2'-Methyl-3,5-diphenyl-spiro-[4,6-dioxa-2-aza-bicyclo-[3.2.0]hept-2-ene-7,4'-iso-quinoline]-1',3'(2'H,4'H)-dione.

In the title compound, C(25)H(18)N(2)O(4), the tetra-hydro-pyridine ring adopts a distorted envelope conformation with the spiro C atom at the flap position [deviation = 0.470 (2) Å]. The dihydro-oxazole ring is planar (r.m.s. deviation = 0.013 Å) and it makes dihedral angles of 73.43 (8) and 4.24 (8)° with the two attached phenyl rings. The dihedral angle between oxetane and oxazole planes is 67.44 (9)°. In the crystal structure, C-H⋯O hydrogen bonds link neighbouring mol-ecules into zigzag chains along the b axis and these chains are linked via C-H⋯π inter-actions.

Related literature

For general background to and applications of isoquinolinedione derivatives, see: Hall et al. (1994 ▶); Malamas & Hohman (1994 ▶); Nan et al. (2004 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For related structures, see: Fun et al. (2010 ▶); Wang et al. (2000 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C25H18N2O4

M = 410.41

Monoclinic,

a = 13.3142 (3) Å

b = 8.0366 (2) Å

c = 19.1913 (5) Å

β = 109.882 (1)°

V = 1931.09 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.79 mm−1

T = 100 K

0.27 × 0.26 × 0.25 mm

Data collection

Bruker SMART APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.815, T max = 0.830

32042 measured reflections

3254 independent reflections

3227 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.150

S = 1.35

3254 reflections

353 parameters

All H-atom parameters refined

Δρmax = 0.80 e Å−3

Δρmin = −0.88 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008718/ci5051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008718/ci5051Isup2.hkl

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

C25H18N2O4	F(000) = 856
Mr = 410.41	Dx = 1.412 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 9894 reflections
a = 13.3142 (3) Å	θ = 3.5–64.6°
b = 8.0366 (2) Å	µ = 0.79 mm−1
c = 19.1913 (5) Å	T = 100 K
β = 109.882 (1)°	Block, colourless
V = 1931.09 (8) Å3	0.27 × 0.26 × 0.25 mm
Z = 4

Bruker SMART APEX DUO CCD area-detector diffractometer	3254 independent reflections
Radiation source: fine-focus sealed tube	3227 reflections with I > 2σ(I)
none	Rint = 0.018
φ and ω scans	θmax = 65.0°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.815, Tmax = 0.830	k = −9→8
32042 measured reflections	l = −22→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	All H-atom parameters refined
wR(F2) = 0.150	w = 1/[σ2(Fo2) + (0.0926P)2 + 0.3391P] where P = (Fo2 + 2Fc2)/3
S = 1.35	(Δ/σ)max = 0.001
3254 reflections	Δρmax = 0.80 e Å−3
353 parameters	Δρmin = −0.88 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.052 (3)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.67405 (9)	0.09357 (15)	0.23596 (6)	0.0292 (3)
O2	0.98657 (9)	0.36419 (16)	0.27093 (6)	0.0317 (3)
O3	0.62301 (8)	0.07638 (12)	0.08429 (5)	0.0200 (3)
O4	0.65067 (8)	−0.12787 (13)	0.00309 (5)	0.0197 (3)
N1	0.83241 (10)	0.22292 (16)	0.25592 (7)	0.0219 (3)
N2	0.82562 (9)	−0.07527 (14)	0.06914 (6)	0.0185 (3)
C1	0.73931 (12)	0.14769 (18)	0.21089 (8)	0.0210 (4)
C2	0.90196 (12)	0.31220 (19)	0.22920 (8)	0.0225 (4)
C3	0.86313 (11)	0.34634 (18)	0.14836 (8)	0.0206 (4)
C4	0.91327 (12)	0.4707 (2)	0.12193 (9)	0.0253 (4)
C5	0.87765 (13)	0.5082 (2)	0.04699 (9)	0.0265 (4)
C6	0.79084 (13)	0.42300 (19)	−0.00134 (9)	0.0244 (4)
C7	0.74074 (12)	0.29813 (19)	0.02473 (8)	0.0216 (4)
C8	0.77731 (11)	0.25907 (18)	0.09976 (8)	0.0187 (4)
C9	0.73081 (11)	0.11985 (18)	0.13037 (8)	0.0190 (4)
C10	0.76955 (11)	−0.06240 (18)	0.12152 (8)	0.0182 (4)
C11	0.65008 (12)	−0.09381 (18)	0.07673 (8)	0.0193 (4)
C12	0.75508 (11)	−0.10798 (17)	0.00665 (8)	0.0182 (4)
C13	0.58169 (11)	−0.21713 (18)	0.09854 (8)	0.0194 (4)
C14	0.59034 (13)	−0.3863 (2)	0.08529 (9)	0.0247 (4)
C15	0.53327 (13)	−0.5023 (2)	0.11064 (9)	0.0278 (4)
C16	0.46778 (12)	−0.4499 (2)	0.14951 (9)	0.0263 (4)
C17	0.45793 (12)	−0.2815 (2)	0.16149 (8)	0.0246 (4)
C18	0.51465 (11)	−0.1653 (2)	0.13609 (8)	0.0219 (4)
C19	0.77737 (12)	−0.12908 (17)	−0.06280 (8)	0.0192 (4)
C20	0.88379 (12)	−0.12115 (18)	−0.05944 (9)	0.0215 (4)
C21	0.90942 (13)	−0.13662 (19)	−0.12331 (9)	0.0259 (4)
C22	0.82889 (14)	−0.1618 (2)	−0.19087 (9)	0.0286 (4)
C23	0.72301 (13)	−0.1716 (2)	−0.19467 (9)	0.0284 (4)
C24	0.69684 (12)	−0.15463 (18)	−0.13063 (8)	0.0229 (4)
C25	0.85260 (14)	0.2178 (2)	0.33612 (8)	0.0267 (4)
H4A	0.9730 (17)	0.530 (3)	0.1601 (11)	0.038 (5)*
H5A	0.9128 (16)	0.594 (3)	0.0298 (11)	0.030 (5)*
H6A	0.7619 (14)	0.453 (2)	−0.0564 (10)	0.023 (4)*
H7A	0.6790 (15)	0.241 (2)	−0.0100 (10)	0.027 (4)*
H10A	0.8042 (13)	−0.122 (2)	0.1680 (10)	0.017 (4)*
H14A	0.6366 (16)	−0.421 (3)	0.0580 (11)	0.036 (5)*
H15A	0.5374 (16)	−0.622 (3)	0.0998 (11)	0.036 (5)*
H16A	0.4261 (15)	−0.531 (3)	0.1681 (10)	0.030 (5)*
H17A	0.4124 (15)	−0.243 (2)	0.1881 (10)	0.025 (4)*
H18A	0.5091 (14)	−0.049 (3)	0.1448 (10)	0.025 (4)*
H20A	0.9383 (15)	−0.105 (2)	−0.0121 (10)	0.022 (4)*
H21A	0.9834 (15)	−0.124 (2)	−0.1203 (9)	0.023 (4)*
H22A	0.8479 (17)	−0.174 (3)	−0.2372 (12)	0.042 (6)*
H23A	0.6682 (16)	−0.191 (3)	−0.2414 (11)	0.031 (5)*
H24A	0.6219 (16)	−0.159 (2)	−0.1330 (10)	0.029 (5)*
H25A	0.7977 (15)	0.286 (2)	0.3470 (10)	0.027 (4)*
H25B	0.8482 (14)	0.103 (3)	0.3493 (10)	0.028 (5)*
H25C	0.9243 (16)	0.267 (2)	0.3603 (11)	0.030 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0334 (7)	0.0323 (7)	0.0290 (6)	−0.0065 (5)	0.0198 (5)	−0.0034 (5)
O2	0.0214 (6)	0.0460 (8)	0.0256 (6)	−0.0050 (5)	0.0051 (5)	−0.0069 (5)
O3	0.0174 (6)	0.0182 (6)	0.0238 (6)	−0.0004 (4)	0.0060 (4)	−0.0003 (4)
O4	0.0182 (6)	0.0235 (6)	0.0182 (5)	−0.0023 (4)	0.0074 (4)	−0.0009 (4)
N1	0.0231 (7)	0.0252 (7)	0.0186 (6)	0.0023 (5)	0.0085 (5)	−0.0009 (5)
N2	0.0191 (6)	0.0170 (6)	0.0201 (6)	0.0012 (4)	0.0076 (5)	0.0001 (5)
C1	0.0239 (8)	0.0185 (8)	0.0226 (8)	0.0023 (6)	0.0107 (6)	0.0005 (6)
C2	0.0205 (8)	0.0240 (8)	0.0237 (8)	0.0023 (6)	0.0085 (6)	−0.0035 (6)
C3	0.0201 (7)	0.0204 (8)	0.0232 (8)	0.0018 (6)	0.0099 (6)	−0.0028 (6)
C4	0.0229 (8)	0.0223 (8)	0.0323 (9)	−0.0032 (6)	0.0117 (7)	−0.0030 (6)
C5	0.0290 (8)	0.0207 (8)	0.0346 (9)	0.0006 (6)	0.0172 (7)	0.0047 (6)
C6	0.0285 (8)	0.0227 (8)	0.0255 (8)	0.0051 (6)	0.0138 (7)	0.0038 (6)
C7	0.0225 (8)	0.0209 (8)	0.0226 (8)	0.0016 (6)	0.0092 (6)	−0.0012 (6)
C8	0.0185 (7)	0.0172 (7)	0.0219 (7)	0.0021 (5)	0.0090 (6)	−0.0008 (5)
C9	0.0178 (7)	0.0192 (7)	0.0209 (7)	0.0002 (5)	0.0077 (6)	−0.0009 (5)
C10	0.0191 (7)	0.0181 (7)	0.0182 (7)	−0.0002 (5)	0.0073 (6)	0.0006 (5)
C11	0.0207 (8)	0.0192 (7)	0.0184 (7)	0.0012 (6)	0.0074 (6)	0.0003 (5)
C12	0.0179 (7)	0.0145 (7)	0.0228 (8)	0.0002 (5)	0.0076 (6)	0.0011 (5)
C13	0.0165 (7)	0.0216 (8)	0.0188 (7)	−0.0017 (6)	0.0045 (6)	0.0008 (6)
C14	0.0260 (8)	0.0246 (8)	0.0265 (8)	−0.0016 (6)	0.0130 (7)	−0.0026 (6)
C15	0.0311 (9)	0.0211 (8)	0.0321 (9)	−0.0044 (6)	0.0116 (7)	−0.0007 (6)
C16	0.0237 (8)	0.0283 (9)	0.0270 (8)	−0.0067 (6)	0.0085 (6)	0.0033 (6)
C17	0.0187 (7)	0.0312 (9)	0.0253 (8)	−0.0020 (6)	0.0095 (6)	0.0011 (6)
C18	0.0188 (7)	0.0226 (8)	0.0242 (8)	0.0005 (6)	0.0071 (6)	0.0006 (6)
C19	0.0231 (8)	0.0137 (7)	0.0217 (8)	−0.0001 (5)	0.0089 (6)	0.0002 (5)
C20	0.0222 (8)	0.0196 (8)	0.0229 (8)	−0.0010 (6)	0.0078 (6)	0.0002 (6)
C21	0.0269 (9)	0.0239 (8)	0.0316 (9)	−0.0013 (6)	0.0158 (7)	−0.0024 (6)
C22	0.0371 (9)	0.0284 (9)	0.0253 (8)	−0.0032 (7)	0.0172 (7)	−0.0053 (6)
C23	0.0310 (9)	0.0319 (9)	0.0213 (8)	−0.0032 (7)	0.0074 (7)	−0.0059 (6)
C24	0.0226 (8)	0.0216 (8)	0.0246 (8)	−0.0006 (6)	0.0081 (6)	−0.0018 (6)
C25	0.0304 (9)	0.0319 (10)	0.0190 (8)	0.0065 (7)	0.0100 (7)	−0.0008 (6)

O1—C1	1.2083 (18)	C11—C13	1.499 (2)
O2—C2	1.2130 (19)	C12—C19	1.470 (2)
O3—C11	1.4343 (17)	C13—C18	1.388 (2)
O3—C9	1.4495 (17)	C13—C14	1.395 (2)
O4—C12	1.3777 (17)	C14—C15	1.391 (2)
O4—C11	1.4421 (16)	C14—H14A	0.98 (2)
N1—C1	1.386 (2)	C15—C16	1.392 (2)
N1—C2	1.399 (2)	C15—H15A	0.99 (2)
N1—C25	1.4702 (18)	C16—C17	1.386 (2)
N2—C12	1.2741 (19)	C16—H16A	1.00 (2)
N2—C10	1.4453 (18)	C17—C18	1.389 (2)
C1—C9	1.5269 (19)	C17—H17A	0.966 (18)
C2—C3	1.485 (2)	C18—H18A	0.96 (2)
C3—C4	1.390 (2)	C19—C24	1.392 (2)
C3—C8	1.394 (2)	C19—C20	1.398 (2)
C4—C5	1.386 (2)	C20—C21	1.385 (2)
C4—H4A	1.00 (2)	C20—H20A	0.960 (19)
C5—C6	1.391 (2)	C21—C22	1.388 (2)
C5—H5A	0.95 (2)	C21—H21A	0.972 (19)
C6—C7	1.389 (2)	C22—C23	1.389 (2)
C6—H6A	1.021 (18)	C22—H22A	1.01 (2)
C7—C8	1.390 (2)	C23—C24	1.393 (2)
C7—H7A	0.979 (19)	C23—H23A	0.96 (2)
C8—C9	1.4925 (19)	C24—H24A	0.98 (2)
C9—C10	1.5810 (19)	C25—H25A	0.99 (2)
C10—C11	1.550 (2)	C25—H25B	0.97 (2)
C10—H10A	0.979 (17)	C25—H25C	0.99 (2)
C11—O3—C9	93.49 (10)	C13—C11—C10	124.00 (12)
C12—O4—C11	105.73 (10)	N2—C12—O4	118.61 (12)
C1—N1—C2	123.94 (12)	N2—C12—C19	124.45 (13)
C1—N1—C25	116.55 (12)	O4—C12—C19	116.93 (12)
C2—N1—C25	119.32 (12)	C18—C13—C14	119.65 (14)
C12—N2—C10	106.25 (12)	C18—C13—C11	120.36 (13)
O1—C1—N1	121.37 (14)	C14—C13—C11	119.86 (13)
O1—C1—C9	122.31 (14)	C15—C14—C13	120.04 (14)
N1—C1—C9	115.96 (12)	C15—C14—H14A	120.9 (12)
O2—C2—N1	121.09 (14)	C13—C14—H14A	119.0 (12)
O2—C2—C3	122.78 (14)	C14—C15—C16	120.06 (15)
N1—C2—C3	116.04 (13)	C14—C15—H15A	120.1 (12)
C4—C3—C8	120.25 (14)	C16—C15—H15A	119.8 (12)
C4—C3—C2	118.33 (14)	C17—C16—C15	119.76 (14)
C8—C3—C2	121.42 (13)	C17—C16—H16A	119.0 (11)
C5—C4—C3	119.85 (14)	C15—C16—H16A	121.2 (11)
C5—C4—H4A	124.3 (12)	C16—C17—C18	120.30 (14)
C3—C4—H4A	115.8 (12)	C16—C17—H17A	120.8 (11)
C4—C5—C6	119.90 (14)	C18—C17—H17A	118.9 (11)
C4—C5—H5A	118.7 (12)	C13—C18—C17	120.17 (14)
C6—C5—H5A	121.4 (12)	C13—C18—H18A	119.1 (11)
C7—C6—C5	120.48 (14)	C17—C18—H18A	120.8 (11)
C7—C6—H6A	118.8 (10)	C24—C19—C20	119.76 (14)
C5—C6—H6A	120.7 (10)	C24—C19—C12	122.41 (13)
C6—C7—C8	119.63 (14)	C20—C19—C12	117.82 (13)
C6—C7—H7A	119.3 (11)	C21—C20—C19	120.39 (15)
C8—C7—H7A	121.1 (11)	C21—C20—H20A	121.0 (11)
C7—C8—C3	119.88 (13)	C19—C20—H20A	118.6 (11)
C7—C8—C9	122.08 (13)	C20—C21—C22	119.69 (15)
C3—C8—C9	117.98 (13)	C20—C21—H21A	119.2 (10)
O3—C9—C8	113.43 (11)	C22—C21—H21A	121.0 (10)
O3—C9—C1	111.72 (11)	C21—C22—C23	120.34 (15)
C8—C9—C1	112.99 (12)	C21—C22—H22A	119.5 (12)
O3—C9—C10	90.15 (10)	C23—C22—H22A	120.2 (12)
C8—C9—C10	117.26 (11)	C22—C23—C24	120.14 (15)
C1—C9—C10	109.26 (11)	C22—C23—H23A	119.7 (11)
N2—C10—C11	106.14 (11)	C24—C23—H23A	120.2 (11)
N2—C10—C9	113.93 (11)	C19—C24—C23	119.68 (14)
C11—C10—C9	84.25 (10)	C19—C24—H24A	119.7 (11)
N2—C10—H10A	113.8 (10)	C23—C24—H24A	120.6 (11)
C11—C10—H10A	120.1 (10)	N1—C25—H25A	108.7 (11)
C9—C10—H10A	115.3 (10)	N1—C25—H25B	107.2 (11)
O3—C11—O4	111.43 (11)	H25A—C25—H25B	110.9 (15)
O3—C11—C13	113.89 (12)	N1—C25—H25C	106.5 (11)
O4—C11—C13	110.76 (11)	H25A—C25—H25C	110.3 (15)
O3—C11—C10	91.97 (10)	H25B—C25—H25C	113.0 (16)
O4—C11—C10	103.17 (11)
C2—N1—C1—O1	−168.82 (14)	C8—C9—C10—C11	−119.42 (13)
C25—N1—C1—O1	6.1 (2)	C1—C9—C10—C11	110.37 (12)
C2—N1—C1—C9	18.0 (2)	C9—O3—C11—O4	−108.01 (12)
C25—N1—C1—C9	−167.07 (13)	C9—O3—C11—C13	125.81 (12)
C1—N1—C2—O2	−174.06 (14)	C9—O3—C11—C10	−3.03 (10)
C25—N1—C2—O2	11.1 (2)	C12—O4—C11—O3	94.44 (12)
C1—N1—C2—C3	9.2 (2)	C12—O4—C11—C13	−137.68 (12)
C25—N1—C2—C3	−165.64 (13)	C12—O4—C11—C10	−3.02 (14)
O2—C2—C3—C4	−14.3 (2)	N2—C10—C11—O3	−110.49 (11)
N1—C2—C3—C4	162.41 (13)	C9—C10—C11—O3	2.79 (9)
O2—C2—C3—C8	166.92 (14)	N2—C10—C11—O4	2.06 (14)
N1—C2—C3—C8	−16.4 (2)	C9—C10—C11—O4	115.34 (11)
C8—C3—C4—C5	0.1 (2)	N2—C10—C11—C13	128.72 (14)
C2—C3—C4—C5	−178.67 (13)	C9—C10—C11—C13	−118.01 (14)
C3—C4—C5—C6	1.0 (2)	C10—N2—C12—O4	−2.00 (16)
C4—C5—C6—C7	−1.3 (2)	C10—N2—C12—C19	179.06 (13)
C5—C6—C7—C8	0.5 (2)	C11—O4—C12—N2	3.43 (17)
C6—C7—C8—C3	0.6 (2)	C11—O4—C12—C19	−177.55 (11)
C6—C7—C8—C9	−176.45 (13)	O3—C11—C13—C18	−12.07 (19)
C4—C3—C8—C7	−0.9 (2)	O4—C11—C13—C18	−138.61 (13)
C2—C3—C8—C7	177.82 (13)	C10—C11—C13—C18	98.05 (17)
C4—C3—C8—C9	176.28 (13)	O3—C11—C13—C14	172.03 (13)
C2—C3—C8—C9	−5.0 (2)	O4—C11—C13—C14	45.49 (17)
C11—O3—C9—C8	122.99 (12)	C10—C11—C13—C14	−77.85 (19)
C11—O3—C9—C1	−107.89 (12)	C18—C13—C14—C15	−1.0 (2)
C11—O3—C9—C10	2.97 (10)	C11—C13—C14—C15	174.94 (13)
C7—C8—C9—O3	−23.27 (19)	C13—C14—C15—C16	−0.3 (2)
C3—C8—C9—O3	159.58 (12)	C14—C15—C16—C17	1.4 (2)
C7—C8—C9—C1	−151.74 (13)	C15—C16—C17—C18	−1.2 (2)
C3—C8—C9—C1	31.12 (17)	C14—C13—C18—C17	1.1 (2)
C7—C8—C9—C10	79.82 (17)	C11—C13—C18—C17	−174.77 (12)
C3—C8—C9—C10	−97.33 (15)	C16—C17—C18—C13	0.0 (2)
O1—C1—C9—O3	19.88 (19)	N2—C12—C19—C24	−175.95 (14)
N1—C1—C9—O3	−166.99 (12)	O4—C12—C19—C24	5.1 (2)
O1—C1—C9—C8	149.23 (14)	N2—C12—C19—C20	3.4 (2)
N1—C1—C9—C8	−37.65 (17)	O4—C12—C19—C20	−175.55 (12)
O1—C1—C9—C10	−78.29 (17)	C24—C19—C20—C21	0.8 (2)
N1—C1—C9—C10	94.83 (14)	C12—C19—C20—C21	−178.63 (13)
C12—N2—C10—C11	−0.22 (14)	C19—C20—C21—C22	−0.7 (2)
C12—N2—C10—C9	−91.04 (14)	C20—C21—C22—C23	0.0 (2)
O3—C9—C10—N2	102.37 (12)	C21—C22—C23—C24	0.6 (2)
C8—C9—C10—N2	−14.29 (18)	C20—C19—C24—C23	−0.2 (2)
C1—C9—C10—N2	−144.50 (12)	C12—C19—C24—C23	179.18 (14)
O3—C9—C10—C11	−2.76 (9)	C22—C23—C24—C19	−0.5 (2)

Cg1 is the centroid of the C13–C18 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O1i	0.97 (2)	2.51 (2)	3.213 (2)	129 (1)
C23—H23A···Cg1ii	0.96 (2)	2.66 (2)	3.5904 (18)	166 (2)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O1i	0.97 (2)	2.51 (2)	3.213 (2)	129 (1)
C23—H23A⋯Cg1ii	0.96 (2)	2.66 (2)	3.5904 (18)	166 (2)

Symmetry codes: (i) ; (ii) .