5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide

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

doi:10.1107/S1600536813004194

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 3| March 2013| Pages o385-o386

doi:10.1107/S1600536813004194

Open

access

5-(4-Fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide

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

^aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt, ^bChemical Industries Division, National Research Centre, Dokki, 12622, Giza, 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 11 February 2013; accepted 12 February 2013; online 16 February 2013)

The central pyrazole ring in the title compound, C₁₇H₁₆FN₃S, adopts an envelope conformation with the methine C atom bearing the 4-fluorophenyl substituent as the flap atom. Whereas the tolyl ring is slightly twisted out of the least-squares plane through the pyrazole ring [dihedral angle = 13.51 (11)°], the fluorobenzene ring is almost perpendicular [dihedral angle = 80.21 (11)°]. The thioamide group is almost coplanar with the N—N bond of the ring [N—N—C—N torsion angle = 1.2 (3)°] and the amine group forms an intramolecular hydrogen bond with a ring N atom. In the crystal, supramolecular double layers in the bc plane are formed via N—H⋯S, N—H⋯F and C—H⋯F interactions.

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: Nonthason et al. (2011 ); Chantrapromma et al. (2012 ).

Experimental

Crystal data

C₁₇H₁₆FN₃S
M_r = 313.39
Monoclinic, P 2₁ /c
a = 14.4154 (10) Å
b = 11.3197 (9) Å
c = 9.5575 (8) Å
β = 103.991 (8)°
V = 1513.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 295 K
0.30 × 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 = 0.772, T_max = 1.000
9303 measured reflections
3500 independent reflections
2370 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.122
S = 1.04
3500 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H31⋯N2	0.88	2.23	2.611 (3)	106
N3—H31⋯F1ⁱ	0.88	2.41	3.255 (2)	162
N3—H32⋯S1ⁱⁱ	0.88	2.83	3.538 (2)	138
C16—H16B⋯F1ⁱⁱⁱ	0.96	2.55	3.478 (3)	163
Symmetry codes: (i) x, y, z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+2, -y+1, -z+1.

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/S1600536813004194/hg5291sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004194/hg5291Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813004194/hg5291Isup3.cml

checkCIF report

Comment top

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

The central pyrazolyl ring in (I), Fig. 1, adopts an envelope conformation with the methine-C7 atom being the flap atom. The tolyl ring is slightly twisted out of the least-squares plane through the pyrazolyl ring, forming a dihedral angle of 13.51 (11)°. By contrast, the fluorobenzene ring is almost perpendicular to the five-membered ring [dihedral angle = 80.21 (11)°]. Finally, the thioamide residue is co-planar with the N2—N1—C17—N3 torsion angle being 1.2 (3)°; the amine group is orientated towards the ring-N2 atom, forming a hydrogen bond, Table 1. Similar conformations have been observed in related structures bearing two six-membered rings (Nonthason et al., 2011; Chantrapromma et al., 2012).

The F atom proves to be pivotal in providing stability to the crystal structure of (I). Thus, in addition to forming an intramolecular N—H···N2 hydrogen bond, the amine-H31 atom forms a hydrogen bond to the F1 atom, Table 1. The second amine-H32 atom hydrogen bonds to a thione so that a supramolecular chain along the c axis ensues, Fig. 2. Chains stack along the b axis to form a row and centrosymmetrically related rows inter-digitate along the a axis allowing for the formation methylene-C16—H···F1 interactions and, therefore, double layers, Fig. 2.

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: Nonthason et al. (2011); Chantrapromma et al. (2012).

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-(4-chlorophenyl)ethanone (0.23 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 DMF solution of (I) which yielded colourless crystals in 61% yield. M.pt: 513–514 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) 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 50% probability level.
	Fig. 2. A view of the supramolecular chain along the c axis in (I) mediated by N—H···S and N—H···F hydrogen bonds, shown as orange and blue 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 C—H···F interactions are shown as orange, blue and pink dashed lines, respectively.

5-(4-Fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide top

Crystal data top

C₁₇H₁₆FN₃S	F(000) = 656
M_r = 313.39	D_x = 1.376 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2000 reflections
a = 14.4154 (10) Å	θ = 2.9–27.5°
b = 11.3197 (9) Å	µ = 0.22 mm⁻¹
c = 9.5575 (8) Å	T = 295 K
β = 103.991 (8)°	Prism, colourless
V = 1513.3 (2) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3500 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2370 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 = −18→17
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→14
T_min = 0.772, T_max = 1.000	l = −12→12
9303 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0448P)² + 0.2973P] where P = (F_o² + 2F_c²)/3
3500 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₇H₁₆FN₃S	V = 1513.3 (2) Å³
M_r = 313.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.4154 (10) Å	µ = 0.22 mm⁻¹
b = 11.3197 (9) Å	T = 295 K
c = 9.5575 (8) Å	0.30 × 0.20 × 0.10 mm
β = 103.991 (8)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3500 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2370 reflections with I > 2σ(I)
T_min = 0.772, T_max = 1.000	R_int = 0.038
9303 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.04	Δρ_max = 0.18 e Å⁻³
3500 reflections	Δρ_min = −0.26 e Å⁻³
200 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	0.48991 (4)	0.33372 (5)	0.33938 (6)	0.04739 (19)
F1	0.76993 (11)	0.35963 (12)	−0.10409 (14)	0.0659 (4)
N1	0.63664 (12)	0.46879 (14)	0.46526 (17)	0.0384 (4)
N2	0.71143 (11)	0.50005 (15)	0.58117 (17)	0.0391 (4)
N3	0.60198 (14)	0.32075 (15)	0.60342 (19)	0.0491 (5)
H31	0.6497	0.3462	0.6727	0.059*
H32	0.5684	0.2591	0.6181	0.059*
C1	0.73573 (16)	0.40770 (19)	0.0050 (2)	0.0445 (5)
C2	0.77815 (16)	0.3771 (2)	0.1434 (2)	0.0483 (6)
H2	0.8306	0.3266	0.1637	0.058*
C3	0.74165 (14)	0.42262 (19)	0.2528 (2)	0.0435 (5)
H3	0.7697	0.4024	0.3479	0.052*
C4	0.66378 (13)	0.49796 (17)	0.2226 (2)	0.0341 (4)
C5	0.62418 (15)	0.52828 (18)	0.0812 (2)	0.0416 (5)
H5	0.5728	0.5804	0.0602	0.050*
C6	0.65938 (16)	0.48273 (19)	−0.0307 (2)	0.0469 (5)
H6	0.6320	0.5025	−0.1262	0.056*
C7	0.62560 (14)	0.55094 (17)	0.3424 (2)	0.0376 (5)
H7	0.5584	0.5736	0.3066	0.045*
C8	0.68480 (15)	0.65640 (18)	0.4168 (2)	0.0406 (5)
H8A	0.7267	0.6865	0.3594	0.049*
H8B	0.6439	0.7198	0.4347	0.049*
C9	0.74100 (14)	0.60325 (18)	0.5553 (2)	0.0378 (5)
C10	0.82031 (14)	0.65987 (18)	0.6583 (2)	0.0381 (5)
C11	0.87678 (15)	0.5981 (2)	0.7726 (2)	0.0486 (6)
H11	0.8658	0.5179	0.7826	0.058*
C12	0.94914 (17)	0.6537 (2)	0.8718 (3)	0.0526 (6)
H12	0.9867	0.6101	0.9470	0.063*
C13	0.96669 (15)	0.7734 (2)	0.8614 (2)	0.0470 (5)
C14	0.91224 (16)	0.8339 (2)	0.7453 (3)	0.0519 (6)
H14	0.9243	0.9136	0.7342	0.062*
C15	0.83985 (15)	0.7787 (2)	0.6447 (2)	0.0470 (5)
H15	0.8041	0.8216	0.5673	0.056*
C16	1.04181 (18)	0.8345 (2)	0.9752 (3)	0.0673 (8)
H16A	1.0751	0.8910	0.9303	0.101*
H16B	1.0864	0.7772	1.0264	0.101*
H16C	1.0119	0.8744	1.0414	0.101*
C17	0.58067 (14)	0.37547 (17)	0.4763 (2)	0.0365 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0422 (3)	0.0508 (3)	0.0468 (3)	−0.0061 (3)	0.0063 (2)	−0.0054 (3)
F1	0.0882 (10)	0.0730 (9)	0.0427 (8)	0.0155 (8)	0.0279 (7)	−0.0051 (7)
N1	0.0401 (9)	0.0438 (10)	0.0305 (8)	−0.0056 (8)	0.0071 (7)	−0.0003 (7)
N2	0.0387 (9)	0.0462 (10)	0.0315 (9)	−0.0038 (8)	0.0066 (7)	−0.0025 (8)
N3	0.0545 (11)	0.0474 (10)	0.0437 (10)	−0.0086 (9)	0.0088 (9)	0.0077 (8)
C1	0.0549 (13)	0.0448 (12)	0.0370 (11)	−0.0018 (11)	0.0170 (10)	−0.0035 (10)
C2	0.0448 (12)	0.0556 (13)	0.0442 (12)	0.0135 (11)	0.0099 (10)	0.0022 (11)
C3	0.0438 (11)	0.0547 (13)	0.0296 (10)	0.0095 (11)	0.0043 (9)	0.0018 (10)
C4	0.0342 (10)	0.0357 (10)	0.0315 (10)	−0.0021 (9)	0.0062 (8)	0.0008 (8)
C5	0.0433 (11)	0.0431 (11)	0.0346 (11)	0.0075 (10)	0.0020 (9)	0.0040 (9)
C6	0.0594 (14)	0.0487 (12)	0.0283 (10)	0.0028 (11)	0.0023 (10)	0.0040 (9)
C7	0.0360 (10)	0.0428 (11)	0.0325 (10)	0.0030 (9)	0.0056 (8)	0.0044 (9)
C8	0.0455 (11)	0.0403 (11)	0.0360 (11)	0.0006 (10)	0.0100 (9)	−0.0010 (9)
C9	0.0370 (10)	0.0422 (11)	0.0359 (10)	0.0003 (10)	0.0124 (9)	−0.0027 (9)
C10	0.0362 (10)	0.0427 (11)	0.0372 (11)	−0.0007 (9)	0.0124 (9)	−0.0038 (9)
C11	0.0509 (13)	0.0447 (12)	0.0469 (13)	−0.0063 (11)	0.0052 (11)	−0.0013 (10)
C12	0.0521 (13)	0.0542 (14)	0.0449 (13)	0.0011 (12)	−0.0010 (11)	−0.0012 (11)
C13	0.0385 (11)	0.0510 (13)	0.0509 (13)	0.0004 (10)	0.0098 (10)	−0.0134 (11)
C14	0.0434 (12)	0.0413 (12)	0.0695 (16)	−0.0045 (11)	0.0106 (12)	−0.0052 (11)
C15	0.0423 (12)	0.0465 (12)	0.0513 (13)	0.0009 (10)	0.0093 (10)	0.0026 (11)
C16	0.0527 (14)	0.0653 (16)	0.0745 (18)	−0.0040 (13)	−0.0025 (13)	−0.0231 (14)
C17	0.0384 (10)	0.0378 (11)	0.0365 (11)	0.0033 (9)	0.0151 (9)	−0.0034 (9)

Geometric parameters (Å, º) top

S1—C17	1.679 (2)	C7—C8	1.538 (3)
F1—C1	1.369 (2)	C7—H7	0.9800
N1—C17	1.349 (2)	C8—C9	1.501 (3)
N1—N2	1.392 (2)	C8—H8A	0.9700
N1—C7	1.476 (2)	C8—H8B	0.9700
N2—C9	1.288 (3)	C9—C10	1.464 (3)
N3—C17	1.332 (2)	C10—C11	1.383 (3)
N3—H31	0.8800	C10—C15	1.386 (3)
N3—H32	0.8800	C11—C12	1.381 (3)
C1—C2	1.361 (3)	C11—H11	0.9300
C1—C6	1.367 (3)	C12—C13	1.386 (3)
C2—C3	1.379 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.377 (3)
C3—C4	1.383 (3)	C13—C16	1.505 (3)
C3—H3	0.9300	C14—C15	1.385 (3)
C4—C5	1.377 (3)	C14—H14	0.9300
C4—C7	1.509 (3)	C15—H15	0.9300
C5—C6	1.389 (3)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600

C17—N1—N2	119.99 (16)	C9—C8—H8B	111.3
C17—N1—C7	127.16 (16)	C7—C8—H8B	111.3
N2—N1—C7	112.76 (15)	H8A—C8—H8B	109.2
C9—N2—N1	107.83 (16)	N2—C9—C10	120.57 (18)
C17—N3—H31	120.0	N2—C9—C8	113.58 (17)
C17—N3—H32	120.0	C10—C9—C8	125.81 (18)
H31—N3—H32	120.0	C11—C10—C15	118.05 (19)
C2—C1—F1	118.6 (2)	C11—C10—C9	121.63 (19)
C2—C1—C6	123.1 (2)	C15—C10—C9	120.31 (19)
F1—C1—C6	118.25 (19)	C12—C11—C10	121.0 (2)
C1—C2—C3	118.5 (2)	C12—C11—H11	119.5
C1—C2—H2	120.7	C10—C11—H11	119.5
C3—C2—H2	120.7	C11—C12—C13	121.1 (2)
C2—C3—C4	120.74 (19)	C11—C12—H12	119.4
C2—C3—H3	119.6	C13—C12—H12	119.4
C4—C3—H3	119.6	C14—C13—C12	117.8 (2)
C5—C4—C3	118.76 (18)	C14—C13—C16	121.6 (2)
C5—C4—C7	120.31 (17)	C12—C13—C16	120.6 (2)
C3—C4—C7	120.86 (17)	C13—C14—C15	121.5 (2)
C4—C5—C6	121.39 (19)	C13—C14—H14	119.3
C4—C5—H5	119.3	C15—C14—H14	119.3
C6—C5—H5	119.3	C14—C15—C10	120.6 (2)
C1—C6—C5	117.44 (19)	C14—C15—H15	119.7
C1—C6—H6	121.3	C10—C15—H15	119.7
C5—C6—H6	121.3	C13—C16—H16A	109.5
N1—C7—C4	111.36 (16)	C13—C16—H16B	109.5
N1—C7—C8	100.38 (15)	H16A—C16—H16B	109.5
C4—C7—C8	113.31 (16)	C13—C16—H16C	109.5
N1—C7—H7	110.5	H16A—C16—H16C	109.5
C4—C7—H7	110.5	H16B—C16—H16C	109.5
C8—C7—H7	110.5	N3—C17—N1	115.16 (18)
C9—C8—C7	102.56 (16)	N3—C17—S1	122.98 (16)
C9—C8—H8A	111.3	N1—C17—S1	121.85 (15)
C7—C8—H8A	111.3

C17—N1—N2—C9	−167.33 (17)	N1—N2—C9—C10	−179.64 (16)
C7—N1—N2—C9	9.5 (2)	N1—N2—C9—C8	2.3 (2)
F1—C1—C2—C3	−177.94 (19)	C7—C8—C9—N2	−12.1 (2)
C6—C1—C2—C3	0.9 (3)	C7—C8—C9—C10	169.92 (18)
C1—C2—C3—C4	−0.2 (3)	N2—C9—C10—C11	11.6 (3)
C2—C3—C4—C5	−1.0 (3)	C8—C9—C10—C11	−170.55 (19)
C2—C3—C4—C7	−178.1 (2)	N2—C9—C10—C15	−167.37 (19)
C3—C4—C5—C6	1.5 (3)	C8—C9—C10—C15	10.5 (3)
C7—C4—C5—C6	178.58 (19)	C15—C10—C11—C12	1.4 (3)
C2—C1—C6—C5	−0.4 (3)	C9—C10—C11—C12	−177.6 (2)
F1—C1—C6—C5	178.42 (19)	C10—C11—C12—C13	0.9 (4)
C4—C5—C6—C1	−0.8 (3)	C11—C12—C13—C14	−2.7 (4)
C17—N1—C7—C4	−79.3 (2)	C11—C12—C13—C16	176.3 (2)
N2—N1—C7—C4	104.12 (18)	C12—C13—C14—C15	2.3 (3)
C17—N1—C7—C8	160.42 (18)	C16—C13—C14—C15	−176.7 (2)
N2—N1—C7—C8	−16.1 (2)	C13—C14—C15—C10	−0.1 (3)
C5—C4—C7—N1	149.56 (18)	C11—C10—C15—C14	−1.8 (3)
C3—C4—C7—N1	−33.4 (2)	C9—C10—C15—C14	177.28 (19)
C5—C4—C7—C8	−98.2 (2)	N2—N1—C17—N3	1.2 (3)
C3—C4—C7—C8	78.8 (2)	C7—N1—C17—N3	−175.12 (18)
N1—C7—C8—C9	15.56 (19)	N2—N1—C17—S1	−179.70 (14)
C4—C7—C8—C9	−103.26 (18)	C7—N1—C17—S1	4.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H31···N2	0.88	2.23	2.611 (3)	106
N3—H31···F1ⁱ	0.88	2.41	3.255 (2)	162
N3—H32···S1ⁱⁱ	0.88	2.83	3.538 (2)	138
C16—H16B···F1ⁱⁱⁱ	0.96	2.55	3.478 (3)	163

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆FN₃S
M_r	313.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	14.4154 (10), 11.3197 (9), 9.5575 (8)
β (°)	103.991 (8)
V (Å³)	1513.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.30 × 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	0.772, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9303, 3500, 2370
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.122, 1.04
No. of reflections	3500
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.26

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

D—H···A	D—H	H···A	D···A	D—H···A
N3—H31···N2	0.88	2.23	2.611 (3)	106
N3—H31···F1ⁱ	0.88	2.41	3.255 (2)	162
N3—H32···S1ⁱⁱ	0.88	2.83	3.538 (2)	138
C16—H16B···F1ⁱⁱⁱ	0.96	2.55	3.478 (3)	163

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

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
Chantrapromma, S., Nonthason, P., Suwunwong, T. & Fun, H.-K. (2012). Acta Cryst. E68, o830–o831. CSD CrossRef IUCr Journals 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
Nonthason, P., Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o3501–o3502. Web of Science CSD 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 3| March 2013| Pages o385-o386

doi:10.1107/S1600536813004194

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-di­hydro-1H-pyrazole-1-carbo­thio­amide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

5-(4-Fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide