#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/28/2012807.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_2012807
loop_
_publ_author_name
'Newman, Jacob M.'
'Lalancette, Roger A.'
'Thompson, Hugh W.'
_publ_section_title
;
 (+)-3,11-Dioxoandrost-4-ene-17β-carboxylic acid: catemeric hydrogen
 bonding in a steroidal keto acid
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o402
_journal_page_last               o404
_journal_paper_doi               10.1107/S0108270102009393
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C20 H26 O4'
_chemical_formula_moiety         'C20 H26 O4'
_chemical_formula_sum            'C20 H26 O4'
_chemical_formula_weight         330.41
_chemical_melting_point          543
_chemical_name_systematic
;
 (+)-3,11-Dioxoandrost-4-ene-17β-carboxylic acid
;
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.98(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.699(2)
_cell_length_b                   11.409(3)
_cell_length_c                   11.764(3)
_cell_measurement_reflns_used    36
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      11.3
_cell_measurement_theta_min      3.5
_cell_volume                     895.7(4)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       2θ/θ
_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  0.057
_diffrn_reflns_av_sigmaI/netI    0.063
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3582
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        'variation <3.5'
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.11
_refine_diff_density_min         -0.11
_refine_ls_extinction_coef       0.0187(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         1658
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0103P)²+0.0570P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.077
_refine_ls_wR_factor_ref         0.085
_reflns_number_gt                1245
_reflns_number_total             1657
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1378.cif
_cod_data_source_block           I
_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 (2 times).

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

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 (2
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 (2 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               2012807
_cod_database_fobs_code          2012807
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.5654(5) 0.4336(3) 1.0660(3) 0.1145(12) Uani d . 1 . . O
O2 -0.0837(4) 0.4693(2) 0.6111(2) 0.0634(7) Uani d . 1 . . O
O3 -0.0381(5) 0.6385(3) 0.1058(2) 0.0923(9) Uani d . 1 . . O
O4 -0.0811(6) 0.4650(3) 0.1819(3) 0.0926(9) Uani d . 1 . . O
C1 0.2202(6) 0.4289(3) 0.8147(3) 0.0610(10) Uani d . 1 . . C
C2 0.2677(7) 0.4239(4) 0.9436(3) 0.0769(12) Uani d . 1 . . C
C3 0.4718(7) 0.4692(4) 0.9789(3) 0.0731(11) Uani d . 1 . . C
C4 0.5462(6) 0.5626(3) 0.9109(3) 0.0637(9) Uani d . 1 . . C
C5 0.4484(5) 0.6036(3) 0.8153(3) 0.0508(9) Uani d . 1 . . C
C6 0.5225(5) 0.7108(3) 0.7567(3) 0.0592(9) Uani d . 1 . . C
C7 0.5276(5) 0.6919(3) 0.6284(3) 0.0581(10) Uani d . 1 . . C
C8 0.3268(4) 0.6520(3) 0.5721(3) 0.0438(7) Uani d . 1 . . C
C9 0.2582(4) 0.5393(2) 0.6326(3) 0.0432(7) Uani d . 1 . . C
C10 0.2503(5) 0.5523(3) 0.7644(3) 0.0460(8) Uani d . 1 . . C
C11 0.0711(5) 0.4878(3) 0.5674(3) 0.0475(8) Uani d . 1 . . C
C12 0.0858(5) 0.4657(3) 0.4422(3) 0.0541(9) Uani d . 1 . . C
C13 0.1393(5) 0.5809(3) 0.3855(3) 0.0460(8) Uani d . 1 . . C
C14 0.3369(4) 0.6266(3) 0.4454(3) 0.0478(8) Uani d . 1 . . C
C15 0.3973(5) 0.7249(3) 0.3673(3) 0.0591(10) Uani d . 1 . . C
C16 0.3272(6) 0.6814(4) 0.2462(3) 0.0748(11) Uani d . 1 . . C
C17 0.1947(5) 0.5736(3) 0.2598(3) 0.0611(10) Uani d . 1 . . C
C18 -0.0349(5) 0.6666(3) 0.3925(3) 0.0515(8) Uani d . 1 . . C
C19 0.0792(5) 0.6361(4) 0.7939(3) 0.0639(10) Uani d . 1 . . C
C20 0.0140(6) 0.5647(4) 0.1736(3) 0.0666(10) Uani d . 1 . . C
H4 -0.212(8) 0.458(5) 0.133(4) 0.126(18) Uiso d . 1 . . H
H1A 0.0823 0.4048 0.7962 0.073 Uiso calc R 1 . . H
H1B 0.3056 0.3737 0.7791 0.073 Uiso calc R 1 . . H
H2A 0.1696 0.4700 0.9801 0.092 Uiso calc R 1 . . H
H2B 0.2576 0.3434 0.9692 0.092 Uiso calc R 1 . . H
H4A 0.6692 0.5960 0.9351 0.076 Uiso calc R 1 . . H
H6A 0.6562 0.7300 0.7898 0.071 Uiso calc R 1 . . H
H6B 0.4356 0.7765 0.7697 0.071 Uiso calc R 1 . . H
H7A 0.5657 0.7646 0.5934 0.070 Uiso calc R 1 . . H
H7B 0.6284 0.6336 0.6154 0.070 Uiso calc R 1 . . H
H8 0.2279 0.7140 0.5804 0.053 Uiso calc R 1 . . H
H9 0.3642 0.4817 0.6236 0.052 Uiso calc R 1 . . H
H12A -0.0411 0.4365 0.4074 0.065 Uiso calc R 1 . . H
H12B 0.1880 0.4074 0.4321 0.065 Uiso calc R 1 . . H
H14 0.4357 0.5639 0.4404 0.057 Uiso calc R 1 . . H
H15A 0.5412 0.7370 0.3754 0.071 Uiso calc R 1 . . H
H15B 0.3313 0.7978 0.3841 0.071 Uiso calc R 1 . . H
H16A 0.2518 0.7423 0.2039 0.090 Uiso calc R 1 . . H
H16B 0.4417 0.6608 0.2052 0.090 Uiso calc R 1 . . H
H17 0.2772 0.5035 0.2524 0.073 Uiso calc R 1 . . H
H18A -0.0695 0.6711 0.4699 0.077 Uiso calc R 1 . . H
H18B -0.1486 0.6396 0.3443 0.077 Uiso calc R 1 . . H
H18C 0.0041 0.7428 0.3677 0.077 Uiso calc R 1 . . H
H19A 0.0786 0.6420 0.8753 0.096 Uiso calc R 1 . . H
H19B -0.0472 0.6056 0.7622 0.096 Uiso calc R 1 . . H
H19C 0.1005 0.7122 0.7625 0.096 Uiso calc R 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 0.0016 '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 113.1(3) ?
C3 C2 C1 111.9(3) ?
O1 C3 C4 122.1(4) ?
O1 C3 C2 120.7(4) ?
C4 C3 C2 117.0(4) ?
C5 C4 C3 123.8(3) ?
C4 C5 C6 120.8(3) ?
C4 C5 C10 122.9(3) ?
C6 C5 C10 116.2(3) ?
C5 C6 C7 112.0(3) ?
C8 C7 C6 112.3(3) ?
C7 C8 C14 111.8(2) ?
C7 C8 C9 109.6(3) ?
C14 C8 C9 109.2(3) ?
C11 C9 C8 110.5(3) ?
C11 C9 C10 115.9(3) ?
C8 C9 C10 114.3(2) ?
C5 C10 C1 109.7(3) ?
C5 C10 C19 108.0(3) ?
C1 C10 C19 110.5(3) ?
C5 C10 C9 108.9(2) ?
C1 C10 C9 108.1(3) ?
C19 C10 C9 111.7(3) ?
O2 C11 C12 121.0(3) ?
O2 C11 C9 123.2(3) ?
C12 C11 C9 115.7(3) ?
C11 C12 C13 108.7(3) ?
C12 C13 C18 108.4(3) ?
C12 C13 C14 108.5(3) ?
C18 C13 C14 112.9(3) ?
C12 C13 C17 116.9(3) ?
C18 C13 C17 109.3(3) ?
C14 C13 C17 100.8(2) ?
C8 C14 C15 119.0(3) ?
C8 C14 C13 113.8(2) ?
C15 C14 C13 103.6(3) ?
C14 C15 C16 104.1(3) ?
C17 C16 C15 107.1(3) ?
C20 C17 C16 114.9(3) ?
C20 C17 C13 113.4(3) ?
C16 C17 C13 104.1(3) ?
O3 C20 O4 123.2(4) ?
O3 C20 C17 124.8(4) y
O4 C20 C17 112.0(3) y
C20 O4 H4 115(3) ?
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 H2A 109.2 ?
C1 C2 H2A 109.2 ?
C3 C2 H2B 109.2 ?
C1 C2 H2B 109.2 ?
H2A C2 H2B 107.9 ?
C5 C4 H4A 118.1 ?
C3 C4 H4A 118.1 ?
C5 C6 H6A 109.2 ?
C7 C6 H6A 109.2 ?
C5 C6 H6B 109.2 ?
C7 C6 H6B 109.2 ?
H6A C6 H6B 107.9 ?
C8 C7 H7A 109.2 ?
C6 C7 H7A 109.2 ?
C8 C7 H7B 109.2 ?
C6 C7 H7B 109.2 ?
H7A C7 H7B 107.9 ?
C7 C8 H8 108.7 ?
C14 C8 H8 108.7 ?
C9 C8 H8 108.7 ?
C11 C9 H9 105.0 ?
C8 C9 H9 105.0 ?
C10 C9 H9 105.0 ?
C11 C12 H12A 110.0 ?
C13 C12 H12A 110.0 ?
C11 C12 H12B 110.0 ?
C13 C12 H12B 110.0 ?
H12A C12 H12B 108.3 ?
C8 C14 H14 106.5 ?
C15 C14 H14 106.5 ?
C13 C14 H14 106.5 ?
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 ?
C17 C16 H16A 110.3 ?
C15 C16 H16A 110.3 ?
C17 C16 H16B 110.3 ?
C15 C16 H16B 110.3 ?
H16A C16 H16B 108.5 ?
C20 C17 H17 108.0 ?
C16 C17 H17 108.0 ?
C13 C17 H17 108.0 ?
C13 C18 H18A 109.5 ?
C13 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C13 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C10 C19 H19A 109.5 ?
C10 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C10 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 . 1.223(5) ?
O2 C11 . 1.215(4) ?
O3 C20 . 1.192(4) y
O4 C20 . 1.311(5) y
C1 C2 . 1.524(5) ?
C1 C10 . 1.547(5) ?
C2 C3 . 1.487(6) ?
C3 C4 . 1.447(5) ?
C4 C5 . 1.336(5) ?
C5 C6 . 1.509(5) ?
C5 C10 . 1.525(4) ?
C6 C7 . 1.528(5) ?
C7 C8 . 1.517(4) ?
C8 C14 . 1.526(4) ?
C8 C9 . 1.557(4) ?
C9 C11 . 1.528(4) ?
C9 C10 . 1.563(4) ?
C10 C19 . 1.555(5) ?
C11 C12 . 1.507(4) ?
C12 C13 . 1.530(4) ?
C13 C18 . 1.530(4) ?
C13 C14 . 1.536(5) ?
C13 C17 . 1.558(4) ?
C14 C15 . 1.527(4) ?
C15 C16 . 1.542(5) ?
C16 C17 . 1.533(5) ?
C17 C20 . 1.514(5) ?
O4 H4 . 1.01(6) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C4 H4A . 0.9300 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8 . 0.9800 ?
C9 H9 . 0.9800 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C14 H14 . 0.9800 ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17 . 0.9800 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
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
C10 C1 C2 C3 -53.9(5)
C1 C2 C3 O1 -151.9(4)
C1 C2 C3 C4 32.8(5)
O1 C3 C4 C5 179.9(4)
C2 C3 C4 C5 -4.8(6)
C3 C4 C5 C6 172.4(3)
C3 C4 C5 C10 -2.8(6)
C4 C5 C6 C7 132.6(4)
C10 C5 C6 C7 -51.8(4)
C5 C6 C7 C8 54.3(4)
C6 C7 C8 C14 -176.7(3)
C6 C7 C8 C9 -55.5(4)
C7 C8 C9 C11 -172.2(3)
C14 C8 C9 C11 -49.5(3)
C7 C8 C9 C10 54.9(3)
C14 C8 C9 C10 177.6(3)
C4 C5 C10 C1 -17.8(4)
C6 C5 C10 C1 166.8(3)
C4 C5 C10 C19 102.7(4)
C6 C5 C10 C19 -72.7(3)
C4 C5 C10 C9 -135.8(3)
C6 C5 C10 C9 48.8(4)
C2 C1 C10 C5 45.4(4)
C2 C1 C10 C19 -73.6(4)
C2 C1 C10 C9 163.9(3)
C11 C9 C10 C5 179.5(3)
C8 C9 C10 C5 -50.2(3)
C11 C9 C10 C1 60.5(4)
C8 C9 C10 C1 -169.3(3)
C11 C9 C10 C19 -61.3(3)
C8 C9 C10 C19 69.0(3)
C8 C9 C11 O2 -124.3(3)
C10 C9 C11 O2 7.8(4)
C8 C9 C11 C12 53.0(3)
C10 C9 C11 C12 -174.9(3)
O2 C11 C12 C13 120.3(3)
C9 C11 C12 C13 -57.1(4)
C11 C12 C13 C18 -65.3(4)
C11 C12 C13 C14 57.7(3)
C11 C12 C13 C17 170.7(3)
C7 C8 C14 C15 -59.7(4)
C9 C8 C14 C15 178.9(3)
C7 C8 C14 C13 177.6(3)
C9 C8 C14 C13 56.2(3)
C12 C13 C14 C8 -60.8(3)
C18 C13 C14 C8 59.4(3)
C17 C13 C14 C8 175.8(3)
C12 C13 C14 C15 168.4(3)
C18 C13 C14 C15 -71.4(3)
C17 C13 C14 C15 45.1(3)
C8 C14 C15 C16 -162.6(3)
C13 C14 C15 C16 -35.0(3)
C14 C15 C16 C17 10.9(4)
C15 C16 C17 C20 141.5(3)
C15 C16 C17 C13 16.8(4)
C12 C13 C17 C20 79.4(4)
C18 C13 C17 C20 -44.2(4)
C14 C13 C17 C20 -163.3(3)
C12 C13 C17 C16 -155.0(3)
C18 C13 C17 C16 81.4(3)
C14 C13 C17 C16 -37.7(3)
C16 C17 C20 O3 -6.9(5)
C13 C17 C20 O3 112.7(4)
C16 C17 C20 O4 173.3(3)
C13 C17 C20 O4 -67.1(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 18642641
