Enantiomeric Deoxycholic Acid: Total Synthesis, Characterization, and Preliminary Toxicity toward Colon Cancer Cell Lines
Bryson W. Katona; Nigam P. Rath; Shrikant Anant; William F. Stenson; Douglas F. Covey; Journal of Organic Chemistry 72 (2007) 9298–9307; doi:10.1021/jo701559q

data_4023040
_publ_section_title
;
 Enantiomeric Deoxycholic Acid: Total Synthesis, Characterization,
 and Preliminary Toxicity toward Colon Cancer Cell Lines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9298
_journal_page_last               9307
_journal_paper_doi               10.1021/jo701559q
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H38 O4'
_chemical_formula_weight         402.55
_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                 94.900(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7145(12)
_cell_length_b                   7.7115(9)
_cell_length_c                   14.613(2)
_cell_measurement_reflns_used    1901
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.49
_cell_measurement_theta_min      2.62
_cell_volume                     1090.7(2)
_computing_cell_refinement       'Bruker-Apex II'
_computing_data_collection       'Bruker-Apex II'
_computing_data_reduction        Bruker-SAINT
_computing_molecular_graphics    'Bruker-SHELXTL (Sheldrick, 2006)'
_computing_publication_material  'Bruker-SHELXTL (Sheldrick, 2006)'
_computing_structure_refinement  'Bruker-SHELXTL (Sheldrick, 2006)'
_computing_structure_solution    'Bruker-SHELXTL (Sheldrick, 2006)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0743
_diffrn_reflns_av_sigmaI/netI    0.0986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15546
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.40
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9777
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'sadabs v2.10'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(16)
_refine_ls_extinction_coef       0.0079(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3560
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1094
_reflns_number_gt                2376
_reflns_number_total             3560
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701559q-File006.cif
_cod_data_source_block           d5707
_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.

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

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'no' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023040