Highly regioselective and diastereodivergent aminomethylative annulation of dienyl alcohols enabled by a hydrogen-bonding assisting effect
Huang, Yao; Zou, Suchen; Yu, Bangkui; Yan, Xuyang; Liu, Song; Huang, Hanmin; Chemical Science 13 (2022) 2317–2323; doi:10.1039/D1SC06479G

data_1566268
_publ_section_title
;
 Highly regioselective and diastereodivergent aminomethylative annulation
 of dienyl alcohols enabled by a hydrogen-bonding assisting effect
;
_journal_issue                   8
_journal_name_full               'Chemical Science'
_journal_page_first              2317
_journal_page_last               2323
_journal_paper_doi               10.1039/D1SC06479G
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C25 H24 N2 O5 S'
_chemical_formula_sum            'C25 H24 N2 O5 S'
_chemical_formula_weight         464.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-25 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.5530(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.60983(19)
_cell_length_b                   31.1413(5)
_cell_length_c                   10.11618(15)
_cell_measurement_reflns_used    6630
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.7990
_cell_measurement_theta_min      4.1430
_cell_volume                     4600.86(12)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18304
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.048
_diffrn_reflns_theta_min         4.150
_exptl_absorpt_coefficient_mu    1.582
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         8507
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0591
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2117
_refine_ls_wR_factor_ref         0.2480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6188
_reflns_number_total             8507
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06479g2.cif
_cod_data_source_block           hy-x20927-1
_cod_depositor_comments
'Adding full bibliography for 1566266--1566268.cif.'
_cod_original_cell_volume        4600.85(12)
_cod_database_code               1566268
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.797
_shelx_estimated_absorpt_t_min   0.743
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C24-C25
 1.5 with sigma of 0.01
3. Rigid bond restraints
 C11, C12
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.005
4.a Ternary CH refined with riding coordinates:
 C33(H33), C41(H41), C15(H15), C23(H23)
4.b Secondary CH2 refined with riding coordinates:
 C32(H32a,H32b), C44(H44a,H44b), C14(H14a,H14b), C7(H7a,H7b), C40(H40a,H40b),
 C22(H22a,H22b)
4.c Aromatic/amide H refined with riding coordinates:
 C35(H35), C50(H50), C36(H36), C9(H9), C3(H3), C28(H28), C5(H5), C13(H13),
 C38(H38), C2(H2), C6(H6), C46(H46), C37(H37), C42(H42), C30(H30), C31(H31),
 C49(H49), C47(H47), C27(H27), C10(H10), C11(H11), C12(H12), C17(H17), C48(H48),
  C19(H19), C20(H20), C24(H24), C18(H18)
4.d X=CH2 refined with riding coordinates:
 C43(H43a,H43b), C25(H25a,H25b)
;
_shelx_res_checksum              91046
_shelx_hkl_checksum              13548
_olex2_submission_special_instructions 'No special instructions were received'