[4-Chloro-N′-(3-meth­oxy-2-oxidobenzyl­idene)benzohydrazidato]diphenyl­tin(IV)

Cui, J.; Yin, H.; Qiao, Y.

doi:10.1107/S1600536807062307

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[4-Chloro-N'-(3-methoxy-2-oxidobenzylidene)benzohydrazidato]diphenyltin(IV)

J. Cui, H. Yin and Y. Qiao

The title compound, [Sn(C₆H₅)₂(C₁₅H₁₁ClN₂O₃)], crystallizes with two independent molecules in the asymmetric unit with almost identical conformation. In each molecule, the Sn atom is coordinated by two O, one N and two C atoms in a distorted trigonal-bipyramidal geometry [Sn-O = 2.066 (3)-2.132 (4) Å, and Sn-N = 2.150 (4) and 2.141 (4) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807062307/dn2284sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807062307/dn2284Isup2.hkl Contains datablock I

CCDC reference: 672773

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.009 Å
R factor = 0.045
wR factor = 0.087
Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.61 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C24
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C32
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C49
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C16    -C21           1.37 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C22    -C27           1.37 Ang.
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Recently, we have reported some organotin(IV) complexes with Schiff base of o-vanillin-2-thiophenoylhydrazone (Yin, Chen, 2006). As an extension of our work on the organotin(IV) Schiff bases chemistry, the title compound, (I), is reported here (Fig. 1).

In the title compound, (I), the Sn atom has a distorted trigonal-bipyramidal geometry, with atoms O1 (O4) and O2 (O5) in axial positions [O1—Sn1—O2 = 158.33 (13)°, O4—Sn2—O5 = 156.14 (15)°] and the atoms C16 (C43), C22 (C49)] and N1 (N3) in equatorial positions. The sum of the equatorial angles is 359.43 ° (359.86 °), indicating approximate coplanarity for these atoms. The Sn1—N1 (Sn2—N3) bond length is 2.150 (4) Å (2.141 (4) Å) close to the sum of the non-polar covalent radii 2.15 Å, indicate a strong Sn—N interaction. The O atoms coordinate to the Sn atom with one shorter and one longer Sn—O bond.

Related literature top

For a related structure, see: Yin & Chen (2006).

Experimental top

The reaction was carried out under nitrogen atmosphere. o-vanillin 4-chlorobenzhydrazone(1 mmol) and sodium ethoxide (1.2 mmol) were added to the solution of benzene(30 ml) in a Schlenk flask and stirred for 0.5 h. Diphenyltin dichloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 4 h at 313 K·The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (1:1)·Analysis calculated for C₂₇H₂₁ClN₂O₃Sn (Mr = 575.63): C, 56.34; H, 3.68; N, 4.87, found: C, 56.28; H, 3.61; N, 4.95.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity.

[4-Chloro-N'-(3-methoxy-2-oxidobenzylidene)benzohydrazidato]diphenyltin(IV) top

Crystal data top

[Sn(C₆H₅)₂(C₁₅H₁₁ClN₂O₃)]	F(000) = 2304
M_r = 575.60	D_x = 1.554 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4610 reflections
a = 19.178 (2) Å	θ = 2.3–27.3°
b = 27.968 (3) Å	µ = 1.18 mm⁻¹
c = 9.4230 (13) Å	T = 298 K
β = 103.238 (2)°	Block, orange
V = 4920.1 (10) Å³	0.37 × 0.17 × 0.12 mm
Z = 8

Data collection top

CCD area-detector diffractometer	8658 independent reflections
Radiation source: fine-focus sealed tube	5197 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
T_min = 0.670, T_max = 0.872	k = −25→33
20342 measured reflections	l = −10→11

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0253P)² + 2.1263P] where P = (F_o² + 2F_c²)/3
8658 reflections	(Δ/σ)_max = 0.002
615 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.76 e Å⁻³

Crystal data top

[Sn(C₆H₅)₂(C₁₅H₁₁ClN₂O₃)]	V = 4920.1 (10) Å³
M_r = 575.60	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.178 (2) Å	µ = 1.18 mm⁻¹
b = 27.968 (3) Å	T = 298 K
c = 9.4230 (13) Å	0.37 × 0.17 × 0.12 mm
β = 103.238 (2)°

Data collection top

CCD area-detector diffractometer	8658 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5197 reflections with I > 2σ(I)
T_min = 0.670, T_max = 0.872	R_int = 0.045
20342 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.01	Δρ_max = 0.54 e Å⁻³
8658 reflections	Δρ_min = −0.76 e Å⁻³
615 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Sn1	0.144802 (18)	0.519068 (13)	0.41711 (4)	0.04606 (12)
Sn2	0.501802 (19)	0.854204 (13)	0.48215 (4)	0.05022 (13)
Cl1	0.12874 (10)	0.25504 (6)	0.9118 (2)	0.1020 (6)
Cl2	0.14114 (9)	0.77336 (6)	0.8586 (2)	0.0956 (6)
N1	0.0499 (2)	0.47593 (15)	0.3566 (5)	0.0479 (11)
N2	0.0496 (2)	0.43350 (15)	0.4343 (5)	0.0559 (12)
N3	0.4951 (2)	0.78151 (15)	0.5491 (5)	0.0497 (12)
N4	0.4407 (2)	0.77048 (15)	0.6197 (5)	0.0547 (12)
O1	0.15977 (18)	0.45977 (12)	0.5633 (4)	0.0584 (10)
O2	0.09344 (17)	0.56387 (12)	0.2515 (4)	0.0527 (10)
O3	0.05732 (19)	0.63653 (14)	0.0770 (4)	0.0699 (12)
O4	0.40729 (17)	0.84888 (13)	0.5635 (4)	0.0620 (11)
O5	0.59883 (17)	0.83215 (13)	0.4450 (4)	0.0575 (10)
O6	0.7019 (2)	0.82949 (16)	0.3078 (5)	0.0771 (12)
C1	0.1073 (3)	0.4291 (2)	0.5375 (6)	0.0484 (14)
C2	0.1135 (3)	0.3856 (2)	0.6272 (6)	0.0508 (14)
C3	0.0614 (3)	0.3497 (2)	0.5990 (7)	0.0724 (18)
H3	0.0224	0.3526	0.5201	0.087*
C4	0.0673 (4)	0.3101 (2)	0.6865 (8)	0.0750 (19)
H4	0.0325	0.2864	0.6663	0.090*
C5	0.1236 (4)	0.3053 (2)	0.8025 (8)	0.0665 (18)
C6	0.1762 (3)	0.3391 (2)	0.8317 (7)	0.0737 (19)
H6	0.2155	0.3351	0.9095	0.088*
C7	0.1706 (3)	0.3793 (2)	0.7444 (7)	0.0630 (16)
H7	0.2061	0.4026	0.7654	0.076*
C8	−0.0062 (3)	0.48431 (19)	0.2528 (6)	0.0520 (14)
H8	−0.0416	0.4609	0.2375	0.062*
C9	−0.0202 (3)	0.52482 (19)	0.1600 (5)	0.0439 (13)
C10	0.0286 (3)	0.56267 (19)	0.1631 (6)	0.0472 (14)
C11	0.0074 (3)	0.6005 (2)	0.0660 (6)	0.0484 (14)
C12	−0.0584 (3)	0.6004 (2)	−0.0299 (6)	0.0636 (17)
H12	−0.0715	0.6258	−0.0941	0.076*
C13	−0.1056 (3)	0.5626 (2)	−0.0319 (7)	0.0667 (17)
H13	−0.1501	0.5628	−0.0969	0.080*
C14	−0.0870 (3)	0.5258 (2)	0.0593 (6)	0.0562 (15)
H14	−0.1187	0.5004	0.0563	0.067*
C15	0.0361 (3)	0.6782 (2)	−0.0083 (7)	0.089 (2)
H15A	0.0290	0.6703	−0.1098	0.133*
H15B	0.0728	0.7021	0.0168	0.133*
H15C	−0.0078	0.6903	0.0105	0.133*
C16	0.1542 (2)	0.57022 (19)	0.5832 (6)	0.0425 (13)
C17	0.1312 (3)	0.6159 (2)	0.5540 (6)	0.0654 (17)
H17	0.1108	0.6247	0.4584	0.078*
C18	0.1376 (4)	0.6494 (2)	0.6643 (8)	0.084 (2)
H18	0.1214	0.6805	0.6423	0.101*
C19	0.1677 (4)	0.6372 (2)	0.8048 (7)	0.0751 (19)
H19	0.1721	0.6597	0.8789	0.090*
C20	0.1911 (3)	0.5918 (3)	0.8352 (7)	0.080 (2)
H20	0.2110	0.5830	0.9312	0.096*
C21	0.1858 (3)	0.5588 (2)	0.7265 (7)	0.0636 (17)
H21	0.2037	0.5282	0.7491	0.076*
C22	0.2308 (3)	0.5003 (2)	0.3235 (6)	0.0464 (13)
C23	0.2741 (3)	0.4618 (2)	0.3749 (7)	0.0796 (19)
H23	0.2664	0.4440	0.4534	0.096*
C24	0.3291 (4)	0.4496 (3)	0.3086 (10)	0.112 (3)
H24	0.3578	0.4233	0.3425	0.134*
C25	0.3419 (4)	0.4752 (3)	0.1961 (9)	0.100 (3)
H25	0.3793	0.4666	0.1533	0.120*
C26	0.3006 (4)	0.5131 (3)	0.1460 (8)	0.090 (2)
H26	0.3095	0.5309	0.0688	0.108*
C27	0.2453 (3)	0.5254 (2)	0.2085 (7)	0.0681 (17)
H27	0.2167	0.5516	0.1720	0.082*
C28	0.3999 (3)	0.8073 (2)	0.6217 (6)	0.0497 (14)
C29	0.3380 (3)	0.80035 (18)	0.6884 (6)	0.0450 (13)
C30	0.2846 (3)	0.83445 (19)	0.6718 (6)	0.0517 (15)
H30	0.2893	0.8629	0.6237	0.062*
C31	0.2243 (3)	0.82690 (19)	0.7259 (6)	0.0546 (15)
H31	0.1885	0.8500	0.7147	0.065*
C32	0.2182 (3)	0.7847 (2)	0.7965 (6)	0.0587 (16)
C33	0.2704 (3)	0.7508 (2)	0.8147 (7)	0.0763 (19)
H33	0.2657	0.7225	0.8632	0.092*
C34	0.3297 (3)	0.7589 (2)	0.7611 (7)	0.0689 (18)
H34	0.3653	0.7357	0.7740	0.083*
C35	0.5305 (3)	0.7454 (2)	0.5154 (6)	0.0590 (16)
H35	0.5175	0.7154	0.5433	0.071*
C36	0.5869 (3)	0.7465 (2)	0.4408 (6)	0.0554 (15)
C37	0.6176 (3)	0.7894 (2)	0.4070 (6)	0.0512 (15)
C38	0.6743 (3)	0.7866 (2)	0.3343 (6)	0.0590 (16)
C39	0.6974 (3)	0.7431 (3)	0.2950 (7)	0.0726 (19)
H39	0.7342	0.7419	0.2459	0.087*
C40	0.6663 (4)	0.7012 (3)	0.3279 (7)	0.082 (2)
H40	0.6826	0.6720	0.3012	0.099*
C41	0.6117 (3)	0.7024 (2)	0.3992 (7)	0.0727 (19)
H41	0.5909	0.6740	0.4203	0.087*
C42	0.7613 (3)	0.8289 (2)	0.2383 (8)	0.099 (2)
H42A	0.7992	0.8097	0.2945	0.149*
H42B	0.7783	0.8610	0.2319	0.149*
H42C	0.7461	0.8157	0.1421	0.149*
C43	0.4510 (3)	0.86868 (17)	0.2621 (6)	0.0517 (15)
C44	0.4930 (3)	0.87867 (19)	0.1658 (7)	0.0666 (17)
H44	0.5425	0.8767	0.1969	0.080*
C45	0.4628 (4)	0.8915 (2)	0.0243 (8)	0.084 (2)
H45	0.4920	0.8991	−0.0389	0.101*
C46	0.3906 (5)	0.8930 (3)	−0.0232 (8)	0.101 (3)
H46	0.3704	0.9014	−0.1193	0.121*
C47	0.3473 (4)	0.8823 (2)	0.0689 (10)	0.091 (2)
H47	0.2977	0.8828	0.0354	0.109*
C48	0.3776 (3)	0.8707 (2)	0.2124 (8)	0.0718 (18)
H48	0.3482	0.8641	0.2760	0.086*
C49	0.5474 (3)	0.91054 (18)	0.6191 (6)	0.0481 (14)
C50	0.5057 (3)	0.9406 (2)	0.6795 (7)	0.080 (2)
H50	0.4570	0.9343	0.6659	0.096*
C51	0.5347 (5)	0.9802 (3)	0.7605 (8)	0.105 (3)
H51	0.5057	0.9999	0.8016	0.126*
C52	0.6051 (5)	0.9899 (3)	0.7797 (9)	0.108 (3)
H52	0.6243	1.0167	0.8327	0.130*
C53	0.6480 (4)	0.9606 (3)	0.7221 (8)	0.097 (2)
H53	0.6966	0.9674	0.7363	0.117*
C54	0.6196 (3)	0.9211 (2)	0.6425 (7)	0.0704 (18)
H54	0.6493	0.9011	0.6039	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0419 (2)	0.0469 (2)	0.0478 (2)	−0.00302 (17)	0.00702 (17)	0.0001 (2)
Sn2	0.0486 (2)	0.0417 (2)	0.0617 (3)	−0.00054 (18)	0.01537 (19)	0.0007 (2)
Cl1	0.1256 (16)	0.0735 (13)	0.1236 (16)	0.0273 (10)	0.0628 (13)	0.0444 (12)
Cl2	0.0946 (13)	0.0798 (13)	0.1330 (17)	−0.0108 (10)	0.0691 (12)	0.0045 (11)
N1	0.044 (3)	0.047 (3)	0.051 (3)	−0.004 (2)	0.009 (2)	0.002 (2)
N2	0.056 (3)	0.048 (3)	0.063 (3)	−0.008 (2)	0.012 (3)	0.010 (3)
N3	0.048 (3)	0.037 (3)	0.064 (3)	0.003 (2)	0.013 (2)	0.007 (2)
N4	0.049 (3)	0.038 (3)	0.079 (4)	0.002 (2)	0.019 (3)	0.009 (2)
O1	0.051 (2)	0.053 (2)	0.064 (3)	−0.0073 (19)	−0.0029 (19)	0.013 (2)
O2	0.043 (2)	0.057 (2)	0.053 (2)	−0.0029 (17)	0.0003 (19)	0.0101 (19)
O3	0.063 (3)	0.064 (3)	0.079 (3)	−0.001 (2)	0.008 (2)	0.021 (2)
O4	0.060 (2)	0.040 (2)	0.095 (3)	0.0040 (18)	0.037 (2)	0.014 (2)
O5	0.051 (2)	0.046 (2)	0.080 (3)	0.0015 (17)	0.022 (2)	−0.008 (2)
O6	0.063 (3)	0.083 (3)	0.093 (3)	−0.001 (2)	0.032 (2)	−0.012 (3)
C1	0.044 (3)	0.058 (4)	0.046 (4)	−0.001 (3)	0.016 (3)	0.004 (3)
C2	0.055 (4)	0.048 (4)	0.054 (4)	0.001 (3)	0.022 (3)	−0.001 (3)
C3	0.068 (4)	0.063 (5)	0.083 (5)	0.001 (4)	0.011 (4)	0.011 (4)
C4	0.091 (5)	0.045 (4)	0.098 (6)	−0.005 (4)	0.040 (5)	0.014 (4)
C5	0.074 (5)	0.055 (4)	0.079 (5)	0.019 (4)	0.033 (4)	0.014 (4)
C6	0.072 (5)	0.075 (5)	0.076 (5)	0.020 (4)	0.020 (4)	0.015 (4)
C7	0.067 (4)	0.055 (4)	0.066 (4)	0.001 (3)	0.013 (4)	0.008 (4)
C8	0.043 (3)	0.051 (4)	0.062 (4)	0.001 (3)	0.012 (3)	−0.008 (3)
C9	0.044 (3)	0.047 (4)	0.039 (3)	0.009 (3)	0.006 (3)	−0.007 (3)
C10	0.047 (3)	0.055 (4)	0.041 (3)	0.008 (3)	0.012 (3)	−0.002 (3)
C11	0.051 (4)	0.048 (4)	0.046 (4)	0.002 (3)	0.010 (3)	0.000 (3)
C12	0.070 (4)	0.066 (5)	0.052 (4)	0.020 (4)	0.007 (3)	0.004 (3)
C13	0.053 (4)	0.070 (5)	0.069 (5)	0.000 (4)	−0.003 (3)	−0.011 (4)
C14	0.047 (4)	0.062 (4)	0.053 (4)	0.003 (3)	−0.001 (3)	−0.006 (3)
C15	0.076 (5)	0.078 (5)	0.113 (6)	0.008 (4)	0.024 (4)	0.037 (5)
C16	0.039 (3)	0.044 (4)	0.047 (4)	−0.004 (2)	0.015 (3)	0.000 (3)
C17	0.085 (5)	0.061 (5)	0.043 (4)	0.009 (3)	0.000 (3)	−0.005 (3)
C18	0.123 (6)	0.058 (5)	0.066 (5)	0.024 (4)	0.012 (4)	−0.002 (4)
C19	0.102 (5)	0.064 (5)	0.060 (5)	−0.013 (4)	0.018 (4)	−0.018 (4)
C20	0.113 (6)	0.080 (6)	0.044 (4)	−0.005 (4)	0.010 (4)	0.005 (4)
C21	0.077 (4)	0.053 (4)	0.056 (4)	0.013 (3)	0.004 (3)	−0.002 (3)
C22	0.041 (3)	0.055 (4)	0.042 (3)	0.004 (3)	0.006 (3)	−0.007 (3)
C23	0.075 (5)	0.085 (5)	0.082 (5)	0.020 (4)	0.024 (4)	0.007 (4)
C24	0.103 (6)	0.111 (7)	0.135 (8)	0.053 (5)	0.056 (6)	0.013 (6)
C25	0.067 (5)	0.134 (8)	0.105 (7)	0.022 (5)	0.034 (5)	−0.025 (6)
C26	0.075 (5)	0.124 (7)	0.082 (5)	0.004 (5)	0.041 (4)	0.010 (5)
C27	0.056 (4)	0.077 (5)	0.073 (5)	0.009 (3)	0.021 (3)	0.005 (4)
C28	0.050 (3)	0.042 (4)	0.055 (4)	−0.007 (3)	0.010 (3)	0.000 (3)
C29	0.044 (3)	0.039 (4)	0.050 (4)	−0.006 (3)	0.006 (3)	0.005 (3)
C30	0.057 (4)	0.044 (4)	0.054 (4)	0.002 (3)	0.013 (3)	0.014 (3)
C31	0.057 (4)	0.040 (4)	0.068 (4)	0.009 (3)	0.019 (3)	−0.003 (3)
C32	0.056 (4)	0.055 (4)	0.066 (4)	−0.006 (3)	0.015 (3)	0.000 (3)
C33	0.084 (5)	0.060 (4)	0.094 (5)	−0.001 (4)	0.039 (4)	0.034 (4)
C34	0.055 (4)	0.060 (4)	0.090 (5)	0.008 (3)	0.014 (3)	0.033 (4)
C35	0.058 (4)	0.044 (4)	0.071 (4)	0.006 (3)	0.006 (3)	0.003 (3)
C36	0.049 (4)	0.056 (4)	0.056 (4)	0.009 (3)	0.002 (3)	−0.008 (3)
C37	0.040 (3)	0.056 (4)	0.050 (4)	0.010 (3)	−0.004 (3)	−0.007 (3)
C38	0.051 (4)	0.055 (5)	0.069 (4)	−0.001 (3)	0.009 (3)	−0.014 (3)
C39	0.063 (4)	0.078 (5)	0.075 (5)	0.010 (4)	0.013 (3)	−0.018 (4)
C40	0.087 (5)	0.065 (5)	0.096 (6)	0.019 (4)	0.022 (4)	−0.024 (4)
C41	0.073 (4)	0.052 (4)	0.089 (5)	0.013 (3)	0.008 (4)	−0.004 (4)
C42	0.084 (5)	0.108 (6)	0.121 (7)	−0.001 (4)	0.057 (5)	−0.006 (5)
C43	0.055 (4)	0.033 (3)	0.065 (4)	−0.004 (3)	0.010 (3)	−0.008 (3)
C44	0.070 (4)	0.059 (4)	0.070 (5)	−0.006 (3)	0.014 (4)	0.002 (4)
C45	0.112 (6)	0.088 (6)	0.053 (5)	0.008 (5)	0.019 (4)	0.009 (4)
C46	0.129 (8)	0.094 (6)	0.065 (6)	0.010 (6)	−0.009 (6)	−0.008 (5)
C47	0.070 (5)	0.092 (6)	0.092 (6)	−0.001 (4)	−0.023 (5)	−0.013 (5)
C48	0.058 (4)	0.066 (5)	0.086 (5)	−0.006 (3)	0.005 (4)	−0.008 (4)
C49	0.052 (4)	0.037 (3)	0.055 (4)	0.005 (3)	0.012 (3)	0.005 (3)
C50	0.071 (4)	0.075 (5)	0.090 (5)	0.004 (4)	0.010 (4)	−0.027 (4)
C51	0.117 (7)	0.083 (6)	0.109 (7)	0.029 (5)	0.012 (5)	−0.036 (5)
C52	0.122 (7)	0.063 (6)	0.119 (7)	−0.002 (5)	−0.014 (6)	−0.032 (5)
C53	0.078 (5)	0.072 (6)	0.130 (7)	−0.014 (4)	−0.003 (5)	−0.022 (5)
C54	0.061 (4)	0.057 (4)	0.090 (5)	−0.003 (3)	0.013 (4)	−0.010 (4)

Geometric parameters (Å, º) top

Sn1—O2	2.067 (3)	C20—H20	0.9300
Sn1—C16	2.097 (5)	C21—H21	0.9300
Sn1—C22	2.107 (5)	C22—C27	1.372 (7)
Sn1—O1	2.133 (3)	C22—C23	1.379 (7)
Sn1—N1	2.149 (4)	C23—C24	1.387 (8)
Sn2—O5	2.065 (3)	C23—H23	0.9300
Sn2—C49	2.097 (5)	C24—C25	1.347 (9)
Sn2—C43	2.119 (6)	C24—H24	0.9300
Sn2—O4	2.129 (3)	C25—C26	1.343 (9)
Sn2—N3	2.141 (4)	C25—H25	0.9300
Cl1—C5	1.733 (6)	C26—C27	1.370 (8)
Cl2—C32	1.739 (6)	C26—H26	0.9300
N1—C8	1.299 (6)	C27—H27	0.9300
N1—N2	1.395 (5)	C28—C29	1.477 (7)
N2—C1	1.301 (6)	C29—C34	1.375 (7)
N3—C35	1.296 (6)	C29—C30	1.382 (6)
N3—N4	1.395 (5)	C30—C31	1.383 (7)
N4—C28	1.297 (6)	C30—H30	0.9300
O1—C1	1.303 (6)	C31—C32	1.372 (7)
O2—C10	1.330 (5)	C31—H31	0.9300
O3—C11	1.377 (6)	C32—C33	1.361 (7)
O3—C15	1.421 (6)	C33—C34	1.364 (7)
O4—C28	1.307 (6)	C33—H33	0.9300
O5—C37	1.321 (6)	C34—H34	0.9300
O6—C38	1.358 (6)	C35—C36	1.418 (7)
O6—C42	1.439 (6)	C35—H35	0.9300
C1—C2	1.469 (7)	C36—C37	1.406 (7)
C2—C7	1.377 (7)	C36—C41	1.410 (7)
C2—C3	1.400 (7)	C37—C38	1.413 (7)
C3—C4	1.368 (7)	C38—C39	1.373 (7)
C3—H3	0.9300	C39—C40	1.382 (8)
C4—C5	1.355 (8)	C39—H39	0.9300
C4—H4	0.9300	C40—C41	1.367 (8)
C5—C6	1.363 (8)	C40—H40	0.9300
C6—C7	1.383 (7)	C41—H41	0.9300
C6—H6	0.9300	C42—H42A	0.9600
C7—H7	0.9300	C42—H42B	0.9600
C8—C9	1.419 (7)	C42—H42C	0.9600
C8—H8	0.9300	C43—C44	1.373 (7)
C9—C10	1.408 (7)	C43—C48	1.379 (7)
C9—C14	1.409 (6)	C44—C45	1.374 (8)
C10—C11	1.398 (7)	C44—H44	0.9300
C11—C12	1.374 (7)	C45—C46	1.355 (9)
C12—C13	1.389 (7)	C45—H45	0.9300
C12—H12	0.9300	C46—C47	1.365 (9)
C13—C14	1.335 (7)	C46—H46	0.9300
C13—H13	0.9300	C47—C48	1.383 (9)
C14—H14	0.9300	C47—H47	0.9300
C15—H15A	0.9600	C48—H48	0.9300
C15—H15B	0.9600	C49—C50	1.371 (7)
C15—H15C	0.9600	C49—C54	1.382 (7)
C16—C17	1.358 (7)	C50—C51	1.386 (8)
C16—C21	1.385 (7)	C50—H50	0.9300
C17—C18	1.385 (7)	C51—C52	1.347 (9)
C17—H17	0.9300	C51—H51	0.9300
C18—C19	1.361 (8)	C52—C53	1.360 (9)
C18—H18	0.9300	C52—H52	0.9300
C19—C20	1.355 (8)	C53—C54	1.377 (8)
C19—H19	0.9300	C53—H53	0.9300
C20—C21	1.364 (8)	C54—H54	0.9300

O2—Sn1—C16	95.42 (18)	C27—C22—Sn1	121.5 (4)
O2—Sn1—C22	96.78 (18)	C23—C22—Sn1	120.9 (4)
C16—Sn1—C22	122.71 (18)	C22—C23—C24	119.5 (7)
O2—Sn1—O1	158.35 (13)	C22—C23—H23	120.2
C16—Sn1—O1	94.18 (18)	C24—C23—H23	120.2
C22—Sn1—O1	94.26 (18)	C25—C24—C23	121.2 (7)
O2—Sn1—N1	84.94 (15)	C25—C24—H24	119.4
C16—Sn1—N1	120.24 (16)	C23—C24—H24	119.4
C22—Sn1—N1	116.48 (17)	C26—C25—C24	119.8 (7)
O1—Sn1—N1	73.46 (15)	C26—C25—H25	120.1
O5—Sn2—C49	93.66 (17)	C24—C25—H25	120.1
O5—Sn2—C43	96.99 (19)	C25—C26—C27	120.1 (7)
C49—Sn2—C43	119.50 (19)	C25—C26—H26	120.0
O5—Sn2—O4	156.18 (14)	C27—C26—H26	120.0
C49—Sn2—O4	95.77 (18)	C26—C27—C22	121.8 (6)
C43—Sn2—O4	97.29 (19)	C26—C27—H27	119.1
O5—Sn2—N3	83.29 (15)	C22—C27—H27	119.1
C49—Sn2—N3	125.24 (18)	N4—C28—O4	125.2 (5)
C43—Sn2—N3	115.12 (17)	N4—C28—C29	116.6 (5)
O4—Sn2—N3	73.40 (15)	O4—C28—C29	118.1 (5)
C8—N1—N2	116.5 (4)	C34—C29—C30	118.1 (5)
C8—N1—Sn1	127.1 (4)	C34—C29—C28	121.3 (5)
N2—N1—Sn1	116.3 (3)	C30—C29—C28	120.5 (5)
C1—N2—N1	111.6 (4)	C29—C30—C31	120.9 (5)
C35—N3—N4	115.8 (4)	C29—C30—H30	119.5
C35—N3—Sn2	126.7 (4)	C31—C30—H30	119.5
N4—N3—Sn2	116.9 (3)	C32—C31—C30	118.7 (5)
C28—N4—N3	110.6 (4)	C32—C31—H31	120.6
C1—O1—Sn1	114.1 (3)	C30—C31—H31	120.6
C10—O2—Sn1	132.3 (3)	C33—C32—C31	121.3 (5)
C11—O3—C15	116.9 (4)	C33—C32—Cl2	119.1 (5)
C28—O4—Sn2	113.4 (3)	C31—C32—Cl2	119.6 (5)
C37—O5—Sn2	129.0 (3)	C32—C33—C34	119.2 (6)
C38—O6—C42	117.2 (5)	C32—C33—H33	120.4
N2—C1—O1	124.4 (5)	C34—C33—H33	120.4
N2—C1—C2	116.9 (5)	C33—C34—C29	121.7 (5)
O1—C1—C2	118.7 (5)	C33—C34—H34	119.1
C7—C2—C3	117.5 (6)	C29—C34—H34	119.1
C7—C2—C1	120.8 (5)	N3—C35—C36	127.3 (5)
C3—C2—C1	121.7 (6)	N3—C35—H35	116.4
C4—C3—C2	120.6 (6)	C36—C35—H35	116.4
C4—C3—H3	119.7	C37—C36—C41	119.9 (6)
C2—C3—H3	119.7	C37—C36—C35	122.5 (5)
C5—C4—C3	120.5 (6)	C41—C36—C35	117.6 (6)
C5—C4—H4	119.8	O5—C37—C36	123.8 (5)
C3—C4—H4	119.8	O5—C37—C38	118.1 (5)
C4—C5—C6	120.7 (6)	C36—C37—C38	118.0 (5)
C4—C5—Cl1	119.1 (6)	O6—C38—C39	124.7 (6)
C6—C5—Cl1	120.2 (6)	O6—C38—C37	114.5 (5)
C5—C6—C7	119.4 (6)	C39—C38—C37	120.8 (6)
C5—C6—H6	120.3	C38—C39—C40	120.5 (6)
C7—C6—H6	120.3	C38—C39—H39	119.7
C2—C7—C6	121.3 (6)	C40—C39—H39	119.7
C2—C7—H7	119.3	C41—C40—C39	120.6 (6)
C6—C7—H7	119.3	C41—C40—H40	119.7
N1—C8—C9	128.0 (5)	C39—C40—H40	119.7
N1—C8—H8	116.0	C40—C41—C36	120.1 (6)
C9—C8—H8	116.0	C40—C41—H41	119.9
C10—C9—C14	119.8 (5)	C36—C41—H41	119.9
C10—C9—C8	123.8 (5)	O6—C42—H42A	109.5
C14—C9—C8	116.4 (5)	O6—C42—H42B	109.5
O2—C10—C11	118.8 (5)	H42A—C42—H42B	109.5
O2—C10—C9	123.6 (5)	O6—C42—H42C	109.5
C11—C10—C9	117.6 (5)	H42A—C42—H42C	109.5
C12—C11—O3	124.7 (5)	H42B—C42—H42C	109.5
C12—C11—C10	121.0 (5)	C44—C43—C48	118.4 (6)
O3—C11—C10	114.3 (5)	C44—C43—Sn2	118.5 (4)
C11—C12—C13	120.5 (6)	C48—C43—Sn2	123.0 (5)
C11—C12—H12	119.7	C43—C44—C45	120.9 (6)
C13—C12—H12	119.7	C43—C44—H44	119.5
C14—C13—C12	120.1 (6)	C45—C44—H44	119.5
C14—C13—H13	120.0	C46—C45—C44	120.0 (7)
C12—C13—H13	120.0	C46—C45—H45	120.0
C13—C14—C9	121.0 (6)	C44—C45—H45	120.0
C13—C14—H14	119.5	C45—C46—C47	120.5 (7)
C9—C14—H14	119.5	C45—C46—H46	119.7
O3—C15—H15A	109.5	C47—C46—H46	119.7
O3—C15—H15B	109.5	C46—C47—C48	119.5 (7)
H15A—C15—H15B	109.5	C46—C47—H47	120.2
O3—C15—H15C	109.5	C48—C47—H47	120.2
H15A—C15—H15C	109.5	C43—C48—C47	120.6 (7)
H15B—C15—H15C	109.5	C43—C48—H48	119.7
C17—C16—C21	117.5 (5)	C47—C48—H48	119.7
C17—C16—Sn1	121.5 (4)	C50—C49—C54	117.4 (5)
C21—C16—Sn1	121.0 (4)	C50—C49—Sn2	121.0 (4)
C16—C17—C18	121.1 (6)	C54—C49—Sn2	121.3 (4)
C16—C17—H17	119.5	C49—C50—C51	121.3 (6)
C18—C17—H17	119.5	C49—C50—H50	119.3
C19—C18—C17	120.3 (6)	C51—C50—H50	119.3
C19—C18—H18	119.8	C52—C51—C50	119.9 (7)
C17—C18—H18	119.8	C52—C51—H51	120.1
C20—C19—C18	119.2 (6)	C50—C51—H51	120.1
C20—C19—H19	120.4	C51—C52—C53	120.3 (7)
C18—C19—H19	120.4	C51—C52—H52	119.8
C19—C20—C21	120.6 (6)	C53—C52—H52	119.8
C19—C20—H20	119.7	C52—C53—C54	120.0 (7)
C21—C20—H20	119.7	C52—C53—H53	120.0
C20—C21—C16	121.2 (6)	C54—C53—H53	120.0
C20—C21—H21	119.4	C53—C54—C49	121.0 (6)
C16—C21—H21	119.4	C53—C54—H54	119.5
C27—C22—C23	117.6 (5)	C49—C54—H54	119.5

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₂(C₁₅H₁₁ClN₂O₃)]
M_r	575.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	19.178 (2), 27.968 (3), 9.4230 (13)
β (°)	103.238 (2)
V (Å³)	4920.1 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.18
Crystal size (mm)	0.37 × 0.17 × 0.12

Data collection
Diffractometer	CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.670, 0.872
No. of measured, independent and observed [I > 2σ(I)] reflections	20342, 8658, 5197
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.087, 1.01
No. of reflections	8658
No. of parameters	615
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.76

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

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[4-Chloro-N'-(3-meth­oxy-2-oxidobenzyl­idene)benzohydrazidato]diphenyl­tin(IV)