# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

##Title:Folding interactions in orthanilic acid (2-amino benzene sulfonic acid) 
##containing peptides: some observations  
##Communicated Chem.Commun.
##By Gowri Priya, Debamitra Chakravarti, Vedavati G. Puranik, 
##Amol S. Kotmale, Pattuparambil R. Rajamohanan, and Gangadhar J. Sanjayan
##Division of Organic Chemistry,Central NMR Facility
##and Centre For Materials Characterisation
##National Chemical Laboratory Pune 411 008, India.
 
data_C18H27N3O7SCompound1
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             foldamers 
_chemical_melting_point           '110-113 degree centigrade'
_chemical_formula_moiety          'C18 H27 N3 O7 S' 
_chemical_formula_sum 
 'C18 H27 N3 O7 S' 
_chemical_formula_weight          429.49 
 
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' 
 
_symmetry_cell_setting            Triclinic
_symmetry_space_group_name_H-M    P-1 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    10.0269(3) 
_cell_length_b                    11.0127(3) 
_cell_length_c                    19.1212(5) 
_cell_angle_alpha                 100.996(2) 
_cell_angle_beta                  90.025(2) 
_cell_angle_gamma                 90.667(1) 
_cell_volume                      2072.5(1) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     9904
_cell_measurement_theta_min        2.30
_cell_measurement_theta_max       28.12
 
_exptl_crystal_description        needle 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.31 
_exptl_crystal_size_mid           0.12 
_exptl_crystal_size_min           0.07 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.376 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              912 
_exptl_absorpt_coefficient_mu     0.201 
_exptl_absorpt_correction_type    'multi-scan'  
_exptl_absorpt_correction_T_min   0.9403 
_exptl_absorpt_correction_T_max   0.9861 
_exptl_absorpt_process_details    'Bruker SADABS'  
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       296(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             30705 
_diffrn_reflns_av_R_equivalents   0.0366 
_diffrn_reflns_av_sigmaI/netI     0.0340 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -22 
_diffrn_reflns_limit_l_max        22 
_diffrn_reflns_theta_min          1.99 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              7277 
_reflns_number_gt                 5958 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection      'Bruker APEX2'
_computing_cell_refinement      'Bruker SAINT'
_computing_data_reduction       'Bruker SAINT'  
_computing_structure_solution   'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics   'Bruker SHELXTL PyMOL and PLATON'
_computing_publication_material 'Bruker SHELXTL'
 
_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 
 'calc w=1/[σ²(Fo²)+(0.0381P)²+1.3160P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     riding 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          7277 
_refine_ls_number_parameters      535 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0487 
_refine_ls_R_factor_gt            0.0360 
_refine_ls_wR_factor_ref          0.0893 
_refine_ls_wR_factor_gt           0.0829 
_refine_ls_goodness_of_fit_ref    1.015 
_refine_ls_restrained_S_all       1.015 
_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_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
S S 0.05860(5) 0.24554(4) 0.34801(2) 0.01646(12) Uani 1 1 d . . . 
O1 O 0.17917(12) 0.20077(12) 0.10301(7) 0.0184(3) Uani 1 1 d . . . 
O2 O 0.21108(13) 0.05189(12) 0.16997(7) 0.0206(3) Uani 1 1 d . . . 
O3 O -0.05592(13) -0.17801(12) 0.20765(7) 0.0200(3) Uani 1 1 d . . . 
O4 O 0.00391(13) 0.27996(12) 0.28532(7) 0.0197(3) Uani 1 1 d . . . 
O5 O 0.08069(13) 0.33854(12) 0.41046(7) 0.0230(3) Uani 1 1 d . . . 
O6 O 0.23440(15) -0.06148(13) 0.34213(8) 0.0294(3) Uani 1 1 d . . . 
O7 O 0.40665(14) -0.00176(13) 0.41697(8) 0.0265(3) Uani 1 1 d . . . 
N1 N 0.01037(15) 0.07854(14) 0.11995(8) 0.0168(3) Uani 1 1 d . . . 
H1 H -0.0400 0.1351 0.1094 0.020 Uiso 1 1 calc R . . 
N2 N -0.07220(15) 0.02954(14) 0.24939(8) 0.0168(3) Uani 1 1 d . . . 
H2 H -0.0695 0.1003 0.2367 0.020 Uiso 1 1 calc R . . 
N3 N 0.20051(15) 0.18413(15) 0.32427(9) 0.0202(4) Uani 1 1 d . . . 
H3 H 0.2219 0.1687 0.2799 0.024 Uiso 1 1 calc R . . 
C1 C 0.14101(19) 0.10619(17) 0.13428(10) 0.0164(4) Uani 1 1 d . . . 
C2 C -0.04922(18) -0.04360(17) 0.12159(10) 0.0168(4) Uani 1 1 d . . . 
C3 C -0.05631(18) -0.07127(17) 0.19734(10) 0.0161(4) Uani 1 1 d . . . 
C4 C -0.09277(18) 0.03011(17) 0.32237(10) 0.0164(4) Uani 1 1 d . . . 
C5 C -0.16544(19) -0.06289(17) 0.34556(10) 0.0195(4) Uani 1 1 d . . . 
H5 H -0.1989 -0.1297 0.3128 0.023 Uiso 1 1 calc R . . 
C6 C -0.18782(19) -0.05572(18) 0.41770(11) 0.0214(4) Uani 1 1 d . . . 
H6 H -0.2359 -0.1185 0.4329 0.026 Uiso 1 1 calc R . . 
C7 C -0.1401(2) 0.04281(18) 0.46741(11) 0.0219(4) Uani 1 1 d . . . 
H7 H -0.1567 0.0465 0.5156 0.026 Uiso 1 1 calc R . . 
C8 C -0.06763(19) 0.13607(18) 0.44513(10) 0.0191(4) Uani 1 1 d . . . 
H8 H -0.0354 0.2030 0.4783 0.023 Uiso 1 1 calc R . . 
C9 C -0.04329(18) 0.12915(17) 0.37316(10) 0.0161(4) Uani 1 1 d . . . 
C10 C 0.2924(2) 0.15471(19) 0.37693(12) 0.0249(5) Uani 1 1 d . . . 
H10C H 0.2629 0.1948 0.4239 0.030 Uiso 1 1 calc R . . 
H10D H 0.3798 0.1883 0.3690 0.030 Uiso 1 1 calc R . . 
C11 C 0.30454(19) 0.01812(19) 0.37541(10) 0.0208(4) Uani 1 1 d . . . 
C12 C 0.4334(2) -0.1299(2) 0.41946(12) 0.0320(5) Uani 1 1 d . . . 
H12D H 0.3526 -0.1699 0.4304 0.048 Uiso 1 1 calc R . . 
H12E H 0.4990 -0.1335 0.4556 0.048 Uiso 1 1 calc R . . 
H12F H 0.4663 -0.1710 0.3741 0.048 Uiso 1 1 calc R . . 
C13 C 0.31862(18) 0.25041(18) 0.10884(10) 0.0190(4) Uani 1 1 d . . . 
C14 C 0.3151(2) 0.34356(18) 0.05942(11) 0.0219(4) Uani 1 1 d . . . 
H14D H 0.2899 0.3021 0.0124 0.033 Uiso 1 1 calc R . . 
H14E H 0.4019 0.3808 0.0579 0.033 Uiso 1 1 calc R . . 
H14F H 0.2514 0.4065 0.0768 0.033 Uiso 1 1 calc R . . 
C15 C 0.4174(2) 0.14862(19) 0.08200(12) 0.0258(5) Uani 1 1 d . . . 
H15D H 0.4164 0.0895 0.1129 0.039 Uiso 1 1 calc R . . 
H15E H 0.5053 0.1839 0.0814 0.039 Uiso 1 1 calc R . . 
H15F H 0.3930 0.1082 0.0346 0.039 Uiso 1 1 calc R . . 
C16 C 0.3474(2) 0.3139(2) 0.18492(11) 0.0267(5) Uani 1 1 d . . . 
H16D H 0.2753 0.3680 0.2022 0.040 Uiso 1 1 calc R . . 
H16E H 0.4288 0.3610 0.1865 0.040 Uiso 1 1 calc R . . 
H16F H 0.3562 0.2527 0.2143 0.040 Uiso 1 1 calc R . . 
C17 C 0.0266(2) -0.14617(18) 0.07329(11) 0.0231(5) Uani 1 1 d . . . 
H17D H 0.0275 -0.1306 0.0256 0.035 Uiso 1 1 calc R . . 
H17E H -0.0166 -0.2243 0.0736 0.035 Uiso 1 1 calc R . . 
H17F H 0.1165 -0.1482 0.0903 0.035 Uiso 1 1 calc R . . 
C18 C -0.19319(19) -0.03973(18) 0.09517(11) 0.0215(4) Uani 1 1 d . . . 
H18D H -0.2383 0.0288 0.1237 0.032 Uiso 1 1 calc R . . 
H18E H -0.2386 -0.1154 0.0990 0.032 Uiso 1 1 calc R . . 
H18F H -0.1929 -0.0301 0.0463 0.032 Uiso 1 1 calc R . . 
S' S 0.73338(5) 0.60016(4) 0.39188(3) 0.01803(12) Uani 1 1 d . . . 
O1' O 0.61908(13) 0.73246(12) 0.16805(7) 0.0210(3) Uani 1 1 d . . . 
O2' O 0.57501(13) 0.52876(13) 0.12218(7) 0.0251(3) Uani 1 1 d . . . 
O3' O 0.79771(14) 0.27467(12) 0.14753(7) 0.0229(3) Uani 1 1 d . . . 
O4' O 0.71532(13) 0.65867(12) 0.33151(7) 0.0207(3) Uani 1 1 d . . . 
O5' O 0.65998(13) 0.64395(13) 0.45563(7) 0.0246(3) Uani 1 1 d . . . 
O6' O 1.14882(14) 0.60733(14) 0.45354(8) 0.0315(4) Uani 1 1 d . . . 
O7' O 1.21483(13) 0.54107(13) 0.34032(7) 0.0239(3) Uani 1 1 d . . . 
N1' N 0.78537(15) 0.60055(14) 0.15095(8) 0.0174(3) Uani 1 1 d . . . 
H1' H 0.8333 0.6646 0.1681 0.021 Uiso 1 1 calc R . . 
N2' N 0.74973(15) 0.43611(14) 0.23840(8) 0.0171(3) Uani 1 1 d . . . 
H2' H 0.7489 0.5156 0.2485 0.021 Uiso 1 1 calc R . . 
N3' N 0.88959(16) 0.61650(15) 0.41359(9) 0.0207(4) Uani 1 1 d . . . 
H3' H 0.9130 0.6412 0.4573 0.025 Uiso 1 1 calc R . . 
C1' C 0.65171(19) 0.61320(18) 0.14449(10) 0.0182(4) Uani 1 1 d . . . 
C2' C 0.84974(19) 0.48117(17) 0.12951(10) 0.0184(4) Uani 1 1 d . . . 
C3' C 0.79305(18) 0.38556(17) 0.17174(10) 0.0175(4) Uani 1 1 d . . . 
C4' C 0.70621(18) 0.37559(17) 0.29277(10) 0.0168(4) Uani 1 1 d . . . 
C5' C 0.67081(18) 0.25029(18) 0.27843(11) 0.0198(4) Uani 1 1 d . . . 
H5' H 0.6733 0.2063 0.2318 0.024 Uiso 1 1 calc R . . 
C6' C 0.63223(19) 0.19102(19) 0.33265(11) 0.0232(5) Uani 1 1 d . . . 
H6' H 0.6102 0.1072 0.3221 0.028 Uiso 1 1 calc R . . 
C7' C 0.6257(2) 0.25403(19) 0.40236(11) 0.0249(5) Uani 1 1 d . . . 
H7' H 0.6012 0.2127 0.4386 0.030 Uiso 1 1 calc R . . 
C8' C 0.65592(19) 0.3787(2) 0.41763(11) 0.0232(5) Uani 1 1 d . . . 
H8' H 0.6493 0.4222 0.4642 0.028 Uiso 1 1 calc R . . 
C9' C 0.69632(18) 0.44000(17) 0.36367(10) 0.0171(4) Uani 1 1 d . . . 
C10' C 0.99029(19) 0.58846(18) 0.35755(11) 0.0213(4) Uani 1 1 d . . . 
H10A H 0.9912 0.6524 0.3290 0.026 Uiso 1 1 calc R . . 
H10B H 0.9687 0.5102 0.3266 0.026 Uiso 1 1 calc R . . 
C11' C 1.1254(2) 0.58153(18) 0.39083(11) 0.0215(4) Uani 1 1 d . . . 
C12' C 1.3456(2) 0.5164(2) 0.36624(12) 0.0279(5) Uani 1 1 d . . . 
H12A H 1.3844 0.5919 0.3920 0.042 Uiso 1 1 calc R . . 
H12B H 1.4017 0.4833 0.3266 0.042 Uiso 1 1 calc R . . 
H12C H 1.3375 0.4577 0.3972 0.042 Uiso 1 1 calc R . . 
C13' C 0.47836(19) 0.7706(2) 0.17233(11) 0.0232(5) Uani 1 1 d . . . 
C14' C 0.4253(2) 0.7637(3) 0.09766(12) 0.0447(7) Uani 1 1 d . . . 
H14A H 0.4836 0.8095 0.0721 0.067 Uiso 1 1 calc R . . 
H14B H 0.3377 0.7985 0.0999 0.067 Uiso 1 1 calc R . . 
H14C H 0.4209 0.6789 0.0736 0.067 Uiso 1 1 calc R . . 
C15' C 0.4895(2) 0.90330(19) 0.21204(12) 0.0287(5) Uani 1 1 d . . . 
H15A H 0.5265 0.9049 0.2585 0.043 Uiso 1 1 calc R . . 
H15B H 0.4026 0.9396 0.2166 0.043 Uiso 1 1 calc R . . 
H15C H 0.5466 0.9495 0.1861 0.043 Uiso 1 1 calc R . . 
C16' C 0.3971(2) 0.6941(2) 0.21562(13) 0.0355(6) Uani 1 1 d . . . 
H16A H 0.3788 0.6139 0.1873 0.053 Uiso 1 1 calc R . . 
H16B H 0.3146 0.7350 0.2296 0.053 Uiso 1 1 calc R . . 
H16C H 0.4465 0.6852 0.2573 0.053 Uiso 1 1 calc R . . 
C17' C 0.8341(2) 0.43144(19) 0.04968(11) 0.0270(5) Uani 1 1 d . . . 
H17A H 0.7412 0.4186 0.0381 0.040 Uiso 1 1 calc R . . 
H17B H 0.8801 0.3544 0.0371 0.040 Uiso 1 1 calc R . . 
H17C H 0.8713 0.4901 0.0236 0.040 Uiso 1 1 calc R . . 
C18' C 0.99753(19) 0.49888(19) 0.14928(11) 0.0237(5) Uani 1 1 d . . . 
H18A H 1.0383 0.5535 0.1217 0.036 Uiso 1 1 calc R . . 
H18B H 1.0410 0.4203 0.1394 0.036 Uiso 1 1 calc R . . 
H18C H 1.0059 0.5340 0.1991 0.036 Uiso 1 1 calc R . . 
 
 
_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 
S O5 1.4324(14) . ? 
S O4 1.4349(14) . ? 
S N3 1.6105(16) . ? 
S C9 1.7672(18) . ? 
O1 C1 1.348(2) . ? 
O1 C13 1.492(2) . ? 
O2 C1 1.217(2) . ? 
O3 C3 1.228(2) . ? 
O6 C11 1.200(2) . ? 
O7 C11 1.341(2) . ? 
O7 C12 1.449(2) . ? 
N1 C1 1.357(2) . ? 
N1 C2 1.471(2) . ? 
N1 H1 0.8600 . ? 
N2 C3 1.353(2) . ? 
N2 C4 1.410(2) . ? 
N2 H2 0.8600 . ? 
N3 C10 1.448(2) . ? 
N3 H3 0.8600 . ? 
C2 C17 1.526(3) . ? 
C2 C18 1.533(3) . ? 
C2 C3 1.537(3) . ? 
C4 C5 1.390(3) . ? 
C4 C9 1.401(3) . ? 
C5 C6 1.385(3) . ? 
C5 H5 0.9300 . ? 
C6 C7 1.380(3) . ? 
C6 H6 0.9300 . ? 
C7 C8 1.384(3) . ? 
C7 H7 0.9300 . ? 
C8 C9 1.386(3) . ? 
C8 H8 0.9300 . ? 
C10 C11 1.505(3) . ? 
C10 H10C 0.9700 . ? 
C10 H10D 0.9700 . ? 
C12 H12D 0.9600 . ? 
C12 H12E 0.9600 . ? 
C12 H12F 0.9600 . ? 
C13 C16 1.515(3) . ? 
C13 C15 1.519(3) . ? 
C13 C14 1.522(3) . ? 
C14 H14D 0.9600 . ? 
C14 H14E 0.9600 . ? 
C14 H14F 0.9600 . ? 
C15 H15D 0.9600 . ? 
C15 H15E 0.9600 . ? 
C15 H15F 0.9600 . ? 
C16 H16D 0.9600 . ? 
C16 H16E 0.9600 . ? 
C16 H16F 0.9600 . ? 
C17 H17D 0.9600 . ? 
C17 H17E 0.9600 . ? 
C17 H17F 0.9600 . ? 
C18 H18D 0.9600 . ? 
C18 H18E 0.9600 . ? 
C18 H18F 0.9600 . ? 
S' O5' 1.4300(14) . ? 
S' O4' 1.4376(14) . ? 
S' N3' 1.6194(16) . ? 
S' C9' 1.7780(19) . ? 
O1' C1' 1.349(2) . ? 
O1' C13' 1.475(2) . ? 
O2' C1' 1.212(2) . ? 
O3' C3' 1.222(2) . ? 
O6' C11' 1.201(2) . ? 
O7' C11' 1.335(2) . ? 
O7' C12' 1.448(2) . ? 
N1' C1' 1.357(2) . ? 
N1' C2' 1.459(2) . ? 
N1' H1' 0.8600 . ? 
N2' C3' 1.363(2) . ? 
N2' C4' 1.405(2) . ? 
N2' H2' 0.8600 . ? 
N3' C10' 1.465(3) . ? 
N3' H3' 0.8600 . ? 
C2' C17' 1.528(3) . ? 
C2' C18' 1.530(3) . ? 
C2' C3' 1.548(3) . ? 
C4' C5' 1.396(3) . ? 
C4' C9' 1.409(3) . ? 
C5' C6' 1.380(3) . ? 
C5' H5' 0.9300 . ? 
C6' C7' 1.382(3) . ? 
C6' H6' 0.9300 . ? 
C7' C8' 1.378(3) . ? 
C7' H7' 0.9300 . ? 
C8' C9' 1.394(3) . ? 
C8' H8' 0.9300 . ? 
C10' C11' 1.505(3) . ? 
C10' H10A 0.9700 . ? 
C10' H10B 0.9700 . ? 
C12' H12A 0.9600 . ? 
C12' H12B 0.9600 . ? 
C12' H12C 0.9600 . ? 
C13' C14' 1.512(3) . ? 
C13' C15' 1.516(3) . ? 
C13' C16' 1.519(3) . ? 
C14' H14A 0.9600 . ? 
C14' H14B 0.9600 . ? 
C14' H14C 0.9600 . ? 
C15' H15A 0.9600 . ? 
C15' H15B 0.9600 . ? 
C15' H15C 0.9600 . ? 
C16' H16A 0.9600 . ? 
C16' H16B 0.9600 . ? 
C16' H16C 0.9600 . ? 
C17' H17A 0.9600 . ? 
C17' H17B 0.9600 . ? 
C17' H17C 0.9600 . ? 
C18' H18A 0.9600 . ? 
C18' H18B 0.9600 . ? 
C18' H18C 0.9600 . ? 
 
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 
O5 S O4 119.45(8) . . ? 
O5 S N3 107.48(9) . . ? 
O4 S N3 105.67(8) . . ? 
O5 S C9 107.26(9) . . ? 
O4 S C9 109.20(8) . . ? 
N3 S C9 107.20(8) . . ? 
C1 O1 C13 121.78(14) . . ? 
C11 O7 C12 116.09(16) . . ? 
C1 N1 C2 123.17(15) . . ? 
C1 N1 H1 118.4 . . ? 
C2 N1 H1 118.4 . . ? 
C3 N2 C4 126.51(16) . . ? 
C3 N2 H2 116.7 . . ? 
C4 N2 H2 116.7 . . ? 
C10 N3 S 120.58(14) . . ? 
C10 N3 H3 119.7 . . ? 
S N3 H3 119.7 . . ? 
O2 C1 O1 126.30(17) . . ? 
O2 C1 N1 123.96(17) . . ? 
O1 C1 N1 109.74(16) . . ? 
N1 C2 C17 111.15(15) . . ? 
N1 C2 C18 106.41(15) . . ? 
C17 C2 C18 109.99(16) . . ? 
N1 C2 C3 112.57(15) . . ? 
C17 C2 C3 109.62(15) . . ? 
C18 C2 C3 106.96(15) . . ? 
O3 C3 N2 124.03(17) . . ? 
O3 C3 C2 121.21(17) . . ? 
N2 C3 C2 114.60(15) . . ? 
C5 C4 C9 118.70(17) . . ? 
C5 C4 N2 121.81(17) . . ? 
C9 C4 N2 119.45(16) . . ? 
C6 C5 C4 119.75(18) . . ? 
C6 C5 H5 120.1 . . ? 
C4 C5 H5 120.1 . . ? 
C7 C6 C5 121.27(18) . . ? 
C7 C6 H6 119.4 . . ? 
C5 C6 H6 119.4 . . ? 
C6 C7 C8 119.62(18) . . ? 
C6 C7 H7 120.2 . . ? 
C8 C7 H7 120.2 . . ? 
C7 C8 C9 119.60(18) . . ? 
C7 C8 H8 120.2 . . ? 
C9 C8 H8 120.2 . . ? 
C8 C9 C4 121.04(17) . . ? 
C8 C9 S 117.77(14) . . ? 
C4 C9 S 121.13(14) . . ? 
N3 C10 C11 113.63(17) . . ? 
N3 C10 H10C 108.8 . . ? 
C11 C10 H10C 108.8 . . ? 
N3 C10 H10D 108.8 . . ? 
C11 C10 H10D 108.8 . . ? 
H10C C10 H10D 107.7 . . ? 
O6 C11 O7 124.79(19) . . ? 
O6 C11 C10 125.65(18) . . ? 
O7 C11 C10 109.56(17) . . ? 
O7 C12 H12D 109.5 . . ? 
O7 C12 H12E 109.5 . . ? 
H12D C12 H12E 109.5 . . ? 
O7 C12 H12F 109.5 . . ? 
H12D C12 H12F 109.5 . . ? 
H12E C12 H12F 109.5 . . ? 
O1 C13 C16 109.82(15) . . ? 
O1 C13 C15 110.79(15) . . ? 
C16 C13 C15 112.21(17) . . ? 
O1 C13 C14 101.88(14) . . ? 
C16 C13 C14 111.09(17) . . ? 
C15 C13 C14 110.59(16) . . ? 
C13 C14 H14D 109.5 . . ? 
C13 C14 H14E 109.5 . . ? 
H14D C14 H14E 109.5 . . ? 
C13 C14 H14F 109.5 . . ? 
H14D C14 H14F 109.5 . . ? 
H14E C14 H14F 109.5 . . ? 
C13 C15 H15D 109.5 . . ? 
C13 C15 H15E 109.5 . . ? 
H15D C15 H15E 109.5 . . ? 
C13 C15 H15F 109.5 . . ? 
H15D C15 H15F 109.5 . . ? 
H15E C15 H15F 109.5 . . ? 
C13 C16 H16D 109.5 . . ? 
C13 C16 H16E 109.5 . . ? 
H16D C16 H16E 109.5 . . ? 
C13 C16 H16F 109.5 . . ? 
H16D C16 H16F 109.5 . . ? 
H16E C16 H16F 109.5 . . ? 
C2 C17 H17D 109.5 . . ? 
C2 C17 H17E 109.5 . . ? 
H17D C17 H17E 109.5 . . ? 
C2 C17 H17F 109.5 . . ? 
H17D C17 H17F 109.5 . . ? 
H17E C17 H17F 109.5 . . ? 
C2 C18 H18D 109.5 . . ? 
C2 C18 H18E 109.5 . . ? 
H18D C18 H18E 109.5 . . ? 
C2 C18 H18F 109.5 . . ? 
H18D C18 H18F 109.5 . . ? 
H18E C18 H18F 109.5 . . ? 
O5' S' O4' 119.12(8) . . ? 
O5' S' N3' 106.25(8) . . ? 
O4' S' N3' 106.70(8) . . ? 
O5' S' C9' 108.05(9) . . ? 
O4' S' C9' 107.53(8) . . ? 
N3' S' C9' 108.88(9) . . ? 
C1' O1' C13' 120.74(15) . . ? 
C11' O7' C12' 115.11(16) . . ? 
C1' N1' C2' 121.67(16) . . ? 
C1' N1' H1' 119.2 . . ? 
C2' N1' H1' 119.2 . . ? 
C3' N2' C4' 128.61(16) . . ? 
C3' N2' H2' 115.7 . . ? 
C4' N2' H2' 115.7 . . ? 
C10' N3' S' 118.90(13) . . ? 
C10' N3' H3' 120.5 . . ? 
S' N3' H3' 120.5 . . ? 
O2' C1' O1' 126.24(18) . . ? 
O2' C1' N1' 124.41(18) . . ? 
O1' C1' N1' 109.33(16) . . ? 
N1' C2' C17' 111.63(16) . . ? 
N1' C2' C18' 107.64(15) . . ? 
C17' C2' C18' 110.24(16) . . ? 
N1' C2' C3' 110.91(15) . . ? 
C17' C2' C3' 109.66(16) . . ? 
C18' C2' C3' 106.62(15) . . ? 
O3' C3' N2' 124.79(17) . . ? 
O3' C3' C2' 120.96(17) . . ? 
N2' C3' C2' 114.03(16) . . ? 
C5' C4' N2' 121.29(17) . . ? 
C5' C4' C9' 117.87(17) . . ? 
N2' C4' C9' 120.83(16) . . ? 
C6' C5' C4' 120.71(19) . . ? 
C6' C5' H5' 119.6 . . ? 
C4' C5' H5' 119.6 . . ? 
C5' C6' C7' 121.13(19) . . ? 
C5' C6' H6' 119.4 . . ? 
C7' C6' H6' 119.4 . . ? 
C8' C7' C6' 119.31(18) . . ? 
C8' C7' H7' 120.3 . . ? 
C6' C7' H7' 120.3 . . ? 
C7' C8' C9' 120.40(19) . . ? 
C7' C8' H8' 119.8 . . ? 
C9' C8' H8' 119.8 . . ? 
C8' C9' C4' 120.51(18) . . ? 
C8' C9' S' 115.10(15) . . ? 
C4' C9' S' 124.39(14) . . ? 
N3' C10' C11' 109.54(16) . . ? 
N3' C10' H10A 109.8 . . ? 
C11' C10' H10A 109.8 . . ? 
N3' C10' H10B 109.8 . . ? 
C11' C10' H10B 109.8 . . ? 
H10A C10' H10B 108.2 . . ? 
O6' C11' O7' 125.12(18) . . ? 
O6' C11' C10' 125.02(19) . . ? 
O7' C11' C10' 109.86(17) . . ? 
O7' C12' H12A 109.5 . . ? 
O7' C12' H12B 109.5 . . ? 
H12A C12' H12B 109.5 . . ? 
O7' C12' H12C 109.5 . . ? 
H12A C12' H12C 109.5 . . ? 
H12B C12' H12C 109.5 . . ? 
O1' C13' C14' 108.80(16) . . ? 
O1' C13' C15' 101.81(15) . . ? 
C14' C13' C15' 111.38(19) . . ? 
O1' C13' C16' 110.97(16) . . ? 
C14' C13' C16' 113.3(2) . . ? 
C15' C13' C16' 109.98(17) . . ? 
C13' C14' H14A 109.5 . . ? 
C13' C14' H14B 109.5 . . ? 
H14A C14' H14B 109.5 . . ? 
C13' C14' H14C 109.5 . . ? 
H14A C14' H14C 109.5 . . ? 
H14B C14' H14C 109.5 . . ? 
C13' C15' H15A 109.5 . . ? 
C13' C15' H15B 109.5 . . ? 
H15A C15' H15B 109.5 . . ? 
C13' C15' H15C 109.5 . . ? 
H15A C15' H15C 109.5 . . ? 
H15B C15' H15C 109.5 . . ? 
C13' C16' H16A 109.5 . . ? 
C13' C16' H16B 109.5 . . ? 
H16A C16' H16B 109.5 . . ? 
C13' C16' H16C 109.5 . . ? 
H16A C16' H16C 109.5 . . ? 
H16B C16' H16C 109.5 . . ? 
C2' C17' H17A 109.5 . . ? 
C2' C17' H17B 109.5 . . ? 
H17A C17' H17B 109.5 . . ? 
C2' C17' H17C 109.5 . . ? 
H17A C17' H17C 109.5 . . ? 
H17B C17' H17C 109.5 . . ? 
C2' C18' H18A 109.5 . . ? 
C2' C18' H18B 109.5 . . ? 
H18A C18' H18B 109.5 . . ? 
C2' C18' H18C 109.5 . . ? 
H18A C18' H18C 109.5 . . ? 
H18B C18' H18C 109.5 . . ? 
 
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 
O5 S N3 C10 42.42(16) . . . . ? 
O4 S N3 C10 171.01(14) . . . . ? 
C9 S N3 C10 -72.61(16) . . . . ? 
C13 O1 C1 O2 0.5(3) . . . . ? 
C13 O1 C1 N1 -179.25(15) . . . . ? 
C2 N1 C1 O2 -23.7(3) . . . . ? 
C2 N1 C1 O1 156.08(16) . . . . ? 
C1 N1 C2 C17 -54.7(2) . . . . ? 
C1 N1 C2 C18 -174.41(16) . . . . ? 
C1 N1 C2 C3 68.7(2) . . . . ? 
C4 N2 C3 O3 -1.1(3) . . . . ? 
C4 N2 C3 C2 174.35(16) . . . . ? 
N1 C2 C3 O3 -153.28(17) . . . . ? 
C17 C2 C3 O3 -29.0(2) . . . . ? 
C18 C2 C3 O3 90.2(2) . . . . ? 
N1 C2 C3 N2 31.1(2) . . . . ? 
C17 C2 C3 N2 155.38(16) . . . . ? 
C18 C2 C3 N2 -85.40(18) . . . . ? 
C3 N2 C4 C5 -34.3(3) . . . . ? 
C3 N2 C4 C9 148.14(18) . . . . ? 
C9 C4 C5 C6 0.3(3) . . . . ? 
N2 C4 C5 C6 -177.27(17) . . . . ? 
C4 C5 C6 C7 0.5(3) . . . . ? 
C5 C6 C7 C8 -0.5(3) . . . . ? 
C6 C7 C8 C9 -0.3(3) . . . . ? 
C7 C8 C9 C4 1.0(3) . . . . ? 
C7 C8 C9 S -176.10(15) . . . . ? 
C5 C4 C9 C8 -1.0(3) . . . . ? 
N2 C4 C9 C8 176.57(17) . . . . ? 
C5 C4 C9 S 176.00(14) . . . . ? 
N2 C4 C9 S -6.4(2) . . . . ? 
O5 S C9 C8 -8.66(17) . . . . ? 
O4 S C9 C8 -139.46(15) . . . . ? 
N3 S C9 C8 106.51(16) . . . . ? 
O5 S C9 C4 174.22(15) . . . . ? 
O4 S C9 C4 43.42(18) . . . . ? 
N3 S C9 C4 -70.61(17) . . . . ? 
S N3 C10 C11 108.33(18) . . . . ? 
C12 O7 C11 O6 1.4(3) . . . . ? 
C12 O7 C11 C10 -178.38(16) . . . . ? 
N3 C10 C11 O6 -10.0(3) . . . . ? 
N3 C10 C11 O7 169.74(16) . . . . ? 
C1 O1 C13 C16 -68.0(2) . . . . ? 
C1 O1 C13 C15 56.5(2) . . . . ? 
C1 O1 C13 C14 174.21(16) . . . . ? 
O5' S' N3' C10' -175.10(14) . . . . ? 
O4' S' N3' C10' -47.03(16) . . . . ? 
C9' S' N3' C10' 68.75(16) . . . . ? 
C13' O1' C1' O2' 3.5(3) . . . . ? 
C13' O1' C1' N1' -175.18(15) . . . . ? 
C2' N1' C1' O2' 1.3(3) . . . . ? 
C2' N1' C1' O1' -179.96(15) . . . . ? 
C1' N1' C2' C17' 63.1(2) . . . . ? 
C1' N1' C2' C18' -175.77(16) . . . . ? 
C1' N1' C2' C3' -59.5(2) . . . . ? 
C4' N2' C3' O3' 1.9(3) . . . . ? 
C4' N2' C3' C2' -172.76(16) . . . . ? 
N1' C2' C3' O3' 155.25(17) . . . . ? 
C17' C2' C3' O3' 31.5(2) . . . . ? 
C18' C2' C3' O3' -87.8(2) . . . . ? 
N1' C2' C3' N2' -29.8(2) . . . . ? 
C17' C2' C3' N2' -153.58(16) . . . . ? 
C18' C2' C3' N2' 87.08(19) . . . . ? 
C3' N2' C4' C5' -16.2(3) . . . . ? 
C3' N2' C4' C9' 164.08(18) . . . . ? 
N2' C4' C5' C6' 177.95(17) . . . . ? 
C9' C4' C5' C6' -2.4(3) . . . . ? 
C4' C5' C6' C7' 0.9(3) . . . . ? 
C5' C6' C7' C8' 1.2(3) . . . . ? 
C6' C7' C8' C9' -1.8(3) . . . . ? 
C7' C8' C9' C4' 0.3(3) . . . . ? 
C7' C8' C9' S' -179.38(15) . . . . ? 
C5' C4' C9' C8' 1.8(3) . . . . ? 
N2' C4' C9' C8' -178.55(17) . . . . ? 
C5' C4' C9' S' -178.58(14) . . . . ? 
N2' C4' C9' S' 1.1(3) . . . . ? 
O5' S' C9' C8' -25.36(17) . . . . ? 
O4' S' C9' C8' -155.14(14) . . . . ? 
N3' S' C9' C8' 89.62(16) . . . . ? 
O5' S' C9' C4' 154.95(15) . . . . ? 
O4' S' C9' C4' 25.18(18) . . . . ? 
N3' S' C9' C4' -90.06(17) . . . . ? 
S' N3' C10' C11' -167.08(13) . . . . ? 
C12' O7' C11' O6' 6.3(3) . . . . ? 
C12' O7' C11' C10' -173.02(16) . . . . ? 
N3' C10' C11' O6' -6.9(3) . . . . ? 
N3' C10' C11' O7' 172.34(15) . . . . ? 
C1' O1' C13' C14' -71.3(2) . . . . ? 
C1' O1' C13' C15' 171.01(16) . . . . ? 
C1' O1' C13' C16' 54.0(2) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.576 
_refine_diff_density_min   -0.519 
_refine_diff_density_rms    0.048 
