7-Chloro-5-(2-ethoxy­phen­yl)-1-methyl-3-propyl-2,6-dihydro-1H-pyrazolo[4,3-d]pyrimidine

Zhou, M.-Q.; Zhu, K.; Lv, X.-P.; Han, P.-F.; Wei, P.

doi:10.1107/S1600536809033911

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2318

doi:10.1107/S1600536809033911

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7-Chloro-5-(2-ethoxyphenyl)-1-methyl-3-propyl-2,6-dihydro-1H-pyrazolo[4,3-d]pyrimidine

Ming-Qiu Zhou,^a Kai Zhu,^a Xiao-Ping Lv,^a Ping-Fang Han ^a ^* and Ping Wei ^a

^aCollege of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technolgy, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: hpf@njut.edu.cn

(Received 21 August 2009; accepted 25 August 2009; online 5 September 2009)

In the title compound, C₁₇H₂₁ClN₄O, the benzene ring is oriented at dihedral angles of 1.59 (3) and 1.27 (3)° with respect to the pyrimidine and pyrazole rings, while the dihedral angle between the pyrimidine and pyrazole rings is 0.83 (3)°. An intramolecular N—H⋯O hydrogen bond results in the formation of a planar (r.m.s. deviation 0.004 Å) six-membered ring.

Related literature

For a related structure, see: Rajesh & Joshi (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₂₁ClN₄O
M_r = 332.83
Triclinic, $[P \overline 1]$
a = 4.6700 (9) Å
b = 11.647 (2) Å
c = 16.064 (3) Å
α = 78.56 (3)°
β = 86.75 (3)°
γ = 79.81 (3)°
V = 842.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 294 K
0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.932, T_max = 0.977
3470 measured reflections
3061 independent reflections
2353 reflections with I > 2σ(I)
R_int = 0.033
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.182
S = 1.00
3061 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	1.91	2.616 (3)	138

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033911/hk2761sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033911/hk2761Isup2.hkl

checkCIF report

Comment top

Some derivatives of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7H -pyrazolo[4,3-d]pyrimidin-7-one are important chemical materials. We report herein the crystal structure of the title compound.

In the molecule of the title compound, (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C3-C8), B (N1/N2/C9-C12) and C (N3/N4/C10/C11/C13) are, of course, planar. The dihedral angles between them are A/B = 1.59 (3), A/C = 1.27 (3) and B/C = 0.83 (3) °. The intramolecular N-H···O hydrogen bond (Table 1) results in the formation of a planar six-membered ring D (O1/N1/C3/C8/C9/H1A), which is oriented with respect to the other rings at dihedral angles of A/D = 1.01 (3), B/D = 0.63 (3) and C/D = 0.83 (3) °. So, the rings are almost coplanar.

Related literature top

For a related structure, see: Rajesh & Joshi (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, 5-(2-ethoxyphenyl)-1-methyl-3-propyl -1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (15.6 g) and phosphorus trichloride (13.7 g) were added into carbon tetrachloride (100 ml) at 345-350 K. The gross products were extracted with n-hexane, dried under vaccum, and then recrystallized in dichloromethane. Finally the title compound is obtained (yield; 1.5 g) (Rajesh et al., 2007). Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Hydrogen bond is shown as dashed line.

7-Chloro-5-(2-ethoxyphenyl)-1-methyl-3-propyl-2,6-dihydro- 1H-pyrazolo[4,3-d]pyrimidine top

Crystal data top

C₁₇H₂₁ClN₄O	Z = 2
M_r = 332.83	F(000) = 352
Triclinic, P1	D_x = 1.312 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.6700 (9) Å	Cell parameters from 25 reflections
b = 11.647 (2) Å	θ = 9–13°
c = 16.064 (3) Å	µ = 0.24 mm⁻¹
α = 78.56 (3)°	T = 294 K
β = 86.75 (3)°	BlocK, yellow
γ = 79.81 (3)°	0.30 × 0.10 × 0.10 mm
V = 842.7 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	2353 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 25.3°, θ_min = 1.3°
ω/2θ scans	h = 0→5
Absorption correction: ψ scan (North et al., 1968)	k = −13→13
T_min = 0.932, T_max = 0.977	l = −19→19
3470 measured reflections	3 standard reflections every 120 min
3061 independent reflections	intensity decay: 1%

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1P)² + 0.6P] where P = (F_o² + 2F_c²)/3
3061 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₁₇H₂₁ClN₄O	γ = 79.81 (3)°
M_r = 332.83	V = 842.7 (3) Å³
Triclinic, P1	Z = 2
a = 4.6700 (9) Å	Mo Kα radiation
b = 11.647 (2) Å	µ = 0.24 mm⁻¹
c = 16.064 (3) Å	T = 294 K
α = 78.56 (3)°	0.30 × 0.10 × 0.10 mm
β = 86.75 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2353 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.033
T_min = 0.932, T_max = 0.977	3 standard reflections every 120 min
3470 measured reflections	intensity decay: 1%
3061 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.182	H-atom parameters constrained
S = 1.00	Δρ_max = 0.38 e Å⁻³
3061 reflections	Δρ_min = −0.52 e Å⁻³
208 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	0.45734 (19)	0.18716 (7)	0.56202 (5)	0.0581 (3)
O1	0.4864 (5)	0.49028 (18)	0.68108 (14)	0.0528 (6)
N1	0.6871 (5)	0.2658 (2)	0.68131 (14)	0.0420 (6)
H1A	0.5753	0.3313	0.6613	0.050*
N2	1.0314 (5)	0.1732 (2)	0.78486 (14)	0.0414 (6)
N3	1.1345 (6)	−0.1091 (2)	0.72458 (16)	0.0506 (7)
H3A	1.2075	−0.1828	0.7269	0.061*
N4	0.9354 (6)	−0.0435 (2)	0.66884 (16)	0.0466 (6)
C1	0.1508 (7)	0.5709 (3)	0.5722 (2)	0.0605 (9)
H1B	0.0284	0.6416	0.5443	0.091*
H1C	0.0335	0.5119	0.5956	0.091*
H1D	0.2893	0.5410	0.5319	0.091*
C2	0.3079 (7)	0.5992 (3)	0.6417 (2)	0.0550 (8)
H2B	0.4278	0.6587	0.6189	0.066*
H2C	0.1703	0.6297	0.6829	0.066*
C3	0.6554 (7)	0.4882 (3)	0.74759 (19)	0.0452 (7)
C4	0.6545 (8)	0.5877 (3)	0.7839 (2)	0.0597 (9)
H4A	0.5325	0.6587	0.7632	0.072*
C5	0.8344 (9)	0.5806 (3)	0.8503 (2)	0.0671 (10)
H5A	0.8325	0.6470	0.8744	0.081*
C6	1.0161 (9)	0.4770 (3)	0.8812 (2)	0.0635 (9)
H6A	1.1384	0.4735	0.9257	0.076*
C7	1.0177 (7)	0.3782 (3)	0.8465 (2)	0.0528 (8)
H7A	1.1418	0.3082	0.8683	0.063*
C8	0.8384 (6)	0.3800 (3)	0.77958 (18)	0.0428 (7)
C9	0.8566 (6)	0.2674 (2)	0.74811 (17)	0.0393 (6)
C10	1.0325 (6)	0.0743 (2)	0.75138 (17)	0.0397 (6)
C11	0.8671 (6)	0.0690 (2)	0.68347 (17)	0.0398 (6)
C12	0.6759 (6)	0.1717 (2)	0.64296 (17)	0.0389 (6)
C13	1.1973 (6)	−0.0409 (3)	0.77464 (19)	0.0443 (7)
C14	0.8296 (8)	−0.0978 (3)	0.6049 (2)	0.0606 (9)
H14A	0.9214	−0.1795	0.6116	0.091*
H14B	0.8752	−0.0562	0.5493	0.091*
H14C	0.6226	−0.0934	0.6116	0.091*
C15	1.3994 (7)	−0.0863 (3)	0.84708 (19)	0.0502 (8)
H15A	1.4993	−0.0232	0.8551	0.060*
H15B	1.5449	−0.1506	0.8332	0.060*
C16	1.2456 (9)	−0.1304 (5)	0.9283 (2)	0.0868 (14)
H16A	1.0974	−0.0661	0.9409	0.104*
H16B	1.1471	−0.1936	0.9197	0.104*
C17	1.4345 (10)	−0.1757 (5)	1.0040 (2)	0.0865 (13)
H17A	1.3173	−0.2021	1.0527	0.130*
H17B	1.5283	−0.1132	1.0147	0.130*
H17C	1.5793	−0.2410	0.9932	0.130*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0624 (5)	0.0586 (5)	0.0533 (5)	−0.0064 (4)	−0.0254 (4)	−0.0076 (4)
O1	0.0595 (13)	0.0387 (11)	0.0578 (13)	0.0041 (10)	−0.0213 (11)	−0.0087 (9)
N1	0.0438 (13)	0.0384 (13)	0.0421 (13)	−0.0020 (10)	−0.0136 (11)	−0.0050 (10)
N2	0.0417 (13)	0.0432 (13)	0.0385 (12)	−0.0065 (10)	−0.0090 (10)	−0.0040 (10)
N3	0.0554 (16)	0.0390 (13)	0.0539 (15)	0.0040 (12)	−0.0135 (12)	−0.0079 (11)
N4	0.0530 (15)	0.0395 (13)	0.0472 (14)	−0.0013 (11)	−0.0119 (12)	−0.0106 (11)
C1	0.0518 (19)	0.061 (2)	0.063 (2)	0.0071 (16)	−0.0128 (16)	−0.0078 (17)
C2	0.0521 (19)	0.0433 (17)	0.063 (2)	0.0070 (14)	−0.0095 (16)	−0.0055 (15)
C3	0.0453 (16)	0.0440 (16)	0.0469 (17)	−0.0074 (13)	−0.0020 (13)	−0.0102 (13)
C4	0.065 (2)	0.0452 (18)	0.070 (2)	−0.0044 (16)	−0.0089 (18)	−0.0163 (16)
C5	0.081 (3)	0.057 (2)	0.072 (2)	−0.0113 (19)	−0.012 (2)	−0.0298 (18)
C6	0.074 (2)	0.065 (2)	0.057 (2)	−0.0163 (19)	−0.0199 (18)	−0.0194 (17)
C7	0.0583 (19)	0.0499 (18)	0.0516 (18)	−0.0076 (15)	−0.0168 (15)	−0.0102 (14)
C8	0.0430 (16)	0.0428 (16)	0.0432 (15)	−0.0088 (13)	−0.0052 (13)	−0.0068 (12)
C9	0.0376 (14)	0.0407 (15)	0.0383 (14)	−0.0069 (12)	−0.0037 (12)	−0.0037 (12)
C10	0.0399 (15)	0.0404 (15)	0.0374 (14)	−0.0049 (12)	−0.0043 (12)	−0.0044 (12)
C11	0.0409 (15)	0.0400 (15)	0.0379 (14)	−0.0066 (12)	−0.0045 (12)	−0.0048 (12)
C12	0.0376 (14)	0.0413 (15)	0.0377 (14)	−0.0097 (12)	−0.0031 (12)	−0.0040 (12)
C13	0.0419 (16)	0.0431 (16)	0.0441 (16)	−0.0004 (12)	−0.0055 (13)	−0.0042 (13)
C14	0.074 (2)	0.0503 (19)	0.061 (2)	−0.0034 (17)	−0.0181 (18)	−0.0203 (16)
C15	0.0476 (17)	0.0463 (17)	0.0524 (18)	0.0036 (13)	−0.0128 (14)	−0.0060 (14)
C16	0.060 (2)	0.135 (4)	0.057 (2)	−0.028 (2)	−0.0162 (19)	0.014 (2)
C17	0.081 (3)	0.117 (4)	0.055 (2)	−0.024 (3)	−0.015 (2)	0.010 (2)

Geometric parameters (Å, º) top

Cl—C12	1.660 (3)	C5—C6	1.367 (5)
O1—C2	1.439 (4)	C5—H5A	0.9300
O1—C3	1.358 (4)	C6—C7	1.373 (5)
N1—C9	1.374 (3)	C6—H6A	0.9300
N1—C12	1.369 (4)	C7—C8	1.395 (4)
N1—H1A	0.8600	C7—H7A	0.9300
N2—C9	1.304 (4)	C8—C9	1.484 (4)
N2—C10	1.363 (4)	C10—C11	1.389 (4)
N3—N4	1.350 (3)	C10—C13	1.414 (4)
N3—C13	1.315 (4)	C11—C12	1.425 (4)
N3—H3A	0.8600	C13—C15	1.493 (4)
N4—C11	1.356 (4)	C14—H14A	0.9600
N4—C14	1.458 (4)	C14—H14B	0.9600
C1—C2	1.489 (5)	C14—H14C	0.9600
C1—H1B	0.9600	C15—C16	1.497 (5)
C1—H1C	0.9600	C15—H15A	0.9700
C1—H1D	0.9600	C15—H15B	0.9700
C2—H2B	0.9700	C16—C17	1.496 (5)
C2—H2C	0.9700	C16—H16A	0.9700
C3—C4	1.396 (4)	C16—H16B	0.9700
C3—C8	1.412 (4)	C17—H17A	0.9600
C4—C5	1.375 (5)	C17—H17B	0.9600
C4—H4A	0.9300	C17—H17C	0.9600

C3—O1—C2	120.4 (2)	C3—C8—C9	125.6 (3)
C12—N1—C9	127.4 (2)	N2—C9—N1	122.1 (3)
C12—N1—H1A	116.3	N2—C9—C8	119.1 (3)
C9—N1—H1A	116.3	N1—C9—C8	118.8 (2)
C9—N2—C10	114.6 (2)	N2—C10—C11	125.1 (3)
C13—N3—N4	108.1 (2)	N2—C10—C13	129.4 (3)
C13—N3—H3A	125.9	C11—C10—C13	105.4 (3)
N4—N3—H3A	125.9	N4—C11—C10	106.8 (2)
N3—N4—C11	110.3 (2)	N4—C11—C12	132.7 (3)
N3—N4—C14	119.5 (2)	C10—C11—C12	120.5 (3)
C11—N4—C14	130.2 (3)	N1—C12—C11	110.1 (2)
C2—C1—H1B	109.5	N1—C12—Cl	120.5 (2)
C2—C1—H1C	109.5	C11—C12—Cl	129.4 (2)
H1B—C1—H1C	109.5	N3—C13—C10	109.3 (3)
C2—C1—H1D	109.5	N3—C13—C15	122.6 (3)
H1B—C1—H1D	109.5	C10—C13—C15	127.9 (3)
H1C—C1—H1D	109.5	N4—C14—H14A	109.5
O1—C2—C1	106.9 (3)	N4—C14—H14B	109.5
O1—C2—H2B	110.3	H14A—C14—H14B	109.5
C1—C2—H2B	110.3	N4—C14—H14C	109.5
O1—C2—H2C	110.3	H14A—C14—H14C	109.5
C1—C2—H2C	110.3	H14B—C14—H14C	109.5
H2B—C2—H2C	108.6	C13—C15—C16	112.7 (3)
O1—C3—C4	122.6 (3)	C13—C15—H15A	109.1
O1—C3—C8	117.3 (3)	C16—C15—H15A	109.1
C4—C3—C8	120.1 (3)	C13—C15—H15B	109.1
C5—C4—C3	119.9 (3)	C16—C15—H15B	109.1
C5—C4—H4A	120.0	H15A—C15—H15B	107.8
C3—C4—H4A	120.0	C17—C16—C15	115.6 (3)
C6—C5—C4	120.8 (3)	C17—C16—H16A	108.4
C6—C5—H5A	119.6	C15—C16—H16A	108.4
C4—C5—H5A	119.6	C17—C16—H16B	108.4
C5—C6—C7	119.9 (3)	C15—C16—H16B	108.4
C5—C6—H6A	120.1	H16A—C16—H16B	107.5
C7—C6—H6A	120.1	C16—C17—H17A	109.5
C6—C7—C8	121.8 (3)	C16—C17—H17B	109.5
C6—C7—H7A	119.1	H17A—C17—H17B	109.5
C8—C7—H7A	119.1	C16—C17—H17C	109.5
C7—C8—C3	117.5 (3)	H17A—C17—H17C	109.5
C7—C8—C9	116.9 (3)	H17B—C17—H17C	109.5

C3—O1—C2—C1	−179.6 (3)	C6—C7—C8—C9	−179.3 (3)
C2—O1—C3—C4	3.4 (5)	O1—C3—C8—C7	178.4 (3)
C2—O1—C3—C8	−176.2 (3)	C4—C3—C8—C7	−1.2 (5)
C12—N1—C9—N2	−1.2 (5)	O1—C3—C8—C9	−1.6 (5)
C12—N1—C9—C8	179.2 (3)	C4—C3—C8—C9	178.8 (3)
C9—N1—C12—C11	1.1 (4)	C7—C8—C9—N2	1.4 (4)
C9—N1—C12—Cl	−179.6 (2)	C3—C8—C9—N2	−178.6 (3)
C10—N2—C9—N1	0.4 (4)	C7—C8—C9—N1	−179.0 (3)
C10—N2—C9—C8	180.0 (2)	C3—C8—C9—N1	1.1 (4)
C9—N2—C10—C11	0.3 (4)	N2—C10—C11—N4	178.7 (3)
C9—N2—C10—C13	178.9 (3)	C13—C10—C11—N4	−0.2 (3)
C13—N3—N4—C11	−0.4 (3)	N2—C10—C11—C12	−0.3 (4)
C13—N3—N4—C14	179.3 (3)	C13—C10—C11—C12	−179.1 (3)
N4—N3—C13—C10	0.2 (3)	N4—C11—C12—N1	−179.1 (3)
N4—N3—C13—C15	176.7 (3)	C10—C11—C12—N1	−0.4 (4)
N3—N4—C11—C10	0.3 (3)	N4—C11—C12—Cl	1.7 (5)
C14—N4—C11—C10	−179.3 (3)	C10—C11—C12—Cl	−179.6 (2)
N3—N4—C11—C12	179.1 (3)	N2—C10—C13—N3	−178.9 (3)
C14—N4—C11—C12	−0.5 (6)	C11—C10—C13—N3	−0.1 (3)
O1—C3—C4—C5	−178.9 (3)	N2—C10—C13—C15	4.9 (5)
C8—C3—C4—C5	0.7 (5)	C11—C10—C13—C15	−176.3 (3)
C3—C4—C5—C6	0.3 (6)	N3—C13—C15—C16	−90.3 (4)
C4—C5—C6—C7	−0.7 (6)	C10—C13—C15—C16	85.5 (4)
C5—C6—C7—C8	0.2 (6)	C13—C15—C16—C17	−179.2 (4)
C6—C7—C8—C3	0.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.91	2.616 (3)	138

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁ClN₄O
M_r	332.83
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	4.6700 (9), 11.647 (2), 16.064 (3)
α, β, γ (°)	78.56 (3), 86.75 (3), 79.81 (3)
V (Å³)	842.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.932, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	3470, 3061, 2353
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.182, 1.00
No. of reflections	3061
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.52

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.91	2.616 (3)	138.00

Acknowledgements

The authors thank the Innovation Fund for Doctoral Theses (BSCX200811) and Nanjing University of Technology for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Rajesh, K. & Joshi, Y. C. (2007). Arkivoc, pp. 142–149. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 10| October 2009| Page o2318

doi:10.1107/S1600536809033911

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

7-Chloro-5-(2-eth­oxy­phen­yl)-1-methyl-3-propyl-2,6-di­hydro-1H-pyrazolo[4,3-d]pyrimidine

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

7-Chloro-5-(2-ethoxyphenyl)-1-methyl-3-propyl-2,6-dihydro-1H-pyrazolo[4,3-d]pyrimidine