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In the title compound, C25H20FN3O2·C3H7NO, the dihydro­pyridine and pyrimidine rings have boat conformations, while the cyclo­hexene ring adopts an envelope conformation. In the crystal structure, inter­molecular N—H...O and C—H...O hydrogen bonds link the mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045643/hk2326sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045643/hk2326Isup2.hkl
Contains datablock I

CCDC reference: 664211

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Comment top

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.

Related literature top

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).

Experimental top

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.

Refinement top

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.

Structure description top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.
8-(4-fluorophenyl)-11,11-dimethyl-5,9-dioxo-6,8,9,10,11,12-hexahydro-5H- quinolino[1,2-a]quinazoline-7-carbonitrile dimethylformamide solvate top
Crystal data top
C25H20FN3O2·C3H7NOF(000) = 2048
Mr = 486.54Dx = 1.332 Mg m3
Monoclinic, C2/cMelting point = 534–535 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 36.140 (15) ÅCell parameters from 1017 reflections
b = 11.701 (5) Åθ = 2.5–19.7°
c = 11.780 (5) ŵ = 0.09 mm1
β = 103.122 (6)°T = 298 K
V = 4851 (4) Å3Block, colorless
Z = 80.26 × 0.13 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4262 independent reflections
Radiation source: fine-focus sealed tube1649 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.115
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 4242
Tmin = 0.976, Tmax = 0.991k = 813
12335 measured reflectionsl = 1413
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.191H-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 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C25H20FN3O2·C3H7NOV = 4851 (4) Å3
Mr = 486.54Z = 8
Monoclinic, C2/cMo Kα radiation
a = 36.140 (15) ŵ = 0.09 mm1
b = 11.701 (5) ÅT = 298 K
c = 11.780 (5) Å0.26 × 0.13 × 0.10 mm
β = 103.122 (6)°
Data collection top
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 = 0.991Rint = 0.115
12335 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.191H-atom parameters constrained
S = 1.00Δρmax = 0.28 e Å3
4262 reflectionsΔρmin = 0.26 e Å3
325 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
xyzUiso*/Ueq
F10.22422 (9)0.2184 (3)0.3860 (3)0.0876 (12)
N10.11112 (9)0.6953 (3)0.4752 (3)0.0286 (9)
N20.05613 (10)0.6431 (3)0.3357 (3)0.0343 (10)
H20.04530.63030.26390.041*
N30.09081 (13)0.6056 (4)0.0661 (4)0.0578 (13)
N40.04876 (14)0.9481 (5)0.0533 (5)0.0693 (15)
O10.22506 (9)0.7939 (3)0.3657 (3)0.0506 (10)
O20.00121 (9)0.6344 (3)0.3816 (3)0.0513 (10)
O30.04920 (14)1.0979 (4)0.0674 (4)0.0983 (17)
C10.09488 (12)0.6598 (4)0.3608 (4)0.0291 (11)
C20.11659 (12)0.6478 (4)0.2838 (3)0.0284 (11)
C30.15981 (12)0.6583 (4)0.3207 (4)0.0338 (12)
H30.16820.69270.25500.041*
C40.16847 (12)0.7426 (4)0.4186 (4)0.0300 (11)
C50.20306 (13)0.8133 (4)0.4277 (4)0.0371 (12)
C60.20967 (13)0.9095 (4)0.5141 (4)0.0442 (14)
H6A0.22220.97160.48310.053*
H6B0.22670.88340.58540.053*
C70.17301 (13)0.9552 (4)0.5435 (4)0.0391 (13)
C80.15274 (13)0.8525 (4)0.5815 (4)0.0380 (12)
H8A0.16800.82260.65390.046*
H8B0.12860.87720.59600.046*
C90.14575 (12)0.7590 (4)0.4918 (4)0.0284 (11)
C100.03298 (13)0.6450 (4)0.4133 (4)0.0352 (12)
C110.05287 (12)0.6541 (4)0.5351 (4)0.0306 (11)
C120.09173 (12)0.6765 (4)0.5647 (4)0.0284 (11)
C130.11082 (13)0.6742 (4)0.6823 (4)0.0382 (13)
H130.13700.68490.70350.046*
C140.09043 (14)0.6560 (4)0.7664 (4)0.0454 (14)
H140.10290.65640.84470.055*
C150.05194 (14)0.6373 (4)0.7363 (4)0.0488 (14)
H150.03850.62680.79410.059*
C160.03329 (13)0.6341 (4)0.6207 (4)0.0424 (13)
H160.00740.61840.60030.051*
C170.10108 (13)0.6233 (4)0.1636 (4)0.0351 (12)
C180.17897 (12)0.5425 (4)0.3426 (4)0.0352 (12)
C190.17453 (14)0.4746 (4)0.4351 (4)0.0460 (14)
H190.16100.50250.48750.055*
C200.18988 (15)0.3666 (5)0.4502 (5)0.0580 (16)
H200.18650.32110.51180.070*
C210.20995 (15)0.3276 (5)0.3744 (5)0.0522 (15)
C220.21558 (13)0.3911 (5)0.2825 (5)0.0525 (16)
H220.22930.36250.23100.063*
C230.20018 (13)0.4988 (5)0.2691 (4)0.0433 (14)
H230.20420.54400.20810.052*
C240.18274 (15)1.0405 (5)0.6442 (5)0.0620 (17)
H24A0.19561.10520.62080.093*
H24B0.19901.00450.71040.093*
H24C0.15981.06550.66460.093*
C250.14790 (15)1.0147 (4)0.4378 (5)0.0600 (16)
H25A0.16141.07830.41520.090*
H25B0.12511.04160.45780.090*
H25C0.14150.96160.37430.090*
C260.05002 (18)1.0573 (6)0.0287 (7)0.079 (2)
H260.05171.10850.09000.095*
C270.0441 (2)0.8640 (6)0.0401 (6)0.105 (3)
H27A0.04330.78880.00820.158*
H27B0.06500.86940.07750.158*
H27C0.02070.87850.09610.158*
C280.0502 (2)0.9086 (7)0.1701 (6)0.120 (3)
H28A0.04840.82680.17010.181*
H28B0.02950.94100.19760.181*
H28C0.07380.93170.22030.181*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.081 (3)0.059 (2)0.112 (3)0.032 (2)0.003 (2)0.017 (2)
N10.026 (2)0.035 (2)0.025 (2)0.0005 (19)0.0064 (17)0.0030 (18)
N20.029 (2)0.043 (3)0.028 (2)0.003 (2)0.0001 (18)0.0034 (19)
N30.070 (3)0.062 (3)0.038 (3)0.002 (3)0.006 (2)0.000 (3)
N40.081 (4)0.047 (3)0.079 (4)0.003 (3)0.015 (3)0.006 (3)
O10.039 (2)0.061 (3)0.058 (2)0.0024 (19)0.0240 (18)0.0025 (19)
O20.027 (2)0.075 (3)0.049 (2)0.0054 (19)0.0022 (16)0.0020 (19)
O30.143 (5)0.073 (3)0.082 (3)0.013 (3)0.032 (3)0.011 (3)
C10.026 (3)0.031 (3)0.027 (3)0.002 (2)0.001 (2)0.001 (2)
C20.031 (3)0.031 (3)0.023 (3)0.003 (2)0.005 (2)0.001 (2)
C30.035 (3)0.038 (3)0.032 (3)0.000 (2)0.016 (2)0.002 (2)
C40.025 (3)0.034 (3)0.031 (3)0.001 (2)0.008 (2)0.001 (2)
C50.028 (3)0.042 (3)0.040 (3)0.004 (3)0.004 (2)0.006 (3)
C60.033 (3)0.047 (4)0.052 (3)0.007 (3)0.007 (2)0.005 (3)
C70.038 (3)0.036 (3)0.043 (3)0.007 (3)0.010 (2)0.004 (3)
C80.032 (3)0.045 (3)0.037 (3)0.003 (3)0.010 (2)0.006 (3)
C90.025 (3)0.029 (3)0.030 (3)0.002 (2)0.004 (2)0.003 (2)
C100.027 (3)0.036 (3)0.042 (3)0.004 (2)0.006 (2)0.002 (2)
C110.028 (3)0.032 (3)0.035 (3)0.001 (2)0.012 (2)0.003 (2)
C120.030 (3)0.026 (3)0.032 (3)0.003 (2)0.010 (2)0.001 (2)
C130.030 (3)0.046 (3)0.036 (3)0.004 (2)0.003 (2)0.003 (3)
C140.048 (3)0.057 (4)0.031 (3)0.001 (3)0.009 (3)0.001 (3)
C150.045 (3)0.061 (4)0.046 (3)0.002 (3)0.022 (3)0.003 (3)
C160.030 (3)0.049 (4)0.051 (3)0.003 (3)0.014 (3)0.005 (3)
C170.037 (3)0.039 (3)0.029 (3)0.006 (2)0.007 (2)0.000 (3)
C180.027 (3)0.048 (3)0.031 (3)0.005 (3)0.007 (2)0.007 (3)
C190.052 (4)0.048 (4)0.039 (3)0.014 (3)0.014 (3)0.003 (3)
C200.068 (4)0.053 (4)0.049 (4)0.025 (3)0.005 (3)0.005 (3)
C210.046 (3)0.037 (4)0.066 (4)0.019 (3)0.005 (3)0.015 (3)
C220.030 (3)0.060 (4)0.068 (4)0.004 (3)0.011 (3)0.028 (3)
C230.030 (3)0.055 (4)0.044 (3)0.000 (3)0.007 (2)0.013 (3)
C240.059 (4)0.057 (4)0.073 (4)0.020 (3)0.022 (3)0.028 (3)
C250.064 (4)0.042 (4)0.073 (4)0.000 (3)0.014 (3)0.005 (3)
C260.078 (5)0.064 (5)0.094 (6)0.005 (4)0.016 (4)0.004 (5)
C270.121 (6)0.072 (5)0.127 (6)0.018 (5)0.036 (5)0.027 (5)
C280.153 (8)0.114 (7)0.090 (6)0.001 (6)0.019 (5)0.043 (5)
Geometric parameters (Å, º) top
F1—C211.373 (6)C11—C161.377 (6)
N1—C11.404 (5)C11—C121.393 (6)
N1—C121.409 (5)C12—C131.401 (6)
N1—C91.431 (5)C13—C141.379 (6)
N2—C101.372 (5)C13—H130.9300
N2—C11.378 (5)C14—C151.373 (6)
N2—H20.8600C14—H140.9300
N3—C171.144 (5)C15—C161.377 (6)
N4—C261.313 (7)C15—H150.9300
N4—C281.441 (7)C16—H160.9300
N4—C271.457 (7)C18—C231.379 (6)
O1—C51.218 (5)C18—C191.387 (6)
O2—C101.213 (5)C19—C201.376 (7)
O3—C261.221 (7)C19—H190.9300
C1—C21.335 (6)C20—C211.352 (7)
C2—C171.428 (6)C20—H200.9300
C2—C31.528 (6)C21—C221.366 (7)
C3—C41.496 (6)C22—C231.372 (7)
C3—C181.516 (6)C22—H220.9300
C3—H30.9800C23—H230.9300
C4—C91.333 (5)C24—H24A0.9600
C4—C51.482 (6)C24—H24B0.9600
C5—C61.500 (6)C24—H24C0.9600
C6—C71.539 (6)C25—H25A0.9600
C6—H6A0.9700C25—H25B0.9600
C6—H6B0.9700C25—H25C0.9600
C7—C81.526 (6)C26—H260.9300
C7—C241.530 (6)C27—H27A0.9600
C7—C251.532 (6)C27—H27B0.9600
C8—C91.502 (6)C27—H27C0.9600
C8—H8A0.9700C28—H28A0.9600
C8—H8B0.9700C28—H28B0.9600
C10—C111.455 (6)C28—H28C0.9600
C1—N1—C12120.0 (4)C14—C13—H13120.3
C1—N1—C9116.6 (3)C12—C13—H13120.3
C12—N1—C9123.1 (3)C15—C14—C13121.0 (4)
C10—N2—C1126.7 (4)C15—C14—H14119.5
C10—N2—H2116.6C13—C14—H14119.5
C1—N2—H2116.6C14—C15—C16120.0 (5)
C26—N4—C28121.8 (6)C14—C15—H15120.0
C26—N4—C27119.6 (6)C16—C15—H15120.0
C28—N4—C27118.5 (6)C15—C16—C11120.2 (5)
C2—C1—N2124.4 (4)C15—C16—H16119.9
C2—C1—N1120.1 (4)C11—C16—H16119.9
N2—C1—N1115.5 (4)N3—C17—C2175.7 (5)
C1—C2—C17122.4 (4)C23—C18—C19117.4 (5)
C1—C2—C3121.2 (4)C23—C18—C3121.5 (4)
C17—C2—C3116.4 (4)C19—C18—C3121.0 (4)
C4—C3—C18116.8 (4)C20—C19—C18120.9 (5)
C4—C3—C2107.1 (4)C20—C19—H19119.6
C18—C3—C2112.0 (4)C18—C19—H19119.6
C4—C3—H3106.8C21—C20—C19119.0 (5)
C18—C3—H3106.8C21—C20—H20120.5
C2—C3—H3106.8C19—C20—H20120.5
C9—C4—C5120.4 (4)C20—C21—C22122.6 (5)
C9—C4—C3122.8 (4)C20—C21—F1119.6 (6)
C5—C4—C3116.7 (4)C22—C21—F1117.7 (5)
O1—C5—C4120.5 (5)C21—C22—C23117.5 (5)
O1—C5—C6121.5 (4)C21—C22—H22121.3
C4—C5—C6118.0 (4)C23—C22—H22121.3
C5—C6—C7113.6 (4)C22—C23—C18122.5 (5)
C5—C6—H6A108.8C22—C23—H23118.7
C7—C6—H6A108.8C18—C23—H23118.7
C5—C6—H6B108.8C7—C24—H24A109.5
C7—C6—H6B108.8C7—C24—H24B109.5
H6A—C6—H6B107.7H24A—C24—H24B109.5
C8—C7—C24109.1 (4)C7—C24—H24C109.5
C8—C7—C25111.2 (4)H24A—C24—H24C109.5
C24—C7—C25108.8 (4)H24B—C24—H24C109.5
C8—C7—C6106.7 (4)C7—C25—H25A109.5
C24—C7—C6110.1 (4)C7—C25—H25B109.5
C25—C7—C6110.9 (4)H25A—C25—H25B109.5
C9—C8—C7112.5 (4)C7—C25—H25C109.5
C9—C8—H8A109.1H25A—C25—H25C109.5
C7—C8—H8A109.1H25B—C25—H25C109.5
C9—C8—H8B109.1O3—C26—N4126.0 (7)
C7—C8—H8B109.1O3—C26—H26117.0
H8A—C8—H8B107.8N4—C26—H26117.0
C4—C9—N1119.0 (4)N4—C27—H27A109.5
C4—C9—C8122.0 (4)N4—C27—H27B109.5
N1—C9—C8118.6 (4)H27A—C27—H27B109.5
O2—C10—N2121.7 (4)N4—C27—H27C109.5
O2—C10—C11123.5 (4)H27A—C27—H27C109.5
N2—C10—C11114.7 (4)H27B—C27—H27C109.5
C16—C11—C12120.3 (4)N4—C28—H28A109.5
C16—C11—C10119.2 (4)N4—C28—H28B109.5
C12—C11—C10120.3 (4)H28A—C28—H28B109.5
C11—C12—C13119.1 (4)N4—C28—H28C109.5
C11—C12—N1119.1 (4)H28A—C28—H28C109.5
C13—C12—N1121.7 (4)H28B—C28—H28C109.5
C14—C13—C12119.4 (4)
C10—N2—C1—C2174.2 (5)C7—C8—C9—N1143.2 (4)
C10—N2—C1—N18.0 (7)C1—N2—C10—O2176.6 (4)
C12—N1—C1—C2161.4 (4)C1—N2—C10—C116.6 (7)
C9—N1—C1—C224.1 (6)O2—C10—C11—C169.4 (8)
C12—N1—C1—N220.6 (6)N2—C10—C11—C16167.3 (4)
C9—N1—C1—N2153.9 (4)O2—C10—C11—C12174.1 (5)
N2—C1—C2—C174.3 (7)N2—C10—C11—C129.2 (6)
N1—C1—C2—C17173.5 (4)C16—C11—C12—C132.3 (7)
N2—C1—C2—C3174.9 (4)C10—C11—C12—C13174.1 (4)
N1—C1—C2—C37.3 (7)C16—C11—C12—N1179.3 (4)
C1—C2—C3—C432.0 (6)C10—C11—C12—N12.8 (7)
C17—C2—C3—C4148.8 (4)C1—N1—C12—C1118.4 (6)
C1—C2—C3—C1897.3 (5)C9—N1—C12—C11155.7 (4)
C17—C2—C3—C1882.0 (5)C1—N1—C12—C13158.4 (4)
C18—C3—C4—C997.6 (5)C9—N1—C12—C1327.4 (6)
C2—C3—C4—C928.9 (6)C11—C12—C13—C143.4 (7)
C18—C3—C4—C585.6 (5)N1—C12—C13—C14179.7 (4)
C2—C3—C4—C5148.0 (4)C12—C13—C14—C151.6 (8)
C9—C4—C5—O1175.5 (4)C13—C14—C15—C161.4 (8)
C3—C4—C5—O17.6 (6)C14—C15—C16—C112.5 (8)
C9—C4—C5—C65.2 (6)C12—C11—C16—C150.7 (7)
C3—C4—C5—C6171.6 (4)C10—C11—C16—C15177.1 (5)
O1—C5—C6—C7154.2 (4)C4—C3—C18—C23125.8 (5)
C4—C5—C6—C725.0 (6)C2—C3—C18—C23110.3 (5)
C5—C6—C7—C853.6 (5)C4—C3—C18—C1956.8 (6)
C5—C6—C7—C24171.9 (4)C2—C3—C18—C1967.1 (5)
C5—C6—C7—C2567.6 (5)C23—C18—C19—C201.8 (7)
C24—C7—C8—C9174.1 (4)C3—C18—C19—C20175.7 (4)
C25—C7—C8—C965.9 (5)C18—C19—C20—C210.9 (8)
C6—C7—C8—C955.2 (5)C19—C20—C21—C220.2 (8)
C5—C4—C9—N1175.3 (4)C19—C20—C21—F1177.6 (5)
C3—C4—C9—N11.3 (6)C20—C21—C22—C230.4 (8)
C5—C4—C9—C83.3 (7)F1—C21—C22—C23177.9 (4)
C3—C4—C9—C8173.4 (4)C21—C22—C23—C181.4 (7)
C1—N1—C9—C427.4 (6)C19—C18—C23—C222.1 (7)
C12—N1—C9—C4158.3 (4)C3—C18—C23—C22175.4 (4)
C1—N1—C9—C8144.9 (4)C28—N4—C26—O3179.5 (7)
C12—N1—C9—C829.4 (6)C27—N4—C26—O33.3 (11)
C7—C8—C9—C428.8 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.862.062.8628 (3)155
C22—H22···O1ii0.932.353.2625 (3)168
Symmetry codes: (i) x, y, z+1/2; (ii) x, y1, z1/2.

Experimental details

Crystal data
Chemical formulaC25H20FN3O2·C3H7NO
Mr486.54
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)36.140 (15), 11.701 (5), 11.780 (5)
β (°) 103.122 (6)
V3)4851 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.26 × 0.13 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.976, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
12335, 4262, 1649
Rint0.115
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.191, 1.00
No. of reflections4262
No. of parameters325
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.26

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.862.062.8628 (3)155.00
C22—H22···O1ii0.932.353.2625 (3)168.00
Symmetry codes: (i) x, y, z+1/2; (ii) x, y1, z1/2.
 

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