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_1576230
_publ_section_title
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 Chelation-assisted multiple and relay C--H functionalization of
 unactivated aliphatic E-alkenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC07408H
_journal_year                    2025
_chemical_formula_moiety         'C31 H38 N3 O6'
_chemical_formula_sum            'C31 H38 N3 O6'
_chemical_formula_weight         548.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-26
_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                90
_cell_angle_beta                 96.932(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6835(3)
_cell_length_b                   21.2737(12)
_cell_length_c                   12.2589(7)
_cell_measurement_reflns_used    7163
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.470
_cell_measurement_theta_min      3.640
_cell_volume                     1471.38(14)
_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 0.999
_diffrn_measured_fraction_theta_max 0.985
_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  0.0797
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25416
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.783
_diffrn_reflns_theta_min         3.159
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    0.446
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1306 before and 0.0747 after correction.
The Ratio of minimum to maximum transmission is 0.7762.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       needle
_exptl_crystal_F_000             586
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1753 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         6591
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0617
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+0.2402P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1357
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                4725
_reflns_number_total             6591
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc07408h3.cif
_cod_data_source_block           240424_w6_0m
_cod_database_code               1576230
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O6-C22 \\sim O6-C22A
 with sigma of 0.02
 C21-C22 \\sim C21-C22A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O5 \\sim C21 \\sim C22A \\sim C22: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 2A
4. Others
 Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22C)=Sof(H22D)=1-FVAR(1)
 Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B), C6(H6A,H6B), C24(H24A,H24B), C25(H25A,H25B),
 C21(H21A,H21B), C21(H21C,H21D), C22(H22A,H22B), C22A(H22C,H22D)
5.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C1(H1), C2(H2), C3(H3), C27(H27), C18(H18), C10(H10), C31(H31),
 C29(H29), C11(H11), C30(H30), C28(H28)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C23(H23A,H23B,
 H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'