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_4022677
_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         'C19 H13 Cl N2 O2 S'
_chemical_formula_sum            'C19 H13 Cl N2 O2 S'
_chemical_formula_weight         368.82
_chemical_name_systematic
4'-(4-Chloro-phenyl)-5-methylsulfanyl-2-phenyl-[4,5']bioxazolyl
_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                90.000(5)
_cell_angle_beta                 106.919(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   10.574(5)
_cell_length_b                   23.386(5)
_cell_length_c                   7.047(5)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.04
_cell_volume                     1667.2(15)
_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 2.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEX '
_diffrn_measurement_method       /w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0648
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10924
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0.05
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_T_max  0.9570
_exptl_absorpt_correction_T_min  0.9432
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.566
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.566
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0602
_refine_ls_shift/su_max          0.213
_refine_ls_shift/su_mean         0.022
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0595P)^2^+0.5614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1982
_reflns_number_gt                3001
_reflns_number_total             4122
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062139jsi20061016_022817.cif
_cod_data_source_block           23
_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/c'
_cod_database_code               4022677