CuCl-Catalyzed Hydroxylation of N-Heteroarylcarbazole Bromide: Approach for the Preparation of N-Heteroarylcarbazolyl Phenols and Its Application in the Synthesis of Phosphorescent Emitters.
Li, Guijie; Zhao, Xiangdong; Fang, Kun; Li, Jian; She, Yuanbin; The Journal of organic chemistry 82 (2017) 8634–8644; doi:10.1021/acs.joc.7b01568

data_4032683
_publ_section_title
;
 CuCl-Catalyzed Hydroxylation of N-Heteroarylcarbazole Bromide: Approach
 for the Preparation of N-Heteroarylcarbazolyl Phenols and Its Application
 in the Synthesis of Phosphorescent Emitters.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8634
_journal_page_last               8644
_journal_paper_doi               10.1021/acs.joc.7b01568
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C35 H22 Cl2 N4 O Pd'
_chemical_formula_weight         691.86
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                90
_cell_angle_beta                 103.209(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6518(12)
_cell_length_b                   10.0242(10)
_cell_length_c                   24.692(3)
_cell_measurement_reflns_used    5605
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.328
_cell_measurement_theta_min      4.403
_cell_volume                     2807.7(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
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_computing_structure_solution    'Bruker SHELXTL'
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_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
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_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16248
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         1.694
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
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_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
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_refine_diff_density_min         -0.521
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_refine_ls_abs_structure_details
; 
 Flack x determined using 3826 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.003(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         10196
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0605P)^2^+0.5629P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1075
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                9154
_reflns_number_total             10196
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           cd17063
_cod_depositor_comments          'Adding full bibliography for 4032683.cif.'
_cod_database_code               4032683
_shelx_estimated_absorpt_t_min   0.856
_shelx_estimated_absorpt_t_max   0.916
_shelxl_version_number           2013-4
_shelx_res_checksum              25985
_shelx_hkl_checksum              66885