5-(4-Chloro-phen-yl)-1-(2,4-dichloro-phen-yl)-4-methyl-N-(3-pyridylmeth-yl)-1H-pyrazole-3-carboxamide.

In the title compound, C(23)H(17)Cl(3)N(4)O, the benzene rings are oriented with respect to the pyrazole ring at dihedral angles of 39.9 (2) and 72.90 (13)° for the chloro-phenyl and di-chloro-phenyl rings, respectively. Inter-molecular C-H⋯N and C-H⋯Cl inter-actions 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 = 471.76

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.06

4914 reflections

285 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.75 e Å−3

Δρmin = −0.38 e Å−3

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 ▶).

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

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

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

C23H17Cl3N4O	F(000) = 968
Mr = 471.76	Dx = 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

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

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(Fo2) + (0.0441P)2 + 0.5347P] where P = (Fo2 + 2Fc2)/3
4914 reflections	(Δ/σ)max = 0.002
285 parameters	Δρmax = 0.75 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .