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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
aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan
*Correspondence e-mail: mayaqub2@yahoo.com
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
|
Refinement
|
|
Data collection: RAPID-AUTO (Rigaku, 2001); cell 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
10.1107/S1600536809026373/pv2155sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809026373/pv2155Isup2.hkl
(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).
An
could not be established by effects because the crystal consists of light atoms only. Therefore, Friedel pairs (1590) were merged. All H atoms were positioned geometrically, with N—H = 0.88 and C—H = 0.95, 0.99 and 1.00 Å, for aromatic, methylene and methine H-atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C, N).Data collection: RAPID-AUTO (Rigaku, 2001); cell
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). ![]() | Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at 50% probability level. |
![]() | Fig. 2. The formation of the title compound. |
C19H18FN3O4 | F(000) = 776 |
Mr = 371.36 | Dx = 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 |
Rigaku R-AXIS RAPID IP area-detector diffractometer | 1943 independent reflections |
Radiation source: rotating anode | 1657 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω scans at fixed χ = 45° | θmax = 27.4°, θmin = 2.7° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −19→19 |
Tmin = 0.958, Tmax = 0.979 | k = −9→9 |
3533 measured reflections | l = −19→19 |
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(Fo2) + (0.0225P)2] where P = (Fo2 + 2Fc2)/3 |
1943 reflections | (Δ/σ)max < 0.001 |
244 parameters | Δρmax = 0.19 e Å−3 |
1 restraint | Δρmin = −0.21 e Å−3 |
C19H18FN3O4 | V = 1658.3 (6) Å3 |
Mr = 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 |
Rigaku R-AXIS RAPID IP area-detector diffractometer | 1943 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1657 reflections with I > 2σ(I) |
Tmin = 0.958, Tmax = 0.979 | Rint = 0.020 |
3533 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 1 restraint |
wR(F2) = 0.066 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.19 e Å−3 |
1943 reflections | Δρmin = −0.21 e Å−3 |
244 parameters |
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 |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.958, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3533, 1943, 1657 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.19, −0.21 |
Computer programs: RAPID-AUTO (Rigaku, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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
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.
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).