Anti-Selective Aldol Reactions of Pentafluorosulfanylacetic Acid Esters with Aldehydes Mediated by Dicyclohexylchloroborane.
Friese, Florian W.; Dreier, Anna-Lena; Matsnev, Andrej V.; Daniliuc, Constantin G.; Thrasher, Joseph S.; Haufe, Günter; Organic letters 18 (2016) 1012–; doi:10.1021/acs.orglett.6b00136

data_1542703
_publ_section_title
;
 Anti-Selective Aldol Reactions of Pentafluorosulfanylacetic Acid Esters
 with Aldehydes Mediated by Dicyclohexylchloroborane.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1012
_journal_paper_doi               10.1021/acs.orglett.6b00136
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C16 H15 F5 O3 S'
_chemical_formula_weight         382.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                85.184(5)
_cell_angle_beta                 83.294(5)
_cell_angle_gamma                87.881(5)
_cell_formula_units_Z            2
_cell_length_a                   5.5840(4)
_cell_length_b                   11.7071(9)
_cell_length_c                   12.0947(9)
_cell_measurement_reflns_used    5304
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.6522
_cell_measurement_theta_min      3.6917
_cell_volume                     782.18(10)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1382
_diffrn_reflns_av_unetI/netI     0.0848
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15047
_diffrn_reflns_theta_full        65.07
_diffrn_reflns_theta_max         65.07
_diffrn_reflns_theta_min         3.69
_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    2.511
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.447
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0769
_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^)+(0.0613P)^2^+2.1893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.1793
_reflns_number_gt                1833
_reflns_number_total             2631
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00136_si_002.cif
_cod_data_source_block           haf8005
_cod_database_code               1542703
_shelx_res_checksum              21112
_shelx_hkl_checksum              93971