(4-Chloro-3-nitro-benzoato)triphenyl-tin(IV).

In the title compound, [Sn(C(6)H(5))(3)(C(7)H(3)ClNO(4))], the four-coordinate Sn(IV) atom exists in a distorted tetra-hedral geometry, formed by a monodentate carboxyl-ate group and three phenyl rings. The conformation is stabilized by an intra-molecular C-H⋯O hydrogen bond, which generates an S(5) ring. The aromatic ring of the 4-chloro-3-nitro-benzoate ligand makes dihedral angles of 75.64 (12), 64.37 (12) and 2.97 (12)° with the three phenyl ligands. The O atoms of the nitro group are disordered over two sets of sites in a 0.817 (5):0.183 (5) ratio. In the crystal, mol-ecules are linked via inter-molecular C-H⋯O hydrogen bonds into chains running parallel to [010].

Related literature

For general background to and the metal coordination environment of the title complex, see: Win et al. (2008 ▶, 2010 ▶, 2011a ▶,b ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

[Sn(C6H5)3(C7H3ClNO4)]

M = 550.54

Monoclinic,

a = 12.3926 (2) Å

b = 8.8033 (1) Å

c = 21.5592 (3) Å

β = 103.217 (1)°

V = 2289.72 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.26 mm−1

T = 100 K

0.35 × 0.31 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.668, T max = 0.807

23882 measured reflections

5204 independent reflections

4817 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.056

S = 1.11

5204 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.68 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAIn class="Chemical">NT (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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103282X/hb6362sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103282X/hb6362Isup2.hkl

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

[Sn(C6H5)3(C7H3ClNO4)]	F(000) = 1096
Mr = 550.54	Dx = 1.597 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9115 reflections
a = 12.3926 (2) Å	θ = 2.5–32.7°
b = 8.8033 (1) Å	µ = 1.26 mm−1
c = 21.5592 (3) Å	T = 100 K
β = 103.217 (1)°	Block, colourless
V = 2289.72 (6) Å3	0.35 × 0.31 × 0.18 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	5204 independent reflections
Radiation source: fine-focus sealed tube	4817 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→16
Tmin = 0.668, Tmax = 0.807	k = −11→9
23882 measured reflections	l = −28→27

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0116P)2 + 3.5862P] where P = (Fo2 + 2Fc2)/3
5204 reflections	(Δ/σ)max = 0.001
308 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.68 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sn1	0.364093 (12)	0.404888 (17)	0.369328 (7)	0.01672 (5)
Cl1	0.01735 (7)	0.74667 (9)	0.64665 (4)	0.0474 (2)
O1	0.29596 (13)	0.45731 (19)	0.44511 (8)	0.0217 (3)
O2	0.18430 (14)	0.6075 (2)	0.37524 (8)	0.0256 (4)
O3	−0.1368 (2)	0.8214 (4)	0.45615 (14)	0.0435 (8)	0.817 (5)
O4	−0.0736 (2)	0.9462 (3)	0.54411 (12)	0.0375 (7)	0.817 (5)
O3X	−0.0894 (9)	0.9151 (14)	0.4504 (6)	0.038 (3)	0.183 (5)
O4X	−0.1525 (9)	0.8071 (14)	0.5262 (7)	0.049 (4)	0.183 (5)
N1	−0.07089 (19)	0.8404 (3)	0.50478 (13)	0.0344 (5)
C1	0.22638 (19)	0.1332 (3)	0.30822 (12)	0.0233 (5)
H1A	0.2741	0.0800	0.3405	0.028*
C2	0.1424 (2)	0.0565 (3)	0.26581 (12)	0.0293 (6)
H2A	0.1340	−0.0478	0.2699	0.035*
C3	0.0713 (2)	0.1352 (3)	0.21756 (13)	0.0326 (6)
H3A	0.0149	0.0840	0.1895	0.039*
C4	0.0845 (2)	0.2900 (3)	0.21118 (12)	0.0311 (6)
H4A	0.0374	0.3426	0.1785	0.037*
C5	0.1678 (2)	0.3671 (3)	0.25337 (11)	0.0258 (5)
H5A	0.1761	0.4712	0.2489	0.031*
C6	0.23910 (18)	0.2891 (3)	0.30242 (11)	0.0200 (5)
C7	0.3731 (2)	0.7235 (3)	0.30473 (11)	0.0259 (5)
H7A	0.2964	0.7249	0.2987	0.031*
C8	0.4268 (2)	0.8430 (3)	0.28291 (12)	0.0293 (6)
H8A	0.3858	0.9241	0.2621	0.035*
C9	0.5414 (2)	0.8432 (3)	0.29180 (12)	0.0283 (6)
H9A	0.5769	0.9245	0.2774	0.034*
C10	0.6026 (2)	0.7222 (3)	0.32206 (12)	0.0281 (5)
H10A	0.6793	0.7216	0.3280	0.034*
C11	0.5490 (2)	0.6014 (3)	0.34361 (11)	0.0234 (5)
H11A	0.5904	0.5197	0.3636	0.028*
C12	0.43383 (19)	0.6006 (3)	0.33577 (10)	0.0200 (5)
C13	0.5609 (2)	0.1802 (3)	0.39217 (12)	0.0249 (5)
H13A	0.5514	0.1861	0.3482	0.030*
C14	0.6447 (2)	0.0898 (3)	0.42741 (13)	0.0286 (5)
H14A	0.6911	0.0358	0.4070	0.034*
C15	0.6592 (2)	0.0801 (3)	0.49280 (13)	0.0281 (5)
H15A	0.7153	0.0196	0.5165	0.034*
C16	0.5902 (2)	0.1608 (3)	0.52298 (12)	0.0275 (5)
H16A	0.5999	0.1538	0.5670	0.033*
C17	0.50684 (19)	0.2517 (3)	0.48821 (11)	0.0228 (5)
H17A	0.4613	0.3061	0.5090	0.027*
C18	0.49066 (18)	0.2622 (2)	0.42193 (11)	0.0183 (4)
C19	0.21426 (18)	0.5547 (3)	0.42882 (11)	0.0199 (5)
C20	0.16128 (17)	0.5965 (3)	0.48230 (11)	0.0188 (4)
C21	0.07045 (19)	0.6930 (3)	0.47042 (12)	0.0219 (5)
H21A	0.0401	0.7267	0.4292	0.026*
C22	0.02544 (19)	0.7387 (3)	0.52057 (12)	0.0230 (5)
C23	0.0696 (2)	0.6910 (3)	0.58240 (12)	0.0261 (5)
C24	0.1580 (2)	0.5903 (3)	0.59346 (12)	0.0285 (5)
H24A	0.1873	0.5546	0.6345	0.034*
C25	0.20268 (19)	0.5428 (3)	0.54347 (11)	0.0227 (5)
H25A	0.2612	0.4741	0.5511	0.027*

	U11	U22	U33	U12	U13	U23
Sn1	0.01539 (8)	0.01828 (8)	0.01466 (8)	0.00306 (6)	−0.00037 (6)	−0.00178 (6)
Cl1	0.0558 (5)	0.0539 (5)	0.0429 (4)	0.0225 (4)	0.0327 (4)	0.0056 (4)
O1	0.0198 (8)	0.0248 (8)	0.0196 (9)	0.0073 (7)	0.0027 (7)	−0.0023 (7)
O2	0.0247 (8)	0.0332 (10)	0.0166 (9)	0.0060 (8)	−0.0003 (7)	−0.0012 (7)
O3	0.0263 (14)	0.0471 (19)	0.0520 (18)	0.0166 (13)	−0.0017 (13)	0.0013 (14)
O4	0.0418 (14)	0.0267 (13)	0.0495 (16)	0.0145 (10)	0.0218 (12)	0.0025 (11)
O3X	0.029 (6)	0.032 (7)	0.049 (7)	0.016 (5)	0.001 (5)	−0.003 (5)
O4X	0.029 (6)	0.043 (7)	0.085 (10)	0.008 (5)	0.032 (6)	0.005 (6)
N1	0.0292 (12)	0.0284 (12)	0.0495 (16)	0.0116 (10)	0.0168 (12)	0.0074 (11)
C1	0.0188 (11)	0.0301 (13)	0.0201 (12)	0.0018 (10)	0.0028 (9)	−0.0037 (10)
C2	0.0245 (13)	0.0318 (14)	0.0324 (15)	−0.0065 (11)	0.0080 (11)	−0.0114 (11)
C3	0.0187 (12)	0.0471 (17)	0.0305 (15)	−0.0032 (11)	0.0022 (11)	−0.0175 (12)
C4	0.0211 (12)	0.0506 (17)	0.0172 (13)	0.0091 (12)	−0.0047 (10)	−0.0092 (12)
C5	0.0240 (12)	0.0320 (14)	0.0206 (13)	0.0043 (10)	0.0032 (10)	−0.0042 (10)
C6	0.0148 (10)	0.0292 (12)	0.0148 (11)	0.0020 (9)	0.0010 (9)	−0.0059 (10)
C7	0.0270 (12)	0.0304 (13)	0.0201 (12)	0.0085 (11)	0.0050 (10)	0.0011 (10)
C8	0.0425 (15)	0.0243 (12)	0.0230 (13)	0.0103 (11)	0.0111 (12)	0.0061 (10)
C9	0.0423 (15)	0.0237 (12)	0.0209 (13)	−0.0029 (11)	0.0114 (11)	0.0000 (10)
C10	0.0263 (13)	0.0318 (14)	0.0246 (13)	−0.0044 (11)	0.0026 (10)	−0.0015 (11)
C11	0.0254 (12)	0.0237 (12)	0.0182 (12)	0.0018 (10)	−0.0008 (9)	0.0005 (10)
C12	0.0248 (11)	0.0200 (11)	0.0139 (11)	0.0019 (9)	0.0017 (9)	−0.0009 (9)
C13	0.0254 (12)	0.0253 (13)	0.0237 (13)	0.0042 (10)	0.0048 (10)	−0.0006 (10)
C14	0.0231 (12)	0.0262 (12)	0.0360 (15)	0.0079 (10)	0.0059 (11)	−0.0029 (11)
C15	0.0207 (12)	0.0214 (12)	0.0365 (15)	0.0040 (10)	−0.0052 (10)	0.0027 (11)
C16	0.0296 (13)	0.0287 (13)	0.0194 (13)	0.0038 (11)	−0.0043 (10)	0.0013 (10)
C17	0.0221 (11)	0.0219 (12)	0.0232 (13)	0.0039 (9)	0.0026 (10)	−0.0026 (10)
C18	0.0154 (10)	0.0162 (10)	0.0210 (12)	−0.0002 (8)	−0.0007 (9)	−0.0006 (9)
C19	0.0162 (10)	0.0204 (11)	0.0209 (12)	−0.0004 (9)	−0.0003 (9)	−0.0061 (9)
C20	0.0148 (10)	0.0182 (10)	0.0219 (12)	−0.0011 (9)	0.0011 (9)	−0.0038 (9)
C21	0.0202 (11)	0.0200 (11)	0.0229 (13)	0.0020 (9)	−0.0001 (9)	0.0016 (10)
C22	0.0169 (11)	0.0169 (11)	0.0356 (14)	0.0025 (9)	0.0067 (10)	−0.0010 (10)
C23	0.0262 (12)	0.0265 (13)	0.0296 (14)	0.0016 (10)	0.0148 (11)	−0.0003 (10)
C24	0.0276 (12)	0.0350 (14)	0.0235 (13)	0.0080 (11)	0.0071 (10)	0.0028 (11)
C25	0.0172 (11)	0.0257 (12)	0.0244 (13)	0.0052 (9)	0.0032 (9)	−0.0010 (10)

Sn1—O1	2.0558 (15)	C9—C10	1.382 (4)
Sn1—C6	2.121 (2)	C9—H9A	0.9300
Sn1—C18	2.124 (2)	C10—C11	1.389 (3)
Sn1—C12	2.127 (2)	C10—H10A	0.9300
Cl1—C23	1.729 (2)	C11—C12	1.398 (3)
O1—C19	1.311 (3)	C11—H11A	0.9300
O2—C19	1.222 (3)	C13—C14	1.389 (3)
O3—N1	1.185 (3)	C13—C18	1.395 (3)
O4—N1	1.266 (3)	C13—H13A	0.9300
O3X—N1	1.318 (12)	C14—C15	1.383 (4)
O4X—N1	1.239 (10)	C14—H14A	0.9300
N1—C22	1.469 (3)	C15—C16	1.383 (4)
C1—C6	1.390 (3)	C15—H15A	0.9300
C1—C2	1.393 (3)	C16—C17	1.384 (3)
C1—H1A	0.9300	C16—H16A	0.9300
C2—C3	1.385 (4)	C17—C18	1.400 (3)
C2—H2A	0.9300	C17—H17A	0.9300
C3—C4	1.383 (4)	C19—C20	1.497 (3)
C3—H3A	0.9300	C20—C25	1.384 (3)
C4—C5	1.387 (4)	C20—C21	1.387 (3)
C4—H4A	0.9300	C21—C22	1.385 (3)
C5—C6	1.394 (3)	C21—H21A	0.9300
C5—H5A	0.9300	C22—C23	1.385 (4)
C7—C8	1.384 (4)	C23—C24	1.387 (3)
C7—C12	1.398 (3)	C24—C25	1.384 (3)
C7—H7A	0.9300	C24—H24A	0.9300
C8—C9	1.388 (4)	C25—H25A	0.9300
C8—H8A	0.9300
O1—Sn1—C6	106.24 (7)	C11—C10—H10A	120.2
O1—Sn1—C18	95.50 (7)	C10—C11—C12	121.1 (2)
C6—Sn1—C18	114.46 (9)	C10—C11—H11A	119.4
O1—Sn1—C12	111.17 (8)	C12—C11—H11A	119.4
C6—Sn1—C12	116.64 (9)	C7—C12—C11	118.5 (2)
C18—Sn1—C12	110.66 (9)	C7—C12—Sn1	125.01 (18)
C19—O1—Sn1	111.47 (14)	C11—C12—Sn1	116.48 (17)
O3—N1—O4X	80.8 (7)	C14—C13—C18	120.8 (2)
O3—N1—O4	125.3 (3)	C14—C13—H13A	119.6
O4X—N1—O4	77.0 (6)	C18—C13—H13A	119.6
O3—N1—O3X	48.6 (5)	C15—C14—C13	120.0 (2)
O4X—N1—O3X	117.3 (8)	C15—C14—H14A	120.0
O4—N1—O3X	101.7 (5)	C13—C14—H14A	120.0
O3—N1—C22	118.6 (2)	C14—C15—C16	119.9 (2)
O4X—N1—C22	117.3 (6)	C14—C15—H15A	120.1
O4—N1—C22	116.0 (2)	C16—C15—H15A	120.1
O3X—N1—C22	118.5 (5)	C15—C16—C17	120.5 (2)
C6—C1—C2	120.2 (2)	C15—C16—H16A	119.8
C6—C1—H1A	119.9	C17—C16—H16A	119.8
C2—C1—H1A	119.9	C16—C17—C18	120.4 (2)
C3—C2—C1	120.1 (3)	C16—C17—H17A	119.8
C3—C2—H2A	119.9	C18—C17—H17A	119.8
C1—C2—H2A	119.9	C13—C18—C17	118.5 (2)
C4—C3—C2	119.9 (2)	C13—C18—Sn1	121.51 (17)
C4—C3—H3A	120.1	C17—C18—Sn1	120.00 (16)
C2—C3—H3A	120.1	O2—C19—O1	123.5 (2)
C3—C4—C5	120.3 (3)	O2—C19—C20	122.8 (2)
C3—C4—H4A	119.9	O1—C19—C20	113.7 (2)
C5—C4—H4A	119.9	C25—C20—C21	119.6 (2)
C4—C5—C6	120.2 (3)	C25—C20—C19	121.2 (2)
C4—C5—H5A	119.9	C21—C20—C19	119.3 (2)
C6—C5—H5A	119.9	C22—C21—C20	119.2 (2)
C1—C6—C5	119.3 (2)	C22—C21—H21A	120.4
C1—C6—Sn1	119.58 (18)	C20—C21—H21A	120.4
C5—C6—Sn1	121.11 (18)	C21—C22—C23	121.5 (2)
C8—C7—C12	120.2 (2)	C21—C22—N1	116.6 (2)
C8—C7—H7A	119.9	C23—C22—N1	121.9 (2)
C12—C7—H7A	119.9	C22—C23—C24	118.8 (2)
C7—C8—C9	120.6 (2)	C22—C23—Cl1	123.18 (19)
C7—C8—H8A	119.7	C24—C23—Cl1	118.0 (2)
C9—C8—H8A	119.7	C25—C24—C23	120.0 (2)
C10—C9—C8	119.9 (2)	C25—C24—H24A	120.0
C10—C9—H9A	120.1	C23—C24—H24A	120.0
C8—C9—H9A	120.1	C24—C25—C20	120.8 (2)
C9—C10—C11	119.7 (2)	C24—C25—H25A	119.6
C9—C10—H10A	120.2	C20—C25—H25A	119.6
C6—Sn1—O1—C19	−65.58 (16)	C14—C13—C18—Sn1	178.65 (19)
C18—Sn1—O1—C19	176.95 (15)	C16—C17—C18—C13	−0.6 (4)
C12—Sn1—O1—C19	62.28 (16)	C16—C17—C18—Sn1	−179.01 (18)
C6—C1—C2—C3	0.2 (3)	O1—Sn1—C18—C13	174.44 (19)
C1—C2—C3—C4	0.6 (4)	C6—Sn1—C18—C13	63.8 (2)
C2—C3—C4—C5	−0.8 (4)	C12—Sn1—C18—C13	−70.5 (2)
C3—C4—C5—C6	0.2 (4)	O1—Sn1—C18—C17	−7.14 (19)
C2—C1—C6—C5	−0.7 (3)	C6—Sn1—C18—C17	−117.78 (18)
C2—C1—C6—Sn1	177.96 (16)	C12—Sn1—C18—C17	107.94 (19)
C4—C5—C6—C1	0.5 (3)	Sn1—O1—C19—O2	−0.7 (3)
C4—C5—C6—Sn1	−178.13 (17)	Sn1—O1—C19—C20	179.81 (14)
O1—Sn1—C6—C1	−85.63 (18)	O2—C19—C20—C25	−175.2 (2)
C18—Sn1—C6—C1	18.4 (2)	O1—C19—C20—C25	4.3 (3)
C12—Sn1—C6—C1	149.83 (17)	O2—C19—C20—C21	3.5 (3)
O1—Sn1—C6—C5	93.03 (18)	O1—C19—C20—C21	−177.0 (2)
C18—Sn1—C6—C5	−162.96 (17)	C25—C20—C21—C22	2.5 (3)
C12—Sn1—C6—C5	−31.5 (2)	C19—C20—C21—C22	−176.3 (2)
C12—C7—C8—C9	−0.4 (4)	C20—C21—C22—C23	0.5 (4)
C7—C8—C9—C10	0.7 (4)	C20—C21—C22—N1	−179.7 (2)
C8—C9—C10—C11	−0.2 (4)	O3—N1—C22—C21	37.1 (4)
C9—C10—C11—C12	−0.6 (4)	O4X—N1—C22—C21	131.5 (8)
C8—C7—C12—C11	−0.5 (3)	O4—N1—C22—C21	−140.2 (2)
C8—C7—C12—Sn1	−177.80 (18)	O3X—N1—C22—C21	−18.8 (7)
C10—C11—C12—C7	1.0 (3)	O3—N1—C22—C23	−143.2 (3)
C10—C11—C12—Sn1	178.53 (18)	O4X—N1—C22—C23	−48.8 (8)
O1—Sn1—C12—C7	−69.0 (2)	O4—N1—C22—C23	39.5 (3)
C6—Sn1—C12—C7	53.0 (2)	O3X—N1—C22—C23	160.9 (7)
C18—Sn1—C12—C7	−173.79 (19)	C21—C22—C23—C24	−2.8 (4)
O1—Sn1—C12—C11	113.67 (17)	N1—C22—C23—C24	177.5 (2)
C6—Sn1—C12—C11	−124.34 (17)	C21—C22—C23—Cl1	179.23 (19)
C18—Sn1—C12—C11	8.8 (2)	N1—C22—C23—Cl1	−0.5 (4)
C18—C13—C14—C15	0.1 (4)	C22—C23—C24—C25	2.0 (4)
C13—C14—C15—C16	−0.1 (4)	Cl1—C23—C24—C25	−179.9 (2)
C14—C15—C16—C17	−0.2 (4)	C23—C24—C25—C20	1.0 (4)
C15—C16—C17—C18	0.6 (4)	C21—C20—C25—C24	−3.2 (4)
C14—C13—C18—C17	0.2 (4)	C19—C20—C25—C24	175.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2i	0.93	2.55	3.346 (3)	144
C17—H17A···O1	0.93	2.56	3.140 (3)	120

Table 1

Selected bond lengths (Å)

Sn1—O1	2.0558 (15)
Sn1—C6	2.121 (2)
Sn1—C18	2.124 (2)
Sn1—C12	2.127 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2i	0.93	2.55	3.346 (3)	144
C17—H17A⋯O1	0.93	2.56	3.140 (3)	120

Symmetry code: (i) .