2-[5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole

Abdel-Wahab, B.F.; Mohamed, H.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536813004339

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 3| March 2013| Pages o392-o393

doi:10.1107/S1600536813004339

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2-[5-(4-Fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thiazole

Bakr F. Abdel-Wahab,^a ‡ Hanan A. Mohamed,^a Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 13 February 2013; accepted 13 February 2013; online 16 February 2013)

In the title compound, C₂₅H₂₀FN₃S, two independent molecules comprise the asymmetric unit, which differ in the relative orientation of the fluorobenzene ring with respect to the pyrazole ring to which it is attached [dihedral angles = 89.39 (17) and 75.23 (16)° in the two molecules]. Each pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. There are additional twists in the molecules, e.g. between the five-membered rings [dihedral angles = 18.23 (16) and 17.84 (16)°] and between the thiazole and attached phenyl ring [10.26 (16) and 20.87 (15)°]. Overall, each molecule has a T-shape. In the crystal, molecules are connected into a three-dimensional architecture by weak C—H⋯π interactions.

Related literature

For the biological activity of pyrazolin-1-ylthiazoles, see: Abdel-Wahab et al. (2009 , 2012 ); Chimenti et al. (2010 ). For a related structure, see: Fun et al. (2011 ).

Experimental

Crystal data

C₂₅H₂₀FN₃S
M_r = 413.50
Monoclinic, P c
a = 5.7563 (3) Å
b = 24.1214 (12) Å
c = 15.1827 (8) Å
β = 90.948 (5)°
V = 2107.83 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 295 K
0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.837, T_max = 1.000
22651 measured reflections
9054 independent reflections
5841 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.117
S = 0.99
9054 reflections
543 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), 4165 Friedel pairs
Flack parameter: −0.06 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C26–C31, C45–C50, S2,N4,C32–C34 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯Cg1	0.93	2.75	3.537 (3)	143
C19—H19A⋯Cg2ⁱ	0.96	2.94	3.596 (4)	127
C35—H35⋯Cg3ⁱⁱ	0.98	2.94	3.843 (3)	153
C42—H42⋯Cg4ⁱⁱⁱ	0.93	2.86	3.567 (3)	134
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ), QMol (Gans & Shalloway, 2001 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813004339/hg5292sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004339/hg5292Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813004339/hg5292Isup3.cml

checkCIF report

Comment top

The title compound (I) was investigated in relation to the established biological activities exhibited by pyrazolin-1-ylthiazoles (Abdel-Wahab et al., 2012; Abdel-Wahab et al., 2009; Chimenti et al., 2010).

Two independent molecules comprise the crystallographic asymmetric unit of (I), Fig. 1. As judged from the overlay diagram, Fig. 2, the central residues are super-imposable with the major difference relating to the relative orientations of the fluorobenzene rings with the dihedral angle formed with the least-squares plane through the pyrazolyl ring being 89.39 (17)° for the S1-containing molecule and 75.23 (16)° for the second molecule. Each pyrazolyl ring adopts an envelope conformation with the methine-C atom, i.e. C10 and C35, being the flap atom in each case. With the exception of the near perpendicular relationship between the pyrazolyl and fluorobenzene rings, the remaining components of the molecule exhibit relatively small twists as indicated by the dihedral angles formed between the five-membered rings [18.23 (16); 17.84 (16)°], the thiazolyl and attached phenyl ring [10.26 (16); 20.87 (15)°], and between the pyrazolyl and appended tolyl ring [2.37 (16); 1.96 (16)°]. Overall, the molecule has the shape of the letter T and resembles the structure of a literature precedent (Fun et al., 2011).

The crystal packing is dominated by C—H···π interactions that lead to a three-dimensional architecture, Fig. 3 and Table 1.

Related literature top

For the biological activity of pyrazolin-1-ylthiazoles, see: Abdel-Wahab et al. (2009, 2012); Chimenti et al. (2010). For a related structure, see: Fun et al. (2011).

Experimental top

A mixture of 5-(4-fluorophenyl)-3-p-tolyl-4,5-dihydro-1H-pyrazole-1-carbothioamide (0.31 g, 0.001 M) and 2-bromo-1-phenylethanone (0.2 g, 0.001 M) in anhydrous ethanol (30 ml) was heated under reflux for about 4 h. The resultant solid was filtered and dried. Re-crystallization was by slow evaporation of a DMF solution of (I) which yielded colourless crystals in 59% yield. M.pt. 418–420 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.
	Fig. 2. Overlay diagram of the two independent molecules in (I) with the S1-containing molecule illustrated in red. The molecules are overlaid so that the thiazolyl rings are superimposed.
	Fig. 3. A view of the crystal packing in projection down the a axis. The C—H···π interactions are shown as purple dashed lines.

2-[5-(4-Fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thiazole top

Crystal data top

C₂₅H₂₀FN₃S	F(000) = 864
M_r = 413.50	D_x = 1.303 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 5001 reflections
a = 5.7563 (3) Å	θ = 2.9–27.5°
b = 24.1214 (12) Å	µ = 0.18 mm⁻¹
c = 15.1827 (8) Å	T = 295 K
β = 90.948 (5)°	Prism, yellow
V = 2107.83 (19) Å³	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	9054 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5841 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.042
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.9°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −31→31
T_min = 0.837, T_max = 1.000	l = −19→19
22651 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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0492P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
9054 reflections	Δρ_max = 0.14 e Å⁻³
543 parameters	Δρ_min = −0.16 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 4165 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (6)

Crystal data top

C₂₅H₂₀FN₃S	V = 2107.83 (19) Å³
M_r = 413.50	Z = 4
Monoclinic, Pc	Mo Kα radiation
a = 5.7563 (3) Å	µ = 0.18 mm⁻¹
b = 24.1214 (12) Å	T = 295 K
c = 15.1827 (8) Å	0.40 × 0.30 × 0.20 mm
β = 90.948 (5)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	9054 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	5841 reflections with I > 2σ(I)
T_min = 0.837, T_max = 1.000	R_int = 0.042
22651 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.117	Δρ_max = 0.14 e Å⁻³
S = 0.99	Δρ_min = −0.16 e Å⁻³
9054 reflections	Absolute structure: Flack (1983), 4165 Friedel pairs
543 parameters	Absolute structure parameter: −0.06 (6)
2 restraints

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
S1	0.49969 (14)	0.29737 (3)	0.50008 (6)	0.0662 (2)
S2	1.01138 (13)	0.25628 (3)	0.36822 (6)	0.0666 (2)
F1	−0.0507 (5)	0.34215 (9)	0.99078 (17)	0.1149 (8)
F2	0.5094 (5)	0.12749 (9)	−0.12101 (16)	0.1042 (7)
N1	0.1354 (4)	0.32997 (10)	0.58332 (16)	0.0579 (6)
N2	0.2741 (4)	0.24238 (11)	0.62782 (17)	0.0638 (7)
N3	0.4085 (4)	0.19780 (11)	0.60017 (17)	0.0621 (7)
N4	0.8192 (4)	0.17483 (10)	0.28401 (16)	0.0585 (6)
N5	0.6904 (4)	0.26272 (10)	0.23727 (18)	0.0635 (7)
N6	0.6916 (4)	0.31858 (10)	0.26139 (16)	0.0590 (7)
C1	0.0526 (5)	0.42283 (12)	0.52259 (19)	0.0571 (8)
C2	0.1262 (6)	0.46954 (15)	0.4761 (2)	0.0740 (9)
H2A	0.2631	0.4680	0.4445	0.089*
C3	−0.0020 (7)	0.51781 (16)	0.4767 (3)	0.0822 (11)
H3	0.0519	0.5489	0.4470	0.099*
C4	−0.2069 (7)	0.52053 (16)	0.5204 (3)	0.0835 (11)
H4	−0.2947	0.5529	0.5192	0.100*
C5	−0.2824 (6)	0.47491 (16)	0.5663 (2)	0.0758 (10)
H5	−0.4214	0.4766	0.5965	0.091*
C6	−0.1532 (6)	0.42654 (14)	0.5678 (2)	0.0653 (8)
H6	−0.2055	0.3962	0.5995	0.078*
C7	0.1944 (5)	0.37188 (12)	0.52465 (19)	0.0554 (7)
C8	0.3820 (6)	0.36115 (13)	0.4756 (2)	0.0643 (8)
H8	0.4406	0.3853	0.4336	0.077*
C9	0.2832 (5)	0.28972 (13)	0.57623 (19)	0.0559 (7)
C10	0.0630 (5)	0.22505 (13)	0.6747 (2)	0.0606 (8)
H10	−0.0735	0.2297	0.6360	0.073*
C11	0.1131 (6)	0.16282 (13)	0.6878 (2)	0.0664 (9)
H11A	0.1453	0.1544	0.7493	0.080*
H11B	−0.0168	0.1404	0.6673	0.080*
C12	0.3231 (5)	0.15310 (13)	0.6329 (2)	0.0569 (7)
C13	0.4368 (5)	0.09940 (13)	0.61754 (19)	0.0566 (7)
C14	0.6347 (5)	0.09546 (14)	0.5673 (2)	0.0640 (8)
H14	0.6926	0.1270	0.5402	0.077*
C15	0.7465 (6)	0.04580 (14)	0.5568 (2)	0.0671 (9)
H15	0.8800	0.0445	0.5232	0.081*
C16	0.6653 (5)	−0.00304 (13)	0.5954 (2)	0.0618 (8)
C17	0.4650 (6)	0.00095 (14)	0.6425 (2)	0.0659 (8)
H17	0.4040	−0.0309	0.6677	0.079*
C18	0.3500 (6)	0.05102 (14)	0.6539 (2)	0.0652 (8)
H18	0.2140	0.0521	0.6861	0.078*
C19	0.7985 (6)	−0.05603 (14)	0.5865 (3)	0.0827 (11)
H19A	0.7180	−0.0853	0.6161	0.124*
H19B	0.9506	−0.0516	0.6125	0.124*
H19C	0.8123	−0.0651	0.5253	0.124*
C20	0.0305 (5)	0.25749 (12)	0.7580 (2)	0.0542 (7)
C21	0.1996 (5)	0.25682 (13)	0.8234 (2)	0.0637 (8)
H21	0.3345	0.2365	0.8146	0.076*
C22	0.1749 (7)	0.28550 (14)	0.9016 (2)	0.0733 (9)
H22	0.2902	0.2844	0.9452	0.088*
C23	−0.0195 (7)	0.31483 (13)	0.9126 (2)	0.0731 (10)
C24	−0.1901 (7)	0.31738 (15)	0.8503 (3)	0.0816 (11)
H24	−0.3236	0.3380	0.8603	0.098*
C25	−0.1649 (6)	0.28920 (14)	0.7719 (3)	0.0709 (9)
H25	−0.2800	0.2916	0.7284	0.085*
C26	1.0106 (5)	0.09110 (13)	0.34701 (18)	0.0561 (7)
C27	1.2113 (6)	0.06737 (16)	0.3842 (2)	0.0696 (9)
H27	1.3308	0.0901	0.4048	0.084*
C28	1.2335 (6)	0.01085 (17)	0.3907 (2)	0.0775 (10)
H28	1.3676	−0.0043	0.4157	0.093*
C29	1.0595 (6)	−0.02337 (15)	0.3605 (2)	0.0737 (10)
H29	1.0758	−0.0617	0.3645	0.088*
C30	0.8601 (6)	−0.00060 (15)	0.3242 (2)	0.0731 (9)
H30	0.7405	−0.0236	0.3045	0.088*
C31	0.8373 (6)	0.05605 (13)	0.3171 (2)	0.0643 (8)
H31	0.7029	0.0709	0.2917	0.077*
C32	0.9822 (5)	0.15215 (13)	0.34277 (19)	0.0551 (7)
C33	1.0981 (6)	0.18976 (14)	0.3925 (2)	0.0644 (8)
H33	1.2110	0.1808	0.4347	0.077*
C34	0.8228 (5)	0.22829 (13)	0.2909 (2)	0.0550 (7)
C35	0.4651 (5)	0.24534 (12)	0.1964 (2)	0.0559 (8)
H35	0.3740	0.2246	0.2392	0.067*
C36	0.3531 (5)	0.30230 (12)	0.1797 (2)	0.0619 (8)
H36A	0.3483	0.3109	0.1173	0.074*
H36B	0.1964	0.3034	0.2021	0.074*
C37	0.5083 (5)	0.34182 (12)	0.22889 (19)	0.0544 (7)
C38	0.4623 (5)	0.40098 (12)	0.23963 (19)	0.0531 (7)
C39	0.6205 (5)	0.43590 (13)	0.2823 (2)	0.0608 (8)
H39	0.7594	0.4216	0.3046	0.073*
C40	0.5724 (6)	0.49193 (13)	0.2918 (2)	0.0673 (9)
H40	0.6797	0.5146	0.3207	0.081*
C41	0.3681 (6)	0.51480 (13)	0.2591 (2)	0.0619 (8)
C42	0.2136 (6)	0.48056 (13)	0.2167 (2)	0.0646 (8)
H42	0.0760	0.4952	0.1938	0.077*
C43	0.2585 (5)	0.42450 (12)	0.2075 (2)	0.0629 (8)
H43	0.1493	0.4021	0.1790	0.075*
C44	0.3189 (8)	0.57637 (13)	0.2676 (3)	0.0901 (12)
H44A	0.3506	0.5880	0.3270	0.135*
H44B	0.1588	0.5834	0.2529	0.135*
H44C	0.4163	0.5966	0.2281	0.135*
C45	0.4915 (5)	0.21170 (11)	0.1141 (2)	0.0520 (7)
C46	0.6698 (5)	0.21963 (12)	0.0566 (2)	0.0607 (8)
H46	0.7872	0.2447	0.0711	0.073*
C47	0.6789 (6)	0.19115 (13)	−0.0227 (2)	0.0671 (8)
H47	0.8014	0.1963	−0.0610	0.081*
C48	0.5029 (7)	0.15541 (13)	−0.0426 (2)	0.0689 (9)
C49	0.3243 (7)	0.14560 (14)	0.0122 (3)	0.0758 (10)
H49	0.2083	0.1204	−0.0031	0.091*
C50	0.3179 (6)	0.17378 (13)	0.0911 (3)	0.0696 (9)
H50	0.1964	0.1674	0.1294	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0668 (5)	0.0716 (5)	0.0607 (5)	−0.0069 (4)	0.0122 (4)	−0.0014 (4)
S2	0.0692 (5)	0.0773 (5)	0.0529 (5)	0.0069 (4)	−0.0124 (4)	−0.0081 (4)
F1	0.177 (2)	0.0779 (13)	0.0908 (16)	−0.0016 (15)	0.0292 (17)	−0.0204 (13)
F2	0.1388 (19)	0.0879 (13)	0.0854 (15)	−0.0013 (14)	−0.0106 (15)	−0.0298 (13)
N1	0.0642 (15)	0.0663 (15)	0.0432 (14)	−0.0055 (13)	0.0048 (12)	0.0038 (12)
N2	0.0670 (16)	0.0699 (16)	0.0547 (16)	0.0006 (13)	0.0104 (13)	0.0083 (13)
N3	0.0647 (16)	0.0700 (17)	0.0518 (16)	0.0040 (13)	0.0053 (13)	0.0062 (13)
N4	0.0555 (14)	0.0685 (16)	0.0512 (15)	0.0116 (12)	−0.0105 (12)	0.0020 (13)
N5	0.0650 (15)	0.0591 (15)	0.0655 (17)	0.0098 (12)	−0.0209 (13)	−0.0019 (13)
N6	0.0581 (14)	0.0603 (14)	0.0582 (16)	0.0021 (12)	−0.0104 (13)	−0.0035 (12)
C1	0.0609 (18)	0.0634 (18)	0.0467 (17)	−0.0098 (15)	−0.0093 (14)	−0.0040 (14)
C2	0.072 (2)	0.083 (2)	0.067 (2)	−0.0057 (19)	0.0038 (18)	0.0146 (18)
C3	0.086 (3)	0.077 (2)	0.084 (3)	0.007 (2)	0.001 (2)	0.021 (2)
C4	0.095 (3)	0.075 (2)	0.080 (3)	0.012 (2)	−0.013 (2)	0.003 (2)
C5	0.065 (2)	0.097 (3)	0.065 (2)	−0.001 (2)	0.0001 (17)	−0.010 (2)
C6	0.067 (2)	0.074 (2)	0.0554 (19)	−0.0061 (17)	0.0055 (16)	−0.0052 (16)
C7	0.0610 (18)	0.0633 (18)	0.0418 (16)	−0.0145 (15)	−0.0016 (14)	−0.0017 (14)
C8	0.071 (2)	0.0666 (18)	0.0557 (19)	−0.0123 (16)	0.0138 (17)	0.0013 (16)
C9	0.0605 (17)	0.0673 (18)	0.0400 (16)	−0.0059 (15)	−0.0001 (14)	0.0010 (14)
C10	0.0497 (16)	0.077 (2)	0.0553 (19)	−0.0016 (15)	−0.0042 (15)	0.0081 (16)
C11	0.066 (2)	0.070 (2)	0.063 (2)	−0.0097 (16)	0.0016 (17)	0.0006 (16)
C12	0.0578 (17)	0.0697 (19)	0.0431 (16)	−0.0068 (15)	−0.0077 (14)	0.0023 (15)
C13	0.0549 (17)	0.0694 (19)	0.0454 (17)	−0.0034 (15)	−0.0060 (14)	−0.0019 (15)
C14	0.067 (2)	0.070 (2)	0.0549 (19)	−0.0090 (16)	−0.0011 (16)	0.0005 (15)
C15	0.0645 (19)	0.083 (2)	0.0536 (19)	−0.0008 (18)	0.0027 (16)	−0.0129 (18)
C16	0.066 (2)	0.070 (2)	0.0495 (18)	−0.0079 (16)	−0.0076 (16)	−0.0106 (16)
C17	0.072 (2)	0.0660 (19)	0.060 (2)	−0.0098 (17)	−0.0073 (17)	0.0031 (16)
C18	0.0619 (18)	0.078 (2)	0.055 (2)	−0.0063 (17)	0.0025 (15)	0.0022 (17)
C19	0.093 (3)	0.076 (2)	0.079 (3)	0.002 (2)	−0.003 (2)	−0.018 (2)
C20	0.0501 (16)	0.0601 (16)	0.0524 (18)	−0.0029 (14)	0.0026 (14)	0.0095 (14)
C21	0.0591 (18)	0.0691 (19)	0.063 (2)	0.0061 (15)	−0.0053 (16)	0.0031 (16)
C22	0.086 (2)	0.074 (2)	0.061 (2)	−0.0015 (19)	−0.0048 (19)	−0.0029 (18)
C23	0.101 (3)	0.0535 (18)	0.065 (2)	−0.0041 (19)	0.018 (2)	−0.0044 (17)
C24	0.079 (2)	0.072 (2)	0.094 (3)	0.0243 (19)	0.025 (2)	0.012 (2)
C25	0.064 (2)	0.076 (2)	0.072 (2)	0.0103 (17)	0.0082 (18)	0.0179 (19)
C26	0.0527 (17)	0.0735 (19)	0.0421 (16)	0.0104 (15)	−0.0006 (13)	0.0056 (14)
C27	0.0572 (18)	0.086 (2)	0.065 (2)	0.0125 (16)	−0.0054 (16)	0.0035 (17)
C28	0.072 (2)	0.090 (3)	0.070 (2)	0.032 (2)	−0.0053 (18)	0.011 (2)
C29	0.089 (2)	0.075 (2)	0.057 (2)	0.021 (2)	−0.0019 (19)	0.0079 (18)
C30	0.082 (2)	0.074 (2)	0.063 (2)	0.0094 (18)	−0.0098 (18)	0.0033 (17)
C31	0.0614 (18)	0.075 (2)	0.056 (2)	0.0131 (17)	−0.0110 (15)	0.0077 (16)
C32	0.0491 (16)	0.0733 (19)	0.0427 (16)	0.0079 (14)	−0.0031 (13)	0.0041 (15)
C33	0.0628 (18)	0.084 (2)	0.0461 (18)	0.0082 (16)	−0.0112 (15)	0.0038 (16)
C34	0.0531 (16)	0.0656 (18)	0.0464 (17)	0.0087 (15)	−0.0025 (13)	−0.0003 (15)
C35	0.0519 (16)	0.0605 (17)	0.0549 (18)	−0.0004 (13)	−0.0085 (14)	0.0037 (14)
C36	0.0619 (18)	0.0592 (18)	0.064 (2)	0.0058 (15)	−0.0104 (16)	0.0040 (15)
C37	0.0552 (17)	0.0613 (17)	0.0465 (17)	0.0025 (14)	−0.0024 (14)	0.0037 (14)
C38	0.0543 (16)	0.0603 (17)	0.0447 (16)	−0.0033 (14)	0.0028 (13)	0.0045 (14)
C39	0.0578 (18)	0.0704 (19)	0.0540 (18)	−0.0023 (15)	−0.0047 (15)	0.0073 (16)
C40	0.074 (2)	0.067 (2)	0.061 (2)	−0.0159 (17)	−0.0003 (18)	−0.0023 (17)
C41	0.073 (2)	0.0603 (18)	0.0528 (18)	−0.0029 (16)	0.0070 (16)	0.0015 (15)
C42	0.0629 (19)	0.0662 (19)	0.065 (2)	0.0081 (16)	−0.0029 (16)	0.0008 (17)
C43	0.0617 (18)	0.0603 (18)	0.066 (2)	0.0000 (15)	−0.0092 (16)	−0.0009 (16)
C44	0.116 (3)	0.062 (2)	0.092 (3)	0.003 (2)	−0.004 (2)	−0.004 (2)
C45	0.0508 (16)	0.0504 (15)	0.0544 (18)	−0.0006 (13)	−0.0078 (15)	0.0096 (13)
C46	0.0610 (18)	0.0540 (16)	0.067 (2)	−0.0112 (14)	−0.0064 (17)	0.0056 (16)
C47	0.072 (2)	0.0654 (18)	0.064 (2)	−0.0014 (17)	0.0083 (17)	0.0076 (17)
C48	0.086 (2)	0.0556 (18)	0.065 (2)	0.0055 (17)	−0.012 (2)	−0.0073 (16)
C49	0.078 (2)	0.068 (2)	0.081 (3)	−0.0147 (18)	−0.013 (2)	−0.0119 (19)
C50	0.0591 (18)	0.0695 (19)	0.080 (2)	−0.0128 (16)	−0.0003 (17)	0.0046 (19)

Geometric parameters (Å, º) top

S1—C8	1.719 (3)	C20—C25	1.379 (4)
S1—C9	1.724 (3)	C21—C22	1.384 (5)
S2—C33	1.719 (3)	C21—H21	0.9300
S2—C34	1.723 (3)	C22—C23	1.337 (5)
F1—C23	1.371 (4)	C22—H22	0.9300
F2—C48	1.369 (4)	C23—C24	1.353 (5)
N1—C9	1.297 (4)	C24—C25	1.381 (5)
N1—C7	1.393 (4)	C24—H24	0.9300
N2—C9	1.386 (4)	C25—H25	0.9300
N2—N3	1.393 (4)	C26—C31	1.379 (4)
N2—C10	1.479 (4)	C26—C27	1.400 (4)
N3—C12	1.288 (4)	C26—C32	1.483 (4)
N4—C34	1.294 (4)	C27—C28	1.373 (5)
N4—C32	1.396 (3)	C27—H27	0.9300
N5—C34	1.384 (3)	C28—C29	1.370 (5)
N5—N6	1.396 (3)	C28—H28	0.9300
N5—C35	1.489 (3)	C29—C30	1.379 (5)
N6—C37	1.286 (3)	C29—H29	0.9300
C1—C6	1.381 (4)	C30—C31	1.377 (5)
C1—C2	1.399 (4)	C30—H30	0.9300
C1—C7	1.476 (4)	C31—H31	0.9300
C2—C3	1.379 (5)	C32—C33	1.349 (4)
C2—H2A	0.9300	C33—H33	0.9300
C3—C4	1.364 (5)	C35—C45	1.500 (4)
C3—H3	0.9300	C35—C36	1.537 (4)
C4—C5	1.377 (5)	C35—H35	0.9800
C4—H4	0.9300	C36—C37	1.498 (4)
C5—C6	1.384 (5)	C36—H36A	0.9700
C5—H5	0.9300	C36—H36B	0.9700
C6—H6	0.9300	C37—C38	1.461 (4)
C7—C8	1.347 (4)	C38—C43	1.385 (4)
C8—H8	0.9300	C38—C39	1.392 (4)
C10—C20	1.502 (4)	C39—C40	1.388 (4)
C10—C11	1.541 (4)	C39—H39	0.9300
C10—H10	0.9800	C40—C41	1.384 (4)
C11—C12	1.498 (5)	C40—H40	0.9300
C11—H11A	0.9700	C41—C42	1.366 (4)
C11—H11B	0.9700	C41—C44	1.518 (4)
C12—C13	1.472 (4)	C42—C43	1.384 (4)
C13—C14	1.384 (4)	C42—H42	0.9300
C13—C18	1.388 (4)	C43—H43	0.9300
C14—C15	1.371 (4)	C44—H44A	0.9600
C14—H14	0.9300	C44—H44B	0.9600
C15—C16	1.400 (5)	C44—H44C	0.9600
C15—H15	0.9300	C45—C46	1.372 (4)
C16—C17	1.370 (4)	C45—C50	1.395 (4)
C16—C19	1.498 (5)	C46—C47	1.388 (5)
C17—C18	1.390 (5)	C46—H46	0.9300
C17—H17	0.9300	C47—C48	1.360 (5)
C18—H18	0.9300	C47—H47	0.9300
C19—H19A	0.9600	C48—C49	1.354 (5)
C19—H19B	0.9600	C49—C50	1.378 (5)
C19—H19C	0.9600	C49—H49	0.9300
C20—C21	1.379 (4)	C50—H50	0.9300

C8—S1—C9	87.38 (16)	C23—C24—C25	119.7 (3)
C33—S2—C34	87.58 (14)	C23—C24—H24	120.2
C9—N1—C7	108.8 (3)	C25—C24—H24	120.2
C9—N2—N3	116.0 (3)	C20—C25—C24	120.2 (3)
C9—N2—C10	123.0 (2)	C20—C25—H25	119.9
N3—N2—C10	113.1 (2)	C24—C25—H25	119.9
C12—N3—N2	108.2 (3)	C31—C26—C27	118.0 (3)
C34—N4—C32	109.2 (2)	C31—C26—C32	121.1 (2)
C34—N5—N6	115.1 (2)	C27—C26—C32	120.9 (3)
C34—N5—C35	123.0 (2)	C28—C27—C26	120.7 (3)
N6—N5—C35	112.4 (2)	C28—C27—H27	119.7
C37—N6—N5	108.6 (2)	C26—C27—H27	119.7
C6—C1—C2	117.9 (3)	C29—C28—C27	120.5 (3)
C6—C1—C7	121.5 (3)	C29—C28—H28	119.7
C2—C1—C7	120.6 (3)	C27—C28—H28	119.7
C3—C2—C1	120.7 (4)	C28—C29—C30	119.5 (3)
C3—C2—H2A	119.6	C28—C29—H29	120.2
C1—C2—H2A	119.6	C30—C29—H29	120.2
C4—C3—C2	120.7 (4)	C31—C30—C29	120.3 (3)
C4—C3—H3	119.6	C31—C30—H30	119.9
C2—C3—H3	119.6	C29—C30—H30	119.9
C3—C4—C5	119.4 (4)	C30—C31—C26	121.0 (3)
C3—C4—H4	120.3	C30—C31—H31	119.5
C5—C4—H4	120.3	C26—C31—H31	119.5
C4—C5—C6	120.5 (4)	C33—C32—N4	114.5 (3)
C4—C5—H5	119.7	C33—C32—C26	126.2 (2)
C6—C5—H5	119.7	N4—C32—C26	119.3 (3)
C5—C6—C1	120.8 (3)	C32—C33—S2	111.6 (2)
C5—C6—H6	119.6	C32—C33—H33	124.2
C1—C6—H6	119.6	S2—C33—H33	124.2
C8—C7—N1	114.9 (3)	N4—C34—N5	122.8 (3)
C8—C7—C1	126.6 (3)	N4—C34—S2	117.1 (2)
N1—C7—C1	118.5 (3)	N5—C34—S2	120.0 (2)
C7—C8—S1	111.6 (2)	N5—C35—C45	113.6 (3)
C7—C8—H8	124.2	N5—C35—C36	100.2 (2)
S1—C8—H8	124.2	C45—C35—C36	113.2 (2)
N1—C9—N2	122.6 (3)	N5—C35—H35	109.8
N1—C9—S1	117.3 (2)	C45—C35—H35	109.8
N2—C9—S1	120.1 (2)	C36—C35—H35	109.8
N2—C10—C20	111.9 (2)	C37—C36—C35	104.0 (2)
N2—C10—C11	100.6 (2)	C37—C36—H36A	111.0
C20—C10—C11	115.1 (3)	C35—C36—H36A	111.0
N2—C10—H10	109.6	C37—C36—H36B	111.0
C20—C10—H10	109.6	C35—C36—H36B	111.0
C11—C10—H10	109.6	H36A—C36—H36B	109.0
C12—C11—C10	103.4 (3)	N6—C37—C38	122.2 (3)
C12—C11—H11A	111.1	N6—C37—C36	113.1 (3)
C10—C11—H11A	111.1	C38—C37—C36	124.7 (2)
C12—C11—H11B	111.1	C43—C38—C39	117.4 (3)
C10—C11—H11B	111.1	C43—C38—C37	121.0 (3)
H11A—C11—H11B	109.0	C39—C38—C37	121.6 (3)
N3—C12—C13	120.1 (3)	C40—C39—C38	120.5 (3)
N3—C12—C11	113.6 (3)	C40—C39—H39	119.7
C13—C12—C11	126.2 (3)	C38—C39—H39	119.7
C14—C13—C18	117.8 (3)	C41—C40—C39	121.4 (3)
C14—C13—C12	121.3 (3)	C41—C40—H40	119.3
C18—C13—C12	120.8 (3)	C39—C40—H40	119.3
C15—C14—C13	121.1 (3)	C42—C41—C40	118.1 (3)
C15—C14—H14	119.5	C42—C41—C44	120.7 (3)
C13—C14—H14	119.5	C40—C41—C44	121.2 (3)
C14—C15—C16	121.8 (3)	C41—C42—C43	121.1 (3)
C14—C15—H15	119.1	C41—C42—H42	119.4
C16—C15—H15	119.1	C43—C42—H42	119.4
C17—C16—C15	116.7 (3)	C38—C43—C42	121.5 (3)
C17—C16—C19	122.9 (3)	C38—C43—H43	119.2
C15—C16—C19	120.4 (3)	C42—C43—H43	119.2
C16—C17—C18	122.2 (3)	C41—C44—H44A	109.5
C16—C17—H17	118.9	C41—C44—H44B	109.5
C18—C17—H17	118.9	H44A—C44—H44B	109.5
C17—C18—C13	120.4 (3)	C41—C44—H44C	109.5
C17—C18—H18	119.8	H44A—C44—H44C	109.5
C13—C18—H18	119.8	H44B—C44—H44C	109.5
C16—C19—H19A	109.5	C46—C45—C50	118.2 (3)
C16—C19—H19B	109.5	C46—C45—C35	122.8 (3)
H19A—C19—H19B	109.5	C50—C45—C35	118.8 (3)
C16—C19—H19C	109.5	C45—C46—C47	121.5 (3)
H19A—C19—H19C	109.5	C45—C46—H46	119.3
H19B—C19—H19C	109.5	C47—C46—H46	119.3
C21—C20—C25	117.7 (3)	C48—C47—C46	117.9 (3)
C21—C20—C10	120.2 (3)	C48—C47—H47	121.1
C25—C20—C10	122.1 (3)	C46—C47—H47	121.1
C20—C21—C22	122.0 (3)	C49—C48—C47	123.0 (3)
C20—C21—H21	119.0	C49—C48—F2	118.7 (3)
C22—C21—H21	119.0	C47—C48—F2	118.3 (4)
C23—C22—C21	118.0 (3)	C48—C49—C50	118.6 (3)
C23—C22—H22	121.0	C48—C49—H49	120.7
C21—C22—H22	121.0	C50—C49—H49	120.7
C22—C23—C24	122.4 (3)	C49—C50—C45	120.8 (4)
C22—C23—F1	119.0 (4)	C49—C50—H50	119.6
C24—C23—F1	118.6 (4)	C45—C50—H50	119.6

C9—N2—N3—C12	−157.5 (2)	C10—C20—C25—C24	178.5 (3)
C10—N2—N3—C12	−7.5 (3)	C23—C24—C25—C20	1.6 (5)
C34—N5—N6—C37	−157.5 (3)	C31—C26—C27—C28	−0.2 (5)
C35—N5—N6—C37	−10.0 (3)	C32—C26—C27—C28	177.8 (3)
C6—C1—C2—C3	0.8 (5)	C26—C27—C28—C29	0.2 (5)
C7—C1—C2—C3	−177.7 (3)	C27—C28—C29—C30	−0.6 (6)
C1—C2—C3—C4	−2.0 (5)	C28—C29—C30—C31	1.0 (5)
C2—C3—C4—C5	1.8 (6)	C29—C30—C31—C26	−1.0 (5)
C3—C4—C5—C6	−0.5 (5)	C27—C26—C31—C30	0.5 (5)
C4—C5—C6—C1	−0.7 (5)	C32—C26—C31—C30	−177.4 (3)
C2—C1—C6—C5	0.5 (4)	C34—N4—C32—C33	1.2 (4)
C7—C1—C6—C5	179.0 (3)	C34—N4—C32—C26	−180.0 (3)
C9—N1—C7—C8	0.6 (3)	C31—C26—C32—C33	157.8 (3)
C9—N1—C7—C1	−178.6 (2)	C27—C26—C32—C33	−20.1 (5)
C6—C1—C7—C8	171.7 (3)	C31—C26—C32—N4	−20.9 (4)
C2—C1—C7—C8	−9.8 (4)	C27—C26—C32—N4	161.2 (3)
C6—C1—C7—N1	−9.2 (4)	N4—C32—C33—S2	−0.4 (4)
C2—C1—C7—N1	169.3 (3)	C26—C32—C33—S2	−179.1 (3)
N1—C7—C8—S1	−0.3 (3)	C34—S2—C33—C32	−0.3 (3)
C1—C7—C8—S1	178.8 (2)	C32—N4—C34—N5	175.9 (3)
C9—S1—C8—C7	0.0 (2)	C32—N4—C34—S2	−1.5 (4)
C7—N1—C9—N2	178.3 (2)	N6—N5—C34—N4	171.7 (3)
C7—N1—C9—S1	−0.7 (3)	C35—N5—C34—N4	28.0 (5)
N3—N2—C9—N1	166.1 (3)	N6—N5—C34—S2	−10.9 (4)
C10—N2—C9—N1	19.3 (4)	C35—N5—C34—S2	−154.7 (2)
N3—N2—C9—S1	−15.0 (3)	C33—S2—C34—N4	1.1 (3)
C10—N2—C9—S1	−161.7 (2)	C33—S2—C34—N5	−176.4 (3)
C8—S1—C9—N1	0.4 (2)	C34—N5—C35—C45	−81.5 (4)
C8—S1—C9—N2	−178.6 (2)	N6—N5—C35—C45	133.9 (3)
C9—N2—C10—C20	−78.9 (3)	C34—N5—C35—C36	157.5 (3)
N3—N2—C10—C20	133.5 (2)	N6—N5—C35—C36	12.9 (3)
C9—N2—C10—C11	158.3 (3)	N5—C35—C36—C37	−10.7 (3)
N3—N2—C10—C11	10.7 (3)	C45—C35—C36—C37	−132.0 (3)
N2—C10—C11—C12	−9.4 (3)	N5—N6—C37—C38	−177.7 (3)
C20—C10—C11—C12	−129.9 (3)	N5—N6—C37—C36	1.9 (4)
N2—N3—C12—C13	−177.4 (2)	C35—C36—C37—N6	6.2 (4)
N2—N3—C12—C11	0.4 (3)	C35—C36—C37—C38	−174.2 (3)
C10—C11—C12—N3	6.2 (3)	N6—C37—C38—C43	−177.0 (3)
C10—C11—C12—C13	−176.1 (3)	C36—C37—C38—C43	3.4 (5)
N3—C12—C13—C14	−0.7 (4)	N6—C37—C38—C39	3.1 (5)
C11—C12—C13—C14	−178.2 (3)	C36—C37—C38—C39	−176.5 (3)
N3—C12—C13—C18	178.6 (3)	C43—C38—C39—C40	0.2 (5)
C11—C12—C13—C18	1.1 (4)	C37—C38—C39—C40	−179.9 (3)
C18—C13—C14—C15	−2.6 (4)	C38—C39—C40—C41	−0.3 (5)
C12—C13—C14—C15	176.7 (3)	C39—C40—C41—C42	−0.1 (5)
C13—C14—C15—C16	0.6 (4)	C39—C40—C41—C44	−178.4 (3)
C14—C15—C16—C17	1.5 (4)	C40—C41—C42—C43	0.6 (5)
C14—C15—C16—C19	−176.8 (3)	C44—C41—C42—C43	179.0 (3)
C15—C16—C17—C18	−1.7 (4)	C39—C38—C43—C42	0.4 (5)
C19—C16—C17—C18	176.6 (3)	C37—C38—C43—C42	−179.6 (3)
C16—C17—C18—C13	−0.3 (4)	C41—C42—C43—C38	−0.8 (5)
C14—C13—C18—C17	2.4 (4)	N5—C35—C45—C46	−32.9 (4)
C12—C13—C18—C17	−176.9 (3)	C36—C35—C45—C46	80.5 (3)
N2—C10—C20—C21	−58.9 (4)	N5—C35—C45—C50	152.4 (3)
C11—C10—C20—C21	55.1 (4)	C36—C35—C45—C50	−94.2 (3)
N2—C10—C20—C25	120.4 (3)	C50—C45—C46—C47	0.3 (4)
C11—C10—C20—C25	−125.6 (3)	C35—C45—C46—C47	−174.5 (3)
C25—C20—C21—C22	1.7 (5)	C45—C46—C47—C48	0.9 (5)
C10—C20—C21—C22	−179.1 (3)	C46—C47—C48—C49	−1.7 (5)
C20—C21—C22—C23	−0.5 (5)	C46—C47—C48—F2	179.4 (3)
C21—C22—C23—C24	−0.2 (6)	C47—C48—C49—C50	1.2 (5)
C21—C22—C23—F1	178.0 (3)	F2—C48—C49—C50	−179.9 (3)
C22—C23—C24—C25	−0.4 (6)	C48—C49—C50—C45	0.1 (5)
F1—C23—C24—C25	−178.6 (3)	C46—C45—C50—C49	−0.8 (4)
C21—C20—C25—C24	−2.2 (5)	C35—C45—C50—C49	174.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C26–C31, C45–C50, S2,N4,C32–C34 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Cg1	0.93	2.75	3.537 (3)	143
C19—H19A···Cg2ⁱ	0.96	2.94	3.596 (4)	127
C35—H35···Cg3ⁱⁱ	0.98	2.94	3.843 (3)	153
C42—H42···Cg4ⁱⁱⁱ	0.93	2.86	3.567 (3)	134

Symmetry codes: (i) x, −y, z+1/2; (ii) x−1, y, z; (iii) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₀FN₃S
M_r	413.50
Crystal system, space group	Monoclinic, Pc
Temperature (K)	295
a, b, c (Å)	5.7563 (3), 24.1214 (12), 15.1827 (8)
β (°)	90.948 (5)
V (Å³)	2107.83 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.837, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	22651, 9054, 5841
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.117, 0.99
No. of reflections	9054
No. of parameters	543
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.16
Absolute structure	Flack (1983), 4165 Friedel pairs
Absolute structure parameter	−0.06 (6)

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C26–C31, C45–C50, S2,N4,C32–C34 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Cg1	0.93	2.75	3.537 (3)	143
C19—H19A···Cg2ⁱ	0.96	2.94	3.596 (4)	127
C35—H35···Cg3ⁱⁱ	0.98	2.94	3.843 (3)	153
C42—H42···Cg4ⁱⁱⁱ	0.93	2.86	3.567 (3)	134

Symmetry codes: (i) x, −y, z+1/2; (ii) x−1, y, z; (iii) x, −y+1, z−1/2.

Footnotes

‡Additional correspondence author, e-mail: bakrfatehy@yahoo.com.

Acknowledgements

We thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Abdel-Wahab, B. F., Abdel-Aziz, H. A. & Ahmed, E. M. (2009). Eur. J. Med. Chem. 44, 2632–2635. Web of Science PubMed CAS Google Scholar
Abdel-Wahab, B. F., Abdel-Latif, E., Mohamed, H. A. & Awad, G. E. A. (2012). Eur. J. Med. Chem. 52, 263–268. Web of Science CAS PubMed Google Scholar
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Chimenti, F., Carradori, S., Secci, D., Bolasco, A., Bizzarri, B., Chimenti, P., Granese, A., Yáñez, M. & Orallo, F. (2010). Eur. J. Med. Chem. 45, 800–804. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 69| Part 3| March 2013| Pages o392-o393

doi:10.1107/S1600536813004339

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

2-[5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-di­hydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

2-[5-(4-Fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thiazole