Ethyl 2-[5-(4-chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]-4-methyl­thia­zole-5-carboxyl­ate

Loh, W.-S.; Fun, H.-K.; Ragavan, R.V.; Vijayakumar, V.; Sarveswari, S.

doi:10.1107/S1600536810042066

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2925

https://doi.org/10.1107/S1600536810042066

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Ethyl 2-[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]-4-methylthiazole-5-carboxylate

Wan-Sin Loh,^a ‡ Hoong-Kun Fun,^a ^*§ R. Venkat Ragavan,^b V. Vijayakumar ^b and S. Sarveswari ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
^*Correspondence e-mail: hkfun@usm.my

(Received 13 October 2010; accepted 17 October 2010; online 23 October 2010)

In the title compound, C₂₂H₁₇ClFN₃O₂S, the pyrazole ring is approximately planar with a maximum deviation of 0.001 (4) Å and makes dihedral angles of 4.95 (19), 35.78 (18) and 54.73 (18)° with the thiazole, fluorobenzene and chlorobenzene rings, respectively. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into chains along the a axis.

Related literature

For background to pyrazole derivatives and their antimicrobial activity, see: Ragavan et al. (2009 , 2010 ). For bond-length data, see: Allen et al. (1987 ). For a related structure, see: Loh et al. (2010 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₂H₁₇ClFN₃O₂S
M_r = 441.90
Monoclinic, P 2₁ /c
a = 12.0296 (5) Å
b = 19.4428 (6) Å
c = 9.5847 (3) Å
β = 112.922 (1)°
V = 2064.74 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 100 K
0.42 × 0.17 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS, Bruker, 2009 ) T_min = 0.878, T_max = 0.976
30630 measured reflections
4697 independent reflections
3944 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.163
S = 1.24
4697 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2ⁱ	0.93	2.48	3.251 (5)	141
Symmetry code: (i) $[x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810042066/fj2354sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042066/fj2354Isup2.hkl

checkCIF report

Comment top

Antibacterial and antifungal activities of azoles are most widely studied and some of them are in clinical practice as anti-microbial agents. However, the azole-resistant strains had led to the development of new antimicrobial compounds. In particular pyrazole derivatives are extensively studied and used as antimicrobial agents. Pyrazole is an important class of heterocyclic compounds and many pyrazole derivatives are reported to have a broad spectrum of biological properties, such as anti-inflammatory, antifungal, herbicidal, anti-tumour, cytotoxic, molecular modelling and antiviral activities. Pyrazole derivatives also act as anti-angiogenic agents, A3 adenosine receptor antagonists, neuropeptide YY5 receptor antagonists, kinase inhibitor for treatment of type 2 diabetes, hyperlipidemia, obesity and thrombopiotinmimetics. Recently urea derivatives of pyrazoles have been reported as potent inhibitors of p38 kinase. Since the high electronegativity of halogens (particularly chlorine and fluorine) in the aromatic part of the drug molecules play an important role in enhancing their biological activity, we are interested to have 4-fluoro or 4-chloro substitution in the aryls of 1,5-diaryl pyrazoles. As part of our on-going research aiming the synthesis of new antimicrobial compounds, we have reported the synthesis of novel pyrazole derivatives and their microbial activities (Ragavan et al., 2009;2010).

The title compound consists of four rings, namely pyrazole (C1–C3/N1/N2), thiazole (C4/N3/C5/C6/S1), fluorophenyl (C11–C16/F1) and chlorophenyl (C17–C22/Cl1) rings (Fig. 1). The pyrazole ring is approximately planar with a maximum deviation of 0.001 (4) Å at atom C1 and makes dihedral angles of 4.95 (19), 35.78 (18) and 54.73 (18)° with the thiazole, fluorophenyl and chlorophenyl rings, respectively. Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structure (Loh et al., 2010).

In the crystal packing (Fig. 2), intermolecular C15—H15A···O2 hydrogen bonds link the molecules into one-dimensional chains along the a axis.

Related literature top

For background to pyrazole derivatives and their antimicrobial activity, see: Ragavan et al. (2009, 2010). For bond-length data, see: Allen et al. (1987). For a related structure, see: Loh et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The compound has been synthesized using the method available in the literature (Ragavan et al., 2010) and recrystallized using the ethanol-chloroform 1:1 mixture. Yield: 81%. M.p.: 411.3–413 K.

Structure description top

In the crystal packing (Fig. 2), intermolecular C15—H15A···O2 hydrogen bonds link the molecules into one-dimensional chains along the a axis.

For background to pyrazole derivatives and their antimicrobial activity, see: Ragavan et al. (2009, 2010). For bond-length data, see: Allen et al. (1987). For a related structure, see: Loh et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, showing one-dimensional chains along the a axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Ethyl 2-[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]-4- methylthiazole-5-carboxylate top

Crystal data top

C₂₂H₁₇ClFN₃O₂S	F(000) = 912
M_r = 441.90	D_x = 1.422 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9879 reflections
a = 12.0296 (5) Å	θ = 2.8–32.9°
b = 19.4428 (6) Å	µ = 0.32 mm⁻¹
c = 9.5847 (3) Å	T = 100 K
β = 112.922 (1)°	Plate, colourless
V = 2064.74 (12) Å³	0.42 × 0.17 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4697 independent reflections
Radiation source: fine-focus sealed tube	3944 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
φ and ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS, Bruker, 2009)	h = −15→15
T_min = 0.878, T_max = 0.976	k = −25→25
30630 measured reflections	l = −12→12

Refinement top

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.24	w = 1/[σ²(F_o²) + (0.P)² + 9.3055P] where P = (F_o² + 2F_c²)/3
4697 reflections	(Δ/σ)_max < 0.001
273 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₂₂H₁₇ClFN₃O₂S	V = 2064.74 (12) Å³
M_r = 441.90	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0296 (5) Å	µ = 0.32 mm⁻¹
b = 19.4428 (6) Å	T = 100 K
c = 9.5847 (3) Å	0.42 × 0.17 × 0.08 mm
β = 112.922 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4697 independent reflections
Absorption correction: multi-scan (SADABS, Bruker, 2009)	3944 reflections with I > 2σ(I)
T_min = 0.878, T_max = 0.976	R_int = 0.043
30630 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.24	Δρ_max = 0.63 e Å⁻³
4697 reflections	Δρ_min = −0.53 e Å⁻³
273 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
S1	0.28859 (8)	0.28472 (4)	−0.01128 (10)	0.0162 (2)
Cl1	−0.24355 (9)	−0.04920 (5)	0.40468 (12)	0.0288 (2)
F1	−0.2939 (2)	0.38188 (13)	0.2896 (3)	0.0373 (6)
O1	0.4449 (2)	0.36177 (13)	−0.1138 (3)	0.0239 (6)
O2	0.5434 (2)	0.27417 (14)	−0.1712 (3)	0.0247 (6)
N1	0.0936 (3)	0.24138 (15)	0.0961 (3)	0.0161 (6)
N2	0.0143 (3)	0.21207 (15)	0.1472 (3)	0.0154 (6)
N3	0.3202 (3)	0.15335 (15)	0.0001 (4)	0.0176 (6)
C1	0.0322 (3)	0.14214 (17)	0.1675 (4)	0.0160 (7)
C2	0.1269 (3)	0.12630 (18)	0.1269 (4)	0.0165 (7)
H2A	0.1608	0.0832	0.1279	0.020*
C3	0.1616 (3)	0.18936 (18)	0.0837 (4)	0.0164 (7)
C4	0.2558 (3)	0.20259 (17)	0.0272 (4)	0.0155 (7)
C5	0.4011 (3)	0.18060 (18)	−0.0546 (4)	0.0178 (7)
C6	0.3963 (3)	0.25092 (18)	−0.0694 (4)	0.0165 (7)
C7	0.4701 (3)	0.29491 (19)	−0.1238 (4)	0.0185 (7)
C8	0.5145 (4)	0.4118 (2)	−0.1592 (5)	0.0281 (9)
H8A	0.5329	0.3938	−0.2422	0.034*
H8B	0.5898	0.4220	−0.0750	0.034*
C9	0.4385 (4)	0.4758 (2)	−0.2080 (5)	0.0326 (10)
H9A	0.4861	0.5124	−0.2229	0.049*
H9B	0.4099	0.4887	−0.1310	0.049*
H9C	0.3708	0.4669	−0.3010	0.049*
C10	0.4855 (4)	0.1330 (2)	−0.0880 (5)	0.0257 (9)
H10A	0.4783	0.1399	−0.1903	0.039*
H10B	0.4654	0.0863	−0.0754	0.039*
H10C	0.5669	0.1424	−0.0196	0.039*
C11	−0.0686 (3)	0.25574 (18)	0.1786 (4)	0.0150 (7)
C12	−0.0298 (3)	0.32104 (18)	0.2356 (4)	0.0179 (7)
H12A	0.0474	0.3358	0.2498	0.021*
C13	−0.1070 (3)	0.36415 (19)	0.2714 (4)	0.0207 (8)
H13A	−0.0829	0.4083	0.3082	0.025*
C14	−0.2197 (4)	0.3401 (2)	0.2510 (5)	0.0247 (8)
C15	−0.2614 (3)	0.2759 (2)	0.1924 (5)	0.0242 (8)
H15A	−0.3383	0.2613	0.1796	0.029*
C16	−0.1848 (3)	0.2336 (2)	0.1528 (4)	0.0215 (8)
H16A	−0.2113	0.1908	0.1093	0.026*
C17	−0.0370 (3)	0.09629 (17)	0.2271 (4)	0.0162 (7)
C18	−0.0471 (3)	0.10914 (19)	0.3647 (4)	0.0207 (8)
H18A	−0.0105	0.1478	0.4208	0.025*
C19	−0.1115 (3)	0.06460 (19)	0.4186 (5)	0.0229 (8)
H19A	−0.1185	0.0732	0.5103	0.027*
C20	−0.1653 (3)	0.00709 (18)	0.3334 (5)	0.0205 (8)
C21	−0.1571 (3)	−0.00729 (18)	0.1970 (5)	0.0217 (8)
H21A	−0.1939	−0.0461	0.1416	0.026*
C22	−0.0923 (3)	0.03780 (18)	0.1440 (4)	0.0204 (8)
H22A	−0.0858	0.0289	0.0521	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0197 (4)	0.0132 (4)	0.0191 (5)	0.0005 (3)	0.0115 (3)	−0.0001 (3)
Cl1	0.0279 (5)	0.0246 (5)	0.0372 (6)	−0.0057 (4)	0.0161 (4)	0.0090 (4)
F1	0.0383 (14)	0.0349 (14)	0.0523 (18)	0.0144 (11)	0.0324 (13)	0.0036 (12)
O1	0.0305 (14)	0.0161 (12)	0.0328 (16)	−0.0035 (11)	0.0209 (13)	0.0009 (11)
O2	0.0246 (14)	0.0259 (14)	0.0306 (16)	−0.0008 (11)	0.0184 (12)	0.0002 (12)
N1	0.0176 (14)	0.0160 (14)	0.0180 (16)	−0.0010 (11)	0.0104 (12)	0.0007 (12)
N2	0.0165 (14)	0.0137 (14)	0.0184 (16)	−0.0008 (11)	0.0093 (12)	−0.0001 (11)
N3	0.0198 (14)	0.0151 (14)	0.0198 (17)	−0.0012 (11)	0.0096 (12)	−0.0017 (12)
C1	0.0181 (16)	0.0141 (16)	0.0151 (18)	−0.0028 (13)	0.0058 (13)	−0.0019 (13)
C2	0.0207 (17)	0.0148 (16)	0.0153 (18)	−0.0004 (13)	0.0085 (14)	−0.0014 (13)
C3	0.0163 (16)	0.0154 (16)	0.0194 (19)	−0.0008 (12)	0.0088 (14)	−0.0010 (13)
C4	0.0168 (16)	0.0143 (16)	0.0160 (18)	−0.0014 (12)	0.0069 (13)	−0.0002 (13)
C5	0.0189 (17)	0.0177 (16)	0.0185 (19)	−0.0005 (13)	0.0090 (14)	−0.0028 (14)
C6	0.0178 (16)	0.0192 (17)	0.0145 (18)	−0.0005 (13)	0.0086 (14)	−0.0034 (13)
C7	0.0190 (17)	0.0208 (17)	0.0160 (19)	−0.0027 (13)	0.0072 (14)	−0.0004 (14)
C8	0.031 (2)	0.0214 (19)	0.038 (3)	−0.0080 (16)	0.0197 (19)	0.0015 (17)
C9	0.034 (2)	0.022 (2)	0.040 (3)	−0.0068 (17)	0.013 (2)	0.0059 (18)
C10	0.0263 (19)	0.0199 (18)	0.038 (2)	0.0011 (15)	0.0207 (18)	−0.0050 (17)
C11	0.0191 (16)	0.0188 (16)	0.0097 (17)	0.0032 (13)	0.0084 (13)	0.0027 (13)
C12	0.0187 (17)	0.0179 (17)	0.0174 (19)	0.0013 (13)	0.0074 (14)	0.0022 (14)
C13	0.0302 (19)	0.0203 (17)	0.0136 (18)	0.0050 (15)	0.0105 (15)	0.0018 (14)
C14	0.0262 (19)	0.028 (2)	0.026 (2)	0.0118 (16)	0.0168 (17)	0.0062 (17)
C15	0.0183 (17)	0.030 (2)	0.027 (2)	0.0033 (15)	0.0113 (16)	0.0083 (17)
C16	0.0192 (17)	0.0217 (18)	0.024 (2)	−0.0005 (14)	0.0090 (15)	0.0037 (15)
C17	0.0179 (16)	0.0142 (16)	0.0179 (19)	0.0006 (13)	0.0084 (14)	0.0016 (13)
C18	0.0223 (18)	0.0159 (16)	0.024 (2)	−0.0039 (14)	0.0097 (15)	−0.0008 (14)
C19	0.0252 (19)	0.0219 (18)	0.026 (2)	−0.0018 (15)	0.0141 (16)	0.0015 (15)
C20	0.0195 (17)	0.0170 (17)	0.027 (2)	−0.0014 (13)	0.0115 (15)	0.0067 (15)
C21	0.0246 (18)	0.0139 (16)	0.026 (2)	−0.0033 (14)	0.0094 (16)	−0.0010 (15)
C22	0.0265 (19)	0.0164 (17)	0.021 (2)	−0.0020 (14)	0.0121 (16)	−0.0028 (14)

Geometric parameters (Å, º) top

S1—C4	1.719 (3)	C9—H9B	0.9600
S1—C6	1.727 (3)	C9—H9C	0.9600
Cl1—C20	1.747 (4)	C10—H10A	0.9600
F1—C14	1.360 (4)	C10—H10B	0.9600
O1—C7	1.347 (4)	C10—H10C	0.9600
O1—C8	1.456 (4)	C11—C12	1.389 (5)
O2—C7	1.207 (4)	C11—C16	1.389 (5)
N1—C3	1.334 (4)	C12—C13	1.389 (5)
N1—N2	1.356 (4)	C12—H12A	0.9300
N2—C1	1.378 (4)	C13—C14	1.375 (5)
N2—C11	1.429 (4)	C13—H13A	0.9300
N3—C4	1.319 (4)	C14—C15	1.380 (6)
N3—C5	1.378 (4)	C15—C16	1.393 (5)
C1—C2	1.374 (5)	C15—H15A	0.9300
C1—C17	1.478 (5)	C16—H16A	0.9300
C2—C3	1.408 (5)	C17—C18	1.394 (5)
C2—H2A	0.9300	C17—C22	1.399 (5)
C3—C4	1.457 (5)	C18—C19	1.389 (5)
C5—C6	1.373 (5)	C18—H18A	0.9300
C5—C10	1.498 (5)	C19—C20	1.387 (5)
C6—C7	1.467 (5)	C19—H19A	0.9300
C8—C9	1.507 (6)	C20—C21	1.378 (6)
C8—H8A	0.9700	C21—C22	1.394 (5)
C8—H8B	0.9700	C21—H21A	0.9300
C9—H9A	0.9600	C22—H22A	0.9300

C4—S1—C6	88.81 (17)	C5—C10—H10B	109.5
C7—O1—C8	116.8 (3)	H10A—C10—H10B	109.5
C3—N1—N2	104.8 (3)	C5—C10—H10C	109.5
N1—N2—C1	111.8 (3)	H10A—C10—H10C	109.5
N1—N2—C11	118.3 (3)	H10B—C10—H10C	109.5
C1—N2—C11	129.8 (3)	C12—C11—C16	120.9 (3)
C4—N3—C5	110.6 (3)	C12—C11—N2	118.1 (3)
C2—C1—N2	106.4 (3)	C16—C11—N2	121.0 (3)
C2—C1—C17	128.9 (3)	C13—C12—C11	119.6 (3)
N2—C1—C17	124.7 (3)	C13—C12—H12A	120.2
C1—C2—C3	105.1 (3)	C11—C12—H12A	120.2
C1—C2—H2A	127.4	C14—C13—C12	118.5 (4)
C3—C2—H2A	127.4	C14—C13—H13A	120.8
N1—C3—C2	111.8 (3)	C12—C13—H13A	120.8
N1—C3—C4	119.4 (3)	F1—C14—C13	118.2 (4)
C2—C3—C4	128.7 (3)	F1—C14—C15	118.6 (4)
N3—C4—C3	123.1 (3)	C13—C14—C15	123.2 (3)
N3—C4—S1	115.5 (3)	C14—C15—C16	118.1 (3)
C3—C4—S1	121.4 (3)	C14—C15—H15A	120.9
C6—C5—N3	114.5 (3)	C16—C15—H15A	120.9
C6—C5—C10	126.7 (3)	C11—C16—C15	119.6 (4)
N3—C5—C10	118.8 (3)	C11—C16—H16A	120.2
C5—C6—C7	127.6 (3)	C15—C16—H16A	120.2
C5—C6—S1	110.6 (3)	C18—C17—C22	119.1 (3)
C7—C6—S1	121.8 (3)	C18—C17—C1	121.8 (3)
O2—C7—O1	124.5 (3)	C22—C17—C1	119.0 (3)
O2—C7—C6	124.8 (3)	C19—C18—C17	120.5 (3)
O1—C7—C6	110.7 (3)	C19—C18—H18A	119.8
O1—C8—C9	107.1 (3)	C17—C18—H18A	119.8
O1—C8—H8A	110.3	C20—C19—C18	118.9 (4)
C9—C8—H8A	110.3	C20—C19—H19A	120.6
O1—C8—H8B	110.3	C18—C19—H19A	120.6
C9—C8—H8B	110.3	C21—C20—C19	122.2 (3)
H8A—C8—H8B	108.6	C21—C20—Cl1	119.5 (3)
C8—C9—H9A	109.5	C19—C20—Cl1	118.3 (3)
C8—C9—H9B	109.5	C20—C21—C22	118.4 (3)
H9A—C9—H9B	109.5	C20—C21—H21A	120.8
C8—C9—H9C	109.5	C22—C21—H21A	120.8
H9A—C9—H9C	109.5	C21—C22—C17	120.9 (4)
H9B—C9—H9C	109.5	C21—C22—H22A	119.6
C5—C10—H10A	109.5	C17—C22—H22A	119.6

C3—N1—N2—C1	0.2 (4)	C5—C6—C7—O1	−176.2 (4)
C3—N1—N2—C11	177.3 (3)	S1—C6—C7—O1	2.9 (4)
N1—N2—C1—C2	−0.2 (4)	C7—O1—C8—C9	154.3 (4)
C11—N2—C1—C2	−176.9 (3)	N1—N2—C11—C12	−34.4 (5)
N1—N2—C1—C17	177.8 (3)	C1—N2—C11—C12	142.0 (4)
C11—N2—C1—C17	1.1 (6)	N1—N2—C11—C16	145.5 (3)
N2—C1—C2—C3	0.1 (4)	C1—N2—C11—C16	−38.0 (5)
C17—C1—C2—C3	−177.8 (4)	C16—C11—C12—C13	1.8 (5)
N2—N1—C3—C2	−0.1 (4)	N2—C11—C12—C13	−178.2 (3)
N2—N1—C3—C4	178.5 (3)	C11—C12—C13—C14	1.0 (5)
C1—C2—C3—N1	0.0 (4)	C12—C13—C14—F1	178.4 (3)
C1—C2—C3—C4	−178.5 (4)	C12—C13—C14—C15	−2.1 (6)
C5—N3—C4—C3	179.1 (3)	F1—C14—C15—C16	179.8 (3)
C5—N3—C4—S1	0.0 (4)	C13—C14—C15—C16	0.3 (6)
N1—C3—C4—N3	−174.4 (3)	C12—C11—C16—C15	−3.6 (6)
C2—C3—C4—N3	4.0 (6)	N2—C11—C16—C15	176.5 (3)
N1—C3—C4—S1	4.7 (5)	C14—C15—C16—C11	2.5 (6)
C2—C3—C4—S1	−176.9 (3)	C2—C1—C17—C18	123.4 (4)
C6—S1—C4—N3	0.4 (3)	N2—C1—C17—C18	−54.1 (5)
C6—S1—C4—C3	−178.8 (3)	C2—C1—C17—C22	−55.6 (5)
C4—N3—C5—C6	−0.4 (5)	N2—C1—C17—C22	126.9 (4)
C4—N3—C5—C10	178.2 (3)	C22—C17—C18—C19	−0.2 (5)
N3—C5—C6—C7	179.9 (3)	C1—C17—C18—C19	−179.2 (3)
C10—C5—C6—C7	1.4 (7)	C17—C18—C19—C20	0.2 (6)
N3—C5—C6—S1	0.7 (4)	C18—C19—C20—C21	−0.1 (6)
C10—C5—C6—S1	−177.8 (3)	C18—C19—C20—Cl1	178.8 (3)
C4—S1—C6—C5	−0.6 (3)	C19—C20—C21—C22	0.0 (6)
C4—S1—C6—C7	−179.8 (3)	Cl1—C20—C21—C22	−178.9 (3)
C8—O1—C7—O2	−2.1 (6)	C20—C21—C22—C17	0.0 (6)
C8—O1—C7—C6	178.0 (3)	C18—C17—C22—C21	0.1 (5)
C5—C6—C7—O2	3.9 (6)	C1—C17—C22—C21	179.1 (3)
S1—C6—C7—O2	−177.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2ⁱ	0.93	2.48	3.251 (5)	141

Symmetry code: (i) x−1, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇ClFN₃O₂S
M_r	441.90
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.0296 (5), 19.4428 (6), 9.5847 (3)
β (°)	112.922 (1)
V (Å³)	2064.74 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.42 × 0.17 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS, Bruker, 2009)
T_min, T_max	0.878, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	30630, 4697, 3944
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.163, 1.24
No. of reflections	4697
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.53

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2ⁱ	0.93	2.48	3.251 (5)	140.9

Symmetry code: (i) x−1, −y+1/2, z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: C-7581-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL thanks Malaysian Government and USM for the award of Research Fellowship. VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2009). APEX2 SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Loh, W.-S., Fun, H.-K., Ragavan, R. V., Vijayakumar, V. & Venkatesh, M. (2010). Acta Cryst. E66, o2563–o2564. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ragavan, R. V., Vijayakumar, V. & Sucheta Kumari, N. (2009). Eur. J. Med. Chem. 44, 3852–3857. PubMed CAS Google Scholar
Ragavan, R. V., Vijayakumar, V. & Sucheta Kumari, N. (2010). Eur. J. Med. Chem. 45, 1173–1180. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

Ethyl 2-[5-(4-chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]-4-methyl­thia­zole-5-carboxyl­ate

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Ethyl 2-[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]-4-methylthiazole-5-carboxylate