2-[2-(2-Anilino-4-oxo-3,4-dihydro­quinazolin-3-yl)phen­oxy]-3-phenyl­quinazolin-4(3H)-one methanol hemisolvate

Gao, T.; Chen, X.-B.; Yang, X.-H.; Wang, X.

doi:10.1107/S1600536810028011

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Pages o2075-o2076

https://doi.org/10.1107/S1600536810028011

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2-[2-(2-Anilino-4-oxo-3,4-dihydroquinazolin-3-yl)phenoxy]-3-phenylquinazolin-4(3H)-one methanol hemisolvate

Tao Gao,^a Xiao-Bao Chen,^b Xu-Hong Yang ^a ^* and Xiang Wang ^c

^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 ^cCollege of Life and Environmental Science, Kaili University, Kaili 556000, Guizhou, People's Republic of China
^*Correspondence e-mail: chenxiaobao@yahoo.com.cn

(Received 6 July 2010; accepted 14 July 2010; online 21 July 2010)

In the title compound, C₃₄H₂₃N₅O₃·0.5CH₃OH, each pyrimidinone heterocycle and its adjacent benzene ring are almost coplanar, making dihedral angles of 0.69 (13) and 1.87 (13)°. The lower pyrimidinone ring makes a dihedral angle of 40.41 (15)° with the —NH— bonded phenyl ring. O—H⋯O hydrogen bonds and weak C—H⋯π interactions are observed in the crystal structure. The methanol solvent molecule is disordered over two positions of equal occupancy.

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

C₃₄H₂₃N₅O₃·0.5CH₄O
M_r = 565.60
Monoclinic, C 2/c
a = 24.268 (2) Å
b = 16.5049 (14) Å
c = 15.2929 (12) Å
β = 110.382 (1)°
V = 5741.9 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 292 K
0.32 × 0.25 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.963, T_max = 0.979
16455 measured reflections
5631 independent reflections
3943 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.228
S = 1.04
5631 reflections
397 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C29–C34 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H35⋯O5ⁱ	0.96	0.96	1.711 (7)	125
C2—H2⋯Cg1ⁱⁱ	0.93	2.75	3.617 (3)	155
Symmetry codes: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ .

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/S1600536810028011/bq2224sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810028011/bq2224Isup2.hkl

checkCIF report

Comment top

Quinazoline-4(3H)-one derivatives have numerous biological properties. Some of these activities include antimicrobial (Pandeya et al., 1999 and 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 almost planar and inclined at 0.69 (13) ° and 1.87 (13) °. The crystal structure (Fig. 2) is stabilized by weak intermolecular C—H···π hydrogen bonds (Table 1).

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

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 (1.5 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. The product was recrystallized from methanol-dichloromethane (1:2 v/v, 20 ml) at room temperature to give crystals suitable for X-ray diffraction (yield 74%).

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 schemeand with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A partial view of the crystal packing of (I). Dashed lines show C-H···π interaction.

2-[2-(2-Anilino-4-oxo-3,4-dihydroquinazolin-3-yl)phenoxy]-3- phenylquinazolin-4(3H)-one methanol hemisolvate top

Crystal data top

C₃₄H₂₃N₅O₃·0.5CH₄O	F(000) = 2360
M_r = 565.60	D_x = 1.309 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3884 reflections
a = 24.268 (2) Å	θ = 2.5–23.6°
b = 16.5049 (14) Å	µ = 0.09 mm⁻¹
c = 15.2929 (12) Å	T = 292 K
β = 110.382 (1)°	Block, colorless
V = 5741.9 (8) Å³	0.32 × 0.25 × 0.24 mm
Z = 8

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5631 independent reflections
Radiation source: fine-focus sealed tube	3943 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −29→23
T_min = 0.963, T_max = 0.979	k = −20→20
16455 measured reflections	l = −18→18

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.228	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1434P)² + 2.1314P] where P = (F_o² + 2F_c²)/3
5631 reflections	(Δ/σ)_max = 0.002
397 parameters	Δρ_max = 0.78 e Å⁻³
12 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₃₄H₂₃N₅O₃·0.5CH₄O	V = 5741.9 (8) Å³
M_r = 565.60	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.268 (2) Å	µ = 0.09 mm⁻¹
b = 16.5049 (14) Å	T = 292 K
c = 15.2929 (12) Å	0.32 × 0.25 × 0.24 mm
β = 110.382 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5631 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3943 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.979	R_int = 0.022
16455 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	12 restraints
wR(F²) = 0.228	H-atom parameters constrained
S = 1.04	Δρ_max = 0.78 e Å⁻³
5631 reflections	Δρ_min = −0.26 e Å⁻³
397 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	Occ. (<1)
C1	0.33889 (11)	0.39224 (16)	0.95966 (18)	0.0574 (6)
H1	0.2986	0.3843	0.9429	0.069*
C2	0.37488 (14)	0.3822 (2)	1.0508 (2)	0.0749 (8)
H2	0.3587	0.3681	1.0956	0.090*
C3	0.43447 (15)	0.3929 (3)	1.0766 (2)	0.0890 (10)
H3	0.4586	0.3857	1.1384	0.107*
C4	0.45792 (13)	0.4139 (3)	1.0111 (2)	0.0921 (11)
H4	0.4983	0.4211	1.0284	0.110*
C5	0.42214 (12)	0.4248 (2)	0.9184 (2)	0.0709 (8)
H5	0.4385	0.4392	0.8739	0.085*
C6	0.36227 (10)	0.41392 (14)	0.89331 (17)	0.0478 (5)
C7	0.27029 (10)	0.43844 (13)	0.76026 (15)	0.0444 (5)
C8	0.18242 (10)	0.43060 (15)	0.62005 (16)	0.0491 (6)
C9	0.15259 (10)	0.46910 (14)	0.67699 (16)	0.0477 (5)
C10	0.09255 (11)	0.48514 (16)	0.6402 (2)	0.0600 (7)
H10	0.0712	0.4718	0.5786	0.072*
C11	0.06483 (12)	0.52059 (18)	0.6949 (2)	0.0688 (8)
H11	0.0247	0.5314	0.6704	0.083*
C12	0.09658 (13)	0.54019 (18)	0.7862 (2)	0.0689 (8)
H12	0.0775	0.5642	0.8229	0.083*
C13	0.15578 (12)	0.52491 (15)	0.8240 (2)	0.0587 (6)
H13	0.1766	0.5388	0.8857	0.070*
C14	0.18475 (10)	0.48859 (13)	0.76995 (16)	0.0458 (5)
C15	0.27546 (10)	0.37942 (14)	0.61502 (15)	0.0458 (5)
C16	0.29309 (12)	0.42318 (16)	0.55277 (17)	0.0565 (6)
H16	0.2841	0.4780	0.5433	0.068*
C17	0.32434 (13)	0.38468 (18)	0.50451 (19)	0.0642 (7)
H17	0.3371	0.4140	0.4632	0.077*
C18	0.33669 (12)	0.30324 (18)	0.51737 (18)	0.0614 (7)
H18	0.3570	0.2777	0.4836	0.074*
C19	0.31914 (11)	0.25893 (16)	0.58009 (17)	0.0535 (6)
H19	0.3279	0.2040	0.5893	0.064*
C20	0.28861 (10)	0.29777 (14)	0.62827 (15)	0.0457 (5)
C21	0.30048 (10)	0.22726 (13)	0.76894 (16)	0.0457 (5)
C22	0.38728 (11)	0.19895 (14)	0.88305 (17)	0.0527 (6)
C23	0.44826 (12)	0.20351 (18)	0.9158 (2)	0.0678 (7)
H23	0.4675	0.2278	0.8796	0.081*
C24	0.48029 (14)	0.1718 (2)	1.0022 (2)	0.0782 (9)
H24	0.5211	0.1757	1.0244	0.094*
C25	0.45238 (15)	0.1344 (2)	1.0559 (2)	0.0796 (9)
H25	0.4743	0.1129	1.1138	0.096*
C26	0.39234 (14)	0.12903 (18)	1.0239 (2)	0.0698 (8)
H26	0.3735	0.1033	1.0598	0.084*
C27	0.35942 (12)	0.16190 (15)	0.93765 (17)	0.0547 (6)
C28	0.29550 (12)	0.15817 (16)	0.90513 (18)	0.0570 (6)
C29	0.20409 (10)	0.20150 (14)	0.78235 (16)	0.0465 (5)
C30	0.17127 (12)	0.13978 (17)	0.72933 (18)	0.0598 (7)
H30	0.1896	0.0934	0.7182	0.072*
C31	0.11087 (13)	0.1470 (2)	0.6926 (2)	0.0734 (8)
H31	0.0884	0.1054	0.6564	0.088*
C32	0.08382 (12)	0.2155 (2)	0.7093 (2)	0.0707 (8)
H32	0.0431	0.2203	0.6843	0.085*
C33	0.11721 (13)	0.27667 (19)	0.7630 (2)	0.0713 (8)
H33	0.0990	0.3230	0.7744	0.086*
C34	0.17759 (12)	0.26988 (16)	0.8003 (2)	0.0615 (7)
H34	0.2001	0.3111	0.8372	0.074*
N1	0.32858 (9)	0.42035 (13)	0.79688 (14)	0.0520 (5)
N2	0.24407 (8)	0.47305 (12)	0.81070 (13)	0.0486 (5)
N3	0.24277 (8)	0.41832 (11)	0.66622 (13)	0.0461 (5)
N4	0.35614 (9)	0.23084 (12)	0.79476 (14)	0.0510 (5)
N5	0.26758 (9)	0.19548 (12)	0.81838 (13)	0.0494 (5)
O1	0.15912 (8)	0.40913 (13)	0.53964 (13)	0.0688 (5)
O2	0.26452 (7)	0.25565 (10)	0.68598 (11)	0.0513 (4)
O3	0.26588 (9)	0.12670 (15)	0.94629 (15)	0.0855 (7)
H20	0.3454	0.4038	0.7553	0.128*
C35	0.5532 (2)	0.4402 (4)	0.8065 (4)	0.0697 (15)	0.50
H35A	0.5858	0.4492	0.7857	0.105*	0.50
H35B	0.5644	0.4548	0.8711	0.105*	0.50
H35C	0.5205	0.4729	0.7703	0.105*	0.50
O5	0.53385 (15)	0.3409 (4)	0.7931 (3)	0.0959 (18)	0.50
H35	0.5000	0.3679	0.7500	0.144*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0490 (14)	0.0654 (16)	0.0556 (15)	0.0017 (12)	0.0153 (12)	0.0043 (12)
C2	0.0726 (19)	0.090 (2)	0.0585 (17)	0.0144 (16)	0.0187 (15)	0.0178 (15)
C3	0.071 (2)	0.119 (3)	0.0589 (18)	0.0104 (19)	0.0004 (16)	0.0188 (18)
C4	0.0460 (16)	0.128 (3)	0.081 (2)	−0.0047 (18)	−0.0044 (15)	0.015 (2)
C5	0.0473 (15)	0.094 (2)	0.0680 (17)	0.0001 (14)	0.0156 (13)	0.0115 (16)
C6	0.0442 (12)	0.0444 (12)	0.0483 (13)	0.0035 (10)	0.0080 (10)	−0.0035 (10)
C7	0.0442 (12)	0.0446 (12)	0.0427 (12)	−0.0025 (10)	0.0129 (10)	−0.0002 (9)
C8	0.0472 (13)	0.0523 (13)	0.0431 (13)	0.0004 (10)	0.0100 (10)	0.0033 (10)
C9	0.0455 (12)	0.0461 (12)	0.0508 (13)	−0.0005 (10)	0.0158 (10)	0.0040 (10)
C10	0.0455 (13)	0.0617 (15)	0.0686 (17)	−0.0002 (11)	0.0146 (12)	0.0048 (13)
C11	0.0464 (14)	0.0698 (18)	0.093 (2)	0.0073 (13)	0.0277 (15)	0.0050 (16)
C12	0.0618 (17)	0.0650 (17)	0.091 (2)	0.0062 (14)	0.0415 (17)	−0.0021 (15)
C13	0.0620 (16)	0.0545 (14)	0.0664 (16)	0.0029 (12)	0.0310 (13)	−0.0028 (12)
C14	0.0474 (12)	0.0390 (11)	0.0528 (13)	0.0007 (9)	0.0198 (11)	0.0029 (10)
C15	0.0465 (12)	0.0510 (13)	0.0396 (12)	0.0012 (10)	0.0145 (10)	−0.0007 (10)
C16	0.0686 (16)	0.0552 (14)	0.0501 (14)	0.0009 (12)	0.0263 (12)	0.0080 (11)
C17	0.0759 (18)	0.0719 (18)	0.0549 (15)	0.0002 (14)	0.0354 (14)	0.0089 (13)
C18	0.0617 (16)	0.0774 (18)	0.0519 (14)	0.0054 (13)	0.0284 (12)	−0.0057 (13)
C19	0.0525 (14)	0.0556 (14)	0.0519 (13)	0.0061 (11)	0.0174 (11)	−0.0013 (11)
C20	0.0439 (12)	0.0536 (13)	0.0389 (11)	−0.0010 (10)	0.0133 (10)	0.0047 (10)
C21	0.0489 (13)	0.0415 (11)	0.0468 (13)	0.0020 (10)	0.0170 (10)	0.0027 (10)
C22	0.0532 (14)	0.0446 (12)	0.0536 (14)	0.0046 (11)	0.0104 (11)	0.0031 (11)
C23	0.0557 (16)	0.0647 (16)	0.0731 (18)	−0.0019 (13)	0.0101 (14)	0.0070 (14)
C24	0.0592 (17)	0.077 (2)	0.078 (2)	0.0017 (15)	−0.0017 (15)	0.0021 (16)
C25	0.077 (2)	0.078 (2)	0.0643 (18)	0.0122 (16)	−0.0001 (16)	0.0130 (16)
C26	0.078 (2)	0.0664 (17)	0.0570 (16)	0.0106 (15)	0.0134 (14)	0.0137 (14)
C27	0.0611 (15)	0.0498 (13)	0.0492 (14)	0.0069 (11)	0.0143 (12)	0.0060 (11)
C28	0.0609 (15)	0.0572 (15)	0.0525 (14)	0.0055 (12)	0.0191 (12)	0.0130 (12)
C29	0.0480 (13)	0.0471 (12)	0.0458 (12)	−0.0003 (10)	0.0181 (10)	0.0076 (10)
C30	0.0643 (16)	0.0556 (14)	0.0570 (15)	0.0019 (12)	0.0182 (13)	−0.0006 (12)
C31	0.0647 (18)	0.079 (2)	0.0650 (18)	−0.0138 (15)	0.0076 (14)	−0.0048 (15)
C32	0.0490 (15)	0.088 (2)	0.0686 (18)	0.0013 (14)	0.0126 (13)	0.0145 (16)
C33	0.0608 (17)	0.0680 (17)	0.088 (2)	0.0112 (14)	0.0292 (16)	0.0046 (16)
C34	0.0552 (15)	0.0544 (15)	0.0740 (17)	−0.0031 (12)	0.0214 (13)	−0.0056 (13)
N1	0.0453 (11)	0.0629 (12)	0.0463 (11)	0.0034 (9)	0.0140 (9)	−0.0051 (9)
N2	0.0471 (11)	0.0502 (11)	0.0477 (11)	0.0012 (8)	0.0155 (9)	−0.0053 (9)
N3	0.0470 (11)	0.0496 (11)	0.0419 (10)	0.0021 (8)	0.0158 (8)	−0.0001 (8)
N4	0.0492 (11)	0.0518 (11)	0.0505 (11)	0.0022 (9)	0.0153 (9)	0.0058 (9)
N5	0.0513 (11)	0.0480 (10)	0.0500 (11)	0.0031 (9)	0.0190 (9)	0.0110 (9)
O1	0.0585 (11)	0.0912 (14)	0.0487 (11)	0.0062 (10)	0.0088 (9)	−0.0088 (10)
O2	0.0474 (9)	0.0591 (10)	0.0468 (9)	0.0021 (7)	0.0156 (7)	0.0142 (7)
O3	0.0739 (14)	0.1109 (17)	0.0767 (14)	0.0072 (12)	0.0324 (11)	0.0445 (13)
C35	0.053 (3)	0.090 (4)	0.062 (3)	−0.010 (3)	0.014 (3)	−0.016 (3)
O5	0.0276 (17)	0.201 (6)	0.058 (2)	−0.005 (2)	0.0139 (16)	0.020 (3)

Geometric parameters (Å, º) top

C1—C6	1.371 (4)	C19—H19	0.9300
C1—C2	1.373 (4)	C20—O2	1.401 (3)
C1—H1	0.9300	C21—N4	1.270 (3)
C2—C3	1.372 (4)	C21—O2	1.349 (3)
C2—H2	0.9300	C21—N5	1.380 (3)
C3—C4	1.357 (5)	C22—C27	1.386 (4)
C3—H3	0.9300	C22—C23	1.389 (4)
C4—C5	1.393 (4)	C22—N4	1.400 (3)
C4—H4	0.9300	C23—C24	1.382 (4)
C5—C6	1.379 (3)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.378 (5)
C6—N1	1.419 (3)	C24—H24	0.9300
C7—N2	1.292 (3)	C25—C26	1.369 (4)
C7—N1	1.361 (3)	C25—H25	0.9300
C7—N3	1.398 (3)	C26—C27	1.392 (4)
C8—O1	1.214 (3)	C26—H26	0.9300
C8—N3	1.402 (3)	C27—C28	1.456 (4)
C8—C9	1.458 (3)	C28—O3	1.224 (3)
C9—C10	1.392 (3)	C28—N5	1.404 (3)
C9—C14	1.400 (3)	C29—C30	1.371 (4)
C10—C11	1.373 (4)	C29—C34	1.374 (3)
C10—H10	0.9300	C29—N5	1.448 (3)
C11—C12	1.378 (4)	C30—C31	1.380 (4)
C11—H11	0.9300	C30—H30	0.9300
C12—C13	1.373 (4)	C31—C32	1.375 (4)
C12—H12	0.9300	C31—H31	0.9300
C13—C14	1.394 (3)	C32—C33	1.375 (4)
C13—H13	0.9300	C32—H32	0.9300
C14—N2	1.379 (3)	C33—C34	1.379 (4)
C15—C16	1.376 (3)	C33—H33	0.9300
C15—C20	1.383 (3)	C34—H34	0.9300
C15—N3	1.445 (3)	N1—H20	0.9098
C16—C17	1.383 (4)	C35—O5	1.698 (9)
C16—H16	0.9300	C35—H35A	0.9600
C17—C18	1.376 (4)	C35—H35B	0.9600
C17—H17	0.9300	C35—H35C	0.9600
C18—C19	1.386 (4)	O5—O5ⁱ	1.711 (7)
C18—H18	0.9300	O5—H35	0.9646
C19—C20	1.372 (3)

C6—C1—C2	120.1 (3)	N4—C21—N5	127.1 (2)
C6—C1—H1	119.9	O2—C21—N5	109.81 (19)
C2—C1—H1	119.9	C27—C22—C23	119.2 (2)
C3—C2—C1	120.6 (3)	C27—C22—N4	122.3 (2)
C3—C2—H2	119.7	C23—C22—N4	118.5 (2)
C1—C2—H2	119.7	C24—C23—C22	119.9 (3)
C4—C3—C2	119.5 (3)	C24—C23—H23	120.1
C4—C3—H3	120.2	C22—C23—H23	120.1
C2—C3—H3	120.2	C25—C24—C23	120.6 (3)
C3—C4—C5	120.7 (3)	C25—C24—H24	119.7
C3—C4—H4	119.6	C23—C24—H24	119.7
C5—C4—H4	119.6	C26—C25—C24	119.9 (3)
C6—C5—C4	119.3 (3)	C26—C25—H25	120.1
C6—C5—H5	120.3	C24—C25—H25	120.1
C4—C5—H5	120.3	C25—C26—C27	120.1 (3)
C1—C6—C5	119.7 (2)	C25—C26—H26	119.9
C1—C6—N1	123.4 (2)	C27—C26—H26	119.9
C5—C6—N1	116.7 (2)	C22—C27—C26	120.2 (3)
N2—C7—N1	120.6 (2)	C22—C27—C28	119.9 (2)
N2—C7—N3	124.1 (2)	C26—C27—C28	119.9 (3)
N1—C7—N3	115.27 (19)	O3—C28—N5	119.7 (2)
O1—C8—N3	120.3 (2)	O3—C28—C27	126.1 (2)
O1—C8—C9	125.4 (2)	N5—C28—C27	114.2 (2)
N3—C8—C9	114.3 (2)	C30—C29—C34	120.8 (2)
C10—C9—C14	120.1 (2)	C30—C29—N5	119.8 (2)
C10—C9—C8	120.6 (2)	C34—C29—N5	119.4 (2)
C14—C9—C8	119.3 (2)	C29—C30—C31	119.5 (3)
C11—C10—C9	120.1 (3)	C29—C30—H30	120.2
C11—C10—H10	120.0	C31—C30—H30	120.2
C9—C10—H10	120.0	C32—C31—C30	120.2 (3)
C10—C11—C12	119.8 (2)	C32—C31—H31	119.9
C10—C11—H11	120.1	C30—C31—H31	119.9
C12—C11—H11	120.1	C31—C32—C33	119.7 (3)
C13—C12—C11	121.2 (3)	C31—C32—H32	120.2
C13—C12—H12	119.4	C33—C32—H32	120.2
C11—C12—H12	119.4	C32—C33—C34	120.5 (3)
C12—C13—C14	120.0 (3)	C32—C33—H33	119.7
C12—C13—H13	120.0	C34—C33—H33	119.7
C14—C13—H13	120.0	C29—C34—C33	119.2 (3)
N2—C14—C13	118.3 (2)	C29—C34—H34	120.4
N2—C14—C9	122.8 (2)	C33—C34—H34	120.4
C13—C14—C9	118.9 (2)	C7—N1—C6	125.7 (2)
C16—C15—C20	120.1 (2)	C7—N1—H20	115.7
C16—C15—N3	120.2 (2)	C6—N1—H20	117.9
C20—C15—N3	119.72 (19)	C7—N2—C14	117.8 (2)
C15—C16—C17	119.2 (2)	C7—N3—C8	121.65 (19)
C15—C16—H16	120.4	C7—N3—C15	120.48 (19)
C17—C16—H16	120.4	C8—N3—C15	117.77 (18)
C18—C17—C16	120.3 (2)	C21—N4—C22	116.2 (2)
C18—C17—H17	119.8	C21—N5—C28	120.2 (2)
C16—C17—H17	119.8	C21—N5—C29	120.49 (18)
C17—C18—C19	120.7 (2)	C28—N5—C29	119.28 (19)
C17—C18—H18	119.7	C21—O2—C20	119.30 (17)
C19—C18—H18	119.7	O5—C35—H35A	109.5
C20—C19—C18	118.6 (2)	O5—C35—H35B	109.5
C20—C19—H19	120.7	H35A—C35—H35B	109.5
C18—C19—H19	120.7	O5—C35—H35C	109.5
C19—C20—C15	121.1 (2)	H35A—C35—H35C	109.5
C19—C20—O2	121.9 (2)	H35B—C35—H35C	109.5
C15—C20—O2	116.73 (19)	C35—O5—O5ⁱ	104.1 (2)
N4—C21—O2	123.1 (2)

C6—C1—C2—C3	−0.7 (5)	C34—C29—C30—C31	0.9 (4)
C1—C2—C3—C4	0.3 (6)	N5—C29—C30—C31	−177.9 (2)
C2—C3—C4—C5	0.1 (6)	C29—C30—C31—C32	−0.2 (4)
C3—C4—C5—C6	−0.1 (6)	C30—C31—C32—C33	−0.2 (5)
C2—C1—C6—C5	0.7 (4)	C31—C32—C33—C34	0.0 (5)
C2—C1—C6—N1	175.8 (3)	C30—C29—C34—C33	−1.1 (4)
C4—C5—C6—C1	−0.3 (4)	N5—C29—C34—C33	177.7 (2)
C4—C5—C6—N1	−175.8 (3)	C32—C33—C34—C29	0.6 (4)
O1—C8—C9—C10	−0.7 (4)	N2—C7—N1—C6	19.3 (4)
N3—C8—C9—C10	179.9 (2)	N3—C7—N1—C6	−161.8 (2)
O1—C8—C9—C14	178.1 (2)	C1—C6—N1—C7	27.8 (4)
N3—C8—C9—C14	−1.2 (3)	C5—C6—N1—C7	−156.9 (2)
C14—C9—C10—C11	0.4 (4)	N1—C7—N2—C14	−179.0 (2)
C8—C9—C10—C11	179.3 (2)	N3—C7—N2—C14	2.3 (3)
C9—C10—C11—C12	0.0 (4)	C13—C14—N2—C7	179.1 (2)
C10—C11—C12—C13	0.0 (5)	C9—C14—N2—C7	−0.6 (3)
C11—C12—C13—C14	−0.3 (4)	N2—C7—N3—C8	−3.6 (3)
C12—C13—C14—N2	−179.0 (2)	N1—C7—N3—C8	177.6 (2)
C12—C13—C14—C9	0.7 (4)	N2—C7—N3—C15	−179.8 (2)
C10—C9—C14—N2	179.0 (2)	N1—C7—N3—C15	1.3 (3)
C8—C9—C14—N2	0.1 (3)	O1—C8—N3—C7	−176.6 (2)
C10—C9—C14—C13	−0.7 (3)	C9—C8—N3—C7	2.8 (3)
C8—C9—C14—C13	−179.6 (2)	O1—C8—N3—C15	−0.2 (3)
C20—C15—C16—C17	−0.5 (4)	C9—C8—N3—C15	179.16 (19)
N3—C15—C16—C17	−180.0 (2)	C16—C15—N3—C7	−103.9 (3)
C15—C16—C17—C18	1.2 (4)	C20—C15—N3—C7	76.6 (3)
C16—C17—C18—C19	−1.3 (4)	C16—C15—N3—C8	79.7 (3)
C17—C18—C19—C20	0.7 (4)	C20—C15—N3—C8	−99.8 (3)
C18—C19—C20—C15	0.0 (4)	O2—C21—N4—C22	179.8 (2)
C18—C19—C20—O2	173.7 (2)	N5—C21—N4—C22	0.0 (4)
C16—C15—C20—C19	−0.1 (4)	C27—C22—N4—C21	3.1 (3)
N3—C15—C20—C19	179.4 (2)	C23—C22—N4—C21	−178.1 (2)
C16—C15—C20—O2	−174.2 (2)	N4—C21—N5—C28	−3.7 (4)
N3—C15—C20—O2	5.3 (3)	O2—C21—N5—C28	176.5 (2)
C27—C22—C23—C24	−0.5 (4)	N4—C21—N5—C29	175.2 (2)
N4—C22—C23—C24	−179.3 (3)	O2—C21—N5—C29	−4.6 (3)
C22—C23—C24—C25	1.0 (5)	O3—C28—N5—C21	−176.4 (2)
C23—C24—C25—C26	−0.5 (5)	C27—C28—N5—C21	3.9 (3)
C24—C25—C26—C27	−0.6 (5)	O3—C28—N5—C29	4.7 (4)
C23—C22—C27—C26	−0.6 (4)	C27—C28—N5—C29	−175.0 (2)
N4—C22—C27—C26	178.2 (2)	C30—C29—N5—C21	92.6 (3)
C23—C22—C27—C28	178.7 (2)	C34—C29—N5—C21	−86.1 (3)
N4—C22—C27—C28	−2.5 (4)	C30—C29—N5—C28	−88.5 (3)
C25—C26—C27—C22	1.2 (4)	C34—C29—N5—C28	92.8 (3)
C25—C26—C27—C28	−178.1 (3)	N4—C21—O2—C20	−6.0 (3)
C22—C27—C28—O3	179.3 (3)	N5—C21—O2—C20	173.79 (18)
C26—C27—C28—O3	−1.3 (4)	C19—C20—O2—C21	73.6 (3)
C22—C27—C28—N5	−1.0 (3)	C15—C20—O2—C21	−112.4 (2)
C26—C27—C28—N5	178.3 (2)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C29–C34 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H35···O5ⁱ	0.96	0.96	1.711 (7)	125
C2—H2···Cg1ⁱⁱ	0.93	2.75	3.617 (3)	155

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1/2, −y+1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₃₄H₂₃N₅O₃·0.5CH₄O
M_r	565.60
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	292
a, b, c (Å)	24.268 (2), 16.5049 (14), 15.2929 (12)
β (°)	110.382 (1)
V (Å³)	5741.9 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.25 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.963, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	16455, 5631, 3943
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.228, 1.04
No. of reflections	5631
No. of parameters	397
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.26

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C29–C34 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H35···O5ⁱ	0.96	0.96	1.711 (7)	124.9
C2—H2···Cg1ⁱⁱ	0.93	2.75	3.617 (3)	155

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1/2, −y+1/2, −z+2.

Acknowledgements

The authors are grateful to the Natural Science Foundation of Guizhou Educational Committee (grant No. 20090079) for financial support, and acknowledge the Sophisticated Analytical Instrument Facility, Central China Normal University, Wuhan, for the data collection.

References

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Volume 66| Part 8| August 2010| Pages o2075-o2076

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

2-[2-(2-Anilino-4-oxo-3,4-di­hydro­quinazolin-3-yl)phen­­oxy]-3-phenyl­quinazolin-4(3H)-one methanol hemisolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[2-(2-Anilino-4-oxo-3,4-dihydroquinazolin-3-yl)phenoxy]-3-phenylquinazolin-4(3H)-one methanol hemisolvate