# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_hb238_rt
_database_code_depnum_ccdc_archive 'CCDC 2073437'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universitaet zu Koeln
Germany
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-06-23 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         'C23 H30 N4 S2'
_chemical_formula_sum            'C23 H30 N4 S2'
_chemical_formula_weight         426.63

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'
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           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                   13.0876(10)
_cell_length_b                   19.2985(12)
_cell_length_c                   9.8422(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.654(3)
_cell_angle_gamma                90
_cell_volume                     2434.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    8199
_cell_measurement_theta_min      2.111
_cell_measurement_theta_max      24.995

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.984
_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      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  Nonius
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8199
_diffrn_reflns_av_unetI/netI     0.0930
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.111
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4247
_reflns_number_gt                1859
_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       'Nonius COLLECT'
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2017)'

_refine_special_details          'disorder in alkylgroup is not refined!'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0898P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4247
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1490
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1731
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_restrained_S_all      0.900
_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
S1 S 0.21521(8) 0.23470(4) -0.01144(10) 0.0832(4) Uani 1 1 d . . . . .
S2 S 0.29928(8) 0.38595(5) 0.05350(10) 0.0836(4) Uani 1 1 d . . . . .
N1 N 0.1088(3) 0.12278(15) -0.1214(4) 0.1010(11) Uani 1 1 d . . . . .
N2 N 0.4517(2) 0.45448(15) 0.2050(3) 0.0788(8) Uani 1 1 d . . . . .
N3 N 0.4536(3) 0.63325(17) 0.0934(4) 0.1157(12) Uani 1 1 d . . . . .
N4 N 0.1912(4) 0.52937(18) -0.1787(5) 0.1365(16) Uani 1 1 d . . . . .
C1 C 0.1795(3) 0.14796(18) -0.0169(4) 0.0807(11) Uani 1 1 d . . . . .
C2 C 0.0789(4) 0.0489(2) -0.1273(5) 0.1100(15) Uani 1 1 d . . . . .
H2A H 0.006273 0.044323 -0.173067 0.132 Uiso 1 1 calc R U . . .
H2B H 0.086508 0.030850 -0.033863 0.132 Uiso 1 1 calc R U . . .
C3 C 0.1480(4) 0.0067(2) -0.2073(5) 0.1363(18) Uani 1 1 d . . . . .
H3A H 0.141663 0.026482 -0.299230 0.164 Uiso 1 1 calc R U . . .
H3B H 0.220215 0.011480 -0.159962 0.164 Uiso 1 1 calc R U . . .
C4 C 0.1217(5) -0.0691(3) -0.2217(7) 0.183(3) Uani 1 1 d . . . . .
H4A H 0.178208 -0.093546 -0.251252 0.220 Uiso 1 1 calc R U . . .
H4B H 0.115279 -0.087372 -0.132033 0.220 Uiso 1 1 calc R U . . .
C5 C 0.0246(6) -0.0817(3) -0.3218(9) 0.258(4) Uani 1 1 d . . . . .
H5A H -0.033498 -0.076709 -0.276580 0.386 Uiso 1 1 calc R U . . .
H5B H 0.025253 -0.127846 -0.358073 0.386 Uiso 1 1 calc R U . . .
H5C H 0.018272 -0.048889 -0.396274 0.386 Uiso 1 1 calc R U . . .
C6 C 0.0642(4) 0.1649(2) -0.2460(5) 0.1201(16) Uani 1 1 d . . . . .
H6A H 0.110120 0.203509 -0.253540 0.144 Uiso 1 1 calc R U . . .
H6B H 0.058422 0.136633 -0.328758 0.144 Uiso 1 1 calc R U . . .
C7 C -0.0388(5) 0.1908(3) -0.2350(6) 0.158(2) Uani 1 1 d . . . . .
H7A H -0.032886 0.219783 -0.153323 0.190 Uiso 1 1 calc R U . . .
H7B H -0.084391 0.152177 -0.225736 0.190 Uiso 1 1 calc R U . . .
C8 C -0.0848(7) 0.2326(4) -0.3643(8) 0.228(4) Uani 1 1 d . . . . .
H8A H -0.072435 0.281178 -0.341621 0.273 Uiso 1 1 calc R U . . .
H8B H -0.045217 0.221361 -0.434724 0.273 Uiso 1 1 calc R U . . .
C9 C -0.1736(8) 0.2265(7) -0.4150(13) 0.413(11) Uani 1 1 d . . . . .
H9A H -0.187447 0.179394 -0.444597 0.620 Uiso 1 1 calc R U . . .
H9B H -0.190977 0.256807 -0.493593 0.620 Uiso 1 1 calc R U . . .
H9C H -0.215109 0.238212 -0.348242 0.620 Uiso 1 1 calc R U . . .
C10 C 0.2342(3) 0.11220(19) 0.0970(4) 0.0923(12) Uani 1 1 d . . . . .
H10 H 0.224604 0.065419 0.113298 0.111 Uiso 1 1 calc R U . . .
C11 C 0.3038(3) 0.15351(18) 0.1823(4) 0.0886(12) Uani 1 1 d . . . . .
H11 H 0.347198 0.136485 0.261927 0.106 Uiso 1 1 calc R U . . .
C12 C 0.3058(3) 0.22255(17) 0.1431(3) 0.0739(10) Uani 1 1 d . . . . .
C13 C 0.3736(3) 0.27202(18) 0.2122(4) 0.0780(10) Uani 1 1 d . . . . .
H13 H 0.420622 0.255422 0.289004 0.094 Uiso 1 1 calc R U . . .
C14 C 0.3835(3) 0.34224(18) 0.1862(3) 0.0726(10) Uani 1 1 d . . . . .
C15 C 0.3708(3) 0.46170(17) 0.0982(4) 0.0759(10) Uani 1 1 d . . . . .
C16 C 0.4594(3) 0.3900(2) 0.2544(4) 0.0789(10) Uani 1 1 d . . . . .
C17 C 0.5511(4) 0.3729(2) 0.3709(4) 0.0977(13) Uani 1 1 d . . . . .
C18 C 0.5159(4) 0.3430(3) 0.4969(4) 0.1434(19) Uani 1 1 d . . . . .
H18A H 0.467188 0.374179 0.525830 0.215 Uiso 1 1 calc R U . . .
H18B H 0.575284 0.337090 0.571097 0.215 Uiso 1 1 calc R U . . .
H18C H 0.482947 0.299016 0.473245 0.215 Uiso 1 1 calc R U . . .
C19 C 0.6155(4) 0.4383(2) 0.4153(5) 0.151(2) Uani 1 1 d . . . . .
H19A H 0.631831 0.460516 0.335032 0.226 Uiso 1 1 calc R U . . .
H19B H 0.679016 0.425960 0.478102 0.226 Uiso 1 1 calc R U . . .
H19C H 0.576116 0.469552 0.460749 0.226 Uiso 1 1 calc R U . . .
C20 C 0.6230(4) 0.3200(3) 0.3145(5) 0.1389(19) Uani 1 1 d . . . . .
H20A H 0.587600 0.276316 0.297034 0.208 Uiso 1 1 calc R U . . .
H20B H 0.686440 0.313782 0.381929 0.208 Uiso 1 1 calc R U . . .
H20C H 0.639080 0.337307 0.229786 0.208 Uiso 1 1 calc R U . . .
C21 C 0.3466(3) 0.52372(19) 0.0274(4) 0.0831(11) Uani 1 1 d . . . . .
C22 C 0.4066(3) 0.5836(2) 0.0651(4) 0.0895(12) Uani 1 1 d . . . . .
C23 C 0.2619(4) 0.52740(19) -0.0857(6) 0.1010(14) 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 C1 1.736(4) . ?
S1 C12 1.745(4) . ?
S2 C15 1.744(3) . ?
S2 C14 1.746(4) . ?
N1 C1 1.329(4) . ?
N1 C2 1.476(4) . ?
N1 C6 1.488(5) . ?
N2 C16 1.333(4) . ?
N2 C15 1.341(5) . ?
N3 C22 1.142(4) . ?
N4 C23 1.163(5) . ?
C1 C10 1.386(5) . ?
C2 C3 1.546(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.503(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.463(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.462(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.525(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.175(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.364(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(4) . ?
C13 C14 1.390(4) . ?
C13 H13 0.9300 . ?
C14 C16 1.421(5) . ?
C15 C21 1.389(5) . ?
C16 C17 1.519(5) . ?
C17 C18 1.521(5) . ?
C17 C19 1.532(5) . ?
C17 C20 1.565(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.405(5) . ?
C21 C23 1.405(6) . ?

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
C1 S1 C12 91.64(18) . . ?
C15 S2 C14 89.49(18) . . ?
C1 N1 C2 121.4(3) . . ?
C1 N1 C6 122.3(3) . . ?
C2 N1 C6 115.9(3) . . ?
C16 N2 C15 111.9(3) . . ?
N1 C1 C10 127.5(3) . . ?
N1 C1 S1 121.2(3) . . ?
C10 C1 S1 111.3(3) . . ?
N1 C2 C3 110.6(4) . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 114.5(5) . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C3 112.2(5) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N1 109.8(5) . . ?
C7 C6 H6A 109.7 . . ?
N1 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
N1 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C6 C7 C8 109.5(6) . . ?
C6 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 119.4(10) . . ?
C9 C8 H8A 107.5 . . ?
C7 C8 H8A 107.5 . . ?
C9 C8 H8B 107.5 . . ?
C7 C8 H8B 107.5 . . ?
H8A C8 H8B 107.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C1 112.2(3) . . ?
C11 C10 H10 123.9 . . ?
C1 C10 H10 123.9 . . ?
C10 C11 C12 115.9(4) . . ?
C10 C11 H11 122.0 . . ?
C12 C11 H11 122.0 . . ?
C13 C12 C11 124.8(4) . . ?
C13 C12 S1 126.2(3) . . ?
C11 C12 S1 108.9(3) . . ?
C12 C13 C14 131.0(4) . . ?
C12 C13 H13 114.5 . . ?
C14 C13 H13 114.5 . . ?
C13 C14 C16 128.8(4) . . ?
C13 C14 S2 122.7(3) . . ?
C16 C14 S2 108.4(3) . . ?
N2 C15 C21 123.2(3) . . ?
N2 C15 S2 114.2(3) . . ?
C21 C15 S2 122.7(3) . . ?
N2 C16 C14 116.0(3) . . ?
N2 C16 C17 117.9(3) . . ?
C14 C16 C17 126.0(4) . . ?
C16 C17 C18 112.0(4) . . ?
C16 C17 C19 110.0(3) . . ?
C18 C17 C19 108.7(4) . . ?
C16 C17 C20 108.2(3) . . ?
C18 C17 C20 110.2(4) . . ?
C19 C17 C20 107.7(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C21 C22 121.2(4) . . ?
C15 C21 C23 120.3(3) . . ?
C22 C21 C23 118.5(3) . . ?
N3 C22 C21 178.3(5) . . ?
N4 C23 C21 178.9(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
C2 N1 C1 C10 0.1(7) . . . . ?
C6 N1 C1 C10 -172.9(4) . . . . ?
C2 N1 C1 S1 179.4(3) . . . . ?
C6 N1 C1 S1 6.5(6) . . . . ?
C12 S1 C1 N1 -178.4(3) . . . . ?
C12 S1 C1 C10 1.0(3) . . . . ?
C1 N1 C2 C3 -91.1(5) . . . . ?
C6 N1 C2 C3 82.2(5) . . . . ?
N1 C2 C3 C4 -178.7(4) . . . . ?
C2 C3 C4 C5 73.2(7) . . . . ?
C1 N1 C6 C7 -100.5(5) . . . . ?
C2 N1 C6 C7 86.2(5) . . . . ?
N1 C6 C7 C8 -178.9(4) . . . . ?
C6 C7 C8 C9 138.9(13) . . . . ?
N1 C1 C10 C11 177.8(4) . . . . ?
S1 C1 C10 C11 -1.6(5) . . . . ?
C1 C10 C11 C12 1.5(5) . . . . ?
C10 C11 C12 C13 -177.1(4) . . . . ?
C10 C11 C12 S1 -0.7(4) . . . . ?
C1 S1 C12 C13 176.1(3) . . . . ?
C1 S1 C12 C11 -0.2(3) . . . . ?
C11 C12 C13 C14 -179.0(4) . . . . ?
S1 C12 C13 C14 5.2(6) . . . . ?
C12 C13 C14 C16 -175.0(4) . . . . ?
C12 C13 C14 S2 3.6(6) . . . . ?
C15 S2 C14 C13 -178.5(3) . . . . ?
C15 S2 C14 C16 0.3(3) . . . . ?
C16 N2 C15 C21 -179.2(3) . . . . ?
C16 N2 C15 S2 -0.2(4) . . . . ?
C14 S2 C15 N2 -0.1(3) . . . . ?
C14 S2 C15 C21 178.9(3) . . . . ?
C15 N2 C16 C14 0.5(5) . . . . ?
C15 N2 C16 C17 176.8(3) . . . . ?
C13 C14 C16 N2 178.2(3) . . . . ?
S2 C14 C16 N2 -0.6(4) . . . . ?
C13 C14 C16 C17 2.3(6) . . . . ?
S2 C14 C16 C17 -176.5(3) . . . . ?
N2 C16 C17 C18 124.4(4) . . . . ?
C14 C16 C17 C18 -59.7(5) . . . . ?
N2 C16 C17 C19 3.5(5) . . . . ?
C14 C16 C17 C19 179.4(4) . . . . ?
N2 C16 C17 C20 -113.9(4) . . . . ?
C14 C16 C17 C20 61.9(5) . . . . ?
N2 C15 C21 C22 -0.4(6) . . . . ?
S2 C15 C21 C22 -179.3(3) . . . . ?
N2 C15 C21 C23 178.7(4) . . . . ?
S2 C15 C21 C23 -0.2(6) . . . . ?

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_hb238_tt
_database_code_depnum_ccdc_archive 'CCDC 2073438'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universitaet zu Koeln
Germany
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-06-23 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         'C23 H30 N4 S2'

_chemical_formula_sum            'C23 H30 N4 S2'
_chemical_formula_weight         426.63

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'
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           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                   13.9396(17)
_cell_length_b                   18.847(2)
_cell_length_c                   9.0814(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.608(6)
_cell_angle_gamma                90
_cell_volume                     2297.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11688
_cell_measurement_theta_min      2.161
_cell_measurement_theta_max      27.482

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_crystal_preparation       
;
slow cooling from 293 to 240k with 5 k/h,  from 240 k to 100k with  20 k/h
;
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.988
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  Nonius
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11688
_diffrn_reflns_av_unetI/netI     0.1142
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.161
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5249
_reflns_number_gt                3286
_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       'Nonius COLLECT'
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2017)'


_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)+13.0738P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5249
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1645
_refine_ls_R_factor_gt           0.1050
_refine_ls_wR_factor_ref         0.2425
_refine_ls_wR_factor_gt          0.2266
_refine_ls_goodness_of_fit_ref   1.280
_refine_ls_restrained_S_all      1.280
_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 0.19013(11) 0.24282(8) 0.02401(17) 0.0254(4) Uani 1 1 d . . . . .
S2 S 0.30066(12) 0.09422(9) 0.06185(19) 0.0316(4) Uani 1 1 d . . . . .
N1 N 0.0721(4) 0.3547(3) -0.0853(6) 0.0294(12) Uani 1 1 d . . . . .
N2 N 0.4622(4) 0.0303(3) 0.2164(6) 0.0264(12) Uani 1 1 d . . . . .
N3 N 0.1981(4) -0.0517(3) -0.2085(7) 0.0380(14) Uani 1 1 d . . . . .
N4 N 0.4720(4) -0.1512(3) 0.0585(6) 0.0310(13) Uani 1 1 d . . . . .
C1 C 0.1565(4) 0.3316(3) 0.0117(7) 0.0266(14) Uani 1 1 d . . . . .
C2 C 0.0008(4) 0.3069(4) -0.1820(7) 0.0294(15) Uani 1 1 d . . . . .
H2A H 0.037560 0.268723 -0.218430 0.035 Uiso 1 1 calc R U . . .
H2B H -0.037994 0.333330 -0.272649 0.035 Uiso 1 1 calc R U . . .
C3 C -0.0709(4) 0.2733(3) -0.1027(7) 0.0274(14) Uani 1 1 d . . . . .
H3A H -0.032554 0.243394 -0.017492 0.033 Uiso 1 1 calc R U . . .
H3B H -0.103288 0.311400 -0.058274 0.033 Uiso 1 1 calc R U . . .
C4 C -0.1506(5) 0.2284(4) -0.2072(7) 0.0332(16) Uani 1 1 d . . . . .
H4A H -0.198477 0.260023 -0.277749 0.040 Uiso 1 1 calc R U . . .
H4B H -0.119263 0.197836 -0.269848 0.040 Uiso 1 1 calc R U . . .
C5 C -0.2065(5) 0.1825(4) -0.1244(7) 0.0329(15) Uani 1 1 d . . . . .
H5A H -0.159577 0.151986 -0.051860 0.049 Uiso 1 1 calc R U . . .
H5B H -0.254111 0.152897 -0.198226 0.049 Uiso 1 1 calc R U . . .
H5C H -0.242519 0.212405 -0.068906 0.049 Uiso 1 1 calc R U . . .
C10 C 0.2280(5) 0.3730(4) 0.1147(8) 0.0371(17) Uani 1 1 d . . . . .
H10 H 0.222356 0.422900 0.125220 0.045 Uiso 1 1 calc R U . . .
C11 C 0.3068(5) 0.3338(4) 0.1983(7) 0.0314(15) Uani 1 1 d . . . . .
H11 H 0.361075 0.354540 0.272137 0.038 Uiso 1 1 calc R U . . .
C12 C 0.3014(4) 0.2613(3) 0.1672(7) 0.0249(13) Uani 1 1 d . . . . .
C13 C 0.3743(4) 0.2126(3) 0.2356(6) 0.0245(13) Uani 1 1 d . . . . .
H13 H 0.426129 0.231531 0.316323 0.029 Uiso 1 1 calc R U . . .
C14 C 0.3851(4) 0.1408(3) 0.2071(7) 0.0267(14) Uani 1 1 d . . . . .
C15 C 0.3796(4) 0.0207(3) 0.0992(7) 0.0267(14) Uani 1 1 d . . . . .
C16 C 0.4667(4) 0.0948(3) 0.2765(7) 0.0254(13) Uani 1 1 d . . . . .
C17 C 0.5557(4) 0.1142(3) 0.4086(7) 0.0269(14) Uani 1 1 d . . . . .
C18 C 0.6192(4) 0.1722(3) 0.3600(7) 0.0293(15) Uani 1 1 d . . . . .
H18A H 0.640526 0.155785 0.271462 0.044 Uiso 1 1 calc R U . . .
H18B H 0.677925 0.182259 0.444952 0.044 Uiso 1 1 calc R U . . .
H18C H 0.579458 0.215552 0.332947 0.044 Uiso 1 1 calc R U . . .
C19 C 0.5210(5) 0.1412(4) 0.5465(7) 0.0327(15) Uani 1 1 d . . . . .
H19A H 0.476725 0.182032 0.515169 0.049 Uiso 1 1 calc R U . . .
H19B H 0.579114 0.155416 0.628804 0.049 Uiso 1 1 calc R U . . .
H19C H 0.485204 0.103227 0.583080 0.049 Uiso 1 1 calc R U . . .
C20 C 0.6225(5) 0.0487(4) 0.4600(8) 0.0373(17) Uani 1 1 d . . . . .
H20A H 0.583186 0.010487 0.488190 0.056 Uiso 1 1 calc R U . . .
H20B H 0.677687 0.061208 0.548565 0.056 Uiso 1 1 calc R U . . .
H20C H 0.649148 0.032810 0.376153 0.056 Uiso 1 1 calc R U . . .
C21 C 0.3574(4) -0.0419(3) 0.0140(7) 0.0269(14) Uani 1 1 d . . . . .
C22 C 0.2695(5) -0.0468(3) -0.1099(8) 0.0306(15) Uani 1 1 d . . . . .
C23 C 0.4222(5) -0.1016(4) 0.0401(6) 0.0263(14) Uani 1 1 d . . . . .
C6X C 0.0529(16) 0.4268(11) -0.1413(19) 0.024(4) Uani 0.465(13) 1 d . . P A 1
H6XA H 0.072516 0.459690 -0.053336 0.029 Uiso 0.465(13) 1 calc R U P A 1
H6XB H -0.019608 0.432408 -0.187306 0.029 Uiso 0.465(13) 1 calc R U P A 1
C1X C 0.1063(11) 0.4476(9) -0.257(2) 0.035(4) Uani 0.465(13) 1 d . . P A 1
H1XA H 0.079061 0.419550 -0.351017 0.042 Uiso 0.465(13) 1 calc R U P A 1
H1XB H 0.177507 0.434891 -0.216857 0.042 Uiso 0.465(13) 1 calc R U P A 1
C2X C 0.0990(11) 0.5265(8) -0.299(2) 0.041(5) Uani 0.465(13) 1 d . . P A 1
H2XA H 0.129231 0.554541 -0.205789 0.050 Uiso 0.465(13) 1 calc R U P A 1
H2XB H 0.138409 0.535349 -0.372905 0.050 Uiso 0.465(13) 1 calc R U P A 1
C3X C -0.0076(11) 0.5524(8) -0.3680(18) 0.036(4) Uani 0.465(13) 1 d . . P A 1
H3XA H -0.006051 0.600667 -0.407659 0.054 Uiso 0.465(13) 1 calc R U P A 1
H3XB H -0.043616 0.552546 -0.289024 0.054 Uiso 0.465(13) 1 calc R U P A 1
H3XC H -0.041287 0.520783 -0.451454 0.054 Uiso 0.465(13) 1 calc R U P A 1
C6Y C 0.0530(13) 0.4334(9) -0.0769(17) 0.021(3) Uani 0.535(13) 1 d . . P A 2
H6YA H -0.019366 0.442836 -0.113256 0.025 Uiso 0.535(13) 1 calc R U P A 2
H6YB H 0.076625 0.449599 0.030530 0.025 Uiso 0.535(13) 1 calc R U P A 2
C1Y C 0.1066(10) 0.4734(8) -0.1738(18) 0.034(3) Uani 0.535(13) 1 d . . P A 2
H1YA H 0.081242 0.457921 -0.281486 0.041 Uiso 0.535(13) 1 calc R U P A 2
H1YB H 0.178519 0.462034 -0.139744 0.041 Uiso 0.535(13) 1 calc R U P A 2
C2Y C 0.0927(9) 0.5549(7) -0.1646(16) 0.039(4) Uani 0.535(13) 1 d . . P A 2
H2YA H 0.143949 0.579532 -0.202793 0.046 Uiso 0.535(13) 1 calc R U P A 2
H2YB H 0.101705 0.568896 -0.056713 0.046 Uiso 0.535(13) 1 calc R U P A 2
C3Y C -0.0130(11) 0.5779(8) -0.2615(19) 0.050(4) Uani 0.535(13) 1 d . . P A 2
H3YA H -0.016593 0.574221 -0.370471 0.074 Uiso 0.535(13) 1 calc R U P A 2
H3YB H -0.025418 0.627146 -0.236932 0.074 Uiso 0.535(13) 1 calc R U P A 2
H3YC H -0.063319 0.546955 -0.237849 0.074 Uiso 0.535(13) 1 calc R U P A 2


_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 C1 1.733(6) . ?
S1 C12 1.770(6) . ?
S2 C15 1.745(6) . ?
S2 C14 1.750(6) . ?
N1 C1 1.339(8) . ?
N1 C2 1.449(8) . ?
N1 C6X 1.45(2) . ?
N1 C6Y 1.512(17) . ?
N2 C16 1.327(8) . ?
N2 C15 1.354(7) . ?
N3 C22 1.150(8) . ?
N4 C23 1.150(8) . ?
C1 C10 1.407(9) . ?
C2 C3 1.517(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.512(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.496(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C10 C11 1.371(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(8) . ?
C13 C14 1.393(9) . ?
C13 H13 0.9500 . ?
C14 C16 1.434(8) . ?
C15 C21 1.399(9) . ?
C16 C17 1.520(8) . ?
C17 C20 1.540(9) . ?
C17 C18 1.544(8) . ?
C17 C19 1.546(8) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C23 1.422(9) . ?
C21 C22 1.426(9) . ?
C6X C1X 1.49(2) . ?
C6X H6XA 0.9900 . ?
C6X H6XB 0.9900 . ?
C1X C2X 1.53(2) . ?
C1X H1XA 0.9900 . ?
C1X H1XB 0.9900 . ?
C2X C3X 1.53(2) . ?
C2X H2XA 0.9900 . ?
C2X H2XB 0.9900 . ?
C3X H3XA 0.9800 . ?
C3X H3XB 0.9800 . ?
C3X H3XC 0.9800 . ?
C6Y C1Y 1.50(2) . ?
C6Y H6YA 0.9900 . ?
C6Y H6YB 0.9900 . ?
C1Y C2Y 1.552(19) . ?
C1Y H1YA 0.9900 . ?
C1Y H1YB 0.9900 . ?
C2Y C3Y 1.560(18) . ?
C2Y H2YA 0.9900 . ?
C2Y H2YB 0.9900 . ?
C3Y H3YA 0.9800 . ?
C3Y H3YB 0.9800 . ?
C3Y H3YC 0.9800 . ?

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
C1 S1 C12 91.5(3) . . ?
C15 S2 C14 89.5(3) . . ?
C1 N1 C2 122.2(5) . . ?
C1 N1 C6X 125.6(10) . . ?
C2 N1 C6X 109.8(9) . . ?
C1 N1 C6Y 114.9(8) . . ?
C2 N1 C6Y 122.7(8) . . ?
C16 N2 C15 112.5(5) . . ?
N1 C1 C10 126.6(6) . . ?
N1 C1 S1 122.1(5) . . ?
C10 C1 S1 111.2(5) . . ?
N1 C2 C3 113.8(5) . . ?
N1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
N1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 113.7(5) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 113.8(5) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C10 C1 112.8(6) . . ?
C11 C10 H10 123.6 . . ?
C1 C10 H10 123.6 . . ?
C10 C11 C12 115.2(6) . . ?
C10 C11 H11 122.4 . . ?
C12 C11 H11 122.4 . . ?
C13 C12 C11 124.5(6) . . ?
C13 C12 S1 126.2(5) . . ?
C11 C12 S1 109.3(5) . . ?
C12 C13 C14 131.6(6) . . ?
C12 C13 H13 114.2 . . ?
C14 C13 H13 114.2 . . ?
C13 C14 C16 128.2(6) . . ?
C13 C14 S2 122.8(5) . . ?
C16 C14 S2 108.7(5) . . ?
N2 C15 C21 124.3(6) . . ?
N2 C15 S2 113.9(5) . . ?
C21 C15 S2 121.8(5) . . ?
N2 C16 C14 115.4(5) . . ?
N2 C16 C17 118.8(5) . . ?
C14 C16 C17 125.8(6) . . ?
C16 C17 C20 110.2(5) . . ?
C16 C17 C18 110.7(5) . . ?
C20 C17 C18 108.0(5) . . ?
C16 C17 C19 110.6(5) . . ?
C20 C17 C19 108.2(5) . . ?
C18 C17 C19 109.0(5) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C21 C23 122.6(6) . . ?
C15 C21 C22 120.5(6) . . ?
C23 C21 C22 116.9(6) . . ?
N3 C22 C21 178.8(8) . . ?
N4 C23 C21 177.7(7) . . ?
N1 C6X C1X 114.4(14) . . ?
N1 C6X H6XA 108.7 . . ?
C1X C6X H6XA 108.7 . . ?
N1 C6X H6XB 108.7 . . ?
C1X C6X H6XB 108.7 . . ?
H6XA C6X H6XB 107.6 . . ?
C6X C1X C2X 114.7(15) . . ?
C6X C1X H1XA 108.6 . . ?
C2X C1X H1XA 108.6 . . ?
C6X C1X H1XB 108.6 . . ?
C2X C1X H1XB 108.6 . . ?
H1XA C1X H1XB 107.6 . . ?
C3X C2X C1X 113.9(12) . . ?
C3X C2X H2XA 108.8 . . ?
C1X C2X H2XA 108.8 . . ?
C3X C2X H2XB 108.8 . . ?
C1X C2X H2XB 108.8 . . ?
H2XA C2X H2XB 107.7 . . ?
C2X C3X H3XA 109.5 . . ?
C2X C3X H3XB 109.5 . . ?
H3XA C3X H3XB 109.5 . . ?
C2X C3X H3XC 109.5 . . ?
H3XA C3X H3XC 109.5 . . ?
H3XB C3X H3XC 109.5 . . ?
C1Y C6Y N1 110.0(12) . . ?
C1Y C6Y H6YA 109.7 . . ?
N1 C6Y H6YA 109.7 . . ?
C1Y C6Y H6YB 109.7 . . ?
N1 C6Y H6YB 109.7 . . ?
H6YA C6Y H6YB 108.2 . . ?
C6Y C1Y C2Y 112.1(12) . . ?
C6Y C1Y H1YA 109.2 . . ?
C2Y C1Y H1YA 109.2 . . ?
C6Y C1Y H1YB 109.2 . . ?
C2Y C1Y H1YB 109.2 . . ?
H1YA C1Y H1YB 107.9 . . ?
C1Y C2Y C3Y 111.0(12) . . ?
C1Y C2Y H2YA 109.4 . . ?
C3Y C2Y H2YA 109.4 . . ?
C1Y C2Y H2YB 109.4 . . ?
C3Y C2Y H2YB 109.4 . . ?
H2YA C2Y H2YB 108.0 . . ?
C2Y C3Y H3YA 109.5 . . ?
C2Y C3Y H3YB 109.5 . . ?
H3YA C3Y H3YB 109.5 . . ?
C2Y C3Y H3YC 109.5 . . ?
H3YA C3Y H3YC 109.5 . . ?
H3YB C3Y H3YC 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
C2 N1 C1 C10 -177.0(6) . . . . ?
C6X N1 C1 C10 22.1(13) . . . . ?
C6Y N1 C1 C10 -1.8(11) . . . . ?
C2 N1 C1 S1 2.8(8) . . . . ?
C6X N1 C1 S1 -158.1(9) . . . . ?
C6Y N1 C1 S1 178.0(8) . . . . ?
C12 S1 C1 N1 179.7(5) . . . . ?
C12 S1 C1 C10 -0.4(5) . . . . ?
C1 N1 C2 C3 83.4(7) . . . . ?
C6X N1 C2 C3 -113.0(9) . . . . ?
C6Y N1 C2 C3 -91.4(10) . . . . ?
N1 C2 C3 C4 175.0(5) . . . . ?
C2 C3 C4 C5 166.8(6) . . . . ?
N1 C1 C10 C11 -179.7(6) . . . . ?
S1 C1 C10 C11 0.5(8) . . . . ?
C1 C10 C11 C12 -0.3(9) . . . . ?
C10 C11 C12 C13 178.1(6) . . . . ?
C10 C11 C12 S1 0.0(7) . . . . ?
C1 S1 C12 C13 -177.8(6) . . . . ?
C1 S1 C12 C11 0.3(5) . . . . ?
C11 C12 C13 C14 -172.7(6) . . . . ?
S1 C12 C13 C14 5.1(10) . . . . ?
C12 C13 C14 C16 175.3(6) . . . . ?
C12 C13 C14 S2 1.2(10) . . . . ?
C15 S2 C14 C13 173.3(5) . . . . ?
C15 S2 C14 C16 -1.7(5) . . . . ?
C16 N2 C15 C21 178.8(6) . . . . ?
C16 N2 C15 S2 -1.4(7) . . . . ?
C14 S2 C15 N2 1.8(5) . . . . ?
C14 S2 C15 C21 -178.3(5) . . . . ?
C15 N2 C16 C14 -0.1(7) . . . . ?
C15 N2 C16 C17 -179.5(5) . . . . ?
C13 C14 C16 N2 -173.3(6) . . . . ?
S2 C14 C16 N2 1.4(7) . . . . ?
C13 C14 C16 C17 6.1(10) . . . . ?
S2 C14 C16 C17 -179.2(5) . . . . ?
N2 C16 C17 C20 -5.8(8) . . . . ?
C14 C16 C17 C20 174.9(6) . . . . ?
N2 C16 C17 C18 113.6(6) . . . . ?
C14 C16 C17 C18 -65.7(8) . . . . ?
N2 C16 C17 C19 -125.4(6) . . . . ?
C14 C16 C17 C19 55.3(8) . . . . ?
N2 C15 C21 C23 -2.0(10) . . . . ?
S2 C15 C21 C23 178.2(5) . . . . ?
N2 C15 C21 C22 -178.6(6) . . . . ?
S2 C15 C21 C22 1.6(9) . . . . ?
C1 N1 C6X C1X 73.7(16) . . . . ?
C2 N1 C6X C1X -89.2(15) . . . . ?
N1 C6X C1X C2X -171.3(14) . . . . ?
C6X C1X C2X C3X -60(2) . . . . ?
C1 N1 C6Y C1Y 84.5(11) . . . . ?
C2 N1 C6Y C1Y -100.3(12) . . . . ?
N1 C6Y C1Y C2Y -177.9(10) . . . . ?
C6Y C1Y C2Y C3Y -76.2(15) . . . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.094

####################################################################### 
# 
# 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_lb_tol_ol_sq
_database_code_depnum_ccdc_archive 'CCDC 2073461'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universitaet zu Koeln
Germany
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-06-23 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         'C23 H30 N4 S2 [+ solvent]'
_chemical_formula_sum            'C23 H30 N4 S2 [+ solvent]'
_chemical_formula_weight         426.63

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   38.067(3)
_cell_length_b                   10.0661(8)
_cell_length_c                   13.7086(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.303(3)
_cell_angle_gamma                90
_cell_volume                     5132.3(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9959
_cell_measurement_theta_min      4.55
_cell_measurement_theta_max      72.35

_exptl_crystal_description       irregular
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.983
_shelx_estimated_absorpt_T_min   0.890
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6322
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_detector_type            'Bruker PhotonIII M14'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33148
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.376
_diffrn_reflns_theta_max         72.344
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measured_fraction_theta_full 0.898
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_Laue_measured_fraction_full 0.898
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_point_group_measured_fraction_full 0.898
_reflns_number_total             4536
_reflns_number_gt                4081
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'

_refine_special_details          
'disordered solvent was refined using Platon SQUEEZE'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0707P)²+8.3175P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4536
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1415
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.002
_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 0.68428(2) 0.36402(5) 0.57548(4) 0.03081(17) Uani 1 1 d . . . . .
S2 S 0.75964(2) 0.20319(5) 0.63499(4) 0.02809(16) Uani 1 1 d . . . . .
N1 N 0.61534(6) 0.4420(2) 0.51703(19) 0.0517(7) Uani 1 1 d . . . . .
N2 N 0.82838(5) 0.24362(19) 0.68911(13) 0.0299(4) Uani 1 1 d . . . . .
N3 N 0.76247(7) -0.1654(2) 0.63354(17) 0.0481(6) Uani 1 1 d . . . . .
N4 N 0.87711(7) -0.0758(2) 0.71395(17) 0.0472(6) Uani 1 1 d . . . . .
C1 C 0.64916(7) 0.4788(2) 0.54653(17) 0.0354(5) Uani 1 1 d . . . . .
C2 C 0.66234(7) 0.6105(2) 0.55721(17) 0.0337(5) Uani 1 1 d . . . . .
H2 H 0.647336 0.686868 0.545974 0.040 Uiso 1 1 calc R U . . .
C3 C 0.69865(7) 0.6162(2) 0.58518(17) 0.0323(5) Uani 1 1 d . . . . .
H3 H 0.711371 0.697974 0.594422 0.039 Uiso 1 1 calc R U . . .
C4 C 0.71625(7) 0.4923(2) 0.59960(16) 0.0290(5) Uani 1 1 d . . . . .
C5 C 0.75297(6) 0.4788(2) 0.62850(16) 0.0301(5) Uani 1 1 d . . . . .
H5 H 0.765518 0.560929 0.637280 0.036 Uiso 1 1 calc R U . . .
C6 C 0.77538(7) 0.3677(2) 0.64745(16) 0.0294(5) Uani 1 1 d . . . . .
C7 C 0.81338(7) 0.3647(2) 0.67836(16) 0.0297(5) Uani 1 1 d . . . . .
C8 C 0.80376(6) 0.1470(2) 0.66864(15) 0.0277(5) Uani 1 1 d . . . . .
C9 C 0.81227(7) 0.0108(2) 0.67284(16) 0.0297(5) Uani 1 1 d . . . . .
C10 C 0.78499(7) -0.0867(2) 0.65103(17) 0.0344(5) Uani 1 1 d . . . . .
C11 C 0.84853(7) -0.0340(2) 0.69625(16) 0.0350(6) Uani 1 1 d . . . . .
C12 C 0.83788(7) 0.4866(2) 0.6998(2) 0.0391(6) Uani 1 1 d . . . . .
C13 C 0.82715(8) 0.5752(3) 0.7798(2) 0.0476(7) Uani 1 1 d . . . . .
H13A H 0.844036 0.649542 0.795027 0.071 Uiso 1 1 calc R U . . .
H13B H 0.827759 0.522949 0.840503 0.071 Uiso 1 1 calc R U . . .
H13C H 0.802793 0.609514 0.755023 0.071 Uiso 1 1 calc R U . . .
C14 C 0.83651(9) 0.5656(3) 0.6032(2) 0.0521(7) Uani 1 1 d . . . . .
H14A H 0.843781 0.508078 0.553274 0.078 Uiso 1 1 calc R U . . .
H14B H 0.852924 0.641544 0.617063 0.078 Uiso 1 1 calc R U . . .
H14C H 0.811961 0.597542 0.577570 0.078 Uiso 1 1 calc R U . . .
C15 C 0.87656(8) 0.4407(3) 0.7398(3) 0.0582(9) Uani 1 1 d . . . . .
H15A H 0.884221 0.383892 0.690137 0.087 Uiso 1 1 calc R U . . .
H15B H 0.877862 0.390516 0.801730 0.087 Uiso 1 1 calc R U . . .
H15C H 0.892398 0.518335 0.753202 0.087 Uiso 1 1 calc R U . . .
C16A C 0.5993(2) 0.3104(8) 0.5453(6) 0.047(2) Uani 0.403(6) 1 d . . P A 1
H16A H 0.618534 0.251251 0.581377 0.056 Uiso 0.403(6) 1 calc R U P A 1
H16B H 0.581967 0.327292 0.588399 0.056 Uiso 0.403(6) 1 calc R U P A 1
C17A C 0.5808(2) 0.2488(8) 0.4487(6) 0.056(2) Uani 0.403(6) 1 d . . P A 1
H17A H 0.597081 0.249167 0.401174 0.068 Uiso 0.403(6) 1 calc R U P A 1
H17B H 0.559092 0.300874 0.419050 0.068 Uiso 0.403(6) 1 calc R U P A 1
C18A C 0.5700(5) 0.105(2) 0.4673(11) 0.057(3) Uani 0.403(6) 1 d . . P A 1
H18A H 0.591875 0.048477 0.482446 0.069 Uiso 0.403(6) 1 calc R U P A 1
H18B H 0.558737 0.102558 0.525972 0.069 Uiso 0.403(6) 1 calc R U P A 1
C23A C 0.5453(3) 0.0509(13) 0.3818(12) 0.121(6) Uani 0.403(6) 1 d . . P A 1
H23A H 0.522252 0.097739 0.372899 0.181 Uiso 0.403(6) 1 calc R U P A 1
H23B H 0.541579 -0.043865 0.392516 0.181 Uiso 0.403(6) 1 calc R U P A 1
H23C H 0.555225 0.062391 0.322041 0.181 Uiso 0.403(6) 1 calc R U P A 1
C16B C 0.60692(11) 0.3009(4) 0.4817(4) 0.0338(11) Uani 0.597(6) 1 d . . P A 2
H16C H 0.629257 0.247448 0.492822 0.041 Uiso 0.597(6) 1 calc R U P A 2
H16D H 0.595899 0.300019 0.409427 0.041 Uiso 0.597(6) 1 calc R U P A 2
C17B C 0.58095(12) 0.2431(5) 0.5408(4) 0.0405(12) Uani 0.597(6) 1 d . . P A 2
H17C H 0.592897 0.240473 0.612355 0.049 Uiso 0.597(6) 1 calc R U P A 2
H17D H 0.559810 0.302427 0.533739 0.049 Uiso 0.597(6) 1 calc R U P A 2
C18B C 0.5683(4) 0.1054(16) 0.5075(9) 0.066(3) Uani 0.597(6) 1 d . . P A 2
H18C H 0.560876 0.104235 0.433737 0.079 Uiso 0.597(6) 1 calc R U P A 2
H18D H 0.588661 0.042762 0.526910 0.079 Uiso 0.597(6) 1 calc R U P A 2
C23B C 0.53893(16) 0.0605(7) 0.5490(6) 0.081(2) Uani 0.597(6) 1 d . . P A 2
H23D H 0.547382 0.044348 0.620685 0.122 Uiso 0.597(6) 1 calc R U P A 2
H23E H 0.529232 -0.022080 0.516009 0.122 Uiso 0.597(6) 1 calc R U P A 2
H23F H 0.520061 0.128428 0.538779 0.122 Uiso 0.597(6) 1 calc R U P A 2
C19 C 0.58692(8) 0.5430(3) 0.4957(3) 0.0590(9) Uani 1 1 d . . . . .
H19A H 0.565408 0.503779 0.451639 0.071 Uiso 1 1 calc R U . . .
H19B H 0.595218 0.617419 0.459063 0.071 Uiso 1 1 calc R U . . .
C20 C 0.57649(9) 0.5969(4) 0.5883(3) 0.0643(9) Uani 1 1 d . . . . .
H20A H 0.597953 0.636333 0.632391 0.077 Uiso 1 1 calc R U . . .
H20B H 0.568141 0.522600 0.624993 0.077 Uiso 1 1 calc R U . . .
C21 C 0.54706(12) 0.7012(5) 0.5651(3) 0.0872(13) Uani 1 1 d . . . . .
H21A H 0.526895 0.663046 0.515284 0.105 Uiso 0.6 1 d R U P . .
H21B H 0.556025 0.779566 0.534227 0.105 Uiso 1 1 d R U . . .
H21C H 0.541934 0.735899 0.627475 0.105 Uiso 0.4 1 d R U P . .
C22B C 0.5156(3) 0.6457(13) 0.5064(9) 0.094(4) Uani 0.4 1 d . . P . .
H22A H 0.519819 0.623601 0.440222 0.141 Uiso 0.4 1 calc R U P . .
H22B H 0.495919 0.710045 0.499528 0.141 Uiso 0.4 1 calc R U P . .
H22C H 0.509249 0.564981 0.538623 0.141 Uiso 0.4 1 calc R U P . .
C22A C 0.5311(2) 0.7479(8) 0.6589(6) 0.092(2) Uani 0.6 1 d . . P . .
H22D H 0.511619 0.811910 0.636654 0.138 Uiso 0.6 1 calc R U P . .
H22E H 0.550160 0.789807 0.708763 0.138 Uiso 0.6 1 calc R U P . .
H22F H 0.521710 0.670621 0.688615 0.138 Uiso 0.6 1 calc R U P . .


_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 C1 1.747(3) . ?
S1 C4 1.757(2) . ?
S2 C8 1.739(2) . ?
S2 C6 1.757(2) . ?
N1 C1 1.318(3) . ?
N1 C19 1.468(4) . ?
N1 C16B 1.513(5) . ?
N1 C16A 1.542(9) . ?
N2 C8 1.338(3) . ?
N2 C7 1.341(3) . ?
N3 C10 1.154(3) . ?
N4 C11 1.143(3) . ?
C1 C2 1.414(3) . ?
C2 C3 1.355(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(3) . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.418(3) . ?
C7 C12 1.531(3) . ?
C8 C9 1.408(3) . ?
C9 C10 1.414(3) . ?
C9 C11 1.422(4) . ?
C12 C15 1.529(4) . ?
C12 C13 1.535(4) . ?
C12 C14 1.536(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16A C17A 1.496(11) . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C17A C18A 1.54(2) . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C18A C23A 1.44(2) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C16B C17B 1.521(6) . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C17B C18B 1.506(16) . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C18B C23B 1.433(12) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
C19 C20 1.510(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.519(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22B 1.407(12) . ?
C21 C22A 1.606(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 H21C 0.9806 . ?
C22B H21A 0.4549 . ?
C22B H22A 0.9800 . ?
C22B H22B 0.9800 . ?
C22B H22C 0.9800 . ?
C22A H21C 0.6687 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?

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
C1 S1 C4 91.28(12) . . ?
C8 S2 C6 89.46(11) . . ?
C1 N1 C19 119.8(2) . . ?
C1 N1 C16B 119.2(3) . . ?
C19 N1 C16B 119.3(2) . . ?
C1 N1 C16A 125.3(3) . . ?
C19 N1 C16A 109.3(4) . . ?
C8 N2 C7 112.0(2) . . ?
N1 C1 C2 126.7(2) . . ?
N1 C1 S1 122.3(2) . . ?
C2 C1 S1 111.05(19) . . ?
C3 C2 C1 112.7(2) . . ?
C3 C2 H2 123.6 . . ?
C1 C2 H2 123.6 . . ?
C2 C3 C4 115.4(2) . . ?
C2 C3 H3 122.3 . . ?
C4 C3 H3 122.3 . . ?
C5 C4 C3 123.5(2) . . ?
C5 C4 S1 126.97(18) . . ?
C3 C4 S1 109.54(18) . . ?
C4 C5 C6 132.5(2) . . ?
C4 C5 H5 113.7 . . ?
C6 C5 H5 113.7 . . ?
C5 C6 C7 128.0(2) . . ?
C5 C6 S2 123.65(18) . . ?
C7 C6 S2 108.34(17) . . ?
N2 C7 C6 115.8(2) . . ?
N2 C7 C12 118.7(2) . . ?
C6 C7 C12 125.6(2) . . ?
N2 C8 C9 123.7(2) . . ?
N2 C8 S2 114.39(17) . . ?
C9 C8 S2 121.92(18) . . ?
C8 C9 C10 121.0(2) . . ?
C8 C9 C11 121.5(2) . . ?
C10 C9 C11 117.5(2) . . ?
N3 C10 C9 179.3(3) . . ?
N4 C11 C9 176.9(3) . . ?
C15 C12 C7 109.1(2) . . ?
C15 C12 C13 107.6(2) . . ?
C7 C12 C13 111.0(2) . . ?
C15 C12 C14 108.6(2) . . ?
C7 C12 C14 110.0(2) . . ?
C13 C12 C14 110.5(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17A C16A N1 105.7(6) . . ?
C17A C16A H16A 110.6 . . ?
N1 C16A H16A 110.6 . . ?
C17A C16A H16B 110.6 . . ?
N1 C16A H16B 110.6 . . ?
H16A C16A H16B 108.7 . . ?
C16A C17A C18A 109.6(8) . . ?
C16A C17A H17A 109.8 . . ?
C18A C17A H17A 109.8 . . ?
C16A C17A H17B 109.8 . . ?
C18A C17A H17B 109.8 . . ?
H17A C17A H17B 108.2 . . ?
C23A C18A C17A 111.6(13) . . ?
C23A C18A H18A 109.3 . . ?
C17A C18A H18A 109.3 . . ?
C23A C18A H18B 109.3 . . ?
C17A C18A H18B 109.3 . . ?
H18A C18A H18B 108.0 . . ?
C18A C23A H23A 109.5 . . ?
C18A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C18A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
N1 C16B C17B 107.8(4) . . ?
N1 C16B H16C 110.1 . . ?
C17B C16B H16C 110.1 . . ?
N1 C16B H16D 110.1 . . ?
C17B C16B H16D 110.1 . . ?
H16C C16B H16D 108.5 . . ?
C18B C17B C16B 113.1(5) . . ?
C18B C17B H17C 109.0 . . ?
C16B C17B H17C 109.0 . . ?
C18B C17B H17D 109.0 . . ?
C16B C17B H17D 109.0 . . ?
H17C C17B H17D 107.8 . . ?
C23B C18B C17B 113.3(8) . . ?
C23B C18B H18C 108.9 . . ?
C17B C18B H18C 108.9 . . ?
C23B C18B H18D 108.9 . . ?
C17B C18B H18D 108.9 . . ?
H18C C18B H18D 107.7 . . ?
C18B C23B H23D 109.5 . . ?
C18B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C18B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
N1 C19 C20 113.3(3) . . ?
N1 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
N1 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 C21 112.7(3) . . ?
C19 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C22B C21 C20 110.2(6) . . ?
C22B C21 C22A 98.8(6) . . ?
C20 C21 C22A 115.0(4) . . ?
C22B C21 H21A 8.8 . . ?
C20 C21 H21A 107.8 . . ?
C22A C21 H21A 107.2 . . ?
C22B C21 H21B 113.6 . . ?
C20 C21 H21B 109.6 . . ?
C22A C21 H21B 109.5 . . ?
H21A C21 H21B 107.5 . . ?
C22B C21 H21C 109.7 . . ?
C20 C21 H21C 109.8 . . ?
C22A C21 H21C 10.9 . . ?
H21A C21 H21C 118.1 . . ?
H21B C21 H21C 103.9 . . ?
C21 C22B H21A 19.4 . . ?
C21 C22B H22A 109.5 . . ?
H21A C22B H22A 90.2 . . ?
C21 C22B H22B 109.5 . . ?
H21A C22B H22B 115.6 . . ?
H22A C22B H22B 109.5 . . ?
C21 C22B H22C 109.5 . . ?
H21A C22B H22C 120.5 . . ?
H22A C22B H22C 109.5 . . ?
H22B C22B H22C 109.5 . . ?
C21 C22A H21C 16.1 . . ?
C21 C22A H22D 109.5 . . ?
H21C C22A H22D 116.6 . . ?
C21 C22A H22E 109.5 . . ?
H21C C22A H22E 93.4 . . ?
H22D C22A H22E 109.5 . . ?
C21 C22A H22F 109.5 . . ?
H21C C22A H22F 117.0 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?

_refine_diff_density_max         0.879
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.150



