N-(2-Chloro-phen-yl)-2-({5-[4-(methyl-sulfan-yl)benz-yl]-4-phenyl-4H-1,2,4-triazol-3-yl}sulfan-yl)acetamide.

In the title mol-ecule, C(24)H(21)ClN(4)OS(2), the central 1,2,4-triazole ring forms dihedral angles of 89.05 (9), 86.66 (9) and 82.70 (10)° with the chloro-substituted benzene ring, the methyl-sulfanyl-substituted benzene ring and the phenyl ring, respectively. In the crystal, mol-ecules are linked into sheets parallel to (100) by inter-molecular N-H⋯N and weak C-H⋯O hydrogen bonds.

Related literature

For general background to and applications of 1,2,4-triazole derivatives, see: Holla et al. (2002 ▶, 2003 ▶); Rudnicka et al. (1986 ▶); Burch & Smith (1966 ▶); Kalyoncuoglu et al. (1992 ▶); Mhasalkar et al. (1970 ▶); Mir et al. (1970 ▶).

Experimental

Crystal data

C24H21ClN4OS2

M = 481.02

Monoclinic,

a = 14.2542 (7) Å

b = 16.3273 (9) Å

c = 10.1584 (6) Å

β = 96.372 (1)°

V = 2349.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 297 K

0.52 × 0.27 × 0.22 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.832, T max = 0.924

29877 measured reflections

7900 independent reflections

5235 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.159

S = 1.05

7900 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811027565/lh5283sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027565/lh5283Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027565/lh5283Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H21ClN4OS2	F(000) = 1000
Mr = 481.02	Dx = 1.360 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7952 reflections
a = 14.2542 (7) Å	θ = 2.5–30.4°
b = 16.3273 (9) Å	µ = 0.37 mm−1
c = 10.1584 (6) Å	T = 297 K
β = 96.372 (1)°	Block, brown
V = 2349.6 (2) Å3	0.52 × 0.27 × 0.22 mm
Z = 4

Bruker APEXII DUO CCD diffractometer	7900 independent reflections
Radiation source: fine-focus sealed tube	5235 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 31.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→21
Tmin = 0.832, Tmax = 0.924	k = −24→23
29877 measured reflections	l = −14→14

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.075P)2 + 0.4271P] where P = (Fo2 + 2Fc2)/3
7900 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.90496 (5)	0.48639 (5)	1.17911 (9)	0.1088 (3)
S1	0.39474 (3)	0.45413 (3)	0.74551 (4)	0.05346 (13)
S2	0.00345 (5)	0.24018 (6)	0.06766 (9)	0.1109 (3)
O1	0.58819 (9)	0.47636 (7)	0.90982 (12)	0.0551 (3)
N1	0.59354 (9)	0.34760 (8)	0.99633 (14)	0.0483 (3)
H1N1	0.5589	0.2988	0.9997	0.058*
N2	0.48488 (9)	0.33585 (8)	0.61649 (13)	0.0469 (3)
N3	0.48455 (9)	0.30835 (8)	0.48666 (14)	0.0467 (3)
N4	0.38196 (8)	0.40807 (7)	0.48700 (12)	0.0393 (3)
C1	0.74454 (12)	0.40977 (11)	1.08375 (18)	0.0534 (4)
H1A	0.7464	0.4416	1.0081	0.064*
C2	0.81439 (13)	0.41592 (12)	1.1889 (2)	0.0623 (5)
C3	0.81517 (16)	0.36979 (15)	1.3012 (2)	0.0758 (6)
H3A	0.8632	0.3754	1.3704	0.091*
C4	0.74302 (16)	0.31485 (16)	1.3089 (2)	0.0766 (6)
H4A	0.7421	0.2828	1.3844	0.092*
C5	0.67174 (13)	0.30652 (12)	1.20593 (19)	0.0598 (4)
H5A	0.6239	0.2684	1.2119	0.072*
C6	0.67148 (11)	0.35481 (10)	1.09415 (16)	0.0449 (3)
C7	0.55154 (11)	0.41050 (10)	0.92502 (14)	0.0420 (3)
C8	0.44971 (11)	0.39121 (11)	0.87723 (15)	0.0469 (3)
H8A	0.4132	0.3957	0.9520	0.056*
H8B	0.4462	0.3346	0.8479	0.056*
C9	0.42302 (10)	0.39516 (9)	0.61317 (15)	0.0410 (3)
C10	0.42372 (10)	0.35210 (9)	0.41135 (15)	0.0411 (3)
C11	0.40297 (11)	0.34559 (11)	0.26504 (15)	0.0457 (3)
H11A	0.4454	0.3056	0.2332	0.055*
H11B	0.4161	0.3980	0.2260	0.055*
C12	0.30248 (11)	0.32128 (10)	0.21711 (15)	0.0429 (3)
C13	0.26102 (13)	0.25277 (12)	0.2653 (2)	0.0605 (5)
H13A	0.2949	0.2215	0.3308	0.073*
C14	0.17027 (15)	0.22984 (13)	0.2183 (2)	0.0679 (5)
H14A	0.1439	0.1834	0.2525	0.081*
C15	0.11798 (13)	0.27517 (13)	0.1210 (2)	0.0615 (5)
C16	0.15828 (14)	0.34441 (14)	0.0742 (2)	0.0656 (5)
H16A	0.1239	0.3765	0.0104	0.079*
C17	0.24971 (13)	0.36663 (12)	0.12152 (17)	0.0549 (4)
H17A	0.2760	0.4132	0.0879	0.066*
C18	0.30298 (10)	0.46012 (9)	0.44437 (14)	0.0411 (3)
C19	0.21336 (12)	0.43210 (13)	0.4587 (2)	0.0587 (4)
H19A	0.2049	0.3821	0.4996	0.070*
C20	0.13671 (15)	0.47902 (18)	0.4118 (3)	0.0819 (7)
H20A	0.0760	0.4605	0.4207	0.098*
C21	0.14890 (19)	0.55153 (18)	0.3532 (3)	0.0894 (8)
H21A	0.0965	0.5827	0.3219	0.107*
C22	0.2370 (2)	0.57963 (15)	0.3394 (3)	0.0892 (8)
H22A	0.2444	0.6300	0.2991	0.107*
C23	0.31656 (15)	0.53345 (12)	0.3851 (2)	0.0634 (5)
H23A	0.3770	0.5522	0.3753	0.076*
C24	−0.04042 (19)	0.3111 (2)	−0.0555 (3)	0.1131 (11)
H24A	−0.1055	0.2992	−0.0837	0.170*
H24B	−0.0045	0.3070	−0.1298	0.170*
H24C	−0.0351	0.3655	−0.0199	0.170*

	U11	U22	U33	U12	U13	U23
Cl1	0.0754 (4)	0.0927 (5)	0.1462 (7)	−0.0411 (3)	−0.0421 (4)	0.0276 (4)
S1	0.0579 (2)	0.0499 (2)	0.0494 (2)	0.01375 (18)	−0.00817 (17)	−0.00946 (17)
S2	0.0727 (4)	0.1321 (7)	0.1206 (6)	−0.0488 (4)	−0.0226 (4)	0.0262 (5)
O1	0.0541 (7)	0.0477 (6)	0.0610 (7)	−0.0125 (5)	−0.0046 (5)	0.0102 (5)
N1	0.0456 (7)	0.0414 (7)	0.0549 (8)	−0.0092 (5)	−0.0071 (6)	0.0032 (6)
N2	0.0430 (6)	0.0449 (7)	0.0501 (7)	0.0090 (5)	−0.0070 (5)	−0.0012 (5)
N3	0.0435 (6)	0.0438 (7)	0.0514 (7)	0.0092 (5)	−0.0011 (5)	−0.0027 (5)
N4	0.0355 (5)	0.0386 (6)	0.0422 (6)	0.0057 (5)	−0.0031 (4)	0.0006 (5)
C1	0.0454 (8)	0.0511 (10)	0.0610 (10)	−0.0068 (7)	−0.0060 (7)	0.0050 (8)
C2	0.0498 (9)	0.0520 (10)	0.0803 (13)	−0.0091 (8)	−0.0139 (8)	0.0001 (9)
C3	0.0683 (12)	0.0763 (14)	0.0750 (14)	−0.0042 (11)	−0.0275 (10)	0.0053 (11)
C4	0.0702 (13)	0.0887 (16)	0.0660 (12)	−0.0067 (12)	−0.0148 (10)	0.0232 (11)
C5	0.0512 (9)	0.0600 (11)	0.0660 (11)	−0.0051 (8)	−0.0036 (8)	0.0141 (9)
C6	0.0418 (7)	0.0409 (8)	0.0506 (8)	−0.0007 (6)	−0.0018 (6)	−0.0011 (6)
C7	0.0441 (7)	0.0438 (8)	0.0374 (7)	−0.0051 (6)	0.0011 (5)	−0.0029 (6)
C8	0.0456 (8)	0.0518 (9)	0.0417 (7)	−0.0062 (7)	−0.0027 (6)	−0.0006 (6)
C9	0.0374 (6)	0.0390 (7)	0.0444 (7)	0.0031 (5)	−0.0055 (5)	−0.0004 (6)
C10	0.0369 (6)	0.0397 (7)	0.0460 (7)	0.0030 (5)	0.0018 (5)	0.0000 (6)
C11	0.0423 (7)	0.0505 (9)	0.0445 (8)	0.0019 (6)	0.0053 (6)	−0.0005 (6)
C12	0.0438 (7)	0.0431 (8)	0.0416 (7)	0.0019 (6)	0.0048 (6)	−0.0021 (6)
C13	0.0519 (9)	0.0537 (10)	0.0751 (12)	0.0041 (8)	0.0031 (8)	0.0194 (9)
C14	0.0589 (10)	0.0519 (11)	0.0925 (15)	−0.0084 (9)	0.0071 (10)	0.0148 (10)
C15	0.0524 (9)	0.0702 (12)	0.0605 (10)	−0.0134 (9)	−0.0004 (8)	−0.0018 (9)
C16	0.0596 (10)	0.0783 (13)	0.0546 (10)	−0.0111 (9)	−0.0126 (8)	0.0179 (9)
C17	0.0555 (9)	0.0586 (10)	0.0485 (9)	−0.0116 (8)	−0.0032 (7)	0.0109 (7)
C18	0.0399 (7)	0.0406 (7)	0.0410 (7)	0.0090 (6)	−0.0034 (5)	0.0006 (6)
C19	0.0411 (8)	0.0640 (11)	0.0698 (11)	0.0058 (8)	0.0014 (7)	0.0052 (9)
C20	0.0452 (10)	0.1068 (19)	0.0905 (16)	0.0244 (11)	−0.0069 (10)	−0.0045 (14)
C21	0.0787 (16)	0.0984 (19)	0.0846 (16)	0.0471 (14)	−0.0195 (12)	−0.0029 (14)
C22	0.120 (2)	0.0542 (12)	0.0880 (16)	0.0259 (13)	−0.0135 (15)	0.0193 (11)
C23	0.0667 (11)	0.0490 (10)	0.0731 (12)	0.0034 (8)	0.0010 (9)	0.0127 (8)
C24	0.0639 (14)	0.157 (3)	0.111 (2)	−0.0165 (17)	−0.0253 (14)	0.011 (2)

Cl1—C2	1.740 (2)	C10—C11	1.487 (2)
S1—C9	1.7371 (16)	C11—C12	1.514 (2)
S1—C8	1.7964 (16)	C11—H11A	0.9700
S2—C15	1.7574 (19)	C11—H11B	0.9700
S2—C24	1.767 (3)	C12—C17	1.377 (2)
O1—C7	1.2128 (19)	C12—C13	1.380 (2)
N1—C7	1.357 (2)	C13—C14	1.380 (3)
N1—C6	1.411 (2)	C13—H13A	0.9300
N1—H1N1	0.9408	C14—C15	1.385 (3)
N2—C9	1.3075 (19)	C14—H14A	0.9300
N2—N3	1.3927 (19)	C15—C16	1.376 (3)
N3—C10	1.3038 (19)	C16—C17	1.386 (3)
N4—C9	1.3650 (18)	C16—H16A	0.9300
N4—C10	1.3717 (19)	C17—H17A	0.9300
N4—C18	1.4383 (17)	C18—C23	1.364 (2)
C1—C2	1.380 (2)	C18—C19	1.380 (2)
C1—C6	1.388 (2)	C19—C20	1.375 (3)
C1—H1A	0.9300	C19—H19A	0.9300
C2—C3	1.366 (3)	C20—C21	1.345 (4)
C3—C4	1.374 (3)	C20—H20A	0.9300
C3—H3A	0.9300	C21—C22	1.358 (4)
C4—C5	1.381 (3)	C21—H21A	0.9300
C4—H4A	0.9300	C22—C23	1.398 (3)
C5—C6	1.382 (2)	C22—H22A	0.9300
C5—H5A	0.9300	C23—H23A	0.9300
C7—C8	1.512 (2)	C24—H24A	0.9600
C8—H8A	0.9700	C24—H24B	0.9600
C8—H8B	0.9700	C24—H24C	0.9600
C9—S1—C8	98.04 (7)	C10—C11—H11B	108.6
C15—S2—C24	104.42 (12)	C12—C11—H11B	108.6
C7—N1—C6	125.38 (13)	H11A—C11—H11B	107.6
C7—N1—H1N1	117.3	C17—C12—C13	117.67 (15)
C6—N1—H1N1	114.9	C17—C12—C11	120.62 (15)
C9—N2—N3	106.43 (12)	C13—C12—C11	121.71 (15)
C10—N3—N2	108.13 (12)	C14—C13—C12	121.26 (17)
C9—N4—C10	104.81 (11)	C14—C13—H13A	119.4
C9—N4—C18	127.86 (12)	C12—C13—H13A	119.4
C10—N4—C18	126.78 (12)	C13—C14—C15	120.78 (18)
C2—C1—C6	118.11 (17)	C13—C14—H14A	119.6
C2—C1—H1A	120.9	C15—C14—H14A	119.6
C6—C1—H1A	120.9	C16—C15—C14	118.25 (17)
C3—C2—C1	122.97 (18)	C16—C15—S2	124.72 (16)
C3—C2—Cl1	118.34 (15)	C14—C15—S2	117.02 (15)
C1—C2—Cl1	118.68 (16)	C15—C16—C17	120.50 (18)
C2—C3—C4	118.09 (18)	C15—C16—H16A	119.8
C2—C3—H3A	121.0	C17—C16—H16A	119.8
C4—C3—H3A	121.0	C12—C17—C16	121.53 (17)
C3—C4—C5	120.9 (2)	C12—C17—H17A	119.2
C3—C4—H4A	119.5	C16—C17—H17A	119.2
C5—C4—H4A	119.5	C23—C18—C19	121.08 (16)
C4—C5—C6	120.03 (18)	C23—C18—N4	120.47 (15)
C4—C5—H5A	120.0	C19—C18—N4	118.37 (14)
C6—C5—H5A	120.0	C20—C19—C18	119.2 (2)
C5—C6—C1	119.86 (15)	C20—C19—H19A	120.4
C5—C6—N1	117.46 (15)	C18—C19—H19A	120.4
C1—C6—N1	122.64 (15)	C21—C20—C19	120.4 (2)
O1—C7—N1	124.62 (14)	C21—C20—H20A	119.8
O1—C7—C8	123.76 (15)	C19—C20—H20A	119.8
N1—C7—C8	111.39 (13)	C20—C21—C22	120.6 (2)
C7—C8—S1	116.35 (12)	C20—C21—H21A	119.7
C7—C8—H8A	108.2	C22—C21—H21A	119.7
S1—C8—H8A	108.2	C21—C22—C23	120.6 (2)
C7—C8—H8B	108.2	C21—C22—H22A	119.7
S1—C8—H8B	108.2	C23—C22—H22A	119.7
H8A—C8—H8B	107.4	C18—C23—C22	118.1 (2)
N2—C9—N4	110.87 (13)	C18—C23—H23A	121.0
N2—C9—S1	127.18 (11)	C22—C23—H23A	121.0
N4—C9—S1	121.93 (11)	S2—C24—H24A	109.5
N3—C10—N4	109.75 (13)	S2—C24—H24B	109.5
N3—C10—C11	126.37 (14)	H24A—C24—H24B	109.5
N4—C10—C11	123.86 (13)	S2—C24—H24C	109.5
C10—C11—C12	114.61 (13)	H24A—C24—H24C	109.5
C10—C11—H11A	108.6	H24B—C24—H24C	109.5
C12—C11—H11A	108.6
C9—N2—N3—C10	0.44 (17)	C9—N4—C10—C11	−177.83 (14)
C6—C1—C2—C3	0.8 (3)	C18—N4—C10—C11	10.2 (2)
C6—C1—C2—Cl1	−178.42 (14)	N3—C10—C11—C12	117.85 (17)
C1—C2—C3—C4	0.1 (4)	N4—C10—C11—C12	−64.0 (2)
Cl1—C2—C3—C4	179.4 (2)	C10—C11—C12—C17	128.51 (17)
C2—C3—C4—C5	0.0 (4)	C10—C11—C12—C13	−52.5 (2)
C3—C4—C5—C6	−1.1 (4)	C17—C12—C13—C14	0.8 (3)
C4—C5—C6—C1	2.1 (3)	C11—C12—C13—C14	−178.17 (18)
C4—C5—C6—N1	−175.7 (2)	C12—C13—C14—C15	0.0 (3)
C2—C1—C6—C5	−1.9 (3)	C13—C14—C15—C16	−1.2 (3)
C2—C1—C6—N1	175.77 (17)	C13—C14—C15—S2	179.65 (18)
C7—N1—C6—C5	141.23 (18)	C24—S2—C15—C16	1.5 (3)
C7—N1—C6—C1	−36.5 (3)	C24—S2—C15—C14	−179.4 (2)
C6—N1—C7—O1	20.1 (3)	C14—C15—C16—C17	1.6 (3)
C6—N1—C7—C8	−154.53 (15)	S2—C15—C16—C17	−179.32 (17)
O1—C7—C8—S1	22.1 (2)	C13—C12—C17—C16	−0.4 (3)
N1—C7—C8—S1	−163.17 (12)	C11—C12—C17—C16	178.58 (18)
C9—S1—C8—C7	90.32 (13)	C15—C16—C17—C12	−0.8 (3)
N3—N2—C9—N4	−0.06 (17)	C9—N4—C18—C23	104.7 (2)
N3—N2—C9—S1	−178.58 (12)	C10—N4—C18—C23	−85.2 (2)
C10—N4—C9—N2	−0.32 (17)	C9—N4—C18—C19	−78.7 (2)
C18—N4—C9—N2	171.54 (14)	C10—N4—C18—C19	91.5 (2)
C10—N4—C9—S1	178.29 (11)	C23—C18—C19—C20	0.3 (3)
C18—N4—C9—S1	−9.9 (2)	N4—C18—C19—C20	−176.41 (18)
C8—S1—C9—N2	−14.31 (16)	C18—C19—C20—C21	−0.3 (4)
C8—S1—C9—N4	167.32 (13)	C19—C20—C21—C22	0.0 (4)
N2—N3—C10—N4	−0.65 (17)	C20—C21—C22—C23	0.4 (4)
N2—N3—C10—C11	177.73 (14)	C19—C18—C23—C22	0.1 (3)
C9—N4—C10—N3	0.60 (17)	N4—C18—C23—C22	176.72 (19)
C18—N4—C10—N3	−171.37 (14)	C21—C22—C23—C18	−0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N3i	0.94	2.04	2.9787 (19)	174
C8—H8A···O1ii	0.97	2.52	3.147 (2)	123
C11—H11B···O1iii	0.97	2.47	3.416 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N3i	0.94	2.04	2.9787 (19)	174
C8—H8A⋯O1ii	0.97	2.52	3.147 (2)	123
C11—H11B⋯O1iii	0.97	2.47	3.416 (2)	165

Symmetry codes: (i) ; (ii) ; (iii) .