catena-Poly[[tribenzyl­tin(IV)]-μ-4-formyl-2-meth­oxy-6-nitro­phenolato-κ2O1:O4]

Keng, T.C.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536811016436

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page m710

doi:10.1107/S1600536811016436

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catena-Poly[[tribenzyltin(IV)]-μ-4-formyl-2-methoxy-6-nitrophenolato-κ²O¹:O⁴]

Thy Chun Keng,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 25 April 2011; accepted 30 April 2011; online 7 May 2011)

The formylmethoxynitrophenoxide ions in the polymeric title compound, [Sn(C₇H₇)₃(C₈H₆NO₅)]_n, link adjacent triorganotin(IV) cations into linear chains lying close to (101) [Sn—O = 2.1227 (12) Å and Sn← O = 2.4936 (13) Å]. The Sn^IV atom is displaced out of the C₃Sn girdle of the trans-C₃SnO₂ trigonal-bipyramidal polyhedron in the direction of the covalently-bonded O atom [Sn—O—C = 137.63 (11)°] by 0.247 (1) Å; the geometry is distorted towards an octahedron by a remote O atom of the methoxy subsituent [Sn⋯O = 3.019 (1) Å]

Related literature

For a related structure, see: James et al. (1998 ). For a description of triorganotin phenoxides, see: Poller (1970 ).

Experimental

Crystal data

[Sn(C₇H₇)₃(C₈H₆NO₅)]
M_r = 588.21
Monoclinic, P 2₁ /n
a = 12.1241 (1) Å
b = 16.5829 (2) Å
c = 13.3893 (2) Å
β = 106.3701 (6)°
V = 2582.83 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 100 K
0.25 × 0.25 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.783, T_max = 0.904
25760 measured reflections
6372 independent reflections
5545 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.063
S = 1.01
6372 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 1.02 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016436/jh2283sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016436/jh2283Isup2.hkl

checkCIF report

Comment top

Triorganotin alkoxides are compounds, unlike triorganotin phenoxides, which are generally not stable in air, as stated in a textbook on organotin chemistry (Poller, 1970). As such, there are few reports on phenoxides. Vanillin and its derivatives possess a hydroxy group that can be deprotonated; the 5-nitrovallinate anion in polymeric [Sn(C₇H₇)₃(C₈H₇NO₅)]_n (Scheme I) links adjacent triorganotin(IV) cations to form a linear chain running along the a–c diagonal of the monoclinic unit cell (Fig. 1). The dative Sn–O bond is significantly longer than the covalent Sn–O bond [Sn–O 2.123 (1), Sn←O 2.494 (1) Å], so that the Sn^IV atom is displaced out of the C₃Sn girdle of the trans-C₃SnO₂ trigonal bipyramidal polyhedron in the direction of the covalently-bonded O atom [Sn–O–C 137.6 (1) Å] by 0.247 (1) Å. The geometry is distorted towards an octahedron by the O atom of the methoxy subsituent [Sn···O 3.019 (1) Å]. There are few examples of triorganotin systems having Sn←O_{aromatic aldehdye} bond; one example is triphenyltin salicylaldehydate, which features a long Sn←O bond (James et al., 1998).

Related literature top

For a related structure, see: James et al. (1998). For a description of triorganotin phenoxides, see: Poller (1970).

Experimental top

Tribenzyltin hydroxide was prepared by the base hydrolysis of tribenzyl)tin chloride with 10% sodium hydroxide solution. The compound (0.41 g, 1 mmol) hydroxide and 4-hydroxy-3-methoxy-5-nitrobenzaldehyde (5-nitrovanillin) (0.2 g, 1 mmol) were dissolved in ethanol (100 ml) and the mixture was heated for an hour. The solution was filtered and the solvent allowed to evaporate for a few days.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of a portion of the chain structure of Sn(C₇H₇)₃(C₈H₆NO₅) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

catena-Poly[[tribenzyltin(IV)]-µ-4-formyl-2-methoxy-6- nitrophenolato-κ²O¹:O⁴] top

Crystal data top

[Sn(C₇H₇)₃(C₈H₆NO₅)]	F(000) = 1192
M_r = 588.21	D_x = 1.513 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9964 reflections
a = 12.1241 (1) Å	θ = 2.4–28.2°
b = 16.5829 (2) Å	µ = 1.03 mm⁻¹
c = 13.3893 (2) Å	T = 100 K
β = 106.3701 (6)°	Block, colorless
V = 2582.83 (5) Å³	0.25 × 0.25 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	6372 independent reflections
Radiation source: fine-focus sealed tube	5545 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.783, T_max = 0.904	k = −22→21
25760 measured reflections	l = −17→17

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0349P)² + 0.888P] where P = (F_o² + 2F_c²)/3
6372 reflections	(Δ/σ)_max = 0.001
325 parameters	Δρ_max = 1.02 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Sn(C₇H₇)₃(C₈H₆NO₅)]	V = 2582.83 (5) Å³
M_r = 588.21	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.1241 (1) Å	µ = 1.03 mm⁻¹
b = 16.5829 (2) Å	T = 100 K
c = 13.3893 (2) Å	0.25 × 0.25 × 0.10 mm
β = 106.3701 (6)°

Data collection top

Bruker SMART APEX diffractometer	6372 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5545 reflections with I > 2σ(I)
T_min = 0.783, T_max = 0.904	R_int = 0.028
25760 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.01	Δρ_max = 1.02 e Å⁻³
6372 reflections	Δρ_min = −0.25 e Å⁻³
325 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.368458 (10)	0.189545 (7)	0.722727 (9)	0.01643 (5)
O1	0.27411 (11)	0.13103 (7)	0.81338 (10)	0.0204 (3)
O2	0.28459 (11)	0.27891 (8)	0.88378 (11)	0.0218 (3)
O3	−0.01389 (12)	0.27479 (8)	1.10347 (11)	0.0262 (3)
O4	0.04948 (13)	−0.03179 (8)	0.87527 (11)	0.0296 (3)
O5	0.15153 (15)	−0.00208 (10)	0.77303 (13)	0.0426 (4)
N1	0.10833 (14)	0.01628 (9)	0.84212 (12)	0.0218 (3)
C1	0.38886 (16)	0.07215 (11)	0.66076 (14)	0.0209 (4)
H1A	0.4702	0.0645	0.6619	0.025*
H1B	0.3691	0.0300	0.7052	0.025*
C2	0.31382 (16)	0.06304 (11)	0.55183 (14)	0.0215 (4)
C3	0.3568 (2)	0.07057 (14)	0.46631 (17)	0.0343 (5)
H3	0.4368	0.0790	0.4768	0.041*
C4	0.2842 (2)	0.06586 (17)	0.36588 (18)	0.0449 (6)
H4	0.3150	0.0714	0.3084	0.054*
C5	0.1676 (2)	0.05316 (15)	0.34835 (18)	0.0411 (6)
H5	0.1183	0.0501	0.2793	0.049*
C6	0.12380 (18)	0.04503 (12)	0.43205 (18)	0.0315 (5)
H6	0.0438	0.0361	0.4208	0.038*
C7	0.19544 (17)	0.04974 (11)	0.53232 (16)	0.0245 (4)
H7	0.1639	0.0439	0.5893	0.029*
C8	0.23785 (17)	0.26471 (12)	0.62210 (16)	0.0250 (4)
H8A	0.2716	0.3188	0.6193	0.030*
H8B	0.2191	0.2419	0.5510	0.030*
C9	0.12731 (16)	0.27558 (12)	0.65014 (14)	0.0215 (4)
C10	0.05093 (18)	0.21194 (12)	0.64538 (16)	0.0263 (4)
H10	0.0688	0.1603	0.6236	0.032*
C11	−0.05074 (17)	0.22273 (14)	0.67194 (17)	0.0305 (4)
H11	−0.1013	0.1785	0.6689	0.037*
C12	−0.07859 (19)	0.29776 (14)	0.70286 (18)	0.0350 (5)
H12	−0.1483	0.3053	0.7209	0.042*
C13	−0.00443 (18)	0.36165 (13)	0.70734 (18)	0.0325 (5)
H13	−0.0233	0.4133	0.7285	0.039*
C14	0.09776 (17)	0.35095 (12)	0.68101 (15)	0.0259 (4)
H14	0.1479	0.3955	0.6841	0.031*
C15	0.51642 (16)	0.22724 (12)	0.84500 (15)	0.0242 (4)
H15A	0.5502	0.2766	0.8240	0.029*
H15B	0.4943	0.2391	0.9092	0.029*
C16	0.60161 (16)	0.15935 (12)	0.86363 (14)	0.0221 (4)
C17	0.59103 (17)	0.09386 (12)	0.92531 (15)	0.0264 (4)
H17	0.5317	0.0937	0.9589	0.032*
C18	0.66561 (18)	0.02880 (13)	0.93860 (16)	0.0305 (4)
H18	0.6574	−0.0152	0.9814	0.037*
C19	0.75189 (19)	0.02786 (15)	0.88964 (17)	0.0346 (5)
H19	0.8027	−0.0169	0.8981	0.042*
C20	0.76353 (18)	0.09220 (15)	0.82865 (17)	0.0368 (5)
H20	0.8227	0.0917	0.7949	0.044*
C21	0.69000 (17)	0.15770 (14)	0.81585 (17)	0.0303 (4)
H21	0.6999	0.2019	0.7741	0.036*
C22	0.20411 (15)	0.15092 (11)	0.86575 (13)	0.0170 (3)
C23	0.20697 (15)	0.23057 (11)	0.91021 (14)	0.0186 (3)
C24	0.13811 (15)	0.25138 (11)	0.97130 (14)	0.0198 (4)
H24	0.1428	0.3039	1.0007	0.024*
C25	0.05980 (16)	0.19419 (11)	0.99044 (14)	0.0204 (4)
C26	0.05257 (16)	0.11815 (11)	0.94786 (14)	0.0202 (4)
H26	−0.0005	0.0802	0.9607	0.024*
C27	0.12282 (15)	0.09688 (10)	0.88604 (14)	0.0180 (3)
C28	−0.01506 (17)	0.21211 (12)	1.05483 (16)	0.0246 (4)
H28	−0.0694	0.1721	1.0597	0.030*
C29	0.28924 (18)	0.36164 (11)	0.91567 (16)	0.0258 (4)
H29A	0.3482	0.3900	0.8920	0.039*
H29B	0.3083	0.3645	0.9917	0.039*
H29C	0.2143	0.3871	0.8851	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01783 (7)	0.01555 (7)	0.01806 (7)	0.00019 (4)	0.00854 (5)	0.00098 (4)
O1	0.0242 (7)	0.0177 (6)	0.0241 (7)	0.0014 (5)	0.0149 (5)	0.0016 (5)
O2	0.0257 (7)	0.0157 (6)	0.0285 (7)	−0.0025 (5)	0.0148 (6)	−0.0009 (5)
O3	0.0320 (8)	0.0237 (7)	0.0289 (7)	0.0005 (6)	0.0183 (6)	−0.0035 (6)
O4	0.0402 (8)	0.0228 (7)	0.0312 (8)	−0.0108 (6)	0.0186 (6)	−0.0012 (6)
O5	0.0593 (11)	0.0319 (9)	0.0528 (11)	−0.0168 (7)	0.0424 (9)	−0.0188 (7)
N1	0.0243 (8)	0.0199 (8)	0.0224 (8)	−0.0030 (6)	0.0088 (6)	−0.0005 (6)
C1	0.0230 (9)	0.0198 (9)	0.0219 (9)	0.0019 (7)	0.0098 (7)	−0.0002 (7)
C2	0.0256 (9)	0.0164 (8)	0.0234 (9)	0.0004 (7)	0.0087 (7)	−0.0003 (7)
C3	0.0347 (12)	0.0426 (13)	0.0299 (11)	−0.0121 (10)	0.0160 (9)	−0.0065 (10)
C4	0.0574 (16)	0.0559 (16)	0.0255 (11)	−0.0199 (13)	0.0183 (11)	−0.0060 (11)
C5	0.0479 (14)	0.0404 (13)	0.0281 (11)	−0.0067 (11)	−0.0004 (10)	−0.0039 (10)
C6	0.0280 (11)	0.0240 (10)	0.0402 (12)	0.0007 (8)	0.0056 (9)	−0.0034 (9)
C7	0.0276 (10)	0.0176 (9)	0.0309 (10)	0.0012 (7)	0.0125 (8)	−0.0024 (8)
C8	0.0273 (10)	0.0257 (10)	0.0260 (10)	0.0064 (8)	0.0138 (8)	0.0070 (8)
C9	0.0225 (9)	0.0246 (9)	0.0184 (9)	0.0054 (7)	0.0076 (7)	0.0040 (7)
C10	0.0304 (11)	0.0248 (10)	0.0231 (10)	0.0025 (8)	0.0066 (8)	−0.0007 (8)
C11	0.0239 (10)	0.0359 (11)	0.0307 (11)	−0.0049 (9)	0.0060 (8)	−0.0004 (9)
C12	0.0213 (10)	0.0457 (13)	0.0403 (13)	0.0029 (9)	0.0125 (9)	−0.0038 (10)
C13	0.0292 (11)	0.0290 (11)	0.0409 (12)	0.0078 (9)	0.0125 (9)	−0.0032 (9)
C14	0.0258 (10)	0.0240 (10)	0.0284 (10)	0.0040 (8)	0.0086 (8)	0.0021 (8)
C15	0.0236 (10)	0.0229 (9)	0.0271 (10)	−0.0038 (8)	0.0089 (8)	−0.0062 (8)
C16	0.0178 (9)	0.0262 (9)	0.0211 (9)	−0.0029 (7)	0.0036 (7)	−0.0053 (8)
C17	0.0224 (10)	0.0328 (11)	0.0234 (10)	−0.0047 (8)	0.0059 (7)	−0.0014 (8)
C18	0.0272 (10)	0.0323 (11)	0.0279 (10)	−0.0001 (8)	0.0009 (8)	0.0028 (9)
C19	0.0285 (11)	0.0413 (13)	0.0297 (11)	0.0103 (9)	0.0013 (9)	−0.0015 (10)
C20	0.0227 (10)	0.0572 (15)	0.0321 (11)	0.0088 (10)	0.0106 (9)	0.0027 (11)
C21	0.0227 (10)	0.0398 (12)	0.0299 (11)	−0.0001 (9)	0.0096 (8)	0.0061 (9)
C22	0.0193 (9)	0.0181 (9)	0.0143 (8)	0.0024 (7)	0.0056 (6)	0.0027 (7)
C23	0.0197 (9)	0.0172 (8)	0.0197 (9)	0.0003 (7)	0.0071 (7)	0.0035 (7)
C24	0.0244 (9)	0.0172 (8)	0.0191 (9)	0.0011 (7)	0.0084 (7)	0.0003 (7)
C25	0.0227 (9)	0.0221 (9)	0.0194 (9)	0.0015 (7)	0.0110 (7)	0.0015 (7)
C26	0.0209 (9)	0.0206 (9)	0.0220 (9)	−0.0010 (7)	0.0106 (7)	0.0025 (7)
C27	0.0213 (9)	0.0155 (8)	0.0182 (8)	0.0000 (7)	0.0072 (7)	−0.0004 (7)
C28	0.0274 (10)	0.0223 (9)	0.0291 (10)	0.0002 (8)	0.0159 (8)	0.0017 (8)
C29	0.0318 (11)	0.0165 (9)	0.0313 (10)	−0.0043 (8)	0.0125 (8)	−0.0019 (8)

Geometric parameters (Å, º) top

Sn1—O1	2.1227 (12)	C11—C12	1.383 (3)
Sn1—C15	2.1526 (19)	C11—H11	0.9500
Sn1—C1	2.1576 (18)	C12—C13	1.380 (3)
Sn1—C8	2.1619 (19)	C12—H12	0.9500
Sn1—O3ⁱ	2.4936 (13)	C13—C14	1.392 (3)
O1—C22	1.287 (2)	C13—H13	0.9500
O2—C23	1.357 (2)	C14—H14	0.9500
O2—C29	1.433 (2)	C15—C16	1.500 (3)
O3—C28	1.225 (2)	C15—H15A	0.9900
O3—Sn1ⁱⁱ	2.4936 (13)	C15—H15B	0.9900
O4—N1	1.233 (2)	C16—C17	1.392 (3)
O5—N1	1.223 (2)	C16—C21	1.395 (3)
N1—C27	1.451 (2)	C17—C18	1.387 (3)
C1—C2	1.493 (3)	C17—H17	0.9500
C1—H1A	0.9900	C18—C19	1.382 (3)
C1—H1B	0.9900	C18—H18	0.9500
C2—C3	1.391 (3)	C19—C20	1.375 (3)
C2—C7	1.402 (3)	C19—H19	0.9500
C3—C4	1.386 (3)	C20—C21	1.385 (3)
C3—H3	0.9500	C20—H20	0.9500
C4—C5	1.382 (4)	C21—H21	0.9500
C4—H4	0.9500	C22—C27	1.414 (2)
C5—C6	1.375 (3)	C22—C23	1.445 (3)
C5—H5	0.9500	C23—C24	1.367 (2)
C6—C7	1.380 (3)	C24—C25	1.416 (2)
C6—H6	0.9500	C24—H24	0.9500
C7—H7	0.9500	C25—C26	1.377 (3)
C8—C9	1.501 (3)	C25—C28	1.448 (3)
C8—H8A	0.9900	C26—C27	1.390 (2)
C8—H8B	0.9900	C26—H26	0.9500
C9—C10	1.394 (3)	C28—H28	0.9500
C9—C14	1.395 (3)	C29—H29A	0.9800
C10—C11	1.387 (3)	C29—H29B	0.9800
C10—H10	0.9500	C29—H29C	0.9800

O1—Sn1—C15	99.54 (6)	C12—C13—C14	120.5 (2)
O1—Sn1—C1	86.91 (6)	C12—C13—H13	119.8
C15—Sn1—C1	113.15 (7)	C14—C13—H13	119.8
O1—Sn1—C8	101.64 (6)	C13—C14—C9	120.71 (19)
C15—Sn1—C8	127.85 (8)	C13—C14—H14	119.6
C1—Sn1—C8	115.07 (8)	C9—C14—H14	119.6
O1—Sn1—O3ⁱ	166.47 (5)	C16—C15—Sn1	107.19 (12)
C15—Sn1—O3ⁱ	85.05 (6)	C16—C15—H15A	110.3
C1—Sn1—O3ⁱ	79.60 (6)	Sn1—C15—H15A	110.3
C8—Sn1—O3ⁱ	85.12 (6)	C16—C15—H15B	110.3
C22—O1—Sn1	137.63 (11)	Sn1—C15—H15B	110.3
C23—O2—C29	117.37 (14)	H15A—C15—H15B	108.5
C28—O3—Sn1ⁱⁱ	128.23 (13)	C17—C16—C21	117.91 (19)
O5—N1—O4	121.74 (16)	C17—C16—C15	120.65 (17)
O5—N1—C27	120.47 (15)	C21—C16—C15	121.36 (18)
O4—N1—C27	117.77 (15)	C16—C17—C18	121.16 (19)
C2—C1—Sn1	111.26 (12)	C16—C17—H17	119.4
C2—C1—H1A	109.4	C18—C17—H17	119.4
Sn1—C1—H1A	109.4	C19—C18—C17	120.1 (2)
C2—C1—H1B	109.4	C19—C18—H18	120.0
Sn1—C1—H1B	109.4	C17—C18—H18	120.0
H1A—C1—H1B	108.0	C20—C19—C18	119.4 (2)
C3—C2—C7	117.52 (18)	C20—C19—H19	120.3
C3—C2—C1	121.91 (17)	C18—C19—H19	120.3
C7—C2—C1	120.52 (17)	C19—C20—C21	120.8 (2)
C4—C3—C2	120.7 (2)	C19—C20—H20	119.6
C4—C3—H3	119.6	C21—C20—H20	119.6
C2—C3—H3	119.6	C20—C21—C16	120.6 (2)
C5—C4—C3	120.8 (2)	C20—C21—H21	119.7
C5—C4—H4	119.6	C16—C21—H21	119.7
C3—C4—H4	119.6	O1—C22—C27	123.00 (16)
C6—C5—C4	119.2 (2)	O1—C22—C23	121.05 (16)
C6—C5—H5	120.4	C27—C22—C23	115.93 (15)
C4—C5—H5	120.4	O2—C23—C24	126.31 (17)
C5—C6—C7	120.4 (2)	O2—C23—C22	111.73 (15)
C5—C6—H6	119.8	C24—C23—C22	121.95 (16)
C7—C6—H6	119.8	C23—C24—C25	119.54 (17)
C6—C7—C2	121.38 (19)	C23—C24—H24	120.2
C6—C7—H7	119.3	C25—C24—H24	120.2
C2—C7—H7	119.3	C26—C25—C24	120.43 (17)
C9—C8—Sn1	117.52 (13)	C26—C25—C28	117.20 (17)
C9—C8—H8A	107.9	C24—C25—C28	122.37 (17)
Sn1—C8—H8A	107.9	C25—C26—C27	120.06 (17)
C9—C8—H8B	107.9	C25—C26—H26	120.0
Sn1—C8—H8B	107.9	C27—C26—H26	120.0
H8A—C8—H8B	107.2	C26—C27—C22	122.06 (16)
C10—C9—C14	118.00 (18)	C26—C27—N1	116.78 (16)
C10—C9—C8	121.76 (18)	C22—C27—N1	121.16 (15)
C14—C9—C8	120.25 (18)	O3—C28—C25	125.14 (18)
C11—C10—C9	121.16 (19)	O3—C28—H28	117.4
C11—C10—H10	119.4	C25—C28—H28	117.4
C9—C10—H10	119.4	O2—C29—H29A	109.5
C12—C11—C10	120.2 (2)	O2—C29—H29B	109.5
C12—C11—H11	119.9	H29A—C29—H29B	109.5
C10—C11—H11	119.9	O2—C29—H29C	109.5
C13—C12—C11	119.5 (2)	H29A—C29—H29C	109.5
C13—C12—H12	120.2	H29B—C29—H29C	109.5
C11—C12—H12	120.2

C15—Sn1—O1—C22	83.51 (18)	Sn1—C15—C16—C21	95.27 (19)
C1—Sn1—O1—C22	−163.52 (18)	C21—C16—C17—C18	−0.3 (3)
C8—Sn1—O1—C22	−48.54 (18)	C15—C16—C17—C18	176.55 (18)
O3ⁱ—Sn1—O1—C22	−167.57 (18)	C16—C17—C18—C19	−0.5 (3)
O1—Sn1—C1—C2	105.81 (13)	C17—C18—C19—C20	0.6 (3)
C15—Sn1—C1—C2	−155.13 (12)	C18—C19—C20—C21	0.0 (3)
C8—Sn1—C1—C2	4.40 (15)	C19—C20—C21—C16	−0.8 (3)
O3ⁱ—Sn1—C1—C2	−75.15 (13)	C17—C16—C21—C20	0.9 (3)
Sn1—C1—C2—C3	101.24 (19)	C15—C16—C21—C20	−175.92 (19)
Sn1—C1—C2—C7	−76.10 (19)	Sn1—O1—C22—C27	155.51 (14)
C7—C2—C3—C4	0.7 (3)	Sn1—O1—C22—C23	−26.3 (3)
C1—C2—C3—C4	−176.7 (2)	C29—O2—C23—C24	−5.3 (3)
C2—C3—C4—C5	−0.3 (4)	C29—O2—C23—C22	174.93 (15)
C3—C4—C5—C6	−0.1 (4)	O1—C22—C23—O2	3.8 (2)
C4—C5—C6—C7	0.2 (4)	C27—C22—C23—O2	−177.92 (15)
C5—C6—C7—C2	0.2 (3)	O1—C22—C23—C24	−176.01 (16)
C3—C2—C7—C6	−0.6 (3)	C27—C22—C23—C24	2.3 (3)
C1—C2—C7—C6	176.85 (17)	O2—C23—C24—C25	178.99 (17)
O1—Sn1—C8—C9	13.55 (16)	C22—C23—C24—C25	−1.2 (3)
C15—Sn1—C8—C9	−98.44 (16)	C23—C24—C25—C26	−0.1 (3)
C1—Sn1—C8—C9	105.59 (16)	C23—C24—C25—C28	179.63 (18)
O3ⁱ—Sn1—C8—C9	−178.30 (16)	C24—C25—C26—C27	0.3 (3)
Sn1—C8—C9—C10	−67.3 (2)	C28—C25—C26—C27	−179.43 (17)
Sn1—C8—C9—C14	113.34 (18)	C25—C26—C27—C22	0.8 (3)
C14—C9—C10—C11	−0.9 (3)	C25—C26—C27—N1	−178.67 (16)
C8—C9—C10—C11	179.72 (19)	O1—C22—C27—C26	176.18 (17)
C9—C10—C11—C12	0.6 (3)	C23—C22—C27—C26	−2.1 (3)
C10—C11—C12—C13	−0.2 (3)	O1—C22—C27—N1	−4.3 (3)
C11—C12—C13—C14	0.0 (3)	C23—C22—C27—N1	177.42 (15)
C12—C13—C14—C9	−0.3 (3)	O5—N1—C27—C26	167.06 (18)
C10—C9—C14—C13	0.7 (3)	O4—N1—C27—C26	−11.5 (2)
C8—C9—C14—C13	−179.89 (19)	O5—N1—C27—C22	−12.4 (3)
O1—Sn1—C15—C16	88.15 (13)	O4—N1—C27—C22	169.03 (17)
C1—Sn1—C15—C16	−2.56 (15)	Sn1ⁱⁱ—O3—C28—C25	−177.02 (14)
C8—Sn1—C15—C16	−158.91 (12)	C26—C25—C28—O3	175.07 (19)
O3ⁱ—Sn1—C15—C16	−79.02 (13)	C24—C25—C28—O3	−4.7 (3)
Sn1—C15—C16—C17	−81.43 (19)

Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Sn(C₇H₇)₃(C₈H₆NO₅)]
M_r	588.21
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	12.1241 (1), 16.5829 (2), 13.3893 (2)
β (°)	106.3701 (6)
V (Å³)	2582.83 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.25 × 0.25 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.783, 0.904
No. of measured, independent and observed [I > 2σ(I)] reflections	25760, 6372, 5545
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.063, 1.01
No. of reflections	6372
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.02, −0.25

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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