Hexa­kis­(4-acetyl­pyridinium) octa­deca­chloridotetra­anti­monate(III)

Fu, X.

doi:10.1107/S160053681002057X

metal-organic compounds

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Volume 66| Part 7| July 2010| Page m736

doi:10.1107/S160053681002057X

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Hexakis(4-acetylpyridinium) octadecachloridotetraantimonate(III)

Xue-qun Fu ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: fuxuequn222@163.com

(Received 10 May 2010; accepted 31 May 2010; online 5 June 2010)

The title compound, (C₇H₈NO)₆[Sb₄Cl₁₈], contains centrosymmetric hexaanions built up from four vertex-sharing alternating SbCl₅ square-based pyramids and highly distorted SbCl₆ octahedra when long (<3.2 Å) `secondary' Sb—Cl interactions are taken into account. The inter-polyhedral Sb—Cl bonds define a square-shape. In the crystal, the components are linked by N—H⋯Cl, C—H⋯Cl and C—H⋯O hydrogen bonds, generating a three-dimensional network.

Related literature

For general background to phase transitions in coordination networks, see: Li et al. (2008 ); Zhang et al. (2009 ). For crystal structures containing the 4-acetylpyridinium cation, see: Fu (2009a ,b ); Majerz et al. (1991 ); Pang et al. (1994 ); Steffen & Palenik (1977 ).

Experimental

Crystal data

(C₇H₈NO)₆[Sb₄Cl₁₈]
M_r = 1857.96
Triclinic, $[P \overline 1]$
a = 9.0589 (18) Å
b = 13.838 (3) Å
c = 15.128 (3) Å
α = 108.29 (3)°
β = 98.00 (3)°
γ = 107.10 (3)°
V = 1664.1 (6) Å³
Z = 1
Mo Kα radiation
μ = 2.37 mm⁻¹
T = 298 K
0.40 × 0.30 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.430, T_max = 0.622
17638 measured reflections
7613 independent reflections
6371 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.070
S = 1.04
7613 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Selected bond lengths (Å)

Sb1—Cl4	2.4036 (9)
Sb1—Cl3	2.4107 (10)
Sb1—Cl2	2.4113 (14)
Sb1—Cl1	2.9359 (12)
Sb1—Cl5	3.0214 (12)
Sb1—Cl6ⁱ	3.1275 (12)
Sb2—Cl7	2.3516 (12)
Sb2—Cl8	2.4459 (10)
Sb2—Cl9	2.4498 (10)
Sb2—Cl5	2.8352 (11)
Sb2—Cl6	2.8937 (11)
Symmetry code: (i) -x+2, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl6	0.86	2.30	3.148 (3)	170
N1—H1D⋯Cl1ⁱⁱ	0.86	2.20	3.056 (3)	174
N3—H3A⋯Cl5ⁱⁱⁱ	0.86	2.35	3.198 (3)	168
C1—H1A⋯O2^iv	0.96	2.60	3.506 (5)	158
C5—H5A⋯Cl8^v	0.93	2.78	3.585 (4)	146
C13—H13A⋯Cl1ⁱ	0.93	2.76	3.661 (4)	162
C19—H19A⋯Cl7ⁱⁱⁱ	0.93	2.67	3.449 (4)	141
C21—H21A⋯O1ⁱⁱⁱ	0.93	2.42	3.349 (4)	177
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x, y, z-1; (iii) -x+1, -y+1, -z+1; (iv) x, y-1, z; (v) x, y-1, z-1.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681002057X/hb5440sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681002057X/hb5440Isup2.hkl

checkCIF report

Comment top

As a continuation of our study of phase transition materials, including organic ligands (Li et al., 2008), metal-organic coordination compounds (Zhang et al., 2009), organic-inorganic hybrids, we studied the dielectric properties of the title compound, unfortunately, there was no distinct anomaly observed from 93 K to 400 K, (m.p. 421–423 K), suggesting that this compound should be not a real ferroelectrics or there may be no distinct phase transition occurred within the measured temperature range. In this article, the crystal structure of (I) has been presented.

4-Acetylpyridine may be used as a ligand in coordination compounds e.g. with Zn (Steffen & Palenik, 1977) or Ni (Pang et al., 1994). The crystal structures of 4-acetylpyridine together with inorganic acids are also known e.g. with sulfuric acid (Fu, 2009b) and perchloric acid (Fu, 2009a).

The cell unit of the title compound is made up of six almost planar protonated 4-acetylpyridinium cations and a [Sb₄Cl₁₈]^6- anion (Fig. 1.).In the coordinate anion of [Sb₄Cl₁₈]^6-, antimony(III) atoms have two kinds of coordination pattern. Sb³⁺(2) coordinated with five Cl ions construct a distorted tetragonal pyramidal structure, composing two briding and three terminal Cl atoms. There are Cl—Sb secondary bonds by the linkage between the Sb³⁺(1)···Cl5 and Sb³⁺(1)···Cl6, with the bond lengths of these secondary bonds 3.0210 (11)Å and 3.1280 (11) Å, respectively, compared to the normal coordination bonds of Sb—Cl 2.3516 (12)Å to 2.8937 (11) Å. Owing to these secondary bonds, the coordination number of the central ion Sb³⁺(1) increases to six, and it adopts a distorted octahedral geometry.

The tridimensional network arrangement in the crystal structure of (I) is mainly determined by relatively strong and directional hydrogen bonds (Table. 1),

Related literature top

For general background to phase transitions in coordination networks, see: Li et al. (2008); Zhang et al. (2009). For crystal structures containing the 4-acetylpyridinium cation, see: Fu (2009a,b); Majerz et al. (1991); Pang et al. (1994); Steffen & Palenik (1977).

Experimental top

2.28 g (10 mmol) SbCl₃ was firstly dissolved in 10 ml 1:1 HCl solution, to which 2.42 g (20 mmol) 4-acetylpyridine ethanol solution was then added under stirring. Hydrochloric acid was added until the precipitated substrates disappeared. The acid solution was allowed to slowly evaporate at room temperature until colorless prisms of (I) were grown.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level (all H atoms have been omitted for clarity). Unlabelled atoms are generated by the symmetry operation (2–x, 1–y, 1–z).
	Fig. 2. A view of the packing of (I), stacking along the a axis. Dashed lines indicate hydrogen bonds.

Hexakis(4-acetylpyridinium) octadecachloridotetraantimonate(III) top

Crystal data top

(C₇H₈NO)₆[Sb₄Cl₁₈]	Z = 1
M_r = 1857.96	F(000) = 900
Triclinic, P1	D_x = 1.854 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0589 (18) Å	Cell parameters from 8056 reflections
b = 13.838 (3) Å	θ = 3.1–27.7°
c = 15.128 (3) Å	µ = 2.37 mm⁻¹
α = 108.29 (3)°	T = 298 K
β = 98.00 (3)°	Prism, colourless
γ = 107.10 (3)°	0.40 × 0.30 × 0.20 mm
V = 1664.1 (6) Å³

Data collection top

Rigaku SCXmini diffractometer	7613 independent reflections
Radiation source: fine-focus sealed tube	6371 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −17→17
T_min = 0.430, T_max = 0.622	l = −19→19
17638 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0307P)² + 0.5066P] where P = (F_o² + 2F_c²)/3
7613 reflections	(Δ/σ)_max = 0.001
343 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

(C₇H₈NO)₆[Sb₄Cl₁₈]	γ = 107.10 (3)°
M_r = 1857.96	V = 1664.1 (6) Å³
Triclinic, P1	Z = 1
a = 9.0589 (18) Å	Mo Kα radiation
b = 13.838 (3) Å	µ = 2.37 mm⁻¹
c = 15.128 (3) Å	T = 298 K
α = 108.29 (3)°	0.40 × 0.30 × 0.20 mm
β = 98.00 (3)°

Data collection top

Rigaku SCXmini diffractometer	7613 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	6371 reflections with I > 2σ(I)
T_min = 0.430, T_max = 0.622	R_int = 0.028
17638 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 1.04	Δρ_max = 0.39 e Å⁻³
7613 reflections	Δρ_min = −0.38 e Å⁻³
343 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
O1	0.7595 (3)	0.1417 (2)	0.15768 (17)	0.0544 (6)
N1	0.9897 (4)	0.2973 (3)	−0.0627 (2)	0.0573 (8)
H1D	1.0377	0.3389	−0.0898	0.069*
C3	0.8404 (4)	0.1681 (3)	0.0233 (2)	0.0408 (7)
C6	0.9436 (5)	0.3405 (3)	0.0152 (3)	0.0574 (10)
H6A	0.9616	0.4147	0.0386	0.069*
C4	0.8871 (4)	0.1248 (3)	−0.0588 (2)	0.0490 (8)
H4A	0.8660	0.0503	−0.0855	0.059*
C7	0.8713 (4)	0.2783 (3)	0.0610 (3)	0.0525 (9)
H7A	0.8428	0.3094	0.1169	0.063*
C5	0.9634 (5)	0.1912 (3)	−0.0998 (2)	0.0557 (9)
H5A	0.9976	0.1629	−0.1540	0.067*
C2	0.7623 (4)	0.0986 (3)	0.0748 (3)	0.0497 (8)
Sb1	0.86744 (2)	0.350428 (15)	0.674838 (14)	0.03137 (6)
Cl4	0.83619 (12)	0.17158 (6)	0.67419 (6)	0.0519 (2)
Cl3	0.74694 (11)	0.39130 (8)	0.80769 (6)	0.0528 (2)
Cl2	0.61006 (10)	0.27520 (7)	0.56102 (6)	0.0543 (2)
C1	0.6945 (7)	−0.0208 (3)	0.0234 (4)	0.110 (2)
H1A	0.6487	−0.0545	0.0648	0.165*
H1B	0.7775	−0.0467	0.0054	0.165*
H1C	0.6133	−0.0390	−0.0333	0.165*
Cl1	1.15940 (10)	0.43033 (7)	0.82937 (7)	0.0529 (2)
Sb2	0.93951 (2)	0.785682 (15)	0.693125 (14)	0.03208 (6)
Cl7	0.67862 (9)	0.73910 (7)	0.60241 (6)	0.0474 (2)
Cl9	0.83859 (11)	0.82021 (8)	0.83764 (6)	0.0544 (2)
Cl8	0.99930 (12)	0.97530 (7)	0.70831 (7)	0.0595 (2)
Cl5	0.86213 (12)	0.56019 (7)	0.65539 (7)	0.0577 (2)
Cl6	1.00732 (11)	0.73440 (8)	0.50601 (6)	0.0557 (2)
C10	0.6128 (4)	0.9155 (3)	0.3188 (2)	0.0436 (8)
C14	0.6375 (4)	0.8208 (3)	0.2737 (3)	0.0525 (9)
H14A	0.5913	0.7814	0.2082	0.063*
N2	0.7927 (4)	0.8408 (3)	0.4180 (3)	0.0584 (8)
H2A	0.8511	0.8172	0.4493	0.070*
C12	0.7702 (5)	0.9308 (3)	0.4648 (3)	0.0595 (10)
H12A	0.8150	0.9669	0.5308	0.071*
C11	0.6807 (4)	0.9711 (3)	0.4161 (3)	0.0512 (9)
H11A	0.6659	1.0355	0.4484	0.061*
C13	0.7289 (5)	0.7851 (3)	0.3245 (3)	0.0610 (10)
H13A	0.7471	0.7216	0.2939	0.073*
O2	0.4633 (4)	0.9034 (3)	0.1749 (2)	0.0794 (9)
C9	0.5172 (4)	0.9568 (3)	0.2594 (3)	0.0537 (9)
C8	0.4958 (6)	1.0602 (4)	0.3054 (3)	0.0865 (15)
H8A	0.4326	1.0748	0.2582	0.130*
H8B	0.5982	1.1180	0.3327	0.130*
H8C	0.4424	1.0555	0.3553	0.130*
C18	0.4716 (4)	0.5259 (3)	0.7037 (3)	0.0540 (9)
H18A	0.5403	0.4988	0.7313	0.065*
N3	0.3089 (4)	0.5204 (3)	0.5680 (2)	0.0584 (8)
H3A	0.2674	0.4905	0.5069	0.070*
C17	0.4345 (4)	0.6097 (2)	0.7603 (2)	0.0418 (7)
C16	0.4972 (4)	0.6600 (3)	0.8688 (3)	0.0587 (10)
C21	0.3347 (4)	0.6486 (3)	0.7166 (3)	0.0537 (9)
H21A	0.3100	0.7066	0.7534	0.064*
C15	0.5935 (6)	0.6125 (4)	0.9162 (3)	0.0897 (15)
H15A	0.6250	0.6526	0.9845	0.135*
H15B	0.6870	0.6161	0.8924	0.135*
H15C	0.5314	0.5377	0.9027	0.135*
C20	0.2716 (5)	0.6023 (3)	0.6191 (3)	0.0588 (10)
H20A	0.2035	0.6280	0.5892	0.071*
O3	0.4681 (4)	0.7375 (2)	0.9125 (2)	0.0803 (9)
C19	0.4076 (5)	0.4828 (3)	0.6073 (3)	0.0642 (11)
H19A	0.4332	0.4264	0.5686	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0600 (16)	0.0584 (15)	0.0478 (14)	0.0245 (12)	0.0219 (12)	0.0173 (12)
N1	0.068 (2)	0.063 (2)	0.0528 (19)	0.0261 (16)	0.0166 (16)	0.0331 (17)
C3	0.0408 (17)	0.0425 (18)	0.0348 (17)	0.0151 (14)	0.0048 (13)	0.0109 (15)
C6	0.075 (3)	0.046 (2)	0.058 (2)	0.0281 (19)	0.023 (2)	0.0205 (19)
C4	0.065 (2)	0.0417 (19)	0.0358 (18)	0.0204 (17)	0.0090 (16)	0.0096 (15)
C7	0.060 (2)	0.049 (2)	0.050 (2)	0.0259 (17)	0.0191 (17)	0.0118 (17)
C5	0.076 (3)	0.060 (2)	0.0344 (18)	0.031 (2)	0.0144 (18)	0.0157 (18)
C2	0.050 (2)	0.047 (2)	0.048 (2)	0.0174 (16)	0.0158 (16)	0.0107 (17)
Sb1	0.03433 (11)	0.03025 (11)	0.03262 (11)	0.01447 (8)	0.00818 (8)	0.01327 (9)
Cl4	0.0760 (6)	0.0343 (4)	0.0502 (5)	0.0230 (4)	0.0131 (4)	0.0206 (4)
Cl3	0.0535 (5)	0.0654 (6)	0.0479 (5)	0.0294 (4)	0.0235 (4)	0.0201 (4)
Cl2	0.0417 (4)	0.0604 (5)	0.0524 (5)	0.0143 (4)	−0.0025 (4)	0.0199 (4)
C1	0.156 (5)	0.050 (3)	0.100 (4)	0.001 (3)	0.076 (4)	0.012 (3)
Cl1	0.0454 (5)	0.0531 (5)	0.0556 (5)	0.0120 (4)	0.0120 (4)	0.0201 (4)
Sb2	0.03311 (11)	0.03102 (11)	0.03265 (11)	0.01310 (8)	0.00899 (8)	0.01088 (9)
Cl7	0.0387 (4)	0.0537 (5)	0.0463 (5)	0.0207 (4)	0.0039 (3)	0.0133 (4)
Cl9	0.0555 (5)	0.0718 (6)	0.0403 (4)	0.0266 (4)	0.0207 (4)	0.0195 (4)
Cl8	0.0743 (6)	0.0327 (4)	0.0724 (6)	0.0173 (4)	0.0249 (5)	0.0198 (4)
Cl5	0.0680 (6)	0.0411 (5)	0.0661 (6)	0.0207 (4)	0.0095 (5)	0.0252 (4)
Cl6	0.0632 (6)	0.0692 (6)	0.0527 (5)	0.0359 (5)	0.0274 (4)	0.0295 (5)
C10	0.0378 (17)	0.0436 (18)	0.050 (2)	0.0115 (14)	0.0189 (15)	0.0174 (16)
C14	0.049 (2)	0.045 (2)	0.054 (2)	0.0113 (16)	0.0148 (17)	0.0098 (17)
N2	0.0512 (18)	0.062 (2)	0.074 (2)	0.0242 (16)	0.0188 (17)	0.0363 (19)
C12	0.060 (2)	0.066 (3)	0.051 (2)	0.021 (2)	0.0104 (19)	0.024 (2)
C11	0.058 (2)	0.0444 (19)	0.048 (2)	0.0174 (17)	0.0160 (17)	0.0134 (17)
C13	0.062 (2)	0.045 (2)	0.084 (3)	0.0245 (19)	0.032 (2)	0.025 (2)
O2	0.086 (2)	0.097 (2)	0.0539 (18)	0.0350 (18)	0.0098 (16)	0.0284 (18)
C9	0.049 (2)	0.064 (2)	0.054 (2)	0.0180 (18)	0.0191 (18)	0.029 (2)
C8	0.115 (4)	0.073 (3)	0.086 (3)	0.058 (3)	0.019 (3)	0.029 (3)
C18	0.052 (2)	0.050 (2)	0.063 (2)	0.0253 (17)	0.0139 (18)	0.0182 (19)
N3	0.0535 (19)	0.059 (2)	0.0435 (17)	0.0063 (15)	0.0064 (14)	0.0091 (15)
C17	0.0345 (16)	0.0369 (17)	0.0491 (19)	0.0089 (13)	0.0141 (14)	0.0118 (15)
C16	0.043 (2)	0.062 (2)	0.054 (2)	0.0087 (18)	0.0123 (17)	0.011 (2)
C21	0.057 (2)	0.056 (2)	0.060 (2)	0.0328 (18)	0.0253 (19)	0.0211 (19)
C15	0.084 (3)	0.105 (4)	0.068 (3)	0.033 (3)	−0.005 (3)	0.028 (3)
C20	0.055 (2)	0.072 (3)	0.062 (3)	0.030 (2)	0.0186 (19)	0.034 (2)
O3	0.082 (2)	0.0704 (19)	0.0608 (18)	0.0244 (16)	0.0179 (15)	−0.0077 (15)
C19	0.081 (3)	0.046 (2)	0.057 (2)	0.026 (2)	0.020 (2)	0.0038 (19)

Geometric parameters (Å, º) top

O1—C2	1.215 (4)	C14—C13	1.350 (5)
N1—C6	1.327 (4)	C14—H14A	0.9300
N1—C5	1.329 (5)	N2—C12	1.316 (5)
N1—H1D	0.8600	N2—C13	1.325 (5)
C3—C7	1.374 (4)	N2—H2A	0.8600
C3—C4	1.381 (4)	C12—C11	1.367 (5)
C3—C2	1.502 (5)	C12—H12A	0.9300
C6—C7	1.348 (5)	C11—H11A	0.9300
C6—H6A	0.9300	C13—H13A	0.9300
C4—C5	1.345 (5)	O2—C9	1.200 (4)
C4—H4A	0.9300	C9—C8	1.464 (5)
C7—H7A	0.9300	C8—H8A	0.9600
C5—H5A	0.9300	C8—H8B	0.9600
C2—C1	1.476 (5)	C8—H8C	0.9600
C1—H1A	0.9600	C18—C19	1.354 (5)
C1—H1B	0.9600	C18—C17	1.370 (4)
C1—H1C	0.9600	C18—H18A	0.9300
Sb1—Cl4	2.4036 (9)	N3—C20	1.320 (5)
Sb1—Cl3	2.4107 (10)	N3—C19	1.320 (5)
Sb1—Cl2	2.4113 (14)	N3—H3A	0.8600
Sb1—Cl1	2.9359 (12)	C17—C21	1.374 (5)
Sb1—Cl5	3.0214 (12)	C17—C16	1.514 (5)
Sb1—Cl6ⁱ	3.1275 (12)	C16—O3	1.194 (4)
Sb2—Cl7	2.3516 (12)	C16—C15	1.473 (6)
Sb2—Cl8	2.4459 (10)	C21—C20	1.367 (5)
Sb2—Cl9	2.4498 (10)	C21—H21A	0.9300
Sb2—Cl5	2.8352 (11)	C15—H15A	0.9600
Sb2—Cl6	2.8937 (11)	C15—H15B	0.9600
C10—C14	1.373 (4)	C15—H15C	0.9600
C10—C11	1.378 (5)	C20—H20A	0.9300
C10—C9	1.511 (5)	C19—H19A	0.9300

C6—N1—C5	121.5 (3)	C12—N2—H2A	118.7
C6—N1—H1D	119.2	C13—N2—H2A	118.7
C5—N1—H1D	119.2	N2—C12—C11	119.7 (4)
C7—C3—C4	119.3 (3)	N2—C12—H12A	120.1
C7—C3—C2	118.9 (3)	C11—C12—H12A	120.1
C4—C3—C2	121.8 (3)	C12—C11—C10	119.3 (3)
N1—C6—C7	121.0 (3)	C12—C11—H11A	120.3
N1—C6—H6A	119.5	C10—C11—H11A	120.3
C7—C6—H6A	119.5	N2—C13—C14	119.8 (3)
C5—C4—C3	119.5 (3)	N2—C13—H13A	120.1
C5—C4—H4A	120.2	C14—C13—H13A	120.1
C3—C4—H4A	120.2	O2—C9—C8	122.4 (4)
C6—C7—C3	118.6 (3)	O2—C9—C10	117.8 (4)
C6—C7—H7A	120.7	C8—C9—C10	119.7 (3)
C3—C7—H7A	120.7	C9—C8—H8A	109.5
N1—C5—C4	120.0 (3)	C9—C8—H8B	109.5
N1—C5—H5A	120.0	H8A—C8—H8B	109.5
C4—C5—H5A	120.0	C9—C8—H8C	109.5
O1—C2—C1	121.9 (4)	H8A—C8—H8C	109.5
O1—C2—C3	119.5 (3)	H8B—C8—H8C	109.5
C1—C2—C3	118.6 (3)	C19—C18—C17	119.5 (4)
Cl4—Sb1—Cl3	92.15 (4)	C19—C18—H18A	120.2
Cl4—Sb1—Cl2	89.42 (5)	C17—C18—H18A	120.2
Cl3—Sb1—Cl2	90.96 (4)	C20—N3—C19	122.4 (3)
C2—C1—H1A	109.5	C20—N3—H3A	118.8
C2—C1—H1B	109.5	C19—N3—H3A	118.8
H1A—C1—H1B	109.5	C18—C17—C21	118.4 (3)
C2—C1—H1C	109.5	C18—C17—C16	122.7 (3)
H1A—C1—H1C	109.5	C21—C17—C16	118.8 (3)
H1B—C1—H1C	109.5	O3—C16—C15	122.5 (4)
Cl7—Sb2—Cl8	90.05 (5)	O3—C16—C17	118.7 (4)
Cl7—Sb2—Cl9	87.97 (4)	C15—C16—C17	118.8 (4)
Cl8—Sb2—Cl9	90.76 (4)	C20—C21—C17	120.2 (3)
Cl7—Sb2—Cl5	86.83 (5)	C20—C21—H21A	119.9
Cl8—Sb2—Cl5	174.29 (3)	C17—C21—H21A	119.9
Cl9—Sb2—Cl5	93.90 (4)	C16—C15—H15A	109.5
Cl7—Sb2—Cl6	83.07 (4)	C16—C15—H15B	109.5
Cl8—Sb2—Cl6	89.72 (4)	H15A—C15—H15B	109.5
Cl9—Sb2—Cl6	171.03 (3)	C16—C15—H15C	109.5
Cl5—Sb2—Cl6	85.17 (4)	H15A—C15—H15C	109.5
C14—C10—C11	118.7 (3)	H15B—C15—H15C	109.5
C14—C10—C9	118.9 (3)	N3—C20—C21	119.0 (4)
C11—C10—C9	122.4 (3)	N3—C20—H20A	120.5
C13—C14—C10	119.9 (4)	C21—C20—H20A	120.5
C13—C14—H14A	120.0	N3—C19—C18	120.4 (3)
C10—C14—H14A	120.0	N3—C19—H19A	119.8
C12—N2—C13	122.5 (3)	C18—C19—H19A	119.8

C5—N1—C6—C7	1.5 (6)	C12—N2—C13—C14	0.3 (6)
C7—C3—C4—C5	0.7 (5)	C10—C14—C13—N2	0.9 (6)
C2—C3—C4—C5	−176.9 (3)	C14—C10—C9—O2	1.7 (5)
N1—C6—C7—C3	−2.4 (6)	C11—C10—C9—O2	179.5 (3)
C4—C3—C7—C6	1.3 (5)	C14—C10—C9—C8	−177.2 (4)
C2—C3—C7—C6	179.0 (3)	C11—C10—C9—C8	0.6 (5)
C6—N1—C5—C4	0.6 (6)	C19—C18—C17—C21	−1.1 (5)
C3—C4—C5—N1	−1.7 (6)	C19—C18—C17—C16	178.2 (4)
C7—C3—C2—O1	−16.1 (5)	C18—C17—C16—O3	175.1 (4)
C4—C3—C2—O1	161.5 (3)	C21—C17—C16—O3	−5.6 (5)
C7—C3—C2—C1	165.5 (4)	C18—C17—C16—C15	−4.1 (5)
C4—C3—C2—C1	−16.9 (5)	C21—C17—C16—C15	175.1 (4)
C11—C10—C14—C13	−1.0 (5)	C18—C17—C21—C20	1.6 (5)
C9—C10—C14—C13	176.9 (3)	C16—C17—C21—C20	−177.7 (3)
C13—N2—C12—C11	−1.4 (6)	C19—N3—C20—C21	−1.3 (6)
N2—C12—C11—C10	1.2 (6)	C17—C21—C20—N3	−0.4 (6)
C14—C10—C11—C12	0.0 (5)	C20—N3—C19—C18	1.9 (6)
C9—C10—C11—C12	−177.8 (3)	C17—C18—C19—N3	−0.6 (6)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl6	0.86	2.30	3.148 (3)	170
N1—H1D···Cl1ⁱⁱ	0.86	2.20	3.056 (3)	174
N3—H3A···Cl5ⁱⁱⁱ	0.86	2.35	3.198 (3)	168
C1—H1A···O2^iv	0.96	2.60	3.506 (5)	158
C5—H5A···Cl8^v	0.93	2.78	3.585 (4)	146
C13—H13A···Cl1ⁱ	0.93	2.76	3.661 (4)	162
C19—H19A···Cl7ⁱⁱⁱ	0.93	2.67	3.449 (4)	141
C21—H21A···O1ⁱⁱⁱ	0.93	2.42	3.349 (4)	177

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

Experimental details

Crystal data
Chemical formula	(C₇H₈NO)₆[Sb₄Cl₁₈]
M_r	1857.96
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.0589 (18), 13.838 (3), 15.128 (3)
α, β, γ (°)	108.29 (3), 98.00 (3), 107.10 (3)
V (Å³)	1664.1 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.37
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.430, 0.622
No. of measured, independent and observed [I > 2σ(I)] reflections	17638, 7613, 6371
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.070, 1.04
No. of reflections	7613
No. of parameters	343
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.38

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Sb1—Cl4	2.4036 (9)	Sb2—Cl7	2.3516 (12)
Sb1—Cl3	2.4107 (10)	Sb2—Cl8	2.4459 (10)
Sb1—Cl2	2.4113 (14)	Sb2—Cl9	2.4498 (10)
Sb1—Cl1	2.9359 (12)	Sb2—Cl5	2.8352 (11)
Sb1—Cl5	3.0214 (12)	Sb2—Cl6	2.8937 (11)
Sb1—Cl6ⁱ	3.1275 (12)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl6	0.86	2.30	3.148 (3)	170
N1—H1D···Cl1ⁱⁱ	0.86	2.20	3.056 (3)	174
N3—H3A···Cl5ⁱⁱⁱ	0.86	2.35	3.198 (3)	168
C1—H1A···O2^iv	0.96	2.60	3.506 (5)	158
C5—H5A···Cl8^v	0.93	2.78	3.585 (4)	146
C13—H13A···Cl1ⁱ	0.93	2.76	3.661 (4)	162
C19—H19A···Cl7ⁱⁱⁱ	0.93	2.67	3.449 (4)	141
C21—H21A···O1ⁱⁱⁱ	0.93	2.42	3.349 (4)	177

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

Acknowledgements

The author is grateful to the starter fund of Southeast University for financial support to purchase the X-ray diffractometer.

References

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