#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/67/2206765.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2206765
loop_
_publ_author_name
'Chun-Nian Xia'
'Wei-Xiao Hu'
'Wei Zhou'
_publ_section_title
;
 17a-Methyl-4-androstene-3b,17b-diol monohydrate
;
_journal_coeditor_code           OB6554
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2896
_journal_page_last               o2898
_journal_paper_doi               10.1107/S1600536805025316
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C20 H32 O2, H2 O'
_chemical_formula_moiety         'C20 H32 O2, H2 O'
_chemical_formula_sum            'C20 H34 O3'
_chemical_formula_weight         322.47
_chemical_name_systematic
;
17a-Methyl-4-androstene-3b,17b-diol monohydrate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   6.812(3)
_cell_length_b                   12.082(5)
_cell_length_c                   22.802(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.54
_cell_measurement_theta_min      10.66
_cell_volume                     1876.7(12)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD (McArdle, 2000)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0127
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2283
_diffrn_reflns_theta_full        25.18
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        0.3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_correction_T_min  0.9438
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.149
_refine_ls_abs_structure_details 'see text'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         1957
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0526P)²+0.2016P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                1440
_reflns_number_total             1957
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6554.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2206765
_cod_database_fobs_code          2206765
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 -0.1678(3) 0.38788(17) 0.47013(7) 0.0628(5) Uani d . 1 O
H1 -0.0731 0.4184 0.4853 0.094 Uiso calc R 1 H
O2 0.3430(3) 0.51674(16) 0.01352(8) 0.0650(5) Uani d . 1 O
H2 0.2463 0.5548 0.0063 0.097 Uiso calc R 1 H
C1 -0.1414(4) 0.5229(2) 0.32148(10) 0.0565(6) Uani d . 1 C
H1A -0.1739 0.5967 0.3077 0.068 Uiso calc R 1 H
H1B -0.2237 0.4707 0.3005 0.068 Uiso calc R 1 H
C2 -0.1869(4) 0.5152(2) 0.38703(10) 0.0613(7) Uani d . 1 C
H2A -0.1020 0.5650 0.4087 0.074 Uiso calc R 1 H
H2B -0.3220 0.5367 0.3941 0.074 Uiso calc R 1 H
C3 -0.1546(4) 0.3980(2) 0.40745(10) 0.0535(6) Uani d . 1 C
H3 -0.2573 0.3516 0.3901 0.064 Uiso calc R 1 H
C4 0.0379(4) 0.3568(2) 0.38632(10) 0.0511(6) Uani d . 1 C
H4 0.0886 0.2944 0.4048 0.061 Uiso calc R 1 H
C5 0.1442(3) 0.4005(2) 0.34364(10) 0.0465(5) Uani d . 1 C
C6 0.3428(4) 0.3547(2) 0.32845(11) 0.0636(7) Uani d . 1 C
H6A 0.3671 0.2888 0.3516 0.076 Uiso calc R 1 H
H6B 0.4427 0.4088 0.3383 0.076 Uiso calc R 1 H
C7 0.3581(4) 0.3262(2) 0.26381(10) 0.0629(7) Uani d . 1 C
H7A 0.2712 0.2648 0.2551 0.075 Uiso calc R 1 H
H7B 0.4913 0.3032 0.2550 0.075 Uiso calc R 1 H
C8 0.3038(3) 0.42489(19) 0.22520(10) 0.0454(5) Uani d . 1 C
H8 0.3987 0.4843 0.2324 0.054 Uiso calc R 1 H
C9 0.0976(3) 0.46771(18) 0.24107(9) 0.0430(5) Uani d . 1 C
H9 0.0087 0.4051 0.2346 0.052 Uiso calc R 1 H
C10 0.0754(3) 0.49862(18) 0.30722(9) 0.0448(5) Uani d . 1 C
C11 0.0276(4) 0.5593(2) 0.19903(10) 0.0623(7) Uani d . 1 C
H11A -0.1093 0.5754 0.2071 0.075 Uiso calc R 1 H
H11B 0.1024 0.6261 0.2066 0.075 Uiso calc R 1 H
C12 0.0492(4) 0.5283(2) 0.13410(10) 0.0590(7) Uani d . 1 C
H12A -0.0409 0.4686 0.1249 0.071 Uiso calc R 1 H
H12B 0.0144 0.5916 0.1100 0.071 Uiso calc R 1 H
C13 0.2590(3) 0.49212(19) 0.11953(10) 0.0453(5) Uani d . 1 C
C14 0.3096(4) 0.39551(19) 0.16065(10) 0.0493(6) Uani d . 1 C
H14 0.2085 0.3390 0.1545 0.059 Uiso calc R 1 H
C15 0.4996(5) 0.3490(3) 0.13504(12) 0.0797(9) Uani d . 1 C
H15A 0.5131 0.2709 0.1441 0.096 Uiso calc R 1 H
H15B 0.6127 0.3883 0.1503 0.096 Uiso calc R 1 H
C16 0.4792(6) 0.3669(3) 0.06866(12) 0.0923(11) Uani d . 1 C
H16A 0.4649 0.2963 0.0488 0.111 Uiso calc R 1 H
H16B 0.5950 0.4037 0.0534 0.111 Uiso calc R 1 H
C17 0.2958(4) 0.4391(2) 0.05840(11) 0.0586(7) Uani d . 1 C
C18 0.2000(5) 0.6008(2) 0.32320(12) 0.0704(8) Uani d . 1 C
H18A 0.3350 0.5870 0.3135 0.106 Uiso calc R 1 H
H18B 0.1888 0.6153 0.3645 0.106 Uiso calc R 1 H
H18C 0.1539 0.6638 0.3016 0.106 Uiso calc R 1 H
C19 0.3999(4) 0.5890(2) 0.12704(12) 0.0663(7) Uani d . 1 C
H19A 0.3952 0.6147 0.1669 0.099 Uiso calc R 1 H
H19B 0.3625 0.6480 0.1011 0.099 Uiso calc R 1 H
H19C 0.5310 0.5655 0.1179 0.099 Uiso calc R 1 H
C20 0.1217(6) 0.3711(3) 0.03575(14) 0.0995(13) Uani d . 1 C
H20A 0.0134 0.4196 0.0276 0.149 Uiso calc R 1 H
H20B 0.0835 0.3181 0.0649 0.149 Uiso calc R 1 H
H20C 0.1590 0.3331 0.0005 0.149 Uiso calc R 1 H
O3 0.5588(3) 0.8328(2) 0.01034(11) 0.0746(6) Uani d D 1 O
H3X 0.585(7) 0.7671(15) 0.002(2) 0.139(17) Uiso d D 1 H
H3Y 0.441(2) 0.850(3) 0.0071(16) 0.115(14) Uiso d D 1 H
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 0.0000 '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 0.0000 '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
C3 O1 H1 109.5 ?
C17 O2 H2 109.5 ?
C2 C1 C10 112.88(19) ?
C2 C1 H1A 109.0 ?
C10 C1 H1A 109.0 ?
C2 C1 H1B 109.0 ?
C10 C1 H1B 109.0 ?
H1A C1 H1B 107.8 ?
C3 C2 C1 109.3(2) ?
C3 C2 H2A 109.8 ?
C1 C2 H2A 109.8 ?
C3 C2 H2B 109.8 ?
C1 C2 H2B 109.8 ?
H2A C2 H2B 108.3 ?
O1 C3 C4 110.5(2) no
O1 C3 C2 112.2(2) no
C4 C3 C2 110.1(2) ?
O1 C3 H3 108.0 ?
C4 C3 H3 108.0 ?
C2 C3 H3 108.0 ?
C5 C4 C3 126.1(2) ?
C5 C4 H4 117.0 ?
C3 C4 H4 117.0 ?
C4 C5 C6 121.1(2) ?
C4 C5 C10 122.9(2) ?
C6 C5 C10 116.0(2) ?
C5 C6 C7 111.7(2) ?
C5 C6 H6A 109.3 ?
C7 C6 H6A 109.3 ?
C5 C6 H6B 109.3 ?
C7 C6 H6B 109.3 ?
H6A C6 H6B 107.9 ?
C6 C7 C8 111.5(2) ?
C6 C7 H7A 109.3 ?
C8 C7 H7A 109.3 ?
C6 C7 H7B 109.3 ?
C8 C7 H7B 109.3 ?
H7A C7 H7B 108.0 ?
C14 C8 C7 111.8(2) ?
C14 C8 C9 109.33(18) ?
C7 C8 C9 110.36(19) ?
C14 C8 H8 108.4 ?
C7 C8 H8 108.4 ?
C9 C8 H8 108.4 ?
C8 C9 C11 112.2(2) ?
C8 C9 C10 113.34(18) ?
C11 C9 C10 113.53(18) ?
C8 C9 H9 105.6 ?
C11 C9 H9 105.6 ?
C10 C9 H9 105.6 ?
C5 C10 C1 109.19(19) ?
C5 C10 C18 108.97(19) no
C1 C10 C18 109.0(2) no
C5 C10 C9 108.11(18) ?
C1 C10 C9 110.04(18) ?
C18 C10 C9 111.49(19) ?
C12 C11 C9 113.3(2) ?
C12 C11 H11A 108.9 ?
C9 C11 H11A 108.9 ?
C12 C11 H11B 108.9 ?
C9 C11 H11B 108.9 ?
H11A C11 H11B 107.7 ?
C13 C12 C11 111.6(2) ?
C13 C12 H12A 109.3 ?
C11 C12 H12A 109.3 ?
C13 C12 H12B 109.3 ?
C11 C12 H12B 109.3 ?
H12A C12 H12B 108.0 ?
C19 C13 C12 110.1(2) no
C19 C13 C14 111.96(19) no
C12 C13 C14 107.10(19) ?
C19 C13 C17 108.4(2) ?
C12 C13 C17 117.6(2) ?
C14 C13 C17 101.41(18) ?
C8 C14 C15 118.7(2) ?
C8 C14 C13 114.15(19) ?
C15 C14 C13 103.7(2) ?
C8 C14 H14 106.5 ?
C15 C14 H14 106.5 ?
C13 C14 H14 106.5 ?
C14 C15 C16 104.4(2) ?
C14 C15 H15A 110.9 ?
C16 C15 H15A 110.9 ?
C14 C15 H15B 110.9 ?
C16 C15 H15B 110.9 ?
H15A C15 H15B 108.9 ?
C15 C16 C17 107.6(2) ?
C15 C16 H16A 110.2 ?
C17 C16 H16A 110.2 ?
C15 C16 H16B 110.2 ?
C17 C16 H16B 110.2 ?
H16A C16 H16B 108.5 ?
O2 C17 C20 106.6(2) no
O2 C17 C16 107.4(2) no
C20 C17 C16 112.1(3) ?
O2 C17 C13 114.1(2) no
C20 C17 C13 113.5(2) no
C16 C17 C13 103.2(2) ?
C10 C18 H18A 109.5 ?
C10 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C10 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C13 C19 H19A 109.5 ?
C13 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C13 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C17 C20 H20A 109.5 ?
C17 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C17 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
H3X O3 H3Y 115(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 1.437(3) yes
O1 H1 0.8200 no
O2 C17 1.425(3) yes
O2 H2 0.8200 no
C1 C2 1.529(3) ?
C1 C10 1.540(3) ?
C1 H1A 0.9700 ?
C1 H1B 0.9700 ?
C2 C3 1.506(4) ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 C4 1.483(4) yes
C3 H3 0.9800 ?
C4 C5 1.323(3) yes
C4 H4 0.9300 ?
C5 C6 1.502(3) ?
C5 C10 1.522(3) ?
C6 C7 1.517(3) ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 C8 1.528(3) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 C14 1.515(3) ?
C8 C9 1.540(3) ?
C8 H8 0.9800 ?
C9 C11 1.540(3) ?
C9 C10 1.561(3) ?
C9 H9 0.9800 ?
C10 C18 1.542(3) ?
C11 C12 1.534(3) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 C13 1.531(3) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 C19 1.524(3) ?
C13 C14 1.536(3) ?
C13 C17 1.554(3) ?
C14 C15 1.527(4) ?
C14 H14 0.9800 ?
C15 C16 1.535(4) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 C17 1.542(4) ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
C17 C20 1.532(4) ?
C18 H18A 0.9599 ?
C18 H18B 0.9599 ?
C18 H18C 0.9599 ?
C19 H19A 0.9599 ?
C19 H19B 0.9599 ?
C19 H19C 0.9599 ?
C20 H20A 0.9599 ?
C20 H20B 0.9599 ?
C20 H20C 0.9599 ?
O3 H3X 0.833(10) no
O3 H3Y 0.831(10) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O2 2_565 0.82 1.87 2.684(3) 174 yes
O2 H2 O3 4_465 0.82 1.90 2.711(3) 169 yes
O3 H3X O1 2_564 0.830(10) 2.090(13) 2.916(3) 171(5) yes
O3 H3Y O1 3 0.830(10) 1.987(17) 2.781(3) 160(4) yes
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_publ_flag
C10 C1 C2 C3 -63.9(3) ?
C1 C2 C3 O1 171.8(2) ?
C1 C2 C3 C4 48.3(3) ?
O1 C3 C4 C5 -141.7(2) ?
C2 C3 C4 C5 -17.1(3) yes
C3 C4 C5 C6 176.6(2) ?
C3 C4 C5 C10 -3.4(4) yes
C4 C5 C6 C7 126.3(3) ?
C10 C5 C6 C7 -53.7(3) ?
C5 C6 C7 C8 54.0(3) ?
C6 C7 C8 C14 -177.4(2) ?
C6 C7 C8 C9 -55.5(3) ?
C14 C8 C9 C11 -50.7(2) ?
C7 C8 C9 C11 -174.0(2) ?
C14 C8 C9 C10 179.09(18) ?
C7 C8 C9 C10 55.8(2) ?
C4 C5 C10 C1 -9.0(3) yes
C6 C5 C10 C1 171.0(2) ?
C4 C5 C10 C18 109.9(3) ?
C6 C5 C10 C18 -70.1(3) ?
C4 C5 C10 C9 -128.8(2) ?
C6 C5 C10 C9 51.3(3) ?
C2 C1 C10 C5 42.0(3) ?
C2 C1 C10 C18 -76.9(3) ?
C2 C1 C10 C9 160.5(2) ?
C8 C9 C10 C5 -52.0(2) ?
C11 C9 C10 C5 178.5(2) ?
C8 C9 C10 C1 -171.14(19) ?
C11 C9 C10 C1 59.3(3) ?
C8 C9 C10 C18 67.8(2) ?
C11 C9 C10 C18 -61.7(3) ?
C8 C9 C11 C12 50.1(3) ?
C10 C9 C11 C12 -179.8(2) ?
C9 C11 C12 C13 -53.7(3) ?
C11 C12 C13 C19 -65.5(3) ?
C11 C12 C13 C14 56.5(3) ?
C11 C12 C13 C17 169.7(2) ?
C7 C8 C14 C15 -56.5(3) ?
C9 C8 C14 C15 -178.9(2) ?
C7 C8 C14 C13 -179.2(2) ?
C9 C8 C14 C13 58.4(2) ?
C19 C13 C14 C8 59.8(3) ?
C12 C13 C14 C8 -61.0(3) ?
C17 C13 C14 C8 175.19(19) ?
C19 C13 C14 C15 -70.8(3) ?
C12 C13 C14 C15 168.4(2) ?
C17 C13 C14 C15 44.6(2) yes
C8 C14 C15 C16 -161.0(2) ?
C13 C14 C15 C16 -33.2(3) yes
C14 C15 C16 C17 8.8(3) yes
C15 C16 C17 O2 139.3(3) ?
C15 C16 C17 C20 -104.0(3) ?
C15 C16 C17 C13 18.5(3) yes
C19 C13 C17 O2 -36.5(3) ?
C12 C13 C17 O2 89.2(3) ?
C14 C13 C17 O2 -154.4(2) ?
C19 C13 C17 C20 -158.8(2) ?
C12 C13 C17 C20 -33.1(3) ?
C14 C13 C17 C20 83.2(3) ?
C19 C13 C17 C16 79.7(3) ?
C12 C13 C17 C16 -154.6(2) ?
C14 C13 C17 C16 -38.3(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21180351
