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_4032710
_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_formula_moiety         'C34 H20 N4 O Pt, C H2 Cl2'
_chemical_formula_sum            'C35 H22 Cl2 N4 O Pt'
_chemical_formula_weight         780.55
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_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
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;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5292)
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_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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_temperature      190
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0710
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_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.757
_diffrn_reflns_theta_min         1.481
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_exptl_absorpt_coefficient_mu    4.945
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'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1069 before and 0.0557 after correction. The Ratio of minimum to maximum transmission is 0.7401. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            yellow
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_exptl_crystal_description       plate
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_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
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_refine_diff_density_min         -2.043
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0383P)^2^+0.0513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6032
_reflns_number_total             9188
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01568_si_003.cif
_cod_data_source_block           mo_dm17076_0m
_cod_database_code               4032710
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.908
_shelx_estimated_absorpt_t_min   0.638
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13),
 C14(H14), C20(H20), C21(H21), C25(H25), C26(H26), C27(H27), C28(H28), C31(H31),
  C32(H32), C33(H33), C34(H34)
;
_shelx_res_checksum              30445
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_olex2_submission_special_instructions 'No special instructions were received'