Bis(5-amino-2-chloro­benzoato-κO)triphenyl­anti­mony(V)

Wen, L.; Yin, H.; Wang, C.

doi:10.1107/S1600536809043578

metal-organic compounds

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Volume 65| Part 11| November 2009| Page m1443

https://doi.org/10.1107/S1600536809043578

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Bis(5-amino-2-chlorobenzoato-κO)triphenylantimony(V)

Liyuan Wen,^a Handong Yin ^a ^* and Chuanhua Wang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 10 October 2009; accepted 22 October 2009; online 28 October 2009)

In the title compound, [Sb(C₆H₅)₃(C₇H₅ClNO₂)₂], the Sb center has a distorted trigonal-bipyramidal geometry, with the O atoms of two carboxylate groups in axial positions and the C atoms of the phenyl groups in equatorial positions. Intramolecular C—H⋯O interactions occur. The molecules are connected by intermolecular N—H⋯O, N—H⋯N and C—H⋯O hydrogen-bonding interactions and C—H⋯π stacking interactions, forming a three-dimensional supramolecular framework

Related literature

For related structures, see: Yin et al. (2009 ); Wang et al. (2005 ).

Experimental

Crystal data

[Sb(C₆H₅)₃(C₇H₅ClNO₂)₂]
M_r = 694.19
Monoclinic, C 2/c
a = 30.683 (3) Å
b = 9.0128 (12) Å
c = 23.096 (3) Å
β = 106.161 (2)°
V = 6134.6 (12) Å³
Z = 8
Mo Kα radiation
μ = 1.11 mm⁻¹
T = 298 K
0.35 × 0.33 × 0.17 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.697, T_max = 0.833
15481 measured reflections
5409 independent reflections
3450 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.087
S = 1.04
5409 reflections
386 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sb1—C21	2.098 (5)
Sb1—C15	2.108 (5)
Sb1—C27	2.109 (5)
Sb1—O3	2.125 (3)
Sb1—O1	2.137 (3)

C21—Sb1—C15	109.59 (19)
C21—Sb1—C27	109.92 (19)
C15—Sb1—C27	140.49 (19)
C21—Sb1—O3	87.33 (16)
C15—Sb1—O3	92.36 (15)
C27—Sb1—O3	89.15 (15)
C21—Sb1—O1	87.45 (16)
C15—Sb1—O1	87.74 (15)
C27—Sb1—O1	94.27 (15)
O3—Sb1—O1	174.49 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C32—H32⋯O2	0.93	2.39	3.105 (6)	134
C20—H20⋯O4	0.93	2.47	3.120 (6)	127
N1—H1B⋯N2ⁱ	0.865 (19)	2.43 (3)	3.211 (8)	150 (5)
N1—H1A⋯O2ⁱⁱ	0.86 (2)	2.43 (5)	3.114 (6)	137 (5)
N2—H2A⋯N1ⁱⁱⁱ	0.847 (19)	2.44 (2)	3.272 (7)	169 (5)
N2—H2B⋯O4^iv	0.847 (19)	2.36 (3)	3.151 (6)	156 (5)
C14—H14⋯O4^iv	0.93	2.58	3.369 (6)	143
C12—H12⋯O2^v	0.93	2.56	3.433 (6)	157
C23—H23⋯Cg1^vi	0.93	2.72	3.567 (7)	151
Symmetry codes: (i) $[x, -y+2, z+{\script{1\over 2}}]$ ; (ii) -x, -y+2, -z+1; (iii) $[-x, y-1, -z+{\script{1\over 2}}]$ ; (iv) $[-x, y, -z+{\script{1\over 2}}]$ ; (v) $[x, -y+1, z-{\script{1\over 2}}]$ ; (vi) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ . Cg1 is the centroid of the C27–C32 ring.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809043578/gk2233sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809043578/gk2233Isup2.hkl

checkCIF report

Comment top

Recently, the chemistry of antimony complexes derived from carboxylates has become an active area of research due to the biological perspective and their versatile bonding modes, the striking structural possibilities ranging from discrete monomeric structures to supramolecular assemblies (Yin et al. 2009). As a part of our ongoing investigations in ths field we have synthesized the title compound and determined its crystal structure. As is shown in Fig. 1, the central antimony atom is five-coordinated with a slightly distorted trigonal bipyramidal geometry. Around the central Sb1 atom, C15, C21 and C27 occupy the equatorial plane, while O1 and O3 lie in axial sites. The Sb—O bond distances (Sb1—O1 = 2.137 (3) Å; Sb1—O3 = 2.125 (3) Å) (Table 1) are comparable to those found in organoantimony arylhydroxmates (Wang et al. 2005). The Sb—C bond distances (Sb1—C15 = 2.108 (5) Å; Sb1—C21 = 2.098 (5) Å; Sb1—C27 = 2.109 (5) Å) of the compound lie within the normal range for Sb—C (phenyl) bonds (2.10–2.13 Å). The supramolecular structure of the title compound results from intermolecular C—H···O, N—H···O and N—H···N hydrogen-bonding interactions and C—H···Π stacking interactions (Fig. 2, Table 2) assembling the molecules into a three-dimensional supramolecular frameworks

Related literature top

For related structures, see: Yin et al. (2009); Wang et al. (2005).

Experimental top

The reaction was carried out under nitrogen atmosphere. 5-Amino-2-chlorobenzoic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to a stirred solution of methanol (30 ml) in a Schlenk flask and stirred for 0.5 h. Triphenylantimony dichloride (0.5 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at room temperature. The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of ether/n-hexane (1:1) to yield colourless blocks of the title compound (yield 80%). Anal. Calcd (%) for C₃₂H₂₅Cl₂N₂O₄Sb (Mr = 694.19): C, 55.37; H, 3.63; Cl, 10.21; N, 4.04. Found (%): C, 55.31; H, 3.76; Cl, 10.31; N, 4.15.

Structure description top

For related structures, see: Yin et al. (2009); Wang et al. (2005).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. View of the three-dimensional supramolecular network structure in the title compound.

Bis(5-amino-2-chlorobenzoato-κO)triphenylantimony(V) top

Crystal data top

[Sb(C₆H₅)₃(C₇H₅ClNO₂)₂]	F(000) = 2784
M_r = 694.19	D_x = 1.503 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3588 reflections
a = 30.683 (3) Å	θ = 2.4–23.7°
b = 9.0128 (12) Å	µ = 1.11 mm⁻¹
c = 23.096 (3) Å	T = 298 K
β = 106.161 (2)°	Block, colourless
V = 6134.6 (12) Å³	0.35 × 0.33 × 0.17 mm
Z = 8

Data collection top

Siemens SMART CCD area-detector diffractometer	5409 independent reflections
Radiation source: fine-focus sealed tube	3450 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
φ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→36
T_min = 0.697, T_max = 0.833	k = −10→10
15481 measured reflections	l = −27→22

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0252P)² + 12.9995P] where P = (F_o² + 2F_c²)/3
5409 reflections	(Δ/σ)_max < 0.001
386 parameters	Δρ_max = 0.86 e Å⁻³
4 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Sb(C₆H₅)₃(C₇H₅ClNO₂)₂]	V = 6134.6 (12) Å³
M_r = 694.19	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 30.683 (3) Å	µ = 1.11 mm⁻¹
b = 9.0128 (12) Å	T = 298 K
c = 23.096 (3) Å	0.35 × 0.33 × 0.17 mm
β = 106.161 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	5409 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3450 reflections with I > 2σ(I)
T_min = 0.697, T_max = 0.833	R_int = 0.046
15481 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	4 restraints
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0252P)² + 12.9995P] where P = (F_o² + 2F_c²)/3
5409 reflections	Δρ_max = 0.86 e Å⁻³
386 parameters	Δρ_min = −0.49 e Å⁻³

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

	x	y	z	U_iso*/U_eq
Sb1	0.133450 (10)	0.75719 (4)	0.387976 (14)	0.03529 (11)
Cl1	0.19341 (5)	0.92982 (17)	0.61118 (7)	0.0683 (4)
Cl2	0.17565 (5)	0.4095 (2)	0.25676 (8)	0.0998 (7)
N1	0.02031 (18)	1.2629 (6)	0.5343 (2)	0.0590 (12)
N2	−0.00974 (17)	0.4432 (6)	0.0918 (2)	0.0567 (13)
O1	0.14690 (11)	0.8704 (3)	0.47239 (14)	0.0427 (8)
O2	0.08342 (11)	0.7652 (4)	0.48081 (14)	0.0478 (8)
O3	0.12400 (10)	0.6602 (3)	0.30150 (13)	0.0411 (8)
O4	0.06817 (10)	0.5306 (4)	0.32076 (15)	0.0445 (9)
C1	0.11308 (17)	0.8607 (5)	0.4962 (2)	0.0390 (12)
C2	0.10837 (16)	0.9804 (5)	0.5384 (2)	0.0382 (12)
C3	0.14220 (16)	1.0253 (5)	0.5887 (2)	0.0432 (13)
C4	0.13472 (19)	1.1428 (6)	0.6237 (2)	0.0531 (14)
H4	0.1570	1.1696	0.6585	0.064*
C5	0.09432 (19)	1.2197 (6)	0.6068 (2)	0.0571 (15)
H5	0.0898	1.2997	0.6299	0.069*
C6	0.06032 (18)	1.1792 (6)	0.5558 (2)	0.0469 (13)
C7	0.06747 (17)	1.0588 (5)	0.5228 (2)	0.0426 (12)
H7	0.0445	1.0290	0.4893	0.051*
C8	0.09252 (16)	0.5591 (5)	0.2885 (2)	0.0360 (11)
C9	0.08637 (16)	0.4847 (5)	0.2287 (2)	0.0367 (11)
C10	0.12097 (16)	0.4236 (6)	0.2091 (2)	0.0524 (14)
C11	0.11202 (19)	0.3647 (6)	0.1518 (3)	0.0648 (17)
H11	0.1353	0.3213	0.1392	0.078*
C12	0.06878 (19)	0.3698 (6)	0.1131 (2)	0.0560 (15)
H12	0.0635	0.3331	0.0741	0.067*
C13	0.03327 (16)	0.4285 (5)	0.1315 (2)	0.0388 (12)
C14	0.04275 (16)	0.4845 (5)	0.1899 (2)	0.0391 (12)
H14	0.0191	0.5231	0.2032	0.047*
C15	0.07540 (17)	0.8918 (5)	0.3575 (2)	0.0408 (12)
C16	0.0831 (2)	1.0412 (6)	0.3515 (3)	0.0618 (16)
H16	0.1126	1.0768	0.3595	0.074*
C17	0.0468 (3)	1.1380 (7)	0.3337 (3)	0.084 (2)
H17	0.0518	1.2384	0.3286	0.100*
C18	0.0039 (3)	1.0854 (8)	0.3236 (3)	0.080 (2)
H18	−0.0203	1.1514	0.3129	0.095*
C19	−0.00454 (19)	0.9387 (7)	0.3289 (3)	0.0665 (17)
H19	−0.0342	0.9047	0.3212	0.080*
C20	0.03162 (18)	0.8400 (6)	0.3460 (2)	0.0526 (14)
H20	0.0262	0.7394	0.3497	0.063*
C21	0.18995 (16)	0.8670 (5)	0.3742 (2)	0.0413 (12)
C22	0.22768 (18)	0.8915 (6)	0.4213 (3)	0.0553 (15)
H22	0.2283	0.8595	0.4598	0.066*
C23	0.26495 (19)	0.9639 (7)	0.4118 (3)	0.0706 (18)
H23	0.2908	0.9784	0.4437	0.085*
C24	0.2638 (2)	1.0132 (8)	0.3563 (4)	0.085 (2)
H24	0.2887	1.0628	0.3503	0.102*
C25	0.2264 (2)	0.9912 (8)	0.3089 (3)	0.098 (3)
H25	0.2259	1.0255	0.2708	0.117*
C26	0.18914 (19)	0.9175 (7)	0.3177 (3)	0.0725 (19)
H26	0.1636	0.9022	0.2854	0.087*
C27	0.15298 (16)	0.5477 (5)	0.4274 (2)	0.0375 (12)
C28	0.18933 (18)	0.4839 (6)	0.4126 (2)	0.0545 (15)
H28	0.2048	0.5363	0.3898	0.065*
C29	0.2027 (2)	0.3410 (7)	0.4322 (3)	0.0680 (17)
H29	0.2274	0.2980	0.4228	0.082*
C30	0.1797 (2)	0.2636 (6)	0.4651 (3)	0.0632 (16)
H30	0.1886	0.1676	0.4779	0.076*
C31	0.14364 (19)	0.3273 (6)	0.4793 (3)	0.0584 (16)
H31	0.1280	0.2738	0.5015	0.070*
C32	0.12994 (16)	0.4711 (5)	0.4609 (2)	0.0447 (13)
H32	0.1056	0.5144	0.4713	0.054*
H1A	−0.0042 (13)	1.213 (6)	0.521 (3)	0.09 (3)*
H2A	−0.0141 (17)	0.386 (5)	0.0615 (16)	0.061 (19)*
H1B	0.0182 (19)	1.324 (5)	0.5623 (19)	0.08 (2)*
H2B	−0.0315 (12)	0.450 (6)	0.108 (2)	0.057 (19)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sb1	0.03935 (18)	0.03370 (18)	0.03511 (18)	−0.00248 (17)	0.01417 (13)	−0.00089 (18)
Cl1	0.0535 (9)	0.0761 (11)	0.0696 (11)	0.0103 (8)	0.0079 (7)	−0.0040 (8)
Cl2	0.0513 (10)	0.1624 (19)	0.0777 (13)	0.0366 (11)	0.0047 (8)	−0.0392 (12)
N1	0.059 (3)	0.057 (3)	0.064 (3)	0.010 (3)	0.023 (3)	0.000 (3)
N2	0.049 (3)	0.077 (4)	0.043 (3)	−0.002 (3)	0.010 (3)	−0.014 (3)
O1	0.047 (2)	0.047 (2)	0.038 (2)	0.0001 (16)	0.0193 (17)	−0.0075 (16)
O2	0.058 (2)	0.039 (2)	0.050 (2)	−0.0073 (18)	0.0201 (17)	−0.0049 (18)
O3	0.049 (2)	0.0379 (19)	0.038 (2)	−0.0100 (16)	0.0161 (16)	−0.0050 (16)
O4	0.042 (2)	0.055 (2)	0.040 (2)	−0.0035 (17)	0.0166 (17)	−0.0031 (17)
C1	0.050 (3)	0.031 (3)	0.038 (3)	0.003 (2)	0.014 (3)	0.001 (2)
C2	0.049 (3)	0.035 (3)	0.036 (3)	−0.005 (2)	0.021 (2)	0.001 (2)
C3	0.047 (3)	0.045 (3)	0.039 (3)	0.002 (2)	0.014 (3)	0.003 (2)
C4	0.063 (4)	0.055 (4)	0.041 (3)	−0.003 (3)	0.014 (3)	−0.007 (3)
C5	0.066 (4)	0.061 (4)	0.050 (4)	0.000 (3)	0.025 (3)	−0.013 (3)
C6	0.050 (3)	0.042 (3)	0.054 (4)	0.000 (3)	0.023 (3)	0.004 (3)
C7	0.054 (3)	0.040 (3)	0.034 (3)	−0.005 (2)	0.012 (2)	−0.001 (2)
C8	0.038 (3)	0.033 (3)	0.038 (3)	0.004 (2)	0.012 (2)	0.003 (2)
C9	0.039 (3)	0.036 (3)	0.039 (3)	0.000 (2)	0.018 (2)	0.001 (2)
C10	0.041 (3)	0.066 (4)	0.052 (4)	0.009 (3)	0.014 (3)	−0.012 (3)
C11	0.060 (4)	0.077 (4)	0.064 (4)	0.015 (3)	0.027 (3)	−0.027 (3)
C12	0.064 (4)	0.059 (4)	0.045 (4)	−0.003 (3)	0.016 (3)	−0.021 (3)
C13	0.046 (3)	0.037 (3)	0.037 (3)	−0.005 (2)	0.017 (3)	−0.006 (2)
C14	0.041 (3)	0.036 (3)	0.045 (3)	−0.002 (2)	0.019 (2)	−0.001 (2)
C15	0.050 (3)	0.040 (3)	0.034 (3)	0.002 (2)	0.014 (2)	0.000 (2)
C16	0.072 (4)	0.038 (3)	0.073 (5)	0.002 (3)	0.018 (3)	0.006 (3)
C17	0.118 (6)	0.037 (4)	0.092 (6)	0.025 (4)	0.024 (5)	0.005 (3)
C18	0.092 (5)	0.072 (5)	0.074 (5)	0.044 (4)	0.023 (4)	0.006 (4)
C19	0.056 (4)	0.070 (4)	0.077 (5)	0.019 (3)	0.023 (3)	0.008 (4)
C20	0.052 (4)	0.046 (3)	0.061 (4)	0.011 (3)	0.018 (3)	0.005 (3)
C21	0.045 (3)	0.037 (3)	0.047 (3)	−0.006 (2)	0.021 (3)	−0.006 (2)
C22	0.052 (4)	0.061 (4)	0.053 (4)	−0.010 (3)	0.013 (3)	−0.004 (3)
C23	0.045 (4)	0.085 (5)	0.078 (5)	−0.019 (3)	0.010 (3)	−0.020 (4)
C24	0.073 (5)	0.090 (5)	0.105 (6)	−0.037 (4)	0.044 (5)	−0.015 (5)
C25	0.099 (6)	0.126 (7)	0.080 (6)	−0.046 (5)	0.043 (5)	0.012 (5)
C26	0.063 (4)	0.101 (5)	0.057 (4)	−0.040 (4)	0.022 (3)	0.006 (4)
C27	0.042 (3)	0.033 (3)	0.034 (3)	0.002 (2)	0.004 (2)	0.001 (2)
C28	0.060 (4)	0.050 (3)	0.060 (4)	0.012 (3)	0.027 (3)	0.005 (3)
C29	0.066 (4)	0.064 (4)	0.073 (5)	0.027 (3)	0.018 (3)	0.003 (4)
C30	0.076 (4)	0.037 (3)	0.068 (4)	0.007 (3)	0.005 (3)	0.008 (3)
C31	0.057 (4)	0.044 (3)	0.070 (4)	−0.009 (3)	0.010 (3)	0.011 (3)
C32	0.044 (3)	0.041 (3)	0.049 (3)	−0.003 (2)	0.011 (3)	0.006 (3)

Geometric parameters (Å, º) top

Sb1—C21	2.098 (5)	C13—C14	1.392 (6)
Sb1—C15	2.108 (5)	C14—H14	0.9300
Sb1—C27	2.109 (5)	C15—C20	1.376 (6)
Sb1—O3	2.125 (3)	C15—C16	1.381 (6)
Sb1—O1	2.137 (3)	C16—C17	1.383 (7)
Cl1—C3	1.739 (5)	C16—H16	0.9300
Cl2—C10	1.736 (5)	C17—C18	1.357 (8)
N1—C6	1.408 (7)	C17—H17	0.9300
N1—H1A	0.86 (2)	C18—C19	1.360 (8)
N1—H1B	0.865 (19)	C18—H18	0.9300
N2—C13	1.388 (6)	C19—C20	1.391 (7)
N2—H2A	0.847 (19)	C19—H19	0.9300
N2—H2B	0.847 (19)	C20—H20	0.9300
O1—C1	1.305 (5)	C21—C22	1.369 (6)
O2—C1	1.231 (5)	C21—C26	1.375 (7)
O3—C8	1.301 (5)	C22—C23	1.386 (7)
O4—C8	1.220 (5)	C22—H22	0.9300
C1—C2	1.488 (6)	C23—C24	1.348 (8)
C2—C3	1.385 (6)	C23—H23	0.9300
C2—C7	1.397 (6)	C24—C25	1.361 (9)
C3—C4	1.390 (7)	C24—H24	0.9300
C4—C5	1.378 (7)	C25—C26	1.385 (7)
C4—H4	0.9300	C25—H25	0.9300
C5—C6	1.387 (7)	C26—H26	0.9300
C5—H5	0.9300	C27—C32	1.372 (6)
C6—C7	1.378 (6)	C27—C28	1.379 (6)
C7—H7	0.9300	C28—C29	1.388 (7)
C8—C9	1.499 (6)	C28—H28	0.9300
C9—C10	1.379 (6)	C29—C30	1.364 (8)
C9—C14	1.388 (6)	C29—H29	0.9300
C10—C11	1.381 (7)	C30—C31	1.366 (7)
C11—C12	1.378 (7)	C30—H30	0.9300
C11—H11	0.9300	C31—C32	1.391 (7)
C12—C13	1.380 (6)	C31—H31	0.9300
C12—H12	0.9300	C32—H32	0.9300

C21—Sb1—C15	109.59 (19)	C9—C14—C13	122.0 (5)
C21—Sb1—C27	109.92 (19)	C9—C14—H14	119.0
C15—Sb1—C27	140.49 (19)	C13—C14—H14	119.0
C21—Sb1—O3	87.33 (16)	C20—C15—C16	119.7 (5)
C15—Sb1—O3	92.36 (15)	C20—C15—Sb1	123.9 (4)
C27—Sb1—O3	89.15 (15)	C16—C15—Sb1	116.3 (4)
C21—Sb1—O1	87.45 (16)	C15—C16—C17	120.0 (6)
C15—Sb1—O1	87.74 (15)	C15—C16—H16	120.0
C27—Sb1—O1	94.27 (15)	C17—C16—H16	120.0
O3—Sb1—O1	174.49 (12)	C18—C17—C16	119.5 (6)
C6—N1—H1A	116 (4)	C18—C17—H17	120.3
C6—N1—H1B	108 (4)	C16—C17—H17	120.3
H1A—N1—H1B	112 (6)	C17—C18—C19	121.6 (6)
C13—N2—H2A	113 (4)	C17—C18—H18	119.2
C13—N2—H2B	116 (4)	C19—C18—H18	119.2
H2A—N2—H2B	116 (5)	C18—C19—C20	119.4 (6)
C1—O1—Sb1	112.2 (3)	C18—C19—H19	120.3
C8—O3—Sb1	113.8 (3)	C20—C19—H19	120.3
O2—C1—O1	122.4 (4)	C15—C20—C19	119.8 (5)
O2—C1—C2	119.8 (5)	C15—C20—H20	120.1
O1—C1—C2	117.5 (4)	C19—C20—H20	120.1
C3—C2—C7	118.5 (4)	C22—C21—C26	119.3 (5)
C3—C2—C1	125.1 (4)	C22—C21—Sb1	120.5 (4)
C7—C2—C1	116.2 (4)	C26—C21—Sb1	120.2 (4)
C2—C3—C4	120.3 (5)	C21—C22—C23	120.1 (5)
C2—C3—Cl1	120.6 (4)	C21—C22—H22	119.9
C4—C3—Cl1	119.0 (4)	C23—C22—H22	119.9
C5—C4—C3	119.9 (5)	C24—C23—C22	120.1 (6)
C5—C4—H4	120.0	C24—C23—H23	120.0
C3—C4—H4	120.0	C22—C23—H23	120.0
C4—C5—C6	120.9 (5)	C23—C24—C25	120.6 (6)
C4—C5—H5	119.6	C23—C24—H24	119.7
C6—C5—H5	119.6	C25—C24—H24	119.7
C7—C6—C5	118.6 (5)	C24—C25—C26	119.8 (7)
C7—C6—N1	118.9 (5)	C24—C25—H25	120.1
C5—C6—N1	122.3 (5)	C26—C25—H25	120.1
C6—C7—C2	121.7 (5)	C21—C26—C25	120.0 (6)
C6—C7—H7	119.1	C21—C26—H26	120.0
C2—C7—H7	119.1	C25—C26—H26	120.0
O4—C8—O3	123.2 (5)	C32—C27—C28	120.6 (5)
O4—C8—C9	121.8 (4)	C32—C27—Sb1	124.4 (4)
O3—C8—C9	114.9 (4)	C28—C27—Sb1	114.8 (4)
C10—C9—C14	118.6 (5)	C27—C28—C29	119.5 (5)
C10—C9—C8	124.7 (4)	C27—C28—H28	120.2
C14—C9—C8	116.6 (4)	C29—C28—H28	120.2
C9—C10—C11	120.1 (5)	C30—C29—C28	120.3 (6)
C9—C10—Cl2	121.1 (4)	C30—C29—H29	119.9
C11—C10—Cl2	118.6 (4)	C28—C29—H29	119.9
C12—C11—C10	120.5 (5)	C29—C30—C31	119.8 (5)
C12—C11—H11	119.8	C29—C30—H30	120.1
C10—C11—H11	119.8	C31—C30—H30	120.1
C11—C12—C13	120.9 (5)	C30—C31—C32	121.0 (6)
C11—C12—H12	119.6	C30—C31—H31	119.5
C13—C12—H12	119.6	C32—C31—H31	119.5
C12—C13—N2	121.3 (5)	C27—C32—C31	118.7 (5)
C12—C13—C14	117.8 (5)	C27—C32—H32	120.6
N2—C13—C14	120.6 (5)	C31—C32—H32	120.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32···O2	0.93	2.39	3.105 (6)	134
C20—H20···O4	0.93	2.47	3.120 (6)	127
N1—H1B···N2ⁱ	0.87 (2)	2.43 (3)	3.211 (8)	150 (5)
N1—H1A···O2ⁱⁱ	0.86 (2)	2.43 (5)	3.114 (6)	137 (5)
N2—H2A···N1ⁱⁱⁱ	0.85 (2)	2.44 (2)	3.272 (7)	169 (5)
N2—H2B···O4^iv	0.85 (2)	2.36 (3)	3.151 (6)	156 (5)
C14—H14···O4^iv	0.93	2.58	3.369 (6)	143
C12—H12···O2^v	0.93	2.56	3.433 (6)	157
C23—H23···Cg1^vi	0.93	2.72	3.567 (7)	151

Symmetry codes: (i) x, −y+2, z+1/2; (ii) −x, −y+2, −z+1; (iii) −x, y−1, −z+1/2; (iv) −x, y, −z+1/2; (v) x, −y+1, z−1/2; (vi) −x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Sb(C₆H₅)₃(C₇H₅ClNO₂)₂]
M_r	694.19
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	30.683 (3), 9.0128 (12), 23.096 (3)
β (°)	106.161 (2)
V (Å³)	6134.6 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.11
Crystal size (mm)	0.35 × 0.33 × 0.17

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.697, 0.833
No. of measured, independent and observed [I > 2σ(I)] reflections	15481, 5409, 3450
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.087, 1.04
No. of reflections	5409
No. of parameters	386
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0252P)² + 12.9995P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.49

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Sb1—C21	2.098 (5)	Sb1—O3	2.125 (3)
Sb1—C15	2.108 (5)	Sb1—O1	2.137 (3)
Sb1—C27	2.109 (5)

C21—Sb1—C15	109.59 (19)	C27—Sb1—O3	89.15 (15)
C21—Sb1—C27	109.92 (19)	C21—Sb1—O1	87.45 (16)
C15—Sb1—C27	140.49 (19)	C15—Sb1—O1	87.74 (15)
C21—Sb1—O3	87.33 (16)	C27—Sb1—O1	94.27 (15)
C15—Sb1—O3	92.36 (15)	O3—Sb1—O1	174.49 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32···O2	0.93	2.39	3.105 (6)	133.7
C20—H20···O4	0.93	2.47	3.120 (6)	126.7
N1—H1B···N2ⁱ	0.865 (19)	2.43 (3)	3.211 (8)	150 (5)
N1—H1A···O2ⁱⁱ	0.86 (2)	2.43 (5)	3.114 (6)	137 (5)
N2—H2A···N1ⁱⁱⁱ	0.847 (19)	2.44 (2)	3.272 (7)	169 (5)
N2—H2B···O4^iv	0.847 (19)	2.36 (3)	3.151 (6)	156 (5)
C14—H14···O4^iv	0.93	2.58	3.369 (6)	142.8
C12—H12···O2^v	0.93	2.56	3.433 (6)	157.0
C23—H23···Cg1^vi	0.93	2.72	3.567 (7)	151

Symmetry codes: (i) x, −y+2, z+1/2; (ii) −x, −y+2, −z+1; (iii) −x, y−1, −z+1/2; (iv) −x, y, −z+1/2; (v) x, −y+1, z−1/2; (vi) −x+1/2, −y+3/2, −z+1.

Acknowledgements

We acknowledge the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province (Y2008B48) for financial support.

References

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
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