A novel boron-stereogenic fluorophore with dual-state circular polarization luminescence via a self-dispersing strategy
Yu, Changjiang; Cheng, Chao; Liu, Zhangzhan; Ni, Zhigang; Zhao, Zujin; Lu, Hua; Hao, Erhong; Jiao, Lijuan; Chemical Science 16 (2025) 7971–7980; doi:10.1039/D5SC01025J

data_1574271
_publ_section_title
;
 A novel boron-stereogenic fluorophore with dual-state circular
 polarization luminescence via a self-dispersing strategy
;
_journal_issue                   18
_journal_name_full               'Chemical Science'
_journal_page_first              7971
_journal_page_last               7980
_journal_paper_doi               10.1039/D5SC01025J
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C34 H31 B2 N3 O2'
_chemical_formula_sum            'C34 H31 B2 N3 O2'
_chemical_formula_weight         535.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc29198y
_audit_creation_date             2021-10-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_audit_update_record
;
2021-10-19 deposited with the CCDC.	2025-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.164(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.5820(5)
_cell_length_b                   43.689(2)
_cell_length_c                   15.6237(8)
_cell_measurement_reflns_used    9588
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.06
_cell_measurement_theta_min      2.83
_cell_volume                     6540.5(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0841
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       53
_diffrn_reflns_limit_k_min       -53
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            109854
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.292
_diffrn_reflns_theta_min         2.828
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.524
_exptl_absorpt_correction_T_max  0.7654
_exptl_absorpt_correction_T_min  0.5326
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_description       cube
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 9284 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.27(8)
_refine_ls_extinction_coef       0.00057(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1443
_refine_ls_number_reflns         25164
_refine_ls_number_restraints     690
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0743
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1360P)^2^+1.9049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2013
_refine_ls_wR_factor_ref         0.2108
_reflns_Friedel_coverage         0.970
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                22183
_reflns_number_total             25164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01025j2.cif
_cod_data_source_block           1f
_cod_depositor_comments
'Adding full bibliography for 1574271--1574277.cif.'
_cod_original_cell_volume        6540.6(6)
_cod_database_code               1574271
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.916
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.808(2) 0.192(2)
2. 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
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C5AA) \\sim Ueq, Uanis(C34A) \\sim Ueq, Uanis(C29A) \\sim Ueq,
Uanis(C30A) \\sim Ueq, Uanis(C31A) \\sim Ueq, Uanis(C32A) \\sim Ueq: with sigma
of 0.1 and sigma for terminal atoms of 0.2
Uanis(C2AA) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C4AA) \\sim Ueq, Uanis(C7AA) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C2AA) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C18A) \\sim Ueq, Uanis(C17A)
\\sim Ueq, Uanis(C22A) \\sim Ueq, Uanis(C1AA) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.2
Uanis(C34A) \\sim Ueq, Uanis(C29A) \\sim Ueq, Uanis(C5AA) \\sim Ueq,
Uanis(C32A) \\sim Ueq, Uanis(C31A) \\sim Ueq, Uanis(C30A) \\sim Ueq: with sigma
of 0.1 and sigma for terminal atoms of 0.2
Uanis(C22B) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C7AA) \\sim Ueq, Uanis(C19B)
\\sim Ueq, Uanis(C18B) \\sim Ueq, Uanis(C17B) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.2
Uanis(C23D) \\sim Ueq, Uanis(C28D) \\sim Ueq, Uanis(C27D) \\sim Ueq,
Uanis(C26D) \\sim Ueq, Uanis(C25D) \\sim Ueq, Uanis(C24D) \\sim Ueq: with sigma
of 0.1 and sigma for terminal atoms of 0.2
Uanis(C21C) \\sim Ueq, Uanis(C20C) \\sim Ueq, Uanis(C4AA) \\sim Ueq,
Uanis(C0AA) \\sim Ueq, Uanis(C17C) \\sim Ueq, Uanis(C22C) \\sim Ueq: with sigma
of 0.1 and sigma for terminal atoms of 0.2
5. Rigid body (RIGU) restrains
 C29D, C30D, C31D, C32D, C33D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Secondary CH2 refined with riding coordinates:
 C6D(H6DA,H6DB), C7B(H7BA,H7BB), C7C(H7CA,H7CB), C8A(H8AA,H8AB)
6.b Aromatic/amide H refined with riding coordinates:
 C9D(H9D), C12D(H12D), C13D(H13D), C14D(H14D), C15D(H15D), C18D(H18D),
 C19D(H19D), C20D(H20D), C21D(H21D), C22D(H22D), C24D(H24D), C25D(H25D),
 C26D(H26D), C27D(H27D), C28D(H28D), C30D(H30D), C31D(H31D), C32D(H32D),
 C33D(H33D), C6A(H6A), C6B(H6B), C6C(H6C), C12A(H12A), C12B(H12B), C12C(H12C),
 C13A(H13A), C13B(H13B), C13C(H13C), C14A(H14A), C14B(H14B), C14C(H14C),
 C15A(H15A), C15B(H15B), C15C(H15C), C17C(H17C), C18A(H18A), C18B(H18B),
 C19B(H19B), C20C(H20C), C21C(H21C), C22A(H22A), C22B(H22B), C24B(H24B),
 C25B(H25B), C26B(H26B), C27B(H27B), C28B(H28B), C24C(H24C), C25C(H25C),
 C26C(H26C), C27C(H27C), C28A(H28A), C27A(H27A), C26A(H26A), C25A(H25A),
 C24A(H24A), C28C(H28C), C30B(H30B), C30C(H30C), C31B(H31B), C31C(H31C),
 C32B(H32B), C32C(H32C), C33B(H33B), C33C(H33C), C34A(H34A), C5AA(H5AA),
 C32A(H32A), C31A(H31A), C30A(H30A), C34B(H34B), C34C(H34C), C0AA(H0AA),
 C2AA(H2AA), C2(H2), C1AA(H1AD), C1(H1), C4AA(H4AA), C6AA(H6AA), C7AA(H7AA)
6.c Fitted hexagon refined as free rotating group:
 C18D(C19D,C20D,C21D,C22D,C17D), C24B(C25B,C26B,C27B,C28B,C23B), C28A(C27A,
 C26A,C25A,C24A,C23A), C34A(C5AA,C32A,C31A,C30A,C29A)
6.d Idealised Me refined as rotating group:
 C1D(H1DA,H1DB,H1DC), C5D(H5DA,H5DB,H5DC), C7D(H7DA,H7DB,H7DC), C1A(H1AA,H1AB,
 H1AC), C1B(H1BA,H1BB,H1BC), C1C(H1CA,H1CB,H1CC), C7A(H7AB,H7AC,H7AD), C8C(H8CA,
 H8CB,H8CC), C9A(H9AA,H9AB,H9AC), C9B(H9BA,H9BB,H9BC), C9C(H9CA,H9CB,H9CC),
 C3AA(H3AA,H3AB,H3AC)
;
_shelx_res_checksum              81832
_shelx_fab_checksum              3507
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'