A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes.
Guo, Jia; Peng, Xiaoshi; Wang, Xiaoyu; Xie, Fukai; Zhang, Xinhang; Liang, Guoduan; Sun, Zenghui; Liu, Yongxiang; Cheng, Maosheng; Liu, Yang; Organic & biomolecular chemistry 16 (2018) 9147–9151; doi:10.1039/c8ob02582g

data_7156575
_publ_section_title
;
 A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy
 for 2-aryl indenones from 1,5-enynes.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9147
_journal_page_last               9151
_journal_paper_doi               10.1039/c8ob02582g
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C17 H11 F O3'
_chemical_formula_sum            'C17 H11 F O3'
_chemical_formula_weight         282.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-07-29
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_audit_update_record
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2016-02-02 deposited with the CCDC.
2018-11-14 downloaded from the CCDC.
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.778(3)
_cell_length_b                   5.9149(9)
_cell_length_c                   29.159(5)
_cell_measurement_reflns_used    613
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      22.1260
_cell_measurement_theta_min      4.2330
_cell_volume                     2548.8(8)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
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  1 omega  -50.00   52.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -19.0000    0.0000 102

  2 omega  -13.00   13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6392  -99.0000 -180.0000 26
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_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
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_diffrn_orient_matrix_UB_11      -0.0463646000
_diffrn_orient_matrix_UB_12      -0.0120294000
_diffrn_orient_matrix_UB_13      0.0058724000
_diffrn_orient_matrix_UB_21      -0.0108612000
_diffrn_orient_matrix_UB_22      -0.0166136000
_diffrn_orient_matrix_UB_23      -0.0234595000
_diffrn_orient_matrix_UB_31      0.0061983000
_diffrn_orient_matrix_UB_32      -0.1180387000
_diffrn_orient_matrix_UB_33      0.0027145000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1222
_diffrn_reflns_av_unetI/netI     0.1853
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
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_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            7133
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.011
_diffrn_reflns_theta_min         3.091
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.494
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_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_parameters     191
_refine_ls_number_reflns         2496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.2018
_refine_ls_R_factor_gt           0.0801
_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^)+(0.0339P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                1032
_reflns_number_total             2496
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02582g2.cif
_cod_data_source_block           exp_5652
_cod_depositor_comments          'Adding full bibliography for 7156575.cif.'
_cod_database_code               7156575
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C17 H17 O3 F1'
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.989
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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:
 C5(H5), C6(H6), C8(H8), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              51519
_shelx_hkl_checksum              27659
_olex2_submission_special_instructions 'No special instructions were received'