Gold-Catalyzed Tandem Dual Heterocyclization of Enynones with 1,3,5-Triazines: Bicyclic Furan Synthesis and Mechanistic Insights.
Zheng, Yang; Chi, Yongjian; Bao, Ming; Qiu, Lihua; Xu, Xinfang; The Journal of organic chemistry 82 (2017) 2129–2135; doi:10.1021/acs.joc.6b02947

data_4032281
_publ_section_title
;
 Gold-Catalyzed Tandem Dual Heterocyclization of Enynones with
 1,3,5-Triazines: Bicyclic Furan Synthesis and Mechanistic Insights.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2129
_journal_page_last               2135
_journal_paper_doi               10.1021/acs.joc.6b02947
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C37 H30 N2 O'
_chemical_formula_sum            'C37 H30 N2 O'
_chemical_formula_weight         518.63
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-13
_audit_creation_method
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Olex2 1.2-alpha
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
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_cell_angle_alpha                101.808(7)
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_cell_formula_units_Z            2
_cell_length_a                   7.8935(7)
_cell_length_b                   10.8422(10)
_cell_length_c                   17.1058(14)
_cell_measurement_reflns_used    3771
_cell_measurement_temperature    213.50(10)
_cell_measurement_theta_max      26.6660
_cell_measurement_theta_min      3.1870
_cell_volume                     1391.0(2)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      213.50(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -65.00   47.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514  -77.0000 -120.0000 112

  2 omega   26.00   55.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514  -99.0000  150.0000 29

  3 omega  -58.00   31.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514  -57.0000  120.0000 89

  4 omega   35.00   80.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514  178.0000   90.0000 45

  5 omega  -94.00  -60.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327 -178.0000 -150.0000 34

  6 omega  -24.00   28.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327  -99.0000    0.0000 52
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0742665000
_diffrn_orient_matrix_UB_12      -0.0206858000
_diffrn_orient_matrix_UB_13      0.0145695000
_diffrn_orient_matrix_UB_21      -0.0073972000
_diffrn_orient_matrix_UB_22      -0.0446364000
_diffrn_orient_matrix_UB_23      -0.0374592000
_diffrn_orient_matrix_UB_31      0.0547598000
_diffrn_orient_matrix_UB_32      0.0477254000
_diffrn_orient_matrix_UB_33      -0.0146676000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11929
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.936
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.238
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0436P)^2^+0.0839P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3779
_reflns_number_total             5677
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02947_si_002.cif
_cod_data_source_block           g160912b
_cod_database_code               4032281
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26),
  C27(H27), C28(H28), C29(H29), C30(H30), C33(H33), C34(H34), C35(H35),
 C36(H36), C37(H37)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'