Dual-Functionalization of Alkynes via Copper-Catalyzed Carbene/Alkyne Metathesis: A Direct Access to the 4-Carboxyl Quinolines
Yao, Ruwei; Rong, Guangwei; Yan, Bin; Qiu, Lihua; Xu, Xinfang; ACS Catalysis 6 (2016) 1024–; doi:10.1021/acscatal.5b02648

data_4513799
_publ_section_title
;
 Dual-Functionalization of Alkynes via Copper-Catalyzed Carbene/Alkyne
 Metathesis: A Direct Access to the 4-Carboxyl Quinolines
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              1024
_journal_paper_doi               10.1021/acscatal.5b02648
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C22 H13 N O2'
_chemical_formula_sum            'C22 H13 N O2'
_chemical_formula_weight         323.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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                 95.582(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1061(5)
_cell_length_b                   22.232(2)
_cell_length_c                   11.7017(12)
_cell_measurement_reflns_used    871
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      22.1080
_cell_measurement_theta_min      3.9470
_cell_volume                     1581.0(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\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  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0808
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6911
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_correction_T_min  0.9494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0049(4)
_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   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1290
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0111P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0888
_reflns_number_gt                1463
_reflns_number_total             2945
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs5b02648_si_003.cif
_cod_data_source_block           g150921a
_cod_depositor_comments
'Adding full bibliography for 4513798--4513799.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4513799