(E)-4-Chloro-N-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methyl-ene]aniline.

In the title compound, C(17)H(13)Cl(2)N(3), the dihedral angle between the pyrazole ring system and 4-chloro-phenyl ring is 26.1 (2)°. The C=N bond linking the two aromatic rings has an E conformation.

Related literature

For the biological properties of pyrazoles, see: Pimerova & Voronina (2001 ▶); Selvam et al. (2005 ▶). For the biological activity of Schiff bases, see: Rajavel et al. (2008 ▶); Yu et al. (2007 ▶). For a related stucture, see: Sun et al. (2007 ▶).

Experimental

Crystal data

C17H13Cl2N3

M = 330.20

Orthorhombic,

a = 13.6471 (6) Å

b = 15.6315 (3) Å

c = 7.3514 (6) Å

V = 1568.24 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 296 K

0.39 × 0.34 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (; Higashi, 1995 ▶) T min = 0.839, T max = 0.960

14704 measured reflections

3558 independent reflections

2533 reflections with F 2 > 2σ(F 2)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.099

S = 1.00

3558 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1627 Friedel pairs

Flack parameter: −0.02 (6)

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2007 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035727/rk2165sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035727/rk2165Isup2.hkl

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

C17H13Cl2N3	Dx = 1.399 Mg m−3
Mr = 330.20	Melting point: 434 K
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2c -2ac	Cell parameters from 10504 reflections
a = 13.6471 (6) Å	θ = 3.0–27.4°
b = 15.6315 (3) Å	µ = 0.41 mm−1
c = 7.3514 (6) Å	T = 296 K
V = 1568.24 (15) Å3	Plate, colourless
Z = 4	0.39 × 0.34 × 0.10 mm
F(000) = 680.00

Rigaku R-AXIS RAPID diffractometer	2533 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1	Rint = 0.038
ω scans	θmax = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→17
Tmin = 0.839, Tmax = 0.960	k = −20→20
14704 measured reflections	l = −9→9
3558 independent reflections

Refinement on F2	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032	w = 1/[σ2(Fo2) + (0.055P)2 + 0.089P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.21 e Å−3
3558 reflections	Δρmin = −0.24 e Å−3
201 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: Direct	Extinction coefficient: 0.0049 (8)
Secondary atom site location: Difmap	Absolute structure: Flack (1983), 1627 Friedel pairs
Hydrogen site location: Geom	Flack parameter: −0.02 (6)

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 > 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
Cl1	0.42986 (4)	0.48323 (3)	0.33646 (10)	0.04844 (15)
Cl2	0.32167 (6)	−0.08853 (5)	0.43233 (18)	0.0893 (3)
N1	0.71398 (12)	0.47004 (11)	0.3343 (3)	0.0478 (4)
N2	0.62562 (11)	0.51191 (10)	0.3340 (2)	0.0391 (3)
N3	0.56891 (12)	0.22175 (11)	0.3631 (3)	0.0480 (5)
C1	0.55095 (13)	0.45498 (12)	0.3464 (3)	0.0395 (4)
C2	0.58944 (14)	0.37384 (12)	0.3577 (3)	0.0411 (4)
C3	0.69251 (14)	0.38699 (14)	0.3490 (4)	0.0452 (5)
C4	0.77319 (18)	0.32253 (16)	0.3538 (5)	0.0629 (7)
C5	0.53181 (17)	0.29634 (13)	0.3730 (3)	0.0446 (5)
C6	0.50557 (16)	0.14994 (13)	0.3773 (3)	0.0436 (5)
C7	0.5429 (2)	0.07657 (16)	0.4568 (4)	0.0565 (6)
C8	0.4858 (2)	0.00375 (17)	0.4763 (4)	0.0624 (7)
C9	0.3916 (2)	0.00400 (16)	0.4118 (3)	0.0539 (6)
C10	0.35333 (17)	0.07546 (14)	0.3280 (5)	0.0548 (6)
C11	0.41003 (16)	0.14831 (14)	0.3120 (3)	0.0490 (6)
C12	0.62388 (16)	0.60273 (12)	0.3108 (3)	0.0393 (5)
C13	0.55665 (18)	0.65294 (14)	0.4025 (3)	0.0467 (5)
C14	0.55583 (19)	0.74051 (14)	0.3718 (3)	0.0539 (6)
C15	0.6222 (2)	0.77754 (17)	0.2553 (3)	0.0558 (7)
C16	0.6905 (2)	0.72688 (18)	0.1672 (3)	0.0550 (6)
C17	0.69122 (17)	0.63883 (17)	0.1930 (3)	0.0467 (5)
H5	0.4646	0.3013	0.3909	0.054*
H7	0.6073	0.0761	0.4978	0.068*
H8	0.5111	−0.0447	0.5326	0.075*
H10	0.2898	0.0746	0.2825	0.066*
H11	0.3840	0.1968	0.2569	0.059*
H13	0.5126	0.6284	0.4837	0.056*
H14	0.5098	0.7746	0.4307	0.065*
H15	0.6213	0.8363	0.2357	0.067*
H16	0.7363	0.7520	0.0901	0.066*
H17	0.7363	0.6047	0.1319	0.056*
H41	0.7578	0.2762	0.2731	0.076*
H42	0.7803	0.3010	0.4754	0.076*
H43	0.8333	0.3490	0.3160	0.076*

	U11	U22	U33	U12	U13	U23
Cl1	0.0317 (2)	0.0431 (2)	0.0705 (3)	−0.0001 (2)	0.0023 (3)	0.0004 (3)
Cl2	0.0752 (5)	0.0612 (4)	0.1317 (7)	−0.0261 (3)	0.0065 (5)	0.0141 (5)
N1	0.0334 (8)	0.0459 (10)	0.0642 (12)	−0.0012 (7)	−0.0001 (12)	0.0000 (13)
N2	0.0288 (8)	0.0372 (8)	0.0513 (9)	−0.0004 (6)	0.0006 (11)	0.0029 (10)
N3	0.0417 (9)	0.0363 (9)	0.0659 (14)	−0.0003 (7)	−0.0003 (10)	0.0005 (10)
C1	0.0321 (9)	0.0388 (9)	0.0476 (11)	−0.0005 (8)	0.0036 (12)	−0.0007 (12)
C2	0.0373 (10)	0.0387 (10)	0.0473 (12)	−0.0003 (8)	0.0025 (11)	0.0031 (11)
C3	0.0367 (10)	0.0467 (11)	0.0522 (12)	0.0019 (8)	−0.0021 (12)	0.0010 (12)
C4	0.0469 (13)	0.0501 (13)	0.092 (2)	0.0085 (11)	−0.0008 (16)	0.0068 (17)
C5	0.0400 (11)	0.0424 (10)	0.0515 (15)	−0.0033 (9)	0.0034 (10)	0.0036 (11)
C6	0.0409 (11)	0.0384 (10)	0.0515 (14)	0.0015 (8)	0.0012 (10)	0.0010 (10)
C7	0.0449 (13)	0.0452 (13)	0.0795 (18)	−0.0018 (10)	−0.0114 (14)	0.0083 (13)
C8	0.0650 (19)	0.0426 (13)	0.0795 (18)	−0.0026 (11)	−0.0083 (15)	0.0170 (13)
C9	0.0514 (14)	0.0456 (12)	0.0647 (15)	−0.0067 (11)	0.0055 (13)	0.0008 (12)
C10	0.0360 (10)	0.0501 (12)	0.0782 (16)	0.0023 (10)	−0.0013 (15)	−0.0023 (14)
C11	0.0445 (13)	0.0371 (11)	0.0656 (16)	0.0045 (8)	−0.0004 (13)	0.0010 (12)
C12	0.0353 (11)	0.0362 (10)	0.0463 (13)	−0.0054 (8)	−0.0049 (10)	−0.0002 (10)
C13	0.0462 (13)	0.0439 (11)	0.0501 (13)	−0.0043 (10)	0.0019 (11)	−0.0011 (10)
C14	0.0535 (14)	0.0424 (11)	0.0658 (18)	0.0032 (10)	−0.0061 (13)	−0.0073 (13)
C15	0.0620 (18)	0.0413 (13)	0.0642 (15)	−0.0111 (12)	−0.0165 (14)	0.0050 (12)
C16	0.0493 (14)	0.0580 (16)	0.0578 (14)	−0.0171 (12)	−0.0065 (12)	0.0147 (13)
C17	0.0377 (12)	0.0513 (13)	0.0510 (13)	−0.0063 (10)	−0.0009 (10)	0.0039 (11)

Cl1—C1	1.7121 (19)	C12—C17	1.383 (3)
Cl2—C9	1.740 (2)	C13—C14	1.387 (3)
N1—N2	1.372 (2)	C14—C15	1.375 (3)
N1—C3	1.335 (2)	C15—C16	1.384 (3)
N2—C1	1.356 (2)	C16—C17	1.389 (3)
N2—C12	1.430 (2)	C4—H41	0.960
N3—C5	1.273 (2)	C4—H42	0.960
N3—C6	1.421 (2)	C4—H43	0.960
C1—C2	1.375 (2)	C5—H5	0.930
C2—C3	1.423 (2)	C7—H7	0.930
C2—C5	1.449 (3)	C8—H8	0.930
C3—C4	1.493 (3)	C10—H10	0.930
C6—C7	1.384 (3)	C11—H11	0.930
C6—C11	1.390 (3)	C13—H13	0.930
C7—C8	1.387 (3)	C14—H14	0.930
C8—C9	1.370 (4)	C15—H15	0.930
C9—C10	1.379 (3)	C16—H16	0.930
C10—C11	1.382 (3)	C17—H17	0.930
C12—C13	1.383 (3)
N2—N1—C3	105.73 (16)	C14—C15—C16	119.6 (2)
N1—N2—C1	110.32 (15)	C15—C16—C17	120.5 (2)
N1—N2—C12	119.23 (15)	C12—C17—C16	119.0 (2)
C1—N2—C12	130.32 (16)	C3—C4—H41	109.5
C5—N3—C6	118.52 (18)	C3—C4—H42	109.5
Cl1—C1—N2	123.59 (15)	C3—C4—H43	109.5
Cl1—C1—C2	127.52 (15)	H41—C4—H42	109.5
N2—C1—C2	108.80 (16)	H41—C4—H43	109.5
C1—C2—C3	103.98 (18)	H42—C4—H43	109.5
C1—C2—C5	124.65 (19)	N3—C5—H5	118.5
C3—C2—C5	131.37 (19)	C2—C5—H5	118.5
N1—C3—C2	111.16 (18)	C6—C7—H7	119.4
N1—C3—C4	119.75 (19)	C8—C7—H7	119.4
C2—C3—C4	129.1 (2)	C7—C8—H8	120.4
N3—C5—C2	123.1 (2)	C9—C8—H8	120.4
N3—C6—C7	117.5 (2)	C9—C10—H10	120.2
N3—C6—C11	124.1 (2)	C11—C10—H10	120.2
C7—C6—C11	118.4 (2)	C6—C11—H11	119.6
C6—C7—C8	121.1 (2)	C10—C11—H11	119.6
C7—C8—C9	119.3 (2)	C12—C13—H13	120.5
Cl2—C9—C8	118.8 (2)	C14—C13—H13	120.5
Cl2—C9—C10	120.3 (2)	C13—C14—H14	119.6
C8—C9—C10	120.8 (2)	C15—C14—H14	119.6
C9—C10—C11	119.6 (2)	C14—C15—H15	120.2
C6—C11—C10	120.7 (2)	C16—C15—H15	120.2
N2—C12—C13	121.07 (19)	C15—C16—H16	119.7
N2—C12—C17	117.95 (19)	C17—C16—H16	119.7
C13—C12—C17	121.0 (2)	C12—C17—H17	120.5
C12—C13—C14	119.1 (2)	C16—C17—H17	120.5
C13—C14—C15	120.8 (2)
N2—N1—C3—C2	0.2 (3)	C3—C2—C5—N3	−7.3 (4)
N2—N1—C3—C4	−179.9 (2)	C5—C2—C3—N1	179.7 (2)
C3—N1—N2—C1	−0.7 (3)	C5—C2—C3—C4	−0.2 (4)
C3—N1—N2—C12	−177.0 (2)	N3—C6—C7—C8	179.8 (2)
N1—N2—C1—Cl1	−176.0 (2)	N3—C6—C11—C10	178.9 (2)
N1—N2—C1—C2	0.8 (3)	C7—C6—C11—C10	0.7 (4)
N1—N2—C12—C13	−143.5 (2)	C11—C6—C7—C8	−1.9 (4)
N1—N2—C12—C17	36.8 (3)	C6—C7—C8—C9	1.6 (4)
C1—N2—C12—C13	41.0 (3)	C7—C8—C9—Cl2	178.5 (2)
C1—N2—C12—C17	−138.7 (2)	C7—C8—C9—C10	0.1 (3)
C12—N2—C1—Cl1	−0.2 (3)	Cl2—C9—C10—C11	−179.7 (2)
C12—N2—C1—C2	176.6 (2)	C8—C9—C10—C11	−1.3 (4)
C5—N3—C6—C7	−147.9 (2)	C9—C10—C11—C6	0.9 (4)
C5—N3—C6—C11	33.9 (3)	N2—C12—C13—C14	−178.2 (2)
C6—N3—C5—C2	−179.1 (2)	N2—C12—C17—C16	179.6 (2)
Cl1—C1—C2—C3	176.1 (2)	C13—C12—C17—C16	−0.1 (3)
Cl1—C1—C2—C5	−3.4 (4)	C17—C12—C13—C14	1.5 (3)
N2—C1—C2—C3	−0.6 (3)	C12—C13—C14—C15	−1.6 (3)
N2—C1—C2—C5	179.87 (19)	C13—C14—C15—C16	0.2 (4)
C1—C2—C3—N1	0.2 (3)	C14—C15—C16—C17	1.2 (4)
C1—C2—C3—C4	−179.6 (3)	C15—C16—C17—C12	−1.3 (3)
C1—C2—C5—N3	172.0 (2)