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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): m965.
Published online 2010 July 17. doi:  10.1107/S1600536810027790
PMCID: PMC3007514

Chloridometh­yl(2-methyl­quinolin-8-olato-κ2 N,O)phenyl­tin(IV)

Abstract

The asymmetric unit of the title complex, [Sn(CH3)(C6H5)(C10H8NO)Cl], consists of two independent mol­ecules, both of which have the N,O-chelated SnIV atom in a cis-C2SnNOCl trigonal-bipyramidal geometry [C—Sn—C = 124.82 (8) and 137.69 (8)°]. The Cl atom of the mol­ecule with the smaller C—Sn—C angle inter­acts weakly with the SnIV atom of the mol­ecule with the wider C—Sn—C angle at an Sn(...)Cl distance of 3.595 (1) Å. Weak inter­molecular C—H(...)O and C—H(...)Cl hydrogen bonding is present in the crystal structure.

Related literature

For a related structure, see: Vafaee et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m965-scheme1.jpg

Experimental

Crystal data

  • [Sn(CH3)(C6H5)(C10H8NO)Cl]
  • M r = 404.45
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m965-efi1.jpg
  • a = 8.9728 (4) Å
  • b = 13.1046 (6) Å
  • c = 14.0405 (6) Å
  • α = 106.621 (1)°
  • β = 92.764 (1)°
  • γ = 95.256 (1)°
  • V = 1570.52 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.79 mm−1
  • T = 100 K
  • 0.35 × 0.35 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.572, T max = 0.841
  • 15157 measured reflections
  • 7186 independent reflections
  • 6630 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.020
  • wR(F 2) = 0.057
  • S = 1.09
  • 7186 reflections
  • 383 parameters
  • H-atom parameters constrained
  • Δρmax = 0.51 e Å−3
  • Δρmin = −0.67 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027790/xu2800sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027790/xu2800Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The anion of 8-hydroxyquinoline is known to chelate to tin in organotin(IV) quinolinolates; however, for the chloroorganotin quinolinates, the chlorine atom participates in weak intermolecular bridging. Chloridomethylphenyl(quinolin-8-olato)tin exists as a dinuclear molecule owing to bridging by the anion (Vafaee et al., 2010). The methyl-substituted quinolin-8-olato derivative (Scheme I) consists of two independent molecules, and both have the N,O-chelated tin(IV) atom in a cis-C2SnNOCl trigonal bipyramidal geometry. The C18–Sn2–C19 and C1–Sn1–C2 bond angles are 124.82 (8) and 137.69 (8)°, respectively. The chlorine atom (Cl2) of the molecule with the smaller C–Sn–C angle interacts weakly with the tin atom (Sn1) of the molecule with the wider C–Sn–C angle at a distance of 3.595 (1) Å (Fig. 1). Weak intermolecular C—H···O and C—H···Cl hydrogen bonding is present in the crystal structure (Table 1).

Experimental

Methylphenyltin dichloride (0.35 g, 1 mmol) and 2-methyl-8-hydroxyquinoline (0.16 g, 1 mmol) were dissolved in methanol (10 ml) to give a faint yellow solution. The solution was set aside for the growth of crystals over a few days. Slow evaporation of methanol furnished crystals.

Refinement

Hydrogen atoms were placed in calculated positions (C–H 0.95–0.98 Å) and included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of SnCl(CH3)(C6H5)(C10H8NO) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The Cl2 atom is 3.595 (1) Å from Sn1, and it opens ...

Crystal data

[Sn(CH3)(C6H5)(C10H8NO)Cl]Z = 4
Mr = 404.45F(000) = 800
Triclinic, P1Dx = 1.711 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9728 (4) ÅCell parameters from 9971 reflections
b = 13.1046 (6) Åθ = 2.6–28.3°
c = 14.0405 (6) ŵ = 1.79 mm1
α = 106.621 (1)°T = 100 K
β = 92.764 (1)°Block, yellow
γ = 95.256 (1)°0.35 × 0.35 × 0.10 mm
V = 1570.52 (12) Å3

Data collection

Bruker SMART APEX diffractometer7186 independent reflections
Radiation source: fine-focus sealed tube6630 reflections with I > 2σ(I)
graphiteRint = 0.019
ω scansθmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.572, Tmax = 0.841k = −17→17
15157 measured reflectionsl = −18→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.020Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.057H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0305P)2 + 0.4536P] where P = (Fo2 + 2Fc2)/3
7186 reflections(Δ/σ)max = 0.001
383 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = −0.66 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Sn10.861340 (14)0.615377 (9)0.290747 (9)0.01263 (4)
Sn20.799527 (14)0.832410 (9)0.702160 (9)0.01230 (4)
Cl11.10698 (5)0.72185 (4)0.30174 (4)0.02216 (11)
Cl20.84380 (6)0.68692 (4)0.55666 (4)0.01948 (10)
O10.88484 (15)0.56320 (11)0.14165 (10)0.0167 (3)
O20.92261 (15)0.75531 (11)0.77964 (10)0.0158 (3)
N10.63791 (18)0.49944 (12)0.22228 (12)0.0135 (3)
N20.78441 (18)0.92597 (12)0.87127 (12)0.0143 (3)
C10.9407 (3)0.50330 (17)0.35798 (16)0.0225 (4)
H1A0.85900.47440.38990.034*
H1B1.02320.53880.40820.034*
H1C0.97680.44470.30700.034*
C20.7376 (2)0.75143 (15)0.33138 (14)0.0136 (4)
C30.5837 (2)0.74372 (15)0.30636 (14)0.0154 (4)
H30.53170.67620.27040.018*
C40.5052 (2)0.83317 (16)0.33318 (15)0.0186 (4)
H40.40040.82640.31570.022*
C50.5804 (2)0.93240 (16)0.38556 (16)0.0200 (4)
H50.52740.99380.40340.024*
C60.7327 (2)0.94134 (16)0.41155 (16)0.0205 (4)
H60.78421.00890.44800.025*
C70.8110 (2)0.85155 (15)0.38452 (15)0.0181 (4)
H70.91570.85860.40250.022*
C80.6448 (2)0.46140 (14)0.12108 (14)0.0128 (4)
C90.7758 (2)0.49533 (14)0.08082 (14)0.0131 (4)
C100.7884 (2)0.45633 (15)−0.02044 (14)0.0150 (4)
H100.87560.4781−0.04850.018*
C110.6728 (2)0.38445 (15)−0.08252 (15)0.0168 (4)
H110.68500.3569−0.15170.020*
C120.5437 (2)0.35347 (15)−0.04558 (15)0.0164 (4)
H120.46610.3064−0.08900.020*
C130.5265 (2)0.39227 (14)0.05808 (14)0.0141 (4)
C140.3962 (2)0.36966 (15)0.10369 (15)0.0167 (4)
H140.31180.32650.06410.020*
C150.3902 (2)0.40939 (15)0.20431 (15)0.0172 (4)
H150.30160.39440.23450.021*
C160.5159 (2)0.47280 (14)0.26363 (14)0.0154 (4)
C170.5142 (3)0.50856 (17)0.37524 (15)0.0223 (4)
H17A0.59130.56920.40340.033*
H17B0.53480.44930.40170.033*
H17C0.41540.53050.39340.033*
C180.9310 (3)0.95753 (17)0.66836 (16)0.0246 (5)
H18A0.89881.02650.70490.037*
H18B0.91840.94840.59660.037*
H18C1.03690.95580.68790.037*
C190.5611 (2)0.80153 (14)0.67682 (15)0.0143 (4)
C200.5010 (2)0.78133 (15)0.57891 (15)0.0184 (4)
H200.56600.78250.52770.022*
C210.3465 (2)0.75946 (16)0.55562 (17)0.0225 (4)
H210.30640.74770.48900.027*
C220.2512 (2)0.75486 (16)0.62948 (18)0.0237 (5)
H220.14590.73880.61350.028*
C230.3109 (2)0.77407 (16)0.72750 (17)0.0225 (4)
H230.24610.77030.77820.027*
C240.4646 (2)0.79866 (15)0.75122 (15)0.0172 (4)
H240.50420.81360.81840.021*
C250.8496 (2)0.87232 (14)0.92987 (14)0.0135 (4)
C260.9237 (2)0.78282 (14)0.87912 (14)0.0135 (4)
C270.9918 (2)0.72626 (15)0.93489 (15)0.0165 (4)
H271.04500.66810.90290.020*
C280.9827 (2)0.75434 (16)1.03909 (16)0.0191 (4)
H281.02890.71361.07600.023*
C290.9091 (2)0.83888 (16)1.08871 (15)0.0195 (4)
H290.90290.85551.15870.023*
C300.8425 (2)0.90100 (15)1.03417 (15)0.0169 (4)
C310.7673 (3)0.99163 (17)1.07720 (16)0.0224 (4)
H310.75851.01441.14710.027*
C320.7074 (3)1.04612 (16)1.01742 (16)0.0238 (5)
H320.65911.10791.04650.029*
C330.7165 (2)1.01183 (15)0.91330 (16)0.0183 (4)
C340.6501 (3)1.07147 (16)0.84782 (16)0.0236 (5)
H34A0.61221.02080.78340.035*
H34B0.72741.12430.83740.035*
H34C0.56731.10830.87990.035*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.01233 (7)0.01319 (7)0.01122 (7)0.00009 (5)0.00001 (5)0.00230 (5)
Sn20.01178 (7)0.01214 (7)0.01252 (7)−0.00020 (5)−0.00045 (5)0.00358 (5)
Cl10.0134 (2)0.0269 (2)0.0216 (2)−0.00386 (18)0.00076 (19)0.0016 (2)
Cl20.0179 (2)0.0228 (2)0.0148 (2)0.00503 (18)−0.00028 (18)0.00032 (18)
O10.0135 (7)0.0210 (7)0.0127 (7)−0.0030 (5)−0.0001 (5)0.0020 (5)
O20.0170 (7)0.0169 (6)0.0134 (7)0.0048 (5)0.0000 (5)0.0039 (5)
N10.0143 (8)0.0120 (7)0.0134 (8)−0.0001 (6)−0.0004 (6)0.0029 (6)
N20.0139 (8)0.0129 (7)0.0150 (8)−0.0003 (6)−0.0014 (6)0.0033 (6)
C10.0281 (12)0.0199 (10)0.0209 (10)0.0087 (8)0.0003 (9)0.0066 (8)
C20.0159 (9)0.0151 (8)0.0106 (8)0.0011 (7)0.0016 (7)0.0053 (7)
C30.0177 (10)0.0154 (9)0.0129 (9)−0.0011 (7)−0.0019 (7)0.0053 (7)
C40.0166 (10)0.0205 (9)0.0211 (10)0.0027 (8)−0.0005 (8)0.0099 (8)
C50.0250 (11)0.0164 (9)0.0210 (10)0.0049 (8)0.0034 (8)0.0080 (8)
C60.0232 (11)0.0142 (9)0.0219 (10)−0.0026 (8)0.0009 (8)0.0031 (8)
C70.0170 (10)0.0168 (9)0.0187 (10)−0.0025 (7)0.0010 (8)0.0038 (8)
C80.0138 (9)0.0107 (8)0.0139 (9)0.0029 (7)−0.0002 (7)0.0031 (7)
C90.0140 (9)0.0127 (8)0.0120 (9)0.0022 (7)−0.0007 (7)0.0028 (7)
C100.0125 (9)0.0189 (9)0.0146 (9)0.0037 (7)0.0017 (7)0.0057 (7)
C110.0205 (10)0.0160 (9)0.0125 (9)0.0053 (7)−0.0008 (7)0.0013 (7)
C120.0175 (10)0.0134 (8)0.0160 (9)0.0006 (7)−0.0038 (8)0.0018 (7)
C130.0151 (9)0.0105 (8)0.0161 (9)0.0026 (7)−0.0008 (7)0.0030 (7)
C140.0149 (9)0.0126 (8)0.0215 (10)−0.0025 (7)−0.0040 (8)0.0055 (7)
C150.0164 (10)0.0155 (9)0.0210 (10)−0.0015 (7)0.0025 (8)0.0086 (8)
C160.0177 (10)0.0117 (8)0.0166 (9)0.0005 (7)0.0031 (8)0.0041 (7)
C170.0251 (11)0.0218 (10)0.0180 (10)−0.0035 (8)0.0054 (8)0.0040 (8)
C180.0296 (12)0.0213 (10)0.0218 (11)−0.0083 (9)0.0000 (9)0.0084 (8)
C190.0130 (9)0.0103 (8)0.0183 (9)0.0005 (7)−0.0015 (7)0.0026 (7)
C200.0198 (10)0.0158 (9)0.0195 (10)0.0021 (7)−0.0016 (8)0.0055 (8)
C210.0195 (11)0.0199 (10)0.0255 (11)0.0028 (8)−0.0081 (9)0.0041 (8)
C220.0123 (10)0.0190 (9)0.0360 (12)0.0021 (8)−0.0020 (9)0.0023 (9)
C230.0174 (10)0.0168 (9)0.0314 (12)0.0027 (8)0.0072 (9)0.0029 (8)
C240.0179 (10)0.0138 (8)0.0186 (10)0.0022 (7)0.0014 (8)0.0023 (7)
C250.0130 (9)0.0119 (8)0.0145 (9)−0.0027 (7)−0.0030 (7)0.0041 (7)
C260.0100 (9)0.0134 (8)0.0166 (9)−0.0023 (7)−0.0001 (7)0.0050 (7)
C270.0154 (10)0.0158 (9)0.0189 (10)0.0013 (7)0.0004 (8)0.0063 (7)
C280.0192 (10)0.0190 (9)0.0203 (10)−0.0002 (8)−0.0037 (8)0.0094 (8)
C290.0237 (11)0.0209 (9)0.0127 (9)−0.0016 (8)−0.0025 (8)0.0046 (7)
C300.0187 (10)0.0151 (9)0.0148 (9)−0.0010 (7)−0.0014 (8)0.0021 (7)
C310.0275 (12)0.0201 (10)0.0157 (10)0.0037 (8)−0.0014 (8)−0.0009 (8)
C320.0280 (12)0.0176 (9)0.0212 (11)0.0072 (8)−0.0013 (9)−0.0024 (8)
C330.0180 (10)0.0122 (8)0.0224 (10)0.0014 (7)−0.0038 (8)0.0026 (7)
C340.0309 (12)0.0163 (9)0.0235 (11)0.0086 (8)−0.0032 (9)0.0048 (8)

Geometric parameters (Å, °)

Sn1—C12.116 (2)C14—C151.364 (3)
Sn1—C22.140 (2)C14—H140.9500
Sn1—N12.382 (2)C15—C161.414 (3)
Sn1—O12.036 (1)C15—H150.9500
Sn1—Cl12.4717 (5)C16—C171.503 (3)
Sn2—C182.110 (2)C17—H17A0.9800
Sn2—C192.134 (2)C17—H17B0.9800
Sn2—N22.357 (2)C17—H17C0.9800
Sn2—O22.035 (1)C18—H18A0.9800
Sn2—Cl22.4403 (5)C18—H18B0.9800
O1—C91.343 (2)C18—H18C0.9800
O2—C261.338 (2)C19—C201.394 (3)
N1—C161.328 (3)C19—C241.395 (3)
N1—C81.371 (2)C20—C211.393 (3)
N2—C331.329 (2)C20—H200.9500
N2—C251.369 (2)C21—C221.387 (3)
C1—H1A0.9800C21—H210.9500
C1—H1B0.9800C22—C231.397 (3)
C1—H1C0.9800C22—H220.9500
C2—C71.395 (3)C23—C241.389 (3)
C2—C31.395 (3)C23—H230.9500
C3—C41.392 (3)C24—H240.9500
C3—H30.9500C25—C301.410 (3)
C4—C51.390 (3)C25—C261.427 (3)
C4—H40.9500C26—C271.380 (3)
C5—C61.383 (3)C27—C281.411 (3)
C5—H50.9500C27—H270.9500
C6—C71.394 (3)C28—C291.374 (3)
C6—H60.9500C28—H280.9500
C7—H70.9500C29—C301.417 (3)
C8—C91.419 (3)C29—H290.9500
C8—C131.416 (3)C30—C311.416 (3)
C9—C101.380 (3)C31—C321.368 (3)
C10—C111.409 (3)C31—H310.9500
C10—H100.9500C32—C331.410 (3)
C11—C121.367 (3)C32—H320.9500
C11—H110.9500C33—C341.501 (3)
C12—C131.419 (3)C34—H34A0.9800
C12—H120.9500C34—H34B0.9800
C13—C141.409 (3)C34—H34C0.9800
O1—Sn1—C1108.71 (7)C15—C14—H14119.8
O1—Sn1—C2112.83 (6)C13—C14—H14119.8
C1—Sn1—C2137.69 (8)C14—C15—C16120.02 (18)
O1—Sn1—N175.16 (5)C14—C15—H15120.0
C1—Sn1—N191.64 (7)C16—C15—H15120.0
C2—Sn1—N191.31 (6)N1—C16—C15120.90 (18)
O1—Sn1—Cl185.61 (4)N1—C16—C17119.13 (18)
C1—Sn1—Cl195.99 (7)C15—C16—C17119.96 (18)
C2—Sn1—Cl194.87 (5)C16—C17—H17A109.5
N1—Sn1—Cl1160.71 (4)C16—C17—H17B109.5
O2—Sn2—C18112.03 (8)H17A—C17—H17B109.5
O2—Sn2—C19122.67 (7)C16—C17—H17C109.5
C18—Sn2—C19124.82 (8)H17A—C17—H17C109.5
O2—Sn2—N274.98 (5)H17B—C17—H17C109.5
C18—Sn2—N295.47 (7)Sn2—C18—H18A109.5
C19—Sn2—N291.97 (7)Sn2—C18—H18B109.5
O2—Sn2—Cl284.65 (4)H18A—C18—H18B109.5
C18—Sn2—Cl298.01 (6)Sn2—C18—H18C109.5
C19—Sn2—Cl293.80 (5)H18A—C18—H18C109.5
N2—Sn2—Cl2158.67 (4)H18B—C18—H18C109.5
C9—O1—Sn1119.74 (12)C20—C19—C24119.20 (18)
C26—O2—Sn2119.64 (11)C20—C19—Sn2116.76 (15)
C16—N1—C8119.70 (17)C24—C19—Sn2124.03 (14)
C16—N1—Sn1131.88 (13)C21—C20—C19120.5 (2)
C8—N1—Sn1108.34 (12)C21—C20—H20119.7
C33—N2—C25119.66 (17)C19—C20—H20119.7
C33—N2—Sn2130.84 (14)C22—C21—C20120.1 (2)
C25—N2—Sn2109.28 (12)C22—C21—H21119.9
Sn1—C1—H1A109.5C20—C21—H21119.9
Sn1—C1—H1B109.5C21—C22—C23119.53 (19)
H1A—C1—H1B109.5C21—C22—H22120.2
Sn1—C1—H1C109.5C23—C22—H22120.2
H1A—C1—H1C109.5C24—C23—C22120.4 (2)
H1B—C1—H1C109.5C24—C23—H23119.8
C7—C2—C3118.14 (17)C22—C23—H23119.8
C7—C2—Sn1119.86 (14)C23—C24—C19120.24 (19)
C3—C2—Sn1122.00 (13)C23—C24—H24119.9
C4—C3—C2121.18 (18)C19—C24—H24119.9
C4—C3—H3119.4N2—C25—C30122.83 (17)
C2—C3—H3119.4N2—C25—C26116.11 (17)
C5—C4—C3119.90 (19)C30—C25—C26121.05 (17)
C5—C4—H4120.1O2—C26—C27122.30 (17)
C3—C4—H4120.1O2—C26—C25119.32 (17)
C6—C5—C4119.67 (19)C27—C26—C25118.38 (17)
C6—C5—H5120.2C26—C27—C28120.38 (18)
C4—C5—H5120.2C26—C27—H27119.8
C5—C6—C7120.25 (19)C28—C27—H27119.8
C5—C6—H6119.9C29—C28—C27121.87 (18)
C7—C6—H6119.9C29—C28—H28119.1
C2—C7—C6120.86 (19)C27—C28—H28119.1
C2—C7—H7119.6C28—C29—C30119.20 (18)
C6—C7—H7119.6C28—C29—H29120.4
N1—C8—C9117.15 (17)C30—C29—H29120.4
N1—C8—C13122.24 (17)C25—C30—C29119.07 (18)
C9—C8—C13120.61 (17)C25—C30—C31116.50 (18)
O1—C9—C10121.69 (17)C29—C30—C31124.43 (19)
O1—C9—C8119.60 (17)C32—C31—C30119.56 (19)
C10—C9—C8118.71 (17)C32—C31—H31120.2
C9—C10—C11120.56 (18)C30—C31—H31120.2
C9—C10—H10119.7C31—C32—C33120.92 (19)
C11—C10—H10119.7C31—C32—H32119.5
C12—C11—C10121.57 (18)C33—C32—H32119.5
C12—C11—H11119.2N2—C33—C32120.46 (19)
C10—C11—H11119.2N2—C33—C34118.72 (18)
C11—C12—C13119.45 (18)C32—C33—C34120.82 (18)
C11—C12—H12120.3C33—C34—H34A109.5
C13—C12—H12120.3C33—C34—H34B109.5
C14—C13—C8116.55 (18)H34A—C34—H34B109.5
C14—C13—C12124.39 (18)C33—C34—H34C109.5
C8—C13—C12119.03 (18)H34A—C34—H34C109.5
C15—C14—C13120.41 (18)H34B—C34—H34C109.5
C1—Sn1—O1—C986.63 (15)C9—C8—C13—C122.8 (3)
C2—Sn1—O1—C9−85.08 (14)C11—C12—C13—C14177.05 (18)
N1—Sn1—O1—C9−0.01 (13)C11—C12—C13—C8−0.7 (3)
Cl1—Sn1—O1—C9−178.52 (13)C8—C13—C14—C15−3.0 (3)
C18—Sn2—O2—C2696.62 (15)C12—C13—C14—C15179.17 (18)
C19—Sn2—O2—C26−75.80 (15)C13—C14—C15—C16−0.6 (3)
N2—Sn2—O2—C266.74 (13)C8—N1—C16—C15−2.7 (3)
Cl2—Sn2—O2—C26−166.89 (13)Sn1—N1—C16—C15173.62 (13)
O1—Sn1—N1—C16−177.13 (18)C8—N1—C16—C17175.68 (17)
C1—Sn1—N1—C1673.95 (18)Sn1—N1—C16—C17−8.0 (3)
C2—Sn1—N1—C16−63.84 (17)C14—C15—C16—N13.7 (3)
Cl1—Sn1—N1—C16−172.62 (12)C14—C15—C16—C17−174.72 (18)
O1—Sn1—N1—C8−0.49 (11)O2—Sn2—C19—C20−129.96 (13)
C1—Sn1—N1—C8−109.41 (13)C18—Sn2—C19—C2058.60 (17)
C2—Sn1—N1—C8112.81 (12)N2—Sn2—C19—C20156.66 (14)
Cl1—Sn1—N1—C84.0 (2)Cl2—Sn2—C19—C20−43.89 (14)
O2—Sn2—N2—C33178.56 (19)O2—Sn2—C19—C2448.84 (17)
C18—Sn2—N2—C3367.19 (19)C18—Sn2—C19—C24−122.60 (16)
C19—Sn2—N2—C33−58.07 (18)N2—Sn2—C19—C24−24.54 (16)
Cl2—Sn2—N2—C33−163.77 (13)Cl2—Sn2—C19—C24134.91 (15)
O2—Sn2—N2—C25−6.99 (12)C24—C19—C20—C210.6 (3)
C18—Sn2—N2—C25−118.37 (14)Sn2—C19—C20—C21179.43 (14)
C19—Sn2—N2—C25116.37 (13)C19—C20—C21—C22−1.7 (3)
Cl2—Sn2—N2—C2510.7 (2)C20—C21—C22—C231.1 (3)
O1—Sn1—C2—C7−109.70 (15)C21—C22—C23—C240.6 (3)
C1—Sn1—C2—C782.00 (19)C22—C23—C24—C19−1.7 (3)
N1—Sn1—C2—C7175.87 (15)C20—C19—C24—C231.1 (3)
Cl1—Sn1—C2—C7−22.43 (15)Sn2—C19—C24—C23−177.64 (14)
O1—Sn1—C2—C370.31 (16)C33—N2—C25—C303.0 (3)
C1—Sn1—C2—C3−97.99 (18)Sn2—N2—C25—C30−172.16 (15)
N1—Sn1—C2—C3−4.12 (16)C33—N2—C25—C26−178.34 (17)
Cl1—Sn1—C2—C3157.58 (15)Sn2—N2—C25—C266.5 (2)
C7—C2—C3—C40.2 (3)Sn2—O2—C26—C27173.01 (14)
Sn1—C2—C3—C4−179.81 (15)Sn2—O2—C26—C25−5.7 (2)
C2—C3—C4—C50.2 (3)N2—C25—C26—O2−1.5 (3)
C3—C4—C5—C6−0.6 (3)C30—C25—C26—O2177.18 (17)
C4—C5—C6—C70.6 (3)N2—C25—C26—C27179.74 (17)
C3—C2—C7—C6−0.2 (3)C30—C25—C26—C27−1.6 (3)
Sn1—C2—C7—C6179.83 (15)O2—C26—C27—C28−176.31 (18)
C5—C6—C7—C2−0.2 (3)C25—C26—C27—C282.4 (3)
C16—N1—C8—C9178.02 (17)C26—C27—C28—C29−1.1 (3)
Sn1—N1—C8—C90.90 (19)C27—C28—C29—C30−1.1 (3)
C16—N1—C8—C13−1.2 (3)N2—C25—C30—C29178.00 (18)
Sn1—N1—C8—C13−178.32 (14)C26—C25—C30—C29−0.6 (3)
Sn1—O1—C9—C10−178.73 (13)N2—C25—C30—C31−1.9 (3)
Sn1—O1—C9—C80.5 (2)C26—C25—C30—C31179.53 (18)
N1—C8—C9—O1−1.0 (3)C28—C29—C30—C251.9 (3)
C13—C8—C9—O1178.21 (16)C28—C29—C30—C31−178.2 (2)
N1—C8—C9—C10178.27 (16)C25—C30—C31—C32−0.4 (3)
C13—C8—C9—C10−2.5 (3)C29—C30—C31—C32179.8 (2)
O1—C9—C10—C11179.46 (17)C30—C31—C32—C331.5 (3)
C8—C9—C10—C110.2 (3)C25—N2—C33—C32−1.8 (3)
C9—C10—C11—C121.9 (3)Sn2—N2—C33—C32172.16 (15)
C10—C11—C12—C13−1.6 (3)C25—N2—C33—C34178.06 (18)
N1—C8—C13—C144.0 (3)Sn2—N2—C33—C34−8.0 (3)
C9—C8—C13—C14−175.16 (16)C31—C32—C33—N2−0.4 (3)
N1—C8—C13—C12−178.03 (16)C31—C32—C33—C34179.7 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4···Cl1i0.952.833.6898 (19)152
C22—H22···Cl2i0.952.763.705 (2)177
C10—H10···O1ii0.952.593.454 (2)152

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2800).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Vafaee, M., Amini, M. M. & Ng, S. W. (2010). Acta Cryst. E66, m964. [PMC free article] [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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