data_publication_text
_publ_requested_journal          'J. Am. Chem. Soc.'
_publ_contact_author_name        'Prof. Dr. Thomas M.  Klapötke'
_publ_contact_author_address     
;
Department of Chemistry
Ludwig Maximilian University
Butenandtstr. 5-13 (D)
81377 Munich
Germany
;
_publ_contact_author_email       tmk@cup.uni-muenchen.de
_publ_contact_author_phone       +49-89-2180-77491
loop_
_publ_author_name
_publ_author_address
'Dominik Dosch'
;
Department of Chemistry
Ludwig Maximilian University
Butenandtstr. 5-13 (D)
81377 Munich
Germany
;
'Marco Reichel'
;
Department of Chemistry
Ludwig Maximilian University
Butenandtstr. 5-13 (D)
81377 Munich
Germany
;
'Konstantin Karaghiosoff'
;
Department of Chemistry
Ludwig Maximilian University
Butenandtstr. 5-13 (D)
81377 Munich
Germany
;
'Thomas M. Klapötke'
;
Department of Chemistry
Ludwig Maximilian University
Butenandtstr. 5-13 (D)
81377 Munich
Germany
;
 
data_test1 
  
_audit_creation_method            'SHELXL-2018/1' 
_shelx_SHELXL_version_number      '2018/1' 
_chemical_name_systematic         
;
bis(2,4,6-trinitrophenyl)sulfane
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          
'C12 H4 N6 O12 S' 
_chemical_formula_sum 
'C12 H4 N6 O12 S' 
_chemical_formula_weight          456.27 
  
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' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            4 
_space_group_name_H-M_alt         'P 21' 
_space_group_name_Hall            'P 2yb' 
  
_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. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
  
_cell_length_a                    10.9756(5) 
_cell_length_b                    11.0066(4) 
_cell_length_c                    14.0260(5) 
_cell_angle_alpha                 90 
_cell_angle_beta                  104.829(4) 
_cell_angle_gamma                 90 
_cell_volume                      1637.96(12) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     298(2) 
_cell_measurement_reflns_used     3876 
_cell_measurement_theta_min       4.2540 
_cell_measurement_theta_max       31.5220 
  
_exptl_crystal_description        'neadle' 
_exptl_crystal_colour             'yellow' 
_exptl_crystal_density_meas       . 
_exptl_crystal_density_method     . 
_exptl_crystal_density_diffrn     1.850 
_exptl_crystal_F_000              920  
_exptl_crystal_size_max           0.200 
_exptl_crystal_size_mid           0.050 
_exptl_crystal_size_min           0.050 
_exptl_absorpt_coefficient_mu     0.288 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.91575 
_exptl_absorpt_correction_T_max   1.00000 
_exptl_absorpt_process_details     
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
; 
_diffrn_ambient_temperature       298(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'fine-focus sealed X-ray tube' 
_diffrn_measurement_device_type   'Xcalibur, Sapphire3' 
_diffrn_measurement_method        'ω scans' 
_diffrn_detector_area_resol_mean  15.9809 
_diffrn_reflns_number             15113 
_diffrn_reflns_av_unetI/netI      0.0643 
_diffrn_reflns_av_R_equivalents   0.0404 
_diffrn_reflns_limit_h_min        -14 
_diffrn_reflns_limit_h_max        14 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        10 
_diffrn_reflns_theta_min          4.172 
_diffrn_reflns_theta_max          28.278 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.996 
_diffrn_measured_fraction_theta_full  0.994 
_diffrn_reflns_Laue_measured_fraction_max    0.996 
_diffrn_reflns_Laue_measured_fraction_full   0.994 
_diffrn_reflns_point_group_measured_fraction_max   0.966 
_diffrn_reflns_point_group_measured_fraction_full  0.975 
_reflns_number_total              7871 
_reflns_number_gt                 6705 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.845 
_reflns_Friedel_fraction_max      0.933 
_reflns_Friedel_fraction_full     0.954 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' 
_computing_cell_refinement        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' 
_computing_data_reduction         'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-2018/1 (Sheldrick, 2018)' 
_computing_molecular_graphics     
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
; 
_computing_publication_material   
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
; 
_refine_special_details           
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0275P)²] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      'direct' 
_atom_sites_solution_secondary    'difmap' 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2553 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    0.08(5) 
_chemical_absolute_configuration  unk 
_refine_ls_number_reflns          7871 
_refine_ls_number_parameters      559 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0556 
_refine_ls_R_factor_gt            0.0424 
_refine_ls_wR_factor_ref          0.0817 
_refine_ls_wR_factor_gt           0.0755 
_refine_ls_goodness_of_fit_ref    1.032 
_refine_ls_restrained_S_all       1.032 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
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 
N1 N 0.1076(3) 0.1126(3) 0.6670(2) 0.0228(7) Uani 1 1 d . . . . . 
S1 S 0.33927(9) 0.46940(8) 0.21204(6) 0.01803(19) Uani 1 1 d . . . . . 
O1 O 0.0901(3) 0.0033(3) 0.6555(2) 0.0331(7) Uani 1 1 d . . . . . 
C1 C 0.1965(3) 0.2806(3) 0.5874(2) 0.0152(7) Uani 1 1 d . . . . . 
O2 O 0.1199(3) 0.1666(3) 0.74494(19) 0.0291(7) Uani 1 1 d . . . . . 
S2 S 0.30336(9) 0.31610(8) 0.70207(6) 0.0191(2) Uani 1 1 d . . . . . 
N2 N -0.0583(3) 0.1783(3) 0.3145(2) 0.0204(7) Uani 1 1 d . . . . . 
C2 C 0.1103(4) 0.1846(3) 0.5797(3) 0.0175(8) Uani 1 1 d . . . . . 
C18 C 0.1927(3) 0.4665(3) 0.0110(3) 0.0163(7) Uani 1 1 d . . . . . 
O18 O 0.3648(3) 0.3356(2) 0.0355(2) 0.0312(7) Uani 1 1 d . . . . . 
C4 C 0.0299(3) 0.2144(3) 0.4085(3) 0.0169(8) Uani 1 1 d . . . . . 
O4 O -0.0716(3) 0.2498(2) 0.24541(18) 0.0251(6) Uani 1 1 d . . . . . 
N4 N 0.4076(3) 0.1404(3) 0.5589(2) 0.0197(7) Uani 1 1 d . . . . . 
C3 C 0.0293(4) 0.1496(3) 0.4920(3) 0.0188(8) Uani 1 1 d . . . . . 
H3 H -0.024510 0.083735 0.489390 0.023 Uiso 1 1 calc R U . . . 
O3 O -0.1104(3) 0.0803(3) 0.31125(19) 0.0265(6) Uani 1 1 d . . . . . 
N3 N 0.2760(3) 0.4462(3) 0.4959(2) 0.0191(7) Uani 1 1 d . . . . . 
C5 C 0.1109(3) 0.3099(3) 0.4097(3) 0.0178(7) Uani 1 1 d . . . . . 
H5 H 0.111332 0.351955 0.352271 0.021 Uiso 1 1 calc R U . . . 
O5 O 0.3412(3) 0.4399(3) 0.4375(2) 0.0286(7) Uani 1 1 d . . . . . 
N5 N 0.5127(3) 0.4995(3) 0.7822(2) 0.0213(7) Uani 1 1 d . . . . . 
C6 C 0.1914(3) 0.3411(3) 0.4989(3) 0.0160(7) Uani 1 1 d . . . . . 
O6 O 0.2736(3) 0.5308(3) 0.5508(2) 0.0339(7) Uani 1 1 d . . . . . 
N6 N 0.7864(3) 0.3751(3) 0.5749(2) 0.0221(7) Uani 1 1 d . . . . . 
C15 C 0.0424(4) 0.6559(3) 0.0424(3) 0.0182(8) Uani 1 1 d . . . . . 
H15 H -0.007283 0.720395 0.053114 0.022 Uiso 1 1 calc R U . . . 
O15 O -0.1232(3) 0.7497(2) -0.11852(19) 0.0255(6) Uani 1 1 d . . . . . 
C7 C 0.4472(3) 0.3260(3) 0.6667(2) 0.0153(7) Uani 1 1 d . . . . . 
C16 C 0.0254(3) 0.6046(3) -0.0497(3) 0.0162(7) Uani 1 1 d . . . . . 
O16 O -0.1081(3) 0.5897(2) -0.20523(18) 0.0218(6) Uani 1 1 d . . . . . 
C8 C 0.4832(3) 0.2474(3) 0.6000(3) 0.0158(7) Uani 1 1 d . . . . . 
O8 O 0.3663(3) 0.0764(2) 0.6149(2) 0.0277(7) Uani 1 1 d . . . . . 
N8 N -0.0764(3) 0.6517(3) -0.1308(2) 0.0188(7) Uani 1 1 d . . . . . 
C19 C 0.4778(3) 0.4895(3) 0.1712(2) 0.0150(7) Uani 1 1 d . . . . . 
O19 O 0.3733(3) 0.7332(2) 0.1374(2) 0.0290(7) Uani 1 1 d . . . . . 
C9 C 0.5914(3) 0.2625(3) 0.5680(3) 0.0171(8) Uani 1 1 d . . . . . 
H9 H 0.610258 0.210589 0.521478 0.021 Uiso 1 1 calc R U . . . 
O9 O 0.8075(3) 0.3016(3) 0.5159(2) 0.0372(8) Uani 1 1 d . . . . . 
N9 N 0.2590(3) 0.3587(3) -0.0137(2) 0.0183(7) Uani 1 1 d . . . . . 
C20 C 0.4911(3) 0.5741(3) 0.1001(2) 0.0140(7) Uani 1 1 d . . . . . 
O20 O 0.3678(3) 0.7023(3) -0.0166(2) 0.0327(7) Uani 1 1 d . . . . . 
C22 C 0.6799(3) 0.4851(3) 0.0849(3) 0.0166(7) Uani 1 1 d . . . . . 
O22 O 0.8739(3) 0.4157(3) 0.0723(2) 0.0356(8) Uani 1 1 d . . . . . 
C12 C 0.5342(3) 0.4179(3) 0.7049(3) 0.0157(7) Uani 1 1 d . . . . . 
O12 O 0.4542(3) 0.4577(3) 0.83849(18) 0.0291(7) Uani 1 1 d . . . . . 
N12 N 0.5858(3) 0.3266(3) 0.2862(2) 0.0194(7) Uani 1 1 d . . . . . 
C21 C 0.5870(4) 0.5702(3) 0.0532(3) 0.0175(8) Uani 1 1 d . . . . . 
H21 H 0.588650 0.623313 0.001996 0.021 Uiso 1 1 calc R U . . . 
O21 O 0.7647(3) 0.5285(3) -0.0448(2) 0.0382(8) Uani 1 1 d . . . . . 
C11 C 0.6445(3) 0.4352(3) 0.6773(2) 0.0169(8) Uani 1 1 d . . . . . 
H11 H 0.700049 0.497292 0.704552 0.020 Uiso 1 1 calc R U . . . 
C10 C 0.6700(4) 0.3570(3) 0.6076(3) 0.0175(8) Uani 1 1 d . . . . . 
O10 O 0.8529(3) 0.4611(3) 0.6084(2) 0.0297(7) Uani 1 1 d . . . . . 
N10 N 0.4030(3) 0.6773(3) 0.0714(2) 0.0202(7) Uani 1 1 d . . . . . 
C23 C 0.6815(3) 0.4082(3) 0.1626(2) 0.0157(7) Uani 1 1 d . . . . . 
H23 H 0.748541 0.355367 0.186174 0.019 Uiso 1 1 calc R U . . . 
O23 O 0.6659(3) 0.2468(3) 0.3008(2) 0.0327(7) Uani 1 1 d . . . . . 
C13 C 0.2197(3) 0.5161(3) 0.1072(3) 0.0160(7) Uani 1 1 d . . . . . 
O13 O 0.1274(3) 0.7700(3) 0.2203(2) 0.0316(7) Uani 1 1 d . . . . . 
C24 C 0.5811(4) 0.4118(3) 0.2044(2) 0.0152(7) Uani 1 1 d . . . . . 
O24 O 0.5102(3) 0.3424(2) 0.33604(18) 0.0232(6) Uani 1 1 d . . . . . 
C14 C 0.1357(4) 0.6080(3) 0.1180(3) 0.0163(7) Uani 1 1 d . . . . . 
O14 O 0.1571(3) 0.5891(3) 0.28597(19) 0.0327(7) Uani 1 1 d . . . . . 
N7 N 0.1423(3) 0.6597(3) 0.2164(2) 0.0234(7) Uani 1 1 d . . . . . 
N11 N 0.7811(3) 0.4753(3) 0.0343(2) 0.0229(7) Uani 1 1 d . . . . . 
O7 O 0.3921(3) 0.1216(3) 0.4711(2) 0.0366(8) Uani 1 1 d . . . . . 
O11 O 0.5571(3) 0.6017(2) 0.7873(2) 0.0306(7) Uani 1 1 d . . . . . 
O17 O 0.2023(3) 0.2967(2) -0.08316(18) 0.0260(6) Uani 1 1 d . . . . . 
C17 C 0.0964(4) 0.5091(3) -0.0663(3) 0.0168(8) Uani 1 1 d . . . . . 
H17 H 0.080563 0.473174 -0.128288 0.020 Uiso 1 1 calc R U . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
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 
N1 O2 1.221(4) . ? 
N1 O1 1.223(4) . ? 
N1 C2 1.465(5) . ? 
S1 C19 1.770(4) . ? 
S1 C13 1.778(4) . ? 
C1 C6 1.397(5) . ? 
C1 C2 1.404(5) . ? 
C1 S2 1.775(4) . ? 
S2 C7 1.775(4) . ? 
N2 O3 1.216(4) . ? 
N2 O4 1.228(4) . ? 
N2 C4 1.477(5) . ? 
C2 C3 1.375(5) . ? 
C18 C17 1.388(5) . ? 
C18 C13 1.415(5) . ? 
C18 N9 1.478(5) . ? 
O18 N9 1.215(4) . ? 
C4 C3 1.373(5) . ? 
C4 C5 1.374(5) . ? 
N4 O7 1.218(4) . ? 
N4 O8 1.225(4) . ? 
N4 C8 1.471(5) . ? 
C3 H3 0.9300 . ? 
N3 O6 1.213(4) . ? 
N3 O5 1.219(4) . ? 
N3 C6 1.491(5) . ? 
C5 C6 1.378(5) . ? 
C5 H5 0.9300 . ? 
N5 O11 1.220(4) . ? 
N5 O12 1.228(4) . ? 
N5 C12 1.473(4) . ? 
N6 O10 1.213(4) . ? 
N6 O9 1.222(4) . ? 
N6 C10 1.477(5) . ? 
C15 C14 1.377(5) . ? 
C15 C16 1.379(5) . ? 
C15 H15 0.9300 . ? 
O15 N8 1.226(4) . ? 
C7 C12 1.400(5) . ? 
C7 C8 1.403(5) . ? 
C16 C17 1.363(5) . ? 
C16 N8 1.470(5) . ? 
O16 N8 1.220(4) . ? 
C8 C9 1.383(5) . ? 
C19 C20 1.399(5) . ? 
C19 C24 1.401(5) . ? 
O19 N10 1.224(4) . ? 
C9 C10 1.375(5) . ? 
C9 H9 0.9300 . ? 
N9 O17 1.222(4) . ? 
C20 C21 1.376(5) . ? 
C20 N10 1.479(4) . ? 
O20 N10 1.227(4) . ? 
C22 C21 1.372(5) . ? 
C22 C23 1.377(5) . ? 
C22 N11 1.466(5) . ? 
O22 N11 1.215(4) . ? 
C12 C11 1.375(5) . ? 
N12 O23 1.222(4) . ? 
N12 O24 1.227(4) . ? 
N12 C24 1.472(4) . ? 
C21 H21 0.9300 . ? 
O21 N11 1.226(4) . ? 
C11 C10 1.384(5) . ? 
C11 H11 0.9300 . ? 
C23 C24 1.375(5) . ? 
C23 H23 0.9300 . ? 
C13 C14 1.402(5) . ? 
O13 N7 1.227(4) . ? 
C14 N7 1.477(4) . ? 
O14 N7 1.226(4) . ? 
C17 H17 0.9300 . ? 
  
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 
O2 N1 O1 125.1(3) . . ? 
O2 N1 C2 117.6(3) . . ? 
O1 N1 C2 117.2(3) . . ? 
C19 S1 C13 102.11(17) . . ? 
C6 C1 C2 114.7(3) . . ? 
C6 C1 S2 124.6(3) . . ? 
C2 C1 S2 120.7(3) . . ? 
C1 S2 C7 100.90(16) . . ? 
O3 N2 O4 125.4(3) . . ? 
O3 N2 C4 117.8(3) . . ? 
O4 N2 C4 116.8(3) . . ? 
C3 C2 C1 123.2(3) . . ? 
C3 C2 N1 116.7(3) . . ? 
C1 C2 N1 120.0(3) . . ? 
C17 C18 C13 123.1(3) . . ? 
C17 C18 N9 114.2(3) . . ? 
C13 C18 N9 122.5(3) . . ? 
C3 C4 C5 122.1(3) . . ? 
C3 C4 N2 118.5(3) . . ? 
C5 C4 N2 119.4(3) . . ? 
O7 N4 O8 124.9(3) . . ? 
O7 N4 C8 116.8(3) . . ? 
O8 N4 C8 118.3(3) . . ? 
C4 C3 C2 118.4(3) . . ? 
C4 C3 H3 120.8 . . ? 
C2 C3 H3 120.8 . . ? 
O6 N3 O5 125.6(3) . . ? 
O6 N3 C6 117.6(3) . . ? 
O5 N3 C6 116.9(3) . . ? 
C4 C5 C6 117.7(3) . . ? 
C4 C5 H5 121.2 . . ? 
C6 C5 H5 121.2 . . ? 
O11 N5 O12 125.1(3) . . ? 
O11 N5 C12 117.9(3) . . ? 
O12 N5 C12 117.0(3) . . ? 
C5 C6 C1 123.9(3) . . ? 
C5 C6 N3 115.3(3) . . ? 
C1 C6 N3 120.8(3) . . ? 
O10 N6 O9 125.4(3) . . ? 
O10 N6 C10 117.9(3) . . ? 
O9 N6 C10 116.7(3) . . ? 
C14 C15 C16 117.4(3) . . ? 
C14 C15 H15 121.3 . . ? 
C16 C15 H15 121.3 . . ? 
C12 C7 C8 114.9(3) . . ? 
C12 C7 S2 120.4(3) . . ? 
C8 C7 S2 124.8(3) . . ? 
C17 C16 C15 122.0(3) . . ? 
C17 C16 N8 119.6(3) . . ? 
C15 C16 N8 118.3(3) . . ? 
C9 C8 C7 123.6(3) . . ? 
C9 C8 N4 114.5(3) . . ? 
C7 C8 N4 121.9(3) . . ? 
O16 N8 O15 125.0(3) . . ? 
O16 N8 C16 117.3(3) . . ? 
O15 N8 C16 117.7(3) . . ? 
C20 C19 C24 114.8(3) . . ? 
C20 C19 S1 124.7(3) . . ? 
C24 C19 S1 120.3(3) . . ? 
C10 C9 C8 117.5(3) . . ? 
C10 C9 H9 121.2 . . ? 
C8 C9 H9 121.2 . . ? 
O18 N9 O17 123.6(3) . . ? 
O18 N9 C18 119.4(3) . . ? 
O17 N9 C18 117.0(3) . . ? 
C21 C20 C19 123.5(3) . . ? 
C21 C20 N10 114.8(3) . . ? 
C19 C20 N10 121.6(3) . . ? 
C21 C22 C23 122.2(3) . . ? 
C21 C22 N11 119.1(3) . . ? 
C23 C22 N11 118.7(3) . . ? 
C11 C12 C7 123.7(3) . . ? 
C11 C12 N5 116.2(3) . . ? 
C7 C12 N5 120.0(3) . . ? 
O23 N12 O24 124.7(3) . . ? 
O23 N12 C24 118.0(3) . . ? 
O24 N12 C24 117.4(3) . . ? 
C22 C21 C20 117.5(3) . . ? 
C22 C21 H21 121.2 . . ? 
C20 C21 H21 121.2 . . ? 
C12 C11 C10 117.7(3) . . ? 
C12 C11 H11 121.2 . . ? 
C10 C11 H11 121.2 . . ? 
C9 C10 C11 122.4(3) . . ? 
C9 C10 N6 118.7(3) . . ? 
C11 C10 N6 118.9(3) . . ? 
O19 N10 O20 125.0(3) . . ? 
O19 N10 C20 117.5(3) . . ? 
O20 N10 C20 117.5(3) . . ? 
C24 C23 C22 118.1(3) . . ? 
C24 C23 H23 121.0 . . ? 
C22 C23 H23 121.0 . . ? 
C14 C13 C18 113.5(3) . . ? 
C14 C13 S1 119.1(3) . . ? 
C18 C13 S1 127.3(3) . . ? 
C23 C24 C19 123.0(3) . . ? 
C23 C24 N12 116.2(3) . . ? 
C19 C24 N12 120.8(3) . . ? 
C15 C14 C13 125.0(3) . . ? 
C15 C14 N7 114.8(3) . . ? 
C13 C14 N7 120.2(3) . . ? 
O14 N7 O13 125.7(3) . . ? 
O14 N7 C14 117.7(3) . . ? 
O13 N7 C14 116.6(3) . . ? 
O22 N11 O21 124.5(3) . . ? 
O22 N11 C22 118.8(3) . . ? 
O21 N11 C22 116.7(3) . . ? 
C16 C17 C18 118.8(3) . . ? 
C16 C17 H17 120.6 . . ? 
C18 C17 H17 120.6 . . ? 
  
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 
C6 C1 S2 C7 -47.3(3) . . . . ? 
C2 C1 S2 C7 131.4(3) . . . . ? 
C6 C1 C2 C3 1.8(5) . . . . ? 
S2 C1 C2 C3 -177.0(3) . . . . ? 
C6 C1 C2 N1 179.1(3) . . . . ? 
S2 C1 C2 N1 0.2(5) . . . . ? 
O2 N1 C2 C3 -142.4(4) . . . . ? 
O1 N1 C2 C3 36.0(5) . . . . ? 
O2 N1 C2 C1 40.2(5) . . . . ? 
O1 N1 C2 C1 -141.4(4) . . . . ? 
O3 N2 C4 C3 -13.4(5) . . . . ? 
O4 N2 C4 C3 167.5(3) . . . . ? 
O3 N2 C4 C5 165.6(3) . . . . ? 
O4 N2 C4 C5 -13.5(5) . . . . ? 
C5 C4 C3 C2 1.9(5) . . . . ? 
N2 C4 C3 C2 -179.1(3) . . . . ? 
C1 C2 C3 C4 -2.2(5) . . . . ? 
N1 C2 C3 C4 -179.5(3) . . . . ? 
C3 C4 C5 C6 -1.3(5) . . . . ? 
N2 C4 C5 C6 179.8(3) . . . . ? 
C4 C5 C6 C1 0.9(5) . . . . ? 
C4 C5 C6 N3 -179.4(3) . . . . ? 
C2 C1 C6 C5 -1.2(5) . . . . ? 
S2 C1 C6 C5 177.6(3) . . . . ? 
C2 C1 C6 N3 179.1(3) . . . . ? 
S2 C1 C6 N3 -2.1(5) . . . . ? 
O6 N3 C6 C5 124.8(4) . . . . ? 
O5 N3 C6 C5 -54.6(4) . . . . ? 
O6 N3 C6 C1 -55.5(5) . . . . ? 
O5 N3 C6 C1 125.1(4) . . . . ? 
C1 S2 C7 C12 138.9(3) . . . . ? 
C1 S2 C7 C8 -40.3(3) . . . . ? 
C14 C15 C16 C17 0.8(5) . . . . ? 
C14 C15 C16 N8 178.1(3) . . . . ? 
C12 C7 C8 C9 -4.3(5) . . . . ? 
S2 C7 C8 C9 175.0(3) . . . . ? 
C12 C7 C8 N4 175.2(3) . . . . ? 
S2 C7 C8 N4 -5.6(5) . . . . ? 
O7 N4 C8 C9 -43.8(5) . . . . ? 
O8 N4 C8 C9 135.3(3) . . . . ? 
O7 N4 C8 C7 136.7(4) . . . . ? 
O8 N4 C8 C7 -44.2(5) . . . . ? 
C17 C16 N8 O16 12.9(5) . . . . ? 
C15 C16 N8 O16 -164.4(3) . . . . ? 
C17 C16 N8 O15 -167.4(3) . . . . ? 
C15 C16 N8 O15 15.3(5) . . . . ? 
C13 S1 C19 C20 27.8(3) . . . . ? 
C13 S1 C19 C24 -147.1(3) . . . . ? 
C7 C8 C9 C10 2.9(5) . . . . ? 
N4 C8 C9 C10 -176.6(3) . . . . ? 
C17 C18 N9 O18 158.3(3) . . . . ? 
C13 C18 N9 O18 -26.0(5) . . . . ? 
C17 C18 N9 O17 -22.3(4) . . . . ? 
C13 C18 N9 O17 153.4(3) . . . . ? 
C24 C19 C20 C21 10.5(5) . . . . ? 
S1 C19 C20 C21 -164.6(3) . . . . ? 
C24 C19 C20 N10 -168.1(3) . . . . ? 
S1 C19 C20 N10 16.8(5) . . . . ? 
C8 C7 C12 C11 2.7(5) . . . . ? 
S2 C7 C12 C11 -176.6(3) . . . . ? 
C8 C7 C12 N5 -174.6(3) . . . . ? 
S2 C7 C12 N5 6.1(4) . . . . ? 
O11 N5 C12 C11 30.3(5) . . . . ? 
O12 N5 C12 C11 -147.7(3) . . . . ? 
O11 N5 C12 C7 -152.2(3) . . . . ? 
O12 N5 C12 C7 29.8(5) . . . . ? 
C23 C22 C21 C20 -2.1(5) . . . . ? 
N11 C22 C21 C20 177.8(3) . . . . ? 
C19 C20 C21 C22 -6.1(5) . . . . ? 
N10 C20 C21 C22 172.6(3) . . . . ? 
C7 C12 C11 C10 0.2(5) . . . . ? 
N5 C12 C11 C10 177.5(3) . . . . ? 
C8 C9 C10 C11 0.3(5) . . . . ? 
C8 C9 C10 N6 179.9(3) . . . . ? 
C12 C11 C10 C9 -1.8(5) . . . . ? 
C12 C11 C10 N6 178.7(3) . . . . ? 
O10 N6 C10 C9 177.9(3) . . . . ? 
O9 N6 C10 C9 -2.0(5) . . . . ? 
O10 N6 C10 C11 -2.6(5) . . . . ? 
O9 N6 C10 C11 177.5(3) . . . . ? 
C21 C20 N10 O19 -134.9(3) . . . . ? 
C19 C20 N10 O19 43.8(5) . . . . ? 
C21 C20 N10 O20 43.4(5) . . . . ? 
C19 C20 N10 O20 -137.9(4) . . . . ? 
C21 C22 C23 C24 4.9(5) . . . . ? 
N11 C22 C23 C24 -175.0(3) . . . . ? 
C17 C18 C13 C14 3.1(5) . . . . ? 
N9 C18 C13 C14 -172.2(3) . . . . ? 
C17 C18 C13 S1 179.7(3) . . . . ? 
N9 C18 C13 S1 4.4(5) . . . . ? 
C19 S1 C13 C14 -124.6(3) . . . . ? 
C19 S1 C13 C18 59.0(3) . . . . ? 
C22 C23 C24 C19 0.2(5) . . . . ? 
C22 C23 C24 N12 179.0(3) . . . . ? 
C20 C19 C24 C23 -7.5(5) . . . . ? 
S1 C19 C24 C23 167.9(3) . . . . ? 
C20 C19 C24 N12 173.8(3) . . . . ? 
S1 C19 C24 N12 -10.9(5) . . . . ? 
O23 N12 C24 C23 -11.5(5) . . . . ? 
O24 N12 C24 C23 167.2(3) . . . . ? 
O23 N12 C24 C19 167.3(3) . . . . ? 
O24 N12 C24 C19 -13.9(5) . . . . ? 
C16 C15 C14 C13 4.1(5) . . . . ? 
C16 C15 C14 N7 -175.1(3) . . . . ? 
C18 C13 C14 C15 -5.9(5) . . . . ? 
S1 C13 C14 C15 177.2(3) . . . . ? 
C18 C13 C14 N7 173.3(3) . . . . ? 
S1 C13 C14 N7 -3.5(5) . . . . ? 
C15 C14 N7 O14 136.4(4) . . . . ? 
C13 C14 N7 O14 -42.9(5) . . . . ? 
C15 C14 N7 O13 -40.8(5) . . . . ? 
C13 C14 N7 O13 139.9(4) . . . . ? 
C21 C22 N11 O22 167.4(4) . . . . ? 
C23 C22 N11 O22 -12.7(5) . . . . ? 
C21 C22 N11 O21 -13.0(5) . . . . ? 
C23 C22 N11 O21 166.9(3) . . . . ? 
C15 C16 C17 C18 -3.3(5) . . . . ? 
N8 C16 C17 C18 179.5(3) . . . . ? 
C13 C18 C17 C16 1.2(5) . . . . ? 
N9 C18 C17 C16 176.8(3) . . . . ? 
  
_refine_diff_density_max    0.388 
_refine_diff_density_min   -0.264 
_refine_diff_density_rms    0.059 
  
  
  
