3-[3-Methyl-4-(3-nitro­benzyl­idene­amino)-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-1-yl]-1,3-diphenyl­propan-1-one

Gao, Y.; Dong, Y.

doi:10.1107/S1600536811033587

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2482

doi:10.1107/S1600536811033587

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3-[3-Methyl-4-(3-nitrobenzylideneamino)-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl]-1,3-diphenylpropan-1-one

Yan Gao ^a and Yan Dong ^a ^*

^aSchool of Chemical Engineering, University of Science and Technology LiaoNing, Anshan, 114051, People's Republic of China
^*Correspondence e-mail: zhao_submit@yahoo.com.cn

(Received 21 July 2011; accepted 18 August 2011; online 27 August 2011)

In the title molecule, C₂₅H₂₁N₅O₃S, the triazole ring forms dihedral angles of 21.4 (2), 61.4 (2) and 102.4 (2)° with the nitrophenyl and two phenyl rings, respectively. In the crystal, weak C—H⋯O hydrogen bonds and π–π interactions between the benzene rings from neighbouring molecules [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_r = 471.53
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.090
S = 0.98
5553 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) -x, -y+1, -z; (ii) x-1, y+1, z; (iii) -x+1, -y, -z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033587/cv5140sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811033587/cv5140Isup3.cml

checkCIF report

Comment top

In continuation of structural study of Mannich bases derivatives synthesized by reactions of the amino heterocycles and aromatic aldehydes in our group (Wang et al., 2011), we present here the crystal structure of the title compound, (I).

The bond lengths and angles in (I) (Fig. 1) are normal and comparable with those reported for the related 1,2,4-triazole- 5(4H)-thione derivatives (Al-Tamimi et al., 2010; Fun et al. (2009); Tan et al. (2010); Wang et al., 2011;). The C1 and C2 atoms in the 1,2,4-triazole ring show distorted C_sp² hybridization states with the bond angles of 102.22 (9)° (N1—C1—N3), 129.64 (9)° (N3—C1—S1), 110.56 (10)° (N2—C2—N3) and 126.08 (11) ° (N2—C2—C25), which are in a good agreement with the literature (Zhao et al., 2010; Gao et al., 2011). The 1,2,4-triazole ring makes the dihedral angles of 102.4 (2), 61.4 (2) and 21.4 (2)° with phenyl rings (C6—C11 and C12—C17) and nitrophenyl ring (C19—C24), respectively.

In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) and π—π interactions between the benzene rings from the neighbouring molecules with the centroid-centroid distance of 3.571 (3) Å consolidate the crystal packing.

Related literature top

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 top

The title compound was synthesized by the reaction of 3-nitrobenzaldehyde (2.0 mmol) and 3-(4-amino-3-methyl-5-thioxo-4,5- dihydro-1H-1,2,4-triazol-1-yl)-1,3-diphenylpropan-1-one(2.0 mmol) by refluxing in ethnol. The reaction progress was monitored via TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the target product as colourless solid in 75% yield. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 (Sheldrick, 2008).

Figures top

Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 55% probability level.

3-[3-Methyl-4-(3-nitrobenzylideneamino)-5-sulfanylidene-4,5-dihydro-1H- 1,2,4-triazol-1-yl]-1,3-diphenylpropan-1-one top

Crystal data top

C₂₅H₂₁N₅O₃S	Z = 2
M_r = 471.53	F(000) = 492
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0481P)²] where P = (F_o² + 2F_c²)/3
5553 reflections	(Δ/σ)_max < 0.001
308 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₅H₂₁N₅O₃S	γ = 85.883 (13)°
M_r = 471.53	V = 1170.9 (3) Å³
Triclinic, P1	Z = 2
a = 9.0991 (10) Å	Mo Kα radiation
b = 11.8026 (15) Å	µ = 0.18 mm⁻¹
c = 12.0649 (16) Å	T = 113 K
α = 70.92 (1)°	0.20 × 0.18 × 0.10 mm
β = 73.042 (12)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5553 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3889 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.983	R_int = 0.031
15096 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 0.98	Δρ_max = 0.40 e Å⁻³
5553 reflections	Δρ_min = −0.17 e Å⁻³
308 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₂₅H₂₁N₅O₃S
M_r	471.53
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	9.0991 (10), 11.8026 (15), 12.0649 (16)
α, β, γ (°)	70.92 (1), 73.042 (12), 85.883 (13)
V (Å³)	1170.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.20 × 0.18 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.966, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	15096, 5553, 3889
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.090, 0.98
No. of reflections	5553
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.17

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

References

Al-Tamimi, A.-M. S., Bari, A., Al-Omar, M. A., Alrashood, K. A. & El-Emam, A. A. (2010). Acta Cryst. E66, o1756. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Chantrapromma, S., Sujith, K. V. & Kalluraya, B. (2009). Acta Cryst. E65, o495–o496. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gao, Y., Zhang, L. & Wang, H. (2011). Acta Cryst. E67, o1794. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tan, K. W., Maah, M. J. & Ng, S. W. (2010). Acta Cryst. E66, o2224. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, W., Gao, Y., Xiao, Z., Yao, H. & Zhang, J. (2011). Acta Cryst. E67, o269. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhao, B., Liu, Z., Gao, Y., Song, B. & Deng, Q. (2010). Acta Cryst. E66, o2814. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 9| September 2011| Page o2482

doi:10.1107/S1600536811033587

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

3-[3-Methyl-4-(3-nitro­benzyl­­idene­amino)-5-sulfanyl­­idene-4,5-di­hydro-1H-1,2,4-triazol-1-yl]-1,3-di­phenyl­propan-1-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

3-[3-Methyl-4-(3-nitrobenzylideneamino)-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl]-1,3-diphenylpropan-1-one