# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_av098
_database_code_depnum_ccdc_archive 'CCDC 2254388'
loop_
_audit_author_name
_audit_author_address
'Peter Mayer'
;LMU Muenchen
Germany
;



_audit_update_record             
;
2023-04-06 deposited with the CCDC.	2023-05-10 downloaded from the CCDC.
;

_chemical_name_common            unknowncrystal
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.150 #?# in millimeters
_exptl_crystal_size_mid          0.130 #?# in millimeters
_exptl_crystal_size_min          0.040 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      173.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.3910

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   18.5673(6)
_cell_length_b                   5.8814(2)
_cell_length_c                   15.1443(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.7200(10)
_cell_angle_gamma                90
_cell_volume                     1630.04(10)
_cell_measurement_temperature    173.(2) #?# in K
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.7291
_cell_measurement_theta_max      27.4914
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_diffrn_reflns_number            27725 #xl
_diffrn_reflns_av_R_equivalents  0.0415 #xl
_diffrn_reflns_av_unetI/netI     0.0257 #xl
_diffrn_reflns_limit_h_min       -24 #xl
_diffrn_reflns_limit_h_max       24 #xl
_diffrn_reflns_limit_k_min       -7 #xl
_diffrn_reflns_limit_k_max       7 #xl
_diffrn_reflns_limit_l_min       -19 #xl
_diffrn_reflns_limit_l_max       19 #xl
_diffrn_reflns_theta_min         3.117 #xl
_diffrn_reflns_theta_max         27.482 #xl
_diffrn_measured_fraction_theta_max 0.999 #xl
_diffrn_reflns_theta_full        25.242 #xl
_diffrn_measured_fraction_theta_full 0.998 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.999 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.998 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.999 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.998 #xl

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

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'

_reflns_number_total             3740 #xl
_reflns_number_gt                3312 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_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.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+0.7093P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         3740 #xl
_refine_ls_number_parameters     194 #xl
_refine_ls_number_restraints     0 #xl
_refine_ls_R_factor_all          0.0419 #xl
_refine_ls_R_factor_gt           0.0359 #xl
_refine_ls_wR_factor_ref         0.0924 #xl
_refine_ls_wR_factor_gt          0.0892 #xl
_refine_ls_goodness_of_fit_ref   1.104 #xl
_refine_ls_restrained_S_all      1.104 #xl
_refine_ls_shift/su_max          0.001 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.276 #xl
_refine_diff_density_min         -0.217 #xl
_refine_diff_density_rms         0.041 #xl

_refine_special_details          
;
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'

_computing_publication_material  ?

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.03487(8) 0.0884(3) 0.65177(10) 0.0331(3) Uani 1 1 d . . . . .
C2 C 0.05962(8) -0.1412(3) 0.63556(10) 0.0303(3) Uani 1 1 d . . . . .
H2A H 0.043277 -0.182001 0.571906 0.036 Uiso 1 1 calc R U . . .
H2AB H 0.037630 -0.250829 0.672910 0.036 Uiso 1 1 calc R U . . .
C3 C 0.18011(7) 0.0024(2) 0.57245(8) 0.0217(3) Uani 1 1 d . . . . .
C4 C 0.25849(7) 0.0779(2) 0.57424(8) 0.0207(3) Uani 1 1 d . . . . .
C5 C 0.16964(7) 0.2046(2) 0.44617(9) 0.0224(3) Uani 1 1 d . . . . .
C6 C 0.30398(7) 0.3070(2) 0.45875(9) 0.0227(3) Uani 1 1 d . . . . .
H6 H 0.351215 0.274933 0.491386 0.027 Uiso 1 1 calc R U . . .
C7 C 0.30215(7) 0.4586(2) 0.39209(9) 0.0242(3) Uani 1 1 d . . . . .
H7 H 0.256296 0.493158 0.356432 0.029 Uiso 1 1 calc R U . . .
C8 C 0.36742(7) 0.5733(2) 0.37174(8) 0.0231(3) Uani 1 1 d . . . . .
C9 C 0.43779(7) 0.4824(3) 0.39295(9) 0.0273(3) Uani 1 1 d . . . . .
H9 H 0.444450 0.337231 0.420661 0.033 Uiso 1 1 calc R U . . .
C10 C 0.49801(8) 0.6006(3) 0.37418(10) 0.0333(3) Uani 1 1 d . . . . .
H10 H 0.545382 0.536108 0.389552 0.040 Uiso 1 1 calc R U . . .
C11 C 0.48985(8) 0.8113(3) 0.33334(10) 0.0344(3) Uani 1 1 d . . . . .
H11 H 0.531253 0.891648 0.320523 0.041 Uiso 1 1 calc R U . . .
C12 C 0.42062(9) 0.9037(3) 0.31135(10) 0.0336(3) Uani 1 1 d . . . . .
H12 H 0.414424 1.048238 0.283113 0.040 Uiso 1 1 calc R U . . .
C13 C 0.36025(8) 0.7865(3) 0.33026(9) 0.0287(3) Uani 1 1 d . . . . .
H13 H 0.313087 0.852377 0.314749 0.034 Uiso 1 1 calc R U . . .
C14 C 0.28254(8) 0.2439(2) 0.65152(9) 0.0276(3) Uani 1 1 d . . . . .
H14A H 0.329660 0.311336 0.645193 0.041 Uiso 1 1 calc R U . . .
H14B H 0.287438 0.162164 0.708614 0.041 Uiso 1 1 calc R U . . .
H14C H 0.245903 0.364333 0.650187 0.041 Uiso 1 1 calc R U . . .
C15 C 0.31109(8) -0.1232(2) 0.57827(10) 0.0296(3) Uani 1 1 d . . . . .
H15A H 0.359282 -0.068702 0.569575 0.044 Uiso 1 1 calc R U . . .
H15B H 0.292477 -0.232294 0.530985 0.044 Uiso 1 1 calc R U . . .
H15C H 0.315244 -0.197516 0.636827 0.044 Uiso 1 1 calc R U . . .
C16 C 0.15689(8) 0.0989(3) 0.35264(9) 0.0313(3) Uani 1 1 d . . . . .
H16A H 0.174328 -0.058668 0.356377 0.047 Uiso 1 1 calc R U . . .
H16B H 0.183602 0.186025 0.313456 0.047 Uiso 1 1 calc R U . . .
H16C H 0.104554 0.101453 0.328131 0.047 Uiso 1 1 calc R U . . .
C17 C 0.13749(8) 0.4432(3) 0.44685(11) 0.0340(3) Uani 1 1 d . . . . .
H17A H 0.150259 0.508499 0.506995 0.051 Uiso 1 1 calc R U . . .
H17B H 0.084210 0.435202 0.430189 0.051 Uiso 1 1 calc R U . . .
H17C H 0.157365 0.539105 0.403816 0.051 Uiso 1 1 calc R U . . .
N1 N 0.01703(8) 0.2686(3) 0.66648(11) 0.0476(4) Uani 1 1 d . . . . .
N2 N 0.13320(6) 0.06403(19) 0.50611(7) 0.0235(2) Uani 1 1 d . . . . .
N3 N 0.24774(6) 0.1917(2) 0.48658(7) 0.0237(2) Uani 1 1 d . . . . .
S1 S 0.15850(2) -0.15927(6) 0.66218(2) 0.02729(10) 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
C1 N1 1.144(2) . ?
C1 C2 1.460(2) . ?
C2 S1 1.8151(15) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 N2 1.2664(17) . ?
C3 C4 1.5174(17) . ?
C3 S1 1.7595(13) . ?
C4 N3 1.4699(16) . ?
C4 C15 1.5285(19) . ?
C4 C14 1.5314(18) . ?
C5 N2 1.4741(16) . ?
C5 N3 1.4776(16) . ?
C5 C17 1.525(2) . ?
C5 C16 1.5284(19) . ?
C6 C7 1.3433(19) . ?
C6 N3 1.3698(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.4645(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3982(19) . ?
C8 C13 1.399(2) . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 178.08(18) . . ?
C1 C2 S1 110.60(10) . . ?
C1 C2 H2A 109.5 . . ?
S1 C2 H2A 109.5 . . ?
C1 C2 H2AB 109.5 . . ?
S1 C2 H2AB 109.5 . . ?
H2A C2 H2AB 108.1 . . ?
N2 C3 C4 117.36(11) . . ?
N2 C3 S1 123.46(10) . . ?
C4 C3 S1 119.17(9) . . ?
N3 C4 C3 97.67(9) . . ?
N3 C4 C15 112.13(11) . . ?
C3 C4 C15 112.26(11) . . ?
N3 C4 C14 112.18(11) . . ?
C3 C4 C14 110.80(11) . . ?
C15 C4 C14 111.15(11) . . ?
N2 C5 N3 103.67(10) . . ?
N2 C5 C17 106.92(11) . . ?
N3 C5 C17 113.72(11) . . ?
N2 C5 C16 109.09(11) . . ?
N3 C5 C16 110.52(11) . . ?
C17 C5 C16 112.40(12) . . ?
C7 C6 N3 129.49(12) . . ?
C7 C6 H6 115.3 . . ?
N3 C6 H6 115.3 . . ?
C6 C7 C8 123.18(12) . . ?
C6 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C9 C8 C13 117.42(12) . . ?
C9 C8 C7 123.36(13) . . ?
C13 C8 C7 119.22(12) . . ?
C10 C9 C8 121.05(14) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 120.68(14) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.16(14) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C13 120.40(14) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 121.29(14) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 C17 H17A 109.5 . . ?
C5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 N2 C5 108.87(11) . . ?
C6 N3 C4 120.59(10) . . ?
C6 N3 C5 126.36(11) . . ?
C4 N3 C5 111.82(10) . . ?
C3 S1 C2 98.68(6) . . ?

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
N2 C3 C4 N3 -3.64(15) . . . . ?
S1 C3 C4 N3 177.60(9) . . . . ?
N2 C3 C4 C15 -121.40(13) . . . . ?
S1 C3 C4 C15 59.83(14) . . . . ?
N2 C3 C4 C14 113.67(13) . . . . ?
S1 C3 C4 C14 -65.10(13) . . . . ?
N3 C6 C7 C8 178.29(13) . . . . ?
C6 C7 C8 C9 25.4(2) . . . . ?
C6 C7 C8 C13 -153.57(14) . . . . ?
C13 C8 C9 C10 0.6(2) . . . . ?
C7 C8 C9 C10 -178.38(13) . . . . ?
C8 C9 C10 C11 -0.5(2) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
C11 C12 C13 C8 0.0(2) . . . . ?
C9 C8 C13 C12 -0.3(2) . . . . ?
C7 C8 C13 C12 178.67(13) . . . . ?
C4 C3 N2 C5 -1.22(16) . . . . ?
S1 C3 N2 C5 177.49(9) . . . . ?
N3 C5 N2 C3 5.55(14) . . . . ?
C17 C5 N2 C3 -114.90(12) . . . . ?
C16 C5 N2 C3 123.32(12) . . . . ?
C7 C6 N3 C4 -164.38(14) . . . . ?
C7 C6 N3 C5 1.9(2) . . . . ?
C3 C4 N3 C6 175.14(12) . . . . ?
C15 C4 N3 C6 -67.00(16) . . . . ?
C14 C4 N3 C6 58.91(16) . . . . ?
C3 C4 N3 C5 7.05(13) . . . . ?
C15 C4 N3 C5 124.91(12) . . . . ?
C14 C4 N3 C5 -109.18(12) . . . . ?
N2 C5 N3 C6 -175.40(12) . . . . ?
C17 C5 N3 C6 -59.68(18) . . . . ?
C16 C5 N3 C6 67.83(17) . . . . ?
N2 C5 N3 C4 -8.15(14) . . . . ?
C17 C5 N3 C4 107.58(13) . . . . ?
C16 C5 N3 C4 -124.92(12) . . . . ?
N2 C3 S1 C2 -10.66(13) . . . . ?
C4 C3 S1 C2 168.03(10) . . . . ?
C1 C2 S1 C3 -70.84(11) . . . . ?

_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.
;

_audit_block_code                C17H21N3S_av098_ofial
_audit_creation_method           'APEX3 v2018.7-2'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H21 N3 S'
_chemical_formula_sum            'C17 H21 N3 S'
_chemical_formula_weight         299.43 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            4 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             640 #?# check!


