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ISSN: 2056-9890

rac-3-{4-[(Furan-2-ylmethyl­­idene)­amino]-3-methyl-5-sulfanyl­­idene-4,5-di­hydro-1H-1,2,4-triazol-1-yl}-1,3-di­phenyl­propan-1-one

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 6 August 2011; accepted 29 August 2011; online 30 September 2011)

In the title mol­ecule, C23H20N4O2S, the triazole ring forms dihedral angles of 150.3 (2), 77.3 (2) and 77.6 (2)°, respectively, with the furan ring and the phenyl rings. The furan ring is almost perpendicular to the central phenyl ring, making a dihedral angle of 86.0 (3)°.

Related literature

For the crystal structures of related 1,2,4-triazole-5(4H)-thione derivatives, see: Al-Tamimi et al. (2010[Al-Tamimi, A.-M. S., Bari, A., Al-Omar, M. A., Alrashood, K. A. & El-Emam, A. A. (2010). Acta Cryst. E66, o1756.]); Fun et al. (2009[Fun, H.-K., Chantrapromma, S., Sujith, K. V. & Kalluraya, B. (2009). Acta Cryst. E65, o495-o496.]); Gao et al. (2011[Gao, Y., Zhang, L. & Wang, H. (2011). Acta Cryst. E67, o1794.]); Tan et al. (2010[Tan, K. W., Maah, M. J. & Ng, S. W. (2010). Acta Cryst. E66, o2224.]); Wang et al. (2011[Wang, W., Gao, Y., Xiao, Z., Yao, H. & Zhang, J. (2011). Acta Cryst. E67, o269.]); Zhao et al. (2010[Zhao, B., Liu, Z., Gao, Y., Song, B. & Deng, Q. (2010). Acta Cryst. E66, o2814.]).

[Scheme 1]

Experimental

Crystal data
  • C23H20N4O2S

  • Mr = 416.50

  • Monoclinic, P 21 /c

  • a = 8.154 (3) Å

  • b = 21.194 (6) Å

  • c = 12.878 (4) Å

  • β = 107.965 (5)°

  • V = 2117.0 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.18 mm−1

  • T = 113 K

  • 0.24 × 0.20 × 0.12 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.958, Tmax = 0.979

  • 26979 measured reflections

  • 5030 independent reflections

  • 4229 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.106

  • S = 1.07

  • 5030 reflections

  • 272 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

In a continuation of structural studies by our group (Wang et al., 2011) of Mannich base derivatives synthesized by reactions of amino heterocycles and aromatic aldehydes, we present here the crystal structure of the title compound, C23H20N4O2S.

The bond lengths and angles in this compound are found to have values comparable with those reported in 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 Csp2 hybridization states with bond angles of 102.03 (10)° (N1—C1—N3), 131.01 (9)° (N3—C1—S1), 110.81 (11)° (N2—C2—N3) and 125.29 (12) ° (N2—C2—C23), which are similar to those in other reported triazole derivatives (Zhao et al., 2010; Gao et al., 2011). The 1,2,4-triazole ring forms dihedral angles of 150.3 (2), 77.3 (2) and 77.6 (2)° with the furan ring and the phenyl rings, respectively. The furan ring is almost perpendicular to the C12—C17 phenyl ring, with a dihedral angle of 94.0 (3)°.

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 in the reaction of 2-furfural (2.0 mmol) with 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 ethanol. 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 a colorless solid in 75% yield. Crystals suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform–ethanol (1:1).

Refinement top

Hydrogen atoms were positioned geometrically and refined as riding (C—H = 0.95–1.00 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Structure description top

In a continuation of structural studies by our group (Wang et al., 2011) of Mannich base derivatives synthesized by reactions of amino heterocycles and aromatic aldehydes, we present here the crystal structure of the title compound, C23H20N4O2S.

The bond lengths and angles in this compound are found to have values comparable with those reported in 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 Csp2 hybridization states with bond angles of 102.03 (10)° (N1—C1—N3), 131.01 (9)° (N3—C1—S1), 110.81 (11)° (N2—C2—N3) and 125.29 (12) ° (N2—C2—C23), which are similar to those in other reported triazole derivatives (Zhao et al., 2010; Gao et al., 2011). The 1,2,4-triazole ring forms dihedral angles of 150.3 (2), 77.3 (2) and 77.6 (2)° with the furan ring and the phenyl rings, respectively. The furan ring is almost perpendicular to the C12—C17 phenyl ring, with a dihedral angle of 94.0 (3)°.

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).

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
[Figure 1] Fig. 1. A view of the molecule of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 60% probability level.
rac-3-{4-[(Furan-2-ylmethylidene)amino]-3-methyl-5-sulfanylidene- 4,5-dihydro-1H-1,2,4-triazol-1-yl}-1,3-diphenylpropan-1-one top
Crystal data top
C23H20N4O2SF(000) = 872
Mr = 416.50Dx = 1.307 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7435 reflections
a = 8.154 (3) Åθ = 1.7–27.9°
b = 21.194 (6) ŵ = 0.18 mm1
c = 12.878 (4) ÅT = 113 K
β = 107.965 (5)°Prism, colorless
V = 2117.0 (12) Å30.24 × 0.20 × 0.12 mm
Z = 4
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
5030 independent reflections
Radiation source: rotating anode4229 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.043
Detector resolution: 14.63 pixels mm-1θmax = 27.9°, θmin = 1.9°
φ and ω scansh = 1010
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 2727
Tmin = 0.958, Tmax = 0.979l = 1616
26979 measured reflections
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0597P)2 + 0.0507P]
where P = (Fo2 + 2Fc2)/3
5030 reflections(Δ/σ)max = 0.001
272 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C23H20N4O2SV = 2117.0 (12) Å3
Mr = 416.50Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.154 (3) ŵ = 0.18 mm1
b = 21.194 (6) ÅT = 113 K
c = 12.878 (4) Å0.24 × 0.20 × 0.12 mm
β = 107.965 (5)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
5030 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
4229 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.979Rint = 0.043
26979 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.07Δρmax = 0.33 e Å3
5030 reflectionsΔρmin = 0.18 e Å3
272 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
S11.09278 (4)0.678722 (17)0.64588 (3)0.03095 (11)
O10.74128 (14)0.76825 (5)0.75402 (7)0.0366 (2)
O20.80256 (13)0.49556 (5)0.33988 (7)0.0370 (2)
N10.89702 (13)0.64352 (5)0.77200 (8)0.0210 (2)
N20.76948 (13)0.60222 (5)0.77821 (8)0.0258 (2)
N30.82733 (13)0.59160 (5)0.62302 (8)0.0231 (2)
N40.81208 (14)0.55961 (5)0.52572 (8)0.0287 (3)
C10.93901 (15)0.63862 (6)0.67870 (9)0.0215 (3)
C20.73025 (17)0.57115 (6)0.68692 (10)0.0265 (3)
C30.98664 (16)0.68280 (6)0.86642 (9)0.0231 (3)
H31.04210.71870.83960.028*
C40.85808 (17)0.71013 (6)0.91857 (10)0.0272 (3)
H4A0.79420.67510.93940.033*
H4B0.92190.73290.98610.033*
C50.73023 (17)0.75493 (6)0.84367 (10)0.0265 (3)
C60.59252 (16)0.78340 (6)0.88329 (10)0.0254 (3)
C70.45618 (19)0.81411 (6)0.80761 (12)0.0339 (3)
H70.45090.81540.73290.041*
C80.3287 (2)0.84270 (7)0.84094 (13)0.0431 (4)
H80.23490.86300.78890.052*
C90.3374 (2)0.84195 (7)0.95004 (13)0.0414 (4)
H90.25090.86250.97290.050*
C100.47170 (19)0.81126 (6)1.02590 (12)0.0327 (3)
H100.47660.81041.10050.039*
C110.59897 (17)0.78178 (6)0.99299 (10)0.0275 (3)
H110.69070.76051.04500.033*
C121.12820 (16)0.64429 (6)0.94503 (9)0.0234 (3)
C131.08906 (17)0.59523 (6)1.00540 (10)0.0288 (3)
H130.97220.58701.00010.035*
C141.21854 (18)0.55835 (7)1.07314 (11)0.0325 (3)
H141.19040.52491.11370.039*
C151.38920 (18)0.57036 (7)1.08172 (11)0.0373 (3)
H151.47830.54521.12810.045*
C161.42945 (18)0.61911 (7)1.02258 (12)0.0401 (4)
H161.54660.62741.02870.048*
C171.30023 (17)0.65601 (7)0.95437 (11)0.0314 (3)
H171.32910.68940.91390.038*
C180.86294 (17)0.58860 (7)0.45364 (10)0.0296 (3)
H180.90780.63020.46720.036*
C190.85153 (17)0.55772 (7)0.35217 (10)0.0309 (3)
C200.87864 (18)0.57953 (8)0.26002 (11)0.0385 (3)
H200.91370.62090.24770.046*
C210.84408 (19)0.52813 (8)0.18528 (12)0.0420 (4)
H210.85140.52840.11310.050*
C220.79925 (19)0.47929 (8)0.23657 (11)0.0410 (4)
H220.76910.43870.20530.049*
C230.5960 (2)0.52161 (7)0.65264 (11)0.0430 (4)
H23A0.55050.51220.71300.064*
H23B0.64650.48330.63260.064*
H23C0.50230.53660.58960.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02698 (19)0.0442 (2)0.02233 (18)0.00676 (14)0.00865 (14)0.00319 (14)
O10.0485 (6)0.0389 (5)0.0253 (5)0.0118 (5)0.0157 (5)0.0049 (4)
O20.0429 (6)0.0387 (5)0.0242 (5)0.0133 (5)0.0029 (4)0.0078 (4)
N10.0226 (5)0.0225 (5)0.0178 (5)0.0028 (4)0.0064 (4)0.0018 (4)
N20.0259 (6)0.0297 (6)0.0211 (5)0.0072 (4)0.0063 (4)0.0013 (4)
N30.0281 (6)0.0235 (5)0.0160 (5)0.0001 (4)0.0043 (4)0.0017 (4)
N40.0341 (6)0.0309 (6)0.0172 (5)0.0061 (5)0.0023 (4)0.0055 (4)
C10.0229 (6)0.0241 (6)0.0166 (6)0.0029 (5)0.0046 (5)0.0011 (5)
C20.0301 (7)0.0274 (6)0.0192 (6)0.0050 (5)0.0035 (5)0.0027 (5)
C30.0271 (7)0.0229 (6)0.0183 (6)0.0037 (5)0.0055 (5)0.0036 (5)
C40.0339 (7)0.0273 (7)0.0195 (6)0.0040 (6)0.0069 (5)0.0033 (5)
C50.0323 (7)0.0236 (6)0.0222 (6)0.0004 (5)0.0063 (5)0.0041 (5)
C60.0275 (7)0.0218 (6)0.0263 (6)0.0025 (5)0.0074 (5)0.0016 (5)
C70.0347 (8)0.0358 (7)0.0308 (7)0.0035 (6)0.0097 (6)0.0065 (6)
C80.0360 (8)0.0490 (9)0.0460 (9)0.0126 (7)0.0153 (7)0.0151 (7)
C90.0392 (9)0.0420 (8)0.0509 (9)0.0085 (7)0.0255 (8)0.0075 (7)
C100.0379 (8)0.0320 (7)0.0327 (7)0.0012 (6)0.0175 (6)0.0010 (6)
C110.0304 (7)0.0251 (6)0.0263 (6)0.0038 (5)0.0078 (5)0.0023 (5)
C120.0257 (6)0.0235 (6)0.0197 (6)0.0018 (5)0.0051 (5)0.0053 (5)
C130.0259 (7)0.0316 (7)0.0276 (7)0.0014 (5)0.0064 (5)0.0006 (5)
C140.0349 (8)0.0333 (7)0.0270 (7)0.0004 (6)0.0059 (6)0.0043 (6)
C150.0300 (7)0.0457 (8)0.0307 (7)0.0070 (6)0.0013 (6)0.0049 (6)
C160.0231 (7)0.0558 (10)0.0374 (8)0.0030 (7)0.0035 (6)0.0030 (7)
C170.0293 (7)0.0355 (7)0.0268 (7)0.0071 (6)0.0052 (6)0.0001 (6)
C180.0312 (7)0.0346 (7)0.0203 (6)0.0082 (6)0.0038 (5)0.0023 (5)
C190.0271 (7)0.0390 (7)0.0233 (6)0.0104 (6)0.0026 (5)0.0044 (6)
C200.0343 (8)0.0556 (9)0.0252 (7)0.0017 (7)0.0086 (6)0.0073 (6)
C210.0342 (8)0.0678 (11)0.0231 (7)0.0116 (8)0.0073 (6)0.0102 (7)
C220.0372 (8)0.0515 (9)0.0266 (7)0.0192 (7)0.0012 (6)0.0157 (7)
C230.0523 (10)0.0433 (9)0.0259 (7)0.0241 (7)0.0012 (7)0.0018 (6)
Geometric parameters (Å, º) top
S1—C11.6734 (13)C9—H90.9500
O1—C51.2185 (15)C10—C111.3851 (19)
O2—C221.3666 (16)C10—H100.9500
O2—C191.3715 (18)C11—H110.9500
N1—C11.3511 (15)C12—C171.3927 (18)
N1—N21.3803 (14)C12—C131.3930 (18)
N1—C31.4688 (15)C13—C141.3852 (19)
N2—C21.2984 (16)C13—H130.9500
N3—C21.3760 (16)C14—C151.385 (2)
N3—C11.3906 (15)C14—H140.9500
N3—N41.3961 (14)C15—C161.382 (2)
N4—C181.2840 (17)C15—H150.9500
C2—C231.4823 (18)C16—C171.387 (2)
C3—C121.5174 (17)C16—H160.9500
C3—C41.5232 (17)C17—H170.9500
C3—H31.0000C18—C191.4386 (18)
C4—C51.5160 (18)C18—H180.9500
C4—H4A0.9900C19—C201.354 (2)
C4—H4B0.9900C20—C211.423 (2)
C5—C61.4961 (18)C20—H200.9500
C6—C71.3932 (19)C21—C221.338 (2)
C6—C111.3978 (17)C21—H210.9500
C7—C81.381 (2)C22—H220.9500
C7—H70.9500C23—H23A0.9800
C8—C91.385 (2)C23—H23B0.9800
C8—H80.9500C23—H23C0.9800
C9—C101.385 (2)
C22—O2—C19105.81 (11)C11—C10—H10120.0
C1—N1—N2113.88 (10)C10—C11—C6120.00 (13)
C1—N1—C3125.58 (10)C10—C11—H11120.0
N2—N1—C3120.19 (9)C6—C11—H11120.0
C2—N2—N1104.40 (10)C17—C12—C13118.88 (12)
C2—N3—C1108.86 (10)C17—C12—C3120.02 (11)
C2—N3—N4118.39 (10)C13—C12—C3121.05 (11)
C1—N3—N4132.36 (10)C14—C13—C12120.76 (13)
C18—N4—N3117.20 (11)C14—C13—H13119.6
N1—C1—N3102.03 (10)C12—C13—H13119.6
N1—C1—S1126.93 (9)C15—C14—C13119.89 (13)
N3—C1—S1131.01 (9)C15—C14—H14120.1
N2—C2—N3110.81 (11)C13—C14—H14120.1
N2—C2—C23125.59 (12)C16—C15—C14119.81 (13)
N3—C2—C23123.58 (11)C16—C15—H15120.1
N1—C3—C12109.22 (9)C14—C15—H15120.1
N1—C3—C4110.25 (10)C15—C16—C17120.51 (13)
C12—C3—C4113.31 (10)C15—C16—H16119.7
N1—C3—H3108.0C17—C16—H16119.7
C12—C3—H3108.0C16—C17—C12120.16 (13)
C4—C3—H3108.0C16—C17—H17119.9
C5—C4—C3112.91 (10)C12—C17—H17119.9
C5—C4—H4A109.0N4—C18—C19119.61 (13)
C3—C4—H4A109.0N4—C18—H18120.2
C5—C4—H4B109.0C19—C18—H18120.2
C3—C4—H4B109.0C20—C19—O2110.32 (12)
H4A—C4—H4B107.8C20—C19—C18131.19 (14)
O1—C5—C6120.81 (12)O2—C19—C18118.48 (12)
O1—C5—C4120.71 (12)C19—C20—C21106.23 (14)
C6—C5—C4118.47 (11)C19—C20—H20126.9
C7—C6—C11119.45 (12)C21—C20—H20126.9
C7—C6—C5118.08 (11)C22—C21—C20106.60 (13)
C11—C6—C5122.44 (12)C22—C21—H21126.7
C8—C7—C6120.15 (13)C20—C21—H21126.7
C8—C7—H7119.9C21—C22—O2111.03 (13)
C6—C7—H7119.9C21—C22—H22124.5
C7—C8—C9120.18 (14)O2—C22—H22124.5
C7—C8—H8119.9C2—C23—H23A109.5
C9—C8—H8119.9C2—C23—H23B109.5
C10—C9—C8120.17 (13)H23A—C23—H23B109.5
C10—C9—H9119.9C2—C23—H23C109.5
C8—C9—H9119.9H23A—C23—H23C109.5
C9—C10—C11120.03 (13)H23B—C23—H23C109.5
C9—C10—H10120.0
C1—N1—N2—C20.35 (13)C11—C6—C7—C80.0 (2)
C3—N1—N2—C2173.97 (11)C5—C6—C7—C8178.09 (13)
C2—N3—N4—C18160.90 (12)C6—C7—C8—C91.1 (2)
C1—N3—N4—C1827.24 (19)C7—C8—C9—C101.5 (2)
N2—N1—C1—N30.93 (13)C8—C9—C10—C110.7 (2)
C3—N1—C1—N3174.15 (10)C9—C10—C11—C60.5 (2)
N2—N1—C1—S1177.18 (9)C7—C6—C11—C100.84 (19)
C3—N1—C1—S13.96 (17)C5—C6—C11—C10177.21 (12)
C2—N3—C1—N11.14 (13)N1—C3—C12—C17106.97 (13)
N4—N3—C1—N1173.59 (11)C4—C3—C12—C17129.70 (12)
C2—N3—C1—S1176.86 (10)N1—C3—C12—C1370.35 (14)
N4—N3—C1—S14.4 (2)C4—C3—C12—C1352.98 (15)
N1—N2—C2—N30.43 (14)C17—C12—C13—C140.41 (18)
N1—N2—C2—C23178.64 (13)C3—C12—C13—C14176.94 (11)
C1—N3—C2—N21.04 (15)C12—C13—C14—C150.3 (2)
N4—N3—C2—N2174.70 (10)C13—C14—C15—C160.0 (2)
C1—N3—C2—C23179.29 (12)C14—C15—C16—C170.2 (2)
N4—N3—C2—C237.05 (18)C15—C16—C17—C120.1 (2)
C1—N1—C3—C1290.83 (13)C13—C12—C17—C160.19 (19)
N2—N1—C3—C1281.99 (13)C3—C12—C17—C16177.19 (12)
C1—N1—C3—C4144.04 (11)N3—N4—C18—C19179.51 (11)
N2—N1—C3—C443.14 (14)C22—O2—C19—C200.25 (15)
N1—C3—C4—C564.25 (13)C22—O2—C19—C18178.72 (11)
C12—C3—C4—C5172.98 (10)N4—C18—C19—C20172.22 (14)
C3—C4—C5—O13.40 (17)N4—C18—C19—O26.51 (19)
C3—C4—C5—C6177.83 (11)O2—C19—C20—C210.22 (16)
O1—C5—C6—C713.79 (19)C18—C19—C20—C21178.59 (14)
C4—C5—C6—C7167.44 (12)C19—C20—C21—C220.10 (16)
O1—C5—C6—C11164.29 (12)C20—C21—C22—O20.06 (17)
C4—C5—C6—C1114.49 (18)C19—O2—C22—C210.19 (15)

Experimental details

Crystal data
Chemical formulaC23H20N4O2S
Mr416.50
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)8.154 (3), 21.194 (6), 12.878 (4)
β (°) 107.965 (5)
V3)2117.0 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.24 × 0.20 × 0.12
Data collection
DiffractometerRigaku Saturn CCD area-detector
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.958, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
26979, 5030, 4229
Rint0.043
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.106, 1.07
No. of reflections5030
No. of parameters272
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.18

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

 

Acknowledgements

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

References

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First citationFun, H.-K., Chantrapromma, S., Sujith, K. V. & Kalluraya, B. (2009). Acta Cryst. E65, o495–o496.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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First citationRigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.  Google Scholar
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First citationZhao, 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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