One-Pot Relay Gold(I) and Brønsted Acid Catalysis: Cyclopenta[b]annulation of Indoles via Hydroamination/Nazarov-Type Cyclization Cascade of Enynols.
Dhiman, Seema; Ramasastry, S. S. V.; Organic letters 17 (2015) 5116–5119; doi:10.1021/acs.orglett.5b02632

data_1555360
_publ_section_title
;
 One-Pot Relay Gold(I) and Br\/onsted Acid Catalysis:
 Cyclopenta[b]annulation of Indoles via Hydroamination/Nazarov-Type
 Cyclization Cascade of Enynols.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5116
_journal_page_last               5119
_journal_paper_doi               10.1021/acs.orglett.5b02632
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C38 H30 N2 O4 S2'
_chemical_formula_sum            'C38 H30 N2 O4 S2'
_chemical_formula_weight         642.76
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.830(3)
_cell_angle_beta                 105.888(3)
_cell_angle_gamma                110.831(3)
_cell_formula_units_Z            2
_cell_length_a                   9.370(3)
_cell_length_b                   12.582(4)
_cell_length_c                   14.702(4)
_cell_measurement_reflns_used    9576
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.63
_cell_measurement_theta_min      2.41
_cell_volume                     1546.0(8)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0309
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33393
_diffrn_reflns_theta_full        25.18
_diffrn_reflns_theta_max         25.18
_diffrn_reflns_theta_min         1.45
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0547 before and 0.0456 after correction.
The Ratio of minimum to maximum transmission is 0.9404.
The \l/2 correction factor is 0.0015.
;
_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    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.6013P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                4408
_reflns_number_total             5526
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02632_si_002.cif
_cod_data_source_block           sci250_se_12_178_0m
_cod_database_code               1555360
_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 Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C11(H11), C12(H12), C18(H18), C19(H19), C20(H20), C21(H21),
 C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C32(H32), C33(H33),
  C34(H34), C35(H35), C36(H36), C37(H37), C38(H38)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'