#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/48/7114867.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_7114867
loop_
_publ_author_name
'Katagiri, Toshimasa'
'Yamaji, Sachiko'
'Handa, Michiharu'
'Irie, Minoru'
'Uneyama, Kenji'
_publ_contact_author             'Dr Kenji Uneyama'
_publ_section_title
;
 Diastereoselectivity controlled by electrostatic repulsion between the
 negative charge on a trifluoromethyl group and that on aromatic
 ringsElectronic supplementary information (ESI) available: general
 experimental methods and typical reaction procedure. See
 http://www.rsc.org/suppdata/cc/b1/b105602f/
;
_journal_issue                   20
_journal_name_full               'Chemical Communications'
_journal_page_first              2054
_journal_paper_doi               10.1039/b105602f
_journal_year                    2001
_chemical_formula_moiety         'C11 H3 F8 N '
_chemical_formula_sum            'C11 H3 F8 N'
_chemical_formula_weight         301.14
_space_group_IT_number           146
_symmetry_cell_setting           rhombohedral
_symmetry_Int_Tables_number      146
_symmetry_space_group_name_Hall  'P 3*'
_symmetry_space_group_name_H-M   'R 3 :R'
_audit_creation_date             'Mon Aug 28 17:20:05 2001'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                111.8530(4)
_cell_angle_beta                 111.8530(4)
_cell_angle_gamma                111.8530(4)
_cell_formula_units_Z            3
_cell_length_a                   10.6401(4)
_cell_length_b                   10.6401(4)
_cell_length_c                   10.6401(4)
_cell_measurement_reflns_used    6053
_cell_measurement_temperature    150.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     835.60(6)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        teXsan
_computing_publication_material  teXsan
_computing_structure_refinement  teXsan
_diffrn_ambient_temperature      150.2
_diffrn_measurement_device       'Rigaku RAXIS-IV'
_diffrn_orient_matrix_UB_11      -0.03643
_diffrn_orient_matrix_UB_12      0.04003
_diffrn_orient_matrix_UB_13      0.07077
_diffrn_orient_matrix_UB_21      -0.03176
_diffrn_orient_matrix_UB_22      -0.09914
_diffrn_orient_matrix_UB_23      0.00337
_diffrn_orient_matrix_UB_31      0.11609
_diffrn_orient_matrix_UB_32      0.06620
_diffrn_orient_matrix_UB_33      0.10389
_diffrn_radiation_detector       'Imaging Plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_av_sigmaI/netI    0.058
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1281
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         54.90
_diffrn_reflns_theta_min         0.00
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             444.00
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.411
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     196
_refine_ls_number_reflns         1236
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0321
_refine_ls_shift/esd_max         0.0030
_refine_ls_shift/esd_mean        0.0010
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00002|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0308
_reflns_number_observed          1236
_reflns_number_total             1281
_reflns_observed_criterion       >0.8sigma(I)
_cod_data_source_file            b105602f.txt
_cod_data_source_block           katagiri_3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(Fo) +
0.00002|Fo|^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1/[\s^2^(Fo) + 0.00002|Fo|^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'R 3'
_cod_original_formula_sum        'C11 H3 F8 N '
_cod_database_code               7114867
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
z,x,y
y,z,x
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_refinement_flags
F(1) 0.7539 0.3504 0.2188 0.0305(5) Uani d 1.00 S
F(2) 0.8901(3) 0.6086(3) 0.5247(3) 0.0405(5) Uani d 1.00 .
F(3) 0.7824(3) 0.5592(3) 0.7090(3) 0.0441(6) Uani d 1.00 .
F(4) 0.5498(3) 0.2436(3) 0.5902(3) 0.0398(6) Uani d 1.00 .
F(5) 0.4075(3) -0.0189(3) 0.2788(3) 0.0262(5) Uani d 1.00 .
F(6) 0.3280(3) 0.1775(3) 0.0361(3) 0.0331(5) Uani d 1.00 .
F(7) 0.1520(3) -0.0348(3) 0.0090(3) 0.0401(7) Uani d 1.00 .
F(8) 0.1035(3) -0.0390(3) -0.2081(3) 0.0327(5) Uani d 1.00 .
N(1) 0.5322(4) -0.2148(4) 0.0742(4) 0.0282(7) Uani d 1.00 .
C(1) 0.4864(4) 0.0062(4) 0.0640(4) 0.0176(7) Uani d 1.00(1) .
C(2) 0.4609(4) 0.0147(4) -0.0822(4) 0.0240(8) Uani d 1.02(1) .
C(3) 0.3105(4) -0.0711(4) -0.0852(4) 0.0199(8) Uani d 1.02(1) .
C(4) 0.5711(4) 0.1570(4) 0.2358(4) 0.0201(8) Uani d 1.04(1) .
C(5) 0.5250(4) 0.1361(4) 0.3373(4) 0.0198(7) Uani d 1.00(1) .
C(6) 0.5951(4) 0.2690(4) 0.4951(4) 0.0263(8) Uani d 1.00(1) .
C(7) 0.7166(5) 0.4297(5) 0.5571(4) 0.0291(8) Uani d 1.00 .
C(8) 0.7688(4) 0.4546(4) 0.4631(4) 0.0277(7) Uani d 1.00 .
C(9) 0.6975(4) 0.3196(4) 0.3047(4) 0.0218(7) Uani d 1.00 .
C(10) 0.2244(4) 0.0086(4) -0.0611(4) 0.0219(7) Uani d 1.00 .
C(11) 0.5116(4) -0.1181(4) 0.0679(4) 0.0205(7) Uani d 1.00 .
H(1) 0.229(5) -0.198(5) -0.163(5) 0.037(10) Uiso calc 1.00 .
H(2) 0.494(4) 0.131(5) -0.058(4) 0.031(9) Uiso calc 1.00 .
H(3) 0.479(4) -0.058(5) -0.160(4) 0.032(9) Uiso calc 1.00 .
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 33 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0 9 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
F 0 24 0.017 0.010
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N 0 3 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(2) C(1) C(3) 58.7(2) 1_555 1_555 1_555 yes
C(2) C(1) C(4) 122.9(2) 1_555 1_555 1_555 yes
C(2) C(1) C(11) 117.1(2) 1_555 1_555 1_555 yes
C(3) C(1) C(4) 121.4(2) 1_555 1_555 1_555 yes
C(3) C(1) C(11) 113.7(2) 1_555 1_555 1_555 yes
C(4) C(1) C(11) 112.8(2) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 61.3(2) 1_555 1_555 1_555 yes
C(1) C(2) H(2) 114(1) 1_555 1_555 1_555 no
C(1) C(2) H(3) 115(2) 1_555 1_555 1_555 no
C(3) C(2) H(2) 111(2) 1_555 1_555 1_555 no
C(3) C(2) H(3) 118(1) 1_555 1_555 1_555 no
H(2) C(2) H(3) 120(2) 1_555 1_555 1_555 no
C(1) C(3) C(2) 60.0(2) 1_555 1_555 1_555 yes
C(1) C(3) C(10) 119.8(2) 1_555 1_555 1_555 yes
C(1) C(3) H(1) 116(2) 1_555 1_555 1_555 no
C(2) C(3) C(10) 120.1(3) 1_555 1_555 1_555 yes
C(2) C(3) H(1) 119(2) 1_555 1_555 1_555 no
C(10) C(3) H(1) 111(2) 1_555 1_555 1_555 no
C(1) C(4) C(5) 119.2(2) 1_555 1_555 1_555 yes
C(1) C(4) C(9) 124.3(3) 1_555 1_555 1_555 yes
C(5) C(4) C(9) 116.5(3) 1_555 1_555 1_555 yes
F(5) C(5) C(4) 118.9(3) 1_555 1_555 1_555 yes
F(5) C(5) C(6) 118.6(3) 1_555 1_555 1_555 yes
C(4) C(5) C(6) 122.5(3) 1_555 1_555 1_555 yes
F(4) C(6) C(5) 120.8(3) 1_555 1_555 1_555 yes
F(4) C(6) C(7) 120.0(3) 1_555 1_555 1_555 yes
C(5) C(6) C(7) 119.2(3) 1_555 1_555 1_555 yes
F(3) C(7) C(6) 119.3(3) 1_555 1_555 1_555 yes
F(3) C(7) C(8) 120.8(3) 1_555 1_555 1_555 yes
C(6) C(7) C(8) 119.9(3) 1_555 1_555 1_555 yes
F(2) C(8) C(7) 120.2(3) 1_555 1_555 1_555 yes
F(2) C(8) C(9) 119.7(3) 1_555 1_555 1_555 yes
C(7) C(8) C(9) 120.1(3) 1_555 1_555 1_555 yes
F(1) C(9) C(4) 120.6(2) 1_555 1_555 1_555 yes
F(1) C(9) C(8) 117.8(3) 1_555 1_555 1_555 yes
C(4) C(9) C(8) 121.6(3) 1_555 1_555 1_555 yes
F(6) C(10) F(7) 107.3(3) 1_555 1_555 1_555 yes
F(6) C(10) F(8) 106.2(2) 1_555 1_555 1_555 yes
F(6) C(10) C(3) 113.3(2) 1_555 1_555 1_555 yes
F(7) C(10) F(8) 107.2(2) 1_555 1_555 1_555 yes
F(7) C(10) C(3) 111.5(2) 1_555 1_555 1_555 yes
F(8) C(10) C(3) 111.0(2) 1_555 1_555 1_555 yes
N(1) C(11) C(1) 178.6(3) 1_555 1_555 1_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F(1) C(9) 1.338(3) 1_555 1_555 yes
F(2) C(8) 1.333(3) 1_555 1_555 yes
F(3) C(7) 1.335(4) 1_555 1_555 yes
F(4) C(6) 1.341(4) 1_555 1_555 yes
F(5) C(5) 1.339(3) 1_555 1_555 yes
F(6) C(10) 1.344(3) 1_555 1_555 yes
F(7) C(10) 1.334(4) 1_555 1_555 yes
F(8) C(10) 1.336(3) 1_555 1_555 yes
N(1) C(11) 1.148(4) 1_555 1_555 yes
C(1) C(2) 1.520(4) 1_555 1_555 yes
C(1) C(3) 1.540(4) 1_555 1_555 yes
C(1) C(4) 1.497(4) 1_555 1_555 yes
C(1) C(11) 1.456(4) 1_555 1_555 yes
C(2) C(3) 1.500(4) 1_555 1_555 yes
C(3) C(10) 1.489(4) 1_555 1_555 yes
C(4) C(5) 1.396(4) 1_555 1_555 yes
C(4) C(9) 1.388(4) 1_555 1_555 yes
C(5) C(6) 1.375(4) 1_555 1_555 yes
C(6) C(7) 1.382(5) 1_555 1_555 yes
C(7) C(8) 1.372(5) 1_555 1_555 yes
C(8) C(9) 1.383(4) 1_555 1_555 yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F(1) F(5) 3.057(2) 1_555 3_655
F(1) F(4) 3.206(2) 1_555 2_555
F(1) F(6) 3.272(2) 1_555 2_655
F(1) F(8) 3.293(2) 1_555 2_655
F(1) C(2) 3.513(3) 1_555 2_655
F(2) F(8) 2.867(2) 1_555 1_666
F(2) F(4) 3.088(3) 1_555 2_555
F(2) F(3) 3.153(3) 1_555 2_555
F(2) N(1) 3.317(3) 1_555 2_656
F(2) C(2) 3.482(4) 1_555 3_665
F(3) N(1) 3.057(4) 1_555 2_656
F(3) F(8) 3.191(3) 1_555 3_666
F(3) C(11) 3.248(4) 1_555 2_656
F(3) F(7) 3.473(3) 1_555 1_666
F(3) F(3) 3.473(4) 1_555 2_555
F(3) F(3) 3.473(4) 1_555 3_555
F(4) F(6) 3.005(3) 1_555 3_555
F(4) C(8) 3.159(4) 1_555 3_555
F(4) C(9) 3.231(4) 1_555 3_555
F(5) F(6) 2.898(3) 1_555 3_555
F(5) C(9) 3.059(3) 1_555 2_545
F(5) N(1) 3.374(3) 1_555 3_655
F(5) C(4) 3.484(3) 1_555 2_545
F(5) C(8) 3.502(4) 1_555 2_545
F(6) F(7) 3.069(3) 1_555 2_555
F(6) C(5) 3.396(3) 1_555 2_555
F(6) C(6) 3.419(4) 1_555 2_555
F(7) F(8) 2.941(3) 1_555 3_555
F(7) F(7) 2.983(3) 1_555 2_555
F(7) F(7) 2.983(3) 1_555 3_555
F(7) C(10) 3.228(4) 1_555 3_555
F(8) C(2) 3.082(4) 1_555 3_554
N(1) C(7) 3.102(4) 1_555 3_544
N(1) C(5) 3.241(4) 1_555 2_545
N(1) C(8) 3.255(4) 1_555 3_544
N(1) C(3) 3.351(4) 1_555 3_655
N(1) C(6) 3.417(4) 1_555 2_545
N(1) C(11) 3.592(4) 1_555 3_655
C(7) C(11) 3.520(4) 1_555 2_656
