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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1821.
Published online 2009 July 11. doi:  10.1107/S1600536809025975
PMCID: PMC2977184

9α-Bromo analog of beclometasone dipropionate monohydrate

Abstract

In the crystal structure of (8S,9R,10S,11S,13S,14S,16S,17R)-9α-bromo-11-hydr­oxy-10,13,16-trimethyl-3-oxo-17-[2-(propion­yloxy)acet­yl]-6,7,8,9,10,11,12,13,14,15,16,17-dodeca­hydro-3H-cyclo­penta­[a]phenanthren-17-yl propionate monohydrate, C28H37BrO7·H2O, which has a 9α-Br atom in place of the 9α-Cl atom of monohydrated beclometasone dipropionate, one six-membered ring is planar (r.m.s. deviation = 0.02 Å) owing to its 1,4-diene-3-one composition, whereas the two other six-membered rings each have a chair conformation. The organic mol­ecule and water mol­ecules engage in hydrogen-bonding inter­actions, generating a helical chain running along the c axis of the ortho­rhom­bic unit cell.

Related literature

For the NMR data and the crystal structure of the asthma drug beclometasone dipropionate monohydrate, see: Othman et al. (2008 [triangle]); Duax et al. (1981 [triangle]). The two compounds are isostructural.

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Object name is e-65-o1821-scheme1.jpg

Experimental

Crystal data

  • C28H37BrO7·H2O
  • M r = 583.50
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1821-efi1.jpg
  • a = 11.9565 (2) Å
  • b = 14.1329 (2) Å
  • c = 16.1648 (3) Å
  • V = 2731.53 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.55 mm−1
  • T = 140 K
  • 0.40 × 0.08 × 0.08 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.611, T max = 0.746 (expected range = 0.723–0.883)
  • 18917 measured reflections
  • 6226 independent reflections
  • 5575 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.026
  • wR(F 2) = 0.055
  • S = 0.96
  • 6226 reflections
  • 351 parameters
  • 4 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.39 e Å−3
  • Δρmin = −0.25 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2717 Friedel pairs
  • Flack parameter: 0.001 (5)

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025975/tk2488sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025975/tk2488Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

17α,21-Dihydroxy-16β-methylpregna-1,4,9-triene-3,20-dionedipropionate (5.5 g) was reacted with bromodan (1,3-dibromo-5,5-dimethylhydantion) (4.8 g) to give a yellow product (6.6 g). TLC showed one major product and five minor ones. The major product (3.0 g) was initially recrystallized three times, once from chloroform-methanol (1:2 v/v), and the second and third times from hexane-methanol (1:1 v/v). The recovered material (1.8 g). was then divided for two different recrystallizations.

Recrystallization form ethyl acetate-methanol (1:9 v/v) gave a white powder, m.p. 453–455 K. Elemental analysis: Calc. for C28H37BrO7 (mol. wt. 564): C 59.47, H 6.59, Br 14.13%. Found: C 59.3, H 6.57, Br 13.83%.

Recrystallization from methanol water gave colorless crystals, m.p. 460–461 K. Elemental analysis: Calc. for C22H37BrO7.H2O (mol. wt. 582): C 57.64, H 6.69, Br 13.70%. Found: C 57.68, H 6.78, Br 13.46%. The water molecule was detected from the 1H-NMR spectrum. Thermogravimetric analysis showed a peak at 365 K that corresponded to the loss of water.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.95–1.00 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times Ueq(C). The O-H atoms were refined with 0.84 (1) Å and with U(H) set to 1.5 times Ueq(O).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C28H37BrO7.H2O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C28H37BrO7·H2OF(000) = 1224
Mr = 583.50Dx = 1.419 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7177 reflections
a = 11.9565 (2) Åθ = 2.2–28.2°
b = 14.1329 (2) ŵ = 1.55 mm1
c = 16.1648 (3) ÅT = 140 K
V = 2731.53 (8) Å3Prism, brown
Z = 40.40 × 0.08 × 0.08 mm

Data collection

Bruker SMART APEX diffractometer6226 independent reflections
Radiation source: fine-focus sealed tube5575 reflections with I > 2σ(I)
graphiteRint = 0.028
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −15→15
Tmin = 0.611, Tmax = 0.746k = −18→18
18917 measured reflectionsl = −20→21

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.055w = 1/[σ2(Fo2) + (0.0102P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max = 0.001
6226 reflectionsΔρmax = 0.39 e Å3
351 parametersΔρmin = −0.25 e Å3
4 restraintsAbsolute structure: Flack (1983), 2717 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.001 (5)

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

xyzUiso*/Ueq
Br10.657482 (17)0.615717 (12)0.957131 (12)0.01918 (5)
O10.66966 (16)0.34385 (10)0.78558 (10)0.0357 (4)
O20.81449 (12)0.80839 (9)0.80872 (9)0.0228 (3)
H20.8635 (13)0.8476 (11)0.8218 (12)0.018 (6)*
O30.67741 (12)1.10469 (9)1.01228 (9)0.0272 (3)
O40.86491 (12)1.09748 (9)1.10396 (9)0.0247 (3)
O50.93019 (13)1.02972 (10)0.98878 (9)0.0275 (4)
O60.64117 (12)0.87198 (8)1.09415 (7)0.0177 (3)
O70.56588 (13)0.95956 (9)1.19554 (9)0.0233 (3)
O1W0.98752 (14)0.93262 (10)0.83951 (10)0.0274 (3)
H110.989 (2)0.9626 (15)0.8845 (8)0.042 (8)*
H120.975 (3)0.9715 (14)0.8012 (10)0.061 (10)*
C10.6947 (2)0.69388 (14)0.69871 (12)0.0247 (5)
H1A0.68440.65030.65210.037*
H1B0.76950.72220.69570.037*
H1C0.63810.74390.69610.037*
C20.68233 (17)0.63823 (12)0.78206 (12)0.0191 (4)
C30.78273 (19)0.57607 (15)0.78750 (13)0.0225 (5)
H30.85370.60580.79230.027*
C40.7804 (2)0.48178 (14)0.78608 (13)0.0249 (5)
H40.84870.44740.78730.030*
C50.6745 (2)0.43061 (14)0.78268 (13)0.0250 (5)
C60.57302 (19)0.48835 (14)0.77512 (12)0.0222 (5)
H60.50310.45700.76960.027*
C70.57411 (18)0.58267 (14)0.77566 (12)0.0195 (4)
C80.46949 (17)0.64072 (13)0.77038 (13)0.0207 (4)
H8A0.40360.59830.76930.025*
H8B0.47000.67790.71850.025*
C90.46048 (17)0.70818 (13)0.84465 (13)0.0198 (4)
H9A0.39630.75140.83620.024*
H9B0.44600.67090.89540.024*
C100.56683 (17)0.76670 (12)0.85667 (12)0.0165 (4)
H100.57430.80980.80800.020*
C110.67279 (18)0.70477 (12)0.86053 (11)0.0159 (4)
C120.78016 (17)0.76116 (13)0.88200 (12)0.0178 (4)
H12A0.83970.71460.89700.021*
C130.76505 (16)0.82939 (12)0.95594 (13)0.0162 (4)
H13A0.75970.79191.00750.019*
H13B0.83190.87040.96030.019*
C140.66039 (16)0.89215 (11)0.94808 (11)0.0156 (3)
C150.67492 (18)0.96648 (13)0.87915 (11)0.0197 (4)
H15A0.67750.93470.82530.030*
H15B0.74481.00130.88800.030*
H15C0.61181.01070.88030.030*
C160.55793 (17)0.82829 (13)0.93416 (12)0.0158 (4)
H160.55380.78430.98250.019*
C170.46005 (16)0.89684 (13)0.94236 (12)0.0196 (4)
H17A0.38900.86250.95180.023*
H17B0.45250.93670.89230.023*
C180.49199 (17)0.95706 (13)1.01841 (12)0.0188 (4)
H180.45560.92651.06730.023*
C190.44583 (19)1.05760 (13)1.01391 (14)0.0266 (5)
H19A0.46661.09221.06420.040*
H19B0.36421.05531.00920.040*
H19C0.47711.08990.96550.040*
C200.62151 (17)0.94357 (12)1.02997 (12)0.0172 (4)
C210.69204 (16)1.03130 (12)1.04845 (13)0.0194 (4)
C220.78712 (19)1.02089 (14)1.11030 (13)0.0237 (5)
H22A0.75601.01901.16700.028*
H22B0.82660.96041.10020.028*
C230.93404 (17)1.09329 (12)1.03848 (14)0.0223 (4)
C241.01341 (19)1.17575 (13)1.03599 (16)0.0292 (5)
H24A1.03131.19491.09340.035*
H24B0.97581.22981.00870.035*
C251.1207 (2)1.15487 (16)0.99096 (16)0.0361 (6)
H25A1.16571.21260.98750.054*
H25B1.10361.13220.93510.054*
H25C1.16251.10611.02100.054*
C260.60442 (16)0.88507 (15)1.17195 (11)0.0194 (4)
C270.6195 (2)0.79691 (15)1.22196 (13)0.0289 (5)
H27A0.57400.74591.19680.035*
H27B0.69890.77741.21860.035*
C280.5879 (3)0.80587 (18)1.31099 (15)0.0490 (8)
H28A0.60520.74671.33990.074*
H28B0.50770.81901.31540.074*
H28C0.63030.85781.33620.074*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.02274 (10)0.01686 (8)0.01795 (8)0.00030 (8)0.00010 (9)0.00231 (8)
O10.0466 (12)0.0182 (7)0.0421 (10)0.0026 (8)0.0022 (9)−0.0055 (7)
O20.0226 (9)0.0247 (7)0.0211 (7)−0.0069 (6)0.0043 (7)−0.0014 (6)
O30.0291 (9)0.0165 (6)0.0361 (8)0.0000 (6)−0.0037 (7)0.0020 (6)
O40.0224 (9)0.0257 (7)0.0261 (7)−0.0047 (6)0.0011 (6)−0.0071 (6)
O50.0310 (9)0.0239 (7)0.0276 (8)−0.0022 (7)0.0026 (7)−0.0074 (6)
O60.0216 (8)0.0173 (6)0.0143 (6)0.0028 (6)0.0019 (6)0.0018 (5)
O70.0281 (9)0.0220 (7)0.0197 (7)0.0036 (6)0.0027 (7)−0.0024 (6)
O1W0.0315 (9)0.0279 (8)0.0227 (8)−0.0049 (7)0.0016 (8)0.0012 (7)
C10.0295 (13)0.0280 (10)0.0167 (10)−0.0050 (9)0.0023 (9)−0.0016 (9)
C20.0230 (12)0.0189 (9)0.0154 (9)−0.0001 (7)0.0016 (8)−0.0032 (7)
C30.0189 (12)0.0286 (10)0.0201 (11)−0.0006 (9)−0.0001 (9)−0.0060 (9)
C40.0265 (13)0.0236 (10)0.0247 (11)0.0069 (9)0.0007 (10)−0.0061 (9)
C50.0322 (15)0.0238 (10)0.0191 (10)0.0031 (10)0.0026 (11)−0.0045 (8)
C60.0248 (12)0.0252 (10)0.0165 (10)−0.0048 (9)0.0005 (9)−0.0045 (8)
C70.0231 (12)0.0231 (9)0.0122 (9)−0.0011 (9)0.0013 (9)−0.0029 (8)
C80.0191 (11)0.0221 (10)0.0210 (10)−0.0036 (8)−0.0017 (9)−0.0032 (8)
C90.0170 (11)0.0199 (9)0.0224 (10)−0.0003 (8)−0.0010 (9)−0.0033 (8)
C100.0182 (11)0.0150 (9)0.0162 (10)−0.0001 (8)−0.0005 (9)0.0006 (7)
C110.0197 (11)0.0153 (8)0.0126 (9)−0.0008 (8)0.0014 (9)0.0012 (7)
C120.0161 (11)0.0183 (9)0.0188 (10)0.0012 (8)−0.0001 (9)0.0013 (8)
C130.0142 (10)0.0172 (8)0.0172 (9)0.0006 (7)−0.0018 (9)−0.0004 (9)
C140.0166 (9)0.0138 (7)0.0164 (8)−0.0012 (9)0.0004 (9)−0.0009 (8)
C150.0213 (12)0.0198 (9)0.0180 (9)−0.0014 (8)0.0005 (9)0.0044 (8)
C160.0142 (10)0.0167 (9)0.0167 (10)−0.0002 (7)0.0009 (8)0.0015 (7)
C170.0174 (10)0.0201 (9)0.0211 (11)0.0027 (8)−0.0014 (8)−0.0010 (8)
C180.0180 (11)0.0178 (9)0.0206 (10)0.0013 (8)0.0012 (8)−0.0002 (8)
C190.0231 (12)0.0226 (10)0.0340 (12)0.0070 (9)−0.0008 (10)−0.0039 (9)
C200.0207 (10)0.0155 (8)0.0155 (10)0.0011 (7)−0.0014 (8)0.0015 (8)
C210.0198 (11)0.0189 (8)0.0195 (10)0.0033 (7)0.0026 (9)−0.0041 (9)
C220.0254 (12)0.0251 (10)0.0207 (11)−0.0049 (9)−0.0005 (9)−0.0005 (9)
C230.0232 (11)0.0201 (9)0.0235 (10)0.0025 (7)−0.0033 (10)0.0004 (9)
C240.0259 (12)0.0223 (9)0.0393 (13)−0.0027 (8)−0.0008 (12)−0.0035 (11)
C250.0328 (15)0.0304 (11)0.0450 (14)−0.0057 (10)0.0047 (12)0.0026 (11)
C260.0166 (10)0.0225 (9)0.0191 (10)−0.0013 (9)−0.0005 (8)0.0016 (9)
C270.0391 (15)0.0229 (10)0.0246 (11)0.0033 (10)0.0046 (10)0.0065 (9)
C280.082 (2)0.0397 (14)0.0253 (12)0.0159 (14)0.0129 (15)0.0137 (11)

Geometric parameters (Å, °)

Br1—C112.0140 (17)C12—H12A1.0000
O1—C51.228 (2)C13—C141.539 (2)
O2—C121.420 (2)C13—H13A0.9900
O2—H20.834 (9)C13—H13B0.9900
O3—C211.203 (2)C14—C161.538 (3)
O4—C231.344 (3)C14—C151.541 (2)
O4—C221.431 (2)C14—C201.580 (2)
O5—C231.206 (2)C15—H15A0.9800
O6—C261.345 (2)C15—H15B0.9800
O6—C201.468 (2)C15—H15C0.9800
O7—C261.211 (2)C16—C171.525 (3)
O1W—H110.842 (9)C16—H161.0000
O1W—H120.842 (9)C17—C181.543 (3)
C1—C21.567 (3)C17—H17A0.9900
C1—H1A0.9800C17—H17B0.9900
C1—H1B0.9800C18—C191.526 (3)
C1—H1C0.9800C18—C201.571 (3)
C2—C31.490 (3)C18—H181.0000
C2—C71.517 (3)C19—H19A0.9800
C2—C111.583 (2)C19—H19B0.9800
C3—C41.333 (3)C19—H19C0.9800
C3—H30.9500C20—C211.529 (3)
C4—C51.459 (3)C21—C221.521 (3)
C4—H40.9500C22—H22A0.9900
C5—C61.467 (3)C22—H22B0.9900
C6—C71.333 (3)C23—C241.503 (3)
C6—H60.9500C24—C251.504 (3)
C7—C81.498 (3)C24—H24A0.9900
C8—C91.537 (3)C24—H24B0.9900
C8—H8A0.9900C25—H25A0.9800
C8—H8B0.9900C25—H25B0.9800
C9—C101.529 (3)C25—H25C0.9800
C9—H9A0.9900C26—C271.496 (3)
C9—H9B0.9900C27—C281.493 (3)
C10—C161.529 (3)C27—H27A0.9900
C10—C111.541 (3)C27—H27B0.9900
C10—H101.0000C28—H28A0.9800
C11—C121.550 (3)C28—H28B0.9800
C12—C131.546 (3)C28—H28C0.9800
C12—O2—H2107.7 (15)C14—C15—H15B109.5
C23—O4—C22115.02 (15)H15A—C15—H15B109.5
C26—O6—C20120.91 (14)C14—C15—H15C109.5
H11—O1W—H12108.1 (14)H15A—C15—H15C109.5
C2—C1—H1A109.5H15B—C15—H15C109.5
C2—C1—H1B109.5C17—C16—C10119.09 (16)
H1A—C1—H1B109.5C17—C16—C14103.05 (14)
C2—C1—H1C109.5C10—C16—C14113.48 (15)
H1A—C1—H1C109.5C17—C16—H16106.8
H1B—C1—H1C109.5C10—C16—H16106.8
C3—C2—C7112.70 (16)C14—C16—H16106.8
C3—C2—C1105.68 (17)C16—C17—C18103.28 (15)
C7—C2—C1106.38 (16)C16—C17—H17A111.1
C3—C2—C11111.16 (16)C18—C17—H17A111.1
C7—C2—C11107.50 (16)C16—C17—H17B111.1
C1—C2—C11113.43 (14)C18—C17—H17B111.1
C4—C3—C2124.9 (2)H17A—C17—H17B109.1
C4—C3—H3117.6C19—C18—C17112.71 (16)
C2—C3—H3117.6C19—C18—C20118.36 (16)
C3—C4—C5120.9 (2)C17—C18—C20105.77 (15)
C3—C4—H4119.5C19—C18—H18106.4
C5—C4—H4119.5C17—C18—H18106.4
O1—C5—C4122.3 (2)C20—C18—H18106.4
O1—C5—C6121.3 (2)C18—C19—H19A109.5
C4—C5—C6116.43 (17)C18—C19—H19B109.5
C7—C6—C5123.2 (2)H19A—C19—H19B109.5
C7—C6—H6118.4C18—C19—H19C109.5
C5—C6—H6118.4H19A—C19—H19C109.5
C6—C7—C8122.6 (2)H19B—C19—H19C109.5
C6—C7—C2121.8 (2)O6—C20—C21109.42 (15)
C8—C7—C2115.62 (16)O6—C20—C18108.99 (15)
C7—C8—C9110.72 (17)C21—C20—C18117.93 (15)
C7—C8—H8A109.5O6—C20—C14103.17 (13)
C9—C8—H8A109.5C21—C20—C14111.98 (15)
C7—C8—H8B109.5C18—C20—C14104.25 (15)
C9—C8—H8B109.5O3—C21—C22120.75 (17)
H8A—C8—H8B108.1O3—C21—C20121.59 (18)
C10—C9—C8112.12 (17)C22—C21—C20117.53 (16)
C10—C9—H9A109.2O4—C22—C21111.44 (16)
C8—C9—H9A109.2O4—C22—H22A109.3
C10—C9—H9B109.2C21—C22—H22A109.3
C8—C9—H9B109.2O4—C22—H22B109.3
H9A—C9—H9B107.9C21—C22—H22B109.3
C9—C10—C16110.74 (16)H22A—C22—H22B108.0
C9—C10—C11112.43 (15)O5—C23—O4122.26 (18)
C16—C10—C11110.33 (16)O5—C23—C24125.7 (2)
C9—C10—H10107.7O4—C23—C24112.03 (17)
C16—C10—H10107.7C23—C24—C25113.52 (17)
C11—C10—H10107.7C23—C24—H24A108.9
C10—C11—C12113.44 (14)C25—C24—H24A108.9
C10—C11—C2111.36 (15)C23—C24—H24B108.9
C12—C11—C2115.16 (16)C25—C24—H24B108.9
C10—C11—Br1108.15 (13)H24A—C24—H24B107.7
C12—C11—Br1102.88 (12)C24—C25—H25A109.5
C2—C11—Br1104.87 (11)C24—C25—H25B109.5
O2—C12—C13112.67 (15)H25A—C25—H25B109.5
O2—C12—C11107.10 (15)C24—C25—H25C109.5
C13—C12—C11113.39 (16)H25A—C25—H25C109.5
O2—C12—H12A107.8H25B—C25—H25C109.5
C13—C12—H12A107.8O7—C26—O6122.58 (18)
C11—C12—H12A107.8O7—C26—C27126.86 (18)
C14—C13—C12112.99 (16)O6—C26—C27110.56 (17)
C14—C13—H13A109.0C28—C27—C26114.81 (19)
C12—C13—H13A109.0C28—C27—H27A108.6
C14—C13—H13B109.0C26—C27—H27A108.6
C12—C13—H13B109.0C28—C27—H27B108.6
H13A—C13—H13B107.8C26—C27—H27B108.6
C16—C14—C13108.75 (13)H27A—C27—H27B107.5
C16—C14—C15112.57 (15)C27—C28—H28A109.5
C13—C14—C15111.15 (16)C27—C28—H28B109.5
C16—C14—C2099.10 (14)H28A—C28—H28B109.5
C13—C14—C20115.80 (15)C27—C28—H28C109.5
C15—C14—C20108.99 (13)H28A—C28—H28C109.5
C14—C15—H15A109.5H28B—C28—H28C109.5
C7—C2—C3—C40.7 (3)C11—C10—C16—C17178.77 (15)
C1—C2—C3—C4−115.0 (2)C9—C10—C16—C14−177.67 (15)
C11—C2—C3—C4121.5 (2)C11—C10—C16—C1457.2 (2)
C2—C3—C4—C5−2.9 (3)C13—C14—C16—C17170.68 (15)
C3—C4—C5—O1−176.2 (2)C15—C14—C16—C17−65.69 (18)
C3—C4—C5—C64.1 (3)C20—C14—C16—C1749.36 (16)
O1—C5—C6—C7176.8 (2)C13—C14—C16—C10−59.2 (2)
C4—C5—C6—C7−3.5 (3)C15—C14—C16—C1064.46 (19)
C5—C6—C7—C8−178.16 (18)C20—C14—C16—C10179.52 (15)
C5—C6—C7—C21.6 (3)C10—C16—C17—C18−170.04 (16)
C3—C2—C7—C60.0 (3)C14—C16—C17—C18−43.38 (18)
C1—C2—C7—C6115.3 (2)C16—C17—C18—C19149.83 (17)
C11—C2—C7—C6−122.9 (2)C16—C17—C18—C2019.04 (19)
C3—C2—C7—C8179.71 (17)C26—O6—C20—C2169.4 (2)
C1—C2—C7—C8−64.9 (2)C26—O6—C20—C18−60.9 (2)
C11—C2—C7—C856.9 (2)C26—O6—C20—C14−171.26 (16)
C6—C7—C8—C9123.4 (2)C19—C18—C20—O6134.07 (17)
C2—C7—C8—C9−56.3 (2)C17—C18—C20—O6−98.47 (16)
C7—C8—C9—C1051.6 (2)C19—C18—C20—C218.6 (3)
C8—C9—C10—C16−176.37 (16)C17—C18—C20—C21136.05 (17)
C8—C9—C10—C11−52.4 (2)C19—C18—C20—C14−116.29 (18)
C9—C10—C11—C12−173.84 (16)C17—C18—C20—C1411.17 (18)
C16—C10—C11—C12−49.7 (2)C16—C14—C20—O677.41 (15)
C9—C10—C11—C254.3 (2)C13—C14—C20—O6−38.62 (19)
C16—C10—C11—C2178.48 (14)C15—C14—C20—O6−164.80 (14)
C9—C10—C11—Br1−60.40 (18)C16—C14—C20—C21−165.02 (15)
C16—C10—C11—Br163.76 (16)C13—C14—C20—C2178.94 (19)
C3—C2—C11—C10−177.98 (16)C15—C14—C20—C21−47.2 (2)
C7—C2—C11—C10−54.21 (19)C16—C14—C20—C18−36.43 (16)
C1—C2—C11—C1063.1 (2)C13—C14—C20—C18−152.47 (14)
C3—C2—C11—C1251.1 (2)C15—C14—C20—C1881.36 (18)
C7—C2—C11—C12174.83 (15)O6—C20—C21—O3−168.22 (17)
C1—C2—C11—C12−67.9 (2)C18—C20—C21—O3−42.9 (3)
C3—C2—C11—Br1−61.25 (18)C14—C20—C21—O378.0 (2)
C7—C2—C11—Br162.53 (16)O6—C20—C21—C2215.8 (2)
C1—C2—C11—Br1179.84 (14)C18—C20—C21—C22141.12 (18)
C10—C11—C12—O2−78.15 (19)C14—C20—C21—C22−97.9 (2)
C2—C11—C12—O251.8 (2)C23—O4—C22—C21−75.7 (2)
Br1—C11—C12—O2165.26 (11)O3—C21—C22—O4−13.0 (3)
C10—C11—C12—C1346.8 (2)C20—C21—C22—O4162.93 (17)
C2—C11—C12—C13176.72 (15)C22—O4—C23—O50.3 (3)
Br1—C11—C12—C13−69.82 (16)C22—O4—C23—C24−179.85 (17)
O2—C12—C13—C1472.5 (2)O5—C23—C24—C25−26.0 (3)
C11—C12—C13—C14−49.3 (2)O4—C23—C24—C25154.08 (19)
C12—C13—C14—C1654.1 (2)C20—O6—C26—O7−9.0 (3)
C12—C13—C14—C15−70.40 (19)C20—O6—C26—C27171.58 (17)
C12—C13—C14—C20164.53 (15)O7—C26—C27—C28−3.2 (4)
C9—C10—C16—C17−56.1 (2)O6—C26—C27—C28176.3 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O1w0.83 (1)1.93 (1)2.759 (2)173 (2)
O1w—H11···O50.84 (1)2.06 (1)2.859 (2)159 (3)
O1w—H12···O7i0.84 (1)2.03 (1)2.854 (2)168 (2)

Symmetry codes: (i) −x+3/2, −y+2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2488).

References

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