8,8-Dimethyl-5-(4-methyl­phen­yl)-8,9-dihydro­pyrimido[4,5-b]quinoline-2,4,6(1H,3H,7H)-trione N,N-dimethyl­formamide solvate

Wang, J.; Ni, S.-N.; Shi, D.

doi:10.1107/S1600536808002924

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o606

doi:10.1107/S1600536808002924

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8,8-Dimethyl-5-(4-methylphenyl)-8,9-dihydropyrimido[4,5-b]quinoline-2,4,6(1H,3H,7H)-trione N,N-dimethylformamide solvate

Jing Wang,^a Sai-Nan Ni ^b and Daqing Shi ^c ^*

^aXuzhou Medical College, Xuzhou 221002, People's Republic of China, ^bDepartment of Chemistry, Xuzhou Normal University, Xuzhou 221116, People's Republic of China, and ^cDepartment of Chemistry and Chemical Engineering, Suzhou University, Suzhou 215123, People's Republic of China
^*Correspondence e-mail: dqshi@263.net

(Received 16 October 2007; accepted 25 January 2008; online 20 February 2008)

The title compound, C₂₀H₁₉N₃O₃·C₃H₇NO, was synthesized by the reaction of 6-aminopyrimidine-2,4(1H,3H)-dione and 4-methylbenzaldehyde with 5,5-dimethyl-1,3-cyclohexanedione in 1-butyl-3-methylimidazolium 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_r = 422.48
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.134
S = 1.00
4285 reflections
285 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) x+1, y, z; (ii) -x+1, -y+1, -z+1.

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.

Supporting information

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

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

checkCIF report

Comment top

The importance of uracil and its annelated derivatives is well recognized by synthetic (Sasaki et al., 1980; Bhuyan et al., 1999) as well as biological (Griengl et al., 1987; Pontikis et al., 1994) chemists. With the development of clinically useful anticancer and antiviral drugs (Clercq et al.,1986; Jones et al., 1979), there has recently been remarkable interest in the synthetic manipulations of uracils (Hirota et al., 1981). Pyrido[2,3-d]pyrimidines represent a heterocyclic ring system of considerable interest because of several biological activities associated with this scaffold. Some analogues have been found to act as anticancer agents inhibiting dihydrofolate reductases or tyrosine kinases (Gangjee et al., 1999), while others are known antiviral agents (Nasr et al., 2002).

The title compound was synthesized by the reaction of 6-aminopyrimidine-2,4(1H,3H)-dione and 4-methylbenzaldehyde with 5,5-dimethyl-1,3-cyclohexanedione using 1-butyl-3-methylimidazolium bromide ([bmim]Br) as solvent at 363 K.

In the title compound the pyridine ring (C13/C3/C4/C5/C12/N3) is a newly formed planar ring. The pyrimidine ring is less planar with atom C2 deviating from the C3/C1/C13/N1/N2 plane by -0.108 (3) Å (Fig. 1). The six-membered ring fused on to the pyridine ring adopts a skew-boat conformation; atoms C6, C5, C12 and C11 are coplanar, with atoms C7 and C8 deviating from the plane by -0.301 (2) and 0.458 (6) Å, respectively. The dihedral angle between the C13/C3/C4/C5/C12/N3 plane and the C3/C1/C13/N1/N2 plane is 2.38 (8) °, they are almost coplanar. The dihedral angle between the C13/C3/C4/C5/C12/N3 plane and the C14/C15/C16/C17/C19/C20 plane is 77.99 (5) °. The molecules are linked by N1—H1···O4 and N2—H2···O1 intermolecular hydrogen bonds (Table 1) to form dimers (Fig. 2).

Related literature top

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 top

The title compound was prepared by the reaction of 6-aminopyrimidine-2,4(1H,3H)-dione (2 mmol) and 4-methylaldehyde (2 mmol) with 5,5-dimethyl-1,3-cyclohexanedione (2 mmol) in [bmim]Br (2 ml) at 363 K. Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a N,N-dimethylformamide and water solution. ¹H NMR (DMSO-d₆, δ): 1.03 (6H, s, 2*CH₃), 2.35 (3H, s, CH₃), 2.40 (2H, s, CH₂), 2.74 (3H, s, CH₃), 2.90 (3H, s, CH₃), 3.01 (2H, s, CH₂), 6.89 (2H, d, J = 8.0 Hz, ArH), 7.08 (2H, d, J = 8.0 Hz, ArH), 7.96 (1H, s, CH), 11.12 (1H, s, NH), 11.88 (1H, s, NH).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing 40% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound.

8,8-Dimethyl-5-(4-methylphenyl)-8,9-dihydropyrimido[4,5-b]quinoline- 2,4,6(1H,3H,7H)-trione N,N-dimethylformamide solvate top

Crystal data top

C₂₀H₁₉N₃O₃·C₃H₇NO	Z = 2
M_r = 422.48	F(000) = 448
Triclinic, P1	D_x = 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 = 2.5–26.3°
c = 12.316 (2) Å	µ = 0.09 mm⁻¹
α = 95.898 (3)°	T = 294 K
β = 93.115 (3)°	Block, colorless
γ = 94.719 (3)°	0.24 × 0.16 × 0.12 mm
V = 1106.4 (4) Å³

Data collection top

Bruker SMART 1000 diffractometer	4285 independent reflections
Radiation source: fine-focus sealed tube	2833 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
T_min = 0.978, T_max = 0.989	k = −10→12
6083 measured reflections	l = −15→11

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0627P)² + 0.2466P] where P = (F_o² + 2F_c²)/3
4285 reflections	(Δ/σ)_max < 0.001
285 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₁₉N₃O₃·C₃H₇NO	γ = 94.719 (3)°
M_r = 422.48	V = 1106.4 (4) Å³
Triclinic, P1	Z = 2
a = 8.8252 (16) Å	Mo Kα radiation
b = 10.289 (2) Å	µ = 0.09 mm⁻¹
c = 12.316 (2) Å	T = 294 K
α = 95.898 (3)°	0.24 × 0.16 × 0.12 mm
β = 93.115 (3)°

Data collection top

Bruker SMART 1000 diffractometer	4285 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2833 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.989	R_int = 0.018
6083 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	1 restraint
wR(F²) = 0.134	H-atom parameters constrained
S = 1.00	Δρ_max = 0.25 e Å⁻³
4285 reflections	Δρ_min = −0.23 e Å⁻³
285 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉N₃O₃·C₃H₇NO
M_r	422.48
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.8252 (16), 10.289 (2), 12.316 (2)
α, β, γ (°)	95.898 (3), 93.115 (3), 94.719 (3)
V (Å³)	1106.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.24 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART 1000 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.978, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	6083, 4285, 2833
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.134, 1.00
No. of reflections	4285
No. of parameters	285
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.23

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.90	1.96	2.854 (2)	169.9
N2—H2···O1ⁱⁱ	0.90	1.97	2.846 (2)	166.6

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1.

Acknowledgements

The authors are grateful to the Foundation of the Key Laboratory of Biotechnology on Medical Plants of Jiangsu Province for financial support.

References

Bhuyan, P. J., Borah, H. N. & Sandhu, J. S. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 3083–3084. Web of Science CrossRef Google Scholar
Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Gangjee, A., Adair, O. & Queener, S. F. (1999). J. Med. Chem. 42, 2447–2455. Web of Science CrossRef PubMed CAS Google Scholar
Griengl, R., Wack, E., Schwarz, W., Streicher, W., Rosenwirth, B. & Clercq, E. D. (1987). J. Med. Chem. 30, 1199–1204. CrossRef CAS PubMed Web of Science Google Scholar
Hirota, K., Kitade, Y., Senda, S., Halat, M. J., Watanabe, K. A. & Fox, J. J. (1981). J. Org. Chem. 46, 846–851. CrossRef CAS Web of Science Google Scholar
Jones, A. S., Verhalst, G. & Walker, R. T. (1979). Tetrahedron Lett. 20, 4415–4418. CrossRef Google Scholar
Nasr, M. N. & Gineinah, M. M. (2002). Arch. Pharm. 335, 289–295. Web of Science CrossRef CAS Google Scholar
Pontikis, R. & Monneret, C. (1994). Tetrahedron Lett. 35, 4351–4354. CrossRef CAS Web of Science Google Scholar
Sasaki, T., Minamoto, K., Suzuki, T. & Yamashita, S. (1980). Tetrahedron, 36, 865–870. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

8,8-Di­methyl-5-(4-methyl­phen­yl)-8,9-di­hydro­pyrimido[4,5-b]quinoline-2,4,6(1H,3H,7H)-trione N,N-di­methyl­formamide solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

8,8-Dimethyl-5-(4-methylphenyl)-8,9-dihydropyrimido[4,5-b]quinoline-2,4,6(1H,3H,7H)-trione N,N-dimethylformamide solvate