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

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.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in main residue
• R factor = 0.045
• wR factor = 0.112
• Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     3.441
            Value of mu given      =     3.301
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.63
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..          9
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          2
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.56 eA-3
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ          ?
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.25 Ratio
PLAT051_ALERT_1_C Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .       4.24 Perc.
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12    ..  CL1     ..       2.91 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14    ..  CL1     ..       2.86 Ang.

Alert level G
PLAT301_ALERT_3_G Note: Main Residue  Disorder ...................       4.00 Perc.
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2
PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ...................      50.00 Perc.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  15 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

All hydrogen atoms, except H1 attached to N1, were placed in calculated positions using a riding model, with C—H = 0.93–0.97 Å and with Uiso=1.5Ueq (C) for methyl H and Uiso= 1.2Ueq (C) for aryl H. The methyl groups were allowed to rotate while retaining tetrahedral geometry. The H1 hydrogen atom attached to N1 nitrogen atom was located from the difference map and the N1—H1 distance was restrained to 0.86 Å. The two halide atoms were refined as substitutional disorder between chlorine and bromine, with 0.67 occupancy for Cl and 0.33 for Br for Cl1/Br1 and 0.75 occupancy for Br and 0.25 for Cl for Cl2/Br2.

Computing details

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

	Fig. 1. A view of the asymmetric unit showing the atom-numbering scheme at 30% probability thermal ellipsoids for the (RN2,CSb1) isomer.
	Fig. 2. Molecular structure at 30% probability ellipsoids of (RN2,CSb1) (a) and (SN2,ASb1) (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-(RN2,CSb1) (thick lines) and all-(SN2,ASb1) (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-(RN2,CSb1) and all-(SN2,ASb1) 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

Crystal data

[SbBr0.33Cl0.67(C9H13N)(C9H12N)]Br0.75Cl0.25	F(000) = 1000
Mr = 510.07	Dx = 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) Å^3	0.28 × 0.22 × 0.18 mm
Z = 4

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0441P)^2 + 3.758P] where P = (Fo^2 + 2Fc^2)/3
3745 reflections	(Δ/σ)max < 0.001
216 parameters	Δρmax = 1.47 e Å^−3
2 restraints	Δρmin = −0.56 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2^i	0.86 (6)	2.39	3.220 (7)	164
C12—H12···Cl1^ii	0.93	2.91	3.827 (6)	167
C14—H14···Cl1^iii	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.