7α,15α-Dibromo-8,16-diphenyl-6,7,14,15-tetra­hydro-6α,14α-epithio­cyclo­octa­[1,2-b:5,6-b′]diquinoline deuterochloro­form solvate

Chan, I.Y.H.; Bishop, R.; Craig, D.C.; Bhadbhade, M.M.; Scudder, M.L.

doi:10.1107/S1600536809032978

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2253

doi:10.1107/S1600536809032978

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7α,15α-Dibromo-8,16-diphenyl-6,7,14,15-tetrahydro-6α,14α-epithiocycloocta[1,2-b:5,6-b′]diquinoline deuterochloroform solvate

Isa Y. H. Chan,^a Roger Bishop,^a Donald C. Craig,^a Mohan M. Bhadbhade ^b and Marcia L. Scudder ^a ^*

^aSchool of Chemistry, University of New South Wales, Sydney 2052, Australia, and ^bThe Analytical Centre, University of New South Wales, Sydney 2052, Australia
^*Correspondence e-mail: m.scudder@unsw.edu.au

(Received 7 August 2009; accepted 19 August 2009; online 26 August 2009)

In the racemic title compound, C₃₄H₂₂Br₂N₂S·CDCl₃, pairs of diquinoline host molecules form centrosymmetric brick-like dimers utilizing three different aryl edge-to-face interactions (EF_1–3). The dimeric (EF)₆ (i.e. 2 × EF_1–3) building blocks pack with the deuterochloroform guest molecules positioned near each of their corners. The Cl atoms of the latter are disordered over two sets of sites in a 0.53 (2):0.47 (2) ratio.

Related literature

The solvent-free C₃₄H₂₂Br₂N₂S molecule crystallizes in space group C2/c exhibiting a layer structure that does not contain (EF)₆ bricks (Alshahateet et al., 2008 ). These bricks are, however, present in five alternative inclusion crystal structures formed by the same host (Alshahateet et al., 2008). Similar dimeric (EF)₆ building blocks have also been found in crystal structures of other structurally related racemic diquinoline molecules (Ashmore et al., 2004 , 2009 ).

Experimental

Crystal data

C₃₄H₂₂Br₂N₂S·CDCl₃
M_r = 770.81
Triclinic, $[P \overline 1]$
a = 10.161 (4) Å
b = 10.246 (5) Å
c = 15.868 (6) Å
α = 93.88 (3)°
β = 99.43 (3)°
γ = 92.50 (3)°
V = 1623.4 (12) Å³
Z = 2
Mo Kα radiation
μ = 2.84 mm⁻¹
T = 294 K
0.26 × 0.24 × 0.12 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: analytical (de Meulenaer & Tompa, 1965 ) T_min = 0.489, T_max = 0.712
5894 measured reflections
5692 independent reflections
4210 reflections with I > 2σ(I)
R_int = 0.032
1 standard reflections frequency: 30 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.130
S = 0.84
5692 reflections
432 parameters
436 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Data collection: CAD-4 Manual (Schagen et al., 1989 ); cell refinement: CAD-4 Manual; data reduction: CAD-4 Manual; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and CrystalMaker (CrystalMaker, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032978/hb5037sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032978/hb5037Isup2.hkl

checkCIF report

Comment top

The structure of (I).CDCl₃ is shown in Fig. 1. (I) is chiral, but in the racemic crystal, two molecules related by a centre of inversion form dimeric brick units, associating by means of pairs of three different edge-face interactions (EF_1–3, Fig. 2). These (EF)₆ brick units have previously been found to be present in five other crystal structures formed by the same diquinoline host (I) with other solvent inclusion (Alshahateet et al., 2008). In addition, similar dimeric (EF)₆ building blocks have been found in crystal structures of other inclusion compounds of structurally related racemic diquinoline molecules (Ashmore et al., 2004 and 2009). However, when (I) was previously obtained from CHCl₃ as solvent-free crystals in space group C2/c a layer structure resulted that did not contain (EF)₆ bricks (Alshahateet et al., 2008). Formation of the solvent-free or lattice inclusion crystal forms is probably influenced by the crystallization temperature rather than by the isotopic substitution of the chloroform solvent.

The CDCl₃ guest is disordered over two sites [occupancies 0.53 (2) and 0.47 (2)] and is located at the corners of the dimeric bricks. Additional lattice stabilization results from host-host and host–guest halogen···halogen and C—H(or D)···halogen interactions.

Related literature top

The solvent-free C₃₄H₂₂Br₂N₂S molecule crystallizes in space group C2/c exhibiting a layer structure that does not contain (EF)₆ bricks (Alshahateet et al., 2008). These bricks are, however, present in five alternative inclusion crystal structures formed by the same host (Alshahateet et al., 2008). Similar dimeric (EF)₆ building blocks have also been found in crystal structures of other structurally related racemic diquinoline molecules (Ashmore et al., 2004, 2009).

Experimental top

Racemic 7α,15α-dibromo-8,16-diphenyl-6,7,14,15-tetrahydro-6α,14α-thiacycloocta[1,2-b:5,6-b']diquinoline was prepared as previously described (Alshahateet et al., 2008) and colourless blocks of (I) were obtained by slow concentration of a deuterochloroform solution.

Computing details top

Data collection: CAD-4 Manual (Schagen et al., 1989); cell refinement: CAD-4 Manual (Schagen et al., 1989); data reduction: CAD-4 Manual (Schagen et al., 1989); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CrystalMaker (CrystalMaker, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with ellipsoids drawn at 30% probability level. The second disorder component of the solvent has been omitted for clarity.
	Fig. 2. Unit cell diagram of (I) indicating the three different edge-face interactions, EF_1–3.

7α,15α-Dibromo-8,16-diphenyl-6,7,14,15-tetrahydro-6α,14α- epithiocycloocta[1,2-b:5,6-b']diquinoline deuterochloroform solvate top

Crystal data top

C₃₄H₂₂Br₂N₂S·CDCl₃	Z = 2
M_r = 770.81	F(000) = 768
Triclinic, P1	D_x = 1.575 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.161 (4) Å	Cell parameters from 11 reflections
b = 10.246 (5) Å	θ = 10.0–11.0°
c = 15.868 (6) Å	µ = 2.84 mm⁻¹
α = 93.88 (3)°	T = 294 K
β = 99.43 (3)°	Blocks, colourless
γ = 92.50 (3)°	0.26 × 0.24 × 0.12 mm
V = 1623.4 (12) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	4210 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
ω–2θ scans	h = −12→11
Absorption correction: analytical (de Meulenaer & Tompa, 1965)	k = −12→12
T_min = 0.489, T_max = 0.712	l = 0→18
5894 measured reflections	1 standard reflections every 30 min
5692 independent reflections	intensity decay: none

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) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 0.84	w = 1/[σ²(F_o²) + (0.1P)² + P] where P = (F_o² + 2F_c²)/3
5692 reflections	(Δ/σ)_max < 0.001
432 parameters	Δρ_max = 0.50 e Å⁻³
436 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

C₃₄H₂₂Br₂N₂S·CDCl₃	γ = 92.50 (3)°
M_r = 770.81	V = 1623.4 (12) Å³
Triclinic, P1	Z = 2
a = 10.161 (4) Å	Mo Kα radiation
b = 10.246 (5) Å	µ = 2.84 mm⁻¹
c = 15.868 (6) Å	T = 294 K
α = 93.88 (3)°	0.26 × 0.24 × 0.12 mm
β = 99.43 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	4210 reflections with I > 2σ(I)
Absorption correction: analytical (de Meulenaer & Tompa, 1965)	R_int = 0.032
T_min = 0.489, T_max = 0.712	1 standard reflections every 30 min
5894 measured reflections	intensity decay: none
5692 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	436 restraints
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 0.84	Δρ_max = 0.50 e Å⁻³
5692 reflections	Δρ_min = −0.64 e Å⁻³
432 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. The orientational disorder of CDCl₃ (about the C1C'-H1C' bond) over two major sites (in 52:48 ratio) was modelled using PART instruction in SHELXL97. The molecular geometry of CDCl₃ was restrained to have values within the observed range; anisotropic thermal parameters of the disordered atoms were also restrained using the same program.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1C'	0.0673 (7)	0.8408 (6)	0.8664 (4)	0.114 (2)
D1C'	0.0960	0.7680	0.9030	0.137*
Cl1C	0.1613 (13)	0.9741 (11)	0.9107 (9)	0.197 (5)	0.53 (2)
Cl2C	0.0864 (11)	0.7870 (9)	0.7614 (4)	0.163 (4)	0.53 (2)
Cl3C	−0.1006 (7)	0.8557 (12)	0.8705 (10)	0.142 (3)	0.53 (2)
Cl1'	0.1385 (9)	0.9940 (6)	0.9039 (8)	0.141 (3)	0.47 (2)
Cl2'	0.0872 (12)	0.835 (2)	0.7613 (5)	0.208 (5)	0.47 (2)
Cl3'	−0.0929 (12)	0.8162 (17)	0.8811 (15)	0.198 (6)	0.47 (2)
Br1	0.12588 (5)	0.05682 (4)	0.58378 (3)	0.05792 (17)
Br2	0.22328 (4)	0.53263 (4)	0.90496 (3)	0.04953 (15)
N1	0.1465 (3)	0.5410 (3)	0.6081 (2)	0.0426 (8)
N2	0.4967 (3)	0.2104 (3)	0.7913 (2)	0.0383 (7)
S1	0.11551 (10)	0.26209 (10)	0.76288 (7)	0.0448 (3)
C1	0.1492 (4)	0.4236 (4)	0.7312 (2)	0.0390 (9)
C2	0.1736 (4)	0.4270 (4)	0.6392 (2)	0.0369 (8)
C3	0.2294 (4)	0.3238 (4)	0.5954 (2)	0.0368 (8)
C4	0.2600 (4)	0.1981 (4)	0.6354 (2)	0.0386 (8)
C5	0.2671 (4)	0.2031 (4)	0.7328 (3)	0.0391 (8)
C6	0.3919 (4)	0.2822 (4)	0.7772 (2)	0.0349 (8)
C7	0.3956 (4)	0.4196 (3)	0.7990 (2)	0.0329 (8)
C8	0.2695 (4)	0.4926 (4)	0.7892 (2)	0.0383 (9)
C9	0.1710 (4)	0.5593 (4)	0.5278 (3)	0.0430 (9)
C10	0.1405 (5)	0.6812 (4)	0.4937 (3)	0.0531 (11)
H10	0.1031	0.7466	0.5264	0.064*
C11	0.1644 (5)	0.7041 (5)	0.4151 (3)	0.0625 (12)
H11	0.1433	0.7858	0.3929	0.075*
C12	0.2197 (5)	0.6107 (5)	0.3651 (3)	0.0650 (13)
H12	0.2363	0.6294	0.3099	0.078*
C13	0.2499 (5)	0.4924 (5)	0.3959 (3)	0.0571 (11)
H13	0.2862	0.4286	0.3614	0.069*
C14	0.2278 (4)	0.4640 (4)	0.4783 (3)	0.0447 (9)
C15	0.2573 (4)	0.3430 (4)	0.5148 (3)	0.0421 (9)
C16	0.6163 (4)	0.2717 (4)	0.8271 (2)	0.0382 (8)
C17	0.7270 (4)	0.1935 (4)	0.8455 (3)	0.0471 (10)
H17	0.7161	0.1011	0.8340	0.056*
C18	0.8490 (4)	0.2505 (5)	0.8796 (3)	0.0555 (11)
H18	0.9224	0.1969	0.8931	0.067*
C19	0.8689 (4)	0.3867 (5)	0.8953 (3)	0.0579 (12)
H19	0.9556	0.4253	0.9170	0.070*
C20	0.7626 (4)	0.4635 (4)	0.8792 (3)	0.0492 (10)
H20	0.7764	0.5557	0.8905	0.059*
C21	0.6328 (4)	0.4095 (4)	0.8463 (2)	0.0382 (8)
C22	0.5179 (4)	0.4835 (4)	0.8319 (2)	0.0373 (8)
C23	0.3176 (5)	0.2394 (4)	0.4643 (3)	0.0479 (10)
C24	0.4528 (5)	0.2252 (5)	0.4776 (3)	0.0635 (13)
H24	0.5103	0.2831	0.5181	0.076*
C25	0.5059 (7)	0.1250 (7)	0.4310 (4)	0.0881 (19)
H25	0.5993	0.1139	0.4411	0.106*
C26	0.4250 (8)	0.0445 (6)	0.3721 (4)	0.0868 (18)
H26	0.4616	−0.0228	0.3405	0.104*
C27	0.2903 (8)	0.0594 (6)	0.3575 (4)	0.0859 (17)
H27	0.2339	0.0020	0.3159	0.103*
C28	0.2352 (6)	0.1577 (5)	0.4029 (3)	0.0686 (14)
H28	0.1417	0.1687	0.3919	0.082*
C29	0.5295 (4)	0.6274 (4)	0.8582 (3)	0.0404 (9)
C30	0.5095 (5)	0.7195 (4)	0.7992 (3)	0.0535 (11)
H30	0.4902	0.6929	0.7398	0.064*
C31	0.5173 (6)	0.8518 (5)	0.8265 (4)	0.0708 (14)
H31	0.5026	0.9153	0.7855	0.085*
C32	0.5463 (6)	0.8915 (5)	0.9125 (4)	0.0700 (14)
H32	0.5513	0.9821	0.9306	0.084*
C33	0.5677 (5)	0.8008 (5)	0.9714 (3)	0.0631 (13)
H33	0.5890	0.8278	1.0308	0.076*
C34	0.5582 (5)	0.6691 (4)	0.9444 (3)	0.0498 (10)
H34	0.5716	0.6060	0.9858	0.060*
H1	0.080 (4)	0.472 (4)	0.739 (2)	0.038 (11)*
H4	0.349 (4)	0.158 (4)	0.622 (2)	0.039 (10)*
H5	0.273 (4)	0.120 (4)	0.751 (3)	0.038 (10)*
H8	0.284 (4)	0.577 (4)	0.775 (2)	0.036 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1C'	0.137 (5)	0.087 (4)	0.128 (5)	0.040 (4)	0.037 (5)	0.015 (4)
Cl1C	0.137 (6)	0.205 (9)	0.220 (9)	−0.029 (6)	−0.043 (7)	0.019 (6)
Cl2C	0.225 (8)	0.167 (5)	0.118 (4)	0.147 (6)	0.045 (4)	0.039 (3)
Cl3C	0.106 (4)	0.095 (6)	0.236 (8)	0.010 (3)	0.065 (4)	0.009 (5)
Cl1'	0.118 (5)	0.063 (3)	0.256 (10)	0.012 (3)	0.068 (6)	0.006 (4)
Cl2'	0.159 (8)	0.369 (16)	0.091 (4)	0.013 (9)	−0.004 (4)	0.044 (6)
Cl3'	0.179 (8)	0.110 (9)	0.323 (14)	−0.048 (6)	0.106 (9)	0.018 (8)
Br1	0.0681 (3)	0.0409 (3)	0.0561 (3)	−0.0073 (2)	−0.0066 (2)	−0.0104 (2)
Br2	0.0486 (3)	0.0618 (3)	0.0377 (2)	0.0112 (2)	0.00862 (18)	−0.00863 (19)
N1	0.0443 (19)	0.0419 (19)	0.0382 (18)	0.0076 (15)	−0.0018 (15)	−0.0026 (14)
N2	0.0404 (17)	0.0361 (17)	0.0378 (17)	0.0034 (14)	0.0062 (14)	−0.0016 (14)
S1	0.0413 (6)	0.0459 (6)	0.0466 (6)	−0.0004 (4)	0.0075 (4)	0.0001 (5)
C1	0.039 (2)	0.041 (2)	0.036 (2)	0.0077 (17)	0.0047 (17)	−0.0043 (16)
C2	0.0314 (19)	0.039 (2)	0.038 (2)	0.0019 (15)	0.0013 (15)	−0.0015 (16)
C3	0.035 (2)	0.036 (2)	0.0352 (19)	−0.0008 (15)	−0.0010 (16)	−0.0053 (15)
C4	0.042 (2)	0.034 (2)	0.036 (2)	−0.0020 (16)	−0.0009 (16)	−0.0065 (16)
C5	0.040 (2)	0.032 (2)	0.044 (2)	0.0012 (16)	0.0022 (17)	0.0042 (17)
C6	0.039 (2)	0.037 (2)	0.0287 (18)	0.0028 (15)	0.0078 (15)	0.0004 (15)
C7	0.0392 (19)	0.0315 (18)	0.0279 (18)	0.0037 (15)	0.0062 (15)	−0.0027 (14)
C8	0.041 (2)	0.041 (2)	0.0328 (19)	0.0089 (17)	0.0073 (16)	−0.0042 (17)
C9	0.046 (2)	0.038 (2)	0.041 (2)	0.0068 (17)	−0.0061 (17)	−0.0001 (16)
C10	0.062 (3)	0.045 (2)	0.051 (3)	0.008 (2)	0.002 (2)	0.0029 (19)
C11	0.072 (3)	0.054 (3)	0.059 (3)	0.005 (2)	−0.003 (2)	0.016 (2)
C12	0.075 (3)	0.073 (3)	0.047 (3)	0.002 (3)	0.008 (2)	0.017 (2)
C13	0.067 (3)	0.060 (3)	0.046 (2)	0.012 (2)	0.013 (2)	0.006 (2)
C14	0.046 (2)	0.049 (2)	0.038 (2)	0.0064 (18)	0.0017 (18)	0.0002 (17)
C15	0.039 (2)	0.046 (2)	0.038 (2)	0.0046 (17)	0.0002 (17)	−0.0051 (16)
C16	0.040 (2)	0.042 (2)	0.033 (2)	0.0051 (16)	0.0083 (16)	0.0000 (16)
C17	0.046 (2)	0.049 (2)	0.048 (2)	0.0093 (18)	0.0102 (19)	−0.0002 (19)
C18	0.036 (2)	0.072 (3)	0.059 (3)	0.013 (2)	0.009 (2)	0.000 (2)
C19	0.035 (2)	0.075 (3)	0.062 (3)	0.001 (2)	0.010 (2)	−0.009 (2)
C20	0.042 (2)	0.052 (2)	0.053 (3)	−0.0040 (18)	0.0112 (19)	−0.007 (2)
C21	0.039 (2)	0.045 (2)	0.032 (2)	0.0013 (16)	0.0108 (16)	−0.0037 (16)
C22	0.045 (2)	0.039 (2)	0.0282 (18)	0.0000 (16)	0.0089 (16)	−0.0004 (15)
C23	0.061 (3)	0.044 (2)	0.040 (2)	0.0096 (19)	0.0114 (19)	−0.0020 (18)
C24	0.067 (3)	0.070 (3)	0.057 (3)	0.021 (2)	0.015 (2)	0.005 (2)
C25	0.096 (4)	0.112 (5)	0.066 (4)	0.060 (4)	0.027 (3)	0.008 (3)
C26	0.148 (5)	0.069 (4)	0.057 (3)	0.051 (4)	0.042 (4)	0.008 (3)
C27	0.137 (5)	0.063 (3)	0.058 (3)	0.009 (4)	0.025 (3)	−0.018 (3)
C28	0.086 (4)	0.068 (3)	0.048 (3)	0.009 (3)	0.008 (2)	−0.020 (2)
C29	0.038 (2)	0.038 (2)	0.045 (2)	0.0015 (16)	0.0084 (17)	−0.0039 (17)
C30	0.070 (3)	0.045 (2)	0.046 (2)	−0.004 (2)	0.015 (2)	0.0007 (19)
C31	0.099 (4)	0.043 (3)	0.077 (3)	0.004 (3)	0.029 (3)	0.016 (2)
C32	0.096 (4)	0.038 (3)	0.081 (3)	−0.004 (2)	0.036 (3)	−0.010 (2)
C33	0.078 (3)	0.051 (3)	0.057 (3)	−0.008 (2)	0.015 (3)	−0.018 (2)
C34	0.062 (3)	0.043 (2)	0.042 (2)	0.000 (2)	0.008 (2)	−0.0035 (18)

Geometric parameters (Å, º) top

C1C'—Cl1C	1.676 (8)	C13—H13	0.9500
C1C'—Cl2C	1.765 (8)	C14—C15	1.427 (6)
C1C'—Cl3C	1.730 (9)	C15—C23	1.500 (6)
C1C'—Cl1'	1.724 (9)	C16—C17	1.412 (6)
C1C'—Cl2'	1.711 (10)	C16—C21	1.421 (6)
C1C'—Cl3'	1.692 (12)	C17—C18	1.358 (6)
C1C'—D1C'	1.0000	C17—H17	0.9500
Br1—C4	1.981 (4)	C18—C19	1.400 (7)
Br2—C8	1.990 (4)	C18—H18	0.9500
N1—C2	1.322 (5)	C19—C20	1.363 (6)
N1—C9	1.361 (5)	C19—H19	0.9500
N2—C6	1.319 (5)	C20—C21	1.411 (6)
N2—C16	1.361 (5)	C20—H20	0.9500
S1—C1	1.796 (4)	C21—C22	1.415 (5)
S1—C5	1.802 (4)	C22—C29	1.499 (5)
C1—C8	1.519 (6)	C23—C24	1.370 (7)
C1—C2	1.523 (5)	C23—C28	1.382 (7)
C1—H1	0.89 (4)	C24—C25	1.402 (7)
C2—C3	1.416 (5)	C24—H24	0.9500
C3—C15	1.378 (6)	C25—C26	1.348 (9)
C3—C4	1.497 (5)	C25—H25	0.9500
C4—C5	1.532 (6)	C26—C27	1.367 (9)
C4—H4	1.06 (4)	C26—H26	0.9500
C5—C6	1.517 (5)	C27—C28	1.390 (7)
C5—H5	0.92 (4)	C27—H27	0.9500
C6—C7	1.425 (5)	C28—H28	0.9500
C7—C22	1.385 (5)	C29—C30	1.372 (6)
C7—C8	1.503 (5)	C29—C34	1.386 (6)
C8—H8	0.92 (4)	C30—C31	1.389 (6)
C9—C14	1.413 (6)	C30—H30	0.9500
C9—C10	1.422 (6)	C31—C32	1.377 (7)
C10—C11	1.343 (7)	C31—H31	0.9500
C10—H10	0.9500	C32—C33	1.362 (7)
C11—C12	1.396 (7)	C32—H32	0.9500
C11—H11	0.9500	C33—C34	1.382 (6)
C12—C13	1.365 (7)	C33—H33	0.9500
C12—H12	0.9500	C34—H34	0.9500
C13—C14	1.410 (6)

Cl1C—C1C'—Cl2C	116.3 (8)	C14—C13—H13	119.6
Cl1C—C1C'—Cl3C	112.5 (7)	C13—C14—C9	118.7 (4)
Cl3C—C1C'—Cl2C	109.4 (7)	C13—C14—C15	123.9 (4)
Cl2'—C1C'—Cl1'	101.7 (9)	C9—C14—C15	117.4 (4)
Cl3'—C1C'—Cl1'	114.3 (7)	C3—C15—C14	119.4 (4)
Cl3'—C1C'—Cl2'	114.2 (10)	C3—C15—C23	121.6 (4)
Cl1C—C1C'—D1C'	106.0	C14—C15—C23	119.0 (4)
Cl2C—C1C'—D1C'	106.0	N2—C16—C17	117.8 (4)
Cl3C—C1C'—D1C'	106.0	N2—C16—C21	122.5 (3)
Cl1'—C1C'—D1C'	115.4	C17—C16—C21	119.7 (4)
Cl2'—C1C'—D1C'	120.7	C18—C17—C16	119.9 (4)
Cl3'—C1C'—D1C'	91.2	C18—C17—H17	120.0
C2—N1—C9	117.7 (3)	C16—C17—H17	120.0
C6—N2—C16	118.1 (3)	C17—C18—C19	121.4 (4)
C1—S1—C5	92.66 (19)	C17—C18—H18	119.3
C8—C1—C2	107.7 (3)	C19—C18—H18	119.3
C8—C1—S1	111.4 (3)	C20—C19—C18	119.4 (4)
C2—C1—S1	114.3 (3)	C20—C19—H19	120.3
C8—C1—H1	105 (3)	C18—C19—H19	120.3
C2—C1—H1	109 (3)	C19—C20—C21	121.8 (4)
S1—C1—H1	109 (3)	C19—C20—H20	119.1
N1—C2—C3	124.4 (4)	C21—C20—H20	119.1
N1—C2—C1	111.9 (3)	C20—C21—C22	124.3 (4)
C3—C2—C1	123.5 (3)	C20—C21—C16	117.7 (4)
C15—C3—C2	118.1 (4)	C22—C21—C16	117.9 (3)
C15—C3—C4	120.6 (3)	C7—C22—C21	119.1 (3)
C2—C3—C4	121.4 (3)	C7—C22—C29	121.4 (3)
C3—C4—C5	115.5 (3)	C21—C22—C29	119.4 (3)
C3—C4—Br1	110.4 (3)	C24—C23—C28	119.7 (4)
C5—C4—Br1	107.7 (3)	C24—C23—C15	121.1 (4)
C3—C4—H4	114 (2)	C28—C23—C15	119.2 (4)
C5—C4—H4	107 (2)	C23—C24—C25	119.7 (5)
Br1—C4—H4	101 (2)	C23—C24—H24	120.1
C6—C5—C4	110.1 (3)	C25—C24—H24	120.1
C6—C5—S1	113.3 (3)	C26—C25—C24	120.3 (6)
C4—C5—S1	110.8 (3)	C26—C25—H25	119.8
C6—C5—H5	107 (2)	C24—C25—H25	119.8
C4—C5—H5	110 (2)	C25—C26—C27	120.2 (5)
S1—C5—H5	106 (2)	C25—C26—H26	119.9
N2—C6—C7	123.9 (3)	C27—C26—H26	119.9
N2—C6—C5	112.6 (3)	C26—C27—C28	120.6 (6)
C7—C6—C5	123.4 (3)	C26—C27—H27	119.7
C22—C7—C6	118.2 (3)	C28—C27—H27	119.7
C22—C7—C8	120.9 (3)	C23—C28—C27	119.3 (6)
C6—C7—C8	120.9 (3)	C23—C28—H28	120.3
C7—C8—C1	115.8 (3)	C27—C28—H28	120.3
C7—C8—Br2	108.5 (3)	C30—C29—C34	118.7 (4)
C1—C8—Br2	109.1 (3)	C30—C29—C22	121.9 (4)
C7—C8—H8	112 (2)	C34—C29—C22	119.4 (4)
C1—C8—H8	112 (2)	C29—C30—C31	120.0 (4)
Br2—C8—H8	99 (2)	C29—C30—H30	120.0
N1—C9—C14	123.0 (4)	C31—C30—H30	120.0
N1—C9—C10	118.0 (4)	C32—C31—C30	120.5 (5)
C14—C9—C10	119.0 (4)	C32—C31—H31	119.7
C11—C10—C9	120.0 (4)	C30—C31—H31	119.7
C11—C10—H10	120.0	C33—C32—C31	120.0 (4)
C9—C10—H10	120.0	C33—C32—H32	120.0
C10—C11—C12	121.7 (5)	C31—C32—H32	120.0
C10—C11—H11	119.2	C32—C33—C34	119.6 (5)
C12—C11—H11	119.2	C32—C33—H33	120.2
C13—C12—C11	119.8 (5)	C34—C33—H33	120.2
C13—C12—H12	120.1	C33—C34—C29	121.3 (4)
C11—C12—H12	120.1	C33—C34—H34	119.4
C12—C13—C14	120.7 (5)	C29—C34—H34	119.4
C12—C13—H13	119.6

Experimental details

Crystal data
Chemical formula	C₃₄H₂₂Br₂N₂S·CDCl₃
M_r	770.81
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	10.161 (4), 10.246 (5), 15.868 (6)
α, β, γ (°)	93.88 (3), 99.43 (3), 92.50 (3)
V (Å³)	1623.4 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.84
Crystal size (mm)	0.26 × 0.24 × 0.12

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	Analytical (de Meulenaer & Tompa, 1965)
T_min, T_max	0.489, 0.712
No. of measured, independent and observed [I > 2σ(I)] reflections	5894, 5692, 4210
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.130, 0.84
No. of reflections	5692
No. of parameters	432
No. of restraints	436
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.64

Computer programs: CAD-4 Manual (Schagen et al., 1989), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CrystalMaker (CrystalMaker, 2005).

Acknowledgements

This research was supported by the Australian Research Council.

References

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