3-(4-Chloro­phen­yl)-5-(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide

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

doi:10.1107/S1600536813004492

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Pages o414-o415

doi:10.1107/S1600536813004492

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3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide

Bakr F. Abdel-Wahab,^a ‡ Hanan A. Mohamed,^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 14 February 2013; accepted 14 February 2013; online 20 February 2013)

In the title compound, C₁₆H₁₃ClFN₃S, the pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. The chloro- and fluorobenzene rings are twisted out of the plane of the pyrazole ring [dihedral angles = 15.12 (11) and 80.55 (10)°, respectively]. The amine group is orientated towards a ring N atom, forming an intramolecular N—H⋯N hydrogen bond. This H atom also forms a hydrogen bond to the F atom, which along with N—H⋯S hydrogen bonding leads to a supramolecular chain along the c axis. Connections between chains of the type Cl⋯π lead to a layer in the bc plane.

Related literature

For the biological activity of pyrazolin-1-ylthiazoles, see: Abdel-Wahab et al. (2009 , 2012 ); Chimenti et al. (2010 ). For related structures, see: Chantrapromma et al. (2012 ); Abdel-Wahab et al. (2013 ).

Experimental

Crystal data

C₁₆H₁₃ClFN₃S
M_r = 333.80
Monoclinic, P 2₁ /c
a = 14.5402 (9) Å
b = 11.2700 (8) Å
c = 9.5169 (6) Å
β = 103.850 (6)°
V = 1514.17 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.40 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 = 0.898, T_max = 1.000
10191 measured reflections
3478 independent reflections
2570 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.111
S = 1.01
3478 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H31⋯N1	0.88	2.24	2.617 (2)	106
N3—H31⋯F1ⁱ	0.88	2.41	3.257 (2)	163
N3—H32⋯S1ⁱⁱ	0.88	2.81	3.5203 (19)	139
C4—Cl1⋯Cg1ⁱⁱⁱ	1.735 (2)	3.9240 (12)	4.183 (2)	86.17 (17)
Symmetry codes: (i) x, y, z+1; (ii) $[x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 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/S1600536813004492/hg5293sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004492/hg5293Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813004492/hg5293Isup3.cml

checkCIF report

Comment top

Pyrazolin-1-ylthiazole derivatives are known to exhibit biological potential (Abdel-Wahab et al., 2012; Abdel-Wahab et al., 2009; Chimenti et al., 2010) and motivated the investigation of the title compound, (I).

The central pyrazolyl ring in (I), Fig. 1, adopts an envelope conformation with the methine-C9 atom being the flap atom. The amine group is orientated towards the ring-N2 atom, forming a hydrogen bond, Table 1, assisted by the near co-planar relationship between the thioamide group and the pyrazolyl ring with the N1—N2—C16—N3 torsion angle being -0.7 (2)°. Both the chloro- and fluoro-benzene rings are twisted out of the least-squares plane through the five-membered ring, forming dihedral angles of 15.12 (11) and 80.55 (10)°, respectively. Quite similar conformations have been observed in related structures bearing two six-membered rings (Chantrapromma et al., 2012; Abdel-Wahab et al., 2013).

In the crystal packing, the amine-H31 atom participating in the intramolecular N—H···N hydrogen bond also forms a hydrogen bond to the F1 atom, Table 1. This interaction along with an N—H···S hydrogen bond leads to a supramolecular chain along the c axis, Table 1. Chains are connected into a layer in the bc plane by Cl···π interactions, Fig. 2 and Table 1. Layers stack along the a axis without specific interactions between them, Fig. 3.

Related literature top

For the biological activity of pyrazolin-1-ylthiazoles, see: Abdel-Wahab et al. (2009, 2012); Chimenti et al. (2010). For related structures, see: Chantrapromma et al. (2012); Abdel-Wahab et al. (2013).

Experimental top

To a suspension of (E)-1-(4-chlorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one (1 mmol, 0.26 g) and sodium hydroxide (2.5 mmol, 1.0 g) in ethanol (20 ml), thiosemicarbazide (1.2 mmol, 0.11 g) was added. The mixture was refluxed for 12 h, then left to cool. The solid product was filtered off, washed with ethanol and dried. Recrystallization was by slow evaporation of its DMF solution.

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 supramolecular layer in the bc plane in (I) mediated by N—H···S, N—H···F and Cl···π interactions, shown as orange, blue and purple dashed lines, respectively.
	Fig. 3. A view of the crystal packing in projection down the c axis. The N—H···S, N—H···F and Cl···π interactions are shown as orange, blue and purple dashed lines, respectively.

3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide top

Crystal data top

C₁₆H₁₃ClFN₃S	F(000) = 688
M_r = 333.80	D_x = 1.464 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2717 reflections
a = 14.5402 (9) Å	θ = 2.9–27.5°
b = 11.2700 (8) Å	µ = 0.40 mm⁻¹
c = 9.5169 (6) Å	T = 295 K
β = 103.850 (6)°	Prism, colourless
V = 1514.17 (17) Å³	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3478 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2570 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ω scan	h = −15→18
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −14→11
T_min = 0.898, T_max = 1.000	l = −12→12
10191 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0432P)² + 0.4541P] where P = (F_o² + 2F_c²)/3
3478 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₆H₁₃ClFN₃S	V = 1514.17 (17) Å³
M_r = 333.80	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.5402 (9) Å	µ = 0.40 mm⁻¹
b = 11.2700 (8) Å	T = 295 K
c = 9.5169 (6) Å	0.40 × 0.30 × 0.20 mm
β = 103.850 (6)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3478 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2570 reflections with I > 2σ(I)
T_min = 0.898, T_max = 1.000	R_int = 0.031
10191 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.01	Δρ_max = 0.19 e Å⁻³
3478 reflections	Δρ_min = −0.28 e Å⁻³
199 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
Cl1	0.54931 (5)	0.65490 (7)	0.48095 (8)	0.0811 (3)
S1	−0.01110 (4)	1.16708 (5)	−0.15948 (5)	0.04527 (17)
F1	0.27125 (11)	1.14248 (13)	−0.60633 (13)	0.0658 (4)
N1	0.20984 (11)	1.00001 (15)	0.08010 (15)	0.0379 (4)
N2	0.13525 (11)	1.03202 (14)	−0.03592 (15)	0.0368 (4)
N3	0.10065 (13)	1.17944 (16)	0.10514 (17)	0.0463 (4)
H31	0.1483	1.1542	0.1741	0.056*
H32	0.0669	1.2407	0.1207	0.056*
C1	0.31834 (13)	0.83907 (18)	0.1544 (2)	0.0381 (4)
C2	0.37595 (15)	0.9020 (2)	0.2678 (2)	0.0498 (5)
H2	0.3661	0.9829	0.2772	0.060*
C3	0.44754 (16)	0.8454 (2)	0.3665 (2)	0.0559 (6)
H3	0.4860	0.8879	0.4419	0.067*
C4	0.46163 (14)	0.7261 (2)	0.3529 (2)	0.0505 (6)
C5	0.40755 (15)	0.6624 (2)	0.2408 (3)	0.0533 (6)
H5	0.4187	0.5819	0.2314	0.064*
C6	0.33602 (14)	0.7194 (2)	0.1414 (2)	0.0476 (5)
H6	0.2993	0.6766	0.0647	0.057*
C7	0.23925 (13)	0.89711 (18)	0.05223 (19)	0.0366 (4)
C8	0.18302 (14)	0.84371 (17)	−0.08689 (19)	0.0394 (4)
H8A	0.1424	0.7802	−0.0687	0.047*
H8B	0.2242	0.8136	−0.1452	0.047*
C9	0.12464 (13)	0.95057 (17)	−0.15998 (18)	0.0365 (4)
H9	0.0581	0.9282	−0.1966	0.044*
C10	0.16342 (12)	1.00448 (17)	−0.27969 (17)	0.0330 (4)
C11	0.23938 (13)	1.08168 (18)	−0.24895 (19)	0.0403 (5)
H11	0.2656	1.1032	−0.1534	0.048*
C12	0.27723 (14)	1.12774 (19)	−0.3580 (2)	0.0442 (5)
H12	0.3288	1.1791	−0.3370	0.053*
C13	0.23618 (15)	1.09503 (19)	−0.4978 (2)	0.0430 (5)
C14	0.16111 (15)	1.01890 (19)	−0.53370 (19)	0.0463 (5)
H14	0.1350	0.9983	−0.6296	0.056*
C15	0.12497 (14)	0.97331 (18)	−0.42252 (19)	0.0400 (4)
H15	0.0741	0.9210	−0.4442	0.048*
C16	0.07946 (13)	1.12480 (17)	−0.02300 (19)	0.0352 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0556 (4)	0.0764 (5)	0.0967 (5)	0.0061 (3)	−0.0106 (3)	0.0318 (4)
S1	0.0410 (3)	0.0485 (4)	0.0446 (3)	0.0047 (2)	0.0067 (2)	0.0045 (2)
F1	0.0922 (10)	0.0679 (10)	0.0444 (7)	−0.0139 (8)	0.0304 (7)	0.0066 (6)
N1	0.0384 (8)	0.0440 (10)	0.0306 (7)	0.0025 (7)	0.0068 (6)	0.0007 (7)
N2	0.0406 (8)	0.0402 (10)	0.0295 (7)	0.0046 (7)	0.0080 (6)	−0.0024 (6)
N3	0.0537 (10)	0.0438 (10)	0.0409 (9)	0.0073 (8)	0.0106 (7)	−0.0069 (7)
C1	0.0368 (10)	0.0409 (12)	0.0380 (9)	0.0007 (8)	0.0116 (7)	0.0033 (8)
C2	0.0544 (13)	0.0427 (13)	0.0485 (12)	0.0034 (10)	0.0045 (9)	−0.0004 (9)
C3	0.0520 (13)	0.0587 (16)	0.0488 (12)	−0.0014 (11)	−0.0041 (10)	0.0004 (10)
C4	0.0349 (10)	0.0542 (15)	0.0606 (13)	0.0006 (10)	0.0078 (9)	0.0182 (11)
C5	0.0412 (11)	0.0397 (13)	0.0768 (15)	0.0024 (10)	0.0094 (10)	0.0066 (11)
C6	0.0400 (11)	0.0449 (13)	0.0565 (12)	−0.0026 (9)	0.0091 (9)	−0.0029 (10)
C7	0.0360 (10)	0.0397 (12)	0.0361 (9)	−0.0015 (8)	0.0129 (7)	0.0007 (8)
C8	0.0462 (11)	0.0372 (11)	0.0355 (9)	−0.0004 (9)	0.0111 (8)	−0.0002 (8)
C9	0.0364 (9)	0.0401 (11)	0.0324 (9)	−0.0022 (8)	0.0074 (7)	−0.0048 (8)
C10	0.0329 (9)	0.0343 (10)	0.0307 (8)	0.0027 (8)	0.0056 (7)	−0.0015 (7)
C11	0.0412 (10)	0.0458 (12)	0.0313 (9)	−0.0044 (9)	0.0033 (7)	−0.0028 (8)
C12	0.0431 (11)	0.0462 (13)	0.0437 (11)	−0.0074 (9)	0.0114 (8)	−0.0010 (9)
C13	0.0575 (12)	0.0397 (12)	0.0354 (10)	0.0030 (10)	0.0181 (9)	0.0038 (8)
C14	0.0605 (13)	0.0466 (13)	0.0289 (9)	−0.0014 (10)	0.0053 (8)	−0.0020 (8)
C15	0.0440 (11)	0.0380 (11)	0.0350 (9)	−0.0046 (9)	0.0037 (8)	−0.0030 (8)
C16	0.0378 (9)	0.0351 (11)	0.0358 (9)	−0.0042 (8)	0.0148 (7)	0.0024 (8)

Geometric parameters (Å, º) top

Cl1—C4	1.735 (2)	C5—H5	0.9300
S1—C16	1.6821 (19)	C6—H6	0.9300
F1—C13	1.365 (2)	C7—C8	1.505 (2)
N1—C7	1.285 (2)	C8—C9	1.540 (3)
N1—N2	1.397 (2)	C8—H8A	0.9700
N2—C16	1.347 (2)	C8—H8B	0.9700
N2—C9	1.474 (2)	C9—C10	1.514 (3)
N3—C16	1.335 (2)	C9—H9	0.9800
N3—H31	0.8800	C10—C11	1.381 (3)
N3—H32	0.8800	C10—C15	1.386 (2)
C1—C6	1.384 (3)	C11—C12	1.386 (3)
C1—C2	1.392 (3)	C11—H11	0.9300
C1—C7	1.470 (3)	C12—C13	1.373 (3)
C2—C3	1.380 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.366 (3)
C3—C4	1.371 (3)	C14—C15	1.388 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.367 (3)	C15—H15	0.9300
C5—C6	1.385 (3)

C7—N1—N2	107.67 (15)	C7—C8—H8B	111.4
C16—N2—N1	119.92 (15)	C9—C8—H8B	111.4
C16—N2—C9	127.35 (15)	H8A—C8—H8B	109.2
N1—N2—C9	112.63 (14)	N2—C9—C10	111.49 (15)
C16—N3—H31	120.0	N2—C9—C8	100.63 (13)
C16—N3—H32	120.0	C10—C9—C8	112.91 (15)
H31—N3—H32	120.0	N2—C9—H9	110.5
C6—C1—C2	118.41 (18)	C10—C9—H9	110.5
C6—C1—C7	120.48 (18)	C8—C9—H9	110.5
C2—C1—C7	121.10 (19)	C11—C10—C15	118.82 (17)
C3—C2—C1	120.5 (2)	C11—C10—C9	121.08 (15)
C3—C2—H2	119.7	C15—C10—C9	120.06 (17)
C1—C2—H2	119.7	C10—C11—C12	121.19 (17)
C4—C3—C2	119.7 (2)	C10—C11—H11	119.4
C4—C3—H3	120.2	C12—C11—H11	119.4
C2—C3—H3	120.2	C13—C12—C11	117.83 (19)
C3—C4—C5	121.16 (19)	C13—C12—H12	121.1
C3—C4—Cl1	119.23 (17)	C11—C12—H12	121.1
C5—C4—Cl1	119.61 (19)	C14—C13—F1	118.55 (17)
C4—C5—C6	119.1 (2)	C14—C13—C12	123.16 (18)
C4—C5—H5	120.4	F1—C13—C12	118.28 (19)
C6—C5—H5	120.4	C13—C14—C15	117.89 (17)
C5—C6—C1	121.1 (2)	C13—C14—H14	121.1
C5—C6—H6	119.5	C15—C14—H14	121.1
C1—C6—H6	119.5	C10—C15—C14	121.10 (18)
N1—C7—C1	120.74 (17)	C10—C15—H15	119.4
N1—C7—C8	113.88 (16)	C14—C15—H15	119.4
C1—C7—C8	125.33 (18)	N3—C16—N2	115.42 (16)
C7—C8—C9	102.08 (15)	N3—C16—S1	122.79 (16)
C7—C8—H8A	111.4	N2—C16—S1	121.78 (14)
C9—C8—H8A	111.4

C7—N1—N2—C16	167.15 (16)	C16—N2—C9—C8	−159.69 (18)
C7—N1—N2—C9	−9.4 (2)	N1—N2—C9—C8	16.59 (19)
C6—C1—C2—C3	−1.4 (3)	C7—C8—C9—N2	−16.22 (18)
C7—C1—C2—C3	177.32 (19)	C7—C8—C9—C10	102.72 (17)
C1—C2—C3—C4	−0.3 (3)	N2—C9—C10—C11	31.9 (2)
C2—C3—C4—C5	1.8 (4)	C8—C9—C10—C11	−80.5 (2)
C2—C3—C4—Cl1	−177.91 (17)	N2—C9—C10—C15	−150.42 (17)
C3—C4—C5—C6	−1.4 (4)	C8—C9—C10—C15	97.1 (2)
Cl1—C4—C5—C6	178.23 (17)	C15—C10—C11—C12	−0.1 (3)
C4—C5—C6—C1	−0.3 (3)	C9—C10—C11—C12	177.60 (18)
C2—C1—C6—C5	1.7 (3)	C10—C11—C12—C13	0.6 (3)
C7—C1—C6—C5	−177.00 (19)	C11—C12—C13—C14	−0.7 (3)
N2—N1—C7—C1	179.67 (16)	C11—C12—C13—F1	178.21 (18)
N2—N1—C7—C8	−2.9 (2)	F1—C13—C14—C15	−178.68 (19)
C6—C1—C7—N1	165.27 (18)	C12—C13—C14—C15	0.2 (3)
C2—C1—C7—N1	−13.4 (3)	C11—C10—C15—C14	−0.4 (3)
C6—C1—C7—C8	−11.9 (3)	C9—C10—C15—C14	−178.12 (18)
C2—C1—C7—C8	169.41 (19)	C13—C14—C15—C10	0.3 (3)
N1—C7—C8—C9	12.9 (2)	N1—N2—C16—N3	−0.7 (2)
C1—C7—C8—C9	−169.76 (17)	C9—N2—C16—N3	175.38 (17)
C16—N2—C9—C10	80.3 (2)	N1—N2—C16—S1	179.89 (13)
N1—N2—C9—C10	−103.38 (17)	C9—N2—C16—S1	−4.1 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H31···N1	0.88	2.24	2.617 (2)	106
N3—H31···F1ⁱ	0.88	2.41	3.257 (2)	163
N3—H32···S1ⁱⁱ	0.88	2.81	3.5203 (19)	139
C4—Cl1···Cg1ⁱⁱⁱ	1.74 (1)	3.92 (1)	4.183 (2)	86 (1)

Symmetry codes: (i) x, y, z+1; (ii) x, −y+5/2, z+1/2; (iii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClFN₃S
M_r	333.80
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	14.5402 (9), 11.2700 (8), 9.5169 (6)
β (°)	103.850 (6)
V (Å³)	1514.17 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
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	0.898, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10191, 3478, 2570
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.111, 1.01
No. of reflections	3478
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.28

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 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H31···N1	0.88	2.24	2.617 (2)	106
N3—H31···F1ⁱ	0.88	2.41	3.257 (2)	163
N3—H32···S1ⁱⁱ	0.88	2.81	3.5203 (19)	139
C4—Cl1···Cg1ⁱⁱⁱ	1.735 (2)	3.9240 (12)	4.183 (2)	86.17 (7)

Symmetry codes: (i) x, y, z+1; (ii) x, −y+5/2, z+1/2; (iii) x, −y+1/2, 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
Abdel-Wahab, B. F., Mohamed, H. A., Khidre, R. E., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o386. Google Scholar
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Chantrapromma, S., Nonthason, P., Suwunwong, T. & Fun, H.-K. (2012). Acta Cryst. E68, o830–o831. CSD CrossRef IUCr Journals Google Scholar
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Volume 69| Part 3| March 2013| Pages o414-o415

doi:10.1107/S1600536813004492

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

3-(4-Chloro­phen­yl)-5-(4-fluoro­phen­yl)-4,5-di­hydro-1H-pyrazole-1-carbo­thio­amide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide