Literature DB >> 22090883

Bis(μ(2)-2-amino-5-nitro-benzoato)bis-(2-amino-5-nitro-benzoato)octa-butyldi-μ(3)-oxido-tetra-tin(IV).

Yip-Foo Win, Chen-Shang Choong, Siang-Guan Teoh, Chin Sing Yeap, Hoong-Kun Fun.   

Abstract

In the title complex, [Sn(4)(C(4)H(9))(8)(C(7)H(5)N(2)O(4))(4)O(2)], all four Sn(IV) atoms are five-coordinated with distorted trigonal-bipyramidal SnC(2)O(3) geometries. Two Sn(IV) atoms are coordin-ated by two butyl groups, one benzoate O atom and two bridging O atoms, whereas the other two Sn(IV) atoms are coordinated by two butyl groups, two benzoate O atoms and a bridging O atom. All the butyl groups are equatorial with respect to the SnO(3) trigonal plane. In the crystal, mol-ecules are linked into a two-dimensional layer parallel to the ab plane by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds and further stabilized by a π-π inter-action [centroid-centroid distance = 3.6489 (11) Å]. Intra-molecular N-H⋯O and C-H⋯O hydrogen bonds stabilize the mol-ecular structure. Two of the butyl groups are each disordered over two sets of sites with site-occupancy ratios of 0.510 (4):0.490 (4) and 0.860 (5):0.140 (5).

Entities:  

Year:  2011        PMID: 22090883      PMCID: PMC3212181          DOI: 10.1107/S1600536811028212

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For general background to the title complex, see: Win et al. (2006 ▶); Win, Teoh et al. (2011 ▶). For closely related structures, see: Win et al. (2008 ▶); Win, Choong, Ha et al. (2010 ▶); Win, Choong et al. (2011 ▶); Win, Choong, Teoh et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

[Sn4(C4H9)8(C7H5N2O4)4O2] M = 1688.18 Triclinic, a = 14.3292 (2) Å b = 15.3691 (2) Å c = 18.2096 (2) Å α = 80.289 (1)° β = 74.982 (1)° γ = 65.631 (1)° V = 3519.49 (8) Å3 Z = 2 Mo Kα radiation μ = 1.47 mm−1 T = 100 K 0.45 × 0.19 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.554, T max = 0.899 110407 measured reflections 29672 independent reflections 23074 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.073 S = 1.04 29672 reflections 906 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 2.67 e Å−3 Δρmin = −1.48 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028212/is2746sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028212/is2746Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Sn4(C4H9)8(C7H5N2O4)4O2]Z = 2
Mr = 1688.18F(000) = 1704
Triclinic, P1Dx = 1.593 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 14.3292 (2) ÅCell parameters from 9105 reflections
b = 15.3691 (2) Åθ = 2.3–34.5°
c = 18.2096 (2) ŵ = 1.47 mm1
α = 80.289 (1)°T = 100 K
β = 74.982 (1)°Block, yellow
γ = 65.631 (1)°0.45 × 0.19 × 0.07 mm
V = 3519.49 (8) Å3
Bruker SMART APEXII CCD area-detector diffractometer29672 independent reflections
Radiation source: fine-focus sealed tube23074 reflections with I > 2σ(I)
graphiteRint = 0.030
φ and ω scansθmax = 34.7°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −21→22
Tmin = 0.554, Tmax = 0.899k = −24→24
110407 measured reflectionsl = −29→29
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0254P)2 + 2.328P] where P = (Fo2 + 2Fc2)/3
29672 reflections(Δ/σ)max = 0.003
906 parametersΔρmax = 2.67 e Å3
0 restraintsΔρmin = −1.48 e Å3
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/UeqOcc. (<1)
Sn10.615883 (9)0.312195 (8)0.235446 (7)0.01671 (3)
Sn20.844716 (8)0.170539 (8)0.276260 (7)0.01463 (3)
Sn30.726881 (9)0.058100 (8)0.183349 (8)0.01861 (3)
Sn40.737168 (9)0.429485 (8)0.317647 (7)0.01379 (2)
O10.72397 (9)0.17492 (8)0.22430 (8)0.0187 (2)
O20.73553 (9)0.30762 (8)0.28821 (7)0.0172 (2)
O30.54677 (10)0.12840 (9)0.19435 (8)0.0225 (3)
O40.52363 (11)0.28179 (10)0.16622 (10)0.0287 (3)
O50.06846 (11)0.48611 (11)0.12433 (10)0.0354 (4)
O60.20536 (12)0.51919 (10)0.11020 (9)0.0289 (3)
O70.89082 (10)0.00652 (9)0.19418 (8)0.0192 (2)
O80.88365 (10)−0.11355 (10)0.14687 (8)0.0242 (3)
O91.21758 (12)−0.00267 (10)0.22356 (9)0.0292 (3)
O101.35710 (11)−0.13356 (11)0.21556 (9)0.0318 (3)
O110.92936 (10)0.20281 (9)0.35023 (7)0.0187 (2)
O120.91575 (10)0.35208 (9)0.31013 (8)0.0190 (2)
O131.24913 (12)−0.04123 (10)0.39659 (9)0.0298 (3)
O141.39161 (12)−0.01430 (11)0.37262 (10)0.0353 (4)
O150.57450 (9)0.48247 (9)0.30492 (7)0.0176 (2)
O160.58029 (10)0.60183 (9)0.35400 (7)0.0195 (2)
O170.24990 (12)0.48413 (11)0.27848 (10)0.0312 (3)
O180.10145 (12)0.59988 (12)0.31533 (11)0.0367 (4)
N10.16269 (12)0.46123 (12)0.12192 (10)0.0225 (3)
N20.39713 (13)0.07371 (11)0.18058 (10)0.0211 (3)
N31.26428 (12)−0.08903 (12)0.21179 (9)0.0211 (3)
N41.04704 (14)−0.28197 (12)0.14185 (11)0.0248 (3)
N51.29631 (13)0.01373 (12)0.37831 (10)0.0235 (3)
N61.07285 (13)0.40233 (12)0.31479 (10)0.0212 (3)
N70.19774 (13)0.56302 (12)0.30606 (10)0.0254 (3)
N80.40377 (14)0.75500 (12)0.39207 (10)0.0229 (3)
C10.49264 (14)0.21414 (13)0.17427 (11)0.0194 (3)
C20.38675 (13)0.23784 (12)0.15991 (10)0.0155 (3)
C30.32634 (13)0.33358 (12)0.14445 (10)0.0166 (3)
H3A0.35450.38070.14090.020*
C40.22574 (13)0.36082 (12)0.13420 (10)0.0181 (3)
C50.18189 (14)0.29339 (14)0.13872 (11)0.0208 (3)
H5A0.11220.31310.13220.025*
C60.24094 (14)0.19865 (13)0.15260 (11)0.0197 (3)
H6A0.21210.15250.15420.024*
C70.34398 (13)0.16758 (12)0.16469 (10)0.0163 (3)
C80.93483 (13)−0.07913 (12)0.17050 (11)0.0181 (3)
C91.04682 (13)−0.13431 (12)0.17266 (10)0.0165 (3)
C101.10336 (13)−0.08855 (12)0.19018 (10)0.0164 (3)
H10A1.0698−0.02290.20070.020*
C111.20830 (13)−0.13792 (13)0.19243 (10)0.0178 (3)
C121.26059 (14)−0.23398 (13)0.17577 (11)0.0214 (4)
H12A1.3328−0.26680.17680.026*
C131.20658 (15)−0.28020 (13)0.15796 (11)0.0222 (4)
H13A1.2423−0.34530.14610.027*
C141.09805 (14)−0.23306 (12)0.15676 (10)0.0185 (3)
C150.96620 (13)0.26731 (12)0.33423 (10)0.0156 (3)
C161.07532 (13)0.24094 (12)0.34266 (10)0.0153 (3)
C171.13392 (13)0.14435 (12)0.35820 (10)0.0164 (3)
H17A1.10250.09900.36530.020*
C181.23695 (14)0.11414 (13)0.36337 (10)0.0193 (3)
C191.28521 (14)0.17921 (14)0.35424 (11)0.0219 (4)
H19A1.35650.15730.35770.026*
C201.22869 (14)0.27455 (14)0.34031 (11)0.0202 (3)
H20A1.26070.31890.33590.024*
C211.12296 (13)0.30873 (13)0.33225 (10)0.0164 (3)
C220.52883 (13)0.56598 (12)0.33300 (10)0.0159 (3)
C230.41350 (13)0.61543 (12)0.34005 (10)0.0155 (3)
C240.35931 (14)0.57013 (12)0.31860 (10)0.0178 (3)
H24A0.39670.50970.29740.021*
C250.25170 (14)0.61226 (13)0.32779 (11)0.0192 (3)
C260.19400 (14)0.70151 (14)0.35846 (11)0.0225 (4)
H26A0.11980.72940.36510.027*
C270.24589 (14)0.74797 (13)0.37865 (11)0.0216 (4)
H27A0.20700.80890.39880.026*
C280.35682 (13)0.70719 (12)0.37021 (10)0.0173 (3)
C290.64551 (14)0.39952 (12)0.13608 (11)0.0191 (3)
H29A0.70140.41930.14040.023*
H29B0.67290.36020.09160.023*
C300.55173 (14)0.48939 (13)0.12021 (11)0.0201 (3)
H30A0.52820.53250.16180.024*
H30B0.49330.47110.11970.024*
C310.57773 (16)0.54309 (13)0.04414 (11)0.0228 (4)
H31A0.64200.55380.04190.027*
H31B0.59230.50300.00210.027*
C320.48907 (18)0.63928 (15)0.03270 (12)0.0308 (5)
H32A0.50510.6668−0.01930.046*
H32B0.48180.68290.06930.046*
H32C0.42340.62990.04070.046*
C330.5020 (6)0.2954 (5)0.3247 (3)0.0172 (10)0.510 (4)
H33A0.43370.34580.31750.021*0.510 (4)
H33B0.49890.23290.32190.021*0.510 (4)
C340.5145 (3)0.2996 (3)0.4045 (2)0.0198 (8)0.510 (4)
H34A0.49130.36740.41510.024*0.510 (4)
H34B0.58950.26690.40680.024*0.510 (4)
C350.4506 (3)0.2521 (3)0.4662 (2)0.0222 (8)0.510 (4)
H35A0.44450.27260.51650.027*0.510 (4)
H35B0.37900.27530.45660.027*0.510 (4)
C360.4977 (4)0.1437 (3)0.4690 (3)0.0334 (11)0.510 (4)
H36A0.45050.11850.50660.050*0.510 (4)
H36B0.56570.11970.48370.050*0.510 (4)
H36C0.50740.12260.41870.050*0.510 (4)
C33X0.5016 (6)0.3117 (5)0.3451 (4)0.0197 (11)0.490 (4)
H33C0.50490.35250.38020.024*0.490 (4)
H33D0.42970.33900.33540.024*0.490 (4)
C34X0.5250 (3)0.2105 (3)0.3824 (2)0.0204 (8)0.490 (4)
H34C0.59760.18290.39050.025*0.490 (4)
H34D0.52040.17040.34730.025*0.490 (4)
C35X0.4502 (4)0.2068 (3)0.4586 (2)0.0246 (9)0.490 (4)
H35C0.46020.24080.49560.030*0.490 (4)
H35D0.37700.24040.45170.030*0.490 (4)
C36X0.4675 (4)0.1043 (3)0.4908 (3)0.0313 (10)0.490 (4)
H36D0.41420.10510.53730.047*0.490 (4)
H36E0.53730.07280.50270.047*0.490 (4)
H36F0.46200.06910.45300.047*0.490 (4)
C370.96067 (14)0.18908 (13)0.18150 (10)0.0191 (3)
H37A0.96010.25350.18240.023*
H37B1.03000.14190.18970.023*
C380.95222 (16)0.17938 (15)0.10179 (11)0.0244 (4)
H38A0.87780.21040.09780.029*
H38B0.97700.11070.09360.029*
C391.01647 (16)0.22486 (15)0.03967 (11)0.0261 (4)
H39A1.08700.20420.05070.031*
H39B1.02550.2008−0.00990.031*
C400.96720 (18)0.33400 (15)0.03267 (12)0.0296 (4)
H40A1.01270.3583−0.00750.044*
H40B0.95880.35860.08120.044*
H40C0.89850.35520.01980.044*
C410.82967 (14)0.06716 (13)0.36786 (11)0.0199 (3)
H41A0.79550.09980.41590.024*
H41B0.78380.03820.35880.024*
C420.93581 (15)−0.01281 (13)0.37689 (11)0.0240 (4)
H42A0.9678−0.04760.32980.029*
H42B0.98300.01680.38260.029*
C430.92831 (17)−0.08493 (14)0.44502 (11)0.0259 (4)
H43A1.0000−0.12740.45160.031*
H43B0.8913−0.04970.49160.031*
C440.8716 (2)−0.14621 (16)0.43712 (14)0.0355 (5)
H44A0.8760−0.19490.47990.053*
H44B0.9043−0.17760.38910.053*
H44C0.7979−0.10570.43730.053*
C450.68765 (15)−0.03894 (13)0.27141 (12)0.0231 (4)
H45A0.7491−0.07680.29470.028*
H45B0.6299−0.00200.31150.028*
C460.65399 (16)−0.10772 (13)0.24266 (13)0.0256 (4)
H46A0.5888−0.07000.22370.031*
H46B0.7090−0.14000.19920.031*
C470.63512 (16)−0.18382 (14)0.30332 (13)0.0287 (4)
H47A0.5859−0.15180.34900.034*
H47B0.6013−0.21710.28370.034*
C480.7341 (2)−0.25768 (16)0.32661 (15)0.0371 (5)
H48A0.7178−0.30860.36050.056*
H48B0.7624−0.22700.35330.056*
H48C0.7862−0.28520.28110.056*
C490.75241 (19)0.08989 (19)0.06048 (14)0.0246 (5)0.860 (5)
H49A0.69550.15120.04950.030*0.860 (5)
H49C0.81900.09980.04340.030*0.860 (5)
C500.75720 (19)0.01522 (19)0.01225 (14)0.0287 (6)0.860 (5)
H50A0.78070.0332−0.04210.034*0.860 (5)
H50B0.8109−0.04730.02540.034*0.860 (5)
C510.6545 (2)0.00274 (17)0.02148 (15)0.0274 (6)0.860 (5)
H51A0.6681−0.0519−0.00730.033*0.860 (5)
H51B0.6298−0.01350.07600.033*0.860 (5)
C520.5679 (2)0.0905 (2)−0.00562 (17)0.0287 (6)0.860 (5)
H52A0.50550.07640.00040.043*0.860 (5)
H52B0.59170.1077−0.05950.043*0.860 (5)
H52C0.55070.14410.02470.043*0.860 (5)
C49X0.7335 (13)0.0636 (12)0.0793 (9)0.023 (3)*0.140 (5)
H49B0.68810.12900.06330.028*0.140 (5)
H49D0.80630.05270.05200.028*0.140 (5)
C50X0.7001 (13)−0.0089 (11)0.0539 (9)0.029 (3)*0.140 (5)
H50C0.7556−0.07340.05880.035*0.140 (5)
H50D0.6357−0.00930.09050.035*0.140 (5)
C51X0.6803 (13)0.0057 (12)−0.0225 (10)0.030 (4)*0.140 (5)
H51C0.6740−0.0521−0.03420.035*0.140 (5)
H51D0.74100.0134−0.05960.035*0.140 (5)
C52X0.5818 (17)0.0924 (16)−0.0327 (11)0.029 (3)*0.140 (5)
H52D0.56580.0920−0.08180.043*0.140 (5)
H52E0.59280.1509−0.03160.043*0.140 (5)
H52F0.52310.09030.00860.043*0.140 (5)
C530.71291 (16)0.41534 (15)0.43874 (11)0.0243 (4)
H53A0.64130.41690.45990.029*
H53B0.76280.35160.45400.029*
C540.72566 (16)0.49149 (16)0.47538 (11)0.0273 (4)
H54A0.67360.55510.46230.033*
H54B0.70960.47940.53150.033*
C550.83427 (17)0.49452 (16)0.45111 (13)0.0299 (4)
H55A0.84770.51300.39580.036*
H55B0.88710.42950.45960.036*
C560.8481 (2)0.56420 (19)0.49380 (14)0.0392 (6)
H56A0.91910.56330.47530.059*
H56B0.83740.54510.54850.059*
H56C0.79680.62900.48510.059*
C570.79555 (14)0.50760 (13)0.22150 (10)0.0197 (3)
H57A0.84250.52990.23750.024*
H57B0.83970.46170.18210.024*
C580.71941 (15)0.59374 (12)0.18323 (10)0.0193 (3)
H58A0.67640.64230.22080.023*
H58B0.67160.57340.16630.023*
C590.77550 (18)0.63886 (16)0.11475 (12)0.0310 (5)
H59A0.81710.59060.07670.037*
H59B0.82480.65730.13160.037*
C600.7005 (2)0.72705 (16)0.07678 (13)0.0352 (5)
H60A0.74100.75550.03570.053*
H60B0.65670.77400.11470.053*
H60C0.65590.70820.05560.053*
H1N20.363 (2)0.0372 (19)0.1916 (15)0.038 (7)*
H2N20.456 (2)0.0581 (17)0.1905 (13)0.026 (6)*
H1N41.078 (2)−0.340 (2)0.1326 (15)0.040 (8)*
H2N40.980 (2)−0.2534 (19)0.1430 (15)0.038 (7)*
H1N61.013 (2)0.4218 (19)0.3087 (15)0.036 (7)*
H2N61.1052 (18)0.4383 (17)0.3072 (13)0.022 (6)*
H1N80.471 (2)0.733 (2)0.3835 (17)0.052 (9)*
H2N80.3716 (19)0.8117 (18)0.3995 (13)0.026 (6)*
U11U22U33U12U13U23
Sn10.01106 (5)0.00921 (5)0.03082 (6)−0.00378 (4)−0.00783 (4)0.00106 (4)
Sn20.01039 (5)0.00965 (5)0.02354 (6)−0.00362 (4)−0.00501 (4)0.00118 (4)
Sn30.01384 (5)0.01048 (5)0.03358 (7)−0.00422 (4)−0.00888 (5)−0.00213 (4)
Sn40.01225 (5)0.01044 (5)0.01863 (5)−0.00414 (4)−0.00414 (4)−0.00019 (4)
O10.0132 (5)0.0096 (5)0.0352 (7)−0.0031 (4)−0.0103 (5)−0.0016 (5)
O20.0122 (5)0.0095 (5)0.0300 (7)−0.0029 (4)−0.0071 (5)−0.0009 (5)
O30.0150 (6)0.0129 (6)0.0412 (8)−0.0047 (5)−0.0108 (5)−0.0001 (5)
O40.0239 (7)0.0152 (6)0.0561 (10)−0.0105 (5)−0.0225 (7)0.0039 (6)
O50.0163 (7)0.0268 (8)0.0557 (10)−0.0004 (6)−0.0130 (7)0.0038 (7)
O60.0260 (7)0.0141 (6)0.0465 (9)−0.0047 (5)−0.0120 (7)−0.0034 (6)
O70.0150 (6)0.0118 (5)0.0305 (7)−0.0029 (5)−0.0072 (5)−0.0028 (5)
O80.0184 (6)0.0190 (6)0.0383 (8)−0.0052 (5)−0.0114 (6)−0.0070 (6)
O90.0282 (7)0.0197 (7)0.0452 (9)−0.0120 (6)−0.0137 (7)0.0000 (6)
O100.0183 (7)0.0346 (8)0.0457 (9)−0.0115 (6)−0.0109 (6)−0.0014 (7)
O110.0170 (6)0.0166 (6)0.0257 (6)−0.0091 (5)−0.0081 (5)0.0027 (5)
O120.0148 (5)0.0136 (5)0.0292 (7)−0.0051 (5)−0.0077 (5)0.0010 (5)
O130.0268 (7)0.0164 (6)0.0403 (9)−0.0028 (6)−0.0073 (6)−0.0010 (6)
O140.0189 (7)0.0288 (8)0.0527 (10)0.0016 (6)−0.0157 (7)−0.0049 (7)
O150.0135 (5)0.0126 (5)0.0245 (6)−0.0029 (4)−0.0040 (5)−0.0013 (5)
O160.0149 (6)0.0186 (6)0.0253 (6)−0.0057 (5)−0.0052 (5)−0.0030 (5)
O170.0296 (8)0.0225 (7)0.0483 (9)−0.0140 (6)−0.0121 (7)−0.0035 (6)
O180.0198 (7)0.0330 (9)0.0632 (11)−0.0131 (6)−0.0149 (7)−0.0009 (8)
N10.0182 (7)0.0172 (7)0.0284 (8)−0.0021 (6)−0.0064 (6)−0.0019 (6)
N20.0176 (7)0.0142 (7)0.0353 (9)−0.0083 (6)−0.0099 (6)0.0012 (6)
N30.0179 (7)0.0217 (8)0.0257 (8)−0.0104 (6)−0.0060 (6)0.0025 (6)
N40.0228 (8)0.0132 (7)0.0401 (10)−0.0026 (6)−0.0136 (7)−0.0065 (7)
N50.0187 (7)0.0214 (8)0.0262 (8)−0.0006 (6)−0.0086 (6)−0.0039 (6)
N60.0181 (7)0.0163 (7)0.0325 (9)−0.0092 (6)−0.0075 (6)−0.0002 (6)
N70.0213 (8)0.0211 (8)0.0379 (9)−0.0120 (7)−0.0109 (7)0.0047 (7)
N80.0176 (7)0.0150 (7)0.0351 (9)−0.0025 (6)−0.0075 (7)−0.0068 (6)
C10.0143 (7)0.0143 (7)0.0312 (9)−0.0056 (6)−0.0076 (7)−0.0013 (7)
C20.0132 (7)0.0138 (7)0.0206 (8)−0.0055 (6)−0.0040 (6)−0.0023 (6)
C30.0155 (7)0.0133 (7)0.0222 (8)−0.0054 (6)−0.0058 (6)−0.0021 (6)
C40.0151 (7)0.0149 (7)0.0225 (8)−0.0026 (6)−0.0062 (6)−0.0017 (6)
C50.0142 (7)0.0215 (8)0.0284 (9)−0.0075 (7)−0.0081 (7)0.0007 (7)
C60.0164 (8)0.0193 (8)0.0274 (9)−0.0099 (7)−0.0069 (7)−0.0002 (7)
C70.0144 (7)0.0163 (7)0.0191 (8)−0.0067 (6)−0.0040 (6)−0.0011 (6)
C80.0143 (7)0.0135 (7)0.0253 (8)−0.0031 (6)−0.0058 (6)−0.0018 (6)
C90.0146 (7)0.0119 (7)0.0207 (8)−0.0020 (6)−0.0050 (6)−0.0018 (6)
C100.0155 (7)0.0135 (7)0.0198 (8)−0.0056 (6)−0.0040 (6)0.0002 (6)
C110.0153 (7)0.0175 (8)0.0206 (8)−0.0067 (6)−0.0047 (6)0.0012 (6)
C120.0150 (8)0.0193 (8)0.0266 (9)−0.0031 (7)−0.0060 (7)−0.0002 (7)
C130.0189 (8)0.0143 (8)0.0299 (9)−0.0008 (7)−0.0076 (7)−0.0031 (7)
C140.0195 (8)0.0123 (7)0.0230 (8)−0.0037 (6)−0.0076 (6)−0.0013 (6)
C150.0123 (7)0.0147 (7)0.0201 (8)−0.0051 (6)−0.0045 (6)−0.0003 (6)
C160.0129 (7)0.0151 (7)0.0190 (7)−0.0057 (6)−0.0046 (6)−0.0012 (6)
C170.0153 (7)0.0149 (7)0.0194 (8)−0.0054 (6)−0.0051 (6)−0.0016 (6)
C180.0152 (7)0.0176 (8)0.0230 (8)−0.0027 (6)−0.0066 (6)−0.0021 (6)
C190.0143 (7)0.0263 (9)0.0260 (9)−0.0068 (7)−0.0067 (7)−0.0033 (7)
C200.0157 (8)0.0220 (8)0.0258 (9)−0.0092 (7)−0.0048 (6)−0.0031 (7)
C210.0144 (7)0.0182 (8)0.0183 (7)−0.0074 (6)−0.0030 (6)−0.0031 (6)
C220.0132 (7)0.0140 (7)0.0179 (7)−0.0038 (6)−0.0033 (6)0.0013 (6)
C230.0135 (7)0.0129 (7)0.0191 (7)−0.0044 (6)−0.0045 (6)0.0014 (6)
C240.0177 (8)0.0135 (7)0.0217 (8)−0.0065 (6)−0.0046 (6)0.0020 (6)
C250.0171 (8)0.0171 (8)0.0261 (9)−0.0086 (6)−0.0076 (7)0.0021 (7)
C260.0142 (8)0.0203 (8)0.0308 (10)−0.0054 (7)−0.0047 (7)0.0009 (7)
C270.0161 (8)0.0162 (8)0.0300 (9)−0.0032 (6)−0.0046 (7)−0.0039 (7)
C280.0148 (7)0.0140 (7)0.0214 (8)−0.0038 (6)−0.0040 (6)−0.0010 (6)
C290.0180 (8)0.0146 (7)0.0261 (9)−0.0065 (6)−0.0077 (7)−0.0004 (6)
C300.0196 (8)0.0151 (8)0.0262 (9)−0.0070 (7)−0.0070 (7)0.0005 (6)
C310.0262 (9)0.0182 (8)0.0233 (9)−0.0082 (7)−0.0060 (7)0.0005 (7)
C320.0332 (11)0.0211 (9)0.0283 (10)−0.0042 (8)−0.0045 (8)0.0035 (8)
C330.0161 (17)0.014 (2)0.021 (3)−0.0074 (17)−0.002 (2)0.0000 (17)
C340.0210 (16)0.0211 (17)0.0200 (17)−0.0113 (14)−0.0024 (13)−0.0035 (13)
C350.0237 (18)0.024 (2)0.0185 (17)−0.0107 (16)−0.0014 (13)−0.0003 (15)
C360.048 (3)0.025 (2)0.027 (2)−0.015 (2)−0.0102 (19)0.0028 (17)
C33X0.0125 (17)0.015 (2)0.027 (3)−0.0027 (17)0.000 (2)−0.0018 (19)
C34X0.0197 (17)0.0153 (16)0.0261 (19)−0.0076 (14)−0.0041 (14)0.0003 (13)
C35X0.029 (2)0.023 (2)0.024 (2)−0.0128 (19)−0.0037 (16)−0.0020 (17)
C36X0.042 (3)0.029 (2)0.023 (2)−0.018 (2)−0.0073 (18)0.0080 (17)
C370.0159 (7)0.0184 (8)0.0232 (8)−0.0077 (6)−0.0038 (6)0.0009 (6)
C380.0261 (9)0.0242 (9)0.0258 (9)−0.0123 (8)−0.0068 (7)−0.0006 (7)
C390.0259 (9)0.0293 (10)0.0224 (9)−0.0108 (8)−0.0044 (7)−0.0011 (7)
C400.0320 (11)0.0278 (10)0.0268 (10)−0.0112 (9)−0.0062 (8)0.0028 (8)
C410.0183 (8)0.0154 (8)0.0258 (9)−0.0079 (6)−0.0028 (7)0.0000 (6)
C420.0213 (9)0.0173 (8)0.0274 (9)−0.0047 (7)−0.0040 (7)0.0051 (7)
C430.0295 (10)0.0203 (9)0.0247 (9)−0.0088 (8)−0.0053 (8)0.0034 (7)
C440.0478 (14)0.0263 (11)0.0368 (12)−0.0204 (10)−0.0106 (10)0.0049 (9)
C450.0204 (8)0.0138 (8)0.0357 (10)−0.0073 (7)−0.0064 (7)−0.0011 (7)
C460.0223 (9)0.0145 (8)0.0440 (12)−0.0087 (7)−0.0133 (8)0.0014 (8)
C470.0264 (10)0.0191 (9)0.0417 (12)−0.0128 (8)−0.0005 (9)−0.0051 (8)
C480.0464 (14)0.0229 (10)0.0499 (14)−0.0176 (10)−0.0225 (11)0.0072 (10)
C490.0230 (11)0.0272 (12)0.0259 (11)−0.0132 (10)−0.0089 (9)0.0069 (10)
C500.0261 (12)0.0307 (13)0.0248 (11)−0.0045 (10)−0.0083 (9)−0.0031 (9)
C510.0390 (14)0.0191 (10)0.0268 (13)−0.0118 (10)−0.0105 (10)−0.0019 (9)
C520.0288 (13)0.0296 (13)0.0300 (14)−0.0127 (10)−0.0084 (12)−0.0011 (12)
C530.0228 (9)0.0287 (10)0.0202 (8)−0.0104 (8)−0.0058 (7)0.0043 (7)
C540.0264 (10)0.0369 (11)0.0170 (8)−0.0103 (9)−0.0048 (7)−0.0025 (8)
C550.0274 (10)0.0309 (11)0.0320 (11)−0.0074 (9)−0.0096 (8)−0.0086 (9)
C560.0389 (13)0.0441 (14)0.0408 (13)−0.0135 (11)−0.0174 (11)−0.0114 (11)
C570.0194 (8)0.0172 (8)0.0222 (8)−0.0086 (7)−0.0033 (6)0.0021 (6)
C580.0232 (8)0.0140 (7)0.0219 (8)−0.0090 (7)−0.0060 (7)0.0019 (6)
C590.0355 (11)0.0275 (10)0.0287 (10)−0.0159 (9)−0.0051 (9)0.0087 (8)
C600.0564 (15)0.0239 (10)0.0293 (11)−0.0204 (10)−0.0145 (10)0.0088 (8)
Sn1—O12.0436 (12)C33—H33A0.9900
Sn1—C332.050 (7)C33—H33B0.9900
Sn1—C292.1234 (18)C34—C351.541 (5)
Sn1—O22.1445 (12)C34—H34A0.9900
Sn1—C33X2.232 (7)C34—H34B0.9900
Sn1—O42.2643 (14)C35—C361.516 (6)
Sn1—Sn23.29699 (17)C35—H35A0.9900
Sn2—O22.0474 (12)C35—H35B0.9900
Sn2—C412.1343 (18)C36—H36A0.9800
Sn2—C372.1351 (17)C36—H36B0.9800
Sn2—O12.1504 (12)C36—H36C0.9800
Sn2—O112.2583 (13)C33X—C34X1.525 (8)
Sn3—C49X1.861 (16)C33X—H33C0.9900
Sn3—O12.0384 (12)C33X—H33D0.9900
Sn3—C452.1283 (19)C34X—C35X1.527 (6)
Sn3—C492.176 (3)C34X—H34C0.9900
Sn3—O72.1992 (12)C34X—H34D0.9900
Sn3—O32.3178 (13)C35X—C36X1.526 (6)
Sn4—O22.0439 (12)C35X—H35C0.9900
Sn4—C532.1293 (19)C35X—H35D0.9900
Sn4—C572.1370 (17)C36X—H36D0.9800
Sn4—O152.1908 (12)C36X—H36E0.9800
Sn4—O122.3115 (12)C36X—H36F0.9800
O3—C11.270 (2)C37—C381.524 (3)
O4—C11.263 (2)C37—H37A0.9900
O5—N11.233 (2)C37—H37B0.9900
O6—N11.237 (2)C38—C391.530 (3)
O7—C81.297 (2)C38—H38A0.9900
O8—C81.250 (2)C38—H38B0.9900
O9—N31.243 (2)C39—C401.525 (3)
O10—N31.234 (2)C39—H39A0.9900
O11—C151.265 (2)C39—H39B0.9900
O12—C151.268 (2)C40—H40A0.9800
O13—N51.241 (2)C40—H40B0.9800
O14—N51.232 (2)C40—H40C0.9800
O15—C221.301 (2)C41—C421.539 (3)
O16—C221.243 (2)C41—H41A0.9900
O17—N71.243 (2)C41—H41B0.9900
O18—N71.233 (2)C42—C431.531 (3)
N1—C41.444 (2)C42—H42A0.9900
N2—C71.346 (2)C42—H42B0.9900
N2—H1N20.85 (3)C43—C441.519 (3)
N2—H2N20.83 (2)C43—H43A0.9900
N3—C111.437 (2)C43—H43B0.9900
N4—C141.341 (2)C44—H44A0.9800
N4—H1N40.85 (3)C44—H44B0.9800
N4—H2N40.87 (3)C44—H44C0.9800
N5—C181.440 (2)C45—C461.537 (3)
N6—C211.341 (2)C45—H45A0.9900
N6—H1N60.82 (3)C45—H45B0.9900
N6—H2N60.83 (2)C46—C471.527 (3)
N7—C251.439 (2)C46—H46A0.9900
N8—C281.340 (2)C46—H46B0.9900
N8—H1N80.86 (3)C47—C481.517 (3)
N8—H2N80.82 (2)C47—H47A0.9900
C1—C21.490 (2)C47—H47B0.9900
C2—C31.389 (2)C48—H48A0.9800
C2—C71.427 (2)C48—H48B0.9800
C3—C41.380 (2)C48—H48C0.9800
C3—H3A0.9500C49—C501.529 (4)
C4—C51.399 (3)C49—H49A0.9900
C5—C61.367 (3)C49—H49C0.9900
C5—H5A0.9500C50—C511.524 (4)
C6—C71.417 (2)C50—H50A0.9900
C6—H6A0.9500C50—H50B0.9900
C8—C91.481 (2)C51—C521.522 (4)
C9—C101.390 (2)C51—H51A0.9900
C9—C141.430 (2)C51—H51B0.9900
C10—C111.385 (2)C52—H52A0.9800
C10—H10A0.9500C52—H52B0.9800
C11—C121.398 (3)C52—H52C0.9800
C12—C131.368 (3)C49X—C50X1.55 (2)
C12—H12A0.9500C49X—H49B0.9900
C13—C141.424 (3)C49X—H49D0.9900
C13—H13A0.9500C50X—C51X1.46 (2)
C15—C161.488 (2)C50X—H50C0.9900
C16—C171.394 (2)C50X—H50D0.9900
C16—C211.428 (2)C51X—C52X1.52 (3)
C17—C181.377 (2)C51X—H51C0.9900
C17—H17A0.9500C51X—H51D0.9900
C18—C191.400 (3)C52X—H52D0.9800
C19—C201.367 (3)C52X—H52E0.9800
C19—H19A0.9500C52X—H52F0.9800
C20—C211.423 (2)C53—C541.533 (3)
C20—H20A0.9500C53—H53A0.9900
C22—C231.487 (2)C53—H53B0.9900
C23—C241.391 (2)C54—C551.522 (3)
C23—C281.427 (2)C54—H54A0.9900
C24—C251.380 (2)C54—H54B0.9900
C24—H24A0.9500C55—C561.525 (3)
C25—C261.400 (3)C55—H55A0.9900
C26—C271.366 (3)C55—H55B0.9900
C26—H26A0.9500C56—H56A0.9800
C27—C281.424 (2)C56—H56B0.9800
C27—H27A0.9500C56—H56C0.9800
C29—C301.527 (2)C57—C581.523 (2)
C29—H29A0.9900C57—H57A0.9900
C29—H29B0.9900C57—H57B0.9900
C30—C311.530 (3)C58—C591.527 (3)
C30—H30A0.9900C58—H58A0.9900
C30—H30B0.9900C58—H58B0.9900
C31—C321.525 (3)C59—C601.528 (3)
C31—H31A0.9900C59—H59A0.9900
C31—H31B0.9900C59—H59B0.9900
C32—H32A0.9800C60—H60A0.9800
C32—H32B0.9800C60—H60B0.9800
C32—H32C0.9800C60—H60C0.9800
C33—C341.526 (6)
O1—Sn1—C33102.26 (19)C34—C33—Sn1116.7 (4)
O1—Sn1—C29109.79 (6)C34—C33—H33A108.1
C33—Sn1—C29144.4 (2)Sn1—C33—H33A108.1
O1—Sn1—O276.44 (5)C34—C33—H33B108.1
C33—Sn1—O2104.49 (17)Sn1—C33—H33B108.1
C29—Sn1—O297.91 (6)H33A—C33—H33B107.3
O1—Sn1—C33X106.93 (18)C33—C34—C35112.0 (4)
C33—Sn1—C33X11.9 (2)C33—C34—H34A109.2
C29—Sn1—C33X143.02 (19)C35—C34—H34A109.2
O2—Sn1—C33X94.69 (18)C33—C34—H34B109.2
O1—Sn1—O489.08 (5)C35—C34—H34B109.2
C33—Sn1—O482.72 (16)H34A—C34—H34B107.9
C29—Sn1—O482.63 (6)C36—C35—C34113.9 (3)
O2—Sn1—O4164.84 (5)C36—C35—H35A108.8
C33X—Sn1—O493.80 (17)C34—C35—H35A108.8
O1—Sn1—Sn239.34 (3)C36—C35—H35B108.8
C33—Sn1—Sn2107.5 (2)C34—C35—H35B108.8
C29—Sn1—Sn2107.14 (5)H35A—C35—H35B107.7
O2—Sn1—Sn237.11 (3)C34X—C33X—Sn1111.2 (4)
C33X—Sn1—Sn2103.85 (19)C34X—C33X—H33C109.4
O4—Sn1—Sn2128.23 (4)Sn1—C33X—H33C109.4
O2—Sn2—C41116.69 (6)C34X—C33X—H33D109.4
O2—Sn2—C37102.20 (6)Sn1—C33X—H33D109.4
C41—Sn2—C37139.14 (7)H33C—C33X—H33D108.0
O2—Sn2—O176.23 (5)C33X—C34X—C35X113.1 (4)
C41—Sn2—O197.59 (6)C33X—C34X—H34C109.0
C37—Sn2—O1103.59 (6)C35X—C34X—H34C109.0
O2—Sn2—O1187.60 (5)C33X—C34X—H34D109.0
C41—Sn2—O1183.03 (6)C35X—C34X—H34D109.0
C37—Sn2—O1186.75 (6)H34C—C34X—H34D107.8
O1—Sn2—O11162.25 (5)C36X—C35X—C34X112.2 (4)
O2—Sn2—Sn139.19 (3)C36X—C35X—H35C109.2
C41—Sn2—Sn1111.68 (5)C34X—C35X—H35C109.2
C37—Sn2—Sn1106.18 (5)C36X—C35X—H35D109.2
O1—Sn2—Sn137.04 (3)C34X—C35X—H35D109.2
O11—Sn2—Sn1126.47 (3)H35C—C35X—H35D107.9
C49X—Sn3—O1117.0 (5)C35X—C36X—H36D109.5
C49X—Sn3—C45128.7 (6)C35X—C36X—H36E109.5
O1—Sn3—C45112.74 (7)H36D—C36X—H36E109.5
C49X—Sn3—C4914.3 (5)C35X—C36X—H36F109.5
O1—Sn3—C49103.90 (8)H36D—C36X—H36F109.5
C45—Sn3—C49142.79 (9)H36E—C36X—H36F109.5
C49X—Sn3—O7105.0 (5)C38—C37—Sn2118.39 (13)
O1—Sn3—O779.83 (5)C38—C37—H37A107.7
C45—Sn3—O794.91 (6)Sn2—C37—H37A107.7
C49—Sn3—O797.73 (7)C38—C37—H37B107.7
C49X—Sn3—O385.3 (5)Sn2—C37—H37B107.7
O1—Sn3—O390.46 (5)H37A—C37—H37B107.1
C45—Sn3—O382.56 (6)C37—C38—C39112.21 (16)
C49—Sn3—O391.11 (7)C37—C38—H38A109.2
O7—Sn3—O3168.18 (5)C39—C38—H38A109.2
O2—Sn4—C53105.16 (7)C37—C38—H38B109.2
O2—Sn4—C57112.18 (6)C39—C38—H38B109.2
C53—Sn4—C57140.54 (8)H38A—C38—H38B107.9
O2—Sn4—O1580.07 (5)C40—C39—C38113.81 (17)
C53—Sn4—O1599.69 (6)C40—C39—H39A108.8
C57—Sn4—O1598.85 (6)C38—C39—H39A108.8
O2—Sn4—O1289.13 (5)C40—C39—H39B108.8
C53—Sn4—O1289.47 (6)C38—C39—H39B108.8
C57—Sn4—O1279.01 (6)H39A—C39—H39B107.7
O15—Sn4—O12167.33 (5)C39—C40—H40A109.5
Sn3—O1—Sn1133.09 (6)C39—C40—H40B109.5
Sn3—O1—Sn2123.16 (6)H40A—C40—H40B109.5
Sn1—O1—Sn2103.62 (5)C39—C40—H40C109.5
Sn4—O2—Sn2133.50 (6)H40A—C40—H40C109.5
Sn4—O2—Sn1121.48 (6)H40B—C40—H40C109.5
Sn2—O2—Sn1103.70 (5)C42—C41—Sn2112.73 (12)
C1—O3—Sn3127.34 (12)C42—C41—H41A109.0
C1—O4—Sn1130.17 (13)Sn2—C41—H41A109.0
C8—O7—Sn3105.06 (11)C42—C41—H41B109.0
C15—O11—Sn2124.96 (11)Sn2—C41—H41B109.0
C15—O12—Sn4128.32 (11)H41A—C41—H41B107.8
C22—O15—Sn4105.22 (11)C43—C42—C41113.99 (16)
O5—N1—O6122.51 (16)C43—C42—H42A108.8
O5—N1—C4118.98 (17)C41—C42—H42A108.8
O6—N1—C4118.51 (15)C43—C42—H42B108.8
C7—N2—H1N2117.9 (18)C41—C42—H42B108.8
C7—N2—H2N2116.8 (17)H42A—C42—H42B107.6
H1N2—N2—H2N2123 (2)C44—C43—C42113.81 (18)
O10—N3—O9122.07 (17)C44—C43—H43A108.8
O10—N3—C11119.24 (16)C42—C43—H43A108.8
O9—N3—C11118.69 (15)C44—C43—H43B108.8
C14—N4—H1N4121.5 (19)C42—C43—H43B108.8
C14—N4—H2N4119.3 (18)H43A—C43—H43B107.7
H1N4—N4—H2N4119 (3)C43—C44—H44A109.5
O14—N5—O13122.57 (17)C43—C44—H44B109.5
O14—N5—C18118.92 (18)H44A—C44—H44B109.5
O13—N5—C18118.51 (16)C43—C44—H44C109.5
C21—N6—H1N6119.1 (19)H44A—C44—H44C109.5
C21—N6—H2N6119.1 (16)H44B—C44—H44C109.5
H1N6—N6—H2N6122 (2)C46—C45—Sn3112.88 (14)
O18—N7—O17121.85 (18)C46—C45—H45A109.0
O18—N7—C25119.37 (17)Sn3—C45—H45A109.0
O17—N7—C25118.78 (16)C46—C45—H45B109.0
C28—N8—H1N8119 (2)Sn3—C45—H45B109.0
C28—N8—H2N8119.4 (17)H45A—C45—H45B107.8
H1N8—N8—H2N8118 (3)C47—C46—C45113.72 (18)
O4—C1—O3123.22 (16)C47—C46—H46A108.8
O4—C1—C2117.46 (15)C45—C46—H46A108.8
O3—C1—C2119.32 (16)C47—C46—H46B108.8
C3—C2—C7119.34 (15)C45—C46—H46B108.8
C3—C2—C1117.60 (15)H46A—C46—H46B107.7
C7—C2—C1123.00 (15)C48—C47—C46113.82 (18)
C4—C3—C2120.50 (16)C48—C47—H47A108.8
C4—C3—H3A119.8C46—C47—H47A108.8
C2—C3—H3A119.8C48—C47—H47B108.8
C3—C4—C5121.30 (16)C46—C47—H47B108.8
C3—C4—N1119.43 (16)H47A—C47—H47B107.7
C5—C4—N1119.22 (16)C47—C48—H48A109.5
C6—C5—C4118.96 (16)C47—C48—H48B109.5
C6—C5—H5A120.5H48A—C48—H48B109.5
C4—C5—H5A120.5C47—C48—H48C109.5
C5—C6—C7121.66 (17)H48A—C48—H48C109.5
C5—C6—H6A119.2H48B—C48—H48C109.5
C7—C6—H6A119.2C50—C49—Sn3116.96 (18)
N2—C7—C6119.03 (16)C50—C49—H49A108.1
N2—C7—C2122.75 (16)Sn3—C49—H49A108.1
C6—C7—C2118.22 (15)C50—C49—H49C108.1
O8—C8—O7120.61 (16)Sn3—C49—H49C108.1
O8—C8—C9121.48 (16)H49A—C49—H49C107.3
O7—C8—C9117.90 (16)C51—C50—C49115.3 (2)
C10—C9—C14119.38 (16)C51—C50—H50A108.4
C10—C9—C8119.00 (15)C49—C50—H50A108.4
C14—C9—C8121.61 (16)C51—C50—H50B108.4
C11—C10—C9120.51 (16)C49—C50—H50B108.4
C11—C10—H10A119.7H50A—C50—H50B107.5
C9—C10—H10A119.7C52—C51—C50114.2 (2)
C10—C11—C12121.17 (17)C52—C51—H51A108.7
C10—C11—N3119.22 (16)C50—C51—H51A108.7
C12—C11—N3119.61 (16)C52—C51—H51B108.7
C13—C12—C11119.26 (17)C50—C51—H51B108.7
C13—C12—H12A120.4H51A—C51—H51B107.6
C11—C12—H12A120.4C50X—C49X—Sn3115.6 (12)
C12—C13—C14121.54 (17)C50X—C49X—H49B108.4
C12—C13—H13A119.2Sn3—C49X—H49B108.4
C14—C13—H13A119.2C50X—C49X—H49D108.4
N4—C14—C13119.67 (16)Sn3—C49X—H49D108.4
N4—C14—C9122.22 (17)H49B—C49X—H49D107.4
C13—C14—C9118.10 (17)C51X—C50X—C49X118.2 (14)
O11—C15—O12123.40 (15)C51X—C50X—H50C107.8
O11—C15—C16117.83 (15)C49X—C50X—H50C107.8
O12—C15—C16118.76 (15)C51X—C50X—H50D107.8
C17—C16—C21119.43 (15)C49X—C50X—H50D107.8
C17—C16—C15117.28 (15)H50C—C50X—H50D107.1
C21—C16—C15123.23 (15)C50X—C51X—C52X113.3 (15)
C18—C17—C16120.49 (16)C50X—C51X—H51C108.9
C18—C17—H17A119.8C52X—C51X—H51C108.9
C16—C17—H17A119.8C50X—C51X—H51D108.9
C17—C18—C19121.23 (17)C52X—C51X—H51D108.9
C17—C18—N5119.42 (17)H51C—C51X—H51D107.7
C19—C18—N5119.35 (16)C51X—C52X—H52D109.5
C20—C19—C18119.31 (17)C51X—C52X—H52E109.5
C20—C19—H19A120.3H52D—C52X—H52E109.5
C18—C19—H19A120.3C51X—C52X—H52F109.5
C19—C20—C21121.41 (17)H52D—C52X—H52F109.5
C19—C20—H20A119.3H52E—C52X—H52F109.5
C21—C20—H20A119.3C54—C53—Sn4115.86 (13)
N6—C21—C20118.95 (16)C54—C53—H53A108.3
N6—C21—C16122.97 (16)Sn4—C53—H53A108.3
C20—C21—C16118.07 (16)C54—C53—H53B108.3
O16—C22—O15120.67 (15)Sn4—C53—H53B108.3
O16—C22—C23121.77 (16)H53A—C53—H53B107.4
O15—C22—C23117.55 (15)C55—C54—C53114.43 (17)
C24—C23—C28119.26 (16)C55—C54—H54A108.7
C24—C23—C22119.27 (15)C53—C54—H54A108.7
C28—C23—C22121.45 (16)C55—C54—H54B108.7
C25—C24—C23120.59 (16)C53—C54—H54B108.7
C25—C24—H24A119.7H54A—C54—H54B107.6
C23—C24—H24A119.7C54—C55—C56113.45 (19)
C24—C25—C26121.30 (17)C54—C55—H55A108.9
C24—C25—N7119.29 (17)C56—C55—H55A108.9
C26—C25—N7119.41 (16)C54—C55—H55B108.9
C27—C26—C25119.04 (17)C56—C55—H55B108.9
C27—C26—H26A120.5H55A—C55—H55B107.7
C25—C26—H26A120.5C55—C56—H56A109.5
C26—C27—C28121.58 (17)C55—C56—H56B109.5
C26—C27—H27A119.2H56A—C56—H56B109.5
C28—C27—H27A119.2C55—C56—H56C109.5
N8—C28—C27119.23 (16)H56A—C56—H56C109.5
N8—C28—C23122.54 (16)H56B—C56—H56C109.5
C27—C28—C23118.22 (16)C58—C57—Sn4119.96 (12)
C30—C29—Sn1115.88 (12)C58—C57—H57A107.3
C30—C29—H29A108.3Sn4—C57—H57A107.3
Sn1—C29—H29A108.3C58—C57—H57B107.3
C30—C29—H29B108.3Sn4—C57—H57B107.3
Sn1—C29—H29B108.3H57A—C57—H57B106.9
H29A—C29—H29B107.4C57—C58—C59112.36 (16)
C29—C30—C31112.29 (15)C57—C58—H58A109.1
C29—C30—H30A109.1C59—C58—H58A109.1
C31—C30—H30A109.1C57—C58—H58B109.1
C29—C30—H30B109.1C59—C58—H58B109.1
C31—C30—H30B109.1H58A—C58—H58B107.9
H30A—C30—H30B107.9C58—C59—C60113.17 (19)
C32—C31—C30112.46 (16)C58—C59—H59A108.9
C32—C31—H31A109.1C60—C59—H59A108.9
C30—C31—H31A109.1C58—C59—H59B108.9
C32—C31—H31B109.1C60—C59—H59B108.9
C30—C31—H31B109.1H59A—C59—H59B107.8
H31A—C31—H31B107.8C59—C60—H60A109.5
C31—C32—H32A109.5C59—C60—H60B109.5
C31—C32—H32B109.5H60A—C60—H60B109.5
H32A—C32—H32B109.5C59—C60—H60C109.5
C31—C32—H32C109.5H60A—C60—H60C109.5
H32A—C32—H32C109.5H60B—C60—H60C109.5
H32B—C32—H32C109.5
O1—Sn1—Sn2—O2−179.19 (8)Sn3—O7—C8—C9−178.59 (13)
C33—Sn1—Sn2—O2−91.07 (16)O8—C8—C9—C10171.89 (17)
C29—Sn1—Sn2—O280.28 (8)O7—C8—C9—C10−8.3 (3)
C33X—Sn1—Sn2—O2−79.27 (17)O8—C8—C9—C14−7.8 (3)
O4—Sn1—Sn2—O2174.41 (8)O7—C8—C9—C14172.08 (16)
O1—Sn1—Sn2—C41−73.09 (8)C14—C9—C10—C11−0.1 (3)
C33—Sn1—Sn2—C4115.03 (16)C8—C9—C10—C11−179.78 (16)
C29—Sn1—Sn2—C41−173.62 (8)C9—C10—C11—C121.3 (3)
O2—Sn1—Sn2—C41106.10 (8)C9—C10—C11—N3−179.12 (16)
C33X—Sn1—Sn2—C4126.83 (17)O10—N3—C11—C10178.31 (17)
O4—Sn1—Sn2—C41−79.49 (8)O9—N3—C11—C10−2.3 (3)
O1—Sn1—Sn2—C3791.25 (8)O10—N3—C11—C12−2.1 (3)
C33—Sn1—Sn2—C37179.37 (16)O9—N3—C11—C12177.28 (17)
C29—Sn1—Sn2—C37−9.28 (7)C10—C11—C12—C13−0.9 (3)
O2—Sn1—Sn2—C37−89.56 (8)N3—C11—C12—C13179.52 (17)
C33X—Sn1—Sn2—C37−168.83 (17)C11—C12—C13—C14−0.7 (3)
O4—Sn1—Sn2—C3784.85 (7)C12—C13—C14—N4−177.46 (19)
C33—Sn1—Sn2—O188.12 (16)C12—C13—C14—C91.8 (3)
C29—Sn1—Sn2—O1−100.53 (8)C10—C9—C14—N4177.86 (18)
O2—Sn1—Sn2—O1179.19 (8)C8—C9—C14—N4−2.5 (3)
C33X—Sn1—Sn2—O199.92 (17)C10—C9—C14—C13−1.4 (3)
O4—Sn1—Sn2—O1−6.40 (8)C8—C9—C14—C13178.28 (17)
O1—Sn1—Sn2—O11−170.64 (7)Sn2—O11—C15—O1246.4 (2)
C33—Sn1—Sn2—O11−82.52 (16)Sn2—O11—C15—C16−132.19 (13)
C29—Sn1—Sn2—O1188.83 (7)Sn4—O12—C15—O1118.1 (3)
O2—Sn1—Sn2—O118.55 (7)Sn4—O12—C15—C16−163.34 (11)
C33X—Sn1—Sn2—O11−70.72 (16)O11—C15—C16—C178.0 (2)
O4—Sn1—Sn2—O11−177.04 (6)O12—C15—C16—C17−170.66 (16)
C49X—Sn3—O1—Sn167.5 (6)O11—C15—C16—C21−174.90 (16)
C45—Sn3—O1—Sn1−99.67 (10)O12—C15—C16—C216.5 (3)
C49—Sn3—O1—Sn173.72 (11)C21—C16—C17—C18−0.1 (3)
O7—Sn3—O1—Sn1169.24 (10)C15—C16—C17—C18177.10 (16)
O3—Sn3—O1—Sn1−17.54 (10)C16—C17—C18—C190.8 (3)
C49X—Sn3—O1—Sn2−117.4 (6)C16—C17—C18—N5−179.03 (16)
C45—Sn3—O1—Sn275.44 (9)O14—N5—C18—C17170.25 (18)
C49—Sn3—O1—Sn2−111.18 (9)O13—N5—C18—C17−9.9 (3)
O7—Sn3—O1—Sn2−15.65 (7)O14—N5—C18—C19−9.6 (3)
O3—Sn3—O1—Sn2157.57 (8)O13—N5—C18—C19170.24 (18)
C33—Sn1—O1—Sn373.10 (19)C17—C18—C19—C200.3 (3)
C29—Sn1—O1—Sn3−91.06 (10)N5—C18—C19—C20−179.79 (17)
O2—Sn1—O1—Sn3175.28 (11)C18—C19—C20—C21−2.2 (3)
C33X—Sn1—O1—Sn384.4 (2)C19—C20—C21—N6−176.64 (18)
O4—Sn1—O1—Sn3−9.24 (10)C19—C20—C21—C162.9 (3)
Sn2—Sn1—O1—Sn3175.78 (13)C17—C16—C21—N6177.84 (17)
C33—Sn1—O1—Sn2−102.68 (17)C15—C16—C21—N60.8 (3)
C29—Sn1—O1—Sn293.15 (7)C17—C16—C21—C20−1.6 (2)
O2—Sn1—O1—Sn2−0.50 (5)C15—C16—C21—C20−178.71 (16)
C33X—Sn1—O1—Sn2−91.34 (18)Sn4—O15—C22—O165.59 (19)
O4—Sn1—O1—Sn2174.98 (6)Sn4—O15—C22—C23−173.41 (12)
O2—Sn2—O1—Sn3−175.80 (9)O16—C22—C23—C24−177.31 (16)
C41—Sn2—O1—Sn3−60.08 (9)O15—C22—C23—C241.7 (2)
C37—Sn2—O1—Sn384.73 (9)O16—C22—C23—C281.0 (3)
O11—Sn2—O1—Sn3−150.90 (12)O15—C22—C23—C28179.99 (15)
Sn1—Sn2—O1—Sn3−176.32 (12)C28—C23—C24—C25−1.4 (3)
O2—Sn2—O1—Sn10.53 (5)C22—C23—C24—C25176.97 (16)
C41—Sn2—O1—Sn1116.24 (7)C23—C24—C25—C260.3 (3)
C37—Sn2—O1—Sn1−98.95 (7)C23—C24—C25—N7−179.13 (16)
O11—Sn2—O1—Sn125.42 (19)O18—N7—C25—C24178.88 (18)
C53—Sn4—O2—Sn2−80.21 (10)O17—N7—C25—C24−1.0 (3)
C57—Sn4—O2—Sn286.76 (10)O18—N7—C25—C26−0.6 (3)
O15—Sn4—O2—Sn2−177.66 (10)O17—N7—C25—C26179.57 (18)
O12—Sn4—O2—Sn29.00 (9)C24—C25—C26—C270.8 (3)
C53—Sn4—O2—Sn1115.23 (8)N7—C25—C26—C27−179.73 (18)
C57—Sn4—O2—Sn1−77.80 (8)C25—C26—C27—C28−0.9 (3)
O15—Sn4—O2—Sn117.79 (7)C26—C27—C28—N8−178.89 (19)
O12—Sn4—O2—Sn1−155.55 (7)C26—C27—C28—C23−0.2 (3)
C41—Sn2—O2—Sn4101.35 (10)C24—C23—C28—N8179.97 (17)
C37—Sn2—O2—Sn4−65.76 (10)C22—C23—C28—N81.7 (3)
O1—Sn2—O2—Sn4−166.98 (10)C24—C23—C28—C271.3 (3)
O11—Sn2—O2—Sn420.39 (9)C22—C23—C28—C27−176.99 (16)
Sn1—Sn2—O2—Sn4−166.48 (13)O1—Sn1—C29—C30155.96 (12)
C41—Sn2—O2—Sn1−92.16 (8)C33—Sn1—C29—C303.2 (3)
C37—Sn2—O2—Sn1100.72 (7)O2—Sn1—C29—C30−125.67 (13)
O1—Sn2—O2—Sn1−0.50 (5)C33X—Sn1—C29—C30−16.9 (3)
O11—Sn2—O2—Sn1−173.13 (6)O4—Sn1—C29—C3069.62 (13)
O1—Sn1—O2—Sn4169.06 (8)Sn2—Sn1—C29—C30−162.57 (12)
C33—Sn1—O2—Sn4−91.54 (19)Sn1—C29—C30—C31−174.93 (13)
C29—Sn1—O2—Sn460.51 (8)C29—C30—C31—C32−172.63 (17)
C33X—Sn1—O2—Sn4−84.64 (18)O1—Sn1—C33—C3488.2 (4)
O4—Sn1—O2—Sn4151.52 (17)C29—Sn1—C33—C34−117.9 (4)
Sn2—Sn1—O2—Sn4168.53 (11)O2—Sn1—C33—C349.3 (4)
O1—Sn1—O2—Sn20.53 (5)C33X—Sn1—C33—C34−26.2 (14)
C33—Sn1—O2—Sn299.93 (19)O4—Sn1—C33—C34175.7 (4)
C29—Sn1—O2—Sn2−108.02 (7)Sn2—Sn1—C33—C3447.8 (4)
C33X—Sn1—O2—Sn2106.83 (18)Sn1—C33—C34—C35−159.7 (3)
O4—Sn1—O2—Sn2−17.0 (2)C33—C34—C35—C3674.7 (5)
C49X—Sn3—O3—C1−71.8 (6)O1—Sn1—C33X—C34X−4.3 (4)
O1—Sn3—O3—C145.20 (16)C33—Sn1—C33X—C34X64.2 (16)
C45—Sn3—O3—C1158.08 (17)C29—Sn1—C33X—C34X168.7 (2)
C49—Sn3—O3—C1−58.71 (17)O2—Sn1—C33X—C34X−81.5 (4)
O7—Sn3—O3—C179.8 (3)O4—Sn1—C33X—C34X85.9 (4)
O1—Sn1—O4—C151.15 (17)Sn2—Sn1—C33X—C34X−45.0 (4)
C33—Sn1—O4—C1−51.3 (3)Sn1—C33X—C34X—C35X178.7 (3)
C29—Sn1—O4—C1161.25 (18)C33X—C34X—C35X—C36X173.9 (4)
O2—Sn1—O4—C168.2 (3)O2—Sn2—C37—C38−91.62 (14)
C33X—Sn1—O4—C1−55.8 (2)C41—Sn2—C37—C38106.11 (16)
Sn2—Sn1—O4—C155.21 (18)O1—Sn2—C37—C38−13.05 (15)
C49X—Sn3—O7—C8−63.8 (6)O11—Sn2—C37—C38−178.45 (14)
O1—Sn3—O7—C8−179.24 (12)Sn1—Sn2—C37—C38−51.34 (15)
C45—Sn3—O7—C868.50 (12)Sn2—C37—C38—C39161.63 (13)
C49—Sn3—O7—C8−76.41 (13)C37—C38—C39—C40−74.9 (2)
O3—Sn3—O7—C8145.6 (2)O2—Sn2—C41—C42−149.51 (13)
O2—Sn2—O11—C15−60.74 (14)C37—Sn2—C41—C4211.0 (2)
C41—Sn2—O11—C15−178.00 (14)O1—Sn2—C41—C42132.12 (14)
C37—Sn2—O11—C1541.63 (14)O11—Sn2—C41—C42−65.76 (14)
O1—Sn2—O11—C15−84.9 (2)Sn1—Sn2—C41—C42167.68 (12)
Sn1—Sn2—O11—C15−66.14 (14)Sn2—C41—C42—C43176.64 (14)
O2—Sn4—O12—C15−42.71 (15)C41—C42—C43—C4467.4 (2)
C53—Sn4—O12—C1562.47 (16)C49X—Sn3—C45—C46−4.4 (6)
C57—Sn4—O12—C15−155.51 (16)O1—Sn3—C45—C46160.89 (12)
O15—Sn4—O12—C15−74.1 (3)C49—Sn3—C45—C46−8.4 (2)
O2—Sn4—O15—C22168.90 (11)O7—Sn3—C45—C46−118.09 (13)
C53—Sn4—O15—C2265.04 (12)O3—Sn3—C45—C4673.53 (13)
C57—Sn4—O15—C22−79.97 (11)Sn3—C45—C46—C47174.73 (13)
O12—Sn4—O15—C22−159.18 (18)C45—C46—C47—C48−69.0 (2)
Sn1—O4—C1—O3−38.2 (3)C49X—Sn3—C49—C50−22 (2)
Sn1—O4—C1—C2141.23 (14)O1—Sn3—C49—C50−179.25 (16)
Sn3—O3—C1—O4−22.1 (3)C45—Sn3—C49—C50−9.4 (3)
Sn3—O3—C1—C2158.50 (12)O7—Sn3—C49—C5099.38 (17)
O4—C1—C2—C3−4.8 (3)O3—Sn3—C49—C50−88.50 (17)
O3—C1—C2—C3174.61 (17)Sn3—C49—C50—C5167.5 (2)
O4—C1—C2—C7177.97 (17)C49—C50—C51—C5264.9 (3)
O3—C1—C2—C7−2.6 (3)O1—Sn3—C49X—C50X−161.1 (9)
C7—C2—C3—C40.4 (3)C45—Sn3—C49X—C50X3.6 (14)
C1—C2—C3—C4−176.93 (17)C49—Sn3—C49X—C50X174 (3)
C2—C3—C4—C5−0.3 (3)O7—Sn3—C49X—C50X112.8 (11)
C2—C3—C4—N1176.96 (16)O3—Sn3—C49X—C50X−73.0 (11)
O5—N1—C4—C3−169.13 (18)Sn3—C49X—C50X—C51X166.1 (12)
O6—N1—C4—C310.1 (3)C49X—C50X—C51X—C52X−70 (2)
O5—N1—C4—C58.2 (3)O2—Sn4—C53—C54171.92 (13)
O6—N1—C4—C5−172.65 (18)C57—Sn4—C53—C5411.1 (2)
C3—C4—C5—C6−0.9 (3)O15—Sn4—C53—C54−105.84 (14)
N1—C4—C5—C6−178.09 (17)O12—Sn4—C53—C5482.96 (14)
C4—C5—C6—C71.9 (3)Sn4—C53—C54—C55−60.8 (2)
C5—C6—C7—N2177.84 (18)C53—C54—C55—C56−174.58 (18)
C5—C6—C7—C2−1.8 (3)O2—Sn4—C57—C5899.39 (14)
C3—C2—C7—N2−178.98 (17)C53—Sn4—C57—C58−100.64 (17)
C1—C2—C7—N2−1.8 (3)O15—Sn4—C57—C5816.56 (15)
C3—C2—C7—C60.6 (3)O12—Sn4—C57—C58−176.11 (15)
C1—C2—C7—C6177.74 (17)Sn4—C57—C58—C59−178.80 (14)
Sn3—O7—C8—O81.2 (2)C57—C58—C59—C60−178.49 (18)
D—H···AD—HH···AD···AD—H···A
N2—H1N2···O9i0.86 (3)2.32 (3)3.122 (3)157 (3)
N2—H2N2···O30.84 (3)2.02 (3)2.684 (3)135 (2)
N4—H1N4···O6ii0.84 (3)2.20 (3)3.002 (2)160 (3)
N4—H2N4···O80.87 (3)2.02 (3)2.675 (2)131 (3)
N6—H1N6···O120.82 (3)2.07 (3)2.688 (3)132 (2)
N6—H2N6···O17iii0.83 (3)2.36 (3)3.152 (3)158 (2)
N6—H2N6···O18iii0.83 (3)2.49 (2)3.229 (3)149 (2)
N8—H1N8···O160.86 (3)2.03 (3)2.674 (2)131 (3)
N8—H2N8···O13iv0.82 (3)2.22 (3)2.998 (2)160 (3)
C6—H6A···O9i0.952.483.261 (2)139
C13—H13A···O6ii0.952.573.350 (2)140
C20—H20A···O17iii0.952.543.338 (3)142
C43—H43B···O13v0.992.583.544 (3)164
C50—H50B···O80.992.563.304 (3)131
C54—H54A···O160.992.513.210 (3)128
C58—H58A···O160.992.583.221 (2)123
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
N2—H1N2⋯O9i0.86 (3)2.32 (3)3.122 (3)157 (3)
N2—H2N2⋯O30.84 (3)2.02 (3)2.684 (3)135 (2)
N4—H1N4⋯O6ii0.84 (3)2.20 (3)3.002 (2)160 (3)
N4—H2N4⋯O80.87 (3)2.02 (3)2.675 (2)131 (3)
N6—H1N6⋯O120.82 (3)2.07 (3)2.688 (3)132 (2)
N6—H2N6⋯O17iii0.83 (3)2.36 (3)3.152 (3)158 (2)
N6—H2N6⋯O18iii0.83 (3)2.49 (2)3.229 (3)149 (2)
N8—H1N8⋯O160.86 (3)2.03 (3)2.674 (2)131 (3)
N8—H2N8⋯O13iv0.82 (3)2.22 (3)2.998 (2)160 (3)
C6—H6A⋯O9i0.952.483.261 (2)139
C13—H13A⋯O6ii0.952.573.350 (2)140
C20—H20A⋯O17iii0.952.543.338 (3)142
C43—H43B⋯O13v0.992.583.544 (3)164
C50—H50B⋯O80.992.563.304 (3)131
C54—H54A⋯O160.992.513.210 (3)128
C58—H58A⋯O160.992.583.221 (2)123

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

  6 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Octa-butyl-bis-(μ(2)-2-chloro-5-nitro-benzoato)bis-(2-chloro-5-nitro-benzoato)di-μ(3)-oxido-tetra-tin(IV).

Authors:  Yip-Foo Win; Chen-Shang Choong; Sie-Tiong Ha; Jia Hao Goh; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-30

3.  Octa-n-butyl-1κC,2κC,3κ,4κC-bis-(μ-2,3-dibromo-propionato)-1:2κO:O',3:4κO:O'-bis-(2,3-dibromo-propionato)-1κO,3κO-di-μ(3)-oxido-1:2:4κO:O:O,2:3:4κO:O:O-tetra-tin(IV).

Authors:  Yip Foo Win; Siang Guan Teoh; Sie Tiong Ha; Reza Kia; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-11-20

4.  Bis(μ(2)-4-amino-3-nitro-benzoato)bis-(4-amino-3-nitro-benzoato)octa-butyldi-μ(3)-oxido-tetra-tin(IV).

Authors:  Yip-Foo Win; Chen-Shang Choong; Siang-Guan Teoh; Jia Hao Goh; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-10-13

5.  Octa-butylbis[μ(2)-4-(diethyl-amino)-benzoato-κO:O']bis-[4-(diethyl-amino)-benzoato-κO]di-μ(3)-oxido-tetra-tin(IV).

Authors:  Yip-Foo Win; Chen-Shang Choong; Sie-Tiong Ha; Chin Sing Yeap; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-07-02

6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  6 in total
  1 in total

1.  2-Amino-3-nitro-benzoic acid.

Authors:  Yip-Foo Win; Chen-Shang Choong; Siang-Guan Teoh; Ching Kheng Quah; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-01-21
  1 in total

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