organic compounds
1-(Thiophen-2-yl)-N-(4-{(E)-[(thiophen-2-yl)methyl]iminomethyl}benzylidene)methanamine
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
The title compound C18H16N2S2, crystallizes with two independent half-molecules in the 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
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Data collection: APEX2 (Bruker, 2007); cell 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
10.1107/S1600536812040809/go2071sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812040809/go2071Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812040809/go2071Isup3.cml
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)
The methine and aromatic H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for aromatic, C—H = 0.99 Å and Uiso(H) = 1.2Ueq(C) for CH2 C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for CH. Disorder
models were applied to the thiophenes of one independent molecule in the Geometrical (FLAT) restaraints were applied to keep the ring C1B1-C2B2-C3B1-C3B2-S1B1-S1B2 planar. Bond distance (DFIX) and 1,3 distance similarity restraints (SADI) were applied to obtain reasonable geometries. Ellipsoid displacement (SIMU and DELU) restraints were also applied to the disordered moieties. Free variables were connected to the disordered component to add to unity.Data collection: APEX2 (Bruker, 2007); cell
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).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. |
C18H16N2S2 | Z = 2 |
Mr = 324.45 | F(000) = 340 |
Triclinic, P1 | Dx = 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 |
Nonius KappaCCD diffractometer | 3282 independent reflections |
Radiation source: fine-focus sealed tube | 2478 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
1.2° ϕ scans and ω scans | θmax = 26.4°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = 0→11 |
Tmin = 0.931, Tmax = 0.959 | k = −11→13 |
34407 measured reflections | l = −11→13 |
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(Fo2) + (0.056P)2 + 0.4946P] where P = (Fo2 + 2Fc2)/3 |
3282 reflections | (Δ/σ)max < 0.001 |
206 parameters | Δρmax = 0.34 e Å−3 |
9 restraints | Δρmin = −0.48 e Å−3 |
C18H16N2S2 | γ = 72.394 (2)° |
Mr = 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)° |
Nonius KappaCCD diffractometer | 3282 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 2478 reflections with I > 2σ(I) |
Tmin = 0.931, Tmax = 0.959 | Rint = 0.052 |
34407 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 9 restraints |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.34 e Å−3 |
3282 reflections | Δρmin = −0.48 e Å−3 |
206 parameters |
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. |
x | y | z | Uiso*/Ueq | 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 |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.931, 0.959 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 34407, 3282, 2478 |
Rint | 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 |
Δρmax, Δρmin (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
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Bruker (2007). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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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.