#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/74/1507451.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1507451
loop_
_publ_author_name
'Okano, Takashi'
'Fumoto, Masataka'
'Kusukawa, Takahiro'
'Fujita, Makoto'
_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            'C12 H18 F3 N O'
_chemical_formula_weight         249.27
_chemical_name_systematic
; 
(7R,8aR)-7-phenyl-8a-(trifluoromethyl)hexahydroindolizin-5(1H)-one
;
_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                   5.9581(11)
_cell_length_b                   13.713(3)
_cell_length_c                   15.466(3)
_cell_measurement_temperature    243(2)
_cell_volume                     1263.6(4)
_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      243(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9332
_diffrn_reflns_theta_full        28.01
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   Empirical(SADABS)
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.1(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.597
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.597
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0421
_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/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1332
_reflns_number_gt                1307
_reflns_number_total             3048
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol025792b_s1.cif
_cod_data_source_block           10c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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      P2(1)2(1)2(1)
_cod_database_code               1507451
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F -0.1229(4) -0.91637(14) -0.75825(10) 0.0920(6) Uani 1 1 d .
F2 F 0.0290(4) -0.80293(12) -0.83238(10) 0.1051(7) Uani 1 1 d .
F3 F 0.2048(4) -0.93644(13) -0.81011(10) 0.1071(7) Uani 1 1 d .
N1 N 0.0095(4) -0.76784(14) -0.64762(14) 0.0572(5) Uani 1 1 d .
C1 C -0.1148(4) -0.7975(2) -0.58025(17) 0.0619(7) Uani 1 1 d .
C2 C -0.0890(4) -0.8983(2) -0.54600(18) 0.0666(7) Uani 1 1 d .
H2A H -0.2359 -0.9288 -0.5471 0.080 Uiso 1 1 calc R
H2B H -0.0451 -0.8931 -0.4858 0.080 Uiso 1 1 calc R
C3 C 0.0758(4) -0.96817(17) -0.59014(16) 0.0551(7) Uani 1 1 d .
H3A H -0.0041 -1.0024 -0.6365 0.066 Uiso 1 1 calc R
C4 C 0.2624(4) -0.90798(18) -0.63072(15) 0.0559(6) Uani 1 1 d .
H4A H 0.3606 -0.9510 -0.6631 0.067 Uiso 1 1 calc R
H4B H 0.3507 -0.8783 -0.5850 0.067 Uiso 1 1 calc R
C5 C 0.1775(4) -0.82828(16) -0.69071(16) 0.0533(6) Uani 1 1 d .
C6 C 0.3603(5) -0.75418(19) -0.7148(2) 0.0761(8) Uani 1 1 d .
H6A H 0.4751 -0.7517 -0.6704 0.091 Uiso 1 1 calc R
H6B H 0.4302 -0.7717 -0.7693 0.091 Uiso 1 1 calc R
C7 C 0.2410(7) -0.6560(2) -0.7225(2) 0.0938(10) Uani 1 1 d .
H7A H 0.3353 -0.6041 -0.7001 0.113 Uiso 1 1 calc R
H7B H 0.2058 -0.6419 -0.7824 0.113 Uiso 1 1 calc R
C8 C 0.0300(6) -0.66431(19) -0.6702(2) 0.0831(10) Uani 1 1 d .
H8A H 0.0400 -0.6246 -0.6184 0.100 Uiso 1 1 calc R
H8B H -0.0986 -0.6431 -0.7037 0.100 Uiso 1 1 calc R
C9 C 0.0737(6) -0.8703(2) -0.77277(18) 0.0717(8) Uani 1 1 d .
C10 C 0.1675(5) -1.0444(2) -0.52679(19) 0.0775(9) Uani 1 1 d .
H10A H 0.2469 -1.0096 -0.4806 0.093 Uiso 1 1 calc R
C11 C 0.3338(7) -1.1138(2) -0.5696(3) 0.1091(14) Uani 1 1 d .
H11A H 0.3874 -1.1599 -0.5277 0.164 Uiso 1 1 calc R
H11B H 0.4581 -1.0773 -0.5923 0.164 Uiso 1 1 calc R
H11C H 0.2606 -1.1480 -0.6158 0.164 Uiso 1 1 calc R
C12 C -0.0223(7) -1.1030(3) -0.4853(2) 0.1175(14) Uani 1 1 d .
H12A H 0.0397 -1.1493 -0.4453 0.176 Uiso 1 1 calc R
H12B H -0.1042 -1.1370 -0.5295 0.176 Uiso 1 1 calc R
H12C H -0.1215 -1.0596 -0.4551 0.176 Uiso 1 1 calc R
O1 O -0.2466(3) -0.73998(16) -0.54532(15) 0.0987(8) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C5 124.1(2)
C1 N1 C8 121.6(2)
C5 N1 C8 112.6(2)
O1 C1 N1 119.8(3)
O1 C1 C2 120.1(3)
N1 C1 C2 120.1(2)
C1 C2 C3 119.2(2)
C4 C3 C2 108.3(2)
C4 C3 C10 111.9(2)
C2 C3 C10 111.7(2)
C3 C4 C5 113.5(2)
N1 C5 C4 111.0(2)
N1 C5 C9 108.5(2)
C4 C5 C9 111.8(2)
N1 C5 C6 102.80(19)
C4 C5 C6 112.8(2)
C9 C5 C6 109.6(2)
C7 C6 C5 105.8(2)
C8 C7 C6 106.4(2)
N1 C8 C7 105.8(2)
F3 C9 F2 106.9(2)
F3 C9 F1 105.3(2)
F2 C9 F1 105.4(3)
F3 C9 C5 112.4(3)
F2 C9 C5 113.2(2)
F1 C9 C5 113.0(2)
C11 C10 C12 109.5(3)
C11 C10 C3 112.3(2)
C12 C10 C3 111.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C9 1.350(4)
F2 C9 1.332(3)
F3 C9 1.329(3)
N1 C1 1.341(3)
N1 C5 1.460(3)
N1 C8 1.467(3)
C1 O1 1.237(3)
C1 C2 1.488(4)
C2 C3 1.532(3)
C3 C4 1.520(3)
C3 C10 1.533(3)
C4 C5 1.520(3)
C5 C9 1.525(4)
C5 C6 1.536(4)
C6 C7 1.527(4)
C7 C8 1.499(5)
C10 C11 1.526(4)
C10 C12 1.529(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651833
