Effects of nitric acid concentration for nitration of fused [1,2,5]oxadiazolo[3,4-d]pyrimidine-5,7-diamine
Shreeve, Jean'ne M.; Chinnam, Ajay Kumar; Tang, Yongxing; Staples, Richard J.; Dalton Transactions  (2022) –; doi:10.1039/D2DT03255D

data_7711745
_publ_section_title
;
 Effects of nitric acid concentration for nitration of fused
 [1,2,5]oxadiazolo[3,4-d]pyrimidine-5,7-diamine
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT03255D
_journal_year                    2022
_chemical_formula_moiety         'C4 H6 N5 O3, N O3'
_chemical_formula_sum            'C4 H6 N6 O6'
_chemical_formula_weight         234.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-16
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2022-08-01 deposited with the CCDC.	2022-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.7205(2)
_cell_length_b                   8.76982(17)
_cell_length_c                   15.3669(2)
_cell_measurement_reflns_used    4718
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.6220
_cell_measurement_theta_min      5.7050
_cell_volume                     1714.28(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_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    127.00 167.00   0.50    0.96    --  113.25  61.00 -30.00   80
  2  \w    139.00 178.00   0.50    0.96    --  113.25  61.00  90.00   78
  3  \w    108.00 159.00   0.50    0.96    --  113.25 106.00   7.00  102
  4  \w    132.00 158.00   0.50    0.96    --  113.25  22.00-109.00   52
  5  \w     46.00  71.00   0.50    0.96    --  113.25 -94.00  30.00   50
  6  \w     68.00  96.00   0.50    0.96    --  113.25 -94.00   0.00   56
  7  \w     49.00 107.00   0.50    0.96    --  113.25-118.00   7.00  116
  8  \w     42.00  67.00   0.50    0.96    --  113.25 -61.00 150.00   50
  9  \w     42.00  67.00   0.50    0.96    --  113.25 -61.00  60.00   50
 10  \w     42.00  67.00   0.50    0.96    --  113.25 -61.00  30.00   50
 11  \w     45.00  70.00   0.50    0.96    --  113.25 -61.00   0.00   50
 12  \w     43.00  68.00   0.50    0.96    --  113.25 -61.00 -90.00   50
 13  \w     43.00  70.00   0.50    0.96    --  113.25 -61.00-120.00   54
 14  \w     44.00  69.00   0.50    0.96    --  113.25 -61.00-180.00   50
 15  \w    -18.00  25.00   0.50    0.24    --  -48.10  19.00  30.00   86
 16  \w    -27.00   7.00   0.50    0.24    --  -48.10  19.00 -60.00   68
 17  \w    -23.00  21.00   0.50    0.24    --  -48.10  22.00-109.00   88
 18  \w    -83.00 -45.00   0.50    0.24    --  -48.10 125.00   0.00   76
 19  \w    -47.00 -21.00   0.50    0.96    --  -91.75 118.00  93.00   52
 20  \w   -157.00-131.00   0.50    0.96    --  -91.75 -77.00  30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0767030000
_diffrn_orient_matrix_UB_12      -0.1269934000
_diffrn_orient_matrix_UB_13      0.0278677000
_diffrn_orient_matrix_UB_21      0.0922946000
_diffrn_orient_matrix_UB_22      0.1131520000
_diffrn_orient_matrix_UB_23      -0.0059420000
_diffrn_orient_matrix_UB_31      -0.0164633000
_diffrn_orient_matrix_UB_32      0.0438382000
_diffrn_orient_matrix_UB_33      0.0961090000
_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  0.0306
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7126
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.760
_diffrn_reflns_theta_min         5.758
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.505
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.00064(12)
_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   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         1815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0362P)^2^+0.9211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0805
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1641
_reflns_number_total             1815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt03255d2.cif
_cod_data_source_block           js11221d
_cod_original_cell_volume        1714.27(5)
_cod_database_code               7711745
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C4H5N6O5.5
_chemical_oxdiff_usercomment     A33C
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.838
_olex2_refinement_description
;
;
_shelx_res_checksum              60812
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id A33C
_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 1.099
_oxdiff_exptl_absorpt_empirical_full_min 0.905