organic compounds
1-(4-Nitrophenyl)-2-({4-phenyl-5-[(p-tolyloxy)methyl]-4H-1,2,4-triazol-3-yl}sulfanyl)acetamide
aDepartment of Chemistry, Faculty of Science, Sana'a University, Sana'a, Yemen, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, dChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, and eChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt
*Correspondence e-mail: shaabankamel@yahoo.com
In the 24H21N5O4S, centrosymmetric dimers with an R22(16) ring motif, lying in the (010) plane, are formed as a result of pairwise N—H⋯N hydrogen bonds. These dimers further interact through C—H⋯O and C—H⋯π interactions to construct a complex extended three-dimensional structure.
of the title compound, CKeywords: crystal structure; 4H-1,2,4-triazole ring; dimer; (p-nitrophenyl) carbamoyl compounds; p-tolyloxyphenyltriazole.
CCDC reference: 1507330
Structure description
There are a large number of drugs containing the 1,2,4-triazole nucleus in their structures including ribavirin (antiviral), rizatriptan (antimigraine), estazolam and alprazolam (anxiolytic), letrozole and anastrozole (breast cancer) (Godhani et al., 2015). Others such as Itraconazole, Fluconazole and Posaconazole have been used for the treatment of fungal infections (Godhani et al., 2015). As part of our studies in this area, we report the synthesis and of the title compound.
The molecular conformation of the title compound (Fig. 1) is partially stabilized by an intramolecular C23—H23⋯O2 hydrogen bond (Table 1). The central 4H-1,2,4-triazole ring of the title molecule makes dihedral angles of 42.34 (9), 87.53 (9) and 58.39 (9)°, with the C6–C11 and C12–C17 benzene rings and the C18–C23 phenyl ring, respectively. All bond lengths and bond angles are within normal ranges.
In the crystal, pairs of molecules are linked by pairwise N—H⋯N hydrogen bonds (Fig. 2; Table 1), forming inversion dimers with (16) ring motifs. C—H⋯O and C—H⋯π interactions (Table 1) further connect these dimers, constructing an extended three-dimensional structure.
Synthesis and crystallization
A suspension of 5-(p-tolyloxy)methyl-4-phenyl-1,2,4- triazoline-3-thione (10 mmol), chloro-N-(p-nitrophenyl)- acetamide (10 mol) and anhydrous K2CO3 (2.0 g) in dry acetone (50 ml) was heated under reflux with stirring for 3 h. The hot reaction mixture was filtered to remove K2CO3 and the clear filtrate was evaporated to dryness. The solid residue was crystallized from ethanol solution to afford the title compound. Yield: 92%; m.p. 477 K. IR: 3240 (NH), 1670 (C=O) cm-1. 1H NMR (CDCl3): 9.4 (s, 1H, NH), 6.7–8.3 (m, 13H, ArH), 4.9 (s, 2H, OCH2), 4.0 (s, 2H, SCH2), 2.1 (s, 3H, CH3) p.p.m..
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 1507330
https://doi.org/10.1107/S2414314616015339/sj4062sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616015339/sj4062Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616015339/sj4062Isup3.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: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C24H21N5O4S | Z = 2 |
Mr = 475.52 | F(000) = 496 |
Triclinic, P1 | Dx = 1.427 Mg m−3 |
a = 8.2241 (4) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 12.2161 (7) Å | Cell parameters from 3208 reflections |
c = 12.3952 (8) Å | θ = 4.1–71.5° |
α = 115.507 (6)° | µ = 1.67 mm−1 |
β = 93.532 (4)° | T = 173 K |
γ = 96.914 (4)° | Prism, colourless |
V = 1106.76 (12) Å3 | 0.06 × 0.06 × 0.04 mm |
Rigaku Oxford Diffraction four-circle diffractometer | 4208 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 3685 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 71.4°, θmin = 4.0° |
ω scans | h = −9→8 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −14→13 |
Tmin = 0.867, Tmax = 1.000 | l = −11→15 |
7218 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0525P)2 + 0.2923P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
4208 reflections | Δρmax = 0.27 e Å−3 |
308 parameters | Δρmin = −0.21 e Å−3 |
0 restraints |
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 | ||
S1 | 0.85636 (5) | 0.52431 (4) | 0.73550 (4) | 0.02853 (13) | |
O1 | 0.97273 (15) | 0.31095 (11) | 0.56291 (10) | 0.0278 (3) | |
O2 | 0.45307 (13) | 0.80442 (10) | 1.06977 (10) | 0.0243 (2) | |
O3 | 1.43377 (17) | −0.21534 (12) | 0.47098 (13) | 0.0371 (3) | |
O4 | 1.30848 (18) | −0.22799 (12) | 0.30651 (11) | 0.0371 (3) | |
N1 | 1.14295 (17) | 0.27467 (12) | 0.69315 (12) | 0.0232 (3) | |
H1 | 1.1841 | 0.3065 | 0.7696 | 0.028* | |
N2 | 0.60984 (16) | 0.59879 (11) | 0.87254 (11) | 0.0193 (3) | |
N3 | 0.82466 (16) | 0.57455 (12) | 0.97176 (12) | 0.0228 (3) | |
N4 | 0.70552 (17) | 0.61560 (12) | 1.04921 (12) | 0.0226 (3) | |
N5 | 1.34846 (18) | −0.17518 (13) | 0.41631 (13) | 0.0268 (3) | |
C1 | 1.04125 (18) | 0.34015 (14) | 0.66351 (14) | 0.0210 (3) | |
C2 | 1.0260 (2) | 0.45989 (15) | 0.77194 (14) | 0.0256 (3) | |
H2A | 1.1298 | 0.5190 | 0.7933 | 0.031* | |
H2B | 1.0064 | 0.4437 | 0.8421 | 0.031* | |
C3 | 0.76396 (18) | 0.56551 (13) | 0.86744 (14) | 0.0199 (3) | |
C4 | 0.58071 (18) | 0.62961 (13) | 0.98868 (14) | 0.0197 (3) | |
C5 | 0.42806 (19) | 0.67541 (14) | 1.03736 (14) | 0.0216 (3) | |
H5A | 0.3307 | 0.6324 | 0.9756 | 0.026* | |
H5B | 0.4098 | 0.6612 | 1.1088 | 0.026* | |
C6 | 1.19059 (19) | 0.16297 (14) | 0.61755 (14) | 0.0210 (3) | |
C7 | 1.2798 (2) | 0.10810 (15) | 0.67497 (14) | 0.0238 (3) | |
H7 | 1.3048 | 0.1475 | 0.7603 | 0.029* | |
C8 | 1.3318 (2) | −0.00215 (15) | 0.60955 (15) | 0.0248 (3) | |
H8 | 1.3929 | −0.0390 | 0.6487 | 0.030* | |
C9 | 1.29292 (19) | −0.05829 (14) | 0.48512 (14) | 0.0234 (3) | |
C10 | 1.2067 (2) | −0.00546 (15) | 0.42604 (14) | 0.0254 (3) | |
H10 | 1.1828 | −0.0453 | 0.3407 | 0.030* | |
C11 | 1.1553 (2) | 0.10597 (15) | 0.49199 (14) | 0.0248 (3) | |
H11 | 1.0966 | 0.1433 | 0.4521 | 0.030* | |
C12 | 0.3168 (2) | 0.86318 (15) | 1.09212 (14) | 0.0224 (3) | |
C13 | 0.1555 (2) | 0.80569 (16) | 1.07641 (15) | 0.0258 (3) | |
H13 | 0.1309 | 0.7192 | 1.0488 | 0.031* | |
C14 | 0.0296 (2) | 0.87682 (17) | 1.10171 (16) | 0.0297 (4) | |
H14 | −0.0812 | 0.8372 | 1.0897 | 0.036* | |
C15 | 0.0612 (2) | 1.00335 (17) | 1.14384 (16) | 0.0308 (4) | |
C16 | 0.2244 (2) | 1.05886 (17) | 1.15901 (18) | 0.0351 (4) | |
H16 | 0.2492 | 1.1455 | 1.1877 | 0.042* | |
C17 | 0.3516 (2) | 0.98984 (16) | 1.13290 (17) | 0.0303 (4) | |
H17 | 0.4621 | 1.0291 | 1.1429 | 0.036* | |
C18 | 0.49849 (18) | 0.59151 (14) | 0.77434 (13) | 0.0192 (3) | |
C19 | 0.4528 (2) | 0.47990 (15) | 0.67390 (15) | 0.0247 (3) | |
H19 | 0.4943 | 0.4089 | 0.6693 | 0.030* | |
C20 | 0.3451 (2) | 0.47341 (18) | 0.57963 (15) | 0.0327 (4) | |
H20 | 0.3134 | 0.3976 | 0.5094 | 0.039* | |
C21 | 0.2835 (2) | 0.5773 (2) | 0.58765 (17) | 0.0382 (4) | |
H21 | 0.2090 | 0.5723 | 0.5233 | 0.046* | |
C22 | 0.3302 (2) | 0.68759 (19) | 0.68882 (18) | 0.0359 (4) | |
H22 | 0.2880 | 0.7584 | 0.6937 | 0.043* | |
C23 | 0.4384 (2) | 0.69645 (15) | 0.78381 (15) | 0.0262 (3) | |
H23 | 0.4706 | 0.7725 | 0.8537 | 0.031* | |
C24 | −0.0755 (3) | 1.0801 (2) | 1.1751 (2) | 0.0413 (5) | |
H24A | −0.1814 | 1.0281 | 1.1327 | 0.062* | |
H24B | −0.0541 | 1.1463 | 1.1506 | 0.062* | |
H24C | −0.0797 | 1.1157 | 1.2622 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0298 (2) | 0.0410 (2) | 0.0215 (2) | 0.02142 (17) | 0.00957 (15) | 0.01517 (18) |
O1 | 0.0292 (6) | 0.0312 (6) | 0.0189 (6) | 0.0121 (5) | −0.0009 (4) | 0.0058 (5) |
O2 | 0.0214 (5) | 0.0185 (5) | 0.0281 (6) | 0.0071 (4) | 0.0044 (4) | 0.0047 (5) |
O3 | 0.0416 (7) | 0.0287 (7) | 0.0399 (7) | 0.0170 (5) | 0.0058 (6) | 0.0110 (6) |
O4 | 0.0542 (8) | 0.0279 (6) | 0.0238 (7) | 0.0121 (6) | 0.0136 (6) | 0.0039 (5) |
N1 | 0.0269 (7) | 0.0232 (7) | 0.0152 (6) | 0.0088 (5) | 0.0011 (5) | 0.0035 (5) |
N2 | 0.0209 (6) | 0.0185 (6) | 0.0166 (6) | 0.0079 (5) | 0.0020 (5) | 0.0049 (5) |
N3 | 0.0226 (6) | 0.0247 (7) | 0.0183 (6) | 0.0090 (5) | 0.0019 (5) | 0.0056 (5) |
N4 | 0.0252 (7) | 0.0224 (6) | 0.0169 (6) | 0.0087 (5) | 0.0020 (5) | 0.0045 (5) |
N5 | 0.0291 (7) | 0.0215 (7) | 0.0277 (7) | 0.0059 (5) | 0.0105 (6) | 0.0076 (6) |
C1 | 0.0182 (7) | 0.0231 (8) | 0.0197 (7) | 0.0059 (6) | 0.0038 (5) | 0.0067 (6) |
C2 | 0.0224 (8) | 0.0297 (8) | 0.0207 (8) | 0.0132 (6) | 0.0013 (6) | 0.0054 (7) |
C3 | 0.0201 (7) | 0.0179 (7) | 0.0195 (7) | 0.0076 (5) | 0.0030 (5) | 0.0051 (6) |
C4 | 0.0219 (7) | 0.0173 (7) | 0.0167 (7) | 0.0046 (5) | 0.0015 (5) | 0.0043 (6) |
C5 | 0.0240 (8) | 0.0186 (7) | 0.0198 (7) | 0.0076 (6) | 0.0043 (6) | 0.0051 (6) |
C6 | 0.0205 (7) | 0.0202 (7) | 0.0194 (7) | 0.0046 (5) | 0.0031 (5) | 0.0056 (6) |
C7 | 0.0261 (8) | 0.0261 (8) | 0.0162 (7) | 0.0065 (6) | 0.0020 (6) | 0.0061 (6) |
C8 | 0.0261 (8) | 0.0255 (8) | 0.0236 (8) | 0.0087 (6) | 0.0042 (6) | 0.0102 (7) |
C9 | 0.0245 (8) | 0.0192 (7) | 0.0230 (8) | 0.0050 (6) | 0.0082 (6) | 0.0052 (6) |
C10 | 0.0295 (8) | 0.0252 (8) | 0.0161 (7) | 0.0056 (6) | 0.0043 (6) | 0.0038 (6) |
C11 | 0.0279 (8) | 0.0267 (8) | 0.0186 (8) | 0.0086 (6) | 0.0024 (6) | 0.0079 (6) |
C12 | 0.0240 (8) | 0.0242 (8) | 0.0196 (7) | 0.0109 (6) | 0.0051 (6) | 0.0081 (6) |
C13 | 0.0260 (8) | 0.0263 (8) | 0.0241 (8) | 0.0075 (6) | 0.0044 (6) | 0.0091 (7) |
C14 | 0.0249 (8) | 0.0369 (9) | 0.0295 (9) | 0.0112 (7) | 0.0064 (6) | 0.0146 (8) |
C15 | 0.0352 (9) | 0.0346 (9) | 0.0303 (9) | 0.0193 (7) | 0.0110 (7) | 0.0170 (8) |
C16 | 0.0390 (10) | 0.0255 (9) | 0.0448 (11) | 0.0144 (7) | 0.0116 (8) | 0.0160 (8) |
C17 | 0.0271 (8) | 0.0247 (8) | 0.0386 (10) | 0.0071 (6) | 0.0067 (7) | 0.0123 (7) |
C18 | 0.0174 (7) | 0.0240 (7) | 0.0175 (7) | 0.0075 (5) | 0.0031 (5) | 0.0091 (6) |
C19 | 0.0253 (8) | 0.0249 (8) | 0.0207 (8) | 0.0073 (6) | 0.0032 (6) | 0.0064 (6) |
C20 | 0.0266 (9) | 0.0439 (10) | 0.0188 (8) | 0.0043 (7) | 0.0009 (6) | 0.0064 (7) |
C21 | 0.0315 (9) | 0.0656 (13) | 0.0243 (9) | 0.0183 (9) | 0.0025 (7) | 0.0237 (9) |
C22 | 0.0393 (10) | 0.0481 (11) | 0.0353 (10) | 0.0259 (8) | 0.0113 (8) | 0.0268 (9) |
C23 | 0.0308 (8) | 0.0258 (8) | 0.0258 (8) | 0.0123 (6) | 0.0066 (6) | 0.0125 (7) |
C24 | 0.0420 (11) | 0.0482 (12) | 0.0473 (12) | 0.0285 (9) | 0.0189 (9) | 0.0265 (10) |
S1—C2 | 1.8062 (16) | C9—C10 | 1.381 (2) |
S1—C3 | 1.7440 (15) | C10—H10 | 0.9500 |
O1—C1 | 1.217 (2) | C10—C11 | 1.387 (2) |
O2—C5 | 1.4331 (19) | C11—H11 | 0.9500 |
O2—C12 | 1.3816 (19) | C12—C13 | 1.385 (2) |
O3—N5 | 1.226 (2) | C12—C17 | 1.390 (2) |
O4—N5 | 1.231 (2) | C13—H13 | 0.9500 |
N1—H1 | 0.8800 | C13—C14 | 1.395 (2) |
N1—C1 | 1.360 (2) | C14—H14 | 0.9500 |
N1—C6 | 1.402 (2) | C14—C15 | 1.386 (3) |
N2—C3 | 1.3739 (19) | C15—C16 | 1.392 (3) |
N2—C4 | 1.367 (2) | C15—C24 | 1.513 (2) |
N2—C18 | 1.4415 (19) | C16—H16 | 0.9500 |
N3—N4 | 1.3973 (18) | C16—C17 | 1.389 (2) |
N3—C3 | 1.311 (2) | C17—H17 | 0.9500 |
N4—C4 | 1.305 (2) | C18—C19 | 1.381 (2) |
N5—C9 | 1.460 (2) | C18—C23 | 1.390 (2) |
C1—C2 | 1.528 (2) | C19—H19 | 0.9500 |
C2—H2A | 0.9900 | C19—C20 | 1.390 (2) |
C2—H2B | 0.9900 | C20—H20 | 0.9500 |
C4—C5 | 1.492 (2) | C20—C21 | 1.389 (3) |
C5—H5A | 0.9900 | C21—H21 | 0.9500 |
C5—H5B | 0.9900 | C21—C22 | 1.377 (3) |
C6—C7 | 1.400 (2) | C22—H22 | 0.9500 |
C6—C11 | 1.398 (2) | C22—C23 | 1.388 (3) |
C7—H7 | 0.9500 | C23—H23 | 0.9500 |
C7—C8 | 1.377 (2) | C24—H24A | 0.9800 |
C8—H8 | 0.9500 | C24—H24B | 0.9800 |
C8—C9 | 1.388 (2) | C24—H24C | 0.9800 |
C3—S1—C2 | 99.82 (8) | C9—C10—C11 | 119.64 (15) |
C12—O2—C5 | 117.66 (12) | C11—C10—H10 | 120.2 |
C1—N1—H1 | 115.8 | C6—C11—H11 | 120.3 |
C1—N1—C6 | 128.31 (14) | C10—C11—C6 | 119.48 (15) |
C6—N1—H1 | 115.8 | C10—C11—H11 | 120.3 |
C3—N2—C18 | 127.40 (13) | O2—C12—C13 | 125.17 (15) |
C4—N2—C3 | 104.43 (12) | O2—C12—C17 | 114.73 (15) |
C4—N2—C18 | 127.94 (13) | C13—C12—C17 | 120.10 (15) |
C3—N3—N4 | 106.31 (12) | C12—C13—H13 | 120.5 |
C4—N4—N3 | 107.88 (12) | C12—C13—C14 | 118.91 (16) |
O3—N5—O4 | 123.30 (14) | C14—C13—H13 | 120.5 |
O3—N5—C9 | 118.18 (14) | C13—C14—H14 | 118.9 |
O4—N5—C9 | 118.52 (15) | C15—C14—C13 | 122.12 (16) |
O1—C1—N1 | 125.37 (14) | C15—C14—H14 | 118.9 |
O1—C1—C2 | 122.69 (14) | C14—C15—C16 | 117.81 (16) |
N1—C1—C2 | 111.91 (13) | C14—C15—C24 | 121.68 (18) |
S1—C2—H2A | 109.8 | C16—C15—C24 | 120.49 (17) |
S1—C2—H2B | 109.8 | C15—C16—H16 | 119.4 |
C1—C2—S1 | 109.43 (11) | C17—C16—C15 | 121.14 (17) |
C1—C2—H2A | 109.8 | C17—C16—H16 | 119.4 |
C1—C2—H2B | 109.8 | C12—C17—H17 | 120.0 |
H2A—C2—H2B | 108.2 | C16—C17—C12 | 119.90 (16) |
N2—C3—S1 | 120.49 (11) | C16—C17—H17 | 120.0 |
N3—C3—S1 | 128.51 (12) | C19—C18—N2 | 119.01 (14) |
N3—C3—N2 | 110.95 (13) | C19—C18—C23 | 121.77 (15) |
N2—C4—C5 | 123.61 (14) | C23—C18—N2 | 119.21 (14) |
N4—C4—N2 | 110.42 (13) | C18—C19—H19 | 120.6 |
N4—C4—C5 | 125.95 (14) | C18—C19—C20 | 118.73 (16) |
O2—C5—C4 | 106.51 (12) | C20—C19—H19 | 120.6 |
O2—C5—H5A | 110.4 | C19—C20—H20 | 119.9 |
O2—C5—H5B | 110.4 | C21—C20—C19 | 120.28 (17) |
C4—C5—H5A | 110.4 | C21—C20—H20 | 119.9 |
C4—C5—H5B | 110.4 | C20—C21—H21 | 120.0 |
H5A—C5—H5B | 108.6 | C22—C21—C20 | 120.01 (16) |
C7—C6—N1 | 115.99 (14) | C22—C21—H21 | 120.0 |
C11—C6—N1 | 124.33 (15) | C21—C22—H22 | 119.6 |
C11—C6—C7 | 119.68 (15) | C21—C22—C23 | 120.73 (17) |
C6—C7—H7 | 119.6 | C23—C22—H22 | 119.6 |
C8—C7—C6 | 120.89 (15) | C18—C23—H23 | 120.8 |
C8—C7—H7 | 119.6 | C22—C23—C18 | 118.46 (16) |
C7—C8—H8 | 120.8 | C22—C23—H23 | 120.8 |
C7—C8—C9 | 118.50 (15) | C15—C24—H24A | 109.5 |
C9—C8—H8 | 120.8 | C15—C24—H24B | 109.5 |
C8—C9—N5 | 118.20 (15) | C15—C24—H24C | 109.5 |
C10—C9—N5 | 119.99 (15) | H24A—C24—H24B | 109.5 |
C10—C9—C8 | 121.80 (15) | H24A—C24—H24C | 109.5 |
C9—C10—H10 | 120.2 | H24B—C24—H24C | 109.5 |
O1—C1—C2—S1 | 14.8 (2) | C4—N2—C18—C23 | 61.2 (2) |
O2—C12—C13—C14 | −179.47 (15) | C5—O2—C12—C13 | −5.5 (2) |
O2—C12—C17—C16 | −179.65 (16) | C5—O2—C12—C17 | 174.82 (14) |
O3—N5—C9—C8 | −3.5 (2) | C6—N1—C1—O1 | 0.1 (3) |
O3—N5—C9—C10 | 175.33 (15) | C6—N1—C1—C2 | −177.91 (15) |
O4—N5—C9—C8 | 176.98 (15) | C6—C7—C8—C9 | −0.4 (2) |
O4—N5—C9—C10 | −4.2 (2) | C7—C6—C11—C10 | 1.1 (2) |
N1—C1—C2—S1 | −167.16 (11) | C7—C8—C9—N5 | −179.99 (15) |
N1—C6—C7—C8 | 179.55 (15) | C7—C8—C9—C10 | 1.2 (2) |
N1—C6—C11—C10 | −179.18 (15) | C8—C9—C10—C11 | −0.8 (3) |
N2—C4—C5—O2 | −82.51 (17) | C9—C10—C11—C6 | −0.4 (2) |
N2—C18—C19—C20 | 179.83 (14) | C11—C6—C7—C8 | −0.7 (2) |
N2—C18—C23—C22 | −179.48 (15) | C12—O2—C5—C4 | 165.95 (13) |
N3—N4—C4—N2 | 0.43 (17) | C12—C13—C14—C15 | −1.0 (3) |
N3—N4—C4—C5 | −178.18 (14) | C13—C12—C17—C16 | 0.6 (3) |
N4—N3—C3—S1 | 177.46 (12) | C13—C14—C15—C16 | 0.9 (3) |
N4—N3—C3—N2 | 0.00 (17) | C13—C14—C15—C24 | −177.84 (17) |
N4—C4—C5—O2 | 95.93 (18) | C14—C15—C16—C17 | 0.0 (3) |
N5—C9—C10—C11 | −179.59 (14) | C15—C16—C17—C12 | −0.7 (3) |
C1—N1—C6—C7 | −172.03 (15) | C17—C12—C13—C14 | 0.2 (2) |
C1—N1—C6—C11 | 8.3 (3) | C18—N2—C3—S1 | 7.8 (2) |
C2—S1—C3—N2 | −168.01 (12) | C18—N2—C3—N3 | −174.54 (14) |
C2—S1—C3—N3 | 14.74 (16) | C18—N2—C4—N4 | 174.33 (14) |
C3—S1—C2—C1 | 135.78 (12) | C18—N2—C4—C5 | −7.0 (2) |
C3—N2—C4—N4 | −0.42 (17) | C18—C19—C20—C21 | −0.8 (3) |
C3—N2—C4—C5 | 178.23 (14) | C19—C18—C23—C22 | −0.3 (2) |
C3—N2—C18—C19 | 55.5 (2) | C19—C20—C21—C22 | 0.6 (3) |
C3—N2—C18—C23 | −125.25 (17) | C20—C21—C22—C23 | −0.2 (3) |
C3—N3—N4—C4 | −0.26 (17) | C21—C22—C23—C18 | 0.1 (3) |
C4—N2—C3—S1 | −177.45 (11) | C23—C18—C19—C20 | 0.6 (2) |
C4—N2—C3—N3 | 0.25 (17) | C24—C15—C16—C17 | 178.74 (18) |
C4—N2—C18—C19 | −118.08 (17) |
Cg1, Cg3 and Cg4 are the centroids of the 4H-1,2,4-triazole ring (N2/C3/N3/N4/C4), the benzene ring (C12–C17) and the phenyl ring (C18–C23), respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N4i | 0.88 | 2.12 | 2.9949 (19) | 177 |
C5—H5B···O4ii | 0.99 | 2.49 | 3.2838 (19) | 137 |
C7—H7···O2i | 0.95 | 2.62 | 3.413 (2) | 141 |
C19—H19···O3iii | 0.95 | 2.43 | 3.236 (2) | 143 |
C23—H23···O2 | 0.95 | 2.55 | 3.194 (2) | 125 |
C2—H2A···Cg4iv | 0.99 | 2.85 | 3.6592 (19) | 140 |
C5—H5B···Cg1v | 0.99 | 2.92 | 3.433 (2) | 113 |
C10—H10···Cg3vi | 0.95 | 2.67 | 3.5536 (18) | 156 |
C14—H14···Cg1vii | 0.95 | 2.98 | 3.781 (2) | 143 |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x−1, y+1, z+1; (iii) −x+2, −y, −z+1; (iv) x+1, y, z; (v) −x+1, −y+1, −z+2; (vi) x+1, y−1, z−1; (vii) x−1, y, z. |
Acknowledgements
JPJ would like to acknowledge the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X ray diffractometer.
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