#------------------------------------------------------------------------------
#$Date: 2020-02-20 06:08:19 +0200 (Thu, 20 Feb 2020) $
#$Revision: 248304 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/99/7239966.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7239966
loop_
_publ_author_name
'Bredikhin, Alexander A.'
'Bredikhina, Zemfira A.'
'Gubaidullin, Aidar Timergalievich'
_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       'φ and ω 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/[σ²(Fo²)+(0.0362P)²+0.0368P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4914(3) 0.9770(4) -0.2190(2) 0.0153(5) Uani 1 1 d . . . . .
H11 H 0.3944 1.0406 -0.2238 0.018 Uiso 1 1 calc R U . . .
H12 H 0.5616 1.1130 -0.2029 0.018 Uiso 1 1 calc R U . . .
C2 C 0.5426(2) 0.7787(4) -0.1108(2) 0.0148(4) Uani 1 1 d . . . . .
H2 H 0.4856 0.7844 -0.0461 0.018 Uiso 1 1 calc R U . . .
C3 C 0.7025(2) 0.8044(4) -0.0370(2) 0.0158(5) Uani 1 1 d . . . . .
H31 H 0.7572 0.8079 -0.1026 0.019 Uiso 1 1 calc R U . . .
H32 H 0.7214 0.9582 0.0147 0.019 Uiso 1 1 calc R U . . .
C4 C 0.4988(2) 0.6018(4) -0.3190(2) 0.0144(5) Uani 1 1 d . . . . .
C5 C 0.8925(2) 0.6066(4) 0.1326(2) 0.0157(5) Uani 1 1 d . . . . .
C6 C 0.9345(2) 0.4218(4) 0.2305(2) 0.0167(5) Uani 1 1 d . . . . .
C7 C 1.0748(2) 0.4175(5) 0.3189(2) 0.0194(5) Uani 1 1 d . . . . .
H7 H 1.1035 0.2936 0.3854 0.023 Uiso 1 1 calc R U . . .
C8 C 1.1749(2) 0.5942(5) 0.3109(2) 0.0211(5) Uani 1 1 d . . . . .
H8 H 1.2706 0.5928 0.3734 0.025 Uiso 1 1 calc R U . . .
C9 C 1.1349(2) 0.7701(5) 0.2127(2) 0.0217(5) Uani 1 1 d . . . . .
H9 H 1.2038 0.8877 0.2058 0.026 Uiso 1 1 calc R U . . .
C10 C 0.9930(2) 0.7763(4) 0.1229(2) 0.0187(5) Uani 1 1 d . . . . .
H10 H 0.9657 0.8980 0.0549 0.022 Uiso 1 1 calc R U . . .
C11 C 0.8604(3) 0.0940(5) 0.3429(2) 0.0223(5) Uani 1 1 d . . . . .
H111 H 0.7775 -0.0142 0.3327 0.034 Uiso 1 1 calc R U . . .
H112 H 0.8792 0.1885 0.4263 0.034 Uiso 1 1 calc R U . . .
H113 H 0.9465 -0.0027 0.3471 0.034 Uiso 1 1 calc R U . . .
N1 N 0.4863(2) 0.8408(3) -0.33971(19) 0.0160(4) Uani 1 1 d . . . . .
O1 O 0.49415(17) 0.4389(3) -0.39893(14) 0.0193(4) Uani 1 1 d . . . . .
O2 O 0.51685(16) 0.5520(3) -0.18610(14) 0.0151(4) Uani 1 1 d . . . . .
O3 O 0.74920(15) 0.6030(3) 0.05291(14) 0.0174(4) Uani 1 1 d . . . . .
O4 O 0.82836(15) 0.2554(3) 0.22958(14) 0.0190(4) Uani 1 1 d . . . . .
H1 H 0.481(3) 0.903(5) -0.419(3) 0.031(7) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 100.57(17) . . ?
N1 C1 H11 111.7 . . ?
C2 C1 H11 111.7 . . ?
N1 C1 H12 111.7 . . ?
C2 C1 H12 111.7 . . ?
H11 C1 H12 109.4 . . ?
O2 C2 C3 109.25(17) . . ?
O2 C2 C1 104.70(15) . . ?
C3 C2 C1 110.43(19) . . ?
O2 C2 H2 110.8 . . ?
C3 C2 H2 110.8 . . ?
C1 C2 H2 110.8 . . ?
O3 C3 C2 108.79(18) . . ?
O3 C3 H31 109.9 . . ?
C2 C3 H31 109.9 . . ?
O3 C3 H32 109.9 . . ?
C2 C3 H32 109.9 . . ?
H31 C3 H32 108.3 . . ?
O1 C4 N1 129.5(2) . . ?
O1 C4 O2 120.8(2) . . ?
N1 C4 O2 109.7(2) . . ?
O3 C5 C10 124.6(2) . . ?
O3 C5 C6 115.61(19) . . ?
C10 C5 C6 119.74(19) . . ?
O4 C6 C7 124.7(2) . . ?
O4 C6 C5 115.70(18) . . ?
C7 C6 C5 119.6(2) . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 120.2(2) . . ?
C5 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
O4 C11 H111 109.5 . . ?
O4 C11 H112 109.5 . . ?
H111 C11 H112 109.5 . . ?
O4 C11 H113 109.5 . . ?
H111 C11 H113 109.5 . . ?
H112 C11 H113 109.5 . . ?
C4 N1 C1 113.16(19) . . ?
C4 N1 H1 120.5(19) . . ?
C1 N1 H1 126.2(19) . . ?
C4 O2 C2 108.67(16) . . ?
C5 O3 C3 115.71(17) . . ?
C6 O4 C11 116.26(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.453(3) . ?
C1 C2 1.536(3) . ?
C1 H11 0.9900 . ?
C1 H12 0.9900 . ?
C2 O2 1.454(3) . ?
C2 C3 1.503(3) . ?
C2 H2 1.0000 . ?
C3 O3 1.430(2) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 O1 1.216(3) . ?
C4 N1 1.333(3) . ?
C4 O2 1.369(2) . ?
C5 O3 1.374(2) . ?
C5 C10 1.378(3) . ?
C5 C6 1.407(3) . ?
C6 O4 1.376(3) . ?
C6 C7 1.381(3) . ?
C7 C8 1.396(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 O4 1.432(2) . ?
C11 H111 0.9800 . ?
C11 H112 0.9800 . ?
C11 H113 0.9800 . ?
N1 H1 0.88(3) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O2 -16.68(19) . . . . ?
N1 C1 C2 C3 100.8(2) . . . . ?
O2 C2 C3 O3 -59.5(2) . . . . ?
C1 C2 C3 O3 -174.15(15) . . . . ?
O3 C5 C6 O4 2.8(3) . . . . ?
C10 C5 C6 O4 -177.74(19) . . . . ?
O3 C5 C6 C7 -177.23(19) . . . . ?
C10 C5 C6 C7 2.2(3) . . . . ?
O4 C6 C7 C8 179.6(2) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C6 C7 C8 C9 -1.6(3) . . . . ?
C7 C8 C9 C10 1.7(3) . . . . ?
O3 C5 C10 C9 177.3(2) . . . . ?
C6 C5 C10 C9 -2.1(3) . . . . ?
C8 C9 C10 C5 0.2(3) . . . . ?
O1 C4 N1 C1 177.4(2) . . . . ?
O2 C4 N1 C1 -1.5(3) . . . . ?
C2 C1 N1 C4 11.7(2) . . . . ?
O1 C4 O2 C2 170.59(18) . . . . ?
N1 C4 O2 C2 -10.4(2) . . . . ?
C3 C2 O2 C4 -101.10(19) . . . . ?
C1 C2 O2 C4 17.2(2) . . . . ?
C10 C5 O3 C3 -5.6(3) . . . . ?
C6 C5 O3 C3 173.80(18) . . . . ?
C2 C3 O3 C5 -177.10(17) . . . . ?
C7 C6 O4 C11 11.2(3) . . . . ?
C5 C6 O4 C11 -168.92(18) . . . . ?
