4α-Bromo-5α-cholestan-3β-ol and nor-5α-cholestan-3β-ol derivatives—stereoselective synthesis and hormonal activity in Caenorhabditis elegans
Martin, René; Saini, Ratni; Bauer, Ingmar; Gruner, Margit; Kataeva, Olga; Zagoriy, Vyacheslav; Entchev, Eugeni V.; Kurzchalia, Teymuras V.; Knölker, Hans-Joachim; Organic & Biomolecular Chemistry 7 (2009) 2303–2309; doi:10.1039/b904001c

data_7150677
_publ_section_title
;
 4\a-Bromo-5\a-cholestan-3\b-ol and nor-5\a-cholestan-3\b-ol
 derivatives---stereoselective synthesis and hormonal activity in
 Caenorhabditis elegans
;
_journal_issue                   11
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              2303
_journal_page_last               2309
_journal_paper_doi               10.1039/b904001c
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C27 H47 Br O'
_chemical_formula_sum            'C27 H47 Br O'
_chemical_formula_weight         467.56
_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                 110.66(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.802(1)
_cell_length_b                   7.528(1)
_cell_length_c                   15.271(2)
_cell_measurement_reflns_used    225
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      21.87
_cell_measurement_theta_min      4.44
_cell_volume                     1269.5(3)
_computing_cell_refinement       'Dirax/lsq (Duisenberg, 1992)'
_computing_data_collection       'Collect (Nonius BV, 1999)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)'
_computing_structure_refinement
'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      198(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       \f
_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  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            55589
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    1.634
_exptl_absorpt_correction_T_max  0.7253
_exptl_absorpt_correction_T_min  0.5936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.281
_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   -0.010(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         5973
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0268
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+0.1434P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0574
_refine_ls_wR_factor_ref         0.0611
_reflns_number_gt                5307
_reflns_number_total             5973
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b904001c.txt
_cod_data_source_block           kno4
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7150677