5-Butyl­amino-6-(4-fluoro­phen­yl)-7-oxo-1-p-tolyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidine-3-carbonitrile

Hu, J.-H.; Wu, M.-H.

doi:10.1107/S1600536808009744

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o845

doi:10.1107/S1600536808009744

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5-Butylamino-6-(4-fluorophenyl)-7-oxo-1-p-tolyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidine-3-carbonitrile

Ji-Huan Hu ^a and Ming-Hu Wu ^b ^*

^aCollege of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China, and ^bDepartment of Chemistry and Life Sciences, Xianning College, Xianning 437100, People's Republic of China
^*Correspondence e-mail: minghuwu@hotmail.com

(Received 3 March 2008; accepted 8 April 2008; online 16 April 2008)

In the title compound, C₂₃H₂₁FN₆O, the dihedral angle between the fluorophenyl and pyrimidinone rings is 75.9 (1)°, and the dihedral angle between the methylphenyl and pyrazole rings is 40.3 (1)°. In the crystal structure, weak C—H⋯π(arene) and C—N⋯π(arene) interactions and intermolecular C—H⋯N and N—H⋯O hydrogen-bonding interactions are present.

Related literature

For background information, see: Bell et al. (1991 ); Zhao et al. (2006 ); Allerton et al. (2006 ).

Experimental

Crystal data

C₂₃H₂₁FN₆O
M_r = 416.46
Monoclinic, P 2₁ /c
a = 11.8800 (5) Å
b = 9.36020 (4) Å
c = 19.0053 (8) Å
β = 91.178 (1)°
V = 2112.93 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.973, T_max = 0.982
12013 measured reflections
3704 independent reflections
3085 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.154
S = 1.11
3704 reflections
285 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 ring and Cg2 is the centroid of the N4/C9/C10/C13/N5/C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6A⋯O1ⁱ	0.861 (10)	2.32 (2)	2.904 (2)	125 (2)
C15—H15⋯N3ⁱⁱ	0.93	2.58	3.449 (3)	155
C19—H19⋯N3ⁱⁱⁱ	0.93	2.50	3.219 (3)	134
C6—H6⋯Cg1^iv	0.93	2.82	3.671 (2)	152
C11—N3⋯Cg2^v	1.141 (3)	3.621 (3)	3.710 (3)	85.4 (2)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y, -z; (iii) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) -x, -y, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009744/er2051sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009744/er2051Isup2.hkl

checkCIF report

Comment top

Pyrazolo[4,3-d]pyrimidin-7-ones have been reported as potent and selective inhibitors of PDE5 (Bell et al., 1991; Zhao et al., 2006). Sildenafil citrate, a pyrazolo[4,3-d]pyrimidin-7-one derivative, is the first orally effective PDE5 inhibitor approved for the treatment of erectile dysfunction. Its advent has spurred significant interest in the development of additional PDE5 inhibitors (Allerton et al., 2006). Herein, the title compound as Sildenafil analog was synthesized and determined by X-ray crystal diffraction in order to find new potent PDE5 inhibitors.

In the molecule (Fig. 1), the dihedral angle between the fluorophenyl and pyrimidinon ring is 75.9 (1)°, and the dihedral angle between the methylphenyl and pyrazole ring is 40.3 (1)°. The atoms O1, N1–N6, C5, C8–C14 and C20 are nearly coplanar, and N6, C21–C23 formed a plane.

In the crystal structure, molecules are linked by weak C—H···π (arene) interactions, which connected H6 to the centroid of atoms C14–19, Cg1, (symmetry code: -x,1/2 + y,1/2 - z). In addition, the crystal structure is stablized by intermolecular N—H···O and intramolecular C—H···N hydrogen-bonding interactions (Fig. 2).

Related literature top

For background information, see: Bell et al. (1991); Zhao et al. (2006); Allerton et al. (2006).

Experimental top

To a solution of 4-(3-cyano-5-ethoxycarbonyl-p-tolyl-1H-pyrazolyl) iminophosphorane (1.59 g, 3 mmol) in absolute anhydrous CH₂Cl₂, 4-fluorophenylisocyanate (3 mmol) was added at room temperature. The reaction mixture was left unstirred for 6 h at 273–278 K, whereafter a slight excess of butylamine (3.1 mmol) was added. After that, the reaction mixture was stirred for 6 h, the solution was cooled and the reaction product was recrystallized from EtOH and CH₂Cl₂ to give colorless crystals of the title compound in yield 93%, suitable for X-ray analysis.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. View of the molecule with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The packing viewed down the b axis. Intermolecular hydrogen bonds are shown as dashed lines.

5-Butylamino-6-(4-fluorophenyl)-7-oxo-1-p-tolyl-6,7-dihydro- 1H-pyrazolo[4,3-d]pyrimidine-3-carbonitrile top

Crystal data top

C₂₃H₂₁FN₆O	F(000) = 872
M_r = 416.46	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3510 reflections
a = 11.8800 (5) Å	θ = 2.4–23.9°
b = 9.36020 (4) Å	µ = 0.09 mm⁻¹
c = 19.0053 (8) Å	T = 295 K
β = 91.178 (1)°	Block, colourless
V = 2112.93 (13) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3704 independent reflections
Radiation source: fine-focus sealed tube	3085 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −14→14
T_min = 0.973, T_max = 0.982	k = −11→11
12013 measured reflections	l = −16→22

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0811P)² + 0.4221P] where P = (F_o² + 2F_c²)/3
3704 reflections	(Δ/σ)_max < 0.001
285 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₃H₂₁FN₆O	V = 2112.93 (13) Å³
M_r = 416.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.8800 (5) Å	µ = 0.09 mm⁻¹
b = 9.36020 (4) Å	T = 295 K
c = 19.0053 (8) Å	0.30 × 0.20 × 0.20 mm
β = 91.178 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	3704 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3085 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.982	R_int = 0.031
12013 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	1 restraint
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.23 e Å⁻³
3704 reflections	Δρ_min = −0.26 e Å⁻³
285 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
C1	0.6274 (2)	0.3875 (3)	0.22154 (16)	0.0778 (9)
H1A	0.6429	0.3528	0.2683	0.117*
H1B	0.6068	0.4865	0.2236	0.117*
H1C	0.6934	0.3769	0.1937	0.117*
C2	0.53165 (19)	0.3027 (3)	0.18861 (12)	0.0517 (6)
C3	0.55219 (19)	0.1809 (3)	0.15018 (14)	0.0614 (7)
H3	0.6261	0.1512	0.1443	0.074*
C4	0.46540 (18)	0.1021 (3)	0.12017 (14)	0.0552 (6)
H4	0.4809	0.0204	0.0942	0.066*
C5	0.35615 (17)	0.1450 (2)	0.12887 (11)	0.0399 (5)
C6	0.33266 (18)	0.2674 (2)	0.16595 (12)	0.0473 (6)
H6	0.2587	0.2978	0.1708	0.057*
C7	0.4207 (2)	0.3443 (2)	0.19588 (13)	0.0525 (6)
H7	0.4049	0.4262	0.2216	0.063*
C8	0.18880 (17)	−0.0696 (2)	0.01909 (11)	0.0406 (5)
C9	0.11084 (16)	−0.0625 (2)	0.07421 (10)	0.0362 (5)
C10	0.16433 (16)	0.0224 (2)	0.12452 (11)	0.0361 (5)
C11	0.17644 (18)	−0.1440 (3)	−0.04584 (12)	0.0468 (6)
C12	−0.03810 (16)	−0.1084 (2)	0.14132 (11)	0.0371 (5)
C13	0.11533 (16)	0.0439 (2)	0.19173 (11)	0.0368 (5)
C14	−0.04608 (16)	−0.0095 (2)	0.26283 (10)	0.0378 (5)
C15	−0.13358 (18)	0.0858 (2)	0.26853 (12)	0.0465 (5)
H15	−0.1606	0.1347	0.2291	0.056*
C16	−0.1812 (2)	0.1083 (3)	0.33376 (13)	0.0533 (6)
H16	−0.2413	0.1709	0.3384	0.064*
C17	−0.1383 (2)	0.0369 (3)	0.39086 (12)	0.0544 (6)
C18	−0.0514 (2)	−0.0580 (3)	0.38634 (12)	0.0555 (6)
H18	−0.0241	−0.1056	0.4261	0.067*
C19	−0.00515 (19)	−0.0814 (2)	0.32127 (12)	0.0481 (6)
H19	0.0538	−0.1459	0.3168	0.058*
C20	−0.19690 (18)	−0.2591 (2)	0.10305 (12)	0.0466 (5)
H20A	−0.1732	−0.3570	0.1113	0.056*
H20B	−0.1764	−0.2329	0.0556	0.056*
C21	−0.32235 (19)	−0.2480 (3)	0.11024 (13)	0.0523 (6)
H21A	−0.3451	−0.1499	0.1017	0.063*
H21B	−0.3416	−0.2719	0.1582	0.063*
C22	−0.3878 (2)	−0.3448 (3)	0.06021 (15)	0.0654 (7)
H22A	−0.3655	−0.4430	0.0689	0.078*
H22B	−0.3684	−0.3214	0.0123	0.078*
C23	−0.5142 (2)	−0.3322 (4)	0.0676 (2)	0.1029 (13)
H23A	−0.5328	−0.3385	0.1164	0.154*
H23B	−0.5507	−0.4081	0.0420	0.154*
H23C	−0.5392	−0.2419	0.0491	0.154*
F1	−0.18395 (16)	0.0621 (2)	0.45430 (8)	0.0869 (6)
N1	0.26695 (13)	0.06138 (18)	0.09789 (9)	0.0396 (4)
N2	0.28234 (14)	0.0051 (2)	0.03381 (9)	0.0437 (5)
N3	0.16543 (19)	−0.2048 (3)	−0.09756 (11)	0.0671 (6)
N4	0.00947 (14)	−0.12733 (18)	0.08064 (9)	0.0386 (4)
N5	0.01053 (13)	−0.02716 (18)	0.19646 (8)	0.0373 (4)
N6	−0.13968 (15)	−0.1649 (2)	0.15346 (9)	0.0452 (5)
H6A	−0.1566 (19)	−0.175 (3)	0.1970 (6)	0.054*
O1	0.15378 (12)	0.11047 (17)	0.24170 (8)	0.0502 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0649 (18)	0.080 (2)	0.087 (2)	−0.0194 (15)	−0.0151 (16)	−0.0128 (16)
C2	0.0469 (13)	0.0553 (14)	0.0527 (14)	−0.0113 (11)	−0.0035 (10)	0.0014 (11)
C3	0.0333 (12)	0.0704 (17)	0.0807 (19)	−0.0020 (11)	0.0045 (12)	−0.0152 (14)
C4	0.0386 (12)	0.0573 (15)	0.0698 (17)	−0.0003 (10)	0.0073 (11)	−0.0186 (12)
C5	0.0375 (11)	0.0428 (12)	0.0395 (12)	−0.0042 (9)	0.0018 (9)	0.0025 (9)
C6	0.0379 (11)	0.0435 (12)	0.0605 (14)	0.0020 (9)	0.0013 (10)	0.0014 (11)
C7	0.0520 (14)	0.0427 (13)	0.0628 (15)	−0.0041 (10)	0.0031 (11)	−0.0073 (11)
C8	0.0373 (11)	0.0505 (12)	0.0340 (11)	−0.0020 (9)	0.0000 (9)	0.0006 (9)
C9	0.0353 (10)	0.0389 (11)	0.0344 (11)	0.0006 (8)	−0.0018 (8)	0.0031 (9)
C10	0.0330 (10)	0.0376 (11)	0.0377 (11)	0.0011 (8)	0.0004 (8)	0.0013 (9)
C11	0.0417 (12)	0.0613 (14)	0.0375 (13)	−0.0070 (10)	0.0064 (9)	0.0005 (11)
C12	0.0357 (11)	0.0395 (11)	0.0359 (12)	−0.0004 (8)	−0.0031 (9)	0.0030 (9)
C13	0.0337 (10)	0.0394 (11)	0.0372 (11)	0.0023 (8)	−0.0025 (8)	−0.0008 (9)
C14	0.0347 (10)	0.0422 (11)	0.0365 (11)	−0.0046 (9)	0.0012 (8)	−0.0023 (9)
C15	0.0422 (12)	0.0484 (13)	0.0490 (14)	−0.0015 (10)	0.0025 (10)	0.0043 (10)
C16	0.0468 (13)	0.0523 (14)	0.0615 (16)	0.0020 (10)	0.0162 (11)	−0.0049 (12)
C17	0.0598 (15)	0.0617 (15)	0.0423 (14)	−0.0120 (12)	0.0157 (11)	−0.0092 (12)
C18	0.0569 (15)	0.0720 (16)	0.0376 (13)	−0.0013 (12)	0.0001 (10)	0.0037 (12)
C19	0.0466 (12)	0.0561 (14)	0.0418 (13)	0.0063 (10)	0.0014 (10)	0.0032 (10)
C20	0.0452 (12)	0.0517 (13)	0.0430 (13)	−0.0091 (10)	−0.0007 (10)	−0.0018 (10)
C21	0.0459 (13)	0.0547 (14)	0.0561 (15)	−0.0105 (11)	0.0009 (11)	−0.0026 (11)
C22	0.0543 (15)	0.0717 (18)	0.0700 (17)	−0.0164 (13)	−0.0053 (13)	−0.0101 (14)
C23	0.0517 (17)	0.104 (3)	0.152 (3)	−0.0189 (17)	−0.0184 (19)	−0.032 (2)
F1	0.0979 (12)	0.1106 (14)	0.0536 (10)	0.0002 (10)	0.0339 (9)	−0.0121 (9)
N1	0.0336 (9)	0.0448 (10)	0.0405 (10)	−0.0028 (7)	0.0036 (7)	−0.0026 (8)
N2	0.0391 (10)	0.0533 (11)	0.0390 (10)	−0.0034 (8)	0.0039 (8)	−0.0027 (8)
N3	0.0729 (15)	0.0862 (16)	0.0425 (12)	−0.0188 (12)	0.0066 (10)	−0.0109 (12)
N4	0.0366 (9)	0.0445 (10)	0.0346 (10)	−0.0043 (7)	−0.0011 (7)	0.0006 (7)
N5	0.0342 (9)	0.0461 (10)	0.0316 (9)	−0.0027 (7)	0.0016 (7)	−0.0008 (7)
N6	0.0430 (10)	0.0552 (11)	0.0374 (10)	−0.0145 (8)	0.0036 (8)	−0.0004 (9)
O1	0.0453 (9)	0.0611 (10)	0.0442 (9)	−0.0109 (7)	0.0015 (7)	−0.0139 (7)

Geometric parameters (Å, º) top

C1—C2	1.512 (3)	C14—C15	1.375 (3)
C1—H1A	0.9600	C14—C19	1.379 (3)
C1—H1B	0.9600	C14—N5	1.451 (3)
C1—H1C	0.9600	C15—C16	1.389 (3)
C2—C3	1.379 (3)	C15—H15	0.9300
C2—C7	1.384 (3)	C16—C17	1.364 (3)
C3—C4	1.382 (3)	C16—H16	0.9300
C3—H3	0.9300	C17—F1	1.353 (3)
C4—C5	1.372 (3)	C17—C18	1.366 (3)
C4—H4	0.9300	C18—C19	1.381 (3)
C5—C6	1.376 (3)	C18—H18	0.9300
C5—N1	1.434 (3)	C19—H19	0.9300
C6—C7	1.382 (3)	C20—N6	1.460 (3)
C6—H6	0.9300	C20—C21	1.503 (3)
C7—H7	0.9300	C20—H20A	0.9700
C8—N2	1.338 (3)	C20—H20B	0.9700
C8—C9	1.414 (3)	C21—C22	1.516 (3)
C8—C11	1.422 (3)	C21—H21A	0.9700
C9—N4	1.356 (3)	C21—H21B	0.9700
C9—C10	1.387 (3)	C22—C23	1.516 (4)
C10—N1	1.379 (2)	C22—H22A	0.9700
C10—C13	1.429 (3)	C22—H22B	0.9700
C11—N3	1.141 (3)	C23—H23A	0.9600
C12—N4	1.307 (3)	C23—H23B	0.9600
C12—N6	1.342 (3)	C23—H23C	0.9600
C12—N5	1.409 (3)	N1—N2	1.343 (2)
C13—O1	1.217 (2)	N6—H6A	0.861 (10)
C13—N5	1.416 (3)

C2—C1—H1A	109.5	C17—C16—H16	120.5
C2—C1—H1B	109.5	C15—C16—H16	120.5
H1A—C1—H1B	109.5	F1—C17—C16	118.2 (2)
C2—C1—H1C	109.5	F1—C17—C18	119.1 (2)
H1A—C1—H1C	109.5	C16—C17—C18	122.6 (2)
H1B—C1—H1C	109.5	C17—C18—C19	118.3 (2)
C3—C2—C7	117.7 (2)	C17—C18—H18	120.8
C3—C2—C1	120.9 (2)	C19—C18—H18	120.8
C7—C2—C1	121.4 (2)	C14—C19—C18	120.2 (2)
C2—C3—C4	121.5 (2)	C14—C19—H19	119.9
C2—C3—H3	119.3	C18—C19—H19	119.9
C4—C3—H3	119.3	N6—C20—C21	110.36 (18)
C5—C4—C3	119.6 (2)	N6—C20—H20A	109.6
C5—C4—H4	120.2	C21—C20—H20A	109.6
C3—C4—H4	120.2	N6—C20—H20B	109.6
C4—C5—C6	120.5 (2)	C21—C20—H20B	109.6
C4—C5—N1	118.90 (19)	H20A—C20—H20B	108.1
C6—C5—N1	120.57 (18)	C20—C21—C22	113.5 (2)
C5—C6—C7	119.0 (2)	C20—C21—H21A	108.9
C5—C6—H6	120.5	C22—C21—H21A	108.9
C7—C6—H6	120.5	C20—C21—H21B	108.9
C6—C7—C2	121.8 (2)	C22—C21—H21B	108.9
C6—C7—H7	119.1	H21A—C21—H21B	107.7
C2—C7—H7	119.1	C21—C22—C23	113.0 (2)
N2—C8—C9	111.97 (18)	C21—C22—H22A	109.0
N2—C8—C11	120.53 (19)	C23—C22—H22A	109.0
C9—C8—C11	127.50 (19)	C21—C22—H22B	109.0
N4—C9—C10	126.10 (19)	C23—C22—H22B	109.0
N4—C9—C8	129.92 (18)	H22A—C22—H22B	107.8
C10—C9—C8	103.89 (17)	C22—C23—H23A	109.5
N1—C10—C9	107.14 (17)	C22—C23—H23B	109.5
N1—C10—C13	132.08 (18)	H23A—C23—H23B	109.5
C9—C10—C13	120.51 (18)	C22—C23—H23C	109.5
N3—C11—C8	179.1 (3)	H23A—C23—H23C	109.5
N4—C12—N6	120.35 (18)	H23B—C23—H23C	109.5
N4—C12—N5	123.46 (17)	N2—N1—C10	111.51 (16)
N6—C12—N5	116.17 (18)	N2—N1—C5	118.25 (16)
O1—C13—N5	120.49 (18)	C10—N1—C5	130.19 (17)
O1—C13—C10	128.07 (19)	C8—N2—N1	105.48 (16)
N5—C13—C10	111.42 (16)	C12—N4—C9	114.82 (17)
C15—C14—C19	120.5 (2)	C12—N5—C13	123.64 (16)
C15—C14—N5	120.46 (18)	C12—N5—C14	121.19 (16)
C19—C14—N5	118.84 (18)	C13—N5—C14	115.17 (15)
C14—C15—C16	119.4 (2)	C12—N6—C20	122.23 (18)
C14—C15—H15	120.3	C12—N6—H6A	116.0 (16)
C16—C15—H15	120.3	C20—N6—H6A	116.6 (16)
C17—C16—C15	118.9 (2)

C7—C2—C3—C4	−0.4 (4)	N6—C20—C21—C22	−179.1 (2)
C1—C2—C3—C4	179.6 (3)	C20—C21—C22—C23	−179.7 (3)
C2—C3—C4—C5	−0.3 (4)	C9—C10—N1—N2	−0.6 (2)
C3—C4—C5—C6	1.3 (4)	C13—C10—N1—N2	173.4 (2)
C3—C4—C5—N1	−179.5 (2)	C9—C10—N1—C5	−178.14 (19)
C4—C5—C6—C7	−1.7 (3)	C13—C10—N1—C5	−4.2 (4)
N1—C5—C6—C7	179.2 (2)	C4—C5—N1—N2	−38.9 (3)
C5—C6—C7—C2	1.0 (4)	C6—C5—N1—N2	140.2 (2)
C3—C2—C7—C6	0.0 (4)	C4—C5—N1—C10	138.4 (2)
C1—C2—C7—C6	−180.0 (2)	C6—C5—N1—C10	−42.4 (3)
N2—C8—C9—N4	−177.1 (2)	C9—C8—N2—N1	0.0 (2)
C11—C8—C9—N4	3.1 (4)	C11—C8—N2—N1	179.83 (19)
N2—C8—C9—C10	−0.3 (2)	C10—N1—N2—C8	0.4 (2)
C11—C8—C9—C10	179.8 (2)	C5—N1—N2—C8	178.24 (17)
N4—C9—C10—N1	177.48 (18)	N6—C12—N4—C9	178.61 (18)
C8—C9—C10—N1	0.6 (2)	N5—C12—N4—C9	0.1 (3)
N4—C9—C10—C13	2.7 (3)	C10—C9—N4—C12	−1.8 (3)
C8—C9—C10—C13	−174.26 (18)	C8—C9—N4—C12	174.3 (2)
N2—C8—C11—N3	159 (18)	N4—C12—N5—C13	0.7 (3)
C9—C8—C11—N3	−21 (18)	N6—C12—N5—C13	−177.79 (18)
N1—C10—C13—O1	3.8 (4)	N4—C12—N5—C14	179.94 (18)
C9—C10—C13—O1	177.1 (2)	N6—C12—N5—C14	1.4 (3)
N1—C10—C13—N5	−174.8 (2)	O1—C13—N5—C12	−178.73 (18)
C9—C10—C13—N5	−1.5 (3)	C10—C13—N5—C12	0.0 (3)
C19—C14—C15—C16	−0.5 (3)	O1—C13—N5—C14	2.0 (3)
N5—C14—C15—C16	−175.46 (19)	C10—C13—N5—C14	−179.23 (16)
C14—C15—C16—C17	1.2 (3)	C15—C14—N5—C12	−78.0 (2)
C15—C16—C17—F1	178.7 (2)	C19—C14—N5—C12	106.9 (2)
C15—C16—C17—C18	−1.2 (4)	C15—C14—N5—C13	101.2 (2)
F1—C17—C18—C19	−179.4 (2)	C19—C14—N5—C13	−73.8 (2)
C16—C17—C18—C19	0.4 (4)	N4—C12—N6—C20	5.5 (3)
C15—C14—C19—C18	−0.3 (3)	N5—C12—N6—C20	−175.88 (18)
N5—C14—C19—C18	174.8 (2)	C21—C20—N6—C12	−152.0 (2)
C17—C18—C19—C14	0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O1ⁱ	0.86 (1)	2.32 (2)	2.904 (2)	125 (2)
C15—H15···N3ⁱⁱ	0.93	2.58	3.449 (3)	155
C19—H19···N3ⁱⁱⁱ	0.93	2.50	3.219 (3)	134
C6—H6···Cg1^iv	0.93	2.82	3.671 (2)	152

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₁FN₆O
M_r	416.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	11.8800 (5), 9.36020 (4), 19.0053 (8)
β (°)	91.178 (1)
V (Å³)	2112.93 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.973, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	12013, 3704, 3085
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.154, 1.11
No. of reflections	3704
No. of parameters	285
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O1ⁱ	0.861 (10)	2.32 (2)	2.904 (2)	125 (2)
C15—H15···N3ⁱⁱ	0.93	2.58	3.449 (3)	154.9
C19—H19···N3ⁱⁱⁱ	0.93	2.50	3.219 (3)	133.9
C6—H6···Cg1^iv	0.93	2.82	3.671 (2)	152

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

Acknowledgements

The authors gratefully acknowledge financial support of this work as a project of the Natural Science Foundation of Hubei Province under grant No. 2006ABA334.

References

Allerton, C. M. N., Barber, C. G., Beaumont, K. C., Brown, D. G., Cole, S. M., Ellis, D., Lane, C. A. L., Maw, G. N., Mount, N. M., Rawson, D. J., Robinson, C. M., Street, S. D. A. & Summerhill, N. W. (2006). J. Med. Chem. 49, 3581–3594. Web of Science CrossRef PubMed CAS Google Scholar
Bell, A. S., Brown, D. & Terrett, N. K. (1991). Eur. Patent 463756. Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, Y., Zhai, X., Chen, J., Guo, S. & Gong, P. (2006). Chem. Res. Chin. Univ. 22, 468–473. Web of Science CrossRef CAS Google Scholar

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Volume 64| Part 5| May 2008| Page o845

doi:10.1107/S1600536808009744

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

5-Butyl­amino-6-(4-fluoro­phen­yl)-7-oxo-1-p-tolyl-6,7-di­hydro-1H-pyrazolo[4,3-d]pyrimidine-3-carbo­nitrile

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5-Butylamino-6-(4-fluorophenyl)-7-oxo-1-p-tolyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidine-3-carbonitrile