Cu-catalyzed intramolecular aryl-etherification reactions of alkoxyl alkynes with diaryliodonium salts via cleavage of a stable C-O bond
Jing Chen; Chao Chen; Junjie Chen; Guohua Wang; Hongmei Qu; Chem.Commun. 51 (2015) 1356–; doi:10.1039/C4cc08363F

data_7116346
_publ_section_title
;
 Cu-catalyzed intramolecular aryl-etherification reactions of alkoxyl
 alkynes with diaryliodonium salts via cleavage of a stable C-O bond
;
_journal_name_full               Chem.Commun.
_journal_page_first              1356
_journal_paper_doi               10.1039/C4cc08363F
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C17 H15 Br O'
_chemical_formula_sum            'C17 H15 Br O'
_chemical_formula_weight         315.20
_chemical_melting_point          93.4(6)
_chemical_name_systematic        6-(4-bromophenyl)-5-phenyl-3,4-dihydro-2H-pyran
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
;
2014-08-15 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.05(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7276(19)
_cell_length_b                   18.038(7)
_cell_length_c                   13.687(5)
_cell_measurement_reflns_used    42
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      12.65
_cell_measurement_theta_min      5.59
_cell_volume                     1392.4(9)
_computing_cell_refinement       'XSCANS (Bruker, 1997)'
_computing_data_collection       'XSCANS (Bruker, 1997)'
_computing_data_reduction        'XSCANS (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0876
_diffrn_reflns_av_sigmaI/netI    0.0870
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3563
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.941
_exptl_absorpt_correction_T_max  0.3721
_exptl_absorpt_correction_T_min  0.1671
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'North, et al., 1968'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.250
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.250
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0636
_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^)+(0.0010P)^2^+2.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                1682
_reflns_number_total             2542
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            c4cc08363f2.cif
_cod_data_source_block           chenc-28
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '92.8-94.1' was changed to '93.4(6)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7116346