organic compounds
1-Cyclohexylmethyl-3-methyl-2-[(phenylimino)(sulfido)methyl]benzimidazolium
aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, Faculty of Arts and Sciences, Ínönü University, 44280 Malatya, Turkey, cDepartment of Chemistry, Faculty of Arts and Sciences, Adıyaman University, 02040 Adıyaman, Turkey, and dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr
In the zwitterionic title compound, C22H25N3S, the benzimidazole ring system makes a dihedral angle of 55.69 (11)° with the phenyl ring. In the inter- and intramolecular C—H⋯S interactions occur.
Related literature
For related structures, see: Öztürk et al. (2004); Akkurt et al. (2005). For background, see: Allen et al. (1987); Cremer & Pople (1975); Küçükbay et al. (1995); Winberg & Coffman (1965).
Experimental
Crystal data
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Refinement
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Data collection: X-AREA (Stoe & Cie, 2002); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536808008842/hb2714sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008842/hb2714Isup2.hkl
Phenyl isothiocyanate (0.7 ml, 5. 86 mmol) was added to a solution of bis(1-cyclohexylmethyl-3-methylbenzimidazolidine-2-ylidene) (1.1 g, 2.41 mmol) in toluene (15 ml) and the mixture was stirred at room temperature for 2 h. A yellow solid was precipitated in solution. The precipitate was filtered and recrystallized in EtOH / DMF to yield yellow blocks of (I). (Yield: 1.49 g, 85%. m.p.:463–465 K). 1H NMR (DMSO-d6,δ, p.p.m.): 1.11 (s, ring methylene, 6H), 1.59 (d, ring methylene, 4H), 2.09 (s, ring methylene, 1H), 4.04 (s, CH3, 3H), 4.45 (d, –CH2—N, 2H), 7.22 (m, Ar—H (forPhNCS), 5H), 7.93 (m, Ar—H, 4H); 13C NMR (DMSO-d6, δ,p.p.m.): 25.10, 25.15, 30.05, 30.12,38.05, 50.03, 112.11, 122.04, 122.10, 126.01, 129.03, 129.14, 131.23, 149.06,151.34, 167.44. Analysis calculated for C22H25N3S: C 72.72, H 6.88, N 11.57, S 8.81%; found: C 71.82, H 6.87, N 11.46, S 8.22%.
All H atoms were placed in calculated positions and refined as riding with C—H = 0.93–0.97 Å and Uiso(H) = 1.2 or 1.5Ueq(C).
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).C22H25N3S | F(000) = 776 |
Mr = 363.52 | Dx = 1.177 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 12543 reflections |
a = 11.0999 (8) Å | θ = 1.4–28.0° |
b = 12.4601 (7) Å | µ = 0.17 mm−1 |
c = 15.0143 (14) Å | T = 296 K |
β = 99.007 (7)° | Block, yellow |
V = 2051.0 (3) Å3 | 0.62 × 0.56 × 0.51 mm |
Z = 4 |
Stoe IPDSII diffractometer | 3997 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2727 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.031 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.9° |
ω scans | h = −13→13 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −15→13 |
Tmin = 0.903, Tmax = 0.919 | l = −18→18 |
11769 measured reflections |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0746P)2] where P = (Fo2 + 2Fc2)/3 |
3997 reflections | (Δ/σ)max < 0.001 |
236 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
C22H25N3S | V = 2051.0 (3) Å3 |
Mr = 363.52 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.0999 (8) Å | µ = 0.17 mm−1 |
b = 12.4601 (7) Å | T = 296 K |
c = 15.0143 (14) Å | 0.62 × 0.56 × 0.51 mm |
β = 99.007 (7)° |
Stoe IPDSII diffractometer | 3997 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2727 reflections with I > 2σ(I) |
Tmin = 0.903, Tmax = 0.919 | Rint = 0.031 |
11769 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.36 e Å−3 |
3997 reflections | Δρmin = −0.37 e Å−3 |
236 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
S1 | 0.40319 (5) | 0.79425 (5) | 0.26689 (5) | 0.0886 (2) | |
N1 | 0.28968 (12) | 0.63297 (12) | 0.44357 (9) | 0.0502 (5) | |
N2 | 0.34915 (12) | 0.54355 (11) | 0.33351 (9) | 0.0487 (4) | |
N3 | 0.16469 (13) | 0.75498 (13) | 0.28359 (10) | 0.0572 (5) | |
C1 | 0.32300 (14) | 0.53150 (14) | 0.47690 (11) | 0.0503 (6) | |
C2 | 0.32500 (17) | 0.48719 (19) | 0.56177 (13) | 0.0650 (7) | |
C3 | 0.36543 (19) | 0.3831 (2) | 0.57255 (16) | 0.0738 (8) | |
C4 | 0.40346 (18) | 0.32577 (18) | 0.50294 (17) | 0.0738 (8) | |
C5 | 0.40103 (17) | 0.36931 (16) | 0.41825 (15) | 0.0632 (7) | |
C6 | 0.36035 (14) | 0.47437 (14) | 0.40713 (12) | 0.0494 (5) | |
C7 | 0.30640 (14) | 0.63806 (14) | 0.35726 (11) | 0.0465 (5) | |
C8 | 0.2483 (2) | 0.72060 (18) | 0.49579 (14) | 0.0687 (7) | |
C9 | 0.27958 (15) | 0.73442 (14) | 0.29906 (11) | 0.0507 (5) | |
C10 | 0.11976 (17) | 0.84557 (17) | 0.23179 (13) | 0.0614 (6) | |
C11 | 0.1515 (2) | 0.94910 (19) | 0.25693 (16) | 0.0791 (8) | |
C12 | 0.0936 (3) | 1.0351 (2) | 0.2082 (2) | 0.1043 (11) | |
C13 | 0.0082 (3) | 1.0155 (4) | 0.1341 (3) | 0.1179 (14) | |
C14 | −0.0228 (3) | 0.9139 (4) | 0.1091 (2) | 0.1084 (13) | |
C15 | 0.03093 (19) | 0.8291 (2) | 0.15829 (15) | 0.0815 (9) | |
C16 | 0.38428 (16) | 0.51876 (17) | 0.24565 (12) | 0.0577 (6) | |
C17 | 0.27793 (17) | 0.49794 (17) | 0.17240 (12) | 0.0612 (7) | |
C18 | 0.3246 (2) | 0.4812 (2) | 0.08393 (14) | 0.0816 (9) | |
C19 | 0.2221 (3) | 0.4596 (3) | 0.00661 (17) | 0.1112 (15) | |
C20 | 0.1411 (3) | 0.3698 (3) | 0.02668 (19) | 0.1048 (11) | |
C21 | 0.0958 (3) | 0.3852 (3) | 0.1148 (2) | 0.1050 (11) | |
C22 | 0.2009 (2) | 0.4028 (2) | 0.19119 (16) | 0.0819 (9) | |
H2 | 0.30040 | 0.52580 | 0.60880 | 0.0780* | |
H3 | 0.36730 | 0.35010 | 0.62830 | 0.0890* | |
H4 | 0.43140 | 0.25590 | 0.51360 | 0.0890* | |
H5 | 0.42530 | 0.33040 | 0.37130 | 0.0760* | |
H8A | 0.25970 | 0.78770 | 0.46680 | 0.0830* | |
H8B | 0.29450 | 0.72060 | 0.55540 | 0.0830* | |
H8C | 0.16330 | 0.71110 | 0.49940 | 0.0830* | |
H11 | 0.21140 | 0.96190 | 0.30640 | 0.0950* | |
H12 | 0.11300 | 1.10520 | 0.22600 | 0.1250* | |
H13 | −0.02890 | 1.07270 | 0.10060 | 0.1410* | |
H14 | −0.08080 | 0.90140 | 0.05830 | 0.1300* | |
H15 | 0.00700 | 0.75950 | 0.14170 | 0.0980* | |
H16A | 0.43660 | 0.45600 | 0.25200 | 0.0690* | |
H16B | 0.43130 | 0.57830 | 0.22750 | 0.0690* | |
H17 | 0.22580 | 0.56180 | 0.16650 | 0.0730* | |
H18A | 0.38080 | 0.42110 | 0.08990 | 0.0980* | |
H18B | 0.36900 | 0.54460 | 0.07030 | 0.0980* | |
H19A | 0.17360 | 0.52420 | −0.00590 | 0.1330* | |
H19B | 0.25680 | 0.44200 | −0.04700 | 0.1330* | |
H20A | 0.18580 | 0.30280 | 0.02830 | 0.1260* | |
H20B | 0.07190 | 0.36490 | −0.02140 | 0.1260* | |
H21A | 0.04980 | 0.32240 | 0.12770 | 0.1260* | |
H21B | 0.04160 | 0.44660 | 0.11050 | 0.1260* | |
H22A | 0.16900 | 0.41490 | 0.24690 | 0.0980* | |
H22B | 0.25140 | 0.33890 | 0.19880 | 0.0980* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0631 (3) | 0.0819 (4) | 0.1212 (5) | −0.0041 (3) | 0.0155 (3) | 0.0461 (4) |
N1 | 0.0531 (7) | 0.0518 (9) | 0.0451 (8) | −0.0037 (6) | 0.0063 (6) | 0.0022 (7) |
N2 | 0.0498 (7) | 0.0496 (8) | 0.0461 (8) | 0.0028 (6) | 0.0061 (6) | 0.0030 (6) |
N3 | 0.0568 (8) | 0.0579 (9) | 0.0562 (9) | 0.0096 (7) | 0.0069 (7) | 0.0065 (7) |
C1 | 0.0478 (8) | 0.0543 (11) | 0.0468 (10) | −0.0099 (7) | 0.0015 (7) | 0.0064 (8) |
C2 | 0.0643 (11) | 0.0787 (14) | 0.0501 (11) | −0.0184 (10) | 0.0035 (8) | 0.0113 (10) |
C3 | 0.0692 (12) | 0.0802 (16) | 0.0676 (13) | −0.0205 (11) | −0.0033 (10) | 0.0307 (12) |
C4 | 0.0626 (11) | 0.0596 (12) | 0.0941 (17) | −0.0073 (9) | −0.0038 (11) | 0.0271 (12) |
C5 | 0.0598 (10) | 0.0516 (11) | 0.0762 (13) | −0.0010 (8) | 0.0049 (9) | 0.0094 (10) |
C6 | 0.0446 (8) | 0.0500 (10) | 0.0515 (10) | −0.0047 (7) | 0.0008 (7) | 0.0094 (8) |
C7 | 0.0443 (8) | 0.0503 (10) | 0.0441 (9) | −0.0025 (7) | 0.0047 (6) | 0.0023 (7) |
C8 | 0.0832 (13) | 0.0683 (14) | 0.0568 (11) | 0.0026 (10) | 0.0175 (9) | −0.0095 (10) |
C9 | 0.0565 (9) | 0.0501 (10) | 0.0443 (9) | 0.0013 (7) | 0.0044 (7) | 0.0030 (8) |
C10 | 0.0633 (10) | 0.0690 (13) | 0.0535 (10) | 0.0197 (9) | 0.0143 (8) | 0.0077 (10) |
C11 | 0.1043 (16) | 0.0682 (15) | 0.0667 (13) | 0.0194 (12) | 0.0196 (12) | 0.0080 (11) |
C12 | 0.133 (2) | 0.0744 (17) | 0.117 (2) | 0.0412 (16) | 0.055 (2) | 0.0263 (16) |
C13 | 0.110 (2) | 0.147 (3) | 0.104 (2) | 0.073 (2) | 0.0394 (18) | 0.062 (2) |
C14 | 0.0856 (17) | 0.159 (3) | 0.0791 (17) | 0.052 (2) | 0.0083 (13) | 0.029 (2) |
C15 | 0.0686 (12) | 0.1101 (19) | 0.0644 (13) | 0.0266 (12) | 0.0061 (10) | 0.0061 (13) |
C16 | 0.0604 (10) | 0.0609 (12) | 0.0541 (10) | 0.0051 (8) | 0.0165 (8) | 0.0017 (9) |
C17 | 0.0694 (11) | 0.0609 (12) | 0.0528 (11) | 0.0152 (9) | 0.0077 (8) | −0.0019 (9) |
C18 | 0.1018 (16) | 0.0905 (17) | 0.0537 (12) | 0.0079 (13) | 0.0156 (11) | 0.0038 (12) |
C19 | 0.141 (3) | 0.133 (3) | 0.0545 (14) | 0.023 (2) | −0.0003 (15) | 0.0003 (15) |
C20 | 0.114 (2) | 0.105 (2) | 0.0840 (18) | 0.0193 (17) | −0.0204 (16) | −0.0297 (16) |
C21 | 0.0878 (16) | 0.127 (2) | 0.0957 (19) | −0.0097 (15) | 0.0007 (14) | −0.0336 (18) |
C22 | 0.0780 (14) | 0.0992 (18) | 0.0685 (14) | −0.0149 (12) | 0.0116 (11) | −0.0101 (13) |
S1—C9 | 1.6968 (18) | C20—C21 | 1.500 (4) |
N1—C1 | 1.388 (2) | C21—C22 | 1.518 (4) |
N1—C7 | 1.339 (2) | C2—H2 | 0.9300 |
N1—C8 | 1.460 (3) | C3—H3 | 0.9300 |
N2—C6 | 1.392 (2) | C4—H4 | 0.9300 |
N2—C7 | 1.339 (2) | C5—H5 | 0.9300 |
N2—C16 | 1.466 (2) | C8—H8A | 0.9600 |
N3—C9 | 1.286 (2) | C8—H8B | 0.9600 |
N3—C10 | 1.416 (3) | C8—H8C | 0.9600 |
C1—C2 | 1.386 (3) | C11—H11 | 0.9300 |
C1—C6 | 1.383 (2) | C12—H12 | 0.9300 |
C2—C3 | 1.374 (3) | C13—H13 | 0.9300 |
C3—C4 | 1.385 (3) | C14—H14 | 0.9300 |
C4—C5 | 1.379 (3) | C15—H15 | 0.9300 |
C5—C6 | 1.386 (3) | C16—H16A | 0.9700 |
C7—C9 | 1.487 (2) | C16—H16B | 0.9700 |
C10—C11 | 1.374 (3) | C17—H17 | 0.9800 |
C10—C15 | 1.375 (3) | C18—H18A | 0.9700 |
C11—C12 | 1.396 (4) | C18—H18B | 0.9700 |
C12—C13 | 1.366 (5) | C19—H19A | 0.9700 |
C13—C14 | 1.350 (7) | C19—H19B | 0.9700 |
C14—C15 | 1.371 (5) | C20—H20A | 0.9700 |
C16—C17 | 1.505 (3) | C20—H20B | 0.9700 |
C17—C18 | 1.514 (3) | C21—H21A | 0.9700 |
C17—C22 | 1.514 (3) | C21—H21B | 0.9700 |
C18—C19 | 1.517 (4) | C22—H22A | 0.9700 |
C19—C20 | 1.495 (5) | C22—H22B | 0.9700 |
C1—N1—C7 | 108.81 (14) | N1—C8—H8B | 110.00 |
C1—N1—C8 | 125.17 (14) | N1—C8—H8C | 109.00 |
C7—N1—C8 | 125.97 (15) | H8A—C8—H8B | 110.00 |
C6—N2—C7 | 108.94 (14) | H8A—C8—H8C | 109.00 |
C6—N2—C16 | 125.52 (15) | H8B—C8—H8C | 109.00 |
C7—N2—C16 | 125.48 (15) | C10—C11—H11 | 120.00 |
C9—N3—C10 | 120.80 (16) | C12—C11—H11 | 120.00 |
N1—C1—C2 | 131.24 (17) | C11—C12—H12 | 120.00 |
N1—C1—C6 | 106.88 (14) | C13—C12—H12 | 120.00 |
C2—C1—C6 | 121.87 (17) | C12—C13—H13 | 120.00 |
C1—C2—C3 | 116.26 (19) | C14—C13—H13 | 120.00 |
C2—C3—C4 | 122.0 (2) | C13—C14—H14 | 120.00 |
C3—C4—C5 | 121.9 (2) | C15—C14—H14 | 120.00 |
C4—C5—C6 | 116.21 (19) | C10—C15—H15 | 120.00 |
N2—C6—C1 | 106.42 (15) | C14—C15—H15 | 120.00 |
N2—C6—C5 | 131.86 (17) | N2—C16—H16A | 109.00 |
C1—C6—C5 | 121.70 (17) | N2—C16—H16B | 109.00 |
N1—C7—N2 | 108.95 (15) | C17—C16—H16A | 109.00 |
N1—C7—C9 | 124.16 (15) | C17—C16—H16B | 109.00 |
N2—C7—C9 | 126.89 (15) | H16A—C16—H16B | 108.00 |
S1—C9—N3 | 133.19 (14) | C16—C17—H17 | 108.00 |
S1—C9—C7 | 115.18 (12) | C18—C17—H17 | 108.00 |
N3—C9—C7 | 111.63 (15) | C22—C17—H17 | 108.00 |
N3—C10—C11 | 122.96 (18) | C17—C18—H18A | 109.00 |
N3—C10—C15 | 117.92 (19) | C17—C18—H18B | 109.00 |
C11—C10—C15 | 118.8 (2) | C19—C18—H18A | 109.00 |
C10—C11—C12 | 120.0 (2) | C19—C18—H18B | 109.00 |
C11—C12—C13 | 119.6 (3) | H18A—C18—H18B | 108.00 |
C12—C13—C14 | 120.6 (4) | C18—C19—H19A | 109.00 |
C13—C14—C15 | 120.2 (3) | C18—C19—H19B | 109.00 |
C10—C15—C14 | 120.9 (3) | C20—C19—H19A | 109.00 |
N2—C16—C17 | 113.91 (15) | C20—C19—H19B | 109.00 |
C16—C17—C18 | 109.15 (16) | H19A—C19—H19B | 108.00 |
C16—C17—C22 | 113.59 (17) | C19—C20—H20A | 109.00 |
C18—C17—C22 | 109.66 (18) | C19—C20—H20B | 109.00 |
C17—C18—C19 | 112.2 (2) | C21—C20—H20A | 109.00 |
C18—C19—C20 | 112.4 (2) | C21—C20—H20B | 109.00 |
C19—C20—C21 | 112.2 (3) | H20A—C20—H20B | 108.00 |
C20—C21—C22 | 111.2 (3) | C20—C21—H21A | 109.00 |
C17—C22—C21 | 111.2 (2) | C20—C21—H21B | 109.00 |
C1—C2—H2 | 122.00 | C22—C21—H21A | 109.00 |
C3—C2—H2 | 122.00 | C22—C21—H21B | 109.00 |
C2—C3—H3 | 119.00 | H21A—C21—H21B | 108.00 |
C4—C3—H3 | 119.00 | C17—C22—H22A | 109.00 |
C3—C4—H4 | 119.00 | C17—C22—H22B | 109.00 |
C5—C4—H4 | 119.00 | C21—C22—H22A | 109.00 |
C4—C5—H5 | 122.00 | C21—C22—H22B | 109.00 |
C6—C5—H5 | 122.00 | H22A—C22—H22B | 108.00 |
N1—C8—H8A | 109.00 | ||
C7—N1—C1—C2 | 178.50 (18) | C1—C2—C3—C4 | 0.7 (3) |
C8—N1—C1—C2 | 0.9 (3) | C2—C3—C4—C5 | −1.1 (3) |
C7—N1—C1—C6 | −0.28 (18) | C3—C4—C5—C6 | 1.1 (3) |
C8—N1—C1—C6 | −177.88 (16) | C4—C5—C6—C1 | −0.8 (3) |
C1—N1—C7—N2 | 0.09 (19) | C4—C5—C6—N2 | 177.97 (18) |
C8—N1—C7—N2 | 177.66 (16) | N2—C7—C9—N3 | 112.86 (19) |
C1—N1—C7—C9 | 179.56 (15) | N1—C7—C9—S1 | 113.46 (16) |
C8—N1—C7—C9 | −2.9 (3) | N1—C7—C9—N3 | −66.5 (2) |
C6—N2—C7—N1 | 0.14 (18) | N2—C7—C9—S1 | −67.2 (2) |
C16—N2—C7—N1 | −177.02 (15) | N3—C10—C11—C12 | −172.9 (2) |
C6—N2—C7—C9 | −179.31 (15) | C11—C10—C15—C14 | 1.9 (3) |
C16—N2—C7—C9 | 3.5 (3) | C15—C10—C11—C12 | 0.2 (3) |
C6—N2—C16—C17 | 105.6 (2) | N3—C10—C15—C14 | 175.3 (2) |
C7—N2—C16—C17 | −77.7 (2) | C10—C11—C12—C13 | −2.0 (4) |
C7—N2—C6—C5 | −179.20 (18) | C11—C12—C13—C14 | 1.7 (5) |
C7—N2—C6—C1 | −0.31 (18) | C12—C13—C14—C15 | 0.3 (5) |
C16—N2—C6—C1 | 176.85 (15) | C13—C14—C15—C10 | −2.2 (4) |
C16—N2—C6—C5 | −2.0 (3) | N2—C16—C17—C18 | 176.01 (17) |
C9—N3—C10—C11 | −61.4 (3) | N2—C16—C17—C22 | −61.3 (2) |
C9—N3—C10—C15 | 125.6 (2) | C16—C17—C18—C19 | 180.0 (2) |
C10—N3—C9—S1 | −2.0 (3) | C22—C17—C18—C19 | 54.9 (3) |
C10—N3—C9—C7 | 178.02 (15) | C16—C17—C22—C21 | −179.6 (2) |
N1—C1—C6—N2 | 0.36 (18) | C18—C17—C22—C21 | −57.1 (3) |
C6—C1—C2—C3 | −0.4 (3) | C17—C18—C19—C20 | −52.9 (3) |
N1—C1—C2—C3 | −179.03 (18) | C18—C19—C20—C21 | 52.0 (4) |
N1—C1—C6—C5 | 179.38 (16) | C19—C20—C21—C22 | −54.1 (4) |
C2—C1—C6—N2 | −178.56 (16) | C20—C21—C22—C17 | 57.1 (3) |
C2—C1—C6—C5 | 0.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···S1i | 0.97 | 2.73 | 3.683 (2) | 167 |
C16—H16B···S1 | 0.97 | 2.78 | 3.451 (2) | 127 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C22H25N3S |
Mr | 363.52 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 11.0999 (8), 12.4601 (7), 15.0143 (14) |
β (°) | 99.007 (7) |
V (Å3) | 2051.0 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.17 |
Crystal size (mm) | 0.62 × 0.56 × 0.51 |
Data collection | |
Diffractometer | Stoe IPDSII diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.903, 0.919 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11769, 3997, 2727 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.127, 1.02 |
No. of reflections | 3997 |
No. of parameters | 236 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.36, −0.37 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···S1i | 0.97 | 2.73 | 3.683 (2) | 167 |
C16—H16B···S1 | 0.97 | 2.78 | 3.451 (2) | 127 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
Acknowledgements
The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund). HK and NŞ also thank the İnönü University Research Fund (BAPB-2007–46) for financial support of this study.
References
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Electron-rich olefins are exteremly reactive, powerful π-bases, which are readily converted by aryl isothiocyanates to stable yellow-colored mercapto-N-arylformimidoylimidazolinium orbenzimidazolinium inner salts (zwitterions) in high yield (Winberg & Coffman, 1965; Küçükbay et al., 1995). As part of our onging studies of such materials (Öztürk et al., 2004; Akkurt et al., 2005), we now report the synthesis and structure of the title compound, (I).
The S1—C9 formal single bond of length of 1.6968 (18) Å in (I) is comparable to those reported for similar structures (Öztürk et al., 2004; Akkurt et al., 2005). Otherwise the bond lengths and angles in (I) are normal (Allen et al., 1987). The benzimidazole ring system (N1/N2/C1–C7) is almost planar, with maximum deviations of -0.012 (2) Å for C1 and C6, and makes a dihedral angle of 55.69 (11)° with the phenyl ring (C10–C15). The cyclohexane ring system (C17–C22) has a normal chair conformation [puckering parameters (Cremer & Pople, 1975) are QT = 0.554 (3) Å, θ = 175.9 (3)°, ϕ = 136 (4)°].
In the crystal of (I), the molecules display inter- and intramolecular C—H···S interactions (Table 1, Fig. 2).