#------------------------------------------------------------------------------
#$Date: 2019-11-25 12:12:36 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240833 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/03/4130373.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_4130373
loop_
_publ_author_name
'Topić, Filip'
'Rissanen, Kari'
_publ_section_title
;
 Systematic Construction of Ternary Cocrystals by Orthogonal and Robust
 Hydrogen and Halogen Bonds.
;
_journal_issue                   20
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6610
_journal_page_last               6616
_journal_paper_doi               10.1021/jacs.6b02854
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C12 H24 O6, 2(C6 F5 I), C H4 N2 S'
_chemical_formula_sum            'C25 H28 F10 I2 N2 O6 S'
_chemical_formula_weight         928.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                107.2011(7)
_cell_angle_beta                 99.0307(8)
_cell_angle_gamma                95.8325(8)
_cell_formula_units_Z            2
_cell_length_a                   9.62660(10)
_cell_length_b                   12.1164(2)
_cell_length_c                   15.7630(2)
_cell_measurement_reflns_used    6856
_cell_measurement_temperature    253.0(1)
_cell_measurement_theta_max      27.103
_cell_measurement_theta_min      0.407
_cell_volume                     1713.10(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      253.0(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD with APEXII detector'
_diffrn_measurement_method       'φ scans + ω scans'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24889
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         1.781
_exptl_absorpt_coefficient_mu    1.990
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008 (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.035
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.0019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         7763
_refine_ls_number_restraints     634
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0321P)²+3.4461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5135
_reflns_number_total             7763
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b02854_si_002.cif
_cod_data_source_block           A_C_1-2_253K
_cod_database_code               4130373
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.534
_shelx_estimated_absorpt_t_max   0.826
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.1320(5) 0.2440(4) 0.4987(3) 0.0517(11) Uani 1 1 d . . . . .
N1A N 0.0511(4) 0.1418(4) 0.4628(3) 0.0662(12) Uani 1 1 d . . . . .
H1A1 H -0.0392 0.1360 0.4612 0.079 Uiso 1 1 calc R U . . .
H1A2 H 0.0881 0.0805 0.4408 0.079 Uiso 1 1 calc R U . . .
N2A N 0.0735(5) 0.3367(4) 0.5319(3) 0.0722(13) Uani 1 1 d . . . . .
H2A1 H -0.0169 0.3298 0.5298 0.087 Uiso 1 1 calc R U . . .
H2A2 H 0.1255 0.4044 0.5557 0.087 Uiso 1 1 calc R U . . .
S1A S 0.31190(13) 0.25838(11) 0.50013(9) 0.0570(3) Uani 1 1 d . . . . .
C1C C 0.0783(11) 0.1049(11) 0.7365(7) 0.088(3) Uani 0.647(10) 1 d D U P A 1
H1C1 H 0.1367 0.1510 0.7947 0.106 Uiso 0.647(10) 1 calc R U P A 1
H1C2 H 0.0339 0.0333 0.7434 0.106 Uiso 0.647(10) 1 calc R U P A 1
C2C C 0.2776(15) 0.0220(14) 0.6971(7) 0.094(3) Uani 0.647(10) 1 d D U P A 1
H2C1 H 0.2428 -0.0478 0.7105 0.113 Uiso 0.647(10) 1 calc R U P A 1
H2C2 H 0.3422 0.0740 0.7509 0.113 Uiso 0.647(10) 1 calc R U P A 1
C3C C 0.3523(12) -0.0093(13) 0.6242(7) 0.094(3) Uani 0.647(10) 1 d D U P A 1
H3C1 H 0.3848 0.0605 0.6102 0.113 Uiso 0.647(10) 1 calc R U P A 1
H3C2 H 0.4356 -0.0414 0.6432 0.113 Uiso 0.647(10) 1 calc R U P A 1
C4C C 0.3315(9) -0.0929(9) 0.4713(5) 0.076(2) Uani 0.647(10) 1 d D U P A 1
H4C1 H 0.4194 -0.1250 0.4773 0.091 Uiso 0.647(10) 1 calc R U P A 1
H4C2 H 0.3550 -0.0134 0.4707 0.091 Uiso 0.647(10) 1 calc R U P A 1
C5C C 0.2388(9) -0.1619(8) 0.3859(6) 0.075(2) Uani 0.647(10) 1 d D U P A 1
H5C1 H 0.2925 -0.1735 0.3376 0.091 Uiso 0.647(10) 1 calc R U P A 1
H5C2 H 0.2036 -0.2380 0.3893 0.091 Uiso 0.647(10) 1 calc R U P A 1
C6C C 0.0310(14) -0.1686(13) 0.2860(9) 0.088(4) Uani 0.647(10) 1 d D U P A 1
H6C1 H -0.0123 -0.2414 0.2914 0.106 Uiso 0.647(10) 1 calc R U P A 1
H6C2 H 0.0841 -0.1876 0.2375 0.106 Uiso 0.647(10) 1 calc R U P A 1
O1C O 0.1645(12) 0.0766(13) 0.6756(7) 0.088(3) Uani 0.647(10) 1 d D U P A 1
O2C O 0.2692(13) -0.0908(10) 0.5463(5) 0.078(3) Uani 0.647(10) 1 d D U P A 1
O3C O 0.1241(10) -0.1054(8) 0.3666(8) 0.076(3) Uani 0.647(10) 1 d D U P A 1
C1C' C 0.0981(16) 0.1475(19) 0.7155(13) 0.092(6) Uani 0.353(10) 1 d D U P A 2
H1C3 H 0.1590 0.2225 0.7321 0.111 Uiso 0.353(10) 1 calc R U P A 2
H1C4 H 0.1067 0.1225 0.7689 0.111 Uiso 0.353(10) 1 calc R U P A 2
C2C' C 0.279(2) 0.034(2) 0.6722(11) 0.090(5) Uani 0.353(10) 1 d D U P A 2
H2C3 H 0.2689 -0.0183 0.7076 0.108 Uiso 0.353(10) 1 calc R U P A 2
H2C4 H 0.3471 0.1027 0.7097 0.108 Uiso 0.353(10) 1 calc R U P A 2
C3C' C 0.336(2) -0.023(2) 0.5945(13) 0.082(4) Uani 0.353(10) 1 d D U P A 2
H3C3 H 0.3585 0.0331 0.5640 0.099 Uiso 0.353(10) 1 calc R U P A 2
H3C4 H 0.4245 -0.0476 0.6153 0.099 Uiso 0.353(10) 1 calc R U P A 2
C4C' C 0.2993(18) -0.1595(14) 0.4521(10) 0.070(3) Uani 0.353(10) 1 d D U P A 2
H4C3 H 0.2519 -0.2388 0.4191 0.084 Uiso 0.353(10) 1 calc R U P A 2
H4C4 H 0.4002 -0.1621 0.4675 0.084 Uiso 0.353(10) 1 calc R U P A 2
C5C' C 0.2789(15) -0.0883(15) 0.3937(10) 0.075(3) Uani 0.353(10) 1 d D U P A 2
H5C3 H 0.3374 -0.0122 0.4229 0.090 Uiso 0.353(10) 1 calc R U P A 2
H5C4 H 0.3102 -0.1246 0.3378 0.090 Uiso 0.353(10) 1 calc R U P A 2
C6C' C 0.0461(19) -0.165(2) 0.308(2) 0.086(6) Uani 0.353(10) 1 d D U P A 2
H6C3 H 0.0447 -0.2328 0.3285 0.104 Uiso 0.353(10) 1 calc R U P A 2
H6C4 H 0.0856 -0.1828 0.2535 0.104 Uiso 0.353(10) 1 calc R U P A 2
O1C' O 0.149(2) 0.069(2) 0.6506(11) 0.075(4) Uani 0.353(10) 1 d D U P A 2
O2C' O 0.248(2) -0.1199(18) 0.5320(10) 0.068(3) Uani 0.353(10) 1 d D U P A 2
O3C' O 0.1373(18) -0.0734(15) 0.3734(16) 0.075(4) Uani 0.353(10) 1 d D U P A 2
C1D C 0.0934(8) 0.6148(6) 0.7516(4) 0.090(2) Uani 1 1 d . . . . .
H1D1 H 0.0390 0.6753 0.7434 0.108 Uiso 1 1 calc R U . . .
H1D2 H 0.1588 0.6458 0.8096 0.108 Uiso 1 1 calc R U . . .
C2D C 0.2469(7) 0.6800(5) 0.6689(4) 0.0852(18) Uani 1 1 d . U . . .
H2D1 H 0.3121 0.7252 0.7248 0.102 Uiso 1 1 calc R U . . .
H2D2 H 0.1815 0.7297 0.6529 0.102 Uiso 1 1 calc R U . . .
C3D C 0.3279(7) 0.6388(6) 0.5953(5) 0.0875(18) Uani 1 1 d . U . . .
H3D1 H 0.3877 0.7048 0.5898 0.105 Uiso 1 1 calc R U . . .
H3D2 H 0.3886 0.5849 0.6094 0.105 Uiso 1 1 calc R U . . .
C4D C 0.3016(6) 0.5419(6) 0.4406(4) 0.0783(16) Uani 1 1 d . U . . .
H4D1 H 0.3700 0.4939 0.4559 0.094 Uiso 1 1 calc R U . . .
H4D2 H 0.3527 0.6078 0.4295 0.094 Uiso 1 1 calc R U . . .
C5D C 0.1964(7) 0.4727(5) 0.3587(4) 0.0721(15) Uani 1 1 d . U . . .
H5D1 H 0.2452 0.4392 0.3101 0.086 Uiso 1 1 calc R U . . .
H5D2 H 0.1423 0.4090 0.3710 0.086 Uiso 1 1 calc R U . . .
C6D C 0.0054(8) 0.4904(6) 0.2499(4) 0.0855(19) Uani 1 1 d . . . . .
H6D1 H 0.0584 0.4669 0.2017 0.103 Uiso 1 1 calc R U . . .
H6D2 H -0.0514 0.5474 0.2370 0.103 Uiso 1 1 calc R U . . .
O1D O 0.1704(4) 0.5818(3) 0.6811(3) 0.0751(11) Uani 1 1 d . . . . .
O2D O 0.2304(4) 0.5826(3) 0.5134(3) 0.0685(10) Uani 1 1 d . . . . .
O3D O 0.1027(4) 0.5448(3) 0.3319(3) 0.0695(10) Uani 1 1 d . . . . .
C1S C 0.2642(7) 0.0848(5) 0.1444(4) 0.0745(15) Uani 1 1 d . U . . .
C2S C 0.3310(9) -0.0056(7) 0.1059(5) 0.106(2) Uani 1 1 d . U . . .
C3S C 0.3104(11) -0.0544(8) 0.0134(6) 0.126(3) Uani 1 1 d . U . . .
C4S C 0.2225(10) -0.0134(8) -0.0417(5) 0.116(3) Uani 1 1 d . U . . .
C5S C 0.1566(10) 0.0778(8) -0.0065(5) 0.112(3) Uani 1 1 d . U . . .
C6S C 0.1775(8) 0.1264(7) 0.0867(5) 0.095(2) Uani 1 1 d . U . . .
F1S F 0.4159(7) -0.0494(5) 0.1577(3) 0.164(3) Uani 1 1 d . U . . .
F2S F 0.3765(10) -0.1431(7) -0.0230(4) 0.225(4) Uani 1 1 d . U . . .
F3S F 0.1991(8) -0.0631(6) -0.1321(3) 0.178(3) Uani 1 1 d . U . . .
F4S F 0.0696(7) 0.1195(6) -0.0602(3) 0.167(2) Uani 1 1 d . U . . .
F5S F 0.1094(6) 0.2163(5) 0.1192(3) 0.142(2) Uani 1 1 d . U . . .
I1S I 0.28665(4) 0.15499(3) 0.28574(2) 0.06837(15) Uani 1 1 d . U . . .
C1T C 0.5745(7) 0.4532(6) 0.8473(4) 0.0765(16) Uani 1 1 d . U . . .
C2T C 0.6754(9) 0.3990(7) 0.8824(5) 0.101(2) Uani 1 1 d . U . . .
C3T C 0.7607(10) 0.4499(8) 0.9681(5) 0.120(3) Uani 1 1 d . U . . .
C4T C 0.7414(9) 0.5576(8) 1.0179(5) 0.109(2) Uani 1 1 d . U . . .
C5T C 0.6427(9) 0.6138(7) 0.9852(5) 0.106(2) Uani 1 1 d . U . . .
C6T C 0.5599(8) 0.5612(6) 0.9004(5) 0.093(2) Uani 1 1 d . U . . .
F1T F 0.6940(7) 0.2926(5) 0.8349(3) 0.161(2) Uani 1 1 d . U . . .
F2T F 0.8597(8) 0.3963(6) 1.0012(4) 0.194(3) Uani 1 1 d . U . . .
F3T F 0.8214(7) 0.6084(5) 1.1017(3) 0.167(2) Uani 1 1 d . U . . .
F4T F 0.6234(7) 0.7192(5) 1.0371(4) 0.165(2) Uani 1 1 d . U . . .
F5T F 0.4632(6) 0.6195(4) 0.8703(3) 0.149(2) Uani 1 1 d . U . . .
I1T I 0.45093(5) 0.37475(4) 0.71590(3) 0.08357(17) Uani 1 1 d . U . . .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
N1A C1A N2A 119.1(4) . .
N1A C1A S1A 120.8(4) . .
N2A C1A S1A 120.0(4) . .
C1A N1A H1A1 120.0 . .
C1A N1A H1A2 120.0 . .
H1A1 N1A H1A2 120.0 . .
C1A N2A H2A1 120.0 . .
C1A N2A H2A2 120.0 . .
H2A1 N2A H2A2 120.0 . .
O1C C1C C6C 115.3(9) . 2_556
O1C C1C H1C1 108.5 . .
C6C C1C H1C1 108.5 2_556 .
O1C C1C H1C2 108.5 . .
C6C C1C H1C2 108.5 2_556 .
H1C1 C1C H1C2 107.5 . .
O1C C2C C3C 111.0(8) . .
O1C C2C H2C1 109.4 . .
C3C C2C H2C1 109.4 . .
O1C C2C H2C2 109.4 . .
C3C C2C H2C2 109.4 . .
H2C1 C2C H2C2 108.0 . .
O2C C3C C2C 112.9(8) . .
O2C C3C H3C1 109.0 . .
C2C C3C H3C1 109.0 . .
O2C C3C H3C2 109.0 . .
C2C C3C H3C2 109.0 . .
H3C1 C3C H3C2 107.8 . .
O2C C4C C5C 112.7(7) . .
O2C C4C H4C1 109.1 . .
C5C C4C H4C1 109.1 . .
O2C C4C H4C2 109.1 . .
C5C C4C H4C2 109.1 . .
H4C1 C4C H4C2 107.8 . .
O3C C5C C4C 110.6(7) . .
O3C C5C H5C1 109.5 . .
C4C C5C H5C1 109.5 . .
O3C C5C H5C2 109.5 . .
C4C C5C H5C2 109.5 . .
H5C1 C5C H5C2 108.1 . .
O3C C6C C1C 112.0(8) . 2_556
O3C C6C H6C1 109.2 . .
C1C C6C H6C1 109.2 2_556 .
O3C C6C H6C2 109.2 . .
C1C C6C H6C2 109.2 2_556 .
H6C1 C6C H6C2 107.9 . .
C1C O1C C2C 117.5(10) . .
C3C O2C C4C 110.0(8) . .
C6C O3C C5C 112.9(7) . .
O1C' C1C' C6C' 116.9(10) . 2_556
O1C' C1C' H1C3 108.1 . .
C6C' C1C' H1C3 108.1 2_556 .
O1C' C1C' H1C4 108.1 . .
C6C' C1C' H1C4 108.1 2_556 .
H1C3 C1C' H1C4 107.3 . .
O1C' C2C' C3C' 113.6(11) . .
O1C' C2C' H2C3 108.8 . .
C3C' C2C' H2C3 108.8 . .
O1C' C2C' H2C4 108.8 . .
C3C' C2C' H2C4 108.8 . .
H2C3 C2C' H2C4 107.7 . .
O2C' C3C' C2C' 115.6(12) . .
O2C' C3C' H3C3 108.4 . .
C2C' C3C' H3C3 108.4 . .
O2C' C3C' H3C4 108.4 . .
C2C' C3C' H3C4 108.4 . .
H3C3 C3C' H3C4 107.5 . .
O2C' C4C' C5C' 114.0(11) . .
O2C' C4C' H4C3 108.8 . .
C5C' C4C' H4C3 108.8 . .
O2C' C4C' H4C4 108.8 . .
C5C' C4C' H4C4 108.8 . .
H4C3 C4C' H4C4 107.7 . .
O3C' C5C' C4C' 112.4(11) . .
O3C' C5C' H5C3 109.1 . .
C4C' C5C' H5C3 109.1 . .
O3C' C5C' H5C4 109.1 . .
C4C' C5C' H5C4 109.1 . .
H5C3 C5C' H5C4 107.9 . .
O3C' C6C' C1C' 117.2(10) . 2_556
O3C' C6C' H6C3 108.0 . .
C1C' C6C' H6C3 108.0 2_556 .
O3C' C6C' H6C4 108.0 . .
C1C' C6C' H6C4 108.0 2_556 .
H6C3 C6C' H6C4 107.3 . .
C1C' O1C' C2C' 120.3(11) . .
C3C' O2C' C4C' 112.2(12) . .
C6C' O3C' C5C' 117.2(12) . .
O1D C1D C6D 109.1(5) . 2_566
O1D C1D H1D1 109.9 . .
C6D C1D H1D1 109.9 2_566 .
O1D C1D H1D2 109.9 . .
C6D C1D H1D2 109.9 2_566 .
H1D1 C1D H1D2 108.3 . .
O1D C2D C3D 108.9(5) . .
O1D C2D H2D1 109.9 . .
C3D C2D H2D1 109.9 . .
O1D C2D H2D2 109.9 . .
C3D C2D H2D2 109.9 . .
H2D1 C2D H2D2 108.3 . .
O2D C3D C2D 108.8(5) . .
O2D C3D H3D1 109.9 . .
C2D C3D H3D1 109.9 . .
O2D C3D H3D2 109.9 . .
C2D C3D H3D2 109.9 . .
H3D1 C3D H3D2 108.3 . .
O2D C4D C5D 109.3(5) . .
O2D C4D H4D1 109.8 . .
C5D C4D H4D1 109.8 . .
O2D C4D H4D2 109.8 . .
C5D C4D H4D2 109.8 . .
H4D1 C4D H4D2 108.3 . .
O3D C5D C4D 110.1(5) . .
O3D C5D H5D1 109.6 . .
C4D C5D H5D1 109.6 . .
O3D C5D H5D2 109.6 . .
C4D C5D H5D2 109.6 . .
H5D1 C5D H5D2 108.2 . .
O3D C6D C1D 114.8(5) . 2_566
O3D C6D H6D1 108.6 . .
C1D C6D H6D1 108.6 2_566 .
O3D C6D H6D2 108.6 . .
C1D C6D H6D2 108.6 2_566 .
H6D1 C6D H6D2 107.5 . .
C2D O1D C1D 111.8(5) . .
C3D O2D C4D 111.3(5) . .
C6D O3D C5D 115.1(4) . .
C2S C1S C6S 117.0(6) . .
C2S C1S I1S 121.8(5) . .
C6S C1S I1S 121.2(5) . .
F1S C2S C1S 120.0(6) . .
F1S C2S C3S 118.7(7) . .
C1S C2S C3S 121.3(7) . .
F2S C3S C4S 119.2(8) . .
F2S C3S C2S 120.4(8) . .
C4S C3S C2S 120.4(8) . .
F3S C4S C5S 119.2(8) . .
F3S C4S C3S 120.5(8) . .
C5S C4S C3S 120.3(7) . .
F4S C5S C4S 120.9(7) . .
F4S C5S C6S 120.0(8) . .
C4S C5S C6S 119.0(8) . .
F5S C6S C1S 120.8(6) . .
F5S C6S C5S 117.3(7) . .
C1S C6S C5S 121.9(7) . .
C2T C1T C6T 116.8(6) . .
C2T C1T I1T 121.2(5) . .
C6T C1T I1T 121.9(5) . .
F1T C2T C1T 120.1(7) . .
F1T C2T C3T 117.4(7) . .
C1T C2T C3T 122.4(7) . .
F2T C3T C4T 120.1(8) . .
F2T C3T C2T 121.8(8) . .
C4T C3T C2T 118.1(8) . .
C5T C4T F3T 119.6(8) . .
C5T C4T C3T 121.0(7) . .
F3T C4T C3T 119.4(8) . .
F4T C5T C4T 119.6(7) . .
F4T C5T C6T 120.8(8) . .
C4T C5T C6T 119.6(8) . .
F5T C6T C1T 120.0(6) . .
F5T C6T C5T 117.9(7) . .
C1T C6T C5T 122.1(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1A N1A 1.308(6) .
C1A N2A 1.315(6) .
C1A S1A 1.718(5) .
N1A H1A1 0.8600 .
N1A H1A2 0.8600 .
N2A H2A1 0.8600 .
N2A H2A2 0.8600 .
C1C O1C 1.357(7) .
C1C C6C 1.428(9) 2_556
C1C H1C1 0.9700 .
C1C H1C2 0.9700 .
C2C O1C 1.379(7) .
C2C C3C 1.429(9) .
C2C H2C1 0.9700 .
C2C H2C2 0.9700 .
C3C O2C 1.392(7) .
C3C H3C1 0.9700 .
C3C H3C2 0.9700 .
C4C O2C 1.402(7) .
C4C C5C 1.453(8) .
C4C H4C1 0.9700 .
C4C H4C2 0.9700 .
C5C O3C 1.397(7) .
C5C H5C1 0.9700 .
C5C H5C2 0.9700 .
C6C O3C 1.390(7) .
C6C C1C 1.428(9) 2_556
C6C H6C1 0.9700 .
C6C H6C2 0.9700 .
C1C' O1C' 1.372(8) .
C1C' C6C' 1.432(9) 2_556
C1C' H1C3 0.9700 .
C1C' H1C4 0.9700 .
C2C' O1C' 1.382(8) .
C2C' C3C' 1.437(9) .
C2C' H2C3 0.9700 .
C2C' H2C4 0.9700 .
C3C' O2C' 1.384(8) .
C3C' H3C3 0.9700 .
C3C' H3C4 0.9700 .
C4C' O2C' 1.396(8) .
C4C' C5C' 1.442(9) .
C4C' H4C3 0.9700 .
C4C' H4C4 0.9700 .
C5C' O3C' 1.392(8) .
C5C' H5C3 0.9700 .
C5C' H5C4 0.9700 .
C6C' O3C' 1.378(8) .
C6C' C1C' 1.432(9) 2_556
C6C' H6C3 0.9700 .
C6C' H6C4 0.9700 .
C1D O1D 1.414(7) .
C1D C6D 1.504(9) 2_566
C1D H1D1 0.9700 .
C1D H1D2 0.9700 .
C2D O1D 1.413(7) .
C2D C3D 1.492(9) .
C2D H2D1 0.9700 .
C2D H2D2 0.9700 .
C3D O2D 1.407(7) .
C3D H3D1 0.9700 .
C3D H3D2 0.9700 .
C4D O2D 1.418(7) .
C4D C5D 1.473(8) .
C4D H4D1 0.9700 .
C4D H4D2 0.9700 .
C5D O3D 1.420(6) .
C5D H5D1 0.9700 .
C5D H5D2 0.9700 .
C6D O3D 1.404(7) .
C6D C1D 1.504(9) 2_566
C6D H6D1 0.9700 .
C6D H6D2 0.9700 .
C1S C2S 1.361(9) .
C1S C6S 1.377(9) .
C1S I1S 2.103(6) .
C2S F1S 1.324(8) .
C2S C3S 1.374(10) .
C3S F2S 1.334(9) .
C3S C4S 1.352(11) .
C4S F3S 1.345(8) .
C4S C5S 1.349(11) .
C5S F4S 1.339(9) .
C5S C6S 1.384(9) .
C6S F5S 1.342(8) .
C1T C2T 1.363(9) .
C1T C6T 1.363(9) .
C1T I1T 2.108(6) .
C2T F1T 1.331(8) .
C2T C3T 1.391(10) .
C3T F2T 1.332(9) .
C3T C4T 1.357(11) .
C4T C5T 1.348(11) .
C4T F3T 1.350(8) .
C5T F4T 1.347(8) .
C5T C6T 1.373(10) .
C6T F5T 1.337(8) .
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
_geom_torsion_site_symmetry_1
O1C C2C C3C O2C -63.6(17) .
O2C C4C C5C O3C 70.3(15) .
C6C C1C O1C C2C 175.8(13) 2_556
C3C C2C O1C C1C 176.0(12) .
C2C C3C O2C C4C 163.1(11) .
C5C C4C O2C C3C -170.6(10) .
C1C C6C O3C C5C -174.8(13) 2_556
C4C C5C O3C C6C -179.3(13) .
O1C' C2C' C3C' O2C' -56(3) .
O2C' C4C' C5C' O3C' -54(2) .
C6C' C1C' O1C' C2C' -170(3) 2_556
C3C' C2C' O1C' C1C' -165(3) .
C2C' C3C' O2C' C4C' 170.3(17) .
C5C' C4C' O2C' C3C' -76(2) .
C1C' C6C' O3C' C5C' -177(3) 2_556
C4C' C5C' O3C' C6C' -79(3) .
O1D C2D C3D O2D 64.7(7) .
O2D C4D C5D O3D 64.0(6) .
C3D C2D O1D C1D 178.7(5) .
C6D C1D O1D C2D 169.9(5) 2_566
C2D C3D O2D C4D 179.8(5) .
C5D C4D O2D C3D 173.8(5) .
C1D C6D O3D C5D 59.9(7) 2_566
C4D C5D O3D C6D 174.7(5) .
C6S C1S C2S F1S 180.0(8) .
I1S C1S C2S F1S -1.9(12) .
C6S C1S C2S C3S -1.2(13) .
I1S C1S C2S C3S 176.9(7) .
F1S C2S C3S F2S -0.9(16) .
C1S C2S C3S F2S -179.8(9) .
F1S C2S C3S C4S 178.8(9) .
C1S C2S C3S C4S -0.1(16) .
F2S C3S C4S F3S 1.6(16) .
C2S C3S C4S F3S -178.2(9) .
F2S C3S C4S C5S -178.7(10) .
C2S C3S C4S C5S 1.6(16) .
F3S C4S C5S F4S -0.5(15) .
C3S C4S C5S F4S 179.8(9) .
F3S C4S C5S C6S 178.0(8) .
C3S C4S C5S C6S -1.7(15) .
C2S C1S C6S F5S -179.1(8) .
I1S C1S C6S F5S 2.8(10) .
C2S C1S C6S C5S 1.0(12) .
I1S C1S C6S C5S -177.1(7) .
F4S C5S C6S F5S -1.0(13) .
C4S C5S C6S F5S -179.5(8) .
F4S C5S C6S C1S 178.9(8) .
C4S C5S C6S C1S 0.4(14) .
C6T C1T C2T F1T 178.9(7) .
I1T C1T C2T F1T -2.4(11) .
C6T C1T C2T C3T -0.2(12) .
I1T C1T C2T C3T 178.5(7) .
F1T C2T C3T F2T 1.4(14) .
C1T C2T C3T F2T -179.4(9) .
F1T C2T C3T C4T -179.0(9) .
C1T C2T C3T C4T 0.2(14) .
F2T C3T C4T C5T 179.3(9) .
C2T C3T C4T C5T -0.2(15) .
F2T C3T C4T F3T -1.3(15) .
C2T C3T C4T F3T 179.1(8) .
F3T C4T C5T F4T -1.1(14) .
C3T C4T C5T F4T 178.2(9) .
F3T C4T C5T C6T -179.0(8) .
C3T C4T C5T C6T 0.4(14) .
C2T C1T C6T F5T 179.9(7) .
I1T C1T C6T F5T 1.3(10) .
C2T C1T C6T C5T 0.3(12) .
I1T C1T C6T C5T -178.3(6) .
F4T C5T C6T F5T 2.1(13) .
C4T C5T C6T F5T 180.0(8) .
F4T C5T C6T C1T -178.2(8) .
C4T C5T C6T C1T -0.4(13) .
