Formal [3 + 2] Cycloadditions via Indole Activation: A Route to Pyrroloindolines and Furoindolines.
Wang, Ya-Ni; Li, Tian-Ren; Zhang, Mao-Mao; Cheng, Bei-Yi; Lu, Liang-Qiu; Xiao, Wen-Jing; The Journal of organic chemistry 81 (2016) 10491–10498; doi:10.1021/acs.joc.6b00991

data_4036936
_publ_section_title
;
 Formal [3 + 2] Cycloadditions via Indole Activation: A Route to
 Pyrroloindolines and Furoindolines.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10491
_journal_page_last               10498
_journal_paper_doi               10.1021/acs.joc.6b00991
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C20 H22 N2 O2 S'
_chemical_formula_sum            'C20 H22 N2 O2 S'
_chemical_formula_weight         354.45
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.075(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.764(3)
_cell_length_b                   8.3813(18)
_cell_length_c                   15.703(3)
_cell_measurement_reflns_used    4440
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.43
_cell_volume                     1804.4(7)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1029
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8869
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         1.887
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0811
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0773P)^2^+0.7536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1757
_refine_ls_wR_factor_ref         0.1911
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2014
_reflns_number_total             3136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00991_si_001.cif
_cod_data_source_block           t
_cod_database_code               4036936
_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. Restrained distances
 H2-N2
 0.82 with sigma of 0.02
 C10-C19 \\sim C10-C19B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C20B) \\sim Ueq, Uanis(C19B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: C19(0.8) H19(0.8) H10(0.8) H10A(0.2) C20(0.8) H20A(0.8) H20B(0.8)
 C19B(0.2) H19B(0.2) C20B(0.2) H20C(0.2) H20D(0.2)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C10(H10A)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
5.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C5(H5), C3(H3), C2(H2A), C6(H6), C15(H15), C14(H14), C16(H16),
 C17(H17), C19B(H19B)
5.d X=CH2 refined with riding coordinates:
 C20(H20A,H20B), C20B(H20C,H20D)
5.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              68697
_shelx_hkl_checksum              29186
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'