Metal-free Annulation at the Ortho- and Bay-Positions of Perylene Bisimide Leading to Lateral π-Extension with Strong NIR Absorption.
Regar, Ramprasad; Mishra, Ruchika; Mondal, Pradip Kumar; Sankar, Jeyaraman; The Journal of organic chemistry 83 (2018) 9547–9552; doi:10.1021/acs.joc.8b01303

data_4035304
_publ_section_title
;
 Metal-free Annulation at the Ortho- and Bay-Positions of Perylene
 Bisimide Leading to Lateral \p-Extension with Strong NIR Absorption.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9547
_journal_page_last               9552
_journal_paper_doi               10.1021/acs.joc.8b01303
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C23 H22 Cl6 N2 O3'
_chemical_formula_weight         587.12
_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-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 98.83(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.463(4)
_cell_length_b                   25.511(11)
_cell_length_c                   15.188(8)
_cell_measurement_reflns_used    1135
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      16.68
_cell_measurement_theta_min      2.71
_cell_volume                     2474(2)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.2564
_diffrn_reflns_av_unetI/netI     0.3454
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6843
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        23.405
_diffrn_reflns_theta_max         23.405
_diffrn_reflns_theta_min         2.095
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  0.8460
_exptl_absorpt_correction_T_min  0.6432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/4'
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.2700
_refine_ls_R_factor_gt           0.0997
_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^)+(0.0565P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1999
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1392
_reflns_number_total             3578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01303_si_003.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        2475(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035304
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.918
_shelx_estimated_absorpt_t_max   0.958
_shelx_res_checksum              51709
_shelx_hkl_checksum              52883