Chloridometh­yl(2-methyl­quinolin-8-olato-κ2N,O)phenyl­tin(IV)

Vafaee, M.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536810027790

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m965

https://doi.org/10.1107/S1600536810027790

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Chloridomethyl(2-methylquinolin-8-olato-κ²N,O)phenyltin(IV)

Maryam Vafaee,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 12 July 2010; accepted 13 July 2010; online 17 July 2010)

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 Sn^IV 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 Sn^IV 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 ).

Experimental

Crystal data

[Sn(CH₃)(C₆H₅)(C₁₀H₈NO)Cl]
M_r = 404.45
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.020
wR(F²) = 0.057
S = 1.09
7186 reflections
383 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cl1ⁱ	0.95	2.83	3.6898 (19)	152
C22—H22⋯Cl2ⁱ	0.95	2.76	3.705 (2)	177
C10—H10⋯O1ⁱⁱ	0.95	2.59	3.454 (2)	152
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y+1, -z.

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

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027790/xu2800Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

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

Figures top

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 the C–Sn–C angle to 137.69 (8) °.

Chloridomethyl(2-methylquinolin-8-olato-κ²N,O)phenyltin(IV) top

Crystal data top

[Sn(CH₃)(C₆H₅)(C₁₀H₈NO)Cl]	Z = 4
M_r = 404.45	F(000) = 800
Triclinic, P1	D_x = 1.711 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9728 (4) Å	Cell parameters from 9971 reflections
b = 13.1046 (6) Å	θ = 2.6–28.3°
c = 14.0405 (6) Å	µ = 1.79 mm⁻¹
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 top

Bruker SMART APEX diffractometer	7186 independent reflections
Radiation source: fine-focus sealed tube	6630 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.572, T_max = 0.841	k = −17→17
15157 measured reflections	l = −18→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.057	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0305P)² + 0.4536P] where P = (F_o² + 2F_c²)/3
7186 reflections	(Δ/σ)_max = 0.001
383 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

[Sn(CH₃)(C₆H₅)(C₁₀H₈NO)Cl]	γ = 95.256 (1)°
M_r = 404.45	V = 1570.52 (12) Å³
Triclinic, P1	Z = 4
a = 8.9728 (4) Å	Mo Kα radiation
b = 13.1046 (6) Å	µ = 1.79 mm⁻¹
c = 14.0405 (6) Å	T = 100 K
α = 106.621 (1)°	0.35 × 0.35 × 0.10 mm
β = 92.764 (1)°

Data collection top

Bruker SMART APEX diffractometer	7186 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6630 reflections with I > 2σ(I)
T_min = 0.572, T_max = 0.841	R_int = 0.019
15157 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	0 restraints
wR(F²) = 0.057	H-atom parameters constrained
S = 1.09	Δρ_max = 0.51 e Å⁻³
7186 reflections	Δρ_min = −0.67 e Å⁻³
383 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.861340 (14)	0.615377 (9)	0.290747 (9)	0.01263 (4)
Sn2	0.799527 (14)	0.832410 (9)	0.702160 (9)	0.01230 (4)
Cl1	1.10698 (5)	0.72185 (4)	0.30174 (4)	0.02216 (11)
Cl2	0.84380 (6)	0.68692 (4)	0.55666 (4)	0.01948 (10)
O1	0.88484 (15)	0.56320 (11)	0.14165 (10)	0.0167 (3)
O2	0.92261 (15)	0.75531 (11)	0.77964 (10)	0.0158 (3)
N1	0.63791 (18)	0.49944 (12)	0.22228 (12)	0.0135 (3)
N2	0.78441 (18)	0.92597 (12)	0.87127 (12)	0.0143 (3)
C1	0.9407 (3)	0.50330 (17)	0.35798 (16)	0.0225 (4)
H1A	0.8590	0.4744	0.3899	0.034*
H1B	1.0232	0.5388	0.4082	0.034*
H1C	0.9768	0.4447	0.3070	0.034*
C2	0.7376 (2)	0.75143 (15)	0.33138 (14)	0.0136 (4)
C3	0.5837 (2)	0.74372 (15)	0.30636 (14)	0.0154 (4)
H3	0.5317	0.6762	0.2704	0.018*
C4	0.5052 (2)	0.83317 (16)	0.33318 (15)	0.0186 (4)
H4	0.4004	0.8264	0.3157	0.022*
C5	0.5804 (2)	0.93240 (16)	0.38556 (16)	0.0200 (4)
H5	0.5274	0.9938	0.4034	0.024*
C6	0.7327 (2)	0.94134 (16)	0.41155 (16)	0.0205 (4)
H6	0.7842	1.0089	0.4480	0.025*
C7	0.8110 (2)	0.85155 (15)	0.38452 (15)	0.0181 (4)
H7	0.9157	0.8586	0.4025	0.022*
C8	0.6448 (2)	0.46140 (14)	0.12108 (14)	0.0128 (4)
C9	0.7758 (2)	0.49533 (14)	0.08082 (14)	0.0131 (4)
C10	0.7884 (2)	0.45633 (15)	−0.02044 (14)	0.0150 (4)
H10	0.8756	0.4781	−0.0485	0.018*
C11	0.6728 (2)	0.38445 (15)	−0.08252 (15)	0.0168 (4)
H11	0.6850	0.3569	−0.1517	0.020*
C12	0.5437 (2)	0.35347 (15)	−0.04558 (15)	0.0164 (4)
H12	0.4661	0.3064	−0.0890	0.020*
C13	0.5265 (2)	0.39227 (14)	0.05808 (14)	0.0141 (4)
C14	0.3962 (2)	0.36966 (15)	0.10369 (15)	0.0167 (4)
H14	0.3118	0.3265	0.0641	0.020*
C15	0.3902 (2)	0.40939 (15)	0.20431 (15)	0.0172 (4)
H15	0.3016	0.3944	0.2345	0.021*
C16	0.5159 (2)	0.47280 (14)	0.26363 (14)	0.0154 (4)
C17	0.5142 (3)	0.50856 (17)	0.37524 (15)	0.0223 (4)
H17A	0.5913	0.5692	0.4034	0.033*
H17B	0.5348	0.4493	0.4017	0.033*
H17C	0.4154	0.5305	0.3934	0.033*
C18	0.9310 (3)	0.95753 (17)	0.66836 (16)	0.0246 (5)
H18A	0.8988	1.0265	0.7049	0.037*
H18B	0.9184	0.9484	0.5966	0.037*
H18C	1.0369	0.9558	0.6879	0.037*
C19	0.5611 (2)	0.80153 (14)	0.67682 (15)	0.0143 (4)
C20	0.5010 (2)	0.78133 (15)	0.57891 (15)	0.0184 (4)
H20	0.5660	0.7825	0.5277	0.022*
C21	0.3465 (2)	0.75946 (16)	0.55562 (17)	0.0225 (4)
H21	0.3064	0.7477	0.4890	0.027*
C22	0.2512 (2)	0.75486 (16)	0.62948 (18)	0.0237 (5)
H22	0.1459	0.7388	0.6135	0.028*
C23	0.3109 (2)	0.77407 (16)	0.72750 (17)	0.0225 (4)
H23	0.2461	0.7703	0.7782	0.027*
C24	0.4646 (2)	0.79866 (15)	0.75122 (15)	0.0172 (4)
H24	0.5042	0.8136	0.8184	0.021*
C25	0.8496 (2)	0.87232 (14)	0.92987 (14)	0.0135 (4)
C26	0.9237 (2)	0.78282 (14)	0.87912 (14)	0.0135 (4)
C27	0.9918 (2)	0.72626 (15)	0.93489 (15)	0.0165 (4)
H27	1.0450	0.6681	0.9029	0.020*
C28	0.9827 (2)	0.75434 (16)	1.03909 (16)	0.0191 (4)
H28	1.0289	0.7136	1.0760	0.023*
C29	0.9091 (2)	0.83888 (16)	1.08871 (15)	0.0195 (4)
H29	0.9029	0.8555	1.1587	0.023*
C30	0.8425 (2)	0.90100 (15)	1.03417 (15)	0.0169 (4)
C31	0.7673 (3)	0.99163 (17)	1.07720 (16)	0.0224 (4)
H31	0.7585	1.0144	1.1471	0.027*
C32	0.7074 (3)	1.04612 (16)	1.01742 (16)	0.0238 (5)
H32	0.6591	1.1079	1.0465	0.029*
C33	0.7165 (2)	1.01183 (15)	0.91330 (16)	0.0183 (4)
C34	0.6501 (3)	1.07147 (16)	0.84782 (16)	0.0236 (5)
H34A	0.6122	1.0208	0.7834	0.035*
H34B	0.7274	1.1243	0.8374	0.035*
H34C	0.5673	1.1083	0.8799	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01233 (7)	0.01319 (7)	0.01122 (7)	0.00009 (5)	0.00001 (5)	0.00230 (5)
Sn2	0.01178 (7)	0.01214 (7)	0.01252 (7)	−0.00020 (5)	−0.00045 (5)	0.00358 (5)
Cl1	0.0134 (2)	0.0269 (2)	0.0216 (2)	−0.00386 (18)	0.00076 (19)	0.0016 (2)
Cl2	0.0179 (2)	0.0228 (2)	0.0148 (2)	0.00503 (18)	−0.00028 (18)	0.00032 (18)
O1	0.0135 (7)	0.0210 (7)	0.0127 (7)	−0.0030 (5)	−0.0001 (5)	0.0020 (5)
O2	0.0170 (7)	0.0169 (6)	0.0134 (7)	0.0048 (5)	0.0000 (5)	0.0039 (5)
N1	0.0143 (8)	0.0120 (7)	0.0134 (8)	−0.0001 (6)	−0.0004 (6)	0.0029 (6)
N2	0.0139 (8)	0.0129 (7)	0.0150 (8)	−0.0003 (6)	−0.0014 (6)	0.0033 (6)
C1	0.0281 (12)	0.0199 (10)	0.0209 (10)	0.0087 (8)	0.0003 (9)	0.0066 (8)
C2	0.0159 (9)	0.0151 (8)	0.0106 (8)	0.0011 (7)	0.0016 (7)	0.0053 (7)
C3	0.0177 (10)	0.0154 (9)	0.0129 (9)	−0.0011 (7)	−0.0019 (7)	0.0053 (7)
C4	0.0166 (10)	0.0205 (9)	0.0211 (10)	0.0027 (8)	−0.0005 (8)	0.0099 (8)
C5	0.0250 (11)	0.0164 (9)	0.0210 (10)	0.0049 (8)	0.0034 (8)	0.0080 (8)
C6	0.0232 (11)	0.0142 (9)	0.0219 (10)	−0.0026 (8)	0.0009 (8)	0.0031 (8)
C7	0.0170 (10)	0.0168 (9)	0.0187 (10)	−0.0025 (7)	0.0010 (8)	0.0038 (8)
C8	0.0138 (9)	0.0107 (8)	0.0139 (9)	0.0029 (7)	−0.0002 (7)	0.0031 (7)
C9	0.0140 (9)	0.0127 (8)	0.0120 (9)	0.0022 (7)	−0.0007 (7)	0.0028 (7)
C10	0.0125 (9)	0.0189 (9)	0.0146 (9)	0.0037 (7)	0.0017 (7)	0.0057 (7)
C11	0.0205 (10)	0.0160 (9)	0.0125 (9)	0.0053 (7)	−0.0008 (7)	0.0013 (7)
C12	0.0175 (10)	0.0134 (8)	0.0160 (9)	0.0006 (7)	−0.0038 (8)	0.0018 (7)
C13	0.0151 (9)	0.0105 (8)	0.0161 (9)	0.0026 (7)	−0.0008 (7)	0.0030 (7)
C14	0.0149 (9)	0.0126 (8)	0.0215 (10)	−0.0025 (7)	−0.0040 (8)	0.0055 (7)
C15	0.0164 (10)	0.0155 (9)	0.0210 (10)	−0.0015 (7)	0.0025 (8)	0.0086 (8)
C16	0.0177 (10)	0.0117 (8)	0.0166 (9)	0.0005 (7)	0.0031 (8)	0.0041 (7)
C17	0.0251 (11)	0.0218 (10)	0.0180 (10)	−0.0035 (8)	0.0054 (8)	0.0040 (8)
C18	0.0296 (12)	0.0213 (10)	0.0218 (11)	−0.0083 (9)	0.0000 (9)	0.0084 (8)
C19	0.0130 (9)	0.0103 (8)	0.0183 (9)	0.0005 (7)	−0.0015 (7)	0.0026 (7)
C20	0.0198 (10)	0.0158 (9)	0.0195 (10)	0.0021 (7)	−0.0016 (8)	0.0055 (8)
C21	0.0195 (11)	0.0199 (10)	0.0255 (11)	0.0028 (8)	−0.0081 (9)	0.0041 (8)
C22	0.0123 (10)	0.0190 (9)	0.0360 (12)	0.0021 (8)	−0.0020 (9)	0.0023 (9)
C23	0.0174 (10)	0.0168 (9)	0.0314 (12)	0.0027 (8)	0.0072 (9)	0.0029 (8)
C24	0.0179 (10)	0.0138 (8)	0.0186 (10)	0.0022 (7)	0.0014 (8)	0.0023 (7)
C25	0.0130 (9)	0.0119 (8)	0.0145 (9)	−0.0027 (7)	−0.0030 (7)	0.0041 (7)
C26	0.0100 (9)	0.0134 (8)	0.0166 (9)	−0.0023 (7)	−0.0001 (7)	0.0050 (7)
C27	0.0154 (10)	0.0158 (9)	0.0189 (10)	0.0013 (7)	0.0004 (8)	0.0063 (7)
C28	0.0192 (10)	0.0190 (9)	0.0203 (10)	−0.0002 (8)	−0.0037 (8)	0.0094 (8)
C29	0.0237 (11)	0.0209 (9)	0.0127 (9)	−0.0016 (8)	−0.0025 (8)	0.0046 (7)
C30	0.0187 (10)	0.0151 (9)	0.0148 (9)	−0.0010 (7)	−0.0014 (8)	0.0021 (7)
C31	0.0275 (12)	0.0201 (10)	0.0157 (10)	0.0037 (8)	−0.0014 (8)	−0.0009 (8)
C32	0.0280 (12)	0.0176 (9)	0.0212 (11)	0.0072 (8)	−0.0013 (9)	−0.0024 (8)
C33	0.0180 (10)	0.0122 (8)	0.0224 (10)	0.0014 (7)	−0.0038 (8)	0.0026 (7)
C34	0.0309 (12)	0.0163 (9)	0.0235 (11)	0.0086 (8)	−0.0032 (9)	0.0048 (8)

Geometric parameters (Å, º) top

Sn1—C1	2.116 (2)	C14—C15	1.364 (3)
Sn1—C2	2.140 (2)	C14—H14	0.9500
Sn1—N1	2.382 (2)	C15—C16	1.414 (3)
Sn1—O1	2.036 (1)	C15—H15	0.9500
Sn1—Cl1	2.4717 (5)	C16—C17	1.503 (3)
Sn2—C18	2.110 (2)	C17—H17A	0.9800
Sn2—C19	2.134 (2)	C17—H17B	0.9800
Sn2—N2	2.357 (2)	C17—H17C	0.9800
Sn2—O2	2.035 (1)	C18—H18A	0.9800
Sn2—Cl2	2.4403 (5)	C18—H18B	0.9800
O1—C9	1.343 (2)	C18—H18C	0.9800
O2—C26	1.338 (2)	C19—C20	1.394 (3)
N1—C16	1.328 (3)	C19—C24	1.395 (3)
N1—C8	1.371 (2)	C20—C21	1.393 (3)
N2—C33	1.329 (2)	C20—H20	0.9500
N2—C25	1.369 (2)	C21—C22	1.387 (3)
C1—H1A	0.9800	C21—H21	0.9500
C1—H1B	0.9800	C22—C23	1.397 (3)
C1—H1C	0.9800	C22—H22	0.9500
C2—C7	1.395 (3)	C23—C24	1.389 (3)
C2—C3	1.395 (3)	C23—H23	0.9500
C3—C4	1.392 (3)	C24—H24	0.9500
C3—H3	0.9500	C25—C30	1.410 (3)
C4—C5	1.390 (3)	C25—C26	1.427 (3)
C4—H4	0.9500	C26—C27	1.380 (3)
C5—C6	1.383 (3)	C27—C28	1.411 (3)
C5—H5	0.9500	C27—H27	0.9500
C6—C7	1.394 (3)	C28—C29	1.374 (3)
C6—H6	0.9500	C28—H28	0.9500
C7—H7	0.9500	C29—C30	1.417 (3)
C8—C9	1.419 (3)	C29—H29	0.9500
C8—C13	1.416 (3)	C30—C31	1.416 (3)
C9—C10	1.380 (3)	C31—C32	1.368 (3)
C10—C11	1.409 (3)	C31—H31	0.9500
C10—H10	0.9500	C32—C33	1.410 (3)
C11—C12	1.367 (3)	C32—H32	0.9500
C11—H11	0.9500	C33—C34	1.501 (3)
C12—C13	1.419 (3)	C34—H34A	0.9800
C12—H12	0.9500	C34—H34B	0.9800
C13—C14	1.409 (3)	C34—H34C	0.9800

O1—Sn1—C1	108.71 (7)	C15—C14—H14	119.8
O1—Sn1—C2	112.83 (6)	C13—C14—H14	119.8
C1—Sn1—C2	137.69 (8)	C14—C15—C16	120.02 (18)
O1—Sn1—N1	75.16 (5)	C14—C15—H15	120.0
C1—Sn1—N1	91.64 (7)	C16—C15—H15	120.0
C2—Sn1—N1	91.31 (6)	N1—C16—C15	120.90 (18)
O1—Sn1—Cl1	85.61 (4)	N1—C16—C17	119.13 (18)
C1—Sn1—Cl1	95.99 (7)	C15—C16—C17	119.96 (18)
C2—Sn1—Cl1	94.87 (5)	C16—C17—H17A	109.5
N1—Sn1—Cl1	160.71 (4)	C16—C17—H17B	109.5
O2—Sn2—C18	112.03 (8)	H17A—C17—H17B	109.5
O2—Sn2—C19	122.67 (7)	C16—C17—H17C	109.5
C18—Sn2—C19	124.82 (8)	H17A—C17—H17C	109.5
O2—Sn2—N2	74.98 (5)	H17B—C17—H17C	109.5
C18—Sn2—N2	95.47 (7)	Sn2—C18—H18A	109.5
C19—Sn2—N2	91.97 (7)	Sn2—C18—H18B	109.5
O2—Sn2—Cl2	84.65 (4)	H18A—C18—H18B	109.5
C18—Sn2—Cl2	98.01 (6)	Sn2—C18—H18C	109.5
C19—Sn2—Cl2	93.80 (5)	H18A—C18—H18C	109.5
N2—Sn2—Cl2	158.67 (4)	H18B—C18—H18C	109.5
C9—O1—Sn1	119.74 (12)	C20—C19—C24	119.20 (18)
C26—O2—Sn2	119.64 (11)	C20—C19—Sn2	116.76 (15)
C16—N1—C8	119.70 (17)	C24—C19—Sn2	124.03 (14)
C16—N1—Sn1	131.88 (13)	C21—C20—C19	120.5 (2)
C8—N1—Sn1	108.34 (12)	C21—C20—H20	119.7
C33—N2—C25	119.66 (17)	C19—C20—H20	119.7
C33—N2—Sn2	130.84 (14)	C22—C21—C20	120.1 (2)
C25—N2—Sn2	109.28 (12)	C22—C21—H21	119.9
Sn1—C1—H1A	109.5	C20—C21—H21	119.9
Sn1—C1—H1B	109.5	C21—C22—C23	119.53 (19)
H1A—C1—H1B	109.5	C21—C22—H22	120.2
Sn1—C1—H1C	109.5	C23—C22—H22	120.2
H1A—C1—H1C	109.5	C24—C23—C22	120.4 (2)
H1B—C1—H1C	109.5	C24—C23—H23	119.8
C7—C2—C3	118.14 (17)	C22—C23—H23	119.8
C7—C2—Sn1	119.86 (14)	C23—C24—C19	120.24 (19)
C3—C2—Sn1	122.00 (13)	C23—C24—H24	119.9
C4—C3—C2	121.18 (18)	C19—C24—H24	119.9
C4—C3—H3	119.4	N2—C25—C30	122.83 (17)
C2—C3—H3	119.4	N2—C25—C26	116.11 (17)
C5—C4—C3	119.90 (19)	C30—C25—C26	121.05 (17)
C5—C4—H4	120.1	O2—C26—C27	122.30 (17)
C3—C4—H4	120.1	O2—C26—C25	119.32 (17)
C6—C5—C4	119.67 (19)	C27—C26—C25	118.38 (17)
C6—C5—H5	120.2	C26—C27—C28	120.38 (18)
C4—C5—H5	120.2	C26—C27—H27	119.8
C5—C6—C7	120.25 (19)	C28—C27—H27	119.8
C5—C6—H6	119.9	C29—C28—C27	121.87 (18)
C7—C6—H6	119.9	C29—C28—H28	119.1
C2—C7—C6	120.86 (19)	C27—C28—H28	119.1
C2—C7—H7	119.6	C28—C29—C30	119.20 (18)
C6—C7—H7	119.6	C28—C29—H29	120.4
N1—C8—C9	117.15 (17)	C30—C29—H29	120.4
N1—C8—C13	122.24 (17)	C25—C30—C29	119.07 (18)
C9—C8—C13	120.61 (17)	C25—C30—C31	116.50 (18)
O1—C9—C10	121.69 (17)	C29—C30—C31	124.43 (19)
O1—C9—C8	119.60 (17)	C32—C31—C30	119.56 (19)
C10—C9—C8	118.71 (17)	C32—C31—H31	120.2
C9—C10—C11	120.56 (18)	C30—C31—H31	120.2
C9—C10—H10	119.7	C31—C32—C33	120.92 (19)
C11—C10—H10	119.7	C31—C32—H32	119.5
C12—C11—C10	121.57 (18)	C33—C32—H32	119.5
C12—C11—H11	119.2	N2—C33—C32	120.46 (19)
C10—C11—H11	119.2	N2—C33—C34	118.72 (18)
C11—C12—C13	119.45 (18)	C32—C33—C34	120.82 (18)
C11—C12—H12	120.3	C33—C34—H34A	109.5
C13—C12—H12	120.3	C33—C34—H34B	109.5
C14—C13—C8	116.55 (18)	H34A—C34—H34B	109.5
C14—C13—C12	124.39 (18)	C33—C34—H34C	109.5
C8—C13—C12	119.03 (18)	H34A—C34—H34C	109.5
C15—C14—C13	120.41 (18)	H34B—C34—H34C	109.5

C1—Sn1—O1—C9	86.63 (15)	C9—C8—C13—C12	2.8 (3)
C2—Sn1—O1—C9	−85.08 (14)	C11—C12—C13—C14	177.05 (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—C26	96.62 (15)	C12—C13—C14—C15	179.17 (18)
C19—Sn2—O2—C26	−75.80 (15)	C13—C14—C15—C16	−0.6 (3)
N2—Sn2—O2—C26	6.74 (13)	C8—N1—C16—C15	−2.7 (3)
Cl2—Sn2—O2—C26	−166.89 (13)	Sn1—N1—C16—C15	173.62 (13)
O1—Sn1—N1—C16	−177.13 (18)	C8—N1—C16—C17	175.68 (17)
C1—Sn1—N1—C16	73.95 (18)	Sn1—N1—C16—C17	−8.0 (3)
C2—Sn1—N1—C16	−63.84 (17)	C14—C15—C16—N1	3.7 (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—C20	58.60 (17)
C2—Sn1—N1—C8	112.81 (12)	N2—Sn2—C19—C20	156.66 (14)
Cl1—Sn1—N1—C8	4.0 (2)	Cl2—Sn2—C19—C20	−43.89 (14)
O2—Sn2—N2—C33	178.56 (19)	O2—Sn2—C19—C24	48.84 (17)
C18—Sn2—N2—C33	67.19 (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—C24	134.91 (15)
O2—Sn2—N2—C25	−6.99 (12)	C24—C19—C20—C21	0.6 (3)
C18—Sn2—N2—C25	−118.37 (14)	Sn2—C19—C20—C21	179.43 (14)
C19—Sn2—N2—C25	116.37 (13)	C19—C20—C21—C22	−1.7 (3)
Cl2—Sn2—N2—C25	10.7 (2)	C20—C21—C22—C23	1.1 (3)
O1—Sn1—C2—C7	−109.70 (15)	C21—C22—C23—C24	0.6 (3)
C1—Sn1—C2—C7	82.00 (19)	C22—C23—C24—C19	−1.7 (3)
N1—Sn1—C2—C7	175.87 (15)	C20—C19—C24—C23	1.1 (3)
Cl1—Sn1—C2—C7	−22.43 (15)	Sn2—C19—C24—C23	−177.64 (14)
O1—Sn1—C2—C3	70.31 (16)	C33—N2—C25—C30	3.0 (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—C3	157.58 (15)	Sn2—N2—C25—C26	6.5 (2)
C7—C2—C3—C4	0.2 (3)	Sn2—O2—C26—C27	173.01 (14)
Sn1—C2—C3—C4	−179.81 (15)	Sn2—O2—C26—C25	−5.7 (2)
C2—C3—C4—C5	0.2 (3)	N2—C25—C26—O2	−1.5 (3)
C3—C4—C5—C6	−0.6 (3)	C30—C25—C26—O2	177.18 (17)
C4—C5—C6—C7	0.6 (3)	N2—C25—C26—C27	179.74 (17)
C3—C2—C7—C6	−0.2 (3)	C30—C25—C26—C27	−1.6 (3)
Sn1—C2—C7—C6	179.83 (15)	O2—C26—C27—C28	−176.31 (18)
C5—C6—C7—C2	−0.2 (3)	C25—C26—C27—C28	2.4 (3)
C16—N1—C8—C9	178.02 (17)	C26—C27—C28—C29	−1.1 (3)
Sn1—N1—C8—C9	0.90 (19)	C27—C28—C29—C30	−1.1 (3)
C16—N1—C8—C13	−1.2 (3)	N2—C25—C30—C29	178.00 (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—C8	0.5 (2)	C26—C25—C30—C31	179.53 (18)
N1—C8—C9—O1	−1.0 (3)	C28—C29—C30—C25	1.9 (3)
C13—C8—C9—O1	178.21 (16)	C28—C29—C30—C31	−178.2 (2)
N1—C8—C9—C10	178.27 (16)	C25—C30—C31—C32	−0.4 (3)
C13—C8—C9—C10	−2.5 (3)	C29—C30—C31—C32	179.8 (2)
O1—C9—C10—C11	179.46 (17)	C30—C31—C32—C33	1.5 (3)
C8—C9—C10—C11	0.2 (3)	C25—N2—C33—C32	−1.8 (3)
C9—C10—C11—C12	1.9 (3)	Sn2—N2—C33—C32	172.16 (15)
C10—C11—C12—C13	−1.6 (3)	C25—N2—C33—C34	178.06 (18)
N1—C8—C13—C14	4.0 (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—C34	179.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cl1ⁱ	0.95	2.83	3.6898 (19)	152
C22—H22···Cl2ⁱ	0.95	2.76	3.705 (2)	177
C10—H10···O1ⁱⁱ	0.95	2.59	3.454 (2)	152

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

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)(C₆H₅)(C₁₀H₈NO)Cl]
M_r	404.45
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.9728 (4), 13.1046 (6), 14.0405 (6)
α, β, γ (°)	106.621 (1), 92.764 (1), 95.256 (1)
V (Å³)	1570.52 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.79
Crystal size (mm)	0.35 × 0.35 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.572, 0.841
No. of measured, independent and observed [I > 2σ(I)] reflections	15157, 7186, 6630
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.057, 1.09
No. of reflections	7186
No. of parameters	383
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.67

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cl1ⁱ	0.95	2.83	3.6898 (19)	152
C22—H22···Cl2ⁱ	0.95	2.76	3.705 (2)	177
C10—H10···O1ⁱⁱ	0.95	2.59	3.454 (2)	152

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

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vafaee, M., Amini, M. M. & Ng, S. W. (2010). Acta Cryst. E66, m964. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar