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The title compound, C25H20ClN3O2·C3H7NO, was synthesized by the reaction of 4-chloro­benzaldehyde, 2-(5,5-dimethyl-3-oxocyclo­hex-1-enylamino)benzoic acid and malononitrile in ethyl­ene glycol under microwave irradiation. The dihydro­pyridine and pyrimidine rings both adopt boat conformations. The cyclo­hexene ring adopts an envelope conformation. In the crystal structure, the main mol­ecules exist as N—H...O hydrogen-bonded dimers. The crystal packing is further stabilized by C—H...O and C—H...π inter­actions. The N,N-dimethyl­formamide mol­ecules lie within a channel formed by the quinolino[1,2-a]quinazoline mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054037/ci2492sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054037/ci2492Isup2.hkl
Contains datablock I

CCDC reference: 674074

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.074
  • wR factor = 0.216
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 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 ... 1.42 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C3 = ... S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 60
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 3 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). 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.

The asymmetric unit of the title compound (Fig. 1) contains one C25H20ClN3O2 molecule and one C3H7NO molecule. In the main molecule, the dihydropyridine ring adopts a boat conformation, with the atoms C3 and N1 deviating from the C1/C2/C9/C4 plane by 0.356 (6) and 0.272 (5) Å, respectively. The pyrimidine ring adopts a flattened boat conformation, with the atoms C10 and N1 deviating from the C1/N2/C12/C11 plane by 0.084 (6) and 0.223 (5) Å, respectively. The cyclohexene ring adopts an envelop conformation, with the atom C7 deviating from the C4/C5/C6/C8/C9 plane by 0.709 (6) Å. The dihedral angle between the C1/C2/C9/C4 and C18—C23 planes is 85.2 (2)°, and that between the C1/N2/C12/C11 and C11—C16 planes is 9.5 (1)°.

In the crystal structure, the main molecules exist as N—H···O hydrogen-bonded dimers. The crystal packing is further stabilized by C—H···O and C—H···π interactions (Table 1). The N,N-dimethylformamide molecules lie within a channel formed by the C25H20ClN3O2 molecules (Fig.2).

Related literature top

For related literature, see: Colpaert (2003); Doria et al. (1983); Hermecz et al. (1996); Hermecz & Meszaros (1988); Knoll et al. (1987); Kozlovskaya et al. (1995).

Experimental top

The title compound was prepared by the reaction of 4-chlorobenzaldehyde (0.141 g, 1 mmol), 2-(5,5-dimethyl-3-oxocyclohex-1-enylamino)benzoic acid (0.259 g, 1 mmol) with malononitrile (0.066 g, 1 mmol) in ethylene glycol (2.0 ml) at 393 K under microwave irradiation (maximum power 200 W, initial power 100 W) for 6 min (yield; 0.370 g, 86%, m.p. 513–515 K). Single crystals suitable for X-ray analysis were obtained from an ethanol-DMF solution by slow evaporation.

Refinement top

H atoms were positioned geometrically (N—H = 0.86 Å and C—H = 0.93–0.98 Å) and treated as riding, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C,N) for others. Non-H atoms of the solvent molecule were restrained to have the same Uij components within 0.01 Å2.

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 compound, showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.
8-(4-Chlorophenyl)-11,11-dimethyl-5,9-dioxo-6,8,9,10,11,12-hexahydro- 5H-quinolino[1,2-a]quinazoline-7-carbonitrile N,N-dimethylformamide solvate top
Crystal data top
C25H20ClN3O2·C3H7NOF(000) = 2112
Mr = 502.99Dx = 1.348 Mg m3
Monoclinic, C2/cMelting point = 513–515 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 36.340 (15) ÅCell parameters from 2136 reflections
b = 11.780 (5) Åθ = 2.4–25.3°
c = 11.870 (5) ŵ = 0.19 mm1
β = 102.714 (5)°T = 298 K
V = 4957 (4) Å3Block, colourless
Z = 80.23 × 0.14 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4326 independent reflections
Radiation source: fine-focus sealed tube2288 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
ϕ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 4243
Tmin = 0.957, Tmax = 0.981k = 1311
12316 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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1126P)2]
where P = (Fo2 + 2Fc2)/3
4326 reflections(Δ/σ)max = 0.001
325 parametersΔρmax = 0.34 e Å3
60 restraintsΔρmin = 0.42 e Å3
Crystal data top
C25H20ClN3O2·C3H7NOV = 4957 (4) Å3
Mr = 502.99Z = 8
Monoclinic, C2/cMo Kα radiation
a = 36.340 (15) ŵ = 0.19 mm1
b = 11.780 (5) ÅT = 298 K
c = 11.870 (5) Å0.23 × 0.14 × 0.10 mm
β = 102.714 (5)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4326 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2288 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.981Rint = 0.063
12316 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07460 restraints
wR(F2) = 0.216H-atom parameters constrained
S = 1.02Δρmax = 0.34 e Å3
4326 reflectionsΔρmin = 0.42 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
Cl10.22931 (4)0.20405 (11)0.35844 (12)0.0610 (4)
N10.10967 (9)0.6994 (3)0.4721 (3)0.0318 (8)
N20.05505 (9)0.6470 (3)0.3342 (3)0.0377 (9)
H20.04430.63460.26310.045*
N30.09005 (14)0.6117 (4)0.0656 (4)0.0663 (13)
N40.0483 (2)0.0499 (6)0.5512 (7)0.120 (2)
O10.22370 (9)0.7976 (3)0.3680 (3)0.0526 (9)
O20.00184 (9)0.6354 (3)0.3812 (3)0.0583 (10)
O30.04761 (18)0.0973 (5)0.4284 (6)0.1298 (19)
C10.09373 (11)0.6650 (3)0.3591 (4)0.0307 (10)
C20.11552 (11)0.6560 (4)0.2798 (4)0.0330 (10)
C30.15792 (11)0.6684 (3)0.3142 (4)0.0334 (10)
H30.16600.70580.24990.040*
C40.16683 (11)0.7482 (3)0.4158 (4)0.0318 (10)
C50.20159 (12)0.8182 (4)0.4284 (4)0.0374 (11)
C60.20743 (12)0.9120 (4)0.5151 (4)0.0434 (12)
H6A0.22040.97400.48650.052*
H6B0.22360.88490.58610.052*
C70.17098 (12)0.9572 (4)0.5417 (4)0.0406 (11)
C80.15012 (13)0.8553 (4)0.5792 (4)0.0401 (11)
H8A0.16480.82520.65120.048*
H8B0.12600.88040.59260.048*
C90.14360 (11)0.7626 (3)0.4891 (3)0.0306 (10)
C100.03270 (12)0.6470 (4)0.4115 (4)0.0412 (11)
C110.05214 (11)0.6549 (4)0.5329 (4)0.0357 (10)
C120.09081 (11)0.6765 (3)0.5618 (4)0.0326 (10)
C130.10988 (13)0.6722 (4)0.6773 (4)0.0393 (11)
H130.13590.68280.69790.047*
C140.08950 (13)0.6519 (4)0.7605 (4)0.0478 (12)
H140.10200.65140.83790.057*
C150.05093 (14)0.6324 (4)0.7322 (5)0.0560 (14)
H150.03770.61980.78960.067*
C160.03289 (14)0.6318 (4)0.6192 (4)0.0503 (13)
H160.00720.61570.59930.060*
C170.09971 (13)0.6297 (4)0.1621 (4)0.0415 (11)
C180.17739 (12)0.5544 (3)0.3316 (4)0.0335 (10)
C190.19864 (12)0.5168 (4)0.2540 (4)0.0401 (11)
H190.20190.56510.19510.048*
C200.21478 (12)0.4114 (4)0.2618 (4)0.0439 (12)
H200.22870.38820.20890.053*
C210.21002 (12)0.3403 (4)0.3495 (4)0.0410 (11)
C220.18959 (13)0.3743 (4)0.4295 (4)0.0449 (12)
H220.18670.32590.48890.054*
C230.17380 (13)0.4804 (4)0.4195 (4)0.0418 (12)
H230.16020.50370.47340.050*
C240.17994 (15)1.0424 (4)0.6416 (5)0.0585 (14)
H24A0.15681.07030.65780.088*
H24B0.19411.10460.62060.088*
H24C0.19451.00550.70900.088*
C250.14643 (14)1.0169 (4)0.4364 (5)0.0555 (14)
H25A0.12361.04370.45570.083*
H25B0.14030.96420.37330.083*
H25C0.16001.07990.41440.083*
C260.0489 (3)0.0566 (8)0.5279 (10)0.125 (3)
H260.05030.10750.58860.150*
C270.0500 (3)0.0870 (9)0.6655 (9)0.163 (3)
H27A0.04840.16830.66670.244*
H27B0.07330.06280.71430.244*
H27C0.02930.05500.69300.244*
C280.0440 (3)0.1374 (7)0.4606 (9)0.144 (3)
H28A0.04350.21110.49480.217*
H28B0.02080.12510.40480.217*
H28C0.06480.13310.42320.217*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0635 (9)0.0489 (8)0.0656 (9)0.0194 (6)0.0034 (7)0.0071 (7)
N10.0321 (19)0.038 (2)0.027 (2)0.0028 (16)0.0105 (16)0.0018 (16)
N20.030 (2)0.050 (2)0.032 (2)0.0033 (16)0.0035 (17)0.0042 (17)
N30.076 (3)0.087 (3)0.035 (3)0.000 (3)0.009 (2)0.003 (2)
N40.135 (5)0.089 (4)0.131 (5)0.005 (4)0.017 (4)0.021 (4)
O10.0463 (19)0.067 (2)0.053 (2)0.0070 (16)0.0300 (18)0.0006 (18)
O20.0293 (19)0.090 (3)0.053 (2)0.0075 (17)0.0044 (16)0.0061 (19)
O30.158 (5)0.098 (4)0.134 (5)0.008 (3)0.033 (4)0.011 (3)
C10.027 (2)0.032 (2)0.030 (2)0.0022 (17)0.0016 (19)0.0009 (18)
C20.033 (2)0.040 (2)0.026 (2)0.0052 (19)0.0060 (19)0.0004 (18)
C30.032 (2)0.044 (3)0.026 (2)0.0015 (19)0.0108 (19)0.0036 (19)
C40.030 (2)0.039 (2)0.029 (2)0.0024 (18)0.0115 (19)0.0019 (19)
C50.034 (2)0.038 (3)0.042 (3)0.0014 (19)0.011 (2)0.007 (2)
C60.032 (3)0.043 (3)0.055 (3)0.006 (2)0.011 (2)0.001 (2)
C70.040 (3)0.043 (3)0.041 (3)0.005 (2)0.013 (2)0.002 (2)
C80.043 (3)0.046 (3)0.034 (3)0.002 (2)0.015 (2)0.008 (2)
C90.032 (2)0.034 (2)0.025 (2)0.0053 (18)0.0035 (19)0.0029 (18)
C100.030 (3)0.047 (3)0.047 (3)0.005 (2)0.008 (2)0.002 (2)
C110.027 (2)0.041 (3)0.040 (3)0.0006 (19)0.009 (2)0.002 (2)
C120.033 (2)0.032 (2)0.035 (3)0.0010 (18)0.012 (2)0.0017 (19)
C130.039 (3)0.045 (3)0.034 (3)0.002 (2)0.010 (2)0.002 (2)
C140.048 (3)0.069 (3)0.028 (3)0.008 (2)0.010 (2)0.006 (2)
C150.049 (3)0.077 (4)0.049 (3)0.002 (3)0.026 (3)0.012 (3)
C160.042 (3)0.067 (3)0.046 (3)0.004 (2)0.018 (3)0.006 (3)
C170.046 (3)0.050 (3)0.028 (3)0.003 (2)0.008 (2)0.000 (2)
C180.037 (2)0.037 (3)0.028 (2)0.0010 (19)0.010 (2)0.0007 (19)
C190.039 (3)0.047 (3)0.038 (3)0.003 (2)0.017 (2)0.000 (2)
C200.038 (3)0.055 (3)0.042 (3)0.006 (2)0.017 (2)0.008 (2)
C210.039 (3)0.041 (3)0.042 (3)0.007 (2)0.006 (2)0.008 (2)
C220.053 (3)0.046 (3)0.036 (3)0.010 (2)0.010 (2)0.008 (2)
C230.045 (3)0.053 (3)0.031 (3)0.011 (2)0.017 (2)0.003 (2)
C240.065 (4)0.053 (3)0.060 (4)0.016 (3)0.018 (3)0.019 (3)
C250.052 (3)0.047 (3)0.066 (4)0.005 (2)0.010 (3)0.004 (3)
C260.133 (5)0.091 (5)0.142 (6)0.002 (5)0.012 (5)0.029 (5)
C270.181 (7)0.156 (7)0.143 (7)0.010 (6)0.015 (7)0.042 (6)
C280.158 (7)0.105 (6)0.166 (7)0.002 (5)0.027 (6)0.015 (6)
Geometric parameters (Å, º) top
Cl1—C211.745 (5)C11—C161.389 (6)
N1—C11.398 (5)C11—C121.395 (6)
N1—C121.413 (5)C12—C131.395 (6)
N1—C91.417 (5)C13—C141.380 (6)
N2—C101.352 (5)C13—H130.93
N2—C11.388 (5)C14—C151.387 (6)
N2—H20.86C14—H140.93
N3—C171.142 (6)C15—C161.357 (7)
N4—C261.286 (10)C15—H150.93
N4—C271.414 (11)C16—H160.93
N4—C281.473 (10)C18—C231.387 (6)
O1—C51.214 (5)C18—C191.398 (6)
O2—C101.235 (5)C19—C201.368 (6)
O3—C261.266 (10)C19—H190.9300
C1—C21.360 (6)C20—C211.376 (6)
C2—C171.424 (6)C20—H200.9300
C2—C31.512 (6)C21—C221.388 (6)
C3—C41.506 (6)C22—C231.370 (6)
C3—C181.511 (6)C22—H220.93
C3—H30.98C23—H230.93
C4—C91.349 (5)C24—H24A0.96
C4—C51.488 (6)C24—H24B0.96
C5—C61.493 (6)C24—H24C0.96
C6—C71.524 (6)C25—H25A0.96
C6—H6A0.97C25—H25B0.96
C6—H6B0.97C25—H25C0.96
C7—C241.533 (6)C26—H260.93
C7—C81.536 (6)C27—H27A0.96
C7—C251.537 (7)C27—H27B0.96
C8—C91.510 (6)C27—H27C0.96
C8—H8A0.97C28—H28A0.96
C8—H8B0.97C28—H28B0.96
C10—C111.462 (6)C28—H28C0.96
C1—N1—C12120.0 (3)C14—C13—H13120.6
C1—N1—C9116.9 (3)C12—C13—H13120.6
C12—N1—C9123.0 (3)C13—C14—C15121.9 (5)
C10—N2—C1125.9 (4)C13—C14—H14119.1
C10—N2—H2117.0C15—C14—H14119.1
C1—N2—H2117.0C16—C15—C14118.9 (4)
C26—N4—C27120.6 (9)C16—C15—H15120.5
C26—N4—C28122.0 (9)C14—C15—H15120.5
C27—N4—C28117.3 (8)C15—C16—C11121.1 (5)
C2—C1—N2123.9 (4)C15—C16—H16119.5
C2—C1—N1120.3 (4)C11—C16—H16119.5
N2—C1—N1115.8 (3)N3—C17—C2173.8 (5)
C1—C2—C17121.7 (4)C23—C18—C19117.0 (4)
C1—C2—C3121.3 (4)C23—C18—C3122.8 (4)
C17—C2—C3117.0 (4)C19—C18—C3120.1 (4)
C4—C3—C18115.7 (3)C20—C19—C18122.3 (4)
C4—C3—C2107.7 (3)C20—C19—H19118.9
C18—C3—C2111.7 (3)C18—C19—H19118.9
C4—C3—H3107.1C19—C20—C21118.7 (4)
C18—C3—H3107.1C19—C20—H20120.6
C2—C3—H3107.1C21—C20—H20120.6
C9—C4—C5120.2 (4)C20—C21—C22121.1 (4)
C9—C4—C3122.6 (4)C20—C21—Cl1119.4 (3)
C5—C4—C3117.0 (3)C22—C21—Cl1119.5 (4)
O1—C5—C4119.2 (4)C23—C22—C21118.8 (4)
O1—C5—C6122.9 (4)C23—C22—H22120.6
C4—C5—C6117.9 (4)C21—C22—H22120.6
C5—C6—C7113.8 (4)C22—C23—C18122.1 (4)
C5—C6—H6A108.8C22—C23—H23118.9
C7—C6—H6A108.8C18—C23—H23118.9
C5—C6—H6B108.8C7—C24—H24A109.5
C7—C6—H6B108.8C7—C24—H24B109.5
H6A—C6—H6B107.7H24A—C24—H24B109.5
C6—C7—C24110.0 (4)C7—C24—H24C109.5
C6—C7—C8107.1 (4)H24A—C24—H24C109.5
C24—C7—C8108.7 (4)H24B—C24—H24C109.5
C6—C7—C25111.5 (4)C7—C25—H25A109.5
C24—C7—C25108.5 (4)C7—C25—H25B109.5
C8—C7—C25111.0 (4)H25A—C25—H25B109.5
C9—C8—C7111.7 (3)C7—C25—H25C109.5
C9—C8—H8A109.3H25A—C25—H25C109.5
C7—C8—H8A109.3H25B—C25—H25C109.5
C9—C8—H8B109.3O3—C26—N4124.8 (10)
C7—C8—H8B109.3O3—C26—H26117.6
H8A—C8—H8B107.9N4—C26—H26117.6
C4—C9—N1119.3 (4)N4—C27—H27A109.5
C4—C9—C8121.6 (4)N4—C27—H27B109.5
N1—C9—C8118.5 (3)H27A—C27—H27B109.5
O2—C10—N2121.7 (4)N4—C27—H27C109.5
O2—C10—C11122.3 (4)H27A—C27—H27C109.5
N2—C10—C11115.9 (4)H27B—C27—H27C109.5
C16—C11—C12119.9 (4)N4—C28—H28A109.5
C16—C11—C10120.2 (4)N4—C28—H28B109.5
C12—C11—C10119.8 (4)H28A—C28—H28B109.5
C11—C12—C13119.4 (4)N4—C28—H28C109.5
C11—C12—N1118.6 (4)H28A—C28—H28C109.5
C13—C12—N1122.0 (4)H28B—C28—H28C109.5
C14—C13—C12118.8 (4)
C10—N2—C1—C2175.0 (4)C7—C8—C9—N1144.2 (4)
C10—N2—C1—N18.0 (6)C1—N2—C10—O2176.6 (4)
C12—N1—C1—C2160.9 (4)C1—N2—C10—C116.9 (6)
C9—N1—C1—C222.9 (5)O2—C10—C11—C1610.0 (7)
C12—N1—C1—N222.0 (5)N2—C10—C11—C16166.4 (4)
C9—N1—C1—N2154.3 (3)O2—C10—C11—C12175.2 (4)
N2—C1—C2—C171.7 (7)N2—C10—C11—C128.3 (6)
N1—C1—C2—C17175.2 (4)C16—C11—C12—C131.4 (6)
N2—C1—C2—C3175.5 (4)C10—C11—C12—C13173.4 (4)
N1—C1—C2—C37.6 (6)C16—C11—C12—N1179.8 (4)
C1—C2—C3—C430.2 (5)C10—C11—C12—N15.0 (6)
C17—C2—C3—C4152.5 (4)C1—N1—C12—C1120.8 (5)
C1—C2—C3—C1897.9 (5)C9—N1—C12—C11155.2 (4)
C17—C2—C3—C1879.5 (5)C1—N1—C12—C13157.6 (4)
C18—C3—C4—C999.9 (5)C9—N1—C12—C1326.4 (6)
C2—C3—C4—C925.8 (5)C11—C12—C13—C143.1 (6)
C18—C3—C4—C584.3 (5)N1—C12—C13—C14178.6 (4)
C2—C3—C4—C5150.0 (4)C12—C13—C14—C152.0 (7)
C9—C4—C5—O1173.9 (4)C13—C14—C15—C160.8 (8)
C3—C4—C5—O110.1 (6)C14—C15—C16—C112.6 (8)
C9—C4—C5—C66.7 (6)C12—C11—C16—C151.5 (7)
C3—C4—C5—C6169.3 (4)C10—C11—C16—C15176.2 (5)
O1—C5—C6—C7154.3 (4)C4—C3—C18—C2357.6 (5)
C4—C5—C6—C725.1 (6)C2—C3—C18—C2366.1 (5)
C5—C6—C7—C24173.0 (4)C4—C3—C18—C19125.7 (4)
C5—C6—C7—C855.0 (5)C2—C3—C18—C19110.7 (4)
C5—C6—C7—C2566.6 (5)C23—C18—C19—C201.2 (7)
C6—C7—C8—C955.7 (5)C3—C18—C19—C20175.7 (4)
C24—C7—C8—C9174.6 (4)C18—C19—C20—C210.3 (7)
C25—C7—C8—C966.2 (5)C19—C20—C21—C220.6 (7)
C5—C4—C9—N1176.8 (4)C19—C20—C21—Cl1178.3 (4)
C3—C4—C9—N11.1 (6)C20—C21—C22—C230.5 (7)
C5—C4—C9—C85.0 (6)Cl1—C21—C22—C23178.3 (4)
C3—C4—C9—C8170.6 (4)C21—C22—C23—C180.5 (7)
C1—N1—C9—C427.3 (5)C19—C18—C23—C221.3 (7)
C12—N1—C9—C4156.5 (4)C3—C18—C23—C22175.6 (4)
C1—N1—C9—C8144.7 (4)C27—N4—C26—O3179.7 (9)
C12—N1—C9—C831.4 (5)C28—N4—C26—O33.3 (15)
C7—C8—C9—C427.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.862.042.849 (5)157
C20—H20···O1ii0.932.383.269 (6)160
C13—H13···Cg1iii0.932.843.530 (5)132
C26—H26···Cg2iv0.932.963.720 (10)140
Symmetry codes: (i) x, y, z+1/2; (ii) x+1/2, y1/2, z+1/2; (iii) x+1/2, y+3/2, z+1/2; (iv) x, y1, z.

Experimental details

Crystal data
Chemical formulaC25H20ClN3O2·C3H7NO
Mr502.99
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)36.340 (15), 11.780 (5), 11.870 (5)
β (°) 102.714 (5)
V3)4957 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.23 × 0.14 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.957, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
12316, 4326, 2288
Rint0.063
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.216, 1.02
No. of reflections4326
No. of parameters325
No. of restraints60
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.42

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···O2i0.862.042.849 (5)157
C20—H20···O1ii0.932.383.269 (6)160
C13—H13···Cg1iii0.932.843.530 (5)132
C26—H26···Cg2iv0.932.963.720 (10)140
Symmetry codes: (i) x, y, z+1/2; (ii) x+1/2, y1/2, z+1/2; (iii) x+1/2, y+3/2, z+1/2; (iv) x, y1, z.
 

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