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

In the title compound, C(11)H(10)BrN(5)OS, the approximately planar pyrazole ring [maximum deviation = 0.014 (2) Å] forms a dihedral angle of 5.49 (13)° with the benzene ring. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked through inter-molecular N-H⋯S and N-H⋯O hydrogen bonds, forming a two-dimensional network parallel to (100). A short Br⋯Br contact of 3.5114 (6) Å is also observed.

Related literature

For details and applications of pyrazole compounds, see: Isloor et al. (2009 ▶); Rai et al. (2008 ▶) Bradbury & Pucci (2008 ▶); Girisha et al. (2010 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H10BrN5OS

M = 340.21

Monoclinic,

a = 25.6080 (18) Å

b = 11.6686 (8) Å

c = 9.0823 (6) Å

β = 98.907 (2)°

V = 2681.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 3.22 mm−1

T = 296 K

0.48 × 0.33 × 0.17 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.306, T max = 0.609

15576 measured reflections

3869 independent reflections

2776 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.127

S = 1.03

3869 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.75 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 and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034726/lh5323sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034726/lh5323Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034726/lh5323Isup3.cml

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

C11H10BrN5OS	F(000) = 1360
Mr = 340.21	Dx = 1.686 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4204 reflections
a = 25.6080 (18) Å	θ = 2.9–27.8°
b = 11.6686 (8) Å	µ = 3.22 mm−1
c = 9.0823 (6) Å	T = 296 K
β = 98.907 (2)°	Slab, orange
V = 2681.2 (3) Å3	0.48 × 0.33 × 0.17 mm
Z = 8

Bruker APEXII DUO CCD area-detector diffractometer	3869 independent reflections
Radiation source: fine-focus sealed tube	2776 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 30.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −36→36
Tmin = 0.306, Tmax = 0.609	k = −16→14
15576 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0646P)2 + 2.3027P] where P = (Fo2 + 2Fc2)/3
3869 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.75 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.24780 (3)	0.67093 (6)	0.16175 (6)	0.04971 (18)
Br1	0.476115 (14)	1.36166 (3)	0.95277 (4)	0.07714 (17)
O1	0.29888 (8)	0.85438 (14)	0.39141 (19)	0.0476 (4)
N1	0.30362 (8)	0.65467 (16)	0.43648 (19)	0.0377 (4)
N2	0.32861 (9)	0.58425 (17)	0.5541 (2)	0.0442 (5)
N3	0.37576 (9)	0.85410 (17)	0.6771 (2)	0.0433 (4)
N4	0.36660 (9)	0.95754 (18)	0.6236 (2)	0.0432 (4)
N5	0.26122 (10)	0.4932 (2)	0.3443 (2)	0.0483 (5)
C1	0.35129 (9)	0.7684 (2)	0.6042 (2)	0.0399 (5)
C2	0.31496 (9)	0.77032 (19)	0.4632 (2)	0.0358 (4)
C3	0.35624 (11)	0.6506 (2)	0.6496 (3)	0.0464 (6)
C4	0.39352 (9)	1.0510 (2)	0.6975 (2)	0.0398 (5)
C5	0.43053 (11)	1.0338 (2)	0.8242 (3)	0.0536 (6)
H5A	0.4388	0.9600	0.8588	0.064*
C6	0.45488 (11)	1.1273 (3)	0.8982 (3)	0.0581 (7)
H6A	0.4794	1.1169	0.9840	0.070*
C7	0.44277 (10)	1.2359 (2)	0.8449 (3)	0.0500 (6)
C8	0.40611 (11)	1.2539 (2)	0.7174 (3)	0.0517 (6)
H8A	0.3983	1.3276	0.6818	0.062*
C9	0.38156 (11)	1.1601 (2)	0.6447 (3)	0.0498 (6)
H9A	0.3568	1.1705	0.5595	0.060*
C10	0.27077 (9)	0.6012 (2)	0.3187 (2)	0.0373 (5)
C11	0.38809 (16)	0.6072 (3)	0.7892 (4)	0.0753 (10)
H11A	0.3828	0.5261	0.7969	0.113*
H11B	0.3772	0.6450	0.8733	0.113*
H11C	0.4248	0.6224	0.7875	0.113*
H1N4	0.3475 (14)	0.980 (3)	0.548 (4)	0.064 (9)*
H1N5	0.2727 (15)	0.468 (3)	0.425 (4)	0.077 (11)*
H2N5	0.2458 (13)	0.456 (3)	0.275 (4)	0.057 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.0660 (4)	0.0450 (4)	0.0326 (3)	0.0018 (3)	−0.0098 (2)	0.0007 (2)
Br1	0.0707 (2)	0.0514 (2)	0.0982 (3)	−0.00776 (14)	−0.02193 (18)	−0.02813 (16)
O1	0.0595 (11)	0.0342 (9)	0.0437 (9)	0.0036 (7)	−0.0085 (8)	0.0020 (6)
N1	0.0453 (10)	0.0322 (10)	0.0316 (8)	−0.0025 (7)	−0.0064 (7)	0.0006 (6)
N2	0.0550 (12)	0.0331 (10)	0.0387 (9)	−0.0027 (9)	−0.0111 (8)	0.0047 (7)
N3	0.0467 (11)	0.0381 (11)	0.0420 (10)	−0.0061 (8)	−0.0032 (8)	−0.0022 (7)
N4	0.0470 (11)	0.0362 (11)	0.0422 (10)	−0.0034 (8)	−0.0064 (8)	−0.0040 (8)
N5	0.0642 (14)	0.0411 (12)	0.0341 (9)	−0.0113 (10)	−0.0092 (9)	−0.0014 (8)
C1	0.0442 (12)	0.0366 (12)	0.0350 (9)	−0.0020 (9)	−0.0055 (8)	−0.0002 (8)
C2	0.0408 (11)	0.0326 (11)	0.0327 (9)	0.0001 (9)	0.0018 (8)	−0.0002 (8)
C3	0.0529 (14)	0.0399 (13)	0.0406 (11)	−0.0057 (10)	−0.0112 (10)	0.0037 (9)
C4	0.0388 (11)	0.0379 (12)	0.0411 (10)	−0.0039 (9)	0.0012 (9)	−0.0064 (9)
C5	0.0528 (15)	0.0406 (14)	0.0599 (14)	0.0007 (11)	−0.0151 (11)	−0.0046 (11)
C6	0.0519 (15)	0.0527 (17)	0.0606 (15)	0.0019 (12)	−0.0203 (12)	−0.0123 (12)
C7	0.0441 (13)	0.0413 (14)	0.0609 (14)	−0.0045 (10)	−0.0036 (10)	−0.0158 (11)
C8	0.0554 (15)	0.0351 (13)	0.0600 (14)	−0.0030 (11)	−0.0053 (11)	−0.0044 (10)
C9	0.0531 (15)	0.0413 (14)	0.0492 (12)	−0.0033 (11)	−0.0104 (10)	−0.0018 (10)
C10	0.0412 (11)	0.0388 (12)	0.0301 (9)	−0.0009 (9)	−0.0006 (8)	−0.0038 (8)
C11	0.095 (2)	0.0536 (17)	0.0604 (17)	−0.0116 (17)	−0.0407 (16)	0.0130 (13)

S1—C10	1.667 (2)	C1—C2	1.462 (3)
Br1—C7	1.893 (2)	C3—C11	1.486 (3)
O1—C2	1.214 (3)	C4—C9	1.377 (4)
N1—C2	1.394 (3)	C4—C5	1.387 (3)
N1—C10	1.401 (3)	C5—C6	1.378 (4)
N1—N2	1.420 (3)	C5—H5A	0.9300
N2—C3	1.289 (3)	C6—C7	1.375 (4)
N3—C1	1.304 (3)	C6—H6A	0.9300
N3—N4	1.308 (3)	C7—C8	1.389 (4)
N4—C4	1.404 (3)	C8—C9	1.379 (4)
N4—H1N4	0.82 (3)	C8—H8A	0.9300
N5—C10	1.311 (3)	C9—H9A	0.9300
N5—H1N5	0.81 (4)	C11—H11A	0.9600
N5—H2N5	0.81 (4)	C11—H11B	0.9600
C1—C3	1.435 (3)	C11—H11C	0.9600
C2—N1—C10	130.42 (19)	C6—C5—H5A	120.3
C2—N1—N2	111.85 (17)	C4—C5—H5A	120.3
C10—N1—N2	117.67 (18)	C7—C6—C5	119.8 (2)
C3—N2—N1	107.16 (19)	C7—C6—H6A	120.1
C1—N3—N4	118.3 (2)	C5—C6—H6A	120.1
N3—N4—C4	119.5 (2)	C6—C7—C8	121.3 (2)
N3—N4—H1N4	131 (2)	C6—C7—Br1	118.24 (19)
C4—N4—H1N4	110 (2)	C8—C7—Br1	120.5 (2)
C10—N5—H1N5	117 (3)	C9—C8—C7	118.6 (3)
C10—N5—H2N5	117 (2)	C9—C8—H8A	120.7
H1N5—N5—H2N5	125 (4)	C7—C8—H8A	120.7
N3—C1—C3	125.1 (2)	C4—C9—C8	120.4 (2)
N3—C1—C2	128.6 (2)	C4—C9—H9A	119.8
C3—C1—C2	106.37 (19)	C8—C9—H9A	119.8
O1—C2—N1	130.2 (2)	N5—C10—N1	113.5 (2)
O1—C2—C1	126.8 (2)	N5—C10—S1	124.77 (17)
N1—C2—C1	103.00 (18)	N1—C10—S1	121.74 (17)
N2—C3—C1	111.6 (2)	C3—C11—H11A	109.5
N2—C3—C11	122.7 (2)	C3—C11—H11B	109.5
C1—C3—C11	125.7 (2)	H11A—C11—H11B	109.5
C9—C4—C5	120.5 (2)	C3—C11—H11C	109.5
C9—C4—N4	119.0 (2)	H11A—C11—H11C	109.5
C5—C4—N4	120.4 (2)	H11B—C11—H11C	109.5
C6—C5—C4	119.3 (3)
C2—N1—N2—C3	−2.1 (3)	C2—C1—C3—C11	−178.2 (3)
C10—N1—N2—C3	−179.5 (2)	N3—N4—C4—C9	−176.6 (2)
C1—N3—N4—C4	−178.2 (2)	N3—N4—C4—C5	1.5 (4)
N4—N3—C1—C3	−178.7 (2)	C9—C4—C5—C6	0.8 (4)
N4—N3—C1—C2	2.4 (4)	N4—C4—C5—C6	−177.4 (3)
C10—N1—C2—O1	0.6 (4)	C4—C5—C6—C7	−0.8 (5)
N2—N1—C2—O1	−176.3 (2)	C5—C6—C7—C8	0.3 (5)
C10—N1—C2—C1	179.5 (2)	C5—C6—C7—Br1	178.7 (2)
N2—N1—C2—C1	2.6 (2)	C6—C7—C8—C9	0.3 (4)
N3—C1—C2—O1	−4.0 (4)	Br1—C7—C8—C9	−178.1 (2)
C3—C1—C2—O1	176.9 (2)	C5—C4—C9—C8	−0.2 (4)
N3—C1—C2—N1	177.0 (3)	N4—C4—C9—C8	178.0 (2)
C3—C1—C2—N1	−2.0 (3)	C7—C8—C9—C4	−0.4 (4)
N1—N2—C3—C1	0.7 (3)	C2—N1—C10—N5	−167.1 (2)
N1—N2—C3—C11	179.8 (3)	N2—N1—C10—N5	9.7 (3)
N3—C1—C3—N2	−178.2 (3)	C2—N1—C10—S1	13.9 (4)
C2—C1—C3—N2	0.9 (3)	N2—N1—C10—S1	−169.28 (17)
N3—C1—C3—C11	2.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···O1	0.82 (4)	2.27 (4)	2.788 (3)	121 (3)
N5—H1N5···S1i	0.80 (4)	2.84 (4)	3.522 (2)	144 (3)
N5—H2N5···O1ii	0.82 (3)	2.11 (4)	2.925 (3)	175 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H1N4⋯O1	0.82 (4)	2.27 (4)	2.788 (3)	121 (3)
N5—H1N5⋯S1i	0.80 (4)	2.84 (4)	3.522 (2)	144 (3)
N5—H2N5⋯O1ii	0.82 (3)	2.11 (4)	2.925 (3)	175 (4)

Symmetry codes: (i) ; (ii) .