Copper-Catalyzed 8-Aminoquinoline-Directed Selenylation of Arene and Heteroarene C-H Bonds.
Mandal, Anup; Sahoo, Harekrishna; Baidya, Mahiuddin; Organic letters 18 (2016) 3202–3205; doi:10.1021/acs.orglett.6b01420

data_1543794
_publ_section_title
;
 Copper-Catalyzed 8-Aminoquinoline-Directed Selenylation of Arene and
 Heteroarene C-H Bonds.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3202
_journal_page_last               3205
_journal_paper_doi               10.1021/acs.orglett.6b01420
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C27 H17 Cl2 N3 O Se2, H2 O  '
_chemical_formula_sum            'C27 H19 Cl2 N3 O2 Se2'
_chemical_formula_weight         646.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
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_cell_angle_beta                 85.1858(16)
_cell_angle_gamma                88.7061(17)
_cell_formula_units_Z            2
_cell_length_a                   7.5562(3)
_cell_length_b                   13.4128(7)
_cell_length_c                   14.1944(7)
_cell_measurement_reflns_used    5953
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.34
_cell_measurement_theta_min      2.71
_cell_volume                     1297.21(11)
_computing_cell_refinement       'Bruker SAINT'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
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_diffrn_reflns_limit_k_max       15
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_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17540
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.591
_exptl_absorpt_coefficient_mu    3.087
_exptl_absorpt_correction_T_max  0.577
_exptl_absorpt_correction_T_min  0.458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4551
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0542P)^2^+0.6044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3565
_reflns_number_total             4551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01420_si_004.cif
_cod_data_source_block           188
_cod_database_code               1543794
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.458
_shelx_estimated_absorpt_t_max   0.577
_shelx_res_checksum              12865
_shelx_hkl_checksum              69268