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

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

doi:10.1107/S1600536813008179

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o618

doi:10.1107/S1600536813008179

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

Bakr F. Abdel-Wahab,^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 25 March 2013; accepted 25 March 2013; online 28 March 2013)

In the title compound, C₂₈H₂₃FN₆S, the pyrazole ring adopts an envelope conformation, with the methine C atom being the flap atom. With respect to this ring, the 2-thienyl, triazole and fluorobenzene rings are approximately coplanar, coplanar and perpendicular, respectively [dihedral angles = 8.56 (17), 6.03 (19) and 73.1 (2)°, respectively] so that to a first approximation the molecule has a T-shape. In the crystal, molecules are consolidated into a three-dimensional architecture by C—H⋯F (involving a bifurcated F atom), C—H⋯S and C—H⋯π interactions.

Related literature

For the synthesis, structure and biological activity of 1-thiazol-2-ylpyrazoline, see: Abdel-Wahab et al. (2012 ); Dong et al. (2011 ).

Experimental

Crystal data

C₂₈H₂₃FN₆S
M_r = 494.58
Monoclinic, P 2₁ /n
a = 17.7373 (18) Å
b = 7.8367 (7) Å
c = 19.4159 (18) Å
β = 109.323 (11)°
V = 2546.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.16 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 = 0.901, T_max = 1.000
16284 measured reflections
5871 independent reflections
2694 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.232
S = 1.06
5871 reflections
328 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C22–C27 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯S1ⁱ	0.93	2.87	3.743 (4)	156
C24—H24⋯F1ⁱⁱ	0.93	2.55	3.476 (5)	177
C28—H28B⋯F1ⁱⁱⁱ	0.96	2.53	3.308 (5)	138
C27—H27⋯Cg1ⁱ	0.93	2.75	3.518 (4)	141
C14—H14⋯Cg2ⁱⁱ	0.93	2.85	3.756 (5)	164
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x-1, y, z.

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 ) 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/S1600536813008179/su2580sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813008179/su2580Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813008179/su2580Isup3.cml

checkCIF report

Comment top

The title compound, (I), was characterized in relation to on-going studies into the synthesis, structure and biological activities of 1-thiazol-2-ylpyrazoline derivatives (Abdel-Wahab et al., 2012; Dong et al., 2011).

In (I), the pyrazolyl ring adopts an envelope conformation with the methine-C10 atom being the flap atom. The 2-thienyl and triazole rings are approximately co-planar with the central five-membered ring forming dihedral angles of 8.56 (17) and 6.03 (19)°, respectively; the dihedral angle between these rings is 14.33 (17)°, indicating an overall twist in the molecule. By contrast, the fluorobenzene ring is almost perpendicular to the pyrazolyl ring, forming a dihedral angle of 73.1 (2)°. With respect to the respective attached five-membered ring, the phenyl and p-tolyl residues form dihedral angles of 2.88 (17) and 45.58 (18)°, respectively, indicating co-planar and inclined dispositions. Overall, the shape of the molecule resembles the distorted T-shape reported for the chlorobenzene derivative (Dong et al., 2011).

The three-dimensional architecture is consolidated by C—H···F, involving a bifurcated F1 atom, C—H···S and C—H···π interactions, Fig. 2 and Table 1.

Related literature top

For the synthesis, structure and biological activity of 1-thiazol-2-ylpyrazoline, see: Abdel-Wahab et al. (2012); Dong et al. (2011).

Experimental top

The title compound was prepared according to the reported method (Abdel-Wahab et al., 2012). Beige crystals were obtained from its DMF solution by slow evaporation at room temperature.

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) 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. A view of the crystal packing in projection down the a axis. The C—H···F, C—H···S and C—H···π interactions are shown as blue, orange and purple dashed lines, respectively.

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

Crystal data top

C₂₈H₂₃FN₆S	F(000) = 1032
M_r = 494.58	D_x = 1.290 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2615 reflections
a = 17.7373 (18) Å	θ = 2.9–27.5°
b = 7.8367 (7) Å	µ = 0.16 mm⁻¹
c = 19.4159 (18) Å	T = 295 K
β = 109.323 (11)°	Prism, light-brown
V = 2546.8 (4) Å³	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5871 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2694 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.038
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.9°
ω scan	h = −23→23
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→7
T_min = 0.901, T_max = 1.000	l = −25→25
16284 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)] = 0.065	H-atom parameters constrained
wR(F²) = 0.232	w = 1/[σ²(F_o²) + (0.0967P)² + 0.2203P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
5871 reflections	Δρ_max = 0.35 e Å⁻³
328 parameters	Δρ_min = −0.38 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (12)

Crystal data top

C₂₈H₂₃FN₆S	V = 2546.8 (4) Å³
M_r = 494.58	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 17.7373 (18) Å	µ = 0.16 mm⁻¹
b = 7.8367 (7) Å	T = 295 K
c = 19.4159 (18) Å	0.40 × 0.30 × 0.20 mm
β = 109.323 (11)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5871 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2694 reflections with I > 2σ(I)
T_min = 0.901, T_max = 1.000	R_int = 0.038
16284 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.232	H-atom parameters constrained
S = 1.06	Δρ_max = 0.35 e Å⁻³
5871 reflections	Δρ_min = −0.38 e Å⁻³
328 parameters

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	0.53552 (5)	0.20817 (11)	0.54592 (4)	0.0861 (3)
F1	0.71777 (15)	0.6920 (6)	0.2659 (2)	0.248 (2)
N1	0.61200 (15)	0.1843 (3)	0.45456 (13)	0.0749 (7)
N2	0.48605 (15)	0.3127 (4)	0.40552 (13)	0.0869 (8)
N3	0.41199 (15)	0.3365 (3)	0.41211 (14)	0.0795 (7)
N4	0.22891 (18)	0.4311 (4)	0.26442 (14)	0.1003 (9)
N5	0.15671 (17)	0.4606 (4)	0.26545 (14)	0.1023 (9)
N6	0.16075 (15)	0.4627 (3)	0.33692 (13)	0.0823 (7)
C1	0.7421 (2)	0.0649 (4)	0.52615 (17)	0.0782 (8)
C2	0.7666 (2)	0.0676 (5)	0.4651 (2)	0.0999 (11)
H2	0.7319	0.1057	0.4205	0.120*
C3	0.8434 (3)	0.0133 (6)	0.4707 (3)	0.1212 (14)
H3	0.8594	0.0144	0.4297	0.145*
C4	0.8952 (3)	−0.0417 (6)	0.5361 (3)	0.1240 (15)
H4	0.9462	−0.0786	0.5398	0.149*
C5	0.8711 (3)	−0.0418 (5)	0.5959 (2)	0.1078 (12)
H5	0.9065	−0.0773	0.6407	0.129*
C6	0.7966 (2)	0.0089 (4)	0.59155 (19)	0.0888 (9)
H6	0.7816	0.0061	0.6332	0.107*
C7	0.66171 (18)	0.1232 (4)	0.52085 (16)	0.0718 (8)
C8	0.6299 (2)	0.1261 (4)	0.57531 (16)	0.0853 (9)
H8	0.6561	0.0883	0.6226	0.102*
C9	0.54482 (19)	0.2344 (4)	0.46099 (16)	0.0738 (8)
C10	0.48409 (18)	0.3077 (4)	0.32859 (16)	0.0821 (9)
H10	0.4875	0.1889	0.3141	0.099*
C11	0.39996 (18)	0.3751 (5)	0.28987 (17)	0.0931 (10)
H11A	0.4015	0.4900	0.2718	0.112*
H11B	0.3712	0.3018	0.2494	0.112*
C12	0.36238 (19)	0.3725 (4)	0.34853 (16)	0.0772 (8)
C13	0.54996 (17)	0.4088 (4)	0.31593 (15)	0.0739 (8)
C14	0.5802 (3)	0.3588 (6)	0.2630 (2)	0.1267 (15)
H14	0.5626	0.2574	0.2379	0.152*
C15	0.6349 (4)	0.4536 (11)	0.2466 (4)	0.169 (3)
H15	0.6530	0.4188	0.2090	0.203*
C16	0.6632 (3)	0.5932 (11)	0.2821 (4)	0.153 (3)
C17	0.6367 (3)	0.6507 (7)	0.3366 (3)	0.1339 (17)
H17	0.6568	0.7507	0.3618	0.161*
C18	0.5788 (2)	0.5554 (5)	0.35322 (19)	0.0985 (11)
H18	0.5597	0.5918	0.3899	0.118*
C19	0.27929 (18)	0.4113 (4)	0.33473 (17)	0.0775 (8)
C20	0.23657 (17)	0.4322 (4)	0.38183 (16)	0.0736 (8)
C21	0.26213 (18)	0.4199 (4)	0.46230 (16)	0.0849 (9)
H21A	0.3071	0.3444	0.4793	0.127*
H21B	0.2189	0.3762	0.4766	0.127*
H21C	0.2769	0.5310	0.4832	0.127*
C22	0.08855 (17)	0.4876 (4)	0.35273 (16)	0.0770 (8)
C23	0.0206 (2)	0.4008 (5)	0.31273 (19)	0.0984 (11)
H23	0.0212	0.3283	0.2750	0.118*
C24	−0.0483 (2)	0.4236 (5)	0.3297 (2)	0.1067 (12)
H24	−0.0941	0.3647	0.3027	0.128*
C25	−0.0523 (2)	0.5298 (5)	0.3849 (2)	0.0941 (10)
C26	0.0160 (2)	0.6152 (5)	0.42197 (19)	0.0967 (10)
H26	0.0154	0.6892	0.4592	0.116*
C27	0.08582 (19)	0.5965 (4)	0.40657 (17)	0.0853 (9)
H27	0.1310	0.6581	0.4328	0.102*
C28	−0.1285 (2)	0.5489 (7)	0.4025 (2)	0.1334 (16)
H28A	−0.1597	0.4466	0.3889	0.200*
H28B	−0.1585	0.6439	0.3759	0.200*
H28C	−0.1159	0.5683	0.4539	0.200*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.1046 (7)	0.0881 (7)	0.0660 (5)	0.0002 (4)	0.0289 (5)	0.0001 (4)
F1	0.0915 (17)	0.367 (6)	0.276 (4)	0.002 (2)	0.048 (2)	0.218 (4)
N1	0.0815 (16)	0.0787 (17)	0.0566 (14)	−0.0108 (13)	0.0121 (12)	0.0048 (12)
N2	0.0781 (17)	0.118 (2)	0.0608 (15)	−0.0031 (15)	0.0186 (13)	0.0145 (15)
N3	0.0771 (16)	0.0888 (19)	0.0721 (17)	−0.0051 (13)	0.0240 (14)	0.0077 (14)
N4	0.103 (2)	0.128 (3)	0.0606 (17)	0.0176 (18)	0.0145 (15)	−0.0013 (16)
N5	0.090 (2)	0.139 (3)	0.0665 (18)	0.0237 (18)	0.0114 (15)	0.0037 (17)
N6	0.0872 (18)	0.0913 (19)	0.0545 (14)	0.0063 (14)	0.0045 (13)	−0.0023 (13)
C1	0.099 (2)	0.0612 (18)	0.0675 (19)	−0.0033 (16)	0.0189 (18)	−0.0079 (15)
C2	0.110 (3)	0.103 (3)	0.080 (2)	0.010 (2)	0.023 (2)	−0.011 (2)
C3	0.124 (3)	0.138 (4)	0.109 (3)	0.015 (3)	0.049 (3)	−0.027 (3)
C4	0.107 (3)	0.113 (3)	0.145 (4)	0.024 (2)	0.032 (3)	−0.026 (3)
C5	0.116 (3)	0.088 (3)	0.103 (3)	0.014 (2)	0.014 (2)	−0.006 (2)
C6	0.093 (2)	0.080 (2)	0.085 (2)	0.0113 (18)	0.0173 (19)	0.0024 (18)
C7	0.087 (2)	0.0567 (17)	0.0628 (18)	−0.0061 (15)	0.0131 (15)	−0.0022 (14)
C8	0.110 (2)	0.085 (2)	0.0560 (17)	−0.0018 (18)	0.0210 (17)	0.0003 (16)
C9	0.0779 (19)	0.071 (2)	0.0670 (19)	−0.0120 (16)	0.0167 (16)	0.0023 (15)
C10	0.087 (2)	0.093 (2)	0.0625 (18)	−0.0042 (17)	0.0189 (16)	−0.0001 (17)
C11	0.078 (2)	0.125 (3)	0.068 (2)	−0.0075 (19)	0.0123 (16)	0.005 (2)
C12	0.086 (2)	0.080 (2)	0.0606 (18)	−0.0112 (17)	0.0175 (16)	−0.0003 (16)
C13	0.0767 (18)	0.093 (2)	0.0514 (16)	0.0136 (17)	0.0205 (14)	0.0038 (16)
C14	0.161 (4)	0.135 (4)	0.112 (3)	0.027 (3)	0.083 (3)	0.012 (3)
C15	0.143 (5)	0.243 (8)	0.164 (6)	0.060 (5)	0.107 (5)	0.070 (6)
C16	0.069 (2)	0.235 (8)	0.148 (5)	0.006 (4)	0.026 (3)	0.120 (6)
C17	0.118 (3)	0.150 (4)	0.107 (3)	−0.044 (3)	0.001 (3)	0.034 (3)
C18	0.105 (3)	0.113 (3)	0.079 (2)	−0.012 (2)	0.033 (2)	0.000 (2)
C19	0.0764 (19)	0.080 (2)	0.0680 (19)	−0.0005 (15)	0.0126 (16)	0.0001 (16)
C20	0.0786 (19)	0.0703 (19)	0.0626 (18)	−0.0070 (15)	0.0108 (16)	−0.0041 (15)
C21	0.0791 (19)	0.099 (2)	0.0642 (19)	−0.0076 (17)	0.0077 (15)	0.0022 (17)
C22	0.0748 (19)	0.078 (2)	0.0689 (19)	0.0059 (16)	0.0108 (15)	0.0019 (17)
C23	0.086 (2)	0.091 (3)	0.093 (2)	0.0097 (19)	−0.0051 (19)	−0.024 (2)
C24	0.067 (2)	0.099 (3)	0.126 (3)	0.0049 (18)	−0.006 (2)	−0.010 (2)
C25	0.078 (2)	0.104 (3)	0.088 (2)	0.0078 (19)	0.0110 (18)	0.013 (2)
C26	0.088 (2)	0.116 (3)	0.080 (2)	−0.001 (2)	0.0200 (19)	−0.010 (2)
C27	0.085 (2)	0.089 (2)	0.074 (2)	−0.0084 (17)	0.0150 (17)	−0.0117 (18)
C28	0.081 (2)	0.182 (5)	0.130 (3)	0.019 (3)	0.024 (2)	0.031 (3)

Geometric parameters (Å, º) top

S1—C8	1.706 (3)	C11—H11A	0.9700
S1—C9	1.723 (3)	C11—H11B	0.9700
F1—C16	1.355 (6)	C12—C19	1.441 (4)
N1—C9	1.299 (4)	C13—C18	1.364 (5)
N1—C7	1.383 (4)	C13—C14	1.365 (4)
N2—C9	1.371 (4)	C14—C15	1.341 (8)
N2—N3	1.374 (3)	C14—H14	0.9300
N2—C10	1.483 (4)	C15—C16	1.301 (9)
N3—C12	1.288 (4)	C15—H15	0.9300
N4—N5	1.308 (4)	C16—C17	1.369 (8)
N4—C19	1.371 (4)	C17—C18	1.391 (5)
N5—N6	1.366 (3)	C17—H17	0.9300
N6—C20	1.360 (4)	C18—H18	0.9300
N6—C22	1.426 (4)	C19—C20	1.377 (4)
C1—C6	1.388 (4)	C20—C21	1.479 (4)
C1—C2	1.392 (4)	C21—H21A	0.9600
C1—C7	1.468 (4)	C21—H21B	0.9600
C2—C3	1.396 (5)	C21—H21C	0.9600
C2—H2	0.9300	C22—C27	1.363 (4)
C3—C4	1.368 (6)	C22—C23	1.378 (4)
C3—H3	0.9300	C23—C24	1.378 (5)
C4—C5	1.363 (6)	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.378 (5)
C5—C6	1.356 (5)	C24—H24	0.9300
C5—H5	0.9300	C25—C26	1.362 (5)
C6—H6	0.9300	C25—C28	1.508 (5)
C7—C8	1.353 (4)	C26—C27	1.374 (4)
C8—H8	0.9300	C26—H26	0.9300
C10—C13	1.498 (4)	C27—H27	0.9300
C10—C11	1.526 (4)	C28—H28A	0.9600
C10—H10	0.9800	C28—H28B	0.9600
C11—C12	1.498 (4)	C28—H28C	0.9600

C8—S1—C9	88.34 (15)	C18—C13—C10	122.3 (3)
C9—N1—C7	109.7 (2)	C14—C13—C10	119.6 (4)
C9—N2—N3	119.3 (2)	C15—C14—C13	121.0 (5)
C9—N2—C10	122.5 (3)	C15—C14—H14	119.5
N3—N2—C10	113.1 (2)	C13—C14—H14	119.5
C12—N3—N2	108.2 (2)	C16—C15—C14	121.5 (6)
N5—N4—C19	108.9 (2)	C16—C15—H15	119.2
N4—N5—N6	107.2 (2)	C14—C15—H15	119.2
C20—N6—N5	111.0 (2)	C15—C16—F1	122.5 (8)
C20—N6—C22	130.8 (3)	C15—C16—C17	121.0 (5)
N5—N6—C22	118.1 (2)	F1—C16—C17	116.5 (8)
C6—C1—C2	117.7 (3)	C16—C17—C18	118.1 (5)
C6—C1—C7	121.9 (3)	C16—C17—H17	120.9
C2—C1—C7	120.4 (3)	C18—C17—H17	120.9
C1—C2—C3	120.1 (4)	C13—C18—C17	120.3 (4)
C1—C2—H2	120.0	C13—C18—H18	119.8
C3—C2—H2	120.0	C17—C18—H18	119.8
C4—C3—C2	120.4 (4)	N4—C19—C20	109.1 (3)
C4—C3—H3	119.8	N4—C19—C12	119.9 (3)
C2—C3—H3	119.8	C20—C19—C12	131.0 (3)
C5—C4—C3	119.2 (4)	N6—C20—C19	103.9 (3)
C5—C4—H4	120.4	N6—C20—C21	125.5 (3)
C3—C4—H4	120.4	C19—C20—C21	130.6 (3)
C6—C5—C4	121.3 (4)	C20—C21—H21A	109.5
C6—C5—H5	119.3	C20—C21—H21B	109.5
C4—C5—H5	119.3	H21A—C21—H21B	109.5
C5—C6—C1	121.3 (3)	C20—C21—H21C	109.5
C5—C6—H6	119.4	H21A—C21—H21C	109.5
C1—C6—H6	119.4	H21B—C21—H21C	109.5
C8—C7—N1	114.8 (3)	C27—C22—C23	119.7 (3)
C8—C7—C1	126.6 (3)	C27—C22—N6	120.9 (3)
N1—C7—C1	118.6 (3)	C23—C22—N6	119.5 (3)
C7—C8—S1	111.2 (2)	C22—C23—C24	118.7 (3)
C7—C8—H8	124.4	C22—C23—H23	120.6
S1—C8—H8	124.4	C24—C23—H23	120.6
N1—C9—N2	122.9 (3)	C25—C24—C23	122.8 (3)
N1—C9—S1	115.9 (2)	C25—C24—H24	118.6
N2—C9—S1	121.1 (2)	C23—C24—H24	118.6
N2—C10—C13	113.1 (3)	C26—C25—C24	116.3 (3)
N2—C10—C11	100.4 (2)	C26—C25—C28	122.6 (4)
C13—C10—C11	115.1 (3)	C24—C25—C28	121.1 (4)
N2—C10—H10	109.3	C25—C26—C27	122.7 (4)
C13—C10—H10	109.3	C25—C26—H26	118.6
C11—C10—H10	109.3	C27—C26—H26	118.6
C12—C11—C10	103.3 (3)	C22—C27—C26	119.8 (3)
C12—C11—H11A	111.1	C22—C27—H27	120.1
C10—C11—H11A	111.1	C26—C27—H27	120.1
C12—C11—H11B	111.1	C25—C28—H28A	109.5
C10—C11—H11B	111.1	C25—C28—H28B	109.5
H11A—C11—H11B	109.1	H28A—C28—H28B	109.5
N3—C12—C19	123.9 (3)	C25—C28—H28C	109.5
N3—C12—C11	113.4 (3)	H28A—C28—H28C	109.5
C19—C12—C11	122.7 (3)	H28B—C28—H28C	109.5
C18—C13—C14	118.0 (4)

C9—N2—N3—C12	−164.7 (3)	C11—C10—C13—C18	80.7 (4)
C10—N2—N3—C12	−9.1 (4)	N2—C10—C13—C14	149.4 (3)
C19—N4—N5—N6	1.0 (4)	C11—C10—C13—C14	−96.0 (4)
N4—N5—N6—C20	−0.7 (4)	C18—C13—C14—C15	−2.0 (6)
N4—N5—N6—C22	−178.1 (3)	C10—C13—C14—C15	174.9 (4)
C6—C1—C2—C3	0.7 (5)	C13—C14—C15—C16	2.4 (9)
C7—C1—C2—C3	179.5 (3)	C14—C15—C16—F1	−179.2 (4)
C1—C2—C3—C4	−0.5 (6)	C14—C15—C16—C17	−1.5 (10)
C2—C3—C4—C5	−0.4 (7)	C15—C16—C17—C18	0.2 (9)
C3—C4—C5—C6	1.1 (7)	F1—C16—C17—C18	178.1 (4)
C4—C5—C6—C1	−0.8 (6)	C14—C13—C18—C17	0.7 (6)
C2—C1—C6—C5	−0.1 (5)	C10—C13—C18—C17	−176.1 (3)
C7—C1—C6—C5	−178.8 (3)	C16—C17—C18—C13	0.2 (6)
C9—N1—C7—C8	1.2 (4)	N5—N4—C19—C20	−1.0 (4)
C9—N1—C7—C1	−178.0 (2)	N5—N4—C19—C12	178.2 (3)
C6—C1—C7—C8	−2.0 (5)	N3—C12—C19—N4	−173.3 (3)
C2—C1—C7—C8	179.4 (3)	C11—C12—C19—N4	8.5 (5)
C6—C1—C7—N1	177.2 (3)	N3—C12—C19—C20	5.6 (6)
C2—C1—C7—N1	−1.5 (4)	C11—C12—C19—C20	−172.6 (3)
N1—C7—C8—S1	−0.5 (4)	N5—N6—C20—C19	0.1 (4)
C1—C7—C8—S1	178.6 (2)	C22—N6—C20—C19	177.1 (3)
C9—S1—C8—C7	−0.2 (2)	N5—N6—C20—C21	−177.9 (3)
C7—N1—C9—N2	175.1 (3)	C22—N6—C20—C21	−0.9 (5)
C7—N1—C9—S1	−1.3 (3)	N4—C19—C20—N6	0.5 (4)
N3—N2—C9—N1	169.3 (3)	C12—C19—C20—N6	−178.5 (3)
C10—N2—C9—N1	16.1 (5)	N4—C19—C20—C21	178.4 (3)
N3—N2—C9—S1	−14.5 (4)	C12—C19—C20—C21	−0.7 (6)
C10—N2—C9—S1	−167.7 (2)	C20—N6—C22—C27	47.5 (5)
C8—S1—C9—N1	0.9 (2)	N5—N6—C22—C27	−135.7 (3)
C8—S1—C9—N2	−175.6 (3)	C20—N6—C22—C23	−132.9 (4)
C9—N2—C10—C13	−69.1 (4)	N5—N6—C22—C23	44.0 (4)
N3—N2—C10—C13	136.2 (3)	C27—C22—C23—C24	−1.7 (5)
C9—N2—C10—C11	167.7 (3)	N6—C22—C23—C24	178.7 (3)
N3—N2—C10—C11	13.0 (3)	C22—C23—C24—C25	0.1 (6)
N2—C10—C11—C12	−11.4 (3)	C23—C24—C25—C26	1.1 (6)
C13—C10—C11—C12	−133.1 (3)	C23—C24—C25—C28	−179.0 (3)
N2—N3—C12—C19	−177.9 (3)	C24—C25—C26—C27	−0.8 (6)
N2—N3—C12—C11	0.5 (4)	C28—C25—C26—C27	179.2 (3)
C10—C11—C12—N3	7.6 (4)	C23—C22—C27—C26	1.9 (5)
C10—C11—C12—C19	−174.0 (3)	N6—C22—C27—C26	−178.4 (3)
N2—C10—C13—C18	−33.9 (4)	C25—C26—C27—C22	−0.7 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C22–C27 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···S1ⁱ	0.93	2.87	3.743 (4)	156
C24—H24···F1ⁱⁱ	0.93	2.55	3.476 (5)	177
C28—H28B···F1ⁱⁱⁱ	0.96	2.53	3.308 (5)	138
C27—H27···Cg1ⁱ	0.93	2.75	3.518 (4)	141
C14—H14···Cg2ⁱⁱ	0.93	2.85	3.756 (5)	164

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₃FN₆S
M_r	494.58
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	17.7373 (18), 7.8367 (7), 19.4159 (18)
β (°)	109.323 (11)
V (Å³)	2546.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
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	0.901, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	16284, 5871, 2694
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.232, 1.06
No. of reflections	5871
No. of parameters	328
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.38

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C22–C27 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···S1ⁱ	0.93	2.87	3.743 (4)	156
C24—H24···F1ⁱⁱ	0.93	2.55	3.476 (5)	177
C28—H28B···F1ⁱⁱⁱ	0.96	2.53	3.308 (5)	138
C27—H27···Cg1ⁱ	0.93	2.75	3.518 (4)	141
C14—H14···Cg2ⁱⁱ	0.93	2.85	3.756 (5)	164

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

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/03).

References

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
Dong, W.-J., Cui, F.-H., Gao, Z.-L., Li, R.-S., Shen, G.-L. & Dong, H.-S. (2011). J. Heterocycl. Chem. 48, 1154–1160. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 4| April 2013| Page o618

doi:10.1107/S1600536813008179

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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