5-(4-Fluoro­phen­yl)-3-[5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]-4,5-dihydro-1H-pyrazole-1-carbothio­amide

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

doi:10.1107/S1600536812024245

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1954-o1955

doi:10.1107/S1600536812024245

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5-(4-Fluorophenyl)-3-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]-4,5-dihydro-1H-pyrazole-1-carbothioamide

Bakr F. Abdel-Wahab,^a ‡ Ehab Abdel-Latif,^b Seik Weng Ng ^c,^d and Edward R. T. Tiekink ^c ^*

^aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt, ^bDepartment of Chemistry, Faculty of Science, Mansoura University, ET-35516 Mansoura, Egypt, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry 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, C₂₀H₁₉FN₆S, the pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The dihedral angle between the least-squares plane through the pyrazole and triazole rings is 7.59 (9)°, and the triazole and attached benzene ring form a dihedral angle of 74.79 (9)°. The thiourea group is coplanar with the pyrazole ring [N—N—C—S torsion angle = −179.93 (11)°], which enables the formation of an intramolecular N—H⋯N hydrogen bond. In the crystal, inversion-related molecules associate via N—H⋯S hydrogen bonds and eight-membered {⋯HNCS}₂ synthons feature in the crystal packing. These synthons are connected into supramolecular chains along the a axis via N—H⋯F hydrogen bonds, and the chains are consolidated into layers in the ab plane via C—H⋯S and C—H⋯F contacts.

Related literature

For the biological activity of pyrazolyl-1,2,3-triazoles, see: Abdel-Wahab et al. (2012a ); Booth & Ross (1982 ); Curran (1982 ). For a related pyrazolyl-1,2,3-triazole structure, see: Abdel-Wahab et al. (2012b ).

Experimental

Crystal data

C₂₀H₁₉FN₆S
M_r = 394.47
Monoclinic, P 2₁ /c
a = 9.4388 (4) Å
b = 6.5476 (3) Å
c = 32.1483 (18) Å
β = 91.288 (4)°
V = 1986.31 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 100 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 = 0.855, T_max = 1.000
7765 measured reflections
4551 independent reflections
3809 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.109
S = 1.02
4551 reflections
263 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯S1ⁱ	0.89 (2)	2.432 (19)	3.3159 (14)	172.7 (16)
N1—H2N⋯F1ⁱⁱ	0.86 (2)	2.29 (2)	2.9940 (18)	138.9 (17)
N1—H2N⋯N3	0.86 (2)	2.30 (2)	2.6554 (19)	104.9 (15)
C3—H3A⋯S1ⁱⁱⁱ	0.99	2.87	3.8390 (19)	166
C9—H9⋯S1^iv	0.95	2.83	3.5595 (18)	135
C15—H15⋯F1^v	0.95	2.41	3.2502 (19)	148
Symmetry codes: (i) -x+1, -y+3, -z+1; (ii) x+1, y, z; (iii) x, y-1, z; (iv) -x, -y+2, -z+1; (v) x+1, y-1, 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 (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/S1600536812024245/su2439sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812024245/su2439Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812024245/su2439Isup3.cml

checkCIF report

Comment top

In continuation of structural studies of related drug candidates (Abdel-Wahab et al., 2012b), the title compound, (I), was investigated crystallographically. This compound is of interest owing to the established biological activities exhibited by pyrazolyl-1,2,3-triazoles (Abdel-Wahab et al., 2012a; Booth & Ross, 1982; Curran, 1982).

The pyrazole ring in (I), Fig. 1, adopts an envelope conformation (r.m.s. deviation = 0.138 Å) with the methine-C2 atom being the flap atom. The dihedral angle between the least-squares plane through this ring and the adjacent triazole ring is 7.59 (9)°. The benzene ring connected to the triazole ring is twisted out of its plane, forming a dihedral angle of 74.79 (9)°. The N3—N2—C1—S1 torsion angle of -179.93 (11)° indicates that the thiourea moiety is coplanar with the pyrazole ring. This arrangement coupled with the orientation of the amino group towards the ring enables the formation of an intramolecular N—H···N hydrogen bond (Table 1).

In the crystal, centrosymmetrically related molecules associate via N—H···S hydrogen bonds and eight-membered {···HNCS}₂ synthons feature in the crystal packing (Table 1). These are connected into supramolecular chains along the a axis via N—H···F hydrogen bonds (Fig. 2 and Table 1). Chains are connected into layers in the ab plane via C—H···S and C—H···F contacts (Table 1). Layers inter-digitate along the c axis with no specific interactions between them (Fig. 3).

Related literature top

For the biological activity of pyrazolyl-1,2,3-triazoles, see: Abdel-Wahab et al. (2012a); Booth & Ross (1982); Curran (1982). For a related pyrazolyl-1,2,3-triazole structure, see: Abdel-Wahab et al. (2012b).

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 of a supramolecular chain along the a axis in (I). The N—H···S and N—H···F hydrogen bonds are shown as blue and orange dashed lines, respectively.
	Fig. 3. A view in projection down the b axis of the unit-cell contents for (I) highlighting the inter-digitation of layers along the c axis. The N—H···S, N—H···F, C—H···S and C—H···F interactions are shown as blue, orange, purple and brown dashed lines, respectively.

5-(4-Fluorophenyl)-3-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol- 4-yl]-4,5-dihydro-1H-pyrazole-1-carbothioamide top

Crystal data top

C₂₀H₁₉FN₆S	F(000) = 824
M_r = 394.47	D_x = 1.319 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3598 reflections
a = 9.4388 (4) Å	θ = 2.2–27.5°
b = 6.5476 (3) Å	µ = 0.19 mm⁻¹
c = 32.1483 (18) Å	T = 100 K
β = 91.288 (4)°	Prism, light-brown
V = 1986.31 (17) Å³	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4551 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3809 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.027
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.5°
ω scans	h = −11→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −8→8
T_min = 0.855, T_max = 1.000	l = −23→41
7765 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.045P)² + 1.138P] where P = (F_o² + 2F_c²)/3
4551 reflections	(Δ/σ)_max = 0.002
263 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₀H₁₉FN₆S	V = 1986.31 (17) Å³
M_r = 394.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4388 (4) Å	µ = 0.19 mm⁻¹
b = 6.5476 (3) Å	T = 100 K
c = 32.1483 (18) Å	0.40 × 0.30 × 0.20 mm
β = 91.288 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4551 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3809 reflections with I > 2σ(I)
T_min = 0.855, T_max = 1.000	R_int = 0.027
7765 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.64 e Å⁻³
4551 reflections	Δρ_min = −0.36 e Å⁻³
263 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.32997 (4)	1.28074 (6)	0.507140 (13)	0.01661 (12)
F1	−0.23235 (10)	1.32770 (17)	0.39047 (3)	0.0253 (3)
N1	0.53882 (15)	1.2902 (2)	0.45302 (5)	0.0181 (3)
N2	0.38250 (13)	1.0266 (2)	0.44567 (4)	0.0137 (3)
N3	0.45951 (13)	0.9562 (2)	0.41184 (4)	0.0145 (3)
N4	0.40790 (15)	0.4715 (2)	0.35943 (5)	0.0212 (3)
N5	0.47668 (16)	0.3904 (2)	0.32855 (5)	0.0224 (3)
N6	0.57249 (14)	0.5319 (2)	0.31626 (4)	0.0161 (3)
C1	0.42324 (16)	1.1970 (2)	0.46636 (5)	0.0139 (3)
C2	0.25153 (16)	0.9101 (2)	0.45166 (5)	0.0139 (3)
H2	0.2393	0.8789	0.4818	0.017*
C3	0.28474 (17)	0.7137 (3)	0.42742 (5)	0.0162 (3)
H3A	0.3146	0.6017	0.4463	0.019*
H3B	0.2023	0.6684	0.4102	0.019*
C4	0.40479 (16)	0.7836 (3)	0.40082 (5)	0.0145 (3)
C5	0.12296 (16)	1.0241 (2)	0.43419 (5)	0.0136 (3)
C6	0.13589 (17)	1.1894 (3)	0.40729 (5)	0.0170 (3)
H6	0.2272	1.2330	0.3992	0.020*
C7	0.01603 (17)	1.2911 (3)	0.39217 (5)	0.0183 (4)
H7	0.0241	1.4039	0.3738	0.022*
C8	−0.11438 (17)	1.2240 (3)	0.40457 (5)	0.0177 (4)
C9	−0.13193 (17)	1.0592 (3)	0.43024 (5)	0.0200 (4)
H9	−0.2238	1.0148	0.4376	0.024*
C10	−0.01149 (17)	0.9592 (3)	0.44518 (5)	0.0176 (3)
H10	−0.0210	0.8450	0.4631	0.021*
C11	0.45981 (17)	0.6634 (3)	0.36697 (5)	0.0157 (3)
C12	0.56581 (17)	0.7042 (3)	0.33933 (5)	0.0158 (3)
C13	0.65699 (19)	0.8859 (3)	0.33351 (6)	0.0245 (4)
H13A	0.6911	0.8880	0.3049	0.037*
H13B	0.7380	0.8799	0.3531	0.037*
H13C	0.6021	1.0100	0.3387	0.037*
C14	0.66475 (17)	0.4832 (3)	0.28258 (5)	0.0167 (3)
C15	0.77454 (18)	0.3469 (3)	0.28951 (5)	0.0204 (4)
H15	0.7917	0.2913	0.3165	0.025*
C16	0.85941 (19)	0.2924 (3)	0.25663 (6)	0.0229 (4)
H16	0.9354	0.1995	0.2613	0.027*
C17	0.83530 (18)	0.3714 (3)	0.21690 (5)	0.0207 (4)
C18	0.72555 (19)	0.5103 (3)	0.21112 (6)	0.0260 (4)
H18	0.7092	0.5685	0.1844	0.031*
C19	0.63922 (19)	0.5658 (3)	0.24361 (5)	0.0234 (4)
H19	0.5635	0.6594	0.2391	0.028*
C20	0.9250 (2)	0.3050 (3)	0.18119 (6)	0.0324 (5)
H20A	1.0108	0.2375	0.1920	0.049*
H20B	0.9514	0.4247	0.1648	0.049*
H20C	0.8710	0.2096	0.1635	0.049*
H1N	0.5662 (19)	1.407 (3)	0.4648 (6)	0.020 (5)*
H2N	0.574 (2)	1.255 (3)	0.4297 (7)	0.027 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0194 (2)	0.0157 (2)	0.0149 (2)	−0.00300 (17)	0.00448 (15)	−0.00283 (16)
F1	0.0177 (5)	0.0359 (6)	0.0223 (5)	0.0063 (5)	−0.0003 (4)	0.0081 (5)
N1	0.0174 (7)	0.0180 (8)	0.0191 (8)	−0.0041 (6)	0.0050 (6)	−0.0068 (6)
N2	0.0125 (6)	0.0151 (7)	0.0137 (7)	−0.0008 (5)	0.0024 (5)	−0.0030 (6)
N3	0.0149 (6)	0.0154 (7)	0.0132 (7)	0.0016 (6)	0.0022 (5)	−0.0015 (6)
N4	0.0287 (8)	0.0162 (7)	0.0190 (7)	−0.0038 (6)	0.0068 (6)	−0.0044 (6)
N5	0.0291 (8)	0.0177 (7)	0.0208 (8)	−0.0071 (6)	0.0080 (6)	−0.0044 (6)
N6	0.0203 (7)	0.0133 (7)	0.0147 (7)	−0.0028 (6)	0.0027 (5)	−0.0007 (6)
C1	0.0145 (7)	0.0131 (8)	0.0141 (8)	0.0020 (6)	−0.0026 (6)	0.0011 (6)
C2	0.0159 (8)	0.0118 (7)	0.0142 (8)	−0.0031 (6)	0.0014 (6)	0.0004 (6)
C3	0.0180 (8)	0.0137 (8)	0.0170 (8)	−0.0008 (7)	0.0025 (6)	−0.0006 (7)
C4	0.0155 (7)	0.0143 (8)	0.0138 (8)	0.0019 (6)	0.0001 (6)	0.0013 (6)
C5	0.0153 (7)	0.0136 (8)	0.0121 (7)	−0.0015 (6)	0.0011 (6)	−0.0023 (6)
C6	0.0150 (8)	0.0186 (8)	0.0174 (8)	−0.0042 (7)	0.0019 (6)	−0.0003 (7)
C7	0.0204 (8)	0.0179 (8)	0.0166 (8)	−0.0010 (7)	0.0004 (6)	0.0041 (7)
C8	0.0148 (8)	0.0230 (9)	0.0152 (8)	0.0036 (7)	−0.0012 (6)	0.0003 (7)
C9	0.0142 (8)	0.0270 (10)	0.0189 (8)	−0.0034 (7)	0.0033 (6)	0.0027 (7)
C10	0.0182 (8)	0.0187 (8)	0.0161 (8)	−0.0029 (7)	0.0017 (6)	0.0021 (7)
C11	0.0180 (8)	0.0132 (8)	0.0157 (8)	−0.0006 (6)	0.0001 (6)	−0.0010 (6)
C12	0.0188 (8)	0.0137 (8)	0.0150 (8)	0.0003 (7)	0.0000 (6)	−0.0032 (7)
C13	0.0273 (9)	0.0177 (9)	0.0290 (10)	−0.0070 (8)	0.0093 (8)	−0.0067 (8)
C14	0.0204 (8)	0.0151 (8)	0.0148 (8)	−0.0022 (7)	0.0033 (6)	−0.0033 (7)
C15	0.0252 (9)	0.0213 (9)	0.0148 (8)	0.0012 (7)	0.0008 (7)	0.0016 (7)
C16	0.0236 (9)	0.0239 (9)	0.0214 (9)	0.0059 (8)	0.0021 (7)	0.0015 (8)
C17	0.0239 (9)	0.0207 (9)	0.0177 (8)	0.0020 (7)	0.0039 (7)	−0.0039 (7)
C18	0.0330 (10)	0.0292 (10)	0.0158 (9)	0.0075 (8)	0.0030 (7)	0.0024 (8)
C19	0.0272 (9)	0.0240 (9)	0.0192 (9)	0.0104 (8)	0.0020 (7)	0.0019 (8)
C20	0.0372 (11)	0.0379 (12)	0.0223 (10)	0.0130 (9)	0.0089 (8)	0.0000 (9)

Geometric parameters (Å, º) top

S1—C1	1.6873 (17)	C7—C8	1.374 (2)
F1—C8	1.3724 (19)	C7—H7	0.9500
N1—C1	1.329 (2)	C8—C9	1.371 (2)
N1—H1N	0.89 (2)	C9—C10	1.389 (2)
N1—H2N	0.86 (2)	C9—H9	0.9500
N2—C1	1.350 (2)	C10—H10	0.9500
N2—N3	1.3996 (18)	C11—C12	1.379 (2)
N2—C2	1.469 (2)	C12—C13	1.483 (2)
N3—C4	1.289 (2)	C13—H13A	0.9800
N4—N5	1.311 (2)	C13—H13B	0.9800
N4—C11	1.368 (2)	C13—H13C	0.9800
N5—N6	1.360 (2)	C14—C19	1.381 (2)
N6—C12	1.352 (2)	C14—C15	1.382 (2)
N6—C14	1.441 (2)	C15—C16	1.387 (2)
C2—C5	1.521 (2)	C15—H15	0.9500
C2—C3	1.539 (2)	C16—C17	1.392 (2)
C2—H2	1.0000	C16—H16	0.9500
C3—C4	1.506 (2)	C17—C18	1.388 (3)
C3—H3A	0.9900	C17—C20	1.505 (2)
C3—H3B	0.9900	C18—C19	1.387 (2)
C4—C11	1.449 (2)	C18—H18	0.9500
C5—C10	1.391 (2)	C19—H19	0.9500
C5—C6	1.392 (2)	C20—H20A	0.9800
C6—C7	1.391 (2)	C20—H20B	0.9800
C6—H6	0.9500	C20—H20C	0.9800

C1—N1—H1N	119.3 (12)	C8—C9—C10	118.08 (15)
C1—N1—H2N	119.6 (14)	C8—C9—H9	121.0
H1N—N1—H2N	119.4 (19)	C10—C9—H9	121.0
C1—N2—N3	120.50 (13)	C9—C10—C5	120.82 (16)
C1—N2—C2	126.55 (13)	C9—C10—H10	119.6
N3—N2—C2	112.60 (12)	C5—C10—H10	119.6
C4—N3—N2	106.88 (13)	N4—C11—C12	109.01 (14)
N5—N4—C11	108.96 (14)	N4—C11—C4	119.94 (15)
N4—N5—N6	106.73 (13)	C12—C11—C4	131.01 (16)
C12—N6—N5	111.69 (13)	N6—C12—C11	103.62 (14)
C12—N6—C14	129.31 (14)	N6—C12—C13	124.45 (15)
N5—N6—C14	119.00 (13)	C11—C12—C13	131.93 (16)
N1—C1—N2	116.57 (15)	C12—C13—H13A	109.5
N1—C1—S1	123.20 (13)	C12—C13—H13B	109.5
N2—C1—S1	120.23 (12)	H13A—C13—H13B	109.5
N2—C2—C5	111.32 (13)	C12—C13—H13C	109.5
N2—C2—C3	100.70 (12)	H13A—C13—H13C	109.5
C5—C2—C3	113.13 (13)	H13B—C13—H13C	109.5
N2—C2—H2	110.4	C19—C14—C15	120.95 (16)
C5—C2—H2	110.4	C19—C14—N6	119.95 (15)
C3—C2—H2	110.4	C15—C14—N6	119.05 (15)
C4—C3—C2	101.42 (13)	C14—C15—C16	119.14 (16)
C4—C3—H3A	111.5	C14—C15—H15	120.4
C2—C3—H3A	111.5	C16—C15—H15	120.4
C4—C3—H3B	111.5	C15—C16—C17	121.23 (17)
C2—C3—H3B	111.5	C15—C16—H16	119.4
H3A—C3—H3B	109.3	C17—C16—H16	119.4
N3—C4—C11	122.33 (15)	C18—C17—C16	118.19 (16)
N3—C4—C3	114.34 (14)	C18—C17—C20	121.20 (17)
C11—C4—C3	123.26 (15)	C16—C17—C20	120.61 (16)
C10—C5—C6	119.23 (15)	C19—C18—C17	121.34 (17)
C10—C5—C2	118.75 (15)	C19—C18—H18	119.3
C6—C5—C2	122.02 (14)	C17—C18—H18	119.3
C7—C6—C5	120.48 (15)	C14—C19—C18	119.14 (17)
C7—C6—H6	119.8	C14—C19—H19	120.4
C5—C6—H6	119.8	C18—C19—H19	120.4
C8—C7—C6	118.18 (16)	C17—C20—H20A	109.5
C8—C7—H7	120.9	C17—C20—H20B	109.5
C6—C7—H7	120.9	H20A—C20—H20B	109.5
C9—C8—F1	118.69 (14)	C17—C20—H20C	109.5
C9—C8—C7	123.19 (16)	H20A—C20—H20C	109.5
F1—C8—C7	118.12 (15)	H20B—C20—H20C	109.5

C1—N2—N3—C4	174.29 (14)	C6—C5—C10—C9	−1.1 (3)
C2—N2—N3—C4	−12.04 (17)	C2—C5—C10—C9	179.58 (15)
C11—N4—N5—N6	−0.27 (19)	N5—N4—C11—C12	0.2 (2)
N4—N5—N6—C12	0.23 (19)	N5—N4—C11—C4	−177.76 (15)
N4—N5—N6—C14	179.55 (14)	N3—C4—C11—N4	172.91 (15)
N3—N2—C1—N1	−0.5 (2)	C3—C4—C11—N4	−3.8 (2)
C2—N2—C1—N1	−173.19 (15)	N3—C4—C11—C12	−4.6 (3)
N3—N2—C1—S1	−179.93 (11)	C3—C4—C11—C12	178.72 (17)
C2—N2—C1—S1	7.3 (2)	N5—N6—C12—C11	−0.08 (18)
C1—N2—C2—C5	72.6 (2)	C14—N6—C12—C11	−179.32 (16)
N3—N2—C2—C5	−100.65 (15)	N5—N6—C12—C13	179.88 (16)
C1—N2—C2—C3	−167.24 (15)	C14—N6—C12—C13	0.6 (3)
N3—N2—C2—C3	19.54 (16)	N4—C11—C12—N6	−0.08 (18)
N2—C2—C3—C4	−18.17 (15)	C4—C11—C12—N6	177.61 (17)
C5—C2—C3—C4	100.72 (15)	N4—C11—C12—C13	179.96 (18)
N2—N3—C4—C11	−178.76 (14)	C4—C11—C12—C13	−2.4 (3)
N2—N3—C4—C3	−1.78 (18)	C12—N6—C14—C19	−76.7 (2)
C2—C3—C4—N3	13.53 (18)	N5—N6—C14—C19	104.1 (2)
C2—C3—C4—C11	−169.51 (15)	C12—N6—C14—C15	106.0 (2)
N2—C2—C5—C10	−165.88 (14)	N5—N6—C14—C15	−73.2 (2)
C3—C2—C5—C10	81.57 (18)	C19—C14—C15—C16	−0.3 (3)
N2—C2—C5—C6	14.8 (2)	N6—C14—C15—C16	176.99 (16)
C3—C2—C5—C6	−97.72 (18)	C14—C15—C16—C17	−0.4 (3)
C10—C5—C6—C7	1.2 (2)	C15—C16—C17—C18	1.4 (3)
C2—C5—C6—C7	−179.49 (15)	C15—C16—C17—C20	−177.77 (18)
C5—C6—C7—C8	0.1 (3)	C16—C17—C18—C19	−1.7 (3)
C6—C7—C8—C9	−1.6 (3)	C20—C17—C18—C19	177.47 (19)
C6—C7—C8—F1	178.40 (15)	C15—C14—C19—C18	0.0 (3)
F1—C8—C9—C10	−178.27 (15)	N6—C14—C19—C18	−177.25 (16)
C7—C8—C9—C10	1.7 (3)	C17—C18—C19—C14	1.0 (3)
C8—C9—C10—C5	−0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1ⁱ	0.89 (2)	2.432 (19)	3.3159 (14)	172.7 (16)
N1—H2N···F1ⁱⁱ	0.86 (2)	2.29 (2)	2.9940 (18)	138.9 (17)
N1—H2N···N3	0.86 (2)	2.30 (2)	2.6554 (19)	104.9 (15)
C3—H3A···S1ⁱⁱⁱ	0.99	2.87	3.8390 (19)	166
C9—H9···S1^iv	0.95	2.83	3.5595 (18)	135
C15—H15···F1^v	0.95	2.41	3.2502 (19)	148

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉FN₆S
M_r	394.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.4388 (4), 6.5476 (3), 32.1483 (18)
β (°)	91.288 (4)
V (Å³)	1986.31 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
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	0.855, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7765, 4551, 3809
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.109, 1.02
No. of reflections	4551
No. of parameters	263
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.36

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

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1ⁱ	0.89 (2)	2.432 (19)	3.3159 (14)	172.7 (16)
N1—H2N···F1ⁱⁱ	0.86 (2)	2.29 (2)	2.9940 (18)	138.9 (17)
N1—H2N···N3	0.86 (2)	2.30 (2)	2.6554 (19)	104.9 (15)
C3—H3A···S1ⁱⁱⁱ	0.99	2.87	3.8390 (19)	166
C9—H9···S1^iv	0.95	2.83	3.5595 (18)	135
C15—H15···F1^v	0.95	2.41	3.2502 (19)	148

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

Footnotes

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

Acknowledgements

The authors thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research Scheme (grant No. UM.C/HIR/MOHE/SC/12).

References

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., Mohamed, H. A., Ng, S. W. & Tiekink, E. R. T. (2012b). Acta Cryst. E68, o1956–o1957. CSD CrossRef IUCr Journals Google Scholar
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Booth, J. H. & Ross, A. S. (1982). US Patent 4336375. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Curran, W. V. (1982). US Patent 4334062. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef 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 68| Part 6| June 2012| Pages o1954-o1955

doi:10.1107/S1600536812024245

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

5-(4-Fluoro­phen­yl)-3-[5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]-4,5-di­hydro-1H-pyrazole-1-carbo­thio­amide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

5-(4-Fluorophenyl)-3-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]-4,5-dihydro-1H-pyrazole-1-carbothioamide