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ISSN: 2056-9890

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

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[Ragavan, R. V., Vijayakumar, V. & Sucheta Kumari, N. (2009). Eur. J. Med. Chem. 44, 3852-3857.], 2010[Ragavan, R. V., Vijayakumar, V. & Sucheta Kumari, N. (2010). Eur. J. Med. Chem. 45, 1173-1180.]). For bond-length data, see: Allen et al. (1987[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.]). For a related structure, see: Loh et al. (2010[Loh, W.-S., Fun, H.-K., Ragavan, R. V., Vijayakumar, V. & Venkatesh, M. (2010). Acta Cryst. E66, o2563-o2564.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C22H17ClFN3O2S

  • Mr = 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[Bruker (2009). APEX2 SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.878, Tmax = 0.976

  • 30630 measured reflections

  • 4697 independent reflections

  • 3944 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.163

  • S = 1.24

  • 4697 reflections

  • 273 parameters

  • H-atom parameters constrained

  • Δρmax = 0.63 e Å−3

  • Δρmin = −0.53 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2009). APEX2 SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


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.

Refinement top

All H atoms were positioned geometrically with the bond length of C–H being 0.93 to 0.97 Å and were refined using a riding model, with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups.

Structure description 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.

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] 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
C22H17ClFN3O2SF(000) = 912
Mr = 441.90Dx = 1.422 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9879 reflections
a = 12.0296 (5) Åθ = 2.8–32.9°
b = 19.4428 (6) ŵ = 0.32 mm1
c = 9.5847 (3) ÅT = 100 K
β = 112.922 (1)°Plate, colourless
V = 2064.74 (12) Å30.42 × 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 tube3944 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
φ and ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS, Bruker, 2009)
h = 1515
Tmin = 0.878, Tmax = 0.976k = 2525
30630 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.24 w = 1/[σ2(Fo2) + (0.P)2 + 9.3055P]
where P = (Fo2 + 2Fc2)/3
4697 reflections(Δ/σ)max < 0.001
273 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = 0.53 e Å3
Crystal data top
C22H17ClFN3O2SV = 2064.74 (12) Å3
Mr = 441.90Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.0296 (5) ŵ = 0.32 mm1
b = 19.4428 (6) ÅT = 100 K
c = 9.5847 (3) Å0.42 × 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)
Tmin = 0.878, Tmax = 0.976Rint = 0.043
30630 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.163H-atom parameters constrained
S = 1.24Δρmax = 0.63 e Å3
4697 reflectionsΔρmin = 0.53 e Å3
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
xyzUiso*/Ueq
S10.28859 (8)0.28472 (4)0.01128 (10)0.0162 (2)
Cl10.24355 (9)0.04920 (5)0.40468 (12)0.0288 (2)
F10.2939 (2)0.38188 (13)0.2896 (3)0.0373 (6)
O10.4449 (2)0.36177 (13)0.1138 (3)0.0239 (6)
O20.5434 (2)0.27417 (14)0.1712 (3)0.0247 (6)
N10.0936 (3)0.24138 (15)0.0961 (3)0.0161 (6)
N20.0143 (3)0.21207 (15)0.1472 (3)0.0154 (6)
N30.3202 (3)0.15335 (15)0.0001 (4)0.0176 (6)
C10.0322 (3)0.14214 (17)0.1675 (4)0.0160 (7)
C20.1269 (3)0.12630 (18)0.1269 (4)0.0165 (7)
H2A0.16080.08320.12790.020*
C30.1616 (3)0.18936 (18)0.0837 (4)0.0164 (7)
C40.2558 (3)0.20259 (17)0.0272 (4)0.0155 (7)
C50.4011 (3)0.18060 (18)0.0546 (4)0.0178 (7)
C60.3963 (3)0.25092 (18)0.0694 (4)0.0165 (7)
C70.4701 (3)0.29491 (19)0.1238 (4)0.0185 (7)
C80.5145 (4)0.4118 (2)0.1592 (5)0.0281 (9)
H8A0.53290.39380.24220.034*
H8B0.58980.42200.07500.034*
C90.4385 (4)0.4758 (2)0.2080 (5)0.0326 (10)
H9A0.48610.51240.22290.049*
H9B0.40990.48870.13100.049*
H9C0.37080.46690.30100.049*
C100.4855 (4)0.1330 (2)0.0880 (5)0.0257 (9)
H10A0.47830.13990.19030.039*
H10B0.46540.08630.07540.039*
H10C0.56690.14240.01960.039*
C110.0686 (3)0.25574 (18)0.1786 (4)0.0150 (7)
C120.0298 (3)0.32104 (18)0.2356 (4)0.0179 (7)
H12A0.04740.33580.24980.021*
C130.1070 (3)0.36415 (19)0.2714 (4)0.0207 (8)
H13A0.08290.40830.30820.025*
C140.2197 (4)0.3401 (2)0.2510 (5)0.0247 (8)
C150.2614 (3)0.2759 (2)0.1924 (5)0.0242 (8)
H15A0.33830.26130.17960.029*
C160.1848 (3)0.2336 (2)0.1528 (4)0.0215 (8)
H16A0.21130.19080.10930.026*
C170.0370 (3)0.09629 (17)0.2271 (4)0.0162 (7)
C180.0471 (3)0.10914 (19)0.3647 (4)0.0207 (8)
H18A0.01050.14780.42080.025*
C190.1115 (3)0.06460 (19)0.4186 (5)0.0229 (8)
H19A0.11850.07320.51030.027*
C200.1653 (3)0.00709 (18)0.3334 (5)0.0205 (8)
C210.1571 (3)0.00729 (18)0.1970 (5)0.0217 (8)
H21A0.19390.04610.14160.026*
C220.0923 (3)0.03780 (18)0.1440 (4)0.0204 (8)
H22A0.08580.02890.05210.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0197 (4)0.0132 (4)0.0191 (5)0.0005 (3)0.0115 (3)0.0001 (3)
Cl10.0279 (5)0.0246 (5)0.0372 (6)0.0057 (4)0.0161 (4)0.0090 (4)
F10.0383 (14)0.0349 (14)0.0523 (18)0.0144 (11)0.0324 (13)0.0036 (12)
O10.0305 (14)0.0161 (12)0.0328 (16)0.0035 (11)0.0209 (13)0.0009 (11)
O20.0246 (14)0.0259 (14)0.0306 (16)0.0008 (11)0.0184 (12)0.0002 (12)
N10.0176 (14)0.0160 (14)0.0180 (16)0.0010 (11)0.0104 (12)0.0007 (12)
N20.0165 (14)0.0137 (14)0.0184 (16)0.0008 (11)0.0093 (12)0.0001 (11)
N30.0198 (14)0.0151 (14)0.0198 (17)0.0012 (11)0.0096 (12)0.0017 (12)
C10.0181 (16)0.0141 (16)0.0151 (18)0.0028 (13)0.0058 (13)0.0019 (13)
C20.0207 (17)0.0148 (16)0.0153 (18)0.0004 (13)0.0085 (14)0.0014 (13)
C30.0163 (16)0.0154 (16)0.0194 (19)0.0008 (12)0.0088 (14)0.0010 (13)
C40.0168 (16)0.0143 (16)0.0160 (18)0.0014 (12)0.0069 (13)0.0002 (13)
C50.0189 (17)0.0177 (16)0.0185 (19)0.0005 (13)0.0090 (14)0.0028 (14)
C60.0178 (16)0.0192 (17)0.0145 (18)0.0005 (13)0.0086 (14)0.0034 (13)
C70.0190 (17)0.0208 (17)0.0160 (19)0.0027 (13)0.0072 (14)0.0004 (14)
C80.031 (2)0.0214 (19)0.038 (3)0.0080 (16)0.0197 (19)0.0015 (17)
C90.034 (2)0.022 (2)0.040 (3)0.0068 (17)0.013 (2)0.0059 (18)
C100.0263 (19)0.0199 (18)0.038 (2)0.0011 (15)0.0207 (18)0.0050 (17)
C110.0191 (16)0.0188 (16)0.0097 (17)0.0032 (13)0.0084 (13)0.0027 (13)
C120.0187 (17)0.0179 (17)0.0174 (19)0.0013 (13)0.0074 (14)0.0022 (14)
C130.0302 (19)0.0203 (17)0.0136 (18)0.0050 (15)0.0105 (15)0.0018 (14)
C140.0262 (19)0.028 (2)0.026 (2)0.0118 (16)0.0168 (17)0.0062 (17)
C150.0183 (17)0.030 (2)0.027 (2)0.0033 (15)0.0113 (16)0.0083 (17)
C160.0192 (17)0.0217 (18)0.024 (2)0.0005 (14)0.0090 (15)0.0037 (15)
C170.0179 (16)0.0142 (16)0.0179 (19)0.0006 (13)0.0084 (14)0.0016 (13)
C180.0223 (18)0.0159 (16)0.024 (2)0.0039 (14)0.0097 (15)0.0008 (14)
C190.0252 (19)0.0219 (18)0.026 (2)0.0018 (15)0.0141 (16)0.0015 (15)
C200.0195 (17)0.0170 (17)0.027 (2)0.0014 (13)0.0115 (15)0.0067 (15)
C210.0246 (18)0.0139 (16)0.026 (2)0.0033 (14)0.0094 (16)0.0010 (15)
C220.0265 (19)0.0164 (17)0.021 (2)0.0020 (14)0.0121 (16)0.0028 (14)
Geometric parameters (Å, º) top
S1—C41.719 (3)C9—H9B0.9600
S1—C61.727 (3)C9—H9C0.9600
Cl1—C201.747 (4)C10—H10A0.9600
F1—C141.360 (4)C10—H10B0.9600
O1—C71.347 (4)C10—H10C0.9600
O1—C81.456 (4)C11—C121.389 (5)
O2—C71.207 (4)C11—C161.389 (5)
N1—C31.334 (4)C12—C131.389 (5)
N1—N21.356 (4)C12—H12A0.9300
N2—C11.378 (4)C13—C141.375 (5)
N2—C111.429 (4)C13—H13A0.9300
N3—C41.319 (4)C14—C151.380 (6)
N3—C51.378 (4)C15—C161.393 (5)
C1—C21.374 (5)C15—H15A0.9300
C1—C171.478 (5)C16—H16A0.9300
C2—C31.408 (5)C17—C181.394 (5)
C2—H2A0.9300C17—C221.399 (5)
C3—C41.457 (5)C18—C191.389 (5)
C5—C61.373 (5)C18—H18A0.9300
C5—C101.498 (5)C19—C201.387 (5)
C6—C71.467 (5)C19—H19A0.9300
C8—C91.507 (6)C20—C211.378 (6)
C8—H8A0.9700C21—C221.394 (5)
C8—H8B0.9700C21—H21A0.9300
C9—H9A0.9600C22—H22A0.9300
C4—S1—C688.81 (17)C5—C10—H10B109.5
C7—O1—C8116.8 (3)H10A—C10—H10B109.5
C3—N1—N2104.8 (3)C5—C10—H10C109.5
N1—N2—C1111.8 (3)H10A—C10—H10C109.5
N1—N2—C11118.3 (3)H10B—C10—H10C109.5
C1—N2—C11129.8 (3)C12—C11—C16120.9 (3)
C4—N3—C5110.6 (3)C12—C11—N2118.1 (3)
C2—C1—N2106.4 (3)C16—C11—N2121.0 (3)
C2—C1—C17128.9 (3)C13—C12—C11119.6 (3)
N2—C1—C17124.7 (3)C13—C12—H12A120.2
C1—C2—C3105.1 (3)C11—C12—H12A120.2
C1—C2—H2A127.4C14—C13—C12118.5 (4)
C3—C2—H2A127.4C14—C13—H13A120.8
N1—C3—C2111.8 (3)C12—C13—H13A120.8
N1—C3—C4119.4 (3)F1—C14—C13118.2 (4)
C2—C3—C4128.7 (3)F1—C14—C15118.6 (4)
N3—C4—C3123.1 (3)C13—C14—C15123.2 (3)
N3—C4—S1115.5 (3)C14—C15—C16118.1 (3)
C3—C4—S1121.4 (3)C14—C15—H15A120.9
C6—C5—N3114.5 (3)C16—C15—H15A120.9
C6—C5—C10126.7 (3)C11—C16—C15119.6 (4)
N3—C5—C10118.8 (3)C11—C16—H16A120.2
C5—C6—C7127.6 (3)C15—C16—H16A120.2
C5—C6—S1110.6 (3)C18—C17—C22119.1 (3)
C7—C6—S1121.8 (3)C18—C17—C1121.8 (3)
O2—C7—O1124.5 (3)C22—C17—C1119.0 (3)
O2—C7—C6124.8 (3)C19—C18—C17120.5 (3)
O1—C7—C6110.7 (3)C19—C18—H18A119.8
O1—C8—C9107.1 (3)C17—C18—H18A119.8
O1—C8—H8A110.3C20—C19—C18118.9 (4)
C9—C8—H8A110.3C20—C19—H19A120.6
O1—C8—H8B110.3C18—C19—H19A120.6
C9—C8—H8B110.3C21—C20—C19122.2 (3)
H8A—C8—H8B108.6C21—C20—Cl1119.5 (3)
C8—C9—H9A109.5C19—C20—Cl1118.3 (3)
C8—C9—H9B109.5C20—C21—C22118.4 (3)
H9A—C9—H9B109.5C20—C21—H21A120.8
C8—C9—H9C109.5C22—C21—H21A120.8
H9A—C9—H9C109.5C21—C22—C17120.9 (4)
H9B—C9—H9C109.5C21—C22—H22A119.6
C5—C10—H10A109.5C17—C22—H22A119.6
C3—N1—N2—C10.2 (4)C5—C6—C7—O1176.2 (4)
C3—N1—N2—C11177.3 (3)S1—C6—C7—O12.9 (4)
N1—N2—C1—C20.2 (4)C7—O1—C8—C9154.3 (4)
C11—N2—C1—C2176.9 (3)N1—N2—C11—C1234.4 (5)
N1—N2—C1—C17177.8 (3)C1—N2—C11—C12142.0 (4)
C11—N2—C1—C171.1 (6)N1—N2—C11—C16145.5 (3)
N2—C1—C2—C30.1 (4)C1—N2—C11—C1638.0 (5)
C17—C1—C2—C3177.8 (4)C16—C11—C12—C131.8 (5)
N2—N1—C3—C20.1 (4)N2—C11—C12—C13178.2 (3)
N2—N1—C3—C4178.5 (3)C11—C12—C13—C141.0 (5)
C1—C2—C3—N10.0 (4)C12—C13—C14—F1178.4 (3)
C1—C2—C3—C4178.5 (4)C12—C13—C14—C152.1 (6)
C5—N3—C4—C3179.1 (3)F1—C14—C15—C16179.8 (3)
C5—N3—C4—S10.0 (4)C13—C14—C15—C160.3 (6)
N1—C3—C4—N3174.4 (3)C12—C11—C16—C153.6 (6)
C2—C3—C4—N34.0 (6)N2—C11—C16—C15176.5 (3)
N1—C3—C4—S14.7 (5)C14—C15—C16—C112.5 (6)
C2—C3—C4—S1176.9 (3)C2—C1—C17—C18123.4 (4)
C6—S1—C4—N30.4 (3)N2—C1—C17—C1854.1 (5)
C6—S1—C4—C3178.8 (3)C2—C1—C17—C2255.6 (5)
C4—N3—C5—C60.4 (5)N2—C1—C17—C22126.9 (4)
C4—N3—C5—C10178.2 (3)C22—C17—C18—C190.2 (5)
N3—C5—C6—C7179.9 (3)C1—C17—C18—C19179.2 (3)
C10—C5—C6—C71.4 (7)C17—C18—C19—C200.2 (6)
N3—C5—C6—S10.7 (4)C18—C19—C20—C210.1 (6)
C10—C5—C6—S1177.8 (3)C18—C19—C20—Cl1178.8 (3)
C4—S1—C6—C50.6 (3)C19—C20—C21—C220.0 (6)
C4—S1—C6—C7179.8 (3)Cl1—C20—C21—C22178.9 (3)
C8—O1—C7—O22.1 (6)C20—C21—C22—C170.0 (6)
C8—O1—C7—C6178.0 (3)C18—C17—C22—C210.1 (5)
C5—C6—C7—O23.9 (6)C1—C17—C22—C21179.1 (3)
S1—C6—C7—O2177.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15A···O2i0.932.483.251 (5)141
Symmetry code: (i) x1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC22H17ClFN3O2S
Mr441.90
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)12.0296 (5), 19.4428 (6), 9.5847 (3)
β (°) 112.922 (1)
V3)2064.74 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.32
Crystal size (mm)0.42 × 0.17 × 0.08
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS, Bruker, 2009)
Tmin, Tmax0.878, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections
30630, 4697, 3944
Rint0.043
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.163, 1.24
No. of reflections4697
No. of parameters273
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C15—H15A···O2i0.932.483.251 (5)140.9
Symmetry code: (i) x1, 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

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