IBX-Promoted Oxidative Cyclization of N-Hydroxyalkyl Enamines: A Metal-free Approach towards 2,3-Disubstituted Pyrroles and Pyridines.
Gao, Peng; Chen, Huai-Juan; Bai, Zi-Jing; Zhao, Mi-Na; Yang, Desuo; Wang, Juan; Wang, Ning; Du, Lele; Guan, Zheng-Hui; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00625

data_4038467
_publ_section_title
;
 IBX-Promoted Oxidative Cyclization of N-Hydroxyalkyl Enamines: A
 Metal-free Approach towards 2,3-Disubstituted Pyrroles and Pyridines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00625
_journal_year                    2020
_chemical_formula_sum            'C12 H11 N O2'
_chemical_formula_weight         201.22
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.697(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.858(3)
_cell_length_b                   9.1867(18)
_cell_length_c                   18.757(4)
_cell_measurement_reflns_used    3866
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.95
_cell_measurement_theta_min      2.49
_cell_volume                     2143.1(8)
_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(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10344
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9723
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0191(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0540P)^2^+0.5537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                2954
_reflns_number_total             3804
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00625_si_002.cif
_cod_data_source_block           xb1158_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        2143.2(7)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4038467