Synthesis and Photophysical Properties of a 13,13'-Bibenzo[b]perylenyl Derivative as a π-Extended 1,1'-Binaphthyl Analog.
Uchida, Yosuke; Hirose, Takashi; Nakashima, Takuya; Kawai, Tsuyoshi; Matsuda, Kenji; Organic letters 18 (2016) 2118–2121; doi:10.1021/acs.orglett.6b00747

data_1543164
_publ_contact_author
;
Prof. Kenji Matsuda
Department of Synthetic Chemistry and Biological Chemistry,
Graduate School of Engineering,
Kyoto University, Katsura,
Nishikyo-ku, Kyoto 615-8510, Japan
;
_publ_section_title
;
 Synthesis and Photophysical Properties of a 13,13'-Bibenzo[b]perylenyl
 Derivative as a \p-Extended 1,1'-Binaphthyl Analog.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2118
_journal_page_last               2121
_journal_paper_doi               10.1021/acs.orglett.6b00747
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C64 H58, C7 H8'
_chemical_formula_sum            'C71 H66'
_chemical_formula_weight         919.23
_chemical_name_common            'compound 1'
_chemical_name_systematic
;
 2,2',13,13'-tetra-tert-butyl-11,11'-bibenzo[b]perylenyl
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                84.314(2)
_cell_angle_beta                 82.576(3)
_cell_angle_gamma                64.917(2)
_cell_formula_units_Z            2
_cell_length_a                   11.5438(12)
_cell_length_b                   13.2500(13)
_cell_length_c                   19.248(2)
_cell_measurement_reflns_used    14456
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      55.06
_cell_measurement_theta_min      6.07
_cell_volume                     2640.9(5)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID-S'
_diffrn_measurement_method       'phi and omega scans (omega-axis oscillation)'
_diffrn_radiation_monochromator  'flat graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25847
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.035
_diffrn_source                   'sealed Xray tube'
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
T. Higashi (March 2001). Program for Empirical Absorption Correction.
  Rigaku Corporation, Tokyo, Japan
;
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     746
_refine_ls_number_reflns         11998
_refine_ls_number_restraints     213
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0738
_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^)+(0.1440P)^2^+0.5344P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2229
_refine_ls_wR_factor_ref         0.2649
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7624
_reflns_number_total             11998
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00747_si_002.cif
_cod_data_source_block           b-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1543164.cif.
;
_cod_database_code               1543164
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              8261
_shelx_hkl_checksum              88929