Lewis Acid Catalyzed Nucleophilic Ring Opening and 1,3-Bisfunctionalization of Donor-Acceptor Cyclopropanes with Hydroperoxides: Access to Highly Functionalized Peroxy/(α-Heteroatom Substituted)Peroxy Compounds.
Singh, Kuldeep; Bera, Tishyasoumya; Jaiswal, Vandana; Biswas, Subrata; Mondal, Biplab; Das, Dinabandhu; Saha, Jaideep; The Journal of organic chemistry 84 (2019) 710–725; doi:10.1021/acs.joc.8b02561

data_4036022
_publ_section_title
;
 Lewis Acid Catalyzed Nucleophilic Ring Opening and
 1,3-Bisfunctionalization of Donor-Acceptor Cyclopropanes with
 Hydroperoxides: Access to Highly Functionalized Peroxy/(\a-Heteroatom
 Substituted)Peroxy Compounds.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              710
_journal_page_last               725
_journal_paper_doi               10.1021/acs.joc.8b02561
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C18 H25 Cl O6'
_chemical_formula_sum            'C18 H25 Cl O6'
_chemical_formula_weight         372.83
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                85.484(2)
_cell_angle_beta                 84.662(2)
_cell_angle_gamma                80.436(2)
_cell_formula_units_Z            2
_cell_length_a                   6.1209(5)
_cell_length_b                   8.3258(6)
_cell_length_c                   19.4643(15)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.64
_cell_volume                     971.87(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'X-Seed (Barbour 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018 (Sheldrick, 2015)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-III CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30535
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.348
_diffrn_reflns_theta_min         2.637
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.058(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0447P)^2^+0.2668P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4045
_reflns_number_total             4808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02561_si_002.cif
_cod_data_source_block           TSB226
_cod_database_code               4036022
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.911
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              39710
_shelx_hkl_checksum              34343