#------------------------------------------------------------------------------
#$Date: 2019-12-14 03:15:32 +0200 (Sat, 14 Dec 2019) $
#$Revision: 245171 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/76/4037664.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_4037664
loop_
_publ_author_name
'Brunner, Henri'
'Tsuno, Takashi'
'Balázs, Gábor'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -74.00 -40.00   0.50   23.27    --   20.00  54.00 -60.00   68
  2  ω    -34.00  -8.00   0.50   23.27    --   20.00  54.00 -60.00   52
  3  ω     23.00 108.00   0.50   23.27    --   20.00  54.00 -60.00  170
  4  ω    -73.00 -12.00   0.50   23.27    --   20.00  54.00 150.00  122
  5  ω     19.00  57.00   0.50   23.27    --   20.00  54.00 150.00   76
  6  ω    -42.00  -7.00   0.50   23.27    --   20.00  54.00  90.00   70
  7  ω     -5.00  21.00   0.50   23.27    --   20.00  54.00  90.00   52
  8  ω     51.00  95.00   0.50   23.27    --   20.00  54.00  90.00   88
  9  ω    -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       'ω 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/[σ²(Fo²)+(0.0425P)²+1.3869P] where P=(Fo²+2Fc²)/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 > 2σ(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'
_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.
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Cl01 Cl 1.02462(8) 0.38336(5) 0.25276(12) 0.0223(2) Uani 1 1 d .
O002 O 0.6293(3) 0.31285(18) 0.9740(4) 0.0275(5) Uani 1 1 d .
O003 O 0.4440(3) 0.4084(2) 0.7284(5) 0.0332(6) Uani 1 1 d .
N004 N 0.8665(3) 0.35605(18) 0.7100(4) 0.0182(4) Uani 1 1 d .
H00A H 0.931039 0.375758 0.607573 0.022 Uiso 1 1 calc GR
H00B H 0.855761 0.285390 0.706850 0.022 Uiso 1 1 calc GR
H00C H 0.909500 0.376800 0.857351 0.022 Uiso 1 1 calc GR
C005 C 0.5918(3) 0.3687(2) 0.8022(5) 0.0201(5) Uani 1 1 d .
C006 C 0.7059(3) 0.4061(2) 0.6407(5) 0.0206(5) Uani 1 1 d .
H00D H 0.662351 0.387830 0.475914 0.025 Uiso 1 1 calc R
H00E H 0.716696 0.483093 0.651335 0.025 Uiso 1 1 calc R
C007 C 0.3201(4) 0.3790(3) 0.8688(7) 0.0374(8) Uani 1 1 d .
H00F H 0.230686 0.427677 0.835130 0.056 Uiso 1 1 calc GR
H00G H 0.364717 0.382034 1.036430 0.056 Uiso 1 1 calc GR
H00H H 0.283184 0.307825 0.827631 0.056 Uiso 1 1 calc GR
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'
Cl Cl 0.1484 0.1585 '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
C005 O003 C007 116.2(3)
O002 C005 O003 125.2(3)
O002 C005 C006 124.7(3)
O003 C005 C006 110.1(2)
N004 C006 C005 110.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O002 C005 1.196(4)
O003 C005 1.334(4)
O003 C007 1.454(4)
N004 C006 1.476(3)
C005 C006 1.502(4)
