Unexpected Domino Reaction via Pd-Catalyzed Sonogashira Coupling of Benzimidoyl Chlorides with 1,6-Enynes and Cyclization To Synthesize Quinoline Derivatives
Guo-Lin Gao; Yan-Ning Niu; Ze-Yi Yan; Hong-Li Wang; Gang-Wei Wang; Ali Shaukat; Yong-Min Liang; Journal of Organic Chemistry 75 (2010) 1305–1308; doi:10.1021/jo9026116

data_4025245
_publ_section_title
;
 Unexpected Domino Reaction via Pd-Catalyzed Sonogashira Coupling of
 Benzimidoyl Chlorides with 1,6-Enynes and Cyclization To Synthesize
 Quinoline Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1305
_journal_page_last               1308
_journal_paper_doi               10.1021/jo9026116
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C23 H17 N O'
_chemical_formula_weight         323.38
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 126.142(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.7675(10)
_cell_length_b                   8.4494(3)
_cell_length_c                   17.6278(8)
_cell_measurement_reflns_used    1862
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.56
_cell_measurement_theta_min      2.67
_cell_volume                     3460.2(3)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II 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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10004
_diffrn_reflns_theta_full        26.64
_diffrn_reflns_theta_max         26.64
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9769
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0015(3)
_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   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0564P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1286
_reflns_number_gt                2153
_reflns_number_total             3622
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9026116_si_002.cif
_cod_data_source_block           c2c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        3460.2(2)
_cod_database_code               4025245