Photoinduced boryl-oximation of alkenes <i>via</i> NHC-boryl radical generation.
Huang, Qiang; Li, Na; Zhang, Panke; Li, Hongji; Chemical science 16 (2025) 19263–19270; doi:10.1039/d5sc03708e

data_1575698
_publ_section_title
;
 Photoinduced boryl-oximation of alkenes <i>via</i> NHC-boryl radical
 generation.
;
_journal_issue                   41
_journal_name_full               'Chemical science'
_journal_page_first              19263
_journal_page_last               19270
_journal_paper_doi               10.1039/d5sc03708e
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         '2(C13 H17 B Br N3 O)'
_chemical_formula_sum            'C26 H34 B2 Br2 N6 O2'
_chemical_formula_weight         644.03
_chemical_name_systematic        hq
_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     dual
_audit_creation_date             2024-12-05
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-05-04 deposited with the CCDC.	2025-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.119(8)
_cell_angle_beta                 90.084(10)
_cell_angle_gamma                94.565(9)
_cell_formula_units_Z            2
_cell_length_a                   6.1608(15)
_cell_length_b                   13.731(3)
_cell_length_c                   17.545(4)
_cell_measurement_reflns_used    1064
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.98
_cell_volume                     1479.5(6)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            61280
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.593
_diffrn_reflns_theta_min         2.761
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.774
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1182 before and 0.0529 after correction.
The Ratio of minimum to maximum transmission is 0.5223.
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    1.446
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         6789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0311P)^2^+1.1967P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0881
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5522
_reflns_number_total             6789
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03708e2.cif
_cod_data_source_block           20241023b_0m
_cod_depositor_comments          'Adding full bibliography for 1575698.cif.'
_cod_original_cell_volume        1479.4(6)
_cod_database_code               1575698
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.921
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H,H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00B), C00I(H00C,H00D), B2(H2A,H2B), B1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W)
2.c Idealised Me refined as rotating group:
 C00Z(H00E,H00F,H00G), C010(H01A,H01B,H01C), C011(H01G,H01H,H01I), C012(H01D,
 H01E,H01F)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003), O004(H004)
;
_shelx_res_checksum              96926
_olex2_submission_special_instructions 'No special instructions were received'