Asymmetric Hydrogenation for the Synthesis of 2-Substituted Chiral Morpholines
Li, Mingxu; Zhang, Jian; Zou, Yashi; Zhou, Fengfan; Zhang, Zhenfeng; Zhang, Wanbin; Chemical Science  (2021) –; doi:10.1039/D1SC04288B

data_1565044
_publ_section_title
;
 Asymmetric Hydrogenation for the Synthesis of 2-Substituted Chiral
 Morpholines
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04288B
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H18 F N O3'
_chemical_formula_sum            'C18 H18 F N O3'
_chemical_formula_weight         315.33
_chemical_name_common            2b
_chemical_name_systematic
'Benzyl (R)-2-(4-fluorophenyl)morpholine-4-carboxylate'
_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   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-07-10 deposited with the CCDC.	2021-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.18(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.798(3)
_cell_length_b                   8.047(2)
_cell_length_c                   11.933(7)
_cell_measurement_reflns_used    6597
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.89
_cell_volume                     802.7(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10998
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.421
_diffrn_reflns_theta_min         3.899
_exptl_absorpt_coefficient_mu    0.801
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.6720
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details
;
 Flack x determined using 1162 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0509P)^2^+0.0546P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0888
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2709
_reflns_number_total             2929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04288b2.cif
_cod_data_source_block           t_a
_cod_original_cell_volume        802.7(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1565044
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.869
_shelx_estimated_absorpt_t_max   0.896
_shelx_res_checksum              41589
_shelx_hkl_checksum              49685