Gold-Catalyzed Ring Expansion of Enyne-Lactone: Generation and Transformation of 2-Oxoninonium.
Luo, Kui; Cao, Tongxiang; Jiang, Huanfeng; Chen, Lianfen; Zhu, Shifa; Organic letters 19 (2017) 5856–5859; doi:10.1021/acs.orglett.7b02834

data_1547741
_publ_section_title
;
 Gold-Catalyzed Ring Expansion of Enyne-Lactone: Generation and
 Transformation of 2-Oxoninonium.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5856
_journal_page_last               5859
_journal_paper_doi               10.1021/acs.orglett.7b02834
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C22 H18 O6'
_chemical_formula_sum            'C22 H18 O6'
_chemical_formula_weight         378.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-01-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                92.573(5)
_cell_angle_beta                 94.393(5)
_cell_angle_gamma                91.114(5)
_cell_formula_units_Z            2
_cell_length_a                   8.6474(5)
_cell_length_b                   9.0011(6)
_cell_length_c                   11.6253(6)
_cell_measurement_reflns_used    4700
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6010
_cell_measurement_theta_min      6.0810
_cell_volume                     901.06(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.9620
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -62.00  26.00   1.00    1.00    --  -40.73  57.00  30.00   88
  2  \w    -35.00  61.00   1.00    1.00    --   40.73 -77.00 150.00   96
  3  \w     57.00  82.00   1.00    1.00    --   40.73 -99.00  90.00   25
  4  \w     63.00 121.00   1.00    1.00    --  106.95-125.00   0.00   58
  5  \w     63.00 108.00   1.00    1.00    --  106.95 -94.00 120.00   45
  6  \w     38.00 133.00   1.00    1.00    --  106.95 -45.00  30.00   95
  7  \w     82.00 109.00   1.00    1.00    --  106.95  30.00  90.00   27
  8  \w    120.00 166.00   1.00    1.00    --  106.95  61.00 -30.00   46
  9  \w    128.00 154.00   1.00    1.00    --  106.95  61.00 -60.00   26
 10  \w     88.00 114.00   1.00    1.00    --  106.95  30.00-120.00   26
 11  \w     79.00 111.00   1.00    1.00    --  106.95  61.00 -60.00   32
 12  \w     82.00 176.00   1.00    1.00    --  106.95  30.00 -90.00   94
 13  \w     39.00 105.00   1.00    1.00    --  106.95 -94.00  30.00   66
 14  \w     33.00  58.00   1.00    1.00    --  106.95 -94.00 -90.00   25
 15  \w     36.00 130.00   1.00    1.00    --  106.95 -77.00-180.00   94
 16  \w     31.00 132.00   1.00    1.00    --  106.95 -30.00 -90.00  101
 17  \w      5.00  51.00   1.00    1.00    --   40.73 -99.00  90.00   46
 18  \w   -111.00 -13.00   1.00    1.00    --  -40.73 -57.00-120.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0684386000
_diffrn_orient_matrix_UB_12      -0.0544282000
_diffrn_orient_matrix_UB_13      -0.1211620000
_diffrn_orient_matrix_UB_21      0.1085946000
_diffrn_orient_matrix_UB_22      -0.1336579000
_diffrn_orient_matrix_UB_23      0.0034629000
_diffrn_orient_matrix_UB_31      -0.1243632000
_diffrn_orient_matrix_UB_32      -0.0924163000
_diffrn_orient_matrix_UB_33      0.0548697000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5740
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.975
_diffrn_reflns_theta_min         3.818
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.094(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0799P)^2^+0.4542P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1338
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3342
_reflns_number_total             3517
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02834_si_002.cif
_cod_data_source_block           lk
_cod_depositor_comments
'Adding full bibliography for 1547739--1547741.cif.'
_cod_database_code               1547741
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.849
_shelx_estimated_absorpt_t_min   0.773
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C6(H6), C7(H7), C8(H8), C9(H9), C18(H18), C17(H17)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              74649
_shelx_hkl_checksum              70327
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.082
_oxdiff_exptl_absorpt_empirical_full_min 0.623