2-(4-Chloro­phen­yl)-5-(3,4-dimethoxy­pheneth­yl)-6,7-dihydro­pyrazolo[1,5-a]pyrazin-4(5H)-one

Zhang, J.-H.; Zuo, H.; Xie, Y.-S.; Zhao, B.-X.

doi:10.1107/S1600536809020212

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1457

doi:10.1107/S1600536809020212

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2-(4-Chlorophenyl)-5-(3,4-dimethoxyphenethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one

Jin-Hua Zhang,^a Hua Zuo,^b Yong-Sheng Xie ^a and Bao-Xiang Zhao ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China, and ^bCollege of Pharmaceutical Sciences, Southwest University, Chongqing 400716, People's Republic of China
^*Correspondence e-mail: bxzhao@sdu.edu.cn

(Received 15 May 2009; accepted 27 May 2009; online 6 June 2009)

In the title compound, C₂₂H₂₂ClN₃O₃, the dihedral angles between the planes of the benzene rings and the pyrazole ring are 16.05 (10) and 84.84 (10)°. The conformation of the six-membered heterocyclic ring is close to a screw-boat. The crystal packing is stabilized by weak intermolecular C—H⋯O interactions and is also consolidated by C—H⋯π interactions.

Related literature

For the bioactivity of pyrazole derivatives, see: Farag et al. (2008 ); Pan et al. (2008 ); Szabó et al. (2008 ); Xie et al. (2008 ). For a related structure, see: Zhang et al. (2008 ).

Experimental

Crystal data

C₂₂H₂₂ClN₃O₃
M_r = 411.88
Triclinic, $[P \overline 1]$
a = 7.1709 (4) Å
b = 10.6982 (5) Å
c = 13.9169 (6) Å
α = 81.156 (3)°
β = 77.150 (2)°
γ = 72.278 (2)°
V = 987.25 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.40 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2005 ) T_min = 0.916, T_max = 0.978
8654 measured reflections
3999 independent reflections
2969 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.115
S = 1.03
3999 reflections
326 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.92 (2)	2.48 (2)	3.341 (2)	156.3 (17)
C8—H8⋯O1ⁱ	0.94 (2)	2.39 (2)	3.296 (2)	161.4 (19)
C11—H11B⋯Cg1ⁱⁱ	0.99 (2)	2.67 (2)	3.413 (2)	132.2 (16)
C12—H12A⋯Cg2ⁱⁱⁱ	1.00 (3)	2.77 (2)	3.640 (2)	146.2 (17)
Symmetry codes: (i) -x-1, -y+2, -z; (ii) -x-2, -y+1, -z; (iii) x-1, y, z. Cg1 and Cg2 are centroids of the C15–C20 and C1–C6 rings, respectively.

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020212/pv2160sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020212/pv2160Isup2.hkl

checkCIF report

Comment top

Many pyrazole derivatives are known to exhibit a wide range of biological properties (Farag et al., 2008; Szabó et al., 2008). As part of our continuing project on the study of the interactions occurring between small molecules and proteins (Pan et al., 2008; Xie et al., 2008; Zhang et al., 2008), we report here the crystal structure of the title compound.

The molecular structure of the title compound is illustrated in Fig. 1. In contrast to our previously reported structure of a related compound (Zhang et al., 2008), the conformation of the six-membered heterocyclic ring (N2/N3/C9—C12) in the title compound is close to a screw-boat, with atoms C11 and N3 out of the plane of the remaining four atoms by 0.681 (2) and 0.214 (2) Å, respectively. In the crystal structure, the dihedral angles of the phenyl rings (C1—C6) and (C15—C20) with the pyrazol ring (N1/N2/C7—C9) are 16.05 (10) and 84.84 (10)°, respectively. The crystal packing is stabilized by intermolecular C—H···O interactions and is further consolidated by C—H···π interactions (Table 1).

Related literature top

For the bioactivity of pyrazole derivatives, see: Farag et al. (2008); Pan et al. (2008); Szabó et al. (2008); Xie et al. (2008). For a related structure, see: Zhang et al. (2008). Cg1 and Cg2 are centroids of the C15–C20 and C1–C6 rings, respectively.

Experimental top

A solution containing ethyl-3-(4-chlorophenyl)-1-(2-bromoethyl)-1H-pyrazole-5-carboxylate (146 mg, 0.4 mmol), 2-(3,4-dimethoxyphenyl)ethanamine (724 mg, 4.0 mmol) and potassium iodide (13 mg, 0.08 mmol) in acetonitrile (10 ml) was refluxed under nitrogen for 3 h. Then the mixture was cooled, filtered, and the solvent was removed under reduced pressure. The product was obtained in 57% yield by column chromatography on silica gel using ethyl acetate as eluent. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid dissolved in ethyl acetate at room temperature for 5 days.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing displacement ellipsoids drawn at 30% probability level.

2-(4-Chlorophenyl)-5-(3,4-dimethoxyphenethyl)-6,7-dihydropyrazolo[1,5- a]pyrazin-4(5H)-one top

Crystal data top

C₂₂H₂₂ClN₃O₃	Z = 2
M_r = 411.88	F(000) = 432
Triclinic, P1	D_x = 1.386 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1709 (4) Å	Cell parameters from 2906 reflections
b = 10.6982 (5) Å	θ = 3.0–26.1°
c = 13.9169 (6) Å	µ = 0.22 mm⁻¹
α = 81.156 (3)°	T = 293 K
β = 77.150 (2)°	Block, colorless
γ = 72.278 (2)°	0.40 × 0.20 × 0.10 mm
V = 987.25 (8) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3999 independent reflections
Radiation source: fine-focus sealed tube	2969 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 26.4°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker 2005)	h = −7→8
T_min = 0.916, T_max = 0.978	k = −13→13
8654 measured reflections	l = −17→17

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0564P)² + 0.1941P] where P = (F_o² + 2F_c²)/3
3999 reflections	(Δ/σ)_max < 0.001
326 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₂H₂₂ClN₃O₃	γ = 72.278 (2)°
M_r = 411.88	V = 987.25 (8) Å³
Triclinic, P1	Z = 2
a = 7.1709 (4) Å	Mo Kα radiation
b = 10.6982 (5) Å	µ = 0.22 mm⁻¹
c = 13.9169 (6) Å	T = 293 K
α = 81.156 (3)°	0.40 × 0.20 × 0.10 mm
β = 77.150 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3999 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2005)	2969 reflections with I > 2σ(I)
T_min = 0.916, T_max = 0.978	R_int = 0.021
8654 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.20 e Å⁻³
3999 reflections	Δρ_min = −0.30 e Å⁻³
326 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
Cl	0.20421 (8)	0.95549 (6)	0.40014 (4)	0.06084 (19)
N1	−0.4397 (2)	0.70036 (14)	0.26041 (11)	0.0390 (4)
N2	−0.5553 (2)	0.69103 (14)	0.19947 (10)	0.0367 (4)
N3	−0.7921 (2)	0.70588 (15)	0.06451 (11)	0.0390 (4)
O1	−0.7274 (2)	0.89705 (14)	−0.00841 (10)	0.0575 (4)
O2	−1.3542 (2)	0.72159 (14)	−0.37111 (10)	0.0533 (4)
O3	−0.9862 (2)	0.58773 (15)	−0.41075 (10)	0.0544 (4)
C1	0.0314 (3)	0.91488 (18)	0.34943 (14)	0.0406 (4)
C2	−0.0785 (3)	0.8341 (2)	0.40461 (15)	0.0450 (5)
H2	−0.065 (3)	0.8025 (19)	0.4699 (15)	0.048 (6)*
C3	−0.2109 (3)	0.79940 (19)	0.36251 (14)	0.0419 (4)
H3	−0.289 (3)	0.744 (2)	0.3994 (15)	0.057 (6)*
C4	−0.2335 (3)	0.84383 (17)	0.26496 (12)	0.0343 (4)
C5	−0.1236 (3)	0.92790 (18)	0.21187 (14)	0.0390 (4)
H5	−0.135 (3)	0.9556 (19)	0.1468 (15)	0.046 (5)*
C6	0.0084 (3)	0.96339 (19)	0.25367 (14)	0.0411 (4)
H6	0.082 (3)	1.019 (2)	0.2150 (15)	0.049 (6)*
C7	−0.3707 (3)	0.80384 (17)	0.21908 (12)	0.0345 (4)
C8	−0.4449 (3)	0.86047 (19)	0.13250 (13)	0.0367 (4)
H8	−0.421 (3)	0.933 (2)	0.0897 (15)	0.047 (6)*
C9	−0.5643 (3)	0.78601 (17)	0.12271 (12)	0.0344 (4)
C10	−0.6987 (3)	0.80106 (19)	0.05288 (13)	0.0386 (4)
C11	−0.7288 (4)	0.5823 (2)	0.12678 (16)	0.0499 (5)
H11B	−0.842 (3)	0.543 (2)	0.1422 (16)	0.058 (6)*
H11A	−0.600 (4)	0.519 (2)	0.0875 (17)	0.066 (7)*
C12	−0.6833 (4)	0.6042 (2)	0.22192 (15)	0.0462 (5)
H12B	−0.611 (3)	0.522 (2)	0.2536 (15)	0.053 (6)*
H12A	−0.811 (4)	0.647 (2)	0.2650 (17)	0.069 (7)*
C13	−0.9414 (3)	0.7191 (2)	0.00409 (15)	0.0424 (5)
H13B	−1.051 (3)	0.684 (2)	0.0467 (15)	0.052 (6)*
C14	−0.8546 (3)	0.6485 (3)	−0.08922 (16)	0.0488 (5)
H14B	−0.807 (4)	0.551 (3)	−0.0693 (18)	0.073 (7)*
H14A	−0.736 (4)	0.676 (2)	−0.1225 (17)	0.066 (7)*
C15	−0.9982 (3)	0.67175 (18)	−0.16026 (13)	0.0383 (4)
C16	−1.1963 (3)	0.7426 (2)	−0.13969 (14)	0.0416 (4)
H16	−1.255 (3)	0.777 (2)	−0.0773 (16)	0.056 (6)*
C17	−1.3206 (3)	0.7617 (2)	−0.20844 (15)	0.0429 (5)
H17	−1.458 (3)	0.814 (2)	−0.1909 (14)	0.047 (6)*
C18	−1.2466 (3)	0.70993 (17)	−0.29847 (14)	0.0392 (4)
C19	−1.0451 (3)	0.63712 (18)	−0.32041 (13)	0.0387 (4)
C20	−0.9246 (3)	0.61940 (19)	−0.25182 (14)	0.0399 (4)
H20	−0.793 (4)	0.570 (2)	−0.2684 (15)	0.056 (6)*
C21	−1.5441 (3)	0.8157 (2)	−0.36227 (18)	0.0613 (6)
H21A	−1.6042	0.8145	−0.4172	0.092*
H21B	−1.5293	0.9018	−0.3621	0.092*
H21C	−1.6275	0.7944	−0.3016	0.092*
C22	−0.7782 (3)	0.5470 (2)	−0.45031 (16)	0.0593 (6)
H22A	−0.7578	0.5147	−0.5136	0.089*
H22B	−0.7124	0.4782	−0.4060	0.089*
H22C	−0.7243	0.6205	−0.4579	0.089*
H13A	−0.998 (3)	0.813 (2)	−0.0122 (14)	0.048 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0547 (4)	0.0822 (4)	0.0621 (4)	−0.0307 (3)	−0.0219 (3)	−0.0163 (3)
N1	0.0449 (9)	0.0398 (8)	0.0395 (8)	−0.0162 (7)	−0.0192 (7)	0.0006 (7)
N2	0.0410 (9)	0.0385 (8)	0.0365 (8)	−0.0167 (7)	−0.0151 (7)	0.0016 (6)
N3	0.0417 (9)	0.0462 (9)	0.0368 (8)	−0.0195 (7)	−0.0158 (7)	−0.0003 (7)
O1	0.0699 (10)	0.0651 (9)	0.0521 (8)	−0.0378 (8)	−0.0347 (8)	0.0235 (7)
O2	0.0527 (9)	0.0580 (9)	0.0527 (8)	−0.0050 (7)	−0.0288 (7)	−0.0097 (7)
O3	0.0521 (9)	0.0692 (10)	0.0418 (8)	−0.0064 (8)	−0.0151 (7)	−0.0174 (7)
C1	0.0382 (11)	0.0423 (10)	0.0462 (11)	−0.0098 (9)	−0.0149 (8)	−0.0116 (8)
C2	0.0546 (13)	0.0505 (11)	0.0368 (10)	−0.0187 (10)	−0.0192 (9)	−0.0009 (9)
C3	0.0489 (12)	0.0426 (11)	0.0398 (10)	−0.0193 (10)	−0.0133 (9)	0.0003 (8)
C4	0.0354 (10)	0.0353 (9)	0.0345 (9)	−0.0091 (8)	−0.0114 (8)	−0.0043 (7)
C5	0.0416 (11)	0.0415 (10)	0.0356 (10)	−0.0121 (9)	−0.0123 (8)	−0.0002 (8)
C6	0.0412 (11)	0.0422 (11)	0.0442 (11)	−0.0172 (9)	−0.0086 (9)	−0.0045 (8)
C7	0.0352 (10)	0.0355 (9)	0.0344 (9)	−0.0103 (8)	−0.0088 (8)	−0.0040 (7)
C8	0.0384 (10)	0.0402 (10)	0.0357 (9)	−0.0168 (9)	−0.0116 (8)	0.0021 (8)
C9	0.0353 (10)	0.0379 (9)	0.0319 (9)	−0.0126 (8)	−0.0093 (7)	0.0001 (7)
C10	0.0391 (11)	0.0468 (11)	0.0344 (10)	−0.0174 (9)	−0.0104 (8)	−0.0007 (8)
C11	0.0605 (15)	0.0477 (12)	0.0535 (12)	−0.0270 (12)	−0.0243 (11)	0.0039 (10)
C12	0.0566 (14)	0.0456 (12)	0.0471 (12)	−0.0281 (11)	−0.0209 (11)	0.0083 (10)
C13	0.0391 (11)	0.0545 (13)	0.0415 (11)	−0.0187 (10)	−0.0145 (9)	−0.0061 (9)
C14	0.0400 (12)	0.0676 (15)	0.0436 (11)	−0.0146 (11)	−0.0127 (9)	−0.0133 (10)
C15	0.0396 (11)	0.0434 (10)	0.0385 (10)	−0.0179 (9)	−0.0109 (8)	−0.0055 (8)
C16	0.0408 (11)	0.0498 (11)	0.0392 (10)	−0.0164 (9)	−0.0083 (9)	−0.0109 (9)
C17	0.0360 (11)	0.0456 (11)	0.0495 (11)	−0.0111 (9)	−0.0101 (9)	−0.0089 (9)
C18	0.0442 (11)	0.0368 (10)	0.0434 (10)	−0.0155 (9)	−0.0189 (9)	0.0003 (8)
C19	0.0448 (11)	0.0401 (10)	0.0346 (9)	−0.0140 (9)	−0.0116 (8)	−0.0029 (8)
C20	0.0374 (11)	0.0433 (11)	0.0407 (10)	−0.0108 (9)	−0.0102 (9)	−0.0060 (8)
C21	0.0494 (13)	0.0657 (15)	0.0729 (15)	−0.0083 (12)	−0.0315 (12)	−0.0051 (12)
C22	0.0617 (16)	0.0631 (14)	0.0478 (12)	−0.0061 (12)	−0.0090 (11)	−0.0142 (10)

Geometric parameters (Å, º) top

Cl—C1	1.7416 (18)	C9—C10	1.474 (2)
N1—N2	1.3439 (19)	C11—C12	1.499 (3)
N1—C7	1.346 (2)	C11—H11B	0.99 (2)
N2—C9	1.355 (2)	C11—H11A	1.06 (2)
N2—C12	1.452 (2)	C12—H12B	0.97 (2)
N3—C10	1.352 (2)	C12—H12A	1.00 (3)
N3—C13	1.465 (2)	C13—C14	1.516 (3)
N3—C11	1.470 (2)	C13—H13B	1.01 (2)
O1—C10	1.227 (2)	C13—H13A	0.97 (2)
O2—C18	1.372 (2)	C14—C15	1.523 (2)
O2—C21	1.418 (3)	C14—H14B	1.01 (3)
O3—C19	1.368 (2)	C14—H14A	0.98 (2)
O3—C22	1.425 (3)	C15—C16	1.380 (3)
C1—C2	1.378 (3)	C15—C20	1.399 (3)
C1—C6	1.380 (3)	C16—C17	1.401 (3)
C2—C3	1.383 (3)	C16—H16	0.95 (2)
C2—H2	0.94 (2)	C17—C18	1.377 (3)
C3—C4	1.396 (2)	C17—H17	0.97 (2)
C3—H3	0.95 (2)	C18—C19	1.407 (3)
C4—C5	1.394 (3)	C19—C20	1.380 (2)
C4—C7	1.476 (2)	C20—H20	0.93 (2)
C5—C6	1.382 (3)	C21—H21A	0.9600
C5—H5	0.92 (2)	C21—H21B	0.9600
C6—H6	0.95 (2)	C21—H21C	0.9600
C7—C8	1.402 (2)	C22—H22A	0.9600
C8—C9	1.374 (2)	C22—H22B	0.9600
C8—H8	0.94 (2)	C22—H22C	0.9600

N2—N1—C7	104.41 (13)	C11—C12—H12B	110.9 (12)
N1—N2—C9	112.51 (14)	N2—C12—H12A	109.6 (14)
N1—N2—C12	123.74 (14)	C11—C12—H12A	108.3 (13)
C9—N2—C12	122.94 (15)	H12B—C12—H12A	112.2 (19)
C10—N3—C13	119.09 (15)	N3—C13—C14	112.60 (17)
C10—N3—C11	121.19 (15)	N3—C13—H13B	107.6 (12)
C13—N3—C11	119.25 (15)	C14—C13—H13B	111.3 (12)
C18—O2—C21	117.38 (16)	N3—C13—H13A	107.0 (12)
C19—O3—C22	118.05 (15)	C14—C13—H13A	110.7 (12)
C2—C1—C6	120.98 (17)	H13B—C13—H13A	107.4 (17)
C2—C1—Cl	119.85 (14)	C13—C14—C15	114.67 (18)
C6—C1—Cl	119.16 (15)	C13—C14—H14B	108.3 (14)
C1—C2—C3	119.31 (18)	C15—C14—H14B	109.1 (14)
C1—C2—H2	121.1 (13)	C13—C14—H14A	108.0 (14)
C3—C2—H2	119.6 (13)	C15—C14—H14A	110.3 (13)
C2—C3—C4	121.06 (19)	H14B—C14—H14A	106 (2)
C2—C3—H3	120.8 (13)	C16—C15—C20	118.18 (17)
C4—C3—H3	118.2 (13)	C16—C15—C14	123.66 (17)
C5—C4—C3	118.22 (16)	C20—C15—C14	118.15 (17)
C5—C4—C7	120.68 (15)	C15—C16—C17	121.03 (18)
C3—C4—C7	121.10 (16)	C15—C16—H16	121.5 (13)
C6—C5—C4	120.96 (17)	C17—C16—H16	117.4 (13)
C6—C5—H5	120.4 (12)	C18—C17—C16	120.32 (19)
C4—C5—H5	118.6 (12)	C18—C17—H17	122.1 (12)
C1—C6—C5	119.42 (18)	C16—C17—H17	117.5 (12)
C1—C6—H6	121.9 (12)	O2—C18—C17	125.43 (18)
C5—C6—H6	118.7 (12)	O2—C18—C19	115.24 (16)
N1—C7—C8	111.40 (15)	C17—C18—C19	119.32 (17)
N1—C7—C4	120.36 (15)	O3—C19—C20	125.34 (18)
C8—C7—C4	128.23 (16)	O3—C19—C18	115.07 (15)
C9—C8—C7	104.71 (16)	C20—C19—C18	119.59 (17)
C9—C8—H8	126.3 (12)	C19—C20—C15	121.57 (19)
C7—C8—H8	129.0 (12)	C19—C20—H20	117.2 (13)
N2—C9—C8	106.96 (15)	C15—C20—H20	121.2 (13)
N2—C9—C10	120.98 (15)	O2—C21—H21A	109.5
C8—C9—C10	131.84 (16)	O2—C21—H21B	109.5
O1—C10—N3	123.38 (16)	H21A—C21—H21B	109.5
O1—C10—C9	121.11 (16)	O2—C21—H21C	109.5
N3—C10—C9	115.44 (15)	H21A—C21—H21C	109.5
N3—C11—C12	112.58 (17)	H21B—C21—H21C	109.5
N3—C11—H11B	106.1 (12)	O3—C22—H22A	109.5
C12—C11—H11B	108.8 (12)	O3—C22—H22B	109.5
N3—C11—H11A	109.6 (12)	H22A—C22—H22B	109.5
C12—C11—H11A	108.6 (12)	O3—C22—H22C	109.5
H11B—C11—H11A	111.2 (18)	H22A—C22—H22C	109.5
N2—C12—C11	108.36 (16)	H22B—C22—H22C	109.5
N2—C12—H12B	107.4 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.92 (2)	2.48 (2)	3.341 (2)	156.3 (17)
C8—H8···O1ⁱ	0.94 (2)	2.39 (2)	3.296 (2)	161.4 (19)
C11—H11B···Cg1ⁱⁱ	0.99 (2)	2.67 (2)	3.413 (2)	132.2 (16)
C12—H12A···Cg2ⁱⁱⁱ	1.00 (3)	2.77 (2)	3.640 (2)	146.2 (17)
C21—H21B···Cg2^iv	0.96	2.98	3.531 (2)	117

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₂ClN₃O₃
M_r	411.88
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.1709 (4), 10.6982 (5), 13.9169 (6)
α, β, γ (°)	81.156 (3), 77.150 (2), 72.278 (2)
V (Å³)	987.25 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 2005)
T_min, T_max	0.916, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	8654, 3999, 2969
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.115, 1.03
No. of reflections	3999
No. of parameters	326
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.30

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.92 (2)	2.48 (2)	3.341 (2)	156.3 (17)
C8—H8···O1ⁱ	0.94 (2)	2.39 (2)	3.296 (2)	161.4 (19)
C11—H11B···Cg1ⁱⁱ	0.99 (2)	2.67 (2)	3.413 (2)	132.2 (16)
C12—H12A···Cg2ⁱⁱⁱ	1.00 (3)	2.77 (2)	3.640 (2)	146.2 (17)
C21—H21B···Cg2^iv	0.96	2.98	3.531 (2)	117

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

Acknowledgements

This study was supported by the Science and Technology Developmental Project of Shandong Province (2008 GG10002034).

References

Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farag, A. M., Mayhoub, A. S., Barakatb, S. E. & Bayomi, A. H. (2008). Bioorg. Med. Chem. 16, 4569–4578. Web of Science CrossRef PubMed CAS Google Scholar
Pan, X. H., Liu, X., Zhao, B. X., Xie, Y. S., Shin, D. S., Zhang, S. L., Zhao, J. & Miao, J. Y. (2008). Bioorg. Med. Chem. 16, 9093–9100. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Szabó, G.; Fischer, J.; Kis-Varga, Á. & Gyires, K. (2008). J. Med. Chem. 51, 142–147. Web of Science PubMed Google Scholar
Xie, Y. S., Pan, X. H., Zhao, B. X., Liu, J. T., Shin, D. S., Zhang, J. H., Zheng, L. W., Zhao, J. & Miao, J. Y. (2008). J. Organomet. Chem. 693, 1367–1374. Web of Science CSD CrossRef CAS Google Scholar
Zhang, J. H., Fan, C. D., Zhao, B. X., Shin, D. S., Dong, W. L., Xie, Y. S. & Miao, J. Y. (2008). Bioorg. Med. Chem. 16, 10165–10171. Web of Science CSD CrossRef PubMed CAS Google Scholar

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Volume 65| Part 7| July 2009| Page o1457

doi:10.1107/S1600536809020212

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

2-(4-Chloro­phen­yl)-5-(3,4-di­meth­oxy­pheneth­yl)-6,7-di­hydro­pyrazolo[1,5-a]pyrazin-4(5H)-one

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Experimental

Crystal data

Data collection

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References

organic compounds

2-(4-Chlorophenyl)-5-(3,4-dimethoxyphenethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one