# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cu_20180905A_0m
_audit_block_doi                 10.5517/ccdc.csd.cc210g1l
_database_code_depnum_ccdc_archive 'CCDC 1877268'
_audit_update_record             
;
2018-11-07 deposited with the CCDC.
2019-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 N2 S'
_chemical_formula_weight         304.40

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'
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/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                   8.5086(4)
_cell_length_b                   17.1346(8)
_cell_length_c                   22.5907(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.192(2)
_cell_angle_gamma                90
_cell_volume                     3251.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    9852
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      66.57

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_exptl_absorpt_coefficient_mu    1.731
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67074
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.253
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_full        66.593
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             5659
_reflns_number_gt                5101
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+0.6077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0153(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5659
_refine_ls_number_parameters     437
_refine_ls_number_restraints     492
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      0.987
_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
C1A C 0.6813(6) 0.3444(2) 0.4539(2) 0.0849(13) Uani 0.642(7) 1 d . U P A 1
C2A C 0.6409(4) 0.3957(2) 0.40219(15) 0.0734(10) Uani 0.642(7) 1 d . U P A 1
H2A1 H 0.605962 0.364395 0.366744 0.088 Uiso 0.642(7) 1 calc R U P A 1
H2A2 H 0.735019 0.424363 0.395783 0.088 Uiso 0.642(7) 1 calc R U P A 1
C3A C 0.5104(4) 0.4529(2) 0.41092(14) 0.0715(11) Uani 0.642(7) 1 d . U P A 1
H3A1 H 0.536236 0.478297 0.449637 0.086 Uiso 0.642(7) 1 calc R U P A 1
H3A2 H 0.410143 0.425561 0.409633 0.086 Uiso 0.642(7) 1 calc R U P A 1
N1A N 0.7174(14) 0.3030(8) 0.4948(6) 0.112(3) Uani 0.642(7) 1 d . U P A 1
C3B C 0.6016(7) 0.4363(4) 0.3895(3) 0.0683(17) Uani 0.358(7) 1 d . U P A 2
H3B1 H 0.611582 0.396554 0.359725 0.082 Uiso 0.358(7) 1 calc R U P A 2
H3B2 H 0.707676 0.451132 0.408542 0.082 Uiso 0.358(7) 1 calc R U P A 2
C1B C 0.6024(14) 0.3509(6) 0.4744(4) 0.095(3) Uani 0.358(7) 1 d . U P A 2
C2B C 0.5101(8) 0.4046(5) 0.4353(3) 0.094(2) Uani 0.358(7) 1 d . U P A 2
H2B1 H 0.477130 0.447383 0.458648 0.112 Uiso 0.358(7) 1 calc R U P A 2
H2B2 H 0.415027 0.378669 0.415232 0.112 Uiso 0.358(7) 1 calc R U P A 2
N1B N 0.666(3) 0.3150(16) 0.5039(12) 0.124(6) Uani 0.358(7) 1 d . U P A 2
C4 C 0.37119(18) 0.47725(9) 0.29207(7) 0.0593(4) Uani 1 1 d . U . . .
C5 C 0.30570(18) 0.52545(9) 0.24362(7) 0.0577(4) Uani 1 1 d . U . . .
H5 H 0.331148 0.578251 0.244017 0.069 Uiso 1 1 calc R U . . .
C6 C 0.20547(16) 0.49481(8) 0.19636(7) 0.0512(3) Uani 1 1 d . U . . .
C7 C 0.16835(16) 0.41334(8) 0.19799(6) 0.0512(3) Uani 1 1 d . U . . .
C8 C 0.24599(17) 0.36961(9) 0.24722(7) 0.0552(3) Uani 1 1 d . U . . .
C9 C 0.2194(2) 0.28841(10) 0.24806(8) 0.0718(5) Uani 1 1 d . U . . .
H9 H 0.272031 0.258309 0.279340 0.086 Uiso 1 1 calc R U . . .
C10 C 0.1170(2) 0.25400(10) 0.20326(9) 0.0787(5) Uani 1 1 d . U . . .
H10 H 0.102746 0.200229 0.204277 0.094 Uiso 1 1 calc R U . . .
C11 C 0.03229(19) 0.29652(9) 0.15568(8) 0.0669(4) Uani 1 1 d . U . . .
C12 C 0.05966(17) 0.37518(9) 0.15384(7) 0.0578(4) Uani 1 1 d . U . . .
H12 H 0.004727 0.404315 0.122437 0.069 Uiso 1 1 calc R U . . .
C13 C -0.0855(3) 0.25665(12) 0.10878(10) 0.0926(6) Uani 1 1 d . U . . .
H13A H -0.143557 0.295146 0.083204 0.139 Uiso 1 1 calc R U . . .
H13B H -0.158261 0.226508 0.127876 0.139 Uiso 1 1 calc R U . . .
H13C H -0.029992 0.222813 0.085261 0.139 Uiso 1 1 calc R U . . .
C14 C 0.13862(16) 0.54541(8) 0.14500(7) 0.0525(3) Uani 1 1 d . U . . .
C15 C 0.05627(19) 0.61237(9) 0.15514(8) 0.0638(4) Uani 1 1 d . U . . .
H15 H 0.045288 0.625841 0.194154 0.077 Uiso 1 1 calc R U . . .
C16 C -0.0100(2) 0.65959(10) 0.10807(9) 0.0793(5) Uani 1 1 d . U . . .
H16 H -0.067001 0.703880 0.115439 0.095 Uiso 1 1 calc R U . . .
C17 C 0.0085(2) 0.64100(11) 0.05023(9) 0.0798(5) Uani 1 1 d . U . . .
H17 H -0.036803 0.672359 0.018436 0.096 Uiso 1 1 calc R U . . .
C18 C 0.0943(2) 0.57592(10) 0.03976(8) 0.0728(4) Uani 1 1 d . U . . .
H18 H 0.109510 0.564180 0.000887 0.087 Uiso 1 1 calc R U . . .
C19 C 0.15829(19) 0.52763(9) 0.08665(7) 0.0627(4) Uani 1 1 d . U . . .
H19 H 0.214572 0.483191 0.079036 0.075 Uiso 1 1 calc R U . . .
C20 C 0.1210(2) 0.41378(10) 0.53721(8) 0.0690(4) Uani 1 1 d . U . . .
C21 C 0.0439(2) 0.36950(10) 0.57931(7) 0.0689(4) Uani 1 1 d . U . . .
H21A H 0.125363 0.349381 0.610551 0.083 Uiso 1 1 calc R U . . .
H21B H -0.009690 0.325100 0.558416 0.083 Uiso 1 1 calc R U . . .
C22 C -0.07614(18) 0.41497(10) 0.60859(7) 0.0636(4) Uani 1 1 d . U . . .
H22A H -0.122241 0.380010 0.634914 0.076 Uiso 1 1 calc R U . . .
H22B H -0.161377 0.431989 0.577522 0.076 Uiso 1 1 calc R U . . .
C23 C 0.12451(16) 0.45649(8) 0.71350(6) 0.0501(3) Uani 1 1 d . U . . .
C24 C 0.19899(16) 0.50913(8) 0.75751(6) 0.0507(3) Uani 1 1 d . U . . .
H24 H 0.178952 0.562359 0.753227 0.061 Uiso 1 1 calc R U . . .
C25 C 0.30008(16) 0.48213(8) 0.80618(6) 0.0468(3) Uani 1 1 d . U . . .
C26 C 0.32980(16) 0.39967(8) 0.81040(6) 0.0468(3) Uani 1 1 d . U . . .
C27 C 0.24394(17) 0.35180(8) 0.76536(6) 0.0503(3) Uani 1 1 d . U . . .
C28 C 0.2640(2) 0.27028(9) 0.76972(7) 0.0632(4) Uani 1 1 d . U . . .
H28 H 0.205681 0.238003 0.741209 0.076 Uiso 1 1 calc R U . . .
C29 C 0.3681(2) 0.23833(9) 0.81536(7) 0.0675(4) Uani 1 1 d . U . . .
H29 H 0.378298 0.184334 0.817680 0.081 Uiso 1 1 calc R U . . .
C30 C 0.46061(19) 0.28465(9) 0.85902(7) 0.0596(4) Uani 1 1 d . U . . .
C31 C 0.43962(17) 0.36386(8) 0.85586(6) 0.0532(3) Uani 1 1 d . U . . .
H31 H 0.499665 0.395172 0.884621 0.064 Uiso 1 1 calc R U . . .
C32 C 0.5796(3) 0.24708(11) 0.90707(9) 0.0836(5) Uani 1 1 d . U . . .
H32A H 0.634476 0.286770 0.932350 0.125 Uiso 1 1 calc R U . . .
H32B H 0.654965 0.217612 0.888793 0.125 Uiso 1 1 calc R U . . .
H32C H 0.525129 0.212910 0.930706 0.125 Uiso 1 1 calc R U . . .
C33 C 0.37468(16) 0.53801(7) 0.85280(6) 0.0482(3) Uani 1 1 d . U . . .
C34 C 0.45626(17) 0.60246(8) 0.83629(7) 0.0551(3) Uani 1 1 d . U . . .
H34 H 0.462353 0.610663 0.796030 0.066 Uiso 1 1 calc R U . . .
C35 C 0.5290(2) 0.65495(9) 0.87889(8) 0.0675(4) Uani 1 1 d . U . . .
H35 H 0.584742 0.697476 0.867260 0.081 Uiso 1 1 calc R U . . .
C36 C 0.5181(2) 0.64372(10) 0.93845(8) 0.0717(5) Uani 1 1 d . U . . .
H36 H 0.567800 0.678283 0.967245 0.086 Uiso 1 1 calc R U . . .
C37 C 0.4337(2) 0.58133(10) 0.95531(7) 0.0703(4) Uani 1 1 d . U . . .
H37 H 0.424050 0.574716 0.995438 0.084 Uiso 1 1 calc R U . . .
C38 C 0.36281(19) 0.52819(9) 0.91296(7) 0.0602(4) Uani 1 1 d . U . . .
H38 H 0.307127 0.485818 0.924893 0.072 Uiso 1 1 calc R U . . .
N2 N 0.34702(15) 0.40197(8) 0.29435(6) 0.0602(3) Uani 1 1 d . U . . .
N4 N 0.14145(14) 0.38063(7) 0.71706(5) 0.0534(3) Uani 1 1 d . U . . .
N5 N 0.1840(2) 0.44679(12) 0.50450(8) 0.0997(5) Uani 1 1 d . U . . .
S1 S 0.49355(6) 0.52463(3) 0.35187(2) 0.08229(18) Uani 1 1 d . U . . .
S2 S 0.00197(4) 0.49900(2) 0.65127(2) 0.05770(15) Uani 1 1 d . 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
C1A N1A 1.166(12) . ?
C1A C2A 1.459(7) . ?
C2A C3A 1.518(6) . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C3A S1 1.802(4) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C3B C2B 1.493(11) . ?
C3B S1 1.900(8) . ?
C3B H3B1 0.9700 . ?
C3B H3B2 0.9700 . ?
C1B N1B 1.00(2) . ?
C1B C2B 1.422(14) . ?
C2B H2B1 0.9700 . ?
C2B H2B2 0.9700 . ?
C4 N2 1.309(2) . ?
C4 C5 1.413(2) . ?
C4 S1 1.7660(16) . ?
C5 C6 1.361(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.4329(19) . ?
C6 C14 1.4868(19) . ?
C7 C12 1.408(2) . ?
C7 C8 1.414(2) . ?
C8 N2 1.3740(19) . ?
C8 C9 1.410(2) . ?
C9 C10 1.360(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.399(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(2) . ?
C11 C13 1.502(2) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.382(2) . ?
C14 C19 1.389(2) . ?
C15 C16 1.383(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 N5 1.131(2) . ?
C20 C21 1.452(3) . ?
C21 C22 1.518(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 S2 1.7999(16) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 N4 1.3088(18) . ?
C23 C24 1.4149(19) . ?
C23 S2 1.7681(14) . ?
C24 C25 1.3642(19) . ?
C24 H24 0.9300 . ?
C25 C26 1.4358(18) . ?
C25 C33 1.4882(18) . ?
C26 C31 1.4135(19) . ?
C26 C27 1.4156(18) . ?
C27 N4 1.3753(17) . ?
C27 C28 1.409(2) . ?
C28 C29 1.362(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.405(2) . ?
C29 H29 0.9300 . ?
C30 C31 1.369(2) . ?
C30 C32 1.505(2) . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.387(2) . ?
C33 C38 1.389(2) . ?
C34 C35 1.388(2) . ?
C34 H34 0.9300 . ?
C35 C36 1.377(2) . ?
C35 H35 0.9300 . ?
C36 C37 1.375(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.387(2) . ?
C37 H37 0.9300 . ?
C38 H38 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
N1A C1A C2A 178.2(8) . . ?
C1A C2A C3A 111.6(4) . . ?
C1A C2A H2A1 109.3 . . ?
C3A C2A H2A1 109.3 . . ?
C1A C2A H2A2 109.3 . . ?
C3A C2A H2A2 109.3 . . ?
H2A1 C2A H2A2 108.0 . . ?
C2A C3A S1 108.5(3) . . ?
C2A C3A H3A1 110.0 . . ?
S1 C3A H3A1 110.0 . . ?
C2A C3A H3A2 110.0 . . ?
S1 C3A H3A2 110.0 . . ?
H3A1 C3A H3A2 108.4 . . ?
C2B C3B S1 109.3(6) . . ?
C2B C3B H3B1 109.8 . . ?
S1 C3B H3B1 109.8 . . ?
C2B C3B H3B2 109.8 . . ?
S1 C3B H3B2 109.8 . . ?
H3B1 C3B H3B2 108.3 . . ?
N1B C1B C2B 176.7(18) . . ?
C1B C2B C3B 111.6(8) . . ?
C1B C2B H2B1 109.3 . . ?
C3B C2B H2B1 109.3 . . ?
C1B C2B H2B2 109.3 . . ?
C3B C2B H2B2 109.3 . . ?
H2B1 C2B H2B2 108.0 . . ?
N2 C4 C5 124.18(14) . . ?
N2 C4 S1 120.00(12) . . ?
C5 C4 S1 115.81(12) . . ?
C6 C5 C4 120.16(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 117.96(13) . . ?
C5 C6 C14 120.06(13) . . ?
C7 C6 C14 121.98(13) . . ?
C12 C7 C8 118.84(13) . . ?
C12 C7 C6 123.83(13) . . ?
C8 C7 C6 117.33(13) . . ?
N2 C8 C9 118.01(14) . . ?
N2 C8 C7 123.47(13) . . ?
C9 C8 C7 118.52(14) . . ?
C10 C9 C8 120.19(15) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 122.41(15) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C12 C11 C10 117.81(15) . . ?
C12 C11 C13 121.60(16) . . ?
C10 C11 C13 120.59(15) . . ?
C11 C12 C7 122.08(15) . . ?
C11 C12 H12 119.0 . . ?
C7 C12 H12 119.0 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.72(14) . . ?
C15 C14 C6 119.70(14) . . ?
C19 C14 C6 121.57(13) . . ?
C14 C15 C16 120.89(16) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 119.98(16) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 119.67(16) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.54(17) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 120.16(15) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
N5 C20 C21 178.2(2) . . ?
C20 C21 C22 115.02(14) . . ?
C20 C21 H21A 108.5 . . ?
C22 C21 H21A 108.5 . . ?
C20 C21 H21B 108.5 . . ?
C22 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 S2 115.30(11) . . ?
C21 C22 H22A 108.4 . . ?
S2 C22 H22A 108.4 . . ?
C21 C22 H22B 108.4 . . ?
S2 C22 H22B 108.4 . . ?
H22A C22 H22B 107.5 . . ?
N4 C23 C24 123.88(13) . . ?
N4 C23 S2 120.20(11) . . ?
C24 C23 S2 115.92(10) . . ?
C25 C24 C23 120.27(13) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 117.96(12) . . ?
C24 C25 C33 119.66(12) . . ?
C26 C25 C33 122.38(12) . . ?
C31 C26 C27 118.43(12) . . ?
C31 C26 C25 124.35(12) . . ?
C27 C26 C25 117.22(12) . . ?
N4 C27 C28 117.78(13) . . ?
N4 C27 C26 123.44(12) . . ?
C28 C27 C26 118.78(13) . . ?
C29 C28 C27 120.55(14) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 121.87(14) . . ?
C28 C29 H29 119.1 . . ?
C30 C29 H29 119.1 . . ?
C31 C30 C29 118.01(14) . . ?
C31 C30 C32 121.90(15) . . ?
C29 C30 C32 120.09(14) . . ?
C30 C31 C26 122.25(13) . . ?
C30 C31 H31 118.9 . . ?
C26 C31 H31 118.9 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C38 118.50(13) . . ?
C34 C33 C25 119.83(12) . . ?
C38 C33 C25 121.66(13) . . ?
C33 C34 C35 121.09(14) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C36 C35 C34 119.65(15) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C37 C36 C35 119.94(15) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C38 120.53(16) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 H37 119.7 . . ?
C37 C38 C33 120.25(15) . . ?
C37 C38 H38 119.9 . . ?
C33 C38 H38 119.9 . . ?
C4 N2 C8 116.74(13) . . ?
C23 N4 C27 117.07(12) . . ?
C4 S1 C3A 102.73(11) . . ?
C4 S1 C3B 99.20(17) . . ?
C23 S2 C22 102.52(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
C1A C2A C3A S1 169.7(2) . . . . ?
S1 C3B C2B C1B -166.0(5) . . . . ?
N2 C4 C5 C6 2.7(2) . . . . ?
S1 C4 C5 C6 -177.74(11) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C4 C5 C6 C14 -179.08(13) . . . . ?
C5 C6 C7 C12 176.26(13) . . . . ?
C14 C6 C7 C12 -4.0(2) . . . . ?
C5 C6 C7 C8 -3.5(2) . . . . ?
C14 C6 C7 C8 176.22(13) . . . . ?
C12 C7 C8 N2 -176.17(13) . . . . ?
C6 C7 C8 N2 3.6(2) . . . . ?
C12 C7 C8 C9 4.2(2) . . . . ?
C6 C7 C8 C9 -176.06(14) . . . . ?
N2 C8 C9 C10 178.18(16) . . . . ?
C7 C8 C9 C10 -2.1(3) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 2.5(3) . . . . ?
C9 C10 C11 C13 -177.00(19) . . . . ?
C10 C11 C12 C7 -0.3(3) . . . . ?
C13 C11 C12 C7 179.18(16) . . . . ?
C8 C7 C12 C11 -3.0(2) . . . . ?
C6 C7 C12 C11 177.22(15) . . . . ?
C5 C6 C14 C15 -55.32(19) . . . . ?
C7 C6 C14 C15 124.96(16) . . . . ?
C5 C6 C14 C19 123.92(16) . . . . ?
C7 C6 C14 C19 -55.80(19) . . . . ?
C19 C14 C15 C16 2.1(2) . . . . ?
C6 C14 C15 C16 -178.64(15) . . . . ?
C14 C15 C16 C17 -1.4(3) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C16 C17 C18 C19 1.9(3) . . . . ?
C17 C18 C19 C14 -1.1(3) . . . . ?
C15 C14 C19 C18 -0.9(2) . . . . ?
C6 C14 C19 C18 179.90(14) . . . . ?
C20 C21 C22 S2 -59.60(17) . . . . ?
N4 C23 C24 C25 2.6(2) . . . . ?
S2 C23 C24 C25 -177.77(10) . . . . ?
C23 C24 C25 C26 1.1(2) . . . . ?
C23 C24 C25 C33 -178.62(12) . . . . ?
C24 C25 C26 C31 175.45(13) . . . . ?
C33 C25 C26 C31 -4.8(2) . . . . ?
C24 C25 C26 C27 -3.81(19) . . . . ?
C33 C25 C26 C27 175.92(12) . . . . ?
C31 C26 C27 N4 -175.92(12) . . . . ?
C25 C26 C27 N4 3.4(2) . . . . ?
C31 C26 C27 C28 3.9(2) . . . . ?
C25 C26 C27 C28 -176.82(13) . . . . ?
N4 C27 C28 C29 177.65(14) . . . . ?
C26 C27 C28 C29 -2.2(2) . . . . ?
C27 C28 C29 C30 -0.9(3) . . . . ?
C28 C29 C30 C31 2.2(3) . . . . ?
C28 C29 C30 C32 -177.24(17) . . . . ?
C29 C30 C31 C26 -0.4(2) . . . . ?
C32 C30 C31 C26 179.08(15) . . . . ?
C27 C26 C31 C30 -2.7(2) . . . . ?
C25 C26 C31 C30 178.08(14) . . . . ?
C24 C25 C33 C34 -52.90(18) . . . . ?
C26 C25 C33 C34 127.37(14) . . . . ?
C24 C25 C33 C38 126.03(15) . . . . ?
C26 C25 C33 C38 -53.70(19) . . . . ?
C38 C33 C34 C35 2.0(2) . . . . ?
C25 C33 C34 C35 -179.06(13) . . . . ?
C33 C34 C35 C36 -1.0(2) . . . . ?
C34 C35 C36 C37 -0.9(3) . . . . ?
C35 C36 C37 C38 1.8(3) . . . . ?
C36 C37 C38 C33 -0.8(2) . . . . ?
C34 C33 C38 C37 -1.1(2) . . . . ?
C25 C33 C38 C37 -179.99(14) . . . . ?
C5 C4 N2 C8 -2.7(2) . . . . ?
S1 C4 N2 C8 177.74(11) . . . . ?
C9 C8 N2 C4 179.15(15) . . . . ?
C7 C8 N2 C4 -0.5(2) . . . . ?
C24 C23 N4 C27 -3.1(2) . . . . ?
S2 C23 N4 C27 177.24(10) . . . . ?
C28 C27 N4 C23 -179.75(13) . . . . ?
C26 C27 N4 C23 0.1(2) . . . . ?
N2 C4 S1 C3A -14.72(18) . . . . ?
C5 C4 S1 C3A 165.71(16) . . . . ?
N2 C4 S1 C3B 17.5(2) . . . . ?
C5 C4 S1 C3B -162.1(2) . . . . ?
C2A C3A S1 C4 83.0(2) . . . . ?
C2B C3B S1 C4 -90.1(4) . . . . ?
N4 C23 S2 C22 2.28(13) . . . . ?
C24 C23 S2 C22 -177.40(11) . . . . ?
C21 C22 S2 C23 -69.44(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
C21 H21B N1A 0.97 2.56 3.312(13) 134.8 1_455
C21 H21A N4 0.97 2.45 3.0957(19) 124.0 .
C3B H3B2 N5 0.97 2.68 3.418(6) 133.1 3_666
C2A H2A2 S2 0.97 2.94 3.889(4) 167.4 3_666
C2A H2A1 N2 0.97 2.61 3.202(4) 119.9 .
C21 H21B N1A 0.97 2.56 3.312(13) 134.8 1_455
C21 H21A N4 0.97 2.45 3.0957(19) 124.0 .
C3B H3B2 N5 0.97 2.68 3.418(6) 133.1 3_666
C2A H2A2 S2 0.97 2.94 3.889(4) 167.4 3_666
C2A H2A1 N2 0.97 2.61 3.202(4) 119.9 .
C21 H21B N1A 0.97 2.56 3.312(13) 134.8 1_455
C21 H21A N4 0.97 2.45 3.0957(19) 124.0 .
C21 H21B N1A 0.97 2.56 3.312(13) 134.8 1_455
C21 H21A N4 0.97 2.45 3.0957(19) 124.0 .
C21 H21A N4 0.97 2.45 3.0957(19) 124.0 .
C21 H21B N1A 0.97 2.56 3.312(13) 134.8 1_455
C2A H2A1 N2 0.97 2.61 3.202(4) 119.9 .
C2A H2A2 S2 0.97 2.94 3.889(4) 167.4 3_666
C3B H3B2 N5 0.97 2.68 3.418(6) 133.1 3_666
C21 H21A N4 0.97 2.45 3.0957(19) 124.0 .
C21 H21B N1A 0.97 2.56 3.312(13) 134.8 1_455
C2A H2A1 N2 0.97 2.61 3.202(4) 119.9 .
C2A H2A2 S2 0.97 2.94 3.889(4) 167.4 3_666
C3B H3B2 N5 0.97 2.68 3.418(6) 133.1 3_666
C21 H21A N4 0.97 2.45 3.0957(19) 124.0 .
C21 H21B N1A 0.97 2.56 3.312(13) 134.8 1_455

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.031

