#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007076.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_2007076
loop_
_publ_author_name
'Lalancette, R. A.'
'Thompson, H. W.'
'Brunskill, A. P. J.'
_publ_section_title
;
 (+)-3-Oxo-23,24-dinor-5\a-cholan-22-oic Acid: Hydrogen-Bonding
 Patterns in a Steroidal Keto Acid and its Monohydrate
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              421
_journal_page_last               424
_journal_volume                  54
_journal_year                    1998
_chemical_formula_analytical     'C22 H34 O3'
_chemical_formula_moiety         'C22 H34 O3'
_chemical_formula_structural     'C22 H34 O3'
_chemical_formula_sum            'C22 H34 O3'
_chemical_formula_weight         346.49
_chemical_melting_point          526
_chemical_name_common
;
22,23-Bisnor-5\a-cholanic acid-3-one
;
_chemical_name_systematic
;
(+)-22,23-Bisnor-3-oxo-5\a-cholanic Acid
;
_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'
_audit_creation_method           SHELXTL/PC
_cell_angle_alpha                90.00
_cell_angle_beta                 93.380(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.433(2)
_cell_length_b                   6.6290(10)
_cell_length_c                   24.559(4)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.20
_cell_measurement_theta_min      3.24
_cell_volume                     2020.6(6)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Fait, 1991)'
_computing_data_reduction        XSCANS
_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       '2\q/\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.121
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            4058
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        1.4
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   'Face-indexed numerical'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_meas      1.140(10)
_exptl_crystal_density_method    'flotation in hexane/CCl~4~'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.121
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_method     SHELXL93
_refine_ls_goodness_of_fit_all   1.05
_refine_ls_goodness_of_fit_obs   1.22
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3568
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.12
_refine_ls_restrained_S_obs      1.22
_refine_ls_R_factor_all          0.188
_refine_ls_R_factor_obs          0.073
_refine_ls_shift/esd_max         0.00
_refine_ls_shift/esd_mean        0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0309P)^2^+0.5593P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.156
_refine_ls_wR_factor_obs         0.109
_reflns_number_observed          1590
_reflns_number_total             3575
_reflns_observed_criterion       >4sigma(F)
_[local]_cod_data_source_file    fg1381.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  C2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '526K' was changed to '526' - 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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2007076
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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.152(4) 0.086(3) 0.044(2) -0.002(3) -0.004(2) 0.004(3)
O2 0.199(4) 0.055(2) 0.066(2) -0.010(3) 0.069(3) -0.004(2)
O3 0.253(6) 0.055(3) 0.074(3) 0.001(4) 0.072(3) 0.007(3)
C1 0.073(4) 0.082(5) 0.042(3) 0.006(3) 0.010(3) 0.006(3)
C2 0.083(5) 0.099(5) 0.049(3) -0.001(4) 0.013(3) 0.009(3)
C3 0.118(6) 0.057(4) 0.051(4) -0.008(4) -0.009(4) 0.006(3)
C4 0.078(5) 0.084(5) 0.063(4) -0.021(4) -0.015(4) 0.000(4)
C5 0.076(5) 0.059(4) 0.047(3) -0.016(3) -0.010(3) -0.001(3)
C6 0.060(4) 0.117(6) 0.070(4) -0.020(4) -0.014(3) 0.009(4)
C7 0.069(5) 0.123(6) 0.066(4) -0.028(4) 0.003(3) 0.007(4)
C8 0.053(4) 0.072(4) 0.054(3) -0.012(3) 0.002(3) 0.001(3)
C9 0.057(4) 0.053(4) 0.040(3) -0.012(3) 0.000(3) -0.004(2)
C10 0.045(4) 0.059(4) 0.042(3) 0.000(3) 0.003(3) -0.007(3)
C11 0.053(4) 0.097(4) 0.045(3) -0.006(3) 0.003(3) 0.014(3)
C12 0.071(4) 0.078(4) 0.046(3) 0.001(3) 0.007(3) 0.014(3)
C13 0.065(4) 0.055(3) 0.036(3) -0.014(3) 0.010(3) -0.005(3)
C14 0.066(4) 0.066(4) 0.050(3) -0.024(3) 0.009(3) -0.001(3)
C15 0.078(5) 0.135(6) 0.066(4) -0.034(5) 0.009(4) 0.018(4)
C16 0.091(5) 0.117(6) 0.077(4) -0.039(5) 0.012(4) 0.027(4)
C17 0.093(5) 0.048(3) 0.044(3) -0.028(3) 0.008(3) -0.005(3)
C18 0.114(5) 0.055(4) 0.053(3) -0.022(4) 0.011(3) -0.002(3)
C19 0.084(5) 0.057(4) 0.051(3) -0.022(3) -0.005(3) -0.003(3)
C20 0.096(5) 0.057(4) 0.048(3) -0.017(4) 0.009(3) -0.005(3)
C21 0.125(7) 0.151(7) 0.052(4) -0.019(6) -0.005(4) 0.026(4)
C22 0.126(6) 0.052(4) 0.042(3) -0.022(4) 0.016(3) -0.010(3)
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_type_symbol
O1 0.2417(4) 0.6178(6) -0.02824(15) 0.0943(14) Uani d . 1 O
O2 0.2549(4) 0.1306(6) 0.4972(2) 0.104(2) Uani d . 1 O
O3 0.3257(4) -0.0853(7) 0.4442(2) 0.125(2) Uani d . 1 O
H3 0.2989(15) -0.181(5) 0.4725(15) 0.080 Uiso calc R 1 H
C1 0.3655(4) 0.5407(8) 0.1068(2) 0.065(2) Uani d . 1 C
C2 0.3575(4) 0.6472(10) 0.0512(2) 0.077(2) Uani d . 1 C
C3 0.2495(6) 0.6302(9) 0.0215(2) 0.076(2) Uani d . 1 C
C4 0.1532(4) 0.6427(10) 0.0546(2) 0.076(2) Uani d . 1 C
C5 0.1660(4) 0.5286(8) 0.1092(2) 0.061(2) Uani d . 1 C
C6 0.0665(4) 0.5512(10) 0.1411(2) 0.083(2) Uani d . 1 C
C7 0.0765(4) 0.4269(11) 0.1935(2) 0.086(2) Uani d . 1 C
C8 0.1785(4) 0.4735(9) 0.2283(2) 0.060(2) Uani d . 1 C
C9 0.2785(4) 0.4531(8) 0.1948(2) 0.0499(14) Uani d . 1 C
C10 0.2710(4) 0.5886(8) 0.1425(2) 0.0487(13) Uani d . 1 C
C11 0.3827(4) 0.4808(9) 0.2305(2) 0.065(2) Uani d . 1 C
C12 0.3887(4) 0.3498(9) 0.2825(2) 0.065(2) Uani d . 1 C
C13 0.2913(4) 0.3818(8) 0.3159(2) 0.0518(14) Uani d . 1 C
C14 0.1915(4) 0.3362(8) 0.2782(2) 0.060(2) Uani d . 1 C
C15 0.0998(4) 0.3267(11) 0.3168(2) 0.093(2) Uani d . 1 C
C16 0.1522(5) 0.2329(11) 0.3691(2) 0.095(2) Uani d . 1 C
C17 0.2745(5) 0.2253(8) 0.3625(2) 0.061(2) Uani d . 1 C
C18 0.2913(4) 0.5964(9) 0.3390(2) 0.074(2) Uani d . 1 C
C19 0.2710(4) 0.8132(8) 0.1579(2) 0.064(2) Uani d . 1 C
C20 0.3386(5) 0.2510(8) 0.4181(2) 0.067(2) Uani d . 1 C
C21 0.4600(6) 0.2389(11) 0.4140(2) 0.110(2) Uani d . 1 C
C22 0.3023(5) 0.0983(10) 0.4573(2) 0.073(2) Uani d . 1 C
H1A 0.4323 0.5803 0.1263 0.083 Uiso calc R 1 H
H1B 0.3683 0.3962 0.1009 0.083 Uiso calc R 1 H
H2A 0.3744 0.7889 0.0566 0.083(4) Uiso calc R 1 H
H2B 0.4113 0.5906 0.0286 0.083(4) Uiso calc R 1 H
H4A 0.0915 0.5883 0.0334 0.083(4) Uiso calc R 1 H
H4B 0.1384 0.7835 0.0619 0.083(4) Uiso calc R 1 H
H5A 0.1723 0.3851 0.1004 0.063(6) Uiso calc R 1 H
H6A 0.0038 0.5069 0.1189 0.083(4) Uiso calc R 1 H
H6B 0.0564 0.6922 0.1501 0.083(4) Uiso calc R 1 H
H7A 0.0145 0.4533 0.2146 0.083(4) Uiso calc R 1 H
H7B 0.0758 0.2847 0.1842 0.083(4) Uiso calc R 1 H
H8A 0.1743 0.6133 0.2410 0.063(6) Uiso calc R 1 H
H9A 0.2790 0.3132 0.1819 0.063(6) Uiso calc R 1 H
H11A 0.3893 0.6215 0.2410 0.083(4) Uiso calc R 1 H
H11B 0.4435 0.4481 0.2091 0.083(4) Uiso calc R 1 H
H12A 0.3929 0.2087 0.2723 0.083(4) Uiso calc R 1 H
H12B 0.4536 0.3832 0.3045 0.083(4) Uiso calc R 1 H
H14A 0.2007 0.1990 0.2644 0.063(6) Uiso calc R 1 H
H15A 0.0413 0.2431 0.3018 0.083(4) Uiso calc R 1 H
H15B 0.0722 0.4605 0.3239 0.083(4) Uiso calc R 1 H
H16A 0.1244 0.0979 0.3742 0.083(4) Uiso calc R 1 H
H16B 0.1367 0.3140 0.4005 0.083(4) Uiso calc R 1 H
H17A 0.2915 0.0914 0.3484 0.063(6) Uiso calc R 1 H
H18A 0.2311(15) 0.6128(17) 0.3613(11) 0.107(12) Uiso calc R 1 H
H18B 0.286(3) 0.6916(9) 0.3095(2) 0.107(12) Uiso calc R 1 H
H18C 0.3570(12) 0.6194(18) 0.3606(11) 0.107(12) Uiso calc R 1 H
H19A 0.2142(15) 0.8391(11) 0.1817(10) 0.096(12) Uiso calc R 1 H
H19B 0.260(2) 0.8931(8) 0.1254(2) 0.096(12) Uiso calc R 1 H
H19C 0.3390(9) 0.8479(13) 0.1760(11) 0.096(12) Uiso calc R 1 H
H20A 0.3218(5) 0.3846(8) 0.4324(2) 0.063(6) Uiso calc R 1 H
H21A 0.4839(7) 0.352(3) 0.3936(14) 0.121(14) Uiso calc R 1 H
H21B 0.4779(6) 0.116(3) 0.3960(14) 0.121(14) Uiso calc R 1 H
H21C 0.4947(6) 0.241(6) 0.4500(2) 0.121(14) 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 0.0181 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
C22 O3 H3 109.5(3) ?
C2 C1 C10 113.6(4) ?
C3 C2 C1 114.1(5) ?
O1 C3 C4 122.1(6) ?
O1 C3 C2 120.6(6) ?
C4 C3 C2 117.2(5) ?
C3 C4 C5 113.8(5) ?
C6 C5 C4 111.0(5) ?
C6 C5 C10 113.0(4) ?
C4 C5 C10 112.0(4) ?
C5 C6 C7 110.8(5) ?
C8 C7 C6 112.8(5) ?
C7 C8 C14 112.0(4) ?
C7 C8 C9 110.9(4) ?
C14 C8 C9 109.0(4) ?
C11 C9 C8 111.6(4) ?
C11 C9 C10 114.1(4) ?
C8 C9 C10 112.2(4) ?
C19 C10 C1 110.5(4) ?
C19 C10 C5 111.4(4) ?
C1 C10 C5 107.1(4) ?
C19 C10 C9 110.9(4) ?
C1 C10 C9 109.8(4) ?
C5 C10 C9 107.0(4) ?
C9 C11 C12 113.8(4) ?
C13 C12 C11 111.6(4) ?
C12 C13 C18 110.3(4) ?
C12 C13 C14 106.8(4) ?
C18 C13 C14 112.8(5) ?
C12 C13 C17 116.6(5) ?
C18 C13 C17 110.0(4) ?
C14 C13 C17 99.9(4) ?
C15 C14 C8 118.4(5) ?
C15 C14 C13 103.9(4) ?
C8 C14 C13 114.2(4) ?
C14 C15 C16 103.9(5) ?
C15 C16 C17 107.4(4) ?
C16 C17 C20 111.4(4) ?
C16 C17 C13 103.3(5) ?
C20 C17 C13 119.1(4) ?
C22 C20 C21 110.3(5) ?
C22 C20 C17 109.7(4) ?
C21 C20 C17 113.4(4) ?
O2 C22 O3 120.1(6) ?
O2 C22 C20 126.5(6) y
O3 C22 C20 113.4(5) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 1.222(5) y
O2 C22 1.192(6) y
O3 C22 1.297(7) y
O3 H3 1.01(5) y
C1 C2 1.534(6) ?
C1 C10 1.541(6) ?
C2 C3 1.495(7) ?
C3 C4 1.488(7) ?
C4 C5 1.540(6) ?
C5 C6 1.510(7) ?
C5 C10 1.551(6) ?
C6 C7 1.527(7) ?
C7 C8 1.519(6) ?
C8 C14 1.529(6) ?
C8 C9 1.537(6) ?
C9 C11 1.532(6) ?
C9 C10 1.566(6) ?
C10 C19 1.536(7) ?
C11 C12 1.542(6) ?
C12 C13 1.518(6) ?
C13 C18 1.531(7) ?
C13 C14 1.535(6) ?
C13 C17 1.567(7) ?
C14 C15 1.526(6) ?
C15 C16 1.536(7) ?
C16 C17 1.539(7) ?
C17 C20 1.549(6) ?
C20 C22 1.485(7) ?
C20 C21 1.520(8) ?
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 -47.6(7) ?
C1 C2 C3 O1 -145.4(5) ?
C1 C2 C3 C4 38.5(8) ?
O1 C3 C4 C5 143.3(5) ?
C2 C3 C4 C5 -40.7(8) ?
C3 C4 C5 C6 178.8(5) ?
C3 C4 C5 C10 51.5(7) ?
C4 C5 C6 C7 176.3(5) ?
C10 C5 C6 C7 -56.9(6) ?
C5 C6 C7 C8 53.8(7) ?
C6 C7 C8 C14 -175.5(5) ?
C6 C7 C8 C9 -53.4(7) ?
C7 C8 C9 C11 -174.8(5) ?
C14 C8 C9 C11 -51.0(6) ?
C7 C8 C9 C10 55.8(6) ?
C14 C8 C9 C10 179.6(4) ?
C2 C1 C10 C19 -64.5(6) ?
C2 C1 C10 C5 57.0(6) ?
C2 C1 C10 C9 172.9(5) ?
C6 C5 C10 C19 -63.8(5) ?
C4 C5 C10 C19 62.4(6) ?
C6 C5 C10 C1 175.2(5) ?
C4 C5 C10 C1 -58.6(6) ?
C6 C5 C10 C9 57.5(6) ?
C4 C5 C10 C9 -176.3(5) ?
C11 C9 C10 C19 -62.8(5) ?
C8 C9 C10 C19 65.2(5) ?
C11 C9 C10 C1 59.6(5) ?
C8 C9 C10 C1 -172.4(4) ?
C11 C9 C10 C5 175.4(4) ?
C8 C9 C10 C5 -56.5(5) ?
C8 C9 C11 C12 50.6(6) ?
C10 C9 C11 C12 178.9(4) ?
C9 C11 C12 C13 -54.2(6) ?
C11 C12 C13 C18 -66.6(5) ?
C11 C12 C13 C14 56.4(6) ?
C11 C12 C13 C17 167.0(4) ?
C7 C8 C14 C15 -55.0(7) ?
C9 C8 C14 C15 -178.2(5) ?
C7 C8 C14 C13 -178.0(5) ?
C9 C8 C14 C13 58.9(5) ?
C12 C13 C14 C15 168.3(5) ?
C18 C13 C14 C15 -70.3(5) ?
C17 C13 C14 C15 46.5(5) ?
C12 C13 C14 C8 -61.2(6) ?
C18 C13 C14 C8 60.1(6) ?
C17 C13 C14 C8 176.9(4) ?
C8 C14 C15 C16 -163.1(5) ?
C13 C14 C15 C16 -35.1(6) ?
C14 C15 C16 C17 9.4(7) ?
C15 C16 C17 C20 148.0(5) ?
C15 C16 C17 C13 19.0(6) ?
C12 C13 C17 C16 -154.1(5) ?
C18 C13 C17 C16 79.3(5) ?
C14 C13 C17 C16 -39.5(5) ?
C12 C13 C17 C20 81.9(6) ?
C18 C13 C17 C20 -44.7(6) ?
C14 C13 C17 C20 -163.6(5) ?
C16 C17 C20 C22 54.6(6) ?
C13 C17 C20 C22 174.6(5) ?
C16 C17 C20 C21 178.4(6) y
C13 C17 C20 C21 -61.5(7) ?
C21 C20 C22 O2 121.8(7) ?
C17 C20 C22 O2 -112.6(7) y
C21 C20 C22 O3 -59.1(7) ?
C17 C20 C22 O3 66.5(7) ?
H20A C20 C22 O2 4.4(7) y