3-[(4-Phen-oxy-phen-yl)sulfan-yl]-5-phenyl-1H-1,2,4-triazole.

The title compound, C20H15N3OS, is V-shaped. In the 4-phen-oxy-phenyl group, the two rings are inclined to one another by 74.52 (13)°. These rings are inclined to the triazole ring by 72.20 (15) and 72.30 (15)°, respectively. The phenyl ring is inclined to the triazole ring by 10.85 (12)°. In the crystal, mol-ecules are linked via N-H⋯N hydrogen bonds, forming chains propagating along [010]. These chains are linked via pairs of C-H⋯S hydrogen bonds, forming sheets lying parallel to the ac plane.

Related literature

For the synthesis, properties and various biological activities of functionalizated 1,2,4-triazole derivatives, see: Holla et al. (2002 ▶, 2003 ▶); Walczak et al. (2004 ▶); Zitouni et al. (2005 ▶); Prasad et al. (2009 ▶); Wael et al. (2012 ▶); Almasirad et al. (2004 ▶); Amir & Shikha (2004 ▶); Kane et al. (1988 ▶); Akhtar et al. (2010 ▶). For the crystal structures of related N-free triazole derivatives, see for example: Qadeer et al. (2007 ▶); and for N-subsituted derivatives, see for example: Zhao et al. (2010 ▶); Wu et al. (2009 ▶). Working with sulfur-containing heterocycles may provide unexpected results and the title compound was obtained within an unprecedented series of results, see: Ben Othman et al. (2014 ▶).

Experimental

Crystal data

C20H15N3OS

M = 345.41

Monoclinic,

a = 16.6112 (12) Å

b = 5.8445 (5) Å

c = 17.5415 (10) Å

β = 93.131 (5)°

V = 1700.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 293 K

0.35 × 0.25 × 0.12 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.932, T max = 0.976

44120 measured reflections

3099 independent reflections

2333 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.152

S = 1.02

3099 reflections

207 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.30 e Å−3

Data collection: COLLECT (Bruker–Nonius, 1998) ▶; cell refinement: DIRAX/LSQ (Duisenberg, 1992 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814008204/su2718sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008204/su2718Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008204/su2718Isup3.cml

CCDC reference: 991904

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H15N3OS	Z = 4
Mr = 345.41	F(000) = 720
Monoclinic, P21/n	Dx = 1.349 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 16.6112 (12) Å	µ = 0.20 mm−1
b = 5.8445 (5) Å	T = 293 K
c = 17.5415 (10) Å	Block, colourless
β = 93.131 (5)°	0.35 × 0.25 × 0.12 mm
V = 1700.5 (2) Å3

Bruker–Nonius KappaCCD diffractometer	3099 independent reflections
Radiation source: sealed X-ray tube	2333 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
profile data from φ scans and ω scans	θmax = 25.4°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
Tmin = 0.932, Tmax = 0.976	k = −7→6
44120 measured reflections	l = −21→21

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)] = 0.052	Hydrogen site location: mixed
wR(F2) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0707P)2 + 1.0533P] where P = (Fo2 + 2Fc2)/3
3099 reflections	(Δ/σ)max = 0.001
207 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. Spectroscopic data for the title compound: IR (ATR diamond): ν (cm-1) = 3082, 2927, 2864, 1581, 1482, 1324, 1242, 1006, 869, 786, 601, 725, 688; 1H NMR (400 MHz, CDCl3) δ (p.p.m.) = 12.92 (br. s, 1H), 7.90 (d, J = 6.9 Hz, 2H), 7.47 (d, J = 8.4 Hz, 2H), 7.43–7.28 (m, 5H), 7.15 (t, J = 7.3 Hz, 1H), 6.96 (d, J = 7.8 Hz, 2H), 6.84 (d, J = 8.4 Hz, 2H); 13C NMR DEPT (101 MHz, CDCl3): δ (p.p.m.) = 134.9 (2CHAr), 130.2 (CHAr), 129.9 (2CHAr), 128.8 (2CHAr), 126.5 (2CHAr), 124.1 (CHAr), 119.7 (2CHAr), 119 (2CHAr).

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.74490 (4)	0.10572 (13)	0.07643 (5)	0.0708 (3)
N3	0.69265 (12)	0.6140 (4)	0.19811 (11)	0.0507 (5)
N2	0.74402 (12)	0.4385 (4)	0.18506 (11)	0.0540 (5)
N1	0.64442 (12)	0.4567 (4)	0.09308 (11)	0.0539 (5)
C7	0.63379 (13)	0.6216 (4)	0.14328 (13)	0.0474 (5)
C6	0.56826 (8)	0.7865 (3)	0.13936 (9)	0.0518 (6)
C1	0.56878 (10)	0.9796 (3)	0.18563 (10)	0.0661 (7)
H1	0.6109	1.0031	0.2219	0.079*
C2	0.50635 (12)	1.1377 (3)	0.17765 (12)	0.0811 (9)
H2	0.5067	1.2669	0.2086	0.097*
C3	0.44340 (10)	1.1026 (4)	0.12341 (13)	0.0885 (11)
H3A	0.4016	1.2083	0.1181	0.106*
C4	0.44288 (9)	0.9094 (4)	0.07715 (11)	0.0903 (11)
H4	0.4008	0.8859	0.0409	0.108*
C5	0.50531 (11)	0.7514 (3)	0.08512 (10)	0.0746 (8)
H5	0.5050	0.6222	0.0542	0.090*
C9	0.85042 (16)	0.1109 (4)	0.09473 (14)	0.0575 (6)
C12	1.01532 (19)	0.0906 (5)	0.1147 (2)	0.0795 (9)
C8	0.71159 (14)	0.3513 (4)	0.12111 (13)	0.0508 (6)
C14	0.89725 (16)	0.2919 (5)	0.07283 (17)	0.0676 (7)
H14	0.8728	0.4205	0.0506	0.081*
C13	0.97963 (17)	0.2836 (5)	0.08361 (19)	0.0751 (8)
H13	1.0110	0.4074	0.0700	0.090*
C10	0.8872 (2)	−0.0810 (5)	0.12533 (18)	0.0750 (8)
H10	0.8562	−0.2039	0.1403	0.090*
C15	1.14533 (12)	0.2518 (3)	0.13117 (13)	0.0779 (9)
C16	1.20579 (14)	0.2829 (4)	0.08041 (11)	0.0981 (13)
H16	1.2114	0.1797	0.0407	0.118*
C17	1.25792 (12)	0.4683 (5)	0.08903 (12)	0.0986 (12)
H17	1.2984	0.4891	0.0551	0.118*
C18	1.24959 (12)	0.6225 (4)	0.14841 (16)	0.0937 (11)
H18	1.2845	0.7465	0.1542	0.112*
C19	1.18913 (14)	0.5914 (3)	0.19916 (12)	0.0873 (10)
H19	1.1836	0.6945	0.2389	0.105*
C20	1.13700 (11)	0.4060 (4)	0.19055 (12)	0.0786 (9)
H20	1.0966	0.3852	0.2245	0.094*
C11	0.9694 (2)	−0.0913 (5)	0.1338 (2)	0.0885 (10)
H11	0.9941	−0.2238	0.1527	0.106*
H3	0.7060 (16)	0.717 (5)	0.2355 (16)	0.070 (8)*
O1	1.09730 (15)	0.0639 (4)	0.1246 (2)	0.1279 (16)	0.997 (9)

	U11	U22	U33	U12	U13	U23
S1	0.0633 (5)	0.0627 (5)	0.0859 (5)	−0.0058 (3)	−0.0005 (4)	−0.0210 (4)
N3	0.0525 (11)	0.0532 (12)	0.0451 (11)	0.0006 (9)	−0.0107 (9)	−0.0013 (9)
N2	0.0555 (12)	0.0555 (12)	0.0496 (11)	0.0026 (10)	−0.0097 (9)	0.0026 (9)
N1	0.0519 (12)	0.0602 (12)	0.0485 (11)	−0.0047 (10)	−0.0077 (9)	−0.0014 (10)
C7	0.0451 (12)	0.0534 (14)	0.0431 (12)	−0.0078 (10)	−0.0040 (10)	0.0065 (10)
C6	0.0446 (12)	0.0599 (15)	0.0501 (13)	−0.0055 (11)	−0.0035 (10)	0.0106 (11)
C1	0.0546 (15)	0.0708 (18)	0.0727 (17)	0.0024 (14)	0.0016 (13)	0.0024 (15)
C2	0.0718 (19)	0.076 (2)	0.098 (2)	0.0122 (16)	0.0194 (17)	0.0087 (17)
C3	0.0581 (18)	0.104 (3)	0.104 (2)	0.0201 (18)	0.0124 (17)	0.043 (2)
C4	0.0576 (17)	0.124 (3)	0.087 (2)	0.0107 (19)	−0.0181 (16)	0.026 (2)
C5	0.0611 (17)	0.094 (2)	0.0662 (17)	−0.0001 (16)	−0.0168 (13)	0.0056 (16)
C9	0.0646 (16)	0.0480 (14)	0.0596 (15)	0.0014 (12)	−0.0005 (12)	−0.0038 (11)
C12	0.0659 (18)	0.0560 (18)	0.114 (3)	0.0176 (14)	−0.0201 (17)	−0.0137 (16)
C8	0.0505 (13)	0.0522 (14)	0.0492 (13)	−0.0070 (11)	−0.0020 (10)	0.0019 (11)
C14	0.0598 (16)	0.0539 (16)	0.088 (2)	0.0077 (13)	−0.0042 (14)	0.0132 (14)
C13	0.0616 (17)	0.0563 (17)	0.107 (2)	0.0024 (14)	−0.0034 (16)	0.0073 (16)
C10	0.087 (2)	0.0506 (16)	0.086 (2)	0.0012 (14)	−0.0052 (16)	0.0067 (14)
C15	0.0549 (16)	0.070 (2)	0.106 (2)	0.0231 (15)	−0.0157 (16)	−0.0158 (17)
C16	0.082 (2)	0.137 (4)	0.074 (2)	0.050 (2)	−0.0119 (18)	−0.029 (2)
C17	0.069 (2)	0.148 (4)	0.079 (2)	0.026 (2)	0.0060 (17)	0.027 (2)
C18	0.076 (2)	0.094 (3)	0.110 (3)	0.0044 (19)	−0.005 (2)	0.017 (2)
C19	0.081 (2)	0.085 (2)	0.096 (2)	0.0046 (18)	0.0003 (18)	−0.0168 (19)
C20	0.0653 (18)	0.083 (2)	0.088 (2)	0.0146 (16)	0.0087 (16)	−0.0074 (17)
C11	0.098 (2)	0.0485 (17)	0.116 (3)	0.0183 (17)	−0.028 (2)	0.0039 (16)
O1	0.0700 (17)	0.0667 (17)	0.242 (4)	0.0247 (12)	−0.0404 (18)	−0.0344 (18)

S1—C9	1.765 (3)	C12—C13	1.374 (4)
S1—C8	1.740 (3)	C12—C11	1.361 (5)
N3—N2	1.362 (3)	C12—O1	1.372 (4)
N3—C7	1.334 (3)	C14—H14	0.9300
N3—H3	0.91 (3)	C14—C13	1.372 (4)
N2—C8	1.320 (3)	C13—H13	0.9300
N1—C7	1.324 (3)	C10—H10	0.9300
N1—C8	1.344 (3)	C10—C11	1.366 (5)
C7—C6	1.453 (3)	C15—C16	1.3900
C6—C1	1.3900	C15—C20	1.3900
C6—C5	1.3900	C15—O1	1.359 (3)
C1—H1	0.9300	C16—H16	0.9300
C1—C2	1.3900	C16—C17	1.3900
C2—H2	0.9300	C17—H17	0.9300
C2—C3	1.3900	C17—C18	1.3900
C3—H3A	0.9300	C18—H18	0.9300
C3—C4	1.3900	C18—C19	1.3900
C4—H4	0.9300	C19—H19	0.9300
C4—C5	1.3900	C19—C20	1.3900
C5—H5	0.9300	C20—H20	0.9300
C9—C14	1.380 (4)	C11—H11	0.9300
C9—C10	1.372 (4)
C8—S1—C9	103.95 (12)	N2—C8—N1	115.2 (2)
N2—N3—H3	119.3 (18)	N1—C8—S1	119.43 (18)
C7—N3—N2	110.2 (2)	C9—C14—H14	119.7
C7—N3—H3	129.7 (18)	C13—C14—C9	120.5 (3)
C8—N2—N3	101.72 (19)	C13—C14—H14	119.7
C7—N1—C8	103.21 (19)	C12—C13—H13	120.4
N3—C7—C6	125.0 (2)	C14—C13—C12	119.3 (3)
N1—C7—N3	109.6 (2)	C14—C13—H13	120.4
N1—C7—C6	125.33 (19)	C9—C10—H10	120.0
C1—C6—C7	122.03 (14)	C11—C10—C9	120.0 (3)
C1—C6—C5	120.0	C11—C10—H10	120.0
C5—C6—C7	117.92 (14)	C16—C15—C20	120.0
C6—C1—H1	120.0	O1—C15—C16	119.5 (2)
C2—C1—C6	120.0	O1—C15—C20	120.4 (2)
C2—C1—H1	120.0	C15—C16—H16	120.0
C1—C2—H2	120.0	C15—C16—C17	120.0
C3—C2—C1	120.0	C17—C16—H16	120.0
C3—C2—H2	120.0	C16—C17—H17	120.0
C2—C3—H3A	120.0	C18—C17—C16	120.0
C2—C3—C4	120.0	C18—C17—H17	120.0
C4—C3—H3A	120.0	C17—C18—H18	120.0
C3—C4—H4	120.0	C19—C18—C17	120.0
C3—C4—C5	120.0	C19—C18—H18	120.0
C5—C4—H4	120.0	C18—C19—H19	120.0
C6—C5—H5	120.0	C18—C19—C20	120.0
C4—C5—C6	120.0	C20—C19—H19	120.0
C4—C5—H5	120.0	C15—C20—H20	120.0
C14—C9—S1	122.1 (2)	C19—C20—C15	120.0
C10—C9—S1	118.3 (2)	C19—C20—H20	120.0
C10—C9—C14	119.3 (3)	C12—C11—C10	120.6 (3)
C11—C12—C13	120.2 (3)	C12—C11—H11	119.7
C11—C12—O1	116.5 (3)	C10—C11—H11	119.7
O1—C12—C13	123.2 (3)	C15—O1—C12	119.5 (2)
N2—C8—S1	125.17 (19)
S1—C9—C14—C13	−175.8 (2)	C9—C10—C11—C12	2.4 (5)
S1—C9—C10—C11	174.0 (3)	C8—S1—C9—C14	−57.9 (3)
N3—N2—C8—S1	−175.31 (18)	C8—S1—C9—C10	128.3 (2)
N3—N2—C8—N1	−0.1 (3)	C8—N1—C7—N3	0.4 (3)
N3—C7—C6—C1	12.0 (3)	C8—N1—C7—C6	−179.7 (2)
N3—C7—C6—C5	−170.67 (19)	C14—C9—C10—C11	0.0 (5)
N2—N3—C7—N1	−0.5 (3)	C13—C12—C11—C10	−2.8 (6)
N2—N3—C7—C6	179.66 (19)	C13—C12—O1—C15	24.8 (5)
N1—C7—C6—C1	−167.84 (18)	C10—C9—C14—C13	−2.0 (4)
N1—C7—C6—C5	9.5 (3)	C15—C16—C17—C18	0.0
C7—N3—N2—C8	0.4 (2)	C16—C15—C20—C19	0.0
C7—N1—C8—S1	175.31 (17)	C16—C15—O1—C12	−122.6 (3)
C7—N1—C8—N2	−0.2 (3)	C16—C17—C18—C19	0.0
C7—C6—C1—C2	177.32 (18)	C17—C18—C19—C20	0.0
C7—C6—C5—C4	−177.43 (17)	C18—C19—C20—C15	0.0
C6—C1—C2—C3	0.0	C20—C15—C16—C17	0.0
C1—C6—C5—C4	0.0	C20—C15—O1—C12	60.7 (4)
C1—C2—C3—C4	0.0	C11—C12—C13—C14	0.8 (5)
C2—C3—C4—C5	0.0	C11—C12—O1—C15	−158.7 (3)
C3—C4—C5—C6	0.0	O1—C12—C13—C14	177.2 (3)
C5—C6—C1—C2	0.0	O1—C12—C11—C10	−179.5 (3)
C9—S1—C8—N2	−34.3 (2)	O1—C15—C16—C17	−176.7 (2)
C9—S1—C8—N1	150.7 (2)	O1—C15—C20—C19	176.7 (2)
C9—C14—C13—C12	1.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2i	0.91 (3)	2.05 (3)	2.944 (3)	170 (2)
C16—H16···S1ii	0.93	2.77	3.694 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N2i	0.91 (3)	2.05 (3)	2.944 (3)	170 (2)
C16—H16⋯S1ii	0.93	2.77	3.694 (2)	170

Symmetry codes: (i) ; (ii) .