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_1553826
_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         'C20 H26 O6'
_chemical_formula_sum            'C20 H26 O6'
_chemical_formula_weight         362.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-05-03 deposited with the CCDC.
2017-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.741(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.2811(5)
_cell_length_b                   28.3515(9)
_cell_length_c                   12.9191(5)
_cell_measurement_reflns_used    1573
_cell_measurement_temperature    291.08(10)
_cell_measurement_theta_max      23.0960
_cell_measurement_theta_min      3.6870
_cell_volume                     3657.9(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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      291.08(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.8780
_diffrn_measurement_details
;
  1 omega   -3.00   92.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  150.0000 95

  2 omega   56.00   82.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  -60.0000 26

  3 omega   63.00   95.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000 -120.0000 32

  4 omega   -8.00   64.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000   60.0000 72
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0068386000
_diffrn_orient_matrix_UB_12      -0.0114091000
_diffrn_orient_matrix_UB_13      0.0473082000
_diffrn_orient_matrix_UB_21      0.0704880000
_diffrn_orient_matrix_UB_22      0.0005192000
_diffrn_orient_matrix_UB_23      0.0198387000
_diffrn_orient_matrix_UB_31      -0.0051583000
_diffrn_orient_matrix_UB_32      0.0222606000
_diffrn_orient_matrix_UB_33      0.0237425000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.1089
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13777
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     484
_refine_ls_number_reflns         7182
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1557
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1747
_reflns_number_gt                3263
_reflns_number_total             7182
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00511c2.cif
_cod_data_source_block           sunhy_0111_1
_cod_original_cell_volume        3658.0(2)
_cod_database_code               1553826
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 99.73
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O9) \\sim Ueq, Uanis(O9') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: H27A(0.85) H27B(0.85) H27C(0.15) H27D(0.15) H28A(0.85) H28B(0.85)
 H28C(0.15) H28D(0.15) O9(0.77) O9'(0.23)
4.a Ternary CH refined with riding coordinates:
 C31(H31), C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C27(H27C,H27D), C28(H28A,H28B), C28(H28C,H28D), C30(H30A,
 H30B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C7(H7A,
 H7B), C8(H8A,H8B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,
 H14B), C15(H15A,H15B)
4.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C25(H25), C3(H3), C5(H5)
4.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_olex2_date_sample_data_collection 2017-01-11
_olex2_submission_special_instructions 'No special instructions were received'