Literature DB >> 21754275

(2-Chloro-4-nitro-benzoato)(methanol)triphenyl-tin(IV).

Yip-Foo Win, Chen-Shang Choong, Sie-Tiong Ha, Ching Kheng Quah, Hoong-Kun Fun.   

Abstract

In the title complex, [Sn(C(6)H(5))(3)(C(7)H(3)ClNO(4))(CH(4)O)], the five-coordinate Sn(IV) atom exists in a trigonal-bipyramidal environment, formed by a monodentate carboxyl-ate group, three phenyl rings and a methanol mol-ecule. The axial sites are occupied by the O atoms of the methanol mol-ecule and the carboxyl-ate group, while the equatorial plane is formed by the C atoms of three phenyl rings. The benzene ring of the 2-chloro-4-nitro-benzoate ligand makes dihedral angles of 66.18 (7), 74.71 (7) and 77.39 (7)° with respect to the three phenyl rings. In the crystal, the mol-ecules are linked via inter-molecular O-H⋯O and C-H⋯O hydrogen bonds into a column along the b axis.

Entities:  

Year:  2011        PMID: 21754275      PMCID: PMC3089065          DOI: 10.1107/S1600536811011962

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


Related literature

For general background to and the coordination environment of the title complex, see: Yeap & Teoh (2003 ▶); Szorcsik et al. (2006 ▶); Álvarez-Boo et al. (2006 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Sn(C6H5)3(C7H3ClNO4)(CH4O)] M = 582.59 Monoclinic, a = 9.0287 (3) Å b = 13.5239 (4) Å c = 20.7505 (6) Å β = 108.894 (1)° V = 2397.19 (13) Å3 Z = 4 Mo Kα radiation μ = 1.22 mm−1 T = 100 K 0.27 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.739, T max = 0.835 42634 measured reflections 10460 independent reflections 9263 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.024 wR(F 2) = 0.060 S = 1.04 10460 reflections 312 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 2.82 e Å−3 Δρmin = −1.27 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 datablocks global, I. DOI: 10.1107/S1600536811011962/is2695sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011962/is2695Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Sn(C6H5)3(C7H3ClNO4)(CH4O)]F(000) = 1168
Mr = 582.59Dx = 1.614 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9909 reflections
a = 9.0287 (3) Åθ = 3.7–37.5°
b = 13.5239 (4) ŵ = 1.22 mm1
c = 20.7505 (6) ÅT = 100 K
β = 108.894 (1)°Block, yellow
V = 2397.19 (13) Å30.27 × 0.25 × 0.15 mm
Z = 4
Bruker SMART APEXII DUO CCD area-detector diffractometer10460 independent reflections
Radiation source: fine-focus sealed tube9263 reflections with I > 2σ(I)
graphiteRint = 0.023
φ and ω scansθmax = 35.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −14→13
Tmin = 0.739, Tmax = 0.835k = −21→21
42634 measured reflectionsl = −33→33
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.023P)2 + 1.8694P] where P = (Fo2 + 2Fc2)/3
10460 reflections(Δ/σ)max = 0.002
312 parametersΔρmax = 2.82 e Å3
0 restraintsΔρmin = −1.27 e Å3
Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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*/Ueq
Sn10.122653 (9)0.424304 (6)0.818254 (4)0.01437 (2)
Cl10.40606 (4)0.15616 (2)0.956246 (16)0.02241 (6)
O10.29055 (11)0.30392 (7)0.83558 (5)0.01747 (16)
O20.11079 (11)0.20667 (7)0.76526 (5)0.01919 (17)
O3−0.03497 (11)0.56098 (7)0.82164 (5)0.01848 (16)
O40.73247 (14)−0.13409 (9)0.91070 (7)0.0300 (2)
O50.65369 (15)−0.16195 (9)0.80196 (7)0.0315 (2)
N10.65602 (14)−0.11287 (9)0.85191 (7)0.0221 (2)
C1−0.01601 (14)0.35355 (9)0.86993 (6)0.01578 (19)
C20.05009 (15)0.30813 (10)0.93321 (6)0.0186 (2)
H2A0.15830.30750.95350.022*
C3−0.04454 (18)0.26366 (11)0.96633 (7)0.0228 (2)
H3A0.00060.23451.00880.027*
C4−0.20606 (18)0.26288 (11)0.93602 (8)0.0256 (3)
H4A−0.26910.23310.95810.031*
C5−0.27347 (17)0.30654 (12)0.87268 (8)0.0262 (3)
H5A−0.38150.30530.85210.031*
C6−0.17904 (15)0.35222 (11)0.84008 (7)0.0220 (2)
H6A−0.22480.38220.79800.026*
C70.02070 (15)0.43698 (9)0.71033 (6)0.0180 (2)
C8−0.09430 (16)0.37151 (10)0.67264 (7)0.0212 (2)
H8A−0.12500.31960.69490.025*
C9−0.16407 (19)0.38189 (13)0.60273 (7)0.0279 (3)
H9A−0.24130.33790.57860.033*
C10−0.1169 (2)0.45913 (14)0.56922 (8)0.0311 (3)
H10A−0.16080.46600.52230.037*
C11−0.0041 (2)0.52566 (12)0.60623 (8)0.0294 (3)
H11A0.02610.57770.58400.035*
C120.06386 (17)0.51509 (10)0.67604 (7)0.0229 (2)
H12A0.13880.56030.70030.027*
C130.31789 (14)0.51920 (9)0.86282 (7)0.0173 (2)
C140.30934 (16)0.61928 (10)0.84459 (8)0.0217 (2)
H14A0.21590.64490.81560.026*
C150.43893 (17)0.68101 (11)0.86929 (8)0.0252 (3)
H15A0.43160.74720.85660.030*
C160.57927 (17)0.64392 (11)0.91288 (8)0.0250 (3)
H16A0.66590.68500.92930.030*
C170.58899 (17)0.54502 (12)0.93165 (8)0.0249 (3)
H17A0.68240.51990.96100.030*
C180.45934 (15)0.48302 (10)0.90679 (7)0.0206 (2)
H18A0.46730.41690.91970.025*
C190.24398 (14)0.22178 (9)0.80545 (6)0.01492 (18)
C200.36213 (13)0.13888 (9)0.82013 (6)0.01443 (18)
C210.39401 (15)0.09388 (10)0.76536 (6)0.0179 (2)
H21A0.34830.11910.72170.021*
C220.49241 (15)0.01247 (10)0.77476 (7)0.0191 (2)
H22A0.5136−0.01700.73820.023*
C230.55811 (14)−0.02348 (9)0.84060 (7)0.0172 (2)
C240.53294 (15)0.02005 (9)0.89647 (7)0.0176 (2)
H24A0.5799−0.00500.94010.021*
C250.43558 (14)0.10218 (9)0.88556 (6)0.01563 (19)
C26−0.02762 (18)0.60801 (11)0.88443 (7)0.0240 (2)
H26A−0.08950.66720.87500.036*
H26B0.07910.62440.90920.036*
H26D−0.06750.56390.91110.036*
H1O3−0.061 (3)0.600 (2)0.7921 (13)0.042 (7)*
U11U22U33U12U13U23
Sn10.01494 (4)0.01250 (4)0.01648 (4)−0.00049 (2)0.00621 (3)0.00090 (3)
Cl10.03009 (15)0.02303 (13)0.01545 (12)0.00816 (11)0.00921 (10)0.00142 (10)
O10.0181 (4)0.0137 (4)0.0201 (4)0.0010 (3)0.0055 (3)−0.0007 (3)
O20.0163 (4)0.0168 (4)0.0221 (4)0.0006 (3)0.0028 (3)0.0003 (3)
O30.0205 (4)0.0156 (4)0.0193 (4)0.0028 (3)0.0063 (3)−0.0005 (3)
O40.0276 (5)0.0227 (5)0.0402 (6)0.0081 (4)0.0116 (5)0.0084 (4)
O50.0357 (6)0.0223 (5)0.0446 (7)0.0030 (4)0.0243 (5)−0.0055 (5)
N10.0202 (5)0.0152 (4)0.0354 (6)0.0010 (4)0.0152 (4)0.0017 (4)
C10.0150 (4)0.0148 (5)0.0181 (5)−0.0006 (4)0.0063 (4)0.0003 (4)
C20.0192 (5)0.0196 (5)0.0173 (5)0.0004 (4)0.0062 (4)0.0006 (4)
C30.0295 (6)0.0213 (6)0.0208 (5)0.0000 (5)0.0124 (5)0.0021 (4)
C40.0281 (6)0.0227 (6)0.0327 (7)−0.0043 (5)0.0191 (6)0.0002 (5)
C50.0179 (5)0.0258 (6)0.0369 (7)−0.0027 (5)0.0117 (5)0.0017 (6)
C60.0164 (5)0.0232 (6)0.0254 (6)−0.0007 (4)0.0051 (4)0.0045 (5)
C70.0198 (5)0.0161 (5)0.0184 (5)0.0027 (4)0.0068 (4)0.0011 (4)
C80.0223 (5)0.0190 (5)0.0198 (5)−0.0003 (4)0.0030 (4)0.0000 (4)
C90.0295 (7)0.0317 (7)0.0188 (6)0.0060 (6)0.0028 (5)−0.0015 (5)
C100.0347 (8)0.0397 (8)0.0186 (6)0.0145 (7)0.0080 (5)0.0054 (6)
C110.0379 (8)0.0268 (7)0.0282 (7)0.0095 (6)0.0173 (6)0.0111 (5)
C120.0274 (6)0.0193 (5)0.0246 (6)0.0022 (5)0.0121 (5)0.0034 (5)
C130.0170 (5)0.0158 (5)0.0211 (5)−0.0021 (4)0.0088 (4)−0.0014 (4)
C140.0191 (5)0.0151 (5)0.0325 (7)−0.0016 (4)0.0104 (5)−0.0015 (5)
C150.0243 (6)0.0172 (5)0.0371 (7)−0.0055 (5)0.0140 (5)−0.0038 (5)
C160.0229 (6)0.0256 (6)0.0282 (6)−0.0084 (5)0.0108 (5)−0.0061 (5)
C170.0201 (6)0.0289 (7)0.0240 (6)−0.0043 (5)0.0049 (5)−0.0013 (5)
C180.0199 (5)0.0206 (5)0.0215 (5)−0.0023 (4)0.0070 (4)0.0002 (4)
C190.0160 (4)0.0140 (4)0.0156 (4)0.0007 (4)0.0062 (4)0.0025 (4)
C200.0142 (4)0.0138 (4)0.0159 (4)−0.0004 (4)0.0057 (4)0.0007 (4)
C210.0168 (5)0.0217 (5)0.0156 (5)0.0012 (4)0.0058 (4)−0.0006 (4)
C220.0178 (5)0.0212 (5)0.0205 (5)0.0002 (4)0.0094 (4)−0.0033 (4)
C230.0162 (5)0.0133 (4)0.0244 (5)0.0009 (4)0.0096 (4)0.0006 (4)
C240.0189 (5)0.0156 (5)0.0193 (5)0.0026 (4)0.0077 (4)0.0033 (4)
C250.0176 (5)0.0147 (4)0.0155 (5)0.0012 (4)0.0067 (4)0.0006 (4)
C260.0268 (6)0.0243 (6)0.0232 (6)0.0026 (5)0.0112 (5)−0.0036 (5)
Sn1—C12.1218 (12)C10—C111.389 (3)
Sn1—C132.1339 (12)C10—H10A0.9300
Sn1—C72.1346 (13)C11—C121.386 (2)
Sn1—O12.1737 (9)C11—H11A0.9300
Sn1—O32.3477 (9)C12—H12A0.9300
Cl1—C251.7344 (12)C13—C181.3958 (18)
O1—C191.2772 (15)C13—C141.4008 (18)
O2—C191.2385 (15)C14—C151.3929 (19)
O3—C261.4320 (17)C14—H14A0.9300
O3—H1O30.78 (3)C15—C161.390 (2)
O4—N11.2256 (18)C15—H15A0.9300
O5—N11.2252 (17)C16—C171.388 (2)
N1—C231.4709 (17)C16—H16A0.9300
C1—C21.3965 (17)C17—C181.3959 (19)
C1—C61.4001 (17)C17—H17A0.9300
C2—C31.3944 (19)C18—H18A0.9300
C2—H2A0.9300C19—C201.5091 (16)
C3—C41.389 (2)C20—C251.3951 (16)
C3—H3A0.9300C20—C211.3989 (17)
C4—C51.389 (2)C21—C221.3883 (18)
C4—H4A0.9300C21—H21A0.9300
C5—C61.393 (2)C22—C231.3892 (19)
C5—H5A0.9300C22—H22A0.9300
C6—H6A0.9300C23—C241.3831 (18)
C7—C81.3957 (18)C24—C251.3888 (17)
C7—C121.3978 (19)C24—H24A0.9300
C8—C91.3889 (19)C26—H26A0.9600
C8—H8A0.9300C26—H26B0.9600
C9—C101.396 (3)C26—H26D0.9600
C9—H9A0.9300
C1—Sn1—C13126.30 (5)C10—C11—H11A119.7
C1—Sn1—C7116.22 (5)C11—C12—C7120.54 (14)
C13—Sn1—C7114.92 (5)C11—C12—H12A119.7
C1—Sn1—O194.17 (4)C7—C12—H12A119.7
C13—Sn1—O186.84 (4)C18—C13—C14118.29 (12)
C7—Sn1—O1105.92 (4)C18—C13—Sn1121.67 (9)
C1—Sn1—O382.95 (4)C14—C13—Sn1119.91 (9)
C13—Sn1—O386.40 (4)C15—C14—C13120.90 (13)
C7—Sn1—O384.75 (4)C15—C14—H14A119.6
O1—Sn1—O3169.05 (3)C13—C14—H14A119.6
C19—O1—Sn1117.97 (8)C16—C15—C14120.21 (14)
C26—O3—Sn1121.80 (8)C16—C15—H15A119.9
C26—O3—H1O3109.1 (19)C14—C15—H15A119.9
Sn1—O3—H1O3122.4 (19)C17—C16—C15119.46 (13)
O5—N1—O4124.42 (13)C17—C16—H16A120.3
O5—N1—C23117.74 (12)C15—C16—H16A120.3
O4—N1—C23117.83 (12)C16—C17—C18120.39 (14)
C2—C1—C6118.57 (12)C16—C17—H17A119.8
C2—C1—Sn1122.08 (9)C18—C17—H17A119.8
C6—C1—Sn1119.35 (9)C13—C18—C17120.76 (13)
C3—C2—C1120.64 (12)C13—C18—H18A119.6
C3—C2—H2A119.7C17—C18—H18A119.6
C1—C2—H2A119.7O2—C19—O1124.55 (11)
C4—C3—C2120.09 (13)O2—C19—C20118.82 (11)
C4—C3—H3A120.0O1—C19—C20116.63 (10)
C2—C3—H3A120.0C25—C20—C21118.55 (11)
C3—C4—C5119.97 (13)C25—C20—C19122.89 (10)
C3—C4—H4A120.0C21—C20—C19118.50 (10)
C5—C4—H4A120.0C22—C21—C20121.44 (11)
C4—C5—C6119.91 (13)C22—C21—H21A119.3
C4—C5—H5A120.0C20—C21—H21A119.3
C6—C5—H5A120.0C21—C22—C23117.76 (11)
C5—C6—C1120.81 (13)C21—C22—H22A121.1
C5—C6—H6A119.6C23—C22—H22A121.1
C1—C6—H6A119.6C24—C23—C22122.79 (11)
C8—C7—C12118.27 (12)C24—C23—N1118.00 (12)
C8—C7—Sn1121.79 (10)C22—C23—N1119.19 (12)
C12—C7—Sn1119.88 (10)C23—C24—C25118.10 (11)
C9—C8—C7121.64 (14)C23—C24—H24A120.9
C9—C8—H8A119.2C25—C24—H24A120.9
C7—C8—H8A119.2C24—C25—C20121.29 (11)
C8—C9—C10119.19 (15)C24—C25—Cl1117.47 (9)
C8—C9—H9A120.4C20—C25—Cl1121.23 (9)
C10—C9—H9A120.4O3—C26—H26A109.5
C11—C10—C9119.78 (14)O3—C26—H26B109.5
C11—C10—H10A120.1H26A—C26—H26B109.5
C9—C10—H10A120.1O3—C26—H26D109.5
C12—C11—C10120.55 (14)H26A—C26—H26D109.5
C12—C11—H11A119.7H26B—C26—H26D109.5
C1—Sn1—O1—C1967.75 (9)C1—Sn1—C13—C1870.01 (12)
C13—Sn1—O1—C19−166.06 (9)C7—Sn1—C13—C18−128.94 (11)
C7—Sn1—O1—C19−51.03 (10)O1—Sn1—C13—C18−22.84 (11)
O3—Sn1—O1—C19142.03 (17)O3—Sn1—C13—C18148.55 (11)
C1—Sn1—O3—C2666.69 (10)C1—Sn1—C13—C14−114.27 (11)
C13—Sn1—O3—C26−60.57 (10)C7—Sn1—C13—C1446.78 (12)
C7—Sn1—O3—C26−176.03 (10)O1—Sn1—C13—C14152.88 (11)
O1—Sn1—O3—C26−8.6 (2)O3—Sn1—C13—C14−35.73 (10)
C13—Sn1—C1—C2−43.07 (12)C18—C13—C14—C150.4 (2)
C7—Sn1—C1—C2156.10 (10)Sn1—C13—C14—C15−175.42 (11)
O1—Sn1—C1—C246.07 (11)C13—C14—C15—C16−0.2 (2)
O3—Sn1—C1—C2−123.32 (11)C14—C15—C16—C17−0.1 (2)
C13—Sn1—C1—C6136.78 (10)C15—C16—C17—C180.3 (2)
C7—Sn1—C1—C6−24.06 (12)C14—C13—C18—C17−0.3 (2)
O1—Sn1—C1—C6−134.09 (10)Sn1—C13—C18—C17175.52 (11)
O3—Sn1—C1—C656.53 (10)C16—C17—C18—C13−0.1 (2)
C6—C1—C2—C3−0.89 (19)Sn1—O1—C19—O22.35 (16)
Sn1—C1—C2—C3178.95 (10)Sn1—O1—C19—C20−178.31 (7)
C1—C2—C3—C41.0 (2)O2—C19—C20—C25−121.72 (13)
C2—C3—C4—C5−0.1 (2)O1—C19—C20—C2558.90 (16)
C3—C4—C5—C6−0.9 (2)O2—C19—C20—C2155.28 (16)
C4—C5—C6—C10.9 (2)O1—C19—C20—C21−124.10 (12)
C2—C1—C6—C5−0.1 (2)C25—C20—C21—C222.03 (19)
Sn1—C1—C6—C5−179.91 (11)C19—C20—C21—C22−175.10 (11)
C1—Sn1—C7—C8−25.33 (12)C20—C21—C22—C230.30 (19)
C13—Sn1—C7—C8171.64 (10)C21—C22—C23—C24−1.91 (19)
O1—Sn1—C7—C877.66 (11)C21—C22—C23—N1176.70 (11)
O3—Sn1—C7—C8−104.81 (11)O5—N1—C23—C24166.13 (12)
C1—Sn1—C7—C12151.78 (10)O4—N1—C23—C24−12.73 (18)
C13—Sn1—C7—C12−11.26 (12)O5—N1—C23—C22−12.54 (18)
O1—Sn1—C7—C12−105.24 (10)O4—N1—C23—C22168.60 (12)
O3—Sn1—C7—C1272.30 (11)C22—C23—C24—C251.09 (19)
C12—C7—C8—C90.7 (2)N1—C23—C24—C25−177.53 (11)
Sn1—C7—C8—C9177.85 (11)C23—C24—C25—C201.37 (19)
C7—C8—C9—C100.7 (2)C23—C24—C25—Cl1−179.71 (10)
C8—C9—C10—C11−1.5 (2)C21—C20—C25—C24−2.89 (18)
C9—C10—C11—C121.0 (2)C19—C20—C25—C24174.11 (11)
C10—C11—C12—C70.4 (2)C21—C20—C25—Cl1178.24 (9)
C8—C7—C12—C11−1.2 (2)C19—C20—C25—Cl1−4.76 (17)
Sn1—C7—C12—C11−178.43 (11)
D—H···AD—HH···AD···AD—H···A
O3—H1O3···O2i0.79 (3)1.83 (3)2.6082 (14)170 (3)
C16—H16A···O4ii0.932.583.312 (2)136
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
O3—H1O3⋯O2i0.79 (3)1.83 (3)2.6082 (14)170 (3)
C16—H16A⋯O4ii0.932.583.312 (2)136

Symmetry codes: (i) ; (ii) .

  2 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.  Structure validation in chemical crystallography.

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

1.  catena-Poly[[triphenyl-tin(IV)]-μ-5-amino-2-nitro-benzoato-κO:O].

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:  2011-08-27

2.  (4-Chloro-3-nitro-benzoato)triphenyl-tin(IV).

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:  2011-08-27
  2 in total

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