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_4029062
_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         'C19 H15 Cl O2'
_chemical_formula_sum            'C19 H15 Cl O2'
_chemical_formula_weight         310.76
_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     direct
_audit_creation_date             2013-12-11
_audit_creation_method
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Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
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_cell_angle_alpha                90
_cell_angle_beta                 95.309(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9699(3)
_cell_length_b                   8.9969(6)
_cell_length_c                   28.9795(15)
_cell_measurement_reflns_used    1795
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0140
_cell_measurement_theta_min      3.6130
_cell_volume                     1549.83(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0643674000
_diffrn_orient_matrix_UB_12      -0.0654625000
_diffrn_orient_matrix_UB_13      0.0021867000
_diffrn_orient_matrix_UB_21      -0.0110036000
_diffrn_orient_matrix_UB_22      -0.0083319000
_diffrn_orient_matrix_UB_23      -0.0244423000
_diffrn_orient_matrix_UB_31      0.0998845000
_diffrn_orient_matrix_UB_32      -0.0431227000
_diffrn_orient_matrix_UB_33      0.0014337000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            5957
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.620
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0506
_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^)+(0.0541P)^2^+0.1548P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1376
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2151
_reflns_number_total             3045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wanglj1126_1.cif
_cod_data_source_block           wanglj1126_1
_cod_original_cell_volume        1549.81(16)
_cod_database_code               4029062
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.41
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              73660
_shelx_hkl_checksum              19072