Chloridobis{2-[(dimethyl­amino)­meth­yl]phen­yl}anti­mony(III)

Olaru, M.; Roşca, S.; Raţ, C.I.; Silvestru, C.

doi:10.1107/S1600536809041890

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages m1383-m1384

https://doi.org/10.1107/S1600536809041890

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Chloridobis{2-[(dimethylamino)methyl]phenyl}antimony(III)

Marian Olaru,^a Sorin Roşca,^a Ciprian I. Raţ ^a ^* and Cristian Silvestru ^a

^aUniversitatea Babeş-Bolyai, Facultatea de Chimie şi Inginerie Chimicã, 11 Arany Janos, 400028 Cluj-Napoca, Romania
^*Correspondence e-mail: crat@chem.ubbcluj.ro

(Received 1 October 2009; accepted 13 October 2009; online 17 October 2009)

In the title compound, [Sb(C₉H₁₂N)₂Cl], the Sb atom adopts a Ψ-trigonal-bipyramidal geometry. The two 2-[(dimethylamino)methyl]phenyl ligands are coordinated asymmetrically to the Sb atom. The carbon atoms of one of the ligands are disordered over sets of sites with equal occupancy, resulting in two conformational isomers in the crystal. The Sb—C and Sb—N distances in the ordered ligand are: 2.153 (4) and 3.326 (5) Å, respectively. The corresponding distances in the disordered ligand are: 2.103 (5)/2.188 (5) and 2.454 (3) Å, respectively. The structure displays intramolecular C—H⋯Cl hydrogen bonding.

Related literature

For the structure of the perdeuterobenzene solvate of the title compound, see: Carmalt et al. (1997 ). For antimony(III) compounds with 2-[(dimethylamino)methyl]phenyl substituents, see: Kamepalli et al. (1996 ); Tokunaga et al. (2000a ,b ); Breunig et al. (2003 ); Opris et al. (2003 , 2004 , 2009 ); Sharma et al. (2004 ).

Experimental

Crystal data

[Sb(C₉H₁₂N)₂Cl]
M_r = 425.60
Triclinic, $[P \overline 1]$
a = 9.289 (7) Å
b = 9.367 (7) Å
c = 12.888 (10) Å
α = 98.073 (13)°
β = 103.611 (13)°
γ = 116.819 (12)°
V = 932.6 (13) Å³
Z = 2
Mo Kα radiation
μ = 1.62 mm⁻¹
T = 297 K
0.33 × 0.31 × 0.27 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.617, T_max = 0.669
10065 measured reflections
3801 independent reflections
3530 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.078
S = 1.13
3801 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cl1	0.93	2.65	3.291 (7)	127
C6A—H6A⋯Cl1	0.93	2.74	3.353 (7)	125

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999 ); molecular graphics: DIAMOND (Brandenburg, 2009 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809041890/pv2214sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041890/pv2214Isup2.hkl

checkCIF report

Comment top

The molecular structure of the perdeuterated benzene solvate of the title compound, (I).C₆D₆, was first determined by Carmalt et al. (1997). The existence of different enantiomers in the crystal structures of bis[2-(dimethylaminomethyl)phenyl]organoantimony(III) bromide and iodide has been reported (Opris et al., 2003).

In the structure of (I), there are two dimethylaminomethylphenyl ligands that are asymmetrically coordinated to the Sb atom; the Sb atom adopts a Ψ-trigonal-bipyramidal geometry. The ligand containing nitrogen atom N1 was found to be disordered over two positions with s.o.f. of 0.501 (6) (Fig. 1), and 0.499 (6) (Fig. 2) thus resulting in two conformational isomers. Intramolecular hydrogen bonds are present between the chlorine atom and hydrogen atom in position 6 of the organic substituent containing the N1 atom (Table 1).

Bond distances and bond angles in (I) are similar to those reported for the perdeuteraded benzene solvate of the title compound (Carmalt et al., 1997).

Related literature top

For the structure of the perdeuterobenzene solvate of the title compound, see: Carmalt et al. (1997). For antimony(III) compounds with 2-[(dimethylamino)methyl]phenyl substituents, see: Kamepalli et al. (1996); Tokunaga et al. (2000a,b); Breunig et al. (2003); Opris et al. (2003, 2004, 2009); Sharma et al. (2004).

Experimental top

The title compound was prepared according to a previously described method (Carmalt et al., 1997). Colourless crystals were obtained from a solution in chloroform by slow evaporation of the solvent.

Structure description top

?···..

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. Graphical representation of the molecular structure of R_N1,S_N2-1. Hydrogen atoms were omitted for clarity. Displacement ellipsoids are drawn at 25% probability.
	Fig. 2. Graphical representation of the molecular structure of S_N1,S_N2-1. Hydrogen atoms were omitted for clarity. Displacement ellipsoids are drawn at 25% probability.

Chloridobis{2-[(dimethylamino)methyl]phenyl}antimony(III) top

Crystal data top

[Sb(C₉H₁₂N)₂Cl]	Z = 2
M_r = 425.60	F(000) = 428
Triclinic, P1	D_x = 1.516 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.289 (7) Å	Cell parameters from 3906 reflections
b = 9.367 (7) Å	θ = 2.5–24.4°
c = 12.888 (10) Å	µ = 1.62 mm⁻¹
α = 98.073 (13)°	T = 297 K
β = 103.611 (13)°	Blocks, colourless
γ = 116.819 (12)°	0.33 × 0.31 × 0.27 mm
V = 932.6 (13) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3801 independent reflections
Radiation source: fine-focus sealed tube	3530 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 26.4°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
T_min = 0.617, T_max = 0.669	k = −11→11
10065 measured reflections	l = −16→16

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.035P)² + 0.2481P] where P = (F_o² + 2F_c²)/3
3801 reflections	(Δ/σ)_max = 0.001
263 parameters	Δρ_max = 0.78 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Sb(C₉H₁₂N)₂Cl]	γ = 116.819 (12)°
M_r = 425.60	V = 932.6 (13) Å³
Triclinic, P1	Z = 2
a = 9.289 (7) Å	Mo Kα radiation
b = 9.367 (7) Å	µ = 1.62 mm⁻¹
c = 12.888 (10) Å	T = 297 K
α = 98.073 (13)°	0.33 × 0.31 × 0.27 mm
β = 103.611 (13)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3801 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3530 reflections with I > 2σ(I)
T_min = 0.617, T_max = 0.669	R_int = 0.027
10065 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.13	Δρ_max = 0.78 e Å⁻³
3801 reflections	Δρ_min = −0.45 e Å⁻³
263 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
C1	0.7468 (8)	0.4324 (9)	0.6493 (5)	0.047 (6)	0.501 (6)
C2	0.6306 (6)	0.2626 (10)	0.6213 (6)	0.048 (2)	0.501 (6)
C3	0.6832 (9)	0.1477 (7)	0.5996 (7)	0.065 (3)	0.501 (6)
H3	0.6055	0.034	0.5808	0.078*	0.501 (6)
C4	0.8521 (10)	0.2026 (8)	0.6058 (7)	0.065 (4)	0.501 (6)
H4	0.8873	0.1257	0.5913	0.078*	0.501 (6)
C5	0.9683 (8)	0.3724 (8)	0.6339 (7)	0.067 (2)	0.501 (6)
H5	1.0813	0.4091	0.6381	0.081*	0.501 (6)
C6	0.9156 (8)	0.4873 (6)	0.6556 (6)	0.058 (2)	0.501 (6)
H6	0.9934	0.601	0.6744	0.069*	0.501 (6)
C7	0.4477 (9)	0.2067 (9)	0.6097 (6)	0.055 (2)	0.501 (6)
H7A	0.3864	0.2057	0.5372	0.065*	0.501 (6)
H7B	0.3913	0.0952	0.6181	0.065*	0.501 (6)
C8	0.2676 (10)	0.3037 (11)	0.6608 (8)	0.074 (3)	0.501 (6)
H8A	0.2416	0.3183	0.5877	0.111*	0.501 (6)
H8B	0.2619	0.3844	0.712	0.111*	0.501 (6)
H8C	0.1859	0.1933	0.6589	0.111*	0.501 (6)
C9	0.4842 (13)	0.2998 (11)	0.8043 (7)	0.069 (3)	0.501 (6)
H9A	0.391	0.1953	0.8018	0.104*	0.501 (6)
H9B	0.495	0.3882	0.859	0.104*	0.501 (6)
H9C	0.5886	0.2963	0.8238	0.104*	0.501 (6)
C1A	0.7522 (8)	0.4295 (8)	0.6416 (5)	0.042 (5)	0.499 (6)
C2A	0.6821 (9)	0.2798 (10)	0.6685 (5)	0.048 (2)	0.499 (6)
C3A	0.7282 (10)	0.1620 (8)	0.6387 (7)	0.056 (3)	0.499 (6)
H3A	0.6813	0.0618	0.6568	0.067*	0.499 (6)
C4A	0.8444 (10)	0.1940 (7)	0.5819 (7)	0.068 (4)	0.499 (6)
H4A	0.8752	0.1152	0.562	0.081*	0.499 (6)
C5A	0.9145 (7)	0.3438 (8)	0.5549 (6)	0.060 (2)	0.499 (6)
H5A	0.9922	0.3652	0.5169	0.072*	0.499 (6)
C6A	0.8684 (7)	0.4615 (6)	0.5847 (6)	0.0510 (19)	0.499 (6)
H6A	0.9153	0.5617	0.5667	0.061*	0.499 (6)
C7A	0.5589 (10)	0.2447 (9)	0.7299 (7)	0.057 (2)	0.499 (6)
H7A1	0.6209	0.2862	0.8093	0.068*	0.499 (6)
H7A2	0.4835	0.1251	0.7115	0.068*	0.499 (6)
C8A	0.3298 (10)	0.2411 (10)	0.5935 (7)	0.064 (2)	0.499 (6)
H8A1	0.2438	0.1354	0.5954	0.096*	0.499 (6)
H8A2	0.3839	0.2235	0.5421	0.096*	0.499 (6)
H8A3	0.2773	0.3044	0.5702	0.096*	0.499 (6)
C9A	0.3800 (12)	0.3423 (11)	0.7886 (7)	0.070 (3)	0.499 (6)
H9A1	0.3175	0.3997	0.7735	0.105*	0.499 (6)
H9A2	0.4715	0.4034	0.8587	0.105*	0.499 (6)
H9A3	0.3043	0.2327	0.7915	0.105*	0.499 (6)
C10	0.7798 (4)	0.6853 (4)	0.8586 (3)	0.0469 (8)
C11	0.7516 (5)	0.7975 (4)	0.9215 (3)	0.0555 (9)
C12	0.8347 (6)	0.8557 (5)	1.0355 (3)	0.0677 (11)
H12	0.818	0.9321	1.078	0.081*
C13	0.9393 (6)	0.8043 (6)	1.0865 (3)	0.0768 (14)
H13	0.9908	0.8421	1.1635	0.092*
C14	0.9696 (5)	0.6964 (6)	1.0246 (4)	0.0748 (13)
H14	1.0441	0.6632	1.0595	0.09*
C15	0.8894 (5)	0.6365 (5)	0.9100 (3)	0.0606 (10)
H15	0.9101	0.5631	0.8681	0.073*
C16	0.6406 (6)	0.8609 (5)	0.8671 (4)	0.0683 (11)
H16A	0.6536	0.9523	0.9217	0.082*
H16B	0.6789	0.9041	0.8086	0.082*
C17	0.3876 (7)	0.6916 (8)	0.9063 (5)	0.1067 (18)
H17A	0.4441	0.6456	0.9508	0.16*
H17B	0.2676	0.6111	0.8728	0.16*
H17C	0.4023	0.7903	0.9526	0.16*
C18	0.3679 (9)	0.7882 (9)	0.7445 (6)	0.133 (3)
H18A	0.3749	0.8867	0.785	0.199*
H18B	0.25	0.7014	0.7116	0.199*
H18C	0.417	0.8127	0.687	0.199*
N1	0.4519 (4)	0.3284 (4)	0.6993 (2)	0.0517 (7)
N2	0.4613 (5)	0.7338 (5)	0.8199 (3)	0.0714 (9)
Sb1	0.65485 (3)	0.59640 (3)	0.680735 (17)	0.04391 (10)
Cl1	0.92046 (15)	0.84267 (12)	0.66663 (9)	0.0677 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.044 (12)	0.053 (13)	0.038 (9)	0.024 (11)	0.009 (9)	0.004 (8)
C2	0.056 (5)	0.042 (4)	0.040 (5)	0.026 (4)	0.009 (4)	0.003 (4)
C3	0.093 (8)	0.052 (6)	0.058 (7)	0.043 (6)	0.023 (6)	0.015 (4)
C4	0.097 (12)	0.063 (9)	0.057 (6)	0.061 (9)	0.020 (6)	0.013 (5)
C5	0.070 (6)	0.077 (6)	0.068 (6)	0.045 (5)	0.031 (5)	0.016 (5)
C6	0.062 (5)	0.061 (5)	0.059 (5)	0.035 (4)	0.026 (5)	0.022 (4)
C7	0.054 (5)	0.042 (4)	0.052 (4)	0.018 (3)	0.011 (3)	0.005 (3)
C8	0.045 (4)	0.063 (5)	0.090 (7)	0.015 (4)	0.018 (4)	0.008 (5)
C9	0.085 (7)	0.057 (5)	0.057 (5)	0.026 (5)	0.028 (5)	0.021 (4)
C1A	0.056 (14)	0.038 (11)	0.038 (9)	0.028 (10)	0.016 (9)	0.013 (7)
C2A	0.045 (5)	0.045 (5)	0.048 (6)	0.021 (4)	0.008 (4)	0.012 (4)
C3A	0.054 (5)	0.036 (4)	0.068 (8)	0.021 (4)	0.011 (5)	0.011 (4)
C4A	0.050 (8)	0.069 (10)	0.072 (7)	0.034 (7)	0.006 (5)	−0.003 (5)
C5A	0.047 (4)	0.057 (5)	0.070 (6)	0.024 (4)	0.022 (4)	0.005 (4)
C6A	0.045 (4)	0.053 (4)	0.053 (5)	0.024 (4)	0.013 (4)	0.014 (4)
C7A	0.060 (5)	0.049 (4)	0.064 (5)	0.025 (4)	0.024 (4)	0.025 (4)
C8A	0.057 (5)	0.048 (4)	0.066 (5)	0.016 (4)	0.014 (4)	0.004 (4)
C9A	0.076 (6)	0.070 (6)	0.063 (5)	0.028 (5)	0.040 (5)	0.020 (4)
C10	0.0482 (18)	0.0412 (18)	0.0354 (17)	0.0122 (15)	0.0117 (14)	0.0073 (14)
C11	0.061 (2)	0.0398 (18)	0.0454 (19)	0.0094 (17)	0.0221 (17)	0.0055 (15)
C12	0.066 (3)	0.055 (2)	0.052 (2)	0.008 (2)	0.025 (2)	0.0036 (19)
C13	0.067 (3)	0.081 (3)	0.0329 (19)	0.005 (2)	0.0127 (19)	−0.001 (2)
C14	0.060 (3)	0.086 (3)	0.056 (3)	0.025 (2)	0.004 (2)	0.022 (2)
C15	0.056 (2)	0.066 (2)	0.046 (2)	0.025 (2)	0.0093 (17)	0.0096 (18)
C16	0.101 (3)	0.048 (2)	0.066 (3)	0.041 (2)	0.040 (2)	0.0163 (19)
C17	0.100 (4)	0.128 (5)	0.122 (5)	0.066 (4)	0.067 (4)	0.039 (4)
C18	0.146 (6)	0.149 (6)	0.161 (7)	0.114 (5)	0.044 (5)	0.077 (5)
N1	0.0538 (17)	0.0515 (17)	0.0482 (17)	0.0244 (15)	0.0207 (14)	0.0115 (14)
N2	0.078 (2)	0.076 (2)	0.083 (3)	0.050 (2)	0.036 (2)	0.034 (2)
Sb1	0.05461 (16)	0.04224 (14)	0.03608 (14)	0.02685 (12)	0.01251 (10)	0.01049 (9)
Cl1	0.0829 (7)	0.0465 (5)	0.0674 (6)	0.0227 (5)	0.0340 (6)	0.0182 (5)

Geometric parameters (Å, º) top

C1—C2	1.39	C7A—H7A1	0.97
C1—C6	1.39	C7A—H7A2	0.97
C1—Sb1	2.103 (5)	C8A—N1	1.391 (8)
C2—C3	1.39	C8A—H8A1	0.96
C2—C7	1.496 (9)	C8A—H8A2	0.96
C3—C4	1.39	C8A—H8A3	0.96
C3—H3	0.93	C9A—N1	1.479 (9)
C4—C5	1.39	C9A—H9A1	0.96
C4—H4	0.93	C9A—H9A2	0.96
C5—C6	1.39	C9A—H9A3	0.96
C5—H5	0.93	C10—C15	1.369 (5)
C6—H6	0.93	C10—C11	1.393 (5)
C7—N1	1.484 (8)	C10—Sb1	2.153 (4)
C7—H7A	0.97	C11—C12	1.383 (5)
C7—H7B	0.97	C11—C16	1.496 (6)
C8—N1	1.563 (9)	C12—C13	1.348 (7)
C8—H8A	0.96	C12—H12	0.93
C8—H8B	0.96	C13—C14	1.368 (7)
C8—H8C	0.96	C13—H13	0.93
C9—N1	1.406 (8)	C14—C15	1.387 (6)
C9—H9A	0.96	C14—H14	0.93
C9—H9B	0.96	C15—H15	0.93
C9—H9C	0.96	C16—N2	1.446 (6)
C1A—C2A	1.39	C16—H16A	0.97
C1A—C6A	1.39	C16—H16B	0.97
C1A—Sb1	2.188 (5)	C17—N2	1.451 (6)
C2A—C3A	1.39	C17—H17A	0.96
C2A—C7A	1.484 (9)	C17—H17B	0.96
C3A—C4A	1.39	C17—H17C	0.96
C3A—H3A	0.93	C18—N2	1.448 (6)
C4A—C5A	1.39	C18—H18A	0.96
C4A—H4A	0.93	C18—H18B	0.96
C5A—C6A	1.39	C18—H18C	0.96
C5A—H5A	0.93	N1—Sb1	2.454 (3)
C6A—H6A	0.93	N2—Sb1	3.326 (5)
C7A—N1	1.537 (8)	Sb1—Cl1	2.5759 (18)

C2—C1—C6	120	C12—C11—C10	118.7 (4)
C2—C1—Sb1	117.2 (4)	C12—C11—C16	120.2 (4)
C6—C1—Sb1	122.8 (4)	C10—C11—C16	121.0 (3)
C3—C2—C1	120	C13—C12—C11	121.5 (4)
C3—C2—C7	121.1 (6)	C13—C12—H12	119.2
C1—C2—C7	118.9 (6)	C11—C12—H12	119.2
C4—C3—C2	120	C12—C13—C14	119.8 (4)
C4—C3—H3	120	C12—C13—H13	120.1
C2—C3—H3	120	C14—C13—H13	120.1
C5—C4—C3	120	C13—C14—C15	120.2 (4)
C5—C4—H4	120	C13—C14—H14	119.9
C3—C4—H4	120	C15—C14—H14	119.9
C6—C5—C4	120	C10—C15—C14	120.0 (4)
C6—C5—H5	120	C10—C15—H15	120
C4—C5—H5	120	C14—C15—H15	120
C5—C6—C1	120	N2—C16—C11	112.9 (3)
C5—C6—H6	120	N2—C16—H16A	109
C1—C6—H6	120	C11—C16—H16A	109
N1—C7—C2	106.2 (5)	N2—C16—H16B	109
N1—C7—H7A	110.5	C11—C16—H16B	109
C2—C7—H7A	110.5	H16A—C16—H16B	107.8
N1—C7—H7B	110.5	N2—C17—H17A	109.5
C2—C7—H7B	110.5	N2—C17—H17B	109.5
H7A—C7—H7B	108.7	H17A—C17—H17B	109.5
N1—C8—H8A	109.5	N2—C17—H17C	109.5
N1—C8—H8B	109.5	H17A—C17—H17C	109.5
N1—C8—H8C	109.5	H17B—C17—H17C	109.5
N1—C9—H9A	109.5	N2—C18—H18A	109.5
N1—C9—H9B	109.5	N2—C18—H18B	109.5
N1—C9—H9C	109.5	H18A—C18—H18B	109.5
C2A—C1A—C6A	120	N2—C18—H18C	109.5
C2A—C1A—Sb1	116.7 (4)	H18A—C18—H18C	109.5
C6A—C1A—Sb1	123.1 (4)	H18B—C18—H18C	109.5
C3A—C2A—C1A	120	C8A—N1—C9	137.0 (6)
C3A—C2A—C7A	119.5 (6)	C8A—N1—C9A	114.3 (6)
C1A—C2A—C7A	120.5 (6)	C9—N1—C9A	48.6 (5)
C2A—C3A—C4A	120	C8A—N1—C7	51.7 (5)
C2A—C3A—H3A	120	C9—N1—C7	114.1 (6)
C4A—C3A—H3A	120	C9A—N1—C7	143.2 (5)
C5A—C4A—C3A	120	C8A—N1—C7A	110.2 (5)
C5A—C4A—H4A	120	C9—N1—C7A	59.8 (5)
C3A—C4A—H4A	120	C9A—N1—C7A	107.8 (6)
C6A—C5A—C4A	120	C7—N1—C7A	61.0 (4)
C6A—C5A—H5A	120	C8A—N1—C8	54.1 (5)
C4A—C5A—H5A	120	C9—N1—C8	108.4 (6)
C5A—C6A—C1A	120	C9A—N1—C8	64.2 (6)
C5A—C6A—H6A	120	C7—N1—C8	104.2 (5)
C1A—C6A—H6A	120	C7A—N1—C8	145.7 (5)
C2A—C7A—N1	110.5 (5)	C8A—N1—Sb1	105.1 (4)
C2A—C7A—H7A1	109.5	C9—N1—Sb1	117.9 (4)
N1—C7A—H7A1	109.5	C9A—N1—Sb1	114.6 (4)
C2A—C7A—H7A2	109.5	C7—N1—Sb1	102.2 (3)
N1—C7A—H7A2	109.5	C7A—N1—Sb1	104.3 (3)
H7A1—C7A—H7A2	108.1	C8—N1—Sb1	109.2 (4)
N1—C8A—H8A1	109.5	C16—N2—C18	110.2 (4)
N1—C8A—H8A2	109.5	C16—N2—C17	111.2 (4)
H8A1—C8A—H8A2	109.5	C18—N2—C17	110.9 (5)
N1—C8A—H8A3	109.5	C1—Sb1—C10	96.9 (2)
H8A1—C8A—H8A3	109.5	C1—Sb1—C1A	2.6 (3)
H8A2—C8A—H8A3	109.5	C10—Sb1—C1A	98.77 (18)
N1—C9A—H9A1	109.5	C1—Sb1—N1	73.2 (2)
N1—C9A—H9A2	109.5	C10—Sb1—N1	89.75 (12)
H9A1—C9A—H9A2	109.5	C1A—Sb1—N1	75.0 (2)
N1—C9A—H9A3	109.5	C1—Sb1—Cl1	91.9 (2)
H9A1—C9A—H9A3	109.5	C10—Sb1—Cl1	87.61 (10)
H9A2—C9A—H9A3	109.5	C1A—Sb1—Cl1	90.3 (2)
C15—C10—C11	119.7 (3)	N1—Sb1—Cl1	164.43 (8)
C15—C10—Sb1	121.0 (3)	N2—Sb1—Cl1	110.65 (8)
C11—C10—Sb1	119.3 (3)

C6—C1—C2—C3	0	C11—C16—N2—C18	−165.1 (4)
Sb1—C1—C2—C3	180.0 (5)	C11—C16—N2—C17	71.6 (5)
C6—C1—C2—C7	−177.0 (7)	C2—C1—Sb1—C10	106.9 (4)
Sb1—C1—C2—C7	3.0 (7)	C6—C1—Sb1—C10	−73.1 (4)
C1—C2—C3—C4	0	C2—C1—Sb1—C1A	−114 (7)
C7—C2—C3—C4	177.0 (7)	C6—C1—Sb1—C1A	66 (7)
C2—C3—C4—C5	0	C2—C1—Sb1—N1	19.3 (4)
C3—C4—C5—C6	0	C6—C1—Sb1—N1	−160.7 (4)
C4—C5—C6—C1	0	C2—C1—Sb1—Cl1	−165.3 (4)
C2—C1—C6—C5	0	C6—C1—Sb1—Cl1	14.7 (4)
Sb1—C1—C6—C5	180.0 (5)	C15—C10—Sb1—C1	4.3 (4)
C3—C2—C7—N1	144.3 (5)	C11—C10—Sb1—C1	−177.3 (3)
C1—C2—C7—N1	−38.6 (8)	C15—C10—Sb1—C1A	2.6 (4)
C6A—C1A—C2A—C3A	0	C11—C10—Sb1—C1A	−179.0 (3)
Sb1—C1A—C2A—C3A	175.2 (4)	C15—C10—Sb1—N1	77.3 (3)
C6A—C1A—C2A—C7A	179.6 (7)	C11—C10—Sb1—N1	−104.3 (3)
Sb1—C1A—C2A—C7A	−5.2 (7)	C15—C10—Sb1—Cl1	−87.3 (3)
C1A—C2A—C3A—C4A	0	C11—C10—Sb1—Cl1	91.1 (3)
C7A—C2A—C3A—C4A	−179.6 (7)	C2A—C1A—Sb1—C1	33 (7)
C2A—C3A—C4A—C5A	0	C6A—C1A—Sb1—C1	−152 (7)
C3A—C4A—C5A—C6A	0	C2A—C1A—Sb1—C10	74.1 (3)
C4A—C5A—C6A—C1A	0	C6A—C1A—Sb1—C10	−110.8 (4)
C2A—C1A—C6A—C5A	0	C2A—C1A—Sb1—N1	−13.3 (3)
Sb1—C1A—C6A—C5A	−174.9 (5)	C6A—C1A—Sb1—N1	161.8 (4)
C3A—C2A—C7A—N1	−148.5 (4)	C2A—C1A—Sb1—Cl1	161.7 (3)
C1A—C2A—C7A—N1	31.9 (8)	C6A—C1A—Sb1—Cl1	−23.2 (4)
C15—C10—C11—C12	−0.6 (5)	C8A—N1—Sb1—C1	−90.6 (5)
Sb1—C10—C11—C12	−179.0 (3)	C9—N1—Sb1—C1	88.5 (6)
C15—C10—C11—C16	176.5 (4)	C9A—N1—Sb1—C1	143.0 (5)
Sb1—C10—C11—C16	−1.9 (5)	C7—N1—Sb1—C1	−37.4 (4)
C10—C11—C12—C13	−1.1 (6)	C7A—N1—Sb1—C1	25.4 (4)
C16—C11—C12—C13	−178.2 (4)	C8—N1—Sb1—C1	−147.3 (5)
C11—C12—C13—C14	2.2 (6)	C8A—N1—Sb1—C10	172.1 (4)
C12—C13—C14—C15	−1.7 (7)	C9—N1—Sb1—C10	−8.7 (5)
C11—C10—C15—C14	1.1 (6)	C9A—N1—Sb1—C10	45.8 (5)
Sb1—C10—C15—C14	179.5 (3)	C7—N1—Sb1—C10	−134.6 (4)
C13—C14—C15—C10	0.1 (6)	C7A—N1—Sb1—C10	−71.8 (4)
C12—C11—C16—N2	−113.5 (4)	C8—N1—Sb1—C10	115.5 (4)
C10—C11—C16—N2	69.5 (5)	C8A—N1—Sb1—C1A	−88.7 (4)
C2—C7—N1—C8A	147.4 (8)	C9—N1—Sb1—C1A	90.4 (6)
C2—C7—N1—C9	−80.7 (7)	C9A—N1—Sb1—C1A	145.0 (5)
C2—C7—N1—C9A	−133.0 (9)	C7—N1—Sb1—C1A	−35.5 (4)
C2—C7—N1—C7A	−52.1 (6)	C7A—N1—Sb1—C1A	27.3 (4)
C2—C7—N1—C8	161.3 (6)	C8—N1—Sb1—C1A	−145.4 (4)
C2—C7—N1—Sb1	47.7 (6)	C8A—N1—Sb1—Cl1	−107.7 (5)
C2A—C7A—N1—C8A	74.7 (7)	C9—N1—Sb1—Cl1	71.4 (6)
C2A—C7A—N1—C9	−151.9 (8)	C9A—N1—Sb1—Cl1	126.0 (5)
C2A—C7A—N1—C9A	−159.9 (6)	C7—N1—Sb1—Cl1	−54.5 (5)
C2A—C7A—N1—C7	58.5 (6)	C7A—N1—Sb1—Cl1	8.3 (5)
C2A—C7A—N1—C8	130.0 (9)	C8—N1—Sb1—Cl1	−164.4 (4)
C2A—C7A—N1—Sb1	−37.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cl1	0.93	2.65	3.291 (7)	127
C6A—H6A···Cl1	0.93	2.74	3.353 (7)	125

Experimental details

Crystal data
Chemical formula	[Sb(C₉H₁₂N)₂Cl]
M_r	425.60
Crystal system, space group	Triclinic, P1
Temperature (K)	297
a, b, c (Å)	9.289 (7), 9.367 (7), 12.888 (10)
α, β, γ (°)	98.073 (13), 103.611 (13), 116.819 (12)
V (Å³)	932.6 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.62
Crystal size (mm)	0.33 × 0.31 × 0.27

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.617, 0.669
No. of measured, independent and observed [I > 2σ(I)] reflections	10065, 3801, 3530
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.078, 1.13
No. of reflections	3801
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.45

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999), DIAMOND (Brandenburg, 2009), publCIF (Westrip, 2009).

Selected geometric parameters (Å, º) top

C1—Sb1	2.103 (5)	N2—Sb1	3.326 (5)
C1A—Sb1	2.188 (5)	Sb1—Cl1	2.5759 (18)
N1—Sb1	2.454 (3)

C1—Sb1—C1A	2.6 (3)	C1—Sb1—Cl1	91.9 (2)
C10—Sb1—C1A	98.77 (18)	C10—Sb1—Cl1	87.61 (10)
C1—Sb1—N1	73.2 (2)	C1A—Sb1—Cl1	90.3 (2)
C10—Sb1—N1	89.75 (12)	N1—Sb1—Cl1	164.43 (8)
C1A—Sb1—N1	75.0 (2)	N2—Sb1—Cl1	110.65 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cl1	0.93	2.65	3.291 (7)	127
C6A—H6A···Cl1	0.93	2.74	3.353 (7)	125

Acknowledgements

We thank Dr Albert Soran for the crystal selection and measurement and Dr Richard A. Varga for helpful suggestions regarding the disorder refinement. This work was supported by the National University Research Council (CNCSIS) of Romania (research project PNII-ID 2052/2009). MO thanks Babeş-Bolyai University for a research fellowship (14/01.10.2008).

References

Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Breunig, H. J., Ghesner, I., Ghesner, M. E. & Lork, E. (2003). Inorg. Chem. 42, 1751–1757. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2000). SMART and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA. Google Scholar
Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Carmalt, C. J., Cowley, A. H., Culp, R. D., Jones, R. A., Kamepalli, S. & Norman, N. C. (1997). Inorg. Chem. 36, 2770–2776. CSD CrossRef PubMed CAS Web of Science Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Kamepalli, S., Carmalt, C. J., Culp, R. D., Cowley, A. H., Jones, R. A. & Norman, N. C. (1996). Inorg. Chem. 35, 6179–6183. CSD CrossRef CAS Web of Science Google Scholar
Opris, L. M., Preda, A. M., Varga, R. A., Breunig, H. J. & Silvestru, C. (2009). Eur. J. Inorg. Chem. pp. 1187–1193. Web of Science CSD CrossRef Google Scholar
Opris, L. M., Silvestru, A., Silvestru, C., Breunig, H. J. & Lork, E. (2003). Dalton Trans. pp. 4367–4374. Web of Science CSD CrossRef Google Scholar
Opris, L. M., Silvestru, A., Silvestru, C., Breunig, H. J. & Lork, E. (2004). Dalton Trans. pp. 3575–3585. Web of Science CSD CrossRef Google Scholar
Sharma, P., Castillo, D., Rosas, N., Cabrera, A., Gomez, E., Toscano, A., Lara, F., Hernández, S. & Espinosa, G. (2004). J. Organomet. Chem. 689, 2593–2600. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tokunaga, T., Seki, H., Yasuike, S., Ikoma, M., Kurita, J. & Yamaguchi, K. (2000a). Tetrahedron, 56, 8833–8839. Web of Science CSD CrossRef CAS Google Scholar
Tokunaga, T., Seki, H., Yasuike, S., Ikoma, M., Kurita, J. & Yamaguchi, K. (2000b). Tetrahedron Lett. 41, 1031–1034. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar