Chiral Selectivity in the Achiral Amino Acid Glycine.
Brunner, Henri; Tsuno, Takashi; Balázs, Gábor; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02726

data_4037664
_publ_section_title
;
 Chiral Selectivity in the Achiral Amino Acid Glycine.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02726
_journal_year                    2019
_chemical_formula_moiety         'Cl, C3 H8 N O2'
_chemical_formula_sum            'C3 H8 Cl N O2'
_chemical_formula_weight         125.55
_chemical_name_systematic        'Methyl glycinate hydrochloride'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.548(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3685(3)
_cell_length_b                   12.5338(4)
_cell_length_c                   5.6550(2)
_cell_measurement_reflns_used    2649
_cell_measurement_temperature    173
_cell_measurement_theta_max      30.4100
_cell_measurement_theta_min      2.9440
_cell_volume                     584.93(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'Rigaku HyPix-3000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -74.00 -40.00   0.50   23.27    --   20.00  54.00 -60.00   68
  2  \w    -34.00  -8.00   0.50   23.27    --   20.00  54.00 -60.00   52
  3  \w     23.00 108.00   0.50   23.27    --   20.00  54.00 -60.00  170
  4  \w    -73.00 -12.00   0.50   23.27    --   20.00  54.00 150.00  122
  5  \w     19.00  57.00   0.50   23.27    --   20.00  54.00 150.00   76
  6  \w    -42.00  -7.00   0.50   23.27    --   20.00  54.00  90.00   70
  7  \w     -5.00  21.00   0.50   23.27    --   20.00  54.00  90.00   52
  8  \w     51.00  95.00   0.50   23.27    --   20.00  54.00  90.00   88
  9  \w    -73.00 108.00   0.50   23.27    --   20.00  54.00  30.00  362
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB mini2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0228989000
_diffrn_orient_matrix_UB_12      -0.0183621000
_diffrn_orient_matrix_UB_13      0.1194457000
_diffrn_orient_matrix_UB_21      0.0737654000
_diffrn_orient_matrix_UB_22      0.0287317000
_diffrn_orient_matrix_UB_23      0.0093152000
_diffrn_orient_matrix_UB_31      -0.0376958000
_diffrn_orient_matrix_UB_32      0.0451955000
_diffrn_orient_matrix_UB_33      0.0425823000
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5320
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.487
_diffrn_reflns_theta_min         2.468
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.549
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_preparation       'from TCI'
_exptl_crystal_recrystallization_method 'Crystallization from H2O/DMSO/THF'
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.127
_refine_diff_density_max         1.522
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.247
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     66
_refine_ls_number_reflns         1707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.247
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0425P)^2^+1.3869P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1534
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1468
_reflns_number_total             1707
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02726_si_002.cif
_cod_data_source_block           CCDC1916163
_cod_database_code               4037664
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C3 H8 Cl1 N1 O2'
_chemical_oxdiff_usercomment     'Me glycine HCl'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C006(H00D,H00E)
2.b Idealised Me refined as rotating group:
 N004(H00A,H00B,H00C), C007(H00F,H00G,H00H)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.044
_oxdiff_exptl_absorpt_empirical_full_min 0.979