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_7119630
_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         'C16 H16 O2'
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29
_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     direct
_audit_creation_date             2016-12-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2016-12-11 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                93.807(5)
_cell_angle_beta                 110.400(5)
_cell_angle_gamma                92.911(5)
_cell_formula_units_Z            2
_cell_length_a                   7.5822(4)
_cell_length_b                   8.8509(5)
_cell_length_c                   10.0505(6)
_cell_measurement_reflns_used    2022
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      74.0830
_cell_measurement_theta_min      6.2380
_cell_volume                     628.81(7)
_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 0.9836
_diffrn_measured_fraction_theta_max 0.9419
_diffrn_measurement_details
;
  1 omega  -50.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9538   38.0000   30.0000 83

  2 omega  -69.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9538   77.0000 -120.0000 103

  3 omega  -73.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9538   77.0000  120.0000 102

  4 omega   62.00  167.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826   15.0000   90.0000 105

  5 omega  108.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  125.0000  -30.0000 69

  6 omega   81.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826   30.0000  -30.0000 97

  7 omega   60.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -77.0000 -120.0000 74

  8 omega   43.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -30.0000   60.0000 44

  9 omega   36.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -61.0000   60.0000 90

 10 omega   48.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826 -125.0000   90.0000 71

 11 omega   36.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -45.0000  -60.0000 49

 12 omega   42.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -45.0000 -180.0000 51
;
_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      0.0004652000
_diffrn_orient_matrix_UB_12      -0.1608855000
_diffrn_orient_matrix_UB_13      -0.0684680000
_diffrn_orient_matrix_UB_21      0.0626633000
_diffrn_orient_matrix_UB_22      -0.0604112000
_diffrn_orient_matrix_UB_23      0.1483809000
_diffrn_orient_matrix_UB_31      -0.2082331000
_diffrn_orient_matrix_UB_32      -0.0329857000
_diffrn_orient_matrix_UB_33      -0.0160620000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3341
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         6.247
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43658
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0668P)^2^+0.2704P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1990
_reflns_number_total             2180
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc00218a2.cif
_cod_data_source_block           exp_477
_cod_depositor_comments
'Adding full bibliography for 7119630--7119632.cif.'
_cod_original_cell_volume        628.80(6)
_cod_database_code               7119630
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 98.36
_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:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'