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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2220.
Published online 2009 July 22. doi:  10.1107/S1600536809028293
PMCID: PMC2970074

(8S,9R,10S,11S,13S,14S,16S,17R)-4,4-Dichloro-16β-methyl-3,20-dioxo-17,21-bis­(propano­yloxy)-5β,8β-epoxy­pregna-1,9-diene

Abstract

The title compound, C28H34Cl2O7, is a derivative of the glucocorticoid steroid beclomethasone dipropionate. It features an expoxide linkage [angle at oxygen = 96.6 (2)°]. The dichlorocyclohexenone ring adopts an envelope conformation, with the C atom bearing the two Cl substituents representing the flap. The dichloro­methyl C atom deviates by 0.471 (4) Å from the plane defined by the other five atoms, whose maximum r.m.s. deviation is 0.04 Å.

Related literature

For related structures, see: Ketuly et al. (2009a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2220-scheme1.jpg

Experimental

Crystal data

  • C28H34Cl2O7
  • M r = 553.45
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2220-efi1.jpg
  • a = 11.1556 (2) Å
  • b = 12.2281 (2) Å
  • c = 19.3476 (4) Å
  • V = 2639.24 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.29 mm−1
  • T = 140 K
  • 0.30 × 0.15 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.918, T max = 0.971
  • 24071 measured reflections
  • 6067 independent reflections
  • 4878 reflections with I > 2σ(I)
  • R int = 0.083

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.116
  • S = 1.03
  • 6067 reflections
  • 339 parameters
  • H-atom parameters constrained
  • Δρmax = 0.45 e Å−3
  • Δρmin = −0.29 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3199 Friedel pairs
  • Flack parameter: −0.16 (6)

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]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028293/bt5010sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028293/bt5010Isup2.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

The synthesis of the compound is described in a 1988 study commissioned by the Glaxo company (now called Glaxo Smith Kline), External Report No. WAP/88/007. Crystals were grown from its solution in ethyl acetate; m.p. 492–493 K. C7H elemental analysis. Calc. for C28H34Cl2O7 (MW 552): C 60.87, H, 6.15, Cl 14.26%. Found C 61.36, H 6.33, Cl 14.26 %.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.99 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times Ueq(C).

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C28H34Cl2O7 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C28H34Cl2O7F(000) = 1168
Mr = 553.45Dx = 1.393 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6462 reflections
a = 11.1556 (2) Åθ = 2.5–28.0°
b = 12.2281 (2) ŵ = 0.29 mm1
c = 19.3476 (4) ÅT = 140 K
V = 2639.24 (8) Å3Multiple crystalline block, colorless
Z = 40.30 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer6067 independent reflections
Radiation source: fine-focus sealed tube4878 reflections with I > 2σ(I)
graphiteRint = 0.083
ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −14→14
Tmin = 0.918, Tmax = 0.971k = −15→15
24071 measured reflectionsl = −24→25

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.116w = 1/[σ2(Fo2) + (0.0588P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
6067 reflectionsΔρmax = 0.45 e Å3
339 parametersΔρmin = −0.29 e Å3
0 restraintsAbsolute structure: Flack (1983), 3199 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.16 (6)

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

xyzUiso*/Ueq
Cl10.59256 (6)0.63874 (6)0.83223 (4)0.03035 (17)
Cl20.40010 (7)0.78271 (6)0.78724 (3)0.02583 (16)
O10.5154 (2)0.76634 (19)0.94879 (11)0.0395 (6)
O20.39813 (17)0.49261 (14)0.87881 (9)0.0186 (4)
O30.23417 (17)0.17101 (16)1.02004 (9)0.0207 (4)
O40.30538 (19)0.00381 (17)1.04842 (10)0.0270 (5)
O50.1490 (2)−0.00893 (18)0.88479 (11)0.0311 (5)
O6−0.04283 (18)−0.03711 (18)0.96500 (10)0.0289 (5)
O7−0.1240 (2)0.0925 (2)0.89835 (13)0.0441 (6)
C10.4397 (2)0.6766 (2)0.84723 (14)0.0217 (6)
C20.4287 (3)0.7295 (2)0.91964 (14)0.0247 (6)
C30.3070 (3)0.7333 (2)0.94717 (14)0.0276 (6)
H30.29130.78070.98500.033*
C40.2167 (3)0.6739 (2)0.92216 (14)0.0245 (6)
H40.14160.68010.94500.029*
C50.2229 (2)0.5983 (2)0.86127 (14)0.0203 (6)
C60.1319 (3)0.6378 (3)0.80715 (15)0.0280 (7)
H6A0.05280.64480.82870.042*
H6B0.12780.58490.76920.042*
H6C0.15720.70910.78910.042*
C70.3561 (2)0.5809 (2)0.83546 (14)0.0190 (5)
C80.3576 (3)0.5283 (2)0.76388 (14)0.0233 (6)
H8A0.43960.52600.74430.028*
H8B0.30370.56700.73140.028*
C90.3107 (3)0.4125 (2)0.78109 (14)0.0244 (6)
H9A0.23100.39960.76010.029*
H9B0.36710.35550.76480.029*
C100.3032 (2)0.4144 (2)0.86073 (13)0.0184 (5)
C110.1961 (2)0.4800 (2)0.88369 (13)0.0186 (5)
C120.1084 (3)0.4403 (2)0.92204 (14)0.0227 (6)
H120.04620.48850.93610.027*
C130.1017 (3)0.3215 (2)0.94484 (14)0.0233 (6)
H13A0.02020.29310.93560.028*
H13B0.11600.31730.99530.028*
C140.1939 (3)0.2494 (2)0.90729 (13)0.0209 (6)
C150.1423 (3)0.2191 (3)0.83575 (15)0.0272 (6)
H15A0.11880.28580.81120.041*
H15B0.07200.17200.84180.041*
H15C0.20330.18010.80890.041*
C160.3147 (2)0.3108 (2)0.90233 (13)0.0188 (6)
H160.33700.33290.95040.023*
C170.4044 (3)0.2242 (2)0.87993 (14)0.0234 (6)
H17A0.48750.24760.89000.028*
H17B0.39710.20860.82990.028*
C180.3695 (2)0.1232 (2)0.92347 (15)0.0229 (6)
H180.41930.12640.96640.027*
C190.4019 (3)0.0166 (2)0.88754 (17)0.0334 (7)
H19A0.3769−0.04520.91640.050*
H19B0.48880.01350.88030.050*
H19C0.36090.01280.84280.050*
C200.2361 (2)0.1420 (2)0.94671 (13)0.0203 (6)
C210.2739 (2)0.0941 (2)1.06562 (14)0.0223 (6)
C220.2662 (3)0.1371 (3)1.13866 (14)0.0309 (7)
H22A0.18110.13961.15300.037*
H22B0.29790.21271.13990.037*
C230.3360 (3)0.0672 (3)1.18969 (15)0.0304 (7)
H23A0.32590.09671.23640.046*
H23B0.42120.06781.17730.046*
H23C0.3058−0.00811.18820.046*
C240.1462 (2)0.0488 (2)0.93501 (14)0.0214 (6)
C250.0457 (3)0.0390 (3)0.98795 (15)0.0300 (7)
H25A0.07920.01431.03270.036*
H25B0.00820.11150.99510.036*
C26−0.1214 (3)0.0001 (3)0.91806 (15)0.0277 (7)
C27−0.2012 (3)−0.0907 (3)0.89423 (15)0.0295 (7)
H27A−0.2541−0.06330.85700.035*
H27B−0.2526−0.11450.93310.035*
C28−0.1304 (3)−0.1883 (3)0.86761 (19)0.0401 (8)
H28A−0.1857−0.24250.84820.060*
H28B−0.0853−0.22120.90580.060*
H28C−0.0745−0.16400.83160.060*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0214 (3)0.0217 (4)0.0479 (4)−0.0017 (3)0.0023 (3)0.0073 (3)
Cl20.0363 (4)0.0168 (3)0.0244 (3)−0.0009 (3)−0.0006 (3)0.0060 (3)
O10.0536 (14)0.0287 (14)0.0360 (11)−0.0118 (11)−0.0154 (11)0.0019 (10)
O20.0217 (9)0.0123 (9)0.0219 (9)−0.0012 (8)0.0006 (8)0.0013 (7)
O30.0273 (10)0.0186 (10)0.0162 (9)−0.0005 (8)0.0001 (7)−0.0002 (7)
O40.0384 (11)0.0173 (11)0.0253 (10)0.0010 (9)0.0021 (9)0.0009 (8)
O50.0447 (12)0.0225 (12)0.0260 (11)−0.0040 (10)0.0010 (9)−0.0058 (9)
O60.0312 (11)0.0301 (13)0.0253 (10)−0.0109 (9)−0.0033 (9)0.0064 (9)
O70.0477 (15)0.0265 (13)0.0581 (16)0.0041 (11)−0.0032 (11)0.0130 (11)
C10.0258 (14)0.0157 (14)0.0234 (14)0.0028 (11)−0.0012 (11)0.0039 (11)
C20.0393 (18)0.0135 (14)0.0214 (13)−0.0032 (13)−0.0081 (12)0.0036 (11)
C30.0491 (18)0.0150 (15)0.0185 (13)0.0053 (13)0.0004 (13)−0.0009 (11)
C40.0325 (15)0.0195 (15)0.0215 (13)0.0060 (13)0.0046 (12)0.0033 (11)
C50.0200 (13)0.0175 (15)0.0234 (13)−0.0016 (11)0.0042 (11)0.0027 (11)
C60.0304 (15)0.0232 (16)0.0305 (16)0.0000 (13)−0.0024 (12)0.0066 (12)
C70.0224 (12)0.0157 (14)0.0188 (13)0.0017 (11)−0.0008 (10)0.0008 (11)
C80.0315 (14)0.0196 (15)0.0188 (14)0.0028 (12)0.0041 (11)0.0006 (11)
C90.0338 (15)0.0176 (14)0.0219 (14)−0.0020 (12)0.0002 (12)0.0004 (12)
C100.0202 (13)0.0153 (14)0.0197 (12)−0.0042 (11)−0.0003 (10)−0.0003 (10)
C110.0241 (13)0.0131 (13)0.0188 (13)0.0007 (11)−0.0041 (10)−0.0002 (10)
C120.0233 (14)0.0201 (14)0.0247 (14)0.0052 (12)0.0002 (11)−0.0004 (11)
C130.0218 (13)0.0218 (15)0.0262 (14)−0.0003 (12)0.0030 (12)0.0018 (11)
C140.0248 (13)0.0165 (15)0.0213 (13)−0.0029 (11)0.0010 (11)0.0013 (10)
C150.0338 (15)0.0212 (15)0.0267 (14)−0.0063 (13)−0.0049 (12)0.0042 (12)
C160.0211 (12)0.0167 (14)0.0187 (13)0.0004 (11)0.0024 (10)−0.0033 (10)
C170.0275 (13)0.0155 (13)0.0271 (13)0.0013 (13)0.0052 (12)0.0017 (11)
C180.0272 (14)0.0200 (15)0.0214 (13)0.0007 (12)0.0023 (11)0.0002 (11)
C190.0389 (16)0.0170 (15)0.0442 (18)0.0054 (14)0.0131 (15)−0.0002 (13)
C200.0239 (13)0.0189 (14)0.0180 (12)−0.0006 (11)−0.0003 (10)−0.0019 (11)
C210.0219 (13)0.0233 (16)0.0217 (13)−0.0040 (12)−0.0013 (10)0.0007 (11)
C220.0422 (18)0.0297 (18)0.0209 (14)0.0024 (15)0.0012 (12)−0.0021 (12)
C230.0331 (16)0.0353 (19)0.0228 (15)−0.0038 (14)−0.0012 (12)0.0011 (13)
C240.0269 (14)0.0166 (14)0.0208 (14)−0.0024 (12)−0.0003 (11)0.0014 (11)
C250.0292 (15)0.0348 (19)0.0259 (15)−0.0137 (14)0.0019 (12)−0.0008 (13)
C260.0304 (16)0.0291 (17)0.0238 (14)0.0015 (13)0.0033 (12)0.0048 (12)
C270.0272 (15)0.0389 (19)0.0224 (14)−0.0047 (14)−0.0033 (12)0.0041 (13)
C280.046 (2)0.0324 (19)0.0417 (19)−0.0022 (15)−0.0091 (15)−0.0061 (15)

Geometric parameters (Å, °)

Cl1—C11.791 (3)C13—H13A0.9900
Cl2—C11.796 (3)C13—H13B0.9900
O1—C21.207 (3)C14—C151.545 (4)
O2—C71.445 (3)C14—C161.546 (4)
O2—C101.470 (3)C14—C201.590 (4)
O3—C211.364 (3)C15—H15A0.9800
O3—C201.463 (3)C15—H15B0.9800
O4—C211.205 (4)C15—H15C0.9800
O5—C241.201 (3)C16—C171.520 (4)
O6—C261.341 (3)C16—H161.0000
O6—C251.428 (4)C17—C181.545 (4)
O7—C261.193 (4)C17—H17A0.9900
C1—C71.514 (4)C17—H17B0.9900
C1—C21.548 (4)C18—C191.521 (4)
C2—C31.458 (4)C18—C201.572 (4)
C3—C41.332 (4)C18—H181.0000
C3—H30.9500C19—H19A0.9800
C4—C51.500 (4)C19—H19B0.9800
C4—H40.9500C19—H19C0.9800
C5—C61.536 (4)C20—C241.535 (4)
C5—C111.539 (4)C21—C221.510 (4)
C5—C71.583 (4)C22—C231.520 (4)
C6—H6A0.9800C22—H22A0.9900
C6—H6B0.9800C22—H22B0.9900
C6—H6C0.9800C23—H23A0.9800
C7—C81.527 (4)C23—H23B0.9800
C8—C91.546 (4)C23—H23C0.9800
C8—H8A0.9900C24—C251.523 (4)
C8—H8B0.9900C25—H25A0.9900
C9—C101.543 (4)C25—H25B0.9900
C9—H9A0.9900C26—C271.496 (4)
C9—H9B0.9900C27—C281.521 (5)
C10—C111.505 (4)C27—H27A0.9900
C10—C161.506 (4)C27—H27B0.9900
C11—C121.321 (4)C28—H28A0.9800
C12—C131.519 (4)C28—H28B0.9800
C12—H120.9500C28—H28C0.9800
C13—C141.538 (4)
C7—O2—C1096.57 (18)H15A—C15—H15B109.5
C21—O3—C20117.1 (2)C14—C15—H15C109.5
C26—O6—C25116.2 (3)H15A—C15—H15C109.5
C7—C1—C2114.2 (2)H15B—C15—H15C109.5
C7—C1—Cl1111.2 (2)C10—C16—C17119.3 (2)
C2—C1—Cl1109.30 (19)C10—C16—C14111.5 (2)
C7—C1—Cl2108.06 (19)C17—C16—C14104.7 (2)
C2—C1—Cl2105.28 (19)C10—C16—H16106.9
Cl1—C1—Cl2108.43 (15)C17—C16—H16106.9
O1—C2—C3124.3 (3)C14—C16—H16106.9
O1—C2—C1121.0 (3)C16—C17—C18103.7 (2)
C3—C2—C1114.7 (2)C16—C17—H17A111.0
C4—C3—C2123.6 (3)C18—C17—H17A111.0
C4—C3—H3118.2C16—C17—H17B111.0
C2—C3—H3118.2C18—C17—H17B111.0
C3—C4—C5125.9 (3)H17A—C17—H17B109.0
C3—C4—H4117.0C19—C18—C17112.1 (2)
C5—C4—H4117.0C19—C18—C20118.7 (3)
C4—C5—C6108.1 (2)C17—C18—C20106.1 (2)
C4—C5—C11110.5 (2)C19—C18—H18106.4
C6—C5—C11111.1 (2)C17—C18—H18106.4
C4—C5—C7111.9 (2)C20—C18—H18106.4
C6—C5—C7116.6 (2)C18—C19—H19A109.5
C11—C5—C798.3 (2)C18—C19—H19B109.5
C5—C6—H6A109.5H19A—C19—H19B109.5
C5—C6—H6B109.5C18—C19—H19C109.5
H6A—C6—H6B109.5H19A—C19—H19C109.5
C5—C6—H6C109.5H19B—C19—H19C109.5
H6A—C6—H6C109.5O3—C20—C24108.3 (2)
H6B—C6—H6C109.5O3—C20—C18109.1 (2)
O2—C7—C1106.9 (2)C24—C20—C18117.9 (2)
O2—C7—C8102.0 (2)O3—C20—C14105.1 (2)
C1—C7—C8117.1 (2)C24—C20—C14110.5 (2)
O2—C7—C5102.8 (2)C18—C20—C14105.3 (2)
C1—C7—C5115.3 (2)O4—C21—O3123.2 (2)
C8—C7—C5110.7 (2)O4—C21—C22126.4 (3)
C7—C8—C9100.7 (2)O3—C21—C22110.3 (2)
C7—C8—H8A111.6C21—C22—C23112.5 (3)
C9—C8—H8A111.6C21—C22—H22A109.1
C7—C8—H8B111.6C23—C22—H22A109.1
C9—C8—H8B111.6C21—C22—H22B109.1
H8A—C8—H8B109.4C23—C22—H22B109.1
C10—C9—C8102.7 (2)H22A—C22—H22B107.8
C10—C9—H9A111.2C22—C23—H23A109.5
C8—C9—H9A111.2C22—C23—H23B109.5
C10—C9—H9B111.2H23A—C23—H23B109.5
C8—C9—H9B111.2C22—C23—H23C109.5
H9A—C9—H9B109.1H23A—C23—H23C109.5
O2—C10—C1198.9 (2)H23B—C23—H23C109.5
O2—C10—C16111.0 (2)O5—C24—C25121.1 (3)
C11—C10—C16111.0 (2)O5—C24—C20122.6 (3)
O2—C10—C9102.0 (2)C25—C24—C20116.1 (2)
C11—C10—C9110.2 (2)O6—C25—C24110.6 (2)
C16—C10—C9121.1 (2)O6—C25—H25A109.5
C12—C11—C10123.9 (3)C24—C25—H25A109.5
C12—C11—C5130.3 (3)O6—C25—H25B109.5
C10—C11—C5105.3 (2)C24—C25—H25B109.5
C11—C12—C13123.4 (3)H25A—C25—H25B108.1
C11—C12—H12118.3O7—C26—O6123.6 (3)
C13—C12—H12118.3O7—C26—C27126.2 (3)
C12—C13—C14112.3 (2)O6—C26—C27110.2 (3)
C12—C13—H13A109.2C26—C27—C28112.2 (3)
C14—C13—H13A109.2C26—C27—H27A109.2
C12—C13—H13B109.2C28—C27—H27A109.2
C14—C13—H13B109.2C26—C27—H27B109.2
H13A—C13—H13B107.9C28—C27—H27B109.2
C13—C14—C15108.2 (2)H27A—C27—H27B107.9
C13—C14—C16109.5 (2)C27—C28—H28A109.5
C15—C14—C16112.7 (2)C27—C28—H28B109.5
C13—C14—C20116.4 (2)H28A—C28—H28B109.5
C15—C14—C20110.0 (2)C27—C28—H28C109.5
C16—C14—C20100.0 (2)H28A—C28—H28C109.5
C14—C15—H15A109.5H28B—C28—H28C109.5
C14—C15—H15B109.5
C7—C1—C2—O1145.1 (3)C5—C11—C12—C13−174.1 (3)
Cl1—C1—C2—O119.8 (3)C11—C12—C13—C14−10.9 (4)
Cl2—C1—C2—O1−96.5 (3)C12—C13—C14—C15−81.5 (3)
C7—C1—C2—C3−36.6 (3)C12—C13—C14—C1641.7 (3)
Cl1—C1—C2—C3−162.0 (2)C12—C13—C14—C20154.1 (2)
Cl2—C1—C2—C381.7 (3)O2—C10—C16—C17−80.9 (3)
O1—C2—C3—C4−165.8 (3)C11—C10—C16—C17170.1 (2)
C1—C2—C3—C416.0 (4)C9—C10—C16—C1738.5 (4)
C2—C3—C4—C5−2.5 (5)O2—C10—C16—C14156.8 (2)
C3—C4—C5—C6−120.7 (3)C11—C10—C16—C1447.9 (3)
C3—C4—C5—C11117.5 (3)C9—C10—C16—C14−83.7 (3)
C3—C4—C5—C79.1 (4)C13—C14—C16—C10−62.1 (3)
C10—O2—C7—C1177.9 (2)C15—C14—C16—C1058.3 (3)
C10—O2—C7—C8−58.6 (2)C20—C14—C16—C10175.1 (2)
C10—O2—C7—C556.1 (2)C13—C14—C16—C17167.5 (2)
C2—C1—C7—O2−69.4 (3)C15—C14—C16—C17−72.0 (3)
Cl1—C1—C7—O254.9 (2)C20—C14—C16—C1744.7 (2)
Cl2—C1—C7—O2173.80 (16)C10—C16—C17—C18−167.4 (2)
C2—C1—C7—C8177.0 (2)C14—C16—C17—C18−41.8 (3)
Cl1—C1—C7—C8−58.7 (3)C16—C17—C18—C19152.0 (2)
Cl2—C1—C7—C860.2 (3)C16—C17—C18—C2020.9 (3)
C2—C1—C7—C544.1 (3)C21—O3—C20—C2465.7 (3)
Cl1—C1—C7—C5168.45 (18)C21—O3—C20—C18−63.7 (3)
Cl2—C1—C7—C5−72.6 (2)C21—O3—C20—C14−176.2 (2)
C4—C5—C7—O286.0 (3)C19—C18—C20—O3126.9 (3)
C6—C5—C7—O2−148.8 (2)C17—C18—C20—O3−105.9 (2)
C11—C5—C7—O2−30.1 (2)C19—C18—C20—C243.0 (4)
C4—C5—C7—C1−29.9 (3)C17—C18—C20—C24130.2 (3)
C6—C5—C7—C195.3 (3)C19—C18—C20—C14−120.7 (3)
C11—C5—C7—C1−146.0 (2)C17—C18—C20—C146.5 (3)
C4—C5—C7—C8−165.7 (2)C13—C14—C20—O3−33.2 (3)
C6—C5—C7—C8−40.5 (3)C15—C14—C20—O3−156.7 (2)
C11—C5—C7—C878.2 (2)C16—C14—C20—O384.6 (2)
O2—C7—C8—C939.8 (2)C13—C14—C20—C2483.4 (3)
C1—C7—C8—C9156.1 (2)C15—C14—C20—C24−40.1 (3)
C5—C7—C8—C9−69.1 (3)C16—C14—C20—C24−158.8 (2)
C7—C8—C9—C10−5.8 (3)C13—C14—C20—C18−148.3 (2)
C7—O2—C10—C11−59.3 (2)C15—C14—C20—C1888.2 (3)
C7—O2—C10—C16−175.9 (2)C16—C14—C20—C18−30.6 (2)
C7—O2—C10—C953.8 (2)C20—O3—C21—O4−2.9 (4)
C8—C9—C10—O2−29.0 (3)C20—O3—C21—C22179.8 (2)
C8—C9—C10—C1175.3 (3)O4—C21—C22—C2316.6 (4)
C8—C9—C10—C16−152.8 (2)O3—C21—C22—C23−166.2 (2)
O2—C10—C11—C12−132.5 (3)O3—C20—C24—O5−161.5 (3)
C16—C10—C11—C12−15.8 (4)C18—C20—C24—O5−37.1 (4)
C9—C10—C11—C12121.2 (3)C14—C20—C24—O583.9 (3)
O2—C10—C11—C540.5 (2)O3—C20—C24—C2523.5 (3)
C16—C10—C11—C5157.1 (2)C18—C20—C24—C25147.9 (3)
C9—C10—C11—C5−65.9 (3)C14—C20—C24—C25−91.1 (3)
C4—C5—C11—C1248.3 (4)C26—O6—C25—C24−79.3 (3)
C6—C5—C11—C12−71.6 (4)O5—C24—C25—O6−5.4 (4)
C7—C5—C11—C12165.6 (3)C20—C24—C25—O6169.7 (2)
C4—C5—C11—C10−124.0 (2)C25—O6—C26—O7−4.1 (4)
C6—C5—C11—C10116.1 (2)C25—O6—C26—C27174.9 (2)
C7—C5—C11—C10−6.7 (2)O7—C26—C27—C28124.6 (4)
C10—C11—C12—C13−3.1 (4)O6—C26—C27—C28−54.3 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5010).

References

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