(Methanol-κO)(2-methyl-3,5-dinitro-benzoato-κO)triphenyl-tin(IV).

In the title complex, [Sn(C(6)H(5))(3)(C(8)H(5)N(2)O(6))(CH(3)OH)], the Sn(IV) ion is coordinated in a slightly distorted trigonal-bipyramidal geometry by three phenyl ligands in the equatorial plane and by a 2-methyl-3,5-dinitro-benzene-carboxyl-ato ligand and a methanol ligand at the apical sites. In the crystal, complex mol-ecules are linked via inter-molecular O-H⋯O hydrogen bonds, forming chains along [100].

Related literature

For the crystal structures of two triphenyl­tin complexes with a 2,3-dinitro­benzoate ligand, see: Azir-ur-Rehman et al. (2006 ▶); Win et al. (2006 ▶). For the structure of a tin complex with a 2-methyl­benzoate ligand, see: Danish et al. (2010) ▶. For applications of organotin compounds, see: Reisi et al. (2006 ▶).

Experimental

Crystal data

[Sn(C6H5)3(C8H5N2O6)(CH4O)]

M = 607.17

Monoclinic,

a = 8.0597 (16) Å

b = 20.094 (4) Å

c = 16.022 (3) Å

β = 95.29 (3)°

V = 2583.8 (9) Å3

Z = 4

Mo Kα radiation

μ = 1.04 mm−1

T = 293 K

0.31 × 0.23 × 0.07 mm

Data collection

Kuma KM4 four-circle diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008) ▶ T min = 0.842, T max = 0.930

6387 measured reflections

6141 independent reflections

3440 reflections with I > 2σ(I)

R int = 0.024

3 standard reflections every 200 reflections intensity decay: 7.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.133

S = 1.04

6141 reflections

340 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.96 e Å−3

Δρmin = −0.78 e Å−3

Data collection: KM-4 Software (Kuma, 1996 ▶); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2001 ▶); 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/S1600536811011184/lh5223sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011184/lh5223Isup2.hkl

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

[Sn(C6H5)3(C8H5N2O6)(CH4O)]	F(000) = 1224
Mr = 607.17	Dx = 1.561 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 8.0597 (16) Å	θ = 6–15°
b = 20.094 (4) Å	µ = 1.04 mm−1
c = 16.022 (3) Å	T = 293 K
β = 95.29 (3)°	Plates, pale yellow
V = 2583.8 (9) Å3	0.31 × 0.23 × 0.07 mm
Z = 4

Kuma KM4 four-circle diffractometer	3440 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 28.5°, θmin = 1.6°
profile data from ω/2θ scans	h = −10→10
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	k = 0→26
Tmin = 0.842, Tmax = 0.930	l = −20→0
6387 measured reflections	3 standard reflections every 200 reflections
6141 independent reflections	intensity decay: 7.5%

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0654P)2 + 3.2267P] where P = (Fo2 + 2Fc2)/3
6141 reflections	(Δ/σ)max < 0.001
340 parameters	Δρmax = 0.96 e Å−3
1 restraint	Δρmin = −0.78 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.47331 (3)	0.246055 (14)	0.773898 (18)	0.03309 (10)
O11	0.2416 (4)	0.30063 (18)	0.7557 (2)	0.0474 (8)
C36	0.6404 (6)	0.2620 (3)	0.6100 (3)	0.0451 (11)
H36	0.6976	0.2237	0.6283	0.054*
C11	−0.0109 (5)	0.3536 (2)	0.7691 (3)	0.0333 (9)
C12	−0.0853 (6)	0.3849 (2)	0.8344 (3)	0.0373 (10)
C21	0.5163 (6)	0.2838 (2)	0.8981 (3)	0.0383 (10)
C31	0.5350 (5)	0.2938 (2)	0.6620 (3)	0.0350 (9)
C15	−0.1386 (7)	0.4289 (2)	0.6689 (3)	0.0443 (11)
O12	0.0567 (5)	0.24487 (18)	0.8209 (3)	0.0659 (12)
N12	−0.1578 (8)	0.4552 (3)	0.5823 (3)	0.0647 (14)
C41	0.3905 (5)	0.1462 (2)	0.7589 (3)	0.0372 (10)
C16	−0.0334 (6)	0.3769 (2)	0.6871 (3)	0.0396 (10)
H16	0.0228	0.3573	0.6454	0.047*
C42	0.3836 (7)	0.1148 (3)	0.6825 (3)	0.0498 (12)
H42	0.4173	0.1376	0.6364	0.060*
C13	−0.1887 (6)	0.4382 (2)	0.8096 (3)	0.0425 (11)
C18	0.1024 (5)	0.2939 (2)	0.7841 (3)	0.0358 (9)
C32	0.4572 (7)	0.3511 (3)	0.6343 (4)	0.0520 (13)
H32	0.3903	0.3736	0.6693	0.062*
C14	−0.2212 (6)	0.4600 (2)	0.7284 (4)	0.0472 (12)
H14	−0.2960	0.4944	0.7147	0.057*
N11	−0.2681 (6)	0.4779 (2)	0.8730 (4)	0.0592 (13)
C34	0.5750 (8)	0.3438 (4)	0.5043 (4)	0.0663 (18)
H34	0.5852	0.3600	0.4506	0.080*
C26	0.4510 (7)	0.3445 (3)	0.9175 (4)	0.0602 (15)
H26	0.3961	0.3704	0.8756	0.072*
C25	0.4669 (9)	0.3670 (4)	0.9993 (5)	0.080 (2)
H25	0.4226	0.4082	1.0117	0.096*
C22	0.5990 (7)	0.2460 (3)	0.9619 (3)	0.0532 (12)
H22	0.6448	0.2050	0.9500	0.064*
C33	0.4755 (8)	0.3764 (3)	0.5555 (4)	0.0615 (16)
H33	0.4205	0.4152	0.5375	0.074*
C45	0.2907 (8)	0.0463 (3)	0.8180 (5)	0.0641 (16)
H45	0.2612	0.0229	0.8645	0.077*
C35	0.6596 (7)	0.2877 (3)	0.5310 (4)	0.0573 (15)
H35	0.7300	0.2668	0.4964	0.069*
C44	0.2799 (8)	0.0158 (3)	0.7412 (5)	0.0673 (18)
H44	0.2407	−0.0276	0.7356	0.081*
C46	0.3443 (7)	0.1107 (3)	0.8273 (4)	0.0543 (14)
H46	0.3498	0.1307	0.8798	0.065*
O16	−0.0735 (7)	0.4294 (3)	0.5316 (3)	0.0816 (15)
C17	−0.0513 (7)	0.3627 (3)	0.9229 (3)	0.0569 (14)
H171	−0.0159	0.3170	0.9241	0.085*
H172	−0.1509	0.3668	0.9511	0.085*
H173	0.0349	0.3898	0.9507	0.085*
C43	0.3267 (8)	0.0492 (3)	0.6729 (4)	0.0649 (17)
H43	0.3209	0.0286	0.6207	0.078*
O14	−0.4095 (6)	0.4972 (3)	0.8526 (4)	0.0997 (18)
O13	−0.1901 (7)	0.4907 (3)	0.9382 (4)	0.0993 (19)
O15	−0.2542 (8)	0.5001 (3)	0.5664 (3)	0.0948 (18)
C23	0.6126 (9)	0.2701 (4)	1.0438 (4)	0.073 (2)
H23	0.6677	0.2451	1.0866	0.088*
C24	0.5455 (9)	0.3303 (5)	1.0615 (4)	0.084 (3)
H24	0.5540	0.3460	1.1163	0.101*
O51	0.7475 (4)	0.19935 (17)	0.7928 (3)	0.0485 (9)
C51	0.7965 (8)	0.1327 (3)	0.7876 (5)	0.079 (2)
H51A	0.7885	0.1113	0.8406	0.118*
H51B	0.9096	0.1307	0.7734	0.118*
H51C	0.7251	0.1104	0.7452	0.118*
H51	0.825 (7)	0.223 (3)	0.808 (5)	0.10 (3)*

	U11	U22	U33	U12	U13	U23
Sn1	0.03123 (15)	0.03696 (16)	0.03213 (15)	0.00077 (14)	0.00859 (10)	0.00146 (15)
O11	0.0307 (17)	0.060 (2)	0.053 (2)	0.0075 (15)	0.0130 (15)	0.0109 (17)
C36	0.038 (2)	0.055 (3)	0.043 (3)	0.000 (2)	0.009 (2)	−0.003 (2)
C11	0.026 (2)	0.040 (2)	0.035 (2)	0.0011 (17)	0.0071 (17)	0.0017 (19)
C12	0.031 (2)	0.040 (2)	0.041 (3)	−0.0014 (18)	0.0049 (19)	0.000 (2)
C21	0.036 (2)	0.040 (2)	0.040 (3)	−0.0054 (19)	0.0093 (19)	0.002 (2)
C31	0.029 (2)	0.041 (2)	0.036 (2)	−0.0016 (18)	0.0059 (18)	−0.0010 (19)
C15	0.053 (3)	0.036 (2)	0.041 (3)	−0.007 (2)	−0.008 (2)	0.006 (2)
O12	0.046 (2)	0.051 (2)	0.105 (4)	0.0119 (17)	0.028 (2)	0.029 (2)
N12	0.088 (4)	0.049 (3)	0.055 (3)	−0.005 (3)	−0.011 (3)	0.012 (2)
C41	0.030 (2)	0.040 (2)	0.042 (3)	0.0010 (18)	0.0029 (19)	−0.001 (2)
C16	0.038 (2)	0.048 (3)	0.033 (2)	−0.002 (2)	0.004 (2)	0.001 (2)
C42	0.050 (3)	0.054 (3)	0.044 (3)	0.002 (2)	−0.004 (2)	−0.001 (2)
C13	0.037 (3)	0.040 (2)	0.051 (3)	0.0043 (19)	0.007 (2)	−0.005 (2)
C18	0.031 (2)	0.038 (2)	0.039 (2)	0.0019 (17)	0.0076 (18)	−0.0009 (19)
C32	0.047 (3)	0.055 (3)	0.058 (3)	0.004 (2)	0.019 (3)	0.015 (3)
C14	0.045 (3)	0.034 (2)	0.062 (4)	0.006 (2)	−0.005 (2)	0.006 (2)
N11	0.056 (3)	0.051 (3)	0.072 (4)	0.012 (2)	0.016 (3)	−0.012 (2)
C34	0.065 (4)	0.097 (5)	0.038 (3)	−0.014 (4)	0.008 (3)	0.019 (3)
C26	0.054 (3)	0.059 (3)	0.067 (4)	0.006 (3)	0.004 (3)	−0.015 (3)
C25	0.063 (4)	0.096 (5)	0.084 (5)	−0.007 (4)	0.015 (4)	−0.057 (5)
C22	0.050 (3)	0.063 (3)	0.047 (3)	−0.002 (3)	0.004 (2)	0.001 (3)
C33	0.057 (3)	0.074 (4)	0.055 (4)	0.001 (3)	0.008 (3)	0.029 (3)
C45	0.069 (4)	0.048 (3)	0.078 (4)	−0.010 (3)	0.015 (3)	0.012 (3)
C35	0.054 (3)	0.082 (4)	0.039 (3)	−0.012 (3)	0.019 (2)	−0.010 (3)
C44	0.063 (4)	0.037 (3)	0.098 (5)	−0.005 (3)	−0.015 (4)	0.000 (3)
C46	0.061 (3)	0.049 (3)	0.055 (3)	−0.004 (3)	0.021 (3)	0.000 (3)
O16	0.120 (4)	0.082 (3)	0.044 (2)	−0.004 (3)	0.010 (3)	0.013 (2)
C17	0.058 (3)	0.070 (4)	0.043 (3)	0.008 (3)	0.011 (3)	0.006 (3)
C43	0.075 (4)	0.052 (3)	0.063 (4)	0.004 (3)	−0.020 (3)	−0.016 (3)
O14	0.070 (3)	0.119 (4)	0.112 (4)	0.052 (3)	0.019 (3)	−0.014 (4)
O13	0.104 (4)	0.118 (4)	0.076 (4)	0.029 (3)	0.009 (3)	−0.039 (3)
O15	0.135 (5)	0.069 (3)	0.074 (3)	0.019 (3)	−0.026 (3)	0.026 (3)
C23	0.063 (4)	0.113 (6)	0.042 (3)	−0.027 (4)	−0.003 (3)	0.004 (3)
C24	0.060 (4)	0.148 (8)	0.044 (4)	−0.026 (5)	0.008 (3)	−0.033 (4)
O51	0.0348 (19)	0.0401 (18)	0.071 (3)	0.0065 (15)	0.0049 (18)	−0.0007 (18)
C51	0.060 (4)	0.045 (3)	0.129 (7)	0.015 (3)	−0.006 (4)	−0.011 (4)

Sn1—C41	2.121 (5)	C14—H14	0.9300
Sn1—C21	2.128 (5)	N11—O13	1.196 (7)
Sn1—C31	2.132 (5)	N11—O14	1.219 (6)
Sn1—O11	2.162 (3)	C34—C35	1.366 (9)
Sn1—O51	2.394 (3)	C34—C33	1.366 (9)
O11—C18	1.257 (5)	C34—H34	0.9300
C36—C35	1.389 (8)	C26—C25	1.380 (9)
C36—C31	1.397 (6)	C26—H26	0.9300
C36—H36	0.9300	C25—C24	1.351 (11)
C11—C16	1.391 (6)	C25—H25	0.9300
C11—C12	1.400 (6)	C22—C23	1.394 (9)
C11—C18	1.514 (6)	C22—H22	0.9300
C12—C13	1.393 (6)	C33—H33	0.9300
C12—C17	1.489 (7)	C45—C44	1.369 (9)
C21—C26	1.376 (7)	C45—C46	1.367 (8)
C21—C22	1.393 (7)	C45—H45	0.9300
C31—C32	1.365 (7)	C35—H35	0.9300
C15—C16	1.360 (7)	C44—C43	1.367 (10)
C15—C14	1.364 (8)	C44—H44	0.9300
C15—N12	1.479 (7)	C46—H46	0.9300
O12—C18	1.222 (6)	C17—H171	0.9600
N12—O15	1.203 (7)	C17—H172	0.9600
N12—O16	1.221 (7)	C17—H173	0.9600
C41—C42	1.374 (7)	C43—H43	0.9300
C41—C46	1.387 (7)	C23—C24	1.364 (11)
C16—H16	0.9300	C23—H23	0.9300
C42—C43	1.400 (8)	C24—H24	0.9300
C42—H42	0.9300	O51—C51	1.401 (6)
C13—C14	1.374 (7)	O51—H51	0.81 (2)
C13—N11	1.482 (7)	C51—H51A	0.9600
C32—C33	1.382 (7)	C51—H51B	0.9600
C32—H32	0.9300	C51—H51C	0.9600
C41—Sn1—C21	117.76 (18)	O13—N11—C13	119.3 (5)
C41—Sn1—C31	115.18 (18)	O14—N11—C13	116.1 (5)
C21—Sn1—C31	126.54 (17)	C35—C34—C33	120.7 (5)
C41—Sn1—O11	101.88 (15)	C35—C34—H34	119.7
C21—Sn1—O11	90.55 (17)	C33—C34—H34	119.7
C31—Sn1—O11	85.63 (15)	C21—C26—C25	120.1 (7)
C41—Sn1—O51	85.44 (15)	C21—C26—H26	120.0
C21—Sn1—O51	87.29 (17)	C25—C26—H26	120.0
C31—Sn1—O51	89.91 (15)	C24—C25—C26	121.2 (7)
O11—Sn1—O51	172.54 (13)	C24—C25—H25	119.4
C18—O11—Sn1	133.3 (3)	C26—C25—H25	119.4
C35—C36—C31	119.9 (5)	C21—C22—C23	119.5 (6)
C35—C36—H36	120.1	C21—C22—H22	120.3
C31—C36—H36	120.1	C23—C22—H22	120.3
C16—C11—C12	121.7 (4)	C34—C33—C32	119.4 (6)
C16—C11—C18	116.1 (4)	C34—C33—H33	120.3
C12—C11—C18	122.1 (4)	C32—C33—H33	120.3
C13—C12—C11	114.8 (4)	C44—C45—C46	120.9 (6)
C13—C12—C17	123.7 (5)	C44—C45—H45	119.5
C11—C12—C17	121.5 (4)	C46—C45—H45	119.5
C26—C21—C22	119.0 (5)	C34—C35—C36	119.9 (6)
C26—C21—Sn1	119.7 (4)	C34—C35—H35	120.0
C22—C21—Sn1	121.2 (4)	C36—C35—H35	120.0
C32—C31—C36	118.6 (5)	C43—C44—C45	120.0 (5)
C32—C31—Sn1	121.1 (4)	C43—C44—H44	120.0
C36—C31—Sn1	119.8 (3)	C45—C44—H44	120.0
C16—C15—C14	122.4 (5)	C45—C46—C41	120.4 (6)
C16—C15—N12	119.0 (5)	C45—C46—H46	119.8
C14—C15—N12	118.5 (5)	C41—C46—H46	119.8
O15—N12—O16	124.5 (6)	C12—C17—H171	109.5
O15—N12—C15	118.4 (6)	C12—C17—H172	109.5
O16—N12—C15	117.1 (5)	H171—C17—H172	109.5
C42—C41—C46	118.4 (5)	C12—C17—H173	109.5
C42—C41—Sn1	121.4 (4)	H171—C17—H173	109.5
C46—C41—Sn1	120.1 (4)	H172—C17—H173	109.5
C15—C16—C11	119.1 (5)	C44—C43—C42	119.1 (6)
C15—C16—H16	120.5	C44—C43—H43	120.4
C11—C16—H16	120.5	C42—C43—H43	120.4
C41—C42—C43	121.1 (6)	C24—C23—C22	120.3 (7)
C41—C42—H42	119.5	C24—C23—H23	119.8
C43—C42—H42	119.5	C22—C23—H23	119.8
C14—C13—C12	124.8 (5)	C25—C24—C23	119.9 (6)
C14—C13—N11	114.9 (5)	C25—C24—H24	120.0
C12—C13—N11	120.2 (5)	C23—C24—H24	120.0
O12—C18—O11	125.5 (4)	C51—O51—Sn1	129.0 (4)
O12—C18—C11	120.7 (4)	C51—O51—H51	112 (6)
O11—C18—C11	113.8 (4)	Sn1—O51—H51	119 (6)
C31—C32—C33	121.5 (5)	O51—C51—H51A	109.5
C31—C32—H32	119.3	O51—C51—H51B	109.5
C33—C32—H32	119.3	H51A—C51—H51B	109.5
C15—C14—C13	117.0 (4)	O51—C51—H51C	109.5
C15—C14—H14	121.5	H51A—C51—H51C	109.5
C13—C14—H14	121.5	H51B—C51—H51C	109.5
O13—N11—O14	124.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O51—H51···O12i	0.81 (2)	1.91 (4)	2.654 (6)	153 (8)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O51—H51⋯O12i	0.81 (2)	1.91 (4)	2.654 (6)	153 (8)

Symmetry code: (i) .