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The title compound (systematic name: 17-acetyl-16-bromo-17-hydr­oxy-10,13-dimethyl-1,6,7,8,9,10,12,13,14, 15,16,17-dodeca­hydro-2H-cyclo­penta­[a]phenanthrene-3,11-dione chloro­form solvate), C21H27BrO4·CHCl3, is an important intermediate in the synthesis of hormone pharmaceuticals. The asymmetric unit consists of one steroid and one chloro­form mol­ecule. The crystal structure is predominantly stabilized by strong inter­molecular O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012220/hk2025sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012220/hk2025Isup2.hkl
Contains datablock I

CCDC reference: 608353

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.042
  • wR factor = 0.091
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.26 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.85 Ratio PLAT221_ALERT_4_C Large Solvent/Anion Cl Ueq(max)/Ueq(min) ... 3.02 Ratio PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C22 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.09 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.86 PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 43.00 Perc. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C19 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Cl1 .. 3.57 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 42.30 Deg. O1 -C3 -O1' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 28.40 Deg. CL1' -C22 -CL1 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 18.00 Deg. CL3' -C22 -CL3 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 27.50 Deg. CL2' -C22 -CL2 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.50 From the CIF: _reflns_number_total 4527 Count of symmetry unique reflns 2582 Completeness (_total/calc) 175.33% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1945 Fraction of Friedel pairs measured 0.753 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

17-acetyl-16-bromo-17-hydroxy-10,13-dimethyl-1,6,7,8,9,10,12,13,14, 15,16,17-dodecahydro-2H-cyclopenta[a]phenanthrene-3,11-dione chloroform solvate top
Crystal data top
C21H27BrO4·CHCl3Dx = 1.480 Mg m3
Mr = 542.70Melting point: 472.2 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 16366 reflections
a = 10.443 (2) Åθ = 3.3–27.5°
b = 12.324 (3) ŵ = 2.04 mm1
c = 18.927 (4) ÅT = 296 K
V = 2435.9 (9) Å3Plate, colorless
Z = 40.23 × 0.18 × 0.05 mm
F(000) = 1112
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer
4527 independent reflections
Radiation source: fine-focus sealed tube3310 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.082
φ? ω? scansθmax = 25.5°, θmin = 3.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1211
Tmin = 0.648, Tmax = 0.901k = 1414
20190 measured reflectionsl = 2222
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.0364P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.091(Δ/σ)max = 0.001
S = 0.95Δρmax = 0.27 e Å3
4527 reflectionsΔρmin = 0.30 e Å3
309 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
6 restraintsExtinction coefficient: 0.0070 (11)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with 1972 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.01 (1)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Br10.01979 (5)0.98165 (4)0.191311 (19)0.07040 (19)
Cl10.0126 (7)0.4280 (8)0.1234 (4)0.136 (3)0.488 (9)
Cl20.1017 (4)0.2558 (4)0.1122 (2)0.0847 (15)0.488 (9)
Cl30.1541 (6)0.2742 (9)0.0629 (6)0.115 (3)0.488 (9)
Cl1'0.0059 (6)0.4614 (3)0.0857 (4)0.0987 (18)0.512 (9)
Cl2'0.1164 (6)0.2499 (5)0.0692 (9)0.256 (5)0.512 (9)
Cl3'0.1411 (9)0.2707 (9)0.0350 (6)0.152 (4)0.512 (9)
C10.0966 (4)0.8674 (4)0.26704 (17)0.0603 (12)
H1A0.18580.84910.25930.072*
H1B0.04630.80210.25990.072*
C20.0797 (4)0.9057 (5)0.34310 (19)0.0697 (14)
H2A0.13720.96600.35220.084*
H2B0.10180.84730.37520.084*
C30.0539 (5)0.9403 (6)0.3562 (2)0.108 (2)
C40.1211 (4)0.9909 (5)0.29772 (19)0.0863 (16)
H4A0.20281.01810.30600.104*
C50.0729 (3)1.0008 (4)0.23266 (17)0.0535 (11)
C60.1443 (4)1.0646 (4)0.17798 (19)0.0642 (12)
H6A0.23011.07910.19510.077*
H6B0.10181.13390.17130.077*
C70.1531 (3)1.0065 (3)0.10701 (16)0.0485 (9)
H7A0.18941.05550.07220.058*
H7B0.21000.94470.11140.058*
C80.0225 (3)0.9679 (3)0.08164 (15)0.0370 (7)
H8A0.03211.03140.07360.044*
C90.0406 (3)0.8955 (3)0.13884 (15)0.0348 (8)
H9A0.02100.83690.14720.042*
C100.0554 (3)0.9534 (3)0.21207 (16)0.0433 (9)
C110.1600 (3)0.8392 (3)0.11102 (15)0.0399 (8)
C120.1470 (3)0.7815 (3)0.04081 (15)0.0373 (8)
H12A0.22960.75370.02590.045*
H12B0.08840.72080.04540.045*
C130.0958 (3)0.8622 (3)0.01417 (15)0.0333 (8)
C140.0329 (3)0.9039 (3)0.01293 (14)0.0331 (7)
H14A0.08650.84030.02250.040*
C150.0904 (4)0.9619 (3)0.05090 (16)0.0460 (9)
H15A0.18300.96440.04780.055*
H15B0.05761.03530.05490.055*
C160.0468 (4)0.8918 (3)0.11386 (15)0.0428 (9)
H16A0.12130.85180.13150.051*
C170.0509 (3)0.8087 (3)0.08501 (15)0.0357 (8)
C180.1547 (4)0.7726 (3)0.13801 (16)0.0418 (9)
C190.1094 (4)0.7143 (4)0.20317 (18)0.0636 (12)
H19A0.18160.69620.23220.095*
H19B0.06540.64900.18970.095*
H19C0.05210.76030.22920.095*
C200.1536 (4)1.0461 (4)0.2089 (2)0.0685 (13)
H20A0.12711.09830.17430.103*
H20B0.15921.08040.25430.103*
H20C0.23591.01740.19610.103*
C210.1945 (4)0.9521 (3)0.02571 (17)0.0449 (9)
H21A0.21930.98190.01910.067*
H21B0.26840.92260.04900.067*
H21C0.15781.00820.05450.067*
C220.0018 (4)0.3354 (3)0.0564 (2)0.0810 (15)
H22A0.03170.35010.00900.097*
O10.0875 (16)0.9716 (15)0.4182 (6)0.127 (6)0.488 (9)
O1'0.1131 (13)0.9001 (12)0.4106 (6)0.098 (4)0.512 (9)
O20.2625 (2)0.8404 (2)0.14253 (11)0.0547 (7)
O30.0139 (2)0.71145 (18)0.06626 (10)0.0445 (6)
H3A0.07720.70400.09140.067*
O40.2681 (3)0.7823 (2)0.12630 (13)0.0594 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0798 (3)0.0796 (3)0.0518 (2)0.0131 (2)0.0065 (2)0.0256 (2)
Cl10.105 (4)0.164 (6)0.138 (4)0.014 (4)0.025 (4)0.080 (4)
Cl20.067 (3)0.061 (2)0.126 (3)0.0094 (17)0.024 (2)0.0188 (18)
Cl30.055 (3)0.095 (4)0.196 (8)0.012 (2)0.021 (3)0.054 (5)
Cl1'0.080 (3)0.0490 (18)0.168 (4)0.0156 (16)0.026 (3)0.020 (2)
Cl2'0.094 (4)0.089 (4)0.585 (16)0.003 (3)0.108 (7)0.081 (7)
Cl3'0.180 (7)0.082 (4)0.196 (8)0.016 (4)0.098 (6)0.018 (4)
C10.054 (3)0.090 (3)0.0372 (18)0.013 (2)0.0035 (17)0.002 (2)
C20.049 (3)0.116 (4)0.044 (2)0.018 (3)0.0055 (18)0.012 (2)
C30.067 (4)0.215 (7)0.041 (2)0.053 (4)0.003 (2)0.007 (3)
C40.053 (3)0.153 (5)0.054 (2)0.035 (3)0.0008 (18)0.018 (3)
C50.034 (2)0.078 (3)0.0479 (18)0.009 (2)0.0030 (14)0.021 (2)
C60.053 (3)0.075 (3)0.065 (3)0.024 (2)0.001 (2)0.017 (2)
C70.040 (2)0.058 (3)0.0477 (17)0.017 (2)0.0009 (14)0.0023 (18)
C80.0284 (19)0.0391 (19)0.0436 (15)0.0050 (17)0.0011 (13)0.0017 (14)
C90.026 (2)0.042 (2)0.0367 (15)0.0004 (16)0.0004 (13)0.0059 (13)
C100.030 (2)0.057 (3)0.0423 (17)0.0057 (17)0.0001 (13)0.0133 (15)
C110.037 (2)0.047 (2)0.0353 (16)0.0077 (18)0.0013 (14)0.0017 (15)
C120.031 (2)0.040 (2)0.0402 (16)0.0082 (17)0.0026 (14)0.0040 (15)
C130.0287 (19)0.037 (2)0.0344 (16)0.0018 (16)0.0022 (13)0.0008 (13)
C140.0246 (18)0.0366 (19)0.0382 (15)0.0016 (17)0.0001 (13)0.0001 (13)
C150.040 (2)0.048 (2)0.0498 (18)0.0102 (19)0.0047 (15)0.0020 (17)
C160.037 (2)0.052 (2)0.0399 (17)0.0026 (18)0.0036 (15)0.0040 (15)
C170.030 (2)0.040 (2)0.0371 (15)0.0016 (16)0.0011 (13)0.0031 (14)
C180.040 (3)0.046 (2)0.0393 (17)0.0015 (18)0.0022 (16)0.0008 (16)
C190.062 (3)0.084 (3)0.044 (2)0.004 (2)0.0071 (18)0.019 (2)
C200.058 (3)0.082 (4)0.065 (3)0.015 (2)0.003 (2)0.026 (2)
C210.037 (2)0.048 (2)0.0495 (18)0.0101 (18)0.0036 (15)0.0058 (16)
C220.095 (5)0.071 (3)0.077 (3)0.010 (3)0.007 (3)0.008 (2)
O10.107 (11)0.234 (18)0.040 (4)0.080 (12)0.011 (5)0.020 (9)
O1'0.053 (5)0.190 (14)0.050 (5)0.002 (8)0.014 (4)0.004 (7)
O20.0292 (15)0.090 (2)0.0452 (13)0.0170 (14)0.0075 (10)0.0147 (13)
O30.0430 (17)0.0440 (14)0.0466 (12)0.0101 (12)0.0107 (11)0.0007 (9)
O40.0338 (17)0.083 (2)0.0613 (14)0.0054 (15)0.0018 (13)0.0167 (14)
Geometric parameters (Å, º) top
Br1—C161.964 (3)C9—H9A0.9800
Cl1—C221.709 (6)C10—C201.536 (5)
Cl2—C221.802 (5)C11—O21.225 (4)
Cl3—C221.765 (7)C11—C121.514 (4)
Cl1'—C221.650 (5)C12—C131.536 (4)
Cl2'—C221.641 (7)C12—H12A0.9700
Cl3'—C221.708 (8)C12—H12B0.9700
C1—C21.525 (5)C13—C141.528 (4)
C1—C101.546 (5)C13—C211.528 (5)
C1—H1A0.9700C13—C171.566 (4)
C1—H1B0.9700C14—C151.527 (4)
C2—C31.480 (6)C14—H14A0.9800
C2—H2A0.9700C15—C161.540 (5)
C2—H2B0.9700C15—H15A0.9700
C3—O11.285 (12)C15—H15B0.9700
C3—O1'1.299 (14)C16—C171.545 (5)
C3—C41.452 (6)C16—H16A0.9800
C4—C51.336 (5)C17—O31.421 (4)
C4—H4A0.9300C17—C181.542 (5)
C5—C61.499 (5)C18—O41.211 (4)
C5—C101.512 (5)C18—C191.504 (5)
C6—C71.525 (5)C19—H19A0.9600
C6—H6A0.9700C19—H19B0.9600
C6—H6B0.9700C19—H19C0.9600
C7—C81.522 (4)C20—H20A0.9600
C7—H7A0.9700C20—H20B0.9600
C7—H7B0.9700C20—H20C0.9600
C8—C141.525 (4)C21—H21A0.9600
C8—C91.550 (4)C21—H21B0.9600
C8—H8A0.9800C21—H21C0.9600
C9—C111.521 (5)C22—H22A0.9800
C9—C101.567 (4)O3—H3A0.8200
C2—C1—C10113.0 (4)C12—C13—C17114.3 (3)
C2—C1—H1A109.0C8—C14—C15117.4 (3)
C10—C1—H1A109.0C8—C14—C13113.4 (3)
C2—C1—H1B109.0C15—C14—C13103.7 (2)
C10—C1—H1B109.0C8—C14—H14A107.2
H1A—C1—H1B107.8C15—C14—H14A107.2
C3—C2—C1110.9 (3)C13—C14—H14A107.2
C3—C2—H2A109.5C14—C15—C16103.5 (3)
C1—C2—H2A109.5C14—C15—H15A111.1
C3—C2—H2B109.5C16—C15—H15A111.1
C1—C2—H2B109.5C14—C15—H15B111.1
H2A—C2—H2B108.1C16—C15—H15B111.1
O1—C3—O1'42.3 (8)H15A—C15—H15B109.0
O1—C3—C4115.8 (8)C15—C16—C17107.1 (2)
O1'—C3—C4122.5 (8)C15—C16—Br1111.4 (2)
O1—C3—C2119.8 (8)C17—C16—Br1113.8 (2)
O1'—C3—C2118.2 (8)C15—C16—H16A108.1
C4—C3—C2116.9 (4)C17—C16—H16A108.1
C5—C4—C3124.0 (4)Br1—C16—H16A108.1
C5—C4—H4A118.0O3—C17—C18104.7 (3)
C3—C4—H4A118.0O3—C17—C16109.5 (3)
C4—C5—C6119.8 (4)C18—C17—C16115.2 (3)
C4—C5—C10122.5 (4)O3—C17—C13106.5 (2)
C6—C5—C10117.7 (3)C18—C17—C13117.9 (3)
C5—C6—C7113.1 (3)C16—C17—C13102.8 (3)
C5—C6—H6A109.0O4—C18—C19120.3 (3)
C7—C6—H6A109.0O4—C18—C17122.7 (3)
C5—C6—H6B109.0C19—C18—C17116.7 (3)
C7—C6—H6B109.0C18—C19—H19A109.5
H6A—C6—H6B107.8C18—C19—H19B109.5
C8—C7—C6111.7 (3)H19A—C19—H19B109.5
C8—C7—H7A109.3C18—C19—H19C109.5
C6—C7—H7A109.3H19A—C19—H19C109.5
C8—C7—H7B109.3H19B—C19—H19C109.5
C6—C7—H7B109.3C10—C20—H20A109.5
H7A—C7—H7B107.9C10—C20—H20B109.5
C7—C8—C14111.6 (3)H20A—C20—H20B109.5
C7—C8—C9109.9 (2)C10—C20—H20C109.5
C14—C8—C9109.1 (3)H20A—C20—H20C109.5
C7—C8—H8A108.7H20B—C20—H20C109.5
C14—C8—H8A108.7C13—C21—H21A109.5
C9—C8—H8A108.7C13—C21—H21B109.5
C11—C9—C8111.7 (2)H21A—C21—H21B109.5
C11—C9—C10115.7 (3)C13—C21—H21C109.5
C8—C9—C10113.4 (3)H21A—C21—H21C109.5
C11—C9—H9A104.9H21B—C21—H21C109.5
C8—C9—H9A104.9Cl2'—C22—Cl1'125.1 (5)
C10—C9—H9A104.9Cl2'—C22—Cl3'112.1 (5)
C5—C10—C20108.3 (3)Cl1'—C22—Cl3'119.8 (5)
C5—C10—C1109.7 (3)Cl2'—C22—Cl1111.7 (8)
C20—C10—C1110.5 (3)Cl1'—C22—Cl128.4 (2)
C5—C10—C9108.4 (3)Cl3'—C22—Cl1115.5 (5)
C20—C10—C9111.7 (3)Cl2'—C22—Cl3113.2 (5)
C1—C10—C9108.1 (3)Cl1'—C22—Cl3110.8 (5)
O2—C11—C12120.8 (3)Cl3'—C22—Cl318.0 (6)
O2—C11—C9122.8 (3)Cl1—C22—Cl3100.0 (4)
C12—C11—C9116.4 (3)Cl2'—C22—Cl227.5 (5)
C11—C12—C13108.8 (3)Cl1'—C22—Cl2109.4 (3)
C11—C12—H12A109.9Cl3'—C22—Cl2113.3 (5)
C13—C12—H12A109.9Cl1—C22—Cl288.2 (5)
C11—C12—H12B109.9Cl3—C22—Cl2105.5 (5)
C13—C12—H12B109.9Cl2'—C22—H22A89.2
H12A—C12—H12B108.3Cl1'—C22—H22A98.2
C14—C13—C21113.4 (3)Cl3'—C22—H22A100.0
C14—C13—C12107.2 (3)Cl1—C22—H22A125.4
C21—C13—C12109.4 (3)Cl3—C22—H22A117.7
C14—C13—C1799.5 (2)Cl2—C22—H22A115.0
C21—C13—C17112.6 (2)C17—O3—H3A109.5
C10—C1—C2—C355.6 (6)C11—C12—C13—C1458.8 (4)
C1—C2—C3—O1177.5 (12)C11—C12—C13—C2164.6 (3)
C1—C2—C3—O1'128.8 (8)C11—C12—C13—C17168.0 (3)
C1—C2—C3—C433.9 (8)C7—C8—C14—C1559.6 (4)
O1—C3—C4—C5154.7 (11)C9—C8—C14—C15178.8 (3)
O1'—C3—C4—C5157.1 (9)C7—C8—C14—C13179.3 (3)
C2—C3—C4—C54.8 (10)C9—C8—C14—C1357.6 (4)
C3—C4—C5—C6173.6 (6)C21—C13—C14—C856.9 (4)
C3—C4—C5—C103.8 (8)C12—C13—C14—C863.9 (4)
C4—C5—C6—C7133.7 (4)C17—C13—C14—C8176.8 (3)
C10—C5—C6—C748.8 (6)C21—C13—C14—C1571.6 (3)
C5—C6—C7—C851.0 (5)C12—C13—C14—C15167.6 (3)
C6—C7—C8—C14176.5 (3)C17—C13—C14—C1548.3 (3)
C6—C7—C8—C955.3 (4)C8—C14—C15—C16162.1 (3)
C7—C8—C9—C11170.0 (3)C13—C14—C15—C1636.1 (3)
C14—C8—C9—C1147.4 (4)C14—C15—C16—C179.1 (4)
C7—C8—C9—C1057.1 (4)C14—C15—C16—Br1134.1 (3)
C14—C8—C9—C10179.7 (3)C15—C16—C17—O392.6 (3)
C4—C5—C10—C20103.5 (5)Br1—C16—C17—O3143.8 (2)
C6—C5—C10—C2074.0 (4)C15—C16—C17—C18149.8 (3)
C4—C5—C10—C117.3 (5)Br1—C16—C17—C1826.2 (4)
C6—C5—C10—C1165.3 (4)C15—C16—C17—C1320.3 (4)
C4—C5—C10—C9135.1 (4)Br1—C16—C17—C13103.3 (2)
C6—C5—C10—C947.5 (5)C14—C13—C17—O373.7 (3)
C2—C1—C10—C546.5 (4)C21—C13—C17—O3165.9 (3)
C2—C1—C10—C2072.9 (4)C12—C13—C17—O340.2 (4)
C2—C1—C10—C9164.6 (3)C14—C13—C17—C18169.2 (3)
C11—C9—C10—C5177.8 (3)C21—C13—C17—C1848.8 (4)
C8—C9—C10—C551.3 (4)C12—C13—C17—C1876.9 (4)
C11—C9—C10—C2062.8 (4)C14—C13—C17—C1641.4 (3)
C8—C9—C10—C2068.1 (4)C21—C13—C17—C1679.1 (3)
C11—C9—C10—C158.9 (4)C12—C13—C17—C16155.3 (3)
C8—C9—C10—C1170.1 (3)O3—C17—C18—O4116.7 (4)
C8—C9—C11—O2130.2 (4)C16—C17—C18—O4123.1 (4)
C10—C9—C11—O21.5 (5)C13—C17—C18—O41.4 (5)
C8—C9—C11—C1249.1 (4)O3—C17—C18—C1957.6 (4)
C10—C9—C11—C12179.2 (3)C16—C17—C18—C1962.6 (4)
O2—C11—C12—C13124.5 (4)C13—C17—C18—C19175.7 (3)
C9—C11—C12—C1354.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O2i0.822.012.819 (3)169
Symmetry code: (i) x1/2, y+3/2, z.
 

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