Diastereoselective Trifluoroacetylation of Highly Substituted Pyrrolidines by a Dakin-West Process.
Baumann, Marcus; Baxendale, Ian R.; The Journal of organic chemistry 81 (2016) 11898–11908; doi:10.1021/acs.joc.6b02346

data_4037444
_publ_section_title
;
 Diastereoselective Trifluoroacetylation of Highly Substituted
 Pyrrolidines by a Dakin-West Process.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11898
_journal_page_last               11908
_journal_paper_doi               10.1021/acs.joc.6b02346
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C25 H28 F7 N O5'
_chemical_formula_sum            'C25 H28 F7 N O5'
_chemical_formula_weight         555.48
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-22
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_cell_angle_alpha                101.028(3)
_cell_angle_beta                 92.592(3)
_cell_angle_gamma                111.947(3)
_cell_formula_units_Z            4
_cell_length_a                   9.3392(6)
_cell_length_b                   12.0373(8)
_cell_length_c                   25.2796(17)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.438
_cell_measurement_theta_min      2.203
_cell_volume                     2565.9(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2016)'
_computing_data_collection       'APEX3 v.2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 multi-CPU (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  D8V_Mo
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            47813
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.569
_diffrn_reflns_theta_min         2.203
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1087 before and 0.0632 after correction.
The Ratio of minimum to maximum transmission is 0.8896.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     733
_refine_ls_number_reflns         11788
_refine_ls_number_restraints     558
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0855
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+10.4260P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2158
_refine_ls_wR_factor_ref         0.2254
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9349
_reflns_number_total             11788
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02346_si_001.cif
_cod_data_source_block           17h
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4037444
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.973
_exptl_twin_twinlaw_details      '-1 0 0 0 -1 0 0.734 1.016 1'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.846(2) 0.154(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Restrained distances
 F6A-C21A \\sim F5B-C21B \\sim F5A-C21A \\sim F4B-C21B \\sim F4A-C21A \\sim
F6B-C21B
 with sigma of 0.02
 F5A-C21A \\sim F4A-C21A \\sim F6A-C21A \\sim F4B-C21B \\sim F6B-C21B \\sim
F5B-C21B
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uiso(C21A) = Uiso(C21B)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Uiso(H6A)=Uiso(H6B)=Uiso(H6C)=FVAR(1)
 Uiso(H17A)=Uiso(H17B)=Uiso(H17C)=FVAR(2)
 Uiso(H18A)=Uiso(H18B)=Uiso(H18C)=FVAR(3)
 Uiso(H19A)=Uiso(H19B)=Uiso(H19C)=FVAR(4)
 Uiso(H23A)=Uiso(H23B)=Uiso(H23C)=FVAR(5)
 Uiso(H24A)=Uiso(H24B)=Uiso(H24C)=FVAR(6)
 Uiso(H25A)=Uiso(H25B)=Uiso(H25C)=FVAR(7)
 Uiso(H6'A)=Uiso(H6'B)=Uiso(H6'C)=FVAR(8)
 Uiso(H17D)=Uiso(H17E)=Uiso(H17F)=FVAR(9)
 Uiso(H18D)=Uiso(H18E)=Uiso(H18F)=FVAR(10)
 Uiso(H19D)=Uiso(H19E)=Uiso(H19F)=FVAR(11)
 Uiso(H23D)=Uiso(H23E)=Uiso(H23F)=FVAR(12)
 Uiso(H24D)=Uiso(H24E)=Uiso(H24F)=FVAR(13)
 Uiso(H25D)=Uiso(H25E)=Uiso(H25F)=FVAR(14)
 Fixed Sof: F4A(0.67) F5A(0.67) F6A(0.67) F4B(0.33) F5B(0.33) F6B(0.33)
 C21A(0.67) C21B(0.33) F7A'(0.85) F7B'(0.15)
7.a Ternary CH refined with riding coordinates:
 C8(H8), C8'(H8')
7.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C4'(H4'A,H4'B)
7.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C13(H13), C14(H14), C10'(H10'), C12'(H12'), C13'(H13'),
 C14'(H14')
7.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C6'(H6'A,
 H6'B,H6'C), C17'(H17D,H17E,H17F), C18'(H18D,H18E,H18F), C19'(H19D,H19E,H19F),
 C23'(H23D,H23E,H23F), C24'(H24D,H24E,H24F), C25'(H25D,H25E,H25F)
;
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'