An Efficient Highly Regioselective Synthesis of 2,3,4-Trisubstituted Pyrroles by Cycloaddition of Polarized Ketene S,S- and N,S- Acetals with Activated Methylene Isocyanides
N. C. Misra; K. Panda; H. Ila; H. Junjappa; Journal of Organic Chemistry 72 (2007) 1246–1251; doi:10.1021/jo062139j

data_4022676
_publ_contact_author_address
;Dept. of Chemistry
Indian Institute of Technology, Kanpur
India - 208016
;
_publ_contact_author_email       hila@iitk.ac.in
_publ_contact_author_fax         915122597436
_publ_contact_author_name        'H. Ila'
_publ_contact_author_phone       915122597870
_publ_section_title
;
 An Efficient Highly Regioselective Synthesis of 2,3,4-Trisubstituted
 Pyrroles by Cycloaddition of Polarized Ketene S,S- and N,S- Acetals
 with Activated Methylene Isocyanides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1246
_journal_page_last               1251
_journal_paper_doi               10.1021/jo062139j
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         '2(C12 H17 N3 O4), C H Cl3'
_chemical_formula_sum            'C25 H35 Cl3 N6 O8'
_chemical_formula_weight         653.94
_chemical_melting_point          385
_chemical_name_systematic        Ethyl-4-nitro-3-piperidinopyrrole-2-carboxylate
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                102.764(5)
_cell_angle_beta                 100.327(5)
_cell_angle_gamma                100.046(5)
_cell_formula_units_Z            2
_cell_length_a                   9.592(5)
_cell_length_b                   10.049(5)
_cell_length_c                   16.587(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1495.4(12)
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_molecular_graphics    'Diamond 2.1e, Ortep'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.9851
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9838
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.13
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            'Yellowish orange'
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Rectangular block'
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         7072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0166P)^2^+4.2809P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1405
_reflns_number_gt                5533
_reflns_number_total             7072
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062139jsi20061016_022345.cif
_cod_data_source_block           32
_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_database_code               4022676