Synthesis, Photophysical, and Electrochemical Properties of Pyrenes Substituted with Donors or Acceptors at the 4- or 4,9-Positions.
Ji, Lei; Krummenacher, Ivo; Friedrich, Alexandra; Lorbach, Andreas; Haehnel, Martin; Edkins, Katharina; Braunschweig, Holger; Marder, Todd B.; The Journal of organic chemistry 83 (2018) 3599–3606; doi:10.1021/acs.joc.7b03227

data_4035477
_publ_section_title
;
 Synthesis, Photophysical, and Electrochemical Properties of Pyrenes
 Substituted with Donors or Acceptors at the 4- or 4,9-Positions.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3599
_journal_page_last               3606
_journal_paper_doi               10.1021/acs.joc.7b03227
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C36 H48 B2 O4'
_chemical_formula_sum            'C36 H48 B2 O4'
_chemical_formula_weight         566.36
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-09-26
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.10(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.873(9)
_cell_length_b                   11.235(8)
_cell_length_c                   13.671(12)
_cell_measurement_reflns_used    7270
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.66
_cell_volume                     1612(2)
_computing_cell_refinement       'Saint+ ver. V8.30C (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.30C (Bruker AXS)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CMOS area detector (Photon 100)'
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20695
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.998
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.381
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9225
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'SadAbs 2012/1 (Bruker AXS)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_preparation       'cut and soaked in perfluoro polyether oil'
_exptl_crystal_recrystallization_method 'crystallised from DCM/hexanes'
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.348
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0662P)^2^+0.6915P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2717
_reflns_number_total             3167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03227_si_005.cif
_cod_data_source_block           13S081
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035477
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              13008
_shelx_hkl_checksum              6298