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_7135501
_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         '0.2(C23 H15 B F2 N2 O)'
_chemical_formula_sum            'C4.6 H3 B0.2 F0.4 N0.4 O0.2'
_chemical_formula_weight         76.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-03-13
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-10-29 deposited with the CCDC.	2025-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                94.5670(10)
_cell_angle_beta                 97.121(2)
_cell_angle_gamma                90.226(2)
_cell_formula_units_Z            8
_cell_length_a                   10.1116(2)
_cell_length_b                   11.6324(2)
_cell_length_c                   30.3083(5)
_cell_measurement_reflns_used    24074
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.0590
_cell_measurement_theta_min      2.9610
_cell_volume                     3525.85(11)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_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    -97.00 -65.00   0.50    0.15    --  -99.00  77.00  60.00   64
  2  \w    -63.00 -36.00   0.50    0.15    --  -99.00  77.00  60.00   54
  3  \w    -68.00 -27.00   0.50    0.15    --  -99.00  77.00-120.00   82
  4  \w   -101.00 -27.00   0.50    0.15    --  -99.00  77.00-180.00  148
  5  \w    -65.00 -27.00   0.50    0.15    --  -99.00  61.00-120.00   76
  6  \w    -70.00 -33.00   0.50    0.15    --  -99.00  61.00   0.00   74
  7  \w    -69.00 -38.00   0.50    0.15    --  -99.00  61.00  30.00   62
  8  \w    -70.00 -26.00   0.50    0.15    --  -99.00  61.00  60.00   88
  9  \w    -70.00 -26.00   0.50    0.15    --  -99.00  61.00 150.00   88
 10  \w    -25.00  29.00   0.50    0.08    --  -45.87  19.00  30.00  108
 11  \w     23.00 119.00   0.50    0.08    --   45.87  77.00 -60.00  192
 12  \w     83.00 147.00   0.50    0.15    --   99.00  15.00  30.00  128
 13  \w     85.00 162.00   0.50    0.15    --   99.00  30.00 -30.00  154
 14  \w     84.00 164.00   0.50    0.15    --   99.00   0.00-180.00  160
 15  \w    120.00 172.00   0.50    0.15    --   99.00  45.00-180.00  104
 16  \w     83.00 169.00   0.50    0.15    --   99.00 125.00-180.00  172
 17  \w     84.00 123.00   0.50    0.15    --   99.00 137.00-161.00   78
 18  \w     71.00  96.00   0.50    0.08    --   45.87 137.00-161.00   50
 19  \w     98.00 124.00   0.50    0.15    --   99.00 131.00  22.00   52
 20  \w    -13.00  26.00   0.50    0.08    --   45.87 -19.00-150.00   78
 21  \w    -25.00  62.00   0.50    0.08    --   45.87 -57.00-180.00  174
 22  \w     27.00  52.00   0.50    0.15    --   99.00 -45.00-180.00   50
 23  \w     33.00  61.00   0.50    0.15    --   99.00 -61.00-150.00   56
 24  \w     27.00  64.00   0.50    0.15    --   99.00 -61.00 -90.00   74
 25  \w     29.00  68.00   0.50    0.15    --   99.00 -61.00  60.00   78
 26  \w     40.00  68.00   0.50    0.08    --   45.87-137.00 136.00   56
 27  \w     93.00 118.00   0.50    0.15    --   99.00-137.00 136.00   50
 28  \w     75.00 110.00   0.50    0.15    --   99.00-125.00   0.00   70
 29  \w     44.00 104.00   0.50    0.15    --   99.00 -94.00 -30.00  120
 30  \w     28.00 115.00   0.50    0.15    --   99.00-131.00 -47.00  174
 31  \w     49.00 103.00   0.50    0.15    --   99.00 -94.00-180.00  108
 32  \w     51.00  95.00   0.50    0.08    --   45.87-131.00 -47.00   88
 33  \w     72.00 101.00   0.50    0.15    --   99.00 -94.00 120.00   58
 34  \w     28.00  56.00   0.50    0.15    --   99.00 -94.00 120.00   56
 35  \w     45.00  95.00   0.50    0.15    --   99.00 -94.00 150.00  100
 36  \w    -85.00 -60.00   0.50    0.08    --  -45.87 137.00-161.00   50
 37  \w   -117.00 -71.00   0.50    0.15    --  -99.00 137.00-161.00   92
 38  \w    -65.00 -39.00   0.50    0.08    --  -45.87 131.00  22.00   52
 39  \w   -116.00 -84.00   0.50    0.15    --  -99.00 131.00  22.00   64
 40  \w   -174.00 -99.00   0.50    0.15    --  -99.00 -15.00 120.00  150
 41  \w   -144.00-119.00   0.50    0.15    --  -99.00-137.00 136.00   50
 42  \w   -119.00 -75.00   0.50    0.08    --  -45.87-137.00 136.00   88
 43  \w   -116.00 -80.00   0.50    0.08    --  -45.87-131.00 -47.00   72
 44  \w   -145.00-120.00   0.50    0.15    --  -99.00-131.00 -47.00   50
 45  \w   -111.00 -73.00   0.50    0.15    --  -99.00-131.00 -47.00   76
 46  \w   -113.00 -88.00   0.50    0.15    --  -99.00-125.00-180.00   50
 47  \w   -152.00-126.00   0.50    0.15    --  -99.00-125.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0523947000
_diffrn_orient_matrix_UB_12      -0.0090845000
_diffrn_orient_matrix_UB_13      -0.0501142000
_diffrn_orient_matrix_UB_21      -0.1441527000
_diffrn_orient_matrix_UB_22      -0.0054144000
_diffrn_orient_matrix_UB_23      0.0113292000
_diffrn_orient_matrix_UB_31      -0.0073363000
_diffrn_orient_matrix_UB_32      0.1324505000
_diffrn_orient_matrix_UB_33      0.0011884000
_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  0.0657
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            48774
_diffrn_reflns_theta_full        73.41
_diffrn_reflns_theta_max         73.41
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1045
_refine_ls_number_reflns         13651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0797
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1268P)^2^+5.8888P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2608
_refine_ls_wR_factor_ref         0.2691
_reflns_number_gt                10930
_reflns_number_total             13651
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d5cc06628j2.cif
_cod_data_source_block           np-oph_auto
_cod_original_formula_sum        'C4.60 H3 B0.20 F0.40 N0.40 O0.20'
_cod_database_code               7135501
_chemical_oxdiff_formula         'C H O N  B F'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011),
 C012(H012), C013(H013), C014(H014), C015(H015), C018(H018), C01A(H01A),
 C01B(H01B), C01C(H01C), C01D(H01D), C01E(H01E), C01F(H01F), C01G(H01G),
 C01I(H01I), C01J(H01J), C01K(H01K), C01L(H01L), C01M(H01M), C01N(H01N),
 C01R(H01R), C01S(H01S), C01V(H01V), C01W(H01W), C01Z(H01Z), C020(H020),
 C021(H021), C022(H022), C024(H024), C025(H025), C029(H029), C02A(H02A),
 C02B(H02B), C02C(H02C), C02D(H02D), C02E(H02E), C02F(H02F), C02H(H02H),
 C02I(H02I), C02K(H02K), C02L(H02L), C02N(H02N), C02P(H02P), C02Q(H02Q),
 C02R(H02R), C02S(H02S), C02T(H02T), C02U(H02U), C02X(H02X), C02Y(H02Y),
 C02Z(H02Z), C030(H030), C031(H031), C032(H032), C033(H033), C034(H034)
;
_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 2.128
_oxdiff_exptl_absorpt_empirical_full_min 0.451