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_4037443
_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         'C24 H30 F3 N O6'
_chemical_formula_sum            'C24 H30 F3 N O6'
_chemical_formula_weight         485.49
_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     direct
_audit_creation_date             2016-06-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.8948(9)
_cell_length_b                   9.9946(5)
_cell_length_c                   23.9226(11)
_cell_measurement_reflns_used    9000
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.55
_cell_measurement_theta_min      2.43
_cell_volume                     4756.8(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_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  0.0609
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            79617
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        28.498
_diffrn_reflns_theta_max         28.498
_diffrn_reflns_theta_min         2.047
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1725 before and 0.0632 after correction.
The Ratio of minimum to maximum transmission is 0.9265.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.643
_exptl_crystal_size_mid          0.413
_exptl_crystal_size_min          0.213
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         6027
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0430P)^2^+2.7050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4698
_reflns_number_total             6027
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02346_si_001.cif
_cod_data_source_block           12g
_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               4037443
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.932
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F1-C6 \\sim F1-C6B \\sim F3B-C6B \\sim F3-C6 \\sim F2B-C6B \\sim F2-C6
 with sigma of 0.02
 C6B-C1 \\sim C6-C1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C6) = Uanis(C6B)
4. Others
 Uiso(H7A)=Uiso(H7B)=Uiso(H7C)=FVAR(1)
 Uiso(H18A)=Uiso(H18B)=Uiso(H18C)=FVAR(2)
 Uiso(H19A)=Uiso(H19B)=Uiso(H19C)=FVAR(3)
 Uiso(H20A)=Uiso(H20B)=Uiso(H20C)=FVAR(4)
 Uiso(H22A)=Uiso(H22B)=Uiso(H22C)=FVAR(5)
 Uiso(H23A)=Uiso(H23B)=Uiso(H23C)=FVAR(6)
 Uiso(H24A)=Uiso(H24B)=Uiso(H24C)=FVAR(7)
 Fixed Sof: F2(0.9) F3(0.9) C6(0.9) F2B(0.1) F3B(0.1) C6B(0.1)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C17(H17A,H17B)
5.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C16(H16)
5.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'