Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045643/hk2326sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045643/hk2326Isup2.hkl |
CCDC reference: 664211
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.064
- wR factor = 0.191
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT707_ALERT_1_A D...A Calc 26.051(13), Rep 3.2625(3), Dev.. 1752.96 Sigma C22 -O1 1.555 6.545 PLAT726_ALERT_1_A H...A Calc 25.59000, Rep 2.35000 Dev... 23.24 Ang. H22 -O1 1.555 6.545 PLAT728_ALERT_1_A D-H..A Calc 119.00, Rep 168.00 Dev... 49.00 Deg. C22 -H22 -O1 1.555 1.555 6.545 PLAT737_ALERT_1_A D...A Calc 2.863(5), Rep 2.8628(3) ...... 9.90 su-Ra N2 -O2 1.555 2.555 PLAT737_ALERT_1_A D...A Calc 26.051(13), Rep 3.2625(3) ...... 9.90 su-Ra C22 -O1 1.555 6.545
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 39 Perc.
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.115 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N4 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C17 ... 1.43 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C3 = ... S
5 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound, (I), was prepared by the reaction of 4-fluorobenzaldehyde (124 mg, 1 mmol), 2-(5,5-dimethyl-3-oxocyclohex-1-enylamino)benzoic acid (259 mg, 1 mmol) with malononitrile (66 mg, 1 mmol) in solvent of ethylene glycol (2.0 ml) at 393 K under microwave irradiation (maximum power 200 W, initial power 100 W) for 5 min (yield; 339 mg, 82%, m.p. 534–535 K). Single crystals suitable for X-ray analysis were obtained from an ethanol solution (95%) by slow evaporation.
H atoms were positioned geometrically, with N—H = 0.86 Å (for NH) and C—H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.
The pyrido[1,2-a]pyrimidine core has been a successful motif for the development of biologically interesting molecules. Compounds containing the pyrido[1,2-a]pyrimidine ring system have been used as analgesics (Hermecz & Meszaros, 1988), antiallergics (Doria et al., 1983), antiasthmatics, antipsychotics (Colpaert, 2003), gastrointestinal protective (Knoll et al., 1987), neurotropic and stress-protecting agents (Kozlovskaya et al., 1995). Moreover, some examples are key intermediates for the synthesis of rutaecarpine alkaloids and several are neutral hydrogen chloride acceptors in organic synthesis (Hermecz et al., 1996, and references therein). The discovery of quinolino[1,2-a]quinazoline including imidazo[1,2-a]pyridine moiety as new potential pharmacological molecules may be of great significance. We report herein the crystal structure of the title compound, (I).
In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987). It contains one C25H20FN3O2 molecule and one C3H7NO molecule.
Rings A (N1/C1—C4/C9), B (C4—C9) and C (N1/N2/C1/C10—C12) are not planar, having total puckering amplitudes, QT, of 0.467 (2), 0.504 (3) and 0.193 (2) Å, respectively [φ = 158.80 (7)°, θ = 154.08 (5)°; φ = 3.15 (5)°, θ = 122.37 (5)° and φ = 157.13 (17)°, θ = 79.02 (16)°, respectively] (Cremer & Pople, 1975). Rings A and C have boat conformations, while ring B adopts an envelope conformation with atom C7 displaced by 0.698 (3) Å from the plane of the other ring atoms. Rings D (C11—C16) and E (C18—C23) are, of course, planar and they are oriented at a dihedral angle of 74.86 (2)°.
In the crystal structure, intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they seem to be effective in the stabilization of the structure.
For related literature, see: Hermecz & Meszaros (1988); Doria et al. (1983); Colpaert (2003); Knoll et al. (1987); Kozlovskaya et al. (1995); Hermecz et al. (1996, and references therein). For general background, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999).
C25H20FN3O2·C3H7NO | F(000) = 2048 |
Mr = 486.54 | Dx = 1.332 Mg m−3 |
Monoclinic, C2/c | Melting point = 534–535 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 36.140 (15) Å | Cell parameters from 1017 reflections |
b = 11.701 (5) Å | θ = 2.5–19.7° |
c = 11.780 (5) Å | µ = 0.09 mm−1 |
β = 103.122 (6)° | T = 298 K |
V = 4851 (4) Å3 | Block, colorless |
Z = 8 | 0.26 × 0.13 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 4262 independent reflections |
Radiation source: fine-focus sealed tube | 1649 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.115 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −42→42 |
Tmin = 0.976, Tmax = 0.991 | k = −8→13 |
12335 measured reflections | l = −14→13 |
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) = 0.191 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0618P)2] where P = (Fo2 + 2Fc2)/3 |
4262 reflections | (Δ/σ)max < 0.001 |
325 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C25H20FN3O2·C3H7NO | V = 4851 (4) Å3 |
Mr = 486.54 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 36.140 (15) Å | µ = 0.09 mm−1 |
b = 11.701 (5) Å | T = 298 K |
c = 11.780 (5) Å | 0.26 × 0.13 × 0.10 mm |
β = 103.122 (6)° |
Bruker SMART CCD area-detector diffractometer | 4262 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1649 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.991 | Rint = 0.115 |
12335 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.191 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.28 e Å−3 |
4262 reflections | Δρmin = −0.26 e Å−3 |
325 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. |
x | y | z | Uiso*/Ueq | ||
F1 | 0.22422 (9) | 0.2184 (3) | 0.3860 (3) | 0.0876 (12) | |
N1 | 0.11112 (9) | 0.6953 (3) | 0.4752 (3) | 0.0286 (9) | |
N2 | 0.05613 (10) | 0.6431 (3) | 0.3357 (3) | 0.0343 (10) | |
H2 | 0.0453 | 0.6303 | 0.2639 | 0.041* | |
N3 | 0.09081 (13) | 0.6056 (4) | 0.0661 (4) | 0.0578 (13) | |
N4 | 0.04876 (14) | 0.9481 (5) | 0.0533 (5) | 0.0693 (15) | |
O1 | 0.22506 (9) | 0.7939 (3) | 0.3657 (3) | 0.0506 (10) | |
O2 | −0.00121 (9) | 0.6344 (3) | 0.3816 (3) | 0.0513 (10) | |
O3 | 0.04920 (14) | 1.0979 (4) | −0.0674 (4) | 0.0983 (17) | |
C1 | 0.09488 (12) | 0.6598 (4) | 0.3608 (4) | 0.0291 (11) | |
C2 | 0.11659 (12) | 0.6478 (4) | 0.2838 (3) | 0.0284 (11) | |
C3 | 0.15981 (12) | 0.6583 (4) | 0.3207 (4) | 0.0338 (12) | |
H3 | 0.1682 | 0.6927 | 0.2550 | 0.041* | |
C4 | 0.16847 (12) | 0.7426 (4) | 0.4186 (4) | 0.0300 (11) | |
C5 | 0.20306 (13) | 0.8133 (4) | 0.4277 (4) | 0.0371 (12) | |
C6 | 0.20967 (13) | 0.9095 (4) | 0.5141 (4) | 0.0442 (14) | |
H6A | 0.2222 | 0.9716 | 0.4831 | 0.053* | |
H6B | 0.2267 | 0.8834 | 0.5854 | 0.053* | |
C7 | 0.17301 (13) | 0.9552 (4) | 0.5435 (4) | 0.0391 (13) | |
C8 | 0.15274 (13) | 0.8525 (4) | 0.5815 (4) | 0.0380 (12) | |
H8A | 0.1680 | 0.8226 | 0.6539 | 0.046* | |
H8B | 0.1286 | 0.8772 | 0.5960 | 0.046* | |
C9 | 0.14575 (12) | 0.7590 (4) | 0.4918 (4) | 0.0284 (11) | |
C10 | 0.03298 (13) | 0.6450 (4) | 0.4133 (4) | 0.0352 (12) | |
C11 | 0.05287 (12) | 0.6541 (4) | 0.5351 (4) | 0.0306 (11) | |
C12 | 0.09173 (12) | 0.6765 (4) | 0.5647 (4) | 0.0284 (11) | |
C13 | 0.11082 (13) | 0.6742 (4) | 0.6823 (4) | 0.0382 (13) | |
H13 | 0.1370 | 0.6849 | 0.7035 | 0.046* | |
C14 | 0.09043 (14) | 0.6560 (4) | 0.7664 (4) | 0.0454 (14) | |
H14 | 0.1029 | 0.6564 | 0.8447 | 0.055* | |
C15 | 0.05194 (14) | 0.6373 (4) | 0.7363 (4) | 0.0488 (14) | |
H15 | 0.0385 | 0.6268 | 0.7941 | 0.059* | |
C16 | 0.03329 (13) | 0.6341 (4) | 0.6207 (4) | 0.0424 (13) | |
H16 | 0.0074 | 0.6184 | 0.6003 | 0.051* | |
C17 | 0.10108 (13) | 0.6233 (4) | 0.1636 (4) | 0.0351 (12) | |
C18 | 0.17897 (12) | 0.5425 (4) | 0.3426 (4) | 0.0352 (12) | |
C19 | 0.17453 (14) | 0.4746 (4) | 0.4351 (4) | 0.0460 (14) | |
H19 | 0.1610 | 0.5025 | 0.4875 | 0.055* | |
C20 | 0.18988 (15) | 0.3666 (5) | 0.4502 (5) | 0.0580 (16) | |
H20 | 0.1865 | 0.3211 | 0.5118 | 0.070* | |
C21 | 0.20995 (15) | 0.3276 (5) | 0.3744 (5) | 0.0522 (15) | |
C22 | 0.21558 (13) | 0.3911 (5) | 0.2825 (5) | 0.0525 (16) | |
H22 | 0.2293 | 0.3625 | 0.2310 | 0.063* | |
C23 | 0.20018 (13) | 0.4988 (5) | 0.2691 (4) | 0.0433 (14) | |
H23 | 0.2042 | 0.5440 | 0.2081 | 0.052* | |
C24 | 0.18274 (15) | 1.0405 (5) | 0.6442 (5) | 0.0620 (17) | |
H24A | 0.1956 | 1.1052 | 0.6208 | 0.093* | |
H24B | 0.1990 | 1.0045 | 0.7104 | 0.093* | |
H24C | 0.1598 | 1.0655 | 0.6646 | 0.093* | |
C25 | 0.14790 (15) | 1.0147 (4) | 0.4378 (5) | 0.0600 (16) | |
H25A | 0.1614 | 1.0783 | 0.4152 | 0.090* | |
H25B | 0.1251 | 1.0416 | 0.4578 | 0.090* | |
H25C | 0.1415 | 0.9616 | 0.3743 | 0.090* | |
C26 | 0.05002 (18) | 1.0573 (6) | 0.0287 (7) | 0.079 (2) | |
H26 | 0.0517 | 1.1085 | 0.0900 | 0.095* | |
C27 | 0.0441 (2) | 0.8640 (6) | −0.0401 (6) | 0.105 (3) | |
H27A | 0.0433 | 0.7888 | −0.0082 | 0.158* | |
H27B | 0.0650 | 0.8694 | −0.0775 | 0.158* | |
H27C | 0.0207 | 0.8785 | −0.0961 | 0.158* | |
C28 | 0.0502 (2) | 0.9086 (7) | 0.1701 (6) | 0.120 (3) | |
H28A | 0.0484 | 0.8268 | 0.1701 | 0.181* | |
H28B | 0.0295 | 0.9410 | 0.1976 | 0.181* | |
H28C | 0.0738 | 0.9317 | 0.2203 | 0.181* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.081 (3) | 0.059 (2) | 0.112 (3) | 0.032 (2) | −0.003 (2) | −0.017 (2) |
N1 | 0.026 (2) | 0.035 (2) | 0.025 (2) | −0.0005 (19) | 0.0064 (17) | −0.0030 (18) |
N2 | 0.029 (2) | 0.043 (3) | 0.028 (2) | −0.003 (2) | −0.0001 (18) | −0.0034 (19) |
N3 | 0.070 (3) | 0.062 (3) | 0.038 (3) | 0.002 (3) | 0.006 (2) | 0.000 (3) |
N4 | 0.081 (4) | 0.047 (3) | 0.079 (4) | −0.003 (3) | 0.015 (3) | 0.006 (3) |
O1 | 0.039 (2) | 0.061 (3) | 0.058 (2) | −0.0024 (19) | 0.0240 (18) | 0.0025 (19) |
O2 | 0.027 (2) | 0.075 (3) | 0.049 (2) | −0.0054 (19) | 0.0022 (16) | 0.0020 (19) |
O3 | 0.143 (5) | 0.073 (3) | 0.082 (3) | −0.013 (3) | 0.032 (3) | 0.011 (3) |
C1 | 0.026 (3) | 0.031 (3) | 0.027 (3) | −0.002 (2) | −0.001 (2) | −0.001 (2) |
C2 | 0.031 (3) | 0.031 (3) | 0.023 (3) | 0.003 (2) | 0.005 (2) | −0.001 (2) |
C3 | 0.035 (3) | 0.038 (3) | 0.032 (3) | 0.000 (2) | 0.016 (2) | 0.002 (2) |
C4 | 0.025 (3) | 0.034 (3) | 0.031 (3) | −0.001 (2) | 0.008 (2) | 0.001 (2) |
C5 | 0.028 (3) | 0.042 (3) | 0.040 (3) | 0.004 (3) | 0.004 (2) | 0.006 (3) |
C6 | 0.033 (3) | 0.047 (4) | 0.052 (3) | −0.007 (3) | 0.007 (2) | 0.005 (3) |
C7 | 0.038 (3) | 0.036 (3) | 0.043 (3) | −0.007 (3) | 0.010 (2) | −0.004 (3) |
C8 | 0.032 (3) | 0.045 (3) | 0.037 (3) | −0.003 (3) | 0.010 (2) | −0.006 (3) |
C9 | 0.025 (3) | 0.029 (3) | 0.030 (3) | 0.002 (2) | 0.004 (2) | 0.003 (2) |
C10 | 0.027 (3) | 0.036 (3) | 0.042 (3) | −0.004 (2) | 0.006 (2) | 0.002 (2) |
C11 | 0.028 (3) | 0.032 (3) | 0.035 (3) | 0.001 (2) | 0.012 (2) | 0.003 (2) |
C12 | 0.030 (3) | 0.026 (3) | 0.032 (3) | 0.003 (2) | 0.010 (2) | −0.001 (2) |
C13 | 0.030 (3) | 0.046 (3) | 0.036 (3) | −0.004 (2) | 0.003 (2) | 0.003 (3) |
C14 | 0.048 (3) | 0.057 (4) | 0.031 (3) | 0.001 (3) | 0.009 (3) | 0.001 (3) |
C15 | 0.045 (3) | 0.061 (4) | 0.046 (3) | 0.002 (3) | 0.022 (3) | 0.003 (3) |
C16 | 0.030 (3) | 0.049 (4) | 0.051 (3) | −0.003 (3) | 0.014 (3) | 0.005 (3) |
C17 | 0.037 (3) | 0.039 (3) | 0.029 (3) | 0.006 (2) | 0.007 (2) | 0.000 (3) |
C18 | 0.027 (3) | 0.048 (3) | 0.031 (3) | 0.005 (3) | 0.007 (2) | −0.007 (3) |
C19 | 0.052 (4) | 0.048 (4) | 0.039 (3) | 0.014 (3) | 0.014 (3) | −0.003 (3) |
C20 | 0.068 (4) | 0.053 (4) | 0.049 (4) | 0.025 (3) | 0.005 (3) | 0.005 (3) |
C21 | 0.046 (3) | 0.037 (4) | 0.066 (4) | 0.019 (3) | −0.005 (3) | −0.015 (3) |
C22 | 0.030 (3) | 0.060 (4) | 0.068 (4) | 0.004 (3) | 0.011 (3) | −0.028 (3) |
C23 | 0.030 (3) | 0.055 (4) | 0.044 (3) | 0.000 (3) | 0.007 (2) | −0.013 (3) |
C24 | 0.059 (4) | 0.057 (4) | 0.073 (4) | −0.020 (3) | 0.022 (3) | −0.028 (3) |
C25 | 0.064 (4) | 0.042 (4) | 0.073 (4) | 0.000 (3) | 0.014 (3) | 0.005 (3) |
C26 | 0.078 (5) | 0.064 (5) | 0.094 (6) | 0.005 (4) | 0.016 (4) | 0.004 (5) |
C27 | 0.121 (6) | 0.072 (5) | 0.127 (6) | −0.018 (5) | 0.036 (5) | −0.027 (5) |
C28 | 0.153 (8) | 0.114 (7) | 0.090 (6) | −0.001 (6) | 0.019 (5) | 0.043 (5) |
F1—C21 | 1.373 (6) | C11—C16 | 1.377 (6) |
N1—C1 | 1.404 (5) | C11—C12 | 1.393 (6) |
N1—C12 | 1.409 (5) | C12—C13 | 1.401 (6) |
N1—C9 | 1.431 (5) | C13—C14 | 1.379 (6) |
N2—C10 | 1.372 (5) | C13—H13 | 0.9300 |
N2—C1 | 1.378 (5) | C14—C15 | 1.373 (6) |
N2—H2 | 0.8600 | C14—H14 | 0.9300 |
N3—C17 | 1.144 (5) | C15—C16 | 1.377 (6) |
N4—C26 | 1.313 (7) | C15—H15 | 0.9300 |
N4—C28 | 1.441 (7) | C16—H16 | 0.9300 |
N4—C27 | 1.457 (7) | C18—C23 | 1.379 (6) |
O1—C5 | 1.218 (5) | C18—C19 | 1.387 (6) |
O2—C10 | 1.213 (5) | C19—C20 | 1.376 (7) |
O3—C26 | 1.221 (7) | C19—H19 | 0.9300 |
C1—C2 | 1.335 (6) | C20—C21 | 1.352 (7) |
C2—C17 | 1.428 (6) | C20—H20 | 0.9300 |
C2—C3 | 1.528 (6) | C21—C22 | 1.366 (7) |
C3—C4 | 1.496 (6) | C22—C23 | 1.372 (7) |
C3—C18 | 1.516 (6) | C22—H22 | 0.9300 |
C3—H3 | 0.9800 | C23—H23 | 0.9300 |
C4—C9 | 1.333 (5) | C24—H24A | 0.9600 |
C4—C5 | 1.482 (6) | C24—H24B | 0.9600 |
C5—C6 | 1.500 (6) | C24—H24C | 0.9600 |
C6—C7 | 1.539 (6) | C25—H25A | 0.9600 |
C6—H6A | 0.9700 | C25—H25B | 0.9600 |
C6—H6B | 0.9700 | C25—H25C | 0.9600 |
C7—C8 | 1.526 (6) | C26—H26 | 0.9300 |
C7—C24 | 1.530 (6) | C27—H27A | 0.9600 |
C7—C25 | 1.532 (6) | C27—H27B | 0.9600 |
C8—C9 | 1.502 (6) | C27—H27C | 0.9600 |
C8—H8A | 0.9700 | C28—H28A | 0.9600 |
C8—H8B | 0.9700 | C28—H28B | 0.9600 |
C10—C11 | 1.455 (6) | C28—H28C | 0.9600 |
C1—N1—C12 | 120.0 (4) | C14—C13—H13 | 120.3 |
C1—N1—C9 | 116.6 (3) | C12—C13—H13 | 120.3 |
C12—N1—C9 | 123.1 (3) | C15—C14—C13 | 121.0 (4) |
C10—N2—C1 | 126.7 (4) | C15—C14—H14 | 119.5 |
C10—N2—H2 | 116.6 | C13—C14—H14 | 119.5 |
C1—N2—H2 | 116.6 | C14—C15—C16 | 120.0 (5) |
C26—N4—C28 | 121.8 (6) | C14—C15—H15 | 120.0 |
C26—N4—C27 | 119.6 (6) | C16—C15—H15 | 120.0 |
C28—N4—C27 | 118.5 (6) | C15—C16—C11 | 120.2 (5) |
C2—C1—N2 | 124.4 (4) | C15—C16—H16 | 119.9 |
C2—C1—N1 | 120.1 (4) | C11—C16—H16 | 119.9 |
N2—C1—N1 | 115.5 (4) | N3—C17—C2 | 175.7 (5) |
C1—C2—C17 | 122.4 (4) | C23—C18—C19 | 117.4 (5) |
C1—C2—C3 | 121.2 (4) | C23—C18—C3 | 121.5 (4) |
C17—C2—C3 | 116.4 (4) | C19—C18—C3 | 121.0 (4) |
C4—C3—C18 | 116.8 (4) | C20—C19—C18 | 120.9 (5) |
C4—C3—C2 | 107.1 (4) | C20—C19—H19 | 119.6 |
C18—C3—C2 | 112.0 (4) | C18—C19—H19 | 119.6 |
C4—C3—H3 | 106.8 | C21—C20—C19 | 119.0 (5) |
C18—C3—H3 | 106.8 | C21—C20—H20 | 120.5 |
C2—C3—H3 | 106.8 | C19—C20—H20 | 120.5 |
C9—C4—C5 | 120.4 (4) | C20—C21—C22 | 122.6 (5) |
C9—C4—C3 | 122.8 (4) | C20—C21—F1 | 119.6 (6) |
C5—C4—C3 | 116.7 (4) | C22—C21—F1 | 117.7 (5) |
O1—C5—C4 | 120.5 (5) | C21—C22—C23 | 117.5 (5) |
O1—C5—C6 | 121.5 (4) | C21—C22—H22 | 121.3 |
C4—C5—C6 | 118.0 (4) | C23—C22—H22 | 121.3 |
C5—C6—C7 | 113.6 (4) | C22—C23—C18 | 122.5 (5) |
C5—C6—H6A | 108.8 | C22—C23—H23 | 118.7 |
C7—C6—H6A | 108.8 | C18—C23—H23 | 118.7 |
C5—C6—H6B | 108.8 | C7—C24—H24A | 109.5 |
C7—C6—H6B | 108.8 | C7—C24—H24B | 109.5 |
H6A—C6—H6B | 107.7 | H24A—C24—H24B | 109.5 |
C8—C7—C24 | 109.1 (4) | C7—C24—H24C | 109.5 |
C8—C7—C25 | 111.2 (4) | H24A—C24—H24C | 109.5 |
C24—C7—C25 | 108.8 (4) | H24B—C24—H24C | 109.5 |
C8—C7—C6 | 106.7 (4) | C7—C25—H25A | 109.5 |
C24—C7—C6 | 110.1 (4) | C7—C25—H25B | 109.5 |
C25—C7—C6 | 110.9 (4) | H25A—C25—H25B | 109.5 |
C9—C8—C7 | 112.5 (4) | C7—C25—H25C | 109.5 |
C9—C8—H8A | 109.1 | H25A—C25—H25C | 109.5 |
C7—C8—H8A | 109.1 | H25B—C25—H25C | 109.5 |
C9—C8—H8B | 109.1 | O3—C26—N4 | 126.0 (7) |
C7—C8—H8B | 109.1 | O3—C26—H26 | 117.0 |
H8A—C8—H8B | 107.8 | N4—C26—H26 | 117.0 |
C4—C9—N1 | 119.0 (4) | N4—C27—H27A | 109.5 |
C4—C9—C8 | 122.0 (4) | N4—C27—H27B | 109.5 |
N1—C9—C8 | 118.6 (4) | H27A—C27—H27B | 109.5 |
O2—C10—N2 | 121.7 (4) | N4—C27—H27C | 109.5 |
O2—C10—C11 | 123.5 (4) | H27A—C27—H27C | 109.5 |
N2—C10—C11 | 114.7 (4) | H27B—C27—H27C | 109.5 |
C16—C11—C12 | 120.3 (4) | N4—C28—H28A | 109.5 |
C16—C11—C10 | 119.2 (4) | N4—C28—H28B | 109.5 |
C12—C11—C10 | 120.3 (4) | H28A—C28—H28B | 109.5 |
C11—C12—C13 | 119.1 (4) | N4—C28—H28C | 109.5 |
C11—C12—N1 | 119.1 (4) | H28A—C28—H28C | 109.5 |
C13—C12—N1 | 121.7 (4) | H28B—C28—H28C | 109.5 |
C14—C13—C12 | 119.4 (4) | ||
C10—N2—C1—C2 | 174.2 (5) | C7—C8—C9—N1 | −143.2 (4) |
C10—N2—C1—N1 | −8.0 (7) | C1—N2—C10—O2 | 176.6 (4) |
C12—N1—C1—C2 | −161.4 (4) | C1—N2—C10—C11 | −6.6 (7) |
C9—N1—C1—C2 | 24.1 (6) | O2—C10—C11—C16 | 9.4 (8) |
C12—N1—C1—N2 | 20.6 (6) | N2—C10—C11—C16 | −167.3 (4) |
C9—N1—C1—N2 | −153.9 (4) | O2—C10—C11—C12 | −174.1 (5) |
N2—C1—C2—C17 | 4.3 (7) | N2—C10—C11—C12 | 9.2 (6) |
N1—C1—C2—C17 | −173.5 (4) | C16—C11—C12—C13 | 2.3 (7) |
N2—C1—C2—C3 | −174.9 (4) | C10—C11—C12—C13 | −174.1 (4) |
N1—C1—C2—C3 | 7.3 (7) | C16—C11—C12—N1 | 179.3 (4) |
C1—C2—C3—C4 | −32.0 (6) | C10—C11—C12—N1 | 2.8 (7) |
C17—C2—C3—C4 | 148.8 (4) | C1—N1—C12—C11 | −18.4 (6) |
C1—C2—C3—C18 | 97.3 (5) | C9—N1—C12—C11 | 155.7 (4) |
C17—C2—C3—C18 | −82.0 (5) | C1—N1—C12—C13 | 158.4 (4) |
C18—C3—C4—C9 | −97.6 (5) | C9—N1—C12—C13 | −27.4 (6) |
C2—C3—C4—C9 | 28.9 (6) | C11—C12—C13—C14 | −3.4 (7) |
C18—C3—C4—C5 | 85.6 (5) | N1—C12—C13—C14 | 179.7 (4) |
C2—C3—C4—C5 | −148.0 (4) | C12—C13—C14—C15 | 1.6 (8) |
C9—C4—C5—O1 | 175.5 (4) | C13—C14—C15—C16 | 1.4 (8) |
C3—C4—C5—O1 | −7.6 (6) | C14—C15—C16—C11 | −2.5 (8) |
C9—C4—C5—C6 | −5.2 (6) | C12—C11—C16—C15 | 0.7 (7) |
C3—C4—C5—C6 | 171.6 (4) | C10—C11—C16—C15 | 177.1 (5) |
O1—C5—C6—C7 | 154.2 (4) | C4—C3—C18—C23 | −125.8 (5) |
C4—C5—C6—C7 | −25.0 (6) | C2—C3—C18—C23 | 110.3 (5) |
C5—C6—C7—C8 | 53.6 (5) | C4—C3—C18—C19 | 56.8 (6) |
C5—C6—C7—C24 | 171.9 (4) | C2—C3—C18—C19 | −67.1 (5) |
C5—C6—C7—C25 | −67.6 (5) | C23—C18—C19—C20 | −1.8 (7) |
C24—C7—C8—C9 | −174.1 (4) | C3—C18—C19—C20 | 175.7 (4) |
C25—C7—C8—C9 | 65.9 (5) | C18—C19—C20—C21 | 0.9 (8) |
C6—C7—C8—C9 | −55.2 (5) | C19—C20—C21—C22 | −0.2 (8) |
C5—C4—C9—N1 | 175.3 (4) | C19—C20—C21—F1 | −177.6 (5) |
C3—C4—C9—N1 | −1.3 (6) | C20—C21—C22—C23 | 0.4 (8) |
C5—C4—C9—C8 | 3.3 (7) | F1—C21—C22—C23 | 177.9 (4) |
C3—C4—C9—C8 | −173.4 (4) | C21—C22—C23—C18 | −1.4 (7) |
C1—N1—C9—C4 | −27.4 (6) | C19—C18—C23—C22 | 2.1 (7) |
C12—N1—C9—C4 | 158.3 (4) | C3—C18—C23—C22 | −175.4 (4) |
C1—N1—C9—C8 | 144.9 (4) | C28—N4—C26—O3 | 179.5 (7) |
C12—N1—C9—C8 | −29.4 (6) | C27—N4—C26—O3 | −3.3 (11) |
C7—C8—C9—C4 | 28.8 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.86 | 2.06 | 2.8628 (3) | 155 |
C22—H22···O1ii | 0.93 | 2.35 | 3.2625 (3) | 168 |
Symmetry codes: (i) −x, y, −z+1/2; (ii) x, −y−1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C25H20FN3O2·C3H7NO |
Mr | 486.54 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 36.140 (15), 11.701 (5), 11.780 (5) |
β (°) | 103.122 (6) |
V (Å3) | 4851 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.26 × 0.13 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.976, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12335, 4262, 1649 |
Rint | 0.115 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.191, 1.00 |
No. of reflections | 4262 |
No. of parameters | 325 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.26 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.86 | 2.06 | 2.8628 (3) | 155.00 |
C22—H22···O1ii | 0.93 | 2.35 | 3.2625 (3) | 168.00 |
Symmetry codes: (i) −x, y, −z+1/2; (ii) x, −y−1, z−1/2. |
The pyrido[1,2-a]pyrimidine core has been a successful motif for the development of biologically interesting molecules. Compounds containing the pyrido[1,2-a]pyrimidine ring system have been used as analgesics (Hermecz & Meszaros, 1988), antiallergics (Doria et al., 1983), antiasthmatics, antipsychotics (Colpaert, 2003), gastrointestinal protective (Knoll et al., 1987), neurotropic and stress-protecting agents (Kozlovskaya et al., 1995). Moreover, some examples are key intermediates for the synthesis of rutaecarpine alkaloids and several are neutral hydrogen chloride acceptors in organic synthesis (Hermecz et al., 1996, and references therein). The discovery of quinolino[1,2-a]quinazoline including imidazo[1,2-a]pyridine moiety as new potential pharmacological molecules may be of great significance. We report herein the crystal structure of the title compound, (I).
In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987). It contains one C25H20FN3O2 molecule and one C3H7NO molecule.
Rings A (N1/C1—C4/C9), B (C4—C9) and C (N1/N2/C1/C10—C12) are not planar, having total puckering amplitudes, QT, of 0.467 (2), 0.504 (3) and 0.193 (2) Å, respectively [φ = 158.80 (7)°, θ = 154.08 (5)°; φ = 3.15 (5)°, θ = 122.37 (5)° and φ = 157.13 (17)°, θ = 79.02 (16)°, respectively] (Cremer & Pople, 1975). Rings A and C have boat conformations, while ring B adopts an envelope conformation with atom C7 displaced by 0.698 (3) Å from the plane of the other ring atoms. Rings D (C11—C16) and E (C18—C23) are, of course, planar and they are oriented at a dihedral angle of 74.86 (2)°.
In the crystal structure, intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they seem to be effective in the stabilization of the structure.