Dichloridobis(4-chloro­benzyl-κC)(1,10-phenanthroline-κ2N,N′)tin(IV)

Tan, C.L.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536809019795

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m717

doi:10.1107/S1600536809019795

Open

access

Dichloridobis(4-chlorobenzyl-κC)(1,10-phenanthroline-κ²N,N′)tin(IV)

Chui Lian Tan,^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 21 May 2009; accepted 25 May 2009; online 6 June 2009)

In the crystal structure of the title compound, [Sn(C₇H₆Cl)₂Cl₂(C₁₂H₈N₂)], the Sn^IV atom is chelated by the N-heterocycle and the metal atom exists in a trans-C₂SnCl₂N₂ distorted octahedral coordination environment.

Related literature

Several diorganotin dichloride adducts of 2,2′-bipyridine have been reported. For the diethyltin dichloride, dibutyltin dichoride and dibenzyltin dichloride adducts; see Chadha et al. (1980 ); Gill et al.(1999 ); Tiekink et al. (2000 ). For the structure of di(4-chlorobenzyltin) dichloride, see: Kuang & Feng (2000 ). For the direct synthesis of di(chlorobenzyl)tin dichlorides, see: Sisido et al. (1961 ).

Experimental

Crystal data

[Sn(C₇H₆Cl)₂Cl₂(C₁₂H₈N₂)]
M_r = 620.93
Monoclinic, P 2₁ /c
a = 8.9252 (1) Å
b = 17.9987 (3) Å
c = 15.6862 (3) Å
β = 98.686 (1)°
V = 2490.96 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.47 mm⁻¹
T = 119 K
0.40 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.590, T_max = 0.867
16905 measured reflections
5681 independent reflections
4826 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.062
S = 1.05
5681 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—C1	2.160 (2)
Sn1—C8	2.162 (2)
Sn1—N1	2.3712 (18)
Sn1—N2	2.3515 (18)
Sn1—Cl3	2.5287 (6)
Sn1—Cl4	2.4973 (6)

C1—Sn1—C8	172.84 (8)

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536809019795/xu2530sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019795/xu2530Isup2.hkl

checkCIF report

Related literature top

Several diorganotin dichloride adducts of 2,2'-bipyridine have been reported. For the diethyltin dichloride, dibutyltin dichoride and dibenzyltin dichloride adducts; see Chadha et al. (1980); Gill et al.(1999); Tiekink et al. (2000). For the structure of di(4-chlorobenzyltin) dichloride, see: Kuang & Feng (2000). For the direct synthesis of di(chlorobenzyl)tin dichlorides, see: Sisido et al. (1961).

Experimental top

Di(p-chlorobenzyl)tin dichloride was synthesized by the reaction of p-chlorobenzyl chloride and metallic tin (Sisido et al., 1961). The reactant (0.5 g, 1.1 mmol) and 1,10-phenanthroline (0.2 g, 1.1 mmol) were heated in chloroform (50 ml) for 1 hour. Faint-yellow crystals separated from the cool solution after a day.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. The molecular structure of the title compound with 70% displacement probability ellipsoids. Hydrogen atoms are drawn as spheres of arbitrary radius.

Dichloridobis(4-chlorobenzyl-κC)(1,10-phenanthroline- κ²N,N')tin(IV) top

Crystal data top

[Sn(C₇H₆Cl)₂Cl₂(C₁₂H₈N₂)]	F(000) = 1232
M_r = 620.93	D_x = 1.656 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8381 reflections
a = 8.9252 (1) Å	θ = 2.3–28.2°
b = 17.9987 (3) Å	µ = 1.47 mm⁻¹
c = 15.6862 (3) Å	T = 119 K
β = 98.686 (1)°	Prism, yellow
V = 2490.96 (7) Å³	0.40 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	5681 independent reflections
Radiation source: fine-focus sealed tube	4826 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.590, T_max = 0.867	k = −22→23
16905 measured reflections	l = −20→20

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.062	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0286P)² + 1.4291P] where P = (F_o² + 2F_c²)/3
5681 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[Sn(C₇H₆Cl)₂Cl₂(C₁₂H₈N₂)]	V = 2490.96 (7) Å³
M_r = 620.93	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9252 (1) Å	µ = 1.47 mm⁻¹
b = 17.9987 (3) Å	T = 119 K
c = 15.6862 (3) Å	0.40 × 0.10 × 0.10 mm
β = 98.686 (1)°

Data collection top

Bruker SMART APEX diffractometer	5681 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4826 reflections with I > 2σ(I)
T_min = 0.590, T_max = 0.867	R_int = 0.021
16905 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.062	H-atom parameters constrained
S = 1.05	Δρ_max = 0.53 e Å⁻³
5681 reflections	Δρ_min = −0.44 e Å⁻³
298 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.668417 (16)	0.554696 (8)	0.795225 (9)	0.02121 (5)
Cl1	0.84702 (8)	0.57955 (4)	0.35794 (4)	0.04106 (15)
Cl2	1.35725 (11)	0.75339 (6)	0.97376 (6)	0.0765 (3)
Cl3	0.42667 (7)	0.52254 (3)	0.85279 (4)	0.03635 (14)
Cl4	0.82575 (7)	0.43941 (3)	0.81282 (4)	0.03295 (13)
N1	0.5902 (2)	0.67771 (10)	0.75699 (12)	0.0231 (4)
N2	0.8592 (2)	0.61534 (10)	0.73338 (12)	0.0232 (4)
C1	0.7565 (3)	0.59581 (14)	0.92228 (15)	0.0302 (5)
H1A	0.6811	0.6304	0.9405	0.036*
H1B	0.7663	0.5533	0.9628	0.036*
C2	0.9049 (3)	0.63463 (13)	0.93108 (14)	0.0291 (5)
C3	1.0409 (3)	0.59536 (13)	0.94752 (15)	0.0313 (5)
H3A	1.0382	0.5427	0.9503	0.038*
C4	1.1800 (3)	0.63119 (16)	0.95997 (17)	0.0399 (6)
H4A	1.2716	0.6037	0.9725	0.048*
C5	1.1823 (4)	0.70741 (17)	0.95385 (17)	0.0444 (7)
C6	1.0518 (4)	0.74826 (15)	0.93470 (18)	0.0499 (8)
H6A	1.0560	0.8007	0.9292	0.060*
C7	0.9140 (3)	0.71175 (14)	0.92356 (16)	0.0399 (6)
H7A	0.8232	0.7398	0.9105	0.048*
C8	0.5528 (2)	0.51792 (13)	0.67136 (15)	0.0259 (5)
H8A	0.5366	0.4636	0.6746	0.031*
H8B	0.4516	0.5416	0.6615	0.031*
C9	0.6284 (2)	0.53300 (12)	0.59490 (14)	0.0236 (4)
C10	0.7343 (3)	0.48429 (13)	0.56968 (15)	0.0281 (5)
H10A	0.7604	0.4406	0.6025	0.034*
C11	0.8025 (3)	0.49820 (13)	0.49766 (15)	0.0294 (5)
H11A	0.8738	0.4641	0.4808	0.035*
C12	0.7655 (3)	0.56232 (13)	0.45046 (15)	0.0290 (5)
C13	0.6620 (3)	0.61251 (13)	0.47410 (15)	0.0301 (5)
H13A	0.6378	0.6566	0.4416	0.036*
C14	0.5942 (3)	0.59752 (13)	0.54598 (15)	0.0281 (5)
H14A	0.5228	0.6318	0.5625	0.034*
C15	0.6868 (2)	0.71888 (11)	0.71740 (14)	0.0221 (4)
C16	0.4601 (3)	0.70774 (13)	0.77128 (15)	0.0277 (5)
H16A	0.3933	0.6790	0.7998	0.033*
C17	0.4182 (3)	0.78056 (13)	0.74554 (17)	0.0334 (5)
H17A	0.3249	0.8007	0.7569	0.040*
C18	0.5130 (3)	0.82184 (13)	0.70422 (16)	0.0325 (5)
H18A	0.4846	0.8707	0.6852	0.039*
C19	0.6528 (3)	0.79239 (12)	0.68953 (15)	0.0281 (5)
C20	0.7614 (3)	0.83310 (13)	0.64909 (15)	0.0346 (6)
H20A	0.7388	0.8825	0.6299	0.041*
C21	0.8942 (3)	0.80256 (14)	0.63798 (15)	0.0337 (6)
H21A	0.9643	0.8308	0.6114	0.040*
C22	0.9325 (3)	0.72786 (13)	0.66552 (14)	0.0282 (5)
C23	1.0714 (3)	0.69379 (16)	0.65643 (16)	0.0348 (6)
H23A	1.1443	0.7199	0.6297	0.042*
C24	1.1010 (3)	0.62301 (15)	0.68614 (16)	0.0356 (6)
H24A	1.1948	0.5998	0.6810	0.043*
C25	0.9913 (3)	0.58531 (14)	0.72420 (15)	0.0288 (5)
H25A	1.0124	0.5361	0.7443	0.035*
C26	0.8288 (2)	0.68613 (12)	0.70487 (14)	0.0231 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.02126 (8)	0.01781 (8)	0.02478 (8)	0.00048 (6)	0.00414 (6)	−0.00034 (6)
Cl1	0.0462 (4)	0.0487 (4)	0.0299 (3)	−0.0001 (3)	0.0111 (3)	0.0010 (3)
Cl2	0.0833 (6)	0.0975 (7)	0.0515 (5)	−0.0638 (6)	0.0192 (5)	−0.0244 (5)
Cl3	0.0361 (3)	0.0285 (3)	0.0493 (4)	−0.0040 (2)	0.0220 (3)	−0.0024 (3)
Cl4	0.0322 (3)	0.0230 (3)	0.0424 (3)	0.0073 (2)	0.0017 (3)	0.0020 (2)
N1	0.0221 (9)	0.0201 (9)	0.0271 (10)	−0.0018 (7)	0.0033 (8)	−0.0027 (7)
N2	0.0204 (9)	0.0261 (10)	0.0226 (9)	−0.0026 (7)	0.0019 (7)	−0.0039 (7)
C1	0.0345 (13)	0.0315 (12)	0.0244 (11)	0.0055 (10)	0.0041 (10)	−0.0019 (10)
C2	0.0420 (14)	0.0268 (12)	0.0179 (11)	−0.0005 (10)	0.0033 (10)	−0.0027 (9)
C3	0.0388 (13)	0.0265 (12)	0.0287 (12)	−0.0032 (10)	0.0053 (10)	−0.0051 (10)
C4	0.0391 (14)	0.0490 (16)	0.0327 (14)	−0.0081 (12)	0.0083 (12)	−0.0129 (12)
C5	0.0597 (19)	0.0497 (17)	0.0246 (13)	−0.0293 (15)	0.0090 (13)	−0.0113 (12)
C6	0.087 (2)	0.0287 (14)	0.0304 (14)	−0.0172 (15)	−0.0030 (15)	−0.0025 (11)
C7	0.0597 (18)	0.0270 (13)	0.0296 (13)	0.0023 (12)	−0.0038 (12)	−0.0051 (10)
C8	0.0195 (10)	0.0280 (12)	0.0296 (12)	−0.0026 (9)	0.0018 (9)	−0.0041 (9)
C9	0.0186 (10)	0.0264 (11)	0.0237 (11)	−0.0024 (8)	−0.0037 (9)	−0.0047 (9)
C10	0.0253 (11)	0.0274 (12)	0.0298 (12)	0.0006 (9)	−0.0015 (10)	−0.0026 (9)
C11	0.0244 (11)	0.0325 (12)	0.0304 (12)	0.0031 (9)	0.0015 (10)	−0.0047 (10)
C12	0.0266 (11)	0.0369 (13)	0.0227 (11)	−0.0023 (10)	0.0004 (9)	−0.0024 (10)
C13	0.0303 (12)	0.0295 (12)	0.0275 (12)	0.0033 (10)	−0.0052 (10)	0.0006 (10)
C14	0.0263 (11)	0.0272 (12)	0.0290 (12)	0.0049 (9)	−0.0019 (9)	−0.0043 (9)
C15	0.0269 (11)	0.0198 (10)	0.0186 (10)	−0.0044 (8)	0.0004 (8)	−0.0030 (8)
C16	0.0256 (11)	0.0242 (11)	0.0336 (13)	0.0000 (9)	0.0053 (10)	−0.0026 (9)
C17	0.0349 (13)	0.0254 (12)	0.0396 (14)	0.0061 (10)	0.0042 (11)	−0.0042 (10)
C18	0.0448 (14)	0.0188 (11)	0.0326 (13)	0.0041 (10)	0.0016 (11)	0.0003 (9)
C19	0.0387 (13)	0.0200 (11)	0.0247 (11)	−0.0039 (9)	0.0018 (10)	−0.0028 (9)
C20	0.0540 (16)	0.0229 (12)	0.0271 (12)	−0.0084 (11)	0.0072 (11)	0.0010 (9)
C21	0.0447 (15)	0.0321 (13)	0.0248 (12)	−0.0179 (11)	0.0072 (11)	−0.0028 (10)
C22	0.0311 (12)	0.0347 (13)	0.0186 (11)	−0.0118 (10)	0.0030 (9)	−0.0041 (9)
C23	0.0262 (12)	0.0531 (16)	0.0260 (12)	−0.0147 (11)	0.0066 (10)	−0.0045 (11)
C24	0.0233 (11)	0.0501 (16)	0.0341 (13)	−0.0029 (11)	0.0070 (10)	−0.0070 (12)
C25	0.0233 (11)	0.0351 (12)	0.0280 (12)	0.0001 (10)	0.0036 (9)	−0.0055 (10)
C26	0.0250 (11)	0.0245 (11)	0.0190 (10)	−0.0059 (9)	0.0011 (8)	−0.0045 (8)

Geometric parameters (Å, º) top

Sn1—C1	2.160 (2)	C9—C14	1.400 (3)
Sn1—C8	2.162 (2)	C10—C11	1.385 (3)
Sn1—N1	2.3712 (18)	C10—H10A	0.9500
Sn1—N2	2.3515 (18)	C11—C12	1.384 (3)
Sn1—Cl3	2.5287 (6)	C11—H11A	0.9500
Sn1—Cl4	2.4973 (6)	C12—C13	1.382 (3)
Cl1—C12	1.747 (2)	C13—C14	1.385 (3)
Cl2—C5	1.753 (3)	C13—H13A	0.9500
N1—C16	1.330 (3)	C14—H14A	0.9500
N1—C15	1.356 (3)	C15—C19	1.412 (3)
N2—C25	1.325 (3)	C15—C26	1.438 (3)
N2—C26	1.364 (3)	C16—C17	1.405 (3)
C1—C2	1.486 (3)	C16—H16A	0.9500
C1—H1A	0.9900	C17—C18	1.361 (4)
C1—H1B	0.9900	C17—H17A	0.9500
C2—C3	1.394 (3)	C18—C19	1.406 (3)
C2—C7	1.397 (3)	C18—H18A	0.9500
C3—C4	1.386 (4)	C19—C20	1.437 (3)
C3—H3A	0.9500	C20—C21	1.342 (4)
C4—C5	1.376 (4)	C20—H20A	0.9500
C4—H4A	0.9500	C21—C22	1.437 (4)
C5—C6	1.372 (4)	C21—H21A	0.9500
C6—C7	1.382 (4)	C22—C26	1.405 (3)
C6—H6A	0.9500	C22—C23	1.410 (3)
C7—H7A	0.9500	C23—C24	1.368 (4)
C8—C9	1.487 (3)	C23—H23A	0.9500
C8—H8A	0.9900	C24—C25	1.397 (3)
C8—H8B	0.9900	C24—H24A	0.9500
C9—C10	1.390 (3)	C25—H25A	0.9500

C1—Sn1—C8	172.84 (8)	C14—C9—C8	120.4 (2)
C8—Sn1—N2	92.78 (7)	C11—C10—C9	121.3 (2)
C1—Sn1—N2	92.08 (8)	C11—C10—H10A	119.3
C8—Sn1—N1	88.64 (8)	C9—C10—H10A	119.3
C1—Sn1—N1	88.03 (8)	C10—C11—C12	119.3 (2)
N2—Sn1—N1	70.49 (6)	C10—C11—H11A	120.4
C8—Sn1—Cl4	91.67 (6)	C12—C11—H11A	120.4
C1—Sn1—Cl4	93.58 (7)	C13—C12—C11	121.1 (2)
N2—Sn1—Cl4	90.07 (5)	C13—C12—Cl1	119.07 (19)
N1—Sn1—Cl4	160.55 (5)	C11—C12—Cl1	119.81 (18)
C8—Sn1—Cl3	86.19 (6)	C14—C13—C12	118.9 (2)
C1—Sn1—Cl3	87.72 (7)	C14—C13—H13A	120.6
N2—Sn1—Cl3	164.47 (5)	C12—C13—H13A	120.6
N1—Sn1—Cl3	93.99 (5)	C13—C14—C9	121.5 (2)
Cl4—Sn1—Cl3	105.44 (2)	C13—C14—H14A	119.3
C16—N1—C15	119.11 (19)	C9—C14—H14A	119.3
C16—N1—Sn1	124.61 (15)	N1—C15—C19	122.1 (2)
C15—N1—Sn1	116.28 (14)	N1—C15—C26	118.23 (19)
C25—N2—C26	118.79 (19)	C19—C15—C26	119.6 (2)
C25—N2—Sn1	124.56 (16)	N1—C16—C17	122.1 (2)
C26—N2—Sn1	116.65 (14)	N1—C16—H16A	118.9
C2—C1—Sn1	116.24 (15)	C17—C16—H16A	118.9
C2—C1—H1A	108.2	C18—C17—C16	119.3 (2)
Sn1—C1—H1A	108.2	C18—C17—H17A	120.4
C2—C1—H1B	108.2	C16—C17—H17A	120.4
Sn1—C1—H1B	108.2	C17—C18—C19	120.2 (2)
H1A—C1—H1B	107.4	C17—C18—H18A	119.9
C3—C2—C7	117.4 (2)	C19—C18—H18A	119.9
C3—C2—C1	121.2 (2)	C18—C19—C15	117.2 (2)
C7—C2—C1	121.4 (2)	C18—C19—C20	123.7 (2)
C4—C3—C2	121.7 (2)	C15—C19—C20	119.1 (2)
C4—C3—H3A	119.1	C21—C20—C19	121.1 (2)
C2—C3—H3A	119.1	C21—C20—H20A	119.4
C5—C4—C3	118.5 (3)	C19—C20—H20A	119.4
C5—C4—H4A	120.8	C20—C21—C22	121.2 (2)
C3—C4—H4A	120.8	C20—C21—H21A	119.4
C6—C5—C4	121.9 (3)	C22—C21—H21A	119.4
C6—C5—Cl2	119.3 (2)	C26—C22—C23	117.4 (2)
C4—C5—Cl2	118.7 (3)	C26—C22—C21	119.3 (2)
C5—C6—C7	118.9 (3)	C23—C22—C21	123.3 (2)
C5—C6—H6A	120.6	C24—C23—C22	119.9 (2)
C7—C6—H6A	120.6	C24—C23—H23A	120.1
C6—C7—C2	121.6 (3)	C22—C23—H23A	120.1
C6—C7—H7A	119.2	C23—C24—C25	119.1 (2)
C2—C7—H7A	119.2	C23—C24—H24A	120.5
C9—C8—Sn1	117.12 (14)	C25—C24—H24A	120.5
C9—C8—H8A	108.0	N2—C25—C24	122.7 (2)
Sn1—C8—H8A	108.0	N2—C25—H25A	118.6
C9—C8—H8B	108.0	C24—C25—H25A	118.6
Sn1—C8—H8B	108.0	N2—C26—C22	122.1 (2)
H8A—C8—H8B	107.3	N2—C26—C15	118.27 (19)
C10—C9—C14	118.0 (2)	C22—C26—C15	119.6 (2)
C10—C9—C8	121.7 (2)

C8—Sn1—N1—C16	88.53 (19)	C10—C11—C12—C13	0.0 (4)
C1—Sn1—N1—C16	−85.14 (19)	C10—C11—C12—Cl1	−178.41 (18)
N2—Sn1—N1—C16	−178.0 (2)	C11—C12—C13—C14	−0.4 (3)
Cl4—Sn1—N1—C16	179.68 (13)	Cl1—C12—C13—C14	178.03 (18)
Cl3—Sn1—N1—C16	2.44 (18)	C12—C13—C14—C9	0.1 (3)
C8—Sn1—N1—C15	−91.05 (16)	C10—C9—C14—C13	0.6 (3)
C1—Sn1—N1—C15	95.29 (16)	C8—C9—C14—C13	−179.4 (2)
N2—Sn1—N1—C15	2.38 (14)	C16—N1—C15—C19	−1.0 (3)
Cl4—Sn1—N1—C15	0.1 (3)	Sn1—N1—C15—C19	178.60 (16)
Cl3—Sn1—N1—C15	−177.13 (15)	C16—N1—C15—C26	178.2 (2)
C8—Sn1—N2—C25	−94.31 (18)	Sn1—N1—C15—C26	−2.2 (2)
C1—Sn1—N2—C25	90.94 (18)	C15—N1—C16—C17	0.9 (3)
N1—Sn1—N2—C25	178.12 (19)	Sn1—N1—C16—C17	−178.64 (17)
Cl4—Sn1—N2—C25	−2.64 (17)	N1—C16—C17—C18	0.4 (4)
Cl3—Sn1—N2—C25	179.92 (14)	C16—C17—C18—C19	−1.6 (4)
C8—Sn1—N2—C26	85.20 (16)	C17—C18—C19—C15	1.5 (3)
C1—Sn1—N2—C26	−89.54 (16)	C17—C18—C19—C20	−177.8 (2)
N1—Sn1—N2—C26	−2.37 (14)	N1—C15—C19—C18	−0.2 (3)
Cl4—Sn1—N2—C26	176.87 (15)	C26—C15—C19—C18	−179.4 (2)
Cl3—Sn1—N2—C26	−0.6 (3)	N1—C15—C19—C20	179.1 (2)
N2—Sn1—C1—C2	−8.28 (18)	C26—C15—C19—C20	0.0 (3)
N1—Sn1—C1—C2	−78.67 (18)	C18—C19—C20—C21	178.9 (2)
Cl4—Sn1—C1—C2	81.92 (17)	C15—C19—C20—C21	−0.4 (4)
Cl3—Sn1—C1—C2	−172.74 (18)	C19—C20—C21—C22	0.4 (4)
Sn1—C1—C2—C3	−86.5 (2)	C20—C21—C22—C26	0.0 (3)
Sn1—C1—C2—C7	93.7 (2)	C20—C21—C22—C23	−179.0 (2)
C7—C2—C3—C4	2.9 (4)	C26—C22—C23—C24	−0.5 (3)
C1—C2—C3—C4	−176.9 (2)	C21—C22—C23—C24	178.4 (2)
C2—C3—C4—C5	−1.5 (4)	C22—C23—C24—C25	0.8 (4)
C3—C4—C5—C6	−0.9 (4)	C26—N2—C25—C24	−0.3 (3)
C3—C4—C5—Cl2	177.49 (19)	Sn1—N2—C25—C24	179.23 (17)
C4—C5—C6—C7	1.8 (4)	C23—C24—C25—N2	−0.4 (4)
Cl2—C5—C6—C7	−176.7 (2)	C25—N2—C26—C22	0.5 (3)
C5—C6—C7—C2	−0.2 (4)	Sn1—N2—C26—C22	−179.00 (16)
C3—C2—C7—C6	−2.1 (4)	C25—N2—C26—C15	−178.26 (19)
C1—C2—C7—C6	177.7 (2)	Sn1—N2—C26—C15	2.2 (2)
N2—Sn1—C8—C9	5.87 (17)	C23—C22—C26—N2	−0.1 (3)
N1—Sn1—C8—C9	76.26 (17)	C21—C22—C26—N2	−179.2 (2)
Cl4—Sn1—C8—C9	−84.29 (17)	C23—C22—C26—C15	178.7 (2)
Cl3—Sn1—C8—C9	170.35 (17)	C21—C22—C26—C15	−0.4 (3)
Sn1—C8—C9—C10	86.7 (2)	N1—C15—C26—N2	0.0 (3)
Sn1—C8—C9—C14	−93.2 (2)	C19—C15—C26—N2	179.24 (19)
C14—C9—C10—C11	−1.0 (3)	N1—C15—C26—C22	−178.8 (2)
C8—C9—C10—C11	179.0 (2)	C19—C15—C26—C22	0.4 (3)
C9—C10—C11—C12	0.7 (3)

Experimental details

Crystal data
Chemical formula	[Sn(C₇H₆Cl)₂Cl₂(C₁₂H₈N₂)]
M_r	620.93
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	119
a, b, c (Å)	8.9252 (1), 17.9987 (3), 15.6862 (3)
β (°)	98.686 (1)
V (Å³)	2490.96 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.47
Crystal size (mm)	0.40 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.590, 0.867
No. of measured, independent and observed [I > 2σ(I)] reflections	16905, 5681, 4826
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.062, 1.05
No. of reflections	5681
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.44

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected geometric parameters (Å, º) top

Sn1—C1	2.160 (2)	Sn1—N2	2.3515 (18)
Sn1—C8	2.162 (2)	Sn1—Cl3	2.5287 (6)
Sn1—N1	2.3712 (18)	Sn1—Cl4	2.4973 (6)

C1—Sn1—C8	172.84 (8)

Acknowledgements

We thank the University of Malaya (RG020/09AFR) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chadha, S. L., Harrison, P. G. & Molloy, K. C. (1980). J. Organomet. Chem. 202, 247–256. CSD CrossRef CAS Web of Science Google Scholar
Gill, J., Parge, H., Cardin, C. J., Tsiamis, C. & Kavounis, C. (1999). Acta Cryst. C55, 875–876. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Kuang, D.-Z. & Feng, Y.-L. (2000). Chin. J. Inorg. Chem. 16, 603–606. CAS 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
Sisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc. 83, 538–541. CrossRef Web of Science Google Scholar
Tiekink, E. R. T., Hall, V. J., Buntine, M. A. & Hook, J. (2000). Z. Kristallogr. 215, 23–33. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar