Lewis acid-catalyzed one-pot, three-component route to chiral 3,3'-bipyrroles
Dey, Sumit; Pal, Churala; Nandi, Debkumar; Giri, Venkatachalam Sesha; Zaidlewicz, Marek; Krzeminski, Marek; Smentek, Lidia; Hess, Jr, B Andes; Gawronski, Jacek; Kwit, Marcin; Babu, N. Jagadeesh; Nangia, Ashwini; Jaisankar, Parasuraman; Organic letters 10 (2008) 1373–1376; doi:10.1021/ol800115p

data_1504580
_publ_section_title
;
 Lewis acid-catalyzed one-pot, three-component route to chiral
 3,3'-bipyrroles
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1373
_journal_page_last               1376
_journal_paper_doi               10.1021/ol800115p
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C28 H28 N2 O4'
_chemical_formula_sum            'C28 H28 N2 O4'
_chemical_formula_weight         456.52
_chemical_melting_point          568.0(10)
_chemical_name_common            '3,3'-Bipyrrole ester'
_chemical_name_systematic
;
5,5'-Dimethyl-2,2'-diphenyl-1H,1'H-[3,3']-bipyrrolyl-4,4'-dicarboxylic 
acid diethyl ester
;
_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                116.306(13)
_cell_angle_beta                 91.069(15)
_cell_angle_gamma                104.607(14)
_cell_formula_units_Z            2
_cell_length_a                   9.465(8)
_cell_length_b                   12.243(10)
_cell_length_c                   12.556(10)
_cell_measurement_reflns_used    2442
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.56
_cell_measurement_theta_min      2.51
_cell_volume                     1247.8(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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0854
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11705
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_correction_T_min  0.9681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4248
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1567
_refine_ls_R_factor_gt           0.0976
_refine_ls_shift/su_max          2.845
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0979P)^2^+1.0972P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2176
_refine_ls_wR_factor_ref         0.2480
_reflns_number_gt                2551
_reflns_number_total             4248
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800115p-file003.cif
_cod_data_source_block           an698
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '567-569' was changed to '568.0(10)'
- the average value was taken and precision was
estimated.

'_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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               1504580