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metal-organic compounds
CRYSTALLOGRAPHIC COMMUNICATIONS |
ISSN: 2056-9890
Bis(5-amino-2-chlorobenzoato-κO)triphenylantimony(V)
Liyuan Wen,a Handong Yina* and Chuanhua Wanga
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
Experimental
Crystal data
[Sb(C6H5)3(C7H5ClNO2)2]
Mr = 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
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
Δρmax = 0.86 e Å−3
Δρmin = −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, °)
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.
Refinement top
The N-bound H atoms were located in a difference Fourier map. In the refinement process the N-H bond lengths were restrained to 0.85(2) Å and isotropic displacement parameters of these H atoms were freely refined. Other H atoms were positioned geometrically, with C—H = 0.93 Å and refined with a riding model; Uiso(H) = 1.2 Ueq (C).
Structure description 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
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. |
Crystal data
top
[Sb(C6H5)3(C7H5ClNO2)2] | F(000) = 2784 |
Mr = 694.19 | Dx = 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 | Rint = 0.046 |
φ and ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −25→36 |
Tmin = 0.697, Tmax = 0.833 | k = −10→10 |
15481 measured reflections | l = −27→22 |
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(Fo2) + (0.0252P)2 + 12.9995P] where P = (Fo2 + 2Fc2)/3 |
5409 reflections | (Δ/σ)max < 0.001 |
386 parameters | Δρmax = 0.86 e Å−3 |
4 restraints | Δρmin = −0.49 e Å−3 |
Crystal data
top
[Sb(C6H5)3(C7H5ClNO2)2] | V = 6134.6 (12) Å3 |
Mr = 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) |
Tmin = 0.697, Tmax = 0.833 | Rint = 0.046 |
15481 measured reflections |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
top
x | y | z | Uiso*/Ueq | ||
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)
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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) |
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 |
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···O4iv | 0.85 (2) | 2.36 (3) | 3.151 (6) | 156 (5) |
C14—H14···O4iv | 0.93 | 2.58 | 3.369 (6) | 143 |
C12—H12···O2v | 0.93 | 2.56 | 3.433 (6) | 157 |
C23—H23···Cg1vi | 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] |
Mr | 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) |
Tmin, Tmax | 0.697, 0.833 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15481, 5409, 3450 |
Rint | 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(Fo2) + (0.0252P)2 + 12.9995P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (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) |
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···O4iv | 0.847(19) | 2.36(3) | 3.151(6) | 156(5) |
C14—H14···O4iv | 0.93 | 2.58 | 3.369(6) | 142.8 |
C12—H12···O2v | 0.93 | 2.56 | 3.433(6) | 157.0 |
C23—H23···Cg1vi | 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
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. GoogleScholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. WebofScience CrossRef CAS IUCrJournals GoogleScholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. GoogleScholar
Wang, G. C., Lu, Y. N., Xiao, J., Yu, L., Song, H. B., Li, J. S., Cui, J. R., Wang, R. Q. & Ran, F. X. (2005). J. Organomet. Chem. 690, 151–156. WebofScience CSD CrossRef CAS GoogleScholar
Yin, H. D., Wen, L. Y., Cui, J. C. & Li, W. K. (2009). Polyhedron, 28, 2919–2926. WebofScience CSD CrossRef CAS GoogleScholar
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