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_1547740
_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         'C18 H13 F O2'
_chemical_formula_sum            'C18 H13 F O2'
_chemical_formula_weight         280.28
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-11-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
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_cell_length_b                   7.3743(3)
_cell_length_c                   11.6885(5)
_cell_measurement_reflns_used    3264
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.1940
_cell_measurement_theta_min      5.6020
_cell_volume                     1354.46(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
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_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 0.998
_diffrn_measured_fraction_theta_max 0.967
_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    -70.00  23.00   1.00    1.00    --  -40.46  57.00-120.00   93
  2  \w    -72.00 -37.00   1.00    1.00    --  -40.46  77.00   0.00   35
  3  \w    -67.00  28.00   1.00    1.00    --  -40.46  37.00 150.00   95
  4  \w     45.00  85.00   1.00    1.00    --  107.48-111.00-120.00   40
  5  \w     41.00 105.00   1.00    1.00    --  107.48 -94.00   0.00   64
  6  \w     42.00 128.00   1.00    1.00    --  107.48 -45.00  60.00   86
  7  \w    149.00 177.00   1.00    1.00    --  107.48  61.00 -30.00   28
  8  \w     78.00 129.00   1.00    1.00    --  107.48  61.00 -30.00   51
  9  \w     82.00 167.00   1.00    1.00    --  107.48  45.00-120.00   85
 10  \w     30.00  97.00   1.00    1.00    --  107.48 -77.00  30.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0214685000
_diffrn_orient_matrix_UB_12      0.0661660000
_diffrn_orient_matrix_UB_13      0.1149145000
_diffrn_orient_matrix_UB_21      0.0907950000
_diffrn_orient_matrix_UB_22      -0.0481561000
_diffrn_orient_matrix_UB_23      0.0678380000
_diffrn_orient_matrix_UB_31      0.0300969000
_diffrn_orient_matrix_UB_32      0.1922080000
_diffrn_orient_matrix_UB_33      -0.0226035000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4809
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.480
_diffrn_reflns_theta_min         5.631
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40170
_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    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         2639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0987P)^2^+0.2893P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1499
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2411
_reflns_number_total             2639
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02834_si_003.cif
_cod_data_source_block           01_2
_cod_depositor_comments
'Adding full bibliography for 1547739--1547741.cif.'
_cod_original_cell_volume        1354.46(9)
_cod_database_code               1547740
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.895
_shelx_estimated_absorpt_t_min   0.855
_reflns_odcompleteness_completeness 99.89
_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:
 C7(H7), C13(H13), C4(H4), C17(H17), C8(H8), C11(H11), C10(H10), C14(H14),
 C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 2.547
_oxdiff_exptl_absorpt_empirical_full_min 0.629