(Methanol-κO)(2-methyl-3-nitro-benzoato-κO)triphenyl-tin(IV).

The five-coordinate Sn atom in the title compound, [Sn(C(6)H(5))(3)(C(8)H(6)NO(4))(CH(3)OH)], exists in a trans-C(3)SnO(2) trigonal-bipyramidal coordination polyhedron of which the O atoms of the methanol mol-ecule and carboxyl-ate group occupy the apical sites. In the crystal, adjacent mol-ecules are linked by inter-molecular O-H⋯O inter-actions, generating a helical hydrogen-bonded chain running along the b axis.

Related literature

For other methanol/ethanol-coordinated triphenyl­tin carboxyl­ates, see: Alcock & Roe (1989 ▶); Gao et al. (2006 ▶); Lo & Ng (2009 ▶); Ma et al. (2004 ▶); Ng (1998 ▶, 1999 ▶); Wang et al. (2007 ▶); Yeap & Teoh (2003 ▶); Yin et al. (2002 ▶).

Experimental

Crystal data

[Sn(C6H5)3(C8H6NO4)(CH4O)]

M = 562.17

Monoclinic,

a = 10.8385 (13) Å

b = 14.8791 (18) Å

c = 15.8243 (19) Å

β = 94.004 (2)°

V = 2545.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.04 mm−1

T = 293 K

0.40 × 0.25 × 0.10 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.681, T max = 0.903

15231 measured reflections

5739 independent reflections

4515 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 1.08

5739 reflections

313 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.15 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033623/bt5330sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033623/bt5330Isup2.hkl

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

[Sn(C6H5)3(C8H6NO4)(CH4O)]	F(000) = 1136
Mr = 562.17	Dx = 1.467 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 918 reflections
a = 10.8385 (13) Å	θ = 2.7–25.1°
b = 14.8791 (18) Å	µ = 1.04 mm−1
c = 15.8243 (19) Å	T = 293 K
β = 94.004 (2)°	Block, yellow
V = 2545.7 (5) Å3	0.40 × 0.25 × 0.10 mm
Z = 4

Bruker SMART diffractometer	5739 independent reflections
Radiation source: fine-focus sealed tube	4515 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
Tmin = 0.681, Tmax = 0.903	k = −18→19
15231 measured reflections	l = −20→10

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0581P)2 + 1.4418P] where P = (Fo2 + 2Fc2)/3
5739 reflections	(Δ/σ)max = 0.001
313 parameters	Δρmax = 1.15 e Å−3
1 restraint	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
Sn1	0.63268 (2)	0.197738 (16)	0.687848 (16)	0.04465 (10)
O1	0.6379 (3)	0.32447 (16)	0.62345 (18)	0.0566 (7)
O2	0.7358 (3)	0.40787 (19)	0.72344 (18)	0.0635 (7)
O3	0.7290 (6)	0.5035 (5)	0.3367 (3)	0.140 (2)
O4	0.7949 (6)	0.6315 (4)	0.3673 (4)	0.160 (2)
O5	0.6168 (3)	0.05094 (19)	0.7505 (2)	0.0617 (7)
H5	0.679 (3)	0.016 (3)	0.758 (3)	0.089 (17)*
N1	0.7459 (5)	0.5650 (4)	0.3876 (4)	0.0993 (15)
C1	0.8227 (4)	0.1658 (3)	0.6847 (3)	0.0530 (9)
C2	0.8560 (5)	0.0862 (3)	0.6479 (3)	0.0705 (12)
H2	0.7951	0.0485	0.6236	0.085*
C3	0.9784 (7)	0.0619 (5)	0.6469 (4)	0.103 (2)
H3	0.9998	0.0074	0.6231	0.124*
C4	1.0676 (6)	0.1176 (7)	0.6805 (5)	0.118 (3)
H4	1.1502	0.1008	0.6801	0.141*
C5	1.0378 (5)	0.1978 (5)	0.7148 (5)	0.108 (2)
H5A	1.1001	0.2360	0.7368	0.130*
C6	0.9150 (4)	0.2230 (3)	0.7172 (3)	0.0756 (14)
H6	0.8946	0.2780	0.7405	0.091*
C7	0.5464 (4)	0.2443 (3)	0.7950 (2)	0.0512 (9)
C8	0.5951 (5)	0.2284 (4)	0.8764 (3)	0.0766 (13)
H8	0.6674	0.1951	0.8851	0.092*
C9	0.5383 (7)	0.2609 (5)	0.9442 (4)	0.0999 (19)
H9	0.5728	0.2496	0.9986	0.120*
C10	0.4323 (7)	0.3094 (4)	0.9338 (4)	0.101 (2)
H10	0.3944	0.3312	0.9806	0.121*
C11	0.3822 (6)	0.3257 (4)	0.8546 (5)	0.1000 (19)
H11	0.3093	0.3585	0.8471	0.120*
C12	0.4384 (5)	0.2940 (3)	0.7847 (4)	0.0764 (14)
H12	0.4035	0.3061	0.7306	0.092*
C13	0.5186 (3)	0.1510 (2)	0.5826 (2)	0.0473 (8)
C14	0.3968 (4)	0.1301 (3)	0.5878 (3)	0.0704 (12)
H14	0.3631	0.1296	0.6402	0.085*
C15	0.3226 (5)	0.1094 (4)	0.5146 (4)	0.0900 (17)
H15	0.2396	0.0954	0.5187	0.108*
C16	0.3702 (6)	0.1096 (3)	0.4381 (4)	0.0908 (18)
H16	0.3198	0.0972	0.3895	0.109*
C17	0.4918 (7)	0.1280 (4)	0.4322 (3)	0.0914 (17)
H17	0.5257	0.1258	0.3799	0.110*
C18	0.5658 (5)	0.1501 (3)	0.5044 (3)	0.0701 (12)
H18	0.6486	0.1644	0.4997	0.084*
C19	0.6831 (4)	0.3978 (3)	0.6536 (3)	0.0520 (9)
C20	0.6661 (4)	0.4765 (2)	0.5946 (2)	0.0493 (9)
C21	0.5921 (4)	0.5464 (3)	0.6191 (3)	0.0634 (11)
H21	0.5564	0.5429	0.6708	0.076*
C22	0.5704 (5)	0.6205 (3)	0.5691 (4)	0.0773 (15)
H22	0.5198	0.6666	0.5861	0.093*
C23	0.6240 (5)	0.6255 (3)	0.4942 (4)	0.0747 (14)
H23	0.6111	0.6757	0.4597	0.090*
C24	0.6958 (4)	0.5577 (3)	0.4699 (3)	0.0660 (11)
C25	0.7200 (4)	0.4793 (3)	0.5179 (3)	0.0589 (10)
C26	0.8001 (6)	0.4023 (4)	0.4908 (4)	0.0979 (18)
H26	0.8447	0.3771	0.5397	0.147*
H26B	0.8576	0.4242	0.4522	0.147*
H26C	0.7486	0.3569	0.4634	0.147*
C27	0.5104 (5)	0.0158 (4)	0.7849 (4)	0.0936 (18)
H27A	0.5287	0.0021	0.8437	0.140*
H27B	0.4849	−0.0380	0.7550	0.140*
H27C	0.4450	0.0594	0.7794	0.140*

	U11	U22	U33	U12	U13	U23
Sn1	0.04851 (16)	0.03856 (15)	0.04577 (16)	0.00015 (10)	−0.00464 (10)	0.00265 (10)
O1	0.0819 (19)	0.0289 (12)	0.0569 (16)	−0.0078 (12)	−0.0114 (14)	0.0025 (11)
O2	0.087 (2)	0.0475 (15)	0.0527 (16)	−0.0111 (14)	−0.0160 (15)	0.0024 (13)
O3	0.152 (5)	0.195 (6)	0.075 (3)	−0.012 (4)	0.021 (3)	−0.002 (4)
O4	0.187 (5)	0.158 (5)	0.139 (5)	−0.054 (4)	0.028 (4)	0.063 (4)
O5	0.0636 (18)	0.0493 (15)	0.073 (2)	0.0051 (13)	0.0088 (15)	0.0157 (14)
N1	0.099 (3)	0.111 (4)	0.087 (4)	−0.007 (3)	0.003 (3)	0.037 (3)
C1	0.050 (2)	0.054 (2)	0.055 (2)	0.0003 (17)	0.0007 (17)	0.0189 (19)
C2	0.078 (3)	0.069 (3)	0.066 (3)	0.012 (2)	0.018 (2)	0.012 (2)
C3	0.098 (5)	0.114 (5)	0.103 (5)	0.041 (4)	0.040 (4)	0.027 (4)
C4	0.061 (4)	0.165 (8)	0.130 (6)	0.031 (4)	0.031 (4)	0.067 (6)
C5	0.054 (3)	0.130 (6)	0.140 (6)	−0.019 (3)	−0.005 (3)	0.047 (5)
C6	0.063 (3)	0.069 (3)	0.093 (4)	−0.010 (2)	−0.011 (3)	0.024 (3)
C7	0.056 (2)	0.045 (2)	0.052 (2)	−0.0054 (16)	0.0022 (17)	−0.0023 (17)
C8	0.075 (3)	0.100 (4)	0.053 (3)	−0.004 (3)	−0.007 (2)	−0.002 (3)
C9	0.108 (5)	0.135 (6)	0.056 (3)	−0.030 (4)	0.007 (3)	−0.015 (3)
C10	0.115 (5)	0.104 (5)	0.090 (5)	−0.041 (4)	0.048 (4)	−0.040 (4)
C11	0.085 (4)	0.091 (4)	0.128 (6)	0.008 (3)	0.033 (4)	−0.020 (4)
C12	0.078 (3)	0.077 (3)	0.074 (3)	0.015 (2)	0.006 (3)	−0.005 (2)
C13	0.058 (2)	0.0339 (17)	0.049 (2)	0.0034 (15)	−0.0081 (17)	−0.0018 (15)
C14	0.067 (3)	0.077 (3)	0.066 (3)	−0.015 (2)	−0.010 (2)	−0.003 (2)
C15	0.077 (3)	0.094 (4)	0.095 (4)	−0.026 (3)	−0.024 (3)	−0.001 (3)
C16	0.127 (5)	0.061 (3)	0.077 (4)	−0.014 (3)	−0.044 (4)	−0.006 (3)
C17	0.124 (5)	0.096 (4)	0.052 (3)	0.005 (4)	−0.011 (3)	−0.015 (3)
C18	0.076 (3)	0.076 (3)	0.058 (3)	0.008 (2)	−0.003 (2)	−0.013 (2)
C19	0.059 (2)	0.045 (2)	0.052 (2)	0.0048 (17)	−0.0002 (19)	−0.0010 (17)
C20	0.061 (2)	0.0312 (16)	0.054 (2)	−0.0017 (15)	−0.0105 (18)	−0.0013 (15)
C21	0.072 (3)	0.042 (2)	0.074 (3)	0.0043 (18)	−0.010 (2)	−0.0046 (19)
C22	0.085 (3)	0.042 (2)	0.101 (4)	0.015 (2)	−0.020 (3)	0.002 (2)
C23	0.078 (3)	0.044 (2)	0.097 (4)	0.001 (2)	−0.031 (3)	0.014 (2)
C24	0.071 (3)	0.067 (3)	0.059 (3)	−0.008 (2)	−0.007 (2)	0.015 (2)
C25	0.069 (3)	0.044 (2)	0.062 (3)	0.0004 (18)	0.001 (2)	0.0051 (18)
C26	0.122 (5)	0.088 (4)	0.088 (4)	0.030 (3)	0.039 (4)	0.010 (3)
C27	0.095 (4)	0.065 (3)	0.124 (5)	0.001 (3)	0.034 (4)	0.022 (3)

Sn1—C1	2.118 (4)	C11—C12	1.383 (8)
Sn1—C7	2.110 (4)	C11—H11	0.9300
Sn1—C13	2.121 (4)	C12—H12	0.9300
Sn1—O1	2.146 (2)	C13—C18	1.371 (6)
Sn1—O5	2.410 (3)	C13—C14	1.364 (6)
O1—C19	1.275 (5)	C14—C15	1.397 (7)
O2—C19	1.218 (4)	C14—H14	0.9300
O3—N1	1.225 (7)	C15—C16	1.349 (8)
O4—N1	1.179 (6)	C15—H15	0.9300
O5—C27	1.410 (6)	C16—C17	1.356 (9)
O5—H5	0.850 (10)	C16—H16	0.9300
N1—C24	1.450 (7)	C17—C18	1.389 (7)
C1—C6	1.384 (6)	C17—H17	0.9300
C1—C2	1.378 (6)	C18—H18	0.9300
C2—C3	1.376 (8)	C19—C20	1.500 (5)
C2—H2	0.9300	C20—C21	1.385 (5)
C3—C4	1.354 (10)	C20—C25	1.384 (6)
C3—H3	0.9300	C21—C22	1.367 (6)
C4—C5	1.360 (10)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.358 (8)
C5—C6	1.386 (8)	C22—H22	0.9300
C5—H5A	0.9300	C23—C24	1.346 (7)
C6—H6	0.9300	C23—H23	0.9300
C7—C8	1.378 (6)	C24—C25	1.407 (6)
C7—C12	1.383 (6)	C25—C26	1.517 (6)
C8—C9	1.363 (8)	C26—H26	0.9600
C8—H8	0.9300	C26—H26B	0.9600
C9—C10	1.357 (9)	C26—H26C	0.9600
C9—H9	0.9300	C27—H27A	0.9600
C10—C11	1.351 (10)	C27—H27B	0.9600
C10—H10	0.9300	C27—H27C	0.9600
C7—Sn1—C1	125.41 (16)	C11—C12—H12	119.8
C7—Sn1—C13	118.16 (15)	C18—C13—C14	118.4 (4)
C1—Sn1—C13	114.98 (16)	C18—C13—Sn1	118.6 (3)
C7—Sn1—O1	96.93 (13)	C14—C13—Sn1	122.7 (3)
C1—Sn1—O1	97.32 (13)	C13—C14—C15	120.2 (5)
C13—Sn1—O1	87.06 (12)	C13—C14—H14	119.9
C7—Sn1—O5	85.35 (13)	C15—C14—H14	119.9
C1—Sn1—O5	84.49 (13)	C16—C15—C14	120.6 (5)
C13—Sn1—O5	88.38 (12)	C16—C15—H15	119.7
O1—Sn1—O5	175.43 (10)	C14—C15—H15	119.7
C19—O1—Sn1	126.7 (3)	C17—C16—C15	119.7 (5)
C27—O5—Sn1	125.3 (3)	C17—C16—H16	120.1
C27—O5—H5	112 (4)	C15—C16—H16	120.1
Sn1—O5—H5	122 (4)	C16—C17—C18	120.0 (6)
O4—N1—O3	119.9 (7)	C16—C17—H17	120.0
O4—N1—C24	120.7 (7)	C18—C17—H17	120.0
O3—N1—C24	119.2 (5)	C13—C18—C17	120.9 (5)
C6—C1—C2	118.8 (4)	C13—C18—H18	119.5
C6—C1—Sn1	122.1 (4)	C17—C18—H18	119.5
C2—C1—Sn1	119.1 (3)	O2—C19—O1	126.0 (4)
C1—C2—C3	120.8 (6)	O2—C19—C20	119.9 (3)
C1—C2—H2	119.6	O1—C19—C20	114.1 (3)
C3—C2—H2	119.6	C21—C20—C25	120.7 (4)
C4—C3—C2	119.8 (6)	C21—C20—C19	117.4 (4)
C4—C3—H3	120.1	C25—C20—C19	121.8 (3)
C2—C3—H3	120.1	C22—C21—C20	121.5 (5)
C5—C4—C3	120.7 (6)	C22—C21—H21	119.2
C5—C4—H4	119.6	C20—C21—H21	119.2
C3—C4—H4	119.6	C21—C22—C23	118.8 (5)
C4—C5—C6	120.3 (6)	C21—C22—H22	120.6
C4—C5—H5A	119.9	C23—C22—H22	120.6
C6—C5—H5A	119.9	C24—C23—C22	120.0 (4)
C1—C6—C5	119.6 (6)	C24—C23—H23	120.0
C1—C6—H6	120.2	C22—C23—H23	120.0
C5—C6—H6	120.2	C23—C24—C25	123.8 (5)
C8—C7—C12	117.8 (4)	C23—C24—N1	117.5 (5)
C8—C7—Sn1	122.1 (3)	C25—C24—N1	118.6 (5)
C12—C7—Sn1	120.0 (3)	C20—C25—C24	115.1 (4)
C9—C8—C7	120.7 (5)	C20—C25—C26	120.7 (4)
C9—C8—H8	119.6	C24—C25—C26	124.2 (4)
C7—C8—H8	119.6	C25—C26—H26	109.5
C8—C9—C10	121.2 (6)	C25—C26—H26B	109.5
C8—C9—H9	119.4	H26—C26—H26B	109.5
C10—C9—H9	119.4	C25—C26—H26C	109.5
C11—C10—C9	119.3 (6)	H26—C26—H26C	109.5
C11—C10—H10	120.3	H26B—C26—H26C	109.5
C9—C10—H10	120.3	O5—C27—H27A	109.5
C10—C11—C12	120.6 (6)	O5—C27—H27B	109.5
C10—C11—H11	119.7	H27A—C27—H27B	109.5
C12—C11—H11	119.7	O5—C27—H27C	109.5
C7—C12—C11	120.3 (6)	H27A—C27—H27C	109.5
C7—C12—H12	119.8	H27B—C27—H27C	109.5
C7—Sn1—O1—C19	53.5 (3)	C1—Sn1—C13—C18	−35.2 (4)
C1—Sn1—O1—C19	−73.7 (3)	O1—Sn1—C13—C18	61.5 (3)
C13—Sn1—O1—C19	171.5 (3)	O5—Sn1—C13—C18	−118.4 (3)
C7—Sn1—O5—C27	46.3 (4)	C7—Sn1—C13—C14	−15.7 (4)
C1—Sn1—O5—C27	172.6 (4)	C1—Sn1—C13—C14	151.3 (3)
C13—Sn1—O5—C27	−72.1 (4)	O1—Sn1—C13—C14	−112.0 (3)
C7—Sn1—C1—C6	−48.3 (4)	O5—Sn1—C13—C14	68.2 (3)
C13—Sn1—C1—C6	145.8 (3)	C18—C13—C14—C15	−0.7 (7)
O1—Sn1—C1—C6	55.7 (4)	Sn1—C13—C14—C15	172.7 (4)
O5—Sn1—C1—C6	−128.6 (4)	C13—C14—C15—C16	0.1 (8)
C7—Sn1—C1—C2	132.7 (3)	C14—C15—C16—C17	1.6 (9)
C13—Sn1—C1—C2	−33.2 (4)	C15—C16—C17—C18	−2.6 (9)
O1—Sn1—C1—C2	−123.4 (3)	C14—C13—C18—C17	−0.3 (7)
O5—Sn1—C1—C2	52.4 (3)	Sn1—C13—C18—C17	−174.1 (4)
C6—C1—C2—C3	2.9 (7)	C16—C17—C18—C13	2.0 (8)
Sn1—C1—C2—C3	−178.1 (4)	Sn1—O1—C19—O2	3.2 (6)
C1—C2—C3—C4	−1.5 (9)	Sn1—O1—C19—C20	−176.5 (3)
C2—C3—C4—C5	−0.5 (10)	O2—C19—C20—C21	−64.5 (5)
C3—C4—C5—C6	1.2 (11)	O1—C19—C20—C21	115.2 (4)
C2—C1—C6—C5	−2.2 (7)	O2—C19—C20—C25	116.6 (5)
Sn1—C1—C6—C5	178.8 (4)	O1—C19—C20—C25	−63.7 (5)
C4—C5—C6—C1	0.2 (9)	C25—C20—C21—C22	−0.5 (6)
C1—Sn1—C7—C8	−23.2 (4)	C19—C20—C21—C22	−179.4 (4)
C13—Sn1—C7—C8	142.3 (4)	C20—C21—C22—C23	−0.7 (7)
O1—Sn1—C7—C8	−127.3 (4)	C21—C22—C23—C24	0.8 (7)
O5—Sn1—C7—C8	56.6 (4)	C22—C23—C24—C25	0.2 (7)
C1—Sn1—C7—C12	155.6 (3)	C22—C23—C24—N1	177.2 (5)
C13—Sn1—C7—C12	−38.8 (4)	O4—N1—C24—C23	48.4 (8)
O1—Sn1—C7—C12	51.5 (4)	O3—N1—C24—C23	−126.4 (6)
O5—Sn1—C7—C12	−124.5 (4)	O4—N1—C24—C25	−134.5 (6)
C12—C7—C8—C9	−0.1 (7)	O3—N1—C24—C25	50.7 (8)
Sn1—C7—C8—C9	178.8 (4)	C21—C20—C25—C24	1.4 (6)
C7—C8—C9—C10	0.3 (9)	C19—C20—C25—C24	−179.7 (4)
C8—C9—C10—C11	0.0 (10)	C21—C20—C25—C26	−179.5 (5)
C9—C10—C11—C12	−0.4 (10)	C19—C20—C25—C26	−0.6 (6)
C8—C7—C12—C11	−0.3 (7)	C23—C24—C25—C20	−1.3 (7)
Sn1—C7—C12—C11	−179.2 (4)	N1—C24—C25—C20	−178.3 (4)
C10—C11—C12—C7	0.6 (9)	C23—C24—C25—C26	179.6 (5)
C7—Sn1—C13—C18	157.8 (3)	N1—C24—C25—C26	2.6 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2i	0.85 (1)	1.87 (2)	2.676 (4)	158 (5)

Table 1

Selected bond lengths (Å)

Sn1—C1	2.118 (4)
Sn1—C7	2.110 (4)
Sn1—C13	2.121 (4)
Sn1—O1	2.146 (2)
Sn1—O5	2.410 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O2i	0.85 (1)	1.87 (2)	2.676 (4)	158 (5)

Symmetry code: (i) .