The surprising nucleophilic addition of aminochlorocarbenes to diethyl acetylenedicarboxylate and to oxalyl chloride: quinolines and benzo[1,4]diazepines from N-alkylformanilides and oxalyl chloride in the presence of H�nig's base
Cheng, Ying; Yang, Hua; Meth-Cohn, Otto; Organic & Biomolecular Chemistry 1 (2003) 3605–; doi:10.1039/b307278a

data_7151542
_publ_section_title
;
 The surprising nucleophilic addition of aminochlorocarbenes to diethyl
 acetylenedicarboxylate and to oxalyl chloride: quinolines and
 benzo[1,4]diazepines from N-alkylformanilides and oxalyl chloride in
 the presence of H&#xFFFD;nig's base
;
_journal_issue                   20
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              3605
_journal_paper_doi               10.1039/b307278a
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C25 H30 Cl N O9'
_chemical_formula_weight         523.95
_chemical_melting_point          378
_chemical_name_systematic
;
Diethyl 2-(2-chloro-1,2-bis(ethoxy-carbonyl)vinyl)-
6-methoxy1-1-methyl-1,2-dihydroquinoline-3,4-dicarboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.19(3)
_cell_angle_beta                 81.52(3)
_cell_angle_gamma                88.99(3)
_cell_formula_units_Z            2
_cell_length_a                   8.312(12)
_cell_length_b                   8.487(13)
_cell_length_c                   19.91(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1360(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.785
_diffrn_measured_fraction_theta_max 0.785
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1060
_diffrn_reflns_av_sigmaI/netI    0.1181
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4331
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3760
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.411
_refine_ls_R_factor_all          0.1848
_refine_ls_R_factor_gt           0.0803
_refine_ls_shift/su_max          5.027
_refine_ls_shift/su_mean         0.082
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1756
_refine_ls_wR_factor_ref         0.2216
_reflns_number_gt                1667
_reflns_number_total             3760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b307278a.txt
_cod_data_source_block           050702b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' 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-1
_cod_database_code               7151542