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_7711743
_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 H3 N7 O3'
_chemical_formula_sum            'C4 H3 N7 O3'
_chemical_formula_weight         197.13
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-13
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2021.04.04 svn.r0348f7ac for OlexSys, GUI svn.r6303)
;
_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            4
_cell_length_a                   13.2552(15)
_cell_length_b                   6.7087(8)
_cell_length_c                   7.6337(7)
_cell_measurement_reflns_used    1857
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.1000
_cell_measurement_theta_min      4.0380
_cell_volume                     678.83(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.100a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.100a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.100a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (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(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.793
_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    -49.00   7.00   0.50   27.48    --    4.99 -48.00 123.00  112
  2  \w    -16.00  10.00   0.50   27.48    --   -5.53 -77.00 -17.00   52
  3  \w      0.00  25.00   0.50   27.48    --    4.99 -77.00-180.00   50
  4  \w      0.00  25.00   0.50   27.48    --    4.99 -77.00-150.00   50
  5  \w      2.00  28.00   0.50   27.48    --    4.99 -77.00 -30.00   52
  6  \w    -28.00  -3.00   0.50   27.48    --   -5.53  77.00 -60.00   50
;
_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      -0.0312221000
_diffrn_orient_matrix_UB_12      0.0618860000
_diffrn_orient_matrix_UB_13      -0.0522499000
_diffrn_orient_matrix_UB_21      0.0418447000
_diffrn_orient_matrix_UB_22      0.0631879000
_diffrn_orient_matrix_UB_23      -0.0171248000
_diffrn_orient_matrix_UB_31      0.0121866000
_diffrn_orient_matrix_UB_32      -0.0576687000
_diffrn_orient_matrix_UB_33      -0.0748487000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.793
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3343
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.793
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.021
_diffrn_reflns_theta_min         4.044
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.100a (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    1.929
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.055
_refine_diff_density_max         1.246
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1298P)^2^+0.3532P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1683
_refine_ls_wR_factor_ref         0.1845
_reflns_Friedel_coverage         0.000
_reflns_number_gt                727
_reflns_number_total             931
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt03255d2.cif
_cod_data_source_block           js321dmo
_cod_database_code               7711743
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C4H87N9O6
_chemical_oxdiff_usercomment     A-33
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.981
_reflns_odcompleteness_completeness 98.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N4(H4)
2.b X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
;
_shelx_res_checksum              87701
_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 A-33
_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 1.714
_oxdiff_exptl_absorpt_empirical_full_min 0.804