8-Benz-yloxy-2-methyl-3-(2-methyl-phenyl)quinazolin-4(3H)-one.

In the title methaqua-lone analogue, C(23)H(20)N(2)O(2), 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-tol-yl-2-tolyl centroid-centroid distance = 3.8099 (6) Å] inter-actions.

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 = 356.41

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.121

S = 1.00

3775 reflections

245 parameters

43 restraints

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.39 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812007362/hb6643sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812007362/hb6643Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H20N2O2	F(000) = 752
Mr = 356.41	Dx = 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

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	Rint = 0.015
Detector resolution: 10.4041 pixels mm-1	θmax = 76.5°, θmin = 4.8°
ω scan	h = −15→22
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→9
Tmin = 0.967, Tmax = 0.998	l = −16→15
7568 measured reflections

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(Fo2) + (0.0589P)2 + 1.3045P] where P = (Fo2 + 2Fc2)/3
3775 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.44 e Å−3
43 restraints	Δρmin = −0.39 e Å−3

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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

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) ; (ii) ; (iii) .