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_1547739
_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         'C17 H14 O5'
_chemical_formula_sum            'C17 H14 O5'
_chemical_formula_weight         298.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.36160(10)
_cell_length_b                   8.77830(10)
_cell_length_c                   19.3853(3)
_cell_measurement_reflns_used    3274
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2150
_cell_measurement_theta_min      5.5140
_cell_volume                     1422.89(3)
_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    'ShelXS (Sheldrick, 2008)'
_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 0.9987
_diffrn_measured_fraction_theta_max 0.8114
_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    -64.00  -9.00   1.00    1.00    --  -40.73  57.00 150.00   55
  2  \w     -6.00  21.00   1.00    1.00    --  -40.73  57.00 150.00   27
  3  \w    -43.00  -2.00   1.00    1.00    --  -40.73 125.00   0.00   41
  4  \w     81.00 169.00   1.00    1.00    --  106.95  61.00 -60.00   88
  5  \w     98.00 149.00   1.00    1.00    --  106.95 125.00  30.00   51
  6  \w    112.00 151.00   1.00    1.00    --  106.95 125.00  90.00   39
  7  \w     84.00 175.00   1.00    1.00    --  106.95  30.00-150.00   91
  8  \w     38.00  86.00   1.00    1.00    --   40.73-125.00 -60.00   48
;
_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      0.0897170000
_diffrn_orient_matrix_UB_12      0.0591109000
_diffrn_orient_matrix_UB_13      -0.0640174000
_diffrn_orient_matrix_UB_21      -0.0595982000
_diffrn_orient_matrix_UB_22      0.1624455000
_diffrn_orient_matrix_UB_23      0.0151420000
_diffrn_orient_matrix_UB_31      0.1494602000
_diffrn_orient_matrix_UB_32      0.0297906000
_diffrn_orient_matrix_UB_33      0.0446670000
_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  0.0153
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3695
_diffrn_reflns_point_group_measured_fraction_full 0.851
_diffrn_reflns_point_group_measured_fraction_max 0.811
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.659
_diffrn_reflns_theta_min         4.562
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53671
_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    1.392
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 699 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(10)
_refine_ls_extinction_coef       0.0172(11)
_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   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0294
_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^)+(0.0470P)^2^+0.2160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0804
_reflns_Friedel_coverage         0.441
_reflns_Friedel_fraction_full    0.642
_reflns_Friedel_fraction_max     0.593
_reflns_number_gt                2311
_reflns_number_total             2325
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02834_si_004.cif
_cod_data_source_block           02
_cod_depositor_comments
'Adding full bibliography for 1547739--1547741.cif.'
_cod_database_code               1547739
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.783
_reflns_odcompleteness_completeness 99.87
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C4(H4), C5(H5), C10(H10), C13(H13), C12(H12), C11(H11)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              9683
_shelx_hkl_checksum              51771
_shelx_shelxl_version_number     2014/7
_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 1.377
_oxdiff_exptl_absorpt_empirical_full_min 0.667