Gold-Catalyzed Selective 6-exo-dig and 7-endo-dig Cyclizations of Alkyn-Tethered Indoles To Prepare Rutaecarpine Derivatives.
Kong, Xiang-Fei; Zhan, Feng; He, Guo-Xue; Pan, Cheng-Xue; Gu, Chen-Xi; Lu, Ke; Mo, Dong-Liang; Su, Gui-Fa; The Journal of organic chemistry 83 (2018) 2006–2017; doi:10.1021/acs.joc.7b02956

data_4034981
_publ_section_title
;
 Gold-Catalyzed Selective 6-exo-dig and 7-endo-dig Cyclizations of
 Alkyn-Tethered Indoles To Prepare Rutaecarpine Derivatives.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2006
_journal_page_last               2017
_journal_paper_doi               10.1021/acs.joc.7b02956
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C20 H14 Cl N3 O'
_chemical_formula_sum            'C20 H14 Cl N3 O'
_chemical_formula_weight         347.79
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-08-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                80.568(7)
_cell_angle_beta                 88.970(7)
_cell_angle_gamma                79.020(7)
_cell_formula_units_Z            4
_cell_length_a                   7.489(4)
_cell_length_b                   11.278(5)
_cell_length_c                   19.529(9)
_cell_measurement_reflns_used    7695
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.698
_cell_measurement_theta_min      2.580
_cell_volume                     1597.2(13)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17960
_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         25.348
_diffrn_reflns_theta_min         1.057
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_correction_T_min  0.9512
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         5832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0588P)^2^+0.4983P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1126
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4728
_reflns_number_total             5832
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02956_si_003.cif
_cod_data_source_block           aaaa
_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(C20 H14 Cl N3 O)'
_cod_original_formula_sum        'C40 H28 Cl2 N6 O2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     695.58
_cod_database_code               4034981
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.951
_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:
 C5(H5A,H5B), C37(H37A,H37B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C19(H19),
 C20(H20), C22(H22), C23(H23), C29(H29), C30(H30), C31(H31), C32(H32), C35(H35),
  C36(H36), C40(H40)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              30578
_shelx_hkl_checksum              32816
_olex2_submission_special_instructions 'No special instructions were received'