An o-carborane-based naphthalene macrocyclic arene: dual-state emission and C60 recognition
Chen, Wenlong; Yuan, Shuai; Lin, Caixia; Yuan, Yaofeng; New Journal of Chemistry  (2026) –; doi:10.1039/D6NJ00521G

data_7064373
_publ_section_title
;
 An o-carborane-based naphthalene macrocyclic arene: dual-state emission
 and C60 recognition
;
_journal_issue                   16
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6989
_journal_page_last               6995
_journal_paper_doi               10.1039/D6NJ00521G
_journal_volume                  50
_journal_year                    2026
_chemical_formula_moiety         '2(C25 H28 B10 O2)'
_chemical_formula_sum            'C50 H56 B20 O4'
_chemical_formula_weight         937.14
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2026-02-07 deposited with the CCDC.	2026-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                91.335(3)
_cell_angle_beta                 99.372(3)
_cell_angle_gamma                118.660(6)
_cell_formula_units_Z            2
_cell_length_a                   11.3775(6)
_cell_length_b                   11.5862(7)
_cell_length_c                   25.9327(6)
_cell_measurement_reflns_used    11465
_cell_measurement_temperature    296.15(10)
_cell_measurement_theta_max      77.1710
_cell_measurement_theta_min      4.4330
_cell_volume                     2939.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.124a (Rigaku OD, 2024)'
_computing_data_collection
'PROGRAM:BIS 8.5.0.27 Release/2023-03-20 && APEX5 2023.9-2                       '
_computing_data_reduction        'CrysAlisPro 1.171.43.124a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.15(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    -25.75 154.25   1.00    1.00 -25.75 -55.00  73.76    --   180
  2  \f    154.25 334.25   1.00    1.00 -25.75 -55.00  73.76    --   180
  3  \f    154.25 334.25   1.00    1.00 -25.75 -55.00  73.76    --   180
  4  \f    -25.75 154.25   1.00    1.00 -25.75 -55.00  73.76    --   180
  5  \f     -9.39 350.61   0.50    1.00 -19.26-110.12  28.85    --   720
  6  \f   -339.92  20.08   0.50    1.00 -54.46 -80.12 -59.25    --   720
  7  \w   -138.60 -22.10   0.50    1.00    -- -110.12  88.31-135.97  233
  8  \w   -138.60 -22.10   0.50    1.00    -- -110.12  88.31  32.03  233
  9  \w    -21.13  86.87   0.50    1.00    --   45.19 -88.31  31.97  216
 10  \w    -21.13  86.87   0.50    1.00    --   45.19 -88.31-128.03  216
 11  \w      4.61 112.61   0.50    1.00    --   30.19  59.25 -20.08  216
 12  \w      4.61 112.61   0.50    1.00    --   30.19  59.25 159.92  216
 13  \f   -350.61   9.39   0.50    1.00 -93.29-110.12 -28.85    --   720
 14  \w   -138.60 -22.10   0.50    1.00    -- -110.12  88.31 160.03  233
 15  \w      4.61 112.61   0.50    1.00    --   30.19  59.25  69.92  216
 16  \w   -138.60 -22.10   0.50    1.00    -- -110.12  88.31  96.03  233
 17  \f   -339.92  20.08   0.50    1.00 -69.46 -95.12 -59.25    --   720
 18  \w   -138.60 -22.10   0.50    1.00    -- -110.12  88.31 -71.97  233
 19  \w      4.61 112.61   0.50    1.00    --   30.19  59.25-110.08  216
 20  \w    206.07 290.57   0.50    1.00    --  -95.12 -59.25-159.92  169
 21  \w    -21.13  86.87   0.50    1.00    --   45.19 -88.31 111.97  216
 22  \w   -138.60 -22.10   0.50    1.00    -- -110.12  88.31 -31.97  233
 23  \w    206.07 305.57   0.50    1.00    --  -80.12 -59.25  20.08  199
 24  \w    206.07 290.57   0.50    1.00    --  -95.12 -59.25 -69.92  169
 25  \w    206.07 305.57   0.50    1.00    --  -80.12 -59.25 110.08  199
 26  \w   -138.60 -22.10   0.50    1.00    -- -110.12  88.31  64.03  233
 27  \w   -138.60 -22.10   0.50    1.00    -- -110.12  88.31-167.97  233
 28  \w   -138.60 -22.10   0.50    1.00    -- -110.12  88.31 128.03  233
 29  \w   -138.60 -22.10   0.50    1.00    -- -110.12  88.31   0.03  233
 30  \w    206.07 305.57   0.50    1.00    --  -80.12 -59.25 -69.92  199
 31  \w   -138.60 -22.10   0.50    1.00    -- -110.12  88.31-103.97  233
 32  \f    -20.08 339.92   0.50    1.00  19.35  45.19  59.25    --   720
 33  \f   -339.92  20.08   0.50    1.00 -84.46-110.12 -59.25    --   720
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0249673000
_diffrn_orient_matrix_UB_12      -0.0897052000
_diffrn_orient_matrix_UB_13      0.0445196000
_diffrn_orient_matrix_UB_21      0.1495179000
_diffrn_orient_matrix_UB_22      0.0296892000
_diffrn_orient_matrix_UB_23      0.0086553000
_diffrn_orient_matrix_UB_31      0.0425213000
_diffrn_orient_matrix_UB_32      0.1198028000
_diffrn_orient_matrix_UB_33      0.0402333000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1754
_diffrn_reflns_av_unetI/netI     0.1311
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            66728
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.142
_diffrn_reflns_theta_min         1.739
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.124a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.059
_exptl_crystal_description       irregular
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     671
_refine_ls_number_reflns         11497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1853
_refine_ls_R_factor_gt           0.1054
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2927
_refine_ls_wR_factor_ref         0.3545
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5399
_reflns_number_total             11497
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6nj00521g2.cif
_cod_data_source_block           cu_cbn120240621_autored
_cod_depositor_comments          'Adding full bibliography for 7064373.cif.'
_cod_database_code               7064373
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C50 H56 B20 O4'
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C37(H37A,H37B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C16(H16), C17(H17), C20(H20),
 C21(H21), C23(H23), C28(H28), C29(H29), C32(H32), C33(H33), C34(H34), C41(H41),
  C42(H42), C45(H45), C46(H46), C48(H48)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C24(H24A,H24B,H24C), C38(H38A,H38B,H38C), C49(H49A,H49B,
 H49C)
2.d Boron cage BH refined with riding coordinates:
 B1(H1), B2(H2), B3(H3A), B4(H4A), B5(H5), B6(H6), B7(H7A), B8(H8A), B9(H9A),
 B10(H10), B11(H11), B12(H12), B13(H13), B14(H14), B15(H15), B16(H16A),
 B17(H17A), B18(H18), B19(H19), B20(H20A)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.136
_oxdiff_exptl_absorpt_empirical_full_min 0.490