Combined Photoredox and Lewis Acid Catalyzed α-Hydroxyalkylation of Cyclic Ethers with Aromatic Ketones.
Reckenthäler, Melissa; Neudörfl, Jörg-M; Zorlu, Elif; Griesbeck, Axel G.; The Journal of organic chemistry 81 (2016) 7211–7216; doi:10.1021/acs.joc.6b01085

data_4036963
_publ_section_title
;
 Combined Photoredox and Lewis Acid Catalyzed \a-Hydroxyalkylation of
 Cyclic Ethers with Aromatic Ketones.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7211
_journal_page_last               7216
_journal_paper_doi               10.1021/acs.joc.6b01085
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C13 H18 O2'
_chemical_formula_sum            'C13 H18 O2'
_chemical_formula_weight         206.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 99.6120(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.6683(4)
_cell_length_b                   5.68680(10)
_cell_length_c                   25.2204(6)
_cell_measurement_reflns_used    11998
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.139
_cell_measurement_theta_min      3.555
_cell_volume                     2215.65(9)
_computing_cell_refinement       'Bruker APEX 2'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker APEX 2'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXt  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            11998
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.139
_diffrn_reflns_theta_min         3.555
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0079(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0588P)^2^+1.8690P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2120
_reflns_number_total             2151
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01085_si_003.cif
_cod_data_source_block           mr-ez21
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4036963
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.882
_shelx_estimated_absorpt_t_max   0.909
_shelx_res_checksum              48397
_shelx_hkl_checksum              46397