Synthesis, structure, and spectral and electrochemical properties of new visible to NIR absorbing 3-pyrrolyl BODIPY derivatives.
Behera, Kanhu Charan; Chauhan, Pinky; Tiwari, Shubham; Ravikanth, Mangalampalli; Organic & biomolecular chemistry 23 (2025) 935–947; doi:10.1039/d4ob01735h

data_7160274
_publ_section_title
;
 Synthesis, structure, and spectral and electrochemical properties of new
 visible to NIR absorbing 3-pyrrolyl BODIPY derivatives.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              935
_journal_page_last               947
_journal_paper_doi               10.1039/d4ob01735h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H18 B F2 N7'
_chemical_formula_sum            'C23 H18 B F2 N7'
_chemical_formula_weight         441.267
_chemical_name_systematic        '1,2,4-triazole -2-imine-3-pyrrolyl BODIPY'
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-25 deposited with the CCDC.	2024-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.006(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6585(4)
_cell_length_b                   10.0220(3)
_cell_length_c                   18.3087(5)
_cell_measurement_reflns_used    4763
_cell_measurement_temperature    151(3)
_cell_measurement_theta_max      25.0420
_cell_measurement_theta_min      1.8870
_cell_volume                     2084.34(11)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement
'olex2.refine 1.5-ac6-016 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      151(3)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9995
_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  22.92   1.80    5.00    --  -18.16 -59.25  20.08   81
  2  \f   -110.07  89.73   1.80    5.00  72.69 -18.16  31.50    --   111
  3  \w   -122.88  22.92   1.80    5.00    --  -18.16 -59.25  71.08   81
  4  \w   -122.88  22.92   1.80    5.00    --  -18.16 -59.25 173.08   81
  5  \f    158.27 350.87   1.80    5.00  31.11 -18.16 -31.50    --   107
;
_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      0.0365008000
_diffrn_orient_matrix_UB_12      0.0083540000
_diffrn_orient_matrix_UB_13      -0.0258488000
_diffrn_orient_matrix_UB_21      0.0153237000
_diffrn_orient_matrix_UB_22      0.0649395000
_diffrn_orient_matrix_UB_23      0.0143535000
_diffrn_orient_matrix_UB_31      0.0482635000
_diffrn_orient_matrix_UB_32      -0.0269175000
_diffrn_orient_matrix_UB_33      0.0265975000
_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  0.0902
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_Laue_measured_fraction_full 0.9995
_diffrn_reflns_Laue_measured_fraction_max 0.9995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37818
_diffrn_reflns_point_group_measured_fraction_full 0.9995
_diffrn_reflns_point_group_measured_fraction_max 0.9995
_diffrn_reflns_theta_full        24.9956
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.90
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48230
_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    1.406
_exptl_crystal_description       block
_exptl_crystal_F_000             912.649
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.2243
_refine_diff_density_min         -0.2731
_refine_diff_density_rms         0.0593
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             10.7391
_refine_ls_goodness_of_fit_ref   1.0183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3662
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0183
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1446
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -13
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              -9
_reflns_number_gt                2945
_reflns_number_total             3662
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob01735h2.cif
_cod_data_source_block           MR_KCB_42_autored
_cod_depositor_comments
'Adding full bibliography for 7160273--7160275.cif.'
_cod_database_code               7160274
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 N3(H006), C8(H00A), C11(H00F), C14(H00G), C22(H00J), C1(H00L), C21(H00M),
 C15(H00N), C12(H00O), C3(H00P), C7(H00Q), C2(H00R), C18(H00S), C16(H00T),
 C19(H00U)
1.b Idealised Me refined as rotating group:
 C23(H00b,H00c,H00d)
;
_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 1.693
_oxdiff_exptl_absorpt_empirical_full_min 0.598