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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2817.
Published online 2010 October 20. doi:  10.1107/S1600536810040286
PMCID: PMC3009244

(9S,13R,14S)-7,8-Didehydro-4-(4-iodo­benz­yloxy)-3,7-dimeth­oxy-17-methyl­morphinan-6-one monohydrate

Abstract

In the title compound, C26H28INO4·H2O, benzene rings are inclined at a dihedral angle of 69.9 (1)°. The N-containing ring exhibits a chair conformation, while the other rings approximate to envelope conformations. In the crystal, the uncoordinated water mol­ecule forms inter­molecular O—H(...)O and O—H(...)N hydrogen bonds.

Related literature

For the biological activity of sinomenine derivatives and other related compounds, see: Liu et al. (1994 [triangle], 1996 [triangle], 1997 [triangle]); Mark et al. (2003 [triangle]); Ye et al. (2004 [triangle]). For the synthesis of the title compound, see: Mitsunobu (1981 [triangle]). For related structures, see: Li et al. (2009 [triangle]); Batterham et al. (1965 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2817-scheme1.jpg

Experimental

Crystal data

  • C26H28INO4·H2O
  • M r = 563.41
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2817-efi1.jpg
  • a = 8.9005 (8) Å
  • b = 14.9221 (14) Å
  • c = 9.2426 (9) Å
  • β = 91.432 (2)°
  • V = 1227.2 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.34 mm−1
  • T = 293 K
  • 0.31 × 0.30 × 0.23 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.482, T max = 1.000
  • 7231 measured reflections
  • 5047 independent reflections
  • 4844 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.087
  • S = 1.07
  • 5047 reflections
  • 309 parameters
  • 4 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.98 e Å−3
  • Δρmin = −0.49 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2311 Friedel pairs
  • Flack parameter: −0.016 (17)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040286/bh2309sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040286/bh2309Isup2.hkl

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

Acknowledgments

The project was supported by the National Natural Science Foundation of China (No. 20976017) and the Scientific Research Fund of Hunan Provincial Science and Technology Department of China (No. 2009 C K3070).

supplementary crystallographic information

Comment

We synthesized a new sinomenine derivative (9S,13R,14S)-7,8-didehydro-4-(4'-iodiobenzyloxy)-3,7-dimethoxy-17-methyl-morphinan-6-one monohydrate. Herein, its crystal structure is reported. Biological effects of sinomenine derivatives and related compounds have been described (Liu et al., 1994, 1996, 1997; Mark et al., 2003; Ye et al., 2004).

The molecular structure of (I) is shown in Fig. 1. The crystal structure is stabilized by O—H···O and O—H···N hydrogen bonds linking sinomenine derivative and the water molecule, and weak C—H···O hydrogen bonds between molecules (Fig. 2). Significant aromatic stacking interactions were not found. There exist two planes in the molecule of the title compound: atoms C1/C2/C3/C4/C12/C11 form the benzene plane (I), and atoms C19···C24 form the benzene plane substituted by Iodine (II). The angle between the two planes is 69.9 (1)°. Rings C [C5/C6/C7/C8/C14/C13] and B [C9···C14] in the molecule approximate both an envelope conformation. In contrast, ring D [C9/N1/C16/C15/C13/C14] exhibits an almost regular chair conformation. Similar features have been described in related compounds (Li et al., 2009; Batterham et al., 1965).

Experimental

The title compound was obtained according to the method of Mitsunobu (1981). Light yellow blocks of (I) were grown from a dichloromethane solution.

Refinement

The water H atoms (H5C and H5D) were located in a difference map, and refined freely, although the geometry was restrained to O—H = 0.83 (3) Å and H5C···H5D separation to 1.45 (2) Å. Other H atoms were positioned geometrically, with C—H = 0.93 (aromatic CH), 0.96 (methyl CH3), 0.97 (methylene CH2) or 0.98 Å (methine CH), and were constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(carrier C) or Uiso(H) = 1.5Ueq(carrier C). 2311 Friedel pairs were used for the Flack parameter refinement.

Figures

Fig. 1.
The molecular structure of (I) showing 50% probability displacement ellipsoids.
Fig. 2.
Packing structure of the title compound.

Crystal data

C26H28INO4·H2OF(000) = 572
Mr = 563.41Dx = 1.525 Mg m3
Monoclinic, P21Melting point: 412 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 8.9005 (8) ÅCell parameters from 4522 reflections
b = 14.9221 (14) Åθ = 4.6–56.4°
c = 9.2426 (9) ŵ = 1.34 mm1
β = 91.432 (2)°T = 293 K
V = 1227.2 (2) Å3Prismatic, colourless
Z = 20.31 × 0.30 × 0.23 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer5047 independent reflections
Radiation source: fine-focus sealed tube4844 reflections with I > 2σ(I)
graphiteRint = 0.038
[var phi] and ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000h = −6→11
Tmin = 0.482, Tmax = 1.000k = −18→19
7231 measured reflectionsl = −11→11

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087w = 1/[σ2(Fo2) + (0.0485P)2 + 0.0909P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.004
5047 reflectionsΔρmax = 0.98 e Å3
309 parametersΔρmin = −0.49 e Å3
4 restraintsAbsolute structure: Flack (1983), 2311 Friedel pairs
0 constraintsFlack parameter: −0.016 (17)
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/Ueq
I11.01684 (3)1.24508 (2)0.40697 (3)0.05793 (10)
N10.7186 (4)0.5021 (2)0.1708 (4)0.0481 (8)
O10.3354 (3)0.90402 (19)0.2691 (3)0.0528 (7)
O20.6158 (3)0.86212 (17)0.2123 (2)0.0381 (5)
O30.7304 (3)0.86778 (19)−0.1786 (3)0.0532 (7)
O40.5676 (3)0.7548 (3)−0.3349 (3)0.0504 (7)
O50.9701 (6)0.9909 (3)0.9213 (6)0.0898 (14)
C10.2856 (4)0.6717 (3)0.1460 (5)0.0474 (9)
H10.21040.62900.13300.057*
C20.2469 (4)0.7561 (4)0.1937 (4)0.0497 (10)
H20.14690.77050.20920.060*
C30.3580 (4)0.8183 (3)0.2179 (4)0.0412 (8)
C40.5086 (4)0.7971 (2)0.1890 (4)0.0342 (7)
C50.7896 (4)0.7650 (2)0.0106 (4)0.0386 (8)
H5A0.79680.81640.07450.046*
H5B0.89100.7451−0.00820.046*
C60.7159 (4)0.7938 (2)−0.1298 (4)0.0392 (8)
C70.6302 (4)0.7238 (2)−0.2098 (4)0.0381 (8)
C80.6280 (4)0.6389 (2)−0.1618 (4)0.0407 (8)
H80.57900.5955−0.21780.049*
C90.6273 (4)0.5306 (2)0.0456 (4)0.0422 (8)
H100.62900.4820−0.02560.051*
C100.4626 (4)0.5535 (3)0.0708 (4)0.0471 (9)
H11A0.40550.5417−0.01790.056*
H11B0.42540.51330.14430.056*
C110.4318 (4)0.6484 (3)0.1170 (4)0.0382 (7)
C120.5457 (4)0.7138 (2)0.1318 (4)0.0314 (7)
C130.7065 (4)0.6896 (2)0.0881 (4)0.0348 (7)
C140.7012 (4)0.6117 (2)−0.0221 (4)0.0364 (7)
H90.80530.5952−0.04220.044*
C150.7966 (4)0.6576 (3)0.2203 (4)0.0442 (8)
H15A0.89990.64730.19370.053*
H15B0.79670.70410.29380.053*
C160.7328 (5)0.5722 (3)0.2826 (4)0.0494 (9)
H16A0.79820.55110.36100.059*
H16B0.63490.58440.32180.059*
C170.6656 (6)0.4173 (4)0.2330 (6)0.0710 (14)
H17A0.56840.42620.27340.107*
H17B0.73520.39790.30770.107*
H17C0.65880.37250.15860.107*
C180.6493 (5)0.8804 (3)0.3618 (4)0.0435 (8)
H18A0.70190.82990.40570.052*
H18B0.55710.89000.41320.052*
C190.7461 (4)0.9628 (2)0.3707 (4)0.0369 (7)
C200.7795 (5)0.9999 (3)0.5060 (4)0.0464 (9)
H200.74780.97130.58920.056*
C210.8598 (5)1.0793 (3)0.5171 (4)0.0479 (9)
H210.88081.10450.60740.057*
C220.9082 (4)1.1204 (3)0.3940 (4)0.0410 (8)
C230.8819 (4)1.0833 (3)0.2597 (4)0.0443 (9)
H230.91721.11100.17710.053*
C240.8021 (4)1.0042 (3)0.2494 (4)0.0398 (8)
H240.78550.97810.15900.048*
C250.4769 (6)0.6931 (5)−0.4172 (5)0.0738 (16)
H25A0.53930.6463−0.45390.111*
H25B0.42850.7241−0.49660.111*
H25C0.40220.6677−0.35640.111*
C260.1839 (6)0.9304 (4)0.2891 (7)0.0756 (16)
H26A0.12390.91350.20580.113*
H26B0.17940.99420.30160.113*
H26C0.14610.90140.37350.113*
H5C0.913 (6)0.954 (4)0.879 (7)0.10 (2)*
H5D1.060 (5)0.976 (7)0.937 (14)0.11 (2)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
I10.05580 (15)0.06209 (16)0.05586 (15)−0.02060 (14)0.00072 (10)−0.00469 (15)
N10.0504 (19)0.0413 (17)0.0528 (19)0.0021 (14)0.0037 (15)0.0087 (14)
O10.0508 (16)0.0474 (16)0.0610 (17)0.0130 (12)0.0148 (13)0.0009 (13)
O20.0438 (14)0.0384 (13)0.0321 (11)−0.0044 (10)0.0006 (10)−0.0043 (10)
O30.0535 (17)0.0367 (15)0.0698 (18)−0.0028 (12)0.0062 (14)0.0022 (13)
O40.0530 (14)0.0547 (19)0.0433 (12)−0.0036 (16)−0.0010 (10)0.0055 (15)
O50.072 (3)0.088 (3)0.111 (3)−0.028 (2)0.029 (2)−0.041 (3)
C10.0345 (18)0.057 (3)0.051 (2)−0.0086 (17)0.0049 (17)0.0091 (18)
C20.0323 (15)0.061 (3)0.056 (2)0.0032 (19)0.0095 (14)0.003 (2)
C30.0401 (19)0.047 (2)0.0368 (18)0.0065 (16)0.0071 (15)0.0082 (15)
C40.0339 (18)0.0390 (19)0.0299 (17)−0.0021 (14)0.0027 (14)0.0023 (14)
C50.0313 (15)0.039 (2)0.0459 (17)−0.0061 (13)0.0084 (13)−0.0071 (13)
C60.0322 (17)0.0351 (19)0.051 (2)−0.0019 (14)0.0151 (15)−0.0063 (15)
C70.0383 (16)0.042 (2)0.0345 (16)−0.0025 (13)0.0064 (13)−0.0022 (13)
C80.046 (2)0.0396 (19)0.0372 (18)−0.0082 (16)0.0044 (15)−0.0095 (15)
C90.049 (2)0.039 (2)0.0388 (18)−0.0050 (16)0.0037 (16)−0.0026 (14)
C100.049 (2)0.042 (2)0.050 (2)−0.0103 (16)−0.0032 (17)0.0006 (16)
C110.0362 (17)0.0435 (19)0.0349 (17)−0.0070 (15)−0.0007 (13)0.0034 (14)
C120.0296 (16)0.0366 (18)0.0279 (16)−0.0020 (12)−0.0014 (13)0.0027 (12)
C130.0327 (16)0.0387 (18)0.0330 (16)−0.0015 (13)0.0019 (13)−0.0044 (14)
C140.0392 (19)0.0327 (18)0.0376 (17)−0.0018 (14)0.0065 (14)−0.0045 (13)
C150.0372 (18)0.052 (2)0.044 (2)0.0054 (16)−0.0039 (15)−0.0057 (16)
C160.047 (2)0.059 (3)0.042 (2)0.0088 (18)−0.0034 (17)0.0075 (18)
C170.080 (4)0.054 (3)0.079 (3)−0.002 (2)0.002 (3)0.024 (2)
C180.054 (2)0.040 (2)0.0365 (18)0.0025 (17)−0.0015 (16)0.0011 (14)
C190.0350 (17)0.0387 (18)0.0369 (18)0.0058 (14)−0.0029 (14)0.0005 (14)
C200.055 (2)0.051 (2)0.0335 (18)−0.0047 (18)0.0038 (16)0.0015 (16)
C210.050 (2)0.064 (3)0.0301 (17)−0.0084 (18)0.0003 (15)−0.0069 (16)
C220.0321 (17)0.048 (2)0.0431 (19)−0.0019 (15)0.0014 (14)−0.0044 (15)
C230.0392 (19)0.060 (2)0.0335 (18)−0.0021 (17)0.0041 (14)0.0028 (16)
C240.0414 (19)0.049 (2)0.0295 (16)0.0028 (16)−0.0013 (14)−0.0054 (14)
C250.084 (4)0.092 (4)0.044 (3)−0.024 (3)−0.017 (3)0.009 (2)
C260.063 (3)0.065 (3)0.100 (4)0.023 (2)0.036 (3)0.007 (3)

Geometric parameters (Å, °)

I1—C222.099 (4)C10—H11B0.9700
N1—C91.461 (5)C11—C121.411 (5)
N1—C171.472 (6)C12—C131.541 (5)
N1—C161.474 (6)C13—C151.521 (5)
O1—C31.380 (5)C13—C141.546 (4)
O1—C261.421 (5)C14—H90.9800
O2—C41.374 (4)C15—C161.516 (6)
O2—C181.432 (4)C15—H15A0.9700
O3—C61.201 (5)C15—H15B0.9700
O4—C71.353 (4)C16—H16A0.9700
O4—C251.430 (6)C16—H16B0.9700
O5—H5C0.84 (3)C17—H17A0.9600
O5—H5D0.84 (3)C17—H17B0.9600
C1—C111.380 (5)C17—H17C0.9600
C1—C21.381 (7)C18—C191.502 (5)
C1—H10.9300C18—H18A0.9700
C2—C31.370 (6)C18—H18B0.9700
C2—H20.9300C19—C241.384 (5)
C3—C41.410 (5)C19—C201.393 (5)
C4—C121.392 (5)C20—C211.387 (6)
C5—C61.501 (5)C20—H200.9300
C5—C131.534 (5)C21—C221.371 (5)
C5—H5A0.9700C21—H210.9300
C5—H5B0.9700C22—C231.375 (5)
C6—C71.480 (5)C23—C241.379 (6)
C7—C81.343 (5)C23—H230.9300
C8—C141.488 (5)C24—H240.9300
C8—H80.9300C25—H25A0.9600
C9—C141.520 (5)C25—H25B0.9600
C9—C101.528 (5)C25—H25C0.9600
C9—H100.9800C26—H26A0.9600
C10—C111.507 (6)C26—H26B0.9600
C10—H11A0.9700C26—H26C0.9600
C9—N1—C17112.5 (4)C8—C14—C13111.8 (3)
C9—N1—C16112.6 (3)C9—C14—C13109.5 (3)
C17—N1—C16111.0 (4)C8—C14—H9107.4
C3—O1—C26116.6 (4)C9—C14—H9107.4
C4—O2—C18114.4 (3)C13—C14—H9107.4
C7—O4—C25116.7 (4)C16—C15—C13111.9 (3)
H5C—O5—H5D118 (5)C16—C15—H15A109.2
C11—C1—C2122.4 (4)C13—C15—H15A109.2
C11—C1—H1118.8C16—C15—H15B109.2
C2—C1—H1118.8C13—C15—H15B109.2
C3—C2—C1119.0 (3)H15A—C15—H15B107.9
C3—C2—H2120.5N1—C16—C15110.9 (3)
C1—C2—H2120.5N1—C16—H16A109.4
C2—C3—O1124.9 (4)C15—C16—H16A109.4
C2—C3—C4120.2 (4)N1—C16—H16B109.4
O1—C3—C4114.9 (4)C15—C16—H16B109.4
O2—C4—C12121.3 (3)H16A—C16—H16B108.0
O2—C4—C3118.1 (3)N1—C17—H17A109.5
C12—C4—C3120.5 (4)N1—C17—H17B109.5
C6—C5—C13114.1 (3)H17A—C17—H17B109.5
C6—C5—H5A108.7N1—C17—H17C109.5
C13—C5—H5A108.7H17A—C17—H17C109.5
C6—C5—H5B108.7H17B—C17—H17C109.5
C13—C5—H5B108.7O2—C18—C19108.3 (3)
H5A—C5—H5B107.6O2—C18—H18A110.0
O3—C6—C7121.3 (4)C19—C18—H18A110.0
O3—C6—C5122.6 (3)O2—C18—H18B110.0
C7—C6—C5116.0 (3)C19—C18—H18B110.0
C8—C7—O4126.6 (3)H18A—C18—H18B108.4
C8—C7—C6120.8 (3)C24—C19—C20118.5 (4)
O4—C7—C6112.5 (3)C24—C19—C18122.6 (3)
C7—C8—C14122.3 (3)C20—C19—C18119.0 (3)
C7—C8—H8118.8C21—C20—C19120.3 (4)
C14—C8—H8118.8C21—C20—H20119.8
N1—C9—C14108.7 (3)C19—C20—H20119.8
N1—C9—C10117.5 (3)C22—C21—C20119.5 (4)
C14—C9—C10108.2 (3)C22—C21—H21120.2
N1—C9—H10107.4C20—C21—H21120.2
C14—C9—H10107.4C21—C22—C23121.3 (4)
C10—C9—H10107.4C21—C22—I1120.2 (3)
C11—C10—C9115.8 (3)C23—C22—I1118.5 (3)
C11—C10—H11A108.3C22—C23—C24118.9 (3)
C9—C10—H11A108.3C22—C23—H23120.6
C11—C10—H11B108.3C24—C23—H23120.6
C9—C10—H11B108.3C23—C24—C19121.5 (3)
H11A—C10—H11B107.4C23—C24—H24119.3
C1—C11—C12119.0 (4)C19—C24—H24119.3
C1—C11—C10118.1 (3)O4—C25—H25A109.5
C12—C11—C10122.9 (3)O4—C25—H25B109.5
C4—C12—C11118.5 (3)H25A—C25—H25B109.5
C4—C12—C13122.6 (3)O4—C25—H25C109.5
C11—C12—C13118.8 (3)H25A—C25—H25C109.5
C15—C13—C5110.8 (3)H25B—C25—H25C109.5
C15—C13—C12109.7 (3)O1—C26—H26A109.5
C5—C13—C12114.3 (3)O1—C26—H26B109.5
C15—C13—C14107.5 (3)H26A—C26—H26B109.5
C5—C13—C14104.5 (3)O1—C26—H26C109.5
C12—C13—C14109.6 (3)H26A—C26—H26C109.5
C8—C14—C9112.9 (3)H26B—C26—H26C109.5
C11—C1—C2—C3−2.2 (6)C6—C5—C13—C12−61.4 (4)
C1—C2—C3—O1−178.2 (3)C6—C5—C13—C1458.5 (4)
C1—C2—C3—C42.4 (6)C4—C12—C13—C1584.0 (4)
C26—O1—C3—C2−4.1 (6)C11—C12—C13—C15−94.3 (4)
C26—O1—C3—C4175.4 (4)C4—C12—C13—C5−41.1 (4)
C18—O2—C4—C12−110.7 (3)C11—C12—C13—C5140.6 (3)
C18—O2—C4—C372.3 (4)C4—C12—C13—C14−158.1 (3)
C2—C3—C4—O2178.8 (3)C11—C12—C13—C1423.6 (4)
O1—C3—C4—O2−0.7 (5)C7—C8—C14—C9152.3 (3)
C2—C3—C4—C121.9 (5)C7—C8—C14—C1328.2 (5)
O1—C3—C4—C12−177.6 (3)N1—C9—C14—C8172.5 (3)
C13—C5—C6—O3153.4 (3)C10—C9—C14—C8−59.0 (4)
C13—C5—C6—C7−29.9 (4)N1—C9—C14—C13−62.2 (4)
C25—O4—C7—C86.9 (6)C10—C9—C14—C1366.4 (4)
C25—O4—C7—C6−177.4 (4)C15—C13—C14—C8−174.5 (3)
O3—C6—C7—C8172.9 (4)C5—C13—C14—C8−56.7 (4)
C5—C6—C7—C8−3.9 (5)C12—C13—C14—C866.3 (4)
O3—C6—C7—O4−3.1 (5)C15—C13—C14—C959.6 (4)
C5—C6—C7—O4−179.9 (3)C5—C13—C14—C9177.3 (3)
O4—C7—C8—C14179.8 (3)C12—C13—C14—C9−59.7 (4)
C6—C7—C8—C144.4 (5)C5—C13—C15—C16−169.2 (3)
C17—N1—C9—C14−173.1 (4)C12—C13—C15—C1663.7 (4)
C16—N1—C9—C1460.6 (4)C14—C13—C15—C16−55.5 (4)
C17—N1—C9—C1063.8 (5)C9—N1—C16—C15−56.4 (4)
C16—N1—C9—C10−62.6 (4)C17—N1—C16—C15176.4 (4)
N1—C9—C10—C1186.5 (4)C13—C15—C16—N154.0 (4)
C14—C9—C10—C11−36.9 (4)C4—O2—C18—C19−170.1 (3)
C2—C1—C11—C12−2.1 (6)O2—C18—C19—C24−6.3 (5)
C2—C1—C11—C10177.7 (4)O2—C18—C19—C20172.8 (3)
C9—C10—C11—C1−177.8 (3)C24—C19—C20—C213.6 (6)
C9—C10—C11—C122.0 (5)C18—C19—C20—C21−175.6 (4)
O2—C4—C12—C11177.0 (3)C19—C20—C21—C22−1.0 (6)
C3—C4—C12—C11−6.2 (5)C20—C21—C22—C23−1.6 (6)
O2—C4—C12—C13−1.3 (5)C20—C21—C22—I1175.7 (3)
C3—C4—C12—C13175.5 (3)C21—C22—C23—C241.5 (6)
C1—C11—C12—C46.3 (5)I1—C22—C23—C24−175.9 (3)
C10—C11—C12—C4−173.6 (3)C22—C23—C24—C191.2 (6)
C1—C11—C12—C13−175.4 (3)C20—C19—C24—C23−3.7 (6)
C10—C11—C12—C134.8 (5)C18—C19—C24—C23175.4 (4)
C6—C5—C13—C15174.0 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5C···O3i0.84 (3)2.13 (3)2.946 (5)164 (6)
O5—H5D···N1ii0.84 (3)2.26 (11)2.924 (6)135 (13)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2309).

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