7-Chloro-6,8-dinitro-quinazolin-4(3H)-one acetic acid monosolvate.

In the title compound, C(8)H(3)ClN(4)O(5)·C(2)H(4)O(2), both the nitro groups are close to perpendicular [dihedral angles = 67.62 (15) and 86.73 (12)°] to the almost planar quinazoline unit [r.m.s. deviation = 0.014Å]. In the crystal, both the quinazoline and acetic acid mol-ecules form inversion dimers linked by pairs of N-H⋯O and O-H⋯O hydrogen bonds, respectively. R(2) (2)(8) loops arise in each case.

Related literature

For background to the biological properties of quinazoline derivatives, see: Pandeya et al. (1999 ▶); Tereshima et al. (1995 ▶); Wolfe et al. (1990 ▶). For a related structure, see: Srinivasan et al. (2011 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H3ClN4O5·C2H4O2

M = 330.65

Triclinic,

a = 7.3041 (12) Å

b = 9.3952 (16) Å

c = 9.6850 (16) Å

α = 83.813 (2)°

β = 88.172 (2)°

γ = 89.033 (2)°

V = 660.35 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.25 × 0.23 × 0.21 mm

Data collection

Rigaku SCXmini diffractometer

4758 measured reflections

2332 independent reflections

1810 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.123

S = 1.05

2332 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 datablock(s) I, global. DOI: 10.1107/S1600536811055735/hb6577sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811055735/hb6577Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055735/hb6577Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811055735/hb6577Isup4.cml

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

C8H3ClN4O5·C2H4O2	Z = 2
Mr = 330.65	F(000) = 336
Triclinic, P1	Dx = 1.663 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3041 (12) Å	Cell parameters from 30 reflections
b = 9.3952 (16) Å	θ = 3–25°
c = 9.6850 (16) Å	µ = 0.33 mm−1
α = 83.813 (2)°	T = 293 K
β = 88.172 (2)°	Block, yellow
γ = 89.033 (2)°	0.25 × 0.23 × 0.21 mm
V = 660.35 (19) Å3

Rigaku SCXmini diffractometer	Rint = 0.023
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 2.1°
graphite	h = −8→8
ω scans	k = −11→11
4758 measured reflections	l = −11→11
2332 independent reflections	3 standard reflections every 150 reflections
1810 reflections with I > 2σ(I)	intensity decay: none

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) = 0.123	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0589P)2 + 0.2567P] where P = (Fo2 + 2Fc2)/3
2332 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.32 e Å−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
Cl1	0.45451 (9)	0.28014 (8)	0.85154 (7)	0.0573 (3)
C1	−0.0819 (3)	0.4157 (2)	0.6577 (2)	0.0366 (5)
C2	0.0022 (3)	0.5048 (3)	0.7415 (3)	0.0410 (6)
H2	−0.0516	0.5922	0.7573	0.049*
C3	0.1646 (3)	0.4627 (3)	0.8006 (3)	0.0417 (6)
C4	0.2506 (3)	0.3322 (3)	0.7788 (2)	0.0406 (6)
C5	0.1668 (3)	0.2480 (2)	0.6936 (3)	0.0400 (6)
C6	−0.0007 (3)	0.2851 (2)	0.6312 (2)	0.0386 (6)
C7	−0.2288 (3)	0.2322 (3)	0.4948 (3)	0.0474 (6)
H7	−0.2823	0.1714	0.4385	0.057*
C8	−0.2573 (3)	0.4555 (3)	0.5944 (2)	0.0399 (6)
C9	0.6882 (5)	0.8879 (4)	0.7816 (4)	0.0864 (11)
H9A	0.7294	0.9190	0.6883	0.130*
H9B	0.5696	0.9291	0.7990	0.130*
H9C	0.6807	0.7854	0.7936	0.130*
C10	0.8197 (4)	0.9348 (3)	0.8806 (3)	0.0577 (7)
N1	0.2488 (3)	0.5589 (3)	0.8899 (3)	0.0516 (6)
N2	0.2536 (3)	0.1115 (2)	0.6652 (2)	0.0469 (5)
N3	−0.0740 (3)	0.1927 (2)	0.5468 (2)	0.0473 (5)
N4	−0.3205 (3)	0.3552 (2)	0.5155 (2)	0.0424 (5)
H4A	−0.4242	0.3712	0.4768	0.051*
O1	−0.3420 (2)	0.56686 (18)	0.6085 (2)	0.0546 (5)
O2	0.3030 (4)	0.6707 (3)	0.8373 (3)	0.0982 (9)
O3	0.2565 (4)	0.5191 (4)	1.0109 (3)	0.1116 (11)
O4	0.3643 (3)	0.1136 (2)	0.5693 (2)	0.0664 (6)
O5	0.2093 (3)	0.0052 (2)	0.7389 (2)	0.0735 (6)
O6	0.8157 (3)	1.0667 (2)	0.8998 (2)	0.0722 (6)
H100	0.9096	1.0894	0.9368	0.087*
O7	0.9282 (3)	0.8452 (2)	0.9401 (2)	0.0691 (6)

	U11	U22	U33	U12	U13	U23
Cl1	0.0381 (4)	0.0782 (5)	0.0559 (5)	0.0006 (3)	−0.0151 (3)	−0.0054 (3)
C1	0.0351 (12)	0.0392 (12)	0.0357 (13)	−0.0021 (10)	−0.0042 (10)	−0.0032 (10)
C2	0.0410 (14)	0.0386 (12)	0.0440 (14)	−0.0034 (10)	−0.0038 (11)	−0.0063 (10)
C3	0.0399 (13)	0.0480 (14)	0.0387 (13)	−0.0109 (11)	−0.0032 (11)	−0.0097 (11)
C4	0.0329 (13)	0.0504 (14)	0.0383 (13)	−0.0033 (11)	−0.0033 (11)	−0.0023 (11)
C5	0.0368 (13)	0.0403 (13)	0.0431 (14)	−0.0001 (10)	−0.0039 (11)	−0.0049 (11)
C6	0.0369 (13)	0.0394 (12)	0.0398 (13)	−0.0043 (10)	−0.0034 (11)	−0.0049 (10)
C7	0.0445 (15)	0.0473 (14)	0.0529 (16)	−0.0007 (12)	−0.0117 (13)	−0.0140 (12)
C8	0.0369 (13)	0.0418 (13)	0.0412 (14)	−0.0029 (11)	−0.0079 (11)	−0.0030 (11)
C9	0.092 (3)	0.080 (2)	0.090 (3)	−0.004 (2)	−0.037 (2)	−0.009 (2)
C10	0.0504 (17)	0.0579 (18)	0.0637 (19)	−0.0042 (14)	−0.0068 (14)	0.0007 (14)
N1	0.0443 (13)	0.0635 (15)	0.0504 (15)	−0.0095 (11)	−0.0075 (11)	−0.0179 (12)
N2	0.0406 (12)	0.0462 (13)	0.0546 (14)	0.0049 (10)	−0.0073 (11)	−0.0084 (11)
N3	0.0451 (12)	0.0459 (12)	0.0537 (13)	−0.0001 (10)	−0.0124 (10)	−0.0154 (10)
N4	0.0346 (11)	0.0472 (11)	0.0470 (12)	0.0002 (9)	−0.0135 (9)	−0.0090 (9)
O1	0.0483 (11)	0.0442 (10)	0.0745 (13)	0.0110 (8)	−0.0226 (10)	−0.0169 (9)
O2	0.132 (2)	0.0697 (15)	0.0967 (19)	−0.0419 (15)	−0.0373 (17)	−0.0089 (14)
O3	0.135 (3)	0.154 (3)	0.0519 (15)	−0.075 (2)	−0.0054 (16)	−0.0282 (16)
O4	0.0610 (13)	0.0697 (13)	0.0686 (14)	0.0091 (10)	0.0139 (11)	−0.0138 (11)
O5	0.0827 (16)	0.0466 (11)	0.0875 (16)	0.0069 (10)	0.0103 (13)	0.0048 (11)
O6	0.0634 (13)	0.0667 (14)	0.0885 (16)	0.0045 (10)	−0.0276 (12)	−0.0107 (12)
O7	0.0586 (12)	0.0571 (12)	0.0892 (16)	−0.0049 (10)	−0.0190 (12)	0.0094 (11)

Cl1—C4	1.710 (2)	C8—O1	1.225 (3)
C1—C2	1.390 (3)	C8—N4	1.371 (3)
C1—C6	1.399 (3)	C9—C10	1.482 (4)
C1—C8	1.463 (3)	C9—H9A	0.9600
C2—C3	1.368 (3)	C9—H9B	0.9600
C2—H2	0.9300	C9—H9C	0.9600
C3—C4	1.402 (3)	C10—O7	1.253 (4)
C3—N1	1.471 (3)	C10—O6	1.273 (3)
C4—C5	1.367 (3)	N1—O2	1.186 (3)
C5—C6	1.404 (3)	N1—O3	1.193 (3)
C5—N2	1.470 (3)	N2—O5	1.206 (3)
C6—N3	1.380 (3)	N2—O4	1.210 (3)
C7—N3	1.285 (3)	N4—H4A	0.8600
C7—N4	1.356 (3)	O6—H100	0.8254
C7—H7	0.9300
C2—C1—C6	120.8 (2)	O1—C8—C1	124.6 (2)
C2—C1—C8	121.1 (2)	N4—C8—C1	113.4 (2)
C6—C1—C8	118.0 (2)	C10—C9—H9A	109.5
C3—C2—C1	119.4 (2)	C10—C9—H9B	109.5
C3—C2—H2	120.3	H9A—C9—H9B	109.5
C1—C2—H2	120.3	C10—C9—H9C	109.5
C2—C3—C4	122.0 (2)	H9A—C9—H9C	109.5
C2—C3—N1	118.0 (2)	H9B—C9—H9C	109.5
C4—C3—N1	120.0 (2)	O7—C10—O6	123.4 (3)
C5—C4—C3	117.3 (2)	O7—C10—C9	119.6 (3)
C5—C4—Cl1	120.62 (19)	O6—C10—C9	117.0 (3)
C3—C4—Cl1	122.05 (19)	O2—N1—O3	124.5 (3)
C4—C5—C6	123.1 (2)	O2—N1—C3	117.9 (2)
C4—C5—N2	119.3 (2)	O3—N1—C3	117.5 (3)
C6—C5—N2	117.6 (2)	O5—N2—O4	124.6 (2)
N3—C6—C1	124.0 (2)	O5—N2—C5	117.7 (2)
N3—C6—C5	118.7 (2)	O4—N2—C5	117.7 (2)
C1—C6—C5	117.3 (2)	C7—N3—C6	115.4 (2)
N3—C7—N4	125.3 (2)	C7—N4—C8	123.8 (2)
N3—C7—H7	117.3	C7—N4—H4A	118.1
N4—C7—H7	117.3	C8—N4—H4A	118.1
O1—C8—N4	122.0 (2)	C10—O6—H100	111.3

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1i	0.86	1.97	2.827 (3)	173
O6—H100···O7ii	0.83	1.86	2.665 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1i	0.86	1.97	2.827 (3)	173
O6—H100⋯O7ii	0.83	1.86	2.665 (3)	163

Symmetry codes: (i) ; (ii) .