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The asymmetric unit of the title complex, [Sb(C44H28N4)Cl2][Sb2Cl8]0.5·CH2Cl2, is composed of a SbV complex cation wherein the Sb atom is hexa­coordinated by four N atoms of the pyrrole rings of the tetra­phenyl­porphyrinate (TPP) ligands and two chloride ions, a half di-μ-chlorido-bis­[trichloridoanti­monate(III)] counter-anion and a dichloro­methane solvent mol­ecule. In the cation, the average Sb—N distance is 2.066 (2) Å, while the Sb—Cl distances are 2.3410 (11) and 2.3639 (12) Å. The central unit of the cation, SbN4C20, is far from being planar, with deviations of atoms from the least-squares plane ranging from −0.110 (4) to 0.124 (4) Å. The Sb—Cl distances in the anion, which is located about an inversion center, lie in the wide range 2.3715 (13)–2.7489 (13) Å, the longest distances being between the Sb and bridging Cl atoms. The crystal structure is stabilized by inter­molecular C—H...Cl inter­actions involving the cations, the anions and the solvent mol­ecules. The solvent mol­ecule is disordered over two orientations in a 0.901 (13):0.099 (13) ratio.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812018351/gk2479sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536812018351/gk2479Isup2.hkl
Contains datablock I

CCDC reference: 887144

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in solvent or counterion
  • R factor = 0.052
  • wR factor = 0.114
  • Data-to-parameter ratio = 24.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT074_ALERT_1_C Occupancy Parameter = 0.0 for .................. C45' PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. CL3 .. 2.99 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H31 .. CL6 .. 2.85 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H32 .. CL4 .. 2.90 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H32 .. CL7 .. 3.19 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C32 .. CL7 .. 4.08 Ang. PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 5 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 26 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 61 PLAT973_ALERT_2_C Large Calcd. Positive Residual Density on Sb1 1.28 eA-3 PLAT975_ALERT_2_C Positive Residual Density at 1.05A from N4 . 0.59 eA-3
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 3 PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large. 10.18 PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ................... 25 Perc. PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 11 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

In continuation of our research on the crystal structures of porphyrin complexes (Ben Moussa et al., 2011) we herein report the synthesis and crystal structure of the title compound.

The asymmetric unit of the title complex is presented in Fig. 1. The molecular dimensions in the cation of the title structure agree very well with the corresponding molecular dimensions reported for a closely related structure (Liu et al., 1996).

The crystal structure is stabilized by C—H···Cl intermolecular hydrogen bonding interactions involving the cations, anions and the solvate molecules (Table 1 & Fig. 2).

Related literature top

For related structures, see: Liu et al. (1996). Ben Moussa et al. (2011).

Experimental top

The reaction sequence leading to the formation of the title compound is not fully understood at present. SbCl5 (1–2 mL) was added to a solution of the porphyrin TPP (500 mg) in pyridine (25 mL) and the resulting solution was refluxed for 1 h. The pyridine and excess SbCl5 were removed under low pressure and the resulting purple solid was dissolved in CH2Cl2 (150 mL). An excess of dimethylglyoxime (80 g) was added in situ and the solution was refluxed for 3 h to yield the title compound. The crystal of the title compound were grown by diffusion of hexanes in a CH2Cl2 solution.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 and 0.99 Å, for aryl and methylene H-atoms, respectively. The Uiso(H) were allowed at 1.2Ueq(C). The solvate molecule, CH2Cl2, was disordered over two sites in a 0.901 (13):0.099 (13) ratio. EADP and EXYZ of SHELXL97 (Sheldrick, 2008) commands were used to model the disorder and C45—Cl distances for the smaller fraction were restrained at DFIX = 1.77 (1) Å.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius and the smaller fraction of the disordered CH2Cl2 has been excluded.
[Figure 2] Fig. 2. A view of the unit cell packing down the c-axis; H-atoms have been removed for clarity.
Dichlorido(5,10,15,20-tetraphenylporphyrinato-κ4N)antimony(V) hemi{di-µ-chlorido-bis[trichloridoantimonate(III)]} dichloromethane monosolvate top
Crystal data top
[Sb(C44H28N4)Cl2][Sb2Cl8]0.5·CH2Cl2Z = 2
Mr = 1153.83F(000) = 1132
Triclinic, P1Dx = 1.723 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.4488 (2) ÅCell parameters from 12653 reflections
b = 13.3868 (3) Åθ = 1.0–30.0°
c = 15.9828 (3) ŵ = 1.73 mm1
α = 68.3485 (10)°T = 173 K
β = 78.4895 (13)°Prism, purple
γ = 89.8390 (12)°0.16 × 0.14 × 0.11 mm
V = 2224.20 (8) Å3
Data collection top
Nonius KappaCCD
diffractometer
12918 independent reflections
Radiation source: fine-focus sealed tube10260 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ω and ϕ scansθmax = 30.0°, θmin = 2.4°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1616
Tmin = 0.769, Tmax = 0.832k = 1818
23249 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0155P)2 + 10.180P]
where P = (Fo2 + 2Fc2)/3
12918 reflections(Δ/σ)max < 0.001
539 parametersΔρmax = 1.36 e Å3
2 restraintsΔρmin = 0.88 e Å3
Crystal data top
[Sb(C44H28N4)Cl2][Sb2Cl8]0.5·CH2Cl2γ = 89.8390 (12)°
Mr = 1153.83V = 2224.20 (8) Å3
Triclinic, P1Z = 2
a = 11.4488 (2) ÅMo Kα radiation
b = 13.3868 (3) ŵ = 1.73 mm1
c = 15.9828 (3) ÅT = 173 K
α = 68.3485 (10)°0.16 × 0.14 × 0.11 mm
β = 78.4895 (13)°
Data collection top
Nonius KappaCCD
diffractometer
12918 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
10260 reflections with I > 2σ(I)
Tmin = 0.769, Tmax = 0.832Rint = 0.039
23249 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0522 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0155P)2 + 10.180P]
where P = (Fo2 + 2Fc2)/3
12918 reflectionsΔρmax = 1.36 e Å3
539 parametersΔρmin = 0.88 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
xyzUiso*/UeqOcc. (<1)
Sb10.19406 (2)0.81202 (2)0.391980 (18)0.02197 (6)
Cl10.39134 (10)0.85408 (9)0.30705 (8)0.0336 (2)
Cl20.00618 (10)0.76926 (10)0.47554 (8)0.0357 (2)
N10.2512 (3)0.7233 (3)0.5110 (2)0.0259 (7)
N20.2016 (3)0.9478 (3)0.4235 (2)0.0272 (7)
N30.1322 (3)0.9002 (3)0.2750 (2)0.0240 (7)
N40.1836 (3)0.6755 (3)0.3622 (2)0.0243 (7)
C10.2658 (4)0.6134 (3)0.5422 (3)0.0262 (8)
C20.3058 (4)0.5848 (4)0.6263 (3)0.0286 (9)
H20.32380.51480.66260.034*
C30.3138 (4)0.6747 (4)0.6458 (3)0.0287 (9)
H30.33710.67830.69850.034*
C40.2811 (4)0.7629 (3)0.5735 (3)0.0253 (8)
C50.2790 (4)0.8702 (3)0.5671 (3)0.0266 (8)
C60.2452 (4)0.9557 (3)0.4963 (3)0.0270 (8)
C70.2509 (4)1.0658 (4)0.4858 (3)0.0304 (9)
H70.27701.09400.52600.036*
C80.2125 (4)1.1233 (3)0.4082 (3)0.0296 (9)
H80.20791.19920.38430.036*
C90.1799 (4)1.0505 (3)0.3684 (3)0.0256 (8)
C100.1358 (4)1.0794 (3)0.2878 (3)0.0249 (8)
C110.1119 (4)1.0082 (3)0.2460 (3)0.0258 (8)
C120.0682 (4)1.0363 (4)0.1634 (3)0.0307 (9)
H120.04531.10530.12930.037*
C130.0652 (4)0.9476 (3)0.1418 (3)0.0298 (9)
H130.04000.94350.08990.036*
C140.1066 (4)0.8609 (3)0.2112 (3)0.0256 (8)
C150.1176 (4)0.7562 (3)0.2139 (3)0.0255 (8)
C160.1496 (4)0.6704 (3)0.2858 (3)0.0255 (8)
C170.1498 (4)0.5608 (3)0.2936 (3)0.0293 (9)
H170.12960.53400.25060.035*
C180.1835 (4)0.5014 (3)0.3726 (3)0.0287 (9)
H180.19090.42590.39480.034*
C190.2061 (4)0.5728 (3)0.4167 (3)0.0258 (8)
C200.2459 (4)0.5441 (3)0.4992 (3)0.0252 (8)
C210.3151 (4)0.8937 (3)0.6438 (3)0.0270 (8)
C220.4299 (4)0.8783 (4)0.6590 (4)0.0361 (10)
H220.48820.85850.61780.043*
C230.4598 (5)0.8918 (4)0.7342 (4)0.0440 (12)
H230.53820.87950.74500.053*
C240.3777 (5)0.9226 (4)0.7931 (4)0.0431 (12)
H240.39920.93230.84410.052*
C250.2630 (5)0.9394 (4)0.7781 (3)0.0379 (11)
H250.20580.96060.81900.046*
C260.2313 (4)0.9255 (4)0.7031 (3)0.0321 (9)
H260.15270.93770.69260.039*
C270.1143 (4)1.1961 (3)0.2426 (3)0.0261 (8)
C280.0235 (4)1.2411 (4)0.2842 (3)0.0314 (9)
H280.02651.19780.34150.038*
C290.0046 (5)1.3490 (4)0.2429 (4)0.0373 (10)
H290.05791.37980.27180.045*
C300.0776 (5)1.4120 (4)0.1590 (3)0.0357 (10)
H300.06381.48560.12990.043*
C310.1697 (5)1.3683 (4)0.1180 (3)0.0351 (10)
H310.22061.41220.06140.042*
C320.1887 (4)1.2595 (4)0.1592 (3)0.0306 (9)
H320.25191.22900.13060.037*
C330.0998 (4)0.7337 (3)0.1318 (3)0.0268 (8)
C340.0139 (5)0.7177 (4)0.1182 (3)0.0368 (10)
H340.08260.72090.16150.044*
C350.0268 (5)0.6970 (4)0.0412 (3)0.0398 (11)
H350.10440.68560.03210.048*
C360.0729 (5)0.6929 (4)0.0218 (3)0.0401 (11)
H360.06370.68080.07520.048*
C370.1852 (5)0.7062 (4)0.0079 (3)0.0393 (11)
H370.25340.70080.05060.047*
C380.1995 (4)0.7276 (4)0.0688 (3)0.0341 (10)
H380.27740.73800.07780.041*
C390.2740 (4)0.4298 (3)0.5425 (3)0.0265 (8)
C400.3759 (5)0.3939 (4)0.5034 (3)0.0389 (11)
H400.42600.44140.44790.047*
C410.4054 (5)0.2898 (4)0.5442 (4)0.0423 (12)
H410.47560.26610.51660.051*
C420.3337 (5)0.2193 (4)0.6252 (3)0.0350 (10)
H420.35510.14800.65380.042*
C430.2311 (5)0.2538 (4)0.6636 (3)0.0382 (11)
H430.18070.20560.71850.046*
C440.2004 (4)0.3587 (4)0.6226 (3)0.0360 (10)
H440.12910.38180.64950.043*
Sb20.45664 (3)0.49913 (3)0.13589 (2)0.03362 (8)
Cl30.40659 (12)0.35145 (11)0.29044 (9)0.0423 (3)
Cl40.51472 (12)0.65789 (11)0.03735 (9)0.0445 (3)
Cl50.46102 (15)0.63146 (12)0.20610 (10)0.0540 (4)
Cl60.66450 (11)0.48218 (12)0.12742 (8)0.0462 (3)
C450.6101 (7)0.8636 (5)0.0311 (4)0.0613 (17)
H45A0.53150.86390.07030.074*0.901 (13)
H45B0.61670.79090.02870.074*0.901 (13)
Cl70.6184 (2)0.9600 (3)0.08155 (17)0.0540 (7)0.901 (13)
Cl80.7249 (3)0.8909 (4)0.0805 (2)0.0829 (11)0.901 (13)
Cl7'0.622 (2)0.9865 (17)0.0659 (15)0.0540 (7)0.099 (13)
Cl8'0.7452 (17)0.850 (4)0.067 (2)0.0829 (11)0.099 (13)
C45'0.6101 (7)0.8636 (5)0.0311 (4)0.0613 (17)0.00
H45C0.54470.86440.08170.074*0.099 (13)
H45D0.59190.80210.01420.074*0.099 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sb10.02829 (13)0.01925 (12)0.01937 (12)0.00203 (9)0.00664 (10)0.00761 (9)
Cl10.0301 (5)0.0343 (6)0.0330 (5)0.0004 (4)0.0046 (4)0.0099 (4)
Cl20.0309 (5)0.0426 (6)0.0319 (5)0.0004 (5)0.0009 (4)0.0151 (5)
N10.0353 (19)0.0220 (17)0.0222 (16)0.0030 (14)0.0101 (14)0.0083 (13)
N20.0375 (19)0.0213 (17)0.0266 (17)0.0043 (14)0.0121 (15)0.0108 (14)
N30.0327 (18)0.0194 (16)0.0205 (15)0.0027 (13)0.0084 (14)0.0067 (13)
N40.0320 (18)0.0200 (16)0.0222 (16)0.0020 (13)0.0090 (14)0.0078 (13)
C10.031 (2)0.023 (2)0.0244 (19)0.0020 (16)0.0070 (16)0.0079 (16)
C20.037 (2)0.025 (2)0.0239 (19)0.0032 (17)0.0099 (17)0.0074 (16)
C30.035 (2)0.030 (2)0.0212 (19)0.0002 (17)0.0061 (17)0.0086 (16)
C40.029 (2)0.025 (2)0.0225 (18)0.0004 (16)0.0062 (16)0.0094 (16)
C50.027 (2)0.029 (2)0.0248 (19)0.0000 (16)0.0055 (16)0.0113 (17)
C60.034 (2)0.028 (2)0.0225 (19)0.0032 (17)0.0071 (17)0.0136 (16)
C70.038 (2)0.029 (2)0.030 (2)0.0048 (18)0.0111 (19)0.0167 (18)
C80.038 (2)0.020 (2)0.033 (2)0.0037 (17)0.0095 (19)0.0118 (17)
C90.033 (2)0.0184 (18)0.0237 (19)0.0029 (15)0.0036 (16)0.0076 (15)
C100.029 (2)0.0212 (19)0.0224 (18)0.0035 (15)0.0033 (16)0.0068 (15)
C110.034 (2)0.0215 (19)0.0228 (18)0.0043 (16)0.0084 (17)0.0084 (15)
C120.037 (2)0.028 (2)0.025 (2)0.0036 (18)0.0089 (18)0.0063 (17)
C130.039 (2)0.027 (2)0.025 (2)0.0018 (18)0.0130 (18)0.0084 (17)
C140.029 (2)0.025 (2)0.0214 (18)0.0004 (16)0.0064 (16)0.0076 (15)
C150.029 (2)0.027 (2)0.0243 (19)0.0015 (16)0.0072 (16)0.0132 (16)
C160.033 (2)0.024 (2)0.0200 (18)0.0016 (16)0.0053 (16)0.0087 (15)
C170.041 (2)0.022 (2)0.027 (2)0.0014 (17)0.0115 (18)0.0099 (16)
C180.039 (2)0.0203 (19)0.026 (2)0.0012 (17)0.0053 (18)0.0082 (16)
C190.031 (2)0.0196 (19)0.0235 (19)0.0011 (15)0.0035 (16)0.0054 (15)
C200.029 (2)0.024 (2)0.0221 (18)0.0016 (16)0.0073 (16)0.0077 (15)
C210.035 (2)0.023 (2)0.027 (2)0.0002 (16)0.0129 (17)0.0109 (16)
C220.033 (2)0.039 (3)0.044 (3)0.0003 (19)0.013 (2)0.021 (2)
C230.047 (3)0.044 (3)0.053 (3)0.005 (2)0.030 (3)0.022 (3)
C240.063 (3)0.032 (3)0.041 (3)0.005 (2)0.026 (3)0.013 (2)
C250.049 (3)0.035 (3)0.030 (2)0.005 (2)0.005 (2)0.015 (2)
C260.035 (2)0.036 (2)0.028 (2)0.0016 (19)0.0078 (18)0.0158 (19)
C270.032 (2)0.0190 (19)0.0258 (19)0.0003 (15)0.0065 (17)0.0065 (15)
C280.036 (2)0.028 (2)0.028 (2)0.0003 (18)0.0014 (18)0.0105 (17)
C290.044 (3)0.028 (2)0.045 (3)0.010 (2)0.011 (2)0.020 (2)
C300.053 (3)0.019 (2)0.039 (2)0.0020 (19)0.023 (2)0.0088 (18)
C310.046 (3)0.030 (2)0.025 (2)0.007 (2)0.009 (2)0.0048 (18)
C320.036 (2)0.028 (2)0.027 (2)0.0014 (18)0.0071 (18)0.0089 (17)
C330.040 (2)0.0217 (19)0.0215 (18)0.0044 (17)0.0109 (17)0.0094 (15)
C340.042 (3)0.041 (3)0.033 (2)0.008 (2)0.013 (2)0.018 (2)
C350.051 (3)0.040 (3)0.040 (3)0.008 (2)0.026 (2)0.019 (2)
C360.063 (3)0.033 (2)0.031 (2)0.005 (2)0.020 (2)0.014 (2)
C370.054 (3)0.037 (3)0.028 (2)0.003 (2)0.007 (2)0.015 (2)
C380.038 (2)0.038 (3)0.029 (2)0.002 (2)0.0072 (19)0.0160 (19)
C390.034 (2)0.023 (2)0.0237 (19)0.0024 (16)0.0058 (17)0.0091 (16)
C400.042 (3)0.026 (2)0.037 (2)0.0006 (19)0.004 (2)0.0041 (19)
C410.044 (3)0.030 (3)0.045 (3)0.011 (2)0.002 (2)0.010 (2)
C420.048 (3)0.019 (2)0.035 (2)0.0048 (19)0.014 (2)0.0049 (18)
C430.044 (3)0.025 (2)0.034 (2)0.0027 (19)0.003 (2)0.0007 (18)
C440.038 (2)0.027 (2)0.032 (2)0.0016 (19)0.0034 (19)0.0037 (18)
Sb20.03456 (16)0.03641 (17)0.02708 (15)0.00119 (13)0.00417 (12)0.00997 (12)
Cl30.0442 (7)0.0393 (7)0.0340 (6)0.0009 (5)0.0017 (5)0.0064 (5)
Cl40.0468 (7)0.0399 (7)0.0398 (6)0.0030 (5)0.0068 (5)0.0082 (5)
Cl50.0687 (9)0.0444 (8)0.0462 (7)0.0090 (7)0.0052 (7)0.0228 (6)
Cl60.0370 (6)0.0648 (9)0.0278 (5)0.0030 (6)0.0052 (5)0.0079 (6)
C450.077 (5)0.052 (4)0.050 (4)0.002 (3)0.020 (3)0.010 (3)
Cl70.0503 (8)0.0634 (13)0.0424 (9)0.0025 (9)0.0132 (7)0.0114 (9)
Cl80.0929 (16)0.108 (3)0.0576 (12)0.0136 (16)0.0360 (12)0.0319 (14)
Cl7'0.0503 (8)0.0634 (13)0.0424 (9)0.0025 (9)0.0132 (7)0.0114 (9)
Cl8'0.0929 (16)0.108 (3)0.0576 (12)0.0136 (16)0.0360 (12)0.0319 (14)
C45'0.077 (5)0.052 (4)0.050 (4)0.002 (3)0.020 (3)0.010 (3)
Geometric parameters (Å, º) top
Sb1—N42.061 (3)C22—H220.9500
Sb1—N22.063 (3)C23—C241.368 (8)
Sb1—N12.070 (3)C23—H230.9500
Sb1—N32.070 (3)C24—C251.384 (7)
Sb1—Cl12.3410 (11)C24—H240.9500
Sb1—Cl22.3639 (12)C25—C261.394 (6)
N1—C41.388 (5)C25—H250.9500
N1—C11.389 (5)C26—H260.9500
N2—C91.386 (5)C27—C281.380 (6)
N2—C61.392 (5)C27—C321.393 (6)
N3—C111.381 (5)C28—C291.386 (6)
N3—C141.384 (5)C28—H280.9500
N4—C161.378 (5)C29—C301.390 (7)
N4—C191.385 (5)C29—H290.9500
C1—C201.386 (6)C30—C311.374 (7)
C1—C21.424 (6)C30—H300.9500
C2—C31.358 (6)C31—C321.396 (6)
C2—H20.9500C31—H310.9500
C3—C41.425 (6)C32—H320.9500
C3—H30.9500C33—C381.387 (6)
C4—C51.402 (6)C33—C341.390 (6)
C5—C61.399 (6)C34—C351.392 (6)
C5—C211.503 (5)C34—H340.9500
C6—C71.420 (6)C35—C361.380 (8)
C7—C81.355 (6)C35—H350.9500
C7—H70.9500C36—C371.370 (7)
C8—C91.431 (6)C36—H360.9500
C8—H80.9500C37—C381.397 (6)
C9—C101.398 (6)C37—H370.9500
C10—C111.405 (6)C38—H380.9500
C10—C271.502 (5)C39—C401.382 (6)
C11—C121.426 (6)C39—C441.389 (6)
C12—C131.356 (6)C40—C411.377 (6)
C12—H120.9500C40—H400.9500
C13—C141.435 (6)C41—C421.385 (7)
C13—H130.9500C41—H410.9500
C14—C151.392 (6)C42—C431.374 (7)
C15—C161.402 (6)C42—H420.9500
C15—C331.502 (5)C43—C441.391 (6)
C16—C171.425 (6)C43—H430.9500
C17—C181.351 (6)C44—H440.9500
C17—H170.9500Sb2—Cl62.3715 (13)
C18—C191.431 (6)Sb2—Cl52.4267 (14)
C18—H180.9500Sb2—Cl32.4851 (13)
C19—C201.400 (5)Sb2—Cl42.7489 (13)
C20—C391.493 (6)C45—Cl81.765 (7)
C21—C221.384 (6)C45—Cl71.770 (7)
C21—C261.391 (6)C45—H45A0.9900
C22—C231.386 (7)C45—H45B0.9900
N4—Sb1—N2178.95 (15)C19—C20—C39117.0 (4)
N4—Sb1—N189.96 (13)C22—C21—C26119.5 (4)
N2—Sb1—N189.82 (13)C22—C21—C5120.4 (4)
N4—Sb1—N390.17 (13)C26—C21—C5120.0 (4)
N2—Sb1—N390.02 (13)C21—C22—C23120.1 (5)
N1—Sb1—N3178.45 (14)C21—C22—H22119.9
N4—Sb1—Cl190.38 (11)C23—C22—H22119.9
N2—Sb1—Cl190.66 (11)C24—C23—C22120.7 (5)
N1—Sb1—Cl191.30 (11)C24—C23—H23119.7
N3—Sb1—Cl190.24 (10)C22—C23—H23119.7
N4—Sb1—Cl289.01 (11)C23—C24—C25119.8 (4)
N2—Sb1—Cl289.95 (11)C23—C24—H24120.1
N1—Sb1—Cl289.48 (11)C25—C24—H24120.1
N3—Sb1—Cl288.98 (10)C24—C25—C26120.2 (5)
Cl1—Sb1—Cl2179.01 (4)C24—C25—H25119.9
C4—N1—C1108.2 (3)C26—C25—H25119.9
C4—N1—Sb1126.0 (3)C21—C26—C25119.7 (4)
C1—N1—Sb1125.8 (3)C21—C26—H26120.2
C9—N2—C6107.8 (3)C25—C26—H26120.2
C9—N2—Sb1125.4 (3)C28—C27—C32120.0 (4)
C6—N2—Sb1126.2 (3)C28—C27—C10120.5 (4)
C11—N3—C14108.3 (3)C32—C27—C10119.5 (4)
C11—N3—Sb1126.1 (3)C27—C28—C29120.4 (4)
C14—N3—Sb1125.5 (3)C27—C28—H28119.8
C16—N4—C19108.4 (3)C29—C28—H28119.8
C16—N4—Sb1125.7 (3)C28—C29—C30119.7 (5)
C19—N4—Sb1125.9 (3)C28—C29—H29120.1
C20—C1—N1126.3 (4)C30—C29—H29120.1
C20—C1—C2126.0 (4)C31—C30—C29120.2 (4)
N1—C1—C2107.6 (4)C31—C30—H30119.9
C3—C2—C1108.2 (4)C29—C30—H30119.9
C3—C2—H2125.9C30—C31—C32120.2 (4)
C1—C2—H2125.9C30—C31—H31119.9
C2—C3—C4108.3 (4)C32—C31—H31119.9
C2—C3—H3125.9C27—C32—C31119.4 (4)
C4—C3—H3125.9C27—C32—H32120.3
N1—C4—C5126.2 (4)C31—C32—H32120.3
N1—C4—C3107.6 (4)C38—C33—C34119.6 (4)
C5—C4—C3126.2 (4)C38—C33—C15118.9 (4)
C6—C5—C4125.5 (4)C34—C33—C15121.6 (4)
C6—C5—C21118.0 (4)C33—C34—C35119.9 (5)
C4—C5—C21116.5 (4)C33—C34—H34120.1
N2—C6—C5125.9 (4)C35—C34—H34120.1
N2—C6—C7108.3 (4)C36—C35—C34120.1 (5)
C5—C6—C7125.8 (4)C36—C35—H35119.9
C8—C7—C6107.9 (4)C34—C35—H35119.9
C8—C7—H7126.1C37—C36—C35120.4 (4)
C6—C7—H7126.1C37—C36—H36119.8
C7—C8—C9108.5 (4)C35—C36—H36119.8
C7—C8—H8125.8C36—C37—C38120.1 (5)
C9—C8—H8125.8C36—C37—H37119.9
N2—C9—C10126.9 (4)C38—C37—H37119.9
N2—C9—C8107.5 (4)C33—C38—C37119.9 (5)
C10—C9—C8125.6 (4)C33—C38—H38120.0
C9—C10—C11125.0 (4)C37—C38—H38120.0
C9—C10—C27116.8 (4)C40—C39—C44119.1 (4)
C11—C10—C27118.2 (4)C40—C39—C20119.7 (4)
N3—C11—C10126.1 (4)C44—C39—C20121.2 (4)
N3—C11—C12108.0 (4)C41—C40—C39120.5 (5)
C10—C11—C12125.8 (4)C41—C40—H40119.8
C13—C12—C11108.1 (4)C39—C40—H40119.8
C13—C12—H12125.9C40—C41—C42120.7 (5)
C11—C12—H12125.9C40—C41—H41119.7
C12—C13—C14108.0 (4)C42—C41—H41119.7
C12—C13—H13126.0C43—C42—C41119.1 (4)
C14—C13—H13126.0C43—C42—H42120.4
N3—C14—C15126.5 (4)C41—C42—H42120.4
N3—C14—C13107.6 (4)C42—C43—C44120.6 (4)
C15—C14—C13125.9 (4)C42—C43—H43119.7
C14—C15—C16125.2 (4)C44—C43—H43119.7
C14—C15—C33117.9 (4)C39—C44—C43120.0 (4)
C16—C15—C33116.8 (4)C39—C44—H44120.0
N4—C16—C15126.7 (4)C43—C44—H44120.0
N4—C16—C17107.6 (3)Cl6—Sb2—Cl590.73 (6)
C15—C16—C17125.7 (4)Cl6—Sb2—Cl391.77 (4)
C18—C17—C16108.6 (4)Cl5—Sb2—Cl390.67 (5)
C18—C17—H17125.7Cl6—Sb2—Cl487.52 (4)
C16—C17—H17125.7Cl5—Sb2—Cl490.98 (5)
C17—C18—C19107.7 (4)Cl3—Sb2—Cl4178.22 (5)
C17—C18—H18126.1Cl8—C45—Cl7111.5 (4)
C19—C18—H18126.1Cl8—C45—H45A109.3
N4—C19—C20126.2 (4)Cl7—C45—H45A109.3
N4—C19—C18107.7 (3)Cl8—C45—H45B109.3
C20—C19—C18126.1 (4)Cl7—C45—H45B109.3
C1—C20—C19125.7 (4)H45A—C45—H45B108.0
C1—C20—C39117.2 (4)
N4—Sb1—N1—C4179.0 (4)Sb1—N3—C14—C150.0 (6)
N2—Sb1—N1—C42.0 (4)C11—N3—C14—C131.9 (5)
Cl1—Sb1—N1—C488.6 (3)Sb1—N3—C14—C13179.4 (3)
Cl2—Sb1—N1—C492.0 (3)C12—C13—C14—N31.0 (5)
N4—Sb1—N1—C11.2 (4)C12—C13—C14—C15179.6 (4)
N2—Sb1—N1—C1177.8 (4)N3—C14—C15—C164.4 (7)
Cl1—Sb1—N1—C191.6 (3)C13—C14—C15—C16174.9 (4)
Cl2—Sb1—N1—C187.8 (3)N3—C14—C15—C33172.5 (4)
N1—Sb1—N2—C9176.1 (4)C13—C14—C15—C338.2 (7)
N3—Sb1—N2—C95.4 (4)C19—N4—C16—C15179.2 (4)
Cl1—Sb1—N2—C984.8 (4)Sb1—N4—C16—C150.9 (6)
Cl2—Sb1—N2—C994.4 (4)C19—N4—C16—C170.7 (5)
N1—Sb1—N2—C65.9 (4)Sb1—N4—C16—C17177.7 (3)
N3—Sb1—N2—C6175.7 (4)C14—C15—C16—N44.9 (7)
Cl1—Sb1—N2—C685.4 (4)C33—C15—C16—N4172.1 (4)
Cl2—Sb1—N2—C695.3 (4)C14—C15—C16—C17173.4 (4)
N4—Sb1—N3—C11178.9 (4)C33—C15—C16—C179.6 (7)
N2—Sb1—N3—C110.1 (4)N4—C16—C17—C180.3 (5)
Cl1—Sb1—N3—C1190.7 (3)C15—C16—C17—C18178.8 (4)
Cl2—Sb1—N3—C1189.9 (3)C16—C17—C18—C190.2 (5)
N4—Sb1—N3—C142.6 (4)C16—N4—C19—C20178.1 (4)
N2—Sb1—N3—C14178.5 (4)Sb1—N4—C19—C203.5 (6)
Cl1—Sb1—N3—C1487.8 (3)C16—N4—C19—C180.8 (5)
Cl2—Sb1—N3—C1491.6 (3)Sb1—N4—C19—C18177.5 (3)
N1—Sb1—N4—C16179.3 (4)C17—C18—C19—N40.6 (5)
N3—Sb1—N4—C162.2 (4)C17—C18—C19—C20178.3 (4)
Cl1—Sb1—N4—C1688.1 (3)N1—C1—C20—C190.7 (7)
Cl2—Sb1—N4—C1691.2 (3)C2—C1—C20—C19179.7 (4)
N1—Sb1—N4—C192.6 (4)N1—C1—C20—C39176.7 (4)
N3—Sb1—N4—C19175.9 (4)C2—C1—C20—C392.9 (7)
Cl1—Sb1—N4—C1993.9 (3)N4—C19—C20—C12.3 (7)
Cl2—Sb1—N4—C1986.9 (3)C18—C19—C20—C1179.0 (4)
C4—N1—C1—C20179.6 (4)N4—C19—C20—C39175.1 (4)
Sb1—N1—C1—C200.6 (6)C18—C19—C20—C393.6 (7)
C4—N1—C1—C20.0 (5)C6—C5—C21—C22117.5 (5)
Sb1—N1—C1—C2179.8 (3)C4—C5—C21—C2263.1 (6)
C20—C1—C2—C3179.7 (4)C6—C5—C21—C2666.0 (6)
N1—C1—C2—C30.7 (5)C4—C5—C21—C26113.3 (5)
C1—C2—C3—C41.1 (5)C26—C21—C22—C231.7 (7)
C1—N1—C4—C5179.6 (4)C5—C21—C22—C23174.8 (4)
Sb1—N1—C4—C50.5 (6)C21—C22—C23—C241.4 (8)
C1—N1—C4—C30.7 (5)C22—C23—C24—C250.6 (8)
Sb1—N1—C4—C3179.1 (3)C23—C24—C25—C260.2 (8)
C2—C3—C4—N11.1 (5)C22—C21—C26—C251.2 (7)
C2—C3—C4—C5179.2 (4)C5—C21—C26—C25175.3 (4)
N1—C4—C5—C60.5 (7)C24—C25—C26—C210.5 (7)
C3—C4—C5—C6179.1 (4)C9—C10—C27—C2869.0 (6)
N1—C4—C5—C21179.8 (4)C11—C10—C27—C28111.8 (5)
C3—C4—C5—C210.2 (6)C9—C10—C27—C32109.4 (5)
C9—N2—C6—C5179.4 (4)C11—C10—C27—C3269.7 (5)
Sb1—N2—C6—C57.8 (6)C32—C27—C28—C290.8 (7)
C9—N2—C6—C70.2 (5)C10—C27—C28—C29179.3 (4)
Sb1—N2—C6—C7171.5 (3)C27—C28—C29—C300.1 (7)
C4—C5—C6—N23.9 (7)C28—C29—C30—C311.4 (7)
C21—C5—C6—N2175.4 (4)C29—C30—C31—C321.6 (7)
C4—C5—C6—C7175.2 (4)C28—C27—C32—C310.6 (6)
C21—C5—C6—C75.5 (7)C10—C27—C32—C31179.1 (4)
N2—C6—C7—C80.4 (5)C30—C31—C32—C270.6 (7)
C5—C6—C7—C8178.9 (4)C14—C15—C33—C38100.7 (5)
C6—C7—C8—C90.8 (5)C16—C15—C33—C3876.4 (5)
C6—N2—C9—C10179.9 (4)C14—C15—C33—C3480.1 (6)
Sb1—N2—C9—C108.2 (6)C16—C15—C33—C34102.7 (5)
C6—N2—C9—C80.6 (5)C38—C33—C34—C350.8 (7)
Sb1—N2—C9—C8171.2 (3)C15—C33—C34—C35180.0 (4)
C7—C8—C9—N20.9 (5)C33—C34—C35—C360.3 (8)
C7—C8—C9—C10179.8 (4)C34—C35—C36—C371.8 (8)
N2—C9—C10—C113.8 (7)C35—C36—C37—C382.1 (8)
C8—C9—C10—C11175.4 (4)C34—C33—C38—C370.4 (7)
N2—C9—C10—C27177.1 (4)C15—C33—C38—C37179.6 (4)
C8—C9—C10—C273.7 (7)C36—C37—C38—C331.0 (7)
C14—N3—C11—C10174.9 (4)C1—C20—C39—C40104.7 (5)
Sb1—N3—C11—C103.8 (6)C19—C20—C39—C4072.9 (6)
C14—N3—C11—C122.1 (5)C1—C20—C39—C4474.1 (6)
Sb1—N3—C11—C12179.2 (3)C19—C20—C39—C44108.2 (5)
C9—C10—C11—N32.7 (7)C44—C39—C40—C411.2 (8)
C27—C10—C11—N3176.3 (4)C20—C39—C40—C41177.7 (5)
C9—C10—C11—C12179.2 (4)C39—C40—C41—C420.1 (8)
C27—C10—C11—C120.1 (7)C40—C41—C42—C431.3 (8)
N3—C11—C12—C131.4 (5)C41—C42—C43—C441.1 (8)
C10—C11—C12—C13175.5 (4)C40—C39—C44—C431.4 (7)
C11—C12—C13—C140.3 (5)C20—C39—C44—C43177.5 (4)
C11—N3—C14—C15178.7 (4)C42—C43—C44—C390.3 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Cl6i0.952.823.515 (4)131
C8—H8···Cl3ii0.952.833.455 (5)125
C3—H3···Cl3i0.952.993.528 (5)117
C45—H45B···Cl40.992.753.562 (7)140
C31—H31···Cl6iii0.952.853.775 (5)165
C32—H32···Cl4iii0.952.903.512 (5)123
C32—H32···Cl7iii0.953.194.076 (6)155
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z; (iii) x+1, y+2, z.

Experimental details

Crystal data
Chemical formula[Sb(C44H28N4)Cl2][Sb2Cl8]0.5·CH2Cl2
Mr1153.83
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)11.4488 (2), 13.3868 (3), 15.9828 (3)
α, β, γ (°)68.3485 (10), 78.4895 (13), 89.8390 (12)
V3)2224.20 (8)
Z2
Radiation typeMo Kα
µ (mm1)1.73
Crystal size (mm)0.16 × 0.14 × 0.11
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1997)
Tmin, Tmax0.769, 0.832
No. of measured, independent and
observed [I > 2σ(I)] reflections
23249, 12918, 10260
Rint0.039
(sin θ/λ)max1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.114, 1.11
No. of reflections12918
No. of parameters539
No. of restraints2
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0155P)2 + 10.180P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)1.36, 0.88

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Cl6i0.952.823.515 (4)131
C8—H8···Cl3ii0.952.833.455 (5)125
C45—H45B···Cl40.992.753.562 (7)140
C31—H31···Cl6iii0.952.853.775 (5)165
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z; (iii) x+1, y+2, z.
 

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