Regioselective Hydrogenolysis of Donor-Acceptor Cyclopropanes with Zn-AcOH Reductive System.
Ivanov, Konstantin L.; Villemson, Elena V.; Latyshev, Gennadij V.; Bezzubov, Stanislav I.; Majouga, Alexander G.; Melnikov, Mikhail Ya; Budynina, Ekaterina M.; The Journal of organic chemistry 82 (2017) 9537–9549; doi:10.1021/acs.joc.7b01549

data_4033064
_publ_contact_author             'Ekaterina Budynina'
_publ_section_title
;
 Regioselective Hydrogenolysis of Donor-Acceptor Cyclopropanes with
 Zn-AcOH Reductive System.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9537
_journal_page_last               9549
_journal_paper_doi               10.1021/acs.joc.7b01549
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C13 H14 O5'
_chemical_formula_sum            'C13 H14 O5'
_chemical_formula_weight         250.24
_chemical_melting_point_gt       362
_chemical_melting_point_lt       363
_chemical_name_systematic
;
 Dimethyl 2-(2-hydroxyphenyl)cyclopropane-1,1-dicarboxylate
;
_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   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.8930(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4488(13)
_cell_length_b                   7.0914(6)
_cell_length_c                   12.1819(11)
_cell_measurement_reflns_used    3379
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.351
_cell_measurement_theta_min      2.840
_cell_volume                     1239.16(19)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       '<i>APEX2</i> (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11506
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.840
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       nugget
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_transmission_factor_max   0.97
_exptl_transmission_factor_min   0.95
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0439P)^2^+0.3206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2477
_reflns_number_total             2981
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01549_si_002.cif
_cod_data_source_block           az5154
_cod_database_code               4033064
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.970
_shelx_res_checksum              17404
_shelx_hkl_checksum              92167