# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2015_09_09_dt_alpha-gly_d
_database_code_depnum_ccdc_archive 'CCDC 2083500'
loop_
_audit_author_name
_audit_author_address
'Damian Trzybinski'
;Biological and Chemical Research Centre University of Warsaw
Poland
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;
_audit_creation_date             2021-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H5 N O2'
_chemical_formula_sum            'C2 H5 N O2'
_chemical_formula_weight         75.07
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
_chemical_oxdiff_usercomment     ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.0867(2)
_cell_length_b                   11.7982(4)
_cell_length_c                   5.4598(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.983(5)
_cell_angle_gamma                90
_cell_volume                     303.84(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2421
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.1190
_cell_measurement_theta_min      3.4450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             160
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4778
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.505
_diffrn_reflns_theta_min         3.454
_diffrn_ambient_environment      N~1~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0026
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -49.00   1.00    3.00    --  -29.20-160.00-150.00   54
  2  ω   -103.00 -49.00   1.00    3.00    --  -29.20-160.00 150.00   54
  3  ω    -61.00  44.00   1.00    3.00    --  -29.20  37.00-150.00  105
  4  ω   -100.00  -6.00   1.00    3.00    --  -29.20 -57.00  60.00   94
  5  ω   -103.00 -49.00   1.00    3.00    --  -29.20-160.00 -60.00   54
  6  ω   -100.00  -6.00   1.00    3.00    --  -29.20 -57.00-150.00   94
  7  ω   -100.00  -6.00   1.00    3.00    --  -29.20 -57.00 -60.00   94
  8  ω   -100.00  -6.00   1.00    3.00    --  -29.20 -57.00 120.00   94
  9  ω   -109.00 -81.00   1.00    3.00    --  -29.20 160.00   0.00   28
 10  ω    -35.00  -6.00   1.00    3.00    --   29.36 132.00 -14.89   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1398664000
_diffrn_orient_matrix_UB_12      0.0094233000
_diffrn_orient_matrix_UB_13      0.0920511000
_diffrn_orient_matrix_UB_21      0.0331034000
_diffrn_orient_matrix_UB_22      0.0292657000
_diffrn_orient_matrix_UB_23      -0.0983003000
_diffrn_orient_matrix_UB_31      -0.0442156000
_diffrn_orient_matrix_UB_32      0.0516392000
_diffrn_orient_matrix_UB_33      0.0388900000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                809
_reflns_number_total             932
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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)'
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         932
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+0.1369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0841
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All O(H,H,H) groups
2. Restrained distances
 N1-H1B
 0.87 with sigma of 0.01
 N1-H1A
 0.87 with sigma of 0.01
 N1-H1C
 0.87 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C2(H2B,H2A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.5696(2) 0.62502(8) 0.56586(18) 0.00818(19) Uani 1 1 d . . . . .
C2 C 0.5584(2) 0.64580(8) 0.28596(18) 0.00905(19) Uani 1 1 d . . . . .
H2B H 0.379772 0.617813 0.159667 0.011 Uiso 1 1 calc R . . . .
H2A H 0.567251 0.726645 0.257616 0.011 Uiso 1 1 calc R . . . .
N1 N 0.79557(18) 0.58871(7) 0.24048(16) 0.00949(18) Uani 1 1 d D . . . .
O1 O 0.80249(15) 0.59374(6) 0.73640(13) 0.01085(18) Uani 1 1 d . . . . .
O2 O 0.34510(15) 0.64236(6) 0.60647(14) 0.01171(18) Uani 1 1 d . . . . .
H1A H 0.789(3) 0.5160(8) 0.272(3) 0.014 Uiso 1 1 d DR . . . .
H1B H 0.963(2) 0.6148(11) 0.346(2) 0.014 Uiso 1 1 d DR . . . .
H1C H 0.789(3) 0.5980(12) 0.0757(19) 0.014 Uiso 1 1 d DR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C2 1.5275(13) . ?
C1 O1 1.2572(11) . ?
C1 O2 1.2590(12) . ?
C2 H2B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 N1 1.4817(12) . ?
N1 H1A 0.878(9) . ?
N1 H1B 0.886(9) . ?
N1 H1C 0.894(8) . ?

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
O1 C1 C2 117.40(8) . . ?
O1 C1 O2 125.63(9) . . ?
O2 C1 C2 116.96(8) . . ?
C1 C2 H2B 109.3 . . ?
C1 C2 H2A 109.3 . . ?
H2B C2 H2A 108.0 . . ?
N1 C2 C1 111.52(7) . . ?
N1 C2 H2B 109.3 . . ?
N1 C2 H2A 109.3 . . ?
C2 N1 H1A 108.6(9) . . ?
C2 N1 H1B 112.1(9) . . ?
C2 N1 H1C 112.6(9) . . ?
H1A N1 H1B 108.1(13) . . ?
H1A N1 H1C 109.0(13) . . ?
H1B N1 H1C 106.3(13) . . ?

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
O1 C1 C2 N1 19.48(12) . . . . ?
O2 C1 C2 N1 -161.51(8) . . . . ?

_olex2_date_sample_data_collection 2015-09-09
_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 1.527
_oxdiff_exptl_absorpt_empirical_full_min 0.774
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2016_09_29_dt_b-gly_d
_database_code_depnum_ccdc_archive 'CCDC 2083501'
loop_
_audit_author_name
_audit_author_address
'Damian Trzybinski'
;Biological and Chemical Research Centre University of Warsaw
Poland
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;
_audit_creation_date             2021-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H5 N O2'
_chemical_formula_sum            'C2 H5 N O2'
_chemical_formula_weight         75.07
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
_chemical_oxdiff_usercomment     ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.0757(2)
_cell_length_b                   6.1737(2)
_cell_length_c                   5.3882(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.422(4)
_cell_angle_gamma                90
_cell_volume                     154.931(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7569
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.4690
_cell_measurement_theta_min      4.1100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             80
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9425
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.489
_diffrn_reflns_theta_min         4.122
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0026
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00 102.00   1.00   16.50    --   29.20  77.00 -30.00  106
  2  ω     21.00 109.00   1.00   16.50    --   29.20-160.00 150.00   88
  3  ω     -4.00 102.00   1.00   16.50    --   29.20  77.00-120.00  106
  4  ω     -4.00 102.00   1.00   16.50    --   29.20  77.00  60.00  106
  5  ω     21.00 109.00   1.00   16.50    --   29.20-160.00 -30.00   88
  6  ω     -4.00 102.00   1.00   16.50    --   29.20  77.00 150.00  106
  7  ω   -104.00 -49.00   1.00   16.50    --  -29.36-160.00  30.00   55
  8  ω   -104.00 -49.00   1.00   16.50    --  -29.36-160.00-150.00   55
  9  ω   -104.00  46.00   1.00   16.50    --  -29.36   0.00-120.00  150
 10  ω   -104.00  46.00   1.00   16.50    --  -29.36   0.00  60.00  150
 11  ω     49.00 103.00   1.00   16.50    --   29.20 160.00 120.00   54
 12  ω     -1.00 102.00   1.00   16.50    --   29.20  39.00-153.00  103
 13  ω    -46.00 104.00   1.00   16.50    --   29.20   0.00-180.00  150
 14  ω    -46.00 104.00   1.00   16.50    --   29.20   0.00-150.00  150
 15  ω    -46.00 104.00   1.00   16.50    --   29.20   0.00-120.00  150
 16  ω    -46.00 104.00   1.00   16.50    --   29.20   0.00 -90.00  150
 17  ω    -46.00 104.00   1.00   16.50    --   29.20   0.00 -60.00  150
 18  ω     49.00 103.00   1.00   16.50    --   29.20 160.00 -60.00   54
 19  ω    -46.00 104.00   1.00   16.50    --   29.20   0.00   0.00  150
 20  ω    -46.00 104.00   1.00   16.50    --   29.20   0.00  30.00  150
 21  ω    -46.00 104.00   1.00   16.50    --   29.20   0.00  60.00  150
 22  ω    -46.00  15.00   1.00   16.50    --   29.20   0.00  90.00   61
 23  ω    -46.00 104.00   1.00   16.50    --   29.20   0.00 -30.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0174620000
_diffrn_orient_matrix_UB_12      0.0365213000
_diffrn_orient_matrix_UB_13      0.1173579000
_diffrn_orient_matrix_UB_21      0.1358886000
_diffrn_orient_matrix_UB_22      -0.0440451000
_diffrn_orient_matrix_UB_23      0.0822356000
_diffrn_orient_matrix_UB_31      0.0665108000
_diffrn_orient_matrix_UB_32      0.0996248000
_diffrn_orient_matrix_UB_33      -0.0066449000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                931
_reflns_number_total             942
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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)'
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 423 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         942
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0229
_refine_ls_restrained_S_all      1.098
_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)+(0.0321P)²+0.0406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0642
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H,H) groups
2. Restrained distances
 N1-H1B
 0.87 with sigma of 0.01
 N1-H1C
 0.87 with sigma of 0.01
 N1-H1A
 0.87 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.6365(2) 0.5374(2) 0.5601(2) 0.0086(2) Uani 1 1 d . . . . .
C2 C 0.6131(2) 0.5500(2) 0.2684(2) 0.0096(2) Uani 1 1 d . . . . .
H2A H 0.432586 0.486161 0.148573 0.012 Uiso 1 1 calc R . . . .
H2B H 0.613217 0.700680 0.217560 0.012 Uiso 1 1 calc R . . . .
N1 N 0.8531(2) 0.4355(2) 0.2350(2) 0.0091(2) Uani 1 1 d D . . . .
H1A H 1.019(3) 0.480(3) 0.349(3) 0.011 Uiso 1 1 d DR . . . .
H1B H 0.859(4) 0.454(3) 0.076(3) 0.011 Uiso 1 1 d DR . . . .
H1C H 0.837(4) 0.298(2) 0.257(4) 0.011 Uiso 1 1 d DR . . . .
O1 O 0.8829(2) 0.50817(18) 0.74215(18) 0.0120(2) Uani 1 1 d . . . . .
O2 O 0.40959(19) 0.56505(17) 0.59711(18) 0.0108(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C2 1.5303(16) . ?
C1 O1 1.2582(15) . ?
C1 O2 1.2565(14) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N1 1.4801(16) . ?
N1 H1A 0.866(12) . ?
N1 H1B 0.874(12) . ?
N1 H1C 0.866(12) . ?

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
O1 C1 C2 117.10(10) . . ?
O2 C1 C2 117.01(10) . . ?
O2 C1 O1 125.83(11) . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N1 C2 C1 111.65(9) . . ?
N1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C2 N1 H1A 112.0(13) . . ?
C2 N1 H1B 113.9(14) . . ?
C2 N1 H1C 108.8(13) . . ?
H1A N1 H1B 104.8(19) . . ?
H1A N1 H1C 109.4(19) . . ?
H1B N1 H1C 107.7(19) . . ?

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
O1 C1 C2 N1 24.55(16) . . . . ?
O2 C1 C2 N1 -158.00(11) . . . . ?

_olex2_date_sample_data_collection 2016-09-29
_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 1.444
_oxdiff_exptl_absorpt_empirical_full_min 0.351
