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_1565045
_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 H15 Cl N O3'
_chemical_formula_sum            'C18 H15 Cl N O3'
_chemical_formula_weight         328.76
_chemical_name_common            1c
_chemical_name_systematic
1-(6-(4-chlorophenyl)-2,3-dihydro-4H-1,4-oxazin-4-yl)-2-phenylethan-1-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-07-12 deposited with the CCDC.	2021-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5094(2)
_cell_length_b                   14.3271(4)
_cell_length_c                   19.9017(6)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      68.00
_cell_measurement_theta_min      3.80
_cell_volume                     1570.92(9)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0523
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23942
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.165
_diffrn_reflns_theta_min         3.801
_exptl_absorpt_coefficient_mu    2.280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       block
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.6407
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1015 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0607P)^2^+0.1779P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0996
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2642
_reflns_number_total             2883
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04288b2.cif
_cod_data_source_block           ta_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1565045
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.634
_shelx_estimated_absorpt_t_max   0.684
_shelx_res_checksum              20389
_shelx_hkl_checksum              9877