8-Benz­yloxy-2-methyl-3-(2-methyl­phenyl)quinazolin-4(3H)-one

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

doi:10.1107/S1600536812007362

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o864-o865

doi:10.1107/S1600536812007362

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8-Benzyloxy-2-methyl-3-(2-methylphenyl)quinazolin-4(3H)-one

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 18 February 2012; accepted 18 February 2012; online 29 February 2012)

In the title methaqualone analogue, C₂₃H₂₀N₂O₂, the planes of the terminal aromatic rings [dihedral angle between them = 64.52 (7)°] approximately face the fused-ring methyl group and both are twisted with respect to the pyrimidine plane (r.m.s. deviation = 0.028 Å), forming dihedral angles of 86.9 (3) (with the 2-tolyl ring) and 65.57 (7)°. The 2-tolyl residue is disordered over two almost coplanar but opposite orientations with the major component having a site-occupancy factor of 0.893 (3). The three-dimensional crystal packing is consolidated by C—H⋯O, C—H⋯π and π–π [2-tolyl–2-tolyl centroid–centroid distance = 3.8099 (6) Å] interactions.

Related literature

For recent studies on the synthesis, drug discovery and crystal structures of quinazoline-4(3H)-one derivatives, see: El-Azab et al. (2010 , 2012 ). For the anti-convulsant activity of the title methaqualone analogue, see: El-Azab et al. (2011 ). For a related structure, see: Stephenson et al. (2011 ).

Experimental

Crystal data

C₂₃H₂₀N₂O₂
M_r = 356.41
Monoclinic, P 2₁ /c
a = 18.2611 (3) Å
b = 7.6266 (1) Å
c = 13.2148 (2) Å
β = 91.094 (2)°
V = 1840.09 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.66 mm⁻¹
T = 100 K
0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.967, T_max = 0.998
7568 measured reflections
3775 independent reflections
3559 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.121
S = 1.00
3775 reflections
245 parameters
43 restraints
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1ⁱ	0.95	2.54	3.3250 (15)	140
C17—H17B⋯Cg1ⁱⁱ	0.99	2.62	3.5086 (16)	150
C22—H22⋯Cg1ⁱⁱⁱ	0.95	2.77	3.5692 (16)	143
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+1, -y, -z+1; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536812007362/hb6643sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007362/hb6643Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007362/hb6643Isup3.cml

checkCIF report

Comment top

Quinazoline-4(3H)-one derivatives are known for their various biological activities (El-Azab et al., 2012, 2010). The title methaqualone analogue, 8-benzyloxy-2-methyl-3-(2-methylphenyl)-4(3H)-quinazolinone (I), has been investigated previously for its anti-convulsant activity (El-Azab et al., 2011). Herein, its crystal and molecular structure is described. A related structure with a similar conformation has been reported recently (Stephenson et al., 2011).

In (I), Fig. 1, the 2-tolyl group is orthogonal to the pyrimidine ring [r.m.s. deviation = 0.028 Å] forming a dihedral angle of 87.86 (6)°; the equivalent angle for the minor component of the disordered 2-tolyl ring = 86.9 (3)°. The phenyl ring of the benzyloxy residue is also twisted out of this plane, forming a dihedral angle of 65.57 (7)°. To a first approximation the planes through the terminal rings face towards the methyl group with the dihedral angle between them being 64.52 (7)°.

In the crystal packing, C—H···O and C—H···π interactions, Table 1, combine with π–π [ring centroid(2-tolyl)-to-centroid(2-tolyl)ⁱ distance = 3.8099 (6) Å for symmetry operation i: 2 - x, 2 - y, 1 - z] interactions to consolidate molecules into the three-dimensional architecture, Fig. 2.

Related literature top

For recent studies on the synthesis, drug discovery and crystal structures of quinazoline-4(3H)-one derivatives, see: El-Azab et al. (2010, 2012). For the anti-convulsant activity of the title methaqualone analogue, see: El-Azab et al. (2011). For a related structure, see: Stephenson et al. (2011).

Experimental top

A mixture of 8-hydroxymethaqualone (532 mg, 2 mmol) and benzyl chloride (266 mg, 2.1 mmol) in acetone (15 ml) containing anhydrous potassium carbonate (415 mg, 3 mmol) was heated under reflux for 10 h. The reaction mixture was filtered while hot, the solvent was removed under reduced pressure, and the solid obtained was dried and recrystallized from AcOH as colourless prisms. Yield 86%; M.pt: 449–451 K. ¹H NMR (500 MHz, CDCl₃): δ 7.89 (d, 1H, J = 8.0 Hz), 7.53 (d, 2H, J = 7.0 Hz), 7.41–7.31 (m, 7H), 7.22 (d, 1H, J = 8.0 Hz), 7.17 (d, 1H, J = 7.5 Hz), 5.40 (s, 2H), 2.27 (s, 3H), 2.15 (s, 3H). ¹³C NMR (CDCl₃): δ 17.4, 24.3, 71.3, 117.1, 119.0, 122.1, 126.6, 127.0, 127.6, 127.9, 128.0, 128.6, 129.5, 131.5, 135.3, 136.8, 137.0, 138.8, 153.3, 153.6, 161.5 p.p.m.. MS (70 eV): m/z = 356.

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. The minor disorder component of the toluyl ring is not shown.
	Fig. 2. A view in projection down the b axis of the unit-cell contents of (I). The C—H···O, C—H···π and π–π interactions are shown as orange, bronw and purple dashed lines, respectively.

8-Benzyloxy-2-methyl-3-(2-methylphenyl)quinazolin-4(3H)-one top

Crystal data top

C₂₃H₂₀N₂O₂	F(000) = 752
M_r = 356.41	D_x = 1.287 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 4269 reflections
a = 18.2611 (3) Å	θ = 3.3–76.3°
b = 7.6266 (1) Å	µ = 0.66 mm⁻¹
c = 13.2148 (2) Å	T = 100 K
β = 91.094 (2)°	Prism, colourless
V = 1840.09 (5) Å³	0.35 × 0.30 × 0.25 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3775 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3559 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.015
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.5°, θ_min = 4.8°
ω scan	h = −15→22
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→9
T_min = 0.967, T_max = 0.998	l = −16→15
7568 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0589P)² + 1.3045P] where P = (F_o² + 2F_c²)/3
3775 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.44 e Å⁻³
43 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₃H₂₀N₂O₂	V = 1840.09 (5) Å³
M_r = 356.41	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 18.2611 (3) Å	µ = 0.66 mm⁻¹
b = 7.6266 (1) Å	T = 100 K
c = 13.2148 (2) Å	0.35 × 0.30 × 0.25 mm
β = 91.094 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3775 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3559 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.998	R_int = 0.015
7568 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	43 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.00	Δρ_max = 0.44 e Å⁻³
3775 reflections	Δρ_min = −0.39 e Å⁻³
245 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)
O1	0.90142 (6)	0.63543 (15)	0.61822 (8)	0.0249 (3)
O2	0.61946 (5)	0.31632 (14)	0.48348 (7)	0.0199 (2)
N1	0.84939 (7)	0.63272 (18)	0.45982 (9)	0.0226 (3)
N2	0.73780 (6)	0.48656 (16)	0.42164 (9)	0.0182 (3)
C1	0.85181 (8)	0.58540 (19)	0.56229 (10)	0.0194 (3)
C2	0.79063 (7)	0.47545 (18)	0.59336 (10)	0.0175 (3)
C3	0.78755 (8)	0.41602 (19)	0.69377 (11)	0.0209 (3)
H3	0.8263	0.4407	0.7406	0.025*
C4	0.72731 (8)	0.3212 (2)	0.72336 (11)	0.0230 (3)
H4	0.7248	0.2795	0.7910	0.028*
C5	0.66974 (8)	0.28556 (19)	0.65475 (11)	0.0214 (3)
H5	0.6282	0.2218	0.6766	0.026*
C6	0.67287 (8)	0.34249 (18)	0.55538 (10)	0.0180 (3)
C7	0.73479 (7)	0.43755 (18)	0.52274 (10)	0.0166 (3)
C8	0.79355 (8)	0.5776 (2)	0.39407 (11)	0.0208 (3)
C9	0.80026 (9)	0.6254 (3)	0.28457 (11)	0.0311 (4)
H9A	0.7617	0.5662	0.2449	0.047*
H9B	0.8483	0.5885	0.2605	0.047*
H9C	0.7952	0.7526	0.2767	0.047*
C10	0.90451 (5)	0.75133 (12)	0.42618 (8)	0.0187 (4)	0.893 (3)
C11	0.97023 (6)	0.69096 (11)	0.38786 (9)	0.0231 (4)	0.893 (3)
H11	0.9798	0.5686	0.3852	0.028*	0.893 (3)
C12	1.02189 (5)	0.80957 (15)	0.35339 (9)	0.0275 (4)	0.893 (3)
H12	1.0668	0.7683	0.3272	0.033*	0.893 (3)
C13	1.00783 (5)	0.98854 (14)	0.35724 (9)	0.0288 (4)	0.893 (3)
H13	1.0431	1.0696	0.3337	0.035*	0.893 (3)
C14	0.94210 (6)	1.04890 (10)	0.39556 (9)	0.0263 (4)	0.893 (3)
H14	0.9325	1.1712	0.3982	0.032*	0.893 (3)
C15	0.89044 (5)	0.93030 (14)	0.43003 (8)	0.0210 (4)	0.893 (3)
C16	0.81947 (10)	0.9980 (2)	0.47494 (14)	0.0272 (4)	0.893 (3)
H16A	0.8183	1.1263	0.4706	0.041*	0.893 (3)
H16B	0.8170	0.9621	0.5460	0.041*	0.893 (3)
H16C	0.7776	0.9491	0.4371	0.041*	0.893 (3)
C10'	0.8800 (5)	0.8186 (10)	0.4385 (7)	0.0187 (4)	0.107 (3)
C11'	0.8473 (4)	0.9812 (12)	0.4522 (7)	0.0231 (4)	0.107 (3)
H11'	0.7997	0.9884	0.4796	0.028*	0.107 (3)
C12'	0.8843 (5)	1.1334 (9)	0.4260 (8)	0.0275 (4)	0.107 (3)
H12'	0.8620	1.2445	0.4354	0.033*	0.107 (3)
C13'	0.9540 (5)	1.1229 (10)	0.3860 (8)	0.0288 (4)	0.107 (3)
H13'	0.9793	1.2269	0.3681	0.035*	0.107 (3)
C14'	0.9867 (4)	0.9603 (13)	0.3722 (8)	0.0263 (4)	0.107 (3)
H14'	1.0344	0.9531	0.3449	0.032*	0.107 (3)
C15'	0.9497 (5)	0.8081 (10)	0.3984 (7)	0.0210 (4)	0.107 (3)
C16'	0.9817 (12)	0.638 (3)	0.3910 (16)	0.0272 (4)	0.107 (3)
H16D	1.0309	0.6480	0.3631	0.041*	0.107 (3)
H16E	0.9512	0.5644	0.3465	0.041*	0.107 (3)
H16F	0.9850	0.5846	0.4584	0.041*	0.107 (3)
C17	0.55629 (8)	0.2214 (2)	0.51593 (11)	0.0215 (3)
H17A	0.5314	0.2872	0.5699	0.026*
H17B	0.5712	0.1057	0.5433	0.026*
C18	0.50526 (8)	0.19755 (18)	0.42653 (11)	0.0190 (3)
C19	0.43504 (8)	0.26836 (19)	0.42639 (11)	0.0223 (3)
H19	0.4197	0.3369	0.4822	0.027*
C20	0.38705 (8)	0.2392 (2)	0.34480 (12)	0.0250 (3)
H20	0.3392	0.2882	0.3451	0.030*
C21	0.40895 (8)	0.1388 (2)	0.26318 (11)	0.0238 (3)
H21	0.3762	0.1183	0.2078	0.029*
C22	0.47930 (8)	0.0684 (2)	0.26299 (11)	0.0226 (3)
H22	0.4945	−0.0002	0.2072	0.027*
C23	0.52728 (8)	0.09802 (19)	0.34386 (11)	0.0207 (3)
H23	0.5753	0.0503	0.3430	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0211 (5)	0.0330 (6)	0.0204 (5)	−0.0064 (4)	−0.0038 (4)	−0.0010 (4)
O2	0.0192 (5)	0.0221 (5)	0.0185 (5)	−0.0068 (4)	−0.0001 (4)	0.0020 (4)
N1	0.0210 (6)	0.0291 (7)	0.0176 (6)	−0.0074 (5)	−0.0013 (5)	0.0010 (5)
N2	0.0185 (6)	0.0198 (6)	0.0163 (5)	−0.0020 (5)	0.0004 (4)	−0.0005 (5)
C1	0.0193 (6)	0.0213 (7)	0.0175 (6)	0.0001 (5)	−0.0004 (5)	−0.0013 (5)
C2	0.0184 (6)	0.0159 (6)	0.0183 (6)	0.0019 (5)	0.0006 (5)	−0.0008 (5)
C3	0.0242 (7)	0.0204 (7)	0.0179 (7)	0.0012 (6)	−0.0032 (5)	0.0010 (5)
C4	0.0299 (8)	0.0218 (7)	0.0173 (6)	0.0003 (6)	−0.0002 (6)	0.0047 (6)
C5	0.0242 (7)	0.0182 (7)	0.0218 (7)	−0.0032 (6)	0.0024 (6)	0.0021 (5)
C6	0.0197 (7)	0.0154 (6)	0.0189 (6)	−0.0005 (5)	−0.0008 (5)	−0.0015 (5)
C7	0.0192 (6)	0.0143 (6)	0.0163 (6)	0.0017 (5)	0.0007 (5)	−0.0007 (5)
C8	0.0200 (7)	0.0245 (7)	0.0176 (7)	−0.0044 (6)	−0.0017 (5)	−0.0002 (5)
C9	0.0302 (8)	0.0455 (10)	0.0176 (7)	−0.0165 (7)	−0.0025 (6)	0.0032 (7)
C10	0.0171 (8)	0.0232 (9)	0.0157 (7)	−0.0025 (6)	−0.0008 (6)	−0.0019 (6)
C11	0.0201 (9)	0.0283 (11)	0.0209 (8)	−0.0011 (8)	0.0000 (6)	−0.0036 (8)
C12	0.0183 (8)	0.0437 (11)	0.0204 (8)	−0.0057 (7)	0.0017 (6)	−0.0031 (7)
C13	0.0285 (9)	0.0391 (11)	0.0187 (8)	−0.0159 (8)	−0.0024 (6)	0.0024 (7)
C14	0.0329 (9)	0.0265 (9)	0.0193 (8)	−0.0094 (7)	−0.0059 (6)	0.0014 (7)
C15	0.0209 (8)	0.0254 (8)	0.0165 (7)	−0.0004 (7)	−0.0033 (6)	−0.0012 (6)
C16	0.0284 (9)	0.0250 (9)	0.0284 (9)	0.0046 (7)	0.0010 (7)	−0.0032 (7)
C10'	0.0171 (8)	0.0232 (9)	0.0157 (7)	−0.0025 (6)	−0.0008 (6)	−0.0019 (6)
C11'	0.0201 (9)	0.0283 (11)	0.0209 (8)	−0.0011 (8)	0.0000 (6)	−0.0036 (8)
C12'	0.0183 (8)	0.0437 (11)	0.0204 (8)	−0.0057 (7)	0.0017 (6)	−0.0031 (7)
C13'	0.0285 (9)	0.0391 (11)	0.0187 (8)	−0.0159 (8)	−0.0024 (6)	0.0024 (7)
C14'	0.0329 (9)	0.0265 (9)	0.0193 (8)	−0.0094 (7)	−0.0059 (6)	0.0014 (7)
C15'	0.0209 (8)	0.0254 (8)	0.0165 (7)	−0.0004 (7)	−0.0033 (6)	−0.0012 (6)
C16'	0.0284 (9)	0.0250 (9)	0.0284 (9)	0.0046 (7)	0.0010 (7)	−0.0032 (7)
C17	0.0211 (7)	0.0219 (7)	0.0217 (7)	−0.0072 (6)	0.0028 (5)	0.0011 (6)
C18	0.0204 (7)	0.0160 (6)	0.0206 (7)	−0.0059 (5)	0.0029 (5)	0.0016 (5)
C19	0.0231 (7)	0.0191 (7)	0.0248 (7)	−0.0020 (6)	0.0046 (6)	−0.0029 (6)
C20	0.0205 (7)	0.0238 (7)	0.0307 (8)	0.0007 (6)	0.0007 (6)	0.0001 (6)
C21	0.0251 (7)	0.0231 (7)	0.0231 (7)	−0.0052 (6)	−0.0018 (6)	0.0014 (6)
C22	0.0268 (7)	0.0198 (7)	0.0212 (7)	−0.0037 (6)	0.0048 (6)	−0.0016 (6)
C23	0.0188 (6)	0.0199 (7)	0.0237 (7)	−0.0015 (5)	0.0045 (5)	0.0010 (6)

Geometric parameters (Å, º) top

O1—C1	1.2195 (18)	C15—C16	1.5259 (19)
O2—C6	1.3632 (17)	C16—H16A	0.9800
O2—C17	1.4347 (16)	C16—H16B	0.9800
N1—C8	1.3919 (18)	C16—H16C	0.9800
N1—C1	1.4012 (18)	C10'—C11'	1.3900
N1—C10	1.4304 (14)	C10'—C15'	1.3900
N1—C10'	1.552 (6)	C11'—C12'	1.3900
N2—C8	1.2906 (19)	C11'—H11'	0.9500
N2—C7	1.3893 (17)	C12'—C13'	1.3900
C1—C2	1.4620 (19)	C12'—H12'	0.9500
C2—C7	1.3993 (19)	C13'—C14'	1.3900
C2—C3	1.4043 (19)	C13'—H13'	0.9500
C3—C4	1.379 (2)	C14'—C15'	1.3900
C3—H3	0.9500	C14'—H14'	0.9500
C4—C5	1.402 (2)	C15'—C16'	1.427 (19)
C4—H4	0.9500	C16'—H16D	0.9800
C5—C6	1.385 (2)	C16'—H16E	0.9800
C5—H5	0.9500	C16'—H16F	0.9800
C6—C7	1.4173 (19)	C17—C18	1.502 (2)
C8—C9	1.499 (2)	C17—H17A	0.9900
C9—H9A	0.9800	C17—H17B	0.9900
C9—H9B	0.9800	C18—C19	1.391 (2)
C9—H9C	0.9800	C18—C23	1.396 (2)
C10—C11	1.3900	C19—C20	1.394 (2)
C10—C15	1.3900	C19—H19	0.9500
C11—C12	1.3900	C20—C21	1.388 (2)
C11—H11	0.9500	C20—H20	0.9500
C12—C13	1.3900	C21—C22	1.392 (2)
C12—H12	0.9500	C21—H21	0.9500
C13—C14	1.3900	C22—C23	1.387 (2)
C13—H13	0.9500	C22—H22	0.9500
C14—C15	1.3900	C23—H23	0.9500
C14—H14	0.9500

C6—O2—C17	115.74 (11)	C15—C14—H14	120.0
C8—N1—C1	122.33 (12)	C14—C15—C10	120.0
C8—N1—C10	120.55 (11)	C14—C15—C16	119.61 (10)
C1—N1—C10	116.99 (11)	C10—C15—C16	120.37 (10)
C8—N1—C10'	115.1 (4)	C11'—C10'—C15'	120.0
C1—N1—C10'	114.0 (4)	C11'—C10'—N1	129.3 (6)
C10—N1—C10'	26.8 (3)	C15'—C10'—N1	110.6 (6)
C8—N2—C7	117.53 (12)	C12'—C11'—C10'	120.0
O1—C1—N1	120.96 (13)	C12'—C11'—H11'	120.0
O1—C1—C2	124.90 (13)	C10'—C11'—H11'	120.0
N1—C1—C2	114.14 (12)	C11'—C12'—C13'	120.0
C7—C2—C3	121.45 (13)	C11'—C12'—H12'	120.0
C7—C2—C1	118.83 (12)	C13'—C12'—H12'	120.0
C3—C2—C1	119.67 (13)	C14'—C13'—C12'	120.0
C4—C3—C2	118.92 (13)	C14'—C13'—H13'	120.0
C4—C3—H3	120.5	C12'—C13'—H13'	120.0
C2—C3—H3	120.5	C13'—C14'—C15'	120.0
C3—C4—C5	120.71 (13)	C13'—C14'—H14'	120.0
C3—C4—H4	119.6	C15'—C14'—H14'	120.0
C5—C4—H4	119.6	C14'—C15'—C10'	120.0
C6—C5—C4	120.56 (13)	C14'—C15'—C16'	122.7 (11)
C6—C5—H5	119.7	C10'—C15'—C16'	117.2 (11)
C4—C5—H5	119.7	C15'—C16'—H16D	109.5
O2—C6—C5	124.95 (13)	C15'—C16'—H16E	109.5
O2—C6—C7	115.28 (12)	H16D—C16'—H16E	109.5
C5—C6—C7	119.76 (13)	C15'—C16'—H16F	109.5
N2—C7—C2	122.95 (12)	H16D—C16'—H16F	109.5
N2—C7—C6	118.47 (12)	H16E—C16'—H16F	109.5
C2—C7—C6	118.56 (12)	O2—C17—C18	108.44 (11)
N2—C8—N1	123.95 (13)	O2—C17—H17A	110.0
N2—C8—C9	118.85 (13)	C18—C17—H17A	110.0
N1—C8—C9	117.18 (13)	O2—C17—H17B	110.0
C8—C9—H9A	109.5	C18—C17—H17B	110.0
C8—C9—H9B	109.5	H17A—C17—H17B	108.4
H9A—C9—H9B	109.5	C19—C18—C23	119.29 (14)
C8—C9—H9C	109.5	C19—C18—C17	120.81 (13)
H9A—C9—H9C	109.5	C23—C18—C17	119.86 (13)
H9B—C9—H9C	109.5	C18—C19—C20	120.31 (14)
C11—C10—C15	120.0	C18—C19—H19	119.8
C11—C10—N1	121.43 (9)	C20—C19—H19	119.8
C15—C10—N1	118.55 (9)	C21—C20—C19	120.19 (14)
C10—C11—C12	120.0	C21—C20—H20	119.9
C10—C11—H11	120.0	C19—C20—H20	119.9
C12—C11—H11	120.0	C20—C21—C22	119.59 (14)
C11—C12—C13	120.0	C20—C21—H21	120.2
C11—C12—H12	120.0	C22—C21—H21	120.2
C13—C12—H12	120.0	C23—C22—C21	120.33 (14)
C14—C13—C12	120.0	C23—C22—H22	119.8
C14—C13—H13	120.0	C21—C22—H22	119.8
C12—C13—H13	120.0	C22—C23—C18	120.28 (13)
C13—C14—C15	120.0	C22—C23—H23	119.9
C13—C14—H14	120.0	C18—C23—H23	119.9

C8—N1—C1—O1	179.94 (14)	C10'—N1—C10—C15	0.0 (8)
C10—N1—C1—O1	−4.3 (2)	C15—C10—C11—C12	0.0
C10'—N1—C1—O1	−33.8 (4)	N1—C10—C11—C12	178.35 (11)
C8—N1—C1—C2	−0.5 (2)	C10—C11—C12—C13	0.0
C10—N1—C1—C2	175.30 (11)	C11—C12—C13—C14	0.0
C10'—N1—C1—C2	145.7 (4)	C12—C13—C14—C15	0.0
O1—C1—C2—C7	175.70 (14)	C13—C14—C15—C10	0.0
N1—C1—C2—C7	−3.84 (19)	C13—C14—C15—C16	178.14 (11)
O1—C1—C2—C3	−1.8 (2)	C11—C10—C15—C14	0.0
N1—C1—C2—C3	178.64 (13)	N1—C10—C15—C14	−178.40 (10)
C7—C2—C3—C4	−1.3 (2)	C11—C10—C15—C16	−178.12 (11)
C1—C2—C3—C4	176.19 (13)	N1—C10—C15—C16	3.48 (13)
C2—C3—C4—C5	−0.5 (2)	C8—N1—C10'—C11'	70.9 (7)
C3—C4—C5—C6	1.1 (2)	C1—N1—C10'—C11'	−77.9 (7)
C17—O2—C6—C5	−0.3 (2)	C10—N1—C10'—C11'	179.4 (13)
C17—O2—C6—C7	−179.54 (12)	C8—N1—C10'—C15'	−107.9 (5)
C4—C5—C6—O2	−179.17 (13)	C1—N1—C10'—C15'	103.3 (5)
C4—C5—C6—C7	0.0 (2)	C10—N1—C10'—C15'	0.6 (5)
C8—N2—C7—C2	−3.1 (2)	C15'—C10'—C11'—C12'	0.0
C8—N2—C7—C6	177.94 (13)	N1—C10'—C11'—C12'	−178.7 (9)
C3—C2—C7—N2	−176.63 (13)	C10'—C11'—C12'—C13'	0.0
C1—C2—C7—N2	5.9 (2)	C11'—C12'—C13'—C14'	0.0
C3—C2—C7—C6	2.3 (2)	C12'—C13'—C14'—C15'	0.0
C1—C2—C7—C6	−175.14 (12)	C13'—C14'—C15'—C10'	0.0
O2—C6—C7—N2	−3.42 (19)	C13'—C14'—C15'—C16'	−176.7 (13)
C5—C6—C7—N2	177.33 (13)	C11'—C10'—C15'—C14'	0.0
O2—C6—C7—C2	177.57 (12)	N1—C10'—C15'—C14'	178.9 (7)
C5—C6—C7—C2	−1.7 (2)	C11'—C10'—C15'—C16'	176.9 (13)
C7—N2—C8—N1	−1.7 (2)	N1—C10'—C15'—C16'	−4.2 (12)
C7—N2—C8—C9	177.14 (14)	C6—O2—C17—C18	−177.34 (12)
C1—N1—C8—N2	3.5 (2)	O2—C17—C18—C19	−118.44 (14)
C10—N1—C8—N2	−172.17 (13)	O2—C17—C18—C23	63.87 (17)
C10'—N1—C8—N2	−142.4 (4)	C23—C18—C19—C20	0.4 (2)
C1—N1—C8—C9	−175.34 (14)	C17—C18—C19—C20	−177.28 (13)
C10—N1—C8—C9	9.0 (2)	C18—C19—C20—C21	0.2 (2)
C10'—N1—C8—C9	38.8 (4)	C19—C20—C21—C22	−0.4 (2)
C8—N1—C10—C11	−92.72 (14)	C20—C21—C22—C23	0.1 (2)
C1—N1—C10—C11	91.40 (13)	C21—C22—C23—C18	0.5 (2)
C10'—N1—C10—C11	−178.4 (8)	C19—C18—C23—C22	−0.7 (2)
C8—N1—C10—C15	85.66 (14)	C17—C18—C23—C22	176.98 (13)
C1—N1—C10—C15	−90.23 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1ⁱ	0.95	2.54	3.3250 (15)	140
C17—H17B···Cg1ⁱⁱ	0.99	2.62	3.5086 (16)	150
C22—H22···Cg1ⁱⁱⁱ	0.95	2.77	3.5692 (16)	143

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₀N₂O₂
M_r	356.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	18.2611 (3), 7.6266 (1), 13.2148 (2)
β (°)	91.094 (2)
V (Å³)	1840.09 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.66
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.967, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	7568, 3775, 3559
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.121, 1.00
No. of reflections	3775
No. of parameters	245
No. of restraints	43
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.39

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

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1ⁱ	0.95	2.54	3.3250 (15)	140
C17—H17B···Cg1ⁱⁱ	0.99	2.62	3.5086 (16)	150
C22—H22···Cg1ⁱⁱⁱ	0.95	2.77	3.5692 (16)	143

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y, −z+1; (iii) −x+1, y−1/2, −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. The authors also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (grant No. UM·C/HIR/MOHE/SC/12).

References

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