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

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ISSN: 2056-9890

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

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[He, X., Lu, C. Z., Wu, C. D. & Chen, L. J. (2006). Eur. J. Inorg. Chem., pp. 2491-2503.]); Kritsanida et al. (2002[Kritsanida, M., Mouroutsou, A., Marakos, P., Pouli, N., Papakonstantinou- Garoufalias, S., Pannecouque, C., Witvrouw, M. & Clercq, E. D. (2002). Farmaco, 57, 253-257.]); Demirbas et al. (2002[Demirbas, N., Ugurluoglu, R. & Demirbas, A. (2002). Bioorg. Med. Chem. 10, 3717-3723.]); Chattopadhyay & Ghosh (1987[Chattopadhyay, S. K. & Ghosh, S. (1987). Inorg. Chim. Acta, 131, 15-20.], 1989[Chattopadhyay, S. K. & Ghosh, S. (1989). Inorg. Chim. Acta, 163, 245-253.]).

[Scheme 1]

Experimental

Crystal data
  • C26H25ClN4O3S

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.932, Tmax = 0.956

  • 26288 measured reflections

  • 4590 independent reflections

  • 3809 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.141

  • S = 1.03

  • 4590 reflections

  • 320 parameters

  • H-atom parameters constrained

  • Δρmax = 0.50 e Å−3

  • Δρmin = −0.65 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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—H8BCg2ii 0.97 2.70 3.427 (2) 133
C24—H24BCg1iii 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[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2001[Brandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


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.

Refinement top

H atoms were placed in calculated positions and were treated as riding on the parent C atoms with C—H = 0.93 - 0.97 Å, and with Uiso(H) = xUeq(C), where x = 1.2 for CH2 and CH groups and x = 1.5 for CH3 group.

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
[Figure 1] 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.
[Figure 2] 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.
[Figure 3] 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
C26H25ClN4O3SF(000) = 1064
Mr = 509.01Dx = 1.324 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2895 reflections
a = 11.283 (4) Åθ = 2.4–27.9°
b = 7.414 (2) ŵ = 0.27 mm1
c = 31.087 (10) ÅT = 293 K
β = 100.961 (14)°Block, colorless
V = 2553.1 (14) Å30.32 × 0.26 × 0.22 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
4590 independent reflections
Radiation source: fine-focus sealed tube3809 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ϕ and ω scansθmax = 25.2°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.932, Tmax = 0.956k = 88
26288 measured reflectionsl = 3637
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0627P)2 + 1.5591P]
where P = (Fo2 + 2Fc2)/3
4590 reflections(Δ/σ)max < 0.001
320 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.65 e Å3
Crystal data top
C26H25ClN4O3SV = 2553.1 (14) Å3
Mr = 509.01Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.283 (4) ŵ = 0.27 mm1
b = 7.414 (2) ÅT = 293 K
c = 31.087 (10) Å0.32 × 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)
Tmin = 0.932, Tmax = 0.956Rint = 0.028
26288 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.141H-atom parameters constrained
S = 1.03Δρmax = 0.50 e Å3
4590 reflectionsΔρmin = 0.65 e Å3
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
xyzUiso*/Ueq
Cl10.73726 (9)0.3490 (3)0.20121 (5)0.1603 (7)
S10.49049 (6)0.68103 (9)0.095977 (19)0.0586 (2)
O10.0266 (2)0.2541 (3)0.08517 (7)0.0766 (6)
O20.03565 (19)0.1835 (3)0.16218 (6)0.0837 (7)
O30.01561 (19)0.1311 (4)0.20215 (6)0.0879 (7)
N10.23855 (18)0.3418 (3)0.04765 (6)0.0526 (5)
N20.32532 (18)0.4699 (3)0.04284 (6)0.0540 (5)
N30.32908 (16)0.4276 (2)0.11267 (5)0.0454 (4)
N40.35963 (19)0.4375 (3)0.15859 (6)0.0556 (5)
C10.8350 (3)1.3689 (5)0.06633 (12)0.0904 (10)
H1A0.91291.32830.06230.136*
H1B0.84121.41790.09530.136*
H1C0.80591.46030.04510.136*
C20.7483 (2)1.2123 (4)0.06056 (8)0.0575 (6)
C30.6369 (3)1.2265 (4)0.07290 (9)0.0628 (7)
H30.61651.33330.08540.075*
C40.5560 (2)1.0857 (4)0.06705 (8)0.0601 (6)
H40.48171.09870.07550.072*
C50.5842 (2)0.9248 (3)0.04874 (7)0.0507 (5)
C60.6947 (2)0.9099 (3)0.03637 (8)0.0576 (6)
H60.71570.80310.02400.069*
C70.7742 (2)1.0521 (4)0.04224 (8)0.0622 (7)
H70.84811.03940.03350.075*
C80.4967 (3)0.7699 (4)0.04208 (8)0.0670 (7)
H8A0.52390.67750.02410.080*
H8B0.41750.81090.02760.080*
C90.3782 (2)0.5188 (3)0.08193 (7)0.0474 (5)
C100.4692 (2)0.4112 (4)0.17385 (8)0.0602 (6)
H100.52160.38900.15470.072*
C110.5165 (3)0.4147 (4)0.22074 (8)0.0654 (7)
C120.6388 (3)0.3897 (5)0.23688 (11)0.0956 (12)
C130.6842 (4)0.3889 (7)0.28080 (14)0.1259 (18)
H130.76640.37140.29100.151*
C140.6090 (5)0.4138 (6)0.30980 (13)0.1222 (18)
H140.64030.41450.33970.147*
C150.4867 (4)0.4380 (5)0.29504 (10)0.1005 (12)
H150.43530.45360.31480.121*
C160.4418 (3)0.4389 (4)0.25060 (9)0.0777 (8)
H160.35960.45620.24060.093*
C170.24118 (19)0.3193 (3)0.08948 (7)0.0441 (5)
C180.16596 (19)0.1926 (3)0.10855 (7)0.0467 (5)
C190.1265 (2)0.2324 (4)0.14714 (7)0.0555 (6)
H190.14680.34170.16130.067*
C200.0568 (2)0.1077 (4)0.16425 (7)0.0610 (7)
C210.0254 (2)0.0554 (4)0.14312 (8)0.0602 (7)
C220.0629 (2)0.0922 (3)0.10397 (8)0.0549 (6)
C230.1337 (2)0.0316 (3)0.08673 (7)0.0496 (5)
H230.15940.00650.06070.060*
C240.0497 (3)0.2881 (4)0.04262 (11)0.0803 (9)
H24A0.01680.40340.03260.120*
H24B0.13530.28820.04360.120*
H24C0.01270.19570.02290.120*
C250.1619 (3)0.1711 (6)0.15166 (12)0.1129 (15)
H52A0.19690.26130.16750.169*
H52B0.18840.18970.12080.169*
H52C0.18680.05370.15950.169*
C260.0534 (3)0.2903 (6)0.22675 (11)0.1093 (15)
H51A0.01850.29230.25260.164*
H51B0.02740.39460.20920.164*
H51C0.13990.29100.23500.164*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0661 (6)0.2676 (19)0.1397 (10)0.0097 (8)0.0008 (6)0.0368 (11)
S10.0758 (4)0.0572 (4)0.0401 (3)0.0246 (3)0.0041 (3)0.0012 (3)
O10.0976 (15)0.0598 (11)0.0769 (13)0.0293 (11)0.0278 (11)0.0043 (10)
O20.0840 (14)0.1055 (17)0.0620 (12)0.0282 (12)0.0149 (10)0.0257 (11)
O30.0803 (13)0.142 (2)0.0465 (10)0.0296 (13)0.0240 (9)0.0154 (12)
N10.0573 (11)0.0580 (12)0.0409 (10)0.0129 (9)0.0057 (8)0.0049 (9)
N20.0634 (12)0.0568 (12)0.0407 (10)0.0147 (10)0.0074 (9)0.0014 (9)
N30.0525 (10)0.0485 (10)0.0333 (9)0.0078 (9)0.0034 (7)0.0011 (8)
N40.0626 (13)0.0667 (13)0.0347 (9)0.0152 (10)0.0018 (9)0.0041 (9)
C10.084 (2)0.084 (2)0.095 (2)0.0351 (18)0.0041 (18)0.0141 (18)
C20.0582 (14)0.0602 (15)0.0507 (13)0.0121 (12)0.0017 (11)0.0112 (11)
C30.0749 (17)0.0486 (14)0.0661 (16)0.0038 (13)0.0164 (13)0.0054 (12)
C40.0566 (14)0.0632 (16)0.0640 (15)0.0022 (12)0.0202 (12)0.0022 (13)
C50.0633 (14)0.0513 (13)0.0354 (11)0.0098 (11)0.0039 (10)0.0055 (10)
C60.0771 (17)0.0533 (14)0.0443 (13)0.0041 (13)0.0158 (11)0.0028 (11)
C70.0558 (14)0.0719 (18)0.0606 (15)0.0029 (13)0.0151 (12)0.0162 (13)
C80.0883 (19)0.0647 (16)0.0440 (13)0.0246 (15)0.0027 (12)0.0076 (12)
C90.0564 (13)0.0434 (12)0.0413 (12)0.0061 (10)0.0068 (10)0.0009 (9)
C100.0646 (16)0.0654 (16)0.0478 (13)0.0070 (13)0.0037 (12)0.0094 (12)
C110.0772 (18)0.0624 (16)0.0489 (14)0.0212 (14)0.0072 (13)0.0105 (12)
C120.083 (2)0.114 (3)0.077 (2)0.037 (2)0.0177 (17)0.0282 (19)
C130.117 (3)0.147 (4)0.088 (3)0.060 (3)0.047 (3)0.040 (3)
C140.175 (5)0.108 (3)0.059 (2)0.059 (3)0.042 (3)0.017 (2)
C150.156 (4)0.094 (3)0.0457 (16)0.030 (2)0.0033 (19)0.0046 (16)
C160.106 (2)0.0747 (19)0.0475 (14)0.0166 (17)0.0013 (15)0.0015 (14)
C170.0449 (11)0.0462 (12)0.0396 (11)0.0032 (9)0.0039 (9)0.0044 (9)
C180.0419 (11)0.0558 (13)0.0403 (11)0.0035 (10)0.0024 (9)0.0001 (10)
C190.0525 (13)0.0696 (16)0.0436 (12)0.0080 (12)0.0066 (10)0.0088 (11)
C200.0521 (13)0.094 (2)0.0372 (12)0.0081 (13)0.0082 (10)0.0009 (13)
C210.0555 (14)0.0777 (18)0.0460 (13)0.0160 (13)0.0058 (10)0.0113 (12)
C220.0547 (13)0.0578 (14)0.0505 (13)0.0087 (11)0.0058 (11)0.0044 (11)
C230.0512 (12)0.0531 (13)0.0443 (12)0.0063 (11)0.0086 (10)0.0011 (10)
C240.093 (2)0.0593 (17)0.097 (2)0.0211 (16)0.0402 (18)0.0241 (16)
C250.081 (2)0.165 (4)0.089 (2)0.055 (2)0.0068 (18)0.040 (2)
C260.097 (2)0.172 (4)0.067 (2)0.037 (3)0.0355 (18)0.048 (2)
Geometric parameters (Å, º) top
Cl1—C121.738 (4)C8—H8B0.9700
S1—C91.741 (2)C10—C111.454 (3)
S1—C81.814 (2)C10—H100.9300
O1—C221.363 (3)C11—C161.378 (4)
O1—C241.419 (3)C11—C121.389 (4)
O2—C211.372 (3)C12—C131.364 (5)
O2—C251.403 (4)C13—C141.363 (7)
O3—C201.357 (3)C13—H130.9300
O3—C261.427 (4)C14—C151.380 (6)
N1—C171.306 (3)C14—H140.9300
N1—N21.392 (3)C15—C161.378 (4)
N2—C91.299 (3)C15—H150.9300
N3—C171.370 (3)C16—H160.9300
N3—C91.371 (3)C17—C181.465 (3)
N3—N41.405 (2)C18—C231.387 (3)
N4—C101.252 (3)C18—C191.388 (3)
C1—C21.507 (4)C19—C201.384 (4)
C1—H1A0.9600C19—H190.9300
C1—H1B0.9600C20—C211.390 (4)
C1—H1C0.9600C21—C221.390 (4)
C2—C71.373 (4)C22—C231.389 (3)
C2—C31.385 (4)C23—H230.9300
C3—C41.376 (4)C24—H24A0.9600
C3—H30.9300C24—H24B0.9600
C4—C51.385 (4)C24—H24C0.9600
C4—H40.9300C25—H52A0.9600
C5—C61.378 (4)C25—H52B0.9600
C5—C81.502 (3)C25—H52C0.9600
C6—C71.373 (4)C26—H51A0.9600
C6—H60.9300C26—H51B0.9600
C7—H70.9300C26—H51C0.9600
C8—H8A0.9700
C9—S1—C899.98 (11)C14—C13—C12120.0 (4)
C22—O1—C24117.6 (2)C14—C13—H13120.0
C21—O2—C25115.1 (2)C12—C13—H13120.0
C20—O3—C26117.0 (2)C13—C14—C15120.4 (3)
C17—N1—N2108.12 (17)C13—C14—H14119.8
C9—N2—N1107.29 (18)C15—C14—H14119.8
C17—N3—C9105.72 (17)C16—C15—C14119.2 (4)
C17—N3—N4125.33 (18)C16—C15—H15120.4
C9—N3—N4128.95 (18)C14—C15—H15120.4
C10—N4—N3114.2 (2)C15—C16—C11121.3 (4)
C2—C1—H1A109.5C15—C16—H16119.4
C2—C1—H1B109.5C11—C16—H16119.4
H1A—C1—H1B109.5N1—C17—N3109.03 (19)
C2—C1—H1C109.5N1—C17—C18125.44 (19)
H1A—C1—H1C109.5N3—C17—C18125.48 (19)
H1B—C1—H1C109.5C23—C18—C19120.5 (2)
C7—C2—C3117.2 (2)C23—C18—C17118.2 (2)
C7—C2—C1122.1 (3)C19—C18—C17121.3 (2)
C3—C2—C1120.7 (3)C20—C19—C18119.3 (2)
C4—C3—C2121.3 (2)C20—C19—H19120.4
C4—C3—H3119.3C18—C19—H19120.4
C2—C3—H3119.3O3—C20—C19124.2 (3)
C3—C4—C5120.6 (2)O3—C20—C21115.0 (2)
C3—C4—H4119.7C19—C20—C21120.8 (2)
C5—C4—H4119.7O2—C21—C20120.1 (2)
C6—C5—C4118.3 (2)O2—C21—C22120.3 (3)
C6—C5—C8120.4 (2)C20—C21—C22119.4 (2)
C4—C5—C8121.3 (2)O1—C22—C23124.3 (2)
C7—C6—C5120.3 (2)O1—C22—C21115.5 (2)
C7—C6—H6119.9C23—C22—C21120.1 (2)
C5—C6—H6119.9C18—C23—C22119.8 (2)
C2—C7—C6122.3 (2)C18—C23—H23120.1
C2—C7—H7118.9C22—C23—H23120.1
C6—C7—H7118.9O1—C24—H24A109.5
C5—C8—S1106.86 (16)O1—C24—H24B109.5
C5—C8—H8A110.3H24A—C24—H24B109.5
S1—C8—H8A110.3O1—C24—H24C109.5
C5—C8—H8B110.3H24A—C24—H24C109.5
S1—C8—H8B110.3H24B—C24—H24C109.5
H8A—C8—H8B108.6O2—C25—H52A109.5
N2—C9—N3109.84 (19)O2—C25—H52B109.5
N2—C9—S1127.60 (17)H52A—C25—H52B109.5
N3—C9—S1122.51 (16)O2—C25—H52C109.5
N4—C10—C11121.6 (3)H52A—C25—H52C109.5
N4—C10—H10119.2H52B—C25—H52C109.5
C11—C10—H10119.2O3—C26—H51A109.5
C16—C11—C12117.8 (3)O3—C26—H51B109.5
C16—C11—C10121.5 (3)H51A—C26—H51B109.5
C12—C11—C10120.6 (3)O3—C26—H51C109.5
C13—C12—C11121.3 (4)H51A—C26—H51C109.5
C13—C12—Cl1118.3 (3)H51B—C26—H51C109.5
C11—C12—Cl1120.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···N40.932.523.000 (3)112
C10—H10···S10.932.813.184 (3)105
C6—H6···N1i0.932.613.409 (3)144
C8—H8B···Cg2ii0.972.703.427 (2)133
C24—H24B···Cg1iii0.962.943.588 (2)125
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+2, z; (iii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC26H25ClN4O3S
Mr509.01
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)11.283 (4), 7.414 (2), 31.087 (10)
β (°) 100.961 (14)
V3)2553.1 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.32 × 0.26 × 0.22
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.932, 0.956
No. of measured, independent and
observed [I > 2σ(I)] reflections
26288, 4590, 3809
Rint0.028
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.141, 1.03
No. of reflections4590
No. of parameters320
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C19—H19···N40.932.523.000 (3)112
C10—H10···S10.932.813.184 (3)105
C6—H6···N1i0.932.613.409 (3)144.1
C8—H8B···Cg2ii0.972.703.427 (2)133
C24—H24B···Cg1iii0.962.943.588 (2)125
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+2, z; (iii) x, y1, z.
 

Acknowledgements

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

References

First citationBrandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChattopadhyay, S. K. & Ghosh, S. (1987). Inorg. Chim. Acta, 131, 15-20.  CrossRef CAS Web of Science Google Scholar
First citationChattopadhyay, S. K. & Ghosh, S. (1989). Inorg. Chim. Acta, 163, 245-253.  CrossRef CAS Web of Science Google Scholar
First citationDemirbas, N., Ugurluoglu, R. & Demirbas, A. (2002). Bioorg. Med. Chem. 10, 3717–3723.  Web of Science CrossRef PubMed CAS Google Scholar
First citationHe, X., Lu, C. Z., Wu, C. D. & Chen, L. J. (2006). Eur. J. Inorg. Chem., pp. 2491–2503.  Google Scholar
First citationKritsanida, 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
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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