Process for (<i>S</i>)-Ketamine and (<i>S</i>)-Norketamine via Resolution Combined with Racemization.
Gao, Shenghua; Gao, Xuezhi; Wu, Zenong; Li, Houyong; Yang, Zhezhou; Zhang, Fuli; The Journal of organic chemistry 85 (2020) 8656–8664; doi:10.1021/acs.joc.0c01090

data_4038508
_publ_section_title
;
 Process for (<i>S</i>)-Ketamine and (<i>S</i>)-Norketamine via Resolution
 Combined with Racemization.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8656
_journal_page_last               8664
_journal_paper_doi               10.1021/acs.joc.0c01090
_journal_volume                  85
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H13 Cl O2'
_chemical_formula_weight         224.67
_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   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2414(8)
_cell_length_b                   8.1329(8)
_cell_length_c                   18.752(3)
_cell_measurement_reflns_used    3845
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.964
_cell_measurement_theta_min      4.344
_cell_volume                     1104.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5396
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.988
_diffrn_reflns_theta_min         3.767
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
; 
 Flack x determined using 793 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0340P)^2^+0.0880P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0692
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2004
_reflns_number_total             2122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01090_si_002.cif
_cod_data_source_block           mo_d8v19706_0m
_cod_depositor_comments
'Adding full bibliography for 4038508--4038509.cif.'
_cod_database_code               4038508
_shelx_estimated_absorpt_t_min   0.938
_shelx_estimated_absorpt_t_max   0.959
_shelxl_version_number           2013-4
_shelx_res_checksum              93748
_shelx_hkl_checksum              49617