Mono-N-oxidation of heterocycle-fused pyrimidines.
Tang, Yongxing; Li, Kejia; Chinnam, Ajay Kumar; Staples, Richard J.; Shreeve, Jean'ne M.; Dalton transactions (Cambridge, England : 2003) 50 (2021) 2143–2148; doi:10.1039/d0dt03260c

data_7706459
_publ_section_title
;
 Mono-N-oxidation of heterocycle-fused pyrimidines.
;
_journal_issue                   6
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2143
_journal_page_last               2148
_journal_paper_doi               10.1039/d0dt03260c
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         '2(Cl), C5 H8 N6 O'
_chemical_formula_sum            'C5 H8 Cl2 N6 O'
_chemical_formula_weight         239.07
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-26
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.10.11 svn.r5b043f8a for OlexSys, GUI svn.r6175)
;
_audit_update_record
;
2020-10-27 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                79.811(2)
_cell_angle_beta                 75.385(2)
_cell_angle_gamma                76.143(2)
_cell_formula_units_Z            2
_cell_length_a                   6.3903(2)
_cell_length_b                   7.8053(2)
_cell_length_c                   9.9575(2)
_cell_measurement_reflns_used    5784
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.7140
_cell_measurement_theta_min      8.3850
_cell_volume                     463.01(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-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      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.958
_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  31.00   0.50    0.05    --   14.00  43.00  42.27   52
  2  \w    137.00 172.00   0.50    0.20    --  107.11  57.00  90.00   70
  3  \w    115.00 165.00   0.50    0.20    --  107.11  37.00 120.00  100
  4  \w    117.00 154.00   0.50    0.20    --  107.11  37.00  60.00   74
  5  \w    126.00 167.00   0.50    0.20    --  107.11  77.00   0.00   82
  6  \w    122.00 151.00   0.50    0.20    --  107.11  37.00 -90.00   58
  7  \w    105.00 155.00   0.50    0.20    --  107.11  19.00  30.00  100
  8  \w    114.00 176.00   0.50    0.20    --  107.11  37.00-120.00  124
  9  \w    128.00 174.00   0.50    0.20    --  107.11  77.00-180.00   92
 10  \w    105.00 149.00   0.50    0.20    --  107.11  19.00-180.00   88
 11  \w     77.00 103.00   0.50    0.20    --   86.00  29.00-177.42   52
 12  \w    -23.00  18.00   0.50    0.05    --  -47.57  19.00-150.00   82
 13  \w    -86.00 -61.00   0.50    0.05    --  -47.57 147.00 -72.00   50
 14  \w    -66.00 -26.00   0.50    0.20    --  -86.25  57.00 120.00   80
 15  \w    -72.00 -47.00   0.50    0.20    --  -86.25 124.00 123.00   50
 16  \w    -81.00 -36.00   0.50    0.05    --  -47.57 124.00 123.00   90
 17  \w     36.00  97.00   0.50    0.20    --  107.11 -99.00-120.00  122
 18  \w     36.00 102.00   0.50    0.20    --  107.11-125.00-180.00  132
 19  \w     51.00 124.00   0.50    0.20    --  107.11-147.00-121.00  146
 20  \w     75.00 100.00   0.50    0.05    --   47.57-147.00-121.00   50
 21  \w     46.00 105.00   0.50    0.20    --  107.11-125.00   0.00  118
 22  \w     77.00 103.00   0.50    0.20    --  107.11 -99.00 -30.00   52
 23  \w     64.00 108.00   0.50    0.20    --  107.11-124.00  43.00   88
 24  \w     81.00 107.00   0.50    0.20    --  107.11-125.00  90.00   52
 25  \w     47.00  78.00   0.50    0.20    --  107.11-125.00  90.00   62
 26  \w     54.00  80.00   0.50    0.05    --   47.57-124.00  43.00   52
 27  \w     35.00  65.00   0.50    0.20    --  107.11 -57.00   0.00   60
 28  \w     39.00  64.00   0.50    0.20    --  107.11 -57.00  60.00   50
 29  \w     35.00  61.00   0.50    0.20    --  107.11 -57.00  90.00   52
 30  \w    -18.00  25.00   0.50    0.05    --   47.57 -19.00  30.00   86
 31  \w     39.00  65.00   0.50    0.20    --  107.11 -57.00-150.00   52
 32  \w     99.00 124.00   0.50    0.20    --  107.11 147.00 -72.00   50
 33  \w    107.00 177.00   0.50    0.20    --  107.11 125.00  30.00  140
 34  \w    101.00 151.00   0.50    0.20    --  107.11 124.00 123.00  100
 35  \w    -91.00 -39.00   0.50    0.05    --  -47.57 -25.00  65.75  104
 36  \w    -36.00 -11.00   0.50    0.05    --  -22.00 -40.00 -24.66   50
 37  \w    -30.00  -1.00   0.50    0.05    --  -14.00 -43.00 -67.59   58
 38  \w    -47.00 -21.00   0.50    0.05    --  -34.00 -34.00-118.57   52
 39  \w    -54.00 -29.00   0.50    0.05    --  -42.00 -33.00 -57.50   50
 40  \w    -58.00 -33.00   0.50    0.05    --  -42.00 -32.00-129.89   50
 41  \w    -17.00   9.00   0.50    0.05    --   -6.00 -55.00  15.65   52
 42  \w    -40.00 -15.00   0.50    0.05    --  -26.00 -38.00  98.23   50
 43  \w    -39.00 -13.00   0.50    0.05    --  -26.00 -38.00 149.19   52
 44  \w    -64.00 -39.00   0.50    0.05    --  -46.00 -31.00  91.42   50
 45  \w    -94.00 -36.00   0.50    0.05    --  -47.57 -30.00-160.65  116
 46  \w   -138.00 -73.00   0.50    0.20    --  -86.25 -25.00 -67.35  130
 47  \w   -145.00-107.00   0.50    0.20    --  -70.00 -29.00   0.53   76
 48  \w    -95.00 -69.00   0.50    0.20    --  -82.00 -30.00 -21.88   52
 49  \w    -86.00 -61.00   0.50    0.20    --  -74.00 -29.00  53.16   50
 50  \w   -127.00-101.00   0.50    0.20    --  -74.00 -29.00  53.16   52
 51  \w   -122.00 -97.00   0.50    0.05    --  -58.00 -30.00 167.08   50
 52  \w    -85.00 -49.00   0.50    0.05    --  -58.00 -30.00 167.08   72
 53  \w   -110.00 -80.00   0.50    0.20    --  -86.25 -29.00 163.45   60
 54  \w   -120.00 -69.00   0.50    0.20    --  -82.00 -30.00 136.51  102
 55  \w   -125.00 -80.00   0.50    0.20    --  -86.25 -29.00  31.90   90
 56  \w    -93.00 -58.00   0.50    0.20    --  -70.00 -29.00  41.34   70
 57  \w    -88.00 -57.00   0.50    0.20    --  -70.00 -29.00   0.53   62
 58  \w   -106.00 -74.00   0.50    0.20    --  -86.25 -29.00 -71.03   64
 59  \w    -92.00 -63.00   0.50    0.20    --  -74.00 -29.00-120.66   58
 60  \w   -111.00 -75.00   0.50    0.20    --  -86.25 -29.00-140.56   72
 61  \w   -129.00 -81.00   0.50    0.20    --  -86.25 -29.00-164.21   96
 62  \w   -161.00-125.00   0.50    0.20    --  -86.25 -27.00 -36.46   72
 63  \w   -106.00 -74.00   0.50    0.20    --  -86.25 -26.00 -99.60   64
 64  \w   -115.00 -80.00   0.50    0.20    --  -86.25 -27.00 -36.46   70
 65  \w   -136.00-110.00   0.50    0.20    --  -86.25 -26.00 -99.60   52
 66  \w   -125.00 -99.00   0.50    0.20    --  -86.25 -28.00  45.00   52
 67  \w    -98.00 -73.00   0.50    0.20    --  -86.25 -28.00  45.00   50
 68  \w   -150.00 -73.00   0.50    0.20    --  -86.25 -28.00  98.35  154
 69  \w   -129.00-104.00   0.50    0.20    --  -86.25-124.00  43.00   50
 70  \w    -90.00 -65.00   0.50    0.05    --  -47.57-147.00-121.00   50
 71  \w   -145.00 -78.00   0.50    0.20    --  -86.25-147.00-121.00  134
 72  \w    -51.00 -25.00   0.50    0.20    --  -86.25 118.00 135.00   52
 73  \w    -27.00  -2.00   0.50    0.05    --  -14.00 -46.00 139.98   50
 74  \w      5.00  30.00   0.50    0.05    --   18.00  43.00-105.47   50
 75  \w    -45.00 -20.00   0.50    0.05    --  -30.00 -36.00-174.33   50
 76  \w     18.00  43.00   0.50    0.05    --   30.00  36.00  65.67   50
 77  \w    -47.00 -22.00   0.50    0.05    --  -34.00 -35.00  56.12   50
 78  \w    -27.00   4.00   0.50    0.05    --  -47.57  19.00-180.00   62
 79  \w     54.00  81.00   0.50    0.05    --   47.57 -99.00-150.00   54
 80  \w     18.00  44.00   0.50    0.05    --   47.57 -99.00-150.00   52
 81  \w    -70.00 -45.00   0.50    0.05    --  -58.00 -30.00 134.66   50
 82  \w   -128.00-102.00   0.50    0.20    --  -70.00 -29.00  62.41   52
 83  \w    -82.00 -57.00   0.50    0.20    --  -70.00 -29.00  62.41   50
 84  \w    -86.00 -61.00   0.50    0.20    --  -74.00 -29.00  20.48   50
 85  \w    -88.00 -62.00   0.50    0.20    --  -74.00 -29.00 -14.19   52
 86  \w    -43.00 -18.00   0.50    0.20    --  -86.25  37.00  60.00   50
 87  \w   -110.00 -84.00   0.50    0.20    --  -86.25 -28.00   9.61   52
 88  \w   -141.00-115.00   0.50    0.20    --  -86.25-125.00-150.00   52
 89  \w    153.00 178.00   0.50    0.20    --  107.11  19.00 -30.00   50
 90  \w     36.00  84.00   0.50    0.20    --  107.11 -99.00  90.00   96
 91  \w     96.00 122.00   0.50    0.20    --  107.11  19.00 -30.00   52
 92  \w    145.00 171.00   0.50    0.20    --  107.11  37.00-180.00   52
 93  \w     35.00  60.00   0.50    0.20    --  107.11 -57.00-180.00   50
 94  \w    114.00 140.00   0.50    0.20    --  107.11  37.00-180.00   52
 95  \w    108.00 135.00   0.50    0.20    --  107.11  19.00  60.00   54
 96  \w     35.00  78.00   0.50    0.20    --  107.11 -99.00 -60.00   86
 97  \w     35.00  60.00   0.50    0.20    --  107.11 -57.00 -90.00   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      -0.2402715000
_diffrn_orient_matrix_UB_12      0.1054064000
_diffrn_orient_matrix_UB_13      0.0191973000
_diffrn_orient_matrix_UB_21      -0.0203060000
_diffrn_orient_matrix_UB_22      -0.0227830000
_diffrn_orient_matrix_UB_23      0.1593447000
_diffrn_orient_matrix_UB_31      0.0814837000
_diffrn_orient_matrix_UB_32      0.1741924000
_diffrn_orient_matrix_UB_33      -0.0142668000
_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  0.0661
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11036
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.349
_diffrn_reflns_theta_min         4.625
_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    6.167
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.781
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_description       needle
_exptl_crystal_F_000             244
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0421P)^2^+0.8944P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1123
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1717
_reflns_number_total             1884
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt03260c1.cif
_cod_data_source_block           js1020v
_cod_depositor_comments
'Adding full bibliography for 7706457--7706460.cif.'
_cod_database_code               7706459
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C5H6N6O
_chemical_oxdiff_usercomment     YT7
_shelx_estimated_absorpt_t_max   0.887
_shelx_estimated_absorpt_t_min   0.413
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3A)
;
_shelx_res_checksum              36994
_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 YT7
_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 1.902
_oxdiff_exptl_absorpt_empirical_full_min 0.613