Chiral triptycene-pyrene π-conjugated chromophores with circularly polarized luminescence
Ikai, Tomoyuki; Wada, Yuya; Awata, Seiya; Yun, Changsik; Maeda, Katsuhiro; Mizuno, Motohiro; Swager, Timothy M.; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02046E

data_7155886
_publ_section_title
;
 Chiral triptycene-pyrene \p-conjugated chromophores with circularly
 polarized luminescence
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02046E
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C39.5 H25.65 Cl4.35 N2 O2'
_chemical_formula_weight         714.39
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-04-26 deposited with the CCDC.
2017-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.4015(3)
_cell_length_b                   12.4015(3)
_cell_length_c                   44.3208(11)
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.31
_cell_measurement_theta_min      3.70
_cell_volume                     6816.4(3)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            118581
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_min         3.564
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    3.715
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2932
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.988
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.09(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     956
_refine_ls_number_reflns         12478
_refine_ls_number_restraints     1127
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0723
_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^)+(0.0830P)^2^+16.9127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1932
_refine_ls_wR_factor_ref         0.1935
_reflns_Friedel_coverage         0.972
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                12367
_reflns_number_total             12478
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02046e2.cif
_cod_data_source_block           X17096
_cod_original_cell_volume        6816.4(4)
_cod_original_formula_sum        'C39.50 H25.65 Cl4.35 N2 O2'
_cod_database_code               7155886
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.392
_shelx_estimated_absorpt_t_max   0.794
_shelx_res_checksum              49358