Synthesis of Tripeptide Derivatives with Three Stereogenic Centers and Chiral Recognition Probed by Tetraaza Macrocyclic Chiral Solvating Agents Derived from d-Phenylalanine and (1 S,2 S)-(+)-1,2-Diaminocyclohexane via <sup>1</sup>H NMR Spectroscopy.
Feng, Lei; Gao, Guangpeng; Zhao, Hongmei; Zheng, Li; Wang, Yu; Stavropoulos, Pericles; Ai, Lin; Zhang, Jiaxin; The Journal of organic chemistry 83 (2018) 13874–13887; doi:10.1021/acs.joc.8b02212

data_4034867
_publ_section_title
;
 Synthesis of Tripeptide Derivatives with Three Stereogenic Centers and
 Chiral Recognition Probed by Tetraaza Macrocyclic Chiral Solvating Agents
 Derived from d-Phenylalanine and (1 S,2 S)-(+)-1,2-Diaminocyclohexane via
 <sup>1</sup>H NMR Spectroscopy.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13874
_journal_page_last               13887
_journal_paper_doi               10.1021/acs.joc.8b02212
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C38 H40 Cl2 N4 O4'
_chemical_formula_weight         687.64
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 92.29(3)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   15.809(3)
_cell_length_b                   37.886(8)
_cell_length_c                   26.539(5)
_cell_measurement_reflns_used    158886
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      0.768
_cell_volume                     15883(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics
;
OLEX2: A complete structure solution, refinement and analysis program.
(Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; 
Puschmann, H., J. Appl. Cryst., 2009, 42, 339-341.)
;
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            158886
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         0.768
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_description       block
_exptl_crystal_F_000             5792
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.500
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 17414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     3078
_refine_ls_number_reflns         58965
_refine_ls_number_restraints     3829
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.1032
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1832P)^2^+9.6390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2902
_refine_ls_wR_factor_ref         0.3035
_reflns_Friedel_coverage         0.965
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                50256
_reflns_number_total             58965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02212_si_003.cif
_cod_data_source_block           1_sq
_cod_original_cell_volume        15883(6)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4034867
_shelxl_version_number           2014/6
_shelx_res_checksum              69529
_shelx_hkl_checksum              55389
_shelx_fab_checksum              5671