2-Anilino-3-(2-hy­droxy­phen­yl)quinazolin-4(3H)-one methanol monosolvate

Liu, B.; Chen, X.-B.; Yang, X.-H.; Pan, D.-F.; Ma, J.-K.

doi:10.1107/S1600536810030631

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages o2225-o2226

https://doi.org/10.1107/S1600536810030631

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2-Anilino-3-(2-hydroxyphenyl)quinazolin-4(3H)-one methanol monosolvate

Bi Liu,^a Xiao-Bao Chen,^b Xu-Hong Yang,^a ^* Dong-Feng Pan ^c and Jun-Kai Ma ^b

^aFaculty of Chemistry and Life Science, Xianning University, Xianning 437100, Hubei, People's Republic of China, ^bInstitute of Medicinal Chemistry, Hubei Medical University, Shiyan 442000, Hubei, People's Republic of China, and ^cDepartment of Oncology, Renmin Hospital, Hubei Medical University, Shiyan 442000, Hubei, People's Republic of China
^*Correspondence e-mail: chenxiaobao@yahoo.com.cn

(Received 27 July 2010; accepted 1 August 2010; online 11 August 2010)

In the title compound, C₂₀H₁₅N₃O₂·CH₃OH, the quinazolinone ring system is approximately planar, the dihedral angle between the pyrimidinone ring and the adjacent benzene ring being 1.73 (6)°. The pyrimidinone ring makes dihedral angles of 77.58 (6) and 29.62 (6)°, respectively, with the hydroxyphenyl and phenyl rings. In the crystal, the components are connected by O—H⋯O and C—H⋯O hydrogen bonds, forming a zigzag chain along the b axis.

Related literature

For the biological activity of quinazoline-4(3H)-one derivatives, see: Pandeya et al. (1999 ); Shiba et al. (1997 ); Malamas & Millen (1991 ); Mannschreck et al. (1984 ); Kung et al. (1999 ); Bartroli et al. (1998 ); Palmer et al. (1997 ); Tsou et al. (2001 ); Matsuno et al. (2002 ). For the synthesis of the title compound, see: Yang et al. (2008 ).

Experimental

Crystal data

C₂₀H₁₅N₃O₂·CH₄O
M_r = 361.39
Monoclinic, P 2₁ /c
a = 11.5575 (18) Å
b = 8.7305 (13) Å
c = 18.892 (3) Å
β = 106.251 (2)°
V = 1830.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.986, T_max = 0.991
21942 measured reflections
4541 independent reflections
3087 reflections with I > 2σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.123
S = 1.02
4541 reflections
254 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3ⁱ	0.940 (19)	1.74 (2)	2.6775 (14)	173.8 (17)
C11—H11⋯O1ⁱ	0.93	2.59	3.3781 (17)	143
O3—H3B⋯O1	0.90 (2)	1.85 (2)	2.7237 (14)	164.1 (18)
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810030631/is2582sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030631/is2582Isup2.hkl

checkCIF report

Comment top

Quinazoline-4(3H)-one derivatives have numerous biological properties. Some of these activities include antimicrobial (Pandeya et al., 1999; Shiba et al., 1997), antidiabetic (Malamas & Millen, 1991), anticonvulsant (Mannschreck et al., 1984), antibacterial (Kung et al., 1999), antifungal (Bartroli et al., 1998), protein tyrosine kinase inhibitors (Palmer et al., 1997), EGFR inhibitors (Tsou et al., 2001) and PDGFR phosphorylation inhibitors (Matsuno et al., 2002). We have recently focused on the synthesis of heterocyclic compounds using an aza-Wittig reaction. We present here the crystal structure of the title compound, (I) (Fig. 1), which can be used as a precursor for obtaining bioactive molecules.

In the crystal structure, the pyrimidinone heterocycle and the adjacent benzene ring are not planar, but inclined at 1.73 (6)°. Significant intermolecular O—H···O and C—H···O and intramolecular O—H···O contribute strongly to the stability of the molecular configuration (Table 1 and Fig. 2).

Related literature top

For the biological activity of quinazoline-4(3H)-one derivatives, see: Pandeya et al. (1999); Shiba et al. (1997); Malamas & Millen (1991); Mannschreck et al. (1984); Kung et al. (1999); Bartroli et al. (1998); Palmer et al. (1997); Tsou et al. (2001); Matsuno et al. (2002). For the synthesis of the title compound, see: Yang et al. (2008).

Experimental top

The title compound was prepared according to the literature method of Yang et al. (2008). To a solution of iminophosphorane (1.40 g, 3.0 mmol) in anhydrous THF (10 ml) was added isocyanatobenzene (3 mmol) under nitrogen at room temperature. After reaction, the mixture was allowed to stand for 10 h at 273–278 K, the solvent was removed under reduced pressure and diethyl ether/petroleum ether (1:2 v/v, 20 ml) was added to precipitate triphenylphosphine oxide. After filtration, the solvent was removed to give 1-phenyl- 3-(2-ethoxycarbonylphenyl) carbodiimide, which was used directly without further purification. To a solution of 1-phenyl- 3-(2-ethoxycarbonylphenyl) carbodiimide in THF (15 ml) was added 2-aminophenol (3 mmol). After the reaction mixture was allowed to stand for 0.5 h, the solvent was removed and anhydrous ethanol (10 ml) with several drops of EtONa in EtOH was added. The mixture was stirred for 2 h at room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give the title compound, (I). The product was recrystallized from methanol-dichloromethane (1:1 v/v, 20 ml) at room temperature to give crystals suitable for X-ray diffraction (yield 85%).

Structure description top

For the biological activity of quinazoline-4(3H)-one derivatives, see: Pandeya et al. (1999); Shiba et al. (1997); Malamas & Millen (1991); Mannschreck et al. (1984); Kung et al. (1999); Bartroli et al. (1998); Palmer et al. (1997); Tsou et al. (2001); Matsuno et al. (2002). For the synthesis of the title compound, see: Yang et al. (2008).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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. View of the molecular structure of (I), showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A partial packing view of the crystal packing of (I), showing the formation of O—H···O and C—H···O hydrogen-bonds as dashed lines.

2-Anilino-3-(2-hydroxyphenyl)quinazolin-4(3H)-one methanol monosolvate top

Crystal data top

C₂₀H₁₅N₃O₂·CH₄O	F(000) = 760
M_r = 361.39	D_x = 1.312 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6031 reflections
a = 11.5575 (18) Å	θ = 2.5–24.8°
b = 8.7305 (13) Å	µ = 0.09 mm⁻¹
c = 18.892 (3) Å	T = 298 K
β = 106.251 (2)°	Block, colorless
V = 1830.1 (5) Å³	0.16 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4541 independent reflections
Radiation source: fine-focus sealed tube	3087 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
φ and ω scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −15→15
T_min = 0.986, T_max = 0.991	k = −11→11
21942 measured reflections	l = −25→25

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0641P)²] where P = (F_o² + 2F_c²)/3
4541 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₀H₁₅N₃O₂·CH₄O	V = 1830.1 (5) Å³
M_r = 361.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5575 (18) Å	µ = 0.09 mm⁻¹
b = 8.7305 (13) Å	T = 298 K
c = 18.892 (3) Å	0.16 × 0.12 × 0.10 mm
β = 106.251 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4541 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3087 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.991	R_int = 0.074
21942 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.15 e Å⁻³
4541 reflections	Δρ_min = −0.20 e Å⁻³
254 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.14579 (11)	0.79335 (13)	0.16728 (6)	0.0498 (3)
C2	0.02576 (10)	0.74840 (13)	0.15172 (6)	0.0489 (3)
C3	−0.05802 (12)	0.85206 (15)	0.16547 (8)	0.0596 (3)
H3	−0.1387	0.8243	0.1554	0.072*
C4	−0.02146 (14)	0.99419 (16)	0.19373 (8)	0.0689 (4)
H4	−0.0774	1.0612	0.2037	0.083*
C5	0.09758 (14)	1.03937 (16)	0.20762 (8)	0.0704 (4)
H5	0.1208	1.1371	0.2257	0.085*
C6	0.18058 (12)	0.94065 (15)	0.19480 (7)	0.0631 (4)
H6	0.2606	0.9709	0.2043	0.076*
C7	0.23377 (10)	0.68658 (14)	0.15427 (7)	0.0502 (3)
C8	0.06580 (9)	0.51041 (13)	0.11378 (6)	0.0463 (3)
C9	0.27399 (9)	0.42459 (14)	0.12439 (6)	0.0476 (3)
C10	0.33853 (10)	0.35392 (14)	0.18934 (7)	0.0511 (3)
C11	0.41817 (10)	0.23803 (15)	0.18518 (8)	0.0579 (3)
H11	0.4634	0.1906	0.2281	0.070*
C12	0.43103 (10)	0.19237 (15)	0.11810 (8)	0.0610 (3)
H12	0.4834	0.1127	0.1160	0.073*
C13	0.36727 (12)	0.26327 (16)	0.05411 (8)	0.0636 (4)
H13	0.3767	0.2321	0.0090	0.076*
C14	0.28910 (11)	0.38117 (15)	0.05734 (7)	0.0578 (3)
H14	0.2468	0.4311	0.0144	0.069*
C15	−0.07866 (10)	0.29493 (13)	0.07155 (7)	0.0489 (3)
C16	−0.10077 (12)	0.17938 (15)	0.01980 (7)	0.0595 (3)
H16	−0.0431	0.1553	−0.0042	0.071*
C17	−0.20769 (13)	0.09931 (18)	0.00341 (8)	0.0753 (4)
H17	−0.2218	0.0210	−0.0313	0.090*
C18	−0.29321 (13)	0.1351 (2)	0.03829 (11)	0.0859 (5)
H18	−0.3660	0.0823	0.0269	0.103*
C19	−0.27106 (13)	0.24912 (18)	0.09009 (11)	0.0851 (5)
H19	−0.3291	0.2726	0.1140	0.102*
C20	−0.16407 (11)	0.32979 (16)	0.10748 (9)	0.0663 (4)
H20	−0.1498	0.4066	0.1430	0.080*
C21	0.58910 (15)	0.6035 (2)	0.12019 (10)	0.0872 (5)
H21A	0.6736	0.6041	0.1238	0.131*
H21B	0.5450	0.5624	0.0733	0.131*
H21C	0.5752	0.5414	0.1589	0.131*
N1	0.18861 (7)	0.54311 (10)	0.12879 (5)	0.0475 (2)
N2	−0.01409 (8)	0.60588 (11)	0.12228 (6)	0.0514 (3)
N3	0.03525 (9)	0.36584 (12)	0.08787 (6)	0.0559 (3)
H3A	0.0925 (13)	0.3156 (15)	0.0783 (8)	0.067*
O1	0.34102 (7)	0.71482 (11)	0.16472 (5)	0.0673 (3)
O2	0.31895 (9)	0.40317 (12)	0.25304 (5)	0.0712 (3)
H2A	0.3655 (16)	0.346 (2)	0.2930 (11)	0.107*
O3	0.54980 (9)	0.75565 (12)	0.12703 (6)	0.0731 (3)
H3B	0.4742 (18)	0.750 (2)	0.1312 (11)	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0534 (7)	0.0500 (7)	0.0447 (6)	−0.0022 (5)	0.0114 (5)	0.0037 (5)
C2	0.0520 (7)	0.0475 (7)	0.0478 (6)	0.0024 (5)	0.0149 (5)	0.0089 (5)
C3	0.0614 (8)	0.0534 (8)	0.0672 (8)	0.0088 (6)	0.0233 (6)	0.0111 (6)
C4	0.0882 (11)	0.0562 (8)	0.0676 (9)	0.0171 (7)	0.0304 (8)	0.0088 (7)
C5	0.0980 (12)	0.0502 (8)	0.0643 (9)	−0.0023 (7)	0.0246 (8)	−0.0033 (6)
C6	0.0712 (9)	0.0586 (8)	0.0580 (8)	−0.0113 (7)	0.0157 (6)	−0.0035 (6)
C7	0.0442 (6)	0.0549 (7)	0.0482 (7)	−0.0061 (5)	0.0074 (5)	0.0027 (5)
C8	0.0383 (6)	0.0494 (7)	0.0498 (6)	−0.0011 (5)	0.0098 (5)	0.0041 (5)
C9	0.0338 (5)	0.0531 (7)	0.0554 (7)	−0.0019 (5)	0.0121 (5)	0.0008 (5)
C10	0.0382 (6)	0.0602 (7)	0.0555 (7)	−0.0007 (5)	0.0140 (5)	0.0028 (6)
C11	0.0407 (6)	0.0634 (8)	0.0686 (8)	0.0039 (6)	0.0136 (6)	0.0073 (7)
C12	0.0448 (7)	0.0566 (8)	0.0860 (10)	−0.0001 (6)	0.0257 (7)	−0.0024 (7)
C13	0.0612 (8)	0.0689 (9)	0.0664 (9)	−0.0030 (7)	0.0270 (7)	−0.0102 (7)
C14	0.0512 (7)	0.0654 (8)	0.0562 (8)	−0.0004 (6)	0.0140 (6)	0.0022 (6)
C15	0.0389 (6)	0.0494 (7)	0.0553 (7)	−0.0023 (5)	0.0082 (5)	0.0037 (5)
C16	0.0588 (8)	0.0675 (8)	0.0519 (7)	−0.0093 (6)	0.0148 (6)	−0.0031 (6)
C17	0.0729 (10)	0.0792 (10)	0.0674 (9)	−0.0250 (8)	0.0090 (7)	−0.0155 (8)
C18	0.0508 (8)	0.0876 (12)	0.1150 (14)	−0.0237 (8)	0.0160 (9)	−0.0126 (10)
C19	0.0535 (8)	0.0737 (10)	0.1372 (16)	−0.0113 (7)	0.0414 (9)	−0.0175 (10)
C20	0.0490 (7)	0.0605 (8)	0.0927 (11)	−0.0064 (6)	0.0253 (7)	−0.0138 (7)
C21	0.0891 (11)	0.0905 (12)	0.0887 (12)	−0.0085 (9)	0.0360 (9)	−0.0110 (9)
N1	0.0362 (5)	0.0513 (6)	0.0531 (6)	0.0001 (4)	0.0095 (4)	0.0021 (4)
N2	0.0422 (5)	0.0489 (6)	0.0629 (6)	0.0026 (4)	0.0142 (4)	0.0034 (5)
N3	0.0384 (5)	0.0523 (6)	0.0776 (7)	−0.0009 (4)	0.0173 (5)	−0.0092 (5)
O1	0.0433 (5)	0.0739 (6)	0.0811 (7)	−0.0113 (4)	0.0114 (4)	−0.0051 (5)
O2	0.0689 (6)	0.0885 (7)	0.0568 (6)	0.0236 (5)	0.0184 (5)	0.0081 (5)
O3	0.0584 (6)	0.0883 (8)	0.0715 (6)	−0.0126 (5)	0.0163 (5)	−0.0109 (5)

Geometric parameters (Å, º) top

C1—C2	1.3917 (16)	C12—C13	1.3743 (19)
C1—C6	1.4031 (18)	C12—H12	0.9300
C1—C7	1.4502 (17)	C13—C14	1.3822 (18)
C2—N2	1.3879 (15)	C13—H13	0.9300
C2—C3	1.4017 (16)	C14—H14	0.9300
C3—C4	1.3701 (19)	C15—C16	1.3781 (17)
C3—H3	0.9300	C15—C20	1.3796 (17)
C4—C5	1.3840 (19)	C15—N3	1.4086 (14)
C4—H4	0.9300	C16—C17	1.3775 (18)
C5—C6	1.3608 (19)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.369 (2)
C6—H6	0.9300	C17—H17	0.9300
C7—O1	1.2244 (13)	C18—C19	1.369 (2)
C7—N1	1.3901 (15)	C18—H18	0.9300
C8—N2	1.2869 (14)	C19—C20	1.3804 (18)
C8—N3	1.3640 (15)	C19—H19	0.9300
C8—N1	1.3969 (13)	C20—H20	0.9300
C9—C14	1.3793 (17)	C21—O3	1.4210 (19)
C9—C10	1.3893 (17)	C21—H21A	0.9600
C9—N1	1.4482 (14)	C21—H21B	0.9600
C10—O2	1.3554 (16)	C21—H21C	0.9600
C10—C11	1.3848 (16)	N3—H3A	0.854 (14)
C11—C12	1.3755 (19)	O2—H2A	0.940 (19)
C11—H11	0.9300	O3—H3B	0.90 (2)

C2—C1—C6	120.14 (11)	C14—C13—H13	120.2
C2—C1—C7	119.19 (11)	C9—C14—C13	119.83 (12)
C6—C1—C7	120.67 (11)	C9—C14—H14	120.1
N2—C2—C1	122.47 (11)	C13—C14—H14	120.1
N2—C2—C3	118.96 (11)	C16—C15—C20	119.63 (11)
C1—C2—C3	118.57 (11)	C16—C15—N3	116.96 (11)
C4—C3—C2	120.22 (13)	C20—C15—N3	123.30 (11)
C4—C3—H3	119.9	C17—C16—C15	120.50 (13)
C2—C3—H3	119.9	C17—C16—H16	119.8
C3—C4—C5	120.92 (13)	C15—C16—H16	119.8
C3—C4—H4	119.5	C18—C17—C16	119.95 (14)
C5—C4—H4	119.5	C18—C17—H17	120.0
C6—C5—C4	119.91 (13)	C16—C17—H17	120.0
C6—C5—H5	120.0	C17—C18—C19	119.64 (13)
C4—C5—H5	120.0	C17—C18—H18	120.2
C5—C6—C1	120.22 (12)	C19—C18—H18	120.2
C5—C6—H6	119.9	C18—C19—C20	121.13 (14)
C1—C6—H6	119.9	C18—C19—H19	119.4
O1—C7—N1	120.15 (11)	C20—C19—H19	119.4
O1—C7—C1	124.71 (11)	C15—C20—C19	119.14 (13)
N1—C7—C1	115.14 (10)	C15—C20—H20	120.4
N2—C8—N3	121.42 (10)	C19—C20—H20	120.4
N2—C8—N1	124.48 (11)	O3—C21—H21A	109.5
N3—C8—N1	114.10 (10)	O3—C21—H21B	109.5
C14—C9—C10	120.95 (11)	H21A—C21—H21B	109.5
C14—C9—N1	120.83 (10)	O3—C21—H21C	109.5
C10—C9—N1	118.20 (10)	H21A—C21—H21C	109.5
O2—C10—C11	124.12 (11)	H21B—C21—H21C	109.5
O2—C10—C9	117.49 (11)	C7—N1—C8	121.07 (10)
C11—C10—C9	118.39 (12)	C7—N1—C9	117.90 (9)
C12—C11—C10	120.59 (12)	C8—N1—C9	120.82 (9)
C12—C11—H11	119.7	C8—N2—C2	117.48 (10)
C10—C11—H11	119.7	C8—N3—C15	128.13 (10)
C13—C12—C11	120.68 (12)	C8—N3—H3A	114.4 (9)
C13—C12—H12	119.7	C15—N3—H3A	117.4 (9)
C11—C12—H12	119.7	C10—O2—H2A	110.0 (11)
C12—C13—C14	119.52 (13)	C21—O3—H3B	107.3 (12)
C12—C13—H13	120.2

C6—C1—C2—N2	177.94 (11)	N3—C15—C16—C17	176.81 (12)
C7—C1—C2—N2	−1.67 (17)	C15—C16—C17—C18	0.5 (2)
C6—C1—C2—C3	−1.20 (17)	C16—C17—C18—C19	−0.9 (3)
C7—C1—C2—C3	179.18 (11)	C17—C18—C19—C20	0.5 (3)
N2—C2—C3—C4	−179.27 (11)	C16—C15—C20—C19	−0.8 (2)
C1—C2—C3—C4	−0.10 (18)	N3—C15—C20—C19	−176.97 (13)
C2—C3—C4—C5	1.5 (2)	C18—C19—C20—C15	0.4 (3)
C3—C4—C5—C6	−1.6 (2)	O1—C7—N1—C8	−177.48 (10)
C4—C5—C6—C1	0.2 (2)	C1—C7—N1—C8	3.11 (16)
C2—C1—C6—C5	1.14 (18)	O1—C7—N1—C9	7.77 (16)
C7—C1—C6—C5	−179.25 (12)	C1—C7—N1—C9	−171.63 (9)
C2—C1—C7—O1	178.64 (11)	N2—C8—N1—C7	−0.53 (17)
C6—C1—C7—O1	−0.98 (18)	N3—C8—N1—C7	178.81 (10)
C2—C1—C7—N1	−1.99 (16)	N2—C8—N1—C9	174.06 (11)
C6—C1—C7—N1	178.40 (10)	N3—C8—N1—C9	−6.60 (15)
C14—C9—C10—O2	179.84 (11)	C14—C9—N1—C7	−104.81 (13)
N1—C9—C10—O2	−1.35 (16)	C10—C9—N1—C7	76.38 (13)
C14—C9—C10—C11	−0.32 (17)	C14—C9—N1—C8	80.43 (13)
N1—C9—C10—C11	178.49 (10)	C10—C9—N1—C8	−98.38 (13)
O2—C10—C11—C12	178.59 (12)	N3—C8—N2—C2	177.48 (11)
C9—C10—C11—C12	−1.24 (17)	N1—C8—N2—C2	−3.23 (17)
C10—C11—C12—C13	1.56 (19)	C1—C2—N2—C8	4.31 (16)
C11—C12—C13—C14	−0.29 (19)	C3—C2—N2—C8	−176.55 (10)
C10—C9—C14—C13	1.57 (18)	N2—C8—N3—C15	−4.5 (2)
N1—C9—C14—C13	−177.21 (11)	N1—C8—N3—C15	176.17 (11)
C12—C13—C14—C9	−1.26 (19)	C16—C15—N3—C8	153.97 (13)
C20—C15—C16—C17	0.4 (2)	C20—C15—N3—C8	−29.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3ⁱ	0.940 (19)	1.74 (2)	2.6775 (14)	173.8 (17)
C11—H11···O1ⁱ	0.93	2.59	3.3781 (17)	143
O3—H3B···O1	0.90 (2)	1.85 (2)	2.7237 (14)	164.1 (18)

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅N₃O₂·CH₄O
M_r	361.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.5575 (18), 8.7305 (13), 18.892 (3)
β (°)	106.251 (2)
V (Å³)	1830.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.986, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	21942, 4541, 3087
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.123, 1.02
No. of reflections	4541
No. of parameters	254
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.20

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), 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
O2—H2A···O3ⁱ	0.940 (19)	1.74 (2)	2.6775 (14)	173.8 (17)
C11—H11···O1ⁱ	0.93	2.59	3.3781 (17)	143.2
O3—H3B···O1	0.90 (2)	1.85 (2)	2.7237 (14)	164.1 (18)

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Acknowledgements

The authors are grateful to the Hubei Medical University Educational Committee (grant No. 2009QJ12) for financial support, and acknowledge the Sophisticated Analytical Instrument Facility, Central China Normal University, Wuhan, for the data collection.

References

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