Regio- and Stereodivergent Allylic Reductions of Bicyclic Piperidine Enecarbamate Derivatives.
Berti, Francesco; Menichetti, Andrea; Favero, Lucilla; Marchetti, Fabio; Pineschi, Mauro; The Journal of organic chemistry 83 (2018) 12221–12228; doi:10.1021/acs.joc.8b01601

data_4035249
_publ_section_title
;
 Regio- and Stereodivergent Allylic Reductions of Bicyclic Piperidine
 Enecarbamate Derivatives.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12221
_journal_page_last               12228
_journal_paper_doi               10.1021/acs.joc.8b01601
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C20 H20 N2 O2'
_chemical_formula_sum            'C20 H20 N2 O2'
_chemical_formula_weight         320.38
_chemical_name_systematic
2-Phenyl-1-(9-phenyl-4-oxa-1,3-diaza-bicyclo[3.3.1]non-3-yl)-ethanone
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.584(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9704(3)
_cell_length_b                   6.5342(2)
_cell_length_c                   23.6337(7)
_cell_measurement_reflns_used    6824
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.30
_cell_measurement_theta_min      2.83
_cell_volume                     1659.62(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            19785
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.693
_diffrn_reflns_theta_min         3.240
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.204
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         5574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+0.1507P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1427
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3963
_reflns_number_total             5574
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01601_si_001.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035249
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              2866
_shelx_hkl_checksum              27732