2-{[5-(4-Chloro­phen­oxy­meth­yl)-4-phenyl-4H-1,2,4-triazol-3-yl]sulfan­yl}-N-(4-nitro­phen­yl)acetamide

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Ahmed, G.A.-W.; Bakhite, E.A.; Albayati, M.R.

doi:10.1107/S2414314616004521

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 3| March 2016| x160452

doi:10.1107/S2414314616004521

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2-{[5-(4-Chlorophenoxymethyl)-4-phenyl-4H-1,2,4-triazol-3-yl]sulfanyl}-N-(4-nitrophenyl)acetamide

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Gamal A.-W. Ahmed,^e Etify A. Bakhite ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eChemistry Department, Faculty of Science, Assiut University, 71516 Assiut, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by H. Ishida, Okayama University, Japan (Received 11 March 2016; accepted 16 March 2016; online 18 March 2016)

The title molecule, C₂₃H₁₈ClN₅O₄S, is in an `extended' conformation. The central triazole ring makes dihedral angles of 58.14 (6), 86.29 (6) and 41.99 (6)°, respectively, with the adjacent phenyl, chlorophenyl and nitrophenyl rings. In the crystal, molecules are linked via a pair of N—H⋯N hydrogen bonds with an R₂²(16) ring motif, forming an inversion dimer. The dimers are connected by C—H⋯O hydrogen bonds into a tape structure along [011]. C—H⋯π interactions between the tapes are also observed.

Keywords: crystal structure; phenyltriazole; thiotriazole.

CCDC reference: 1468941

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Chemical scheme

Structure description

1,2,4-Triazole and its derivatives represent one of the most biologically active class of heterocyclic compounds. There are a large number of drugs containing a 1,2,4-triazole nucleus in their structures. These include 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 infection diseases (Godhani et al., 2015). In view of the above facts, we report in this context the synthesis and crystal structure of the title compound (Fig. 1).

Figure 1
The molecular structure of the title compound, showing the atom-labeling scheme and 50% probability ellipsoids.

In the crystal, molecules form a tape structure through N—H⋯N and C—H⋯O hydrogen bonds (Table 1 and Fig. 2). C—H⋯π interactions between the tapes contribute to the stabilization of the molecular packing.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the 1,2,4-triazole (N1/N2/C9/N3/C8), benzene (C1–C6) and phenyl (C10–C15) rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N1ⁱ	0.91	2.08	2.9934 (17)	176
C15—H15⋯O4ⁱⁱ	0.95	2.44	3.2324 (19)	140
C5—H5⋯Cg1ⁱⁱⁱ	0.95	2.97	3.757 (2)	141
C16—H16A⋯Cg3^iv	0.99	2.82	3.6284 (18)	139
C22—H22⋯Cg2^v	0.95	2.69	3.5883 (16)	158
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+2, -y, -z+1; (iii) x-1, y, z; (iv) x+1, y, z; (v) x+1, y-1, z-1.

Figure 2
A packing diagram of the title compound, showing the tapes formed by N—H⋯N and C—H⋯O hydrogen bonds (blue and black dotted lines, respectively).

Synthesis and crystallization

A suspension of 5-(4-chlorphenoxy)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 until dryness. The solid residue was crystallized from ethanol to give the title compound. Yield: 93%; m.p. 207°C. IR (cm⁻¹): 3300 (NH), 1660 (C=O). ¹H NMR (CDCl₃, p.p.m.): δ 9.2 (s, 1H, NH), 6.7–8.0 (m, 13H, ArH), 4.9 (s, 2H, OCH₂), 4.0 (s, 2H,SCH₂).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₃H₁₈ClN₅O₄S
M_r	495.93
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	150
a, b, c (Å)	8.1828 (2), 12.1541 (3), 12.3654 (3)
α, β, γ (°)	114.474 (1), 93.681 (1), 96.949 (1)
V (Å³)	1102.14 (5)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	2.79
Crystal size (mm)	0.21 × 0.18 × 0.03

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.80, 0.93
No. of measured, independent and observed [I > 2σ(I)] reflections	8470, 4084, 3709
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.089, 1.04
No. of reflections	4084
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.35
Computer programs: APEX3 (Bruker, 2016), SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015b ), SHELXL2014 (Sheldrick, 2015a ), DIAMOND (Brandenburg & Putz, 2012 ).

Structural data

CCDC reference: 1468941

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616004521/is4005sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616004521/is4005Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616004521/is4005Isup3.cml

checkCIF report

Experimental top

Structure description top

1,2,4-Triazole and its derivatives represent one of the most biologically active class of heterocyclic compounds. There are a large number of drugs containing a 1,2,4-triazole nucleus in their structures. These include 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 infection diseases (Godhani et al., 2015). In view of the above facts, we report in this context the synthesis and crystal structure of the title compound (Fig. 1).

In the crystal, molecules form a tape structure through N—H···N and C—H···O hydrogen bonds (Table 1 and Fig. 2). C—H···π interactions between the tapes contribute to the stabilization of the molecular packing.

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015a); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015a).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme and 50% probability ellipsoids.
	Fig. 2. A packing diagram of the title compound, showing the tapes formed by N—H···N and C—H···O hydrogen bonds (blue and black dotted lines, respectively).

2-{[5-(4-Chlorophenoxymethyl)-4-phenyl-4H-1,2,4-triazol-3-yl]sulfanyl}-N-(4-nitrophenyl)acetamide top

Crystal data top

C₂₃H₁₈ClN₅O₄S	Z = 2
M_r = 495.93	F(000) = 512
Triclinic, P1	D_x = 1.494 Mg m⁻³
a = 8.1828 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 12.1541 (3) Å	Cell parameters from 6886 reflections
c = 12.3654 (3) Å	θ = 4.0–72.3°
α = 114.474 (1)°	µ = 2.79 mm⁻¹
β = 93.681 (1)°	T = 150 K
γ = 96.949 (1)°	Plate, colourless
V = 1102.14 (5) Å³	0.21 × 0.18 × 0.03 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	4084 independent reflections
Radiation source: INCOATEC IµS micro–focus source	3709 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.023
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.3°, θ_min = 4.0°
ω scans	h = −9→10
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −14→13
T_min = 0.80, T_max = 0.93	l = −15→15
8470 measured reflections

Refinement top

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)] = 0.034	Hydrogen site location: mixed
wR(F²) = 0.089	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.048P)² + 0.4011P] where P = (F_o² + 2F_c²)/3
4084 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₃H₁₈ClN₅O₄S	γ = 96.949 (1)°
M_r = 495.93	V = 1102.14 (5) Å³
Triclinic, P1	Z = 2
a = 8.1828 (2) Å	Cu Kα radiation
b = 12.1541 (3) Å	µ = 2.79 mm⁻¹
c = 12.3654 (3) Å	T = 150 K
α = 114.474 (1)°	0.21 × 0.18 × 0.03 mm
β = 93.681 (1)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	4084 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2016)	3709 reflections with I > 2σ(I)
T_min = 0.80, T_max = 0.93	R_int = 0.023
8470 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.04	Δρ_max = 0.17 e Å⁻³
4084 reflections	Δρ_min = −0.35 e Å⁻³
307 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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) top

	x	y	z	U_iso*/U_eq
Cl1	−0.09452 (6)	1.08937 (5)	1.17426 (5)	0.04449 (14)
S1	0.85499 (5)	0.52367 (4)	0.73580 (3)	0.02790 (12)
O1	0.45177 (13)	0.80389 (9)	1.06669 (9)	0.0230 (2)
O2	0.96933 (13)	0.31268 (10)	0.56493 (9)	0.0260 (2)
O3	1.30812 (16)	−0.22278 (10)	0.30629 (10)	0.0333 (3)
O4	1.43386 (15)	−0.21478 (10)	0.46972 (11)	0.0335 (3)
N1	0.70644 (15)	0.61703 (11)	1.04995 (11)	0.0215 (3)
N2	0.82617 (15)	0.57622 (11)	0.97273 (11)	0.0219 (3)
N3	0.60856 (14)	0.59829 (11)	0.87198 (10)	0.0184 (2)
N4	1.14142 (15)	0.27311 (11)	0.69377 (11)	0.0215 (3)
H4	1.1865	0.3031	0.7717	0.026*
N5	1.34798 (16)	−0.17258 (12)	0.41598 (12)	0.0253 (3)
C1	0.31563 (19)	0.86299 (14)	1.08991 (13)	0.0218 (3)
C2	0.3516 (2)	0.98921 (15)	1.13020 (15)	0.0289 (3)
H2	0.4630	1.0278	1.1399	0.035*
C3	0.2256 (2)	1.05892 (16)	1.15629 (16)	0.0335 (4)
H3	0.2500	1.1454	1.1848	0.040*
C4	0.0633 (2)	1.00125 (16)	1.14047 (15)	0.0300 (4)
C5	0.0266 (2)	0.87596 (16)	1.09983 (14)	0.0281 (3)
H5	−0.0854	0.8376	1.0887	0.034*
C6	0.15317 (19)	0.80536 (14)	1.07504 (13)	0.0241 (3)
H6	0.1287	0.7191	1.0484	0.029*
C7	0.42651 (18)	0.67518 (13)	1.03645 (13)	0.0208 (3)
H7A	0.3285	0.6324	0.9753	0.025*
H7B	0.4086	0.6607	1.1083	0.025*
C8	0.57961 (18)	0.63017 (12)	0.98852 (12)	0.0189 (3)
C9	0.76419 (17)	0.56569 (13)	0.86746 (13)	0.0197 (3)
C10	0.49571 (17)	0.58946 (13)	0.77336 (12)	0.0188 (3)
C11	0.4338 (2)	0.69254 (14)	0.77869 (14)	0.0255 (3)
H11	0.4648	0.7689	0.8467	0.031*
C12	0.3251 (2)	0.68181 (18)	0.68222 (15)	0.0344 (4)
H12	0.2811	0.7514	0.6844	0.041*
C13	0.2809 (2)	0.57079 (19)	0.58354 (15)	0.0354 (4)
H13	0.2066	0.5643	0.5181	0.043*
C14	0.3442 (2)	0.46872 (17)	0.57942 (14)	0.0299 (4)
H14	0.3138	0.3926	0.5109	0.036*
C15	0.45185 (19)	0.47706 (14)	0.67500 (13)	0.0230 (3)
H15	0.4946	0.4071	0.6730	0.028*
C16	1.02531 (19)	0.45839 (14)	0.77244 (13)	0.0244 (3)
H16A	1.1299	0.5171	0.7933	0.029*
H16B	1.0057	0.4410	0.8424	0.029*
C17	1.03937 (17)	0.34014 (13)	0.66470 (13)	0.0203 (3)
C18	1.18868 (18)	0.16229 (13)	0.61799 (13)	0.0202 (3)
C19	1.27723 (18)	0.10494 (14)	0.67439 (13)	0.0227 (3)
H19	1.3019	0.1421	0.7592	0.027*
C20	1.32914 (19)	−0.00431 (14)	0.60902 (13)	0.0237 (3)
H20	1.3893	−0.0429	0.6477	0.028*
C21	1.29176 (18)	−0.05704 (13)	0.48524 (13)	0.0222 (3)
C22	1.20524 (19)	−0.00199 (14)	0.42706 (13)	0.0232 (3)
H22	1.1816	−0.0396	0.3422	0.028*
C23	1.15320 (19)	0.10814 (14)	0.49296 (13)	0.0231 (3)
H23	1.0939	0.1466	0.4537	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0467 (3)	0.0525 (3)	0.0530 (3)	0.0368 (2)	0.0247 (2)	0.0304 (2)
S1	0.0279 (2)	0.0415 (2)	0.02153 (19)	0.02142 (17)	0.00882 (15)	0.01553 (16)
O1	0.0191 (5)	0.0182 (5)	0.0288 (5)	0.0078 (4)	0.0043 (4)	0.0056 (4)
O2	0.0258 (5)	0.0308 (6)	0.0187 (5)	0.0112 (5)	−0.0004 (4)	0.0067 (4)
O3	0.0445 (7)	0.0286 (6)	0.0223 (6)	0.0105 (5)	0.0096 (5)	0.0045 (5)
O4	0.0361 (6)	0.0279 (6)	0.0365 (6)	0.0152 (5)	0.0051 (5)	0.0111 (5)
N1	0.0220 (6)	0.0234 (6)	0.0170 (6)	0.0089 (5)	0.0021 (5)	0.0053 (5)
N2	0.0206 (6)	0.0253 (6)	0.0186 (6)	0.0098 (5)	0.0030 (5)	0.0063 (5)
N3	0.0177 (6)	0.0205 (6)	0.0169 (6)	0.0092 (5)	0.0023 (5)	0.0061 (4)
N4	0.0226 (6)	0.0235 (6)	0.0160 (6)	0.0089 (5)	0.0011 (5)	0.0049 (5)
N5	0.0260 (7)	0.0227 (6)	0.0256 (7)	0.0058 (5)	0.0083 (5)	0.0076 (5)
C1	0.0220 (7)	0.0243 (7)	0.0203 (7)	0.0107 (6)	0.0047 (6)	0.0085 (6)
C2	0.0275 (8)	0.0237 (8)	0.0349 (8)	0.0074 (7)	0.0060 (7)	0.0108 (6)
C3	0.0397 (9)	0.0246 (8)	0.0398 (9)	0.0144 (7)	0.0108 (8)	0.0138 (7)
C4	0.0320 (9)	0.0357 (9)	0.0312 (8)	0.0214 (7)	0.0122 (7)	0.0175 (7)
C5	0.0231 (7)	0.0354 (9)	0.0291 (8)	0.0102 (7)	0.0067 (6)	0.0151 (7)
C6	0.0238 (7)	0.0254 (7)	0.0235 (7)	0.0086 (6)	0.0055 (6)	0.0091 (6)
C7	0.0206 (7)	0.0190 (7)	0.0208 (7)	0.0064 (6)	0.0038 (6)	0.0055 (5)
C8	0.0205 (7)	0.0171 (6)	0.0173 (6)	0.0058 (6)	0.0025 (5)	0.0048 (5)
C9	0.0177 (7)	0.0201 (7)	0.0202 (7)	0.0077 (6)	0.0023 (5)	0.0064 (5)
C10	0.0164 (6)	0.0244 (7)	0.0174 (7)	0.0074 (6)	0.0021 (5)	0.0095 (5)
C11	0.0296 (8)	0.0262 (8)	0.0250 (7)	0.0129 (6)	0.0065 (6)	0.0125 (6)
C12	0.0390 (9)	0.0474 (10)	0.0313 (9)	0.0273 (8)	0.0115 (8)	0.0246 (8)
C13	0.0283 (8)	0.0634 (12)	0.0216 (8)	0.0206 (8)	0.0050 (7)	0.0211 (8)
C14	0.0237 (7)	0.0418 (9)	0.0187 (7)	0.0062 (7)	0.0020 (6)	0.0073 (6)
C15	0.0220 (7)	0.0252 (7)	0.0205 (7)	0.0077 (6)	0.0037 (6)	0.0074 (6)
C16	0.0206 (7)	0.0287 (8)	0.0201 (7)	0.0113 (6)	0.0014 (6)	0.0049 (6)
C17	0.0164 (6)	0.0237 (7)	0.0198 (7)	0.0055 (6)	0.0037 (5)	0.0076 (6)
C18	0.0174 (6)	0.0219 (7)	0.0199 (7)	0.0059 (6)	0.0037 (5)	0.0066 (6)
C19	0.0228 (7)	0.0260 (7)	0.0176 (7)	0.0063 (6)	0.0020 (6)	0.0072 (6)
C20	0.0234 (7)	0.0258 (7)	0.0237 (7)	0.0082 (6)	0.0029 (6)	0.0113 (6)
C21	0.0213 (7)	0.0210 (7)	0.0222 (7)	0.0058 (6)	0.0068 (6)	0.0061 (6)
C22	0.0243 (7)	0.0254 (7)	0.0172 (7)	0.0048 (6)	0.0028 (6)	0.0062 (6)
C23	0.0241 (7)	0.0261 (8)	0.0189 (7)	0.0081 (6)	0.0019 (6)	0.0084 (6)

Geometric parameters (Å, º) top

Cl1—C4	1.7387 (16)	C7—C8	1.487 (2)
S1—C9	1.7383 (15)	C7—H7A	0.9900
S1—C16	1.8061 (15)	C7—H7B	0.9900
O1—C1	1.3796 (18)	C10—C11	1.386 (2)
O1—C7	1.4343 (18)	C10—C15	1.387 (2)
O2—C17	1.2181 (18)	C11—C12	1.392 (2)
O3—N5	1.2360 (17)	C11—H11	0.9500
O4—N5	1.2281 (18)	C12—C13	1.379 (3)
N1—C8	1.3111 (19)	C12—H12	0.9500
N1—N2	1.4010 (18)	C13—C14	1.384 (3)
N2—C9	1.3151 (18)	C13—H13	0.9500
N3—C8	1.3734 (19)	C14—C15	1.389 (2)
N3—C9	1.3765 (18)	C14—H14	0.9500
N3—C10	1.4403 (17)	C15—H15	0.9500
N4—C17	1.3634 (19)	C16—C17	1.525 (2)
N4—C18	1.4031 (18)	C16—H16A	0.9900
N4—H4	0.9098	C16—H16B	0.9900
N5—C21	1.4586 (19)	C18—C19	1.399 (2)
C1—C2	1.388 (2)	C18—C23	1.400 (2)
C1—C6	1.389 (2)	C19—C20	1.374 (2)
C2—C3	1.383 (2)	C19—H19	0.9500
C2—H2	0.9500	C20—C21	1.388 (2)
C3—C4	1.386 (3)	C20—H20	0.9500
C3—H3	0.9500	C21—C22	1.384 (2)
C4—C5	1.377 (2)	C22—C23	1.384 (2)
C5—C6	1.393 (2)	C22—H22	0.9500
C5—H5	0.9500	C23—H23	0.9500
C6—H6	0.9500

C9—S1—C16	100.00 (7)	C11—C10—N3	119.63 (13)
C1—O1—C7	117.68 (12)	C15—C10—N3	118.71 (13)
C8—N1—N2	107.77 (12)	C10—C11—C12	118.59 (15)
C9—N2—N1	106.62 (11)	C10—C11—H11	120.7
C8—N3—C9	104.71 (11)	C12—C11—H11	120.7
C8—N3—C10	127.83 (12)	C13—C12—C11	120.44 (15)
C9—N3—C10	127.22 (12)	C13—C12—H12	119.8
C17—N4—C18	128.21 (12)	C11—C12—H12	119.8
C17—N4—H4	117.2	C12—C13—C14	120.28 (15)
C18—N4—H4	114.6	C12—C13—H13	119.9
O4—N5—O3	123.20 (13)	C14—C13—H13	119.9
O4—N5—C21	118.18 (13)	C13—C14—C15	120.28 (15)
O3—N5—C21	118.62 (13)	C13—C14—H14	119.9
O1—C1—C2	114.63 (14)	C15—C14—H14	119.9
O1—C1—C6	124.88 (14)	C10—C15—C14	118.74 (15)
C2—C1—C6	120.50 (14)	C10—C15—H15	120.6
C3—C2—C1	120.19 (16)	C14—C15—H15	120.6
C3—C2—H2	119.9	C17—C16—S1	109.03 (10)
C1—C2—H2	119.9	C17—C16—H16A	109.9
C2—C3—C4	119.29 (16)	S1—C16—H16A	109.9
C2—C3—H3	120.4	C17—C16—H16B	109.9
C4—C3—H3	120.4	S1—C16—H16B	109.9
C5—C4—C3	120.85 (15)	H16A—C16—H16B	108.3
C5—C4—Cl1	120.03 (14)	O2—C17—N4	125.33 (13)
C3—C4—Cl1	119.12 (13)	O2—C17—C16	122.69 (13)
C4—C5—C6	120.16 (15)	N4—C17—C16	111.96 (12)
C4—C5—H5	119.9	C19—C18—C23	119.61 (13)
C6—C5—H5	119.9	C19—C18—N4	116.02 (13)
C1—C6—C5	119.00 (15)	C23—C18—N4	124.37 (13)
C1—C6—H6	120.5	C20—C19—C18	121.02 (13)
C5—C6—H6	120.5	C20—C19—H19	119.5
O1—C7—C8	106.20 (12)	C18—C19—H19	119.5
O1—C7—H7A	110.5	C19—C20—C21	118.54 (14)
C8—C7—H7A	110.5	C19—C20—H20	120.7
O1—C7—H7B	110.5	C21—C20—H20	120.7
C8—C7—H7B	110.5	C22—C21—C20	121.67 (14)
H7A—C7—H7B	108.7	C22—C21—N5	119.88 (13)
N1—C8—N3	110.23 (13)	C20—C21—N5	118.45 (13)
N1—C8—C7	125.83 (13)	C21—C22—C23	119.76 (14)
N3—C8—C7	123.93 (12)	C21—C22—H22	120.1
N2—C9—N3	110.67 (13)	C23—C22—H22	120.1
N2—C9—S1	128.89 (11)	C22—C23—C18	119.40 (13)
N3—C9—S1	120.39 (10)	C22—C23—H23	120.3
C11—C10—C15	121.66 (13)	C18—C23—H23	120.3

C8—N1—N2—C9	−0.55 (16)	C8—N3—C10—C15	−118.65 (16)
C7—O1—C1—C2	173.83 (13)	C9—N3—C10—C15	54.9 (2)
C7—O1—C1—C6	−6.6 (2)	C15—C10—C11—C12	−0.1 (2)
O1—C1—C2—C3	179.81 (15)	N3—C10—C11—C12	179.91 (14)
C6—C1—C2—C3	0.2 (2)	C10—C11—C12—C13	−0.2 (3)
C1—C2—C3—C4	−0.7 (3)	C11—C12—C13—C14	0.0 (3)
C2—C3—C4—C5	0.3 (3)	C12—C13—C14—C15	0.5 (3)
C2—C3—C4—Cl1	179.61 (13)	C11—C10—C15—C14	0.6 (2)
C3—C4—C5—C6	0.6 (3)	N3—C10—C15—C14	−179.44 (13)
Cl1—C4—C5—C6	−178.67 (12)	C13—C14—C15—C10	−0.7 (2)
O1—C1—C6—C5	−178.85 (14)	C9—S1—C16—C17	136.78 (11)
C2—C1—C6—C5	0.7 (2)	C18—N4—C17—O2	0.8 (3)
C4—C5—C6—C1	−1.1 (2)	C18—N4—C17—C16	−177.53 (14)
C1—O1—C7—C8	166.87 (12)	S1—C16—C17—O2	14.43 (19)
N2—N1—C8—N3	0.69 (16)	S1—C16—C17—N4	−167.17 (11)
N2—N1—C8—C7	−178.20 (13)	C17—N4—C18—C19	−171.74 (14)
C9—N3—C8—N1	−0.55 (16)	C17—N4—C18—C23	8.4 (2)
C10—N3—C8—N1	174.12 (13)	C23—C18—C19—C20	−0.4 (2)
C9—N3—C8—C7	178.37 (13)	N4—C18—C19—C20	179.69 (14)
C10—N3—C8—C7	−7.0 (2)	C18—C19—C20—C21	0.0 (2)
O1—C7—C8—N1	95.45 (17)	C19—C20—C21—C22	0.4 (2)
O1—C7—C8—N3	−83.30 (16)	C19—C20—C21—N5	179.58 (14)
N1—N2—C9—N3	0.21 (16)	O4—N5—C21—C22	175.23 (14)
N1—N2—C9—S1	177.76 (11)	O3—N5—C21—C22	−4.3 (2)
C8—N3—C9—N2	0.19 (16)	O4—N5—C21—C20	−3.9 (2)
C10—N3—C9—N2	−174.52 (13)	O3—N5—C21—C20	176.57 (14)
C8—N3—C9—S1	−177.60 (10)	C20—C21—C22—C23	−0.3 (2)
C10—N3—C9—S1	7.7 (2)	N5—C21—C22—C23	−179.48 (14)
C16—S1—C9—N2	15.55 (16)	C21—C22—C23—C18	−0.1 (2)
C16—S1—C9—N3	−167.10 (12)	C19—C18—C23—C22	0.5 (2)
C8—N3—C10—C11	61.4 (2)	N4—C18—C23—C22	−179.62 (14)
C9—N3—C10—C11	−125.12 (16)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the 1,2,4-triazole (N1/N2/C9/N3/C8), benzene (C1–C6) and phenyl (C10–C15) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N1ⁱ	0.91	2.08	2.9934 (17)	176
C15—H15···O4ⁱⁱ	0.95	2.44	3.2324 (19)	140
C5—H5···Cg1ⁱⁱⁱ	0.95	2.97	3.757 (2)	141
C16—H16A···Cg3^iv	0.99	2.82	3.6284 (18)	139
C22—H22···Cg2^v	0.95	2.69	3.5883 (16)	158

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y, −z+1; (iii) x−1, y, z; (iv) x+1, y, z; (v) x+1, y−1, z−1.

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the 1,2,4-triazole (N1/N2/C9/N3/C8), benzene (C1–C6) and phenyl (C10–C15) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N1ⁱ	0.91	2.08	2.9934 (17)	176
C15—H15···O4ⁱⁱ	0.95	2.44	3.2324 (19)	140
C5—H5···Cg1ⁱⁱⁱ	0.95	2.97	3.757 (2)	141
C16—H16A···Cg3^iv	0.99	2.82	3.6284 (18)	139
C22—H22···Cg2^v	0.95	2.69	3.5883 (16)	158

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y, −z+1; (iii) x−1, y, z; (iv) x+1, y, z; (v) x+1, y−1, z−1.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈ClN₅O₄S
M_r	495.93
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	8.1828 (2), 12.1541 (3), 12.3654 (3)
α, β, γ (°)	114.474 (1), 93.681 (1), 96.949 (1)
V (Å³)	1102.14 (5)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.79
Crystal size (mm)	0.21 × 0.18 × 0.03

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016)
T_min, T_max	0.80, 0.93
No. of measured, independent and observed [I > 2σ(I)] reflections	8470, 4084, 3709
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.089, 1.04
No. of reflections	4084
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.35

Computer programs: APEX3 (Bruker, 2016), SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015b), SHELXL2014 (Sheldrick, 2015a), DIAMOND (Brandenburg & Putz, 2012).

Acknowledgements

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, WI. Google Scholar
Godhani, D. R., Jogel, A. A., Sanghani, A. M. & Mehta, J. P. (2015). Indian J. Chem. Section B, 54, 556–564. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

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ISSN: 2414-3146

Volume 1| Part 3| March 2016| x160452

doi:10.1107/S2414314616004521

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

2-{[5-(4-Chloro­phen­­oxy­meth­yl)-4-phenyl-4H-1,2,4-triazol-3-yl]sulfan­yl}-N-(4-nitro­phen­yl)acetamide

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

2-{[5-(4-Chlorophenoxymethyl)-4-phenyl-4H-1,2,4-triazol-3-yl]sulfanyl}-N-(4-nitrophenyl)acetamide