A cross-coupling-annulation cascade from peri-dibromonaphthalimide to pseudo-rylene bisimides
Seifert, Sabine; Schmidt, David; Würthner, Frank; Organic Chemistry Frontiers 3 (2016) 1435–; doi:10.1039/C6QO00421K

data_1553513
_publ_section_title
;
 A cross-coupling-annulation cascade from peri-dibromonaphthalimide to
 pseudo-rylene bisimides
;
_journal_issue                   11
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1435
_journal_paper_doi               10.1039/C6QO00421K
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C64 H48 N2 O4, 2 (C7 H8), C H2 Cl2'
_chemical_formula_sum            'C79 H66 Cl2 N2 O4'
_chemical_formula_weight         1178.23
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-08-01 deposited with the CCDC.
2016-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.839(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.3641(12)
_cell_length_b                   15.7960(14)
_cell_length_c                   14.8901(13)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      2.58
_cell_volume                     2896.9(4)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            48026
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.145
_diffrn_reflns_theta_min         1.653
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7068
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'Sadabs 2008/1 (Bruker 2008)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         5776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0708P)^2^+2.2292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1459
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4550
_reflns_number_total             5776
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00421k2.cif
_cod_data_source_block           DS_SS189_fertig
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1553513
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              40888
_shelx_hkl_checksum              91592