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_1553831
_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         'C19 H24 O5'
_chemical_formula_sum            'C19 H24 O5'
_chemical_formula_weight         332.38
_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
_audit_creation_date             2016-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-05-03 deposited with the CCDC.
2017-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                66.11(3)
_cell_angle_beta                 71.31(3)
_cell_angle_gamma                87.32(2)
_cell_formula_units_Z            2
_cell_length_a                   8.981(2)
_cell_length_b                   10.331(3)
_cell_length_c                   10.885(3)
_cell_measurement_reflns_used    873
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.5220
_cell_measurement_theta_min      3.7120
_cell_volume                     870.7(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
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      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -92.00  -10.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -38.0000 -120.0000 41

  2 omega   -4.00   22.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  -90.0000 13

  3 omega   -1.00   93.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  150.0000 47

  4 omega  -19.00   57.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000 -120.0000 38

  5 omega  -46.00   46.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000    0.0000 46
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0127014000
_diffrn_orient_matrix_UB_12      0.0452431000
_diffrn_orient_matrix_UB_13      -0.0725323000
_diffrn_orient_matrix_UB_21      -0.0560473000
_diffrn_orient_matrix_UB_22      0.0441779000
_diffrn_orient_matrix_UB_23      0.0209827000
_diffrn_orient_matrix_UB_31      0.0609309000
_diffrn_orient_matrix_UB_32      0.0411482000
_diffrn_orient_matrix_UB_33      0.0001539000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5319
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.389
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.067(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3422
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0673
_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^)+(0.0443P)^2^+0.4217P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1744
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1837
_reflns_number_total             3422
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00511c2.cif
_cod_data_source_block           sunhy_1108
_cod_original_cell_volume        870.6(5)
_cod_database_code               1553831
_reflns_odcompleteness_completeness 99.75
_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(C9') \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: H8AA(0.75) H8AB(0.75) H8BC(0.25) H8BD(0.25) H10A(0.75) H10B(0.75)
 H10C(0.25) H10D(0.25) C9(0.75) H9A(0.75) H9B(0.75) C9'(0.25) H9'A(0.25)
 H9'B(0.25)
4.a Ternary CH refined with riding coordinates:
 C12(H12)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8AA,H8AB), C8(H8BC,H8BD), C10(H10A,H10B), C10(H10C,H10D), C11(H11A,H11B),
 C14(H14A,H14B), C15(H15A,H15B), C9(H9A,H9B), C9'(H9'A,H9'B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4)
4.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              12025
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-11-08
_olex2_submission_special_instructions 'No special instructions were received'