One- and two-electron reductions of a bulky BODIPY compound
Pascoe, Liam M.; Lim, Li Feng; Kallmeier, Fabian; Cox, Nicholas; Brothers, Penelope Jane; Hicks, Jamie; Dalton Transactions  (2023) –; doi:10.1039/D3DT02048G

data_7713492
_publ_section_title
;
 One- and two-electron reductions of a bulky BODIPY compound
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT02048G
_journal_year                    2023
_chemical_formula_moiety         'C42 H49 B Br2 N2, C6 H14'
_chemical_formula_sum            'C48 H63 B Br2 N2'
_chemical_formula_weight         838.63
_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
_audit_creation_date             2023-06-27
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-06-29 deposited with the CCDC.	2023-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                81.880(2)
_cell_angle_beta                 73.939(2)
_cell_angle_gamma                89.774(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3900(3)
_cell_length_b                   14.6043(3)
_cell_length_c                   15.6325(4)
_cell_measurement_reflns_used    8953
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.3640
_cell_measurement_theta_min      5.2860
_cell_volume                     2255.08(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.968
_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      8.00 108.00   1.00    1.00    --   36.95  19.00 150.00  100
  2  \w     42.00  97.00   1.00    1.00    --   36.95  57.00   0.00   55
  3  \w     24.00  73.00   1.00    1.00    --   36.95 -99.00  90.00   49
  4  \w     21.00 101.00   1.00    1.00    --   36.95  57.00  60.00   80
  5  \w    -26.00  54.00   1.00    1.00    --   36.95 -57.00-180.00   80
  6  \w    -28.00  29.00   1.00    1.00    --   36.95 -57.00 -90.00   57
  7  \w     32.00  75.00   1.00    1.00    --   36.95 -99.00 -60.00   43
  8  \w      6.00  76.00   1.00    1.00    --   36.95 -99.00 150.00   70
  9  \w     42.00 127.00   1.00    4.00    --  111.00 -38.00 -30.00   85
 10  \w     43.00 128.00   1.00    4.00    --  111.00 -50.00 150.00   85
 11  \w     51.00 138.00   1.00    4.00    --  111.00 -77.00  30.00   87
 12  \w     44.00  71.00   1.00    4.00    --  111.00-111.00 -60.00   27
 13  \w     84.00 109.00   1.00    4.00    --  111.00-111.00 -60.00   25
 14  \w     44.00 106.00   1.00    4.00    --  111.00 -92.00-180.00   62
 15  \w     42.00 124.00   1.00    4.00    --  111.00 -38.00-120.00   82
 16  \w     56.00 108.00   1.00    4.00    --  111.00-111.00  30.00   52
 17  \w     84.00 109.00   1.00    4.00    --  111.00-111.00 150.00   25
 18  \w     55.00  81.00   1.00    4.00    --  111.00-111.00 150.00   26
 19  \w     95.00 144.00   1.00    4.00    --  111.00  50.00 120.00   49
 20  \w     63.00 125.00   1.00    4.00    --  111.00 -77.00-120.00   62
 21  \w    109.00 172.00   1.00    4.00    --  111.00  77.00 -60.00   63
 22  \w     44.00 177.00   1.00    4.00    --  111.00   0.00 -90.00  133
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15086
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.798
_diffrn_reflns_theta_min         3.944
_exptl_absorpt_coefficient_mu    2.514
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         8841
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+1.3460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0895
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7958
_reflns_number_total             8841
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt02048g2.cif
_cod_data_source_block           1-Br
_cod_original_cell_volume        2255.06(11)
_cod_database_code               7713492
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.844
_shelx_estimated_absorpt_t_min   0.660
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C44-C43 = C45-C44 = C46-C45 = C47-C46 = C48-C47
 1.53 with sigma of 0.008
 C44A-C43A = C45A-C44A = C46A-C45A = C47A-C46A = C48A-C47A
 1.53 with sigma of 0.008
 C43-C45 = C44-C46 = C45-C47 = C46-C48
 2.5 with sigma of 0.008
 C43A-C45A = C44A-C46A = C45A-C47A = C46A-C48A
 2.5 with sigma of 0.008
3. Uiso/Uaniso restraints and constraints
C48 \\sim C47 \\sim C46 \\sim C45 \\sim C44 \\sim C43: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01 within 2A
C48A \\sim C47A \\sim C46A \\sim C45A \\sim C44A \\sim C43A: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
Uanis(C41) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
4. Others
 Fixed Sof: C45(0.75) H45A(0.75) H45B(0.75) C46(0.75) H46A(0.75) H46B(0.75)
 C47(0.75) H47A(0.75) H47B(0.75) C44(0.75) H44A(0.75) H44B(0.75) C43(0.75)
 H43A(0.75) H43B(0.75) H43C(0.75) C48(0.75) H48A(0.75) H48B(0.75) H48C(0.75)
 C44A(0.25) H44C(0.25) H44D(0.25) C43A(0.25) H43D(0.25) H43E(0.25) H43F(0.25)
 C47A(0.25) H47C(0.25) H47D(0.25) C45A(0.25) H45C(0.25) H45D(0.25) C46A(0.25)
 H46C(0.25) H46D(0.25) C48A(0.25) H48D(0.25) H48E(0.25) H48F(0.25)
5.a Ternary CH refined with riding coordinates:
 C28(H28), C16(H16), C31(H31), C19(H19)
5.b Secondary CH2 refined with riding coordinates:
 C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C44(H44A,H44B), C44A(H44C,
 H44D), C47A(H47C,H47D), C45A(H45C,H45D), C46A(H46C,H46D)
5.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C2(H2), C3(H3), C12(H12), C38(H38), C24(H24), C26(H26),
 C25(H25), C13(H13), C36(H36), C14(H14)
5.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C21(H21A,H21B,H21C), C33(H33A,H33B,H33C), C30(H30A,H30B,
 H30C), C42(H42A,H42B,H42C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C18(H18A,
 H18B,H18C), C41(H41A,H41B,H41C), C40(H40A,H40B,H40C), C32(H32A,H32B,H32C),
 C43(H43A,H43B,H43C), C48(H48A,H48B,H48C), C43A(H43D,H43E,H43F), C48A(H48D,H48E,
 H48F)
;
_shelx_res_checksum              49752
_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
;