Selective Synthesis of 4-Alkylidene-β-lactams and N,N'-Diarylamidines from Azides and Aryloxyacetyl Chlorides via a Ketenimine-Participating One-Pot Cascade Process
Yun-Yun Yang; Wang-Ge Shou; Deng Hong; Yan-Guang Wang; Journal of Organic Chemistry 73 (2008) 3574–3577; doi:10.1021/jo702733h

data_4023379
_publ_section_title
;
 Selective Synthesis of 4-Alkylidene-\b-lactams and
 N,N'-Diarylamidines from Azides and Aryloxyacetyl Chlorides via a
 Ketenimine-Participating One-Pot Cascade Process
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3574
_journal_page_last               3577
_journal_paper_doi               10.1021/jo702733h
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H19 Cl2 N O3'
_chemical_formula_weight         440.30
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 99.761(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.820(2)
_cell_length_b                   13.703(4)
_cell_length_c                   10.394(3)
_cell_measurement_reflns_used    2415
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.398
_cell_measurement_theta_min      4.965
_cell_volume                     1097.7(5)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0692
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            5943
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75187
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.486
_exptl_crystal_size_mid          0.422
_exptl_crystal_size_min          0.347
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(8)
_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   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4287
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0884P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1434
_reflns_number_gt                3290
_reflns_number_total             4287
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702733h-File004.cif
_cod_data_source_block           cd27165
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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'
_cod_database_code               4023379