Literature DB >> 21589351

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

Yip-Foo Win, Chen-Shang Choong, Sie-Tiong Ha, Jia Hao Goh, Hoong-Kun Fun.   

Abstract

The title complex, [Sn(4)(C(4)H(9))(8)(C(7)H(3)n class="Chemical">ClNO(4))(4)O(2)], is a cluster formed by a crystallographic inversion center around the central Sn(2)O(2) ring. Both of the two independent Sn atoms are five-coordinated, with distorted trigonal-bipyramidal SnC(2)O(3) geometries. One Sn atom is coordinated by two butyl groups, one O atom of the benzoate anion and two bridging O atoms, whereas the other Sn atom is coordinated by two butyl groups, two O atoms of the benzoate anions and a bridging O atom. The O atoms of the bridging benzoate anion are disordered over two sites with an occupancy ratio of 0.862 (12):0.138 (12). One of the butyl groups coordinated to the Sn(2)O(2) ring is disordered over two sites with an occupancy ratio of 0.780 (8):0.220 (8), whereas both of the two butyl groups coordinated to the other Sn atom are disordered over two sites with occupancy ratios of 0.788 (5):0.212 (5) and 0.827 (10):0.173 (10). All the butyl groups are equatorial with respect to the SnO(3) trigonal plane. In the crystal, complex mol-ecules are stacked down [010] with weak inter-molecular C-H⋯π inter-actions stabilizing the crystal structure.

Entities:  

Year:  2010        PMID: 21589351      PMCID: PMC3011528          DOI: 10.1107/S1600536810049317

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


Related literature

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

Experimental

Crystal data

[Sn4(C4H9)8(C7H3ClNO4)4O2] M = 882.94 Triclinic, a = 13.2278 (14) Å b = 13.2554 (14) Å c = 13.3279 (13) Å α = 61.523 (2)° β = 87.345 (2)° γ = 63.252 (2)° V = 1791.7 (3) Å3 Z = 2 Mo Kα radiation μ = 1.59 mm−1 T = 100 K 0.27 × 0.17 × 0.09 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.673, T max = 0.867 21637 measured reflections 7668 independent reflections 6167 reflections with I > 2σ(I) R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.031 wR(F 2) = 0.078 S = 1.04 7668 reflections 466 parameters 221 restraints H-atom parameters constrained Δρmax = 0.97 e Å−3 Δρmin = −0.88 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAIn class="Chemical">NT (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 datablocks global, I. DOI: 10.1107/S1600536810049317/ng5076sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049317/ng5076Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Sn4(C4H9)8(C7H3ClNO4)4O2]Z = 2
Mr = 882.94F(000) = 884
Triclinic, P1Dx = 1.637 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.2278 (14) ÅCell parameters from 8142 reflections
b = 13.2554 (14) Åθ = 3.0–29.9°
c = 13.3279 (13) ŵ = 1.59 mm1
α = 61.523 (2)°T = 100 K
β = 87.345 (2)°Plate, colourless
γ = 63.252 (2)°0.27 × 0.17 × 0.09 mm
V = 1791.7 (3) Å3
Bruker APEXII DUO CCD area-detector diffractometer7668 independent reflections
Radiation source: fine-focus sealed tube6167 reflections with I > 2σ(I)
graphiteRint = 0.041
φ and ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −15→16
Tmin = 0.673, Tmax = 0.867k = −16→16
21637 measured reflectionsl = −17→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0196P)2 + 2.5482P] where P = (Fo2 + 2Fc2)/3
7668 reflections(Δ/σ)max = 0.001
466 parametersΔρmax = 0.97 e Å3
221 restraintsΔρmin = −0.88 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
Sn10.56558 (2)0.15969 (2)0.249637 (19)0.02618 (7)
Sn20.380257 (19)0.13444 (2)0.475501 (18)0.02152 (7)
Cl11.02684 (11)−0.10588 (11)0.27696 (10)0.0521 (3)
Cl20.08388 (10)0.50609 (10)0.10191 (9)0.0484 (3)
O10.7938 (3)−0.4845 (3)0.3840 (3)0.0674 (10)
O20.9722 (4)−0.6211 (3)0.4016 (3)0.0700 (11)
O30.6949 (2)−0.0451 (2)0.3168 (2)0.0304 (5)
O40.7651 (3)0.0447 (3)0.1638 (2)0.0439 (7)
O50.1796 (3)0.9708 (3)0.0553 (3)0.0538 (8)
O60.3583 (3)0.8132 (3)0.1108 (3)0.0505 (8)
O70.2895 (3)0.3404 (3)0.3116 (3)0.0337 (11)0.862 (12)
O80.4278 (4)0.3625 (3)0.2169 (4)0.0461 (16)0.862 (12)
O7X0.319 (2)0.355 (2)0.3350 (18)0.024 (5)*0.138 (12)
O8X0.3919 (18)0.3494 (17)0.1808 (15)0.021 (5)*0.138 (12)
O90.5135 (2)0.0726 (2)0.39818 (18)0.0228 (5)
N10.8976 (4)−0.5134 (3)0.3783 (3)0.0478 (9)
N20.2552 (4)0.8570 (3)0.0834 (3)0.0394 (8)
C10.8404 (4)−0.2853 (4)0.3168 (3)0.0341 (8)
H1A0.7637−0.26740.31320.041*
C20.9292 (4)−0.4106 (4)0.3482 (3)0.0350 (9)
C31.0435 (4)−0.4424 (4)0.3558 (3)0.0427 (10)
H3A1.1006−0.52680.37610.051*
C41.0722 (4)−0.3467 (4)0.3326 (3)0.0418 (10)
H4A1.1494−0.36650.33810.050*
C50.9857 (4)−0.2208 (4)0.3009 (3)0.0362 (9)
C60.8683 (3)−0.1871 (4)0.2908 (3)0.0311 (8)
C70.7723 (3)−0.0512 (4)0.2519 (3)0.0307 (8)
C80.4617 (6)0.2056 (7)0.1038 (4)0.0455 (15)0.780 (8)
H8A0.38240.26610.09800.055*0.780 (8)
H8B0.48600.25180.03450.055*0.780 (8)
C90.4623 (7)0.0949 (6)0.1016 (6)0.065 (2)0.780 (8)
H9A0.43820.04770.17060.078*0.780 (8)
H9B0.54090.03470.10520.078*0.780 (8)
C100.3820 (7)0.1382 (8)−0.0081 (6)0.073 (2)0.780 (8)
H10A0.40630.1854−0.07680.088*0.780 (8)
H10B0.39220.0602−0.00650.088*0.780 (8)
C110.2557 (8)0.2235 (9)−0.0202 (6)0.077 (3)0.780 (8)
H11A0.21230.2458−0.09020.116*0.780 (8)
H11B0.24400.3024−0.02420.116*0.780 (8)
H11C0.22990.17690.04620.116*0.780 (8)
C8X0.5005 (15)0.138 (2)0.1177 (17)0.034 (4)*0.220 (8)
H8XA0.52700.17650.04710.041*0.220 (8)
H8XB0.53370.04520.14540.041*0.220 (8)
C9X0.3722 (15)0.200 (2)0.088 (2)0.065 (5)*0.220 (8)
H9XA0.34000.29420.05510.078*0.220 (8)
H9XB0.34580.16760.16050.078*0.220 (8)
C10X0.323 (2)0.179 (4)0.005 (3)0.076 (7)*0.220 (8)
H10C0.35710.2011−0.06300.091*0.220 (8)
H10D0.34740.08590.04260.091*0.220 (8)
C11X0.194 (2)0.253 (4)−0.037 (3)0.097 (8)*0.220 (8)
H11D0.17320.2308−0.08890.145*0.220 (8)
H11E0.16740.3460−0.07830.145*0.220 (8)
H11F0.15760.23100.02840.145*0.220 (8)
C120.6759 (16)0.2280 (18)0.2698 (10)0.0438 (16)0.827 (10)
H12A0.65080.26190.32200.053*0.827 (10)
H12B0.75410.15480.30540.053*0.827 (10)
C130.6765 (10)0.3368 (12)0.1525 (10)0.0616 (19)0.827 (10)
H13A0.72650.29570.11230.074*0.827 (10)
H13B0.59870.39220.10440.074*0.827 (10)
C140.7162 (7)0.4228 (7)0.1618 (8)0.077 (2)0.827 (10)
H14A0.79080.36710.21580.092*0.827 (10)
H14B0.72700.47650.08590.092*0.827 (10)
C150.6339 (7)0.5109 (7)0.2022 (6)0.072 (2)0.827 (10)
H15A0.66390.56360.20510.108*0.827 (10)
H15B0.62520.45860.27870.108*0.827 (10)
H15C0.56000.56720.14880.108*0.827 (10)
C12X0.675 (9)0.231 (11)0.260 (6)0.062 (7)*0.173 (10)
H12C0.65880.25670.31840.074*0.173 (10)
H12D0.75510.16110.28500.074*0.173 (10)
C13X0.661 (5)0.347 (7)0.144 (5)0.070 (6)*0.173 (10)
H13C0.66180.32710.08320.084*0.173 (10)
H13D0.58620.42240.12720.084*0.173 (10)
C14X0.754 (4)0.384 (4)0.142 (3)0.076 (6)*0.173 (10)
H14C0.82450.32130.13470.091*0.173 (10)
H14D0.73000.47000.07470.091*0.173 (10)
C15X0.779 (4)0.385 (5)0.250 (3)0.097 (8)*0.173 (10)
H15D0.84440.39900.24860.145*0.173 (10)
H15E0.79660.30180.31810.145*0.173 (10)
H15F0.71270.45390.25320.145*0.173 (10)
C160.2873 (3)0.6362 (3)0.1496 (3)0.0286 (8)
H16A0.36240.60270.18620.034*
C170.2146 (4)0.7687 (4)0.0871 (3)0.0319 (8)
C180.1025 (4)0.8243 (4)0.0280 (3)0.0373 (9)
H18A0.05480.9150−0.01390.045*
C190.0640 (4)0.7415 (4)0.0330 (3)0.0373 (9)
H19A−0.01010.7760−0.00700.045*
C200.1365 (4)0.6060 (3)0.0981 (3)0.0324 (8)
C210.2478 (3)0.5513 (3)0.1580 (3)0.0253 (7)
C220.3273 (3)0.4057 (3)0.2329 (3)0.0267 (7)
C230.2412 (4)0.1154 (6)0.4272 (5)0.0322 (12)0.788 (5)
H23A0.24410.03610.49070.039*0.788 (5)
H23B0.16850.18940.41700.039*0.788 (5)
C240.2430 (5)0.1096 (5)0.3162 (4)0.0374 (12)0.788 (5)
H24A0.31970.04380.32210.045*0.788 (5)
H24B0.22910.19380.25090.045*0.788 (5)
C250.1543 (5)0.0773 (5)0.2904 (5)0.0466 (14)0.788 (5)
H25A0.16830.06280.22510.056*0.788 (5)
H25B0.1639−0.00350.35780.056*0.788 (5)
C260.0325 (6)0.1842 (7)0.2620 (6)0.0638 (19)0.788 (5)
H26A−0.02030.15950.24640.096*0.788 (5)
H26B0.02200.26400.19430.096*0.788 (5)
H26C0.01770.19760.32700.096*0.788 (5)
C23X0.2346 (19)0.155 (3)0.3955 (18)0.045 (6)*0.212 (5)
H23C0.17420.24550.36420.054*0.212 (5)
H23D0.25420.14390.32910.054*0.212 (5)
C24X0.1815 (18)0.070 (2)0.4615 (16)0.052 (5)*0.212 (5)
H24C0.14690.09240.51870.063*0.212 (5)
H24D0.2427−0.02100.50390.063*0.212 (5)
C25X0.0908 (19)0.081 (2)0.3867 (17)0.059 (5)*0.212 (5)
H25C0.03620.17340.33450.071*0.212 (5)
H25D0.12780.04380.33910.071*0.212 (5)
C26X0.026 (3)0.013 (4)0.456 (3)0.097 (10)*0.212 (5)
H26D−0.03060.02380.40410.145*0.212 (5)
H26E0.0789−0.07850.50690.145*0.212 (5)
H26F−0.01260.05130.50210.145*0.212 (5)
C270.4218 (4)0.2140 (4)0.5623 (3)0.0337 (8)
H27A0.35190.29140.55070.040*
H27B0.44610.15020.64540.040*
C280.5164 (4)0.2521 (4)0.5239 (3)0.0358 (9)
H28A0.58220.18040.52160.043*
H28B0.48690.32840.44550.043*
C290.5561 (4)0.2830 (5)0.6057 (4)0.0501 (11)
H29A0.48900.35070.61140.060*
H29B0.58900.20490.68290.060*
C300.6441 (5)0.3286 (6)0.5683 (5)0.0690 (16)
H30A0.66260.34960.62220.104*
H30B0.61290.40520.49140.104*
H30C0.71310.26000.56740.104*
U11U22U33U12U13U23
Sn10.02598 (14)0.01702 (12)0.02233 (11)−0.00603 (10)0.00790 (9)−0.00531 (9)
Sn20.01735 (12)0.01475 (11)0.02208 (11)−0.00367 (9)0.00397 (8)−0.00608 (9)
Cl10.0452 (7)0.0433 (6)0.0618 (7)−0.0249 (5)0.0171 (5)−0.0200 (5)
Cl20.0470 (6)0.0276 (5)0.0531 (6)−0.0130 (5)−0.0125 (5)−0.0114 (4)
O10.059 (3)0.046 (2)0.096 (3)−0.0268 (19)0.006 (2)−0.033 (2)
O20.089 (3)0.0323 (18)0.083 (2)−0.0214 (19)0.030 (2)−0.0339 (18)
O30.0316 (14)0.0201 (12)0.0299 (12)−0.0086 (11)0.0138 (11)−0.0105 (10)
O40.0492 (19)0.0256 (14)0.0357 (14)−0.0124 (13)0.0218 (13)−0.0077 (12)
O50.073 (2)0.0277 (16)0.0622 (19)−0.0247 (17)0.0286 (18)−0.0247 (15)
O60.060 (2)0.0399 (18)0.0489 (17)−0.0293 (17)0.0091 (16)−0.0157 (14)
O70.0254 (18)0.0201 (16)0.0292 (16)−0.0034 (14)0.0057 (14)−0.0015 (13)
O80.031 (2)0.0191 (16)0.058 (2)−0.0043 (15)0.0182 (19)−0.0062 (15)
O90.0209 (12)0.0162 (11)0.0206 (10)−0.0050 (10)0.0066 (9)−0.0060 (9)
N10.059 (3)0.0302 (19)0.049 (2)−0.0149 (19)0.0126 (19)−0.0232 (17)
N20.054 (2)0.0283 (18)0.0324 (16)−0.0211 (18)0.0166 (16)−0.0131 (14)
C10.037 (2)0.0272 (19)0.0284 (17)−0.0098 (17)0.0084 (16)−0.0135 (15)
C20.039 (2)0.0267 (19)0.0314 (18)−0.0096 (18)0.0121 (17)−0.0160 (16)
C30.047 (3)0.027 (2)0.0331 (19)−0.0051 (19)0.0111 (18)−0.0123 (17)
C40.035 (2)0.037 (2)0.036 (2)−0.0111 (19)0.0154 (18)−0.0134 (18)
C50.035 (2)0.030 (2)0.0330 (18)−0.0126 (18)0.0162 (17)−0.0132 (16)
C60.038 (2)0.0242 (18)0.0228 (16)−0.0112 (17)0.0133 (15)−0.0101 (14)
C70.032 (2)0.0252 (18)0.0298 (17)−0.0116 (16)0.0127 (15)−0.0131 (15)
C80.039 (3)0.045 (4)0.029 (2)−0.011 (3)0.002 (2)−0.011 (3)
C90.072 (4)0.045 (3)0.057 (3)−0.015 (3)−0.011 (3)−0.023 (3)
C100.078 (6)0.072 (5)0.063 (4)−0.022 (4)−0.008 (4)−0.041 (4)
C110.080 (6)0.087 (6)0.049 (4)−0.051 (5)−0.015 (4)−0.011 (4)
C120.055 (3)0.046 (3)0.052 (4)−0.038 (3)0.028 (3)−0.030 (3)
C130.092 (5)0.054 (4)0.062 (4)−0.050 (4)0.053 (4)−0.035 (3)
C140.054 (4)0.048 (4)0.104 (5)−0.028 (3)0.024 (4)−0.020 (4)
C150.106 (6)0.052 (4)0.062 (4)−0.045 (4)0.019 (4)−0.025 (3)
C160.0274 (19)0.0237 (18)0.0250 (16)−0.0073 (15)0.0105 (14)−0.0109 (14)
C170.046 (2)0.0230 (18)0.0264 (16)−0.0170 (18)0.0154 (16)−0.0126 (15)
C180.040 (2)0.0186 (18)0.0293 (18)−0.0042 (17)0.0025 (16)−0.0042 (15)
C190.033 (2)0.0222 (18)0.0326 (18)−0.0020 (17)−0.0042 (16)−0.0067 (16)
C200.038 (2)0.0209 (18)0.0273 (17)−0.0082 (16)0.0013 (16)−0.0095 (15)
C210.0245 (18)0.0170 (16)0.0227 (15)−0.0032 (14)0.0071 (13)−0.0087 (13)
C220.0243 (19)0.0186 (16)0.0302 (17)−0.0070 (15)0.0021 (14)−0.0106 (14)
C230.016 (2)0.034 (3)0.034 (3)−0.009 (2)−0.0011 (19)−0.011 (2)
C240.038 (3)0.036 (3)0.037 (2)−0.018 (2)0.002 (2)−0.017 (2)
C250.048 (3)0.040 (3)0.049 (3)−0.018 (3)−0.001 (3)−0.023 (3)
C260.049 (4)0.062 (4)0.079 (4)−0.018 (3)−0.004 (3)−0.042 (4)
C270.043 (2)0.0291 (19)0.0353 (19)−0.0196 (18)0.0137 (17)−0.0191 (16)
C280.034 (2)0.033 (2)0.045 (2)−0.0165 (18)0.0125 (17)−0.0234 (18)
C290.058 (3)0.054 (3)0.056 (3)−0.033 (3)0.014 (2)−0.035 (2)
C300.065 (4)0.073 (4)0.093 (4)−0.045 (3)0.011 (3)−0.049 (3)
Sn1—O92.034 (2)C13—H13A0.9700
Sn1—C12X2.096 (10)C13—H13B0.9700
Sn1—C82.098 (5)C14—C151.497 (10)
Sn1—C122.116 (5)C14—H14A0.9700
Sn1—O32.177 (2)C14—H14B0.9700
Sn1—C8X2.180 (19)C15—H15A0.9600
Sn1—O8X2.289 (19)C15—H15B0.9600
Sn1—O82.299 (3)C15—H15C0.9600
Sn2—O92.044 (2)C12X—C13X1.513 (9)
Sn2—C23X2.088 (10)C12X—H12C0.9700
Sn2—C272.121 (3)C12X—H12D0.9700
Sn2—C232.131 (4)C13X—C14X1.504 (9)
Sn2—O9i2.164 (2)C13X—H13C0.9700
Sn2—O72.296 (3)C13X—H13D0.9700
Sn2—O7X2.35 (2)C14X—C15X1.498 (9)
Cl1—C51.728 (4)C14X—H14C0.9700
Cl2—C201.733 (4)C14X—H14D0.9700
O1—N11.257 (5)C15X—H15D0.9600
O2—N11.202 (5)C15X—H15E0.9600
O3—C71.309 (4)C15X—H15F0.9600
O4—C71.217 (4)C16—C171.364 (5)
O5—N21.246 (5)C16—C211.398 (5)
O6—N21.208 (5)C16—H16A0.9300
O7—C221.255 (5)C17—C181.391 (6)
O8—C221.243 (5)C18—C191.378 (6)
O7X—C221.22 (2)C18—H18A0.9300
O8X—C221.279 (19)C19—C201.393 (5)
O9—Sn2i2.164 (2)C19—H19A0.9300
N1—C21.474 (5)C20—C211.389 (5)
N2—C171.472 (5)C21—C221.503 (5)
C1—C21.393 (5)C23—C241.517 (7)
C1—C61.394 (5)C23—H23A0.9700
C1—H1A0.9300C23—H23B0.9700
C2—C31.369 (6)C24—C251.519 (7)
C3—C41.376 (6)C24—H24A0.9700
C3—H3A0.9300C24—H24B0.9700
C4—C51.388 (6)C25—C261.495 (8)
C4—H4A0.9300C25—H25A0.9700
C5—C61.402 (6)C25—H25B0.9700
C6—C71.496 (5)C26—H26A0.9600
C8—C91.478 (8)C26—H26B0.9600
C8—H8A0.9700C26—H26C0.9600
C8—H8B0.9700C23X—C24X1.502 (9)
C9—C101.546 (8)C23X—H23C0.9700
C9—H9A0.9700C23X—H23D0.9700
C9—H9B0.9700C24X—C25X1.505 (9)
C10—C111.500 (11)C24X—H24C0.9700
C10—H10A0.9700C24X—H24D0.9700
C10—H10B0.9700C25X—C26X1.493 (9)
C11—H11A0.9600C25X—H25C0.9700
C11—H11B0.9600C25X—H25D0.9700
C11—H11C0.9600C26X—C26Xii1.31 (5)
C8X—C9X1.487 (9)C26X—H26D0.9601
C8X—H8XA0.9700C26X—H26E0.9600
C8X—H8XB0.9700C26X—H26F0.9600
C9X—C10X1.512 (9)C27—C281.532 (5)
C9X—H9XA0.9700C27—H27A0.9700
C9X—H9XB0.9700C27—H27B0.9700
C10X—C11X1.499 (9)C28—C291.518 (5)
C10X—H10C0.9700C28—H28A0.9700
C10X—H10D0.9700C28—H28B0.9700
C11X—H11D0.9600C29—C301.504 (7)
C11X—H11E0.9600C29—H29A0.9700
C11X—H11F0.9600C29—H29B0.9700
C12—C131.543 (7)C30—H30A0.9600
C12—H12A0.9700C30—H30B0.9600
C12—H12B0.9700C30—H30C0.9600
C13—C141.507 (9)
O9—Sn1—C12X117 (2)C14—C13—H13B108.4
O9—Sn1—C8110.57 (17)C12—C13—H13B108.4
C12X—Sn1—C8130.4 (18)H13A—C13—H13B107.5
O9—Sn1—C12113.6 (3)C15—C14—C13113.9 (7)
C12X—Sn1—C123(3)C15—C14—H14A108.8
C8—Sn1—C12133.3 (4)C13—C14—H14A108.8
O9—Sn1—O380.20 (9)C15—C14—H14B108.8
C12X—Sn1—O399 (4)C13—C14—H14B108.8
C8—Sn1—O3103.1 (2)H14A—C14—H14B107.7
C12—Sn1—O398.5 (6)C14—C15—H15A109.5
O9—Sn1—C8X107.7 (5)C14—C15—H15B109.5
C12X—Sn1—C8X135 (2)H15A—C15—H15B109.5
C8—Sn1—C8X19.6 (5)C14—C15—H15C109.5
C12—Sn1—C8X138.4 (6)H15A—C15—H15C109.5
O3—Sn1—C8X83.5 (6)H15B—C15—H15C109.5
O9—Sn1—O8X90.3 (4)C13X—C12X—Sn1112 (3)
C12X—Sn1—O8X99 (4)C13X—C12X—H12C109.2
C8—Sn1—O8X66.0 (6)Sn1—C12X—H12C109.2
C12—Sn1—O8X99.1 (8)C13X—C12X—H12D109.2
O3—Sn1—O8X162.1 (6)Sn1—C12X—H12D109.2
C8X—Sn1—O8X85.0 (8)H12C—C12X—H12D107.9
O9—Sn1—O889.69 (10)C14X—C13X—C12X113 (2)
C12X—Sn1—O881 (4)C14X—C13X—H13C108.9
C8—Sn1—O885.2 (3)C12X—C13X—H13C108.9
C12—Sn1—O880.7 (6)C14X—C13X—H13D108.9
O3—Sn1—O8168.65 (13)C12X—C13X—H13D108.9
C8X—Sn1—O8104.7 (6)H13C—C13X—H13D107.7
O8X—Sn1—O820.4 (5)C15X—C14X—C13X113 (2)
O9—Sn2—C23X107.8 (9)C15X—C14X—H14C109.0
O9—Sn2—C27108.23 (13)C13X—C14X—H14C109.0
C23X—Sn2—C27139.5 (10)C15X—C14X—H14D109.0
O9—Sn2—C23109.92 (18)C13X—C14X—H14D109.0
C23X—Sn2—C2312.5 (6)H14C—C14X—H14D107.8
C27—Sn2—C23141.4 (2)C14X—C15X—H15D109.5
O9—Sn2—O9i76.18 (9)C14X—C15X—H15E109.5
C23X—Sn2—O9i106.8 (7)H15D—C15X—H15E109.5
C27—Sn2—O9i99.21 (12)C14X—C15X—H15F109.5
C23—Sn2—O9i95.09 (18)H15D—C15X—H15F109.5
O9—Sn2—O791.26 (10)H15E—C15X—H15F109.5
C23X—Sn2—O772.3 (6)C17—C16—C21119.5 (3)
C27—Sn2—O789.01 (18)C17—C16—H16A120.3
C23—Sn2—O784.7 (2)C21—C16—H16A120.3
O9i—Sn2—O7166.62 (11)C16—C17—C18122.7 (3)
O9—Sn2—O7X91.2 (5)C16—C17—N2119.0 (4)
C23X—Sn2—O7X87.7 (9)C18—C17—N2118.3 (3)
C27—Sn2—O7X73.7 (6)C19—C18—C17118.3 (3)
C23—Sn2—O7X99.9 (7)C19—C18—H18A120.9
O9i—Sn2—O7X163.1 (6)C17—C18—H18A120.9
O7—Sn2—O7X16.1 (5)C18—C19—C20119.7 (4)
C7—O3—Sn1109.3 (2)C18—C19—H19A120.2
C22—O7—Sn2132.3 (3)C20—C19—H19A120.2
C22—O8—Sn1133.2 (3)C21—C20—C19121.7 (3)
C22—O7X—Sn2130.3 (15)C21—C20—Cl2120.4 (3)
C22—O8X—Sn1131.3 (12)C19—C20—Cl2117.9 (3)
Sn1—O9—Sn2135.82 (11)C20—C21—C16118.2 (3)
Sn1—O9—Sn2i120.19 (11)C20—C21—C22123.4 (3)
Sn2—O9—Sn2i103.82 (9)C16—C21—C22118.3 (3)
O2—N1—O1123.7 (4)O7X—C22—O8115.2 (11)
O2—N1—C2119.0 (4)O8—C22—O7125.7 (3)
O1—N1—C2117.2 (4)O7X—C22—O8X128.2 (13)
O6—N2—O5125.0 (4)O7—C22—O8X116.0 (9)
O6—N2—C17118.0 (3)O7X—C22—C21115.8 (10)
O5—N2—C17116.9 (4)O8—C22—C21116.7 (3)
C2—C1—C6118.9 (4)O7—C22—C21117.3 (3)
C2—C1—H1A120.6O8X—C22—C21115.9 (8)
C6—C1—H1A120.6C24—C23—Sn2114.0 (4)
C3—C2—C1123.0 (4)C24—C23—H23A108.7
C3—C2—N1119.3 (4)Sn2—C23—H23A108.7
C1—C2—N1117.8 (4)C24—C23—H23B108.7
C2—C3—C4118.6 (4)Sn2—C23—H23B108.7
C2—C3—H3A120.7H23A—C23—H23B107.6
C4—C3—H3A120.7C23—C24—C25114.2 (4)
C3—C4—C5120.0 (4)C23—C24—H24A108.7
C3—C4—H4A120.0C25—C24—H24A108.7
C5—C4—H4A120.0C23—C24—H24B108.7
C4—C5—C6121.7 (4)C25—C24—H24B108.7
C4—C5—Cl1118.0 (3)H24A—C24—H24B107.6
C6—C5—Cl1120.3 (3)C26—C25—C24112.4 (5)
C1—C6—C5117.9 (4)C26—C25—H25A109.1
C1—C6—C7118.7 (4)C24—C25—H25A109.1
C5—C6—C7123.3 (3)C26—C25—H25B109.1
O4—C7—O3123.3 (4)C24—C25—H25B109.1
O4—C7—C6122.0 (3)H25A—C25—H25B107.9
O3—C7—C6114.7 (3)C25—C26—H26A109.5
C9—C8—Sn1117.2 (4)C25—C26—H26B109.5
C9—C8—H8A108.0H26A—C26—H26B109.5
Sn1—C8—H8A108.0C25—C26—H26C109.5
C9—C8—H8B108.0H26A—C26—H26C109.5
Sn1—C8—H8B108.0H26B—C26—H26C109.5
H8A—C8—H8B107.3C24X—C23X—Sn2121.6 (12)
C8—C9—C10113.5 (5)C24X—C23X—H23C106.9
C8—C9—H9A108.9Sn2—C23X—H23C106.9
C10—C9—H9A108.9C24X—C23X—H23D106.9
C8—C9—H9B108.9Sn2—C23X—H23D106.9
C10—C9—H9B108.9H23C—C23X—H23D106.7
H9A—C9—H9B107.7C23X—C24X—C25X114.7 (13)
C11—C10—C9114.8 (7)C23X—C24X—H24C108.6
C11—C10—H10A108.6C25X—C24X—H24C108.6
C9—C10—H10A108.6C23X—C24X—H24D108.6
C11—C10—H10B108.6C25X—C24X—H24D108.6
C9—C10—H10B108.6H24C—C24X—H24D107.6
H10A—C10—H10B107.5C26X—C25X—C24X113.1 (17)
C10—C11—H11A109.5C26X—C25X—H25C108.9
C10—C11—H11B109.5C24X—C25X—H25C108.9
H11A—C11—H11B109.5C26X—C25X—H25D108.9
C10—C11—H11C109.5C24X—C25X—H25D108.9
H11A—C11—H11C109.5H25C—C25X—H25D107.8
H11B—C11—H11C109.5C26Xii—C26X—C25X149 (4)
C9X—C8X—Sn1114.2 (13)C26Xii—C26X—H26D94.5
C9X—C8X—H8XA108.7C25X—C26X—H26D109.4
Sn1—C8X—H8XA108.7C26Xii—C26X—H26E79.5
C9X—C8X—H8XB108.7C25X—C26X—H26E109.6
Sn1—C8X—H8XB108.7H26D—C26X—H26E109.5
H8XA—C8X—H8XB107.6C25X—C26X—H26F109.4
C8X—C9X—C10X116.5 (17)H26D—C26X—H26F109.5
C8X—C9X—H9XA108.2H26E—C26X—H26F109.5
C10X—C9X—H9XA108.2C28—C27—Sn2116.0 (3)
C8X—C9X—H9XB108.2C28—C27—H27A108.3
C10X—C9X—H9XB108.2Sn2—C27—H27A108.3
H9XA—C9X—H9XB107.3C28—C27—H27B108.3
C11X—C10X—C9X118 (2)Sn2—C27—H27B108.3
C11X—C10X—H10C107.9H27A—C27—H27B107.4
C9X—C10X—H10C107.9C29—C28—C27111.9 (3)
C11X—C10X—H10D107.9C29—C28—H28A109.2
C9X—C10X—H10D107.9C27—C28—H28A109.2
H10C—C10X—H10D107.2C29—C28—H28B109.2
C10X—C11X—H11D109.5C27—C28—H28B109.2
C10X—C11X—H11E109.5H28A—C28—H28B107.9
H11D—C11X—H11E109.5C30—C29—C28114.2 (4)
C10X—C11X—H11F109.5C30—C29—H29A108.7
H11D—C11X—H11F109.5C28—C29—H29A108.7
H11E—C11X—H11F109.5C30—C29—H29B108.7
C13—C12—Sn1112.5 (6)C28—C29—H29B108.7
C13—C12—H12A109.1H29A—C29—H29B107.6
Sn1—C12—H12A109.1C29—C30—H30A109.5
C13—C12—H12B109.1C29—C30—H30B109.5
Sn1—C12—H12B109.1H30A—C30—H30B109.5
H12A—C12—H12B107.8C29—C30—H30C109.5
C14—C13—C12115.4 (8)H30A—C30—H30C109.5
C14—C13—H13A108.4H30B—C30—H30C109.5
C12—C13—H13A108.4
O9—Sn1—O3—C7−173.6 (2)O9—Sn1—C8X—C9X60.4 (17)
C12X—Sn1—O3—C7−58 (2)C12X—Sn1—C8X—C9X−126 (5)
C8—Sn1—O3—C777.4 (3)C8—Sn1—C8X—C9X−41.3 (15)
C12—Sn1—O3—C7−60.9 (4)C12—Sn1—C8X—C9X−126.5 (17)
C8X—Sn1—O3—C777.1 (5)O3—Sn1—C8X—C9X138.0 (17)
O8X—Sn1—O3—C7127.5 (15)O8X—Sn1—C8X—C9X−28.3 (17)
O8—Sn1—O3—C7−146.3 (8)O8—Sn1—C8X—C9X−34.0 (17)
O9—Sn2—O7—C22−28.3 (5)Sn1—C8X—C9X—C10X−175 (2)
C23X—Sn2—O7—C22−136.7 (11)C8X—C9X—C10X—C11X−173 (3)
C27—Sn2—O7—C2279.9 (5)O9—Sn1—C12—C13−157.9 (10)
C23—Sn2—O7—C22−138.2 (6)C8—Sn1—C12—C132.0 (18)
O9i—Sn2—O7—C22−48.3 (11)O3—Sn1—C12—C13119.1 (12)
O7X—Sn2—O7—C2262 (2)C8X—Sn1—C12—C1329 (2)
O9—Sn1—O8—C22−36.9 (6)O8X—Sn1—C12—C13−63.5 (13)
C12X—Sn1—O8—C22−154 (2)O8—Sn1—C12—C13−72.4 (12)
C8—Sn1—O8—C2273.7 (6)Sn1—C12—C13—C14159.1 (10)
C12—Sn1—O8—C22−151.0 (7)C12—C13—C14—C15−68.8 (13)
O3—Sn1—O8—C22−63.8 (12)O9—Sn1—C12X—C13X−151 (6)
C8X—Sn1—O8—C2271.3 (8)C8—Sn1—C12X—C13X10 (11)
O8X—Sn1—O8—C2254.9 (13)O3—Sn1—C12X—C13X126 (8)
O9—Sn2—O7X—C2229 (2)C8X—Sn1—C12X—C13X36 (11)
C23X—Sn2—O7X—C22−79 (2)O8X—Sn1—C12X—C13X−56 (8)
C27—Sn2—O7X—C22138 (2)O8—Sn1—C12X—C13X−66 (8)
C23—Sn2—O7X—C22−81 (2)Sn1—C12X—C13X—C14X−169 (5)
O9i—Sn2—O7X—C2271 (3)C12X—C13X—C14X—C15X−45 (8)
O7—Sn2—O7X—C22−61 (2)C21—C16—C17—C18−1.8 (5)
O9—Sn1—O8X—C2237.7 (19)C21—C16—C17—N2177.2 (3)
C12X—Sn1—O8X—C22−79 (3)O6—N2—C17—C1617.6 (5)
C8—Sn1—O8X—C22150 (2)O5—N2—C17—C16−160.4 (3)
C12—Sn1—O8X—C22−76.3 (19)O6—N2—C17—C18−163.4 (3)
O3—Sn1—O8X—C2295 (3)O5—N2—C17—C1818.7 (5)
C8X—Sn1—O8X—C22145 (2)C16—C17—C18—C190.0 (6)
O8—Sn1—O8X—C22−50.5 (15)N2—C17—C18—C19−179.0 (3)
C12X—Sn1—O9—Sn288 (4)C17—C18—C19—C201.2 (6)
C8—Sn1—O9—Sn2−76.8 (3)C18—C19—C20—C21−0.5 (6)
C12—Sn1—O9—Sn287.8 (7)C18—C19—C20—Cl2179.8 (3)
O3—Sn1—O9—Sn2−177.14 (18)C19—C20—C21—C16−1.3 (5)
C8X—Sn1—O9—Sn2−97.3 (6)Cl2—C20—C21—C16178.3 (3)
O8X—Sn1—O9—Sn2−12.4 (6)C19—C20—C21—C22177.6 (4)
O8—Sn1—O9—Sn28.0 (2)Cl2—C20—C21—C22−2.8 (5)
C12X—Sn1—O9—Sn2i−87 (4)C17—C16—C21—C202.4 (5)
C8—Sn1—O9—Sn2i108.9 (2)C17—C16—C21—C22−176.6 (3)
C12—Sn1—O9—Sn2i−86.6 (7)Sn2—O7X—C22—O8−57 (2)
O3—Sn1—O9—Sn2i8.54 (11)Sn2—O7X—C22—O761.2 (19)
C8X—Sn1—O9—Sn2i88.4 (6)Sn2—O7X—C22—O8X−15 (3)
O8X—Sn1—O9—Sn2i173.3 (6)Sn2—O7X—C22—C21161.8 (13)
O8—Sn1—O9—Sn2i−166.29 (19)Sn1—O8—C22—O7X63.8 (12)
C23X—Sn2—O9—Sn181.5 (7)Sn1—O8—C22—O730.4 (7)
C27—Sn2—O9—Sn1−79.64 (19)Sn1—O8—C22—O8X−56.8 (13)
C23—Sn2—O9—Sn194.6 (2)Sn1—O8—C22—C21−155.4 (4)
O9i—Sn2—O9—Sn1−174.9 (2)Sn2—O7—C22—O7X−67 (2)
O7—Sn2—O9—Sn19.7 (2)Sn2—O7—C22—O811.7 (7)
O7X—Sn2—O9—Sn1−6.4 (7)Sn2—O7—C22—O8X54.4 (10)
C23X—Sn2—O9—Sn2i−103.5 (7)Sn2—O7—C22—C21−162.5 (3)
C27—Sn2—O9—Sn2i95.31 (13)Sn1—O8X—C22—O7X−27 (2)
C23—Sn2—O9—Sn2i−90.46 (19)Sn1—O8X—C22—O854.7 (14)
O9i—Sn2—O9—Sn2i0.0Sn1—O8X—C22—O7−61 (2)
O7—Sn2—O9—Sn2i−175.32 (17)Sn1—O8X—C22—C21155.6 (12)
O7X—Sn2—O9—Sn2i168.6 (6)C20—C21—C22—O7X−88.0 (15)
C6—C1—C2—C30.5 (6)C16—C21—C22—O7X91.0 (14)
C6—C1—C2—N1178.4 (3)C20—C21—C22—O8131.5 (5)
O2—N1—C2—C3−4.7 (6)C16—C21—C22—O8−49.6 (5)
O1—N1—C2—C3171.6 (4)C20—C21—C22—O7−53.8 (6)
O2—N1—C2—C1177.4 (4)C16—C21—C22—O7125.2 (4)
O1—N1—C2—C1−6.4 (5)C20—C21—C22—O8X89.3 (13)
C1—C2—C3—C40.8 (6)C16—C21—C22—O8X−91.7 (13)
N1—C2—C3—C4−177.1 (3)O9—Sn2—C23—C24−21.1 (5)
C2—C3—C4—C5−0.8 (6)C23X—Sn2—C23—C2461 (5)
C3—C4—C5—C6−0.4 (6)C27—Sn2—C23—C24150.1 (3)
C3—C4—C5—Cl1178.1 (3)O9i—Sn2—C23—C24−98.2 (4)
C2—C1—C6—C5−1.7 (5)O7—Sn2—C23—C2468.4 (4)
C2—C1—C6—C7177.3 (3)O7X—Sn2—C23—C2473.9 (7)
C4—C5—C6—C11.7 (5)Sn2—C23—C24—C25172.0 (4)
Cl1—C5—C6—C1−176.8 (3)C23—C24—C25—C2667.0 (7)
C4—C5—C6—C7−177.2 (3)O9—Sn2—C23X—C24X115 (2)
Cl1—C5—C6—C74.3 (5)C27—Sn2—C23X—C24X−93 (2)
Sn1—O3—C7—O4−4.5 (4)C23—Sn2—C23X—C24X13 (3)
Sn1—O3—C7—C6178.4 (2)O9i—Sn2—C23X—C24X34 (3)
C1—C6—C7—O4−128.9 (4)O7—Sn2—C23X—C24X−160 (3)
C5—C6—C7—O450.0 (5)O7X—Sn2—C23X—C24X−155 (3)
C1—C6—C7—O348.2 (5)Sn2—C23X—C24X—C25X−169.8 (19)
C5—C6—C7—O3−132.9 (4)C23X—C24X—C25X—C26X−170 (3)
O9—Sn1—C8—C9−61.4 (6)C24X—C25X—C26X—C26Xii42 (10)
C12X—Sn1—C8—C9137 (5)O9—Sn2—C27—C2818.4 (3)
C12—Sn1—C8—C9138.2 (10)C23X—Sn2—C27—C28−133.4 (9)
O3—Sn1—C8—C922.8 (6)C23—Sn2—C27—C28−152.9 (3)
C8X—Sn1—C8—C923.6 (16)O9i—Sn2—C27—C2896.7 (3)
O8X—Sn1—C8—C9−142.2 (8)O7—Sn2—C27—C28−72.6 (3)
O8—Sn1—C8—C9−149.3 (5)O7X—Sn2—C27—C28−67.5 (6)
Sn1—C8—C9—C10179.2 (6)Sn2—C27—C28—C29−169.1 (3)
C8—C9—C10—C11−63.2 (10)C27—C28—C29—C30−176.7 (4)
Cg1 is the centroid of the C16–C21 ring.
D—H···AD—HH···AD···AD—H···A
C13—H13A···Cg1iii0.972.923.800 (14)151
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 ring.

D—H⋯AD—HH⋯ADAD—H⋯A
C13—H13ACg1i0.972.923.800 (14)151

Symmetry code: (i) .

  4 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-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

3.  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

4.  Structure validation in chemical crystallography.

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

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

Authors:  Yip-Foo Win; Chen-Shang Choong; Siang-Guan Teoh; Chin Sing Yeap; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-07-23

2.  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
  2 in total

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