Synthesis of C4-Aminated Indoles via a Catellani and Retro-Diels-Alder Strategy.
Zhang, Bo-Sheng; Li, Yuke; Zhang, Zhe; An, Yang; Wen, Yu-Hua; Gou, Xue-Ya; Quan, Si-Qi; Wang, Xin-Gang; Liang, Yong-Min; Journal of the American Chemical Society 141 (2019) 9731–9738; doi:10.1021/jacs.9b05009

data_4127463
_publ_section_title
;
 Synthesis of C4-Aminated Indoles via a Catellani and Retro-Diels-Alder
 Strategy.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9731
_journal_page_last               9738
_journal_paper_doi               10.1021/jacs.9b05009
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C16 H22 N2 O'
_chemical_formula_sum            'C16 H22 N2 O'
_chemical_formula_weight         258.35
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                85.587(5)
_cell_angle_beta                 88.880(5)
_cell_angle_gamma                73.470(6)
_cell_formula_units_Z            4
_cell_length_a                   9.9395(7)
_cell_length_b                   11.3140(6)
_cell_length_c                   13.5788(8)
_cell_measurement_reflns_used    2220
_cell_measurement_temperature    292.00(10)
_cell_measurement_theta_max      24.1270
_cell_measurement_theta_min      3.6810
_cell_volume                     1459.56(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      292.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -92.00  -66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -77.0000  120.0000 26

  2 omega  -19.00   12.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -77.0000  120.0000 31

  3 omega   35.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000 -120.0000 40

  4 omega  -20.00   68.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000   90.0000 88

  5 omega   65.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000    0.0000 26

  6 omega   41.00   67.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000  -30.0000 26

  7 omega   16.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -30.0000 75

  8 omega  -46.00   46.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -150.0000 92
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0694224000
_diffrn_orient_matrix_UB_12      0.0052423000
_diffrn_orient_matrix_UB_13      0.0165932000
_diffrn_orient_matrix_UB_21      -0.0250368000
_diffrn_orient_matrix_UB_22      0.0161935000
_diffrn_orient_matrix_UB_23      -0.0491755000
_diffrn_orient_matrix_UB_31      0.0097349000
_diffrn_orient_matrix_UB_32      -0.0633296000
_diffrn_orient_matrix_UB_33      -0.0071603000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9817
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.429
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0595
_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^)+(0.0510P)^2^+0.1445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1574
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3507
_reflns_number_total             5730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05009_si_002.cif
_cod_data_source_block           zhangbsh_1121
_cod_depositor_comments
;

2020-04-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C16 H22 N2 O)'
_cod_original_formula_sum        'C32 H44 N4 O2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     516.71
_cod_database_code               4127463
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.988
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C27(H27A,H27B), C37(H37A,H37B), C38(H38A,H38B), C22(H22A,
 H22B), C29(H29A,H29B), C34(H34A,H34B), C35(H35A,H35B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C13(H13), C15(H15), C21(H21), C16(H16), C18(H18), C19(H19),
 C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C30(H30A,H30B,
 H30C), C33(H33A,H33B,H33C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              63673
_shelx_hkl_checksum              90758
_olex2_date_sample_data_collection 2018-11-21
_olex2_submission_special_instructions 'No special instructions were received'