Iron-catalyzed synthesis of polysubstituted pyrroles via [4C+1N] cyclization of 4-acetylenic ketones with primary amines
Yeming Wang; Xihe Bi; Dehua Li; Peiqiu Liao; Yidong Wang; Jin Yang; Qian Zhang; Qun Liu; Chem.Commun. 47 (2011) 809–; doi:10.1039/c0cc03802d

data_7105822
_publ_section_title
;
 Iron-catalyzed synthesis of polysubstituted pyrroles via [4C+1N]
 cyclization of 4-acetylenic ketones with primary amines
;
_journal_name_full               Chem.Commun.
_journal_page_first              809
_journal_paper_doi               10.1039/c0cc03802d
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C19 H17 Cl N2 O'
_chemical_formula_sum            'C19 H17 Cl N2 O'
_chemical_formula_weight         324.80
_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                 97.444(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            8
_cell_length_a                   16.137(5)
_cell_length_b                   10.330(5)
_cell_length_c                   20.677(5)
_cell_measurement_reflns_used    6026
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.84
_cell_measurement_theta_min      3.01
_cell_volume                     3418(2)
_computing_cell_refinement       CrysAlis
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2006)'
_computing_data_reduction        CrysAlis
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0943
_diffrn_reflns_av_sigmaI/netI    0.0763
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22036
_diffrn_reflns_theta_full        67.84
_diffrn_reflns_theta_max         67.84
_diffrn_reflns_theta_min         4.31
_exptl_absorpt_coefficient_mu    2.015
_exptl_absorpt_correction_T_max  0.851
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis (Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.852
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         6026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.852
_refine_ls_R_factor_all          0.1401
_refine_ls_R_factor_gt           0.0696
_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^)+(0.1075P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1624
_refine_ls_wR_factor_ref         0.1976
_reflns_number_gt                2655
_reflns_number_total             6026
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            C0CC03802D.TXT
_cod_data_source_block           091125-lq01-gj
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7105822