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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 7| July 2009| Page o1457
doi:10.1107/S1600536809020212

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 Xiea and Bao-Xiang Zhaoa*

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[Farag, A. M., Mayhoub, A. S., Barakatb, S. E. & Bayomi, A. H. (2008). Bioorg. Med. Chem. 16, 4569-4578.]); Pan et al. (2008[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.]); Szabó et al. (2008[Szabó, G.; Fischer, J.; Kis-Varga, Á. & Gyires, K. (2008). J. Med. Chem. 51, 142-147.]); Xie et al. (2008[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.]). For a related structure, see: Zhang et al. (2008[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.]).

[Scheme 1]

Experimental

Crystal data

  • C22H22ClN3O3

  • Mr = 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[Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.916, Tmax = 0.978

  • 8654 measured reflections

  • 3999 independent reflections

  • 2969 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.20 e Å−3

  • Δρmin = −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[Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.

Refinement top

The H atoms were located in difference Fourier maps, their positional and isotropic vibrational parameters were refined freely except for the methyl H-atoms which were included in the refinements at geometrically idealized positions in riding mode with C–H = 0.96 Å and Uiso(H) = 1.5 Ueq(C).

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
[Figure 1] 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
C22H22ClN3O3Z = 2
Mr = 411.88F(000) = 432
Triclinic, P1Dx = 1.386 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1709 (4) ÅCell parameters from 2906 reflections
b = 10.6982 (5) Åθ = 3.0–26.1°
c = 13.9169 (6) ŵ = 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 tube2969 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ϕ and ω scansθmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker 2005)		h = −7→8
Tmin = 0.916, Tmax = 0.978k = −13→13
8654 measured reflectionsl = −17→17
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0564P)2 + 0.1941P]
where P = (Fo2 + 2Fc2)/3
3999 reflections(Δ/σ)max < 0.001
326 parametersΔρmax = 0.20 e Å−3
0 restraintsΔρmin = −0.30 e Å−3
Crystal data top
C22H22ClN3O3γ = 72.278 (2)°
Mr = 411.88V = 987.25 (8) Å3
Triclinic, P1Z = 2
a = 7.1709 (4) ÅMo Kα radiation
b = 10.6982 (5) ŵ = 0.22 mm−1
c = 13.9169 (6) ÅT = 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)
Tmin = 0.916, Tmax = 0.978Rint = 0.021
8654 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.20 e Å−3
3999 reflectionsΔρmin = −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
xyzUiso*/Ueq
Cl0.20421 (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)
C10.0314 (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)*
C60.0084 (3)0.96339 (19)0.25367 (14)0.0411 (4)
H60.082 (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−1.60420.8145−0.41720.092*
H21B−1.52930.9018−0.36210.092*
H21C−1.62750.7944−0.30160.092*
C22−0.7782 (3)0.5470 (2)−0.45031 (16)0.0593 (6)
H22A−0.75780.5147−0.51360.089*
H22B−0.71240.4782−0.40600.089*
H22C−0.72430.6205−0.45790.089*
H13A−0.998 (3)0.813 (2)−0.0122 (14)0.048 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0547 (4)0.0822 (4)0.0621 (4)−0.0307 (3)−0.0219 (3)−0.0163 (3)
N10.0449 (9)0.0398 (8)0.0395 (8)−0.0162 (7)−0.0192 (7)0.0006 (7)
N20.0410 (9)0.0385 (8)0.0365 (8)−0.0167 (7)−0.0151 (7)0.0016 (6)
N30.0417 (9)0.0462 (9)0.0368 (8)−0.0195 (7)−0.0158 (7)−0.0003 (7)
O10.0699 (10)0.0651 (9)0.0521 (8)−0.0378 (8)−0.0347 (8)0.0235 (7)
O20.0527 (9)0.0580 (9)0.0527 (8)−0.0050 (7)−0.0288 (7)−0.0097 (7)
O30.0521 (9)0.0692 (10)0.0418 (8)−0.0064 (8)−0.0151 (7)−0.0174 (7)
C10.0382 (11)0.0423 (10)0.0462 (11)−0.0098 (9)−0.0149 (8)−0.0116 (8)
C20.0546 (13)0.0505 (11)0.0368 (10)−0.0187 (10)−0.0192 (9)−0.0009 (9)
C30.0489 (12)0.0426 (11)0.0398 (10)−0.0193 (10)−0.0133 (9)0.0003 (8)
C40.0354 (10)0.0353 (9)0.0345 (9)−0.0091 (8)−0.0114 (8)−0.0043 (7)
C50.0416 (11)0.0415 (10)0.0356 (10)−0.0121 (9)−0.0123 (8)−0.0002 (8)
C60.0412 (11)0.0422 (11)0.0442 (11)−0.0172 (9)−0.0086 (9)−0.0045 (8)
C70.0352 (10)0.0355 (9)0.0344 (9)−0.0103 (8)−0.0088 (8)−0.0040 (7)
C80.0384 (10)0.0402 (10)0.0357 (9)−0.0168 (9)−0.0116 (8)0.0021 (8)
C90.0353 (10)0.0379 (9)0.0319 (9)−0.0126 (8)−0.0093 (7)0.0001 (7)
C100.0391 (11)0.0468 (11)0.0344 (10)−0.0174 (9)−0.0104 (8)−0.0007 (8)
C110.0605 (15)0.0477 (12)0.0535 (12)−0.0270 (12)−0.0243 (11)0.0039 (10)
C120.0566 (14)0.0456 (12)0.0471 (12)−0.0281 (11)−0.0209 (11)0.0083 (10)
C130.0391 (11)0.0545 (13)0.0415 (11)−0.0187 (10)−0.0145 (9)−0.0061 (9)
C140.0400 (12)0.0676 (15)0.0436 (11)−0.0146 (11)−0.0127 (9)−0.0133 (10)
C150.0396 (11)0.0434 (10)0.0385 (10)−0.0179 (9)−0.0109 (8)−0.0055 (8)
C160.0408 (11)0.0498 (11)0.0392 (10)−0.0164 (9)−0.0083 (9)−0.0109 (9)
C170.0360 (11)0.0456 (11)0.0495 (11)−0.0111 (9)−0.0101 (9)−0.0089 (9)
C180.0442 (11)0.0368 (10)0.0434 (10)−0.0155 (9)−0.0189 (9)0.0003 (8)
C190.0448 (11)0.0401 (10)0.0346 (9)−0.0140 (9)−0.0116 (8)−0.0029 (8)
C200.0374 (11)0.0433 (11)0.0407 (10)−0.0108 (9)−0.0102 (9)−0.0060 (8)
C210.0494 (13)0.0657 (15)0.0729 (15)−0.0083 (12)−0.0315 (12)−0.0051 (12)
C220.0617 (16)0.0631 (14)0.0478 (12)−0.0061 (12)−0.0090 (11)−0.0142 (10)
Geometric parameters (Å, º) top
Cl—C11.7416 (18)C9—C101.474 (2)
N1—N21.3439 (19)C11—C121.499 (3)
N1—C71.346 (2)C11—H11B0.99 (2)
N2—C91.355 (2)C11—H11A1.06 (2)
N2—C121.452 (2)C12—H12B0.97 (2)
N3—C101.352 (2)C12—H12A1.00 (3)
N3—C131.465 (2)C13—C141.516 (3)
N3—C111.470 (2)C13—H13B1.01 (2)
O1—C101.227 (2)C13—H13A0.97 (2)
O2—C181.372 (2)C14—C151.523 (2)
O2—C211.418 (3)C14—H14B1.01 (3)
O3—C191.368 (2)C14—H14A0.98 (2)
O3—C221.425 (3)C15—C161.380 (3)
C1—C21.378 (3)C15—C201.399 (3)
C1—C61.380 (3)C16—C171.401 (3)
C2—C31.383 (3)C16—H160.95 (2)
C2—H20.94 (2)C17—C181.377 (3)
C3—C41.396 (2)C17—H170.97 (2)
C3—H30.95 (2)C18—C191.407 (3)
C4—C51.394 (3)C19—C201.380 (2)
C4—C71.476 (2)C20—H200.93 (2)
C5—C61.382 (3)C21—H21A0.9600
C5—H50.92 (2)C21—H21B0.9600
C6—H60.95 (2)C21—H21C0.9600
C7—C81.402 (2)C22—H22A0.9600
C8—C91.374 (2)C22—H22B0.9600
C8—H80.94 (2)C22—H22C0.9600
N2—N1—C7104.41 (13)C11—C12—H12B110.9 (12)
N1—N2—C9112.51 (14)N2—C12—H12A109.6 (14)
N1—N2—C12123.74 (14)C11—C12—H12A108.3 (13)
C9—N2—C12122.94 (15)H12B—C12—H12A112.2 (19)
C10—N3—C13119.09 (15)N3—C13—C14112.60 (17)
C10—N3—C11121.19 (15)N3—C13—H13B107.6 (12)
C13—N3—C11119.25 (15)C14—C13—H13B111.3 (12)
C18—O2—C21117.38 (16)N3—C13—H13A107.0 (12)
C19—O3—C22118.05 (15)C14—C13—H13A110.7 (12)
C2—C1—C6120.98 (17)H13B—C13—H13A107.4 (17)
C2—C1—Cl119.85 (14)C13—C14—C15114.67 (18)
C6—C1—Cl119.16 (15)C13—C14—H14B108.3 (14)
C1—C2—C3119.31 (18)C15—C14—H14B109.1 (14)
C1—C2—H2121.1 (13)C13—C14—H14A108.0 (14)
C3—C2—H2119.6 (13)C15—C14—H14A110.3 (13)
C2—C3—C4121.06 (19)H14B—C14—H14A106 (2)
C2—C3—H3120.8 (13)C16—C15—C20118.18 (17)
C4—C3—H3118.2 (13)C16—C15—C14123.66 (17)
C5—C4—C3118.22 (16)C20—C15—C14118.15 (17)
C5—C4—C7120.68 (15)C15—C16—C17121.03 (18)
C3—C4—C7121.10 (16)C15—C16—H16121.5 (13)
C6—C5—C4120.96 (17)C17—C16—H16117.4 (13)
C6—C5—H5120.4 (12)C18—C17—C16120.32 (19)
C4—C5—H5118.6 (12)C18—C17—H17122.1 (12)
C1—C6—C5119.42 (18)C16—C17—H17117.5 (12)
C1—C6—H6121.9 (12)O2—C18—C17125.43 (18)
C5—C6—H6118.7 (12)O2—C18—C19115.24 (16)
N1—C7—C8111.40 (15)C17—C18—C19119.32 (17)
N1—C7—C4120.36 (15)O3—C19—C20125.34 (18)
C8—C7—C4128.23 (16)O3—C19—C18115.07 (15)
C9—C8—C7104.71 (16)C20—C19—C18119.59 (17)
C9—C8—H8126.3 (12)C19—C20—C15121.57 (19)
C7—C8—H8129.0 (12)C19—C20—H20117.2 (13)
N2—C9—C8106.96 (15)C15—C20—H20121.2 (13)
N2—C9—C10120.98 (15)O2—C21—H21A109.5
C8—C9—C10131.84 (16)O2—C21—H21B109.5
O1—C10—N3123.38 (16)H21A—C21—H21B109.5
O1—C10—C9121.11 (16)O2—C21—H21C109.5
N3—C10—C9115.44 (15)H21A—C21—H21C109.5
N3—C11—C12112.58 (17)H21B—C21—H21C109.5
N3—C11—H11B106.1 (12)O3—C22—H22A109.5
C12—C11—H11B108.8 (12)O3—C22—H22B109.5
N3—C11—H11A109.6 (12)H22A—C22—H22B109.5
C12—C11—H11A108.6 (12)O3—C22—H22C109.5
H11B—C11—H11A111.2 (18)H22A—C22—H22C109.5
N2—C12—C11108.36 (16)H22B—C22—H22C109.5
N2—C12—H12B107.4 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.92 (2)2.48 (2)3.341 (2)156.3 (17)
C8—H8···O1i0.94 (2)2.39 (2)3.296 (2)161.4 (19)
C11—H11B···Cg1ii0.99 (2)2.67 (2)3.413 (2)132.2 (16)
C12—H12A···Cg2iii1.00 (3)2.77 (2)3.640 (2)146.2 (17)
C21—H21B···Cg2iv0.962.983.531 (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 formulaC22H22ClN3O3
Mr411.88
Crystal system, space groupTriclinic, 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)
Z2
Radiation typeMo Kα
µ (mm−1)0.22
Crystal size (mm)0.40 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker 2005)
Tmin, Tmax0.916, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections		8654, 3999, 2969
Rint0.021
(sin θ/λ)max (Å−1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.115, 1.03
No. of reflections3999
No. of parameters326
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (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···AD—HH···AD···AD—H···A
C5—H5···O1i0.92 (2)2.48 (2)3.341 (2)156.3 (17)
C8—H8···O1i0.94 (2)2.39 (2)3.296 (2)161.4 (19)
C11—H11B···Cg1ii0.99 (2)2.67 (2)3.413 (2)132.2 (16)
C12—H12A···Cg2iii1.00 (3)2.77 (2)3.640 (2)146.2 (17)
C21—H21B···Cg2iv0.962.983.531 (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

First citationBruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarag, 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
 First citationPan, 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
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSzabó, G.; Fischer, J.; Kis-Varga, Á. & Gyires, K. (2008). J. Med. Chem. 51, 142–147.  Web of Science PubMed Google Scholar
 First citationXie, 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
 First citationZhang, 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 65| Part 7| July 2009| Page o1457
doi:10.1107/S1600536809020212
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