#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:12:01 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179561 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/30/4503074.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_4503074
loop_
_publ_author_name
'Guguta, C.'
'Eeuwijk, I.'
'Smits, J. M. M.'
'de Gelder, R.'
_publ_section_title
;
 Structural Diversity of Ethinyl Estradiol Solvates
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              823
_journal_paper_doi               10.1021/cg0702277
_journal_volume                  8
_journal_year                    2008
_chemical_formula_moiety         'C20 H24 O2, C H4 O'
_chemical_formula_sum            'C21 H28 O3'
_chemical_formula_weight         328.43
_chemical_name_common            'ethinyl estradiol methanolate'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-11-30
_audit_creation_method           'SHELXL, adapted and expanded'
_cell_angle_alpha                90.00
_cell_angle_beta                 106.090(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.6449(7)
_cell_length_b                   16.5425(14)
_cell_length_c                   8.6480(4)
_cell_measurement_reflns_used    96
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      27.490
_cell_measurement_theta_min      2.450
_cell_volume                     913.38(13)
_computing_data_collection
;
Nonius "Collect" program suite (Nonius, 1999)
;
_computing_data_reduction
;
Nonius "EvalCCD" program suite (Duisenberg, 1998)
;
_computing_molecular_graphics
;
PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
CRUNCH (de Gelder et al., 1993),
;
_diffrn_ambient_temperature      208(2)
_diffrn_detector_area_resol_mean 18.4
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'area detector φ and ω scan'
_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  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18784
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.45
_diffrn_standards_decay_%        0.000
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_correction_T_min  0.7929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS multiscan (Sheldrick, 1996)'
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rough fragment'
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_Flack   -1.0(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.037
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4190
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0412
_refine_ls_R_factor_obs          0.0412
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[σ²(Fo²)+(0.0420P)²+0.1459P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0877
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_obs         0.0828
_refine_ls_wR_factor_ref         0.0877
_reflns_number_gt                3503
_reflns_number_observed          3503
_reflns_number_total             4190
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0702277-file006.cif
_cod_data_source_block           eedmetoh
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (26
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (40 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4503074
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_calc_flag
_atom_site_refinement_flags
C1 C 1.1480(3) 0.28158(11) 1.1311(2) 0.0264(4) Uani 1 d .
H1 H 1.232(3) 0.2436(14) 1.095(2) 0.039(6) Uiso 1 d .
C2 C 1.2382(3) 0.32346(11) 1.2724(2) 0.0285(4) Uani 1 d .
H2 H 1.378(3) 0.3162(12) 1.329(2) 0.024(5) Uiso 1 d .
C3 C 1.1183(3) 0.37741(10) 1.3306(2) 0.0246(4) Uani 1 d .
O3 O 1.2085(2) 0.41675(7) 1.47342(15) 0.0303(3) Uani 1 d .
H3 H 1.116(4) 0.4270(16) 1.522(3) 0.055(8) Uiso 1 d .
C4 C 0.9131(3) 0.39114(10) 1.2441(2) 0.0255(4) Uani 1 d .
H4 H 0.828(3) 0.4301(12) 1.280(2) 0.023(5) Uiso 1 d .
C5 C 0.8238(3) 0.35089(10) 1.0995(2) 0.0230(4) Uani 1 d .
C6 C 0.6022(3) 0.37354(12) 1.0064(2) 0.0299(4) Uani 1 d .
H6A H 0.593(3) 0.4310(14) 1.002(2) 0.033(5) Uiso 1 d .
H6B H 0.513(3) 0.3533(14) 1.068(2) 0.035(5) Uiso 1 d .
C7 C 0.5316(3) 0.33675(11) 0.8389(2) 0.0269(4) Uani 1 d .
H7A H 0.593(3) 0.3655(13) 0.760(3) 0.035(5) Uiso 1 d .
H7B H 0.376(3) 0.3396(12) 0.794(2) 0.024(5) Uiso 1 d .
C8 C 0.6041(3) 0.24908(10) 0.84283(19) 0.0197(3) Uani 1 d .
H8 H 0.552(3) 0.2218(11) 0.928(2) 0.015(4) Uiso 1 d .
C9 C 0.8448(3) 0.24615(10) 0.8885(2) 0.0209(3) Uani 1 d .
H9 H 0.881(2) 0.2720(10) 0.8038(18) 0.004(3) Uiso 1 d .
C10 C 0.9399(3) 0.29295(9) 1.0432(2) 0.0216(4) Uani 1 d .
C11 C 0.9229(3) 0.15857(11) 0.8931(2) 0.0239(4) Uani 1 d .
H11A H 1.077(3) 0.1590(10) 0.9170(19) 0.013(4) Uiso 1 d .
H11B H 0.886(3) 0.1306(12) 0.984(2) 0.033(5) Uiso 1 d .
C12 C 0.8274(3) 0.11338(11) 0.7345(2) 0.0248(4) Uani 1 d .
H12A H 0.873(3) 0.1380(12) 0.647(2) 0.026(5) Uiso 1 d .
H12B H 0.871(3) 0.0574(13) 0.741(2) 0.033(5) Uiso 1 d .
C13 C 0.5878(2) 0.11720(10) 0.68789(19) 0.0217(4) Uani 1 d .
C14 C 0.5173(3) 0.20598(10) 0.6835(2) 0.0203(3) Uani 1 d .
H14 H 0.577(3) 0.2336(10) 0.607(2) 0.015(4) Uiso 1 d .
C15 C 0.2814(3) 0.20242(11) 0.6097(2) 0.0260(4) Uani 1 d .
H15A H 0.217(3) 0.2520(12) 0.561(2) 0.024(5) Uiso 1 d .
H15B H 0.206(3) 0.1918(11) 0.691(2) 0.025(5) Uiso 1 d .
C16 C 0.2493(3) 0.13243(12) 0.4878(2) 0.0286(4) Uani 1 d .
H16A H 0.199(3) 0.1499(12) 0.378(3) 0.031(5) Uiso 1 d .
H16B H 0.165(3) 0.0944(13) 0.505(2) 0.027(5) Uiso 1 d .
C17 C 0.4675(3) 0.09149(11) 0.5126(2) 0.0261(4) Uani 1 d .
O17 O 0.4366(2) 0.00632(8) 0.48886(17) 0.0351(3) Uani 1 d .
H17 H 0.553(4) -0.0175(16) 0.492(3) 0.056(8) Uiso 1 d .
C18 C 0.5064(3) 0.06508(12) 0.8047(2) 0.0314(4) Uani 1 d .
H18A H 0.570(3) 0.0832(13) 0.916(3) 0.040(6) Uiso 1 d .
H18B H 0.551(3) 0.0102(15) 0.800(2) 0.033(5) Uiso 1 d .
H18C H 0.351(4) 0.0642(13) 0.779(2) 0.035(5) Uiso 1 d .
C20 C 0.5725(3) 0.12400(13) 0.3956(2) 0.0313(4) Uani 1 d .
C21 C 0.6574(4) 0.15283(16) 0.3050(3) 0.0451(5) Uani 1 d .
H21 H 0.725(5) 0.1767(19) 0.228(4) 0.080(9) Uiso 1 d .
C25 C 1.0267(4) 0.47332(14) 0.8020(2) 0.0421(5) Uani 1 d .
H25A H 1.1139 0.5191 0.7927 0.063 Uiso 1 calc R
H25B H 1.1102 0.4338 0.8751 0.063 Uiso 1 calc R
H25C H 0.9127 0.4915 0.8433 0.063 Uiso 1 calc R
O26 O 0.9437(2) 0.43763(9) 0.64842(17) 0.0371(3) Uani 1 d .
H26 H 0.828(4) 0.4587(16) 0.612(3) 0.046(7) Uiso 1 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_publ_flag
C2 C1 C10 122.29(17) y
C3 C2 C1 119.43(17) y
O3 C3 C4 121.83(15) y
O3 C3 C2 118.72(16) y
C4 C3 C2 119.45(16) y
C3 C4 C5 121.22(16) y
C4 C5 C10 119.98(15) y
C4 C5 C6 117.84(15) y
C10 C5 C6 122.16(15) y
C5 C6 C7 113.85(15) y
C6 C7 C8 110.31(15) y
C14 C8 C7 112.86(14) y
C14 C8 C9 108.97(13) y
C7 C8 C9 109.58(13) y
C10 C9 C11 113.70(14) y
C10 C9 C8 110.98(13) y
C11 C9 C8 110.86(13) y
C1 C10 C5 117.49(15) y
C1 C10 C9 121.19(15) y
C5 C10 C9 121.28(15) y
C9 C11 C12 112.52(14) y
C13 C12 C11 110.92(14) y
C12 C13 C18 109.49(14) y
C12 C13 C14 109.44(13) y
C18 C13 C14 113.06(14) y
C12 C13 C17 117.30(13) y
C18 C13 C17 107.83(14) y
C14 C13 C17 99.53(13) y
C8 C14 C15 119.21(14) y
C8 C14 C13 112.96(13) y
C15 C14 C13 104.16(13) y
C14 C15 C16 104.32(14) y
C15 C16 C17 106.55(14) y
O17 C17 C20 109.61(15) y
O17 C17 C16 108.46(14) y
C20 C17 C16 110.12(15) y
O17 C17 C13 114.94(14) y
C20 C17 C13 110.66(14) y
C16 C17 C13 102.79(14) y
C21 C20 C17 177.4(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.388(3) y
C1 C10 1.394(3) y
C2 C3 1.381(2) y
C3 O3 1.377(2) y
C3 C4 1.380(3) y
C4 C5 1.396(2) y
C5 C10 1.399(2) y
C5 C6 1.517(2) y
C6 C7 1.521(2) y
C7 C8 1.526(2) y
C8 C14 1.516(2) y
C8 C9 1.538(2) y
C9 C10 1.523(2) y
C9 C11 1.536(2) y
C11 C12 1.536(2) y
C12 C13 1.531(2) y
C13 C18 1.536(2) y
C13 C14 1.539(2) y
C13 C17 1.564(2) y
C14 C15 1.521(2) y
C15 C16 1.540(3) y
C16 C17 1.560(3) y
C17 O17 1.430(2) y
C17 C20 1.481(3) y
C20 C21 1.185(3) y
C25 O26 1.418(2) y
