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ISSN: 2056-9890

6-(2-Methyl­phen­yl)-3-(3,4,5-tri­meth­oxy­phen­yl)-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole

aDepartment of Chemistry, College of Science, Tianjin University, Tianjin 300072, People's Republic of China, bDepartment of Biology and Environment alTechnology, Guiyang College, Guiyang 550005, People's Republic of China, and cSchool of Chemistry and Environmental Sciences, Guizhou University for Nationalities, Guiyang 550025, People's Republic of China
*Correspondence e-mail: haitangdu@gz139.com.cn

(Received 2 July 2008; accepted 4 July 2008; online 12 July 2008)

In the mol­ecule of the title compound, C19H18N4O3S, the planar central heterocylic ring system is oriented with respect to the trimethoxy­phenyl and 2-methyl­phenyl rings at dihedral angles of 4.43 (3) and 4.32 (3)°, respectively. The dihedral angle between the two benzene rings is 7.65 (4)°. In the crystal structure, inter­molecular C—H⋯N hydrogen bonds link the mol­ecules into centrosymmetric R22(18) dimers. These dimers are connected via a C—H⋯π contact between the 2-methyl­phenyl and trimethoxy­phenyl rings, and a ππ contact between the thia­diazole and trimethoxy­phenyl rings [interplanar distance 3.51 Å, dihedral angles 4.17(4)°]. An intramolecular C—H⋯N hydrogen bond is also present.

Related literature

For general background, see: Karabasanagouda et al. (2007[Karabasanagouda, T., Adhikari, A. V. & Shetty, S. N. (2007). Eur. J. Med. Chem. 42, 521-529.]); Mathew et al. (2007[Mathew, V., Keshavayya, J., Vaidya, V. P. & Giles, D. (2007). Eur. J. Med. Chem. 42, 823-840.]). For ring motif details, see: Bernstein et al. (1995[Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18N4O3S

  • Mr = 382.43

  • Monoclinic, P 21 /c

  • a = 7.5108 (15) Å

  • b = 15.950 (3) Å

  • c = 14.096 (3) Å

  • β = 91.88 (3)°

  • V = 1687.7 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 113 (2) K

  • 0.24 × 0.20 × 0.16 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC. (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.923, Tmax = 0.965

  • 11990 measured reflections

  • 3984 independent reflections

  • 3408 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.108

  • S = 1.07

  • 3984 reflections

  • 248 parameters

  • H-atom parameters constrained

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯N4 0.95 2.45 3.127 (3) 128
C7—H7C⋯N2i 0.98 2.62 3.524 (3) 154
C19—H19B⋯CgAii 0.98 2.90 3.808 (3) 155
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y, -z. CgA is the centroid of the trimethoxyphenyl ring.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC. (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005[Rigaku/MSC. (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); 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.]) and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXTL and PLATON.

Supporting information


Comment top

1,2,4-Triazole and 1,3,4-thiadiazole represent one of the most biologically active classes of compounds, possessing a wide spectrum of activities. Various substituted 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles are associated with diverse pharmacological activities such as antimicrobial (Karabasanagouda et al., 2007) and anti-inflammatory activity (Mathew et al., 2007). We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1) the bond lengths and angles are within normal ranges. Rings A (C1-C6), B (N1-N3/C10/C11), C (S1/N3/N4/C11/C12) and D (C13-C18) are, of course, planar, and the dihedral angles between them are A/B = 4.63 (4)°, A/C = 4.08 (3)°, A/D = 7.65 (4)°, B/C = 0.94 (3)°, B/D = 4.59 (4)° and C/D = 4.25 (4)°. So, rings B and C are nearly coplanar. The coplanar ring system is oriented with respect to rings A and D at dihedral angles of 4.43 (3)° and 4.32 (3)°, respectively. The intra- molecular C-H···N hydrogen bond (Table 1) results in the formation of a planar six-membered ring E (N3/N4/C1/C2/C10/H2), in which it is oriented with respect to the other rings at dihedral angles of A/E = 3.24 (4)°, B/E = 1.39 (3)°, C/E = 1.03 (3)° and D/E = 5.25 (4)°. So, rings A, B, C and E are also nearly coplanar.

In the crystal structure, intermolecular weak C-H···N hydrogen bonds (Table 1) link the molecules to form a R22(18) ring motif (Fig. 2) (Bernstein et al., 1995), in which they may be effective in the stabilization of the structure. The C—H···π contact (Table 1) between the 2-methylphenyl and trimethoxyphenyl rings and a ππ contact between the thiadiazole and trimethoxyphenyl rings CgC···CgAi [symmetry code: (i) 1 - x, 1 - y, 1 - z] further stabilize the structure, with centroid-centroid distance of 3.506 (1) Å.

Related literature top

For general background, see: Karabasanagouda et al. (2007); Mathew et al. (2007). For ring motif details, see: Bernstein et al. (1995). CgA is the centroid of the C1–C6 ring.

Experimental top

For the preparation of the title compound, 4-amino-5-(3,4,5-trimethoxyphenyl) -4H-1,2,4-triazole-3-thiol (0.01 M) and 2-methylbenzoic acid (0.01 M) were dissolved in dry phosphorous oxychloride (10 ml). The resulted solution was further heated under reflux for 7 h. The reaction mixture was cooled to room temperature and the mixture was gradually poured onto crushed ice with stirring. Finally, powdered potassium carbonate and the required amount of solid potassium hydroxide were added until the pH of the mixture was raised to 8, to remove the excess of phosphorous oxychloride. The mixture was allowed to stand overnight and the solid was separated. It was filtered, washed with cold water, and then dried. Crystals suitable for X-ray analysis were obtained by the recrystallization of the solid residue from a mixture of N,N-dimethyl- formamide/ethanol (1:1) by slow evaporation at room temperature.

Refinement top

H atoms were positioned geometrically, with C-H = 0.95 and 0.98 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for aromatic H atoms.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalStructure (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) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A partial packing diagram of the title compound [symmetry code: (') -x, -y, -z]. Hydrogen bonds are shown as dashed lines.
6-(2-Methylphenyl)-3-(3,4,5-trimethoxyphenyl)-1,2,4- triazolo[3,4-b][1,3,4]thiadiazole top
Crystal data top
C19H18N4O3SF(000) = 800
Mr = 382.43Dx = 1.505 Mg m3
Monoclinic, P21/cMelting point: 435 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.5108 (15) ÅCell parameters from 4684 reflections
b = 15.950 (3) Åθ = 1.9–27.9°
c = 14.096 (3) ŵ = 0.22 mm1
β = 91.88 (3)°T = 113 K
V = 1687.7 (6) Å3Prism, colorless
Z = 40.24 × 0.20 × 0.16 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
3984 independent reflections
Radiation source: rotating anode3408 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.031
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 1.9°
ω and ϕ scansh = 99
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 2020
Tmin = 0.923, Tmax = 0.965l = 1718
11990 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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0664P)2 + 0.1888P]
where P = (Fo2 + 2Fc2)/3
3984 reflections(Δ/σ)max = 0.002
248 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C19H18N4O3SV = 1687.7 (6) Å3
Mr = 382.43Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.5108 (15) ŵ = 0.22 mm1
b = 15.950 (3) ÅT = 113 K
c = 14.096 (3) Å0.24 × 0.20 × 0.16 mm
β = 91.88 (3)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
3984 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
3408 reflections with I > 2σ(I)
Tmin = 0.923, Tmax = 0.965Rint = 0.031
11990 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 1.07Δρmax = 0.39 e Å3
3984 reflectionsΔρmin = 0.35 e Å3
248 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 > 2sigma(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
S10.45611 (5)0.68554 (2)0.69693 (2)0.02005 (12)
O10.04396 (14)0.40664 (6)0.30838 (7)0.0227 (2)
O20.03955 (14)0.24866 (6)0.34593 (7)0.0223 (2)
O30.17803 (14)0.18588 (6)0.51532 (7)0.0209 (2)
N10.43365 (17)0.44321 (7)0.69492 (9)0.0208 (3)
N20.48819 (18)0.51377 (8)0.74703 (9)0.0226 (3)
N30.36258 (15)0.55345 (7)0.61030 (8)0.0156 (2)
N40.31020 (15)0.61420 (7)0.54614 (8)0.0164 (2)
C10.27851 (18)0.41101 (8)0.54193 (10)0.0162 (3)
C20.20134 (19)0.44117 (8)0.45750 (10)0.0176 (3)
H20.20180.49950.44390.021*
C30.12374 (18)0.38475 (9)0.39346 (10)0.0173 (3)
C40.12199 (18)0.29857 (8)0.41238 (10)0.0170 (3)
C50.19617 (18)0.26966 (8)0.49906 (10)0.0169 (3)
C60.27654 (18)0.32539 (8)0.56254 (10)0.0174 (3)
H60.33030.30530.62010.021*
C70.0480 (2)0.49299 (9)0.28278 (11)0.0232 (3)
H7A0.00990.52630.33140.035*
H7B0.01520.50090.22150.035*
H7C0.17200.51120.27780.035*
C80.1222 (2)0.17048 (9)0.32363 (12)0.0276 (4)
H8A0.25130.17500.33490.041*
H8B0.09680.15680.25680.041*
H8C0.07510.12620.36390.041*
C90.2468 (2)0.15402 (9)0.60340 (11)0.0247 (3)
H9A0.37560.16390.60830.037*
H9B0.22320.09370.60690.037*
H9C0.18900.18260.65570.037*
C100.35879 (18)0.46709 (8)0.61313 (10)0.0164 (3)
C110.44294 (18)0.57788 (9)0.69380 (10)0.0182 (3)
C120.35200 (18)0.68710 (8)0.58207 (9)0.0159 (3)
C130.32100 (18)0.76838 (8)0.53561 (10)0.0167 (3)
C140.3639 (2)0.84107 (9)0.58780 (11)0.0212 (3)
H140.41010.83570.65100.025*
C150.3405 (2)0.92022 (9)0.54955 (11)0.0240 (3)
H150.37240.96860.58550.029*
C160.2700 (2)0.92787 (9)0.45800 (11)0.0245 (3)
H160.25210.98190.43090.029*
C170.22563 (19)0.85687 (9)0.40588 (11)0.0210 (3)
H170.17620.86340.34340.025*
C180.25090 (18)0.77609 (9)0.44191 (10)0.0174 (3)
C190.2042 (2)0.70232 (9)0.37935 (10)0.0206 (3)
H19A0.16330.72240.31660.031*
H19B0.10930.66970.40790.031*
H19C0.30960.66690.37270.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0259 (2)0.01750 (18)0.01647 (19)0.00076 (13)0.00384 (14)0.00149 (12)
O10.0347 (6)0.0148 (5)0.0181 (5)0.0021 (4)0.0071 (4)0.0011 (4)
O20.0258 (6)0.0165 (5)0.0242 (6)0.0014 (4)0.0056 (4)0.0036 (4)
O30.0278 (6)0.0142 (5)0.0203 (5)0.0019 (4)0.0035 (4)0.0032 (4)
N10.0244 (7)0.0189 (6)0.0190 (6)0.0012 (5)0.0023 (5)0.0002 (5)
N20.0287 (7)0.0196 (6)0.0193 (6)0.0012 (5)0.0038 (5)0.0006 (5)
N30.0173 (6)0.0158 (5)0.0136 (5)0.0000 (4)0.0010 (4)0.0005 (4)
N40.0182 (6)0.0149 (5)0.0160 (6)0.0005 (4)0.0002 (4)0.0024 (4)
C10.0154 (6)0.0170 (6)0.0164 (7)0.0007 (5)0.0026 (5)0.0006 (5)
C20.0202 (7)0.0150 (6)0.0177 (7)0.0015 (5)0.0012 (5)0.0004 (5)
C30.0200 (7)0.0179 (7)0.0140 (6)0.0031 (5)0.0005 (5)0.0003 (5)
C40.0171 (7)0.0155 (6)0.0184 (7)0.0001 (5)0.0003 (5)0.0022 (5)
C50.0167 (7)0.0142 (6)0.0199 (7)0.0010 (5)0.0034 (5)0.0014 (5)
C60.0168 (7)0.0190 (7)0.0165 (7)0.0019 (5)0.0005 (5)0.0020 (5)
C70.0316 (8)0.0161 (7)0.0217 (7)0.0028 (6)0.0042 (6)0.0037 (5)
C80.0387 (9)0.0170 (7)0.0265 (8)0.0034 (6)0.0065 (7)0.0061 (6)
C90.0335 (9)0.0177 (7)0.0227 (8)0.0002 (6)0.0037 (6)0.0058 (6)
C100.0169 (7)0.0146 (6)0.0177 (7)0.0008 (5)0.0016 (5)0.0014 (5)
C110.0196 (7)0.0196 (6)0.0154 (7)0.0006 (5)0.0010 (5)0.0013 (5)
C120.0147 (6)0.0180 (7)0.0149 (7)0.0003 (5)0.0002 (5)0.0013 (5)
C130.0161 (7)0.0163 (6)0.0176 (7)0.0005 (5)0.0006 (5)0.0000 (5)
C140.0233 (7)0.0198 (7)0.0204 (7)0.0001 (6)0.0018 (6)0.0023 (6)
C150.0287 (8)0.0161 (6)0.0271 (8)0.0007 (6)0.0012 (6)0.0030 (6)
C160.0297 (8)0.0168 (7)0.0270 (8)0.0013 (6)0.0005 (6)0.0025 (6)
C170.0218 (7)0.0216 (7)0.0198 (7)0.0011 (6)0.0004 (5)0.0019 (5)
C180.0163 (7)0.0190 (7)0.0169 (7)0.0004 (5)0.0015 (5)0.0003 (5)
C190.0245 (8)0.0200 (7)0.0172 (7)0.0012 (6)0.0015 (5)0.0009 (5)
Geometric parameters (Å, º) top
S1—C111.7205 (15)C7—H7A0.9800
S1—C121.7749 (15)C7—H7B0.9800
O1—C31.3682 (17)C7—H7C0.9800
O1—C71.4244 (16)C8—H8A0.9800
O2—C41.3625 (16)C8—H8B0.9800
O2—C81.4325 (17)C8—H8C0.9800
O3—C51.3633 (16)C9—H9A0.9800
O3—C91.4229 (17)C9—H9B0.9800
N1—C101.3221 (18)C9—H9C0.9800
N1—N21.3978 (17)C12—C131.4677 (19)
N2—C111.3067 (18)C13—C141.4048 (19)
N3—C111.3619 (18)C13—C181.411 (2)
N3—N41.3742 (16)C14—C151.382 (2)
N3—C101.3783 (17)C14—H140.9500
N4—C121.3026 (17)C15—C161.384 (2)
C1—C21.392 (2)C15—H150.9500
C1—C61.3964 (19)C16—C171.385 (2)
C1—C101.4600 (19)C16—H160.9500
C2—C31.3893 (19)C17—C181.3956 (19)
C2—H20.9500C17—H170.9500
C3—C41.4003 (19)C18—C191.5050 (19)
C4—C51.404 (2)C19—H19A0.9800
C5—C61.3855 (19)C19—H19B0.9800
C6—H60.9500C19—H19C0.9800
C11—S1—C1288.13 (6)O3—C9—H9A109.5
C3—O1—C7117.15 (11)O3—C9—H9B109.5
C4—O2—C8117.97 (11)H9A—C9—H9B109.5
C5—O3—C9117.47 (11)O3—C9—H9C109.5
C10—N1—N2109.59 (11)H9A—C9—H9C109.5
C11—N2—N1105.19 (12)H9B—C9—H9C109.5
C11—N3—N4118.44 (11)N1—C10—N3107.73 (12)
C11—N3—C10105.66 (11)N1—C10—C1125.26 (12)
N4—N3—C10135.89 (12)N3—C10—C1126.93 (12)
C12—N4—N3108.26 (11)N2—C11—N3111.83 (13)
C2—C1—C6120.59 (13)N2—C11—S1138.82 (11)
C2—C1—C10121.79 (12)N3—C11—S1109.35 (10)
C6—C1—C10117.59 (12)N4—C12—C13125.61 (13)
C3—C2—C1119.05 (13)N4—C12—S1115.82 (10)
C3—C2—H2120.5C13—C12—S1118.57 (10)
C1—C2—H2120.5C14—C13—C18119.37 (13)
O1—C3—C2124.52 (12)C14—C13—C12117.71 (13)
O1—C3—C4114.26 (12)C18—C13—C12122.93 (12)
C2—C3—C4121.23 (13)C15—C14—C13121.71 (14)
O2—C4—C3116.72 (12)C15—C14—H14119.1
O2—C4—C5124.38 (12)C13—C14—H14119.1
C3—C4—C5118.83 (12)C14—C15—C16118.96 (14)
O3—C5—C6124.34 (13)C14—C15—H15120.5
O3—C5—C4115.42 (12)C16—C15—H15120.5
C6—C5—C4120.22 (12)C15—C16—C17120.04 (14)
C5—C6—C1120.03 (13)C15—C16—H16120.0
C5—C6—H6120.0C17—C16—H16120.0
C1—C6—H6120.0C16—C17—C18122.30 (14)
O1—C7—H7A109.5C16—C17—H17118.8
O1—C7—H7B109.5C18—C17—H17118.8
H7A—C7—H7B109.5C17—C18—C13117.60 (13)
O1—C7—H7C109.5C17—C18—C19118.83 (13)
H7A—C7—H7C109.5C13—C18—C19123.57 (12)
H7B—C7—H7C109.5C18—C19—H19A109.5
O2—C8—H8A109.5C18—C19—H19B109.5
O2—C8—H8B109.5H19A—C19—H19B109.5
H8A—C8—H8B109.5C18—C19—H19C109.5
O2—C8—H8C109.5H19A—C19—H19C109.5
H8A—C8—H8C109.5H19B—C19—H19C109.5
H8B—C8—H8C109.5
C10—N1—N2—C110.13 (16)C2—C1—C10—N1179.68 (13)
C11—N3—N4—C120.04 (16)C6—C1—C10—N11.6 (2)
C10—N3—N4—C12178.51 (15)C2—C1—C10—N33.3 (2)
C6—C1—C2—C30.6 (2)C6—C1—C10—N3174.73 (13)
C10—C1—C2—C3178.64 (13)N1—N2—C11—N30.07 (16)
C7—O1—C3—C22.7 (2)N1—N2—C11—S1179.34 (13)
C7—O1—C3—C4177.29 (12)N4—N3—C11—N2178.90 (12)
C1—C2—C3—O1179.99 (13)C10—N3—C11—N20.01 (16)
C1—C2—C3—C40.0 (2)N4—N3—C11—S10.58 (15)
C8—O2—C4—C3138.95 (14)C10—N3—C11—S1179.48 (9)
C8—O2—C4—C544.2 (2)C12—S1—C11—N2178.60 (18)
O1—C3—C4—O21.28 (18)C12—S1—C11—N30.68 (10)
C2—C3—C4—O2178.74 (12)N3—N4—C12—C13179.15 (12)
O1—C3—C4—C5178.28 (12)N3—N4—C12—S10.53 (14)
C2—C3—C4—C51.7 (2)C11—S1—C12—N40.74 (11)
C9—O3—C5—C60.1 (2)C11—S1—C12—C13178.97 (11)
C9—O3—C5—C4178.32 (12)N4—C12—C13—C14175.74 (13)
O2—C4—C5—O31.3 (2)S1—C12—C13—C144.59 (17)
C3—C4—C5—O3175.43 (12)N4—C12—C13—C184.3 (2)
O2—C4—C5—C6179.60 (13)S1—C12—C13—C18175.39 (11)
C3—C4—C5—C62.9 (2)C18—C13—C14—C150.5 (2)
O3—C5—C6—C1175.88 (13)C12—C13—C14—C15179.46 (13)
C4—C5—C6—C12.2 (2)C13—C14—C15—C161.2 (2)
C2—C1—C6—C50.5 (2)C14—C15—C16—C170.6 (2)
C10—C1—C6—C5177.61 (12)C15—C16—C17—C180.7 (2)
N2—N1—C10—N30.13 (15)C16—C17—C18—C131.3 (2)
N2—N1—C10—C1177.07 (12)C16—C17—C18—C19178.14 (14)
C11—N3—C10—N10.09 (15)C14—C13—C18—C170.7 (2)
N4—N3—C10—N1178.69 (14)C12—C13—C18—C17179.32 (13)
C11—N3—C10—C1176.96 (13)C14—C13—C18—C19178.70 (13)
N4—N3—C10—C14.4 (3)C12—C13—C18—C191.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N40.952.453.127 (3)128
C7—H7C···N2i0.982.623.524 (3)154
C19—H19B···CgAii0.982.903.808 (3)155
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y, z.

Experimental details

Crystal data
Chemical formulaC19H18N4O3S
Mr382.43
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)7.5108 (15), 15.950 (3), 14.096 (3)
β (°) 91.88 (3)
V3)1687.7 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.24 × 0.20 × 0.16
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.923, 0.965
No. of measured, independent and
observed [I > 2σ(I)] reflections
11990, 3984, 3408
Rint0.031
(sin θ/λ)max1)0.657
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.108, 1.07
No. of reflections3984
No. of parameters248
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.39, 0.35

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalStructure (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N40.952.453.127 (3)128.00
C7—H7C···N2i0.982.623.524 (3)154.00
C19—H19B···CgAii0.982.8963.808 (3)155.30
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y, z.
 

Acknowledgements

The authors thank Guiyang College (grant No. 2008012) for financial support.

References

First citationBernstein, J., Davies, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationKarabasanagouda, T., Adhikari, A. V. & Shetty, S. N. (2007). Eur. J. Med. Chem. 42, 521–529.  Web of Science CrossRef PubMed CAS Google Scholar
First citationMathew, V., Keshavayya, J., Vaidya, V. P. & Giles, D. (2007). Eur. J. Med. Chem. 42, 823–840.  Web of Science CrossRef PubMed CAS Google Scholar
First citationRigaku/MSC. (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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