3-Ethyl-2,6-bis­(4-methoxy­phen­yl)­piperidin-4-one

Kavitha, T.; Ponnuswamy, S.; Mohanraj, V.; Ilango, S.S.; Ponnuswamy, M.N.

doi:10.1107/S1600536807041475

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3-Ethyl-2,6-bis(4-methoxyphenyl)piperidin-4-one

T. Kavitha, S. Ponnuswamy, V. Mohanraj, S. S. Ilango and M. N. Ponnuswamy

In the title molecule, C₂₁H₂₅NO₃, the piperidine ring is in a chair conformation. The dihedral angle between the two benzene rings is 48.4 (1)°. The methoxy groups are almost coplanar with the attached benzene rings. The molecular and crystal structures are stabilized by C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041475/ci2447sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041475/ci2447Isup2.hkl Contains datablock I

CCDC reference: 663710

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.066
wR factor = 0.220
Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C6     = ...          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Nitrogen heterocycles, in particular piperidone alkaloids, occur in both plants and animals and some of them possess a variety of biological activities, including cytotoxic and anti-cancer properties (Dimmock et al., 1990; Mutus et al., 1989). In view of the above importance, the X-ray crystal structure determination of the title compound has been undertaken.

Bond lengths and angles (Fig. 1) are comparable to those observed for 3-methyl-2,6-diphenyl-4-piperidone (Sekar et al., 1990). The piperidine ring adopts a chair conformation, with a puckering amplitude Q_T of 0.577 (3) Å (Nardelli, 1995). The two benzene rings are in equatorial orientation with respect to the piperidine ring which is evidenced from the torsion angles C15—C6—C5—C4 of 174.7 (3)° and C4—C3—C2—C9 of -178.6 (2)°. The ethyl group substitued at C3 is also oriented equatorially with the N1—C2—C3—C7 torsion angle being 178.4 (2)°. The dihedral angle between the two benzene rings is 48.4 (1)°. The methoxy groups are almost coplanar with the attached benzene rings.

The molecular structure is stabilized by a C—H···π interaction involving the C9—C14 benzene ring (centroid Cg1). The crystal structure is stabilized by C—H···π interactions (Desiraju, 1989) involving the C15—C20 benzene ring (centroid Cg2). The packing of the molecules viewed down the a axis is shown in Fig.2. In addition to the above-mentioned interactions, the structure is also stabilized by van der Waals forces

Related literature top

For related literature, see: Desiraju (1989); Dimmock et al. (1990); Sekar et al. (1990); Mutus et al. (1989).

Experimental top

The condensation reaction involving anisaldehyde (24.3 ml, 200 mmol), ammonium acetate (7.7 g, 100 mmol) and pentan-2-one (10.7 ml, 100 mmol) afforded the title compound. Single crystals of the title compound were obtained by slow evaporation of a benzene-petroleum ether (8:1) solution.

Structure description top

For related literature, see: Desiraju (1989); Dimmock et al. (1990); Sekar et al. (1990); Mutus et al. (1989).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 20% probability level. For the sake of clarity, H atoms have been omitted.
	Fig. 2. Crystal packing viewed down the a axis.

3-Ethyl-2,6-bis(4-methoxyphenyl)piperidin-4-one top

Crystal data top

C₂₁H₂₅NO₃	F(000) = 728
M_r = 339.42	D_x = 1.246 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3270 reflections
a = 14.012 (2) Å	θ = 1.6–25.3°
b = 7.8060 (14) Å	µ = 0.08 mm⁻¹
c = 17.655 (3) Å	T = 293 K
β = 110.401 (5)°	Block, colourless
V = 1810.0 (5) Å³	0.15 × 0.13 × 0.10 mm
Z = 4

Data collection top

Bruker Kappa APEX II area-detector diffractometer	2348 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.060
Graphite monochromator	θ_max = 25.3°, θ_min = 1.6°
ω and φ scans	h = −15→16
15103 measured reflections	k = −9→9
3270 independent reflections	l = −21→21

Refinement top

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.220	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.1169P)² + 0.8076P] where P = (F_o² + 2F_c²)/3
3270 reflections	(Δ/σ)_max = 0.001
230 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₁H₂₅NO₃	V = 1810.0 (5) Å³
M_r = 339.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.012 (2) Å	µ = 0.08 mm⁻¹
b = 7.8060 (14) Å	T = 293 K
c = 17.655 (3) Å	0.15 × 0.13 × 0.10 mm
β = 110.401 (5)°

Data collection top

Bruker Kappa APEX II area-detector diffractometer	2348 reflections with I > 2σ(I)
15103 measured reflections	R_int = 0.060
3270 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.220	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.26 e Å⁻³
3270 reflections	Δρ_min = −0.27 e Å⁻³
230 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
H1	0.465 (2)	0.530 (5)	0.1687 (19)	0.057 (9)*
C2	0.54806 (18)	0.3215 (4)	0.17902 (16)	0.0411 (7)
H2	0.5470	0.2782	0.2308	0.049*
C3	0.54152 (19)	0.1662 (4)	0.12238 (16)	0.0422 (7)
H3	0.5390	0.2119	0.0700	0.051*
C4	0.4410 (2)	0.0763 (4)	0.10928 (18)	0.0462 (7)
C5	0.3484 (2)	0.1890 (4)	0.08452 (18)	0.0492 (7)
H5A	0.2904	0.1234	0.0863	0.059*
H5B	0.3337	0.2270	0.0293	0.059*
C6	0.36336 (19)	0.3454 (4)	0.13980 (17)	0.0418 (7)
H6	0.3705	0.3066	0.1943	0.050*
C7	0.6321 (2)	0.0451 (4)	0.1516 (2)	0.0544 (8)
H7A	0.6594	0.0486	0.2102	0.065*
H7B	0.6082	−0.0706	0.1358	0.065*
C8	0.7175 (3)	0.0832 (5)	0.1204 (2)	0.0678 (10)
H8A	0.7712	0.0011	0.1421	0.102*
H8B	0.7433	0.1963	0.1368	0.102*
H8C	0.6923	0.0763	0.0625	0.102*
C9	0.64449 (19)	0.4237 (4)	0.19468 (16)	0.0400 (6)
C10	0.7234 (2)	0.4118 (4)	0.26803 (16)	0.0427 (7)
H10	0.7151	0.3450	0.3089	0.051*
C11	0.81529 (19)	0.4977 (4)	0.28201 (16)	0.0446 (7)
H11	0.8680	0.4867	0.3314	0.054*
C12	0.8272 (2)	0.5987 (4)	0.22232 (17)	0.0429 (7)
C13	0.7491 (2)	0.6126 (4)	0.14879 (17)	0.0484 (7)
H13	0.7576	0.6795	0.1080	0.058*
C14	0.6584 (2)	0.5277 (4)	0.13550 (17)	0.0472 (7)
H14	0.6057	0.5402	0.0862	0.057*
C15	0.27395 (19)	0.4669 (4)	0.11000 (16)	0.0399 (6)
C16	0.2672 (2)	0.5889 (4)	0.05091 (17)	0.0478 (7)
H16	0.3198	0.5993	0.0306	0.057*
C17	0.1835 (2)	0.6948 (4)	0.02204 (17)	0.0481 (7)
H17	0.1804	0.7759	−0.0173	0.058*
C18	0.10395 (19)	0.6814 (4)	0.05126 (16)	0.0422 (7)
C19	0.10883 (19)	0.5612 (4)	0.10976 (17)	0.0447 (7)
H19	0.0558	0.5508	0.1297	0.054*
C20	0.1939 (2)	0.4555 (4)	0.13862 (17)	0.0438 (7)
H20	0.1970	0.3750	0.1782	0.053*
C21	0.9997 (2)	0.6714 (5)	0.3003 (2)	0.0695 (10)
H21A	1.0539	0.7436	0.2977	0.104*
H21B	1.0213	0.5540	0.3051	0.104*
H21C	0.9822	0.7024	0.3465	0.104*
C22	−0.0592 (2)	0.7846 (5)	0.0444 (2)	0.0583 (9)
H22A	−0.1079	0.8711	0.0175	0.087*
H22B	−0.0376	0.8016	0.1018	0.087*
H22C	−0.0899	0.6735	0.0311	0.087*
N1	0.45796 (16)	0.4296 (3)	0.14268 (15)	0.0451 (6)
O1	0.43561 (17)	−0.0761 (3)	0.12028 (19)	0.0785 (8)
O2	0.91367 (15)	0.6923 (3)	0.22939 (13)	0.0614 (6)
O3	0.02622 (15)	0.7956 (3)	0.01916 (13)	0.0572 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0278 (13)	0.0504 (16)	0.0437 (14)	0.0004 (12)	0.0109 (11)	0.0018 (12)
C3	0.0321 (14)	0.0487 (16)	0.0465 (15)	0.0016 (12)	0.0145 (12)	0.0041 (12)
C4	0.0365 (15)	0.0428 (17)	0.0587 (18)	−0.0027 (12)	0.0160 (13)	−0.0059 (13)
C5	0.0323 (15)	0.0490 (17)	0.0615 (18)	−0.0029 (12)	0.0102 (13)	−0.0046 (14)
C6	0.0290 (13)	0.0486 (16)	0.0475 (15)	0.0016 (11)	0.0129 (11)	−0.0004 (12)
C7	0.0368 (15)	0.0480 (18)	0.080 (2)	0.0054 (13)	0.0223 (15)	0.0078 (15)
C8	0.0468 (18)	0.060 (2)	0.107 (3)	0.0027 (15)	0.0401 (19)	−0.0070 (19)
C9	0.0292 (13)	0.0446 (15)	0.0437 (14)	0.0004 (11)	0.0094 (11)	−0.0019 (12)
C10	0.0336 (14)	0.0506 (16)	0.0433 (15)	−0.0004 (12)	0.0124 (11)	0.0045 (12)
C11	0.0280 (13)	0.0567 (18)	0.0435 (15)	0.0014 (12)	0.0056 (11)	0.0035 (13)
C12	0.0317 (14)	0.0445 (16)	0.0511 (16)	−0.0017 (12)	0.0125 (12)	−0.0010 (13)
C13	0.0435 (16)	0.0490 (17)	0.0496 (16)	−0.0021 (13)	0.0124 (13)	0.0087 (13)
C14	0.0346 (15)	0.0544 (18)	0.0449 (15)	0.0006 (13)	0.0040 (12)	0.0060 (13)
C15	0.0266 (13)	0.0485 (16)	0.0428 (14)	−0.0004 (11)	0.0099 (11)	−0.0020 (12)
C16	0.0325 (14)	0.0616 (19)	0.0550 (17)	−0.0008 (13)	0.0226 (13)	0.0010 (14)
C17	0.0392 (15)	0.0566 (18)	0.0528 (16)	0.0026 (13)	0.0213 (13)	0.0106 (14)
C18	0.0303 (14)	0.0456 (15)	0.0490 (15)	−0.0002 (12)	0.0118 (11)	−0.0025 (12)
C19	0.0274 (13)	0.0550 (17)	0.0561 (17)	−0.0013 (12)	0.0201 (12)	−0.0013 (14)
C20	0.0329 (14)	0.0506 (17)	0.0496 (16)	−0.0029 (12)	0.0165 (12)	0.0033 (13)
C21	0.0327 (16)	0.082 (2)	0.081 (2)	−0.0140 (16)	0.0043 (15)	0.0105 (19)
C22	0.0329 (15)	0.066 (2)	0.076 (2)	0.0050 (14)	0.0195 (14)	−0.0070 (17)
N1	0.0272 (12)	0.0445 (14)	0.0599 (15)	−0.0008 (10)	0.0106 (10)	−0.0070 (12)
O1	0.0477 (14)	0.0490 (15)	0.141 (2)	−0.0038 (11)	0.0357 (14)	−0.0003 (14)
O2	0.0366 (11)	0.0731 (16)	0.0672 (14)	−0.0154 (10)	0.0090 (10)	0.0132 (11)
O3	0.0362 (11)	0.0648 (14)	0.0737 (14)	0.0122 (10)	0.0231 (10)	0.0125 (11)

Geometric parameters (Å, º) top

C2—N1	1.468 (3)	C11—H11	0.93
C2—C9	1.509 (4)	C12—C13	1.380 (4)
C2—C3	1.554 (4)	C12—O2	1.382 (3)
C2—H2	0.98	C13—C14	1.379 (4)
C3—C4	1.517 (4)	C13—H13	0.93
C3—C7	1.521 (4)	C14—H14	0.93
C3—H3	0.98	C15—C20	1.384 (4)
C4—O1	1.212 (4)	C15—C16	1.391 (4)
C4—C5	1.502 (4)	C16—C17	1.379 (4)
C5—C6	1.531 (4)	C16—H16	0.93
C5—H5A	0.97	C17—C18	1.385 (4)
C5—H5B	0.97	C17—H17	0.93
C6—N1	1.464 (3)	C18—O3	1.368 (3)
C6—C15	1.512 (4)	C18—C19	1.379 (4)
C6—H6	0.98	C19—C20	1.392 (4)
C7—C8	1.511 (4)	C19—H19	0.93
C7—H7A	0.97	C20—H20	0.93
C7—H7B	0.97	C21—O2	1.413 (4)
C8—H8A	0.96	C21—H21A	0.96
C8—H8B	0.96	C21—H21B	0.96
C8—H8C	0.96	C21—H21C	0.96
C9—C10	1.382 (4)	C22—O3	1.418 (3)
C9—C14	1.389 (4)	C22—H22A	0.96
C10—C11	1.395 (4)	C22—H22B	0.96
C10—H10	0.93	C22—H22C	0.96
C11—C12	1.372 (4)	N1—H1	0.90 (3)

N1—C2—C9	110.8 (2)	C12—C11—H11	120.3
N1—C2—C3	108.6 (2)	C10—C11—H11	120.3
C9—C2—C3	112.2 (2)	C11—C12—C13	119.9 (3)
N1—C2—H2	108.4	C11—C12—O2	124.9 (2)
C9—C2—H2	108.4	C13—C12—O2	115.2 (2)
C3—C2—H2	108.4	C14—C13—C12	120.3 (3)
C4—C3—C7	112.6 (2)	C14—C13—H13	119.9
C4—C3—C2	107.6 (2)	C12—C13—H13	119.9
C7—C3—C2	114.3 (2)	C13—C14—C9	121.0 (2)
C4—C3—H3	107.3	C13—C14—H14	119.5
C7—C3—H3	107.3	C9—C14—H14	119.5
C2—C3—H3	107.3	C20—C15—C16	117.7 (2)
O1—C4—C5	121.7 (3)	C20—C15—C6	120.7 (2)
O1—C4—C3	122.4 (3)	C16—C15—C6	121.5 (2)
C5—C4—C3	115.8 (2)	C17—C16—C15	121.0 (3)
C4—C5—C6	111.7 (2)	C17—C16—H16	119.5
C4—C5—H5A	109.3	C15—C16—H16	119.5
C6—C5—H5A	109.3	C16—C17—C18	120.5 (3)
C4—C5—H5B	109.3	C16—C17—H17	119.7
C6—C5—H5B	109.3	C18—C17—H17	119.7
H5A—C5—H5B	107.9	O3—C18—C19	125.3 (2)
N1—C6—C15	111.1 (2)	O3—C18—C17	115.1 (3)
N1—C6—C5	107.5 (2)	C19—C18—C17	119.6 (3)
C15—C6—C5	111.4 (2)	C18—C19—C20	119.3 (2)
N1—C6—H6	108.9	C18—C19—H19	120.3
C15—C6—H6	108.9	C20—C19—H19	120.3
C5—C6—H6	108.9	C15—C20—C19	121.9 (3)
C8—C7—C3	115.3 (3)	C15—C20—H20	119.1
C8—C7—H7A	108.5	C19—C20—H20	119.1
C3—C7—H7A	108.5	O2—C21—H21A	109.5
C8—C7—H7B	108.5	O2—C21—H21B	109.5
C3—C7—H7B	108.5	H21A—C21—H21B	109.5
H7A—C7—H7B	107.5	O2—C21—H21C	109.5
C7—C8—H8A	109.5	H21A—C21—H21C	109.5
C7—C8—H8B	109.5	H21B—C21—H21C	109.5
H8A—C8—H8B	109.5	O3—C22—H22A	109.5
C7—C8—H8C	109.5	O3—C22—H22B	109.5
H8A—C8—H8C	109.5	H22A—C22—H22B	109.5
H8B—C8—H8C	109.5	O3—C22—H22C	109.5
C10—C9—C14	117.9 (2)	H22A—C22—H22C	109.5
C10—C9—C2	120.6 (2)	H22B—C22—H22C	109.5
C14—C9—C2	121.5 (2)	C6—N1—C2	112.8 (2)
C9—C10—C11	121.4 (3)	C6—N1—H1	110 (2)
C9—C10—H10	119.3	C2—N1—H1	111 (2)
C11—C10—H10	119.3	C12—O2—C21	117.9 (2)
C12—C11—C10	119.5 (2)	C18—O3—C22	117.9 (2)

N1—C2—C3—C4	−55.8 (3)	C12—C13—C14—C9	−1.5 (5)
C9—C2—C3—C4	−178.6 (2)	C10—C9—C14—C13	1.7 (4)
N1—C2—C3—C7	178.4 (2)	C2—C9—C14—C13	−176.1 (3)
C9—C2—C3—C7	55.5 (3)	N1—C6—C15—C20	−146.8 (3)
C7—C3—C4—O1	−1.0 (4)	C5—C6—C15—C20	93.3 (3)
C2—C3—C4—O1	−127.8 (3)	N1—C6—C15—C16	35.8 (4)
C7—C3—C4—C5	176.9 (3)	C5—C6—C15—C16	−84.1 (3)
C2—C3—C4—C5	50.1 (3)	C20—C15—C16—C17	0.1 (4)
O1—C4—C5—C6	128.2 (3)	C6—C15—C16—C17	177.6 (3)
C3—C4—C5—C6	−49.7 (3)	C15—C16—C17—C18	−0.2 (5)
C4—C5—C6—N1	52.6 (3)	C16—C17—C18—O3	178.7 (3)
C4—C5—C6—C15	174.6 (2)	C16—C17—C18—C19	0.1 (4)
C4—C3—C7—C8	144.8 (3)	O3—C18—C19—C20	−178.4 (3)
C2—C3—C7—C8	−92.0 (3)	C17—C18—C19—C20	0.2 (4)
N1—C2—C9—C10	133.4 (3)	C16—C15—C20—C19	0.2 (4)
C3—C2—C9—C10	−105.0 (3)	C6—C15—C20—C19	−177.3 (2)
N1—C2—C9—C14	−48.8 (4)	C18—C19—C20—C15	−0.3 (4)
C3—C2—C9—C14	72.8 (3)	C15—C6—N1—C2	174.2 (2)
C14—C9—C10—C11	−1.5 (4)	C5—C6—N1—C2	−63.6 (3)
C2—C9—C10—C11	176.3 (3)	C9—C2—N1—C6	−169.6 (2)
C9—C10—C11—C12	1.1 (4)	C3—C2—N1—C6	66.7 (3)
C10—C11—C12—C13	−0.9 (4)	C11—C12—O2—C21	5.9 (5)
C10—C11—C12—O2	178.8 (3)	C13—C12—O2—C21	−174.3 (3)
C11—C12—C13—C14	1.1 (5)	C19—C18—O3—C22	−3.6 (4)
O2—C12—C13—C14	−178.6 (3)	C17—C18—O3—C22	177.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cg1	0.96	2.79	3.662 (4)	152
C10—H10···Cg2ⁱ	0.93	2.87	3.647 (3)	142
C22—H22C···Cg2ⁱⁱ	0.96	2.77	3.637 (4)	151

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₅NO₃
M_r	339.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.012 (2), 7.8060 (14), 17.655 (3)
β (°)	110.401 (5)
V (Å³)	1810.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.15 × 0.13 × 0.10

Data collection
Diffractometer	Bruker Kappa APEX II area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15103, 3270, 2348
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.220, 1.10
No. of reflections	3270
No. of parameters	230
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.27

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 1997) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cg1	0.960	2.79	3.662 (4)	152
C10—H10···Cg2ⁱ	0.930	2.87	3.647 (3)	142
C22—H22C···Cg2ⁱⁱ	0.960	2.77	3.637 (4)	151

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, −y+1, −z.

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