Construction of Diverse Polycyclic N-Heterocycles via Cascade Allylic Amination/Diels−Alder Reaction
Yang, Zhenkun; Xie, Hongling; Tang, Luning; Sun, Jianwei; Han, Zhengyu; Huang, Hai; Chemical Communications  (2022) –; doi:10.1039/D2CC05208C

data_7130959
_publ_section_title
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 Construction of Diverse Polycyclic N-Heterocycles via Cascade Allylic
 Amination/Diels&#x2212;Alder Reaction
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC05208C
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H27 N O5 S'
_chemical_formula_sum            'C24 H27 N O5 S'
_chemical_formula_weight         441.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-12
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_audit_update_record
;
2022-07-19 deposited with the CCDC.	2022-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.481(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3476(14)
_cell_length_b                   12.016(2)
_cell_length_c                   11.2069(19)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      60.511
_cell_measurement_theta_min      5.639
_cell_volume                     1116.9(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            39835
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.595
_diffrn_reflns_theta_min         4.638
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.031
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1402 before and 0.0948 after correction.
The Ratio of minimum to maximum transmission is 0.8125.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2191 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.062(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5028
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0679P)^2^+0.0512P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.980
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                4736
_reflns_number_total             5028
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05208c2.cif
_cod_data_source_block           a
_cod_database_code               7130959
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.904
_shelx_estimated_absorpt_t_min   0.886
_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, All O(H) groups
2. Restrained distances
 C24A-C23 \\sim C24-C23
 with sigma of 0.02
3. Others
 Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C14(H14), C15(H15), C21(H21)
4.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C16(H16A,H16B), C18(H18A,H18B), C23(H23A,H23B), C23(H23C,H23D)
4.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C12(H12), C11(H11), C10(H10), C6(H6), C9(H9), C19(H19), C3(H3A), C7(H7)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C24(H24A,H24B,H24C), C24A(H24D,H24E,H24F)
4.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              83450
_shelx_hkl_checksum              60709
_olex2_submission_special_instructions 'No special instructions were received'