3-Methyl-5-oxo-4-(2-phenyl­hydrazinyl­idene)-4,5-dihydro-1H-pyrazole-1-carbothio­amide

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

doi:10.1107/S1600536811009779

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o928

doi:10.1107/S1600536811009779

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3-Methyl-5-oxo-4-(2-phenylhydrazinylidene)-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 14 March 2011; accepted 15 March 2011; online 19 March 2011)

In the title compound, C₁₁H₁₁N₅OS, the pyrazole ring is approximately planar, with a maximum deviation of 0.010 (2) Å. The dihedral angles between the benzene ring and the pyrazole and carbothioamide groups are 5.42 (9) and 10.61 (18)°, respectively. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are connected by intermolecular N—H⋯O and C—H⋯S hydrogen bonds, forming R₂²(12) ring motifs. In addition, there is a π–π stacking interaction [centroid–centroid distance = 3.5188 (11) Å] between the pyrazole and benzene rings. These interactions link the molecules into infinite chains along [001].

Related literature

For general background to and applications of pyrazole derivatives, see: Rai & Kalluraya (2006 ); Rai et al. (2008 ); Sridhar & Perumal (2003 ). For graph-set theory, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₁N₅OS
M_r = 261.31
Monoclinic, P 2₁ /c
a = 7.7388 (1) Å
b = 16.1103 (3) Å
c = 11.3575 (2) Å
β = 121.058 (1)°
V = 1213.00 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.53 × 0.39 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.874, T_max = 0.967
16258 measured reflections
4393 independent reflections
3037 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.135
S = 1.05
4393 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1	0.86	2.16	2.8147 (16)	132
N5—H5C⋯O1ⁱ	0.86	2.03	2.8806 (15)	172
C1—H1A⋯S1ⁱⁱ	0.93	2.80	3.6838 (16)	159
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536811009779/sj5118sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009779/sj5118Isup2.hkl

checkCIF report

Comment top

Pyrazole derivatives are in general well-known nitrogen-containing heterocyclic compounds and various procedures have been developed for their synthesis (Rai & Kalluraya, 2006). The chemistry of pyrazole derivatives has been the subject of much interest due to their importance for various applications and their widespread potential and proven biological and pharmacological activities (Rai et al., 2008). Steroids containing a pyrazole moiety are of interest as psychopharmacological agents. Some alkyl- and aryl-substituted pyrazoles have a sharply pronounced sedative action on the central nervous system. Furthermore, certain alkyl pyrazoles show significant bacteriostatic, bacteriocidal, fungicidal, analgesic and anti-pyretic activities (Sridhar & Perumal, 2003).

Fig.1 shows the molecular structure of (I). The pyrazole (C7–C9/N3/N4) ring is approximately planar with a maximum deviation of 0.010 (2) Å for atom C8. The dihedral angle between benzene and pyrazole rings is 5.42 (9)°. The carbothioamide group (S1/C11/N5) is twisted at a dihedral angle 10.61 (18)° from the pyrazole ring. The bond lengths (Allen et al., 1987) in (I) show normal values. An intramolecular N1—H1B···O1 hydrogen bond (Table 1) generates an S(6) ring motif (Bernstein et al., 1995).

In the crystal packing of (I) (Fig. 2), molecules are connected by N5—H5C···O1 and C1—H1A···S1 intermolecular hydrogen bonds to form R²₂(12) ring motifs. These interactions also link the molecules into infinite one-dimensional chains along [0 0 1]. In addition, there is a π–π stacking interaction between pyrazole (C7–C9/N3/N4; centroid Cg1) and benzene (C1–C6; centroid Cg2) rings with a Cg1···Cg2 separation of 3.5188 (11) Å.

Related literature top

For general background to and applications of pyrazole derivatives, see: Rai & Kalluraya (2006); Rai et al. (2008); Sridhar & Perumal (2003). For graph-set theory, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987).

Experimental top

To a solution of ethyl-3-oxo-2-(2-phenylhydrazinylidene) butanoate (0.01mol) dissolved in glacial acetic acid (20ml), a solution of thiosemicarbazide (0.02mol) in glacial acetic acid (25ml) 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 mixtures 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 (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of (I) viewed along the a axis, showing infinite one-dimensional chains along [0 0 1]. Hydrogen bonds are shown as dashed lines.

3-Methyl-5-oxo-4-(2-phenylhydrazinylidene)-4,5-dihydro-1H-pyrazole-1- carbothioamide top

Crystal data top

C₁₁H₁₁N₅OS	F(000) = 544
M_r = 261.31	D_x = 1.431 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5770 reflections
a = 7.7388 (1) Å	θ = 2.5–31.9°
b = 16.1103 (3) Å	µ = 0.26 mm⁻¹
c = 11.3575 (2) Å	T = 296 K
β = 121.058 (1)°	Plate, orange
V = 1213.00 (3) Å³	0.53 × 0.39 × 0.13 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4393 independent reflections
Radiation source: sealed tube	3037 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 32.6°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.874, T_max = 0.967	k = −24→23
16258 measured reflections	l = −17→16

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0587P)² + 0.2537P] where P = (F_o² + 2F_c²)/3
4393 reflections	(Δ/σ)_max < 0.001
164 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₁H₁₁N₅OS	V = 1213.00 (3) Å³
M_r = 261.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7388 (1) Å	µ = 0.26 mm⁻¹
b = 16.1103 (3) Å	T = 296 K
c = 11.3575 (2) Å	0.53 × 0.39 × 0.13 mm
β = 121.058 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4393 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3037 reflections with I > 2σ(I)
T_min = 0.874, T_max = 0.967	R_int = 0.026
16258 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.05	Δρ_max = 0.33 e Å⁻³
4393 reflections	Δρ_min = −0.39 e Å⁻³
164 parameters

Special details top

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	0.35472 (10)	0.29034 (2)	0.30227 (5)	0.07026 (19)
O1	0.36818 (17)	0.14963 (6)	0.49606 (10)	0.0434 (2)
N1	0.26541 (17)	0.00165 (7)	0.57723 (11)	0.0346 (2)
H1B	0.3036	0.0523	0.5989	0.041*
N2	0.23279 (17)	−0.02868 (7)	0.46071 (11)	0.0340 (2)
N3	0.25183 (18)	0.05536 (7)	0.18342 (11)	0.0340 (2)
N4	0.30783 (17)	0.12552 (6)	0.27173 (11)	0.0324 (2)
N5	0.3303 (2)	0.19488 (8)	0.10601 (13)	0.0478 (3)
H5B	0.3161	0.1470	0.0685	0.057*
H5C	0.3439	0.2384	0.0678	0.057*
C1	0.2876 (2)	−0.01706 (10)	0.79423 (14)	0.0413 (3)
H1A	0.3376	0.0367	0.8182	0.050*
C2	0.2625 (3)	−0.06542 (11)	0.88499 (15)	0.0494 (4)
H2A	0.2961	−0.0441	0.9703	0.059*
C3	0.1883 (3)	−0.14496 (11)	0.84978 (17)	0.0509 (4)
H3A	0.1732	−0.1775	0.9115	0.061*
C4	0.1363 (3)	−0.17618 (10)	0.72246 (19)	0.0523 (4)
H4A	0.0839	−0.2296	0.6983	0.063*
C5	0.1611 (2)	−0.12903 (9)	0.62989 (16)	0.0433 (3)
H5A	0.1272	−0.1505	0.5446	0.052*
C6	0.23757 (19)	−0.04923 (8)	0.66727 (13)	0.0337 (3)
C7	0.25637 (19)	0.01943 (7)	0.37735 (12)	0.0308 (2)
C8	0.31689 (19)	0.10634 (8)	0.39492 (12)	0.0313 (3)
C9	0.2218 (2)	−0.00556 (8)	0.24546 (13)	0.0328 (3)
C10	0.1592 (3)	−0.08981 (9)	0.18412 (16)	0.0481 (4)
H10A	0.0995	−0.0862	0.0863	0.072*
H10B	0.0625	−0.1121	0.2046	0.072*
H10C	0.2751	−0.1255	0.2219	0.072*
C11	0.3313 (2)	0.20147 (8)	0.22208 (14)	0.0356 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.1363 (5)	0.0316 (2)	0.0759 (3)	−0.0167 (2)	0.0783 (4)	−0.01097 (18)
O1	0.0638 (7)	0.0371 (5)	0.0345 (5)	−0.0008 (4)	0.0291 (5)	−0.0053 (4)
N1	0.0439 (6)	0.0335 (5)	0.0316 (5)	0.0008 (4)	0.0233 (5)	0.0044 (4)
N2	0.0390 (6)	0.0347 (5)	0.0320 (5)	0.0033 (4)	0.0210 (5)	0.0043 (4)
N3	0.0454 (6)	0.0316 (5)	0.0304 (5)	−0.0027 (4)	0.0233 (5)	−0.0037 (4)
N4	0.0459 (6)	0.0276 (5)	0.0302 (5)	−0.0019 (4)	0.0242 (5)	−0.0015 (4)
N5	0.0785 (10)	0.0355 (6)	0.0431 (6)	−0.0039 (6)	0.0411 (7)	0.0037 (5)
C1	0.0478 (8)	0.0442 (7)	0.0362 (6)	−0.0027 (6)	0.0247 (6)	0.0024 (6)
C2	0.0543 (9)	0.0645 (10)	0.0351 (7)	0.0010 (7)	0.0271 (7)	0.0084 (7)
C3	0.0547 (9)	0.0569 (9)	0.0507 (8)	0.0075 (7)	0.0339 (7)	0.0219 (7)
C4	0.0645 (10)	0.0377 (7)	0.0662 (10)	0.0024 (7)	0.0420 (9)	0.0121 (7)
C5	0.0561 (9)	0.0370 (7)	0.0448 (8)	0.0019 (6)	0.0318 (7)	0.0042 (6)
C6	0.0345 (6)	0.0375 (6)	0.0330 (6)	0.0050 (5)	0.0202 (5)	0.0091 (5)
C7	0.0368 (6)	0.0298 (5)	0.0298 (5)	0.0014 (5)	0.0201 (5)	0.0018 (4)
C8	0.0381 (6)	0.0309 (5)	0.0297 (5)	0.0024 (5)	0.0208 (5)	0.0004 (4)
C9	0.0397 (7)	0.0310 (6)	0.0314 (6)	−0.0003 (5)	0.0210 (5)	−0.0015 (4)
C10	0.0700 (10)	0.0342 (7)	0.0471 (8)	−0.0090 (6)	0.0351 (8)	−0.0083 (6)
C11	0.0441 (7)	0.0307 (6)	0.0377 (6)	−0.0003 (5)	0.0252 (6)	0.0024 (5)

Geometric parameters (Å, º) top

S1—C11	1.6560 (13)	C1—H1A	0.9300
O1—C8	1.2218 (15)	C2—C3	1.377 (3)
N1—N2	1.3073 (15)	C2—H2A	0.9300
N1—C6	1.4111 (16)	C3—C4	1.380 (3)
N1—H1B	0.8600	C3—H3A	0.9300
N2—C7	1.3072 (16)	C4—C5	1.389 (2)
N3—C9	1.2972 (17)	C4—H4A	0.9300
N3—N4	1.4222 (14)	C5—C6	1.387 (2)
N4—C11	1.3979 (16)	C5—H5A	0.9300
N4—C8	1.3988 (16)	C7—C9	1.4366 (17)
N5—C11	1.3185 (18)	C7—C8	1.4572 (17)
N5—H5B	0.8602	C9—C10	1.4880 (19)
N5—H5C	0.8600	C10—H10A	0.9600
C1—C2	1.383 (2)	C10—H10B	0.9600
C1—C6	1.3863 (19)	C10—H10C	0.9600

N2—N1—C6	119.64 (11)	C6—C5—H5A	120.7
N2—N1—H1B	120.2	C4—C5—H5A	120.7
C6—N1—H1B	120.2	C1—C6—C5	120.73 (13)
C7—N2—N1	119.04 (11)	C1—C6—N1	118.13 (12)
C9—N3—N4	107.04 (10)	C5—C6—N1	121.13 (12)
C11—N4—C8	130.31 (11)	N2—C7—C9	124.65 (12)
C11—N4—N3	117.83 (10)	N2—C7—C8	128.73 (12)
C8—N4—N3	111.70 (10)	C9—C7—C8	106.61 (10)
C11—N5—H5B	120.0	O1—C8—N4	129.69 (12)
C11—N5—H5C	120.0	O1—C8—C7	127.07 (12)
H5B—N5—H5C	120.0	N4—C8—C7	103.20 (10)
C2—C1—C6	119.56 (14)	N3—C9—C7	111.42 (11)
C2—C1—H1A	120.2	N3—C9—C10	122.83 (12)
C6—C1—H1A	120.2	C7—C9—C10	125.75 (12)
C3—C2—C1	120.38 (15)	C9—C10—H10A	109.5
C3—C2—H2A	119.8	C9—C10—H10B	109.5
C1—C2—H2A	119.8	H10A—C10—H10B	109.5
C2—C3—C4	119.73 (14)	C9—C10—H10C	109.5
C2—C3—H3A	120.1	H10A—C10—H10C	109.5
C4—C3—H3A	120.1	H10B—C10—H10C	109.5
C3—C4—C5	120.96 (16)	N5—C11—N4	113.45 (11)
C3—C4—H4A	119.5	N5—C11—S1	124.20 (10)
C5—C4—H4A	119.5	N4—C11—S1	122.34 (10)
C6—C5—C4	118.63 (15)

C6—N1—N2—C7	179.04 (11)	C11—N4—C8—C7	173.49 (13)
C9—N3—N4—C11	−174.52 (12)	N3—N4—C8—C7	−1.73 (14)
C9—N3—N4—C8	1.36 (15)	N2—C7—C8—O1	4.4 (2)
C6—C1—C2—C3	−0.1 (2)	C9—C7—C8—O1	−176.61 (13)
C1—C2—C3—C4	−0.8 (3)	N2—C7—C8—N4	−177.54 (13)
C2—C3—C4—C5	1.2 (3)	C9—C7—C8—N4	1.46 (13)
C3—C4—C5—C6	−0.7 (2)	N4—N3—C9—C7	−0.33 (15)
C2—C1—C6—C5	0.6 (2)	N4—N3—C9—C10	179.58 (13)
C2—C1—C6—N1	−179.84 (13)	N2—C7—C9—N3	178.31 (12)
C4—C5—C6—C1	−0.2 (2)	C8—C7—C9—N3	−0.73 (15)
C4—C5—C6—N1	−179.78 (13)	N2—C7—C9—C10	−1.6 (2)
N2—N1—C6—C1	175.36 (12)	C8—C7—C9—C10	179.36 (14)
N2—N1—C6—C5	−5.05 (19)	C8—N4—C11—N5	174.38 (13)
N1—N2—C7—C9	−178.74 (12)	N3—N4—C11—N5	−10.64 (18)
N1—N2—C7—C8	0.1 (2)	C8—N4—C11—S1	−6.4 (2)
C11—N4—C8—O1	−8.5 (2)	N3—N4—C11—S1	168.56 (10)
N3—N4—C8—O1	176.27 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1	0.86	2.16	2.8147 (16)	132
N5—H5C···O1ⁱ	0.86	2.03	2.8806 (15)	172
C1—H1A···S1ⁱⁱ	0.93	2.80	3.6838 (16)	159

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁N₅OS
M_r	261.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.7388 (1), 16.1103 (3), 11.3575 (2)
β (°)	121.058 (1)
V (Å³)	1213.00 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.53 × 0.39 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.874, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	16258, 4393, 3037
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.135, 1.05
No. of reflections	4393
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.39

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—H1B···O1	0.86	2.16	2.8147 (16)	132
N5—H5C···O1ⁱ	0.86	2.03	2.8806 (15)	172
C1—H1A···S1ⁱⁱ	0.93	2.80	3.6838 (16)	159

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

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

References

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Volume 67| Part 4| April 2011| Page o928

doi:10.1107/S1600536811009779

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

3-Methyl-5-oxo-4-(2-phenyl­hydrazinyl­­idene)-4,5-di­hydro-1H-pyrazole-1-carbo­thio­amide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

3-Methyl-5-oxo-4-(2-phenylhydrazinylidene)-4,5-dihydro-1H-pyrazole-1-carbothioamide