organic compounds
5-(4-Chlorophenoxy)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde O-[(2-chloropyridin-5-yl)methyl]oxime
aCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, People's Republic of China, and bState Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China
*Correspondence e-mail: nankaidx228@yahoo.com.cn
In the title molecule, C18H13Cl2F3N4O2, the intramolecular distance between the centroids of the benzene and pyridine rings is 3.953 (3) Å, and the trifluoromethyl group is rotationally disordered over two orientations in a 0.678 (19):0.322 (19) ratio. The crystal packing exhibits weak intermolecular C—H⋯F interactions.
Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku, 2008); cell CrystalClear (Rigaku, 2008); 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
https://doi.org/10.1107/S1600536811046459/cv5190sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046459/cv5190Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811046459/cv5190Isup3.cml
To a well stirred solution of 1-methyl-3-trifluoromethyl-5-(4-chlorophenoxy)- 1H-pyrazole-4-carbaldehyde oxime (3 mmol) and 2-chloro-5-chloromethylpyridine (3.6 mmol) in 40 ml of anhydrous DMF, was added powdered potassium carbonate (7.5 mmol). The resulting solution was heated to 363 K for 10 h and cooled to room temperature. The mixture was poured into water (180 ml) and extracted with dichloromethane (4 * 50 ml). The organic layer was washed with saturated brine (3 * 30 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the residue was separated by
on silica gel with petroleum ether/ethyl acetate (10:1 v/v) as and then recrystallized from ethyl acetate to give a colourless crystal.H atoms were placed in calculated positions, with C–H = 0.93 - 0.97 ° A, and refined as riding, with Uiso(H) = 1.2-1.5 Ueq(C). The trifluoromethyl was treated as disordered over two orientations. The displacement parameters of atoms F1, F2, F3, F1', F2' and F3' were restrained to behave approximately isotropic.
As a continuation of our structural study of pyrazole
(Dai et al., 2011), we report here the 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 planes of the pyridyl and pyrazole rings, and between the benzene and the pyrazole rings are 91.0 (3)° and 95.8 (3)°, respectively. The crystal packing displays weak intermolecular C—H···F interactions (Table 1).
For the
of a related pyrazole oxime studied recently by our group, see: Dai et al. (2011).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. |
C18H13Cl2F3N4O2 | F(000) = 904 |
Mr = 445.22 | Dx = 1.554 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4362 reflections |
a = 12.269 (3) Å | θ = 1.8–27.9° |
b = 10.443 (2) Å | µ = 0.39 mm−1 |
c = 15.702 (3) Å | T = 113 K |
β = 108.93 (3)° | Monoclinic, colourless |
V = 1902.9 (7) Å3 | 0.14 × 0.10 × 0.08 mm |
Z = 4 |
Rigaku Saturn diffractometer | 3356 independent reflections |
Radiation source: rotating anode | 2845 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.041 |
ω scans | θmax = 25.0°, θmin = 2.4° |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008) | h = −14→14 |
Tmin = 0.947, Tmax = 0.969 | k = −12→12 |
10759 measured reflections | l = −14→18 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0531P)2] where P = (Fo2 + 2Fc2)/3 |
3356 reflections | (Δ/σ)max = 0.003 |
291 parameters | Δρmax = 0.29 e Å−3 |
66 restraints | Δρmin = −0.26 e Å−3 |
C18H13Cl2F3N4O2 | V = 1902.9 (7) Å3 |
Mr = 445.22 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.269 (3) Å | µ = 0.39 mm−1 |
b = 10.443 (2) Å | T = 113 K |
c = 15.702 (3) Å | 0.14 × 0.10 × 0.08 mm |
β = 108.93 (3)° |
Rigaku Saturn diffractometer | 3356 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008) | 2845 reflections with I > 2σ(I) |
Tmin = 0.947, Tmax = 0.969 | Rint = 0.041 |
10759 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 66 restraints |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.29 e Å−3 |
3356 reflections | Δρmin = −0.26 e Å−3 |
291 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 | Occ. (<1) | |
Cl1 | 0.42312 (4) | 0.81673 (5) | 1.05301 (4) | 0.03177 (16) | |
Cl2 | 0.24719 (4) | 0.78497 (5) | 0.81487 (3) | 0.02958 (16) | |
F1 | 1.0291 (4) | 0.1147 (5) | 1.0472 (5) | 0.0485 (14) | 0.678 (19) |
F2 | 0.8486 (6) | 0.0969 (7) | 1.0153 (6) | 0.0436 (15) | 0.678 (19) |
F3 | 0.9173 (8) | 0.1880 (6) | 0.9233 (3) | 0.0509 (13) | 0.678 (19) |
F1' | 0.8773 (14) | 0.0850 (14) | 1.0406 (10) | 0.040 (3) | 0.322 (19) |
F2' | 0.8654 (15) | 0.1804 (12) | 0.9205 (6) | 0.052 (3) | 0.322 (19) |
F3' | 1.0278 (9) | 0.1329 (11) | 1.0091 (13) | 0.054 (3) | 0.322 (19) |
O1 | 0.89000 (10) | 0.62356 (11) | 1.10140 (8) | 0.0181 (3) | |
O2 | 0.76286 (11) | 0.60323 (12) | 0.81549 (8) | 0.0197 (3) | |
N1 | 0.97610 (13) | 0.30373 (14) | 1.14348 (10) | 0.0184 (3) | |
N2 | 0.96106 (13) | 0.42594 (15) | 1.16558 (10) | 0.0177 (3) | |
N3 | 0.80499 (12) | 0.57770 (15) | 0.90895 (9) | 0.0180 (3) | |
N4 | 0.43641 (14) | 0.66049 (15) | 0.83015 (11) | 0.0229 (4) | |
C1 | 0.92933 (16) | 0.17597 (18) | 1.00931 (12) | 0.0217 (4) | |
C2 | 0.92895 (15) | 0.30085 (17) | 1.05422 (12) | 0.0173 (4) | |
C3 | 0.88375 (15) | 0.41957 (17) | 1.01704 (12) | 0.0163 (4) | |
C4 | 0.90697 (14) | 0.49692 (17) | 1.09258 (11) | 0.0159 (4) | |
C5 | 1.00381 (17) | 0.4675 (2) | 1.25933 (11) | 0.0254 (5) | |
H5A | 0.9811 | 0.5546 | 1.2635 | 0.038* | |
H5B | 1.0863 | 0.4615 | 1.2812 | 0.038* | |
H5C | 0.9721 | 0.4137 | 1.2950 | 0.038* | |
C6 | 0.77559 (15) | 0.66348 (17) | 1.08527 (11) | 0.0171 (4) | |
C7 | 0.69070 (16) | 0.58030 (18) | 1.09125 (11) | 0.0189 (4) | |
H7 | 0.7065 | 0.4937 | 1.1029 | 0.023* | |
C8 | 0.58119 (17) | 0.62885 (18) | 1.07952 (12) | 0.0206 (4) | |
H8 | 0.5226 | 0.5744 | 1.0827 | 0.025* | |
C9 | 0.55957 (17) | 0.75740 (18) | 1.06322 (12) | 0.0204 (4) | |
C10 | 0.64499 (16) | 0.84005 (18) | 1.05618 (12) | 0.0220 (4) | |
H10 | 0.6293 | 0.9266 | 1.0444 | 0.026* | |
C11 | 0.75420 (17) | 0.79174 (17) | 1.06702 (12) | 0.0193 (4) | |
H11 | 0.8123 | 0.8455 | 1.0620 | 0.023* | |
C12 | 0.83287 (15) | 0.46034 (18) | 0.92371 (12) | 0.0177 (4) | |
H12 | 0.8212 | 0.4026 | 0.8765 | 0.021* | |
C13 | 0.72665 (16) | 0.73399 (18) | 0.80495 (12) | 0.0203 (4) | |
H13A | 0.7263 | 0.7643 | 0.7465 | 0.024* | |
H13B | 0.7817 | 0.7853 | 0.8505 | 0.024* | |
C14 | 0.60834 (16) | 0.75256 (17) | 0.81277 (11) | 0.0173 (4) | |
C15 | 0.55696 (17) | 0.87257 (19) | 0.80193 (13) | 0.0232 (4) | |
H15 | 0.5971 | 0.9441 | 0.7929 | 0.028* | |
C16 | 0.44578 (17) | 0.88534 (19) | 0.80457 (13) | 0.0250 (5) | |
H16 | 0.4099 | 0.9649 | 0.7984 | 0.030* | |
C17 | 0.39031 (16) | 0.77536 (19) | 0.81674 (12) | 0.0211 (4) | |
C18 | 0.54451 (16) | 0.65150 (18) | 0.82871 (12) | 0.0211 (4) | |
H18 | 0.5794 | 0.5714 | 0.8392 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0236 (3) | 0.0318 (3) | 0.0403 (3) | 0.0106 (2) | 0.0108 (2) | 0.0023 (2) |
Cl2 | 0.0196 (3) | 0.0357 (3) | 0.0373 (3) | 0.0061 (2) | 0.0147 (2) | 0.0090 (2) |
F1 | 0.0318 (16) | 0.0334 (17) | 0.065 (3) | 0.0189 (13) | −0.0060 (15) | −0.0266 (18) |
F2 | 0.038 (2) | 0.030 (2) | 0.076 (4) | −0.0155 (17) | 0.036 (2) | −0.021 (2) |
F3 | 0.108 (4) | 0.0256 (13) | 0.0330 (16) | 0.004 (3) | 0.042 (2) | −0.0057 (12) |
F1' | 0.076 (7) | 0.014 (3) | 0.043 (5) | −0.016 (4) | 0.037 (5) | −0.007 (3) |
F2' | 0.092 (7) | 0.026 (3) | 0.030 (3) | 0.013 (5) | 0.005 (4) | −0.008 (2) |
F3' | 0.029 (3) | 0.047 (4) | 0.103 (7) | −0.010 (3) | 0.044 (4) | −0.041 (5) |
O1 | 0.0169 (7) | 0.0131 (6) | 0.0238 (7) | −0.0001 (5) | 0.0061 (5) | −0.0023 (5) |
O2 | 0.0201 (7) | 0.0238 (7) | 0.0148 (6) | 0.0045 (6) | 0.0051 (5) | 0.0026 (5) |
N1 | 0.0178 (8) | 0.0160 (8) | 0.0231 (8) | 0.0020 (7) | 0.0087 (7) | 0.0020 (6) |
N2 | 0.0188 (8) | 0.0169 (8) | 0.0191 (8) | 0.0020 (7) | 0.0087 (7) | 0.0009 (6) |
N3 | 0.0167 (8) | 0.0237 (9) | 0.0135 (7) | 0.0028 (7) | 0.0049 (6) | 0.0032 (7) |
N4 | 0.0208 (9) | 0.0206 (9) | 0.0295 (9) | 0.0007 (7) | 0.0115 (7) | 0.0026 (7) |
C1 | 0.0201 (11) | 0.0190 (10) | 0.0277 (10) | −0.0003 (9) | 0.0100 (9) | 0.0008 (8) |
C2 | 0.0151 (9) | 0.0172 (10) | 0.0229 (9) | −0.0008 (8) | 0.0107 (8) | −0.0005 (8) |
C3 | 0.0144 (9) | 0.0161 (9) | 0.0204 (9) | 0.0002 (8) | 0.0083 (8) | 0.0001 (7) |
C4 | 0.0132 (9) | 0.0149 (9) | 0.0210 (9) | 0.0006 (7) | 0.0074 (8) | 0.0004 (7) |
C5 | 0.0309 (12) | 0.0278 (11) | 0.0167 (9) | −0.0003 (9) | 0.0065 (9) | 0.0000 (8) |
C6 | 0.0175 (10) | 0.0197 (10) | 0.0144 (9) | 0.0025 (8) | 0.0055 (8) | −0.0018 (7) |
C7 | 0.0238 (10) | 0.0138 (9) | 0.0204 (9) | 0.0007 (8) | 0.0090 (8) | −0.0010 (8) |
C8 | 0.0212 (10) | 0.0208 (10) | 0.0216 (9) | −0.0034 (8) | 0.0094 (8) | −0.0014 (8) |
C9 | 0.0198 (11) | 0.0232 (10) | 0.0179 (9) | 0.0048 (8) | 0.0058 (8) | −0.0020 (8) |
C10 | 0.0288 (11) | 0.0149 (9) | 0.0221 (9) | 0.0026 (8) | 0.0079 (9) | 0.0014 (8) |
C11 | 0.0239 (10) | 0.0151 (9) | 0.0200 (9) | −0.0030 (8) | 0.0086 (8) | −0.0012 (7) |
C12 | 0.0155 (9) | 0.0202 (10) | 0.0178 (9) | −0.0014 (8) | 0.0057 (8) | −0.0029 (8) |
C13 | 0.0200 (11) | 0.0200 (10) | 0.0211 (9) | 0.0015 (8) | 0.0069 (8) | 0.0051 (8) |
C14 | 0.0189 (10) | 0.0193 (10) | 0.0135 (8) | −0.0018 (8) | 0.0048 (8) | 0.0012 (7) |
C15 | 0.0242 (11) | 0.0198 (10) | 0.0277 (10) | −0.0022 (9) | 0.0114 (9) | 0.0028 (8) |
C16 | 0.0280 (11) | 0.0188 (10) | 0.0311 (11) | 0.0058 (9) | 0.0136 (9) | 0.0060 (8) |
C17 | 0.0169 (10) | 0.0275 (11) | 0.0199 (9) | 0.0022 (9) | 0.0075 (8) | 0.0023 (8) |
C18 | 0.0208 (10) | 0.0187 (10) | 0.0248 (10) | 0.0022 (8) | 0.0090 (8) | 0.0016 (8) |
Cl1—C9 | 1.743 (2) | C5—H5B | 0.9600 |
Cl2—C17 | 1.7496 (19) | C5—H5C | 0.9600 |
F1—C1 | 1.338 (4) | C6—C11 | 1.377 (3) |
F2—C1 | 1.316 (5) | C6—C7 | 1.383 (3) |
F3—C1 | 1.317 (4) | C7—C8 | 1.391 (3) |
F1'—C1 | 1.324 (9) | C7—H7 | 0.9300 |
F2'—C1 | 1.362 (8) | C8—C9 | 1.376 (3) |
F3'—C1 | 1.291 (7) | C8—H8 | 0.9300 |
O1—C4 | 1.353 (2) | C9—C10 | 1.389 (3) |
O1—C6 | 1.406 (2) | C10—C11 | 1.390 (3) |
O2—N3 | 1.4141 (18) | C10—H10 | 0.9300 |
O2—C13 | 1.429 (2) | C11—H11 | 0.9300 |
N1—C2 | 1.332 (2) | C12—H12 | 0.9300 |
N1—N2 | 1.351 (2) | C13—C14 | 1.509 (2) |
N2—C4 | 1.345 (2) | C13—H13A | 0.9700 |
N2—C5 | 1.459 (2) | C13—H13B | 0.9700 |
N3—C12 | 1.273 (2) | C14—C18 | 1.384 (3) |
N4—C17 | 1.314 (2) | C14—C15 | 1.388 (3) |
N4—C18 | 1.337 (2) | C15—C16 | 1.384 (3) |
C1—C2 | 1.483 (3) | C15—H15 | 0.9300 |
C2—C3 | 1.405 (3) | C16—C17 | 1.380 (3) |
C3—C4 | 1.386 (2) | C16—H16 | 0.9300 |
C3—C12 | 1.458 (2) | C18—H18 | 0.9300 |
C5—H5A | 0.9600 | ||
C4—O1—C6 | 116.69 (14) | H5B—C5—H5C | 109.5 |
N3—O2—C13 | 107.19 (13) | C11—C6—C7 | 121.89 (17) |
C2—N1—N2 | 104.05 (14) | C11—C6—O1 | 115.95 (16) |
C4—N2—N1 | 111.86 (14) | C7—C6—O1 | 122.10 (16) |
C4—N2—C5 | 127.74 (16) | C6—C7—C8 | 118.58 (17) |
N1—N2—C5 | 120.38 (15) | C6—C7—H7 | 120.7 |
C12—N3—O2 | 110.88 (14) | C8—C7—H7 | 120.7 |
C17—N4—C18 | 116.05 (16) | C9—C8—C7 | 119.98 (18) |
F3'—C1—F2 | 120.6 (6) | C9—C8—H8 | 120.0 |
F3'—C1—F3 | 79.8 (6) | C7—C8—H8 | 120.0 |
F2—C1—F3 | 107.2 (4) | C8—C9—C10 | 121.05 (18) |
F3'—C1—F1' | 108.4 (9) | C8—C9—Cl1 | 119.03 (15) |
F2—C1—F1' | 19.8 (7) | C10—C9—Cl1 | 119.91 (15) |
F3—C1—F1' | 122.8 (7) | C9—C10—C11 | 119.14 (18) |
F3'—C1—F1 | 27.4 (6) | C9—C10—H10 | 120.4 |
F2—C1—F1 | 105.6 (4) | C11—C10—H10 | 120.4 |
F3—C1—F1 | 106.5 (3) | C6—C11—C10 | 119.32 (17) |
F1'—C1—F1 | 88.5 (7) | C6—C11—H11 | 120.3 |
F3'—C1—F2' | 103.7 (5) | C10—C11—H11 | 120.3 |
F2—C1—F2' | 84.1 (6) | N3—C12—C3 | 117.79 (16) |
F3—C1—F2' | 27.1 (6) | N3—C12—H12 | 121.1 |
F1'—C1—F2' | 102.5 (8) | C3—C12—H12 | 121.1 |
F1—C1—F2' | 127.7 (6) | O2—C13—C14 | 112.62 (15) |
F3'—C1—C2 | 117.1 (5) | O2—C13—H13A | 109.1 |
F2—C1—C2 | 113.5 (4) | C14—C13—H13A | 109.1 |
F3—C1—C2 | 112.8 (3) | O2—C13—H13B | 109.1 |
F1'—C1—C2 | 112.2 (8) | C14—C13—H13B | 109.1 |
F1—C1—C2 | 110.6 (2) | H13A—C13—H13B | 107.8 |
F2'—C1—C2 | 111.6 (5) | C18—C14—C15 | 116.70 (17) |
N1—C2—C3 | 113.29 (16) | C18—C14—C13 | 122.17 (17) |
N1—C2—C1 | 116.93 (16) | C15—C14—C13 | 121.11 (17) |
C3—C2—C1 | 129.77 (17) | C16—C15—C14 | 119.73 (18) |
C4—C3—C2 | 102.40 (15) | C16—C15—H15 | 120.1 |
C4—C3—C12 | 126.31 (17) | C14—C15—H15 | 120.1 |
C2—C3—C12 | 131.13 (16) | C17—C16—C15 | 117.33 (18) |
N2—C4—O1 | 120.07 (15) | C17—C16—H16 | 121.3 |
N2—C4—C3 | 108.40 (15) | C15—C16—H16 | 121.3 |
O1—C4—C3 | 131.42 (16) | N4—C17—C16 | 125.19 (17) |
N2—C5—H5A | 109.5 | N4—C17—Cl2 | 115.64 (14) |
N2—C5—H5B | 109.5 | C16—C17—Cl2 | 119.18 (15) |
H5A—C5—H5B | 109.5 | N4—C18—C14 | 124.88 (18) |
N2—C5—H5C | 109.5 | N4—C18—H18 | 117.6 |
H5A—C5—H5C | 109.5 | C14—C18—H18 | 117.6 |
C2—N1—N2—C4 | −0.33 (19) | C12—C3—C4—O1 | 0.4 (3) |
C2—N1—N2—C5 | −179.09 (15) | C4—O1—C6—C11 | −160.71 (15) |
C13—O2—N3—C12 | 176.22 (14) | C4—O1—C6—C7 | 22.0 (2) |
N2—N1—C2—C3 | 0.4 (2) | C11—C6—C7—C8 | −0.8 (3) |
N2—N1—C2—C1 | −178.44 (14) | O1—C6—C7—C8 | 176.26 (15) |
F3'—C1—C2—N1 | −69.1 (10) | C6—C7—C8—C9 | −0.6 (3) |
F2—C1—C2—N1 | 78.6 (5) | C7—C8—C9—C10 | 1.5 (3) |
F3—C1—C2—N1 | −159.1 (5) | C7—C8—C9—Cl1 | −177.60 (14) |
F1'—C1—C2—N1 | 57.1 (8) | C8—C9—C10—C11 | −0.9 (3) |
F1—C1—C2—N1 | −40.0 (5) | Cl1—C9—C10—C11 | 178.20 (13) |
F2'—C1—C2—N1 | 171.6 (10) | C7—C6—C11—C10 | 1.4 (3) |
F3'—C1—C2—C3 | 112.2 (10) | O1—C6—C11—C10 | −175.83 (15) |
F2—C1—C2—C3 | −100.0 (5) | C9—C10—C11—C6 | −0.6 (3) |
F3—C1—C2—C3 | 22.2 (5) | O2—N3—C12—C3 | 176.84 (14) |
F1'—C1—C2—C3 | −121.5 (8) | C4—C3—C12—N3 | −1.1 (3) |
F1—C1—C2—C3 | 141.4 (5) | C2—C3—C12—N3 | −175.70 (18) |
F2'—C1—C2—C3 | −7.1 (10) | N3—O2—C13—C14 | −81.09 (17) |
N1—C2—C3—C4 | −0.4 (2) | O2—C13—C14—C18 | 0.2 (2) |
C1—C2—C3—C4 | 178.33 (17) | O2—C13—C14—C15 | −178.18 (16) |
N1—C2—C3—C12 | 175.19 (17) | C18—C14—C15—C16 | −2.0 (3) |
C1—C2—C3—C12 | −6.1 (3) | C13—C14—C15—C16 | 176.44 (17) |
N1—N2—C4—O1 | −176.49 (14) | C14—C15—C16—C17 | −1.0 (3) |
C5—N2—C4—O1 | 2.2 (3) | C18—N4—C17—C16 | −2.2 (3) |
N1—N2—C4—C3 | 0.12 (19) | C18—N4—C17—Cl2 | 177.86 (13) |
C5—N2—C4—C3 | 178.76 (16) | C15—C16—C17—N4 | 3.3 (3) |
C6—O1—C4—N2 | −111.17 (17) | C15—C16—C17—Cl2 | −176.79 (14) |
C6—O1—C4—C3 | 73.1 (2) | C17—N4—C18—C14 | −1.2 (3) |
C2—C3—C4—N2 | 0.13 (18) | C15—C14—C18—N4 | 3.3 (3) |
C12—C3—C4—N2 | −175.71 (16) | C13—C14—C18—N4 | −175.16 (17) |
C2—C3—C4—O1 | 176.22 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5C···F3i | 0.96 | 2.55 | 3.488 (7) | 165 |
C11—H11···F3′ii | 0.93 | 2.56 | 3.358 (14) | 144 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C18H13Cl2F3N4O2 |
Mr | 445.22 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 113 |
a, b, c (Å) | 12.269 (3), 10.443 (2), 15.702 (3) |
β (°) | 108.93 (3) |
V (Å3) | 1902.9 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.39 |
Crystal size (mm) | 0.14 × 0.10 × 0.08 |
Data collection | |
Diffractometer | Rigaku Saturn |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2008) |
Tmin, Tmax | 0.947, 0.969 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10759, 3356, 2845 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.090, 1.07 |
No. of reflections | 3356 |
No. of parameters | 291 |
No. of restraints | 66 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.26 |
Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5C···F3i | 0.96 | 2.55 | 3.488 (7) | 165 |
C11—H11···F3'ii | 0.93 | 2.56 | 3.358 (14) | 144 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, −y+1, −z+2. |
Acknowledgements
This work was supported by the National Natural Science Foundation of China (NNSFC) (grant No. 20772068), the Science and Technology Projects Fund of Nantong City (grant No. K2010016, AS2010005), the Science Foundation of Nantong University (grant No. 09Z010, 09C001) and the Scientific Research Foundation for Talent Introduction of Nantong University.
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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As a continuation of our structural study of pyrazole oximes (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 planes of the pyridyl and pyrazole rings, and between the benzene and the pyrazole rings are 91.0 (3)° and 95.8 (3)°, respectively. The crystal packing displays weak intermolecular C—H···F interactions (Table 1).