Synthesis of two distinct pyrrole moiety-containing arenes from nitroanilines using Paal-Knorr followed by an indium-mediated reaction.
Kim, Byeong Hyo; Bae, Seolhee; Go, Ahra; Lee, Hyunseung; Gong, Cheoloh; Lee, Byung Min; Organic & biomolecular chemistry 14 (2015) 265–276; doi:10.1039/c5ob02101d

data_7154800
_publ_section_title
;
 Synthesis of two distinct pyrrole moiety-containing arenes from
 nitroanilines using Paal-Knorr followed by an indium-mediated reaction.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              265
_journal_page_last               276
_journal_paper_doi               10.1039/c5ob02101d
_journal_volume                  14
_journal_year                    2015
_chemical_formula_moiety         C23H22N2
_chemical_formula_sum            'C23 H22 N2'
_chemical_formula_weight         326.43
_chemical_melting_point          161.5(5)
_chemical_name_common
1-(2,5-Dimethyl-1H-pyrrol-1-yl)-4-(2-methyl-5-phenyl-1H-pyrrol-1-yl)benzene
_chemical_name_systematic
; 
 2,5-Dimethyl-1-[4-(2-methyl-5-phenyl-1H-pyrrol-1-yl)phenyl]-1H-pyrrole  
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-07-24 deposited with the CCDC.
2015-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9535(1)
_cell_length_b                   8.5937(1)
_cell_length_c                   30.8423(5)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      26.09
_cell_measurement_theta_min      2.64
_cell_volume                     1843.02(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0088
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4927
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.32
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate/hexane with a trace amount of dichroromethane '
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4581
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0615P)^2^+0.1998P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                3846
_reflns_number_total             4581
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob02101d2.cif
_cod_data_source_block           20150713_pl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '161-162' was changed to '161.5(5)' -
the average value was taken and precision was estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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.

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7154800.cif.
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7154800