Substitutent Effects in the Periphery of 2,9-Bisaryl-tetraazaperopyrene Dyes
Susanne C. Martens; Till Riehm; Sonja Geib; Hubert Wadepohl; Lutz H. Gade; Journal of Organic Chemistry 76 (2011) 609–617; doi:10.1021/jo102141w

data_4025996
_publ_section_title
;
 Substitutent Effects in the Periphery of 2,9-Bisaryl-tetraazaperopyrene
 Dyes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              609
_journal_page_last               617
_journal_paper_doi               10.1021/jo102141w
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C34 H8 Br2 F8 N4'
_chemical_formula_weight         784.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_sh3
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.334(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.7285(18)
_cell_length_b                   30.356(15)
_cell_length_c                   11.801(6)
_cell_measurement_reflns_used    6935
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.08
_cell_measurement_theta_min      2.65
_cell_volume                     1333.4(11)
_computing_cell_refinement
;
SAINT (Bruker AXS, 1997-2008). Includes estimated systematic errors
 of the unit cell constants from Monte Carlo simulations.
;
_computing_data_collection       'SMART-5.631 (Bruker AXS, 2003)'
_computing_data_reduction
'SAINT (Bruker AXS, 1997-2008); SADABS (Bruker AXS, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF (Beurskens et al., 1999-2008)'
_diffrn_ambient_environment      'perfluoro polyether oil'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.19
_diffrn_detector_type            CCD-PXL-KAF2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       '\f- and \w-scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            23953
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.85
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.133
_exptl_absorpt_correction_T_max  0.4296
_exptl_absorpt_correction_T_min  0.2256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements (Blessing 1995)
SADABS (Sheldrick & Bruker AXS, 2004-2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.953
_exptl_crystal_description       needle
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.757
_refine_diff_density_min         -1.119
_refine_diff_density_rms         0.158
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.227
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0895
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+15.6305P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2146
_refine_ls_wR_factor_ref         0.2190
_reflns_number_gt                2387
_reflns_number_total             2742
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102141w_si_002.cif
_cod_data_source_block           compound_7b
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4025996