Catalytic Ring Expansions of Cyclic Alcohols Enabled by Proton-Coupled Electron Transfer.
Zhao, Kuo; Yamashita, Kenji; Carpenter, Joseph E.; Sherwood, Trevor C.; Ewing, William R.; Cheng, Peter T. W.; Knowles, Robert R.; Journal of the American Chemical Society 141 (2019) 8752–8757; doi:10.1021/jacs.9b03973

data_4127579
_publ_section_title
;
 Catalytic Ring Expansions of Cyclic Alcohols Enabled by Proton-Coupled
 Electron Transfer.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8752
_journal_page_last               8757
_journal_paper_doi               10.1021/jacs.9b03973
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H25 N O3'
_chemical_formula_weight         255.35
_chemical_name_common            KZ3
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 98.4333(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.67270(10)
_cell_length_b                   17.8456(4)
_cell_length_c                   12.3622(3)
_cell_measurement_reflns_used    8462
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      68.5041
_cell_measurement_theta_min      3.6145
_cell_volume                     1456.15(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10993
_diffrn_reflns_theta_full        66.56
_diffrn_reflns_theta_max         66.56
_diffrn_reflns_theta_min         4.96
_diffrn_source                   'I\mS microfocus source'
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular prism'
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.164
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.130
_refine_ls_abs_structure_details
;
 Flack x determined using 1174 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0222
_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^)+(0.0272P)^2^+0.4169P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0548
_refine_ls_wR_factor_ref         0.0549
_reflns_number_gt                2477
_reflns_number_total             2494
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b03973_si_003.cif
_cod_data_source_block           PDJKZ3
_cod_database_code               4127579
_shelx_res_checksum              9921
_shelx_hkl_checksum              3309