Highly Enantioselective Copper- and Iron-Catalyzed Intramolecular Cyclopropanation of Indoles.
Xu, Huan; Li, Yi-Pan; Cai, Yan; Wang, Guo-Peng; Zhu, Shou-Fei; Zhou, Qi-Lin; Journal of the American Chemical Society 139 (2017) 7697–7700; doi:10.1021/jacs.7b03086

data_4131291
_publ_section_title
;
 Highly Enantioselective Copper- and Iron-Catalyzed Intramolecular
 Cyclopropanation of Indoles.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7697
_journal_page_last               7700
_journal_paper_doi               10.1021/jacs.7b03086
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H21 N O4'
_chemical_formula_sum            'C22 H21 N O4'
_chemical_formula_weight         363.40
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                70.180(12)
_cell_angle_beta                 62.360(10)
_cell_angle_gamma                86.860(15)
_cell_formula_units_Z            2
_cell_length_a                   10.2122(8)
_cell_length_b                   10.3040(10)
_cell_length_c                   10.7741(12)
_cell_measurement_reflns_used    1243
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      71.90
_cell_measurement_theta_min      27.70
_cell_volume                     937.7(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r5'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r5'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 11.11
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Rigaku Saturn70 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19828
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         72.48
_diffrn_reflns_theta_min         4.60
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  0.8934
_exptl_absorpt_correction_T_min  0.8575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(19)
_refine_ls_extinction_coef       0.149(5)
_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   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         5797
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0583
_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^)+(0.0678P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                5206
_reflns_number_total             5797
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            5a-cif.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        937.67(20)
_cod_database_code               4131291