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
CCDC references: 1832913; 1832912; 1832911
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.
3,7
α-Dihydroxyestra-1,3,5(10)-trien-17-one monohydrate (IAM_SHELXL)
top
Crystal data top
C18H22O3·H2O | F(000) = 328 |
Mr = 304.37 | Dx = 1.314 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
a = 6.143 (3) Å | Cell parameters from 2931 reflections |
b = 8.4833 (17) Å | θ = 3.0–72.2° |
c = 14.767 (3) Å | µ = 0.74 mm−1 |
β = 91.94 (2)° | T = 100 K |
V = 769.2 (4) Å3 | Block, colorless |
Z = 2 | 0.46 × 0.22 × 0.12 mm |
Data collection top
Bruker D8 Venture PHOTON II Detector diffractometer | 2905 reflections with I > 2σ(I) |
Radiation source: Microfocus | Rint = 0.043 |
ω and phi scan | θmax = 72.2°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −7→7 |
Tmin = 0.727, Tmax = 0.916 | k = −10→10 |
9196 measured reflections | l = −18→18 |
2931 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.10 | Δρmax = 0.34 e Å−3 |
2931 reflections | Δρmin = −0.27 e Å−3 |
216 parameters | Absolute structure: Flack x determined using 1292 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
1 restraint | Absolute 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.6688 (3) | 0.5239 (2) | 0.69523 (11) | 0.0141 (4) | |
H1A | 0.774 (6) | 0.490 (5) | 0.730 (2) | 0.030 (9)* | |
O2 | 0.6550 (3) | 0.7883 (2) | 0.27748 (12) | 0.0148 (4) | |
H2A | 0.574 (6) | 0.870 (6) | 0.289 (3) | 0.033 (10)* | |
O1W | 0.9626 (3) | 0.3746 (3) | 0.80166 (12) | 0.0201 (4) | |
H1W | 0.981 (6) | 0.370 (5) | 0.856 (3) | 0.027 (9)* | |
H2W | 1.078 (7) | 0.343 (5) | 0.783 (3) | 0.028 (9)* | |
O3 | 1.0195 (3) | 0.3311 (3) | −0.01042 (12) | 0.0231 (5) | |
C1 | 0.9590 (4) | 0.4364 (3) | 0.48721 (16) | 0.0124 (5) | |
H1 | 1.0902 | 0.3880 | 0.4693 | 0.015* | |
C2 | 0.9183 (4) | 0.4486 (3) | 0.57874 (16) | 0.0136 (5) | |
H2 | 1.0214 | 0.4102 | 0.6228 | 0.016* | |
C3 | 0.7254 (4) | 0.5174 (3) | 0.60558 (16) | 0.0125 (5) | |
C4 | 0.5790 (4) | 0.5774 (3) | 0.54083 (16) | 0.0131 (5) | |
H4 | 0.4494 | 0.6271 | 0.5594 | 0.016* | |
C5 | 0.6200 (4) | 0.5654 (3) | 0.44851 (16) | 0.0118 (5) | |
C6 | 0.4464 (4) | 0.6267 (3) | 0.38191 (16) | 0.0128 (5) | |
H6A | 0.3933 | 0.7294 | 0.4041 | 0.015* | |
H6B | 0.3219 | 0.5526 | 0.3806 | 0.015* | |
C7 | 0.5227 (4) | 0.6481 (3) | 0.28548 (16) | 0.0116 (5) | |
H7 | 0.3922 | 0.6576 | 0.2435 | 0.014* | |
C8 | 0.6552 (4) | 0.5052 (3) | 0.25817 (15) | 0.0110 (5) | |
H8 | 0.5623 | 0.4096 | 0.2656 | 0.013* | |
C9 | 0.8621 (4) | 0.4845 (3) | 0.31968 (15) | 0.0104 (5) | |
H9 | 0.9604 | 0.5752 | 0.3067 | 0.013* | |
C10 | 0.8115 (4) | 0.4937 (3) | 0.42027 (15) | 0.0108 (5) | |
C11 | 0.9846 (4) | 0.3337 (3) | 0.29445 (15) | 0.0129 (5) | |
H11A | 0.8934 | 0.2411 | 0.3082 | 0.015* | |
H11B | 1.1203 | 0.3263 | 0.3323 | 0.015* | |
C12 | 1.0424 (4) | 0.3285 (3) | 0.19371 (15) | 0.0131 (5) | |
H12A | 1.1505 | 0.4116 | 0.1813 | 0.016* | |
H12B | 1.1081 | 0.2251 | 0.1797 | 0.016* | |
C13 | 0.8380 (4) | 0.3538 (3) | 0.13362 (15) | 0.0128 (5) | |
C14 | 0.7266 (4) | 0.5091 (3) | 0.15995 (15) | 0.0113 (5) | |
H14 | 0.8409 | 0.5927 | 0.1572 | 0.014* | |
C15 | 0.5634 (4) | 0.5425 (3) | 0.08079 (15) | 0.0150 (5) | |
H15A | 0.5223 | 0.6553 | 0.0783 | 0.018* | |
H15B | 0.4302 | 0.4776 | 0.0854 | 0.018* | |
C16 | 0.6951 (4) | 0.4945 (3) | −0.00233 (15) | 0.0145 (5) | |
H16A | 0.6002 | 0.4404 | −0.0481 | 0.017* | |
H16B | 0.7598 | 0.5886 | −0.0306 | 0.017* | |
C17 | 0.8726 (4) | 0.3840 (3) | 0.03380 (16) | 0.0144 (5) | |
C18 | 0.6847 (4) | 0.2096 (3) | 0.13510 (17) | 0.0169 (5) | |
H18A | 0.5525 | 0.2319 | 0.0983 | 0.025* | |
H18B | 0.6455 | 0.1876 | 0.1976 | 0.025* | |
H18C | 0.7588 | 0.1177 | 0.1103 | 0.025* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0172 (8) | 0.0134 (9) | 0.0116 (8) | −0.0012 (7) | −0.0026 (6) | −0.0006 (6) |
O2 | 0.0149 (8) | 0.0080 (9) | 0.0215 (8) | 0.0008 (7) | 0.0007 (6) | 0.0014 (7) |
O1W | 0.0199 (9) | 0.0266 (11) | 0.0137 (9) | 0.0079 (8) | −0.0012 (7) | 0.0011 (8) |
O3 | 0.0279 (10) | 0.0280 (11) | 0.0134 (8) | 0.0139 (8) | 0.0013 (7) | 0.0012 (8) |
C1 | 0.0111 (10) | 0.0088 (11) | 0.0170 (11) | 0.0002 (9) | −0.0033 (8) | −0.0004 (9) |
C2 | 0.0145 (10) | 0.0109 (11) | 0.0151 (11) | −0.0012 (9) | −0.0049 (8) | 0.0015 (9) |
C3 | 0.0176 (11) | 0.0062 (11) | 0.0134 (10) | −0.0044 (9) | −0.0024 (8) | −0.0008 (9) |
C4 | 0.0144 (11) | 0.0085 (11) | 0.0164 (11) | −0.0001 (9) | −0.0016 (8) | −0.0018 (9) |
C5 | 0.0124 (10) | 0.0066 (11) | 0.0162 (11) | −0.0015 (9) | −0.0037 (8) | −0.0001 (9) |
C6 | 0.0111 (10) | 0.0126 (12) | 0.0144 (11) | 0.0022 (9) | −0.0017 (8) | 0.0015 (9) |
C7 | 0.0107 (10) | 0.0093 (11) | 0.0146 (11) | −0.0001 (9) | −0.0027 (8) | 0.0017 (9) |
C8 | 0.0111 (10) | 0.0100 (11) | 0.0116 (10) | 0.0000 (9) | −0.0045 (8) | 0.0006 (9) |
C9 | 0.0108 (10) | 0.0092 (11) | 0.0112 (10) | 0.0016 (9) | −0.0034 (8) | 0.0011 (8) |
C10 | 0.0129 (10) | 0.0077 (10) | 0.0116 (10) | −0.0010 (9) | −0.0021 (8) | −0.0006 (9) |
C11 | 0.0157 (11) | 0.0111 (11) | 0.0117 (10) | 0.0027 (9) | −0.0033 (8) | 0.0003 (9) |
C12 | 0.0163 (11) | 0.0105 (12) | 0.0124 (10) | 0.0043 (9) | −0.0014 (8) | −0.0003 (9) |
C13 | 0.0157 (11) | 0.0110 (12) | 0.0114 (10) | 0.0009 (9) | −0.0038 (8) | −0.0008 (9) |
C14 | 0.0121 (10) | 0.0088 (11) | 0.0125 (11) | 0.0011 (9) | −0.0048 (8) | 0.0003 (9) |
C15 | 0.0163 (11) | 0.0160 (12) | 0.0125 (10) | 0.0052 (9) | −0.0041 (9) | 0.0024 (9) |
C16 | 0.0166 (11) | 0.0142 (11) | 0.0123 (10) | 0.0028 (10) | −0.0044 (8) | 0.0010 (9) |
C17 | 0.0194 (11) | 0.0099 (11) | 0.0134 (11) | 0.0017 (10) | −0.0049 (8) | −0.0002 (9) |
C18 | 0.0239 (13) | 0.0100 (11) | 0.0166 (11) | −0.0019 (10) | −0.0049 (9) | −0.0014 (9) |
Geometric parameters (Å, º) top
O1—C3 | 1.381 (3) | C8—H8 | 1.0000 |
O1—H1A | 0.87 (4) | C9—C10 | 1.530 (3) |
O2—C7 | 1.447 (3) | C9—C11 | 1.536 (3) |
O2—H2A | 0.87 (5) | C9—H9 | 1.0000 |
O1W—O1W | 0.000 (6) | C11—C12 | 1.542 (3) |
O1W—H1W | 0.81 (4) | C11—H11A | 0.9900 |
O1W—H2W | 0.81 (4) | C11—H11B | 0.9900 |
O3—C17 | 1.217 (3) | C12—C13 | 1.528 (3) |
C1—C2 | 1.387 (3) | C12—H12A | 0.9900 |
C1—C10 | 1.405 (3) | C12—H12B | 0.9900 |
C1—H1 | 0.9500 | C13—C17 | 1.518 (3) |
C2—C3 | 1.391 (4) | C13—C14 | 1.540 (3) |
C2—H2 | 0.9500 | C13—C18 | 1.544 (3) |
C3—C4 | 1.387 (3) | C14—C15 | 1.541 (3) |
C4—C5 | 1.398 (3) | C14—H14 | 1.0000 |
C4—H4 | 0.9500 | C15—C16 | 1.547 (3) |
C5—C10 | 1.401 (3) | C15—H15A | 0.9900 |
C5—C6 | 1.518 (3) | C15—H15B | 0.9900 |
C6—C7 | 1.525 (3) | C16—C17 | 1.521 (3) |
C6—H6A | 0.9900 | C16—H16A | 0.9900 |
C6—H6B | 0.9900 | C16—H16B | 0.9900 |
C7—C8 | 1.523 (3) | C18—H18A | 0.9800 |
C7—H7 | 1.0000 | C18—H18B | 0.9800 |
C8—C14 | 1.530 (3) | C18—H18C | 0.9800 |
C8—C9 | 1.547 (3) | | |
| | | |
C3—O1—H1A | 111 (2) | C1—C10—C9 | 121.2 (2) |
C7—O2—H2A | 108 (3) | C9—C11—C12 | 112.87 (18) |
O1W—O1W—H1W | 0 (10) | C9—C11—H11A | 109.0 |
O1W—O1W—H2W | 0 (10) | C12—C11—H11A | 109.0 |
H1W—O1W—H2W | 103 (4) | C9—C11—H11B | 109.0 |
C2—C1—C10 | 121.8 (2) | C12—C11—H11B | 109.0 |
C2—C1—H1 | 119.1 | H11A—C11—H11B | 107.8 |
C10—C1—H1 | 119.1 | C13—C12—C11 | 110.15 (18) |
C1—C2—C3 | 119.5 (2) | C13—C12—H12A | 109.6 |
C1—C2—H2 | 120.2 | C11—C12—H12A | 109.6 |
C3—C2—H2 | 120.2 | C13—C12—H12B | 109.6 |
O1—C3—C4 | 117.9 (2) | C11—C12—H12B | 109.6 |
O1—C3—C2 | 122.3 (2) | H12A—C12—H12B | 108.1 |
C4—C3—C2 | 119.8 (2) | C17—C13—C12 | 116.61 (19) |
C3—C4—C5 | 120.7 (2) | C17—C13—C14 | 100.30 (19) |
C3—C4—H4 | 119.6 | C12—C13—C14 | 109.68 (19) |
C5—C4—H4 | 119.6 | C17—C13—C18 | 104.66 (18) |
C4—C5—C10 | 120.17 (19) | C12—C13—C18 | 111.7 (2) |
C4—C5—C6 | 117.5 (2) | C14—C13—C18 | 113.43 (19) |
C10—C5—C6 | 122.3 (2) | C8—C14—C13 | 111.41 (18) |
C5—C6—C7 | 114.50 (19) | C8—C14—C15 | 121.54 (18) |
C5—C6—H6A | 108.6 | C13—C14—C15 | 104.42 (19) |
C7—C6—H6A | 108.6 | C8—C14—H14 | 106.2 |
C5—C6—H6B | 108.6 | C13—C14—H14 | 106.2 |
C7—C6—H6B | 108.6 | C15—C14—H14 | 106.2 |
H6A—C6—H6B | 107.6 | C14—C15—C16 | 102.07 (18) |
O2—C7—C8 | 109.01 (18) | C14—C15—H15A | 111.4 |
O2—C7—C6 | 111.41 (19) | C16—C15—H15A | 111.4 |
C8—C7—C6 | 109.67 (19) | C14—C15—H15B | 111.4 |
O2—C7—H7 | 108.9 | C16—C15—H15B | 111.4 |
C8—C7—H7 | 108.9 | H15A—C15—H15B | 109.2 |
C6—C7—H7 | 108.9 | C17—C16—C15 | 105.76 (19) |
C7—C8—C14 | 114.03 (18) | C17—C16—H16A | 110.6 |
C7—C8—C9 | 111.77 (18) | C15—C16—H16A | 110.6 |
C14—C8—C9 | 107.62 (17) | C17—C16—H16B | 110.6 |
C7—C8—H8 | 107.7 | C15—C16—H16B | 110.6 |
C14—C8—H8 | 107.7 | H16A—C16—H16B | 108.7 |
C9—C8—H8 | 107.7 | O3—C17—C13 | 126.1 (2) |
C10—C9—C11 | 113.27 (17) | O3—C17—C16 | 125.1 (2) |
C10—C9—C8 | 111.99 (18) | C13—C17—C16 | 108.8 (2) |
C11—C9—C8 | 110.57 (18) | C13—C18—H18A | 109.5 |
C10—C9—H9 | 106.9 | C13—C18—H18B | 109.5 |
C11—C9—H9 | 106.9 | H18A—C18—H18B | 109.5 |
C8—C9—H9 | 106.9 | C13—C18—H18C | 109.5 |
C5—C10—C1 | 118.0 (2) | H18A—C18—H18C | 109.5 |
C5—C10—C9 | 120.76 (19) | H18B—C18—H18C | 109.5 |
| | | |
C10—C1—C2—C3 | 0.8 (4) | C8—C9—C10—C1 | 162.4 (2) |
C1—C2—C3—O1 | 175.8 (2) | C10—C9—C11—C12 | −177.84 (17) |
C1—C2—C3—C4 | −1.9 (4) | C8—C9—C11—C12 | 55.5 (2) |
O1—C3—C4—C5 | −175.9 (2) | C9—C11—C12—C13 | −53.9 (3) |
C2—C3—C4—C5 | 1.9 (4) | C11—C12—C13—C17 | 168.4 (2) |
C3—C4—C5—C10 | −0.7 (3) | C11—C12—C13—C14 | 55.3 (3) |
C3—C4—C5—C6 | 177.1 (2) | C11—C12—C13—C18 | −71.4 (3) |
C4—C5—C6—C7 | 165.5 (2) | C7—C8—C14—C13 | −173.83 (18) |
C10—C5—C6—C7 | −16.8 (3) | C9—C8—C14—C13 | 61.6 (2) |
C5—C6—C7—O2 | −76.3 (3) | C7—C8—C14—C15 | −50.2 (3) |
C5—C6—C7—C8 | 44.5 (3) | C9—C8—C14—C15 | −174.7 (2) |
O2—C7—C8—C14 | −61.8 (2) | C17—C13—C14—C8 | 175.36 (17) |
C6—C7—C8—C14 | 175.94 (18) | C12—C13—C14—C8 | −61.4 (2) |
O2—C7—C8—C9 | 60.5 (2) | C18—C13—C14—C8 | 64.3 (2) |
C6—C7—C8—C9 | −61.7 (2) | C17—C13—C14—C15 | 42.4 (2) |
C7—C8—C9—C10 | 49.0 (3) | C12—C13—C14—C15 | 165.7 (2) |
C14—C8—C9—C10 | 174.96 (19) | C18—C13—C14—C15 | −68.6 (2) |
C7—C8—C9—C11 | 176.37 (18) | C8—C14—C15—C16 | −166.9 (2) |
C14—C8—C9—C11 | −57.7 (2) | C13—C14—C15—C16 | −40.0 (2) |
C4—C5—C10—C1 | −0.5 (3) | C14—C15—C16—C17 | 21.3 (3) |
C6—C5—C10—C1 | −178.1 (2) | C12—C13—C17—O3 | 31.8 (4) |
C4—C5—C10—C9 | −178.0 (2) | C14—C13—C17—O3 | 150.0 (3) |
C6—C5—C10—C9 | 4.4 (3) | C18—C13—C17—O3 | −92.2 (3) |
C2—C1—C10—C5 | 0.4 (3) | C12—C13—C17—C16 | −147.2 (2) |
C2—C1—C10—C9 | 177.9 (2) | C14—C13—C17—C16 | −28.9 (2) |
C11—C9—C10—C5 | −146.1 (2) | C18—C13—C17—C16 | 88.8 (2) |
C8—C9—C10—C5 | −20.2 (3) | C15—C16—C17—O3 | −174.0 (2) |
C11—C9—C10—C1 | 36.5 (3) | C15—C16—C17—C13 | 4.9 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O1W | 0.87 (4) | 1.82 (4) | 2.672 (3) | 167 (4) |
O2—H2A···O1i | 0.87 (5) | 2.00 (5) | 2.858 (3) | 166 (4) |
O1W—H1W···O3ii | 0.81 (4) | 2.00 (4) | 2.809 (3) | 173 (4) |
O1W—H2W···O2iii | 0.81 (4) | 1.95 (4) | 2.758 (3) | 171 (4) |
C16—H16B···O3iv | 0.99 | 2.53 | 3.353 (3) | 141 |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x, y, z+1; (iii) −x+2, y−1/2, −z+1; (iv) −x+2, y+1/2, −z. |
3,7
α-Dihydroxyestra-1,3,5(10)-trien-17-one monohydrate (IAM_MoPro)
top
Crystal data top
C18H22O3·H2O | F(000) = 328 |
Mr = 304.37 | Dx = 1.315 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2yb | Cell parameters from 2931 reflections |
a = 6.143 (3) Å | θ = 3.0–72.2° |
b = 8.4833 (17) Å | µ = 0.74 mm−1 |
c = 14.767 (3) Å | T = 100 K |
β = 91.94 (2)° | Block, colorless |
V = 769.2 (4) Å3 | 0.46 × 0.22 × 0.12 mm |
Z = 2 | |
Data collection top
Bruker D8 Venture PHOTON II Detector diffractometer | 2931 independent reflections |
Radiation source: Microfocus | 2905 reflections with > 2.0σ(I) |
Graphite monochromator | Rint = 0.043 |
ω and phi scan | θmax = 72.2°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = 0→7 |
Tmin = 0.727, Tmax = 0.916 | k = −10→10 |
9196 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.134 | Only 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 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.6691 (2) | 0.5303 (18) | 0.69523 (9) | 0.0145 (2) | |
H1A | 0.771 (7) | 0.497 (6) | 0.729 (3) | 0.02703 | |
O2 | 0.6550 (2) | 0.7949 (18) | 0.27754 (9) | 0.0150 (2) | |
H2A | 0.569 (7) | 0.878 (6) | 0.287 (3) | 0.02693 | |
O1W | 0.9627 (2) | 0.3808 (18) | 0.80172 (10) | 0.0210 (3) | |
H1W | 0.981 (7) | 0.383 (7) | 0.857 (3) | 0.03779 | |
H2W | 1.089 (7) | 0.352 (6) | 0.778 (3) | 0.03638 | |
O3 | 1.0190 (3) | 0.3374 (18) | −0.01060 (10) | 0.0237 (3) | |
C1 | 0.9593 (3) | 0.4431 (18) | 0.48726 (13) | 0.0131 (3) | |
H1 | 1.108 (17) | 0.387 (5) | 0.467 (2) | 0.02779 | |
C2 | 0.9186 (3) | 0.4551 (18) | 0.57883 (13) | 0.0142 (3) | |
H2 | 1.036 (5) | 0.411 (5) | 0.629 (17) | 0.02932 | |
C3 | 0.7256 (3) | 0.5237 (18) | 0.60563 (13) | 0.0126 (3) | |
C4 | 0.5789 (3) | 0.5840 (18) | 0.54091 (13) | 0.0133 (3) | |
H4 | 0.431 (17) | 0.640 (5) | 0.562 (3) | 0.02804 | |
C5 | 0.6200 (3) | 0.5721 (18) | 0.44843 (13) | 0.0122 (3) | |
C6 | 0.4462 (3) | 0.6331 (18) | 0.38198 (13) | 0.0136 (3) | |
H6A | 0.387 (6) | 0.746 (17) | 0.407 (2) | 0.02937 | |
H6B | 0.309 (5) | 0.551 (17) | 0.381 (3) | 0.02862 | |
C7 | 0.5231 (3) | 0.6547 (19) | 0.28560 (13) | 0.0120 (3) | |
H7 | 0.380 (4) | 0.665 (6) | 0.239 (17) | 0.02545 | |
C8 | 0.6548 (3) | 0.5115 (18) | 0.25829 (12) | 0.0111 (3) | |
H8 | 0.553 (5) | 0.406 (17) | 0.266 (3) | 0.02337 | |
C9 | 0.8624 (3) | 0.4910 (18) | 0.31962 (12) | 0.0108 (3) | |
H9 | 0.971 (5) | 0.590 (17) | 0.305 (3) | 0.02281 | |
C10 | 0.8115 (3) | 0.5000 (19) | 0.42027 (12) | 0.0111 (3) | |
C11 | 0.9845 (3) | 0.3399 (18) | 0.29438 (12) | 0.0135 (3) | |
H11A | 0.884 (6) | 0.238 (17) | 0.310 (3) | 0.02872 | |
H11B | 1.134 (3) | 0.331 (6) | 0.336 (17) | 0.02925 | |
C12 | 1.0428 (3) | 0.3350 (18) | 0.19373 (12) | 0.0136 (3) | |
H12A | 1.162 (5) | 0.426 (17) | 0.180 (3) | 0.03017 | |
H12B | 1.115 (7) | 0.221 (17) | 0.178 (3) | 0.03286 | |
C13 | 0.8378 (3) | 0.3600 (18) | 0.13353 (12) | 0.0136 (3) | |
C14 | 0.7264 (3) | 0.5152 (19) | 0.15996 (12) | 0.0115 (3) | |
H14 | 0.852 (5) | 0.607 (17) | 0.157 (3) | 0.02364 | |
C15 | 0.5631 (3) | 0.5489 (18) | 0.08092 (12) | 0.0155 (3) | |
H15A | 0.518 (7) | 0.673 (17) | 0.078 (3) | 0.03038 | |
H15B | 0.417 (17) | 0.477 (5) | 0.086 (3) | 0.03153 | |
C16 | 0.6949 (3) | 0.5010 (18) | −0.00233 (12) | 0.0153 (3) | |
H16A | 0.591 (6) | 0.441 (5) | −0.053 (17) | 0.03449 | |
H16B | 0.767 (6) | 0.604 (17) | −0.034 (3) | 0.03202 | |
C17 | 0.8725 (3) | 0.3904 (18) | 0.03395 (13) | 0.0146 (3) | |
C18 | 0.6848 (3) | 0.2162 (18) | 0.13490 (13) | 0.0177 (3) | |
H18A | 0.539 (4) | 0.240 (6) | 0.094 (17) | 0.03948 | |
H18B | 0.642 (8) | 0.191 (6) | 0.204 (17) | 0.03737 | |
H18C | 0.766 (7) | 0.115 (17) | 0.108 (3) | 0.04153 | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0176 (6) | 0.0141 (7) | 0.0117 (6) | −0.0003 (5) | −0.0019 (5) | −0.0012 (5) |
H1A | 0.02706 | 0.03136 | 0.02233 | 0.00451 | −0.00430 | 0.00016 |
O2 | 0.0144 (6) | 0.0091 (7) | 0.0216 (7) | 0.0011 (5) | 0.0009 (5) | 0.0012 (5) |
H2A | 0.03105 | 0.01544 | 0.03446 | 0.00548 | 0.00326 | 0.00141 |
O1W | 0.0208 (7) | 0.0274 (9) | 0.0147 (7) | 0.0072 (6) | −0.0016 (5) | 0.0022 (6) |
H1W | 0.04395 | 0.05082 | 0.01821 | 0.00667 | −0.00468 | 0.00094 |
H2W | 0.02978 | 0.04780 | 0.03155 | 0.01047 | 0.00111 | −0.00082 |
O3 | 0.0293 (8) | 0.0280 (9) | 0.0137 (6) | 0.0140 (7) | 0.0012 (5) | 0.0002 (6) |
C1 | 0.0124 (8) | 0.0096 (9) | 0.0170 (9) | −0.0006 (7) | −0.0042 (6) | −0.0007 (7) |
H1 | 0.02197 | 0.03414 | 0.02717 | 0.00888 | −0.00037 | −0.00007 |
C2 | 0.0153 (8) | 0.0113 (9) | 0.0156 (9) | −0.0012 (7) | −0.0043 (6) | 0.0014 (7) |
H2 | 0.02675 | 0.03748 | 0.02314 | 0.00692 | −0.00765 | 0.00240 |
C3 | 0.0174 (8) | 0.0058 (9) | 0.0144 (8) | −0.0052 (7) | −0.0029 (6) | 0.0000 (7) |
C4 | 0.0151 (8) | 0.0086 (8) | 0.0161 (9) | −0.0005 (7) | −0.0023 (6) | −0.0020 (7) |
H4 | 0.02474 | 0.03053 | 0.02896 | 0.00864 | 0.00237 | −0.00087 |
C5 | 0.0126 (8) | 0.0072 (9) | 0.0167 (8) | −0.0010 (7) | −0.0031 (6) | 0.0000 (7) |
C6 | 0.0125 (8) | 0.0142 (10) | 0.0139 (8) | 0.0020 (7) | −0.0016 (6) | 0.0024 (7) |
H6A | 0.03667 | 0.02074 | 0.03065 | 0.00916 | 0.00047 | −0.00151 |
H6B | 0.02316 | 0.03043 | 0.03196 | −0.00917 | −0.00359 | 0.00363 |
C7 | 0.0115 (8) | 0.0091 (9) | 0.0151 (8) | 0.0004 (7) | −0.0022 (6) | 0.0021 (7) |
H7 | 0.02021 | 0.02912 | 0.02652 | 0.00301 | −0.00676 | 0.00291 |
C8 | 0.0109 (8) | 0.0108 (8) | 0.0114 (8) | 0.0008 (7) | −0.0046 (6) | −0.0001 (7) |
H8 | 0.02430 | 0.01689 | 0.02868 | −0.00739 | −0.00288 | 0.00072 |
C9 | 0.0103 (7) | 0.0104 (9) | 0.0115 (8) | 0.0017 (7) | −0.0036 (6) | 0.0003 (7) |
H9 | 0.02167 | 0.01778 | 0.02886 | −0.00632 | −0.00097 | 0.00246 |
C10 | 0.0135 (8) | 0.0085 (8) | 0.0112 (8) | 0.0001 (7) | −0.0024 (6) | −0.0007 (7) |
C11 | 0.0167 (8) | 0.0126 (9) | 0.0110 (8) | 0.0032 (7) | −0.0030 (6) | 0.0000 (7) |
H11A | 0.03655 | 0.01767 | 0.03204 | −0.00378 | 0.00287 | −0.00013 |
H11B | 0.02460 | 0.03568 | 0.02691 | 0.00779 | −0.00750 | −0.00081 |
C12 | 0.0175 (9) | 0.0114 (9) | 0.0119 (8) | 0.0046 (7) | −0.0014 (6) | 0.0003 (7) |
H12A | 0.02907 | 0.03178 | 0.02948 | −0.00280 | −0.00150 | 0.00574 |
H12B | 0.04432 | 0.02512 | 0.02894 | 0.01663 | −0.00201 | −0.00150 |
C13 | 0.0163 (9) | 0.0115 (10) | 0.0127 (8) | 0.0010 (7) | −0.0041 (6) | −0.0007 (7) |
C14 | 0.0126 (8) | 0.0094 (9) | 0.0123 (8) | 0.0016 (7) | −0.0047 (6) | 0.0002 (7) |
H14 | 0.02192 | 0.01980 | 0.02905 | −0.00377 | −0.00134 | 0.00257 |
C15 | 0.0166 (8) | 0.0182 (10) | 0.0113 (8) | 0.0051 (7) | −0.0039 (6) | 0.0027 (7) |
H15A | 0.03665 | 0.02393 | 0.03029 | 0.00882 | −0.00279 | 0.00352 |
H15B | 0.02636 | 0.03797 | 0.02990 | −0.00855 | −0.00436 | 0.00059 |
C16 | 0.0173 (8) | 0.0152 (9) | 0.0131 (8) | 0.0030 (8) | −0.0038 (6) | 0.0002 (8) |
H16A | 0.03392 | 0.04041 | 0.02838 | 0.00303 | −0.00994 | −0.00706 |
H16B | 0.03317 | 0.02901 | 0.03405 | 0.00454 | 0.00353 | 0.00855 |
C17 | 0.0199 (9) | 0.0099 (9) | 0.0138 (9) | 0.0011 (8) | −0.0050 (6) | 0.0004 (7) |
C18 | 0.0238 (10) | 0.0115 (9) | 0.0173 (9) | −0.0027 (8) | −0.0054 (7) | −0.0009 (7) |
H18A | 0.03997 | 0.03535 | 0.04182 | −0.00483 | −0.01769 | 0.00351 |
H18B | 0.05575 | 0.03369 | 0.02263 | −0.01254 | 0.00065 | −0.00135 |
H18C | 0.05443 | 0.02297 | 0.04739 | 0.00447 | 0.00474 | −0.01130 |
Geometric parameters (Å, º) top
O1—C3 | 1.3804 (9) | C8—H8 | 1.10 (5) |
O1—H1A | 0.84 (3) | C9—C10 | 1.5311 (8) |
O2—C7 | 1.4463 (9) | C9—C11 | 1.5368 (10) |
O2—H2A | 0.89 (3) | C9—H9 | 1.10 (5) |
O1W—H1W | 0.83 (3) | C11—C12 | 1.5412 (8) |
O1W—H2W | 0.89 (3) | C11—H11B | 1.09 (6) |
O3—C17 | 1.2187 (12) | C11—H11A | 1.09 (5) |
C1—C10 | 1.4057 (11) | C12—C13 | 1.5317 (11) |
C1—C2 | 1.3872 (10) | C12—H12B | 1.09 (6) |
C1—H1 | 1.08 (4) | C12—H12A | 1.09 (5) |
C2—C3 | 1.3900 (12) | C13—C17 | 1.5151 (8) |
C2—H2 | 1.08 (8) | C13—C14 | 1.5404 (10) |
C3—C4 | 1.3887 (11) | C13—C18 | 1.5409 (10) |
C4—C5 | 1.4008 (9) | C14—C15 | 1.5398 (10) |
C4—H4 | 1.08 (4) | C14—H14 | 1.10 (5) |
C5—C10 | 1.4014 (11) | C15—C16 | 1.5492 (10) |
C5—C6 | 1.5165 (10) | C15—H15A | 1.09 (6) |
C6—C7 | 1.5256 (9) | C15—H15B | 1.09 (4) |
C6—H6A | 1.09 (6) | C16—C17 | 1.5224 (11) |
C6—H6B | 1.09 (4) | C16—H16A | 1.09 (8) |
C7—C8 | 1.5214 (10) | C16—H16B | 1.09 (5) |
C7—H7 | 1.10 (7) | C18—H18A | 1.08 (6) |
C8—C14 | 1.5317 (8) | C18—H18B | 1.08 (11) |
C8—C9 | 1.5491 (10) | C18—H18C | 1.08 (5) |
| | | |
C3—O1—H1A | 111 (12) | C11—C9—H9 | 107 (24) |
C7—O2—H2A | 108 (12) | C12—C11—H11B | 109 (49) |
H1W—O1W—H2W | 108 (17) | C12—C11—H11A | 109 (12) |
C10—C1—C2 | 121.8 (7) | H11B—C11—H11A | 107 (24) |
C10—C1—H1 | 119 (16) | C13—C12—C11 | 110.0 (6) |
C2—C1—H1 | 119 (12) | C13—C12—H12B | 109 (12) |
C3—C2—C1 | 119.5 (7) | C13—C12—H12A | 110 (13) |
C3—C2—H2 | 120 (34) | H12B—C12—H12A | 108 (33) |
C4—C3—C2 | 119.9 (7) | C17—C13—C14 | 100.3 (6) |
C5—C4—H4 | 119 (13) | C17—C13—C12 | 116.5 (6) |
C10—C5—C6 | 122.5 (7) | C17—C13—C18 | 104.7 (6) |
C10—C5—C4 | 120.1 (7) | C14—C13—C12 | 109.6 (6) |
C6—C5—C4 | 117.4 (6) | C14—C13—C18 | 113.4 (6) |
C7—C6—C5 | 114.3 (6) | C15—C14—H14 | 106 (13) |
C7—C6—H6A | 109 (14) | C16—C15—H15A | 111 (14) |
C7—C6—H6B | 109 (10) | C16—C15—H15B | 111 (14) |
H6A—C6—H6B | 108 (31) | H15A—C15—H15B | 110 (22) |
C8—C7—C6 | 109.6 (6) | C17—C16—C15 | 105.7 (6) |
C8—C7—H7 | 109 (24) | C17—C16—H16A | 110 (19) |
C14—C8—C9 | 107.4 (5) | C17—C16—H16B | 110 (18) |
C14—C8—H8 | 108 (11) | H16A—C16—H16B | 109 (35) |
C9—C8—H8 | 108 (12) | H18A—C18—H18B | 109 (56) |
C10—C9—C11 | 113.2 (6) | H18A—C18—H18C | 109 (32) |
C10—C9—H9 | 107 (11) | H18B—C18—H18C | 109 (27) |
| | | |
O1—C3—C4—C5 | −175.99 (13) | C8—C14—C15—H15B | −48 (3) |
O1—C3—C4—H4 | 4 (2) | C8—C9—C11—C12 | 55.95 (13) |
O1—C3—C2—C1 | 175.82 (13) | C8—C9—C11—H11B | 177.2 (10) |
O1—C3—C2—H2 | −4 (9) | C8—C9—C11—H11A | −66 (3) |
H1A—O1—C3—C4 | −176.2 (9) | H8—C8—C14—C13 | −54 (6) |
H1A—O1—C3—C2 | 6 (3) | H8—C8—C14—C15 | 70 (3) |
O2—C7—C8—C14 | −61.66 (14) | H8—C8—C14—H14 | −169 (6) |
O2—C7—C8—C9 | 60.34 (14) | H8—C8—C9—C10 | −69 (2) |
O2—C7—C8—H8 | 178.7 (4) | H8—C8—C9—C11 | 58 (6) |
O2—C7—C6—C5 | −76.28 (14) | H8—C8—C9—H9 | 174 (5) |
O2—C7—C6—H6A | 45 (6) | C9—C8—C14—C13 | 61.61 (14) |
O2—C7—C6—H6B | 162 (5) | C9—C8—C14—C15 | −174.55 (13) |
H2A—O2—C7—C8 | 172.5 (8) | C9—C8—C14—H14 | −53 (4) |
H2A—O2—C7—C6 | −66 (3) | C9—C11—C12—C13 | −54.22 (15) |
H2A—O2—C7—H7 | 54 (6) | C9—C11—C12—H12B | −175 (1) |
O3—C17—C13—C14 | 150.3 (3) | C9—C11—C12—H12A | 67 (6) |
O3—C17—C13—C12 | 32.18 (16) | H9—C9—C8—C14 | 58 (3) |
O3—C17—C13—C18 | −91.98 (17) | H9—C9—C11—C12 | −60 (3) |
O3—C17—C16—C15 | −174.23 (12) | H9—C9—C11—H11B | 61 (6) |
O3—C17—C16—H16A | 66 (7) | H9—C9—C11—H11A | 178 (6) |
O3—C17—C16—H16B | −54 (4) | C10—C9—C8—C14 | 175.09 (13) |
C1—C10—C9—C8 | 162.51 (14) | C10—C9—C11—C12 | −177.79 (13) |
C1—C10—C9—C11 | 36.89 (16) | C10—C9—C11—H11B | −57 (12) |
C1—C10—C9—H9 | −81 (3) | C10—C9—C11—H11A | 61 (3) |
C1—C10—C5—C6 | −178.07 (11) | C11—C9—C8—C14 | −57.82 (14) |
C1—C10—C5—C4 | −0.86 (13) | C11—C12—C13—C17 | 168.36 (15) |
C1—C2—C3—C4 | −2.10 (13) | C11—C12—C13—C14 | 55.42 (15) |
H1—C1—C10—C9 | −3 (2) | C11—C12—C13—C18 | −71.24 (15) |
H1—C1—C10—C5 | −179.94 (19) | H11A—C11—C12—C13 | 67 (3) |
H1—C1—C2—C3 | −178.6 (3) | H11A—C11—C12—H12B | −53 (9) |
H1—C1—C2—H2 | 1 (9) | H11A—C11—C12—H12A | −172 (7) |
C2—C3—C4—C5 | 2.01 (13) | H11B—C11—C12—C13 | −175.5 (10) |
C2—C3—C4—H4 | −178.4 (4) | H11B—C11—C12—H12B | 64 (6) |
C2—C1—C10—C9 | 177.83 (5) | H11B—C11—C12—H12A | −55 (7) |
C2—C1—C10—C5 | 0.76 (13) | C12—C13—C17—C16 | −147.1 (3) |
H2—C2—C3—C4 | 178.4 (4) | C12—C13—C14—C15 | 165.61 (14) |
H2—C2—C1—C10 | −180 (1) | C12—C13—C14—H14 | 54 (4) |
C3—C4—C5—C10 | −0.51 (13) | C12—C13—C18—H18A | 177 (1) |
C3—C4—C5—C6 | 176.84 (10) | C12—C13—C18—H18B | 57 (7) |
C3—C2—C1—C10 | 0.71 (13) | C12—C13—C18—H18C | −62 (3) |
C4—C5—C10—C9 | −177.94 (5) | H12A—C12—C13—C17 | 47 (3) |
C4—C5—C6—C7 | 165.44 (14) | H12A—C12—C13—C14 | −66 (6) |
C4—C5—C6—H6A | 44 (4) | H12A—C12—C13—C18 | 168 (2) |
C4—C5—C6—H6B | −73 (2) | H12B—C12—C13—C17 | −71 (3) |
H4—C4—C5—C10 | 179.86 (11) | H12B—C12—C13—C14 | 175.9 (9) |
H4—C4—C5—C6 | −3 (2) | H12B—C12—C13—C18 | 49 (6) |
C5—C10—C9—C8 | −20.50 (16) | C13—C17—C16—C15 | 5.03 (14) |
C5—C10—C9—C11 | −146.1 (3) | C13—C17—C16—H16A | −115 (13) |
C5—C10—C9—H9 | 96 (4) | C13—C17—C16—H16B | 125 (5) |
C5—C6—C7—C8 | 44.91 (16) | C13—C14—C15—C16 | −39.91 (19) |
C5—C6—C7—H7 | 164 (3) | C13—C14—C15—H15A | −159 (18) |
C6—C7—C8—C14 | 175.79 (15) | C13—C14—C15—H15B | 79 (3) |
C6—C7—C8—C9 | −62.21 (13) | C14—C13—C17—C16 | −28.9 (2) |
C6—C7—C8—H8 | 56 (3) | C14—C13—C18—H18A | 53 (6) |
C6—C5—C10—C9 | 4.85 (12) | C14—C13—C18—H18B | −68 (4) |
H6A—C6—C7—C8 | 166 (2) | C14—C13—C18—H18C | 173 (2) |
H6A—C6—C7—H7 | −75 (6) | C14—C15—C16—C17 | 21.2 (2) |
H6A—C6—C5—C10 | −139 (7) | C14—C15—C16—H16A | 141 (14) |
H6B—C6—C7—C8 | −77 (6) | C14—C15—C16—H16B | −98 (3) |
H6B—C6—C7—H7 | 42 (7) | H14—C14—C13—C17 | −69 (3) |
H6B—C6—C5—C10 | 104 (5) | H14—C14—C13—C18 | 179 (2) |
C7—C8—C14—C13 | −174.06 (14) | H14—C14—C15—C16 | 72 (3) |
C7—C8—C14—C15 | −50.22 (15) | H14—C14—C15—H15A | −47 (9) |
C7—C8—C14—H14 | 71 (6) | H14—C14—C15—H15B | −169 (6) |
C7—C8—C9—C10 | 49.36 (15) | C15—C14—C13—C17 | 42.47 (17) |
C7—C8—C9—C11 | 176.45 (14) | C15—C14—C13—C18 | −68.59 (15) |
C7—C8—C9—H9 | −67 (6) | H15A—C15—C16—C17 | 140 (9) |
C7—C6—C5—C10 | −17.27 (12) | H15A—C15—C16—H16A | −100 (5) |
H7—C7—C8—C14 | 57 (12) | H15A—C15—C16—H16B | 20 (12) |
H7—C7—C8—C9 | 179 (2) | H15B—C15—C16—C17 | −97 (4) |
H7—C7—C8—H8 | −62 (5) | H15B—C15—C16—H16A | 22 (10) |
C8—C14—C13—C17 | 175.43 (14) | H15B—C15—C16—H16B | 143 (11) |
C8—C14—C13—C12 | −61.43 (13) | C16—C17—C13—C18 | 88.77 (15) |
C8—C14—C13—C18 | 64.37 (15) | C17—C13—C18—H18A | −56 (13) |
C8—C14—C15—C16 | −166.96 (14) | C17—C13—C18—H18B | −176 (2) |
C8—C14—C15—H15A | 74 (2) | C17—C13—C18—H18C | 65 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O1W | 0.87 | 1.82 | 2.673 (2) | 167 |
C2—H2···O1W | 1.08 | 2.62 | 3.354 (2) | 125 |
C8—H8···C18 | 1.10 | 2.67 | 3.106 (3) | 103 |
C18—H18A···C15 | 1.08 | 2.64 | 3.021 (3) | 100 |
O1W—H1W···O3i | 0.85 | 1.97 | 2.805 (2) | 167 |
O1W—H1W···C17i | 0.85 | 2.69 | 3.492 (2) | 158 |
O2—H2A···O1ii | 0.91 | 1.96 | 2.857 (2) | 169 |
O2—H2A···C3ii | 0.91 | 2.73 | 3.533 (3) | 148 |
C6—H6A···C2ii | 1.09 | 2.60 | 3.594 (3) | 151 |
C6—H6A···C3ii | 1.09 | 2.46 | 3.484 (3) | 156 |
O1W—H2W···O2iii | 0.91 | 1.85 | 2.758 (2) | 176 |
C2—H2···O2iii | 1.08 | 2.51 | 3.581 (3) | 170 |
C16—H16B···O3iv | 1.09 | 2.45 | 3.354 (3) | 139 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, y+1/2, −z+1; (iii) −x+2, y−1/2, −z+1; (iv) −x+2, y+1/2, −z. |
3,7
α-Dihydroxyestra-1,3,5(10)-trien-17-one monohydrate (ELMAM2_MoPro)
top
Crystal data top
C18H22O3·H2O | F(000) = 328 |
Mr = 304.37 | Dx = 1.315 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2yb | Cell parameters from 2931 reflections |
a = 6.143 (3) Å | θ = 3.0–72.2° |
b = 8.4833 (17) Å | µ = 0.74 mm−1 |
c = 14.767 (3) Å | T = 100 K |
β = 91.94 (2)° | Block, colorless |
V = 769.2 (4) Å3 | 0.46 × 0.22 × 0.12 mm |
Z = 2 | |
Data collection top
Bruker D8 Venture PHOTON II Detector diffractometer | 2931 independent reflections |
Radiation source: Microfocus | 2905 reflections with > 2.0σ(I) |
Graphite monochromator | Rint = 0.043 |
ω and phi scan | θmax = 72.2°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = 0→7 |
Tmin = 0.727, Tmax = 0.916 | k = −10→10 |
9196 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.088 | H-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 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.66934 (14) | 0.5271 (6) | 0.69518 (5) | 0.01249 (14) | |
H1A | 0.78728 | 0.48787 | 0.73396 | 0.02703 | |
O2 | 0.65437 (13) | 0.7914 (6) | 0.27769 (6) | 0.01295 (14) | |
H2A | 0.56171 | 0.88335 | 0.29040 | 0.02693 | |
O1W | 0.96343 (14) | 0.3775 (6) | 0.80181 (6) | 0.01836 (16) | |
H1W | 0.98485 | 0.37473 | 0.86647 | 0.03779 | |
H2W | 1.10074 | 0.34539 | 0.77855 | 0.03638 | |
O3 | 1.01932 (17) | 0.3342 (6) | −0.01049 (6) | 0.02196 (18) | |
C1 | 0.95933 (19) | 0.4396 (6) | 0.48704 (8) | 0.01045 (18) | |
H1 | 1.10790 | 0.38308 | 0.46660 | 0.02779 | |
C2 | 0.91906 (19) | 0.4515 (6) | 0.57890 (8) | 0.01165 (18) | |
H2 | 1.03592 | 0.40638 | 0.62899 | 0.02932 | |
C3 | 0.72546 (19) | 0.5206 (6) | 0.60582 (8) | 0.01016 (18) | |
C4 | 0.57842 (19) | 0.5805 (6) | 0.54090 (8) | 0.01125 (18) | |
H4 | 0.42972 | 0.63616 | 0.56191 | 0.02804 | |
C5 | 0.61985 (18) | 0.5686 (6) | 0.44846 (8) | 0.00959 (18) | |
C6 | 0.44667 (18) | 0.6297 (6) | 0.38192 (8) | 0.01110 (18) | |
H6A | 0.38771 | 0.74265 | 0.40678 | 0.02937 | |
H6B | 0.31014 | 0.54726 | 0.38075 | 0.02862 | |
C7 | 0.52304 (18) | 0.6516 (6) | 0.28552 (8) | 0.00955 (18) | |
H7 | 0.37942 | 0.66095 | 0.23940 | 0.02545 | |
C8 | 0.65512 (18) | 0.5084 (6) | 0.25817 (7) | 0.00876 (17) | |
H8 | 0.55387 | 0.40286 | 0.26620 | 0.02337 | |
C9 | 0.86237 (18) | 0.4879 (6) | 0.31961 (8) | 0.00877 (17) | |
H9 | 0.97100 | 0.58709 | 0.30536 | 0.02281 | |
C10 | 0.81158 (18) | 0.4968 (6) | 0.41997 (8) | 0.00865 (17) | |
C11 | 0.98469 (19) | 0.3368 (6) | 0.29441 (8) | 0.01118 (19) | |
H11A | 0.88480 | 0.23425 | 0.30958 | 0.02872 | |
H11B | 1.13422 | 0.32752 | 0.33621 | 0.02925 | |
C12 | 1.04240 (19) | 0.3314 (6) | 0.19371 (8) | 0.01138 (19) | |
H12A | 1.16232 | 0.42251 | 0.17980 | 0.03017 | |
H12B | 1.11403 | 0.21712 | 0.17828 | 0.03286 | |
C13 | 0.83842 (19) | 0.3569 (6) | 0.13365 (8) | 0.01037 (19) | |
C14 | 0.72626 (18) | 0.5124 (6) | 0.16002 (8) | 0.00954 (18) | |
H14 | 0.85241 | 0.60391 | 0.15702 | 0.02364 | |
C15 | 0.5634 (2) | 0.5455 (6) | 0.08096 (8) | 0.01324 (19) | |
H15A | 0.51819 | 0.66995 | 0.07825 | 0.03038 | |
H15B | 0.41742 | 0.47303 | 0.08606 | 0.03153 | |
C16 | 0.69493 (19) | 0.4977 (6) | −0.00228 (8) | 0.01307 (19) | |
H16A | 0.59085 | 0.43715 | −0.05261 | 0.03449 | |
H16B | 0.76674 | 0.60091 | −0.03380 | 0.03202 | |
C17 | 0.8726 (2) | 0.3874 (6) | 0.03400 (8) | 0.0127 (2) | |
C18 | 0.6848 (2) | 0.2130 (6) | 0.13507 (8) | 0.0159 (2) | |
H18A | 0.53899 | 0.23603 | 0.09467 | 0.03948 | |
H18B | 0.64203 | 0.18746 | 0.20368 | 0.03737 | |
H18C | 0.76569 | 0.11131 | 0.10834 | 0.04153 | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0154 (4) | 0.0115 (5) | 0.0105 (4) | −0.0019 (3) | −0.0020 (3) | −0.0012 (3) |
H1A | 0.02706 | 0.03136 | 0.02233 | 0.00451 | −0.00430 | 0.00016 |
O2 | 0.0129 (4) | 0.0078 (4) | 0.0182 (4) | 0.0008 (3) | 0.0005 (3) | 0.0012 (3) |
H2A | 0.03105 | 0.01544 | 0.03446 | 0.00548 | 0.00326 | 0.00141 |
O1W | 0.0189 (4) | 0.0230 (5) | 0.0131 (4) | 0.0065 (4) | −0.0017 (3) | 0.0018 (4) |
H1W | 0.04395 | 0.05082 | 0.01821 | 0.00667 | −0.00468 | 0.00094 |
H2W | 0.02978 | 0.04780 | 0.03155 | 0.01047 | 0.00111 | −0.00082 |
O3 | 0.0273 (5) | 0.0277 (6) | 0.0109 (4) | 0.0161 (4) | 0.0013 (3) | 0.0016 (4) |
C1 | 0.0102 (5) | 0.0108 (6) | 0.0101 (5) | 0.0025 (4) | −0.0034 (4) | 0.0001 (4) |
H1 | 0.02197 | 0.03414 | 0.02717 | 0.00888 | −0.00037 | −0.00007 |
C2 | 0.0113 (5) | 0.0122 (6) | 0.0112 (5) | 0.0017 (4) | −0.0039 (4) | 0.0006 (5) |
H2 | 0.02675 | 0.03748 | 0.02314 | 0.00692 | −0.00765 | 0.00240 |
C3 | 0.0129 (5) | 0.0078 (6) | 0.0096 (5) | −0.0008 (5) | −0.0022 (4) | −0.0005 (4) |
C4 | 0.0124 (5) | 0.0092 (5) | 0.0120 (5) | 0.0019 (5) | −0.0021 (4) | −0.0008 (5) |
H4 | 0.02474 | 0.03053 | 0.02896 | 0.00864 | 0.00237 | −0.00087 |
C5 | 0.0099 (5) | 0.0069 (6) | 0.0117 (5) | 0.0016 (5) | −0.0029 (4) | 0.0000 (4) |
C6 | 0.0096 (5) | 0.0109 (6) | 0.0126 (5) | 0.0029 (4) | −0.0017 (4) | 0.0019 (4) |
H6A | 0.03667 | 0.02074 | 0.03065 | 0.00916 | 0.00047 | −0.00151 |
H6B | 0.02316 | 0.03043 | 0.03196 | −0.00917 | −0.00359 | 0.00363 |
C7 | 0.0090 (5) | 0.0077 (6) | 0.0117 (5) | 0.0013 (5) | −0.0024 (4) | 0.0014 (4) |
H7 | 0.02021 | 0.02912 | 0.02652 | 0.00301 | −0.00676 | 0.00291 |
C8 | 0.0088 (5) | 0.0084 (5) | 0.0088 (5) | 0.0011 (5) | −0.0042 (4) | 0.0001 (5) |
H8 | 0.02430 | 0.01689 | 0.02868 | −0.00739 | −0.00288 | 0.00072 |
C9 | 0.0090 (5) | 0.0075 (6) | 0.0096 (5) | 0.0023 (4) | −0.0033 (4) | 0.0003 (4) |
H9 | 0.02167 | 0.01778 | 0.02886 | −0.00632 | −0.00097 | 0.00246 |
C10 | 0.0085 (5) | 0.0082 (5) | 0.0091 (5) | 0.0017 (4) | −0.0028 (4) | −0.0001 (5) |
C11 | 0.0146 (5) | 0.0089 (6) | 0.0098 (5) | 0.0039 (5) | −0.0038 (4) | 0.0008 (4) |
H11A | 0.03655 | 0.01767 | 0.03204 | −0.00378 | 0.00287 | −0.00013 |
H11B | 0.02460 | 0.03568 | 0.02691 | 0.00779 | −0.00750 | −0.00081 |
C12 | 0.0134 (5) | 0.0102 (6) | 0.0103 (5) | 0.0041 (5) | −0.0027 (4) | −0.0003 (4) |
H12A | 0.02907 | 0.03178 | 0.02948 | −0.00280 | −0.00150 | 0.00574 |
H12B | 0.04432 | 0.02512 | 0.02894 | 0.01663 | −0.00201 | −0.00150 |
C13 | 0.0130 (5) | 0.0078 (6) | 0.0100 (5) | 0.0019 (5) | −0.0039 (4) | 0.0005 (4) |
C14 | 0.0108 (5) | 0.0067 (6) | 0.0109 (5) | 0.0017 (4) | −0.0037 (4) | 0.0005 (4) |
H14 | 0.02192 | 0.01980 | 0.02905 | −0.00377 | −0.00134 | 0.00257 |
C15 | 0.0139 (5) | 0.0149 (6) | 0.0106 (5) | 0.0050 (5) | −0.0040 (4) | 0.0018 (4) |
H15A | 0.03665 | 0.02393 | 0.03029 | 0.00882 | −0.00279 | 0.00352 |
H15B | 0.02636 | 0.03797 | 0.02990 | −0.00855 | −0.00436 | 0.00059 |
C16 | 0.0156 (5) | 0.0124 (6) | 0.0109 (5) | 0.0031 (5) | −0.0044 (4) | 0.0015 (5) |
H16A | 0.03392 | 0.04041 | 0.02838 | 0.00303 | −0.00994 | −0.00706 |
H16B | 0.03317 | 0.02901 | 0.03405 | 0.00454 | 0.00353 | 0.00855 |
C17 | 0.0174 (6) | 0.0104 (6) | 0.0101 (5) | 0.0049 (5) | −0.0038 (4) | 0.0013 (5) |
C18 | 0.0229 (7) | 0.0089 (6) | 0.0154 (5) | −0.0025 (5) | −0.0049 (4) | −0.0017 (5) |
H18A | 0.03997 | 0.03535 | 0.04182 | −0.00483 | −0.01769 | 0.00351 |
H18B | 0.05575 | 0.03369 | 0.02263 | −0.01254 | 0.00065 | −0.00135 |
H18C | 0.05443 | 0.02297 | 0.04739 | 0.00447 | 0.00474 | −0.01130 |
Geometric parameters (Å, º) top
O1—C3 | 1.3762 (14) | C8—H8 | 1.0990 |
O1—H1A | 0.9671 | C9—C10 | 1.5266 (14) |
O2—C7 | 1.4414 (15) | C9—C11 | 1.5379 (17) |
O2—H2A | 0.9873 | C9—H9 | 1.0990 |
O1W—H1W | 0.9597 | C11—C12 | 1.5411 (15) |
O1W—H2W | 0.9609 | C11—H11B | 1.0920 |
O3—C17 | 1.2200 (18) | C11—H11A | 1.0920 |
C1—C10 | 1.4067 (17) | C12—C13 | 1.5259 (17) |
C1—C2 | 1.3907 (16) | C12—H12A | 1.0920 |
C1—H1 | 1.0830 | C12—H12B | 1.0920 |
C2—C3 | 1.3960 (18) | C13—C17 | 1.5157 (15) |
C2—H2 | 1.0830 | C13—C14 | 1.5443 (17) |
C3—C4 | 1.3910 (17) | C13—C18 | 1.5440 (18) |
C4—C5 | 1.4007 (16) | C14—C15 | 1.5374 (16) |
C4—H4 | 1.0830 | C14—H14 | 1.0990 |
C5—C10 | 1.4032 (18) | C15—C16 | 1.5479 (17) |
C5—C6 | 1.5152 (16) | C15—H15A | 1.0920 |
C6—C7 | 1.5251 (16) | C15—H15B | 1.0920 |
C6—H6A | 1.0920 | C16—C17 | 1.5207 (18) |
C6—H6B | 1.0920 | C16—H16A | 1.0920 |
C7—C8 | 1.5229 (17) | C16—H16B | 1.0920 |
C7—H7 | 1.0990 | C18—H18A | 1.0770 |
C8—C14 | 1.5283 (14) | C18—H18B | 1.0770 |
C8—C9 | 1.5480 (16) | C18—H18C | 1.0770 |
| | | |
C3—O1—H1A | 110.298 | C9—C11—C12 | 112.85 (9) |
C7—O2—H2A | 107.872 | C9—C11—H11B | 109.377 |
H1W—O1W—H2W | 104.856 | C9—C11—H11A | 109.363 |
C10—C1—C2 | 122.00 (10) | C12—C11—H11B | 109.058 |
C10—C1—H1 | 119.091 | C12—C11—H11A | 108.890 |
C2—C1—H1 | 118.906 | H11B—C11—H11A | 107.138 |
C3—C2—C1 | 119.32 (10) | C13—C12—C11 | 110.21 (9) |
C3—C2—H2 | 120.357 | C13—C12—H12A | 109.660 |
C1—C2—H2 | 120.322 | C13—C12—H12B | 109.472 |
O1—C3—C4 | 117.93 (9) | C11—C12—H12A | 109.839 |
O1—C3—C2 | 122.23 (9) | C11—C12—H12B | 109.577 |
C4—C3—C2 | 119.79 (10) | H12A—C12—H12B | 108.052 |
C3—C4—C5 | 120.67 (10) | C17—C13—C14 | 100.16 (9) |
C3—C4—H4 | 119.743 | C17—C13—C12 | 116.78 (8) |
C5—C4—H4 | 119.590 | C17—C13—C18 | 104.67 (9) |
C10—C5—C6 | 122.16 (10) | C14—C13—C12 | 109.83 (9) |
C10—C5—C4 | 120.38 (10) | C14—C13—C18 | 113.19 (10) |
C6—C5—C4 | 117.41 (9) | C12—C13—C18 | 111.75 (10) |
C7—C6—C5 | 114.55 (9) | C13—C14—C8 | 111.38 (9) |
C7—C6—H6A | 108.858 | C13—C14—C15 | 104.43 (9) |
C7—C6—H6B | 108.875 | C13—C14—H14 | 105.785 |
C5—C6—H6A | 108.426 | C8—C14—C15 | 121.63 (8) |
C5—C6—H6B | 108.230 | C8—C14—H14 | 106.174 |
H6A—C6—H6B | 107.698 | C15—C14—H14 | 106.377 |
O2—C7—C8 | 109.29 (9) | C14—C15—C16 | 102.19 (9) |
O2—C7—C6 | 111.45 (9) | C14—C15—H15A | 111.263 |
O2—C7—H7 | 109.308 | C14—C15—H15B | 111.075 |
C8—C7—C6 | 109.52 (9) | C16—C15—H15A | 111.309 |
C8—C7—H7 | 108.486 | C16—C15—H15B | 111.045 |
C6—C7—H7 | 108.737 | H15A—C15—H15B | 109.785 |
C7—C8—C14 | 113.95 (9) | C17—C16—C15 | 105.62 (10) |
C7—C8—C9 | 111.68 (9) | C17—C16—H16A | 110.326 |
C7—C8—H8 | 108.212 | C17—C16—H16B | 110.355 |
C14—C8—C9 | 107.60 (8) | C15—C16—H16A | 110.752 |
C14—C8—H8 | 107.547 | C15—C16—H16B | 110.948 |
C9—C8—H8 | 107.599 | H16A—C16—H16B | 108.823 |
C8—C9—C10 | 111.86 (9) | O3—C17—C13 | 126.06 (10) |
C8—C9—C11 | 110.54 (9) | O3—C17—C16 | 124.92 (10) |
C8—C9—H9 | 107.113 | C13—C17—C16 | 109.02 (9) |
C10—C9—C11 | 113.19 (8) | C13—C18—H18A | 110.242 |
C10—C9—H9 | 107.065 | C13—C18—H18B | 109.893 |
C11—C9—H9 | 106.688 | C13—C18—H18C | 109.759 |
C9—C10—C5 | 120.92 (9) | H18A—C18—H18B | 109.445 |
C9—C10—C1 | 121.21 (9) | H18A—C18—H18C | 109.152 |
C5—C10—C1 | 117.82 (10) | H18B—C18—H18C | 108.316 |
| | | |
O1—C3—C4—C5 | −176.00 (16) | C8—C14—C15—H15B | −48.32 |
O1—C3—C4—H4 | 3.49 | C8—C9—C11—C12 | 55.64 (17) |
O1—C3—C2—C1 | 175.81 (17) | C8—C9—C11—H11B | 177.23 |
O1—C3—C2—H2 | −3.52 | C8—C9—C11—H11A | −65.72 |
H1A—O1—C3—C4 | −176.65 | H8—C8—C14—C13 | −54.18 |
H1A—O1—C3—C2 | 5.73 | H8—C8—C14—C15 | 69.56 |
O2—C7—C8—C14 | −61.83 (18) | H8—C8—C14—H14 | −168.87 |
O2—C7—C8—C9 | 60.35 (18) | H8—C8—C9—C10 | −69.34 |
O2—C7—C8—H8 | 178.60 | H8—C8—C9—C11 | 57.77 |
O2—C7—C6—C5 | −76.29 (17) | H8—C8—C9—H9 | 173.64 |
O2—C7—C6—H6A | 45.25 | C9—C8—C14—C13 | 61.48 (18) |
O2—C7—C6—H6B | 162.40 | C9—C8—C14—C15 | −174.78 (17) |
H2A—O2—C7—C8 | 175.02 | C9—C8—C14—H14 | −53.21 |
H2A—O2—C7—C6 | −63.79 | C9—C11—C12—C13 | −53.86 (19) |
H2A—O2—C7—H7 | 56.43 | C9—C11—C12—H12A | 67.06 |
O3—C17—C13—C14 | 150.5 (3) | C9—C11—C12—H12B | −174.39 |
O3—C17—C13—C12 | 32.0 (2) | H9—C9—C8—C14 | 58.01 |
O3—C17—C13—C18 | −92.1 (2) | H9—C9—C11—C12 | −60.49 |
O3—C17—C16—C15 | −174.29 (15) | H9—C9—C11—H11B | 61.10 |
O3—C17—C16—H16A | 65.98 | H9—C9—C11—H11A | 178.15 |
O3—C17—C16—H16B | −54.31 | C10—C9—C8—C14 | 175.03 (17) |
C1—C10—C9—C8 | 162.4 (5) | C10—C9—C11—C12 | −177.98 (16) |
C1—C10—C9—C11 | 36.8 (2) | C10—C9—C11—H11B | −56.39 |
C1—C10—C9—H9 | −80.52 | C10—C9—C11—H11A | 60.65 |
C1—C10—C5—C6 | −178.13 (14) | C11—C9—C8—C14 | −57.85 (18) |
C1—C10—C5—C4 | −0.63 (16) | C11—C12—C13—C17 | 168.2 (6) |
C1—C2—C3—C4 | −1.77 (16) | C11—C12—C13—C14 | 55.12 (19) |
H1—C1—C10—C9 | −3.10 | C11—C12—C13—C18 | −71.36 (18) |
H1—C1—C10—C5 | 179.61 | H11A—C11—C12—C13 | 67.77 |
H1—C1—C2—C3 | −178.41 | H11A—C11—C12—H12A | −171.31 |
H1—C1—C2—H2 | 0.92 | H11A—C11—C12—H12B | −52.75 |
C2—C3—C4—C5 | 1.68 (16) | H11B—C11—C12—C13 | −175.63 |
C2—C3—C4—H4 | −178.83 | H11B—C11—C12—H12A | −54.71 |
C2—C1—C10—C9 | 177.82 (6) | H11B—C11—C12—H12B | 63.84 |
C2—C1—C10—C5 | 0.52 (16) | C12—C13—C17—C16 | −147.3 (3) |
H2—C2—C3—C4 | 178.90 | C12—C13—C14—C15 | 165.8 (7) |
H2—C2—C1—C10 | −180.00 | C12—C13—C14—H14 | 53.76 |
C3—C4—C5—C10 | −0.47 (16) | C12—C13—C18—H18A | 177.40 |
C3—C4—C5—C6 | 177.15 (12) | C12—C13—C18—H18B | 56.69 |
C3—C2—C1—C10 | 0.67 (16) | C12—C13—C18—H18C | −62.33 |
C4—C5—C10—C9 | −177.93 (6) | H12A—C12—C13—C17 | 47.16 |
C4—C5—C6—C7 | 165.4 (7) | H12A—C12—C13—C14 | −65.91 |
C4—C5—C6—H6A | 43.59 | H12A—C12—C13—C18 | 167.61 |
C4—C5—C6—H6B | −72.97 | H12B—C12—C13—C17 | −71.22 |
H4—C4—C5—C10 | −179.96 | H12B—C12—C13—C14 | 175.71 |
H4—C4—C5—C6 | −2.34 | H12B—C12—C13—C18 | 49.23 |
C5—C10—C9—C8 | −20.4 (2) | C13—C17—C16—C15 | 5.06 (18) |
C5—C10—C9—C11 | −146.0 (4) | C13—C17—C16—H16A | −114.67 |
C5—C10—C9—H9 | 96.69 | C13—C17—C16—H16B | 125.04 |
C5—C6—C7—C8 | 44.8 (2) | C13—C14—C15—C16 | −39.9 (2) |
C5—C6—C7—H7 | 163.15 | C13—C14—C15—H15A | −158.78 |
C6—C7—C8—C14 | 175.82 (19) | C13—C14—C15—H15B | 78.59 |
C6—C7—C8—C9 | −61.99 (16) | C14—C13—C17—C16 | −28.9 (3) |
C6—C7—C8—H8 | 56.25 | C14—C13—C18—H18A | 52.78 |
C6—C5—C10—C9 | 4.57 (14) | C14—C13—C18—H18B | −67.93 |
H6A—C6—C7—C8 | 166.31 | C14—C13—C18—H18C | 173.05 |
H6A—C6—C7—H7 | −75.30 | C14—C15—C16—C17 | 21.2 (3) |
H6A—C6—C5—C10 | −138.84 | C14—C15—C16—H16A | 140.67 |
H6B—C6—C7—C8 | −76.55 | C14—C15—C16—H16B | −98.37 |
H6B—C6—C7—H7 | 41.85 | H14—C14—C13—C17 | −69.68 |
H6B—C6—C5—C10 | 104.61 | H14—C14—C13—C18 | 179.42 |
C7—C8—C14—C13 | −174.12 (17) | H14—C14—C15—C16 | 71.72 |
C7—C8—C14—C15 | −50.38 (19) | H14—C14—C15—H15A | −47.16 |
C7—C8—C14—H14 | 71.19 | H14—C14—C15—H15B | −169.79 |
C7—C8—C9—C10 | 49.27 (19) | C15—C14—C13—C17 | 42.4 (2) |
C7—C8—C9—C11 | 176.38 (17) | C15—C14—C13—C18 | −68.54 (19) |
C7—C8—C9—H9 | −67.75 | H15A—C15—C16—C17 | 140.07 |
C7—C6—C5—C10 | −17.1 (2) | H15A—C15—C16—H16A | −100.48 |
H7—C7—C8—C14 | 57.27 | H15A—C15—C16—H16B | 20.48 |
H7—C7—C8—C9 | 179.46 | H15B—C15—C16—C17 | −97.29 |
H7—C7—C8—H8 | −62.30 | H15B—C15—C16—H16A | 22.16 |
C8—C14—C13—C17 | 175.39 (17) | H15B—C15—C16—H16B | 143.12 |
C8—C14—C13—C12 | −61.17 (17) | C16—C17—C13—C18 | 88.54 (19) |
C8—C14—C13—C18 | 64.49 (18) | C17—C13—C18—H18A | −55.31 |
C8—C14—C15—C16 | −166.8 (4) | C17—C13—C18—H18B | −176.02 |
C8—C14—C15—H15A | 74.31 | C17—C13—C18—H18C | 64.96 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O1W | 0.97 | 1.73 | 2.6761 (17) | 167 |
C2—H2···O1W | 1.08 | 2.62 | 3.3530 (16) | 125 |
C8—H8···C18 | 1.10 | 2.66 | 3.1051 (19) | 103 |
C18—H18A···C15 | 1.08 | 2.64 | 3.019 (2) | 100 |
O1W—H1W···O3i | 0.96 | 1.85 | 2.8054 (14) | 171 |
O1W—H1W···C17i | 0.96 | 2.59 | 3.4934 (17) | 156 |
O2—H2A···O1ii | 0.99 | 1.89 | 2.8576 (17) | 166 |
O2—H2A···C3ii | 0.99 | 2.65 | 3.529 (2) | 149 |
C6—H6A···C2ii | 1.09 | 2.60 | 3.595 (2) | 151 |
C6—H6A···C3ii | 1.09 | 2.46 | 3.487 (2) | 156 |
O1W—H2W···O2iii | 0.96 | 1.80 | 2.7589 (17) | 173 |
C2—H2···O2iii | 1.08 | 2.51 | 3.580 (2) | 170 |
C16—H16B···O3iv | 1.09 | 2.45 | 3.354 (2) | 139 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, y+1/2, −z+1; (iii) −x+2, y−1/2, −z+1; (iv) −x+2, y+1/2, −z. |