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_7719031
_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 H15 B Br F2 N3'
_chemical_formula_sum            'C20 H15 B Br F2 N3'
_chemical_formula_weight         426.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_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                90
_cell_angle_beta                 101.314(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4783(2)
_cell_length_b                   10.7900(3)
_cell_length_c                   20.1223(6)
_cell_measurement_reflns_used    5848
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      24.7380
_cell_measurement_theta_min      2.0490
_cell_volume                     1805.03(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  'SHELXL 2018/3 (Sheldrick, 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_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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   -126.27 154.23   1.50   10.00  72.69 -18.16  31.50    --   187
  2  \w    -76.17   6.33   1.50   10.00    --  -18.16  89.85 -32.66   55
  3  \w   -122.88  22.62   1.50   10.00    --  -18.16 -59.25  20.08   97
  4  \w   -122.88  22.62   1.50   10.00    --  -18.16 -59.25 173.08   97
  5  \w    -76.17   6.33   1.50   10.00    --  -18.16  89.85  18.34   55
;
_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      -0.0090892000
_diffrn_orient_matrix_UB_12      -0.0070951000
_diffrn_orient_matrix_UB_13      0.0340761000
_diffrn_orient_matrix_UB_21      -0.0752986000
_diffrn_orient_matrix_UB_22      0.0307843000
_diffrn_orient_matrix_UB_23      -0.0077741000
_diffrn_orient_matrix_UB_31      -0.0391116000
_diffrn_orient_matrix_UB_32      -0.0576595000
_diffrn_orient_matrix_UB_33      -0.0083615000
_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  0.0715
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23017
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.064
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.306
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56374
_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 pinkish pink'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   pinkish
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.568
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0675P)^2^+4.1677P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1359
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2661
_reflns_number_total             3160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt00431d2.cif
_cod_data_source_block           mr_pc_7br_autored
_cod_database_code               7719031
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.802
_shelx_estimated_absorpt_t_min   0.545
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 N3(H006), C6(H00D), C14(H00F), C15(H00H), C12(H00I), C10(H00J), C4(H00K),
 C7(H00L), C3(H00M), C18(H00N), C19(H00O), C11(H00P)
1.b Idealised Me refined as rotating group:
 C1(H00A,H00B,H00C)
;
_shelx_res_checksum              23847
_shelx_hkl_checksum              76729
_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 1.558
_oxdiff_exptl_absorpt_empirical_full_min 0.650