2-(4-Chloro-phen-yl)-5-(3,4-dimethoxy-pheneth-yl)-6,7-dihydro-pyrazolo[1,5-a]pyrazin-4(5H)-one.

In the title compound, C(22)H(22)ClN(3)O(3), 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 inter-molecular C-H⋯O inter-actions and is also consolidated by C-H⋯π inter-actions.

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 = 411.88

Triclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 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

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.

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

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

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

C22H22ClN3O3	Z = 2
Mr = 411.88	F(000) = 432
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0564P)2 + 0.1941P] where P = (Fo2 + 2Fc2)/3
3999 reflections	(Δ/σ)max < 0.001
326 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.30 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
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)*

	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)

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)

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···Cg2iv	0.96	2.98	3.531 (2)	117

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) ; (ii) ; (iii) . Cg1 and Cg2 are centroids of the C15–C20 and C1–C6 rings, respectively.