Nano-copper catalysed highly regioselective synthesis of 2,4-disubstituted pyrroles from terminal alkynes and isocyanides
Dipak Kumar Tiwari; Jaya Pogula; B. Sridhar; Dharmendra Kumar Tiwari; Pravin R. Likhar; Chem.Commun. 51 (2015) 13646–; doi:10.1039/C5cc04166J

data_7117669
_publ_section_title
;
 Nano-copper catalysed highly regioselective synthesis of
 2,4-disubstituted pyrroles from terminal alkynes and isocyanides
;
_journal_name_full               Chem.Commun.
_journal_page_first              13646
_journal_paper_doi               10.1039/C5cc04166J
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C12 H11 N O2'
_chemical_formula_sum            'C12 H11 N O2'
_chemical_formula_weight         201.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-03-13 deposited with the CCDC.
2015-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.969(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7718(8)
_cell_length_b                   5.5207(5)
_cell_length_c                   11.7443(11)
_cell_measurement_reflns_used    4155
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.62
_cell_volume                     503.60(8)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXL-2014
_computing_publication_material  SHELXL-2014
_computing_structure_refinement  SHELXL-2014/7
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5315
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.244
_diffrn_reflns_theta_min         1.735
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SABABS; Bruker,2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 857 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2019
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+0.0387P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0854
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                1968
_reflns_number_total             2019
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc04166j2.cif
_cod_data_source_block           aw73m
_cod_database_code               7117669
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              81603