4-Amino-1-(2-benzoyl-1-phenyl-eth-yl)-3-phenyl-1H-1,2,4-triazol-5(4H)-thione.

In the title compound, C(23)H(20)N(4)OS, the two phenyl rings of the diphenyl-propanone fragment form a dihedral angle of 86.8 (1)°, and the third phenyl ring attached to the triazole ring is twisted from the latter at 40.1 (1)°. In the crystal, mol-ecules are paired into centrosymmetric dimers via pairs of inter-molecular N-H⋯O and N-H⋯S hydrogen bonds.

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 ▶); Tan et al. (2010 ▶); Wang et al. (2011 ▶).

Experimental

Crystal data

C23H20N4OS

M = 400.49

Triclinic,

a = 9.4625 (19) Å

b = 11.340 (2) Å

c = 11.655 (2) Å

α = 111.80 (3)°

β = 111.01 (3)°

γ = 98.91 (3)°

V = 1022.4 (4) 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 = 0.965, T max = 0.982

9308 measured reflections

3590 independent reflections

2686 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.121

S = 1.04

3590 reflections

271 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.29 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810054553/cv5022sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054553/cv5022Isup2.hkl

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

C23H20N4OS	Z = 2
Mr = 400.49	F(000) = 420
Triclinic, P1	Dx = 1.301 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4625 (19) Å	Cell parameters from 3363 reflections
b = 11.340 (2) Å	θ = 2.1–27.8°
c = 11.655 (2) Å	µ = 0.18 mm−1
α = 111.80 (3)°	T = 113 K
β = 111.01 (3)°	Prism, colourless
γ = 98.91 (3)°	0.20 × 0.18 × 0.10 mm
V = 1022.4 (4) Å3

Rigaku Saturn CCD area-detector diffractometer	3590 independent reflections
Radiation source: rotating anode	2686 reflections with I > 2σ(I)
multilayer	Rint = 0.039
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 2.1°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −13→13
Tmin = 0.965, Tmax = 0.982	l = −13→12
9308 measured reflections

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.071P)2 + 0.1941P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3590 reflections	Δρmax = 0.35 e Å−3
271 parameters	Δρmin = −0.29 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.107 (8)

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	0.54562 (6)	−0.11721 (5)	0.13685 (5)	0.02158 (19)
O1	0.45937 (17)	0.25822 (14)	0.24735 (14)	0.0237 (4)
N1	0.82240 (19)	0.25821 (16)	0.32190 (16)	0.0182 (4)
N2	0.72008 (19)	0.15086 (16)	0.31246 (16)	0.0163 (4)
N3	0.75632 (19)	0.07328 (15)	0.13230 (15)	0.0159 (4)
N4	0.7447 (2)	−0.01242 (17)	0.00269 (17)	0.0213 (4)
H4A	0.703 (2)	−0.0962 (13)	−0.010 (2)	0.036 (7)*
H4B	0.675 (2)	0.005 (2)	−0.062 (2)	0.055 (9)*
C1	0.9302 (2)	0.4216 (2)	0.2059 (2)	0.0231 (5)
H1	0.8614	0.4514	0.2443	0.028*
C2	1.0231 (3)	0.5072 (2)	0.1812 (2)	0.0252 (5)
H2	1.0168	0.5949	0.2010	0.030*
C3	1.1260 (2)	0.4637 (2)	0.1269 (2)	0.0257 (5)
H3	1.1913	0.5223	0.1111	0.031*
C4	1.1330 (3)	0.3347 (2)	0.0962 (2)	0.0260 (5)
H4	1.2038	0.3059	0.0600	0.031*
C5	1.0376 (2)	0.2475 (2)	0.1179 (2)	0.0221 (5)
H5	1.0408	0.1586	0.0943	0.026*
C6	0.9371 (2)	0.2915 (2)	0.17470 (19)	0.0176 (4)
C7	0.8422 (2)	0.20849 (19)	0.21041 (19)	0.0176 (5)
C8	0.6737 (2)	0.03559 (19)	0.19571 (19)	0.0160 (4)
C9	0.6600 (2)	0.17172 (19)	0.41591 (19)	0.0178 (5)
H9	0.5473	0.1088	0.3687	0.021*
C10	0.7610 (2)	0.14453 (18)	0.53269 (19)	0.0176 (4)
C11	0.9151 (2)	0.1418 (2)	0.5597 (2)	0.0222 (5)
H11	0.9606	0.1555	0.5032	0.027*
C12	1.0040 (3)	0.1191 (2)	0.6688 (2)	0.0245 (5)
H12	1.1093	0.1169	0.6861	0.029*
C13	0.9392 (3)	0.0995 (2)	0.7523 (2)	0.0237 (5)
H13	0.9991	0.0824	0.8259	0.028*
C14	0.7863 (3)	0.1051 (2)	0.7281 (2)	0.0250 (5)
H14	0.7426	0.0939	0.7866	0.030*
C15	0.6970 (2)	0.1268 (2)	0.6188 (2)	0.0215 (5)
H15	0.5921	0.1297	0.6023	0.026*
C16	0.6580 (2)	0.31677 (19)	0.47288 (19)	0.0187 (5)
H16A	0.6083	0.3303	0.5364	0.022*
H16B	0.7697	0.3799	0.5269	0.022*
C17	0.5659 (2)	0.3486 (2)	0.35832 (19)	0.0174 (4)
C18	0.6095 (2)	0.4905 (2)	0.3827 (2)	0.0188 (5)
C19	0.6976 (2)	0.5982 (2)	0.5161 (2)	0.0229 (5)
H19	0.7328	0.5816	0.5941	0.028*
C20	0.7336 (3)	0.7291 (2)	0.5348 (2)	0.0278 (5)
H20	0.7929	0.8020	0.6258	0.033*
C21	0.6842 (3)	0.7544 (2)	0.4223 (3)	0.0298 (6)
H21	0.7084	0.8445	0.4361	0.036*
C22	0.5990 (3)	0.6483 (2)	0.2889 (2)	0.0317 (6)
H22	0.5672	0.6657	0.2114	0.038*
C23	0.5603 (3)	0.5168 (2)	0.2688 (2)	0.0261 (5)
H23	0.5003	0.4443	0.1775	0.031*

	U11	U22	U33	U12	U13	U23
S1	0.0236 (3)	0.0133 (3)	0.0240 (3)	0.0040 (2)	0.0089 (2)	0.0076 (2)
O1	0.0232 (8)	0.0199 (8)	0.0169 (7)	0.0047 (6)	0.0019 (6)	0.0057 (6)
N1	0.0185 (9)	0.0149 (9)	0.0190 (9)	0.0036 (7)	0.0084 (7)	0.0066 (7)
N2	0.0188 (9)	0.0134 (8)	0.0154 (8)	0.0037 (7)	0.0078 (7)	0.0061 (7)
N3	0.0171 (9)	0.0136 (8)	0.0144 (8)	0.0062 (7)	0.0056 (7)	0.0049 (7)
N4	0.0235 (10)	0.0178 (9)	0.0152 (9)	0.0066 (8)	0.0075 (8)	0.0017 (7)
C1	0.0231 (11)	0.0187 (11)	0.0211 (11)	0.0038 (9)	0.0079 (9)	0.0061 (9)
C2	0.0282 (12)	0.0217 (11)	0.0192 (11)	0.0033 (10)	0.0051 (10)	0.0106 (9)
C3	0.0215 (11)	0.0267 (12)	0.0212 (11)	−0.0007 (9)	0.0052 (9)	0.0114 (9)
C4	0.0206 (11)	0.0295 (12)	0.0226 (11)	0.0032 (10)	0.0104 (10)	0.0084 (10)
C5	0.0217 (11)	0.0198 (11)	0.0170 (10)	0.0039 (9)	0.0057 (9)	0.0052 (9)
C6	0.0154 (10)	0.0195 (10)	0.0105 (9)	0.0006 (8)	0.0029 (8)	0.0049 (8)
C7	0.0161 (10)	0.0146 (10)	0.0158 (10)	0.0026 (8)	0.0045 (8)	0.0046 (8)
C8	0.0166 (10)	0.0142 (10)	0.0161 (10)	0.0064 (8)	0.0057 (9)	0.0070 (8)
C9	0.0185 (10)	0.0168 (10)	0.0156 (10)	0.0038 (8)	0.0075 (9)	0.0062 (8)
C10	0.0200 (10)	0.0105 (9)	0.0166 (10)	0.0027 (8)	0.0068 (9)	0.0032 (8)
C11	0.0235 (11)	0.0216 (11)	0.0215 (11)	0.0076 (9)	0.0106 (9)	0.0096 (9)
C12	0.0238 (11)	0.0226 (11)	0.0225 (11)	0.0090 (9)	0.0078 (10)	0.0080 (9)
C13	0.0308 (12)	0.0195 (11)	0.0153 (10)	0.0067 (9)	0.0053 (10)	0.0082 (9)
C14	0.0314 (12)	0.0247 (11)	0.0183 (11)	0.0041 (10)	0.0130 (10)	0.0098 (9)
C15	0.0206 (11)	0.0191 (10)	0.0216 (11)	0.0032 (9)	0.0090 (9)	0.0081 (9)
C16	0.0213 (10)	0.0152 (10)	0.0158 (10)	0.0036 (8)	0.0079 (9)	0.0048 (8)
C17	0.0177 (10)	0.0196 (10)	0.0142 (10)	0.0065 (9)	0.0074 (9)	0.0069 (8)
C18	0.0143 (10)	0.0194 (11)	0.0241 (11)	0.0062 (8)	0.0097 (9)	0.0103 (9)
C19	0.0196 (11)	0.0195 (11)	0.0253 (11)	0.0043 (9)	0.0094 (9)	0.0077 (9)
C20	0.0234 (11)	0.0180 (11)	0.0388 (13)	0.0067 (9)	0.0149 (10)	0.0094 (10)
C21	0.0252 (12)	0.0222 (12)	0.0519 (15)	0.0120 (10)	0.0196 (11)	0.0232 (11)
C22	0.0323 (13)	0.0343 (13)	0.0386 (13)	0.0124 (11)	0.0151 (11)	0.0273 (11)
C23	0.0238 (11)	0.0267 (12)	0.0271 (12)	0.0071 (10)	0.0089 (10)	0.0149 (10)

S1—C8	1.677 (2)	C10—C11	1.386 (3)
O1—C17	1.225 (2)	C10—C15	1.400 (3)
N1—C7	1.305 (3)	C11—C12	1.391 (3)
N1—N2	1.375 (2)	C11—H11	0.9500
N2—C8	1.351 (2)	C12—C13	1.385 (3)
N2—C9	1.468 (3)	C12—H12	0.9500
N3—C8	1.373 (3)	C13—C14	1.387 (3)
N3—C7	1.374 (3)	C13—H13	0.9500
N3—N4	1.413 (2)	C14—C15	1.387 (3)
N4—H4A	0.91 (2)	C14—H14	0.9500
N4—H4B	0.91 (2)	C15—H15	0.9500
C1—C2	1.387 (3)	C16—C17	1.514 (3)
C1—C6	1.400 (3)	C16—H16A	0.9900
C1—H1	0.9500	C16—H16B	0.9900
C2—C3	1.396 (3)	C17—C18	1.488 (3)
C2—H2	0.9500	C18—C19	1.396 (3)
C3—C4	1.389 (3)	C18—C23	1.400 (3)
C3—H3	0.9500	C19—C20	1.385 (3)
C4—C5	1.389 (3)	C19—H19	0.9500
C4—H4	0.9500	C20—C21	1.379 (3)
C5—C6	1.395 (3)	C20—H20	0.9500
C5—H5	0.9500	C21—C22	1.388 (3)
C6—C7	1.471 (3)	C21—H21	0.9500
C9—C10	1.527 (3)	C22—C23	1.386 (3)
C9—C16	1.534 (3)	C22—H22	0.9500
C9—H9	1.0000	C23—H23	0.9500
C7—N1—N2	104.69 (16)	C10—C11—C12	120.6 (2)
C8—N2—N1	113.11 (16)	C10—C11—H11	119.7
C8—N2—C9	126.58 (17)	C12—C11—H11	119.7
N1—N2—C9	120.00 (15)	C13—C12—C11	120.2 (2)
C8—N3—C7	109.01 (16)	C13—C12—H12	119.9
C8—N3—N4	124.81 (16)	C11—C12—H12	119.9
C7—N3—N4	126.05 (17)	C12—C13—C14	119.66 (19)
N3—N4—H4A	104.0 (15)	C12—C13—H13	120.2
N3—N4—H4B	106.7 (17)	C14—C13—H13	120.2
H4A—N4—H4B	111.0 (14)	C15—C14—C13	120.3 (2)
C2—C1—C6	120.4 (2)	C15—C14—H14	119.9
C2—C1—H1	119.8	C13—C14—H14	119.9
C6—C1—H1	119.8	C14—C15—C10	120.3 (2)
C1—C2—C3	119.5 (2)	C14—C15—H15	119.9
C1—C2—H2	120.2	C10—C15—H15	119.9
C3—C2—H2	120.2	C17—C16—C9	112.01 (16)
C4—C3—C2	120.0 (2)	C17—C16—H16A	109.2
C4—C3—H3	120.0	C9—C16—H16A	109.2
C2—C3—H3	120.0	C17—C16—H16B	109.2
C3—C4—C5	120.7 (2)	C9—C16—H16B	109.2
C3—C4—H4	119.6	H16A—C16—H16B	107.9
C5—C4—H4	119.6	O1—C17—C18	121.08 (18)
C4—C5—C6	119.5 (2)	O1—C17—C16	120.19 (18)
C4—C5—H5	120.3	C18—C17—C16	118.73 (17)
C6—C5—H5	120.3	C19—C18—C23	119.19 (19)
C5—C6—C1	119.83 (19)	C19—C18—C17	121.70 (18)
C5—C6—C7	122.41 (19)	C23—C18—C17	119.11 (18)
C1—C6—C7	117.70 (18)	C20—C19—C18	120.1 (2)
N1—C7—N3	110.27 (18)	C20—C19—H19	120.0
N1—C7—C6	122.88 (17)	C18—C19—H19	120.0
N3—C7—C6	126.76 (17)	C21—C20—C19	120.5 (2)
N2—C8—N3	102.87 (16)	C21—C20—H20	119.7
N2—C8—S1	130.11 (16)	C19—C20—H20	119.7
N3—C8—S1	127.01 (14)	C20—C21—C22	120.1 (2)
N2—C9—C10	112.15 (16)	C20—C21—H21	120.0
N2—C9—C16	107.96 (16)	C22—C21—H21	120.0
C10—C9—C16	111.00 (16)	C23—C22—C21	120.0 (2)
N2—C9—H9	108.6	C23—C22—H22	120.0
C10—C9—H9	108.6	C21—C22—H22	120.0
C16—C9—H9	108.6	C22—C23—C18	120.2 (2)
C11—C10—C15	118.93 (18)	C22—C23—H23	119.9
C11—C10—C9	122.58 (18)	C18—C23—H23	119.9
C15—C10—C9	118.44 (18)
C7—N1—N2—C8	−1.1 (2)	C8—N2—C9—C16	−145.64 (18)
C7—N1—N2—C9	−175.02 (17)	N1—N2—C9—C16	27.4 (2)
C6—C1—C2—C3	−1.1 (3)	N2—C9—C10—C11	18.4 (3)
C1—C2—C3—C4	1.0 (3)	C16—C9—C10—C11	−102.5 (2)
C2—C3—C4—C5	0.4 (3)	N2—C9—C10—C15	−164.09 (17)
C3—C4—C5—C6	−1.8 (3)	C16—C9—C10—C15	75.1 (2)
C4—C5—C6—C1	1.6 (3)	C15—C10—C11—C12	1.3 (3)
C4—C5—C6—C7	−175.21 (18)	C9—C10—C11—C12	178.81 (18)
C2—C1—C6—C5	−0.2 (3)	C10—C11—C12—C13	−0.3 (3)
C2—C1—C6—C7	176.77 (18)	C11—C12—C13—C14	−1.1 (3)
N2—N1—C7—N3	−0.5 (2)	C12—C13—C14—C15	1.5 (3)
N2—N1—C7—C6	176.48 (17)	C13—C14—C15—C10	−0.5 (3)
C8—N3—C7—N1	1.8 (2)	C11—C10—C15—C14	−0.9 (3)
N4—N3—C7—N1	177.66 (16)	C9—C10—C15—C14	−178.48 (17)
C8—N3—C7—C6	−175.02 (18)	N2—C9—C16—C17	53.6 (2)
N4—N3—C7—C6	0.9 (3)	C10—C9—C16—C17	176.93 (16)
C5—C6—C7—N1	140.4 (2)	C9—C16—C17—O1	26.2 (3)
C1—C6—C7—N1	−36.5 (3)	C9—C16—C17—C18	−152.79 (18)
C5—C6—C7—N3	−43.1 (3)	O1—C17—C18—C19	162.63 (19)
C1—C6—C7—N3	139.9 (2)	C16—C17—C18—C19	−18.4 (3)
N1—N2—C8—N3	2.1 (2)	O1—C17—C18—C23	−17.1 (3)
C9—N2—C8—N3	175.54 (16)	C16—C17—C18—C23	161.87 (18)
N1—N2—C8—S1	−177.12 (14)	C23—C18—C19—C20	0.8 (3)
C9—N2—C8—S1	−3.6 (3)	C17—C18—C19—C20	−178.92 (18)
C7—N3—C8—N2	−2.2 (2)	C18—C19—C20—C21	−0.5 (3)
N4—N3—C8—N2	−178.20 (15)	C19—C20—C21—C22	−0.7 (3)
C7—N3—C8—S1	176.97 (14)	C20—C21—C22—C23	1.5 (3)
N4—N3—C8—S1	1.0 (3)	C21—C22—C23—C18	−1.2 (3)
C8—N2—C9—C10	91.8 (2)	C19—C18—C23—C22	0.0 (3)
N1—N2—C9—C10	−95.16 (19)	C17—C18—C23—C22	179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1i	0.91 (2)	2.39 (2)	2.873 (3)	114.(2)
N4—H4A···S1	0.91 (2)	2.69 (2)	3.194 (2)	116.(2)
N4—H4B···S1i	0.91 (2)	2.66 (2)	3.490 (2)	151 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1i	0.91 (2)	2.39 (2)	2.873 (3)	114 (2)
N4—H4B⋯S1i	0.91 (2)	2.66 (2)	3.490 (2)	151 (2)

Symmetry code: (i) .