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_7711744
_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 H2 Cs N7 O3'
_chemical_formula_sum            'C4 H2 Cs N7 O3'
_chemical_formula_weight         329.04
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-15
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-01 deposited with the CCDC.	2022-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                111.928(2)
_cell_angle_beta                 103.0549(18)
_cell_angle_gamma                106.0137(17)
_cell_formula_units_Z            2
_cell_length_a                   7.72210(14)
_cell_length_b                   8.01862(17)
_cell_length_c                   8.13576(19)
_cell_measurement_reflns_used    6703
_cell_measurement_temperature    100.00(18)
_cell_measurement_theta_max      79.7580
_cell_measurement_theta_min      6.3190
_cell_volume                     417.51(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.62a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.62a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.62a (Rigaku OD, 2022)'
_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(18)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_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      5.00  30.00   0.50    0.05    --   14.00  44.00 -48.82   50
  2  \w      5.00  31.00   0.50    0.05    --   18.00  43.00   6.98   52
  3  \w      2.00  30.00   0.50    0.05    --   14.00  42.00 130.51   56
  4  \w     42.00  68.00   0.50    0.05    --   47.62  30.00 170.71   52
  5  \w     35.00  60.00   0.50    0.05    --   47.62  31.00  86.49   50
  6  \w     52.00 101.00   0.50    0.05    --  113.25 -77.00 -60.00   98
  7  \w     42.00  67.00   0.50    0.05    --  113.25 -61.00 -30.00   50
  8  \w     42.00  67.00   0.50    0.05    --  113.25 -61.00  30.00   50
  9  \w     42.00  68.00   0.50    0.05    --  113.25 -61.00  60.00   52
 10  \w     43.00  68.00   0.50    0.05    --  113.25 -61.00 150.00   50
 11  \w     -7.00  19.00   0.50    0.05    --    2.00 -61.00 166.75   52
 12  \w     42.00  67.00   0.50    0.05    --  113.25 -61.00 -60.00   50
 13  \w     43.00  69.00   0.50    0.05    --  113.25 -61.00-120.00   52
 14  \w     79.00 104.00   0.50    0.05    --  113.25 -94.00 -60.00   50
 15  \w     51.00 110.00   0.50    0.05    --  113.25-129.00 -72.00  118
 16  \w     43.00  85.00   0.50    0.05    --   47.62-129.00 -72.00   84
 17  \w     74.00 100.00   0.50    0.05    --  113.25-125.00 -90.00   52
 18  \w     55.00  95.00   0.50    0.05    --  113.25-125.00  60.00   80
 19  \w     73.00  99.00   0.50    0.05    --  113.25-140.00 114.00   52
 20  \w     46.00 105.00   0.50    0.05    --  113.25-125.00 150.00  118
 21  \w     42.00 102.00   0.50    0.05    --  113.25 -94.00 150.00  120
 22  \w     50.00 102.00   0.50    0.05    --   47.62-140.00 114.00  104
 23  \w     69.00  98.00   0.50    0.05    --  113.25 -94.00 120.00   58
 24  \w     46.00  71.00   0.50    0.05    --  113.25-125.00 -30.00   50
 25  \w     77.00 108.00   0.50    0.05    --  113.25-125.00 -30.00   62
 26  \w     67.00 108.00   0.50    0.05    --  113.25-125.00-120.00   82
 27  \w     48.00  74.00   0.50    0.05    --  113.25 -94.00 -60.00   52
 28  \w     76.00 101.00   0.50    0.05    --  113.25 -94.00  30.00   50
 29  \w     42.00  90.00   0.50    0.05    --  113.25 -94.00  60.00   96
 30  \w    105.00 136.00   0.50    0.05    --  113.25  30.00 150.00   62
 31  \w    142.00 169.00   0.50    0.05    --  113.25  61.00 120.00   54
 32  \w    147.00 178.00   0.50    0.05    --  113.25  61.00  90.00   62
 33  \w    142.00 172.00   0.50    0.05    --  113.25  61.00  60.00   60
 34  \w    123.00 165.00   0.50    0.05    --  113.25  45.00  30.00   84
 35  \w    122.00 178.00   0.50    0.05    --  113.25  45.00 150.00  112
 36  \w    152.00 177.00   0.50    0.05    --  113.25  77.00 -30.00   50
 37  \w    103.00 166.00   0.50    0.05    --  113.25  30.00   0.00  126
 38  \w    101.00 136.00   0.50    0.05    --  113.25  30.00 -30.00   70
 39  \w    127.00 169.00   0.50    0.05    --  113.25  61.00-150.00   84
 40  \w    134.00 178.00   0.50    0.05    --  113.25  45.00-180.00   88
 41  \w    122.00 148.00   0.50    0.05    --  113.25  45.00-150.00   52
 42  \w    153.00 178.00   0.50    0.05    --  113.25  30.00 -30.00   50
 43  \w    101.00 155.00   0.50    0.05    --  113.25  30.00 -90.00  108
 44  \w    101.00 155.00   0.50    0.05    --  113.25  30.00 -60.00  108
 45  \w    105.00 142.00   0.50    0.05    --  113.25  30.00-150.00   74
 46  \w    116.00 144.00   0.50    0.05    --  113.25  30.00  30.00   56
 47  \w    101.00 142.00   0.50    0.05    --  113.25  30.00  90.00   82
 48  \w    104.00 129.00   0.50    0.05    --  113.25  30.00 120.00   50
 49  \w    153.00 178.00   0.50    0.05    --  113.25  30.00 150.00   50
 50  \w    104.00 129.00   0.50    0.05    --  113.25 140.00 173.00   50
 51  \w    134.00 160.00   0.50    0.05    --  113.25 129.00   0.00   52
 52  \w    112.00 138.00   0.50    0.05    --  113.25 125.00 -30.00   52
 53  \w    107.00 145.00   0.50    0.05    --  113.25 125.00 -90.00   76
 54  \w    -61.00 -35.00   0.50    0.05    --  -47.62 140.00 173.00   52
 55  \w    -66.00 -17.00   0.50    0.05    --  -47.62 129.00   0.00   98
 56  \w    -63.00 -38.00   0.50    0.05    --  -91.75 129.00   0.00   50
 57  \w    -57.00 -29.00   0.50    0.05    --  -42.00 -32.00 129.76   56
 58  \w    -64.00 -39.00   0.50    0.05    --  -47.62 -31.00  85.25   50
 59  \w    -36.00 -11.00   0.50    0.05    --  -22.00 -39.00 -14.07   50
 60  \w    -60.00 -35.00   0.50    0.05    --  -47.62 -19.00 -90.00   50
 61  \w   -116.00 -90.00   0.50    0.05    --  -47.62 -19.00 -90.00   52
 62  \w    -76.00 -45.00   0.50    0.05    --  -58.00 -30.00  28.29   62
 63  \w    -83.00 -46.00   0.50    0.05    --  -58.00 -30.00  -5.00   74
 64  \w   -123.00 -97.00   0.50    0.05    --  -58.00 -30.00  -5.00   52
 65  \w   -116.00 -90.00   0.50    0.05    --  -91.75 -30.00  90.00   52
 66  \w   -154.00-129.00   0.50    0.05    --  -82.00 -30.00 -34.93   50
 67  \w   -143.00 -88.00   0.50    0.05    --  -91.75 -30.00  67.02  110
 68  \w   -100.00 -70.00   0.50    0.05    --  -82.00 -30.00 -34.93   60
 69  \w   -105.00 -71.00   0.50    0.05    --  -82.00 -30.00 -64.52   68
 70  \w    -92.00 -45.00   0.50    0.05    --  -58.00 -30.00-166.65   94
 71  \w   -117.00 -88.00   0.50    0.05    --  -91.75 -30.00-150.00   58
 72  \w   -127.00 -93.00   0.50    0.05    --  -70.00 -28.00-129.94   68
 73  \w    -87.00 -58.00   0.50    0.05    --  -70.00 -28.00-129.94   58
 74  \w    -86.00 -54.00   0.50    0.05    --  -66.00 -29.00 -82.22   64
 75  \w    -97.00 -66.00   0.50    0.05    --  -78.00 -28.00  -3.94   62
 76  \w    -83.00 -56.00   0.50    0.05    --  -66.00 -29.00  77.55   54
 77  \w    -80.00 -48.00   0.50    0.05    --  -62.00 -28.00 115.56   64
 78  \w   -104.00 -78.00   0.50    0.05    --  -91.75 -28.00 104.83   52
 79  \w   -107.00 -82.00   0.50    0.05    --  -91.75 -27.00 135.06   50
 80  \w   -123.00 -98.00   0.50    0.05    --  -91.75 -30.00 171.65   50
 81  \w   -134.00-104.00   0.50    0.05    --  -62.00 -28.00 115.56   60
 82  \w   -165.00-136.00   0.50    0.05    --  -91.75 -28.00 104.83   58
 83  \w   -109.00 -67.00   0.50    0.05    --  -78.00 -24.00 159.18   84
 84  \w   -122.00 -96.00   0.50    0.05    --  -66.00 -27.00 -33.54   52
 85  \w    -82.00 -53.00   0.50    0.05    --  -66.00 -27.00 -33.54   58
 86  \w    -91.00 -66.00   0.50    0.05    --  -78.00 -27.00-113.11   50
 87  \w   -104.00 -79.00   0.50    0.05    --  -91.75 -26.00-108.19   50
 88  \w   -141.00-116.00   0.50    0.05    --  -91.75-129.00 -72.00   50
 89  \w   -106.00 -78.00   0.50    0.05    --  -47.62-140.00 114.00   56
 90  \w   -120.00 -94.00   0.50    0.05    --  -91.75-140.00 114.00   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      -0.0571177000
_diffrn_orient_matrix_UB_12      0.0300811000
_diffrn_orient_matrix_UB_13      -0.1776751000
_diffrn_orient_matrix_UB_21      0.0470146000
_diffrn_orient_matrix_UB_22      0.2169068000
_diffrn_orient_matrix_UB_23      0.1287634000
_diffrn_orient_matrix_UB_31      0.2106906000
_diffrn_orient_matrix_UB_32      0.0551571000
_diffrn_orient_matrix_UB_33      0.0089549000
_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  0.0439
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8527
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.935
_diffrn_reflns_theta_min         6.309
_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    34.722
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.086
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.62a (Rigaku Oxford Diffraction, 2022)
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    2.617
_exptl_crystal_description       irregular
_exptl_crystal_F_000             308
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.019
_refine_diff_density_max         0.757
_refine_diff_density_min         -1.999
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1778
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0256
_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^)+(0.0414P)^2^+0.6788P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1760
_reflns_number_total             1778
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt03255d2.cif
_cod_data_source_block           js722d
_cod_original_cell_volume        417.516(17)
_cod_database_code               7711744
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C4H2CsN7O3
_chemical_oxdiff_usercomment     A33-Cs
_shelx_estimated_absorpt_t_max   0.558
_shelx_estimated_absorpt_t_min   0.051
_olex2_refinement_description
;
;
_shelx_res_checksum              83530
_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 A33-Cs
_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 1.464
_oxdiff_exptl_absorpt_empirical_full_min 0.789