#------------------------------------------------------------------------------
#$Date: 2025-04-22 19:48:50 +0300 (Tue, 22 Apr 2025) $
#$Revision: 299347 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/59/8105933.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_8105933
loop_
_publ_author_name
'Sun, Yue'
'Wang, Shu-Xia'
'Hou, Gui-Ge'
_publ_section_title
;
 Crystal structure of
 (3E,5E)-3,5-bis(3-nitrobenzylidene)-1-((4-(trifluoromethyl)phenyl)sulfonyl)piperidin-4-one
 --- dichloromethane (2/1), C53H38Cl2F6N6O14S2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1047
_journal_page_last               1049
_journal_paper_doi               10.1515/ncrs-2019-0253
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C26 H18 F3 N3 O7 S, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C26.5 H19 Cl F3 N3 O7 S'
_chemical_formula_weight         615.95
_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
_cell_angle_alpha                69.365(5)
_cell_angle_beta                 76.620(5)
_cell_angle_gamma                77.292(4)
_cell_formula_units_Z            4
_cell_length_a                   12.1975(6)
_cell_length_b                   13.9973(7)
_cell_length_c                   16.3818(10)
_cell_measurement_reflns_used    12067
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      28.9730
_cell_measurement_theta_min      2.1670
_cell_volume                     2516.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2017/1 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.02(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'CCD plate'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            32642
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.637
_diffrn_reflns_theta_min         2.011
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_description       block
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.840
_refine_diff_density_min         -1.023
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     748
_refine_ls_number_reflns         12083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0566P)²+3.0978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1413
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9426
_reflns_number_total             12083
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0253_suppl.cif
_cod_data_source_block           H22a
_cod_depositor_comments
;

2025-04-22
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C53 H38 Cl2 F6 N6 O14 S2'
_cod_original_formula_weight         1231.91
_cod_original_formula_moiety         '2(C26 H18 F3 N3 O7 S), C H2 Cl2'
_cod_original_formula_units_Z            2
_cod_database_code               8105933
_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   0.960
_shelx_estimated_absorpt_t_max   0.972
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
C1 C 0.8280(2) 0.59233(17) 0.62487(15) 0.0155(5) Uani 1 1 d . . . . .
H1A H 0.903306 0.553515 0.614371 0.019 Uiso 1 1 calc R U . . .
H1B H 0.771714 0.547615 0.637103 0.019 Uiso 1 1 calc R U . . .
C2 C 0.81726(19) 0.63143(17) 0.70176(15) 0.0144(4) Uani 1 1 d . . . . .
C3 C 0.7305(2) 0.72551(17) 0.70534(15) 0.0153(5) Uani 1 1 d . . . . .
C4 C 0.65484(19) 0.76653(17) 0.63694(15) 0.0145(5) Uani 1 1 d . . . . .
C5 C 0.68973(19) 0.73525(17) 0.55463(15) 0.0140(4) Uani 1 1 d . . . . .
H5A H 0.640507 0.688521 0.556361 0.017 Uiso 1 1 calc R U . . .
H5B H 0.680813 0.795930 0.503175 0.017 Uiso 1 1 calc R U . . .
C6 C 0.88242(19) 0.59230(17) 0.76486(15) 0.0143(4) Uani 1 1 d . . . . .
H6 H 0.870004 0.627684 0.805534 0.017 Uiso 1 1 calc R U . . .
C7 C 0.9708(2) 0.50104(17) 0.77835(15) 0.0149(5) Uani 1 1 d . . . . .
C8 C 1.0674(2) 0.50570(19) 0.80817(15) 0.0172(5) Uani 1 1 d . . . . .
H8 H 1.074939 0.565246 0.818064 0.021 Uiso 1 1 calc R U . . .
C9 C 1.1517(2) 0.42030(19) 0.82273(15) 0.0188(5) Uani 1 1 d . . . . .
C10 C 1.1425(2) 0.32790(19) 0.81352(16) 0.0209(5) Uani 1 1 d . . . . .
H10 H 1.199264 0.270953 0.826024 0.025 Uiso 1 1 calc R U . . .
C11 C 1.0455(2) 0.32291(18) 0.78498(15) 0.0183(5) Uani 1 1 d . . . . .
H11 H 1.036940 0.261847 0.778232 0.022 Uiso 1 1 calc R U . . .
C12 C 0.9616(2) 0.40866(18) 0.76653(15) 0.0164(5) Uani 1 1 d . . . . .
H12 H 0.898171 0.404876 0.745999 0.020 Uiso 1 1 calc R U . . .
C13 C 0.5572(2) 0.82874(17) 0.65510(16) 0.0162(5) Uani 1 1 d . . . . .
H13 H 0.547154 0.841296 0.708656 0.019 Uiso 1 1 calc R U . . .
C14 C 0.46498(19) 0.87946(17) 0.60396(15) 0.0154(5) Uani 1 1 d . . . . .
C15 C 0.45007(19) 0.85943(17) 0.52943(16) 0.0164(5) Uani 1 1 d . . . . .
H15 H 0.501062 0.809941 0.508405 0.020 Uiso 1 1 calc R U . . .
C16 C 0.3589(2) 0.91410(18) 0.48789(16) 0.0183(5) Uani 1 1 d . . . . .
C17 C 0.2794(2) 0.98875(18) 0.51577(17) 0.0208(5) Uani 1 1 d . . . . .
H17 H 0.220000 1.025684 0.485074 0.025 Uiso 1 1 calc R U . . .
C18 C 0.2918(2) 1.00611(18) 0.59105(17) 0.0198(5) Uani 1 1 d . . . . .
H18 H 0.238796 1.054039 0.612694 0.024 Uiso 1 1 calc R U . . .
C19 C 0.3826(2) 0.95265(18) 0.63425(17) 0.0183(5) Uani 1 1 d . . . . .
H19 H 0.389460 0.965427 0.684717 0.022 Uiso 1 1 calc R U . . .
C20 C 0.77964(19) 0.61476(17) 0.41905(15) 0.0138(4) Uani 1 1 d . . . . .
C21 C 0.7972(2) 0.50770(18) 0.44643(16) 0.0170(5) Uani 1 1 d . . . . .
H21 H 0.857179 0.470219 0.476209 0.020 Uiso 1 1 calc R U . . .
C22 C 0.7238(2) 0.45745(18) 0.42871(16) 0.0190(5) Uani 1 1 d . . . . .
H22 H 0.733721 0.385674 0.447072 0.023 Uiso 1 1 calc R U . . .
C23 C 0.6354(2) 0.51491(18) 0.38337(16) 0.0172(5) Uani 1 1 d . . . . .
C24 C 0.6180(2) 0.62231(19) 0.35600(16) 0.0173(5) Uani 1 1 d . . . . .
H24 H 0.558055 0.659757 0.326090 0.021 Uiso 1 1 calc R U . . .
C25 C 0.6908(2) 0.67280(18) 0.37381(15) 0.0157(5) Uani 1 1 d . . . . .
H25 H 0.680585 0.744577 0.355818 0.019 Uiso 1 1 calc R U . . .
C26 C 0.5533(2) 0.4599(2) 0.36834(17) 0.0212(5) Uani 1 1 d . . . . .
C27 C 1.03724(19) 0.10536(17) 0.02346(16) 0.0157(5) Uani 1 1 d . . . . .
H27A H 1.055584 0.114441 -0.039419 0.019 Uiso 1 1 calc R U . . .
H27B H 1.071374 0.036332 0.054594 0.019 Uiso 1 1 calc R U . . .
C28 C 1.08701(19) 0.18383(17) 0.04234(15) 0.0142(4) Uani 1 1 d . . . . .
C29 C 1.0148(2) 0.28708(17) 0.03753(15) 0.0154(5) Uani 1 1 d . . . . .
C30 C 0.90077(19) 0.30703(17) 0.00905(15) 0.0138(4) Uani 1 1 d . . . . .
C31 C 0.8543(2) 0.21691(17) 0.00460(16) 0.0161(5) Uani 1 1 d . . . . .
H31A H 0.773954 0.221683 0.030108 0.019 Uiso 1 1 calc R U . . .
H31B H 0.860914 0.222279 -0.056965 0.019 Uiso 1 1 calc R U . . .
C32 C 1.1905(2) 0.16554(18) 0.06454(15) 0.0163(5) Uani 1 1 d . . . . .
H32 H 1.210249 0.217132 0.079333 0.020 Uiso 1 1 calc R U . . .
C33 C 1.27624(19) 0.07284(17) 0.06803(16) 0.0155(5) Uani 1 1 d . . . . .
C34 C 1.3482(2) 0.04095(18) 0.13117(16) 0.0161(5) Uani 1 1 d . . . . .
H34 H 1.342198 0.077973 0.169709 0.019 Uiso 1 1 calc R U . . .
C35 C 1.4287(2) -0.04716(18) 0.13503(16) 0.0168(5) Uani 1 1 d . . . . .
C36 C 1.4420(2) -0.10540(18) 0.07936(17) 0.0197(5) Uani 1 1 d . . . . .
H36 H 1.495312 -0.165121 0.084910 0.024 Uiso 1 1 calc R U . . .
C37 C 1.3731(2) -0.07167(18) 0.01516(17) 0.0187(5) Uani 1 1 d . . . . .
H37 H 1.381512 -0.107980 -0.024315 0.022 Uiso 1 1 calc R U . . .
C38 C 1.2913(2) 0.01627(18) 0.00935(16) 0.0173(5) Uani 1 1 d . . . . .
H38 H 1.245842 0.037960 -0.034184 0.021 Uiso 1 1 calc R U . . .
C39 C 0.84731(19) 0.40559(17) -0.01441(15) 0.0144(4) Uani 1 1 d . . . . .
H39 H 0.882813 0.453253 -0.006396 0.017 Uiso 1 1 calc R U . . .
C40 C 0.7409(2) 0.44833(17) -0.05086(15) 0.0152(5) Uani 1 1 d . . . . .
C41 C 0.6887(2) 0.54784(18) -0.04940(15) 0.0159(5) Uani 1 1 d . . . . .
H41 H 0.720846 0.583960 -0.025271 0.019 Uiso 1 1 calc R U . . .
C42 C 0.5895(2) 0.59180(18) -0.08397(15) 0.0166(5) Uani 1 1 d . . . . .
C43 C 0.5381(2) 0.54235(19) -0.12167(16) 0.0197(5) Uani 1 1 d . . . . .
H43 H 0.471349 0.573714 -0.144578 0.024 Uiso 1 1 calc R U . . .
C44 C 0.5899(2) 0.44457(19) -0.12393(17) 0.0211(5) Uani 1 1 d . . . . .
H44 H 0.557440 0.409431 -0.148760 0.025 Uiso 1 1 calc R U . . .
C45 C 0.6894(2) 0.39842(18) -0.08967(16) 0.0180(5) Uani 1 1 d . . . . .
H45 H 0.722910 0.332939 -0.092407 0.022 Uiso 1 1 calc R U . . .
C46 C 0.8910(2) 0.10002(18) 0.22637(16) 0.0181(5) Uani 1 1 d . . . . .
C47 C 0.9802(2) 0.0470(2) 0.27252(18) 0.0250(6) Uani 1 1 d . . . . .
H47 H 1.024579 -0.011735 0.261458 0.030 Uiso 1 1 calc R U . . .
C48 C 1.0023(2) 0.0825(2) 0.33492(18) 0.0252(6) Uani 1 1 d . . . . .
H48 H 1.061800 0.047851 0.366116 0.030 Uiso 1 1 calc R U . . .
C49 C 0.9354(2) 0.16991(19) 0.35076(16) 0.0198(5) Uani 1 1 d . . . . .
C50 C 0.8486(2) 0.22436(18) 0.30242(17) 0.0204(5) Uani 1 1 d . . . . .
H50 H 0.806399 0.284625 0.311862 0.024 Uiso 1 1 calc R U . . .
C51 C 0.8251(2) 0.18911(18) 0.24045(16) 0.0193(5) Uani 1 1 d . . . . .
H51 H 0.766307 0.224384 0.208705 0.023 Uiso 1 1 calc R U . . .
C52 C 0.9523(2) 0.2032(2) 0.42391(17) 0.0245(6) Uani 1 1 d . . . . .
C53 C 0.1851(3) 0.7656(2) 0.3153(2) 0.0375(7) Uani 1 1 d . . . . .
H53A H 0.112049 0.746175 0.348322 0.045 Uiso 1 1 calc R U . . .
H53B H 0.204990 0.812879 0.338939 0.045 Uiso 1 1 calc R U . . .
Cl1 Cl 0.28922(9) 0.65486(6) 0.32854(7) 0.0584(3) Uani 1 1 d . . . . .
Cl2 Cl 0.17403(7) 0.82736(6) 0.20381(5) 0.03666(18) Uani 1 1 d . . . . .
F1 F 0.59999(15) 0.36509(13) 0.36398(14) 0.0420(5) Uani 1 1 d . . . . .
F2 F 0.51409(16) 0.50912(14) 0.29292(12) 0.0403(4) Uani 1 1 d . . . . .
F3 F 0.46382(16) 0.44716(17) 0.43253(12) 0.0489(5) Uani 1 1 d . . . . .
F4 F 0.94753(13) 0.30517(12) 0.40120(10) 0.0275(3) Uani 1 1 d . . . . .
F5 F 0.86952(19) 0.17980(18) 0.49448(12) 0.0556(6) Uani 1 1 d . . . . .
F6 F 1.05067(17) 0.16023(14) 0.45113(13) 0.0467(5) Uani 1 1 d . . . . .
N1 N 0.80908(16) 0.68418(14) 0.54688(12) 0.0136(4) Uani 1 1 d . . . . .
N2 N 1.25620(19) 0.42942(19) 0.84814(14) 0.0251(5) Uani 1 1 d . . . . .
N3 N 0.34320(18) 0.89041(17) 0.41104(14) 0.0221(5) Uani 1 1 d . . . . .
N4 N 0.91333(17) 0.11597(15) 0.05104(13) 0.0164(4) Uani 1 1 d . . . . .
N5 N 1.50686(18) -0.07743(16) 0.19928(14) 0.0202(4) Uani 1 1 d . . . . .
N6 N 0.53398(18) 0.69507(16) -0.07935(14) 0.0197(4) Uani 1 1 d . . . . .
O1 O 0.72015(15) 0.76400(13) 0.76350(11) 0.0218(4) Uani 1 1 d . . . . .
O2 O 0.97763(13) 0.61624(12) 0.45446(11) 0.0165(3) Uani 1 1 d . . . . .
O3 O 0.86026(14) 0.78291(12) 0.38867(11) 0.0171(3) Uani 1 1 d . . . . .
O4 O 1.32487(17) 0.35070(17) 0.87119(15) 0.0381(5) Uani 1 1 d . . . . .
O5 O 1.26983(16) 0.51577(16) 0.84366(14) 0.0318(5) Uani 1 1 d . . . . .
O6 O 0.39888(17) 0.81163(15) 0.39672(13) 0.0317(5) Uani 1 1 d . . . . .
O7 O 0.27415(16) 0.94992(15) 0.36508(12) 0.0286(4) Uani 1 1 d . . . . .
O8 O 1.04822(15) 0.35323(13) 0.05388(12) 0.0214(4) Uani 1 1 d . . . . .
O9 O 0.73760(15) 0.07112(14) 0.15476(12) 0.0237(4) Uani 1 1 d . . . . .
O10 O 0.91760(16) -0.05283(13) 0.16630(12) 0.0245(4) Uani 1 1 d . . . . .
O11 O 1.57554(17) -0.15676(15) 0.20459(13) 0.0319(5) Uani 1 1 d . . . . .
O12 O 1.49989(16) -0.02156(14) 0.24370(13) 0.0268(4) Uani 1 1 d . . . . .
O13 O 0.57484(16) 0.73538(13) -0.04039(12) 0.0255(4) Uani 1 1 d . . . . .
O14 O 0.44863(16) 0.73480(15) -0.11349(13) 0.0298(4) Uani 1 1 d . . . . .
S1 S 0.86809(5) 0.67870(4) 0.44758(4) 0.01307(12) Uani 1 1 d . . . . .
S2 S 0.85863(5) 0.05059(4) 0.15021(4) 0.01771(13) 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'
S S 0.1246 0.1234 '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'
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
N1 C1 C2 106.77(18) . .
N1 C1 H1A 110.4 . .
C2 C1 H1A 110.4 . .
N1 C1 H1B 110.4 . .
C2 C1 H1B 110.4 . .
H1A C1 H1B 108.6 . .
C6 C2 C3 117.1(2) . .
C6 C2 C1 125.2(2) . .
C3 C2 C1 117.59(19) . .
O1 C3 C4 121.7(2) . .
O1 C3 C2 121.3(2) . .
C4 C3 C2 117.0(2) . .
C13 C4 C3 116.5(2) . .
C13 C4 C5 124.5(2) . .
C3 C4 C5 119.0(2) . .
N1 C5 C4 110.89(18) . .
N1 C5 H5A 109.5 . .
C4 C5 H5A 109.5 . .
N1 C5 H5B 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 108.0 . .
C2 C6 C7 128.5(2) . .
C2 C6 H6 115.7 . .
C7 C6 H6 115.7 . .
C8 C7 C12 118.6(2) . .
C8 C7 C6 117.5(2) . .
C12 C7 C6 123.8(2) . .
C9 C8 C7 118.9(2) . .
C9 C8 H8 120.5 . .
C7 C8 H8 120.5 . .
C8 C9 C10 123.0(2) . .
C8 C9 N2 118.0(2) . .
C10 C9 N2 119.0(2) . .
C9 C10 C11 117.9(2) . .
C9 C10 H10 121.0 . .
C11 C10 H10 121.0 . .
C12 C11 C10 120.3(2) . .
C12 C11 H11 119.8 . .
C10 C11 H11 119.8 . .
C11 C12 C7 121.1(2) . .
C11 C12 H12 119.5 . .
C7 C12 H12 119.5 . .
C4 C13 C14 130.3(2) . .
C4 C13 H13 114.9 . .
C14 C13 H13 114.9 . .
C15 C14 C19 117.7(2) . .
C15 C14 C13 125.8(2) . .
C19 C14 C13 116.5(2) . .
C16 C15 C14 119.0(2) . .
C16 C15 H15 120.5 . .
C14 C15 H15 120.5 . .
C15 C16 C17 123.6(2) . .
C15 C16 N3 118.3(2) . .
C17 C16 N3 118.2(2) . .
C18 C17 C16 117.4(2) . .
C18 C17 H17 121.3 . .
C16 C17 H17 121.3 . .
C19 C18 C17 120.4(2) . .
C19 C18 H18 119.8 . .
C17 C18 H18 119.8 . .
C18 C19 C14 121.8(2) . .
C18 C19 H19 119.1 . .
C14 C19 H19 119.1 . .
C21 C20 C25 121.7(2) . .
C21 C20 S1 118.84(17) . .
C25 C20 S1 119.38(17) . .
C22 C21 C20 118.9(2) . .
C22 C21 H21 120.5 . .
C20 C21 H21 120.5 . .
C21 C22 C23 119.6(2) . .
C21 C22 H22 120.2 . .
C23 C22 H22 120.2 . .
C22 C23 C24 121.3(2) . .
C22 C23 C26 119.2(2) . .
C24 C23 C26 119.4(2) . .
C25 C24 C23 119.2(2) . .
C25 C24 H24 120.4 . .
C23 C24 H24 120.4 . .
C24 C25 C20 119.2(2) . .
C24 C25 H25 120.4 . .
C20 C25 H25 120.4 . .
F3 C26 F2 107.2(2) . .
F3 C26 F1 106.1(2) . .
F2 C26 F1 105.2(2) . .
F3 C26 C23 112.1(2) . .
F2 C26 C23 112.8(2) . .
F1 C26 C23 112.9(2) . .
N4 C27 C28 111.55(18) . .
N4 C27 H27A 109.3 . .
C28 C27 H27A 109.3 . .
N4 C27 H27B 109.3 . .
C28 C27 H27B 109.3 . .
H27A C27 H27B 108.0 . .
C32 C28 C29 118.6(2) . .
C32 C28 C27 123.6(2) . .
C29 C28 C27 117.80(19) . .
O8 C29 C28 121.5(2) . .
O8 C29 C30 121.1(2) . .
C28 C29 C30 117.4(2) . .
C39 C30 C29 117.5(2) . .
C39 C30 C31 123.6(2) . .
C29 C30 C31 118.86(19) . .
N4 C31 C30 113.31(18) . .
N4 C31 H31A 108.9 . .
C30 C31 H31A 108.9 . .
N4 C31 H31B 108.9 . .
C30 C31 H31B 108.9 . .
H31A C31 H31B 107.7 . .
C28 C32 C33 127.1(2) . .
C28 C32 H32 116.5 . .
C33 C32 H32 116.5 . .
C34 C33 C38 118.5(2) . .
C34 C33 C32 118.5(2) . .
C38 C33 C32 123.0(2) . .
C35 C34 C33 118.6(2) . .
C35 C34 H34 120.7 . .
C33 C34 H34 120.7 . .
C36 C35 C34 123.4(2) . .
C36 C35 N5 118.5(2) . .
C34 C35 N5 118.0(2) . .
C37 C36 C35 117.8(2) . .
C37 C36 H36 121.1 . .
C35 C36 H36 121.1 . .
C36 C37 C38 120.4(2) . .
C36 C37 H37 119.8 . .
C38 C37 H37 119.8 . .
C37 C38 C33 121.3(2) . .
C37 C38 H38 119.4 . .
C33 C38 H38 119.4 . .
C30 C39 C40 129.2(2) . .
C30 C39 H39 115.4 . .
C40 C39 H39 115.4 . .
C41 C40 C45 117.5(2) . .
C41 C40 C39 117.6(2) . .
C45 C40 C39 124.9(2) . .
C42 C41 C40 119.7(2) . .
C42 C41 H41 120.2 . .
C40 C41 H41 120.2 . .
C41 C42 C43 122.9(2) . .
C41 C42 N6 118.9(2) . .
C43 C42 N6 118.2(2) . .
C44 C43 C42 117.6(2) . .
C44 C43 H43 121.2 . .
C42 C43 H43 121.2 . .
C43 C44 C45 120.8(2) . .
C43 C44 H44 119.6 . .
C45 C44 H44 119.6 . .
C44 C45 C40 121.5(2) . .
C44 C45 H45 119.2 . .
C40 C45 H45 119.2 . .
C51 C46 C47 121.3(2) . .
C51 C46 S2 119.51(19) . .
C47 C46 S2 119.12(19) . .
C48 C47 C46 119.3(2) . .
C48 C47 H47 120.3 . .
C46 C47 H47 120.3 . .
C47 C48 C49 119.6(2) . .
C47 C48 H48 120.2 . .
C49 C48 H48 120.2 . .
C48 C49 C50 120.7(2) . .
C48 C49 C52 119.7(2) . .
C50 C49 C52 119.5(2) . .
C51 C50 C49 120.1(2) . .
C51 C50 H50 119.9 . .
C49 C50 H50 119.9 . .
C50 C51 C46 118.8(2) . .
C50 C51 H51 120.6 . .
C46 C51 H51 120.6 . .
F6 C52 F4 107.0(2) . .
F6 C52 F5 107.5(2) . .
F4 C52 F5 104.7(2) . .
F6 C52 C49 113.0(2) . .
F4 C52 C49 112.8(2) . .
F5 C52 C49 111.4(2) . .
Cl2 C53 Cl1 111.00(18) . .
Cl2 C53 H53A 109.4 . .
Cl1 C53 H53A 109.4 . .
Cl2 C53 H53B 109.4 . .
Cl1 C53 H53B 109.4 . .
H53A C53 H53B 108.0 . .
C5 N1 C1 111.69(18) . .
C5 N1 S1 114.86(14) . .
C1 N1 S1 119.44(15) . .
O4 N2 O5 124.2(2) . .
O4 N2 C9 117.9(2) . .
O5 N2 C9 117.9(2) . .
O6 N3 O7 123.5(2) . .
O6 N3 C16 118.3(2) . .
O7 N3 C16 118.2(2) . .
C31 N4 C27 113.00(18) . .
C31 N4 S2 120.58(16) . .
C27 N4 S2 120.02(16) . .
O12 N5 O11 123.9(2) . .
O12 N5 C35 118.1(2) . .
O11 N5 C35 118.1(2) . .
O13 N6 O14 123.8(2) . .
O13 N6 C42 118.06(19) . .
O14 N6 C42 118.1(2) . .
O2 S1 O3 119.48(10) . .
O2 S1 N1 107.30(10) . .
O3 S1 N1 106.97(10) . .
O2 S1 C20 109.16(10) . .
O3 S1 C20 107.49(10) . .
N1 S1 C20 105.63(10) . .
O10 S2 O9 120.31(11) . .
O10 S2 N4 106.42(11) . .
O9 S2 N4 106.81(11) . .
O10 S2 C46 107.11(11) . .
O9 S2 C46 107.55(11) . .
N4 S2 C46 108.18(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.479(3) .
C1 C2 1.510(3) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 C6 1.338(3) .
C2 C3 1.507(3) .
C3 O1 1.221(3) .
C3 C4 1.493(3) .
C4 C13 1.352(3) .
C4 C5 1.503(3) .
C5 N1 1.472(3) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.466(3) .
C6 H6 0.9300 .
C7 C8 1.398(3) .
C7 C12 1.405(3) .
C8 C9 1.384(3) .
C8 H8 0.9300 .
C9 C10 1.385(4) .
C9 N2 1.473(3) .
C10 C11 1.392(4) .
C10 H10 0.9300 .
C11 C12 1.388(3) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C14 1.462(3) .
C13 H13 0.9300 .
C14 C15 1.403(3) .
C14 C19 1.407(3) .
C15 C16 1.377(3) .
C15 H15 0.9300 .
C16 C17 1.388(4) .
C16 N3 1.471(3) .
C17 C18 1.385(4) .
C17 H17 0.9300 .
C18 C19 1.383(3) .
C18 H18 0.9300 .
C19 H19 0.9300 .
C20 C21 1.386(3) .
C20 C25 1.394(3) .
C20 S1 1.771(2) .
C21 C22 1.386(3) .
C21 H21 0.9300 .
C22 C23 1.389(3) .
C22 H22 0.9300 .
C23 C24 1.391(3) .
C23 C26 1.498(3) .
C24 C25 1.384(3) .
C24 H24 0.9300 .
C25 H25 0.9300 .
C26 F3 1.323(3) .
C26 F2 1.326(3) .
C26 F1 1.344(3) .
C27 N4 1.464(3) .
C27 C28 1.513(3) .
C27 H27A 0.9700 .
C27 H27B 0.9700 .
C28 C32 1.340(3) .
C28 C29 1.504(3) .
C29 O8 1.219(3) .
C29 C30 1.506(3) .
C30 C39 1.350(3) .
C30 C31 1.522(3) .
C31 N4 1.463(3) .
C31 H31A 0.9700 .
C31 H31B 0.9700 .
C32 C33 1.469(3) .
C32 H32 0.9300 .
C33 C34 1.401(3) .
C33 C38 1.406(3) .
C34 C35 1.389(3) .
C34 H34 0.9300 .
C35 C36 1.386(3) .
C35 N5 1.472(3) .
C36 C37 1.385(3) .
C36 H36 0.9300 .
C37 C38 1.393(3) .
C37 H37 0.9300 .
C38 H38 0.9300 .
C39 C40 1.471(3) .
C39 H39 0.9300 .
C40 C41 1.404(3) .
C40 C45 1.406(3) .
C41 C42 1.381(3) .
C41 H41 0.9300 .
C42 C43 1.387(3) .
C42 N6 1.475(3) .
C43 C44 1.385(3) .
C43 H43 0.9300 .
C44 C45 1.386(3) .
C44 H44 0.9300 .
C45 H45 0.9300 .
C46 C51 1.389(3) .
C46 C47 1.392(3) .
C46 S2 1.774(2) .
C47 C48 1.381(4) .
C47 H47 0.9300 .
C48 C49 1.385(4) .
C48 H48 0.9300 .
C49 C50 1.391(3) .
C49 C52 1.498(4) .
C50 C51 1.381(3) .
C50 H50 0.9300 .
C51 H51 0.9300 .
C52 F6 1.320(3) .
C52 F4 1.334(3) .
C52 F5 1.342(3) .
C53 Cl2 1.747(3) .
C53 Cl1 1.757(3) .
C53 H53A 0.9700 .
C53 H53B 0.9700 .
N1 S1 1.641(2) .
N2 O4 1.227(3) .
N2 O5 1.230(3) .
N3 O6 1.229(3) .
N3 O7 1.230(3) .
N4 S2 1.625(2) .
N5 O12 1.221(3) .
N5 O11 1.224(3) .
N6 O13 1.224(3) .
N6 O14 1.225(3) .
O2 S1 1.4312(16) .
O3 S1 1.4344(17) .
O9 S2 1.4301(19) .
O10 S2 1.4294(18) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C53 H53B O7 0.97 2.46 3.410(4) 167.5 . yes
C53 H53A O2 0.97 2.60 3.503(4) 154.2 1_455 yes
C47 H47 Cl2 0.93 2.86 3.784(3) 171.8 1_645 yes
C31 H31B Cl2 0.97 2.87 3.780(2) 156.8 2_665 yes
C31 H31A O9 0.97 2.40 2.891(3) 110.8 . yes
C27 H27A O10 0.97 2.45 3.339(3) 152.4 2_755 yes
C21 H21 O2 0.93 2.41 3.343(3) 175.3 2_766 yes
C17 H17 F6 0.93 2.49 3.360(3) 155.8 1_465 yes
C5 H5A F3 0.97 2.44 3.408(3) 172.6 2_666 yes
C1 H1B Cl1 0.97 2.92 3.796(2) 151.2 2_666 yes
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
N1 C1 C2 C6 -141.0(2) . . . .
N1 C1 C2 C3 35.6(3) . . . .
C6 C2 C3 O1 -0.2(3) . . . .
C1 C2 C3 O1 -177.0(2) . . . .
C6 C2 C3 C4 -177.7(2) . . . .
C1 C2 C3 C4 5.5(3) . . . .
O1 C3 C4 C13 -16.9(3) . . . .
C2 C3 C4 C13 160.5(2) . . . .
O1 C3 C4 C5 164.2(2) . . . .
C2 C3 C4 C5 -18.3(3) . . . .
C13 C4 C5 N1 169.1(2) . . . .
C3 C4 C5 N1 -12.1(3) . . . .
C3 C2 C6 C7 178.5(2) . . . .
C1 C2 C6 C7 -4.9(4) . . . .
C2 C6 C7 C8 143.1(2) . . . .
C2 C6 C7 C12 -39.5(4) . . . .
C12 C7 C8 C9 1.7(3) . . . .
C6 C7 C8 C9 179.1(2) . . . .
C7 C8 C9 C10 -3.4(4) . . . .
C7 C8 C9 N2 175.8(2) . . . .
C8 C9 C10 C11 2.6(4) . . . .
N2 C9 C10 C11 -176.7(2) . . . .
C9 C10 C11 C12 0.1(4) . . . .
C10 C11 C12 C7 -1.7(4) . . . .
C8 C7 C12 C11 0.8(3) . . . .
C6 C7 C12 C11 -176.5(2) . . . .
C3 C4 C13 C14 -178.8(2) . . . .
C5 C4 C13 C14 0.0(4) . . . .
C4 C13 C14 C15 11.5(4) . . . .
C4 C13 C14 C19 -170.4(2) . . . .
C19 C14 C15 C16 2.2(3) . . . .
C13 C14 C15 C16 -179.7(2) . . . .
C14 C15 C16 C17 -0.2(4) . . . .
C14 C15 C16 N3 -178.7(2) . . . .
C15 C16 C17 C18 -1.9(4) . . . .
N3 C16 C17 C18 176.5(2) . . . .
C16 C17 C18 C19 2.0(4) . . . .
C17 C18 C19 C14 0.0(4) . . . .
C15 C14 C19 C18 -2.1(3) . . . .
C13 C14 C19 C18 179.6(2) . . . .
C25 C20 C21 C22 -0.4(4) . . . .
S1 C20 C21 C22 176.23(19) . . . .
C20 C21 C22 C23 0.6(4) . . . .
C21 C22 C23 C24 -0.7(4) . . . .
C21 C22 C23 C26 -177.1(2) . . . .
C22 C23 C24 C25 0.5(4) . . . .
C26 C23 C24 C25 176.9(2) . . . .
C23 C24 C25 C20 -0.2(3) . . . .
C21 C20 C25 C24 0.2(3) . . . .
S1 C20 C25 C24 -176.41(18) . . . .
C22 C23 C26 F3 91.3(3) . . . .
C24 C23 C26 F3 -85.2(3) . . . .
C22 C23 C26 F2 -147.5(2) . . . .
C24 C23 C26 F2 36.0(3) . . . .
C22 C23 C26 F1 -28.4(3) . . . .
C24 C23 C26 F1 155.1(2) . . . .
N4 C27 C28 C32 146.9(2) . . . .
N4 C27 C28 C29 -31.8(3) . . . .
C32 C28 C29 O8 -0.5(3) . . . .
C27 C28 C29 O8 178.3(2) . . . .
C32 C28 C29 C30 177.7(2) . . . .
C27 C28 C29 C30 -3.5(3) . . . .
O8 C29 C30 C39 12.7(3) . . . .
C28 C29 C30 C39 -165.5(2) . . . .
O8 C29 C30 C31 -169.7(2) . . . .
C28 C29 C30 C31 12.0(3) . . . .
C39 C30 C31 N4 -167.4(2) . . . .
C29 C30 C31 N4 15.2(3) . . . .
C29 C28 C32 C33 -176.3(2) . . . .
C27 C28 C32 C33 5.0(4) . . . .
C28 C32 C33 C34 -147.5(2) . . . .
C28 C32 C33 C38 34.2(4) . . . .
C38 C33 C34 C35 -2.1(3) . . . .
C32 C33 C34 C35 179.5(2) . . . .
C33 C34 C35 C36 0.2(4) . . . .
C33 C34 C35 N5 177.6(2) . . . .
C34 C35 C36 C37 1.9(4) . . . .
N5 C35 C36 C37 -175.5(2) . . . .
C35 C36 C37 C38 -1.9(4) . . . .
C36 C37 C38 C33 -0.1(4) . . . .
C34 C33 C38 C37 2.2(4) . . . .
C32 C33 C38 C37 -179.6(2) . . . .
C29 C30 C39 C40 174.9(2) . . . .
C31 C30 C39 C40 -2.5(4) . . . .
C30 C39 C40 C41 164.6(2) . . . .
C30 C39 C40 C45 -17.5(4) . . . .
C45 C40 C41 C42 1.1(3) . . . .
C39 C40 C41 C42 179.1(2) . . . .
C40 C41 C42 C43 -0.7(4) . . . .
C40 C41 C42 N6 178.1(2) . . . .
C41 C42 C43 C44 0.1(4) . . . .
N6 C42 C43 C44 -178.7(2) . . . .
C42 C43 C44 C45 0.0(4) . . . .
C43 C44 C45 C40 0.5(4) . . . .
C41 C40 C45 C44 -1.1(4) . . . .
C39 C40 C45 C44 -178.9(2) . . . .
C51 C46 C47 C48 1.4(4) . . . .
S2 C46 C47 C48 -177.0(2) . . . .
C46 C47 C48 C49 0.1(4) . . . .
C47 C48 C49 C50 -2.2(4) . . . .
C47 C48 C49 C52 174.6(2) . . . .
C48 C49 C50 C51 2.8(4) . . . .
C52 C49 C50 C51 -174.0(2) . . . .
C49 C50 C51 C46 -1.3(4) . . . .
C47 C46 C51 C50 -0.8(4) . . . .
S2 C46 C51 C50 177.54(19) . . . .
C48 C49 C52 F6 17.0(3) . . . .
C50 C49 C52 F6 -166.2(2) . . . .
C48 C49 C52 F4 138.5(2) . . . .
C50 C49 C52 F4 -44.7(3) . . . .
C48 C49 C52 F5 -104.0(3) . . . .
C50 C49 C52 F5 72.8(3) . . . .
C4 C5 N1 C1 57.8(2) . . . .
C4 C5 N1 S1 -162.13(15) . . . .
C2 C1 N1 C5 -69.4(2) . . . .
C2 C1 N1 S1 152.56(16) . . . .
C8 C9 N2 O4 171.5(2) . . . .
C10 C9 N2 O4 -9.2(3) . . . .
C8 C9 N2 O5 -9.5(3) . . . .
C10 C9 N2 O5 169.8(2) . . . .
C15 C16 N3 O6 12.7(3) . . . .
C17 C16 N3 O6 -165.8(2) . . . .
C15 C16 N3 O7 -168.1(2) . . . .
C17 C16 N3 O7 13.4(3) . . . .
C30 C31 N4 C27 -52.6(3) . . . .
C30 C31 N4 S2 99.3(2) . . . .
C28 C27 N4 C31 61.2(2) . . . .
C28 C27 N4 S2 -90.9(2) . . . .
C36 C35 N5 O12 174.9(2) . . . .
C34 C35 N5 O12 -2.7(3) . . . .
C36 C35 N5 O11 -4.6(3) . . . .
C34 C35 N5 O11 177.8(2) . . . .
C41 C42 N6 O13 -4.0(3) . . . .
C43 C42 N6 O13 174.8(2) . . . .
C41 C42 N6 O14 177.1(2) . . . .
C43 C42 N6 O14 -4.1(3) . . . .
C5 N1 S1 O2 -173.02(15) . . . .
C1 N1 S1 O2 -36.19(19) . . . .
C5 N1 S1 O3 57.64(17) . . . .
C1 N1 S1 O3 -165.53(16) . . . .
C5 N1 S1 C20 -56.67(17) . . . .
C1 N1 S1 C20 80.17(18) . . . .
C21 C20 S1 O2 29.8(2) . . . .
C25 C20 S1 O2 -153.52(18) . . . .
C21 C20 S1 O3 160.73(18) . . . .
C25 C20 S1 O3 -22.6(2) . . . .
C21 C20 S1 N1 -85.3(2) . . . .
C25 C20 S1 N1 91.4(2) . . . .
C31 N4 S2 O10 164.08(17) . . . .
C27 N4 S2 O10 -46.0(2) . . . .
C31 N4 S2 O9 34.4(2) . . . .
C27 N4 S2 O9 -175.66(17) . . . .
C31 N4 S2 C46 -81.12(19) . . . .
C27 N4 S2 C46 68.83(19) . . . .
C51 C46 S2 O10 -164.8(2) . . . .
C47 C46 S2 O10 13.6(2) . . . .
C51 C46 S2 O9 -34.2(2) . . . .
C47 C46 S2 O9 144.2(2) . . . .
C51 C46 S2 N4 80.8(2) . . . .
C47 C46 S2 N4 -100.8(2) . . . .
