Synthesis, structure, spectral and redox properties of 3-pyrrolyl BODIPYs containing one to eight bromides at the pyrrole carbons.
Chauhan, Pinky; Ravikanth, Mangalampalli; Dalton transactions (Cambridge, England : 2003) 54 (2025) 7465–7474; doi:10.1039/d5dt00431d

data_7719035
_publ_section_title
;
 Synthesis, structure, spectral and redox properties of 3-pyrrolyl BODIPYs
 containing one to eight bromides at the pyrrole carbons.
;
_journal_issue                   18
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7465
_journal_page_last               7474
_journal_paper_doi               10.1039/d5dt00431d
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C20 H10 B Br6 F2 N3, 0.025[C6H14]'
_chemical_formula_sum            'C20 H10 B Br6 F2 N3'
_chemical_formula_weight         822.719
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-27
_audit_creation_method
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_audit_update_record
;
2025-01-27 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                73.539(4)
_cell_angle_beta                 72.537(4)
_cell_angle_gamma                85.421(4)
_cell_formula_units_Z            2
_cell_length_a                   8.3985(4)
_cell_length_b                   10.9871(4)
_cell_length_c                   13.8246(6)
_cell_measurement_reflns_used    19483
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      32.8570
_cell_measurement_theta_min      1.6100
_cell_volume                     1166.98(9)
_computing_cell_refinement       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection
'PROGRAM:BIS V6.2.16/2021-10-22 && APEX4 2021.4-0                                '
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement
'olex2.refine 1.5-ac6-016 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.9647
_diffrn_measured_fraction_theta_max 0.9647
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    154.25 334.25   1.00    1.00 -25.75   0.00  73.76    --   180
  2  \f   -349.73  10.27   1.00   10.00  21.81 -27.45 -31.50    --   360
  3  \w    -85.46   6.54   1.00   10.00    --  -27.45  89.85 171.34   92
  4  \w    -85.46   6.54   1.00   10.00    --  -27.45  89.85 -32.66   92
  5  \w   -132.17  13.83   1.00   10.00    --  -27.45 -59.25-135.92  146
  6  \w   -132.17  13.83   1.00   10.00    --  -27.45 -59.25  20.08  146
  7  \w    -85.46   6.54   1.00   10.00    --  -27.45  89.85  69.33   92
  8  \w   -132.17  13.83   1.00   10.00    --  -27.45 -59.25 173.08  146
  9  \w    -85.46   6.54   1.00   10.00    --  -27.45  89.85-137.67   92
 10  \w    -85.46   6.54   1.00   10.00    --  -27.45  89.85  18.34   92
 11  \w   -132.17  13.83   1.00   10.00    --  -27.45 -59.25  71.08  146
 12  \w   -132.17  13.83   1.00   10.00    --  -27.45 -59.25 -84.92  146
 13  \w   -132.17  13.83   1.00   10.00    --  -27.45 -59.25 -33.92  146
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0275000000
_diffrn_orient_matrix_UB_12      0.0554452000
_diffrn_orient_matrix_UB_13      0.0167133000
_diffrn_orient_matrix_UB_21      -0.0805983000
_diffrn_orient_matrix_UB_22      -0.0273436000
_diffrn_orient_matrix_UB_23      0.0261045000
_diffrn_orient_matrix_UB_31      0.0242204000
_diffrn_orient_matrix_UB_32      -0.0266419000
_diffrn_orient_matrix_UB_33      0.0465270000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2180
_diffrn_reflns_av_unetI/netI     0.1076
_diffrn_reflns_Laue_measured_fraction_full 0.9647
_diffrn_reflns_Laue_measured_fraction_max 0.9647
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            58232
_diffrn_reflns_point_group_measured_fraction_full 0.9647
_diffrn_reflns_point_group_measured_fraction_max 0.9647
_diffrn_reflns_theta_full        24.9980
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.61
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    10.352
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic bluish violet'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    2.341
_exptl_crystal_description       block
_exptl_crystal_F_000             768.482
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.3665
_refine_diff_density_min         -1.2964
_refine_diff_density_rms         0.3481
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             12.6872
_refine_ls_goodness_of_fit_ref   1.0311
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3960
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.0303
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0726
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+48.7646P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1970
_refine_ls_wR_factor_ref         0.1983
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3680
_reflns_number_total             3960
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5dt00431d2.cif
_cod_data_source_block           MR_PC_6_BR_R_autored
_cod_database_code               7719035
_reflns_odcompleteness_completeness 92.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.96
_olex2_refinement_description
;
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.260
_oxdiff_exptl_absorpt_empirical_full_min 0.464