Gold-catalyzed ring-expansion through acyl migration to afford furan-fused polycyclic compounds.
Zhang, Changyuan; Jiang, Huanfeng; Zhu, Shifa; Chemical communications (Cambridge, England) 53 (2017) 2677–2680; doi:10.1039/c7cc00218a

data_7119631
_publ_section_title
;
 Gold-catalyzed ring-expansion through acyl migration to afford
 furan-fused polycyclic compounds.
;
_journal_issue                   18
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2677
_journal_page_last               2680
_journal_paper_doi               10.1039/c7cc00218a
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C23 H16 O2'
_chemical_formula_sum            'C23 H16 O2'
_chemical_formula_weight         324.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-01-07 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.8686(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.58064(8)
_cell_length_b                   21.6340(3)
_cell_length_c                   13.33275(19)
_cell_measurement_reflns_used    5661
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      74.2420
_cell_measurement_theta_min      4.0740
_cell_volume                     1575.27(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -62.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0788   57.0000  -60.0000 90

  2 omega  -65.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0788   57.0000   60.0000 96

  3 omega -113.00  -17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0788  -57.0000  150.0000 96

  4 omega   35.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -45.0000  -90.0000 61

  5 omega   42.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -30.0000 -180.0000 48

  6 omega   27.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -94.0000  -60.0000 82

  7 omega   52.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826 -125.0000  -90.0000 69

  8 omega   33.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -77.0000   30.0000 108

  9 omega   93.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826   45.0000    0.0000 85

 10 omega   37.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -30.0000   90.0000 54

 11 omega   29.00  155.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -15.0000  -30.0000 126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0102144000
_diffrn_orient_matrix_UB_12      0.0378983000
_diffrn_orient_matrix_UB_13      -0.0968958000
_diffrn_orient_matrix_UB_21      0.0787729000
_diffrn_orient_matrix_UB_22      0.0574802000
_diffrn_orient_matrix_UB_23      0.0668792000
_diffrn_orient_matrix_UB_31      0.2707069000
_diffrn_orient_matrix_UB_32      -0.0180553000
_diffrn_orient_matrix_UB_33      0.0095848000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8094
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         3.956
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0475P)^2^+0.4190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2581
_reflns_number_total             2771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc00218a2.cif
_cod_data_source_block           exp_478
_cod_depositor_comments
'Adding full bibliography for 7119630--7119632.cif.'
_cod_database_code               7119631
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              22608
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'