4-[(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methyl-idene-amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one.

In the mol-ecule of the title compound, C(22)H(20)ClN(5)O, the atoms of the two pyrazole rings and the -C=N- group which joins them are essentially coplanar, with an r.m.s. deviation of 0.054 (2) Å. The phenyl rings form dihedral angles of 41.24 (5) and 55.53 (5)° with this plane. The crystal structure is stabilized by weak inter-molecular π-π inter-actions, with centroid-to-centroid distances of 3.6179 (13) Å between the imidazole rings.

Related literature

For our previous work in this area, see: Zhu et al. (2005 ▶, 2010a ▶,b ▶,c ▶). For a related crystal structure, see: Shi et al. (2005 ▶).

Experimental

Crystal data

C22H20ClN5O

M = 405.88

Monoclinic,

a = 8.3982 (17) Å

b = 9.5204 (19) Å

c = 24.401 (5) Å

β = 97.24 (3)°

V = 1935.4 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 113 K

0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.957, T max = 0.978

15458 measured reflections

3397 independent reflections

2871 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.105

S = 1.08

3397 reflections

266 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); 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: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810039048/lh5137sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039048/lh5137Isup2.hkl

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

C22H20ClN5O	F(000) = 848
Mr = 405.88	Dx = 1.393 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4998 reflections
a = 8.3982 (17) Å	θ = 1.7–27.9°
b = 9.5204 (19) Å	µ = 0.22 mm−1
c = 24.401 (5) Å	T = 113 K
β = 97.24 (3)°	Block, pale yellow
V = 1935.4 (7) Å3	0.20 × 0.18 × 0.10 mm
Z = 4

Rigaku Saturn CCD diffractometer	3397 independent reflections
Radiation source: rotating anode	2871 reflections with I > 2σ(I)
confocal	Rint = 0.046
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 1.7°
ω and φ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −11→11
Tmin = 0.957, Tmax = 0.978	l = −29→29
15458 measured reflections

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0533P)2 + 0.6515P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
3397 reflections	Δρmax = 0.41 e Å−3
266 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: 0.0242 (16)

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	0.56582 (6)	0.05661 (6)	0.08916 (2)	0.02960 (19)
O1	0.75786 (16)	0.36105 (15)	−0.04914 (6)	0.0251 (4)
N1	0.80398 (18)	−0.09683 (17)	0.14372 (6)	0.0175 (4)
N2	0.96786 (17)	−0.11576 (16)	0.14899 (6)	0.0172 (4)
N3	1.03166 (18)	0.19175 (16)	0.02437 (6)	0.0181 (4)
N4	0.98109 (19)	0.45266 (17)	−0.08446 (6)	0.0196 (4)
N5	1.14617 (18)	0.42156 (17)	−0.07913 (6)	0.0201 (4)
C1	0.7142 (2)	−0.1746 (2)	0.17966 (8)	0.0181 (4)
C2	0.5695 (2)	−0.2379 (2)	0.16005 (8)	0.0206 (4)
H2	0.5247	−0.2262	0.1226	0.025*
C3	0.4910 (2)	−0.3182 (2)	0.19566 (9)	0.0246 (5)
H3	0.3912	−0.3610	0.1826	0.030*
C4	0.5566 (2)	−0.3368 (2)	0.25005 (9)	0.0263 (5)
H4	0.5026	−0.3927	0.2742	0.032*
C5	0.7015 (2)	−0.2736 (2)	0.26924 (8)	0.0254 (5)
H5	0.7469	−0.2867	0.3066	0.031*
C6	0.7808 (2)	−0.1913 (2)	0.23432 (8)	0.0213 (5)
H6	0.8794	−0.1468	0.2477	0.026*
C7	0.7592 (2)	0.0000 (2)	0.10393 (8)	0.0186 (4)
C8	0.8934 (2)	0.04644 (19)	0.08215 (8)	0.0164 (4)
C9	1.0207 (2)	−0.0306 (2)	0.11224 (7)	0.0163 (4)
C10	1.1952 (2)	−0.0254 (2)	0.10710 (8)	0.0209 (4)
H10A	1.2521	−0.0946	0.1321	0.031*
H10B	1.2366	0.0688	0.1168	0.031*
H10C	1.2119	−0.0470	0.0690	0.031*
C11	0.8978 (2)	0.14939 (19)	0.03858 (8)	0.0174 (4)
H11	0.8001	0.1860	0.0203	0.021*
C12	1.0353 (2)	0.2915 (2)	−0.01714 (8)	0.0178 (4)
C13	1.1767 (2)	0.3331 (2)	−0.03503 (7)	0.0189 (4)
C14	1.3431 (2)	0.2994 (2)	−0.01061 (8)	0.0265 (5)
H14A	1.4097	0.2833	−0.0402	0.040*
H14B	1.3425	0.2145	0.0121	0.040*
H14C	1.3871	0.3779	0.0124	0.040*
C15	0.9051 (2)	0.3662 (2)	−0.04929 (8)	0.0191 (4)
C16	1.2558 (2)	0.5346 (2)	−0.09045 (9)	0.0277 (5)
H16A	1.2703	0.5994	−0.0590	0.042*
H16B	1.2106	0.5856	−0.1237	0.042*
H16C	1.3598	0.4944	−0.0962	0.042*
C17	0.9040 (2)	0.5093 (2)	−0.13518 (8)	0.0194 (4)
C18	0.9457 (2)	0.4650 (2)	−0.18560 (8)	0.0231 (5)
H18	1.0276	0.3968	−0.1870	0.028*
C19	0.8665 (2)	0.5215 (2)	−0.23385 (8)	0.0257 (5)
H19	0.8960	0.4932	−0.2685	0.031*
C20	0.7448 (2)	0.6188 (2)	−0.23199 (8)	0.0250 (5)
H20	0.6897	0.6560	−0.2652	0.030*
C21	0.7038 (2)	0.6615 (2)	−0.18128 (9)	0.0256 (5)
H21	0.6198	0.7278	−0.1799	0.031*
C22	0.7844 (2)	0.6082 (2)	−0.13259 (8)	0.0235 (5)
H22	0.7578	0.6393	−0.0979	0.028*

	U11	U22	U33	U12	U13	U23
Cl1	0.0146 (3)	0.0348 (3)	0.0391 (3)	0.0050 (2)	0.0026 (2)	0.0133 (2)
O1	0.0202 (8)	0.0284 (8)	0.0269 (8)	0.0014 (6)	0.0035 (6)	0.0068 (6)
N1	0.0137 (8)	0.0208 (9)	0.0185 (8)	−0.0001 (7)	0.0033 (6)	0.0039 (7)
N2	0.0132 (8)	0.0197 (9)	0.0187 (8)	0.0005 (7)	0.0021 (6)	0.0010 (7)
N3	0.0204 (9)	0.0170 (9)	0.0169 (8)	−0.0018 (7)	0.0024 (7)	0.0003 (6)
N4	0.0204 (8)	0.0215 (9)	0.0171 (8)	0.0023 (7)	0.0031 (7)	0.0051 (7)
N5	0.0189 (9)	0.0227 (9)	0.0185 (8)	−0.0020 (7)	0.0012 (7)	0.0040 (7)
C1	0.0181 (10)	0.0162 (10)	0.0213 (10)	0.0016 (8)	0.0073 (8)	0.0021 (8)
C2	0.0198 (10)	0.0218 (11)	0.0209 (10)	0.0011 (8)	0.0049 (8)	−0.0013 (8)
C3	0.0223 (11)	0.0198 (11)	0.0330 (12)	−0.0023 (8)	0.0087 (9)	−0.0020 (9)
C4	0.0305 (12)	0.0190 (11)	0.0324 (12)	0.0012 (9)	0.0155 (10)	0.0055 (9)
C5	0.0308 (12)	0.0253 (12)	0.0213 (10)	0.0037 (9)	0.0075 (9)	0.0055 (9)
C6	0.0211 (10)	0.0213 (11)	0.0215 (10)	−0.0002 (8)	0.0028 (8)	0.0018 (8)
C7	0.0152 (10)	0.0192 (11)	0.0208 (10)	0.0022 (8)	0.0006 (8)	0.0016 (8)
C8	0.0154 (9)	0.0168 (10)	0.0166 (9)	−0.0007 (8)	0.0010 (8)	−0.0004 (8)
C9	0.0170 (9)	0.0172 (10)	0.0148 (9)	−0.0010 (8)	0.0024 (8)	−0.0014 (8)
C10	0.0158 (10)	0.0248 (11)	0.0220 (10)	0.0005 (8)	0.0030 (8)	0.0026 (8)
C11	0.0192 (10)	0.0160 (10)	0.0166 (10)	0.0021 (8)	0.0001 (8)	0.0021 (8)
C12	0.0218 (10)	0.0162 (10)	0.0154 (9)	−0.0008 (8)	0.0021 (8)	0.0000 (8)
C13	0.0239 (10)	0.0199 (11)	0.0127 (9)	−0.0014 (8)	0.0012 (8)	−0.0008 (8)
C14	0.0213 (11)	0.0367 (13)	0.0217 (11)	−0.0007 (9)	0.0035 (9)	0.0048 (9)
C15	0.0231 (11)	0.0174 (11)	0.0169 (10)	−0.0015 (8)	0.0028 (8)	−0.0001 (8)
C16	0.0283 (12)	0.0251 (12)	0.0305 (12)	−0.0043 (9)	0.0072 (9)	0.0051 (9)
C17	0.0233 (10)	0.0162 (10)	0.0182 (10)	−0.0040 (8)	0.0001 (8)	0.0033 (8)
C18	0.0275 (11)	0.0207 (11)	0.0215 (10)	0.0009 (9)	0.0054 (9)	0.0028 (8)
C19	0.0334 (12)	0.0276 (12)	0.0160 (10)	−0.0055 (10)	0.0030 (9)	0.0006 (9)
C20	0.0279 (11)	0.0231 (12)	0.0219 (10)	−0.0055 (9)	−0.0048 (9)	0.0046 (9)
C21	0.0239 (11)	0.0221 (11)	0.0293 (12)	0.0015 (9)	−0.0025 (9)	0.0016 (9)
C22	0.0277 (11)	0.0228 (11)	0.0198 (10)	−0.0011 (9)	0.0019 (9)	−0.0013 (8)

Cl1—C7	1.7064 (19)	C8—C11	1.450 (3)
O1—C15	1.238 (2)	C9—C10	1.487 (3)
N1—C7	1.357 (2)	C10—H10A	0.9800
N1—N2	1.378 (2)	C10—H10B	0.9800
N1—C1	1.433 (2)	C10—H10C	0.9800
N2—C9	1.326 (2)	C11—H11	0.9500
N3—C11	1.282 (2)	C12—C13	1.374 (3)
N3—C12	1.392 (2)	C12—C15	1.449 (3)
N4—C15	1.400 (2)	C13—C14	1.484 (3)
N4—N5	1.408 (2)	C14—H14A	0.9800
N4—C17	1.428 (2)	C14—H14B	0.9800
N5—C13	1.365 (2)	C14—H14C	0.9800
N5—C16	1.465 (3)	C16—H16A	0.9800
C1—C2	1.386 (3)	C16—H16B	0.9800
C1—C6	1.389 (3)	C16—H16C	0.9800
C2—C3	1.385 (3)	C17—C22	1.384 (3)
C2—H2	0.9500	C17—C18	1.387 (3)
C3—C4	1.383 (3)	C18—C19	1.385 (3)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.385 (3)	C19—C20	1.385 (3)
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.388 (3)	C20—C21	1.387 (3)
C5—H5	0.9500	C20—H20	0.9500
C6—H6	0.9500	C21—C22	1.387 (3)
C7—C8	1.378 (3)	C21—H21	0.9500
C8—C9	1.422 (3)	C22—H22	0.9500
C7—N1—N2	109.82 (14)	H10B—C10—H10C	109.5
C7—N1—C1	132.03 (16)	N3—C11—C8	121.01 (17)
N2—N1—C1	118.13 (15)	N3—C11—H11	119.5
C9—N2—N1	105.80 (15)	C8—C11—H11	119.5
C11—N3—C12	120.78 (16)	C13—C12—N3	121.80 (17)
C15—N4—N5	109.84 (15)	C13—C12—C15	108.06 (17)
C15—N4—C17	124.14 (16)	N3—C12—C15	130.13 (17)
N5—N4—C17	119.57 (15)	N5—C13—C12	110.13 (17)
C13—N5—N4	106.72 (14)	N5—C13—C14	121.60 (17)
C13—N5—C16	122.81 (16)	C12—C13—C14	128.17 (18)
N4—N5—C16	117.58 (15)	C13—C14—H14A	109.5
C2—C1—C6	120.76 (18)	C13—C14—H14B	109.5
C2—C1—N1	121.27 (17)	H14A—C14—H14B	109.5
C6—C1—N1	117.88 (17)	C13—C14—H14C	109.5
C3—C2—C1	119.28 (19)	H14A—C14—H14C	109.5
C3—C2—H2	120.4	H14B—C14—H14C	109.5
C1—C2—H2	120.4	O1—C15—N4	123.90 (17)
C4—C3—C2	120.61 (19)	O1—C15—C12	131.67 (18)
C4—C3—H3	119.7	N4—C15—C12	104.43 (16)
C2—C3—H3	119.7	N5—C16—H16A	109.5
C3—C4—C5	119.72 (19)	N5—C16—H16B	109.5
C3—C4—H4	120.1	H16A—C16—H16B	109.5
C5—C4—H4	120.1	N5—C16—H16C	109.5
C4—C5—C6	120.45 (19)	H16A—C16—H16C	109.5
C4—C5—H5	119.8	H16B—C16—H16C	109.5
C6—C5—H5	119.8	C22—C17—C18	120.90 (18)
C5—C6—C1	119.18 (18)	C22—C17—N4	118.02 (17)
C5—C6—H6	120.4	C18—C17—N4	121.07 (18)
C1—C6—H6	120.4	C19—C18—C17	119.21 (19)
N1—C7—C8	109.14 (16)	C19—C18—H18	120.4
N1—C7—Cl1	122.43 (14)	C17—C18—H18	120.4
C8—C7—Cl1	128.31 (15)	C20—C19—C18	120.59 (19)
C7—C8—C9	103.49 (16)	C20—C19—H19	119.7
C7—C8—C11	126.70 (17)	C18—C19—H19	119.7
C9—C8—C11	129.81 (17)	C19—C20—C21	119.54 (19)
N2—C9—C8	111.75 (16)	C19—C20—H20	120.2
N2—C9—C10	119.64 (17)	C21—C20—H20	120.2
C8—C9—C10	128.61 (17)	C20—C21—C22	120.50 (19)
C9—C10—H10A	109.5	C20—C21—H21	119.8
C9—C10—H10B	109.5	C22—C21—H21	119.8
H10A—C10—H10B	109.5	C17—C22—C21	119.24 (19)
C9—C10—H10C	109.5	C17—C22—H22	120.4
H10A—C10—H10C	109.5	C21—C22—H22	120.4
C7—N1—N2—C9	−0.2 (2)	C7—C8—C11—N3	175.01 (19)
C1—N1—N2—C9	−178.74 (16)	C9—C8—C11—N3	−5.4 (3)
C15—N4—N5—C13	−9.4 (2)	C11—N3—C12—C13	−176.57 (18)
C17—N4—N5—C13	−162.32 (16)	C11—N3—C12—C15	2.0 (3)
C15—N4—N5—C16	−152.04 (17)	N4—N5—C13—C12	8.4 (2)
C17—N4—N5—C16	55.0 (2)	C16—N5—C13—C12	148.65 (18)
C7—N1—C1—C2	44.7 (3)	N4—N5—C13—C14	−168.34 (17)
N2—N1—C1—C2	−137.15 (18)	C16—N5—C13—C14	−28.1 (3)
C7—N1—C1—C6	−138.7 (2)	N3—C12—C13—N5	174.47 (16)
N2—N1—C1—C6	39.5 (2)	C15—C12—C13—N5	−4.4 (2)
C6—C1—C2—C3	0.1 (3)	N3—C12—C13—C14	−9.1 (3)
N1—C1—C2—C3	176.61 (17)	C15—C12—C13—C14	172.05 (19)
C1—C2—C3—C4	−0.7 (3)	N5—N4—C15—O1	−172.85 (17)
C2—C3—C4—C5	0.5 (3)	C17—N4—C15—O1	−21.4 (3)
C3—C4—C5—C6	0.3 (3)	N5—N4—C15—C12	6.6 (2)
C4—C5—C6—C1	−0.9 (3)	C17—N4—C15—C12	158.02 (17)
C2—C1—C6—C5	0.7 (3)	C13—C12—C15—O1	177.9 (2)
N1—C1—C6—C5	−175.93 (17)	N3—C12—C15—O1	−0.8 (4)
N2—N1—C7—C8	0.1 (2)	C13—C12—C15—N4	−1.4 (2)
C1—N1—C7—C8	178.39 (18)	N3—C12—C15—N4	179.85 (18)
N2—N1—C7—Cl1	−176.18 (13)	C15—N4—C17—C22	67.4 (3)
C1—N1—C7—Cl1	2.1 (3)	N5—N4—C17—C22	−143.73 (18)
N1—C7—C8—C9	0.0 (2)	C15—N4—C17—C18	−111.6 (2)
Cl1—C7—C8—C9	176.01 (15)	N5—N4—C17—C18	37.3 (3)
N1—C7—C8—C11	179.71 (17)	C22—C17—C18—C19	0.3 (3)
Cl1—C7—C8—C11	−4.3 (3)	N4—C17—C18—C19	179.23 (18)
N1—N2—C9—C8	0.2 (2)	C17—C18—C19—C20	−1.4 (3)
N1—N2—C9—C10	−179.94 (16)	C18—C19—C20—C21	1.0 (3)
C7—C8—C9—N2	−0.1 (2)	C19—C20—C21—C22	0.4 (3)
C11—C8—C9—N2	−179.82 (18)	C18—C17—C22—C21	1.1 (3)
C7—C8—C9—C10	−179.97 (19)	N4—C17—C22—C21	−177.85 (17)
C11—C8—C9—C10	0.3 (3)	C20—C21—C22—C17	−1.5 (3)
C12—N3—C11—C8	−179.42 (16)