Synthesis of Octabromoperylene Dianhydride and Diimides: Evidence of Halogen Bonding and Semiconducting Properties.
Kumar, Yogendra; Kumar, Sharvan; Kumar Keshri, Sudhir; Shukla, Jyoti; Singh, Shiv Shankar; Thakur, Tejender S.; Denti, Mitchell; Facchetti, Antonio; Mukhopadhyay, Pritam; Organic letters 18 (2016) 472–475; doi:10.1021/acs.orglett.5b03513

data_1542688
_publ_section_title
;
 Synthesis of Octabromoperylene Dianhydride and Diimides: Evidence of
 Halogen Bonding and Semiconducting Properties.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              472
_journal_page_last               475
_journal_paper_doi               10.1021/acs.orglett.5b03513
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C24 Br8 O6, 2(C4 H8 O)'
_chemical_formula_sum            'C32 H16 Br8 O8'
_chemical_formula_weight         1167.73
_chemical_name_common            'Octa-bromo Perylenecarboxylicdianhydride'
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 128.249(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.0972(18)
_cell_length_b                   15.0686(13)
_cell_length_c                   14.2085(12)
_cell_measurement_reflns_used    5431
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      25.18
_cell_measurement_theta_min      2.46
_cell_volume                     3547.3(5)
_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    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17752
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.194
_diffrn_reflns_theta_min         2.459
_exptl_absorpt_coefficient_mu    9.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.187
_exptl_crystal_description       'rectangular - block'
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   0.635
_exptl_transmission_factor_min   0.422
_platon_squeeze_details
;
 ?
;
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.4423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1350
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2245
_reflns_number_total             3174
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03513_si_002.cif
_cod_data_source_block           YK4_0m_a
_cod_database_code               1542688
_shelx_estimated_absorpt_t_min   0.342
_shelx_estimated_absorpt_t_max   0.659
_shelxl_version_number           2014-3
_shelx_res_checksum              28525
_shelx_hkl_checksum              39995