The Diastereoselective Synthesis of Pyrroloindolines by Pd-Catalyzed Dearomative Cycloaddition of 1-Tosyl-2-vinylaziridine to 3-Nitroindoles
Rivinoja, Daniel J.; Gee, Yi Sing; Gardiner, Michael G.; Ryan, John H.; Hyland, Christopher J. T.; ACS Catalysis 7 (2017) 1053–; doi:10.1021/acscatal.6b03248

data_4514012
_publ_section_title
;
 The Diastereoselective Synthesis of Pyrroloindolines by Pd-Catalyzed
 Dearomative Cycloaddition of 1-Tosyl-2-vinylaziridine to 3-Nitroindoles
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              1053
_journal_paper_doi               10.1021/acscatal.6b03248
_journal_volume                  7
_journal_year                    2017
_chemical_formula_sum            'C28 H27 N3 O8 S2'
_chemical_formula_weight         597.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 100.543(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.946(3)
_cell_length_b                   13.855(3)
_cell_length_c                   12.2464(14)
_cell_measurement_reflns_used    9752
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.83
_cell_measurement_theta_min      4.15
_cell_volume                     2826.8(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX3 v2016.1-0  (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker AXS PHOTON-100'
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator
'Bruker multilayer X-ray optics (Goebel mirror)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15097
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.778
_diffrn_reflns_theta_min         3.671
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    2.183
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       rod
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1184 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+2.5487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0806
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                3647
_reflns_number_total             3753
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b03248_si_002.cif
_cod_data_source_block           C:\Users\mgg\DOCUME~1\QUESTD~1\16mg002\twin
_cod_original_cell_volume        2826.7(8)
_cod_database_code               4514012
_shelx_estimated_absorpt_t_min   0.669
_shelx_estimated_absorpt_t_max   0.669
_shelxl_version_number           2014-3
_shelx_res_checksum              67577
_shelx_hkl_checksum              93483