Bis(5-methyl-pyrazine-2-carboxyl-ato)-diphenyl-tin(IV).

In the mol-ecule of the title compound, [Sn(C(6)H(5))(2)(C(6)H(5)N(2)O(2))(2)], two O and one N atoms from the two 5-methyl-pyrazine-2-carboxyl-ate 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 octa-hedral coordination is completed by an N atom of one of the 5-methyl-pyrazine-2-carboxyl-ate ligands and a C atom of the other phenyl group in the axial positions. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules 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 = 547.13

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.132

S = 1.05

4166 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.46 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Sn(C6H5)2(C6H5N2O2)2]	F000 = 1096
Mr = 547.13	Dx = 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 = 2.2–24.0º
b = 14.658 (5) Å	µ = 1.12 mm−1
c = 13.409 (5) Å	T = 298 (2) K
β = 91.872 (4)º	Block, colorless
V = 2363.2 (14) Å3	0.45 × 0.43 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4166 independent reflections
Radiation source: fine-focus sealed tube	2732 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −12→14
Tmin = 0.633, Tmax = 0.824	k = −17→14
12010 measured reflections	l = −15→15

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(Fo2) + (0.066P)2 + 2.0808P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4166 reflections	Δρmax = 0.56 e Å−3
298 parameters	Δρmin = −0.46 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .