1',6-Dimethyl-4'-phenyl-dispiro-[1-benzopyran-3(4H),3'-pyrrolidine-2',3''-indoline]-2,2''-dione.

In the title compound, C(27)H(24)N(2)O(3), the five-membered pyrroldine ring adopts an envelope conformation (with the N atom in the flap position) and the six-membered pyran-one ring of the coumarine ring system adopts a slightly distorted boat conformation. The oxindole unit makes dihedral angles of 89.7 (1) and 25.6 (1)°, respectively, with the pyrrolidine ring and the coumarin ring system. The mol-ecular structure is stabilized by two intra-molecular C-H⋯O contacts and two intra-molecular π-π inter-actions [centroid-centroid seperations of 3.514 (1) and 3.623 (1) Å]. The crystal packing features N-H⋯O hydrogen bonds, which link the mol-ecules into cyclic centrosymmetric R(2) (2)(8) dimers, and C-H⋯π inter-actions.

Related literature

For background to the applications of pyrrolidine derivatives, see: Huryn et al. (1991 ▶) ; Suzuki et al. (1994 ▶); Waldmann (1995 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶) . For closely related pyrrolidine structures, see: Selvanayagam et al. (2011 ▶); Ali et al. (2010 ▶).

Experimental

Crystal data

C27H24N2O3

M = 424.48

Monoclinic,

a = 11.1019 (5) Å

b = 11.1740 (4) Å

c = 17.8156 (7) Å

β = 100.986 (2)°

V = 2169.57 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.22 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.986

20613 measured reflections

4481 independent reflections

3019 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.116

S = 1.02

4481 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia (1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050768/bt5722sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050768/bt5722Isup2.hkl

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

C27H24N2O3	F(000) = 896
Mr = 424.48	Dx = 1.300 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4502 reflections
a = 11.1019 (5) Å	θ = 2.2–26.5°
b = 11.1740 (4) Å	µ = 0.09 mm−1
c = 17.8156 (7) Å	T = 293 K
β = 100.986 (2)°	Block, colourless
V = 2169.57 (15) Å3	0.25 × 0.22 × 0.17 mm
Z = 4

Bruker APEXII CCD diffractometer	4481 independent reflections
Radiation source: fine-focus sealed tube	3019 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 10.0 pixels mm-1	θmax = 26.5°, θmin = 2.2°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→14
Tmin = 0.979, Tmax = 0.986	l = −22→22
20613 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.3552P] where P = (Fo2 + 2Fc2)/3
4481 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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
O2	0.35755 (11)	0.44958 (10)	0.11728 (6)	0.0466 (3)
O1	0.34196 (11)	0.02802 (11)	−0.00536 (7)	0.0528 (3)
N2	0.49556 (12)	0.06511 (12)	0.09708 (8)	0.0435 (3)
H2	0.5521	0.0230	0.0830	0.052*
O3	0.16634 (11)	0.41384 (12)	0.12218 (7)	0.0585 (4)
C12	0.40194 (14)	0.18543 (14)	0.17156 (8)	0.0363 (4)
N1	0.19474 (12)	0.10995 (13)	0.11455 (8)	0.0442 (4)
C2	0.25947 (13)	0.27281 (13)	0.04687 (8)	0.0341 (4)
C14	0.46468 (15)	0.34523 (14)	0.03236 (9)	0.0379 (4)
C6	0.38139 (15)	0.07699 (14)	0.05603 (9)	0.0392 (4)
C19	0.46720 (15)	0.41461 (14)	0.09636 (9)	0.0400 (4)
C13	0.34156 (14)	0.30656 (15)	−0.00996 (8)	0.0380 (4)
H13A	0.3506	0.2382	−0.0420	0.046*
H13B	0.3039	0.3710	−0.0427	0.046*
C15	0.57578 (16)	0.31341 (16)	0.01419 (10)	0.0473 (4)
H15	0.5765	0.2665	−0.0289	0.057*
C20	0.25466 (15)	0.38168 (15)	0.09804 (9)	0.0400 (4)
C7	0.51132 (15)	0.12974 (14)	0.16579 (9)	0.0394 (4)
C1	0.30808 (14)	0.16185 (14)	0.09964 (8)	0.0351 (4)
C3	0.12491 (14)	0.23631 (15)	0.00972 (9)	0.0406 (4)
H3	0.0707	0.2915	0.0303	0.049*
C8	0.61422 (17)	0.13835 (16)	0.22169 (11)	0.0522 (5)
H8	0.6868	0.1002	0.2169	0.063*
C18	0.57418 (17)	0.45345 (15)	0.14141 (10)	0.0490 (5)
H18	0.5730	0.5013	0.1840	0.059*
C26	0.12318 (17)	0.16023 (18)	−0.12513 (10)	0.0553 (5)
H26	0.1662	0.0924	−0.1050	0.066*
C4	0.10654 (15)	0.11394 (16)	0.04305 (10)	0.0483 (4)
H4A	0.0235	0.1054	0.0520	0.058*
H4B	0.1224	0.0508	0.0089	0.058*
C21	0.09077 (15)	0.24589 (16)	−0.07623 (10)	0.0441 (4)
C17	0.68353 (17)	0.41960 (17)	0.12189 (11)	0.0546 (5)
H17	0.7570	0.4445	0.1521	0.065*
C11	0.39406 (17)	0.24889 (15)	0.23647 (9)	0.0467 (4)
H11	0.3203	0.2836	0.2424	0.056*
C16	0.68632 (16)	0.34950 (18)	0.05845 (11)	0.0533 (5)
C10	0.4981 (2)	0.26011 (17)	0.29294 (10)	0.0555 (5)
H10	0.4949	0.3049	0.3365	0.067*
C5	0.20686 (19)	−0.00762 (19)	0.15049 (12)	0.0687 (6)
H5A	0.1292	−0.0317	0.1617	0.103*
H5B	0.2667	−0.0041	0.1971	0.103*
H5C	0.2326	−0.0646	0.1164	0.103*
C9	0.60616 (19)	0.20576 (18)	0.28527 (11)	0.0579 (5)
H9	0.6751	0.2147	0.3237	0.069*
C22	0.02522 (19)	0.3442 (2)	−0.10834 (11)	0.0631 (6)
H22	0.0017	0.4023	−0.0767	0.076*
C25	0.0922 (2)	0.1748 (2)	−0.20316 (12)	0.0705 (6)
H25	0.1149	0.1169	−0.2353	0.085*
C24	0.0285 (3)	0.2734 (3)	−0.23376 (13)	0.0901 (8)
H24	0.0087	0.2833	−0.2865	0.108*
C27	0.8063 (2)	0.3121 (3)	0.03765 (14)	0.0913 (8)
H27A	0.8728	0.3512	0.0709	0.137*
H27B	0.8068	0.3342	−0.0144	0.137*
H27C	0.8156	0.2269	0.0431	0.137*
C23	−0.0059 (3)	0.3576 (3)	−0.18622 (14)	0.0911 (8)
H23	−0.0505	0.4242	−0.2068	0.109*

	U11	U22	U33	U12	U13	U23
O2	0.0484 (7)	0.0371 (7)	0.0556 (7)	0.0021 (5)	0.0129 (6)	−0.0114 (5)
O1	0.0457 (7)	0.0542 (8)	0.0574 (8)	0.0055 (6)	0.0067 (6)	−0.0225 (6)
N2	0.0361 (8)	0.0411 (8)	0.0535 (9)	0.0086 (6)	0.0088 (7)	−0.0062 (6)
O3	0.0518 (8)	0.0640 (9)	0.0642 (8)	0.0145 (6)	0.0222 (7)	−0.0155 (6)
C12	0.0379 (9)	0.0360 (9)	0.0360 (8)	−0.0006 (7)	0.0094 (7)	0.0040 (7)
N1	0.0375 (8)	0.0495 (9)	0.0470 (8)	−0.0073 (6)	0.0118 (7)	0.0046 (6)
C2	0.0307 (8)	0.0364 (9)	0.0371 (8)	0.0033 (6)	0.0108 (7)	−0.0018 (6)
C14	0.0389 (9)	0.0398 (10)	0.0365 (9)	−0.0039 (7)	0.0107 (7)	0.0047 (7)
C6	0.0380 (10)	0.0332 (9)	0.0471 (10)	0.0004 (7)	0.0094 (8)	−0.0031 (7)
C19	0.0432 (10)	0.0341 (9)	0.0438 (9)	−0.0028 (7)	0.0114 (8)	0.0024 (7)
C13	0.0389 (9)	0.0403 (10)	0.0365 (9)	−0.0013 (7)	0.0118 (7)	−0.0004 (7)
C15	0.0434 (11)	0.0599 (12)	0.0419 (10)	−0.0063 (8)	0.0168 (8)	−0.0018 (8)
C20	0.0411 (10)	0.0397 (10)	0.0403 (9)	0.0087 (7)	0.0101 (8)	0.0011 (7)
C7	0.0395 (10)	0.0364 (10)	0.0420 (9)	−0.0004 (7)	0.0072 (8)	0.0040 (7)
C1	0.0320 (9)	0.0364 (9)	0.0388 (9)	0.0004 (6)	0.0117 (7)	−0.0023 (6)
C3	0.0291 (8)	0.0520 (11)	0.0418 (9)	0.0052 (7)	0.0097 (7)	−0.0034 (7)
C8	0.0437 (11)	0.0516 (12)	0.0572 (11)	0.0063 (8)	−0.0008 (9)	0.0053 (9)
C18	0.0540 (12)	0.0439 (11)	0.0476 (10)	−0.0103 (8)	0.0060 (9)	−0.0043 (8)
C26	0.0453 (11)	0.0694 (14)	0.0519 (11)	−0.0038 (9)	0.0112 (9)	−0.0117 (9)
C4	0.0328 (9)	0.0585 (12)	0.0554 (11)	−0.0083 (8)	0.0131 (8)	−0.0018 (9)
C21	0.0294 (9)	0.0575 (11)	0.0452 (10)	−0.0029 (7)	0.0064 (7)	−0.0039 (8)
C17	0.0460 (11)	0.0616 (13)	0.0535 (11)	−0.0148 (9)	0.0027 (9)	0.0042 (9)
C11	0.0548 (11)	0.0484 (11)	0.0388 (9)	0.0031 (8)	0.0141 (8)	0.0022 (8)
C16	0.0381 (11)	0.0692 (13)	0.0539 (11)	−0.0077 (9)	0.0121 (9)	0.0057 (9)
C10	0.0736 (14)	0.0548 (12)	0.0356 (9)	−0.0020 (10)	0.0043 (9)	−0.0012 (8)
C5	0.0677 (14)	0.0634 (14)	0.0742 (14)	−0.0184 (11)	0.0119 (11)	0.0209 (11)
C9	0.0619 (13)	0.0571 (13)	0.0472 (11)	−0.0044 (10)	−0.0088 (9)	0.0042 (9)
C22	0.0575 (13)	0.0755 (15)	0.0546 (12)	0.0130 (10)	0.0065 (10)	0.0044 (10)
C25	0.0631 (14)	0.0997 (19)	0.0506 (12)	−0.0200 (13)	0.0159 (11)	−0.0186 (12)
C24	0.0876 (19)	0.135 (3)	0.0435 (13)	−0.0132 (17)	0.0025 (12)	0.0093 (15)
C27	0.0437 (13)	0.141 (2)	0.0926 (18)	−0.0061 (14)	0.0221 (12)	−0.0130 (17)
C23	0.098 (2)	0.108 (2)	0.0617 (15)	0.0225 (16)	0.0007 (14)	0.0198 (14)

O2—C20	1.360 (2)	C8—H8	0.9300
O2—C19	1.395 (2)	C18—C17	1.378 (3)
O1—C6	1.2265 (19)	C18—H18	0.9300
N2—C6	1.344 (2)	C26—C25	1.377 (3)
N2—C7	1.403 (2)	C26—C21	1.387 (2)
N2—H2	0.8600	C26—H26	0.9300
O3—C20	1.1984 (18)	C4—H4A	0.9700
C12—C11	1.373 (2)	C4—H4B	0.9700
C12—C7	1.386 (2)	C21—C22	1.380 (3)
C12—C1	1.513 (2)	C17—C16	1.380 (3)
N1—C4	1.452 (2)	C17—H17	0.9300
N1—C1	1.4551 (19)	C11—C10	1.386 (3)
N1—C5	1.456 (2)	C11—H11	0.9300
C2—C20	1.527 (2)	C16—C27	1.508 (3)
C2—C13	1.533 (2)	C10—C9	1.374 (3)
C2—C3	1.568 (2)	C10—H10	0.9300
C2—C1	1.587 (2)	C5—H5A	0.9600
C14—C19	1.375 (2)	C5—H5B	0.9600
C14—C15	1.380 (2)	C5—H5C	0.9600
C14—C13	1.494 (2)	C9—H9	0.9300
C6—C1	1.551 (2)	C22—C23	1.373 (3)
C19—C18	1.371 (2)	C22—H22	0.9300
C13—H13A	0.9700	C25—C24	1.366 (4)
C13—H13B	0.9700	C25—H25	0.9300
C15—C16	1.386 (2)	C24—C23	1.368 (4)
C15—H15	0.9300	C24—H24	0.9300
C7—C8	1.368 (2)	C27—H27A	0.9600
C3—C21	1.510 (2)	C27—H27B	0.9600
C3—C4	1.520 (2)	C27—H27C	0.9600
C3—H3	0.9800	C23—H23	0.9300
C8—C9	1.377 (3)
C20—O2—C19	120.69 (12)	C19—C18—C17	118.16 (16)
C6—N2—C7	111.83 (13)	C19—C18—H18	120.9
C6—N2—H2	124.1	C17—C18—H18	120.9
C7—N2—H2	124.1	C25—C26—C21	120.5 (2)
C11—C12—C7	119.45 (15)	C25—C26—H26	119.7
C11—C12—C1	131.22 (15)	C21—C26—H26	119.7
C7—C12—C1	109.32 (13)	N1—C4—C3	104.60 (13)
C4—N1—C1	106.84 (12)	N1—C4—H4A	110.8
C4—N1—C5	113.81 (14)	C3—C4—H4A	110.8
C1—N1—C5	115.41 (14)	N1—C4—H4B	110.8
C20—C2—C13	106.93 (13)	C3—C4—H4B	110.8
C20—C2—C3	108.67 (12)	H4A—C4—H4B	108.9
C13—C2—C3	115.07 (12)	C22—C21—C26	117.93 (17)
C20—C2—C1	108.38 (12)	C22—C21—C3	119.18 (16)
C13—C2—C1	113.93 (12)	C26—C21—C3	122.89 (16)
C3—C2—C1	103.64 (12)	C18—C17—C16	121.39 (17)
C19—C14—C15	117.51 (15)	C18—C17—H17	119.3
C19—C14—C13	116.99 (14)	C16—C17—H17	119.3
C15—C14—C13	125.45 (15)	C12—C11—C10	118.68 (17)
O1—C6—N2	125.50 (15)	C12—C11—H11	120.7
O1—C6—C1	125.95 (14)	C10—C11—H11	120.7
N2—C6—C1	108.56 (13)	C17—C16—C15	118.37 (17)
C18—C19—C14	122.86 (16)	C17—C16—C27	121.15 (18)
C18—C19—O2	117.23 (15)	C15—C16—C27	120.48 (18)
C14—C19—O2	119.91 (15)	C9—C10—C11	120.71 (17)
C14—C13—C2	109.87 (12)	C9—C10—H10	119.6
C14—C13—H13A	109.7	C11—C10—H10	119.6
C2—C13—H13A	109.7	N1—C5—H5A	109.5
C14—C13—H13B	109.7	N1—C5—H5B	109.5
C2—C13—H13B	109.7	H5A—C5—H5B	109.5
H13A—C13—H13B	108.2	N1—C5—H5C	109.5
C14—C15—C16	121.71 (17)	H5A—C5—H5C	109.5
C14—C15—H15	119.1	H5B—C5—H5C	109.5
C16—C15—H15	119.1	C10—C9—C8	121.21 (18)
O3—C20—O2	116.60 (15)	C10—C9—H9	119.4
O3—C20—C2	125.26 (16)	C8—C9—H9	119.4
O2—C20—C2	118.14 (13)	C23—C22—C21	121.1 (2)
C8—C7—C12	122.43 (16)	C23—C22—H22	119.4
C8—C7—N2	128.25 (16)	C21—C22—H22	119.4
C12—C7—N2	109.30 (14)	C24—C25—C26	120.6 (2)
N1—C1—C12	113.26 (12)	C24—C25—H25	119.7
N1—C1—C6	113.72 (13)	C26—C25—H25	119.7
C12—C1—C6	100.85 (12)	C25—C24—C23	119.5 (2)
N1—C1—C2	102.19 (12)	C25—C24—H24	120.3
C12—C1—C2	117.85 (12)	C23—C24—H24	120.3
C6—C1—C2	109.42 (12)	C16—C27—H27A	109.5
C21—C3—C4	115.70 (14)	C16—C27—H27B	109.5
C21—C3—C2	116.39 (13)	H27A—C27—H27B	109.5
C4—C3—C2	104.89 (12)	C16—C27—H27C	109.5
C21—C3—H3	106.4	H27A—C27—H27C	109.5
C4—C3—H3	106.4	H27B—C27—H27C	109.5
C2—C3—H3	106.4	C24—C23—C22	120.3 (2)
C7—C8—C9	117.45 (17)	C24—C23—H23	119.8
C7—C8—H8	121.3	C22—C23—H23	119.8
C9—C8—H8	121.3
C7—N2—C6—O1	−178.23 (16)	N2—C6—C1—C2	121.92 (14)
C7—N2—C6—C1	1.28 (18)	C20—C2—C1—N1	90.74 (14)
C15—C14—C19—C18	0.6 (2)	C13—C2—C1—N1	−150.36 (12)
C13—C14—C19—C18	178.27 (15)	C3—C2—C1—N1	−24.59 (14)
C15—C14—C19—O2	179.87 (14)	C20—C2—C1—C12	−34.08 (17)
C13—C14—C19—O2	−2.5 (2)	C13—C2—C1—C12	84.81 (16)
C20—O2—C19—C18	−153.29 (15)	C3—C2—C1—C12	−149.41 (13)
C20—O2—C19—C14	27.4 (2)	C20—C2—C1—C6	−148.42 (13)
C19—C14—C13—C2	−39.92 (19)	C13—C2—C1—C6	−29.53 (17)
C15—C14—C13—C2	137.50 (16)	C3—C2—C1—C6	96.25 (14)
C20—C2—C13—C14	56.40 (16)	C20—C2—C3—C21	116.31 (15)
C3—C2—C13—C14	177.18 (13)	C13—C2—C3—C21	−3.5 (2)
C1—C2—C13—C14	−63.32 (17)	C1—C2—C3—C21	−128.57 (14)
C19—C14—C15—C16	0.0 (3)	C20—C2—C3—C4	−114.43 (14)
C13—C14—C15—C16	−177.36 (16)	C13—C2—C3—C4	125.75 (14)
C19—O2—C20—O3	175.48 (14)	C1—C2—C3—C4	0.70 (15)
C19—O2—C20—C2	−5.5 (2)	C12—C7—C8—C9	−0.2 (3)
C13—C2—C20—O3	143.17 (17)	N2—C7—C8—C9	−178.56 (17)
C3—C2—C20—O3	18.4 (2)	C14—C19—C18—C17	−1.0 (3)
C1—C2—C20—O3	−93.61 (19)	O2—C19—C18—C17	179.80 (15)
C13—C2—C20—O2	−35.73 (18)	C1—N1—C4—C3	−42.03 (16)
C3—C2—C20—O2	−160.51 (14)	C5—N1—C4—C3	−170.61 (14)
C1—C2—C20—O2	87.49 (16)	C21—C3—C4—N1	153.41 (14)
C11—C12—C7—C8	−2.1 (2)	C2—C3—C4—N1	23.74 (16)
C1—C12—C7—C8	178.14 (15)	C25—C26—C21—C22	1.1 (3)
C11—C12—C7—N2	176.58 (14)	C25—C26—C21—C3	−178.44 (17)
C1—C12—C7—N2	−3.23 (18)	C4—C3—C21—C22	136.12 (17)
C6—N2—C7—C8	179.74 (16)	C2—C3—C21—C22	−100.01 (19)
C6—N2—C7—C12	1.21 (19)	C4—C3—C21—C26	−44.4 (2)
C4—N1—C1—C12	169.27 (13)	C2—C3—C21—C26	79.5 (2)
C5—N1—C1—C12	−63.08 (19)	C19—C18—C17—C16	0.6 (3)
C4—N1—C1—C6	−76.35 (16)	C7—C12—C11—C10	3.1 (2)
C5—N1—C1—C6	51.30 (19)	C1—C12—C11—C10	−177.14 (16)
C4—N1—C1—C2	41.45 (15)	C18—C17—C16—C15	0.0 (3)
C5—N1—C1—C2	169.10 (14)	C18—C17—C16—C27	−179.60 (19)
C11—C12—C1—N1	−54.2 (2)	C14—C15—C16—C17	−0.4 (3)
C7—C12—C1—N1	125.58 (14)	C14—C15—C16—C27	179.28 (18)
C11—C12—C1—C6	−176.09 (17)	C12—C11—C10—C9	−2.0 (3)
C7—C12—C1—C6	3.69 (16)	C11—C10—C9—C8	−0.3 (3)
C11—C12—C1—C2	65.0 (2)	C7—C8—C9—C10	1.4 (3)
C7—C12—C1—C2	−115.27 (15)	C26—C21—C22—C23	−0.7 (3)
O1—C6—C1—N1	55.0 (2)	C3—C21—C22—C23	178.8 (2)
N2—C6—C1—N1	−124.53 (14)	C21—C26—C25—C24	−0.3 (3)
O1—C6—C1—C12	176.54 (16)	C26—C25—C24—C23	−0.8 (4)
N2—C6—C1—C12	−2.97 (16)	C25—C24—C23—C22	1.2 (4)
O1—C6—C1—C2	−58.6 (2)	C21—C22—C23—C24	−0.4 (4)

Cg2 is the centroid of the C7–C12 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3	0.98	2.24	2.795 (2)	115
C4—H4B···O1	0.97	2.51	3.059 (2)	116
C13—H13A···O1	0.97	2.44	3.114 (2)	126
C26—H26···O1	0.93	2.48	3.265 (2)	142
N2—H2···O1i	0.86	2.06	2.852 (2)	153.
C18—H18···Cg2ii	0.93	2.88	3.758 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C7–C12 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1	0.97	2.44	3.114 (2)	126
C26—H26⋯O1	0.93	2.48	3.265 (2)	142
N2—H2⋯O1i	0.86	2.06	2.852 (2)	153
C18—H18⋯Cg2ii	0.93	2.88	3.758 (2)	157

Symmetry codes: (i) ; (ii) .