Ethyl 3-(4-fluoro­phen­yl)-6-methyl-4-oxo-2-(1-cyclohexylamino)-3,4-dihydro­furo[2,3-d]pyrimidine-5-carboxyl­ate

Sun, Y.; Zeng, G.-P.; Hu, Y.-G.

doi:10.1107/S1600536807066780

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Pages o311-o312

https://doi.org/10.1107/S1600536807066780

Open

access

Ethyl 3-(4-fluorophenyl)-6-methyl-4-oxo-2-(1-cyclohexylamino)-3,4-dihydrofuro[2,3-d]pyrimidine-5-carboxylate

Yong Sun,^a ^* Guo-Ping Zeng ^b and Yang-Gen Hu ^c,^d

^aYunyang Teachers College, Danjiangkou 442700, People's Republic of China, ^bDepartment of Chemistry and Life Science, Hubei University of Education, Wuhan 430205, People's Republic of China, ^cKey Laboratory of Pesticides and Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079, People's Republic of China, and ^d Department of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China
^*Correspondence e-mail: suny6135@126.com

(Received 4 December 2007; accepted 13 December 2007; online 21 December 2007)

In the crystal structure of the title compound, C₂₂H₂₄FN₃O₄, the two fused rings of furo[2,3-d]pyrimidine form a dihedral angle of 0.88 (13)°. The attached benzene ring is twisted with respect to the heterocyclic pyrimidinone ring, making a dihedral angle of 75.07 (12)°. The cyclohexyl ring shows a distorted chair conformation. The molecular structure is stabilized by intramolecular C—H⋯O and C—H⋯N hydrogen-bonding interactions. The crystal packing is mainly stabilized by C—H⋯π hydrogen-bond interactions. Further stability is provided by C—F⋯π and C—O⋯π stacking interactions.

Related literature

The preparation and biological activity are described by Miyazaki et al. (2007 ), Gangjee et al. (2006 ) and Lagu et al. (2000 ). For related literature, see: Ding et al. (2004 ). For the crystal structure of another fused pyrimidinone derivative, see: Hu et al. (2007 ).

Experimental

Crystal data

C₂₂H₂₄FN₃O₄
M_r = 413.44
Triclinic, $[P \overline 1]$
a = 9.2051 (8) Å
b = 10.7957 (9) Å
c = 11.6601 (10) Å
α = 106.681 (1)°
β = 100.417 (2)°
γ = 101.550 (2)°
V = 1051.85 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 291 (2) K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.972, T_max = 0.981
10785 measured reflections
4505 independent reflections
2941 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.182
S = 1.09
4505 reflections
276 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond and C—F⋯π and C—O⋯π interactions (Å, °)

Cg2 and Cg3 are the centroids of the N1/C9/C7/C8/N2/C10 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯N2	0.98	2.41	2.813 (3)	104
C6—H6A⋯O2	0.96	2.45	3.039 (3)	120
C20—H20B⋯Cg3ⁱ	0.97	2.97	3.820 (4)	147
C14—F1⋯Cg3ⁱⁱ	1.36 (1)	3.36 (1)	3.732 (3)	95
C3—O2⋯Cg2ⁱⁱⁱ	1.21 (1)	3.31 (1)	3.409 (3)	84

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2001 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807066780/at2523sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807066780/at2523Isup2.hkl

checkCIF report

Comment top

Fused pyrimidine compounds are valued not only for their rich and varied chemistry, but also for many important biological properties. Among them, the furopyrimidine ring system, because of a formal isoelectronic relationship with purine, is of special biological interest (Miyazaki et al., 2007; Gangjee et al. 2006; Lagu et al., 2000). Recently, we have focused on the synthesis of the heterocycle systems containing fused furopyrimidine via aza-Wittig reaction at room temperature (Hu, et al., 2007). Herein, we present X-ray crystallographic analysis of the compound (I) in this paper,(Fig. 1), which may be used as a new precursor for obtaining bioactive molecules.

In the molecule (I), the bond lengths and angles are unexceptional. The two fused rings of furo[2,3-d]pyrimidine form a dihedral angle of 0.88 (13)°. The C11—C16 phenyl ring is twisted with respect to pyrimidinone ring, with a dihedral angle of 75.07 (1)°. The cyclohexyl ring in (I) shows a distored chair conformation [φ =30.0 (3)° and θ = 2.5 (3)°, puckering amplitude = 0.557 (3) Å]. The molecular structure is stabilized by intramolecular C—H···O and C—H···N hydrogen bonds interactions (Table 1). The crystal packing is mainly stabilized by C—H···π hydrogen bonding interactions. Further stability is provided by C—F···π and C—O···π stacking interactions.

Related literature top

The preparation and biological activity are described by Miyazaki et al. (2007), Gangjee et al. (2006) and Lagu et al. (2000). For related literature, see: Ding et al. (2004). For the crystal structure of another fused pyrimidinone derivative, see: Hu et al. (2007).

Experimental top

To a solution of the diethyl 2-((4-fluorophenylimino)methyleneamino)-5-methylfuran- 3,4-dicarboxylate (3 mmol) in dichloromethane (5 ml) was added cyclohexanamine (3 mmol). After stirring the reaction mixture for 1 h, the solvent was removed and anhydrous ethanol (10 ml) with several drops of EtONa in EtOH was added. The mixture was stirred for 3 h at room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give the title compound in a yield of 84%. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:1 v/v) at room temperature.

Structure description top

The preparation and biological activity are described by Miyazaki et al. (2007), Gangjee et al. (2006) and Lagu et al. (2000). For related literature, see: Ding et al. (2004). For the crystal structure of another fused pyrimidinone derivative, see: Hu et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top

	Fig. 1. The molecular structure of the title compound (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. Only the intramolecular C—H···O and C—H···N hydrogen bonds is shown as dashed lines.
	Fig. 2. A view of the packing and hydrogen bonding interactions of (I).

Ethyl 3-(4-fluorophenyl)-6-methyl-4-oxo- 2-(1-cyclohexylamino)-3,4-dihydrofuro[2,3-d]pyrimidine-5-carboxylate top

Crystal data top

C₂₂H₂₄FN₃O₄	Z = 2
M_r = 413.44	F(000) = 436
Triclinic, P1	D_x = 1.305 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2051 (8) Å	Cell parameters from 1930 reflections
b = 10.7957 (9) Å	θ = 2.3–22.7°
c = 11.6601 (10) Å	µ = 0.10 mm⁻¹
α = 106.681 (1)°	T = 291 K
β = 100.417 (2)°	Block, colourless
γ = 101.550 (2)°	0.30 × 0.30 × 0.20 mm
V = 1051.85 (16) Å³

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	4505 independent reflections
Radiation source: fine-focus sealed tube	2941 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −11→11
T_min = 0.972, T_max = 0.981	k = −13→13
10785 measured reflections	l = −14→14

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.084P)² + 0.0618P] where P = (F_o² + 2F_c²)/3
4505 reflections	(Δ/σ)_max = 0.001
276 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₂H₂₄FN₃O₄	γ = 101.550 (2)°
M_r = 413.44	V = 1051.85 (16) Å³
Triclinic, P1	Z = 2
a = 9.2051 (8) Å	Mo Kα radiation
b = 10.7957 (9) Å	µ = 0.10 mm⁻¹
c = 11.6601 (10) Å	T = 291 K
α = 106.681 (1)°	0.30 × 0.30 × 0.20 mm
β = 100.417 (2)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	4505 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2941 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.981	R_int = 0.036
10785 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.182	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.27 e Å⁻³
4505 reflections	Δρ_min = −0.21 e Å⁻³
276 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	0.3069 (4)	1.3641 (3)	0.4580 (4)	0.0893 (11)
H1A	0.2011	1.3243	0.4505	0.134*
H1B	0.3160	1.4451	0.4379	0.134*
H1C	0.3651	1.3846	0.5413	0.134*
C2	0.3654 (4)	1.2701 (3)	0.3728 (3)	0.0611 (8)
H2A	0.3083	1.2498	0.2881	0.073*
H2B	0.4726	1.3091	0.3800	0.073*
C3	0.3773 (3)	1.0444 (2)	0.3310 (2)	0.0405 (6)
C4	0.3423 (3)	0.9266 (2)	0.37091 (19)	0.0382 (5)
C5	0.3652 (3)	0.8068 (3)	0.3117 (2)	0.0436 (6)
C6	0.4214 (4)	0.7543 (3)	0.2014 (2)	0.0621 (8)
H6A	0.4101	0.8081	0.1494	0.093*
H6B	0.3631	0.6632	0.1563	0.093*
H6C	0.5276	0.7573	0.2269	0.093*
C7	0.2826 (2)	0.9094 (2)	0.47482 (18)	0.0346 (5)
C8	0.2770 (3)	0.7808 (2)	0.46902 (19)	0.0388 (5)
C9	0.2328 (3)	0.9897 (2)	0.5730 (2)	0.0404 (6)
C10	0.1892 (3)	0.7846 (2)	0.6342 (2)	0.0402 (6)
C11	0.1584 (3)	0.9935 (2)	0.76523 (19)	0.0372 (5)
C12	0.0208 (3)	1.0263 (2)	0.7601 (2)	0.0433 (6)
H12	−0.0514	1.0000	0.6847	0.052*
C13	−0.0090 (3)	1.0983 (3)	0.8672 (2)	0.0486 (6)
H13	−0.1013	1.1213	0.8653	0.058*
C14	0.0991 (3)	1.1353 (2)	0.9765 (2)	0.0480 (6)
C15	0.2366 (3)	1.1045 (3)	0.9847 (2)	0.0512 (7)
H15	0.3080	1.1311	1.0605	0.061*
C16	0.2661 (3)	1.0329 (2)	0.8772 (2)	0.0442 (6)
H16	0.3591	1.0110	0.8798	0.053*
C17	0.1711 (3)	0.6040 (2)	0.7262 (2)	0.0482 (6)
H17	0.1861	0.5517	0.6475	0.058*
C18	0.0384 (3)	0.5200 (3)	0.7535 (3)	0.0711 (9)
H18A	−0.0525	0.4956	0.6862	0.085*
H18B	0.0175	0.5719	0.8286	0.085*
C19	0.0750 (4)	0.3927 (3)	0.7692 (3)	0.0855 (11)
H19A	−0.0089	0.3431	0.7918	0.103*
H19B	0.0843	0.3362	0.6910	0.103*
C22	0.3165 (3)	0.6368 (3)	0.8250 (3)	0.0721 (9)
H22A	0.3063	0.6937	0.9027	0.087*
H22B	0.4009	0.6863	0.8028	0.087*
C21	0.3524 (4)	0.5105 (4)	0.8417 (4)	0.0887 (11)
H21A	0.3757	0.4594	0.7675	0.106*
H21B	0.4423	0.5356	0.9100	0.106*
F1	0.0682 (2)	1.20612 (17)	1.08220 (14)	0.0762 (5)
N1	0.1902 (2)	0.91680 (18)	0.65370 (16)	0.0378 (5)
N2	0.2326 (2)	0.71226 (19)	0.54199 (17)	0.0446 (5)
N3	0.1374 (3)	0.7269 (2)	0.71300 (19)	0.0498 (6)
H3	0.117 (3)	0.781 (3)	0.774 (2)	0.060*
O1	0.3480 (2)	1.14890 (17)	0.40502 (15)	0.0509 (5)
O2	0.4260 (2)	1.04606 (19)	0.24179 (15)	0.0588 (5)
O3	0.32637 (19)	0.71581 (16)	0.37123 (14)	0.0467 (4)
O4	0.2239 (2)	1.10393 (18)	0.59732 (17)	0.0639 (6)
C20	0.2211 (4)	0.4244 (3)	0.8669 (3)	0.0785 (10)
H20A	0.2073	0.4705	0.9472	0.094*
H20B	0.2447	0.3414	0.8694	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.116 (3)	0.060 (2)	0.113 (3)	0.040 (2)	0.051 (2)	0.036 (2)
C2	0.078 (2)	0.0520 (18)	0.0698 (18)	0.0230 (15)	0.0288 (15)	0.0349 (15)
C3	0.0412 (13)	0.0461 (15)	0.0371 (12)	0.0116 (11)	0.0116 (10)	0.0170 (11)
C4	0.0408 (13)	0.0407 (14)	0.0353 (11)	0.0116 (11)	0.0115 (10)	0.0144 (10)
C5	0.0492 (15)	0.0439 (15)	0.0394 (12)	0.0130 (12)	0.0139 (11)	0.0143 (11)
C6	0.087 (2)	0.0552 (18)	0.0517 (15)	0.0236 (16)	0.0370 (15)	0.0135 (13)
C7	0.0377 (12)	0.0329 (13)	0.0336 (11)	0.0083 (10)	0.0088 (9)	0.0128 (9)
C8	0.0445 (13)	0.0371 (13)	0.0334 (11)	0.0116 (11)	0.0092 (10)	0.0095 (10)
C9	0.0524 (15)	0.0373 (14)	0.0413 (12)	0.0160 (11)	0.0189 (11)	0.0208 (11)
C10	0.0493 (14)	0.0361 (14)	0.0413 (12)	0.0132 (11)	0.0141 (11)	0.0191 (11)
C11	0.0491 (14)	0.0311 (13)	0.0392 (12)	0.0116 (11)	0.0180 (10)	0.0187 (10)
C12	0.0499 (15)	0.0432 (14)	0.0465 (13)	0.0154 (12)	0.0194 (11)	0.0233 (11)
C13	0.0530 (16)	0.0496 (16)	0.0607 (16)	0.0240 (13)	0.0294 (13)	0.0286 (13)
C14	0.0699 (18)	0.0384 (14)	0.0444 (13)	0.0172 (13)	0.0284 (12)	0.0167 (11)
C15	0.0608 (17)	0.0560 (17)	0.0397 (13)	0.0137 (14)	0.0151 (12)	0.0201 (12)
C16	0.0469 (14)	0.0488 (15)	0.0457 (13)	0.0179 (12)	0.0162 (11)	0.0225 (12)
C17	0.0732 (18)	0.0363 (14)	0.0472 (13)	0.0219 (13)	0.0229 (12)	0.0224 (11)
C18	0.066 (2)	0.0461 (17)	0.107 (2)	0.0083 (14)	0.0117 (17)	0.0453 (18)
C19	0.094 (3)	0.0490 (19)	0.118 (3)	0.0104 (17)	0.013 (2)	0.049 (2)
C22	0.064 (2)	0.067 (2)	0.094 (2)	0.0068 (16)	0.0143 (17)	0.0515 (18)
C21	0.083 (2)	0.095 (3)	0.114 (3)	0.033 (2)	0.017 (2)	0.072 (2)
F1	0.1084 (14)	0.0745 (12)	0.0571 (9)	0.0383 (10)	0.0431 (9)	0.0164 (8)
N1	0.0501 (12)	0.0334 (11)	0.0378 (9)	0.0148 (9)	0.0169 (8)	0.0176 (8)
N2	0.0613 (13)	0.0339 (11)	0.0444 (11)	0.0145 (10)	0.0197 (10)	0.0164 (9)
N3	0.0759 (16)	0.0355 (13)	0.0520 (12)	0.0212 (11)	0.0302 (11)	0.0228 (10)
O1	0.0728 (12)	0.0399 (10)	0.0524 (10)	0.0168 (9)	0.0321 (9)	0.0228 (8)
O2	0.0806 (14)	0.0645 (13)	0.0517 (10)	0.0286 (10)	0.0368 (10)	0.0311 (9)
O3	0.0627 (11)	0.0374 (10)	0.0440 (9)	0.0158 (8)	0.0218 (8)	0.0128 (8)
O4	0.1135 (16)	0.0423 (11)	0.0695 (12)	0.0402 (11)	0.0578 (11)	0.0346 (9)
C20	0.104 (3)	0.070 (2)	0.086 (2)	0.032 (2)	0.0246 (19)	0.0550 (19)

Geometric parameters (Å, º) top

C1—C2	1.463 (4)	C12—C13	1.375 (3)
C1—H1A	0.9600	C12—H12	0.9300
C1—H1B	0.9600	C13—C14	1.365 (4)
C1—H1C	0.9600	C13—H13	0.9300
C2—O1	1.449 (3)	C14—F1	1.363 (3)
C2—H2A	0.9700	C14—C15	1.365 (4)
C2—H2B	0.9700	C15—C16	1.377 (3)
C3—O2	1.208 (3)	C15—H15	0.9300
C3—O1	1.318 (3)	C16—H16	0.9300
C3—C4	1.472 (3)	C17—N3	1.464 (3)
C4—C5	1.357 (3)	C17—C22	1.505 (4)
C4—C7	1.461 (3)	C17—C18	1.509 (4)
C5—O3	1.384 (3)	C17—H17	0.9800
C5—C6	1.478 (3)	C18—C19	1.531 (4)
C6—H6A	0.9600	C18—H18A	0.9700
C6—H6B	0.9600	C18—H18B	0.9700
C6—H6C	0.9600	C19—C20	1.504 (4)
C7—C8	1.361 (3)	C19—H19A	0.9700
C7—C9	1.432 (3)	C19—H19B	0.9700
C8—N2	1.343 (3)	C22—C21	1.522 (4)
C8—O3	1.362 (3)	C22—H22A	0.9700
C9—O4	1.207 (3)	C22—H22B	0.9700
C9—N1	1.446 (3)	C21—C20	1.498 (5)
C10—N2	1.313 (3)	C21—H21A	0.9700
C10—N3	1.352 (3)	C21—H21B	0.9700
C10—N1	1.377 (3)	N3—H3	0.86 (3)
C11—C12	1.378 (3)	C20—H20A	0.9700
C11—C16	1.383 (3)	C20—H20B	0.9700
C11—N1	1.442 (3)

C2—C1—H1A	109.5	C14—C15—C16	117.9 (2)
C2—C1—H1B	109.5	C14—C15—H15	121.1
H1A—C1—H1B	109.5	C16—C15—H15	121.1
C2—C1—H1C	109.5	C15—C16—C11	120.4 (2)
H1A—C1—H1C	109.5	C15—C16—H16	119.8
H1B—C1—H1C	109.5	C11—C16—H16	119.8
O1—C2—C1	107.8 (2)	N3—C17—C22	110.7 (2)
O1—C2—H2A	110.1	N3—C17—C18	110.7 (2)
C1—C2—H2A	110.1	C22—C17—C18	111.0 (2)
O1—C2—H2B	110.1	N3—C17—H17	108.1
C1—C2—H2B	110.1	C22—C17—H17	108.1
H2A—C2—H2B	108.5	C18—C17—H17	108.1
O2—C3—O1	123.8 (2)	C17—C18—C19	110.6 (3)
O2—C3—C4	124.9 (2)	C17—C18—H18A	109.5
O1—C3—C4	111.31 (19)	C19—C18—H18A	109.5
C5—C4—C7	106.1 (2)	C17—C18—H18B	109.5
C5—C4—C3	123.0 (2)	C19—C18—H18B	109.5
C7—C4—C3	130.9 (2)	H18A—C18—H18B	108.1
C4—C5—O3	110.5 (2)	C20—C19—C18	111.8 (3)
C4—C5—C6	134.8 (2)	C20—C19—H19A	109.2
O3—C5—C6	114.8 (2)	C18—C19—H19A	109.2
C5—C6—H6A	109.5	C20—C19—H19B	109.2
C5—C6—H6B	109.5	C18—C19—H19B	109.2
H6A—C6—H6B	109.5	H19A—C19—H19B	107.9
C5—C6—H6C	109.5	C17—C22—C21	111.6 (3)
H6A—C6—H6C	109.5	C17—C22—H22A	109.3
H6B—C6—H6C	109.5	C21—C22—H22A	109.3
C8—C7—C9	117.43 (19)	C17—C22—H22B	109.3
C8—C7—C4	105.55 (19)	C21—C22—H22B	109.3
C9—C7—C4	137.0 (2)	H22A—C22—H22B	108.0
N2—C8—C7	130.9 (2)	C20—C21—C22	111.9 (3)
N2—C8—O3	117.8 (2)	C20—C21—H21A	109.2
C7—C8—O3	111.33 (19)	C22—C21—H21A	109.2
O4—C9—C7	130.5 (2)	C20—C21—H21B	109.2
O4—C9—N1	118.1 (2)	C22—C21—H21B	109.2
C7—C9—N1	111.35 (19)	H21A—C21—H21B	107.9
N2—C10—N3	119.0 (2)	C10—N1—C11	119.56 (17)
N2—C10—N1	123.2 (2)	C10—N1—C9	124.19 (19)
N3—C10—N1	117.7 (2)	C11—N1—C9	116.10 (17)
C12—C11—C16	120.3 (2)	C10—N2—C8	112.82 (19)
C12—C11—N1	120.03 (19)	C10—N3—C17	122.8 (2)
C16—C11—N1	119.7 (2)	C10—N3—H3	114.2 (19)
C13—C12—C11	119.5 (2)	C17—N3—H3	118.7 (18)
C13—C12—H12	120.2	C3—O1—C2	118.03 (18)
C11—C12—H12	120.2	C8—O3—C5	106.58 (18)
C14—C13—C12	118.9 (2)	C21—C20—C19	111.4 (2)
C14—C13—H13	120.5	C21—C20—H20A	109.3
C12—C13—H13	120.5	C19—C20—H20A	109.3
F1—C14—C13	118.4 (2)	C21—C20—H20B	109.3
F1—C14—C15	118.5 (2)	C19—C20—H20B	109.3
C13—C14—C15	123.0 (2)	H20A—C20—H20B	108.0

O2—C3—C4—C5	1.6 (4)	N3—C17—C22—C21	179.1 (2)
O1—C3—C4—C5	−178.7 (2)	C18—C17—C22—C21	55.7 (4)
O2—C3—C4—C7	−179.5 (2)	C17—C22—C21—C20	−54.7 (4)
O1—C3—C4—C7	0.2 (3)	N2—C10—N1—C11	−172.6 (2)
C7—C4—C5—O3	−0.8 (3)	N3—C10—N1—C11	8.9 (3)
C3—C4—C5—O3	178.38 (19)	N2—C10—N1—C9	2.7 (4)
C7—C4—C5—C6	179.5 (3)	N3—C10—N1—C9	−175.9 (2)
C3—C4—C5—C6	−1.3 (4)	C12—C11—N1—C10	−107.4 (2)
C5—C4—C7—C8	0.7 (2)	C16—C11—N1—C10	72.2 (3)
C3—C4—C7—C8	−178.3 (2)	C12—C11—N1—C9	77.0 (3)
C5—C4—C7—C9	−179.3 (3)	C16—C11—N1—C9	−103.4 (2)
C3—C4—C7—C9	1.6 (4)	O4—C9—N1—C10	177.3 (2)
C9—C7—C8—N2	−0.6 (4)	C7—C9—N1—C10	−3.6 (3)
C4—C7—C8—N2	179.4 (2)	O4—C9—N1—C11	−7.3 (3)
C9—C7—C8—O3	179.58 (18)	C7—C9—N1—C11	171.78 (18)
C4—C7—C8—O3	−0.4 (2)	N3—C10—N2—C8	178.2 (2)
C8—C7—C9—O4	−178.6 (3)	N1—C10—N2—C8	−0.3 (3)
C4—C7—C9—O4	1.4 (5)	C7—C8—N2—C10	−0.7 (4)
C8—C7—C9—N1	2.5 (3)	O3—C8—N2—C10	179.16 (19)
C4—C7—C9—N1	−177.5 (2)	N2—C10—N3—C17	19.9 (4)
C16—C11—C12—C13	−0.2 (3)	N1—C10—N3—C17	−161.5 (2)
N1—C11—C12—C13	179.3 (2)	C22—C17—N3—C10	90.1 (3)
C11—C12—C13—C14	−0.1 (3)	C18—C17—N3—C10	−146.4 (3)
C12—C13—C14—F1	−179.7 (2)	O2—C3—O1—C2	4.3 (3)
C12—C13—C14—C15	0.2 (4)	C4—C3—O1—C2	−175.4 (2)
F1—C14—C15—C16	180.0 (2)	C1—C2—O1—C3	172.4 (2)
C13—C14—C15—C16	0.1 (4)	N2—C8—O3—C5	−179.9 (2)
C14—C15—C16—C11	−0.4 (4)	C7—C8—O3—C5	0.0 (2)
C12—C11—C16—C15	0.5 (3)	C4—C5—O3—C8	0.5 (3)
N1—C11—C16—C15	−179.1 (2)	C6—C5—O3—C8	−179.7 (2)
N3—C17—C18—C19	−179.1 (2)	C22—C21—C20—C19	53.8 (4)
C22—C17—C18—C19	−55.8 (4)	C18—C19—C20—C21	−54.4 (4)
C17—C18—C19—C20	55.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N2	0.98	2.41	2.813 (3)	104
C6—H6A···O2	0.96	2.45	3.039 (3)	120
C20—H20B···Cg3ⁱ	0.97	2.97	3.820 (4)	147
C14—F···Cg3ⁱⁱ	1.36 (1)	3.36 (1)	3.732 (3)	95
C3—O2···Cg2ⁱⁱⁱ	1.21 (1)	3.31 (1)	3.409 (3)	84

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₄FN₃O₄
M_r	413.44
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	9.2051 (8), 10.7957 (9), 11.6601 (10)
α, β, γ (°)	106.681 (1), 100.417 (2), 101.550 (2)
V (Å³)	1051.85 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.972, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	10785, 4505, 2941
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.182, 1.09
No. of reflections	4505
No. of parameters	276
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.21

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N2	0.98	2.41	2.813 (3)	103.9
C6—H6A···O2	0.96	2.45	3.039 (3)	119.7
C20—H20B···Cg3ⁱ	0.97	2.97	3.820 (4)	147
C14—F···Cg3ⁱⁱ	1.363 (3)	3.358 (2)	3.732 (3)	95
C3—O2···Cg2ⁱⁱⁱ	1.208 (3)	3.309 (2)	3.409 (3)	84

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

Acknowledgements

The authors gratefully acknowledge financial support of this work by the National Natural Science Foundation of China (project No. 20102001) and the Key Science Research Project of Hubei Provincial Department of Education (grant No. D200724001).

References

Bruker (2001). SMART (Version 5.628) and SAINT-Plus (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ding, M. W., Xu, S. Z. & Zhao, J. F. (2004). J. Org. Chem. 69, 8366–8371. Web of Science CrossRef PubMed CAS Google Scholar
Gangjee, A., Yang, J., McGuire, J. & Kisliuk, R. L. (2006). Bioorg. Med. Chem. 14, 8590–8598. Web of Science CrossRef PubMed CAS Google Scholar
Hu, Y.-G., Li, G.-H. & Zhou, M.-H. (2007). Acta Cryst. E63, o1836–o1838. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lagu, B., Tian, D., Chiu, G., Nagarathnam, D., Fang, J., Shen, Q., Forray, C., Ransom, R. W., Chang, R., Vyas, K., Zhang, K. & Gluchowski, C. (2000). Bioorg. Med. Chem. Lett. 10, 175–178. Web of Science CrossRef PubMed CAS Google Scholar
Miyazaki, Y., Tang, J., Maeda, Y., Nakano, M., Wang, L., Nolte, R. T., Sato, H., Sugai, M., Okamoto, Y., Truesdale, A. T., Daniel, F., Hassler, D. F., Nartey, E. N., Patrick, D. R., Hoc, M. L. & Ozawa, K. (2007). Bioorg. Med. Chem. Lett. 17, 1773–1778. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2001). SHELXTL. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2003). SADABS. Version 2.10. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Pages o311-o312

https://doi.org/10.1107/S1600536807066780

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Ethyl 3-(4-fluoro­phen­yl)-6-methyl-4-oxo-2-(1-cyclo­hexylamino)-3,4-di­hydro­furo[2,3-d]pyrimidine-5-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 3-(4-fluorophenyl)-6-methyl-4-oxo-2-(1-cyclohexylamino)-3,4-dihydrofuro[2,3-d]pyrimidine-5-carboxylate