Two quinazolinones: a ring conformational study

The mol­ecules of (±)-2-(4-methoxy­phen­yl)-1-phenethyl-2,3-dihydro­quinazolin-4(1H)-one, C₂₃H₂₂N₂O₂, (I), and (±)-2-(1,3-benzodioxol-5-yl)-1-phenethyl-2,3-dihydro­quinazolin-4(1H)-one, C₂₃H₂₀N₂O₃, (II), have T-shaped forms in the crystal structure. The tetrahydro­pyrimidine ring in both structures adopts a sofa conformation. Both mol­ecules are linked by N—H...O and C—H...O hydrogen bonds to form sheets built from alternating R₂²(8) and R₄⁴(26) [R₄⁴(24) in (II)] edge-fused rings. Additionally, the structures are stabilized by extensive C—H...π inter­actions.

S1. Comment

Quinazolinone is a naturally occurring alkaloid and is an impotrant pharmacophore which occurs frequently in medicinal chemistry (Fry et al., 1994; Liu et al., 2006); it is also considered to be a privileged structure in drug discovery (Horton et al., 2003). Structural analysis of these compounds provides an opportunity to study the biological activity and its implications for the structural requirements for binding to the receptors. Ring conformation will often play a crucial role in the structure–activity relationship of the molecule (Fossheim et al., 1982). Furthermore, the substituents on the ring make a substantial contribution to the ring conformation. In continuation of our earlier studies (Swamy & Ravikumar, 2005a,b, 2006) on the influence of substituents on the dihydropyrimidine ring (DHPM) conformation, we report here the crystal structures of the two compounds (I) and (II).

Compounds (I) and (II) posses a stereogenic centre with a relative configuration at C2(S/R). The two molecules are in a `T'-shaped form (Figs. 1 and 2), with the DHPM ring as the junction point. In the molecules of both (I) and (II), atoms C2–C5, N1 and N2 form the pyrimidine ring. The bond lengths and angles about the molecular framework common to structures (I) and (II) are similar. The bond lengths and angles within the central DHPM ring are affected by conjugation. The formal single bonds N1—C5 and N2—C3 in both compounds have partial double-bond character (Tables 1 and 3) and are all shorter than the typical Csp²—N bond distance (1.426 Å; Lorente et al., 1995). As expected, the DHPM ring adopts an envelope conformation, with a Csp³ atom (i.e. atom C2) deviating by -0.624 (3) Å [0.626 (3) Å for (II)] from the least-squres plane defined by the remaining endocyclic atoms. The Cremer & Pople (1975) puckering parameters for (I) are Q_T = 0.453 (3) Å, θ = 64.4 (4)° and ϕ = 69.4 (4)° [0.460 (6) Å, 64.6 (7)° and 71.2 (8)° for (II)]. The sum of the absolute values of the internal torsion angles (close to zero) of the heterocyclic ring is a measure of planarity. It has been reported by Triggle et al. (1980) that there is an apparent correlation between the pharmacological activity and the planarity of the heterocyclic ring, meaning that increased planarity of the ring correlates with higher activity of the compound. Furthermore, it has been observed by Swamy & Ravikumar (2005a,b), that the substituent at the C2-position in the DHPM ring plays a crucial role on the ring conformation. A correlation has been observed between the bulkiness of the substituent and the DHPM ring conformation (Table 5). In Fig. 3, the molecular weight of the substituent (at the C2-position) is plotted versus θ_average (the average of the C2—N2—C3—C4 and C2—N1—C5—C4 angles) for several quinazolinones obtained from the literature. One can see that there is a near linear correlation between θ_average and the molecular weight of the substituent at the C2-position. The C5—O2 bond distance of 1.234 (3) Å in compounds (I) and (II) is consistent with but slightly longer than the normal C═O distance (1.20 Å) due to the effect of substantial conjugation involving atom O2 (Tiekink, 1989). The sum of the bond angles around atoms N1 and N2 [352.3 (1) and 350.7 (2)° in (I), and 356.6 (11) and 351.5 (2)° in (II)] indicates a pyramidal configuration. In both compounds, the phenethyl group has a fully extended conformation with respect to the central pyrimidine ring (Tables 1 and 3). In (I), with respect to the C12—C13 bond, the cis orientation of the C24—O1 bond about the O1—C13 bond [C24—O1—C13—C12 = -1.6 (4)°] results in repulsion between the H atoms attached to atoms C12 and C24, thereby causing the widening of the C12—C13—O1 angle and the narrowing of C14—C13—O1 from 120° (Table 1). Similar observations have been reported in the literature (Mukherjee et al., 2000, 2001).

The methoxyphenyl group of (I) is positioned equatorially at atom C2 of the pyrimidine ring, as defined by the average of the torsion angles C10—C2—N2—C3 and C10—C2—N1—C5 [172.5 (2)°]. Similarly, in (II), the benzodioxol group is also oriented equatorially [the average torsion angle for (II) is 173.4 (3)°] at C2.

In both structures, atom N1 of the pyrimidine ring acts as a hydrogen-bond donor to the quinazolinone atom O2 (Tables 2 and 4), so forming symmetric dimers of R²₂(8) type (Bernstein et al., 1995) along the c axis [the a axis in (II); Figs. 4 and 5]. These dimers are further connected into a continuous ladder-like chain of C10 type along the c axis. The combination of these two then generates a supramolecular two-dimensional network that consists of R²₂(26)-type [R²₂(24) in (II)] rings. The aromatic ring of the quinazolinone unit in (I) is involved in a C—H···π interaction (Table 2) with atom C24 of the methoxy group. In (II), the supramolecular network is further strengthened by weak π–π [the ring-centroid separation is 3.873 (4) Å] and extensive C—H···π interactions (Table 4).

In summary, substitution at the C2-position in the DHPM ring plays an important role in determining the ring conformation; increasing the bulkiness of the substituent group at C2 leads to more distortion in the DHPM ring, which in turn affects the ring conformation. Interestingly, the DHPM ring adopts an envelope conformation if the substituent at C2 is more bulky. Otherwise, if the substituent is compact (e.g. O, S, etc.), the ring aquires a half-chair or boat conformation (Chandra Mohan et al., 2003).

Related literature

For related literature, see: Bernstein et al. (1995); Chandra Mohan, Ravikumar, Shetty & Velmurugan (2003); Cremer & Pople (1975); Fossheim et al. (1982); Fry et al. (1994); Horton et al. (2003); Liu et al. (2006); Lorente et al. (1995); Mukherjee et al. (2000, 2001); Sadanandam et al. (1987); Swamy & Ravikumar (2005a, 2005b, 2006); Tiekink (1989); Triggle et al. (1980).

S2. Experimental

Compounds (I) and (II) were prepared according to a literature procedure (Sadanandam et al., 1987) and were recrystalized from methanol.

S3. Refinement

H atoms attached to N atoms were located in a difference density map and refined isotropically. All other H atoms were placed in geometrycally idealized positions and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å, and with U_iso(H)=1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for all other H atoms.

Computing details

For both compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Figures

	Fig. 1. The asymmetric unit of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The asymmetric unit of (II), showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 3. The correlation of the DHPM ring distortion with the bulkiness of the substituent group at the C2-position in the ring. The slope, intercept and correlation coefficient obtained by linear regression are 0.198, -1.40 and 0.92, respectively.
	Fig. 4. Part of the crystal structure of (I), highlighting the formation of centrosymmetric dimers through R^22 (8) and R^44 (26) e dge-fused rings along the c axis. Dashed lines indicate hydrogen bonds. For the sake of clarity, H atoms not involved in the motifs have been omitted.
	Fig. 5. Part of the crystal structure of (II), highlighting the formation of centrosymmetric dimers through R^22 (8) and R^44 (24) e dge-fused rings along the c axis. Dashed lines indicate hydrogen bonds. For the sake of clarity, H atoms not involved in the motifs have been omitted.

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

Crystal data

C23H22N2O2	Z = 2
Mr = 358.43	F(000) = 380
Triclinic, P1	Dx = 1.261 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7224 (15) Å	Cell parameters from 2135 reflections
b = 10.326 (2) Å	θ = 3.0–26.3°
c = 14.694 (3) Å	µ = 0.08 mm^−1
α = 109.331 (4)°	T = 293 K
β = 100.233 (4)°	Needles, colourless
γ = 90.803 (4)°	0.22 × 0.17 × 0.15 mm
V = 944.3 (3) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2172 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 25.0°, θmin = 1.5°
ω scans	h = −7→7
6526 measured reflections	k = −12→12
3281 independent reflections	l = −17→15

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.1048P)^2 + 0.0862P] where P = (Fo^2 + 2Fc^2)/3
3281 reflections	(Δ/σ)max < 0.001
249 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.19 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
C3	0.6401 (3)	0.7090 (3)	0.22861 (16)	0.0471 (6)
C9	0.5822 (4)	0.5897 (3)	0.14510 (18)	0.0607 (7)
H9	0.4806	0.5923	0.0939	0.073*
C8	0.6736 (5)	0.4706 (3)	0.1386 (2)	0.0673 (8)
H8	0.6315	0.3934	0.0830	0.081*
C7	0.8257 (5)	0.4609 (3)	0.2116 (2)	0.0668 (8)
H7	0.8853	0.3786	0.2060	0.080*
C6	0.8875 (4)	0.5768 (3)	0.2933 (2)	0.0603 (7)
H6	0.9899	0.5722	0.3435	0.072*
C4	0.7999 (3)	0.6994 (2)	0.30189 (17)	0.0471 (6)
C5	0.8865 (4)	0.8247 (3)	0.38437 (17)	0.0455 (6)
C2	0.5670 (4)	0.9219 (3)	0.34314 (17)	0.0488 (6)
H2	0.4847	0.8770	0.3746	0.059*
C10	0.4953 (4)	1.0622 (2)	0.35316 (17)	0.0471 (6)
C11	0.6035 (4)	1.1584 (3)	0.3306 (2)	0.0582 (7)
H11	0.7229	1.1350	0.3076	0.070*
C12	0.5398 (4)	1.2879 (3)	0.3413 (2)	0.0606 (7)
H12	0.6149	1.3507	0.3253	0.073*
C13	0.3628 (4)	1.3234 (3)	0.37595 (19)	0.0531 (7)
C14	0.2530 (4)	1.2271 (3)	0.39750 (19)	0.0590 (7)
H14	0.1326	1.2494	0.4197	0.071*
C15	0.3190 (4)	1.1000 (3)	0.38660 (18)	0.0532 (7)
H15	0.2430	1.0371	0.4021	0.064*
C16	0.3829 (3)	0.8424 (3)	0.16797 (17)	0.0526 (7)
H16A	0.4108	0.7956	0.1030	0.063*
H16B	0.3718	0.9387	0.1751	0.063*
C17	0.1780 (4)	0.7821 (3)	0.1740 (2)	0.0608 (7)
H17A	0.1827	0.6840	0.1617	0.073*
H17B	0.1500	0.8250	0.2395	0.073*
C18	0.0121 (4)	0.8067 (3)	0.09942 (19)	0.0558 (7)
C19	−0.0737 (5)	0.9296 (4)	0.1175 (3)	0.0862 (10)
H19	−0.0335	0.9977	0.1787	0.103*
C20	−0.2176 (6)	0.9556 (5)	0.0480 (4)	0.1082 (13)
H20	−0.2743	1.0400	0.0624	0.130*
C21	−0.2768 (5)	0.8570 (6)	−0.0423 (4)	0.1016 (13)
H21	−0.3730	0.8741	−0.0900	0.122*
C22	−0.1950 (5)	0.7345 (5)	−0.0621 (2)	0.0909 (11)
H22	−0.2361	0.6670	−0.1234	0.109*
C23	−0.0509 (4)	0.7087 (3)	0.0078 (2)	0.0705 (8)
H23	0.0046	0.6239	−0.0071	0.085*
C24	0.4088 (5)	1.5535 (3)	0.3750 (3)	0.0771 (9)
H24A	0.5424	1.5668	0.4145	0.116*
H24B	0.3445	1.6385	0.3921	0.116*
H24C	0.4180	1.5245	0.3068	0.116*
N2	0.5545 (3)	0.8327 (2)	0.24043 (13)	0.0472 (5)
N1	0.7792 (3)	0.9342 (2)	0.39205 (16)	0.0495 (6)
O2	1.0521 (3)	0.82989 (18)	0.43813 (13)	0.0608 (5)
O1	0.2907 (3)	1.4496 (2)	0.39241 (16)	0.0740 (6)
H1N	0.811 (4)	1.004 (3)	0.437 (2)	0.057 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C3	0.0442 (13)	0.0537 (15)	0.0388 (13)	−0.0104 (11)	0.0054 (11)	0.0115 (11)
C9	0.0639 (17)	0.0640 (19)	0.0409 (14)	−0.0093 (14)	0.0017 (12)	0.0053 (13)
C8	0.0723 (19)	0.0572 (18)	0.0552 (17)	−0.0106 (15)	0.0129 (15)	−0.0032 (14)
C7	0.0670 (18)	0.0509 (17)	0.075 (2)	0.0005 (13)	0.0158 (16)	0.0101 (14)
C6	0.0522 (15)	0.0568 (17)	0.0658 (18)	−0.0040 (13)	0.0046 (13)	0.0165 (14)
C4	0.0430 (13)	0.0471 (15)	0.0474 (14)	−0.0082 (11)	0.0056 (11)	0.0128 (11)
C5	0.0414 (13)	0.0478 (15)	0.0431 (14)	−0.0087 (11)	−0.0005 (11)	0.0149 (11)
C2	0.0465 (14)	0.0550 (16)	0.0408 (13)	−0.0100 (11)	0.0016 (11)	0.0147 (11)
C10	0.0434 (14)	0.0506 (15)	0.0411 (13)	−0.0076 (11)	−0.0045 (11)	0.0144 (11)
C11	0.0434 (14)	0.0659 (18)	0.0659 (17)	0.0009 (13)	0.0157 (12)	0.0205 (14)
C12	0.0585 (17)	0.0589 (18)	0.0694 (18)	−0.0070 (13)	0.0139 (14)	0.0281 (14)
C13	0.0459 (15)	0.0534 (16)	0.0581 (16)	0.0047 (12)	0.0009 (12)	0.0210 (13)
C14	0.0443 (14)	0.0666 (19)	0.0617 (17)	−0.0021 (13)	0.0126 (12)	0.0152 (14)
C15	0.0516 (15)	0.0552 (17)	0.0504 (15)	−0.0128 (12)	0.0046 (12)	0.0182 (12)
C16	0.0476 (14)	0.0669 (17)	0.0392 (13)	−0.0109 (12)	−0.0029 (11)	0.0191 (12)
C17	0.0507 (15)	0.0780 (19)	0.0507 (15)	−0.0147 (13)	−0.0005 (12)	0.0238 (13)
C18	0.0389 (13)	0.0719 (19)	0.0534 (16)	−0.0091 (13)	0.0054 (12)	0.0191 (14)
C19	0.0595 (19)	0.093 (3)	0.090 (2)	0.0107 (18)	0.0126 (18)	0.010 (2)
C20	0.063 (2)	0.117 (3)	0.153 (4)	0.026 (2)	0.020 (3)	0.058 (3)
C21	0.0457 (19)	0.160 (4)	0.113 (3)	0.001 (2)	−0.006 (2)	0.075 (3)
C22	0.058 (2)	0.133 (3)	0.066 (2)	−0.021 (2)	−0.0151 (17)	0.028 (2)
C23	0.0527 (16)	0.079 (2)	0.0646 (18)	−0.0123 (14)	−0.0085 (14)	0.0155 (15)
C24	0.075 (2)	0.0611 (19)	0.093 (2)	−0.0070 (15)	0.0100 (17)	0.0263 (16)
N2	0.0452 (11)	0.0542 (13)	0.0349 (11)	−0.0064 (9)	−0.0037 (9)	0.0118 (9)
N1	0.0474 (12)	0.0457 (13)	0.0419 (12)	−0.0068 (10)	−0.0091 (9)	0.0065 (10)
O2	0.0468 (10)	0.0582 (12)	0.0611 (11)	−0.0057 (8)	−0.0139 (9)	0.0114 (9)
O1	0.0629 (12)	0.0635 (13)	0.1001 (16)	0.0077 (10)	0.0174 (11)	0.0327 (11)

Geometric parameters (Å, º)

C3—N2	1.379 (3)	C14—C15	1.358 (3)
C3—C4	1.409 (3)	C14—H14	0.9300
C3—C9	1.411 (3)	C15—H15	0.9300
C9—C8	1.365 (4)	C16—N2	1.453 (3)
C9—H9	0.9300	C16—C17	1.532 (3)
C8—C7	1.374 (4)	C16—H16A	0.9700
C8—H8	0.9300	C16—H16B	0.9700
C7—C6	1.380 (4)	C17—C18	1.506 (4)
C7—H7	0.9300	C17—H17A	0.9700
C6—C4	1.381 (3)	C17—H17B	0.9700
C6—H6	0.9300	C18—C19	1.366 (4)
C4—C5	1.474 (3)	C18—C23	1.378 (4)
C5—O2	1.234 (3)	C19—C20	1.375 (5)
C5—N1	1.333 (3)	C19—H19	0.9300
C2—N1	1.462 (3)	C20—C21	1.365 (6)
C2—N2	1.472 (3)	C20—H20	0.9300
C2—C10	1.502 (3)	C21—C22	1.348 (5)
C2—H2	0.9800	C21—H21	0.9300
C10—C15	1.375 (4)	C22—C23	1.377 (4)
C10—C11	1.381 (3)	C22—H22	0.9300
C11—C12	1.378 (4)	C23—H23	0.9300
C11—H11	0.9300	C24—O1	1.441 (3)
C12—C13	1.383 (4)	C24—H24A	0.9600
C12—H12	0.9300	C24—H24B	0.9600
C13—O1	1.358 (3)	C24—H24C	0.9600
C13—C14	1.380 (4)	N1—H1N	0.79 (3)
N2—C3—C4	119.3 (2)	C10—C15—H15	119.2
N2—C3—C9	124.0 (2)	N2—C16—C17	115.5 (2)
C4—C3—C9	116.7 (2)	N2—C16—H16A	108.4
C8—C9—C3	120.7 (3)	C17—C16—H16A	108.4
C8—C9—H9	119.6	N2—C16—H16B	108.4
C3—C9—H9	119.6	C17—C16—H16B	108.4
C9—C8—C7	122.3 (2)	H16A—C16—H16B	107.5
C9—C8—H8	118.9	C18—C17—C16	110.1 (2)
C7—C8—H8	118.9	C18—C17—H17A	109.6
C8—C7—C6	118.1 (3)	C16—C17—H17A	109.6
C8—C7—H7	120.9	C18—C17—H17B	109.6
C6—C7—H7	120.9	C16—C17—H17B	109.6
C7—C6—C4	121.2 (3)	H17A—C17—H17B	108.2
C7—C6—H6	119.4	C19—C18—C23	117.2 (3)
C4—C6—H6	119.4	C19—C18—C17	121.5 (3)
C6—C4—C3	120.9 (2)	C23—C18—C17	121.2 (3)
C6—C4—C5	119.4 (2)	C18—C19—C20	121.9 (3)
C3—C4—C5	119.4 (2)	C18—C19—H19	119.0
O2—C5—N1	122.7 (2)	C20—C19—H19	119.0
O2—C5—C4	122.3 (2)	C21—C20—C19	119.6 (4)
N1—C5—C4	114.8 (2)	C21—C20—H20	120.2
N1—C2—N2	106.9 (2)	C19—C20—H20	120.2
N1—C2—C10	110.06 (19)	C22—C21—C20	119.7 (4)
N2—C2—C10	113.43 (19)	C22—C21—H21	120.2
N1—C2—H2	108.8	C20—C21—H21	120.2
N2—C2—H2	108.8	C21—C22—C23	120.6 (3)
C10—C2—H2	108.8	C21—C22—H22	119.7
C15—C10—C11	117.5 (2)	C23—C22—H22	119.7
C15—C10—C2	120.7 (2)	C22—C23—C18	121.0 (3)
C11—C10—C2	121.8 (2)	C22—C23—H23	119.5
C12—C11—C10	121.9 (2)	C18—C23—H23	119.5
C12—C11—H11	119.0	O1—C24—H24A	109.5
C10—C11—H11	119.0	O1—C24—H24B	109.5
C11—C12—C13	119.2 (2)	H24A—C24—H24B	109.5
C11—C12—H12	120.4	O1—C24—H24C	109.5
C13—C12—H12	120.4	H24A—C24—H24C	109.5
O1—C13—C14	117.1 (2)	H24B—C24—H24C	109.5
O1—C13—C12	123.9 (2)	C3—N2—C16	119.91 (19)
C14—C13—C12	119.0 (2)	C3—N2—C2	114.97 (18)
C15—C14—C13	120.7 (2)	C16—N2—C2	117.8 (2)
C15—C14—H14	119.6	C5—N1—C2	122.1 (2)
C13—C14—H14	119.6	C5—N1—H1N	121 (2)
C14—C15—C10	121.6 (2)	C2—N1—H1N	114 (2)
C14—C15—H15	119.2	C13—O1—C24	117.9 (2)
N2—C3—C9—C8	−179.8 (2)	C2—C10—C15—C14	179.0 (2)
C4—C3—C9—C8	2.2 (4)	N2—C16—C17—C18	176.5 (2)
C3—C9—C8—C7	−0.6 (4)	C16—C17—C18—C19	−81.9 (3)
C9—C8—C7—C6	−0.5 (4)	C16—C17—C18—C23	94.2 (3)
C8—C7—C6—C4	−0.2 (4)	C23—C18—C19—C20	0.2 (5)
C7—C6—C4—C3	1.9 (4)	C17—C18—C19—C20	176.5 (3)
C7—C6—C4—C5	−172.6 (2)	C18—C19—C20—C21	−0.5 (6)
N2—C3—C4—C6	179.1 (2)	C19—C20—C21—C22	0.6 (6)
C9—C3—C4—C6	−2.9 (3)	C20—C21—C22—C23	−0.6 (5)
N2—C3—C4—C5	−6.3 (3)	C21—C22—C23—C18	0.4 (5)
C9—C3—C4—C5	171.7 (2)	C19—C18—C23—C22	−0.2 (4)
C6—C4—C5—O2	11.1 (3)	C17—C18—C23—C22	−176.4 (3)
C3—C4—C5—O2	−163.6 (2)	C4—C3—N2—C16	−176.9 (2)
C6—C4—C5—N1	−173.3 (2)	C9—C3—N2—C16	5.2 (3)
C3—C4—C5—N1	12.0 (3)	C4—C3—N2—C2	−27.4 (3)
N1—C2—C10—C15	−129.3 (2)	C9—C3—N2—C2	154.7 (2)
N2—C2—C10—C15	111.0 (2)	C17—C16—N2—C3	77.0 (3)
N1—C2—C10—C11	49.9 (3)	C17—C16—N2—C2	−71.6 (3)
N2—C2—C10—C11	−69.9 (3)	N1—C2—N2—C3	51.5 (2)
C15—C10—C11—C12	0.3 (4)	C10—C2—N2—C3	173.01 (18)
C2—C10—C11—C12	−178.9 (2)	N1—C2—N2—C16	−158.36 (19)
C10—C11—C12—C13	0.3 (4)	C10—C2—N2—C16	−36.8 (3)
C11—C12—C13—O1	177.5 (2)	O2—C5—N1—C2	−166.9 (2)
C11—C12—C13—C14	−1.0 (4)	C4—C5—N1—C2	17.6 (3)
O1—C13—C14—C15	−177.5 (2)	N2—C2—N1—C5	−48.4 (3)
C12—C13—C14—C15	1.1 (4)	C10—C2—N1—C5	−172.0 (2)
C13—C14—C15—C10	−0.5 (4)	C14—C13—O1—C24	176.9 (2)
C11—C10—C15—C14	−0.2 (3)	C12—C13—O1—C24	−1.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2^i	0.79 (3)	2.11 (3)	2.888 (3)	169 (3)
C6—H6···O1^ii	0.93	2.52	3.340 (4)	147
C24—H24C···Cg1^iii	0.96	2.83	3.513	129

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

(II) (±)-2-(1,3-benzodioxol-5-yl))-1-phenethyl-2,3-dihydroquinazolin-4(1H)-one

Crystal data

C23H20N2O3	F(000) = 1568
Mr = 372.41	Dx = 1.286 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yc	Cell parameters from 3399 reflections
a = 29.840 (5) Å	θ = 2.9–21.2°
b = 6.6467 (10) Å	µ = 0.09 mm^−1
c = 20.587 (3) Å	T = 293 K
β = 109.529 (2)°	Prism, colourless
V = 3848.2 (10) Å^3	0.22 × 0.18 × 0.16 mm
Z = 8

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2799 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Graphite monochromator	θmax = 25.0°, θmin = 1.5°
ω scans	h = −35→35
17515 measured reflections	k = −7→7
3385 independent reflections	l = −24→24

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)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.194	H atoms treated by a mixture of independent and constrained refinement
S = 1.28	w = 1/[σ^2(Fo^2) + (0.0691P)^2 + 3.2484P] where P = (Fo^2 + 2Fc^2)/3
3385 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.15 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	0.92222 (10)	0.1328 (5)	0.95648 (14)	0.0489 (7)
H2	0.9353	0.0379	0.9946	0.059*
C3	0.86386 (10)	0.2605 (5)	1.00245 (15)	0.0475 (7)
C4	0.89882 (10)	0.3902 (5)	1.04433 (14)	0.0480 (7)
C5	0.94058 (10)	0.4406 (5)	1.02503 (14)	0.0449 (7)
C6	0.89215 (12)	0.4860 (5)	1.10022 (17)	0.0614 (9)
H6	0.9160	0.5691	1.1280	0.074*
C7	0.85109 (13)	0.4605 (6)	1.1154 (2)	0.0731 (10)
H7	0.8470	0.5245	1.1532	0.088*
C8	0.81613 (13)	0.3376 (6)	1.0734 (2)	0.0753 (11)
H8	0.7880	0.3203	1.0829	0.090*
C9	0.82181 (11)	0.2399 (6)	1.01775 (18)	0.0640 (9)
H9	0.7974	0.1594	0.9900	0.077*
C10	0.93007 (10)	0.0484 (5)	0.89291 (14)	0.0471 (7)
C11	0.91799 (11)	0.1644 (5)	0.83271 (16)	0.0543 (8)
H11	0.9058	0.2939	0.8309	0.065*
C12	0.92496 (11)	0.0776 (5)	0.77686 (15)	0.0553 (8)
C13	0.94326 (11)	−0.1127 (5)	0.77858 (16)	0.0569 (8)
C14	0.95551 (12)	−0.2262 (5)	0.83675 (19)	0.0668 (10)
H14	0.9681	−0.3547	0.8381	0.080*
C15	0.94830 (11)	−0.1415 (5)	0.89411 (17)	0.0566 (8)
H15	0.9561	−0.2159	0.9346	0.068*
C16	0.83723 (10)	0.0217 (5)	0.90627 (15)	0.0523 (8)
H16A	0.8428	0.0024	0.8629	0.063*
H16B	0.8057	0.0789	0.8958	0.063*
C17	0.83770 (12)	−0.1848 (5)	0.93947 (18)	0.0637 (9)
H17A	0.8684	−0.2480	0.9481	0.076*
H17B	0.8326	−0.1688	0.9833	0.076*
C18	0.79945 (12)	−0.3156 (5)	0.89282 (17)	0.0554 (8)
C19	0.80755 (18)	−0.4376 (6)	0.8443 (2)	0.0854 (12)
H19	0.8380	−0.4455	0.8414	0.102*
C23	0.75382 (13)	−0.3090 (6)	0.8948 (2)	0.0733 (10)
H23	0.7473	−0.2274	0.9272	0.088*
C22	0.71790 (17)	−0.4187 (8)	0.8505 (3)	0.1015 (15)
H22	0.6874	−0.4105	0.8531	0.122*
C21	0.7262 (3)	−0.5380 (8)	0.8035 (3)	0.116 (2)
H21	0.7014	−0.6127	0.7738	0.139*
C20	0.7705 (3)	−0.5515 (7)	0.7986 (2)	0.1135 (19)
H20	0.7762	−0.6342	0.7658	0.136*
C24	0.92890 (16)	0.0084 (7)	0.67328 (19)	0.0872 (13)
H24A	0.9530	0.0603	0.6558	0.105*
H24B	0.9014	−0.0302	0.6343	0.105*
N1	0.94653 (9)	0.3247 (4)	0.97546 (12)	0.0492 (7)
N2	0.87174 (8)	0.1671 (4)	0.94720 (12)	0.0487 (6)
O1	0.91591 (11)	0.1580 (4)	0.71250 (12)	0.0875 (9)
O2	0.96678 (7)	0.5842 (3)	1.05047 (11)	0.0600 (6)
O3	0.94671 (10)	−0.1605 (4)	0.71592 (13)	0.0846 (8)
H1N	0.9722 (11)	0.342 (4)	0.9645 (15)	0.049 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0455 (17)	0.0562 (18)	0.0412 (16)	−0.0062 (14)	0.0095 (13)	0.0099 (14)
C3	0.0415 (16)	0.0542 (18)	0.0447 (16)	−0.0010 (14)	0.0114 (13)	0.0122 (14)
C4	0.0476 (17)	0.0530 (18)	0.0428 (16)	0.0001 (14)	0.0144 (13)	0.0109 (14)
C5	0.0405 (15)	0.0529 (18)	0.0373 (15)	−0.0075 (14)	0.0076 (12)	0.0083 (14)
C6	0.061 (2)	0.068 (2)	0.057 (2)	−0.0069 (17)	0.0223 (17)	−0.0005 (17)
C7	0.074 (2)	0.086 (3)	0.071 (2)	−0.002 (2)	0.040 (2)	−0.004 (2)
C8	0.057 (2)	0.092 (3)	0.087 (3)	0.002 (2)	0.038 (2)	0.009 (2)
C9	0.0435 (18)	0.078 (2)	0.070 (2)	−0.0069 (17)	0.0178 (16)	0.0047 (19)
C10	0.0420 (16)	0.0526 (18)	0.0424 (16)	−0.0075 (14)	0.0083 (13)	0.0043 (14)
C11	0.0600 (19)	0.0479 (18)	0.0541 (19)	0.0065 (15)	0.0178 (15)	0.0037 (15)
C12	0.0565 (19)	0.062 (2)	0.0451 (17)	0.0026 (16)	0.0142 (15)	0.0026 (16)
C13	0.0515 (18)	0.062 (2)	0.0525 (19)	0.0035 (16)	0.0112 (15)	−0.0059 (17)
C14	0.064 (2)	0.055 (2)	0.078 (3)	0.0130 (17)	0.0198 (19)	0.0050 (19)
C15	0.0490 (18)	0.060 (2)	0.0568 (19)	0.0029 (15)	0.0120 (15)	0.0123 (16)
C16	0.0427 (16)	0.0555 (19)	0.0499 (18)	−0.0071 (14)	0.0038 (13)	0.0066 (15)
C17	0.0533 (19)	0.063 (2)	0.066 (2)	−0.0085 (16)	0.0089 (16)	0.0135 (17)
C18	0.062 (2)	0.0446 (18)	0.0584 (19)	−0.0044 (15)	0.0180 (16)	0.0095 (15)
C19	0.112 (3)	0.060 (2)	0.092 (3)	0.019 (2)	0.045 (3)	0.011 (2)
C23	0.068 (2)	0.070 (2)	0.083 (3)	−0.020 (2)	0.028 (2)	−0.002 (2)
C22	0.083 (3)	0.089 (3)	0.117 (4)	−0.038 (3)	0.013 (3)	0.010 (3)
C21	0.158 (6)	0.066 (3)	0.090 (4)	−0.040 (4)	−0.004 (4)	0.006 (3)
C20	0.203 (6)	0.055 (3)	0.079 (3)	0.002 (4)	0.041 (4)	−0.010 (2)
C24	0.096 (3)	0.112 (4)	0.053 (2)	0.022 (3)	0.024 (2)	−0.007 (2)
N1	0.0402 (14)	0.0657 (17)	0.0424 (14)	−0.0120 (13)	0.0148 (11)	0.0009 (12)
N2	0.0355 (13)	0.0586 (16)	0.0473 (14)	−0.0075 (11)	0.0076 (11)	0.0032 (12)
O1	0.122 (2)	0.094 (2)	0.0490 (14)	0.0310 (17)	0.0326 (14)	0.0138 (13)
O2	0.0564 (13)	0.0695 (15)	0.0562 (13)	−0.0239 (12)	0.0217 (10)	−0.0103 (11)
O3	0.0932 (19)	0.094 (2)	0.0618 (16)	0.0212 (16)	0.0201 (14)	−0.0154 (15)

Geometric parameters (Å, º)

C2—N1	1.455 (4)	C14—C15	1.389 (5)
C2—N2	1.471 (4)	C14—H14	0.9300
C2—C10	1.512 (4)	C15—H15	0.9300
C2—H2	0.9800	C16—N2	1.458 (4)
C3—N2	1.383 (4)	C16—C17	1.531 (4)
C3—C9	1.398 (4)	C16—H16A	0.9700
C3—C4	1.405 (4)	C16—H16B	0.9700
C4—C6	1.386 (4)	C17—C18	1.499 (4)
C4—C5	1.468 (4)	C17—H17A	0.9700
C5—O2	1.234 (3)	C17—H17B	0.9700
C5—N1	1.337 (4)	C18—C19	1.370 (5)
C6—C7	1.372 (5)	C18—C23	1.377 (5)
C6—H6	0.9300	C19—C20	1.408 (7)
C7—C8	1.379 (5)	C19—H19	0.9300
C7—H7	0.9300	C23—C22	1.363 (5)
C8—C9	1.375 (5)	C23—H23	0.9300
C8—H8	0.9300	C22—C21	1.336 (7)
C9—H9	0.9300	C22—H22	0.9300
C10—C15	1.372 (4)	C21—C20	1.362 (8)
C10—C11	1.400 (4)	C21—H21	0.9300
C11—C12	1.363 (4)	C20—H20	0.9300
C11—H11	0.9300	C24—O1	1.414 (4)
C12—O1	1.369 (4)	C24—O3	1.415 (5)
C12—C13	1.374 (5)	C24—H24A	0.9700
C13—C14	1.358 (5)	C24—H24B	0.9700
C13—O3	1.365 (4)	N1—H1N	0.88 (3)
N1—C2—N2	107.2 (2)	N2—C16—C17	115.9 (2)
N1—C2—C10	110.5 (2)	N2—C16—H16A	108.3
N2—C2—C10	113.1 (2)	C17—C16—H16A	108.3
N1—C2—H2	108.6	N2—C16—H16B	108.3
N2—C2—H2	108.6	C17—C16—H16B	108.3
C10—C2—H2	108.6	H16A—C16—H16B	107.4
N2—C3—C9	123.6 (3)	C18—C17—C16	110.0 (3)
N2—C3—C4	119.0 (3)	C18—C17—H17A	109.7
C9—C3—C4	117.4 (3)	C16—C17—H17A	109.7
C6—C4—C3	120.5 (3)	C18—C17—H17B	109.7
C6—C4—C5	119.4 (3)	C16—C17—H17B	109.7
C3—C4—C5	119.8 (3)	H17A—C17—H17B	108.2
O2—C5—N1	122.9 (3)	C19—C18—C23	117.2 (4)
O2—C5—C4	122.4 (3)	C19—C18—C17	121.9 (4)
N1—C5—C4	114.6 (3)	C23—C18—C17	120.7 (3)
C7—C6—C4	121.3 (3)	C18—C19—C20	121.0 (5)
C7—C6—H6	119.4	C18—C19—H19	119.5
C4—C6—H6	119.4	C20—C19—H19	119.5
C6—C7—C8	118.4 (3)	C22—C23—C18	121.9 (4)
C6—C7—H7	120.8	C22—C23—H23	119.1
C8—C7—H7	120.8	C18—C23—H23	119.1
C9—C8—C7	121.6 (3)	C21—C22—C23	120.5 (5)
C9—C8—H8	119.2	C21—C22—H22	119.8
C7—C8—H8	119.2	C23—C22—H22	119.8
C8—C9—C3	120.7 (3)	C22—C21—C20	120.8 (5)
C8—C9—H9	119.6	C22—C21—H21	119.6
C3—C9—H9	119.6	C20—C21—H21	119.6
C15—C10—C11	120.4 (3)	C21—C20—C19	118.7 (5)
C15—C10—C2	120.1 (3)	C21—C20—H20	120.7
C11—C10—C2	119.6 (3)	C19—C20—H20	120.7
C12—C11—C10	116.5 (3)	O1—C24—O3	108.8 (3)
C12—C11—H11	121.7	O1—C24—H24A	109.9
C10—C11—H11	121.7	O3—C24—H24A	109.9
C11—C12—O1	127.9 (3)	O1—C24—H24B	109.9
C11—C12—C13	122.6 (3)	O3—C24—H24B	109.9
O1—C12—C13	109.4 (3)	H24A—C24—H24B	108.3
C14—C13—O3	128.4 (3)	C5—N1—C2	121.9 (3)
C14—C13—C12	121.5 (3)	C5—N1—H1N	118 (2)
O3—C13—C12	110.2 (3)	C2—N1—H1N	117 (2)
C13—C14—C15	116.9 (3)	C3—N2—C16	119.4 (2)
C13—C14—H14	121.6	C3—N2—C2	114.3 (2)
C15—C14—H14	121.6	C16—N2—C2	117.8 (2)
C10—C15—C14	122.1 (3)	C12—O1—C24	106.0 (3)
C10—C15—H15	119.0	C13—O3—C24	105.7 (3)
C14—C15—H15	119.0
N2—C3—C4—C6	−179.9 (3)	N2—C16—C17—C18	178.1 (3)
C9—C3—C4—C6	2.8 (4)	C16—C17—C18—C19	90.1 (4)
N2—C3—C4—C5	6.2 (4)	C16—C17—C18—C23	−86.3 (4)
C9—C3—C4—C5	−171.2 (3)	C23—C18—C19—C20	−0.1 (5)
C6—C4—C5—O2	−10.1 (4)	C17—C18—C19—C20	−176.7 (3)
C3—C4—C5—O2	163.9 (3)	C19—C18—C23—C22	0.0 (5)
C6—C4—C5—N1	173.0 (3)	C17—C18—C23—C22	176.6 (3)
C3—C4—C5—N1	−13.0 (4)	C18—C23—C22—C21	0.3 (7)
C3—C4—C6—C7	−1.4 (5)	C23—C22—C21—C20	−0.4 (8)
C5—C4—C6—C7	172.6 (3)	C22—C21—C20—C19	0.2 (8)
C4—C6—C7—C8	−0.4 (5)	C18—C19—C20—C21	0.0 (7)
C6—C7—C8—C9	0.7 (6)	O2—C5—N1—C2	166.6 (3)
C7—C8—C9—C3	0.8 (6)	C4—C5—N1—C2	−16.5 (4)
N2—C3—C9—C8	−179.7 (3)	N2—C2—N1—C5	48.4 (3)
C4—C3—C9—C8	−2.5 (5)	C10—C2—N1—C5	172.1 (3)
N1—C2—C10—C15	125.2 (3)	C9—C3—N2—C16	−7.0 (4)
N2—C2—C10—C15	−114.6 (3)	C4—C3—N2—C16	175.8 (2)
N1—C2—C10—C11	−55.7 (3)	C9—C3—N2—C2	−154.4 (3)
N2—C2—C10—C11	64.5 (3)	C4—C3—N2—C2	28.4 (4)
C15—C10—C11—C12	0.6 (4)	C17—C16—N2—C3	−75.1 (4)
C2—C10—C11—C12	−178.5 (3)	C17—C16—N2—C2	71.1 (4)
C10—C11—C12—O1	179.7 (3)	N1—C2—N2—C3	−52.6 (3)
C10—C11—C12—C13	−0.6 (5)	C10—C2—N2—C3	−174.6 (2)
C11—C12—C13—C14	0.1 (5)	N1—C2—N2—C16	159.5 (2)
O1—C12—C13—C14	179.8 (3)	C10—C2—N2—C16	37.4 (3)
C11—C12—C13—O3	−179.5 (3)	C11—C12—O1—C24	−179.7 (4)
O1—C12—C13—O3	0.2 (4)	C13—C12—O1—C24	0.6 (4)
O3—C13—C14—C15	−180.0 (3)	O3—C24—O1—C12	−1.2 (4)
C12—C13—C14—C15	0.5 (5)	C14—C13—O3—C24	179.5 (4)
C11—C10—C15—C14	0.0 (5)	C12—C13—O3—C24	−0.9 (4)
C2—C10—C15—C14	179.1 (3)	O1—C24—O3—C13	1.3 (4)
C13—C14—C15—C10	−0.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2^i	0.88 (3)	2.01 (3)	2.875 (3)	171 (3)
C6—H6···O1^ii	0.93	2.51	3.217 (4)	133
C20—H20···Cg1^iii	0.93	2.96	3.783	148
C24—H24A···Cg2^iv	0.97	2.77	3.580	142

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