BINOL derivatives with aggression-induced emission
Shi, Lei; Li, Kun; Cui, Peng-Cheng; Li, Ling-Ling; Pan, Sheng-Lin; Li, Meng-Yang; Yu, Xiao-Qi; Journal of Materials Chemistry B 6 (2018) 4413–; doi:10.1039/C8TB00774H

data_7237264
_publ_section_title
;
 BINOL derivatives with aggression-induced emission
;
_journal_issue                   27
_journal_name_full               'Journal of Materials Chemistry B'
_journal_page_first              4413
_journal_paper_doi               10.1039/C8TB00774H
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C32 H22 O8'
_chemical_formula_sum            'C32 H22 O8'
_chemical_formula_weight         534.49
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-04 deposited with the CCDC.
2018-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                71.882(7)
_cell_angle_beta                 78.624(5)
_cell_angle_gamma                75.444(6)
_cell_formula_units_Z            4
_cell_length_a                   12.7039(6)
_cell_length_b                   13.6838(11)
_cell_length_c                   20.0466(13)
_cell_measurement_reflns_used    6375
_cell_measurement_temperature    129.9(4)
_cell_measurement_theta_max      28.6370
_cell_measurement_theta_min      3.7260
_cell_volume                     3178.8(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      129.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -2.00   86.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419   38.0000  -30.0000 88

  2 omega   -4.00   82.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419    0.0000 -120.0000 86

  3 omega  -14.00   33.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419  -57.0000 -180.0000 47

  4 omega  -20.00   22.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -30.0000 42

  5 omega  -12.00   20.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000   90.0000 32

  6 omega  -49.00   34.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419  -57.0000   60.0000 83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0508084000
_diffrn_orient_matrix_UB_12      0.0249372000
_diffrn_orient_matrix_UB_13      -0.0131570000
_diffrn_orient_matrix_UB_21      -0.0037788000
_diffrn_orient_matrix_UB_22      0.0417321000
_diffrn_orient_matrix_UB_23      0.0148374000
_diffrn_orient_matrix_UB_31      0.0280792000
_diffrn_orient_matrix_UB_32      0.0272056000
_diffrn_orient_matrix_UB_33      -0.0318798000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25698
_diffrn_reflns_point_group_measured_fraction_full 0.706
_diffrn_reflns_point_group_measured_fraction_max 0.692
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.018
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2738 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1431
_refine_ls_number_reflns         17982
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0914P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1626
_reflns_Friedel_coverage         0.387
_reflns_Friedel_fraction_full    0.413
_reflns_Friedel_fraction_max     0.386
_reflns_number_gt                10819
_reflns_number_total             17982
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8tb00774h2.cif
_cod_data_source_block           171017_s5_sl
_cod_database_code               7237264
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.976
_reflns_odcompleteness_completeness 99.85
_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. Restrained distances
 C31C-C32C
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C32A) = Uanis(C32B) = Uanis(C32C) = Uanis(C32D)
4.a Secondary CH2 refined with riding coordinates:
 C15A(H15A,H15B), C31A(H31A,H31B), C15B(H15C,H15D), C31B(H31C,H31D), C15C(H15E,
 H15F), C31C(H31E,H31F), C15D(H15G,H15H), C31D(H31G,H31H)
4.b Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C7A(H7A), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), C21A(H21A),
 C23A(H23A), C25A(H25A), C26A(H26A), C27A(H27A), C28A(H28A), C5B(H5B), C7B(H7B),
  C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B), C21B(H21B), C23B(H23B),
 C25B(H25B), C26B(H26B), C27B(H27B), C28B(H28B), C5C(H5C), C7C(H7C), C9C(H9C),
 C10C(H10C), C11C(H11C), C12C(H12C), C21C(H21C), C23C(H23C), C25C(H25C),
 C26C(H26C), C27C(H27C), C28C(H28C), C5D(H5D), C7D(H7D), C9D(H9D), C10D(H10D),
 C11D(H11D), C12D(H12D), C21D(H21D), C23D(H23D), C25D(H25D), C26D(H26D),
 C27D(H27D), C28D(H28D)
4.c Idealised Me refined as rotating group:
 C16A(H16A,H16B,H16C), C32A(H32A,H32B,H32C), C16B(H16D,H16E,H16F), C32B(H32D,
 H32E,H32F), C16C(H16G,H16H,H16I), C32C(H32G,H32H,H32I), C16D(H16J,H16K,H16L),
 C32D(H32J,H32K,H32L)
;
_olex2_submission_special_instructions 'No special instructions were received'