Fluorine containing amino acids: synthesis and peptide coupling of amino acids containing the all-cis tetrafluorocyclohexyl motif.
Ayoup, Mohammed Salah; Cordes, David B.; Slawin, Alexandra M. Z.; O'Hagan, David; Organic & biomolecular chemistry 13 (2015) 5621–5624; doi:10.1039/c5ob00650c

data_7154424
_publ_section_title
;
 Fluorine containing amino acids: synthesis and peptide coupling of amino
 acids containing the all-cis tetrafluorocyclohexyl motif.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5621
_journal_page_last               5624
_journal_paper_doi               10.1039/c5ob00650c
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H18 F4 N O2, Cl'
_chemical_formula_sum            'C15 H18 Cl F4 N O2'
_chemical_formula_weight         355.76
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-31
_audit_creation_method           'by CrystalStructure 4.1'
_audit_update_record
;
2015-03-31 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.301(6)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   5.3827(19)
_cell_length_b                   7.108(2)
_cell_length_c                   20.990(7)
_cell_measurement_reflns_used    844
_cell_measurement_temperature    173
_cell_measurement_theta_max      47.30
_cell_measurement_theta_min      19.10
_cell_volume                     796.6(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1436
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7844
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.293
_diffrn_reflns_theta_min         2.122
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.606
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             368.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1,4-dioxane/water'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.59
_refine_diff_density_min         -0.33
_refine_ls_abs_structure_details
;
 Flack x determined using 359 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_coef       0.038(9)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2667
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0966
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1611P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2465
_refine_ls_wR_factor_ref         0.2711
_reflns_number_gt                1704
_reflns_number_total             2667
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c5ob00650c2.cif
_cod_data_source_block           11
_cod_depositor_comments          'Adding full bibliography for 7154424.cif.'
_cod_database_code               7154424
_shelx_res_checksum              96819