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_1512282
_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         'C16 H17 Br N2 O, C H Cl3'
_chemical_formula_sum            'C17 H18 Br Cl3 N2 O'
_chemical_formula_weight         452.60
_chemical_melting_point          ?
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2013-05-09
_audit_creation_method           CRYSTALS_ver_14.52
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0236(2)
_cell_length_b                   12.9544(2)
_cell_length_c                   13.4366(2)
_cell_measurement_reflns_used    83413
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1918.80(5)
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.087
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            56832
_diffrn_reflns_theta_full        26.925
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         5.159
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.567
_exptl_absorpt_correction_T_max  0.46
_exptl_absorpt_correction_T_min  0.17
_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    1.567
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.44
_refine_ls_abs_structure_details 'Flack (1983), 1893 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.007(8)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4361
_refine_ls_number_restraints     162
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.0020766
_refine_ls_shift/su_mean         0.0001238
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 69.2 115. 71.6 31.4 7.79 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0832
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0832
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                4092
_reflns_number_total             4361
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.71
_oxford_diffrn_Wilson_scale      3.06
_oxford_refine_ls_r_factor_ref   0.0374
_oxford_refine_ls_scale          0.6515(14)
_oxford_reflns_number_all        4361
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 015DJD12
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
EQUIV PART(1001,OCC) PART(1002,OCC) 
WEIGHT -1 PART(1002,OCC) 
RIDE N   (   4,X'S) H   (  41,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) H   ( 153,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
SAME  C(21)  CL(22)  CL(23)  CL(24)  AND 
CONT  C(21)  CL(23)  CL(24)  CL(22)  AND 
CONT  C(21)  CL(24)  CL(22)  CL(23)  AND 
CONT  C(25)  CL(26)  CL(27)  CL(28)  AND 
CONT  C(25)  CL(27)  CL(28)  CL(26)  AND 
CONT  C(25)  CL(28)  CL(26)  CL(27) 
SIMU  0.01   C(21)  CL(22)  CL(23)  CL(24)  AND 
CONT  C(21)  CL(23)  CL(24)  CL(22)  AND 
CONT  C(21)  CL(24)  CL(22)  CL(23)  AND 
CONT  C(25)  CL(26)  CL(27)  CL(28)  AND 
CONT  C(25)  CL(27)  CL(28)  CL(26)  AND 
CONT  C(25)  CL(28)  CL(26)  CL(27) 
DELU  0.01   C(21)  CL(22)  CL(23)  CL(24)  AND 
CONT  C(21)  CL(23)  CL(24)  CL(22)  AND 
CONT  C(21)  CL(24)  CL(22)  CL(23)  AND 
CONT  C(25)  CL(26)  CL(27)  CL(28)  AND 
CONT  C(25)  CL(27)  CL(28)  CL(26)  AND 
CONT  C(25)  CL(28)  CL(26)  CL(27) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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_cod_data_source_file            ol401784h_si_001.cif
_cod_data_source_block           10b
_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.

'_atom_sites_solution_primary'
value 'Other' changed to 'other' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

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_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C17 H18 Br1 Cl3 N2 O1'
_cod_database_code               1512282