#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/54/2015455.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_2015455
loop_
_publ_author_name
'Kikolski, Elizabeth M.'
'Thompson, Hugh W.'
'Lalancette, Roger A.'
_publ_section_title
;
 (+)-3,11-Dioxo-5α-androstanecarboxylic acid: catemeric hydrogen
 bonding in a steroidal diketo acid
;
_journal_coeditor_code           SK3023
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o397
_journal_page_last               o398
_journal_paper_doi               10.1107/S0108270106017677
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C20 H28 O4'
_chemical_formula_moiety         'C20 H28 O4'
_chemical_formula_sum            'C20 H28 O4'
_chemical_formula_weight         332.42
_chemical_melting_point          559
_chemical_name_systematic
;
 (+)-3,11-Dioxo-5α-androstanecarboxylic acid
;
_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                   6.36840(10)
_cell_length_b                   11.61020(10)
_cell_length_c                   22.7430(2)
_cell_measurement_reflns_used    8793
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.95
_cell_measurement_theta_min      3.89
_cell_volume                     1681.58(3)
_computing_cell_refinement       'SMART WNT/2000'
_computing_data_collection       'SMART WNT/2000 (Bruker, 2000)'
_computing_data_reduction        'SAINT-Plus (Bruker,2000)'
_computing_molecular_graphics    'SHELXTL (Bruker,2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART CCD Apex-II area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_av_sigmaI/netI    0.026
_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       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8793
_diffrn_reflns_theta_full        64.95
_diffrn_reflns_theta_max         64.95
_diffrn_reflns_theta_min         3.89
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Blessing, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.17
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.040
_refine_ls_R_factor_gt           0.035
_refine_ls_shift/su_max          0.00
_refine_ls_shift/su_mean         0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0422P)²+0.4552P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.082
_refine_ls_wR_factor_ref         0.085
_reflns_number_gt                2503
_reflns_number_total             2741
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3023.cif
_cod_data_source_block           I
_cod_database_code               2015455
_cod_database_fobs_code          2015455
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_type_symbol
_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
O O1 1.1200(2) 0.61313(11) 0.19770(6) 0.0309(3) Uani d . 1
O O2 0.4872(2) 0.16426(11) 0.19024(6) 0.0300(3) Uani d . 1
O O3 0.5549(2) -0.35589(12) 0.09136(6) 0.0367(4) Uani d . 1
O O4 0.4724(2) -0.25845(12) 0.17271(6) 0.0351(4) Uani d . 1
C C1 0.8089(3) 0.35923(16) 0.20835(8) 0.0251(4) Uani d . 1
C C2 0.8218(3) 0.49173(17) 0.20910(9) 0.0271(5) Uani d . 1
C C3 1.0114(3) 0.53648(16) 0.17732(9) 0.0268(4) Uani d . 1
C C4 1.0544(3) 0.48312(17) 0.11828(9) 0.0299(5) Uani d . 1
C C5 1.0369(3) 0.35187(16) 0.12008(8) 0.0252(4) Uani d . 1
C C6 1.0876(3) 0.29936(17) 0.06036(8) 0.0267(5) Uani d . 1
C C7 1.1005(3) 0.16881(17) 0.06601(9) 0.0259(4) Uani d . 1
C C8 0.8982(3) 0.11726(16) 0.09008(8) 0.0219(4) Uani d . 1
C C9 0.8390(3) 0.17514(16) 0.14962(8) 0.0224(4) Uani d . 1
C C10 0.8251(3) 0.30905(16) 0.14571(8) 0.0234(4) Uani d . 1
C C11 0.6477(3) 0.11519(16) 0.17612(8) 0.0225(4) Uani d . 1
C C12 0.6658(3) -0.01498(16) 0.18246(8) 0.0258(5) Uani d . 1
C C13 0.7120(3) -0.06801(16) 0.12211(8) 0.0226(4) Uani d . 1
C C14 0.9142(3) -0.01284(17) 0.09808(8) 0.0235(4) Uani d . 1
C C15 0.9660(3) -0.08786(16) 0.04466(9) 0.0271(5) Uani d . 1
C C16 0.9092(3) -0.21043(17) 0.06534(9) 0.0303(5) Uani d . 1
C C17 0.7743(3) -0.19684(16) 0.12155(9) 0.0264(5) Uani d . 1
C C18 0.5233(3) -0.05009(16) 0.08124(9) 0.0270(4) Uani d . 1
C C19 0.6374(3) 0.34631(17) 0.10812(9) 0.0275(5) Uani d . 1
C C20 0.5912(3) -0.27927(16) 0.12537(8) 0.0268(5) Uani d . 1
H H1A 0.6740 0.3349 0.2261 0.030 Uiso calc R 1
H H1B 0.9238 0.3274 0.2327 0.030 Uiso calc R 1
H H2A 0.6939 0.5238 0.1906 0.032 Uiso calc R 1
H H2B 0.8259 0.5186 0.2504 0.032 Uiso calc R 1
H H4 0.3755 -0.3074 0.1745 0.053 Uiso calc R 1
H H4A 1.1974 0.5049 0.1053 0.036 Uiso calc R 1
H H4B 0.9532 0.5138 0.0892 0.036 Uiso calc R 1
H H5 1.1487 0.3245 0.1476 0.030 Uiso calc R 1
H H6A 1.2231 0.3300 0.0458 0.032 Uiso calc R 1
H H6B 0.9770 0.3203 0.0317 0.032 Uiso calc R 1
H H7A 1.1302 0.1350 0.0269 0.031 Uiso calc R 1
H H7B 1.2183 0.1485 0.0925 0.031 Uiso calc R 1
H H8 0.7832 0.1333 0.0613 0.026 Uiso calc R 1
H H9 0.9582 0.1584 0.1769 0.027 Uiso calc R 1
H H12A 0.5330 -0.0468 0.1983 0.031 Uiso calc R 1
H H12B 0.7803 -0.0342 0.2102 0.031 Uiso calc R 1
H H14 1.0267 -0.0269 0.1279 0.028 Uiso calc R 1
H H15A 1.1167 -0.0823 0.0344 0.033 Uiso calc R 1
H H15B 0.8808 -0.0651 0.0101 0.033 Uiso calc R 1
H H16A 1.0382 -0.2549 0.0741 0.036 Uiso calc R 1
H H16B 0.8291 -0.2514 0.0345 0.036 Uiso calc R 1
H H17 0.8672 -0.2112 0.1562 0.032 Uiso calc R 1
H H18A 0.3966 -0.0813 0.0998 0.040 Uiso calc R 1
H H18B 0.5484 -0.0899 0.0439 0.040 Uiso calc R 1
H H18C 0.5042 0.0324 0.0739 0.040 Uiso calc R 1
H H19A 0.6502 0.4283 0.0985 0.041 Uiso calc R 1
H H19B 0.5071 0.3333 0.1300 0.041 Uiso calc R 1
H H19C 0.6349 0.3011 0.0717 0.041 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C20 O4 H4 109.5 ?
C7 C8 C14 112.07(16) ?
C7 C8 C9 110.35(15) ?
C14 C8 C9 109.87(15) ?
C7 C8 H8 108.1 ?
C14 C8 H8 108.1 ?
C9 C8 H8 108.1 ?
O2 C11 C12 120.33(17) ?
O2 C11 C9 124.22(17) ?
C12 C11 C9 115.42(16) ?
O1 C3 C2 121.75(18) ?
O1 C3 C4 122.49(19) ?
C2 C3 C4 115.73(17) ?
C11 C12 C13 109.17(15) ?
C11 C12 H12A 109.8 ?
C13 C12 H12A 109.8 ?
C11 C12 H12B 109.8 ?
C13 C12 H12B 109.8 ?
H12A C12 H12B 108.3 ?
C6 C5 C4 111.08(15) ?
C6 C5 C10 113.01(15) ?
C4 C5 C10 113.14(16) ?
C6 C5 H5 106.3 ?
C4 C5 H5 106.3 ?
C10 C5 H5 106.3 ?
C3 C4 C5 111.93(16) ?
C3 C4 H4A 109.2 ?
C5 C4 H4A 109.2 ?
C3 C4 H4B 109.2 ?
C5 C4 H4B 109.2 ?
H4A C4 H4B 107.9 ?
C11 C9 C8 109.85(15) ?
C11 C9 C10 115.57(16) ?
C8 C9 C10 113.22(15) ?
C11 C9 H9 105.8 ?
C8 C9 H9 105.8 ?
C10 C9 H9 105.8 ?
C8 C14 C15 118.91(16) ?
C8 C14 C13 113.51(16) ?
C15 C14 C13 103.02(16) ?
C8 C14 H14 106.9 ?
C15 C14 H14 106.9 ?
C13 C14 H14 106.9 ?
C2 C1 C10 112.55(15) ?
C2 C1 H1A 109.1 ?
C10 C1 H1A 109.1 ?
C2 C1 H1B 109.1 ?
C10 C1 H1B 109.1 ?
H1A C1 H1B 107.8 ?
C5 C6 C7 109.54(16) ?
C5 C6 H6A 109.8 ?
C7 C6 H6A 109.8 ?
C5 C6 H6B 109.8 ?
C7 C6 H6B 109.8 ?
H6A C6 H6B 108.2 ?
C12 C13 C18 109.75(16) ?
C12 C13 C14 108.15(16) ?
C18 C13 C14 112.58(15) ?
C12 C13 C17 116.41(16) ?
C18 C13 C17 109.10(15) ?
C14 C13 C17 100.64(16) ?
O3 C20 O4 122.88(19) ?
O3 C20 C17 125.50(19) y
O4 C20 C17 111.61(16) y
C19 C10 C1 110.89(16) ?
C19 C10 C5 112.23(15) ?
C1 C10 C5 106.51(15) ?
C19 C10 C9 110.94(16) ?
C1 C10 C9 109.12(15) ?
C5 C10 C9 106.95(16) ?
C15 C16 C17 106.73(15) ?
C15 C16 H16A 110.4 ?
C17 C16 H16A 110.4 ?
C15 C16 H16B 110.4 ?
C17 C16 H16B 110.4 ?
H16A C16 H16B 108.6 ?
C20 C17 C13 114.44(17) ?
C20 C17 C16 114.28(16) ?
C13 C17 C16 104.34(16) ?
C20 C17 H17 107.8 ?
C13 C17 H17 107.8 ?
C16 C17 H17 107.8 ?
C8 C7 C6 112.06(16) ?
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 ?
C3 C2 C1 112.57(16) ?
C3 C2 H2A 109.1 ?
C1 C2 H2A 109.1 ?
C3 C2 H2B 109.1 ?
C1 C2 H2B 109.1 ?
H2A C2 H2B 107.8 ?
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 ?
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 ?
C14 C15 C16 103.45(16) ?
C14 C15 H15A 111.1 ?
C16 C15 H15A 111.1 ?
C14 C15 H15B 111.1 ?
C16 C15 H15B 111.1 ?
H15A C15 H15B 109.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C11 1.213(2) ?
O3 C20 1.201(2) y
O4 C20 1.338(2) y
O4 H4 0.84 ?
O1 C3 1.219(2) ?
C8 C7 1.523(3) ?
C8 C14 1.525(2) ?
C8 C9 1.558(3) ?
C8 H8 1.0000 ?
C11 C12 1.523(2) ?
C11 C9 1.527(3) ?
C3 C2 1.500(3) ?
C3 C4 1.504(3) ?
C12 C13 1.533(2) ?
C12 H12A 0.9900 ?
C12 H12B 0.9900 ?
C5 C6 1.523(3) ?
C5 C4 1.528(3) ?
C5 C10 1.551(3) ?
C5 H5 1.0000 ?
C4 H4A 0.99 ?
C4 H4B 0.99 ?
C9 C10 1.560(2) ?
C9 H9 1.0000 ?
C14 C15 1.531(3) ?
C14 C13 1.539(3) ?
C14 H14 1.00 ?
C1 C2 1.541(2) ?
C1 C10 1.543(3) ?
C1 H1A 0.99 ?
C1 H1B 0.99 ?
C6 C7 1.523(3) ?
C6 H6A 0.99 ?
C6 H6B 0.9900 ?
C13 C18 1.533(3) ?
C13 C17 1.548(3) ?
C20 C17 1.511(3) ?
C10 C19 1.532(3) ?
C16 C15 1.542(3) ?
C16 C17 1.548(3) ?
C16 H16A 0.9900 ?
C16 H16B 0.9900 ?
C17 H17 1.0000 ?
C7 H7A 0.9900 ?
C7 H7B 0.9900 ?
C2 H2A 0.9900 ?
C2 H2B 0.9900 ?
C19 H19A 0.9800 ?
C19 H19B 0.9800 ?
C19 H19C 0.9800 ?
C18 H18A 0.9800 ?
C18 H18B 0.9800 ?
C18 H18C 0.9800 ?
C15 H15A 0.9900 ?
C15 H15B 0.9900 ?
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
O4 H4 O1 1_445 0.84 1.94 2.7537(18) 162 yes
C19 H19A O3 1_565 0.98 2.58 3.518(2) 159 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
O2 C11 C12 C13 121.12(19)
C9 C11 C12 C13 -57.0(2)
O1 C3 C4 C5 135.6(2)
C2 C3 C4 C5 -46.1(2)
C6 C5 C4 C3 -178.26(17)
C10 C5 C4 C3 53.4(2)
O2 C11 C9 C8 -124.94(19)
C12 C11 C9 C8 53.1(2)
O2 C11 C9 C10 4.6(3)
C12 C11 C9 C10 -177.30(16)
C7 C8 C9 C11 -174.74(15)
C14 C8 C9 C11 -50.7(2)
C7 C8 C9 C10 54.4(2)
C14 C8 C9 C10 178.48(16)
C7 C8 C14 C15 -58.4(2)
C9 C8 C14 C15 178.58(16)
C7 C8 C14 C13 -179.75(15)
C9 C8 C14 C13 57.2(2)
C4 C5 C6 C7 171.63(16)
C10 C5 C6 C7 -60.0(2)
C11 C12 C13 C18 -65.9(2)
C11 C12 C13 C14 57.2(2)
C11 C12 C13 C17 169.56(17)
C8 C14 C13 C12 -60.6(2)
C15 C14 C13 C12 169.52(15)
C8 C14 C13 C18 60.9(2)
C15 C14 C13 C18 -69.05(19)
C8 C14 C13 C17 176.89(15)
C15 C14 C13 C17 46.97(18)
C2 C1 C10 C19 -64.6(2)
C2 C1 C10 C5 57.8(2)
C2 C1 C10 C9 172.95(16)
C6 C5 C10 C19 -64.5(2)
C4 C5 C10 C19 62.9(2)
C6 C5 C10 C1 174.01(16)
C4 C5 C10 C1 -58.7(2)
C6 C5 C10 C9 57.4(2)
C4 C5 C10 C9 -175.25(16)
C11 C9 C10 C19 -59.5(2)
C8 C9 C10 C19 68.4(2)
C11 C9 C10 C1 63.0(2)
C8 C9 C10 C1 -169.09(16)
C11 C9 C10 C5 177.82(15)
C8 C9 C10 C5 -54.2(2)
O3 C20 C17 C13 125.6(2)
O4 C20 C17 C13 -55.6(2)
O3 C20 C17 C16 5.3(3)
O4 C20 C17 C16 -175.78(16)
C12 C13 C17 C20 80.9(2)
C18 C13 C17 C20 -44.0(2)
C14 C13 C17 C20 -162.55(16)
C12 C13 C17 C16 -153.51(17)
C18 C13 C17 C16 81.65(19)
C14 C13 C17 C16 -36.94(19)
C15 C16 C17 C20 139.58(17)
C15 C16 C17 C13 13.9(2)
C14 C8 C7 C6 -177.68(16)
C9 C8 C7 C6 -54.9(2)
C5 C6 C7 C8 57.6(2)
O1 C3 C2 C1 -135.7(2)
C4 C3 C2 C1 46.0(2)
C10 C1 C2 C3 -52.8(2)
C8 C14 C15 C16 -165.08(17)
C13 C14 C15 C16 -38.54(19)
C17 C16 C15 C14 15.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21180857
