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_4035476
_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, 0.5(C2 H3 N)'
_chemical_formula_sum            'C37 H49.5 B2 N0.5 O4'
_chemical_formula_weight         586.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-12-19
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.598(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   40.616(11)
_cell_length_b                   9.877(3)
_cell_length_c                   17.437(5)
_cell_measurement_reflns_used    3485
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.80
_cell_measurement_theta_min      2.40
_cell_volume                     6973(3)
_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (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                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30481
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.012
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9986
_exptl_absorpt_correction_T_min  0.9497
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'SadAbs 2012/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_description       block
_exptl_crystal_F_000             2536
_exptl_crystal_size_max          0.464
_exptl_crystal_size_mid          0.363
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         6154
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1444
_refine_ls_R_factor_gt           0.0785
_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^)+(0.1217P)^2^+7.9136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2060
_refine_ls_wR_factor_ref         0.2475
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3393
_reflns_number_total             6154
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03227_si_006.cif
_cod_data_source_block           cmpd_7
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C37 H49.50 B2 N0.50 O4'
_cod_database_code               4035476
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              88349
_shelx_hkl_checksum              76666