# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_Eisenreich_TSC_4_a
_database_code_depnum_ccdc_archive 'CCDC 2358067'
loop_
_audit_author_name
_audit_author_address
'Burkhard Butschke'
;Albert Ludwigs Universitaet Freiburg
Germany
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V137 by Daniel Kratzert, Freiburg 2024, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C15 H15 N3 O S'
_chemical_formula_moiety         'C15 H15 N3 O S'
_chemical_formula_weight         285.36
_chemical_melting_point          ?
_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                   9.889(8)
_cell_length_b                   23.89(2)
_cell_length_c                   12.335(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.52(2)
_cell_angle_gamma                90
_cell_volume                     2882(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9948
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      29.8315
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'Crystals were obtained at room temperature from a mixture of dichloromethane and ethanol by slow solvent evaporation.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.777
_exptl_crystal_size_mid          0.534
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7051
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.845
_shelx_estimated_absorpt_T_max   0.959
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_detector                 CCD
_diffrn_detector_type            'Bruker APEXII'
_diffrn_detector_area_resol_mean 8.3
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            62376
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_theta_min         1.705
_diffrn_reflns_theta_max         30.041
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8434
_reflns_number_gt                7054
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'Bruker BIS 2018.9.0.3/05-Dec-2018 and APEX5_2023.9-2'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+1.4959P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         8434
_refine_ls_number_parameters     375
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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 0.83810(3) 0.49930(2) 0.65025(3) 0.01550(7) Uani 1 1 d . . . . .
S2 S 0.55076(3) 0.87514(2) 1.09134(3) 0.01511(7) Uani 1 1 d . . . . .
O1 O 0.44241(10) 0.68797(4) 0.81359(8) 0.0208(2) Uani 1 1 d . . . . .
O2 O 0.51691(10) 0.63613(4) 1.31619(8) 0.0230(2) Uani 1 1 d . . . . .
N1 N 0.68926(12) 0.56808(5) 0.50782(9) 0.0168(2) Uani 1 1 d D . . . .
H1N H 0.6676(16) 0.5793(7) 0.4420(11) 0.020 Uiso 1 1 d D U . . .
N2 N 0.82288(11) 0.50461(5) 0.43493(9) 0.0153(2) Uani 1 1 d D . . . .
H2N H 0.8752(15) 0.4758(6) 0.4419(13) 0.018 Uiso 1 1 d D U . . .
N3 N 0.76431(11) 0.52308(5) 0.33271(9) 0.0152(2) Uani 1 1 d D . . . .
N4 N 0.51884(13) 0.78357(5) 0.96535(9) 0.0186(2) Uani 1 1 d D . . . .
H4N H 0.5089(17) 0.7696(7) 0.9019(11) 0.022 Uiso 1 1 d D U . . .
N5 N 0.52852(12) 0.86760(5) 0.87740(9) 0.0170(2) Uani 1 1 d D . . . .
H5N H 0.5443(17) 0.9031(5) 0.8798(13) 0.020 Uiso 1 1 d D U . . .
N6 N 0.51627(11) 0.83910(5) 0.77934(9) 0.0164(2) Uani 1 1 d D . . . .
C1 C 0.77930(13) 0.52605(5) 0.52544(10) 0.0135(2) Uani 1 1 d D . . . .
C2 C 0.62837(13) 0.59602(5) 0.59147(10) 0.0150(2) Uani 1 1 d D . . . .
C3 C 0.49935(14) 0.58048(6) 0.61076(11) 0.0200(3) Uani 1 1 d . . . . .
H3 H 0.455292 0.549223 0.573160 0.024 Uiso 1 1 calc R U . . .
C4 C 0.43335(14) 0.61023(6) 0.68482(11) 0.0194(3) Uani 1 1 d . . . . .
H4 H 0.344031 0.599817 0.696789 0.023 Uiso 1 1 calc R U . . .
C5 C 0.49946(13) 0.65525(5) 0.74098(10) 0.0152(2) Uani 1 1 d . . . . .
C6 C 0.63167(13) 0.66952(6) 0.72504(11) 0.0174(3) Uani 1 1 d . . . . .
H6 H 0.678314 0.699247 0.765933 0.021 Uiso 1 1 calc R U . . .
C7 C 0.69517(13) 0.64035(6) 0.64949(11) 0.0177(3) Uani 1 1 d . . . . .
H7 H 0.784489 0.650679 0.637386 0.021 Uiso 1 1 calc R U . . .
C8 C 0.30540(14) 0.67453(7) 0.82952(13) 0.0257(3) Uani 1 1 d . . . . .
H8A H 0.246470 0.673161 0.758325 0.039 Uiso 1 1 calc R U . . .
H8B H 0.271560 0.703247 0.875505 0.039 Uiso 1 1 calc R U . . .
H8C H 0.304546 0.638018 0.865620 0.039 Uiso 1 1 calc R U . . .
C9 C 0.80078(13) 0.49652(5) 0.25124(10) 0.0150(2) Uani 1 1 d . . . . .
H9 H 0.865092 0.466907 0.265327 0.018 Uiso 1 1 calc R U . . .
C10 C 0.74660(13) 0.51033(5) 0.13727(10) 0.0151(2) Uani 1 1 d . . . . .
C11 C 0.79115(15) 0.47862(6) 0.05433(11) 0.0207(3) Uani 1 1 d . . . . .
H11 H 0.852927 0.448476 0.072806 0.025 Uiso 1 1 calc R U . . .
C12 C 0.74559(17) 0.49090(6) -0.05521(12) 0.0256(3) Uani 1 1 d . . . . .
H12 H 0.776470 0.469200 -0.111255 0.031 Uiso 1 1 calc R U . . .
C13 C 0.65551(16) 0.53461(7) -0.08269(12) 0.0267(3) Uani 1 1 d . . . . .
H13 H 0.625021 0.543171 -0.157533 0.032 Uiso 1 1 calc R U . . .
C14 C 0.60969(16) 0.56597(7) -0.00060(12) 0.0266(3) Uani 1 1 d . . . . .
H14 H 0.547294 0.595860 -0.019563 0.032 Uiso 1 1 calc R U . . .
C15 C 0.65426(14) 0.55401(6) 0.10878(11) 0.0208(3) Uani 1 1 d . . . . .
H15 H 0.621993 0.575532 0.164442 0.025 Uiso 1 1 calc R U . . .
C16 C 0.53269(12) 0.83930(5) 0.97310(10) 0.0136(2) Uani 1 1 d D . . . .
C17 C 0.51696(14) 0.74789(5) 1.05871(10) 0.0158(2) Uani 1 1 d D . . . .
C18 C 0.63837(14) 0.72825(6) 1.11792(12) 0.0206(3) Uani 1 1 d . . . . .
H18 H 0.723610 0.739853 1.098740 0.025 Uiso 1 1 calc R U . . .
C19 C 0.63510(14) 0.69184(6) 1.20470(12) 0.0205(3) Uani 1 1 d . . . . .
H19 H 0.718086 0.679069 1.246023 0.025 Uiso 1 1 calc R U . . .
C20 C 0.51003(14) 0.67386(5) 1.23157(11) 0.0167(2) Uani 1 1 d . . . . .
C21 C 0.38833(14) 0.69380(6) 1.17352(11) 0.0185(3) Uani 1 1 d . . . . .
H21 H 0.302985 0.681995 1.192188 0.022 Uiso 1 1 calc R U . . .
C22 C 0.39303(14) 0.73128(6) 1.08766(11) 0.0175(3) Uani 1 1 d . . . . .
H22 H 0.310289 0.745598 1.048529 0.021 Uiso 1 1 calc R U . . .
C23 C 0.3929(2) 0.60856(10) 1.32923(16) 0.0504(6) Uani 1 1 d . . . . .
H23A H 0.347503 0.595462 1.257694 0.076 Uiso 1 1 calc R U . . .
H23B H 0.332662 0.634710 1.360415 0.076 Uiso 1 1 calc R U . . .
H23C H 0.412916 0.576499 1.378570 0.076 Uiso 1 1 calc R U . . .
C24 C 0.49796(13) 0.87025(6) 0.69365(10) 0.0162(2) Uani 1 1 d . . . . .
H24 H 0.491135 0.909631 0.702092 0.019 Uiso 1 1 calc R U . . .
C25 C 0.48734(13) 0.84661(5) 0.58317(10) 0.0152(2) Uani 1 1 d . . . . .
C26 C 0.50965(14) 0.78969(6) 0.56453(11) 0.0185(3) Uani 1 1 d . . . . .
H26 H 0.530223 0.764732 0.624672 0.022 Uiso 1 1 calc R U . . .
C27 C 0.50159(14) 0.76988(6) 0.45795(12) 0.0213(3) Uani 1 1 d . . . . .
H27 H 0.516543 0.731294 0.445363 0.026 Uiso 1 1 calc R U . . .
C28 C 0.47167(14) 0.80630(6) 0.36920(11) 0.0213(3) Uani 1 1 d . . . . .
H28 H 0.468184 0.792694 0.296473 0.026 Uiso 1 1 calc R U . . .
C29 C 0.44704(14) 0.86241(6) 0.38745(11) 0.0207(3) Uani 1 1 d . . . . .
H29 H 0.425185 0.887177 0.327138 0.025 Uiso 1 1 calc R U . . .
C30 C 0.45434(13) 0.88242(6) 0.49398(11) 0.0178(3) Uani 1 1 d . . . . .
H30 H 0.436684 0.920831 0.506090 0.021 Uiso 1 1 calc R U . . .


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 1.6887(17) . ?
S2 C16 1.6778(17) . ?
O1 C5 1.3715(17) . ?
O1 C8 1.434(2) . ?
O2 C20 1.3732(18) . ?
O2 C23 1.422(2) . ?
N1 C1 1.3381(18) . ?
N1 C2 1.4341(18) . ?
N1 H1N 0.851(12) . ?
N2 C1 1.3554(18) . ?
N2 N3 1.3798(17) . ?
N2 H2N 0.857(12) . ?
N3 C9 1.2845(18) . ?
N4 C16 1.340(2) . ?
N4 C17 1.4350(19) . ?
N4 H4N 0.844(13) . ?
N5 C16 1.3557(18) . ?
N5 N6 1.3776(17) . ?
N5 H5N 0.862(13) . ?
N6 C24 1.2834(19) . ?
C2 C3 1.383(2) . ?
C2 C7 1.389(2) . ?
C3 C4 1.394(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(2) . ?
C6 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.466(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(2) . ?
C10 C15 1.397(2) . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 C22 1.384(2) . ?
C17 C18 1.391(2) . ?
C18 C19 1.383(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.395(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(2) . ?
C21 C22 1.393(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.464(2) . ?
C24 H24 0.9500 . ?
C25 C30 1.394(2) . ?
C25 C26 1.402(2) . ?
C26 C27 1.388(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.395(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.387(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.390(2) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?

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
C5 O1 C8 116.77(11) . . ?
C20 O2 C23 116.32(12) . . ?
C1 N1 C2 124.93(12) . . ?
C1 N1 H1N 117.3(11) . . ?
C2 N1 H1N 117.8(11) . . ?
C1 N2 N3 119.35(12) . . ?
C1 N2 H2N 118.8(10) . . ?
N3 N2 H2N 120.9(10) . . ?
C9 N3 N2 115.36(12) . . ?
C16 N4 C17 123.10(12) . . ?
C16 N4 H4N 117.2(11) . . ?
C17 N4 H4N 119.7(11) . . ?
C16 N5 N6 120.35(12) . . ?
C16 N5 H5N 118.6(11) . . ?
N6 N5 H5N 120.6(11) . . ?
C24 N6 N5 114.83(13) . . ?
N1 C1 N2 115.78(12) . . ?
N1 C1 S1 124.26(10) . . ?
N2 C1 S1 119.95(11) . . ?
C3 C2 C7 119.77(12) . . ?
C3 C2 N1 119.68(12) . . ?
C7 C2 N1 120.47(12) . . ?
C2 C3 C4 120.63(13) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.35(13) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
O1 C5 C4 123.92(12) . . ?
O1 C5 C6 115.98(12) . . ?
C4 C5 C6 120.09(12) . . ?
C7 C6 C5 119.99(12) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.09(13) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C10 122.28(13) . . ?
N3 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C11 C10 C15 119.12(13) . . ?
C11 C10 C9 118.07(13) . . ?
C15 C10 C9 122.81(12) . . ?
C12 C11 C10 120.37(14) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.14(14) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.80(14) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.51(15) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 120.06(13) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
N4 C16 N5 116.34(12) . . ?
N4 C16 S2 124.43(10) . . ?
N5 C16 S2 119.21(11) . . ?
C22 C17 C18 119.74(13) . . ?
C22 C17 N4 119.63(12) . . ?
C18 C17 N4 120.59(12) . . ?
C19 C18 C17 120.07(13) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.04(13) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
O2 C20 C21 123.92(12) . . ?
O2 C20 C19 115.90(12) . . ?
C21 C20 C19 120.18(13) . . ?
C20 C21 C22 119.21(13) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C17 C22 C21 120.72(13) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N6 C24 C25 121.65(13) . . ?
N6 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
C30 C25 C26 119.34(13) . . ?
C30 C25 C24 118.29(13) . . ?
C26 C25 C24 122.37(12) . . ?
C27 C26 C25 119.83(13) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C28 120.41(14) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C29 C28 C27 119.82(13) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C30 120.00(13) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C25 120.56(14) . . ?
C29 C30 H30 119.7 . . ?
C25 C30 H30 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N3 C9 -172.88(12) . . . . ?
C16 N5 N6 C24 172.54(12) . . . . ?
C2 N1 C1 N2 178.81(12) . . . . ?
C2 N1 C1 S1 -0.81(19) . . . . ?
N3 N2 C1 N1 -5.89(17) . . . . ?
N3 N2 C1 S1 173.76(9) . . . . ?
C1 N1 C2 C3 -97.73(17) . . . . ?
C1 N1 C2 C7 85.42(18) . . . . ?
C7 C2 C3 C4 2.5(2) . . . . ?
N1 C2 C3 C4 -174.37(13) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C8 O1 C5 C4 -1.08(19) . . . . ?
C8 O1 C5 C6 178.88(12) . . . . ?
C3 C4 C5 O1 178.47(13) . . . . ?
C3 C4 C5 C6 -1.5(2) . . . . ?
O1 C5 C6 C7 -177.13(12) . . . . ?
C4 C5 C6 C7 2.8(2) . . . . ?
C5 C6 C7 C2 -1.5(2) . . . . ?
C3 C2 C7 C6 -1.2(2) . . . . ?
N1 C2 C7 C6 175.69(12) . . . . ?
N2 N3 C9 C10 179.10(11) . . . . ?
N3 C9 C10 C11 -179.22(13) . . . . ?
N3 C9 C10 C15 1.6(2) . . . . ?
C15 C10 C11 C12 0.9(2) . . . . ?
C9 C10 C11 C12 -178.35(13) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C11 C12 C13 C14 -0.5(2) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C13 C14 C15 C10 0.4(2) . . . . ?
C11 C10 C15 C14 -1.0(2) . . . . ?
C9 C10 C15 C14 178.20(13) . . . . ?
C17 N4 C16 N5 -178.09(12) . . . . ?
C17 N4 C16 S2 0.45(19) . . . . ?
N6 N5 C16 N4 -2.57(18) . . . . ?
N6 N5 C16 S2 178.81(9) . . . . ?
C16 N4 C17 C22 96.42(16) . . . . ?
C16 N4 C17 C18 -85.90(17) . . . . ?
C22 C17 C18 C19 0.6(2) . . . . ?
N4 C17 C18 C19 -177.05(12) . . . . ?
C17 C18 C19 C20 1.3(2) . . . . ?
C23 O2 C20 C21 12.6(2) . . . . ?
C23 O2 C20 C19 -167.05(16) . . . . ?
C18 C19 C20 O2 177.61(13) . . . . ?
C18 C19 C20 C21 -2.0(2) . . . . ?
O2 C20 C21 C22 -178.81(12) . . . . ?
C19 C20 C21 C22 0.8(2) . . . . ?
C18 C17 C22 C21 -1.9(2) . . . . ?
N4 C17 C22 C21 175.83(12) . . . . ?
C20 C21 C22 C17 1.2(2) . . . . ?
N5 N6 C24 C25 178.04(11) . . . . ?
N6 C24 C25 C30 173.89(12) . . . . ?
N6 C24 C25 C26 -6.4(2) . . . . ?
C30 C25 C26 C27 1.4(2) . . . . ?
C24 C25 C26 C27 -178.35(12) . . . . ?
C25 C26 C27 C28 0.1(2) . . . . ?
C26 C27 C28 C29 -1.3(2) . . . . ?
C27 C28 C29 C30 1.0(2) . . . . ?
C28 C29 C30 C25 0.5(2) . . . . ?
C26 C25 C30 C29 -1.7(2) . . . . ?
C24 C25 C30 C29 178.05(12) . . . . ?

####################################################################### 
# 
# 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_Eisenreich_Probe8_Venture_a
_database_code_depnum_ccdc_archive 'CCDC 2358493'
loop_
_audit_author_name
_audit_author_address
'Burkhard Butschke'
;Albert Ludwigs Universitaet Freiburg
Germany
;
_audit_update_record             
;
2024-05-27 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V136 by Daniel Kratzert, Freiburg 2024, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C14 H13 N3 S'
_chemical_formula_moiety         'C14 H13 N3 S'
_chemical_formula_weight         255.33
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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'

_cell_length_a                   5.9879(13)
_cell_length_b                   10.235(3)
_cell_length_c                   11.312(3)
_cell_angle_alpha                66.744(9)
_cell_angle_beta                 82.452(8)
_cell_angle_gamma                86.562(13)
_cell_volume                     631.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      2.166
_cell_measurement_theta_max      30.5625
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'Crystals were obtained at room temperature from a solvent mixture dichloromethane/ethanol (1:2)'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.774
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6811
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.980
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            37702
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_theta_min         1.973
_diffrn_reflns_theta_max         30.588
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3875
_reflns_number_gt                3498
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'Bruker BIS 8.5.0.27 Release/2023-03-20 and APEX5 2023.9-2'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0354P)²+0.2783P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3875
_refine_ls_number_parameters     169
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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 1.01723(4) 0.61083(3) 0.14053(3) 0.01838(7) Uani 1 1 d . . . . .
N1 N 0.59194(15) 0.55479(10) 0.26255(9) 0.01737(17) Uani 1 1 d D . . . .
H1N H 0.467(2) 0.5164(15) 0.2667(14) 0.021 Uiso 1 1 d D U . . .
N2 N 0.71506(15) 0.44427(9) 0.12603(9) 0.01718(17) Uani 1 1 d D . . . .
H2N H 0.812(2) 0.4331(15) 0.0662(13) 0.021 Uiso 1 1 d D U . . .
N3 N 0.51539(14) 0.37101(9) 0.16490(9) 0.01620(16) Uani 1 1 d D . . . .
C1 C 0.77438(18) 0.62341(11) 0.41137(10) 0.01785(19) Uani 1 1 d . . . . .
H1 H 0.900008 0.563695 0.406621 0.021 Uiso 1 1 calc R U . . .
C2 C 0.76659(19) 0.69988(12) 0.48980(10) 0.0206(2) Uani 1 1 d . . . . .
H2 H 0.888164 0.692631 0.538277 0.025 Uiso 1 1 calc R U . . .
C3 C 0.58252(19) 0.78691(12) 0.49798(11) 0.0210(2) Uani 1 1 d . . . . .
H3 H 0.578567 0.838909 0.551663 0.025 Uiso 1 1 calc R U . . .
C4 C 0.40491(19) 0.79729(12) 0.42734(11) 0.0217(2) Uani 1 1 d . . . . .
H4 H 0.278804 0.856401 0.432776 0.026 Uiso 1 1 calc R U . . .
C5 C 0.41100(18) 0.72109(11) 0.34826(11) 0.0192(2) Uani 1 1 d . . . . .
H5 H 0.288880 0.727874 0.300280 0.023 Uiso 1 1 calc R U . . .
C6 C 0.59640(17) 0.63518(10) 0.33992(10) 0.01532(18) Uani 1 1 d D . . . .
C7 C 0.76161(17) 0.53448(10) 0.18065(9) 0.01498(18) Uani 1 1 d D . . . .
C8 C 0.49576(17) 0.28165(11) 0.11284(10) 0.01775(19) Uani 1 1 d . . . . .
H8 H 0.612096 0.275046 0.049645 0.021 Uiso 1 1 calc R U . . .
C9 C 0.29983(17) 0.19019(11) 0.14815(10) 0.01662(18) Uani 1 1 d . . . . .
C10 C 0.11498(18) 0.19872(11) 0.23446(10) 0.0189(2) Uani 1 1 d . . . . .
H10 H 0.111737 0.267965 0.271093 0.023 Uiso 1 1 calc R U . . .
C11 C -0.06362(19) 0.10589(13) 0.26649(11) 0.0233(2) Uani 1 1 d . . . . .
H11 H -0.188846 0.111707 0.325241 0.028 Uiso 1 1 calc R U . . .
C12 C -0.0604(2) 0.00385(12) 0.21283(12) 0.0241(2) Uani 1 1 d . . . . .
H12 H -0.183049 -0.059451 0.235054 0.029 Uiso 1 1 calc R U . . .
C13 C 0.1218(2) -0.00468(12) 0.12736(12) 0.0242(2) Uani 1 1 d . . . . .
H13 H 0.124562 -0.074145 0.091008 0.029 Uiso 1 1 calc R U . . .
C14 C 0.30097(19) 0.08831(12) 0.09451(11) 0.0220(2) Uani 1 1 d . . . . .
H14 H 0.425160 0.082543 0.035126 0.026 Uiso 1 1 calc R U . . .


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 1.6853(11) . ?
N1 C7 1.3466(13) . ?
N1 C6 1.4217(12) . ?
N1 H1N 0.853(11) . ?
N2 C7 1.3559(12) . ?
N2 N3 1.3762(12) . ?
N2 H2N 0.871(11) . ?
N3 C8 1.2860(13) . ?
C1 C2 1.3909(14) . ?
C1 C6 1.3919(14) . ?
C1 H1 0.9500 . ?
C2 C3 1.3919(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.3869(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3959(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.3912(14) . ?
C5 H5 0.9500 . ?
C8 C9 1.4579(14) . ?
C8 H8 0.9500 . ?
C9 C14 1.3976(14) . ?
C9 C10 1.3992(15) . ?
C10 C11 1.3878(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.3980(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3821(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3906(16) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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
C7 N1 C6 127.46(9) . . ?
C7 N1 H1N 115.8(9) . . ?
C6 N1 H1N 116.7(9) . . ?
C7 N2 N3 120.11(9) . . ?
C7 N2 H2N 119.6(9) . . ?
N3 N2 H2N 120.3(9) . . ?
C8 N3 N2 114.70(9) . . ?
C2 C1 C6 119.39(10) . . ?
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
C1 C2 C3 120.69(10) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.63(10) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.17(10) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.81(10) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 120.31(9) . . ?
C5 C6 N1 118.05(9) . . ?
C1 C6 N1 121.55(9) . . ?
N1 C7 N2 114.89(9) . . ?
N1 C7 S1 126.38(8) . . ?
N2 C7 S1 118.73(8) . . ?
N3 C8 C9 121.79(9) . . ?
N3 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C14 C9 C10 119.25(10) . . ?
C14 C9 C8 117.86(9) . . ?
C10 C9 C8 122.88(9) . . ?
C11 C10 C9 119.91(10) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.41(11) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 119.82(10) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.07(10) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.53(11) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 N3 C8 -175.61(9) . . . . ?
C6 C1 C2 C3 0.42(16) . . . . ?
C1 C2 C3 C4 0.10(17) . . . . ?
C2 C3 C4 C5 -0.13(17) . . . . ?
C3 C4 C5 C6 -0.34(17) . . . . ?
C4 C5 C6 C1 0.86(16) . . . . ?
C4 C5 C6 N1 177.44(10) . . . . ?
C2 C1 C6 C5 -0.90(16) . . . . ?
C2 C1 C6 N1 -177.35(10) . . . . ?
C7 N1 C6 C5 138.09(11) . . . . ?
C7 N1 C6 C1 -45.38(16) . . . . ?
C6 N1 C7 N2 175.47(9) . . . . ?
C6 N1 C7 S1 -5.27(16) . . . . ?
N3 N2 C7 N1 -6.19(14) . . . . ?
N3 N2 C7 S1 174.49(7) . . . . ?
N2 N3 C8 C9 176.88(9) . . . . ?
N3 C8 C9 C14 -174.92(10) . . . . ?
N3 C8 C9 C10 3.87(16) . . . . ?
C14 C9 C10 C11 0.45(16) . . . . ?
C8 C9 C10 C11 -178.33(10) . . . . ?
C9 C10 C11 C12 -0.12(17) . . . . ?
C10 C11 C12 C13 0.00(17) . . . . ?
C11 C12 C13 C14 -0.22(17) . . . . ?
C12 C13 C14 C9 0.55(17) . . . . ?
C10 C9 C14 C13 -0.66(16) . . . . ?
C8 C9 C14 C13 178.17(10) . . . . ?

####################################################################### 
# 
# 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_Eisenreich_TSC_13_a
_database_code_depnum_ccdc_archive 'CCDC 2358068'
loop_
_audit_author_name
_audit_author_address
'Burkhard Butschke'
;Albert Ludwigs Universitaet Freiburg
Germany
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V137 by Daniel Kratzert, Freiburg 2024, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C14 H11 Cl2 N3 S'
_chemical_formula_moiety         'C14 H11 Cl2 N3 S'
_chemical_formula_weight         324.22
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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'

_cell_length_a                   7.866(2)
_cell_length_b                   8.231(2)
_cell_length_c                   11.963(5)
_cell_angle_alpha                92.336(4)
_cell_angle_beta                 96.812(11)
_cell_angle_gamma                111.933(13)
_cell_volume                     710.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      2.679
_cell_measurement_theta_max      31.4645
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'Crystals were obtained at room temperature from a mixture of dichloromethane and ethanol by slow solvent evaporation.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_min          0.162
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6913
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.778
_shelx_estimated_absorpt_T_max   0.910
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_detector                 CCD
_diffrn_detector_type            'Bruker APEXII'
_diffrn_detector_area_resol_mean 8.3
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            33050
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_theta_min         1.722
_diffrn_reflns_theta_max         31.518
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4732
_reflns_number_gt                4300
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'Bruker BIS 2018.9.0.3/05-Dec-2018 and APEX5_2023.9-2'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0301P)²+0.3561P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4732
_refine_ls_number_parameters     187
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0683
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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
Cl1 Cl 0.25214(4) 0.72448(3) 0.97677(2) 0.02021(6) Uani 1 1 d . . . . .
Cl2 Cl 0.15773(4) 0.04931(3) 0.84415(2) 0.01577(6) Uani 1 1 d . . . . .
S1 S 0.11921(4) 0.37352(3) 0.38691(2) 0.01488(6) Uani 1 1 d . . . . .
N1 N 0.29239(13) 0.22829(12) 0.53363(7) 0.01432(16) Uani 1 1 d D . . . .
H1N H 0.330(2) 0.2217(19) 0.6019(10) 0.017 Uiso 1 1 d D U . . .
N2 N 0.15462(12) 0.39912(11) 0.60947(7) 0.01301(15) Uani 1 1 d D . . . .
H2N H 0.0860(19) 0.4601(18) 0.6031(11) 0.016 Uiso 1 1 d D U . . .
N3 N 0.21467(12) 0.36154(11) 0.71403(7) 0.01240(15) Uani 1 1 d D . . . .
C1 C 0.19318(14) 0.32886(12) 0.51586(8) 0.01191(16) Uani 1 1 d D . . . .
C2 C 0.34809(14) 0.14477(13) 0.44565(8) 0.01229(17) Uani 1 1 d D . . . .
C3 C 0.21530(14) 0.01006(13) 0.37179(9) 0.01448(18) Uani 1 1 d . . . . .
H3 H 0.087742 -0.026001 0.379019 0.017 Uiso 1 1 calc R U . . .
C4 C 0.27137(15) -0.07121(14) 0.28726(9) 0.01579(18) Uani 1 1 d . . . . .
H4 H 0.181620 -0.162901 0.236253 0.019 Uiso 1 1 calc R U . . .
C5 C 0.45842(15) -0.01877(14) 0.27708(9) 0.01593(18) Uani 1 1 d . . . . .
H5 H 0.495886 -0.073811 0.218708 0.019 Uiso 1 1 calc R U . . .
C6 C 0.59050(14) 0.11416(14) 0.35232(9) 0.01613(18) Uani 1 1 d . . . . .
H6 H 0.718205 0.148789 0.345891 0.019 Uiso 1 1 calc R U . . .
C7 C 0.53544(14) 0.19679(13) 0.43737(8) 0.01440(18) Uani 1 1 d . . . . .
H7 H 0.625141 0.287562 0.488981 0.017 Uiso 1 1 calc R U . . .
C8 C 0.16914(14) 0.42834(13) 0.79885(8) 0.01288(17) Uani 1 1 d . . . . .
H8 H 0.102044 0.502527 0.786637 0.015 Uiso 1 1 calc R U . . .
C9 C 0.21949(13) 0.39151(13) 0.91462(8) 0.01169(16) Uani 1 1 d . . . . .
C10 C 0.26073(15) 0.52148(13) 1.00494(8) 0.01404(17) Uani 1 1 d . . . . .
C11 C 0.30946(16) 0.49591(15) 1.11618(9) 0.01756(19) Uani 1 1 d . . . . .
H11 H 0.337183 0.587193 1.174822 0.021 Uiso 1 1 calc R U . . .
C12 C 0.31722(16) 0.33515(15) 1.14072(9) 0.0183(2) Uani 1 1 d . . . . .
H12 H 0.352458 0.316646 1.216380 0.022 Uiso 1 1 calc R U . . .
C13 C 0.27354(15) 0.20154(14) 1.05485(9) 0.01611(18) Uani 1 1 d . . . . .
H13 H 0.277319 0.091077 1.071836 0.019 Uiso 1 1 calc R U . . .
C14 C 0.22430(14) 0.22937(13) 0.94403(8) 0.01236(17) Uani 1 1 d . . . . .


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
Cl1 C10 1.7420(11) . ?
Cl2 C14 1.7394(11) . ?
S1 C1 1.6871(11) . ?
N1 C1 1.3405(13) . ?
N1 C2 1.4310(13) . ?
N1 H1N 0.845(12) . ?
N2 C1 1.3562(13) . ?
N2 N3 1.3725(12) . ?
N2 H2N 0.863(11) . ?
N3 C8 1.2837(13) . ?
C2 C7 1.3899(15) . ?
C2 C3 1.3918(14) . ?
C3 C4 1.3913(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.3923(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3912(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.3976(15) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.4699(14) . ?
C8 H8 0.9500 . ?
C9 C14 1.4068(14) . ?
C9 C10 1.4073(14) . ?
C10 C11 1.3871(15) . ?
C11 C12 1.3886(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3872(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.3890(15) . ?
C13 H13 0.9500 . ?

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 N1 C2 124.26(8) . . ?
C1 N1 H1N 116.2(10) . . ?
C2 N1 H1N 119.4(10) . . ?
C1 N2 N3 119.21(8) . . ?
C1 N2 H2N 120.3(9) . . ?
N3 N2 H2N 120.3(9) . . ?
C8 N3 N2 116.00(9) . . ?
N1 C1 N2 116.21(9) . . ?
N1 C1 S1 124.20(8) . . ?
N2 C1 S1 119.59(8) . . ?
C7 C2 C3 121.00(9) . . ?
C7 C2 N1 119.15(9) . . ?
C3 C2 N1 119.83(9) . . ?
C4 C3 C2 119.28(10) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.30(10) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.06(9) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.04(10) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 119.31(9) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
N3 C8 C9 120.85(9) . . ?
N3 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C14 C9 C10 115.86(9) . . ?
C14 C9 C8 124.31(9) . . ?
C10 C9 C8 119.80(9) . . ?
C11 C10 C9 122.90(10) . . ?
C11 C10 Cl1 118.10(8) . . ?
C9 C10 Cl1 119.00(8) . . ?
C10 C11 C12 119.14(10) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 120.06(10) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 119.96(10) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 122.03(9) . . ?
C13 C14 Cl2 116.33(8) . . ?
C9 C14 Cl2 121.57(8) . . ?

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
C1 N2 N3 C8 -178.16(9) . . . . ?
C2 N1 C1 N2 -179.30(9) . . . . ?
C2 N1 C1 S1 -0.29(15) . . . . ?
N3 N2 C1 N1 -1.20(14) . . . . ?
N3 N2 C1 S1 179.74(7) . . . . ?
C1 N1 C2 C7 114.59(12) . . . . ?
C1 N1 C2 C3 -67.14(14) . . . . ?
C7 C2 C3 C4 -1.16(15) . . . . ?
N1 C2 C3 C4 -179.40(9) . . . . ?
C2 C3 C4 C5 0.29(15) . . . . ?
C3 C4 C5 C6 0.68(16) . . . . ?
C4 C5 C6 C7 -0.81(16) . . . . ?
C3 C2 C7 C6 1.04(15) . . . . ?
N1 C2 C7 C6 179.29(9) . . . . ?
C5 C6 C7 C2 -0.05(15) . . . . ?
N2 N3 C8 C9 177.62(9) . . . . ?
N3 C8 C9 C14 -35.65(15) . . . . ?
N3 C8 C9 C10 146.54(10) . . . . ?
C14 C9 C10 C11 2.10(15) . . . . ?
C8 C9 C10 C11 -179.92(10) . . . . ?
C14 C9 C10 Cl1 -178.34(7) . . . . ?
C8 C9 C10 Cl1 -0.35(13) . . . . ?
C9 C10 C11 C12 -0.44(17) . . . . ?
Cl1 C10 C11 C12 179.99(9) . . . . ?
C10 C11 C12 C13 -1.07(17) . . . . ?
C11 C12 C13 C14 0.82(17) . . . . ?
C12 C13 C14 C9 0.97(16) . . . . ?
C12 C13 C14 Cl2 -175.99(8) . . . . ?
C10 C9 C14 C13 -2.35(15) . . . . ?
C8 C9 C14 C13 179.76(10) . . . . ?
C10 C9 C14 Cl2 174.46(7) . . . . ?
C8 C9 C14 Cl2 -3.43(14) . . . . ?

####################################################################### 
# 
# 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_Eisenreich_TSC_22_a
_database_code_depnum_ccdc_archive 'CCDC 2358072'
loop_
_audit_author_name
_audit_author_address
'Burkhard Butschke'
;Albert Ludwigs Universitaet Freiburg
Germany
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V137 by Daniel Kratzert, Freiburg 2024, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C14 H14 N4 O S'
_chemical_formula_moiety         'C14 H14 N4 O S'
_chemical_formula_weight         286.35
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_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                   6.643(6)
_cell_length_b                   7.435(7)
_cell_length_c                   28.49(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1407(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8722
_cell_measurement_theta_min      2.8315
_cell_measurement_theta_max      31.488
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_recrystallization_method 
'Crystals were obtained at room temperature from ethanol by slow solvent evaporation.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.953
_exptl_crystal_size_mid          0.338
_exptl_crystal_size_min          0.297
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6794
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.935
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_detector                 CCD
_diffrn_detector_type            'Bruker APEXII'
_diffrn_detector_area_resol_mean 8.3
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            30967
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_theta_min         1.429
_diffrn_reflns_theta_max         31.578
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4712
_reflns_number_gt                4508
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'Bruker BIS 2018.9.0.3/05-Dec-2018 and APEX5_2023.9-2'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+0.2952P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4712
_refine_ls_number_parameters     188
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1815 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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_
_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 0.22422(6) 0.71825(5) 0.38982(2) 0.01865(9) Uani 1 1 d . . . . .
O1 O 0.88045(18) 0.55575(17) 0.48490(4) 0.0200(2) Uani 1 1 d . . . . .
N1 N 0.1502(2) 0.44967(19) 0.32720(5) 0.0171(3) Uani 1 1 d D . . . .
H1N H 0.198(3) 0.352(2) 0.3151(7) 0.020 Uiso 1 1 d D U . . .
N2 N 0.4180(2) 0.41896(18) 0.37626(5) 0.0157(3) Uani 1 1 d D . . . .
H2N H 0.499(3) 0.458(3) 0.3979(7) 0.019 Uiso 1 1 d D U . . .
N3 N 0.4614(2) 0.26273(19) 0.35347(5) 0.0212(3) Uani 1 1 d D . . . .
N4 N 0.7558(2) 0.37305(17) 0.42619(5) 0.0159(2) Uani 1 1 d . . . . .
C1 C 0.2586(2) 0.52078(19) 0.36254(5) 0.0143(3) Uani 1 1 d D . . . .
C2 C -0.0256(2) 0.5135(2) 0.30449(6) 0.0153(3) Uani 1 1 d D . . . .
C3 C -0.1692(2) 0.6217(2) 0.32640(6) 0.0169(3) Uani 1 1 d . . . . .
H3 H -0.149857 0.660775 0.357820 0.020 Uiso 1 1 calc R U . . .
C4 C -0.3411(2) 0.6717(2) 0.30174(6) 0.0184(3) Uani 1 1 d . . . . .
H4 H -0.438544 0.746065 0.316544 0.022 Uiso 1 1 calc R U . . .
C5 C -0.3729(2) 0.6150(2) 0.25582(6) 0.0198(3) Uani 1 1 d . . . . .
H5 H -0.490903 0.650130 0.239382 0.024 Uiso 1 1 calc R U . . .
C6 C -0.2299(3) 0.5062(2) 0.23425(6) 0.0206(3) Uani 1 1 d . . . . .
H6 H -0.250406 0.466486 0.202922 0.025 Uiso 1 1 calc R U . . .
C7 C -0.0571(3) 0.4553(2) 0.25833(6) 0.0179(3) Uani 1 1 d . . . . .
H7 H 0.040013 0.380902 0.243419 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6245(3) 0.1788(2) 0.36456(7) 0.0233(4) Uani 1 1 d . . . . .
H8 H 0.647724 0.070938 0.347533 0.028 Uiso 1 1 calc R U . . .
C9 C 0.7798(2) 0.2232(2) 0.39920(6) 0.0183(3) Uani 1 1 d . . . . .
C10 C 0.9469(3) 0.1122(2) 0.40279(6) 0.0229(3) Uani 1 1 d . . . . .
H10 H 0.959560 0.008671 0.383473 0.027 Uiso 1 1 calc R U . . .
C11 C 1.0963(3) 0.1560(3) 0.43546(7) 0.0232(3) Uani 1 1 d . . . . .
H11 H 1.212451 0.082407 0.438581 0.028 Uiso 1 1 calc R U . . .
C12 C 1.0734(3) 0.3067(2) 0.46308(6) 0.0205(3) Uani 1 1 d . . . . .
H12 H 1.172457 0.339148 0.485584 0.025 Uiso 1 1 calc R U . . .
C13 C 0.8991(2) 0.4110(2) 0.45694(5) 0.0164(3) Uani 1 1 d . . . . .
C14 C 0.7112(3) 0.6720(2) 0.47682(6) 0.0230(3) Uani 1 1 d . . . . .
H14A H 0.721477 0.724982 0.445414 0.035 Uiso 1 1 calc R U . . .
H14B H 0.710287 0.768039 0.500387 0.035 Uiso 1 1 calc R U . . .
H14C H 0.586344 0.602372 0.479156 0.035 Uiso 1 1 calc R U . . .


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 1.6769(19) . ?
O1 C13 1.345(2) . ?
O1 C14 1.437(2) . ?
N1 C1 1.346(2) . ?
N1 C2 1.417(2) . ?
N1 H1N 0.863(17) . ?
N2 C1 1.359(2) . ?
N2 N3 1.362(2) . ?
N2 H2N 0.868(16) . ?
N3 C8 1.290(2) . ?
N4 C13 1.324(2) . ?
N4 C9 1.363(2) . ?
C2 C3 1.395(2) . ?
C2 C7 1.400(3) . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.465(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(2) . ?
C10 C11 1.399(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.404(2) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C13 O1 C14 117.32(13) . . ?
C1 N1 C2 130.60(14) . . ?
C1 N1 H1N 115.7(14) . . ?
C2 N1 H1N 113.6(14) . . ?
C1 N2 N3 120.18(14) . . ?
C1 N2 H2N 120.3(14) . . ?
N3 N2 H2N 119.3(14) . . ?
C8 N3 N2 118.26(15) . . ?
C13 N4 C9 117.57(14) . . ?
N1 C1 N2 114.40(14) . . ?
N1 C1 S1 128.17(13) . . ?
N2 C1 S1 117.41(12) . . ?
C3 C2 C7 119.74(15) . . ?
C3 C2 N1 123.54(15) . . ?
C7 C2 N1 116.65(14) . . ?
C4 C3 C2 119.31(16) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 121.23(16) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.24(16) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 120.29(16) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 120.19(15) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
N3 C8 C9 130.36(16) . . ?
N3 C8 H8 114.8 . . ?
C9 C8 H8 114.8 . . ?
N4 C9 C10 122.60(16) . . ?
N4 C9 C8 118.78(15) . . ?
C10 C9 C8 118.61(16) . . ?
C9 C10 C11 118.57(17) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 119.38(16) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 117.97(16) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
N4 C13 O1 119.73(15) . . ?
N4 C13 C12 123.90(16) . . ?
O1 C13 C12 116.37(15) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C1 N2 N3 C8 173.50(16) . . . . ?
C2 N1 C1 N2 178.58(15) . . . . ?
C2 N1 C1 S1 -3.3(3) . . . . ?
N3 N2 C1 N1 2.5(2) . . . . ?
N3 N2 C1 S1 -175.84(12) . . . . ?
C1 N1 C2 C3 -28.7(3) . . . . ?
C1 N1 C2 C7 154.40(17) . . . . ?
C7 C2 C3 C4 -0.7(2) . . . . ?
N1 C2 C3 C4 -177.44(15) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C2 -0.1(3) . . . . ?
C3 C2 C7 C6 0.5(2) . . . . ?
N1 C2 C7 C6 177.49(15) . . . . ?
N2 N3 C8 C9 0.2(3) . . . . ?
C13 N4 C9 C10 -0.3(2) . . . . ?
C13 N4 C9 C8 -179.44(15) . . . . ?
N3 C8 C9 N4 1.9(3) . . . . ?
N3 C8 C9 C10 -177.3(2) . . . . ?
N4 C9 C10 C11 0.1(3) . . . . ?
C8 C9 C10 C11 179.20(17) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C9 N4 C13 O1 -178.90(14) . . . . ?
C9 N4 C13 C12 0.3(2) . . . . ?
C14 O1 C13 N4 -5.4(2) . . . . ?
C14 O1 C13 C12 175.36(15) . . . . ?
C11 C12 C13 N4 -0.1(2) . . . . ?
C11 C12 C13 O1 179.16(15) . . . . ?

####################################################################### 
# 
# 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_Eisenreich_TSC_19_a
_database_code_depnum_ccdc_archive 'CCDC 2358070'
loop_
_audit_author_name
_audit_author_address
'Burkhard Butschke'
;Albert Ludwigs Universitaet Freiburg
Germany
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V137 by Daniel Kratzert, Freiburg 2024, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C12 H11 N3 S2'
_chemical_formula_moiety         'C12 H11 N3 S2'
_chemical_formula_weight         261.36
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_vrf_PLAT230_Eisenreich_TSC_19_a 
;PROBLEM: Hirshfeld Test Diff for    S1       --C1       .        8.0 s.u.  
RESPONSE: The resaon for the Hirshfeld-Test Difference for S1 and C1 might be 
due to the special bonding situation. The assignment, however, is unequivocal.
;
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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'

_cell_length_a                   5.689(2)
_cell_length_b                   10.012(3)
_cell_length_c                   11.393(4)
_cell_angle_alpha                71.163(6)
_cell_angle_beta                 82.543(10)
_cell_angle_gamma                87.953(18)
_cell_volume                     609.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      31.511
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'Crystals were obtained at room temperature from a mixture of dichloromethane and ethanol by slow solvent evaporation.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.709
_exptl_crystal_size_mid          0.531
_exptl_crystal_size_min          0.235
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6912
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.757
_shelx_estimated_absorpt_T_max   0.909
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_detector                 CCD
_diffrn_detector_type            'Bruker APEXII'
_diffrn_detector_area_resol_mean 8.3
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            30288
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_theta_min         1.903
_diffrn_reflns_theta_max         31.556
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4060
_reflns_number_gt                3731
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'Bruker BIS 2018.9.0.3/05-Dec-2018 and APEX5_2023.9-2'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;For the disorder model of the 2-thiophenyl moiety, it was necessary to apply 
EADP and EXYZ on C1_1 and C1_2 in order to end up with a stable model without 
NPDs.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²+0.1792P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4060
_refine_ls_number_parameters     197
_refine_ls_number_restraints     208
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0762
_refine_ls_wR_factor_gt          0.0744
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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 0.00026(4) 0.38203(2) 0.86612(2) 0.01658(6) Uani 1 1 d . . . . .
N1 N 0.44294(13) 0.44371(8) 0.74573(7) 0.01633(14) Uani 1 1 d D . . . .
H1N H 0.575(2) 0.4844(13) 0.7404(12) 0.020 Uiso 1 1 d D U . . .
N2 N 0.31140(14) 0.56179(8) 0.88187(7) 0.01567(14) Uani 1 1 d D . . . .
H2N H 0.207(2) 0.5746(13) 0.9404(11) 0.019 Uiso 1 1 d D U . . .
N3 N 0.51308(13) 0.64334(8) 0.83889(7) 0.01488(14) Uani 1 1 d D . . . .
C1 C 0.26501(15) 0.46580(8) 0.82699(8) 0.01354(14) Uani 1 1 d D . . . .
C2 C 0.43506(15) 0.36317(9) 0.66382(8) 0.01437(15) Uani 1 1 d D . . . .
C3 C 0.25413(16) 0.38094(9) 0.58855(8) 0.01651(16) Uani 1 1 d . . . . .
H3 H 0.126170 0.442678 0.595451 0.020 Uiso 1 1 calc R U . . .
C4 C 0.26270(17) 0.30746(10) 0.50326(8) 0.01887(17) Uani 1 1 d . . . . .
H4 H 0.138926 0.318514 0.452425 0.023 Uiso 1 1 calc R U . . .
C5 C 0.45075(17) 0.21788(10) 0.49162(9) 0.02009(17) Uani 1 1 d . . . . .
H5 H 0.455895 0.168549 0.432742 0.024 Uiso 1 1 calc R U . . .
C6 C 0.63124(17) 0.20101(10) 0.56676(9) 0.02079(17) Uani 1 1 d . . . . .
H6 H 0.759994 0.140044 0.559139 0.025 Uiso 1 1 calc R U . . .
C7 C 0.62344(16) 0.27342(10) 0.65320(9) 0.01856(16) Uani 1 1 d . . . . .
H7 H 0.746316 0.261538 0.704693 0.022 Uiso 1 1 calc R U . . .
C8 C 0.53626(16) 0.73993(9) 0.88876(8) 0.01678(16) Uani 1 1 d . . . . .
H8 H 0.419760 0.749520 0.953221 0.020 Uiso 1 1 calc R U . A 1
S1_1 S 0.95951(10) 0.82150(7) 0.73301(5) 0.01984(11) Uani 0.8314(17) 1 d . U P
B 1
C1_1 C 0.73907(16) 0.83368(9) 0.84683(8) 0.01618(15) Uani 0.8314(17) 1 d . U P
B 1
C2_1 C 0.7910(9) 0.9417(4) 0.8919(6) 0.0253(7) Uani 0.8314(17) 1 d . U P B 1
H2_1 H 0.692260 0.963742 0.956966 0.030 Uiso 0.8314(17) 1 calc R U P B 1
C3_1 C 1.0023(6) 1.0153(3) 0.8326(2) 0.0234(4) Uani 0.8314(17) 1 d . U P B 1
H3_1 H 1.060160 1.093234 0.850910 0.028 Uiso 0.8314(17) 1 calc R U P B 1
C4_1 C 1.1134(5) 0.9601(2) 0.7452(3) 0.0227(4) Uani 0.8314(17) 1 d . U P B 1
H4_1 H 1.260247 0.994640 0.696382 0.027 Uiso 0.8314(17) 1 calc R U P B 1
S1_2 S 0.7635(10) 0.9678(5) 0.8972(6) 0.0214(7) Uani 0.1686(17) 1 d . U P B 2
C1_2 C 0.73907(16) 0.83368(9) 0.84683(8) 0.01618(15) Uani 0.1686(17) 1 d . U P
B 2
C2_2 C 0.928(2) 0.8242(17) 0.7594(12) 0.0224(16) Uani 0.1686(17) 1 d . U P B 2
H2_2 H 0.940128 0.753949 0.719357 0.027 Uiso 0.1686(17) 1 calc R U P B 2
C3_2 C 1.099(2) 0.9316(13) 0.7370(15) 0.0200(16) Uani 0.1686(17) 1 d . U P B 2
H3_2 H 1.241082 0.943687 0.680251 0.024 Uiso 0.1686(17) 1 calc R U P B 2
C4_2 C 1.034(3) 1.0109(17) 0.8055(12) 0.0201(16) Uani 0.1686(17) 1 d . U P B 2
H4_2 H 1.128700 1.087364 0.805357 0.024 Uiso 0.1686(17) 1 calc R U P B 2


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 1.6868(10) . ?
N1 C1 1.3431(11) . ?
N1 C2 1.4221(11) . ?
N1 H1N 0.855(11) . ?
N2 C1 1.3539(11) . ?
N2 N3 1.3732(11) . ?
N2 H2N 0.871(11) . ?
N3 C8 1.2879(12) . ?
C2 C7 1.3922(13) . ?
C2 C3 1.3944(13) . ?
C3 C4 1.3909(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.3921(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.3922(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.3945(13) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C1_2 1.4440(13) . ?
C8 C1_1 1.4440(13) . ?
C8 H8 0.9500 . ?
S1_1 C1_1 1.7142(11) . ?
S1_1 C4_1 1.719(2) . ?
C1_1 C2_1 1.394(4) . ?
C2_1 C3_1 1.405(6) . ?
C2_1 H2_1 0.9500 . ?
C3_1 C4_1 1.365(3) . ?
C3_1 H3_1 0.9500 . ?
C4_1 H4_1 0.9500 . ?
S1_2 C1_2 1.638(5) . ?
S1_2 C4_2 1.729(15) . ?
C1_2 C2_2 1.389(12) . ?
C2_2 C3_2 1.418(18) . ?
C2_2 H2_2 0.9500 . ?
C3_2 C4_2 1.297(13) . ?
C3_2 H3_2 0.9500 . ?
C4_2 H4_2 0.9500 . ?

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 N1 C2 127.35(8) . . ?
C1 N1 H1N 117.0(8) . . ?
C2 N1 H1N 115.6(8) . . ?
C1 N2 N3 119.57(7) . . ?
C1 N2 H2N 119.1(8) . . ?
N3 N2 H2N 121.2(8) . . ?
C8 N3 N2 116.14(8) . . ?
N1 C1 N2 115.16(8) . . ?
N1 C1 S1 125.38(7) . . ?
N2 C1 S1 119.44(7) . . ?
C7 C2 C3 120.34(8) . . ?
C7 C2 N1 118.12(8) . . ?
C3 C2 N1 121.35(8) . . ?
C4 C3 C2 119.39(8) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.69(8) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 119.61(8) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 120.15(9) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 119.82(8) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
N3 C8 C1_2 120.09(8) . . ?
N3 C8 C1_1 120.09(8) . . ?
N3 C8 H8 120.0 . . ?
C1_1 C8 H8 120.0 . . ?
C1_1 S1_1 C4_1 91.86(12) . . ?
C2_1 C1_1 C8 127.1(2) . . ?
C2_1 C1_1 S1_1 110.1(2) . . ?
C8 C1_1 S1_1 122.86(7) . . ?
C1_1 C2_1 C3_1 114.1(3) . . ?
C1_1 C2_1 H2_1 123.0 . . ?
C3_1 C2_1 H2_1 123.0 . . ?
C4_1 C3_1 C2_1 111.2(3) . . ?
C4_1 C3_1 H3_1 124.4 . . ?
C2_1 C3_1 H3_1 124.4 . . ?
C3_1 C4_1 S1_1 112.8(2) . . ?
C3_1 C4_1 H4_1 123.6 . . ?
S1_1 C4_1 H4_1 123.6 . . ?
C1_2 S1_2 C4_2 89.9(6) . . ?
C2_2 C1_2 C8 125.1(7) . . ?
C2_2 C1_2 S1_2 112.9(7) . . ?
C8 C1_2 S1_2 121.9(2) . . ?
C1_2 C2_2 C3_2 112.0(12) . . ?
C1_2 C2_2 H2_2 124.0 . . ?
C3_2 C2_2 H2_2 124.0 . . ?
C4_2 C3_2 C2_2 109.8(14) . . ?
C4_2 C3_2 H3_2 125.1 . . ?
C2_2 C3_2 H3_2 125.1 . . ?
C3_2 C4_2 S1_2 115.3(13) . . ?
C3_2 C4_2 H4_2 122.3 . . ?
S1_2 C4_2 H4_2 122.3 . . ?

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
C1 N2 N3 C8 174.66(8) . . . . ?
C2 N1 C1 N2 -171.63(8) . . . . ?
C2 N1 C1 S1 9.88(13) . . . . ?
N3 N2 C1 N1 9.87(12) . . . . ?
N3 N2 C1 S1 -171.55(6) . . . . ?
C1 N1 C2 C7 -136.60(10) . . . . ?
C1 N1 C2 C3 48.36(13) . . . . ?
C7 C2 C3 C4 0.42(13) . . . . ?
N1 C2 C3 C4 175.34(8) . . . . ?
C2 C3 C4 C5 -0.66(14) . . . . ?
C3 C4 C5 C6 0.43(14) . . . . ?
C4 C5 C6 C7 0.03(15) . . . . ?
C3 C2 C7 C6 0.05(14) . . . . ?
N1 C2 C7 C6 -175.04(8) . . . . ?
C5 C6 C7 C2 -0.27(14) . . . . ?
N2 N3 C8 C1_2 -178.12(8) . . . . ?
N2 N3 C8 C1_1 -178.12(8) . . . . ?
N3 C8 C1_1 C2_1 -179.2(3) . . . . ?
N3 C8 C1_1 S1_1 -1.15(13) . . . . ?
C4_1 S1_1 C1_1 C2_1 -0.8(3) . . . . ?
C4_1 S1_1 C1_1 C8 -179.17(12) . . . . ?
C8 C1_1 C2_1 C3_1 179.9(2) . . . . ?
S1_1 C1_1 C2_1 C3_1 1.6(4) . . . . ?
C1_1 C2_1 C3_1 C4_1 -1.8(5) . . . . ?
C2_1 C3_1 C4_1 S1_1 1.1(4) . . . . ?
C1_1 S1_1 C4_1 C3_1 -0.2(2) . . . . ?
N3 C8 C1_2 C2_2 -4.4(8) . . . . ?
N3 C8 C1_2 S1_2 173.8(3) . . . . ?
C4_2 S1_2 C1_2 C2_2 -2.0(9) . . . . ?
C4_2 S1_2 C1_2 C8 179.7(6) . . . . ?
C8 C1_2 C2_2 C3_2 179.7(8) . . . . ?
S1_2 C1_2 C2_2 C3_2 1.4(14) . . . . ?
C1_2 C2_2 C3_2 C4_2 0.3(18) . . . . ?
C2_2 C3_2 C4_2 S1_2 -1.8(18) . . . . ?
C1_2 S1_2 C4_2 C3_2 2.3(13) . . . . ?

####################################################################### 
# 
# 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_Eisenreich_TSC_20_a
_database_code_depnum_ccdc_archive 'CCDC 2358071'
loop_
_audit_author_name
_audit_author_address
'Burkhard Butschke'
;Albert Ludwigs Universitaet Freiburg
Germany
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V137 by Daniel Kratzert, Freiburg 2024, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C12 H11 N3 O S'
_chemical_formula_moiety         'C12 H11 N3 O S'
_chemical_formula_weight         245.30
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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'

_cell_length_a                   5.823(2)
_cell_length_b                   9.744(4)
_cell_length_c                   11.011(4)
_cell_angle_alpha                70.013(9)
_cell_angle_beta                 83.399(9)
_cell_angle_gamma                88.167(8)
_cell_volume                     583.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      2.4225
_cell_measurement_theta_max      31.528
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'Crystals were obtained at room temperature from a mixture of dichloromethane and ethanol by slow solvent evaporation.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.747
_exptl_crystal_size_mid          0.387
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7145
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.828
_shelx_estimated_absorpt_T_max   0.964
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_detector                 CCD
_diffrn_detector_type            'Bruker APEXII'
_diffrn_detector_area_resol_mean 8.3
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            34462
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_theta_min         1.980
_diffrn_reflns_theta_max         31.603
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_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             3908
_reflns_number_gt                3506
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'Bruker BIS 2018.9.0.3/05-Dec-2018 and APEX5_2023.9-2'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+0.1615P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3908
_refine_ls_number_parameters     206
_refine_ls_number_restraints     259
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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 -0.01163(4) 0.38303(3) 0.86041(2) 0.01823(7) Uani 1 1 d . . . . .
N1 N 0.42111(14) 0.44530(9) 0.73802(8) 0.01672(15) Uani 1 1 d D . . . .
H1N H 0.545(2) 0.4883(14) 0.7322(13) 0.020 Uiso 1 1 d D U . . .
N2 N 0.29318(15) 0.56806(9) 0.87556(8) 0.01694(16) Uani 1 1 d D . . . .
H2N H 0.196(2) 0.5789(14) 0.9358(12) 0.020 Uiso 1 1 d D U . . .
N3 N 0.49752(14) 0.64522(9) 0.83694(8) 0.01600(15) Uani 1 1 d D . . . .
C1 C 0.24792(16) 0.46839(10) 0.82043(9) 0.01454(16) Uani 1 1 d D . . . .
C2 C 0.41324(16) 0.35844(10) 0.65779(9) 0.01468(16) Uani 1 1 d D . . . .
C3 C 0.23292(17) 0.37078(10) 0.58195(9) 0.01729(17) Uani 1 1 d . . . . .
H3 H 0.107091 0.433886 0.586793 0.021 Uiso 1 1 calc R U . . .
C4 C 0.23829(18) 0.29003(11) 0.49899(9) 0.01984(18) Uani 1 1 d . . . . .
H4 H 0.115388 0.298028 0.447266 0.024 Uiso 1 1 calc R U . . .
C5 C 0.42246(18) 0.19767(11) 0.49132(9) 0.01982(19) Uani 1 1 d . . . . .
H5 H 0.425321 0.142677 0.434646 0.024 Uiso 1 1 calc R U . . .
C6 C 0.60190(18) 0.18630(11) 0.56686(10) 0.02038(19) Uani 1 1 d . . . . .
H6 H 0.727747 0.123283 0.561801 0.024 Uiso 1 1 calc R U . . .
C7 C 0.59859(17) 0.26688(11) 0.65022(10) 0.01841(18) Uani 1 1 d . . . . .
H7 H 0.722084 0.259282 0.701470 0.022 Uiso 1 1 calc R U . . .
C8 C 0.52409(17) 0.74231(10) 0.88977(9) 0.01726(17) Uani 1 1 d D . . . .
H8 H 0.408591 0.751166 0.954946 0.021 Uiso 1 1 calc R U . A 1
O1_1 O 0.8900(6) 0.8176(4) 0.7604(4) 0.0213(7) Uani 0.595(6) 1 d D U P B 1
C1_1 C 1.0577(5) 0.9200(3) 0.7433(3) 0.0240(5) Uani 0.595(6) 1 d D U P B 1
H1_1 H 1.195877 0.931366 0.685686 0.029 Uiso 0.595(6) 1 calc R U P B 1
C2_1 C 1.0017(6) 1.0022(4) 0.8184(4) 0.0242(6) Uani 0.595(6) 1 d D U P B 1
H2_1 H 1.090004 1.080525 0.822480 0.029 Uiso 0.595(6) 1 calc R U P B 1
C3_1 C 0.7848(11) 0.9494(8) 0.8906(7) 0.0231(8) Uani 0.595(6) 1 d D U P B 1
H3_1 H 0.699976 0.984947 0.952499 0.028 Uiso 0.595(6) 1 calc R U P B 1
C4_1 C 0.7235(13) 0.8380(10) 0.8532(10) 0.0158(10) Uani 0.595(6) 1 d D U P B 1
O1_2 O 0.7404(11) 0.9365(9) 0.9037(8) 0.0221(10) Uani 0.405(6) 1 d D U P B 2
C1_2 C 0.9464(9) 1.0078(5) 0.8557(5) 0.0234(8) Uani 0.405(6) 1 d D U P B 2
H1_2 H 0.996973 1.087864 0.876714 0.028 Uiso 0.405(6) 1 calc R U P B 2
C2_2 C 1.0671(7) 0.9494(5) 0.7750(4) 0.0228(7) Uani 0.405(6) 1 d D U P B 2
H2_2 H 1.215175 0.980229 0.729040 0.027 Uiso 0.405(6) 1 calc R U P B 2
C3_2 C 0.9313(13) 0.8318(9) 0.7709(8) 0.0192(9) Uani 0.405(6) 1 d D U P B 2
H3_2 H 0.972286 0.769256 0.722111 0.023 Uiso 0.405(6) 1 calc R U P B 2
C4_2 C 0.7346(19) 0.8265(15) 0.8494(14) 0.0165(13) Uani 0.405(6) 1 d D U P B 2


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 1.6873(11) . ?
N1 C1 1.3439(12) . ?
N1 C2 1.4218(12) . ?
N1 H1N 0.831(11) . ?
N2 C1 1.3555(12) . ?
N2 N3 1.3727(12) . ?
N2 H2N 0.853(11) . ?
N3 C8 1.2899(12) . ?
C2 C7 1.3916(14) . ?
C2 C3 1.3926(14) . ?
C3 C4 1.3920(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.3917(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3876(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.3953(14) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C4_2 1.436(8) . ?
C8 C4_1 1.444(5) . ?
C8 H8 0.9500 . ?
O1_1 C1_1 1.369(3) . ?
O1_1 C4_1 1.386(7) . ?
C1_1 C2_1 1.344(4) . ?
C1_1 H1_1 0.9500 . ?
C2_1 C3_1 1.422(6) . ?
C2_1 H2_1 0.9500 . ?
C3_1 C4_1 1.356(8) . ?
C3_1 H3_1 0.9500 . ?
O1_2 C1_2 1.363(5) . ?
O1_2 C4_2 1.397(11) . ?
C1_2 C2_2 1.336(5) . ?
C1_2 H1_2 0.9500 . ?
C2_2 C3_2 1.429(7) . ?
C2_2 H2_2 0.9500 . ?
C3_2 C4_2 1.344(11) . ?
C3_2 H3_2 0.9500 . ?

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 N1 C2 127.07(8) . . ?
C1 N1 H1N 116.1(9) . . ?
C2 N1 H1N 116.8(9) . . ?
C1 N2 N3 119.42(8) . . ?
C1 N2 H2N 119.1(9) . . ?
N3 N2 H2N 121.4(9) . . ?
C8 N3 N2 115.84(8) . . ?
N1 C1 N2 115.33(8) . . ?
N1 C1 S1 125.59(7) . . ?
N2 C1 S1 119.07(7) . . ?
C7 C2 C3 120.34(9) . . ?
C7 C2 N1 118.23(8) . . ?
C3 C2 N1 121.30(8) . . ?
C4 C3 C2 119.56(9) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.45(9) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 119.67(9) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 120.40(9) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 119.58(9) . . ?
C2 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
N3 C8 C4_2 117.0(5) . . ?
N3 C8 C4_1 122.2(3) . . ?
N3 C8 H8 118.9 . . ?
C4_1 C8 H8 118.9 . . ?
C1_1 O1_1 C4_1 105.1(4) . . ?
C2_1 C1_1 O1_1 111.3(3) . . ?
C2_1 C1_1 H1_1 124.3 . . ?
O1_1 C1_1 H1_1 124.3 . . ?
C1_1 C2_1 C3_1 106.8(3) . . ?
C1_1 C2_1 H2_1 126.6 . . ?
C3_1 C2_1 H2_1 126.6 . . ?
C4_1 C3_1 C2_1 106.2(5) . . ?
C4_1 C3_1 H3_1 126.9 . . ?
C2_1 C3_1 H3_1 126.9 . . ?
C3_1 C4_1 O1_1 110.6(4) . . ?
C3_1 C4_1 C8 132.8(6) . . ?
O1_1 C4_1 C8 116.6(5) . . ?
C1_2 O1_2 C4_2 106.5(6) . . ?
C2_2 C1_2 O1_2 110.5(5) . . ?
C2_2 C1_2 H1_2 124.8 . . ?
O1_2 C1_2 H1_2 124.8 . . ?
C1_2 C2_2 C3_2 107.0(5) . . ?
C1_2 C2_2 H2_2 126.5 . . ?
C3_2 C2_2 H2_2 126.5 . . ?
C4_2 C3_2 C2_2 106.9(6) . . ?
C4_2 C3_2 H3_2 126.5 . . ?
C2_2 C3_2 H3_2 126.5 . . ?
C3_2 C4_2 O1_2 109.1(7) . . ?
C3_2 C4_2 C8 137.9(9) . . ?
O1_2 C4_2 C8 113.0(8) . . ?

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
C1 N2 N3 C8 177.21(8) . . . . ?
C2 N1 C1 N2 -173.37(9) . . . . ?
C2 N1 C1 S1 7.58(14) . . . . ?
N3 N2 C1 N1 5.33(13) . . . . ?
N3 N2 C1 S1 -175.56(7) . . . . ?
C1 N1 C2 C7 -136.66(10) . . . . ?
C1 N1 C2 C3 47.43(14) . . . . ?
C7 C2 C3 C4 0.46(14) . . . . ?
N1 C2 C3 C4 176.28(9) . . . . ?
C2 C3 C4 C5 -0.14(15) . . . . ?
C3 C4 C5 C6 -0.07(15) . . . . ?
C4 C5 C6 C7 -0.03(15) . . . . ?
C3 C2 C7 C6 -0.56(14) . . . . ?
N1 C2 C7 C6 -176.50(9) . . . . ?
C5 C6 C7 C2 0.34(15) . . . . ?
N2 N3 C8 C4_2 -178.9(8) . . . . ?
N2 N3 C8 C4_1 -176.2(6) . . . . ?
C4_1 O1_1 C1_1 C2_1 -0.9(6) . . . . ?
O1_1 C1_1 C2_1 C3_1 0.7(5) . . . . ?
C1_1 C2_1 C3_1 C4_1 -0.3(8) . . . . ?
C2_1 C3_1 C4_1 O1_1 -0.2(11) . . . . ?
C2_1 C3_1 C4_1 C8 -179.5(10) . . . . ?
C1_1 O1_1 C4_1 C3_1 0.7(10) . . . . ?
C1_1 O1_1 C4_1 C8 -180.0(7) . . . . ?
N3 C8 C4_1 C3_1 177.3(10) . . . . ?
N3 C8 C4_1 O1_1 -1.8(12) . . . . ?
C4_2 O1_2 C1_2 C2_2 0.3(10) . . . . ?
O1_2 C1_2 C2_2 C3_2 -0.4(6) . . . . ?
C1_2 C2_2 C3_2 C4_2 0.3(10) . . . . ?
C2_2 C3_2 C4_2 O1_2 -0.2(14) . . . . ?
C2_2 C3_2 C4_2 C8 178.6(17) . . . . ?
C1_2 O1_2 C4_2 C3_2 -0.1(14) . . . . ?
C1_2 O1_2 C4_2 C8 -179.1(10) . . . . ?
N3 C8 C4_2 C3_2 -3(2) . . . . ?
N3 C8 C4_2 O1_2 175.2(8) . . . . ?

####################################################################### 
# 
# 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_Eisenreich_TSC_14_a
_database_code_depnum_ccdc_archive 'CCDC 2358069'
loop_
_audit_author_name
_audit_author_address
'Burkhard Butschke'
;Albert Ludwigs Universitaet Freiburg
Germany
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V137 by Daniel Kratzert, Freiburg 2024, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C14 H8 F5 N3 S'
_chemical_formula_moiety         'C14 H8 F5 N3 S'
_chemical_formula_weight         345.29
_chemical_melting_point          ?
_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                   28.980(9)
_cell_length_b                   6.951(3)
_cell_length_c                   14.974(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.329(11)
_cell_angle_gamma                90
_cell_volume                     2828.4(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      2.7645
_cell_measurement_theta_max      30.949
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'Crystals were obtained at room temperature from a mixture of dichloromethane and ethanol by slow solvent evaporation.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6993
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_detector                 CCD
_diffrn_detector_type            'Bruker APEXII'
_diffrn_detector_area_resol_mean 8.3
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            62608
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_theta_min         1.499
_diffrn_reflns_theta_max         31.503
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4708
_reflns_number_gt                3855
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'Bruker BIS 2018.9.0.3/05-Dec-2018 and APEX5_2023.9-2'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+3.3599P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4708
_refine_ls_number_parameters     214
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'
F F 0.0171 0.0103 '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'

_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_
_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 0.42126(2) 0.92329(5) 0.67147(2) 0.01871(8) Uani 1 1 d . . . . .
F1 F 0.65881(3) 0.61260(14) 0.65469(6) 0.02350(19) Uani 1 1 d . . . . .
F2 F 0.71169(3) 0.51860(15) 0.54450(7) 0.0275(2) Uani 1 1 d . . . . .
F3 F 0.66651(3) 0.49194(15) 0.35179(7) 0.0286(2) Uani 1 1 d . . . . .
F4 F 0.56928(3) 0.57034(14) 0.27110(6) 0.02466(19) Uani 1 1 d . . . . .
F5 F 0.51627(3) 0.67164(13) 0.37826(6) 0.02081(18) Uani 1 1 d . . . . .
N1 N 0.42298(4) 0.84915(17) 0.49396(8) 0.0174(2) Uani 1 1 d D . . . .
H1N H 0.4437(5) 0.816(3) 0.4668(11) 0.021 Uiso 1 1 d D U . . .
N2 N 0.49383(4) 0.80432(18) 0.61892(8) 0.0180(2) Uani 1 1 d D . . . .
H2N H 0.5120(6) 0.822(3) 0.6765(9) 0.022 Uiso 1 1 d D U . . .
N3 N 0.51433(4) 0.75133(17) 0.55281(8) 0.0168(2) Uani 1 1 d D . . . .
C1 C 0.44546(5) 0.85830(19) 0.58880(9) 0.0156(2) Uani 1 1 d D . . . .
C2 C 0.37411(5) 0.88826(19) 0.43285(10) 0.0173(2) Uani 1 1 d D . . . .
C3 C 0.33471(5) 0.9280(2) 0.46308(11) 0.0238(3) Uani 1 1 d . . . . .
H3 H 0.339243 0.930893 0.529028 0.029 Uiso 1 1 calc R U . . .
C4 C 0.28847(5) 0.9635(3) 0.39479(12) 0.0295(3) Uani 1 1 d . . . . .
H4 H 0.261496 0.990801 0.414981 0.035 Uiso 1 1 calc R U . . .
C5 C 0.28103(6) 0.9599(3) 0.29834(12) 0.0307(3) Uani 1 1 d . . . . .
H5 H 0.249364 0.985291 0.252874 0.037 Uiso 1 1 calc R U . . .
C6 C 0.32045(6) 0.9186(3) 0.26876(12) 0.0300(3) Uani 1 1 d . . . . .
H6 H 0.315739 0.915012 0.202748 0.036 Uiso 1 1 calc R U . . .
C7 C 0.36672(5) 0.8827(2) 0.33573(10) 0.0229(3) Uani 1 1 d . . . . .
H7 H 0.393512 0.854153 0.315205 0.027 Uiso 1 1 calc R U . . .
C8 C 0.55987(5) 0.70266(19) 0.58550(9) 0.0160(2) Uani 1 1 d . . . . .
H8 H 0.577050 0.703581 0.652308 0.019 Uiso 1 1 calc R U . . .
C9 C 0.58565(4) 0.64588(19) 0.52140(9) 0.0149(2) Uani 1 1 d . . . . .
C10 C 0.63592(5) 0.60412(19) 0.56002(9) 0.0168(2) Uani 1 1 d . . . . .
C11 C 0.66347(5) 0.5542(2) 0.50437(10) 0.0190(3) Uani 1 1 d . . . . .
C12 C 0.64070(5) 0.5416(2) 0.40684(10) 0.0199(3) Uani 1 1 d . . . . .
C13 C 0.59096(5) 0.5815(2) 0.36570(9) 0.0179(2) Uani 1 1 d . . . . .
C14 C 0.56404(5) 0.63278(19) 0.42207(9) 0.0156(2) Uani 1 1 d . . . . .


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 1.6828(14) . ?
F1 C10 1.3416(16) . ?
F2 C11 1.3385(15) . ?
F3 C12 1.3366(15) . ?
F4 C13 1.3375(16) . ?
F5 C14 1.3376(15) . ?
N1 C1 1.3425(18) . ?
N1 C2 1.4201(17) . ?
N1 H1N 0.865(13) . ?
N2 C1 1.3673(17) . ?
N2 N3 1.3701(15) . ?
N2 H2N 0.849(13) . ?
N3 C8 1.2833(17) . ?
C2 C3 1.3945(19) . ?
C2 C7 1.395(2) . ?
C3 C4 1.397(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.4606(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3985(18) . ?
C9 C14 1.4019(18) . ?
C10 C11 1.3837(18) . ?
C11 C12 1.381(2) . ?
C12 C13 1.3846(19) . ?
C13 C14 1.3806(18) . ?

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 N1 C2 132.95(11) . . ?
C1 N1 H1N 110.4(11) . . ?
C2 N1 H1N 116.6(11) . . ?
C1 N2 N3 119.19(11) . . ?
C1 N2 H2N 120.0(11) . . ?
N3 N2 H2N 120.0(11) . . ?
C8 N3 N2 116.23(11) . . ?
N1 C1 N2 113.64(11) . . ?
N1 C1 S1 128.15(10) . . ?
N2 C1 S1 118.20(10) . . ?
C3 C2 C7 119.83(13) . . ?
C3 C2 N1 125.07(13) . . ?
C7 C2 N1 115.10(12) . . ?
C2 C3 C4 118.88(14) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 121.52(14) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 119.23(14) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 120.04(15) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.50(14) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N3 C8 C9 120.90(12) . . ?
N3 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C14 116.25(11) . . ?
C10 C9 C8 118.78(11) . . ?
C14 C9 C8 124.95(11) . . ?
F1 C10 C11 118.06(11) . . ?
F1 C10 C9 119.31(11) . . ?
C11 C10 C9 122.63(12) . . ?
F2 C11 C12 120.26(12) . . ?
F2 C11 C10 120.45(12) . . ?
C12 C11 C10 119.29(12) . . ?
F3 C12 C11 120.30(12) . . ?
F3 C12 C13 119.76(13) . . ?
C11 C12 C13 119.94(12) . . ?
F4 C13 C14 120.34(12) . . ?
F4 C13 C12 119.54(12) . . ?
C14 C13 C12 120.12(12) . . ?
F5 C14 C13 117.44(12) . . ?
F5 C14 C9 120.79(11) . . ?
C13 C14 C9 121.77(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
C1 N2 N3 C8 179.84(12) . . . . ?
C2 N1 C1 N2 179.12(13) . . . . ?
C2 N1 C1 S1 0.1(2) . . . . ?
N3 N2 C1 N1 1.04(18) . . . . ?
N3 N2 C1 S1 -179.83(10) . . . . ?
C1 N1 C2 C3 -8.0(2) . . . . ?
C1 N1 C2 C7 172.70(14) . . . . ?
C7 C2 C3 C4 -0.6(2) . . . . ?
N1 C2 C3 C4 -179.87(14) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C2 -0.2(2) . . . . ?
C3 C2 C7 C6 0.7(2) . . . . ?
N1 C2 C7 C6 -179.97(14) . . . . ?
N2 N3 C8 C9 -179.24(12) . . . . ?
N3 C8 C9 C10 176.57(13) . . . . ?
N3 C8 C9 C14 -2.2(2) . . . . ?
C14 C9 C10 F1 -179.53(12) . . . . ?
C8 C9 C10 F1 1.63(19) . . . . ?
C14 C9 C10 C11 0.6(2) . . . . ?
C8 C9 C10 C11 -178.24(13) . . . . ?
F1 C10 C11 F2 -1.0(2) . . . . ?
C9 C10 C11 F2 178.88(13) . . . . ?
F1 C10 C11 C12 179.05(13) . . . . ?
C9 C10 C11 C12 -1.1(2) . . . . ?
F2 C11 C12 F3 0.7(2) . . . . ?
C10 C11 C12 F3 -179.39(13) . . . . ?
F2 C11 C12 C13 -179.02(13) . . . . ?
C10 C11 C12 C13 0.9(2) . . . . ?
F3 C12 C13 F4 -0.2(2) . . . . ?
C11 C12 C13 F4 179.50(13) . . . . ?
F3 C12 C13 C14 179.95(13) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
F4 C13 C14 F5 -0.57(19) . . . . ?
C12 C13 C14 F5 179.30(12) . . . . ?
F4 C13 C14 C9 -179.97(12) . . . . ?
C12 C13 C14 C9 -0.1(2) . . . . ?
C10 C9 C14 F5 -179.38(12) . . . . ?
C8 C9 C14 F5 -0.6(2) . . . . ?
C10 C9 C14 C13 0.00(19) . . . . ?
C8 C9 C14 C13 178.75(13) . . . . ?

