catena-Poly[[triphenyl­tin(IV)]-μ-5-amino-2-nitro­benzoato-κ2O1:O1′]

Win, Y.-F.; Choong, C.-S.; Teoh, S.-G.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536811033332

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages m1276-m1277

doi:10.1107/S1600536811033332

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catena-Poly[[triphenyltin(IV)]-μ-5-amino-2-nitrobenzoato-κ²O¹:O^1′]

Yip-Foo Win,^a Chen-Shang Choong,^a Siang-Guan Teoh,^b Ching Kheng Quah ^c ‡ and Hoong-Kun Fun ^c ^*§

^aDepartment of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Perak Campus, Jalan Universiti, Bandar Barat, 31900 Kampar, Perak, Malaysia, ^bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 12 August 2011; accepted 16 August 2011; online 27 August 2011)

The title compound, [Sn(C₆H₅)₃(C₇H₅N₂O₄)]_n, forms polymeric chains along [010]. The Sn^IV ion is five-coordinated in a distorted trigonal–bipyramidal geometry by two monodentate carboxylate groups and three phenyl rings. The axial sites are occupied by the O atoms of two symmetry-related carboxylate groups [O—Sn—O = 170.88 (3)°]. The benzene ring of the 5-amino-2-nitrobenzoate ligand forms dihedral angles of 82.92 (6), 81.10 (6) and 83.54 (6)° with respect to the three phenyl rings. In the crystal, the chains are linked by intermolecular N—H⋯O and weak C—H⋯O interactions into a three-dimensional network. The crystal structure is further stabilized by weak intermolecular C—H⋯π interactions.

Related literature

For general background to and the coordination environment of triphenyltin(IV) carboxylate complexes, see: Yeap & Teoh (2003 ); Win et al. (2006 , 2008 , 2011a ,b ,c ). For standard bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₇H₅N₂O₄)]
M_r = 531.12
Monoclinic, P 2₁ /c
a = 10.9752 (1) Å
b = 11.8342 (1) Å
c = 17.4160 (2) Å
β = 102.164 (1)°
V = 2211.25 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.19 mm⁻¹
T = 100 K
0.37 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.671, T_max = 0.783
27219 measured reflections
7981 independent reflections
7370 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.018
wR(F²) = 0.046
S = 1.07
7981 reflections
297 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2N1⋯O1ⁱ	0.85 (2)	2.498 (19)	3.0619 (14)	124.3 (15)
C5—H5A⋯O4ⁱⁱ	0.95	2.40	3.3288 (16)	167
C3—H3A⋯Cg2ⁱⁱⁱ	0.95	2.58	3.4430 (14)	152
C21—H21A⋯Cg1^iv	0.95	2.70	3.4669 (12)	138
Symmetry codes: (i) -x+2, -y+1, -z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033332/lh5316sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033332/lh5316Isup2.hkl

checkCIF report

Comment top

Generally, the tin(IV) atom moiety of triphenyltin(IV) carboxylate complexes could existed as four- or five-coordinated depending on the coordination manner of the carboxylate anions and the coordinating solvent (Yeap and Teoh, 2003; Win et al., 2006; 2008; 2011a,b,c). In this study, the title complex is found to be similar to the reported structure of (2-amino-5-nitrobenzoato)triphenyltin(IV) (Win et al., 2006) except that the amino group is substituted at meta-position and the nitro group is substituted at ortho-position to the benzoate group.

The asymmetric unit of the title compound is shown in Fig. 1. The overall structure consists of polymeric one-dimensional chains along [010] (Fig. 2). The Sn1 atom is five-coordinate, with a distorted trigonal-bipyramidal coordination geometry, formed by two monodentate symmetry related carboxylate groups and three phenyl rings. The axial sites are occupied by the O atoms of the two carboxylate groups [O1-Sn1-O2ⁱ = 170.88 (3)°, symmetry code: (i) 2-x,-1/2+y,1/2-z], with the three phenyl rings occupying the equatorial plane. Bond lengths (Allen et al., 1987) and angles are within normal ranges. The benzene ring (C20-C25) of the 5-amino-2-nitrobenzoato ligand makes dihedral angles of 82.92 (6), 81.10 (6) and 83.54 (6)° with respect to the three phenyl rings (C1-C6, C7-C12 and C13-C18).

In the crystal (Fig. 3), the polymeric one-dimensional chains are linked by intermolecular N1–H2N1···O1ⁱⁱⁱ and weak C5–H5A···O4^iv interactions into a three-dimensional network. The crystal structure is further consolidated by C21–H21A···Cg1ⁱⁱ and C3–H3A···Cg2^v (Table 1) interactions, where Cg1 and Cg2 are the centroids of C1-C6 and C7-C12 phenyl rings, repectively.

Related literature top

For general background to and the coordination environment of triphenyltin(IV) carboxylate complexes, see: Yeap & Teoh (2003); Win et al. (2006, 2008, 2011a,b,c). For standard bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title complex was obtained by heating under reflux a 1:1 molar mixture of triphenyltin(IV) hydroxide (0.73 g, 2 mmol) and 5-amino-2-nitrobenzoic acid (0.36 g, 2 mmol) in methanol (50 ml) for 3 h. A clear yellow transparent solution was separated by filtration and kept in a bottle. After a few days, yellow crystals (0.48 g, 89.0 % yield) were collected. Melting point: 442-443 K. Analysis for C₂₅H₂₀N₂O₄Sn: C, 55.89; H, 3.84; N, 5.14 %. Calculated for C₂₅H₂₀N₂O₄Sn: C, 56.53; H, 3.80; N, 5.27 %.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The polymeric structure of the title compound, viewed along the c axis, showing one-dimensional chains along [010].
	Fig. 3. The crystal packing of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

catena-Poly[[triphenyltin(IV)]-µ-5-amino-2-nitrobenzoato- κ²O¹:O^1'] top

Crystal data top

[Sn(C₆H₅)₃(C₇H₅N₂O₄)]	F(000) = 1064
M_r = 531.12	D_x = 1.595 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9281 reflections
a = 10.9752 (1) Å	θ = 2.4–32.7°
b = 11.8342 (1) Å	µ = 1.19 mm⁻¹
c = 17.4160 (2) Å	T = 100 K
β = 102.164 (1)°	Block, yellow
V = 2211.25 (4) Å³	0.37 × 0.25 × 0.22 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7981 independent reflections
Radiation source: fine-focus sealed tube	7370 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 32.7°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
T_min = 0.671, T_max = 0.783	k = −17→15
27219 measured reflections	l = −24→26

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.046	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0187P)² + 0.9636P] where P = (F_o² + 2F_c²)/3
7981 reflections	(Δ/σ)_max = 0.003
297 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[Sn(C₆H₅)₃(C₇H₅N₂O₄)]	V = 2211.25 (4) Å³
M_r = 531.12	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9752 (1) Å	µ = 1.19 mm⁻¹
b = 11.8342 (1) Å	T = 100 K
c = 17.4160 (2) Å	0.37 × 0.25 × 0.22 mm
β = 102.164 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7981 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	7370 reflections with I > 2σ(I)
T_min = 0.671, T_max = 0.783	R_int = 0.017
27219 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	0 restraints
wR(F²) = 0.046	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.51 e Å⁻³
7981 reflections	Δρ_min = −0.54 e Å⁻³
297 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

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

	x	y	z	U_iso*/U_eq
Sn1	0.980205 (6)	0.157183 (6)	0.217102 (4)	0.01124 (2)
O1	0.93081 (8)	0.32432 (7)	0.16122 (5)	0.01487 (14)
O2	0.97650 (7)	0.46996 (7)	0.24440 (4)	0.01352 (14)
O3	0.70740 (8)	0.38800 (8)	0.21137 (5)	0.02102 (17)
O4	0.53208 (8)	0.43580 (10)	0.13585 (6)	0.0329 (2)
N1	0.89051 (11)	0.67399 (10)	−0.04786 (6)	0.0218 (2)
N2	0.64692 (9)	0.43960 (9)	0.15452 (6)	0.01829 (18)
C1	0.87574 (10)	0.17504 (9)	0.30535 (6)	0.01377 (18)
C2	0.89877 (11)	0.25962 (10)	0.36218 (7)	0.0193 (2)
H2A	0.9597	0.3158	0.3599	0.023*
C3	0.83296 (13)	0.26235 (12)	0.42251 (7)	0.0243 (2)
H3A	0.8496	0.3199	0.4613	0.029*
C4	0.74309 (12)	0.18074 (12)	0.42582 (7)	0.0247 (2)
H4A	0.6988	0.1823	0.4672	0.030*
C5	0.71792 (11)	0.09704 (12)	0.36888 (7)	0.0224 (2)
H5A	0.6557	0.0419	0.3708	0.027*
C6	0.78424 (10)	0.09427 (10)	0.30890 (7)	0.0176 (2)
H6A	0.7670	0.0368	0.2700	0.021*
C7	0.86334 (10)	0.08532 (9)	0.11625 (6)	0.01378 (18)
C8	0.73920 (10)	0.12127 (11)	0.09743 (7)	0.0191 (2)
H8A	0.7118	0.1796	0.1272	0.023*
C9	0.65528 (12)	0.07180 (14)	0.03508 (7)	0.0276 (3)
H9A	0.5712	0.0969	0.0222	0.033*
C10	0.69493 (13)	−0.01430 (14)	−0.00817 (8)	0.0293 (3)
H10A	0.6375	−0.0486	−0.0502	0.035*
C11	0.81737 (14)	−0.05009 (11)	0.00968 (7)	0.0257 (3)
H11A	0.8442	−0.1089	−0.0200	0.031*
C12	0.90166 (12)	0.00017 (10)	0.07139 (7)	0.0186 (2)
H12A	0.9861	−0.0239	0.0830	0.022*
C13	1.17373 (10)	0.19205 (10)	0.23296 (6)	0.01591 (19)
C14	1.25426 (11)	0.11915 (12)	0.20473 (7)	0.0212 (2)
H14A	1.2224	0.0527	0.1770	0.025*
C15	1.38145 (12)	0.14349 (14)	0.21712 (8)	0.0290 (3)
H15A	1.4356	0.0938	0.1974	0.035*
C16	1.42905 (12)	0.23968 (14)	0.25801 (10)	0.0352 (4)
H16A	1.5155	0.2561	0.2661	0.042*
C17	1.34983 (13)	0.31200 (13)	0.28711 (12)	0.0383 (4)
H17A	1.3825	0.3774	0.3158	0.046*
C18	1.22256 (11)	0.28880 (11)	0.27429 (9)	0.0271 (3)
H18A	1.1687	0.3391	0.2938	0.032*
C19	0.92115 (9)	0.42633 (9)	0.18082 (6)	0.01185 (17)
C20	0.84255 (9)	0.49904 (9)	0.11779 (6)	0.01259 (17)
C21	0.90148 (10)	0.55602 (9)	0.06630 (6)	0.01415 (18)
H21A	0.9895	0.5512	0.0730	0.017*
C22	0.83273 (11)	0.62117 (10)	0.00411 (6)	0.01612 (19)
C23	0.70317 (11)	0.63147 (11)	−0.00281 (7)	0.0196 (2)
H23A	0.6562	0.6784	−0.0425	0.024*
C24	0.64407 (10)	0.57407 (11)	0.04748 (7)	0.0194 (2)
H24A	0.5564	0.5806	0.0420	0.023*
C25	0.71282 (10)	0.50604 (10)	0.10674 (6)	0.01502 (19)
H1N1	0.8472 (16)	0.6975 (16)	−0.0914 (11)	0.028 (4)*
H2N1	0.9684 (18)	0.6650 (15)	−0.0455 (11)	0.032 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01332 (3)	0.00974 (4)	0.01053 (3)	−0.00065 (2)	0.00225 (2)	−0.00024 (2)
O1	0.0199 (3)	0.0093 (4)	0.0152 (3)	0.0003 (3)	0.0032 (3)	0.0005 (3)
O2	0.0169 (3)	0.0107 (4)	0.0122 (3)	−0.0003 (3)	0.0013 (2)	0.0001 (3)
O3	0.0179 (4)	0.0240 (5)	0.0210 (4)	0.0006 (3)	0.0037 (3)	0.0069 (3)
O4	0.0126 (4)	0.0446 (7)	0.0399 (5)	−0.0017 (4)	0.0019 (4)	0.0139 (5)
N1	0.0300 (5)	0.0202 (5)	0.0158 (4)	0.0032 (4)	0.0060 (4)	0.0064 (4)
N2	0.0147 (4)	0.0192 (5)	0.0207 (4)	0.0001 (3)	0.0032 (3)	0.0007 (4)
C1	0.0163 (4)	0.0126 (5)	0.0127 (4)	0.0008 (3)	0.0035 (3)	0.0008 (3)
C2	0.0264 (5)	0.0143 (5)	0.0187 (5)	−0.0024 (4)	0.0080 (4)	−0.0027 (4)
C3	0.0340 (6)	0.0220 (6)	0.0194 (5)	0.0012 (5)	0.0109 (5)	−0.0050 (4)
C4	0.0279 (6)	0.0298 (7)	0.0198 (5)	0.0035 (5)	0.0125 (4)	0.0028 (5)
C5	0.0205 (5)	0.0256 (6)	0.0225 (5)	−0.0029 (4)	0.0076 (4)	0.0041 (5)
C6	0.0179 (4)	0.0177 (5)	0.0169 (5)	−0.0020 (4)	0.0033 (4)	−0.0007 (4)
C7	0.0180 (4)	0.0110 (5)	0.0121 (4)	−0.0022 (4)	0.0025 (3)	0.0001 (3)
C8	0.0170 (4)	0.0239 (6)	0.0164 (5)	−0.0026 (4)	0.0037 (4)	−0.0024 (4)
C9	0.0190 (5)	0.0422 (8)	0.0203 (5)	−0.0086 (5)	0.0014 (4)	−0.0037 (5)
C10	0.0326 (6)	0.0358 (8)	0.0186 (5)	−0.0178 (6)	0.0030 (5)	−0.0081 (5)
C11	0.0426 (7)	0.0173 (6)	0.0176 (5)	−0.0072 (5)	0.0075 (5)	−0.0059 (4)
C12	0.0282 (5)	0.0120 (5)	0.0155 (5)	0.0010 (4)	0.0041 (4)	−0.0004 (4)
C13	0.0152 (4)	0.0144 (5)	0.0174 (5)	−0.0005 (4)	0.0019 (3)	0.0052 (4)
C14	0.0192 (5)	0.0284 (7)	0.0166 (5)	0.0016 (4)	0.0052 (4)	0.0017 (4)
C15	0.0184 (5)	0.0444 (9)	0.0259 (6)	0.0052 (5)	0.0082 (4)	0.0084 (6)
C16	0.0165 (5)	0.0367 (9)	0.0500 (9)	−0.0036 (5)	0.0012 (5)	0.0195 (7)
C17	0.0202 (6)	0.0196 (7)	0.0683 (11)	−0.0053 (5)	−0.0064 (6)	0.0053 (7)
C18	0.0180 (5)	0.0140 (6)	0.0453 (8)	−0.0004 (4)	−0.0020 (5)	0.0000 (5)
C19	0.0123 (4)	0.0114 (5)	0.0124 (4)	−0.0002 (3)	0.0039 (3)	0.0015 (3)
C20	0.0154 (4)	0.0096 (5)	0.0120 (4)	0.0007 (3)	0.0013 (3)	−0.0010 (3)
C21	0.0175 (4)	0.0120 (5)	0.0126 (4)	0.0011 (4)	0.0023 (3)	0.0004 (3)
C22	0.0231 (5)	0.0122 (5)	0.0125 (4)	0.0012 (4)	0.0025 (4)	0.0000 (4)
C23	0.0221 (5)	0.0173 (5)	0.0170 (5)	0.0038 (4)	−0.0017 (4)	0.0031 (4)
C24	0.0163 (4)	0.0194 (6)	0.0202 (5)	0.0030 (4)	−0.0012 (4)	0.0016 (4)
C25	0.0154 (4)	0.0137 (5)	0.0152 (4)	0.0002 (4)	0.0016 (3)	0.0003 (4)

Geometric parameters (Å, º) top

Sn1—C1	2.1129 (11)	C9—C10	1.390 (2)
Sn1—C7	2.1222 (10)	C9—H9A	0.9500
Sn1—C13	2.1239 (11)	C10—C11	1.381 (2)
Sn1—O1	2.2205 (8)	C10—H10A	0.9500
Sn1—O2ⁱ	2.3345 (8)	C11—C12	1.3949 (17)
O1—C19	1.2651 (13)	C11—H11A	0.9500
O2—C19	1.2563 (12)	C12—H12A	0.9500
O2—Sn1ⁱⁱ	2.3345 (8)	C13—C14	1.3965 (17)
O3—N2	1.2315 (13)	C13—C18	1.3978 (18)
O4—N2	1.2344 (12)	C14—C15	1.3968 (17)
N1—C22	1.3616 (15)	C14—H14A	0.9500
N1—H1N1	0.852 (18)	C15—C16	1.385 (2)
N1—H2N1	0.853 (19)	C15—H15A	0.9500
N2—C25	1.4447 (15)	C16—C17	1.390 (2)
C1—C2	1.3928 (16)	C16—H16A	0.9500
C1—C6	1.3972 (16)	C17—C18	1.3947 (18)
C2—C3	1.3952 (17)	C17—H17A	0.9500
C2—H2A	0.9500	C18—H18A	0.9500
C3—C4	1.390 (2)	C19—C20	1.5135 (14)
C3—H3A	0.9500	C20—C21	1.3862 (15)
C4—C5	1.3876 (19)	C20—C25	1.3984 (14)
C4—H4A	0.9500	C21—C22	1.4116 (15)
C5—C6	1.3937 (16)	C21—H21A	0.9500
C5—H5A	0.9500	C22—C23	1.4068 (16)
C6—H6A	0.9500	C23—C24	1.3742 (17)
C7—C12	1.3933 (16)	C23—H23A	0.9500
C7—C8	1.3988 (15)	C24—C25	1.3982 (15)
C8—C9	1.3960 (16)	C24—H24A	0.9500
C8—H8A	0.9500

C1—Sn1—C7	108.43 (4)	C9—C10—H10A	119.9
C1—Sn1—C13	124.55 (4)	C10—C11—C12	119.92 (12)
C7—Sn1—C13	126.79 (4)	C10—C11—H11A	120.0
C1—Sn1—O1	96.31 (4)	C12—C11—H11A	120.0
C7—Sn1—O1	86.85 (4)	C7—C12—C11	120.73 (11)
C13—Sn1—O1	91.67 (4)	C7—C12—H12A	119.6
C1—Sn1—O2ⁱ	89.71 (4)	C11—C12—H12A	119.6
C7—Sn1—O2ⁱ	84.74 (3)	C14—C13—C18	119.01 (11)
C13—Sn1—O2ⁱ	90.55 (4)	C14—C13—Sn1	121.60 (9)
O1—Sn1—O2ⁱ	170.88 (3)	C18—C13—Sn1	119.37 (9)
C19—O1—Sn1	139.32 (7)	C13—C14—C15	120.28 (13)
C19—O2—Sn1ⁱⁱ	132.42 (7)	C13—C14—H14A	119.9
C22—N1—H1N1	119.4 (12)	C15—C14—H14A	119.9
C22—N1—H2N1	120.9 (13)	C16—C15—C14	120.35 (13)
H1N1—N1—H2N1	116.6 (17)	C16—C15—H15A	119.8
O3—N2—O4	122.76 (11)	C14—C15—H15A	119.8
O3—N2—C25	118.84 (9)	C15—C16—C17	119.76 (12)
O4—N2—C25	118.39 (10)	C15—C16—H16A	120.1
C2—C1—C6	119.00 (10)	C17—C16—H16A	120.1
C2—C1—Sn1	122.94 (8)	C16—C17—C18	120.20 (15)
C6—C1—Sn1	117.97 (8)	C16—C17—H17A	119.9
C1—C2—C3	120.43 (11)	C18—C17—H17A	119.9
C1—C2—H2A	119.8	C17—C18—C13	120.40 (14)
C3—C2—H2A	119.8	C17—C18—H18A	119.8
C4—C3—C2	119.97 (12)	C13—C18—H18A	119.8
C4—C3—H3A	120.0	O2—C19—O1	125.29 (10)
C2—C3—H3A	120.0	O2—C19—C20	120.10 (10)
C5—C4—C3	120.16 (11)	O1—C19—C20	114.46 (9)
C5—C4—H4A	119.9	C21—C20—C25	118.85 (9)
C3—C4—H4A	119.9	C21—C20—C19	118.26 (9)
C4—C5—C6	119.71 (12)	C25—C20—C19	122.80 (9)
C4—C5—H5A	120.1	C20—C21—C22	121.02 (10)
C6—C5—H5A	120.1	C20—C21—H21A	119.5
C5—C6—C1	120.71 (11)	C22—C21—H21A	119.5
C5—C6—H6A	119.6	N1—C22—C23	120.48 (11)
C1—C6—H6A	119.6	N1—C22—C21	120.82 (11)
C12—C7—C8	118.86 (10)	C23—C22—C21	118.70 (10)
C12—C7—Sn1	123.56 (8)	C24—C23—C22	120.46 (10)
C8—C7—Sn1	117.46 (8)	C24—C23—H23A	119.8
C9—C8—C7	120.34 (12)	C22—C23—H23A	119.8
C9—C8—H8A	119.8	C23—C24—C25	120.09 (10)
C7—C8—H8A	119.8	C23—C24—H24A	120.0
C10—C9—C8	119.88 (12)	C25—C24—H24A	120.0
C10—C9—H9A	120.1	C24—C25—C20	120.74 (10)
C8—C9—H9A	120.1	C24—C25—N2	118.73 (10)
C11—C10—C9	120.25 (11)	C20—C25—N2	120.48 (9)
C11—C10—H10A	119.9

C1—Sn1—O1—C19	44.23 (11)	O2ⁱ—Sn1—C13—C14	45.61 (9)
C7—Sn1—O1—C19	152.44 (11)	C1—Sn1—C13—C18	−42.79 (11)
C13—Sn1—O1—C19	−80.80 (11)	C7—Sn1—C13—C18	143.36 (9)
C7—Sn1—C1—C2	−150.32 (9)	O1—Sn1—C13—C18	56.05 (10)
C13—Sn1—C1—C2	34.87 (11)	O2ⁱ—Sn1—C13—C18	−132.81 (10)
O1—Sn1—C1—C2	−61.55 (10)	C18—C13—C14—C15	−0.60 (18)
O2ⁱ—Sn1—C1—C2	125.33 (9)	Sn1—C13—C14—C15	−179.01 (9)
C7—Sn1—C1—C6	33.28 (10)	C13—C14—C15—C16	0.5 (2)
C13—Sn1—C1—C6	−141.54 (8)	C14—C15—C16—C17	0.3 (2)
O1—Sn1—C1—C6	122.05 (8)	C15—C16—C17—C18	−0.9 (2)
O2ⁱ—Sn1—C1—C6	−51.08 (9)	C16—C17—C18—C13	0.8 (2)
C6—C1—C2—C3	1.14 (17)	C14—C13—C18—C17	0.0 (2)
Sn1—C1—C2—C3	−175.23 (9)	Sn1—C13—C18—C17	178.42 (12)
C1—C2—C3—C4	−0.5 (2)	Sn1ⁱⁱ—O2—C19—O1	161.05 (8)
C2—C3—C4—C5	−0.5 (2)	Sn1ⁱⁱ—O2—C19—C20	−14.22 (14)
C3—C4—C5—C6	0.8 (2)	Sn1—O1—C19—O2	23.95 (17)
C4—C5—C6—C1	−0.13 (18)	Sn1—O1—C19—C20	−160.54 (8)
C2—C1—C6—C5	−0.84 (17)	O2—C19—C20—C21	84.57 (13)
Sn1—C1—C6—C5	175.71 (9)	O1—C19—C20—C21	−91.18 (12)
C1—Sn1—C7—C12	−137.16 (9)	O2—C19—C20—C25	−99.06 (12)
C13—Sn1—C7—C12	37.51 (11)	O1—C19—C20—C25	85.18 (13)
O1—Sn1—C7—C12	127.23 (10)	C25—C20—C21—C22	0.66 (16)
O2ⁱ—Sn1—C7—C12	−49.23 (9)	C19—C20—C21—C22	177.17 (10)
C1—Sn1—C7—C8	38.72 (10)	C20—C21—C22—N1	−177.84 (11)
C13—Sn1—C7—C8	−146.61 (8)	C20—C21—C22—C23	2.76 (17)
O1—Sn1—C7—C8	−56.89 (9)	N1—C22—C23—C24	177.06 (12)
O2ⁱ—Sn1—C7—C8	126.65 (9)	C21—C22—C23—C24	−3.54 (18)
C12—C7—C8—C9	0.47 (18)	C22—C23—C24—C25	0.88 (19)
Sn1—C7—C8—C9	−175.60 (10)	C23—C24—C25—C20	2.66 (18)
C7—C8—C9—C10	0.5 (2)	C23—C24—C25—N2	−175.00 (11)
C8—C9—C10—C11	−0.8 (2)	C21—C20—C25—C24	−3.40 (16)
C9—C10—C11—C12	0.1 (2)	C19—C20—C25—C24	−179.75 (10)
C8—C7—C12—C11	−1.23 (17)	C21—C20—C25—N2	174.21 (10)
Sn1—C7—C12—C11	174.60 (9)	C19—C20—C25—N2	−2.13 (16)
C10—C11—C12—C7	0.96 (19)	O3—N2—C25—C24	−173.22 (11)
C1—Sn1—C13—C14	135.63 (9)	O4—N2—C25—C24	7.77 (17)
C7—Sn1—C13—C14	−38.23 (11)	O3—N2—C25—C20	9.12 (16)
O1—Sn1—C13—C14	−125.54 (9)	O4—N2—C25—C20	−169.90 (11)

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N1···O1ⁱⁱⁱ	0.85 (2)	2.498 (19)	3.0619 (14)	124.3 (15)
C5—H5A···O4^iv	0.95	2.40	3.3288 (16)	167
C3—H3A···Cg2^v	0.95	2.58	3.4430 (14)	152
C21—H21A···Cg1ⁱⁱ	0.95	2.70	3.4669 (12)	138

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

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃(C₇H₅N₂O₄)]
M_r	531.12
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.9752 (1), 11.8342 (1), 17.4160 (2)
β (°)	102.164 (1)
V (Å³)	2211.25 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.19
Crystal size (mm)	0.37 × 0.25 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.671, 0.783
No. of measured, independent and observed [I > 2σ(I)] reflections	27219, 7981, 7370
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.759

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.046, 1.07
No. of reflections	7981
No. of parameters	297
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.54

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N1···O1ⁱ	0.85 (2)	2.498 (19)	3.0619 (14)	124.3 (15)
C5—H5A···O4ⁱⁱ	0.95	2.40	3.3288 (16)	167
C3—H3A···Cg2ⁱⁱⁱ	0.95	2.58	3.4430 (14)	152
C21—H21A···Cg1^iv	0.95	2.70	3.4669 (12)	138

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

Footnotes

‡Thomson Reuters ResearcherID: A-5525-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors would like to thank Universiti Tunku Abdul Rahman (UTAR) for the UTAR Research Fund (project No. IPSR/RMC/UTARRF/C1–C11/C07) and Universiti Sains Malaysia (USM) for providing research facilities. HKF and CKQ also thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

References

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Volume 67| Part 9| September 2011| Pages m1276-m1277

doi:10.1107/S1600536811033332

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