(7R,8S,9S,12S)-1-Benz-yloxy-13,14-didehydro-12-hy-droxy-2,13-dimeth-oxy-N-methyl-morphinane.

In the title compound, C(26)H(31)NO(4), a sinomenine derivative, the angle between the two aromatic rings is 53.34 (4)°. The N-containing ring is in a chair conformation, while the other two non-planar rings are in a half-boat conformation. In the crystal, mol-ecules are linked by O-H⋯N inter-actions into a C(8) chain along [100].

Related literature

For background to the biological effects (such as anti-inflammatory, analgesic, anti-rheumatoid arthritis and arrhythmia, lowering of blood pressure and immune function) of sinomenine derivatives and other related compounds, see: Liu et al. (1994 ▶, 1996 ▶, 1997 ▶); Mark et al. (2003 ▶); Ye et al. (2004 ▶). For related structures, see: Li et al. (2009 ▶); Batterham et al. (1965 ▶); Zheng & Jiang (2010 ▶); Zheng et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For the synthesis of 9S,13R,14S)-7,8-didehydro-4-benz­yloxy-3,7-dimeth­oxy-17-methyl­morphinan-6-one, a starting material in the preparation of the title compound, see: Hitotsuyanagi et al. (1995 ▶).

Experimental

Crystal data

C26H31NO4

M = 421.52

Triclinic,

a = 7.7191 (2) Å

b = 8.5100 (2) Å

c = 9.9630 (2) Å

α = 79.971 (1)°

β = 67.663 (1)°

γ = 64.605 (1)°

V = 546.81 (2) Å3

Z = 1

Cu Kα radiation

μ = 0.69 mm−1

T = 133 K

0.22 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.864, T max = 0.898

9789 measured reflections

2925 independent reflections

2918 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.075

S = 1.07

2925 reflections

320 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1075 Friedel pairs

Flack parameter: −0.09 (14)

Data collection: APEX2 (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037226/bx2370sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037226/bx2370Isup2.hkl

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

C26H31NO4	Z = 1
Mr = 421.52	F(000) = 226
Triclinic, P1	Dx = 1.280 Mg m−3
Hall symbol: P 1	Cu Kα radiation, λ = 1.54178 Å
a = 7.7191 (2) Å	Cell parameters from 9563 reflections
b = 8.5100 (2) Å	θ = 4.8–67.7°
c = 9.9630 (2) Å	µ = 0.69 mm−1
α = 79.971 (1)°	T = 133 K
β = 67.663 (1)°	Block, colourless
γ = 64.605 (1)°	0.22 × 0.18 × 0.16 mm
V = 546.81 (2) Å3

Bruker APEXII CCD diffractometer	2925 independent reflections
Radiation source: fine-focus sealed tube	2918 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 65.0°, θmin = 4.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→8
Tmin = 0.864, Tmax = 0.898	k = −9→10
9789 measured reflections	l = −11→11

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.0495P)2 + 0.074P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2925 reflections	Δρmax = 0.16 e Å−3
320 parameters	Δρmin = −0.21 e Å−3
3 restraints	Absolute structure: Flack (1983), 1075 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.09 (14)

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
N1	−0.1846 (2)	0.69043 (16)	0.42381 (14)	0.0213 (3)
O1	0.20888 (17)	0.54646 (13)	0.78285 (11)	0.0221 (3)
O2	0.1468 (2)	0.84505 (15)	0.88590 (12)	0.0311 (3)
O3	0.6444 (2)	0.43153 (16)	0.48351 (13)	0.0299 (3)
H3	0.699 (5)	0.493 (4)	0.431 (3)	0.048 (7)*
O4	0.7533 (2)	0.42073 (17)	0.17433 (13)	0.0325 (3)
C1	0.1806 (2)	0.6935 (2)	0.69393 (16)	0.0196 (3)
C2	0.1435 (3)	0.8511 (2)	0.74825 (17)	0.0224 (3)
C3	0.0987 (3)	1.0021 (2)	0.66552 (17)	0.0227 (3)
H3A	0.0850	1.1071	0.6974	0.027*
C4	0.0742 (2)	0.99827 (19)	0.53580 (16)	0.0206 (3)
H4	0.0378	1.1031	0.4812	0.025*
C5	0.1011 (2)	0.84563 (19)	0.48291 (15)	0.0178 (3)
C6	0.1651 (2)	0.68794 (19)	0.55900 (16)	0.0180 (3)
C7	0.1781 (2)	0.52104 (19)	0.50805 (15)	0.0186 (3)
C8	0.1850 (2)	0.53675 (19)	0.34957 (15)	0.0191 (3)
H8	0.1607	0.4365	0.3328	0.023*
C9	0.0109 (2)	0.70153 (19)	0.32873 (16)	0.0194 (3)
H9	0.0182	0.7046	0.2260	0.023*
C10	0.0495 (2)	0.85695 (19)	0.34874 (16)	0.0197 (3)
H10A	0.1631	0.8670	0.2625	0.024*
H10B	−0.0738	0.9644	0.3531	0.024*
C11	0.3642 (3)	0.35419 (18)	0.51321 (16)	0.0215 (3)
H11A	0.3646	0.3349	0.6140	0.026*
H11B	0.3489	0.2546	0.4878	0.026*
C12	0.5705 (3)	0.3557 (2)	0.41207 (18)	0.0241 (3)
H12	0.6691	0.2319	0.3919	0.029*
C13	0.5602 (3)	0.4429 (2)	0.26876 (17)	0.0238 (3)
C14	0.3887 (3)	0.5234 (2)	0.23985 (15)	0.0225 (3)
H14	0.3944	0.5747	0.1464	0.027*
C15	−0.0260 (3)	0.50452 (19)	0.60092 (16)	0.0210 (3)
H15A	−0.0259	0.3980	0.5737	0.025*
H15B	−0.0401	0.4940	0.7047	0.025*
C16	−0.2061 (2)	0.6625 (2)	0.57832 (16)	0.0212 (3)
H16A	−0.3340	0.6454	0.6335	0.025*
H16B	−0.2155	0.7670	0.6162	0.025*
C17	0.0786 (4)	1.0089 (3)	0.9494 (2)	0.0391 (5)
H17A	0.172 (4)	1.067 (3)	0.899 (3)	0.042 (6)*
H17B	−0.069 (4)	1.089 (3)	0.950 (2)	0.032 (5)*
H17C	0.082 (4)	0.984 (3)	1.044 (3)	0.043 (6)*
C18	0.7681 (3)	0.4831 (3)	0.0298 (2)	0.0387 (5)
H18A	0.903 (5)	0.467 (3)	−0.018 (3)	0.051 (7)*
H18B	0.692 (4)	0.609 (3)	0.029 (2)	0.042 (6)*
H18C	0.725 (4)	0.419 (3)	−0.020 (3)	0.044 (6)*
C19	−0.3610 (3)	0.8391 (2)	0.4052 (2)	0.0307 (4)
H19A	−0.393 (4)	0.944 (3)	0.456 (2)	0.042 (6)*
H19B	−0.477 (4)	0.811 (3)	0.452 (2)	0.037 (6)*
H19C	−0.340 (4)	0.871 (3)	0.304 (3)	0.038 (6)*
C20	0.3930 (3)	0.4804 (2)	0.81955 (18)	0.0264 (4)
H20A	0.3872	0.5670	0.8776	0.032*
H20B	0.5140	0.4588	0.7299	0.032*
C21	0.4100 (3)	0.3140 (2)	0.90526 (17)	0.0231 (3)
C22	0.2758 (3)	0.3134 (2)	1.04523 (17)	0.0263 (4)
H22	0.1650	0.4186	1.0858	0.032*
C23	0.3022 (3)	0.1601 (2)	1.12647 (17)	0.0335 (4)
H23	0.2098	0.1610	1.2224	0.040*
C24	0.4635 (3)	0.0053 (2)	1.0678 (2)	0.0349 (4)
H24	0.4828	−0.0992	1.1240	0.042*
C25	0.5956 (3)	0.0046 (3)	0.9271 (2)	0.0405 (5)
H25	0.7050	−0.1009	0.8859	0.049*
C26	0.5683 (3)	0.1574 (3)	0.8465 (2)	0.0347 (4)
H26	0.6587	0.1557	0.7497	0.042*

	U11	U22	U33	U12	U13	U23
N1	0.0167 (8)	0.0222 (7)	0.0249 (6)	−0.0089 (6)	−0.0070 (5)	0.0024 (5)
O1	0.0253 (7)	0.0243 (5)	0.0217 (5)	−0.0144 (5)	−0.0113 (5)	0.0073 (4)
O2	0.0463 (9)	0.0300 (6)	0.0225 (6)	−0.0164 (6)	−0.0159 (5)	−0.0007 (5)
O3	0.0305 (7)	0.0379 (7)	0.0307 (6)	−0.0217 (6)	−0.0133 (5)	0.0053 (5)
O4	0.0190 (7)	0.0432 (7)	0.0286 (6)	−0.0103 (6)	−0.0016 (5)	−0.0056 (5)
C1	0.0192 (10)	0.0199 (7)	0.0201 (7)	−0.0102 (7)	−0.0065 (6)	0.0042 (6)
C2	0.0209 (10)	0.0267 (8)	0.0205 (7)	−0.0112 (7)	−0.0058 (6)	−0.0006 (6)
C3	0.0222 (10)	0.0207 (8)	0.0236 (8)	−0.0097 (7)	−0.0036 (7)	−0.0033 (6)
C4	0.0175 (9)	0.0177 (7)	0.0236 (7)	−0.0082 (7)	−0.0039 (6)	0.0023 (6)
C5	0.0125 (8)	0.0195 (7)	0.0173 (7)	−0.0070 (6)	−0.0005 (6)	0.0002 (5)
C6	0.0145 (9)	0.0184 (7)	0.0190 (7)	−0.0079 (6)	−0.0024 (6)	0.0005 (5)
C7	0.0196 (9)	0.0174 (7)	0.0198 (7)	−0.0090 (7)	−0.0068 (6)	0.0023 (5)
C8	0.0180 (9)	0.0189 (7)	0.0209 (7)	−0.0082 (7)	−0.0059 (6)	−0.0010 (5)
C9	0.0186 (9)	0.0222 (7)	0.0168 (6)	−0.0088 (7)	−0.0055 (6)	0.0013 (5)
C10	0.0185 (9)	0.0187 (7)	0.0203 (7)	−0.0077 (7)	−0.0065 (6)	0.0039 (6)
C11	0.0242 (10)	0.0168 (7)	0.0249 (8)	−0.0094 (7)	−0.0096 (7)	0.0021 (6)
C12	0.0190 (9)	0.0185 (7)	0.0327 (8)	−0.0041 (7)	−0.0099 (7)	−0.0018 (6)
C13	0.0183 (10)	0.0225 (7)	0.0271 (8)	−0.0068 (7)	−0.0033 (7)	−0.0062 (6)
C14	0.0233 (10)	0.0224 (7)	0.0192 (7)	−0.0094 (7)	−0.0032 (6)	−0.0030 (6)
C15	0.0238 (9)	0.0204 (7)	0.0223 (7)	−0.0136 (7)	−0.0073 (6)	0.0027 (6)
C16	0.0192 (9)	0.0225 (7)	0.0220 (7)	−0.0109 (7)	−0.0039 (6)	−0.0008 (6)
C17	0.0616 (17)	0.0366 (10)	0.0284 (9)	−0.0220 (11)	−0.0207 (9)	−0.0039 (8)
C18	0.0260 (12)	0.0494 (12)	0.0301 (9)	−0.0144 (10)	0.0006 (8)	−0.0009 (8)
C19	0.0212 (11)	0.0330 (9)	0.0361 (10)	−0.0103 (8)	−0.0114 (8)	0.0063 (8)
C20	0.0265 (10)	0.0319 (9)	0.0279 (8)	−0.0165 (8)	−0.0151 (7)	0.0089 (6)
C21	0.0248 (10)	0.0289 (8)	0.0231 (7)	−0.0154 (7)	−0.0135 (6)	0.0061 (6)
C22	0.0345 (11)	0.0277 (8)	0.0221 (8)	−0.0173 (8)	−0.0092 (7)	−0.0010 (6)
C23	0.0539 (14)	0.0422 (10)	0.0189 (7)	−0.0343 (10)	−0.0126 (8)	0.0060 (7)
C24	0.0414 (13)	0.0320 (9)	0.0415 (10)	−0.0220 (9)	−0.0240 (9)	0.0172 (8)
C25	0.0266 (12)	0.0313 (9)	0.0521 (12)	−0.0054 (8)	−0.0115 (9)	0.0063 (8)
C26	0.0218 (11)	0.0393 (10)	0.0324 (9)	−0.0106 (8)	−0.0032 (7)	0.0069 (7)

N1—C19	1.457 (2)	C11—H11B	0.9900
N1—C16	1.4717 (19)	C12—C13	1.504 (2)
N1—C9	1.479 (2)	C12—H12	1.0000
O1—C1	1.3874 (18)	C13—C14	1.322 (3)
O1—C20	1.452 (2)	C14—H14	0.9500
O2—C2	1.3728 (19)	C15—C16	1.523 (2)
O2—C17	1.431 (2)	C15—H15A	0.9900
O3—C12	1.426 (2)	C15—H15B	0.9900
O3—H3	0.81 (3)	C16—H16A	0.9900
O4—C13	1.377 (2)	C16—H16B	0.9900
O4—C18	1.424 (2)	C17—H17A	0.98 (3)
C1—C6	1.405 (2)	C17—H17B	1.04 (2)
C1—C2	1.407 (2)	C17—H17C	0.94 (3)
C2—C3	1.384 (2)	C18—H18A	0.93 (3)
C3—C4	1.383 (2)	C18—H18B	0.97 (3)
C3—H3A	0.9500	C18—H18C	1.02 (3)
C4—C5	1.390 (2)	C19—H19A	1.00 (2)
C4—H4	0.9500	C19—H19B	0.95 (3)
C5—C6	1.408 (2)	C19—H19C	0.96 (2)
C5—C10	1.511 (2)	C20—C21	1.502 (2)
C6—C7	1.5414 (19)	C20—H20A	0.9900
C7—C11	1.537 (2)	C20—H20B	0.9900
C7—C8	1.5437 (19)	C21—C22	1.386 (2)
C7—C15	1.548 (2)	C21—C26	1.394 (3)
C8—C14	1.505 (2)	C22—C23	1.389 (2)
C8—C9	1.519 (2)	C22—H22	0.9500
C8—H8	1.0000	C23—C24	1.391 (3)
C9—C10	1.534 (2)	C23—H23	0.9500
C9—H9	1.0000	C24—C25	1.384 (3)
C10—H10A	0.9900	C24—H24	0.9500
C10—H10B	0.9900	C25—C26	1.382 (3)
C11—C12	1.531 (2)	C25—H25	0.9500
C11—H11A	0.9900	C26—H26	0.9500
C19—N1—C16	110.48 (13)	C14—C13—O4	126.33 (15)
C19—N1—C9	112.48 (12)	C14—C13—C12	123.58 (15)
C16—N1—C9	113.97 (12)	O4—C13—C12	110.06 (15)
C1—O1—C20	115.41 (11)	C13—C14—C8	122.38 (14)
C2—O2—C17	116.24 (13)	C13—C14—H14	118.8
C12—O3—H3	113.4 (19)	C8—C14—H14	118.8
C13—O4—C18	115.97 (15)	C16—C15—C7	110.79 (12)
O1—C1—C6	119.65 (12)	C16—C15—H15A	109.5
O1—C1—C2	118.96 (12)	C7—C15—H15A	109.5
C6—C1—C2	120.95 (13)	C16—C15—H15B	109.5
O2—C2—C3	123.84 (14)	C7—C15—H15B	109.5
O2—C2—C1	116.36 (13)	H15A—C15—H15B	108.1
C3—C2—C1	119.75 (13)	N1—C16—C15	111.43 (12)
C4—C3—C2	119.21 (13)	N1—C16—H16A	109.3
C4—C3—H3A	120.4	C15—C16—H16A	109.3
C2—C3—H3A	120.4	N1—C16—H16B	109.3
C3—C4—C5	121.95 (13)	C15—C16—H16B	109.3
C3—C4—H4	119.0	H16A—C16—H16B	108.0
C5—C4—H4	119.0	O2—C17—H17A	111.8 (14)
C4—C5—C6	119.53 (13)	O2—C17—H17B	110.5 (12)
C4—C5—C10	118.27 (13)	H17A—C17—H17B	110.3 (19)
C6—C5—C10	122.12 (12)	O2—C17—H17C	106.3 (14)
C1—C6—C5	118.22 (13)	H17A—C17—H17C	107 (2)
C1—C6—C7	121.07 (12)	H17B—C17—H17C	110.8 (19)
C5—C6—C7	119.75 (13)	O4—C18—H18A	105.7 (16)
C11—C7—C6	115.92 (13)	O4—C18—H18B	110.4 (13)
C11—C7—C8	105.00 (12)	H18A—C18—H18B	105 (2)
C6—C7—C8	112.20 (11)	O4—C18—H18C	111.8 (13)
C11—C7—C15	112.20 (12)	H18A—C18—H18C	112 (2)
C6—C7—C15	105.79 (12)	H18B—C18—H18C	112 (2)
C8—C7—C15	105.35 (12)	N1—C19—H19A	112.3 (14)
C14—C8—C9	112.17 (12)	N1—C19—H19B	107.5 (14)
C14—C8—C7	113.37 (12)	H19A—C19—H19B	104.5 (19)
C9—C8—C7	110.21 (12)	N1—C19—H19C	111.7 (14)
C14—C8—H8	106.9	H19A—C19—H19C	107.0 (18)
C9—C8—H8	106.9	H19B—C19—H19C	113.6 (19)
C7—C8—H8	106.9	O1—C20—C21	108.89 (12)
N1—C9—C8	108.56 (11)	O1—C20—H20A	109.9
N1—C9—C10	117.45 (12)	C21—C20—H20A	109.9
C8—C9—C10	107.64 (13)	O1—C20—H20B	109.9
N1—C9—H9	107.6	C21—C20—H20B	109.9
C8—C9—H9	107.6	H20A—C20—H20B	108.3
C10—C9—H9	107.6	C22—C21—C26	118.78 (15)
C5—C10—C9	114.41 (12)	C22—C21—C20	121.23 (16)
C5—C10—H10A	108.7	C26—C21—C20	119.93 (16)
C9—C10—H10A	108.7	C21—C22—C23	120.44 (17)
C5—C10—H10B	108.7	C21—C22—H22	119.8
C9—C10—H10B	108.7	C23—C22—H22	119.8
H10A—C10—H10B	107.6	C22—C23—C24	120.23 (16)
C12—C11—C7	114.76 (12)	C22—C23—H23	119.9
C12—C11—H11A	108.6	C24—C23—H23	119.9
C7—C11—H11A	108.6	C25—C24—C23	119.55 (16)
C12—C11—H11B	108.6	C25—C24—H24	120.2
C7—C11—H11B	108.6	C23—C24—H24	120.2
H11A—C11—H11B	107.6	C26—C25—C24	119.99 (19)
O3—C12—C13	112.56 (13)	C26—C25—H25	120.0
O3—C12—C11	109.93 (13)	C24—C25—H25	120.0
C13—C12—C11	111.95 (14)	C25—C26—C21	120.97 (17)
O3—C12—H12	107.4	C25—C26—H26	119.5
C13—C12—H12	107.4	C21—C26—H26	119.5
C11—C12—H12	107.4
C20—O1—C1—C6	120.66 (16)	C14—C8—C9—C10	−61.20 (15)
C20—O1—C1—C2	−66.93 (18)	C7—C8—C9—C10	66.14 (15)
C17—O2—C2—C3	6.7 (3)	C4—C5—C10—C9	−159.57 (14)
C17—O2—C2—C1	−170.72 (17)	C6—C5—C10—C9	17.2 (2)
O1—C1—C2—O2	2.7 (2)	N1—C9—C10—C5	74.44 (17)
C6—C1—C2—O2	175.01 (16)	C8—C9—C10—C5	−48.35 (16)
O1—C1—C2—C3	−174.81 (16)	C6—C7—C11—C12	−63.95 (17)
C6—C1—C2—C3	−2.5 (2)	C8—C7—C11—C12	60.46 (16)
O2—C2—C3—C4	−171.90 (16)	C15—C7—C11—C12	174.37 (12)
C1—C2—C3—C4	5.4 (2)	C7—C11—C12—O3	87.15 (16)
C2—C3—C4—C5	−2.6 (2)	C7—C11—C12—C13	−38.74 (17)
C3—C4—C5—C6	−3.2 (2)	C18—O4—C13—C14	−3.6 (2)
C3—C4—C5—C10	173.62 (15)	C18—O4—C13—C12	174.42 (14)
O1—C1—C6—C5	169.01 (14)	O3—C12—C13—C14	−118.18 (17)
C2—C1—C6—C5	−3.2 (2)	C11—C12—C13—C14	6.3 (2)
O1—C1—C6—C7	0.3 (2)	O3—C12—C13—O4	63.72 (17)
C2—C1—C6—C7	−171.99 (15)	C11—C12—C13—O4	−171.84 (12)
C4—C5—C6—C1	6.0 (2)	O4—C13—C14—C8	178.32 (14)
C10—C5—C6—C1	−170.68 (14)	C12—C13—C14—C8	0.5 (2)
C4—C5—C6—C7	174.93 (13)	C9—C8—C14—C13	149.84 (14)
C10—C5—C6—C7	−1.8 (2)	C7—C8—C14—C13	24.21 (19)
C1—C6—C7—C11	−52.12 (19)	C11—C7—C15—C16	−172.80 (12)
C5—C6—C7—C11	139.31 (14)	C6—C7—C15—C16	59.89 (15)
C1—C6—C7—C8	−172.72 (14)	C8—C7—C15—C16	−59.11 (14)
C5—C6—C7—C8	18.7 (2)	C19—N1—C16—C15	178.44 (13)
C1—C6—C7—C15	72.91 (18)	C9—N1—C16—C15	−53.76 (16)
C5—C6—C7—C15	−95.66 (15)	C7—C15—C16—N1	55.26 (16)
C11—C7—C8—C14	−51.48 (15)	C1—O1—C20—C21	−175.36 (14)
C6—C7—C8—C14	75.26 (16)	O1—C20—C21—C22	−69.19 (19)
C15—C7—C8—C14	−170.11 (12)	O1—C20—C21—C26	113.59 (17)
C11—C7—C8—C9	−178.15 (12)	C26—C21—C22—C23	1.7 (3)
C6—C7—C8—C9	−51.41 (17)	C20—C21—C22—C23	−175.59 (15)
C15—C7—C8—C9	63.22 (14)	C21—C22—C23—C24	−0.2 (3)
C19—N1—C9—C8	−176.79 (13)	C22—C23—C24—C25	−1.0 (3)
C16—N1—C9—C8	56.45 (15)	C23—C24—C25—C26	0.8 (3)
C19—N1—C9—C10	60.90 (18)	C24—C25—C26—C21	0.6 (3)
C16—N1—C9—C10	−65.86 (16)	C22—C21—C26—C25	−1.9 (3)
C14—C8—C9—N1	170.71 (11)	C20—C21—C26—C25	175.41 (18)
C7—C8—C9—N1	−61.96 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1i	0.81 (3)	2.20 (3)	2.8966 (17)	145 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1i	0.81 (3)	2.20 (3)	2.8966 (17)	145 (2)

Symmetry code: (i) .