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_7706460
_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         'Cl, C4 H6 N7 O, 2(H2 O)'
_chemical_formula_sum            'C4 H10 Cl N7 O3'
_chemical_formula_weight         239.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-02
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.10.28 svn.r5b043f8a for OlexSys, GUI svn.r6176)
;
_audit_update_record
;
2020-11-03 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.961(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3157(4)
_cell_length_b                   9.2267(4)
_cell_length_c                   12.9583(6)
_cell_measurement_reflns_used    4640
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9140
_cell_measurement_theta_min      5.8740
_cell_volume                     988.87(8)
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_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     50.00  75.00   0.50    0.05    --   47.45  68.00 115.00   50
  2  \w     89.00 130.00   0.50    0.16    --  107.11  68.00 115.00   82
  3  \w    137.00 174.00   0.50    0.16    --  107.11  57.00 150.00   74
  4  \w    137.00 170.00   0.50    0.16    --  107.11  68.00 115.00   66
  5  \w    128.00 158.00   0.50    0.16    --  107.11  57.00 -30.00   60
  6  \w    140.00 168.00   0.50    0.16    --  107.11  57.00-150.00   56
  7  \w    142.00 168.00   0.50    0.16    --  107.11  37.00-120.00   52
  8  \w    114.00 141.00   0.50    0.16    --  107.11  37.00-120.00   54
  9  \w     95.00 139.00   0.50    0.16    --  107.11  19.00-150.00   88
 10  \w    117.00 147.00   0.50    0.16    --  107.11  37.00-150.00   60
 11  \w     95.00 135.00   0.50    0.16    --  107.11  19.00 -60.00   80
 12  \w    114.00 178.00   0.50    0.16    --  107.11  37.00   0.00  128
 13  \w    123.00 178.00   0.50    0.16    --  107.11  37.00  30.00  110
 14  \w     97.00 174.00   0.50    0.16    --  107.11  19.00  90.00  154
 15  \w    -41.00 -16.00   0.50    0.16    --  -86.25  37.00 -60.00   50
 16  \w    -56.00 -30.00   0.50    0.05    --  -47.45 125.00-150.00   52
 17  \w    -79.00 -18.00   0.50    0.16    --  -86.25  68.00 115.00  122
 18  \w   -157.00-132.00   0.50    0.16    --  -86.25 -77.00 -60.00   50
 19  \w   -156.00-130.00   0.50    0.16    --  -86.25 -37.00 -60.00   52
 20  \w   -119.00 -88.00   0.50    0.16    --  -86.25 -30.00-148.73   62
 21  \w   -112.00 -28.00   0.50    0.05    --  -47.45 -68.00 -18.00  168
 22  \w   -117.00 -84.00   0.50    0.16    --  -86.25 -29.00-171.90   66
 23  \w   -131.00 -90.00   0.50    0.16    --  -86.25 -68.00 -18.00   82
 24  \w   -109.00 -80.00   0.50    0.16    --  -86.25 -29.00 169.72   58
 25  \w   -155.00 -75.00   0.50    0.16    --  -86.25 -26.00 137.18  160
 26  \w   -141.00-116.00   0.50    0.16    --  -86.25 -29.00 169.72   50
 27  \w   -159.00-133.00   0.50    0.16    --  -86.25 -77.00 120.00   52
 28  \w   -105.00 -77.00   0.50    0.16    --  -86.25 -24.00-141.79   56
 29  \w    -27.00  26.00   0.50    0.05    --  -47.45  19.00 120.00  106
 30  \w    -14.00  16.00   0.50    0.05    --  -47.45  68.00 115.00   60
 31  \w    -64.00 -26.00   0.50    0.05    --  -47.45  68.00 115.00   76
 32  \w    -61.00  15.00   0.50    0.05    --  -47.45  57.00 -30.00  152
 33  \w     52.00  95.00   0.50    0.16    --  107.11 -99.00  60.00   86
 34  \w     35.00  63.00   0.50    0.16    --  107.11 -57.00  30.00   56
 35  \w     39.00  96.00   0.50    0.16    --  107.11 -77.00 -30.00  114
 36  \w     69.00  95.00   0.50    0.16    --  107.11 -77.00  30.00   52
 37  \w     43.00  76.00   0.50    0.16    --  107.11 -68.00 -18.00   66
 38  \w     35.00  60.00   0.50    0.16    --  107.11 -57.00 120.00   50
 39  \w     38.00  63.00   0.50    0.16    --  107.11 -57.00 150.00   50
 40  \w     38.00  63.00   0.50    0.16    --  107.11 -57.00   0.00   50
 41  \w     14.00  39.00   0.50    0.05    --   47.45 -68.00 -18.00   50
 42  \w     36.00  65.00   0.50    0.16    --  107.11 -57.00-150.00   58
 43  \w     35.00  60.00   0.50    0.16    --  107.11 -57.00-180.00   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      0.0976490000
_diffrn_orient_matrix_UB_12      -0.0850789000
_diffrn_orient_matrix_UB_13      -0.0743834000
_diffrn_orient_matrix_UB_21      -0.1479510000
_diffrn_orient_matrix_UB_22      -0.0973138000
_diffrn_orient_matrix_UB_23      -0.0306276000
_diffrn_orient_matrix_UB_31      -0.0567468000
_diffrn_orient_matrix_UB_32      0.1057762000
_diffrn_orient_matrix_UB_33      -0.0884595000
_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  0.0557
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11264
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.347
_diffrn_reflns_theta_min         5.898
_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    3.531
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.579
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0625P)^2^+0.6790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1862
_reflns_number_total             2044
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt03260c1.cif
_cod_data_source_block           js920f_y
_cod_depositor_comments
'Adding full bibliography for 7706457--7706460.cif.'
_cod_original_cell_volume        988.87(7)
_cod_database_code               7706460
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C4H5N7O
_chemical_oxdiff_usercomment     'YT5 '
_shelx_estimated_absorpt_t_max   0.835
_shelx_estimated_absorpt_t_min   0.519
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_res_checksum              67626
_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 YT-5
_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 1.760
_oxdiff_exptl_absorpt_empirical_full_min 0.710