Control of the diastereoselectivity at C(20) in the formation of C(21)-fluorinated thevinols.
Sandulenko, Irina V.; Kovaleva, Ekaterina S.; Zelentsova, Maria V.; Ambartsumyan, Asmik A.; Gorlov, Sergey N.; Danshina, Anastasia A.; Aysin, Rinat R.; Moiseev, Sergey K.; Organic & biomolecular chemistry 21 (2023) 1440–1449; doi:10.1039/d2ob02144g

data_7159086
_publ_section_title
;
 Control of the diastereoselectivity at C(20) in the formation of
 C(21)-fluorinated thevinols.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1440
_journal_page_last               1449
_journal_paper_doi               10.1039/d2ob02144g
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C25 H30 F3 N O4'
_chemical_formula_sum            'C25 H30 F3 N O4'
_chemical_formula_weight         465.50
_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   mixed
_audit_creation_date             2022-11-03
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-03 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.4980(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5849(3)
_cell_length_b                   10.6443(3)
_cell_length_c                   15.6105(4)
_cell_measurement_reflns_used    5166
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.96
_cell_measurement_theta_min      2.20
_cell_volume                     2219.52(10)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_unetI/netI     0.1037
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33721
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.575
_diffrn_reflns_theta_min         1.830
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0921 before and 0.0606 after correction.
The Ratio of minimum to maximum transmission is 0.9115.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 3040 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     611
_refine_ls_number_reflns         13076
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0580
_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^)+(0.0372P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1151
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                9010
_reflns_number_total             13076
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02144g2.cif
_cod_data_source_block           gor008
_cod_depositor_comments
'Adding full bibliography for 7159086--7159090.cif.'
_cod_database_code               7159086
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.978
_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:
 C5(H5), C7(H7), C9(H9), C5A(H5A), C7A(H7A), C9A(H9A)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B), C22(H22A,H22B),
 C8A(H8AA,H8AB), C10A(H10C,H10D), C15A(H15C,H15D), C16A(H16C,H16D), C22A(H22C,
 H22D)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C18(H18), C19(H19), C1A(H1A), C2A(H2A), C18A(H18A), C19A(H19A)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C17A(H17D,H17E,H17F), C23A(H23D,H23E,H23F), C24A(H24D,H24E,H24F),
 C25A(H25D,H25E,H25F)
;
_olex2_submission_special_instructions 'No special instructions were received'