The title heterocyclic compound is contains an oxadizole and two chloro-substituted phenyl rings. In the crystal, C—H⋯N hydrogen bonding links the molecules into undulating ribbons parallel to the b axis. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are the H⋯C (18%), H⋯H (17%), H⋯Cl (16.6%), H⋯O (10.4%), H⋯N (8.9%) and H⋯S (5.9%) interactions.
Keywords: oxadizole, chlorophenyl, X-ray structure, Hirshfeld surface analysis, crystal structure
Abstract
In the title compound, C16H10Cl2N2O2S, the dihedral angles formed by the chloro-substituted benzene rings with the central oxadiazole ring are 6.54 (9) and 6.94 (8)°. In the crystal, C—H⋯N hydrogen bonding links the molecules into undulating ribbons running parallel to the b axis. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are the H⋯C (18%), H⋯H (17%), H⋯Cl (16.6%), H⋯O (10.4%), H⋯N (8.9%) and H⋯S (5.9%) interactions.
Chemical context
Heterocyclic compounds are well known for their applications in agriculture (Jakobi et al., 1999 ▸) and for the synthesis of pharmaceuticals (Vitaku et al., 2014 ▸). The broad range of biological activities of heterocyclic compounds has always fascinated chemists and the literature reveals many approaches to synthesize and derivatize libraries of heterocyclic compounds (Khan et al., 2011 ▸; Chohan et al., 2006 ▸; Khan et al., 2005 ▸). The wide range of applications and biological activities of this class of compounds is due to the presence of heteroatoms (N, O, S) in the molecule (Kashtoh et al., 2014 ▸). Oxadiazoles are among the most widely studied moieties of organic chemistry due to their many important chemical and biological properties including antimycobacterial (Jha et al., 2009 ▸), antioxidant (Fadda et al., 2011 ▸), anticancer (Zhang et al., 2011 ▸), antitumor (Loetchutinat et al., 2003 ▸), antimicrobial (Şahin et al., 2002 ▸), antifungal (Zou et al., 2002 ▸), anti-inflammatory (Palaska et al., 2002 ▸) and hypotensive (Tyagi & Kumar, 2002 ▸) activities.
Structural commentary
The title compound (Fig. 1 ▸) is an oxadiazole derivative containing two chlorophenyl substituents attached to a central oxadiazole thioethanone unit. The C1–C6 and C11–C16 phenyl rings form dihedral angles of 6.54 (9) and 6.94 (8)°, respectively, with the oxadiazole ring. The dihedral angle between the oxadiazole ring and the mean plane through the S1/O1/C7–C8 fragment is 10.75 (8)°. Bond lengths and angles are not unusual.
Figure 1.
The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level.
Supramolecular features
In the crystal, molecules are connected by C—H⋯N hydrogen interactions, forming undulating ribbons parallel to the b axis (Table 1 ▸, Fig. 2 ▸). The importance of these interactions in stabilizing the crystal structure may be determined by comparison with those found in similar related compounds. For instance, in the crystal structure of 2-{5-[(1H-1,2,4-triazol-1-yl)methyl]-1,3,4-oxadiazol-2-ylthio}-1-(2,4-dichlorophenyl)ethanone (Xu et al., 2005 ▸) molecules are linked into chains via C—H⋯N hydrogen bonds having H⋯N separations of 2.48 Å. and C—H⋯C interactions having H⋯N distances of 2.41 Å. Similarly, in the crystal structure of 1,3-bis{[5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}propan-2-one (Xia et al., 2011 ▸), two oxadiazole rings are present and form intermolecular hydrogen bonds of the type C—H⋯N with distances of 2.51 and 2.54 Å, respectively. Moreover, in the structure of the latter compound, further stabilization of the crystal structure is provided by π–π interactions involving the pyridyl and oxadiazole rings with centroid-to-centroid distances of 3.883 Å.
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C1—H1B⋯N1i | 0.93 | 2.48 | 3.353 (3) | 157 |
Symmetry code: (i) 
.
Figure 2.
Partial crystal packing of the title compound showing the formation of a undulating ribbon parallel to the b axis through C—H⋯N hydrogen bonds (dashed lines).
Hirshfeld surface analysis
The Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ▸) of the crystal structure suggests that the contribution to the crystal packing of the H⋯N interaction is 8.9% (Fig. 3 ▸). Other important interactions based upon the percentages are H⋯H (17%), H⋯O (10.4%), H⋯C (18%), H⋯S (5.9%) and H⋯Cl (16.6%). These interactions, however, were not found to be involved in hydrogen bonding, as observed for the H⋯N contribution (Fig. 4 ▸). The Hirshfeld surface diagram shows the location of atoms with the potential to form hydrogen bonds. These interactions are represented in two-dimensional fingerprint plots (Fig. 4 ▸), in which the cyan dots indicate the percentage of the interaction over the total Hirshfeld surface.
Figure 3.
d norm mapped on the Hirshfeld surface, visualizing the intermolecular contacts of the title compound. Dotted lines indicate hydrogen bonds.
Figure 4.
Hirshfeld surface two-dimensional fingerprint plot for the title compound (a) showing the: (b) H⋯C, (c) H⋯H, (d) H⋯Cl, (e) H⋯S, (f) H⋯N and (g) H⋯O interactions. The outline of the full fingerprint plots is shown in gray. d i (x axis) and d e (y axis) are the closest internal and external distance (values in Å) from a given point on the Hirshfeld surface contacts.
Synthesis and crystallization
The title compound was synthesized by the procdure reported by Kashtoh et al. (2014 ▸). 4-Chloro-1,3,4-oxadiazole-2-thiol (212 mg,1 mmol) and triethyl amine (0.1 mL) were taken in ethanol (10 mL) and stirred for 10 min. 2-Bromo-4′-chloroacetophenone (232 mg, 1 mmol) was then added slowly into the mixture and refluxed, while progress of the reaction was monitored by TLC. After completion of the reaction, the precipitate was filtered and washed with ethanol. The precipitate was crystallized from methanol to give the title compound in 344 mg, 94% yield.
Refinement
Crystal data, data collection and structure refinement details are summarized in (Table 2 ▸). H atoms were located in a difference-Fourier map, but were positioned with idealized geometry and refined with C—H = 0.93–0.97 Å, and with U iso(H) = 1.2U eq(C).
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C16H10Cl2N2O2S |
| M r | 365.22 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 273 |
| a, b, c (Å) | 19.1513 (7), 11.1589 (4), 7.5071 (3) |
| β (°) | 92.088 (1) |
| V (Å3) | 1603.26 (10) |
| Z | 4 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.55 |
| Crystal size (mm) | 0.47 × 0.39 × 0.11 |
| Data collection | |
| Diffractometer | Bruker SMART APEX CCD area-detector |
| Absorption correction | Multi-scan (SADABS; Bruker, 2000 ▸) |
| T min, T max | 0.784, 0.945 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 11526, 3762, 3058 |
| R int | 0.022 |
| (sin θ/λ)max (Å−1) | 0.667 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.045, 0.132, 1.12 |
| No. of reflections | 3762 |
| No. of parameters | 208 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.34, −0.26 |
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989017003978/rz5206sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017003978/rz5206Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989017003978/rz5206Isup3.cml
CCDC reference: 1537363
Additional supporting information: crystallographic information; 3D view; checkCIF report
supplementary crystallographic information
Crystal data
| C16H10Cl2N2O2S | F(000) = 744 |
| Mr = 365.22 | Dx = 1.513 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 19.1513 (7) Å | Cell parameters from 3559 reflections |
| b = 11.1589 (4) Å | θ = 3.2–27.7° |
| c = 7.5071 (3) Å | µ = 0.55 mm−1 |
| β = 92.088 (1)° | T = 273 K |
| V = 1603.26 (10) Å3 | Block, colorless |
| Z = 4 | 0.47 × 0.39 × 0.11 mm |
Data collection
| Bruker SMART APEX CCD area-detector diffractometer | 3762 independent reflections |
| Radiation source: fine-focus sealed tube | 3058 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.022 |
| ω scan | θmax = 28.3°, θmin = 1.1° |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −25→25 |
| Tmin = 0.784, Tmax = 0.945 | k = −13→14 |
| 11526 measured reflections | l = −9→9 |
Refinement
| 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) = 0.132 | H-atom parameters constrained |
| S = 1.12 | w = 1/[σ2(Fo2) + (0.069P)2 + 0.2639P] where P = (Fo2 + 2Fc2)/3 |
| 3762 reflections | (Δ/σ)max < 0.001 |
| 208 parameters | Δρmax = 0.34 e Å−3 |
| 0 restraints | Δρmin = −0.26 e Å−3 |
Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Cl1 | −0.31166 (3) | 0.71345 (7) | 0.43607 (10) | 0.0711 (2) | |
| Cl2 | 0.54160 (4) | 0.62796 (12) | −0.30547 (16) | 0.1258 (4) | |
| S1 | 0.09911 (2) | 0.52100 (4) | 0.14177 (7) | 0.04411 (16) | |
| O1 | −0.01151 (8) | 0.43467 (13) | 0.3026 (2) | 0.0556 (4) | |
| O2 | 0.21861 (7) | 0.57741 (12) | 0.00900 (19) | 0.0427 (3) | |
| N1 | 0.14210 (9) | 0.72473 (14) | −0.0287 (2) | 0.0457 (4) | |
| N2 | 0.20649 (9) | 0.75906 (16) | −0.1028 (3) | 0.0508 (4) | |
| C1 | −0.14356 (11) | 0.50990 (18) | 0.3877 (3) | 0.0448 (5) | |
| H1B | −0.1303 | 0.4313 | 0.4130 | 0.054* | |
| C2 | −0.20957 (11) | 0.54753 (19) | 0.4258 (3) | 0.0494 (5) | |
| H2B | −0.2410 | 0.4953 | 0.4766 | 0.059* | |
| C3 | −0.22851 (10) | 0.6646 (2) | 0.3873 (3) | 0.0463 (5) | |
| C4 | −0.18228 (10) | 0.74359 (19) | 0.3131 (3) | 0.0471 (5) | |
| H4A | −0.1958 | 0.8222 | 0.2889 | 0.057* | |
| C5 | −0.11620 (10) | 0.70548 (17) | 0.2752 (3) | 0.0428 (4) | |
| H5A | −0.0849 | 0.7583 | 0.2250 | 0.051* | |
| C6 | −0.09600 (9) | 0.58753 (16) | 0.3118 (3) | 0.0375 (4) | |
| C7 | −0.02636 (10) | 0.53891 (16) | 0.2705 (3) | 0.0394 (4) | |
| C8 | 0.02691 (9) | 0.61879 (16) | 0.1858 (3) | 0.0410 (4) | |
| H8A | 0.0415 | 0.6828 | 0.2663 | 0.049* | |
| H8B | 0.0079 | 0.6537 | 0.0761 | 0.049* | |
| C9 | 0.15279 (9) | 0.61954 (16) | 0.0337 (3) | 0.0385 (4) | |
| C10 | 0.24856 (10) | 0.67088 (18) | −0.0775 (3) | 0.0419 (4) | |
| C11 | 0.32086 (10) | 0.6589 (2) | −0.1300 (3) | 0.0466 (5) | |
| C12 | 0.35671 (13) | 0.7597 (2) | −0.1857 (3) | 0.0611 (6) | |
| H12A | 0.3347 | 0.8340 | −0.1876 | 0.073* | |
| C13 | 0.42443 (14) | 0.7499 (3) | −0.2380 (4) | 0.0743 (8) | |
| H13A | 0.4485 | 0.8174 | −0.2747 | 0.089* | |
| C14 | 0.45624 (12) | 0.6400 (3) | −0.2356 (4) | 0.0760 (8) | |
| C15 | 0.42210 (13) | 0.5394 (3) | −0.1805 (5) | 0.0819 (9) | |
| H15A | 0.4444 | 0.4654 | −0.1793 | 0.098* | |
| C16 | 0.35398 (12) | 0.5494 (2) | −0.1265 (4) | 0.0643 (7) | |
| H16A | 0.3305 | 0.4818 | −0.0877 | 0.077* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0415 (3) | 0.0839 (5) | 0.0889 (5) | 0.0064 (3) | 0.0182 (3) | −0.0073 (3) |
| Cl2 | 0.0440 (4) | 0.1827 (11) | 0.1531 (10) | −0.0066 (5) | 0.0351 (5) | 0.0047 (8) |
| S1 | 0.0393 (3) | 0.0369 (3) | 0.0567 (4) | 0.00321 (18) | 0.0088 (2) | 0.0004 (2) |
| O1 | 0.0519 (8) | 0.0395 (8) | 0.0761 (11) | 0.0055 (6) | 0.0118 (7) | 0.0083 (7) |
| O2 | 0.0347 (6) | 0.0408 (7) | 0.0531 (9) | 0.0030 (5) | 0.0068 (6) | 0.0007 (6) |
| N1 | 0.0402 (8) | 0.0399 (9) | 0.0575 (11) | 0.0064 (7) | 0.0061 (7) | 0.0015 (7) |
| N2 | 0.0464 (9) | 0.0448 (9) | 0.0615 (12) | 0.0013 (8) | 0.0073 (8) | 0.0058 (8) |
| C1 | 0.0474 (11) | 0.0396 (10) | 0.0477 (12) | −0.0031 (8) | 0.0055 (9) | 0.0040 (8) |
| C2 | 0.0458 (11) | 0.0505 (12) | 0.0527 (13) | −0.0098 (9) | 0.0122 (9) | 0.0030 (9) |
| C3 | 0.0349 (9) | 0.0569 (12) | 0.0472 (12) | −0.0011 (8) | 0.0050 (8) | −0.0066 (9) |
| C4 | 0.0446 (11) | 0.0421 (10) | 0.0550 (13) | 0.0043 (8) | 0.0053 (9) | −0.0002 (9) |
| C5 | 0.0415 (10) | 0.0385 (10) | 0.0488 (12) | −0.0034 (7) | 0.0067 (8) | 0.0025 (8) |
| C6 | 0.0376 (9) | 0.0369 (9) | 0.0380 (11) | −0.0020 (7) | 0.0025 (7) | −0.0035 (7) |
| C7 | 0.0407 (9) | 0.0384 (10) | 0.0393 (11) | −0.0018 (7) | 0.0024 (8) | −0.0039 (7) |
| C8 | 0.0349 (9) | 0.0374 (10) | 0.0511 (12) | −0.0001 (7) | 0.0062 (8) | −0.0050 (8) |
| C9 | 0.0341 (9) | 0.0387 (9) | 0.0428 (11) | 0.0023 (7) | 0.0020 (7) | −0.0067 (8) |
| C10 | 0.0387 (9) | 0.0428 (10) | 0.0441 (12) | −0.0009 (8) | 0.0022 (8) | −0.0023 (8) |
| C11 | 0.0380 (10) | 0.0553 (12) | 0.0466 (12) | −0.0055 (8) | 0.0017 (8) | −0.0023 (9) |
| C12 | 0.0542 (13) | 0.0643 (14) | 0.0652 (16) | −0.0073 (11) | 0.0064 (11) | 0.0097 (12) |
| C13 | 0.0563 (15) | 0.094 (2) | 0.0731 (19) | −0.0240 (15) | 0.0099 (12) | 0.0140 (15) |
| C14 | 0.0358 (11) | 0.115 (2) | 0.0776 (19) | −0.0088 (13) | 0.0123 (11) | −0.0057 (16) |
| C15 | 0.0443 (13) | 0.0813 (19) | 0.121 (3) | 0.0050 (12) | 0.0181 (14) | −0.0089 (17) |
| C16 | 0.0429 (11) | 0.0570 (13) | 0.0939 (19) | −0.0010 (10) | 0.0144 (12) | −0.0044 (13) |
Geometric parameters (Å, º)
| Cl1—C3 | 1.735 (2) | C5—C6 | 1.396 (3) |
| Cl2—C14 | 1.740 (2) | C5—H5A | 0.9300 |
| S1—C9 | 1.7279 (19) | C6—C7 | 1.483 (2) |
| S1—C8 | 1.8014 (18) | C7—C8 | 1.512 (2) |
| O1—C7 | 1.219 (2) | C8—H8A | 0.9700 |
| O2—C9 | 1.364 (2) | C8—H8B | 0.9700 |
| O2—C10 | 1.366 (2) | C10—C11 | 1.459 (3) |
| N1—C9 | 1.277 (2) | C11—C16 | 1.376 (3) |
| N1—N2 | 1.424 (2) | C11—C12 | 1.390 (3) |
| N2—C10 | 1.281 (3) | C12—C13 | 1.373 (3) |
| C1—C2 | 1.372 (3) | C12—H12A | 0.9300 |
| C1—C6 | 1.394 (3) | C13—C14 | 1.369 (4) |
| C1—H1B | 0.9300 | C13—H13A | 0.9300 |
| C2—C3 | 1.384 (3) | C14—C15 | 1.370 (4) |
| C2—H2B | 0.9300 | C15—C16 | 1.385 (3) |
| C3—C4 | 1.381 (3) | C15—H15A | 0.9300 |
| C4—C5 | 1.375 (3) | C16—H16A | 0.9300 |
| C4—H4A | 0.9300 | ||
| C9—S1—C8 | 100.05 (9) | C7—C8—H8B | 110.8 |
| C9—O2—C10 | 101.97 (14) | S1—C8—H8B | 110.8 |
| C9—N1—N2 | 105.12 (15) | H8A—C8—H8B | 108.9 |
| C10—N2—N1 | 106.51 (16) | N1—C9—O2 | 113.80 (16) |
| C2—C1—C6 | 121.04 (18) | N1—C9—S1 | 131.81 (14) |
| C2—C1—H1B | 119.5 | O2—C9—S1 | 114.39 (13) |
| C6—C1—H1B | 119.5 | N2—C10—O2 | 112.59 (17) |
| C1—C2—C3 | 118.81 (18) | N2—C10—C11 | 128.91 (19) |
| C1—C2—H2B | 120.6 | O2—C10—C11 | 118.50 (17) |
| C3—C2—H2B | 120.6 | C16—C11—C12 | 119.5 (2) |
| C4—C3—C2 | 121.32 (18) | C16—C11—C10 | 121.17 (19) |
| C4—C3—Cl1 | 119.47 (17) | C12—C11—C10 | 119.4 (2) |
| C2—C3—Cl1 | 119.20 (16) | C13—C12—C11 | 120.2 (3) |
| C5—C4—C3 | 119.66 (19) | C13—C12—H12A | 119.9 |
| C5—C4—H4A | 120.2 | C11—C12—H12A | 119.9 |
| C3—C4—H4A | 120.2 | C14—C13—C12 | 119.5 (2) |
| C4—C5—C6 | 120.09 (18) | C14—C13—H13A | 120.3 |
| C4—C5—H5A | 120.0 | C12—C13—H13A | 120.3 |
| C6—C5—H5A | 120.0 | C13—C14—C15 | 121.4 (2) |
| C1—C6—C5 | 119.08 (17) | C13—C14—Cl2 | 119.2 (2) |
| C1—C6—C7 | 117.65 (17) | C15—C14—Cl2 | 119.4 (2) |
| C5—C6—C7 | 123.26 (17) | C14—C15—C16 | 119.2 (3) |
| O1—C7—C6 | 120.85 (17) | C14—C15—H15A | 120.4 |
| O1—C7—C8 | 119.29 (17) | C16—C15—H15A | 120.4 |
| C6—C7—C8 | 119.85 (16) | C11—C16—C15 | 120.3 (2) |
| C7—C8—S1 | 104.72 (12) | C11—C16—H16A | 119.9 |
| C7—C8—H8A | 110.8 | C15—C16—H16A | 119.9 |
| S1—C8—H8A | 110.8 | ||
| C9—N1—N2—C10 | 0.2 (2) | C10—O2—C9—S1 | 179.80 (13) |
| C6—C1—C2—C3 | 0.1 (3) | C8—S1—C9—N1 | −11.3 (2) |
| C1—C2—C3—C4 | −0.5 (3) | C8—S1—C9—O2 | 169.15 (14) |
| C1—C2—C3—Cl1 | −179.61 (17) | N1—N2—C10—O2 | −0.1 (2) |
| C2—C3—C4—C5 | 0.5 (3) | N1—N2—C10—C11 | 179.0 (2) |
| Cl1—C3—C4—C5 | 179.62 (16) | C9—O2—C10—N2 | 0.0 (2) |
| C3—C4—C5—C6 | −0.1 (3) | C9—O2—C10—C11 | −179.28 (17) |
| C2—C1—C6—C5 | 0.3 (3) | N2—C10—C11—C16 | −166.0 (2) |
| C2—C1—C6—C7 | −178.44 (19) | O2—C10—C11—C16 | 13.1 (3) |
| C4—C5—C6—C1 | −0.3 (3) | N2—C10—C11—C12 | 13.5 (4) |
| C4—C5—C6—C7 | 178.38 (18) | O2—C10—C11—C12 | −167.4 (2) |
| C1—C6—C7—O1 | −0.2 (3) | C16—C11—C12—C13 | 0.5 (4) |
| C5—C6—C7—O1 | −178.9 (2) | C10—C11—C12—C13 | −179.1 (2) |
| C1—C6—C7—C8 | 179.18 (17) | C11—C12—C13—C14 | 0.3 (4) |
| C5—C6—C7—C8 | 0.5 (3) | C12—C13—C14—C15 | −0.6 (5) |
| O1—C7—C8—S1 | 4.4 (2) | C12—C13—C14—Cl2 | 179.0 (2) |
| C6—C7—C8—S1 | −174.98 (14) | C13—C14—C15—C16 | 0.1 (5) |
| C9—S1—C8—C7 | 176.28 (13) | Cl2—C14—C15—C16 | −179.4 (2) |
| N2—N1—C9—O2 | −0.2 (2) | C12—C11—C16—C15 | −0.9 (4) |
| N2—N1—C9—S1 | −179.78 (16) | C10—C11—C16—C15 | 178.6 (2) |
| C10—O2—C9—N1 | 0.2 (2) | C14—C15—C16—C11 | 0.6 (5) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C1—H1B···N1i | 0.93 | 2.48 | 3.353 (3) | 157 |
Symmetry code: (i) −x, y−1/2, −z+1/2.
References
- Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
- Chohan, Z. H., Pervez, H., Rauf, A., Khan, K. M. & Supuran, C. T. (2006). J. Enzyme Inhib. Med. Chem. 21, 193–201. [DOI] [PubMed]
- Fadda, A., Abdel-Rahman, A.-H., El-Sayed, W., Zidan, T. & Badria, F. (2011). Chem. Heterocycl. Compd, 47, 856–864.
- Jakobi, H., Ort, O., Schaper, W., Braun, R., Krautstrunk, G., Markl, M. & Bonin, W. (1999). US Patent No. 5925644.
- Jha, K. K., Samad, A., Kumar, Y., Shaharyar, M., Khosa, R., Jaim, J. & Bansal, S. (2009). Iran. J. Pharm. Res. 8, 163–167.
- Kashtoh, H., Hussain, S., Khan, A., Saad, S. M., Khan, J. A., Khan, K. M., Perveen, S. & Choudhary, M. I. (2014). Bioorg. Med. Chem. 22, 5454–5465. [DOI] [PubMed]
- Khan, M. T. H., Choudhary, M. I., Khan, K. M., Rani, M. & Atta-ur-Rahman (2005). Bioorg. Med. Chem. 13, 3385–3395. [DOI] [PubMed]
- Khan, K. M., Rahim, F., Halim, S. A., Taha, M., Khan, M., Perveen, S., Zaheer-ul-Haq, Mesaik, M. A. & Iqbal Choudhary, M. (2011). Bioorg. Med. Chem. 19, 4286–4294. [DOI] [PubMed]
- Loetchutinat, C., Chau, F. & Mankhetkorn, S. (2003). Chem. Pharm. Bull. 51, 728–730. [DOI] [PubMed]
- Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
- Palaska, E., Şahin, G., Kelicen, P., Durlu, N. T. & Altinok, G. (2002). Farmaco, 57, 101–107. [DOI] [PubMed]
- Şahin, G., Palaska, E., Ekizoğlu, M. & Özalp, M. (2002). Farmaco, 57, 539–542. [DOI] [PubMed]
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19–32.
- Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
- Tyagi, M. & Kumar, A. (2002). Orient. J. Chem. 18, 125–130.
- Vitaku, E., Smith, D. T. & Njardarson, J. T. (2014). J. Med. Chem. 57, 10257–10274. [DOI] [PubMed]
- Xia, C.-H., Mao, C.-B. & Wu, B.-L. (2011). Acta Cryst. E67, o413. [DOI] [PMC free article] [PubMed]
- Xu, L.-Z., Yu, G.-P., Yin, S.-M., Zhou, K. & Yang, S.-H. (2005). Acta Cryst. E61, o3375–o3376.
- Zhang, X.-M., Qiu, M., Sun, J., Zhang, Y.-B., Yang, Y.-S., Wang, X.-L., Tang, J.-F. & Zhu, H.-L. (2011). Bioorg. Med. Chem. 19, 6518–6524. [DOI] [PubMed]
- Zou, X., Zhang, Z. & Jin, G. (2002). J. Chem. Res. (S), pp. 228–230.
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/S2056989017003978/rz5206sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017003978/rz5206Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989017003978/rz5206Isup3.cml
CCDC reference: 1537363
Additional supporting information: crystallographic information; 3D view; checkCIF report