Cu(ii)-mediated direct intramolecular cyclopropanation of distal olefinic acetate: access to cyclopropane-fused γ-lactones.
Wang, Yulong; Shen, Shenyu; He, Chonglong; Zhou, Youkang; Zhang, Keyuan; Rao, Bin; Han, Tian; Su, Yaqiong; Duan, Xin-Hua; Liu, Le; Chemical science 14 (2023) 6663–6668; doi:10.1039/d3sc01752d

data_1569213
_publ_section_title
;
 Cu(ii)-mediated direct intramolecular cyclopropanation of distal olefinic
 acetate: access to cyclopropane-fused &#x3b3;-lactones.
;
_journal_issue                   24
_journal_name_full               'Chemical science'
_journal_page_first              6663
_journal_page_last               6668
_journal_paper_doi               10.1039/d3sc01752d
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C17 H14 O4 S'
_chemical_formula_sum            'C17 H14 O4 S'
_chemical_formula_weight         314.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2fnkm9
_audit_creation_date             2022-07-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-04-05 deposited with the CCDC.	2023-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.679(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8755(13)
_cell_length_b                   7.1896(5)
_cell_length_c                   14.6846(13)
_cell_measurement_reflns_used    5162
_cell_measurement_temperature    300
_cell_measurement_theta_max      25.71
_cell_measurement_theta_min      2.78
_cell_volume                     1461.9(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20618
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.381
_diffrn_reflns_theta_min         1.958
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6830
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0809 before and 0.0607 after correction.
The Ratio of minimum to maximum transmission is 0.9163.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0432P)^2^+0.5568P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2242
_reflns_number_total             2974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01752d2.cif
_cod_data_source_block           mo_0721wyl_0m
_cod_depositor_comments          'Adding full bibliography for 1569213.cif.'
_cod_database_code               1569213
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.871
_shelx_estimated_absorpt_t_min   0.797
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_shelx_res_checksum              87631
_shelx_hkl_checksum              47910
_olex2_submission_special_instructions 'No special instructions were received'