C-H Amination of Purine Derivatives via Radical Oxidative Coupling.
Luo, Zheng; Jiang, Ziyang; Jiang, Wei; Lin, Dongen; The Journal of organic chemistry 83 (2018) 3710–3718; doi:10.1021/acs.joc.8b00066

data_4035478
_publ_section_title
;
 C-H Amination of Purine Derivatives via Radical Oxidative Coupling.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3710
_journal_page_last               3718
_journal_paper_doi               10.1021/acs.joc.8b00066
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C13 H11 Cl N4 O'
_chemical_formula_sum            'C13 H11 Cl N4 O'
_chemical_formula_weight         274.71
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.108(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8846(3)
_cell_length_b                   11.6770(5)
_cell_length_c                   13.4919(6)
_cell_measurement_reflns_used    4236
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0740
_cell_measurement_theta_min      3.6730
_cell_volume                     1226.52(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.890
_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    -34.00  -2.00   1.00    1.27    --   11.74 -37.00  30.00   32
  2  \w    -62.00  99.00   1.00    1.27    --   11.74   0.00-120.00  161
  3  \w     15.00  40.00   1.00    1.27    --   11.74 -99.00-150.00   25
  4  \w    -17.00  31.00   1.00    1.27    --  -11.51-103.00-170.00   48
  5  \w     70.00  98.00   1.00    1.27    --   11.74-178.00-180.00   28
  6  \w    -49.00 -16.00   1.00    1.27    --  -11.51 103.00 -67.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0474052000
_diffrn_orient_matrix_UB_12      0.0392357000
_diffrn_orient_matrix_UB_13      -0.0249680000
_diffrn_orient_matrix_UB_21      -0.0180512000
_diffrn_orient_matrix_UB_22      -0.0331270000
_diffrn_orient_matrix_UB_23      -0.0444865000
_diffrn_orient_matrix_UB_31      -0.0757262000
_diffrn_orient_matrix_UB_32      0.0324343000
_diffrn_orient_matrix_UB_33      -0.0152205000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10364
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.462
_diffrn_reflns_theta_min         3.311
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0389P)^2^+0.3796P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2505
_reflns_number_total             3030
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00066_si_002.cif
_cod_data_source_block           exp_739
_cod_original_cell_volume        1226.50(9)
_cod_database_code               4035478
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.938
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C8(H8), C4(H4), C00G(H00G), C11(H11)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_olex2_date_sample_data_collection 2017-07-12
_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 1.427
_oxdiff_exptl_absorpt_empirical_full_min 0.601