organic compounds
5-(4-Bromophenoxy)-1-methyl-3-methyl-1H-pyrazole-4-carbaldehyde-O-[(5-methoxy-1,3,4-thiadiazol-2-yl)-methyl]oxime
aCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, People's Republic of China
*Correspondence e-mail: gaofz2005@yahoo.com.cn, yjshi2001@yahoo.com.cn
In the title molecule, C16H16BrN5O3S, the 1,3,4-thiadiazole ring is situated under the benzene ring, forming a dihedral angle of 86.6 (2)°, and with an S⋯Cg (where Cg is the centroid of the benzene ring) distance of 3.312 (3) Å. The benzene and 1,3,4-thiadiazole rings form dihedral angles of 83.8 (3) and 57.7 (2)°, respectively, with the central pyrazole ring. In the absence of classical hydrogen bonds, the crystal packing is stabilized by a C—H⋯π interaction..
Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku, 2008); cell 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
10.1107/S1600536812042274/cv5348sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812042274/cv5348Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812042274/cv5348Isup3.cml
To a stirred solution of 1-methyl-3-methyl-5-(4-bromophenoxy)-1H-pyrazole -4-carbaldehyde oxime (3 mmol), and powdered potassium carbonate (9 mmol) in 30 ml of anhydrous acetonitrile, was added 2-chloromethyl-5-methoxy- 1,3,4-thiadiazole (4.2 mmol) at room temperature. The mixture was heated to reflux for 13 h. After removal of the solvent, the residue was separated by
on silica gel using a mixture of petroleum ether/ethyl acetate to obtain colourless crystals.All H atoms were placed in calculated positions, with C–H = 0.95–0.99 Å, and included in the final cycles of
using a riding model, with Uiso(H) = 1.2Ueq(C).Data collection: CrystalClear (Rigaku, 2008); cell
CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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).Fig. 1. The molecular structure of (I) showing the atomic numbering and 50% probabilty displacement ellipsoids. |
C16H16BrN5O3S | Z = 2 |
Mr = 438.31 | F(000) = 444 |
Triclinic, P1 | Dx = 1.622 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.732 (3) Å | Cell parameters from 3391 reflections |
b = 9.832 (2) Å | θ = 2.1–27.9° |
c = 11.166 (3) Å | µ = 2.43 mm−1 |
α = 64.55 (2)° | T = 113 K |
β = 69.62 (2)° | Prism, colourless |
γ = 75.33 (3)° | 0.20 × 0.18 × 0.12 mm |
V = 897.5 (4) Å3 |
Rigaku Saturn724 CCD diffractometer | 3175 independent reflections |
Radiation source: rotating anode | 2363 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.044 |
Detector resolution: 14.22 pixels mm-1 | θmax = 25.0°, θmin = 2.1° |
ω and ϕ scans | h = −11→11 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008) | k = −11→11 |
Tmin = 0.642, Tmax = 0.759 | l = −13→13 |
7729 measured reflections |
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.054 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.P)2] where P = (Fo2 + 2Fc2)/3 |
3175 reflections | (Δ/σ)max = 0.001 |
238 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
C16H16BrN5O3S | γ = 75.33 (3)° |
Mr = 438.31 | V = 897.5 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.732 (3) Å | Mo Kα radiation |
b = 9.832 (2) Å | µ = 2.43 mm−1 |
c = 11.166 (3) Å | T = 113 K |
α = 64.55 (2)° | 0.20 × 0.18 × 0.12 mm |
β = 69.62 (2)° |
Rigaku Saturn724 CCD diffractometer | 3175 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008) | 2363 reflections with I > 2σ(I) |
Tmin = 0.642, Tmax = 0.759 | Rint = 0.044 |
7729 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 0 restraints |
wR(F2) = 0.054 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.36 e Å−3 |
3175 reflections | Δρmin = −0.49 e Å−3 |
238 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.51369 (3) | 0.66558 (3) | 1.32176 (3) | 0.02651 (10) | |
S1 | 0.54286 (8) | 0.73735 (8) | 0.87231 (7) | 0.02150 (19) | |
O1 | 0.96309 (18) | 0.88211 (18) | 0.76885 (17) | 0.0166 (5) | |
O2 | 0.63830 (19) | 0.93453 (19) | 0.53541 (18) | 0.0202 (5) | |
O3 | 0.3297 (2) | 0.6561 (2) | 1.10298 (18) | 0.0291 (5) | |
N1 | 1.0439 (2) | 1.1205 (2) | 0.6791 (2) | 0.0157 (5) | |
N2 | 1.0308 (2) | 1.2623 (2) | 0.5802 (2) | 0.0173 (6) | |
N3 | 0.7358 (2) | 0.9392 (2) | 0.6035 (2) | 0.0166 (5) | |
N4 | 0.3648 (2) | 0.7120 (2) | 0.7625 (2) | 0.0196 (6) | |
N5 | 0.2883 (2) | 0.6764 (2) | 0.9015 (2) | 0.0202 (6) | |
C1 | 0.6530 (3) | 0.7382 (3) | 1.1473 (3) | 0.0174 (7) | |
C2 | 0.6437 (3) | 0.8902 (3) | 1.0675 (3) | 0.0161 (7) | |
H2 | 0.5676 | 0.9587 | 1.0999 | 0.019* | |
C3 | 0.7454 (3) | 0.9447 (3) | 0.9390 (3) | 0.0155 (7) | |
H3 | 0.7395 | 1.0497 | 0.8827 | 0.019* | |
C4 | 0.8547 (3) | 0.8423 (3) | 0.8958 (3) | 0.0143 (6) | |
C5 | 0.8662 (3) | 0.6893 (3) | 0.9768 (3) | 0.0168 (7) | |
H5 | 0.9440 | 0.6213 | 0.9455 | 0.020* | |
C6 | 0.7646 (3) | 0.6357 (3) | 1.1029 (3) | 0.0176 (7) | |
H6 | 0.7705 | 0.5305 | 1.1587 | 0.021* | |
C7 | 0.9571 (3) | 1.0319 (3) | 0.6821 (3) | 0.0144 (7) | |
C8 | 0.8804 (3) | 1.1148 (3) | 0.5847 (3) | 0.0114 (6) | |
C9 | 0.9324 (3) | 1.2589 (3) | 0.5235 (3) | 0.0150 (7) | |
C10 | 0.8892 (3) | 1.3946 (3) | 0.4084 (2) | 0.0211 (7) | |
H10A | 0.9228 | 1.4843 | 0.4016 | 0.032* | |
H10B | 0.7816 | 1.4105 | 0.4264 | 0.032* | |
H10C | 0.9350 | 1.3784 | 0.3216 | 0.032* | |
C11 | 1.1437 (3) | 1.0799 (3) | 0.7631 (3) | 0.0239 (7) | |
H11A | 1.1112 | 1.1413 | 0.8199 | 0.036* | |
H11B | 1.2437 | 1.0986 | 0.7032 | 0.036* | |
H11C | 1.1436 | 0.9721 | 0.8229 | 0.036* | |
C12 | 0.7799 (3) | 1.0706 (3) | 0.5427 (3) | 0.0153 (6) | |
H12 | 0.7448 | 1.1421 | 0.4664 | 0.018* | |
C13 | 0.5995 (3) | 0.7852 (3) | 0.5917 (3) | 0.0194 (7) | |
H13A | 0.6904 | 0.7119 | 0.5950 | 0.023* | |
H13B | 0.5533 | 0.7753 | 0.5301 | 0.023* | |
C14 | 0.4958 (3) | 0.7459 (3) | 0.7328 (3) | 0.0151 (6) | |
C15 | 0.3691 (3) | 0.6834 (3) | 0.9682 (3) | 0.0194 (7) | |
C16 | 0.1869 (3) | 0.6019 (3) | 1.1781 (3) | 0.0360 (9) | |
H16A | 0.1105 | 0.6772 | 1.1391 | 0.054* | |
H16B | 0.1657 | 0.5860 | 1.2754 | 0.054* | |
H16C | 0.1879 | 0.5058 | 1.1708 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.02695 (19) | 0.03281 (19) | 0.01571 (17) | −0.00625 (14) | −0.00270 (14) | −0.00650 (15) |
S1 | 0.0216 (4) | 0.0264 (4) | 0.0212 (4) | −0.0059 (4) | −0.0073 (3) | −0.0105 (4) |
O1 | 0.0170 (11) | 0.0132 (10) | 0.0140 (11) | 0.0018 (8) | −0.0045 (8) | −0.0019 (9) |
O2 | 0.0230 (12) | 0.0190 (11) | 0.0215 (11) | −0.0089 (9) | −0.0136 (9) | −0.0009 (10) |
O3 | 0.0335 (13) | 0.0366 (13) | 0.0201 (12) | −0.0128 (11) | −0.0003 (10) | −0.0140 (11) |
N1 | 0.0149 (14) | 0.0174 (13) | 0.0178 (13) | −0.0006 (11) | −0.0085 (11) | −0.0070 (11) |
N2 | 0.0196 (14) | 0.0154 (13) | 0.0160 (13) | −0.0016 (11) | −0.0063 (11) | −0.0044 (11) |
N3 | 0.0142 (13) | 0.0213 (13) | 0.0184 (13) | −0.0059 (11) | −0.0091 (11) | −0.0056 (12) |
N4 | 0.0185 (14) | 0.0196 (13) | 0.0202 (14) | −0.0064 (11) | −0.0067 (11) | −0.0036 (12) |
N5 | 0.0190 (15) | 0.0195 (14) | 0.0211 (14) | −0.0057 (11) | −0.0055 (11) | −0.0050 (12) |
C1 | 0.0212 (17) | 0.0228 (16) | 0.0088 (15) | −0.0060 (14) | −0.0058 (13) | −0.0034 (14) |
C2 | 0.0157 (16) | 0.0167 (15) | 0.0195 (17) | 0.0050 (13) | −0.0105 (13) | −0.0095 (14) |
C3 | 0.0175 (16) | 0.0106 (14) | 0.0180 (16) | 0.0011 (13) | −0.0096 (13) | −0.0030 (13) |
C4 | 0.0155 (16) | 0.0176 (15) | 0.0121 (15) | −0.0018 (13) | −0.0075 (12) | −0.0049 (13) |
C5 | 0.0168 (16) | 0.0161 (15) | 0.0170 (16) | 0.0052 (13) | −0.0087 (13) | −0.0066 (13) |
C6 | 0.0220 (17) | 0.0134 (15) | 0.0184 (16) | 0.0020 (13) | −0.0130 (13) | −0.0034 (14) |
C7 | 0.0130 (16) | 0.0143 (15) | 0.0139 (15) | −0.0015 (13) | −0.0012 (12) | −0.0057 (13) |
C8 | 0.0103 (16) | 0.0103 (14) | 0.0130 (15) | −0.0014 (12) | −0.0040 (12) | −0.0031 (13) |
C9 | 0.0132 (16) | 0.0184 (15) | 0.0110 (15) | 0.0002 (13) | −0.0023 (13) | −0.0054 (13) |
C10 | 0.0225 (17) | 0.0156 (15) | 0.0202 (17) | −0.0059 (13) | −0.0059 (14) | −0.0003 (14) |
C11 | 0.0274 (19) | 0.0275 (18) | 0.0245 (17) | −0.0033 (15) | −0.0169 (14) | −0.0091 (15) |
C12 | 0.0100 (16) | 0.0194 (16) | 0.0137 (16) | 0.0028 (13) | −0.0055 (12) | −0.0043 (14) |
C13 | 0.0216 (17) | 0.0196 (16) | 0.0213 (17) | −0.0060 (14) | −0.0097 (14) | −0.0067 (14) |
C14 | 0.0198 (17) | 0.0106 (14) | 0.0219 (17) | −0.0005 (13) | −0.0105 (13) | −0.0096 (13) |
C15 | 0.0218 (18) | 0.0133 (15) | 0.0204 (17) | −0.0033 (13) | −0.0021 (14) | −0.0061 (14) |
C16 | 0.034 (2) | 0.039 (2) | 0.0244 (19) | −0.0063 (17) | 0.0040 (16) | −0.0103 (17) |
Br1—C1 | 1.897 (2) | C3—H3 | 0.9500 |
S1—C15 | 1.730 (3) | C4—C5 | 1.381 (3) |
S1—C14 | 1.735 (3) | C5—C6 | 1.376 (3) |
O1—C7 | 1.371 (3) | C5—H5 | 0.9500 |
O1—C4 | 1.402 (3) | C6—H6 | 0.9500 |
O2—C13 | 1.420 (3) | C7—C8 | 1.378 (3) |
O2—N3 | 1.426 (3) | C8—C9 | 1.422 (3) |
O3—C15 | 1.337 (3) | C8—C12 | 1.442 (3) |
O3—C16 | 1.449 (3) | C9—C10 | 1.492 (3) |
N1—C7 | 1.342 (3) | C10—H10A | 0.9800 |
N1—N2 | 1.365 (3) | C10—H10B | 0.9800 |
N1—C11 | 1.448 (3) | C10—H10C | 0.9800 |
N2—C9 | 1.333 (3) | C11—H11A | 0.9800 |
N3—C12 | 1.279 (3) | C11—H11B | 0.9800 |
N4—C14 | 1.293 (3) | C11—H11C | 0.9800 |
N4—N5 | 1.395 (3) | C12—H12 | 0.9500 |
N5—C15 | 1.287 (3) | C13—C14 | 1.489 (3) |
C1—C2 | 1.370 (3) | C13—H13A | 0.9900 |
C1—C6 | 1.393 (3) | C13—H13B | 0.9900 |
C2—C3 | 1.395 (3) | C16—H16A | 0.9800 |
C2—H2 | 0.9500 | C16—H16B | 0.9800 |
C3—C4 | 1.376 (3) | C16—H16C | 0.9800 |
C15—S1—C14 | 85.62 (13) | N2—C9—C10 | 121.1 (2) |
C7—O1—C4 | 117.5 (2) | C8—C9—C10 | 127.0 (3) |
C13—O2—N3 | 109.17 (19) | C9—C10—H10A | 109.5 |
C15—O3—C16 | 114.5 (2) | C9—C10—H10B | 109.5 |
C7—N1—N2 | 111.0 (2) | H10A—C10—H10B | 109.5 |
C7—N1—C11 | 127.8 (2) | C9—C10—H10C | 109.5 |
N2—N1—C11 | 121.2 (2) | H10A—C10—H10C | 109.5 |
C9—N2—N1 | 105.0 (2) | H10B—C10—H10C | 109.5 |
C12—N3—O2 | 108.0 (2) | N1—C11—H11A | 109.5 |
C14—N4—N5 | 113.1 (2) | N1—C11—H11B | 109.5 |
C15—N5—N4 | 110.5 (2) | H11A—C11—H11B | 109.5 |
C2—C1—C6 | 121.0 (2) | N1—C11—H11C | 109.5 |
C2—C1—Br1 | 119.8 (2) | H11A—C11—H11C | 109.5 |
C6—C1—Br1 | 119.2 (2) | H11B—C11—H11C | 109.5 |
C1—C2—C3 | 120.2 (2) | N3—C12—C8 | 122.9 (3) |
C1—C2—H2 | 119.9 | N3—C12—H12 | 118.5 |
C3—C2—H2 | 119.9 | C8—C12—H12 | 118.5 |
C4—C3—C2 | 118.3 (2) | O2—C13—C14 | 112.9 (2) |
C4—C3—H3 | 120.8 | O2—C13—H13A | 109.0 |
C2—C3—H3 | 120.8 | C14—C13—H13A | 109.0 |
C3—C4—C5 | 121.7 (2) | O2—C13—H13B | 109.0 |
C3—C4—O1 | 124.0 (2) | C14—C13—H13B | 109.0 |
C5—C4—O1 | 114.3 (2) | H13A—C13—H13B | 107.8 |
C6—C5—C4 | 119.8 (3) | N4—C14—C13 | 123.1 (2) |
C6—C5—H5 | 120.1 | N4—C14—S1 | 114.4 (2) |
C4—C5—H5 | 120.1 | C13—C14—S1 | 122.53 (19) |
C5—C6—C1 | 118.9 (2) | N5—C15—O3 | 126.0 (2) |
C5—C6—H6 | 120.5 | N5—C15—S1 | 116.3 (2) |
C1—C6—H6 | 120.5 | O3—C15—S1 | 117.6 (2) |
N1—C7—O1 | 119.3 (3) | O3—C16—H16A | 109.5 |
N1—C7—C8 | 109.1 (2) | O3—C16—H16B | 109.5 |
O1—C7—C8 | 131.5 (2) | H16A—C16—H16B | 109.5 |
C7—C8—C9 | 103.0 (2) | O3—C16—H16C | 109.5 |
C7—C8—C12 | 130.8 (2) | H16A—C16—H16C | 109.5 |
C9—C8—C12 | 126.0 (3) | H16B—C16—H16C | 109.5 |
N2—C9—C8 | 111.9 (2) | ||
C7—N1—N2—C9 | 0.7 (3) | N1—C7—C8—C12 | 176.5 (2) |
C11—N1—N2—C9 | 179.4 (2) | O1—C7—C8—C12 | 0.4 (5) |
C13—O2—N3—C12 | 174.10 (19) | N1—N2—C9—C8 | −0.1 (3) |
C14—N4—N5—C15 | −1.2 (3) | N1—N2—C9—C10 | −179.3 (2) |
C6—C1—C2—C3 | 0.8 (4) | C7—C8—C9—N2 | −0.5 (3) |
Br1—C1—C2—C3 | −179.91 (19) | C12—C8—C9—N2 | −176.4 (2) |
C1—C2—C3—C4 | −0.4 (4) | C7—C8—C9—C10 | 178.7 (2) |
C2—C3—C4—C5 | −0.7 (4) | C12—C8—C9—C10 | 2.8 (4) |
C2—C3—C4—O1 | 179.6 (2) | O2—N3—C12—C8 | −179.9 (2) |
C7—O1—C4—C3 | −1.3 (4) | C7—C8—C12—N3 | 6.2 (4) |
C7—O1—C4—C5 | 179.0 (2) | C9—C8—C12—N3 | −179.1 (2) |
C3—C4—C5—C6 | 1.4 (4) | N3—O2—C13—C14 | 72.8 (3) |
O1—C4—C5—C6 | −178.9 (2) | N5—N4—C14—C13 | 178.9 (2) |
C4—C5—C6—C1 | −1.1 (4) | N5—N4—C14—S1 | 0.4 (3) |
C2—C1—C6—C5 | 0.0 (4) | O2—C13—C14—N4 | 118.3 (3) |
Br1—C1—C6—C5 | −179.35 (19) | O2—C13—C14—S1 | −63.3 (3) |
N2—N1—C7—O1 | 175.63 (19) | C15—S1—C14—N4 | 0.4 (2) |
C11—N1—C7—O1 | −3.0 (4) | C15—S1—C14—C13 | −178.2 (2) |
N2—N1—C7—C8 | −1.0 (3) | N4—N5—C15—O3 | 179.9 (2) |
C11—N1—C7—C8 | −179.6 (2) | N4—N5—C15—S1 | 1.5 (3) |
C4—O1—C7—N1 | 98.1 (3) | C16—O3—C15—N5 | 5.5 (4) |
C4—O1—C7—C8 | −86.2 (3) | C16—O3—C15—S1 | −176.12 (18) |
N1—C7—C8—C9 | 0.9 (3) | C14—S1—C15—N5 | −1.1 (2) |
O1—C7—C8—C9 | −175.2 (2) | C14—S1—C15—O3 | −179.7 (2) |
Cg is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11A···Cgi | 0.98 | 2.89 | 3.652 (4) | 125 |
Symmetry code: (i) −x+2, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C16H16BrN5O3S |
Mr | 438.31 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 113 |
a, b, c (Å) | 9.732 (3), 9.832 (2), 11.166 (3) |
α, β, γ (°) | 64.55 (2), 69.62 (2), 75.33 (3) |
V (Å3) | 897.5 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.43 |
Crystal size (mm) | 0.20 × 0.18 × 0.12 |
Data collection | |
Diffractometer | Rigaku Saturn724 CCD diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2008) |
Tmin, Tmax | 0.642, 0.759 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7729, 3175, 2363 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.054, 1.02 |
No. of reflections | 3175 |
No. of parameters | 238 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.36, −0.49 |
Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Cg is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11A···Cgi | 0.98 | 2.89 | 3.652 (4) | 125 |
Symmetry code: (i) −x+2, −y+2, −z+2. |
Acknowledgements
This work was supported by the Science and Technology Projects Fund of Nantong City (Nos. K2010016, AS2010005 and AS2011011), the Science Foundation of Nantong University (grant No. 11Z046) and the Science Foundation of Nantong University Xinglin College (grant No. 2010 K132).
References
Dai, H., Miao, W.-K., Wu, S.-S., Qin, X. & Fang, J.-X. (2011). Acta Cryst. E67, o775. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2008). CrystalClear. Rigaku Corporation, Toyko, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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In a continuation of our structural study of pyrazole oxime derivatives (Dai et al., 2011), we report here the crystal structure of the title compound, (I). In (I) (Fig. 1), all bonds lengths and angles are similar to those observed in the related compound (Dai et al., 2011). The dihedral angles between the substituted phenyl ring and the pyrazole ring and between the 1,3,4-thiadiazole ring and the pyrazole ring are 83.8 (3)° and 57.7 (2)°, respectively. The crystal packing displays short intermolecular C···C contacts of 3.203 (4) Å.