Expedient synthesis of tetrasubstituted pyrroles via a copper-catalyzed cascade inter-/intramolecular cyclization of 1,3-enynes carry a nitro group with amines.
Bharathiraja, Ganesan; Sengoden, Mani; Kannan, Masanam; Punniyamurthy, Tharmalingam; Organic & biomolecular chemistry 13 (2015) 2786–2792; doi:10.1039/c4ob02508c

data_7154287
_publ_section_title
;
 Expedient synthesis of tetrasubstituted pyrroles via a copper-catalyzed
 cascade inter-/intramolecular cyclization of 1,3-enynes carry a nitro
 group with amines.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2786
_journal_page_last               2792
_journal_paper_doi               10.1039/c4ob02508c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C22 H15 I N2 O2'
_chemical_formula_sum            'C22 H15 I N2 O2'
_chemical_formula_weight         466.26
_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
_audit_update_record
;
2014-09-24 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.431(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5097(4)
_cell_length_b                   10.4987(4)
_cell_length_c                   19.3484(7)
_cell_measurement_reflns_used    5570
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.41
_cell_measurement_theta_min      2.87
_cell_volume                     1919.58(13)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21987
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    1.687
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_correction_T_min  0.609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             920
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3384
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0378
_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^)+(0.1000P)^2^+0.4123P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                2577
_reflns_number_total             3384
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob02508c2.cif
_cod_data_source_block           gbr-595-a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 7154287.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7154287