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_7135499
_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         '0.25(C17 H10 B Cl F2 N2)'
_chemical_formula_sum            'C4.25 H2.5 B0.25 Cl0.25 F0.5 N0.5'
_chemical_formula_weight         81.63
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-08-11
_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                90.00
_cell_angle_beta                 90.3969(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   8.72703(19)
_cell_length_b                   7.57330(14)
_cell_length_c                   21.4926(4)
_cell_measurement_reflns_used    4791
_cell_measurement_temperature    297.7(2)
_cell_measurement_theta_max      73.6450
_cell_measurement_theta_min      6.2060
_cell_volume                     1420.46(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.7(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -10.00  30.00   0.50    0.50    --    0.00 -82.00  90.00   80
  2  \w    -23.00  30.00   0.50    0.50    --    0.00 -82.00  30.00  106
  3  \w    -30.00  -5.00   0.50    0.50    --    0.00 -82.00-180.00   50
  4  \w    -32.00  13.00   0.50    0.50    --    0.00 -82.00 150.00   90
  5  \w     11.00  93.00   0.50    0.50    --   95.80 -15.00-150.00  164
  6  \w     24.00 113.00   0.50    0.50    --   95.80 -61.00-180.00  178
  7  \w      6.00  31.00   0.50    0.50    --   95.80 -15.00  90.00   50
  8  \w     10.00  35.00   0.50    0.50    --   95.80 -30.00-150.00   50
  9  \w     62.00  88.00   0.50    0.50    --   95.80 -30.00-150.00   52
 10  \w     91.00 180.00   0.50    0.50    --   95.80  30.00-180.00  178
 11  \w     34.00 111.00   0.50    0.50    --   95.80 -45.00   0.00  154
 12  \w     37.00 119.00   0.50    0.50    --   95.80 -77.00-180.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1479913000
_diffrn_orient_matrix_UB_12      0.0213964000
_diffrn_orient_matrix_UB_13      0.0387811000
_diffrn_orient_matrix_UB_21      -0.0946586000
_diffrn_orient_matrix_UB_22      0.0690111000
_diffrn_orient_matrix_UB_23      0.0550728000
_diffrn_orient_matrix_UB_31      -0.0176760000
_diffrn_orient_matrix_UB_32      -0.1902437000
_diffrn_orient_matrix_UB_33      0.0243982000
_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  0.0233
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6237
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         4.11
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.579
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38206
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0050(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+0.3773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                2282
_reflns_number_total             2495
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d5cc06628j2.cif
_cod_data_source_block           ybl-fb
_cod_original_formula_sum        'C4.25 H2.50 B0.25 Cl0.25 F0.50 N0.50'
_cod_database_code               7135499
_chemical_oxdiff_formula         'C H O N B F'
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15)
;
_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 1.778
_oxdiff_exptl_absorpt_empirical_full_min 0.489