1-(Thio­phen-2-yl)-N-(4-{(E)-[(thio­phen-2-yl)meth­yl]imino­meth­yl}benzyl­idene)methanamine

Chiririwa, H.; Moss, J.R.; Hendricks, D.; Meijboom, R.

doi:10.1107/S1600536812040809

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3137

doi:10.1107/S1600536812040809

Open

access

1-(Thiophen-2-yl)-N-(4-{(E)-[(thiophen-2-yl)methyl]iminomethyl}benzylidene)methanamine

Haleden Chiririwa,^a ^* John R. Moss,^a Denver Hendricks ^b and Reinout Meijboom ^c

^aDepartment of Chemistry, University of Cape Town, Private Bag, Rondebosch, 7707, South Africa, ^bDivision of Medical Biochemistry, Faculty of Health Sciences, Private Bag X3, Observatory 7935, South Africa, and ^cResearch Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg, PO Box 524 Auckland Park, Johannesburg, 2006, South Africa
^*Correspondence e-mail: harrychiririwa@yahoo.com

(Received 18 September 2012; accepted 27 September 2012; online 20 October 2012)

The title compound C₁₈H₁₆N₂S₂, crystallizes with two independent half-molecules in the asymmetric unit, in one of which the thiophene rings are disordered in a 0.67:0.33 ratio. Each independent molecule lies across a crystallographic centre of symmetry. The dihedral angle between central (half) benzene ring and the thiophene ring is 11.82°.

Related literature

For similar thiophenyldimine-based bridging ligands, see: Chakraborty et al. (1999 ); Haga & Koizumi (1985 ); Chiririwa et al. (2011a ,b ).

Experimental

Crystal data

C₁₈H₁₆N₂S₂
M_r = 324.45
Triclinic, $[P \overline 1]$
a = 8.8517 (3) Å
b = 10.3937 (5) Å
c = 10.5763 (4) Å
α = 63.836 (2)°
β = 69.023 (2)°
γ = 72.394 (2)°
V = 803.22 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 173 K
0.22 × 0.20 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.931, T_max = 0.959
34407 measured reflections
3282 independent reflections
2478 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.125
S = 1.06
3282 reflections
206 parameters
9 restraints
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus and XPREP (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ), ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812040809/go2071sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812040809/go2071Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812040809/go2071Isup3.cml

checkCIF report

Comment top

The title compound belongs to a class of tetradentate ligands. To the best of our knowledge, this is the second example of a neutral thiophenyldimine-based bridging ligand, the first of which was reported earlier by our group (Chiririwa et al., 2011a) and (Chiririwa et al., 2011b). This compound is expected to chelate in a tetradentate manner with both nitrogen atoms coordinating along with the two thiophenyl sulphur atoms. Chakraborty et al. reported coordination of similar ligands to ruthenium (Chakraborty et al. 1999) whilst Haga and Kiozumi reported their coordination to molybednum, (Haga & Koizumi,1985). The bond lengths N1A—C6A = 1.265 (3)and N1B—C6B = 1.266 (3) Å are consistent with C=N double bonding.

Related literature top

For similar thiophenyldimine-based bridging ligands, see: Chakraborty et al. (1999); Haga & Koizumi(1985); Chiririwa et al. (2011a,b).

Experimental top

A solution of benzene 1,4-dicarboxaldehyde (0.50 g, 3.73 mmol) in methanol (10 ml) was added dropwise to a stirred solution of 2-thiophenylmethylamine (1.20 g, 7.42 mmol) in methanol (10 ml). The mixture stirred at room temperature for ca 16 h. The precipitate was filtered off and washed with diethylether and dried under vacuum for 4 h affording a white powder in 85% yield. Crystals suitable for X-ray determination were obtained by recrystallization from CH₂Cl₂– hexane mixture at room temperature.: Calc. for C₁₈H₁₆N₂S₂: C, 66.63%; H, 4.97%; N, 8.63%; S, 19.77 Found: C, 66.59%; H, 4.62%; N, 8.72%; S, 19.65 1H NMR: (400 MHz) ?H 8.38 (t, 2H, J = 1.3 Hz) 7.82 (s, 2H) 7.25 (m, 4H) 7.00 (d, 4H, J = 3.4 Hz) 5.00 (d, 4H, J = 1.3 Hz. IR (KBr): 1612 cm-1 (C=N, imine)

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus and XPREP (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005), ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The structure of the (1,4-phenylenebis(methan-1-yl-1-ylidene)) bis(1-(thiophen-2-yl)methanamine) showing 40% probability displacement ellipsoids. Hydrogen atoms were omitted for clarity.

1-(Thiophen-2-yl)-N-(4-{(E)-[(thiophen-2- yl)methyl]iminomethyl}benzylidene)methanamine top

Crystal data top

C₁₈H₁₆N₂S₂	Z = 2
M_r = 324.45	F(000) = 340
Triclinic, P1	D_x = 1.341 Mg m⁻³
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8517 (3) Å	Cell parameters from 34407 reflections
b = 10.3937 (5) Å	θ = 2.9–26.4°
c = 10.5763 (4) Å	µ = 0.33 mm⁻¹
α = 63.836 (2)°	T = 173 K
β = 69.023 (2)°	Plate, colourless
γ = 72.394 (2)°	0.22 × 0.20 × 0.13 mm
V = 803.22 (6) Å³

Data collection top

Nonius KappaCCD diffractometer	3282 independent reflections
Radiation source: fine-focus sealed tube	2478 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
1.2° ϕ scans and ω scans	θ_max = 26.4°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = 0→11
T_min = 0.931, T_max = 0.959	k = −11→13
34407 measured reflections	l = −11→13

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) = 0.125	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.056P)² + 0.4946P] where P = (F_o² + 2F_c²)/3
3282 reflections	(Δ/σ)_max < 0.001
206 parameters	Δρ_max = 0.34 e Å⁻³
9 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₁₈H₁₆N₂S₂	γ = 72.394 (2)°
M_r = 324.45	V = 803.22 (6) Å³
Triclinic, P1	Z = 2
a = 8.8517 (3) Å	Mo Kα radiation
b = 10.3937 (5) Å	µ = 0.33 mm⁻¹
c = 10.5763 (4) Å	T = 173 K
α = 63.836 (2)°	0.22 × 0.20 × 0.13 mm
β = 69.023 (2)°

Data collection top

Nonius KappaCCD diffractometer	3282 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2478 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.959	R_int = 0.052
34407 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	9 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.06	Δρ_max = 0.34 e Å⁻³
3282 reflections	Δρ_min = −0.48 e Å⁻³
206 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1A	0.69140 (9)	−0.07229 (9)	0.71753 (8)	0.0551 (3)
N1A	0.8877 (2)	0.1968 (2)	0.4771 (2)	0.0338 (5)
C1A	0.4849 (3)	−0.0628 (3)	0.7957 (3)	0.0479 (7)
H1A	0.4372	−0.1242	0.8918	0.058*
C2A	0.3981 (3)	0.0419 (3)	0.7047 (3)	0.0431 (6)
H2A	0.2815	0.0627	0.7295	0.052*
C3A	0.4989 (3)	0.1187 (3)	0.5671 (3)	0.0383 (6)
H3A	0.4571	0.1966	0.4905	0.046*
C4A	0.6632 (3)	0.0676 (3)	0.5574 (3)	0.0322 (5)
C5A	0.8063 (3)	0.1240 (3)	0.4339 (3)	0.0352 (6)
H5A1	0.8850	0.0425	0.4092	0.042*
H5A2	0.7678	0.1938	0.3465	0.042*
C6A	0.8751 (3)	0.3337 (3)	0.4146 (3)	0.0312 (5)
H6A	0.8204	0.3833	0.3389	0.037*
C7A	0.9431 (3)	0.4184 (2)	0.4562 (2)	0.0284 (5)
C8A	1.0455 (3)	0.3496 (3)	0.5499 (3)	0.0327 (5)
H8A	1.0777	0.2468	0.5838	0.039*
C9A	0.8997 (3)	0.5696 (3)	0.4064 (3)	0.0334 (5)
H9A	0.8313	0.6177	0.3413	0.040*
N1B	0.1122 (2)	0.6222 (2)	1.0089 (2)	0.0352 (5)
C4B	0.3208 (3)	0.4419 (2)	0.9269 (3)	0.0335 (5)
C5B	0.1887 (3)	0.4689 (3)	1.0535 (3)	0.0366 (6)
H5B1	0.1048	0.4074	1.0881	0.044*
H5B2	0.2367	0.4426	1.1349	0.044*
C6B	0.1358 (3)	0.6967 (3)	1.0657 (3)	0.0324 (5)
H6B	0.2009	0.6504	1.1335	0.039*
C7B	0.0661 (3)	0.8528 (3)	1.0305 (3)	0.0316 (5)
C8B	−0.0294 (3)	0.9267 (3)	0.9307 (3)	0.0327 (5)
H8B	−0.0496	0.8767	0.8833	0.039*
C9B	0.0946 (3)	0.9276 (3)	1.0991 (3)	0.0332 (5)
H9B	0.1595	0.8779	1.1670	0.040*
S1B1	0.34911 (15)	0.29538 (12)	0.88477 (13)	0.0351 (3)	0.67
C1B1	0.5072 (4)	0.3432 (3)	0.7441 (3)	0.0555 (8)
H1B1	0.5647	0.2863	0.6858	0.067*
C2B1	0.5492 (3)	0.4673 (3)	0.7172 (3)	0.0534 (8)
H2B1	0.6371	0.5103	0.6402	0.064*
C3B1	0.4387 (8)	0.5249 (7)	0.8248 (6)	0.0351 (3)	0.67
H3B1	0.4460	0.6137	0.8260	0.042*	0.67
S1B2	0.4503 (4)	0.5553 (3)	0.8214 (4)	0.0443 (7)	0.33
C3B2	0.3679 (13)	0.3308 (11)	0.8727 (12)	0.0443 (7)	0.33
H3B2	0.3115	0.2505	0.9179	0.053*	0.33

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.0367 (4)	0.0570 (5)	0.0504 (5)	−0.0094 (3)	−0.0160 (3)	0.0026 (4)
N1A	0.0311 (11)	0.0349 (11)	0.0371 (11)	−0.0090 (9)	−0.0081 (9)	−0.0134 (9)
C1A	0.0417 (15)	0.0519 (17)	0.0424 (16)	−0.0179 (13)	−0.0059 (12)	−0.0085 (13)
C2A	0.0320 (13)	0.0457 (15)	0.0534 (17)	−0.0068 (11)	−0.0105 (12)	−0.0204 (13)
C3A	0.0357 (13)	0.0390 (14)	0.0441 (15)	−0.0068 (11)	−0.0132 (11)	−0.0167 (12)
C4A	0.0354 (13)	0.0311 (12)	0.0367 (13)	−0.0079 (10)	−0.0115 (10)	−0.0155 (10)
C5A	0.0368 (13)	0.0357 (13)	0.0384 (14)	−0.0084 (11)	−0.0099 (11)	−0.0171 (11)
C6A	0.0295 (12)	0.0350 (13)	0.0275 (12)	−0.0078 (10)	−0.0066 (9)	−0.0097 (10)
C7A	0.0260 (11)	0.0302 (12)	0.0252 (11)	−0.0086 (9)	−0.0034 (9)	−0.0073 (9)
C8A	0.0319 (12)	0.0281 (12)	0.0344 (13)	−0.0068 (10)	−0.0098 (10)	−0.0064 (10)
C9A	0.0324 (12)	0.0332 (13)	0.0317 (13)	−0.0070 (10)	−0.0135 (10)	−0.0049 (10)
N1B	0.0316 (11)	0.0335 (11)	0.0402 (12)	−0.0020 (9)	−0.0094 (9)	−0.0160 (9)
C4B	0.0346 (13)	0.0326 (13)	0.0354 (13)	−0.0008 (10)	−0.0162 (10)	−0.0123 (10)
C5B	0.0391 (14)	0.0308 (12)	0.0384 (14)	−0.0037 (10)	−0.0112 (11)	−0.0125 (11)
C6B	0.0275 (12)	0.0340 (13)	0.0324 (13)	−0.0038 (10)	−0.0063 (10)	−0.0118 (10)
C7B	0.0252 (11)	0.0348 (13)	0.0322 (13)	−0.0048 (10)	−0.0033 (9)	−0.0137 (10)
C8B	0.0313 (12)	0.0356 (13)	0.0330 (13)	−0.0078 (10)	−0.0049 (10)	−0.0158 (10)
C9B	0.0287 (12)	0.0367 (13)	0.0328 (13)	−0.0047 (10)	−0.0079 (10)	−0.0126 (10)
S1B1	0.0441 (6)	0.0294 (6)	0.0375 (5)	−0.0095 (4)	−0.0131 (4)	−0.0136 (5)
C1B1	0.0624 (19)	0.0591 (19)	0.0555 (19)	0.0135 (15)	−0.0272 (16)	−0.0368 (16)
C2B1	0.0373 (15)	0.067 (2)	0.0419 (16)	−0.0066 (14)	−0.0023 (12)	−0.0158 (14)
C3B1	0.0441 (6)	0.0294 (6)	0.0375 (5)	−0.0095 (4)	−0.0131 (4)	−0.0136 (5)
S1B2	0.0408 (12)	0.0379 (16)	0.0556 (13)	−0.0146 (10)	−0.0074 (10)	−0.0177 (11)
C3B2	0.0408 (12)	0.0379 (16)	0.0556 (13)	−0.0146 (10)	−0.0074 (10)	−0.0177 (11)

Geometric parameters (Å, º) top

S1A—C1A	1.708 (3)	C4B—C3B2	1.399 (5)
S1A—C4A	1.719 (3)	C4B—C5B	1.500 (3)
N1A—C6A	1.265 (3)	C4B—S1B2	1.640 (3)
N1A—C5A	1.473 (3)	C4B—S1B1	1.694 (2)
C1A—C2A	1.342 (4)	C5B—H5B1	0.9900
C1A—H1A	0.9500	C5B—H5B2	0.9900
C2A—C3A	1.424 (4)	C6B—C7B	1.476 (3)
C2A—H2A	0.9500	C6B—H6B	0.9500
C3A—C4A	1.372 (3)	C7B—C9B	1.394 (3)
C3A—H3A	0.9500	C7B—C8B	1.396 (3)
C4A—C5A	1.498 (3)	C8B—C9Bⁱⁱ	1.381 (3)
C5A—H5A1	0.9900	C8B—H8B	0.9500
C5A—H5A2	0.9900	C9B—C8Bⁱⁱ	1.381 (3)
C6A—C7A	1.478 (3)	C9B—H9B	0.9500
C6A—H6A	0.9500	S1B1—C1B1	1.642 (3)
C7A—C8A	1.394 (3)	C1B1—C2B1	1.332 (3)
C7A—C9A	1.394 (3)	C1B1—C3B2	1.459 (5)
C8A—C9Aⁱ	1.380 (3)	C1B1—H1B1	0.9500
C8A—H8A	0.9500	C2B1—C3B1	1.435 (5)
C9A—C8Aⁱ	1.380 (3)	C2B1—S1B2	1.591 (3)
C9A—H9A	0.9500	C2B1—H2B1	0.9500
N1B—C6B	1.266 (3)	C3B1—H3B1	0.9500
N1B—C5B	1.461 (3)	C3B2—H3B2	0.9500
C4B—C3B1	1.384 (5)

C1A—S1A—C4A	92.37 (13)	C5B—C4B—S1B1	123.56 (17)
C6A—N1A—C5A	117.3 (2)	S1B2—C4B—S1B1	115.94 (16)
C2A—C1A—S1A	111.7 (2)	N1B—C5B—C4B	109.8 (2)
C2A—C1A—H1A	124.1	N1B—C5B—H5B1	109.7
S1A—C1A—H1A	124.1	C4B—C5B—H5B1	109.7
C1A—C2A—C3A	113.0 (2)	N1B—C5B—H5B2	109.7
C1A—C2A—H2A	123.5	C4B—C5B—H5B2	109.7
C3A—C2A—H2A	123.5	H5B1—C5B—H5B2	108.2
C4A—C3A—C2A	112.4 (2)	N1B—C6B—C7B	122.5 (2)
C4A—C3A—H3A	123.8	N1B—C6B—H6B	118.8
C2A—C3A—H3A	123.8	C7B—C6B—H6B	118.8
C3A—C4A—C5A	128.2 (2)	C9B—C7B—C8B	119.3 (2)
C3A—C4A—S1A	110.46 (19)	C9B—C7B—C6B	119.5 (2)
C5A—C4A—S1A	121.24 (18)	C8B—C7B—C6B	121.2 (2)
N1A—C5A—C4A	109.30 (19)	C9Bⁱⁱ—C8B—C7B	120.0 (2)
N1A—C5A—H5A1	109.8	C9Bⁱⁱ—C8B—H8B	120.0
C4A—C5A—H5A1	109.8	C7B—C8B—H8B	120.0
N1A—C5A—H5A2	109.8	C8Bⁱⁱ—C9B—C7B	120.7 (2)
C4A—C5A—H5A2	109.8	C8Bⁱⁱ—C9B—H9B	119.7
H5A1—C5A—H5A2	108.3	C7B—C9B—H9B	119.7
N1A—C6A—C7A	121.8 (2)	C1B1—S1B1—C4B	94.00 (13)
N1A—C6A—H6A	119.1	C2B1—C1B1—C3B2	102.2 (3)
C7A—C6A—H6A	119.1	C2B1—C1B1—S1B1	115.4 (2)
C8A—C7A—C9A	118.8 (2)	C2B1—C1B1—H1B1	122.3
C8A—C7A—C6A	121.2 (2)	C3B2—C1B1—H1B1	135.5
C9A—C7A—C6A	120.0 (2)	S1B1—C1B1—H1B1	122.3
C9Aⁱ—C8A—C7A	120.2 (2)	C1B1—C2B1—C3B1	108.1 (3)
C9Aⁱ—C8A—H8A	119.9	C1B1—C2B1—S1B2	119.7 (2)
C7A—C8A—H8A	119.9	C1B1—C2B1—H2B1	126.0
C8Aⁱ—C9A—C7A	121.1 (2)	C3B1—C2B1—H2B1	126.0
C8Aⁱ—C9A—H9A	119.5	S1B2—C2B1—H2B1	114.3
C7A—C9A—H9A	119.5	C4B—C3B1—C2B1	115.3 (4)
C6B—N1B—C5B	116.7 (2)	C4B—C3B1—H3B1	122.3
C3B1—C4B—C3B2	97.2 (4)	C2B1—C3B1—H3B1	122.3
C3B1—C4B—C5B	129.2 (3)	C2B1—S1B2—C4B	94.97 (16)
C3B2—C4B—C5B	133.6 (3)	C4B—C3B2—C1B1	117.2 (5)
C3B2—C4B—S1B2	105.9 (3)	C4B—C3B2—H3B2	121.4
C5B—C4B—S1B2	120.50 (18)	C1B1—C3B2—H3B2	121.4
C3B1—C4B—S1B1	107.2 (3)

C4A—S1A—C1A—C2A	−0.1 (2)	C3B1—C4B—S1B1—C1B1	0.7 (4)
S1A—C1A—C2A—C3A	−0.2 (3)	C3B2—C4B—S1B1—C1B1	−2 (4)
C1A—C2A—C3A—C4A	0.5 (3)	C5B—C4B—S1B1—C1B1	−179.4 (2)
C2A—C3A—C4A—C5A	−177.0 (2)	S1B2—C4B—S1B1—C1B1	−0.5 (2)
C2A—C3A—C4A—S1A	−0.6 (3)	C4B—S1B1—C1B1—C2B1	−0.5 (3)
C1A—S1A—C4A—C3A	0.4 (2)	C4B—S1B1—C1B1—C3B2	2 (3)
C1A—S1A—C4A—C5A	177.1 (2)	C3B2—C1B1—C2B1—C3B1	−0.3 (9)
C6A—N1A—C5A—C4A	−110.5 (2)	S1B1—C1B1—C2B1—C3B1	0.2 (5)
C3A—C4A—C5A—N1A	108.5 (3)	C3B2—C1B1—C2B1—S1B2	0.9 (7)
S1A—C4A—C5A—N1A	−67.7 (2)	S1B1—C1B1—C2B1—S1B2	1.5 (4)
C5A—N1A—C6A—C7A	176.1 (2)	C3B2—C4B—C3B1—C2B1	−0.2 (8)
N1A—C6A—C7A—C8A	10.0 (3)	C5B—C4B—C3B1—C2B1	179.4 (3)
N1A—C6A—C7A—C9A	−167.3 (2)	S1B2—C4B—C3B1—C2B1	172 (4)
C9A—C7A—C8A—C9Aⁱ	0.9 (4)	S1B1—C4B—C3B1—C2B1	−0.7 (7)
C6A—C7A—C8A—C9Aⁱ	−176.4 (2)	C1B1—C2B1—C3B1—C4B	0.4 (7)
C8A—C7A—C9A—C8Aⁱ	−0.9 (4)	S1B2—C2B1—C3B1—C4B	−174 (3)
C6A—C7A—C9A—C8Aⁱ	176.4 (2)	C1B1—C2B1—S1B2—C4B	−1.5 (4)
C6B—N1B—C5B—C4B	−112.6 (2)	C3B1—C2B1—S1B2—C4B	4 (2)
C3B1—C4B—C5B—N1B	42.8 (6)	C3B1—C4B—S1B2—C2B1	−6 (3)
C3B2—C4B—C5B—N1B	−137.8 (9)	C3B2—C4B—S1B2—C2B1	1.4 (8)
S1B2—C4B—C5B—N1B	44.0 (3)	C5B—C4B—S1B2—C2B1	−179.9 (2)
S1B1—C4B—C5B—N1B	−137.1 (2)	S1B1—C4B—S1B2—C2B1	1.1 (3)
C5B—N1B—C6B—C7B	179.9 (2)	C3B1—C4B—C3B2—C1B1	−0.1 (11)
N1B—C6B—C7B—C9B	178.8 (2)	C5B—C4B—C3B2—C1B1	−179.6 (5)
N1B—C6B—C7B—C8B	−0.5 (4)	S1B2—C4B—C3B2—C1B1	−1.2 (13)
C9B—C7B—C8B—C9Bⁱⁱ	0.0 (4)	S1B1—C4B—C3B2—C1B1	177 (5)
C6B—C7B—C8B—C9Bⁱⁱ	179.3 (2)	C2B1—C1B1—C3B2—C4B	0.3 (12)
C8B—C7B—C9B—C8Bⁱⁱ	0.0 (4)	S1B1—C1B1—C3B2—C4B	−178 (4)
C6B—C7B—C9B—C8Bⁱⁱ	−179.3 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂S₂
M_r	324.45
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.8517 (3), 10.3937 (5), 10.5763 (4)
α, β, γ (°)	63.836 (2), 69.023 (2), 72.394 (2)
V (Å³)	803.22 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.22 × 0.20 × 0.13

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.931, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	34407, 3282, 2478
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.125, 1.06
No. of reflections	3282
No. of parameters	206
No. of restraints	9
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.48

Computer programs: APEX2 (Bruker, 2007), SAINT-Plus (Bruker, 2007), SAINT-Plus and XPREP (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Acknowledgements

Mintek and Project AuTEK are acknowledged for funding this project.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chakraborty, S., Munshi, P. & Lahiri, G. K. (1999). Polyhedron, 18, 1437–1444. Web of Science CrossRef CAS Google Scholar
Chiririwa, H., Meijboom, R. & Omondi, B. (2011b). Acta Cryst. E67, o922. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chiririwa, H., Moss, J. R., Su, H., Hendricks, D. & Meijboom, R. (2011a). Acta Cryst. E67, o921. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Haga, M. & Koizumi, K. (1985). Inorg. Chim. Acta, 104, 47–50. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.