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_1553830
_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         'C27 H33 N O7 S'
_chemical_formula_sum            'C27 H33 N O7 S'
_chemical_formula_weight         515.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-03-22 deposited with the CCDC.
2017-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.806(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.7047(6)
_cell_length_b                   15.4463(7)
_cell_length_c                   24.0895(10)
_cell_measurement_reflns_used    1662
_cell_measurement_temperature    290.74(10)
_cell_measurement_theta_max      23.4310
_cell_measurement_theta_min      3.6690
_cell_volume                     5052.2(4)
_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      290.74(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.8982
_diffrn_measurement_details
;
  1 omega  -14.00   12.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -99.0000  150.0000 26

  2 omega  -50.00   56.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -77.0000  -30.0000 106

  3 omega   53.00   89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  178.0000 -180.0000 36

  4 omega  -11.00   89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -19.0000 -180.0000 100
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0030337000
_diffrn_orient_matrix_UB_12      0.0131535000
_diffrn_orient_matrix_UB_13      -0.0283988000
_diffrn_orient_matrix_UB_21      0.0401352000
_diffrn_orient_matrix_UB_22      0.0286711000
_diffrn_orient_matrix_UB_23      0.0072458000
_diffrn_orient_matrix_UB_31      0.0333096000
_diffrn_orient_matrix_UB_32      -0.0333464000
_diffrn_orient_matrix_UB_33      -0.0049806000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11127
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.40
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79692
_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    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0598
_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^)+(0.0293P)^2^+1.0822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1244
_reflns_number_gt                2958
_reflns_number_total             4967
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00511c2.cif
_cod_data_source_block           sunhy_1216
_cod_database_code               1553830
_reflns_odcompleteness_completeness 99.70
_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 Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C20(H20), C21(H21), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C25(H25A,H25B,H25C)
;
_olex2_date_sample_data_collection 2016-12-16
_olex2_submission_special_instructions 'No special instructions were received'