Gold-Mediated Synthesis and Functionalization of Chiral Halopyridones
Khanh Hung Nguyen; Sophie Tomasi; Myriam Le Roch; Loïc Toupet; Jacques Renault; Philippe Uriac; Nicolas Gouault; Journal of Organic Chemistry 78 (2013) 7809–7815; doi:10.1021/jo400827b

data_4028484
_publ_section_title
;
 Gold-Mediated Synthesis and Functionalization of Chiral Halopyridones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7809
_journal_page_last               7815
_journal_paper_doi               10.1021/jo400827b
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H24 Br N O3'
_chemical_formula_weight         442.34
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6670(2)
_cell_length_b                   11.1719(2)
_cell_length_c                   19.3587(4)
_cell_measurement_reflns_used    13961
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      2.78
_cell_volume                     2090.72(7)
_computing_cell_refinement
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.35.11'
_computing_data_collection
'CrysAlis CCD, Oxford Diffraction Ltd.,Version 1.171.35.11'
_computing_data_reduction
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.35.11'
_computing_molecular_graphics    'MERCURY 2.4.5(CCDC, 2011)'
_computing_publication_material  'WINGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97_(Altomare & al., 1999)'
_diffrn_ambient_temperature      140(2)
_diffrn_detector_area_resol_mean 16.1852
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD Saphire 3 Xcalibur'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31686
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    1.989
_exptl_absorpt_correction_T_max  0.76257
_exptl_absorpt_correction_T_min  0.62451
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'Alcock(1970) crystallographic computing,p271'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.014(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.826
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.826
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0274
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0239P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0461
_refine_ls_wR_factor_ref         0.0473
_reflns_number_gt                3737
_reflns_number_total             4562
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400827b_si_001.cif
_cod_data_source_block           h224
_cod_database_code               4028484