Relative configuration, absolute configuration and absolute structure of three isomeric 8-benzyl-2-[(4-bromophenyl)(hydroxy)methyl]-8-azabicyclo[3.2.1]octan-3-ones
Brzezinski, Krzysztof; Lazny, Ryszard; Nodzewska, Aneta; Sidorowicz, Katarzyna; Acta Crystallographica Section C 69 (2013) 303–306; doi:10.1107/S0108270113002503

data_2018819
_publ_section_title
;
 Relative configuration, absolute configuration and absolute structure of
 three isomeric
 8-benzyl-2-[(4-bromophenyl)(hydroxy)methyl]-8-azabicyclo[3.2.1]octan-3-ones
;
_journal_coeditor_code           GZ3222
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              303
_journal_page_last               306
_journal_paper_doi               10.1107/S0108270113002503
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C21 H22 Br N O2'
_chemical_formula_moiety         'C21 H22 Br N O2'
_chemical_formula_sum            'C21 H22 Br N O2'
_chemical_formula_weight         400.31
_chemical_name_systematic
;
(+-)-<i>exo</i>,<i>syn</i>-(1<i>RS</i>,2<i>SR</i>,5<i>SR</i>)-8-Benzyl-2-
[(<i>SR</i>)-(4-bromophenyl)(hydroxy)methyl]-8-azabicyclo[3.2.1]octan-3-one
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   29.8145(5)
_cell_length_b                   29.8145(5)
_cell_length_c                   10.2028(2)
_cell_measurement_reflns_used    11027
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.5084
_cell_measurement_theta_min      2.7272
_cell_volume                     7854.3(2)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_molecular_graphics    'OLEX2 (Dolomanov <i>et al.</i>, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4052
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer (Cu at zero) with Atlas detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24029
_diffrn_reflns_theta_full        29.57
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    2.364
_exptl_absorpt_correction_T_max  0.633
_exptl_absorpt_correction_T_min  0.434
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3708
_exptl_crystal_size_max          0.5376
_exptl_crystal_size_mid          0.4637
_exptl_crystal_size_min          0.2905
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.665
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0333P)^2^+18.6115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0814
_reflns_number_gt                4130
_reflns_number_total             4885
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gz3222.cif
_cod_data_source_block           I
_cod_original_cell_volume        7854.2(4)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2018819
_cod_database_fobs_code          2018819