Synthesis and solid state characterization of molecular rotors with steroidal stators: ethisterone and norethisterone.
Rodríguez-Molina, Braulio; Pozos, Arturo; Cruz, Ricardo; Romero, Margarita; Flores, Blas; Farfán, Noberto; Santillan, Rosa; Garcia-Garibay, Miguel A; Organic & biomolecular chemistry 8 (2010) 2993–3000; doi:10.1039/c003778h

data_7153367
_publ_section_title
;
 Synthesis and solid state characterization of molecular rotors with
 steroidal stators: ethisterone and norethisterone.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2993
_journal_page_last               3000
_journal_paper_doi               10.1039/c003778h
_journal_volume                  8
_journal_year                    2010
_chemical_absolute_configuration rm
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C50 H58 O6, 2(C H Cl3)'
_chemical_formula_sum            'C52 H60 Cl6 O6'
_chemical_formula_weight         993.70
_chemical_name_systematic
;
1,4-bis(19-nor-17a-ethynyltestosterone-17b-acetate)phenylene
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2009-12-19T22:39:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.896(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   19.2269(6)
_cell_length_b                   10.7806(4)
_cell_length_c                   12.2170(4)
_cell_measurement_reflns_used    9786
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.103
_cell_measurement_theta_min      2.91
_cell_measurement_wavelength     0.71073
_cell_volume                     2523.07(15)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.792779E-1
_diffrn_orient_matrix_UB_12      0.301469E-1
_diffrn_orient_matrix_UB_13      -0.472761E-1
_diffrn_orient_matrix_UB_21      0.679062E-1
_diffrn_orient_matrix_UB_22      0.424515E-1
_diffrn_orient_matrix_UB_23      0.662782E-1
_diffrn_orient_matrix_UB_31      -0.18945E-2
_diffrn_orient_matrix_UB_32      -0.928273E-1
_diffrn_orient_matrix_UB_33      0.110116E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15648
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        27.15
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         4.72
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.3
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1044.0
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5379
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.127
_refine_ls_R_factor_gt           0.0644
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0801P)^2^+1.3026P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.18
_reflns_number_gt                3144
_reflns_number_total             5379
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c003778h.txt
_cod_data_source_block           Compound1
_cod_original_sg_symbol_Hall     'C2 y'
_cod_original_sg_symbol_H-M      C2
_cod_database_code               7153367