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_1566266
_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_absolute_configuration ad
_chemical_formula_moiety         'C25 H23 N3 O7 S'
_chemical_formula_sum            'C25 H23 N3 O7 S'
_chemical_formula_weight         509.52
_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             2021-04-09
_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                 104.4290(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.58320(10)
_cell_length_b                   15.88330(10)
_cell_length_c                   10.58560(10)
_cell_measurement_reflns_used    6832
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0240
_cell_measurement_theta_min      5.1420
_cell_volume                     1234.78(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -41.00   9.00   1.00    1.00    --  -40.80  38.00 120.00   50
  2  \w   -129.00  40.00   1.00    1.00    --  -40.80   0.00  60.00  169
  3  \w     23.00  65.00   1.00    1.00    --   40.80 -99.00  30.00   42
  4  \w     82.00 122.00   1.00    1.00    --   40.80 178.00 -60.00   40
  5  \w     44.00 113.00   1.00    2.00    --   99.68-125.00-120.00   69
  6  \w     40.00 102.00   1.00    2.00    --   99.68 -94.00  90.00   62
  7  \w    104.00 174.00   1.00    2.00    --   99.68  77.00 -60.00   70
  8  \w    103.00 160.00   1.00    2.00    --   99.68  77.00-150.00   57
  9  \w     25.00 128.00   1.00    2.00    --   99.68 -30.00 -90.00  103
 10  \w    109.00 142.00   1.00    2.00    --   99.68  77.00 -90.00   33
 11  \w     24.00 122.00   1.00    2.00    --   99.68 -77.00-120.00   98
 12  \w    109.00 156.00   1.00    2.00    --   99.68  77.00   0.00   47
 13  \w    114.00 167.00   1.00    2.00    --   99.68  77.00  60.00   53
 14  \w    121.00 158.00   1.00    2.00    --   99.68 125.00 -90.00   37
 15  \w    107.00 175.00   1.00    2.00    --   99.68  77.00-120.00   68
 16  \w     48.00  89.00   1.00    2.00    --   99.68 -94.00  30.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0042480000
_diffrn_orient_matrix_UB_12      0.0596682000
_diffrn_orient_matrix_UB_13      -0.1154354000
_diffrn_orient_matrix_UB_21      0.0399604000
_diffrn_orient_matrix_UB_22      0.0752852000
_diffrn_orient_matrix_UB_23      0.0946247000
_diffrn_orient_matrix_UB_31      0.2059041000
_diffrn_orient_matrix_UB_32      -0.0133542000
_diffrn_orient_matrix_UB_33      0.0174252000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8204
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.944
_diffrn_reflns_theta_min         4.313
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 1947 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.822
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4459
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.822
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0379
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0976
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                4373
_reflns_number_total             4459
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06479g2.cif
_cod_data_source_block           hy-cis
_cod_depositor_comments
'Adding full bibliography for 1566266--1566268.cif.'
_cod_database_code               1566266
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         c20h20n2o2s1
_shelx_estimated_absorpt_t_max   0.856
_shelx_estimated_absorpt_t_min   0.645
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C25(H25), C24(H24), C7(H7), C3(H3), C11(H11), C14(H14), C6(H6),
 C5(H5), C12(H12), C18(H18), C4(H4), C13(H13)
2.d X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
;
_shelx_res_checksum              41817
_shelx_hkl_checksum              37841
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.305
_oxdiff_exptl_absorpt_empirical_full_min 0.772