4-[2-(4-Chloro-phen-yl)hydrazinyl-idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothio-amide.

In the title mol-ecule, C(11)H(10)ClN(5)OS, an intra-molecular N-H⋯O hydrogen forms an S(6) ring motif. The dihedral angle between the pyrazole ring and the benzene ring is 3.77 (8)°. In the crystal, mol-ecules are linked by N-H⋯S and N-H⋯O hydrogen bonds into layers parallel to the bc plane.

Related literature

For the biological activity and pharmacological properties of pyrazole derivatives, see: Rai et al. (2008 ▶); Girisha et al. (2010 ▶); Isloor et al. (2009 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H10ClN5OS

M = 295.75

Monoclinic,

a = 25.0899 (17) Å

b = 11.6075 (9) Å

c = 9.0806 (6) Å

β = 99.516 (1)°

V = 2608.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.45 mm−1

T = 296 K

0.48 × 0.33 × 0.17 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.812, T max = 0.927

22139 measured reflections

3827 independent reflections

3125 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.120

S = 1.04

3827 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.49 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811038463/lh5337sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038463/lh5337Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811038463/lh5337Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H10ClN5OS	F(000) = 1216
Mr = 295.75	Dx = 1.506 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9651 reflections
a = 25.0899 (17) Å	θ = 2.9–29.9°
b = 11.6075 (9) Å	µ = 0.45 mm−1
c = 9.0806 (6) Å	T = 296 K
β = 99.516 (1)°	Block, orange
V = 2608.2 (3) Å3	0.48 × 0.33 × 0.17 mm
Z = 8

Bruker SMART APEXII DUO CCD area-detector diffractometer	3827 independent reflections
Radiation source: fine-focus sealed tube	3125 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 30.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −35→35
Tmin = 0.812, Tmax = 0.927	k = −16→16
22139 measured reflections	l = −12→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0678P)2 + 1.0988P] where P = (Fo2 + 2Fc2)/3
3827 reflections	(Δ/σ)max = 0.003
185 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.247690 (16)	0.67094 (3)	0.16327 (4)	0.04930 (13)
Cl1	0.47498 (2)	1.36700 (4)	0.93948 (6)	0.07500 (18)
O1	0.29887 (5)	0.85770 (9)	0.39231 (11)	0.0481 (3)
N1	0.30587 (5)	0.65709 (9)	0.43842 (11)	0.0376 (2)
N2	0.33273 (5)	0.58737 (10)	0.55643 (12)	0.0456 (3)
N3	0.37848 (5)	0.86126 (10)	0.67837 (13)	0.0431 (3)
N4	0.36803 (5)	0.96471 (10)	0.62440 (13)	0.0424 (3)
N5	0.26388 (6)	0.49214 (11)	0.34633 (13)	0.0489 (3)
C1	0.35437 (5)	0.77370 (11)	0.60545 (14)	0.0397 (3)
C2	0.31655 (5)	0.77385 (11)	0.46481 (13)	0.0358 (2)
C3	0.36083 (7)	0.65570 (12)	0.65135 (16)	0.0471 (3)
C4	0.39475 (5)	1.05982 (11)	0.69841 (14)	0.0389 (3)
C5	0.43223 (6)	1.04497 (13)	0.82750 (17)	0.0504 (3)
H5A	0.4408	0.9714	0.8647	0.060*
C6	0.45677 (7)	1.14060 (14)	0.90042 (19)	0.0557 (4)
H6A	0.4818	1.1317	0.9875	0.067*
C7	0.44409 (6)	1.24900 (13)	0.84375 (17)	0.0479 (3)
C8	0.40700 (6)	1.26442 (13)	0.71486 (17)	0.0510 (3)
H8A	0.3988	1.3380	0.6774	0.061*
C9	0.38221 (6)	1.16883 (12)	0.64217 (17)	0.0473 (3)
H9A	0.3571	1.1780	0.5554	0.057*
C10	0.27250 (5)	0.60195 (11)	0.32065 (13)	0.0374 (3)
C11	0.39486 (10)	0.61297 (16)	0.7902 (2)	0.0773 (6)
H11A	0.3845	0.5356	0.8097	0.116*
H11B	0.3899	0.6616	0.8724	0.116*
H11C	0.4322	0.6141	0.7782	0.116*
H1N4	0.3454 (7)	0.9766 (17)	0.536 (2)	0.052 (5)*
H1N5	0.2758 (8)	0.4615 (18)	0.435 (2)	0.060 (5)*
H2N5	0.2431 (8)	0.4515 (19)	0.272 (2)	0.064 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0633 (2)	0.0481 (2)	0.03108 (17)	0.00100 (15)	−0.00811 (14)	0.00135 (12)
Cl1	0.0730 (3)	0.0509 (2)	0.0885 (4)	−0.00312 (19)	−0.0239 (2)	−0.0250 (2)
O1	0.0625 (6)	0.0356 (5)	0.0409 (5)	0.0050 (4)	−0.0071 (4)	0.0029 (4)
N1	0.0460 (6)	0.0343 (5)	0.0287 (5)	−0.0019 (4)	−0.0046 (4)	0.0015 (4)
N2	0.0584 (7)	0.0352 (5)	0.0371 (5)	−0.0016 (5)	−0.0104 (5)	0.0047 (4)
N3	0.0486 (6)	0.0387 (5)	0.0392 (5)	−0.0032 (5)	−0.0011 (5)	−0.0034 (4)
N4	0.0485 (6)	0.0366 (5)	0.0384 (5)	−0.0032 (4)	−0.0034 (5)	−0.0035 (4)
N5	0.0674 (8)	0.0416 (6)	0.0326 (5)	−0.0111 (6)	−0.0067 (5)	−0.0016 (5)
C1	0.0455 (7)	0.0359 (6)	0.0343 (5)	−0.0020 (5)	−0.0035 (5)	−0.0011 (5)
C2	0.0411 (6)	0.0342 (6)	0.0306 (5)	0.0010 (5)	0.0019 (4)	−0.0003 (4)
C3	0.0566 (8)	0.0391 (6)	0.0389 (6)	−0.0021 (6)	−0.0118 (6)	0.0031 (5)
C4	0.0398 (6)	0.0382 (6)	0.0374 (6)	−0.0020 (5)	0.0020 (5)	−0.0059 (5)
C5	0.0521 (8)	0.0413 (7)	0.0515 (8)	0.0038 (6)	−0.0099 (6)	−0.0034 (6)
C6	0.0529 (8)	0.0523 (8)	0.0531 (8)	0.0040 (7)	−0.0175 (7)	−0.0083 (7)
C7	0.0438 (7)	0.0429 (7)	0.0529 (7)	−0.0011 (5)	−0.0037 (6)	−0.0127 (6)
C8	0.0552 (8)	0.0379 (7)	0.0547 (8)	−0.0012 (6)	−0.0060 (6)	−0.0025 (6)
C9	0.0518 (8)	0.0412 (7)	0.0431 (7)	−0.0022 (6)	−0.0087 (6)	−0.0011 (5)
C10	0.0414 (6)	0.0404 (6)	0.0286 (5)	−0.0022 (5)	0.0008 (4)	−0.0036 (4)
C11	0.1033 (15)	0.0516 (9)	0.0583 (10)	−0.0039 (9)	−0.0415 (10)	0.0100 (8)

S1—C10	1.6664 (13)	C1—C2	1.4597 (17)
Cl1—C7	1.7347 (14)	C3—C11	1.486 (2)
O1—C2	1.2169 (16)	C4—C9	1.3813 (19)
N1—C2	1.3945 (16)	C4—C5	1.3870 (19)
N1—C10	1.3995 (15)	C5—C6	1.384 (2)
N1—N2	1.4207 (15)	C5—H5A	0.9300
N2—C3	1.2916 (18)	C6—C7	1.377 (2)
N3—C1	1.3057 (17)	C6—H6A	0.9300
N3—N4	1.3070 (16)	C7—C8	1.381 (2)
N4—C4	1.4039 (16)	C8—C9	1.385 (2)
N4—H1N4	0.912 (18)	C8—H8A	0.9300
N5—C10	1.3200 (18)	C9—H9A	0.9300
N5—H1N5	0.89 (2)	C11—H11A	0.9600
N5—H2N5	0.91 (2)	C11—H11B	0.9600
C1—C3	1.4331 (19)	C11—H11C	0.9600
C2—N1—C10	130.50 (11)	C6—C5—H5A	120.3
C2—N1—N2	111.74 (10)	C4—C5—H5A	120.3
C10—N1—N2	117.72 (10)	C7—C6—C5	119.82 (14)
C3—N2—N1	106.99 (11)	C7—C6—H6A	120.1
C1—N3—N4	118.53 (12)	C5—C6—H6A	120.1
N3—N4—C4	119.51 (11)	C6—C7—C8	121.12 (13)
N3—N4—H1N4	121.7 (12)	C6—C7—Cl1	118.55 (11)
C4—N4—H1N4	118.7 (12)	C8—C7—Cl1	120.33 (12)
C10—N5—H1N5	120.4 (13)	C7—C8—C9	119.12 (14)
C10—N5—H2N5	117.2 (13)	C7—C8—H8A	120.4
H1N5—N5—H2N5	122.2 (19)	C9—C8—H8A	120.4
N3—C1—C3	125.15 (12)	C4—C9—C8	120.05 (13)
N3—C1—C2	128.49 (12)	C4—C9—H9A	120.0
C3—C1—C2	106.35 (11)	C8—C9—H9A	120.0
O1—C2—N1	129.93 (12)	N5—C10—N1	113.67 (11)
O1—C2—C1	126.90 (12)	N5—C10—S1	124.52 (10)
N1—C2—C1	103.17 (10)	N1—C10—S1	121.81 (10)
N2—C3—C1	111.70 (12)	C3—C11—H11A	109.5
N2—C3—C11	122.34 (14)	C3—C11—H11B	109.5
C1—C3—C11	125.96 (13)	H11A—C11—H11B	109.5
C9—C4—C5	120.50 (12)	C3—C11—H11C	109.5
C9—C4—N4	118.80 (12)	H11A—C11—H11C	109.5
C5—C4—N4	120.68 (12)	H11B—C11—H11C	109.5
C6—C5—C4	119.38 (14)
C2—N1—N2—C3	−2.16 (17)	C2—C1—C3—C11	−178.78 (18)
C10—N1—N2—C3	−179.95 (13)	N3—N4—C4—C9	−178.31 (14)
C1—N3—N4—C4	−178.03 (13)	N3—N4—C4—C5	0.3 (2)
N4—N3—C1—C3	−178.84 (15)	C9—C4—C5—C6	0.5 (2)
N4—N3—C1—C2	1.4 (2)	N4—C4—C5—C6	−178.13 (14)
C10—N1—C2—O1	1.0 (2)	C4—C5—C6—C7	−0.5 (3)
N2—N1—C2—O1	−176.43 (14)	C5—C6—C7—C8	0.2 (3)
C10—N1—C2—C1	179.99 (13)	C5—C6—C7—Cl1	179.16 (14)
N2—N1—C2—C1	2.57 (15)	C6—C7—C8—C9	0.1 (3)
N3—C1—C2—O1	−3.2 (2)	Cl1—C7—C8—C9	−178.82 (13)
C3—C1—C2—O1	177.00 (14)	C5—C4—C9—C8	−0.2 (2)
N3—C1—C2—N1	177.80 (14)	N4—C4—C9—C8	178.48 (14)
C3—C1—C2—N1	−2.04 (15)	C7—C8—C9—C4	−0.2 (3)
N1—N2—C3—C1	0.72 (19)	C2—N1—C10—N5	−167.44 (14)
N1—N2—C3—C11	−179.63 (18)	N2—N1—C10—N5	9.85 (18)
N3—C1—C3—N2	−178.98 (14)	C2—N1—C10—S1	13.6 (2)
C2—C1—C3—N2	0.86 (19)	N2—N1—C10—S1	−169.10 (10)
N3—C1—C3—C11	1.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···O1	0.914 (18)	2.114 (19)	2.7903 (16)	129.9 (16)
N5—H1N5···S1i	0.89 (2)	2.76 (2)	3.5239 (13)	144.5 (16)
N5—H2N5···O1ii	0.91 (2)	2.00 (2)	2.9124 (15)	177.0 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H1N4⋯O1	0.914 (18)	2.114 (19)	2.7903 (16)	129.9 (16)
N5—H1N5⋯S1i	0.89 (2)	2.76 (2)	3.5239 (13)	144.5 (16)
N5—H2N5⋯O1ii	0.91 (2)	2.00 (2)	2.9124 (15)	177.0 (19)

Symmetry codes: (i) ; (ii) .