1-Methyl-3-trifluoro-methyl-5-[(3-chloro-phen-yl)sulfanyl]-1H-pyrazole-4-carbaldehyde O-(4-chloro-benzo-yl)oxime.

In the title compound, C(19)H(12)Cl(2)F(3)N(3)O(2)S, the 3-chloro-phenyl and 4-chloro-phenyl rings form dihedral angles 89.5 (2) and 11.4 (2)°, respectively, with the pyrazole ring. In the crystal, mol-ecules 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 = 474.28

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.137

S = 1.10

3654 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.38 e Å−3

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.

Crystal structure: contains datablock(s) r80421a, I. DOI: 10.1107/S1600536811047970/cv5193sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047970/cv5193Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047970/cv5193Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H12Cl2F3N3O2S	F(000) = 960
Mr = 474.28	Dx = 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

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

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(Fo2) + (0.0717P)2 + 0.2323P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
3654 reflections	Δρmax = 0.39 e Å−3
273 parameters	Δρmin = −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)

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
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*

	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)

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)

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

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) .