Synthesis, structure and spectroscopic properties of BODIPY dyes incorporating the pentafluorosulfanylphenyl group
James, Richard D.; Cucinotta, Fabio; Waddell, Paul G.; Benniston, Andrew C.; New Journal of Chemistry 47 (2023) 8451–8459; doi:10.1039/D3NJ00633F

data_7062399
_publ_section_title
;
 Synthesis, structure and spectroscopic properties of BODIPY dyes
 incorporating the pentafluorosulfanylphenyl group
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8451
_journal_page_last               8459
_journal_paper_doi               10.1039/D3NJ00633F
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C25 H18 B F7 N2 S'
_chemical_formula_sum            'C25 H18 B F7 N2 S'
_chemical_formula_weight         522.28
_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             2019-12-11
_audit_creation_method
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-02-08 deposited with the CCDC.	2023-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                97.069(3)
_cell_angle_beta                 94.791(3)
_cell_angle_gamma                102.348(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3305(3)
_cell_length_b                   9.7633(5)
_cell_length_c                   14.4959(5)
_cell_measurement_reflns_used    5015
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      66.7770
_cell_measurement_theta_min      4.6560
_cell_volume                     1135.61(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3968
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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     15.00 117.00   1.00    4.00    --   41.59  38.00-120.00  102
  2  \w     -3.00  96.00   1.00    4.00    --   41.59-125.00  30.00   99
  3  \w    -40.00  88.00   1.00    4.00    --   41.59 -19.00  60.00  128
  4  \w      9.00 133.00   1.00   16.00    --   93.50 -93.00 -36.75  124
  5  \w      4.00 178.00   1.00   16.00    --   93.50   0.00 -60.00  174
  6  \w      9.00 133.00   1.00   16.00    --   93.50 -93.00   6.33  124
  7  \w     16.00 124.00   1.00   16.00    --   93.50 -30.00 120.00  108
  8  \w      9.00  83.00   1.00   16.00    --   93.50 -94.00  60.00   74
  9  \w      9.00  83.00   1.00   16.00    --   93.50 -94.00-120.00   74
 10  \w     19.00 124.00   1.00   16.00    --   93.50 -61.00  90.00  105
 11  \w     19.00 121.00   1.00   16.00    --   93.50 -45.00 -60.00  102
 12  \w      9.00  83.00   1.00   16.00    --   93.50 -94.00 -90.00   74
 13  \w      9.00  83.00   1.00   16.00    --   93.50 -94.00 -60.00   74
 14  \w     16.00 124.00   1.00   16.00    --   93.50 -30.00  60.00  108
 15  \w      9.00 133.00   1.00   16.00    --   93.50 -93.00 -76.74  124
 16  \w      8.00 132.00   1.00   16.00    --   93.50 -91.00-148.51  124
 17  \w      9.00  83.00   1.00   16.00    --   93.50 -94.00  30.00   74
 18  \w     16.00 124.00   1.00   16.00    --   93.50 -30.00 -60.00  108
 19  \w     18.00 127.00   1.00   16.00    --   93.50 -77.00-120.00  109
 20  \w     17.00 123.00   1.00   16.00    --   93.50 -91.00  94.27  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1011711000
_diffrn_orient_matrix_UB_12      0.0584501000
_diffrn_orient_matrix_UB_13      0.0733752000
_diffrn_orient_matrix_UB_21      -0.0729084000
_diffrn_orient_matrix_UB_22      -0.1518579000
_diffrn_orient_matrix_UB_23      0.0181105000
_diffrn_orient_matrix_UB_31      0.1440595000
_diffrn_orient_matrix_UB_32      0.0131255000
_diffrn_orient_matrix_UB_33      0.0768470000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16081
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.897
_diffrn_reflns_theta_max         66.897
_diffrn_reflns_theta_min         4.686
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.955
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.42b (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_description       plate
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0438P)^2^+0.3177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0916
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3244
_reflns_number_total             4008
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj00633f2.cif
_cod_data_source_block           eag190007_fa
_cod_depositor_comments
'Adding full bibliography for 7062398--7062399.cif.'
_cod_original_cell_volume        1135.60(8)
_cod_database_code               7062399
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C25 H18 B1 F7 N2 S1'
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C26(H26), C25(H25), C15(H15), C7(H7), C18(H18), C1(H1), C2(H2),
 C17(H17), C6(H6), C23(H23), C22(H22)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              79523
_shelx_hkl_checksum              90548
_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 1.122
_oxdiff_exptl_absorpt_empirical_full_min 0.925