#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/30/4503073.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_4503073
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         '2(C20 H24 O2), H2 O'
_chemical_formula_sum            'C20 H25 O2.5'
_chemical_formula_weight         305.40
_chemical_name_common            'ethinyl estradiol hemi-hydrate'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 91.099(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.0163(7)
_cell_length_b                   6.5877(5)
_cell_length_c                   12.0946(5)
_cell_measurement_reflns_used    64
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      27.500
_cell_measurement_theta_min      2.540
_cell_volume                     1674.18(16)
_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
;
DIRDIF (Beurskens et al., 1996),
;
_diffrn_ambient_temperature      208(2)
_diffrn_detector_area_resol_mean 18.4
_diffrn_measured_fraction_theta_full 0.499
_diffrn_measured_fraction_theta_max 0.500
_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  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17653
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.54
_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  0.9899
_exptl_absorpt_correction_T_min  0.8226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS multiscan (Sheldrick, 1996)'
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rather long rod'
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_Flack   1.1(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.060
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3853
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0509
_refine_ls_R_factor_obs          0.0509
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[σ²(Fo²)+(0.0359P)²+0.6951P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0954
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_obs         0.0881
_refine_ls_wR_factor_ref         0.0954
_reflns_number_gt                3018
_reflns_number_observed          3018
_reflns_number_total             3853
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0702277-file005.cif
_cod_data_source_block           eehemi
_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 (25
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      'C 2'
_cod_original_formula_sum        'C20 H25 O2.50'
_cod_database_code               4503073
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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 0.08416(10) -0.3151(3) 0.64055(17) 0.0259(5) Uani 1 d .
H1 H 0.0682(9) -0.419(3) 0.5845(17) 0.028(6) Uiso 1 d .
C2 C 0.07020(10) -0.3492(4) 0.75005(17) 0.0275(5) Uani 1 d .
H2 H 0.0498(9) -0.466(3) 0.7766(16) 0.021(5) Uiso 1 d .
C3 C 0.08781(10) -0.2055(3) 0.82846(16) 0.0277(5) Uani 1 d .
O3 O 0.07210(9) -0.2247(3) 0.93814(13) 0.0410(5) Uani 1 d .
H3 H 0.0524(12) -0.327(5) 0.948(2) 0.041(8) Uiso 1 d .
C4 C 0.12101(10) -0.0357(3) 0.79750(17) 0.0279(5) Uani 1 d .
H4 H 0.1337(10) 0.066(3) 0.8508(18) 0.031(6) Uiso 1 d .
C5 C 0.13536(9) -0.0018(3) 0.68684(16) 0.0225(4) Uani 1 d .
C6 C 0.17134(11) 0.1902(4) 0.65955(17) 0.0281(5) Uani 1 d .
H6A H 0.2066(10) 0.205(3) 0.7105(16) 0.022(5) Uiso 1 d .
H6B H 0.1428(10) 0.305(3) 0.6731(16) 0.026(6) Uiso 1 d .
C7 C 0.19432(10) 0.1985(4) 0.54121(16) 0.0241(5) Uani 1 d .
H7A H 0.2329(9) 0.117(3) 0.5338(16) 0.025(6) Uiso 1 d .
H7B H 0.2059(10) 0.339(4) 0.5214(17) 0.028(6) Uiso 1 d .
C8 C 0.14313(9) 0.1209(3) 0.46134(16) 0.0206(4) Uani 1 d .
H8 H 0.1022(8) 0.197(3) 0.4751(14) 0.011(5) Uiso 1 d .
C9 C 0.12957(9) -0.1041(3) 0.48400(16) 0.0202(4) Uani 1 d .
H9 H 0.1674(9) -0.179(3) 0.4709(15) 0.018(5) Uiso 1 d .
C10 C 0.11575(8) -0.1406(3) 0.60568(15) 0.0203(4) Uani 1 d .
C11 C 0.07786(10) -0.1873(4) 0.40437(16) 0.0272(5) Uani 1 d .
H11A H 0.0719(10) -0.330(4) 0.4166(17) 0.032(6) Uiso 1 d .
H11B H 0.0360(10) -0.119(4) 0.4220(17) 0.026(5) Uiso 1 d .
C12 C 0.09306(11) -0.1491(4) 0.28228(17) 0.0266(5) Uani 1 d .
H12A H 0.1313(10) -0.230(3) 0.2633(17) 0.027(6) Uiso 1 d .
H12B H 0.0569(11) -0.198(4) 0.2371(18) 0.030(6) Uiso 1 d .
C13 C 0.10711(10) 0.0741(3) 0.26128(17) 0.0235(5) Uani 1 d .
C14 C 0.16094(9) 0.1420(3) 0.34030(15) 0.0216(4) Uani 1 d .
H14 H 0.1968(9) 0.049(3) 0.3293(15) 0.011(5) Uiso 1 d .
C15 C 0.18181(12) 0.3491(4) 0.29653(17) 0.0319(5) Uani 1 d .
H15A H 0.2279(11) 0.374(4) 0.3105(19) 0.043(7) Uiso 1 d .
H15B H 0.1579(11) 0.462(4) 0.334(2) 0.040(7) Uiso 1 d .
C16 C 0.16738(14) 0.3398(4) 0.16977(19) 0.0373(6) Uani 1 d .
H16A H 0.2069(13) 0.357(4) 0.127(2) 0.061(9) Uiso 1 d .
H16B H 0.1358(13) 0.445(5) 0.151(2) 0.058(8) Uiso 1 d .
C17 C 0.13721(10) 0.1282(4) 0.14793(17) 0.0288(5) Uani 1 d .
O17 O 0.09179(8) 0.1452(3) 0.05842(13) 0.0368(4) Uani 1 d .
H17 H 0.0854(13) 0.039(5) 0.031(2) 0.055(10) Uiso 1 d .
C18 C 0.04661(11) 0.2021(4) 0.2734(2) 0.0340(6) Uani 1 d .
H18A H 0.0267(10) 0.179(4) 0.3397(18) 0.030(6) Uiso 1 d .
H18B H 0.0557(13) 0.354(5) 0.257(2) 0.068(9) Uiso 1 d .
H18C H 0.0148(10) 0.155(4) 0.2162(18) 0.033(6) Uiso 1 d .
C20 C 0.18636(11) -0.0192(4) 0.11653(17) 0.0330(5) Uani 1 d .
C21 C 0.22458(13) -0.1360(5) 0.0874(2) 0.0502(7) Uani 1 d .
H21 H 0.2572(14) -0.225(5) 0.064(2) 0.064(9) Uiso 1 d .
O30 O 0.0000 0.4371(4) 0.0000 0.0344(6) Uani 1 d S
H30 H 0.0262(12) 0.360(4) 0.028(2) 0.051(8) 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 122.3(2) y
C1 C2 C3 119.1(2) y
C4 C3 O3 117.98(19) y
C4 C3 C2 120.01(19) y
O3 C3 C2 122.0(2) y
C3 C4 C5 120.8(2) y
C4 C5 C10 120.19(19) y
C4 C5 C6 117.43(18) y
C10 C5 C6 122.37(17) y
C5 C6 C7 113.86(18) y
C6 C7 C8 110.63(17) y
C7 C8 C14 113.30(16) y
C7 C8 C9 110.05(16) y
C14 C8 C9 108.04(16) y
C10 C9 C8 111.35(16) y
C10 C9 C11 113.74(16) y
C8 C9 C11 111.31(17) y
C1 C10 C5 117.50(17) y
C1 C10 C9 121.45(17) y
C5 C10 C9 121.05(17) y
C12 C11 C9 112.69(17) y
C13 C12 C11 111.26(18) y
C12 C13 C14 108.73(17) y
C12 C13 C18 110.55(19) y
C14 C13 C18 112.49(18) y
C12 C13 C17 116.73(17) y
C14 C13 C17 100.03(15) y
C18 C13 C17 107.99(18) y
C8 C14 C15 119.40(18) y
C8 C14 C13 112.34(16) y
C15 C14 C13 104.92(16) y
C14 C15 C16 104.67(18) y
C17 C16 C15 105.91(18) y
O17 C17 C20 108.46(17) y
O17 C17 C16 108.8(2) y
C20 C17 C16 110.48(19) y
O17 C17 C13 113.92(17) y
C20 C17 C13 111.94(18) y
C16 C17 C13 103.09(16) 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 1.380(3) y
C1 C10 1.397(3) y
C2 C3 1.385(3) y
C3 C4 1.374(3) y
C3 O3 1.379(2) y
C4 C5 1.395(3) y
C5 C10 1.398(3) y
C5 C6 1.513(3) y
C6 C7 1.520(3) y
C7 C8 1.521(3) y
C8 C14 1.524(2) y
C8 C9 1.535(3) y
C9 C10 1.525(3) y
C9 C11 1.539(3) y
C11 C12 1.537(3) y
C12 C13 1.522(3) y
C13 C14 1.533(3) y
C13 C18 1.535(3) y
C13 C17 1.562(3) y
C14 C15 1.531(3) y
C15 C16 1.558(3) y
C16 C17 1.552(3) y
C17 O17 1.434(3) y
C17 C20 1.473(3) y
C20 C21 1.171(3) y
