Silver-Catalyzed Domino Reaction of ortho-Carbonylated Alkynyl-Substituted Arylaldehydes with Conjugated Dienes: Stereoselective Access to Indanone-Fused Cyclohexenes.
Cao, Ziping; Zhu, Hongbo; Meng, Xin; Tian, Laijin; Chen, Guang; Sun, Xuejun; You, Jinmao; The Journal of organic chemistry 81 (2016) 12401–12407; doi:10.1021/acs.joc.6b02529

data_4037464
_publ_section_title
;
 Silver-Catalyzed Domino Reaction of ortho-Carbonylated
 Alkynyl-Substituted Arylaldehydes with Conjugated Dienes: Stereoselective
 Access to Indanone-Fused Cyclohexenes.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12401
_journal_page_last               12407
_journal_paper_doi               10.1021/acs.joc.6b02529
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C17 H17 F O2'
_chemical_formula_sum            'C17 H17 F O2'
_chemical_formula_weight         272.31
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.025(2)
_cell_angle_beta                 81.176(2)
_cell_angle_gamma                67.159(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3831(8)
_cell_length_b                   8.4932(9)
_cell_length_c                   11.0905(11)
_cell_measurement_reflns_used    236
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.36
_cell_volume                     691.69(12)
_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      295(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Apex CCD'
_diffrn_measurement_method       '\f and \w 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  0.0123
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4488
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_correction_T_min  0.9672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0721P)^2^+0.1276P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                2300
_reflns_number_total             2714
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02529_si_002.cif
_cod_data_source_block           sad
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4037464