Tris(4-methyl­anilinium) penta­chlorido­anti­monate(III) chloride monohydrate

Xu, Q.

doi:10.1107/S1600536812009427

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page m438

doi:10.1107/S1600536812009427

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Tris(4-methylanilinium) pentachloridoantimonate(III) chloride monohydrate

Qian Xu ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: xqchem@yahoo.com.cn

(Received 27 February 2012; accepted 3 March 2012; online 17 March 2012)

The title compound, (C₇H₁₀N)₃[SbCl₅]Cl·H₂O, consists of 4-methylanilinium cations, Cl⁻ and [SbCl₅]²⁻ anions and water molecules. The five Cl atoms bound to Sb [Sb—Cl = 2.4043 (9)–2.6262 (11) Å] form a square-pyramidal coordination environment. In addition, two [SbCl₅]²⁻ anions related by an inversion center are joined by Sb⋯Cl interactions [Sb⋯Cl = 3.7273 (14) Å] into an [Sb₂Cl₁₀]⁴⁻ dimer with two bridging Cl atoms. The anions, water molecules and ammonium groups of the cations are linked by N—H⋯Cl, N—H⋯O and O—H⋯Cl hydrogen bonds, forming layers parallel to the ac plane. The benzene rings of the 4-methylanilinium cations are packed between these layers.

Related literature

For the closely related structures of bis(anilinium) pentachloridoantimonate(III) and tris(anilinium) chloride pentachloridoantimonate(III) monohydrate, see: Lipka (1980 ) and Chaabouni et al. (2004 ), respectively.

Experimental

Crystal data

(C₇H₁₀N)₃[SbCl₅]Cl·H₂O
M_r = 676.95
Triclinic, $[P \overline 1]$
a = 9.4109 (19) Å
b = 12.867 (3) Å
c = 13.501 (3) Å
α = 63.35 (3)°
β = 83.08 (3)°
γ = 82.51 (3)°
V = 1445.1 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.53 mm⁻¹
T = 293 K
0.31 × 0.25 × 0.22 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.649, T_max = 0.730
15103 measured reflections
6609 independent reflections
6031 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.075
S = 1.06
6609 reflections
304 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯Cl1	0.89	2.32	3.202 (2)	170
N1—H1E⋯Cl1ⁱ	0.89	2.43	3.298 (3)	167
N1—H1F⋯Cl3ⁱ	0.89	2.52	3.381 (2)	162
N2—H2A⋯O1W	0.89	1.97	2.849 (4)	170
N2—H2B⋯Cl3ⁱⁱ	0.89	2.61	3.389 (2)	146
N2—H2C⋯Cl4	0.89	2.45	3.307 (3)	161
N3—H3A⋯Cl1ⁱ	0.89	2.46	3.293 (3)	156
N3—H3B⋯Cl5	0.89	2.51	3.402 (2)	174
N3—H3C⋯Cl1ⁱⁱⁱ	0.89	2.32	3.201 (3)	173
O1W—H1WA⋯Cl4ⁱⁱ	0.85 (1)	2.56 (3)	3.283 (2)	143 (4)
O1W—H1WB⋯Cl2^iv	0.85 (4)	2.69 (3)	3.344 (2)	136 (4)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+1, -z+1; (iii) x-1, y, z; (iv) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812009427/yk2046sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009427/yk2046Isup2.hkl

checkCIF report

Comment top

The title compound was prepared in attempts to synthesize new materials with ferroelectric phase transition. Unfortunately, the dielectric permeability of title compound goes smoothly in the temperature range 80–293 K, suggesting no distinct phase transitions occurred.

A view asymmetric unit of the title compound is shown in Fig. 1. It consists of three p-toluidine cations, one water molecule, and Cl^- and [SbCl₅]^2- anions. Hydrogen bonding between cations, anions and water molecules (Table 1, Fig. 2) produces two-dimensional network parallel to the ac plane. Analogous system of hydrogen bonds exists in closely related structure of tris-anilinium chloride pentachloroantimonate (III) monohydrate (Chaabouni et al., 2004)

The Sb atom is coordinated by five Cl atoms in a slightly distorted square-pyramidal mode. The distance from Sb to the apical Cl atom is much shorter than the equatorial Sb—Cl bonds. Such structure is typical of [SbCl₅]^2--containing salts (Lipka, 1980). Two anions [SbCl₅]^2- related by an inversion center are joined by Sb···Cl interactions [Sb···Cl = 3.7273 (14) Å] into the Sb₂Cl₁₀^4- dimer with two bridging Cl atoms.

Related literature top

For the closely related structures of bis(anilinium) pentachloroantimonate(III) and tris(anilinium) chloride pentachloroantimonate(III) monohydrate, see: Lipka (1980) and Chaabouni et al. (2004), respectively.

Experimental top

The mixture of SbCl₃ (1.1 g, 5 mmol) and p-toluidine (1.05 g, 10 mmol) was dissolved in hydrochloric acid and stirred for several minutes at room temperature. Colorless crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of the solution at room temperature over 2 weeks.

Structure description top

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound with atom labelling scheme and thermal ellipsoids drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The system of hydrogen bonds (shown as dashed lines) in the title compound.

Tris(4-methylanilinium) pentachloridoantimonate(III) chloride monohydrate top

Crystal data top

(C₇H₁₀N)₃[SbCl₅]Cl·H₂O	Z = 2
M_r = 676.95	F(000) = 680
Triclinic, P1	D_x = 1.556 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4109 (19) Å	Cell parameters from 6609 reflections
b = 12.867 (3) Å	θ = 2.3–27.5°
c = 13.501 (3) Å	µ = 1.53 mm⁻¹
α = 63.35 (3)°	T = 293 K
β = 83.08 (3)°	Block, brown
γ = 82.51 (3)°	0.31 × 0.25 × 0.22 mm
V = 1445.1 (5) Å³

Data collection top

Rigaku SCXmini diffractometer	6609 independent reflections
Radiation source: fine-focus sealed tube	6031 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −12→12
T_min = 0.649, T_max = 0.730	k = −16→16
15103 measured reflections	l = −17→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.075	w = 1/[σ²(F_o²) + (0.0383P)² + 0.2569P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.041
6609 reflections	Δρ_max = 0.45 e Å⁻³
304 parameters	Δρ_min = −0.63 e Å⁻³
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0277 (8)

Crystal data top

(C₇H₁₀N)₃[SbCl₅]Cl·H₂O	γ = 82.51 (3)°
M_r = 676.95	V = 1445.1 (5) Å³
Triclinic, P1	Z = 2
a = 9.4109 (19) Å	Mo Kα radiation
b = 12.867 (3) Å	µ = 1.53 mm⁻¹
c = 13.501 (3) Å	T = 293 K
α = 63.35 (3)°	0.31 × 0.25 × 0.22 mm
β = 83.08 (3)°

Data collection top

Rigaku SCXmini diffractometer	6609 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	6031 reflections with I > 2σ(I)
T_min = 0.649, T_max = 0.730	R_int = 0.029
15103 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	3 restraints
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.45 e Å⁻³
6609 reflections	Δρ_min = −0.63 e Å⁻³
304 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.5819 (5)	−0.1182 (3)	0.1786 (3)	0.0788 (11)
H1A	0.6179	−0.1519	0.1289	0.118*
H1B	0.4873	−0.1416	0.2087	0.118*
H1C	0.6445	−0.1446	0.2379	0.118*
C2	0.5756 (3)	0.0133 (2)	0.1160 (2)	0.0491 (6)
C3	0.4543 (4)	0.0833 (3)	0.1201 (3)	0.0681 (9)
H3	0.3746	0.0492	0.1655	0.082*
C4	0.4473 (3)	0.2033 (3)	0.0584 (3)	0.0599 (8)
H4	0.3635	0.2493	0.0612	0.072*
C5	0.5651 (3)	0.2528 (2)	−0.00645 (19)	0.0379 (5)
C6	0.6881 (3)	0.1871 (2)	−0.0109 (3)	0.0553 (7)
H6	0.7685	0.2219	−0.0545	0.066*
C7	0.6920 (4)	0.0668 (2)	0.0508 (3)	0.0614 (8)
H7	0.7761	0.0214	0.0476	0.074*
C8	0.7153 (4)	−0.0700 (3)	0.4215 (4)	0.0913 (13)
H8A	0.8016	−0.1084	0.4582	0.137*
H8B	0.7278	−0.0594	0.3460	0.137*
H8C	0.6367	−0.1169	0.4594	0.137*
C9	0.6836 (3)	0.0481 (3)	0.4229 (3)	0.0570 (8)
C10	0.6689 (3)	0.0565 (3)	0.5211 (3)	0.0636 (8)
H10	0.6762	−0.0115	0.5872	0.076*
C11	0.6434 (3)	0.1633 (2)	0.5252 (2)	0.0522 (7)
H11	0.6358	0.1673	0.5927	0.063*
C12	0.6420 (3)	0.2577 (2)	0.3272 (2)	0.0486 (6)
H12	0.6318	0.3255	0.2613	0.058*
C13	0.6697 (3)	0.1498 (3)	0.3258 (3)	0.0595 (8)
H13	0.6791	0.1459	0.2582	0.071*
C14	0.0597 (5)	−0.1055 (3)	0.2261 (4)	0.0835 (11)
H14A	−0.0081	−0.1487	0.2850	0.125*
H14B	0.1549	−0.1419	0.2437	0.125*
H14C	0.0376	−0.1044	0.1580	0.125*
C15	0.0512 (3)	0.0175 (2)	0.2129 (3)	0.0520 (7)
C16	0.0510 (3)	0.0397 (2)	0.3037 (2)	0.0548 (7)
H16	0.0582	−0.0228	0.3738	0.066*
C17	0.0403 (3)	0.1524 (2)	0.2937 (2)	0.0504 (6)
H17	0.0406	0.1655	0.3561	0.060*
C18	0.0292 (2)	0.2445 (2)	0.1900 (2)	0.0379 (5)
C19	0.0306 (3)	0.2262 (2)	0.0970 (2)	0.0509 (7)
H19	0.0239	0.2889	0.0271	0.061*
C20	0.0423 (4)	0.1126 (3)	0.1097 (3)	0.0597 (8)
H20	0.0443	0.0997	0.0470	0.072*
C21	0.6298 (2)	0.2630 (2)	0.4271 (2)	0.0382 (5)
Cl6	0.28747 (6)	0.39064 (5)	0.30055 (5)	0.03994 (14)
Cl3	0.34735 (7)	0.63633 (5)	0.32019 (5)	0.04439 (14)
Cl2	0.02743 (7)	0.61394 (6)	0.19317 (5)	0.04800 (15)
Cl4	0.27679 (8)	0.36960 (6)	0.56178 (5)	0.05163 (16)
Cl5	−0.04581 (7)	0.34297 (6)	0.43914 (6)	0.04692 (15)
N1	0.5587 (2)	0.38021 (17)	−0.07764 (17)	0.0446 (5)
H1D	0.6201	0.4117	−0.0559	0.067*
H1E	0.4701	0.4118	−0.0718	0.067*
H1F	0.5820	0.3938	−0.1480	0.067*
N2	0.5985 (2)	0.37651 (19)	0.43079 (19)	0.0467 (5)
H2A	0.6203	0.4335	0.3642	0.070*
H2B	0.6507	0.3784	0.4806	0.070*
H2C	0.5056	0.3862	0.4498	0.070*
N3	0.0109 (2)	0.36535 (18)	0.17691 (19)	0.0454 (5)
H3A	0.0890	0.4014	0.1407	0.068*
H3B	−0.0019	0.3647	0.2436	0.068*
H3C	−0.0653	0.4029	0.1385	0.068*
Sb1	0.137115 (15)	0.499310 (12)	0.384947 (11)	0.03139 (7)
Cl1	0.74902 (6)	0.49450 (5)	0.02248 (5)	0.04278 (14)
O1W	0.6775 (2)	0.5732 (2)	0.23099 (19)	0.0591 (5)
H1WA	0.686 (5)	0.620 (4)	0.258 (4)	0.129 (18)*
H1WB	0.758 (3)	0.562 (4)	0.200 (4)	0.14 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.126 (3)	0.0427 (16)	0.059 (2)	−0.0255 (19)	−0.015 (2)	−0.0082 (14)
C2	0.0684 (18)	0.0365 (13)	0.0381 (14)	−0.0169 (13)	−0.0052 (12)	−0.0091 (11)
C3	0.0575 (19)	0.0624 (19)	0.064 (2)	−0.0254 (16)	0.0151 (15)	−0.0092 (15)
C4	0.0463 (15)	0.0519 (17)	0.0643 (19)	−0.0039 (13)	0.0102 (13)	−0.0138 (14)
C5	0.0428 (13)	0.0362 (12)	0.0348 (12)	−0.0074 (10)	−0.0032 (10)	−0.0146 (10)
C6	0.0432 (14)	0.0420 (14)	0.0656 (19)	−0.0089 (12)	0.0110 (13)	−0.0125 (13)
C7	0.0587 (18)	0.0377 (14)	0.073 (2)	0.0026 (13)	0.0010 (15)	−0.0146 (14)
C8	0.063 (2)	0.061 (2)	0.167 (4)	−0.0060 (18)	−0.007 (2)	−0.066 (3)
C9	0.0355 (13)	0.0500 (16)	0.092 (2)	−0.0043 (12)	−0.0065 (14)	−0.0361 (16)
C10	0.0588 (18)	0.0506 (17)	0.068 (2)	−0.0120 (14)	−0.0118 (15)	−0.0110 (15)
C11	0.0547 (16)	0.0536 (16)	0.0476 (16)	−0.0097 (13)	−0.0041 (12)	−0.0204 (13)
C12	0.0460 (14)	0.0525 (16)	0.0477 (15)	−0.0012 (12)	−0.0047 (11)	−0.0228 (12)
C13	0.0535 (17)	0.072 (2)	0.070 (2)	−0.0007 (15)	−0.0069 (14)	−0.0470 (17)
C14	0.094 (3)	0.054 (2)	0.102 (3)	0.0050 (19)	−0.003 (2)	−0.038 (2)
C15	0.0428 (14)	0.0463 (15)	0.0651 (18)	0.0038 (12)	−0.0050 (13)	−0.0245 (13)
C16	0.0547 (16)	0.0446 (15)	0.0519 (17)	−0.0005 (13)	−0.0095 (13)	−0.0091 (12)
C17	0.0586 (16)	0.0506 (15)	0.0418 (14)	−0.0059 (13)	−0.0096 (12)	−0.0184 (12)
C18	0.0321 (11)	0.0394 (12)	0.0441 (13)	−0.0036 (10)	−0.0078 (10)	−0.0186 (10)
C19	0.0662 (18)	0.0444 (14)	0.0394 (14)	−0.0025 (13)	−0.0103 (12)	−0.0150 (11)
C20	0.076 (2)	0.0608 (18)	0.0523 (17)	0.0000 (16)	−0.0066 (15)	−0.0344 (15)
C21	0.0283 (11)	0.0415 (13)	0.0487 (14)	−0.0063 (10)	−0.0029 (10)	−0.0225 (11)
Cl6	0.0361 (3)	0.0465 (3)	0.0429 (3)	−0.0003 (2)	0.0002 (2)	−0.0262 (3)
Cl3	0.0448 (3)	0.0446 (3)	0.0474 (3)	−0.0162 (3)	0.0032 (3)	−0.0218 (3)
Cl2	0.0510 (4)	0.0476 (3)	0.0368 (3)	−0.0034 (3)	−0.0084 (3)	−0.0099 (3)
Cl4	0.0647 (4)	0.0520 (4)	0.0348 (3)	0.0012 (3)	−0.0120 (3)	−0.0156 (3)
Cl5	0.0387 (3)	0.0489 (3)	0.0551 (4)	−0.0166 (3)	0.0054 (3)	−0.0233 (3)
N1	0.0557 (13)	0.0341 (10)	0.0411 (12)	−0.0069 (9)	−0.0067 (9)	−0.0124 (9)
N2	0.0415 (11)	0.0518 (13)	0.0542 (13)	−0.0025 (10)	−0.0072 (10)	−0.0293 (11)
N3	0.0459 (12)	0.0422 (11)	0.0508 (13)	−0.0045 (10)	−0.0130 (10)	−0.0202 (10)
Sb1	0.02980 (10)	0.03616 (10)	0.02999 (10)	−0.00388 (6)	0.00011 (6)	−0.01637 (7)
Cl1	0.0404 (3)	0.0455 (3)	0.0445 (3)	−0.0007 (3)	−0.0049 (2)	−0.0220 (3)
O1W	0.0567 (13)	0.0671 (14)	0.0617 (13)	−0.0053 (11)	−0.0021 (10)	−0.0361 (11)

Geometric parameters (Å, º) top

C1—C2	1.511 (4)	C14—H14B	0.9600
C1—H1A	0.9600	C14—H14C	0.9600
C1—H1B	0.9600	C15—C16	1.377 (4)
C1—H1C	0.9600	C15—C20	1.385 (4)
C2—C7	1.367 (4)	C16—C17	1.386 (4)
C2—C3	1.371 (5)	C16—H16	0.9300
C3—C4	1.385 (4)	C17—C18	1.375 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.360 (4)	C18—C19	1.376 (3)
C4—H4	0.9300	C18—N3	1.473 (3)
C5—C6	1.353 (4)	C19—C20	1.385 (4)
C5—N1	1.480 (3)	C19—H19	0.9300
C6—C7	1.388 (4)	C20—H20	0.9300
C6—H6	0.9300	C21—N2	1.474 (3)
C7—H7	0.9300	Cl6—Sb1	2.4043 (9)
C8—C9	1.518 (4)	Cl3—Sb1	2.6262 (11)
C8—H8A	0.9600	Cl2—Sb1	2.6011 (12)
C8—H8B	0.9600	Cl4—Sb1	2.6120 (13)
C8—H8C	0.9600	Cl5—Sb1	2.6124 (11)
C9—C10	1.367 (5)	N1—H1D	0.8900
C9—C13	1.380 (5)	N1—H1E	0.8900
C10—C11	1.389 (4)	N1—H1F	0.8900
C10—H10	0.9300	N2—H2A	0.8900
C11—C21	1.375 (4)	N2—H2B	0.8900
C11—H11	0.9300	N2—H2C	0.8900
C12—C21	1.371 (3)	N3—H3A	0.8900
C12—C13	1.387 (4)	N3—H3B	0.8900
C12—H12	0.9300	N3—H3C	0.8900
C13—H13	0.9300	O1W—H1WA	0.845 (10)
C14—C15	1.504 (4)	O1W—H1WB	0.847 (10)
C14—H14A	0.9600

C2—C1—H1A	109.5	C16—C15—C20	117.5 (3)
C2—C1—H1B	109.5	C16—C15—C14	121.0 (3)
H1A—C1—H1B	109.5	C20—C15—C14	121.5 (3)
C2—C1—H1C	109.5	C15—C16—C17	121.9 (3)
H1A—C1—H1C	109.5	C15—C16—H16	119.0
H1B—C1—H1C	109.5	C17—C16—H16	119.0
C7—C2—C3	117.4 (2)	C18—C17—C16	118.8 (3)
C7—C2—C1	120.5 (3)	C18—C17—H17	120.6
C3—C2—C1	122.2 (3)	C16—C17—H17	120.6
C2—C3—C4	121.8 (3)	C17—C18—C19	121.1 (2)
C2—C3—H3	119.1	C17—C18—N3	120.3 (2)
C4—C3—H3	119.1	C19—C18—N3	118.6 (2)
C5—C4—C3	118.8 (3)	C18—C19—C20	118.7 (2)
C5—C4—H4	120.6	C18—C19—H19	120.7
C3—C4—H4	120.6	C20—C19—H19	120.7
C6—C5—C4	121.3 (2)	C15—C20—C19	121.9 (3)
C6—C5—N1	118.6 (2)	C15—C20—H20	119.0
C4—C5—N1	120.1 (2)	C19—C20—H20	119.0
C5—C6—C7	118.8 (3)	C12—C21—C11	121.0 (2)
C5—C6—H6	120.6	C12—C21—N2	120.1 (2)
C7—C6—H6	120.6	C11—C21—N2	118.9 (2)
C2—C7—C6	121.9 (3)	C5—N1—H1D	109.5
C2—C7—H7	119.0	C5—N1—H1E	109.5
C6—C7—H7	119.0	H1D—N1—H1E	109.5
C9—C8—H8A	109.5	C5—N1—H1F	109.5
C9—C8—H8B	109.5	H1D—N1—H1F	109.5
H8A—C8—H8B	109.5	H1E—N1—H1F	109.5
C9—C8—H8C	109.5	C21—N2—H2A	109.5
H8A—C8—H8C	109.5	C21—N2—H2B	109.5
H8B—C8—H8C	109.5	H2A—N2—H2B	109.5
C10—C9—C13	118.1 (3)	C21—N2—H2C	109.5
C10—C9—C8	120.5 (3)	H2A—N2—H2C	109.5
C13—C9—C8	121.4 (3)	H2B—N2—H2C	109.5
C9—C10—C11	122.0 (3)	C18—N3—H3A	109.5
C9—C10—H10	119.0	C18—N3—H3B	109.5
C11—C10—H10	119.0	H3A—N3—H3B	109.5
C21—C11—C10	118.5 (3)	C18—N3—H3C	109.5
C21—C11—H11	120.8	H3A—N3—H3C	109.5
C10—C11—H11	120.8	H3B—N3—H3C	109.5
C21—C12—C13	119.1 (3)	Cl6—Sb1—Cl2	85.80 (4)
C21—C12—H12	120.5	Cl6—Sb1—Cl4	85.36 (3)
C13—C12—H12	120.5	Cl2—Sb1—Cl4	171.07 (2)
C9—C13—C12	121.3 (3)	Cl6—Sb1—Cl5	86.20 (3)
C9—C13—H13	119.4	Cl2—Sb1—Cl5	88.98 (4)
C12—C13—H13	119.4	Cl4—Sb1—Cl5	91.76 (4)
C15—C14—H14A	109.5	Cl6—Sb1—Cl3	85.26 (3)
C15—C14—H14B	109.5	Cl2—Sb1—Cl3	91.42 (4)
H14A—C14—H14B	109.5	Cl4—Sb1—Cl3	86.53 (4)
C15—C14—H14C	109.5	Cl5—Sb1—Cl3	171.40 (2)
H14A—C14—H14C	109.5	H1WA—O1W—H1WB	109 (2)
H14B—C14—H14C	109.5

C7—C2—C3—C4	1.8 (5)	C21—C12—C13—C9	0.7 (4)
C1—C2—C3—C4	−176.9 (3)	C20—C15—C16—C17	0.9 (4)
C2—C3—C4—C5	−1.1 (5)	C14—C15—C16—C17	−178.7 (3)
C3—C4—C5—C6	−0.4 (5)	C15—C16—C17—C18	0.2 (4)
C3—C4—C5—N1	176.9 (3)	C16—C17—C18—C19	−1.0 (4)
C4—C5—C6—C7	1.1 (5)	C16—C17—C18—N3	177.2 (2)
N1—C5—C6—C7	−176.3 (3)	C17—C18—C19—C20	0.6 (4)
C3—C2—C7—C6	−1.1 (5)	N3—C18—C19—C20	−177.6 (3)
C1—C2—C7—C6	177.6 (3)	C16—C15—C20—C19	−1.3 (5)
C5—C6—C7—C2	−0.3 (5)	C14—C15—C20—C19	178.2 (3)
C13—C9—C10—C11	−1.2 (4)	C18—C19—C20—C15	0.6 (5)
C8—C9—C10—C11	178.4 (3)	C13—C12—C21—C11	−0.5 (4)
C9—C10—C11—C21	1.4 (4)	C13—C12—C21—N2	−179.2 (2)
C10—C9—C13—C12	0.2 (4)	C10—C11—C21—C12	−0.5 (4)
C8—C9—C13—C12	−179.4 (3)	C10—C11—C21—N2	178.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···Cl1	0.89	2.32	3.202 (2)	170
N1—H1E···Cl1ⁱ	0.89	2.43	3.298 (3)	167
N1—H1F···Cl3ⁱ	0.89	2.52	3.381 (2)	162
N2—H2A···O1W	0.89	1.97	2.849 (4)	170
N2—H2B···Cl3ⁱⁱ	0.89	2.61	3.389 (2)	146
N2—H2C···Cl4	0.89	2.45	3.307 (3)	161
N3—H3A···Cl1ⁱ	0.89	2.46	3.293 (3)	156
N3—H3B···Cl5	0.89	2.51	3.402 (2)	174
N3—H3C···Cl1ⁱⁱⁱ	0.89	2.32	3.201 (3)	173
O1W—H1WA···Cl4ⁱⁱ	0.85 (1)	2.56 (3)	3.283 (2)	143 (4)
O1W—H1WB···Cl2^iv	0.85 (4)	2.69 (3)	3.344 (2)	136 (4)

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

Experimental details

Crystal data
Chemical formula	(C₇H₁₀N)₃[SbCl₅]Cl·H₂O
M_r	676.95
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.4109 (19), 12.867 (3), 13.501 (3)
α, β, γ (°)	63.35 (3), 83.08 (3), 82.51 (3)
V (Å³)	1445.1 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.53
Crystal size (mm)	0.31 × 0.25 × 0.22

Data collection
Diffractometer	Rigaku SCXmini
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.649, 0.730
No. of measured, independent and observed [I > 2σ(I)] reflections	15103, 6609, 6031
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.075, 1.06
No. of reflections	6609
No. of parameters	304
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.63

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···Cl1	0.89	2.32	3.202 (2)	170.3
N1—H1E···Cl1ⁱ	0.89	2.43	3.298 (3)	166.5
N1—H1F···Cl3ⁱ	0.89	2.52	3.381 (2)	162.1
N2—H2A···O1W	0.89	1.97	2.849 (4)	170.2
N2—H2B···Cl3ⁱⁱ	0.89	2.61	3.389 (2)	146.3
N2—H2C···Cl4	0.89	2.45	3.307 (3)	161.4
N3—H3A···Cl1ⁱ	0.89	2.46	3.293 (3)	156.1
N3—H3B···Cl5	0.89	2.51	3.402 (2)	174.3
N3—H3C···Cl1ⁱⁱⁱ	0.89	2.32	3.201 (3)	173.2
O1W—H1WA···Cl4ⁱⁱ	0.845 (10)	2.56 (3)	3.283 (2)	143 (4)
O1W—H1WB···Cl2^iv	0.85 (4)	2.69 (3)	3.344 (2)	136 (4)

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

Acknowledgements

This work was supported by Southeast University.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Chaabouni, S., Savariault, J. M. & Salah, H. (2004). J. Chem. Crystallogr. 34, 661–664. Web of Science CSD CrossRef CAS Google Scholar
Lipka, A. (1980). Z. Anorg. Allg. Chem. 469, 218–228. CSD CrossRef CAS Web of Science Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar