Synthesis, Optical, and Redox Properties of Regioisomeric Benzoheterocycles-Fused Pyrene.
Mocanu, Anabella; Szűcs, Rózsa; Caytan, Elsa; Roisnel, Thierry; Dorcet, Vincent; Bouit, Pierre-Antoine; Nyulászi, László; Hissler, Muriel; The Journal of organic chemistry 84 (2019) 957–962; doi:10.1021/acs.joc.8b02884

data_4035955
_publ_section_title
;
 Synthesis, Optical, and Redox Properties of Regioisomeric
 Benzoheterocycles-Fused Pyrene.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              957
_journal_page_last               962
_journal_paper_doi               10.1021/acs.joc.8b02884
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C24 H18 Si'
_chemical_formula_sum            'C24 H18 Si'
_chemical_formula_weight         334.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0297(3)
_cell_length_b                   10.1542(3)
_cell_length_c                   19.3621(6)
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.26
_cell_measurement_wavelength     0.71073
_cell_volume                     1775.30(10)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            27809
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         3.019
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.350
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
Flack x determined using 1623 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_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     228
_refine_ls_number_reflns         4086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0484P)^2^+0.3190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3883
_reflns_number_total             4086
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02884_si_002.cif
_cod_data_source_block           JOB
_cod_database_code               4035955
_shelx_res_checksum              32252
_shelx_hkl_checksum              69857