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_2018820
_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>anti</i>-(1<i>R</i>,2<i>S</i>,5<i>S</i>)-8-Benzyl-
2-[(<i>R</i>)-(4-bromophenyl)(hydroxy)methyl]-8-azabicyclo[3.2.1]octan-3-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.96905(4)
_cell_length_b                   14.76590(9)
_cell_length_c                   20.76083(13)
_cell_measurement_reflns_used    28586
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.6571
_cell_measurement_theta_min      2.7533
_cell_volume                     1829.83(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.064
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            67899
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    2.260
_exptl_absorpt_correction_T_max  0.816
_exptl_absorpt_correction_T_min  0.308
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.478
_refine_ls_abs_structure_details 'Flack (1983), with 2292 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.011(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         5359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0364P)^2^+1.3126P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                5007
_reflns_number_total             5359
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gz3222.cif
_cod_data_source_block           II
_cod_database_code               2018820
_cod_database_fobs_code          2018820