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_4032166
_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         'C38 H32 N2 O2'
_chemical_formula_sum            'C38 H32 N2 O2'
_chemical_formula_weight         548.65
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2016-11-26
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5263)
;
_cell_angle_alpha                101.114(4)
_cell_angle_beta                 104.653(4)
_cell_angle_gamma                97.215(4)
_cell_formula_units_Z            2
_cell_length_a                   9.8605(16)
_cell_length_b                   10.2577(16)
_cell_length_c                   15.126(2)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.24
_cell_volume                     1427.7(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.1669
_diffrn_reflns_av_unetI/netI     0.1294
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_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       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            63640
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.607
_diffrn_reflns_theta_min         2.215
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_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    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Flack x determined using 2683 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(8)
_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     759
_refine_ls_number_reflns         12512
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1467
_refine_ls_R_factor_gt           0.0602
_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^)+(0.0526P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1296
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                7388
_reflns_number_total             12512
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02947_si_003.cif
_cod_data_source_block           b161125b_0m_a
_cod_depositor_comments
;
         Adding full bibliography for 4032166.cif.

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C38 H32 N2 O2)'
_cod_original_formula_sum        'C76 H64 N4 O4'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     1097.31
_cod_database_code               4032166
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.984
_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:
 C32(H32), C76(H76)
2.b Secondary CH2 refined with riding coordinates:
 C3BA(H3BA,H3BB), C7(H7A,H7B), C74(H74A,H74B), C75(H75A,H75B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C25(H25), C26(H26), C27(H27),
  C28(H28), C29(H29), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38),
 C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C50(H50), C51(H51), C52(H52),
  C53(H53), C54(H54), C55(H55), C56(H56), C58(H58), C59(H59), C60(H60),
 C62(H62), C63(H63), C65(H65), C66(H66), C68(H68), C69(H69), C70(H70), C71(H71),
  C72(H72)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C61(H61A,H61B,H61C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'