#------------------------------------------------------------------------------
#$Date: 2025-01-29 05:24:22 +0200 (Wed, 29 Jan 2025) $
#$Revision: 297518 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/33/2023363.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023363
loop_
_publ_author_name
'Aliyeva, Khatira N.'
'Hökelek, Tuncer'
'Khrustalev, Victor N.'
'Rzayev, Rovnag M.'
'Bhattarai, Ajaya'
'Maharramov, Abel M.'
'Shikhaliyev, Namig G.'
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld surface analysis of
 5-oxo-N-phenyl-3-(thiophen-2-yl)-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxamide
;
_journal_coeditor_code           WM5747
_journal_issue                   2
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S205698902500057X
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C23 H19 N O2 S'
_chemical_formula_moiety         'C23 H19 N O2 S'
_chemical_formula_sum            'C23 H19 N O2 S'
_chemical_formula_weight         373.45
_chemical_name_systematic
5-Oxo-N-phenyl-3-(thiophen-2-yl)-2,3,4,5-tetrahydro-[1,1'-biphenyl]-4-carboxamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 107.4160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.1416(5)
_cell_length_b                   12.8991(4)
_cell_length_c                   19.0656(5)
_cell_measurement_reflns_used    9482
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.46
_cell_measurement_theta_min      2.24
_cell_volume                     3787.71(19)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            44070
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.589
_diffrn_reflns_theta_min         2.147
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       prism
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.647
_refine_ls_abs_structure_details
;
Refined as an inversion twin;
Flack x determined using 5763 quotients
[(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
;
_refine_ls_abs_structure_Flack   0.37(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         13781
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0623P)²+3.9600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                12646
_reflns_number_total             13781
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5747.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2023363
_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   0.954
_shelx_estimated_absorpt_t_max   0.972
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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.73160(7) 0.42886(8) 0.71887(6) 0.02445(19) Uani d 0.7 A 1
S S1' 0.73378(16) 0.38641(19) 0.57558(16) 0.0263(5) Uani d 0.3 A 2
O O1 0.40433(13) 0.60901(15) 0.57901(13) 0.0270(4) Uani d 1 . .
O O2 0.49029(13) 0.39952(15) 0.53972(10) 0.0221(3) Uani d 1 . .
N N1 0.48998(14) 0.37371(15) 0.65812(11) 0.0165(3) Uani d 1 . .
C C1 0.48285(15) 0.62230(18) 0.59522(13) 0.0173(4) Uani d 1 . .
C C2 0.54702(15) 0.53526(17) 0.62719(13) 0.0163(4) Uani d 1 . .
H H2 0.564164 0.539595 0.682040 0.020 Uiso calc 1 . .
C C3 0.62924(13) 0.54764(17) 0.60251(13) 0.0174(4) Uani d 1 . .
H H3 0.610628 0.545920 0.547561 0.021 Uiso calc 1 . .
C C4 0.66919(15) 0.65469(18) 0.62661(15) 0.0208(4) Uani d 1 . .
H H4A 0.693229 0.655867 0.680852 0.025 Uiso calc 1 . .
H H4B 0.717865 0.665911 0.605888 0.025 Uiso calc 1 . .
C C5 0.60495(15) 0.74233(17) 0.60257(13) 0.0162(4) Uani d 1 . .
C C6 0.51878(15) 0.72339(17) 0.58679(13) 0.0168(4) Uani d 1 . .
H H6 0.479630 0.779177 0.569254 0.020 Uiso calc 1 . .
C C7 0.50540(14) 0.42931(17) 0.60344(13) 0.0155(4) Uani d 1 . .
C C8 0.46246(15) 0.26899(17) 0.65529(13) 0.0159(4) Uani d 1 . .
C C9 0.47950(19) 0.21882(19) 0.72294(14) 0.0232(5) Uani d 1 . .
H H9 0.508457 0.254912 0.766873 0.028 Uiso calc 1 . .
C C10 0.4544(2) 0.1165(2) 0.72647(16) 0.0263(5) Uani d 1 . .
H H10 0.466516 0.082856 0.772774 0.032 Uiso calc 1 . .
C C11 0.41199(17) 0.06340(19) 0.66302(15) 0.0218(4) Uani d 1 . .
H H11 0.394683 -0.006549 0.665548 0.026 Uiso calc 1 . .
C C12 0.39466(18) 0.1132(2) 0.59509(15) 0.0232(5) Uani d 1 . .
H H12 0.365616 0.076614 0.551390 0.028 Uiso calc 1 . .
C C13 0.41951(16) 0.21586(19) 0.59071(14) 0.0198(4) Uani d 1 . .
H H13 0.407405 0.249391 0.544372 0.024 Uiso calc 1 . .
C C14 0.69198(9) 0.46161(14) 0.62909(10) 0.0199(4) Uani d 1 . .
C C15 0.7246(2) 0.3998(3) 0.5853(3) 0.02445(19) Uani d 0.7 A 1
H H15 0.709503 0.406978 0.533395 0.029 Uiso calc 0.7 A 1
C C16 0.7843(2) 0.3228(3) 0.62621(18) 0.02445(19) Uani d 0.7 A 1
H H16 0.813366 0.273307 0.605154 0.029 Uiso calc 0.7 A 1
C C17 0.79315(18) 0.3309(2) 0.69932(19) 0.02445(19) Uani d 0.7 A 1
H H17 0.829553 0.286942 0.735642 0.029 Uiso calc 0.7 A 1
C C15' 0.7301(4) 0.4225(5) 0.6987(3) 0.0263(5) Uani d 0.3 A 2
H H15A 0.715137 0.454323 0.738197 0.032 Uiso calc 0.3 A 2
C C16' 0.7904(4) 0.3381(5) 0.7164(4) 0.0263(5) Uani d 0.3 A 2
H H16A 0.819170 0.307482 0.762600 0.032 Uiso calc 0.3 A 2
C C17' 0.7948(3) 0.3143(5) 0.6480(3) 0.0263(5) Uani d 0.3 A 2
H H17A 0.830639 0.259395 0.640767 0.032 Uiso calc 0.3 A 2
C C18 0.63757(16) 0.84809(18) 0.59696(13) 0.0179(4) Uani d 1 . .
C C19 0.58505(17) 0.9349(2) 0.59560(17) 0.0252(5) Uani d 1 . .
H H19 0.528169 0.925720 0.599421 0.030 Uiso calc 1 . .
C C20 0.6148(2) 1.0343(2) 0.58875(19) 0.0313(6) Uani d 1 . .
H H20 0.578244 1.092451 0.587643 0.038 Uiso calc 1 . .
C C21 0.6980(2) 1.0486(2) 0.58352(17) 0.0304(6) Uani d 1 . .
H H21 0.718368 1.116423 0.578379 0.037 Uiso calc 1 . .
C C22 0.75120(19) 0.9639(2) 0.58582(18) 0.0300(6) Uani d 1 . .
H H22 0.808301 0.973681 0.582633 0.036 Uiso calc 1 . .
C C23 0.72128(18) 0.8642(2) 0.59279(17) 0.0251(5) Uani d 1 . .
H H23 0.758482 0.806550 0.594727 0.030 Uiso calc 1 . .
S S2 0.28115(7) 0.47394(8) 0.41495(7) 0.02627(18) Uani d 0.7 B 1
S S2' 0.25927(18) 0.4669(2) 0.26876(14) 0.0280(5) Uani d 0.3 B 2
O O3 0.59672(12) 0.67727(16) 0.42626(12) 0.0250(4) Uani d 1 . .
O O4 0.50311(13) 0.52390(14) 0.29766(10) 0.0215(3) Uani d 1 . .
N N2 0.50923(14) 0.41810(15) 0.39523(11) 0.0163(3) Uani d 1 . .
C C24 0.51761(15) 0.68815(19) 0.41100(13) 0.0178(4) Uani d 1 . .
C C25 0.45807(15) 0.59458(17) 0.39697(13) 0.0163(4) Uani d 1 . .
H H25 0.455743 0.567333 0.445444 0.020 Uiso calc 1 . .
C C26 0.36501(13) 0.62122(17) 0.35019(13) 0.0181(4) Uani d 1 . .
H H26 0.366513 0.639001 0.299534 0.022 Uiso calc 1 . .
C C27 0.33101(16) 0.71636(19) 0.38174(15) 0.0204(4) Uani d 1 . .
H H27A 0.275071 0.738234 0.346700 0.024 Uiso calc 1 . .
H H27B 0.319819 0.696322 0.428205 0.024 Uiso calc 1 . .
C C28 0.39277(15) 0.80691(18) 0.39644(13) 0.0166(4) Uani d 1 . .
C C29 0.47893(15) 0.79046(18) 0.40955(13) 0.0177(4) Uani d 1 . .
H H29 0.516314 0.849028 0.418306 0.021 Uiso calc 1 . .
C C30 0.49336(15) 0.50904(17) 0.35838(13) 0.0165(4) Uani d 1 . .
C C31 0.53480(14) 0.32350(17) 0.36947(13) 0.0153(4) Uani d 1 . .
C C32 0.57754(16) 0.25144(18) 0.42214(14) 0.0188(4) Uani d 1 . .
H H32 0.589395 0.267025 0.472893 0.023 Uiso calc 1 . .
C C33 0.60284(17) 0.15704(19) 0.40074(15) 0.0221(4) Uani d 1 . .
H H33 0.632745 0.108574 0.437023 0.026 Uiso calc 1 . .
C C34 0.58502(18) 0.13252(19) 0.32701(16) 0.0238(5) Uani d 1 . .
H H34 0.603118 0.067987 0.312537 0.029 Uiso calc 1 . .
C C35 0.5403(2) 0.2036(2) 0.27440(15) 0.0267(5) Uani d 1 . .
H H35 0.526614 0.186576 0.223729 0.032 Uiso calc 1 . .
C C36 0.51516(19) 0.29968(19) 0.29508(14) 0.0226(5) Uani d 1 . .
H H36 0.485079 0.348121 0.258852 0.027 Uiso calc 1 . .
C C37 0.30635(9) 0.53143(15) 0.34455(11) 0.0236(5) Uani d 1 . .
C C38 0.2622(2) 0.4790(3) 0.2804(3) 0.02627(18) Uani d 0.7 B 1
H H38 0.267720 0.498578 0.233975 0.032 Uiso calc 0.7 B 1
C C39 0.2081(2) 0.3941(3) 0.2878(2) 0.02627(18) Uani d 0.7 B 1
H H39 0.174131 0.351909 0.248964 0.032 Uiso calc 0.7 B 1
C C40 0.21388(18) 0.3843(2) 0.36005(19) 0.02627(18) Uani d 0.7 B 1
H H40 0.183584 0.332886 0.378302 0.032 Uiso calc 0.7 B 1
C C38' 0.2831(4) 0.4893(5) 0.4023(4) 0.0280(5) Uani d 0.3 B 2
H H38A 0.304677 0.517381 0.450437 0.034 Uiso calc 0.3 B 2
C C39' 0.2257(4) 0.4022(5) 0.3880(4) 0.0280(5) Uani d 0.3 B 2
H H39A 0.204087 0.365049 0.421800 0.034 Uiso calc 0.3 B 2
C C40' 0.2093(3) 0.3847(4) 0.3147(3) 0.0280(5) Uani d 0.3 B 2
H H40A 0.172328 0.330200 0.290280 0.034 Uiso calc 0.3 B 2
C C41 0.35706(15) 0.91145(18) 0.39858(13) 0.0175(4) Uani d 1 . .
C C42 0.27141(16) 0.92410(19) 0.40067(15) 0.0211(4) Uani d 1 . .
H H42 0.236348 0.864781 0.400146 0.025 Uiso calc 1 . .
C C43 0.23728(17) 1.0228(2) 0.40349(16) 0.0234(5) Uani d 1 . .
H H43 0.179575 1.030114 0.405746 0.028 Uiso calc 1 . .
C C44 0.28699(18) 1.1103(2) 0.40302(15) 0.0241(5) Uani d 1 . .
H H44 0.263395 1.177438 0.404512 0.029 Uiso calc 1 . .
C C45 0.37189(18) 1.0989(2) 0.40036(15) 0.0230(4) Uani d 1 . .
H H45 0.406196 1.158652 0.399970 0.028 Uiso calc 1 . .
C C46 0.40657(16) 1.00110(19) 0.39827(14) 0.0202(4) Uani d 1 . .
H H46 0.464568 0.994496 0.396597 0.024 Uiso calc 1 . .
H H1N 0.498(2) 0.406(3) 0.699(2) 0.024 Uiso d 1 . .
H H2N 0.496(2) 0.419(3) 0.440(2) 0.024 Uiso d 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 S1 C17 . . 91.85(14) ?
C14 S1' C17' . . 93.6(3) ?
C7 N1 C8 . . 127.3(2) ?
C7 N1 H1N . . 115(3) ?
C8 N1 H1N . . 118(3) ?
O1 C1 C6 . . 121.0(2) ?
O1 C1 C2 . . 121.7(2) ?
C6 C1 C2 . . 117.26(19) ?
C1 C2 C7 . . 110.71(19) ?
C1 C2 C3 . . 110.18(18) ?
C7 C2 C3 . . 110.10(18) ?
C1 C2 H2 . . 108.6 ?
C7 C2 H2 . . 108.6 ?
C3 C2 H2 . . 108.6 ?
C14 C3 C4 . . 112.79(15) ?
C14 C3 C2 . . 112.29(16) ?
C4 C3 C2 . . 108.93(19) ?
C14 C3 H3 . . 107.5 ?
C4 C3 H3 . . 107.5 ?
C2 C3 H3 . . 107.5 ?
C5 C4 C3 . . 113.19(19) ?
C5 C4 H4A . . 108.9 ?
C3 C4 H4A . . 108.9 ?
C5 C4 H4B . . 108.9 ?
C3 C4 H4B . . 108.9 ?
H4A C4 H4B . . 107.8 ?
C6 C5 C18 . . 121.0(2) ?
C6 C5 C4 . . 119.9(2) ?
C18 C5 C4 . . 119.08(19) ?
C5 C6 C1 . . 123.6(2) ?
C5 C6 H6 . . 118.2 ?
C1 C6 H6 . . 118.2 ?
O2 C7 N1 . . 124.8(2) ?
O2 C7 C2 . . 120.8(2) ?
N1 C7 C2 . . 114.36(19) ?
C9 C8 C13 . . 119.7(2) ?
C9 C8 N1 . . 115.7(2) ?
C13 C8 N1 . . 124.6(2) ?
C10 C9 C8 . . 120.4(2) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C11 C10 C9 . . 120.3(2) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C10 C11 C12 . . 119.6(2) ?
C10 C11 H11 . . 120.2 ?
C12 C11 H11 . . 120.2 ?
C13 C12 C11 . . 120.7(2) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C12 C13 C8 . . 119.3(2) ?
C12 C13 H13 . . 120.4 ?
C8 C13 H13 . . 120.4 ?
C15 C14 C3 . . 125.1(3) ?
C15' C14 C3 . . 131.5(4) ?
C15' C14 S1' . . 103.1(4) ?
C3 C14 S1' . . 125.3(2) ?
C15 C14 S1 . . 112.0(3) ?
C3 C14 S1 . . 122.98(16) ?
C14 C15 C16 . . 112.8(4) ?
C14 C15 H15 . . 123.6 ?
C16 C15 H15 . . 123.6 ?
C17 C16 C15 . . 110.5(4) ?
C17 C16 H16 . . 124.7 ?
C15 C16 H16 . . 124.7 ?
C16 C17 S1 . . 112.8(3) ?
C16 C17 H17 . . 123.6 ?
S1 C17 H17 . . 123.6 ?
C14 C15' C16' . . 125.5(8) ?
C14 C15' H15A . . 117.3 ?
C16' C15' H15A . . 117.3 ?
C17' C16' C15' . . 99.9(8) ?
C17' C16' H16A . . 130.0 ?
C15' C16' H16A . . 130.0 ?
C16' C17' S1' . . 117.9(7) ?
C16' C17' H17A . . 121.1 ?
S1' C17' H17A . . 121.1 ?
C23 C18 C19 . . 118.1(2) ?
C23 C18 C5 . . 121.0(2) ?
C19 C18 C5 . . 120.9(2) ?
C20 C19 C18 . . 121.1(3) ?
C20 C19 H19 . . 119.5 ?
C18 C19 H19 . . 119.5 ?
C19 C20 C21 . . 119.8(3) ?
C19 C20 H20 . . 120.1 ?
C21 C20 H20 . . 120.1 ?
C22 C21 C20 . . 119.9(2) ?
C22 C21 H21 . . 120.1 ?
C20 C21 H21 . . 120.1 ?
C21 C22 C23 . . 120.2(3) ?
C21 C22 H22 . . 119.9 ?
C23 C22 H22 . . 119.9 ?
C18 C23 C22 . . 120.9(3) ?
C18 C23 H23 . . 119.6 ?
C22 C23 H23 . . 119.6 ?
C37 S2 C40 . . 94.03(16) ?
C37 S2' C40' . . 91.6(3) ?
C30 N2 C31 . . 126.5(2) ?
C30 N2 H2N . . 114(2) ?
C31 N2 H2N . . 119(2) ?
O3 C24 C29 . . 121.1(2) ?
O3 C24 C25 . . 120.6(2) ?
C29 C24 C25 . . 118.20(19) ?
C24 C25 C30 . . 110.62(18) ?
C24 C25 C26 . . 112.44(18) ?
C30 C25 C26 . . 108.80(19) ?
C24 C25 H25 . . 108.3 ?
C30 C25 H25 . . 108.3 ?
C26 C25 H25 . . 108.3 ?
C37 C26 C27 . . 110.94(16) ?
C37 C26 C25 . . 111.09(15) ?
C27 C26 C25 . . 110.6(2) ?
C37 C26 H26 . . 108.0 ?
C27 C26 H26 . . 108.0 ?
C25 C26 H26 . . 108.0 ?
C28 C27 C26 . . 113.43(19) ?
C28 C27 H27A . . 108.9 ?
C26 C27 H27A . . 108.9 ?
C28 C27 H27B . . 108.9 ?
C26 C27 H27B . . 108.9 ?
H27A C27 H27B . . 107.7 ?
C29 C28 C41 . . 121.8(2) ?
C29 C28 C27 . . 119.9(2) ?
C41 C28 C27 . . 118.21(19) ?
C28 C29 C24 . . 123.8(2) ?
C28 C29 H29 . . 118.1 ?
C24 C29 H29 . . 118.1 ?
O4 C30 N2 . . 124.5(2) ?
O4 C30 C25 . . 120.8(2) ?
N2 C30 C25 . . 114.6(2) ?
C32 C31 C36 . . 120.0(2) ?
C32 C31 N2 . . 117.2(2) ?
C36 C31 N2 . . 122.7(2) ?
C33 C32 C31 . . 120.1(2) ?
C33 C32 H32 . . 119.9 ?
C31 C32 H32 . . 119.9 ?
C32 C33 C34 . . 120.7(2) ?
C32 C33 H33 . . 119.7 ?
C34 C33 H33 . . 119.7 ?
C33 C34 C35 . . 119.1(2) ?
C33 C34 H34 . . 120.4 ?
C35 C34 H34 . . 120.4 ?
C34 C35 C36 . . 120.9(2) ?
C34 C35 H35 . . 119.6 ?
C36 C35 H35 . . 119.6 ?
C31 C36 C35 . . 119.1(2) ?
C31 C36 H36 . . 120.4 ?
C35 C36 H36 . . 120.4 ?
C38' C37 C26 . . 124.9(4) ?
C38 C37 C26 . . 126.3(3) ?
C38' C37 S2' . . 109.8(4) ?
C26 C37 S2' . . 125.3(2) ?
C38 C37 S2 . . 107.7(3) ?
C26 C37 S2 . . 126.02(18) ?
C37 C38 C39 . . 116.8(4) ?
C37 C38 H38 . . 121.6 ?
C39 C38 H38 . . 121.6 ?
C40 C39 C38 . . 108.2(4) ?
C40 C39 H39 . . 125.9 ?
C38 C39 H39 . . 125.9 ?
C39 C40 S2 . . 113.3(3) ?
C39 C40 H40 . . 123.3 ?
S2 C40 H40 . . 123.3 ?
C37 C38' C39' . . 118.2(7) ?
C37 C38' H38A . . 120.9 ?
C39' C38' H38A . . 120.9 ?
C40' C39' C38' . . 104.0(8) ?
C40' C39' H39A . . 128.0 ?
C38' C39' H39A . . 128.0 ?
C39' C40' S2' . . 116.4(6) ?
C39' C40' H40A . . 121.8 ?
S2' C40' H40A . . 121.8 ?
C42 C41 C46 . . 118.0(2) ?
C42 C41 C28 . . 120.3(2) ?
C46 C41 C28 . . 121.7(2) ?
C43 C42 C41 . . 120.7(2) ?
C43 C42 H42 . . 119.6 ?
C41 C42 H42 . . 119.6 ?
C44 C43 C42 . . 120.5(2) ?
C44 C43 H43 . . 119.8 ?
C42 C43 H43 . . 119.8 ?
C43 C44 C45 . . 119.5(2) ?
C43 C44 H44 . . 120.3 ?
C45 C44 H44 . . 120.3 ?
C46 C45 C44 . . 120.4(2) ?
C46 C45 H45 . . 119.8 ?
C44 C45 H45 . . 119.8 ?
C45 C46 C41 . . 120.9(2) ?
C45 C46 H46 . . 119.6 ?
C41 C46 H46 . . 119.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C14 . 1.692(2) ?
S1 C17 . 1.716(3) ?
S1' C14 . 1.688(3) ?
S1' C17' . 1.712(4) ?
O1 C1 . 1.223(3) ?
O2 C7 . 1.227(3) ?
N1 C7 . 1.349(3) ?
N1 C8 . 1.418(3) ?
N1 H1N . 0.85(4) ?
C1 C6 . 1.455(3) ?
C1 C2 . 1.526(3) ?
C2 C7 . 1.530(3) ?
C2 C3 . 1.543(3) ?
C2 H2 . 1.0000 ?
C3 C14 . 1.486(3) ?
C3 C4 . 1.535(3) ?
C3 H3 . 1.0000 ?
C4 C5 . 1.510(3) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.354(3) ?
C5 C18 . 1.478(3) ?
C6 H6 . 0.9500 ?
C8 C9 . 1.395(3) ?
C8 C13 . 1.398(3) ?
C9 C10 . 1.388(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.380(4) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.397(4) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.394(3) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 C15 . 1.369(4) ?
C14 C15' . 1.381(4) ?
C15 C16 . 1.440(4) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.362(3) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
C15' C16' . 1.432(4) ?
C15' H15A . 0.9500 ?
C16' C17' . 1.361(4) ?
C16' H16A . 0.9500 ?
C17' H17A . 0.9500 ?
C18 C23 . 1.393(3) ?
C18 C19 . 1.401(4) ?
C19 C20 . 1.389(4) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.389(4) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.381(5) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.394(4) ?
C22 H22 . 0.9500 ?
C23 H23 . 0.9500 ?
S2 C37 . 1.686(2) ?
S2 C40 . 1.712(3) ?
S2' C37 . 1.644(3) ?
S2' C40' . 1.722(4) ?
O3 C24 . 1.230(3) ?
O4 C30 . 1.229(3) ?
N2 C30 . 1.352(3) ?
N2 C31 . 1.422(3) ?
N2 H2N . 0.94(4) ?
C24 C29 . 1.457(3) ?
C24 C25 . 1.516(3) ?
C25 C30 . 1.528(3) ?
C25 C26 . 1.539(3) ?
C25 H25 . 1.0000 ?
C26 C37 . 1.479(3) ?
C26 C27 . 1.538(3) ?
C26 H26 . 1.0000 ?
C27 C28 . 1.507(3) ?
C27 H27A . 0.9900 ?
C27 H27B . 0.9900 ?
C28 C29 . 1.354(3) ?
C28 C41 . 1.472(3) ?
C29 H29 . 0.9500 ?
C31 C32 . 1.391(3) ?
C31 C36 . 1.392(3) ?
C32 C33 . 1.384(3) ?
C32 H32 . 0.9500 ?
C33 C34 . 1.385(4) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.391(4) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.397(4) ?
C35 H35 . 0.9500 ?
C36 H36 . 0.9500 ?
C37 C38' . 1.377(4) ?
C37 C38 . 1.392(4) ?
C38 C39 . 1.435(4) ?
C38 H38 . 0.9500 ?
C39 C40 . 1.358(3) ?
C39 H39 . 0.9500 ?
C40 H40 . 0.9500 ?
C38' C39' . 1.430(4) ?
C38' H38A . 0.9500 ?
C39' C40' . 1.360(4) ?
C39' H39A . 0.9500 ?
C40' H40A . 0.9500 ?
C41 C42 . 1.404(3) ?
C41 C46 . 1.407(3) ?
C42 C43 . 1.395(3) ?
C42 H42 . 0.9500 ?
C43 C44 . 1.386(4) ?
C43 H43 . 0.9500 ?
C44 C45 . 1.394(4) ?
C44 H44 . 0.9500 ?
C45 C46 . 1.386(3) ?
C45 H45 . 0.9500 ?
C46 H46 . 0.9500 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 H2 2.95 . . yes
S2 H25 2.96 . . yes
S2 H27B 2.93 . . yes
O2 C13 2.920(3) . . yes
O4 C36 2.900(3) . . yes
H16 O1 2.71 . 3_545 yes
H17A O1 2.72 . 3_545 yes
H22 O1 2.35 . 3_555 yes
O2 H3 2.68 . . yes
O2 H13 2.37 . . yes
O2 H2N 1.95(4) . . yes
O3 H43 2.42 . 3_545 yes
O4 H26 2.67 . . yes
O4 H36 2.38 . . yes
H1N O4 2.07(4) . 2_565 yes
C4 H23 2.61 . . yes
C6 H19 2.62 . . yes
C7 H13 2.84 . . yes
C19 H6 2.58 . . yes
C23 H4B 2.57 . . yes
C27 H42 2.54 . . yes
C27 H38A 2.97 . . yes
C29 H46 2.65 . . yes
C30 H36 2.79 . . yes
C30 H43 2.88 . 3_545 yes
C40 H44 2.84 . 1_545 yes
C42 H27A 2.61 . . yes
C46 H29 2.59 . . yes
H1N H9 2.32 . . yes
H1N H2 2.10 . . yes
H2N H25 2.03 . . yes
H4B H23 1.96 . . yes
H6 H19 2.06 . . yes
H27A H42 2.11 . . yes
H27B H38A 2.37 . . yes
H29 H46 2.05 . . yes
H40 H44 2.36 . 1_545 yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N O4 2_565 0.85(4) 2.07(4) 2.921(3) 173(4) yes
N2 H2N O2 . 0.94(4) 1.95(4) 2.871(3) 167(3) yes
C11 H11 Cg1 3_455 0.95 2.71 3.468(3) 137 yes
C12 H12 Cg10 2_574 0.95 2.87 3.772(3) 159 yes
C34 H34 Cg2 3_545 0.95 2.78 3.546(3) 139 yes
C38 H38 Cg7 3_455 0.95 2.81 3.603(5) 142 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C7 . . . . 25.9(3) ?
C6 C1 C2 C7 . . . . -156.0(2) ?
O1 C1 C2 C3 . . . . 147.9(2) ?
C6 C1 C2 C3 . . . . -34.0(3) ?
C1 C2 C3 C14 . . . . -177.06(17) ?
C7 C2 C3 C14 . . . . -54.7(2) ?
C1 C2 C3 C4 . . . . 57.3(2) ?
C7 C2 C3 C4 . . . . 179.64(19) ?
C14 C3 C4 C5 . . . . -177.59(19) ?
C2 C3 C4 C5 . . . . -52.2(3) ?
C3 C4 C5 C6 . . . . 22.4(3) ?
C3 C4 C5 C18 . . . . -157.9(2) ?
C18 C5 C6 C1 . . . . -176.4(2) ?
C4 C5 C6 C1 . . . . 3.3(4) ?
O1 C1 C6 C5 . . . . -178.8(2) ?
C2 C1 C6 C5 . . . . 3.1(3) ?
C8 N1 C7 O2 . . . . 6.8(4) ?
C8 N1 C7 C2 . . . . -171.5(2) ?
C1 C2 C7 O2 . . . . 71.4(3) ?
C3 C2 C7 O2 . . . . -50.7(3) ?
C1 C2 C7 N1 . . . . -110.2(2) ?
C3 C2 C7 N1 . . . . 127.7(2) ?
C7 N1 C8 C9 . . . . 158.7(2) ?
C7 N1 C8 C13 . . . . -22.4(4) ?
C13 C8 C9 C10 . . . . 0.3(4) ?
N1 C8 C9 C10 . . . . 179.3(2) ?
C8 C9 C10 C11 . . . . -0.3(4) ?
C9 C10 C11 C12 . . . . 0.2(4) ?
C10 C11 C12 C13 . . . . -0.2(4) ?
C11 C12 C13 C8 . . . . 0.2(4) ?
C9 C8 C13 C12 . . . . -0.2(4) ?
N1 C8 C13 C12 . . . . -179.2(2) ?
C4 C3 C14 C15 . . . . -111.8(2) ?
C2 C3 C14 C15 . . . . 124.67(19) ?
C4 C3 C14 C15' . . . . 69.4(2) ?
C2 C3 C14 C15' . . . . -54.2(2) ?
C4 C3 C14 S1' . . . . -110.7(2) ?
C2 C3 C14 S1' . . . . 125.8(2) ?
C4 C3 C14 S1 . . . . 68.23(18) ?
C2 C3 C14 S1 . . . . -55.32(17) ?
C17' S1' C14 C15' . . . . -0.03(12) ?
C17' S1' C14 C3 . . . . -179.97(7) ?
C17 S1 C14 C15 . . . . -0.02(11) ?
C17 S1 C14 C3 . . . . 179.97(6) ?
C3 C14 C15 C16 . . . . 179.94(10) ?
S1 C14 C15 C16 . . . . -0.07(18) ?
C14 C15 C16 C17 . . . . 0.1(2) ?
C15 C16 C17 S1 . . . . -0.2(2) ?
C14 S1 C17 C16 . . . . 0.11(14) ?
C3 C14 C15' C16' . . . . -179.92(14) ?
S1' C14 C15' C16' . . . . 0.2(2) ?
C14 C15' C16' C17' . . . . -0.2(3) ?
C15' C16' C17' S1' . . . . 0.2(2) ?
C14 S1' C17' C16' . . . . -0.08(17) ?
C6 C5 C18 C23 . . . . -161.9(2) ?
C4 C5 C18 C23 . . . . 18.4(3) ?
C6 C5 C18 C19 . . . . 18.0(4) ?
C4 C5 C18 C19 . . . . -161.7(2) ?
C23 C18 C19 C20 . . . . 1.3(4) ?
C5 C18 C19 C20 . . . . -178.6(3) ?
C18 C19 C20 C21 . . . . -0.3(5) ?
C19 C20 C21 C22 . . . . -0.6(5) ?
C20 C21 C22 C23 . . . . 0.5(5) ?
C19 C18 C23 C22 . . . . -1.4(4) ?
C5 C18 C23 C22 . . . . 178.5(3) ?
C21 C22 C23 C18 . . . . 0.5(5) ?
O3 C24 C25 C30 . . . . -35.2(3) ?
C29 C24 C25 C30 . . . . 147.8(2) ?
O3 C24 C25 C26 . . . . -157.1(2) ?
C29 C24 C25 C26 . . . . 26.0(3) ?
C24 C25 C26 C37 . . . . -173.58(18) ?
C30 C25 C26 C37 . . . . 63.5(2) ?
C24 C25 C26 C27 . . . . -49.9(3) ?
C30 C25 C26 C27 . . . . -172.79(19) ?
C37 C26 C27 C28 . . . . 173.80(19) ?
C25 C26 C27 C28 . . . . 50.0(3) ?
C26 C27 C28 C29 . . . . -25.5(3) ?
C26 C27 C28 C41 . . . . 156.6(2) ?
C41 C28 C29 C24 . . . . 177.4(2) ?
C27 C28 C29 C24 . . . . -0.4(4) ?
O3 C24 C29 C28 . . . . -176.9(2) ?
C25 C24 C29 C28 . . . . 0.1(3) ?
C31 N2 C30 O4 . . . . -3.7(4) ?
C31 N2 C30 C25 . . . . 174.1(2) ?
C24 C25 C30 O4 . . . . -60.9(3) ?
C26 C25 C30 O4 . . . . 63.1(3) ?
C24 C25 C30 N2 . . . . 121.2(2) ?
C26 C25 C30 N2 . . . . -114.8(2) ?
C30 N2 C31 C32 . . . . 157.3(2) ?
C30 N2 C31 C36 . . . . -25.8(4) ?
C36 C31 C32 C33 . . . . 1.8(4) ?
N2 C31 C32 C33 . . . . 178.9(2) ?
C31 C32 C33 C34 . . . . -0.9(4) ?
C32 C33 C34 C35 . . . . -0.8(4) ?
C33 C34 C35 C36 . . . . 1.5(4) ?
C32 C31 C36 C35 . . . . -1.1(4) ?
N2 C31 C36 C35 . . . . -178.0(2) ?
C34 C35 C36 C31 . . . . -0.6(4) ?
C27 C26 C37 C38' . . . . -57.0(2) ?
C25 C26 C37 C38' . . . . 66.5(2) ?
C27 C26 C37 C38 . . . . 119.5(2) ?
C25 C26 C37 C38 . . . . -117.0(2) ?
C27 C26 C37 S2' . . . . 123.1(2) ?
C25 C26 C37 S2' . . . . -113.4(2) ?
C27 C26 C37 S2 . . . . -60.68(18) ?
C25 C26 C37 S2 . . . . 62.81(17) ?
C40' S2' C37 C38' . . . . 0.00(12) ?
C40' S2' C37 C26 . . . . 179.91(7) ?
C40 S2 C37 C38 . . . . -0.36(11) ?
C40 S2 C37 C26 . . . . 179.79(7) ?
C26 C37 C38 C39 . . . . -179.62(11) ?
S2 C37 C38 C39 . . . . 0.54(18) ?
C37 C38 C39 C40 . . . . -0.5(2) ?
C38 C39 C40 S2 . . . . 0.2(2) ?
C37 S2 C40 C39 . . . . 0.12(15) ?
C26 C37 C38' C39' . . . . -179.91(13) ?
S2' C37 C38' C39' . . . . 0.0(2) ?
C37 C38' C39' C40' . . . . 0.0(3) ?
C38' C39' C40' S2' . . . . 0.0(2) ?
C37 S2' C40' C39' . . . . 0.00(17) ?
C29 C28 C41 C42 . . . . -166.2(2) ?
C27 C28 C41 C42 . . . . 11.7(3) ?
C29 C28 C41 C46 . . . . 14.1(4) ?
C27 C28 C41 C46 . . . . -168.0(2) ?
C46 C41 C42 C43 . . . . -1.0(4) ?
C28 C41 C42 C43 . . . . 179.3(2) ?
C41 C42 C43 C44 . . . . 1.1(4) ?
C42 C43 C44 C45 . . . . -0.6(4) ?
C43 C44 C45 C46 . . . . -0.1(4) ?
C44 C45 C46 C41 . . . . 0.2(4) ?
C42 C41 C46 C45 . . . . 0.3(4) ?
C28 C41 C46 C45 . . . . -180.0(2) ?
