# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_20230419gly-an-11
_database_code_depnum_ccdc_archive 'CCDC 2257499'
loop_
_audit_author_name
_audit_author_address
'Shinya Matsumoto'
;Yokohama National University
Japan
;
_audit_update_record             
;
2024-07-23 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;
_audit_creation_date             2024-07-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'glysine ammonium nitrate'
_chemical_formula_moiety         'C2 H5 N O2, 2(N O3), 2(H4 N)'
_chemical_formula_sum            'C2 H13 N5 O8'
_chemical_formula_weight         235.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   5.77620(10)
_cell_length_b                   22.1425(4)
_cell_length_c                   7.91350(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.015(2)
_cell_angle_gamma                90
_cell_volume                     1011.51(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3418
_cell_measurement_temperature    223
_cell_measurement_theta_max      74.4900
_cell_measurement_theta_min      3.9790
_shelx_estimated_absorpt_T_max   0.874
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    1.378
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.66a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_preparation       'cocrystallization by cooling method'
_exptl_crystal_recrystallization_method 'cooling method using water solvent'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5369
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.237
_diffrn_reflns_theta_min         3.993
_diffrn_ambient_temperature      223.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     54.00  81.00   0.50    0.50    --    0.00  38.00 -90.00   54
  2  ω     18.00  80.00   0.50    0.50    --    0.00  57.00  90.00  124
  3  ω    -29.00  20.00   0.50    0.50    --    0.00  38.00 -90.00   98
  4  ω     22.00 133.00   0.50    0.99    --   96.60 -82.00 -60.00  222
  5  ω     67.00 141.00   0.50    0.99    --   96.60  61.00  60.00  148
  6  ω     39.00  72.00   0.50    0.99    --   96.60 -82.00   0.00   66
  7  ω    104.00 185.00   0.50    0.99    --   96.60  61.00 -30.00  162
  8  ω     74.00 100.00   0.50    0.99    --   96.60  61.00 -30.00   52
  9  ω     92.00 129.00   0.50    0.99    --   96.60 -82.00   0.00   74
 10  ω     89.00 186.00   0.50    0.99    --   96.60  61.00  90.00  194
 11  ω    116.00 141.00   0.50    0.99    --   96.60  61.00 150.00   50
 12  ω     74.00 100.00   0.50    0.99    --   96.60 -77.00-150.00   52
 13  ω     74.00  99.00   0.50    0.99    --   96.60  61.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0043050000
_diffrn_orient_matrix_UB_12      0.0690818000
_diffrn_orient_matrix_UB_13      0.0228014000
_diffrn_orient_matrix_UB_21      -0.1114431000
_diffrn_orient_matrix_UB_22      0.0078098000
_diffrn_orient_matrix_UB_23      -0.1783423000
_diffrn_orient_matrix_UB_31      -0.2425668000
_diffrn_orient_matrix_UB_32      -0.0023827000
_diffrn_orient_matrix_UB_33      0.0748460000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_special_details          223
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1803
_reflns_number_total             2007
_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 1.171.40.66a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0089(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2007
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.074
_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)+(0.0522P)²+0.0881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0954
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.33043(15) 0.66842(4) 0.67793(10) 0.0320(2) Uani 1 1 d . . . . .
O2 O 0.45120(15) 0.57958(4) 0.58310(11) 0.0357(2) Uani 1 1 d . . . . .
O3 O -0.02935(18) 0.54041(4) 0.17767(12) 0.0432(3) Uani 1 1 d . . . . .
O6 O 0.85873(19) 0.72590(5) 1.10388(12) 0.0474(3) Uani 1 1 d . . . . .
O7 O 1.07025(18) 0.68878(5) 1.30855(13) 0.0500(3) Uani 1 1 d . . . . .
O4 O 0.1309(2) 0.59439(5) -0.01327(13) 0.0551(3) Uani 1 1 d . . . . .
N1 N -0.11974(19) 0.63896(5) 0.65640(15) 0.0332(3) Uani 1 1 d . . . . .
N4 N 0.3687(2) 0.71788(6) 1.00788(15) 0.0352(3) Uani 1 1 d . . . . .
O8 O 0.6986(2) 0.67840(6) 1.30861(14) 0.0589(3) Uani 1 1 d . . . . .
O5 O -0.2404(2) 0.58042(6) -0.02356(14) 0.0571(3) Uani 1 1 d . . . . .
N5 N 0.8750(2) 0.69758(5) 1.24205(14) 0.0363(3) Uani 1 1 d . . . . .
N3 N -0.0456(2) 0.57210(5) 0.04663(13) 0.0388(3) Uani 1 1 d . . . . .
N2 N 0.4688(3) 0.53389(6) 0.24877(17) 0.0404(3) Uani 1 1 d . . . . .
C2 C 0.2956(2) 0.61663(5) 0.62292(13) 0.0265(3) Uani 1 1 d . . . . .
C1 C 0.0481(2) 0.59439(5) 0.59666(16) 0.0297(3) Uani 1 1 d . . . . .
H1A H -0.109(3) 0.6406(9) 0.767(3) 0.060(5) Uiso 1 1 d . . . . .
H1B H -0.088(3) 0.6746(9) 0.615(2) 0.048(5) Uiso 1 1 d . . . . .
H1C H -0.261(4) 0.6269(8) 0.628(2) 0.059(5) Uiso 1 1 d . . . . .
H1D H 0.021(3) 0.5571(7) 0.6554(19) 0.038(4) Uiso 1 1 d . . . . .
H1E H 0.016(3) 0.5871(7) 0.4798(19) 0.039(4) Uiso 1 1 d . . . . .
H2A H 0.470(3) 0.5558(9) 0.344(3) 0.061(5) Uiso 1 1 d . . . . .
H4A H 0.347(4) 0.6985(9) 0.904(3) 0.069(6) Uiso 1 1 d . . . . .
H2B H 0.494(3) 0.4946(10) 0.278(2) 0.062(6) Uiso 1 1 d . . . . .
H2C H 0.567(4) 0.5455(11) 0.181(3) 0.081(7) Uiso 1 1 d . . . . .
H4B H 0.516(5) 0.7168(11) 1.043(3) 0.087(7) Uiso 1 1 d . . . . .
H2D H 0.325(5) 0.5394(11) 0.202(3) 0.089(8) Uiso 1 1 d . . . . .
H4C H 0.285(5) 0.6991(12) 1.082(3) 0.093(8) Uiso 1 1 d . . . . .
H4D H 0.341(5) 0.7552(14) 0.997(3) 0.100(8) Uiso 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
O1 C2 1.2404(14) . ?
O2 C2 1.2650(14) . ?
O3 N3 1.2529(14) . ?
O6 N5 1.2612(14) . ?
O7 N5 1.2428(15) . ?
O4 N3 1.2419(15) . ?
N1 C1 1.4729(16) . ?
N1 H1A 0.88(2) . ?
N1 H1B 0.876(19) . ?
N1 H1C 0.88(2) . ?
N4 H4A 0.93(2) . ?
N4 H4B 0.89(3) . ?
N4 H4C 0.88(3) . ?
N4 H4D 0.85(3) . ?
O8 N5 1.2386(16) . ?
O5 N3 1.2510(16) . ?
N2 H2A 0.90(2) . ?
N2 H2B 0.91(2) . ?
N2 H2C 0.83(3) . ?
N2 H2D 0.90(3) . ?
C2 C1 1.5195(16) . ?
C1 H1D 0.963(16) . ?
C1 H1E 0.950(15) . ?

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
C1 N1 H1A 109.0(12) . . ?
C1 N1 H1B 109.5(11) . . ?
C1 N1 H1C 109.2(12) . . ?
H1A N1 H1B 109.3(16) . . ?
H1A N1 H1C 107.4(17) . . ?
H1B N1 H1C 112.4(16) . . ?
H4A N4 H4B 111(2) . . ?
H4A N4 H4C 109(2) . . ?
H4A N4 H4D 110(2) . . ?
H4B N4 H4C 109(2) . . ?
H4B N4 H4D 104(2) . . ?
H4C N4 H4D 115(2) . . ?
O7 N5 O6 118.96(12) . . ?
O8 N5 O6 120.11(11) . . ?
O8 N5 O7 120.93(12) . . ?
O4 N3 O3 119.99(12) . . ?
O4 N3 O5 120.66(12) . . ?
O5 N3 O3 119.35(12) . . ?
H2A N2 H2B 107.7(17) . . ?
H2A N2 H2C 113(2) . . ?
H2A N2 H2D 105(2) . . ?
H2B N2 H2C 111(2) . . ?
H2B N2 H2D 112(2) . . ?
H2C N2 H2D 109(2) . . ?
O1 C2 O2 125.38(11) . . ?
O1 C2 C1 119.20(10) . . ?
O2 C2 C1 115.41(10) . . ?
N1 C1 C2 111.44(10) . . ?
N1 C1 H1D 107.4(9) . . ?
N1 C1 H1E 108.7(9) . . ?
C2 C1 H1D 112.4(9) . . ?
C2 C1 H1E 109.6(9) . . ?
H1D C1 H1E 107.2(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 C2 C1 N1 -4.53(15) . . . . ?
O2 C2 C1 N1 176.40(10) . . . . ?

_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 2.256
_oxdiff_exptl_absorpt_empirical_full_min 0.591
