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

Fun, H.-K.; Yeap, C.S.; Manjunath, K.; Prasad, D.J.; Poojary, B.

doi:10.1107/S1600536811027565

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2063

doi:10.1107/S1600536811027565

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

Hoong-Kun Fun,^a ^*‡ Chin Sing Yeap,^a § K Manjunath,^b D. Jagadeesh Prasad ^b and Boja Poojary ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Mangalore University, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 4 July 2011; accepted 9 July 2011; online 16 July 2011)

In the title molecule, C₂₄H₂₁ClN₄OS₂, 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 methylsulfanyl-substituted benzene ring and the phenyl ring, respectively. In the crystal, molecules are linked into sheets parallel to (100) by intermolecular 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_r = 481.02
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.159
S = 1.05
7900 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.45 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811027565/lh5283sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811027565/lh5283Isup3.cml

checkCIF report

Comment top

1,2,4-Triazole compounds show a broad spectrum of biological activities, possibly due to the presence of the N–C–S group (Holla et al., 2002). Among the 1,2,4-triazoles, the mercapto-thione-substituted 1,2,4-triazole ring systems have been well studied and so far, a variety of biological activities have been reported for a large number of their derivatives, such as antibacterial (Burch & Smith, 1966), antifungal (Kalyoncuoglu et al., 1992), antitubercular (Mir et al., 1970), antimycobacterial (Rudnicka et al., 1986), anticancer (Holla et al., 2003) and hypoglycemic properties (Mhasalkar et al., 1970). In view of the above findings, and in continuation of our earlier work on the synthesis and biological activity of triazoles and their derivatives, we have synthesized a series of 1,2,4-triazole derivatives via joining a 1,2,4-triazole and acylamide group together in the same molecule and have studied their biological activities. As part of this research we have determined the crystal structure of th title compound.

The molecular structure of the title compound (I) is shown in Fig. 1. The central 1,2,4-triazole ring forms dihedral angles of 89.05 (9), 86.66 (9) and 82.70 (10)° with the three benzene rings (C1–C6, C18–C23 and C12–C17). In the crystal, molecules are linked into double sheets parallel to (1 0 0) by intermolecular N1—H1N1···N3ⁱ, C8—H8A···O1ⁱⁱ and C11—H11B···O1ⁱⁱⁱ hydrogen bonds (Table 1, Fig. 2).

Related literature top

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 top

A equimolar mixture of 5-[4-(methylthiobenzyl]-4-phenyl-4H-[1,2,4]-triazole-3-thione (0.01 mol), 2-Chloro-N-(2-chlorophenyl)acetamide (0.01 mol) and dry potassium carbonate (0.01 mol) were refluxed for 6 h in 20 ml of absolute alcohol and excess of solvent was removed by distillation under reduced pressure. After cooling to room temperature, the reaction mixture was poured into 50 ml of water. The product which precipitated was filtered off, washed with methanol and dried. The crude product was re-crystallized from ethanol.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of (I), showing the molecules linked into a double sheets parallel to (1 0 0). Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₂₄H₂₁ClN₄OS₂	F(000) = 1000
M_r = 481.02	D_x = 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

Data collection top

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

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.075P)² + 0.4271P] where P = (F_o² + 2F_c²)/3
7900 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₂₄H₂₁ClN₄OS₂	V = 2349.6 (2) Å³
M_r = 481.02	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.2542 (7) Å	µ = 0.37 mm⁻¹
b = 16.3273 (9) Å	T = 297 K
c = 10.1584 (6) Å	0.52 × 0.27 × 0.22 mm
β = 96.372 (1)°

Data collection top

Bruker APEXII DUO CCD diffractometer	7900 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5235 reflections with I > 2σ(I)
T_min = 0.832, T_max = 0.924	R_int = 0.028
29877 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.05	Δρ_max = 0.53 e Å⁻³
7900 reflections	Δρ_min = −0.45 e Å⁻³
290 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	0.90496 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₁ClN₄OS₂
M_r	481.02
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	297
a, b, c (Å)	14.2542 (7), 16.3273 (9), 10.1584 (6)
β (°)	96.372 (1)
V (Å³)	2349.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.52 × 0.27 × 0.22

Data collection
Diffractometer	Bruker APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.832, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	29877, 7900, 5235
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.739

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.159, 1.05
No. of reflections	7900
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.45

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+1, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5523-2009.

Acknowledgements

HKF and CSY thank Universiti Sains Malaysia for the Research University Grant 1001/PFIZIK/811160.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burch, H. A. & Smith, W. O. (1966). J. Med. Chem. 9, 405–408. CrossRef CAS PubMed Web of Science Google Scholar
Holla, B. S., Poojary, K. N., Rao, B. S. & Shivananda, M. K. (2002). Eur. J. Med. Chem. 37, 511–517. CrossRef PubMed Google Scholar
Holla, B. S., Veerendra, B., Shivananda, M. K. & Poojary, B. (2003). Eur. J. Med. Chem. 38, 759–767. Web of Science CrossRef PubMed Google Scholar
Kalyoncuoglu, N., Rollas, S., Sür-Altiner, D., Yegenoglu, Y. & Ang, Ö. (1992). Pharmazie, 47, 796–797. PubMed CAS Web of Science Google Scholar
Mhasalkar, M. Y., Shah, M. H., Nikam, S. T., Anantanarayanan, K. G. & Deliwala, C. V. (1970). J. Med. Chem. 13, 672–674. CrossRef CAS PubMed Web of Science Google Scholar
Mir, I., Siddiqui, M. T. & Comrie, A. (1970). Tetrahedron, 26, 5235–5238. CrossRef CAS PubMed Web of Science Google Scholar
Rudnicka, W., Foks, H., Janowiec, M. & Zwolska-Kwiek, Z. (1986). Acta Pol. Pharm. 43, 523–528. CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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