One-Pot Domino Friedel-Crafts Acylation/Annulation between Alkynes and 2-Methoxybenzoyl Chlorides: Synthesis of 2,3-Disubstituted Chromen-4-one Derivatives.
Bam, Radha; Chalifoux, Wesley A.; The Journal of organic chemistry 83 (2018) 9929–9938; doi:10.1021/acs.joc.8b01357

data_4035094
_publ_section_title
;
 One-Pot Domino Friedel-Crafts Acylation/Annulation between Alkynes and
 2-Methoxybenzoyl Chlorides: Synthesis of 2,3-Disubstituted Chromen-4-one
 Derivatives.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9929
_journal_page_last               9938
_journal_paper_doi               10.1021/acs.joc.8b01357
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C23 H22 O3 Si'
_chemical_formula_weight         374.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                106.2708(14)
_cell_angle_beta                 94.4157(15)
_cell_angle_gamma                102.8821(15)
_cell_formula_units_Z            2
_cell_length_a                   8.8996(8)
_cell_length_b                   9.6500(8)
_cell_length_c                   12.1116(10)
_cell_measurement_reflns_used    5370
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.84
_cell_measurement_theta_min      2.27
_cell_volume                     962.50(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22934
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.994
_diffrn_reflns_theta_min         1.771
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5833
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       rod
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         5611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+0.0970P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1313
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4167
_reflns_number_total             5611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01357_si_003.cif
_cod_data_source_block           RB002_0m
_cod_database_code               4035094
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2014/6
_shelx_res_checksum              39789
_shelx_hkl_checksum              23915