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_7062398
_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         'C17 H14 B F7 N2 S'
_chemical_formula_sum            'C17 H14 B F7 N2 S'
_chemical_formula_weight         422.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-19
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.6584(3)
_cell_length_b                   8.0294(3)
_cell_length_c                   36.9894(11)
_cell_measurement_reflns_used    3313
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      66.9230
_cell_measurement_theta_min      4.4430
_cell_volume                     3462.58(19)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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     73.00 118.00   1.00   10.00    --   39.25 125.00   0.00   45
  2  \w    -40.00  71.00   1.00   10.00    --   39.25 -38.00  30.00  111
  3  \w     73.00 118.00   1.00   10.00    --   39.25 125.00 -30.00   45
  4  \w     63.00 175.00   1.00   40.00    --   96.50  61.00 -90.00  112
  5  \w     15.00  90.00   1.00   40.00    --   96.50-111.00   0.00   75
  6  \w     15.00  90.00   1.00   40.00    --   96.50-111.00-180.00   75
  7  \w     79.00 173.00   1.00   40.00    --   96.50 111.00-150.00   94
  8  \w     86.00 165.00   1.00   40.00    --   96.50  45.00  90.00   79
  9  \w     29.00  55.00   1.00   40.00    --   96.50 -94.00   0.00   26
 10  \w     40.00  90.00   1.00   40.00    --   96.50-111.00  30.00   50
;
_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      0.1166085000
_diffrn_orient_matrix_UB_12      -0.0858517000
_diffrn_orient_matrix_UB_13      0.0060518000
_diffrn_orient_matrix_UB_21      -0.0447923000
_diffrn_orient_matrix_UB_22      -0.0747531000
_diffrn_orient_matrix_UB_23      0.0356575000
_diffrn_orient_matrix_UB_31      -0.0431745000
_diffrn_orient_matrix_UB_32      -0.1545600000
_diffrn_orient_matrix_UB_33      -0.0206048000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            13046
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.158
_diffrn_reflns_theta_max         67.158
_diffrn_reflns_theta_min         4.483
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.398
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.638
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_description       prism
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.00035(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0455P)^2^+1.8257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2498
_reflns_number_total             3083
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj00633f2.cif
_cod_data_source_block           eag190006_fa
_cod_depositor_comments
'Adding full bibliography for 7062398--7062399.cif.'
_cod_original_cell_volume        3462.60(18)
_cod_database_code               7062398
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C17 H14 B1 F7 N2 S1'
_reflns_odcompleteness_completeness 99.92
_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:
 C1(H1), C2(H2), C6(H6), C7(H7), C14(H14), C15(H15), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              61667
_shelx_hkl_checksum              78697
_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 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.841