Can acyclic conformational control be achieved via a sulfur–fluorine gauche effect?
Thiehoff, C.; Holland, M. C.; Daniliuc, C.; Houk, K. N.; Gilmour, R.; Chem. Sci. 6 (2015) 3565–; doi:10.1039/C5SC00871A

data_1519421
_publ_section_title
;
 Can acyclic conformational control be achieved via a sulfur--fluorine
 gauche effect?
;
_journal_issue                   6
_journal_name_full               'Chem. Sci.'
_journal_page_first              3565
_journal_paper_doi               10.1039/C5SC00871A
_journal_volume                  6
_journal_year                    2015
_chemical_formula_sum            'C8 H8 F N O3 S'
_chemical_formula_weight         217.21
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-06 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.3421(7)
_cell_length_b                   4.6595(2)
_cell_length_c                   9.8133(4)
_cell_measurement_reflns_used    1685
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      4.08
_cell_volume                     930.14(6)
_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 (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7714
_diffrn_reflns_theta_full        25.57
_diffrn_reflns_theta_max         25.57
_diffrn_reflns_theta_min         4.49
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.8472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         1589
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0533P)^2^+1.1342P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1530
_reflns_number_gt                1195
_reflns_number_total             1589
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5sc00871a2.cif
_cod_data_source_block           gil7899
_cod_depositor_comments
'Adding full bibliography for 1519418--1519422.cif.'
_cod_original_sg_symbol_H-M      Pna21
_cod_database_code               1519421