Palladium(0)-Catalyzed Dearomative [3 + 2] Cycloaddition of 3-Nitroindoles with Vinylcyclopropanes: An Entry to Stereodefined 2,3-Fused Cyclopentannulated Indoline Derivatives
Laugeois, Maxime; Ling, Johanne; Férard, Charlène; Michelet, Véronique; Ratovelomanana-Vidal, Virginie; Vitale, Maxime R.; Organic Letters  (2017) –; doi:10.1021/acs.orglett.7b00784

data_1545755
_publ_section_title
;
 Palladium(0)-Catalyzed Dearomative [3 + 2] Cycloaddition of
 3-Nitroindoles with Vinylcyclopropanes: An Entry to Stereodefined
 2,3-Fused Cyclopentannulated Indoline Derivatives
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.7b00784
_journal_year                    2017
_chemical_formula_moiety         'C22  H16  N4  O3'
_chemical_formula_sum            'C22 H16 N4 O3'
_chemical_formula_weight         384.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.310(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.507(3)
_cell_length_b                   6.5815(6)
_cell_length_c                   25.139(3)
_cell_measurement_reflns_used    400
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      61.61
_cell_measurement_theta_min      4.61
_cell_volume                     3768.6(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker Apex2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            41536
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.362
_diffrn_reflns_theta_min         2.965
_diffrn_source                   'micro focus sealed tube'
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00051(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         6853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0299P)^2^+1.2496P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1356
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4903
_reflns_number_total             6853
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00784_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               1545755
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              95997
_shelx_hkl_checksum              92216