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_7121191
_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         'C21 H15 Br O5'
_chemical_formula_sum            'C21 H15 Br O5'
_chemical_formula_weight         427.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-11-20 deposited with the CCDC.
2018-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                70.653(2)
_cell_angle_beta                 81.146(2)
_cell_angle_gamma                88.316(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0941(2)
_cell_length_b                   9.6765(2)
_cell_length_c                   11.9451(3)
_cell_measurement_reflns_used    7135
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.8510
_cell_measurement_theta_min      3.9320
_cell_volume                     871.99(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.960
_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    -31.00  19.00   0.50    0.50    --    0.00 -57.00  90.00  100
  2  \w    -30.00   5.00   0.50    0.50    --    0.00 -57.00-150.00   70
  3  \w    -78.00 -47.00   0.50    0.50    --    0.00 -57.00-180.00   62
  4  \w    -89.00 -41.00   0.50    0.50    --    0.00 -57.00  90.00   96
  5  \w     31.00  75.00   0.50    0.50    --    0.00  19.00  60.00   88
  6  \w    -17.00  20.00   0.50    0.50    --    0.00  19.00  60.00   74
  7  \w     52.00 125.00   0.50    0.50    --   95.20 -82.00 -30.00  146
  8  \w      7.00  41.00   0.50    0.50    --   95.20 -30.00-150.00   68
  9  \w    112.00 147.00   0.50    0.50    --   95.20   0.00  60.00   70
 10  \w     64.00 115.00   0.50    0.50    --   95.20 -61.00  60.00  102
 11  \w     85.00 122.00   0.50    0.50    --   95.20 -82.00-120.00   74
 12  \w     10.00  36.00   0.50    0.50    --   95.20 -82.00 -30.00   52
 13  \w     25.00 111.00   0.50    0.50    --   95.20 -61.00-180.00  172
 14  \w      7.00  32.00   0.50    0.50    --   95.20 -82.00  60.00   50
 15  \w     29.00  86.00   0.50    0.50    --   95.20 -77.00   0.00  114
 16  \w     11.00  36.00   0.50    0.50    --   95.20 -15.00  90.00   50
 17  \w     28.00 114.00   0.50    0.50    --   95.20 -45.00   0.00  172
 18  \w     85.00 127.00   0.50    0.50    --   95.20 -82.00  60.00   84
 19  \w     45.00 117.00   0.50    0.50    --   95.20 -15.00  90.00  144
 20  \w     19.00  56.00   0.50    0.50    --   95.20 -61.00  60.00   74
 21  \w     49.00  74.00   0.50    0.50    --   95.20 -82.00  60.00   50
 22  \w      6.00 112.00   0.50    0.50    --   95.20 -30.00-120.00  212
 23  \w    150.00 181.00   0.50    0.50    --   95.20   0.00  60.00   62
 24  \w      6.00 104.00   0.50    0.50    --   95.20   0.00  60.00  196
 25  \w     61.00 121.00   0.50    0.50    --   95.20 -82.00 174.72  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0943786000
_diffrn_orient_matrix_UB_12      -0.0804580000
_diffrn_orient_matrix_UB_13      0.1049075000
_diffrn_orient_matrix_UB_21      -0.0396932000
_diffrn_orient_matrix_UB_22      0.1240990000
_diffrn_orient_matrix_UB_23      0.0533767000
_diffrn_orient_matrix_UB_31      -0.1632242000
_diffrn_orient_matrix_UB_32      -0.0813184000
_diffrn_orient_matrix_UB_33      0.0726393000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8346
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.462
_diffrn_reflns_theta_min         3.969
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.490
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0460P)^2^+0.6820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3290
_reflns_number_total             3413
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc09786g2.cif
_cod_data_source_block           180-2
_cod_depositor_comments
'Adding full bibliography for 7121190--7121192.cif.'
_cod_database_code               7121191
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.700
_shelx_estimated_absorpt_t_min   0.572
_reflns_odcompleteness_completeness 99.68
_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:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C14(H14), C3(H3), C17(H17), C15(H15), C2(H2), C16(H16)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_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 1.851
_oxdiff_exptl_absorpt_empirical_full_min 0.574