organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

1-(4-Nitro­phenyl)-2-({4-phenyl-5-[(p-tol­yl­oxy)meth­yl]-4H-1,2,4-triazol-3-yl}sulfan­yl)acetamide

CROSSMARK_Color_square_no_text.svg

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

Edited by J. Simpson, University of Otago, New Zealand (Received 28 September 2016; accepted 29 September 2016; online 7 October 2016)

In the crystal structure of the title compound, C24H21N5O4S, 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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

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[Godhani, D. R., Jogel, A. A., Sanghani, A. M. & Mehta, J. P. (2015). Indian J. Chem. Sect. B, 54, 556-564.]). Others such as Itraconazole, Fluconazole and Posaconazole have been used for the treatment of fungal infections (Godhani et al., 2015[Godhani, D. R., Jogel, A. A., Sanghani, A. M. & Mehta, J. P. (2015). Indian J. Chem. Sect. B, 54, 556-564.]). As part of our studies in this area, we report the synthesis and crystal structure of the title compound.

The mol­ecular conformation of the title compound (Fig. 1[link]) is partially stabilized by an intra­molecular C23—H23⋯O2 hydrogen bond (Table 1[link]). 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.

Table 1
Hydrogen-bond geometry (Å, °)

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 DA 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—H2ACg4iv 0.99 2.85 3.6592 (19) 140
C5—H5BCg1v 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.
[Figure 1]
Figure 1
The mol­ecular structure of the title mol­ecule, shown with 50% probability displacement ellipsoids. The intra­molecular hydrogen bond is shown as a dashed line.

In the crystal, pairs of mol­ecules are linked by pairwise N—H⋯N hydrogen bonds (Fig. 2[link]; Table 1[link]), forming inversion dimers with [R_{2}^{2}](16) ring motifs. C—H⋯O and C—H⋯π inter­actions (Table 1[link]) further connect these dimers, constructing an extended three-dimensional structure.

[Figure 2]
Figure 2
Packing of the title mol­ecule viewed down the b axis, with hydrogen bonds shown as dashed lines.

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 refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C24H21N5O4S
Mr 475.52
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 173
a, b, c (Å) 8.2241 (4), 12.2161 (7), 12.3952 (8)
α, β, γ (°) 115.507 (6), 93.532 (4), 96.914 (4)
V3) 1106.76 (12)
Z 2
Radiation type Cu Kα
μ (mm−1) 1.67
Crystal size (mm) 0.06 × 0.06 × 0.04
 
Data collection
Diffractometer Rigaku Oxford Diffraction four-circle
Absorption correction Multi-scan (CrysAlis PRO; Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.])
Tmin, Tmax 0.867, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 7218, 4208, 3685
Rint 0.031
(sin θ/λ)max−1) 0.615
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.102, 1.02
No. of reflections 4208
No. of parameters 308
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.27, −0.21
Computer programs: CrysAlis PRO (Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data


Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: 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).

1-(4-Nitrophenyl)-2-({4-phenyl-5-[(p-tolyloxy)methyl]-4H-1,2,4-triazol-3-yl}sulfanyl)acetamide top
Crystal data top
C24H21N5O4SZ = 2
Mr = 475.52F(000) = 496
Triclinic, P1Dx = 1.427 Mg m3
a = 8.2241 (4) ÅCu Kα radiation, λ = 1.54184 Å
b = 12.2161 (7) ÅCell parameters from 3208 reflections
c = 12.3952 (8) Åθ = 4.1–71.5°
α = 115.507 (6)°µ = 1.67 mm1
β = 93.532 (4)°T = 173 K
γ = 96.914 (4)°Prism, colourless
V = 1106.76 (12) Å30.06 × 0.06 × 0.04 mm
Data collection top
Rigaku Oxford Diffraction four-circle
diffractometer
4208 independent reflections
Radiation source: Enhance (Cu) X-ray Source3685 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 16.0416 pixels mm-1θmax = 71.4°, θmin = 4.0°
ω scansh = 98
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1413
Tmin = 0.867, Tmax = 1.000l = 1115
7218 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-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 reflectionsΔρmax = 0.27 e Å3
308 parametersΔρmin = 0.21 e Å3
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.85636 (5)0.52431 (4)0.73550 (4)0.02853 (13)
O10.97273 (15)0.31095 (11)0.56291 (10)0.0278 (3)
O20.45307 (13)0.80442 (10)1.06977 (10)0.0243 (2)
O31.43377 (17)0.21534 (12)0.47098 (13)0.0371 (3)
O41.30848 (18)0.22799 (12)0.30651 (11)0.0371 (3)
N11.14295 (17)0.27467 (12)0.69315 (12)0.0232 (3)
H11.18410.30650.76960.028*
N20.60984 (16)0.59879 (11)0.87254 (11)0.0193 (3)
N30.82466 (16)0.57455 (12)0.97176 (12)0.0228 (3)
N40.70552 (17)0.61560 (12)1.04921 (12)0.0226 (3)
N51.34846 (18)0.17518 (13)0.41631 (13)0.0268 (3)
C11.04125 (18)0.34015 (14)0.66351 (14)0.0210 (3)
C21.0260 (2)0.45989 (15)0.77194 (14)0.0256 (3)
H2A1.12980.51900.79330.031*
H2B1.00640.44370.84210.031*
C30.76396 (18)0.56551 (13)0.86744 (14)0.0199 (3)
C40.58071 (18)0.62961 (13)0.98868 (14)0.0197 (3)
C50.42806 (19)0.67541 (14)1.03736 (14)0.0216 (3)
H5A0.33070.63240.97560.026*
H5B0.40980.66121.10880.026*
C61.19059 (19)0.16297 (14)0.61755 (14)0.0210 (3)
C71.2798 (2)0.10810 (15)0.67497 (14)0.0238 (3)
H71.30480.14750.76030.029*
C81.3318 (2)0.00215 (15)0.60955 (15)0.0248 (3)
H81.39290.03900.64870.030*
C91.29292 (19)0.05829 (14)0.48512 (14)0.0234 (3)
C101.2067 (2)0.00546 (15)0.42604 (14)0.0254 (3)
H101.18280.04530.34070.030*
C111.1553 (2)0.10597 (15)0.49199 (14)0.0248 (3)
H111.09660.14330.45210.030*
C120.3168 (2)0.86318 (15)1.09212 (14)0.0224 (3)
C130.1555 (2)0.80569 (16)1.07641 (15)0.0258 (3)
H130.13090.71921.04880.031*
C140.0296 (2)0.87682 (17)1.10171 (16)0.0297 (4)
H140.08120.83721.08970.036*
C150.0612 (2)1.00335 (17)1.14384 (16)0.0308 (4)
C160.2244 (2)1.05886 (17)1.15901 (18)0.0351 (4)
H160.24921.14551.18770.042*
C170.3516 (2)0.98984 (16)1.13290 (17)0.0303 (4)
H170.46211.02911.14290.036*
C180.49849 (18)0.59151 (14)0.77434 (13)0.0192 (3)
C190.4528 (2)0.47990 (15)0.67390 (15)0.0247 (3)
H190.49430.40890.66930.030*
C200.3451 (2)0.47341 (18)0.57963 (15)0.0327 (4)
H200.31340.39760.50940.039*
C210.2835 (2)0.5773 (2)0.58765 (17)0.0382 (4)
H210.20900.57230.52330.046*
C220.3302 (2)0.68759 (19)0.68882 (18)0.0359 (4)
H220.28800.75840.69370.043*
C230.4384 (2)0.69645 (15)0.78381 (15)0.0262 (3)
H230.47060.77250.85370.031*
C240.0755 (3)1.0801 (2)1.1751 (2)0.0413 (5)
H24A0.18141.02811.13270.062*
H24B0.05411.14631.15060.062*
H24C0.07971.11571.26220.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0298 (2)0.0410 (2)0.0215 (2)0.02142 (17)0.00957 (15)0.01517 (18)
O10.0292 (6)0.0312 (6)0.0189 (6)0.0121 (5)0.0009 (4)0.0058 (5)
O20.0214 (5)0.0185 (5)0.0281 (6)0.0071 (4)0.0044 (4)0.0047 (5)
O30.0416 (7)0.0287 (7)0.0399 (7)0.0170 (5)0.0058 (6)0.0110 (6)
O40.0542 (8)0.0279 (6)0.0238 (7)0.0121 (6)0.0136 (6)0.0039 (5)
N10.0269 (7)0.0232 (7)0.0152 (6)0.0088 (5)0.0011 (5)0.0035 (5)
N20.0209 (6)0.0185 (6)0.0166 (6)0.0079 (5)0.0020 (5)0.0049 (5)
N30.0226 (6)0.0247 (7)0.0183 (6)0.0090 (5)0.0019 (5)0.0056 (5)
N40.0252 (7)0.0224 (6)0.0169 (6)0.0087 (5)0.0020 (5)0.0045 (5)
N50.0291 (7)0.0215 (7)0.0277 (7)0.0059 (5)0.0105 (6)0.0076 (6)
C10.0182 (7)0.0231 (8)0.0197 (7)0.0059 (6)0.0038 (5)0.0067 (6)
C20.0224 (8)0.0297 (8)0.0207 (8)0.0132 (6)0.0013 (6)0.0054 (7)
C30.0201 (7)0.0179 (7)0.0195 (7)0.0076 (5)0.0030 (5)0.0051 (6)
C40.0219 (7)0.0173 (7)0.0167 (7)0.0046 (5)0.0015 (5)0.0043 (6)
C50.0240 (8)0.0186 (7)0.0198 (7)0.0076 (6)0.0043 (6)0.0051 (6)
C60.0205 (7)0.0202 (7)0.0194 (7)0.0046 (5)0.0031 (5)0.0056 (6)
C70.0261 (8)0.0261 (8)0.0162 (7)0.0065 (6)0.0020 (6)0.0061 (6)
C80.0261 (8)0.0255 (8)0.0236 (8)0.0087 (6)0.0042 (6)0.0102 (7)
C90.0245 (8)0.0192 (7)0.0230 (8)0.0050 (6)0.0082 (6)0.0052 (6)
C100.0295 (8)0.0252 (8)0.0161 (7)0.0056 (6)0.0043 (6)0.0038 (6)
C110.0279 (8)0.0267 (8)0.0186 (8)0.0086 (6)0.0024 (6)0.0079 (6)
C120.0240 (8)0.0242 (8)0.0196 (7)0.0109 (6)0.0051 (6)0.0081 (6)
C130.0260 (8)0.0263 (8)0.0241 (8)0.0075 (6)0.0044 (6)0.0091 (7)
C140.0249 (8)0.0369 (9)0.0295 (9)0.0112 (7)0.0064 (6)0.0146 (8)
C150.0352 (9)0.0346 (9)0.0303 (9)0.0193 (7)0.0110 (7)0.0170 (8)
C160.0390 (10)0.0255 (9)0.0448 (11)0.0144 (7)0.0116 (8)0.0160 (8)
C170.0271 (8)0.0247 (8)0.0386 (10)0.0071 (6)0.0067 (7)0.0123 (7)
C180.0174 (7)0.0240 (7)0.0175 (7)0.0075 (5)0.0031 (5)0.0091 (6)
C190.0253 (8)0.0249 (8)0.0207 (8)0.0073 (6)0.0032 (6)0.0064 (6)
C200.0266 (9)0.0439 (10)0.0188 (8)0.0043 (7)0.0009 (6)0.0064 (7)
C210.0315 (9)0.0656 (13)0.0243 (9)0.0183 (9)0.0025 (7)0.0237 (9)
C220.0393 (10)0.0481 (11)0.0353 (10)0.0259 (8)0.0113 (8)0.0268 (9)
C230.0308 (8)0.0258 (8)0.0258 (8)0.0123 (6)0.0066 (6)0.0125 (7)
C240.0420 (11)0.0482 (12)0.0473 (12)0.0285 (9)0.0189 (9)0.0265 (10)
Geometric parameters (Å, º) top
S1—C21.8062 (16)C9—C101.381 (2)
S1—C31.7440 (15)C10—H100.9500
O1—C11.217 (2)C10—C111.387 (2)
O2—C51.4331 (19)C11—H110.9500
O2—C121.3816 (19)C12—C131.385 (2)
O3—N51.226 (2)C12—C171.390 (2)
O4—N51.231 (2)C13—H130.9500
N1—H10.8800C13—C141.395 (2)
N1—C11.360 (2)C14—H140.9500
N1—C61.402 (2)C14—C151.386 (3)
N2—C31.3739 (19)C15—C161.392 (3)
N2—C41.367 (2)C15—C241.513 (2)
N2—C181.4415 (19)C16—H160.9500
N3—N41.3973 (18)C16—C171.389 (2)
N3—C31.311 (2)C17—H170.9500
N4—C41.305 (2)C18—C191.381 (2)
N5—C91.460 (2)C18—C231.390 (2)
C1—C21.528 (2)C19—H190.9500
C2—H2A0.9900C19—C201.390 (2)
C2—H2B0.9900C20—H200.9500
C4—C51.492 (2)C20—C211.389 (3)
C5—H5A0.9900C21—H210.9500
C5—H5B0.9900C21—C221.377 (3)
C6—C71.400 (2)C22—H220.9500
C6—C111.398 (2)C22—C231.388 (3)
C7—H70.9500C23—H230.9500
C7—C81.377 (2)C24—H24A0.9800
C8—H80.9500C24—H24B0.9800
C8—C91.388 (2)C24—H24C0.9800
C3—S1—C299.82 (8)C9—C10—C11119.64 (15)
C12—O2—C5117.66 (12)C11—C10—H10120.2
C1—N1—H1115.8C6—C11—H11120.3
C1—N1—C6128.31 (14)C10—C11—C6119.48 (15)
C6—N1—H1115.8C10—C11—H11120.3
C3—N2—C18127.40 (13)O2—C12—C13125.17 (15)
C4—N2—C3104.43 (12)O2—C12—C17114.73 (15)
C4—N2—C18127.94 (13)C13—C12—C17120.10 (15)
C3—N3—N4106.31 (12)C12—C13—H13120.5
C4—N4—N3107.88 (12)C12—C13—C14118.91 (16)
O3—N5—O4123.30 (14)C14—C13—H13120.5
O3—N5—C9118.18 (14)C13—C14—H14118.9
O4—N5—C9118.52 (15)C15—C14—C13122.12 (16)
O1—C1—N1125.37 (14)C15—C14—H14118.9
O1—C1—C2122.69 (14)C14—C15—C16117.81 (16)
N1—C1—C2111.91 (13)C14—C15—C24121.68 (18)
S1—C2—H2A109.8C16—C15—C24120.49 (17)
S1—C2—H2B109.8C15—C16—H16119.4
C1—C2—S1109.43 (11)C17—C16—C15121.14 (17)
C1—C2—H2A109.8C17—C16—H16119.4
C1—C2—H2B109.8C12—C17—H17120.0
H2A—C2—H2B108.2C16—C17—C12119.90 (16)
N2—C3—S1120.49 (11)C16—C17—H17120.0
N3—C3—S1128.51 (12)C19—C18—N2119.01 (14)
N3—C3—N2110.95 (13)C19—C18—C23121.77 (15)
N2—C4—C5123.61 (14)C23—C18—N2119.21 (14)
N4—C4—N2110.42 (13)C18—C19—H19120.6
N4—C4—C5125.95 (14)C18—C19—C20118.73 (16)
O2—C5—C4106.51 (12)C20—C19—H19120.6
O2—C5—H5A110.4C19—C20—H20119.9
O2—C5—H5B110.4C21—C20—C19120.28 (17)
C4—C5—H5A110.4C21—C20—H20119.9
C4—C5—H5B110.4C20—C21—H21120.0
H5A—C5—H5B108.6C22—C21—C20120.01 (16)
C7—C6—N1115.99 (14)C22—C21—H21120.0
C11—C6—N1124.33 (15)C21—C22—H22119.6
C11—C6—C7119.68 (15)C21—C22—C23120.73 (17)
C6—C7—H7119.6C23—C22—H22119.6
C8—C7—C6120.89 (15)C18—C23—H23120.8
C8—C7—H7119.6C22—C23—C18118.46 (16)
C7—C8—H8120.8C22—C23—H23120.8
C7—C8—C9118.50 (15)C15—C24—H24A109.5
C9—C8—H8120.8C15—C24—H24B109.5
C8—C9—N5118.20 (15)C15—C24—H24C109.5
C10—C9—N5119.99 (15)H24A—C24—H24B109.5
C10—C9—C8121.80 (15)H24A—C24—H24C109.5
C9—C10—H10120.2H24B—C24—H24C109.5
O1—C1—C2—S114.8 (2)C4—N2—C18—C2361.2 (2)
O2—C12—C13—C14179.47 (15)C5—O2—C12—C135.5 (2)
O2—C12—C17—C16179.65 (16)C5—O2—C12—C17174.82 (14)
O3—N5—C9—C83.5 (2)C6—N1—C1—O10.1 (3)
O3—N5—C9—C10175.33 (15)C6—N1—C1—C2177.91 (15)
O4—N5—C9—C8176.98 (15)C6—C7—C8—C90.4 (2)
O4—N5—C9—C104.2 (2)C7—C6—C11—C101.1 (2)
N1—C1—C2—S1167.16 (11)C7—C8—C9—N5179.99 (15)
N1—C6—C7—C8179.55 (15)C7—C8—C9—C101.2 (2)
N1—C6—C11—C10179.18 (15)C8—C9—C10—C110.8 (3)
N2—C4—C5—O282.51 (17)C9—C10—C11—C60.4 (2)
N2—C18—C19—C20179.83 (14)C11—C6—C7—C80.7 (2)
N2—C18—C23—C22179.48 (15)C12—O2—C5—C4165.95 (13)
N3—N4—C4—N20.43 (17)C12—C13—C14—C151.0 (3)
N3—N4—C4—C5178.18 (14)C13—C12—C17—C160.6 (3)
N4—N3—C3—S1177.46 (12)C13—C14—C15—C160.9 (3)
N4—N3—C3—N20.00 (17)C13—C14—C15—C24177.84 (17)
N4—C4—C5—O295.93 (18)C14—C15—C16—C170.0 (3)
N5—C9—C10—C11179.59 (14)C15—C16—C17—C120.7 (3)
C1—N1—C6—C7172.03 (15)C17—C12—C13—C140.2 (2)
C1—N1—C6—C118.3 (3)C18—N2—C3—S17.8 (2)
C2—S1—C3—N2168.01 (12)C18—N2—C3—N3174.54 (14)
C2—S1—C3—N314.74 (16)C18—N2—C4—N4174.33 (14)
C3—S1—C2—C1135.78 (12)C18—N2—C4—C57.0 (2)
C3—N2—C4—N40.42 (17)C18—C19—C20—C210.8 (3)
C3—N2—C4—C5178.23 (14)C19—C18—C23—C220.3 (2)
C3—N2—C18—C1955.5 (2)C19—C20—C21—C220.6 (3)
C3—N2—C18—C23125.25 (17)C20—C21—C22—C230.2 (3)
C3—N3—N4—C40.26 (17)C21—C22—C23—C180.1 (3)
C4—N2—C3—S1177.45 (11)C23—C18—C19—C200.6 (2)
C4—N2—C3—N30.25 (17)C24—C15—C16—C17178.74 (18)
C4—N2—C18—C19118.08 (17)
Hydrogen-bond geometry (Å, º) top
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···AD—HH···AD···AD—H···A
N1—H1···N4i0.882.122.9949 (19)177
C5—H5B···O4ii0.992.493.2838 (19)137
C7—H7···O2i0.952.623.413 (2)141
C19—H19···O3iii0.952.433.236 (2)143
C23—H23···O20.952.553.194 (2)125
C2—H2A···Cg4iv0.992.853.6592 (19)140
C5—H5B···Cg1v0.992.923.433 (2)113
C10—H10···Cg3vi0.952.673.5536 (18)156
C14—H14···Cg1vii0.952.983.781 (2)143
Symmetry codes: (i) x+2, y+1, z+2; (ii) x1, 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, y1, z1; (vii) x1, y, z.
 

Acknowledgements

JPJ would like to acknowledge the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X ray diffractometer.

References

First citationAgilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.  Google Scholar
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationGodhani, D. R., Jogel, A. A., Sanghani, A. M. & Mehta, J. P. (2015). Indian J. Chem. Sect. B, 54, 556–564.  Google Scholar
First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar

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