N-(2,5-Dimeth-oxy-phen-yl)-6-nitro-quinazolin-4-amine.

In the title mol-ecule, C16H14N4O4, the quinazoline ring is substanti-ally planar (r.m.s. deviation = 0.0129 Å) and forms a dihedral angle of 2.73 (8)° with the benzene ring. The conformation of the mol-ecule is stabilized by an intra-molecular C-H⋯N hydrogen bond. In the crystal, mol-ecules are linked into chains running parallel to the b axis by C-H⋯O hydrogen bonds. In addition, π-π stacking is observed between dimethoxy-substituted and nitro-substituted benzene rings, with centroid-centroid distances in the range 3.6438 (10)-3.7148 (10) Å.

Related literature

For the biological activity of quinazoline derivatives, see: Arfan et al. (2008 ▶); Sheng-Li et al. (2005 ▶); Kung et al. (1999 ▶); Ram et al. (1990 ▶); Misra et al. (1981 ▶); Hess et al. (1968 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H14N4O4

M = 326.31

Triclinic,

a = 7.2440 (7) Å

b = 10.2832 (10) Å

c = 11.1622 (11) Å

α = 72.475 (2)°

β = 83.663 (2)°

γ = 70.429 (2)°

V = 747.05 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.29 × 0.19 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.970, T max = 0.984

8510 measured reflections

2792 independent reflections

2249 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.05

2792 reflections

224 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812048878/rz5029sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048878/rz5029Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048878/rz5029Isup3.cml

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

C16H14N4O4	Z = 2
Mr = 326.31	F(000) = 340
Triclinic, P1	Dx = 1.451 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2440 (7) Å	Cell parameters from 2914 reflections
b = 10.2832 (10) Å	θ = 2.2–28.2°
c = 11.1622 (11) Å	µ = 0.11 mm−1
α = 72.475 (2)°	T = 298 K
β = 83.663 (2)°	Block, brown
γ = 70.429 (2)°	0.29 × 0.19 × 0.15 mm
V = 747.05 (13) Å3

Bruker SMART APEX CCD area-detector diffractometer	2792 independent reflections
Radiation source: fine-focus sealed tube	2249 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scan	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.970, Tmax = 0.984	k = −12→12
8510 measured reflections	l = −13→13

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0634P)2 + 0.1096P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2792 reflections	Δρmax = 0.18 e Å−3
224 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (3)

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.

	x	y	z	Uiso*/Ueq
O1	0.32912 (17)	0.94268 (12)	−0.22927 (10)	0.0562 (3)
O2	0.3236 (2)	1.48679 (13)	−0.24856 (12)	0.0691 (4)
O3	0.1791 (2)	0.42539 (13)	0.34841 (13)	0.0830 (5)
O4	0.2239 (2)	0.50964 (14)	0.15126 (12)	0.0760 (4)
N1	0.25382 (19)	1.01670 (14)	−0.02167 (11)	0.0433 (3)
H1A	0.271 (2)	0.936 (2)	−0.0378 (16)	0.057 (5)*
N2	0.1798 (2)	1.14710 (13)	0.12319 (12)	0.0509 (4)
N3	0.1201 (2)	1.04595 (13)	0.34070 (12)	0.0490 (3)
N4	0.1950 (2)	0.52243 (14)	0.25729 (13)	0.0527 (4)
C1	0.3302 (2)	1.07924 (17)	−0.23984 (14)	0.0458 (4)
C2	0.3659 (2)	1.1756 (2)	−0.34973 (15)	0.0538 (4)
H2B	0.3923	1.1489	−0.4239	0.065*
C3	0.3625 (2)	1.31047 (19)	−0.35023 (15)	0.0553 (4)
H3B	0.3870	1.3742	−0.4244	0.066*
C4	0.3231 (2)	1.35085 (17)	−0.24107 (15)	0.0498 (4)
C5	0.2860 (2)	1.25646 (16)	−0.12990 (15)	0.0470 (4)
H5A	0.2590	1.2843	−0.0563	0.056*
C6	0.2894 (2)	1.12074 (16)	−0.12903 (13)	0.0413 (3)
C7	0.2062 (2)	1.02516 (15)	0.09734 (13)	0.0383 (3)
C8	0.1392 (3)	1.14894 (17)	0.24328 (15)	0.0543 (4)
H8A	0.1223	1.2361	0.2589	0.065*
C9	0.1398 (2)	0.91960 (15)	0.31559 (13)	0.0388 (3)
C10	0.1148 (2)	0.80460 (16)	0.41591 (14)	0.0444 (4)
H10A	0.0859	0.8167	0.4959	0.053*
C11	0.1322 (2)	0.67639 (16)	0.39744 (14)	0.0440 (4)
H11A	0.1156	0.6007	0.4638	0.053*
C12	0.1754 (2)	0.66082 (14)	0.27654 (14)	0.0399 (3)
C13	0.2004 (2)	0.76883 (15)	0.17581 (13)	0.0388 (3)
H13A	0.2281	0.7546	0.0965	0.047*
C14	0.18346 (19)	0.90156 (14)	0.19406 (13)	0.0358 (3)
C15	0.3816 (3)	0.8934 (2)	−0.33839 (17)	0.0663 (5)
H15A	0.3811	0.7959	−0.3187	0.099*
H15B	0.5102	0.8974	−0.3664	0.099*
H15C	0.2889	0.9534	−0.4036	0.099*
C16	0.2820 (3)	1.5289 (2)	−0.1356 (2)	0.0781 (6)
H16A	0.2891	1.6242	−0.1515	0.117*
H16B	0.3760	1.4631	−0.0730	0.117*
H16C	0.1528	1.5278	−0.1061	0.117*

	U11	U22	U33	U12	U13	U23
O1	0.0745 (8)	0.0609 (7)	0.0399 (6)	−0.0283 (6)	0.0097 (5)	−0.0198 (5)
O2	0.0911 (9)	0.0502 (7)	0.0614 (8)	−0.0316 (7)	0.0063 (7)	−0.0012 (6)
O3	0.1479 (14)	0.0451 (7)	0.0626 (8)	−0.0462 (8)	0.0084 (8)	−0.0107 (6)
O4	0.1248 (12)	0.0602 (8)	0.0589 (8)	−0.0407 (8)	0.0150 (8)	−0.0326 (6)
N1	0.0579 (8)	0.0396 (7)	0.0338 (7)	−0.0191 (6)	0.0037 (5)	−0.0098 (5)
N2	0.0736 (9)	0.0398 (7)	0.0417 (7)	−0.0227 (6)	0.0058 (6)	−0.0123 (6)
N3	0.0688 (9)	0.0436 (7)	0.0419 (7)	−0.0235 (6)	0.0078 (6)	−0.0189 (6)
N4	0.0701 (9)	0.0434 (7)	0.0505 (8)	−0.0224 (7)	0.0030 (7)	−0.0181 (6)
C1	0.0430 (8)	0.0549 (9)	0.0386 (8)	−0.0169 (7)	0.0003 (6)	−0.0105 (7)
C2	0.0529 (9)	0.0717 (11)	0.0335 (8)	−0.0209 (8)	0.0025 (7)	−0.0098 (7)
C3	0.0542 (10)	0.0614 (10)	0.0399 (9)	−0.0218 (8)	−0.0014 (7)	0.0048 (7)
C4	0.0484 (9)	0.0474 (9)	0.0461 (9)	−0.0165 (7)	−0.0019 (7)	−0.0003 (7)
C5	0.0495 (9)	0.0470 (8)	0.0405 (8)	−0.0164 (7)	0.0007 (7)	−0.0060 (7)
C6	0.0394 (8)	0.0469 (8)	0.0336 (8)	−0.0143 (6)	−0.0016 (6)	−0.0048 (6)
C7	0.0402 (8)	0.0403 (8)	0.0349 (7)	−0.0138 (6)	0.0008 (6)	−0.0109 (6)
C8	0.0794 (12)	0.0412 (8)	0.0498 (9)	−0.0251 (8)	0.0078 (8)	−0.0199 (7)
C9	0.0414 (8)	0.0414 (8)	0.0374 (8)	−0.0154 (6)	0.0023 (6)	−0.0152 (6)
C10	0.0564 (9)	0.0474 (8)	0.0331 (7)	−0.0210 (7)	0.0079 (6)	−0.0146 (6)
C11	0.0518 (9)	0.0432 (8)	0.0375 (8)	−0.0204 (7)	0.0040 (6)	−0.0078 (6)
C12	0.0441 (8)	0.0357 (7)	0.0430 (8)	−0.0140 (6)	0.0001 (6)	−0.0140 (6)
C13	0.0444 (8)	0.0410 (8)	0.0334 (7)	−0.0137 (6)	0.0012 (6)	−0.0142 (6)
C14	0.0359 (7)	0.0377 (7)	0.0341 (7)	−0.0119 (6)	0.0007 (6)	−0.0105 (6)
C15	0.0800 (13)	0.0786 (12)	0.0517 (10)	−0.0321 (10)	0.0150 (9)	−0.0323 (9)
C16	0.1048 (16)	0.0540 (11)	0.0800 (14)	−0.0356 (11)	0.0166 (12)	−0.0196 (10)

O1—C1	1.3761 (19)	C4—C5	1.389 (2)
O1—C15	1.4234 (19)	C5—C6	1.385 (2)
O2—C4	1.376 (2)	C5—H5A	0.9300
O2—C16	1.423 (2)	C7—C14	1.4430 (19)
O3—N4	1.2179 (17)	C8—H8A	0.9300
O4—N4	1.2176 (17)	C9—C10	1.409 (2)
N1—C7	1.3564 (18)	C9—C14	1.4115 (19)
N1—C6	1.4112 (18)	C10—C11	1.358 (2)
N1—H1A	0.868 (19)	C10—H10A	0.9300
N2—C7	1.3182 (19)	C11—C12	1.396 (2)
N2—C8	1.345 (2)	C11—H11A	0.9300
N3—C8	1.302 (2)	C12—C13	1.367 (2)
N3—C9	1.3687 (18)	C13—C14	1.4033 (19)
N4—C12	1.4608 (18)	C13—H13A	0.9300
C1—C2	1.387 (2)	C15—H15A	0.9600
C1—C6	1.397 (2)	C15—H15B	0.9600
C2—C3	1.377 (2)	C15—H15C	0.9600
C2—H2B	0.9300	C16—H16A	0.9600
C3—C4	1.374 (2)	C16—H16B	0.9600
C3—H3B	0.9300	C16—H16C	0.9600
C1—O1—C15	117.06 (13)	N3—C8—H8A	115.4
C4—O2—C16	116.73 (13)	N2—C8—H8A	115.4
C7—N1—C6	129.76 (13)	N3—C9—C10	117.95 (13)
C7—N1—H1A	118.8 (12)	N3—C9—C14	122.40 (13)
C6—N1—H1A	111.4 (12)	C10—C9—C14	119.65 (12)
C7—N2—C8	117.26 (13)	C11—C10—C9	120.95 (13)
C8—N3—C9	114.77 (13)	C11—C10—H10A	119.5
O4—N4—O3	123.00 (13)	C9—C10—H10A	119.5
O4—N4—C12	118.81 (13)	C10—C11—C12	118.47 (13)
O3—N4—C12	118.18 (13)	C10—C11—H11A	120.8
O1—C1—C2	125.36 (14)	C12—C11—H11A	120.8
O1—C1—C6	115.44 (13)	C13—C12—C11	123.04 (13)
C2—C1—C6	119.20 (15)	C13—C12—N4	118.71 (13)
C3—C2—C1	120.74 (15)	C11—C12—N4	118.25 (13)
C3—C2—H2B	119.6	C12—C13—C14	118.91 (13)
C1—C2—H2B	119.6	C12—C13—H13A	120.5
C4—C3—C2	119.96 (14)	C14—C13—H13A	120.5
C4—C3—H3B	120.0	C13—C14—C9	118.98 (12)
C2—C3—H3B	120.0	C13—C14—C7	125.30 (12)
C3—C4—O2	116.71 (14)	C9—C14—C7	115.72 (12)
C3—C4—C5	120.38 (15)	O1—C15—H15A	109.5
O2—C4—C5	122.91 (15)	O1—C15—H15B	109.5
C6—C5—C4	119.81 (15)	H15A—C15—H15B	109.5
C6—C5—H5A	120.1	O1—C15—H15C	109.5
C4—C5—H5A	120.1	H15A—C15—H15C	109.5
C5—C6—C1	119.91 (13)	H15B—C15—H15C	109.5
C5—C6—N1	124.48 (13)	O2—C16—H16A	109.5
C1—C6—N1	115.61 (13)	O2—C16—H16B	109.5
N2—C7—N1	119.40 (13)	H16A—C16—H16B	109.5
N2—C7—C14	120.64 (13)	O2—C16—H16C	109.5
N1—C7—C14	119.95 (12)	H16A—C16—H16C	109.5
N3—C8—N2	129.14 (14)	H16B—C16—H16C	109.5
C15—O1—C1—C2	4.4 (2)	C7—N2—C8—N3	−0.5 (3)
C15—O1—C1—C6	−176.33 (14)	C8—N3—C9—C10	−178.01 (14)
O1—C1—C2—C3	179.65 (14)	C8—N3—C9—C14	1.9 (2)
C6—C1—C2—C3	0.4 (2)	N3—C9—C10—C11	179.96 (14)
C1—C2—C3—C4	−0.2 (2)	C14—C9—C10—C11	0.0 (2)
C2—C3—C4—O2	179.56 (14)	C9—C10—C11—C12	0.0 (2)
C2—C3—C4—C5	−0.1 (2)	C10—C11—C12—C13	−0.2 (2)
C16—O2—C4—C3	179.79 (16)	C10—C11—C12—N4	179.70 (13)
C16—O2—C4—C5	−0.6 (2)	O4—N4—C12—C13	−3.3 (2)
C3—C4—C5—C6	0.2 (2)	O3—N4—C12—C13	177.54 (14)
O2—C4—C5—C6	−179.49 (14)	O4—N4—C12—C11	176.73 (14)
C4—C5—C6—C1	0.1 (2)	O3—N4—C12—C11	−2.4 (2)
C4—C5—C6—N1	−179.94 (13)	C11—C12—C13—C14	0.5 (2)
O1—C1—C6—C5	−179.67 (13)	N4—C12—C13—C14	−179.45 (12)
C2—C1—C6—C5	−0.4 (2)	C12—C13—C14—C9	−0.5 (2)
O1—C1—C6—N1	0.34 (19)	C12—C13—C14—C7	179.88 (13)
C2—C1—C6—N1	179.66 (13)	N3—C9—C14—C13	−179.70 (13)
C7—N1—C6—C5	1.8 (2)	C10—C9—C14—C13	0.2 (2)
C7—N1—C6—C1	−178.23 (14)	N3—C9—C14—C7	0.0 (2)
C8—N2—C7—N1	−177.84 (14)	C10—C9—C14—C7	179.89 (12)
C8—N2—C7—C14	2.6 (2)	N2—C7—C14—C13	177.34 (13)
C6—N1—C7—N2	2.7 (2)	N1—C7—C14—C13	−2.2 (2)
C6—N1—C7—C14	−177.71 (13)	N2—C7—C14—C9	−2.3 (2)
C9—N3—C8—N2	−1.8 (3)	N1—C7—C14—C9	178.10 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···N2	0.93	2.22	2.833 (2)	123
C8—H8A···O3i	0.93	2.60	3.490 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯N2	0.93	2.22	2.833 (2)	123
C8—H8A⋯O3i	0.93	2.60	3.490 (2)	161

Symmetry code: (i) .