Electrochemical oxidative C-C bond cleavage of methylenecyclopropanes with alcohols.
Kumar, Rakesh; Dutt, Shiv; Banerjee, Prabal; Chemical communications (Cambridge, England) 60 (2024) 4246–4249; doi:10.1039/d4cc00843j

data_7133004
_publ_section_title
;
 Electrochemical oxidative C-C bond cleavage of methylenecyclopropanes
 with alcohols.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4246
_journal_page_last               4249
_journal_paper_doi               10.1039/d4cc00843j
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C18 H20 O3'
_chemical_formula_sum            'C18 H20 O3'
_chemical_formula_weight         284.34
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-27
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-27 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.978(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.380(12)
_cell_length_b                   5.972(3)
_cell_length_c                   18.656(7)
_cell_measurement_reflns_used    3275
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      3.4
_cell_volume                     3221(2)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17379
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_min         3.449
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs-2016/2
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_description       'Plate Type'
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.045
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.6106
_refine_diff_density_max         0.718
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3275
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0790
_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^)+(0.1251P)^2^+3.8445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2235
_refine_ls_wR_factor_ref         0.2399
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2527
_reflns_number_total             3275
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00843j2.cif
_cod_data_source_block           pb_26_04_138_0m
_cod_original_cell_volume        3222(2)
_cod_database_code               7133004
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C16(H16), C15(H15), C14(H14), C5(H5), C4(H4), C3(H3),
 C2(H2), C1(H1)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              88141
_shelx_fab_checksum              55047
_olex2_submission_special_instructions 'No special instructions were received'