Chelation-assisted multiple and relay C–H functionalization of unactivated aliphatic E-alkenes
Wang, Yini; Li, Xiaoli; Peng, Chengxing; Chen, Yu; Lu, Xi; Zhu, Yuhang; Yu, Peiyuan; Zhong, Guofu; Zhang, Jian; Chemical Science  (2025) –; doi:10.1039/D5SC07408H

data_1576231
_publ_section_title
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 Chelation-assisted multiple and relay C--H functionalization of
 unactivated aliphatic E-alkenes
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_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC07408H
_journal_year                    2025
_chemical_formula_moiety         'C40 H33 F4 N3 O'
_chemical_formula_sum            'C40 H33 F4 N3 O'
_chemical_formula_weight         647.69
_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             2024-06-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-01-25 deposited with the CCDC.	2025-10-24 downloaded from the CCDC.
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_cell_angle_alpha                93.445(4)
_cell_angle_beta                 90.785(4)
_cell_angle_gamma                103.964(4)
_cell_formula_units_Z            4
_cell_length_a                   10.4082(9)
_cell_length_b                   12.4962(11)
_cell_length_c                   27.205(3)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.041
_cell_measurement_theta_min      2.833
_cell_volume                     3426.1(6)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_av_unetI/netI     0.0986
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            49185
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.143
_diffrn_reflns_theta_min         1.416
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.6733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0943 before and 0.0659 after correction.
The Ratio of minimum to maximum transmission is 0.8970.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       plate
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.061
_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     867
_refine_ls_number_reflns         12483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0656
_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^)+(0.0960P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1776
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7398
_reflns_number_total             12483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc07408h3.cif
_cod_data_source_block           240612_tp_f
_cod_original_cell_volume        3426.2(5)
_cod_database_code               1576231
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.963
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00T(H00A,H00B), C56(H56A,H56B), C57(H57A,H57B), C74(H74A,H74B), C16(H16A,
 H16B), C17(H17A,H17B), C34(H34A,H34B), C35(H35A,H35B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4A), C41(H41), C42(H42), C44(H44), C45(H45), C47(H47), C50(H50), C51(H51),
  C53(H53), C54(H54), C61(H61), C63(H63), C64(H64), C66(H66), C67(H67),
 C69(H69), C70(H70), C72(H72), C73(H73), C77(H77), C78(H78), C79(H79), N1(H1),
 C1(H1A), C2(H2), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C13(H13),
 C14(H14), C21(H21), C23(H23), C24(H24), C26(H26), C27(H27), C29(H29), C30(H30),
  C32(H32), C33(H33), C38(H38), C39(H39), C40(H40)
2.c Idealised Me refined as rotating group:
 C58(H58A,H58B,H58C), C18(H18A,H18B,H18C)
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_olex2_submission_special_instructions 'No special instructions were received'