2-(4-Hydr­oxy-3-methoxy­phen­yl)-1-phenethyl-1,2-dihydro­quinazolin-4(3H)-one

In the crystal structure of the title compound, C₂₃H₂₂N₂O₃, the dihydro­pyrimidine (DHPM) ring adopts a sofa conformation. The methoxy-substituted benzene ring is oriented equatorially and the phenylethyl group has a fully extended conformation with respect to the DHPM ring. Four adjacent mol­ecules are linked via N—H...O and O—H...O hydrogen-bonding inter­actions, generating a tetra­meric unit. The crystal structure is further stabilized by C—H...π(arene) inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.058
• wR factor = 0.193
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11    ..  O2      ..       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7     ..  CG1     ..       3.01 Ang.

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           28.01
           From the CIF: _reflns_number_total               4349
           From the CIF: _diffrn_reflns_limit_ max hkl   45.    8.   21.
           From the CIF: _diffrn_reflns_limit_ min hkl  -39.   -8.  -20.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   47.    9.   21.
           Calculated minimum hkl  -47.   -9.  -21.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

2-(4-Hydroxy-3-methoxyphenyl)-1-phenethyl-1,2-dihydroquinazolin-4(3H)-one

Crystal data

C23H22N2O3	F(000) = 1584
Mr = 374.43	Dx = 1.321 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 36.113 (5) Å	Cell parameters from 1838 reflections
b = 6.8124 (9) Å	θ = 2.3–22.7°
c = 15.931 (2) Å	µ = 0.09 mm^−1
β = 105.504 (2)°	T = 273 K
V = 3776.7 (9) Å^3	Block, colourless
Z = 8	0.22 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2519 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 28.0°, θmin = 1.2°
ω scans	h = −39→45
11047 measured reflections	k = −8→8
4349 independent reflections	l = −20→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.193	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.1049P)^2 + 0.0523P] where P = (Fo^2 + 2Fc^2)/3
4349 reflections	(Δ/σ)max < 0.001
256 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C2	0.15998 (7)	0.5635 (3)	0.07359 (14)	0.0407 (6)
H2	0.1611	0.6567	0.0275	0.049*
C3	0.09906 (7)	0.4264 (4)	−0.00534 (15)	0.0454 (6)
C4	0.11904 (7)	0.2977 (4)	−0.04638 (14)	0.0463 (6)
C5	0.15997 (7)	0.2580 (3)	−0.00717 (14)	0.0432 (6)
C6	0.09939 (9)	0.1951 (4)	−0.12039 (17)	0.0636 (8)
H6	0.1129	0.1108	−0.1474	0.076*
C7	0.06046 (10)	0.2160 (5)	−0.1543 (2)	0.0775 (10)
H7	0.0476	0.1484	−0.2043	0.093*
C8	0.04092 (9)	0.3380 (5)	−0.1132 (2)	0.0729 (9)
H8	0.0144	0.3503	−0.1352	0.087*
C9	0.05936 (8)	0.4439 (4)	−0.03958 (18)	0.0596 (7)
H9	0.0453	0.5264	−0.0131	0.072*
C10	0.18199 (7)	0.6472 (3)	0.15968 (14)	0.0383 (5)
C11	0.19837 (7)	0.8302 (3)	0.16495 (14)	0.0414 (6)
H11	0.1971	0.9010	0.1143	0.050*
C12	0.21685 (7)	0.9103 (3)	0.24529 (15)	0.0424 (6)
H12	0.2278	1.0345	0.2482	0.051*
C13	0.21904 (6)	0.8071 (3)	0.32046 (14)	0.0378 (5)
C14	0.20387 (7)	0.6172 (3)	0.31582 (13)	0.0387 (5)
C15	0.18545 (7)	0.5389 (3)	0.23617 (14)	0.0412 (6)
H15	0.1752	0.4130	0.2330	0.049*
C16	0.10010 (7)	0.6707 (4)	0.10967 (15)	0.0467 (6)
H16A	0.1149	0.6884	0.1697	0.056*
H16B	0.0752	0.6187	0.1105	0.056*
C17	0.09414 (8)	0.8708 (4)	0.06556 (17)	0.0548 (7)
H17A	0.1186	0.9201	0.0600	0.066*
H17B	0.0770	0.8577	0.0075	0.066*
C18	0.07749 (8)	1.0136 (4)	0.11685 (16)	0.0482 (6)
C19	0.03835 (8)	1.0278 (4)	0.10434 (19)	0.0624 (8)
H19	0.0221	0.9486	0.0628	0.075*
C20	0.02265 (9)	1.1571 (5)	0.1522 (2)	0.0738 (9)
H20	−0.0039	1.1647	0.1427	0.089*
C21	0.04621 (11)	1.2731 (5)	0.2133 (2)	0.0709 (9)
H21	0.0358	1.3626	0.2448	0.085*
C22	0.08532 (10)	1.2580 (4)	0.2285 (2)	0.0702 (9)
H22	0.1015	1.3353	0.2710	0.084*
C23	0.10052 (8)	1.1289 (4)	0.1810 (2)	0.0613 (7)
H23	0.1271	1.1187	0.1922	0.074*
C24	0.20276 (10)	0.3226 (4)	0.39426 (17)	0.0676 (9)
H24A	0.1756	0.2987	0.3746	0.101*
H24B	0.2125	0.2723	0.4523	0.101*
H24C	0.2154	0.2582	0.3560	0.101*
N1	0.17740 (6)	0.3795 (3)	0.05767 (12)	0.0461 (5)
H1'	0.1995	0.3477	0.0908	0.099 (12)*
N2	0.11956 (6)	0.5252 (3)	0.06940 (12)	0.0428 (5)
O2	0.17711 (5)	0.1178 (3)	−0.02895 (11)	0.0546 (5)
O1	0.23787 (5)	0.8869 (3)	0.39914 (10)	0.0493 (5)
H1	0.2250	0.8705	0.4340	0.074*
O3	0.20966 (6)	0.5247 (2)	0.39410 (10)	0.0546 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0465 (14)	0.0433 (13)	0.0342 (11)	0.0000 (11)	0.0142 (10)	0.0006 (10)
C3	0.0487 (15)	0.0443 (14)	0.0413 (12)	−0.0047 (11)	0.0088 (11)	0.0062 (10)
C4	0.0599 (16)	0.0406 (14)	0.0371 (12)	−0.0064 (12)	0.0106 (11)	0.0016 (10)
C5	0.0595 (16)	0.0402 (14)	0.0333 (11)	−0.0025 (12)	0.0185 (11)	0.0007 (10)
C6	0.081 (2)	0.0524 (17)	0.0501 (15)	−0.0059 (15)	0.0051 (14)	−0.0071 (13)
C7	0.087 (3)	0.062 (2)	0.0640 (19)	−0.0143 (18)	−0.0145 (18)	−0.0062 (16)
C8	0.061 (2)	0.069 (2)	0.074 (2)	−0.0154 (16)	−0.0074 (16)	0.0045 (17)
C9	0.0527 (18)	0.0582 (17)	0.0637 (17)	−0.0056 (13)	0.0081 (14)	0.0050 (13)
C10	0.0406 (13)	0.0394 (13)	0.0369 (11)	−0.0002 (10)	0.0138 (10)	−0.0020 (9)
C11	0.0481 (14)	0.0404 (13)	0.0390 (12)	0.0007 (11)	0.0172 (10)	0.0034 (10)
C12	0.0436 (14)	0.0380 (13)	0.0497 (13)	−0.0078 (10)	0.0198 (11)	−0.0017 (10)
C13	0.0337 (12)	0.0411 (13)	0.0398 (12)	−0.0015 (10)	0.0119 (9)	−0.0065 (10)
C14	0.0491 (14)	0.0362 (13)	0.0340 (11)	0.0054 (10)	0.0165 (10)	−0.0009 (9)
C15	0.0485 (15)	0.0344 (13)	0.0439 (13)	−0.0028 (10)	0.0180 (11)	−0.0023 (10)
C16	0.0478 (15)	0.0489 (15)	0.0463 (13)	0.0031 (11)	0.0174 (11)	0.0025 (11)
C17	0.0624 (18)	0.0518 (16)	0.0538 (15)	0.0059 (13)	0.0217 (13)	0.0096 (12)
C18	0.0525 (16)	0.0428 (14)	0.0509 (14)	0.0065 (12)	0.0163 (12)	0.0130 (11)
C19	0.0520 (18)	0.068 (2)	0.0618 (17)	0.0101 (14)	0.0060 (14)	0.0012 (14)
C20	0.0539 (19)	0.084 (2)	0.086 (2)	0.0163 (17)	0.0227 (17)	0.0088 (18)
C21	0.090 (3)	0.0545 (19)	0.081 (2)	0.0086 (17)	0.0448 (19)	0.0041 (16)
C22	0.080 (2)	0.0552 (18)	0.079 (2)	−0.0132 (16)	0.0285 (18)	−0.0093 (16)
C23	0.0518 (17)	0.0510 (17)	0.0812 (19)	−0.0056 (13)	0.0178 (15)	0.0020 (15)
C24	0.120 (3)	0.0410 (16)	0.0487 (15)	0.0093 (16)	0.0346 (16)	0.0084 (12)
N1	0.0490 (13)	0.0521 (13)	0.0365 (10)	0.0064 (10)	0.0104 (9)	−0.0055 (9)
N2	0.0447 (12)	0.0449 (12)	0.0413 (10)	−0.0011 (9)	0.0159 (9)	−0.0026 (8)
O2	0.0725 (13)	0.0432 (10)	0.0535 (10)	0.0023 (9)	0.0263 (9)	−0.0047 (8)
O1	0.0519 (11)	0.0531 (11)	0.0430 (9)	−0.0096 (8)	0.0130 (8)	−0.0107 (8)
O3	0.0879 (14)	0.0404 (10)	0.0355 (8)	0.0014 (9)	0.0164 (9)	0.0010 (7)

Geometric parameters (Å, º)

C2—N1	1.455 (3)	C14—C15	1.374 (3)
C2—N2	1.467 (3)	C15—H15	0.9300
C2—C10	1.502 (3)	C16—N2	1.459 (3)
C2—H2	0.9800	C16—C17	1.523 (3)
C3—N2	1.395 (3)	C16—H16A	0.9700
C3—C9	1.396 (4)	C16—H16B	0.9700
C3—C4	1.404 (4)	C17—C18	1.496 (4)
C4—C6	1.391 (3)	C17—H17A	0.9700
C4—C5	1.468 (4)	C17—H17B	0.9700
C5—O2	1.237 (3)	C18—C19	1.377 (4)
C5—N1	1.342 (3)	C18—C23	1.377 (4)
C6—C7	1.372 (4)	C19—C20	1.382 (4)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.366 (5)	C20—C21	1.362 (4)
C7—H7	0.9300	C20—H20	0.9300
C8—C9	1.386 (4)	C21—C22	1.372 (4)
C8—H8	0.9300	C21—H21	0.9300
C9—H9	0.9300	C22—C23	1.368 (4)
C10—C11	1.373 (3)	C22—H22	0.9300
C10—C15	1.401 (3)	C23—H23	0.9300
C11—C12	1.387 (3)	C24—O3	1.399 (3)
C11—H11	0.9300	C24—H24A	0.9600
C12—C13	1.373 (3)	C24—H24B	0.9600
C12—H12	0.9300	C24—H24C	0.9600
C13—O1	1.369 (2)	N1—H1'	0.8600
C13—C14	1.399 (3)	O1—H1	0.8200
C14—O3	1.363 (3)
N1—C2—N2	108.08 (19)	N2—C16—C17	115.5 (2)
N1—C2—C10	109.77 (19)	N2—C16—H16A	108.4
N2—C2—C10	112.74 (18)	C17—C16—H16A	108.4
N1—C2—H2	108.7	N2—C16—H16B	108.4
N2—C2—H2	108.7	C17—C16—H16B	108.4
C10—C2—H2	108.7	H16A—C16—H16B	107.5
N2—C3—C9	123.2 (2)	C18—C17—C16	111.0 (2)
N2—C3—C4	118.5 (2)	C18—C17—H17A	109.4
C9—C3—C4	118.3 (2)	C16—C17—H17A	109.4
C6—C4—C3	120.0 (3)	C18—C17—H17B	109.4
C6—C4—C5	119.7 (3)	C16—C17—H17B	109.4
C3—C4—C5	120.1 (2)	H17A—C17—H17B	108.0
O2—C5—N1	121.7 (2)	C19—C18—C23	117.4 (3)
O2—C5—C4	123.0 (2)	C19—C18—C17	120.9 (3)
N1—C5—C4	115.2 (2)	C23—C18—C17	121.6 (3)
C7—C6—C4	121.3 (3)	C18—C19—C20	121.4 (3)
C7—C6—H6	119.4	C18—C19—H19	119.3
C4—C6—H6	119.4	C20—C19—H19	119.3
C8—C7—C6	118.7 (3)	C21—C20—C19	119.6 (3)
C8—C7—H7	120.6	C21—C20—H20	120.2
C6—C7—H7	120.6	C19—C20—H20	120.2
C7—C8—C9	122.0 (3)	C20—C21—C22	119.9 (3)
C7—C8—H8	119.0	C20—C21—H21	120.0
C9—C8—H8	119.0	C22—C21—H21	120.0
C8—C9—C3	119.8 (3)	C23—C22—C21	119.8 (3)
C8—C9—H9	120.1	C23—C22—H22	120.1
C3—C9—H9	120.1	C21—C22—H22	120.1
C11—C10—C15	119.2 (2)	C22—C23—C18	121.7 (3)
C11—C10—C2	121.0 (2)	C22—C23—H23	119.2
C15—C10—C2	119.8 (2)	C18—C23—H23	119.2
C10—C11—C12	120.5 (2)	O3—C24—H24A	109.5
C10—C11—H11	119.8	O3—C24—H24B	109.5
C12—C11—H11	119.8	H24A—C24—H24B	109.5
C13—C12—C11	120.3 (2)	O3—C24—H24C	109.5
C13—C12—H12	119.8	H24A—C24—H24C	109.5
C11—C12—H12	119.8	H24B—C24—H24C	109.5
O1—C13—C12	119.6 (2)	C5—N1—C2	122.0 (2)
O1—C13—C14	120.5 (2)	C5—N1—H1'	119.0
C12—C13—C14	119.8 (2)	C2—N1—H1'	119.0
O3—C14—C15	125.7 (2)	C3—N2—C16	119.6 (2)
O3—C14—C13	114.67 (19)	C3—N2—C2	114.78 (19)
C15—C14—C13	119.6 (2)	C16—N2—C2	116.72 (18)
C14—C15—C10	120.5 (2)	C13—O1—H1	109.5
C14—C15—H15	119.8	C14—O3—C24	118.24 (18)
C10—C15—H15	119.8
N2—C3—C4—C6	179.2 (2)	C11—C10—C15—C14	2.2 (3)
C9—C3—C4—C6	1.5 (4)	C2—C10—C15—C14	−176.8 (2)
N2—C3—C4—C5	4.5 (3)	N2—C16—C17—C18	−174.5 (2)
C9—C3—C4—C5	−173.2 (2)	C16—C17—C18—C19	−87.0 (3)
C6—C4—C5—O2	−10.5 (4)	C16—C17—C18—C23	89.8 (3)
C3—C4—C5—O2	164.2 (2)	C23—C18—C19—C20	2.1 (4)
C6—C4—C5—N1	172.6 (2)	C17—C18—C19—C20	179.0 (3)
C3—C4—C5—N1	−12.7 (3)	C18—C19—C20—C21	−0.2 (5)
C3—C4—C6—C7	−0.4 (4)	C19—C20—C21—C22	−1.5 (5)
C5—C4—C6—C7	174.3 (3)	C20—C21—C22—C23	1.2 (5)
C4—C6—C7—C8	−1.0 (5)	C21—C22—C23—C18	0.7 (4)
C6—C7—C8—C9	1.4 (5)	C19—C18—C23—C22	−2.3 (4)
C7—C8—C9—C3	−0.4 (5)	C17—C18—C23—C22	−179.3 (2)
N2—C3—C9—C8	−178.7 (2)	O2—C5—N1—C2	168.8 (2)
C4—C3—C9—C8	−1.1 (4)	C4—C5—N1—C2	−14.4 (3)
N1—C2—C10—C11	121.3 (2)	N2—C2—N1—C5	45.5 (3)
N2—C2—C10—C11	−118.1 (2)	C10—C2—N1—C5	168.8 (2)
N1—C2—C10—C15	−59.7 (3)	C9—C3—N2—C16	−6.9 (3)
N2—C2—C10—C15	60.9 (3)	C4—C3—N2—C16	175.5 (2)
C15—C10—C11—C12	−2.5 (3)	C9—C3—N2—C2	−153.3 (2)
C2—C10—C11—C12	176.5 (2)	C4—C3—N2—C2	29.1 (3)
C10—C11—C12—C13	0.2 (4)	C17—C16—N2—C3	−78.8 (3)
C11—C12—C13—O1	179.0 (2)	C17—C16—N2—C2	66.9 (3)
C11—C12—C13—C14	2.5 (3)	N1—C2—N2—C3	−51.4 (2)
O1—C13—C14—O3	−0.2 (3)	C10—C2—N2—C3	−172.90 (19)
C12—C13—C14—O3	176.3 (2)	N1—C2—N2—C16	161.23 (18)
O1—C13—C14—C15	−179.3 (2)	C10—C2—N2—C16	39.7 (3)
C12—C13—C14—C15	−2.7 (3)	C15—C14—O3—C24	12.2 (4)
O3—C14—C15—C10	−178.6 (2)	C13—C14—O3—C24	−166.8 (2)
C13—C14—C15—C10	0.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1′···O1^i	0.86	2.24	2.952 (3)	140
O1—H1···O2^ii	0.82	1.97	2.734 (2)	154
C11—H11···O2^iii	0.93	2.65	3.564 (3)	167
C7—H7···Cg1^iv	0.93	3.01	3.78	141
C12—H12···Cg2^v	0.93	2.85	3.62	142

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