Catalytic Divergent Synthesis of 3H or 1H Pyrroles by [3 + 2] Cyclization of Allenoates with Activated Isocyanides.
Liao, Jia-Yu; Shao, Pan-Lin; Zhao, Yu; Journal of the American Chemical Society 137 (2015) 628–631; doi:10.1021/ja511895q

data_4123236
_publ_section_title
;
 Catalytic Divergent Synthesis of 3H or 1H Pyrroles by [3 + 2] Cyclization
 of Allenoates with Activated Isocyanides.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              628
_journal_page_last               631
_journal_paper_doi               10.1021/ja511895q
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C23 H23 N O4'
_chemical_formula_sum            'C23 H23 N O4'
_chemical_formula_weight         377.42
_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   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90.524(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2073(5)
_cell_length_b                   8.4035(4)
_cell_length_c                   12.6305(7)
_cell_measurement_reflns_used    13108
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.628
_cell_measurement_theta_min      3.499
_cell_volume                     977.23(9)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX v2013.2.0'
_computing_data_reduction        'Saint, APEX v2013.2.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX v2013.2.0.'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Sir 2014'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12788
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.628
_diffrn_reflns_theta_min         3.499
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.014
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1685 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.32(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         3778
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0698P)^2^+0.4217P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1352
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                3742
_reflns_number_total             3778
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja511895q_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4123235--4123236.cif.'
_cod_database_code               4123236
_shelx_estimated_absorpt_t_min   0.800
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2014/6
_shelx_res_checksum              11572
_shelx_hkl_checksum              71438