5-Chloro-4-[(2-chloro­benzoyl­hydrazono)methyl]-3-methyl-1-phenyl-1H-pyrazole

Wen, L.-R.; Qi, W.-Y.; Zuo, Z.-Q.; Li, M.

doi:10.1107/S1600536806019131

5-Chloro-4-[(2-chlorobenzoylhydrazono)methyl]-3-methyl-1-phenyl-1H-pyrazole

L.-R. Wen, W.-Y. Qi, Z.-Q. Zuo and M. Li

In the title compound, C₁₈H₁₄C₁₂N₄O, centrosymmetrically related molecules are linked into dimers by intermolecular N—H

O hydrogen bonds. In the crystal structure, the molecules interact through intermolecular C—H

Cl hydrogen bonds, forming a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019131/rz2029sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019131/rz2029Isup2.hkl Contains datablock I

CCDC reference: 610877

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.035
wR factor = 0.102
Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

5-Chloro-4-(2-chlorobenzoylhydrazino)methylidene-3-methyl-1-phenyl-1H-pyrazole top

Crystal data top

C₁₈H₁₄Cl₂N₄O	Z = 8
M_r = 373.23	F(000) = 1536
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3108 reflections
a = 28.01 (2) Å	θ = 2.9–24.3°
b = 6.199 (5) Å	µ = 0.38 mm⁻¹
c = 23.535 (18) Å	T = 293 K
β = 119.199 (9)°	Block, colourless
V = 3567 (5) Å³	0.32 × 0.28 × 0.26 mm

Data collection top

Bruker APEX-II CCD area-detector diffractometer	3145 independent reflections
Radiation source: fine-focus sealed tube	2485 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
φ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −32→33
T_min = 0.884, T_max = 0.907	k = −6→7
9192 measured reflections	l = −25→28

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0571P)² + 0.8269P] where P = (F_o² + 2F_c²)/3
3145 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.13913 (3)	1.11082 (11)	0.64746 (4)	0.0980 (3)
Cl2	0.001588 (17)	0.66442 (8)	0.34635 (3)	0.06046 (18)
O1	0.05878 (5)	1.6294 (2)	0.56587 (7)	0.0615 (4)
N1	0.05848 (6)	1.3433 (3)	0.50707 (8)	0.0540 (4)
H1	0.0234	1.3335	0.4876	0.065*
N2	0.08847 (5)	1.2082 (2)	0.49021 (7)	0.0507 (4)
N3	0.10581 (5)	0.6708 (2)	0.36951 (7)	0.0458 (4)
N4	0.15388 (6)	0.7819 (3)	0.40307 (8)	0.0539 (4)
C1	0.17409 (8)	1.3165 (3)	0.63421 (10)	0.0538 (5)
C2	0.23062 (9)	1.3133 (4)	0.66723 (11)	0.0733 (6)
H2	0.2493	1.2024	0.6963	0.088*
C3	0.25865 (9)	1.4742 (4)	0.65686 (13)	0.0851 (8)
H3	0.2967	1.4707	0.6780	0.102*
C4	0.23131 (8)	1.6400 (4)	0.61571 (14)	0.0853 (8)
H4	0.2507	1.7500	0.6092	0.102*
C5	0.17508 (8)	1.6448 (3)	0.58388 (11)	0.0641 (6)
H5	0.1568	1.7605	0.5568	0.077*
C6	0.14540 (6)	1.4807 (3)	0.59146 (8)	0.0426 (4)
C7	0.08428 (7)	1.4909 (3)	0.55424 (9)	0.0467 (4)
C8	0.06231 (7)	1.0602 (3)	0.44959 (9)	0.0473 (4)
H8	0.0252	1.0413	0.4350	0.057*
C9	0.09028 (7)	0.9207 (3)	0.42586 (8)	0.0438 (4)
C10	0.14482 (7)	0.9313 (3)	0.43674 (9)	0.0507 (5)
C11	0.18958 (8)	1.0849 (4)	0.47850 (12)	0.0726 (6)
H11A	0.2225	1.0462	0.4778	0.109*
H11B	0.1959	1.0781	0.5224	0.109*
H11C	0.1791	1.2290	0.4621	0.109*
C12	0.06741 (6)	0.7539 (3)	0.38270 (8)	0.0427 (4)
C13	0.10118 (7)	0.5118 (3)	0.32348 (8)	0.0427 (4)
C14	0.12442 (7)	0.5520 (3)	0.28442 (9)	0.0526 (5)
H14	0.1434	0.6795	0.2889	0.063*
C15	0.11902 (8)	0.4002 (4)	0.23876 (10)	0.0646 (6)
H15	0.1344	0.4260	0.2122	0.077*
C16	0.09126 (9)	0.2117 (4)	0.23228 (11)	0.0702 (6)
H16	0.0874	0.1112	0.2010	0.084*
C17	0.06932 (10)	0.1713 (3)	0.27156 (12)	0.0694 (6)
H17	0.0510	0.0422	0.2675	0.083*
C18	0.07412 (8)	0.3209 (3)	0.31741 (10)	0.0567 (5)
H18	0.0591	0.2926	0.3442	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0986 (5)	0.0762 (4)	0.1374 (7)	−0.0006 (3)	0.0717 (5)	0.0358 (4)
Cl2	0.0377 (3)	0.0675 (3)	0.0724 (4)	−0.0124 (2)	0.0240 (2)	−0.0226 (2)
O1	0.0391 (7)	0.0716 (9)	0.0729 (9)	−0.0030 (6)	0.0267 (7)	−0.0276 (7)
N1	0.0320 (7)	0.0673 (10)	0.0604 (10)	−0.0058 (7)	0.0208 (7)	−0.0241 (8)
N2	0.0385 (8)	0.0620 (10)	0.0537 (9)	−0.0033 (7)	0.0240 (7)	−0.0163 (8)
N3	0.0399 (8)	0.0503 (9)	0.0487 (9)	−0.0034 (6)	0.0229 (7)	−0.0065 (7)
N4	0.0369 (8)	0.0657 (10)	0.0607 (10)	−0.0087 (7)	0.0252 (7)	−0.0131 (8)
C1	0.0532 (11)	0.0552 (11)	0.0569 (12)	−0.0015 (9)	0.0299 (10)	0.0004 (9)
C2	0.0548 (12)	0.0811 (15)	0.0663 (14)	0.0151 (11)	0.0156 (11)	0.0152 (12)
C3	0.0369 (11)	0.0941 (18)	0.0999 (19)	−0.0046 (12)	0.0144 (12)	0.0083 (15)
C4	0.0424 (12)	0.0885 (17)	0.113 (2)	−0.0125 (11)	0.0283 (13)	0.0182 (15)
C5	0.0426 (10)	0.0679 (13)	0.0708 (14)	−0.0047 (9)	0.0192 (10)	0.0139 (11)
C6	0.0360 (8)	0.0523 (10)	0.0415 (10)	−0.0040 (7)	0.0204 (8)	−0.0068 (8)
C7	0.0364 (9)	0.0567 (11)	0.0503 (11)	−0.0061 (8)	0.0237 (8)	−0.0091 (9)
C8	0.0353 (9)	0.0569 (11)	0.0492 (10)	−0.0072 (8)	0.0202 (8)	−0.0110 (9)
C9	0.0378 (9)	0.0505 (10)	0.0428 (10)	−0.0049 (7)	0.0193 (8)	−0.0063 (8)
C10	0.0392 (9)	0.0595 (11)	0.0523 (11)	−0.0088 (8)	0.0215 (8)	−0.0106 (9)
C11	0.0454 (11)	0.0862 (15)	0.0863 (16)	−0.0222 (11)	0.0322 (11)	−0.0329 (13)
C12	0.0340 (8)	0.0495 (10)	0.0456 (10)	−0.0032 (7)	0.0203 (8)	−0.0033 (8)
C13	0.0399 (9)	0.0462 (10)	0.0405 (9)	0.0079 (7)	0.0185 (8)	0.0015 (8)
C14	0.0469 (10)	0.0615 (12)	0.0550 (11)	0.0077 (8)	0.0291 (9)	0.0056 (9)
C15	0.0612 (12)	0.0892 (16)	0.0531 (12)	0.0215 (12)	0.0355 (10)	0.0059 (11)
C16	0.0686 (14)	0.0721 (15)	0.0677 (14)	0.0162 (11)	0.0315 (12)	−0.0168 (11)
C17	0.0792 (15)	0.0483 (12)	0.0862 (16)	0.0031 (10)	0.0447 (13)	−0.0126 (11)
C18	0.0719 (13)	0.0473 (11)	0.0619 (12)	0.0038 (9)	0.0414 (11)	0.0033 (9)

Geometric parameters (Å, º) top

Cl1—C1	1.726 (2)	C6—C7	1.496 (3)
Cl2—C12	1.703 (2)	C8—C9	1.450 (2)
O1—C7	1.230 (2)	C8—H8	0.9300
N1—C7	1.345 (2)	C9—C12	1.370 (3)
N1—N2	1.375 (2)	C9—C10	1.422 (3)
N1—H1	0.8600	C10—C11	1.497 (3)
N2—C8	1.268 (2)	C11—H11A	0.9600
N3—C12	1.358 (2)	C11—H11B	0.9600
N3—N4	1.369 (2)	C11—H11C	0.9600
N3—C13	1.423 (2)	C13—C18	1.375 (3)
N4—C10	1.321 (2)	C13—C14	1.384 (2)
C1—C6	1.380 (3)	C14—C15	1.380 (3)
C1—C2	1.382 (3)	C14—H14	0.9300
C2—C3	1.363 (3)	C15—C16	1.370 (3)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.363 (3)	C16—C17	1.360 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.375 (3)	C17—C18	1.379 (3)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.379 (3)	C18—H18	0.9300
C5—H5	0.9300

C7—N1—N2	119.64 (14)	C12—C9—C8	126.22 (15)
C7—N1—H1	120.2	C10—C9—C8	129.64 (16)
N2—N1—H1	120.2	N4—C10—C9	111.29 (15)
C8—N2—N1	116.63 (15)	N4—C10—C11	119.67 (17)
C12—N3—N4	110.04 (15)	C9—C10—C11	129.03 (17)
C12—N3—C13	130.44 (14)	C10—C11—H11A	109.5
N4—N3—C13	119.12 (13)	C10—C11—H11B	109.5
C10—N4—N3	106.04 (14)	H11A—C11—H11B	109.5
C6—C1—C2	121.35 (18)	C10—C11—H11C	109.5
C6—C1—Cl1	119.76 (15)	H11A—C11—H11C	109.5
C2—C1—Cl1	118.89 (17)	H11B—C11—H11C	109.5
C3—C2—C1	119.4 (2)	N3—C12—C9	108.65 (14)
C3—C2—H2	120.3	N3—C12—Cl2	123.07 (14)
C1—C2—H2	120.3	C9—C12—Cl2	128.21 (13)
C2—C3—C4	120.4 (2)	C18—C13—C14	120.00 (17)
C2—C3—H3	119.8	C18—C13—N3	121.07 (16)
C4—C3—H3	119.8	C14—C13—N3	118.93 (17)
C3—C4—C5	120.0 (2)	C15—C14—C13	119.09 (19)
C3—C4—H4	120.0	C15—C14—H14	120.5
C5—C4—H4	120.0	C13—C14—H14	120.5
C4—C5—C6	121.1 (2)	C16—C15—C14	120.59 (19)
C4—C5—H5	119.5	C16—C15—H15	119.7
C6—C5—H5	119.5	C14—C15—H15	119.7
C5—C6—C1	117.69 (17)	C17—C16—C15	120.1 (2)
C5—C6—C7	118.86 (17)	C17—C16—H16	120.0
C1—C6—C7	123.44 (16)	C15—C16—H16	120.0
O1—C7—N1	121.45 (16)	C16—C17—C18	120.3 (2)
O1—C7—C6	121.48 (16)	C16—C17—H17	119.9
N1—C7—C6	117.07 (15)	C18—C17—H17	119.9
N2—C8—C9	119.98 (16)	C13—C18—C17	119.92 (19)
N2—C8—H8	120.0	C13—C18—H18	120.0
C9—C8—H8	120.0	C17—C18—H18	120.0
C12—C9—C10	103.98 (15)

C7—N1—N2—C8	173.96 (17)	C12—C9—C10—N4	−0.4 (2)
C12—N3—N4—C10	0.3 (2)	C8—C9—C10—N4	−175.92 (18)
C13—N3—N4—C10	173.78 (15)	C12—C9—C10—C11	178.7 (2)
C6—C1—C2—C3	−0.8 (3)	C8—C9—C10—C11	3.1 (4)
Cl1—C1—C2—C3	179.6 (2)	N4—N3—C12—C9	−0.5 (2)
C1—C2—C3—C4	1.8 (4)	C13—N3—C12—C9	−173.06 (16)
C2—C3—C4—C5	−0.6 (4)	N4—N3—C12—Cl2	176.61 (13)
C3—C4—C5—C6	−1.7 (4)	C13—N3—C12—Cl2	4.1 (3)
C4—C5—C6—C1	2.7 (3)	C10—C9—C12—N3	0.5 (2)
C4—C5—C6—C7	−178.3 (2)	C8—C9—C12—N3	176.28 (17)
C2—C1—C6—C5	−1.5 (3)	C10—C9—C12—Cl2	−176.41 (15)
Cl1—C1—C6—C5	178.14 (15)	C8—C9—C12—Cl2	−0.7 (3)
C2—C1—C6—C7	179.61 (18)	C12—N3—C13—C18	−47.3 (3)
Cl1—C1—C6—C7	−0.8 (2)	N4—N3—C13—C18	140.74 (18)
N2—N1—C7—O1	172.09 (17)	C12—N3—C13—C14	132.67 (19)
N2—N1—C7—C6	−7.3 (3)	N4—N3—C13—C14	−39.3 (2)
C5—C6—C7—O1	−67.5 (3)	C18—C13—C14—C15	1.3 (3)
C1—C6—C7—O1	111.4 (2)	N3—C13—C14—C15	−178.65 (16)
C5—C6—C7—N1	111.9 (2)	C13—C14—C15—C16	−0.3 (3)
C1—C6—C7—N1	−69.2 (2)	C14—C15—C16—C17	−0.9 (3)
N1—N2—C8—C9	175.69 (16)	C15—C16—C17—C18	1.0 (3)
N2—C8—C9—C12	179.28 (18)	C14—C13—C18—C17	−1.2 (3)
N2—C8—C9—C10	−6.1 (3)	N3—C13—C18—C17	178.76 (18)
N3—N4—C10—C9	0.1 (2)	C16—C17—C18—C13	0.0 (3)
N3—N4—C10—C11	−179.09 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.03	2.874 (3)	168
C16—H16···Cl1ⁱⁱ	0.93	2.71	3.520 (4)	146
C18—H18···Cl2	0.93	2.83	3.237 (3)	108

Symmetry codes: (i) −x, −y+3, −z+1; (ii) x, −y+1, z−1/2.

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5-Chloro-4-[(2-chloro­benzoyl­hydrazono)methyl]-3-methyl-1-phenyl-1H-pyrazole

Supporting information

Key indicators

checkCIF/PLATON results

5-Chloro-4-[(2-chlorobenzoylhydrazono)methyl]-3-methyl-1-phenyl-1H-pyrazole