Extension of Pyrrolopyrrole π-System: Approach to Constructing Hexacyclic Nitrogen-Containing Aromatic Systems.
Tasior, Mariusz; Chotkowski, Maciej; Gryko, Daniel T.; Organic letters 17 (2015) 6106–6109; doi:10.1021/acs.orglett.5b03129

data_1555458
_publ_section_title
;
 Extension of Pyrrolopyrrole \p-System: Approach to Constructing
 Hexacyclic Nitrogen-Containing Aromatic Systems.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6106
_journal_page_last               6109
_journal_paper_doi               10.1021/acs.orglett.5b03129
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C56 H40 F6 N6'
_chemical_formula_sum            'C56 H40 F6 N6'
_chemical_formula_weight         910.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 94.823(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.398(2)
_cell_length_b                   11.831(3)
_cell_length_c                   25.874(7)
_cell_measurement_reflns_used    2980
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.55
_cell_measurement_theta_min      3.43
_cell_volume                     2256.6(10)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            32435
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.550
_diffrn_reflns_theta_min         3.428
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_T_max  0.8830
_exptl_absorpt_correction_T_min  0.8090
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisms
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0639
_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^)+(0.0795P)^2^+1.5688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2980
_reflns_number_total             4116
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03129_si_002.cif
_cod_data_source_block           MT843_0m
_cod_original_cell_volume        2256.6(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1555458
_shelx_estimated_absorpt_t_min   0.809
_shelx_estimated_absorpt_t_max   0.883
_shelxl_version_number           2014-3
_shelx_res_checksum              29064
_shelx_hkl_checksum              71801