#------------------------------------------------------------------------------
#$Date: 2025-04-22 19:48:50 +0300 (Tue, 22 Apr 2025) $
#$Revision: 299347 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/51/8105114.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_8105114
loop_
_publ_author_name
'Wang, An-Qi'
'Gao, Ru-Ning'
'Luan, Qing-Hao'
'Wang, Ze-Ping'
'Li, Xiao-Ming'
'Hou, Gui-Ge'
_publ_section_title
;
 Crystal structure and anti-inflammatory activity of
 (3E,5E)-3-(2-fluorobenzylidene)-1-((4-acetamidophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one-methanol-hydrate
 (2/1/1), C53H50F2N6O10S2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              381
_journal_page_last               384
_journal_paper_doi               10.1515/ncrs-2019-0686
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C26 H22 F N3 O4 S, 0.5(C H4 O), 0.5(H2 O)'
_chemical_formula_sum            'C26.5 H25 F N3 O5 S'
_chemical_formula_weight         516.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 112.254(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.088(5)
_cell_length_b                   23.560(9)
_cell_length_c                   15.401(6)
_cell_measurement_reflns_used    3882
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      46.713
_cell_measurement_theta_min      4.797
_cell_volume                     5067(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      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28143
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_min         1.670
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.976
_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    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     664
_refine_ls_number_reflns         11167
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.924
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0509
_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)+(0.0650P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1336
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6078
_reflns_number_total             11167
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0686_suppl.cif
_cod_data_source_block           170627c
_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 H50 F2 N6 O10 S2'
_cod_original_formula_weight         1033.11
_cod_original_formula_moiety         '2(C26 H22 F N3 O4 S), C H4 O, H2 O'
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8105114
_shelx_shelxl_version_number     2017/1
_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   0.974
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_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_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 0.97818(14) 0.15423(9) 0.39036(17) 0.0486(6) Uani 1 1 d . . . . .
H1A H 1.004799 0.161477 0.343126 0.058 Uiso 1 1 calc R U . . .
H1B H 1.019458 0.127037 0.434582 0.058 Uiso 1 1 calc R U . . .
C2 C 0.97799(14) 0.20896(9) 0.44160(15) 0.0429(5) Uani 1 1 d . . . . .
C3 C 0.89913(14) 0.21956(9) 0.47478(17) 0.0464(5) Uani 1 1 d . . . . .
C4 C 0.81519(14) 0.18021(9) 0.44418(15) 0.0428(5) Uani 1 1 d . . . . .
C5 C 0.83011(15) 0.12332(9) 0.40706(17) 0.0516(6) Uani 1 1 d . . . . .
H5A H 0.865535 0.098701 0.459147 0.062 Uiso 1 1 calc R U . . .
H5B H 0.768453 0.105847 0.372906 0.062 Uiso 1 1 calc R U . . .
C6 C 1.04463(15) 0.24978(9) 0.45864(16) 0.0483(6) Uani 1 1 d . . . . .
H6 H 1.032340 0.282366 0.486278 0.058 Uiso 1 1 calc R U . . .
C7 C 1.13302(15) 0.25156(10) 0.44107(17) 0.0512(6) Uani 1 1 d . . . . .
C8 C 1.1754(2) 0.30298(12) 0.4388(2) 0.0818(9) Uani 1 1 d . . . . .
C9 C 1.2606(2) 0.30923(14) 0.4279(3) 0.1062(12) Uani 1 1 d . . . . .
H9 H 1.286065 0.345068 0.427067 0.127 Uiso 1 1 calc R U . . .
C10 C 1.3072(2) 0.26164(15) 0.4184(2) 0.0928(10) Uani 1 1 d . . . . .
H10 H 1.364881 0.264750 0.409958 0.111 Uiso 1 1 calc R U . . .
C11 C 1.26974(18) 0.20974(13) 0.4212(2) 0.0789(9) Uani 1 1 d . . . . .
H11 H 1.302142 0.177347 0.415134 0.095 Uiso 1 1 calc R U . . .
C12 C 1.18477(16) 0.20458(11) 0.43294(19) 0.0625(7) Uani 1 1 d . . . . .
H12 H 1.160906 0.168493 0.435549 0.075 Uiso 1 1 calc R U . . .
C13 C 0.73203(14) 0.19992(10) 0.44364(15) 0.0487(6) Uani 1 1 d . . . . .
H13 H 0.732895 0.237089 0.464274 0.058 Uiso 1 1 calc R U . . .
C14 C 0.63944(15) 0.17069(10) 0.41479(16) 0.0496(6) Uani 1 1 d . . . . .
C15 C 0.55659(16) 0.20101(11) 0.36297(19) 0.0621(7) Uani 1 1 d . . . . .
H15 H 0.563576 0.238500 0.347759 0.075 Uiso 1 1 calc R U . . .
C16 C 0.46006(18) 0.12636(13) 0.3595(2) 0.0700(8) Uani 1 1 d . . . . .
H16 H 0.399008 0.110863 0.341355 0.084 Uiso 1 1 calc R U . . .
C17 C 0.53654(18) 0.09324(12) 0.41103(19) 0.0657(7) Uani 1 1 d . . . . .
H17 H 0.527216 0.056451 0.427786 0.079 Uiso 1 1 calc R U . . .
C18 C 0.62758(16) 0.11539(11) 0.43758(17) 0.0568(6) Uani 1 1 d . . . . .
H18 H 0.680617 0.093174 0.470638 0.068 Uiso 1 1 calc R U . . .
C19 C 0.78102(14) 0.21005(9) 0.21268(15) 0.0442(5) Uani 1 1 d . . . . .
C20 C 0.84062(15) 0.25315(10) 0.20470(17) 0.0541(6) Uani 1 1 d . . . . .
H20 H 0.903330 0.245040 0.211851 0.065 Uiso 1 1 calc R U . . .
C21 C 0.80656(15) 0.30754(10) 0.18627(17) 0.0548(6) Uani 1 1 d . . . . .
H21 H 0.846771 0.336200 0.181320 0.066 Uiso 1 1 calc R U . . .
C22 C 0.71303(14) 0.32068(9) 0.17484(15) 0.0450(5) Uani 1 1 d . . . . .
C23 C 0.65428(14) 0.27787(10) 0.18448(16) 0.0489(6) Uani 1 1 d . . . . .
H23 H 0.591882 0.286038 0.178340 0.059 Uiso 1 1 calc R U . . .
C24 C 0.68874(14) 0.22324(9) 0.20318(16) 0.0485(6) Uani 1 1 d . . . . .
H24 H 0.649035 0.194700 0.209525 0.058 Uiso 1 1 calc R U . . .
C25 C 0.59699(17) 0.40152(11) 0.13364(16) 0.0531(6) Uani 1 1 d . . . . .
C26 C 0.59411(18) 0.46398(11) 0.11424(19) 0.0684(7) Uani 1 1 d . . . . .
H26A H 0.601818 0.470263 0.055914 0.103 Uiso 1 1 calc R U . . .
H26B H 0.644983 0.482509 0.164008 0.103 Uiso 1 1 calc R U . . .
H26C H 0.533689 0.479161 0.110387 0.103 Uiso 1 1 calc R U . . .
C27 C 0.48584(14) 0.52801(9) 0.32655(16) 0.0482(6) Uani 1 1 d . . . . .
H27A H 0.525733 0.555952 0.370180 0.058 Uiso 1 1 calc R U . . .
H27B H 0.513508 0.520602 0.280162 0.058 Uiso 1 1 calc R U . . .
C28 C 0.48671(14) 0.47356(9) 0.37946(15) 0.0422(5) Uani 1 1 d . . . . .
C29 C 0.40569(15) 0.46202(9) 0.41027(16) 0.0475(6) Uani 1 1 d . . . . .
C30 C 0.32475(15) 0.50320(9) 0.38465(15) 0.0445(5) Uani 1 1 d . . . . .
C31 C 0.33812(16) 0.55927(9) 0.34260(16) 0.0504(6) Uani 1 1 d . . . . .
H31A H 0.275955 0.576048 0.308088 0.060 Uiso 1 1 calc R U . . .
H31B H 0.373735 0.585153 0.392630 0.060 Uiso 1 1 calc R U . . .
C32 C 0.55540(15) 0.43366(9) 0.40054(15) 0.0475(6) Uani 1 1 d . . . . .
H32 H 0.542534 0.401185 0.428047 0.057 Uiso 1 1 calc R U . . .
C33 C 0.64581(15) 0.43222(9) 0.38809(15) 0.0463(5) Uani 1 1 d . . . . .
C34 C 0.69202(18) 0.38031(10) 0.39275(17) 0.0580(6) Uani 1 1 d . . . . .
C35 C 0.77977(19) 0.37374(12) 0.38917(18) 0.0652(7) Uani 1 1 d . . . . .
H35 H 0.806916 0.337937 0.392847 0.078 Uiso 1 1 calc R U . . .
C36 C 0.82739(19) 0.42167(13) 0.37994(18) 0.0695(8) Uani 1 1 d . . . . .
H36 H 0.887820 0.418484 0.377447 0.083 Uiso 1 1 calc R U . . .
C37 C 0.78652(17) 0.47386(11) 0.37440(18) 0.0628(7) Uani 1 1 d . . . . .
H37 H 0.819230 0.505957 0.367665 0.075 Uiso 1 1 calc R U . . .
C38 C 0.69760(15) 0.47964(10) 0.37866(16) 0.0514(6) Uani 1 1 d . . . . .
H38 H 0.671303 0.515665 0.375218 0.062 Uiso 1 1 calc R U . . .
C39 C 0.24452(15) 0.48643(10) 0.39359(16) 0.0511(6) Uani 1 1 d . . . . .
H39 H 0.246290 0.450306 0.418527 0.061 Uiso 1 1 calc R U . . .
C40 C 0.15351(15) 0.51695(10) 0.36962(16) 0.0488(6) Uani 1 1 d . . . . .
C41 C 0.06843(17) 0.48632(11) 0.33016(18) 0.0625(7) Uani 1 1 d . . . . .
H41 H 0.072745 0.447542 0.321135 0.075 Uiso 1 1 calc R U . . .
C42 C -0.02342(18) 0.56388(13) 0.3229(2) 0.0692(8) Uani 1 1 d . . . . .
H42 H -0.083632 0.580222 0.306932 0.083 Uiso 1 1 calc R U . . .
C43 C 0.05577(17) 0.59765(11) 0.36404(18) 0.0623(7) Uani 1 1 d . . . . .
H43 H 0.049126 0.635625 0.376893 0.075 Uiso 1 1 calc R U . . .
C44 C 0.14484(16) 0.57419(10) 0.38578(17) 0.0548(6) Uani 1 1 d . . . . .
H44 H 0.199297 0.596647 0.411320 0.066 Uiso 1 1 calc R U . . .
C45 C 0.28154(14) 0.46559(9) 0.16693(15) 0.0449(5) Uani 1 1 d . . . . .
C46 C 0.33941(15) 0.41873(10) 0.17018(16) 0.0491(6) Uani 1 1 d . . . . .
H46 H 0.401104 0.423887 0.171738 0.059 Uiso 1 1 calc R U . . .
C47 C 0.30459(15) 0.36499(10) 0.17106(16) 0.0516(6) Uani 1 1 d . . . . .
H47 H 0.343575 0.333955 0.173603 0.062 Uiso 1 1 calc R U . . .
C48 C 0.21210(15) 0.35574(10) 0.16824(16) 0.0505(6) Uani 1 1 d . . . . .
C49 C 0.15540(15) 0.40318(11) 0.16609(17) 0.0566(6) Uani 1 1 d . . . . .
H49 H 0.093837 0.398223 0.164990 0.068 Uiso 1 1 calc R U . . .
C50 C 0.19014(15) 0.45693(10) 0.16559(16) 0.0521(6) Uani 1 1 d . . . . .
H50 H 0.151775 0.488055 0.164335 0.063 Uiso 1 1 calc R U . . .
C51 C 0.0938(2) 0.28025(13) 0.1597(2) 0.0835(9) Uani 1 1 d . . . . .
C52 C 0.0826(2) 0.21698(13) 0.1502(3) 0.1094(12) Uani 1 1 d . . . . .
H52A H 0.116388 0.199493 0.209992 0.164 Uiso 1 1 calc R U . . .
H52B H 0.108278 0.203645 0.105658 0.164 Uiso 1 1 calc R U . . .
H52C H 0.015898 0.207337 0.128945 0.164 Uiso 1 1 calc R U . . .
C53 C 0.8690(3) 0.44374(17) 0.0881(3) 0.1349(16) Uani 1 1 d . . . . .
H53A H 0.878386 0.479811 0.063821 0.202 Uiso 1 1 calc R U . . .
H53B H 0.822749 0.422088 0.038805 0.202 Uiso 1 1 calc R U . . .
H53C H 0.928621 0.423496 0.111873 0.202 Uiso 1 1 calc R U . . .
F1 F 1.12899(14) 0.35016(7) 0.44754(19) 0.1410(9) Uani 1 1 d . . . . .
F2 F 0.64508(11) 0.33292(6) 0.40313(13) 0.0896(5) Uani 1 1 d . . . . .
N1 N 0.88272(11) 0.12931(7) 0.34497(13) 0.0463(5) Uani 1 1 d . . . . .
N2 N 0.46826(13) 0.17974(10) 0.33394(16) 0.0693(6) Uani 1 1 d . . . . .
N3 N 0.68449(12) 0.37711(8) 0.15384(15) 0.0536(5) Uani 1 1 d . . . . .
H3 H 0.724785 0.401955 0.161330 0.080 Uiso 1 1 calc R U . . .
N4 N 0.38959(12) 0.55156(7) 0.27936(13) 0.0441(4) Uani 1 1 d . . . . .
N5 N -0.01847(14) 0.50905(11) 0.30461(16) 0.0704(6) Uani 1 1 d . . . . .
N6 N 0.18053(13) 0.30004(9) 0.16414(16) 0.0617(6) Uani 1 1 d . . . . .
H6A H 0.213154 0.273420 0.158875 0.092 Uiso 1 1 calc R U . . .
O1 O 0.90128(11) 0.26020(7) 0.52570(12) 0.0628(5) Uani 1 1 d . . . . .
O2 O 0.74164(11) 0.10352(7) 0.20780(12) 0.0683(5) Uani 1 1 d . . . . .
O3 O 0.89140(11) 0.13353(7) 0.18982(12) 0.0655(5) Uani 1 1 d . . . . .
O4 O 0.52587(12) 0.37452(8) 0.12825(14) 0.0758(6) Uani 1 1 d . . . . .
O5 O 0.40497(11) 0.41958(7) 0.45555(13) 0.0656(5) Uani 1 1 d . . . . .
O6 O 0.24555(11) 0.57241(7) 0.14147(11) 0.0619(5) Uani 1 1 d . . . . .
O7 O 0.39125(11) 0.53481(7) 0.12321(12) 0.0629(5) Uani 1 1 d . . . . .
O8 O 0.03128(15) 0.31082(10) 0.1641(2) 0.1393(11) Uani 1 1 d . . . . .
O9 O 0.81749(11) 0.28359(7) 0.66190(14) 0.0796(6) Uani 1 1 d D . . . .
H9A H 0.859197 0.289500 0.717291 0.119 Uiso 1 1 d DR U . . .
H9B H 0.845429 0.275090 0.625092 0.119 Uiso 1 1 d DR U . . .
O10 O 0.83559(15) 0.45229(11) 0.16088(18) 0.0994(7) Uani 1 1 d . . . . .
H10A H 0.875470 0.470354 0.203313 0.149 Uiso 1 1 calc R U . . .
S1 S 0.82334(4) 0.14006(2) 0.23271(4) 0.05086(17) Uani 1 1 d . . . . .
S2 S 0.32634(4) 0.53468(2) 0.17088(4) 0.04829(16) 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'
S S 0.1246 0.1234 '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'
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 113.26(17) . .
N1 C1 H1A 108.9 . .
C2 C1 H1A 108.9 . .
N1 C1 H1B 108.9 . .
C2 C1 H1B 108.9 . .
H1A C1 H1B 107.7 . .
C6 C2 C3 116.8(2) . .
C6 C2 C1 124.3(2) . .
C3 C2 C1 118.92(18) . .
O1 C3 C2 121.32(19) . .
O1 C3 C4 119.9(2) . .
C2 C3 C4 118.8(2) . .
C13 C4 C3 117.9(2) . .
C13 C4 C5 125.59(19) . .
C3 C4 C5 116.16(18) . .
N1 C5 C4 110.99(17) . .
N1 C5 H5A 109.4 . .
C4 C5 H5A 109.4 . .
N1 C5 H5B 109.4 . .
C4 C5 H5B 109.4 . .
H5A C5 H5B 108.0 . .
C2 C6 C7 130.8(2) . .
C2 C6 H6 114.6 . .
C7 C6 H6 114.6 . .
C8 C7 C12 114.7(2) . .
C8 C7 C6 119.7(2) . .
C12 C7 C6 125.4(2) . .
F1 C8 C9 118.2(3) . .
F1 C8 C7 117.4(2) . .
C9 C8 C7 124.4(3) . .
C10 C9 C8 118.3(3) . .
C10 C9 H9 120.9 . .
C8 C9 H9 120.9 . .
C11 C10 C9 120.1(3) . .
C11 C10 H10 120.0 . .
C9 C10 H10 120.0 . .
C10 C11 C12 120.6(3) . .
C10 C11 H11 119.7 . .
C12 C11 H11 119.7 . .
C11 C12 C7 122.0(2) . .
C11 C12 H12 119.0 . .
C7 C12 H12 119.0 . .
C4 C13 C14 128.6(2) . .
C4 C13 H13 115.7 . .
C14 C13 H13 115.7 . .
C18 C14 C15 117.0(2) . .
C18 C14 C13 124.5(2) . .
C15 C14 C13 118.4(2) . .
N2 C15 C14 124.3(2) . .
N2 C15 H15 117.8 . .
C14 C15 H15 117.8 . .
N2 C16 C17 123.7(2) . .
N2 C16 H16 118.2 . .
C17 C16 H16 118.2 . .
C16 C17 C18 118.8(2) . .
C16 C17 H17 120.6 . .
C18 C17 H17 120.6 . .
C14 C18 C17 119.5(2) . .
C14 C18 H18 120.2 . .
C17 C18 H18 120.2 . .
C24 C19 C20 119.1(2) . .
C24 C19 S1 121.09(17) . .
C20 C19 S1 119.81(16) . .
C21 C20 C19 119.8(2) . .
C21 C20 H20 120.1 . .
C19 C20 H20 120.1 . .
C20 C21 C22 121.2(2) . .
C20 C21 H21 119.4 . .
C22 C21 H21 119.4 . .
C23 C22 C21 119.0(2) . .
C23 C22 N3 124.27(19) . .
C21 C22 N3 116.78(19) . .
C24 C23 C22 119.73(19) . .
C24 C23 H23 120.1 . .
C22 C23 H23 120.1 . .
C23 C24 C19 121.2(2) . .
C23 C24 H24 119.4 . .
C19 C24 H24 119.4 . .
O4 C25 N3 123.0(2) . .
O4 C25 C26 122.6(2) . .
N3 C25 C26 114.3(2) . .
C25 C26 H26A 109.5 . .
C25 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C25 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
N4 C27 C28 113.08(17) . .
N4 C27 H27A 109.0 . .
C28 C27 H27A 109.0 . .
N4 C27 H27B 109.0 . .
C28 C27 H27B 109.0 . .
H27A C27 H27B 107.8 . .
C32 C28 C29 116.39(19) . .
C32 C28 C27 124.7(2) . .
C29 C28 C27 118.87(18) . .
O5 C29 C30 120.0(2) . .
O5 C29 C28 121.0(2) . .
C30 C29 C28 118.95(19) . .
C39 C30 C29 117.8(2) . .
C39 C30 C31 125.2(2) . .
C29 C30 C31 116.83(19) . .
N4 C31 C30 111.37(17) . .
N4 C31 H31A 109.4 . .
C30 C31 H31A 109.4 . .
N4 C31 H31B 109.4 . .
C30 C31 H31B 109.4 . .
H31A C31 H31B 108.0 . .
C28 C32 C33 131.5(2) . .
C28 C32 H32 114.2 . .
C33 C32 H32 114.2 . .
C34 C33 C38 114.6(2) . .
C34 C33 C32 119.4(2) . .
C38 C33 C32 125.8(2) . .
C35 C34 F2 118.0(2) . .
C35 C34 C33 125.1(2) . .
F2 C34 C33 116.9(2) . .
C34 C35 C36 117.9(2) . .
C34 C35 H35 121.1 . .
C36 C35 H35 121.1 . .
C37 C36 C35 120.4(2) . .
C37 C36 H36 119.8 . .
C35 C36 H36 119.8 . .
C36 C37 C38 120.8(2) . .
C36 C37 H37 119.6 . .
C38 C37 H37 119.6 . .
C37 C38 C33 121.2(2) . .
C37 C38 H38 119.4 . .
C33 C38 H38 119.4 . .
C30 C39 C40 129.1(2) . .
C30 C39 H39 115.5 . .
C40 C39 H39 115.5 . .
C44 C40 C41 116.6(2) . .
C44 C40 C39 125.0(2) . .
C41 C40 C39 118.4(2) . .
N5 C41 C40 124.2(2) . .
N5 C41 H41 117.9 . .
C40 C41 H41 117.9 . .
N5 C42 C43 123.4(2) . .
N5 C42 H42 118.3 . .
C43 C42 H42 118.3 . .
C44 C43 C42 118.7(2) . .
C44 C43 H43 120.7 . .
C42 C43 H43 120.7 . .
C43 C44 C40 119.9(2) . .
C43 C44 H44 120.1 . .
C40 C44 H44 120.1 . .
C50 C45 C46 119.3(2) . .
C50 C45 S2 120.34(16) . .
C46 C45 S2 120.31(17) . .
C47 C46 C45 119.5(2) . .
C47 C46 H46 120.2 . .
C45 C46 H46 120.2 . .
C46 C47 C48 121.7(2) . .
C46 C47 H47 119.2 . .
C48 C47 H47 119.2 . .
N6 C48 C47 118.0(2) . .
N6 C48 C49 123.9(2) . .
C47 C48 C49 118.1(2) . .
C50 C49 C48 120.4(2) . .
C50 C49 H49 119.8 . .
C48 C49 H49 119.8 . .
C49 C50 C45 121.1(2) . .
C49 C50 H50 119.5 . .
C45 C50 H50 119.5 . .
O8 C51 N6 123.1(3) . .
O8 C51 C52 122.4(3) . .
N6 C51 C52 114.5(3) . .
C51 C52 H52A 109.5 . .
C51 C52 H52B 109.5 . .
H52A C52 H52B 109.5 . .
C51 C52 H52C 109.5 . .
H52A C52 H52C 109.5 . .
H52B C52 H52C 109.5 . .
O10 C53 H53A 109.5 . .
O10 C53 H53B 109.5 . .
H53A C53 H53B 109.5 . .
O10 C53 H53C 109.5 . .
H53A C53 H53C 109.5 . .
H53B C53 H53C 109.5 . .
C5 N1 C1 113.93(18) . .
C5 N1 S1 119.32(14) . .
C1 N1 S1 119.19(15) . .
C15 N2 C16 116.6(2) . .
C25 N3 C22 129.9(2) . .
C25 N3 H3 109.5 . .
C22 N3 H3 120.0 . .
C27 N4 C31 113.05(17) . .
C27 N4 S2 120.14(15) . .
C31 N4 S2 117.31(14) . .
C42 N5 C41 117.2(2) . .
C51 N6 C48 129.1(2) . .
C51 N6 H6A 109.5 . .
C48 N6 H6A 121.2 . .
H9A O9 H9B 109.9 . .
C53 O10 H10A 109.5 . .
O3 S1 O2 120.65(10) . .
O3 S1 N1 105.71(10) . .
O2 S1 N1 105.14(10) . .
O3 S1 C19 107.37(10) . .
O2 S1 C19 107.41(10) . .
N1 S1 C19 110.38(10) . .
O7 S2 O6 120.10(10) . .
O7 S2 N4 106.08(10) . .
O6 S2 N4 105.65(10) . .
O7 S2 C45 108.31(10) . .
O6 S2 C45 107.06(10) . .
N4 S2 C45 109.30(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.465(2) .
C1 C2 1.512(3) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 C6 1.343(3) .
C2 C3 1.483(3) .
C3 O1 1.230(3) .
C3 C4 1.495(3) .
C4 C13 1.335(3) .
C4 C5 1.507(3) .
C5 N1 1.463(3) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.458(3) .
C6 H6 0.9300 .
C7 C8 1.376(3) .
C7 C12 1.387(3) .
C8 F1 1.347(3) .
C8 C9 1.366(4) .
C9 C10 1.361(4) .
C9 H9 0.9300 .
C10 C11 1.355(4) .
C10 H10 0.9300 .
C11 C12 1.366(3) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C14 1.467(3) .
C13 H13 0.9300 .
C14 C18 1.378(3) .
C14 C15 1.398(3) .
C15 N2 1.333(3) .
C15 H15 0.9300 .
C16 N2 1.338(3) .
C16 C17 1.370(3) .
C16 H16 0.9300 .
C17 C18 1.379(3) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C19 C24 1.379(3) .
C19 C20 1.392(3) .
C19 S1 1.753(2) .
C20 C21 1.370(3) .
C20 H20 0.9300 .
C21 C22 1.389(3) .
C21 H21 0.9300 .
C22 C23 1.387(3) .
C22 N3 1.397(3) .
C23 C24 1.377(3) .
C23 H23 0.9300 .
C24 H24 0.9300 .
C25 O4 1.223(3) .
C25 N3 1.364(3) .
C25 C26 1.499(3) .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 0.9600 .
C27 N4 1.465(2) .
C27 C28 1.517(3) .
C27 H27A 0.9700 .
C27 H27B 0.9700 .
C28 C32 1.345(3) .
C28 C29 1.494(3) .
C29 O5 1.222(2) .
C29 C30 1.491(3) .
C30 C39 1.329(3) .
C30 C31 1.518(3) .
C31 N4 1.469(3) .
C31 H31A 0.9700 .
C31 H31B 0.9700 .
C32 C33 1.448(3) .
C32 H32 0.9300 .
C33 C34 1.396(3) .
C33 C38 1.402(3) .
C34 C35 1.355(3) .
C34 F2 1.364(3) .
C35 C36 1.374(4) .
C35 H35 0.9300 .
C36 C37 1.364(3) .
C36 H36 0.9300 .
C37 C38 1.375(3) .
C37 H37 0.9300 .
C38 H38 0.9300 .
C39 C40 1.468(3) .
C39 H39 0.9300 .
C40 C44 1.387(3) .
C40 C41 1.395(3) .
C41 N5 1.330(3) .
C41 H41 0.9300 .
C42 N5 1.330(3) .
C42 C43 1.374(3) .
C42 H42 0.9300 .
C43 C44 1.372(3) .
C43 H43 0.9300 .
C44 H44 0.9300 .
C45 C50 1.387(3) .
C45 C46 1.397(3) .
C45 S2 1.754(2) .
C46 C47 1.373(3) .
C46 H46 0.9300 .
C47 C48 1.397(3) .
C47 H47 0.9300 .
C48 N6 1.389(3) .
C48 C49 1.400(3) .
C49 C50 1.372(3) .
C49 H49 0.9300 .
C50 H50 0.9300 .
C51 O8 1.209(3) .
C51 N6 1.366(3) .
C51 C52 1.501(4) .
C52 H52A 0.9600 .
C52 H52B 0.9600 .
C52 H52C 0.9600 .
C53 O10 1.407(4) .
C53 H53A 0.9600 .
C53 H53B 0.9600 .
C53 H53C 0.9600 .
N1 S1 1.638(2) .
N3 H3 0.8200 .
N4 S2 1.6287(19) .
N6 H6A 0.8200 .
O2 S1 1.4317(16) .
O3 S1 1.4241(17) .
O6 S2 1.4365(15) .
O7 S2 1.4291(16) .
O9 H9A 0.8582 .
O9 H9B 0.8486 .
O10 H10A 0.8200 .
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
O10 H10A N5 0.82 1.98 2.801(3) 174.4 1_655 yes
O9 H9B O1 0.85 2.04 2.883(3) 173.5 . yes
O9 H9A N2 0.86 2.05 2.894(3) 165.8 4_666 yes
N6 H6A O9 0.82 2.06 2.865(3) 168.6 4_565 yes
N3 H3 O10 0.82 2.05 2.857(3) 166.8 . yes
C53 H53B O6 0.96 2.57 3.317(4) 134.4 3_665 yes
C49 H49 O8 0.93 2.26 2.864(3) 121.7 . yes
C46 H46 O4 0.93 2.51 3.285(3) 141.0 . yes
C42 H42 O2 0.93 2.37 3.280(3) 165.2 2 yes
C27 H27A O5 0.97 2.55 3.364(3) 141.4 3_666 yes
C27 H27A O3 0.97 2.58 3.167(3) 119.4 2_655 yes
C26 H26C O7 0.96 2.59 3.535(3) 168.7 . yes
C23 H23 O4 0.93 2.31 2.901(3) 120.8 . yes
C16 H16 O6 0.93 2.47 3.347(3) 158.0 2_545 yes
C15 H15 F2 0.93 2.53 3.346(3) 146.9 . yes
C9 H9 O5 0.93 2.43 3.314(3) 159.2 1_655 yes
C1 H1A O3 0.97 2.42 2.903(3) 110.0 . 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 -154.6(2) . . . .
N1 C1 C2 C3 24.6(3) . . . .
C6 C2 C3 O1 -9.0(3) . . . .
C1 C2 C3 O1 171.7(2) . . . .
C6 C2 C3 C4 170.1(2) . . . .
C1 C2 C3 C4 -9.1(3) . . . .
O1 C3 C4 C13 23.5(3) . . . .
C2 C3 C4 C13 -155.7(2) . . . .
O1 C3 C4 C5 -162.6(2) . . . .
C2 C3 C4 C5 18.2(3) . . . .
C13 C4 C5 N1 130.7(2) . . . .
C3 C4 C5 N1 -42.6(3) . . . .
C3 C2 C6 C7 175.8(2) . . . .
C1 C2 C6 C7 -5.0(4) . . . .
C2 C6 C7 C8 161.0(3) . . . .
C2 C6 C7 C12 -24.3(4) . . . .
C12 C7 C8 F1 -179.2(3) . . . .
C6 C7 C8 F1 -4.0(4) . . . .
C12 C7 C8 C9 1.1(5) . . . .
C6 C7 C8 C9 176.4(3) . . . .
F1 C8 C9 C10 -179.5(3) . . . .
C7 C8 C9 C10 0.1(6) . . . .
C8 C9 C10 C11 -1.0(6) . . . .
C9 C10 C11 C12 0.5(5) . . . .
C10 C11 C12 C7 0.9(5) . . . .
C8 C7 C12 C11 -1.6(4) . . . .
C6 C7 C12 C11 -176.6(2) . . . .
C3 C4 C13 C14 178.4(2) . . . .
C5 C4 C13 C14 5.1(4) . . . .
C4 C13 C14 C18 42.9(4) . . . .
C4 C13 C14 C15 -139.1(3) . . . .
C18 C14 C15 N2 -0.7(4) . . . .
C13 C14 C15 N2 -178.8(2) . . . .
N2 C16 C17 C18 -0.7(4) . . . .
C15 C14 C18 C17 -1.6(4) . . . .
C13 C14 C18 C17 176.4(2) . . . .
C16 C17 C18 C14 2.3(4) . . . .
C24 C19 C20 C21 -1.0(3) . . . .
S1 C19 C20 C21 178.06(19) . . . .
C19 C20 C21 C22 -0.3(4) . . . .
C20 C21 C22 C23 1.5(4) . . . .
C20 C21 C22 N3 -178.4(2) . . . .
C21 C22 C23 C24 -1.3(3) . . . .
N3 C22 C23 C24 178.5(2) . . . .
C22 C23 C24 C19 0.1(3) . . . .
C20 C19 C24 C23 1.1(3) . . . .
S1 C19 C24 C23 -177.91(17) . . . .
N4 C27 C28 C32 155.9(2) . . . .
N4 C27 C28 C29 -23.4(3) . . . .
C32 C28 C29 O5 3.0(3) . . . .
C27 C28 C29 O5 -177.7(2) . . . .
C32 C28 C29 C30 -176.85(19) . . . .
C27 C28 C29 C30 2.5(3) . . . .
O5 C29 C30 C39 -14.7(3) . . . .
C28 C29 C30 C39 165.1(2) . . . .
O5 C29 C30 C31 170.3(2) . . . .
C28 C29 C30 C31 -9.9(3) . . . .
C39 C30 C31 N4 -136.6(2) . . . .
C29 C30 C31 N4 38.0(3) . . . .
C29 C28 C32 C33 -175.0(2) . . . .
C27 C28 C32 C33 5.7(4) . . . .
C28 C32 C33 C34 -162.9(2) . . . .
C28 C32 C33 C38 22.5(4) . . . .
C38 C33 C34 C35 0.2(4) . . . .
C32 C33 C34 C35 -174.9(2) . . . .
C38 C33 C34 F2 179.2(2) . . . .
C32 C33 C34 F2 4.0(3) . . . .
F2 C34 C35 C36 -179.2(2) . . . .
C33 C34 C35 C36 -0.2(4) . . . .
C34 C35 C36 C37 -0.2(4) . . . .
C35 C36 C37 C38 0.5(4) . . . .
C36 C37 C38 C33 -0.5(4) . . . .
C34 C33 C38 C37 0.1(3) . . . .
C32 C33 C38 C37 174.9(2) . . . .
C29 C30 C39 C40 -176.9(2) . . . .
C31 C30 C39 C40 -2.4(4) . . . .
C30 C39 C40 C44 -40.9(4) . . . .
C30 C39 C40 C41 141.3(3) . . . .
C44 C40 C41 N5 2.6(4) . . . .
C39 C40 C41 N5 -179.4(2) . . . .
N5 C42 C43 C44 1.5(4) . . . .
C42 C43 C44 C40 -2.6(4) . . . .
C41 C40 C44 C43 0.7(3) . . . .
C39 C40 C44 C43 -177.2(2) . . . .
C50 C45 C46 C47 0.6(3) . . . .
S2 C45 C46 C47 177.23(18) . . . .
C45 C46 C47 C48 0.4(3) . . . .
C46 C47 C48 N6 176.5(2) . . . .
C46 C47 C48 C49 -1.1(4) . . . .
N6 C48 C49 C50 -176.6(2) . . . .
C47 C48 C49 C50 0.8(3) . . . .
C48 C49 C50 C45 0.2(4) . . . .
C46 C45 C50 C49 -0.9(3) . . . .
S2 C45 C50 C49 -177.51(18) . . . .
C4 C5 N1 C1 60.4(2) . . . .
C4 C5 N1 S1 -89.1(2) . . . .
C2 C1 N1 C5 -51.1(2) . . . .
C2 C1 N1 S1 98.5(2) . . . .
C14 C15 N2 C16 2.2(4) . . . .
C17 C16 N2 C15 -1.5(4) . . . .
O4 C25 N3 C22 -2.4(4) . . . .
C26 C25 N3 C22 -179.8(2) . . . .
C23 C22 N3 C25 -4.1(4) . . . .
C21 C22 N3 C25 175.7(2) . . . .
C28 C27 N4 C31 53.3(2) . . . .
C28 C27 N4 S2 -92.2(2) . . . .
C30 C31 N4 C27 -60.9(2) . . . .
C30 C31 N4 S2 85.63(19) . . . .
C43 C42 N5 C41 1.6(4) . . . .
C40 C41 N5 C42 -3.7(4) . . . .
O8 C51 N6 C48 -4.3(5) . . . .
C52 C51 N6 C48 176.5(3) . . . .
C47 C48 N6 C51 -179.1(3) . . . .
C49 C48 N6 C51 -1.7(4) . . . .
C5 N1 S1 O3 -169.56(15) . . . .
C1 N1 S1 O3 42.58(18) . . . .
C5 N1 S1 O2 -40.90(17) . . . .
C1 N1 S1 O2 171.23(15) . . . .
C5 N1 S1 C19 74.64(17) . . . .
C1 N1 S1 C19 -73.23(17) . . . .
C24 C19 S1 O3 148.55(19) . . . .
C20 C19 S1 O3 -30.4(2) . . . .
C24 C19 S1 O2 17.4(2) . . . .
C20 C19 S1 O2 -161.58(18) . . . .
C24 C19 S1 N1 -96.69(19) . . . .
C20 C19 S1 N1 84.3(2) . . . .
C27 N4 S2 O7 -41.03(17) . . . .
C31 N4 S2 O7 174.94(14) . . . .
C27 N4 S2 O6 -169.56(15) . . . .
C31 N4 S2 O6 46.41(17) . . . .
C27 N4 S2 C45 75.55(17) . . . .
C31 N4 S2 C45 -68.48(16) . . . .
C50 C45 S2 O7 -149.39(18) . . . .
C46 C45 S2 O7 34.1(2) . . . .
C50 C45 S2 O6 -18.5(2) . . . .
C46 C45 S2 O6 164.91(17) . . . .
C50 C45 S2 N4 95.45(19) . . . .
C46 C45 S2 N4 -81.1(2) . . . .
