# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_LWD_01_1_0m_P21c
_database_code_depnum_ccdc_archive 'CCDC 1996070'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-04-09 deposited with the CCDC.	2020-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 N2 O3 S'
_chemical_formula_weight         358.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.0085(11)
_cell_length_b                   9.8960(7)
_cell_length_c                   10.5439(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.8684(19)
_cell_angle_gamma                90
_cell_volume                     1772.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9247
_cell_measurement_theta_min      2.6011
_cell_measurement_theta_max      80.7559

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.794
_shelx_estimated_absorpt_T_min   0.624
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6101
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.
(2015). J. Appl. Cryst. 48 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51780
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.601
_diffrn_reflns_theta_max         80.855
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3868
_reflns_number_gt                3608
_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       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev937 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The tetrahydrofuran ring is disordered by envelope inversion, with the 
oxygen flap up or down. The disorder extends to the whole ring and the 
adjacent phenyl substituent. The two disordered moieties were restrained 
to have similar geometries. Uij components of ADPs for disordered atoms 
closer to each other than 2.0 Angstrom were restrained to be similar. 
Subject to these conditions the occupancy ratio refined to 0.749(5) to 
0.251(5). 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0621P)²+0.5372P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0094(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3868
_refine_ls_number_parameters     324
_refine_ls_number_restraints     382
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_restrained_S_all      1.160
_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
C11 C 0.33333(9) 0.74274(17) 0.36722(15) 0.0327(3) Uani 1 1 d . . . . .
C12 C 0.33029(11) 0.8340(2) 0.25383(16) 0.0430(4) Uani 1 1 d . . . . .
H12A H 0.383967 0.853932 0.229713 0.064 Uiso 1 1 calc R U . . .
H12B H 0.303661 0.918371 0.274603 0.064 Uiso 1 1 calc R U . . .
H12C H 0.301251 0.789384 0.182944 0.064 Uiso 1 1 calc R U . . .
C13 C 0.11408(8) 0.55761(15) 0.46345(14) 0.0291(3) Uani 1 1 d . . . . .
C14 C 0.15088(10) 0.47213(16) 0.55192(15) 0.0359(4) Uani 1 1 d . . . . .
H14 H 0.181549 0.507994 0.621803 0.043 Uiso 1 1 calc R U . . .
C15 C 0.14243(10) 0.33422(17) 0.53727(17) 0.0395(4) Uani 1 1 d . . . . .
H15 H 0.167493 0.275487 0.598019 0.047 Uiso 1 1 calc R U . . .
C16 C 0.09802(10) 0.27929(16) 0.43551(17) 0.0356(4) Uani 1 1 d . . . . .
C17 C 0.06101(10) 0.36703(18) 0.34865(17) 0.0390(4) Uani 1 1 d . . . . .
H17 H 0.029934 0.331232 0.279196 0.047 Uiso 1 1 calc R U . . .
C18 C 0.06865(9) 0.50571(16) 0.36158(16) 0.0348(3) Uani 1 1 d . . . . .
H18 H 0.043142 0.564686 0.301518 0.042 Uiso 1 1 calc R U . . .
C19 C 0.09135(12) 0.12848(18) 0.4197(2) 0.0484(5) Uani 1 1 d . . . . .
H19A H 0.130391 0.083895 0.477026 0.073 Uiso 0.60(3) 1 calc R U P . .
H19B H 0.100918 0.104124 0.331743 0.073 Uiso 0.60(3) 1 calc R U P . .
H19C H 0.038406 0.099251 0.440155 0.073 Uiso 0.60(3) 1 calc R U P . .
H19D H 0.049419 0.107618 0.355590 0.073 Uiso 0.40(3) 1 calc R U P . .
H19E H 0.078892 0.087390 0.500873 0.073 Uiso 0.40(3) 1 calc R U P . .
H19F H 0.141404 0.092262 0.392461 0.073 Uiso 0.40(3) 1 calc R U P . .
N1 N 0.27348(7) 0.71307(13) 0.43169(12) 0.0309(3) Uani 1 1 d . . . . .
N2 N 0.20212(8) 0.77431(13) 0.38912(13) 0.0299(3) Uani 1 1 d D . . . .
H2N H 0.1911(12) 0.770(2) 0.3085(15) 0.036 Uiso 1 1 d D U . . .
O1 O 0.52915(9) 0.58488(17) 0.3621(2) 0.0396(6) Uani 0.749(5) 1 d D U P A 1
C1 C 0.4499(3) 0.5947(7) 0.3146(8) 0.0385(10) Uani 0.749(5) 1 d D U P A 1
H1A H 0.425387 0.504113 0.306404 0.046 Uiso 0.749(5) 1 calc R U P A 1
H1B H 0.446515 0.639748 0.230691 0.046 Uiso 0.749(5) 1 calc R U P A 1
C2 C 0.40988(9) 0.6794(2) 0.41381(15) 0.0382(4) Uani 0.749(5) 1 d D U P A 1
H2 H 0.402044 0.624394 0.491740 0.046 Uiso 0.749(5) 1 calc R U P A 1
C3 C 0.4745(2) 0.7874(4) 0.4409(4) 0.0368(9) Uani 0.749(5) 1 d D U P A 1
H3A H 0.472653 0.858682 0.374947 0.044 Uiso 0.749(5) 1 calc R U P A 1
H3B H 0.469463 0.829663 0.525245 0.044 Uiso 0.749(5) 1 calc R U P A 1
C4 C 0.5507(2) 0.7030(4) 0.4369(3) 0.0349(7) Uani 0.749(5) 1 d D U P A 1
H4 H 0.567164 0.673980 0.525157 0.042 Uiso 0.749(5) 1 calc R U P A 1
C5 C 0.6172(4) 0.7798(7) 0.3814(5) 0.0291(9) Uani 0.749(5) 1 d D U P A 1
C6 C 0.6489(3) 0.8949(7) 0.4420(7) 0.0350(10) Uani 0.749(5) 1 d D U P A 1
H6 H 0.629225 0.923082 0.520436 0.042 Uiso 0.749(5) 1 calc R U P A 1
C7 C 0.7088(3) 0.9688(6) 0.3893(4) 0.0392(11) Uani 0.749(5) 1 d D U P A 1
H7 H 0.728913 1.047516 0.431018 0.047 Uiso 0.749(5) 1 calc R U P A 1
C8 C 0.7390(2) 0.9278(4) 0.2768(4) 0.0402(9) Uani 0.749(5) 1 d D U P A 1
H8 H 0.780248 0.977530 0.241110 0.048 Uiso 0.749(5) 1 calc R U P A 1
C9 C 0.7086(2) 0.8133(4) 0.2160(4) 0.0392(8) Uani 0.749(5) 1 d D U P A 1
H9 H 0.729105 0.784992 0.138129 0.047 Uiso 0.749(5) 1 calc R U P A 1
C10 C 0.6483(3) 0.7395(5) 0.2684(5) 0.0348(9) Uani 0.749(5) 1 d D U P A 1
H10 H 0.628381 0.660961 0.226222 0.042 Uiso 0.749(5) 1 calc R U P A 1
O1B O 0.5224(3) 0.6297(6) 0.2840(6) 0.0418(15) Uani 0.251(5) 1 d D U P A 2
C1B C 0.4458(9) 0.580(2) 0.319(2) 0.042(2) Uani 0.251(5) 1 d D U P A 2
H1C H 0.451544 0.489817 0.358102 0.050 Uiso 0.251(5) 1 calc R U P A 2
H1D H 0.410253 0.572256 0.241963 0.050 Uiso 0.251(5) 1 calc R U P A 2
C2B C 0.40988(9) 0.6794(2) 0.41381(15) 0.0382(4) Uani 0.251(5) 1 d D U P A 2
H2B H 0.395720 0.621381 0.486904 0.046 Uiso 0.251(5) 1 calc R U P A 2
C3B C 0.4827(7) 0.7573(13) 0.4626(12) 0.039(2) Uani 0.251(5) 1 d D U P A 2
H3C H 0.489559 0.749821 0.556102 0.047 Uiso 0.251(5) 1 calc R U P A 2
H3D H 0.477999 0.853993 0.439488 0.047 Uiso 0.251(5) 1 calc R U P A 2
C4B C 0.5523(6) 0.6927(13) 0.3989(10) 0.0349(18) Uani 0.251(5) 1 d D U P A 2
H4B H 0.574942 0.620809 0.456524 0.042 Uiso 0.251(5) 1 calc R U P A 2
C5B C 0.6180(12) 0.785(2) 0.3639(18) 0.030(2) Uani 0.251(5) 1 d D U P A 2
C6B C 0.6343(12) 0.895(2) 0.444(2) 0.033(2) Uani 0.251(5) 1 d D U P A 2
H6B H 0.602140 0.913982 0.513370 0.040 Uiso 0.251(5) 1 calc R U P A 2
C7B C 0.6982(11) 0.976(2) 0.4214(15) 0.038(2) Uani 0.251(5) 1 d D U P A 2
H7B H 0.713989 1.043611 0.480968 0.045 Uiso 0.251(5) 1 calc R U P A 2
C8B C 0.7391(9) 0.9590(14) 0.3143(14) 0.039(2) Uani 0.251(5) 1 d D U P A 2
H8B H 0.779939 1.020667 0.296570 0.047 Uiso 0.251(5) 1 calc R U P A 2
C9B C 0.7225(7) 0.8566(13) 0.2335(11) 0.036(2) Uani 0.251(5) 1 d D U P A 2
H9B H 0.751530 0.845986 0.159474 0.043 Uiso 0.251(5) 1 calc R U P A 2
C10B C 0.6621(9) 0.7656(15) 0.2588(15) 0.030(2) Uani 0.251(5) 1 d D U P A 2
H10B H 0.651529 0.690743 0.204116 0.036 Uiso 0.251(5) 1 calc R U P A 2
O2 O 0.15061(7) 0.76548(11) 0.60445(11) 0.0337(3) Uani 1 1 d . . . . .
O3 O 0.06174(6) 0.80003(11) 0.41297(11) 0.0360(3) Uani 1 1 d . . . . .
S1 S 0.12715(2) 0.73328(4) 0.47536(3) 0.02781(15) 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
C11 N1 1.286(2) . ?
C11 C12 1.497(2) . ?
C11 C2B 1.505(2) . ?
C11 C2 1.505(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.385(2) . ?
C13 C18 1.390(2) . ?
C13 S1 1.7563(15) . ?
C14 C15 1.380(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(2) . ?
C16 C19 1.505(2) . ?
C17 C18 1.385(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 H19D 0.9800 . ?
C19 H19E 0.9800 . ?
C19 H19F 0.9800 . ?
N1 N2 1.4097(18) . ?
N2 S1 1.6533(14) . ?
N2 H2N 0.862(15) . ?
O1 C1 1.418(7) . ?
O1 C4 1.448(4) . ?
C1 C2 1.527(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.550(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.544(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.505(5) . ?
C4 H4 1.0000 . ?
C5 C10 1.386(5) . ?
C5 C6 1.401(5) . ?
C6 C7 1.392(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.376(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
O1B C4B 1.433(10) . ?
O1B C1B 1.456(15) . ?
C1B C2B 1.548(14) . ?
C1B H1C 0.9900 . ?
C1B H1D 0.9900 . ?
C2B C3B 1.526(12) . ?
C2B H2B 1.0000 . ?
C3B C4B 1.529(13) . ?
C3B H3C 0.9900 . ?
C3B H3D 0.9900 . ?
C4B C5B 1.505(12) . ?
C4B H4B 1.0000 . ?
C5B C10B 1.383(13) . ?
C5B C6B 1.400(14) . ?
C6B C7B 1.377(14) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.367(12) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.345(11) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.402(12) . ?
C9B H9B 0.9500 . ?
C10B H10B 0.9500 . ?
O2 S1 1.4349(11) . ?
O3 S1 1.4261(11) . ?

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
N1 C11 C12 124.28(15) . . ?
N1 C11 C2B 115.28(14) . . ?
C12 C11 C2B 120.44(14) . . ?
N1 C11 C2 115.28(14) . . ?
C12 C11 C2 120.44(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 120.65(14) . . ?
C14 C13 S1 120.32(12) . . ?
C18 C13 S1 118.99(12) . . ?
C15 C14 C13 119.17(15) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 121.47(16) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 118.33(15) . . ?
C17 C16 C19 121.17(16) . . ?
C15 C16 C19 120.50(16) . . ?
C18 C17 C16 121.15(15) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C13 119.22(15) . . ?
C17 C18 H18 120.4 . . ?
C13 C18 H18 120.4 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C19 H19D 109.5 . . ?
H19A C19 H19D 141.1 . . ?
H19B C19 H19D 56.3 . . ?
H19C C19 H19D 56.3 . . ?
C16 C19 H19E 109.5 . . ?
H19A C19 H19E 56.3 . . ?
H19B C19 H19E 141.1 . . ?
H19C C19 H19E 56.3 . . ?
H19D C19 H19E 109.5 . . ?
C16 C19 H19F 109.5 . . ?
H19A C19 H19F 56.3 . . ?
H19B C19 H19F 56.3 . . ?
H19C C19 H19F 141.1 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 109.5 . . ?
C11 N1 N2 115.16(13) . . ?
N1 N2 S1 113.25(10) . . ?
N1 N2 H2N 115.9(14) . . ?
S1 N2 H2N 113.3(14) . . ?
C1 O1 C4 110.4(3) . . ?
O1 C1 C2 104.1(4) . . ?
O1 C1 H1A 110.9 . . ?
C2 C1 H1A 110.9 . . ?
O1 C1 H1B 110.9 . . ?
C2 C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
C11 C2 C1 114.4(3) . . ?
C11 C2 C3 111.54(19) . . ?
C1 C2 C3 99.7(2) . . ?
C11 C2 H2 110.3 . . ?
C1 C2 H2 110.3 . . ?
C3 C2 H2 110.3 . . ?
C4 C3 C2 102.2(3) . . ?
C4 C3 H3A 111.3 . . ?
C2 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
O1 C4 C5 111.7(3) . . ?
O1 C4 C3 105.2(3) . . ?
C5 C4 C3 112.7(4) . . ?
O1 C4 H4 109.0 . . ?
C5 C4 H4 109.0 . . ?
C3 C4 H4 109.0 . . ?
C10 C5 C6 118.1(4) . . ?
C10 C5 C4 121.1(4) . . ?
C6 C5 C4 120.9(4) . . ?
C7 C6 C5 121.2(5) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C6 120.1(4) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 119.5(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C10 120.5(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C5 C10 C9 120.6(4) . . ?
C5 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C4B O1B C1B 102.5(9) . . ?
O1B C1B C2B 109.8(10) . . ?
O1B C1B H1C 109.7 . . ?
C2B C1B H1C 109.7 . . ?
O1B C1B H1D 109.7 . . ?
C2B C1B H1D 109.7 . . ?
H1C C1B H1D 108.2 . . ?
C11 C2B C3B 125.0(5) . . ?
C11 C2B C1B 114.5(10) . . ?
C3B C2B C1B 101.4(7) . . ?
C11 C2B H2B 104.7 . . ?
C3B C2B H2B 104.7 . . ?
C1B C2B H2B 104.7 . . ?
C2B C3B C4B 105.9(9) . . ?
C2B C3B H3C 110.6 . . ?
C4B C3B H3C 110.6 . . ?
C2B C3B H3D 110.6 . . ?
C4B C3B H3D 110.6 . . ?
H3C C3B H3D 108.7 . . ?
O1B C4B C5B 107.1(9) . . ?
O1B C4B C3B 107.7(9) . . ?
C5B C4B C3B 117.0(12) . . ?
O1B C4B H4B 108.3 . . ?
C5B C4B H4B 108.3 . . ?
C3B C4B H4B 108.3 . . ?
C10B C5B C6B 119.8(12) . . ?
C10B C5B C4B 123.4(12) . . ?
C6B C5B C4B 116.9(12) . . ?
C7B C6B C5B 118.5(14) . . ?
C7B C6B H6B 120.8 . . ?
C5B C6B H6B 120.8 . . ?
C8B C7B C6B 121.0(15) . . ?
C8B C7B H7B 119.5 . . ?
C6B C7B H7B 119.5 . . ?
C9B C8B C7B 121.0(13) . . ?
C9B C8B H8B 119.5 . . ?
C7B C8B H8B 119.5 . . ?
C8B C9B C10B 119.8(12) . . ?
C8B C9B H9B 120.1 . . ?
C10B C9B H9B 120.1 . . ?
C5B C10B C9B 119.6(11) . . ?
C5B C10B H10B 120.2 . . ?
C9B C10B H10B 120.2 . . ?
O3 S1 O2 120.55(7) . . ?
O3 S1 N2 103.76(7) . . ?
O2 S1 N2 106.36(7) . . ?
O3 S1 C13 109.41(7) . . ?
O2 S1 C13 108.41(7) . . ?
N2 S1 C13 107.59(7) . . ?

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
C18 C13 C14 C15 0.5(3) . . . . ?
S1 C13 C14 C15 -177.18(13) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C14 C15 C16 C19 178.44(17) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C19 C16 C17 C18 -178.49(17) . . . . ?
C16 C17 C18 C13 -0.1(3) . . . . ?
C14 C13 C18 C17 -0.5(2) . . . . ?
S1 C13 C18 C17 177.16(13) . . . . ?
C12 C11 N1 N2 -0.6(2) . . . . ?
C2B C11 N1 N2 178.99(13) . . . . ?
C2 C11 N1 N2 178.99(13) . . . . ?
C11 N1 N2 S1 -179.83(11) . . . . ?
C4 O1 C1 C2 -29.3(6) . . . . ?
N1 C11 C2 C1 123.3(3) . . . . ?
C12 C11 C2 C1 -57.1(4) . . . . ?
N1 C11 C2 C3 -124.5(2) . . . . ?
C12 C11 C2 C3 55.1(2) . . . . ?
O1 C1 C2 C11 160.9(4) . . . . ?
O1 C1 C2 C3 41.8(5) . . . . ?
C11 C2 C3 C4 -159.6(2) . . . . ?
C1 C2 C3 C4 -38.5(5) . . . . ?
C1 O1 C4 C5 -118.8(5) . . . . ?
C1 O1 C4 C3 3.8(5) . . . . ?
C2 C3 C4 O1 22.6(3) . . . . ?
C2 C3 C4 C5 144.6(3) . . . . ?
O1 C4 C5 C10 2.9(8) . . . . ?
C3 C4 C5 C10 -115.2(6) . . . . ?
O1 C4 C5 C6 -177.7(6) . . . . ?
C3 C4 C5 C6 64.2(8) . . . . ?
C10 C5 C6 C7 1.3(11) . . . . ?
C4 C5 C6 C7 -178.1(6) . . . . ?
C5 C6 C7 C8 -1.2(10) . . . . ?
C6 C7 C8 C9 0.6(7) . . . . ?
C7 C8 C9 C10 -0.3(6) . . . . ?
C6 C5 C10 C9 -1.0(10) . . . . ?
C4 C5 C10 C9 178.4(5) . . . . ?
C8 C9 C10 C5 0.5(8) . . . . ?
C4B O1B C1B C2B 34(2) . . . . ?
N1 C11 C2B C3B -117.6(6) . . . . ?
C12 C11 C2B C3B 62.0(6) . . . . ?
N1 C11 C2B C1B 116.6(10) . . . . ?
C12 C11 C2B C1B -63.8(10) . . . . ?
O1B C1B C2B C11 118.5(15) . . . . ?
O1B C1B C2B C3B -19(2) . . . . ?
C11 C2B C3B C4B -134.2(7) . . . . ?
C1B C2B C3B C4B -3.0(16) . . . . ?
C1B O1B C4B C5B -161.9(17) . . . . ?
C1B O1B C4B C3B -35.4(15) . . . . ?
C2B C3B C4B O1B 24.3(12) . . . . ?
C2B C3B C4B C5B 144.8(12) . . . . ?
O1B C4B C5B C10B -26(3) . . . . ?
C3B C4B C5B C10B -147(2) . . . . ?
O1B C4B C5B C6B 155(2) . . . . ?
C3B C4B C5B C6B 34(3) . . . . ?
C10B C5B C6B C7B -5(4) . . . . ?
C4B C5B C6B C7B 175(2) . . . . ?
C5B C6B C7B C8B 8(3) . . . . ?
C6B C7B C8B C9B -6(3) . . . . ?
C7B C8B C9B C10B 0(2) . . . . ?
C6B C5B C10B C9B 0(3) . . . . ?
C4B C5B C10B C9B -179.7(18) . . . . ?
C8B C9B C10B C5B 3(2) . . . . ?
N1 N2 S1 O3 -177.38(10) . . . . ?
N1 N2 S1 O2 54.51(12) . . . . ?
N1 N2 S1 C13 -61.49(12) . . . . ?
C14 C13 S1 O3 -155.61(13) . . . . ?
C18 C13 S1 O3 26.68(15) . . . . ?
C14 C13 S1 O2 -22.35(15) . . . . ?
C18 C13 S1 O2 159.94(12) . . . . ?
C14 C13 S1 N2 92.29(14) . . . . ?
C18 C13 S1 N2 -85.42(13) . . . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.051

