2-Chloro-N-[3-cyano-1-(3,4-dichloro-phen-yl)-1H-pyrazol-5-yl]acetamide.

In the title compound, C(12)H(7)Cl(3)N(4)O, the dihedral angle between the pyrazole and benzene rings is 35.6 (3)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds generating C(4) chains propagating in [100].

Related literature

For background to the properties of N-pyrazoles, see: Liu et al. (2010 ▶); Zhao et al. (2010 ▶).

Experimental

Crystal data

C12H7Cl3N4O

M = 329.57

Monoclinic,

a = 4.6280 (9) Å

b = 17.245 (3) Å

c = 17.468 (4) Å

β = 94.04 (3)°

V = 1390.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.66 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.827, T max = 0.937

5687 measured reflections

2564 independent reflections

1880 reflections with I > 2σ(I)

R int = 0.040

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.139

S = 1.01

2564 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008094/hb6649sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008094/hb6649Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008094/hb6649Isup3.cml

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

C12H7Cl3N4O	Dx = 1.574 Mg m−3
Mr = 329.57	Melting point: 473 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.6280 (9) Å	Cell parameters from 25 reflections
b = 17.245 (3) Å	θ = 9–13°
c = 17.468 (4) Å	µ = 0.66 mm−1
β = 94.04 (3)°	T = 293 K
V = 1390.7 (5) Å3	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm
F(000) = 664

Enraf–Nonius CAD-4 diffractometer	1880 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
Graphite monochromator	θmax = 25.4°, θmin = 1.7°
ω/2θ scans	h = 0→5
Absorption correction: ψ scan (North et al., 1968)	k = −20→20
Tmin = 0.827, Tmax = 0.937	l = −21→21
5687 measured reflections	3 standard reflections every 200 reflections
2564 independent reflections	intensity decay: 1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.139	w = 1/[σ2(Fo2) + (0.090P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2564 reflections	Δρmax = 0.31 e Å−3
182 parameters	Δρmin = −0.25 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (3)

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.

	x	y	z	Uiso*/Ueq
O	0.8240 (5)	0.38138 (13)	0.35313 (18)	0.0813 (8)
Cl1	−0.40136 (18)	0.21696 (4)	−0.00295 (5)	0.0641 (3)
C1	−0.0120 (6)	0.23735 (15)	0.11596 (15)	0.0438 (6)
H1A	−0.0419	0.1852	0.1266	0.053*
Cl2	−0.3173 (2)	0.39579 (5)	−0.03563 (5)	0.0738 (3)
N1	0.3510 (5)	0.24173 (12)	0.22197 (12)	0.0426 (5)
N2	0.4349 (5)	0.16733 (12)	0.21185 (13)	0.0488 (6)
C2	−0.1647 (6)	0.27227 (15)	0.05502 (15)	0.0447 (6)
Cl3	0.69321 (17)	0.53185 (4)	0.41501 (5)	0.0602 (3)
C3	−0.1258 (7)	0.35054 (16)	0.04024 (15)	0.0496 (7)
N3	0.8375 (9)	0.01856 (18)	0.2981 (2)	0.0950 (11)
N4	0.3729 (4)	0.34308 (13)	0.31669 (13)	0.0456 (6)
H4A	0.1933	0.3562	0.3119	0.055*
C4	0.0724 (8)	0.39217 (16)	0.08606 (17)	0.0582 (8)
H4B	0.0990	0.4446	0.0762	0.070*
C5	0.2322 (7)	0.35752 (15)	0.14625 (16)	0.0521 (7)
H5A	0.3688	0.3857	0.1763	0.062*
C6	0.1850 (6)	0.27986 (14)	0.16112 (14)	0.0412 (6)
C7	0.4522 (5)	0.26933 (16)	0.29174 (15)	0.0425 (6)
C8	0.6121 (7)	0.21299 (17)	0.32747 (17)	0.0541 (7)
H8A	0.7116	0.2150	0.3756	0.065*
C9	0.5948 (7)	0.15113 (15)	0.27610 (16)	0.0489 (7)
C10	0.7278 (8)	0.07622 (19)	0.28682 (18)	0.0644 (9)
C11	0.5659 (6)	0.39367 (15)	0.34757 (15)	0.0426 (6)
C12	0.4304 (6)	0.46675 (15)	0.37652 (18)	0.0503 (7)
H12A	0.3004	0.4534	0.4157	0.060*
H12B	0.3171	0.4916	0.3346	0.060*

	U11	U22	U33	U12	U13	U23
O	0.0337 (12)	0.0558 (13)	0.154 (3)	0.0049 (10)	0.0002 (13)	−0.0304 (15)
Cl1	0.0735 (6)	0.0549 (5)	0.0603 (5)	−0.0049 (4)	−0.0212 (4)	0.0010 (3)
C1	0.0494 (16)	0.0346 (13)	0.0471 (15)	−0.0013 (12)	0.0018 (12)	0.0003 (11)
Cl2	0.0949 (7)	0.0570 (5)	0.0673 (5)	0.0099 (4)	−0.0091 (5)	0.0194 (4)
N1	0.0480 (13)	0.0351 (11)	0.0440 (12)	−0.0008 (10)	−0.0004 (10)	−0.0051 (9)
N2	0.0626 (15)	0.0326 (11)	0.0507 (13)	0.0051 (10)	0.0013 (11)	−0.0040 (10)
C2	0.0482 (15)	0.0410 (14)	0.0448 (14)	0.0018 (12)	0.0021 (12)	−0.0013 (11)
Cl3	0.0585 (5)	0.0442 (4)	0.0767 (5)	−0.0064 (3)	−0.0043 (4)	−0.0129 (3)
C3	0.0626 (19)	0.0423 (15)	0.0440 (15)	0.0078 (13)	0.0044 (13)	0.0068 (11)
N3	0.138 (3)	0.0591 (19)	0.087 (2)	0.036 (2)	−0.001 (2)	0.0074 (16)
N4	0.0297 (11)	0.0483 (13)	0.0576 (13)	0.0067 (9)	−0.0046 (10)	−0.0182 (11)
C4	0.080 (2)	0.0360 (14)	0.0583 (18)	−0.0048 (14)	0.0049 (17)	0.0047 (12)
C5	0.067 (2)	0.0373 (14)	0.0515 (16)	−0.0100 (13)	0.0020 (14)	−0.0023 (12)
C6	0.0457 (14)	0.0339 (13)	0.0441 (14)	−0.0012 (11)	0.0040 (12)	−0.0037 (10)
C7	0.0361 (14)	0.0427 (14)	0.0485 (15)	0.0016 (11)	0.0005 (12)	−0.0111 (12)
C8	0.0557 (18)	0.0526 (17)	0.0526 (16)	0.0086 (14)	−0.0061 (14)	−0.0082 (13)
C9	0.0557 (17)	0.0393 (14)	0.0508 (16)	0.0054 (13)	−0.0012 (13)	−0.0021 (12)
C10	0.086 (2)	0.0515 (18)	0.0538 (17)	0.0120 (17)	−0.0060 (17)	−0.0009 (14)
C11	0.0333 (14)	0.0406 (14)	0.0535 (16)	0.0032 (11)	−0.0002 (12)	−0.0024 (11)
C12	0.0385 (15)	0.0445 (15)	0.0673 (18)	0.0007 (12)	−0.0006 (13)	−0.0132 (13)

O—C11	1.210 (3)	N4—C11	1.335 (3)
Cl1—C2	1.726 (3)	N4—C7	1.402 (3)
C1—C2	1.374 (4)	N4—H4A	0.8600
C1—C6	1.375 (3)	C4—C5	1.378 (4)
C1—H1A	0.9300	C4—H4B	0.9300
Cl2—C3	1.728 (3)	C5—C6	1.384 (4)
N1—N2	1.356 (3)	C5—H5A	0.9300
N1—C7	1.360 (3)	C7—C8	1.348 (4)
N1—C6	1.427 (3)	C8—C9	1.393 (4)
N2—C9	1.330 (3)	C8—H8A	0.9300
C2—C3	1.388 (4)	C9—C10	1.438 (4)
Cl3—C12	1.754 (3)	C11—C12	1.511 (4)
C3—C4	1.376 (4)	C12—H12A	0.9700
N3—C10	1.127 (4)	C12—H12B	0.9700
C2—C1—C6	119.7 (2)	C1—C6—C5	121.0 (3)
C2—C1—H1A	120.2	C1—C6—N1	118.8 (2)
C6—C1—H1A	120.2	C5—C6—N1	120.1 (2)
N2—N1—C7	111.4 (2)	C8—C7—N1	107.8 (2)
N2—N1—C6	118.88 (19)	C8—C7—N4	131.1 (2)
C7—N1—C6	129.7 (2)	N1—C7—N4	121.0 (2)
C9—N2—N1	103.7 (2)	C7—C8—C9	104.4 (3)
C1—C2—C3	120.3 (3)	C7—C8—H8A	127.8
C1—C2—Cl1	118.9 (2)	C9—C8—H8A	127.8
C3—C2—Cl1	120.9 (2)	N2—C9—C8	112.7 (2)
C4—C3—C2	119.3 (3)	N2—C9—C10	120.4 (2)
C4—C3—Cl2	119.7 (2)	C8—C9—C10	126.8 (3)
C2—C3—Cl2	121.0 (2)	N3—C10—C9	177.1 (4)
C11—N4—C7	122.4 (2)	O—C11—N4	123.1 (2)
C11—N4—H4A	118.8	O—C11—C12	123.3 (2)
C7—N4—H4A	118.8	N4—C11—C12	113.5 (2)
C3—C4—C5	121.2 (3)	C11—C12—Cl3	111.68 (19)
C3—C4—H4B	119.4	C11—C12—H12A	109.3
C5—C4—H4B	119.4	Cl3—C12—H12A	109.3
C4—C5—C6	118.6 (3)	C11—C12—H12B	109.3
C4—C5—H5A	120.7	Cl3—C12—H12B	109.3
C6—C5—H5A	120.7	H12A—C12—H12B	107.9
C7—N1—N2—C9	−1.5 (3)	N2—N1—C7—C8	1.7 (3)
C6—N1—N2—C9	176.8 (2)	C6—N1—C7—C8	−176.4 (3)
C6—C1—C2—C3	−1.6 (4)	N2—N1—C7—N4	−175.1 (2)
C6—C1—C2—Cl1	177.7 (2)	C6—N1—C7—N4	6.9 (4)
C1—C2—C3—C4	1.6 (4)	C11—N4—C7—C8	51.2 (5)
Cl1—C2—C3—C4	−177.7 (2)	C11—N4—C7—N1	−132.9 (3)
C1—C2—C3—Cl2	−179.5 (2)	N1—C7—C8—C9	−1.1 (3)
Cl1—C2—C3—Cl2	1.1 (4)	N4—C7—C8—C9	175.2 (3)
C2—C3—C4—C5	−0.1 (5)	N1—N2—C9—C8	0.8 (3)
Cl2—C3—C4—C5	−178.9 (2)	N1—N2—C9—C10	−179.3 (3)
C3—C4—C5—C6	−1.5 (5)	C7—C8—C9—N2	0.2 (4)
C2—C1—C6—C5	0.1 (4)	C7—C8—C9—C10	−179.7 (3)
C2—C1—C6—N1	−177.2 (2)	N2—C9—C10—N3	176 (8)
C4—C5—C6—C1	1.5 (4)	C8—C9—C10—N3	−4 (9)
C4—C5—C6—N1	178.7 (3)	C7—N4—C11—O	3.5 (5)
N2—N1—C6—C1	35.1 (3)	C7—N4—C11—C12	−175.1 (2)
C7—N1—C6—C1	−147.0 (3)	O—C11—C12—Cl3	2.4 (4)
N2—N1—C6—C5	−142.2 (3)	N4—C11—C12—Cl3	−179.0 (2)
C7—N1—C6—C5	35.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···Oi	0.86	1.95	2.743 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯Oi	0.86	1.95	2.743 (3)	153

Symmetry code: (i) .