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_1566267
_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 H22 N3 O7 S'
_chemical_formula_sum            'C25 H21 N3 O7 S'
_chemical_formula_weight         507.51
_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             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                91.614(3)
_cell_angle_beta                 94.807(2)
_cell_angle_gamma                100.145(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2994(2)
_cell_length_b                   8.0887(3)
_cell_length_c                   21.2887(8)
_cell_measurement_reflns_used    4567
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.6360
_cell_measurement_theta_min      5.5650
_cell_volume                     1231.76(7)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.958
_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  0.0146
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7263
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.870
_diffrn_reflns_theta_min         4.172
_exptl_absorpt_coefficient_mu    1.604
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4455
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0983P)^2^+0.5151P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1702
_refine_ls_wR_factor_ref         0.1764
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3980
_reflns_number_total             4455
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06479g2.cif
_cod_data_source_block           hy-x2020921
_cod_depositor_comments
'Adding full bibliography for 1566266--1566268.cif.'
_cod_database_code               1566267
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.795
_shelx_estimated_absorpt_t_min   0.690
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C10-C11
 1.5 with sigma of 0.01
3. Rigid bond restraints
 C10, C11
 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:
 C8(H8), C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C13(H13a,H13b)
4.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C22(H22), C21(H21), C6(H6), C4(H4), C5(H5), C1(H1), C15(H15),
 C19(H19), C3(H3), C10(H10), C17(H17), C16(H16), C18(H18)
4.d X=CH2 refined with riding coordinates:
 C11(H11a,H11b)
;
_shelx_res_checksum              48926
_shelx_hkl_checksum              85673
_olex2_submission_special_instructions 'No special instructions were received'