Rapid construction of complex tetracyclic frameworks via a gold(i)-catalyzed tandem 1,2-acyloxy migration/[3 + 2] cycloaddition/Friedel–Crafts type cyclization reaction of linear enynyl esters
Sun, Haiyu; Xu, Shiyan; Xing, Zhimin; Liu, Lin; Feng, Shangbiao; Fang, Bowen; Xie, Xingang; She, Xuegong; Organic Chemistry Frontiers 4 (2017) 2109–; doi:10.1039/C7QO00511C

data_1553828
_publ_section_title
;
 Rapid construction of complex tetracyclic frameworks via a
 gold(i)-catalyzed tandem 1,2-acyloxy migration/[3 + 2]
 cycloaddition/Friedel--Crafts type cyclization reaction of linear enynyl
 esters
;
_journal_issue                   11
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2109
_journal_paper_doi               10.1039/C7QO00511C
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C18 H22 O6'
_chemical_formula_sum            'C18 H22 O6'
_chemical_formula_weight         334.36
_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             2016-05-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-03-22 deposited with the CCDC.
2017-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                115.731(8)
_cell_angle_beta                 104.925(7)
_cell_angle_gamma                90.322(6)
_cell_formula_units_Z            2
_cell_length_a                   8.9279(6)
_cell_length_b                   10.0249(7)
_cell_length_c                   10.8557(10)
_cell_measurement_reflns_used    1999
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.6820
_cell_measurement_theta_min      3.9320
_cell_volume                     838.00(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -51.00   32.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -19.0000 -150.0000 83

  2 omega  -13.00   24.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000 -120.0000 37

  3 omega  -19.00   54.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -99.0000 -150.0000 73

  4 omega   -4.00   22.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000    0.0000 26

  5 omega  -47.00   42.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000  -30.0000 89

  6 omega  -26.00   33.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000   90.0000 59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0346811000
_diffrn_orient_matrix_UB_12      -0.0046339000
_diffrn_orient_matrix_UB_13      -0.0685623000
_diffrn_orient_matrix_UB_21      -0.0255750000
_diffrn_orient_matrix_UB_22      -0.0771535000
_diffrn_orient_matrix_UB_23      -0.0269431000
_diffrn_orient_matrix_UB_31      -0.0709141000
_diffrn_orient_matrix_UB_32      0.0175785000
_diffrn_orient_matrix_UB_33      0.0176645000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5535
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.51
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0352P)^2^+0.3160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                2389
_reflns_number_total             3290
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00511c2.cif
_cod_data_source_block           sunhy_0509
_cod_original_cell_volume        838.00(11)
_cod_database_code               1553828
_reflns_odcompleteness_completeness 99.62
_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 Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_olex2_date_sample_data_collection 2016-05-09
_olex2_submission_special_instructions 'No special instructions were received'