Synthesis and [3,3]-sigmatropic rearrangements of 5-(pentafluorosulfanyl)-pent-3-en-2-ol, its homologues, and trifluoromethyl analogues.
Dudziński, Piotr; Husstedt, Wibke S.; Matsnev, Andrej V.; Thrasher, Joseph S.; Haufe, Günter; Organic & biomolecular chemistry 19 (2021) 5607–5623; doi:10.1039/d1ob00870f

data_7158112
_publ_section_title
;
 Synthesis and [3,3]-sigmatropic rearrangements of
 5-(pentafluorosulfanyl)-pent-3-en-2-ol, its homologues, and
 trifluoromethyl analogues.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5607
_journal_page_last               5623
_journal_paper_doi               10.1039/d1ob00870f
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C10 H16 F5 N O4 S'
_chemical_formula_weight         341.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_Hall           'A 2 -2ab'
_space_group_name_H-M_alt        'A e a 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'APEX3 v2016.1-0'
_audit_update_record
;
2019-12-20 deposited with the CCDC.	2021-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.4208(12)
_cell_length_b                   26.557(2)
_cell_length_c                   8.6349(9)
_cell_measurement_reflns_used    2254
_cell_measurement_temperature    223.(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     3077.6(5)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection
;

Collect (Nonius B.V., 1998)
;
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      223.(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8284
_diffrn_reflns_theta_full        68.06
_diffrn_reflns_theta_max         68.06
_diffrn_reflns_theta_min         4.68
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Cu fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.537
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.280
_refine_ls_abs_structure_details
;

Flack x determined using 895 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.43(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         2543
_refine_ls_number_restraints     334
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0574
_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^)+(0.1016P)^2^+2.8370P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.1643
_reflns_number_gt                2274
_reflns_number_total             2543
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00870f2.cif
_cod_data_source_block           haf4760
_cod_depositor_comments          'Adding full bibliography for 7158112.cif.'
_cod_original_sg_symbol_H-M      'A b a 2'
_cod_database_code               7158112
_shelx_res_checksum              79438