(E)-3-Methyl-5-(4-methyl-phen-oxy)-1-phenyl-1H-pyrazole-4-carbaldehyde O-[(2-chloro-1,3-thia-zol-5-yl)meth-yl]oxime.

In the title compound, C(22)H(19)ClN(4)O(2)S, the planes of the benzene ring, the substituted phenyl ring and the thia-zole ring make dihedral angles of 18.4 (3), 88.9 (2) and 63.0 (3)°, respectively, with the pyrazole ring.

Related literature

For the biological activity of pyrazole oxime ether derivatives, see: Drabek (1992 ▶); Motoba et al. (2000 ▶); Park et al. (2005 ▶); Watanabe et al. (2001 ▶). For the bioactivity of compounds containing a thia­zole ring, see: Araki (2004 ▶); Fahmy & Bekhit (2002 ▶); Manabe et al. (2003 ▶); Zhang et al. (2000 ▶).

Experimental

Crystal data

C22H19ClN4O2S

M = 438.92

Triclinic,

a = 8.114 (3) Å

b = 11.452 (4) Å

c = 12.494 (4) Å

α = 102.700 (6)°

β = 107.885 (6)°

γ = 93.634 (7)°

V = 1067.1 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 294 K

0.20 × 0.18 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.938, T max = 0.968

5562 measured reflections

3755 independent reflections

2030 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.124

S = 1.00

3755 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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 datablocks global, I. DOI: 10.1107/S1600536811006702/ds2094sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006702/ds2094Isup2.hkl

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

C22H19ClN4O2S	Z = 2
Mr = 438.92	F(000) = 456
Triclinic, P1	Dx = 1.366 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.114 (3) Å	Cell parameters from 1218 reflections
b = 11.452 (4) Å	θ = 2.7–22.3°
c = 12.494 (4) Å	µ = 0.30 mm−1
α = 102.700 (6)°	T = 294 K
β = 107.885 (6)°	Triclinic, colourless
γ = 93.634 (7)°	0.20 × 0.18 × 0.10 mm
V = 1067.1 (6) Å3

Bruker SMART CCD area-detector diffractometer	3755 independent reflections
Radiation source: fine-focus sealed tube	2030 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.938, Tmax = 0.968	k = −10→13
5562 measured reflections	l = −14→14

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.049P)2 + 0.1132P] where P = (Fo2 + 2Fc2)/3
3755 reflections	(Δ/σ)max = 0.001
273 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.19 e Å−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
S1	0.45270 (11)	0.85178 (9)	0.33662 (8)	0.0647 (3)
Cl1	0.61728 (16)	0.68418 (11)	0.47383 (9)	0.0975 (4)
O1	−0.0621 (2)	0.84964 (18)	0.10876 (17)	0.0450 (5)
O2	0.4577 (3)	1.0355 (2)	0.16837 (17)	0.0530 (6)
N1	−0.2014 (3)	0.7626 (2)	−0.0923 (2)	0.0434 (7)
N2	−0.1696 (3)	0.7554 (2)	−0.1953 (2)	0.0510 (7)
N3	0.2917 (3)	0.9627 (2)	0.1279 (2)	0.0479 (7)
N4	0.7640 (4)	0.8986 (3)	0.4813 (2)	0.0660 (9)
C1	−0.3633 (4)	0.7038 (3)	−0.0939 (3)	0.0471 (8)
C2	−0.4206 (4)	0.7326 (3)	0.0001 (3)	0.0636 (10)
H2	−0.3572	0.7937	0.0653	0.076*
C3	−0.5742 (5)	0.6692 (4)	−0.0040 (4)	0.0768 (12)
H3	−0.6126	0.6870	0.0599	0.092*
C4	−0.6702 (5)	0.5811 (4)	−0.0999 (5)	0.0914 (14)
H4	−0.7723	0.5384	−0.1009	0.110*
C5	−0.6157 (5)	0.5561 (4)	−0.1939 (4)	0.0941 (14)
H5	−0.6828	0.4975	−0.2602	0.113*
C6	−0.4610 (5)	0.6171 (4)	−0.1921 (3)	0.0719 (11)
H6	−0.4240	0.5994	−0.2566	0.086*
C7	0.0690 (4)	0.8267 (4)	−0.2568 (3)	0.0676 (11)
H7A	0.1699	0.7855	−0.2474	0.101*
H7B	0.1031	0.9108	−0.2490	0.101*
H7C	−0.0152	0.7919	−0.3324	0.101*
C8	−0.0104 (4)	0.8142 (3)	−0.1657 (3)	0.0465 (8)
C9	0.0656 (4)	0.8599 (3)	−0.0440 (2)	0.0400 (8)
C10	−0.0610 (4)	0.8238 (3)	−0.0019 (3)	0.0395 (8)
C11	−0.0066 (4)	0.7658 (3)	0.1735 (2)	0.0408 (8)
C12	−0.0280 (4)	0.7901 (3)	0.2804 (3)	0.0541 (9)
H12	−0.0762	0.8582	0.3055	0.065*
C13	0.0232 (4)	0.7116 (3)	0.3504 (3)	0.0591 (10)
H13	0.0085	0.7278	0.4230	0.071*
C14	0.0945 (4)	0.6111 (3)	0.3161 (3)	0.0531 (9)
C15	0.1125 (4)	0.5889 (3)	0.2072 (3)	0.0550 (9)
H15	0.1606	0.5209	0.1819	0.066*
C16	0.0612 (4)	0.6647 (3)	0.1352 (3)	0.0449 (8)
H16	0.0725	0.6474	0.0617	0.054*
C17	0.1474 (5)	0.5256 (4)	0.3933 (3)	0.0871 (13)
H17A	0.2202	0.5707	0.4695	0.131*
H17B	0.2110	0.4678	0.3609	0.131*
H17C	0.0447	0.4841	0.3984	0.131*
C18	0.2345 (4)	0.9303 (3)	0.0182 (3)	0.0437 (8)
H18	0.3035	0.9525	−0.0233	0.052*
C19	0.5031 (4)	1.0792 (3)	0.2911 (3)	0.0565 (9)
H19A	0.4004	1.1029	0.3096	0.068*
H19B	0.5904	1.1505	0.3175	0.068*
C20	0.5727 (4)	0.9879 (3)	0.3541 (3)	0.0468 (8)
C21	0.7309 (4)	0.9944 (4)	0.4334 (3)	0.0606 (10)
H21	0.8149	1.0620	0.4548	0.073*
C22	0.6282 (5)	0.8196 (4)	0.4373 (3)	0.0581 (10)

	U11	U22	U33	U12	U13	U23
S1	0.0518 (6)	0.0703 (7)	0.0665 (6)	−0.0003 (5)	0.0059 (5)	0.0280 (5)
Cl1	0.1287 (10)	0.0848 (9)	0.0856 (8)	0.0232 (7)	0.0255 (7)	0.0467 (7)
O1	0.0519 (13)	0.0432 (14)	0.0441 (13)	0.0105 (11)	0.0182 (11)	0.0148 (11)
O2	0.0445 (13)	0.0612 (16)	0.0491 (14)	−0.0041 (11)	0.0079 (11)	0.0191 (12)
N1	0.0359 (15)	0.0482 (18)	0.0457 (16)	0.0056 (13)	0.0095 (13)	0.0168 (14)
N2	0.0474 (17)	0.062 (2)	0.0428 (16)	0.0036 (15)	0.0121 (14)	0.0170 (14)
N3	0.0375 (15)	0.0513 (18)	0.0510 (18)	−0.0010 (13)	0.0074 (13)	0.0170 (14)
N4	0.062 (2)	0.077 (2)	0.0519 (19)	0.0171 (19)	0.0049 (16)	0.0184 (18)
C1	0.0368 (18)	0.041 (2)	0.065 (2)	0.0078 (16)	0.0136 (18)	0.0205 (18)
C2	0.049 (2)	0.073 (3)	0.073 (3)	0.005 (2)	0.026 (2)	0.019 (2)
C3	0.059 (3)	0.084 (3)	0.099 (3)	0.009 (2)	0.042 (2)	0.025 (3)
C4	0.058 (3)	0.072 (3)	0.150 (5)	−0.003 (2)	0.051 (3)	0.020 (3)
C5	0.057 (3)	0.080 (3)	0.118 (4)	−0.016 (2)	0.025 (3)	−0.017 (3)
C6	0.049 (2)	0.070 (3)	0.084 (3)	−0.002 (2)	0.022 (2)	−0.002 (2)
C7	0.069 (2)	0.089 (3)	0.050 (2)	−0.001 (2)	0.0227 (19)	0.027 (2)
C8	0.0408 (19)	0.053 (2)	0.048 (2)	0.0056 (17)	0.0118 (16)	0.0210 (17)
C9	0.0383 (18)	0.043 (2)	0.0402 (19)	0.0085 (15)	0.0097 (15)	0.0171 (16)
C10	0.0390 (18)	0.039 (2)	0.0418 (19)	0.0092 (15)	0.0118 (16)	0.0146 (16)
C11	0.0399 (17)	0.045 (2)	0.0403 (19)	0.0021 (16)	0.0149 (15)	0.0149 (16)
C12	0.067 (2)	0.053 (2)	0.050 (2)	0.0139 (19)	0.0300 (18)	0.0120 (18)
C13	0.072 (2)	0.064 (3)	0.047 (2)	0.004 (2)	0.0266 (19)	0.016 (2)
C14	0.060 (2)	0.049 (2)	0.058 (2)	0.0042 (19)	0.0227 (19)	0.0241 (19)
C15	0.059 (2)	0.049 (2)	0.064 (2)	0.0136 (18)	0.0257 (18)	0.0194 (19)
C16	0.0498 (19)	0.044 (2)	0.0461 (19)	0.0081 (17)	0.0217 (16)	0.0128 (17)
C17	0.116 (3)	0.080 (3)	0.084 (3)	0.021 (3)	0.038 (3)	0.050 (3)
C18	0.0398 (18)	0.050 (2)	0.049 (2)	0.0083 (16)	0.0161 (17)	0.0251 (17)
C19	0.053 (2)	0.057 (2)	0.050 (2)	0.0042 (18)	0.0068 (17)	0.0090 (19)
C20	0.0438 (19)	0.054 (2)	0.0397 (18)	0.0060 (17)	0.0121 (16)	0.0077 (17)
C21	0.054 (2)	0.065 (3)	0.051 (2)	0.0035 (19)	0.0053 (18)	0.011 (2)
C22	0.069 (2)	0.064 (3)	0.047 (2)	0.018 (2)	0.0207 (19)	0.020 (2)

S1—C22	1.708 (4)	C7—H7A	0.9600
S1—C20	1.718 (3)	C7—H7B	0.9600
Cl1—C22	1.714 (4)	C7—H7C	0.9600
O1—C10	1.352 (3)	C8—C9	1.414 (4)
O1—C11	1.397 (3)	C9—C10	1.370 (4)
O2—N3	1.421 (3)	C9—C18	1.436 (4)
O2—C19	1.424 (3)	C11—C16	1.368 (4)
N1—C10	1.351 (3)	C11—C12	1.370 (4)
N1—N2	1.375 (3)	C12—C13	1.384 (4)
N1—C1	1.430 (4)	C12—H12	0.9300
N2—C8	1.321 (4)	C13—C14	1.365 (5)
N3—C18	1.264 (4)	C13—H13	0.9300
N4—C22	1.272 (4)	C14—C15	1.383 (4)
N4—C21	1.365 (4)	C14—C17	1.512 (4)
C1—C2	1.374 (4)	C15—C16	1.377 (4)
C1—C6	1.374 (5)	C15—H15	0.9300
C2—C3	1.383 (5)	C16—H16	0.9300
C2—H2	0.9300	C17—H17A	0.9600
C3—C4	1.362 (6)	C17—H17B	0.9600
C3—H3	0.9300	C17—H17C	0.9600
C4—C5	1.358 (6)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.482 (4)
C5—C6	1.388 (5)	C19—H19A	0.9700
C5—H5	0.9300	C19—H19B	0.9700
C6—H6	0.9300	C20—C21	1.345 (4)
C7—C8	1.497 (4)	C21—H21	0.9300
C22—S1—C20	88.36 (18)	C16—C11—C12	120.9 (3)
C10—O1—C11	117.5 (2)	C16—C11—O1	124.2 (3)
N3—O2—C19	107.2 (2)	C12—C11—O1	114.9 (3)
C10—N1—N2	110.3 (2)	C11—C12—C13	118.9 (3)
C10—N1—C1	130.4 (3)	C11—C12—H12	120.6
N2—N1—C1	119.3 (3)	C13—C12—H12	120.6
C8—N2—N1	105.2 (2)	C14—C13—C12	121.9 (3)
C18—N3—O2	110.9 (2)	C14—C13—H13	119.0
C22—N4—C21	108.2 (3)	C12—C13—H13	119.0
C2—C1—C6	120.4 (3)	C13—C14—C15	117.6 (3)
C2—C1—N1	121.3 (3)	C13—C14—C17	121.1 (3)
C6—C1—N1	118.3 (3)	C15—C14—C17	121.3 (3)
C1—C2—C3	118.9 (4)	C16—C15—C14	121.8 (3)
C1—C2—H2	120.6	C16—C15—H15	119.1
C3—C2—H2	120.6	C14—C15—H15	119.1
C4—C3—C2	121.2 (4)	C11—C16—C15	118.9 (3)
C4—C3—H3	119.4	C11—C16—H16	120.5
C2—C3—H3	119.4	C15—C16—H16	120.5
C5—C4—C3	119.5 (4)	C14—C17—H17A	109.5
C5—C4—H4	120.3	C14—C17—H17B	109.5
C3—C4—H4	120.3	H17A—C17—H17B	109.5
C4—C5—C6	120.7 (4)	C14—C17—H17C	109.5
C4—C5—H5	119.6	H17A—C17—H17C	109.5
C6—C5—H5	119.6	H17B—C17—H17C	109.5
C1—C6—C5	119.2 (4)	N3—C18—C9	121.6 (3)
C1—C6—H6	120.4	N3—C18—H18	119.2
C5—C6—H6	120.4	C9—C18—H18	119.2
C8—C7—H7A	109.5	O2—C19—C20	112.5 (3)
C8—C7—H7B	109.5	O2—C19—H19A	109.1
H7A—C7—H7B	109.5	C20—C19—H19A	109.1
C8—C7—H7C	109.5	O2—C19—H19B	109.1
H7A—C7—H7C	109.5	C20—C19—H19B	109.1
H7B—C7—H7C	109.5	H19A—C19—H19B	107.8
N2—C8—C9	112.1 (3)	C21—C20—C19	128.5 (3)
N2—C8—C7	120.5 (3)	C21—C20—S1	108.3 (3)
C9—C8—C7	127.4 (3)	C19—C20—S1	123.1 (2)
C10—C9—C8	103.7 (3)	C20—C21—N4	117.8 (3)
C10—C9—C18	129.1 (3)	C20—C21—H21	121.1
C8—C9—C18	127.2 (3)	N4—C21—H21	121.1
N1—C10—O1	122.1 (3)	N4—C22—S1	117.4 (3)
N1—C10—C9	108.8 (3)	N4—C22—Cl1	122.8 (3)
O1—C10—C9	128.9 (3)	S1—C22—Cl1	119.9 (2)
C10—N1—N2—C8	−0.8 (3)	C8—C9—C10—O1	−175.4 (3)
C1—N1—N2—C8	−178.1 (2)	C18—C9—C10—O1	3.0 (5)
C19—O2—N3—C18	173.5 (3)	C10—O1—C11—C16	5.4 (4)
C10—N1—C1—C2	20.1 (5)	C10—O1—C11—C12	−173.3 (3)
N2—N1—C1—C2	−163.2 (3)	C16—C11—C12—C13	1.2 (5)
C10—N1—C1—C6	−159.8 (3)	O1—C11—C12—C13	179.9 (3)
N2—N1—C1—C6	16.9 (4)	C11—C12—C13—C14	0.1 (5)
C6—C1—C2—C3	2.8 (5)	C12—C13—C14—C15	−0.8 (5)
N1—C1—C2—C3	−177.1 (3)	C12—C13—C14—C17	−179.2 (3)
C1—C2—C3—C4	−1.3 (6)	C13—C14—C15—C16	0.1 (5)
C2—C3—C4—C5	−1.0 (7)	C17—C14—C15—C16	178.6 (3)
C3—C4—C5—C6	1.8 (7)	C12—C11—C16—C15	−1.8 (4)
C2—C1—C6—C5	−2.0 (5)	O1—C11—C16—C15	179.6 (3)
N1—C1—C6—C5	177.9 (3)	C14—C15—C16—C11	1.1 (5)
C4—C5—C6—C1	−0.3 (6)	O2—N3—C18—C9	−177.5 (2)
N1—N2—C8—C9	0.4 (3)	C10—C9—C18—N3	4.6 (5)
N1—N2—C8—C7	−179.3 (3)	C8—C9—C18—N3	−177.4 (3)
N2—C8—C9—C10	0.0 (3)	N3—O2—C19—C20	79.6 (3)
C7—C8—C9—C10	179.7 (3)	O2—C19—C20—C21	119.4 (3)
N2—C8—C9—C18	−178.4 (3)	O2—C19—C20—S1	−62.1 (3)
C7—C8—C9—C18	1.3 (5)	C22—S1—C20—C21	0.0 (2)
N2—N1—C10—O1	176.1 (3)	C22—S1—C20—C19	−178.9 (3)
C1—N1—C10—O1	−7.0 (5)	C19—C20—C21—N4	178.9 (3)
N2—N1—C10—C9	0.8 (3)	S1—C20—C21—N4	0.1 (4)
C1—N1—C10—C9	177.8 (3)	C22—N4—C21—C20	−0.2 (4)
C11—O1—C10—N1	90.5 (3)	C21—N4—C22—S1	0.1 (4)
C11—O1—C10—C9	−95.2 (4)	C21—N4—C22—Cl1	179.3 (2)
C8—C9—C10—N1	−0.5 (3)	C20—S1—C22—N4	−0.1 (3)
C18—C9—C10—N1	177.9 (3)	C20—S1—C22—Cl1	−179.3 (2)