Copper-Catalyzed Highly Enantioselective Cyclopentannulation of Indoles with Donor-Acceptor Cyclopropanes
Hu Xiong; Hao Xu; Saihu Liao; Zuowei Xie; Yong Tang; Journal of the American Chemical Society 135 (2013) 7851–7854; doi:10.1021/ja4042127

data_4119819
_publ_contact_author_name
;
;
_publ_section_title
;
 Copper-Catalyzed Highly Enantioselective Cyclopentannulation of Indoles
 with Donor-Acceptor Cyclopropanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7851
_journal_page_last               7854
_journal_paper_doi               10.1021/ja4042127
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C35 N3 O6, C4 O2'
_chemical_formula_sum            'C39 H43 N3 O8'
_chemical_formula_weight         681.76
_chemical_name_systematic
;
 ? 
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-09-22
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.148(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.6896(19)
_cell_length_b                   10.0615(10)
_cell_length_c                   19.5653(17)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.356
_cell_measurement_theta_min      2.214
_cell_volume                     3621.6(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v6.02A (Bruker, 2001)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20459
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.11
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.206378
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0816 before and 0.0258 after correction.
The Ratio of minimum to maximum transmission is 0.2064.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.087
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         6733
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0695
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1132P)^2^+1.2182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1910
_refine_ls_wR_factor_ref         0.2242
_reflns_number_gt                3988
_reflns_number_total             6733
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4042127_11.cif
_cod_data_source_block           cd212503
_cod_database_code               4119819