data_m23398 
 
_audit_creation_method            'SHELXL-2019/3 and CIFFIX' 
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2025). 
# CIFFIX: https://xray.uky.edu/Resources/scripts/ciffix 
_audit_update_record              ? 
 
_shelx_SHELXL_version_number      '2019/3' 
 
_publ_section_exptl_refinement 
; 
H atoms were found in difference Fourier maps, but subsequently included 
in the refinement using riding models, with constrained distances set to 
0.95 Å (Cₛₚ₂H) and 0.99 Å (R₂CH₂).  Uiso(H) values were set to 
1.2Ueq of the attached atom. 
; 
 
_publ_section_references 
; 
Bruker-AXS (2023). 
  APEX5 Bruker-AXS Inc., Madison, WI, USA. 
 
Hope, H. (1994). 
  Prog. Inorg. Chem. 41, 1--19. 
 
Krause, L., Herbst-Irmer, R., Sheldrick, G.M. & Stalke, D. (2015). 
  J. Appl. Cryst. 48, 3--10. 
 
Parkin, S. & Hope, H. (1998). 
  J. Appl. Cryst. 31, 945--953. 
 
Parkin, S. (2000). 
  Acta Cryst. A56, 157--162. 
 
Parkin, S. (2013). 
  CIFFIX, https://xray.uky.edu/Resources/scripts/ciffix 
 
Sheldrick, G.M. (2008). 
  Acta Cryst. A64, 112--122. 
 
Sheldrick, G.M. (2015a). 
  Acta Cryst. A71, 3--8. 
 
Sheldrick, G.M. (2015b). 
  Acta Cryst. C71, 3--8. 
 
Spek, A.L. (2020). 
  Acta Cryst. E76, 1--11. 
 
Westrip, S.P. (2010). 
  J. Appl. Cryst. 43, 920--925. 
; 
 
_publ_section_acknowledgements 
; 
The D8 Venture diffractometer was funded by the NSF (MRI CHE1625732), 
and by the University of Kentucky. 
; 
 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C21 H13 N5 O2 S2, C4 H8 O' 
_chemical_formula_sum             'C25 H21 N5 O3 S2' 
_chemical_formula_weight          503.59 
 
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' 
 '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' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/n' 
_space_group_name_Hall            '-P 2yn' 
 
_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+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
 
_cell_length_a                    16.4044(5) 
_cell_length_b                    7.7248(3) 
_cell_length_c                    18.3966(8) 
_cell_angle_alpha                 90 
_cell_angle_beta                  96.665(1) 
_cell_angle_gamma                 90 
_cell_volume                      2315.48(15) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100.0(2) 
_cell_measurement_reflns_used     9659 
_cell_measurement_theta_min       2.86 
_cell_measurement_theta_max       27.49 
 
_exptl_crystal_description        'cut block' 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.445 
_exptl_crystal_F_000              1048 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.140 
_exptl_crystal_size_mid           0.120 
_exptl_crystal_size_min           0.100 
_exptl_absorpt_coefficient_mu     0.270 
_shelx_estimated_absorpt_T_min    0.963 
_shelx_estimated_absorpt_T_max    0.974 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.853 
_exptl_absorpt_correction_T_max   0.928 
_exptl_absorpt_process_details    'SADABS (Krause et al., 2015)' 
_exptl_absorpt_special_details 
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by X-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the X-ray beam cross section, absorption by the crystal 
mount, scan truncation etc. These account, by and large, for the difference 
between SHELX estimates of Tmin and Tmax and the _exptl_absorpt_correction_ 
values. 
; 
 
_exptl_special_details 
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 100K. 
; 
 
_diffrn_ambient_temperature       100.0(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'microsource' 
_diffrn_measurement_device_type   'Bruker D8 Venture dual source' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  7.41 
_diffrn_reflns_number             41036 
_diffrn_reflns_av_unetI/netI      0.0337 
_diffrn_reflns_av_R_equivalents   0.0557 
_diffrn_reflns_limit_h_min        -21 
_diffrn_reflns_limit_h_max        21 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        8 
_diffrn_reflns_limit_l_min        -23 
_diffrn_reflns_limit_l_max        23 
_diffrn_reflns_theta_min          2.229 
_diffrn_reflns_theta_max          27.505 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max                0.998 
_diffrn_measured_fraction_theta_full               0.998 
_diffrn_reflns_Laue_measured_fraction_max          0.998 
_diffrn_reflns_Laue_measured_fraction_full         0.998 
_diffrn_reflns_point_group_measured_fraction_max   0.998 
_diffrn_reflns_point_group_measured_fraction_full  0.998 
 
_reflns_number_total              5306 
_reflns_number_gt                 4741 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
_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        'APEX5 (Bruker-AXS, 2023)' 
_computing_cell_refinement        'APEX5 (Bruker-AXS, 2023)' 
_computing_data_reduction         'APEX5 (Bruker-AXS, 2023)' 
_computing_structure_solution     'SHELXT (Sheldrick, 2015a)' 
_computing_structure_refinement   'SHELXL-2019/3 (Sheldrick, 2015b)' 
_computing_molecular_graphics     'XP in SHELXTL (Sheldrick, 2008)' 
_computing_publication_material 
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)' 
 
_refine_special_details 
; 
Refinement progress was checked using Platon (Spek, 2020) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
; 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0290P)²+1.3318P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    mixed 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          5306 
_refine_ls_number_parameters      322 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0362 
_refine_ls_R_factor_gt            0.0313 
_refine_ls_wR_factor_ref          0.0809 
_refine_ls_wR_factor_gt           0.0775 
_refine_ls_goodness_of_fit_ref    1.052 
_refine_ls_restrained_S_all       1.052 
_refine_ls_shift/su_max           0.001 
_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 
S1 S 0.34739(2) 0.52627(4) 0.25355(2) 0.01461(8) Uani 1 1 d . . . . . 
S2 S 0.77605(2) -0.26824(4) 0.50946(2) 0.01762(9) Uani 1 1 d . . . . . 
O1 O 0.31781(5) 0.22120(12) 0.30984(5) 0.0193(2) Uani 1 1 d . . . . . 
O2 O 0.60927(6) -0.31957(12) 0.50396(5) 0.0189(2) Uani 1 1 d . . . . . 
N1 N 0.50696(6) 0.54917(14) 0.28611(6) 0.0156(2) Uani 1 1 d . . . . . 
N2 N 0.45284(7) 0.29171(14) 0.32657(6) 0.0147(2) Uani 1 1 d . . . . . 
H2N H 0.5019(10) 0.264(2) 0.3434(8) 0.018 Uiso 1 1 d . U . . . 
N3 N 0.48610(6) -0.01341(14) 0.39868(6) 0.0141(2) Uani 1 1 d . . . . . 
N4 N 0.64563(7) -0.09703(15) 0.43352(6) 0.0163(2) Uani 1 1 d . . . . . 
H4N H 0.631(1) -0.015(2) 0.4069(9) 0.020 Uiso 1 1 d . U . . . 
N5 N 0.77684(7) -0.04752(15) 0.40193(6) 0.0177(2) Uani 1 1 d . . . . . 
C1 C 0.44390(7) 0.45018(16) 0.29157(7) 0.0141(2) Uani 1 1 d . . . . . 
C2 C 0.48100(8) 0.69983(17) 0.24906(7) 0.0148(2) Uani 1 1 d . . . . . 
C3 C 0.53262(8) 0.83478(17) 0.23254(7) 0.0170(3) Uani 1 1 d . . . . . 
H3 H 0.590116 0.828299 0.246637 0.020 Uiso 1 1 calc R U . . . 
C4 C 0.49863(8) 0.97760(18) 0.19540(7) 0.0180(3) Uani 1 1 d . . . . . 
H4A H 0.533402 1.068433 0.182772 0.022 Uiso 1 1 calc R U . . . 
C5 C 0.41372(8) 0.99076(17) 0.17604(7) 0.0175(3) Uani 1 1 d . . . . . 
H5 H 0.391600 1.091922 0.151870 0.021 Uiso 1 1 calc R U . . . 
C6 C 0.36161(8) 0.85837(17) 0.19164(7) 0.0168(3) Uani 1 1 d . . . . . 
H6 H 0.304022 0.866774 0.178405 0.020 Uiso 1 1 calc R U . . . 
C7 C 0.39632(8) 0.71238(16) 0.22737(7) 0.0142(2) Uani 1 1 d . . . . . 
C8 C 0.38810(8) 0.18555(17) 0.33419(7) 0.0151(2) Uani 1 1 d . . . . . 
C9 C 0.40767(8) 0.01922(17) 0.37428(7) 0.0148(2) Uani 1 1 d . . . . . 
C10 C 0.34333(8) -0.09347(18) 0.38367(7) 0.0176(3) Uani 1 1 d . . . . . 
H10 H 0.288471 -0.065410 0.365068 0.021 Uiso 1 1 calc R U . . . 
C11 C 0.36131(8) -0.24715(18) 0.42073(7) 0.0190(3) Uani 1 1 d . . . . . 
H11 H 0.318970 -0.327264 0.427718 0.023 Uiso 1 1 calc R U . . . 
C12 C 0.44196(8) -0.28223(17) 0.44746(7) 0.0175(3) Uani 1 1 d . . . . . 
H12 H 0.456063 -0.385925 0.473715 0.021 Uiso 1 1 calc R U . . . 
C13 C 0.50191(8) -0.16192(17) 0.43494(7) 0.0149(2) Uani 1 1 d . . . . . 
C14 C 0.58989(8) -0.20080(17) 0.46153(7) 0.0156(3) Uani 1 1 d . . . . . 
C15 C 0.72952(8) -0.12619(17) 0.44287(7) 0.0158(2) Uani 1 1 d . . . . . 
C16 C 0.85776(8) -0.09986(17) 0.42073(7) 0.0168(3) Uani 1 1 d . . . . . 
C17 C 0.92450(8) -0.04397(18) 0.38611(7) 0.0202(3) Uani 1 1 d . . . . . 
H17 H 0.917025 0.036950 0.347016 0.024 Uiso 1 1 calc R U . . . 
C18 C 1.00142(8) -0.10849(19) 0.40974(8) 0.0217(3) Uani 1 1 d . . . . . 
H18 H 1.047222 -0.071344 0.386593 0.026 Uiso 1 1 calc R U . . . 
C19 C 1.01305(8) -0.22749(19) 0.46712(8) 0.0220(3) Uani 1 1 d . . . . . 
H19 H 1.066672 -0.269728 0.482489 0.026 Uiso 1 1 calc R U . . . 
C20 C 0.94760(8) -0.28504(19) 0.50203(7) 0.0209(3) Uani 1 1 d . . . . . 
H20 H 0.955497 -0.366439 0.540925 0.025 Uiso 1 1 calc R U . . . 
C21 C 0.86983(8) -0.21963(17) 0.47825(7) 0.0171(3) Uani 1 1 d . . . . . 
 
 
_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 
S1 C7 1.7415(13) . ? 
S1 C1 1.7562(13) . ? 
S2 C21 1.7443(13) . ? 
S2 C15 1.7522(13) . ? 
O1 C8 1.2191(16) . ? 
O2 C14 1.2226(16) . ? 
N1 C1 1.2995(16) . ? 
N1 C2 1.3904(16) . ? 
N2 C8 1.3618(16) . ? 
N2 C1 1.3829(17) . ? 
N2 H2N 0.856(16) . ? 
N3 C9 1.3365(16) . ? 
N3 C13 1.3371(16) . ? 
N4 C14 1.3615(17) . ? 
N4 C15 1.3853(17) . ? 
N4 H4N 0.818(17) . ? 
N5 C15 1.2942(17) . ? 
N5 C16 1.3923(17) . ? 
C2 C3 1.3986(18) . ? 
C2 C7 1.4034(17) . ? 
C3 C4 1.3807(19) . ? 
C3 H3 0.9500 . ? 
C4 C5 1.4008(18) . ? 
C4 H4A 0.9500 . ? 
C5 C6 1.3842(18) . ? 
C5 H5 0.9500 . ? 
C6 C7 1.3933(18) . ? 
C6 H6 0.9500 . ? 
C8 C9 1.4977(18) . ? 
C9 C10 1.3942(18) . ? 
C10 C11 1.3837(19) . ? 
C10 H10 0.9500 . ? 
C11 C12 1.3837(19) . ? 
C11 H11 0.9500 . ? 
C12 C13 1.3916(18) . ? 
C12 H12 0.9500 . ? 
C13 C14 1.4995(18) . ? 
C16 C17 1.3973(18) . ? 
C16 C21 1.4022(18) . ? 
C17 C18 1.3792(19) . ? 
C17 H17 0.9500 . ? 
C18 C19 1.396(2) . ? 
C18 H18 0.9500 . ? 
C19 C20 1.3867(19) . ? 
C19 H19 0.9500 . ? 
C20 C21 1.3946(19) . ? 
C20 H20 0.9500 . ? 
O1S C4S 1.4467(15) . ? 
O1S C1S 1.4468(17) . ? 
C1S C2S 1.5188(19) . ? 
C1S H1S1 0.9900 . ? 
C1S H1S2 0.9900 . ? 
C2S C3S 1.523(2) . ? 
C2S H2SA 0.9900 . ? 
C2S H2SB 0.9900 . ? 
C3S C4S 1.5095(18) . ? 
C3S H3SA 0.9900 . ? 
C3S H3SB 0.9900 . ? 
C4S H4S1 0.9900 . ? 
C4S H4S2 0.9900 . ? 
 
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 
C7 S1 C1 87.90(6) . . ? 
C21 S2 C15 87.96(6) . . ? 
C1 N1 C2 109.22(11) . . ? 
C8 N2 C1 122.63(11) . . ? 
C8 N2 H2N 121.5(11) . . ? 
C1 N2 H2N 115.9(11) . . ? 
C9 N3 C13 116.92(11) . . ? 
C14 N4 C15 123.94(12) . . ? 
C14 N4 H4N 121.2(11) . . ? 
C15 N4 H4N 114.7(11) . . ? 
C15 N5 C16 109.76(11) . . ? 
N1 C1 N2 120.97(11) . . ? 
N1 C1 S1 117.46(10) . . ? 
N2 C1 S1 121.57(9) . . ? 
N1 C2 C3 124.87(12) . . ? 
N1 C2 C7 115.72(11) . . ? 
C3 C2 C7 119.41(12) . . ? 
C4 C3 C2 118.89(12) . . ? 
C4 C3 H3 120.6 . . ? 
C2 C3 H3 120.6 . . ? 
C3 C4 C5 121.09(12) . . ? 
C3 C4 H4A 119.5 . . ? 
C5 C4 H4A 119.5 . . ? 
C6 C5 C4 120.89(12) . . ? 
C6 C5 H5 119.6 . . ? 
C4 C5 H5 119.6 . . ? 
C5 C6 C7 117.87(12) . . ? 
C5 C6 H6 121.1 . . ? 
C7 C6 H6 121.1 . . ? 
C6 C7 C2 121.79(12) . . ? 
C6 C7 S1 128.5(1) . . ? 
C2 C7 S1 109.7(1) . . ? 
O1 C8 N2 122.81(12) . . ? 
O1 C8 C9 120.95(12) . . ? 
N2 C8 C9 116.24(11) . . ? 
N3 C9 C10 123.62(12) . . ? 
N3 C9 C8 118.04(11) . . ? 
C10 C9 C8 118.33(12) . . ? 
C11 C10 C9 118.40(12) . . ? 
C11 C10 H10 120.8 . . ? 
C9 C10 H10 120.8 . . ? 
C10 C11 C12 118.91(12) . . ? 
C10 C11 H11 120.5 . . ? 
C12 C11 H11 120.5 . . ? 
C11 C12 C13 118.38(12) . . ? 
C11 C12 H12 120.8 . . ? 
C13 C12 H12 120.8 . . ? 
N3 C13 C12 123.76(12) . . ? 
N3 C13 C14 117.27(11) . . ? 
C12 C13 C14 118.96(12) . . ? 
O2 C14 N4 123.18(12) . . ? 
O2 C14 C13 121.85(12) . . ? 
N4 C14 C13 114.95(11) . . ? 
N5 C15 N4 120.37(12) . . ? 
N5 C15 S2 117.31(10) . . ? 
N4 C15 S2 122.31(10) . . ? 
N5 C16 C17 124.88(12) . . ? 
N5 C16 C21 115.22(11) . . ? 
C17 C16 C21 119.89(12) . . ? 
C18 C17 C16 118.77(13) . . ? 
C18 C17 H17 120.6 . . ? 
C16 C17 H17 120.6 . . ? 
C17 C18 C19 121.07(13) . . ? 
C17 C18 H18 119.5 . . ? 
C19 C18 H18 119.5 . . ? 
C20 C19 C18 121.07(13) . . ? 
C20 C19 H19 119.5 . . ? 
C18 C19 H19 119.5 . . ? 
C19 C20 C21 117.89(13) . . ? 
C19 C20 H20 121.1 . . ? 
C21 C20 H20 121.1 . . ? 
C20 C21 C16 121.32(12) . . ? 
C20 C21 S2 128.93(11) . . ? 
C16 C21 S2 109.74(10) . . ? 
C4S O1S C1S 108.66(9) . . ? 
O1S C1S C2S 106.09(11) . . ? 
O1S C1S H1S1 110.5 . . ? 
C2S C1S H1S1 110.5 . . ? 
O1S C1S H1S2 110.5 . . ? 
C2S C1S H1S2 110.5 . . ? 
H1S1 C1S H1S2 108.7 . . ? 
C1S C2S C3S 101.66(11) . . ? 
C1S C2S H2SA 111.4 . . ? 
C3S C2S H2SA 111.4 . . ? 
C1S C2S H2SB 111.4 . . ? 
C3S C2S H2SB 111.4 . . ? 
H2SA C2S H2SB 109.3 . . ? 
C4S C3S C2S 101.69(11) . . ? 
C4S C3S H3SA 111.4 . . ? 
C2S C3S H3SA 111.4 . . ? 
C4S C3S H3SB 111.4 . . ? 
C2S C3S H3SB 111.4 . . ? 
H3SA C3S H3SB 109.3 . . ? 
O1S C4S C3S 106.41(10) . . ? 
O1S C4S H4S1 110.4 . . ? 
C3S C4S H4S1 110.4 . . ? 
O1S C4S H4S2 110.4 . . ? 
C3S C4S H4S2 110.4 . . ? 
H4S1 C4S H4S2 108.6 . . ? 
 
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 
C2 N1 C1 N2 -179.72(11) . . . . ? 
C2 N1 C1 S1 -0.21(14) . . . . ? 
C8 N2 C1 N1 179.12(12) . . . . ? 
C8 N2 C1 S1 -0.36(17) . . . . ? 
C7 S1 C1 N1 -0.18(10) . . . . ? 
C7 S1 C1 N2 179.33(11) . . . . ? 
C1 N1 C2 C3 -179.20(12) . . . . ? 
C1 N1 C2 C7 0.63(15) . . . . ? 
N1 C2 C3 C4 -179.95(12) . . . . ? 
C7 C2 C3 C4 0.24(18) . . . . ? 
C2 C3 C4 C5 1.72(19) . . . . ? 
C3 C4 C5 C6 -2.0(2) . . . . ? 
C4 C5 C6 C7 0.24(19) . . . . ? 
C5 C6 C7 C2 1.75(19) . . . . ? 
C5 C6 C7 S1 -179.55(10) . . . . ? 
N1 C2 C7 C6 178.16(11) . . . . ? 
C3 C2 C7 C6 -2.01(19) . . . . ? 
N1 C2 C7 S1 -0.76(14) . . . . ? 
C3 C2 C7 S1 179.08(10) . . . . ? 
C1 S1 C7 C6 -178.32(12) . . . . ? 
C1 S1 C7 C2 0.50(9) . . . . ? 
C1 N2 C8 O1 1.10(19) . . . . ? 
C1 N2 C8 C9 -179.25(11) . . . . ? 
C13 N3 C9 C10 -1.11(18) . . . . ? 
C13 N3 C9 C8 179.36(10) . . . . ? 
O1 C8 C9 N3 179.01(11) . . . . ? 
N2 C8 C9 N3 -0.65(17) . . . . ? 
O1 C8 C9 C10 -0.55(18) . . . . ? 
N2 C8 C9 C10 179.79(11) . . . . ? 
N3 C9 C10 C11 0.50(19) . . . . ? 
C8 C9 C10 C11 -179.97(11) . . . . ? 
C9 C10 C11 C12 0.54(19) . . . . ? 
C10 C11 C12 C13 -0.89(19) . . . . ? 
C9 N3 C13 C12 0.72(18) . . . . ? 
C9 N3 C13 C14 179.11(11) . . . . ? 
C11 C12 C13 N3 0.27(19) . . . . ? 
C11 C12 C13 C14 -178.10(11) . . . . ? 
C15 N4 C14 O2 7.8(2) . . . . ? 
C15 N4 C14 C13 -170.63(11) . . . . ? 
N3 C13 C14 O2 169.16(11) . . . . ? 
C12 C13 C14 O2 -12.37(18) . . . . ? 
N3 C13 C14 N4 -12.34(16) . . . . ? 
C12 C13 C14 N4 166.14(11) . . . . ? 
C16 N5 C15 N4 -178.96(11) . . . . ? 
C16 N5 C15 S2 1.15(15) . . . . ? 
C14 N4 C15 N5 164.29(12) . . . . ? 
C14 N4 C15 S2 -15.82(18) . . . . ? 
C21 S2 C15 N5 -0.92(11) . . . . ? 
C21 S2 C15 N4 179.19(11) . . . . ? 
C15 N5 C16 C17 178.15(13) . . . . ? 
C15 N5 C16 C21 -0.82(16) . . . . ? 
N5 C16 C17 C18 -179.06(13) . . . . ? 
C21 C16 C17 C18 -0.1(2) . . . . ? 
C16 C17 C18 C19 0.0(2) . . . . ? 
C17 C18 C19 C20 0.2(2) . . . . ? 
C18 C19 C20 C21 -0.3(2) . . . . ? 
C19 C20 C21 C16 0.2(2) . . . . ? 
C19 C20 C21 S2 178.85(11) . . . . ? 
N5 C16 C21 C20 179.05(12) . . . . ? 
C17 C16 C21 C20 0.0(2) . . . . ? 
N5 C16 C21 S2 0.16(15) . . . . ? 
C17 C16 C21 S2 -178.86(10) . . . . ? 
C15 S2 C21 C20 -178.41(14) . . . . ? 
C15 S2 C21 C16 0.37(10) . . . . ? 
C4S O1S C1S C2S 12.34(15) . . . . ? 
O1S C1S C2S C3S -32.06(15) . . . . ? 
C1S C2S C3S C4S 38.61(14) . . . . ? 
C1S O1S C4S C3S 12.90(14) . . . . ? 
C2S C3S C4S O1S -32.48(13) . . . . ? 
 
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 
N2 H2N O1S  0.856(16) 2.104(17) 2.9341(14) 163.1(15) . yes 
N4 H4N O1S  0.818(17) 2.128(18) 2.9106(15) 160.3(15) . yes 
C6 H6 O1  0.95 2.33 3.1253(16) 141.5 2 yes 
C10 H10 S1  0.95 3.02 3.8966(14) 154.6 2_545 yes 
C12 H12 O2  0.95 2.57 3.3378(16) 138.3 3_646 yes 
C1S H1S2 O2  0.99 2.48 3.4141(17) 157.7 1_565 yes 
C3S H3SA N5  0.99 2.67 3.6239(17) 161.5 2_655 yes 
 
_refine_diff_density_max    0.327 
_refine_diff_density_min   -0.287 
_refine_diff_density_rms    0.051 
 
 

