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_7135498
_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 H12 N2 O'
_chemical_formula_sum            'C17 H12 N2 O'
_chemical_formula_weight         260.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.1777(2)
_cell_length_b                   19.0358(12)
_cell_length_c                   24.8301(14)
_cell_measurement_reflns_used    4346
_cell_measurement_temperature    100.01(11)
_cell_measurement_theta_max      71.5400
_cell_measurement_theta_min      4.5700
_cell_volume                     2447.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.121a (Rigaku OD, 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      100.01(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.955
_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  77.00   0.50    0.50    --   61.94-125.00   0.00   52
  2  \w     26.00  77.00   0.50    0.50    --   61.94-125.00  30.00  102
  3  \w     28.00  77.00   0.50    0.50    --   61.94-125.00  60.00   98
  4  \w     31.00  76.00   0.50    0.50    --   61.94-125.00  90.00   90
  5  \w     26.00  52.00   0.50    0.50    --   61.94-125.00 150.00   52
  6  \w     47.00  81.00   0.50    0.50    --   71.27-125.00  90.00   68
  7  \w     51.00  84.00   0.50    0.50    --   71.27-125.00  30.00   66
  8  \w     65.00  90.00   0.50    0.50    --   74.13-125.00  30.00   50
  9  \w     63.00  90.00   0.50    0.50    --   74.13-125.00  60.00   54
 10  \w     42.00  73.00   0.50    0.50    --   74.13-125.00   0.00   62
 11  \w     50.00  85.00   0.50    0.50    --   74.13-125.00 -30.00   70
 12  \w     51.00  89.00   0.50    0.50    --   74.13-125.00-180.00   76
 13  \w     27.00  52.00   0.50    0.50    --   14.00  16.00 -57.29   50
 14  \w     57.00  84.00   0.50    0.50    --   61.94  15.00 -60.00   54
 15  \w     55.00  95.00   0.50    0.50    --   61.94  15.00   0.00   80
 16  \w     58.00  84.00   0.50    0.50    --   61.94  15.00  60.00   52
 17  \w     64.00  94.00   0.50    0.50    --   61.94  15.00 120.00   60
 18  \w     62.00  88.00   0.50    0.50    --   61.94  15.00 150.00   52
 19  \w     61.00  86.00   0.50    0.50    --   61.94  15.00  30.00   50
 20  \w     71.00  97.00   0.50    0.50    --   71.27  15.00 120.00   52
 21  \w     62.00  94.00   0.50    0.50    --   61.94  15.00 -90.00   64
 22  \w     57.00  98.00   0.50    0.50    --   61.94  15.00-120.00   82
 23  \w     60.00  88.00   0.50    0.50    --   61.94  15.00-150.00   56
 24  \w     80.00 106.00   0.50    0.50    --   71.27  15.00-150.00   52
 25  \w     67.00 106.00   0.50    0.50    --   74.13  15.00-180.00   78
 26  \w     73.00  99.00   0.50    0.50    --   74.13  15.00-150.00   52
 27  \w     78.00 112.00   0.50    0.50    --   74.13  15.00-120.00   68
 28  \w     69.00 108.00   0.50    0.50    --   74.13  15.00 -60.00   78
 29  \w     77.00 115.00   0.50    0.50    --   74.13  15.00 -30.00   76
 30  \w     68.00 107.00   0.50    0.50    --   74.13  15.00  60.00   78
 31  \w     75.00 103.00   0.50    0.50    --   74.13  15.00  90.00   56
;
_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      0.0868139000
_diffrn_orient_matrix_UB_12      -0.0683858000
_diffrn_orient_matrix_UB_13      0.0277049000
_diffrn_orient_matrix_UB_21      0.0021595000
_diffrn_orient_matrix_UB_22      -0.0375655000
_diffrn_orient_matrix_UB_23      -0.0550018000
_diffrn_orient_matrix_UB_31      0.2846574000
_diffrn_orient_matrix_UB_32      0.0212130000
_diffrn_orient_matrix_UB_33      -0.0079771000
_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  0.1212
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16744
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.869
_diffrn_reflns_theta_min         4.646
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34733
_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_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       needle
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.319
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.319
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.1024
_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^)+(0.0736P)^2^+4.6778P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2277
_refine_ls_wR_factor_ref         0.2328
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2153
_reflns_number_total             2344
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06628j2.cif
_cod_data_source_block           np_bop-oh_auto
_cod_database_code               7135498
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S Cl'
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.913
_reflns_odcompleteness_completeness 98.42
_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:
 N2(H2), N1(H1), C2(H2a), C1(H1a), C6(H6), C3(H3), C9(H9), C15(H15), C13(H13),
 C11(H11), C14(H14), C10(H10)
;
_shelx_res_checksum              23489
_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 2.912
_oxdiff_exptl_absorpt_empirical_full_min 0.375