# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_RS114_0m
_database_code_depnum_ccdc_archive 'CCDC 1984456'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University 
United States of America
;
_audit_update_record             
;
2020-02-15 deposited with the CCDC.	2020-06-01 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         'C8 N6, 2(C12 H28 N), 2(C N S)'
_chemical_formula_sum            'C34 H56 N10 S2'
_chemical_formula_weight         669.01

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                   9.6131(11)
_cell_length_b                   11.5468(13)
_cell_length_c                   17.891(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.086(7)
_cell_angle_gamma                90
_cell_volume                     1985.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9599
_cell_measurement_theta_min      4.5577
_cell_measurement_theta_max      80.6342

_exptl_crystal_description       fragment
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.487
_shelx_estimated_absorpt_T_min   0.736
_shelx_estimated_absorpt_T_max   0.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3690
_exptl_absorpt_correction_T_max  0.5260
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 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_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest CMOS diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            21437
_diffrn_reflns_av_unetI/netI     0.1059
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.470
_diffrn_reflns_theta_max         82.144
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4230
_reflns_number_gt                2898
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Apex3 v2018.7-2 (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 Rev946 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The structure emulates Pnnm symmetry and is twinned by this symmetry. 
The higher Pnnm symmetry is mostly obeyed, but broken by partial 
ordering of the thiocyanate ion. In the Pnnm setting, the anion is 
1:1 disordered around a two fold axis. In the actual P2(1)/n setting, 
the disorder is 0.685(5) to 0.315(5). Attempts to refine the structure 
in Pnnm resulted in R values around 12%, double the value of P2(1)/n. 
Splitting of reflections at high angle is also observed. 

The structure was refined as a 2-component twin, twin transformation 
matrix 1 0 0, 0 -1 0, 0 0 -1. The Flack parameter refined to 0.505(3). 

The two disordered thiocyanate 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 0.685(5) to 0.315(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)+(0.0857P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4230
_refine_ls_number_parameters     241
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1931
_refine_ls_wR_factor_gt          0.1720
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.047
_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 -0.0519(4) 0.1175(2) 0.3151(3) 0.0685(7) Uani 0.685(5) 1 d D U P A 1
C5 C 0.0126(6) -0.0149(4) 0.3194(3) 0.0595(12) Uani 0.685(5) 1 d D U P A 1
N4 N 0.0608(15) -0.1052(12) 0.3268(8) 0.077(3) Uani 0.685(5) 1 d D U P A 1
S1B S 0.0418(8) -0.1010(7) 0.3110(5) 0.0639(14) Uani 0.315(5) 1 d D U P A 2
C5B C -0.0155(13) 0.0348(8) 0.3170(7) 0.055(2) Uani 0.315(5) 1 d D U P A 2
N4B N -0.035(3) 0.1364(16) 0.318(2) 0.069(3) Uani 0.315(5) 1 d D U P A 2
N1 N 0.6287(2) 0.44138(17) 0.0014(2) 0.0556(6) Uani 1 1 d . . . . .
N2 N 0.5196(3) 0.1620(2) 0.0048(2) 0.0797(9) Uani 1 1 d . . . . .
N3 N 0.8538(3) 0.6666(2) 0.0016(3) 0.0780(8) Uani 1 1 d . . . . .
N25 N 0.4967(3) 0.01104(19) 0.25387(14) 0.0546(6) Uani 1 1 d . . . . .
C1 C 0.5076(3) 0.3857(2) 0.0012(2) 0.0552(6) Uani 1 1 d . . . . .
C2 C 0.5143(3) 0.2599(2) 0.0023(2) 0.0633(7) Uani 1 1 d . . . . .
C3 C 0.6198(3) 0.5565(2) 0.0005(3) 0.0557(6) Uani 1 1 d . . . . .
C4 C 0.7505(3) 0.6183(2) 0.0014(3) 0.0612(7) Uani 1 1 d . . . . .
C6 C 0.5093(4) -0.0972(2) 0.3013(2) 0.0599(9) Uani 1 1 d . . . . .
H6A H 0.426594 -0.102061 0.334019 0.072 Uiso 1 1 calc R U . . .
H6AB H 0.507338 -0.165328 0.267691 0.072 Uiso 1 1 calc R U . . .
C7 C 0.6366(4) -0.1050(3) 0.3492(3) 0.0773(13) Uani 1 1 d . . . . .
H7A H 0.630867 -0.047511 0.390102 0.093 Uiso 1 1 calc R U . . .
H7AB H 0.720052 -0.087237 0.318894 0.093 Uiso 1 1 calc R U . . .
C8 C 0.6492(4) -0.2261(3) 0.3818(2) 0.0702(10) Uani 1 1 d . . . . .
H8A H 0.652812 -0.282909 0.341207 0.105 Uiso 1 1 calc R U . . .
H8B H 0.568533 -0.242045 0.413630 0.105 Uiso 1 1 calc R U . . .
H8C H 0.734470 -0.231362 0.411766 0.105 Uiso 1 1 calc R U . . .
C9 C 0.6230(4) 0.0268(2) 0.2027(2) 0.0601(9) Uani 1 1 d . . . . .
H9A H 0.604201 0.092828 0.168873 0.072 Uiso 1 1 calc R U . . .
H9AB H 0.703903 0.047994 0.234104 0.072 Uiso 1 1 calc R U . . .
C10 C 0.6630(4) -0.0771(3) 0.1553(3) 0.0847(14) Uani 1 1 d . . . . .
H10A H 0.583171 -0.100006 0.123537 0.102 Uiso 1 1 calc R U . . .
H10B H 0.686501 -0.143200 0.188162 0.102 Uiso 1 1 calc R U . . .
C11 C 0.7872(5) -0.0484(3) 0.1059(3) 0.0812(12) Uani 1 1 d . . . . .
H11A H 0.812968 -0.116801 0.076654 0.122 Uiso 1 1 calc R U . . .
H11B H 0.865962 -0.025007 0.137365 0.122 Uiso 1 1 calc R U . . .
H11C H 0.762723 0.015143 0.072069 0.122 Uiso 1 1 calc R U . . .
C12 C 0.3654(3) -0.0032(2) 0.2087(2) 0.0581(9) Uani 1 1 d . . . . .
H12A H 0.380843 -0.065416 0.171558 0.070 Uiso 1 1 calc R U . . .
H12B H 0.290626 -0.029591 0.242678 0.070 Uiso 1 1 calc R U . . .
C13 C 0.3148(4) 0.1028(3) 0.1679(3) 0.0765(13) Uani 1 1 d . . . . .
H13A H 0.285952 0.162615 0.204402 0.092 Uiso 1 1 calc R U . . .
H13B H 0.390831 0.135098 0.137040 0.092 Uiso 1 1 calc R U . . .
C14 C 0.1934(5) 0.0709(3) 0.1188(3) 0.0797(13) Uani 1 1 d . . . . .
H14A H 0.155782 0.140939 0.095338 0.120 Uiso 1 1 calc R U . . .
H14B H 0.121066 0.034008 0.149073 0.120 Uiso 1 1 calc R U . . .
H14C H 0.224469 0.016988 0.079919 0.120 Uiso 1 1 calc R U . . .
C15 C 0.4903(3) 0.1185(2) 0.3028(2) 0.0573(9) Uani 1 1 d . . . . .
H15A H 0.482810 0.187053 0.269842 0.069 Uiso 1 1 calc R U . . .
H15B H 0.579322 0.124930 0.330367 0.069 Uiso 1 1 calc R U . . .
C16 C 0.3714(4) 0.1234(3) 0.3596(2) 0.0668(10) Uani 1 1 d . . . . .
H16A H 0.283421 0.098703 0.335590 0.080 Uiso 1 1 calc R U . . .
H16B H 0.391091 0.070042 0.401650 0.080 Uiso 1 1 calc R U . . .
C17 C 0.3567(4) 0.2466(3) 0.3888(2) 0.0726(11) Uani 1 1 d . . . . .
H17A H 0.339666 0.299316 0.346865 0.109 Uiso 1 1 calc R U . . .
H17B H 0.442549 0.269331 0.414555 0.109 Uiso 1 1 calc R U . . .
H17C H 0.278552 0.250473 0.423817 0.109 Uiso 1 1 calc R 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
S1 C5 1.651(6) . ?
C5 N4 1.148(13) . ?
S1B C5B 1.666(11) . ?
C5B N4B 1.189(17) . ?
N1 C1 1.330(3) . ?
N1 C3 1.333(3) . ?
N2 C2 1.132(3) . ?
N3 C4 1.139(3) . ?
N25 C12 1.506(4) . ?
N25 C6 1.515(4) . ?
N25 C15 1.520(4) . ?
N25 C9 1.532(5) . ?
C1 C3 1.394(4) 3_665 ?
C1 C2 1.454(3) . ?
C3 C4 1.445(4) . ?
C6 C7 1.496(5) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.520(5) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.519(5) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C11 1.522(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.506(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.506(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.532(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.522(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
N4 C5 S1 175.6(8) . . ?
N4B C5B S1B 169.5(18) . . ?
C1 N1 C3 115.2(2) . . ?
C12 N25 C6 106.0(2) . . ?
C12 N25 C15 111.3(2) . . ?
C6 N25 C15 110.7(2) . . ?
C12 N25 C9 110.9(2) . . ?
C6 N25 C9 111.7(2) . . ?
C15 N25 C9 106.3(2) . . ?
N1 C1 C3 122.5(2) . 3_665 ?
N1 C1 C2 116.3(2) . . ?
C3 C1 C2 121.1(2) 3_665 . ?
N2 C2 C1 178.6(5) . . ?
N1 C3 C1 122.3(2) . 3_665 ?
N1 C3 C4 115.9(2) . . ?
C1 C3 C4 121.8(2) 3_665 . ?
N3 C4 C3 179.6(6) . . ?
C7 C6 N25 115.8(3) . . ?
C7 C6 H6A 108.3 . . ?
N25 C6 H6A 108.3 . . ?
C7 C6 H6AB 108.3 . . ?
N25 C6 H6AB 108.3 . . ?
H6A C6 H6AB 107.4 . . ?
C6 C7 C8 109.9(3) . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7AB 109.7 . . ?
C8 C7 H7AB 109.7 . . ?
H7A C7 H7AB 108.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N25 116.2(3) . . ?
C10 C9 H9A 108.2 . . ?
N25 C9 H9A 108.2 . . ?
C10 C9 H9AB 108.2 . . ?
N25 C9 H9AB 108.2 . . ?
H9A C9 H9AB 107.4 . . ?
C9 C10 C11 110.6(3) . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N25 116.2(2) . . ?
C13 C12 H12A 108.2 . . ?
N25 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
N25 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
C14 C13 C12 109.5(3) . . ?
C14 C13 H13A 109.8 . . ?
C12 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N25 C15 C16 116.3(2) . . ?
N25 C15 H15A 108.2 . . ?
C16 C15 H15A 108.2 . . ?
N25 C15 H15B 108.2 . . ?
C16 C15 H15B 108.2 . . ?
H15A C15 H15B 107.4 . . ?
C17 C16 C15 109.4(3) . . ?
C17 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C3 N1 C1 C3 0.5(6) . . . 3_665 ?
C3 N1 C1 C2 -179.9(4) . . . . ?
C1 N1 C3 C1 -0.5(6) . . . 3_665 ?
C1 N1 C3 C4 179.5(5) . . . . ?
C12 N25 C6 C7 177.6(4) . . . . ?
C15 N25 C6 C7 -61.6(4) . . . . ?
C9 N25 C6 C7 56.7(4) . . . . ?
N25 C6 C7 C8 -169.4(3) . . . . ?
C12 N25 C9 C10 -66.8(4) . . . . ?
C6 N25 C9 C10 51.2(4) . . . . ?
C15 N25 C9 C10 172.1(3) . . . . ?
N25 C9 C10 C11 178.5(3) . . . . ?
C6 N25 C12 C13 168.6(4) . . . . ?
C15 N25 C12 C13 48.1(4) . . . . ?
C9 N25 C12 C13 -70.0(4) . . . . ?
N25 C12 C13 C14 173.4(4) . . . . ?
C12 N25 C15 C16 59.3(4) . . . . ?
C6 N25 C15 C16 -58.4(4) . . . . ?
C9 N25 C15 C16 -179.9(3) . . . . ?
N25 C15 C16 C17 -165.2(3) . . . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_RS95_0m
_database_code_depnum_ccdc_archive 'CCDC 1984457'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University 
United States of America
;
_audit_update_record             
;
2020-02-15 deposited with the CCDC.	2020-06-01 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         'C12 H28 N, 1.5(C6 F4 O2), C N S'
_chemical_formula_sum            'C22 H28 F6 N2 O3 S'
_chemical_formula_weight         514.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   10.2809(17)
_cell_length_b                   24.653(4)
_cell_length_c                   9.7480(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.110(6)
_cell_angle_gamma                90
_cell_volume                     2470.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9981
_cell_measurement_theta_min      2.5806
_cell_measurement_theta_max      30.5674

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.202
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6197
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            28882
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.478
_diffrn_reflns_theta_max         30.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             7332
_reflns_number_gt                5827
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Apex3 v2018.1-0 (Bruker, 2018)'
_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 Rev946 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The structure is metrically orthorhombic but actually monoclinic and 
twinned by a 180 rotation around the a or c-axis. Application of the 
transformation matrix 1 0 0 , 0 -1 0, 0 0 -1 yielded a twin ratio 
of 0.561(1) to 0.439(1).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²+0.3329P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0103(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7332
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
C1 C 0.8854(2) 0.19741(8) 0.1388(2) 0.0367(4) Uani 1 1 d . . . . .
C2 C 0.92015(18) 0.24556(8) 0.0587(2) 0.0355(4) Uani 1 1 d . . . . .
C3 C 1.0419(2) 0.25878(7) 0.03381(19) 0.0338(4) Uani 1 1 d . . . . .
C4 C 1.15341(18) 0.22594(8) 0.08470(19) 0.0303(4) Uani 1 1 d . . . . .
C5 C 1.1177(2) 0.17558(7) 0.15591(18) 0.0312(4) Uani 1 1 d . . . . .
C6 C 0.9960(2) 0.16270(7) 0.18076(19) 0.0322(4) Uani 1 1 d . . . . .
C7 C 0.8678(2) 0.50371(7) 0.4458(2) 0.0359(4) Uani 1 1 d . . . . .
C8 C 0.8977(2) 0.50001(8) 0.5943(2) 0.0375(4) Uani 1 1 d . . . . .
C9 C 1.0187(2) 0.49768(8) 0.6442(2) 0.0366(4) Uani 1 1 d . . . . .
C10 C 0.9801(2) 0.36407(8) 0.3634(2) 0.0352(4) Uani 1 1 d . . . . .
C11 C 0.47103(16) 0.31460(6) 0.27686(17) 0.0243(3) Uani 1 1 d . . . . .
H11A H 0.446637 0.300220 0.185545 0.029 Uiso 1 1 calc R U . . .
H11B H 0.391295 0.315344 0.333616 0.029 Uiso 1 1 calc R U . . .
C12 C 0.56815(18) 0.27543(7) 0.3430(2) 0.0302(4) Uani 1 1 d . . . . .
H12A H 0.651260 0.275973 0.291864 0.036 Uiso 1 1 calc R U . . .
H12B H 0.585744 0.286443 0.438901 0.036 Uiso 1 1 calc R U . . .
C13 C 0.5098(2) 0.21862(7) 0.3398(2) 0.0339(4) Uani 1 1 d . . . . .
H13A H 0.573584 0.192501 0.374793 0.051 Uiso 1 1 calc R U . . .
H13B H 0.486462 0.209159 0.245256 0.051 Uiso 1 1 calc R U . . .
H13C H 0.431730 0.217660 0.397321 0.051 Uiso 1 1 calc R U . . .
C14 C 0.40885(17) 0.40645(6) 0.19888(19) 0.0262(3) Uani 1 1 d . . . . .
H14A H 0.438767 0.444554 0.193107 0.031 Uiso 1 1 calc R U . . .
H14B H 0.335099 0.405512 0.263993 0.031 Uiso 1 1 calc R U . . .
C15 C 0.3580(2) 0.38973(7) 0.05754(19) 0.0310(4) Uani 1 1 d . . . . .
H15A H 0.322202 0.352492 0.062056 0.037 Uiso 1 1 calc R U . . .
H15B H 0.430334 0.389846 -0.009332 0.037 Uiso 1 1 calc R U . . .
C16 C 0.2516(2) 0.42916(8) 0.0102(2) 0.0429(5) Uani 1 1 d . . . . .
H16A H 0.177794 0.427285 0.073485 0.064 Uiso 1 1 calc R U . . .
H16B H 0.222668 0.419211 -0.082293 0.064 Uiso 1 1 calc R U . . .
H16C H 0.286374 0.466166 0.009137 0.064 Uiso 1 1 calc R U . . .
C17 C 0.63476(17) 0.37104(6) 0.16424(18) 0.0271(3) Uani 1 1 d . . . . .
H17A H 0.612336 0.347816 0.084789 0.032 Uiso 1 1 calc R U . . .
H17B H 0.707857 0.353398 0.213175 0.032 Uiso 1 1 calc R U . . .
C18 C 0.6818(2) 0.42532(7) 0.1102(2) 0.0341(4) Uani 1 1 d . . . . .
H18A H 0.612062 0.443176 0.056563 0.041 Uiso 1 1 calc R U . . .
H18B H 0.706079 0.449376 0.187454 0.041 Uiso 1 1 calc R U . . .
C19 C 0.7988(2) 0.41484(8) 0.0200(2) 0.0429(5) Uani 1 1 d . . . . .
H19A H 0.867686 0.397645 0.074397 0.064 Uiso 1 1 calc R U . . .
H19B H 0.830708 0.449295 -0.017154 0.064 Uiso 1 1 calc R U . . .
H19C H 0.773905 0.390796 -0.055674 0.064 Uiso 1 1 calc R U . . .
C20 C 0.56359(17) 0.39691(7) 0.39602(18) 0.0256(3) Uani 1 1 d . . . . .
H20A H 0.643313 0.377797 0.426310 0.031 Uiso 1 1 calc R U . . .
H20B H 0.586880 0.435407 0.380781 0.031 Uiso 1 1 calc R U . . .
C21 C 0.46515(18) 0.39417(8) 0.50961(18) 0.0307(4) Uani 1 1 d . . . . .
H21A H 0.443706 0.355857 0.529939 0.037 Uiso 1 1 calc R U . . .
H21B H 0.384277 0.412946 0.481441 0.037 Uiso 1 1 calc R U . . .
C22 C 0.5227(2) 0.42163(9) 0.6384(2) 0.0379(4) Uani 1 1 d . . . . .
H22A H 0.458601 0.420708 0.712617 0.057 Uiso 1 1 calc R U . . .
H22B H 0.544661 0.459386 0.617160 0.057 Uiso 1 1 calc R U . . .
H22C H 0.601363 0.402232 0.667098 0.057 Uiso 1 1 calc R U . . .
N1 N 0.88701(19) 0.38073(8) 0.4034(2) 0.0472(5) Uani 1 1 d . . . . .
N2 N 0.51937(14) 0.37253(5) 0.25923(14) 0.0228(3) Uani 1 1 d . . . . .
O1 O 0.77481(15) 0.18785(7) 0.1718(2) 0.0577(5) Uani 1 1 d . . . . .
O2 O 1.26513(13) 0.24080(7) 0.07482(16) 0.0434(4) Uani 1 1 d . . . . .
O3 O 0.75836(14) 0.50935(6) 0.4010(2) 0.0492(4) Uani 1 1 d . . . . .
S1 S 1.11671(6) 0.33843(2) 0.31025(6) 0.04349(14) Uani 1 1 d . . . . .
F1 F 0.82045(14) 0.27629(6) 0.01493(18) 0.0598(4) Uani 1 1 d . . . . .
F2 F 1.07218(15) 0.30336(5) -0.03492(13) 0.0518(4) Uani 1 1 d . . . . .
F3 F 1.21730(13) 0.14469(6) 0.19808(14) 0.0487(3) Uani 1 1 d . . . . .
F4 F 0.96636(15) 0.11787(5) 0.24960(14) 0.0518(4) Uani 1 1 d . . . . .
F5 F 0.79547(14) 0.50058(6) 0.67561(17) 0.0566(4) Uani 1 1 d . . . . .
F6 F 1.04489(15) 0.49583(6) 0.77832(14) 0.0540(4) 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
C1 O1 1.205(2) . ?
C1 C2 1.465(3) . ?
C1 C6 1.480(3) . ?
C2 C3 1.316(3) . ?
C2 F1 1.343(2) . ?
C3 F2 1.325(2) . ?
C3 C4 1.488(3) . ?
C4 O2 1.210(2) . ?
C4 C5 1.469(3) . ?
C5 C6 1.313(3) . ?
C5 F3 1.340(2) . ?
C6 F4 1.329(2) . ?
C7 O3 1.215(3) . ?
C7 C9 1.462(3) 3_766 ?
C7 C8 1.482(3) . ?
C8 F5 1.318(2) . ?
C8 C9 1.335(3) . ?
C9 F6 1.335(3) . ?
C10 N1 1.113(3) . ?
C10 S1 1.626(2) . ?
C11 N2 1.522(2) . ?
C11 C12 1.531(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.524(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N2 1.528(2) . ?
C14 C15 1.529(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.534(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N2 1.507(2) . ?
C17 C18 1.517(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.514(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.503(2) . ?
C20 N2 1.531(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.543(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
O1 C1 C2 122.1(2) . . ?
O1 C1 C6 122.5(2) . . ?
C2 C1 C6 115.29(16) . . ?
C3 C2 F1 121.79(19) . . ?
C3 C2 C1 122.13(18) . . ?
F1 C2 C1 116.05(18) . . ?
C2 C3 F2 121.56(19) . . ?
C2 C3 C4 122.43(17) . . ?
F2 C3 C4 115.99(17) . . ?
O2 C4 C5 122.13(18) . . ?
O2 C4 C3 122.68(18) . . ?
C5 C4 C3 115.08(16) . . ?
C6 C5 F3 122.24(17) . . ?
C6 C5 C4 122.04(17) . . ?
F3 C5 C4 115.68(17) . . ?
C5 C6 F4 120.91(19) . . ?
C5 C6 C1 122.74(16) . . ?
F4 C6 C1 116.32(17) . . ?
O3 C7 C9 121.8(2) . 3_766 ?
O3 C7 C8 123.3(2) . . ?
C9 C7 C8 114.88(18) 3_766 . ?
F5 C8 C9 121.7(2) . . ?
F5 C8 C7 115.00(19) . . ?
C9 C8 C7 123.32(19) . . ?
C8 C9 F6 122.9(2) . . ?
C8 C9 C7 121.8(2) . 3_766 ?
F6 C9 C7 115.30(19) . 3_766 ?
N1 C10 S1 177.86(19) . . ?
N2 C11 C12 115.26(14) . . ?
N2 C11 H11A 108.5 . . ?
C12 C11 H11A 108.5 . . ?
N2 C11 H11B 108.5 . . ?
C12 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 108.34(15) . . ?
C13 C12 H12A 110.0 . . ?
C11 C12 H12A 110.0 . . ?
C13 C12 H12B 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
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 . . ?
N2 C14 C15 116.88(13) . . ?
N2 C14 H14A 108.1 . . ?
C15 C14 H14A 108.1 . . ?
N2 C14 H14B 108.1 . . ?
C15 C14 H14B 108.1 . . ?
H14A C14 H14B 107.3 . . ?
C14 C15 C16 110.04(15) . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C18 116.33(13) . . ?
N2 C17 H17A 108.2 . . ?
C18 C17 H17A 108.2 . . ?
N2 C17 H17B 108.2 . . ?
C18 C17 H17B 108.2 . . ?
H17A C17 H17B 107.4 . . ?
C19 C18 C17 107.78(15) . . ?
C19 C18 H18A 110.2 . . ?
C17 C18 H18A 110.2 . . ?
C19 C18 H18B 110.2 . . ?
C17 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 N2 115.13(14) . . ?
C21 C20 H20A 108.5 . . ?
N2 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
N2 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C20 C21 C22 108.77(15) . . ?
C20 C21 H21A 109.9 . . ?
C22 C21 H21A 109.9 . . ?
C20 C21 H21B 109.9 . . ?
C22 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 N2 C11 107.71(12) . . ?
C17 N2 C14 111.26(13) . . ?
C11 N2 C14 108.32(13) . . ?
C17 N2 C20 108.18(13) . . ?
C11 N2 C20 111.50(12) . . ?
C14 N2 C20 109.87(12) . . ?

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
O1 C1 C2 C3 173.4(2) . . . . ?
C6 C1 C2 C3 -4.3(3) . . . . ?
O1 C1 C2 F1 -5.0(3) . . . . ?
C6 C1 C2 F1 177.33(16) . . . . ?
F1 C2 C3 F2 0.5(3) . . . . ?
C1 C2 C3 F2 -177.76(17) . . . . ?
F1 C2 C3 C4 178.37(18) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 O2 -171.95(19) . . . . ?
F2 C3 C4 O2 6.0(3) . . . . ?
C2 C3 C4 C5 4.3(3) . . . . ?
F2 C3 C4 C5 -177.70(16) . . . . ?
O2 C4 C5 C6 171.79(19) . . . . ?
C3 C4 C5 C6 -4.5(3) . . . . ?
O2 C4 C5 F3 -5.9(3) . . . . ?
C3 C4 C5 F3 177.77(16) . . . . ?
F3 C5 C6 F4 0.0(3) . . . . ?
C4 C5 C6 F4 -177.60(16) . . . . ?
F3 C5 C6 C1 177.89(18) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
O1 C1 C6 C5 -173.5(2) . . . . ?
C2 C1 C6 C5 4.1(3) . . . . ?
O1 C1 C6 F4 4.5(3) . . . . ?
C2 C1 C6 F4 -177.85(16) . . . . ?
O3 C7 C8 F5 3.2(3) . . . . ?
C9 C7 C8 F5 -179.20(16) 3_766 . . . ?
O3 C7 C8 C9 -175.08(19) . . . . ?
C9 C7 C8 C9 2.5(3) 3_766 . . . ?
F5 C8 C9 F6 -0.1(3) . . . . ?
C7 C8 C9 F6 178.14(16) . . . . ?
F5 C8 C9 C7 179.15(17) . . . 3_766 ?
C7 C8 C9 C7 -2.7(3) . . . 3_766 ?
N2 C11 C12 C13 -174.44(14) . . . . ?
N2 C14 C15 C16 -177.80(16) . . . . ?
N2 C17 C18 C19 178.90(18) . . . . ?
N2 C20 C21 C22 -178.45(15) . . . . ?
C18 C17 N2 C11 168.31(16) . . . . ?
C18 C17 N2 C14 49.7(2) . . . . ?
C18 C17 N2 C20 -71.0(2) . . . . ?
C12 C11 N2 C17 62.32(18) . . . . ?
C12 C11 N2 C14 -177.23(14) . . . . ?
C12 C11 N2 C20 -56.22(18) . . . . ?
C15 C14 N2 C17 56.74(18) . . . . ?
C15 C14 N2 C11 -61.47(18) . . . . ?
C15 C14 N2 C20 176.52(14) . . . . ?
C21 C20 N2 C17 -171.71(14) . . . . ?
C21 C20 N2 C11 -53.45(19) . . . . ?
C21 C20 N2 C14 66.65(18) . . . . ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_RS130A_0m
_database_code_depnum_ccdc_archive 'CCDC 1984459'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University 
United States of America
;
_audit_update_record             
;
2020-02-15 deposited with the CCDC.	2020-06-01 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         '2(C12 H28 N), (C6 N4), 2(C N S)'
_chemical_formula_sum            'C32 H56 N8 S2'
_chemical_formula_weight         616.96

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      tetragonal
_space_group_IT_number           122
_space_group_name_H-M_alt        'I -4 2 d'
_space_group_name_Hall           'I -4 2bw'

_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'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y, -z+3/4'
'x+1/2, -y, -z+3/4'
'-y+1/2, -x, z+3/4'
'y+1/2, x, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'-x+1, y+1/2, -z+5/4'
'x+1, -y+1/2, -z+5/4'
'-y+1, -x+1/2, z+5/4'
'y+1, x+1/2, z+5/4'

_cell_length_a                   14.7446(7)
_cell_length_b                   14.7446
_cell_length_c                   34.4695(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7493.8(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9810
_cell_measurement_theta_min      2.2831
_cell_measurement_theta_max      32.5447

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_F_000             2688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7111
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_reflns_number            45869
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.247
_diffrn_reflns_theta_max         33.191
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7026
_reflns_number_gt                5227
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_max     0.952
_reflns_Friedel_fraction_full    0.996

_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 v2018.1-0 (Bruker, 2018)'
_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 Rev988 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The isocyanate ions are 1:1 disordered around a two fold axis (that 
coincides with a four-fold rotinversion axis). Uij components of ADPs 
for disordered atoms closer to each other than 2.7 Angstrom were 
restrained to be similar. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0697P)²+0.2330P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1916 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(18)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7026
_refine_ls_number_parameters     222
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.047
_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 -0.03557(14) -0.08111(16) 0.16147(6) 0.0389(3) Uani 0.5 1 d . U P A -1
C16 C 0.0039(3) 0.0238(2) 0.16212(10) 0.0375(9) Uani 0.5 1 d . U P A -1
N5 N 0.0245(6) 0.0982(6) 0.1642(3) 0.079(3) Uani 0.5 1 d . U P A -1
S2 S -0.03026(16) -0.07709(14) 0.34552(7) 0.0400(3) Uani 0.5 1 d . U P B -1
C17 C 0.0034(3) 0.0278(3) 0.34295(9) 0.0343(7) Uani 0.5 1 d . U P B -1
N6 N 0.0231(6) 0.1036(4) 0.3394(2) 0.0496(18) Uani 0.5 1 d . U P B -1
N1 N 0.17840(10) 0.09825(10) 0.25656(5) 0.0434(3) Uani 1 1 d . . . . .
N2 N -0.10862(11) 0.17141(10) 0.25358(5) 0.0477(4) Uani 1 1 d . . . . .
N3 N 0.30706(12) 0.250000 0.125000 0.0335(4) Uani 1 2 d S T P . .
N4 N 0.250000 0.29382(11) 0.375000 0.0325(4) Uani 1 2 d S T P . .
C1 C 0.01179(10) 0.04465(10) 0.25432(4) 0.0298(3) Uani 1 1 d . . . . .
C2 C 0.10501(10) 0.07332(10) 0.25529(5) 0.0331(3) Uani 1 1 d . . . . .
C3 C -0.05560(11) 0.11499(10) 0.25411(5) 0.0356(3) Uani 1 1 d . . . . .
C4 C 0.24849(11) 0.30660(10) 0.15214(5) 0.0359(3) Uani 1 1 d . . . . .
H4A H 0.288107 0.349806 0.166141 0.043 Uiso 1 1 calc R U . . .
H4B H 0.205574 0.342594 0.136298 0.043 Uiso 1 1 calc R U . . .
C5 C 0.19473(14) 0.25271(13) 0.18172(7) 0.0524(5) Uani 1 1 d . . . . .
H5A H 0.167899 0.198691 0.169105 0.063 Uiso 1 1 calc R U . . .
H5B H 0.235679 0.231645 0.202623 0.063 Uiso 1 1 calc R U . . .
C6 C 0.12008(15) 0.31057(15) 0.19893(7) 0.0569(5) Uani 1 1 d . . . . .
H6A H 0.146859 0.363167 0.212009 0.085 Uiso 1 1 calc R U . . .
H6B H 0.085471 0.274663 0.217728 0.085 Uiso 1 1 calc R U . . .
H6C H 0.079594 0.331334 0.178212 0.085 Uiso 1 1 calc R U . . .
C7 C 0.36510(11) 0.18354(11) 0.14756(5) 0.0390(4) Uani 1 1 d . . . . .
H7A H 0.400620 0.147414 0.128715 0.047 Uiso 1 1 calc R U . . .
H7B H 0.324165 0.141132 0.161317 0.047 Uiso 1 1 calc R U . . .
C8 C 0.43047(13) 0.22309(13) 0.17701(6) 0.0495(4) Uani 1 1 d . . . . .
H8A H 0.397494 0.263162 0.195230 0.059 Uiso 1 1 calc R U . . .
H8B H 0.477454 0.259497 0.163649 0.059 Uiso 1 1 calc R U . . .
C9 C 0.47464(17) 0.14525(16) 0.19912(7) 0.0657(6) Uani 1 1 d . . . . .
H9A H 0.427988 0.111245 0.213212 0.099 Uiso 1 1 calc R U . . .
H9B H 0.518916 0.169622 0.217582 0.099 Uiso 1 1 calc R U . . .
H9C H 0.505403 0.104827 0.180787 0.099 Uiso 1 1 calc R U . . .
C10 C 0.19841(11) 0.35609(10) 0.34751(5) 0.0340(3) Uani 1 1 d . . . . .
H10A H 0.159439 0.396548 0.363241 0.041 Uiso 1 1 calc R U . . .
H10B H 0.242987 0.394842 0.333848 0.041 Uiso 1 1 calc R U . . .
C11 C 0.13917(13) 0.30997(12) 0.31719(6) 0.0452(4) Uani 1 1 d . . . . .
H11A H 0.177717 0.282903 0.296717 0.054 Uiso 1 1 calc R U . . .
H11B H 0.103446 0.260827 0.329414 0.054 Uiso 1 1 calc R U . . .
C12 C 0.07602(14) 0.37954(17) 0.29954(7) 0.0586(5) Uani 1 1 d . . . . .
H12A H 0.039473 0.407493 0.320052 0.088 Uiso 1 1 calc R U . . .
H12B H 0.035951 0.349807 0.280753 0.088 Uiso 1 1 calc R U . . .
H12C H 0.111741 0.426384 0.286368 0.088 Uiso 1 1 calc R U . . .
C13 C 0.31411(12) 0.23195(10) 0.35275(6) 0.0401(4) Uani 1 1 d . . . . .
H13A H 0.337297 0.185179 0.370814 0.048 Uiso 1 1 calc R U . . .
H13B H 0.278992 0.200371 0.332339 0.048 Uiso 1 1 calc R U . . .
C14 C 0.39463(12) 0.27853(11) 0.33379(6) 0.0463(4) Uani 1 1 d . . . . .
H14A H 0.373532 0.331429 0.318581 0.056 Uiso 1 1 calc R U . . .
H14B H 0.436997 0.300501 0.353993 0.056 Uiso 1 1 calc R U . . .
C15 C 0.44288(16) 0.21207(14) 0.30735(7) 0.0617(6) Uani 1 1 d . . . . .
H15A H 0.460615 0.158300 0.322240 0.092 Uiso 1 1 calc R U . . .
H15B H 0.497105 0.240858 0.296457 0.092 Uiso 1 1 calc R U . . .
H15C H 0.402115 0.194082 0.286253 0.092 Uiso 1 1 calc R 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
S1 C16 1.653(4) . ?
C16 N5 1.140(10) . ?
S2 C17 1.627(5) . ?
C17 N6 1.161(7) . ?
N1 C2 1.144(2) . ?
N2 C3 1.142(2) . ?
N3 C7 1.5156(19) 14_454 ?
N3 C7 1.5157(19) . ?
N3 C4 1.5222(18) . ?
N3 C4 1.5223(18) 14_454 ?
N4 C13 1.5210(18) . ?
N4 C13 1.5211(18) 5 ?
N4 C10 1.5231(19) . ?
N4 C10 1.5232(19) 5 ?
C1 C1 1.362(3) 2 ?
C1 C3 1.436(2) . ?
C1 C2 1.438(2) . ?
C4 C5 1.516(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.514(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.516(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.524(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.522(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.513(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.519(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.516(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
N5 C16 S1 174.1(6) . . ?
N6 C17 S2 175.6(5) . . ?
C7 N3 C7 111.25(18) 14_454 . ?
C7 N3 C4 106.33(8) 14_454 . ?
C7 N3 C4 111.07(10) . . ?
C7 N3 C4 111.07(10) 14_454 14_454 ?
C7 N3 C4 106.33(8) . 14_454 ?
C4 N3 C4 110.87(17) . 14_454 ?
C13 N4 C13 106.30(15) . 5 ?
C13 N4 C10 110.99(10) . . ?
C13 N4 C10 111.40(9) 5 . ?
C13 N4 C10 111.40(9) . 5 ?
C13 N4 C10 110.99(10) 5 5 ?
C10 N4 C10 105.85(15) . 5 ?
C1 C1 C3 121.43(17) 2 . ?
C1 C1 C2 121.88(16) 2 . ?
C3 C1 C2 116.68(13) . . ?
N1 C2 C1 178.11(18) . . ?
N2 C3 C1 179.2(2) . . ?
C5 C4 N3 114.99(12) . . ?
C5 C4 H4A 108.5 . . ?
N3 C4 H4A 108.5 . . ?
C5 C4 H4B 108.5 . . ?
N3 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
C6 C5 C4 110.39(16) . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 C8 116.98(13) . . ?
N3 C7 H7A 108.1 . . ?
C8 C7 H7A 108.1 . . ?
N3 C7 H7B 108.1 . . ?
C8 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C7 C8 C9 108.47(15) . . ?
C7 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
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 N4 116.38(13) . . ?
C11 C10 H10A 108.2 . . ?
N4 C10 H10A 108.2 . . ?
C11 C10 H10B 108.2 . . ?
N4 C10 H10B 108.2 . . ?
H10A C10 H10B 107.3 . . ?
C12 C11 C10 109.04(14) . . ?
C12 C11 H11A 109.9 . . ?
C10 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
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 N4 115.56(12) . . ?
C14 C13 H13A 108.4 . . ?
N4 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
N4 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 109.47(14) . . ?
C15 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C7 N3 C4 C5 -171.44(16) 14_454 . . . ?
C7 N3 C4 C5 -50.27(19) . . . . ?
C4 N3 C4 C5 67.72(14) 14_454 . . . ?
N3 C4 C5 C6 -163.64(16) . . . . ?
C7 N3 C7 C8 58.94(14) 14_454 . . . ?
C4 N3 C7 C8 -59.3(2) . . . . ?
C4 N3 C7 C8 179.99(15) 14_454 . . . ?
N3 C7 C8 C9 174.30(17) . . . . ?
C13 N4 C10 C11 60.12(16) . . . . ?
C13 N4 C10 C11 -58.12(17) 5 . . . ?
C10 N4 C10 C11 -178.87(16) 5 . . . ?
N4 C10 C11 C12 165.89(15) . . . . ?
C13 N4 C13 C14 -169.9(2) 5 . . . ?
C10 N4 C13 C14 68.81(18) . . . . ?
C10 N4 C13 C14 -48.9(2) 5 . . . ?
N4 C13 C14 C15 -170.47(16) . . . . ?

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_RS131A_0m
_database_code_depnum_ccdc_archive 'CCDC 1984458'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University 
United States of America
;
_audit_update_record             
;
2020-02-15 deposited with the CCDC.	2020-06-01 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         'C6 H3 N3 O6, C12 H28 N, C N S'
_chemical_formula_sum            'C19 H31 N5 O6 S'
_chemical_formula_weight         457.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.2223(10)
_cell_length_b                   12.5540(16)
_cell_length_c                   20.447(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2367.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9828
_cell_measurement_theta_min      2.9162
_cell_measurement_theta_max      33.0726

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.380
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6689
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            38913
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.569
_diffrn_reflns_theta_max         33.129
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8366
_reflns_number_gt                6968
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     0.900
_reflns_Friedel_fraction_full    0.999

_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 v2018.1-0 (Bruker, 2018)'
_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 Rev988 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The isocyanate is disordered over two orientations. The occupancy 
ratio refined to 0.773(5) to 0.227(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)+(0.0425P)²+0.2401P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0106(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2700 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.035(19)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8366
_refine_ls_number_parameters     313
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.003
_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 0.6584(4) 0.5106(3) 0.51529(13) 0.0357(4) Uani 0.773(5) 1 d D . P A 1
C7 C 0.6374(6) 0.5786(3) 0.5846(3) 0.0334(9) Uani 0.773(5) 1 d D . P A 1
N4 N 0.6204(10) 0.6246(7) 0.6322(4) 0.071(4) Uani 0.773(5) 1 d D . P A 1
S1B S 0.6141(7) 0.6225(4) 0.6337(3) 0.0373(11) Uani 0.227(5) 1 d D . P A 2
C7B C 0.632(2) 0.5545(14) 0.5653(9) 0.039(4) Uani 0.227(5) 1 d D . P A 2
N4B N 0.638(4) 0.507(3) 0.5174(14) 0.037(8) Uani 0.227(5) 1 d D . P A 2
O1 O 0.3344(2) 0.80566(11) 0.64168(7) 0.0527(4) Uani 1 1 d . . . . .
O2 O 0.4899(2) 0.91519(10) 0.59892(7) 0.0516(4) Uani 1 1 d . . . . .
O3 O 0.5248(2) 0.91836(13) 0.36222(8) 0.0602(4) Uani 1 1 d . . . . .
O4 O 0.45519(18) 0.77988(12) 0.30718(6) 0.0499(4) Uani 1 1 d . . . . .
O5 O 0.31290(17) 0.46164(10) 0.42436(7) 0.0443(3) Uani 1 1 d . . . . .
O6 O 0.24567(16) 0.47655(10) 0.52549(7) 0.0438(3) Uani 1 1 d . . . . .
N1 N 0.40811(19) 0.83799(12) 0.59631(7) 0.0385(3) Uani 1 1 d . . . . .
N2 N 0.47436(17) 0.82854(13) 0.35835(7) 0.0386(3) Uani 1 1 d . . . . .
N3 N 0.29668(15) 0.51266(11) 0.47511(7) 0.0337(3) Uani 1 1 d . . . . .
N5 N 0.42967(13) 0.25883(9) 0.65540(6) 0.0239(2) Uani 1 1 d . . . . .
C1 C 0.39834(17) 0.78045(12) 0.53367(8) 0.0288(3) Uani 1 1 d . . . . .
C2 C 0.34532(16) 0.67780(12) 0.53426(7) 0.0275(3) Uani 1 1 d . . . . .
H2 H 0.312417 0.645104 0.573447 0.033 Uiso 1 1 calc R U . . .
C3 C 0.34242(16) 0.62492(11) 0.47516(8) 0.0276(3) Uani 1 1 d . . . . .
C4 C 0.38397(17) 0.67118(13) 0.41682(8) 0.0296(3) Uani 1 1 d . . . . .
H4 H 0.379318 0.633407 0.376621 0.036 Uiso 1 1 calc R U . . .
C5 C 0.43278(17) 0.77542(13) 0.41985(8) 0.0291(3) Uani 1 1 d . . . . .
C6 C 0.44406(17) 0.83204(12) 0.47747(8) 0.0298(3) Uani 1 1 d . . . . .
H6 H 0.481194 0.902601 0.478525 0.036 Uiso 1 1 calc R U . . .
C8 C 0.35795(16) 0.36083(11) 0.67868(8) 0.0274(3) Uani 1 1 d . . . . .
H8A H 0.409774 0.421793 0.658753 0.033 Uiso 1 1 calc R U . . .
H8AB H 0.257270 0.362027 0.661896 0.033 Uiso 1 1 calc R U . . .
C9 C 0.3530(2) 0.37784(13) 0.75194(8) 0.0358(3) Uani 1 1 d . . . . .
H9A H 0.452543 0.379078 0.770070 0.043 Uiso 1 1 calc R U . . .
H9AB H 0.298634 0.319325 0.773192 0.043 Uiso 1 1 calc R U . . .
C10 C 0.2779(2) 0.48398(16) 0.76444(10) 0.0477(5) Uani 1 1 d . . . . .
H10A H 0.327466 0.540323 0.739927 0.072 Uiso 1 1 calc R U . . .
H10B H 0.281289 0.500388 0.811276 0.072 Uiso 1 1 calc R U . . .
H10C H 0.176646 0.479524 0.750169 0.072 Uiso 1 1 calc R U . . .
C11 C 0.58332(15) 0.24921(12) 0.68156(7) 0.0267(3) Uani 1 1 d . . . . .
H11A H 0.577847 0.237635 0.729389 0.032 Uiso 1 1 calc R U . . .
H11B H 0.628020 0.184877 0.662125 0.032 Uiso 1 1 calc R U . . .
C12 C 0.68334(17) 0.34300(14) 0.66901(9) 0.0329(3) Uani 1 1 d . . . . .
H12A H 0.646065 0.407094 0.691654 0.040 Uiso 1 1 calc R U . . .
H12B H 0.687556 0.358325 0.621550 0.040 Uiso 1 1 calc R U . . .
C13 C 0.83465(18) 0.31575(17) 0.69437(9) 0.0408(4) Uani 1 1 d . . . . .
H13A H 0.869137 0.250501 0.673149 0.061 Uiso 1 1 calc R U . . .
H13B H 0.830706 0.304840 0.741795 0.061 Uiso 1 1 calc R U . . .
H13C H 0.901188 0.374427 0.684438 0.061 Uiso 1 1 calc R U . . .
C14 C 0.42812(16) 0.26690(12) 0.58105(7) 0.0269(3) Uani 1 1 d . . . . .
H14A H 0.326429 0.276842 0.566788 0.032 Uiso 1 1 calc R U . . .
H14B H 0.482333 0.331752 0.568374 0.032 Uiso 1 1 calc R U . . .
C15 C 0.4907(2) 0.17387(14) 0.54378(8) 0.0389(4) Uani 1 1 d . . . . .
H15A H 0.440814 0.107273 0.556666 0.047 Uiso 1 1 calc R U . . .
H15B H 0.595154 0.166240 0.553900 0.047 Uiso 1 1 calc R U . . .
C16 C 0.4702(2) 0.19375(16) 0.47105(9) 0.0409(4) Uani 1 1 d . . . . .
H16A H 0.508409 0.133084 0.446285 0.061 Uiso 1 1 calc R U . . .
H16B H 0.522303 0.258604 0.458419 0.061 Uiso 1 1 calc R U . . .
H16C H 0.366727 0.202367 0.461537 0.061 Uiso 1 1 calc R U . . .
C17 C 0.35001(16) 0.16001(11) 0.67949(7) 0.0268(3) Uani 1 1 d . . . . .
H17A H 0.406227 0.096488 0.666058 0.032 Uiso 1 1 calc R U . . .
H17B H 0.348715 0.161498 0.727897 0.032 Uiso 1 1 calc R U . . .
C18 C 0.19500(18) 0.14664(14) 0.65546(9) 0.0365(4) Uani 1 1 d . . . . .
H18A H 0.193672 0.142947 0.607101 0.044 Uiso 1 1 calc R U . . .
H18B H 0.135862 0.208523 0.669213 0.044 Uiso 1 1 calc R U . . .
C19 C 0.1318(2) 0.04467(16) 0.68407(11) 0.0450(4) Uani 1 1 d . . . . .
H19A H 0.031950 0.035609 0.668625 0.068 Uiso 1 1 calc R U . . .
H19B H 0.132335 0.049138 0.731924 0.068 Uiso 1 1 calc R U . . .
H19C H 0.190394 -0.016322 0.670079 0.068 Uiso 1 1 calc R 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
S1 C7 1.664(5) . ?
C7 N4 1.144(9) . ?
S1B C7B 1.647(15) . ?
C7B N4B 1.15(2) . ?
O1 N1 1.220(2) . ?
O2 N1 1.229(2) . ?
O3 N2 1.222(2) . ?
O4 N2 1.224(2) . ?
O5 N3 1.2287(19) . ?
O6 N3 1.220(2) . ?
N1 C1 1.473(2) . ?
N2 C5 1.474(2) . ?
N3 C3 1.4710(19) . ?
N5 C8 1.5178(18) . ?
N5 C11 1.5194(18) . ?
N5 C17 1.5236(19) . ?
N5 C14 1.5237(18) . ?
C1 C2 1.378(2) . ?
C1 C6 1.385(2) . ?
C2 C3 1.379(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(2) . ?
C4 C5 1.385(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9500 . ?
C8 C9 1.514(2) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.523(2) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.518(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.527(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.509(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.520(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.521(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.523(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
N4 C7 S1 178.7(6) . . ?
N4B C7B S1B 177(3) . . ?
O1 N1 O2 124.84(15) . . ?
O1 N1 C1 117.65(15) . . ?
O2 N1 C1 117.51(15) . . ?
O3 N2 O4 124.80(16) . . ?
O3 N2 C5 117.45(15) . . ?
O4 N2 C5 117.75(15) . . ?
O6 N3 O5 124.51(14) . . ?
O6 N3 C3 117.78(14) . . ?
O5 N3 C3 117.71(14) . . ?
C8 N5 C11 111.29(11) . . ?
C8 N5 C17 112.05(11) . . ?
C11 N5 C17 105.73(11) . . ?
C8 N5 C14 104.64(11) . . ?
C11 N5 C14 111.42(11) . . ?
C17 N5 C14 111.85(11) . . ?
C2 C1 C6 123.54(14) . . ?
C2 C1 N1 118.19(14) . . ?
C6 C1 N1 118.27(14) . . ?
C1 C2 C3 116.69(14) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
C2 C3 C4 123.30(14) . . ?
C2 C3 N3 117.86(14) . . ?
C4 C3 N3 118.81(14) . . ?
C3 C4 C5 116.68(14) . . ?
C3 C4 H4 121.7 . . ?
C5 C4 H4 121.7 . . ?
C6 C5 C4 123.31(14) . . ?
C6 C5 N2 118.41(14) . . ?
C4 C5 N2 118.28(14) . . ?
C5 C6 C1 116.40(14) . . ?
C5 C6 H6 121.8 . . ?
C1 C6 H6 121.8 . . ?
C9 C8 N5 116.26(12) . . ?
C9 C8 H8A 108.2 . . ?
N5 C8 H8A 108.2 . . ?
C9 C8 H8AB 108.2 . . ?
N5 C8 H8AB 108.2 . . ?
H8A C8 H8AB 107.4 . . ?
C8 C9 C10 107.64(14) . . ?
C8 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
C8 C9 H9AB 110.2 . . ?
C10 C9 H9AB 110.2 . . ?
H9A C9 H9AB 108.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N5 116.46(12) . . ?
C12 C11 H11A 108.2 . . ?
N5 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
N5 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
C11 C12 C13 108.91(14) . . ?
C11 C12 H12A 109.9 . . ?
C13 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
C13 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
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 . . ?
C15 C14 N5 116.67(12) . . ?
C15 C14 H14A 108.1 . . ?
N5 C14 H14A 108.1 . . ?
C15 C14 H14B 108.1 . . ?
N5 C14 H14B 108.1 . . ?
H14A C14 H14B 107.3 . . ?
C14 C15 C16 108.64(14) . . ?
C14 C15 H15A 110.0 . . ?
C16 C15 H15A 110.0 . . ?
C14 C15 H15B 110.0 . . ?
C16 C15 H15B 110.0 . . ?
H15A C15 H15B 108.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N5 116.01(12) . . ?
C18 C17 H17A 108.3 . . ?
N5 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
N5 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C17 C18 C19 109.17(15) . . ?
C17 C18 H18A 109.8 . . ?
C19 C18 H18A 109.8 . . ?
C17 C18 H18B 109.8 . . ?
C19 C18 H18B 109.8 . . ?
H18A C18 H18B 108.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O1 N1 C1 C2 -19.7(2) . . . . ?
O2 N1 C1 C2 160.36(15) . . . . ?
O1 N1 C1 C6 160.80(16) . . . . ?
O2 N1 C1 C6 -19.1(2) . . . . ?
C6 C1 C2 C3 1.6(2) . . . . ?
N1 C1 C2 C3 -177.78(14) . . . . ?
C1 C2 C3 C4 -2.6(2) . . . . ?
C1 C2 C3 N3 175.52(13) . . . . ?
O6 N3 C3 C2 9.5(2) . . . . ?
O5 N3 C3 C2 -170.27(14) . . . . ?
O6 N3 C3 C4 -172.26(15) . . . . ?
O5 N3 C3 C4 7.9(2) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
N3 C3 C4 C5 -176.97(13) . . . . ?
C3 C4 C5 C6 1.5(2) . . . . ?
C3 C4 C5 N2 -178.36(13) . . . . ?
O3 N2 C5 C6 4.1(2) . . . . ?
O4 N2 C5 C6 -175.46(16) . . . . ?
O3 N2 C5 C4 -176.01(17) . . . . ?
O4 N2 C5 C4 4.4(2) . . . . ?
C4 C5 C6 C1 -2.3(2) . . . . ?
N2 C5 C6 C1 177.48(14) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
N1 C1 C6 C5 -179.86(14) . . . . ?
C11 N5 C8 C9 -55.79(17) . . . . ?
C17 N5 C8 C9 62.35(17) . . . . ?
C14 N5 C8 C9 -176.26(13) . . . . ?
N5 C8 C9 C10 179.78(14) . . . . ?
C8 N5 C11 C12 -53.31(17) . . . . ?
C17 N5 C11 C12 -175.20(13) . . . . ?
C14 N5 C11 C12 63.07(17) . . . . ?
N5 C11 C12 C13 -176.04(13) . . . . ?
C8 N5 C14 C15 -178.71(14) . . . . ?
C11 N5 C14 C15 60.92(17) . . . . ?
C17 N5 C14 C15 -57.18(17) . . . . ?
N5 C14 C15 C16 176.31(14) . . . . ?
C8 N5 C17 C18 62.87(17) . . . . ?
C11 N5 C17 C18 -175.73(13) . . . . ?
C14 N5 C17 C18 -54.28(16) . . . . ?
N5 C17 C18 C19 -179.89(14) . . . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.036

