Chirality-Dependent Supramolecular Synthons based on the 1,3-Oxazolidin-2-one Framework: Chiral Drugs Mephenoxalone, Metaxalone and other 114 examples
Bredikhin, Alexander A.; Bredikhina, Zemfira A.; Gubaidullin, Aidar Timergalievich; CrystEngComm  (2020) –; doi:10.1039/D0CE00116C

data_7239966
_publ_section_title
;
 Chirality-Dependent Supramolecular Synthons based on the
 1,3-Oxazolidin-2-one Framework: Chiral Drugs Mephenoxalone, Metaxalone
 and other 114 examples
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00116C
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C11 H13 N O4'
_chemical_formula_sum            'C11 H13 N O4'
_chemical_formula_weight         223.22
_chemical_melting_point          399.0(10)
_chemical_name_common            (R)-mephenoxalone
_chemical_name_systematic        (R)-5-(2-methoxyphenoxymethyl)-2-oxazolidinones
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-06-11 deposited with the CCDC.	2020-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.560(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7048(7)
_cell_length_b                   5.5085(4)
_cell_length_c                   10.4326(7)
_cell_measurement_reflns_used    3956
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      4.01
_cell_volume                     528.71(7)
_computing_cell_refinement       'APEX2 v2008.6-1 (Bruker AXS)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9737
_diffrn_reflns_theta_full        28.000
_diffrn_reflns_theta_max         30.608
_diffrn_reflns_theta_min         3.472
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_correction_T_min  0.9002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
Siemens Area Detector Absorption Correction Program.
Bruker AXS. Madison. Wisconsin. USA
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             236
_exptl_crystal_recrystallization_method
'slow evaporation of sample solutions from a mixture of CHCl3/CCl4'
_exptl_crystal_size_max          0.760
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0362P)^2^+0.0368P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0811
_reflns_number_gt                2181
_reflns_number_total             2692
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00116c2.cif
_cod_data_source_block           R-2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '398-400' was changed to
'399.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7239966
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              784