Enantioselective hydrogenation of annulated arenes: controlled formation of multiple stereocenters in adjacent rings
Wiesenfeldt, Mario P.; Moock, Daniel; Paul, Daniel; Glorius, Frank; Chemical Science 12 (2021) 5611–5615; doi:10.1039/D0SC07099H

data_1560813
_publ_section_title
;
 Enantioselective hydrogenation of annulated arenes: controlled formation
 of multiple stereocenters in adjacent rings
;
_journal_issue                   15
_journal_name_full               'Chemical Science'
_journal_page_first              5611
_journal_page_last               5615
_journal_paper_doi               10.1039/D0SC07099H
_journal_volume                  12
_journal_year                    2021
_chemical_formula_sum            'C10 H18 N2 O'
_chemical_formula_weight         182.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'APEX3 v2016.1-0'
_audit_update_record
;
2020-05-27 deposited with the CCDC.	2021-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.743(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8352(5)
_cell_length_b                   9.3209(4)
_cell_length_c                   11.4836(6)
_cell_measurement_reflns_used    3813
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.3913
_cell_measurement_theta_min      5.1655
_cell_volume                     996.91(9)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14466
_diffrn_reflns_theta_full        66.72
_diffrn_reflns_theta_max         66.72
_diffrn_reflns_theta_min         5.17
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+0.3186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                1334
_reflns_number_total             1752
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc07099h2.cif
_cod_data_source_block           glo9476
_cod_depositor_comments
'Adding full bibliography for 1560813--1560814.cif.'
_cod_database_code               1560813
_shelx_res_checksum              47545
_shelx_hkl_checksum              76552