4'-(4-Methoxy-phen-yl)-1,1',1''-trimethyl-dispiro-[indoline-3,2'-pyrrolidine-3',3''-pyrrolidine]-2,2'',5''-trione.

In the title compound, C(24)H(25)N(3)O(4), the pyrrolidine ring adopts an envelope conformation while the pyrrolidine-2'',5''-dione ring adopts a twist conformation. The indoline unit is planar [maximum deviation of -0.050 (9) Å] and forms a dihedral angle of 40.36 (4)° with the methoxy-phenyl ring. Intra-molecular C-H⋯O hydrogen bonds are observed. In the crystal, mol-ecules are linked into a two-dimensional network parallel to the ab plane by inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Related literature

For the biological activity of spiro-pyrrolidine-containing compounds, see: Araki et al. (2002 ▶); Gore et al. (1991 ▶); James et al. (1991 ▶); Kobayashi et al. (1991 ▶); Tietze et al. (1988 ▶). For the biological activity of indole derivatives, see: Harris & Uhle (1960 ▶); Ho et al. (1986 ▶); Stevenson et al. (2000 ▶). For a related structure, see: Govind et al. (2003 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C24H25N3O4

M = 419.47

Orthorhombic,

a = 11.2074 (3) Å

b = 11.2406 (3) Å

c = 33.6082 (9) Å

V = 4233.9 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.17 × 0.15 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.978, T max = 0.987

17736 measured reflections

5023 independent reflections

3269 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.152

S = 1.07

5023 reflections

284 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021114/ci2815sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021114/ci2815Isup2.hkl

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

C24H25N3O4	F(000) = 1776
Mr = 419.47	Dx = 1.316 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5049 reflections
a = 11.2074 (3) Å	θ = 2.4–25.7°
b = 11.2406 (3) Å	µ = 0.09 mm−1
c = 33.6082 (9) Å	T = 293 K
V = 4233.9 (2) Å3	Prism, colourless
Z = 8	0.25 × 0.17 × 0.15 mm

Bruker Kappa APEXII area-detector diffractometer	5023 independent reflections
Radiation source: fine-focus sealed tube	3269 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω and φ scans	θmax = 28.4°, θmin = 1.2°
Absorption correction: multi-scan (Blessing, 1995)	h = −14→11
Tmin = 0.978, Tmax = 0.987	k = −15→11
17736 measured reflections	l = −43→43

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) = 0.152	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0744P)2 + 0.5831P] where P = (Fo2 + 2Fc2)/3
5023 reflections	(Δ/σ)max = 0.001
284 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.18 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
C1	0.01846 (15)	0.47299 (15)	0.12817 (5)	0.0327 (4)
C2	−0.06510 (14)	0.36884 (14)	0.11357 (5)	0.0316 (4)
C3	−0.09503 (15)	0.40199 (16)	0.06949 (5)	0.0365 (4)
H3	−0.0535	0.3440	0.0527	0.044*
C4	−0.03321 (17)	0.52114 (18)	0.06291 (5)	0.0433 (5)
H4A	−0.0046	0.5282	0.0358	0.052*
H4B	−0.0868	0.5868	0.0685	0.052*
C5	−0.05564 (15)	0.56643 (16)	0.15170 (5)	0.0357 (4)
C6	0.08728 (16)	0.49862 (17)	0.19406 (6)	0.0408 (4)
C7	0.1549 (2)	0.4819 (2)	0.22787 (7)	0.0582 (6)
H7	0.1375	0.5215	0.2515	0.070*
C8	0.2500 (2)	0.4037 (2)	0.22515 (7)	0.0665 (7)
H8	0.2959	0.3885	0.2476	0.080*
C9	0.2780 (2)	0.3480 (2)	0.18998 (7)	0.0608 (6)
H9	0.3434	0.2972	0.1888	0.073*
C10	0.20970 (17)	0.36673 (17)	0.15631 (6)	0.0456 (5)
H10	0.2295	0.3301	0.1324	0.055*
C11	0.11189 (15)	0.44049 (15)	0.15873 (5)	0.0353 (4)
C12	−0.16608 (15)	0.33962 (16)	0.14310 (5)	0.0371 (4)
H12A	−0.1860	0.4087	0.1591	0.045*
H12B	−0.2371	0.3133	0.1291	0.045*
C13	−0.11700 (16)	0.24208 (18)	0.16851 (6)	0.0425 (4)
C14	0.00594 (15)	0.25280 (16)	0.11418 (5)	0.0350 (4)
C15	−0.22493 (16)	0.39732 (16)	0.05782 (5)	0.0364 (4)
C16	−0.26396 (17)	0.30838 (16)	0.03233 (5)	0.0402 (4)
H16	−0.2092	0.2538	0.0224	0.048*
C17	−0.38205 (17)	0.29936 (17)	0.02148 (6)	0.0443 (5)
H17	−0.4061	0.2395	0.0041	0.053*
C18	−0.46497 (16)	0.37864 (17)	0.03623 (5)	0.0385 (4)
C19	−0.42807 (17)	0.46898 (18)	0.06074 (6)	0.0455 (5)
H19	−0.4829	0.5242	0.0702	0.055*
C20	−0.30887 (17)	0.47782 (18)	0.07131 (6)	0.0467 (5)
H20	−0.2848	0.5395	0.0879	0.056*
C21	−0.67018 (18)	0.4326 (2)	0.04175 (7)	0.0595 (6)
H21A	−0.6672	0.4262	0.0702	0.089*
H21B	−0.7469	0.4068	0.0324	0.089*
H21C	−0.6575	0.5139	0.0341	0.089*
C22	−0.0594 (2)	0.6521 (2)	0.21968 (7)	0.0586 (6)
H22A	−0.1135	0.7077	0.2077	0.088*
H22B	0.0048	0.6945	0.2322	0.088*
H22C	−0.1011	0.6058	0.2393	0.088*
C23	0.0372 (2)	0.0838 (2)	0.16109 (7)	0.0633 (6)
H23A	0.0928	0.1050	0.1816	0.095*
H23B	0.0795	0.0491	0.1391	0.095*
H23C	−0.0193	0.0274	0.1713	0.095*
C24	0.12923 (19)	0.63178 (18)	0.09418 (7)	0.0540 (5)
H24A	0.0752	0.6924	0.1031	0.081*
H24B	0.1609	0.6532	0.0686	0.081*
H24C	0.1934	0.6240	0.1129	0.081*
N1	−0.01162 (14)	0.57366 (14)	0.18924 (4)	0.0424 (4)
N2	0.06588 (13)	0.51895 (13)	0.09103 (4)	0.0381 (4)
N3	−0.02527 (14)	0.18934 (13)	0.14773 (5)	0.0416 (4)
O1	−0.13847 (12)	0.62471 (12)	0.13906 (4)	0.0506 (4)
O2	0.07934 (11)	0.21993 (11)	0.09054 (4)	0.0455 (3)
O3	−0.14963 (13)	0.21122 (15)	0.20112 (4)	0.0626 (4)
O4	−0.58015 (12)	0.36018 (13)	0.02477 (4)	0.0529 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0316 (9)	0.0305 (9)	0.0360 (9)	0.0035 (7)	−0.0024 (7)	−0.0031 (7)
C2	0.0300 (8)	0.0310 (8)	0.0337 (9)	0.0008 (7)	0.0001 (7)	−0.0048 (7)
C3	0.0377 (9)	0.0411 (10)	0.0308 (9)	0.0030 (8)	−0.0017 (7)	−0.0047 (8)
C4	0.0462 (11)	0.0472 (11)	0.0365 (10)	−0.0004 (9)	−0.0011 (8)	0.0048 (9)
C5	0.0345 (9)	0.0329 (9)	0.0397 (10)	0.0020 (8)	−0.0012 (8)	−0.0045 (8)
C6	0.0390 (10)	0.0426 (10)	0.0409 (11)	−0.0025 (8)	−0.0057 (8)	−0.0017 (8)
C7	0.0603 (13)	0.0691 (15)	0.0453 (12)	−0.0024 (12)	−0.0145 (10)	−0.0015 (11)
C8	0.0634 (14)	0.0700 (16)	0.0662 (16)	0.0002 (13)	−0.0310 (13)	0.0131 (13)
C9	0.0487 (12)	0.0501 (12)	0.0835 (17)	0.0085 (10)	−0.0224 (12)	0.0048 (12)
C10	0.0367 (10)	0.0390 (10)	0.0611 (12)	0.0032 (8)	−0.0081 (9)	−0.0028 (9)
C11	0.0318 (9)	0.0318 (9)	0.0423 (10)	−0.0023 (7)	−0.0050 (8)	−0.0006 (8)
C12	0.0317 (9)	0.0398 (10)	0.0400 (10)	−0.0002 (8)	0.0002 (8)	−0.0027 (8)
C13	0.0392 (10)	0.0468 (11)	0.0416 (11)	−0.0076 (9)	−0.0038 (9)	0.0011 (9)
C14	0.0350 (9)	0.0315 (9)	0.0385 (10)	−0.0002 (7)	−0.0022 (8)	−0.0044 (8)
C15	0.0407 (10)	0.0363 (9)	0.0323 (9)	0.0044 (8)	−0.0059 (8)	−0.0029 (8)
C16	0.0436 (10)	0.0376 (10)	0.0394 (10)	0.0054 (8)	−0.0029 (8)	−0.0079 (8)
C17	0.0499 (11)	0.0392 (10)	0.0438 (11)	−0.0027 (9)	−0.0081 (9)	−0.0104 (9)
C18	0.0379 (10)	0.0417 (10)	0.0360 (10)	−0.0021 (8)	−0.0071 (8)	0.0024 (8)
C19	0.0438 (11)	0.0444 (11)	0.0482 (11)	0.0102 (9)	−0.0038 (9)	−0.0114 (9)
C20	0.0457 (11)	0.0451 (11)	0.0492 (11)	0.0061 (9)	−0.0118 (9)	−0.0176 (9)
C21	0.0392 (11)	0.0701 (15)	0.0692 (15)	0.0060 (11)	−0.0010 (10)	−0.0035 (12)
C22	0.0547 (13)	0.0710 (15)	0.0501 (13)	0.0037 (11)	0.0039 (10)	−0.0247 (11)
C23	0.0818 (16)	0.0473 (13)	0.0608 (14)	0.0158 (12)	−0.0029 (12)	0.0122 (11)
C24	0.0500 (12)	0.0444 (12)	0.0675 (14)	−0.0118 (9)	0.0000 (11)	0.0069 (10)
N1	0.0433 (9)	0.0453 (9)	0.0387 (9)	0.0044 (7)	−0.0038 (7)	−0.0107 (7)
N2	0.0369 (8)	0.0362 (8)	0.0411 (9)	−0.0048 (7)	0.0012 (7)	0.0017 (7)
N3	0.0475 (9)	0.0348 (8)	0.0427 (9)	0.0038 (7)	−0.0018 (7)	0.0043 (7)
O1	0.0501 (8)	0.0470 (8)	0.0548 (8)	0.0192 (6)	−0.0080 (7)	−0.0098 (7)
O2	0.0473 (7)	0.0394 (7)	0.0498 (8)	0.0078 (6)	0.0059 (6)	−0.0087 (6)
O3	0.0606 (9)	0.0849 (12)	0.0423 (8)	−0.0018 (8)	0.0053 (7)	0.0165 (8)
O4	0.0391 (8)	0.0582 (9)	0.0615 (9)	0.0001 (6)	−0.0094 (7)	−0.0099 (7)

C1—N2	1.452 (2)	C13—N3	1.377 (2)
C1—C11	1.511 (2)	C14—O2	1.202 (2)
C1—C5	1.555 (2)	C14—N3	1.379 (2)
C1—C2	1.577 (2)	C15—C20	1.382 (2)
C2—C14	1.528 (2)	C15—C16	1.387 (2)
C2—C12	1.541 (2)	C16—C17	1.377 (3)
C2—C3	1.564 (2)	C16—H16	0.93
C3—C15	1.509 (2)	C17—C18	1.380 (3)
C3—C4	1.524 (3)	C17—H17	0.93
C3—H3	0.98	C18—O4	1.363 (2)
C4—N2	1.458 (2)	C18—C19	1.371 (3)
C4—H4A	0.97	C19—C20	1.386 (3)
C4—H4B	0.97	C19—H19	0.93
C5—O1	1.213 (2)	C20—H20	0.93
C5—N1	1.357 (2)	C21—O4	1.417 (2)
C6—C7	1.379 (3)	C21—H21A	0.96
C6—C11	1.383 (3)	C21—H21B	0.96
C6—N1	1.402 (2)	C21—H21C	0.96
C7—C8	1.384 (3)	C22—N1	1.453 (2)
C7—H7	0.93	C22—H22A	0.96
C8—C9	1.374 (3)	C22—H22B	0.96
C8—H8	0.93	C22—H22C	0.96
C9—C10	1.382 (3)	C23—N3	1.449 (2)
C9—H9	0.93	C23—H23A	0.96
C10—C11	1.377 (2)	C23—H23B	0.96
C10—H10	0.93	C23—H23C	0.96
C12—C13	1.495 (3)	C24—N2	1.457 (2)
C12—H12A	0.97	C24—H24A	0.96
C12—H12B	0.97	C24—H24B	0.96
C13—O3	1.206 (2)	C24—H24C	0.96
N2—C1—C11	114.62 (14)	O2—C14—C2	127.58 (17)
N2—C1—C5	113.10 (14)	N3—C14—C2	108.69 (15)
C11—C1—C5	100.82 (13)	C20—C15—C16	117.38 (16)
N2—C1—C2	102.35 (13)	C20—C15—C3	123.29 (16)
C11—C1—C2	116.31 (14)	C16—C15—C3	119.33 (16)
C5—C1—C2	110.02 (13)	C17—C16—C15	121.32 (17)
C14—C2—C12	101.07 (14)	C17—C16—H16	119.3
C14—C2—C3	109.14 (14)	C15—C16—H16	119.3
C12—C2—C3	120.23 (14)	C16—C17—C18	120.32 (17)
C14—C2—C1	108.66 (13)	C16—C17—H17	119.8
C12—C2—C1	113.20 (13)	C18—C17—H17	119.8
C3—C2—C1	104.19 (13)	O4—C18—C19	124.61 (17)
C15—C3—C4	115.57 (15)	O4—C18—C17	115.98 (16)
C15—C3—C2	116.42 (14)	C19—C18—C17	119.41 (17)
C4—C3—C2	104.44 (13)	C18—C19—C20	119.84 (18)
C15—C3—H3	106.6	C18—C19—H19	120.1
C4—C3—H3	106.6	C20—C19—H19	120.1
C2—C3—H3	106.6	C15—C20—C19	121.69 (17)
N2—C4—C3	103.73 (14)	C15—C20—H20	119.2
N2—C4—H4A	111.0	C19—C20—H20	119.2
C3—C4—H4A	111.0	O4—C21—H21A	109.5
N2—C4—H4B	111.0	O4—C21—H21B	109.5
C3—C4—H4B	111.0	H21A—C21—H21B	109.5
H4A—C4—H4B	109.0	O4—C21—H21C	109.5
O1—C5—N1	124.84 (17)	H21A—C21—H21C	109.5
O1—C5—C1	126.55 (16)	H21B—C21—H21C	109.5
N1—C5—C1	108.61 (15)	N1—C22—H22A	109.5
C7—C6—C11	122.24 (18)	N1—C22—H22B	109.5
C7—C6—N1	127.72 (18)	H22A—C22—H22B	109.5
C11—C6—N1	110.04 (15)	N1—C22—H22C	109.5
C6—C7—C8	117.1 (2)	H22A—C22—H22C	109.5
C6—C7—H7	121.5	H22B—C22—H22C	109.5
C8—C7—H7	121.5	N3—C23—H23A	109.5
C9—C8—C7	121.5 (2)	N3—C23—H23B	109.5
C9—C8—H8	119.3	H23A—C23—H23B	109.5
C7—C8—H8	119.3	N3—C23—H23C	109.5
C8—C9—C10	120.6 (2)	H23A—C23—H23C	109.5
C8—C9—H9	119.7	H23B—C23—H23C	109.5
C10—C9—H9	119.7	N2—C24—H24A	109.5
C11—C10—C9	118.96 (19)	N2—C24—H24B	109.5
C11—C10—H10	120.5	H24A—C24—H24B	109.5
C9—C10—H10	120.5	N2—C24—H24C	109.5
C10—C11—C6	119.59 (17)	H24A—C24—H24C	109.5
C10—C11—C1	131.08 (17)	H24B—C24—H24C	109.5
C6—C11—C1	109.33 (15)	C5—N1—C6	111.01 (15)
C13—C12—C2	104.72 (14)	C5—N1—C22	123.85 (17)
C13—C12—H12A	110.8	C6—N1—C22	125.11 (16)
C2—C12—H12A	110.8	C1—N2—C24	115.17 (15)
C13—C12—H12B	110.8	C1—N2—C4	106.52 (13)
C2—C12—H12B	110.8	C24—N2—C4	113.80 (15)
H12A—C12—H12B	108.9	C13—N3—C14	112.41 (15)
O3—C13—N3	124.28 (19)	C13—N3—C23	123.79 (17)
O3—C13—C12	128.21 (18)	C14—N3—C23	123.66 (16)
N3—C13—C12	107.50 (16)	C18—O4—C21	118.25 (16)
O2—C14—N3	123.71 (17)
N2—C1—C2—C14	93.48 (15)	C3—C2—C14—O2	35.9 (2)
C11—C1—C2—C14	−32.26 (19)	C1—C2—C14—O2	−77.1 (2)
C5—C1—C2—C14	−146.03 (14)	C12—C2—C14—N3	−17.91 (17)
N2—C1—C2—C12	−155.10 (13)	C3—C2—C14—N3	−145.57 (14)
C11—C1—C2—C12	79.16 (18)	C1—C2—C14—N3	101.41 (15)
C5—C1—C2—C12	−34.61 (18)	C4—C3—C15—C20	−52.9 (2)
N2—C1—C2—C3	−22.77 (15)	C2—C3—C15—C20	70.3 (2)
C11—C1—C2—C3	−148.51 (14)	C4—C3—C15—C16	127.21 (18)
C5—C1—C2—C3	97.71 (15)	C2—C3—C15—C16	−109.68 (18)
C14—C2—C3—C15	113.00 (16)	C20—C15—C16—C17	−1.2 (3)
C12—C2—C3—C15	−2.9 (2)	C3—C15—C16—C17	178.77 (17)
C1—C2—C3—C15	−131.08 (15)	C15—C16—C17—C18	−0.7 (3)
C14—C2—C3—C4	−118.28 (15)	C16—C17—C18—O4	−178.00 (17)
C12—C2—C3—C4	125.78 (16)	C16—C17—C18—C19	2.2 (3)
C1—C2—C3—C4	−2.36 (17)	O4—C18—C19—C20	178.42 (18)
C15—C3—C4—N2	155.96 (14)	C17—C18—C19—C20	−1.8 (3)
C2—C3—C4—N2	26.73 (18)	C16—C15—C20—C19	1.6 (3)
N2—C1—C5—O1	52.8 (2)	C3—C15—C20—C19	−178.35 (18)
C11—C1—C5—O1	175.67 (18)	C18—C19—C20—C15	−0.1 (3)
C2—C1—C5—O1	−61.0 (2)	O1—C5—N1—C6	−177.45 (18)
N2—C1—C5—N1	−126.61 (16)	C1—C5—N1—C6	2.0 (2)
C11—C1—C5—N1	−3.74 (18)	O1—C5—N1—C22	0.8 (3)
C2—C1—C5—N1	119.62 (15)	C1—C5—N1—C22	−179.82 (17)
C11—C6—C7—C8	0.0 (3)	C7—C6—N1—C5	−179.8 (2)
N1—C6—C7—C8	−179.1 (2)	C11—C6—N1—C5	0.9 (2)
C6—C7—C8—C9	2.0 (4)	C7—C6—N1—C22	2.0 (3)
C7—C8—C9—C10	−1.5 (4)	C11—C6—N1—C22	−177.27 (18)
C8—C9—C10—C11	−1.1 (3)	C11—C1—N2—C24	−64.5 (2)
C9—C10—C11—C6	3.1 (3)	C5—C1—N2—C24	50.3 (2)
C9—C10—C11—C1	−176.66 (19)	C2—C1—N2—C24	168.64 (14)
C7—C6—C11—C10	−2.6 (3)	C11—C1—N2—C4	168.29 (15)
N1—C6—C11—C10	176.70 (16)	C5—C1—N2—C4	−76.88 (17)
C7—C6—C11—C1	177.21 (18)	C2—C1—N2—C4	41.45 (16)
N1—C6—C11—C1	−3.5 (2)	C3—C4—N2—C1	−43.87 (18)
N2—C1—C11—C10	−54.1 (3)	C3—C4—N2—C24	−171.88 (15)
C5—C1—C11—C10	−175.93 (19)	O3—C13—N3—C14	−170.56 (18)
C2—C1—C11—C10	65.2 (2)	C12—C13—N3—C14	10.2 (2)
N2—C1—C11—C6	126.08 (16)	O3—C13—N3—C23	5.3 (3)
C5—C1—C11—C6	4.28 (18)	C12—C13—N3—C23	−174.00 (18)
C2—C1—C11—C6	−114.63 (16)	O2—C14—N3—C13	−175.89 (17)
C14—C2—C12—C13	22.91 (17)	C2—C14—N3—C13	5.5 (2)
C3—C2—C12—C13	142.96 (15)	O2—C14—N3—C23	8.3 (3)
C1—C2—C12—C13	−93.10 (16)	C2—C14—N3—C23	−170.30 (17)
C2—C12—C13—O3	159.54 (19)	C19—C18—O4—C21	−5.5 (3)
C2—C12—C13—N3	−21.23 (19)	C17—C18—O4—C21	174.65 (18)
C12—C2—C14—O2	163.58 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2	0.93	2.52	3.122 (2)	123
C12—H12A···O1	0.97	2.58	3.222 (2)	124
C20—H20···O1	0.93	2.56	3.400 (2)	150
C12—H12B···O1i	0.97	2.56	3.264 (2)	129
C16—H16···O4ii	0.93	2.50	3.394 (2)	161
C19—H19···O2iii	0.93	2.54	3.440 (2)	162
C21—H21C···Cg1iv	0.96	2.93	3.592 (2)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2	0.93	2.52	3.122 (2)	123
C12—H12A⋯O1	0.97	2.58	3.222 (2)	124
C20—H20⋯O1	0.93	2.56	3.400 (2)	150
C12—H12B⋯O1i	0.97	2.56	3.264 (2)	129
C16—H16⋯O4ii	0.93	2.50	3.394 (2)	161
C19—H19⋯O2iii	0.93	2.54	3.440 (2)	162
C21—H21C⋯Cg1iv	0.96	2.93	3.592 (2)	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C15–C20 ring.