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

Zhu, H.; Zhu, J.; Ban, L.; Zhang, P.; Zhang, M.

doi:10.1107/S1600536810039048

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2724

https://doi.org/10.1107/S1600536810039048

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

Hualing Zhu,^a ^* Jinhua Zhu,^b Litong Ban,^c Pingping Zhang ^d and Miao Zhang ^a

^aDepartment of Basic Science, Tianjin Agricultural College, Tianjin Jinjing Road No. 22, Tianjin 300384, People's Republic of China, ^bService Center of Meteorological Science and Technology of Shanxi Province, Taiyuan Xinjian Road No. 152, Taiyuan, Shanxi 030002, People's Republic of China, ^cDepartment of Agricultural Science, Tianjin Agricultural College, Tianjin Jinjing Road No. 22, Tianjin 300384, People's Republic of China, and ^dDepartment of Food Science, Tianjin Agricultural College, Tianjin Jinjing Road No. 22, Tianjin 300384, People's Republic of China
^*Correspondence e-mail: zhuhualing2004@126.com

(Received 24 September 2010; accepted 29 September 2010; online 9 October 2010)

In the molecule of the title compound, C₂₂H₂₀ClN₅O, 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 intermolecular π–π interactions, 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_r = 405.88
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.105
S = 1.08
3397 reflections
266 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −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).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039048/lh5137Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies (Zhu et al., 2005, 2010a,b,c) of pyrazolone derivatives as potential ligands (Shi et al., 2005) we report the crystal structure of the title compound (I).

The molecular structure of the title compound is shown in Fig. 1. Atoms C11 and N3 and the two pyrazole rings are essentially coplplanar with the largest deviation being 0.0543 (18) Å for atom C13. The crystal structure is stabilized by weak intermolecular π–π interactions with ring centroid to ring centroid distances of 3.6179 (13) Å between the imidazole rings (see Fig. 2).

Related literature top

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 top

The title compound was synthesized by refluxing a mixture of 4-formacyl-5-methyl-3-chloro-2-phenyl-2H-pyrazole (15m mol) and 4-antipyrine (15 mmol) in ethanol (100 ml) over a steam bath for about 4 h. The solution was then cooled to room temperature. After one day, pale-yellow blocks wre obtained and they were dried in air. Recrystallization of a solution of the title compound in ethanol afforded pale-yellow crystals suitable for X-ray analysis.

Structure description top

As part of our ongoing studies (Zhu et al., 2005, 2010a,b,c) of pyrazolone derivatives as potential ligands (Shi et al., 2005) we report the crystal structure of the title compound (I).

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).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. Part of the crystal structure showing intermolecular π–π interactions as dashed lines.

4-[(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylideneamino]- 1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one top

Crystal data top

C₂₂H₂₀ClN₅O	F(000) = 848
M_r = 405.88	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0533P)² + 0.6515P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
3397 reflections	Δρ_max = 0.41 e Å⁻³
266 parameters	Δρ_min = −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)

Crystal data top

C₂₂H₂₀ClN₅O	V = 1935.4 (7) Å³
M_r = 405.88	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.3982 (17) Å	µ = 0.22 mm⁻¹
b = 9.5204 (19) Å	T = 113 K
c = 24.401 (5) Å	0.20 × 0.18 × 0.10 mm
β = 97.24 (3)°

Data collection top

Rigaku Saturn CCD diffractometer	3397 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	2871 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.978	R_int = 0.046
15458 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.08	Δρ_max = 0.41 e Å⁻³
3397 reflections	Δρ_min = −0.25 e Å⁻³
266 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	0.56582 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀ClN₅O
M_r	405.88
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	8.3982 (17), 9.5204 (19), 24.401 (5)
β (°)	97.24 (3)
V (Å³)	1935.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.20 × 0.18 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2008)
T_min, T_max	0.957, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	15458, 3397, 2871
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.105, 1.08
No. of reflections	3397
No. of parameters	266
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.25

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the Science Development Committee of Tianjin Agricultural College for partial funding (research grant No. 2007029)

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, J. M., Zhang, F. X., Wu, C. J. & Liu, L. D. (2005). Acta Cryst. E61, m2320–m2321. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhu, H., Shi, J., Wei, Z., Bai, Y. & Bu, L. (2010a). Acta Cryst. E66, o1583. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhu, H., Shi, J., Wei, Z., Dai, R. & Zhang, X. (2010b). Acta Cryst. E66, o1352. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhu, H., Wei, Z., Bu, L., Xu, X. & Shi, J. (2010c). Acta Cryst. E66, m904. Web of Science CrossRef IUCr Journals Google Scholar
Zhu, H., Zhang, X., Song, Y., Xu, H. & Dong, M. (2005). Acta Cryst. E61, o2387–o2388. Web of Science CSD CrossRef IUCr Journals Google Scholar

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