Divergent Synthesis of Polycyclic Indolines: Copper-Catalyzed Cascade Reactions of Propargylic Carbamates and Indoles.
Li, Tian-Ren; Lu, Liang-Qiu; Wang, Ya-Ni; Wang, Bao-Cheng; Xiao, Wen-Jing; Organic letters 19 (2017) 4098–4101; doi:10.1021/acs.orglett.7b01903

data_1547123
_publ_section_title
;
 Divergent Synthesis of Polycyclic Indolines: Copper-Catalyzed Cascade
 Reactions of Propargylic Carbamates and Indoles.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              4098
_journal_page_last               4101
_journal_paper_doi               10.1021/acs.orglett.7b01903
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C27 H26 N2 O3 S, C3 H6 O'
_chemical_formula_sum            'C30 H32 N2 O4 S'
_chemical_formula_weight         516.63
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                74.988(3)
_cell_angle_beta                 88.662(3)
_cell_angle_gamma                88.721(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0918(15)
_cell_length_b                   12.255(2)
_cell_length_c                   12.832(2)
_cell_measurement_reflns_used    3224
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      24.45
_cell_measurement_theta_min      2.67
_cell_volume                     1380.4(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9915
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.248
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         1.643
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0888 before and 0.0424 after correction.
The Ratio of minimum to maximum transmission is 0.8767.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4947
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0640
_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^)+(0.1397P)^2^+0.3726P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1948
_refine_ls_wR_factor_ref         0.2261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3476
_reflns_number_total             4947
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01903_si_003.cif
_cod_data_source_block           core1
_cod_database_code               1547123
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C29) \\sim Ueq, Uanis(C30) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
3.a Ternary CH refined with riding coordinates:
 C14(H14), C20(H20)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C23(H23), C24(H24), C25(H25), C26(H26)
3.d X=CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              35133
_shelx_hkl_checksum              59167
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'