4-{1-[4-(4-Bromo­phen­yl)-1,3-thia­zol-2-yl]-5-(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazol-3-yl}-5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazole

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

doi:10.1107/S1600536812024257

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1956-o1957

doi:10.1107/S1600536812024257

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4-{1-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-3-yl}-5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazole

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 26 May 2012; accepted 27 May 2012; online 31 May 2012)

In the title compound, C₂₈H₂₂BrFN₆S, the central pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The dihedral angles between the least-squares plane through this ring and the adjacent thiazole [18.81 (15)°] and triazole [1.83 (16)°] rings indicate a twist in the molecule. A further twist is evident by the dihedral angle of 64.48 (16)° between the triazole ring and the attached benzene ring. In the crystal, C—H⋯N, C—H⋯F, C—H⋯π and π–π interactions [occurring between the thiazole and triazole rings, centroid–centroid distance = 3.571 (2) Å] link molecules into a three-dimensional architecture. The sample studied was a non-merohedral twin; the minor twin component refined to 47.16 (7)%.

Related literature

For the biological activity of related compounds, see: Abdel-Wahab et al. (2009 , 2012a ). For a related pyrazolyl-1,2,3-triazole structure, see: Abdel-Wahab et al. (2012b ). For the deconvolution of twinned data, see: Spek (2009 ).

Experimental

Crystal data

C₂₈H₂₂BrFN₆S
M_r = 573.49
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.3476 (7) Å
b = 14.0549 (8) Å
c = 15.954 (7) Å
V = 2544.5 (12) Å³
Z = 4
Mo Kα radiation
μ = 1.74 mm⁻¹
T = 100 K
0.40 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.695, T_max = 1.000
7265 measured reflections
5293 independent reflections
4819 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.077
S = 1.02
5293 reflections
336 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.50 e Å⁻³
Absolute structure: Flack (1983 ), 2028 Friedel pairs
Flack parameter: 0.001 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C23–C28 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N2ⁱ	1.00	2.58	3.488 (4)	151
C27—H27⋯F1ⁱⁱ	0.95	2.53	3.358 (4)	146
C8—H8A⋯Cg1ⁱⁱⁱ	0.98	2.84	3.401 (3)	117
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ .

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 (Farrugia, 1997 ) 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/S1600536812024257/su2440sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812024257/su2440Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812024257/su2440Isup3.cml

checkCIF report

Comment top

The crystal structure determination of the title compound, 4-(4-bromophenyl)-2-(5-(4-fluorophenyl)-3-(5-methyl-1-p-tolyl-1H-1,2,3-triazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazole (I), was investigated in relation to the established biological activities exhibited by 3-(benzofuran-2-yl)-4,5-dihydro-5-phenyl-1-(4-phenylthiazol-2-yl)-1H-pyrazole and 1,2,3-triazol-4-yl-pyrazolylthiazoles (Abdel-Wahab et al. 2012a; Abdel-Wahab et al. 2009) and related structural studies (Abdel-Wahab et al., 2012b).

The molecule of (I), Fig. 1, comprises a sequence of three linked five-membered rings with a benzene ring linked to each of these. The central pyrazole ring (r.m.s. deviation = 0.087 Å) adopts an envelope conformation with the methine-C13 atom being the flap atom. The molecule is twisted as seen in the dihedral angles between the least-squares plane through the pyrazole ring and the thiazole (r.m.s. deviation = 0.008 Å) and triazole (r.m.s. deviation = 0.004 Å) rings are 18.81 (15) and 1.83 (16)°, respectively. While the attached benzene ring to the thiazole ring is almost co-planar [dihedral angle = 7.00 (13)°], the benzene ring linked to the triazole ring is twisted out of its plane [dihedral angle = 64.48 (16)°].

In the crystal, C—H···N and C—H···π (Table 1), as well as π—π interactions occurring between the thiazole and triazole [inter-centroid distance = 3.571 (2) Å, angle of inclination = 5.08 (15)° for symmetry operation: -1/2 + x, 3/2 - y, -z] link molecules into layers in the ac plane. These layers are linked by C—H···F interactions (Fig. 2 and Table 1).

Related literature top

For the biological activity of related compounds, see: Abdel-Wahab et al. (2009, 2012a). For a related pyrazolyl-1,2,3-triazole structure, see: Abdel-Wahab et al. (2012b). For the deconvolution of twinned data, see: Spek (2009).

Experimental top

The title compound was prepared according to the reported method (Abdel-Wahab et al., 2012a). 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 (Farrugia, 1997) 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 70% probability level.
	Fig. 2. A view in projection down the c axis of the unit-cell contents for (I). The C—H···N, C—H···F, C—H···π and π—π interactions are shown as blue, orange, purple and brown dashed lines, respectively.

4-{1-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-5-(4-fluorophenyl)-4,5-dihydro- 1H-pyrazol-3-yl}-5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazole top

Crystal data top

C₂₈H₂₂BrFN₆S	F(000) = 1168
M_r = 573.49	D_x = 1.497 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3622 reflections
a = 11.3476 (7) Å	θ = 2.6–27.5°
b = 14.0549 (8) Å	µ = 1.74 mm⁻¹
c = 15.954 (7) Å	T = 100 K
V = 2544.5 (12) Å³	Prism, light-brown
Z = 4	0.40 × 0.20 × 0.10 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5293 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4819 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.6°
ω scan	h = −14→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −17→12
T_min = 0.695, T_max = 1.000	l = −20→11
7265 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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0325P)² + 0.2812P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
5293 reflections	Δρ_max = 0.36 e Å⁻³
336 parameters	Δρ_min = −0.50 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2028 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.001 (7)

Crystal data top

C₂₈H₂₂BrFN₆S	V = 2544.5 (12) Å³
M_r = 573.49	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.3476 (7) Å	µ = 1.74 mm⁻¹
b = 14.0549 (8) Å	T = 100 K
c = 15.954 (7) Å	0.40 × 0.20 × 0.10 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5293 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	4819 reflections with I > 2σ(I)
T_min = 0.695, T_max = 1.000	R_int = 0.029
7265 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.077	Δρ_max = 0.36 e Å⁻³
S = 1.02	Δρ_min = −0.50 e Å⁻³
5293 reflections	Absolute structure: Flack (1983), 2028 Friedel pairs
336 parameters	Absolute structure parameter: 0.001 (7)
0 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
Br1	0.23440 (3)	0.94410 (2)	−0.361341 (19)	0.02124 (8)
S1	0.66530 (6)	0.86176 (5)	0.08004 (5)	0.01822 (17)
F1	0.94395 (17)	1.26252 (12)	−0.25372 (13)	0.0294 (5)
N1	1.2170 (2)	0.77775 (16)	0.21438 (15)	0.0152 (5)
N2	1.2929 (2)	0.78394 (16)	0.14807 (16)	0.0174 (5)
N3	1.2310 (2)	0.81441 (16)	0.08489 (15)	0.0154 (5)
N4	0.9210 (2)	0.87452 (17)	0.06940 (16)	0.0171 (5)
N5	0.8648 (2)	0.91513 (18)	0.00017 (16)	0.0170 (5)
N6	0.6859 (2)	0.91897 (16)	−0.07364 (16)	0.0155 (5)
C1	1.2602 (3)	0.7492 (2)	0.29537 (18)	0.0167 (6)
C2	1.2594 (3)	0.8146 (2)	0.36070 (19)	0.0208 (6)
H2	1.2265	0.8761	0.3532	0.025*
C3	1.3073 (3)	0.7883 (2)	0.4366 (2)	0.0255 (7)
H3	1.3062	0.8322	0.4818	0.031*
C4	1.3573 (3)	0.6990 (2)	0.4485 (2)	0.0247 (7)
C5	1.3549 (3)	0.6346 (2)	0.3825 (2)	0.0247 (8)
H5	1.3869	0.5728	0.3902	0.030*
C6	1.3067 (3)	0.6589 (2)	0.3059 (2)	0.0204 (7)
H6	1.3055	0.6144	0.2611	0.024*
C7	1.4158 (3)	0.6738 (3)	0.5301 (2)	0.0366 (9)
H7A	1.3946	0.6086	0.5458	0.055*
H7B	1.3895	0.7179	0.5739	0.055*
H7C	1.5016	0.6785	0.5238	0.055*
C8	1.0046 (3)	0.8013 (2)	0.2515 (2)	0.0178 (6)
H8A	1.0048	0.7410	0.2823	0.027*
H8B	0.9310	0.8072	0.2199	0.027*
H8C	1.0112	0.8543	0.2912	0.027*
C9	1.1057 (3)	0.8035 (2)	0.1929 (2)	0.0151 (6)
C10	1.1170 (3)	0.8273 (2)	0.10935 (19)	0.0142 (6)
C11	1.0306 (3)	0.8628 (2)	0.05071 (18)	0.0138 (6)
C12	1.0619 (3)	0.8935 (2)	−0.03664 (19)	0.0170 (6)
H12A	1.1013	0.8416	−0.0678	0.020*
H12B	1.1138	0.9501	−0.0361	0.020*
C13	0.9411 (2)	0.9169 (2)	−0.07472 (19)	0.0148 (6)
H13	0.9171	0.8647	−0.1138	0.018*
C14	0.9378 (2)	1.0115 (2)	−0.12096 (18)	0.0159 (6)
C15	0.8894 (3)	1.0932 (2)	−0.0868 (2)	0.0196 (7)
H15	0.8547	1.0910	−0.0326	0.024*
C16	0.8913 (3)	1.1791 (2)	−0.1314 (2)	0.0241 (7)
H16	0.8576	1.2353	−0.1085	0.029*
C17	0.9427 (3)	1.1797 (2)	−0.2088 (2)	0.0208 (7)
C18	0.9940 (3)	1.1004 (2)	−0.2437 (2)	0.0188 (7)
H18	1.0310	1.1036	−0.2971	0.023*
C19	0.9906 (3)	1.0161 (2)	−0.1994 (2)	0.0177 (6)
H19	1.0247	0.9604	−0.2229	0.021*
C20	0.7446 (3)	0.90135 (18)	−0.00607 (17)	0.0152 (6)
C21	0.5397 (3)	0.8702 (2)	0.0193 (2)	0.0190 (7)
H21	0.4623	0.8560	0.0382	0.023*
C22	0.5671 (3)	0.8999 (2)	−0.0593 (2)	0.0171 (7)
C23	0.4858 (2)	0.91170 (19)	−0.1308 (2)	0.0155 (6)
C24	0.5272 (2)	0.9486 (2)	−0.20621 (19)	0.0180 (6)
H24	0.6073	0.9676	−0.2105	0.022*
C25	0.4538 (3)	0.9581 (2)	−0.27493 (19)	0.0197 (7)
H25	0.4831	0.9831	−0.3262	0.024*
C26	0.3367 (3)	0.9305 (2)	−0.26774 (19)	0.0168 (6)
C27	0.2930 (3)	0.8929 (2)	−0.1943 (2)	0.0204 (7)
H27	0.2129	0.8736	−0.1906	0.025*
C28	0.3677 (3)	0.8836 (2)	−0.1253 (2)	0.0197 (7)
H28	0.3383	0.8581	−0.0743	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02349 (14)	0.02282 (14)	0.01741 (15)	−0.00056 (13)	−0.00417 (13)	0.00095 (13)
S1	0.0157 (3)	0.0244 (4)	0.0145 (4)	−0.0021 (3)	0.0021 (3)	0.0024 (3)
F1	0.0288 (10)	0.0224 (9)	0.0372 (12)	−0.0012 (9)	−0.0056 (10)	0.0159 (9)
N1	0.0152 (12)	0.0186 (11)	0.0117 (13)	−0.0003 (10)	−0.0012 (10)	−0.0026 (10)
N2	0.0187 (12)	0.0181 (11)	0.0153 (14)	0.0005 (10)	0.0004 (11)	−0.0009 (11)
N3	0.0176 (12)	0.0168 (11)	0.0119 (12)	0.0000 (11)	−0.0006 (11)	0.0005 (10)
N4	0.0181 (12)	0.0197 (12)	0.0137 (14)	0.0004 (11)	−0.0021 (11)	0.0045 (11)
N5	0.0126 (11)	0.0257 (13)	0.0128 (13)	−0.0008 (10)	0.0031 (10)	0.0055 (11)
N6	0.0126 (11)	0.0174 (12)	0.0166 (13)	0.0018 (10)	0.0022 (10)	0.0014 (10)
C1	0.0150 (13)	0.0222 (13)	0.0130 (14)	−0.0009 (13)	−0.0013 (13)	0.0050 (11)
C2	0.0214 (14)	0.0231 (13)	0.0178 (15)	0.0020 (12)	−0.0002 (16)	−0.0005 (13)
C3	0.0273 (17)	0.0338 (18)	0.0153 (17)	−0.0043 (15)	−0.0011 (14)	−0.0030 (14)
C4	0.0226 (16)	0.0355 (18)	0.0161 (17)	−0.0044 (15)	−0.0018 (13)	0.0095 (15)
C5	0.0236 (15)	0.0221 (15)	0.028 (2)	0.0002 (14)	−0.0025 (14)	0.0073 (14)
C6	0.0188 (14)	0.0219 (15)	0.0204 (17)	−0.0012 (13)	−0.0020 (13)	−0.0002 (13)
C7	0.033 (2)	0.057 (2)	0.020 (2)	−0.0065 (19)	−0.0102 (17)	0.0115 (18)
C8	0.0159 (13)	0.0236 (15)	0.0139 (15)	0.0004 (12)	0.0026 (12)	0.0021 (13)
C9	0.0143 (14)	0.0143 (14)	0.0166 (16)	−0.0011 (12)	0.0012 (12)	−0.0013 (12)
C10	0.0175 (13)	0.0129 (13)	0.0123 (15)	−0.0016 (12)	0.0007 (12)	0.0018 (11)
C11	0.0160 (13)	0.0145 (13)	0.0109 (15)	−0.0034 (12)	0.0020 (12)	−0.0032 (12)
C12	0.0147 (14)	0.0203 (15)	0.0161 (16)	0.0012 (12)	0.0024 (13)	0.0046 (13)
C13	0.0146 (13)	0.0171 (14)	0.0128 (15)	−0.0004 (12)	0.0007 (12)	0.0010 (12)
C14	0.0116 (13)	0.0197 (14)	0.0165 (17)	−0.0018 (12)	−0.0034 (12)	0.0045 (12)
C15	0.0190 (14)	0.0231 (15)	0.0167 (17)	0.0005 (13)	0.0012 (13)	0.0015 (13)
C16	0.0200 (14)	0.0212 (15)	0.031 (2)	0.0050 (12)	−0.0010 (16)	−0.0028 (16)
C17	0.0183 (15)	0.0195 (15)	0.0244 (18)	−0.0034 (13)	−0.0075 (14)	0.0130 (14)
C18	0.0135 (14)	0.0278 (16)	0.0152 (16)	−0.0032 (13)	−0.0026 (13)	0.0070 (14)
C19	0.0140 (14)	0.0199 (14)	0.0191 (17)	0.0012 (12)	−0.0035 (13)	−0.0010 (13)
C20	0.0152 (14)	0.0159 (12)	0.0146 (14)	0.0030 (12)	0.0020 (12)	0.0017 (11)
C21	0.0154 (14)	0.0218 (15)	0.0198 (17)	−0.0011 (13)	0.0004 (13)	0.0017 (14)
C22	0.0163 (14)	0.0161 (14)	0.0190 (17)	0.0017 (12)	−0.0014 (13)	−0.0002 (13)
C23	0.0152 (13)	0.0138 (12)	0.0175 (16)	0.0025 (11)	0.0003 (13)	0.0018 (13)
C24	0.0150 (13)	0.0164 (14)	0.0226 (16)	−0.0011 (13)	0.0009 (12)	0.0011 (14)
C25	0.0217 (14)	0.0193 (15)	0.0180 (16)	0.0031 (13)	0.0014 (13)	0.0037 (13)
C26	0.0184 (14)	0.0163 (14)	0.0158 (15)	0.0043 (13)	−0.0044 (12)	−0.0001 (12)
C27	0.0145 (15)	0.0253 (16)	0.0215 (17)	−0.0012 (12)	0.0009 (13)	−0.0001 (13)
C28	0.0185 (14)	0.0243 (15)	0.0161 (18)	0.0005 (12)	0.0029 (13)	0.0016 (13)

Geometric parameters (Å, º) top

Br1—C26	1.901 (3)	C8—H8C	0.9800
S1—C21	1.728 (3)	C9—C10	1.381 (4)
S1—C20	1.734 (3)	C10—C11	1.445 (4)
F1—C17	1.367 (3)	C11—C12	1.501 (4)
N1—C9	1.358 (4)	C12—C13	1.535 (4)
N1—N2	1.367 (3)	C12—H12A	0.9900
N1—C1	1.439 (4)	C12—H12B	0.9900
N2—N3	1.300 (3)	C13—C14	1.521 (4)
N3—C10	1.363 (4)	C13—H13	1.0000
N4—C11	1.290 (4)	C14—C19	1.389 (4)
N4—N5	1.397 (3)	C14—C15	1.385 (4)
N5—C20	1.381 (4)	C15—C16	1.402 (4)
N5—C13	1.475 (4)	C15—H15	0.9500
N6—C20	1.291 (4)	C16—C17	1.365 (5)
N6—C22	1.394 (4)	C16—H16	0.9500
C1—C6	1.384 (4)	C17—C18	1.376 (4)
C1—C2	1.390 (4)	C18—C19	1.380 (4)
C2—C3	1.377 (4)	C18—H18	0.9500
C2—H2	0.9500	C19—H19	0.9500
C3—C4	1.390 (5)	C21—C22	1.357 (4)
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.388 (5)	C22—C23	1.476 (4)
C4—C7	1.504 (4)	C23—C24	1.392 (4)
C5—C6	1.383 (4)	C23—C28	1.400 (4)
C5—H5	0.9500	C24—C25	1.383 (4)
C6—H6	0.9500	C24—H24	0.9500
C7—H7A	0.9800	C25—C26	1.390 (4)
C7—H7B	0.9800	C25—H25	0.9500
C7—H7C	0.9800	C26—C27	1.378 (4)
C8—C9	1.480 (4)	C27—C28	1.396 (4)
C8—H8A	0.9800	C27—H27	0.9500
C8—H8B	0.9800	C28—H28	0.9500

C21—S1—C20	87.81 (15)	C13—C12—H12B	111.3
C9—N1—N2	112.0 (2)	H12A—C12—H12B	109.2
C9—N1—C1	128.1 (3)	N5—C13—C14	113.2 (2)
N2—N1—C1	119.9 (2)	N5—C13—C12	101.5 (2)
N3—N2—N1	106.3 (2)	C14—C13—C12	113.6 (2)
N2—N3—C10	109.5 (2)	N5—C13—H13	109.4
C11—N4—N5	108.0 (2)	C14—C13—H13	109.4
C20—N5—N4	116.8 (2)	C12—C13—H13	109.4
C20—N5—C13	121.5 (3)	C19—C14—C15	119.2 (3)
N4—N5—C13	112.3 (2)	C19—C14—C13	117.9 (3)
C20—N6—C22	109.0 (2)	C15—C14—C13	122.9 (3)
C6—C1—C2	121.2 (3)	C14—C15—C16	120.5 (3)
C6—C1—N1	119.6 (3)	C14—C15—H15	119.7
C2—C1—N1	119.1 (3)	C16—C15—H15	119.7
C3—C2—C1	118.6 (3)	C17—C16—C15	118.1 (3)
C3—C2—H2	120.7	C17—C16—H16	120.9
C1—C2—H2	120.7	C15—C16—H16	120.9
C2—C3—C4	121.6 (3)	C16—C17—F1	119.0 (3)
C2—C3—H3	119.2	C16—C17—C18	122.8 (3)
C4—C3—H3	119.2	F1—C17—C18	118.2 (3)
C3—C4—C5	118.5 (3)	C17—C18—C19	118.4 (3)
C3—C4—C7	120.8 (3)	C17—C18—H18	120.8
C5—C4—C7	120.8 (3)	C19—C18—H18	120.8
C6—C5—C4	121.2 (3)	C14—C19—C18	120.9 (3)
C6—C5—H5	119.4	C14—C19—H19	119.6
C4—C5—H5	119.4	C18—C19—H19	119.6
C5—C6—C1	119.0 (3)	N6—C20—N5	122.9 (3)
C5—C6—H6	120.5	N6—C20—S1	117.1 (2)
C1—C6—H6	120.5	N5—C20—S1	120.0 (2)
C4—C7—H7A	109.5	C22—C21—S1	110.5 (2)
C4—C7—H7B	109.5	C22—C21—H21	124.7
H7A—C7—H7B	109.5	S1—C21—H21	124.7
C4—C7—H7C	109.5	C21—C22—N6	115.6 (3)
H7A—C7—H7C	109.5	C21—C22—C23	127.2 (3)
H7B—C7—H7C	109.5	N6—C22—C23	117.1 (3)
C9—C8—H8A	109.5	C24—C23—C28	118.9 (3)
C9—C8—H8B	109.5	C24—C23—C22	119.9 (3)
H8A—C8—H8B	109.5	C28—C23—C22	121.2 (3)
C9—C8—H8C	109.5	C25—C24—C23	121.2 (3)
H8A—C8—H8C	109.5	C25—C24—H24	119.4
H8B—C8—H8C	109.5	C23—C24—H24	119.4
N1—C9—C10	102.8 (3)	C24—C25—C26	118.9 (3)
N1—C9—C8	123.8 (3)	C24—C25—H25	120.6
C10—C9—C8	133.4 (3)	C26—C25—H25	120.6
N3—C10—C9	109.4 (3)	C27—C26—C25	121.4 (3)
N3—C10—C11	120.3 (3)	C27—C26—Br1	119.2 (2)
C9—C10—C11	130.2 (3)	C25—C26—Br1	119.4 (2)
N4—C11—C10	123.3 (3)	C26—C27—C28	119.2 (3)
N4—C11—C12	114.0 (3)	C26—C27—H27	120.4
C10—C11—C12	122.7 (3)	C28—C27—H27	120.4
C11—C12—C13	102.6 (2)	C27—C28—C23	120.4 (3)
C11—C12—H12A	111.3	C27—C28—H28	119.8
C13—C12—H12A	111.3	C23—C28—H28	119.8
C11—C12—H12B	111.3

C9—N1—N2—N3	0.7 (3)	C11—C12—C13—C14	132.8 (3)
C1—N1—N2—N3	−177.6 (2)	N5—C13—C14—C19	−169.6 (3)
N1—N2—N3—C10	−0.4 (3)	C12—C13—C14—C19	75.3 (3)
C11—N4—N5—C20	156.5 (3)	N5—C13—C14—C15	13.2 (4)
C11—N4—N5—C13	9.4 (3)	C12—C13—C14—C15	−101.9 (3)
C9—N1—C1—C6	118.3 (3)	C19—C14—C15—C16	1.3 (4)
N2—N1—C1—C6	−63.7 (4)	C13—C14—C15—C16	178.5 (3)
C9—N1—C1—C2	−64.7 (4)	C14—C15—C16—C17	−0.5 (5)
N2—N1—C1—C2	113.3 (3)	C15—C16—C17—F1	179.1 (3)
C6—C1—C2—C3	0.7 (5)	C15—C16—C17—C18	−1.0 (5)
N1—C1—C2—C3	−176.2 (3)	C16—C17—C18—C19	1.7 (5)
C1—C2—C3—C4	0.9 (5)	F1—C17—C18—C19	−178.5 (3)
C2—C3—C4—C5	−2.0 (5)	C15—C14—C19—C18	−0.7 (4)
C2—C3—C4—C7	176.2 (3)	C13—C14—C19—C18	−178.0 (3)
C3—C4—C5—C6	1.6 (5)	C17—C18—C19—C14	−0.8 (4)
C7—C4—C5—C6	−176.6 (3)	C22—N6—C20—N5	−178.7 (3)
C4—C5—C6—C1	0.0 (5)	C22—N6—C20—S1	−0.4 (3)
C2—C1—C6—C5	−1.2 (5)	N4—N5—C20—N6	−166.6 (3)
N1—C1—C6—C5	175.8 (3)	C13—N5—C20—N6	−22.6 (4)
N2—N1—C9—C10	−0.7 (3)	N4—N5—C20—S1	15.2 (4)
C1—N1—C9—C10	177.5 (3)	C13—N5—C20—S1	159.2 (2)
N2—N1—C9—C8	178.3 (3)	C21—S1—C20—N6	−0.3 (2)
C1—N1—C9—C8	−3.5 (5)	C21—S1—C20—N5	178.0 (2)
N2—N3—C10—C9	−0.1 (3)	C20—S1—C21—C22	1.0 (2)
N2—N3—C10—C11	178.7 (2)	S1—C21—C22—N6	−1.5 (3)
N1—C9—C10—N3	0.5 (3)	S1—C21—C22—C23	176.9 (2)
C8—C9—C10—N3	−178.4 (3)	C20—N6—C22—C21	1.2 (4)
N1—C9—C10—C11	−178.2 (3)	C20—N6—C22—C23	−177.4 (2)
C8—C9—C10—C11	2.9 (6)	C21—C22—C23—C24	176.1 (3)
N5—N4—C11—C10	176.4 (3)	N6—C22—C23—C24	−5.6 (4)
N5—N4—C11—C12	−1.1 (3)	C21—C22—C23—C28	−6.0 (5)
N3—C10—C11—N4	178.4 (3)	N6—C22—C23—C28	172.4 (3)
C9—C10—C11—N4	−3.1 (5)	C28—C23—C24—C25	0.3 (4)
N3—C10—C11—C12	−4.3 (4)	C22—C23—C24—C25	178.3 (3)
C9—C10—C11—C12	174.2 (3)	C23—C24—C25—C26	0.3 (5)
N4—C11—C12—C13	−6.8 (3)	C24—C25—C26—C27	−0.8 (5)
C10—C11—C12—C13	175.6 (2)	C24—C25—C26—Br1	179.5 (2)
C20—N5—C13—C14	79.6 (3)	C25—C26—C27—C28	0.8 (4)
N4—N5—C13—C14	−135.1 (2)	Br1—C26—C27—C28	−179.5 (2)
C20—N5—C13—C12	−158.3 (3)	C26—C27—C28—C23	−0.3 (4)
N4—N5—C13—C12	−12.9 (3)	C24—C23—C28—C27	−0.3 (4)
C11—C12—C13—N5	11.0 (3)	C22—C23—C28—C27	−178.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C23–C28 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N2ⁱ	1.00	2.58	3.488 (4)	151
C27—H27···F1ⁱⁱ	0.95	2.53	3.358 (4)	146
C8—H8A···Cg1ⁱⁱⁱ	0.98	2.84	3.401 (3)	117

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) −x+1, y−1/2, −z−1/2; (iii) −x, y+3/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₂BrFN₆S
M_r	573.49
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	11.3476 (7), 14.0549 (8), 15.954 (7)
V (Å³)	2544.5 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.74
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.695, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7265, 5293, 4819
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.077, 1.02
No. of reflections	5293
No. of parameters	336
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.50
Absolute structure	Flack (1983), 2028 Friedel pairs
Absolute structure parameter	0.001 (7)

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C23–C28 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N2ⁱ	1.00	2.58	3.488 (4)	151
C27—H27···F1ⁱⁱ	0.95	2.53	3.358 (4)	146
C8—H8A···Cg1ⁱⁱⁱ	0.98	2.84	3.401 (3)	117

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) −x+1, y−1/2, −z−1/2; (iii) −x, y+3/2, −z+1/2.

Footnotes

‡Additional correspondence author: 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. (2012a). Eur. J. Med. Chem. 52, 263–268. Web of Science CAS PubMed Google Scholar
Abdel-Wahab, B. F., Abdel-Latif, E., Ng, S. W. & Tiekink, E. R. T. (2012b). Acta Cryst. E68, o1954–o1955. CSD CrossRef IUCr Journals Google Scholar
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Pages o1956-o1957

doi:10.1107/S1600536812024257

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

4-{1-[4-(4-Bromo­phen­yl)-1,3-thia­zol-2-yl]-5-(4-fluoro­phen­yl)-4,5-di­hydro-1H-pyrazol-3-yl}-5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazole

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-{1-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-3-yl}-5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazole