Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer-Cyclization of <i>o</i>-Alkynoylaniline Derivatives.
Saito, Koya; Yoshida, Masahito; Uekusa, Hidehiro; Doi, Takayuki; ACS omega 2 (2017) 4370–4381; doi:10.1021/acsomega.7b00793

data_4516903
_publ_section_title
;
 Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by
 9-AJ-Catalyzed Tandem Acyl Transfer-Cyclization of
 <i>o</i>-Alkynoylaniline Derivatives.
;
_journal_issue                   8
_journal_name_full               'ACS omega'
_journal_page_first              4370
_journal_page_last               4381
_journal_paper_doi               10.1021/acsomega.7b00793
_journal_volume                  2
_journal_year                    2017
_chemical_formula_moiety         'C27 H23.15 N O4.07'
_chemical_formula_sum            'C27 H23.15 N O4.07'
_chemical_formula_weight         426.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 107.6670(12)
_cell_angle_gamma                90
_cell_formula_units_Z            32
_cell_length_a                   39.0066(13)
_cell_length_b                   22.1515(6)
_cell_length_c                   21.6750(6)
_cell_measurement_reflns_used    34931
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.0
_cell_volume                     17845.1(9)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2014/07 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID IP Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            82679
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.438
_diffrn_reflns_theta_min         2.986
_diffrn_source                   'rotating anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       prism
_exptl_crystal_F_000             7192
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1181
_refine_ls_number_reflns         20178
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1405
_refine_ls_R_factor_gt           0.0655
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1200P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.2233
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9714
_reflns_number_total             20178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao7b00793_si_002.cif
_cod_data_source_block           shelx_a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4516903
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.975
_shelx_res_checksum              75711
_shelx_hkl_checksum              4432