Enantioselective bromocycloetherification by Lewis base/chiral Brønsted acid cooperative catalysis.
Denmark, Scott E.; Burk, Matthew T.; Organic letters 14 (2012) 256–259; doi:10.1021/ol203033k

data_1503528
_publ_contact_author
; 
Danielle L. Gray 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_section_title
;
 Enantioselective bromocycloetherification by Lewis base/chiral Br\/onsted
 acid cooperative catalysis.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              256
_journal_page_last               259
_journal_paper_doi               10.1021/ol203033k
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C16 H15 N O '
_chemical_formula_sum            'C16 H15 N O'
_chemical_formula_weight         237.29
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
? 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0812(4)
_cell_length_b                   13.6176(8)
_cell_length_c                   15.5864(9)
_cell_measurement_reflns_used    4952
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      67.35
_cell_measurement_theta_min      4.31
_cell_volume                     1290.73(14)
_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 0.976
_diffrn_measured_fraction_theta_max 0.976
_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  bc87pas
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8015
_diffrn_reflns_theta_full        68.36
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_min         4.31
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  0.9405
_exptl_absorpt_correction_T_min  0.8605
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_id                bc87pas
_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 1 3) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.406
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
; 
 Flack H D (1983), Acta Cryst. A39, 876-881. 
 Hooft, Straver & Spek. J. Appl. Cryst. (2008), 41, 96-103. 
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.0058(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0447P)^2^+0.1264P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0838
_reflns_number_gt                2146
_reflns_number_total             2229
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol203033k_si_002.cif
_cod_data_source_block           bc87pas
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               1503528
_refine_ls_abs_structure_hooft   0.12(14)