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

Wang, W.; Liu, Q.; Gao, Y.; Wu, W.; Xu, C.

doi:10.1107/S1600536811032983

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2379

doi:10.1107/S1600536811032983

Open

access

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

Wei Wang,^a,^b Qing-lei Liu,^a Yan Gao,^b Wen-peng Wu ^b and Chao Xu ^b ^*

^aSchool of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai 200235, People's Republic of China, and ^bSchool 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 7 August 2011; accepted 15 August 2011; online 27 August 2011)

In the title molecule, C₂₅H₂₁ClN₄OS, the triazole ring forms dihedral angles of 47.9 (2), 84.5 (2) and 3.9 (2)° with the two phenyl rings and the chlorophenyl ring, respectively. The chlorophenyl ring, the triazole ring and the conjugative linker between the two aromatic rings are nearly coplanar with an r.m.s. deviation of 0.0483 (2) Å and a maximum deviation of 0.0911 (2) Å.

Related literature

For the 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

C₂₅H₂₁ClN₄OS
M_r = 460.97
Triclinic, $[P \overline 1]$
a = 8.3347 (9) Å
b = 10.6029 (12) Å
c = 13.4262 (16) Å
α = 87.907 (19)°
β = 81.026 (18)°
γ = 82.024 (17)°
V = 1160.5 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 113 K
0.18 × 0.16 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.951, T_max = 0.973
14988 measured reflections
5478 independent reflections
3741 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.127
S = 1.02
5478 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.35 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811032983/zk2023sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032983/zk2023Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032983/zk2023Isup3.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 compound (I) are found to have normal values comparable with those reported in the related 1,2,4-triazole- 5(4H)-thione derivatives (Al-Tamimi et al., 1987; 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 101.84 (17)° (N1—C1—N3), 130.42 (15)°(N3—C1—S1), 110.66 (18)°(N2—C2—N3) and 126.39 (19) °(N2—C2—C25), which are similar to the reported triazole derivatives (Zhao et al., 2010; Gao et al., 2011). The 1,2,4-triazole ring forms the dihedral angles of 47.9 (2), 84.5 (2) and 3.9 (2)° with two phenyl rings and chlorophenyl rings, respectively. Three parts of chlorophenyl ring, triazole ring and the conjugative linker between this two armotic rings are nearly coplanar with an r.m.s. derivation of 0.0483 (2)Å and maximum deviation of 0.0911 (2) Å. The values of torsion angles N3—N4—C18—C19 [179.87 (17)°], N4—C18—C19—C20 [173.6 (2)°] and C2—N3—N4—C18 [173.88 (19)°] also confirm this results.

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 with the reaction of 2-chlorobenzaldehyde(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 colorless solid in 78% 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 60% probability level.

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

Crystal data top

C₂₅H₂₁ClN₄OS	Z = 2
M_r = 460.97	F(000) = 480
Triclinic, P1	D_x = 1.319 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3347 (9) Å	Cell parameters from 3699 reflections
b = 10.6029 (12) Å	θ = 1.5–27.9°
c = 13.4262 (16) Å	µ = 0.28 mm⁻¹
α = 87.907 (19)°	T = 113 K
β = 81.026 (18)°	Prism, colorless
γ = 82.024 (17)°	0.18 × 0.16 × 0.10 mm
V = 1160.5 (2) Å³

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5478 independent reflections
Radiation source: rotating anode	3741 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.047
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.8°, θ_min = 1.5°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −13→12
T_min = 0.951, T_max = 0.973	l = −17→17
14988 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0498P)²] where P = (F_o² + 2F_c²)/3
5478 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₅H₂₁ClN₄OS	γ = 82.024 (17)°
M_r = 460.97	V = 1160.5 (2) Å³
Triclinic, P1	Z = 2
a = 8.3347 (9) Å	Mo Kα radiation
b = 10.6029 (12) Å	µ = 0.28 mm⁻¹
c = 13.4262 (16) Å	T = 113 K
α = 87.907 (19)°	0.18 × 0.16 × 0.10 mm
β = 81.026 (18)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5478 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3741 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.973	R_int = 0.047
14988 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.02	Δρ_max = 0.23 e Å⁻³
5478 reflections	Δρ_min = −0.35 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
S1	0.29774 (8)	0.61784 (5)	0.10454 (4)	0.04087 (18)
Cl1	0.20199 (11)	0.93846 (6)	−0.11093 (5)	0.0681 (3)
O1	0.3085 (2)	0.22648 (14)	0.34675 (11)	0.0456 (4)
N1	0.4144 (2)	0.59915 (15)	0.28411 (12)	0.0313 (4)
N2	0.4657 (2)	0.66988 (15)	0.35541 (12)	0.0340 (4)
N3	0.3976 (2)	0.79060 (15)	0.22639 (12)	0.0309 (4)
N4	0.3676 (2)	0.90997 (15)	0.18009 (13)	0.0340 (4)
C1	0.3707 (3)	0.66863 (19)	0.20309 (15)	0.0309 (5)
C2	0.4535 (3)	0.78623 (19)	0.31822 (15)	0.0318 (5)
C3	0.4152 (3)	0.46078 (18)	0.30128 (15)	0.0313 (5)
H3	0.3646	0.4275	0.2465	0.038*
C4	0.3078 (3)	0.43869 (18)	0.40126 (15)	0.0353 (5)
H4A	0.2043	0.4980	0.4053	0.042*
H4B	0.3646	0.4583	0.4571	0.042*
C5	0.2675 (3)	0.3027 (2)	0.41478 (16)	0.0352 (5)
C6	0.1735 (3)	0.26640 (19)	0.51340 (16)	0.0332 (5)
C7	0.1321 (3)	0.1420 (2)	0.52621 (17)	0.0414 (6)
H7	0.1621	0.0838	0.4722	0.050*
C8	0.0481 (3)	0.1038 (2)	0.61687 (19)	0.0459 (6)
H8	0.0223	0.0193	0.6254	0.055*
C9	0.0018 (3)	0.1891 (2)	0.69522 (18)	0.0445 (6)
H9	−0.0565	0.1629	0.7573	0.053*
C10	0.0399 (3)	0.3124 (2)	0.68346 (17)	0.0424 (6)
H10	0.0071	0.3707	0.7372	0.051*
C11	0.1257 (3)	0.3505 (2)	0.59356 (16)	0.0375 (5)
H11	0.1525	0.4349	0.5862	0.045*
C12	0.5930 (3)	0.39735 (18)	0.29147 (15)	0.0327 (5)
C13	0.6642 (3)	0.34362 (19)	0.37317 (17)	0.0400 (6)
H13	0.6004	0.3426	0.4383	0.048*
C14	0.8284 (3)	0.2916 (2)	0.3594 (2)	0.0516 (7)
H14	0.8759	0.2543	0.4153	0.062*
C15	0.9234 (3)	0.2933 (2)	0.2655 (2)	0.0551 (7)
H15	1.0360	0.2586	0.2571	0.066*
C16	0.8540 (3)	0.3458 (2)	0.1841 (2)	0.0543 (7)
H16	0.9188	0.3470	0.1193	0.065*
C17	0.6896 (3)	0.3970 (2)	0.19660 (17)	0.0429 (6)
H17	0.6423	0.4322	0.1400	0.051*
C18	0.3300 (3)	0.91863 (19)	0.09206 (15)	0.0341 (5)
H18	0.3212	0.8449	0.0562	0.041*
C19	0.3002 (3)	1.04705 (19)	0.04715 (15)	0.0318 (5)
C20	0.2424 (3)	1.0664 (2)	−0.04535 (16)	0.0405 (6)
C21	0.2152 (3)	1.1880 (2)	−0.08722 (18)	0.0469 (6)
H21	0.1754	1.1999	−0.1499	0.056*
C22	0.2463 (3)	1.2909 (2)	−0.03757 (18)	0.0473 (6)
H22	0.2267	1.3740	−0.0658	0.057*
C23	0.3057 (3)	1.2743 (2)	0.05313 (18)	0.0479 (6)
H23	0.3284	1.3458	0.0865	0.057*
C24	0.3322 (3)	1.1538 (2)	0.09534 (17)	0.0412 (6)
H24	0.3728	1.1432	0.1579	0.049*
C25	0.4944 (3)	0.9002 (2)	0.36488 (17)	0.0429 (6)
H25A	0.5084	0.8804	0.4351	0.064*
H25B	0.4054	0.9706	0.3628	0.064*
H25C	0.5964	0.9248	0.3275	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0663 (4)	0.0293 (3)	0.0291 (3)	−0.0053 (3)	−0.0155 (3)	0.0028 (2)
Cl1	0.1153 (7)	0.0498 (4)	0.0527 (4)	−0.0258 (4)	−0.0429 (4)	0.0075 (3)
O1	0.0627 (12)	0.0358 (9)	0.0392 (9)	−0.0074 (8)	−0.0097 (8)	−0.0028 (7)
N1	0.0427 (11)	0.0253 (9)	0.0255 (9)	0.0001 (8)	−0.0093 (8)	0.0029 (7)
N2	0.0422 (11)	0.0294 (10)	0.0318 (10)	−0.0014 (8)	−0.0130 (8)	0.0007 (8)
N3	0.0379 (11)	0.0245 (9)	0.0297 (9)	−0.0008 (7)	−0.0074 (8)	0.0052 (7)
N4	0.0413 (11)	0.0263 (10)	0.0343 (10)	−0.0025 (8)	−0.0097 (8)	0.0074 (8)
C1	0.0385 (13)	0.0263 (11)	0.0258 (10)	0.0000 (9)	−0.0030 (9)	0.0036 (9)
C2	0.0366 (13)	0.0297 (12)	0.0300 (11)	0.0001 (9)	−0.0118 (9)	0.0014 (9)
C3	0.0427 (13)	0.0225 (11)	0.0287 (11)	−0.0015 (9)	−0.0087 (10)	0.0035 (8)
C4	0.0417 (14)	0.0294 (12)	0.0329 (12)	0.0003 (9)	−0.0056 (10)	0.0040 (9)
C5	0.0415 (14)	0.0311 (12)	0.0346 (12)	−0.0022 (10)	−0.0140 (10)	0.0053 (10)
C6	0.0352 (12)	0.0317 (12)	0.0344 (12)	−0.0033 (9)	−0.0133 (10)	0.0069 (9)
C7	0.0438 (14)	0.0366 (13)	0.0469 (14)	−0.0085 (10)	−0.0153 (11)	0.0054 (11)
C8	0.0456 (15)	0.0404 (14)	0.0563 (16)	−0.0148 (11)	−0.0179 (12)	0.0178 (12)
C9	0.0339 (13)	0.0569 (16)	0.0442 (14)	−0.0119 (11)	−0.0106 (11)	0.0193 (12)
C10	0.0413 (14)	0.0456 (14)	0.0389 (13)	−0.0035 (11)	−0.0061 (11)	0.0070 (11)
C11	0.0390 (14)	0.0346 (13)	0.0395 (13)	−0.0049 (10)	−0.0096 (10)	0.0070 (10)
C12	0.0417 (13)	0.0235 (11)	0.0324 (11)	−0.0001 (9)	−0.0088 (10)	0.0003 (9)
C13	0.0473 (15)	0.0352 (13)	0.0373 (12)	0.0020 (10)	−0.0122 (11)	−0.0012 (10)
C14	0.0530 (17)	0.0395 (14)	0.0663 (18)	0.0049 (12)	−0.0305 (14)	−0.0033 (12)
C15	0.0390 (15)	0.0451 (15)	0.081 (2)	0.0027 (11)	−0.0110 (15)	−0.0169 (14)
C16	0.0486 (17)	0.0509 (16)	0.0592 (17)	−0.0033 (12)	0.0038 (14)	−0.0092 (13)
C17	0.0487 (16)	0.0398 (14)	0.0388 (13)	−0.0036 (11)	−0.0046 (12)	0.0002 (10)
C18	0.0429 (14)	0.0274 (12)	0.0313 (11)	−0.0033 (9)	−0.0056 (10)	0.0025 (9)
C19	0.0354 (12)	0.0270 (11)	0.0321 (11)	−0.0044 (9)	−0.0034 (9)	0.0033 (9)
C20	0.0521 (15)	0.0367 (13)	0.0352 (12)	−0.0093 (11)	−0.0127 (11)	0.0065 (10)
C21	0.0556 (16)	0.0444 (15)	0.0423 (14)	−0.0065 (12)	−0.0158 (12)	0.0130 (12)
C22	0.0564 (17)	0.0329 (14)	0.0504 (15)	−0.0003 (11)	−0.0097 (13)	0.0121 (11)
C23	0.0701 (19)	0.0294 (13)	0.0453 (14)	−0.0085 (11)	−0.0115 (13)	0.0023 (11)
C24	0.0535 (16)	0.0344 (13)	0.0352 (12)	−0.0054 (11)	−0.0066 (11)	0.0025 (10)
C25	0.0532 (16)	0.0343 (13)	0.0450 (13)	−0.0036 (11)	−0.0219 (12)	0.0005 (10)

Geometric parameters (Å, º) top

S1—C1	1.675 (2)	C10—H10	0.9500
Cl1—C20	1.742 (2)	C11—H11	0.9500
O1—C5	1.218 (2)	C12—C13	1.394 (3)
N1—C1	1.360 (2)	C12—C17	1.396 (3)
N1—N2	1.389 (2)	C13—C14	1.390 (3)
N1—C3	1.476 (2)	C13—H13	0.9500
N2—C2	1.311 (2)	C14—C15	1.381 (3)
N3—C2	1.381 (2)	C14—H14	0.9500
N3—C1	1.397 (2)	C15—C16	1.380 (3)
N3—N4	1.398 (2)	C15—H15	0.9500
N4—C18	1.266 (2)	C16—C17	1.389 (3)
C2—C25	1.485 (3)	C16—H16	0.9500
C3—C4	1.523 (3)	C17—H17	0.9500
C3—C12	1.528 (3)	C18—C19	1.474 (3)
C3—H3	1.0000	C18—H18	0.9500
C4—C5	1.524 (3)	C19—C20	1.399 (3)
C4—H4A	0.9900	C19—C24	1.401 (3)
C4—H4B	0.9900	C20—C21	1.392 (3)
C5—C6	1.496 (3)	C21—C22	1.373 (3)
C6—C11	1.396 (3)	C21—H21	0.9500
C6—C7	1.407 (3)	C22—C23	1.381 (3)
C7—C8	1.383 (3)	C22—H22	0.9500
C7—H7	0.9500	C23—C24	1.383 (3)
C8—C9	1.385 (3)	C23—H23	0.9500
C8—H8	0.9500	C24—H24	0.9500
C9—C10	1.385 (3)	C25—H25A	0.9800
C9—H9	0.9500	C25—H25B	0.9800
C10—C11	1.381 (3)	C25—H25C	0.9800

C1—N1—N2	114.03 (16)	C6—C11—H11	119.6
C1—N1—C3	127.05 (17)	C13—C12—C17	118.7 (2)
N2—N1—C3	118.91 (15)	C13—C12—C3	123.07 (19)
C2—N2—N1	104.23 (16)	C17—C12—C3	118.17 (18)
C2—N3—C1	109.24 (16)	C14—C13—C12	120.0 (2)
C2—N3—N4	117.55 (17)	C14—C13—H13	120.0
C1—N3—N4	133.00 (17)	C12—C13—H13	120.0
C18—N4—N3	120.21 (18)	C15—C14—C13	120.8 (2)
N1—C1—N3	101.84 (17)	C15—C14—H14	119.6
N1—C1—S1	127.71 (16)	C13—C14—H14	119.6
N3—C1—S1	130.42 (15)	C16—C15—C14	119.7 (2)
N2—C2—N3	110.66 (18)	C16—C15—H15	120.2
N2—C2—C25	126.39 (19)	C14—C15—H15	120.2
N3—C2—C25	122.95 (18)	C15—C16—C17	120.1 (2)
N1—C3—C4	108.79 (16)	C15—C16—H16	119.9
N1—C3—C12	108.60 (17)	C17—C16—H16	119.9
C4—C3—C12	115.85 (17)	C16—C17—C12	120.7 (2)
N1—C3—H3	107.8	C16—C17—H17	119.7
C4—C3—H3	107.8	C12—C17—H17	119.7
C12—C3—H3	107.8	N4—C18—C19	117.7 (2)
C3—C4—C5	112.93 (17)	N4—C18—H18	121.1
C3—C4—H4A	109.0	C19—C18—H18	121.1
C5—C4—H4A	109.0	C20—C19—C24	117.85 (19)
C3—C4—H4B	109.0	C20—C19—C18	121.47 (19)
C5—C4—H4B	109.0	C24—C19—C18	120.7 (2)
H4A—C4—H4B	107.8	C21—C20—C19	121.0 (2)
O1—C5—C6	121.09 (19)	C21—C20—Cl1	118.29 (18)
O1—C5—C4	120.94 (19)	C19—C20—Cl1	120.74 (16)
C6—C5—C4	117.96 (18)	C22—C21—C20	119.7 (2)
C11—C6—C7	118.5 (2)	C22—C21—H21	120.1
C11—C6—C5	122.84 (19)	C20—C21—H21	120.1
C7—C6—C5	118.63 (19)	C21—C22—C23	120.5 (2)
C8—C7—C6	120.5 (2)	C21—C22—H22	119.8
C8—C7—H7	119.8	C23—C22—H22	119.8
C6—C7—H7	119.8	C22—C23—C24	120.0 (2)
C7—C8—C9	119.9 (2)	C22—C23—H23	120.0
C7—C8—H8	120.0	C24—C23—H23	120.0
C9—C8—H8	120.0	C23—C24—C19	120.9 (2)
C10—C9—C8	120.3 (2)	C23—C24—H24	119.6
C10—C9—H9	119.8	C19—C24—H24	119.6
C8—C9—H9	119.8	C2—C25—H25A	109.5
C11—C10—C9	120.0 (2)	C2—C25—H25B	109.5
C11—C10—H10	120.0	H25A—C25—H25B	109.5
C9—C10—H10	120.0	C2—C25—H25C	109.5
C10—C11—C6	120.7 (2)	H25A—C25—H25C	109.5
C10—C11—H11	119.6	H25B—C25—H25C	109.5

C1—N1—N2—C2	0.1 (2)	C6—C7—C8—C9	1.1 (3)
C3—N1—N2—C2	178.94 (17)	C7—C8—C9—C10	−0.4 (3)
C2—N3—N4—C18	173.88 (19)	C8—C9—C10—C11	−0.5 (3)
C1—N3—N4—C18	−12.1 (3)	C9—C10—C11—C6	0.6 (3)
N2—N1—C1—N3	0.1 (2)	C7—C6—C11—C10	0.1 (3)
C3—N1—C1—N3	−178.57 (17)	C5—C6—C11—C10	−179.6 (2)
N2—N1—C1—S1	−177.92 (15)	N1—C3—C12—C13	110.5 (2)
C3—N1—C1—S1	3.4 (3)	C4—C3—C12—C13	−12.2 (3)
C2—N3—C1—N1	−0.3 (2)	N1—C3—C12—C17	−67.4 (2)
N4—N3—C1—N1	−174.73 (19)	C4—C3—C12—C17	169.86 (18)
C2—N3—C1—S1	177.65 (17)	C17—C12—C13—C14	0.3 (3)
N4—N3—C1—S1	3.3 (3)	C3—C12—C13—C14	−177.7 (2)
N1—N2—C2—N3	−0.3 (2)	C12—C13—C14—C15	0.7 (4)
N1—N2—C2—C25	−179.7 (2)	C13—C14—C15—C16	−0.9 (4)
C1—N3—C2—N2	0.4 (2)	C14—C15—C16—C17	0.2 (4)
N4—N3—C2—N2	175.82 (17)	C15—C16—C17—C12	0.7 (4)
C1—N3—C2—C25	179.84 (19)	C13—C12—C17—C16	−0.9 (3)
N4—N3—C2—C25	−4.8 (3)	C3—C12—C17—C16	177.1 (2)
C1—N1—C3—C4	−123.5 (2)	N3—N4—C18—C19	−179.87 (17)
N2—N1—C3—C4	57.9 (2)	N4—C18—C19—C20	−173.6 (2)
C1—N1—C3—C12	109.6 (2)	N4—C18—C19—C24	7.7 (3)
N2—N1—C3—C12	−69.1 (2)	C24—C19—C20—C21	−1.0 (3)
N1—C3—C4—C5	166.45 (17)	C18—C19—C20—C21	−179.8 (2)
C12—C3—C4—C5	−70.9 (2)	C24—C19—C20—Cl1	179.18 (17)
C3—C4—C5—O1	−5.8 (3)	C18—C19—C20—Cl1	0.4 (3)
C3—C4—C5—C6	175.37 (18)	C19—C20—C21—C22	0.4 (4)
O1—C5—C6—C11	179.3 (2)	Cl1—C20—C21—C22	−179.82 (19)
C4—C5—C6—C11	−1.8 (3)	C20—C21—C22—C23	0.6 (4)
O1—C5—C6—C7	−0.3 (3)	C21—C22—C23—C24	−0.9 (4)
C4—C5—C6—C7	178.57 (19)	C22—C23—C24—C19	0.2 (4)
C11—C6—C7—C8	−0.9 (3)	C20—C19—C24—C23	0.7 (3)
C5—C6—C7—C8	178.70 (19)	C18—C19—C24—C23	179.5 (2)

Experimental details

Crystal data
Chemical formula	C₂₅H₂₁ClN₄OS
M_r	460.97
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	8.3347 (9), 10.6029 (12), 13.4262 (16)
α, β, γ (°)	87.907 (19), 81.026 (18), 82.024 (17)
V (Å³)	1160.5 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.18 × 0.16 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.951, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	14988, 5478, 3741
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.127, 1.02
No. of reflections	5478
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.35

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

Acknowledgements

We gratefully acknowledge support by the Key Laboratory Project of Liaoning Province (No. 2008S127) and the Doctoral Starting Foundation of Liaoning Province (No. 20071103).

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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.