Au(i)-catalyzed synthesis of 8-oxabicyclo[3.2.1]oct-2-enes and 9-oxabicyclo[3.3.1]nona-2,6-dienes from enynol via oxonium/Prins-type cyclization.
Vandavasi, Jaya Kishore; Hu, Wan-Ping; Boominathan, Siva Senthil Kumar; Guo, Bing-Chun; Hsiao, Cheng-Tien; Wang, Jeh-Jeng; Chemical communications (Cambridge, England) 51 (2015) 12435–12438; doi:10.1039/c5cc02847g

data_7117576
_publ_section_title
;
 Au(i)-catalyzed synthesis of 8-oxabicyclo[3.2.1]oct-2-enes and
 9-oxabicyclo[3.3.1]nona-2,6-dienes from enynol via oxonium/Prins-type
 cyclization.
;
_journal_issue                   62
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12435
_journal_page_last               12438
_journal_paper_doi               10.1039/c5cc02847g
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C22 H22 O'
_chemical_formula_sum            'C22 H22 O'
_chemical_formula_weight         302.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-04-03 deposited with the CCDC.
2015-06-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.856(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.8889(10)
_cell_length_b                   5.8024(3)
_cell_length_c                   15.1560(8)
_cell_measurement_reflns_used    1577
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.9520
_cell_measurement_theta_min      3.9370
_cell_volume                     1652.44(15)
_computing_cell_refinement
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_collection
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7756
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.43
_diffrn_reflns_theta_min         3.01
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+0.3550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1470
_reflns_number_gt                2668
_reflns_number_total             3864
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc02847g2.cif
_cod_data_source_block           bc111173
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7117576