N-[(E)-2-Chloro­benzyl­idene]-3-(4-methyl­benzyl­sulfan­yl)-5-(3,4,5-trimethoxy­phen­yl)-4H-1,2,4-triazol-4-amine

Li, Q.-Z.; Song, B.-A.; Yang, S.; Zheng, Y.-G.; Guo, Q.-Q.

doi:10.1107/S1600536809009842

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o869

doi:10.1107/S1600536809009842

Open

access

N-[(E)-2-Chlorobenzylidene]-3-(4-methylbenzylsulfanyl)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-amine

Qian-Zhu Li,^a,^b ^* Bao-An Song,^a Song Yang,^a Yu-Guo Zheng ^a and Qing-Qing Guo ^a

^aCenter for Research and Development of Fine Chemicals, Guizhou University, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guiyang 550025, People's Republic of China, and ^bDepartment of Chemistry, Bijie University, Bijie 551700, People's Republic of China
^*Correspondence e-mail: qianzhuli77@yahoo.com.cn

(Received 22 February 2009; accepted 17 March 2009; online 25 March 2009)

In the title compound, C₂₆H₂₅ClN₄O₃S, the acyclic imine group exhibits an E configuration. The triazole ring is oriented at dihedral angles of 53.84 (2), 70.77 (1) and 32.59 (3)° with respect to the benzene rings of the 2-chlorobenzylidene, 4-methylbenzylsulfanyl and 3,4,5-trimethoxyphenyl groups, respectively. The crystal packing is stabilized by weak intermolecular C—H⋯N, C—H⋯S and C—H⋯π interactions.

Related literature

For more information on 1,2,4-triazoles, see: He et al. (2006 ); Kritsanida et al. (2002 ); Demirbas et al. (2002 ); Chattopadhyay & Ghosh (1987 , 1989 ).

Experimental

Crystal data

C₂₆H₂₅ClN₄O₃S
M_r = 509.01
Monoclinic, P 2₁ /c
a = 11.283 (4) Å
b = 7.414 (2) Å
c = 31.087 (10) Å
β = 100.961 (14)°
V = 2553.1 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.32 × 0.26 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.932, T_max = 0.956
26288 measured reflections
4590 independent reflections
3809 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.141
S = 1.03
4590 reflections
320 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯N4	0.93	2.52	3.000 (3)	112
C10—H10⋯S1	0.93	2.81	3.184 (3)	105
C6—H6⋯N1ⁱ	0.93	2.61	3.409 (3)	144
C8—H8B⋯Cg2ⁱⁱ	0.97	2.70	3.427 (2)	133
C24—H24B⋯Cg1ⁱⁱⁱ	0.96	2.94	3.588 (2)	125
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+2, -z; (iii) x, y-1, z. Cg1 is the centroid of the C9,C17,N1–N3 ring and Cg2 is the centroid of the C2–C7 ring.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009842/gk2192sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009842/gk2192Isup2.hkl

checkCIF report

Comment top

The design and synthesis of new 1,2,4-triazole derivatives is an important research field, since these species not only can be used to build polymetallic complexes (He et al., 2006), but also show biological activity (Demirbas et al., 2002; Kritsanida et al., 2002). The biological activity is most probably due to the presence of the –N–C–S unit (Chattopadhyay & Ghosh, 1987, 1989). We are interested in the synthesis and biological activities of 1,2,4-triazole derivatives and report herein the synthesis and crystal structure of the title compound.

As illustrated in Figure 1, the 2-chlorobenzylidene, 4-methylbenzylsulfanyl, 3,4,5-trimethoxyphenyl and 1,2,4-triazole fragments are not coplanar with each other. The triazole ring is oriented with respect to the phenyl rings of 2-chlorobenzylidene, 4-methylbenzylthio and 3,4,5-trimethoxyphenyl units at dihedral angles of 53.84 (2)°, 70.77 (1) ° and 32.59 (3) °, respectively. The molecular packing is consolidated through weak inter- and intramolecular C—H···N, C—H···S and C—H···π interactions. C—H···π interactions of methylene H atoms and methyl H atoms are established towards the π-systems of neighboring aromatic groups from 4-methylbenzylsulfanyl and 1,2,4-triazole units (Table 1, Fig. 2, Cg1 = ring(C9,C17,N1—N3); Cg2 = ring(C2—C7)). ;

Related literature top

For more information on 1,2,4-triazoles, see: He et al. (2006); Kritsanida et al. (2002); Demirbas et al. (2002); Chattopadhyay & Ghosh (1987, 1989). Cg1 is the centroid of the C9,C17,N1–N3 ring and Cg2 is the centroid of the C2—C7 ring.

Experimental top

A mixture of 1-chloromethyl-4-methylbenzene (1.40 g, 0.01 mol) and methanol (5 ml) was added dropwise to a stirred solution of (E)-4-(2-chlorobenzylideneamino)-5-(3,4,5-trimethoxyphenyl) -4H-1,2,4-triazole-3-thiol (4.05 g, 0.01 mol) and sodium hydroxide (0.40 g, 0.01 mol) in water (20 ml). The resulting mixture was stirred at room temperature for 5 h. The precipitate formed was filtered off and recrystallized from ethanol to give pure title compound, which was then dissolved in 30 ml ethanol, and single crystals of the title compound were obtained after several days.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound, showing the atomic numbering scheme. Non-hydrogen atoms are shown with 30% probability displacement ellipsoids.Hydrogen atoms have been omitted for clarity.
	Fig. 2. A packing view of the title compound. The interιntra molecluar C—H···N, C—H···S and C—H···π interactions are shown as dashed lines.
	Fig. 3. The synthesis procedure of the title compound.

N-[(E)-2-Chlorobenzylidene]-3-(4-methylbenzylsulfanyl)- 5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-amine top

Crystal data top

C₂₆H₂₅ClN₄O₃S	F(000) = 1064
M_r = 509.01	D_x = 1.324 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2895 reflections
a = 11.283 (4) Å	θ = 2.4–27.9°
b = 7.414 (2) Å	µ = 0.27 mm⁻¹
c = 31.087 (10) Å	T = 293 K
β = 100.961 (14)°	Block, colorless
V = 2553.1 (14) Å³	0.32 × 0.26 × 0.22 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4590 independent reflections
Radiation source: fine-focus sealed tube	3809 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 25.2°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.932, T_max = 0.956	k = −8→8
26288 measured reflections	l = −36→37

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0627P)² + 1.5591P] where P = (F_o² + 2F_c²)/3
4590 reflections	(Δ/σ)_max < 0.001
320 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

C₂₆H₂₅ClN₄O₃S	V = 2553.1 (14) Å³
M_r = 509.01	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.283 (4) Å	µ = 0.27 mm⁻¹
b = 7.414 (2) Å	T = 293 K
c = 31.087 (10) Å	0.32 × 0.26 × 0.22 mm
β = 100.961 (14)°

Data collection top

Bruker APEXII CCD diffractometer	4590 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3809 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.956	R_int = 0.028
26288 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.03	Δρ_max = 0.50 e Å⁻³
4590 reflections	Δρ_min = −0.65 e Å⁻³
320 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
Cl1	0.73726 (9)	0.3490 (3)	0.20121 (5)	0.1603 (7)
S1	0.49049 (6)	0.68103 (9)	0.095977 (19)	0.0586 (2)
O1	0.0266 (2)	−0.2541 (3)	0.08517 (7)	0.0766 (6)
O2	−0.03565 (19)	−0.1835 (3)	0.16218 (6)	0.0837 (7)
O3	0.01561 (19)	0.1311 (4)	0.20215 (6)	0.0879 (7)
N1	0.23855 (18)	0.3418 (3)	0.04765 (6)	0.0526 (5)
N2	0.32532 (18)	0.4699 (3)	0.04284 (6)	0.0540 (5)
N3	0.32908 (16)	0.4276 (2)	0.11267 (5)	0.0454 (4)
N4	0.35963 (19)	0.4375 (3)	0.15859 (6)	0.0556 (5)
C1	0.8350 (3)	1.3689 (5)	0.06633 (12)	0.0904 (10)
H1A	0.9129	1.3283	0.0623	0.136*
H1B	0.8412	1.4179	0.0953	0.136*
H1C	0.8059	1.4603	0.0451	0.136*
C2	0.7483 (2)	1.2123 (4)	0.06056 (8)	0.0575 (6)
C3	0.6369 (3)	1.2265 (4)	0.07290 (9)	0.0628 (7)
H3	0.6165	1.3333	0.0854	0.075*
C4	0.5560 (2)	1.0857 (4)	0.06705 (8)	0.0601 (6)
H4	0.4817	1.0987	0.0755	0.072*
C5	0.5842 (2)	0.9248 (3)	0.04874 (7)	0.0507 (5)
C6	0.6947 (2)	0.9099 (3)	0.03637 (8)	0.0576 (6)
H6	0.7157	0.8031	0.0240	0.069*
C7	0.7742 (2)	1.0521 (4)	0.04224 (8)	0.0622 (7)
H7	0.8481	1.0394	0.0335	0.075*
C8	0.4967 (3)	0.7699 (4)	0.04208 (8)	0.0670 (7)
H8A	0.5239	0.6775	0.0241	0.080*
H8B	0.4175	0.8109	0.0276	0.080*
C9	0.3782 (2)	0.5188 (3)	0.08193 (7)	0.0474 (5)
C10	0.4692 (2)	0.4112 (4)	0.17385 (8)	0.0602 (6)
H10	0.5216	0.3890	0.1547	0.072*
C11	0.5165 (3)	0.4147 (4)	0.22074 (8)	0.0654 (7)
C12	0.6388 (3)	0.3897 (5)	0.23688 (11)	0.0956 (12)
C13	0.6842 (4)	0.3889 (7)	0.28080 (14)	0.1259 (18)
H13	0.7664	0.3714	0.2910	0.151*
C14	0.6090 (5)	0.4138 (6)	0.30980 (13)	0.1222 (18)
H14	0.6403	0.4145	0.3397	0.147*
C15	0.4867 (4)	0.4380 (5)	0.29504 (10)	0.1005 (12)
H15	0.4353	0.4536	0.3148	0.121*
C16	0.4418 (3)	0.4389 (4)	0.25060 (9)	0.0777 (8)
H16	0.3596	0.4562	0.2406	0.093*
C17	0.24118 (19)	0.3193 (3)	0.08948 (7)	0.0441 (5)
C18	0.16596 (19)	0.1926 (3)	0.10855 (7)	0.0467 (5)
C19	0.1265 (2)	0.2324 (4)	0.14714 (7)	0.0555 (6)
H19	0.1468	0.3417	0.1613	0.067*
C20	0.0568 (2)	0.1077 (4)	0.16425 (7)	0.0610 (7)
C21	0.0254 (2)	−0.0554 (4)	0.14312 (8)	0.0602 (7)
C22	0.0629 (2)	−0.0922 (3)	0.10397 (8)	0.0549 (6)
C23	0.1337 (2)	0.0316 (3)	0.08673 (7)	0.0496 (5)
H23	0.1594	0.0065	0.0607	0.060*
C24	0.0497 (3)	−0.2881 (4)	0.04262 (11)	0.0803 (9)
H24A	0.0168	−0.4034	0.0326	0.120*
H24B	0.1353	−0.2882	0.0436	0.120*
H24C	0.0127	−0.1957	0.0229	0.120*
C25	−0.1619 (3)	−0.1711 (6)	0.15166 (12)	0.1129 (15)
H52A	−0.1969	−0.2613	0.1675	0.169*
H52B	−0.1884	−0.1897	0.1208	0.169*
H52C	−0.1868	−0.0537	0.1595	0.169*
C26	0.0534 (3)	0.2903 (6)	0.22675 (11)	0.1093 (15)
H51A	0.0185	0.2923	0.2526	0.164*
H51B	0.0274	0.3946	0.2092	0.164*
H51C	0.1399	0.2910	0.2350	0.164*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0661 (6)	0.2676 (19)	0.1397 (10)	−0.0097 (8)	0.0008 (6)	0.0368 (11)
S1	0.0758 (4)	0.0572 (4)	0.0401 (3)	−0.0246 (3)	0.0041 (3)	0.0012 (3)
O1	0.0976 (15)	0.0598 (11)	0.0769 (13)	−0.0293 (11)	0.0278 (11)	−0.0043 (10)
O2	0.0840 (14)	0.1055 (17)	0.0620 (12)	−0.0282 (12)	0.0149 (10)	0.0257 (11)
O3	0.0803 (13)	0.142 (2)	0.0465 (10)	−0.0296 (13)	0.0240 (9)	−0.0154 (12)
N1	0.0573 (11)	0.0580 (12)	0.0409 (10)	−0.0129 (9)	0.0057 (8)	−0.0049 (9)
N2	0.0634 (12)	0.0568 (12)	0.0407 (10)	−0.0147 (10)	0.0074 (9)	−0.0014 (9)
N3	0.0525 (10)	0.0485 (10)	0.0333 (9)	−0.0078 (9)	0.0034 (7)	−0.0011 (8)
N4	0.0626 (13)	0.0667 (13)	0.0347 (9)	−0.0152 (10)	0.0018 (9)	−0.0041 (9)
C1	0.084 (2)	0.084 (2)	0.095 (2)	−0.0351 (18)	−0.0041 (18)	0.0141 (18)
C2	0.0582 (14)	0.0602 (15)	0.0507 (13)	−0.0121 (12)	0.0017 (11)	0.0112 (11)
C3	0.0749 (17)	0.0486 (14)	0.0661 (16)	−0.0038 (13)	0.0164 (13)	−0.0054 (12)
C4	0.0566 (14)	0.0632 (16)	0.0640 (15)	−0.0022 (12)	0.0202 (12)	0.0022 (13)
C5	0.0633 (14)	0.0513 (13)	0.0354 (11)	−0.0098 (11)	0.0039 (10)	0.0055 (10)
C6	0.0771 (17)	0.0533 (14)	0.0443 (13)	0.0041 (13)	0.0158 (11)	0.0028 (11)
C7	0.0558 (14)	0.0719 (18)	0.0606 (15)	0.0029 (13)	0.0151 (12)	0.0162 (13)
C8	0.0883 (19)	0.0647 (16)	0.0440 (13)	−0.0246 (15)	0.0027 (12)	0.0076 (12)
C9	0.0564 (13)	0.0434 (12)	0.0413 (12)	−0.0061 (10)	0.0068 (10)	0.0009 (9)
C10	0.0646 (16)	0.0654 (16)	0.0478 (13)	−0.0070 (13)	0.0037 (12)	0.0094 (12)
C11	0.0772 (18)	0.0624 (16)	0.0489 (14)	−0.0212 (14)	−0.0072 (13)	0.0105 (12)
C12	0.083 (2)	0.114 (3)	0.077 (2)	−0.037 (2)	−0.0177 (17)	0.0282 (19)
C13	0.117 (3)	0.147 (4)	0.088 (3)	−0.060 (3)	−0.047 (3)	0.040 (3)
C14	0.175 (5)	0.108 (3)	0.059 (2)	−0.059 (3)	−0.042 (3)	0.017 (2)
C15	0.156 (4)	0.094 (3)	0.0457 (16)	−0.030 (2)	0.0033 (19)	0.0046 (16)
C16	0.106 (2)	0.0747 (19)	0.0475 (14)	−0.0166 (17)	0.0013 (15)	0.0015 (14)
C17	0.0449 (11)	0.0462 (12)	0.0396 (11)	−0.0032 (9)	0.0039 (9)	−0.0044 (9)
C18	0.0419 (11)	0.0558 (13)	0.0403 (11)	−0.0035 (10)	0.0024 (9)	0.0001 (10)
C19	0.0525 (13)	0.0696 (16)	0.0436 (12)	−0.0080 (12)	0.0066 (10)	−0.0088 (11)
C20	0.0521 (13)	0.094 (2)	0.0372 (12)	−0.0081 (13)	0.0082 (10)	0.0009 (13)
C21	0.0555 (14)	0.0777 (18)	0.0460 (13)	−0.0160 (13)	0.0058 (10)	0.0113 (12)
C22	0.0547 (13)	0.0578 (14)	0.0505 (13)	−0.0087 (11)	0.0058 (11)	0.0044 (11)
C23	0.0512 (12)	0.0531 (13)	0.0443 (12)	−0.0063 (11)	0.0086 (10)	−0.0011 (10)
C24	0.093 (2)	0.0593 (17)	0.097 (2)	−0.0211 (16)	0.0402 (18)	−0.0241 (16)
C25	0.081 (2)	0.165 (4)	0.089 (2)	−0.055 (2)	0.0068 (18)	0.040 (2)
C26	0.097 (2)	0.172 (4)	0.067 (2)	−0.037 (3)	0.0355 (18)	−0.048 (2)

Geometric parameters (Å, º) top

Cl1—C12	1.738 (4)	C8—H8B	0.9700
S1—C9	1.741 (2)	C10—C11	1.454 (3)
S1—C8	1.814 (2)	C10—H10	0.9300
O1—C22	1.363 (3)	C11—C16	1.378 (4)
O1—C24	1.419 (3)	C11—C12	1.389 (4)
O2—C21	1.372 (3)	C12—C13	1.364 (5)
O2—C25	1.403 (4)	C13—C14	1.363 (7)
O3—C20	1.357 (3)	C13—H13	0.9300
O3—C26	1.427 (4)	C14—C15	1.380 (6)
N1—C17	1.306 (3)	C14—H14	0.9300
N1—N2	1.392 (3)	C15—C16	1.378 (4)
N2—C9	1.299 (3)	C15—H15	0.9300
N3—C17	1.370 (3)	C16—H16	0.9300
N3—C9	1.371 (3)	C17—C18	1.465 (3)
N3—N4	1.405 (2)	C18—C23	1.387 (3)
N4—C10	1.252 (3)	C18—C19	1.388 (3)
C1—C2	1.507 (4)	C19—C20	1.384 (4)
C1—H1A	0.9600	C19—H19	0.9300
C1—H1B	0.9600	C20—C21	1.390 (4)
C1—H1C	0.9600	C21—C22	1.390 (4)
C2—C7	1.373 (4)	C22—C23	1.389 (3)
C2—C3	1.385 (4)	C23—H23	0.9300
C3—C4	1.376 (4)	C24—H24A	0.9600
C3—H3	0.9300	C24—H24B	0.9600
C4—C5	1.385 (4)	C24—H24C	0.9600
C4—H4	0.9300	C25—H52A	0.9600
C5—C6	1.378 (4)	C25—H52B	0.9600
C5—C8	1.502 (3)	C25—H52C	0.9600
C6—C7	1.373 (4)	C26—H51A	0.9600
C6—H6	0.9300	C26—H51B	0.9600
C7—H7	0.9300	C26—H51C	0.9600
C8—H8A	0.9700

C9—S1—C8	99.98 (11)	C14—C13—C12	120.0 (4)
C22—O1—C24	117.6 (2)	C14—C13—H13	120.0
C21—O2—C25	115.1 (2)	C12—C13—H13	120.0
C20—O3—C26	117.0 (2)	C13—C14—C15	120.4 (3)
C17—N1—N2	108.12 (17)	C13—C14—H14	119.8
C9—N2—N1	107.29 (18)	C15—C14—H14	119.8
C17—N3—C9	105.72 (17)	C16—C15—C14	119.2 (4)
C17—N3—N4	125.33 (18)	C16—C15—H15	120.4
C9—N3—N4	128.95 (18)	C14—C15—H15	120.4
C10—N4—N3	114.2 (2)	C15—C16—C11	121.3 (4)
C2—C1—H1A	109.5	C15—C16—H16	119.4
C2—C1—H1B	109.5	C11—C16—H16	119.4
H1A—C1—H1B	109.5	N1—C17—N3	109.03 (19)
C2—C1—H1C	109.5	N1—C17—C18	125.44 (19)
H1A—C1—H1C	109.5	N3—C17—C18	125.48 (19)
H1B—C1—H1C	109.5	C23—C18—C19	120.5 (2)
C7—C2—C3	117.2 (2)	C23—C18—C17	118.2 (2)
C7—C2—C1	122.1 (3)	C19—C18—C17	121.3 (2)
C3—C2—C1	120.7 (3)	C20—C19—C18	119.3 (2)
C4—C3—C2	121.3 (2)	C20—C19—H19	120.4
C4—C3—H3	119.3	C18—C19—H19	120.4
C2—C3—H3	119.3	O3—C20—C19	124.2 (3)
C3—C4—C5	120.6 (2)	O3—C20—C21	115.0 (2)
C3—C4—H4	119.7	C19—C20—C21	120.8 (2)
C5—C4—H4	119.7	O2—C21—C20	120.1 (2)
C6—C5—C4	118.3 (2)	O2—C21—C22	120.3 (3)
C6—C5—C8	120.4 (2)	C20—C21—C22	119.4 (2)
C4—C5—C8	121.3 (2)	O1—C22—C23	124.3 (2)
C7—C6—C5	120.3 (2)	O1—C22—C21	115.5 (2)
C7—C6—H6	119.9	C23—C22—C21	120.1 (2)
C5—C6—H6	119.9	C18—C23—C22	119.8 (2)
C2—C7—C6	122.3 (2)	C18—C23—H23	120.1
C2—C7—H7	118.9	C22—C23—H23	120.1
C6—C7—H7	118.9	O1—C24—H24A	109.5
C5—C8—S1	106.86 (16)	O1—C24—H24B	109.5
C5—C8—H8A	110.3	H24A—C24—H24B	109.5
S1—C8—H8A	110.3	O1—C24—H24C	109.5
C5—C8—H8B	110.3	H24A—C24—H24C	109.5
S1—C8—H8B	110.3	H24B—C24—H24C	109.5
H8A—C8—H8B	108.6	O2—C25—H52A	109.5
N2—C9—N3	109.84 (19)	O2—C25—H52B	109.5
N2—C9—S1	127.60 (17)	H52A—C25—H52B	109.5
N3—C9—S1	122.51 (16)	O2—C25—H52C	109.5
N4—C10—C11	121.6 (3)	H52A—C25—H52C	109.5
N4—C10—H10	119.2	H52B—C25—H52C	109.5
C11—C10—H10	119.2	O3—C26—H51A	109.5
C16—C11—C12	117.8 (3)	O3—C26—H51B	109.5
C16—C11—C10	121.5 (3)	H51A—C26—H51B	109.5
C12—C11—C10	120.6 (3)	O3—C26—H51C	109.5
C13—C12—C11	121.3 (4)	H51A—C26—H51C	109.5
C13—C12—Cl1	118.3 (3)	H51B—C26—H51C	109.5
C11—C12—Cl1	120.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···N4	0.93	2.52	3.000 (3)	112
C10—H10···S1	0.93	2.81	3.184 (3)	105
C6—H6···N1ⁱ	0.93	2.61	3.409 (3)	144
C8—H8B···Cg2ⁱⁱ	0.97	2.70	3.427 (2)	133
C24—H24B···Cg1ⁱⁱⁱ	0.96	2.94	3.588 (2)	125

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+2, −z; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₅ClN₄O₃S
M_r	509.01
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.283 (4), 7.414 (2), 31.087 (10)
β (°)	100.961 (14)
V (Å³)	2553.1 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.32 × 0.26 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.932, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	26288, 4590, 3809
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.141, 1.03
No. of reflections	4590
No. of parameters	320
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.65

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···N4	0.93	2.52	3.000 (3)	112
C10—H10···S1	0.93	2.81	3.184 (3)	105
C6—H6···N1ⁱ	0.93	2.61	3.409 (3)	144.1
C8—H8B···Cg2ⁱⁱ	0.97	2.70	3.427 (2)	133
C24—H24B···Cg1ⁱⁱⁱ	0.96	2.94	3.588 (2)	125

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+2, −z; (iii) x, y−1, z.

Acknowledgements

The authors acknowledge the National Key Technologies R&D Program of China (2006BAE01A01–13) for supporting this work.

References

Brandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chattopadhyay, S. K. & Ghosh, S. (1987). Inorg. Chim. Acta, 131, 15-20. CrossRef CAS Web of Science Google Scholar
Chattopadhyay, S. K. & Ghosh, S. (1989). Inorg. Chim. Acta, 163, 245-253. CrossRef CAS Web of Science Google Scholar
Demirbas, N., Ugurluoglu, R. & Demirbas, A. (2002). Bioorg. Med. Chem. 10, 3717–3723. Web of Science CrossRef PubMed CAS Google Scholar
He, X., Lu, C. Z., Wu, C. D. & Chen, L. J. (2006). Eur. J. Inorg. Chem., pp. 2491–2503. Google Scholar
Kritsanida, M., Mouroutsou, A., Marakos, P., Pouli, N., Papakonstantinou- Garoufalias, S., Pannecouque, C., Witvrouw, M. & Clercq, E. D. (2002). Farmaco, 57, 253–257. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o869

doi:10.1107/S1600536809009842

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

N-[(E)-2-Chloro­benzyl­­idene]-3-(4-methyl­benzyl­sulfan­yl)-5-(3,4,5-tri­meth­oxy­phen­yl)-4H-1,2,4-triazol-4-amine

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-[(E)-2-Chlorobenzylidene]-3-(4-methylbenzylsulfanyl)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-amine