New Fluorinated Peptidomimetics through Tandem Aza-Michael Addition to α-Trifluoromethyl Acrylamide Acceptors: Synthesis and Conformational Study in Solid State and Solution
Santos Fustero; Gema Chiva; Julio Piera; Juan F. Sanz-Cervera; Alessandro Volonterio; Matteo Zanda; Carmen Ramírez de Arellano; Journal of Organic Chemistry 74 (2009) 3122–3132; doi:10.1021/jo9001867

data_4024479
_publ_contact_author_address
;Departamento de Qu\'imica Org\'anica
Universidad de Valencia
46100 Valencia
Spain
;
_publ_contact_author_email       Carmen.ramirezdearellano@uv.es
_publ_contact_author_fax         +34963544939
_publ_contact_author_name        'Carmen Ram\'irez de Arellano'
_publ_contact_author_phone       +34963543046
_publ_section_title
;
New Fluorinated Peptidomimetics through Tandem Aza-Michael Addition to
\a-Trifluoromethyl Acrylamide Acceptors: Synthesis and Conformational Study
in Solid State and Solution
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3122
_journal_page_last               3132
_journal_paper_doi               10.1021/jo9001867
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_sum            'C16 H28 F3 N3 O4'
_chemical_formula_weight         383.41
_chemical_name_common            gt363c
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.64(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.503(2)
_cell_length_b                   9.1652(18)
_cell_length_c                   10.804(2)
_cell_measurement_reflns_used    4307
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1038.9(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'SHELXTL v6.14 (Bruker, 2000-2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7646
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         5.18
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.8(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2250
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0299P)^2^+0.0933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0781
_reflns_number_gt                1625
_reflns_number_total             2250
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9001867_si_002_3.cif
_cod_data_source_block           gt363c_compound_8c
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4024479