Tris(3-methyl­anilinium) penta­chlorido­anti­monate(III) chloride

Liu, M.-L.

doi:10.1107/S1600536811049087

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1812

https://doi.org/10.1107/S1600536811049087

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Tris(3-methylanilinium) pentachloridoantimonate(III) chloride

Ming-Liang Liu ^a ^*

^aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: jgsdxlml@163.com

(Received 16 November 2011; accepted 17 November 2011; online 23 November 2011)

In the title compound, (C₇H₁₀N)₃[SbCl₅]Cl, the Sb^III cation is coordinated by five Cl⁻ anions in a distorted square-pyramidal geometry, in which the longest Sb—Cl distance of 3.0319 (14) Å indicates a weak coordination bond. In the crystal, the 3-methylanilinium cations link with the complex antimonate anions and Cl⁻ anions via N—H⋯Cl hydrogen bonds.

Related literature

For background to the title compound, see: Fu et al. (2011 ); Zhang et al. (2010 ). For related structures, see: Chen (2009a ,b ); Vijjulatha et al. (1997 ); Wei et al. (2008 ); Zhai et al. (2007 ).

Experimental

Crystal data

(C₇H₁₀N)₃[SbCl₅]Cl
M_r = 658.93
Monoclinic, P 2₁ /c
a = 17.171 (3) Å
b = 9.4065 (19) Å
c = 20.958 (8) Å
β = 122.36 (2)°
V = 2859.4 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.54 mm⁻¹
T = 293 K
0.36 × 0.32 × 0.28 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.566, T_max = 0.640
23714 measured reflections
5029 independent reflections
3776 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.085
S = 1.07
5029 reflections
286 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Table 1
Selected bond lengths (Å)

Sb1—Cl2	3.0319 (14)
Sb1—Cl3	2.5325 (14)
Sb1—Cl4	2.4182 (15)
Sb1—Cl5	2.4043 (13)
Sb1—Cl6	2.7779 (14)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯Cl1	0.89	2.72	3.602 (4)	169
N1—H1E⋯Cl6ⁱ	0.89	2.67	3.513 (4)	158
N1—H1F⋯Cl2ⁱⁱ	0.89	2.59	3.455 (4)	163
N2—H2A⋯Cl1	0.89	2.37	3.240 (4)	166
N2—H2B⋯Cl1ⁱⁱⁱ	0.89	2.40	3.249 (4)	160
N2—H2C⋯Cl2^iv	0.89	2.41	3.238 (4)	155
N3—H3A⋯Cl1^v	0.89	2.47	3.344 (5)	167
N3—H3B⋯Cl2ⁱⁱⁱ	0.89	2.56	3.366 (5)	151
N3—H3C⋯Cl1ⁱⁱⁱ	0.89	2.55	3.355 (5)	151
Symmetry codes: (i) x, y-1, z; (ii) -x+2, -y+1, -z+1; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) x, y+1, z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811049087/xu5391sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049087/xu5391Isup2.hkl

checkCIF report

Comment top

Recently much attention has been devoted to crystals containing organic ions and inorganic ions due to the tunebility of their special structural features and their potential ferroelectrics property (Fu et al., 2011; Zhang et al., 2010). In our laboratory, the title compound has been synthesized and its crystal structure is herein reported.

The title compound, [(C₇H₁₀N)₃SbCl₅]⁺.Cl^-, has an asymmetric unit that consists of three C₇H₁₀N cations, one antimony(III) pentachloride anion and one chloride anion all in general positions (Fig 1). The non-hydrgen atoms of C₇H₁₀N cation are nearly coplanar, the antimony(III) atom is coordinated by five chlorine atoms, forming a distorted square-pyramid, the Sb—Cl bond distances range from 2.4043 (13) to 3.0319 (14) Å (Table 1). This range of values is compared to those observed in dimorpholinium pentachloridoantimonate(III) (2.045 (8)–2.92230 (9) Å; Chen et al., 2009a) and that reported for diisonicotinium pentachloridoantimonate(III) monohydrate (2.3642 (12) to 2.9002 (14) Å; Chen et al., 2009b). The existence of N—H···Cl hydrogen-bonding interactions gives rise a three-dimensional structure (Fig. 2).

Related literature top

For background to the title compound, see: Fu et al. (2011); Zhang et al. (2010). For related structures, see: Chen (2009a,b); Vijjulatha et al. (1997); Wei et al. (2008); Zhai et al. (2007).

Experimental top

3.21 g (0.03 mol) of 3-methylbenzenamine was firstly dissolved in 30 ml ethanol, to which 1.1 g (0.03 mol) of hydrochloric acid was then added to afford the solution, then the 2.28 g (0.01 mol) antimony chloride was dissolved in 20 ml ethanol which was added hydrochloric acid, at last, mixed the above solution without any precipitation under stirring at the ambient temperature. Single crystals suitable for X-ray structure analysis were obtained by the slow evaporation of the above solution after 4 days in air.

The dielectric constant of the compound as a function of temperature indicates that the permittivity is basically temperature-independent (ε = C/(T–T₀)), suggesting that this compound is not ferroelectric or there may be no distinct phase transition occurring within the measured temperature within the measured temperature (below the melting point).

Structure description top

For background to the title compound, see: Fu et al. (2011); Zhang et al. (2010). For related structures, see: Chen (2009a,b); Vijjulatha et al. (1997); Wei et al. (2008); Zhai et al. (2007).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 title compound, showing the atomic numbering scheme with 30% probability displacement ellipsoids.
	Fig. 2. Crystal structure of the title compound with view along the b axis. Intermolecular interactions are shown as dashed lines.

Tris(3-methylanilinium) pentachloridoantimonate(III) chloride top

Crystal data top

(C₇H₁₀N)₃[SbCl₅]Cl	F(000) = 1320
M_r = 658.93	D_x = 1.531 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5029 reflections
a = 17.171 (3) Å	θ = 3.1–27.6°
b = 9.4065 (19) Å	µ = 1.54 mm⁻¹
c = 20.958 (8) Å	T = 293 K
β = 122.36 (2)°	Block, colorless
V = 2859.4 (13) Å³	0.36 × 0.32 × 0.28 mm
Z = 4

Data collection top

Rigaku SCXmini diffractometer	5029 independent reflections
Radiation source: fine-focus sealed tube	3776 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
CCD_Profile_fitting scans	θ_max = 25.0°, θ_min = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −20→20
T_min = 0.566, T_max = 0.640	k = −11→11
23714 measured reflections	l = −24→24

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0238P)² + 3.2828P] where P = (F_o² + 2F_c²)/3
5029 reflections	(Δ/σ)_max = 0.001
286 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

(C₇H₁₀N)₃[SbCl₅]Cl	V = 2859.4 (13) Å³
M_r = 658.93	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.171 (3) Å	µ = 1.54 mm⁻¹
b = 9.4065 (19) Å	T = 293 K
c = 20.958 (8) Å	0.36 × 0.32 × 0.28 mm
β = 122.36 (2)°

Data collection top

Rigaku SCXmini diffractometer	5029 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3776 reflections with I > 2σ(I)
T_min = 0.566, T_max = 0.640	R_int = 0.061
23714 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.07	Δρ_max = 0.45 e Å⁻³
5029 reflections	Δρ_min = −0.57 e Å⁻³
286 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.5562 (4)	0.3197 (7)	0.3106 (4)	0.109 (2)
H1A	0.5571	0.4166	0.2967	0.164*
H1B	0.5821	0.3142	0.3640	0.164*
H1C	0.4937	0.2861	0.2842	0.164*
C6	0.7590 (3)	0.1338 (5)	0.3223 (3)	0.0463 (11)
N1	0.8598 (2)	0.1246 (4)	0.3760 (2)	0.0598 (11)
H1D	0.8881	0.1332	0.3510	0.090*
H1E	0.8739	0.0409	0.3994	0.090*
H1F	0.8781	0.1941	0.4099	0.090*
C3	0.5726 (3)	0.1547 (5)	0.2232 (3)	0.0597 (14)
H3	0.5093	0.1608	0.1890	0.072*
C7	0.7080 (3)	0.2161 (5)	0.3400 (3)	0.0564 (13)
H7	0.7370	0.2646	0.3858	0.068*
C5	0.7193 (3)	0.0606 (5)	0.2556 (3)	0.0544 (13)
H5	0.7547	0.0049	0.2439	0.065*
C2	0.6120 (3)	0.2288 (5)	0.2900 (3)	0.0574 (14)
C4	0.6246 (4)	0.0718 (6)	0.2059 (3)	0.0645 (15)
H4	0.5961	0.0225	0.1604	0.077*
C15	0.6589 (5)	0.6670 (8)	0.1612 (4)	0.109 (2)
H15A	0.5931	0.6597	0.1358	0.163*
H15B	0.6833	0.7087	0.2101	0.163*
H15C	0.6848	0.5740	0.1668	0.163*
N3	0.8982 (3)	0.8778 (5)	0.1259 (3)	0.0741 (13)
H3A	0.9256	0.9322	0.1670	0.111*
H3B	0.9028	0.9188	0.0898	0.111*
H3C	0.9254	0.7931	0.1368	0.111*
C18	0.7989 (4)	0.8600 (6)	0.0991 (3)	0.0604 (14)
C16	0.6829 (4)	0.7576 (6)	0.1162 (3)	0.0653 (16)
C17	0.7770 (4)	0.7709 (6)	0.1383 (3)	0.0669 (15)
H17	0.8228	0.7192	0.1791	0.080*
C19	0.7337 (4)	0.9369 (6)	0.0383 (3)	0.0748 (17)
H19	0.7509	0.9967	0.0126	0.090*
C20	0.6404 (5)	0.9249 (7)	0.0149 (4)	0.091 (2)
H20	0.5948	0.9753	−0.0265	0.109*
C21	0.6195 (4)	0.8376 (7)	0.0548 (4)	0.0789 (18)
H21	0.5579	0.8309	0.0398	0.095*
C8	0.6102 (4)	0.5583 (6)	−0.0837 (3)	0.092 (2)
H8A	0.5445	0.5476	−0.1093	0.139*
H8B	0.6301	0.5295	−0.1166	0.139*
H8C	0.6265	0.6560	−0.0696	0.139*
C13	0.7928 (3)	0.3667 (5)	0.0939 (3)	0.0463 (11)
N2	0.8939 (2)	0.3478 (4)	0.1373 (2)	0.0596 (11)
H2A	0.9108	0.2925	0.1771	0.089*
H2B	0.9212	0.4321	0.1529	0.089*
H2C	0.9107	0.3073	0.1080	0.089*
C10	0.6068 (4)	0.3990 (6)	0.0117 (4)	0.0782 (17)
H10	0.5429	0.4085	−0.0154	0.094*
C12	0.7431 (4)	0.3015 (6)	0.1186 (3)	0.0657 (15)
H12	0.7718	0.2477	0.1626	0.079*
C9	0.6563 (4)	0.4669 (5)	−0.0139 (3)	0.0589 (14)
C14	0.7512 (4)	0.4478 (5)	0.0293 (3)	0.0538 (13)
H14	0.7875	0.4909	0.0141	0.065*
C11	0.6489 (4)	0.3181 (7)	0.0760 (4)	0.0848 (19)
H11	0.6131	0.2734	0.0911	0.102*
Sb1	0.89514 (2)	0.62601 (3)	0.415711 (17)	0.04348 (11)
Cl3	0.88469 (9)	0.44094 (13)	0.32367 (8)	0.0642 (4)
Cl4	0.72983 (9)	0.63871 (17)	0.35705 (8)	0.0752 (4)
Cl5	0.89748 (9)	0.80416 (12)	0.33449 (7)	0.0545 (3)
Cl6	0.91678 (9)	0.85259 (14)	0.50888 (7)	0.0625 (4)
Cl1	0.96680 (9)	0.10773 (12)	0.26801 (7)	0.0559 (3)
Cl2	1.10143 (8)	0.63935 (13)	0.48357 (7)	0.0537 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.082 (5)	0.112 (6)	0.139 (7)	0.027 (4)	0.063 (5)	−0.020 (5)
C6	0.035 (2)	0.035 (2)	0.057 (3)	0.002 (2)	0.017 (2)	0.006 (2)
N1	0.046 (2)	0.044 (2)	0.070 (3)	−0.002 (2)	0.019 (2)	−0.007 (2)
C3	0.042 (3)	0.054 (3)	0.068 (4)	0.002 (3)	0.019 (3)	0.013 (3)
C7	0.052 (3)	0.050 (3)	0.058 (3)	−0.004 (2)	0.023 (3)	−0.016 (3)
C5	0.054 (3)	0.048 (3)	0.056 (3)	0.008 (2)	0.026 (3)	−0.006 (3)
C2	0.048 (3)	0.049 (3)	0.081 (4)	0.006 (2)	0.038 (3)	0.002 (3)
C4	0.056 (4)	0.064 (3)	0.051 (3)	0.002 (3)	0.014 (3)	−0.009 (3)
C15	0.105 (6)	0.131 (7)	0.092 (5)	−0.017 (5)	0.054 (5)	0.001 (5)
N3	0.060 (3)	0.077 (3)	0.091 (3)	−0.003 (3)	0.044 (3)	−0.005 (3)
C18	0.059 (3)	0.063 (3)	0.074 (4)	−0.014 (3)	0.045 (3)	−0.023 (3)
C16	0.077 (4)	0.073 (4)	0.067 (4)	−0.029 (3)	0.053 (4)	−0.028 (3)
C17	0.075 (4)	0.068 (4)	0.064 (4)	−0.005 (3)	0.041 (3)	−0.023 (3)
C19	0.061 (4)	0.076 (4)	0.089 (5)	−0.003 (3)	0.041 (4)	0.000 (4)
C20	0.073 (5)	0.098 (5)	0.105 (5)	−0.008 (4)	0.050 (4)	0.005 (4)
C21	0.057 (4)	0.099 (5)	0.077 (5)	−0.013 (4)	0.033 (4)	−0.025 (4)
C8	0.100 (5)	0.077 (4)	0.083 (5)	0.019 (4)	0.036 (4)	0.017 (4)
C13	0.039 (3)	0.039 (3)	0.054 (3)	−0.006 (2)	0.021 (2)	−0.011 (2)
N2	0.049 (3)	0.052 (3)	0.071 (3)	−0.004 (2)	0.028 (2)	−0.009 (2)
C10	0.048 (3)	0.083 (4)	0.086 (5)	0.006 (3)	0.025 (3)	0.005 (4)
C12	0.065 (4)	0.072 (4)	0.061 (4)	−0.003 (3)	0.034 (3)	0.011 (3)
C9	0.063 (4)	0.045 (3)	0.058 (3)	0.006 (3)	0.025 (3)	0.001 (3)
C14	0.062 (4)	0.040 (3)	0.065 (4)	−0.010 (2)	0.038 (3)	−0.003 (3)
C11	0.056 (4)	0.106 (5)	0.107 (5)	−0.003 (3)	0.054 (4)	0.025 (4)
Sb1	0.04486 (19)	0.03558 (17)	0.0501 (2)	0.00541 (15)	0.02546 (15)	0.00729 (15)
Cl3	0.0684 (9)	0.0456 (7)	0.0781 (10)	−0.0013 (6)	0.0388 (8)	−0.0083 (7)
Cl4	0.0484 (8)	0.0886 (11)	0.0848 (10)	0.0051 (8)	0.0331 (8)	0.0039 (9)
Cl5	0.0633 (8)	0.0436 (7)	0.0570 (8)	0.0114 (6)	0.0325 (7)	0.0160 (6)
Cl6	0.0567 (8)	0.0648 (9)	0.0676 (9)	0.0076 (7)	0.0343 (7)	−0.0057 (7)
Cl1	0.0608 (8)	0.0441 (7)	0.0609 (8)	0.0055 (6)	0.0312 (7)	0.0050 (6)
Cl2	0.0490 (7)	0.0505 (7)	0.0526 (7)	0.0027 (6)	0.0212 (6)	0.0055 (6)

Geometric parameters (Å, º) top

C1—C2	1.510 (7)	C17—H17	0.9300
C1—H1A	0.9600	C19—C20	1.406 (8)
C1—H1B	0.9600	C19—H19	0.9300
C1—H1C	0.9600	C20—C21	1.350 (8)
C6—C7	1.360 (6)	C20—H20	0.9300
C6—C5	1.369 (6)	C21—H21	0.9300
C6—N1	1.478 (5)	C8—C9	1.504 (7)
N1—H1D	0.8900	C8—H8A	0.9600
N1—H1E	0.8900	C8—H8B	0.9600
N1—H1F	0.8900	C8—H8C	0.9600
C3—C4	1.373 (7)	C13—C12	1.357 (6)
C3—C2	1.375 (7)	C13—C14	1.375 (6)
C3—H3	0.9300	C13—N2	1.478 (5)
C7—C2	1.408 (7)	N2—H2A	0.8900
C7—H7	0.9300	N2—H2B	0.8900
C5—C4	1.388 (6)	N2—H2C	0.8900
C5—H5	0.9300	C10—C11	1.368 (8)
C4—H4	0.9300	C10—C9	1.382 (7)
C15—C16	1.484 (8)	C10—H10	0.9300
C15—H15A	0.9600	C12—C11	1.376 (7)
C15—H15B	0.9600	C12—H12	0.9300
C15—H15C	0.9600	C9—C14	1.390 (7)
N3—C18	1.492 (6)	C14—H14	0.9300
N3—H3A	0.8900	C11—H11	0.9300
N3—H3B	0.8900	Sb1—Cl2	3.0319 (14)
N3—H3C	0.8900	Sb1—Cl3	2.5325 (14)
C18—C17	1.360 (7)	Sb1—Cl4	2.4182 (15)
C18—C19	1.369 (7)	Sb1—Cl5	2.4043 (13)
C16—C21	1.381 (8)	Sb1—Cl6	2.7779 (14)
C16—C17	1.428 (7)

C2—C1—H1A	109.5	C16—C17—H17	120.4
C2—C1—H1B	109.5	C18—C19—C20	119.6 (6)
H1A—C1—H1B	109.5	C18—C19—H19	120.2
C2—C1—H1C	109.5	C20—C19—H19	120.2
H1A—C1—H1C	109.5	C21—C20—C19	117.6 (6)
H1B—C1—H1C	109.5	C21—C20—H20	121.2
C7—C6—C5	121.5 (4)	C19—C20—H20	121.2
C7—C6—N1	119.3 (4)	C20—C21—C16	124.7 (6)
C5—C6—N1	119.2 (4)	C20—C21—H21	117.6
C6—N1—H1D	109.5	C16—C21—H21	117.6
C6—N1—H1E	109.5	C9—C8—H8A	109.5
H1D—N1—H1E	109.5	C9—C8—H8B	109.5
C6—N1—H1F	109.5	H8A—C8—H8B	109.5
H1D—N1—H1F	109.5	C9—C8—H8C	109.5
H1E—N1—H1F	109.5	H8A—C8—H8C	109.5
C4—C3—C2	121.4 (5)	H8B—C8—H8C	109.5
C4—C3—H3	119.3	C12—C13—C14	121.7 (5)
C2—C3—H3	119.3	C12—C13—N2	118.8 (5)
C6—C7—C2	120.9 (5)	C14—C13—N2	119.5 (4)
C6—C7—H7	119.5	C13—N2—H2A	109.5
C2—C7—H7	119.5	C13—N2—H2B	109.5
C6—C5—C4	118.2 (5)	H2A—N2—H2B	109.5
C6—C5—H5	120.9	C13—N2—H2C	109.5
C4—C5—H5	120.9	H2A—N2—H2C	109.5
C3—C2—C7	117.2 (5)	H2B—N2—H2C	109.5
C3—C2—C1	122.4 (5)	C11—C10—C9	121.9 (5)
C7—C2—C1	120.4 (5)	C11—C10—H10	119.1
C3—C4—C5	120.7 (5)	C9—C10—H10	119.1
C3—C4—H4	119.6	C13—C12—C11	117.5 (5)
C5—C4—H4	119.6	C13—C12—H12	121.3
C16—C15—H15A	109.5	C11—C12—H12	121.3
C16—C15—H15B	109.5	C10—C9—C14	116.0 (5)
H15A—C15—H15B	109.5	C10—C9—C8	121.9 (5)
C16—C15—H15C	109.5	C14—C9—C8	122.0 (5)
H15A—C15—H15C	109.5	C13—C14—C9	121.5 (5)
H15B—C15—H15C	109.5	C13—C14—H14	119.3
C18—N3—H3A	109.5	C9—C14—H14	119.3
C18—N3—H3B	109.5	C10—C11—C12	121.4 (5)
H3A—N3—H3B	109.5	C10—C11—H11	119.3
C18—N3—H3C	109.5	C12—C11—H11	119.3
H3A—N3—H3C	109.5	Cl5—Sb1—Cl4	93.76 (5)
H3B—N3—H3C	109.5	Cl5—Sb1—Cl3	87.77 (5)
C17—C18—C19	122.3 (5)	Cl4—Sb1—Cl3	93.52 (5)
C17—C18—N3	118.2 (5)	Cl5—Sb1—Cl6	85.20 (5)
C19—C18—N3	119.4 (5)	Cl4—Sb1—Cl6	89.91 (5)
C21—C16—C17	116.5 (5)	Cl3—Sb1—Cl6	172.36 (4)
C21—C16—C15	123.8 (6)	Cl5—Sb1—Cl2	81.10 (4)
C17—C16—C15	119.6 (6)	Cl4—Sb1—Cl2	174.39 (4)
C18—C17—C16	119.2 (6)	Cl3—Sb1—Cl2	88.54 (4)
C18—C17—H17	120.4	Cl6—Sb1—Cl2	87.44 (4)

C5—C6—C7—C2	0.0 (8)	N3—C18—C19—C20	−177.3 (5)
N1—C6—C7—C2	179.3 (4)	C18—C19—C20—C21	0.7 (9)
C7—C6—C5—C4	−0.3 (7)	C19—C20—C21—C16	−1.0 (10)
N1—C6—C5—C4	−179.6 (4)	C17—C16—C21—C20	0.5 (9)
C4—C3—C2—C7	−0.1 (8)	C15—C16—C21—C20	177.3 (6)
C4—C3—C2—C1	−179.5 (5)	C14—C13—C12—C11	0.7 (8)
C6—C7—C2—C3	0.2 (7)	N2—C13—C12—C11	−178.4 (5)
C6—C7—C2—C1	179.5 (5)	C11—C10—C9—C14	0.1 (9)
C2—C3—C4—C5	−0.2 (8)	C11—C10—C9—C8	−178.7 (6)
C6—C5—C4—C3	0.3 (8)	C12—C13—C14—C9	−0.1 (7)
C19—C18—C17—C16	−0.7 (8)	N2—C13—C14—C9	179.1 (4)
N3—C18—C17—C16	176.8 (4)	C10—C9—C14—C13	−0.4 (7)
C21—C16—C17—C18	0.3 (7)	C8—C9—C14—C13	178.5 (5)
C15—C16—C17—C18	−176.6 (5)	C9—C10—C11—C12	0.6 (10)
C17—C18—C19—C20	0.2 (9)	C13—C12—C11—C10	−1.0 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···Cl1	0.89	2.72	3.602 (4)	169
N1—H1E···Cl6ⁱ	0.89	2.67	3.513 (4)	158
N1—H1F···Cl2ⁱⁱ	0.89	2.59	3.455 (4)	163
N2—H2A···Cl1	0.89	2.37	3.240 (4)	166
N2—H2B···Cl1ⁱⁱⁱ	0.89	2.40	3.249 (4)	160
N2—H2C···Cl2^iv	0.89	2.41	3.238 (4)	155
N3—H3A···Cl1^v	0.89	2.47	3.344 (5)	167
N3—H3B···Cl2ⁱⁱⁱ	0.89	2.56	3.366 (5)	151
N3—H3C···Cl1ⁱⁱⁱ	0.89	2.55	3.355 (5)	151

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

Experimental details

Crystal data
Chemical formula	(C₇H₁₀N)₃[SbCl₅]Cl
M_r	658.93
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	17.171 (3), 9.4065 (19), 20.958 (8)
β (°)	122.36 (2)
V (Å³)	2859.4 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.54
Crystal size (mm)	0.36 × 0.32 × 0.28

Data collection
Diffractometer	Rigaku SCXmini
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.566, 0.640
No. of measured, independent and observed [I > 2σ(I)] reflections	23714, 5029, 3776
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.085, 1.07
No. of reflections	5029
No. of parameters	286
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.57

Computer programs: CrystalClear (Rigaku, 2005), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Sb1—Cl2	3.0319 (14)	Sb1—Cl5	2.4043 (13)
Sb1—Cl3	2.5325 (14)	Sb1—Cl6	2.7779 (14)
Sb1—Cl4	2.4182 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···Cl1	0.89	2.72	3.602 (4)	169
N1—H1E···Cl6ⁱ	0.89	2.67	3.513 (4)	158
N1—H1F···Cl2ⁱⁱ	0.89	2.59	3.455 (4)	163
N2—H2A···Cl1	0.89	2.37	3.240 (4)	166
N2—H2B···Cl1ⁱⁱⁱ	0.89	2.40	3.249 (4)	160
N2—H2C···Cl2^iv	0.89	2.41	3.238 (4)	155
N3—H3A···Cl1^v	0.89	2.47	3.344 (5)	167
N3—H3B···Cl2ⁱⁱⁱ	0.89	2.56	3.366 (5)	151
N3—H3C···Cl1ⁱⁱⁱ	0.89	2.55	3.355 (5)	151

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

Acknowledgements

The author thanks an anonymous advisor from the Ordered Matter Science Research Centre, Southeast University, for great help with the revision of this paper.

References

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