Synthesis of Optically Active Trifluoromethylated Indolizidine Derivatives via Stereoselective Radical Cyclization
Okano, Takashi; Fumoto, Masataka; Kusukawa, Takahiro; Fujita, Makoto; Organic Letters 4 (2002) 1571–; doi:10.1021/ol025792b

data_1507450
_publ_section_title
;
 Synthesis of Optically Active Trifluoromethylated Indolizidine
 Derivatives via Stereoselective Radical Cyclization
;
_journal_issue                   9
_journal_name_full               'Organic Letters'
_journal_page_first              1571
_journal_paper_doi               10.1021/ol025792b
_journal_volume                  4
_journal_year                    2002
_chemical_formula_sum            'C21 H27 F3 N2 O5'
_chemical_formula_weight         444.45
_chemical_name_systematic
; 
((1R,3Z)-4,4,4-trifluoro-3-{[(2R)-2-(mthoxymethyl)pyrrolidin-1-yl]imino}-1-
phenylbutyl)malonic acid dimethyl ester 
;
_space_group_IT_number           76
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_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                   12.229(7)
_cell_length_b                   12.229(7)
_cell_length_c                   15.675(9)
_cell_measurement_temperature    243(2)
_cell_volume                     2344(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0834
_diffrn_reflns_av_sigmaI/netI    0.0835
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8976
_diffrn_reflns_theta_full        19.77
_diffrn_reflns_theta_max         19.77
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         2117
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.892
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0546
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1543
_reflns_number_gt                1440
_reflns_number_total             2117
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol025792b_s1.cif
_cod_data_source_block           R-5a2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P4(1)
_cod_database_code               1507450