Sulfur-bridged annulated BODIPYs: synthesis, structure and photophysical properties
Zhang, Yongli; Fu, Xiong; Li, Jie; Guo, Kaiwen; Wen, Hanyu; Guo, Tingting; Li, Xiangguang; Yang, Yanhua; Gao, Shulin; New Journal of Chemistry 49 (2025) 11326–11333; doi:10.1039/D5NJ01481F

data_7063832
_publ_section_title
;
 Sulfur-bridged annulated BODIPYs: synthesis, structure and photophysical
 properties
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11326
_journal_page_last               11333
_journal_paper_doi               10.1039/D5NJ01481F
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C19 H17 B F2 N2 S'
_chemical_formula_sum            'C19 H17 B F2 N2 S'
_chemical_formula_weight         354.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-05-16
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-09-03 deposited with the CCDC.	2025-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.209(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1383(2)
_cell_length_b                   11.5671(3)
_cell_length_c                   19.5512(5)
_cell_measurement_reflns_used    4348
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      67.761
_cell_measurement_theta_min      4.448
_cell_volume                     1604.86(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0431
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13426
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.919
_diffrn_reflns_theta_min         4.448
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.012
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1175 before and 0.0520 after correction.
The Ratio of minimum to maximum transmission is 0.8452.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         2908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0514P)^2^+0.4564P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2431
_reflns_number_total             2908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj01481f2.cif
_cod_data_source_block           cu_20230516_ys_kmxy_lil_1_0m
_cod_depositor_comments
'Adding full bibliography for 7063831--7063832.cif.'
_cod_database_code               7063832
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.794
_shelx_estimated_absorpt_t_min   0.752
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(S1B)=Sof(H5)=Sof(H13)=1-FVAR(1)
 Sof(S1A)=Sof(H1)=Sof(H9)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C13(H13)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
;
_shelx_res_checksum              79555
_olex2_submission_special_instructions 'No special instructions were received'