8,8-Dimethyl-5-(4-methyl-phen-yl)-8,9-dihydro-pyrimido[4,5-b]quinoline-2,4,6(1H,3H,7H)-trione N,N-dimethyl-formamide solvate.

The title compound, C(20)H(19)N(3)O(3)·C(3)H(7)NO, was synthesized by the reaction of 6-amino-pyrimidine-2,4(1H,3H)-dione and 4-methyl-benzaldehyde with 5,5-dimethyl-1,3-cyclo-hexa-nedione in 1-butyl-3-methyl-imidazolium bromide at 363 K. The pyrimidine ring adopts a half-chair conformation while the six-membered ring fused to the pyridine ring adopts a skew-boat conformation. The dihedral angle between the pyridine ring and the attached benzene ring is 2.38(8)°

Related literature

For related literature, see: Bhuyan et al. (1999 ▶); Clercq (1986 ▶); Gangjee et al. (1999 ▶); Griengl et al. (1987 ▶); Hirota et al. (1981 ▶); Jones et al. (1979 ▶); Nasr & Gineinah (2002 ▶); Pontikis & Monneret (1994 ▶); Sasaki et al. (1980 ▶).

Experimental

Crystal data

C20H19N3O3·C3H7NO

M = 422.48

Triclinic,

a = 8.8252 (16) Å

b = 10.289 (2) Å

c = 12.316 (2) Å

α = 95.898 (3)°

β = 93.115 (3)°

γ = 94.719 (3)°

V = 1106.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 294 (2) K

0.24 × 0.16 × 0.12 mm

Data collection

Bruker SMART 1000 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.989

6083 measured reflections

4285 independent reflections

2833 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.134

S = 1.00

4285 reflections

285 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002924/cs2057sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002924/cs2057Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H19N3O3·C3H7NO	Z = 2
Mr = 422.48	F000 = 448
Triclinic, P1	Dx = 1.268 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.8252 (16) Å	Cell parameters from 2318 reflections
b = 10.289 (2) Å	θ = 2.5–26.3º
c = 12.316 (2) Å	µ = 0.09 mm−1
α = 95.898 (3)º	T = 294 (2) K
β = 93.115 (3)º	Block, colorless
γ = 94.719 (3)º	0.24 × 0.16 × 0.12 mm
V = 1106.4 (4) Å3

Bruker SMART 1000 diffractometer	4285 independent reflections
Radiation source: fine-focus sealed tube	2833 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.018
T = 294(2) K	θmax = 26.0º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.978, Tmax = 0.989	k = −10→12
6083 measured reflections	l = −15→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0627P)2 + 0.2466P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4285 reflections	Δρmax = 0.25 e Å−3
285 parameters	Δρmin = −0.23 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	0.66314 (15)	0.41510 (14)	0.49822 (12)	0.0587 (4)
O2	0.61458 (17)	0.01747 (15)	0.62264 (14)	0.0726 (5)
O3	0.1315 (2)	−0.03738 (19)	0.88397 (19)	0.1117 (8)
N1	0.63982 (17)	0.22017 (16)	0.56995 (13)	0.0485 (4)
H1	0.7300	0.2042	0.5431	0.058*
N2	0.45129 (17)	0.36219 (16)	0.58594 (14)	0.0503 (4)
H2	0.4112	0.4358	0.5704	0.060*
N3	0.24137 (17)	0.32697 (15)	0.68299 (13)	0.0475 (4)
C1	0.5892 (2)	0.33743 (19)	0.54821 (16)	0.0456 (5)
C2	0.5624 (2)	0.1225 (2)	0.62047 (16)	0.0474 (5)
C3	0.42031 (19)	0.15976 (18)	0.66859 (14)	0.0411 (4)
C4	0.3337 (2)	0.08197 (18)	0.73401 (14)	0.0404 (4)
C5	0.1967 (2)	0.12798 (18)	0.76963 (15)	0.0438 (4)
C6	0.0920 (2)	0.0536 (2)	0.83849 (18)	0.0556 (5)
C7	−0.0623 (2)	0.10073 (19)	0.85164 (18)	0.0533 (5)
H7A	−0.1091	0.0604	0.9108	0.064*
H7B	−0.1259	0.0737	0.7851	0.064*
C8	−0.0549 (2)	0.25028 (19)	0.87620 (16)	0.0473 (5)
C9	0.0437 (3)	0.2941 (2)	0.98100 (19)	0.0691 (6)
H9A	0.0456	0.3875	0.9972	0.104*
H9B	0.1455	0.2703	0.9716	0.104*
H9C	0.0023	0.2520	1.0402	0.104*
C10	−0.2145 (2)	0.2942 (2)	0.8905 (2)	0.0650 (6)
H10A	−0.2567	0.2574	0.9520	0.098*
H10B	−0.2785	0.2647	0.8256	0.098*
H10C	−0.2088	0.3882	0.9029	0.098*
C11	0.0129 (2)	0.3077 (2)	0.77834 (18)	0.0544 (5)
H11A	−0.0631	0.2944	0.7174	0.065*
H11B	0.0350	0.4016	0.7966	0.065*
C12	0.1560 (2)	0.25081 (18)	0.74199 (16)	0.0458 (5)
C13	0.36838 (19)	0.27982 (18)	0.64708 (15)	0.0420 (4)
C14	0.38754 (19)	−0.04296 (18)	0.76792 (14)	0.0398 (4)
C15	0.3251 (2)	−0.16362 (19)	0.71966 (16)	0.0503 (5)
H15	0.2520	−0.1684	0.6618	0.060*
C16	0.3704 (2)	−0.2778 (2)	0.75669 (18)	0.0558 (5)
H16	0.3266	−0.3584	0.7235	0.067*
C17	0.4790 (2)	−0.2743 (2)	0.84175 (17)	0.0530 (5)
C18	0.5257 (3)	−0.4007 (3)	0.8817 (2)	0.0871 (8)
H18A	0.6009	−0.4355	0.8362	0.131*
H18B	0.4381	−0.4632	0.8783	0.131*
H18C	0.5675	−0.3833	0.9559	0.131*
C19	0.5433 (2)	−0.1537 (2)	0.88808 (17)	0.0548 (5)
H19	0.6181	−0.1493	0.9448	0.066*
C20	0.4988 (2)	−0.0388 (2)	0.85185 (16)	0.0485 (5)
H20	0.5442	0.0417	0.8842	0.058*
O4	−0.06364 (17)	0.16079 (19)	0.51009 (14)	0.0800 (5)
N4	0.09249 (19)	0.25425 (17)	0.39330 (15)	0.0582 (5)
C21	0.0462 (2)	0.1599 (3)	0.45278 (19)	0.0658 (6)
H21	0.1016	0.0868	0.4510	0.079*
C22	0.0147 (3)	0.3718 (2)	0.3888 (3)	0.0941 (10)
H22A	−0.0687	0.3694	0.4357	0.141*
H22B	−0.0234	0.3772	0.3151	0.141*
H22C	0.0845	0.4472	0.4128	0.141*
C23	0.2201 (3)	0.2428 (3)	0.3249 (2)	0.0797 (8)
H23A	0.2674	0.1643	0.3368	0.120*
H23B	0.2928	0.3176	0.3431	0.120*
H23C	0.1846	0.2390	0.2495	0.120*

	U11	U22	U33	U12	U13	U23
O1	0.0489 (8)	0.0557 (9)	0.0800 (10)	0.0090 (6)	0.0278 (7)	0.0317 (7)
O2	0.0714 (10)	0.0658 (10)	0.0973 (12)	0.0368 (8)	0.0439 (9)	0.0436 (9)
O3	0.1149 (15)	0.0955 (14)	0.1588 (19)	0.0597 (12)	0.0936 (14)	0.0921 (14)
N1	0.0396 (8)	0.0558 (10)	0.0574 (10)	0.0151 (7)	0.0189 (7)	0.0236 (8)
N2	0.0446 (9)	0.0477 (9)	0.0676 (11)	0.0153 (7)	0.0225 (8)	0.0298 (8)
N3	0.0434 (8)	0.0466 (9)	0.0597 (10)	0.0131 (7)	0.0181 (7)	0.0249 (8)
C1	0.0395 (10)	0.0480 (11)	0.0535 (11)	0.0077 (8)	0.0124 (9)	0.0168 (9)
C2	0.0473 (11)	0.0521 (12)	0.0497 (11)	0.0165 (9)	0.0143 (9)	0.0232 (9)
C3	0.0396 (10)	0.0441 (10)	0.0441 (10)	0.0110 (8)	0.0097 (8)	0.0163 (8)
C4	0.0429 (10)	0.0408 (10)	0.0412 (10)	0.0100 (8)	0.0087 (8)	0.0132 (8)
C5	0.0440 (10)	0.0443 (11)	0.0478 (11)	0.0098 (8)	0.0142 (8)	0.0162 (8)
C6	0.0633 (13)	0.0447 (11)	0.0665 (13)	0.0131 (10)	0.0296 (11)	0.0229 (10)
C7	0.0485 (11)	0.0497 (12)	0.0646 (13)	0.0020 (9)	0.0198 (10)	0.0141 (10)
C8	0.0420 (10)	0.0464 (11)	0.0575 (12)	0.0090 (8)	0.0173 (9)	0.0138 (9)
C9	0.0749 (15)	0.0634 (15)	0.0693 (15)	0.0109 (12)	0.0075 (12)	0.0036 (12)
C10	0.0516 (12)	0.0669 (15)	0.0824 (16)	0.0141 (11)	0.0280 (11)	0.0164 (12)
C11	0.0459 (11)	0.0571 (13)	0.0687 (13)	0.0190 (9)	0.0227 (10)	0.0263 (10)
C12	0.0432 (10)	0.0462 (11)	0.0533 (11)	0.0113 (8)	0.0145 (9)	0.0194 (9)
C13	0.0376 (9)	0.0447 (11)	0.0484 (11)	0.0088 (8)	0.0120 (8)	0.0190 (8)
C14	0.0409 (9)	0.0410 (10)	0.0422 (10)	0.0103 (8)	0.0136 (8)	0.0163 (8)
C15	0.0527 (11)	0.0477 (12)	0.0514 (12)	0.0066 (9)	−0.0011 (9)	0.0113 (9)
C16	0.0631 (13)	0.0389 (11)	0.0670 (14)	0.0073 (9)	0.0069 (11)	0.0095 (10)
C17	0.0564 (12)	0.0500 (13)	0.0601 (13)	0.0194 (10)	0.0158 (10)	0.0236 (10)
C18	0.0965 (19)	0.0673 (17)	0.109 (2)	0.0288 (14)	0.0107 (16)	0.0448 (15)
C19	0.0550 (12)	0.0627 (14)	0.0508 (12)	0.0155 (10)	−0.0006 (10)	0.0198 (10)
C20	0.0520 (11)	0.0463 (11)	0.0483 (11)	0.0042 (9)	0.0019 (9)	0.0116 (9)
O4	0.0493 (9)	0.1184 (15)	0.0802 (11)	0.0195 (9)	0.0241 (8)	0.0278 (10)
N4	0.0482 (10)	0.0595 (11)	0.0705 (12)	0.0154 (8)	0.0172 (9)	0.0086 (9)
C21	0.0501 (12)	0.0872 (18)	0.0675 (15)	0.0244 (12)	0.0143 (11)	0.0229 (13)
C22	0.0639 (15)	0.0549 (15)	0.166 (3)	0.0120 (12)	0.0356 (17)	0.0052 (16)
C23	0.0733 (16)	0.0849 (18)	0.0918 (19)	0.0286 (14)	0.0400 (14)	0.0257 (15)

O1—C1	1.226 (2)	C10—H10C	0.9600
O2—C2	1.211 (2)	C11—C12	1.506 (2)
O3—C6	1.205 (2)	C11—H11A	0.9700
N1—C1	1.367 (2)	C11—H11B	0.9700
N1—C2	1.388 (2)	C14—C15	1.378 (3)
N1—H1	0.8997	C14—C20	1.382 (3)
N2—C1	1.360 (2)	C15—C16	1.383 (3)
N2—C13	1.382 (2)	C15—H15	0.9300
N2—H2	0.8952	C16—C17	1.377 (3)
N3—C13	1.337 (2)	C16—H16	0.9300
N3—C12	1.338 (2)	C17—C19	1.375 (3)
C2—C3	1.478 (2)	C17—C18	1.516 (3)
C3—C13	1.398 (2)	C18—H18A	0.9600
C3—C4	1.405 (2)	C18—H18B	0.9600
C4—C5	1.409 (2)	C18—H18C	0.9600
C4—C14	1.497 (2)	C19—C20	1.384 (3)
C5—C12	1.411 (2)	C19—H19	0.9300
C5—C6	1.503 (2)	C20—H20	0.9300
C6—C7	1.495 (3)	O4—C21	1.230 (2)
C7—C8	1.533 (3)	N4—C21	1.326 (3)
C7—H7A	0.9700	N4—C22	1.444 (3)
C7—H7B	0.9700	N4—C23	1.447 (3)
C8—C9	1.523 (3)	C21—H21	0.9300
C8—C11	1.526 (3)	C22—H22A	0.9600
C8—C10	1.528 (3)	C22—H22B	0.9600
C9—H9A	0.9600	C22—H22C	0.9600
C9—H9B	0.9600	C23—H23A	0.9600
C9—H9C	0.9600	C23—H23B	0.9600
C10—H10A	0.9600	C23—H23C	0.9600
C10—H10B	0.9600
C1—N1—C2	127.04 (15)	C12—C11—H11B	108.5
C1—N1—H1	114.5	C8—C11—H11B	108.5
C2—N1—H1	118.3	H11A—C11—H11B	107.5
C1—N2—C13	123.74 (15)	N3—C12—C5	123.18 (16)
C1—N2—H2	118.6	N3—C12—C11	114.43 (16)
C13—N2—H2	117.6	C5—C12—C11	122.38 (16)
C13—N3—C12	116.77 (15)	N3—C13—N2	114.21 (15)
O1—C1—N2	122.24 (17)	N3—C13—C3	125.32 (15)
O1—C1—N1	122.30 (16)	N2—C13—C3	120.46 (15)
N2—C1—N1	115.46 (16)	C15—C14—C20	118.52 (17)
O2—C2—N1	119.28 (17)	C15—C14—C4	121.53 (17)
O2—C2—C3	125.96 (17)	C20—C14—C4	119.91 (17)
N1—C2—C3	114.75 (16)	C14—C15—C16	120.51 (19)
C13—C3—C4	117.92 (15)	C14—C15—H15	119.7
C13—C3—C2	117.88 (15)	C16—C15—H15	119.7
C4—C3—C2	124.20 (16)	C17—C16—C15	121.3 (2)
C3—C4—C5	117.59 (16)	C17—C16—H16	119.4
C3—C4—C14	121.21 (15)	C15—C16—H16	119.4
C5—C4—C14	121.17 (15)	C19—C17—C16	117.98 (18)
C4—C5—C12	119.14 (16)	C19—C17—C18	121.7 (2)
C4—C5—C6	123.10 (16)	C16—C17—C18	120.4 (2)
C12—C5—C6	117.74 (16)	C17—C18—H18A	109.5
O3—C6—C7	121.12 (18)	C17—C18—H18B	109.5
O3—C6—C5	121.92 (19)	H18A—C18—H18B	109.5
C7—C6—C5	116.92 (17)	C17—C18—H18C	109.5
C6—C7—C8	111.96 (16)	H18A—C18—H18C	109.5
C6—C7—H7A	109.2	H18B—C18—H18C	109.5
C8—C7—H7A	109.2	C17—C19—C20	121.29 (19)
C6—C7—H7B	109.2	C17—C19—H19	119.4
C8—C7—H7B	109.2	C20—C19—H19	119.4
H7A—C7—H7B	107.9	C14—C20—C19	120.40 (19)
C9—C8—C11	111.19 (18)	C14—C20—H20	119.8
C9—C8—C10	108.88 (18)	C19—C20—H20	119.8
C11—C8—C10	109.94 (16)	C21—N4—C22	122.15 (19)
C9—C8—C7	109.80 (17)	C21—N4—C23	121.93 (19)
C11—C8—C7	106.70 (16)	C22—N4—C23	115.86 (19)
C10—C8—C7	110.32 (16)	O4—C21—N4	125.7 (2)
C8—C9—H9A	109.5	O4—C21—H21	117.2
C8—C9—H9B	109.5	N4—C21—H21	117.2
H9A—C9—H9B	109.5	N4—C22—H22A	109.5
C8—C9—H9C	109.5	N4—C22—H22B	109.5
H9A—C9—H9C	109.5	H22A—C22—H22B	109.5
H9B—C9—H9C	109.5	N4—C22—H22C	109.5
C8—C10—H10A	109.5	H22A—C22—H22C	109.5
C8—C10—H10B	109.5	H22B—C22—H22C	109.5
H10A—C10—H10B	109.5	N4—C23—H23A	109.5
C8—C10—H10C	109.5	N4—C23—H23B	109.5
H10A—C10—H10C	109.5	H23A—C23—H23B	109.5
H10B—C10—H10C	109.5	N4—C23—H23C	109.5
C12—C11—C8	114.94 (16)	H23A—C23—H23C	109.5
C12—C11—H11A	108.5	H23B—C23—H23C	109.5
C8—C11—H11A	108.5
C13—N2—C1—O1	−176.75 (19)	C13—N3—C12—C11	−178.87 (17)
C13—N2—C1—N1	3.2 (3)	C4—C5—C12—N3	0.0 (3)
C2—N1—C1—O1	−176.3 (2)	C6—C5—C12—N3	178.69 (19)
C2—N1—C1—N2	3.8 (3)	C4—C5—C12—C11	−179.04 (18)
C1—N1—C2—O2	171.4 (2)	C6—C5—C12—C11	−0.4 (3)
C1—N1—C2—C3	−9.2 (3)	C8—C11—C12—N3	−159.06 (18)
O2—C2—C3—C13	−172.7 (2)	C8—C11—C12—C5	20.1 (3)
N1—C2—C3—C13	8.0 (3)	C12—N3—C13—N2	179.51 (17)
O2—C2—C3—C4	7.0 (3)	C12—N3—C13—C3	−1.7 (3)
N1—C2—C3—C4	−172.41 (18)	C1—N2—C13—N3	175.18 (18)
C13—C3—C4—C5	2.6 (3)	C1—N2—C13—C3	−3.7 (3)
C2—C3—C4—C5	−176.97 (18)	C4—C3—C13—N3	−0.6 (3)
C13—C3—C4—C14	−175.28 (17)	C2—C3—C13—N3	179.01 (18)
C2—C3—C4—C14	5.1 (3)	C4—C3—C13—N2	178.07 (17)
C3—C4—C5—C12	−2.4 (3)	C2—C3—C13—N2	−2.3 (3)
C14—C4—C5—C12	175.53 (18)	C3—C4—C14—C15	−104.4 (2)
C3—C4—C5—C6	179.03 (18)	C5—C4—C14—C15	77.8 (2)
C14—C4—C5—C6	−3.1 (3)	C3—C4—C14—C20	77.8 (2)
C4—C5—C6—O3	13.9 (4)	C5—C4—C14—C20	−100.1 (2)
C12—C5—C6—O3	−164.7 (2)	C20—C14—C15—C16	1.7 (3)
C4—C5—C6—C7	−168.34 (19)	C4—C14—C15—C16	−176.17 (17)
C12—C5—C6—C7	13.1 (3)	C14—C15—C16—C17	−0.4 (3)
O3—C6—C7—C8	132.9 (3)	C15—C16—C17—C19	−1.0 (3)
C5—C6—C7—C8	−45.0 (3)	C15—C16—C17—C18	179.4 (2)
C6—C7—C8—C9	−59.3 (2)	C16—C17—C19—C20	1.0 (3)
C6—C7—C8—C11	61.3 (2)	C18—C17—C19—C20	−179.3 (2)
C6—C7—C8—C10	−179.26 (18)	C15—C14—C20—C19	−1.6 (3)
C9—C8—C11—C12	70.9 (2)	C4—C14—C20—C19	176.28 (17)
C10—C8—C11—C12	−168.42 (18)	C17—C19—C20—C14	0.3 (3)
C7—C8—C11—C12	−48.8 (2)	C22—N4—C21—O4	−0.6 (4)
C13—N3—C12—C5	2.0 (3)	C23—N4—C21—O4	−177.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4i	0.90	1.96	2.854 (2)	170
N2—H2···O1ii	0.90	1.97	2.846 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.90	1.96	2.854 (2)	170
N2—H2⋯O1ii	0.90	1.97	2.846 (2)	167

Symmetry codes: (i) ; (ii) .