2-Benzoylmethyl-4-[(2-benzylidene-ethylidene)amino]-5-(2-thienylmethyl)-2H-1,2,4-triazol-3(4H)-one.

In the mol-ecule of the title compound, C(24)H(20)N(4)O(2)S, the dihedral angle between the triazole and thio-phene rings is 66.80 (4)° and the dihedral angle between the two benzene rings is 63.37 (4)°. An intra-molecular C-H⋯O inter-action results in the formation of a six-membered ring. A π⋯π contact between the benzene rings, [centroid-centroid distance = 3.918 (2) Å] may stabilize the structure. Weak C-H⋯π inter-actions are also present. The S, C and H atoms of the thiophene ring are disordered over two positions and were refined with occupancies of 0.654 (3) and 0.346 (3).

Related literature

For general background to 1,2,4-triazoles, see: Clemons et al. (2004 ▶); Colanceska-Ragenovic et al. (2001 ▶); Goss & Strasser-Weippl (2004 ▶); Santen (2003 ▶); Tsukuda et al. (1998 ▶); Ünver et al. (2008 ▶); Zhu et al. (2000 ▶). For related structucres, see: Çoruh et al. (2003 ▶); Ünver et al. (2006 ▶); Yılmaz et al. (2006 ▶); Vrábel et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C24H20N4O2S

M = 428.50

Monoclinic,

a = 17.4972 (3) Å

b = 14.7609 (3) Å

c = 8.2724 (1) Å

β = 96.395 (1)°

V = 2123.25 (6) Å3

Z = 4

Cu Kα radiation

μ = 1.59 mm−1

T = 294 K

0.30 × 0.11 × 0.07 mm

Data collection

Bruker CCD 6000 area-detector diffractometer

Absorption correction: none

10706 measured reflections

3697 independent reflections

2561 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.175

S = 1.06

3697 reflections

314 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012719/hk2655sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012719/hk2655Isup2.hkl

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

C24H20N4O2S	F(000) = 896
Mr = 428.50	Dx = 1.340 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 2561 reflections
a = 17.4972 (3) Å	θ = 2.5–68.2°
b = 14.7609 (3) Å	µ = 1.59 mm−1
c = 8.2724 (1) Å	T = 294 K
β = 96.395 (1)°	Prism, colorless
V = 2123.25 (6) Å3	0.30 × 0.11 × 0.07 mm
Z = 4

Bruker CCD 6000 area-detector diffractometer	2561 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
graphite	θmax = 68.2°, θmin = 2.5°
φ and ω scans	h = −20→18
10706 measured reflections	k = −16→16
3697 independent reflections	l = −9→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H-atom parameters constrained
wR(F2) = 0.175	w = 1/[σ2(Fo2) + (0.1091P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3697 reflections	Δρmax = 0.40 e Å−3
314 parameters	Δρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
S1	0.58098 (11)	0.41692 (13)	0.0657 (3)	0.0861 (6)	0.654 (3)
S1'	0.6146 (4)	0.2606 (4)	0.2561 (8)	0.0857 (11)	0.346 (3)
O1	0.88146 (9)	0.54521 (11)	0.47227 (19)	0.0690 (5)
O2	0.83595 (10)	0.40286 (12)	0.7644 (2)	0.0831 (5)
N1	0.86815 (11)	0.38928 (12)	0.4521 (2)	0.0637 (5)
N2	0.82649 (11)	0.32716 (12)	0.3517 (2)	0.0649 (5)
N4	0.79359 (10)	0.46712 (11)	0.2811 (2)	0.0535 (4)
N41	0.75222 (11)	0.53233 (12)	0.1882 (2)	0.0599 (5)
C3	0.78325 (13)	0.37638 (15)	0.2497 (3)	0.0580 (6)
C5	0.85161 (13)	0.47661 (15)	0.4121 (3)	0.0564 (5)
C11	0.92508 (14)	0.36161 (16)	0.5806 (3)	0.0660 (6)
H11A	0.9728	0.3932	0.5693	0.079*
H11B	0.9345	0.2972	0.5705	0.079*
C12	0.90121 (14)	0.38067 (14)	0.7490 (3)	0.0598 (6)
C13	0.96094 (13)	0.37260 (13)	0.8891 (3)	0.0559 (5)
C14	0.94621 (16)	0.40534 (15)	1.0407 (3)	0.0672 (7)
H14	0.8981	0.4297	1.0527	0.081*
C15	1.00083 (17)	0.40240 (17)	1.1714 (3)	0.0744 (7)
H15	0.9899	0.4253	1.2710	0.089*
C16	1.07174 (17)	0.36594 (18)	1.1572 (3)	0.0775 (7)
H16	1.1090	0.3639	1.2465	0.093*
C17	1.08709 (17)	0.3324 (2)	1.0088 (3)	0.0839 (8)
H17	1.1348	0.3066	0.9984	0.101*
C18	1.03279 (15)	0.33661 (16)	0.8763 (3)	0.0727 (7)
H18	1.0445	0.3149	0.7765	0.087*
C31	0.72983 (14)	0.34018 (16)	0.1113 (3)	0.0687 (6)
H31A	0.7351	0.3766	0.0155	0.082*
H31B	0.7453	0.2789	0.0882	0.082*
C32	0.64725 (15)	0.33916 (15)	0.1403 (3)	0.07042 (8)	0.654 (3)
C32'	0.64725 (15)	0.33916 (15)	0.1403 (3)	0.07042 (8)	0.346 (3)
C33	0.6141 (7)	0.2793 (8)	0.2307 (16)	0.0822 (19)	0.654 (3)
H33	0.6421	0.2322	0.2832	0.099*	0.654 (3)
C33'	0.5934 (8)	0.3931 (9)	0.070 (2)	0.086 (2)	0.346 (3)
H33'	0.6037	0.4378	−0.0036	0.103*	0.346 (3)
C34	0.5342 (4)	0.2905 (7)	0.2437 (14)	0.0834 (15)	0.654 (3)
H34	0.5044	0.2528	0.3015	0.100*	0.654 (3)
C34'	0.5184 (7)	0.3780 (12)	0.116 (2)	0.086 (2)	0.346 (3)
H34'	0.4743	0.4109	0.0809	0.103*	0.346 (3)
C35	0.5090 (4)	0.3640 (6)	0.1591 (9)	0.0847 (17)	0.654 (3)
H35	0.4585	0.3844	0.1512	0.102*	0.654 (3)
C35'	0.5228 (7)	0.3073 (13)	0.219 (3)	0.082 (2)	0.346 (3)
H35'	0.4807	0.2855	0.2670	0.099*	0.346 (3)
C42	0.75715 (13)	0.61382 (15)	0.2406 (3)	0.0598 (6)
H42	0.7884	0.6271	0.3361	0.072*
C43	0.71480 (13)	0.68498 (15)	0.1530 (3)	0.0605 (6)
H43	0.6822	0.6705	0.0600	0.073*
C44	0.72076 (13)	0.77056 (15)	0.2004 (3)	0.0637 (6)
H44	0.7551	0.7813	0.2925	0.076*
C45	0.68128 (13)	0.85043 (15)	0.1292 (3)	0.0586 (6)
C46	0.62026 (14)	0.84499 (17)	0.0066 (3)	0.0675 (6)
H46	0.6026	0.7886	−0.0312	0.081*
C47	0.58586 (16)	0.9221 (2)	−0.0589 (4)	0.0826 (8)
H47	0.5453	0.9176	−0.1412	0.099*
C48	0.61094 (17)	1.0064 (2)	−0.0037 (4)	0.0878 (8)
H48	0.5874	1.0585	−0.0487	0.105*
C49	0.67029 (17)	1.01301 (18)	0.1166 (4)	0.0893 (8)
H49	0.6873	1.0697	0.1542	0.107*
C50	0.70537 (16)	0.93594 (17)	0.1831 (3)	0.0765 (7)
H50	0.7459	0.9413	0.2654	0.092*

	U11	U22	U33	U12	U13	U23
S1	0.0805 (10)	0.0722 (11)	0.1040 (9)	0.0136 (6)	0.0029 (7)	0.0105 (8)
S1'	0.100 (2)	0.075 (2)	0.0847 (19)	−0.0139 (15)	0.0221 (15)	0.0089 (14)
O1	0.0746 (11)	0.0566 (10)	0.0731 (10)	−0.0050 (7)	−0.0033 (8)	−0.0049 (8)
O2	0.0659 (12)	0.0931 (13)	0.0922 (12)	0.0176 (9)	0.0176 (10)	0.0168 (9)
N1	0.0714 (13)	0.0495 (11)	0.0679 (11)	0.0034 (9)	−0.0022 (10)	−0.0017 (9)
N2	0.0706 (14)	0.0505 (11)	0.0725 (12)	0.0013 (9)	0.0039 (10)	−0.0048 (9)
N4	0.0555 (11)	0.0472 (11)	0.0577 (10)	0.0027 (7)	0.0052 (8)	−0.0001 (8)
N41	0.0625 (12)	0.0545 (12)	0.0623 (10)	0.0014 (8)	0.0055 (9)	0.0053 (9)
C3	0.0605 (14)	0.0507 (13)	0.0638 (13)	0.0001 (10)	0.0114 (11)	−0.0072 (10)
C5	0.0569 (14)	0.0537 (14)	0.0589 (12)	0.0003 (10)	0.0074 (11)	−0.0005 (10)
C11	0.0672 (16)	0.0619 (14)	0.0677 (14)	0.0116 (11)	0.0020 (12)	0.0019 (11)
C12	0.0634 (16)	0.0448 (12)	0.0722 (14)	0.0048 (10)	0.0118 (12)	0.0090 (10)
C13	0.0617 (14)	0.0437 (12)	0.0635 (13)	−0.0012 (9)	0.0127 (11)	0.0058 (9)
C14	0.0737 (17)	0.0634 (15)	0.0688 (15)	0.0020 (11)	0.0277 (14)	0.0052 (11)
C15	0.091 (2)	0.0772 (17)	0.0579 (14)	−0.0105 (14)	0.0212 (15)	0.0020 (12)
C16	0.085 (2)	0.0819 (18)	0.0649 (15)	−0.0121 (14)	0.0065 (14)	0.0073 (13)
C17	0.0701 (18)	0.111 (2)	0.0691 (16)	0.0171 (15)	0.0029 (14)	0.0011 (14)
C18	0.0739 (18)	0.0830 (18)	0.0619 (14)	0.0169 (13)	0.0112 (13)	−0.0054 (12)
C31	0.0737 (16)	0.0609 (14)	0.0715 (14)	−0.0004 (11)	0.0082 (12)	−0.0152 (11)
C32	0.078	0.059	0.073	−0.0035 (11)	0.0036 (11)	−0.0121 (11)
C32'	0.078	0.059	0.073	−0.0035 (11)	0.0036 (11)	−0.0121 (11)
C33	0.090 (3)	0.067 (4)	0.090 (4)	−0.020 (3)	0.012 (3)	0.005 (3)
C33'	0.085 (4)	0.072 (5)	0.099 (4)	−0.001 (4)	0.003 (4)	−0.006 (4)
C34	0.077 (3)	0.076 (4)	0.097 (4)	−0.012 (2)	0.011 (3)	−0.003 (2)
C34'	0.075 (4)	0.078 (4)	0.103 (5)	−0.005 (4)	−0.004 (4)	0.001 (4)
C35	0.069 (3)	0.082 (4)	0.103 (5)	−0.005 (2)	0.009 (3)	−0.006 (3)
C35'	0.069 (4)	0.079 (5)	0.099 (5)	−0.013 (4)	0.007 (4)	−0.009 (4)
C42	0.0619 (15)	0.0551 (14)	0.0624 (13)	0.0041 (10)	0.0067 (11)	0.0016 (10)
C43	0.0617 (15)	0.0560 (14)	0.0632 (12)	−0.0002 (10)	0.0046 (11)	0.0050 (10)
C44	0.0614 (15)	0.0612 (15)	0.0671 (13)	0.0018 (10)	0.0015 (11)	0.0009 (11)
C45	0.0520 (14)	0.0540 (13)	0.0713 (14)	0.0007 (9)	0.0125 (12)	0.0025 (10)
C46	0.0611 (16)	0.0624 (15)	0.0795 (16)	0.0009 (11)	0.0097 (13)	0.0041 (12)
C47	0.0709 (18)	0.084 (2)	0.0921 (18)	0.0095 (14)	0.0054 (15)	0.0170 (15)
C48	0.077 (2)	0.071 (2)	0.118 (2)	0.0145 (14)	0.0189 (18)	0.0249 (17)
C49	0.080 (2)	0.0561 (16)	0.132 (2)	0.0019 (13)	0.0142 (19)	0.0025 (16)
C50	0.0697 (17)	0.0586 (16)	0.0998 (19)	0.0024 (12)	0.0033 (14)	−0.0030 (13)

O1—C5	1.220 (2)	C32—C33	1.331 (9)
N1—C11	1.433 (3)	C33—C34	1.424 (13)
N2—N1	1.388 (2)	C33—H33	0.9300
N4—N41	1.385 (2)	C33'—C34'	1.424 (15)
N4—C3	1.373 (3)	C33'—H33'	0.9300
N4—C5	1.407 (3)	C34—C35	1.339 (6)
N41—C42	1.278 (3)	C34—H34	0.9300
C3—N2	1.292 (3)	C34'—C35'	1.345 (9)
C5—N1	1.354 (3)	C34'—H34'	0.9300
C11—H11A	0.9700	C35—S1	1.735 (6)
C11—H11B	0.9700	C35—H35	0.9300
C12—O2	1.208 (3)	C35'—S1'	1.744 (10)
C12—C11	1.524 (3)	C35'—H35'	0.9300
C12—C13	1.476 (3)	C42—C43	1.435 (3)
C13—C14	1.394 (3)	C42—H42	0.9300
C13—C18	1.380 (3)	C43—C44	1.323 (3)
C14—C15	1.362 (4)	C43—H43	0.9300
C14—H14	0.9300	C44—H44	0.9300
C15—C16	1.370 (4)	C45—C50	1.388 (3)
C15—H15	0.9300	C45—C46	1.391 (3)
C16—C17	1.378 (3)	C45—C44	1.457 (3)
C16—H16	0.9300	C46—C47	1.371 (3)
C17—H17	0.9300	C46—H46	0.9300
C18—C17	1.369 (4)	C47—C48	1.380 (4)
C18—H18	0.9300	C47—H47	0.9300
C31—C3	1.494 (3)	C48—C49	1.360 (4)
C31—C32	1.491 (4)	C48—H48	0.9300
C31—H31A	0.9700	C49—H49	0.9300
C31—H31B	0.9700	C50—C49	1.378 (4)
C32—S1	1.698 (3)	C50—H50	0.9300
C32—S1—C35	91.9 (3)	H31A—C31—H31B	107.6
N2—N1—C11	122.07 (18)	C31—C32—S1	124.70 (19)
C5—N1—N2	113.51 (18)	C33—C32—S1	109.3 (5)
C5—N1—C11	124.37 (19)	C33—C32—C31	126.0 (6)
C3—N2—N1	104.44 (17)	C32—C33—C34	117.3 (9)
N41—N4—C5	130.25 (17)	C32—C33—H33	121.4
C3—N4—N41	121.59 (19)	C34—C33—H33	121.4
C3—N4—C5	108.14 (18)	C34'—C33'—H33'	122.5
C42—N41—N4	117.04 (18)	C33—C34—H34	125.6
N2—C3—N4	111.7 (2)	C35—C34—C33	108.8 (9)
N2—C3—C31	124.8 (2)	C35—C34—H34	125.6
N4—C3—C31	123.5 (2)	C33'—C34'—H34'	126.2
O1—C5—N1	128.3 (2)	C35'—C34'—C33'	107.5 (13)
O1—C5—N4	129.5 (2)	C35'—C34'—H34'	126.2
N1—C5—N4	102.10 (18)	S1—C35—H35	123.7
N1—C11—C12	112.76 (19)	C34—C35—S1	112.6 (7)
N1—C11—H11A	109.0	C34—C35—H35	123.7
N1—C11—H11B	109.0	S1'—C35'—H35'	123.1
C12—C11—H11A	109.0	C34'—C35'—S1'	113.8 (12)
C12—C11—H11B	109.0	C34'—C35'—H35'	123.1
H11A—C11—H11B	107.8	N41—C42—C43	120.4 (2)
O2—C12—C11	120.3 (2)	N41—C42—H42	119.8
O2—C12—C13	122.3 (2)	C43—C42—H42	119.8
C13—C12—C11	117.41 (19)	C42—C43—H43	119.0
C14—C13—C12	119.5 (2)	C44—C43—C42	122.0 (2)
C18—C13—C14	117.6 (2)	C44—C43—H43	119.0
C18—C13—C12	122.9 (2)	C43—C44—C45	129.4 (2)
C13—C14—H14	119.4	C43—C44—H44	115.3
C15—C14—C13	121.3 (2)	C45—C44—H44	115.3
C15—C14—H14	119.4	C46—C45—C44	122.6 (2)
C14—C15—C16	120.5 (2)	C50—C45—C44	119.5 (2)
C14—C15—H15	119.8	C50—C45—C46	117.9 (2)
C16—C15—H15	119.8	C45—C46—H46	119.7
C15—C16—C17	119.1 (3)	C47—C46—C45	120.5 (2)
C15—C16—H16	120.5	C47—C46—H46	119.7
C17—C16—H16	120.5	C46—C47—C48	120.6 (3)
C16—C17—H17	119.7	C46—C47—H47	119.7
C18—C17—C16	120.7 (3)	C48—C47—H47	119.7
C18—C17—H17	119.7	C47—C48—H48	120.2
C13—C18—H18	119.6	C49—C48—C47	119.7 (3)
C17—C18—C13	120.9 (2)	C49—C48—H48	120.2
C17—C18—H18	119.6	C48—C49—C50	120.2 (3)
C3—C31—H31B	108.6	C48—C49—H49	119.9
C3—C31—H31A	108.6	C50—C49—H49	119.9
C32—C31—C3	114.50 (18)	C45—C50—H50	119.4
C32—C31—H31A	108.6	C49—C50—C45	121.1 (3)
C32—C31—H31B	108.6	C49—C50—H50	119.4
N2—N1—C11—C12	−111.3 (2)	C14—C13—C18—C17	0.8 (4)
C5—N1—C11—C12	71.3 (3)	C13—C14—C15—C16	−0.8 (4)
C3—N2—N1—C5	−0.6 (2)	C14—C15—C16—C17	0.1 (4)
C3—N2—N1—C11	−178.2 (2)	C15—C16—C17—C18	1.0 (4)
N41—N4—C5—O1	−2.8 (4)	C13—C18—C17—C16	−1.5 (4)
N41—N4—C5—N1	179.14 (17)	C32—C31—C3—N2	102.4 (3)
C3—N4—C5—O1	175.3 (2)	C32—C31—C3—N4	−79.4 (3)
C3—N4—C5—N1	−2.8 (2)	C3—C31—C32—S1	101.1 (3)
C3—N4—N41—C42	169.85 (18)	C3—C31—C32—C33	−77.2 (8)
C5—N4—N41—C42	−12.3 (3)	C31—C32—S1—C35	−179.3 (4)
N41—N4—C3—N2	−179.05 (17)	C33—C32—S1—C35	−0.7 (8)
N41—N4—C3—C31	2.5 (3)	S1—C32—C33—C34	1.2 (15)
C5—N4—C3—N2	2.7 (2)	C31—C32—C33—C34	179.7 (9)
C5—N4—C3—C31	−175.77 (19)	C32—C33—C34—C35	−1.1 (17)
N4—N41—C42—C43	−178.75 (17)	C33—C34—C35—S1	0.4 (13)
N4—C3—N2—N1	−1.3 (2)	C33'—C34'—C35'—S1'	−1(2)
C31—C3—N2—N1	177.15 (19)	C34—C35—S1—C32	0.1 (7)
O1—C5—N1—N2	−176.0 (2)	N41—C42—C43—C44	−177.4 (2)
O1—C5—N1—C11	1.6 (4)	C42—C43—C44—C45	−178.5 (2)
N4—C5—N1—N2	2.1 (2)	C46—C45—C44—C43	9.7 (4)
N4—C5—N1—C11	179.67 (19)	C50—C45—C44—C43	−169.5 (2)
O2—C12—C11—N1	11.1 (3)	C44—C45—C46—C47	−178.7 (2)
C13—C12—C11—N1	−167.79 (18)	C50—C45—C46—C47	0.5 (3)
O2—C12—C13—C14	−10.8 (3)	C44—C45—C50—C49	178.9 (2)
O2—C12—C13—C18	171.6 (2)	C46—C45—C50—C49	−0.4 (3)
C11—C12—C13—C14	168.08 (19)	C45—C46—C47—C48	−0.3 (4)
C11—C12—C13—C18	−9.5 (3)	C46—C47—C48—C49	0.0 (4)
C12—C13—C14—C15	−177.4 (2)	C47—C48—C49—C50	0.1 (4)
C18—C13—C14—C15	0.3 (3)	C45—C50—C49—C48	0.1 (4)
C12—C13—C18—C17	178.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C42—H42···O1	0.93	2.23	2.916 (3)	130
C14—H14···Cg1i	0.93	2.91	3.501 (3)	122
C11—H11B···Cg2ii	0.97	2.89	3.816 (3)	159
C48—H48···Cg3iii	0.93	2.79	3.557 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C42—H42⋯O1	0.93	2.23	2.916 (3)	130
C14—H14⋯Cg1i	0.93	2.91	3.501 (3)	122
C11—H11B⋯Cg2ii	0.97	2.89	3.816 (3)	159
C48—H48⋯Cg3iii	0.93	2.79	3.557 (3)	141

Symmetry codes: (i) ; (ii) ; (iii) . Cg1, Cg2 and Cg3 are the centroids of the N1/N2/N4/C3/C5, C13–C18 and S1/C32–C35 rings, respectively.