Evidence for Heterolytic Cleavage of a Cyclic Oxonium Ylide: Implications for the Mechanism of the Stevens [1,2]-Shift
Hosseini, Seyedeh Nargess; Johnston, Jeffrey R.; West, Frederick G.; Chemical Communications  (2017) –; doi:10.1039/C7CC07716E

data_7120854
_publ_section_title
;
 Evidence for Heterolytic Cleavage of a Cyclic Oxonium Ylide: Implications
 for the Mechanism of the Stevens [1,2]-Shift
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C7CC07716E
_journal_year                    2017
_chemical_formula_moiety         'C14 H18 O4'
_chemical_formula_sum            'C14 H18 O4'
_chemical_formula_weight         250.28
_chemical_name_systematic
'3-methoxy-3-(2-methoxy-3-phenylcyclopropyl)propanoic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-09-29 deposited with the CCDC.
2017-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.9892(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.3677(6)
_cell_length_b                   38.144(3)
_cell_length_c                   8.4959(6)
_cell_measurement_reflns_used    8257
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      2.43
_cell_volume                     2711.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXD (Schneider & Sheldrick, 2002)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23903
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.136
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9076
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate, n-hexane'
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.362
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         6195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0525P)^2^+1.4568P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1354
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4698
_reflns_number_total             6195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc07716e2.cif
_cod_data_source_block           SNH-05-190
_cod_database_code               7120854
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           2013-3
_shelx_res_checksum              49677