Electrochemical chlorination of least hindered tertiary and benzylic C(sp3)–H bonds
Zhao, Jianyou; Zhang, Jiatai; Fang, Pengkai; Wu, Jintao; Wang, Fan; Liu, Zhong-Quan; Green Chemistry 26 (2024) 507–512; doi:10.1039/D3GC03849A

data_7247931
_publ_section_title
;
 Electrochemical chlorination of least hindered tertiary and benzylic
 C(sp3)--H bonds
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              507
_journal_page_last               512
_journal_paper_doi               10.1039/D3GC03849A
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H21 Cl O5'
_chemical_formula_sum            'C15 H21 Cl O5'
_chemical_formula_weight         316.77
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc299bdc
_audit_creation_date             2021-10-18
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2021-11-24 deposited with the CCDC.	2023-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.343
_cell_length_b                   9.959
_cell_length_c                   23.828
_cell_measurement_reflns_used    6718
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      53.73
_cell_measurement_theta_min      4.19
_cell_volume                     1505.213
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11099
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.924
_diffrn_reflns_theta_min         4.186
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.594
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.4793
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1314 before and 0.0801 after correction.
The Ratio of minimum to maximum transmission is 0.6386.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 856 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0492P)^2^+0.1363P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1011
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                2383
_reflns_number_total             2714
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03849a2.cif
_cod_data_source_block           20211014li_xiejin_lm2_1_0m
_cod_depositor_comments          'Adding full bibliography for 7247931.cif.'
_cod_original_cell_volume        1505.3
_cod_database_code               7247931
_shelx_shelxl_version_number     2018/3
_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.a Ternary CH refined with riding coordinates:
 C5(H5), C10(H10), C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C8(H8A,H8B), C12(H12A,H12B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              61607
_olex2_submission_special_instructions 'No special instructions were received'