Visible-light-induced 1,3-difunctionalization of allylboronic esters enabled by a 1,2-boron shift
Xiang, Panjie; Sun, Kai; Shi, Anzai; An, Jiangzhen; Chen, Xiaolan; Qu, Lingbo; Yu, Bing; Green Chemistry 27 (2025) 1820–1827; doi:10.1039/D4GC06330A

data_7249742
_publ_section_title
;
 Visible-light-induced 1,3-difunctionalization of allylboronic esters
 enabled by a 1,2-boron shift
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              1820
_journal_page_last               1827
_journal_paper_doi               10.1039/D4GC06330A
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C19 H28 B N O4 S'
_chemical_formula_sum            'C19 H28 B N O4 S'
_chemical_formula_weight         377.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2022-06-07
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-07-18 deposited with the CCDC.	2025-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                84.420(3)
_cell_angle_beta                 63.871(3)
_cell_angle_gamma                87.806(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7822(7)
_cell_length_b                   10.6868(8)
_cell_length_c                   11.0049(8)
_cell_measurement_reflns_used    6241
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.33
_cell_volume                     1027.98(13)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9958
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16617
_diffrn_reflns_theta_full        27.5143
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5977
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1317 before and 0.0696 after correction.
The Ratio of minimum to maximum transmission is 0.8016.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2189
_exptl_crystal_description       needle
_exptl_crystal_F_000             404.4371
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.5365
_refine_diff_density_min         -0.8197
_refine_diff_density_rms         0.1384
_refine_ls_d_res_high            0.7692
_refine_ls_d_res_low             10.6360
_refine_ls_goodness_of_fit_ref   1.0581
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0581
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0811
_refine_ls_shift/su_max          0.0108
_refine_ls_shift/su_mean         0.0008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1344P)^2^+0.8366P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2334
_refine_ls_wR_factor_ref         0.2616
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3533
_reflns_number_total             4702
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4gc06330a2.cif
_cod_data_source_block           a_a
_cod_depositor_comments          'Adding full bibliography for 7249742.cif.'
_cod_database_code               7249742
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C6(H6a,H6b,H6c), C5(H5a,H5b,H5c), C11(H11a,H11b,H11c),
 C4(H4a,H4b,H4c), C3(H3a,H3b,H3c), C19(H19a,H19b,H19c)
;
_olex2_submission_special_instructions 'No special instructions were received'