Catalyst-free benzylic C(sp3)–H cross-coupling with organotrifluoroborates enabled by electrochemistry
Li, Chao; Ding, Ran; Guo, Heng-Yi; Xia, Shuang; Shu, Lei; Wang, Pei-Long; Li, Hongji; Green Chemistry 24 (2022) 7883–7888; doi:10.1039/D2GC02204D

data_7245475
_publ_section_title
;
 Catalyst-free benzylic C(sp3)--H cross-coupling with
 organotrifluoroborates enabled by electrochemistry
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              7883
_journal_page_last               7888
_journal_paper_doi               10.1039/D2GC02204D
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C20 H16 O'
_chemical_formula_sum            'C20 H16 O'
_chemical_formula_weight         272.33
_chemical_name_systematic        9-benzyl-9H-xanthene
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2021-10-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2022-03-26 deposited with the CCDC.	2022-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                91.600(12)
_cell_angle_beta                 90.153(12)
_cell_angle_gamma                90.094(13)
_cell_formula_units_Z            4
_cell_length_a                   5.6133(16)
_cell_length_b                   11.125(3)
_cell_length_c                   23.100(6)
_cell_measurement_reflns_used    830
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.26
_cell_measurement_theta_min      3.05
_cell_volume                     1442.0(7)
_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      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            60841
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.656
_diffrn_reflns_theta_min         2.507
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0665 before and 0.0554 after correction.
The Ratio of minimum to maximum transmission is 0.9670.
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    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0600P)^2^+0.1990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1355
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4669
_reflns_number_total             6682
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc02204d2.cif
_cod_data_source_block           t1
_cod_depositor_comments          'Adding full bibliography for 7245475.cif.'
_cod_database_code               7245475
_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:
 C00C(H00C), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C00Y(H00A,H00B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00I(H00I), C00K(H00K), C00M(H00M), C00N(H00N), C00P(H00P),
 C00R(H00R), C00U(H00U), C00V(H00V), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6),
 C10(H10), C010(H010), C11(H11), C011(H011), C12(H12), C13(H13), C014(H014),
 C16(H16), C016(H016), C17(H17), C18(H18), C19(H19)
;
_shelx_res_checksum              82499
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'