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_7719034
_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 H12 B Br4 F2 N3'
_chemical_formula_sum            'C20 H12 B Br4 F2 N3'
_chemical_formula_weight         662.773
_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     iterative
_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                113.044(9)
_cell_angle_beta                 98.397(9)
_cell_angle_gamma                101.444(7)
_cell_formula_units_Z            2
_cell_length_a                   7.8058(8)
_cell_length_b                   11.8722(8)
_cell_length_c                   12.6039(15)
_cell_measurement_reflns_used    2458
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      20.8190
_cell_measurement_theta_min      1.9270
_cell_volume                     1020.5(2)
_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
'olex2.solve 1.5-ac6-016 (Bourhis et al., 2015)'
_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 0.9986
_diffrn_measured_fraction_theta_max 0.9986
_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    -10.27 349.73   1.50   10.00  72.69 -18.16  31.50    --   240
  2  \w    -76.17   6.33   1.50   10.00    --  -18.16  89.85 -32.66   55
  3  \w    -76.17   6.33   1.50   10.00    --  -18.16  89.85 171.34   55
  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  89.85 120.33   55
  6  \w   -122.88  22.62   1.50   10.00    --  -18.16 -59.25  20.08   97
  7  \w    -76.17   6.33   1.50   10.00    --  -18.16  89.85 -86.67   55
  8  \f   -349.73  10.27   1.50   10.00  31.11 -18.16 -31.50    --   240
;
_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      0.0379117000
_diffrn_orient_matrix_UB_12      0.0275351000
_diffrn_orient_matrix_UB_13      0.0622550000
_diffrn_orient_matrix_UB_21      -0.0796343000
_diffrn_orient_matrix_UB_22      0.0178764000
_diffrn_orient_matrix_UB_23      0.0104331000
_diffrn_orient_matrix_UB_31      -0.0371485000
_diffrn_orient_matrix_UB_32      -0.0591455000
_diffrn_orient_matrix_UB_33      0.0008307000
_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  0.1688
_diffrn_reflns_av_unetI/netI     0.1871
_diffrn_reflns_Laue_measured_fraction_full 0.9986
_diffrn_reflns_Laue_measured_fraction_max 0.9986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30267
_diffrn_reflns_point_group_measured_fraction_full 0.9986
_diffrn_reflns_point_group_measured_fraction_max 0.9986
_diffrn_reflns_theta_full        24.9954
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.81
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    7.918
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45263
_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 blue'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    2.157
_exptl_crystal_description       needle
_exptl_crystal_F_000             630.738
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.5031
_refine_diff_density_min         -1.7834
_refine_diff_density_rms         0.2888
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             11.2358
_refine_ls_goodness_of_fit_ref   1.0534
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0534
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0714
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0885P)^2^+2.3501P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_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              12
_reflns_limit_k_min              -14
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2388
_reflns_number_total             3582
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5dt00431d2.cif
_cod_data_source_block           MR_PC_3_BR_BLUE_autored
_cod_database_code               7719034
_reflns_odcompleteness_completeness 87.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.66
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 N3(H4), C14(H4a), C10(H6), C4(H7), C11(H13), C6(H14), C3(H17), C7(H1c),
 C18(H1e)
1.b Idealised Me refined as rotating group:
 C1(H15a,H15b,H15c)
;
_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 1.903
_oxdiff_exptl_absorpt_empirical_full_min 0.585