4-(5-{2-[5-(4-Cyano­phen­yl)-3-methyl­thio­phen-2-yl]-3,3,4,4,5,5-hexa­fluoro­cyclo­pent-1-en-1-yl}-4-methyl­thio­phen-2-yl)benzo­nitrile chloro­form hemisolvate

El-Hiti, G.A.; Smith, K.; Masmali, A.; Balakit, A.A.; Kariuki, B.M.

doi:10.1107/S1600536813014852

organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1041

https://doi.org/10.1107/S1600536813014852

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4-(5-{2-[5-(4-Cyanophenyl)-3-methylthiophen-2-yl]-3,3,4,4,5,5-hexafluorocyclopent-1-en-1-yl}-4-methylthiophen-2-yl)benzonitrile chloroform hemisolvate

Gamal A. El-Hiti,^a ^* Keith Smith,^b Ali Masmali,^a Asim A. Balakit ^b and Benson M. Kariuki ^b ‡

^aDepartment of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, and ^bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, Wales
^*Correspondence e-mail: gelhiti@ksu.edu.sa

(Received 26 May 2013; accepted 29 May 2013; online 8 June 2013)

The crystal structure of the title compound, C₂₉H₁₆F₆N₂S₂·0.5CHCl₃, consists of molecules with disordered perfluorocyclopentene rings [occupancy ratio 0.685 (3):0.315 (3)] and close F⋯F contacts (in the range 2.45–2.73 Å) between molecules. The short contacts are associated with the disorder. The dihedral angle between thiophene rings is 57.44 (8)°. The 5-(4-cyanophenyl)-3-methyl-2-thienyl groups of adjacent molecules are parallel, leading to zigzag chains of molecules along [101]. The dihedral angles between each thiophene ring and its adjacent cyanobenzene ring are 8.9 (2) and 7.15 (10)°.

Related literature

For applications of substituted thienylperfluorocyclopentenes as switches, see: Waldeck (1991 ); Pu et al. (2006 ); Dulic et al. (2007 ). For related structures, see: Irie et al. (1995 , 2000 ); Morimitsu et al. (2002 ); Mori et al. (2011 ).

Experimental

Crystal data

C₂₉H₁₆F₆N₂S₂·0.5CHCl₃
M_r = 630.24
Monoclinic, C 2/c
a = 18.4237 (4) Å
b = 15.7594 (6) Å
c = 20.9299 (7) Å
β = 113.280 (2)°
V = 5582.2 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 150 K
0.40 × 0.30 × 0.30 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.857, T_max = 0.890
10636 measured reflections
6329 independent reflections
4168 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.174
S = 1.04
6329 reflections
455 parameters
92 restraints
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP99 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813014852/mw2111sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813014852/mw2111Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813014852/mw2111Isup3.cml

checkCIF report

Comment top

During research focused on new synthetic routes towards novel substituted thienylperfluorocyclopentene, we have synthesized and purified the title compound (I). The crystal structure of I contains disordered chloroform solvent located close to a two-fold axis. The perfluorocyclopentene ring is disordered with two components having 68.5 (3)% and 31.5 (3)% occupancy related by a flip between alternative envelope configurations (Figure 2). Unfavourably close F···F contacts with distances in the range 2.45–2.73 Å between pairs of molecules may partly account for the disorder in the ring. The planes of both 5-(4-cyanophenyl)-3-methyl-2-thienyl groups of the molecule are parallel with similar groups of neighbouring molecules, with interplanar distances of 3.39 Å and 3.50 Å, forming zigzag chains parallel to the [101] direction (Figure 2). Stacking of the chains forms planes parallel to the (101) plane.

Related literature top

For applications of substituted thienylperfluorocyclopentenes as switchers, see: Waldeck (1991); Pu et al. (2006); Dulic et al. (2007). For related structures, see: Irie et al. (1995, 2000); Morimitsu et al. (2002); Mori et al. (2011).

Structure description top

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP99 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).

Figures top

	Fig. 1. A molecule of I showing the major component of the disorder with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A segment of the crystal structure of I showing the parallel arrangement of 5-(4-cyanophenyl)-3-methyl-2-thienyl groups with the minor component of the disorder and hydrogen atoms omitted.

4-(5-{2-[5-(4-Cyanophenyl)-3-methylthiophen-2-yl]-3,3,4,4,5,5-hexafluorocyclopent-1-en-1-yl}-4-methylthiophen-2-yl)benzonitrile chloroform hemisolvate top

Crystal data top

C₂₉H₁₆F₆N₂S₂·0.5CHCl₃	F(000) = 2552
M_r = 630.24	D_x = 1.500 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4168 reflections
a = 18.4237 (4) Å	θ = 2.8–27.4°
b = 15.7594 (6) Å	µ = 0.40 mm⁻¹
c = 20.9299 (7) Å	T = 150 K
β = 113.280 (2)°	Block, yellow
V = 5582.2 (3) Å³	0.40 × 0.30 × 0.30 mm
Z = 8

Data collection top

Nonius KappaCCD diffractometer	6329 independent reflections
Radiation source: fine-focus sealed tube	4168 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
CCD slices scans	θ_max = 27.4°, θ_min = 2.8°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −23→23
T_min = 0.857, T_max = 0.890	k = −18→20
10636 measured reflections	l = −27→27

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0749P)² + 7.3013P] where P = (F_o² + 2F_c²)/3
6329 reflections	(Δ/σ)_max = 0.001
455 parameters	Δρ_max = 0.32 e Å⁻³
92 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₂₉H₁₆F₆N₂S₂·0.5CHCl₃	V = 5582.2 (3) Å³
M_r = 630.24	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 18.4237 (4) Å	µ = 0.40 mm⁻¹
b = 15.7594 (6) Å	T = 150 K
c = 20.9299 (7) Å	0.40 × 0.30 × 0.30 mm
β = 113.280 (2)°

Data collection top

Nonius KappaCCD diffractometer	6329 independent reflections
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	4168 reflections with I > 2σ(I)
T_min = 0.857, T_max = 0.890	R_int = 0.042
10636 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	92 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.04	Δρ_max = 0.32 e Å⁻³
6329 reflections	Δρ_min = −0.42 e Å⁻³
455 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	0.33279 (18)	1.2412 (2)	−0.04232 (18)	0.0504 (8)
C2	0.39449 (16)	1.18251 (19)	−0.00118 (17)	0.0445 (7)
C3	0.38411 (18)	1.1334 (2)	0.04903 (19)	0.0572 (9)
H3	0.3372	1.1388	0.0573	0.069*
C4	0.44183 (18)	1.0763 (2)	0.0874 (2)	0.0555 (9)
H4	0.4340	1.0422	0.1215	0.067*
C5	0.51131 (16)	1.06837 (18)	0.07655 (15)	0.0395 (7)
C6	0.52104 (17)	1.11841 (19)	0.02572 (16)	0.0440 (7)
H6	0.5679	1.1131	0.0174	0.053*
C7	0.46373 (17)	1.1756 (2)	−0.01281 (17)	0.0461 (7)
H7	0.4714	1.2099	−0.0470	0.055*
C8	0.57310 (16)	1.00838 (18)	0.11772 (15)	0.0375 (6)
C9	0.64811 (15)	1.00024 (18)	0.12016 (14)	0.0356 (6)
H9	0.6676	1.0340	0.0928	0.043*
C10	0.69445 (15)	0.93707 (17)	0.16712 (15)	0.0357 (6)
C11	0.77772 (17)	0.9166 (2)	0.17704 (17)	0.0457 (7)
H11A	0.8145	0.9497	0.2161	0.069*
H11B	0.7855	0.9309	0.1346	0.069*
H11C	0.7876	0.8560	0.1869	0.069*
C12	0.65256 (16)	0.89691 (18)	0.19993 (15)	0.0379 (6)
C13	0.68037 (16)	0.82944 (18)	0.25213 (16)	0.0405 (7)	0.685 (3)
C14	0.6335 (5)	0.7514 (7)	0.2517 (3)	0.0471 (18)	0.685 (3)
C15	0.6940 (3)	0.6865 (4)	0.2969 (3)	0.0438 (13)	0.685 (3)
C16	0.7615 (4)	0.7421 (5)	0.3474 (3)	0.0413 (15)	0.685 (3)
C17	0.74912 (17)	0.82530 (18)	0.30905 (16)	0.0418 (7)	0.685 (3)
F1	0.5924 (3)	0.7238 (2)	0.1859 (2)	0.0739 (14)	0.685 (3)
F2	0.5788 (2)	0.7682 (2)	0.2782 (3)	0.0744 (11)	0.685 (3)
F3	0.71811 (19)	0.6400 (2)	0.25617 (17)	0.0661 (10)	0.685 (3)
F4	0.6623 (3)	0.6336 (3)	0.3290 (2)	0.0727 (13)	0.685 (3)
F5	0.83090 (19)	0.7038 (2)	0.3585 (2)	0.0710 (11)	0.685 (3)
F6	0.7555 (4)	0.7454 (4)	0.4099 (3)	0.0715 (15)	0.685 (3)
C13A	0.68037 (16)	0.82944 (18)	0.25213 (16)	0.0405 (7)	0.315 (3)
C14A	0.6303 (12)	0.7494 (16)	0.2320 (11)	0.0471 (18)	0.315 (3)
C15A	0.6662 (8)	0.6950 (10)	0.2968 (9)	0.0438 (13)	0.315 (3)
C16A	0.7502 (10)	0.7307 (12)	0.3286 (10)	0.0413 (15)	0.315 (3)
C17A	0.74912 (17)	0.82530 (18)	0.30905 (16)	0.0418 (7)	0.315 (3)
F1A	0.6337 (5)	0.7071 (6)	0.1786 (5)	0.0739 (14)	0.315 (3)
F2A	0.5523 (4)	0.7582 (5)	0.2185 (7)	0.079 (3)	0.315 (3)
F3A	0.6725 (7)	0.6131 (6)	0.2876 (7)	0.107 (4)	0.315 (3)
F4A	0.6312 (5)	0.7076 (7)	0.3410 (4)	0.099 (3)	0.315 (3)
F5A	0.8056 (5)	0.6908 (5)	0.3168 (5)	0.0710 (11)	0.315 (3)
F6A	0.7809 (10)	0.7365 (11)	0.4001 (8)	0.0715 (15)	0.315 (3)
C18	0.80784 (17)	0.89096 (19)	0.33911 (15)	0.0399 (7)
C19	0.79551 (17)	0.97566 (19)	0.34710 (14)	0.0398 (7)
C20	0.71654 (17)	1.0172 (2)	0.33051 (16)	0.0456 (7)
H20A	0.6964	1.0395	0.2829	0.068*
H20B	0.7225	1.0639	0.3632	0.068*
H20C	0.6793	0.9754	0.3346	0.068*
C21	0.86700 (17)	1.0205 (2)	0.37701 (15)	0.0427 (7)
H21	0.8692	1.0796	0.3864	0.051*
C22	0.93311 (18)	0.9721 (2)	0.39144 (15)	0.0444 (7)
C23	1.01629 (18)	0.9987 (2)	0.42181 (15)	0.0448 (7)
C24	1.0359 (2)	1.0850 (2)	0.43260 (18)	0.0566 (9)
H24	0.9945	1.1257	0.4198	0.068*
C25	1.11288 (19)	1.1127 (2)	0.46109 (18)	0.0548 (9)
H25	1.1244	1.1715	0.4679	0.066*
C26	1.17385 (19)	1.0532 (2)	0.47980 (16)	0.0506 (8)
C27	1.15609 (19)	0.9674 (3)	0.46981 (17)	0.0564 (9)
H27	1.1977	0.9270	0.4828	0.068*
C28	1.07840 (19)	0.9403 (2)	0.44115 (17)	0.0529 (8)
H28	1.0671	0.8813	0.4346	0.063*
C29	1.2554 (2)	1.0801 (2)	0.50949 (19)	0.0578 (9)
N1	0.28399 (17)	1.28672 (19)	−0.07370 (17)	0.0657 (9)
N2	1.32050 (18)	1.1008 (2)	0.53249 (18)	0.0706 (9)
S1	0.55727 (4)	0.93605 (5)	0.17304 (4)	0.0422 (2)
S2	0.90768 (5)	0.86753 (5)	0.36945 (4)	0.0485 (2)
C30	0.4976 (5)	1.2497 (5)	0.2286 (6)	0.057 (3)	0.334 (3)
H30	0.4817	1.2508	0.1771	0.068*	0.334 (3)
Cl1	0.4299 (2)	1.1883 (3)	0.2487 (3)	0.0696 (8)	0.334 (3)
Cl2	0.5063 (6)	1.3539 (2)	0.2602 (6)	0.075 (3)	0.334 (3)
Cl3	0.5920 (2)	1.2059 (3)	0.2688 (4)	0.0696 (8)	0.334 (3)
C30A	0.5104 (14)	1.2114 (16)	0.2263 (15)	0.057 (3)	0.166 (3)
H30A	0.5259	1.1925	0.1879	0.068*	0.166 (3)
Cl1A	0.4634 (6)	1.1251 (7)	0.2494 (4)	0.116 (4)	0.166 (3)
Cl2A	0.4406 (6)	1.2868 (9)	0.1950 (5)	0.121 (4)	0.166 (3)
Cl3A	0.5987 (5)	1.2325 (6)	0.3015 (6)	0.0696 (8)	0.166 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0403 (17)	0.0414 (17)	0.059 (2)	0.0019 (13)	0.0083 (15)	0.0036 (16)
C2	0.0359 (15)	0.0356 (15)	0.0499 (18)	0.0013 (12)	0.0039 (13)	−0.0001 (14)
C3	0.0355 (16)	0.057 (2)	0.075 (2)	0.0085 (14)	0.0182 (16)	0.0234 (19)
C4	0.0401 (17)	0.058 (2)	0.069 (2)	0.0099 (14)	0.0219 (16)	0.0233 (18)
C5	0.0324 (14)	0.0359 (15)	0.0403 (16)	−0.0001 (11)	0.0038 (12)	−0.0028 (13)
C6	0.0415 (16)	0.0406 (16)	0.0455 (18)	0.0043 (12)	0.0125 (13)	0.0021 (14)
C7	0.0441 (16)	0.0406 (16)	0.0467 (18)	0.0046 (13)	0.0106 (14)	0.0027 (14)
C8	0.0367 (14)	0.0335 (14)	0.0364 (15)	−0.0012 (11)	0.0082 (12)	0.0001 (12)
C9	0.0353 (14)	0.0338 (14)	0.0334 (15)	−0.0013 (11)	0.0090 (11)	0.0006 (12)
C10	0.0341 (14)	0.0334 (14)	0.0345 (15)	0.0017 (11)	0.0081 (11)	−0.0023 (12)
C11	0.0399 (16)	0.0509 (18)	0.0444 (18)	0.0042 (13)	0.0146 (13)	0.0060 (15)
C12	0.0362 (14)	0.0330 (14)	0.0413 (16)	0.0020 (11)	0.0119 (12)	0.0004 (13)
C13	0.0418 (15)	0.0337 (15)	0.0469 (17)	0.0043 (12)	0.0185 (13)	0.0029 (13)
C14	0.0419 (19)	0.0447 (19)	0.048 (5)	−0.0011 (15)	0.011 (3)	0.005 (4)
C15	0.039 (4)	0.037 (2)	0.056 (2)	0.006 (3)	0.019 (3)	0.0123 (19)
C16	0.050 (3)	0.033 (3)	0.027 (5)	0.003 (2)	0.000 (3)	−0.004 (3)
C17	0.0467 (16)	0.0349 (15)	0.0424 (17)	0.0081 (12)	0.0160 (13)	0.0056 (13)
F1	0.067 (3)	0.0438 (19)	0.0713 (19)	−0.016 (2)	−0.014 (3)	0.0090 (16)
F2	0.0487 (19)	0.067 (2)	0.115 (3)	0.0030 (15)	0.041 (2)	0.021 (2)
F3	0.072 (2)	0.0518 (19)	0.062 (2)	0.0090 (16)	0.0134 (16)	−0.0098 (16)
F4	0.075 (2)	0.061 (3)	0.073 (3)	−0.0102 (19)	0.021 (2)	0.029 (2)
F5	0.050 (2)	0.0415 (15)	0.096 (3)	0.0148 (14)	0.0020 (18)	0.016 (2)
F6	0.113 (5)	0.063 (2)	0.038 (2)	−0.009 (3)	0.0298 (19)	0.0121 (17)
C13A	0.0418 (15)	0.0337 (15)	0.0469 (17)	0.0043 (12)	0.0185 (13)	0.0029 (13)
C14A	0.0419 (19)	0.0447 (19)	0.048 (5)	−0.0011 (15)	0.011 (3)	0.005 (4)
C15A	0.039 (4)	0.037 (2)	0.056 (2)	0.006 (3)	0.019 (3)	0.0123 (19)
C16A	0.050 (3)	0.033 (3)	0.027 (5)	0.003 (2)	0.000 (3)	−0.004 (3)
C17A	0.0467 (16)	0.0349 (15)	0.0424 (17)	0.0081 (12)	0.0160 (13)	0.0056 (13)
F1A	0.067 (3)	0.0438 (19)	0.0713 (19)	−0.016 (2)	−0.014 (3)	0.0090 (16)
F2A	0.054 (4)	0.060 (5)	0.122 (8)	−0.001 (4)	0.033 (5)	0.030 (5)
F3A	0.111 (8)	0.038 (5)	0.130 (10)	−0.001 (4)	0.003 (8)	0.027 (6)
F4A	0.102 (6)	0.114 (8)	0.089 (6)	−0.007 (5)	0.044 (5)	0.047 (6)
F5A	0.050 (2)	0.0415 (15)	0.096 (3)	0.0148 (14)	0.0020 (18)	0.016 (2)
F6A	0.113 (5)	0.063 (2)	0.038 (2)	−0.009 (3)	0.0298 (19)	0.0121 (17)
C18	0.0443 (15)	0.0399 (15)	0.0312 (15)	0.0080 (12)	0.0103 (12)	0.0057 (13)
C19	0.0456 (16)	0.0416 (16)	0.0285 (15)	0.0059 (12)	0.0107 (12)	0.0039 (13)
C20	0.0492 (17)	0.0432 (17)	0.0415 (17)	0.0076 (13)	0.0149 (14)	−0.0022 (14)
C21	0.0492 (17)	0.0408 (16)	0.0345 (16)	0.0019 (13)	0.0127 (13)	−0.0022 (13)
C22	0.0482 (17)	0.0474 (18)	0.0333 (16)	0.0030 (14)	0.0115 (13)	0.0001 (14)
C23	0.0472 (17)	0.0513 (18)	0.0320 (15)	0.0049 (14)	0.0115 (13)	0.0020 (14)
C24	0.0515 (19)	0.060 (2)	0.050 (2)	0.0063 (16)	0.0107 (15)	0.0051 (17)
C25	0.0503 (19)	0.059 (2)	0.049 (2)	−0.0030 (15)	0.0135 (15)	0.0018 (17)
C26	0.0487 (18)	0.072 (2)	0.0309 (16)	−0.0037 (16)	0.0156 (13)	0.0032 (16)
C27	0.0465 (18)	0.078 (3)	0.0416 (19)	0.0094 (17)	0.0141 (15)	0.0068 (18)
C28	0.0550 (19)	0.058 (2)	0.0430 (19)	0.0073 (15)	0.0168 (15)	−0.0004 (16)
C29	0.054 (2)	0.072 (2)	0.050 (2)	0.0061 (17)	0.0234 (17)	0.0149 (18)
N1	0.0491 (16)	0.0540 (18)	0.079 (2)	0.0116 (14)	0.0094 (15)	0.0143 (17)
N2	0.0505 (18)	0.092 (3)	0.069 (2)	−0.0019 (17)	0.0233 (15)	0.0148 (19)
S1	0.0354 (4)	0.0395 (4)	0.0490 (5)	0.0026 (3)	0.0139 (3)	0.0064 (3)
S2	0.0460 (4)	0.0449 (4)	0.0457 (5)	0.0101 (3)	0.0088 (3)	0.0021 (4)
C30	0.036 (5)	0.083 (10)	0.055 (6)	0.003 (7)	0.020 (5)	−0.004 (7)
Cl1	0.0468 (17)	0.075 (2)	0.079 (3)	−0.0058 (11)	0.016 (2)	0.0163 (16)
Cl2	0.100 (4)	0.0733 (19)	0.081 (7)	−0.038 (4)	0.067 (5)	−0.031 (4)
Cl3	0.0468 (17)	0.075 (2)	0.079 (3)	−0.0058 (11)	0.016 (2)	0.0163 (16)
C30A	0.036 (5)	0.083 (10)	0.055 (6)	0.003 (7)	0.020 (5)	−0.004 (7)
Cl1A	0.115 (6)	0.125 (8)	0.080 (5)	−0.071 (6)	0.009 (5)	0.016 (6)
Cl2A	0.086 (6)	0.175 (10)	0.110 (6)	0.069 (7)	0.048 (5)	0.042 (7)
Cl3A	0.0468 (17)	0.075 (2)	0.079 (3)	−0.0058 (11)	0.016 (2)	0.0163 (16)

Geometric parameters (Å, º) top

C1—N1	1.135 (4)	C14A—C15A	1.52 (2)
C1—C2	1.454 (4)	C15A—F3A	1.316 (18)
C2—C3	1.378 (5)	C15A—F4A	1.335 (17)
C2—C7	1.394 (5)	C15A—C16A	1.53 (2)
C3—C4	1.382 (4)	C16A—F5A	1.303 (19)
C3—H3	0.9500	C16A—F6A	1.378 (18)
C4—C5	1.391 (4)	C18—C19	1.375 (4)
C4—H4	0.9500	C18—S2	1.732 (3)
C5—C6	1.392 (4)	C19—C21	1.405 (4)
C5—C8	1.469 (4)	C19—C20	1.506 (4)
C6—C7	1.380 (4)	C20—H20A	0.9800
C6—H6	0.9500	C20—H20B	0.9800
C7—H7	0.9500	C20—H20C	0.9800
C8—C9	1.369 (4)	C21—C22	1.365 (4)
C8—S1	1.730 (3)	C21—H21	0.9500
C9—C10	1.422 (4)	C22—C23	1.469 (4)
C9—H9	0.9500	C22—S2	1.726 (3)
C10—C12	1.374 (4)	C23—C28	1.398 (4)
C10—C11	1.500 (4)	C23—C24	1.402 (5)
C11—H11A	0.9800	C24—C25	1.375 (5)
C11—H11B	0.9800	C24—H24	0.9500
C11—H11C	0.9800	C25—C26	1.395 (5)
C12—C13	1.464 (4)	C25—H25	0.9500
C12—S1	1.732 (3)	C26—C27	1.387 (5)
C13—C17	1.355 (4)	C26—C29	1.444 (5)
C13—C14	1.500 (10)	C27—C28	1.383 (5)
C14—F2	1.355 (7)	C27—H27	0.9500
C14—F1	1.356 (7)	C28—H28	0.9500
C14—C15	1.534 (10)	C29—N2	1.149 (4)
C15—F3	1.327 (6)	C30—Cl3	1.748 (8)
C15—F4	1.341 (6)	C30—Cl2	1.754 (8)
C15—C16	1.547 (8)	C30—Cl1	1.755 (8)
C16—F5	1.349 (7)	C30—H30	1.0000
C16—F6	1.355 (6)	C30A—Cl2A	1.68 (2)
C16—C17	1.507 (8)	C30A—Cl1A	1.78 (3)
C17—C18	1.449 (4)	C30A—Cl3A	1.79 (3)
C14A—F1A	1.32 (2)	C30A—H30A	1.0000
C14A—F2A	1.36 (2)

N1—C1—C2	178.8 (4)	F1A—C14A—C15A	108.6 (18)
C3—C2—C7	120.1 (3)	F2A—C14A—C15A	107.2 (16)
C3—C2—C1	119.8 (3)	F3A—C15A—F4A	110.0 (14)
C7—C2—C1	120.1 (3)	F3A—C15A—C14A	117.1 (17)
C2—C3—C4	120.1 (3)	F4A—C15A—C14A	112.0 (13)
C2—C3—H3	119.9	F3A—C15A—C16A	106.9 (12)
C4—C3—H3	119.9	F4A—C15A—C16A	109.1 (14)
C3—C4—C5	120.7 (3)	C14A—C15A—C16A	100.9 (14)
C3—C4—H4	119.7	F5A—C16A—F6A	102.8 (14)
C5—C4—H4	119.7	F5A—C16A—C15A	118.3 (13)
C4—C5—C6	118.6 (3)	F6A—C16A—C15A	114.0 (18)
C4—C5—C8	120.8 (3)	C19—C18—C17	128.0 (3)
C6—C5—C8	120.6 (3)	C19—C18—S2	111.4 (2)
C7—C6—C5	121.1 (3)	C17—C18—S2	120.6 (2)
C7—C6—H6	119.4	C18—C19—C21	111.8 (3)
C5—C6—H6	119.4	C18—C19—C20	125.8 (3)
C6—C7—C2	119.4 (3)	C21—C19—C20	122.3 (3)
C6—C7—H7	120.3	C19—C20—H20A	109.5
C2—C7—H7	120.3	C19—C20—H20B	109.5
C9—C8—C5	128.3 (3)	H20A—C20—H20B	109.5
C9—C8—S1	110.4 (2)	C19—C20—H20C	109.5
C5—C8—S1	121.4 (2)	H20A—C20—H20C	109.5
C8—C9—C10	114.4 (3)	H20B—C20—H20C	109.5
C8—C9—H9	122.8	C22—C21—C19	114.6 (3)
C10—C9—H9	122.8	C22—C21—H21	122.7
C12—C10—C9	111.4 (2)	C19—C21—H21	122.7
C12—C10—C11	125.3 (3)	C21—C22—C23	128.6 (3)
C9—C10—C11	123.2 (3)	C21—C22—S2	110.4 (2)
C10—C11—H11A	109.5	C23—C22—S2	121.0 (2)
C10—C11—H11B	109.5	C28—C23—C24	117.6 (3)
H11A—C11—H11B	109.5	C28—C23—C22	122.2 (3)
C10—C11—H11C	109.5	C24—C23—C22	120.3 (3)
H11A—C11—H11C	109.5	C25—C24—C23	122.2 (3)
H11B—C11—H11C	109.5	C25—C24—H24	118.9
C10—C12—C13	127.4 (3)	C23—C24—H24	118.9
C10—C12—S1	111.8 (2)	C24—C25—C26	119.1 (3)
C13—C12—S1	120.8 (2)	C24—C25—H25	120.4
C17—C13—C12	128.4 (3)	C26—C25—H25	120.4
C17—C13—C14	107.5 (4)	C27—C26—C25	119.8 (3)
C12—C13—C14	124.0 (4)	C27—C26—C29	119.7 (3)
F2—C14—F1	105.7 (6)	C25—C26—C29	120.5 (3)
F2—C14—C13	111.0 (7)	C28—C27—C26	120.6 (3)
F1—C14—C13	111.0 (6)	C28—C27—H27	119.7
F2—C14—C15	110.7 (6)	C26—C27—H27	119.7
F1—C14—C15	113.0 (7)	C27—C28—C23	120.7 (3)
C13—C14—C15	105.5 (5)	C27—C28—H28	119.7
F3—C15—F4	107.5 (5)	C23—C28—H28	119.7
F3—C15—C14	108.5 (5)	N2—C29—C26	179.0 (5)
F4—C15—C14	111.7 (5)	C8—S1—C12	92.00 (14)
F3—C15—C16	111.7 (4)	C22—S2—C18	91.79 (15)
F4—C15—C16	113.7 (5)	Cl3—C30—Cl2	105.3 (6)
C14—C15—C16	103.6 (5)	Cl3—C30—Cl1	109.4 (5)
F5—C16—F6	106.5 (5)	Cl2—C30—Cl1	113.2 (6)
F5—C16—C17	114.5 (6)	Cl3—C30—H30	109.6
F6—C16—C17	115.4 (5)	Cl2—C30—H30	109.6
F5—C16—C15	108.3 (5)	Cl1—C30—H30	109.6
F6—C16—C15	109.3 (6)	Cl2A—C30A—Cl1A	105.5 (13)
C17—C16—C15	102.6 (4)	Cl2A—C30A—Cl3A	120.0 (16)
C13—C17—C18	128.7 (3)	Cl1A—C30A—Cl3A	105.9 (15)
C13—C17—C16	113.7 (3)	Cl2A—C30A—H30A	108.3
C18—C17—C16	117.4 (3)	Cl1A—C30A—H30A	108.3
F1A—C14A—F2A	106.0 (15)	Cl3A—C30A—H30A	108.3

Experimental details

Crystal data
Chemical formula	C₂₉H₁₆F₆N₂S₂·0.5CHCl₃
M_r	630.24
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	150
a, b, c (Å)	18.4237 (4), 15.7594 (6), 20.9299 (7)
β (°)	113.280 (2)
V (Å³)	5582.2 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.40 × 0.30 × 0.30

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.857, 0.890
No. of measured, independent and observed [I > 2σ(I)] reflections	10636, 6329, 4168
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.174, 1.04
No. of reflections	6329
No. of parameters	455
No. of restraints	92
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.42

Computer programs: COLLECT (Nonius, 2000), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP99 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).

Footnotes

‡Additional correspondence author, e-mail: kariukib@cardiff.ac.uk.

Acknowledgements

The authors would like to extend their appreciation to the Deanship of Scientific Research at King Saud University for its funding for this research through research group project RGP-VPP-239.

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