#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/75/2207582.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2207582
loop_
_publ_author_name
'Tang, Riyuan'
'Zhong, Ping'
'Lin, Qiulian'
'Hu, Maolin'
'Shi, Qian'
_publ_section_title
5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)-1H-pyrazole-3-carbonitrile
_journal_coeditor_code           KP6064
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4374
_journal_page_last               o4375
_journal_paper_doi               10.1107/S1600536805039280
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C12 H4 Cl2 F6 N4 S'
_chemical_formula_moiety         'C12 H4 Cl2 F6 N4 S'
_chemical_formula_sum            'C12 H4 Cl2 F6 N4 S'
_chemical_formula_weight         421.16
_chemical_melting_point          434.0(10)
_chemical_name_systematic
;
5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-
4-(trifluoromethylsulfanyl)-1H-pyrazole-3-carbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.9730(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7801(8)
_cell_length_b                   12.7006(9)
_cell_length_c                   12.1039(9)
_cell_measurement_reflns_used    3781
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.32
_cell_volume                     1644.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8518
_diffrn_reflns_theta_full        25.22
_diffrn_reflns_theta_max         25.22
_diffrn_reflns_theta_min         2.33
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  0.8866
_exptl_absorpt_correction_T_min  0.7905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.259
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.059P)²+0.9497P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                2636
_reflns_number_total             2953
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp6064.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      'P 21/n'
_cod_database_code               2207582
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Cl1 1.17081(7) 0.08140(6) 0.57001(6) 0.0642(2) Uani d . 1 Cl
Cl2 0.77652(7) 0.31669(7) 0.40429(7) 0.0773(3) Uani d . 1 Cl
S1 1.05416(7) 0.41352(7) 0.84033(6) 0.0664(2) Uani d . 1 S
F1 1.0052(3) 0.60601(19) 0.8706(2) 0.1317(10) Uani d . 1 F
F2 0.852(2) 0.516(2) 0.830(2) 0.128(7) Uani d P 0.50 F
F2' 0.841(2) 0.5160(19) 0.788(2) 0.116(6) Uani d P 0.50 F
F3 0.9607(13) 0.5570(11) 0.7024(10) 0.119(4) Uani d P 0.50 F
F3' 0.9846(13) 0.5642(12) 0.7017(12) 0.116(5) Uani d P 0.50 F
F4 1.0293(15) 0.1466(7) 0.0813(8) 0.120(4) Uani d P 0.50 F
F4' 0.9506(19) 0.1303(13) 0.0777(5) 0.166(7) Uani d P 0.50 F
F5 1.1159(10) 0.0611(16) 0.1334(9) 0.147(6) Uani d P 0.50 F
F5' 1.0824(13) 0.0015(11) 0.1475(7) 0.121(5) Uani d P 0.50 F
F6 0.8933(7) 0.0364(11) 0.1036(7) 0.105(2) Uani d P 0.50 F
F6' 0.9570(19) -0.0224(10) 0.1410(9) 0.157(4) Uani d P 0.50 F
N1 0.7652(3) 0.2128(2) 0.8963(2) 0.0742(8) Uani d . 1 N
N2 0.8823(2) 0.19271(17) 0.64758(18) 0.0528(5) Uani d . 1 N
N3 0.96566(19) 0.23574(17) 0.58307(16) 0.0476(5) Uani d . 1 N
N4 1.1189(2) 0.3691(2) 0.5841(2) 0.0665(7) Uani d D 1 N
C1 0.9642(3) 0.5287(3) 0.8031(3) 0.0764(9) Uani d . 1 C
C2 0.9915(2) 0.3283(2) 0.73624(19) 0.0473(6) Uani d . 1 C
C3 0.8993(2) 0.2506(2) 0.7390(2) 0.0483(6) Uani d . 1 C
C4 1.0329(2) 0.3159(2) 0.63280(19) 0.0461(6) Uani d . 1 C
C5 0.8250(3) 0.2289(2) 0.8273(2) 0.0559(7) Uani d . 1 C
C6 0.9741(2) 0.19387(19) 0.47544(19) 0.0433(5) Uani d . 1 C
C7 1.0653(2) 0.1209(2) 0.45895(19) 0.0439(5) Uani d . 1 C
C8 1.0749(2) 0.0802(2) 0.3545(2) 0.0474(6) Uani d . 1 C
H8 1.1357 0.0305 0.3440 0.057 Uiso calc R 1 H
C9 0.9923(2) 0.1149(2) 0.2663(2) 0.0491(6) Uani d . 1 C
C10 0.9004(2) 0.1872(2) 0.2804(2) 0.0527(6) Uani d . 1 C
H10 0.8452 0.2096 0.2200 0.063 Uiso calc R 1 H
C11 0.8914(2) 0.2260(2) 0.3853(2) 0.0493(6) Uani d . 1 C
C12 1.0025(4) 0.0728(3) 0.1517(3) 0.0709(9) Uani d . 1 C
H4A 1.145(3) 0.347(3) 0.525(2) 0.085 Uiso d D 1 H
H4B 1.144(3) 0.4243(19) 0.615(3) 0.085 Uiso d D 1 H
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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
C2 S1 C1 100.16(15) yes
F2' F2 C1 81(5) ?
F2 F2' C1 76(5) ?
F4' F4 C12 64.8(9) ?
F4' F4 F5 113.5(13) ?
C12 F4 F5 52.9(5) ?
F4 F4' C12 75.6(10) ?
F4 F4' F6 130.4(14) ?
C12 F4' F6 60.4(6) ?
F5' F5 C12 68.6(10) ?
F5' F5 F4 117.2(14) ?
C12 F5 F4 55.6(5) ?
F5 F5' C12 71.4(9) ?
F5 F5' F6' 127.7(14) ?
C12 F5' F6' 59.2(6) ?
F6' F6 C12 64.7(6) ?
F6' F6 F4' 114.2(9) ?
C12 F6 F4' 53.8(5) ?
F6 F6' C12 67.1(8) ?
F6 F6' F5' 116.3(10) ?
C12 F6' F5' 55.7(5) ?
C3 N2 N3 102.7(2) yes
C4 N3 N2 113.58(19) yes
C4 N3 C6 126.99(19) yes
N2 N3 C6 119.44(19) yes
C4 N4 H4A 122(2) ?
C4 N4 H4B 116(3) ?
H4A N4 H4B 123(3) yes
F3 C1 F2 111.0(13) yes
F3 C1 F1 110.7(7) yes
F2 C1 F1 100.7(13) yes
F3 C1 F2' 89.4(13) ?
F2 C1 F2' 22(2) ?
F1 C1 F2' 115.4(12) ?
F3 C1 F3' 11.5(11) ?
F2 C1 F3' 122.0(13) ?
F1 C1 F3' 103.6(8) ?
F2' C1 F3' 100.7(12) ?
F3 C1 S1 115.4(7) ?
F2 C1 S1 109.2(11) ?
F1 C1 S1 108.8(3) ?
F2' C1 S1 116.1(10) ?
F3' C1 S1 111.1(7) ?
C4 C2 C3 104.4(2) yes
C4 C2 S1 125.86(19) yes
C3 C2 S1 129.47(18) yes
N2 C3 C2 113.4(2) ?
N2 C3 C5 118.8(2) ?
C2 C3 C5 127.8(2) ?
N4 C4 N3 123.2(2) yes
N4 C4 C2 130.9(2) yes
N3 C4 C2 105.9(2) ?
N1 C5 C3 179.0(3) yes
C11 C6 C7 119.0(2) yes
C11 C6 N3 120.4(2) yes
C7 C6 N3 120.6(2) yes
C8 C7 C6 121.1(2) yes
C8 C7 Cl1 119.27(19) yes
C6 C7 Cl1 119.66(18) ?
C9 C8 C7 118.5(2) ?
C9 C8 H8 120.7 yes
C7 C8 H8 120.7 ?
C10 C9 C8 121.6(2) yes
C10 C9 C12 119.1(3) yes
C8 C9 C12 119.3(2) ?
C11 C10 C9 119.1(2) ?
C11 C10 H10 120.5 ?
C9 C10 H10 120.5 ?
C10 C11 C6 120.7(2) yes
C10 C11 Cl2 119.6(2) ?
C6 C11 Cl2 119.70(19) ?
F4' C12 F5' 130.6(6) ?
F4' C12 F5 107.5(8) ?
F5' C12 F5 40.0(6) ?
F4' C12 F6' 110.1(8) ?
F5' C12 F6' 65.1(7) ?
F5 C12 F6' 103.4(7) ?
F4' C12 F4 39.6(8) ?
F5' C12 F4 106.3(7) ?
F5 C12 F4 71.4(7) yes
F6' C12 F4 134.6(6) ?
F4' C12 F6 65.8(8) ?
F5' C12 F6 107.8(6) ?
F5 C12 F6 134.2(6) ?
F6' C12 F6 48.2(6) yes
F4 C12 F6 102.5(6) ?
F4' C12 C9 112.4(5) ?
F5' C12 C9 114.9(4) ?
F5 C12 C9 112.3(6) yes
F6' C12 C9 110.7(4) ?
F4 C12 C9 112.9(5) ?
F6 C12 C9 111.6(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C7 1.726(2) yes
Cl2 C11 1.727(3) yes
S1 C2 1.735(3) yes
S1 C1 1.783(4) yes
F1 C1 1.319(4) ?
F2 F2' 0.51(5) ?
F2 C1 1.30(2) ?
F2' C1 1.33(2) ?
F3 C1 1.266(11) yes
F3' C1 1.350(12) ?
F4 F4' 0.869(16) ?
F4 C12 1.321(8) yes
F4 F5 1.517(15) ?
F4' C12 1.235(9) ?
F4' F6 1.396(16) ?
F5 F5' 0.866(12) ?
F5 C12 1.277(10) ?
F5' C12 1.255(8) ?
F5' F6' 1.378(13) ?
F6 F6' 1.077(13) ?
F6 C12 1.331(7) ?
F6' C12 1.306(8) ?
N1 C5 1.135(3) yes
N2 C3 1.323(3) yes
N2 N3 1.374(3) yes
N3 C4 1.349(3) yes
N3 C6 1.420(3) yes
N4 C4 1.340(3) yes
N4 H4A 0.848(18) ?
N4 H4B 0.828(18) ?
C2 C4 1.388(3) ?
C2 C3 1.403(4) ?
C3 C5 1.438(3) yes
C6 C11 1.383(4) yes
C6 C7 1.384(3) yes
C7 C8 1.381(3) ?
C8 C9 1.377(4) yes
C8 H8 0.9300 yes
C9 C10 1.377(4) ?
C9 C12 1.503(4) yes
C10 C11 1.376(4) ?
C10 H10 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N4 H4A N1 4_665 0.848(18) 2.27(2) 3.099(3) 164(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
F5 F4 F4' C12 21.6(10)
C12 F4 F4' F6 -27.4(11)
F5 F4 F4' F6 -6(2)
F4' F4 F5 F5' 7(2)
C12 F4 F5 F5' 32.0(12)
F4' F4 F5 C12 -24.7(11)
F4 F5 F5' C12 -28.0(10)
C12 F5 F5' F6' 19.6(13)
F4 F5 F5' F6' -8(2)
F4 F4' F6 F6' 6.4(18)
C12 F4' F6 F6' -24.5(7)
F4 F4' F6 C12 30.8(13)
F4' F6 F6' C12 21.7(6)
C12 F6 F6' F5' -27.1(6)
F4' F6 F6' F5' -5.4(11)
F5 F5' F6' F6 9(2)
C12 F5' F6' F6 30.6(7)
F5 F5' F6' C12 -21.7(15)
C3 N2 N3 C4 0.8(3)
C3 N2 N3 C6 -179.5(2)
F2' F2 C1 F3 16(6)
F2' F2 C1 F1 134(5)
F2' F2 C1 F3' 20(6)
F2' F2 C1 S1 -112(5)
F2 F2' C1 F3 -165(5)
F2 F2' C1 F1 -52(6)
F2 F2' C1 F3' -163(5)
F2 F2' C1 S1 77(6)
C2 S1 C1 F3 -50.9(8)
C2 S1 C1 F2 74.9(13)
C2 S1 C1 F1 -176.0(2)
C2 S1 C1 F2' 51.7(13)
C2 S1 C1 F3' -62.6(7)
C1 S1 C2 C4 89.0(3)
C1 S1 C2 C3 -98.0(3)
N3 N2 C3 C2 -0.7(3)
N3 N2 C3 C5 179.2(2)
C4 C2 C3 N2 0.4(3)
S1 C2 C3 N2 -173.8(2)
C4 C2 C3 C5 -179.5(3)
S1 C2 C3 C5 6.3(4)
N2 N3 C4 N4 -179.7(3)
C6 N3 C4 N4 0.7(4)
N2 N3 C4 C2 -0.6(3)
C6 N3 C4 C2 179.8(2)
C3 C2 C4 N4 179.1(3)
S1 C2 C4 N4 -6.4(4)
C3 C2 C4 N3 0.1(3)
S1 C2 C4 N3 174.58(19)
N2 C3 C5 N1 -9E1(2)
C2 C3 C5 N1 9E1(2)
C4 N3 C6 C11 -97.0(3)
N2 N3 C6 C11 83.4(3)
C4 N3 C6 C7 82.6(3)
N2 N3 C6 C7 -97.0(3)
C11 C6 C7 C8 0.1(4)
N3 C6 C7 C8 -179.5(2)
C11 C6 C7 Cl1 179.00(19)
N3 C6 C7 Cl1 -0.7(3)
C6 C7 C8 C9 0.8(4)
Cl1 C7 C8 C9 -178.04(19)
C7 C8 C9 C10 -1.1(4)
C7 C8 C9 C12 179.1(3)
C8 C9 C10 C11 0.3(4)
C12 C9 C10 C11 -179.8(3)
C9 C10 C11 C6 0.7(4)
C9 C10 C11 Cl2 180.0(2)
C7 C6 C11 C10 -0.9(4)
N3 C6 C11 C10 178.8(2)
C7 C6 C11 Cl2 179.78(19)
N3 C6 C11 Cl2 -0.6(3)
F4 F4' C12 F5' -63.0(16)
F6 F4' C12 F5' 93.3(10)
F4 F4' C12 F5 -24.9(13)
F6 F4' C12 F5 131.3(6)
F4 F4' C12 F6' -136.9(11)
F6 F4' C12 F6' 19.4(7)
F6 F4' C12 F4 156.2(12)
F4 F4' C12 F6 -156.2(12)
F4 F4' C12 C9 99.2(10)
F6 F4' C12 C9 -104.5(6)
F5 F5' C12 F4' 66.2(17)
F6' F5' C12 F4' -95.8(11)
F6' F5' C12 F5 -162.0(14)
F5 F5' C12 F6' 162.0(14)
F5 F5' C12 F4 30.0(13)
F6' F5' C12 F4 -132.1(7)
F5 F5' C12 F6 139.2(11)
F6' F5' C12 F6 -22.8(7)
F5 F5' C12 C9 -95.6(12)
F6' F5' C12 C9 102.3(5)
F5' F5 C12 F4' -133.2(12)
F4 F5 C12 F4' 16.5(9)
F4 F5 C12 F5' 149.6(13)
F5' F5 C12 F6' -16.7(13)
F4 F5 C12 F6' 132.9(6)
F5' F5 C12 F4 -149.6(13)
F5' F5 C12 F6 -60.2(16)
F4 F5 C12 F6 89.4(10)
F5' F5 C12 C9 102.6(11)
F4 F5 C12 C9 -107.8(6)
F6 F6' C12 F4' -23.9(8)
F5' F6' C12 F4' 126.4(7)
F6 F6' C12 F5' -150.3(8)
F6 F6' C12 F5 -138.6(8)
F5' F6' C12 F5 11.7(9)
F6 F6' C12 F4 -61.6(12)
F5' F6' C12 F4 88.7(11)
F5' F6' C12 F6 150.3(8)
F6 F6' C12 C9 101.0(6)
F5' F6' C12 C9 -108.7(5)
F5 F4 C12 F4' -154.9(13)
F4' F4 C12 F5' 135.1(11)
F5 F4 C12 F5' -19.8(8)
F4' F4 C12 F5 154.9(13)
F4' F4 C12 F6' 64.3(15)
F5 F4 C12 F6' -90.6(11)
F4' F4 C12 F6 22.1(11)
F5 F4 C12 F6 -132.8(6)
F4' F4 C12 C9 -98.0(11)
F5 F4 C12 C9 107.1(6)
F6' F6 C12 F4' 155.3(8)
F6' F6 C12 F5' 28.1(8)
F4' F6 C12 F5' -127.2(7)
F6' F6 C12 F5 64.0(12)
F4' F6 C12 F5 -91.3(11)
F4' F6 C12 F6' -155.3(8)
F6' F6 C12 F4 140.1(7)
F4' F6 C12 F4 -15.2(7)
F6' F6 C12 C9 -98.9(6)
F4' F6 C12 C9 105.8(5)
C10 C9 C12 F4' 20.1(13)
C8 C9 C12 F4' -160.1(13)
C10 C9 C12 F5' -174.8(10)
C8 C9 C12 F5' 5.1(11)
C10 C9 C12 F5 141.5(10)
C8 C9 C12 F5 -38.6(11)
C10 C9 C12 F6' -103.5(12)
C8 C9 C12 F6' 76.3(12)
C10 C9 C12 F4 63.1(9)
C8 C9 C12 F4 -117.1(8)
C10 C9 C12 F6 -51.6(8)
C8 C9 C12 F6 128.2(8)
