Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024403/fj2031sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024403/fj2031Isup2.hkl |
CCDC reference: 651508
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.052
- wR factor = 0.147
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound (I), was synthesized by mixing cyclohexanone (0.98 g, 0.01 mol) and o-methoxycyanoacetanilide (1.94 g, 0.01 mol) and refluxing for 1 h (Gewald et al., 1966) in the presence of 4.0 ml of diethylamine. Sulfur powder (1.28 g, 0.04 mol) and 40 ml e thanol were then added, and the resulting solution was heated for 2 h at 323 K. Crystals of (I) were grown by slow evaporation from a solution in 2-propanol (yield 68%).
H atoms were positioned geometrically [N—H = 0.86 Å, and C—H = 0.93 (CH), 0.97 (CH2) and 0.96 Å (CH3)] and constrained to ride on their parent atoms with Uiso(H) values of 1.2 Ueq(C,N), or 1.5 Ueq(C-methyl). A rotating-group model was used for the methyl group.
The title compound (I) is one of a series of 3-aryl carboximides. These compounds display different biological activities, such as antitubercular, antibacterial and antifungal activities (Mohan & Saravanan 2003). Schiff bases containing sulfur are the most effective (Csaszar & Morvay 1983; Lakshmi et al., 1985; Cohen et al.,1977).
The molecular structure and the packing diagram of (I) are shown in Figures (1) and (2) respectively. The thiophene ring is essentially planar, with a short C8—C9 bond distance [1.352 (3) Å,], indicating the absence of delocalization in the double bonds. This is also reflected in the S1—C2 and S1—C8 distances, which are shorter than the normal C—S distances. The cyclohexene ring adopts a half-chair conformation, with the puckering parameters q2 = 0.325 (2) Å, Φ = -99.4 (3)° and θ = 130.7 (2)°. (Cremer & Pople, 1975; Spek, 2003). The thiophene ring makes a dihedral angle of 12.9 (1) ° with the o-methoxyphenyl ring.
The molecular structure of (I) is stabilized by intramolecular C—H···O and N—H···O hydrogen bonds and by intermolecular N—H···O interactions. (Table 2) The intramolecular C16—H16···O1 and N1—H1···O1 hydrogen bonds form pseudo-six membered rings and N2—H2···O2 forms a pseudo five membered ring, thus locking the molecular conformation and eliminating flexibility. Molecules are linked via N—H···O interactions, forming zigzag chains along the c axis, (Fig. 2).
For related literature, see: Cremer & Pople (1975); Lakshmi et al. (1985); Mohan & Saravanan (2003); Spek (2003).
For related literature, see: Cohen et al. (1977); Csaszar & Morvay (1983); Gewald et al. (1966); Sheldrick (1996).
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST (Nardelli, 1995); PLATON (Spek, 2003).
C16H18N2O2S | F(000) = 640 |
Mr = 302.38 | Dx = 1.324 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 520 reflections |
a = 8.709 (2) Å | θ = 1.5–28.5° |
b = 8.576 (2) Å | µ = 0.22 mm−1 |
c = 20.306 (5) Å | T = 293 K |
β = 90.742 (4)° | Prism, colourless |
V = 1516.6 (6) Å3 | 0.48 × 0.25 × 0.04 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2831 independent reflections |
Radiation source: fine-focus sealed tube | 2266 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ψ and ω scans | θmax = 25.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→9 |
Tmin = 0.937, Tmax = 0.998 | k = −10→10 |
10964 measured reflections | l = −24→24 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0762P)2 + 0.3763P] where P = (Fo2 + 2Fc2)/3 |
2831 reflections | (Δ/σ)max < 0.001 |
191 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C16H18N2O2S | V = 1516.6 (6) Å3 |
Mr = 302.38 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.709 (2) Å | µ = 0.22 mm−1 |
b = 8.576 (2) Å | T = 293 K |
c = 20.306 (5) Å | 0.48 × 0.25 × 0.04 mm |
β = 90.742 (4)° |
Bruker SMART CCD area-detector diffractometer | 2831 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2266 reflections with I > 2σ(I) |
Tmin = 0.937, Tmax = 0.998 | Rint = 0.035 |
10964 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.31 e Å−3 |
2831 reflections | Δρmin = −0.27 e Å−3 |
191 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 | ||
N1 | 0.2332 (3) | 0.4280 (3) | 0.75854 (10) | 0.0537 (6) | |
H1A | 0.2921 | 0.3616 | 0.7397 | 0.064* | |
H1B | 0.2625 | 0.4724 | 0.7945 | 0.064* | |
N2 | 0.0765 (2) | 0.3030 (2) | 0.56763 (9) | 0.0431 (5) | |
H2 | 0.0161 | 0.3775 | 0.5558 | 0.052* | |
O1 | 0.2092 (2) | 0.2087 (2) | 0.65522 (8) | 0.0568 (5) | |
O2 | −0.0842 (2) | 0.3124 (2) | 0.46026 (9) | 0.0602 (6) | |
S1 | −0.02268 (8) | 0.59785 (8) | 0.76968 (3) | 0.0466 (2) | |
C2 | 0.0936 (3) | 0.4630 (3) | 0.73142 (10) | 0.0372 (5) | |
C3 | 0.0248 (3) | 0.4060 (2) | 0.67459 (10) | 0.0332 (5) | |
C4 | −0.2396 (3) | 0.4330 (3) | 0.60860 (13) | 0.0457 (6) | |
H4A | −0.2363 | 0.3217 | 0.6001 | 0.055* | |
H4B | −0.2100 | 0.4866 | 0.5687 | 0.055* | |
C5 | −0.4026 (3) | 0.4794 (4) | 0.62600 (17) | 0.0700 (9) | |
H5A | −0.4664 | 0.4747 | 0.5865 | 0.084* | |
H5B | −0.4428 | 0.4045 | 0.6572 | 0.084* | |
C6 | −0.4136 (4) | 0.6365 (4) | 0.65456 (17) | 0.0733 (9) | |
H6A | −0.5201 | 0.6572 | 0.6649 | 0.088* | |
H6B | −0.3827 | 0.7120 | 0.6217 | 0.088* | |
C7 | −0.3169 (3) | 0.6604 (4) | 0.71594 (14) | 0.0561 (7) | |
H7A | −0.2982 | 0.7709 | 0.7224 | 0.067* | |
H7B | −0.3716 | 0.6216 | 0.7539 | 0.067* | |
C8 | −0.1664 (3) | 0.5760 (3) | 0.71018 (11) | 0.0410 (6) | |
C9 | −0.1266 (3) | 0.4723 (2) | 0.66323 (10) | 0.0348 (5) | |
C10 | 0.1099 (3) | 0.2970 (2) | 0.63284 (10) | 0.0358 (5) | |
C11 | 0.1258 (3) | 0.2057 (3) | 0.51622 (11) | 0.0393 (5) | |
C12 | 0.0353 (3) | 0.2094 (3) | 0.45871 (11) | 0.0440 (6) | |
C13 | 0.0714 (4) | 0.1160 (3) | 0.40563 (12) | 0.0556 (7) | |
H13 | 0.0112 | 0.1187 | 0.3675 | 0.067* | |
C14 | 0.1965 (4) | 0.0193 (3) | 0.40959 (14) | 0.0617 (8) | |
H14 | 0.2197 | −0.0452 | 0.3743 | 0.074* | |
C15 | 0.2878 (4) | 0.0167 (3) | 0.46525 (15) | 0.0608 (8) | |
H15 | 0.3732 | −0.0483 | 0.4670 | 0.073* | |
C16 | 0.2536 (3) | 0.1103 (3) | 0.51877 (13) | 0.0499 (6) | |
H16 | 0.3163 | 0.1089 | 0.5562 | 0.060* | |
C17 | −0.2049 (4) | 0.2966 (4) | 0.41266 (14) | 0.0665 (8) | |
H17A | −0.1654 | 0.3157 | 0.3695 | 0.100* | |
H17B | −0.2845 | 0.3705 | 0.4219 | 0.100* | |
H17C | −0.2460 | 0.1928 | 0.4146 | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0486 (14) | 0.0669 (15) | 0.0452 (11) | 0.0091 (11) | −0.0165 (10) | −0.0131 (10) |
N2 | 0.0523 (13) | 0.0423 (12) | 0.0344 (10) | 0.0187 (9) | −0.0073 (9) | −0.0032 (8) |
O1 | 0.0608 (12) | 0.0652 (12) | 0.0439 (9) | 0.0288 (10) | −0.0142 (8) | −0.0020 (8) |
O2 | 0.0615 (13) | 0.0734 (13) | 0.0450 (10) | 0.0203 (10) | −0.0201 (9) | −0.0107 (9) |
S1 | 0.0501 (4) | 0.0524 (4) | 0.0374 (3) | 0.0024 (3) | −0.0013 (3) | −0.0102 (3) |
C2 | 0.0389 (14) | 0.0395 (12) | 0.0331 (11) | −0.0031 (10) | −0.0017 (9) | 0.0011 (9) |
C3 | 0.0340 (13) | 0.0343 (11) | 0.0314 (10) | 0.0010 (9) | −0.0031 (9) | 0.0035 (9) |
C4 | 0.0411 (15) | 0.0415 (13) | 0.0541 (14) | 0.0050 (11) | −0.0126 (11) | −0.0061 (11) |
C5 | 0.0432 (18) | 0.078 (2) | 0.089 (2) | 0.0065 (15) | −0.0170 (15) | −0.0128 (17) |
C6 | 0.0479 (19) | 0.074 (2) | 0.098 (2) | 0.0185 (15) | −0.0123 (17) | −0.0151 (18) |
C7 | 0.0481 (17) | 0.0589 (17) | 0.0614 (16) | 0.0145 (13) | 0.0041 (13) | −0.0069 (13) |
C8 | 0.0386 (14) | 0.0419 (13) | 0.0426 (13) | 0.0022 (10) | 0.0014 (10) | −0.0003 (10) |
C9 | 0.0356 (13) | 0.0325 (11) | 0.0362 (11) | −0.0010 (9) | −0.0016 (9) | 0.0015 (9) |
C10 | 0.0359 (13) | 0.0352 (12) | 0.0363 (11) | 0.0027 (9) | −0.0063 (9) | 0.0014 (9) |
C11 | 0.0460 (15) | 0.0355 (12) | 0.0364 (11) | 0.0016 (10) | 0.0026 (10) | −0.0015 (9) |
C12 | 0.0514 (16) | 0.0437 (14) | 0.0369 (12) | −0.0042 (11) | −0.0008 (11) | −0.0003 (10) |
C13 | 0.070 (2) | 0.0569 (16) | 0.0405 (13) | −0.0074 (15) | 0.0029 (12) | −0.0089 (11) |
C14 | 0.082 (2) | 0.0519 (17) | 0.0519 (15) | −0.0056 (15) | 0.0210 (15) | −0.0133 (13) |
C15 | 0.064 (2) | 0.0492 (16) | 0.0700 (18) | 0.0133 (14) | 0.0207 (15) | −0.0047 (13) |
C16 | 0.0503 (16) | 0.0492 (15) | 0.0503 (14) | 0.0104 (12) | 0.0041 (12) | −0.0007 (11) |
C17 | 0.065 (2) | 0.077 (2) | 0.0566 (16) | −0.0081 (16) | −0.0254 (14) | 0.0132 (15) |
N1—C2 | 1.362 (3) | C6—C7 | 1.509 (4) |
N1—H1A | 0.8600 | C6—H6A | 0.9700 |
N1—H1B | 0.8600 | C6—H6B | 0.9700 |
N2—C10 | 1.353 (3) | C7—C8 | 1.504 (4) |
N2—C11 | 1.408 (3) | C7—H7A | 0.9700 |
N2—H2 | 0.8600 | C7—H7B | 0.9700 |
O1—C10 | 1.232 (3) | C8—C9 | 1.352 (3) |
O2—C12 | 1.366 (3) | C11—C16 | 1.382 (3) |
O2—C17 | 1.425 (3) | C11—C12 | 1.401 (3) |
S1—C2 | 1.728 (2) | C12—C13 | 1.383 (3) |
S1—C8 | 1.738 (2) | C13—C14 | 1.370 (4) |
C2—C3 | 1.383 (3) | C13—H13 | 0.9300 |
C3—C9 | 1.452 (3) | C14—C15 | 1.374 (4) |
C3—C10 | 1.469 (3) | C14—H14 | 0.9300 |
C4—C9 | 1.512 (3) | C15—C16 | 1.386 (4) |
C4—C5 | 1.520 (4) | C15—H15 | 0.9300 |
C4—H4A | 0.9700 | C16—H16 | 0.9300 |
C4—H4B | 0.9700 | C17—H17A | 0.9600 |
C5—C6 | 1.471 (4) | C17—H17B | 0.9600 |
C5—H5A | 0.9700 | C17—H17C | 0.9600 |
C5—H5B | 0.9700 | ||
C2—N1—H1A | 120.0 | C6—C7—H7B | 109.6 |
C2—N1—H1B | 120.0 | H7A—C7—H7B | 108.1 |
H1A—N1—H1B | 120.0 | C9—C8—C7 | 127.1 (2) |
C10—N2—C11 | 129.7 (2) | C9—C8—S1 | 111.86 (18) |
C10—N2—H2 | 115.1 | C7—C8—S1 | 120.99 (18) |
C11—N2—H2 | 115.1 | C8—C9—C3 | 112.7 (2) |
C12—O2—C17 | 118.6 (2) | C8—C9—C4 | 119.6 (2) |
C2—S1—C8 | 92.08 (11) | C3—C9—C4 | 127.6 (2) |
N1—C2—C3 | 129.4 (2) | O1—C10—N2 | 121.7 (2) |
N1—C2—S1 | 119.40 (17) | O1—C10—C3 | 122.4 (2) |
C3—C2—S1 | 111.20 (17) | N2—C10—C3 | 115.89 (19) |
C2—C3—C9 | 112.2 (2) | C16—C11—C12 | 119.3 (2) |
C2—C3—C10 | 119.3 (2) | C16—C11—N2 | 125.2 (2) |
C9—C3—C10 | 128.45 (19) | C12—C11—N2 | 115.5 (2) |
C9—C4—C5 | 111.8 (2) | O2—C12—C13 | 125.0 (2) |
C9—C4—H4A | 109.2 | O2—C12—C11 | 114.6 (2) |
C5—C4—H4A | 109.2 | C13—C12—C11 | 120.4 (2) |
C9—C4—H4B | 109.2 | C14—C13—C12 | 119.6 (3) |
C5—C4—H4B | 109.2 | C14—C13—H13 | 120.2 |
H4A—C4—H4B | 107.9 | C12—C13—H13 | 120.2 |
C6—C5—C4 | 113.4 (3) | C15—C14—C13 | 120.6 (2) |
C6—C5—H5A | 108.9 | C15—C14—H14 | 119.7 |
C4—C5—H5A | 108.9 | C13—C14—H14 | 119.7 |
C6—C5—H5B | 108.9 | C14—C15—C16 | 120.5 (3) |
C4—C5—H5B | 108.9 | C14—C15—H15 | 119.7 |
H5A—C5—H5B | 107.7 | C16—C15—H15 | 119.7 |
C5—C6—C7 | 114.3 (3) | C11—C16—C15 | 119.6 (3) |
C5—C6—H6A | 108.7 | C11—C16—H16 | 120.2 |
C7—C6—H6A | 108.7 | C15—C16—H16 | 120.2 |
C5—C6—H6B | 108.7 | O2—C17—H17A | 109.5 |
C7—C6—H6B | 108.7 | O2—C17—H17B | 109.5 |
H6A—C6—H6B | 107.6 | H17A—C17—H17B | 109.5 |
C8—C7—C6 | 110.4 (2) | O2—C17—H17C | 109.5 |
C8—C7—H7A | 109.6 | H17A—C17—H17C | 109.5 |
C6—C7—H7A | 109.6 | H17B—C17—H17C | 109.5 |
C8—C7—H7B | 109.6 | ||
C8—S1—C2—N1 | −179.4 (2) | C5—C4—C9—C3 | 159.3 (2) |
C8—S1—C2—C3 | 0.96 (18) | C11—N2—C10—O1 | 9.1 (4) |
N1—C2—C3—C9 | 179.3 (2) | C11—N2—C10—C3 | −173.1 (2) |
S1—C2—C3—C9 | −1.1 (2) | C2—C3—C10—O1 | 28.5 (3) |
N1—C2—C3—C10 | −3.4 (4) | C9—C3—C10—O1 | −154.7 (2) |
S1—C2—C3—C10 | 176.22 (16) | C2—C3—C10—N2 | −149.3 (2) |
C9—C4—C5—C6 | 45.6 (4) | C9—C3—C10—N2 | 27.4 (3) |
C4—C5—C6—C7 | −57.6 (4) | C10—N2—C11—C16 | −20.0 (4) |
C5—C6—C7—C8 | 37.7 (4) | C10—N2—C11—C12 | 160.2 (2) |
C6—C7—C8—C9 | −10.1 (4) | C17—O2—C12—C13 | 17.7 (4) |
C6—C7—C8—S1 | 173.4 (2) | C17—O2—C12—C11 | −163.6 (2) |
C2—S1—C8—C9 | −0.60 (19) | C16—C11—C12—O2 | −177.3 (2) |
C2—S1—C8—C7 | 176.4 (2) | N2—C11—C12—O2 | 2.6 (3) |
C7—C8—C9—C3 | −176.7 (2) | C16—C11—C12—C13 | 1.5 (4) |
S1—C8—C9—C3 | 0.1 (3) | N2—C11—C12—C13 | −178.7 (2) |
C7—C8—C9—C4 | 0.9 (4) | O2—C12—C13—C14 | 178.7 (2) |
S1—C8—C9—C4 | 177.63 (17) | C11—C12—C13—C14 | 0.0 (4) |
C2—C3—C9—C8 | 0.6 (3) | C12—C13—C14—C15 | −1.3 (4) |
C10—C3—C9—C8 | −176.3 (2) | C13—C14—C15—C16 | 1.0 (4) |
C2—C3—C9—C4 | −176.7 (2) | C12—C11—C16—C15 | −1.8 (4) |
C10—C3—C9—C4 | 6.4 (4) | N2—C11—C16—C15 | 178.4 (2) |
C5—C4—C9—C8 | −17.9 (3) | C14—C15—C16—C11 | 0.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.86 | 2.27 | 2.823 (3) | 122 |
N1—H1B···O1i | 0.86 | 2.28 | 3.015 (3) | 143 |
N2—H2···O2 | 0.86 | 2.19 | 2.577 (3) | 107 |
C16—H16···O1 | 0.93 | 2.39 | 2.927 (3) | 117 |
Symmetry code: (i) −x+1/2, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C16H18N2O2S |
Mr | 302.38 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 8.709 (2), 8.576 (2), 20.306 (5) |
β (°) | 90.742 (4) |
V (Å3) | 1516.6 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.48 × 0.25 × 0.04 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.937, 0.998 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10964, 2831, 2266 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.147, 1.09 |
No. of reflections | 2831 |
No. of parameters | 191 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.27 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), PARST (Nardelli, 1995); PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.8600 | 2.2700 | 2.823 (3) | 122.00 |
N1—H1B···O1i | 0.8600 | 2.2800 | 3.015 (3) | 143.00 |
N2—H2···O2 | 0.8600 | 2.1900 | 2.577 (3) | 107.00 |
C16—H16···O1 | 0.9300 | 2.3900 | 2.927 (3) | 117.00 |
Symmetry code: (i) −x+1/2, y+1/2, −z+3/2. |
The title compound (I) is one of a series of 3-aryl carboximides. These compounds display different biological activities, such as antitubercular, antibacterial and antifungal activities (Mohan & Saravanan 2003). Schiff bases containing sulfur are the most effective (Csaszar & Morvay 1983; Lakshmi et al., 1985; Cohen et al.,1977).
The molecular structure and the packing diagram of (I) are shown in Figures (1) and (2) respectively. The thiophene ring is essentially planar, with a short C8—C9 bond distance [1.352 (3) Å,], indicating the absence of delocalization in the double bonds. This is also reflected in the S1—C2 and S1—C8 distances, which are shorter than the normal C—S distances. The cyclohexene ring adopts a half-chair conformation, with the puckering parameters q2 = 0.325 (2) Å, Φ = -99.4 (3)° and θ = 130.7 (2)°. (Cremer & Pople, 1975; Spek, 2003). The thiophene ring makes a dihedral angle of 12.9 (1) ° with the o-methoxyphenyl ring.
The molecular structure of (I) is stabilized by intramolecular C—H···O and N—H···O hydrogen bonds and by intermolecular N—H···O interactions. (Table 2) The intramolecular C16—H16···O1 and N1—H1···O1 hydrogen bonds form pseudo-six membered rings and N2—H2···O2 forms a pseudo five membered ring, thus locking the molecular conformation and eliminating flexibility. Molecules are linked via N—H···O interactions, forming zigzag chains along the c axis, (Fig. 2).