1,1′-Bi(2-naphthol-4,5-dicarboximide)s: blue emissive axially chiral scaffolds with aggregation-enhanced emission properties
Chen, Meng-Ting; Zhang, Yang; Vysotsky, Myroslav O.; Lindner, Joachim O.; Li, Meng-Hua; Lin, Mei-Jin; Würthner, Frank; Organic Chemistry Frontiers 6 (2019) 3731–; doi:10.1039/C9QO01090D

data_1555178
_publ_section_title
;
 1,1&#x2032;-Bi(2-naphthol-4,5-dicarboximide)s: blue emissive axially
 chiral scaffolds with aggregation-enhanced emission properties
;
_journal_issue                   22
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3731
_journal_paper_doi               10.1039/C9QO01090D
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C34 H26.08 N2 O6'
_chemical_formula_sum            'C34 H27.62 N2 O6'
_chemical_formula_weight         560.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-07-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-06 deposited with the CCDC.	2019-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                113.157(7)
_cell_angle_beta                 97.019(6)
_cell_angle_gamma                110.996(6)
_cell_formula_units_Z            2
_cell_length_a                   10.4723(7)
_cell_length_b                   12.7127(9)
_cell_length_c                   12.7391(9)
_cell_measurement_reflns_used    4441
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5100
_cell_measurement_theta_min      2.8240
_cell_volume                     1385.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.817
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -79.00 -53.00   0.50    9.00    --    5.00  29.00-180.00   52
  2  \w    -27.00  -1.00   0.50    9.00    --    5.00  29.00-180.00   52
  3  \w    -84.00 -58.00   0.50    9.00    --   -7.70  55.00-180.00   52
  4  \w     -7.00  81.00   0.50    9.00    --   -7.70  55.00 -60.00  176
  5  \w    -80.00 -52.00   0.50    9.00    --   -7.70  55.00  60.00   56
  6  \w    -18.00  74.00   0.50    9.00    --   -7.70  55.00  60.00  184
  7  \w    -28.00  80.00   0.50    9.00    --   -7.70  55.00-180.00  216
  8  \w    -28.00  73.00   0.50    9.00    --   -7.70  29.00  60.00  202
  9  \w    -77.00 -51.00   0.50    9.00    --   -7.70  29.00  60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0041659000
_diffrn_orient_matrix_UB_12      0.0454768000
_diffrn_orient_matrix_UB_13      0.0566549000
_diffrn_orient_matrix_UB_21      -0.0601067000
_diffrn_orient_matrix_UB_22      -0.0476071000
_diffrn_orient_matrix_UB_23      0.0016411000
_diffrn_orient_matrix_UB_31      0.0466771000
_diffrn_orient_matrix_UB_32      -0.0160845000
_diffrn_orient_matrix_UB_33      0.0288957000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.817
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20408
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.792
_diffrn_reflns_theta_min         1.827
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       needle
_exptl_crystal_F_000             587
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.022
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         6490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0784
_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^)+(0.1682P)^2^+0.3288P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2369
_refine_ls_wR_factor_ref         0.2764
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4057
_reflns_number_total             6490
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo01090d2.cif
_cod_data_source_block           8a
_cod_original_cell_volume        1385.74(19)
_cod_database_code               1555178
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H01H)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=Sof(H5A)=Sof(C2A)=Sof(H2A)=1-
 FVAR(1)
 Sof(H013)=Sof(C4)=Sof(C2)=Sof(C5)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C00Z(H00H,H00I), C010(H01A,H01B), C011(H01C,H01D), C4A(H4AA,H4AB)
3.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00J(H00J), C00K(H00K), C00M(H00M), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00V(H00V), C5A(H5A)
3.c Idealised Me refined as rotating group:
 C00X(H00A,H00B,H00C), C00Y(H00D,H00E,H00F), C012(H01E,H01F,H01G)
3.d :
 C2A(H2A)
;
_shelx_res_checksum              32125
_shelx_hkl_checksum              41879
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.335
_oxdiff_exptl_absorpt_empirical_full_min 0.452