#------------------------------------------------------------------------------
#$Date: 2022-04-04 02:11:35 +0300 (Mon, 04 Apr 2022) $
#$Revision: 274286 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/67/1566733.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_1566733
loop_
_publ_author_name
'Dong, Jingyue'
'Gao, Wei'
'Li, Kun'
'Hong, Zeyu'
'Tang, Liangfu'
'Han, Lijun'
'Wang, Zhihong'
'Fan, Zhijin'
_publ_section_title
;
 Design, Synthesis, and Biological Evaluation of Novel Psoralen-Based
 1,3,4-Oxadiazoles as Potent Fungicide Candidates Targeting Pyruvate
 Kinase.
;
_journal_issue                   11
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              3435
_journal_page_last               3446
_journal_paper_doi               10.1021/acs.jafc.1c07911
_journal_volume                  70
_journal_year                    2022
_chemical_formula_moiety         'C32 H28 N2 O5 S'
_chemical_formula_sum            'C32 H28 N2 O5 S'
_chemical_formula_weight         552.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                102.141(6)
_cell_angle_beta                 94.257(5)
_cell_angle_gamma                104.092(5)
_cell_formula_units_Z            2
_cell_length_a                   7.2319(4)
_cell_length_b                   11.7336(7)
_cell_length_c                   16.6396(12)
_cell_measurement_reflns_used    6116
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      30.7410
_cell_measurement_theta_min      1.8440
_cell_volume                     1327.08(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    2.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    2.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    2.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0402844000
_diffrn_orient_matrix_UB_12      0.0626585000
_diffrn_orient_matrix_UB_13      0.0174612000
_diffrn_orient_matrix_UB_21      -0.0184247000
_diffrn_orient_matrix_UB_22      0.0122800000
_diffrn_orient_matrix_UB_23      -0.0393407000
_diffrn_orient_matrix_UB_31      -0.0918998000
_diffrn_orient_matrix_UB_32      0.0060820000
_diffrn_orient_matrix_UB_33      0.0090810000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.1094
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20106
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.852
_diffrn_reflns_theta_min         1.841
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0094(15)
_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   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         8855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1357
_refine_ls_R_factor_gt           0.0704
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0595P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1759
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4873
_reflns_number_total             8855
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jf1c07911_si_003.cif
_cod_data_source_block           r20210709a
_cod_database_code               1566733
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_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   0.975
_shelx_estimated_absorpt_t_min   0.965
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C15(H15), C17(H17), C24(H24),
 C25(H25), C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.922
_oxdiff_exptl_absorpt_empirical_full_min 0.688
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
S1 S 0.98597(9) 0.16165(5) 0.05744(4) 0.03335(17) Uani 1 1 d . . . . .
O1 O 1.1071(2) 0.23871(16) 0.13449(11) 0.0410(4) Uani 1 1 d . . . . .
O2 O 0.6821(2) 0.14152(13) 0.14962(9) 0.0291(4) Uani 1 1 d . . . . .
O3 O 0.4691(3) -0.06192(14) 0.32549(11) 0.0441(5) Uani 1 1 d . . . . .
O4 O 0.5946(2) 0.09124(13) 0.43335(10) 0.0318(4) Uani 1 1 d . . . . .
O5 O 0.8415(2) 0.41750(15) 0.67099(9) 0.0339(4) Uani 1 1 d . . . . .
N1 N 0.5119(3) -0.04785(16) 0.09917(12) 0.0327(5) Uani 1 1 d . . . . .
N2 N 0.6726(3) -0.02474(17) 0.05543(12) 0.0348(5) Uani 1 1 d . . . . .
C1 C 0.9769(3) 0.7963(2) 0.66545(15) 0.0364(6) Uani 1 1 d . . . . .
H1 H 1.033606 0.779638 0.713558 0.044 Uiso 1 1 calc R . . . .
C2 C 0.9988(3) 0.9149(2) 0.66066(18) 0.0435(7) Uani 1 1 d . . . . .
H2 H 1.068646 0.978697 0.705769 0.052 Uiso 1 1 calc R . . . .
C3 C 0.9202(3) 0.9417(2) 0.59115(17) 0.0401(6) Uani 1 1 d . . . . .
H3 H 0.937056 1.023399 0.588033 0.048 Uiso 1 1 calc R . . . .
C4 C 0.8167(3) 0.8485(2) 0.52599(15) 0.0349(6) Uani 1 1 d . . . . .
H4 H 0.761543 0.866423 0.478095 0.042 Uiso 1 1 calc R . . . .
C5 C 0.7927(3) 0.7285(2) 0.53017(14) 0.0295(5) Uani 1 1 d . . . . .
H5 H 0.721605 0.665399 0.484895 0.035 Uiso 1 1 calc R . . . .
C6 C 0.8718(3) 0.6995(2) 0.60000(14) 0.0277(5) Uani 1 1 d . . . . .
C7 C 0.8451(3) 0.5733(2) 0.60804(13) 0.0265(5) Uani 1 1 d . . . . .
C8 C 0.7753(3) 0.45885(19) 0.54564(13) 0.0239(4) Uani 1 1 d . . . . .
C9 C 0.7121(3) 0.42283(18) 0.45996(13) 0.0233(4) Uani 1 1 d . . . . .
H9 H 0.712264 0.481753 0.428568 0.028 Uiso 1 1 calc R . . . .
C10 C 0.6488(3) 0.29957(18) 0.42122(13) 0.0222(4) Uani 1 1 d . . . . .
C11 C 0.5629(3) 0.25494(19) 0.33430(13) 0.0230(4) Uani 1 1 d . . . . .
C12 C 0.4935(3) 0.13365(19) 0.30254(14) 0.0250(5) Uani 1 1 d . . . . .
C13 C 0.5156(3) 0.0472(2) 0.35162(15) 0.0300(5) Uani 1 1 d . . . . .
C14 C 0.6547(3) 0.21363(19) 0.46883(14) 0.0263(5) Uani 1 1 d . . . . .
C15 C 0.7176(3) 0.2455(2) 0.55279(14) 0.0293(5) Uani 1 1 d . . . . .
H15 H 0.720295 0.186752 0.584075 0.035 Uiso 1 1 calc R . . . .
C16 C 0.7762(3) 0.3678(2) 0.58855(14) 0.0282(5) Uani 1 1 d . . . . .
C17 C 0.8795(3) 0.5411(2) 0.68050(14) 0.0337(5) Uani 1 1 d . . . . .
H17 H 0.925041 0.597763 0.732253 0.040 Uiso 1 1 calc R . . . .
C18 C 0.5538(3) 0.34569(19) 0.28318(13) 0.0276(5) Uani 1 1 d . . . . .
H18A H 0.684527 0.390791 0.279043 0.041 Uiso 1 1 calc GR . . . .
H18B H 0.483703 0.401930 0.309705 0.041 Uiso 1 1 calc GR . . . .
H18C H 0.487071 0.303401 0.227516 0.041 Uiso 1 1 calc GR . . . .
C19 C 0.3911(3) 0.07675(19) 0.21460(14) 0.0286(5) Uani 1 1 d . . . . .
H19A H 0.295361 0.000354 0.214494 0.034 Uiso 1 1 calc R . . . .
H19B H 0.320664 0.131971 0.197278 0.034 Uiso 1 1 calc R . . . .
C20 C 0.5232(3) 0.05090(18) 0.15331(13) 0.0256(5) Uani 1 1 d . . . . .
C21 C 0.7636(3) 0.08626(19) 0.08677(13) 0.0266(5) Uani 1 1 d . . . . .
C22 C 0.8934(3) 0.25902(19) 0.00147(14) 0.0283(5) Uani 1 1 d . . . . .
H22A H 0.994279 0.294452 -0.030007 0.034 Uiso 1 1 calc R . . . .
H22B H 0.782091 0.208048 -0.039325 0.034 Uiso 1 1 calc R . . . .
C23 C 0.8317(3) 0.36006(19) 0.05413(13) 0.0251(5) Uani 1 1 d . . . . .
C24 C 0.6383(3) 0.3567(2) 0.05686(13) 0.0278(5) Uani 1 1 d . . . . .
H24 H 0.541745 0.286879 0.027099 0.033 Uiso 1 1 calc R . . . .
C25 C 0.5851(3) 0.45451(19) 0.10278(13) 0.0270(5) Uani 1 1 d . . . . .
H25 H 0.452278 0.450258 0.103230 0.032 Uiso 1 1 calc R . . . .
C26 C 0.7216(3) 0.55898(18) 0.14831(13) 0.0232(4) Uani 1 1 d . . . . .
C27 C 0.9156(3) 0.55959(19) 0.14649(14) 0.0272(5) Uani 1 1 d . . . . .
H27 H 1.012449 0.627739 0.178085 0.033 Uiso 1 1 calc R . . . .
C28 C 0.9695(3) 0.4631(2) 0.09966(13) 0.0273(5) Uani 1 1 d . . . . .
H28 H 1.102132 0.467378 0.098649 0.033 Uiso 1 1 calc R . . . .
C29 C 0.6690(3) 0.66946(19) 0.19802(13) 0.0258(5) Uani 1 1 d . . . . .
C30 C 0.4514(3) 0.6579(2) 0.18457(15) 0.0344(5) Uani 1 1 d . . . . .
H30A H 0.409300 0.647146 0.125462 0.052 Uiso 1 1 calc GR . . . .
H30B H 0.424982 0.731377 0.216188 0.052 Uiso 1 1 calc GR . . . .
H30C H 0.381456 0.587883 0.203508 0.052 Uiso 1 1 calc GR . . . .
C31 C 0.7703(3) 0.7823(2) 0.16948(16) 0.0349(6) Uani 1 1 d . . . . .
H31A H 0.909940 0.795955 0.180471 0.052 Uiso 1 1 calc GR . . . .
H31B H 0.733448 0.852701 0.199851 0.052 Uiso 1 1 calc GR . . . .
H31C H 0.732162 0.770246 0.109894 0.052 Uiso 1 1 calc GR . . . .
C32 C 0.7325(4) 0.6889(2) 0.29114(14) 0.0423(7) Uani 1 1 d . . . . .
H32A H 0.661038 0.620089 0.310871 0.063 Uiso 1 1 calc GR . . . .
H32B H 0.706484 0.763302 0.321410 0.063 Uiso 1 1 calc GR . . . .
H32C H 0.870574 0.695720 0.300557 0.063 Uiso 1 1 calc GR . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C21 106.94(10) . . ?
O1 S1 C22 108.30(10) . . ?
C21 S1 C22 98.12(10) . . ?
C21 O2 C20 102.26(16) . . ?
C13 O4 C14 121.67(17) . . ?
C16 O5 C17 105.79(17) . . ?
C20 N1 N2 106.74(18) . . ?
C21 N2 N1 105.51(18) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C6 121.0(2) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 119.8(2) . . ?
C5 C6 C1 117.4(2) . . ?
C5 C6 C7 122.8(2) . . ?
C8 C7 C6 130.42(19) . . ?
C17 C7 C6 124.6(2) . . ?
C17 C7 C8 104.9(2) . . ?
C9 C8 C7 136.6(2) . . ?
C16 C8 C7 105.68(19) . . ?
C16 C8 C9 117.8(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.55(19) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 122.72(18) . . ?
C9 C10 C14 119.17(19) . . ?
C14 C10 C11 117.95(19) . . ?
C10 C11 C18 118.46(18) . . ?
C12 C11 C10 119.24(19) . . ?
C12 C11 C18 122.30(19) . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 C19 124.04(19) . . ?
C13 C12 C19 114.68(19) . . ?
O3 C13 O4 117.0(2) . . ?
O3 C13 C12 124.7(2) . . ?
O4 C13 C12 118.28(19) . . ?
O4 C14 C10 121.3(2) . . ?
C15 C14 O4 115.79(19) . . ?
C15 C14 C10 122.9(2) . . ?
C14 C15 H15 122.0 . . ?
C14 C15 C16 115.9(2) . . ?
C16 C15 H15 122.0 . . ?
O5 C16 C8 110.6(2) . . ?
O5 C16 C15 124.7(2) . . ?
C15 C16 C8 124.7(2) . . ?
O5 C17 H17 123.5 . . ?
C7 C17 O5 113.0(2) . . ?
C7 C17 H17 123.5 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C12 C19 H19A 108.9 . . ?
C12 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 C12 113.45(18) . . ?
C20 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
O2 C20 C19 119.00(18) . . ?
N1 C20 O2 111.9(2) . . ?
N1 C20 C19 129.1(2) . . ?
O2 C21 S1 121.80(16) . . ?
N2 C21 S1 124.49(18) . . ?
N2 C21 O2 113.57(19) . . ?
S1 C22 H22A 108.4 . . ?
S1 C22 H22B 108.4 . . ?
H22A C22 H22B 107.4 . . ?
C23 C22 S1 115.66(15) . . ?
C23 C22 H22A 108.4 . . ?
C23 C22 H22B 108.4 . . ?
C24 C23 C22 121.88(19) . . ?
C24 C23 C28 118.1(2) . . ?
C28 C23 C22 120.0(2) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.7(2) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 H25 119.0 . . ?
C24 C25 C26 121.9(2) . . ?
C26 C25 H25 119.0 . . ?
C25 C26 C27 116.6(2) . . ?
C25 C26 C29 123.46(19) . . ?
C27 C26 C29 119.91(18) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 C26 121.7(2) . . ?
C28 C27 H27 119.2 . . ?
C23 C28 H28 119.5 . . ?
C27 C28 C23 121.0(2) . . ?
C27 C28 H28 119.5 . . ?
C26 C29 C30 112.34(17) . . ?
C26 C29 C31 109.28(19) . . ?
C26 C29 C32 110.71(18) . . ?
C31 C29 C30 106.92(18) . . ?
C32 C29 C30 108.6(2) . . ?
C32 C29 C31 108.87(18) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
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
S1 O1 1.4793(17) . ?
S1 C21 1.792(2) . ?
S1 C22 1.830(2) . ?
O2 C20 1.377(2) . ?
O2 C21 1.362(3) . ?
O3 C13 1.215(3) . ?
O4 C13 1.374(3) . ?
O4 C14 1.379(3) . ?
O5 C16 1.370(3) . ?
O5 C17 1.381(3) . ?
N1 N2 1.418(3) . ?
N1 C20 1.290(3) . ?
N2 C21 1.283(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.382(4) . ?
C1 C6 1.411(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(3) . ?
C6 C7 1.482(3) . ?
C7 C8 1.463(3) . ?
C7 C17 1.361(3) . ?
C8 C9 1.406(3) . ?
C8 C16 1.405(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.399(3) . ?
C10 C11 1.463(3) . ?
C10 C14 1.414(3) . ?
C11 C12 1.361(3) . ?
C11 C18 1.506(3) . ?
C12 C13 1.459(3) . ?
C12 C19 1.524(3) . ?
C14 C15 1.379(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(3) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.483(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.500(3) . ?
C23 C24 1.394(3) . ?
C23 C28 1.395(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.393(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.400(3) . ?
C26 C27 1.403(3) . ?
C26 C29 1.532(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.389(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.542(3) . ?
C29 C31 1.536(3) . ?
C29 C32 1.536(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
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
S1 C22 C23 C24 -105.9(2) . . . . ?
S1 C22 C23 C28 76.6(2) . . . . ?
O1 S1 C21 O2 35.9(2) . . . . ?
O1 S1 C21 N2 -139.58(19) . . . . ?
O1 S1 C22 C23 -40.18(19) . . . . ?
O4 C14 C15 C16 -179.47(19) . . . . ?
N1 N2 C21 S1 177.09(15) . . . . ?
N1 N2 C21 O2 1.2(2) . . . . ?
N2 N1 C20 O2 0.2(2) . . . . ?
N2 N1 C20 C19 179.4(2) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C1 C6 C7 C8 -167.4(2) . . . . ?
C1 C6 C7 C17 14.3(3) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C1 C6 C7 -177.9(2) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 C7 178.2(2) . . . . ?
C5 C6 C7 C8 14.2(4) . . . . ?
C5 C6 C7 C17 -164.1(2) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C6 C7 C8 C16 -178.8(2) . . . . ?
C6 C7 C17 O5 179.47(19) . . . . ?
C7 C8 C9 C10 -178.0(2) . . . . ?
C7 C8 C16 O5 -0.4(2) . . . . ?
C7 C8 C16 C15 179.0(2) . . . . ?
C8 C7 C17 O5 0.8(2) . . . . ?
C8 C9 C10 C11 173.67(19) . . . . ?
C8 C9 C10 C14 -1.7(3) . . . . ?
C9 C8 C16 O5 179.95(18) . . . . ?
C9 C8 C16 C15 -0.7(3) . . . . ?
C9 C10 C11 C12 -175.76(19) . . . . ?
C9 C10 C11 C18 3.9(3) . . . . ?
C9 C10 C14 O4 -179.75(19) . . . . ?
C9 C10 C14 C15 1.1(3) . . . . ?
C10 C11 C12 C13 -4.5(3) . . . . ?
C10 C11 C12 C19 176.46(19) . . . . ?
C10 C14 C15 C16 -0.2(3) . . . . ?
C11 C10 C14 O4 4.7(3) . . . . ?
C11 C10 C14 C15 -174.50(19) . . . . ?
C11 C12 C13 O3 -174.7(2) . . . . ?
C11 C12 C13 O4 5.3(3) . . . . ?
C11 C12 C19 C20 89.8(3) . . . . ?
C12 C19 C20 O2 -51.1(3) . . . . ?
C12 C19 C20 N1 129.8(2) . . . . ?
C13 O4 C14 C10 -4.0(3) . . . . ?
C13 O4 C14 C15 175.21(19) . . . . ?
C13 C12 C19 C20 -89.2(2) . . . . ?
C14 O4 C13 O3 179.1(2) . . . . ?
C14 O4 C13 C12 -0.9(3) . . . . ?
C14 C10 C11 C12 -0.4(3) . . . . ?
C14 C10 C11 C18 179.31(19) . . . . ?
C14 C15 C16 O5 179.3(2) . . . . ?
C14 C15 C16 C8 0.1(3) . . . . ?
C16 O5 C17 C7 -1.1(2) . . . . ?
C16 C8 C9 C10 1.5(3) . . . . ?
C17 O5 C16 C8 0.9(2) . . . . ?
C17 O5 C16 C15 -178.5(2) . . . . ?
C17 C7 C8 C9 179.3(2) . . . . ?
C17 C7 C8 C16 -0.2(2) . . . . ?
C18 C11 C12 C13 175.8(2) . . . . ?
C18 C11 C12 C19 -3.2(3) . . . . ?
C19 C12 C13 O3 4.4(3) . . . . ?
C19 C12 C13 O4 -175.62(18) . . . . ?
C20 O2 C21 S1 -177.07(15) . . . . ?
C20 O2 C21 N2 -1.1(2) . . . . ?
C20 N1 N2 C21 -0.9(2) . . . . ?
C21 S1 C22 C23 70.75(18) . . . . ?
C21 O2 C20 N1 0.5(2) . . . . ?
C21 O2 C20 C19 -178.77(19) . . . . ?
C22 S1 C21 O2 -76.09(18) . . . . ?
C22 S1 C21 N2 108.4(2) . . . . ?
C22 C23 C24 C25 -176.5(2) . . . . ?
C22 C23 C28 C27 177.7(2) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C24 C23 C28 C27 0.1(3) . . . . ?
C24 C25 C26 C27 -1.0(3) . . . . ?
C24 C25 C26 C29 178.6(2) . . . . ?
C25 C26 C27 C28 2.1(3) . . . . ?
C25 C26 C29 C30 -6.2(3) . . . . ?
C25 C26 C29 C31 -124.7(2) . . . . ?
C25 C26 C29 C32 115.4(2) . . . . ?
C26 C27 C28 C23 -1.7(3) . . . . ?
C27 C26 C29 C30 173.4(2) . . . . ?
C27 C26 C29 C31 54.9(3) . . . . ?
C27 C26 C29 C32 -65.0(3) . . . . ?
C28 C23 C24 C25 1.0(3) . . . . ?
C29 C26 C27 C28 -177.5(2) . . . . ?
