#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/63/2006300.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_2006300
loop_
_publ_author_name
'Brunskill, Andrew P. J.'
'Lalancette, Roger A.'
'Thompson, Hugh W.'
_publ_section_title
;
 (+)-3-Oxoandrost-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              903
_journal_page_last               906
_journal_paper_doi               10.1107/S0108270197002515
_journal_volume                  53
_journal_year                    1997
_chemical_formula_analytical     'C20 H28 O3'
_chemical_formula_moiety         'C20 H28 O3'
_chemical_formula_structural     'C20 H28 O3'
_chemical_formula_sum            'C20 H28 O3'
_chemical_formula_weight         316.44
_chemical_melting_point          527
_chemical_name_common
;
(+)-4-Androsten-3-one-17β-carboxylic Acid
;
_chemical_name_systematic
;
(+)-3-Oxoandrost-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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 102.060(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.9880(10)
_cell_length_b                   11.2540(10)
_cell_length_c                   11.480(2)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.2
_cell_measurement_theta_min      5.4
_cell_volume                     882.9(2)
_computing_cell_refinement       'XSCANS (Siemens, 1991)'
_computing_data_collection       'XSCANS (Fait, 1991)'
_computing_data_reduction        'XSCANS (Siemens, 1991)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  SHELXTL/PC
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2θ/θ scans'
_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  0.035
_diffrn_reflns_av_sigmaI/netI    0.068
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4621
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        0.35
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   'Face-indexed numerical'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_meas      1.1910(10)
_exptl_crystal_density_method    'flotation in cyclohexane/CCl~4~'
_exptl_crystal_description       'triangular prism'
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.14
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   1.4(17)
_refine_ls_extinction_coef       0.0000(10)
_refine_ls_extinction_method     'SHELXTL/PC (Sheldrick, 1994)'
_refine_ls_goodness_of_fit_all   1.02
_refine_ls_goodness_of_fit_obs   1.08
_refine_ls_hydrogen_treatment    'H atoms: see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3870
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.03
_refine_ls_restrained_S_obs      1.08
_refine_ls_R_factor_all          0.088
_refine_ls_R_factor_obs          .053
_refine_ls_shift/esd_max         0.00
_refine_ls_shift/esd_mean        0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0514P)²+0.0823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.130
_refine_ls_wR_factor_obs         .113
_reflns_number_observed          2727
_reflns_number_total             3886
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            fg1258.cif
_cod_data_source_block           andoid
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_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 (4 times).

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

The following automatic conversions were performed:

'_chemical_melting_point' value '527K' was changed to '527' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '527K' was changed to '527' - the
value should be numeric and without a unit
designator.

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

'_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 (4
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 (7
times).

'_geom_torsion_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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.0823P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.0823P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2006300
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 -.0578(3) 1.3491(2) .6122(2) .0655(6) Uani d . 1 . O
O2 .6414(4) .3838(2) .8409(2) .0879(8) Uani d . 1 . O
O3 .6183(4) .4524(2) .6579(2) .0785(7) Uani d . 1 . O
H3 .728(6) .415(4) .661(3) .089(13) Uiso d . 1 . H
C1 .2305(4) 1.0874(2) .5843(2) .0465(6) Uani d . 1 . C
C2 .1948(4) 1.2208(2) .5811(3) .0541(7) Uani d . 1 . C
C3 .0280(4) 1.2548(2) .6370(2) .0499(7) Uani d . 1 . C
C4 -.0195(4) 1.1746(2) .7262(2) .0498(7) Uani d . 1 . C
C5 .0814(3) 1.0751(2) .7637(2) .0412(6) Uani d . 1 . C
C6 .0379(4) 1.0058(3) .8660(2) .0510(7) Uani d . 1 . C
C7 .0338(4) .8727(2) .8465(2) .0479(6) Uani d . 1 . C
C8 .2228(3) .8313(2) .8132(2) .0363(5) Uani d . 1 . C
C9 .2500(3) .8949(2) .6988(2) .0348(5) Uani d . 1 . C
C10 .2516(3) 1.0335(2) .7091(2) .0355(5) Uani d . 1 . C
C11 .4274(4) .8469(2) .6531(2) .0490(7) Uani d . 1 . C
C12 .4323(4) .7116(2) .6440(2) .0491(7) Uani d . 1 . C
C13 .4156(4) .6532(2) .7614(2) .0394(6) Uani d . 1 . C
C14 .2258(3) .6975(2) .7932(2) .0382(6) Uani d . 1 . C
C15 .1965(4) .6147(2) .8942(3) .0507(7) Uani d . 1 . C
C16 .2777(5) .4934(3) .8632(3) .0581(7) Uani d . 1 . C
C17 .3779(4) .5167(2) .7580(2) .0465(6) Uani d . 1 . C
C18 .5964(4) .6801(2) .8592(2) .0488(6) Uani d . 1 . C
C19 .4419(4) 1.0781(3) .7921(3) .0573(7) Uani d . 1 . C
C20 .5590(4) .4436(2) .7597(3) .0535(7) Uani d . 1 . C
H1A .3486 1.0711 .5553 .052(5) Uiso calc R 1 . H
H1B .1225 1.0488 .5309 .052(5) Uiso calc R 1 . H
H2A .3124 1.2608 .6226 .061(6) Uiso calc R 1 . H
H2B .1678 1.2476 .4989 .061(6) Uiso calc R 1 . H
H4A -.1262 1.1933 .7595 .057(8) Uiso calc R 1 . H
H6A -.0881 1.0308 .8803 .061(6) Uiso calc R 1 . H
H6B .1360 1.0242 .9368 .061(6) Uiso calc R 1 . H
H7A -.0765 .8520 .7833 .049(5) Uiso calc R 1 . H
H7B .0176 .8327 .9186 .049(5) Uiso calc R 1 . H
H8B .3327 .8522 .8780 .038(6) Uiso calc R 1 . H
H9A .1345 .8749 .6375 .029(6) Uiso calc R 1 . H
H11A .4257 .8805 .5750 .049(5) Uiso calc R 1 . H
H11B .5464 .8735 .7062 .049(5) Uiso calc R 1 . H
H12A .3250 .6851 .5815 .059(6) Uiso calc R 1 . H
H12B .5538 .6873 .6229 .059(6) Uiso calc R 1 . H
H14A .1202 .6800 .7246 .033(6) Uiso calc R 1 . H
H15A .0590 .6084 .8967 .059(6) Uiso calc R 1 . H
H15B .2681 .6433 .9706 .059(6) Uiso calc R 1 . H
H16A .3711 .4625 .9310 .065(6) Uiso calc R 1 . H
H16B .1724 .4363 .8410 .065(6) Uiso calc R 1 . H
H17A .2836 .4984 .6842 .049(7) Uiso calc R 1 . H
H18A .5826 .6425 .9320 .059(5) Uiso calc R 1 . H
H18B .6085 .7644 .8711 .059(5) Uiso calc R 1 . H
H18C .7112 .6502 .8356 .059(5) Uiso calc R 1 . H
H19A .5527 1.0537 .7607 .083(6) Uiso calc R 1 . H
H19B .4392 1.1633 .7967 .083(6) Uiso calc R 1 . H
H19C .4517 1.0451 .8702 .083(6) 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 113.3(2) ?
C3 C2 C1 112.4(2) ?
O1 C3 C4 122.0(3) y
O1 C3 C2 120.7(3) y
C4 C3 C2 117.2(2) ?
C5 C4 C3 124.1(2) ?
C4 C5 C6 120.5(2) ?
C4 C5 C10 121.6(2) ?
C6 C5 C10 117.8(2) ?
C5 C6 C7 113.7(2) ?
C6 C7 C8 110.5(2) ?
C7 C8 C14 112.4(2) ?
C7 C8 C9 109.8(2) ?
C14 C8 C9 108.8(2) ?
C11 C9 C8 112.3(2) ?
C11 C9 C10 112.4(2) ?
C8 C9 C10 113.5(2) ?
C5 C10 C1 109.3(2) ?
C5 C10 C19 106.9(2) ?
C1 C10 C19 110.4(2) ?
C5 C10 C9 110.0(2) ?
C1 C10 C9 109.0(2) ?
C19 C10 C9 111.2(2) ?
C12 C11 C9 113.8(2) ?
C13 C12 C11 111.3(2) ?
C12 C13 C14 107.5(2) ?
C12 C13 C18 111.0(2) ?
C14 C13 C18 112.5(2) ?
C12 C13 C17 116.5(2) ?
C14 C13 C17 100.2(2) ?
C18 C13 C17 108.8(2) ?
C8 C14 C13 113.4(2) ?
C8 C14 C15 118.6(2) ?
C13 C14 C15 104.0(2) ?
C14 C15 C16 104.4(2) ?
C17 C16 C15 106.2(2) y
C20 C17 C16 114.5(2) ?
C20 C17 C13 113.7(2) ?
C16 C17 C13 104.5(2) y
O2 C20 O3 122.9(3) y
O2 C20 C17 125.8(3) y
O3 C20 C17 111.4(2) y
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(3) y
O2 C20 . 1.195(3) y
O3 C20 . 1.322(4) y
O3 H3 . .87(4) y
C1 C2 . 1.522(4) ?
C1 C10 . 1.534(3) ?
C2 C3 . 1.493(4) ?
C3 C4 . 1.454(4) ?
C4 C5 . 1.345(4) ?
C5 C6 . 1.493(4) ?
C5 C10 . 1.529(3) ?
C6 C7 . 1.514(4) ?
C7 C8 . 1.522(3) ?
C8 C14 . 1.523(3) ?
C8 C9 . 1.542(3) ?
C9 C11 . 1.542(3) ?
C9 C10 . 1.565(3) ?
C10 C19 . 1.548(4) ?
C11 C12 . 1.527(4) ?
C12 C13 . 1.525(3) ?
C13 C14 . 1.530(3) ?
C13 C18 . 1.535(4) ?
C13 C17 . 1.558(3) ?
C14 C15 . 1.534(3) ?
C15 C16 . 1.547(4) ?
C16 C17 . 1.541(4) ?
C17 C20 . 1.506(4) ?
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 -52.3(3) ?
C1 C2 C3 O1 -158.1(3) ?
C1 C2 C3 C4 25.3(4) ?
O1 C3 C4 C5 -174.1(3) ?
C2 C3 C4 C5 2.4(4) ?
C3 C4 C5 C6 172.5(3) ?
C3 C4 C5 C10 -3.5(4) ?
C4 C5 C6 C7 137.3(3) ?
C10 C5 C6 C7 -46.4(3) ?
C5 C6 C7 C8 53.7(3) ?
C6 C7 C8 C14 179.7(2) ?
C6 C7 C8 C9 -59.0(3) ?
C7 C8 C9 C11 -173.9(2) ?
C14 C8 C9 C11 -50.5(3) ?
C7 C8 C9 C10 57.3(3) ?
C14 C8 C9 C10 -179.4(2) ?
C4 C5 C10 C1 -22.5(3) ?
C6 C5 C10 C1 161.3(2) ?
C4 C5 C10 C19 97.0(3) ?
C6 C5 C10 C19 -79.1(3) ?
C4 C5 C10 C9 -142.1(2) ?
C6 C5 C10 C9 41.7(3) ?
C2 C1 C10 C5 49.7(3) ?
C2 C1 C10 C19 -67.6(3) ?
C2 C1 C10 C9 170.0(2) ?
C11 C9 C10 C5 -175.7(2) ?
C8 C9 C10 C5 -46.9(3) ?
C11 C9 C10 C1 64.5(3) ?
C8 C9 C10 C1 -166.8(2) ?
C11 C9 C10 C19 -57.5(3) ?
C8 C9 C10 C19 71.3(3) ?
C8 C9 C11 C12 49.6(3) ?
C10 C9 C11 C12 179.0(2) ?
C9 C11 C12 C13 -53.1(3) ?
C11 C12 C13 C14 57.1(3) ?
C11 C12 C13 C18 -66.3(3) ?
C11 C12 C13 C17 168.5(2) ?
C7 C8 C14 C13 -179.2(2) ?
C9 C8 C14 C13 59.0(3) ?
C7 C8 C14 C15 -56.8(3) ?
C9 C8 C14 C15 -178.6(2) ?
C12 C13 C14 C8 -62.4(3) ?
C18 C13 C14 C8 60.1(3) ?
C17 C13 C14 C8 175.5(2) ?
C12 C13 C14 C15 167.5(2) ?
C18 C13 C14 C15 -70.1(2) ?
C17 C13 C14 C15 45.3(3) ?
C8 C14 C15 C16 -161.0(2) ?
C13 C14 C15 C16 -33.9(3) ?
C14 C15 C16 C17 8.5(3) ?
C15 C16 C17 C20 144.4(3) ?
C15 C16 C17 C13 19.4(3) ?
C12 C13 C17 C20 79.4(3) ?
C14 C13 C17 C20 -165.1(2) ?
C18 C13 C17 C20 -46.9(3) ?
C12 C13 C17 C16 -155.1(2) ?
C14 C13 C17 C16 -39.6(3) ?
C18 C13 C17 C16 78.6(2) ?
C16 C17 C20 O2 -10.3(4) y
C13 C17 C20 O2 109.6(3) ?
C16 C17 C20 O3 169.2(2) ?
C13 C17 C20 O3 -70.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 89868
2 PubChem 99472
