Total synthesis of (±)-3-demethoxyerythratidinone <i>via</i> Tf<sub>2</sub>O-promoted cascade reaction of enaminone.
Lou, Mingliang; Liu, Xiaolei; Han, Shoule; Bai, Songlin; Qi, Xiangbing; Chemical communications (Cambridge, England) 60 (2024) 3842–3845; doi:10.1039/d3cc06270h

data_7132832
_publ_section_title
;
 Total synthesis of (&#xb1;)-3-demethoxyerythratidinone <i>via</i>
 Tf<sub>2</sub>O-promoted cascade reaction of enaminone.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3842
_journal_page_last               3845
_journal_paper_doi               10.1039/d3cc06270h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C19 H17 F3 N2 O4 S'
_chemical_formula_sum            'C19 H17 F3 N2 O4 S'
_chemical_formula_weight         426.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2jdzjg
_audit_creation_date             2024-02-21
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-29 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   19.2019(4)
_cell_length_b                   13.9245(3)
_cell_length_c                   28.2926(5)
_cell_measurement_reflns_used    9829
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      67.929
_cell_measurement_theta_min      3.124
_cell_volume                     7564.8(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            162221
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.464
_diffrn_reflns_theta_min         3.124
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.061
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0761 before and 0.0575 after correction.
The Ratio of minimum to maximum transmission is 0.8948.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       block
_exptl_crystal_F_000             3520
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         6950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0505P)^2^+4.4956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1046
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6154
_reflns_number_total             6950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc06270h2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7132832--7132833.cif.'
_cod_database_code               7132832
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.820
_shelx_estimated_absorpt_t_min   0.790
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C33(H33)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B), C31(H31A,
 H31B), C32(H32A,H32B), C34(H34A,H34B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C20(H20), C21(H21), C22(H22),
 C25(H25), C37(H37)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              76493
_shelx_hkl_checksum              65036
_olex2_submission_special_instructions 'No special instructions were received'