Gold-Catalyzed Access to 1H-Isochromenes: Reaction Development and Mechanistic Insight
Tomás-Mendivil, Eder; Heinrich, Clément F.; Ortuno, Jean-Claude; Starck, Jérôme; Michelet, Véronique; ACS Catalysis 7 (2017) 380–; doi:10.1021/acscatal.6b02636

data_4514014
_publ_section_title
;
 Gold-Catalyzed Access to 1H-Isochromenes: Reaction Development and
 Mechanistic Insight
;
_journal_issue                   1
_journal_name_full               'ACS Catalysis'
_journal_page_first              380
_journal_paper_doi               10.1021/acscatal.6b02636
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C15 H12 Au Cl2 N O2, C H Cl3'
_chemical_formula_sum            'C16 H13 Au Cl5 N O2'
_chemical_formula_weight         625.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                76.336(2)
_cell_angle_beta                 87.282(2)
_cell_angle_gamma                65.557(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2785(5)
_cell_length_b                   8.9703(5)
_cell_length_c                   14.5673(8)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68
_cell_measurement_theta_min      3
_cell_volume                     955.40(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14931
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         68.327
_diffrn_reflns_theta_min         3.127
_diffrn_source                   'micro focus sealed tube'
_exptl_absorpt_coefficient_mu    21.002
_exptl_absorpt_correction_T_max  0.43
_exptl_absorpt_correction_T_min  0.28
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.149
_refine_diff_density_min         -0.917
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0581P)^2^+0.2722P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0773
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3303
_reflns_number_total             3397
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b02636_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4514014
_shelx_shelxl_version_number     2014/7
_exptl_absorpt_special_details
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;
_shelx_res_checksum              53468
_shelx_hkl_checksum              97501