Enzyme-mediated synthesis and crystal structure of (2R,4S)-hydroxyketamine, C13H16ClNO2
Reiss, Guido J.; Urlacher, Vlada B.; Luelf, U. Joost; Zeitschrift für Kristallographie - New Crystal Structures 235 (2020) 1037–1039; doi:10.1515/ncrs-2020-0157

data_8105371
_publ_section_title
;
 Enzyme-mediated synthesis and crystal structure of
 (2R,4S)-hydroxyketamine, C13H16ClNO2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              1037
_journal_page_last               1039
_journal_paper_doi               10.1515/ncrs-2020-0157
_journal_volume                  235
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H16 Cl N O2'
_chemical_formula_sum            'C13 H16 Cl N O2'
_chemical_formula_weight         253.72
_chemical_name_common
;
(2R,4S)-hydroxyketamine 
;
_chemical_name_systematic
;
(2R,4S)-2-(2-chlorophenyl)-4-hydroxy-2-methylamino)-cyclohexanone
;
_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           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 92.555(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4945(7)
_cell_length_b                   7.2336(6)
_cell_length_c                   11.5401(10)
_cell_measurement_reflns_used    3667
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      30.96
_cell_measurement_theta_min      3.18
_cell_volume                     624.99(10)
_computing_cell_refinement       'Bruker APEX2/SAINT'
_computing_data_collection       'Bruker APEX2/SAINT'
_computing_data_reduction        'Bruker APEX2/SAINT'
_computing_molecular_graphics    ' Diamond 4.0'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0873
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6118
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         1.766
_diffrn_source                   'Incoatec IMS 2.0'
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.800
_exptl_crystal_size_min          0.560
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1306 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_coef       0.019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3527
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0200P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0947
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                3225
_reflns_number_total             3527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2020-0157_suppl.cif
_cod_data_source_block           HKetamine
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'None' was changed
to 'none' in accordance with the built-in table derived from the CIF
Core dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               8105371
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.777
_shelx_estimated_absorpt_t_max   0.852