organic compounds
N′-[(1E)-1-(4-Chlorophenyl)ethylidene]-2-(2,3-dimethylanilino)benzohydrazide
aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, eDepartment of Chemistry, College of Education, Kirkuk University, Kirkuk, Iraq, and fNational Organization for Drug Control and Research, Giza, Egypt
*Correspondence e-mail: shaabankamel@yahoo.com
In the title compound, C23H22ClN3O, the dihedral angle between the planes of the chlorophenyl and dimethylphenyl rings is 62.49 (10)°. These rings make dihedral angles of 21.11 (9) and 59.85 (9)°, respectively, with the central benzene ring. In the crystal, molecules are linked into a three-dimensional supramolecular network by N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds, and weak C—H⋯π interactions.
Keywords: crystal structure; mefenamic acid; non-steroidal anti-inflammatory drug; NSAID; hydrazone.
CCDC reference: 1569207
Structure description
Mefenamic acid (MA), or 2-[(2,3-dimethylphenyl)amino]benzoic acid, belongs to the family of N-arylanthranilic acids. It is one of the most widely used non-steroidal anti-inflammatory drugs (NSAIDs), having both anti-inflammatory and analgesic activities (Arun & Ashok, 2009). NSAIDs are associated with gastrointestinal ulcers, serious cardiovascular events and hypertension (Gupta & Kulkarni, 2013). Recently, it was found that masking the carboxylic acid group in the parent drug of NSAIDs led to safer prodrug profiles and enhanced the pharmacophoric efficacy (Mague et al., 2014). In addition, some evidence showed that the hydrazone group present in the anti-inflammatory drug structure is behind its inhibitory character (Mohamed et al., 2012). Further to our ongoing study of the functionalization of NSAIDs (Mohamed et al., 2015a,b), the title compound was synthesized as a hydrazone profile incorporating MA as a core structure without a free carboxylic group.
The title molecule (Fig. 1) is twisted, with the dihedral angle between the planes of the chlorophenyl and dimethylphenyl rings being 62.49 (10)°. The chlorophenyl and dimethylphenyl rings make dihedral angles of 21.11 (9) and 59.85 (9)° with the central benzene ring, respectively. The bridging fragment (C1/N1/N2/O1/C8) is not planar, with an N1—N2—C8—O1 torsion angle of 5.0 (2)°. All bond lengths and angles (Table 1) are comparable with those of related structures (Zhen & Han, 2005; Chantrapromma et al., 2014; Fun et al., 2011; Horkaew et al., 2012).
In the crystal (Fig. 2), molecules are linked by N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds (Table 1) into a three-dimensional network. Weak C—H⋯π interactions (Table 1) are also present.
Synthesis and crystallization
The title compound was synthesized according to our previously reported procedure (Mohamed et al., 2015a). The product was recrystallized from ethanol solution to yield yellow blocks of (I) (m.p. 473–477 K).
Refinement
Crystal data, data collection and structure . H atoms on C atoms were placed in calculated positions and allowed to ride on their carrier atoms, with aromatic C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C), and methyl C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C). H atoms on N atoms were found in a difference Fourier map and were refined, with the N—H distances restrained to 0.86 (2) Å and with Uiso(H) = 1.2Ueq(N).
details are summarized in Table 2
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Structural data
CCDC reference: 1569207
https://doi.org/10.1107/S2414314617011889/xu4031sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617011889/xu4031Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617011889/xu4031Isup3.cml
Data collection: CrysAlis PRO (Agilent, 2014); cell
CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and WinGX (Farrugia, 2012).C23H22ClN3O | F(000) = 824 |
Mr = 391.88 | Dx = 1.281 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 13.1089 (4) Å | Cell parameters from 3019 reflections |
b = 19.6738 (6) Å | θ = 4.1–71.1° |
c = 7.9333 (2) Å | µ = 1.80 mm−1 |
β = 96.899 (2)° | T = 173 K |
V = 2031.20 (10) Å3 | Prism, colourless |
Z = 4 | 0.45 × 0.25 × 0.10 mm |
Rigaku Oxford Gemini diffractometer | 3854 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source | 3295 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 71.4°, θmin = 4.1° |
ω scans | h = −15→16 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −23→9 |
Tmin = 0.749, Tmax = 1.000 | l = −9→9 |
7509 measured reflections |
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0717P)2 + 0.6046P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
3854 reflections | Δρmax = 0.37 e Å−3 |
262 parameters | Δρmin = −0.40 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.38673 (13) | 0.82927 (9) | 0.6434 (2) | 0.0373 (4) | |
C2 | 0.45079 (13) | 0.84964 (9) | 0.5093 (2) | 0.0380 (4) | |
C3 | 0.51538 (14) | 0.80264 (11) | 0.4452 (2) | 0.0450 (4) | |
H3A | 0.5221 | 0.7583 | 0.4928 | 0.054* | |
C4 | 0.57021 (15) | 0.82006 (13) | 0.3121 (3) | 0.0554 (5) | |
H4 | 0.6157 | 0.7884 | 0.2701 | 0.066* | |
C5 | 0.55760 (17) | 0.88399 (14) | 0.2419 (3) | 0.0583 (6) | |
C6 | 0.49458 (18) | 0.93127 (12) | 0.3018 (3) | 0.0574 (6) | |
H6 | 0.4866 | 0.9750 | 0.2510 | 0.069* | |
C7 | 0.44242 (16) | 0.91431 (10) | 0.4382 (2) | 0.0478 (5) | |
H7 | 0.4004 | 0.9473 | 0.4836 | 0.057* | |
C8 | 0.24073 (13) | 0.68585 (8) | 0.70860 (18) | 0.0315 (3) | |
C9 | 0.17766 (12) | 0.65811 (8) | 0.83703 (19) | 0.0320 (3) | |
C10 | 0.12799 (13) | 0.70152 (9) | 0.9389 (2) | 0.0353 (4) | |
H10 | 0.1363 | 0.7492 | 0.9281 | 0.042* | |
C11 | 0.06683 (14) | 0.67704 (9) | 1.0554 (2) | 0.0397 (4) | |
H11 | 0.0332 | 0.7074 | 1.1236 | 0.048* | |
C12 | 0.05530 (14) | 0.60724 (10) | 1.0711 (2) | 0.0413 (4) | |
H12 | 0.0145 | 0.5898 | 1.1525 | 0.050* | |
C13 | 0.10221 (14) | 0.56296 (9) | 0.9703 (2) | 0.0384 (4) | |
H13 | 0.0934 | 0.5154 | 0.9834 | 0.046* | |
C14 | 0.16279 (13) | 0.58687 (8) | 0.8485 (2) | 0.0343 (4) | |
C15 | 0.19282 (13) | 0.47261 (8) | 0.7284 (2) | 0.0359 (4) | |
C16 | 0.22356 (15) | 0.43079 (11) | 0.8668 (2) | 0.0477 (4) | |
H16 | 0.2523 | 0.4500 | 0.9716 | 0.057* | |
C17 | 0.21207 (16) | 0.36117 (11) | 0.8509 (3) | 0.0533 (5) | |
H17 | 0.2322 | 0.3325 | 0.9454 | 0.064* | |
C18 | 0.17132 (16) | 0.33337 (9) | 0.6975 (3) | 0.0509 (5) | |
H18 | 0.1636 | 0.2855 | 0.6878 | 0.061* | |
C19 | 0.14150 (15) | 0.37399 (9) | 0.5579 (3) | 0.0435 (4) | |
C20 | 0.15184 (12) | 0.44481 (8) | 0.5730 (2) | 0.0347 (4) | |
C21 | 0.1000 (2) | 0.34189 (12) | 0.3907 (3) | 0.0730 (7) | |
H21A | 0.1014 | 0.2923 | 0.4023 | 0.110* | |
H21B | 0.1426 | 0.3555 | 0.3030 | 0.110* | |
H21C | 0.0291 | 0.3570 | 0.3583 | 0.110* | |
C22 | 0.12136 (16) | 0.49003 (10) | 0.4219 (2) | 0.0464 (4) | |
H22A | 0.1805 | 0.4967 | 0.3590 | 0.070* | |
H22B | 0.0985 | 0.5341 | 0.4608 | 0.070* | |
H22C | 0.0653 | 0.4687 | 0.3475 | 0.070* | |
C23 | 0.3623 (2) | 0.87996 (12) | 0.7733 (3) | 0.0633 (7) | |
H23A | 0.3985 | 0.9226 | 0.7571 | 0.095* | |
H23B | 0.3844 | 0.8622 | 0.8873 | 0.095* | |
H23C | 0.2881 | 0.8883 | 0.7608 | 0.095* | |
Cl1 | 0.62355 (6) | 0.90513 (5) | 0.07017 (9) | 0.0951 (3) | |
N1 | 0.35227 (10) | 0.76846 (7) | 0.62931 (16) | 0.0322 (3) | |
N2 | 0.29092 (11) | 0.74519 (7) | 0.74680 (16) | 0.0317 (3) | |
H2N | 0.2954 (16) | 0.7615 (10) | 0.848 (2) | 0.038* | |
N3 | 0.20736 (14) | 0.54361 (8) | 0.7410 (2) | 0.0445 (4) | |
H3N | 0.2270 (18) | 0.5635 (11) | 0.654 (2) | 0.053* | |
O1 | 0.24471 (11) | 0.65752 (6) | 0.57097 (15) | 0.0424 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0380 (8) | 0.0442 (9) | 0.0299 (8) | −0.0101 (7) | 0.0051 (6) | −0.0016 (7) |
C2 | 0.0337 (8) | 0.0489 (10) | 0.0317 (8) | −0.0158 (7) | 0.0049 (6) | −0.0047 (7) |
C3 | 0.0376 (9) | 0.0576 (11) | 0.0402 (9) | −0.0108 (8) | 0.0059 (7) | −0.0053 (8) |
C4 | 0.0373 (9) | 0.0833 (15) | 0.0475 (11) | −0.0155 (10) | 0.0129 (8) | −0.0152 (11) |
C5 | 0.0458 (11) | 0.0896 (16) | 0.0419 (10) | −0.0328 (11) | 0.0151 (8) | −0.0010 (11) |
C6 | 0.0599 (12) | 0.0634 (13) | 0.0506 (11) | −0.0254 (11) | 0.0140 (10) | 0.0083 (10) |
C7 | 0.0498 (10) | 0.0492 (10) | 0.0463 (10) | −0.0161 (8) | 0.0136 (8) | −0.0008 (8) |
C8 | 0.0395 (8) | 0.0310 (7) | 0.0240 (7) | −0.0002 (6) | 0.0043 (6) | 0.0035 (6) |
C9 | 0.0359 (8) | 0.0362 (8) | 0.0238 (7) | −0.0069 (6) | 0.0026 (6) | 0.0006 (6) |
C10 | 0.0420 (9) | 0.0348 (8) | 0.0291 (7) | −0.0071 (7) | 0.0038 (6) | −0.0025 (6) |
C11 | 0.0436 (9) | 0.0442 (9) | 0.0328 (8) | −0.0043 (7) | 0.0110 (7) | −0.0043 (7) |
C12 | 0.0443 (9) | 0.0493 (10) | 0.0321 (8) | −0.0109 (8) | 0.0115 (7) | 0.0023 (7) |
C13 | 0.0461 (9) | 0.0366 (8) | 0.0333 (8) | −0.0101 (7) | 0.0073 (7) | 0.0026 (7) |
C14 | 0.0402 (8) | 0.0356 (8) | 0.0269 (7) | −0.0070 (7) | 0.0034 (6) | −0.0008 (6) |
C15 | 0.0376 (8) | 0.0324 (8) | 0.0387 (8) | −0.0022 (7) | 0.0092 (7) | 0.0021 (7) |
C16 | 0.0487 (10) | 0.0509 (10) | 0.0420 (9) | −0.0057 (8) | −0.0006 (8) | 0.0085 (8) |
C17 | 0.0514 (11) | 0.0458 (10) | 0.0626 (13) | 0.0074 (9) | 0.0058 (9) | 0.0233 (9) |
C18 | 0.0529 (11) | 0.0295 (8) | 0.0730 (14) | 0.0021 (8) | 0.0186 (10) | 0.0049 (9) |
C19 | 0.0419 (9) | 0.0353 (9) | 0.0543 (11) | −0.0030 (7) | 0.0092 (8) | −0.0044 (8) |
C20 | 0.0296 (7) | 0.0343 (8) | 0.0407 (9) | 0.0021 (6) | 0.0069 (6) | 0.0013 (7) |
C21 | 0.0935 (19) | 0.0511 (13) | 0.0728 (16) | −0.0187 (13) | 0.0027 (14) | −0.0197 (12) |
C22 | 0.0506 (10) | 0.0464 (10) | 0.0416 (9) | 0.0018 (8) | 0.0026 (8) | 0.0041 (8) |
C23 | 0.0870 (17) | 0.0562 (12) | 0.0537 (12) | −0.0331 (12) | 0.0376 (12) | −0.0182 (10) |
Cl1 | 0.0815 (5) | 0.1470 (8) | 0.0648 (4) | −0.0449 (5) | 0.0413 (3) | 0.0049 (4) |
N1 | 0.0324 (7) | 0.0400 (7) | 0.0243 (6) | −0.0044 (6) | 0.0046 (5) | 0.0042 (5) |
N2 | 0.0372 (7) | 0.0375 (7) | 0.0210 (6) | −0.0062 (6) | 0.0059 (5) | 0.0020 (5) |
N3 | 0.0661 (10) | 0.0332 (7) | 0.0379 (8) | −0.0106 (7) | 0.0215 (7) | −0.0013 (6) |
O1 | 0.0654 (8) | 0.0355 (6) | 0.0289 (6) | −0.0076 (6) | 0.0161 (5) | −0.0023 (5) |
C1—N1 | 1.279 (2) | C13—H13 | 0.9500 |
C1—C2 | 1.487 (2) | C14—N3 | 1.383 (2) |
C1—C23 | 1.496 (3) | C15—C16 | 1.392 (3) |
C2—C3 | 1.391 (3) | C15—C20 | 1.396 (2) |
C2—C7 | 1.391 (3) | C15—N3 | 1.412 (2) |
C3—C4 | 1.390 (3) | C16—C17 | 1.382 (3) |
C3—H3A | 0.9500 | C16—H16 | 0.9500 |
C4—C5 | 1.377 (4) | C17—C18 | 1.382 (3) |
C4—H4 | 0.9500 | C17—H17 | 0.9500 |
C5—C6 | 1.366 (4) | C18—C19 | 1.384 (3) |
C5—Cl1 | 1.749 (2) | C18—H18 | 0.9500 |
C6—C7 | 1.389 (3) | C19—C20 | 1.404 (2) |
C6—H6 | 0.9500 | C19—C21 | 1.510 (3) |
C7—H7 | 0.9500 | C20—C22 | 1.508 (2) |
C8—O1 | 1.2325 (19) | C21—H21A | 0.9800 |
C8—N2 | 1.356 (2) | C21—H21B | 0.9800 |
C8—C9 | 1.491 (2) | C21—H21C | 0.9800 |
C9—C10 | 1.390 (2) | C22—H22A | 0.9800 |
C9—C14 | 1.419 (2) | C22—H22B | 0.9800 |
C10—C11 | 1.381 (2) | C22—H22C | 0.9800 |
C10—H10 | 0.9500 | C23—H23A | 0.9800 |
C11—C12 | 1.389 (3) | C23—H23B | 0.9800 |
C11—H11 | 0.9500 | C23—H23C | 0.9800 |
C12—C13 | 1.377 (3) | N1—N2 | 1.3804 (18) |
C12—H12 | 0.9500 | N2—H2N | 0.859 (15) |
C13—C14 | 1.403 (2) | N3—H3N | 0.861 (16) |
N1—C1—C2 | 114.40 (15) | C16—C15—N3 | 120.34 (17) |
N1—C1—C23 | 125.56 (16) | C20—C15—N3 | 118.98 (15) |
C2—C1—C23 | 119.93 (16) | C17—C16—C15 | 119.74 (19) |
C3—C2—C7 | 118.80 (17) | C17—C16—H16 | 120.1 |
C3—C2—C1 | 120.22 (17) | C15—C16—H16 | 120.1 |
C7—C2—C1 | 120.85 (17) | C18—C17—C16 | 119.91 (18) |
C4—C3—C2 | 120.5 (2) | C18—C17—H17 | 120.0 |
C4—C3—H3A | 119.8 | C16—C17—H17 | 120.0 |
C2—C3—H3A | 119.8 | C17—C18—C19 | 121.24 (17) |
C5—C4—C3 | 119.0 (2) | C17—C18—H18 | 119.4 |
C5—C4—H4 | 120.5 | C19—C18—H18 | 119.4 |
C3—C4—H4 | 120.5 | C18—C19—C20 | 119.34 (18) |
C6—C5—C4 | 121.96 (19) | C18—C19—C21 | 119.94 (19) |
C6—C5—Cl1 | 119.00 (19) | C20—C19—C21 | 120.71 (19) |
C4—C5—Cl1 | 119.04 (19) | C15—C20—C19 | 119.15 (16) |
C5—C6—C7 | 118.8 (2) | C15—C20—C22 | 120.55 (15) |
C5—C6—H6 | 120.6 | C19—C20—C22 | 120.29 (17) |
C7—C6—H6 | 120.6 | C19—C21—H21A | 109.5 |
C6—C7—C2 | 120.9 (2) | C19—C21—H21B | 109.5 |
C6—C7—H7 | 119.5 | H21A—C21—H21B | 109.5 |
C2—C7—H7 | 119.5 | C19—C21—H21C | 109.5 |
O1—C8—N2 | 121.07 (14) | H21A—C21—H21C | 109.5 |
O1—C8—C9 | 121.73 (14) | H21B—C21—H21C | 109.5 |
N2—C8—C9 | 117.16 (13) | C20—C22—H22A | 109.5 |
C10—C9—C14 | 119.45 (15) | C20—C22—H22B | 109.5 |
C10—C9—C8 | 120.62 (14) | H22A—C22—H22B | 109.5 |
C14—C9—C8 | 119.81 (15) | C20—C22—H22C | 109.5 |
C11—C10—C9 | 121.66 (16) | H22A—C22—H22C | 109.5 |
C11—C10—H10 | 119.2 | H22B—C22—H22C | 109.5 |
C9—C10—H10 | 119.2 | C1—C23—H23A | 109.5 |
C10—C11—C12 | 118.90 (16) | C1—C23—H23B | 109.5 |
C10—C11—H11 | 120.5 | H23A—C23—H23B | 109.5 |
C12—C11—H11 | 120.5 | C1—C23—H23C | 109.5 |
C13—C12—C11 | 120.82 (16) | H23A—C23—H23C | 109.5 |
C13—C12—H12 | 119.6 | H23B—C23—H23C | 109.5 |
C11—C12—H12 | 119.6 | C1—N1—N2 | 118.65 (14) |
C12—C13—C14 | 121.14 (16) | C8—N2—N1 | 116.17 (13) |
C12—C13—H13 | 119.4 | C8—N2—H2N | 120.5 (14) |
C14—C13—H13 | 119.4 | N1—N2—H2N | 121.7 (14) |
N3—C14—C13 | 122.27 (15) | C14—N3—C15 | 126.10 (15) |
N3—C14—C9 | 119.78 (15) | C14—N3—H3N | 113.8 (16) |
C13—C14—C9 | 117.94 (15) | C15—N3—H3N | 116.4 (16) |
C16—C15—C20 | 120.61 (16) | ||
N1—C1—C2—C3 | −35.9 (2) | C8—C9—C14—N3 | 0.3 (2) |
C23—C1—C2—C3 | 147.8 (2) | C10—C9—C14—C13 | −3.4 (2) |
N1—C1—C2—C7 | 139.95 (17) | C8—C9—C14—C13 | −179.50 (15) |
C23—C1—C2—C7 | −36.4 (3) | C20—C15—C16—C17 | −0.9 (3) |
C7—C2—C3—C4 | −0.2 (3) | N3—C15—C16—C17 | −177.81 (18) |
C1—C2—C3—C4 | 175.68 (16) | C15—C16—C17—C18 | 0.8 (3) |
C2—C3—C4—C5 | −1.6 (3) | C16—C17—C18—C19 | 0.0 (3) |
C3—C4—C5—C6 | 1.5 (3) | C17—C18—C19—C20 | −0.7 (3) |
C3—C4—C5—Cl1 | −178.09 (15) | C17—C18—C19—C21 | 178.3 (2) |
C4—C5—C6—C7 | 0.5 (3) | C16—C15—C20—C19 | 0.3 (3) |
Cl1—C5—C6—C7 | −179.95 (16) | N3—C15—C20—C19 | 177.20 (16) |
C5—C6—C7—C2 | −2.4 (3) | C16—C15—C20—C22 | −178.26 (17) |
C3—C2—C7—C6 | 2.2 (3) | N3—C15—C20—C22 | −1.3 (2) |
C1—C2—C7—C6 | −173.65 (17) | C18—C19—C20—C15 | 0.5 (3) |
O1—C8—C9—C10 | −144.71 (17) | C21—C19—C20—C15 | −178.4 (2) |
N2—C8—C9—C10 | 32.9 (2) | C18—C19—C20—C22 | 179.07 (18) |
O1—C8—C9—C14 | 31.3 (2) | C21—C19—C20—C22 | 0.1 (3) |
N2—C8—C9—C14 | −151.01 (15) | C2—C1—N1—N2 | −179.22 (14) |
C14—C9—C10—C11 | 2.1 (2) | C23—C1—N1—N2 | −3.2 (3) |
C8—C9—C10—C11 | 178.15 (15) | O1—C8—N2—N1 | −5.0 (2) |
C9—C10—C11—C12 | 0.3 (3) | C9—C8—N2—N1 | 177.36 (13) |
C10—C11—C12—C13 | −1.3 (3) | C1—N1—N2—C8 | 167.86 (15) |
C11—C12—C13—C14 | −0.1 (3) | C13—C14—N3—C15 | 5.2 (3) |
C12—C13—C14—N3 | −177.36 (17) | C9—C14—N3—C15 | −174.63 (17) |
C12—C13—C14—C9 | 2.5 (3) | C16—C15—N3—C14 | −63.0 (3) |
C10—C9—C14—N3 | 176.43 (16) | C20—C15—N3—C14 | 120.0 (2) |
Cg2 and Cg3 are the centroids of the C9–C14 and C15–C20 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O1i | 0.86 (2) | 2.53 (2) | 3.3194 (18) | 153 (2) |
N2—H2N···N1i | 0.86 (2) | 2.34 (2) | 3.0563 (18) | 141 (2) |
N3—H3N···O1 | 0.86 (2) | 1.99 (2) | 2.691 (2) | 139 (2) |
C10—H10···O1i | 0.95 | 2.51 | 3.278 (2) | 138 |
C12—H12···Cg3ii | 0.95 | 2.91 | 3.737 (2) | 146 |
C21—H21C···Cg2iii | 0.98 | 2.94 | 3.720 (3) | 138 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, −y+1, −z+2; (iii) −x, −y+1, −z+1. |
Funding information
Funding for this research was provided by: NSF–MRI program (grant No. CHE-1039027), for the purchase of the X-ray diffractometer.
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