2-Methyl-3-(2-methyl­phen­yl)-4-oxo-3,4-dihydro­quinazolin-8-yl benzoate

El-Azab, A.S.; Abdel-Aziz, A.A.-M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812006253

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o732-o733

doi:10.1107/S1600536812006253

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2-Methyl-3-(2-methylphenyl)-4-oxo-3,4-dihydroquinazolin-8-yl benzoate

Adel S. El-Azab,^a,^b ‡ Alaa A.-M. Abdel-Aziz,^a,^c Seik Weng Ng ^d,^e and Edward R. T. Tiekink ^d ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt, ^cDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt, ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^eChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 12 February 2012; accepted 12 February 2012; online 17 February 2012)

In the title quinazolin-4-one derivative, C₂₃H₁₈N₂O₃, both the benzoate [dihedral angle = 79.99 (6)°] and the 2-tolyl [89.02 (7)°] groups are close to orthogonal to the central fused ring system. Both aryl groups are orientated towards the quinazolin-4-one-bound methyl group. In the crystal, molecules are connected into a three-dimensional architecture by C—H⋯O, C—H⋯N and C—H⋯π interactions.

Related literature

For the pharmacological activity of substituted quinazoline-4(3H)-ones, see: El-Azab & El-Tahir (2012 ); El-Azab et al. (2011 ); Al-Omary et al. (2010 ); Al-Obaid et al. (2009 ); Aziza et al. (1996 ). For the synthesis and evaluation of the anti-convulsant activity of the title compound, see: El-Azab et al. (2010 ). For the structure of the benzoate derivative, see: El-Azab et al. (2012 ).

Experimental

Crystal data

C₂₃H₁₈N₂O₃
M_r = 370.39
Monoclinic, P 2₁ /c
a = 20.3847 (4) Å
b = 7.4352 (1) Å
c = 12.7829 (3) Å
β = 107.489 (2)°
V = 1847.87 (6) Å³
Z = 4
Cu Kα radiation
μ = 0.72 mm⁻¹
T = 100 K
0.30 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.470, T_max = 1.000
7377 measured reflections
3780 independent reflections
3432 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.132
S = 1.05
3780 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C17–C22 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1ⁱ	0.95	2.58	3.521 (2)	172
C16—H16c⋯O2ⁱⁱ	0.98	2.44	3.298 (2)	146
C20—H20⋯O3ⁱⁱⁱ	0.95	2.59	3.225 (2)	124
C11—H11⋯Cg1^iv	0.95	2.72	3.5519 (18)	147
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x, y+1, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006253/hb6635sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006253/hb6635Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006253/hb6635Isup3.cml

checkCIF report

Comment top

Substituted quinazoline-4(3H)-ones are known to display various biological activities (El-Azab & El-Tahir, 2012; El-Azab et al., 2011; El-Azab et al., 2010; Al-Omary et al., 2010; Al-Obaid et al., 2009; Aziza et al., 1996). The title compound, 3,4-dihydro-2-methyl-3-(2-methylphenyl)-4-oxoquinazolin-8-yl benzoate (I), a methaqualone analogue, was recently synthesized and evaluated for its anti-convulsant activity (El-Azab et al., 2010). Herein, the crystal structure determination of (I) is reported.

In (I), Fig. 1, the carboxylate residue is co-planar to the benzene ring to which it is connected as seen in the value of the C2—C1—C7—O1 torsion angle -4.3 (2)°. With respect to the central quinazolin-4-one fused ring system [r.m.s. deviation = 0.035 Å for the 10 atoms], both the benzoate and 2-tolyl groups are orthogonal: the dihedral angles between the central plane and six-membered rings being 79.99 (6) and 89.02 (7)°, respectively. Both aryl substituents are orientated towards the methyl group bound to the quinazolin-4-one system, and the dihedral angle between the two six-membered rings is 64.23 (8)°. The molecular structure resembles closely that of the p-tolyl benzoate derivative (El-Azab et al., 2012).

In the crystal packing, C—H···N [involving the quinazolin-N atom], C—H···O [involving both carbonyl-O atoms] and C—H···π [involving the (C17···C22) benzene ring] interactions are formed, Table 1. These lead to a three-dimensional architecture, Fig. 2.

Related literature top

For the pharmacological activity of substituted quinazoline-4(3H)-ones, see: El-Azab & El-Tahir (2012); El-Azab et al. (2011); Al-Omary et al. (2010); Al-Obaid et al. (2009); Aziza et al. (1996). For the synthesis and evaluation of the anti-convulsant activity of the title compound, see: El-Azab et al. (2010). For the structure of the benzoate derivative, see: El-Azab et al. (2012).

Experimental top

A mixture of 8-hydroxymethaqualone (532 mg, 0.002 M) and benzoyl chloride (296 mg, 0.0021 M) in 15 ml pyridine was stirred at room temperature for 11 h. The solvent was removed under reduced pressure, and the residue was triturated with water and filtered. The solid obtained was dried and recrystallized from EtOH to yield colourless prisms. M.pt.: 438–440. Yield: 94%.

¹H NMR (500 MHz, CDCl₃): δ = 8.21 (d, 2H, J = 7.5 Hz), 8.09 (d, 1H, J = 8.0 Hz), 7.82 (d, 1H, J = 8.0 Hz), 7.78 (t, 1H, J = 7.5 Hz), 7.65–7.58 (m, 3H), 7.46–7.38 (m, 4H), 2.04 (s, 3H), 1.99 (s, 3H) p.p.m.. ¹³C NMR (CDCl₃): δ = 17.3, 24.5, 122.3, 124.7, 127.0, 127.9, 128.2, 128.8, 129.3, 129.5, 129.9, 130.4, 131.6, 134.5, 135.5, 137.1, 140.9, 146.2, 155.5, 160.7, 165.0 p.p.m.. MS (70 eV): m/z = 370.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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 DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view in projection down the b axis of the unit-cell contents for (I). The C—H···O, C—H···N and C—H···π interactions are shown as orange, blue and purple dashed lines, respectively.

2-Methyl-3-(2-methylphenyl)-4-oxo-3,4-dihydroquinazolin-8-yl benzoate top

Crystal data top

C₂₃H₁₈N₂O₃	F(000) = 776
M_r = 370.39	D_x = 1.331 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 4141 reflections
a = 20.3847 (4) Å	θ = 3.6–76.0°
b = 7.4352 (1) Å	µ = 0.72 mm⁻¹
c = 12.7829 (3) Å	T = 100 K
β = 107.489 (2)°	Prism, colourless
V = 1847.87 (6) Å³	0.30 × 0.10 × 0.05 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3780 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3432 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.015
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.1°, θ_min = 4.6°
ω scan	h = −22→25
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→6
T_min = 0.470, T_max = 1.000	l = −15→15
7377 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0621P)² + 1.4481P] where P = (F_o² + 2F_c²)/3
3780 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₃H₁₈N₂O₃	V = 1847.87 (6) Å³
M_r = 370.39	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 20.3847 (4) Å	µ = 0.72 mm⁻¹
b = 7.4352 (1) Å	T = 100 K
c = 12.7829 (3) Å	0.30 × 0.10 × 0.05 mm
β = 107.489 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3780 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3432 reflections with I > 2σ(I)
T_min = 0.470, T_max = 1.000	R_int = 0.015
7377 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.05	Δρ_max = 0.61 e Å⁻³
3780 reflections	Δρ_min = −0.28 e Å⁻³
255 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
O1	0.12153 (6)	0.28357 (15)	0.64163 (9)	0.0228 (3)
O2	0.17292 (6)	0.08881 (17)	0.55602 (10)	0.0287 (3)
O3	0.39006 (6)	0.65559 (18)	0.84640 (10)	0.0284 (3)
N1	0.21618 (7)	0.52042 (18)	0.60240 (11)	0.0197 (3)
N2	0.31826 (7)	0.69110 (19)	0.67202 (11)	0.0209 (3)
C1	0.05574 (8)	0.1737 (2)	0.46895 (13)	0.0220 (3)
C2	−0.00084 (9)	0.2669 (2)	0.48010 (14)	0.0248 (4)
H2	0.0028	0.3330	0.5452	0.030*
C3	−0.06272 (9)	0.2636 (2)	0.39634 (16)	0.0295 (4)
H3	−0.1014	0.3278	0.4038	0.035*
C4	−0.06782 (10)	0.1661 (2)	0.30169 (16)	0.0313 (4)
H4	−0.1101	0.1640	0.2443	0.038*
C5	−0.01162 (10)	0.0715 (2)	0.29002 (15)	0.0301 (4)
H5	−0.0156	0.0047	0.2251	0.036*
C6	0.05038 (9)	0.0750 (2)	0.37355 (14)	0.0258 (4)
H6	0.0890	0.0107	0.3660	0.031*
C7	0.12288 (8)	0.1733 (2)	0.55681 (13)	0.0212 (3)
C8	0.18435 (8)	0.3093 (2)	0.72251 (13)	0.0212 (3)
C9	0.19716 (9)	0.2213 (2)	0.82114 (14)	0.0248 (4)
H9	0.1646	0.1378	0.8323	0.030*
C10	0.25825 (9)	0.2546 (2)	0.90526 (14)	0.0254 (4)
H10	0.2674	0.1922	0.9730	0.030*
C11	0.30502 (9)	0.3773 (2)	0.89015 (13)	0.0225 (3)
H11	0.3466	0.3995	0.9470	0.027*
C12	0.29094 (8)	0.4695 (2)	0.79007 (13)	0.0195 (3)
C13	0.23106 (8)	0.4352 (2)	0.70379 (12)	0.0187 (3)
C14	0.33798 (8)	0.6088 (2)	0.77586 (13)	0.0205 (3)
C15	0.25920 (8)	0.6410 (2)	0.59004 (12)	0.0192 (3)
C16	0.24555 (9)	0.7342 (2)	0.48214 (13)	0.0238 (3)
H16A	0.2042	0.6836	0.4300	0.036*
H16B	0.2849	0.7174	0.4540	0.036*
H16C	0.2387	0.8629	0.4916	0.036*
C17	0.36264 (9)	0.8369 (2)	0.65716 (13)	0.0250 (4)
C18	0.35070 (9)	1.0096 (2)	0.69125 (15)	0.0276 (4)
H18	0.3126	1.0318	0.7177	0.033*
C19	0.39532 (9)	1.1478 (2)	0.68583 (15)	0.0303 (4)
H19	0.3875	1.2663	0.7071	0.036*
C20	0.45170 (9)	1.1116 (3)	0.64898 (14)	0.0290 (4)
H20	0.4829	1.2055	0.6469	0.035*
C21	0.46277 (9)	0.9408 (2)	0.61541 (14)	0.0269 (4)
H21	0.5012	0.9189	0.5898	0.032*
C22	0.41779 (9)	0.7985 (2)	0.61865 (13)	0.0250 (4)
C23	0.43021 (10)	0.6146 (2)	0.58317 (15)	0.0297 (4)
H23A	0.4362	0.5307	0.6444	0.045*
H23B	0.4718	0.6148	0.5599	0.045*
H23C	0.3908	0.5770	0.5218	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0196 (5)	0.0213 (6)	0.0261 (6)	−0.0029 (4)	0.0049 (5)	−0.0053 (4)
O2	0.0236 (6)	0.0286 (6)	0.0320 (6)	0.0019 (5)	0.0052 (5)	−0.0065 (5)
O3	0.0232 (6)	0.0370 (7)	0.0205 (6)	−0.0089 (5)	−0.0003 (5)	0.0019 (5)
N1	0.0201 (6)	0.0176 (6)	0.0194 (6)	0.0010 (5)	0.0031 (5)	−0.0019 (5)
N2	0.0207 (7)	0.0233 (7)	0.0172 (6)	−0.0032 (5)	0.0034 (5)	0.0002 (5)
C1	0.0230 (8)	0.0166 (7)	0.0250 (8)	−0.0042 (6)	0.0053 (6)	0.0010 (6)
C2	0.0256 (8)	0.0181 (7)	0.0299 (9)	−0.0026 (6)	0.0070 (7)	−0.0002 (6)
C3	0.0249 (9)	0.0220 (8)	0.0385 (10)	0.0004 (7)	0.0049 (7)	0.0034 (7)
C4	0.0288 (9)	0.0246 (8)	0.0322 (9)	−0.0049 (7)	−0.0033 (7)	0.0055 (7)
C5	0.0370 (10)	0.0244 (8)	0.0249 (8)	−0.0061 (7)	0.0031 (7)	−0.0011 (7)
C6	0.0278 (8)	0.0218 (8)	0.0274 (8)	−0.0024 (7)	0.0075 (7)	−0.0015 (6)
C7	0.0239 (8)	0.0154 (7)	0.0251 (8)	−0.0030 (6)	0.0083 (7)	−0.0013 (6)
C8	0.0207 (8)	0.0183 (7)	0.0234 (8)	−0.0002 (6)	0.0046 (6)	−0.0042 (6)
C9	0.0287 (9)	0.0187 (8)	0.0285 (8)	−0.0036 (6)	0.0110 (7)	−0.0005 (6)
C10	0.0334 (9)	0.0211 (8)	0.0218 (8)	0.0001 (7)	0.0084 (7)	0.0016 (6)
C11	0.0254 (8)	0.0219 (8)	0.0186 (7)	0.0004 (6)	0.0043 (6)	−0.0005 (6)
C12	0.0212 (7)	0.0180 (7)	0.0190 (7)	0.0007 (6)	0.0058 (6)	−0.0019 (6)
C13	0.0213 (7)	0.0164 (7)	0.0186 (7)	0.0018 (6)	0.0060 (6)	−0.0021 (6)
C14	0.0199 (7)	0.0230 (8)	0.0177 (7)	0.0004 (6)	0.0043 (6)	−0.0011 (6)
C15	0.0194 (7)	0.0188 (7)	0.0182 (7)	0.0018 (6)	0.0036 (6)	−0.0025 (6)
C16	0.0253 (8)	0.0233 (8)	0.0192 (7)	−0.0009 (6)	0.0012 (6)	0.0012 (6)
C17	0.0241 (8)	0.0292 (9)	0.0190 (7)	−0.0042 (7)	0.0023 (6)	0.0024 (6)
C18	0.0259 (8)	0.0253 (8)	0.0301 (9)	−0.0018 (7)	0.0062 (7)	−0.0002 (7)
C19	0.0323 (9)	0.0246 (9)	0.0317 (9)	−0.0009 (7)	0.0061 (7)	−0.0031 (7)
C20	0.0259 (8)	0.0296 (9)	0.0276 (8)	−0.0036 (7)	0.0018 (7)	0.0009 (7)
C21	0.0258 (8)	0.0282 (9)	0.0227 (8)	−0.0013 (7)	0.0013 (6)	0.0062 (7)
C22	0.0261 (8)	0.0251 (8)	0.0207 (8)	0.0007 (7)	0.0027 (6)	0.0022 (6)
C23	0.0333 (9)	0.0270 (9)	0.0286 (9)	−0.0011 (7)	0.0090 (7)	0.0018 (7)

Geometric parameters (Å, º) top

O1—C7	1.3661 (19)	C10—C11	1.375 (2)
O1—C8	1.3962 (19)	C10—H10	0.9500
O2—C7	1.201 (2)	C11—C12	1.403 (2)
O3—C14	1.219 (2)	C11—H11	0.9500
N1—C15	1.296 (2)	C12—C13	1.401 (2)
N1—C13	1.392 (2)	C12—C14	1.459 (2)
N2—C15	1.3887 (19)	C15—C16	1.493 (2)
N2—C14	1.406 (2)	C16—H16A	0.9800
N2—C17	1.461 (2)	C16—H16B	0.9800
C1—C2	1.389 (2)	C16—H16C	0.9800
C1—C6	1.399 (2)	C17—C22	1.386 (3)
C1—C7	1.487 (2)	C17—C18	1.400 (3)
C2—C3	1.388 (2)	C18—C19	1.387 (3)
C2—H2	0.9500	C18—H18	0.9500
C3—C4	1.387 (3)	C19—C20	1.393 (3)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.390 (3)	C20—C21	1.381 (3)
C4—H4	0.9500	C20—H20	0.9500
C5—C6	1.388 (2)	C21—C22	1.409 (2)
C5—H5	0.9500	C21—H21	0.9500
C6—H6	0.9500	C22—C23	1.486 (2)
C8—C9	1.374 (2)	C23—H23A	0.9800
C8—C13	1.406 (2)	C23—H23B	0.9800
C9—C10	1.401 (2)	C23—H23C	0.9800
C9—H9	0.9500

C7—O1—C8	115.93 (12)	C11—C12—C14	119.88 (14)
C15—N1—C13	117.52 (13)	N1—C13—C12	123.02 (14)
C15—N2—C14	122.18 (14)	N1—C13—C8	119.49 (14)
C15—N2—C17	122.11 (13)	C12—C13—C8	117.48 (14)
C14—N2—C17	115.68 (13)	O3—C14—N2	120.83 (15)
C2—C1—C6	120.09 (15)	O3—C14—C12	124.70 (15)
C2—C1—C7	121.84 (15)	N2—C14—C12	114.47 (13)
C6—C1—C7	118.07 (15)	N1—C15—N2	123.95 (14)
C3—C2—C1	120.16 (16)	N1—C15—C16	119.25 (14)
C3—C2—H2	119.9	N2—C15—C16	116.80 (14)
C1—C2—H2	119.9	C15—C16—H16A	109.5
C4—C3—C2	119.63 (17)	C15—C16—H16B	109.5
C4—C3—H3	120.2	H16A—C16—H16B	109.5
C2—C3—H3	120.2	C15—C16—H16C	109.5
C3—C4—C5	120.66 (16)	H16A—C16—H16C	109.5
C3—C4—H4	119.7	H16B—C16—H16C	109.5
C5—C4—H4	119.7	C22—C17—C18	122.36 (16)
C6—C5—C4	119.82 (17)	C22—C17—N2	119.55 (16)
C6—C5—H5	120.1	C18—C17—N2	117.88 (15)
C4—C5—H5	120.1	C19—C18—C17	119.04 (17)
C5—C6—C1	119.65 (17)	C19—C18—H18	120.5
C5—C6—H6	120.2	C17—C18—H18	120.5
C1—C6—H6	120.2	C18—C19—C20	119.58 (17)
O2—C7—O1	122.72 (15)	C18—C19—H19	120.2
O2—C7—C1	125.87 (15)	C20—C19—H19	120.2
O1—C7—C1	111.41 (13)	C21—C20—C19	120.75 (17)
C9—C8—O1	119.55 (15)	C21—C20—H20	119.6
C9—C8—C13	121.44 (15)	C19—C20—H20	119.6
O1—C8—C13	118.85 (14)	C20—C21—C22	120.87 (17)
C8—C9—C10	119.99 (15)	C20—C21—H21	119.6
C8—C9—H9	120.0	C22—C21—H21	119.6
C10—C9—H9	120.0	C17—C22—C21	117.38 (16)
C11—C10—C9	120.24 (15)	C17—C22—C23	121.95 (16)
C11—C10—H10	119.9	C21—C22—C23	120.66 (16)
C9—C10—H10	119.9	C22—C23—H23A	109.5
C10—C11—C12	119.46 (15)	C22—C23—H23B	109.5
C10—C11—H11	120.3	H23A—C23—H23B	109.5
C12—C11—H11	120.3	C22—C23—H23C	109.5
C13—C12—C11	121.35 (15)	H23A—C23—H23C	109.5
C13—C12—C14	118.73 (14)	H23B—C23—H23C	109.5

C6—C1—C2—C3	−0.5 (2)	O1—C8—C13—C12	174.56 (13)
C7—C1—C2—C3	−179.84 (15)	C15—N2—C14—O3	−179.91 (15)
C1—C2—C3—C4	0.3 (3)	C17—N2—C14—O3	−1.9 (2)
C2—C3—C4—C5	0.1 (3)	C15—N2—C14—C12	−0.8 (2)
C3—C4—C5—C6	−0.3 (3)	C17—N2—C14—C12	177.21 (14)
C4—C5—C6—C1	0.1 (3)	C13—C12—C14—O3	176.86 (16)
C2—C1—C6—C5	0.3 (3)	C11—C12—C14—O3	−1.0 (3)
C7—C1—C6—C5	179.68 (15)	C13—C12—C14—N2	−2.2 (2)
C8—O1—C7—O2	7.2 (2)	C11—C12—C14—N2	179.96 (14)
C8—O1—C7—C1	−172.79 (13)	C13—N1—C15—N2	−0.9 (2)
C2—C1—C7—O2	175.74 (16)	C13—N1—C15—C16	179.36 (14)
C6—C1—C7—O2	−3.6 (3)	C14—N2—C15—N1	2.5 (2)
C2—C1—C7—O1	−4.3 (2)	C17—N2—C15—N1	−175.36 (15)
C6—C1—C7—O1	176.36 (14)	C14—N2—C15—C16	−177.75 (14)
C7—O1—C8—C9	−103.54 (17)	C17—N2—C15—C16	4.4 (2)
C7—O1—C8—C13	81.03 (17)	C15—N2—C17—C22	−92.04 (19)
O1—C8—C9—C10	−176.08 (14)	C14—N2—C17—C22	89.96 (18)
C13—C8—C9—C10	−0.8 (3)	C15—N2—C17—C18	93.06 (19)
C8—C9—C10—C11	1.0 (3)	C14—N2—C17—C18	−84.94 (19)
C9—C10—C11—C12	0.3 (3)	C22—C17—C18—C19	0.4 (3)
C10—C11—C12—C13	−1.9 (2)	N2—C17—C18—C19	175.12 (15)
C10—C11—C12—C14	175.82 (15)	C17—C18—C19—C20	−1.4 (3)
C15—N1—C13—C12	−2.4 (2)	C18—C19—C20—C21	1.5 (3)
C15—N1—C13—C8	177.21 (14)	C19—C20—C21—C22	−0.7 (3)
C11—C12—C13—N1	−178.26 (14)	C18—C17—C22—C21	0.5 (2)
C14—C12—C13—N1	4.0 (2)	N2—C17—C22—C21	−174.21 (14)
C11—C12—C13—C8	2.1 (2)	C18—C17—C22—C23	179.70 (16)
C14—C12—C13—C8	−175.64 (14)	N2—C17—C22—C23	5.0 (2)
C9—C8—C13—N1	179.61 (15)	C20—C21—C22—C17	−0.3 (2)
O1—C8—C13—N1	−5.0 (2)	C20—C21—C22—C23	−179.57 (16)
C9—C8—C13—C12	−0.8 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C17–C22 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1ⁱ	0.95	2.58	3.521 (2)	172
C16—H16c···O2ⁱⁱ	0.98	2.44	3.298 (2)	146
C20—H20···O3ⁱⁱⁱ	0.95	2.59	3.225 (2)	124
C11—H11···Cg1^iv	0.95	2.72	3.5519 (18)	147

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈N₂O₃
M_r	370.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	20.3847 (4), 7.4352 (1), 12.7829 (3)
β (°)	107.489 (2)
V (Å³)	1847.87 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.30 × 0.10 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.470, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7377, 3780, 3432
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.132, 1.05
No. of reflections	3780
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.28

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C17–C22 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1ⁱ	0.95	2.58	3.521 (2)	172
C16—H16c···O2ⁱⁱ	0.98	2.44	3.298 (2)	146
C20—H20···O3ⁱⁱⁱ	0.95	2.59	3.225 (2)	124
C11—H11···Cg1^iv	0.95	2.72	3.5519 (18)	147

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

Footnotes

‡Additional correspondence author, e-mail: adelazaba@yahoo.com.

Acknowledgements

This work was supported by the Research Center of Pharmacy, King Saud University, Riyadh, Saudi Arabia. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

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Volume 68| Part 3| March 2012| Pages o732-o733

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