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_1560814
_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_absolute_configuration ad
_chemical_formula_sum            'C10 H20 Cl2 N2 O'
_chemical_formula_weight         255.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 106.642(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3482(5)
_cell_length_b                   6.0629(3)
_cell_length_c                   13.2849(9)
_cell_measurement_reflns_used    1130
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      4.08
_cell_volume                     644.24(7)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection
;

Collect (Nonius B.V., 1998)
;
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'rotating anode Nonius FR591'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4170
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         4.22
_diffrn_source                   'Mo rotating anode'
_diffrn_source_type              'Mo rotating anode'
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.271
_refine_ls_abs_structure_details
;

Flack x determined using 645 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1959
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0577
_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^)+(0.0782P)^2^+0.9832P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1517
_reflns_number_gt                1802
_reflns_number_total             1959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc07099h2.cif
_cod_data_source_block           glo9508
_cod_depositor_comments
'Adding full bibliography for 1560813--1560814.cif.'
_cod_database_code               1560814
_shelx_res_checksum              20681
_shelx_hkl_checksum              40840