3-Ethyl-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexahydro-1H-pyrrolo[3,4-b]quinoline.

In the mol-ecule of the title compound, C(26)H(28)N(2)O(2)S, the pyrrolidine ring adopts an envelope conformation and the tetra-hydro-pyridine ring is in a half-chair conformation; these two rings are trans-fused. The dihedral angle between the pyridine- and sulfonyl-bound benzene rings is 36.15 (5)°. In the crystalline state, the mol-ecules are linked into a two-dimensional network parallel to the ab plane by C-H⋯O and C-H⋯π inter-actions.

Related literature

For the orientations of phenyl and ethyl substituents with respect to the fused ring system in the related 7-chloro- and 7-bromo-derivatives, see: Sudha et al. (2007 ▶, 2008 ▶). For biological activities of pyrrolo[3,4-b]quinoline derivatives, see: Anzini et al. (1990 ▶, 1992 ▶); Crenshaw et al. (1976 ▶); Fujita et al. (1996 ▶); Xiao et al. (2006 ▶). For related literature, see: Duax et al. (1976 ▶); Cremer & Pople (1975 ▶).

Experimental

Crystal data

C26H28N2O2S

M = 432.56

Triclinic,

a = 9.3990 (1) Å

b = 10.9077 (2) Å

c = 12.5654 (3) Å

α = 64.3190 (8)°

β = 72.5291 (8)°

γ = 76.3803 (8)°

V = 1099.07 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 100.0 (1) K

0.48 × 0.37 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.878, T max = 0.971

49024 measured reflections

11697 independent reflections

9445 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.122

S = 1.03

11697 reflections

285 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Version 5.1; Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000482/rz2188sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000482/rz2188Isup2.hkl

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

C26H28N2O2S	Z = 2
Mr = 432.56	F000 = 460
Triclinic, P1	Dx = 1.307 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.3990 (1) Å	Cell parameters from 7071 reflections
b = 10.9077 (2) Å	θ = 2.2–37.7º
c = 12.5654 (3) Å	µ = 0.17 mm−1
α = 64.3190 (8)º	T = 100.0 (1) K
β = 72.5291 (8)º	Block, colourless
γ = 76.3803 (8)º	0.48 × 0.37 × 0.17 mm
V = 1099.07 (4) Å3

Bruker APEXII CCD area-detector diffractometer	11697 independent reflections
Radiation source: fine-focus sealed tube	9445 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.038
Detector resolution: 8.33 pixels mm-1	θmax = 37.8º
T = 100.0(1) K	θmin = 1.9º
ω scans	h = −15→16
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −18→18
Tmin = 0.878, Tmax = 0.971	l = −21→21
49024 measured reflections

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0632P)2 + 0.2032P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
11697 reflections	Δρmax = 0.54 e Å−3
285 parameters	Δρmin = −0.47 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
S1	0.49683 (2)	0.424122 (19)	0.278537 (17)	0.01327 (5)
O1	0.35740 (7)	0.37308 (7)	0.30453 (6)	0.01740 (11)
O2	0.49608 (8)	0.55466 (6)	0.28077 (6)	0.01737 (11)
N1	0.59007 (8)	0.30981 (7)	0.37860 (6)	0.01346 (11)
N2	0.99769 (8)	0.23374 (7)	0.33005 (7)	0.01746 (13)
H1N2	1.0420 (18)	0.2777 (15)	0.3524 (14)	0.034 (4)*
C1	0.61499 (9)	0.16668 (8)	0.38536 (7)	0.01513 (13)
H1A	0.5572	0.1571	0.3377	0.018*
H1B	0.5887	0.1016	0.4685	0.018*
C2	0.78261 (9)	0.14729 (7)	0.33219 (7)	0.01321 (12)
H2	0.8007	0.2038	0.2451	0.016*
C3	0.86315 (9)	0.00361 (8)	0.34922 (7)	0.01390 (12)
H3	0.8397	−0.0548	0.4359	0.017*
C4	1.03201 (9)	0.01342 (8)	0.30922 (7)	0.01426 (12)
C5	1.13274 (10)	−0.08705 (8)	0.27522 (8)	0.01671 (13)
H5	1.0951	−0.1589	0.2757	0.020*
C6	1.28696 (10)	−0.08326 (9)	0.24074 (8)	0.01913 (15)
H6	1.3514	−0.1511	0.2179	0.023*
C7	1.34377 (11)	0.02374 (9)	0.24084 (9)	0.02159 (16)
H7	1.4469	0.0269	0.2193	0.026*
C8	1.24635 (10)	0.12555 (9)	0.27314 (9)	0.02058 (15)
H8	1.2851	0.1966	0.2730	0.025*
C9	1.09059 (9)	0.12303 (8)	0.30597 (7)	0.01567 (13)
C10	0.84289 (9)	0.21313 (8)	0.39204 (7)	0.01400 (12)
H10	0.8370	0.1535	0.4778	0.017*
C11	0.73416 (9)	0.34598 (8)	0.38053 (7)	0.01333 (12)
H11	0.7704	0.4197	0.3031	0.016*
C12	0.60265 (9)	0.42650 (8)	0.13594 (7)	0.01398 (12)
C13	0.71831 (10)	0.50922 (8)	0.07365 (7)	0.01698 (14)
H13	0.7306	0.5714	0.1016	0.020*
C14	0.81489 (11)	0.49778 (9)	−0.03058 (8)	0.01997 (15)
H14	0.8916	0.5533	−0.0727	0.024*
C15	0.79834 (11)	0.40407 (9)	−0.07292 (7)	0.01950 (15)
C16	0.67845 (11)	0.32643 (9)	−0.01229 (7)	0.01902 (15)
H16	0.6639	0.2667	−0.0420	0.023*
C17	0.58026 (10)	0.33691 (8)	0.09193 (7)	0.01663 (13)
H17	0.5006	0.2847	0.1318	0.020*
C18	0.90773 (13)	0.38731 (12)	−0.18222 (9)	0.0290 (2)
H18A	0.9524	0.2936	−0.1608	0.044*
H18B	0.9849	0.4455	−0.2104	0.044*
H18C	0.8558	0.4122	−0.2452	0.044*
C19	0.81012 (9)	−0.05736 (8)	0.28198 (7)	0.01477 (13)
C20	0.83943 (11)	−0.00052 (9)	0.15531 (8)	0.01856 (14)
H20	0.8949	0.0734	0.1120	0.022*
C21	0.78685 (12)	−0.05303 (10)	0.09319 (9)	0.02300 (17)
H21	0.8071	−0.0142	0.0089	0.028*
C22	0.70390 (12)	−0.16372 (10)	0.15726 (11)	0.02572 (19)
H22	0.6683	−0.1987	0.1159	0.031*
C23	0.67453 (11)	−0.22161 (9)	0.28268 (11)	0.02484 (18)
H23	0.6191	−0.2956	0.3256	0.030*
C24	0.72808 (10)	−0.16905 (8)	0.34479 (9)	0.01953 (15)
H24	0.7088	−0.2090	0.4290	0.023*
C25	0.70648 (10)	0.39338 (8)	0.48343 (7)	0.01598 (13)
H25A	0.6292	0.4716	0.4719	0.019*
H25B	0.6690	0.3204	0.5594	0.019*
C26	0.84606 (11)	0.43310 (10)	0.49243 (8)	0.01998 (15)
H26A	0.8211	0.4619	0.5587	0.030*
H26B	0.8826	0.5069	0.4183	0.030*
H26C	0.9224	0.3556	0.5059	0.030*

	U11	U22	U33	U12	U13	U23
S1	0.01224 (8)	0.01495 (8)	0.01383 (8)	−0.00040 (6)	−0.00266 (6)	−0.00755 (6)
O1	0.0120 (3)	0.0218 (3)	0.0199 (3)	−0.0020 (2)	−0.0028 (2)	−0.0102 (2)
O2	0.0197 (3)	0.0158 (2)	0.0195 (3)	0.0003 (2)	−0.0050 (2)	−0.0105 (2)
N1	0.0123 (3)	0.0147 (2)	0.0142 (2)	−0.0013 (2)	−0.0032 (2)	−0.0064 (2)
N2	0.0121 (3)	0.0180 (3)	0.0266 (3)	−0.0015 (2)	−0.0028 (3)	−0.0138 (3)
C1	0.0138 (3)	0.0146 (3)	0.0168 (3)	−0.0023 (2)	−0.0026 (3)	−0.0063 (2)
C2	0.0128 (3)	0.0135 (3)	0.0138 (3)	−0.0018 (2)	−0.0026 (2)	−0.0060 (2)
C3	0.0142 (3)	0.0133 (3)	0.0140 (3)	−0.0022 (2)	−0.0030 (2)	−0.0050 (2)
C4	0.0141 (3)	0.0138 (3)	0.0154 (3)	−0.0009 (2)	−0.0041 (2)	−0.0061 (2)
C5	0.0172 (3)	0.0152 (3)	0.0190 (3)	0.0005 (3)	−0.0054 (3)	−0.0083 (2)
C6	0.0166 (4)	0.0190 (3)	0.0225 (4)	0.0021 (3)	−0.0046 (3)	−0.0108 (3)
C7	0.0139 (4)	0.0220 (3)	0.0297 (4)	0.0003 (3)	−0.0032 (3)	−0.0133 (3)
C8	0.0131 (3)	0.0207 (3)	0.0304 (4)	−0.0021 (3)	−0.0032 (3)	−0.0133 (3)
C9	0.0136 (3)	0.0157 (3)	0.0193 (3)	−0.0006 (2)	−0.0036 (3)	−0.0089 (2)
C10	0.0132 (3)	0.0153 (3)	0.0147 (3)	−0.0010 (2)	−0.0032 (2)	−0.0073 (2)
C11	0.0124 (3)	0.0155 (3)	0.0132 (3)	−0.0018 (2)	−0.0021 (2)	−0.0071 (2)
C12	0.0147 (3)	0.0147 (3)	0.0128 (3)	0.0001 (2)	−0.0035 (2)	−0.0064 (2)
C13	0.0179 (4)	0.0175 (3)	0.0155 (3)	−0.0033 (3)	−0.0027 (3)	−0.0066 (2)
C14	0.0184 (4)	0.0224 (3)	0.0160 (3)	−0.0037 (3)	−0.0012 (3)	−0.0058 (3)
C15	0.0201 (4)	0.0206 (3)	0.0146 (3)	0.0033 (3)	−0.0035 (3)	−0.0073 (3)
C16	0.0248 (4)	0.0182 (3)	0.0152 (3)	0.0000 (3)	−0.0048 (3)	−0.0087 (3)
C17	0.0190 (4)	0.0172 (3)	0.0154 (3)	−0.0020 (3)	−0.0046 (3)	−0.0077 (2)
C18	0.0290 (5)	0.0336 (5)	0.0188 (4)	0.0037 (4)	0.0008 (4)	−0.0130 (3)
C19	0.0138 (3)	0.0130 (3)	0.0187 (3)	−0.0014 (2)	−0.0038 (3)	−0.0073 (2)
C20	0.0202 (4)	0.0185 (3)	0.0195 (3)	−0.0021 (3)	−0.0059 (3)	−0.0090 (3)
C21	0.0232 (4)	0.0267 (4)	0.0266 (4)	0.0031 (3)	−0.0108 (3)	−0.0169 (3)
C22	0.0211 (4)	0.0255 (4)	0.0431 (5)	0.0049 (3)	−0.0149 (4)	−0.0237 (4)
C23	0.0187 (4)	0.0187 (3)	0.0428 (5)	−0.0015 (3)	−0.0103 (4)	−0.0153 (4)
C24	0.0167 (4)	0.0151 (3)	0.0266 (4)	−0.0026 (3)	−0.0046 (3)	−0.0078 (3)
C25	0.0151 (3)	0.0199 (3)	0.0153 (3)	−0.0019 (3)	−0.0019 (3)	−0.0101 (3)
C26	0.0190 (4)	0.0267 (4)	0.0198 (3)	−0.0047 (3)	−0.0036 (3)	−0.0136 (3)

S1—O2	1.4346 (6)	C12—C17	1.3930 (11)
S1—O1	1.4363 (7)	C12—C13	1.3955 (12)
S1—N1	1.6406 (7)	C13—C14	1.3890 (12)
S1—C12	1.7613 (8)	C13—H13	0.93
N1—C1	1.4913 (10)	C14—C15	1.3957 (13)
N1—C11	1.5068 (10)	C14—H14	0.93
N2—C9	1.4049 (10)	C15—C16	1.3936 (14)
N2—C10	1.4478 (11)	C15—C18	1.5026 (13)
N2—H1N2	0.874 (15)	C16—C17	1.3907 (12)
C1—C2	1.5188 (11)	C16—H16	0.93
C1—H1A	0.97	C17—H17	0.93
C1—H1B	0.97	C18—H18A	0.96
C2—C10	1.5225 (11)	C18—H18B	0.96
C2—C3	1.5241 (10)	C18—H18C	0.96
C2—H2	0.98	C19—C24	1.3947 (11)
C3—C19	1.5167 (11)	C19—C20	1.3984 (12)
C3—C4	1.5289 (12)	C20—C21	1.3906 (12)
C3—H3	0.98	C20—H20	0.93
C4—C5	1.3979 (11)	C21—C22	1.3921 (15)
C4—C9	1.4100 (11)	C21—H21	0.93
C5—C6	1.3879 (13)	C22—C23	1.3846 (16)
C5—H5	0.93	C22—H22	0.93
C6—C7	1.3937 (13)	C23—C24	1.3967 (13)
C6—H6	0.93	C23—H23	0.93
C7—C8	1.3874 (12)	C24—H24	0.93
C7—H7	0.93	C25—C26	1.5234 (12)
C8—C9	1.4003 (12)	C25—H25A	0.97
C8—H8	0.93	C25—H25B	0.97
C10—C11	1.5410 (11)	C26—H26A	0.96
C10—H10	0.98	C26—H26B	0.96
C11—C25	1.5235 (10)	C26—H26C	0.96
C11—H11	0.98
O2—S1—O1	119.99 (4)	N1—C11—H11	109.5
O2—S1—N1	106.92 (4)	C25—C11—H11	109.5
O1—S1—N1	106.32 (4)	C10—C11—H11	109.5
O2—S1—C12	107.98 (4)	C17—C12—C13	120.56 (7)
O1—S1—C12	108.51 (4)	C17—C12—S1	120.00 (6)
N1—S1—C12	106.36 (4)	C13—C12—S1	119.15 (6)
C1—N1—C11	109.19 (6)	C14—C13—C12	119.34 (8)
C1—N1—S1	116.25 (5)	C14—C13—H13	120.3
C11—N1—S1	117.17 (5)	C12—C13—H13	120.3
C9—N2—C10	116.54 (7)	C13—C14—C15	120.86 (8)
C9—N2—H1N2	113.8 (10)	C13—C14—H14	119.6
C10—N2—H1N2	116.9 (10)	C15—C14—H14	119.6
N1—C1—C2	102.47 (6)	C16—C15—C14	118.90 (8)
N1—C1—H1A	111.3	C16—C15—C18	120.51 (9)
C2—C1—H1A	111.3	C14—C15—C18	120.59 (9)
N1—C1—H1B	111.3	C17—C16—C15	120.98 (8)
C2—C1—H1B	111.3	C17—C16—H16	119.5
H1A—C1—H1B	109.2	C15—C16—H16	119.5
C1—C2—C10	101.01 (6)	C16—C17—C12	119.25 (8)
C1—C2—C3	119.66 (6)	C16—C17—H17	120.4
C10—C2—C3	111.59 (6)	C12—C17—H17	120.4
C1—C2—H2	108.0	C15—C18—H18A	109.5
C10—C2—H2	108.0	C15—C18—H18B	109.5
C3—C2—H2	108.0	H18A—C18—H18B	109.5
C19—C3—C2	111.25 (6)	C15—C18—H18C	109.5
C19—C3—C4	113.39 (6)	H18A—C18—H18C	109.5
C2—C3—C4	107.44 (6)	H18B—C18—H18C	109.5
C19—C3—H3	108.2	C24—C19—C20	118.46 (8)
C2—C3—H3	108.2	C24—C19—C3	120.93 (7)
C4—C3—H3	108.2	C20—C19—C3	120.59 (7)
C5—C4—C9	118.20 (8)	C21—C20—C19	120.91 (8)
C5—C4—C3	120.56 (7)	C21—C20—H20	119.5
C9—C4—C3	121.24 (7)	C19—C20—H20	119.5
C6—C5—C4	122.28 (8)	C20—C21—C22	119.93 (9)
C6—C5—H5	118.9	C20—C21—H21	120.0
C4—C5—H5	118.9	C22—C21—H21	120.0
C5—C6—C7	118.98 (8)	C23—C22—C21	119.88 (8)
C5—C6—H6	120.5	C23—C22—H22	120.1
C7—C6—H6	120.5	C21—C22—H22	120.1
C8—C7—C6	119.98 (9)	C22—C23—C24	120.05 (9)
C8—C7—H7	120.0	C22—C23—H23	120.0
C6—C7—H7	120.0	C24—C23—H23	120.0
C7—C8—C9	121.06 (8)	C19—C24—C23	120.76 (9)
C7—C8—H8	119.5	C19—C24—H24	119.6
C9—C8—H8	119.5	C23—C24—H24	119.6
C8—C9—N2	118.22 (7)	C26—C25—C11	113.64 (7)
C8—C9—C4	119.46 (7)	C26—C25—H25A	108.8
N2—C9—C4	122.27 (8)	C11—C25—H25A	108.8
N2—C10—C2	108.59 (6)	C26—C25—H25B	108.8
N2—C10—C11	114.73 (6)	C11—C25—H25B	108.8
C2—C10—C11	103.44 (6)	H25A—C25—H25B	107.7
N2—C10—H10	109.9	C25—C26—H26A	109.5
C2—C10—H10	109.9	C25—C26—H26B	109.5
C11—C10—H10	109.9	H26A—C26—H26B	109.5
N1—C11—C25	109.71 (6)	C25—C26—H26C	109.5
N1—C11—C10	103.05 (6)	H26A—C26—H26C	109.5
C25—C11—C10	115.45 (6)	H26B—C26—H26C	109.5
O2—S1—N1—C1	−175.61 (6)	S1—N1—C11—C25	100.35 (7)
O1—S1—N1—C1	55.08 (6)	C1—N1—C11—C10	−1.35 (7)
C12—S1—N1—C1	−60.43 (6)	S1—N1—C11—C10	−136.16 (5)
O2—S1—N1—C11	−43.94 (6)	N2—C10—C11—N1	146.21 (6)
O1—S1—N1—C11	−173.24 (5)	C2—C10—C11—N1	28.11 (7)
C12—S1—N1—C11	71.25 (6)	N2—C10—C11—C25	−94.20 (8)
C11—N1—C1—C2	−25.88 (8)	C2—C10—C11—C25	147.70 (7)
S1—N1—C1—C2	109.40 (6)	O2—S1—C12—C17	−157.41 (7)
N1—C1—C2—C10	42.60 (7)	O1—S1—C12—C17	−25.90 (8)
N1—C1—C2—C3	165.43 (6)	N1—S1—C12—C17	88.13 (7)
C1—C2—C3—C19	66.47 (9)	O2—S1—C12—C13	28.75 (8)
C10—C2—C3—C19	−176.03 (6)	O1—S1—C12—C13	160.27 (7)
C1—C2—C3—C4	−168.88 (7)	N1—S1—C12—C13	−85.71 (7)
C10—C2—C3—C4	−51.38 (8)	C17—C12—C13—C14	−2.42 (13)
C19—C3—C4—C5	−34.90 (10)	S1—C12—C13—C14	171.38 (7)
C2—C3—C4—C5	−158.25 (7)	C12—C13—C14—C15	−0.53 (13)
C19—C3—C4—C9	145.35 (7)	C13—C14—C15—C16	3.15 (13)
C2—C3—C4—C9	22.00 (10)	C13—C14—C15—C18	−176.99 (9)
C9—C4—C5—C6	1.08 (12)	C14—C15—C16—C17	−2.88 (13)
C3—C4—C5—C6	−178.67 (7)	C18—C15—C16—C17	177.26 (8)
C4—C5—C6—C7	0.52 (13)	C15—C16—C17—C12	0.00 (13)
C5—C6—C7—C8	−1.07 (14)	C13—C12—C17—C16	2.68 (12)
C6—C7—C8—C9	0.01 (15)	S1—C12—C17—C16	−171.07 (6)
C7—C8—C9—N2	−175.93 (9)	C2—C3—C19—C24	−112.37 (8)
C7—C8—C9—C4	1.62 (14)	C4—C3—C19—C24	126.40 (8)
C10—N2—C9—C8	−165.08 (8)	C2—C3—C19—C20	66.09 (10)
C10—N2—C9—C4	17.45 (12)	C4—C3—C19—C20	−55.15 (10)
C5—C4—C9—C8	−2.12 (12)	C24—C19—C20—C21	0.65 (13)
C3—C4—C9—C8	177.63 (8)	C3—C19—C20—C21	−177.84 (8)
C5—C4—C9—N2	175.32 (8)	C19—C20—C21—C22	−0.05 (14)
C3—C4—C9—N2	−4.93 (12)	C20—C21—C22—C23	−0.27 (14)
C9—N2—C10—C2	−45.97 (9)	C21—C22—C23—C24	−0.02 (14)
C9—N2—C10—C11	−161.12 (7)	C20—C19—C24—C23	−0.94 (13)
C1—C2—C10—N2	−166.38 (6)	C3—C19—C24—C23	177.54 (8)
C3—C2—C10—N2	65.36 (8)	C22—C23—C24—C19	0.64 (14)
C1—C2—C10—C11	−44.09 (7)	N1—C11—C25—C26	−179.71 (7)
C3—C2—C10—C11	−172.34 (6)	C10—C11—C25—C26	64.43 (9)
C1—N1—C11—C25	−124.83 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.93	2.40	3.3215 (13)	171
C23—H23···O2ii	0.93	2.53	3.2821 (13)	138
C2—H2···Cg1	0.98	2.94	3.8269 (9)	151
C7—H7···Cg3i	0.93	2.95	3.7883 (12)	151
C10—H10···Cg2iii	0.98	2.83	3.8072 (9)	178

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C4–C9, C12–C17 and C19–C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.93	2.40	3.3215 (13)	171
C23—H23⋯O2ii	0.93	2.53	3.2821 (13)	138
C2—H2⋯Cg1	0.98	2.94	3.8269 (9)	151
C7—H7⋯Cg3i	0.93	2.95	3.7883 (12)	151
C10—H10⋯Cg2iii	0.98	2.83	3.8072 (9)	178

Symmetry codes: (i) ; (ii) ; (iii) .