N-Cyano-7α-methoxy-carbonyl-6,14-endo-ethenotetra-hydro-northebaine.

IN THE TITLE COMPOUND (SYSTEMATIC NAME: methyl 17-cyano-3,6-dimeth-oxy-4,5α-ep-oxy-6,14-endo-ethenomorphinan-7-carboxyl-ate), C(23)H(24)N(2)O(5), the dihydro-furan ring adopts a twist conformation, while the piperidine ring is in a chair conformation. The benzene-fused cyclo-hexene ring adopts an envelope conformation. An intra-molecular C-H⋯O hydrogen bond is observed. Inter-molecular C-H⋯N and C-H⋯O hydrogen bonds form C(5) chains along the a and b axes, respectively, and together they form a three-dimensional network.

Related literature

For general background, see: Parrish et al.(2004 ▶); Bentley & Hardy (1967 ▶); Marton et al. (1995 ▶); Derrick et al. (2000 ▶); Lenz et al. (1986 ▶); Hoskin & Hanks (1991 ▶); Takemori et al. (1972 ▶); Liu et al. (2005 ▶). For the synthesis, see: Odabaşoğlu et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶); Etter (1990 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C23H24N2O5

M = 408.44

Orthorhombic,

a = 7.1880 (3) Å

b = 11.1380 (4) Å

c = 24.6389 (10) Å

V = 1972.59 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.63 × 0.44 × 0.27 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.953, T max = 0.975

9908 measured reflections

2328 independent reflections

2035 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.089

S = 1.04

2328 reflections

274 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809032450/ci2873sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032450/ci2873Isup2.hkl

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

C23H24N2O5	F(000) = 864
Mr = 408.44	Dx = 1.375 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9908 reflections
a = 7.1880 (3) Å	θ = 1.8–28.0°
b = 11.1380 (4) Å	µ = 0.10 mm−1
c = 24.6389 (10) Å	T = 296 K
V = 1972.59 (13) Å3	Prism, colourless
Z = 4	0.63 × 0.44 × 0.27 mm

Stoe IPDS 2 diffractometer	2328 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2035 reflections with I > 2σ(I)
plane graphite	Rint = 0.021
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.0°
ω–scan rotation method	h = −9→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→13
Tmin = 0.953, Tmax = 0.975	l = −30→20
9908 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0504P)2 + 0.208P] where P = (Fo2 + 2Fc2)/3
2328 reflections	(Δ/σ)max = 0.001
274 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.20 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	0.1582 (3)	0.5657 (2)	0.76990 (11)	0.0558 (6)
C2	0.1229 (3)	0.6871 (2)	0.76212 (13)	0.0651 (8)
H2	0.0430	0.7264	0.7859	0.078*
C3	0.2027 (3)	0.7513 (2)	0.72016 (12)	0.0584 (7)
H3	0.1697	0.8312	0.7148	0.070*
C4	0.3316 (3)	0.6975 (2)	0.68598 (10)	0.0494 (5)
C5	0.3793 (3)	0.5805 (2)	0.69774 (9)	0.0431 (5)
C6	0.2847 (3)	0.5129 (2)	0.73515 (9)	0.0438 (5)
C7	0.0990 (5)	0.5179 (3)	0.86177 (15)	0.0929 (11)
H7A	0.2283	0.5034	0.8690	0.139*
H7B	0.0245	0.4650	0.8836	0.139*
H7C	0.0693	0.5997	0.8705	0.139*
C8	0.3985 (4)	0.7488 (2)	0.63180 (11)	0.0619 (7)
H8A	0.4784	0.8171	0.6391	0.074*
H8B	0.2912	0.7783	0.6120	0.074*
C9	0.5055 (4)	0.6599 (2)	0.59495 (10)	0.0550 (6)
H9	0.4781	0.6798	0.5570	0.066*
C10	0.4513 (3)	0.5280 (2)	0.60475 (9)	0.0445 (5)
C11	0.5026 (3)	0.5014 (2)	0.66483 (8)	0.0405 (4)
C12	0.7122 (3)	0.5215 (2)	0.67525 (9)	0.0492 (5)
H12A	0.7375	0.5101	0.7136	0.059*
H12B	0.7827	0.4618	0.6553	0.059*
C13	0.7765 (4)	0.6444 (3)	0.65865 (10)	0.0615 (7)
H13A	0.7284	0.7040	0.6837	0.074*
H13B	0.9113	0.6482	0.6594	0.074*
C14	0.5448 (4)	0.4336 (2)	0.56775 (9)	0.0530 (6)
H14A	0.4972	0.4407	0.5310	0.064*
H14B	0.6782	0.4466	0.5668	0.064*
C15	0.5020 (3)	0.3077 (2)	0.59042 (9)	0.0464 (5)
H15	0.6147	0.2777	0.6083	0.056*
C16	0.3421 (3)	0.31523 (19)	0.63470 (9)	0.0414 (5)
C17	0.4396 (3)	0.37595 (19)	0.68281 (8)	0.0413 (5)
H17	0.5488	0.3285	0.6932	0.050*
C18	0.1924 (3)	0.3955 (2)	0.61281 (9)	0.0460 (5)
H18	0.0696	0.3701	0.6096	0.055*
C19	0.2453 (3)	0.5040 (2)	0.59850 (9)	0.0476 (5)
H19	0.1625	0.5615	0.5856	0.057*
C20	0.3673 (4)	0.1229 (2)	0.67858 (11)	0.0580 (6)
H20A	0.4882	0.1129	0.6627	0.087*
H20B	0.3058	0.0465	0.6803	0.087*
H20C	0.3802	0.1550	0.7145	0.087*
C21	0.4457 (3)	0.2176 (2)	0.54757 (10)	0.0524 (6)
C22	0.4577 (6)	0.0119 (3)	0.52491 (12)	0.0800 (9)
H22A	0.3286	−0.0057	0.5309	0.120*
H22B	0.5310	−0.0578	0.5331	0.120*
H22C	0.4760	0.0340	0.4876	0.120*
C23	0.8136 (4)	0.7260 (2)	0.56914 (10)	0.0583 (6)
N1	0.7083 (4)	0.6693 (2)	0.60326 (9)	0.0710 (7)
N2	0.9105 (5)	0.7735 (3)	0.53969 (12)	0.1007 (10)
O1	0.0625 (3)	0.4968 (2)	0.80685 (10)	0.0924 (8)
O2	0.3187 (2)	0.39121 (14)	0.73017 (6)	0.0487 (4)
O3	0.2608 (2)	0.20286 (14)	0.64642 (7)	0.0496 (4)
O4	0.3500 (3)	0.2385 (2)	0.50871 (8)	0.0753 (6)
O5	0.5139 (3)	0.10971 (16)	0.55952 (7)	0.0611 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0440 (11)	0.0639 (15)	0.0594 (15)	−0.0158 (11)	0.0118 (11)	−0.0196 (12)
C2	0.0411 (12)	0.0655 (17)	0.089 (2)	−0.0039 (12)	0.0063 (13)	−0.0372 (15)
C3	0.0479 (13)	0.0478 (13)	0.0794 (18)	0.0029 (11)	−0.0166 (13)	−0.0162 (12)
C4	0.0462 (12)	0.0453 (12)	0.0565 (14)	−0.0042 (10)	−0.0137 (11)	−0.0037 (10)
C5	0.0380 (10)	0.0512 (12)	0.0400 (11)	−0.0009 (9)	−0.0052 (9)	−0.0007 (9)
C6	0.0376 (10)	0.0510 (12)	0.0429 (11)	−0.0012 (9)	−0.0001 (9)	−0.0062 (9)
C7	0.076 (2)	0.110 (3)	0.093 (3)	−0.015 (2)	−0.0151 (18)	0.037 (2)
C8	0.0750 (17)	0.0485 (13)	0.0622 (16)	−0.0068 (13)	−0.0176 (14)	0.0088 (12)
C9	0.0606 (15)	0.0632 (15)	0.0413 (12)	−0.0127 (12)	−0.0101 (11)	0.0129 (10)
C10	0.0458 (11)	0.0529 (12)	0.0347 (10)	−0.0025 (10)	−0.0048 (9)	0.0069 (9)
C11	0.0374 (10)	0.0496 (11)	0.0346 (10)	0.0006 (9)	−0.0008 (8)	0.0036 (9)
C12	0.0375 (11)	0.0722 (15)	0.0379 (11)	−0.0018 (10)	−0.0014 (9)	0.0052 (11)
C13	0.0485 (13)	0.0891 (19)	0.0469 (14)	−0.0188 (13)	−0.0052 (11)	0.0121 (12)
C14	0.0539 (13)	0.0704 (15)	0.0348 (11)	−0.0025 (12)	0.0042 (10)	0.0017 (10)
C15	0.0399 (11)	0.0609 (13)	0.0384 (11)	0.0064 (10)	0.0002 (9)	−0.0008 (10)
C16	0.0379 (10)	0.0469 (11)	0.0395 (11)	0.0033 (9)	0.0016 (9)	0.0026 (9)
C17	0.0388 (10)	0.0502 (11)	0.0348 (11)	0.0079 (9)	0.0018 (9)	0.0037 (9)
C18	0.0358 (10)	0.0554 (13)	0.0467 (12)	0.0034 (10)	−0.0052 (9)	−0.0014 (10)
C19	0.0465 (11)	0.0509 (12)	0.0454 (11)	0.0058 (10)	−0.0129 (10)	0.0016 (10)
C20	0.0634 (15)	0.0523 (13)	0.0582 (15)	0.0050 (12)	0.0007 (12)	0.0119 (12)
C21	0.0518 (13)	0.0645 (15)	0.0408 (12)	0.0066 (12)	0.0021 (10)	−0.0039 (11)
C22	0.117 (3)	0.0672 (17)	0.0557 (16)	0.0099 (19)	0.0001 (17)	−0.0166 (14)
C23	0.0749 (16)	0.0556 (14)	0.0443 (13)	−0.0099 (13)	0.0118 (12)	−0.0001 (11)
N1	0.0676 (14)	0.0989 (17)	0.0467 (12)	−0.0295 (13)	−0.0056 (10)	0.0215 (12)
N2	0.101 (2)	0.135 (3)	0.0660 (18)	−0.026 (2)	0.0247 (16)	0.0189 (17)
O1	0.0946 (15)	0.0935 (15)	0.0891 (16)	−0.0483 (13)	0.0573 (13)	−0.0418 (13)
O2	0.0554 (8)	0.0505 (9)	0.0403 (8)	0.0008 (7)	0.0127 (7)	0.0014 (7)
O3	0.0454 (8)	0.0485 (8)	0.0548 (9)	0.0022 (7)	0.0009 (7)	0.0038 (7)
O4	0.0877 (14)	0.0788 (12)	0.0596 (12)	0.0128 (12)	−0.0285 (11)	−0.0099 (9)
O5	0.0748 (11)	0.0627 (10)	0.0459 (9)	0.0161 (10)	−0.0023 (9)	−0.0078 (8)

C1—O1	1.376 (3)	C13—N1	1.476 (3)
C1—C6	1.381 (3)	C13—H13A	0.97
C1—C2	1.389 (4)	C13—H13B	0.97
C2—C3	1.382 (4)	C14—C15	1.541 (3)
C2—H2	0.93	C14—H14A	0.97
C3—C4	1.388 (4)	C14—H14B	0.97
C3—H3	0.93	C15—C21	1.512 (3)
C4—C5	1.379 (3)	C15—C16	1.587 (3)
C4—C8	1.530 (4)	C15—H15	0.98
C5—C6	1.371 (3)	C16—O3	1.411 (3)
C5—C11	1.489 (3)	C16—C18	1.500 (3)
C6—O2	1.383 (3)	C16—C17	1.534 (3)
C7—O1	1.398 (4)	C17—O2	1.465 (2)
C7—H7A	0.96	C17—H17	0.98
C7—H7B	0.96	C18—C19	1.315 (3)
C7—H7C	0.96	C18—H18	0.93
C8—C9	1.548 (4)	C19—H19	0.93
C8—H8A	0.97	C20—O3	1.417 (3)
C8—H8B	0.97	C20—H20A	0.96
C9—N1	1.476 (4)	C20—H20B	0.96
C9—C10	1.539 (3)	C20—H20C	0.96
C9—H9	0.98	C21—O4	1.202 (3)
C10—C19	1.513 (3)	C21—O5	1.330 (3)
C10—C14	1.546 (3)	C22—O5	1.441 (3)
C10—C11	1.554 (3)	C22—H22A	0.96
C11—C17	1.534 (3)	C22—H22B	0.96
C11—C12	1.545 (3)	C22—H22C	0.96
C12—C13	1.502 (4)	C23—N2	1.137 (3)
C12—H12A	0.97	C23—N1	1.296 (3)
C12—H12B	0.97
O1—C1—C6	120.1 (2)	N1—C13—H13B	110.0
O1—C1—C2	122.9 (2)	C12—C13—H13B	110.0
C6—C1—C2	116.7 (2)	H13A—C13—H13B	108.3
C3—C2—C1	122.1 (2)	C15—C14—C10	108.61 (18)
C3—C2—H2	119.0	C15—C14—H14A	110.0
C1—C2—H2	119.0	C10—C14—H14A	110.0
C2—C3—C4	120.5 (2)	C15—C14—H14B	110.0
C2—C3—H3	119.8	C10—C14—H14B	110.0
C4—C3—H3	119.7	H14A—C14—H14B	108.3
C5—C4—C3	116.5 (2)	C21—C15—C14	113.87 (19)
C5—C4—C8	117.3 (2)	C21—C15—C16	108.75 (19)
C3—C4—C8	125.3 (2)	C14—C15—C16	110.19 (18)
C6—C5—C4	122.5 (2)	C21—C15—H15	107.9
C6—C5—C11	109.66 (19)	C14—C15—H15	107.9
C4—C5—C11	126.3 (2)	C16—C15—H15	107.9
C5—C6—C1	120.6 (2)	O3—C16—C18	107.77 (17)
C5—C6—O2	113.00 (18)	O3—C16—C17	114.96 (17)
C1—C6—O2	126.1 (2)	C18—C16—C17	110.04 (17)
O1—C7—H7A	109.5	O3—C16—C15	113.17 (17)
O1—C7—H7B	109.5	C18—C16—C15	107.72 (18)
H7A—C7—H7B	109.5	C17—C16—C15	102.94 (16)
O1—C7—H7C	109.5	O2—C17—C16	113.33 (17)
H7A—C7—H7C	109.5	O2—C17—C11	107.43 (16)
H7B—C7—H7C	109.5	C16—C17—C11	108.24 (16)
C4—C8—C9	115.4 (2)	O2—C17—H17	109.3
C4—C8—H8A	108.4	C16—C17—H17	109.3
C9—C8—H8A	108.4	C11—C17—H17	109.3
C4—C8—H8B	108.4	C19—C18—C16	115.9 (2)
C9—C8—H8B	108.4	C19—C18—H18	122.0
H8A—C8—H8B	107.5	C16—C18—H18	122.0
N1—C9—C10	107.2 (2)	C18—C19—C10	114.7 (2)
N1—C9—C8	111.4 (2)	C18—C19—H19	122.6
C10—C9—C8	113.1 (2)	C10—C19—H19	122.6
N1—C9—H9	108.3	O3—C20—H20A	109.5
C10—C9—H9	108.3	O3—C20—H20B	109.5
C8—C9—H9	108.3	H20A—C20—H20B	109.5
C19—C10—C9	113.6 (2)	O3—C20—H20C	109.5
C19—C10—C14	104.20 (19)	H20A—C20—H20C	109.5
C9—C10—C14	116.56 (19)	H20B—C20—H20C	109.5
C19—C10—C11	107.17 (18)	O4—C21—O5	124.2 (2)
C9—C10—C11	105.77 (18)	O4—C21—C15	125.5 (2)
C14—C10—C11	109.19 (18)	O5—C21—C15	110.3 (2)
C5—C11—C17	101.88 (17)	O5—C22—H22A	109.5
C5—C11—C12	113.82 (19)	O5—C22—H22B	109.5
C17—C11—C12	111.83 (18)	H22A—C22—H22B	109.5
C5—C11—C10	105.35 (18)	O5—C22—H22C	109.5
C17—C11—C10	112.28 (18)	H22A—C22—H22C	109.5
C12—C11—C10	111.22 (18)	H22B—C22—H22C	109.5
C13—C12—C11	112.8 (2)	N2—C23—N1	177.9 (3)
C13—C12—H12A	109.0	C23—N1—C9	121.4 (2)
C11—C12—H12A	109.0	C23—N1—C13	119.8 (2)
C13—C12—H12B	109.0	C9—N1—C13	116.3 (2)
C11—C12—H12B	109.0	C1—O1—C7	116.9 (2)
H12A—C12—H12B	107.8	C6—O2—C17	106.83 (16)
N1—C13—C12	108.7 (2)	C16—O3—C20	116.63 (18)
N1—C13—H13A	110.0	C21—O5—C22	116.6 (2)
C12—C13—H13A	110.0
O1—C1—C2—C3	−171.3 (3)	C10—C14—C15—C16	13.0 (2)
C6—C1—C2—C3	3.1 (4)	C21—C15—C16—O3	38.3 (2)
C1—C2—C3—C4	−4.1 (4)	C14—C15—C16—O3	163.76 (18)
C2—C3—C4—C5	−2.6 (3)	C21—C15—C16—C18	−80.7 (2)
C2—C3—C4—C8	166.4 (2)	C14—C15—C16—C18	44.7 (2)
C3—C4—C5—C6	10.5 (3)	C21—C15—C16—C17	162.99 (18)
C8—C4—C5—C6	−159.4 (2)	C14—C15—C16—C17	−71.5 (2)
C3—C4—C5—C11	175.0 (2)	O3—C16—C17—O2	−55.4 (2)
C8—C4—C5—C11	5.1 (3)	C18—C16—C17—O2	66.5 (2)
C4—C5—C6—C1	−11.9 (3)	C15—C16—C17—O2	−178.91 (16)
C11—C5—C6—C1	−178.7 (2)	O3—C16—C17—C11	−174.44 (16)
C4—C5—C6—O2	162.9 (2)	C18—C16—C17—C11	−52.6 (2)
C11—C5—C6—O2	−3.9 (2)	C15—C16—C17—C11	62.0 (2)
O1—C1—C6—C5	179.3 (2)	C5—C11—C17—O2	−10.9 (2)
C2—C1—C6—C5	4.7 (3)	C12—C11—C17—O2	111.03 (19)
O1—C1—C6—O2	5.2 (4)	C10—C11—C17—O2	−123.14 (18)
C2—C1—C6—O2	−169.4 (2)	C5—C11—C17—C16	111.83 (18)
C5—C4—C8—C9	2.8 (3)	C12—C11—C17—C16	−126.25 (19)
C3—C4—C8—C9	−166.1 (2)	C10—C11—C17—C16	−0.4 (2)
C4—C8—C9—N1	−94.0 (3)	O3—C16—C18—C19	−178.53 (19)
C4—C8—C9—C10	26.8 (3)	C17—C16—C18—C19	55.4 (3)
N1—C9—C10—C19	179.2 (2)	C15—C16—C18—C19	−56.1 (3)
C8—C9—C10—C19	56.0 (3)	C16—C18—C19—C10	2.1 (3)
N1—C9—C10—C14	−59.6 (3)	C9—C10—C19—C18	−172.41 (19)
C8—C9—C10—C14	177.2 (2)	C14—C10—C19—C18	59.7 (3)
N1—C9—C10—C11	61.9 (2)	C11—C10—C19—C18	−56.0 (3)
C8—C9—C10—C11	−61.3 (2)	C14—C15—C21—O4	−38.1 (3)
C6—C5—C11—C17	9.0 (2)	C16—C15—C21—O4	85.2 (3)
C4—C5—C11—C17	−157.1 (2)	C14—C15—C21—O5	143.4 (2)
C6—C5—C11—C12	−111.5 (2)	C16—C15—C21—O5	−93.3 (2)
C4—C5—C11—C12	82.3 (3)	N2—C23—N1—C9	−154 (9)
C6—C5—C11—C10	126.37 (19)	N2—C23—N1—C13	45 (9)
C4—C5—C11—C10	−39.8 (3)	C10—C9—N1—C23	133.5 (3)
C19—C10—C11—C5	−57.1 (2)	C8—C9—N1—C23	−102.3 (3)
C9—C10—C11—C5	64.4 (2)	C10—C9—N1—C13	−64.4 (3)
C14—C10—C11—C5	−169.41 (18)	C8—C9—N1—C13	59.9 (3)
C19—C10—C11—C17	53.0 (2)	C12—C13—N1—C23	−141.3 (3)
C9—C10—C11—C17	174.49 (18)	C12—C13—N1—C9	56.2 (3)
C14—C10—C11—C17	−59.3 (2)	C6—C1—O1—C7	114.6 (3)
C19—C10—C11—C12	179.1 (2)	C2—C1—O1—C7	−71.2 (4)
C9—C10—C11—C12	−59.3 (2)	C5—C6—O2—C17	−3.5 (2)
C14—C10—C11—C12	66.8 (2)	C1—C6—O2—C17	170.9 (2)
C5—C11—C12—C13	−64.4 (3)	C16—C17—O2—C6	−110.32 (19)
C17—C11—C12—C13	−179.20 (18)	C11—C17—O2—C6	9.2 (2)
C10—C11—C12—C13	54.4 (3)	C18—C16—O3—C20	−166.3 (2)
C11—C12—C13—N1	−48.9 (3)	C17—C16—O3—C20	−43.2 (2)
C19—C10—C14—C15	−64.4 (2)	C15—C16—O3—C20	74.7 (2)
C9—C10—C14—C15	169.59 (19)	O4—C21—O5—C22	−4.0 (4)
C11—C10—C14—C15	49.9 (2)	C15—C21—O5—C22	174.5 (2)
C10—C14—C15—C21	135.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···O5	0.96	2.55	3.120 (3)	118
C3—H3···O1i	0.93	2.54	3.399 (3)	153
C9—H9···N2ii	0.98	2.49	3.467 (4)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20A⋯O5	0.96	2.55	3.120 (3)	118
C3—H3⋯O1i	0.93	2.54	3.399 (3)	153
C9—H9⋯N2ii	0.98	2.49	3.467 (4)	179

Symmetry codes: (i) ; (ii) .