Synthesis of environmentally friendly energetic cocrystal derived from commodity chemicals.
Inoue, Kazuki; Nishiwaki, Yosuke; Kumasaki, Mieko; Matsumoto, Shinya; Okada, Ken; Chemical communications (Cambridge, England) 60 (2024) 13963–13966; doi:10.1039/d4cc04037f

data_7133943
_publ_section_title
;
 Synthesis of environmentally friendly energetic cocrystal derived from
 commodity chemicals.
;
_journal_issue                   94
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13963
_journal_page_last               13966
_journal_paper_doi               10.1039/d4cc04037f
_journal_volume                  60
_journal_year                    2024
_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_name_systematic        'glysine ammonium nitrate'
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-23
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-23 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.015(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.77620(10)
_cell_length_b                   22.1425(4)
_cell_length_c                   7.91350(10)
_cell_measurement_reflns_used    3418
_cell_measurement_temperature    223
_cell_measurement_theta_max      74.4900
_cell_measurement_theta_min      3.9790
_cell_volume                     1011.51(3)
_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)'
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w     54.00  81.00   0.50    0.50    --    0.00  38.00 -90.00   54
  2  \w     18.00  80.00   0.50    0.50    --    0.00  57.00  90.00  124
  3  \w    -29.00  20.00   0.50    0.50    --    0.00  38.00 -90.00   98
  4  \w     22.00 133.00   0.50    0.99    --   96.60 -82.00 -60.00  222
  5  \w     67.00 141.00   0.50    0.99    --   96.60  61.00  60.00  148
  6  \w     39.00  72.00   0.50    0.99    --   96.60 -82.00   0.00   66
  7  \w    104.00 185.00   0.50    0.99    --   96.60  61.00 -30.00  162
  8  \w     74.00 100.00   0.50    0.99    --   96.60  61.00 -30.00   52
  9  \w     92.00 129.00   0.50    0.99    --   96.60 -82.00   0.00   74
 10  \w     89.00 186.00   0.50    0.99    --   96.60  61.00  90.00  194
 11  \w    116.00 141.00   0.50    0.99    --   96.60  61.00 150.00   50
 12  \w     74.00 100.00   0.50    0.99    --   96.60 -77.00-150.00   52
 13  \w     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       '\w 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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_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_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_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
_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+0.001xFc^2^\l^3^/sin(2\q)]^-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_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0334
_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/[\s^2^(Fo^2^)+(0.0522P)^2^+0.0881P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1803
_reflns_number_total             2007
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04037f2.cif
_cod_data_source_block           20230419gly-an-11
_cod_depositor_comments          'Adding full bibliography for 7133943.cif.'
_cod_database_code               7133943
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.874
_shelx_estimated_absorpt_t_min   0.820
_olex2_refinement_description
;
;
_shelx_res_checksum              36956
_shelx_hkl_checksum              90451
_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