5-(4-Chloro­phen­yl)-1-(2,4-dichloro­phen­yl)-4-methyl-N-(3-pyridylmeth­yl)-1H-pyrazole-3-carboxamide

He, X.; Zhong, W.; Xiao, J.; Zheng, Z.; Li, S.

doi:10.1107/S1600536809013609

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1077

doi:10.1107/S1600536809013609

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5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(3-pyridylmethyl)-1H-pyrazole-3-carboxamide

Xinhua He,^a Wu Zhong,^a Junhai Xiao,^a Zhibing Zheng ^a ^* and Song Li ^a

^aBeijing Institute of Pharmacology and Toxicology, Beijing 100850, People's Republic of China
^*Correspondence e-mail: hexinhua01@126.com

(Received 30 December 2008; accepted 10 April 2009; online 18 April 2009)

In the title compound, C₂₃H₁₇Cl₃N₄O, the benzene rings are oriented with respect to the pyrazole ring at dihedral angles of 39.9 (2) and 72.90 (13)° for the chlorophenyl and dichlorophenyl rings, respectively. Intermolecular C—H⋯N and C—H⋯Cl interactions are observed in the crystal packing.

Related literature

For general background to pyrazole derivatives and their biological activity, see: Srivastava et al. (2008 ); LoVerme et al. (2009 ); Rinaldi-Carmona et al. (1994 ). For the synthesis, see: Li et al. (2007 ).

Experimental

Crystal data

C₂₃H₁₇Cl₃N₄O
M_r = 471.76
Monoclinic, P 2₁ /c
a = 9.0032 (4) Å
b = 20.1001 (8) Å
c = 11.4664 (5) Å
β = 92.003 (2)°
V = 2073.75 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 113 K
0.26 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.888, T_max = 0.921
19184 measured reflections
4914 independent reflections
4152 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.085
S = 1.06
4914 reflections
285 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯N4ⁱ	0.95	2.56	3.272 (2)	132
C7—H7⋯Cl2ⁱⁱ	0.95	2.84	3.5903 (15)	137
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2004 ) and publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013609/ez2158sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013609/ez2158Isup2.hkl

checkCIF report

Comment top

Pyrazole derivatives have been found to be a novel class of cannabinoid CB1 receptor antagonists (Srivastava et al., 2008; LoVerme et al., 2009; Rinaldi-Carmona M. et al., 1994). The crystal structure of the title compound (IC50 =0.139nM at CB1) was analyzed by X-ray diffraction, for the purpose of studying its quantitative structure-activity relationship (QSAR).

In the molecule of the title compound (Fig. 1) the bond lengths and angles are generally within normal ranges. The benzene rings (C6—C11) and (C12—C17) are oriented at dihedral angles of 39.9 (2)° and 72.90 (13)°, respectively, with respect to the pyrazole ring.

In the crystal structure, the molecules are linked by intermolecular C17—H17···N4 and C7—H7···Cl2 interactions (Fig. 2).

Related literature top

For general background to pyrazole derivatives and their biological activity, see: Srivastava et al. (2008) ; LoVerme et al. (2009); Rinaldi-Carmona et al. (1994). For the synthesis, see: Li et al. (2007).

Experimental top

The title compound was synthesized according to the procedure of Li et al.(2007). Colorless single crystals were obtained by slow evaporation of a solution in ehtyl acetate.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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: CrystalStructure (Rigaku/MSC, 2004) and publCIF (Westrip, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atom-numbering scheme and ellipsoids at the 30 % probability level.
	Fig. 2. The crystal packing of the title compound. Hydrogen bonds are indicated by dashed lines.

5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(3-pyridylmethyl)- 1H-pyrazole-3-carboxamide top

Crystal data top

C₂₃H₁₇Cl₃N₄O	F(000) = 968
M_r = 471.76	D_x = 1.511 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71070 Å
a = 9.0032 (4) Å	Cell parameters from 4274 reflections
b = 20.1001 (8) Å	θ = 1.8–27.9°
c = 11.4664 (5) Å	µ = 0.47 mm⁻¹
β = 92.003 (2)°	T = 113 K
V = 2073.75 (15) Å³	Block, colorless
Z = 4	0.26 × 0.20 × 0.18 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4914 independent reflections
Radiation source: rotating anode	4152 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.034
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.0°
ω and ϕ scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −26→26
T_min = 0.888, T_max = 0.921	l = −15→15
19184 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0441P)² + 0.5347P] where P = (F_o² + 2F_c²)/3
4914 reflections	(Δ/σ)_max = 0.002
285 parameters	Δρ_max = 0.75 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₃H₁₇Cl₃N₄O	V = 2073.75 (15) Å³
M_r = 471.76	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0032 (4) Å	µ = 0.47 mm⁻¹
b = 20.1001 (8) Å	T = 113 K
c = 11.4664 (5) Å	0.26 × 0.20 × 0.18 mm
β = 92.003 (2)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4914 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	4152 reflections with I > 2σ(I)
T_min = 0.888, T_max = 0.921	R_int = 0.034
19184 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.75 e Å⁻³
4914 reflections	Δρ_min = −0.38 e Å⁻³
285 parameters

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	0.01811 (4)	0.643967 (18)	0.56112 (3)	0.02233 (10)
Cl2	0.52709 (4)	0.554267 (18)	0.22278 (3)	0.02014 (10)
Cl3	0.15192 (4)	0.596113 (19)	−0.14473 (3)	0.02088 (10)
O1	0.60926 (12)	0.24050 (6)	0.40372 (10)	0.0235 (3)
N1	0.65174 (14)	0.25624 (6)	0.21143 (12)	0.0177 (3)
H1	0.633 (2)	0.2770 (10)	0.1553 (17)	0.023 (5)*
N2	0.47501 (14)	0.36428 (6)	0.20324 (11)	0.0158 (3)
N3	0.38825 (14)	0.41730 (6)	0.22738 (11)	0.0149 (3)
N4	1.09010 (16)	0.18709 (7)	0.40063 (13)	0.0255 (3)
C1	0.59001 (16)	0.27258 (7)	0.31272 (14)	0.0160 (3)
C2	0.49452 (15)	0.33347 (7)	0.30626 (13)	0.0145 (3)
C3	0.41906 (16)	0.36537 (7)	0.39652 (13)	0.0142 (3)
C4	0.35219 (16)	0.42006 (7)	0.34305 (13)	0.0138 (3)
C5	0.40835 (18)	0.34400 (8)	0.52139 (13)	0.0203 (3)
H5A	0.4938	0.3614	0.5672	0.030*
H5B	0.4080	0.2953	0.5256	0.030*
H5C	0.3163	0.3614	0.5529	0.030*
C6	0.26488 (16)	0.47476 (7)	0.39330 (12)	0.0135 (3)
C7	0.30933 (16)	0.49932 (8)	0.50303 (13)	0.0159 (3)
H7	0.3927	0.4800	0.5432	0.019*
C8	0.23420 (17)	0.55137 (7)	0.55469 (13)	0.0169 (3)
H8	0.2662	0.5679	0.6290	0.020*
C9	0.11196 (16)	0.57867 (7)	0.49587 (13)	0.0155 (3)
C10	0.06310 (16)	0.55496 (7)	0.38774 (13)	0.0155 (3)
H10	−0.0215	0.5740	0.3488	0.019*
C11	0.13936 (16)	0.50292 (7)	0.33683 (13)	0.0144 (3)
H11	0.1060	0.4863	0.2629	0.017*
C12	0.33945 (16)	0.45989 (7)	0.13373 (12)	0.0143 (3)
C13	0.39214 (16)	0.52489 (7)	0.12519 (13)	0.0144 (3)
C14	0.33693 (16)	0.56739 (7)	0.03826 (13)	0.0154 (3)
H14	0.3721	0.6118	0.0325	0.019*
C15	0.22900 (16)	0.54305 (7)	−0.03979 (12)	0.0155 (3)
C16	0.17985 (17)	0.47747 (7)	−0.03588 (13)	0.0181 (3)
H16	0.1090	0.4613	−0.0923	0.022*
C17	0.23618 (17)	0.43610 (8)	0.05187 (13)	0.0172 (3)
H17	0.2037	0.3912	0.0557	0.021*
C18	0.74791 (16)	0.19856 (7)	0.19942 (14)	0.0185 (3)
H18A	0.7511	0.1867	0.1158	0.022*
H18B	0.7040	0.1605	0.2408	0.022*
C19	0.95085 (18)	0.18300 (8)	0.35444 (15)	0.0213 (3)
H19	0.8786	0.1607	0.3985	0.026*
C20	0.90543 (16)	0.20918 (7)	0.24668 (13)	0.0158 (3)
C21	1.01070 (18)	0.24347 (8)	0.18393 (14)	0.0200 (3)
H21	0.9844	0.2630	0.1106	0.024*
C22	1.15446 (18)	0.24873 (8)	0.23013 (15)	0.0237 (3)
H22	1.2281	0.2721	0.1892	0.028*
C23	1.18931 (18)	0.21935 (8)	0.33690 (16)	0.0254 (4)
H23	1.2889	0.2222	0.3666	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0286 (2)	0.01416 (17)	0.0247 (2)	0.00408 (14)	0.00882 (16)	−0.00229 (14)
Cl2	0.01844 (19)	0.02230 (19)	0.01936 (19)	−0.00254 (14)	−0.00415 (14)	−0.00143 (14)
Cl3	0.0230 (2)	0.02238 (19)	0.01701 (19)	0.00224 (15)	−0.00231 (14)	0.00519 (14)
O1	0.0245 (6)	0.0209 (6)	0.0252 (6)	0.0074 (5)	0.0007 (5)	0.0043 (5)
N1	0.0171 (6)	0.0151 (6)	0.0208 (7)	0.0055 (5)	−0.0006 (5)	0.0016 (5)
N2	0.0145 (6)	0.0130 (6)	0.0199 (7)	0.0034 (5)	0.0021 (5)	−0.0005 (5)
N3	0.0163 (6)	0.0135 (6)	0.0151 (6)	0.0048 (5)	0.0021 (5)	0.0009 (5)
N4	0.0232 (7)	0.0239 (7)	0.0290 (8)	0.0020 (6)	−0.0049 (6)	0.0042 (6)
C1	0.0110 (7)	0.0131 (7)	0.0239 (8)	−0.0007 (5)	−0.0010 (6)	−0.0006 (6)
C2	0.0108 (7)	0.0132 (6)	0.0194 (7)	−0.0009 (5)	−0.0002 (5)	0.0004 (6)
C3	0.0113 (7)	0.0139 (7)	0.0172 (7)	−0.0002 (5)	−0.0016 (5)	0.0003 (5)
C4	0.0127 (7)	0.0150 (7)	0.0136 (7)	−0.0003 (5)	0.0001 (5)	−0.0006 (5)
C5	0.0229 (8)	0.0208 (8)	0.0170 (8)	0.0047 (6)	−0.0015 (6)	0.0028 (6)
C6	0.0126 (7)	0.0136 (7)	0.0144 (7)	−0.0001 (5)	0.0024 (5)	0.0010 (5)
C7	0.0124 (7)	0.0202 (7)	0.0151 (7)	−0.0006 (6)	0.0000 (5)	0.0007 (6)
C8	0.0166 (7)	0.0186 (7)	0.0154 (7)	−0.0036 (6)	0.0016 (6)	−0.0025 (6)
C9	0.0165 (7)	0.0103 (6)	0.0201 (8)	−0.0010 (5)	0.0075 (6)	−0.0006 (5)
C10	0.0137 (7)	0.0139 (7)	0.0190 (7)	0.0010 (5)	0.0020 (6)	0.0033 (6)
C11	0.0148 (7)	0.0146 (7)	0.0139 (7)	−0.0006 (5)	0.0004 (5)	0.0004 (5)
C12	0.0156 (7)	0.0149 (7)	0.0128 (7)	0.0050 (5)	0.0037 (6)	0.0011 (5)
C13	0.0123 (7)	0.0173 (7)	0.0138 (7)	0.0017 (5)	0.0017 (5)	−0.0028 (5)
C14	0.0170 (7)	0.0142 (7)	0.0153 (7)	0.0006 (5)	0.0034 (6)	0.0002 (6)
C15	0.0168 (7)	0.0171 (7)	0.0127 (7)	0.0039 (6)	0.0024 (6)	0.0017 (6)
C16	0.0188 (7)	0.0198 (7)	0.0157 (7)	−0.0001 (6)	−0.0011 (6)	−0.0019 (6)
C17	0.0188 (7)	0.0142 (7)	0.0188 (8)	0.0004 (6)	0.0023 (6)	−0.0020 (6)
C18	0.0152 (7)	0.0142 (7)	0.0262 (8)	0.0031 (6)	−0.0004 (6)	−0.0041 (6)
C19	0.0194 (8)	0.0181 (7)	0.0265 (8)	−0.0005 (6)	0.0015 (6)	0.0041 (6)
C20	0.0154 (7)	0.0110 (6)	0.0212 (8)	0.0033 (5)	0.0012 (6)	−0.0037 (6)
C21	0.0238 (8)	0.0174 (7)	0.0190 (8)	0.0003 (6)	0.0029 (6)	−0.0015 (6)
C22	0.0198 (8)	0.0235 (8)	0.0284 (9)	−0.0049 (6)	0.0073 (7)	−0.0030 (7)
C23	0.0168 (8)	0.0247 (8)	0.0344 (10)	0.0002 (6)	−0.0033 (7)	−0.0044 (7)

Geometric parameters (Å, º) top

Cl1—C9	1.7437 (15)	C8—H8	0.9500
Cl2—C13	1.7268 (15)	C9—C10	1.386 (2)
Cl3—C15	1.7346 (15)	C10—C11	1.391 (2)
O1—C1	1.2336 (19)	C10—H10	0.9500
N1—C1	1.346 (2)	C11—H11	0.9500
N1—C18	1.4565 (18)	C12—C17	1.383 (2)
N1—H1	0.78 (2)	C12—C13	1.395 (2)
N2—C2	1.3399 (19)	C13—C14	1.391 (2)
N2—N3	1.3556 (16)	C14—C15	1.387 (2)
N3—C4	1.3776 (19)	C14—H14	0.9500
N3—C12	1.4303 (18)	C15—C16	1.392 (2)
N4—C23	1.341 (2)	C16—C17	1.388 (2)
N4—C19	1.346 (2)	C16—H16	0.9500
C1—C2	1.496 (2)	C17—H17	0.9500
C2—C3	1.412 (2)	C18—C20	1.515 (2)
C3—C4	1.386 (2)	C18—H18A	0.9900
C3—C5	1.501 (2)	C18—H18B	0.9900
C4—C6	1.480 (2)	C19—C20	1.391 (2)
C5—H5A	0.9800	C19—H19	0.9500
C5—H5B	0.9800	C20—C21	1.392 (2)
C5—H5C	0.9800	C21—C22	1.385 (2)
C6—C7	1.397 (2)	C21—H21	0.9500
C6—C11	1.4019 (19)	C22—C23	1.385 (2)
C7—C8	1.390 (2)	C22—H22	0.9500
C7—H7	0.9500	C23—H23	0.9500
C8—C9	1.384 (2)

C1—N1—C18	122.73 (14)	C10—C11—H11	119.6
C1—N1—H1	119.9 (14)	C6—C11—H11	119.6
C18—N1—H1	117.3 (14)	C17—C12—C13	119.89 (13)
C2—N2—N3	104.00 (12)	C17—C12—N3	118.96 (13)
N2—N3—C4	112.65 (12)	C13—C12—N3	121.14 (13)
N2—N3—C12	118.77 (12)	C14—C13—C12	120.77 (13)
C4—N3—C12	128.47 (12)	C14—C13—Cl2	118.68 (11)
C23—N4—C19	116.36 (15)	C12—C13—Cl2	120.55 (11)
O1—C1—N1	123.54 (14)	C15—C14—C13	118.06 (13)
O1—C1—C2	122.20 (14)	C15—C14—H14	121.0
N1—C1—C2	114.26 (13)	C13—C14—H14	121.0
N2—C2—C3	112.63 (13)	C14—C15—C16	121.99 (13)
N2—C2—C1	118.63 (13)	C14—C15—Cl3	119.01 (11)
C3—C2—C1	128.74 (13)	C16—C15—Cl3	119.00 (12)
C4—C3—C2	104.40 (13)	C17—C16—C15	118.84 (14)
C4—C3—C5	127.40 (13)	C17—C16—H16	120.6
C2—C3—C5	128.16 (13)	C15—C16—H16	120.6
N3—C4—C3	106.29 (13)	C12—C17—C16	120.33 (14)
N3—C4—C6	123.44 (13)	C12—C17—H17	119.8
C3—C4—C6	130.20 (13)	C16—C17—H17	119.8
C3—C5—H5A	109.5	N1—C18—C20	113.96 (12)
C3—C5—H5B	109.5	N1—C18—H18A	108.8
H5A—C5—H5B	109.5	C20—C18—H18A	108.8
C3—C5—H5C	109.5	N1—C18—H18B	108.8
H5A—C5—H5C	109.5	C20—C18—H18B	108.8
H5B—C5—H5C	109.5	H18A—C18—H18B	107.7
C7—C6—C11	118.31 (13)	N4—C19—C20	124.54 (15)
C7—C6—C4	118.28 (13)	N4—C19—H19	117.7
C11—C6—C4	123.41 (13)	C20—C19—H19	117.7
C8—C7—C6	121.43 (14)	C19—C20—C21	117.51 (14)
C8—C7—H7	119.3	C19—C20—C18	120.44 (14)
C6—C7—H7	119.3	C21—C20—C18	122.03 (14)
C9—C8—C7	118.78 (14)	C22—C21—C20	118.94 (15)
C9—C8—H8	120.6	C22—C21—H21	120.5
C7—C8—H8	120.6	C20—C21—H21	120.5
C8—C9—C10	121.46 (13)	C21—C22—C23	119.02 (15)
C8—C9—Cl1	118.58 (12)	C21—C22—H22	120.5
C10—C9—Cl1	119.96 (11)	C23—C22—H22	120.5
C9—C10—C11	119.23 (13)	N4—C23—C22	123.58 (15)
C9—C10—H10	120.4	N4—C23—H23	118.2
C11—C10—H10	120.4	C22—C23—H23	118.2
C10—C11—C6	120.77 (13)

C2—N2—N3—C4	−0.44 (16)	Cl1—C9—C10—C11	179.90 (11)
C2—N2—N3—C12	−177.01 (12)	C9—C10—C11—C6	−0.4 (2)
C18—N1—C1—O1	0.1 (2)	C7—C6—C11—C10	1.4 (2)
C18—N1—C1—C2	−179.79 (13)	C4—C6—C11—C10	−179.03 (14)
N3—N2—C2—C3	1.05 (16)	N2—N3—C12—C17	69.79 (18)
N3—N2—C2—C1	−178.45 (12)	C4—N3—C12—C17	−106.16 (17)
O1—C1—C2—N2	−177.73 (14)	N2—N3—C12—C13	−111.38 (15)
N1—C1—C2—N2	2.13 (19)	C4—N3—C12—C13	72.7 (2)
O1—C1—C2—C3	2.9 (2)	C17—C12—C13—C14	3.0 (2)
N1—C1—C2—C3	−177.28 (14)	N3—C12—C13—C14	−175.77 (13)
N2—C2—C3—C4	−1.25 (16)	C17—C12—C13—Cl2	−177.12 (11)
C1—C2—C3—C4	178.18 (14)	N3—C12—C13—Cl2	4.06 (19)
N2—C2—C3—C5	176.76 (14)	C12—C13—C14—C15	−0.4 (2)
C1—C2—C3—C5	−3.8 (2)	Cl2—C13—C14—C15	179.75 (11)
N2—N3—C4—C3	−0.31 (16)	C13—C14—C15—C16	−2.5 (2)
C12—N3—C4—C3	175.84 (14)	C13—C14—C15—Cl3	176.98 (11)
N2—N3—C4—C6	176.89 (13)	C14—C15—C16—C17	2.8 (2)
C12—N3—C4—C6	−7.0 (2)	Cl3—C15—C16—C17	−176.73 (11)
C2—C3—C4—N3	0.89 (15)	C13—C12—C17—C16	−2.8 (2)
C5—C3—C4—N3	−177.14 (14)	N3—C12—C17—C16	176.05 (13)
C2—C3—C4—C6	−176.05 (14)	C15—C16—C17—C12	−0.1 (2)
C5—C3—C4—C6	5.9 (3)	C1—N1—C18—C20	−78.52 (18)
N3—C4—C6—C7	−138.52 (15)	C23—N4—C19—C20	0.6 (2)
C3—C4—C6—C7	38.0 (2)	N4—C19—C20—C21	−1.8 (2)
N3—C4—C6—C11	41.9 (2)	N4—C19—C20—C18	176.56 (15)
C3—C4—C6—C11	−141.62 (16)	N1—C18—C20—C19	102.36 (17)
C11—C6—C7—C8	−1.5 (2)	N1—C18—C20—C21	−79.37 (18)
C4—C6—C7—C8	178.89 (13)	C19—C20—C21—C22	1.2 (2)
C6—C7—C8—C9	0.6 (2)	C18—C20—C21—C22	−177.11 (14)
C7—C8—C9—C10	0.4 (2)	C20—C21—C22—C23	0.4 (2)
C7—C8—C9—Cl1	180.00 (11)	C19—N4—C23—C22	1.3 (3)
C8—C9—C10—C11	−0.5 (2)	C21—C22—C23—N4	−1.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N4ⁱ	0.95	2.56	3.272 (2)	132
C7—H7···Cl2ⁱⁱ	0.95	2.84	3.5903 (15)	137

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇Cl₃N₄O
M_r	471.76
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	9.0032 (4), 20.1001 (8), 11.4664 (5)
β (°)	92.003 (2)
V (Å³)	2073.75 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.26 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.888, 0.921
No. of measured, independent and observed [I > 2σ(I)] reflections	19184, 4914, 4152
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.085, 1.06
No. of reflections	4914
No. of parameters	285
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.38

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2004) and publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N4ⁱ	0.95	2.56	3.272 (2)	131.9
C7—H7···Cl2ⁱⁱ	0.95	2.839	3.5903 (15)	136.7

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

Acknowledgements

We thank T. L. Liang for her fruitful help.

References

Li, S., Liu, M. J. & Zheng, Z. B. (2007). WO Patent WO2007079681. Google Scholar
LoVerme, J., Duranti, A., Tontini, A., Spadoni, G., Mor, M., Rivara, S., Stella, N., Xu, C., Tarzia, G. & Piomelli, D. (2009). Bioorg. Med. Chem. Lett. 19, 639–643. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Rinaldi-Carmona, M., Barth, F., Héaulme, M., Shire, D., Calandra, B., Congy, C., Martinez, S., Maruani, J., Néliat, G., Caput, D., Ferrara, P., Soubrié, P., Breliére, J. C. & LeFur, G. (1994). FEBS Lett. 350, 240–244. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Srivastava, B. K., et al. (2008). Bioorg. Med. Chem. Lett. 18, 963–968. Web of Science CrossRef PubMed CAS Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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Volume 65| Part 5| May 2009| Page o1077

doi:10.1107/S1600536809013609

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5-(4-Chloro­phen­yl)-1-(2,4-di­chloro­phen­yl)-4-methyl-N-(3-pyridylmeth­yl)-1H-pyrazole-3-carboxamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(3-pyridylmethyl)-1H-pyrazole-3-carboxamide