#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/22/8102222.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102222
loop_
_publ_author_name
'Wefelscheid, Ulrike K.'
'Brüdgam, Irene'
'Hartl, Hans'
'Reißig, Hans-Ulrich'
_publ_section_title
;
Crystal structure of (8S*,9S*,13S*,14R*,17S*)-estra-1(10),2,4,6-tetraene-
14,17-diol monohydrate, C₁₈H₂₂O₂ · H₂O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              467
_journal_page_last               468
_journal_volume                  222
_journal_year                    2007
_chemical_formula_structural     'C18H22O2 &#x00B7; H2O'
_chemical_formula_sum            'C18 H24 O3'
_chemical_formula_weight         288.38
_chemical_melting_point          441.0(10)
_chemical_name_systematic
; 
(8S*,9S*,13S*,14R*,17S*)-estra-1(10),2,4,6-tetraene-14,17-diol monohydrate
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9945(19)
_cell_length_b                   17.309(3)
_cell_length_c                   7.4999(12)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      3.41
_cell_volume                     1557.1(4)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'phi/omega, δω = 0.3°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17353
_diffrn_reflns_theta_full        30.59
_diffrn_reflns_theta_max         30.59
_diffrn_reflns_theta_min         2.07
_diffrn_standards_interval_time  '5 sec/frame'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          .6
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(9)
_refine_ls_extinction_coef       0.0000(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         4725
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          4.579
_refine_ls_shift/su_mean         0.023
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0672P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                3691
_reflns_number_total             4725
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2158.cff
_cod_data_source_block           org3wef
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '440 - 442K' was changed to
'441.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      Pca21
_cod_database_code               8102222
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.33930(9) 0.13777(6) 0.08574(13) 0.0296(2) Uani 1 4 a d . . .
H1 H 0.3306 0.1099 0.1763 0.044 Uiso 1 4 a calc R . .
O2 O 0.67651(9) 0.05636(6) 0.13245(15) 0.0349(3) Uani 1 4 a d . . .
H2 H 0.6834 0.0328 0.0352 0.052 Uiso 1 4 a calc R . .
C1 C 0.63044(16) 0.39270(9) 0.2264(3) 0.0433(4) Uani 1 4 a d . . .
H1A H 0.6915 0.3804 0.1509 0.052 Uiso 1 4 a calc R . .
C2 C 0.6486(2) 0.43673(9) 0.3797(3) 0.0564(6) Uani 1 4 a d . . .
H2A H 0.7214 0.4547 0.4072 0.068 Uiso 1 4 a calc R . .
C3 C 0.5604(2) 0.45420(10) 0.4914(3) 0.0643(7) Uani 1 4 a d . . .
H3 H 0.5729 0.4837 0.5963 0.077 Uiso 1 4 a calc R . .
C4 C 0.4547(2) 0.42906(10) 0.4509(3) 0.0521(5) Uani 1 4 a d . . .
H4 H 0.3946 0.4416 0.5281 0.063 Uiso 1 4 a calc R . .
C5 C 0.43462(15) 0.38529(8) 0.2977(2) 0.0374(4) Uani 1 4 a d . . .
C6 C 0.32305(15) 0.35751(9) 0.2554(2) 0.0366(4) Uani 1 4 a d . . .
H6 H 0.2608 0.3797 0.3146 0.044 Uiso 1 4 a calc R . .
C7 C 0.30613(13) 0.30203(9) 0.1362(2) 0.0321(3) Uani 1 4 a d . . .
H7 H 0.2323 0.2843 0.1159 0.038 Uiso 1 4 a calc R . .
C8 C 0.40040(11) 0.26638(8) 0.03236(19) 0.0257(3) Uani 1 4 a d . . .
H8 H 0.3709 0.2558 -0.0899 0.031 Uiso 1 4 a calc R . .
C9 C 0.49703(12) 0.32460(8) 0.0097(2) 0.0285(3) Uani 1 4 a d . . .
H9 H 0.4695 0.3650 -0.0749 0.034 Uiso 1 4 a calc R . .
C10 C 0.52467(13) 0.36671(8) 0.1828(2) 0.0315(3) Uani 1 4 a d . . .
C11 C 0.59623(13) 0.28549(8) -0.0828(2) 0.0326(3) Uani 1 4 a d . . .
H11A H 0.5755 0.2730 -0.2073 0.039 Uiso 1 4 a calc R . .
H11B H 0.6598 0.3219 -0.0863 0.039 Uiso 1 4 a calc R . .
C12 C 0.63231(12) 0.21168(8) 0.0118(2) 0.0291(3) Uani 1 4 a d . . .
H12A H 0.6556 0.2243 0.1350 0.035 Uiso 1 4 a calc R . .
H12B H 0.6974 0.1893 -0.0510 0.035 Uiso 1 4 a calc R . .
C13 C 0.53766(11) 0.15144(7) 0.01774(18) 0.0238(3) Uani 1 4 a d . . .
C14 C 0.43482(11) 0.18749(7) 0.11135(18) 0.0228(3) Uani 1 4 a d . . .
C15 C 0.46660(12) 0.18754(8) 0.31092(18) 0.0251(3) Uani 1 4 a d . . .
H15A H 0.3993 0.1818 0.3863 0.030 Uiso 1 4 a calc R . .
H15B H 0.5046 0.2363 0.3433 0.030 Uiso 1 4 a calc R . .
C16 C 0.54580(12) 0.11785(8) 0.33615(19) 0.0268(3) Uani 1 4 a d . . .
H16A H 0.6171 0.1346 0.3904 0.032 Uiso 1 4 a calc R . .
H16B H 0.5112 0.0784 0.4140 0.032 Uiso 1 4 a calc R . .
C17 C 0.56532(12) 0.08532(8) 0.14814(19) 0.0271(3) Uani 1 4 a d . . .
H17 H 0.5119 0.0419 0.1273 0.033 Uiso 1 4 a calc R . .
C18 C 0.51459(13) 0.12030(9) -0.1698(2) 0.0309(3) Uani 1 4 a d . . .
H18A H 0.5846 0.1030 -0.2239 0.046 Uiso 1 4 a calc R . .
H18B H 0.4818 0.1613 -0.2431 0.046 Uiso 1 4 a calc R . .
H18C H 0.4626 0.0767 -0.1623 0.046 Uiso 1 4 a calc R . .
O1W O 0.77416(9) 0.95719(6) 0.36000(15) 0.0291(2) Uani 1 4 a d . . .
H1W H 0.7361(18) 0.9283(10) 0.414(3) 0.041(5) Uiso 1 4 a d . . .
H2W H 0.7299(18) 0.9893(11) 0.302(3) 0.055(6) Uiso 1 4 a d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C1 C2 121.0(2) . . ?
C3 C2 C1 119.93(19) . . ?
C4 C3 C2 120.2(2) . . ?
C3 C4 C5 120.8(2) . . ?
C4 C5 C10 119.41(17) . . ?
C4 C5 C6 121.11(17) . . ?
C10 C5 C6 119.48(14) . . ?
C7 C6 C5 121.73(15) . . ?
C6 C7 C8 122.01(15) . . ?
C7 C8 C14 111.39(12) . . ?
C7 C8 C9 110.68(12) . . ?
C14 C8 C9 114.72(11) . . ?
C10 C9 C11 115.28(13) . . ?
C10 C9 C8 112.39(12) . . ?
C11 C9 C8 110.10(11) . . ?
C1 C10 C5 118.70(16) . . ?
C1 C10 C9 123.73(15) . . ?
C5 C10 C9 117.37(14) . . ?
C12 C11 C9 112.30(12) . . ?
C11 C12 C13 111.80(12) . . ?
C18 C13 C17 111.12(11) . . ?
C18 C13 C12 110.14(11) . . ?
C17 C13 C12 111.22(11) . . ?
C18 C13 C14 114.44(11) . . ?
C17 C13 C14 100.53(11) . . ?
C12 C13 C14 109.06(11) . . ?
O1 C14 C15 108.95(11) . . ?
O1 C14 C8 105.28(10) . . ?
C15 C14 C8 115.91(11) . . ?
O1 C14 C13 109.31(11) . . ?
C15 C14 C13 104.05(11) . . ?
C8 C14 C13 113.25(11) . . ?
C14 C15 C16 105.64(11) . . ?
C17 C16 C15 105.49(11) . . ?
O2 C17 C16 110.26(11) . . ?
O2 C17 C13 114.14(12) . . ?
C16 C17 C13 106.11(10) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C14 1.4458(17) . ?
O2 C17 1.4296(17) . ?
C1 C10 1.385(2) . ?
C1 C2 1.396(3) . ?
C2 C3 1.383(4) . ?
C3 C4 1.374(3) . ?
C4 C5 1.397(3) . ?
C5 C10 1.419(2) . ?
C5 C6 1.457(3) . ?
C6 C7 1.327(2) . ?
C7 C8 1.505(2) . ?
C8 C14 1.5448(18) . ?
C8 C9 1.545(2) . ?
C9 C10 1.525(2) . ?
C9 C11 1.535(2) . ?
C11 C12 1.524(2) . ?
C12 C13 1.5422(19) . ?
C13 C18 1.531(2) . ?
C13 C17 1.5415(19) . ?
C13 C14 1.5504(19) . ?
C14 C15 1.5445(19) . ?
C15 C16 1.5471(19) . ?
C16 C17 1.536(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1W 0.84 1.92 2.7465(15) 165.8 3_465
O2 H2 O1W 0.84 1.92 2.7334(15) 161.8 4_644
O1W H1W O1 0.79(2) 1.94(2) 2.7239(16) 169(2) 2_665
O1W H2W O2 0.88(2) 1.84(2) 2.6890(16) 161(2) 1_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C10 0.0(3) . . . . ?
C3 C4 C5 C6 179.12(17) . . . . ?
C4 C5 C6 C7 -164.14(16) . . . . ?
C10 C5 C6 C7 15.0(2) . . . . ?
C5 C6 C7 C8 -2.4(2) . . . . ?
C6 C7 C8 C14 100.76(16) . . . . ?
C6 C7 C8 C9 -28.14(19) . . . . ?
C7 C8 C9 C10 45.39(16) . . . . ?
C14 C8 C9 C10 -81.69(14) . . . . ?
C7 C8 C9 C11 175.37(12) . . . . ?
C14 C8 C9 C11 48.29(16) . . . . ?
C2 C1 C10 C5 -0.4(2) . . . . ?
C2 C1 C10 C9 174.38(14) . . . . ?
C4 C5 C10 C1 0.0(2) . . . . ?
C6 C5 C10 C1 -179.12(14) . . . . ?
C4 C5 C10 C9 -175.08(14) . . . . ?
C6 C5 C10 C9 5.8(2) . . . . ?
C11 C9 C10 C1 22.0(2) . . . . ?
C8 C9 C10 C1 149.30(14) . . . . ?
C11 C9 C10 C5 -163.15(12) . . . . ?
C8 C9 C10 C5 -35.87(17) . . . . ?
C10 C9 C11 C12 74.80(16) . . . . ?
C8 C9 C11 C12 -53.63(17) . . . . ?
C9 C11 C12 C13 60.24(17) . . . . ?
C11 C12 C13 C18 69.05(15) . . . . ?
C11 C12 C13 C17 -167.30(12) . . . . ?
C11 C12 C13 C14 -57.33(16) . . . . ?
C7 C8 C14 O1 65.07(15) . . . . ?
C9 C8 C14 O1 -168.22(11) . . . . ?
C7 C8 C14 C15 -55.39(16) . . . . ?
C9 C8 C14 C15 71.32(15) . . . . ?
C7 C8 C14 C13 -175.55(12) . . . . ?
C9 C8 C14 C13 -48.84(16) . . . . ?
C18 C13 C14 O1 44.61(15) . . . . ?
C17 C13 C14 O1 -74.53(12) . . . . ?
C12 C13 C14 O1 168.48(10) . . . . ?
C18 C13 C14 C15 160.87(11) . . . . ?
C17 C13 C14 C15 41.73(13) . . . . ?
C12 C13 C14 C15 -75.26(13) . . . . ?
C18 C13 C14 C8 -72.41(15) . . . . ?
C17 C13 C14 C8 168.44(11) . . . . ?
C12 C13 C14 C8 51.45(15) . . . . ?
O1 C14 C15 C16 86.93(12) . . . . ?
C8 C14 C15 C16 -154.61(11) . . . . ?
C13 C14 C15 C16 -29.58(14) . . . . ?
C14 C15 C16 C17 5.26(14) . . . . ?
C15 C16 C17 O2 145.35(11) . . . . ?
C15 C16 C17 C13 21.28(14) . . . . ?
C18 C13 C17 O2 77.95(15) . . . . ?
C12 C13 C17 O2 -45.14(15) . . . . ?
C14 C13 C17 O2 -160.52(11) . . . . ?
C18 C13 C17 C16 -160.43(12) . . . . ?
C12 C13 C17 C16 76.48(13) . . . . ?
C14 C13 C17 C16 -38.90(13) . . . . ?
