Eco-friendly α,β-C(sp<sup>3</sup>)-H difunctionalization of tertiary amines <i>via</i> sequential [1,5]-hydride transfer and hetero-Diels-Alder cyclization.
Zhang, Yi; Yan, Huihui; Zhao, Peng; Chen, Rener; Fang, Weiwei; Wang, Lei; Ma, Yongmin; Chemical communications (Cambridge, England) 60 (2024) 10712–10715; doi:10.1039/d4cc02858a

data_7133630
_publ_section_title
;
 Eco-friendly &#x3b1;,&#x3b2;-C(sp<sup>3</sup>)-H difunctionalization of
 tertiary amines <i>via</i> sequential [1,5]-hydride transfer and
 hetero-Diels-Alder cyclization.
;
_journal_issue                   77
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10712
_journal_page_last               10715
_journal_paper_doi               10.1039/d4cc02858a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C38 H44 N3 O'
_chemical_formula_sum            'C30 H40 N2 O2'
_chemical_formula_weight         460.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-11
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_audit_update_record
;
2023-11-09 deposited with the CCDC.	2024-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.013(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2032(10)
_cell_length_b                   16.3569(13)
_cell_length_c                   14.4981(11)
_cell_measurement_reflns_used    5930
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.735
_cell_measurement_theta_min      2.385
_cell_volume                     3126.7(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            59745
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.371
_diffrn_reflns_theta_min         1.878
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0704 before and 0.0647 after correction.
The Ratio of minimum to maximum transmission is 0.9012.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.979
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         7800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0674
_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^)+(0.1162P)^2^+0.7635P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1880
_refine_ls_wR_factor_ref         0.2326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4336
_reflns_number_total             7800
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02858a2.cif
_cod_data_source_block           mo230510a
_cod_depositor_comments
'Adding full bibliography for 7133630--7133631.cif.'
_cod_database_code               7133630
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.991
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N3(H3), C4(H4), C5(H5), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C34(H34A,H34B), C35(H35A,H35B),
  C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C18(H18), C19(H19),
 C20(H20), C21(H21), C29(H29), C30(H30), C31(H31), C32(H32)
;
_shelx_res_checksum              80477
_shelx_hkl_checksum              44830
_olex2_submission_special_instructions 'No special instructions were received'