Ir-Catalyzed Direct Borylation at the 4-Position of Pyrene
Zhiqiang Liu; Yuanyuan Wang; Ying Chen; Jie Liu; Qi Fang; Christian Kleeberg; Todd B. Marder; Journal of Organic Chemistry 77 (2012) 7124–7128; doi:10.1021/jo301293w

data_4027410
_publ_section_title
;
 Ir-Catalyzed Direct Borylation at the 4-Position of Pyrene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7124
_journal_page_last               7128
_journal_paper_doi               10.1021/jo301293w
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C37 H28'
_chemical_formula_sum            'C37 H28'
_chemical_formula_weight         472.59
_chemical_melting_point          475
_chemical_name_common            2,4,7-tri-tolyl-pyrene
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.458(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.459(5)
_cell_length_b                   15.980(12)
_cell_length_c                   24.291(19)
_cell_measurement_reflns_used    2566
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.03
_cell_measurement_theta_min      2.55
_cell_volume                     2496(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            26001
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_correction_T_min  0.9660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker,2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       needle
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0033(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0798P)^2^+0.5554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1912
_reflns_number_gt                2425
_reflns_number_total             4890
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301293w_si_004.cif
_cod_data_source_block           liuzq20110621_0m
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4027410