Cobalt(iii)-catalyzed C-H halogenation of 6-arylpurines: facile entry into arylated, sulfenylated and alkoxylated 6-arylpurines.
Pawar, Amit B.; Lade, Dhanaji M.; Organic & biomolecular chemistry 14 (2016) 3275–3283; doi:10.1039/c5ob02640g

data_7154993
_publ_section_title
;
 Cobalt(iii)-catalyzed C-H halogenation of 6-arylpurines: facile entry
 into arylated, sulfenylated and alkoxylated 6-arylpurines.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3275
_journal_page_last               3283
_journal_paper_doi               10.1039/c5ob02640g
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C15 H15 I N4'
_chemical_formula_sum            'C15 H15 I N4'
_chemical_formula_weight         378.21
_chemical_name_systematic        amit
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-11-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-11-05 deposited with the CCDC.
2016-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.417(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5445(7)
_cell_length_b                   14.1434(15)
_cell_length_c                   14.8389(15)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    298
_cell_volume                     1557.3(3)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22538
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.005
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.052
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0728 before and 0.0413 after correction.
The Ratio of minimum to maximum transmission is 0.8020.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.899
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0435P)^2^+2.5208P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2536
_reflns_number_total             2739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02640g2.cif
_cod_data_source_block           red
_cod_depositor_comments          'Adding full bibliography for 7154993.cif.'
_cod_database_code               7154993
_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:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              3329
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id Amit
_olex2_submission_special_instructions 'No special instructions were received'