Selectivity-switchable construction of benzo-fused polycyclic compounds through a gold-catalyzed reaction of enyne-lactone.
Luo, Kui; Zhang, Ling; Jiang, Huanfeng; Chen, Lianfen; Zhu, Shifa; Chemical communications (Cambridge, England) 54 (2018) 1893–1896; doi:10.1039/c7cc09786g

data_7121190
_publ_section_title
;
 Selectivity-switchable construction of benzo-fused polycyclic compounds
 through a gold-catalyzed reaction of enyne-lactone.
;
_journal_issue                   15
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1893
_journal_page_last               1896
_journal_paper_doi               10.1039/c7cc09786g
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C24 H20 O5'
_chemical_formula_sum            'C24 H20 O5'
_chemical_formula_weight         388.40
_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     dual
_audit_creation_date             2017-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_audit_update_record
;
2017-01-09 deposited with the CCDC.
2018-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   9.52631(13)
_cell_length_b                   14.5795(3)
_cell_length_c                   26.9344(4)
_cell_measurement_reflns_used    13244
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4660
_cell_measurement_theta_min      4.4580
_cell_volume                     3740.89(11)
_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    'ShelXT (Sheldrick, 2015)'
_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 0.976
_diffrn_measured_fraction_theta_max 0.964
_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    -73.00  26.00   1.00    1.00    --  -40.73  77.00 -90.00   99
  2  \w      0.00  32.00   1.00    1.00    --  -40.73  37.00-180.00   32
  3  \w    -65.00 -38.00   1.00    1.00    --  -40.73  37.00-180.00   27
  4  \w   -116.00 -29.00   1.00    1.00    --  -40.73 -19.00   0.00   87
  5  \w   -104.00 -16.00   1.00    1.00    --  -40.73 -57.00 120.00   88
  6  \w      4.00  82.00   1.00    1.00    --   40.73 -99.00   0.00   78
  7  \w     35.00 132.00   1.00    1.00    --  106.95 -61.00  30.00   97
  8  \w     77.00 115.00   1.00    1.00    --  106.95-125.00 -30.00   38
  9  \w     74.00 107.00   1.00    1.00    --  106.95 -94.00   0.00   33
 10  \w     35.00 130.00   1.00    1.00    --  106.95 -61.00 -90.00   95
 11  \w     83.00 118.00   1.00    1.00    --  106.95  30.00 -60.00   35
 12  \w    131.00 177.00   1.00    1.00    --  106.95  30.00 -60.00   46
 13  \w     84.00 146.00   1.00    1.00    --  106.95  30.00   0.00   62
 14  \w     48.00 136.00   1.00    1.00    --  106.95 -77.00 150.00   88
 15  \w     84.00  99.00   1.00    1.00    --  106.95-125.00 150.00   15
;
_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      -0.0446338000
_diffrn_orient_matrix_UB_12      -0.0786598000
_diffrn_orient_matrix_UB_13      0.0347636000
_diffrn_orient_matrix_UB_21      0.0303143000
_diffrn_orient_matrix_UB_22      -0.0699032000
_diffrn_orient_matrix_UB_23      -0.0415160000
_diffrn_orient_matrix_UB_31      0.1525137000
_diffrn_orient_matrix_UB_32      -0.0091379000
_diffrn_orient_matrix_UB_33      0.0184212000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            18297
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.508
_diffrn_reflns_theta_min         5.786
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58540
_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    1.379
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0570P)^2^+2.1280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3496
_reflns_number_total             3625
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc09786g2.cif
_cod_data_source_block           lk_57
_cod_depositor_comments
'Adding full bibliography for 7121190--7121192.cif.'
_cod_original_cell_volume        3740.88(10)
_cod_database_code               7121190
_shelx_shelxl_version_number     2014/7
_cell_oxdiff_angle_alpha         89.9931(18)
_cell_oxdiff_angle_beta          89.9958(16)
_cell_oxdiff_angle_gamma         89.9939(18)
_cell_oxdiff_length_a            9.52279(18)
_cell_oxdiff_length_b            14.5848(4)
_cell_oxdiff_length_c            26.9346(5)
_cell_oxdiff_measurement_reflns_used 13244
_cell_oxdiff_volume              3740.88(14)
_shelx_estimated_absorpt_t_max   0.871
_shelx_estimated_absorpt_t_min   0.809
_reflns_odcompleteness_completeness 96.93
_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 Ternary CH refined with riding coordinates:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C6(H6), C4(H4), C20(H20), C18(H18), C5(H5), C16(H16),
 C17(H17), C19(H19)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C22(H22A,H22B,H22C)
;
_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 1.669
_oxdiff_exptl_absorpt_empirical_full_min 0.662