Synthesis of Highly Substituted 2,3-Dihydro-1H-pyrrole Derivatives via a Tandem Regioselective Addition of Nitrones to 1,3-Enynes with Subsequent Rearrangement
Sivaperuman Saravanan; Ismail Abulkalam Azath; Shanmugam Muthusubramanian; Journal of Organic Chemistry 73 (2008) 2323–2329; doi:10.1021/jo702610j

data_4023345
_publ_contact_author_address
;
Department of Organic Chemistry
School of Chemistry
Madurai Kamaraj University
Madurai 625 021
India
;
_publ_contact_author_email       muthumanian2001@yahoo.com
_publ_contact_author_name        'Prof.Shanmugam Muthusubramanian'
_publ_contact_author_phone       '0452 2458246'
_publ_section_title
;
 Synthesis of Highly Substituted 2,3-Dihydro-1H-pyrrole Derivatives
 via a Tandem Regioselective Addition of Nitrones to 1,3-Enynes
 with Subsequent Rearrangement
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2323
_journal_page_last               2329
_journal_paper_doi               10.1021/jo702610j
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C34 H27 Cl2 N2 O4'
_chemical_formula_sum            'C34 H27 Cl2 N2 O4'
_chemical_formula_weight         598.48
_chemical_melting_point          153
_chemical_name_systematic
;
Ethyl 5-(4-chlorobenzoyl)-3-cyano-4-(4-chlorophenyl)-2-(4-methoxyphenyl)-1-
phenyl-2,3-dihydro-1H-pyrrole-3-carboxylate
;
_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_date             '23 August 2007'
_audit_creation_method           SHELXTL/PC
_cell_angle_alpha                90.00
_cell_angle_beta                 106.9530(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.2318(5)
_cell_length_b                   10.6472(4)
_cell_length_c                   19.2838(7)
_cell_measurement_reflns_used    8295
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.92
_cell_measurement_theta_min      2.21
_cell_volume                     2991.47(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20839
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Hexagonal
_exptl_crystal_F_000             1244
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         6973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0788P)^2^+0.6018P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1482
_reflns_number_gt                4966
_reflns_number_total             6973
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702610j-File005.cif
_cod_data_source_block           mku1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023345