Electrocatalytic synthesis of α,α-gem-dihalide ketones from α-mono-halide ketones and unexpected dimer condensation
Zhou, Bei; He, Yu-Juan; Tao, Yun-Feng; Liu, Lan-Xiang; Hu, Min; Chang, Zu-Hui; Lei, Hong; Lin, Jun; Lin, Tong; Du, Guan-Ben; Green Chemistry 24 (2022) 2859–2870; doi:10.1039/D1GC04584A

data_7244581
_publ_section_title
;
 Electrocatalytic synthesis of \a,\a-gem-dihalide ketones from
 \a-mono-halide ketones and unexpected dimer condensation
;
_journal_issue                   7
_journal_name_full               'Green Chemistry'
_journal_page_first              2859
_journal_page_last               2870
_journal_paper_doi               10.1039/D1GC04584A
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C15 H12 O3'
_chemical_formula_sum            'C15 H12 O3'
_chemical_formula_weight         240.25
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-30 deposited with the CCDC.	2022-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.799(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9535(3)
_cell_length_b                   14.0575(5)
_cell_length_c                   9.4542(3)
_cell_measurement_reflns_used    8248
_cell_measurement_temperature    149.44
_cell_measurement_theta_max      74.548
_cell_measurement_theta_min      4.940
_cell_volume                     1189.83(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      149.44
_diffrn_measured_fraction_theta_full 0.998
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1052
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19949
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.084
_diffrn_reflns_theta_min         4.940
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.3884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1548 before and 0.1145 after correction. The Ratio of minimum to maximum transmission is 0.5153. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       0.0119(18)
_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   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0669
_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^)+(0.0849P)^2^+0.6458P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1745
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1848
_reflns_number_total             2335
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc04584a2.cif
_cod_data_source_block           cu_1217_9_0m
_cod_depositor_comments          'Adding full bibliography for 7244581.cif.'
_cod_database_code               7244581
_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
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_shelx_res_checksum              35637
_olex2_submission_special_instructions 'No special instructions were received'