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_1551401
_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
; 
C56 H60 N6 P2 Se2, 2(Cl6 Sb), C6H6, C4H10O2 
;
_chemical_formula_sum            'C66 H76 Cl12 N6 O2 P2 Sb2 Se2'
_chemical_formula_weight         1874.09
_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                67.081(2)
_cell_angle_beta                 73.258(2)
_cell_angle_gamma                88.706(2)
_cell_formula_units_Z            1
_cell_length_a                   12.0050(6)
_cell_length_b                   12.2783(6)
_cell_length_c                   14.5779(7)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      67.54
_cell_measurement_theta_min      3.45
_cell_volume                     1885.47(16)
_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 V2007/4, TWINABS V2007/5 
(Bruker, 2005 & 2007) 
;
_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      193(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device       'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_wavelength_id  bc11tasq
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23671
_diffrn_reflns_theta_full        67.82
_diffrn_reflns_theta_max         67.82
_diffrn_reflns_theta_min         3.45
_exptl_absorpt_coefficient_mu    11.470
_exptl_absorpt_correction_T_max  0.3726
_exptl_absorpt_correction_T_min  0.1241
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             934
_exptl_crystal_id                bc11tasq
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (1 -3 -3) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.172
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     556
_refine_ls_number_reflns         6453
_refine_ls_number_restraints     499
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.3034P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0816
_reflns_number_gt                6054
_reflns_number_total             6453
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nchem.2109-s3.cif
_cod_data_source_block           bc11tasq
_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_H-M      'P-1   '
_cod_database_code               1551401