#------------------------------------------------------------------------------
#$Date: 2022-02-01 01:09:53 +0200 (Tue, 01 Feb 2022) $
#$Revision: 272358 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/61/1566197.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_1566197
loop_
_publ_author_name
'Mirzaei, Saber'
'Espinoza Castro, Victor M.'
'Hernández Sánchez, Raúl'
_publ_section_title
;
 Nonspherical anion sequestration by C--H hydrogen bonding
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC07041J
_journal_year                    2022
_chemical_formula_moiety         '2(C H2 Cl2), C76 H72 F8 O8, C4 H6 N2'
_chemical_formula_sum            'C82 H82 Cl4 F8 N2 O8'
_chemical_formula_weight         1517.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-02-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-18 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 131.7640(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   33.1351(6)
_cell_length_b                   12.8854(2)
_cell_length_c                   23.6066(7)
_cell_measurement_reflns_used    9740
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      70.18
_cell_measurement_theta_min      3.58
_cell_volume                     7517.9(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.9-0'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      230.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            48517
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.169
_diffrn_reflns_theta_min         3.577
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.083
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0685 before and 0.0528 after correction. The Ratio of minimum to maximum transmission is 0.8832. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             3168
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.655
_refine_diff_density_min         -2.868
_refine_diff_density_rms         0.146
_refine_ls_extinction_coef       0.00015(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   2.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         7100
_refine_ls_number_restraints     80
_refine_ls_restrained_S_all      2.186
_refine_ls_R_factor_all          0.1454
_refine_ls_R_factor_gt           0.1332
_refine_ls_shift/su_max          0.444
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4235
_refine_ls_wR_factor_ref         0.4483
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5926
_reflns_number_total             7100
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc07041j2.cif
_cod_data_source_block           sm341first_a
_cod_database_code               1566197
_shelx_shelxl_version_number     2018/3
_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_max   0.903
_shelx_estimated_absorpt_t_min   0.868
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1S-C1S = N2S-C3S
 1.14 with sigma of 0.01
 C1S-C2S = C3S-C4S
 1.45 with sigma of 0.02
3. Rigid bond restraints
 C2A, F1A, C4A, F2A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C2B, F1B, C4B, F2B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
C2A \\sim F1A \\sim C4A \\sim F2A: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04
C2B \\sim F1B \\sim C4B \\sim F2B: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(C18B) \\sim Ueq, Uanis(C19B) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(Cl1S) \\sim Ueq, Uanis(Cl2S) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N1S) \\sim Ueq, Uanis(C4S) \\sim Ueq: with sigma of 0.004 and sigma for
terminal atoms of 0.015
Uanis(F1A) \\sim Ueq, Uanis(F2A) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.006
Uanis(C1A) = Uanis(C2A) = Uanis(C3A) = Uanis(C4A) = Uanis(C5A) = Uanis(C6A)
Uanis(C1B) = Uanis(C2B) = Uanis(C3B) = Uanis(C4B) = Uanis(C5B) = Uanis(C6B)
Uanis(Cl1S) = Uanis(Cl2S)
5. Others
 Fixed Sof: H2SA(0.5) H2SB(0.5) H2SC(0.5) H4SA(0.5) H4SB(0.5) H4SC(0.5)
6.a Ternary CH refined with riding coordinates:
 C14A(H14A), C14B(H14B)
6.b Secondary CH2 refined with riding coordinates:
 C5S(H5SA,H5SB), C13B(H13C,H13D), C15A(H15A,H15B), C15B(H15C,H15D), C16A(H16A,
 H16B), C16B(H16C,H16D), C17A(H17A,H17B), C17B(H17C,H17D), C18A(H18A,H18B),
 C18B(H18C,H18D)
6.c Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1B(H1B), C3A(H3A), C3B(H3B), C5A(H5A), C5B(H5B), C10A(H10A),
 C10B(H10B)
6.d Idealised Me refined as rotating group:
 C19A(H19A,H19B,H19C), C19B(H19D,H19E,H19F), C2S(H2SA,H2SB,H2SC), C4S(H4SA,
 H4SB,H4SC)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Cl1S Cl 0.2764(2) 0.7248(5) 0.3492(3) 0.2175(17) Uani 1 1 d . U . . .
Cl2S Cl 0.2157(2) 0.5379(6) 0.3326(3) 0.2175(17) Uani 1 1 d . U . . .
C5S C 0.2276(3) 0.6834(6) 0.3317(5) 0.093(2) Uani 1 1 d . . . . .
H5SA H 0.196538 0.708925 0.280946 0.112 Uiso 1 1 calc R . . . .
H5SB H 0.225733 0.716572 0.367202 0.112 Uiso 1 1 calc R . . . .
F1A F 0.3594(2) 0.7894(3) 0.1998(3) 0.1039(16) Uani 1 1 d . U . . .
F1B F 0.55492(18) 0.7913(2) 0.4636(3) 0.0951(15) Uani 1 1 d . U . . .
F2A F 0.2301(2) 0.6180(4) 0.1908(3) 0.1103(17) Uani 1 1 d . U . . .
F2B F 0.70273(17) 0.6389(3) 0.69215(19) 0.0794(12) Uani 1 1 d . U . . .
O1A O 0.41100(11) 0.4128(2) 0.34372(15) 0.0330(7) Uani 1 1 d . . . . .
O1B O 0.67010(11) 0.4109(2) 0.49970(15) 0.0350(7) Uani 1 1 d . . . . .
O2A O 0.30793(11) 0.4118(2) 0.07663(15) 0.0336(7) Uani 1 1 d . . . . .
O2B O 0.50486(11) 0.4213(2) 0.44999(15) 0.0338(7) Uani 1 1 d . . . . .
C1A C 0.3596(3) 0.6083(4) 0.2034(3) 0.0610(7) Uani 1 1 d . . . . .
H1A H 0.388682 0.605373 0.205016 0.073 Uiso 1 1 calc R . . . .
C1B C 0.5699(2) 0.6121(3) 0.4662(3) 0.0471(6) Uani 1 1 d . . . . .
H1B H 0.539067 0.607162 0.414212 0.057 Uiso 1 1 calc R . . . .
C2A C 0.3386(3) 0.7023(4) 0.1998(3) 0.0610(7) Uani 1 1 d . U . . .
C2B C 0.5850(2) 0.7065(3) 0.5028(3) 0.0471(6) Uani 1 1 d . U . . .
C3A C 0.2936(3) 0.7091(4) 0.1949(3) 0.0610(7) Uani 1 1 d . . . . .
H3A H 0.278560 0.773237 0.191501 0.073 Uiso 1 1 calc R . . . .
C3B C 0.6296(2) 0.7188(3) 0.5792(3) 0.0471(6) Uani 1 1 d . . . . .
H3B H 0.639182 0.783529 0.603604 0.057 Uiso 1 1 calc R . . . .
C4A C 0.2734(3) 0.6170(4) 0.1954(3) 0.0610(7) Uani 1 1 d . U . . .
C4B C 0.6591(2) 0.6298(3) 0.6174(3) 0.0471(6) Uani 1 1 d . U . . .
C5A C 0.2943(3) 0.5222(4) 0.1996(3) 0.0610(7) Uani 1 1 d . . . . .
H5A H 0.278744 0.460688 0.198918 0.073 Uiso 1 1 calc R . . . .
C5B C 0.6455(2) 0.5342(3) 0.5834(3) 0.0471(6) Uani 1 1 d . . . . .
H5B H 0.666517 0.475542 0.611785 0.057 Uiso 1 1 calc R . . . .
C6A C 0.3378(3) 0.5176(4) 0.2046(3) 0.0610(7) Uani 1 1 d . . . . .
C6B C 0.6003(2) 0.5249(3) 0.5065(3) 0.0471(6) Uani 1 1 d . . . . .
C7A C 0.36192(15) 0.4150(3) 0.2109(2) 0.0308(8) Uani 1 1 d . . . . .
C7B C 0.58529(16) 0.4213(3) 0.4688(2) 0.0317(8) Uani 1 1 d . . . . .
C8A C 0.39982(15) 0.3658(3) 0.2817(2) 0.0303(8) Uani 1 1 d . . . . .
C8B C 0.61973(15) 0.3693(3) 0.4637(2) 0.0299(8) Uani 1 1 d . . . . .
C9A C 0.42368(15) 0.2715(3) 0.2898(2) 0.0291(8) Uani 1 1 d . . . . .
C9B C 0.60581(15) 0.2729(3) 0.4269(2) 0.0287(8) Uani 1 1 d . . . . .
C10A C 0.40865(15) 0.2256(3) 0.2244(2) 0.0297(8) Uani 1 1 d . . . . .
H10A H 0.424392 0.161927 0.228950 0.036 Uiso 1 1 calc R . . . .
C10B C 0.55616(15) 0.2302(3) 0.39597(19) 0.0292(8) Uani 1 1 d . . . . .
H10B H 0.545730 0.166559 0.370058 0.035 Uiso 1 1 calc R . . . .
C11A C 0.37089(14) 0.2713(3) 0.15225(19) 0.0280(8) Uani 1 1 d . . . . .
C11B C 0.52159(15) 0.2775(3) 0.40191(19) 0.0289(8) Uani 1 1 d . . . . .
C12A C 0.34847(15) 0.3656(3) 0.1471(2) 0.0306(8) Uani 1 1 d . . . . .
C12B C 0.53575(15) 0.3743(3) 0.4370(2) 0.0299(8) Uani 1 1 d . . . . .
C13A C 0.32476(18) 0.4713(3) 0.0456(2) 0.0351(9) Uani 1 1 d . . . . .
C13B C 0.45810(16) 0.4766(3) 0.3895(2) 0.0349(8) Uani 1 1 d . . . . .
H13C H 0.464193 0.506596 0.357593 0.042 Uiso 1 1 calc R . . . .
H13D H 0.451972 0.533879 0.410326 0.042 Uiso 1 1 calc R . . . .
C14A C 0.35695(15) 0.2231(3) 0.0821(2) 0.0303(8) Uani 1 1 d . . . . .
H14A H 0.319572 0.244759 0.037828 0.036 Uiso 1 1 calc R . . . .
C14B C 0.46803(15) 0.2281(3) 0.3698(2) 0.0287(8) Uani 1 1 d . . . . .
H14B H 0.460173 0.252948 0.401228 0.034 Uiso 1 1 calc R . . . .
C15A C 0.35772(16) 0.1037(3) 0.0829(2) 0.0321(8) Uani 1 1 d . . . . .
H15A H 0.394920 0.079577 0.123430 0.038 Uiso 1 1 calc R . . . .
H15B H 0.335779 0.078220 0.094037 0.038 Uiso 1 1 calc R . . . .
C15B C 0.47069(17) 0.1088(3) 0.3751(2) 0.0344(8) Uani 1 1 d . . . . .
H15C H 0.468423 0.080753 0.334468 0.041 Uiso 1 1 calc R . . . .
H15D H 0.505725 0.088192 0.423719 0.041 Uiso 1 1 calc R . . . .
C16A C 0.33595(19) 0.0584(3) 0.0073(2) 0.0408(9) Uani 1 1 d . . . . .
H16A H 0.354299 0.091732 -0.007493 0.049 Uiso 1 1 calc R . . . .
H16B H 0.297248 0.074009 -0.031834 0.049 Uiso 1 1 calc R . . . .
C16B C 0.4262(2) 0.0621(4) 0.3689(3) 0.0478(11) Uani 1 1 d . . . . .
H16C H 0.391183 0.078590 0.318863 0.057 Uiso 1 1 calc R . . . .
H16D H 0.426941 0.093307 0.407406 0.057 Uiso 1 1 calc R . . . .
C17A C 0.3440(2) -0.0591(3) 0.0110(3) 0.0475(10) Uani 1 1 d . . . . .
H17A H 0.335054 -0.081793 -0.035893 0.057 Uiso 1 1 calc R . . . .
H17B H 0.382329 -0.074824 0.053346 0.057 Uiso 1 1 calc R . . . .
C17B C 0.4316(3) -0.0571(4) 0.3796(3) 0.0610(14) Uani 1 1 d . . . . .
H17C H 0.427726 -0.088180 0.338266 0.073 Uiso 1 1 calc R . . . .
H17D H 0.468067 -0.073292 0.427349 0.073 Uiso 1 1 calc R . . . .
C18A C 0.3101(3) -0.1204(4) 0.0211(4) 0.0574(13) Uani 1 1 d . . . . .
H18A H 0.271802 -0.105546 -0.021471 0.069 Uiso 1 1 calc R . . . .
H18B H 0.318899 -0.097650 0.067849 0.069 Uiso 1 1 calc R . . . .
C18B C 0.3912(3) -0.1061(5) 0.3808(5) 0.0823(18) Uani 1 1 d . U . . .
H18C H 0.354796 -0.095530 0.331374 0.099 Uiso 1 1 calc R . . . .
H18D H 0.392920 -0.071448 0.419308 0.099 Uiso 1 1 calc R . . . .
C19A C 0.3195(3) -0.2382(4) 0.0253(4) 0.0687(16) Uani 1 1 d . . . . .
H19A H 0.303585 -0.263768 -0.024384 0.103 Uiso 1 1 calc GR . . . .
H19B H 0.302653 -0.272603 0.041664 0.103 Uiso 1 1 calc GR . . . .
H19C H 0.357993 -0.252420 0.061400 0.103 Uiso 1 1 calc GR . . . .
C19B C 0.4007(4) -0.2204(6) 0.3978(5) 0.098(2) Uani 1 1 d . U . . .
H19D H 0.366159 -0.255962 0.367918 0.147 Uiso 1 1 calc GR . . . .
H19E H 0.420900 -0.231598 0.451359 0.147 Uiso 1 1 calc GR . . . .
H19F H 0.421074 -0.247418 0.384980 0.147 Uiso 1 1 calc GR . . . .
N1S N 0.500000 0.6105(9) 0.250000 0.211(9) Uani 1 2 d DS TU P . .
C1S C 0.500000 0.5229(7) 0.250000 0.093(3) Uani 1 2 d DS T P . .
C2S C 0.500000 0.4166(5) 0.250000 0.0488(15) Uani 1 2 d DS T P . .
H2SA H 0.464900 0.391505 0.204922 0.073 Uiso 0.5 1 calc GR . . A -1
H2SB H 0.507407 0.391505 0.294881 0.073 Uiso 0.5 1 calc GR . . A -1
H2SC H 0.527693 0.391505 0.250197 0.073 Uiso 0.5 1 calc GR . . A -1
N2S N 0.500000 0.0302(5) 0.250000 0.0706(18) Uani 1 2 d DS T P . .
C3S C 0.500000 -0.0558(5) 0.250000 0.079(3) Uani 1 2 d DS T P . .
C4S C 0.500000 -0.1702(13) 0.250000 0.208(11) Uani 1 2 d DS TU P . .
H4SA H 0.467885 -0.195255 0.239219 0.313 Uiso 0.5 1 calc GR . . B -1
H4SB H 0.531975 -0.195255 0.299390 0.313 Uiso 0.5 1 calc GR . . B -1
H4SC H 0.500140 -0.195255 0.211391 0.313 Uiso 0.5 1 calc GR . . B -1
H13A H 0.298(2) 0.509(4) 0.016(3) 0.034(11) Uiso 1 1 d . . . . .
H13B H 0.358(2) 0.496(4) 0.082(3) 0.035(11) Uiso 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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
Cl1S C5S Cl2S 123.0(5) . . ?
Cl1S C5S H5SA 106.6 . . ?
Cl1S C5S H5SB 106.6 . . ?
Cl2S C5S H5SA 106.6 . . ?
Cl2S C5S H5SB 106.6 . . ?
H5SA C5S H5SB 106.5 . . ?
C8A O1A C13B 116.1(3) . . ?
C8B O1B C13A 116.8(3) . 2_655 ?
C12A O2A C13A 116.9(3) . . ?
C12B O2B C13B 118.0(3) . . ?
C2A C1A H1A 120.1 . . ?
C2A C1A C6A 119.8(6) . . ?
C6A C1A H1A 120.1 . . ?
C2B C1B H1B 120.2 . . ?
C2B C1B C6B 119.5(5) . . ?
C6B C1B H1B 120.2 . . ?
F1A C2A C1A 120.6(6) . . ?
F1A C2A C3A 118.0(5) . . ?
C1A C2A C3A 121.4(6) . . ?
F1B C2B C1B 119.4(5) . . ?
F1B C2B C3B 117.5(4) . . ?
C1B C2B C3B 123.1(5) . . ?
C2A C3A H3A 121.9 . . ?
C4A C3A C2A 116.1(5) . . ?
C4A C3A H3A 121.9 . . ?
C2B C3B H3B 122.2 . . ?
C4B C3B C2B 115.6(4) . . ?
C4B C3B H3B 122.2 . . ?
F2A C4A C3A 119.1(5) . . ?
F2A C4A C5A 117.9(6) . . ?
C3A C4A C5A 123.0(6) . . ?
F2B C4B C3B 117.2(4) . . ?
F2B C4B C5B 119.5(5) . . ?
C5B C4B C3B 123.3(5) . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A C4A 119.8(6) . . ?
C6A C5A H5A 120.1 . . ?
C4B C5B H5B 120.3 . . ?
C4B C5B C6B 119.3(5) . . ?
C6B C5B H5B 120.3 . . ?
C1A C6A C7A 119.6(5) . . ?
C5A C6A C1A 119.8(5) . . ?
C5A C6A C7A 120.6(5) . . ?
C1B C6B C5B 119.2(4) . . ?
C1B C6B C7B 121.1(4) . . ?
C5B C6B C7B 119.7(4) . . ?
C8A C7A C6A 120.7(3) . . ?
C8A C7A C12A 117.7(3) . . ?
C12A C7A C6A 121.6(4) . . ?
C8B C7B C6B 120.9(4) . . ?
C8B C7B C12B 118.5(3) . . ?
C12B C7B C6B 120.5(3) . . ?
O1A C8A C7A 117.2(3) . . ?
O1A C8A C9A 120.6(3) . . ?
C9A C8A C7A 122.2(3) . . ?
O1B C8B C7B 118.9(3) . . ?
O1B C8B C9B 119.1(3) . . ?
C7B C8B C9B 121.8(3) . . ?
C8A C9A C10A 117.7(3) . . ?
C8A C9A C14B 118.7(3) . . ?
C10A C9A C14B 123.4(3) . . ?
C8B C9B C14A 119.7(3) . 2_655 ?
C10B C9B C8B 117.3(3) . . ?
C10B C9B C14A 122.9(3) . 2_655 ?
C9A C10A H10A 118.8 . . ?
C9A C10A C11A 122.5(3) . . ?
C11A C10A H10A 118.8 . . ?
C9B C10B H10B 118.6 . . ?
C11B C10B C9B 122.7(3) . . ?
C11B C10B H10B 118.6 . . ?
C10A C11A C14A 121.9(3) . . ?
C12A C11A C10A 117.7(3) . . ?
C12A C11A C14A 120.3(3) . . ?
C10B C11B C12B 118.7(3) . . ?
C10B C11B C14B 122.1(3) . . ?
C12B C11B C14B 119.2(3) . . ?
O2A C12A C7A 116.8(3) . . ?
C11A C12A O2A 120.8(3) . . ?
C11A C12A C7A 122.2(3) . . ?
O2B C12B C7B 117.7(3) . . ?
O2B C12B C11B 121.0(3) . . ?
C11B C12B C7B 120.9(3) . . ?
O1B C13A H13A 107(3) 2_655 . ?
O1B C13A H13B 104(3) 2_655 . ?
O2A C13A O1B 112.3(3) . 2_655 ?
O2A C13A H13A 100(3) . . ?
O2A C13A H13B 110(3) . . ?
H13A C13A H13B 123(4) . . ?
O1A C13B H13C 109.1 . . ?
O1A C13B H13D 109.1 . . ?
O2B C13B O1A 112.6(3) . . ?
O2B C13B H13C 109.1 . . ?
O2B C13B H13D 109.1 . . ?
H13C C13B H13D 107.8 . . ?
C9B C14A H14A 107.1 2_655 . ?
C9B C14A C15A 114.5(3) 2_655 . ?
C11A C14A C9B 107.0(3) . 2_655 ?
C11A C14A H14A 107.1 . . ?
C11A C14A C15A 113.8(3) . . ?
C15A C14A H14A 107.1 . . ?
C9A C14B H14B 106.9 . . ?
C9A C14B C15B 114.9(3) . . ?
C11B C14B C9A 107.7(3) . . ?
C11B C14B H14B 106.9 . . ?
C11B C14B C15B 113.0(3) . . ?
C15B C14B H14B 106.9 . . ?
C14A C15A H15A 109.2 . . ?
C14A C15A H15B 109.2 . . ?
H15A C15A H15B 107.9 . . ?
C16A C15A C14A 112.2(3) . . ?
C16A C15A H15A 109.2 . . ?
C16A C15A H15B 109.2 . . ?
C14B C15B H15C 109.0 . . ?
C14B C15B H15D 109.0 . . ?
H15C C15B H15D 107.8 . . ?
C16B C15B C14B 113.1(3) . . ?
C16B C15B H15C 109.0 . . ?
C16B C15B H15D 109.0 . . ?
C15A C16A H16A 109.1 . . ?
C15A C16A H16B 109.1 . . ?
C15A C16A C17A 112.6(3) . . ?
H16A C16A H16B 107.8 . . ?
C17A C16A H16A 109.1 . . ?
C17A C16A H16B 109.1 . . ?
C15B C16B H16C 109.1 . . ?
C15B C16B H16D 109.1 . . ?
C15B C16B C17B 112.4(4) . . ?
H16C C16B H16D 107.9 . . ?
C17B C16B H16C 109.1 . . ?
C17B C16B H16D 109.1 . . ?
C16A C17A H17A 108.8 . . ?
C16A C17A H17B 108.8 . . ?
H17A C17A H17B 107.7 . . ?
C18A C17A C16A 113.8(4) . . ?
C18A C17A H17A 108.8 . . ?
C18A C17A H17B 108.8 . . ?
C16B C17B H17C 108.7 . . ?
C16B C17B H17D 108.6 . . ?
H17C C17B H17D 107.6 . . ?
C18B C17B C16B 114.4(5) . . ?
C18B C17B H17C 108.7 . . ?
C18B C17B H17D 108.6 . . ?
C17A C18A H18A 109.0 . . ?
C17A C18A H18B 109.0 . . ?
C17A C18A C19A 112.7(4) . . ?
H18A C18A H18B 107.8 . . ?
C19A C18A H18A 109.0 . . ?
C19A C18A H18B 109.0 . . ?
C17B C18B H18C 109.0 . . ?
C17B C18B H18D 109.0 . . ?
C17B C18B C19B 112.8(7) . . ?
H18C C18B H18D 107.8 . . ?
C19B C18B H18C 109.0 . . ?
C19B C18B H18D 109.0 . . ?
C18A C19A H19A 109.5 . . ?
C18A C19A H19B 109.5 . . ?
C18A C19A H19C 109.5 . . ?
H19A C19A H19B 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C18B C19B H19D 109.5 . . ?
C18B C19B H19E 109.5 . . ?
C18B C19B H19F 109.5 . . ?
H19D C19B H19E 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
N1S C1S C2S 180.0 . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
N2S C3S C4S 180.0 . . ?
C3S C4S H4SA 120.0 . . ?
C3S C4S H4SB 120.0 . . ?
C3S C4S H4SC 120.0 . . ?
H4SA C4S H4SB 97.1 . . ?
H4SA C4S H4SC 97.1 . . ?
H4SB C4S H4SC 97.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1S C5S 1.476(11) . ?
Cl2S C5S 1.919(11) . ?
C5S H5SA 0.9800 . ?
C5S H5SB 0.9800 . ?
F1A C2A 1.316(8) . ?
F1B C2B 1.348(6) . ?
F2A C4A 1.364(8) . ?
F2B C4B 1.348(6) . ?
O1A C8A 1.388(4) . ?
O1A C13B 1.426(5) . ?
O1B C8B 1.380(4) . ?
O1B C13A 1.421(5) 2_655 ?
O2A C12A 1.395(4) . ?
O2A C13A 1.408(5) . ?
O2B C12B 1.389(4) . ?
O2B C13B 1.414(5) . ?
C1A H1A 0.9400 . ?
C1A C2A 1.371(7) . ?
C1A C6A 1.384(8) . ?
C1B H1B 0.9400 . ?
C1B C2B 1.378(6) . ?
C1B C6B 1.380(7) . ?
C2A C3A 1.420(9) . ?
C2B C3B 1.383(7) . ?
C3A H3A 0.9400 . ?
C3A C4A 1.367(9) . ?
C3B H3B 0.9400 . ?
C3B C4B 1.382(7) . ?
C4A C5A 1.377(7) . ?
C4B C5B 1.373(6) . ?
C5A H5A 0.9400 . ?
C5A C6A 1.364(9) . ?
C5B H5B 0.9400 . ?
C5B C6B 1.390(7) . ?
C6A C7A 1.501(6) . ?
C6B C7B 1.494(5) . ?
C7A C8A 1.406(5) . ?
C7A C12A 1.407(5) . ?
C7B C8B 1.395(5) . ?
C7B C12B 1.408(5) . ?
C8A C9A 1.392(5) . ?
C8B C9B 1.406(5) . ?
C9A C10A 1.397(5) . ?
C9A C14B 1.530(5) . ?
C9B C10B 1.394(5) . ?
C9B C14A 1.526(5) 2_655 ?
C10A H10A 0.9400 . ?
C10A C11A 1.405(5) . ?
C10B H10B 0.9400 . ?
C10B C11B 1.385(5) . ?
C11A C12A 1.387(5) . ?
C11A C14A 1.523(5) . ?
C11B C12B 1.394(5) . ?
C11B C14B 1.529(5) . ?
C13A H13A 0.82(5) . ?
C13A H13B 0.88(5) . ?
C13B H13C 0.9800 . ?
C13B H13D 0.9800 . ?
C14A H14A 0.9900 . ?
C14A C15A 1.539(5) . ?
C14B H14B 0.9900 . ?
C14B C15B 1.540(5) . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A C16A 1.526(5) . ?
C15B H15C 0.9800 . ?
C15B H15D 0.9800 . ?
C15B C16B 1.506(6) . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A C17A 1.529(6) . ?
C16B H16C 0.9800 . ?
C16B H16D 0.9800 . ?
C16B C17B 1.547(6) . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A C18A 1.517(7) . ?
C17B H17C 0.9800 . ?
C17B H17D 0.9800 . ?
C17B C18B 1.498(9) . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A C19A 1.538(7) . ?
C18B H18C 0.9800 . ?
C18B H18D 0.9800 . ?
C18B C19B 1.504(10) . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C19A H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C19B H19E 0.9700 . ?
C19B H19F 0.9700 . ?
N1S C1S 1.128(9) . ?
C1S C2S 1.370(10) . ?
C2S H2SA 0.9700 . ?
C2S H2SB 0.9700 . ?
C2S H2SC 0.9700 . ?
N2S C3S 1.109(7) . ?
C3S C4S 1.473(16) . ?
C4S H4SA 1.0726 . ?
C4S H4SB 1.0726 . ?
C4S H4SC 1.0726 . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1A C2A C3A C4A -179.8(5) . . . . ?
F1B C2B C3B C4B 179.5(4) . . . . ?
F2A C4A C5A C6A -179.7(5) . . . . ?
F2B C4B C5B C6B 179.6(4) . . . . ?
O1A C8A C9A C10A 176.9(3) . . . . ?
O1A C8A C9A C14B -8.1(5) . . . . ?
O1B C8B C9B C10B 175.5(3) . . . . ?
O1B C8B C9B C14A -8.2(5) . . . 2_655 ?
C1A C2A C3A C4A 1.2(8) . . . . ?
C1A C6A C7A C8A 96.8(5) . . . . ?
C1A C6A C7A C12A -82.0(6) . . . . ?
C1B C2B C3B C4B 0.9(7) . . . . ?
C1B C6B C7B C8B 116.6(5) . . . . ?
C1B C6B C7B C12B -62.9(5) . . . . ?
C2A C1A C6A C5A 2.3(8) . . . . ?
C2A C1A C6A C7A -178.2(4) . . . . ?
C2A C3A C4A F2A -179.9(5) . . . . ?
C2A C3A C4A C5A -0.7(8) . . . . ?
C2B C1B C6B C5B 0.3(6) . . . . ?
C2B C1B C6B C7B -179.7(4) . . . . ?
C2B C3B C4B F2B -179.9(4) . . . . ?
C2B C3B C4B C5B -0.9(7) . . . . ?
C3A C4A C5A C6A 1.1(8) . . . . ?
C3B C4B C5B C6B 0.7(7) . . . . ?
C4A C5A C6A C1A -1.8(8) . . . . ?
C4A C5A C6A C7A 178.6(4) . . . . ?
C4B C5B C6B C1B -0.4(6) . . . . ?
C4B C5B C6B C7B 179.6(4) . . . . ?
C5A C6A C7A C8A -83.7(6) . . . . ?
C5A C6A C7A C12A 97.5(5) . . . . ?
C5B C6B C7B C8B -63.4(5) . . . . ?
C5B C6B C7B C12B 117.1(4) . . . . ?
C6A C1A C2A F1A 179.0(5) . . . . ?
C6A C1A C2A C3A -2.0(8) . . . . ?
C6A C7A C8A O1A 3.9(5) . . . . ?
C6A C7A C8A C9A -178.9(4) . . . . ?
C6A C7A C12A O2A -5.7(6) . . . . ?
C6A C7A C12A C11A 179.4(4) . . . . ?
C6B C1B C2B F1B -179.2(4) . . . . ?
C6B C1B C2B C3B -0.6(7) . . . . ?
C6B C7B C8B O1B 5.3(5) . . . . ?
C6B C7B C8B C9B -178.4(4) . . . . ?
C6B C7B C12B O2B -7.6(5) . . . . ?
C6B C7B C12B C11B -179.8(3) . . . . ?
C7A C8A C9A C10A -0.2(5) . . . . ?
C7A C8A C9A C14B 174.8(3) . . . . ?
C7B C8B C9B C10B -0.7(5) . . . . ?
C7B C8B C9B C14A 175.6(3) . . . 2_655 ?
C8A O1A C13B O2B -91.3(4) . . . . ?
C8A C7A C12A O2A 175.4(3) . . . . ?
C8A C7A C12A C11A 0.6(5) . . . . ?
C8A C9A C10A C11A 0.0(5) . . . . ?
C8A C9A C14B C11B -84.8(4) . . . . ?
C8A C9A C14B C15B 148.3(3) . . . . ?
C8B C7B C12B O2B 172.8(3) . . . . ?
C8B C7B C12B C11B 0.7(5) . . . . ?
C8B C9B C10B C11B -1.5(5) . . . . ?
C9A C10A C11A C12A 0.4(5) . . . . ?
C9A C10A C11A C14A 177.0(3) . . . . ?
C9A C14B C15B C16B -75.2(4) . . . . ?
C9B C10B C11B C12B 3.2(5) . . . . ?
C9B C10B C11B C14B -178.2(3) . . . . ?
C9B C14A C15A C16A -64.6(4) 2_655 . . . ?
C10A C9A C14B C11B 89.9(4) . . . . ?
C10A C9A C14B C15B -37.0(5) . . . . ?
C10A C11A C12A O2A -175.4(3) . . . . ?
C10A C11A C12A C7A -0.7(5) . . . . ?
C10A C11A C14A C9B -92.9(4) . . . 2_655 ?
C10A C11A C14A C15A 34.5(5) . . . . ?
C10B C11B C12B O2B -174.7(3) . . . . ?
C10B C11B C12B C7B -2.8(5) . . . . ?
C10B C11B C14B C9A -93.8(4) . . . . ?
C10B C11B C14B C15B 34.2(4) . . . . ?
C11A C14A C15A C16A 171.9(3) . . . . ?
C11B C14B C15B C16B 160.6(3) . . . . ?
C12A O2A C13A O1B 89.2(4) . . . 2_655 ?
C12A C7A C8A O1A -177.2(3) . . . . ?
C12A C7A C8A C9A -0.1(5) . . . . ?
C12A C11A C14A C9B 83.5(4) . . . 2_655 ?
C12A C11A C14A C15A -149.1(3) . . . . ?
C12B O2B C13B O1A 89.7(4) . . . . ?
C12B C7B C8B O1B -175.1(3) . . . . ?
C12B C7B C8B C9B 1.1(5) . . . . ?
C12B C11B C14B C9A 84.8(4) . . . . ?
C12B C11B C14B C15B -147.2(3) . . . . ?
C13A O1B C8B C7B -97.1(4) 2_655 . . . ?
C13A O1B C8B C9B 86.5(4) 2_655 . . . ?
C13A O2A C12A C7A 101.2(4) . . . . ?
C13A O2A C12A C11A -83.8(4) . . . . ?
C13B O1A C8A C7A -97.2(4) . . . . ?
C13B O1A C8A C9A 85.6(4) . . . . ?
C13B O2B C12B C7B 105.4(4) . . . . ?
C13B O2B C12B C11B -82.4(4) . . . . ?
C14A C9B C10B C11B -177.6(3) 2_655 . . . ?
C14A C11A C12A O2A 8.0(5) . . . . ?
C14A C11A C12A C7A -177.3(3) . . . . ?
C14A C15A C16A C17A 171.7(4) . . . . ?
C14B C9A C10A C11A -174.7(3) . . . . ?
C14B C11B C12B O2B 6.7(5) . . . . ?
C14B C11B C12B C7B 178.6(3) . . . . ?
C14B C15B C16B C17B -176.3(4) . . . . ?
C15A C16A C17A C18A 68.0(5) . . . . ?
C15B C16B C17B C18B 174.8(5) . . . . ?
C16A C17A C18A C19A -179.5(5) . . . . ?
C16B C17B C18B C19B -175.2(6) . . . . ?
