Cu-Catalyzed switchable synthesis of functionalized pyridines and pyrroles.
Ling, Zheng; Xie, Fang; Gridnev, Ilya D.; Terada, Masahiro; Zhang, Wanbin; Chemical communications (Cambridge, England) 54 (2018) 9446–9449; doi:10.1039/c8cc05307c

data_7122069
_publ_section_title
;
 Cu-Catalyzed switchable synthesis of functionalized pyridines and
 pyrroles.
;
_journal_issue                   68
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9446
_journal_page_last               9449
_journal_paper_doi               10.1039/c8cc05307c
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         '3(C19 H15 N O2), C19 H14 N O2'
_chemical_formula_sum            'C76 H59 N4 O8'
_chemical_formula_weight         1156.27
_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   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-08-21 deposited with the CCDC.
2018-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.124(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8509(3)
_cell_length_b                   13.4787(4)
_cell_length_c                   22.2482(7)
_cell_measurement_reflns_used    9808
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      3.84
_cell_volume                     2937.20(16)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24116
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.402
_diffrn_reflns_theta_min         3.279
_exptl_absorpt_coefficient_mu    0.681
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             1214
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 2999 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.36(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     798
_refine_ls_number_reflns         10150
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0960
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1928P)^2^+1.1939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2505
_refine_ls_wR_factor_ref         0.2761
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                8409
_reflns_number_total             10150
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc05307c2.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 7122069--7122070.cif.'
_cod_database_code               7122069
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              48294