Influence of the Trans/Cis Conformer Ratio on the Stereoselectivity of Peptidic Catalysts.
Schnitzer, Tobias; Wennemers, Helma; Journal of the American Chemical Society 139 (2017) 15356–15362; doi:10.1021/jacs.7b06194

data_4131515
_publ_section_title
;
 Influence of the Trans/Cis Conformer Ratio on the Stereoselectivity of
 Peptidic Catalysts.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15356
_journal_page_last               15362
_journal_paper_doi               10.1021/jacs.7b06194
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C2 F3 O2, C15 H25 N4 O5'
_chemical_formula_sum            'C17 H25 F3 N4 O7'
_chemical_formula_weight         454.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-03
_audit_creation_method
;
Olex2 1.2
(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            4
_cell_length_a                   9.7372(11)
_cell_length_b                   14.0027(18)
_cell_length_c                   14.9230(18)
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.50
_cell_volume                     2034.7(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'double mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            56103
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_min         2.498
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms high brilliance'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.7354
_exptl_absorpt_correction_T_min  0.6935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1297 before and 0.0531 after correction.
The Ratio of minimum to maximum transmission is 0.9430.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1789 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4716
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0293
_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^)+(0.0306P)^2^+0.5418P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0704
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4323
_reflns_number_total             4716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b06194_si_002.cif
_cod_data_source_block           w010316_1_1_0m
_cod_database_code               4131515
_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 O(H) groups
2. Restrained distances
 N12-H12A = N12-H12B
 0.91 with sigma of 0.02
 N4-H4A = N4-H4B
 0.91 with sigma of 0.02
 N2-H2
 0.91 with sigma of 0.02
 O3-H3
 0.91 with sigma of 0.02
 C14A-C10 \\sim C14-C10
 with sigma of 0.02
 C14A-C13 \\sim C14-C13
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C2, C0AA, F2, F1, F3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H10C)=Sof(H10D)=Sof(H13C)=Sof(H13D)=Sof(C14A)=Sof(H14C)=Sof(H14D)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4C,H4D), C10(H10A,H10B), C10(H10C,H10D), C13(H13A,H13B),
 C13(H13C,H13D), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
  C14A(H14C,H14D)
;
_shelx_res_checksum              46010
_shelx_hkl_checksum              70484
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-03-02
_olex2_date_sample_submission    2016-03-02
_olex2_submission_original_sample_id w010316_1_1
_olex2_submission_special_instructions 'No special instructions were received'