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_7719032
_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 H14 B Br2 F2 N3'
_chemical_formula_sum            'C20 H14 B Br2 F2 N3'
_chemical_formula_weight         504.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 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                 98.240(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8062(3)
_cell_length_b                   21.3167(5)
_cell_length_c                   8.1321(2)
_cell_measurement_reflns_used    4155
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.2940
_cell_measurement_theta_min      1.9090
_cell_volume                     1853.91(8)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -122.88  22.72   1.30   10.00    --  -18.16 -59.25  71.08  112
  2  \w   -122.88  22.72   1.30   10.00    --  -18.16 -59.25 -84.92  112
  3  \w   -122.88  22.72   1.30   10.00    --  -18.16 -59.25-135.92  112
  4  \w   -122.88  22.72   1.30   10.00    --  -18.16 -59.25  20.08  112
  5  \w   -122.88  22.72   1.30   10.00    --  -18.16 -59.25 122.08  112
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0031427000
_diffrn_orient_matrix_UB_12      -0.0316523000
_diffrn_orient_matrix_UB_13      0.0272338000
_diffrn_orient_matrix_UB_21      0.0249071000
_diffrn_orient_matrix_UB_22      0.0099901000
_diffrn_orient_matrix_UB_23      0.0812048000
_diffrn_orient_matrix_UB_31      -0.0613907000
_diffrn_orient_matrix_UB_32      0.0024286000
_diffrn_orient_matrix_UB_33      0.0206893000
_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  0.0574
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12219
_diffrn_reflns_point_group_measured_fraction_full 0.868
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.911
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.403
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50826
_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    1.809
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1013 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.015(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2835
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0382P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0753
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.735
_reflns_Friedel_fraction_max     0.735
_reflns_number_gt                2636
_reflns_number_total             2835
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt00431d2.cif
_cod_data_source_block           mr_kcb_14_autored
_cod_database_code               7719032
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.667
_shelx_estimated_absorpt_t_min   0.352
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H3A), C6(H4), C4(H6), C3(H7), C14(H10), C15(H11), C18(H14),
 C19(H15), C10(H18), C11(H19)
1.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              36043
_shelx_hkl_checksum              49073
_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 2.438
_oxdiff_exptl_absorpt_empirical_full_min 0.564