Formal asymmetric hydrobromination of styrenes via copper-catalyzed 1,3-halogen migration
Van Hoveln, R. J.; Schmid, S. C.; Tretbar, M.; Buttke, C. T.; Schomaker, J. M.; Chem. Sci. 5 (2014) 4763–; doi:10.1039/C4SC02040E

data_1517285
_publ_section_title
;
 Formal asymmetric hydrobromination of styrenes via copper-catalyzed
 1,3-halogen migration
;
_journal_issue                   12
_journal_name_full               'Chem. Sci.'
_journal_page_first              4763
_journal_paper_doi               10.1039/C4SC02040E
_journal_volume                  5
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_compound_source        'Schomaker Lab No. SCS2037'
_chemical_formula_moiety         'C19 H17 O4 S'
_chemical_formula_sum            'C19 H18 O4 S'
_chemical_formula_weight         342.39
_chemical_melting_point          ?
_chemical_name_systematic
4-methoxy-2-(1-(naphthalen-2-ylsulfonyl)ethyl)phenol
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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-2013
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.50660(10)
_cell_length_b                   14.1867(2)
_cell_length_c                   20.9510(4)
_cell_measurement_reflns_used    9799
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      72.2300
_cell_measurement_theta_min      4.2204
_cell_volume                     1636.70(5)
_computing_cell_refinement       'SAINT+ Ver. 8.30C (Bruker-AXS, 2013)'
_computing_data_collection       'APEX2 Ver. 2013.2-0 (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT+ Ver. 8.30C (Bruker-AXS, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997-2013)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997-2013)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997-2013)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1997-2013)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.001
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.60\% \w and 0.6\% \f scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'equatorially mounted graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25180
_diffrn_reflns_theta_full        72.26
_diffrn_reflns_theta_max         72.26
_diffrn_reflns_theta_min         3.76
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens, K FFCU 2K 90'
_exptl_absorpt_coefficient_mu    1.932
_exptl_absorpt_correction_T_max  0.8156
_exptl_absorpt_correction_T_min  0.3123
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method 'NMR sample was cooled to 7 \%C slowly'
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0504P)^2^+0.3524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0757
_reflns_number_gt                3155
_reflns_number_total             3198
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc02040e3.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

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

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1517285.cif.
;
_cod_database_code               1517285