4'-(3-Bromo-phen-yl)-1'-methyl-dispiro-[indan-2,2'-pyrrolidine-3',2''-indan]-1,3,1''-trione.

In the title compound, C(27)H(20)BrNO(3), two intra-molecular C-H⋯O hydrogen bonds both form S(6) rings. The pyrrolidine ring adopts a twisted conformation about the C-C bond bearing the indane ring systems. The other two five-membered rings within the indane systems are in shallow envelope conformations, with the spiro C atoms as the flap atoms. The mean plane of the pyrrolidine ring [maximum deviation = 0.275 (1) Å] makes dihedral angles of 65.25 (7), 78.33 (6) and 75.25 (6)° with the bromo-substituted benzene ring and the mean planes of the mono- and dioxo-substituted indane rings, respectively. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯N hydrogen bonds into a three-dimensional network. In addition, C-H⋯π inter-actions are observed.

Related literature

For related structures and medicinal background, see: Wei et al. (2011 ▶, 2012a ▶,b ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C27H20BrNO3

M = 486.35

Triclinic,

a = 8.3998 (1) Å

b = 11.2082 (2) Å

c = 12.4816 (2) Å

α = 112.004 (1)°

β = 96.850 (1)°

γ = 93.191 (1)°

V = 1075.28 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.94 mm−1

T = 100 K

0.51 × 0.31 × 0.29 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.436, T max = 0.599

23814 measured reflections

6318 independent reflections

5810 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.075

S = 1.04

6318 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.53 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 datablock(s) global, I. DOI: 10.1107/S1600536812037993/hb6949sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037993/hb6949Isup2.hkl

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

C27H20BrNO3	Z = 2
Mr = 486.35	F(000) = 496
Triclinic, P1	Dx = 1.502 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3998 (1) Å	Cell parameters from 9917 reflections
b = 11.2082 (2) Å	θ = 3.0–30.1°
c = 12.4816 (2) Å	µ = 1.94 mm−1
α = 112.004 (1)°	T = 100 K
β = 96.850 (1)°	Block, yellow
γ = 93.191 (1)°	0.51 × 0.31 × 0.29 mm
V = 1075.28 (3) Å3

Bruker SMART APEXII CCD diffractometer	6318 independent reflections
Radiation source: fine-focus sealed tube	5810 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 30.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.436, Tmax = 0.599	k = −15→15
23814 measured reflections	l = −17→17

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0394P)2 + 0.5548P] where P = (Fo2 + 2Fc2)/3
6318 reflections	(Δ/σ)max = 0.001
290 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.53 e Å−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 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
Br1	0.225327 (19)	−0.034338 (13)	0.491671 (13)	0.02629 (5)
O1	0.13721 (12)	0.70139 (9)	1.01601 (8)	0.01768 (18)
O2	−0.06941 (12)	0.68997 (9)	0.64765 (8)	0.01841 (18)
O3	0.45101 (11)	0.66808 (9)	0.88616 (8)	0.01675 (18)
N1	−0.05884 (13)	0.52853 (10)	0.78612 (9)	0.01380 (19)
C1	0.12730 (14)	0.72671 (12)	0.92921 (10)	0.0133 (2)
C2	0.15991 (15)	0.85606 (12)	0.92485 (11)	0.0147 (2)
C3	0.24222 (17)	0.96921 (13)	1.01069 (12)	0.0197 (3)
H3A	0.2879	0.9714	1.0849	0.024*
C4	0.25502 (19)	1.07871 (13)	0.98385 (12)	0.0233 (3)
H4A	0.3133	1.1565	1.0398	0.028*
C5	0.18338 (19)	1.07629 (13)	0.87559 (13)	0.0226 (3)
H5A	0.1907	1.1534	0.8606	0.027*
C6	0.10196 (17)	0.96343 (13)	0.78980 (12)	0.0188 (2)
H6A	0.0534	0.9617	0.7164	0.023*
C7	0.09426 (15)	0.85257 (12)	0.81561 (11)	0.0144 (2)
C8	0.01860 (14)	0.72063 (12)	0.73996 (11)	0.0134 (2)
C9	0.06749 (14)	0.62884 (11)	0.80214 (10)	0.0118 (2)
C10	0.20794 (14)	0.54710 (11)	0.75111 (10)	0.0117 (2)
C11	0.37225 (14)	0.63118 (11)	0.78907 (11)	0.0128 (2)
C12	0.41207 (14)	0.65657 (12)	0.68743 (10)	0.0128 (2)
C13	0.53931 (15)	0.73898 (12)	0.68183 (11)	0.0152 (2)
H13A	0.6138	0.7891	0.7497	0.018*
C14	0.55375 (16)	0.74547 (13)	0.57472 (12)	0.0172 (2)
H14A	0.6395	0.8002	0.5683	0.021*
C15	0.44190 (16)	0.67141 (13)	0.47562 (11)	0.0172 (2)
H15A	0.4525	0.6778	0.4030	0.021*
C16	0.31575 (15)	0.58883 (12)	0.48106 (11)	0.0152 (2)
H16A	0.2412	0.5388	0.4132	0.018*
C17	0.30179 (14)	0.58155 (11)	0.58869 (10)	0.0126 (2)
C18	0.18261 (15)	0.49507 (12)	0.61636 (10)	0.0129 (2)
H18A	0.2052	0.4037	0.5829	0.016*
H18B	0.0707	0.5013	0.5852	0.016*
C19	0.19356 (15)	0.44614 (12)	0.80828 (11)	0.0137 (2)
H19A	0.2382	0.4924	0.8930	0.016*
C20	0.01072 (16)	0.41788 (13)	0.80165 (13)	0.0186 (2)
H20A	−0.0317	0.3363	0.7348	0.022*
H20B	−0.0147	0.4104	0.8745	0.022*
C21	0.28456 (15)	0.32899 (12)	0.76277 (11)	0.0141 (2)
C22	0.43223 (16)	0.32640 (13)	0.82660 (12)	0.0183 (2)
H22A	0.4753	0.3995	0.8952	0.022*
C23	0.51708 (17)	0.21825 (15)	0.79110 (14)	0.0230 (3)
H23A	0.6175	0.2186	0.8353	0.028*
C24	0.45598 (17)	0.11009 (14)	0.69174 (14)	0.0224 (3)
H24A	0.5124	0.0356	0.6678	0.027*
C25	0.31020 (17)	0.11346 (12)	0.62810 (12)	0.0182 (2)
C26	0.22394 (15)	0.22029 (12)	0.66123 (11)	0.0156 (2)
H26A	0.1248	0.2198	0.6156	0.019*
C27	−0.19926 (16)	0.56775 (13)	0.84332 (12)	0.0185 (2)
H27A	−0.2416	0.6379	0.8236	0.028*
H27B	−0.1682	0.5980	0.9282	0.028*
H27C	−0.2825	0.4938	0.8167	0.028*

	U11	U22	U33	U12	U13	U23
Br1	0.03101 (9)	0.01684 (7)	0.02711 (8)	0.00156 (5)	0.01300 (6)	0.00162 (5)
O1	0.0203 (4)	0.0199 (4)	0.0145 (4)	0.0010 (4)	0.0044 (3)	0.0082 (4)
O2	0.0171 (4)	0.0200 (4)	0.0177 (4)	0.0007 (3)	−0.0005 (3)	0.0080 (4)
O3	0.0142 (4)	0.0212 (4)	0.0140 (4)	−0.0012 (3)	0.0008 (3)	0.0067 (3)
N1	0.0116 (4)	0.0132 (4)	0.0174 (5)	−0.0003 (4)	0.0051 (4)	0.0062 (4)
C1	0.0120 (5)	0.0145 (5)	0.0135 (5)	0.0006 (4)	0.0039 (4)	0.0052 (4)
C2	0.0161 (5)	0.0141 (5)	0.0140 (5)	0.0001 (4)	0.0048 (4)	0.0051 (4)
C3	0.0250 (7)	0.0161 (6)	0.0157 (6)	−0.0022 (5)	0.0023 (5)	0.0045 (5)
C4	0.0316 (7)	0.0152 (6)	0.0200 (6)	−0.0049 (5)	0.0047 (5)	0.0041 (5)
C5	0.0326 (7)	0.0151 (6)	0.0222 (6)	−0.0016 (5)	0.0081 (5)	0.0088 (5)
C6	0.0236 (6)	0.0172 (6)	0.0179 (6)	0.0008 (5)	0.0059 (5)	0.0088 (5)
C7	0.0145 (5)	0.0141 (5)	0.0150 (5)	0.0004 (4)	0.0044 (4)	0.0057 (4)
C8	0.0121 (5)	0.0149 (5)	0.0148 (5)	0.0016 (4)	0.0044 (4)	0.0069 (4)
C9	0.0119 (5)	0.0124 (5)	0.0117 (5)	−0.0003 (4)	0.0030 (4)	0.0051 (4)
C10	0.0110 (5)	0.0126 (5)	0.0118 (5)	−0.0006 (4)	0.0029 (4)	0.0050 (4)
C11	0.0115 (5)	0.0129 (5)	0.0143 (5)	0.0011 (4)	0.0039 (4)	0.0050 (4)
C12	0.0120 (5)	0.0141 (5)	0.0135 (5)	0.0014 (4)	0.0034 (4)	0.0062 (4)
C13	0.0130 (5)	0.0160 (5)	0.0168 (5)	−0.0006 (4)	0.0026 (4)	0.0066 (4)
C14	0.0160 (6)	0.0177 (5)	0.0203 (6)	−0.0007 (4)	0.0060 (5)	0.0094 (5)
C15	0.0186 (6)	0.0201 (6)	0.0166 (5)	0.0023 (5)	0.0065 (4)	0.0102 (5)
C16	0.0154 (5)	0.0169 (5)	0.0138 (5)	0.0003 (4)	0.0035 (4)	0.0063 (4)
C17	0.0125 (5)	0.0129 (5)	0.0137 (5)	0.0014 (4)	0.0042 (4)	0.0058 (4)
C18	0.0133 (5)	0.0140 (5)	0.0112 (5)	−0.0018 (4)	0.0026 (4)	0.0048 (4)
C19	0.0157 (5)	0.0136 (5)	0.0140 (5)	0.0011 (4)	0.0048 (4)	0.0069 (4)
C20	0.0171 (6)	0.0155 (5)	0.0280 (7)	0.0027 (4)	0.0109 (5)	0.0114 (5)
C21	0.0150 (5)	0.0147 (5)	0.0157 (5)	0.0014 (4)	0.0053 (4)	0.0084 (4)
C22	0.0161 (6)	0.0201 (6)	0.0205 (6)	0.0007 (5)	0.0022 (5)	0.0101 (5)
C23	0.0160 (6)	0.0273 (7)	0.0309 (7)	0.0049 (5)	0.0034 (5)	0.0167 (6)
C24	0.0211 (6)	0.0215 (6)	0.0313 (7)	0.0083 (5)	0.0116 (5)	0.0148 (6)
C25	0.0204 (6)	0.0148 (5)	0.0208 (6)	0.0015 (5)	0.0092 (5)	0.0067 (5)
C26	0.0163 (5)	0.0160 (5)	0.0168 (5)	0.0020 (4)	0.0052 (4)	0.0081 (5)
C27	0.0138 (5)	0.0205 (6)	0.0226 (6)	0.0018 (4)	0.0074 (5)	0.0084 (5)

Br1—C25	1.9019 (14)	C13—H13A	0.9500
O1—C1	1.2135 (15)	C14—C15	1.4030 (18)
O2—C8	1.2100 (15)	C14—H14A	0.9500
O3—C11	1.2165 (15)	C15—C16	1.3925 (17)
N1—C9	1.4416 (15)	C15—H15A	0.9500
N1—C27	1.4553 (16)	C16—C17	1.3943 (16)
N1—C20	1.4665 (16)	C16—H16A	0.9500
C1—C2	1.4827 (17)	C17—C18	1.5120 (16)
C1—C9	1.5544 (17)	C18—H18A	0.9900
C2—C3	1.3935 (17)	C18—H18B	0.9900
C2—C7	1.3939 (17)	C19—C21	1.5123 (17)
C3—C4	1.3900 (19)	C19—C20	1.5369 (18)
C3—H3A	0.9500	C19—H19A	1.0000
C4—C5	1.402 (2)	C20—H20A	0.9900
C4—H4A	0.9500	C20—H20B	0.9900
C5—C6	1.3887 (19)	C21—C22	1.4000 (18)
C5—H5A	0.9500	C21—C26	1.4035 (18)
C6—C7	1.3956 (17)	C22—C23	1.3938 (19)
C6—H6A	0.9500	C22—H22A	0.9500
C7—C8	1.4793 (17)	C23—C24	1.387 (2)
C8—C9	1.5488 (16)	C23—H23A	0.9500
C9—C10	1.5809 (17)	C24—C25	1.388 (2)
C10—C18	1.5427 (16)	C24—H24A	0.9500
C10—C11	1.5434 (16)	C25—C26	1.3881 (18)
C10—C19	1.5540 (16)	C26—H26A	0.9500
C11—C12	1.4708 (16)	C27—H27A	0.9800
C12—C17	1.3959 (17)	C27—H27B	0.9800
C12—C13	1.3988 (16)	C27—H27C	0.9800
C13—C14	1.3849 (17)
C9—N1—C27	117.31 (10)	C16—C15—C14	121.67 (11)
C9—N1—C20	110.09 (10)	C16—C15—H15A	119.2
C27—N1—C20	115.37 (10)	C14—C15—H15A	119.2
O1—C1—C2	126.85 (11)	C15—C16—C17	118.25 (11)
O1—C1—C9	125.46 (11)	C15—C16—H16A	120.9
C2—C1—C9	107.59 (10)	C17—C16—H16A	120.9
C3—C2—C7	121.15 (11)	C16—C17—C12	119.94 (11)
C3—C2—C1	129.27 (11)	C16—C17—C18	128.53 (11)
C7—C2—C1	109.57 (11)	C12—C17—C18	111.46 (10)
C4—C3—C2	117.60 (13)	C17—C18—C10	104.24 (9)
C4—C3—H3A	121.2	C17—C18—H18A	110.9
C2—C3—H3A	121.2	C10—C18—H18A	110.9
C3—C4—C5	121.12 (13)	C17—C18—H18B	110.9
C3—C4—H4A	119.4	C10—C18—H18B	110.9
C5—C4—H4A	119.4	H18A—C18—H18B	108.9
C6—C5—C4	121.28 (12)	C21—C19—C20	115.88 (10)
C6—C5—H5A	119.4	C21—C19—C10	116.93 (10)
C4—C5—H5A	119.4	C20—C19—C10	103.69 (10)
C5—C6—C7	117.38 (12)	C21—C19—H19A	106.5
C5—C6—H6A	121.3	C20—C19—H19A	106.5
C7—C6—H6A	121.3	C10—C19—H19A	106.5
C2—C7—C6	121.37 (12)	N1—C20—C19	105.19 (10)
C2—C7—C8	110.26 (10)	N1—C20—H20A	110.7
C6—C7—C8	128.36 (11)	C19—C20—H20A	110.7
O2—C8—C7	126.41 (11)	N1—C20—H20B	110.7
O2—C8—C9	125.88 (11)	C19—C20—H20B	110.7
C7—C8—C9	107.69 (10)	H20A—C20—H20B	108.8
N1—C9—C8	113.45 (10)	C22—C21—C26	118.48 (12)
N1—C9—C1	117.20 (10)	C22—C21—C19	118.89 (11)
C8—C9—C1	101.52 (9)	C26—C21—C19	122.59 (11)
N1—C9—C10	101.75 (9)	C23—C22—C21	121.04 (13)
C8—C9—C10	113.18 (9)	C23—C22—H22A	119.5
C1—C9—C10	110.18 (9)	C21—C22—H22A	119.5
C18—C10—C11	104.54 (9)	C24—C23—C22	120.48 (13)
C18—C10—C19	117.18 (10)	C24—C23—H23A	119.8
C11—C10—C19	113.68 (10)	C22—C23—H23A	119.8
C18—C10—C9	111.30 (9)	C23—C24—C25	118.31 (13)
C11—C10—C9	111.58 (9)	C23—C24—H24A	120.8
C19—C10—C9	98.74 (9)	C25—C24—H24A	120.8
O3—C11—C12	127.83 (11)	C26—C25—C24	122.29 (13)
O3—C11—C10	124.83 (11)	C26—C25—Br1	119.05 (10)
C12—C11—C10	107.34 (10)	C24—C25—Br1	118.66 (10)
C17—C12—C13	121.81 (11)	C25—C26—C21	119.40 (12)
C17—C12—C11	109.50 (10)	C25—C26—H26A	120.3
C13—C12—C11	128.68 (11)	C21—C26—H26A	120.3
C14—C13—C12	118.21 (11)	N1—C27—H27A	109.5
C14—C13—H13A	120.9	N1—C27—H27B	109.5
C12—C13—H13A	120.9	H27A—C27—H27B	109.5
C13—C14—C15	120.12 (12)	N1—C27—H27C	109.5
C13—C14—H14A	119.9	H27A—C27—H27C	109.5
C15—C14—H14A	119.9	H27B—C27—H27C	109.5
O1—C1—C2—C3	16.5 (2)	C9—C10—C11—O3	75.27 (15)
C9—C1—C2—C3	−166.90 (13)	C18—C10—C11—C12	15.76 (12)
O1—C1—C2—C7	−163.84 (13)	C19—C10—C11—C12	144.75 (10)
C9—C1—C2—C7	12.81 (14)	C9—C10—C11—C12	−104.65 (11)
C7—C2—C3—C4	0.6 (2)	O3—C11—C12—C17	171.44 (12)
C1—C2—C3—C4	−179.67 (13)	C10—C11—C12—C17	−8.65 (13)
C2—C3—C4—C5	1.9 (2)	O3—C11—C12—C13	−7.4 (2)
C3—C4—C5—C6	−2.3 (2)	C10—C11—C12—C13	172.53 (12)
C4—C5—C6—C7	0.0 (2)	C17—C12—C13—C14	0.34 (19)
C3—C2—C7—C6	−3.0 (2)	C11—C12—C13—C14	179.03 (12)
C1—C2—C7—C6	177.30 (12)	C12—C13—C14—C15	0.47 (19)
C3—C2—C7—C8	178.12 (12)	C13—C14—C15—C16	−0.9 (2)
C1—C2—C7—C8	−1.62 (14)	C14—C15—C16—C17	0.40 (19)
C5—C6—C7—C2	2.6 (2)	C15—C16—C17—C12	0.41 (18)
C5—C6—C7—C8	−178.72 (13)	C15—C16—C17—C18	−176.36 (12)
C2—C7—C8—O2	167.84 (13)	C13—C12—C17—C16	−0.79 (18)
C6—C7—C8—O2	−11.0 (2)	C11—C12—C17—C16	−179.71 (11)
C2—C7—C8—C9	−10.25 (14)	C13—C12—C17—C18	176.50 (11)
C6—C7—C8—C9	170.92 (13)	C11—C12—C17—C18	−2.42 (14)
C27—N1—C9—C8	−69.28 (14)	C16—C17—C18—C10	−170.69 (12)
C20—N1—C9—C8	156.11 (10)	C12—C17—C18—C10	12.31 (13)
C27—N1—C9—C1	48.61 (15)	C11—C10—C18—C17	−16.54 (12)
C20—N1—C9—C1	−86.00 (13)	C19—C10—C18—C17	−143.39 (10)
C27—N1—C9—C10	168.82 (10)	C9—C10—C18—C17	104.06 (11)
C20—N1—C9—C10	34.20 (12)	C18—C10—C19—C21	48.01 (15)
O2—C8—C9—N1	−34.63 (17)	C11—C10—C19—C21	−74.23 (13)
C7—C8—C9—N1	143.47 (10)	C9—C10—C19—C21	167.49 (10)
O2—C8—C9—C1	−161.28 (12)	C18—C10—C19—C20	−80.86 (12)
C7—C8—C9—C1	16.82 (12)	C11—C10—C19—C20	156.90 (10)
O2—C8—C9—C10	80.66 (15)	C9—C10—C19—C20	38.62 (11)
C7—C8—C9—C10	−101.24 (11)	C9—N1—C20—C19	−9.38 (14)
O1—C1—C9—N1	34.79 (18)	C27—N1—C20—C19	−144.95 (11)
C2—C1—C9—N1	−141.92 (11)	C21—C19—C20—N1	−149.54 (10)
O1—C1—C9—C8	158.94 (12)	C10—C19—C20—N1	−20.02 (13)
C2—C1—C9—C8	−17.76 (12)	C20—C19—C21—C22	−136.87 (12)
O1—C1—C9—C10	−80.86 (15)	C10—C19—C21—C22	100.35 (13)
C2—C1—C9—C10	102.43 (11)	C20—C19—C21—C26	40.61 (16)
N1—C9—C10—C18	79.65 (11)	C10—C19—C21—C26	−82.17 (15)
C8—C9—C10—C18	−42.44 (13)	C26—C21—C22—C23	−0.50 (19)
C1—C9—C10—C18	−155.32 (9)	C19—C21—C22—C23	177.08 (12)
N1—C9—C10—C11	−163.99 (9)	C21—C22—C23—C24	−0.5 (2)
C8—C9—C10—C11	73.92 (12)	C22—C23—C24—C25	1.0 (2)
C1—C9—C10—C11	−38.96 (12)	C23—C24—C25—C26	−0.6 (2)
N1—C9—C10—C19	−44.13 (10)	C23—C24—C25—Br1	179.99 (10)
C8—C9—C10—C19	−166.22 (10)	C24—C25—C26—C21	−0.34 (19)
C1—C9—C10—C19	80.89 (11)	Br1—C25—C26—C21	179.05 (9)
C18—C10—C11—O3	−164.32 (12)	C22—C21—C26—C25	0.89 (18)
C19—C10—C11—O3	−35.33 (17)	C19—C21—C26—C25	−176.60 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O2	0.99	2.39	3.0787 (17)	126
C19—H19A···O1	1.00	2.53	3.1649 (17)	121
C4—H4A···O3i	0.95	2.53	3.4056 (18)	153
C16—H16A···N1ii	0.95	2.58	3.4912 (16)	161
C20—H20B···O1iii	0.99	2.44	3.3586 (18)	153
C23—H23A···O1iv	0.95	2.48	3.3847 (18)	160
C5—H5A···Cg1v	0.95	2.65	3.3386 (17)	130
C15—H15A···Cg1vi	0.95	2.82	3.6623 (15)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C21–C26 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18B⋯O2	0.99	2.39	3.0787 (17)	126
C19—H19A⋯O1	1.00	2.53	3.1649 (17)	121
C4—H4A⋯O3i	0.95	2.53	3.4056 (18)	153
C16—H16A⋯N1ii	0.95	2.58	3.4912 (16)	161
C20—H20B⋯O1iii	0.99	2.44	3.3586 (18)	153
C23—H23A⋯O1iv	0.95	2.48	3.3847 (18)	160
C5—H5A⋯Cg1v	0.95	2.65	3.3386 (17)	130
C15—H15A⋯Cg1vi	0.95	2.82	3.6623 (15)	149

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .