[N′-(5-Chloro-2-oxidobenzyl­idene-κO)-3-hydr­oxy-2-naphthohydrazidato-κ2N′,O2]diphenyl­tin(IV)

Lee, S.M.; Lo, K.M.; Ali, H.M.; Ng, S.W.

doi:10.1107/S1600536809050107

metal-organic compounds

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Volume 65| Part 12| December 2009| Page m1689

doi:10.1107/S1600536809050107

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[N′-(5-Chloro-2-oxidobenzylidene-κO)-3-hydroxy-2-naphthohydrazidato-κ²N′,O²]diphenyltin(IV)

See Mun Lee,^a Kong Mun Lo,^a Hapipah Mohd Ali ^a and Seik Weng Ng ^a ^*

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

(Received 20 November 2009; accepted 21 November 2009; online 28 November 2009)

The Sn^IV atom in the title compound, [Sn(C₆H₅)₂(C₁₈H₁₁ClN₂O₃)], is O,N,O′-chelated by the deprotonated Schiff base ligand and further bonded by two phenyl rings in a distorted cis-C₂SnNO₂ trigonal-bipyramidal geometry [C—Sn—C = 125.7 (2)°]. The two phenyl rings are oriented at a dihedral angle of 55.2 (3)°. Intramolecular O—H⋯N hydrogen bonding is present in the crystal structure.

Related literature

For the Sn(CH₃)₂(C₁₈H₁₁ClN₂O₃) analog, see: Lee et al. (2009 ).

Experimental

Crystal data

[Sn(C₆H₅)₂(C₁₈H₁₁ClN₂O₃)]
M_r = 611.63
Triclinic, $[P \overline 1]$
a = 10.5690 (4) Å
b = 10.9788 (4) Å
c = 11.8319 (4) Å
α = 68.381 (2)°
β = 82.450 (2)°
γ = 82.672 (2)°
V = 1260.60 (8) Å³
Z = 2
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 140 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.798, T_max = 1.000
6070 measured reflections
4280 independent reflections
3563 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.126
S = 1.05
4280 reflections
338 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.39 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—O1	2.057 (4)
Sn1—O2	2.150 (3)
Sn1—N1	2.166 (4)
Sn1—C1	2.131 (5)
Sn1—C7	2.124 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2	0.838 (10)	1.90 (4)	2.622 (6)	144 (6)

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/S1600536809050107/xu2687sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050107/xu2687Isup2.hkl

checkCIF report

Related literature top

For the Sn(CH₃)₂(C₁₈H₁₁ClN₂O₃) analog, see: Lee et al. (2009).

Experimental top

The Schiff base was prepared by the condensation of 3-hydroxy-2-naphthoylhydrazide and 5-chlorobenzaldehyde. The Schiff base (0.5 g, 1.5 mmol) and diphenyltin dichloride (0.52 g, 1.5 mmol) in a mixture (1:1) of methanol/chloroform was heated for 1 h. The filtered solution yielded the yellow crystals when allowed to evaporate slowly.

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 Sn(C₆H₅)₂(C₁₈H₁₁ClN₂O₃) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

[N'-(5-Chloro-2-oxidobenzylidene-κO)-3-hydroxy-2- naphthohydrazidato-κ²N',O²]diphenyltin(IV) top

Crystal data top

[Sn(C₆H₅)₂(C₁₈H₁₁ClN₂O₃)]	Z = 2
M_r = 611.63	F(000) = 612
Triclinic, P1	D_x = 1.611 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.5690 (4) Å	Cell parameters from 2361 reflections
b = 10.9788 (4) Å	θ = 2.5–26.8°
c = 11.8319 (4) Å	µ = 1.16 mm⁻¹
α = 68.381 (2)°	T = 140 K
β = 82.450 (2)°	Block, yellow
γ = 82.672 (2)°	0.30 × 0.25 × 0.20 mm
V = 1260.60 (8) Å³

Data collection top

Bruker SMART APEX diffractometer	4280 independent reflections
Radiation source: fine-focus sealed tube	3563 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→12
T_min = 0.798, T_max = 1.000	k = −12→13
6070 measured reflections	l = −14→14

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0736P)² + 1.6275P] where P = (F_o² + 2F_c²)/3
4280 reflections	(Δ/σ)_max = 0.001
338 parameters	Δρ_max = 1.39 e Å⁻³
1 restraint	Δρ_min = −0.70 e Å⁻³

Crystal data top

[Sn(C₆H₅)₂(C₁₈H₁₁ClN₂O₃)]	γ = 82.672 (2)°
M_r = 611.63	V = 1260.60 (8) Å³
Triclinic, P1	Z = 2
a = 10.5690 (4) Å	Mo Kα radiation
b = 10.9788 (4) Å	µ = 1.16 mm⁻¹
c = 11.8319 (4) Å	T = 140 K
α = 68.381 (2)°	0.30 × 0.25 × 0.20 mm
β = 82.450 (2)°

Data collection top

Bruker SMART APEX diffractometer	4280 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3563 reflections with I > 2σ(I)
T_min = 0.798, T_max = 1.000	R_int = 0.026
6070 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 1.39 e Å⁻³
4280 reflections	Δρ_min = −0.70 e Å⁻³
338 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.70294 (4)	0.27373 (3)	0.41404 (3)	0.02376 (15)
Cl1	0.26756 (16)	0.83455 (15)	0.05708 (14)	0.0421 (4)
O1	0.5939 (4)	0.3459 (4)	0.2678 (4)	0.0301 (9)
O2	0.8166 (3)	0.2790 (4)	0.5498 (3)	0.0260 (8)
O3	0.8095 (4)	0.6332 (4)	0.6156 (4)	0.0342 (9)
H3	0.785 (6)	0.626 (6)	0.554 (4)	0.036 (18)*
N1	0.6825 (4)	0.4749 (4)	0.4076 (4)	0.0227 (9)
N2	0.7518 (4)	0.5023 (4)	0.4861 (4)	0.0243 (10)
C1	0.8655 (5)	0.1998 (5)	0.3241 (5)	0.0239 (11)
C2	0.9726 (5)	0.1487 (5)	0.3839 (5)	0.0280 (12)
H2	0.9745	0.1478	0.4642	0.034*
C3	1.0794 (6)	0.0977 (6)	0.3278 (5)	0.0376 (15)
H3A	1.1540	0.0622	0.3698	0.045*
C4	1.0764 (6)	0.0992 (6)	0.2115 (6)	0.0399 (15)
H4	1.1484	0.0628	0.1738	0.048*
C5	0.9670 (6)	0.1543 (6)	0.1480 (5)	0.0346 (14)
H5	0.9659	0.1569	0.0670	0.041*
C6	0.8606 (6)	0.2049 (5)	0.2042 (5)	0.0306 (13)
H6	0.7861	0.2422	0.1624	0.037*
C7	0.5649 (5)	0.1587 (5)	0.5428 (5)	0.0256 (12)
C8	0.5989 (6)	0.0795 (5)	0.6585 (5)	0.0297 (13)
H8	0.6825	0.0785	0.6804	0.036*
C9	0.5098 (6)	0.0019 (6)	0.7421 (6)	0.0396 (15)
H9	0.5329	−0.0526	0.8211	0.047*
C10	0.3894 (6)	0.0032 (6)	0.7117 (6)	0.0403 (16)
H10	0.3294	−0.0505	0.7697	0.048*
C11	0.3539 (6)	0.0823 (6)	0.5971 (6)	0.0415 (16)
H11	0.2695	0.0847	0.5765	0.050*
C12	0.4438 (5)	0.1581 (6)	0.5126 (6)	0.0314 (13)
H12	0.4212	0.2102	0.4328	0.038*
C13	0.5173 (5)	0.4566 (5)	0.2272 (5)	0.0227 (11)
C14	0.4279 (5)	0.4645 (6)	0.1468 (5)	0.0297 (12)
H14	0.4196	0.3894	0.1275	0.036*
C15	0.3527 (6)	0.5769 (6)	0.0957 (5)	0.0336 (13)
H15	0.2928	0.5800	0.0413	0.040*
C16	0.3640 (6)	0.6880 (6)	0.1234 (5)	0.0311 (13)
C17	0.4479 (6)	0.6835 (6)	0.2032 (5)	0.0307 (13)
H17	0.4539	0.7593	0.2221	0.037*
C18	0.5258 (5)	0.5677 (5)	0.2580 (5)	0.0244 (11)
C19	0.6084 (5)	0.5730 (5)	0.3425 (5)	0.0266 (12)
H19	0.6091	0.6551	0.3520	0.032*
C20	0.8181 (5)	0.3960 (5)	0.5544 (5)	0.0247 (12)
C21	0.8990 (5)	0.4095 (5)	0.6409 (5)	0.0235 (11)
C22	0.8891 (5)	0.5257 (5)	0.6705 (5)	0.0248 (11)
C23	0.9596 (5)	0.5304 (5)	0.7572 (5)	0.0286 (12)
H23	0.9485	0.6059	0.7798	0.034*
C24	1.0496 (6)	0.4240 (5)	0.8146 (5)	0.0296 (13)
C25	1.1290 (6)	0.4294 (6)	0.8994 (5)	0.0338 (13)
H25	1.1199	0.5042	0.9229	0.041*
C26	1.2191 (6)	0.3278 (6)	0.9484 (5)	0.0384 (15)
H26	1.2726	0.3337	1.0044	0.046*
C27	1.2331 (6)	0.2150 (6)	0.9166 (5)	0.0353 (14)
H27	1.2963	0.1455	0.9501	0.042*
C28	1.1540 (5)	0.2065 (6)	0.8362 (5)	0.0307 (13)
H28	1.1618	0.1291	0.8166	0.037*
C29	1.0625 (5)	0.3094 (5)	0.7826 (5)	0.0244 (11)
C30	0.9820 (5)	0.3049 (5)	0.6981 (5)	0.0264 (12)
H30	0.9856	0.2268	0.6804	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0256 (2)	0.0222 (2)	0.0264 (2)	−0.00428 (14)	−0.00185 (14)	−0.01152 (15)
Cl1	0.0500 (10)	0.0377 (8)	0.0378 (8)	0.0106 (7)	−0.0166 (7)	−0.0129 (7)
O1	0.034 (2)	0.026 (2)	0.040 (2)	0.0033 (17)	−0.0167 (18)	−0.0194 (17)
O2	0.024 (2)	0.0249 (19)	0.033 (2)	0.0014 (15)	−0.0118 (16)	−0.0122 (16)
O3	0.046 (3)	0.027 (2)	0.035 (2)	0.0013 (19)	−0.0153 (19)	−0.0158 (18)
N1	0.022 (2)	0.025 (2)	0.023 (2)	−0.0039 (18)	−0.0017 (18)	−0.0104 (19)
N2	0.026 (2)	0.024 (2)	0.027 (2)	−0.0042 (19)	−0.0062 (19)	−0.0121 (19)
C1	0.015 (3)	0.020 (3)	0.037 (3)	−0.004 (2)	0.003 (2)	−0.011 (2)
C2	0.020 (3)	0.031 (3)	0.028 (3)	0.004 (2)	−0.004 (2)	−0.007 (2)
C3	0.026 (3)	0.042 (4)	0.036 (3)	0.011 (3)	−0.007 (3)	−0.006 (3)
C4	0.041 (4)	0.040 (3)	0.035 (3)	−0.002 (3)	0.010 (3)	−0.014 (3)
C5	0.039 (4)	0.037 (3)	0.027 (3)	−0.008 (3)	0.001 (3)	−0.011 (3)
C6	0.038 (3)	0.026 (3)	0.030 (3)	−0.014 (2)	0.003 (2)	−0.011 (2)
C7	0.022 (3)	0.028 (3)	0.032 (3)	−0.003 (2)	0.005 (2)	−0.019 (2)
C8	0.030 (3)	0.027 (3)	0.036 (3)	−0.002 (2)	0.001 (2)	−0.017 (2)
C9	0.049 (4)	0.030 (3)	0.040 (4)	−0.005 (3)	0.006 (3)	−0.016 (3)
C10	0.039 (4)	0.037 (3)	0.050 (4)	−0.017 (3)	0.017 (3)	−0.024 (3)
C11	0.033 (4)	0.045 (4)	0.062 (4)	−0.017 (3)	0.012 (3)	−0.038 (3)
C12	0.027 (3)	0.035 (3)	0.038 (3)	−0.002 (2)	0.000 (2)	−0.022 (3)
C13	0.014 (3)	0.027 (3)	0.025 (3)	0.002 (2)	−0.002 (2)	−0.009 (2)
C14	0.024 (3)	0.034 (3)	0.034 (3)	0.001 (2)	−0.010 (2)	−0.014 (3)
C15	0.030 (3)	0.035 (3)	0.033 (3)	0.002 (3)	−0.013 (2)	−0.007 (3)
C16	0.032 (3)	0.031 (3)	0.026 (3)	−0.003 (3)	0.003 (2)	−0.008 (2)
C17	0.035 (3)	0.033 (3)	0.027 (3)	−0.005 (3)	0.002 (2)	−0.015 (2)
C18	0.019 (3)	0.033 (3)	0.020 (3)	−0.006 (2)	0.000 (2)	−0.008 (2)
C19	0.028 (3)	0.027 (3)	0.028 (3)	−0.004 (2)	0.001 (2)	−0.014 (2)
C20	0.018 (3)	0.035 (3)	0.026 (3)	−0.011 (2)	0.005 (2)	−0.016 (2)
C21	0.017 (3)	0.029 (3)	0.027 (3)	−0.008 (2)	0.001 (2)	−0.012 (2)
C22	0.025 (3)	0.026 (3)	0.024 (3)	−0.008 (2)	0.001 (2)	−0.009 (2)
C23	0.036 (3)	0.025 (3)	0.027 (3)	−0.007 (2)	0.000 (2)	−0.011 (2)
C24	0.041 (3)	0.030 (3)	0.019 (3)	−0.016 (3)	0.003 (2)	−0.007 (2)
C25	0.044 (4)	0.033 (3)	0.026 (3)	−0.015 (3)	0.003 (3)	−0.010 (2)
C26	0.042 (4)	0.044 (4)	0.028 (3)	−0.012 (3)	−0.007 (3)	−0.007 (3)
C27	0.028 (3)	0.035 (3)	0.031 (3)	0.001 (3)	−0.006 (2)	0.001 (3)
C28	0.027 (3)	0.038 (3)	0.027 (3)	−0.006 (2)	−0.001 (2)	−0.011 (2)
C29	0.016 (3)	0.030 (3)	0.023 (3)	−0.001 (2)	−0.002 (2)	−0.005 (2)
C30	0.026 (3)	0.030 (3)	0.026 (3)	−0.003 (2)	−0.003 (2)	−0.013 (2)

Geometric parameters (Å, º) top

Sn1—O1	2.057 (4)	C11—C12	1.391 (8)
Sn1—O2	2.150 (3)	C11—H11	0.9500
Sn1—N1	2.166 (4)	C12—H12	0.9500
Sn1—C1	2.131 (5)	C13—C14	1.400 (7)
Sn1—C7	2.124 (5)	C13—C18	1.411 (8)
Cl1—C16	1.763 (6)	C14—C15	1.359 (8)
O1—C13	1.336 (6)	C14—H14	0.9500
O2—C20	1.308 (6)	C15—C16	1.397 (8)
O3—C22	1.360 (7)	C15—H15	0.9500
O3—H3	0.838 (10)	C16—C17	1.361 (8)
N1—C19	1.304 (7)	C17—C18	1.407 (8)
N1—N2	1.389 (6)	C17—H17	0.9500
N2—C20	1.323 (7)	C18—C19	1.433 (8)
C1—C2	1.361 (7)	C19—H19	0.9500
C1—C6	1.407 (8)	C20—C21	1.475 (7)
C2—C3	1.394 (8)	C21—C30	1.367 (8)
C2—H2	0.9500	C21—C22	1.431 (7)
C3—C4	1.375 (9)	C22—C23	1.364 (8)
C3—H3A	0.9500	C23—C24	1.426 (8)
C4—C5	1.408 (9)	C23—H23	0.9500
C4—H4	0.9500	C24—C25	1.411 (8)
C5—C6	1.389 (8)	C24—C29	1.427 (8)
C5—H5	0.9500	C25—C26	1.373 (9)
C6—H6	0.9500	C25—H25	0.9500
C7—C12	1.375 (8)	C26—C27	1.406 (9)
C7—C8	1.390 (8)	C26—H26	0.9500
C8—C9	1.389 (8)	C27—C28	1.381 (8)
C8—H8	0.9500	C27—H27	0.9500
C9—C10	1.364 (9)	C28—C29	1.404 (8)
C9—H9	0.9500	C28—H28	0.9500
C10—C11	1.385 (10)	C29—C30	1.413 (7)
C10—H10	0.9500	C30—H30	0.9500

O1—Sn1—C7	97.47 (19)	O1—C13—C18	123.0 (5)
O1—Sn1—C1	96.68 (18)	C14—C13—C18	118.5 (5)
C7—Sn1—C1	125.67 (19)	C15—C14—C13	121.6 (5)
O1—Sn1—O2	157.66 (14)	C15—C14—H14	119.2
C7—Sn1—O2	94.59 (18)	C13—C14—H14	119.2
C1—Sn1—O2	91.41 (18)	C14—C15—C16	119.7 (5)
O1—Sn1—N1	84.68 (15)	C14—C15—H15	120.2
C7—Sn1—N1	111.96 (17)	C16—C15—H15	120.2
C1—Sn1—N1	121.43 (17)	C17—C16—C15	120.5 (5)
O2—Sn1—N1	73.37 (15)	C17—C16—Cl1	119.4 (4)
C13—O1—Sn1	131.1 (3)	C15—C16—Cl1	120.1 (5)
C20—O2—Sn1	114.2 (3)	C16—C17—C18	120.7 (5)
C22—O3—H3	109 (4)	C16—C17—H17	119.6
C19—N1—N2	115.6 (4)	C18—C17—H17	119.6
C19—N1—Sn1	127.8 (4)	C17—C18—C13	118.9 (5)
N2—N1—Sn1	116.6 (3)	C17—C18—C19	116.0 (5)
C20—N2—N1	111.8 (4)	C13—C18—C19	125.1 (5)
C2—C1—C6	121.1 (5)	N1—C19—C18	125.7 (5)
C2—C1—Sn1	119.2 (4)	N1—C19—H19	117.2
C6—C1—Sn1	119.6 (4)	C18—C19—H19	117.2
C1—C2—C3	120.3 (5)	O2—C20—N2	123.9 (5)
C1—C2—H2	119.8	O2—C20—C21	117.6 (5)
C3—C2—H2	119.8	N2—C20—C21	118.4 (5)
C4—C3—C2	119.7 (6)	C30—C21—C22	119.4 (5)
C4—C3—H3A	120.1	C30—C21—C20	118.5 (5)
C2—C3—H3A	120.1	C22—C21—C20	122.0 (5)
C3—C4—C5	120.3 (6)	O3—C22—C23	118.0 (5)
C3—C4—H4	119.8	O3—C22—C21	122.0 (5)
C5—C4—H4	119.8	C23—C22—C21	120.0 (5)
C6—C5—C4	119.8 (6)	C22—C23—C24	121.2 (5)
C6—C5—H5	120.1	C22—C23—H23	119.4
C4—C5—H5	120.1	C24—C23—H23	119.4
C5—C6—C1	118.6 (6)	C25—C24—C23	122.3 (5)
C5—C6—H6	120.7	C25—C24—C29	118.8 (5)
C1—C6—H6	120.7	C23—C24—C29	118.8 (5)
C12—C7—C8	119.4 (5)	C26—C25—C24	120.8 (6)
C12—C7—Sn1	121.2 (4)	C26—C25—H25	119.6
C8—C7—Sn1	119.4 (4)	C24—C25—H25	119.6
C9—C8—C7	119.5 (6)	C25—C26—C27	120.7 (6)
C9—C8—H8	120.2	C25—C26—H26	119.6
C7—C8—H8	120.2	C27—C26—H26	119.6
C10—C9—C8	120.6 (6)	C28—C27—C26	119.3 (5)
C10—C9—H9	119.7	C28—C27—H27	120.3
C8—C9—H9	119.7	C26—C27—H27	120.3
C9—C10—C11	120.5 (6)	C27—C28—C29	121.5 (6)
C9—C10—H10	119.8	C27—C28—H28	119.3
C11—C10—H10	119.8	C29—C28—H28	119.3
C10—C11—C12	118.9 (6)	C28—C29—C30	122.9 (5)
C10—C11—H11	120.5	C28—C29—C24	118.8 (5)
C12—C11—H11	120.5	C30—C29—C24	118.3 (5)
C7—C12—C11	121.0 (6)	C21—C30—C29	122.1 (5)
C7—C12—H12	119.5	C21—C30—H30	119.0
C11—C12—H12	119.5	C29—C30—H30	119.0
O1—C13—C14	118.4 (5)

C7—Sn1—O1—C13	92.8 (5)	Sn1—O1—C13—C14	−162.6 (4)
C1—Sn1—O1—C13	−139.8 (5)	Sn1—O1—C13—C18	20.0 (8)
O2—Sn1—O1—C13	−29.3 (7)	O1—C13—C14—C15	−175.7 (5)
N1—Sn1—O1—C13	−18.7 (5)	C18—C13—C14—C15	1.9 (8)
O1—Sn1—O2—C20	8.6 (6)	C13—C14—C15—C16	0.0 (9)
C7—Sn1—O2—C20	−113.9 (4)	C14—C15—C16—C17	−1.4 (9)
C1—Sn1—O2—C20	120.1 (4)	C14—C15—C16—Cl1	179.7 (5)
N1—Sn1—O2—C20	−2.3 (3)	C15—C16—C17—C18	0.8 (8)
O1—Sn1—N1—C19	9.4 (4)	Cl1—C16—C17—C18	179.8 (4)
C7—Sn1—N1—C19	−86.5 (5)	C16—C17—C18—C13	1.1 (8)
C1—Sn1—N1—C19	104.0 (5)	C16—C17—C18—C19	−178.6 (5)
O2—Sn1—N1—C19	−174.8 (5)	O1—C13—C18—C17	175.0 (5)
O1—Sn1—N1—N2	−173.9 (3)	C14—C13—C18—C17	−2.4 (8)
C7—Sn1—N1—N2	90.2 (4)	O1—C13—C18—C19	−5.2 (8)
C1—Sn1—N1—N2	−79.3 (4)	C14—C13—C18—C19	177.3 (5)
O2—Sn1—N1—N2	1.9 (3)	N2—N1—C19—C18	−178.3 (5)
C19—N1—N2—C20	175.9 (5)	Sn1—N1—C19—C18	−1.6 (8)
Sn1—N1—N2—C20	−1.2 (5)	C17—C18—C19—N1	176.1 (5)
O1—Sn1—C1—C2	175.0 (4)	C13—C18—C19—N1	−3.7 (9)
C7—Sn1—C1—C2	−80.8 (5)	Sn1—O2—C20—N2	2.8 (6)
O2—Sn1—C1—C2	15.9 (4)	Sn1—O2—C20—C21	−177.0 (3)
N1—Sn1—C1—C2	87.2 (5)	N1—N2—C20—O2	−1.1 (7)
O1—Sn1—C1—C6	−4.8 (4)	N1—N2—C20—C21	178.7 (4)
C7—Sn1—C1—C6	99.4 (4)	O2—C20—C21—C30	9.5 (7)
O2—Sn1—C1—C6	−163.9 (4)	N2—C20—C21—C30	−170.4 (5)
N1—Sn1—C1—C6	−92.6 (4)	O2—C20—C21—C22	−167.7 (5)
C6—C1—C2—C3	−1.3 (8)	N2—C20—C21—C22	12.5 (7)
Sn1—C1—C2—C3	178.9 (4)	C30—C21—C22—O3	179.2 (5)
C1—C2—C3—C4	0.0 (9)	C20—C21—C22—O3	−3.7 (8)
C2—C3—C4—C5	1.3 (9)	C30—C21—C22—C23	−1.6 (8)
C3—C4—C5—C6	−1.4 (9)	C20—C21—C22—C23	175.5 (5)
C4—C5—C6—C1	0.2 (8)	O3—C22—C23—C24	−177.0 (5)
C2—C1—C6—C5	1.2 (8)	C21—C22—C23—C24	3.8 (8)
Sn1—C1—C6—C5	−179.0 (4)	C22—C23—C24—C25	176.3 (5)
O1—Sn1—C7—C12	−3.0 (4)	C22—C23—C24—C29	−1.9 (8)
C1—Sn1—C7—C12	−106.8 (4)	C23—C24—C25—C26	−176.8 (5)
O2—Sn1—C7—C12	158.1 (4)	C29—C24—C25—C26	1.5 (8)
N1—Sn1—C7—C12	84.2 (4)	C24—C25—C26—C27	−1.0 (9)
O1—Sn1—C7—C8	175.0 (4)	C25—C26—C27—C28	−0.7 (9)
C1—Sn1—C7—C8	71.2 (5)	C26—C27—C28—C29	1.9 (9)
O2—Sn1—C7—C8	−23.8 (4)	C27—C28—C29—C30	178.6 (5)
N1—Sn1—C7—C8	−97.7 (4)	C27—C28—C29—C24	−1.4 (8)
C12—C7—C8—C9	−0.5 (8)	C25—C24—C29—C28	−0.3 (8)
Sn1—C7—C8—C9	−178.6 (4)	C23—C24—C29—C28	178.0 (5)
C7—C8—C9—C10	−0.3 (8)	C25—C24—C29—C30	179.7 (5)
C8—C9—C10—C11	−0.2 (9)	C23—C24—C29—C30	−2.0 (7)
C9—C10—C11—C12	1.4 (9)	C22—C21—C30—C29	−2.5 (8)
C8—C7—C12—C11	1.8 (8)	C20—C21—C30—C29	−179.7 (5)
Sn1—C7—C12—C11	179.8 (4)	C28—C29—C30—C21	−175.7 (5)
C10—C11—C12—C7	−2.2 (8)	C24—C29—C30—C21	4.3 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.84 (1)	1.90 (4)	2.622 (6)	144 (6)

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₂(C₁₈H₁₁ClN₂O₃)]
M_r	611.63
Crystal system, space group	Triclinic, P1
Temperature (K)	140
a, b, c (Å)	10.5690 (4), 10.9788 (4), 11.8319 (4)
α, β, γ (°)	68.381 (2), 82.450 (2), 82.672 (2)
V (Å³)	1260.60 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.16
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.798, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6070, 4280, 3563
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.126, 1.05
No. of reflections	4280
No. of parameters	338
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.39, −0.70

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

Selected bond lengths (Å) top

Sn1—O1	2.057 (4)	Sn1—C1	2.131 (5)
Sn1—O2	2.150 (3)	Sn1—C7	2.124 (5)
Sn1—N1	2.166 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.838 (10)	1.90 (4)	2.622 (6)	144 (6)

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lee, S. M., Lo, K. M., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, m816. Web of Science CSD CrossRef IUCr Journals 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
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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