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_1568074
_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_absolute_configuration ad
_chemical_formula_moiety         'C48 H16 F16 S8, 3[C6H14]'
_chemical_formula_sum            'C66 H58 F16 S8'
_chemical_formula_weight         1411.60
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-05-26 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   34.3683(7)
_cell_length_b                   28.4432(5)
_cell_length_c                   5.44470(10)
_cell_measurement_reflns_used    9010
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.038426364171805
_cell_measurement_theta_min      0.8971284506740053
_cell_volume                     5322.44(17)
_computing_data_collection       'GDA - generic data acquisition software'
_computing_data_reduction
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 3.3.3-g5efb02d60-release (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 3.3.3 (Winter, G., 2010)
;
_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      'N2 gas'
_diffrn_ambient_temperature      100(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_type            'Dectris PILATUS 2M'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Fixed \c 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            42986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        20.147
_diffrn_reflns_theta_max         20.147
_diffrn_reflns_theta_min         0.901
_diffrn_source                   Synchrotron
_diffrn_source_details           'Allan et al. (2017)'
_diffrn_source_type              'Diamond Light Source Beamline I19-1'
_exptl_absorpt_coefficient_mu    0.408
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_description       needle
_exptl_crystal_F_000             2904
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane, hexane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1475 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         5593
_refine_ls_number_restraints     1893
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1390P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1794
_refine_ls_wR_factor_ref         0.1926
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4168
_reflns_number_total             5593
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05348a4.cif
_cod_data_source_block           1a-Hexane
_cod_depositor_comments
'Adding full bibliography for 1568074--1568079.cif.'
_cod_database_code               1568074
_nottingham_internal_coll_name   OATSWB
_nottingham_internal_coll_number 18923
_nottingham_internal_coll_client AT/SW
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'fine \w scans'
_nottingham_internal_coll_frame_time 0.2
_nottingham_internal_coll_frame_width 0.01
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   04/03/2021
_nottingham_internal_coll_location DLS
_nottingham_internal_coll_instrument i19-EH1
_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
_nottingham_internal_archive_date 13/05/2021
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 S8-C14 \\sim S8-C21 \\sim S7-C24 \\sim S7-C31 \\sim S6-C34 \\sim S6-C41 \\sim
S5-C44 \\sim S5-C51 \\sim S4-
 C54 \\sim S4-C61 \\sim S3-C64 \\sim S3-C71 \\sim S2-C74 \\sim S2-C81 \\sim
S1-C84 \\sim S1-C11
 with sigma of 0.02
 F30-C26 \\sim F29-C25 \\sim F27-C22 \\sim F28-C23 \\sim F47-C42 \\sim F48-C43
\\sim F50-C46 \\sim F49-C45
 \\sim F67-C62 \\sim F68-C63 \\sim F69-C65 \\sim F70-C66 \\sim F87-C82 \\sim
F88-C83 \\sim F89-C85 \\sim F90-C86
 with sigma of 0.02
3. Restrained planarity
 C21, C22, C23, C24, C25, C26, F27, F28, F29, F30
 with sigma of 0.1
 C81, C82, C83, C84, C85, C86, F87, F88, F89, F90
 with sigma of 0.1
 C61, C62, C63, C64, C65, C66, F67, F68, F69, F70
 with sigma of 0.1
 C41, C42, C43, C44, C45, C46, F47, F48, F49, F50
 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} sigma for 1-2: 0.02, 1-3: 0.04
{C14, C15, C16, C11, C12, C13} sigma for 1-2: 0.02, 1-3: 0.04
{C14, C13, C12, C11, C16, C15} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C11, C12, C13, C14, C15, C16}
{C21, C26, C25, C24, C23, C22} sigma for 1-2: 0.02, 1-3: 0.04
{C24, C25, C26, C21, C22, C23} sigma for 1-2: 0.02, 1-3: 0.04
{C24, C23, C22, C21, C26, C25} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C21, C22, C23, C24, C25, C26}
{C11, C12, C13, C14, C15, C16} sigma for 1-2: 0.02, 1-3: 0.04
{C11, C16, C15, C14, C13, C12} sigma for 1-2: 0.02, 1-3: 0.04
{C14, C15, C16, C11, C12, C13} sigma for 1-2: 0.02, 1-3: 0.04
{C14, C13, C12, C11, C16, C15} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C31, C32, C33, C34, C35, C36}
{C21, C22, C23, C24, C25, C26} sigma for 1-2: 0.02, 1-3: 0.04
{C21, C26, C25, C24, C23, C22} sigma for 1-2: 0.02, 1-3: 0.04
{C24, C25, C26, C21, C22, C23} sigma for 1-2: 0.02, 1-3: 0.04
{C24, C23, C22, C21, C26, C25} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C41, C42, C43, C44, C45, C46}
{C11, C12, C13, C14, C15, C16} sigma for 1-2: 0.02, 1-3: 0.04
{C11, C16, C15, C14, C13, C12} sigma for 1-2: 0.02, 1-3: 0.04
{C14, C15, C16, C11, C12, C13} sigma for 1-2: 0.02, 1-3: 0.04
{C14, C13, C12, C11, C16, C15} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C51, C52, C53, C54, C55, C56}
{C21, C22, C23, C24, C25, C26} sigma for 1-2: 0.02, 1-3: 0.04
{C21, C26, C25, C24, C23, C22} sigma for 1-2: 0.02, 1-3: 0.04
{C24, C25, C26, C21, C22, C23} sigma for 1-2: 0.02, 1-3: 0.04
{C24, C23, C22, C21, C26, C25} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C61, C62, C63, C64, C65, C66}
{C11, C12, C13, C14, C15, C16} sigma for 1-2: 0.02, 1-3: 0.04
{C11, C16, C15, C14, C13, C12} sigma for 1-2: 0.02, 1-3: 0.04
{C14, C15, C16, C11, C12, C13} sigma for 1-2: 0.02, 1-3: 0.04
{C14, C13, C12, C11, C16, C15} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C71, C72, C73, C74, C75, C76}
{C21, C22, C23, C24, C25, C26} sigma for 1-2: 0.02, 1-3: 0.04
{C21, C26, C25, C24, C23, C22} sigma for 1-2: 0.02, 1-3: 0.04
{C24, C25, C26, C21, C22, C23} sigma for 1-2: 0.02, 1-3: 0.04
{C24, C23, C22, C21, C26, C25} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C81, C82, C83, C84, C85, C86}
7.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C32(H32), C33(H33), C35(H35),
 C36(H36), C52(H52), C53(H53), C55(H55), C56(H56), C72(H72), C73(H73), C75(H75),
  C76(H76)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              52798
_shelx_fab_checksum              79866
_olex2_submission_special_instructions 'No special instructions were received'