Mechanistic, crystallographic, and computational studies on the catalytic, enantioselective sulfenofunctionalization of alkenes
Scott E. Denmark; Eduard Hartmann; David J. P. Kornfilt; Hao Wang; Nature Chemistry 6 (2014) 1056–1064; doi:10.1038/nchem.2109

data_1551400
_publ_section_title
;
 Mechanistic, crystallographic, and computational studies on the
 catalytic, enantioselective sulfenofunctionalization of alkenes
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              1056
_journal_page_last               1064
_journal_paper_doi               10.1038/nchem.2109
_journal_volume                  6
_journal_year                    2014
_chemical_formula_moiety
; 
C32 H12 B F24, C34 H37 N3 P S2, 2(C H2 Cl2) 
;
_chemical_formula_sum            'C68 H53 B Cl4 F24 N3 P S2'
_chemical_formula_weight         1615.83
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                76.883(2)
_cell_angle_beta                 70.416(2)
_cell_angle_gamma                65.366(2)
_cell_formula_units_Z            2
_cell_length_a                   14.370(2)
_cell_length_b                   15.135(2)
_cell_length_c                   19.376(3)
_cell_measurement_reflns_used    7590
_cell_measurement_temperature    167(2)
_cell_measurement_theta_max      23.60
_cell_measurement_theta_min      2.21
_cell_volume                     3590.2(9)
_computing_cell_refinement       'SAINT V7.68A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2010.11-3 (Bruker, 2010)'
_computing_data_reduction
; 
SAINT V7.68A, XPREP V2005/2, SADABS V2008/2, TWINABS V2008/2 
(Bruker, 2005 & 2008) 
;
_computing_molecular_graphics
; 
SHELXTL V6.12 (Bruker, 2005), CrystalMaker v2.1.3 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      167(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Siemens Platform/ApexII CCD'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  bm32zas
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            42822
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.12
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_T_max  0.9985
_exptl_absorpt_correction_T_min  0.9152
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1636
_exptl_crystal_id                bm32zas
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (2 2 3) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.542
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.396
_refine_diff_density_max         0.889
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1132
_refine_ls_number_reflns         14547
_refine_ls_number_restraints     1164
_refine_ls_restrained_S_all      1.333
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0746
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1202P)^2^+4.2008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2062
_refine_ls_wR_factor_ref         0.2315
_reflns_number_gt                9769
_reflns_number_total             14547
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nchem.2109-s2.cif
_cod_data_source_block           bm32zas
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_Hall     ' -P 1'
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               1551400