Synthesis of Gly-ψ[(Z)CF═CH]-Phe, a Fluoroalkene Dipeptide Isostere, and Its Incorporation into a Leu-enkephalin Peptidomimetic.
Nadon, Jean-François; Rochon, Kristina; Grastilleur, Sébastien; Langlois, Guillaume; Dao, Thi Thanh Hà; Blais, Véronique; Guérin, Brigitte; Gendron, Louis; Dory, Yves L.; ACS chemical neuroscience 8 (2017) 40–49; doi:10.1021/acschemneuro.6b00163

data_4514018
_publ_section_title
;
 Synthesis of Gly-\y[(Z)CF&#x2550;CH]-Phe, a Fluoroalkene Dipeptide
 Isostere, and Its Incorporation into a Leu-enkephalin Peptidomimetic.
;
_journal_issue                   1
_journal_name_full               'ACS chemical neuroscience'
_journal_page_first              40
_journal_page_last               49
_journal_paper_doi               10.1021/acschemneuro.6b00163
_journal_volume                  8
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H37 F N2 O5 S'
_chemical_formula_weight         520.65
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2013-05-08T10:11:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2408(14)
_cell_length_b                   12.5092(16)
_cell_length_c                   23.734(3)
_cell_measurement_temperature    173(2)
_cell_volume                     2743.5(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.974
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            44719
_diffrn_reflns_theta_full        70
_diffrn_reflns_theta_max         71.6
_diffrn_reflns_theta_min         3.72
_exptl_absorpt_coefficient_mu    1.427
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.050(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0284P)^2^+1.3870P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.098
_reflns_number_gt                4762
_reflns_number_total             5165
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            cn6b00163_si_002.cif
_cod_data_source_block           cu_dory_jfn_03_143_0m
_cod_database_code               4514018