Synthesis of Functionalized 1H-Isochromene Derivatives via a Au-Catalyzed Domino Cycloisomerization/Reduction Approach.
Tomás-Mendivil, Eder; Starck, Jérôme; Ortuno, Jean-Claude; Michelet, Véronique; Organic letters 17 (2015) 6126–6129; doi:10.1021/acs.orglett.5b03146

data_1540574
_publ_section_title
;
 Synthesis of Functionalized 1H-Isochromene Derivatives via a Au-Catalyzed
 Domino Cycloisomerization/Reduction Approach.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6126
_journal_page_last               6129
_journal_paper_doi               10.1021/acs.orglett.5b03146
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C15 H11 N O3'
_chemical_formula_sum            'C15 H11 N O3'
_chemical_formula_weight         253.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.8450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.1340(3)
_cell_length_b                   7.4180(2)
_cell_length_c                   26.1516(7)
_cell_measurement_reflns_used    9090
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      67.58
_cell_measurement_theta_min      3.38
_cell_volume                     2352.69(11)
_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    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_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     1.54178
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23569
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.194
_diffrn_reflns_theta_min         3.382
_diffrn_source                   'micro focus sealed tube'
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0563
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0826P)^2^+1.0343P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.1566
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3679
_reflns_number_total             4258
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03146_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 1540574.cif.'
_cod_database_code               1540574
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              37884
_shelx_hkl_checksum              23690