4-(4-Amino-2-fluoro-phen-oxy)-7-meth-oxy-quinazolin-6-ol methanol monosolvate.

In the title compound, C(15)H(12)FN(3)O(3)·CH(3)OH, the dihedral angle between the quinazoline ring system and the benzene ring is 81.18 (9)°. In the crystal, mol-ecules are linked by N-H⋯O and O-H⋯N hydrogen bonds, generating [10-1] chains of alternating main mol-ecules and solvent mol-ecules. Weak C-H⋯O inter-actions are also observed.

Related literature

For background to quinazolinones, see: Priya et al. (2011 ▶). For further synthetic details, see: Furuta et al. (2006 ▶).

Experimental

Crystal data

C15H12FN3O3·CH4O

M = 333.32

Triclinic,

a = 8.723 (2) Å

b = 8.921 (2) Å

c = 11.500 (3) Å

α = 70.925 (4)°

β = 69.940 (4)°

γ = 77.273 (4)°

V = 788.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART 4K CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.974, T max = 0.989

4819 measured reflections

2747 independent reflections

2010 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.085

wR(F 2) = 0.193

S = 1.17

2747 reflections

227 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011725/hb6683sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011725/hb6683Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011725/hb6683Isup3.cml

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

C15H12FN3O3·CH4O	Z = 2
Mr = 333.32	F(000) = 348
Triclinic, P1	Dx = 1.404 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.723 (2) Å	Cell parameters from 2516 reflections
b = 8.921 (2) Å	θ = 2.6–25.3°
c = 11.500 (3) Å	µ = 0.11 mm−1
α = 70.925 (4)°	T = 298 K
β = 69.940 (4)°	Block, colorless
γ = 77.273 (4)°	0.15 × 0.12 × 0.10 mm
V = 788.6 (3) Å3

Bruker SMART 4K CCD diffractometer	2747 independent reflections
Radiation source: fine-focus sealed tube	2010 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→7
Tmin = 0.974, Tmax = 0.989	k = −10→10
4819 measured reflections	l = −13→13

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)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.067P)2 + 0.5658P] where P = (Fo2 + 2Fc2)/3
2747 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.22 e Å−3
2 restraints	Δρmin = −0.31 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
C1	0.0141 (7)	−0.2778 (6)	0.8438 (4)	0.0716 (14)
H1A	0.1224	−0.2790	0.8480	0.107*
H1B	−0.0365	−0.3654	0.9105	0.107*
H1C	−0.0510	−0.1790	0.8554	0.107*
C2	0.1142 (4)	−0.1900 (4)	0.6163 (3)	0.0403 (9)
C3	0.1429 (4)	−0.2237 (4)	0.4980 (3)	0.0388 (9)
C4	0.2366 (4)	−0.1341 (4)	0.3861 (3)	0.0394 (9)
H4	0.2569	−0.1582	0.3089	0.047*
C5	0.3027 (4)	−0.0040 (4)	0.3884 (3)	0.0365 (8)
C6	0.2702 (4)	0.0325 (4)	0.5041 (3)	0.0378 (8)
C7	0.1759 (5)	−0.0628 (4)	0.6196 (4)	0.0438 (9)
H7	0.1556	−0.0400	0.6973	0.053*
C8	0.4216 (5)	0.2396 (4)	0.4001 (4)	0.0524 (11)
H8	0.4621	0.3259	0.4030	0.063*
C9	0.4066 (5)	0.0943 (4)	0.2791 (3)	0.0401 (9)
C10	0.5608 (5)	0.1413 (4)	0.0612 (3)	0.0424 (9)
C11	0.5111 (5)	0.2878 (5)	−0.0120 (4)	0.0482 (10)
C12	0.6172 (6)	0.3746 (4)	−0.1182 (4)	0.0497 (10)
H12	0.5798	0.4740	−0.1652	0.060*
C13	0.7798 (5)	0.3131 (4)	−0.1545 (3)	0.0424 (9)
C14	0.8321 (5)	0.1640 (4)	−0.0821 (4)	0.0485 (10)
H14	0.9418	0.1211	−0.1057	0.058*
C15	0.7208 (5)	0.0794 (4)	0.0251 (4)	0.0498 (10)
H15	0.7563	−0.0205	0.0725	0.060*
C16	0.3354 (6)	0.3722 (7)	0.7115 (6)	0.0910 (18)
H16A	0.3020	0.4117	0.7859	0.136*
H16B	0.3274	0.4594	0.6373	0.136*
H16C	0.4471	0.3223	0.6983	0.136*
O1	0.0249 (3)	−0.2927 (3)	0.7224 (2)	0.0518 (7)
O2	0.0736 (4)	−0.3501 (3)	0.5054 (2)	0.0569 (8)
H2	0.0888	−0.3564	0.4326	0.085*
O3	0.4459 (3)	0.0561 (3)	0.1677 (2)	0.0536 (8)
N1	0.3312 (4)	0.1598 (3)	0.5098 (3)	0.0499 (9)
N2	0.4647 (4)	0.2147 (3)	0.2832 (3)	0.0479 (8)
F1	0.3505 (3)	0.3488 (3)	0.0233 (3)	0.0773 (8)
N3	0.8919 (5)	0.3961 (4)	−0.2678 (3)	0.0548 (10)
H3A	0.864 (6)	0.496 (3)	−0.282 (5)	0.082*
H3B	0.991 (3)	0.355 (5)	−0.261 (4)	0.066*
O5	0.2333 (4)	0.2605 (4)	0.7305 (3)	0.0699 (9)
H5	0.2582	0.2309	0.6653	0.105*

	U11	U22	U33	U12	U13	U23
C1	0.101 (4)	0.068 (3)	0.035 (2)	−0.042 (3)	0.003 (2)	−0.002 (2)
C2	0.043 (2)	0.0290 (18)	0.041 (2)	−0.0122 (16)	−0.0065 (17)	−0.0001 (16)
C3	0.046 (2)	0.0293 (17)	0.042 (2)	−0.0159 (16)	−0.0149 (17)	−0.0015 (15)
C4	0.047 (2)	0.0310 (18)	0.041 (2)	−0.0167 (16)	−0.0129 (17)	−0.0031 (16)
C5	0.039 (2)	0.0284 (17)	0.040 (2)	−0.0107 (15)	−0.0104 (16)	−0.0033 (15)
C6	0.044 (2)	0.0274 (17)	0.043 (2)	−0.0109 (15)	−0.0117 (17)	−0.0071 (16)
C7	0.050 (2)	0.038 (2)	0.040 (2)	−0.0116 (17)	−0.0039 (18)	−0.0127 (17)
C8	0.074 (3)	0.039 (2)	0.052 (3)	−0.030 (2)	−0.017 (2)	−0.0094 (19)
C9	0.049 (2)	0.0317 (18)	0.039 (2)	−0.0157 (16)	−0.0127 (17)	−0.0012 (15)
C10	0.057 (3)	0.038 (2)	0.033 (2)	−0.0257 (19)	−0.0084 (18)	−0.0030 (16)
C11	0.050 (3)	0.049 (2)	0.046 (2)	−0.014 (2)	−0.0107 (19)	−0.0125 (19)
C12	0.071 (3)	0.0332 (19)	0.045 (2)	−0.021 (2)	−0.019 (2)	0.0018 (17)
C13	0.063 (3)	0.0354 (19)	0.034 (2)	−0.0293 (19)	−0.0111 (19)	−0.0042 (16)
C14	0.057 (3)	0.044 (2)	0.044 (2)	−0.0181 (19)	−0.0113 (19)	−0.0076 (18)
C15	0.063 (3)	0.036 (2)	0.043 (2)	−0.0171 (19)	−0.014 (2)	0.0046 (17)
C16	0.074 (4)	0.095 (4)	0.140 (5)	−0.002 (3)	−0.049 (4)	−0.065 (4)
O1	0.0629 (18)	0.0458 (15)	0.0390 (15)	−0.0292 (13)	−0.0019 (13)	−0.0005 (12)
O2	0.086 (2)	0.0451 (15)	0.0448 (16)	−0.0451 (15)	−0.0136 (16)	−0.0002 (13)
O3	0.075 (2)	0.0495 (15)	0.0355 (14)	−0.0423 (14)	−0.0008 (13)	−0.0039 (12)
N1	0.064 (2)	0.0368 (17)	0.051 (2)	−0.0236 (16)	−0.0090 (17)	−0.0105 (15)
N2	0.064 (2)	0.0373 (17)	0.0438 (19)	−0.0303 (16)	−0.0088 (16)	−0.0040 (14)
F1	0.0647 (18)	0.0707 (17)	0.0825 (19)	−0.0111 (13)	−0.0131 (15)	−0.0101 (14)
N3	0.075 (3)	0.048 (2)	0.0408 (19)	−0.037 (2)	−0.0098 (19)	0.0006 (17)
O5	0.096 (2)	0.0598 (18)	0.0517 (18)	−0.0249 (18)	−0.0110 (17)	−0.0134 (15)

C1—O1	1.416 (5)	C10—C15	1.356 (5)
C1—H1A	0.9600	C10—C11	1.373 (5)
C1—H1B	0.9600	C10—O3	1.403 (4)
C1—H1C	0.9600	C11—F1	1.357 (5)
C2—O1	1.366 (4)	C11—C12	1.368 (5)
C2—C7	1.375 (5)	C12—C13	1.374 (6)
C2—C3	1.415 (5)	C12—H12	0.9300
C3—O2	1.360 (4)	C13—C14	1.393 (5)
C3—C4	1.363 (5)	C13—N3	1.420 (5)
C4—C5	1.416 (4)	C14—C15	1.388 (5)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.393 (5)	C15—H15	0.9300
C5—C9	1.421 (5)	C16—O5	1.396 (5)
C6—N1	1.385 (4)	C16—H16A	0.9600
C6—C7	1.409 (5)	C16—H16B	0.9600
C7—H7	0.9300	C16—H16C	0.9600
C8—N1	1.303 (5)	O2—H2	0.8200
C8—N2	1.346 (5)	N3—H3A	0.848 (19)
C8—H8	0.9300	N3—H3B	0.879 (19)
C9—N2	1.304 (4)	O5—H5	0.8200
C9—O3	1.344 (4)
O1—C1—H1A	109.5	C11—C10—O3	120.1 (4)
O1—C1—H1B	109.5	F1—C11—C12	118.9 (4)
H1A—C1—H1B	109.5	F1—C11—C10	118.6 (3)
O1—C1—H1C	109.5	C12—C11—C10	122.5 (4)
H1A—C1—H1C	109.5	C11—C12—C13	119.1 (4)
H1B—C1—H1C	109.5	C11—C12—H12	120.4
O1—C2—C7	124.3 (3)	C13—C12—H12	120.4
O1—C2—C3	115.2 (3)	C12—C13—C14	119.1 (3)
C7—C2—C3	120.5 (3)	C12—C13—N3	120.7 (4)
O2—C3—C4	123.6 (3)	C14—C13—N3	120.1 (4)
O2—C3—C2	115.6 (3)	C15—C14—C13	120.1 (4)
C4—C3—C2	120.7 (3)	C15—C14—H14	119.9
C3—C4—C5	119.4 (3)	C13—C14—H14	119.9
C3—C4—H4	120.3	C10—C15—C14	120.5 (4)
C5—C4—H4	120.3	C10—C15—H15	119.7
C6—C5—C4	120.0 (3)	C14—C15—H15	119.7
C6—C5—C9	115.4 (3)	O5—C16—H16A	109.5
C4—C5—C9	124.6 (3)	O5—C16—H16B	109.5
N1—C6—C5	121.7 (3)	H16A—C16—H16B	109.5
N1—C6—C7	118.2 (3)	O5—C16—H16C	109.5
C5—C6—C7	120.1 (3)	H16A—C16—H16C	109.5
C2—C7—C6	119.2 (3)	H16B—C16—H16C	109.5
C2—C7—H7	120.4	C2—O1—C1	116.9 (3)
C6—C7—H7	120.4	C3—O2—H2	109.5
N1—C8—N2	129.2 (3)	C9—O3—C10	117.4 (3)
N1—C8—H8	115.4	C8—N1—C6	114.9 (3)
N2—C8—H8	115.4	C9—N2—C8	115.3 (3)
N2—C9—O3	120.2 (3)	C13—N3—H3A	111 (3)
N2—C9—C5	123.5 (3)	C13—N3—H3B	106 (3)
O3—C9—C5	116.3 (3)	H3A—N3—H3B	119 (5)
C15—C10—C11	118.6 (3)	C16—O5—H5	109.5
C15—C10—O3	121.3 (3)
O1—C2—C3—O2	2.0 (5)	O3—C10—C11—C12	−178.7 (3)
C7—C2—C3—O2	−178.7 (3)	F1—C11—C12—C13	−179.8 (3)
O1—C2—C3—C4	−177.1 (3)	C10—C11—C12—C13	0.6 (6)
C7—C2—C3—C4	2.2 (5)	C11—C12—C13—C14	0.0 (5)
O2—C3—C4—C5	179.7 (3)	C11—C12—C13—N3	176.8 (3)
C2—C3—C4—C5	−1.3 (5)	C12—C13—C14—C15	0.0 (5)
C3—C4—C5—C6	−0.8 (5)	N3—C13—C14—C15	−176.9 (3)
C3—C4—C5—C9	177.7 (4)	C11—C10—C15—C14	1.2 (6)
C4—C5—C6—N1	−179.3 (3)	O3—C10—C15—C14	178.6 (3)
C9—C5—C6—N1	2.1 (5)	C13—C14—C15—C10	−0.6 (6)
C4—C5—C6—C7	2.0 (5)	C7—C2—O1—C1	−8.3 (6)
C9—C5—C6—C7	−176.5 (3)	C3—C2—O1—C1	170.9 (4)
O1—C2—C7—C6	178.3 (3)	N2—C9—O3—C10	5.3 (5)
C3—C2—C7—C6	−0.9 (5)	C5—C9—O3—C10	−174.0 (3)
N1—C6—C7—C2	−179.9 (3)	C15—C10—O3—C9	99.6 (4)
C5—C6—C7—C2	−1.2 (5)	C11—C10—O3—C9	−83.0 (4)
C6—C5—C9—N2	−2.3 (5)	N2—C8—N1—C6	−0.7 (7)
C4—C5—C9—N2	179.2 (4)	C5—C6—N1—C8	−0.8 (5)
C6—C5—C9—O3	176.9 (3)	C7—C6—N1—C8	177.9 (4)
C4—C5—C9—O3	−1.6 (5)	O3—C9—N2—C8	−178.1 (4)
C15—C10—C11—F1	179.2 (3)	C5—C9—N2—C8	1.0 (6)
O3—C10—C11—F1	1.7 (5)	N1—C8—N2—C9	0.5 (7)
C15—C10—C11—C12	−1.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N3i	0.82	1.98	2.799 (4)	172
N3—H3A···O1ii	0.85 (2)	2.60 (4)	3.192 (4)	128 (4)
N3—H3B···O5iii	0.88 (2)	2.08 (2)	2.953 (6)	173 (4)
O5—H5···N1	0.82	1.95	2.765 (4)	177
C15—H15···O5iv	0.93	2.57	3.453 (5)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N3i	0.82	1.98	2.799 (4)	172
N3—H3A⋯O1ii	0.85 (2)	2.60 (4)	3.192 (4)	128 (4)
N3—H3B⋯O5iii	0.88 (2)	2.08 (2)	2.953 (6)	173 (4)
O5—H5⋯N1	0.82	1.95	2.765 (4)	177
C15—H15⋯O5iv	0.93	2.57	3.453 (5)	159

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .