Skraup-Doebner-Von Miller Quinoline Synthesis Revisited: Reversal of the Regiochemistry for γ-Aryl-β,γ-unsaturated α-Ketoesters
Yan-Chao Wu; Li Liu; Hui-Jing Li; Dong Wang; Yong-Jun Chen; Journal of Organic Chemistry 71 (2006) 6592–6595; doi:10.1021/jo060290n

data_4021870
_publ_section_title
;
 Skraup-Doebner-Von Miller Quinoline Synthesis Revisited:
 Reversal of the Regiochemistry for \g-Aryl-\b,\g-unsaturated
 \a-Ketoesters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6592
_journal_page_last               6595
_journal_paper_doi               10.1021/jo060290n
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C18 H13 Cl2 N O2'
_chemical_formula_weight         346.19
_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                 98.8060(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3615(4)
_cell_length_b                   8.4311(4)
_cell_length_c                   18.5887(6)
_cell_measurement_reflns_used    15356
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.22
_cell_volume                     1604.75(11)
_computing_cell_refinement       'RAPID AUTO (Rigaku, 2001)'
_computing_data_collection       'RAPID AUTO (Rigaku, 2001)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2001)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1994)'
_computing_publication_material  'SHELXTL (Siemens, 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-axis RAPID IP Area detector'
_diffrn_measurement_method       Oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            3660
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.413
_exptl_absorpt_correction_T_max  0.8820
_exptl_absorpt_correction_T_min  0.8297
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Abscor
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.824
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.824
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0751P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                2561
_reflns_number_total             3660
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060290nsi20060212_024930.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Empirical' changed to 'empirical'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4021870