Catalysis enabled synthesis, structures, and reactivities of fluorinated S<sub>8</sub>-corona[<i>n</i>]arenes (<i>n</i> = 8-12).
Turley, Andrew T.; Hanson-Heine, Magnus W D; Argent, Stephen P.; Hu, Yaoyang; Jones, Thomas A.; Fay, Michael; Woodward, Simon; Chemical science 14 (2022) 70–77; doi:10.1039/d2sc05348a

data_1568078
_publ_section_title
;
 Catalysis enabled synthesis, structures, and reactivities of fluorinated
 S<sub>8</sub>-corona[<i>n</i>]arenes (<i>n</i> = 8-12).
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              70
_journal_page_last               77
_journal_paper_doi               10.1039/d2sc05348a
_journal_volume                  14
_journal_year                    2022
_chemical_formula_moiety         'C48 H16 F16 S8, C H Cl3'
_chemical_formula_sum            'C49 H17 Cl3 F16 S8'
_chemical_formula_weight         1272.45
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-05-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-05-26 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                78.57(2)
_cell_angle_beta                 81.39(2)
_cell_angle_gamma                82.79(2)
_cell_formula_units_Z            1
_cell_length_a                   6.7916(16)
_cell_length_b                   13.818(4)
_cell_length_c                   15.064(4)
_cell_measurement_reflns_used    1379
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      44.2960
_cell_measurement_theta_min      3.9770
_cell_volume                     1363.3(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'PILATUS3 R 200K Hybrid Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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     12.00 122.00   0.50   30.00    --   34.70  52.00  26.76  220
  2  \w     13.00 108.00   0.50   30.00    --   34.70  69.00 -56.93  190
  3  \w      8.00  53.00   0.50   30.00    --   34.70  71.00 124.05   90
  4  \w     -2.00  56.00   0.50   30.00    --   34.70 -82.00 -60.00  116
  5  \w    -16.00  56.00   0.50   30.00    --   34.70 -82.00-150.00  144
  6  \w     -1.00  68.00   0.50   30.00    --   34.70 -82.00  30.00  138
  7  \w    -25.00  67.00   0.50   30.00    --   34.70 -82.00 150.00  184
  8  \w      4.00  68.00   0.50   30.00    --   34.70 -82.00  60.00  128
  9  \w    -17.00  63.00   0.50   30.00    --   34.70 -77.00   0.00  160
 10  \w     15.00 110.00   0.50   30.00    --   34.70  38.00-120.00  190
 11  \w    -42.00  49.00   0.50   30.00    --   34.70 -77.00 120.00  182
 12  \w    -22.00  68.00   0.50   30.00    --   34.70 -82.00-120.00  180
 13  \w     12.00  99.00   0.50   30.00    --   34.70  38.00 150.00  174
 14  \w    -46.00  47.00   0.50   30.00    --   34.70 -57.00 -60.00  186
 15  \w      9.00  66.00   0.50   30.00    --   34.70  68.00  47.54  114
 16  \w      9.00  98.00   0.50   30.00    --   34.70  69.00 142.03  178
 17  \w      8.00  46.00   0.50   30.00    --   34.70  72.00 -17.44   76
 18  \w     90.00 121.00   0.50   30.00    --   34.70  72.00 -17.44   62
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'XtalLAB PRO MM007, PILATUS3 R 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0188819000
_diffrn_orient_matrix_UB_12      -0.0136573000
_diffrn_orient_matrix_UB_13      -0.1000707000
_diffrn_orient_matrix_UB_21      0.0029754000
_diffrn_orient_matrix_UB_22      -0.1131501000
_diffrn_orient_matrix_UB_23      0.0319655000
_diffrn_orient_matrix_UB_31      -0.2297537000
_diffrn_orient_matrix_UB_32      0.0087609000
_diffrn_orient_matrix_UB_33      0.0057373000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1341
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5179
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        34.815
_diffrn_reflns_theta_max         34.815
_diffrn_reflns_theta_min         4.031
_diffrn_source                   'rotating anode'
_diffrn_source_type              'MicroMax 007 HF'
_exptl_absorpt_coefficient_mu    5.198
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.574
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_description       needle
_exptl_crystal_F_000             634
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.287
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         1148
_refine_ls_number_restraints     1164
_refine_ls_restrained_S_all      1.608
_refine_ls_R_factor_all          0.2063
_refine_ls_R_factor_gt           0.1755
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4535
_refine_ls_wR_factor_ref         0.4768
_reflns_Friedel_coverage         0.000
_reflns_number_gt                812
_reflns_number_total             1148
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05348a4.cif
_cod_data_source_block           1a-CHCl3
_cod_depositor_comments
'Adding full bibliography for 1568074--1568079.cif.'
_cod_original_cell_volume        1363.3(7)
_cod_database_code               1568078
_nottingham_internal_coll_name   OATSWC
_nottingham_internal_coll_number 18979
_nottingham_internal_coll_client AT/SW
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time 30.00
_nottingham_internal_coll_frame_width 0.50
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   16/03/2021
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'XtalLAB PRO, A00000876'
_nottingham_internal_process_date 12/05/2021
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 12/05/2021
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 13/05/2021
_nottingham_internal_refinement_user pczspa
_nottingham_internal_validation_date 13/05/2021
_nottingham_internal_validation_user pczspa
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C48H16F16S8
_chemical_oxdiff_usercomment     'OATSWC #18979 MM-755 AT/SW Fomblin micromount'
_shelx_estimated_absorpt_t_max   0.864
_shelx_estimated_absorpt_t_min   0.257
_reflns_odcompleteness_completeness 96.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     44.45
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C1S-Cl4S = C1S-Cl2S = C1S-Cl3S
 1.78 with sigma of 0.02
 Cl2S-Cl3S \\sim Cl3S-Cl4S \\sim Cl4S-Cl2S
 with sigma of 0.02
 S1-C11 \\sim S1_$1-C44 \\sim S2-C14 \\sim S2-C21 \\sim S3-C24 \\sim S3-C31
\\sim S4-C34 \\sim S4-C41 \\sim S1-
 C44_$1 \\sim S1-C11 \\sim S2-C14 \\sim S2-C21 \\sim S3-C24 \\sim S3-C31 \\sim
S4-C34 \\sim S4-C41
 with sigma of 0.02
 S1-C12 \\sim S1-C16 \\sim S2-C22 \\sim S2-C26 \\sim S2-C13 \\sim S2-C15 \\sim
S3-C23 \\sim S3-C25 \\sim S3-
 C32 \\sim S3-C36 \\sim S4-C33 \\sim S4-C35 \\sim S4-C42 \\sim S4-C46 \\sim
S1-C45_$1 \\sim S1-C43_$1
 with sigma of 0.02
3. Restrained planarity
 C41, C42, C43, C44, C45, C46, F47, F48, F49, F50
 with sigma of 0.1
 C21, C22, C23, C24, C25, C26, F27, F28, F29, F30
 with sigma of 0.1
 C11, C12, C13, C14, C15, C16, F17, F18, F19, F20
 with sigma of 0.1
 C31, C32, C33, C34, C35, C36, F37, F38, F39, F40
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{C11, C16, C15, C14, C13, C12, F20, F19, F18, F17} sigma for 1-2: 0.02, 1-3:
0.04
as in
{C11, C12, C13, C14, C15, C16, F17, F18, F19, F20}
{C11, C16, C15, C14, C13, C12, F20, F19, F18, F17} sigma for 1-2: 0.02, 1-3:
0.04
{C11, C12, C13, C14, C15, C16, F17, F18, F19, F20} sigma for 1-2: 0.02, 1-3:
0.04
as in
{C21, C22, C23, C24, C25, C26, F27, F28, F29, F30}
{C11, C12, C13, C14, C15, C16, F17, F18, F19, F20} sigma for 1-2: 0.02, 1-3:
0.04
{C11, C16, C15, C14, C13, C12, F20, F19, F18, F17} sigma for 1-2: 0.02, 1-3:
0.04
as in
{C31, C32, C33, C34, C35, C36, F37, F38, F39, F40}
{C11, C12, C13, C14, C15, C16, F17, F18, F19, F20} sigma for 1-2: 0.02, 1-3:
0.04
{C11, C16, C15, C14, C13, C12, F20, F19, F18, F17} sigma for 1-2: 0.02, 1-3:
0.04
as in
{C41, C42, C43, C44, C45, C46, F47, F48, F49, F50}
7. Others
 Fixed Sof: H12(0.5) H13(0.5) H15(0.5) H16(0.5) F17(0.5) F18(0.5) F19(0.5)
 F20(0.5) H22(0.5) H23(0.5) H25(0.5) H26(0.5) F27(0.5) F28(0.5) F29(0.5)
 F30(0.5) H32(0.5) H33(0.5) H35(0.5) H36(0.5) F37(0.5) F38(0.5) F39(0.5)
 F40(0.5) H42(0.5) H43(0.5) H45(0.5) H46(0.5) F47(0.5) F48(0.5) F49(0.5)
 F50(0.5) C1S(0.5) H1S(0.5) Cl2S(0.5) Cl3S(0.5) Cl4S(0.5)
8.a Ternary CH refined with riding coordinates:
 C1S(H1S)
8.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C22(H22), C23(H23), C25(H25),
 C26(H26), C32(H32), C33(H33), C35(H35), C36(H36), C42(H42), C43(H43), C45(H45),
  C46(H46)
;
_shelx_res_checksum              2669
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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 7.835
_oxdiff_exptl_absorpt_empirical_full_min 0.367