Substitutional disorder in the ionic diorganoanti­mony halide adduct [bromido/chlorido(0.33/0.67)][2-(di­methyl­amino­meth­yl)phen­yl][2-(di­methyl­ammonio­meth­yl)phen­yl]anti­mony(III) 0.75-bromide 0.25-chloride

Soran, A.P.; Bojan, V.R.

doi:10.1107/S1600536810009797

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages m423-m424

doi:10.1107/S1600536810009797

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Substitutional disorder in the ionic diorganoantimony halide adduct [bromido/chlorido(0.33/0.67)][2-(dimethylaminomethyl)phenyl][2-(dimethylammoniomethyl)phenyl]antimony(III) 0.75-bromide 0.25-chloride

Albert P. Soran ^a ^* and Vilma R. Bojan ^a

^aFaculty of Chemistry and Chemical Engineering, Babes-Bolyai University, Arany Janos Street, No. 11, RO-400028, Cluj Napoca, Romania
^*Correspondence e-mail: asoran@chem.ubbcluj.ro

(Received 20 January 2010; accepted 16 March 2010; online 20 March 2010)

The title complex, [SbBr_0.33Cl_0.67(C₉H₁₃N)(C₉H₁₂N)]Br_0.75Cl_0.25, exhibits substitutional disorder of both halogen atoms in the asymmetric unit, however, with different occupancies. Thus, the halogen atom bonded to Sb has 0.67 (4) occupancy for Cl and 0.33 (4) for Br, while the anionic halogen atom shows 0.75 (4) occupancy for Br and 0.25 (4) for Cl. An N—H⋯Cl/Br hydrogen bond is established between the cation and the halide anion. The coordination geometry of the Sb center in the cation is distorted pseudo-trigonal-bipyramidal as a result of the strong intramolecular N→Sb coordination trans to the Sb—Cl/Br bond. The pendant arm on the second ligand is twisted away from the metal center. The compound crystallizes as a racemate, i.e. a mixture of (R_N2,C_Sb1) and (S_N2,A_Sb1) isomers with respect to planar chirality induced by the coordinating N atom and chelate-induced Sb chirality. These isomers are associated through C_phenyl—H⋯Cl/Br hydrogen bonds, forming a three-dimensional architecture.

Related literature

For an isostructural compound, see: Opris et al. (2003 ). For related ionic organoantimony adducts, see: Sharma et al. (2004 ). For the chirality induced by the coordination of the N atom, see: IUPAC (1979 , 2005 ). For Sb—N distances, see: Emsley (1994 ).

Experimental

Crystal data

[SbBr_0.33Cl_0.67(C₉H₁₃N)(C₉H₁₂N)]Br_0.75Cl_0.25
M_r = 510.07
Monoclinic, P 2₁ /c
a = 13.8159 (19) Å
b = 12.6775 (18) Å
c = 12.5984 (17) Å
β = 105.342 (3)°
V = 2128.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 3.30 mm⁻¹
T = 297 K
0.28 × 0.22 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.458, T_max = 0.588
15150 measured reflections
3745 independent reflections
3298 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.112
S = 1.15
3745 reflections
216 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.47 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

X = Cl/Br.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯X2ⁱ	0.86 (6)	2.39	3.220 (7)	164
C12—H12⋯X1ⁱⁱ	0.93	2.91	3.827 (6)	167
C14—H14⋯X1ⁱⁱⁱ	0.93	2.86	3.766 (8)	164
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z.

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); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: enCIFer (Allen et al., 2004 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009797/zb2001sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810009797/zb2001Isup2.hkl

checkCIF report

Comment top

The chlorido/bromido[2-(dimethylaminomethyl)phenyl][2-(dimethylammoniomethyl)-phenyl]antimony chloride/bromide, [C₇₂H₁₀₀Br_4.32Cl_3.68N₈Sb₄], exhibits substitutional disorder of both halogen atoms of the asymmetric unit, however with different occupancies. Thus, the halogen bonded to Sb has 0.67 (4) occupancy for Cl and 0.33 (4) for Br while the anionic halogen shows 0.75 (4) occupancy for Br and 0.25 (4) for Cl.

A hydrogen bond is established between the cation and the halide anion [Cl2/Br2···H1 = 2.39 Å; N1—H1···Cl2/Br2 = 163.6°].

The title compound is isostructural with [{2-(Me₂NCH₂)C₆H₄}Sb{C₆H₄(CH₂NHMe₂)-2}]⁺[I]^- (Opris et al., 2003), having only a slightly smaller cell volume.

The coordination geometry of the Sb center in the cationic fragment is distorted, peudo-trigonal bipyramidal as a result of the strong intramolecular N→Sb coordination [Sb1—N2 = 2.414 (5) Å] trans to the Sb1—Cl1/Br1 bond [(N2—Sb1—Cl1/Br1 = 166.8 (1)°]. The pendant arm on the second ligand is twisted away from the metal center [non-bonding Sb1–N1 = 4.312 (6) Å] (Emsley, 1994), its N1 atom being protonated (Fig. 1.)

Coordination of N atom induces planar chirality, with the phenyl ring as chiral plane and the nitrogen as pilot atom (IUPAC, 1979). This intramolecular coordination of the nitrogen atom to antimony induces chirality at the Sb centre (IUPAC, 2005). Thus the compound crystallizes as a racemate, i.e. a mixture of (R_N2,C_Sb1) and (S_N2,A_Sb1) isomers (Fig. 2.), with two of each isomers in the unit cell.

Same kind of isomers form ribbon-like all-(R_N2,C_Sb1) and all-(S_N2,A_Sb1) polymers through [H12···.Cl1/Br1 = 2.91 Å] hydrogen bonds (Fig. 3.). These ribbon-like polymers are further associated through hydrogen bonds [H14···.Cl1/Br1 = 2.86 Å] to form a three-dimensional architecture (Fig. 4.)

Related literature top

For the isostructural compound [{2-(Me₂NCH₂)C₆H₄}Sb{C₆H₄(CH₂NHMe₂)-2}]⁺[I]^-, see: Opris et al. (2003). For related iterature [on what subject?], see: Sharma et al. (2004). For the chirality induced by the coordination of the N atom, see: IUPAC (1979, 2005). For Sb—N distances, see: Emsley (1994).

Experimental top

In the attempted synthesis of R₂SbMes from mesitylmagnesium bromide and R₂SbCl.(R = 2-Me₂NCH₂C₆H₄), crystals of the title compound were isolated from a chloroform-hexane mixture, due to partial hydrolysis followed by the protonation of one of the organic ligands.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: enCIFer (Allen et al., 2004) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. A view of the asymmetric unit showing the atom-numbering scheme at 30% probability thermal ellipsoids for the (R_N2,C_Sb1) isomer.
	Fig. 2. Molecular structure at 30% probability ellipsoids of (R_N2,C_Sb1) (a) and (S_N2,A_Sb1) (b) isomers present in crystals of the title compound. Only the cationic fragment is shown. All hydrogen atoms except H1 atoms have been omitted. Symmetry code: (i) 1-x, 1-y, -z.
	Fig. 3. Unit cell showing polymeric all-(R_N2,C_Sb1) (thick lines) and all-(S_N2,A_Sb1) (thin lines) strands formed as a result of H12···.Cl1/Br1 hydrogen bonding. All hydrogen atoms except H12 and H1 atoms have been omitted.
	Fig. 4. Three-dimensional network formed by polymeric all-(R_N2,C_Sb1) and all-(S_N2,A_Sb1) strands bridged by H14···Cl1/Br1 hydrogen bonds (thick green lines). All hydrogen atoms except H12, H14 and H1 atoms have been omitted.

[bromido/chlorido(0.33/0.67)][2-(dimethylaminomethyl)phenyl][2- (dimethylammoniomethyl)phenyl]antimony(III) 0.75-bromide 0.25-chloride top

Crystal data top

[SbBr_0.33Cl_0.67(C₉H₁₃N)(C₉H₁₂N)]Br_0.75Cl_0.25	F(000) = 1000
M_r = 510.07	D_x = 1.581 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3355 reflections
a = 13.8159 (19) Å	θ = 2.3–22.7°
b = 12.6775 (18) Å	µ = 3.30 mm⁻¹
c = 12.5984 (17) Å	T = 297 K
β = 105.342 (3)°	Block, colourless
V = 2128.0 (5) Å³	0.28 × 0.22 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3745 independent reflections
Radiation source: fine-focus sealed tube	3298 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
phi and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→16
T_min = 0.458, T_max = 0.588	k = −15→15
15150 measured reflections	l = −14→14

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) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ²(F_o²) + (0.0441P)² + 3.758P] where P = (F_o² + 2F_c²)/3
3745 reflections	(Δ/σ)_max < 0.001
216 parameters	Δρ_max = 1.47 e Å⁻³
2 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

[SbBr_0.33Cl_0.67(C₉H₁₃N)(C₉H₁₂N)]Br_0.75Cl_0.25	V = 2128.0 (5) Å³
M_r = 510.07	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.8159 (19) Å	µ = 3.30 mm⁻¹
b = 12.6775 (18) Å	T = 297 K
c = 12.5984 (17) Å	0.28 × 0.22 × 0.18 mm
β = 105.342 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3745 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3298 reflections with I > 2σ(I)
T_min = 0.458, T_max = 0.588	R_int = 0.044
15150 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	2 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	Δρ_max = 1.47 e Å⁻³
3745 reflections	Δρ_min = −0.56 e Å⁻³
216 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 > 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	Occ. (<1)
Br2	0.96752 (7)	0.33618 (8)	0.40075 (9)	0.0779 (3)	0.75
Br1	0.25490 (8)	0.45952 (8)	0.05792 (9)	0.0561 (3)	0.33
C1	0.2796 (4)	0.5553 (4)	0.3124 (4)	0.0415 (13)
C2	0.1990 (5)	0.5470 (5)	0.3592 (5)	0.0474 (14)
C3	0.2080 (5)	0.4808 (5)	0.4502 (5)	0.0593 (17)
H3	0.1550	0.4756	0.4825	0.071*
C4	0.2929 (6)	0.4238 (6)	0.4923 (5)	0.069 (2)
H4	0.2968	0.3790	0.5517	0.082*
C5	0.3730 (5)	0.4323 (5)	0.4473 (5)	0.0623 (18)
H5	0.4315	0.3943	0.4770	0.075*
C6	0.3662 (5)	0.4972 (5)	0.3581 (5)	0.0503 (15)
H6	0.4204	0.5024	0.3277	0.060*
C7	0.1020 (5)	0.6079 (5)	0.3195 (5)	0.0540 (16)
H7A	0.0884	0.6451	0.3813	0.065*
H7B	0.1100	0.6601	0.2662	0.065*
C8	0.0235 (6)	0.4925 (8)	0.1645 (6)	0.094 (3)
H8A	−0.0344	0.4499	0.1326	0.141*
H8B	0.0827	0.4494	0.1790	0.141*
H8C	0.0285	0.5478	0.1142	0.141*
C9	−0.0813 (6)	0.6012 (8)	0.2520 (9)	0.100 (3)
H9A	−0.0800	0.6602	0.2046	0.150*
H9B	−0.0867	0.6264	0.3221	0.150*
H9C	−0.1379	0.5572	0.2195	0.150*
C10	0.4296 (4)	0.6542 (4)	0.1811 (5)	0.0414 (13)
C11	0.4834 (4)	0.7263 (4)	0.2586 (5)	0.0435 (13)
C12	0.5832 (5)	0.7454 (5)	0.2665 (6)	0.0598 (17)
H12	0.6190	0.7925	0.3190	0.072*
C13	0.6304 (5)	0.6950 (5)	0.1970 (6)	0.0594 (17)
H13	0.6975	0.7094	0.2022	0.071*
C14	0.5804 (5)	0.6252 (5)	0.1218 (6)	0.0564 (16)
H14	0.6131	0.5908	0.0759	0.068*
C15	0.4796 (4)	0.6046 (5)	0.1128 (5)	0.0481 (14)
H15	0.4451	0.5569	0.0602	0.058*
C16	0.4306 (5)	0.7800 (5)	0.3341 (5)	0.0559 (16)
H16A	0.4337	0.7359	0.3979	0.067*
H16B	0.4634	0.8465	0.3595	0.067*
C17	0.3179 (6)	0.8851 (5)	0.1948 (6)	0.0618 (18)
H17A	0.3399	0.9496	0.2336	0.093*
H17B	0.2495	0.8926	0.1521	0.093*
H17C	0.3596	0.8696	0.1468	0.093*
C18	0.2643 (6)	0.8243 (6)	0.3521 (6)	0.0659 (19)
H18A	0.2700	0.7678	0.4042	0.099*
H18B	0.1952	0.8329	0.3122	0.099*
H18C	0.2885	0.8884	0.3905	0.099*
Cl1	0.25490 (8)	0.45952 (8)	0.05792 (9)	0.0561 (3)	0.67
Cl2	0.96752 (7)	0.33618 (8)	0.40075 (9)	0.0779 (3)	0.25
H1	0.008 (6)	0.492 (5)	0.315 (5)	0.08 (3)*
N1	0.0135 (4)	0.5386 (5)	0.2675 (5)	0.0636 (15)
N2	0.3249 (4)	0.7990 (4)	0.2740 (4)	0.0486 (12)
Sb1	0.27062 (3)	0.64376 (3)	0.16318 (3)	0.03907 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br2	0.0744 (6)	0.0738 (6)	0.0876 (7)	−0.0200 (5)	0.0252 (5)	−0.0053 (5)
Br1	0.0655 (7)	0.0544 (6)	0.0513 (6)	0.0023 (5)	0.0203 (5)	−0.0077 (5)
C1	0.053 (3)	0.041 (3)	0.030 (3)	0.002 (3)	0.010 (2)	0.000 (2)
C2	0.052 (4)	0.049 (3)	0.039 (3)	−0.006 (3)	0.009 (3)	−0.002 (3)
C3	0.064 (4)	0.073 (5)	0.043 (3)	−0.011 (4)	0.017 (3)	0.009 (3)
C4	0.085 (5)	0.071 (5)	0.042 (4)	−0.007 (4)	0.004 (4)	0.015 (3)
C5	0.069 (5)	0.053 (4)	0.054 (4)	0.007 (3)	−0.004 (3)	0.011 (3)
C6	0.050 (4)	0.054 (4)	0.046 (3)	0.004 (3)	0.012 (3)	0.001 (3)
C7	0.056 (4)	0.057 (4)	0.056 (4)	0.000 (3)	0.026 (3)	0.003 (3)
C8	0.077 (6)	0.135 (8)	0.064 (5)	−0.026 (5)	0.010 (4)	−0.011 (5)
C9	0.044 (4)	0.111 (7)	0.145 (9)	0.006 (4)	0.023 (5)	0.025 (6)
C10	0.042 (3)	0.044 (3)	0.040 (3)	0.002 (2)	0.013 (2)	0.004 (2)
C11	0.050 (3)	0.039 (3)	0.039 (3)	0.004 (3)	0.006 (3)	0.003 (2)
C12	0.054 (4)	0.052 (4)	0.063 (4)	−0.010 (3)	−0.002 (3)	0.005 (3)
C13	0.048 (4)	0.056 (4)	0.075 (5)	−0.001 (3)	0.018 (3)	0.013 (3)
C14	0.052 (4)	0.061 (4)	0.062 (4)	0.008 (3)	0.024 (3)	0.005 (3)
C15	0.050 (4)	0.052 (3)	0.041 (3)	0.000 (3)	0.012 (3)	−0.001 (3)
C16	0.062 (4)	0.052 (4)	0.049 (4)	0.000 (3)	0.007 (3)	−0.013 (3)
C17	0.076 (5)	0.040 (3)	0.067 (4)	0.003 (3)	0.015 (4)	0.003 (3)
C18	0.082 (5)	0.061 (4)	0.059 (4)	0.008 (4)	0.026 (4)	−0.018 (3)
Cl1	0.0655 (7)	0.0544 (6)	0.0513 (6)	0.0023 (5)	0.0203 (5)	−0.0077 (5)
Cl2	0.0744 (6)	0.0738 (6)	0.0876 (7)	−0.0200 (5)	0.0252 (5)	−0.0053 (5)
N1	0.050 (3)	0.076 (4)	0.067 (4)	−0.001 (3)	0.018 (3)	0.013 (3)
N2	0.062 (3)	0.041 (3)	0.044 (3)	0.004 (2)	0.016 (2)	−0.006 (2)
Sb1	0.0428 (2)	0.0423 (2)	0.0326 (2)	0.00455 (16)	0.01080 (16)	0.00087 (16)

Geometric parameters (Å, º) top

Br1—Sb1	2.6662 (11)	C10—C11	1.398 (8)
C1—C6	1.393 (8)	C10—Sb1	2.152 (6)
C1—C2	1.396 (8)	C11—C12	1.378 (9)
C1—Sb1	2.164 (5)	C11—C16	1.507 (8)
C2—C3	1.400 (8)	C12—C13	1.379 (9)
C2—C7	1.512 (9)	C12—H12	0.9300
C3—C4	1.359 (10)	C13—C14	1.347 (9)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.375 (10)	C14—C15	1.392 (9)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.376 (8)	C15—H15	0.9300
C5—H5	0.9300	C16—N2	1.476 (8)
C6—H6	0.9300	C16—H16A	0.9700
C7—N1	1.507 (8)	C16—H16B	0.9700
C7—H7A	0.9700	C17—N2	1.465 (8)
C7—H7B	0.9700	C17—H17A	0.9600
C8—N1	1.463 (10)	C17—H17B	0.9600
C8—H8A	0.9600	C17—H17C	0.9600
C8—H8B	0.9600	C18—N2	1.486 (8)
C8—H8C	0.9600	C18—H18A	0.9600
C9—N1	1.500 (9)	C18—H18B	0.9600
C9—H9A	0.9600	C18—H18C	0.9600
C9—H9B	0.9600	N1—H1	0.86 (6)
C9—H9C	0.9600	N2—Sb1	2.414 (5)
C10—C15	1.388 (8)

C6—C1—C2	118.6 (5)	C14—C13—C12	120.7 (6)
C6—C1—Sb1	118.6 (4)	C14—C13—H13	119.6
C2—C1—Sb1	122.5 (4)	C12—C13—H13	119.6
C1—C2—C3	118.9 (6)	C13—C14—C15	119.7 (6)
C1—C2—C7	123.9 (5)	C13—C14—H14	120.1
C3—C2—C7	117.2 (6)	C15—C14—H14	120.1
C4—C3—C2	121.3 (6)	C10—C15—C14	121.1 (6)
C4—C3—H3	119.4	C10—C15—H15	119.5
C2—C3—H3	119.4	C14—C15—H15	119.5
C3—C4—C5	120.2 (6)	N2—C16—C11	109.2 (5)
C3—C4—H4	119.9	N2—C16—H16A	109.8
C5—C4—H4	119.9	C11—C16—H16A	109.8
C4—C5—C6	119.6 (6)	N2—C16—H16B	109.8
C4—C5—H5	120.2	C11—C16—H16B	109.8
C6—C5—H5	120.2	H16A—C16—H16B	108.3
C5—C6—C1	121.4 (6)	N2—C17—H17A	109.5
C5—C6—H6	119.3	N2—C17—H17B	109.5
C1—C6—H6	119.3	H17A—C17—H17B	109.5
N1—C7—C2	113.1 (5)	N2—C17—H17C	109.5
N1—C7—H7A	109.0	H17A—C17—H17C	109.5
C2—C7—H7A	109.0	H17B—C17—H17C	109.5
N1—C7—H7B	109.0	N2—C18—H18A	109.5
C2—C7—H7B	109.0	N2—C18—H18B	109.5
H7A—C7—H7B	107.8	H18A—C18—H18B	109.5
N1—C8—H8A	109.5	N2—C18—H18C	109.5
N1—C8—H8B	109.5	H18A—C18—H18C	109.5
H8A—C8—H8B	109.5	H18B—C18—H18C	109.5
N1—C8—H8C	109.5	C8—N1—C9	112.3 (7)
H8A—C8—H8C	109.5	C8—N1—C7	111.3 (5)
H8B—C8—H8C	109.5	C9—N1—C7	109.2 (6)
N1—C9—H9A	109.5	C8—N1—H1	113 (5)
N1—C9—H9B	109.5	C9—N1—H1	103 (5)
H9A—C9—H9B	109.5	C7—N1—H1	108 (5)
N1—C9—H9C	109.5	C17—N2—C16	110.4 (5)
H9A—C9—H9C	109.5	C17—N2—C18	110.0 (5)
H9B—C9—H9C	109.5	C16—N2—C18	110.5 (5)
C15—C10—C11	118.0 (5)	C17—N2—Sb1	105.0 (4)
C15—C10—Sb1	124.6 (4)	C16—N2—Sb1	106.1 (3)
C11—C10—Sb1	116.9 (4)	C18—N2—Sb1	114.6 (4)
C12—C11—C10	120.2 (6)	C10—Sb1—C1	96.8 (2)
C12—C11—C16	121.2 (6)	C10—Sb1—N2	74.76 (19)
C10—C11—C16	118.6 (5)	C1—Sb1—N2	88.97 (18)
C11—C12—C13	120.3 (6)	C10—Sb1—Br1	93.01 (15)
C11—C12—H12	119.8	C1—Sb1—Br1	87.51 (14)
C13—C12—H12	119.8	N2—Sb1—Br1	166.78 (12)

C6—C1—C2—C3	0.0 (8)	C2—C7—N1—C8	−66.9 (7)
Sb1—C1—C2—C3	174.4 (4)	C2—C7—N1—C9	168.5 (6)
C6—C1—C2—C7	178.3 (6)	C11—C16—N2—C17	−73.5 (6)
Sb1—C1—C2—C7	−7.3 (8)	C11—C16—N2—C18	164.6 (5)
C1—C2—C3—C4	−0.9 (10)	C11—C16—N2—Sb1	39.8 (5)
C7—C2—C3—C4	−179.3 (6)	C15—C10—Sb1—C1	112.6 (5)
C2—C3—C4—C5	1.5 (11)	C11—C10—Sb1—C1	−75.7 (4)
C3—C4—C5—C6	−1.2 (11)	C15—C10—Sb1—N2	−160.4 (5)
C4—C5—C6—C1	0.3 (10)	C11—C10—Sb1—N2	11.3 (4)
C2—C1—C6—C5	0.3 (9)	C15—C10—Sb1—Br1	24.7 (5)
Sb1—C1—C6—C5	−174.3 (5)	C11—C10—Sb1—Br1	−163.6 (4)
C1—C2—C7—N1	112.2 (6)	C6—C1—Sb1—C10	−22.0 (5)
C3—C2—C7—N1	−69.5 (7)	C2—C1—Sb1—C10	163.7 (5)
C15—C10—C11—C12	−0.9 (8)	C6—C1—Sb1—N2	−96.5 (5)
Sb1—C10—C11—C12	−173.1 (4)	C2—C1—Sb1—N2	89.1 (5)
C15—C10—C11—C16	−179.4 (5)	C6—C1—Sb1—Br1	70.8 (4)
Sb1—C10—C11—C16	8.3 (7)	C2—C1—Sb1—Br1	−103.6 (4)
C10—C11—C12—C13	1.1 (9)	C17—N2—Sb1—C10	88.5 (4)
C16—C11—C12—C13	179.6 (6)	C16—N2—Sb1—C10	−28.5 (4)
C11—C12—C13—C14	−1.1 (10)	C18—N2—Sb1—C10	−150.6 (5)
C12—C13—C14—C15	0.9 (10)	C17—N2—Sb1—C1	−174.2 (4)
C11—C10—C15—C14	0.6 (9)	C16—N2—Sb1—C1	68.8 (4)
Sb1—C10—C15—C14	172.3 (5)	C18—N2—Sb1—C1	−53.3 (4)
C13—C14—C15—C10	−0.7 (9)	C17—N2—Sb1—Br1	111.3 (6)
C12—C11—C16—N2	146.5 (6)	C16—N2—Sb1—Br1	−5.7 (8)
C10—C11—C16—N2	−34.9 (7)	C18—N2—Sb1—Br1	−127.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2ⁱ	0.86 (6)	2.39	3.220 (7)	164
C12—H12···Cl1ⁱⁱ	0.93	2.91	3.827 (6)	167
C14—H14···Cl1ⁱⁱⁱ	0.93	2.86	3.766 (8)	164

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

Experimental details

Crystal data
Chemical formula	[SbBr_0.33Cl_0.67(C₉H₁₃N)(C₉H₁₂N)]Br_0.75Cl_0.25
M_r	510.07
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	297
a, b, c (Å)	13.8159 (19), 12.6775 (18), 12.5984 (17)
β (°)	105.342 (3)
V (Å³)	2128.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.30
Crystal size (mm)	0.28 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.458, 0.588
No. of measured, independent and observed [I > 2σ(I)] reflections	15150, 3745, 3298
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.112, 1.15
No. of reflections	3745
No. of parameters	216
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.47, −0.56

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), enCIFer (Allen et al., 2004) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2ⁱ	0.86 (6)	2.39	3.220 (7)	164
C12—H12···Cl1ⁱⁱ	0.93	2.91	3.827 (6)	167
C14—H14···Cl1ⁱⁱⁱ	0.93	2.86	3.766 (8)	164

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

Acknowledgements

Financial support from the National University Research Council (Research Project PNII-ID 2052/2009) is greatly appreciated. We also thank the National Center for X-ray Diffraction (Babes-Bolyai University, Cluj-Napoca, Romania) for support of the solid-state structure determinations.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338. Web of Science CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. 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
Emsley, J. (1994). Die Elemente. Berlin: Walter de Gruyter. Google Scholar
IUPAC (1979). Nomenclature of Organic Chemistry. Oxford: Pergamon Press. Google Scholar
IUPAC (2005). Nomenclature of Inorganic Chemistry, IUPAC Recommendations 2005. Cambridge, England: RSC Publishing. 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
Sharma, P., Castillo, D., Rosas, N., Cabrera, A., Gomez, E., Toscano, A., Lara, F., Hernandez, 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
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar

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Volume 66| Part 4| April 2010| Pages m423-m424

doi:10.1107/S1600536810009797

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Substitutional disorder in the ionic diorgano­anti­mony halide adduct [bromido/chlorido(0.33/0.67)][2-(di­methyl­amino­meth­yl)phen­yl][2-(di­methyl­ammonio­meth­yl)phen­yl]anti­mony(III) 0.75-bromide 0.25-chloride

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Substitutional disorder in the ionic diorganoantimony halide adduct [bromido/chlorido(0.33/0.67)][2-(dimethylaminomethyl)phenyl][2-(dimethylammoniomethyl)phenyl]antimony(III) 0.75-bromide 0.25-chloride