Dichloridobis(4-chloro­benz­yl)(4,4′-dimethyl-2,2′-bipyridine-κ2N,N′)tin(IV)

Keng, T.C.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536809049381

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1676

doi:10.1107/S1600536809049381

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Dichloridobis(4-chlorobenzyl)(4,4′-dimethyl-2,2′-bipyridine-κ²N,N′)tin(IV)

Thy Chun Keng,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 18 November 2009; accepted 18 November 2009; online 25 November 2009)

The Sn^IV atom in the title compound, [Sn(C₇H₆Cl)₂Cl₂(C₁₂H₁₂N₂)], is coordinated by the bidentate N-heterocycle molecule, two chlorobenzyl anions and two Cl⁻ anions in a distorted trans-C₂SnCl₂N₂ octahedral geometry [C—Sn—C = 178.4 (1)°]. In the molecular structure, the two benzene rings are oriented at a dihedral angle of 39.62 (17)°.

Related literature

For the synthesis of bis(4-chlorobenzyl)tin dichloride, see: Sisido et al. (1961 ). For the 1,10-phenanthroline adduct, see: Tan et al. (2009 ).

Experimental

Crystal data

[Sn(C₇H₆Cl)₂Cl₂(C₁₂H₁₂N₂)]
M_r = 624.96
Monoclinic, P 2₁ /n
a = 11.4035 (6) Å
b = 14.6804 (8) Å
c = 16.9270 (9) Å
β = 101.9182 (9)°
V = 2772.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.32 mm⁻¹
T = 293 K
0.30 × 0.28 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.692, T_max = 0.778
15766 measured reflections
6263 independent reflections
4883 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.095
S = 1.00
6263 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049381/xu2682sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049381/xu2682Isup2.hkl

checkCIF report

Related literature top

For the synthesis of bis(4-chlorobenzyl)tin dichloride, see: Sisido et al. (1961). For the 1,10-phenanthroline adduct, see: Tan et al. (2009).

Experimental top

Di(4-chlorobenzyl)tin dichloride was synthesized by the reaction of 4-chlorobenzyl chloride and metallic tin (Sisido et al.). The diorganotin compound (0.44 g, 1 mmol) and 4,4'-dimethyl-2,2'-bipyridine (0.18 g, 1 mmol) was heated in chloroform (30 ml) for 1 h. Faint-yellow crystals separated upon slow evaporation of the solvent.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of SnCl₂(C₁₀H₁₂N₂)(C₇H₆Cl)₂ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Dichloridobis(4-chlorobenzyl)(4,4'-dimethyl-2,2'-bipyridine- κ²N,N')tin(IV) top

Crystal data top

[Sn(C₇H₆Cl)₂Cl₂(C₁₂H₁₂N₂)]	F(000) = 1248
M_r = 624.96	D_x = 1.497 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6177 reflections
a = 11.4035 (6) Å	θ = 2.4–28.3°
b = 14.6804 (8) Å	µ = 1.32 mm⁻¹
c = 16.9270 (9) Å	T = 293 K
β = 101.9182 (9)°	Block, pale yellow
V = 2772.6 (3) Å³	0.30 × 0.28 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	6263 independent reflections
Radiation source: fine-focus sealed tube	4883 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.692, T_max = 0.778	k = −19→18
15766 measured reflections	l = −21→17

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0523P)² + 1.1119P] where P = (F_o² + 2F_c²)/3
6263 reflections	(Δ/σ)_max = 0.001
300 parameters	Δρ_max = 0.78 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Sn(C₇H₆Cl)₂Cl₂(C₁₂H₁₂N₂)]	V = 2772.6 (3) Å³
M_r = 624.96	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.4035 (6) Å	µ = 1.32 mm⁻¹
b = 14.6804 (8) Å	T = 293 K
c = 16.9270 (9) Å	0.30 × 0.28 × 0.20 mm
β = 101.9182 (9)°

Data collection top

Bruker SMART APEX diffractometer	6263 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4883 reflections with I > 2σ(I)
T_min = 0.692, T_max = 0.778	R_int = 0.017
15766 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.00	Δρ_max = 0.78 e Å⁻³
6263 reflections	Δρ_min = −0.49 e Å⁻³
300 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.278374 (15)	0.231209 (14)	0.536683 (11)	0.05372 (8)
Cl1	0.06174 (7)	0.19394 (9)	0.52457 (7)	0.0993 (3)
Cl2	0.28579 (8)	0.31620 (8)	0.40783 (5)	0.0894 (3)
Cl3	0.35723 (13)	−0.23372 (9)	0.67467 (9)	0.1119 (4)
Cl4	0.68248 (17)	0.53534 (12)	0.79043 (9)	0.1696 (8)
N1	0.4862 (2)	0.24492 (17)	0.57811 (15)	0.0558 (5)
N2	0.34094 (19)	0.16803 (15)	0.66356 (12)	0.0513 (5)
C1	0.3049 (3)	0.1063 (2)	0.47620 (17)	0.0686 (8)
H1A	0.2382	0.0985	0.4309	0.082*
H1B	0.3768	0.1127	0.4545	0.082*
C2	0.3163 (3)	0.0226 (2)	0.52556 (17)	0.0606 (7)
C3	0.2208 (3)	−0.0357 (2)	0.5251 (2)	0.0721 (8)
H3	0.1468	−0.0219	0.4926	0.087*
C4	0.2322 (3)	−0.1133 (3)	0.5713 (2)	0.0788 (9)
H4	0.1670	−0.1518	0.5696	0.095*
C5	0.3412 (3)	−0.1333 (2)	0.6199 (2)	0.0726 (8)
C6	0.4370 (3)	−0.0777 (2)	0.62247 (19)	0.0680 (8)
H6	0.5105	−0.0920	0.6555	0.082*
C7	0.4249 (3)	−0.0004 (2)	0.57607 (18)	0.0639 (7)
H7	0.4907	0.0377	0.5784	0.077*
C8	0.2463 (3)	0.3566 (2)	0.5963 (2)	0.0728 (8)
H8A	0.2064	0.3988	0.5553	0.087*
H8B	0.1911	0.3434	0.6313	0.087*
C9	0.3519 (3)	0.4035 (2)	0.64484 (19)	0.0664 (8)
C10	0.3852 (3)	0.3904 (2)	0.7278 (2)	0.0735 (8)
H10	0.3389	0.3529	0.7535	0.088*
C11	0.4853 (4)	0.4318 (3)	0.7727 (2)	0.0858 (11)
H11	0.5059	0.4230	0.8282	0.103*
C12	0.5538 (4)	0.4856 (3)	0.7352 (2)	0.0943 (12)
C13	0.5227 (4)	0.5011 (3)	0.6537 (2)	0.0985 (13)
H13	0.5691	0.5394	0.6288	0.118*
C14	0.4235 (4)	0.4599 (2)	0.6093 (2)	0.0797 (9)
H14	0.4035	0.4699	0.5539	0.096*
C15	0.5562 (3)	0.2800 (2)	0.5314 (2)	0.0705 (9)
H15	0.5227	0.2934	0.4778	0.085*
C16	0.6750 (3)	0.2967 (3)	0.5597 (2)	0.0813 (10)
H16	0.7213	0.3205	0.5254	0.098*
C17	0.7262 (3)	0.2785 (3)	0.6385 (3)	0.0825 (10)
C18	0.6537 (3)	0.2412 (2)	0.6866 (2)	0.0689 (8)
H18	0.6858	0.2277	0.7404	0.083*
C19	0.5348 (2)	0.22410 (18)	0.65515 (16)	0.0516 (6)
C20	0.8561 (4)	0.2981 (5)	0.6727 (3)	0.139 (2)
H20A	0.8984	0.3037	0.6295	0.209*
H20B	0.8899	0.2492	0.7077	0.209*
H20C	0.8629	0.3540	0.7028	0.209*
C21	0.4549 (2)	0.17973 (18)	0.70150 (15)	0.0528 (6)
C22	0.4934 (3)	0.1484 (2)	0.77971 (18)	0.0733 (9)
H22	0.5725	0.1579	0.8060	0.088*
C23	0.4162 (4)	0.1035 (3)	0.81914 (19)	0.0831 (10)
C24	0.3023 (3)	0.0899 (2)	0.7781 (2)	0.0772 (9)
H24	0.2483	0.0580	0.8019	0.093*
C25	0.2669 (3)	0.1234 (2)	0.70125 (18)	0.0632 (7)
H25	0.1879	0.1147	0.6744	0.076*
C26	0.4588 (5)	0.0702 (4)	0.9050 (2)	0.138 (2)
H26A	0.4559	0.0049	0.9060	0.206*
H26B	0.4079	0.0946	0.9385	0.206*
H26C	0.5397	0.0902	0.9249	0.206*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.04228 (11)	0.06803 (14)	0.04599 (12)	0.00021 (8)	−0.00217 (8)	0.00089 (8)
Cl1	0.0438 (4)	0.1234 (8)	0.1241 (8)	−0.0074 (4)	0.0018 (4)	−0.0088 (7)
Cl2	0.0821 (6)	0.1201 (8)	0.0552 (5)	−0.0123 (5)	−0.0105 (4)	0.0282 (5)
Cl3	0.1097 (9)	0.1036 (8)	0.1256 (10)	−0.0010 (6)	0.0316 (8)	0.0320 (7)
Cl4	0.2037 (16)	0.1603 (14)	0.1127 (10)	−0.1049 (13)	−0.0418 (10)	0.0234 (9)
N1	0.0450 (12)	0.0726 (15)	0.0471 (13)	−0.0018 (10)	0.0032 (10)	0.0021 (10)
N2	0.0498 (11)	0.0597 (13)	0.0425 (11)	−0.0029 (9)	0.0052 (9)	−0.0037 (10)
C1	0.0699 (18)	0.087 (2)	0.0462 (15)	0.0005 (16)	0.0043 (13)	−0.0122 (15)
C2	0.0583 (15)	0.0721 (19)	0.0503 (15)	0.0011 (13)	0.0084 (12)	−0.0151 (13)
C3	0.0534 (17)	0.088 (2)	0.0686 (19)	−0.0050 (15)	−0.0018 (14)	−0.0151 (18)
C4	0.0645 (19)	0.085 (2)	0.086 (2)	−0.0156 (17)	0.0133 (17)	−0.012 (2)
C5	0.074 (2)	0.076 (2)	0.071 (2)	−0.0009 (16)	0.0231 (16)	−0.0028 (17)
C6	0.0580 (17)	0.082 (2)	0.0625 (18)	0.0071 (15)	0.0097 (14)	−0.0047 (16)
C7	0.0520 (15)	0.079 (2)	0.0605 (17)	−0.0022 (13)	0.0127 (13)	−0.0135 (15)
C8	0.0664 (18)	0.072 (2)	0.077 (2)	0.0131 (15)	0.0066 (16)	−0.0032 (17)
C9	0.078 (2)	0.0556 (16)	0.0646 (18)	0.0083 (14)	0.0125 (15)	−0.0035 (14)
C10	0.094 (2)	0.0649 (19)	0.0637 (19)	0.0016 (17)	0.0216 (17)	−0.0017 (15)
C11	0.123 (3)	0.074 (2)	0.0553 (18)	−0.008 (2)	0.0051 (19)	0.0007 (16)
C12	0.123 (3)	0.076 (2)	0.073 (2)	−0.032 (2)	−0.005 (2)	0.0002 (19)
C13	0.133 (4)	0.079 (2)	0.079 (2)	−0.038 (2)	0.012 (2)	0.009 (2)
C14	0.104 (3)	0.069 (2)	0.0620 (19)	−0.0090 (19)	0.0083 (18)	0.0058 (16)
C15	0.0569 (17)	0.100 (3)	0.0549 (17)	−0.0075 (15)	0.0106 (14)	0.0061 (16)
C16	0.0580 (18)	0.111 (3)	0.079 (2)	−0.0180 (18)	0.0228 (17)	−0.002 (2)
C17	0.0478 (17)	0.110 (3)	0.085 (3)	−0.0116 (16)	0.0041 (16)	−0.013 (2)
C18	0.0496 (16)	0.091 (2)	0.0591 (18)	−0.0032 (14)	−0.0051 (13)	−0.0041 (16)
C19	0.0464 (13)	0.0581 (15)	0.0456 (14)	0.0008 (11)	−0.0012 (11)	−0.0047 (11)
C20	0.054 (2)	0.222 (6)	0.133 (4)	−0.037 (3)	−0.001 (2)	−0.004 (4)
C21	0.0567 (14)	0.0535 (15)	0.0434 (13)	−0.0033 (11)	−0.0006 (11)	−0.0032 (11)
C22	0.080 (2)	0.076 (2)	0.0520 (17)	−0.0178 (16)	−0.0151 (14)	0.0107 (15)
C23	0.112 (3)	0.079 (2)	0.0510 (17)	−0.026 (2)	−0.0015 (18)	0.0113 (16)
C24	0.101 (3)	0.074 (2)	0.0589 (18)	−0.0274 (18)	0.0211 (18)	−0.0006 (16)
C25	0.0643 (17)	0.0681 (18)	0.0575 (17)	−0.0124 (14)	0.0131 (13)	−0.0064 (14)
C26	0.184 (5)	0.145 (5)	0.066 (2)	−0.062 (4)	−0.016 (3)	0.040 (3)

Geometric parameters (Å, º) top

Sn1—C1	2.151 (3)	C10—H10	0.9300
Sn1—C8	2.166 (3)	C11—C12	1.357 (5)
Sn1—N2	2.313 (2)	C11—H11	0.9300
Sn1—N1	2.337 (2)	C12—C13	1.371 (5)
Sn1—Cl1	2.4970 (9)	C13—C14	1.363 (5)
Sn1—Cl2	2.5293 (8)	C13—H13	0.9300
Cl3—C5	1.731 (4)	C14—H14	0.9300
Cl4—C12	1.730 (4)	C15—C16	1.363 (5)
N1—C19	1.343 (4)	C15—H15	0.9300
N1—C15	1.337 (4)	C16—C17	1.366 (5)
N2—C25	1.331 (4)	C16—H16	0.9300
N2—C21	1.336 (3)	C17—C18	1.388 (5)
C1—C2	1.476 (5)	C17—C20	1.502 (5)
C1—H1A	0.9700	C18—C19	1.374 (4)
C1—H1B	0.9700	C18—H18	0.9300
C2—C3	1.384 (4)	C19—C21	1.472 (4)
C2—C7	1.394 (4)	C20—H20A	0.9600
C3—C4	1.372 (5)	C20—H20B	0.9600
C3—H3	0.9300	C20—H20C	0.9600
C4—C5	1.374 (5)	C21—C22	1.384 (4)
C4—H4	0.9300	C22—C23	1.378 (5)
C5—C6	1.358 (5)	C22—H22	0.9300
C6—C7	1.371 (5)	C23—C24	1.356 (5)
C6—H6	0.9300	C23—C26	1.515 (5)
C7—H7	0.9300	C24—C25	1.371 (4)
C8—C9	1.480 (5)	C24—H24	0.9300
C8—H8A	0.9700	C25—H25	0.9300
C8—H8B	0.9700	C26—H26A	0.9600
C9—C10	1.391 (5)	C26—H26B	0.9600
C9—C14	1.385 (5)	C26—H26C	0.9600
C10—C11	1.375 (5)

C1—Sn1—C8	178.42 (12)	C9—C10—H10	119.4
C1—Sn1—N2	93.06 (10)	C12—C11—C10	119.4 (3)
C8—Sn1—N2	87.58 (11)	C12—C11—H11	120.3
C1—Sn1—N1	88.99 (11)	C10—C11—H11	120.3
C8—Sn1—N1	92.59 (11)	C11—C12—C13	120.9 (4)
N2—Sn1—N1	69.92 (8)	C11—C12—Cl4	119.9 (3)
C1—Sn1—Cl1	90.48 (9)	C13—C12—Cl4	119.2 (3)
C8—Sn1—Cl1	88.01 (9)	C14—C13—C12	119.5 (4)
N2—Sn1—Cl1	95.66 (6)	C14—C13—H13	120.2
N1—Sn1—Cl1	165.52 (7)	C12—C13—H13	120.2
C1—Sn1—Cl2	88.68 (9)	C13—C14—C9	121.5 (3)
C8—Sn1—Cl2	91.21 (10)	C13—C14—H14	119.2
N2—Sn1—Cl2	160.01 (6)	C9—C14—H14	119.2
N1—Sn1—Cl2	90.22 (6)	N1—C15—C16	122.2 (3)
Cl1—Sn1—Cl2	104.24 (4)	N1—C15—H15	118.9
C19—N1—C15	119.0 (3)	C16—C15—H15	118.9
C19—N1—Sn1	117.50 (18)	C15—C16—C17	120.1 (3)
C15—N1—Sn1	123.2 (2)	C15—C16—H16	120.0
C25—N2—C21	118.9 (2)	C17—C16—H16	120.0
C25—N2—Sn1	122.54 (19)	C16—C17—C18	117.6 (3)
C21—N2—Sn1	118.53 (17)	C16—C17—C20	121.8 (4)
C2—C1—Sn1	116.38 (19)	C18—C17—C20	120.5 (4)
C2—C1—H1A	108.2	C19—C18—C17	120.3 (3)
Sn1—C1—H1A	108.2	C19—C18—H18	119.9
C2—C1—H1B	108.2	C17—C18—H18	119.9
Sn1—C1—H1B	108.2	N1—C19—C18	120.8 (3)
H1A—C1—H1B	107.3	N1—C19—C21	116.2 (2)
C3—C2—C7	116.8 (3)	C18—C19—C21	123.0 (3)
C3—C2—C1	122.4 (3)	C17—C20—H20A	109.5
C7—C2—C1	120.8 (3)	C17—C20—H20B	109.5
C4—C3—C2	122.0 (3)	H20A—C20—H20B	109.5
C4—C3—H3	119.0	C17—C20—H20C	109.5
C2—C3—H3	119.0	H20A—C20—H20C	109.5
C3—C4—C5	119.1 (3)	H20B—C20—H20C	109.5
C3—C4—H4	120.4	N2—C21—C22	120.1 (3)
C5—C4—H4	120.4	N2—C21—C19	116.6 (2)
C6—C5—C4	120.9 (3)	C22—C21—C19	123.2 (3)
C6—C5—Cl3	120.0 (3)	C23—C22—C21	120.9 (3)
C4—C5—Cl3	119.1 (3)	C23—C22—H22	119.5
C5—C6—C7	119.6 (3)	C21—C22—H22	119.5
C5—C6—H6	120.2	C24—C23—C22	117.5 (3)
C7—C6—H6	120.2	C24—C23—C26	121.9 (4)
C6—C7—C2	121.6 (3)	C22—C23—C26	120.6 (4)
C6—C7—H7	119.2	C23—C24—C25	119.8 (3)
C2—C7—H7	119.2	C23—C24—H24	120.1
C9—C8—Sn1	117.3 (2)	C25—C24—H24	120.1
C9—C8—H8A	108.0	N2—C25—C24	122.7 (3)
Sn1—C8—H8A	108.0	N2—C25—H25	118.7
C9—C8—H8B	108.0	C24—C25—H25	118.7
Sn1—C8—H8B	108.0	C23—C26—H26A	109.5
H8A—C8—H8B	107.2	C23—C26—H26B	109.5
C10—C9—C14	117.3 (3)	H26A—C26—H26B	109.5
C10—C9—C8	121.2 (3)	C23—C26—H26C	109.5
C14—C9—C8	121.4 (3)	H26A—C26—H26C	109.5
C11—C10—C9	121.3 (3)	H26B—C26—H26C	109.5
C11—C10—H10	119.4

C1—Sn1—N1—C15	82.9 (3)	Sn1—C8—C9—C10	−95.9 (3)
N2—Sn1—N1—C15	176.5 (3)	C14—C9—C10—C11	−0.1 (5)
Cl1—Sn1—N1—C15	170.9 (2)	C8—C9—C10—C11	178.0 (3)
Cl2—Sn1—N1—C15	−5.8 (3)	C9—C10—C11—C12	−0.8 (6)
C1—Sn1—N1—C19	−103.4 (2)	C10—C11—C12—C13	1.7 (7)
C8—Sn1—N1—C19	76.7 (2)	C10—C11—C12—Cl4	−178.0 (3)
N2—Sn1—N1—C19	−9.79 (19)	C11—C12—C13—C14	−1.8 (7)
Cl1—Sn1—N1—C19	−15.4 (4)	Cl4—C12—C13—C14	178.0 (4)
Cl2—Sn1—N1—C19	167.9 (2)	C12—C13—C14—C9	0.9 (7)
C1—Sn1—N2—C25	−86.3 (2)	C10—C9—C14—C13	0.0 (6)
C8—Sn1—N2—C25	92.2 (2)	C8—C9—C14—C13	−178.1 (4)
N1—Sn1—N2—C25	−174.1 (2)	C19—N1—C15—C16	−1.1 (5)
Cl1—Sn1—N2—C25	4.5 (2)	Sn1—N1—C15—C16	172.5 (3)
Cl2—Sn1—N2—C25	179.13 (18)	N1—C15—C16—C17	−0.7 (6)
C1—Sn1—N2—C21	96.2 (2)	C15—C16—C17—C18	1.4 (6)
C8—Sn1—N2—C21	−85.3 (2)	C15—C16—C17—C20	−178.4 (4)
N1—Sn1—N2—C21	8.36 (19)	C16—C17—C18—C19	−0.3 (6)
Cl1—Sn1—N2—C21	−173.05 (19)	C20—C17—C18—C19	179.5 (4)
Cl2—Sn1—N2—C21	1.6 (3)	C15—N1—C19—C18	2.2 (4)
C8—Sn1—C1—C2	−97 (5)	Sn1—N1—C19—C18	−171.8 (2)
N2—Sn1—C1—C2	16.6 (2)	C15—N1—C19—C21	−175.8 (3)
N1—Sn1—C1—C2	86.5 (2)	Sn1—N1—C19—C21	10.3 (3)
Cl1—Sn1—C1—C2	−79.0 (2)	C17—C18—C19—N1	−1.5 (5)
Cl2—Sn1—C1—C2	176.7 (2)	C17—C18—C19—C21	176.3 (3)
Sn1—C1—C2—C3	97.9 (3)	C25—N2—C21—C22	−2.2 (4)
Sn1—C1—C2—C7	−81.2 (3)	Sn1—N2—C21—C22	175.5 (2)
C7—C2—C3—C4	−0.8 (5)	C25—N2—C21—C19	176.1 (2)
C1—C2—C3—C4	−179.9 (3)	Sn1—N2—C21—C19	−6.3 (3)
C2—C3—C4—C5	0.6 (5)	N1—C19—C21—N2	−2.7 (4)
C3—C4—C5—C6	−0.3 (5)	C18—C19—C21—N2	179.4 (3)
C3—C4—C5—Cl3	−177.1 (3)	N1—C19—C21—C22	175.5 (3)
C4—C5—C6—C7	0.3 (5)	C18—C19—C21—C22	−2.4 (5)
Cl3—C5—C6—C7	177.0 (2)	N2—C21—C22—C23	1.2 (5)
C5—C6—C7—C2	−0.5 (5)	C19—C21—C22—C23	−176.9 (3)
C3—C2—C7—C6	0.7 (4)	C21—C22—C23—C24	1.0 (6)
C1—C2—C7—C6	179.9 (3)	C21—C22—C23—C26	−179.4 (4)
N2—Sn1—C8—C9	65.4 (3)	C22—C23—C24—C25	−2.2 (6)
N1—Sn1—C8—C9	−4.4 (3)	C26—C23—C24—C25	178.2 (4)
Cl1—Sn1—C8—C9	161.1 (3)	C21—N2—C25—C24	0.9 (4)
Cl2—Sn1—C8—C9	−94.6 (3)	Sn1—N2—C25—C24	−176.6 (2)
Sn1—C8—C9—C14	82.1 (4)	C23—C24—C25—N2	1.4 (5)

Experimental details

Crystal data
Chemical formula	[Sn(C₇H₆Cl)₂Cl₂(C₁₂H₁₂N₂)]
M_r	624.96
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.4035 (6), 14.6804 (8), 16.9270 (9)
β (°)	101.9182 (9)
V (Å³)	2772.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.32
Crystal size (mm)	0.30 × 0.28 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.692, 0.778
No. of measured, independent and observed [I > 2σ(I)] reflections	15766, 6263, 4883
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.095, 1.00
No. of reflections	6263
No. of parameters	300
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.49

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

Acknowledgements

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

References

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