Concentration-dependent circularly polarized luminescence (CPL) of chiral N,N’-dipyrenyldiamines: sign-inverted CPL switching between the monomer and excimer region under retention of the monomer emission for the photoluminescence
Ito, Suguru; Ikeda, Kengo; Nakanishi, Shoma; Imai, Yoshitane; Asami, Masatoshi; Chem. Commun.  (2017) –; doi:10.1039/C7CC01351E

data_7120068
_publ_section_title
;
 Concentration-dependent circularly polarized luminescence (CPL) of chiral
 N,N&#x2019;-dipyrenyldiamines: sign-inverted CPL switching between the
 monomer and excimer region under retention of the monomer emission for
 the photoluminescence
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC01351E
_journal_year                    2017
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C50 H38 N2 O'
_chemical_formula_sum            'C50 H38 N2 O'
_chemical_formula_weight         682.86
_chemical_melting_point          509.9(5)
_chemical_name_systematic
(S,S)-4,6-Bis(1-(pyren-1-ylamino)propyl)dibenzo[b,d]furan
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2017-02-06 deposited with the CCDC.
2017-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   10.136(3)
_cell_length_b                   11.918(4)
_cell_length_c                   29.359(8)
_cell_measurement_reflns_used    5317
_cell_measurement_temperature    223
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      1.71
_cell_volume                     3546.6(19)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            28325
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         3.260
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1440.00
_exptl_crystal_preparation       ', Luminescent'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/diethyl ether'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.19
_refine_ls_abs_structure_details
;
 Flack x determined using 910 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     486
_refine_ls_number_reflns         8126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1874
_refine_ls_R_factor_gt           0.1004
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0521P)^2^+0.8377P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1714
_refine_ls_wR_factor_ref         0.2128
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4068
_reflns_number_total             8126
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c7cc01351e2.cif
_cod_data_source_block           ike401
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '509.45-510.45' was changed to
'509.9(5)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        3546.4(18)
_cod_database_code               7120068
_shelx_res_checksum              64598