Bridged o-carborane–anthracene dyads as dual state emission luminogens: synthesis, characterization, and mechanochromic properties
Xu, Chunyue; Li, Tianrui; Miao, Jinling; Liu, Kexin; Nie, Yong; Liu, Guangning; Jiang, Xuchuan; New Journal of Chemistry 47 (2023) 4448–4456; doi:10.1039/D3NJ00027C

data_7062237
_publ_section_title
;
 Bridged o-carborane--anthracene dyads as dual state emission luminogens:
 synthesis, characterization, and mechanochromic properties
;
_journal_issue                   9
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4448
_journal_page_last               4456
_journal_paper_doi               10.1039/D3NJ00027C
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C17 H23 B10 N'
_chemical_formula_sum            'C17 H23 B10 N'
_chemical_formula_weight         349.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-21 deposited with the CCDC.	2023-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   24.8057(6)
_cell_length_b                   15.1639(4)
_cell_length_c                   21.0939(6)
_cell_measurement_reflns_used    11784
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0600
_cell_measurement_theta_min      3.5000
_cell_volume                     7934.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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_detector_area_resol_mean 16.0355
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -51.00  43.00   1.00  132.74    --   16.33 -77.00  90.00   94
  2  \w    -10.00  84.00   1.00  132.74    --   16.33  77.00-150.00   94
  3  \w    -51.00  33.00   1.00  132.74    --   16.33 -57.00 -30.00   84
  4  \w    -25.00  22.00   1.00  132.74    --  -16.64 -99.00   0.00   47
  5  \w    -25.00  22.00   1.00  132.74    --  -16.64 -99.00-120.00   47
  6  \w      0.00  84.00   1.00  132.74    --   16.33  57.00 120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0257418000
_diffrn_orient_matrix_UB_12      0.0142121000
_diffrn_orient_matrix_UB_13      0.0050432000
_diffrn_orient_matrix_UB_21      0.0116854000
_diffrn_orient_matrix_UB_22      0.0303747000
_diffrn_orient_matrix_UB_23      -0.0060631000
_diffrn_orient_matrix_UB_31      -0.0043611000
_diffrn_orient_matrix_UB_32      -0.0024419000
_diffrn_orient_matrix_UB_33      -0.0460921000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            65154
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         3.294
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       plate
_exptl_crystal_F_000             2912
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 3151 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1009
_refine_ls_number_reflns         14730
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0686
_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^)+(0.0749P)^2^+3.4608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.1947
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                9314
_reflns_number_total             14730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj00027c2.cif
_cod_data_source_block           20211117_ny_xcy45
_cod_depositor_comments
;
          Adding full bibliography for 7062237.cif.

2024-09-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C68 H92 B40 N4'
_cod_original_formula_weight         1397.85
_cod_original_formula_moiety         '4(C17 H23 B10 N)'
_cod_original_formula_units_Z            4
_cod_database_code               7062237
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N B'
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.962
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 N1(H1), N2(H2A), N3(H3C)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C20(H20A,H20B), C37(H37A,H37B), C54(H54A,H54B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C30(H30), C31(H31),
  C32(H32), C33(H33), C40(H40), C41(H41), C42(H42), C43(H43), C45(H45),
 C47(H47), C48(H48), C49(H49), C50(H50), N4(H4A), C57(H57), C58(H58), C59(H59),
 C60(H60), C62(H62), C64(H64), C65(H65), C66(H66), C67(H67)
2.d Boron cage BH refined with riding coordinates:
 C1(H1A), B1(H1B), B2(H2), B3(H3), B4(H4), B5(H5), B6(H6A), B7(H7A), B8(H8A),
 B9(H9A), B10(H10), C18(H18), B11(H11A), B12(H12), B13(H13A), B14(H14A),
 B15(H15A), B16(H16A), B17(H17), B18(H18A), B19(H19), B20(H20), C35(H35),
 B21(H21), B22(H22), B23(H23A), B24(H24A), B25(H25A), B26(H26A), B27(H27),
 B28(H28A), B29(H29), B30(H30A), C52(H52), B31(H31A), B32(H32A), B33(H33A),
 B34(H34), B35(H35A), B36(H36), B37(H37), B38(H38), B39(H39), B40(H40A)
;
_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 1.212
_oxdiff_exptl_absorpt_empirical_full_min 0.765