Selective Bromination of Perylene Diimides under Mild Conditions
Paramasivan Rajasingh; Revital Cohen; Elijah Shirman; Linda J. W. Shimon; Boris Rybtchinski; Journal of Organic Chemistry 72 (2007) 5973–5979; doi:10.1021/jo070367n

data_4024083
_publ_section_title
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 Selective Bromination of Perylene Diimides under Mild Conditions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5973
_journal_page_last               5979
_journal_paper_doi               10.1021/jo070367n
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C37 H35 Br2 N2 O4'
_chemical_formula_weight         731.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.2930(10)
_cell_angle_beta                 68.7930(13)
_cell_angle_gamma                89.1380(13)
_cell_formula_units_Z            2
_cell_length_a                   10.5940(2)
_cell_length_b                   11.2600(3)
_cell_length_c                   14.3580(3)
_cell_measurement_reflns_used    6864
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.55
_cell_volume                     1571.93(6)
_computing_cell_refinement       HKL
_computing_data_collection       'Collect package (BrukerNonius)'
_computing_data_reduction        HKL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5750
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    2.623
_exptl_absorpt_correction_T_max  0.7794
_exptl_absorpt_correction_T_min  0.6220
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             746
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.821
_refine_diff_density_min         -0.814
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0831P)^2^+3.0197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1477
_reflns_number_gt                4888
_reflns_number_total             5750
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070367nsi20070222_010107.cif
_cod_data_source_block           r11na
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_database_code               4024083