Asymmetric Synthesis of Fluorinated Amino Macrolactones through Ring-Closing Metathesis
Santos Fustero; Begoña Fernández; Juan F. Sanz-Cervera; Natalia Mateu; Silvia Mosulén; Rodrigo J. Carbajo; Antonio Pineda-Lucena; Carmen Ramírez de Arellano; Journal of Organic Chemistry 72 (2007) 8716–8723; doi:10.1021/jo701484w

data_4023024
_publ_section_title
;
 Asymmetric Synthesis of Fluorinated Amino Macrolactones
 through Ring-Closing Metathesis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8716
_journal_page_last               8723
_journal_paper_doi               10.1021/jo701484w
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration rm
_chemical_formula_sum            'C17 H17 F4 N O4'
_chemical_formula_weight         375.32
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2691(11)
_cell_length_b                   14.262(3)
_cell_length_c                   21.962(4)
_cell_measurement_reflns_used    6214
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1650.3(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 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.1688
_diffrn_reflns_av_sigmaI/netI    0.0880
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9969
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         5.11
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.624
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.212
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.495
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         1692
_refine_ls_number_restraints     362
_refine_ls_restrained_S_all      2.251
_refine_ls_R_factor_all          0.2087
_refine_ls_R_factor_gt           0.1818
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4354
_refine_ls_wR_factor_ref         0.4479
_reflns_number_gt                1249
_reflns_number_total             1692
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701484w1.cif
_cod_data_source_block           sfbf102
_cod_database_code               4023024