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The biologically transformed product of estradiol valerate, namely 3,7α-di­hydroxy­estra-1,3,5(10)-trien-17-one monohydrate, C18H22O3·H2O, has been investigated using UV–Vis, IR, 1H and 13C NMR spectroscopic techniques, as well as by mass spectrometric analysis. Its crystal structure was determined using single-crystal X-ray diffraction based on data collected at 100 K. The structure was refined using the independent atom model (IAM) and the transferred electron-density parameters from the ELMAM2 database. The structure is stabilized by a network of hydrogen bonds and van der Waals inter­actions. The topology of the hydrogen bonds has been analyzed by the Bader theory of `Atoms in Mol­ecules' framework. The mol­ecular electrostatic potential for the transferred multipolar atom model reveals an asymmetric character of the charge distribution across the mol­ecule due to a substantial charge delocalization within the mol­ecule. The mol­ecular dipole moment was also calculated, which shows that the mol­ecule has a strongly polar character.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618004953/ly3062sup1.cif
Contains datablocks IAM_SHELXL, IAM_MoPro, ELMAM2_MoPro, New_Global_Publ_Block

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004953/ly3062IAM_SHELXLsup2.hkl
Contains datablock IAM_SHELXL

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004953/ly3062ELMAM2_MoProsup3.hkl
Contains datablock ELMAM2_MoPro

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618004953/ly3062sup4.pdf
Topological properties at the critical points of O...H and C...H intermolecular interactions in the crystal packing of compound (2) for the ELMAM2 model

CCDC references: 1832913; 1832912; 1832911

Computing details top

For all structures, data collection: Bruker D8 Venture PHOTON II Detector; cell refinement: APEX2 (Bruker, 2014); data reduction: SAINT (Bruker, 2014). Program(s) used to solve structure: SIR92 (Altomare et al., 1993) in WinGX (Farrugia, 2012) for IAM_SHELXL; SIR92 (Altomare et al., 1993) for IAM_MoPro, ELMAM2_MoPro. Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) for IAM_SHELXL; MoPro (Jelsch et al., 2005) for IAM_MoPro, ELMAM2_MoPro. Molecular graphics: Mercury (Macrae et al., 2008) for IAM_SHELXL; Mercury (Macrae et al., 2008) and MoProViewer (Guillot, 2011) for IAM_MoPro, ELMAM2_MoPro. Software used to prepare material for publication: publCIF (Westrip, 2010) for IAM_SHELXL, IAM_MoPro; pubCIF (Westrip, 2010) for ELMAM2_MoPro.

3,7α-Dihydroxyestra-1,3,5(10)-trien-17-one monohydrate (IAM_SHELXL) top
Crystal data top
C18H22O3·H2OF(000) = 328
Mr = 304.37Dx = 1.314 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
a = 6.143 (3) ÅCell parameters from 2931 reflections
b = 8.4833 (17) Åθ = 3.0–72.2°
c = 14.767 (3) ŵ = 0.74 mm1
β = 91.94 (2)°T = 100 K
V = 769.2 (4) Å3Block, colorless
Z = 20.46 × 0.22 × 0.12 mm
Data collection top
Bruker D8 Venture PHOTON II Detector
diffractometer
2905 reflections with I > 2σ(I)
Radiation source: MicrofocusRint = 0.043
ω and phi scanθmax = 72.2°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 77
Tmin = 0.727, Tmax = 0.916k = 1010
9196 measured reflectionsl = 1818
2931 independent reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.0682P)2 + 0.209P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.111(Δ/σ)max < 0.001
S = 1.10Δρmax = 0.34 e Å3
2931 reflectionsΔρmin = 0.27 e Å3
216 parametersAbsolute structure: Flack x determined using 1292 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.01 (7)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6688 (3)0.5239 (2)0.69523 (11)0.0141 (4)
H1A0.774 (6)0.490 (5)0.730 (2)0.030 (9)*
O20.6550 (3)0.7883 (2)0.27748 (12)0.0148 (4)
H2A0.574 (6)0.870 (6)0.289 (3)0.033 (10)*
O1W0.9626 (3)0.3746 (3)0.80166 (12)0.0201 (4)
H1W0.981 (6)0.370 (5)0.856 (3)0.027 (9)*
H2W1.078 (7)0.343 (5)0.783 (3)0.028 (9)*
O31.0195 (3)0.3311 (3)0.01042 (12)0.0231 (5)
C10.9590 (4)0.4364 (3)0.48721 (16)0.0124 (5)
H11.09020.38800.46930.015*
C20.9183 (4)0.4486 (3)0.57874 (16)0.0136 (5)
H21.02140.41020.62280.016*
C30.7254 (4)0.5174 (3)0.60558 (16)0.0125 (5)
C40.5790 (4)0.5774 (3)0.54083 (16)0.0131 (5)
H40.44940.62710.55940.016*
C50.6200 (4)0.5654 (3)0.44851 (16)0.0118 (5)
C60.4464 (4)0.6267 (3)0.38191 (16)0.0128 (5)
H6A0.39330.72940.40410.015*
H6B0.32190.55260.38060.015*
C70.5227 (4)0.6481 (3)0.28548 (16)0.0116 (5)
H70.39220.65760.24350.014*
C80.6552 (4)0.5052 (3)0.25817 (15)0.0110 (5)
H80.56230.40960.26560.013*
C90.8621 (4)0.4845 (3)0.31968 (15)0.0104 (5)
H90.96040.57520.30670.013*
C100.8115 (4)0.4937 (3)0.42027 (15)0.0108 (5)
C110.9846 (4)0.3337 (3)0.29445 (15)0.0129 (5)
H11A0.89340.24110.30820.015*
H11B1.12030.32630.33230.015*
C121.0424 (4)0.3285 (3)0.19371 (15)0.0131 (5)
H12A1.15050.41160.18130.016*
H12B1.10810.22510.17970.016*
C130.8380 (4)0.3538 (3)0.13362 (15)0.0128 (5)
C140.7266 (4)0.5091 (3)0.15995 (15)0.0113 (5)
H140.84090.59270.15720.014*
C150.5634 (4)0.5425 (3)0.08079 (15)0.0150 (5)
H15A0.52230.65530.07830.018*
H15B0.43020.47760.08540.018*
C160.6951 (4)0.4945 (3)0.00233 (15)0.0145 (5)
H16A0.60020.44040.04810.017*
H16B0.75980.58860.03060.017*
C170.8726 (4)0.3840 (3)0.03380 (16)0.0144 (5)
C180.6847 (4)0.2096 (3)0.13510 (17)0.0169 (5)
H18A0.55250.23190.09830.025*
H18B0.64550.18760.19760.025*
H18C0.75880.11770.11030.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0172 (8)0.0134 (9)0.0116 (8)0.0012 (7)0.0026 (6)0.0006 (6)
O20.0149 (8)0.0080 (9)0.0215 (8)0.0008 (7)0.0007 (6)0.0014 (7)
O1W0.0199 (9)0.0266 (11)0.0137 (9)0.0079 (8)0.0012 (7)0.0011 (8)
O30.0279 (10)0.0280 (11)0.0134 (8)0.0139 (8)0.0013 (7)0.0012 (8)
C10.0111 (10)0.0088 (11)0.0170 (11)0.0002 (9)0.0033 (8)0.0004 (9)
C20.0145 (10)0.0109 (11)0.0151 (11)0.0012 (9)0.0049 (8)0.0015 (9)
C30.0176 (11)0.0062 (11)0.0134 (10)0.0044 (9)0.0024 (8)0.0008 (9)
C40.0144 (11)0.0085 (11)0.0164 (11)0.0001 (9)0.0016 (8)0.0018 (9)
C50.0124 (10)0.0066 (11)0.0162 (11)0.0015 (9)0.0037 (8)0.0001 (9)
C60.0111 (10)0.0126 (12)0.0144 (11)0.0022 (9)0.0017 (8)0.0015 (9)
C70.0107 (10)0.0093 (11)0.0146 (11)0.0001 (9)0.0027 (8)0.0017 (9)
C80.0111 (10)0.0100 (11)0.0116 (10)0.0000 (9)0.0045 (8)0.0006 (9)
C90.0108 (10)0.0092 (11)0.0112 (10)0.0016 (9)0.0034 (8)0.0011 (8)
C100.0129 (10)0.0077 (10)0.0116 (10)0.0010 (9)0.0021 (8)0.0006 (9)
C110.0157 (11)0.0111 (11)0.0117 (10)0.0027 (9)0.0033 (8)0.0003 (9)
C120.0163 (11)0.0105 (12)0.0124 (10)0.0043 (9)0.0014 (8)0.0003 (9)
C130.0157 (11)0.0110 (12)0.0114 (10)0.0009 (9)0.0038 (8)0.0008 (9)
C140.0121 (10)0.0088 (11)0.0125 (11)0.0011 (9)0.0048 (8)0.0003 (9)
C150.0163 (11)0.0160 (12)0.0125 (10)0.0052 (9)0.0041 (9)0.0024 (9)
C160.0166 (11)0.0142 (11)0.0123 (10)0.0028 (10)0.0044 (8)0.0010 (9)
C170.0194 (11)0.0099 (11)0.0134 (11)0.0017 (10)0.0049 (8)0.0002 (9)
C180.0239 (13)0.0100 (11)0.0166 (11)0.0019 (10)0.0049 (9)0.0014 (9)
Geometric parameters (Å, º) top
O1—C31.381 (3)C8—H81.0000
O1—H1A0.87 (4)C9—C101.530 (3)
O2—C71.447 (3)C9—C111.536 (3)
O2—H2A0.87 (5)C9—H91.0000
O1W—O1W0.000 (6)C11—C121.542 (3)
O1W—H1W0.81 (4)C11—H11A0.9900
O1W—H2W0.81 (4)C11—H11B0.9900
O3—C171.217 (3)C12—C131.528 (3)
C1—C21.387 (3)C12—H12A0.9900
C1—C101.405 (3)C12—H12B0.9900
C1—H10.9500C13—C171.518 (3)
C2—C31.391 (4)C13—C141.540 (3)
C2—H20.9500C13—C181.544 (3)
C3—C41.387 (3)C14—C151.541 (3)
C4—C51.398 (3)C14—H141.0000
C4—H40.9500C15—C161.547 (3)
C5—C101.401 (3)C15—H15A0.9900
C5—C61.518 (3)C15—H15B0.9900
C6—C71.525 (3)C16—C171.521 (3)
C6—H6A0.9900C16—H16A0.9900
C6—H6B0.9900C16—H16B0.9900
C7—C81.523 (3)C18—H18A0.9800
C7—H71.0000C18—H18B0.9800
C8—C141.530 (3)C18—H18C0.9800
C8—C91.547 (3)
C3—O1—H1A111 (2)C1—C10—C9121.2 (2)
C7—O2—H2A108 (3)C9—C11—C12112.87 (18)
O1W—O1W—H1W0 (10)C9—C11—H11A109.0
O1W—O1W—H2W0 (10)C12—C11—H11A109.0
H1W—O1W—H2W103 (4)C9—C11—H11B109.0
C2—C1—C10121.8 (2)C12—C11—H11B109.0
C2—C1—H1119.1H11A—C11—H11B107.8
C10—C1—H1119.1C13—C12—C11110.15 (18)
C1—C2—C3119.5 (2)C13—C12—H12A109.6
C1—C2—H2120.2C11—C12—H12A109.6
C3—C2—H2120.2C13—C12—H12B109.6
O1—C3—C4117.9 (2)C11—C12—H12B109.6
O1—C3—C2122.3 (2)H12A—C12—H12B108.1
C4—C3—C2119.8 (2)C17—C13—C12116.61 (19)
C3—C4—C5120.7 (2)C17—C13—C14100.30 (19)
C3—C4—H4119.6C12—C13—C14109.68 (19)
C5—C4—H4119.6C17—C13—C18104.66 (18)
C4—C5—C10120.17 (19)C12—C13—C18111.7 (2)
C4—C5—C6117.5 (2)C14—C13—C18113.43 (19)
C10—C5—C6122.3 (2)C8—C14—C13111.41 (18)
C5—C6—C7114.50 (19)C8—C14—C15121.54 (18)
C5—C6—H6A108.6C13—C14—C15104.42 (19)
C7—C6—H6A108.6C8—C14—H14106.2
C5—C6—H6B108.6C13—C14—H14106.2
C7—C6—H6B108.6C15—C14—H14106.2
H6A—C6—H6B107.6C14—C15—C16102.07 (18)
O2—C7—C8109.01 (18)C14—C15—H15A111.4
O2—C7—C6111.41 (19)C16—C15—H15A111.4
C8—C7—C6109.67 (19)C14—C15—H15B111.4
O2—C7—H7108.9C16—C15—H15B111.4
C8—C7—H7108.9H15A—C15—H15B109.2
C6—C7—H7108.9C17—C16—C15105.76 (19)
C7—C8—C14114.03 (18)C17—C16—H16A110.6
C7—C8—C9111.77 (18)C15—C16—H16A110.6
C14—C8—C9107.62 (17)C17—C16—H16B110.6
C7—C8—H8107.7C15—C16—H16B110.6
C14—C8—H8107.7H16A—C16—H16B108.7
C9—C8—H8107.7O3—C17—C13126.1 (2)
C10—C9—C11113.27 (17)O3—C17—C16125.1 (2)
C10—C9—C8111.99 (18)C13—C17—C16108.8 (2)
C11—C9—C8110.57 (18)C13—C18—H18A109.5
C10—C9—H9106.9C13—C18—H18B109.5
C11—C9—H9106.9H18A—C18—H18B109.5
C8—C9—H9106.9C13—C18—H18C109.5
C5—C10—C1118.0 (2)H18A—C18—H18C109.5
C5—C10—C9120.76 (19)H18B—C18—H18C109.5
C10—C1—C2—C30.8 (4)C8—C9—C10—C1162.4 (2)
C1—C2—C3—O1175.8 (2)C10—C9—C11—C12177.84 (17)
C1—C2—C3—C41.9 (4)C8—C9—C11—C1255.5 (2)
O1—C3—C4—C5175.9 (2)C9—C11—C12—C1353.9 (3)
C2—C3—C4—C51.9 (4)C11—C12—C13—C17168.4 (2)
C3—C4—C5—C100.7 (3)C11—C12—C13—C1455.3 (3)
C3—C4—C5—C6177.1 (2)C11—C12—C13—C1871.4 (3)
C4—C5—C6—C7165.5 (2)C7—C8—C14—C13173.83 (18)
C10—C5—C6—C716.8 (3)C9—C8—C14—C1361.6 (2)
C5—C6—C7—O276.3 (3)C7—C8—C14—C1550.2 (3)
C5—C6—C7—C844.5 (3)C9—C8—C14—C15174.7 (2)
O2—C7—C8—C1461.8 (2)C17—C13—C14—C8175.36 (17)
C6—C7—C8—C14175.94 (18)C12—C13—C14—C861.4 (2)
O2—C7—C8—C960.5 (2)C18—C13—C14—C864.3 (2)
C6—C7—C8—C961.7 (2)C17—C13—C14—C1542.4 (2)
C7—C8—C9—C1049.0 (3)C12—C13—C14—C15165.7 (2)
C14—C8—C9—C10174.96 (19)C18—C13—C14—C1568.6 (2)
C7—C8—C9—C11176.37 (18)C8—C14—C15—C16166.9 (2)
C14—C8—C9—C1157.7 (2)C13—C14—C15—C1640.0 (2)
C4—C5—C10—C10.5 (3)C14—C15—C16—C1721.3 (3)
C6—C5—C10—C1178.1 (2)C12—C13—C17—O331.8 (4)
C4—C5—C10—C9178.0 (2)C14—C13—C17—O3150.0 (3)
C6—C5—C10—C94.4 (3)C18—C13—C17—O392.2 (3)
C2—C1—C10—C50.4 (3)C12—C13—C17—C16147.2 (2)
C2—C1—C10—C9177.9 (2)C14—C13—C17—C1628.9 (2)
C11—C9—C10—C5146.1 (2)C18—C13—C17—C1688.8 (2)
C8—C9—C10—C520.2 (3)C15—C16—C17—O3174.0 (2)
C11—C9—C10—C136.5 (3)C15—C16—C17—C134.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O1W0.87 (4)1.82 (4)2.672 (3)167 (4)
O2—H2A···O1i0.87 (5)2.00 (5)2.858 (3)166 (4)
O1W—H1W···O3ii0.81 (4)2.00 (4)2.809 (3)173 (4)
O1W—H2W···O2iii0.81 (4)1.95 (4)2.758 (3)171 (4)
C16—H16B···O3iv0.992.533.353 (3)141
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x, y, z+1; (iii) x+2, y1/2, z+1; (iv) x+2, y+1/2, z.
3,7α-Dihydroxyestra-1,3,5(10)-trien-17-one monohydrate (IAM_MoPro) top
Crystal data top
C18H22O3·H2OF(000) = 328
Mr = 304.37Dx = 1.315 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ybCell parameters from 2931 reflections
a = 6.143 (3) Åθ = 3.0–72.2°
b = 8.4833 (17) ŵ = 0.74 mm1
c = 14.767 (3) ÅT = 100 K
β = 91.94 (2)°Block, colorless
V = 769.2 (4) Å30.46 × 0.22 × 0.12 mm
Z = 2
Data collection top
Bruker D8 Venture PHOTON II Detector
diffractometer
2931 independent reflections
Radiation source: Microfocus2905 reflections with > 2.0σ(I)
Graphite monochromatorRint = 0.043
ω and phi scanθmax = 72.2°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 07
Tmin = 0.727, Tmax = 0.916k = 1010
9196 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: difference Fourier map
wR(F2) = 0.134Only H-atom coordinates refined
S = 1.70 w = 1/[σ2(Fo2) + (0.06P)2 + 0.05P]
where P = (Fo2 + 2Fc2)/3
2931 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.47 e Å3
Special details top

Refinement. Refinement of F2 against reflections. The threshold expression of F2 > σ(F2) is used for calculating R-factors(gt) 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*/Ueq
O10.6691 (2)0.5303 (18)0.69523 (9)0.0145 (2)
H1A0.771 (7)0.497 (6)0.729 (3)0.02703
O20.6550 (2)0.7949 (18)0.27754 (9)0.0150 (2)
H2A0.569 (7)0.878 (6)0.287 (3)0.02693
O1W0.9627 (2)0.3808 (18)0.80172 (10)0.0210 (3)
H1W0.981 (7)0.383 (7)0.857 (3)0.03779
H2W1.089 (7)0.352 (6)0.778 (3)0.03638
O31.0190 (3)0.3374 (18)0.01060 (10)0.0237 (3)
C10.9593 (3)0.4431 (18)0.48726 (13)0.0131 (3)
H11.108 (17)0.387 (5)0.467 (2)0.02779
C20.9186 (3)0.4551 (18)0.57883 (13)0.0142 (3)
H21.036 (5)0.411 (5)0.629 (17)0.02932
C30.7256 (3)0.5237 (18)0.60563 (13)0.0126 (3)
C40.5789 (3)0.5840 (18)0.54091 (13)0.0133 (3)
H40.431 (17)0.640 (5)0.562 (3)0.02804
C50.6200 (3)0.5721 (18)0.44843 (13)0.0122 (3)
C60.4462 (3)0.6331 (18)0.38198 (13)0.0136 (3)
H6A0.387 (6)0.746 (17)0.407 (2)0.02937
H6B0.309 (5)0.551 (17)0.381 (3)0.02862
C70.5231 (3)0.6547 (19)0.28560 (13)0.0120 (3)
H70.380 (4)0.665 (6)0.239 (17)0.02545
C80.6548 (3)0.5115 (18)0.25829 (12)0.0111 (3)
H80.553 (5)0.406 (17)0.266 (3)0.02337
C90.8624 (3)0.4910 (18)0.31962 (12)0.0108 (3)
H90.971 (5)0.590 (17)0.305 (3)0.02281
C100.8115 (3)0.5000 (19)0.42027 (12)0.0111 (3)
C110.9845 (3)0.3399 (18)0.29438 (12)0.0135 (3)
H11A0.884 (6)0.238 (17)0.310 (3)0.02872
H11B1.134 (3)0.331 (6)0.336 (17)0.02925
C121.0428 (3)0.3350 (18)0.19373 (12)0.0136 (3)
H12A1.162 (5)0.426 (17)0.180 (3)0.03017
H12B1.115 (7)0.221 (17)0.178 (3)0.03286
C130.8378 (3)0.3600 (18)0.13353 (12)0.0136 (3)
C140.7264 (3)0.5152 (19)0.15996 (12)0.0115 (3)
H140.852 (5)0.607 (17)0.157 (3)0.02364
C150.5631 (3)0.5489 (18)0.08092 (12)0.0155 (3)
H15A0.518 (7)0.673 (17)0.078 (3)0.03038
H15B0.417 (17)0.477 (5)0.086 (3)0.03153
C160.6949 (3)0.5010 (18)0.00233 (12)0.0153 (3)
H16A0.591 (6)0.441 (5)0.053 (17)0.03449
H16B0.767 (6)0.604 (17)0.034 (3)0.03202
C170.8725 (3)0.3904 (18)0.03395 (13)0.0146 (3)
C180.6848 (3)0.2162 (18)0.13490 (13)0.0177 (3)
H18A0.539 (4)0.240 (6)0.094 (17)0.03948
H18B0.642 (8)0.191 (6)0.204 (17)0.03737
H18C0.766 (7)0.115 (17)0.108 (3)0.04153
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0176 (6)0.0141 (7)0.0117 (6)0.0003 (5)0.0019 (5)0.0012 (5)
H1A0.027060.031360.022330.004510.004300.00016
O20.0144 (6)0.0091 (7)0.0216 (7)0.0011 (5)0.0009 (5)0.0012 (5)
H2A0.031050.015440.034460.005480.003260.00141
O1W0.0208 (7)0.0274 (9)0.0147 (7)0.0072 (6)0.0016 (5)0.0022 (6)
H1W0.043950.050820.018210.006670.004680.00094
H2W0.029780.047800.031550.010470.001110.00082
O30.0293 (8)0.0280 (9)0.0137 (6)0.0140 (7)0.0012 (5)0.0002 (6)
C10.0124 (8)0.0096 (9)0.0170 (9)0.0006 (7)0.0042 (6)0.0007 (7)
H10.021970.034140.027170.008880.000370.00007
C20.0153 (8)0.0113 (9)0.0156 (9)0.0012 (7)0.0043 (6)0.0014 (7)
H20.026750.037480.023140.006920.007650.00240
C30.0174 (8)0.0058 (9)0.0144 (8)0.0052 (7)0.0029 (6)0.0000 (7)
C40.0151 (8)0.0086 (8)0.0161 (9)0.0005 (7)0.0023 (6)0.0020 (7)
H40.024740.030530.028960.008640.002370.00087
C50.0126 (8)0.0072 (9)0.0167 (8)0.0010 (7)0.0031 (6)0.0000 (7)
C60.0125 (8)0.0142 (10)0.0139 (8)0.0020 (7)0.0016 (6)0.0024 (7)
H6A0.036670.020740.030650.009160.000470.00151
H6B0.023160.030430.031960.009170.003590.00363
C70.0115 (8)0.0091 (9)0.0151 (8)0.0004 (7)0.0022 (6)0.0021 (7)
H70.020210.029120.026520.003010.006760.00291
C80.0109 (8)0.0108 (8)0.0114 (8)0.0008 (7)0.0046 (6)0.0001 (7)
H80.024300.016890.028680.007390.002880.00072
C90.0103 (7)0.0104 (9)0.0115 (8)0.0017 (7)0.0036 (6)0.0003 (7)
H90.021670.017780.028860.006320.000970.00246
C100.0135 (8)0.0085 (8)0.0112 (8)0.0001 (7)0.0024 (6)0.0007 (7)
C110.0167 (8)0.0126 (9)0.0110 (8)0.0032 (7)0.0030 (6)0.0000 (7)
H11A0.036550.017670.032040.003780.002870.00013
H11B0.024600.035680.026910.007790.007500.00081
C120.0175 (9)0.0114 (9)0.0119 (8)0.0046 (7)0.0014 (6)0.0003 (7)
H12A0.029070.031780.029480.002800.001500.00574
H12B0.044320.025120.028940.016630.002010.00150
C130.0163 (9)0.0115 (10)0.0127 (8)0.0010 (7)0.0041 (6)0.0007 (7)
C140.0126 (8)0.0094 (9)0.0123 (8)0.0016 (7)0.0047 (6)0.0002 (7)
H140.021920.019800.029050.003770.001340.00257
C150.0166 (8)0.0182 (10)0.0113 (8)0.0051 (7)0.0039 (6)0.0027 (7)
H15A0.036650.023930.030290.008820.002790.00352
H15B0.026360.037970.029900.008550.004360.00059
C160.0173 (8)0.0152 (9)0.0131 (8)0.0030 (8)0.0038 (6)0.0002 (8)
H16A0.033920.040410.028380.003030.009940.00706
H16B0.033170.029010.034050.004540.003530.00855
C170.0199 (9)0.0099 (9)0.0138 (9)0.0011 (8)0.0050 (6)0.0004 (7)
C180.0238 (10)0.0115 (9)0.0173 (9)0.0027 (8)0.0054 (7)0.0009 (7)
H18A0.039970.035350.041820.004830.017690.00351
H18B0.055750.033690.022630.012540.000650.00135
H18C0.054430.022970.047390.004470.004740.01130
Geometric parameters (Å, º) top
O1—C31.3804 (9)C8—H81.10 (5)
O1—H1A0.84 (3)C9—C101.5311 (8)
O2—C71.4463 (9)C9—C111.5368 (10)
O2—H2A0.89 (3)C9—H91.10 (5)
O1W—H1W0.83 (3)C11—C121.5412 (8)
O1W—H2W0.89 (3)C11—H11B1.09 (6)
O3—C171.2187 (12)C11—H11A1.09 (5)
C1—C101.4057 (11)C12—C131.5317 (11)
C1—C21.3872 (10)C12—H12B1.09 (6)
C1—H11.08 (4)C12—H12A1.09 (5)
C2—C31.3900 (12)C13—C171.5151 (8)
C2—H21.08 (8)C13—C141.5404 (10)
C3—C41.3887 (11)C13—C181.5409 (10)
C4—C51.4008 (9)C14—C151.5398 (10)
C4—H41.08 (4)C14—H141.10 (5)
C5—C101.4014 (11)C15—C161.5492 (10)
C5—C61.5165 (10)C15—H15A1.09 (6)
C6—C71.5256 (9)C15—H15B1.09 (4)
C6—H6A1.09 (6)C16—C171.5224 (11)
C6—H6B1.09 (4)C16—H16A1.09 (8)
C7—C81.5214 (10)C16—H16B1.09 (5)
C7—H71.10 (7)C18—H18A1.08 (6)
C8—C141.5317 (8)C18—H18B1.08 (11)
C8—C91.5491 (10)C18—H18C1.08 (5)
C3—O1—H1A111 (12)C11—C9—H9107 (24)
C7—O2—H2A108 (12)C12—C11—H11B109 (49)
H1W—O1W—H2W108 (17)C12—C11—H11A109 (12)
C10—C1—C2121.8 (7)H11B—C11—H11A107 (24)
C10—C1—H1119 (16)C13—C12—C11110.0 (6)
C2—C1—H1119 (12)C13—C12—H12B109 (12)
C3—C2—C1119.5 (7)C13—C12—H12A110 (13)
C3—C2—H2120 (34)H12B—C12—H12A108 (33)
C4—C3—C2119.9 (7)C17—C13—C14100.3 (6)
C5—C4—H4119 (13)C17—C13—C12116.5 (6)
C10—C5—C6122.5 (7)C17—C13—C18104.7 (6)
C10—C5—C4120.1 (7)C14—C13—C12109.6 (6)
C6—C5—C4117.4 (6)C14—C13—C18113.4 (6)
C7—C6—C5114.3 (6)C15—C14—H14106 (13)
C7—C6—H6A109 (14)C16—C15—H15A111 (14)
C7—C6—H6B109 (10)C16—C15—H15B111 (14)
H6A—C6—H6B108 (31)H15A—C15—H15B110 (22)
C8—C7—C6109.6 (6)C17—C16—C15105.7 (6)
C8—C7—H7109 (24)C17—C16—H16A110 (19)
C14—C8—C9107.4 (5)C17—C16—H16B110 (18)
C14—C8—H8108 (11)H16A—C16—H16B109 (35)
C9—C8—H8108 (12)H18A—C18—H18B109 (56)
C10—C9—C11113.2 (6)H18A—C18—H18C109 (32)
C10—C9—H9107 (11)H18B—C18—H18C109 (27)
O1—C3—C4—C5175.99 (13)C8—C14—C15—H15B48 (3)
O1—C3—C4—H44 (2)C8—C9—C11—C1255.95 (13)
O1—C3—C2—C1175.82 (13)C8—C9—C11—H11B177.2 (10)
O1—C3—C2—H24 (9)C8—C9—C11—H11A66 (3)
H1A—O1—C3—C4176.2 (9)H8—C8—C14—C1354 (6)
H1A—O1—C3—C26 (3)H8—C8—C14—C1570 (3)
O2—C7—C8—C1461.66 (14)H8—C8—C14—H14169 (6)
O2—C7—C8—C960.34 (14)H8—C8—C9—C1069 (2)
O2—C7—C8—H8178.7 (4)H8—C8—C9—C1158 (6)
O2—C7—C6—C576.28 (14)H8—C8—C9—H9174 (5)
O2—C7—C6—H6A45 (6)C9—C8—C14—C1361.61 (14)
O2—C7—C6—H6B162 (5)C9—C8—C14—C15174.55 (13)
H2A—O2—C7—C8172.5 (8)C9—C8—C14—H1453 (4)
H2A—O2—C7—C666 (3)C9—C11—C12—C1354.22 (15)
H2A—O2—C7—H754 (6)C9—C11—C12—H12B175 (1)
O3—C17—C13—C14150.3 (3)C9—C11—C12—H12A67 (6)
O3—C17—C13—C1232.18 (16)H9—C9—C8—C1458 (3)
O3—C17—C13—C1891.98 (17)H9—C9—C11—C1260 (3)
O3—C17—C16—C15174.23 (12)H9—C9—C11—H11B61 (6)
O3—C17—C16—H16A66 (7)H9—C9—C11—H11A178 (6)
O3—C17—C16—H16B54 (4)C10—C9—C8—C14175.09 (13)
C1—C10—C9—C8162.51 (14)C10—C9—C11—C12177.79 (13)
C1—C10—C9—C1136.89 (16)C10—C9—C11—H11B57 (12)
C1—C10—C9—H981 (3)C10—C9—C11—H11A61 (3)
C1—C10—C5—C6178.07 (11)C11—C9—C8—C1457.82 (14)
C1—C10—C5—C40.86 (13)C11—C12—C13—C17168.36 (15)
C1—C2—C3—C42.10 (13)C11—C12—C13—C1455.42 (15)
H1—C1—C10—C93 (2)C11—C12—C13—C1871.24 (15)
H1—C1—C10—C5179.94 (19)H11A—C11—C12—C1367 (3)
H1—C1—C2—C3178.6 (3)H11A—C11—C12—H12B53 (9)
H1—C1—C2—H21 (9)H11A—C11—C12—H12A172 (7)
C2—C3—C4—C52.01 (13)H11B—C11—C12—C13175.5 (10)
C2—C3—C4—H4178.4 (4)H11B—C11—C12—H12B64 (6)
C2—C1—C10—C9177.83 (5)H11B—C11—C12—H12A55 (7)
C2—C1—C10—C50.76 (13)C12—C13—C17—C16147.1 (3)
H2—C2—C3—C4178.4 (4)C12—C13—C14—C15165.61 (14)
H2—C2—C1—C10180 (1)C12—C13—C14—H1454 (4)
C3—C4—C5—C100.51 (13)C12—C13—C18—H18A177 (1)
C3—C4—C5—C6176.84 (10)C12—C13—C18—H18B57 (7)
C3—C2—C1—C100.71 (13)C12—C13—C18—H18C62 (3)
C4—C5—C10—C9177.94 (5)H12A—C12—C13—C1747 (3)
C4—C5—C6—C7165.44 (14)H12A—C12—C13—C1466 (6)
C4—C5—C6—H6A44 (4)H12A—C12—C13—C18168 (2)
C4—C5—C6—H6B73 (2)H12B—C12—C13—C1771 (3)
H4—C4—C5—C10179.86 (11)H12B—C12—C13—C14175.9 (9)
H4—C4—C5—C63 (2)H12B—C12—C13—C1849 (6)
C5—C10—C9—C820.50 (16)C13—C17—C16—C155.03 (14)
C5—C10—C9—C11146.1 (3)C13—C17—C16—H16A115 (13)
C5—C10—C9—H996 (4)C13—C17—C16—H16B125 (5)
C5—C6—C7—C844.91 (16)C13—C14—C15—C1639.91 (19)
C5—C6—C7—H7164 (3)C13—C14—C15—H15A159 (18)
C6—C7—C8—C14175.79 (15)C13—C14—C15—H15B79 (3)
C6—C7—C8—C962.21 (13)C14—C13—C17—C1628.9 (2)
C6—C7—C8—H856 (3)C14—C13—C18—H18A53 (6)
C6—C5—C10—C94.85 (12)C14—C13—C18—H18B68 (4)
H6A—C6—C7—C8166 (2)C14—C13—C18—H18C173 (2)
H6A—C6—C7—H775 (6)C14—C15—C16—C1721.2 (2)
H6A—C6—C5—C10139 (7)C14—C15—C16—H16A141 (14)
H6B—C6—C7—C877 (6)C14—C15—C16—H16B98 (3)
H6B—C6—C7—H742 (7)H14—C14—C13—C1769 (3)
H6B—C6—C5—C10104 (5)H14—C14—C13—C18179 (2)
C7—C8—C14—C13174.06 (14)H14—C14—C15—C1672 (3)
C7—C8—C14—C1550.22 (15)H14—C14—C15—H15A47 (9)
C7—C8—C14—H1471 (6)H14—C14—C15—H15B169 (6)
C7—C8—C9—C1049.36 (15)C15—C14—C13—C1742.47 (17)
C7—C8—C9—C11176.45 (14)C15—C14—C13—C1868.59 (15)
C7—C8—C9—H967 (6)H15A—C15—C16—C17140 (9)
C7—C6—C5—C1017.27 (12)H15A—C15—C16—H16A100 (5)
H7—C7—C8—C1457 (12)H15A—C15—C16—H16B20 (12)
H7—C7—C8—C9179 (2)H15B—C15—C16—C1797 (4)
H7—C7—C8—H862 (5)H15B—C15—C16—H16A22 (10)
C8—C14—C13—C17175.43 (14)H15B—C15—C16—H16B143 (11)
C8—C14—C13—C1261.43 (13)C16—C17—C13—C1888.77 (15)
C8—C14—C13—C1864.37 (15)C17—C13—C18—H18A56 (13)
C8—C14—C15—C16166.96 (14)C17—C13—C18—H18B176 (2)
C8—C14—C15—H15A74 (2)C17—C13—C18—H18C65 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O1W0.871.822.673 (2)167
C2—H2···O1W1.082.623.354 (2)125
C8—H8···C181.102.673.106 (3)103
C18—H18A···C151.082.643.021 (3)100
O1W—H1W···O3i0.851.972.805 (2)167
O1W—H1W···C17i0.852.693.492 (2)158
O2—H2A···O1ii0.911.962.857 (2)169
O2—H2A···C3ii0.912.733.533 (3)148
C6—H6A···C2ii1.092.603.594 (3)151
C6—H6A···C3ii1.092.463.484 (3)156
O1W—H2W···O2iii0.911.852.758 (2)176
C2—H2···O2iii1.082.513.581 (3)170
C16—H16B···O3iv1.092.453.354 (3)139
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1/2, z+1; (iii) x+2, y1/2, z+1; (iv) x+2, y+1/2, z.
3,7α-Dihydroxyestra-1,3,5(10)-trien-17-one monohydrate (ELMAM2_MoPro) top
Crystal data top
C18H22O3·H2OF(000) = 328
Mr = 304.37Dx = 1.315 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ybCell parameters from 2931 reflections
a = 6.143 (3) Åθ = 3.0–72.2°
b = 8.4833 (17) ŵ = 0.74 mm1
c = 14.767 (3) ÅT = 100 K
β = 91.94 (2)°Block, colorless
V = 769.2 (4) Å30.46 × 0.22 × 0.12 mm
Z = 2
Data collection top
Bruker D8 Venture PHOTON II Detector
diffractometer
2931 independent reflections
Radiation source: Microfocus2905 reflections with > 2.0σ(I)
Graphite monochromatorRint = 0.043
ω and phi scanθmax = 72.2°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 07
Tmin = 0.727, Tmax = 0.916k = 1010
9196 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: difference Fourier map
wR(F2) = 0.088H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.06P)2 + 0.05P]
where P = (Fo2 + 2Fc2)/3
2931 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

Refinement. Refinement of F2 against reflections. The threshold expression of F2 > σ(F2) is used for calculating R-factors(gt) 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*/Ueq
O10.66934 (14)0.5271 (6)0.69518 (5)0.01249 (14)
H1A0.787280.487870.733960.02703
O20.65437 (13)0.7914 (6)0.27769 (6)0.01295 (14)
H2A0.561710.883350.290400.02693
O1W0.96343 (14)0.3775 (6)0.80181 (6)0.01836 (16)
H1W0.984850.374730.866470.03779
H2W1.100740.345390.778550.03638
O31.01932 (17)0.3342 (6)0.01049 (6)0.02196 (18)
C10.95933 (19)0.4396 (6)0.48704 (8)0.01045 (18)
H11.107900.383080.466600.02779
C20.91906 (19)0.4515 (6)0.57890 (8)0.01165 (18)
H21.035920.406380.628990.02932
C30.72546 (19)0.5206 (6)0.60582 (8)0.01016 (18)
C40.57842 (19)0.5805 (6)0.54090 (8)0.01125 (18)
H40.429720.636160.561910.02804
C50.61985 (18)0.5686 (6)0.44846 (8)0.00959 (18)
C60.44667 (18)0.6297 (6)0.38192 (8)0.01110 (18)
H6A0.387710.742650.406780.02937
H6B0.310140.547260.380750.02862
C70.52304 (18)0.6516 (6)0.28552 (8)0.00955 (18)
H70.379420.660950.239400.02545
C80.65512 (18)0.5084 (6)0.25817 (7)0.00876 (17)
H80.553870.402860.266200.02337
C90.86237 (18)0.4879 (6)0.31961 (8)0.00877 (17)
H90.971000.587090.305360.02281
C100.81158 (18)0.4968 (6)0.41997 (8)0.00865 (17)
C110.98469 (19)0.3368 (6)0.29441 (8)0.01118 (19)
H11A0.884800.234250.309580.02872
H11B1.134220.327520.336210.02925
C121.04240 (19)0.3314 (6)0.19371 (8)0.01138 (19)
H12A1.162320.422510.179800.03017
H12B1.114030.217120.178280.03286
C130.83842 (19)0.3569 (6)0.13365 (8)0.01037 (19)
C140.72626 (18)0.5124 (6)0.16002 (8)0.00954 (18)
H140.852410.603910.157020.02364
C150.5634 (2)0.5455 (6)0.08096 (8)0.01324 (19)
H15A0.518190.669950.078250.03038
H15B0.417420.473030.086060.03153
C160.69493 (19)0.4977 (6)0.00228 (8)0.01307 (19)
H16A0.590850.437150.052610.03449
H16B0.766740.600910.033800.03202
C170.8726 (2)0.3874 (6)0.03400 (8)0.0127 (2)
C180.6848 (2)0.2130 (6)0.13507 (8)0.0159 (2)
H18A0.538990.236030.094670.03948
H18B0.642030.187460.203680.03737
H18C0.765690.111310.108340.04153
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0154 (4)0.0115 (5)0.0105 (4)0.0019 (3)0.0020 (3)0.0012 (3)
H1A0.027060.031360.022330.004510.004300.00016
O20.0129 (4)0.0078 (4)0.0182 (4)0.0008 (3)0.0005 (3)0.0012 (3)
H2A0.031050.015440.034460.005480.003260.00141
O1W0.0189 (4)0.0230 (5)0.0131 (4)0.0065 (4)0.0017 (3)0.0018 (4)
H1W0.043950.050820.018210.006670.004680.00094
H2W0.029780.047800.031550.010470.001110.00082
O30.0273 (5)0.0277 (6)0.0109 (4)0.0161 (4)0.0013 (3)0.0016 (4)
C10.0102 (5)0.0108 (6)0.0101 (5)0.0025 (4)0.0034 (4)0.0001 (4)
H10.021970.034140.027170.008880.000370.00007
C20.0113 (5)0.0122 (6)0.0112 (5)0.0017 (4)0.0039 (4)0.0006 (5)
H20.026750.037480.023140.006920.007650.00240
C30.0129 (5)0.0078 (6)0.0096 (5)0.0008 (5)0.0022 (4)0.0005 (4)
C40.0124 (5)0.0092 (5)0.0120 (5)0.0019 (5)0.0021 (4)0.0008 (5)
H40.024740.030530.028960.008640.002370.00087
C50.0099 (5)0.0069 (6)0.0117 (5)0.0016 (5)0.0029 (4)0.0000 (4)
C60.0096 (5)0.0109 (6)0.0126 (5)0.0029 (4)0.0017 (4)0.0019 (4)
H6A0.036670.020740.030650.009160.000470.00151
H6B0.023160.030430.031960.009170.003590.00363
C70.0090 (5)0.0077 (6)0.0117 (5)0.0013 (5)0.0024 (4)0.0014 (4)
H70.020210.029120.026520.003010.006760.00291
C80.0088 (5)0.0084 (5)0.0088 (5)0.0011 (5)0.0042 (4)0.0001 (5)
H80.024300.016890.028680.007390.002880.00072
C90.0090 (5)0.0075 (6)0.0096 (5)0.0023 (4)0.0033 (4)0.0003 (4)
H90.021670.017780.028860.006320.000970.00246
C100.0085 (5)0.0082 (5)0.0091 (5)0.0017 (4)0.0028 (4)0.0001 (5)
C110.0146 (5)0.0089 (6)0.0098 (5)0.0039 (5)0.0038 (4)0.0008 (4)
H11A0.036550.017670.032040.003780.002870.00013
H11B0.024600.035680.026910.007790.007500.00081
C120.0134 (5)0.0102 (6)0.0103 (5)0.0041 (5)0.0027 (4)0.0003 (4)
H12A0.029070.031780.029480.002800.001500.00574
H12B0.044320.025120.028940.016630.002010.00150
C130.0130 (5)0.0078 (6)0.0100 (5)0.0019 (5)0.0039 (4)0.0005 (4)
C140.0108 (5)0.0067 (6)0.0109 (5)0.0017 (4)0.0037 (4)0.0005 (4)
H140.021920.019800.029050.003770.001340.00257
C150.0139 (5)0.0149 (6)0.0106 (5)0.0050 (5)0.0040 (4)0.0018 (4)
H15A0.036650.023930.030290.008820.002790.00352
H15B0.026360.037970.029900.008550.004360.00059
C160.0156 (5)0.0124 (6)0.0109 (5)0.0031 (5)0.0044 (4)0.0015 (5)
H16A0.033920.040410.028380.003030.009940.00706
H16B0.033170.029010.034050.004540.003530.00855
C170.0174 (6)0.0104 (6)0.0101 (5)0.0049 (5)0.0038 (4)0.0013 (5)
C180.0229 (7)0.0089 (6)0.0154 (5)0.0025 (5)0.0049 (4)0.0017 (5)
H18A0.039970.035350.041820.004830.017690.00351
H18B0.055750.033690.022630.012540.000650.00135
H18C0.054430.022970.047390.004470.004740.01130
Geometric parameters (Å, º) top
O1—C31.3762 (14)C8—H81.0990
O1—H1A0.9671C9—C101.5266 (14)
O2—C71.4414 (15)C9—C111.5379 (17)
O2—H2A0.9873C9—H91.0990
O1W—H1W0.9597C11—C121.5411 (15)
O1W—H2W0.9609C11—H11B1.0920
O3—C171.2200 (18)C11—H11A1.0920
C1—C101.4067 (17)C12—C131.5259 (17)
C1—C21.3907 (16)C12—H12A1.0920
C1—H11.0830C12—H12B1.0920
C2—C31.3960 (18)C13—C171.5157 (15)
C2—H21.0830C13—C141.5443 (17)
C3—C41.3910 (17)C13—C181.5440 (18)
C4—C51.4007 (16)C14—C151.5374 (16)
C4—H41.0830C14—H141.0990
C5—C101.4032 (18)C15—C161.5479 (17)
C5—C61.5152 (16)C15—H15A1.0920
C6—C71.5251 (16)C15—H15B1.0920
C6—H6A1.0920C16—C171.5207 (18)
C6—H6B1.0920C16—H16A1.0920
C7—C81.5229 (17)C16—H16B1.0920
C7—H71.0990C18—H18A1.0770
C8—C141.5283 (14)C18—H18B1.0770
C8—C91.5480 (16)C18—H18C1.0770
C3—O1—H1A110.298C9—C11—C12112.85 (9)
C7—O2—H2A107.872C9—C11—H11B109.377
H1W—O1W—H2W104.856C9—C11—H11A109.363
C10—C1—C2122.00 (10)C12—C11—H11B109.058
C10—C1—H1119.091C12—C11—H11A108.890
C2—C1—H1118.906H11B—C11—H11A107.138
C3—C2—C1119.32 (10)C13—C12—C11110.21 (9)
C3—C2—H2120.357C13—C12—H12A109.660
C1—C2—H2120.322C13—C12—H12B109.472
O1—C3—C4117.93 (9)C11—C12—H12A109.839
O1—C3—C2122.23 (9)C11—C12—H12B109.577
C4—C3—C2119.79 (10)H12A—C12—H12B108.052
C3—C4—C5120.67 (10)C17—C13—C14100.16 (9)
C3—C4—H4119.743C17—C13—C12116.78 (8)
C5—C4—H4119.590C17—C13—C18104.67 (9)
C10—C5—C6122.16 (10)C14—C13—C12109.83 (9)
C10—C5—C4120.38 (10)C14—C13—C18113.19 (10)
C6—C5—C4117.41 (9)C12—C13—C18111.75 (10)
C7—C6—C5114.55 (9)C13—C14—C8111.38 (9)
C7—C6—H6A108.858C13—C14—C15104.43 (9)
C7—C6—H6B108.875C13—C14—H14105.785
C5—C6—H6A108.426C8—C14—C15121.63 (8)
C5—C6—H6B108.230C8—C14—H14106.174
H6A—C6—H6B107.698C15—C14—H14106.377
O2—C7—C8109.29 (9)C14—C15—C16102.19 (9)
O2—C7—C6111.45 (9)C14—C15—H15A111.263
O2—C7—H7109.308C14—C15—H15B111.075
C8—C7—C6109.52 (9)C16—C15—H15A111.309
C8—C7—H7108.486C16—C15—H15B111.045
C6—C7—H7108.737H15A—C15—H15B109.785
C7—C8—C14113.95 (9)C17—C16—C15105.62 (10)
C7—C8—C9111.68 (9)C17—C16—H16A110.326
C7—C8—H8108.212C17—C16—H16B110.355
C14—C8—C9107.60 (8)C15—C16—H16A110.752
C14—C8—H8107.547C15—C16—H16B110.948
C9—C8—H8107.599H16A—C16—H16B108.823
C8—C9—C10111.86 (9)O3—C17—C13126.06 (10)
C8—C9—C11110.54 (9)O3—C17—C16124.92 (10)
C8—C9—H9107.113C13—C17—C16109.02 (9)
C10—C9—C11113.19 (8)C13—C18—H18A110.242
C10—C9—H9107.065C13—C18—H18B109.893
C11—C9—H9106.688C13—C18—H18C109.759
C9—C10—C5120.92 (9)H18A—C18—H18B109.445
C9—C10—C1121.21 (9)H18A—C18—H18C109.152
C5—C10—C1117.82 (10)H18B—C18—H18C108.316
O1—C3—C4—C5176.00 (16)C8—C14—C15—H15B48.32
O1—C3—C4—H43.49C8—C9—C11—C1255.64 (17)
O1—C3—C2—C1175.81 (17)C8—C9—C11—H11B177.23
O1—C3—C2—H23.52C8—C9—C11—H11A65.72
H1A—O1—C3—C4176.65H8—C8—C14—C1354.18
H1A—O1—C3—C25.73H8—C8—C14—C1569.56
O2—C7—C8—C1461.83 (18)H8—C8—C14—H14168.87
O2—C7—C8—C960.35 (18)H8—C8—C9—C1069.34
O2—C7—C8—H8178.60H8—C8—C9—C1157.77
O2—C7—C6—C576.29 (17)H8—C8—C9—H9173.64
O2—C7—C6—H6A45.25C9—C8—C14—C1361.48 (18)
O2—C7—C6—H6B162.40C9—C8—C14—C15174.78 (17)
H2A—O2—C7—C8175.02C9—C8—C14—H1453.21
H2A—O2—C7—C663.79C9—C11—C12—C1353.86 (19)
H2A—O2—C7—H756.43C9—C11—C12—H12A67.06
O3—C17—C13—C14150.5 (3)C9—C11—C12—H12B174.39
O3—C17—C13—C1232.0 (2)H9—C9—C8—C1458.01
O3—C17—C13—C1892.1 (2)H9—C9—C11—C1260.49
O3—C17—C16—C15174.29 (15)H9—C9—C11—H11B61.10
O3—C17—C16—H16A65.98H9—C9—C11—H11A178.15
O3—C17—C16—H16B54.31C10—C9—C8—C14175.03 (17)
C1—C10—C9—C8162.4 (5)C10—C9—C11—C12177.98 (16)
C1—C10—C9—C1136.8 (2)C10—C9—C11—H11B56.39
C1—C10—C9—H980.52C10—C9—C11—H11A60.65
C1—C10—C5—C6178.13 (14)C11—C9—C8—C1457.85 (18)
C1—C10—C5—C40.63 (16)C11—C12—C13—C17168.2 (6)
C1—C2—C3—C41.77 (16)C11—C12—C13—C1455.12 (19)
H1—C1—C10—C93.10C11—C12—C13—C1871.36 (18)
H1—C1—C10—C5179.61H11A—C11—C12—C1367.77
H1—C1—C2—C3178.41H11A—C11—C12—H12A171.31
H1—C1—C2—H20.92H11A—C11—C12—H12B52.75
C2—C3—C4—C51.68 (16)H11B—C11—C12—C13175.63
C2—C3—C4—H4178.83H11B—C11—C12—H12A54.71
C2—C1—C10—C9177.82 (6)H11B—C11—C12—H12B63.84
C2—C1—C10—C50.52 (16)C12—C13—C17—C16147.3 (3)
H2—C2—C3—C4178.90C12—C13—C14—C15165.8 (7)
H2—C2—C1—C10180.00C12—C13—C14—H1453.76
C3—C4—C5—C100.47 (16)C12—C13—C18—H18A177.40
C3—C4—C5—C6177.15 (12)C12—C13—C18—H18B56.69
C3—C2—C1—C100.67 (16)C12—C13—C18—H18C62.33
C4—C5—C10—C9177.93 (6)H12A—C12—C13—C1747.16
C4—C5—C6—C7165.4 (7)H12A—C12—C13—C1465.91
C4—C5—C6—H6A43.59H12A—C12—C13—C18167.61
C4—C5—C6—H6B72.97H12B—C12—C13—C1771.22
H4—C4—C5—C10179.96H12B—C12—C13—C14175.71
H4—C4—C5—C62.34H12B—C12—C13—C1849.23
C5—C10—C9—C820.4 (2)C13—C17—C16—C155.06 (18)
C5—C10—C9—C11146.0 (4)C13—C17—C16—H16A114.67
C5—C10—C9—H996.69C13—C17—C16—H16B125.04
C5—C6—C7—C844.8 (2)C13—C14—C15—C1639.9 (2)
C5—C6—C7—H7163.15C13—C14—C15—H15A158.78
C6—C7—C8—C14175.82 (19)C13—C14—C15—H15B78.59
C6—C7—C8—C961.99 (16)C14—C13—C17—C1628.9 (3)
C6—C7—C8—H856.25C14—C13—C18—H18A52.78
C6—C5—C10—C94.57 (14)C14—C13—C18—H18B67.93
H6A—C6—C7—C8166.31C14—C13—C18—H18C173.05
H6A—C6—C7—H775.30C14—C15—C16—C1721.2 (3)
H6A—C6—C5—C10138.84C14—C15—C16—H16A140.67
H6B—C6—C7—C876.55C14—C15—C16—H16B98.37
H6B—C6—C7—H741.85H14—C14—C13—C1769.68
H6B—C6—C5—C10104.61H14—C14—C13—C18179.42
C7—C8—C14—C13174.12 (17)H14—C14—C15—C1671.72
C7—C8—C14—C1550.38 (19)H14—C14—C15—H15A47.16
C7—C8—C14—H1471.19H14—C14—C15—H15B169.79
C7—C8—C9—C1049.27 (19)C15—C14—C13—C1742.4 (2)
C7—C8—C9—C11176.38 (17)C15—C14—C13—C1868.54 (19)
C7—C8—C9—H967.75H15A—C15—C16—C17140.07
C7—C6—C5—C1017.1 (2)H15A—C15—C16—H16A100.48
H7—C7—C8—C1457.27H15A—C15—C16—H16B20.48
H7—C7—C8—C9179.46H15B—C15—C16—C1797.29
H7—C7—C8—H862.30H15B—C15—C16—H16A22.16
C8—C14—C13—C17175.39 (17)H15B—C15—C16—H16B143.12
C8—C14—C13—C1261.17 (17)C16—C17—C13—C1888.54 (19)
C8—C14—C13—C1864.49 (18)C17—C13—C18—H18A55.31
C8—C14—C15—C16166.8 (4)C17—C13—C18—H18B176.02
C8—C14—C15—H15A74.31C17—C13—C18—H18C64.96
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O1W0.971.732.6761 (17)167
C2—H2···O1W1.082.623.3530 (16)125
C8—H8···C181.102.663.1051 (19)103
C18—H18A···C151.082.643.019 (2)100
O1W—H1W···O3i0.961.852.8054 (14)171
O1W—H1W···C17i0.962.593.4934 (17)156
O2—H2A···O1ii0.991.892.8576 (17)166
O2—H2A···C3ii0.992.653.529 (2)149
C6—H6A···C2ii1.092.603.595 (2)151
C6—H6A···C3ii1.092.463.487 (2)156
O1W—H2W···O2iii0.961.802.7589 (17)173
C2—H2···O2iii1.082.513.580 (2)170
C16—H16B···O3iv1.092.453.354 (2)139
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1/2, z+1; (iii) x+2, y1/2, z+1; (iv) x+2, y+1/2, z.
 

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