A facile strategy for π-extended BOPYINs: transformation into six-membered BODIPY analogues and their optical properties.
Zhang, Ziyi; Li, Xi; Feng, Yilin; Gao, Xin; Qi, Yong; Yan, Jiaying; Zhang, Nuonuo; Chemical communications (Cambridge, England) 62 (2026) 2659–2663; doi:10.1039/d5cc06628j

data_7135500
_publ_section_title
;
 A facile strategy for &#x3c0;-extended BOPYINs: transformation into
 six-membered BODIPY analogues and their optical properties.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2659
_journal_page_last               2663
_journal_paper_doi               10.1039/d5cc06628j
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C17 H11 B F2 N2 O'
_chemical_formula_sum            'C17 H11 B F2 N2 O'
_chemical_formula_weight         308.09
_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             2025-06-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2025-10-29 deposited with the CCDC.	2025-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.208(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6144(2)
_cell_length_b                   8.74800(10)
_cell_length_c                   16.3991(3)
_cell_measurement_reflns_used    6529
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      72.6400
_cell_measurement_theta_min      4.7440
_cell_volume                     1330.97(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.121a 64-bit (release 24-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_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     56.00  81.00   0.50    0.05    --   62.27  15.00-180.00   50
  2  \w     55.00  80.00   0.50    0.05    --   62.27  15.00-150.00   50
  3  \w     57.00  90.00   0.50    0.05    --   62.27  15.00 -90.00   66
  4  \w     62.00  88.00   0.50    0.05    --   62.27  15.00 -60.00   52
  5  \w     61.00 101.00   0.50    0.05    --   62.27  15.00 -30.00   80
  6  \w     78.00 106.00   0.50    0.05    --   71.29  15.00 -60.00   56
  7  \w     73.00 100.00   0.50    0.05    --   62.27  15.00   0.00   54
  8  \w     68.00  94.00   0.50    0.05    --   62.27  15.00  30.00   52
  9  \w     67.00  95.00   0.50    0.05    --   62.27  15.00  60.00   56
 10  \w     71.00 109.00   0.50    0.05    --   74.30  15.00  90.00   76
 11  \w     74.00 100.00   0.50    0.05    --   74.30  15.00  60.00   52
 12  \w     68.00 100.00   0.50    0.05    --   74.30  15.00  30.00   64
 13  \w     66.00  92.00   0.50    0.05    --   71.29  15.00   0.00   52
 14  \w     72.00  97.00   0.50    0.05    --   74.30  15.00 150.00   50
 15  \w     74.00 109.00   0.50    0.05    --   74.30  15.00 -30.00   70
 16  \w     77.00 115.00   0.50    0.05    --   74.30  15.00-150.00   76
 17  \w     79.00 106.00   0.50    0.05    --   74.30  15.00-180.00   54
 18  \w     25.00  50.00   0.50    0.05    --   62.27-125.00-180.00   50
 19  \w     58.00  89.00   0.50    0.05    --   74.30-125.00-180.00   62
 20  \w     28.00  60.00   0.50    0.05    --   62.27-125.00-150.00   64
 21  \w     26.00  76.00   0.50    0.05    --   62.27-125.00-120.00  100
 22  \w     53.00  78.00   0.50    0.05    --   74.30-125.00-150.00   50
 23  \w     45.00  71.00   0.50    0.05    --   71.29-125.00-120.00   52
 24  \w     37.00  78.00   0.50    0.05    --   74.30-125.00 -90.00   82
 25  \w     25.00  60.00   0.50    0.05    --   62.27-125.00 150.00   70
 26  \w     38.00  90.00   0.50    0.05    --   74.30-125.00 150.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0570996000
_diffrn_orient_matrix_UB_12      0.0583403000
_diffrn_orient_matrix_UB_13      -0.0737946000
_diffrn_orient_matrix_UB_21      0.1529656000
_diffrn_orient_matrix_UB_22      -0.0529036000
_diffrn_orient_matrix_UB_23      0.0466770000
_diffrn_orient_matrix_UB_31      -0.0304068000
_diffrn_orient_matrix_UB_32      -0.1574673000
_diffrn_orient_matrix_UB_33      -0.0430311000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8972
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.821
_diffrn_reflns_theta_min         4.766
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.969
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0431P)^2^+0.4603P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0834
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2371
_reflns_number_total             2572
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06628j2.cif
_cod_data_source_block           np_oh_auto
_cod_database_code               7135500
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C  H O N B F'
_shelx_estimated_absorpt_t_max   0.893
_shelx_estimated_absorpt_t_min   0.876
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N21(H21), C15(H15), C18(H18), C4(H4), C10(H10), C6(H6), C8(H8), C5(H5),
 C19(H19), C9(H9), C20(H20)
;
_shelx_res_checksum              9766
_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 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.881