Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade.
Gregory, Alex W.; Jakubec, Pavol; Turner, Paul; Dixon, Darren J.; Organic letters 15 (2013) 4330–4333; doi:10.1021/ol401784h

data_1512283
_publ_section_title
;
 Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective
 Hydroamination/N-Sulfonyliminium Cyclization Cascade.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4330
_journal_page_last               4333
_journal_paper_doi               10.1021/ol401784h
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H21 Br1 N2 O2 S1'
_chemical_formula_sum            'C21 H21 Br N2 O2 S'
_chemical_formula_weight         445.38
_chemical_melting_point          ?
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             12-12-18
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                90
_cell_angle_beta                 101.0903(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4507(1)
_cell_length_b                   16.2752(2)
_cell_length_c                   11.5043(1)
_cell_measurement_reflns_used    4512
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1920.19(3)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            35947
_diffrn_reflns_theta_full        27.481
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         5.103
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.269
_exptl_absorpt_correction_T_max  0.71
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.11
_refine_diff_density_min         -0.93
_refine_ls_abs_structure_details 'Flack (1983), 3898 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.010(4)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9896
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         8412
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.0005728
_refine_ls_shift/su_mean         0.0000319
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 1.16P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0635
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0635
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              19
_reflns_limit_k_min              -21
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                7894
_reflns_number_total             8412
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.35
_oxford_diffrn_Wilson_scale      5.35
_oxford_refine_ls_r_factor_ref   0.0325
_oxford_refine_ls_scale          0.4366(3)
_oxford_reflns_number_all        8412
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 021djd12
_cod_data_source_file            ol401784h_si_001.cif
_cod_data_source_block           15a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C21 H21 Br1 N2 O2 S1'
_cod_database_code               1512283
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) 
RIDE C   (  26,X'S) H   ( 262,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 272,X'S) H   ( 271,X'S) H   ( 273,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) H   ( 352,X'S) 
RIDE C   (  46,X'S) H   ( 462,X'S) H   ( 461,X'S) 
RIDE C   (  47,X'S) H   ( 472,X'S) H   ( 471,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) H   ( 482,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) H   ( 492,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) H   ( 502,X'S) H   ( 503,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;