3-[3-Methyl-4-(3-nitro-benzyl-idene-amino)-5-sulfanyl-idene-4,5-dihydro-1H-1,2,4-triazol-1-yl]-1,3-diphenyl-propan-1-one.

In the title mol-ecule, C(25)H(21)N(5)O(3)S, the triazole ring forms dihedral angles of 21.4 (2), 61.4 (2) and 102.4 (2)° with the nitro-phenyl and two phenyl rings, respectively. In the crystal, weak C-H⋯O hydrogen bonds and π-π inter-actions between the benzene rings from neighbouring mol-ecules [with a centroid-centroid distance of 3.571 (3) Å] consolidate the crystal packing.

Related literature

For the crystal structures of related 1,2,4-triazole-5(4H)-thione derivatives, see: Al-Tamimi et al. (2010 ▶); Fun et al. (2009 ▶); Gao et al. (2011 ▶); Tan et al. (2010 ▶); Wang et al. (2011 ▶); Zhao et al. (2010 ▶).

Experimental

Crystal data

C25H21N5O3S

M = 471.53

Triclinic,

a = 9.0991 (10) Å

b = 11.8026 (15) Å

c = 12.0649 (16) Å

α = 70.92 (1)°

β = 73.042 (12)°

γ = 85.883 (13)°

V = 1170.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 113 K

0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.966, T max = 0.983

15096 measured reflections

5553 independent reflections

3889 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 0.98

5553 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033587/cv5140sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033587/cv5140Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033587/cv5140Isup3.cml

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

C25H21N5O3S	Z = 2
Mr = 471.53	F(000) = 492
Triclinic, P1	Dx = 1.337 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0991 (10) Å	Cell parameters from 4043 reflections
b = 11.8026 (15) Å	θ = 1.8–27.9°
c = 12.0649 (16) Å	µ = 0.18 mm−1
α = 70.92 (1)°	T = 113 K
β = 73.042 (12)°	Prism, colourless
γ = 85.883 (13)°	0.20 × 0.18 × 0.10 mm
V = 1170.9 (3) Å3

Rigaku Saturn CCD area-detector diffractometer	5553 independent reflections
Radiation source: rotating anode	3889 reflections with I > 2σ(I)
multilayer	Rint = 0.031
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 1.8°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −15→15
Tmin = 0.966, Tmax = 0.983	l = −15→15
15096 measured reflections

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: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0481P)2] where P = (Fo2 + 2Fc2)/3
5553 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.17 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
S1	0.02806 (4)	0.24483 (3)	0.15884 (3)	0.02334 (9)
O1	0.13544 (9)	0.55093 (8)	0.09394 (7)	0.0220 (2)
O2	0.60961 (13)	−0.14734 (11)	0.22384 (10)	0.0532 (3)
O3	0.68162 (11)	−0.25204 (9)	0.38191 (9)	0.0387 (3)
N1	−0.10804 (11)	0.39532 (8)	0.28523 (8)	0.0151 (2)
N2	−0.13256 (11)	0.41445 (9)	0.39629 (8)	0.0179 (2)
N3	0.00696 (11)	0.25532 (8)	0.38914 (9)	0.0164 (2)
N4	0.08649 (11)	0.15773 (9)	0.44203 (9)	0.0196 (2)
N5	0.59545 (13)	−0.18126 (11)	0.33417 (11)	0.0313 (3)
C1	−0.02269 (13)	0.29884 (10)	0.27574 (10)	0.0167 (2)
C2	−0.06308 (13)	0.32779 (11)	0.45797 (11)	0.0181 (2)
C3	−0.17203 (13)	0.47954 (10)	0.19116 (10)	0.0157 (2)
H3	−0.1289	0.4604	0.1133	0.019*
C4	−0.12191 (13)	0.60715 (10)	0.16885 (10)	0.0176 (3)
H4A	−0.1706	0.6630	0.1094	0.021*
H4B	−0.1595	0.6258	0.2465	0.021*
C5	0.05068 (13)	0.62844 (11)	0.12070 (10)	0.0177 (3)
C6	0.11439 (14)	0.74641 (11)	0.10917 (10)	0.0204 (3)
C7	0.27293 (16)	0.75992 (13)	0.08526 (12)	0.0291 (3)
H7	0.3383	0.6955	0.0748	0.035*
C8	0.33498 (18)	0.86764 (14)	0.07670 (13)	0.0394 (4)
H8	0.4428	0.8769	0.0607	0.047*
C9	0.23910 (19)	0.96179 (13)	0.09158 (13)	0.0386 (4)
H9	0.2818	1.0358	0.0845	0.046*
C10	0.08236 (18)	0.94858 (12)	0.11653 (12)	0.0326 (3)
H10	0.0174	1.0130	0.1278	0.039*
C11	0.01941 (16)	0.84130 (11)	0.12527 (11)	0.0251 (3)
H11	−0.0886	0.8325	0.1423	0.030*
C12	−0.34582 (13)	0.46533 (10)	0.22760 (10)	0.0164 (2)
C13	−0.43887 (14)	0.49889 (11)	0.32564 (11)	0.0207 (3)
H13	−0.3932	0.5289	0.3723	0.025*
C14	−0.59773 (14)	0.48880 (11)	0.35547 (11)	0.0237 (3)
H14	−0.6601	0.5114	0.4227	0.028*
C15	−0.66556 (14)	0.44607 (12)	0.28775 (11)	0.0255 (3)
H15	−0.7743	0.4401	0.3078	0.031*
C16	−0.57461 (15)	0.41212 (12)	0.19071 (12)	0.0278 (3)
H16	−0.6209	0.3825	0.1442	0.033*
C17	−0.41507 (14)	0.42135 (11)	0.16104 (11)	0.0228 (3)
H17	−0.3531	0.3973	0.0946	0.027*
C18	0.17967 (14)	0.10503 (11)	0.37509 (11)	0.0234 (3)
H18	0.1924	0.1295	0.2895	0.028*
C19	0.26734 (14)	0.00548 (11)	0.43263 (11)	0.0208 (3)
C20	0.38127 (14)	−0.04456 (12)	0.35914 (12)	0.0244 (3)
H20	0.3982	−0.0181	0.2730	0.029*
C21	0.46964 (14)	−0.13341 (11)	0.41314 (12)	0.0229 (3)
C22	0.44816 (14)	−0.17667 (11)	0.53782 (12)	0.0236 (3)
H22	0.5108	−0.2379	0.5724	0.028*
C23	0.33234 (15)	−0.12806 (11)	0.61123 (12)	0.0249 (3)
H23	0.3142	−0.1568	0.6975	0.030*
C24	0.24284 (14)	−0.03785 (11)	0.55959 (11)	0.0228 (3)
H24	0.1641	−0.0051	0.6108	0.027*
C25	−0.05494 (15)	0.30789 (12)	0.58367 (11)	0.0268 (3)
H25A	−0.1045	0.3738	0.6121	0.040*
H25B	0.0529	0.3048	0.5838	0.040*
H25C	−0.1078	0.2319	0.6383	0.040*

	U11	U22	U33	U12	U13	U23
S1	0.03061 (18)	0.02282 (18)	0.02119 (17)	0.01031 (13)	−0.01063 (14)	−0.01219 (14)
O1	0.0183 (4)	0.0238 (5)	0.0240 (5)	0.0038 (3)	−0.0054 (4)	−0.0089 (4)
O2	0.0497 (7)	0.0763 (9)	0.0373 (6)	0.0366 (6)	−0.0175 (5)	−0.0258 (6)
O3	0.0318 (6)	0.0383 (6)	0.0484 (6)	0.0215 (5)	−0.0167 (5)	−0.0164 (5)
N1	0.0162 (5)	0.0169 (5)	0.0133 (5)	0.0032 (4)	−0.0047 (4)	−0.0063 (4)
N2	0.0187 (5)	0.0214 (5)	0.0154 (5)	0.0043 (4)	−0.0063 (4)	−0.0078 (4)
N3	0.0170 (5)	0.0156 (5)	0.0175 (5)	0.0048 (4)	−0.0072 (4)	−0.0053 (4)
N4	0.0190 (5)	0.0164 (5)	0.0241 (5)	0.0052 (4)	−0.0110 (4)	−0.0040 (4)
N5	0.0257 (6)	0.0334 (7)	0.0388 (7)	0.0122 (5)	−0.0128 (5)	−0.0160 (6)
C1	0.0159 (6)	0.0157 (6)	0.0179 (6)	0.0013 (4)	−0.0055 (5)	−0.0043 (5)
C2	0.0160 (6)	0.0206 (6)	0.0186 (6)	0.0029 (5)	−0.0051 (5)	−0.0078 (5)
C3	0.0162 (6)	0.0178 (6)	0.0137 (6)	0.0040 (4)	−0.0059 (5)	−0.0049 (5)
C4	0.0182 (6)	0.0174 (6)	0.0163 (6)	0.0040 (5)	−0.0047 (5)	−0.0052 (5)
C5	0.0201 (6)	0.0204 (6)	0.0124 (6)	0.0014 (5)	−0.0062 (5)	−0.0035 (5)
C6	0.0259 (7)	0.0223 (6)	0.0132 (6)	−0.0024 (5)	−0.0068 (5)	−0.0043 (5)
C7	0.0267 (7)	0.0344 (8)	0.0279 (7)	−0.0040 (6)	−0.0062 (6)	−0.0125 (6)
C8	0.0338 (8)	0.0462 (10)	0.0393 (9)	−0.0160 (7)	−0.0080 (7)	−0.0136 (7)
C9	0.0554 (10)	0.0269 (8)	0.0357 (8)	−0.0141 (7)	−0.0163 (7)	−0.0070 (7)
C10	0.0503 (9)	0.0218 (7)	0.0277 (7)	−0.0012 (6)	−0.0167 (7)	−0.0052 (6)
C11	0.0330 (7)	0.0209 (7)	0.0220 (7)	0.0007 (5)	−0.0110 (6)	−0.0050 (5)
C12	0.0165 (6)	0.0144 (6)	0.0172 (6)	0.0031 (4)	−0.0065 (5)	−0.0025 (5)
C13	0.0198 (6)	0.0227 (6)	0.0212 (6)	0.0040 (5)	−0.0075 (5)	−0.0082 (5)
C14	0.0192 (6)	0.0260 (7)	0.0223 (7)	0.0061 (5)	−0.0034 (5)	−0.0063 (6)
C15	0.0155 (6)	0.0282 (7)	0.0287 (7)	0.0017 (5)	−0.0071 (5)	−0.0033 (6)
C16	0.0244 (7)	0.0333 (8)	0.0301 (7)	−0.0019 (6)	−0.0128 (6)	−0.0111 (6)
C17	0.0220 (6)	0.0259 (7)	0.0221 (6)	0.0015 (5)	−0.0068 (5)	−0.0096 (6)
C18	0.0233 (7)	0.0250 (7)	0.0223 (7)	0.0071 (5)	−0.0092 (5)	−0.0072 (6)
C19	0.0194 (6)	0.0179 (6)	0.0273 (7)	0.0037 (5)	−0.0103 (5)	−0.0076 (5)
C20	0.0231 (7)	0.0271 (7)	0.0259 (7)	0.0067 (5)	−0.0108 (5)	−0.0103 (6)
C21	0.0195 (6)	0.0205 (6)	0.0320 (7)	0.0049 (5)	−0.0091 (5)	−0.0122 (6)
C22	0.0201 (6)	0.0161 (6)	0.0346 (7)	0.0027 (5)	−0.0125 (5)	−0.0044 (6)
C23	0.0241 (7)	0.0216 (7)	0.0256 (7)	0.0006 (5)	−0.0086 (5)	−0.0019 (6)
C24	0.0205 (6)	0.0202 (6)	0.0273 (7)	0.0029 (5)	−0.0071 (5)	−0.0076 (6)
C25	0.0315 (7)	0.0312 (7)	0.0220 (7)	0.0127 (6)	−0.0133 (6)	−0.0117 (6)

S1—C1	1.6656 (12)	C10—C11	1.3870 (18)
O1—C5	1.2176 (14)	C10—H10	0.9500
O2—N5	1.2278 (14)	C11—H11	0.9500
O3—N5	1.2244 (14)	C12—C17	1.3878 (17)
N1—C1	1.3488 (14)	C12—C13	1.3952 (16)
N1—N2	1.3828 (12)	C13—C14	1.3880 (17)
N1—C3	1.4765 (14)	C13—H13	0.9500
N2—C2	1.2975 (15)	C14—C15	1.3824 (18)
N3—C2	1.3802 (14)	C14—H14	0.9500
N3—N4	1.3881 (13)	C15—C16	1.3820 (17)
N3—C1	1.3944 (14)	C15—H15	0.9500
N4—C18	1.2694 (14)	C16—C17	1.3933 (17)
N5—C21	1.4697 (16)	C16—H16	0.9500
C2—C25	1.4801 (16)	C17—H17	0.9500
C3—C12	1.5187 (15)	C18—C19	1.4676 (16)
C3—C4	1.5202 (16)	C18—H18	0.9500
C3—H3	1.0000	C19—C20	1.3884 (17)
C4—C5	1.5152 (15)	C19—C24	1.4010 (17)
C4—H4A	0.9900	C20—C21	1.3815 (17)
C4—H4B	0.9900	C20—H20	0.9500
C5—C6	1.4955 (17)	C21—C22	1.3793 (17)
C6—C11	1.3944 (17)	C22—C23	1.3875 (17)
C6—C7	1.3963 (17)	C22—H22	0.9500
C7—C8	1.3890 (19)	C23—C24	1.3866 (17)
C7—H7	0.9500	C23—H23	0.9500
C8—C9	1.388 (2)	C24—H24	0.9500
C8—H8	0.9500	C25—H25A	0.9800
C9—C10	1.378 (2)	C25—H25B	0.9800
C9—H9	0.9500	C25—H25C	0.9800
C1—N1—N2	113.68 (9)	C10—C11—H11	119.9
C1—N1—C3	127.18 (10)	C6—C11—H11	119.9
N2—N1—C3	119.13 (9)	C17—C12—C13	118.78 (11)
C2—N2—N1	104.77 (9)	C17—C12—C3	120.07 (10)
C2—N3—N4	117.92 (9)	C13—C12—C3	121.13 (10)
C2—N3—C1	108.76 (9)	C14—C13—C12	120.45 (12)
N4—N3—C1	133.31 (9)	C14—C13—H13	119.8
C18—N4—N3	119.73 (10)	C12—C13—H13	119.8
O3—N5—O2	123.47 (11)	C15—C14—C13	120.29 (12)
O3—N5—C21	118.13 (11)	C15—C14—H14	119.9
O2—N5—C21	118.39 (11)	C13—C14—H14	119.9
N1—C1—N3	102.22 (9)	C16—C15—C14	119.79 (12)
N1—C1—S1	128.11 (9)	C16—C15—H15	120.1
N3—C1—S1	129.64 (9)	C14—C15—H15	120.1
N2—C2—N3	110.56 (10)	C15—C16—C17	120.06 (12)
N2—C2—C25	126.08 (11)	C15—C16—H16	120.0
N3—C2—C25	123.34 (10)	C17—C16—H16	120.0
N1—C3—C12	110.99 (9)	C12—C17—C16	120.62 (12)
N1—C3—C4	109.66 (9)	C12—C17—H17	119.7
C12—C3—C4	111.73 (9)	C16—C17—H17	119.7
N1—C3—H3	108.1	N4—C18—C19	118.61 (11)
C12—C3—H3	108.1	N4—C18—H18	120.7
C4—C3—H3	108.1	C19—C18—H18	120.7
C5—C4—C3	113.55 (10)	C20—C19—C24	118.98 (11)
C5—C4—H4A	108.9	C20—C19—C18	119.20 (11)
C3—C4—H4A	108.9	C24—C19—C18	121.78 (11)
C5—C4—H4B	108.9	C21—C20—C19	119.02 (12)
C3—C4—H4B	108.9	C21—C20—H20	120.5
H4A—C4—H4B	107.7	C19—C20—H20	120.5
O1—C5—C6	120.86 (11)	C22—C21—C20	122.89 (11)
O1—C5—C4	120.93 (11)	C22—C21—N5	118.42 (11)
C6—C5—C4	118.20 (10)	C20—C21—N5	118.66 (11)
C11—C6—C7	119.51 (12)	C21—C22—C23	117.96 (11)
C11—C6—C5	121.74 (11)	C21—C22—H22	121.0
C7—C6—C5	118.72 (11)	C23—C22—H22	121.0
C8—C7—C6	119.97 (14)	C24—C23—C22	120.48 (12)
C8—C7—H7	120.0	C24—C23—H23	119.8
C6—C7—H7	120.0	C22—C23—H23	119.8
C9—C8—C7	119.85 (14)	C23—C24—C19	120.66 (11)
C9—C8—H8	120.1	C23—C24—H24	119.7
C7—C8—H8	120.1	C19—C24—H24	119.7
C10—C9—C8	120.45 (13)	C2—C25—H25A	109.5
C10—C9—H9	119.8	C2—C25—H25B	109.5
C8—C9—H9	119.8	H25A—C25—H25B	109.5
C9—C10—C11	120.07 (14)	C2—C25—H25C	109.5
C9—C10—H10	120.0	H25A—C25—H25C	109.5
C11—C10—H10	120.0	H25B—C25—H25C	109.5
C10—C11—C6	120.13 (13)
C1—N1—N2—C2	−0.75 (13)	C8—C9—C10—C11	−0.9 (2)
C3—N1—N2—C2	−179.67 (10)	C9—C10—C11—C6	0.17 (19)
C2—N3—N4—C18	−164.43 (11)	C7—C6—C11—C10	0.54 (18)
C1—N3—N4—C18	16.93 (19)	C5—C6—C11—C10	178.58 (11)
N2—N1—C1—N3	0.20 (12)	N1—C3—C12—C17	−113.03 (12)
C3—N1—C1—N3	179.01 (10)	C4—C3—C12—C17	124.22 (12)
N2—N1—C1—S1	178.48 (9)	N1—C3—C12—C13	68.72 (13)
C3—N1—C1—S1	−2.70 (18)	C4—C3—C12—C13	−54.02 (14)
C2—N3—C1—N1	0.41 (12)	C17—C12—C13—C14	−0.26 (17)
N4—N3—C1—N1	179.13 (11)	C3—C12—C13—C14	178.01 (10)
C2—N3—C1—S1	−177.84 (10)	C12—C13—C14—C15	−0.43 (18)
N4—N3—C1—S1	0.88 (19)	C13—C14—C15—C16	0.66 (19)
N1—N2—C2—N3	0.99 (13)	C14—C15—C16—C17	−0.21 (19)
N1—N2—C2—C25	179.86 (11)	C13—C12—C17—C16	0.71 (18)
N4—N3—C2—N2	−179.87 (10)	C3—C12—C17—C16	−177.57 (11)
C1—N3—C2—N2	−0.92 (13)	C15—C16—C17—C12	−0.48 (19)
N4—N3—C2—C25	1.22 (17)	N3—N4—C18—C19	177.32 (10)
C1—N3—C2—C25	−179.83 (11)	N4—C18—C19—C20	−173.19 (12)
C1—N1—C3—C12	110.32 (12)	N4—C18—C19—C24	4.59 (18)
N2—N1—C3—C12	−70.93 (12)	C24—C19—C20—C21	−1.64 (19)
C1—N1—C3—C4	−125.75 (12)	C18—C19—C20—C21	176.20 (12)
N2—N1—C3—C4	53.00 (13)	C19—C20—C21—C22	1.2 (2)
N1—C3—C4—C5	61.96 (12)	C19—C20—C21—N5	−176.71 (11)
C12—C3—C4—C5	−174.54 (9)	O3—N5—C21—C22	−4.44 (18)
C3—C4—C5—O1	5.85 (15)	O2—N5—C21—C22	176.29 (13)
C3—C4—C5—C6	−173.01 (9)	O3—N5—C21—C20	173.56 (12)
O1—C5—C6—C11	172.26 (11)	O2—N5—C21—C20	−5.71 (19)
C4—C5—C6—C11	−8.89 (16)	C20—C21—C22—C23	0.00 (19)
O1—C5—C6—C7	−9.69 (17)	N5—C21—C22—C23	177.90 (11)
C4—C5—C6—C7	169.17 (10)	C21—C22—C23—C24	−0.70 (19)
C11—C6—C7—C8	−0.52 (19)	C22—C23—C24—C19	0.22 (19)
C5—C6—C7—C8	−178.62 (11)	C20—C19—C24—C23	0.97 (18)
C6—C7—C8—C9	−0.2 (2)	C18—C19—C24—C23	−176.82 (12)
C7—C8—C9—C10	0.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	1.00	2.57	3.4922 (15)	154
C4—H4B···O3ii	0.99	2.59	3.5002 (16)	153
C17—H17···O1i	0.95	2.47	3.3076 (15)	147
C25—H25B···O3iii	0.98	2.57	3.5310 (18)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	1.00	2.57	3.4922 (15)	154
C4—H4B⋯O3ii	0.99	2.59	3.5002 (16)	153
C17—H17⋯O1i	0.95	2.47	3.3076 (15)	147
C25—H25B⋯O3iii	0.98	2.57	3.5310 (18)	168

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