Gold-catalyzed tandem [3,3]-propargyl ester rearrangement leading to (E)-1H-inden-1-ones.
Wang, Li-Jing; Zhu, Hai-Tao; Wang, An-Qi; Qiu, Yi-Feng; Liu, Xue-Yuan; Liang, Yong-Min; The Journal of organic chemistry 79 (2014) 204–212; doi:10.1021/jo402396h

data_4029063
_publ_section_title
;
 Gold-catalyzed tandem [3,3]-propargyl ester rearrangement leading to
 (E)-1H-inden-1-ones.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              204
_journal_page_last               212
_journal_paper_doi               10.1021/jo402396h
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C24 H18 O2'
_chemical_formula_sum            'C24 H18 O2'
_chemical_formula_weight         338.38
_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
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-11-27
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4715)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.27(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.712(3)
_cell_length_b                   5.8398(14)
_cell_length_c                   20.996(6)
_cell_measurement_reflns_used    654
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.8510
_cell_measurement_theta_min      3.7680
_cell_volume                     1740.2(8)
_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, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9911
_diffrn_measured_fraction_theta_max 0.8744
_diffrn_measurement_details
;
  1 omega  -37.00   14.00   1.5000   38.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -77.0000 -120.0000 34

  2 omega   -8.00   19.00   1.5000   38.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -99.0000  -30.0000 18

  3 omega   44.00  104.00   1.5000   38.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000  -90.0000 40

  4 omega  -28.00   -1.00   1.5000   38.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -77.0000 -180.0000 18

  5 omega   40.00   88.00   1.5000   38.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   77.0000 -150.0000 32

  6 omega   36.00   96.00   1.5000   38.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000   90.0000 40
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0452869000
_diffrn_orient_matrix_UB_12      -0.0487929000
_diffrn_orient_matrix_UB_13      0.0044199000
_diffrn_orient_matrix_UB_21      0.0060249000
_diffrn_orient_matrix_UB_22      0.0616520000
_diffrn_orient_matrix_UB_23      -0.0277322000
_diffrn_orient_matrix_UB_31      0.0201356000
_diffrn_orient_matrix_UB_32      0.0927696000
_diffrn_orient_matrix_UB_33      0.0208454000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0998
_diffrn_reflns_av_unetI/netI     0.1397
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7226
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07127
_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_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0047(11)
_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   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.1882
_refine_ls_R_factor_gt           0.0755
_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^)+(0.0433P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1987
_reflns_number_gt                1295
_reflns_number_total             3399
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            wanglj1126_2.cif
_cod_data_source_block           wanglj1126_2
_cod_database_code               4029063
_reflns_odcompleteness_completeness 99.11
_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
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C1C(H1C)
;