In the title compound, the central pyrazole ring adopts a twisted conformation on the –CH—CH2– bond and its mean plane makes dihedral angles of 7.19 (12) and 71.13 (11)° with the attached thiophene and toluene rings, respectively. In the crystal, molecules are linked by N—H⋯S hydrogen bonds, forming chains propagating along [010].
Keywords: crystal structure, pyrazole, thiophene, carbothioamide, C—H⋯S hydrogen bonds, N—H⋯π interactions, π–π interactions
Abstract
In the title compound, C15H15N3S2, the central pyrazole ring adopts a twisted conformation on the –CH—CH2– bond. Its mean plane makes dihedral angles of 7.19 (12) and 71.13 (11)° with those of the thiophene and toluene rings, respectively. The carbothiamide group [C(=S)—N] is inclined to the pyrazole ring mean plane by 16.8 (2)°. In the crystal, molecules are linked by N—H⋯S hydrogen bonds, forming chains propagating along [010]. Within the chains, there are N—H⋯π interactions present. Between the chains there are weak parallel slipped π–π interactions involving inversion-related thiophene and pyrazole rings [inter-centroid distance = 3.7516 (14) Å; inter-planar distance = 3.5987 (10) Å; slippage = 1.06 Å].
Chemical context
Five-membered heterocyclic pyrazole analogues have been used extensively as building blocks in organic synthesis. They have been transformed efficiently into molecules of potential medicinal and pharmaceutical important. Pyrazole derivatives have known to exhibit diverse biological applications such as antidiabetic,anaesthetic, antimicrobial and antioxidant. In addition, they have also shown potential anticancer and antiamoebic activity and to be potent and selective inhibitors of tissue-nonspecific alkaline phosphatase (Sidique et al. 2009 ▸). Earlier we synthesized α and β-unsaturated compounds which served as useful intermediates for the synthesis of pyrazolines (Manjula et al., 2013 ▸) and thiazepines (Manjunath et al., 2014 ▸). As part of our ongoing research on pyrazole analogues, the title compound was synthesized and we report herein on its crystal structure. Studies of the biological activity of the title compound are underway and will be reported elsewhere.
Structural commentary
The molecular structure of the title compound is illustrated in Fig. 1 ▸. The central pyrazole ring (N7/N8/C8–C10) adopts a twisted conformation with respect to the C9—C10 bond and its mean plane makes dihedral angles of 7.19 (12) and 71.13 (11)° with the thiophene (S1/C2–C5) and toluene (C14–C19) rings, respectively. The carbothiamide group [C11(=S13)N12] lies in the plane of the pyrazole ring, as indicated by the torsion angles N12—C11—N8—N7 = 0.6 (3) and S13—C11—N8—N7 = 179.96 (16)°, and adopts +syn-periplanar and +anti-periplanar conformations, respectively. The title compound possess a chiral center at atom C9 but crystallized as a racemate.
Figure 1.
View of the molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
Supramolecular features
In the crystal, molecules are linked by N—H⋯S hydrogen bonds, forming chains propagating along [010]. Within the chains there are N—H⋯π interactions involving the toluene ring (Fig. 2 ▸ and Table 1 ▸). Between the chains there are weak parallel slipped π–π interactions involving inversion-related thiophene and pyrazole rings [Cg1⋯Cg2i = 3.7516 (14) Å; inter-planar distance = 3.5987 (10) Å; slippage = 1.06 Å; Cg1 and Cg2 are the centroids of rings S1/C2–C5 and N7/N8/C8–C10, respectively; symmetry code: (i) −x + 2, −y + 1, −z + 1].
Figure 2.
A view along the a axis of the crystal packing of the title compound. The hydrogen bonds and C—H⋯π interactions are shown as dashed lines (see Table 1 ▸ for details). C-bound H atoms have been omitted for clarity.
Table 1. Hydrogen-bond geometry (, ).
Cg3 is the centroid of the benzene ring C14C19.
| DHA | DH | HA | D A | DHA |
|---|---|---|---|---|
| N12H12AS13i | 0.86 | 2.83 | 3.620(2) | 154 |
| N12H12B Cg3i | 0.86 | 2.81 | 3.443(2) | 132 |
Symmetry code: (i) 
.
Database survey
A search of the Cambridge Structural Database (Version 5.36, May 2015; Groom & Allen, 2014 ▸) revealed seven structures containing the 3-(thiophen-2-yl)-pyrazole unit. Amongst these are two thioamides; the phenyl derivative of the title compound, 5-phenyl-3-(2-thienyl)-2-pyrazoline-1-thioamide (HEFXEW; Işık et al., 2006 ▸), and 1-(N-ethylthiocarbamoyl)-3,5-bis(2-thienyl)-2-pyrazoline (YINFUX; Köysal et al., 2007 ▸). In these two compounds, the pyrazole rings have envelope conformations with the methine C atom as the flap, and the mean planes of the two rings are inclined to one another by 11.98 and 10.13°, respectively. This is in contrast to the situation in the title compound where the pyrazole ring has a twisted conformation on the –CH–CH2– bond and its mean plane is inclined to the thiophene ring by 7.19 (12)°. In the crystal of the phenyl derivative (HEFXEW), molecules are also linked by N—H⋯S hydrogen bonds, forming chains.
Synthesis and crystallization
A mixture of 3-(4-methylphenyl)-1-(thiophen-2-yl)prop-2-en-1-one (0.001 mol) and thiosemicarbazine hydrochloride (0.01 mol) and potassium hydroxide (0.02 mol) in ethyl alcohol (20 ml) was refluxed on a water bath for 6–8 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was poured into ice-cold water and stirred. The solid that separated was filtered, and washed with ice-cold water. The product was recrystallized from ethyl alcohol to give the title compound as rectangular yellow crystals. Analysis calculated for C15H15N3S2: C, 59.77; H, 5.02; N, 13.94%; found: C, 59.74; H, 5.06; N, 13.88%. 1H NMR (CDCl3): δ 2.297 (s, 3H, CH3), (dd, 1H, C4—Hb: J = 18.0, 8.5 Hz), (dd, 1H, C4—Hb: J 18.0, 8.5 Hz), 5.976–6.013 (dd, 1H, C—Ha: J = 18.0, 12.0 Hz), 6.163–7.169 (m, 7H, Ar—H and thiophene ring-H), 7.330 (s, 2H, –NH2). 13C NMR (CDCl3): δ 43.77, 1 C, C-4), 63.34 (1 C, C-5), 125.35 (2C, Ar—C), 127.88 (1C, 5 m ring-C), 129.57 (1C, Ar—C), 129.67 (1C, Ar—C), 129.72 (1C, 5 m ring-C), 130.01 (1C, 5 m ring-C), 134.12, (1C, 5 m ring-C), 137.31 (1C, Ar—C), 138.67 (1C, Ar—C), 151.38 (1C, C-3), 176.36 (1C, C=S). MS (m/z): 303 (M+2, 10) 302 (M+1, 18), 301 (M+, 100), 284 (40), 161 (15).
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. H atoms were fixed geometrically and allowed to ride on their parent atoms: C—H = 0.93–0.98 Å with U iso(H) = 1.5U eq(C) for methyl H atoms and 1.2U eq(C) for other H atoms.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C15H15N3S2 |
| M r | 301.44 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 296 |
| a, b, c () | 8.1035(4), 12.0193(5), 15.1312(7) |
| () | 94.347(2) |
| V (3) | 1469.52(12) |
| Z | 4 |
| Radiation type | Cu K |
| (mm1) | 3.22 |
| Crystal size (mm) | 0.27 0.25 0.24 |
| Data collection | |
| Diffractometer | Bruker X8 Proteum |
| Absorption correction | Multi-scan (SADABS; Bruker, 2013 ▸) |
| T min, T max | 0.477, 0.512 |
| No. of measured, independent and observed [I > 2(I)] reflections | 11926, 2397, 2262 |
| R int | 0.044 |
| (sin /)max (1) | 0.583 |
| Refinement | |
| R[F 2 > 2(F 2)], wR(F 2), S | 0.046, 0.127, 1.07 |
| No. of reflections | 2397 |
| No. of parameters | 183 |
| H-atom treatment | H-atom parameters constrained |
| max, min (e 3) | 0.37, 0.44 |
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015010774/su5147sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015010774/su5147Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015010774/su5147Isup3.cml
CCDC reference: 1404788
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors are thankful to the IOE, Vijnana Bhavana, University of Mysore, Mysore, for providing the single-crystal X-ray diffraction facility. IW is grateful to An-Najah National University and Zamala (fellowship program for the development of university education) for financial support.
supplementary crystallographic information
Crystal data
| C15H15N3S2 | F(000) = 632 |
| Mr = 301.44 | Dx = 1.362 Mg m−3 |
| Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
| Hall symbol: -P 2ybc | Cell parameters from 2262 reflections |
| a = 8.1035 (4) Å | θ = 5.5–64.1° |
| b = 12.0193 (5) Å | µ = 3.22 mm−1 |
| c = 15.1312 (7) Å | T = 296 K |
| β = 94.347 (2)° | Rectangle, yellow |
| V = 1469.52 (12) Å3 | 0.27 × 0.25 × 0.24 mm |
| Z = 4 |
Data collection
| Bruker X8 Proteum diffractometer | 2397 independent reflections |
| Radiation source: Bruker MicroStar microfocus rotating anode | 2262 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.044 |
| Detector resolution: 18.4 pixels mm-1 | θmax = 64.1°, θmin = 5.5° |
| φ and ω scans | h = −9→9 |
| Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −13→13 |
| Tmin = 0.477, Tmax = 0.512 | l = −16→17 |
| 11926 measured reflections |
Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
| wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.074P)2 + 0.626P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max < 0.001 |
| 2397 reflections | Δρmax = 0.37 e Å−3 |
| 183 parameters | Δρmin = −0.44 e Å−3 |
| 0 restraints | Extinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0160 (12) |
Special details
| 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.83886 (8) | 0.35843 (5) | 0.55113 (4) | 0.0527 (2) | |
| S13 | 0.41488 (9) | 0.76951 (5) | 0.77019 (4) | 0.0611 (3) | |
| N7 | 0.6560 (2) | 0.55350 (14) | 0.63166 (11) | 0.0396 (5) | |
| N8 | 0.5837 (2) | 0.65224 (14) | 0.65865 (11) | 0.0418 (6) | |
| N12 | 0.5024 (3) | 0.55813 (17) | 0.77851 (13) | 0.0572 (7) | |
| C2 | 0.9012 (3) | 0.3098 (2) | 0.45389 (18) | 0.0561 (8) | |
| C3 | 0.8661 (3) | 0.3801 (2) | 0.38623 (17) | 0.0613 (9) | |
| C4 | 0.7858 (3) | 0.4794 (2) | 0.41081 (15) | 0.0494 (8) | |
| C5 | 0.7627 (3) | 0.47817 (18) | 0.50124 (13) | 0.0400 (6) | |
| C6 | 0.6841 (2) | 0.56438 (17) | 0.54966 (13) | 0.0368 (6) | |
| C9 | 0.5786 (3) | 0.73914 (17) | 0.58990 (13) | 0.0381 (6) | |
| C10 | 0.6257 (3) | 0.67214 (18) | 0.50885 (13) | 0.0417 (6) | |
| C11 | 0.5039 (3) | 0.65429 (18) | 0.73411 (14) | 0.0438 (7) | |
| C14 | 0.6974 (2) | 0.83434 (15) | 0.61077 (13) | 0.0326 (5) | |
| C15 | 0.8130 (3) | 0.83437 (18) | 0.68204 (14) | 0.0421 (7) | |
| C16 | 0.9258 (3) | 0.92083 (19) | 0.69439 (15) | 0.0469 (7) | |
| C17 | 0.9243 (3) | 1.00979 (18) | 0.63663 (14) | 0.0437 (7) | |
| C18 | 0.8065 (3) | 1.00989 (18) | 0.56564 (15) | 0.0470 (7) | |
| C19 | 0.6951 (3) | 0.92360 (18) | 0.55243 (14) | 0.0419 (6) | |
| C20 | 1.0453 (4) | 1.1050 (2) | 0.65103 (19) | 0.0688 (10) | |
| H2 | 0.95400 | 0.24170 | 0.44810 | 0.0670* | |
| H3 | 0.89180 | 0.36530 | 0.32850 | 0.0740* | |
| H4 | 0.75340 | 0.53690 | 0.37220 | 0.0590* | |
| H9 | 0.46560 | 0.76780 | 0.57940 | 0.0460* | |
| H10A | 0.53080 | 0.66110 | 0.46670 | 0.0500* | |
| H10B | 0.71300 | 0.70870 | 0.47930 | 0.0500* | |
| H12A | 0.55020 | 0.50040 | 0.75860 | 0.0690* | |
| H12B | 0.45370 | 0.55400 | 0.82700 | 0.0690* | |
| H15 | 0.81560 | 0.77590 | 0.72240 | 0.0500* | |
| H16 | 1.00410 | 0.91880 | 0.74260 | 0.0560* | |
| H18 | 0.80230 | 1.06920 | 0.52610 | 0.0560* | |
| H19 | 0.61750 | 0.92520 | 0.50390 | 0.0500* | |
| H20A | 0.98990 | 1.16790 | 0.67420 | 0.1030* | |
| H20B | 1.08790 | 1.12470 | 0.59560 | 0.1030* | |
| H20C | 1.13490 | 1.08270 | 0.69240 | 0.1030* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0578 (4) | 0.0494 (4) | 0.0530 (4) | −0.0001 (3) | 0.0172 (3) | −0.0061 (2) |
| S13 | 0.0750 (5) | 0.0495 (4) | 0.0628 (4) | −0.0051 (3) | 0.0306 (3) | −0.0180 (3) |
| N7 | 0.0483 (10) | 0.0317 (9) | 0.0408 (9) | −0.0044 (7) | 0.0164 (7) | −0.0045 (7) |
| N8 | 0.0561 (11) | 0.0321 (9) | 0.0395 (9) | −0.0044 (8) | 0.0188 (8) | −0.0026 (7) |
| N12 | 0.0786 (14) | 0.0492 (12) | 0.0478 (11) | −0.0064 (10) | 0.0304 (10) | 0.0030 (9) |
| C2 | 0.0557 (14) | 0.0474 (14) | 0.0681 (16) | −0.0092 (11) | 0.0240 (12) | −0.0190 (12) |
| C3 | 0.0728 (17) | 0.0637 (16) | 0.0506 (14) | −0.0182 (13) | 0.0258 (12) | −0.0257 (13) |
| C4 | 0.0583 (14) | 0.0489 (13) | 0.0429 (12) | −0.0148 (11) | 0.0156 (10) | −0.0163 (10) |
| C5 | 0.0403 (11) | 0.0424 (12) | 0.0386 (10) | −0.0145 (9) | 0.0112 (8) | −0.0087 (9) |
| C6 | 0.0377 (10) | 0.0362 (11) | 0.0372 (10) | −0.0118 (8) | 0.0084 (8) | −0.0055 (8) |
| C9 | 0.0409 (11) | 0.0348 (11) | 0.0391 (11) | −0.0036 (8) | 0.0070 (8) | −0.0004 (8) |
| C10 | 0.0509 (12) | 0.0387 (11) | 0.0357 (10) | −0.0121 (9) | 0.0050 (9) | −0.0036 (9) |
| C11 | 0.0491 (12) | 0.0444 (12) | 0.0398 (11) | −0.0122 (10) | 0.0157 (9) | −0.0080 (9) |
| C14 | 0.0362 (10) | 0.0275 (9) | 0.0349 (9) | 0.0015 (8) | 0.0087 (8) | −0.0029 (7) |
| C15 | 0.0504 (12) | 0.0342 (11) | 0.0410 (11) | 0.0016 (9) | −0.0004 (9) | 0.0053 (8) |
| C16 | 0.0491 (12) | 0.0474 (13) | 0.0430 (11) | −0.0019 (10) | −0.0040 (9) | −0.0065 (10) |
| C17 | 0.0495 (12) | 0.0371 (12) | 0.0459 (11) | −0.0077 (9) | 0.0137 (9) | −0.0128 (9) |
| C18 | 0.0642 (14) | 0.0324 (11) | 0.0451 (11) | −0.0070 (10) | 0.0090 (10) | 0.0057 (9) |
| C19 | 0.0508 (12) | 0.0375 (11) | 0.0366 (10) | −0.0002 (9) | −0.0010 (9) | 0.0022 (8) |
| C20 | 0.0790 (19) | 0.0592 (17) | 0.0697 (17) | −0.0309 (15) | 0.0151 (14) | −0.0182 (14) |
Geometric parameters (Å, º)
| S1—C2 | 1.695 (3) | C15—C16 | 1.387 (3) |
| S1—C5 | 1.718 (2) | C16—C17 | 1.381 (3) |
| S13—C11 | 1.672 (2) | C17—C18 | 1.382 (3) |
| N7—N8 | 1.398 (2) | C17—C20 | 1.512 (4) |
| N7—C6 | 1.285 (3) | C18—C19 | 1.380 (3) |
| N8—C9 | 1.473 (3) | C2—H2 | 0.9300 |
| N8—C11 | 1.354 (3) | C3—H3 | 0.9300 |
| N12—C11 | 1.337 (3) | C4—H4 | 0.9300 |
| N12—H12B | 0.8600 | C9—H9 | 0.9800 |
| N12—H12A | 0.8600 | C10—H10A | 0.9700 |
| C2—C3 | 1.341 (4) | C10—H10B | 0.9700 |
| C3—C4 | 1.422 (3) | C15—H15 | 0.9300 |
| C4—C5 | 1.395 (3) | C16—H16 | 0.9300 |
| C5—C6 | 1.445 (3) | C18—H18 | 0.9300 |
| C6—C10 | 1.496 (3) | C19—H19 | 0.9300 |
| C9—C14 | 1.513 (3) | C20—H20A | 0.9600 |
| C9—C10 | 1.539 (3) | C20—H20B | 0.9600 |
| C14—C19 | 1.389 (3) | C20—H20C | 0.9600 |
| C14—C15 | 1.374 (3) | ||
| C2—S1—C5 | 91.62 (11) | C18—C17—C20 | 120.9 (2) |
| N8—N7—C6 | 107.73 (16) | C17—C18—C19 | 121.2 (2) |
| N7—N8—C9 | 112.69 (15) | C14—C19—C18 | 120.8 (2) |
| N7—N8—C11 | 119.94 (17) | S1—C2—H2 | 124.00 |
| C9—N8—C11 | 126.37 (17) | C3—C2—H2 | 124.00 |
| H12A—N12—H12B | 120.00 | C2—C3—H3 | 123.00 |
| C11—N12—H12A | 120.00 | C4—C3—H3 | 123.00 |
| C11—N12—H12B | 120.00 | C3—C4—H4 | 125.00 |
| S1—C2—C3 | 112.67 (19) | C5—C4—H4 | 125.00 |
| C2—C3—C4 | 113.8 (2) | N8—C9—H9 | 110.00 |
| C3—C4—C5 | 110.2 (2) | C10—C9—H9 | 110.00 |
| S1—C5—C4 | 111.68 (17) | C14—C9—H9 | 110.00 |
| S1—C5—C6 | 122.38 (15) | C6—C10—H10A | 111.00 |
| C4—C5—C6 | 125.9 (2) | C6—C10—H10B | 111.00 |
| N7—C6—C10 | 114.39 (17) | C9—C10—H10A | 111.00 |
| N7—C6—C5 | 122.27 (18) | C9—C10—H10B | 111.00 |
| C5—C6—C10 | 123.33 (17) | H10A—C10—H10B | 109.00 |
| N8—C9—C10 | 101.33 (16) | C14—C15—H15 | 120.00 |
| N8—C9—C14 | 113.93 (17) | C16—C15—H15 | 120.00 |
| C10—C9—C14 | 111.69 (18) | C15—C16—H16 | 119.00 |
| C6—C10—C9 | 102.35 (16) | C17—C16—H16 | 119.00 |
| N8—C11—N12 | 115.5 (2) | C17—C18—H18 | 119.00 |
| S13—C11—N12 | 122.08 (18) | C19—C18—H18 | 119.00 |
| S13—C11—N8 | 122.39 (16) | C14—C19—H19 | 120.00 |
| C9—C14—C15 | 123.31 (18) | C18—C19—H19 | 120.00 |
| C9—C14—C19 | 118.29 (18) | C17—C20—H20A | 109.00 |
| C15—C14—C19 | 118.32 (18) | C17—C20—H20B | 109.00 |
| C14—C15—C16 | 120.6 (2) | C17—C20—H20C | 109.00 |
| C15—C16—C17 | 121.4 (2) | H20A—C20—H20B | 110.00 |
| C16—C17—C20 | 121.4 (2) | H20A—C20—H20C | 109.00 |
| C16—C17—C18 | 117.7 (2) | H20B—C20—H20C | 110.00 |
| C5—S1—C2—C3 | −0.2 (2) | C4—C5—C6—N7 | 174.6 (2) |
| C2—S1—C5—C4 | 0.1 (2) | C4—C5—C6—C10 | −4.2 (3) |
| C2—S1—C5—C6 | 179.6 (2) | C5—C6—C10—C9 | −171.56 (19) |
| C6—N7—N8—C9 | −5.9 (2) | N7—C6—C10—C9 | 9.6 (2) |
| C6—N7—N8—C11 | 163.41 (18) | C10—C9—C14—C15 | −107.0 (2) |
| N8—N7—C6—C5 | 178.34 (17) | C10—C9—C14—C19 | 69.6 (2) |
| N8—N7—C6—C10 | −2.8 (2) | N8—C9—C14—C19 | −176.34 (18) |
| C11—N8—C9—C14 | 82.7 (3) | N8—C9—C10—C6 | −11.5 (2) |
| C9—N8—C11—N12 | 168.3 (2) | C14—C9—C10—C6 | 110.18 (18) |
| N7—N8—C11—S13 | 179.96 (16) | N8—C9—C14—C15 | 7.1 (3) |
| N7—N8—C9—C10 | 11.3 (2) | C9—C14—C15—C16 | 175.7 (2) |
| C11—N8—C9—C10 | −157.2 (2) | C19—C14—C15—C16 | −0.9 (3) |
| N7—N8—C11—N12 | 0.6 (3) | C9—C14—C19—C18 | −176.6 (2) |
| N7—N8—C9—C14 | −108.84 (18) | C15—C14—C19—C18 | 0.2 (3) |
| C9—N8—C11—S13 | −12.4 (3) | C14—C15—C16—C17 | 0.9 (4) |
| S1—C2—C3—C4 | 0.3 (3) | C15—C16—C17—C18 | −0.1 (4) |
| C2—C3—C4—C5 | −0.3 (3) | C15—C16—C17—C20 | 178.9 (2) |
| C3—C4—C5—S1 | 0.1 (3) | C16—C17—C18—C19 | −0.6 (3) |
| C3—C4—C5—C6 | −179.4 (2) | C20—C17—C18—C19 | −179.6 (2) |
| S1—C5—C6—N7 | −4.9 (3) | C17—C18—C19—C14 | 0.6 (3) |
| S1—C5—C6—C10 | 176.33 (17) |
Hydrogen-bond geometry (Å, º)
Cg3 is the centroid of the benzene ring C14–C19.
| D—H···A | D—H | H···A | D···A | D—H···A |
| N12—H12A···S13i | 0.86 | 2.83 | 3.620 (2) | 154 |
| N12—H12B···Cg3i | 0.86 | 2.81 | 3.443 (2) | 132 |
Symmetry code: (i) −x+1, y−1/2, −z+3/2.
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015010774/su5147sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015010774/su5147Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015010774/su5147Isup3.cml
CCDC reference: 1404788
Additional supporting information: crystallographic information; 3D view; checkCIF report