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_4036610
_publ_section_title
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 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.
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_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            'C20 H18 O3'
_chemical_formula_weight         306.34
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.9800(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6299(7)
_cell_length_b                   18.125(2)
_cell_length_c                   15.3048(18)
_cell_measurement_reflns_used    7582
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.25
_cell_volume                     1555.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13122
_diffrn_reflns_theta_full        27.64
_diffrn_reflns_theta_max         27.64
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_correction_T_min  0.9802
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0137(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+0.2334P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                2988
_reflns_number_total             3558
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00001_si_003.cif
_cod_data_source_block           150721a_0m
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
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_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4036610