4-Hydro­xy-1-methyl-2-oxo-N-(4-oxo-2-propyl-3,4-di­hydro­quinazolin-3-yl)-1,2-di­hydro­quinoline-3-carbox­amide

Shishkina, S.V.; Shishkin, O.V.; Ukrainets, I.V.; Jaradat, N.A.; Gorokhova, O.V.

doi:10.1107/S0108270100003887

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4-Hydroxy-1-methyl-2-oxo-N-(4-oxo-2-propyl-3,4-dihydroquinazolin-3-yl)-1,2-dihydroquinoline-3-carboxamide

S. V. Shishkina, O. V. Shishkin, I. V. Ukrainets, N. A. Jaradat and O. V. Gorokhova

The two bicyclic fragments of the title compound, C₂₂H₂₀N₄O₄, are individually planar and are turned with respect to each other by 77.8 (2)°. The formation of intramolecular O-H

O and N-H

O hydrogen bonds causes considerable changes in the bond lengths within the amidopyridine fragment.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100003887/qb0196sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003887/qb0196Isup2.hkl Contains datablock I

CCDC reference: 144723

Comment top

In the present paper, we report the results of an investigation of the molecular and crystal structures of the (2-propyl-4-oxoquinazoline-3-yl)amide of 1-methyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid, (I), which may be used as efficient anti-inflammatory remedies (Ukrainets et al., 1993, 1994). Both bicyclic fragments of the molecule are planar. The amide group O3═C10—N2 lies in the plane of the pyridine ring [the C1—C2—C10—N2 torsion angle is 2.8 (2)°]. This is caused by formation of O2—H2O···O3 and N2—H2N···O1 hydrogen bonds [H2O···O3 1.73 (4) Å, O2—H2O···O3 151 (4)°; H2N···O1 1.83 (3) Å, N2—H2N···O1 140 (2)°]. Two planar fragments are turned with respect to each other [the C10—N2—N3—C18 torsion angle is -77.8 (2)°]. The propyl substituent at the C11 atom and the C11—N4 bond have an sp orientation [the N4—C11—C20—C21 torsion angle is -0.4 (2)°]. Such an arrangement of the alkyl group, apparently, results from repulsion between the H atoms of the propyl substituent and the amide fragment. This assumption is confirmed by the presence of the shortened intramolecular contacts H20A···N2 2.60 Å and H20B···N2 2.61 Å (van der Waals radii sum is 2.66 Å; Zefirov et al., 1995). The formation of the intramolecular hydrogen bonds causes change of bond lengths within the amidopyridine fragment. Similar changes in the bond lengths were observed in the related structure 3-benzoyl-1-ethyl-4-hydroxy-2-quinolone (Borowiec et al., 1996). This effect may be explained by some contribution of the enole resonance form into the total structure of molecule.

Computing details top

Data collection: P3/PC (Siemens, 1989); cell refinement: P3/PC; data reduction: XDISK (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

4-Hydroxy-1-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid(4-oxo-2-propyl-4H-quinazolin-3-yl)-amide top

Crystal data top

C₂₂H₂₀N₄O₄	F(000) = 848
M_r = 404.42	D_x = 1.378 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.474 (3) Å	Cell parameters from 24 reflections
b = 15.213 (4) Å	θ = 10–11°
c = 10.684 (3) Å	µ = 0.10 mm⁻¹
β = 105.95 (3)°	T = 293 K
V = 1949.4 (9) Å³	Needle, yellow
Z = 4	0.40 × 0.20 × 0.10 mm

Data collection top

Siemens P3/PC diffractometer	R_int = 0.016
Radiation source: fine-focus sealed tube	θ_max = 30.1°, θ_min = 2.2°
Graphite monochromator	h = −17→16
q/2q scans	k = −21→0
5749 measured reflections	l = 0→15
5477 independent reflections	2 standard reflections every 98 reflections
3031 reflections with I > 2σ(I)	intensity decay: 5%

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Calculated w = 1/[σ²(F_o²) + (0.1328P)²] where P = (F_o² + 2F_c²)/3
5477 reflections	(Δ/σ)_max < 0.001
351 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₂H₂₀N₄O₄	V = 1949.4 (9) Å³
M_r = 404.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.474 (3) Å	µ = 0.10 mm⁻¹
b = 15.213 (4) Å	T = 293 K
c = 10.684 (3) Å	0.40 × 0.20 × 0.10 mm
β = 105.95 (3)°

Data collection top

Siemens P3/PC diffractometer	R_int = 0.016
5749 measured reflections	2 standard reflections every 98 reflections
5477 independent reflections	intensity decay: 5%
3031 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.30 e Å⁻³
5477 reflections	Δρ_min = −0.21 e Å⁻³
351 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

	x	y	z	U_iso*/U_eq
N1	0.35536 (12)	0.23075 (9)	0.73254 (15)	0.0450 (4)
N2	0.20889 (12)	0.44261 (9)	0.87749 (16)	0.0440 (4)
H2N	0.1947 (19)	0.3855 (17)	0.889 (2)	0.062 (6)*
N3	0.15142 (12)	0.51069 (9)	0.91643 (14)	0.0387 (3)
N4	−0.01563 (12)	0.59026 (9)	0.87356 (14)	0.0416 (3)
O1	0.24143 (12)	0.27785 (8)	0.85092 (16)	0.0562 (4)
O2	0.43750 (12)	0.48575 (10)	0.66834 (15)	0.0545 (4)
H2O	0.402 (3)	0.517 (2)	0.706 (3)	0.095 (10)*
O3	0.30127 (11)	0.53882 (8)	0.78486 (13)	0.0479 (3)
O4	0.30571 (11)	0.54157 (9)	1.08335 (13)	0.0510 (3)
C1	0.30670 (14)	0.29704 (10)	0.78559 (18)	0.0404 (4)
C2	0.33493 (13)	0.38686 (10)	0.76288 (15)	0.0364 (3)
C3	0.41016 (14)	0.40450 (11)	0.69226 (17)	0.0403 (4)
C4	0.46072 (14)	0.33379 (13)	0.64006 (17)	0.0446 (4)
C5	0.53652 (17)	0.35068 (18)	0.5670 (2)	0.0574 (5)
H5	0.556 (2)	0.4064 (18)	0.553 (3)	0.069 (7)*
C6	0.58119 (19)	0.2822 (2)	0.5140 (2)	0.0692 (7)
H6	0.6318 (19)	0.2966 (14)	0.461 (2)	0.057 (6)*
C7	0.5506 (2)	0.1964 (2)	0.5338 (2)	0.0702 (7)
H7	0.579 (2)	0.148 (2)	0.504 (3)	0.084 (8)*
C8	0.47812 (19)	0.17822 (17)	0.6060 (2)	0.0599 (6)
H8	0.460 (2)	0.1178 (19)	0.615 (2)	0.063 (6)*
C9	0.43096 (13)	0.24762 (12)	0.66070 (17)	0.0446 (4)
C10	0.28179 (13)	0.46167 (10)	0.80851 (16)	0.0369 (3)
C11	0.04287 (14)	0.52801 (10)	0.84441 (16)	0.0374 (4)
C12	0.03415 (14)	0.64369 (10)	0.97955 (17)	0.0402 (4)
C13	−0.02928 (19)	0.71136 (13)	1.0131 (2)	0.0553 (5)
H13	−0.104 (2)	0.7183 (15)	0.966 (2)	0.056 (6)*
C14	0.0170 (2)	0.76502 (15)	1.1176 (2)	0.0662 (6)
H14	−0.024 (2)	0.812 (2)	1.145 (3)	0.089 (9)*
C15	0.1285 (2)	0.75555 (14)	1.1877 (2)	0.0648 (6)
H15	0.161 (2)	0.7964 (18)	1.260 (3)	0.076 (7)*
C16	0.1923 (2)	0.68963 (13)	1.1571 (2)	0.0519 (5)
H16	0.264 (2)	0.6842 (16)	1.203 (2)	0.064 (7)*
C17	0.14486 (14)	0.63285 (10)	1.05313 (16)	0.0392 (4)
C18	0.21054 (14)	0.56011 (10)	1.02416 (17)	0.0386 (4)
C19	0.3245 (2)	0.14056 (13)	0.7555 (3)	0.0654 (6)
H19A	0.262 (3)	0.142 (2)	0.800 (4)	0.119 (12)*
H19B	0.386 (3)	0.107 (2)	0.796 (3)	0.095 (9)*
H19C	0.303 (3)	0.107 (3)	0.669 (4)	0.119 (12)*
C20	−0.00446 (17)	0.47018 (12)	0.72914 (19)	0.0456 (4)
H20A	0.0017 (19)	0.4096 (15)	0.759 (2)	0.056 (6)*
H20B	0.043 (2)	0.4740 (16)	0.672 (3)	0.068 (7)*
C21	−0.12326 (19)	0.49134 (15)	0.6544 (2)	0.0562 (5)
H21A	−0.172 (2)	0.4820 (17)	0.711 (3)	0.073 (7)*
H21B	−0.134 (2)	0.5524 (16)	0.619 (2)	0.063 (6)*
C22	−0.1643 (3)	0.4297 (2)	0.5407 (3)	0.0804 (8)
H22A	−0.244 (4)	0.445 (2)	0.485 (4)	0.124 (12)*
H22B	−0.167 (3)	0.365 (3)	0.576 (4)	0.125 (13)*
H22C	−0.118 (3)	0.442 (2)	0.482 (4)	0.106 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0425 (7)	0.0344 (7)	0.0575 (9)	0.0041 (6)	0.0127 (7)	−0.0086 (6)
N2	0.0464 (8)	0.0296 (7)	0.0641 (9)	0.0038 (6)	0.0289 (7)	−0.0017 (6)
N3	0.0404 (7)	0.0310 (6)	0.0496 (8)	0.0038 (5)	0.0206 (6)	−0.0030 (6)
N4	0.0415 (7)	0.0374 (7)	0.0489 (8)	0.0039 (6)	0.0174 (6)	0.0004 (6)
O1	0.0572 (8)	0.0354 (6)	0.0882 (10)	−0.0030 (5)	0.0405 (7)	−0.0026 (6)
O2	0.0561 (8)	0.0490 (8)	0.0684 (9)	−0.0019 (6)	0.0338 (7)	0.0038 (6)
O3	0.0588 (8)	0.0329 (6)	0.0596 (8)	0.0017 (5)	0.0290 (6)	0.0009 (5)
O4	0.0439 (7)	0.0515 (8)	0.0570 (8)	0.0033 (5)	0.0127 (6)	0.0069 (6)
C1	0.0342 (8)	0.0330 (8)	0.0543 (10)	0.0017 (6)	0.0127 (7)	−0.0052 (7)
C2	0.0350 (8)	0.0339 (7)	0.0421 (8)	0.0022 (6)	0.0136 (6)	−0.0040 (6)
C3	0.0349 (7)	0.0426 (9)	0.0438 (9)	0.0021 (6)	0.0117 (7)	−0.0031 (7)
C4	0.0355 (8)	0.0549 (10)	0.0437 (9)	0.0090 (7)	0.0114 (7)	−0.0066 (7)
C5	0.0438 (10)	0.0775 (16)	0.0546 (12)	0.0081 (10)	0.0201 (9)	−0.0038 (10)
C6	0.0508 (12)	0.101 (2)	0.0608 (13)	0.0185 (12)	0.0236 (11)	−0.0128 (12)
C7	0.0583 (13)	0.0899 (18)	0.0602 (13)	0.0347 (12)	0.0125 (11)	−0.0189 (12)
C8	0.0557 (11)	0.0607 (13)	0.0593 (12)	0.0222 (10)	0.0091 (10)	−0.0125 (10)
C9	0.0358 (8)	0.0516 (10)	0.0433 (9)	0.0121 (7)	0.0055 (7)	−0.0098 (8)
C10	0.0363 (7)	0.0326 (7)	0.0432 (8)	0.0020 (6)	0.0132 (6)	−0.0023 (6)
C11	0.0409 (8)	0.0344 (8)	0.0412 (8)	0.0005 (6)	0.0184 (7)	0.0041 (6)
C12	0.0484 (9)	0.0295 (7)	0.0488 (9)	0.0019 (6)	0.0234 (8)	0.0015 (7)
C13	0.0576 (12)	0.0428 (10)	0.0711 (13)	0.0100 (8)	0.0274 (11)	−0.0028 (9)
C14	0.0860 (16)	0.0428 (11)	0.0781 (15)	0.0095 (10)	0.0365 (13)	−0.0119 (10)
C15	0.0915 (16)	0.0443 (11)	0.0632 (13)	−0.0056 (11)	0.0290 (12)	−0.0175 (10)
C16	0.0637 (13)	0.0447 (10)	0.0493 (10)	−0.0063 (9)	0.0187 (10)	−0.0038 (8)
C17	0.0482 (9)	0.0318 (7)	0.0432 (9)	−0.0003 (6)	0.0221 (7)	0.0022 (6)
C18	0.0431 (9)	0.0337 (7)	0.0435 (9)	−0.0014 (6)	0.0195 (7)	0.0048 (6)
C19	0.0638 (14)	0.0325 (9)	0.1001 (19)	0.0013 (9)	0.0229 (14)	−0.0116 (10)
C20	0.0516 (10)	0.0412 (9)	0.0482 (10)	−0.0023 (8)	0.0209 (8)	−0.0050 (8)
C21	0.0568 (12)	0.0557 (12)	0.0540 (12)	−0.0012 (9)	0.0114 (10)	0.0031 (9)
C22	0.0816 (19)	0.095 (2)	0.0569 (14)	−0.0180 (16)	0.0057 (14)	−0.0099 (14)

Geometric parameters (Å, º) top

N1—C1	1.377 (2)	C4—C9	1.396 (3)
N1—C9	1.394 (2)	C4—C5	1.405 (3)
N1—C19	1.464 (3)	C5—C6	1.375 (3)
N2—C10	1.350 (2)	C6—C7	1.393 (4)
N2—N3	1.3869 (19)	C7—C8	1.367 (4)
N3—C11	1.386 (2)	C8—C9	1.411 (3)
N3—C18	1.403 (2)	C11—C20	1.497 (3)
N4—C11	1.285 (2)	C12—C17	1.398 (3)
N4—C12	1.394 (2)	C12—C13	1.404 (2)
O1—C1	1.244 (2)	C13—C14	1.375 (3)
O2—C3	1.326 (2)	C14—C15	1.394 (4)
O3—C10	1.2385 (19)	C15—C16	1.374 (3)
O4—C18	1.215 (2)	C16—C17	1.403 (3)
C1—C2	1.448 (2)	C17—C18	1.460 (2)
C2—C3	1.382 (2)	C20—C21	1.512 (3)
C2—C10	1.466 (2)	C21—C22	1.508 (4)
C3—C4	1.435 (2)

C1—N1—C9	122.24 (15)	N1—C9—C4	120.62 (15)
C1—N1—C19	116.83 (17)	N1—C9—C8	120.83 (19)
C9—N1—C19	120.93 (16)	C4—C9—C8	118.54 (19)
C10—N2—N3	118.99 (14)	O3—C10—N2	120.95 (14)
C11—N3—N2	118.81 (14)	O3—C10—C2	122.40 (15)
C11—N3—C18	124.52 (13)	N2—C10—C2	116.66 (14)
N2—N3—C18	116.60 (14)	N4—C11—N3	122.59 (15)
C11—N4—C12	118.09 (15)	N4—C11—C20	120.72 (16)
O1—C1—N1	119.32 (15)	N3—C11—C20	116.69 (14)
O1—C1—C2	122.83 (15)	N4—C12—C17	122.59 (14)
N1—C1—C2	117.85 (15)	N4—C12—C13	118.61 (17)
C3—C2—C1	120.49 (14)	C17—C12—C13	118.79 (16)
C3—C2—C10	117.87 (15)	C14—C13—C12	120.2 (2)
C1—C2—C10	121.59 (14)	C13—C14—C15	120.6 (2)
O2—C3—C2	122.37 (16)	C16—C15—C14	120.3 (2)
O2—C3—C4	117.40 (16)	C15—C16—C17	119.4 (2)
C2—C3—C4	120.22 (16)	C12—C17—C16	120.60 (16)
C9—C4—C5	120.53 (18)	C12—C17—C18	119.69 (15)
C9—C4—C3	118.56 (16)	C16—C17—C18	119.68 (17)
C5—C4—C3	120.89 (19)	O4—C18—N3	121.39 (15)
C6—C5—C4	120.1 (2)	O4—C18—C17	126.21 (16)
C5—C6—C7	119.2 (2)	N3—C18—C17	112.40 (14)
C8—C7—C6	121.8 (2)	C11—C20—C21	114.64 (16)
C7—C8—C9	119.9 (2)	C22—C21—C20	111.0 (2)

C10—N2—N3—C11	99.33 (19)	C3—C2—C10—O3	0.7 (2)
C10—N2—N3—C18	−77.8 (2)	C1—C2—C10—O3	−176.68 (17)
C9—N1—C1—O1	−178.62 (16)	C3—C2—C10—N2	−179.85 (16)
C19—N1—C1—O1	1.1 (3)	C1—C2—C10—N2	2.8 (2)
C9—N1—C1—C2	1.0 (2)	C12—N4—C11—N3	2.0 (2)
C19—N1—C1—C2	−179.28 (18)	C12—N4—C11—C20	−178.00 (15)
O1—C1—C2—C3	178.35 (17)	N2—N3—C11—N4	−179.50 (15)
N1—C1—C2—C3	−1.3 (2)	C18—N3—C11—N4	−2.6 (2)
O1—C1—C2—C10	−4.3 (3)	N2—N3—C11—C20	0.5 (2)
N1—C1—C2—C10	176.06 (15)	C18—N3—C11—C20	177.41 (15)
C1—C2—C3—O2	179.40 (16)	C11—N4—C12—C17	1.0 (2)
C10—C2—C3—O2	2.0 (2)	C11—N4—C12—C13	−179.36 (16)
C1—C2—C3—C4	0.3 (3)	N4—C12—C13—C14	179.65 (19)
C10—C2—C3—C4	−177.11 (15)	C17—C12—C13—C14	−0.7 (3)
O2—C3—C4—C9	−178.21 (15)	C12—C13—C14—C15	2.9 (3)
C2—C3—C4—C9	0.9 (3)	C13—C14—C15—C16	−3.1 (3)
O2—C3—C4—C5	0.3 (3)	C14—C15—C16—C17	1.2 (3)
C2—C3—C4—C5	179.38 (17)	N4—C12—C17—C16	178.39 (16)
C9—C4—C5—C6	0.7 (3)	C13—C12—C17—C16	−1.2 (2)
C3—C4—C5—C6	−177.77 (19)	N4—C12—C17—C18	−3.6 (2)
C4—C5—C6—C7	−0.1 (3)	C13—C12—C17—C18	176.83 (16)
C5—C6—C7—C8	−0.8 (4)	C15—C16—C17—C12	1.0 (3)
C6—C7—C8—C9	1.1 (4)	C15—C16—C17—C18	−177.04 (17)
C1—N1—C9—C4	0.2 (2)	C11—N3—C18—O4	−179.98 (15)
C19—N1—C9—C4	−179.48 (19)	N2—N3—C18—O4	−3.0 (2)
C1—N1—C9—C8	−179.06 (17)	C11—N3—C18—C17	0.0 (2)
C19—N1—C9—C8	1.2 (3)	N2—N3—C18—C17	176.97 (13)
C5—C4—C9—N1	−179.66 (16)	C12—C17—C18—O4	−177.15 (16)
C3—C4—C9—N1	−1.2 (2)	C16—C17—C18—O4	0.9 (3)
C5—C4—C9—C8	−0.4 (3)	C12—C17—C18—N3	2.8 (2)
C3—C4—C9—C8	178.10 (17)	C16—C17—C18—N3	−179.11 (15)
C7—C8—C9—N1	178.79 (18)	N4—C11—C20—C21	−0.4 (2)
C7—C8—C9—C4	−0.5 (3)	N3—C11—C20—C21	179.60 (16)
N3—N2—C10—O3	3.2 (3)	C11—C20—C21—C22	−179.71 (19)
N3—N2—C10—C2	−176.27 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3	0.83 (4)	1.72 (4)	2.500 (2)	155 (3)
N2—H2N···O1	0.90 (3)	1.82 (3)	2.567 (2)	139 (2)

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀N₄O₄
M_r	404.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.474 (3), 15.213 (4), 10.684 (3)
β (°)	105.95 (3)
V (Å³)	1949.4 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Siemens P3/PC diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5749, 5477, 3031
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.190, 0.96
No. of reflections	5477
No. of parameters	351
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.21

Computer programs: P3/PC (Siemens, 1989), P3/PC, XDISK (Siemens, 1991), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXL97.

Selected bond lengths (Å) top

O1—C1	1.244 (2)	C1—C2	1.448 (2)
O2—C3	1.326 (2)	C2—C3	1.382 (2)
O3—C10	1.2385 (19)	C3—C4	1.435 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3	0.83 (4)	1.72 (4)	2.500 (2)	155 (3)
N2—H2N···O1	0.90 (3)	1.82 (3)	2.567 (2)	139 (2)

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4-Hydro­xy-1-methyl-2-oxo-N-(4-oxo-2-propyl-3,4-di­hydro­quinazolin-3-yl)-1,2-di­hydro­quinoline-3-carbox­amide

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4-Hydroxy-1-methyl-2-oxo-N-(4-oxo-2-propyl-3,4-dihydroquinazolin-3-yl)-1,2-dihydroquinoline-3-carboxamide