1-Methyl-3-trifluoro­methyl-5-[(3-chloro­phen­yl)sulfanyl]-1H-pyrazole-4-carbaldehyde O-(4-chloro­benzo­yl)oxime

Dai, H.; Zhang, H.-J.; Shi, L.; Luo, K.-P.; Shi, Y.-J.

doi:10.1107/S1600536811047970

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3343

https://doi.org/10.1107/S1600536811047970

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1-Methyl-3-trifluoromethyl-5-[(3-chlorophenyl)sulfanyl]-1H-pyrazole-4-carbaldehyde O-(4-chlorobenzoyl)oxime

Hong Dai,^a Hai-Jun Zhang,^a Lei Shi,^a Kun-Peng Luo ^a and Yu-Jun Shi ^a ^*

^aCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, People's Republic of China
^*Correspondence e-mail: nankaidx228@yahoo.com.cn

(Received 4 November 2011; accepted 11 November 2011; online 19 November 2011)

In the title compound, C₁₉H₁₂Cl₂F₃N₃O₂S, the 3-chlorophenyl and 4-chlorophenyl rings form dihedral angles 89.5 (2) and 11.4 (2)°, respectively, with the pyrazole ring. In the crystal, molecules related by translation along the a axis are linked into chains via C—H⋯N hydrogen bonds.

Related literature

For the crystal structure of a related pyrazole oxime studied recently by our group, see: Dai et al. (2011 ).

Experimental

Crystal data

C₁₉H₁₂Cl₂F₃N₃O₂S
M_r = 474.28
Monoclinic, P 2₁ /n
a = 8.1405 (16) Å
b = 18.680 (4) Å
c = 13.737 (3) Å
β = 96.10 (3)°
V = 2077.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 113 K
0.18 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn CCD area detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ) T_min = 0.922, T_max = 0.947
11802 measured reflections
3654 independent reflections
2794 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.137
S = 1.10
3654 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N2ⁱ	0.93	2.49	3.365 (4)	156
Symmetry code: (i) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2008); cell refinement: 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

Crystal structure: contains datablocks r80421a, I. DOI: https://doi.org/10.1107/S1600536811047970/cv5193sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047970/cv5193Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811047970/cv5193Isup3.cml

checkCIF report

Comment top

As a continuation of our structural investigation of pyrazole oxime esters (Dai et al., 2011), we report here the structure of the title compound (I).

In (I) (Fig. 1), all bonds lengths and angles are comparable with those observed in the related compound (Dai et al., 2011). The mean planes p1 (C7/C8/C9/N2/N1), p2 (C1/C2/C3/C4/C5/C6) and p3 (C13/C14/C15/C16/C17/C18) form the following dihedral angles - p2/p1 89.5 (2)°, p3/p1 11.4 (3)°. The crystal packing shows weak intermolecular C—H···N interactions (Table 1), which link molecules into chains along the a axis.

Related literature top

For the crystal structure of a related pyrazole oxime studied recently by our group, see: Dai et al. (2011).

Experimental top

To a well stirred solution of 1-methyl-3-trifluoromethyl-5-(3-chlorophenthio)- 1H-pyrazole-4-carbaldehyde oxime (4 mmol), and pyridine (5 ml) in 40 ml of dichloromethane, was added dropwise 4-chlorobenzoyl chloride (5 mmol) at room temperature. The resulting solution was heated to reflux for 7 h and cooled to room temperature. The mixture 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 column chromatography on silica gel with petroleum ether/ethyl acetate (12:1 v/v) as eluent, and then recrystallized from petroleum ether/ethyl acetate acetate to give a colourless crystal.

Structure description top

As a continuation of our structural investigation of pyrazole oxime esters (Dai et al., 2011), we report here the structure of the title compound (I).

For the crystal structure of a related pyrazole oxime studied recently by our group, see: Dai et al. (2011).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: 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).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering and 30% probabilty displacement ellipsoids.

1-Methyl-3-trifluoromethyl-5-[(3-chlorophenyl)sulfanyl]-1H-pyrazole-4- carbaldehyde O-(4-chlorobenzoyl)oxime top

Crystal data top

C₁₉H₁₂Cl₂F₃N₃O₂S	F(000) = 960
M_r = 474.28	D_x = 1.517 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4368 reflections
a = 8.1405 (16) Å	θ = 2.2–27.9°
b = 18.680 (4) Å	µ = 0.46 mm⁻¹
c = 13.737 (3) Å	T = 113 K
β = 96.10 (3)°	Monoclinic, colourless
V = 2077.0 (7) Å³	0.18 × 0.16 × 0.12 mm
Z = 4

Data collection top

Rigaku Saturn CCD area detector diffractometer	3654 independent reflections
Radiation source: rotating anode	2794 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.039
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.2°
ω and φ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −22→22
T_min = 0.922, T_max = 0.947	l = −14→16
11802 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.0717P)² + 0.2323P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
3654 reflections	Δρ_max = 0.39 e Å⁻³
273 parameters	Δρ_min = −0.38 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (3)

Crystal data top

C₁₉H₁₂Cl₂F₃N₃O₂S	V = 2077.0 (7) Å³
M_r = 474.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.1405 (16) Å	µ = 0.46 mm⁻¹
b = 18.680 (4) Å	T = 113 K
c = 13.737 (3) Å	0.18 × 0.16 × 0.12 mm
β = 96.10 (3)°

Data collection top

Rigaku Saturn CCD area detector diffractometer	3654 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	2794 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.947	R_int = 0.039
11802 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.10	Δρ_max = 0.39 e Å⁻³
3654 reflections	Δρ_min = −0.38 e Å⁻³
273 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

	x	y	z	U_iso*/U_eq
Cl1	1.09484 (13)	0.84104 (6)	0.56388 (10)	0.1131 (4)
Cl2	1.29709 (11)	0.74602 (6)	1.34884 (7)	0.0961 (4)
S1	0.64859 (10)	1.00969 (4)	0.71200 (6)	0.0663 (3)
F1	0.1729 (2)	0.85215 (8)	0.92153 (14)	0.0775 (5)
F2	−0.0064 (2)	0.93357 (11)	0.88380 (14)	0.0867 (6)
F3	0.1826 (2)	0.94978 (10)	1.00144 (12)	0.0778 (5)
O1	0.6832 (2)	0.87708 (10)	1.04766 (12)	0.0532 (5)
O2	0.5304 (3)	0.84250 (12)	1.16752 (17)	0.0833 (7)
N1	0.3126 (3)	1.00802 (11)	0.71276 (16)	0.0566 (6)
N2	0.1875 (3)	0.98695 (11)	0.76284 (16)	0.0543 (6)
N3	0.5309 (3)	0.89838 (12)	0.99338 (15)	0.0538 (6)
C1	0.5668 (4)	0.88041 (15)	0.6144 (2)	0.0607 (7)
H1	0.4569	0.8886	0.6238	0.073*
C2	0.6110 (4)	0.81988 (17)	0.5655 (2)	0.0688 (8)
H2	0.5297	0.7873	0.5423	0.083*
C3	0.7709 (4)	0.80690 (17)	0.5504 (2)	0.0715 (8)
H3	0.7993	0.7657	0.5180	0.086*
C4	0.8894 (4)	0.85576 (16)	0.5841 (2)	0.0654 (8)
C5	0.8510 (3)	0.91618 (15)	0.63472 (18)	0.0584 (7)
H5	0.9336	0.9479	0.6587	0.070*
C6	0.6885 (3)	0.92892 (14)	0.64942 (16)	0.0508 (6)
C7	0.4631 (3)	0.98935 (13)	0.75808 (18)	0.0492 (6)
C8	0.4342 (3)	0.95423 (12)	0.84390 (16)	0.0434 (6)
C9	0.2602 (3)	0.95408 (12)	0.84192 (16)	0.0433 (6)
C10	0.1528 (3)	0.92283 (13)	0.91187 (19)	0.0518 (6)
C11	0.5643 (3)	0.92724 (12)	0.91488 (18)	0.0468 (6)
H11	0.6739	0.9313	0.9023	0.056*
C12	0.6607 (3)	0.84774 (13)	1.13649 (19)	0.0513 (6)
C13	0.8222 (3)	0.82499 (13)	1.18756 (18)	0.0473 (6)
C14	0.8200 (4)	0.77728 (14)	1.2655 (2)	0.0584 (7)
H14	0.7197	0.7611	1.2838	0.070*
C15	0.9663 (4)	0.75393 (14)	1.3154 (2)	0.0629 (8)
H15	0.9651	0.7220	1.3673	0.076*
C16	1.1137 (3)	0.77827 (15)	1.2879 (2)	0.0582 (7)
C17	1.1198 (3)	0.82612 (14)	1.2119 (2)	0.0555 (7)
H17	1.2206	0.8425	1.1946	0.067*
C18	0.9727 (3)	0.84924 (13)	1.16177 (19)	0.0517 (6)
H18	0.9749	0.8814	1.1102	0.062*
C19	0.2742 (5)	1.0461 (2)	0.6195 (2)	0.0884 (11)
H19A	0.2762	1.0130	0.5662	0.133*
H19B	0.3549	1.0830	0.6139	0.133*
H19C	0.1665	1.0673	0.6176	0.133*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0650 (6)	0.1302 (9)	0.1451 (10)	0.0138 (5)	0.0163 (6)	−0.0332 (7)
Cl2	0.0651 (6)	0.1262 (8)	0.0921 (6)	0.0249 (5)	−0.0154 (5)	0.0214 (5)
S1	0.0663 (5)	0.0631 (5)	0.0734 (5)	−0.0207 (3)	0.0257 (4)	−0.0077 (3)
F1	0.0803 (13)	0.0574 (10)	0.0992 (13)	−0.0039 (8)	0.0302 (10)	0.0083 (8)
F2	0.0379 (9)	0.1262 (16)	0.0967 (13)	0.0030 (9)	0.0103 (9)	0.0184 (11)
F3	0.0809 (13)	0.0988 (13)	0.0579 (10)	−0.0146 (10)	0.0263 (9)	−0.0142 (9)
O1	0.0370 (10)	0.0717 (11)	0.0500 (9)	0.0044 (8)	0.0002 (8)	0.0088 (8)
O2	0.0458 (13)	0.1175 (18)	0.0892 (15)	0.0122 (11)	0.0195 (12)	0.0396 (13)
N1	0.0603 (15)	0.0591 (13)	0.0498 (12)	0.0021 (11)	0.0025 (11)	0.0099 (10)
N2	0.0485 (13)	0.0582 (12)	0.0553 (13)	0.0069 (10)	0.0016 (11)	0.0036 (10)
N3	0.0374 (12)	0.0684 (14)	0.0536 (12)	0.0051 (10)	−0.0040 (10)	0.0042 (10)
C1	0.0530 (17)	0.0707 (17)	0.0595 (16)	−0.0153 (13)	0.0109 (13)	−0.0025 (13)
C2	0.072 (2)	0.0704 (18)	0.0629 (17)	−0.0216 (16)	0.0033 (16)	−0.0037 (14)
C3	0.080 (2)	0.0724 (19)	0.0627 (18)	−0.0051 (17)	0.0113 (16)	−0.0053 (15)
C4	0.0582 (19)	0.079 (2)	0.0587 (16)	0.0060 (15)	0.0049 (14)	0.0002 (14)
C5	0.0490 (17)	0.0761 (18)	0.0486 (14)	−0.0088 (13)	−0.0013 (12)	0.0014 (13)
C6	0.0522 (16)	0.0591 (15)	0.0413 (13)	−0.0098 (12)	0.0052 (12)	0.0070 (11)
C7	0.0483 (16)	0.0499 (13)	0.0498 (14)	−0.0037 (11)	0.0070 (12)	0.0012 (11)
C8	0.0411 (14)	0.0457 (12)	0.0432 (12)	−0.0016 (10)	0.0038 (10)	−0.0044 (10)
C9	0.0401 (14)	0.0469 (12)	0.0424 (12)	0.0035 (10)	0.0017 (10)	−0.0022 (10)
C10	0.0383 (15)	0.0564 (15)	0.0611 (16)	0.0019 (11)	0.0067 (12)	−0.0012 (12)
C11	0.0360 (13)	0.0532 (14)	0.0509 (14)	−0.0006 (10)	0.0026 (11)	−0.0028 (11)
C12	0.0453 (16)	0.0537 (14)	0.0549 (15)	−0.0002 (11)	0.0050 (13)	0.0065 (11)
C13	0.0425 (15)	0.0488 (13)	0.0505 (13)	0.0023 (11)	0.0048 (11)	0.0007 (11)
C14	0.0511 (16)	0.0626 (16)	0.0623 (16)	0.0010 (13)	0.0105 (13)	0.0150 (13)
C15	0.062 (2)	0.0667 (17)	0.0598 (17)	0.0091 (14)	0.0049 (14)	0.0170 (13)
C16	0.0517 (17)	0.0651 (16)	0.0554 (15)	0.0111 (13)	−0.0057 (13)	0.0009 (13)
C17	0.0418 (15)	0.0617 (16)	0.0627 (16)	−0.0018 (12)	0.0036 (13)	−0.0007 (13)
C18	0.0469 (16)	0.0531 (14)	0.0547 (14)	−0.0015 (11)	0.0032 (12)	0.0072 (11)
C19	0.103 (3)	0.096 (2)	0.0642 (19)	0.011 (2)	0.0001 (18)	0.0349 (18)

Geometric parameters (Å, º) top

Cl1—C4	1.746 (3)	C4—C5	1.379 (4)
Cl2—C16	1.740 (3)	C5—C6	1.380 (4)
S1—C7	1.740 (3)	C5—H5	0.9300
S1—C6	1.783 (3)	C7—C8	1.391 (3)
F1—C10	1.335 (3)	C8—C9	1.414 (3)
F2—C10	1.327 (3)	C8—C11	1.451 (3)
F3—C10	1.328 (3)	C9—C10	1.486 (4)
O1—C12	1.368 (3)	C11—H11	0.9300
O1—N3	1.434 (2)	C12—C13	1.485 (3)
O2—C12	1.189 (3)	C13—C18	1.387 (4)
N1—N2	1.347 (3)	C13—C14	1.394 (4)
N1—C7	1.359 (3)	C14—C15	1.381 (4)
N1—C19	1.469 (3)	C14—H14	0.9300
N2—C9	1.331 (3)	C15—C16	1.373 (4)
N3—C11	1.261 (3)	C15—H15	0.9300
C1—C2	1.382 (4)	C16—C17	1.380 (4)
C1—C6	1.390 (4)	C17—C18	1.385 (4)
C1—H1	0.9300	C17—H17	0.9300
C2—C3	1.361 (4)	C18—H18	0.9300
C2—H2	0.9300	C19—H19A	0.9600
C3—C4	1.372 (4)	C19—H19B	0.9600
C3—H3	0.9300	C19—H19C	0.9600

C7—S1—C6	101.54 (12)	F2—C10—F1	106.5 (2)
C12—O1—N3	112.63 (19)	F3—C10—F1	105.9 (2)
N2—N1—C7	112.6 (2)	F2—C10—C9	112.1 (2)
N2—N1—C19	119.0 (3)	F3—C10—C9	112.8 (2)
C7—N1—C19	128.4 (3)	F1—C10—C9	112.2 (2)
C9—N2—N1	104.9 (2)	N3—C11—C8	121.0 (2)
C11—N3—O1	108.1 (2)	N3—C11—H11	119.5
C2—C1—C6	119.3 (3)	C8—C11—H11	119.5
C2—C1—H1	120.4	O2—C12—O1	124.2 (2)
C6—C1—H1	120.4	O2—C12—C13	125.9 (2)
C3—C2—C1	121.5 (3)	O1—C12—C13	109.9 (2)
C3—C2—H2	119.3	C18—C13—C14	119.2 (2)
C1—C2—H2	119.3	C18—C13—C12	123.2 (2)
C2—C3—C4	118.7 (3)	C14—C13—C12	117.6 (2)
C2—C3—H3	120.7	C15—C14—C13	120.2 (3)
C4—C3—H3	120.7	C15—C14—H14	119.9
C3—C4—C5	121.7 (3)	C13—C14—H14	119.9
C3—C4—Cl1	119.5 (3)	C16—C15—C14	119.4 (3)
C5—C4—Cl1	118.8 (2)	C16—C15—H15	120.3
C4—C5—C6	119.1 (3)	C14—C15—H15	120.3
C4—C5—H5	120.4	C15—C16—C17	121.7 (2)
C6—C5—H5	120.4	C15—C16—Cl2	118.9 (2)
C5—C6—C1	119.7 (3)	C17—C16—Cl2	119.4 (2)
C5—C6—S1	116.3 (2)	C16—C17—C18	118.6 (3)
C1—C6—S1	124.0 (2)	C16—C17—H17	120.7
N1—C7—C8	106.5 (2)	C18—C17—H17	120.7
N1—C7—S1	123.51 (19)	C17—C18—C13	120.8 (2)
C8—C7—S1	130.0 (2)	C17—C18—H18	119.6
C7—C8—C9	104.1 (2)	C13—C18—H18	119.6
C7—C8—C11	123.8 (2)	N1—C19—H19A	109.5
C9—C8—C11	132.1 (2)	N1—C19—H19B	109.5
N2—C9—C8	111.9 (2)	H19A—C19—H19B	109.5
N2—C9—C10	117.9 (2)	N1—C19—H19C	109.5
C8—C9—C10	130.2 (2)	H19A—C19—H19C	109.5
F2—C10—F3	106.8 (2)	H19B—C19—H19C	109.5

C7—N1—N2—C9	0.0 (3)	C11—C8—C9—N2	178.2 (2)
C19—N1—N2—C9	179.5 (2)	C7—C8—C9—C10	178.2 (2)
C12—O1—N3—C11	177.4 (2)	C11—C8—C9—C10	−2.8 (4)
C6—C1—C2—C3	−0.3 (4)	N2—C9—C10—F2	−0.6 (3)
C1—C2—C3—C4	−0.7 (5)	C8—C9—C10—F2	−179.5 (2)
C2—C3—C4—C5	1.8 (5)	N2—C9—C10—F3	−121.2 (2)
C2—C3—C4—Cl1	−179.0 (2)	C8—C9—C10—F3	59.9 (3)
C3—C4—C5—C6	−2.0 (4)	N2—C9—C10—F1	119.2 (2)
Cl1—C4—C5—C6	178.8 (2)	C8—C9—C10—F1	−59.7 (3)
C4—C5—C6—C1	0.9 (4)	O1—N3—C11—C8	179.75 (19)
C4—C5—C6—S1	−178.0 (2)	C7—C8—C11—N3	177.1 (2)
C2—C1—C6—C5	0.2 (4)	C9—C8—C11—N3	−1.7 (4)
C2—C1—C6—S1	179.0 (2)	N3—O1—C12—O2	−2.5 (4)
C7—S1—C6—C5	−157.1 (2)	N3—O1—C12—C13	178.37 (19)
C7—S1—C6—C1	24.0 (2)	O2—C12—C13—C18	−161.7 (3)
N2—N1—C7—C8	−0.5 (3)	O1—C12—C13—C18	17.4 (3)
C19—N1—C7—C8	−179.9 (3)	O2—C12—C13—C14	17.8 (4)
N2—N1—C7—S1	−179.46 (17)	O1—C12—C13—C14	−163.0 (2)
C19—N1—C7—S1	1.1 (4)	C18—C13—C14—C15	−0.8 (4)
C6—S1—C7—N1	−96.1 (2)	C12—C13—C14—C15	179.7 (3)
C6—S1—C7—C8	85.2 (2)	C13—C14—C15—C16	0.2 (4)
N1—C7—C8—C9	0.7 (2)	C14—C15—C16—C17	0.5 (4)
S1—C7—C8—C9	179.61 (19)	C14—C15—C16—Cl2	−177.8 (2)
N1—C7—C8—C11	−178.3 (2)	C15—C16—C17—C18	−0.7 (4)
S1—C7—C8—C11	0.6 (4)	Cl2—C16—C17—C18	177.6 (2)
N1—N2—C9—C8	0.5 (3)	C16—C17—C18—C13	0.2 (4)
N1—N2—C9—C10	−178.6 (2)	C14—C13—C18—C17	0.6 (4)
C7—C8—C9—N2	−0.8 (3)	C12—C13—C18—C17	−179.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2ⁱ	0.93	2.49	3.365 (4)	156

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₂Cl₂F₃N₃O₂S
M_r	474.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	8.1405 (16), 18.680 (4), 13.737 (3)
β (°)	96.10 (3)
V (Å³)	2077.0 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.18 × 0.16 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD area detector
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2008)
T_min, T_max	0.922, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	11802, 3654, 2794
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.137, 1.10
No. of reflections	3654
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.38

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2ⁱ	0.93	2.49	3.365 (4)	156

Symmetry code: (i) x+1, y, z.

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 Nos. K2010016 and AS2010005), the Science Foundation of Nantong University (grant Nos. 09Z010 and 09C001) and the Scientific Research Foundation for Talent Introduction of Nantong University.

References

Dai, H., Shen, Y.-F., Chen, J., Chen, H.-L. & Shen, Y.-J. (2011). Acta Cryst. E67, o726. 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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Volume 67| Part 12| December 2011| Page o3343

https://doi.org/10.1107/S1600536811047970

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

1-Methyl-3-tri­fluoro­methyl-5-[(3-chloro­phen­yl)sulfanyl]-1H-pyrazole-4-carbaldehyde O-(4-chloro­benzo­yl)oxime

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Experimental

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Refinement

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References

organic compounds

1-Methyl-3-trifluoromethyl-5-[(3-chlorophenyl)sulfanyl]-1H-pyrazole-4-carbaldehyde O-(4-chlorobenzoyl)oxime