(4-Fluoro­phen­yl)[6-(2-fur­yl)-7-nitro-2,3,4,6,7,8-hexa­hydro-1H-pyrido[1,2-a]pyrimidin-9-yl]methanone

Yaqub, M.; Shafiq, Z.; Qureshi, A.M.; Najam-ul-Haq, M.

doi:10.1107/S1600536809026373

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1869

doi:10.1107/S1600536809026373

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(4-Fluorophenyl)[6-(2-furyl)-7-nitro-2,3,4,6,7,8-hexahydro-1H-pyrido[1,2-a]pyrimidin-9-yl]methanone

Muhammad Yaqub,^a ^* Zahid Shafiq,^a Ashfaq M. Qureshi ^a and Muhammad Najam-ul-Haq ^a

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan
^*Correspondence e-mail: mayaqub2@yahoo.com

(Received 27 April 2009; accepted 7 July 2009; online 15 July 2009)

In the title compound, C₁₉H₁₈FN₃O₄, the fused pyridine and pyrimidine rings adopt half-chair conformations. The structure displays intramolecular N—H⋯O and intermolecular N—H⋯F hydrogen bonding.

Related literature

For the use of cyclic 1,1-enediamines in the synthesis of a wide variety of fused heterocycles, see: Huang & Wang, (1994 ); Yu et al. (2006 ); Yaqub et al. (2008 ). For related structures, see: Yu et al. (2007 ).

Experimental

Crystal data

C₁₉H₁₈FN₃O₄
M_r = 371.36
Orthorhombic, P n a 2₁
a = 15.375 (3) Å
b = 7.0706 (14) Å
c = 15.255 (3) Å
V = 1658.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 173 K
0.38 × 0.25 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.958, T_max = 0.979
3533 measured reflections
1943 independent reflections
1657 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.066
S = 1.01
1943 reflections
244 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4	0.88	1.86	2.579 (3)	138
N1—H1A⋯F1ⁱ	0.88	2.60	3.130 (3)	120
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Data collection: RAPID-AUTO (Rigaku, 2001 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809026373/pv2155sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026373/pv2155Isup2.hkl

checkCIF report

Comment top

Cyclic 1,1-enediamines known as heterocyclic ketene aminals (HKAs) have been exploited in different synthetic methodologies to build a wide variety of fused heterocycles (Huang & Wang, 1994; Yu, et al., 2006; Yaqub, et al., 2008). The title compound, (I), was prepared by treating nitro derivative of Baylis-Hillman acetates with heterocyclic ketene aminals. The structure of (I) is presented in this article.

The stucture of the title compound, (I), is shown in Fig. 1. The fused pyridyl (N2/C4—C8) and pyrimidyl (N1/N2/C1—C3/C8) rings adopt half-chair conformations, C5 and N2 atoms lie 0.596 (4) and 0.640 (5) Å, respectively, out of the planes formed by the remaining ring atoms. The structure displays an intramolecular (N—H···O) and an intermolecular (N—H···F) hydrogen bonding (details are in Table 1). The molecular dimensions in (I) are in accord with a the corrsponding dimensions reported for a structure very closely related to (I) (Yu, et al., 2007).

Related literature top

For the use of cyclic 1,1-enediamines in the synthesis of a wide variety of fused heterocycles, see: Huang & Wang, (1994); Yu et al. (2006); Yaqub et al. (2008). For related structures, see: Yu et al. (2007).

Experimental top

(E)-2-Nitro-3-(2-furanyl)allyl acetate 2 (0.15 g, 0.71 mmol) and ketene aminal 2 (0.146 g, 0.71 mmol) were stirred in 20 ml of dichloromethane (DCM) at 273 K for one hour. Temperature was allowed to rise up to room temperature and stirring was further continued for 6 hrs. Solvent was evaporated and residue was passed through the column. The elution was carried out by petroleum ether: ethyl acetate (3:1) to get the title compound as a light yellow solid. The single crystals of (I) were grown in dichloromethane - petroleum ether (1:5) system at room temperature by slow evaporation. Yield: 62% (0.16 g), m.p. 417–418 K (lit. m.p. 418–419 K).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at 50% probability level.
	Fig. 2. The formation of the title compound.

(4-Fluorophenyl)[6-(2-furyl)-7-nitro-2,3,4,6,7,8-hexahydro-1H- pyrido[1,2-a]pyrimidin-9-yl]methanone top

Crystal data top

C₁₉H₁₈FN₃O₄	F(000) = 776
M_r = 371.36	D_x = 1.487 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3533 reflections
a = 15.375 (3) Å	θ = 2.7–27.4°
b = 7.0706 (14) Å	µ = 0.11 mm⁻¹
c = 15.255 (3) Å	T = 173 K
V = 1658.3 (6) Å³	Plate, yellow
Z = 4	0.38 × 0.25 × 0.19 mm

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	1943 independent reflections
Radiation source: rotating anode	1657 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans at fixed χ = 45°	θ_max = 27.4°, θ_min = 2.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −19→19
T_min = 0.958, T_max = 0.979	k = −9→9
3533 measured reflections	l = −19→19

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0225P)²] where P = (F_o² + 2F_c²)/3
1943 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₉H₁₈FN₃O₄	V = 1658.3 (6) Å³
M_r = 371.36	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 15.375 (3) Å	µ = 0.11 mm⁻¹
b = 7.0706 (14) Å	T = 173 K
c = 15.255 (3) Å	0.38 × 0.25 × 0.19 mm

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	1943 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1657 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.979	R_int = 0.020
3533 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.066	H-atom parameters constrained
S = 1.01	Δρ_max = 0.19 e Å⁻³
1943 reflections	Δρ_min = −0.21 e Å⁻³
244 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.

Flack parameter cannot be determined correctly because the crystal consists of light atoms only, and because the radiation is MoKα. In the final stage of structure refinement with SHELXL, MERG 3 card was used, i.e. Friedel pairs (1590) were merged

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	−0.27105 (10)	0.6451 (2)	0.11441 (12)	0.0346 (4)
O1	−0.16942 (12)	−0.3771 (3)	0.52236 (12)	0.0270 (5)
O2	0.06546 (13)	0.0877 (3)	0.48554 (15)	0.0412 (6)
O3	−0.04035 (13)	0.2693 (3)	0.52399 (15)	0.0336 (5)
O4	0.03402 (12)	0.0794 (3)	0.16274 (12)	0.0249 (4)
N1	0.08544 (14)	−0.2010 (3)	0.25757 (16)	0.0216 (5)
H1A	0.0896	−0.1296	0.2105	0.026*
N2	0.01886 (14)	−0.2546 (3)	0.39083 (16)	0.0188 (5)
N3	−0.01178 (15)	0.1242 (3)	0.49235 (15)	0.0225 (5)
C1	0.14602 (18)	−0.3583 (4)	0.2649 (2)	0.0249 (6)
H1B	0.2037	−0.3107	0.2836	0.030*
H1C	0.1528	−0.4201	0.2071	0.030*
C2	0.1128 (2)	−0.5011 (4)	0.3313 (2)	0.0263 (7)
H2A	0.0632	−0.5723	0.3062	0.032*
H2B	0.1595	−0.5923	0.3459	0.032*
C3	0.08430 (18)	−0.3984 (4)	0.41276 (18)	0.0223 (6)
H3A	0.0594	−0.4898	0.4551	0.027*
H3B	0.1352	−0.3371	0.4406	0.027*
C4	−0.04462 (16)	−0.2163 (3)	0.45963 (18)	0.0174 (6)
H4A	−0.0171	−0.2410	0.5179	0.021*
C5	−0.07782 (16)	−0.0134 (3)	0.45763 (17)	0.0163 (5)
H5A	−0.1308	−0.0059	0.4956	0.020*
C6	−0.10374 (16)	0.0431 (3)	0.36448 (17)	0.0172 (6)
H6A	−0.1581	−0.0235	0.3484	0.021*
H6B	−0.1156	0.1806	0.3630	0.021*
C7	−0.03447 (17)	−0.0028 (4)	0.29753 (17)	0.0177 (5)
C8	0.02392 (17)	−0.1551 (3)	0.31586 (17)	0.0162 (5)
C9	−0.12129 (16)	−0.3457 (3)	0.44889 (18)	0.0180 (5)
C10	−0.24018 (19)	−0.4814 (4)	0.4965 (2)	0.0303 (7)
H10A	−0.2853	−0.5234	0.5342	0.036*
C11	−0.23634 (19)	−0.5153 (4)	0.4105 (2)	0.0270 (7)
H11A	−0.2773	−0.5845	0.3768	0.032*
C12	−0.15887 (17)	−0.4277 (4)	0.37916 (19)	0.0235 (6)
H12A	−0.1380	−0.4273	0.3205	0.028*
C13	−0.02627 (17)	0.0996 (3)	0.21865 (17)	0.0173 (6)
C14	−0.09337 (16)	0.2471 (3)	0.19533 (18)	0.0170 (6)
C15	−0.18225 (17)	0.2120 (3)	0.20063 (19)	0.0208 (6)
H15A	−0.2018	0.0944	0.2234	0.025*
C16	−0.24299 (18)	0.3450 (4)	0.17349 (19)	0.0240 (6)
H16A	−0.3036	0.3198	0.1763	0.029*
C17	−0.21204 (18)	0.5148 (4)	0.14232 (19)	0.0232 (6)
C18	−0.12529 (18)	0.5575 (4)	0.13609 (18)	0.0236 (6)
H18A	−0.1065	0.6767	0.1145	0.028*
C19	−0.06578 (18)	0.4215 (4)	0.16217 (18)	0.0212 (6)
H19A	−0.0053	0.4472	0.1575	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0346 (10)	0.0353 (9)	0.0338 (10)	0.0157 (8)	−0.0003 (9)	0.0075 (8)
O1	0.0294 (11)	0.0320 (11)	0.0195 (11)	−0.0085 (9)	0.0055 (9)	−0.0003 (9)
O2	0.0187 (11)	0.0488 (14)	0.0560 (16)	−0.0057 (10)	0.0028 (11)	−0.0223 (12)
O3	0.0376 (12)	0.0181 (10)	0.0451 (15)	0.0001 (9)	−0.0059 (11)	−0.0077 (9)
O4	0.0243 (11)	0.0305 (10)	0.0200 (10)	0.0058 (9)	0.0057 (9)	0.0059 (9)
N1	0.0236 (13)	0.0221 (11)	0.0193 (12)	0.0065 (10)	0.0051 (10)	0.0054 (10)
N2	0.0193 (11)	0.0184 (10)	0.0187 (11)	0.0032 (10)	0.0001 (10)	0.0020 (9)
N3	0.0262 (14)	0.0234 (12)	0.0178 (12)	−0.0046 (11)	−0.0004 (10)	0.0000 (10)
C1	0.0230 (14)	0.0254 (14)	0.0263 (15)	0.0098 (13)	0.0049 (13)	−0.0002 (13)
C2	0.0310 (16)	0.0190 (12)	0.0291 (16)	0.0051 (13)	0.0006 (13)	0.0019 (12)
C3	0.0240 (15)	0.0207 (13)	0.0222 (15)	0.0033 (12)	0.0003 (12)	0.0072 (12)
C4	0.0191 (13)	0.0214 (13)	0.0117 (13)	−0.0014 (11)	0.0027 (12)	0.0033 (11)
C5	0.0142 (12)	0.0178 (12)	0.0169 (13)	−0.0022 (11)	0.0006 (11)	−0.0018 (11)
C6	0.0161 (13)	0.0148 (12)	0.0206 (15)	0.0013 (11)	0.0015 (12)	0.0011 (11)
C7	0.0198 (13)	0.0157 (12)	0.0176 (14)	−0.0006 (12)	0.0006 (11)	−0.0014 (10)
C8	0.0154 (13)	0.0165 (12)	0.0167 (13)	−0.0046 (11)	−0.0003 (11)	−0.0011 (11)
C9	0.0216 (13)	0.0151 (12)	0.0173 (13)	0.0035 (11)	0.0029 (12)	0.0015 (11)
C10	0.0283 (17)	0.0289 (15)	0.0338 (19)	−0.0100 (14)	0.0062 (14)	0.0011 (14)
C11	0.0261 (17)	0.0195 (13)	0.0354 (19)	−0.0037 (13)	−0.0020 (14)	−0.0056 (13)
C12	0.0261 (16)	0.0231 (13)	0.0212 (15)	0.0003 (12)	0.0005 (13)	−0.0023 (12)
C13	0.0184 (13)	0.0179 (13)	0.0154 (13)	−0.0012 (11)	−0.0012 (11)	−0.0020 (11)
C14	0.0213 (14)	0.0180 (11)	0.0119 (12)	0.0010 (12)	0.0004 (11)	−0.0020 (10)
C15	0.0242 (14)	0.0189 (13)	0.0194 (14)	−0.0026 (12)	−0.0022 (13)	0.0008 (12)
C16	0.0202 (14)	0.0304 (14)	0.0214 (16)	0.0007 (13)	−0.0016 (12)	−0.0026 (12)
C17	0.0300 (16)	0.0249 (13)	0.0147 (13)	0.0126 (12)	0.0002 (12)	0.0014 (11)
C18	0.0322 (16)	0.0200 (13)	0.0185 (15)	0.0025 (12)	0.0049 (12)	0.0047 (12)
C19	0.0233 (15)	0.0231 (13)	0.0171 (14)	−0.0001 (12)	0.0035 (12)	−0.0002 (12)

Geometric parameters (Å, º) top

F1—C17	1.361 (3)	C5—C6	1.529 (4)
O1—C9	1.361 (3)	C5—H5A	1.0000
O1—C10	1.372 (3)	C6—C7	1.511 (3)
O2—N3	1.220 (3)	C6—H6A	0.9900
O3—N3	1.216 (3)	C6—H6B	0.9900
O4—C13	1.268 (3)	C7—C13	1.410 (4)
N1—C8	1.338 (3)	C7—C8	1.430 (3)
N1—C1	1.455 (3)	C9—C12	1.342 (4)
N1—H1A	0.8800	C10—C11	1.334 (4)
N2—C8	1.345 (3)	C10—H10A	0.9500
N2—C4	1.458 (3)	C11—C12	1.425 (4)
N2—C3	1.469 (3)	C11—H11A	0.9500
N3—C5	1.503 (3)	C12—H12A	0.9500
C1—C2	1.518 (4)	C13—C14	1.509 (4)
C1—H1B	0.9900	C14—C15	1.391 (3)
C1—H1C	0.9900	C14—C19	1.399 (3)
C2—C3	1.505 (4)	C15—C16	1.389 (4)
C2—H2A	0.9900	C15—H15A	0.9500
C2—H2B	0.9900	C16—C17	1.376 (4)
C3—H3A	0.9900	C16—H16A	0.9500
C3—H3B	0.9900	C17—C18	1.371 (4)
C4—C9	1.501 (3)	C18—C19	1.385 (4)
C4—C5	1.523 (3)	C18—H18A	0.9500
C4—H4A	1.0000	C19—H19A	0.9500

C9—O1—C10	106.4 (2)	C7—C6—H6B	109.0
C8—N1—C1	125.9 (2)	C5—C6—H6B	109.0
C8—N1—H1A	117.0	H6A—C6—H6B	107.8
C1—N1—H1A	117.0	C13—C7—C8	119.8 (2)
C8—N2—C4	123.6 (2)	C13—C7—C6	122.0 (2)
C8—N2—C3	121.1 (2)	C8—C7—C6	118.2 (2)
C4—N2—C3	115.0 (2)	N1—C8—N2	118.6 (2)
O3—N3—O2	124.4 (2)	N1—C8—C7	119.8 (2)
O3—N3—C5	116.2 (2)	N2—C8—C7	121.6 (2)
O2—N3—C5	119.4 (2)	C12—C9—O1	110.4 (2)
N1—C1—C2	110.2 (2)	C12—C9—C4	133.5 (3)
N1—C1—H1B	109.6	O1—C9—C4	115.9 (2)
C2—C1—H1B	109.6	C11—C10—O1	110.1 (3)
N1—C1—H1C	109.6	C11—C10—H10A	124.9
C2—C1—H1C	109.6	O1—C10—H10A	124.9
H1B—C1—H1C	108.1	C10—C11—C12	106.8 (3)
C3—C2—C1	109.1 (2)	C10—C11—H11A	126.6
C3—C2—H2A	109.9	C12—C11—H11A	126.6
C1—C2—H2A	109.9	C9—C12—C11	106.3 (3)
C3—C2—H2B	109.9	C9—C12—H12A	126.8
C1—C2—H2B	109.9	C11—C12—H12A	126.8
H2A—C2—H2B	108.3	O4—C13—C7	125.6 (2)
N2—C3—C2	110.2 (2)	O4—C13—C14	114.8 (2)
N2—C3—H3A	109.6	C7—C13—C14	119.7 (2)
C2—C3—H3A	109.6	C15—C14—C19	118.4 (2)
N2—C3—H3B	109.6	C15—C14—C13	122.3 (2)
C2—C3—H3B	109.6	C19—C14—C13	119.1 (2)
H3A—C3—H3B	108.1	C16—C15—C14	121.5 (2)
N2—C4—C9	109.5 (2)	C16—C15—H15A	119.2
N2—C4—C5	112.6 (2)	C14—C15—H15A	119.2
C9—C4—C5	108.0 (2)	C17—C16—C15	117.5 (3)
N2—C4—H4A	108.9	C17—C16—H16A	121.3
C9—C4—H4A	108.9	C15—C16—H16A	121.3
C5—C4—H4A	108.9	F1—C17—C18	118.6 (2)
N3—C5—C4	112.1 (2)	F1—C17—C16	117.9 (2)
N3—C5—C6	109.5 (2)	C18—C17—C16	123.5 (3)
C4—C5—C6	110.6 (2)	C17—C18—C19	118.0 (2)
N3—C5—H5A	108.2	C17—C18—H18A	121.0
C4—C5—H5A	108.2	C19—C18—H18A	121.0
C6—C5—H5A	108.2	C18—C19—C14	121.0 (2)
C7—C6—C5	112.9 (2)	C18—C19—H19A	119.5
C7—C6—H6A	109.0	C14—C19—H19A	119.5
C5—C6—H6A	109.0

C8—N1—C1—C2	18.4 (4)	C6—C7—C8—N2	−0.8 (4)
N1—C1—C2—C3	−47.0 (3)	C10—O1—C9—C12	−0.6 (3)
C8—N2—C3—C2	−36.6 (3)	C10—O1—C9—C4	173.9 (2)
C4—N2—C3—C2	149.5 (2)	N2—C4—C9—C12	−30.1 (4)
C1—C2—C3—N2	56.1 (3)	C5—C4—C9—C12	92.8 (3)
C8—N2—C4—C9	96.3 (3)	N2—C4—C9—O1	156.9 (2)
C3—N2—C4—C9	−90.0 (3)	C5—C4—C9—O1	−80.1 (3)
C8—N2—C4—C5	−23.8 (3)	C9—O1—C10—C11	0.5 (3)
C3—N2—C4—C5	149.9 (2)	O1—C10—C11—C12	−0.1 (3)
O3—N3—C5—C4	−153.2 (2)	O1—C9—C12—C11	0.5 (3)
O2—N3—C5—C4	28.6 (3)	C4—C9—C12—C11	−172.7 (3)
O3—N3—C5—C6	83.7 (3)	C10—C11—C12—C9	−0.3 (3)
O2—N3—C5—C6	−94.6 (3)	C8—C7—C13—O4	−5.9 (4)
N2—C4—C5—N3	−74.9 (3)	C6—C7—C13—O4	174.2 (2)
C9—C4—C5—N3	164.1 (2)	C8—C7—C13—C14	173.9 (2)
N2—C4—C5—C6	47.7 (3)	C6—C7—C13—C14	−6.1 (4)
C9—C4—C5—C6	−73.3 (3)	O4—C13—C14—C15	132.0 (3)
N3—C5—C6—C7	74.7 (2)	C7—C13—C14—C15	−47.8 (4)
C4—C5—C6—C7	−49.4 (3)	O4—C13—C14—C19	−44.1 (3)
C5—C6—C7—C13	−153.3 (2)	C7—C13—C14—C19	136.1 (3)
C5—C6—C7—C8	26.7 (3)	C19—C14—C15—C16	0.4 (4)
C1—N1—C8—N2	3.7 (4)	C13—C14—C15—C16	−175.7 (3)
C1—N1—C8—C7	−176.4 (2)	C14—C15—C16—C17	−1.0 (4)
C4—N2—C8—N1	179.2 (2)	C15—C16—C17—F1	179.1 (2)
C3—N2—C8—N1	5.9 (4)	C15—C16—C17—C18	0.7 (4)
C4—N2—C8—C7	−0.7 (4)	F1—C17—C18—C19	−178.0 (2)
C3—N2—C8—C7	−174.0 (2)	C16—C17—C18—C19	0.4 (4)
C13—C7—C8—N1	−0.7 (4)	C17—C18—C19—C14	−1.1 (4)
C6—C7—C8—N1	179.2 (2)	C15—C14—C19—C18	0.7 (4)
C13—C7—C8—N2	179.2 (2)	C13—C14—C19—C18	176.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4	0.88	1.86	2.579 (3)	138
N1—H1A···F1ⁱ	0.88	2.60	3.130 (3)	120

Symmetry code: (i) x+1/2, −y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈FN₃O₄
M_r	371.36
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	15.375 (3), 7.0706 (14), 15.255 (3)
V (Å³)	1658.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.38 × 0.25 × 0.19

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.958, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	3533, 1943, 1657
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.066, 1.01
No. of reflections	1943
No. of parameters	244
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.21

Computer programs: RAPID-AUTO (Rigaku, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4	0.88	1.86	2.579 (3)	138
N1—H1A···F1ⁱ	0.88	2.60	3.130 (3)	120

Symmetry code: (i) x+1/2, −y+1/2, z.

Acknowledgements

The Institute of Chemistry, Chinese Academy of Science, Beijing, is thanked for providing the single-crystal facility and the Higher Education Commission, Islamabad, Pakistan, is gratefully acknowledged for providing financial support.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Huang, Z.-T. & Wang, M.-X. (1994). Heterocycles, 37, 1233–1262. CrossRef CAS Google Scholar
Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yaqub, M., Yu, C.-Y., Jia, Y.-M. & Huang, Z.-T. (2008). Synlett, pp. 1357–1360. Google Scholar
Yu, C.-Y., Yang, P.-H., Zhao, M.-X. & Huang, Z.-T. (2006). Synlett. pp. 1835–1840. Web of Science CrossRef Google Scholar
Yu, C.-Y., Yuan, X.-N. & Huang, Z.-T. (2007). Acta Cryst. E63, o3186. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 8| August 2009| Page o1869

doi:10.1107/S1600536809026373

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

(4-Fluoro­phen­yl)[6-(2-fur­yl)-7-nitro-2,3,4,6,7,8-hexa­hydro-1H-pyrido[1,2-a]pyrimidin-9-yl]methanone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(4-Fluorophenyl)[6-(2-furyl)-7-nitro-2,3,4,6,7,8-hexahydro-1H-pyrido[1,2-a]pyrimidin-9-yl]methanone