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_7160275
_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
'C39 H24 B Cl F2 N5 O3 Re S2, 2(C H Cl3), 1[C6H14]'
_chemical_formula_sum            'C47 H40 B Cl7 F2 N5 O3 Re S2'
_chemical_formula_weight         1270.12
_chemical_name_systematic        'Re(I)-bis(benzothiazolyl) -3-pyrrolyl BODIPY'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-03
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-02 deposited with the CCDC.	2024-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                74.614(4)
_cell_angle_beta                 83.007(3)
_cell_angle_gamma                73.867(3)
_cell_formula_units_Z            2
_cell_length_a                   10.6474(3)
_cell_length_b                   13.6874(6)
_cell_length_c                   18.0722(7)
_cell_measurement_reflns_used    22875
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.1360
_cell_measurement_theta_min      1.6130
_cell_volume                     2436.08(17)
_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  '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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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   -349.73  10.27   1.80   10.00  31.11 -18.16 -31.50    --   200
  2  \w    -76.17   6.63   1.80   10.00    --  -18.16  89.85 120.33   46
  3  \w   -122.88  22.92   1.80   10.00    --  -18.16 -59.25  71.08   81
  4  \w    -76.17   6.63   1.80   10.00    --  -18.16  89.85 -32.66   46
  5  \w   -122.88  22.92   1.80   10.00    --  -18.16 -59.25-135.92   81
  6  \w    -76.17   6.63   1.80   10.00    --  -18.16  89.85-137.66   46
  7  \f    -10.27 349.73   1.80   10.00  72.69 -18.16  31.50    --   200
  8  \w    -76.17   6.63   1.80   10.00    --  -18.16  89.85  18.34   46
  9  \w    -76.17   6.63   1.80   10.00    --  -18.16  89.85 171.34   46
 10  \w   -122.88  22.92   1.80   10.00    --  -18.16 -59.25  20.08   81
;
_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      0.0145313000
_diffrn_orient_matrix_UB_12      0.0481528000
_diffrn_orient_matrix_UB_13      -0.0195888000
_diffrn_orient_matrix_UB_21      -0.0091304000
_diffrn_orient_matrix_UB_22      -0.0089611000
_diffrn_orient_matrix_UB_23      -0.0356357000
_diffrn_orient_matrix_UB_31      -0.0672876000
_diffrn_orient_matrix_UB_32      0.0263405000
_diffrn_orient_matrix_UB_33      0.0027871000
_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  0.0973
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            66595
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.597
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.020
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66405
_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 greenish green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_description       block
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.863
_refine_diff_density_min         -1.711
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         8552
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+2.9983P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7865
_reflns_number_total             8552
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01735h2.cif
_cod_data_source_block           mr_kcb_32_re_autored
_cod_depositor_comments
'Adding full bibliography for 7160273--7160275.cif.'
_cod_database_code               7160275
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.752
_shelx_estimated_absorpt_t_min   0.464
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H00L(0.031) H01M(0.041) H01P(0.044) H01K(0.04) H01J(0.038)
 H018(0.041) H01H(0.04) H01F(0.038) H017(0.031) H00R(0.031) H012(0.033)
 H01A(0.036) H00Y(0.033) H00W(0.03) H015(0.034) H00T(0.034) H00V(0.032)
 H01O(0.046) H01R(0.051) H01I(0.046) H019(0.04) H01B(0.087) H01C(0.087)
 H01D(0.087) H01N(0.045) H01S(0.064)
 Fixed X: H00L(0.168311) H01M(0.474188) H01P(0.694319) H01K(0.738284)
 H01J(0.409499) H018(0.20005) H01H(-0.006506) H01F(-0.135207) H017(-0.086351)
 H00R(0.153245) H012(0.04825) H01A(-0.149387) H00Y(-0.242934) H00W(0.349758)
 H015(0.38303) H00T(0.256674) H00V(0.078113) H01O(0.638517) H01R(0.784039)
 H01I(0.795975) H019(0.646316) H01B(0.855657) H01C(0.974114) H01D(0.931867)
 H01N(0.555017) H01S(0.55556)
 Fixed Y: H00L(0.729281) H01M(0.9235) H01P(0.944765) H01K(0.864888)
 H01J(0.667974) H018(0.634944) H01H(0.644394) H01F(0.624358) H017(0.633499)
 H00R(0.665839) H012(0.604229) H01A(0.559529) H00Y(0.570285) H00W(0.924989)
 H015(1.07959) H00T(1.168241) H00V(1.111563) H01O(0.896823) H01R(0.851732)
 H01I(0.546226) H019(0.59047) H01B(0.692389) H01C(0.696052) H01D(0.588922)
 H01N(0.486029) H01S(0.141696)
 Fixed Z: H00L(0.74386) H01M(0.645888) H01P(0.665244) H01K(0.805034)
 H01J(1.028498) H018(1.008984) H01H(0.948064) H01F(0.847618) H017(0.694728)
 H00R(0.347813) H012(0.269522) H01A(0.31227) H00Y(0.434161) H00W(0.469127)
 H015(0.482964) H00T(0.571376) H00V(0.641262) H01O(0.942294) H01R(1.040301)
 H01I(1.071803) H019(0.97648) H01B(1.172254) H01C(1.108792) H01D(1.144279)
 H01N(0.720807) H01S(0.719561)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 3.777
_oxdiff_exptl_absorpt_empirical_full_min 0.408