Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055079/ez2104sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055079/ez2104Isup2.hkl |
CCDC reference: 672881
To a stirred acetone solution (75 ml) of cyclohexylcarbonyl chloride (2.0 g, 14 mmol) and ammoniumthiocyanate (1.04 g, 14 mmol), aniline (1.27 g, 14 mmol) in 40 ml of acetone was added dropwise. The reaction mixture was refluxed for 1 h. The resulting solution was poured into a beaker containing some ice blocks. The white precipitate was filtered off and washed with distilled water and cold ethanol before drying under vacuum. Good quality crystals were obtained by recrystallization from methanol.
After their location in a difference map, all H-atoms were fixed geometrically at ideal positions and allowed to ride on the parent C or N atoms with C—H = 0.93–0.97 Å and N—H = 0.86 Å with Uiso(H)= 1.2 (CH2 and NH).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C14H18N2OS | Z = 2 |
Mr = 262.36 | F(000) = 280 |
Triclinic, P1 | Dx = 1.268 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.696 (2) Å | Cell parameters from 837 reflections |
b = 9.395 (3) Å | θ = 1.7–25.4° |
c = 12.578 (4) Å | µ = 0.23 mm−1 |
α = 100.262 (5)° | T = 293 K |
β = 104.720 (5)° | Block, colourless |
γ = 110.075 (5)° | 0.46 × 0.42 × 0.22 mm |
V = 687.4 (4) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 2547 independent reflections |
Radiation source: fine-focus sealed tube | 2207 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.4°, θmin = 1.7° |
ω scan | h = −8→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −11→11 |
Tmin = 0.903, Tmax = 0.952 | l = −15→15 |
6848 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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0459P)2 + 0.1063P] where P = (Fo2 + 2Fc2)/3 |
2547 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C14H18N2OS | γ = 110.075 (5)° |
Mr = 262.36 | V = 687.4 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.696 (2) Å | Mo Kα radiation |
b = 9.395 (3) Å | µ = 0.23 mm−1 |
c = 12.578 (4) Å | T = 293 K |
α = 100.262 (5)° | 0.46 × 0.42 × 0.22 mm |
β = 104.720 (5)° |
Bruker SMART APEX CCD area-detector diffractometer | 2547 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2207 reflections with I > 2σ(I) |
Tmin = 0.903, Tmax = 0.952 | Rint = 0.019 |
6848 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.18 e Å−3 |
2547 reflections | Δρmin = −0.17 e Å−3 |
163 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 | ||
S1 | 0.34074 (6) | 0.15250 (5) | 0.11564 (3) | 0.05336 (15) | |
N2 | 0.56387 (19) | 0.24546 (14) | −0.02447 (10) | 0.0459 (3) | |
H2A | 0.5697 | 0.2301 | −0.0929 | 0.055* | |
O1 | 0.37126 (19) | 0.08767 (14) | −0.24588 (9) | 0.0631 (3) | |
N1 | 0.21478 (19) | 0.03681 (14) | −0.10875 (10) | 0.0458 (3) | |
H1A | 0.0942 | −0.0228 | −0.0995 | 0.055* | |
C9 | 0.7521 (2) | 0.37186 (16) | 0.06468 (12) | 0.0414 (3) | |
C7 | 0.2163 (2) | 0.00689 (17) | −0.21976 (12) | 0.0462 (3) | |
C6 | 0.0093 (2) | −0.13047 (17) | −0.30580 (12) | 0.0457 (3) | |
H6A | −0.0568 | −0.2029 | −0.2647 | 0.055* | |
C8 | 0.3803 (2) | 0.14953 (16) | −0.01007 (12) | 0.0416 (3) | |
C10 | 0.7245 (3) | 0.49819 (19) | 0.12396 (14) | 0.0541 (4) | |
H10A | 0.5819 | 0.4995 | 0.1082 | 0.065* | |
C14 | 0.9628 (2) | 0.37063 (18) | 0.08647 (13) | 0.0477 (4) | |
H14A | 0.9818 | 0.2867 | 0.0452 | 0.057* | |
C13 | 1.1471 (3) | 0.4958 (2) | 0.17066 (14) | 0.0583 (4) | |
H13A | 1.2899 | 0.4946 | 0.1868 | 0.070* | |
C1 | 0.0713 (3) | −0.2208 (2) | −0.39591 (14) | 0.0575 (4) | |
H1B | 0.1462 | −0.1492 | −0.4341 | 0.069* | |
H1C | 0.1759 | −0.2618 | −0.3587 | 0.069* | |
C12 | 1.1208 (3) | 0.6209 (2) | 0.23018 (14) | 0.0620 (5) | |
H12A | 1.2451 | 0.7047 | 0.2863 | 0.074* | |
C3 | −0.3147 (3) | −0.3017 (2) | −0.53876 (14) | 0.0632 (5) | |
H3A | −0.4496 | −0.3927 | −0.5901 | 0.076* | |
H3B | −0.2580 | −0.2347 | −0.5842 | 0.076* | |
C5 | −0.1659 (3) | −0.07249 (19) | −0.36170 (14) | 0.0531 (4) | |
H5A | −0.1008 | 0.0042 | −0.3992 | 0.064* | |
H5B | −0.2087 | −0.0203 | −0.3031 | 0.064* | |
C11 | 0.9092 (3) | 0.6221 (2) | 0.20657 (15) | 0.0622 (4) | |
H11A | 0.8910 | 0.7073 | 0.2467 | 0.075* | |
C2 | −0.1381 (3) | −0.3573 (2) | −0.48445 (15) | 0.0637 (5) | |
H2B | −0.0954 | −0.4078 | −0.5438 | 0.076* | |
H2C | −0.2018 | −0.4354 | −0.4477 | 0.076* | |
C4 | −0.3753 (3) | −0.2105 (2) | −0.44985 (15) | 0.0643 (5) | |
H4A | −0.4496 | −0.2811 | −0.4109 | 0.077* | |
H4B | −0.4805 | −0.1703 | −0.4877 | 0.077* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0464 (2) | 0.0612 (3) | 0.0426 (2) | 0.01045 (19) | 0.01690 (17) | 0.01272 (18) |
N2 | 0.0388 (6) | 0.0484 (7) | 0.0397 (6) | 0.0069 (5) | 0.0138 (5) | 0.0089 (5) |
O1 | 0.0529 (7) | 0.0675 (7) | 0.0465 (6) | −0.0014 (6) | 0.0184 (5) | 0.0149 (5) |
N1 | 0.0371 (6) | 0.0461 (7) | 0.0422 (7) | 0.0046 (5) | 0.0134 (5) | 0.0106 (5) |
C9 | 0.0378 (7) | 0.0429 (7) | 0.0387 (7) | 0.0104 (6) | 0.0127 (6) | 0.0134 (6) |
C7 | 0.0425 (8) | 0.0467 (8) | 0.0431 (8) | 0.0113 (7) | 0.0133 (6) | 0.0147 (7) |
C6 | 0.0430 (8) | 0.0441 (8) | 0.0409 (8) | 0.0078 (6) | 0.0130 (6) | 0.0130 (6) |
C8 | 0.0364 (7) | 0.0404 (7) | 0.0449 (8) | 0.0135 (6) | 0.0119 (6) | 0.0124 (6) |
C10 | 0.0436 (8) | 0.0550 (9) | 0.0583 (10) | 0.0184 (7) | 0.0157 (7) | 0.0098 (8) |
C14 | 0.0431 (8) | 0.0511 (8) | 0.0514 (9) | 0.0188 (7) | 0.0180 (7) | 0.0189 (7) |
C13 | 0.0370 (8) | 0.0733 (11) | 0.0570 (10) | 0.0152 (8) | 0.0113 (7) | 0.0226 (9) |
C1 | 0.0529 (9) | 0.0603 (10) | 0.0541 (10) | 0.0231 (8) | 0.0147 (8) | 0.0095 (8) |
C12 | 0.0498 (10) | 0.0605 (10) | 0.0476 (9) | 0.0013 (8) | 0.0061 (7) | 0.0085 (8) |
C3 | 0.0563 (10) | 0.0647 (11) | 0.0449 (9) | 0.0105 (8) | 0.0059 (7) | 0.0061 (8) |
C5 | 0.0474 (9) | 0.0518 (9) | 0.0525 (9) | 0.0155 (7) | 0.0153 (7) | 0.0099 (7) |
C11 | 0.0659 (11) | 0.0517 (9) | 0.0569 (10) | 0.0164 (8) | 0.0202 (9) | 0.0041 (8) |
C2 | 0.0690 (11) | 0.0554 (10) | 0.0544 (10) | 0.0208 (9) | 0.0164 (8) | 0.0035 (8) |
C4 | 0.0448 (9) | 0.0695 (11) | 0.0622 (11) | 0.0168 (8) | 0.0078 (8) | 0.0091 (9) |
S1—C8 | 1.6653 (15) | C13—H13A | 0.9300 |
N2—C8 | 1.3292 (18) | C1—C2 | 1.521 (2) |
N2—C9 | 1.4268 (17) | C1—H1B | 0.9700 |
N2—H2A | 0.8600 | C1—H1C | 0.9700 |
O1—C7 | 1.2172 (17) | C12—C11 | 1.376 (3) |
N1—C7 | 1.3777 (19) | C12—H12A | 0.9300 |
N1—C8 | 1.3846 (18) | C3—C2 | 1.509 (3) |
N1—H1A | 0.8600 | C3—C4 | 1.509 (2) |
C9—C14 | 1.372 (2) | C3—H3A | 0.9700 |
C9—C10 | 1.380 (2) | C3—H3B | 0.9700 |
C7—C6 | 1.507 (2) | C5—C4 | 1.525 (2) |
C6—C1 | 1.522 (2) | C5—H5A | 0.9700 |
C6—C5 | 1.524 (2) | C5—H5B | 0.9700 |
C6—H6A | 0.9800 | C11—H11A | 0.9300 |
C10—C11 | 1.376 (2) | C2—H2B | 0.9700 |
C10—H10A | 0.9300 | C2—H2C | 0.9700 |
C14—C13 | 1.387 (2) | C4—H4A | 0.9700 |
C14—H14A | 0.9300 | C4—H4B | 0.9700 |
C13—C12 | 1.367 (3) | ||
C8—N2—C9 | 125.13 (12) | C2—C1—H1C | 109.4 |
C8—N2—H2A | 117.4 | C6—C1—H1C | 109.4 |
C9—N2—H2A | 117.4 | H1B—C1—H1C | 108.0 |
C7—N1—C8 | 129.00 (12) | C13—C12—C11 | 119.65 (15) |
C7—N1—H1A | 115.5 | C13—C12—H12A | 120.2 |
C8—N1—H1A | 115.5 | C11—C12—H12A | 120.2 |
C14—C9—C10 | 120.34 (14) | C2—C3—C4 | 111.90 (14) |
C14—C9—N2 | 119.24 (13) | C2—C3—H3A | 109.2 |
C10—C9—N2 | 120.33 (13) | C4—C3—H3A | 109.2 |
O1—C7—N1 | 122.25 (13) | C2—C3—H3B | 109.2 |
O1—C7—C6 | 123.07 (13) | C4—C3—H3B | 109.2 |
N1—C7—C6 | 114.66 (12) | H3A—C3—H3B | 107.9 |
C7—C6—C1 | 110.87 (13) | C6—C5—C4 | 110.71 (13) |
C7—C6—C5 | 110.31 (12) | C6—C5—H5A | 109.5 |
C1—C6—C5 | 111.02 (13) | C4—C5—H5A | 109.5 |
C7—C6—H6A | 108.2 | C6—C5—H5B | 109.5 |
C1—C6—H6A | 108.2 | C4—C5—H5B | 109.5 |
C5—C6—H6A | 108.2 | H5A—C5—H5B | 108.1 |
N2—C8—N1 | 115.78 (13) | C10—C11—C12 | 120.41 (16) |
N2—C8—S1 | 125.19 (11) | C10—C11—H11A | 119.8 |
N1—C8—S1 | 119.00 (10) | C12—C11—H11A | 119.8 |
C11—C10—C9 | 119.65 (15) | C3—C2—C1 | 111.72 (14) |
C11—C10—H10A | 120.2 | C3—C2—H2B | 109.3 |
C9—C10—H10A | 120.2 | C1—C2—H2B | 109.3 |
C9—C14—C13 | 119.36 (15) | C3—C2—H2C | 109.3 |
C9—C14—H14A | 120.3 | C1—C2—H2C | 109.3 |
C13—C14—H14A | 120.3 | H2B—C2—H2C | 107.9 |
C12—C13—C14 | 120.57 (15) | C3—C4—C5 | 111.35 (14) |
C12—C13—H13A | 119.7 | C3—C4—H4A | 109.4 |
C14—C13—H13A | 119.7 | C5—C4—H4A | 109.4 |
C2—C1—C6 | 110.98 (14) | C3—C4—H4B | 109.4 |
C2—C1—H1B | 109.4 | C5—C4—H4B | 109.4 |
C6—C1—H1B | 109.4 | H4A—C4—H4B | 108.0 |
C8—N2—C9—C14 | 120.74 (16) | C10—C9—C14—C13 | 1.6 (2) |
C8—N2—C9—C10 | −62.8 (2) | N2—C9—C14—C13 | 178.01 (13) |
C8—N1—C7—O1 | −3.9 (2) | C9—C14—C13—C12 | −1.2 (2) |
C8—N1—C7—C6 | 177.58 (13) | C7—C6—C1—C2 | −178.70 (13) |
O1—C7—C6—C1 | 37.5 (2) | C5—C6—C1—C2 | −55.71 (18) |
N1—C7—C6—C1 | −143.95 (14) | C14—C13—C12—C11 | 0.2 (3) |
O1—C7—C6—C5 | −85.88 (18) | C7—C6—C5—C4 | 179.44 (13) |
N1—C7—C6—C5 | 92.65 (15) | C1—C6—C5—C4 | 56.13 (18) |
C9—N2—C8—N1 | 178.47 (12) | C9—C10—C11—C12 | 0.1 (3) |
C9—N2—C8—S1 | −3.4 (2) | C13—C12—C11—C10 | 0.3 (3) |
C7—N1—C8—N2 | 2.1 (2) | C4—C3—C2—C1 | −54.5 (2) |
C7—N1—C8—S1 | −176.13 (12) | C6—C1—C2—C3 | 54.8 (2) |
C14—C9—C10—C11 | −1.0 (2) | C2—C3—C4—C5 | 54.9 (2) |
N2—C9—C10—C11 | −177.45 (14) | C6—C5—C4—C3 | −55.56 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.95 | 2.6471 (18) | 137 |
N1—H1A···S1i | 0.86 | 2.68 | 3.4997 (19) | 160 |
Symmetry code: (i) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C14H18N2OS |
Mr | 262.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 6.696 (2), 9.395 (3), 12.578 (4) |
α, β, γ (°) | 100.262 (5), 104.720 (5), 110.075 (5) |
V (Å3) | 687.4 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.46 × 0.42 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.903, 0.952 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6848, 2547, 2207 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.604 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.092, 1.07 |
No. of reflections | 2547 |
No. of parameters | 163 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.17 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.95 | 2.6471 (18) | 137 |
N1—H1A···S1i | 0.86 | 2.68 | 3.4997 (19) | 160 |
Symmetry code: (i) −x, −y, −z. |
Thiourea derivatives have received considerable attention because of their potential applications in materials science (Wei et al., 2004) and their biological activities (Baruah et al., 2002). The title compound, (I), is similar to N-benzoyl-N'-phenylthiourea (II) (Yamin & Yusof, 2003), except that one of the phenyl groups is replaced by a cyclohexane group (Fig. 1). The molecule maintains its trans-cis configuration with respect to the positions of the cyclohexylcarbonyl and phenyl groups relative to the thiono S1 atom across the two C—N bonds. The bond lengths and angles are in normal ranges and comparable to those in (II) and other thiourea derivatives (Yusof et al., 2007). The central carbonylthiourea (S1/N1/N2/C7/O1/C8) fragment and phenyl ring (C9—C14) are all planar, with a maximum deviation of 0.038 (1) Å from the least-squares plane for atom N1. The central carbonylthiourea fragment makes a dihedral angle of 62.68 (6)° with the phenyl ring, which is larger than the equivalent dihedral angle in (II) (28.78 (9)°).
There is an intramolecular hydrogen bond, N2—H2A···O1 (Table 1), which results in a pseudo-six-membered ring, O1···H2A—N2—C8—N1—C7—O1. In the crystal structure, the molecules are linked by two equivalent N—H···S intermolecular interactions, (symmetry codes as in Table 1) to form dimers (Fig. 2).