FeCl3-Mediated One-Pot Domino Reactions for the Synthesis of 9-Aryl/9-Arylethynyl-2,3,4,9-tetrahydro-1H-xanthen-1-ones from Propargylic Amines/Diaryl Amines and 1,3-Cyclohexanediones.
He, Xinwei; Tao, Jiajia; Hu, Xiaoqian; Wang, Hui; Shang, Yongjia; The Journal of organic chemistry 81 (2016) 2062–2069; doi:10.1021/acs.joc.6b00001

data_4036609
_publ_section_title
;
 FeCl3-Mediated One-Pot Domino Reactions for the Synthesis of
 9-Aryl/9-Arylethynyl-2,3,4,9-tetrahydro-1H-xanthen-1-ones from
 Propargylic Amines/Diaryl Amines and 1,3-Cyclohexanediones.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2062
_journal_page_last               2069
_journal_paper_doi               10.1021/acs.joc.6b00001
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C21 H15 Br O2'
_chemical_formula_weight         379.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 104.9610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.7257(17)
_cell_length_b                   8.6177(9)
_cell_length_c                   12.0468(12)
_cell_measurement_reflns_used    5509
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.52
_cell_volume                     1677.5(3)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14122
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.644
_diffrn_reflns_theta_min         2.521
_diffrn_source                   graphite
_exptl_absorpt_coefficient_mu    2.460
_exptl_absorpt_correction_T_max  0.7568
_exptl_absorpt_correction_T_min  0.7246
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3878
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0628P)^2^+0.5865P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2891
_reflns_number_total             3878
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00001_si_002.cif
_cod_data_source_block           131227a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036609
_shelx_estimated_absorpt_t_min   0.725
_shelx_estimated_absorpt_t_max   0.757
_shelxl_version_number           2013-4
_shelx_res_checksum              80373
_shelx_hkl_checksum              10983