B(MIDA)-directed site-selective intermolecular halofluoroalkylation of alkenes: synthesis of diversely functionalized building blocks.
Wu, Hengbo; Luo, Ruitong; Peng, Jingjing; Han, Zijian; Zhang, Renjie; Xu, Zhijian; Zhu, Weiliang; Liu, Hong; Li, Chunpu; Chemical science 16 (2025) 2710–2717; doi:10.1039/d4sc07900k

data_1573677
_publ_section_title
;
 B(MIDA)-directed site-selective intermolecular halofluoroalkylation of
 alkenes: synthesis of diversely functionalized building blocks.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              2710
_journal_page_last               2717
_journal_paper_doi               10.1039/d4sc07900k
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C11 H15 B F2 I N O6'
_chemical_formula_sum            'C11 H15 B F2 I N O6'
_chemical_formula_weight         432.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-17 deposited with the CCDC.	2024-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 126.597(7)
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   51.208(5)
_cell_length_b                   7.1184(7)
_cell_length_c                   31.560(4)
_cell_measurement_reflns_used    8171
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.061
_cell_measurement_theta_min      2.338
_cell_volume                     9236.1(19)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       60
_diffrn_reflns_limit_h_min       -60
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            29505
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.084
_diffrn_reflns_theta_max         25.084
_diffrn_reflns_theta_min         0.991
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.128
_exptl_absorpt_correction_T_max  0.0329
_exptl_absorpt_correction_T_min  0.0146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1847 before and 0.0562 after correction. The Ratio of minimum to maximum transmission is 0.4438. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.868
_exptl_crystal_description       needle
_exptl_crystal_F_000             5088
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.140
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         7974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0272P)^2^+36.3093P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5860
_reflns_number_total             7974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07900k2.cif
_cod_data_source_block           20211478
_cod_depositor_comments          'Adding full bibliography for 1573677.cif.'
_cod_original_cell_volume        9236.0(18)
_cod_database_code               1573677
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.416
_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:
 C17(H17), C6(H6), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C16(H16A,H16B), C18(H18A,H18B), C23(H23A,H23B), C12(H12A,
 H12B), C7(H7A,H7B), C4(H4A,H4B), C26(H26A,H26B), C33(H33A,H33B), C2(H2A,H2B),
 C21(H21A,H21B), C10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C14(H14A,H14B,H14C), C3(H3A,H3B,H3C), C32(H32A,H32B,
 H32C), C11(H11A,H11B,H11C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'