Bis(5-methyl­pyrazine-2-carboxyl­ato)­diphenyl­tin(IV)

Gao, Z.

doi:10.1107/S1600536808016139

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page m867

doi:10.1107/S1600536808016139

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Bis(5-methylpyrazine-2-carboxylato)diphenyltin(IV)

Zhongjun Gao ^a ^*

^aDepartment of Chemistry, Jining University, Shandong 273155, People's Republic of China
^*Correspondence e-mail: zhongjungao@yahoo.cn

(Received 23 April 2008; accepted 28 May 2008; online 7 June 2008)

In the molecule of the title compound, [Sn(C₆H₅)₂(C₆H₅N₂O₂)₂], two O and one N atoms from the two 5-methylpyrazine-2-carboxylate ligands and one C atom of a phenyl group form a distorted square-planar arrangement in the equatorial plane around the Sn atom, while the distorted octahedral coordination is completed by an N atom of one of the 5-methylpyrazine-2-carboxylate ligands and a C atom of the other phenyl group in the axial positions. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For general background, see: Gielen et al. (1988 ). For related literature, see: Vollano et al. (1984 ); Ma et al. (2004 ).

Experimental

Crystal data

[Sn(C₆H₅)₂(C₆H₅N₂O₂)₂]
M_r = 547.13
Monoclinic, P 2₁ /n
a = 12.030 (4) Å
b = 14.658 (5) Å
c = 13.409 (5) Å
β = 91.872 (4)°
V = 2363.2 (14) Å³
Z = 4
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 298 (2) K
0.45 × 0.43 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.633, T_max = 0.824
12010 measured reflections
4166 independent reflections
2732 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.132
S = 1.05
4166 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—O1	2.086 (4)
Sn1—O3	2.091 (4)
Sn1—C13	2.117 (5)
Sn1—C19	2.130 (6)
Sn1—N1	2.357 (4)
Sn1—N3	2.363 (5)

O1—Sn1—O3	149.56 (15)
O1—Sn1—C13	97.14 (18)
O3—Sn1—C13	101.11 (18)
O1—Sn1—C19	101.5 (2)
O3—Sn1—C19	96.7 (2)
C13—Sn1—C19	105.6 (2)
O1—Sn1—N1	73.49 (15)
O3—Sn1—N1	82.40 (15)
C13—Sn1—N1	163.15 (18)
C19—Sn1—N1	90.17 (18)
O1—Sn1—N3	83.74 (16)
O3—Sn1—N3	73.16 (16)
C13—Sn1—N3	87.08 (18)
C19—Sn1—N3	165.3 (2)
N1—Sn1—N3	78.12 (15)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12C⋯O2ⁱ	0.96	2.51	3.315 (3)	142
C14—H14⋯O2ⁱ	0.93	2.57	3.298 (3)	135
Symmetry code: (i) -x, -y, -z+2.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016139/hk2458sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016139/hk2458Isup2.hkl

checkCIF report

Comment top

Self-assembled organotin derivatives of carboxylic acid ligands have been extensively studied due to their biological activities (Gielen et al., 1988). 5-methylpyrazine-2-carboxylic acid is a good bridging ligand that can sometimes be used to generate unexpected and interesting coordination polymers, and small changes in experimental conditions can lead to very different architectures (Ma et al., 2004).

The molecule of the title compound, (I), (Fig. 1) consists of two phenyl and two (5-methylpyrazine-2-carboxylate) groups bonded to the Sn atom and has a monomeric structure. The two O and the one N atoms of the two 2-methylpyrazine -5-carboxylate ligands and the one C atom of the one phenyl group in the equatorial plane around the Sn atom form a distorted square-planar arrangement, while the distorted octahedral coordination is completed by the one N atom of the one 5-methylpyrazine-2-carboxylate ligand and the one C atom of the other phenyl group in the axial positions (Table 1 and Fig. 1). The Sn1-O1 [2.086 (4) Å] and Sn1-O3 [2.091 (4) Å] bonds are much shorter than the van der Waal's sum of 4.0 Å (Vollano et al., 1984).

In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For general backgroud, see: Gielen et al. (1988). For related literature, see: Vollano et al. (1984); Ma et al. (2004).

Experimental top

For the preparation of the title compound, a mixture of diphenyltin dichloride (344 mg, 1.0 mmol), 5-methylpyrazine-2-carboxylic acid (276 mg, 2.0 mmol) and sodium ethoxide (136 mg, 2.0 mmol) in ethanol (80 ml) was heated under reflux for 12 h at 303 K. The resulting clear solution was evaporated under vacuum and the product recrystallized from a mixture of methanol to yield colorless, block-like crystals of (I) (yield; 377 mg, 69%, m.p. 459 K). Analysis, calculated for (I): C 52.68, H, 3.68; N 10.24%; found: C 52.96, H 3.87, N, 10.11%.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines.

Bis(5-methylpyrazine-2-carboxylato)diphenyltin(IV) top

Crystal data top

[Sn(C₆H₅)₂(C₆H₅N₂O₂)₂]	F(000) = 1096
M_r = 547.13	D_x = 1.538 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3659 reflections
a = 12.030 (4) Å	θ = 2.2–24.0°
b = 14.658 (5) Å	µ = 1.12 mm⁻¹
c = 13.409 (5) Å	T = 298 K
β = 91.872 (4)°	Block, colorless
V = 2363.2 (14) Å³	0.45 × 0.43 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4166 independent reflections
Radiation source: fine-focus sealed tube	2732 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→14
T_min = 0.633, T_max = 0.824	k = −17→14
12010 measured reflections	l = −15→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.066P)² + 2.0808P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4166 reflections	Δρ_max = 0.56 e Å⁻³
298 parameters	Δρ_min = −0.46 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

[Sn(C₆H₅)₂(C₆H₅N₂O₂)₂]	V = 2363.2 (14) Å³
M_r = 547.13	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.030 (4) Å	µ = 1.12 mm⁻¹
b = 14.658 (5) Å	T = 298 K
c = 13.409 (5) Å	0.45 × 0.43 × 0.18 mm
β = 91.872 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4166 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2732 reflections with I > 2σ(I)
T_min = 0.633, T_max = 0.824	R_int = 0.039
12010 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	298 parameters
wR(F²) = 0.132	H-atom parameters constrained
S = 1.05	Δρ_max = 0.56 e Å⁻³
4166 reflections	Δρ_min = −0.46 e Å⁻³

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Sn1	0.03995 (3)	0.25533 (2)	0.90574 (3)	0.04317 (17)
N1	0.0859 (4)	0.2891 (3)	1.0739 (3)	0.0440 (11)
N2	0.1584 (4)	0.3005 (4)	1.2707 (4)	0.0611 (13)
N3	−0.1259 (4)	0.2163 (3)	0.9852 (3)	0.0473 (11)
N4	−0.3408 (5)	0.1915 (4)	1.0421 (5)	0.0788 (17)
O1	0.0994 (3)	0.1346 (2)	0.9701 (3)	0.0517 (10)
O2	0.1706 (4)	0.0621 (3)	1.1024 (4)	0.0853 (15)
O3	−0.0532 (3)	0.3752 (2)	0.9163 (3)	0.0545 (10)
O4	−0.2151 (4)	0.4402 (3)	0.9433 (4)	0.0946 (16)
C1	0.1354 (5)	0.1303 (4)	1.0620 (5)	0.0557 (15)
C2	0.1298 (5)	0.2175 (4)	1.1213 (4)	0.0450 (13)
C3	0.1662 (5)	0.2249 (4)	1.2196 (5)	0.0556 (15)
H3	0.1976	0.1740	1.2509	0.067*
C4	0.1149 (5)	0.3732 (4)	1.2234 (4)	0.0541 (15)
C5	0.0804 (5)	0.3667 (4)	1.1242 (4)	0.0488 (14)
H5	0.0525	0.4184	1.0918	0.059*
C6	0.1053 (6)	0.4589 (4)	1.2806 (5)	0.082 (2)
H6A	0.1337	0.4496	1.3476	0.122*
H6B	0.0286	0.4767	1.2820	0.122*
H6C	0.1474	0.5060	1.2494	0.122*
C7	−0.1548 (5)	0.3744 (4)	0.9450 (5)	0.0570 (16)
C8	−0.1966 (5)	0.2842 (4)	0.9824 (4)	0.0513 (14)
C9	−0.3049 (6)	0.2725 (5)	1.0106 (6)	0.075 (2)
H9	−0.3537	0.3217	1.0078	0.090*
C10	−0.2715 (6)	0.1230 (5)	1.0447 (5)	0.0649 (18)
C11	−0.1606 (5)	0.1348 (4)	1.0159 (4)	0.0536 (15)
H11	−0.1117	0.0857	1.0183	0.064*
C12	−0.3116 (6)	0.0326 (5)	1.0790 (6)	0.091 (2)
H12A	−0.3885	0.0371	1.0953	0.136*
H12B	−0.2685	0.0138	1.1369	0.136*
H12C	−0.3037	−0.0115	1.0267	0.136*
C13	−0.0319 (4)	0.1966 (4)	0.7745 (4)	0.0469 (13)
C14	−0.0653 (5)	0.1070 (4)	0.7688 (5)	0.0665 (17)
H14	−0.0584	0.0704	0.8253	0.080*
C15	−0.1086 (6)	0.0704 (5)	0.6821 (6)	0.080 (2)
H15	−0.1298	0.0094	0.6801	0.096*
C16	−0.1207 (6)	0.1231 (7)	0.5990 (6)	0.088 (2)
H16	−0.1514	0.0983	0.5405	0.105*
C17	−0.0877 (6)	0.2125 (7)	0.6012 (5)	0.083 (2)
H17	−0.0953	0.2487	0.5444	0.100*
C18	−0.0427 (5)	0.2482 (4)	0.6896 (5)	0.0645 (18)
H18	−0.0194	0.3087	0.6911	0.077*
C19	0.1901 (5)	0.3181 (4)	0.8612 (4)	0.0556 (15)
C20	0.2684 (7)	0.2621 (5)	0.8185 (7)	0.084 (2)
H20	0.2541	0.1998	0.8142	0.101*
C21	0.3653 (7)	0.2945 (8)	0.7828 (7)	0.111 (3)
H21	0.4156	0.2557	0.7529	0.134*
C22	0.3867 (8)	0.3866 (7)	0.7921 (6)	0.104 (2)
H22	0.4537	0.4096	0.7701	0.124*
C23	0.3137 (7)	0.4438 (6)	0.8320 (6)	0.090 (2)
H23	0.3286	0.5060	0.8365	0.108*
C24	0.2133 (6)	0.4077 (5)	0.8671 (5)	0.0750 (19)
H24	0.1620	0.4469	0.8950	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0388 (2)	0.0483 (3)	0.0423 (2)	0.00011 (17)	−0.00113 (16)	0.00171 (17)
N1	0.040 (3)	0.046 (2)	0.046 (3)	−0.006 (2)	0.001 (2)	0.003 (2)
N2	0.058 (3)	0.075 (4)	0.050 (3)	−0.005 (3)	−0.006 (2)	0.004 (3)
N3	0.045 (3)	0.049 (3)	0.048 (3)	0.000 (2)	−0.001 (2)	−0.003 (2)
N4	0.068 (4)	0.081 (4)	0.090 (4)	0.002 (3)	0.025 (3)	−0.005 (3)
O1	0.054 (2)	0.047 (2)	0.055 (2)	0.0109 (17)	−0.0018 (19)	−0.0026 (17)
O2	0.121 (4)	0.052 (3)	0.081 (3)	0.018 (3)	−0.015 (3)	0.012 (2)
O3	0.058 (3)	0.046 (2)	0.059 (2)	0.0037 (18)	−0.009 (2)	0.0066 (17)
O4	0.080 (4)	0.067 (3)	0.136 (5)	0.030 (3)	0.001 (3)	0.006 (3)
C1	0.051 (4)	0.053 (4)	0.063 (4)	0.004 (3)	−0.005 (3)	0.011 (3)
C2	0.044 (3)	0.049 (3)	0.042 (3)	−0.003 (3)	0.002 (3)	0.006 (3)
C3	0.051 (4)	0.063 (4)	0.052 (4)	0.000 (3)	−0.006 (3)	0.011 (3)
C4	0.053 (4)	0.063 (4)	0.046 (3)	−0.008 (3)	−0.003 (3)	−0.006 (3)
C5	0.044 (3)	0.048 (3)	0.053 (3)	−0.004 (2)	−0.001 (3)	0.000 (3)
C6	0.096 (6)	0.081 (5)	0.068 (5)	−0.004 (4)	−0.004 (4)	−0.023 (4)
C7	0.053 (4)	0.057 (4)	0.061 (4)	0.015 (3)	−0.005 (3)	−0.003 (3)
C8	0.044 (4)	0.059 (3)	0.051 (3)	0.007 (3)	0.004 (3)	−0.015 (3)
C9	0.060 (5)	0.080 (5)	0.085 (5)	0.023 (4)	0.008 (4)	−0.003 (4)
C10	0.064 (5)	0.075 (5)	0.057 (4)	−0.014 (4)	0.018 (3)	−0.013 (3)
C11	0.054 (4)	0.053 (4)	0.055 (4)	−0.003 (3)	0.009 (3)	−0.005 (3)
C12	0.087 (6)	0.098 (6)	0.090 (6)	−0.033 (4)	0.032 (4)	0.002 (4)
C13	0.039 (3)	0.057 (4)	0.045 (3)	−0.005 (3)	−0.001 (3)	−0.003 (3)
C14	0.065 (4)	0.065 (4)	0.069 (4)	−0.005 (3)	−0.015 (3)	−0.007 (3)
C15	0.074 (5)	0.071 (5)	0.095 (6)	−0.006 (4)	−0.017 (4)	−0.027 (4)
C16	0.059 (5)	0.132 (8)	0.072 (5)	−0.004 (5)	−0.004 (4)	−0.036 (5)
C17	0.062 (5)	0.143 (7)	0.044 (4)	−0.010 (5)	−0.001 (3)	0.004 (4)
C18	0.051 (4)	0.095 (5)	0.047 (4)	−0.015 (3)	0.002 (3)	0.006 (3)
C19	0.051 (3)	0.066 (4)	0.050 (3)	−0.007 (3)	−0.001 (3)	0.001 (3)
C20	0.069 (5)	0.089 (5)	0.095 (5)	−0.006 (4)	0.026 (4)	0.003 (4)
C21	0.077 (5)	0.147 (6)	0.112 (6)	−0.008 (5)	0.042 (4)	−0.001 (5)
C22	0.082 (5)	0.130 (6)	0.099 (5)	−0.030 (5)	0.015 (4)	0.003 (5)
C23	0.097 (5)	0.096 (5)	0.077 (5)	−0.038 (4)	0.006 (4)	0.002 (4)
C24	0.073 (4)	0.089 (5)	0.063 (4)	−0.023 (4)	0.003 (3)	0.007 (3)

Geometric parameters (Å, º) top

Sn1—O1	2.086 (4)	C9—H9	0.9300
Sn1—O3	2.091 (4)	C10—C11	1.411 (8)
Sn1—C13	2.117 (5)	C10—C12	1.488 (9)
Sn1—C19	2.130 (6)	C11—H11	0.9300
Sn1—N1	2.357 (4)	C12—H12A	0.9600
Sn1—N3	2.363 (5)	C12—H12B	0.9600
N1—C5	1.324 (7)	C12—H12C	0.9600
N1—C2	1.328 (7)	C13—C18	1.370 (8)
N2—C3	1.308 (8)	C13—C14	1.375 (8)
N2—C4	1.338 (7)	C14—C15	1.368 (9)
N3—C8	1.309 (7)	C14—H14	0.9300
N3—C11	1.335 (7)	C15—C16	1.360 (10)
N4—C10	1.305 (8)	C15—H15	0.9300
N4—C9	1.336 (9)	C16—C17	1.370 (10)
O1—C1	1.294 (7)	C16—H16	0.9300
O2—C1	1.207 (6)	C17—C18	1.389 (10)
O3—C7	1.292 (7)	C17—H17	0.9300
O4—C7	1.207 (7)	C18—H18	0.9300
C1—C2	1.508 (8)	C19—C24	1.344 (9)
C2—C3	1.379 (8)	C19—C20	1.387 (9)
C3—H3	0.9300	C20—C21	1.361 (11)
C4—C5	1.384 (7)	C20—H20	0.9300
C4—C6	1.477 (8)	C21—C22	1.380 (12)
C5—H5	0.9300	C21—H21	0.9300
C6—H6A	0.9600	C22—C23	1.339 (11)
C6—H6B	0.9600	C22—H22	0.9300
C6—H6C	0.9600	C23—C24	1.413 (9)
C7—C8	1.506 (9)	C23—H23	0.9300
C8—C9	1.379 (9)	C24—H24	0.9300

O1—Sn1—O3	149.56 (15)	N4—C9—C8	121.0 (6)
O1—Sn1—C13	97.14 (18)	N4—C9—H9	119.5
O3—Sn1—C13	101.11 (18)	C8—C9—H9	119.5
O1—Sn1—C19	101.5 (2)	N4—C10—C11	120.5 (6)
O3—Sn1—C19	96.7 (2)	N4—C10—C12	118.7 (6)
C13—Sn1—C19	105.6 (2)	C11—C10—C12	120.8 (6)
O1—Sn1—N1	73.49 (15)	N3—C11—C10	120.2 (6)
O3—Sn1—N1	82.40 (15)	N3—C11—H11	119.9
C13—Sn1—N1	163.15 (18)	C10—C11—H11	119.9
C19—Sn1—N1	90.17 (18)	C10—C12—H12A	109.5
O1—Sn1—N3	83.74 (16)	C10—C12—H12B	109.5
O3—Sn1—N3	73.16 (16)	H12A—C12—H12B	109.5
C13—Sn1—N3	87.08 (18)	C10—C12—H12C	109.5
C19—Sn1—N3	165.3 (2)	H12A—C12—H12C	109.5
N1—Sn1—N3	78.12 (15)	H12B—C12—H12C	109.5
C5—N1—C2	117.4 (5)	C18—C13—C14	117.5 (6)
C5—N1—Sn1	130.8 (4)	C18—C13—Sn1	119.5 (4)
C2—N1—Sn1	111.6 (4)	C14—C13—Sn1	123.0 (4)
C3—N2—C4	117.5 (5)	C15—C14—C13	121.7 (7)
C8—N3—C11	118.7 (5)	C15—C14—H14	119.2
C8—N3—Sn1	111.1 (4)	C13—C14—H14	119.2
C11—N3—Sn1	129.3 (4)	C16—C15—C14	120.1 (7)
C10—N4—C9	118.7 (6)	C16—C15—H15	119.9
C1—O1—Sn1	122.3 (3)	C14—C15—H15	119.9
C7—O3—Sn1	121.8 (3)	C15—C16—C17	120.2 (7)
O2—C1—O1	124.7 (6)	C15—C16—H16	119.9
O2—C1—C2	119.0 (6)	C17—C16—H16	119.9
O1—C1—C2	116.2 (5)	C16—C17—C18	118.9 (7)
N1—C2—C3	120.2 (5)	C16—C17—H17	120.5
N1—C2—C1	116.2 (5)	C18—C17—H17	120.5
C3—C2—C1	123.5 (5)	C13—C18—C17	121.7 (7)
N2—C3—C2	122.7 (6)	C13—C18—H18	119.2
N2—C3—H3	118.6	C17—C18—H18	119.2
C2—C3—H3	118.6	C24—C19—C20	117.4 (6)
N2—C4—C5	120.0 (5)	C24—C19—Sn1	125.6 (5)
N2—C4—C6	117.9 (5)	C20—C19—Sn1	116.9 (5)
C5—C4—C6	122.1 (6)	C21—C20—C19	122.6 (8)
N1—C5—C4	122.0 (5)	C21—C20—H20	118.7
N1—C5—H5	119.0	C19—C20—H20	118.7
C4—C5—H5	119.0	C20—C21—C22	118.0 (9)
C4—C6—H6A	109.5	C20—C21—H21	121.0
C4—C6—H6B	109.5	C22—C21—H21	121.0
H6A—C6—H6B	109.5	C23—C22—C21	121.8 (9)
C4—C6—H6C	109.5	C23—C22—H22	119.1
H6A—C6—H6C	109.5	C21—C22—H22	119.1
H6B—C6—H6C	109.5	C22—C23—C24	118.5 (8)
O4—C7—O3	124.2 (6)	C22—C23—H23	120.7
O4—C7—C8	120.0 (6)	C24—C23—H23	120.7
O3—C7—C8	115.9 (5)	C19—C24—C23	121.6 (7)
N3—C8—C9	121.1 (6)	C19—C24—H24	119.2
N3—C8—C7	116.9 (5)	C23—C24—H24	119.2
C9—C8—C7	122.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···O2ⁱ	0.96	2.51	3.315 (3)	142
C14—H14···O2ⁱ	0.93	2.57	3.298 (3)	135

Symmetry code: (i) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₂(C₆H₅N₂O₂)₂]
M_r	547.13
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	12.030 (4), 14.658 (5), 13.409 (5)
β (°)	91.872 (4)
V (Å³)	2363.2 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.45 × 0.43 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.633, 0.824
No. of measured, independent and observed [I > 2σ(I)] reflections	12010, 4166, 2732
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.132, 1.05
No. of reflections	4166
No. of parameters	298
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.46

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Sn1—O1	2.086 (4)	Sn1—C19	2.130 (6)
Sn1—O3	2.091 (4)	Sn1—N1	2.357 (4)
Sn1—C13	2.117 (5)	Sn1—N3	2.363 (5)

O1—Sn1—O3	149.56 (15)	C13—Sn1—N1	163.15 (18)
O1—Sn1—C13	97.14 (18)	C19—Sn1—N1	90.17 (18)
O3—Sn1—C13	101.11 (18)	O1—Sn1—N3	83.74 (16)
O1—Sn1—C19	101.5 (2)	O3—Sn1—N3	73.16 (16)
O3—Sn1—C19	96.7 (2)	C13—Sn1—N3	87.08 (18)
C13—Sn1—C19	105.6 (2)	C19—Sn1—N3	165.3 (2)
O1—Sn1—N1	73.49 (15)	N1—Sn1—N3	78.12 (15)
O3—Sn1—N1	82.40 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···O2ⁱ	0.96	2.51	3.315 (3)	142.00
C14—H14···O2ⁱ	0.93	2.57	3.298 (3)	135.00

Symmetry code: (i) −x, −y, −z+2.

Acknowledgements

We acknowledge the financial support of the Science Foundation of Shandong.

References

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