4-[(2,4-Difluoro­phen­yl)hydrazinyl­idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothio­amide

Fun, H.-K.; Asik, S.I.J.; Razak, I.A.; Shetty, S.; Kalluraya, B.

doi:10.1107/S1600536811044576

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3116

doi:10.1107/S1600536811044576

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4-[(2,4-Difluorophenyl)hydrazinylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothioamide

Hoong-Kun Fun,^a ^*‡ Safra Izuani Jama Asik,^a Ibrahim Abdul Razak,^a Shobhitha Shetty ^b and Balakrishna Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 24 October 2011; accepted 25 October 2011; online 29 October 2011)

In the title compound, C₁₁H₉F₂N₅OS, the pyrazole ring forms a dihedral angle of 16.42 (6)° with the benzene ring. Intramolecular N—H⋯O hydrogen bonds generate two S(6) ring motifs. In the crystal, an R₂²(8) ring motif is formed by a pair of intermolecular N—H⋯S hydrogen bonds. Intermolecular C—H⋯F hydrogen bonds further link the molecules into a three-dimensional network.

Related literature

For the biological activity of pyrazole derivatives, see: Isloor et al. (2009 ); Rai et al. (2008 ); Bradbury & Pucci (2008 ); Girisha et al. (2010 ). For a related structure, see: Fun et al. (2011 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₁₁H₉F₂N₅OS
M_r = 297.29
Triclinic, $[P \overline 1]$
a = 7.9003 (1) Å
b = 8.2400 (1) Å
c = 10.1378 (1) Å
α = 103.409 (1)°
β = 99.864 (1)°
γ = 99.372 (1)°
V = 618.18 (1) Å³
Z = 2
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 100 K
0.41 × 0.23 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.890, T_max = 0.977
15661 measured reflections
4211 independent reflections
3546 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.091
S = 1.06
4211 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1	0.863 (17)	2.080 (17)	2.7605 (13)	135.2 (15)
N5—H1N5⋯S1ⁱ	0.842 (17)	2.607 (17)	3.4279 (11)	165.5 (15)
N5—H2N5⋯O1	0.880 (17)	2.048 (17)	2.7208 (13)	132.5 (14)
C10—H10A⋯F1ⁱⁱ	0.98	2.47	3.3016 (14)	143
C10—H10C⋯F1ⁱⁱⁱ	0.98	2.53	3.2775 (14)	133
C10—H10C⋯F2^iv	0.98	2.55	3.2145 (14)	125
Symmetry codes: (i) -x, -y, -z+1; (ii) x+1, y, z+1; (iii) -x, -y+2, -z; (iv) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811044576/is2796sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044576/is2796Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811044576/is2796Isup3.cml

checkCIF report

Comment top

The pyrazole ring is a prominent structural moiety found in numerous pharmaceutically active compounds. This is mainly due to the easy preparation and the important pharmacological activity. Therefore, the synthesis and selective functionalization of pyrazoles have been focus of active research area over the years (Isloor et al., 2009). Pyrazoles have been reported to possess antibacterial activity (Rai et al., 2008), and found to posses inhibitor activity against DNA gyrase and topoisomerase IV at their respective ATP-binding sites (Bradbury & Pucci, 2008). Moreover, pyrazole-containing compounds have received considerable attention owing to their diverse chemotherapeutic potentials including versatile anti-inflammatory and antimicrobial activities (Girisha et al., 2010). The synthetic route followed for obtaining the title compound (I) involves the diazotization of substituted anilines to give the diazonium salts followed by coupling with ethyl acetoacetate in the presence of sodium acetate to give the corresponding oxobutanoate which on further reaction with thiosemicarbazide in acetic acid gave the required thioamides.

In the title compound of (I), (Fig. 1), the pyrazole (N3/N4/C7–C9) ring is essentially planar, with a maximum deviation of 0.007 (1) Å for atom C9 and makes a dihedral angle of 16.42 (6)° with the benzene (C1–C6) ring. The intramolecular N1—H1N1···O1 and N5—H2N5···O1 hydrogen bonds generate two S(6) ring motifs (Bernstein et al., 1995). The geometric parameters are consistent to those observed in a closely related structure (Fun et al., 2011).

In the crystal structure, (Fig. 2), an R₂²(8) ring motif is formed by intermolecular N5—H1N5···S1 hydrogen bonds (Table 1). Intermolecular C10—H10A···F1, C10—H10C···F1 and C10—H10C···F2 (Table 1) hydrogen bonds further link the molecules into a three- dimensional network.

Related literature top

For the biological activity of pyrazole derivatives, see: Isloor et al. (2009); Rai et al. (2008); Bradbury & Pucci (2008); Girisha et al. (2010). For a related structure, see: Fun et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To a solution of ethyl-2-[(2,4-difluorophenyl)hydrazono]-3-oxobutanoate (0.01 mol) dissolved in glacial acetic acid (15 ml), a solution of thiosemicarbazide (0.02 mol) in glacial acetic acid (15 ml) was added and the mixture was refluxed for 4 h. It is cooled and allowed to stand overnight. The solid product that separated out was filtered and dried. It was then recrystallized from ethanol. Crystals suitable for X-ray analysis were obtained from 1:2 mixture of DMF and ethanol by slow evaporation.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal packing, viewed along the b-axis, showing the molecules formed a into three-dimensional network. Hydrogen atoms that not involved in hydrogen bonding (dashed lines) are omitted for clarity.

4-[(2,4-Difluorophenyl)hydrazinylidene]-3-methyl-5-oxo-4,5-dihydro- 1H-pyrazole-1-carbothioamide top

Crystal data top

C₁₁H₉F₂N₅OS	Z = 2
M_r = 297.29	F(000) = 304
Triclinic, P1	D_x = 1.597 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9003 (1) Å	Cell parameters from 7383 reflections
b = 8.2400 (1) Å	θ = 2.6–31.9°
c = 10.1378 (1) Å	µ = 0.29 mm⁻¹
α = 103.409 (1)°	T = 100 K
β = 99.864 (1)°	Block, green
γ = 99.372 (1)°	0.41 × 0.23 × 0.08 mm
V = 618.18 (1) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4211 independent reflections
Radiation source: fine-focus sealed tube	3546 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 31.9°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.890, T_max = 0.977	k = −12→12
15661 measured reflections	l = −15→15

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0469P)² + 0.1483P] where P = (F_o² + 2F_c²)/3
4211 reflections	(Δ/σ)_max = 0.001
194 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₁H₉F₂N₅OS	γ = 99.372 (1)°
M_r = 297.29	V = 618.18 (1) Å³
Triclinic, P1	Z = 2
a = 7.9003 (1) Å	Mo Kα radiation
b = 8.2400 (1) Å	µ = 0.29 mm⁻¹
c = 10.1378 (1) Å	T = 100 K
α = 103.409 (1)°	0.41 × 0.23 × 0.08 mm
β = 99.864 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4211 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3546 reflections with I > 2σ(I)
T_min = 0.890, T_max = 0.977	R_int = 0.024
15661 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.46 e Å⁻³
4211 reflections	Δρ_min = −0.27 e Å⁻³
194 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.21061 (4)	0.24608 (3)	0.56219 (3)	0.01893 (8)
F1	−0.53111 (10)	0.91062 (10)	−0.26133 (8)	0.02844 (17)
F2	−0.43017 (9)	0.41257 (8)	−0.13817 (7)	0.02208 (15)
O1	−0.14398 (10)	0.30354 (10)	0.16468 (8)	0.01952 (16)
N1	−0.15277 (12)	0.58736 (12)	0.06501 (10)	0.01746 (17)
N2	−0.00803 (12)	0.66676 (12)	0.15852 (9)	0.01665 (17)
N3	0.08671 (12)	0.38926 (11)	0.36455 (9)	0.01611 (17)
N4	0.22017 (12)	0.53670 (11)	0.43282 (10)	0.01660 (17)
N5	−0.06153 (13)	0.11880 (12)	0.34770 (11)	0.02077 (19)
C1	−0.19357 (15)	0.85108 (14)	0.00178 (12)	0.0202 (2)
H1A	−0.0949	0.9165	0.0722	0.024*
C2	−0.29073 (16)	0.93080 (15)	−0.08133 (13)	0.0229 (2)
H2A	−0.2603	1.0507	−0.0681	0.027*
C3	−0.43254 (15)	0.83195 (15)	−0.18365 (12)	0.0208 (2)
C4	−0.48169 (14)	0.65643 (14)	−0.21030 (12)	0.0190 (2)
H4A	−0.5768	0.5907	−0.2839	0.023*
C5	−0.38454 (14)	0.58275 (13)	−0.12371 (11)	0.01665 (19)
C6	−0.24060 (14)	0.67551 (13)	−0.01797 (11)	0.01630 (19)
C7	−0.01793 (13)	0.40835 (13)	0.24639 (11)	0.01574 (19)
C8	0.05592 (13)	0.58088 (13)	0.24210 (11)	0.01541 (18)
C9	0.20256 (14)	0.64684 (13)	0.36007 (11)	0.01583 (19)
C10	0.32130 (15)	0.81794 (13)	0.39924 (12)	0.0200 (2)
H10A	0.4110	0.8292	0.4825	0.030*
H10B	0.2529	0.9064	0.4184	0.030*
H10C	0.3783	0.8311	0.3227	0.030*
C11	0.07145 (14)	0.24765 (13)	0.41963 (11)	0.01608 (19)
H1N1	−0.198 (2)	0.482 (2)	0.0569 (18)	0.036 (5)*
H1N5	−0.078 (2)	0.032 (2)	0.3780 (19)	0.036 (4)*
H2N5	−0.138 (2)	0.126 (2)	0.2763 (18)	0.030 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01932 (13)	0.01622 (12)	0.01939 (14)	0.00185 (9)	−0.00104 (10)	0.00627 (10)
F1	0.0254 (4)	0.0287 (4)	0.0295 (4)	0.0030 (3)	−0.0064 (3)	0.0154 (3)
F2	0.0226 (3)	0.0156 (3)	0.0241 (3)	−0.0004 (2)	0.0008 (3)	0.0039 (3)
O1	0.0175 (4)	0.0184 (4)	0.0183 (4)	−0.0008 (3)	−0.0013 (3)	0.0032 (3)
N1	0.0172 (4)	0.0165 (4)	0.0164 (4)	0.0018 (3)	−0.0009 (3)	0.0044 (3)
N2	0.0170 (4)	0.0175 (4)	0.0143 (4)	0.0034 (3)	0.0018 (3)	0.0032 (3)
N3	0.0164 (4)	0.0135 (4)	0.0161 (4)	0.0005 (3)	−0.0002 (3)	0.0041 (3)
N4	0.0164 (4)	0.0134 (4)	0.0170 (4)	0.0000 (3)	0.0003 (3)	0.0027 (3)
N5	0.0211 (5)	0.0163 (4)	0.0216 (5)	−0.0015 (3)	−0.0015 (4)	0.0068 (4)
C1	0.0194 (5)	0.0186 (5)	0.0185 (5)	0.0011 (4)	−0.0028 (4)	0.0038 (4)
C2	0.0238 (5)	0.0183 (5)	0.0236 (6)	0.0020 (4)	−0.0022 (4)	0.0067 (4)
C3	0.0195 (5)	0.0231 (5)	0.0193 (5)	0.0038 (4)	−0.0010 (4)	0.0089 (4)
C4	0.0159 (5)	0.0220 (5)	0.0164 (5)	0.0005 (4)	0.0002 (4)	0.0046 (4)
C5	0.0166 (5)	0.0160 (4)	0.0157 (5)	0.0009 (4)	0.0030 (4)	0.0031 (4)
C6	0.0165 (4)	0.0176 (4)	0.0146 (4)	0.0036 (4)	0.0023 (4)	0.0046 (4)
C7	0.0152 (4)	0.0163 (4)	0.0147 (4)	0.0028 (3)	0.0022 (4)	0.0033 (4)
C8	0.0156 (4)	0.0146 (4)	0.0146 (4)	0.0018 (3)	0.0018 (4)	0.0030 (4)
C9	0.0164 (4)	0.0146 (4)	0.0152 (4)	0.0025 (3)	0.0022 (4)	0.0030 (4)
C10	0.0219 (5)	0.0148 (4)	0.0197 (5)	−0.0006 (4)	0.0005 (4)	0.0037 (4)
C11	0.0164 (4)	0.0143 (4)	0.0170 (5)	0.0030 (3)	0.0029 (4)	0.0041 (4)

Geometric parameters (Å, º) top

S1—C11	1.6633 (11)	C1—C2	1.3893 (15)
F1—C3	1.3557 (12)	C1—C6	1.3914 (15)
F2—C5	1.3564 (12)	C1—H1A	0.9500
O1—C7	1.2366 (13)	C2—C3	1.3810 (16)
N1—N2	1.3159 (13)	C2—H2A	0.9500
N1—C6	1.4016 (13)	C3—C4	1.3840 (16)
N1—H1N1	0.866 (17)	C4—C5	1.3772 (15)
N2—C8	1.3122 (13)	C4—H4A	0.9500
N3—C7	1.3905 (13)	C5—C6	1.3949 (15)
N3—C11	1.4026 (13)	C7—C8	1.4597 (14)
N3—N4	1.4176 (12)	C8—C9	1.4445 (14)
N4—C9	1.3051 (13)	C9—C10	1.4858 (14)
N5—C11	1.3334 (14)	C10—H10A	0.9800
N5—H1N5	0.840 (18)	C10—H10B	0.9800
N5—H2N5	0.878 (17)	C10—H10C	0.9800

N2—N1—C6	120.34 (9)	F2—C5—C6	117.21 (9)
N2—N1—H1N1	120.6 (12)	C4—C5—C6	123.13 (10)
C6—N1—H1N1	119.0 (12)	C1—C6—C5	118.51 (10)
C8—N2—N1	116.66 (9)	C1—C6—N1	123.27 (10)
C7—N3—C11	127.86 (9)	C5—C6—N1	118.20 (9)
C7—N3—N4	112.25 (8)	O1—C7—N3	127.95 (10)
C11—N3—N4	119.89 (9)	O1—C7—C8	128.37 (10)
C9—N4—N3	106.61 (8)	N3—C7—C8	103.68 (9)
C11—N5—H1N5	117.8 (12)	N2—C8—C9	126.25 (9)
C11—N5—H2N5	122.4 (11)	N2—C8—C7	127.47 (10)
H1N5—N5—H2N5	119.5 (16)	C9—C8—C7	105.88 (9)
C2—C1—C6	120.11 (10)	N4—C9—C8	111.56 (9)
C2—C1—H1A	119.9	N4—C9—C10	122.26 (10)
C6—C1—H1A	119.9	C8—C9—C10	126.18 (9)
C3—C2—C1	118.57 (10)	C9—C10—H10A	109.5
C3—C2—H2A	120.7	C9—C10—H10B	109.5
C1—C2—H2A	120.7	H10A—C10—H10B	109.5
F1—C3—C2	118.52 (10)	C9—C10—H10C	109.5
F1—C3—C4	117.86 (10)	H10A—C10—H10C	109.5
C2—C3—C4	123.62 (10)	H10B—C10—H10C	109.5
C5—C4—C3	116.00 (10)	N5—C11—N3	114.10 (9)
C5—C4—H4A	122.0	N5—C11—S1	124.50 (8)
C3—C4—H4A	122.0	N3—C11—S1	121.40 (8)
F2—C5—C4	119.65 (10)

C6—N1—N2—C8	172.87 (9)	N4—N3—C7—O1	179.75 (10)
C7—N3—N4—C9	−0.44 (12)	C11—N3—C7—C8	178.66 (10)
C11—N3—N4—C9	−179.57 (9)	N4—N3—C7—C8	−0.38 (11)
C6—C1—C2—C3	−0.58 (18)	N1—N2—C8—C9	−173.72 (10)
C1—C2—C3—F1	177.63 (10)	N1—N2—C8—C7	−2.03 (16)
C1—C2—C3—C4	−1.39 (19)	O1—C7—C8—N2	7.81 (18)
F1—C3—C4—C5	−176.26 (10)	N3—C7—C8—N2	−172.05 (10)
C2—C3—C4—C5	2.77 (17)	O1—C7—C8—C9	−179.15 (10)
C3—C4—C5—F2	176.48 (10)	N3—C7—C8—C9	0.98 (11)
C3—C4—C5—C6	−2.30 (16)	N3—N4—C9—C8	1.11 (12)
C2—C1—C6—C5	1.00 (17)	N3—N4—C9—C10	−179.47 (9)
C2—C1—C6—N1	−177.62 (10)	N2—C8—C9—N4	171.79 (10)
F2—C5—C6—C1	−178.30 (10)	C7—C8—C9—N4	−1.35 (12)
C4—C5—C6—C1	0.50 (16)	N2—C8—C9—C10	−7.61 (17)
F2—C5—C6—N1	0.39 (14)	C7—C8—C9—C10	179.24 (10)
C4—C5—C6—N1	179.20 (10)	C7—N3—C11—N5	−0.44 (16)
N2—N1—C6—C1	−6.89 (16)	N4—N3—C11—N5	178.53 (9)
N2—N1—C6—C5	174.49 (9)	C7—N3—C11—S1	179.35 (8)
C11—N3—C7—O1	−1.21 (18)	N4—N3—C11—S1	−1.67 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	0.863 (17)	2.080 (17)	2.7605 (13)	135.2 (15)
N5—H1N5···S1ⁱ	0.842 (17)	2.607 (17)	3.4279 (11)	165.5 (15)
N5—H2N5···O1	0.880 (17)	2.048 (17)	2.7208 (13)	132.5 (14)
C10—H10A···F1ⁱⁱ	0.98	2.47	3.3016 (14)	143
C10—H10C···F1ⁱⁱⁱ	0.98	2.53	3.2775 (14)	133
C10—H10C···F2^iv	0.98	2.55	3.2145 (14)	125

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

Experimental details

Crystal data
Chemical formula	C₁₁H₉F₂N₅OS
M_r	297.29
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.9003 (1), 8.2400 (1), 10.1378 (1)
α, β, γ (°)	103.409 (1), 99.864 (1), 99.372 (1)
V (Å³)	618.18 (1)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.41 × 0.23 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.890, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	15661, 4211, 3546
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.743

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.091, 1.06
No. of reflections	4211
No. of parameters	194
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.27

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	0.863 (17)	2.080 (17)	2.7605 (13)	135.2 (15)
N5—H1N5···S1ⁱ	0.842 (17)	2.607 (17)	3.4279 (11)	165.5 (15)
N5—H2N5···O1	0.880 (17)	2.048 (17)	2.7208 (13)	132.5 (14)
C10—H10A···F1ⁱⁱ	0.9800	2.4700	3.3016 (14)	143.00
C10—H10C···F1ⁱⁱⁱ	0.9800	2.5300	3.2775 (14)	133.00
C10—H10C···F2^iv	0.9800	2.5500	3.2145 (14)	125.00

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF, IAR and SIJA thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grants (Nos.1001/PFIZIK/811160 and 1001/PFIZIK/ 811151).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bradbury, B. J. & Pucci, M. J. (2008). Curr. Opin. Pharmacol. 8, 574–581. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Volume 67| Part 11| November 2011| Page o3116

doi:10.1107/S1600536811044576

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

4-[(2,4-Di­fluoro­phen­yl)hydrazinyl­­idene]-3-methyl-5-oxo-4,5-di­hydro-1H-pyrazole-1-carbo­thio­amide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-[(2,4-Difluorophenyl)hydrazinylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothioamide