A Metal-Free Domino Process for Regioselective Synthesis of 1,2,4-Trisubstituted Pyrroles: Application toward the Formal Synthesis of Ningalin B.
Kumar, Virendra; Awasthi, Annapurna; Metya, Abhisek; Khan, Tabrez; The Journal of organic chemistry 84 (2019) 11581–11595; doi:10.1021/acs.joc.9b01520

data_4034502
_publ_section_title
;
 A Metal-Free Domino Process for Regioselective Synthesis of
 1,2,4-Trisubstituted Pyrroles: Application toward the Formal Synthesis of
 Ningalin B.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11581
_journal_page_last               11595
_journal_paper_doi               10.1021/acs.joc.9b01520
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C17 H21 N O3'
_chemical_formula_weight         287.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                85.979(18)
_cell_angle_beta                 88.879(19)
_cell_angle_gamma                88.814(17)
_cell_formula_units_Z            4
_cell_length_a                   9.736(4)
_cell_length_b                   11.089(4)
_cell_length_c                   15.026(6)
_cell_measurement_reflns_used    58095
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.455
_cell_measurement_theta_min      2.211
_cell_volume                     1617.6(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            58095
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.455
_diffrn_reflns_theta_min         2.211
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.081
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       Block
_exptl_crystal_F_000             616
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         8012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0719P)^2^+0.6919P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1631
_refine_ls_wR_factor_ref         0.1932
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4990
_reflns_number_total             8012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01520_si_002.cif
_cod_data_source_block           mo_AM_06_0m
_cod_depositor_comments
;

2020-04-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1617.7(11)
_cod_original_formula_sum        'C34 H42 N2 O6'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     574.69
_cod_database_code               4034502
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              88023
_shelx_hkl_checksum              46613