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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): m1426.
Published online 2008 October 18. doi:  10.1107/S1600536808032844
PMCID: PMC2959708

Bis(4-amino­benzoato-κO)triphenylanti­mony(V)

Abstract

The structure of the title compound, [Sb(C6H5)3(C7H6NO2)2], contains two independent mol­ecules of similar configuration. The Sb atoms exhibit a distorted trigonal–bipyramidal geometry with the O atoms of two carboxyl­ate groups in the axial positions and the C atoms of the phenyl groups in the equatorial positions. In the crystal structure, mol­ecules are connected by inter­molecular N—H(...)O and N—H(...)N hydrogen-bonding inter­actions forming a chain structure along [100].

Related literature

For related structures, see: Wang et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1426-scheme1.jpg

Experimental

Crystal data

  • [Sb(C6H5)3(C7H6NO2)2]
  • M r = 625.31
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1426-efi1.jpg
  • a = 9.2831 (11) Å
  • b = 18.971 (2) Å
  • c = 16.3868 (19) Å
  • β = 95.543 (2)°
  • V = 2872.3 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.00 mm−1
  • T = 298 (2) K
  • 0.45 × 0.32 × 0.30 mm

Data collection

  • Siemens SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.662, T max = 0.754
  • 14481 measured reflections
  • 9132 independent reflections
  • 7713 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.099
  • S = 1.00
  • 9132 reflections
  • 703 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.62 e Å−3
  • Δρmin = −0.63 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3905 Friedel pairs
  • Flack parameter: −0.01 (2)

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032844/sg2267sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032844/sg2267Isup2.hkl

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

Acknowledgments

We acknowledge the National Natural Science Foundation of China (grant No. 20771053) and the Natural Science Foundation of Shandong Province (grant No. 2005ZX09) for financial support.

supplementary crystallographic information

Comment

The organoantimony(V) derivatives have attracted considerable attention due to the significant antimicrobial properties as well as antitumor activities recently. As a part of our ongoing investigations in ths field we have synthesized the title compound and determined its crystal structure. The crystal structure of the title compound which contains two independent molecules is shown in Fig.1 The Sb atom in both molecules assumes a distorted trigonal bipyramidal coordination geometry, provided by two carboxylate groups at the axial positions and three phenyl groups at the equatorial positions. The Sb—O bond distances (Sb1—O1 = 2.091 (4) Å; Sb1—O3 = 2.114 (4) Å; Sb2—O5 = 2.098 (5) Å; Sb2—O7 = 2.114 (5) Å) are comparable to those found in organoantimony arylhydroxmates (Wang et al. 2005). The Sb—C bond distances (Sb1—C15 = 2.121 (6) Å; Sb1—C21 = 2.115 (5) Å; Sb1—C27 = 2.115 (6) Å; Sb2—C47 = 2.101 (7) Å; Sb2—C53 = 2.074 (8) Å; Sb2—C59 = 2.068 (8) Å) of the compound lie within the normal range for Sb—C (phenyl) bonds (2.10–2.13 Å). In the crystal packing, molecules are linked by intermolecular N—H···O hydrogen bonds (Fig.2, Table 1,)

Experimental

The reaction was carried out under nitrogen atmosphere. 4- aminobenzoic acid (2 mmol) and sodium ethoxide (2.4 mmol) were added to a stirred solution of methanol (30 ml) in a Schlenk flask and stirred for 0.5 h. Triphenylantimony dichloride (1 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 dichloromethane/methanol (1:1) to yield colourless blocks (yield 86%. m.p.521 K). Anal. Calcd (%) for C32H27O4Sb1N2 (: C, 61.46; H, 4.35; O, 10.23; Sb, 19.47. Found (%): C, 61.40; H, 4.42; O, 10.28; Sb, 19.43

Refinement

The C—H and N—H hydrogen atoms were positioned with idealized geometry and were refined isotropic with Uiso(H) = 1.2 Ueq(C, O) for all H atoms using a riding model with N—H = 0.86 Å and C—H = 0.93 Å.

Figures

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 one-dimensional extended chain structure in the title compound. Intermolecular hydrogen bonds are shown as dashed lines. H atoms are omitted.

Crystal data

[Sb(C6H5)3(C7H6NO2)2]F(000) = 1264
Mr = 625.31Dx = 1.446 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.2831 (11) ÅCell parameters from 6029 reflections
b = 18.971 (2) Åθ = 2.4–25.0°
c = 16.3868 (19) ŵ = 1.00 mm1
β = 95.543 (2)°T = 298 K
V = 2872.3 (6) Å3Block, colourless
Z = 40.45 × 0.32 × 0.30 mm

Data collection

Siemens SMART CCD diffractometer9132 independent reflections
Radiation source: fine-focus sealed tube7713 reflections with I > 2σ(I)
graphiteRint = 0.024
[var phi] and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −6→11
Tmin = 0.662, Tmax = 0.754k = −22→21
14481 measured reflectionsl = −18→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.099w = 1/[σ2(Fo2) + (0.0504P)2 + 1.4161P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.020
9132 reflectionsΔρmax = 0.62 e Å3
703 parametersΔρmin = −0.63 e Å3
1 restraintAbsolute structure: Flack (1983), 3905 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.01 (2)

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

xyzUiso*/Ueq
Sb10.73466 (4)0.28424 (2)0.82632 (2)0.03634 (10)
Sb20.18571 (5)0.47931 (3)0.51514 (3)0.05668 (14)
N11.1819 (8)−0.0958 (4)0.8817 (5)0.087 (2)
H1A1.2195−0.11470.92650.104*
H1B1.1936−0.11510.83540.104*
N20.2686 (7)0.6590 (3)0.8782 (4)0.0706 (18)
H2A0.22830.67470.83240.085*
H2B0.25580.68040.92320.085*
N30.5218 (8)0.2962 (4)0.1067 (4)0.092 (2)
H3A0.52140.31390.05830.110*
H3B0.55420.25430.11630.110*
N4−0.2358 (11)0.6832 (6)0.8811 (6)0.140 (4)
H4A−0.26710.65410.91560.168*
H4B−0.24970.72770.88630.168*
O10.8572 (4)0.1920 (2)0.8234 (2)0.0440 (9)
O20.8288 (5)0.1826 (2)0.9549 (3)0.0526 (11)
O30.6149 (5)0.3792 (2)0.8218 (2)0.0443 (9)
O40.6343 (5)0.3790 (2)0.9567 (3)0.0493 (10)
O50.2755 (6)0.4204 (3)0.4243 (3)0.0726 (13)
O60.2597 (6)0.5165 (4)0.3472 (3)0.0797 (16)
O70.0979 (6)0.5259 (3)0.6166 (3)0.0702 (13)
O80.0856 (8)0.6313 (4)0.5604 (4)0.100 (2)
C10.8731 (6)0.1581 (3)0.8927 (4)0.0435 (14)
C20.9471 (6)0.0893 (3)0.8899 (3)0.0389 (13)
C30.9655 (7)0.0577 (3)0.8152 (4)0.0508 (15)
H30.92760.07910.76670.061*
C41.0389 (7)−0.0049 (4)0.8120 (4)0.0581 (17)
H41.0457−0.02720.76200.070*
C51.1035 (7)−0.0348 (4)0.8843 (4)0.0556 (16)
C61.0839 (7)−0.0032 (4)0.9585 (4)0.0564 (16)
H61.1245−0.02361.00700.068*
C71.0065 (7)0.0570 (3)0.9614 (4)0.0489 (14)
H70.99290.07701.01190.059*
C80.5971 (6)0.4081 (3)0.8911 (4)0.0433 (13)
C90.5226 (6)0.4774 (3)0.8866 (3)0.0396 (12)
C100.4583 (7)0.5036 (3)0.8128 (4)0.0516 (15)
H100.47090.47960.76450.062*
C110.3775 (7)0.5632 (4)0.8093 (4)0.0550 (16)
H110.33780.57980.75860.066*
C120.3531 (7)0.5999 (3)0.8797 (4)0.0500 (15)
C130.4238 (7)0.5761 (3)0.9538 (4)0.0493 (15)
H130.41590.60221.00120.059*
C140.5039 (7)0.5160 (3)0.9582 (4)0.0441 (14)
H140.54640.50031.00870.053*
C150.5510 (6)0.2234 (3)0.8487 (4)0.0387 (13)
C160.4431 (7)0.2462 (4)0.8938 (4)0.0486 (15)
H160.44760.29090.91720.058*
C170.3272 (7)0.2021 (4)0.9040 (4)0.0591 (17)
H170.25440.21710.93510.071*
C180.3189 (8)0.1375 (4)0.8694 (4)0.0593 (17)
H180.24080.10830.87710.071*
C190.4247 (8)0.1146 (4)0.8232 (5)0.0598 (17)
H190.41760.07020.79920.072*
C200.5409 (7)0.1568 (4)0.8123 (4)0.0503 (16)
H200.61270.14130.78070.060*
C210.7352 (6)0.2897 (4)0.6975 (3)0.0439 (12)
C220.6235 (10)0.3218 (5)0.6514 (5)0.074 (2)
H220.55050.34410.67660.089*
C230.6198 (11)0.3206 (5)0.5648 (5)0.089 (2)
H230.54300.34170.53320.106*
C240.7258 (10)0.2895 (6)0.5277 (4)0.079 (2)
H240.72340.28960.47080.095*
C250.8364 (10)0.2580 (4)0.5739 (5)0.077 (2)
H250.91060.23680.54850.092*
C260.8399 (9)0.2570 (4)0.6583 (4)0.0640 (19)
H260.91480.23370.68900.077*
C270.9160 (6)0.3383 (3)0.8840 (4)0.0478 (14)
C280.9866 (7)0.3211 (4)0.9585 (4)0.0661 (18)
H280.95090.28550.98990.079*
C291.1109 (8)0.3568 (4)0.9870 (5)0.076 (2)
H291.15970.34371.03690.091*
C301.1635 (8)0.4102 (4)0.9442 (5)0.075 (2)
H301.24700.43420.96420.090*
C311.0905 (8)0.4281 (5)0.8708 (5)0.083 (2)
H311.12570.46480.84070.100*
C320.9654 (8)0.3932 (4)0.8396 (4)0.0664 (18)
H320.91640.40680.78990.080*
C330.2923 (8)0.4546 (5)0.3556 (4)0.0627 (17)
C340.3543 (8)0.4121 (4)0.2917 (4)0.0572 (16)
C350.4020 (9)0.3444 (5)0.3069 (4)0.0703 (19)
H350.39430.32400.35780.084*
C360.4620 (9)0.3065 (5)0.2458 (5)0.077 (2)
H360.49670.26120.25710.092*
C370.4709 (9)0.3350 (5)0.1685 (4)0.0633 (19)
C380.4184 (8)0.4026 (5)0.1544 (4)0.0637 (18)
H380.42180.42250.10270.076*
C390.3612 (8)0.4412 (4)0.2145 (4)0.0650 (18)
H390.32740.48670.20350.078*
C400.0651 (9)0.5920 (5)0.6165 (5)0.0720 (18)
C41−0.0088 (9)0.6170 (4)0.6880 (5)0.0703 (19)
C42−0.0629 (9)0.5693 (5)0.7415 (5)0.080 (2)
H42−0.04770.52140.73350.097*
C43−0.1372 (10)0.5896 (5)0.8051 (5)0.086 (2)
H43−0.16960.55550.83980.104*
C44−0.1652 (12)0.6590 (6)0.8191 (6)0.095 (3)
C45−0.1070 (12)0.7097 (6)0.7685 (7)0.106 (3)
H45−0.11760.75750.77900.127*
C46−0.0299 (11)0.6869 (5)0.6996 (6)0.093 (2)
H460.00420.71980.66410.112*
C470.2041 (8)0.3860 (4)0.5844 (4)0.0598 (16)
C480.2146 (8)0.3879 (4)0.6682 (4)0.0654 (18)
H480.20990.43120.69450.079*
C490.2320 (10)0.3280 (5)0.7144 (5)0.079 (2)
H490.23590.33100.77120.095*
C500.2434 (10)0.2643 (5)0.6785 (6)0.087 (2)
H500.26430.22440.71060.104*
C510.2243 (12)0.2586 (5)0.5953 (6)0.096 (3)
H510.22180.21450.57050.115*
C520.2082 (10)0.3211 (5)0.5465 (5)0.079 (2)
H520.20050.31800.48960.095*
C530.3729 (8)0.5391 (4)0.5342 (5)0.0674 (18)
C540.4865 (9)0.5096 (5)0.5823 (6)0.102 (3)
H540.47870.46390.60190.122*
C550.6130 (12)0.5475 (6)0.6017 (8)0.126 (3)
H550.68630.52790.63730.151*
C560.6326 (12)0.6126 (6)0.5702 (7)0.122 (3)
H560.71920.63690.58200.147*
C570.5214 (11)0.6414 (6)0.5206 (8)0.131 (3)
H570.53070.68640.49920.158*
C580.3939 (10)0.6036 (5)0.5018 (7)0.104 (3)
H580.32100.62310.46590.125*
C59−0.0113 (9)0.4935 (5)0.4468 (5)0.083 (2)
C60−0.1083 (11)0.4402 (6)0.4473 (7)0.128 (3)
H60−0.08150.39770.47270.154*
C61−0.2491 (12)0.4491 (7)0.4096 (9)0.151 (4)
H61−0.31610.41290.41150.181*
C62−0.2886 (12)0.5100 (6)0.3702 (7)0.121 (3)
H62−0.38370.51640.34790.145*
C63−0.1893 (10)0.5617 (6)0.3636 (7)0.117 (3)
H63−0.21210.60180.33240.140*
C64−0.0543 (10)0.5531 (5)0.4043 (6)0.095 (3)
H640.01180.58980.40280.113*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sb10.03271 (18)0.03578 (18)0.04090 (19)−0.0036 (2)0.00541 (14)−0.00028 (19)
Sb20.0501 (3)0.0742 (3)0.0460 (2)0.0103 (2)0.0064 (2)0.0135 (2)
N10.092 (5)0.080 (5)0.087 (5)0.040 (4)0.004 (4)0.007 (4)
N20.080 (4)0.060 (4)0.073 (4)0.027 (4)0.013 (3)−0.006 (3)
N30.128 (6)0.080 (5)0.072 (4)−0.019 (5)0.040 (4)−0.015 (4)
N40.154 (8)0.151 (8)0.118 (7)0.053 (7)0.030 (6)−0.033 (6)
O10.035 (2)0.041 (2)0.056 (2)0.0056 (19)0.0067 (18)0.0095 (19)
O20.050 (3)0.053 (3)0.056 (3)−0.004 (2)0.008 (2)−0.002 (2)
O30.045 (2)0.038 (2)0.051 (2)0.0028 (19)0.0074 (19)−0.0051 (18)
O40.047 (2)0.043 (2)0.057 (3)−0.002 (2)0.000 (2)0.005 (2)
O50.078 (3)0.095 (3)0.048 (2)−0.001 (3)0.018 (2)0.005 (2)
O60.082 (4)0.097 (4)0.060 (3)0.027 (3)0.010 (3)0.010 (3)
O70.071 (3)0.073 (3)0.068 (3)0.020 (3)0.014 (2)0.013 (2)
O80.109 (5)0.103 (5)0.089 (4)0.017 (4)0.028 (4)0.035 (4)
C10.027 (3)0.049 (3)0.053 (3)−0.011 (3)0.001 (3)0.001 (3)
C20.031 (3)0.040 (3)0.044 (3)−0.004 (3)−0.003 (2)0.002 (3)
C30.050 (3)0.047 (3)0.054 (3)−0.001 (3)−0.003 (3)0.006 (3)
C40.062 (4)0.053 (4)0.058 (3)0.008 (3)0.001 (3)−0.004 (3)
C50.051 (3)0.053 (4)0.064 (4)0.010 (3)0.008 (3)0.011 (3)
C60.056 (4)0.059 (4)0.054 (3)0.010 (3)0.001 (3)0.019 (3)
C70.045 (3)0.053 (3)0.049 (3)0.000 (3)0.002 (3)0.008 (3)
C80.034 (3)0.039 (3)0.057 (3)−0.009 (3)0.004 (3)−0.005 (3)
C90.031 (3)0.039 (3)0.049 (3)−0.004 (3)0.002 (2)−0.006 (3)
C100.058 (4)0.052 (4)0.045 (3)0.006 (3)0.005 (3)−0.009 (3)
C110.056 (4)0.058 (4)0.049 (3)0.009 (3)−0.002 (3)0.000 (3)
C120.050 (3)0.046 (4)0.055 (4)0.002 (3)0.013 (3)0.000 (3)
C130.053 (3)0.044 (3)0.052 (3)−0.002 (3)0.011 (3)−0.013 (3)
C140.044 (3)0.040 (3)0.048 (3)−0.004 (3)0.005 (3)−0.003 (3)
C150.035 (3)0.036 (3)0.045 (3)−0.006 (3)0.000 (2)0.007 (2)
C160.044 (3)0.050 (3)0.053 (3)0.000 (3)0.006 (3)0.000 (3)
C170.043 (3)0.071 (4)0.066 (4)−0.008 (3)0.017 (3)0.011 (3)
C180.050 (4)0.052 (4)0.076 (4)−0.019 (3)0.003 (3)0.009 (3)
C190.050 (4)0.044 (4)0.082 (4)−0.018 (3)−0.006 (3)−0.003 (3)
C200.043 (3)0.049 (4)0.058 (3)−0.004 (3)0.000 (3)−0.004 (3)
C210.046 (3)0.049 (3)0.039 (3)−0.001 (3)0.011 (2)0.003 (3)
C220.080 (4)0.086 (5)0.059 (4)0.020 (4)0.015 (4)0.017 (4)
C230.099 (5)0.106 (6)0.060 (4)0.016 (5)−0.001 (4)0.017 (4)
C240.098 (5)0.092 (5)0.049 (4)−0.005 (5)0.022 (4)0.008 (4)
C250.084 (5)0.089 (5)0.061 (4)−0.001 (4)0.029 (4)−0.017 (4)
C260.068 (4)0.070 (4)0.054 (4)0.010 (4)0.009 (3)0.000 (3)
C270.031 (3)0.046 (3)0.066 (4)−0.007 (3)0.002 (3)−0.014 (3)
C280.059 (4)0.054 (4)0.083 (4)−0.013 (3)−0.009 (4)−0.009 (3)
C290.060 (4)0.065 (5)0.097 (5)−0.009 (4)−0.022 (4)−0.005 (4)
C300.039 (4)0.078 (5)0.107 (5)−0.012 (4)0.001 (4)−0.026 (4)
C310.079 (5)0.082 (5)0.093 (5)−0.048 (4)0.034 (4)−0.011 (4)
C320.061 (4)0.069 (4)0.069 (4)−0.028 (4)0.010 (3)−0.002 (3)
C330.052 (4)0.083 (4)0.053 (4)0.000 (4)0.005 (3)0.010 (3)
C340.055 (4)0.075 (4)0.043 (3)−0.006 (3)0.009 (3)0.001 (3)
C350.085 (4)0.084 (5)0.043 (3)−0.008 (4)0.013 (3)0.004 (3)
C360.082 (5)0.082 (5)0.069 (4)−0.005 (4)0.017 (4)0.003 (4)
C370.066 (4)0.078 (5)0.048 (4)−0.016 (4)0.013 (3)−0.005 (3)
C380.059 (4)0.092 (5)0.042 (3)−0.013 (4)0.013 (3)0.005 (3)
C390.049 (4)0.087 (5)0.059 (4)0.002 (3)0.005 (3)0.016 (3)
C400.063 (4)0.080 (4)0.074 (4)0.010 (4)0.009 (3)0.013 (4)
C410.068 (4)0.069 (4)0.073 (4)0.019 (4)0.002 (4)−0.004 (4)
C420.076 (4)0.091 (5)0.076 (4)0.013 (4)0.013 (4)0.001 (4)
C430.095 (5)0.097 (5)0.069 (4)0.016 (5)0.017 (4)−0.005 (4)
C440.098 (6)0.106 (6)0.081 (5)0.021 (5)0.008 (5)−0.016 (5)
C450.111 (6)0.096 (6)0.107 (6)0.027 (5)0.000 (5)−0.015 (5)
C460.098 (5)0.087 (5)0.093 (5)0.024 (5)0.002 (4)0.009 (4)
C470.059 (3)0.063 (4)0.059 (3)0.015 (3)0.012 (3)0.012 (3)
C480.076 (4)0.070 (4)0.051 (4)0.014 (4)0.007 (3)0.010 (3)
C490.082 (5)0.082 (5)0.074 (5)0.019 (4)0.010 (4)0.025 (4)
C500.097 (5)0.080 (6)0.085 (5)0.016 (4)0.016 (4)0.023 (4)
C510.111 (6)0.076 (5)0.102 (6)0.021 (5)0.013 (5)−0.007 (4)
C520.092 (5)0.080 (5)0.068 (4)0.006 (4)0.019 (4)0.002 (4)
C530.058 (4)0.075 (4)0.071 (4)0.011 (3)0.015 (3)0.014 (3)
C540.079 (5)0.109 (5)0.113 (5)−0.009 (5)−0.016 (5)0.023 (5)
C550.095 (6)0.136 (7)0.142 (7)−0.018 (6)−0.021 (6)0.026 (6)
C560.093 (6)0.125 (7)0.144 (7)−0.027 (6)−0.008 (6)0.007 (6)
C570.094 (6)0.114 (7)0.186 (8)−0.017 (6)0.011 (6)0.018 (7)
C580.072 (5)0.097 (5)0.140 (6)0.001 (5)−0.004 (5)0.020 (5)
C590.067 (4)0.110 (5)0.073 (4)−0.005 (4)0.009 (3)0.028 (4)
C600.108 (6)0.130 (6)0.138 (6)−0.024 (5)−0.031 (5)0.053 (5)
C610.101 (7)0.167 (8)0.178 (8)−0.022 (7)−0.016 (6)0.062 (7)
C620.084 (6)0.152 (8)0.122 (6)0.004 (6)−0.013 (5)0.042 (6)
C630.109 (6)0.126 (7)0.108 (6)0.026 (6)−0.021 (6)0.006 (6)
C640.088 (5)0.098 (5)0.090 (5)0.018 (5)−0.029 (4)0.004 (4)

Geometric parameters (Å, °)

Sb1—O12.091 (4)C24—H240.9300
Sb1—C212.115 (5)C25—C261.381 (10)
Sb1—O32.114 (4)C25—H250.9300
Sb1—C272.115 (6)C26—H260.9300
Sb1—C152.121 (6)C27—C321.375 (7)
Sb2—C592.068 (8)C27—C281.368 (7)
Sb2—O52.098 (5)C28—C291.379 (7)
Sb2—C472.101 (7)C28—H280.9300
Sb2—C532.074 (8)C29—C301.351 (8)
Sb2—O72.114 (5)C29—H290.9300
N1—C51.369 (9)C30—C311.364 (8)
N1—H1A0.8600C30—H300.9300
N1—H1B0.8600C31—C321.390 (7)
N2—C121.367 (8)C31—H310.9300
N2—H2A0.8600C32—H320.9300
N2—H2B0.8600C33—C341.481 (11)
N3—C371.373 (10)C34—C351.372 (11)
N3—H3A0.8600C34—C391.388 (9)
N3—H3B0.8600C35—C361.391 (11)
N4—C441.341 (12)C35—H350.9300
N4—H4A0.8600C36—C371.388 (10)
N4—H4B0.8600C36—H360.9300
O1—C11.300 (7)C37—C381.382 (11)
O2—C11.227 (7)C38—C391.375 (11)
O3—C81.287 (7)C38—H380.9300
O4—C81.228 (7)C39—H390.9300
O5—C331.320 (9)C40—C411.491 (11)
O6—C331.219 (9)C41—C461.357 (12)
O7—C401.290 (10)C41—C421.386 (12)
O8—C401.212 (9)C42—C431.360 (11)
C1—C21.478 (9)C42—H420.9300
C2—C31.389 (9)C43—C441.366 (14)
C2—C71.388 (8)C43—H430.9300
C3—C41.372 (9)C44—C451.411 (15)
C3—H30.9300C45—C461.459 (13)
C4—C51.395 (9)C45—H450.9300
C4—H40.9300C46—H460.9300
C5—C61.384 (9)C47—C481.367 (9)
C6—C71.352 (9)C47—C521.381 (11)
C6—H60.9300C48—C491.367 (11)
C7—H70.9300C48—H480.9300
C8—C91.483 (9)C49—C501.353 (13)
C9—C101.388 (8)C49—H490.9300
C9—C141.409 (8)C50—C511.362 (13)
C10—C111.356 (9)C50—H500.9300
C10—H100.9300C51—C521.430 (12)
C11—C121.385 (9)C51—H510.9300
C11—H110.9300C52—H520.9300
C12—C131.397 (9)C53—C581.354 (8)
C13—C141.360 (8)C53—C541.374 (8)
C13—H130.9300C54—C551.388 (8)
C14—H140.9300C54—H540.9300
C15—C161.370 (9)C55—C561.357 (9)
C15—C201.396 (9)C55—H550.9300
C16—C171.386 (9)C56—C571.365 (9)
C16—H160.9300C56—H560.9300
C17—C181.349 (10)C57—C581.393 (8)
C17—H170.9300C57—H570.9300
C18—C191.367 (10)C58—H580.9300
C18—H180.9300C59—C601.355 (8)
C19—C201.370 (9)C59—C641.367 (8)
C19—H190.9300C60—C611.401 (8)
C20—H200.9300C60—H600.9300
C21—C221.365 (10)C61—C621.357 (8)
C21—C261.364 (9)C61—H610.9300
C22—C231.416 (11)C62—C631.357 (9)
C22—H220.9300C62—H620.9300
C23—C241.342 (12)C63—C641.371 (8)
C23—H230.9300C63—H630.9300
C24—C251.354 (12)C64—H640.9300
O1—Sb1—C2188.0 (2)C32—C27—C28119.8 (6)
O1—Sb1—O3176.32 (17)C32—C27—Sb1115.0 (5)
C21—Sb1—O388.6 (2)C28—C27—Sb1125.2 (5)
O1—Sb1—C2790.3 (2)C27—C28—C29119.9 (7)
C21—Sb1—C27110.1 (2)C27—C28—H28120.1
O3—Sb1—C2789.8 (2)C29—C28—H28120.1
O1—Sb1—C1589.8 (2)C30—C29—C28121.7 (7)
C21—Sb1—C15106.2 (2)C30—C29—H29119.2
O3—Sb1—C1592.4 (2)C28—C29—H29119.2
C27—Sb1—C15143.6 (2)C29—C30—C31118.0 (7)
C59—Sb2—O594.4 (3)C29—C30—H30121.0
C59—Sb2—C47115.1 (3)C31—C30—H30121.0
O5—Sb2—C4785.3 (2)C30—C31—C32122.2 (7)
C59—Sb2—C53134.0 (3)C30—C31—H31118.9
O5—Sb2—C5390.8 (3)C32—C31—H31118.9
C47—Sb2—C53110.9 (3)C27—C32—C31118.4 (7)
C59—Sb2—O789.0 (3)C27—C32—H32120.8
O5—Sb2—O7172.1 (2)C31—C32—H32120.8
C47—Sb2—O786.9 (2)O6—C33—O5121.5 (7)
C53—Sb2—O791.9 (3)O6—C33—C34123.6 (7)
C5—N1—H1A120.0O5—C33—C34114.9 (8)
C5—N1—H1B120.0C35—C34—C39119.6 (7)
H1A—N1—H1B120.0C35—C34—C33121.5 (6)
C12—N2—H2A120.0C39—C34—C33118.9 (7)
C12—N2—H2B120.0C34—C35—C36119.9 (7)
H2A—N2—H2B120.0C34—C35—H35120.1
C37—N3—H3A120.0C36—C35—H35120.1
C37—N3—H3B120.0C37—C36—C35121.2 (8)
H3A—N3—H3B120.0C37—C36—H36119.4
C44—N4—H4A120.0C35—C36—H36119.4
C44—N4—H4B120.0N3—C37—C38121.0 (7)
H4A—N4—H4B120.0N3—C37—C36121.3 (8)
C1—O1—Sb1114.2 (4)C38—C37—C36117.6 (7)
C8—O3—Sb1116.4 (4)C37—C38—C39121.9 (7)
C33—O5—Sb2115.5 (5)C37—C38—H38119.1
C40—O7—Sb2121.0 (5)C39—C38—H38119.1
O2—C1—O1121.2 (6)C34—C39—C38119.7 (8)
O2—C1—C2123.7 (6)C34—C39—H39120.1
O1—C1—C2115.1 (5)C38—C39—H39120.1
C3—C2—C7118.8 (6)O8—C40—O7122.9 (8)
C3—C2—C1120.3 (5)O8—C40—C41121.2 (8)
C7—C2—C1120.8 (6)O7—C40—C41115.7 (7)
C4—C3—C2120.6 (6)C46—C41—C42118.9 (8)
C4—C3—H3119.7C46—C41—C40120.2 (8)
C2—C3—H3119.7C42—C41—C40120.8 (8)
C3—C4—C5119.7 (6)C43—C42—C41122.7 (9)
C3—C4—H4120.1C43—C42—H42118.6
C5—C4—H4120.1C41—C42—H42118.6
N1—C5—C6120.5 (6)C44—C43—C42121.4 (10)
N1—C5—C4120.3 (7)C44—C43—H43119.3
C6—C5—C4119.1 (6)C42—C43—H43119.3
C7—C6—C5120.8 (6)N4—C44—C43124.9 (11)
C7—C6—H6119.6N4—C44—C45117.1 (11)
C5—C6—H6119.6C43—C44—C45117.9 (10)
C6—C7—C2120.8 (6)C44—C45—C46119.8 (10)
C6—C7—H7119.6C44—C45—H45120.1
C2—C7—H7119.6C46—C45—H45120.1
O4—C8—O3122.1 (6)C41—C46—C45119.1 (10)
O4—C8—C9122.2 (6)C41—C46—H46120.4
O3—C8—C9115.7 (6)C45—C46—H46120.4
C10—C9—C14117.5 (6)C48—C47—C52118.3 (7)
C10—C9—C8121.3 (5)C48—C47—Sb2120.9 (6)
C14—C9—C8120.9 (5)C52—C47—Sb2120.8 (6)
C11—C10—C9121.7 (6)C47—C48—C49121.8 (8)
C11—C10—H10119.1C47—C48—H48119.1
C9—C10—H10119.1C49—C48—H48119.1
C10—C11—C12121.2 (6)C50—C49—C48120.8 (8)
C10—C11—H11119.4C50—C49—H49119.6
C12—C11—H11119.4C48—C49—H49119.6
N2—C12—C11122.4 (6)C49—C50—C51119.8 (8)
N2—C12—C13120.0 (6)C49—C50—H50120.1
C11—C12—C13117.5 (6)C51—C50—H50120.1
C14—C13—C12121.7 (6)C50—C51—C52119.4 (8)
C14—C13—H13119.2C50—C51—H51120.3
C12—C13—H13119.2C52—C51—H51120.3
C13—C14—C9120.2 (6)C47—C52—C51119.5 (8)
C13—C14—H14119.9C47—C52—H52120.2
C9—C14—H14119.9C51—C52—H52120.2
C16—C15—C20119.6 (6)C58—C53—C54117.5 (8)
C16—C15—Sb1124.3 (5)C58—C53—Sb2125.8 (6)
C20—C15—Sb1116.1 (5)C54—C53—Sb2116.7 (6)
C17—C16—C15119.4 (6)C53—C54—C55120.4 (9)
C17—C16—H16120.3C53—C54—H54119.8
C15—C16—H16120.3C55—C54—H54119.8
C18—C17—C16120.7 (7)C56—C55—C54121.7 (11)
C18—C17—H17119.6C56—C55—H55119.1
C16—C17—H17119.6C54—C55—H55119.1
C17—C18—C19120.4 (6)C55—C56—C57118.0 (11)
C17—C18—H18119.8C55—C56—H56121.0
C19—C18—H18119.8C57—C56—H56121.0
C20—C19—C18120.3 (7)C56—C57—C58120.2 (11)
C20—C19—H19119.9C56—C57—H57119.9
C18—C19—H19119.9C58—C57—H57119.9
C19—C20—C15119.6 (7)C53—C58—C57122.0 (10)
C19—C20—H20120.2C53—C58—H58119.0
C15—C20—H20120.2C57—C58—H58119.0
C22—C21—C26118.7 (6)C60—C59—C64117.3 (9)
C22—C21—Sb1119.9 (5)C60—C59—Sb2117.0 (6)
C26—C21—Sb1121.2 (5)C64—C59—Sb2125.7 (7)
C21—C22—C23119.4 (8)C59—C60—C61120.0 (10)
C21—C22—H22120.3C59—C60—H60120.0
C23—C22—H22120.3C61—C60—H60120.0
C24—C23—C22120.8 (8)C62—C61—C60120.7 (11)
C24—C23—H23119.6C62—C61—H61119.6
C22—C23—H23119.6C60—C61—H61119.6
C23—C24—C25119.3 (7)C61—C62—C63119.9 (11)
C23—C24—H24120.3C61—C62—H62120.1
C25—C24—H24120.3C63—C62—H62120.1
C24—C25—C26120.6 (8)C62—C63—C64118.1 (11)
C24—C25—H25119.7C62—C63—H63120.9
C26—C25—H25119.7C64—C63—H63120.9
C25—C26—C21121.1 (7)C59—C64—C63123.7 (10)
C25—C26—H26119.5C59—C64—H64118.2
C21—C26—H26119.5C63—C64—H64118.2
C21—Sb1—O1—C1−170.7 (4)C32—C27—C28—C29−3.1 (11)
O3—Sb1—O1—C1170 (2)Sb1—C27—C28—C29174.8 (6)
C27—Sb1—O1—C179.2 (4)C27—C28—C29—C302.1 (13)
C15—Sb1—O1—C1−64.4 (4)C28—C29—C30—C31−0.5 (13)
O1—Sb1—O3—C8−152 (3)C29—C30—C31—C320.1 (13)
C21—Sb1—O3—C8−171.1 (4)C28—C27—C32—C312.6 (11)
C27—Sb1—O3—C8−60.9 (4)Sb1—C27—C32—C31−175.4 (6)
C15—Sb1—O3—C882.7 (4)C30—C31—C32—C27−1.1 (13)
C59—Sb2—O5—C3364.5 (5)Sb2—O5—C33—O61.3 (10)
C47—Sb2—O5—C33179.3 (5)Sb2—O5—C33—C34−179.4 (5)
C53—Sb2—O5—C33−69.8 (5)O6—C33—C34—C35173.7 (8)
O7—Sb2—O5—C33−179.9 (15)O5—C33—C34—C35−5.6 (11)
C59—Sb2—O7—C40−68.5 (6)O6—C33—C34—C39−7.6 (11)
O5—Sb2—O7—C40175.6 (14)O5—C33—C34—C39173.1 (6)
C47—Sb2—O7—C40176.4 (6)C39—C34—C35—C362.4 (12)
C53—Sb2—O7—C4065.5 (6)C33—C34—C35—C36−178.9 (7)
Sb1—O1—C1—O2−5.7 (7)C34—C35—C36—C37−1.9 (13)
Sb1—O1—C1—C2174.4 (4)C35—C36—C37—N3−176.0 (8)
O2—C1—C2—C3165.7 (6)C35—C36—C37—C380.2 (12)
O1—C1—C2—C3−14.3 (8)N3—C37—C38—C39177.2 (7)
O2—C1—C2—C7−17.9 (9)C36—C37—C38—C391.0 (12)
O1—C1—C2—C7162.0 (5)C35—C34—C39—C38−1.3 (11)
C7—C2—C3—C41.0 (9)C33—C34—C39—C38−180.0 (7)
C1—C2—C3—C4177.5 (6)C37—C38—C39—C34−0.5 (11)
C2—C3—C4—C5−4.0 (10)Sb2—O7—C40—O8−2.0 (11)
C3—C4—C5—N1−177.4 (7)Sb2—O7—C40—C41174.4 (5)
C3—C4—C5—C64.3 (10)O8—C40—C41—C46−12.7 (13)
N1—C5—C6—C7−180.0 (7)O7—C40—C41—C46170.9 (8)
C4—C5—C6—C7−1.7 (11)O8—C40—C41—C42164.4 (9)
C5—C6—C7—C2−1.3 (10)O7—C40—C41—C42−12.0 (12)
C3—C2—C7—C61.6 (9)C46—C41—C42—C430.4 (14)
C1—C2—C7—C6−174.8 (6)C40—C41—C42—C43−176.7 (8)
Sb1—O3—C8—O4−7.2 (7)C41—C42—C43—C441.1 (15)
Sb1—O3—C8—C9175.6 (4)C42—C43—C44—N4−179.0 (10)
O4—C8—C9—C10−168.2 (6)C42—C43—C44—C45−3.8 (15)
O3—C8—C9—C109.0 (8)N4—C44—C45—C46−179.5 (9)
O4—C8—C9—C146.3 (9)C43—C44—C45—C464.9 (15)
O3—C8—C9—C14−176.5 (5)C42—C41—C46—C450.8 (14)
C14—C9—C10—C11−1.4 (10)C40—C41—C46—C45177.9 (8)
C8—C9—C10—C11173.2 (6)C44—C45—C46—C41−3.5 (15)
C9—C10—C11—C12−1.4 (11)C59—Sb2—C47—C48−112.4 (7)
C10—C11—C12—N2−178.0 (7)O5—Sb2—C47—C48155.0 (6)
C10—C11—C12—C134.8 (10)C53—Sb2—C47—C4865.9 (7)
N2—C12—C13—C14177.2 (6)O7—Sb2—C47—C48−24.9 (6)
C11—C12—C13—C14−5.5 (10)C59—Sb2—C47—C5268.6 (7)
C12—C13—C14—C92.7 (9)O5—Sb2—C47—C52−24.0 (7)
C10—C9—C14—C130.8 (9)C53—Sb2—C47—C52−113.0 (7)
C8—C9—C14—C13−173.9 (5)O7—Sb2—C47—C52156.1 (7)
O1—Sb1—C15—C16148.7 (5)C52—C47—C48—C491.4 (13)
C21—Sb1—C15—C16−123.5 (5)Sb2—C47—C48—C49−177.6 (7)
O3—Sb1—C15—C16−34.3 (5)C47—C48—C49—C501.9 (14)
C27—Sb1—C15—C1658.5 (7)C48—C49—C50—C51−6.1 (16)
O1—Sb1—C15—C20−33.2 (5)C49—C50—C51—C526.9 (16)
C21—Sb1—C15—C2054.6 (5)C48—C47—C52—C51−0.5 (13)
O3—Sb1—C15—C20143.8 (5)Sb2—C47—C52—C51178.5 (7)
C27—Sb1—C15—C20−123.4 (5)C50—C51—C52—C47−3.6 (15)
C20—C15—C16—C171.5 (9)C59—Sb2—C53—C581.1 (11)
Sb1—C15—C16—C17179.5 (5)O5—Sb2—C53—C5898.0 (9)
C15—C16—C17—C18−0.8 (10)C47—Sb2—C53—C58−176.8 (8)
C16—C17—C18—C19−0.3 (11)O7—Sb2—C53—C58−89.4 (9)
C17—C18—C19—C200.6 (11)C59—Sb2—C53—C54−177.0 (7)
C18—C19—C20—C150.1 (11)O5—Sb2—C53—C54−80.2 (7)
C16—C15—C20—C19−1.2 (10)C47—Sb2—C53—C545.0 (8)
Sb1—C15—C20—C19−179.4 (5)O7—Sb2—C53—C5492.4 (7)
O1—Sb1—C21—C22151.9 (7)C58—C53—C54—C555.2 (16)
O3—Sb1—C21—C22−29.3 (7)Sb2—C53—C54—C55−176.5 (9)
C27—Sb1—C21—C22−118.6 (6)C53—C54—C55—C56−4(2)
C15—Sb1—C21—C2262.7 (7)C54—C55—C56—C572(2)
O1—Sb1—C21—C26−23.0 (6)C55—C56—C57—C58−2(2)
O3—Sb1—C21—C26155.8 (6)C54—C53—C58—C57−4.6 (16)
C27—Sb1—C21—C2666.5 (6)Sb2—C53—C58—C57177.3 (9)
C15—Sb1—C21—C26−112.2 (6)C56—C57—C58—C533(2)
C26—C21—C22—C23−0.4 (12)O5—Sb2—C59—C6082.4 (9)
Sb1—C21—C22—C23−175.5 (7)C47—Sb2—C59—C60−4.4 (10)
C21—C22—C23—C24−1.1 (15)C53—Sb2—C59—C60177.7 (8)
C22—C23—C24—C251.0 (15)O7—Sb2—C59—C60−90.5 (9)
C23—C24—C25—C260.7 (14)O5—Sb2—C59—C64−100.7 (9)
C24—C25—C26—C21−2.3 (13)C47—Sb2—C59—C64172.5 (8)
C22—C21—C26—C252.1 (12)C53—Sb2—C59—C64−5.4 (11)
Sb1—C21—C26—C25177.1 (6)O7—Sb2—C59—C6486.4 (9)
O1—Sb1—C27—C32117.0 (5)C64—C59—C60—C61−3.9 (19)
C21—Sb1—C27—C3229.0 (6)Sb2—C59—C60—C61173.3 (11)
O3—Sb1—C27—C32−59.4 (5)C59—C60—C61—C622(2)
C15—Sb1—C27—C32−153.0 (5)C60—C61—C62—C633(2)
O1—Sb1—C27—C28−61.0 (6)C61—C62—C63—C64−6(2)
C21—Sb1—C27—C28−148.9 (6)C60—C59—C64—C630.9 (17)
O3—Sb1—C27—C28122.7 (6)Sb2—C59—C64—C63−176.0 (8)
C15—Sb1—C27—C2829.0 (8)C62—C63—C64—C594.3 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3B···N2i0.862.443.245 (11)156
N3—H3A···O4ii0.862.403.178 (8)151
N2—H2B···O2iii0.862.222.996 (8)151
N1—H1A···O4iv0.862.243.046 (8)156

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2267).

References

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  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • 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.

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