# Supplementary Information (SI) for CrystEngComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2481860'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Universitat de les Illes Balears
Spain
;
_audit_update_record             
;
2025-08-21 deposited with the CCDC.	2025-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H23 N3 O S'
_chemical_formula_sum            'C18 H23 N3 O S'
_chemical_formula_weight         329.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   14.2535(3)
_cell_length_b                   6.5278(2)
_cell_length_c                   18.3623(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.641(2)
_cell_angle_gamma                90
_cell_volume                     1667.09(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    16945
_cell_measurement_theta_min      3.5960
_cell_measurement_theta_max      79.1020

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.043

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.0253
1 0 -1 0.0173
1 0 1 0.0505
-1 0 -1 0.0545
0 -1 0 0.1648
0 1 0 0.1648
0 0 -1 0.0542
0 0 1 0.0592

_exptl_absorpt_coefficient_mu    1.782
_shelx_estimated_absorpt_T_min   0.591
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_reflns_number            40669
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.571
_diffrn_reflns_theta_max         74.626
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             40669
_reflns_number_gt                37646
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPRO (OD, 2024)'
_computing_cell_refinement       'CrysAlisPRO (OD, 2024)'
_computing_data_reduction        'CrysAlisPRO (OD, 2024)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2015b)'
_refine_special_details          
;
Owing to poor agreement, one reflection, i.e. (7 -2 -9), 
was omitted from the final cycles of refinement.
Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0576P)²+0.2719P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         40669
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.68709(2) -0.20262(7) 0.36419(2) 0.03213(15) Uani 1 1 d . . . . .
O1 O 1.09198(7) 0.26365(19) 0.60787(6) 0.0270(3) Uani 1 1 d . . . . .
H1O H 1.149(2) 0.284(4) 0.6255(13) 0.051(6) Uiso 1 1 d . . . . .
N1 N 0.64049(8) 0.1506(2) 0.42559(7) 0.0239(3) Uani 1 1 d . . . . .
H1N H 0.6642(14) 0.250(4) 0.4509(11) 0.029(5) Uiso 1 1 d . . . . .
N2 N 0.79657(9) 0.0497(2) 0.45737(7) 0.0255(3) Uani 1 1 d . . . . .
H2N H 0.8402(15) -0.037(4) 0.4531(10) 0.032(5) Uiso 1 1 d . . . . .
N3 N 0.81782(8) 0.2281(2) 0.49743(6) 0.0220(3) Uani 1 1 d . . . . .
C1 C 0.70583(10) 0.0121(3) 0.41736(8) 0.0233(3) Uani 1 1 d . . . . .
C2 C 0.54199(9) 0.1834(2) 0.38035(7) 0.0197(3) Uani 1 1 d . . . . .
C3 C 0.50262(10) 0.3684(3) 0.41547(7) 0.0230(3) Uani 1 1 d . . . . .
H3A H 0.545409 0.487785 0.415281 0.028 Uiso 1 1 calc R U . . .
H3B H 0.500917 0.337199 0.467923 0.028 Uiso 1 1 calc R U . . .
C4 C 0.40083(10) 0.4203(3) 0.37142(8) 0.0249(3) Uani 1 1 d . . . . .
H4 H 0.375665 0.541425 0.394492 0.030 Uiso 1 1 calc R U . . .
C5 C 0.33492(10) 0.2361(3) 0.37276(8) 0.0283(3) Uani 1 1 d . . . . .
H5A H 0.269169 0.268427 0.344429 0.034 Uiso 1 1 calc R U . . .
H5B H 0.331635 0.204587 0.424886 0.034 Uiso 1 1 calc R U . . .
C6 C 0.37398(9) 0.0506(3) 0.33794(8) 0.0246(3) Uani 1 1 d . . . . .
H6 H 0.330752 -0.069625 0.338734 0.030 Uiso 1 1 calc R U . . .
C7 C 0.47583(9) -0.0007(2) 0.38261(8) 0.0228(3) Uani 1 1 d . . . . .
H7A H 0.473873 -0.032606 0.434965 0.027 Uiso 1 1 calc R U . . .
H7B H 0.500813 -0.122289 0.360779 0.027 Uiso 1 1 calc R U . . .
C8 C 0.54553(9) 0.2352(3) 0.29958(7) 0.0215(3) Uani 1 1 d . . . . .
H8A H 0.571795 0.117472 0.276466 0.026 Uiso 1 1 calc R U . . .
H8B H 0.588107 0.354554 0.298721 0.026 Uiso 1 1 calc R U . . .
C9 C 0.44342(10) 0.2845(2) 0.25536(8) 0.0221(3) Uani 1 1 d . . . . .
H9 H 0.445365 0.316656 0.202464 0.027 Uiso 1 1 calc R U . . .
C10 C 0.40500(10) 0.4700(3) 0.29053(8) 0.0248(3) Uani 1 1 d . . . . .
H10A H 0.339907 0.505351 0.261619 0.030 Uiso 1 1 calc R U . . .
H10B H 0.447539 0.589424 0.289534 0.030 Uiso 1 1 calc R U . . .
C11 C 0.37842(9) 0.0994(3) 0.25716(8) 0.0241(3) Uani 1 1 d . . . . .
H11A H 0.403821 -0.020458 0.234613 0.029 Uiso 1 1 calc R U . . .
H11B H 0.312972 0.128973 0.227632 0.029 Uiso 1 1 calc R U . . .
C12 C 0.90741(9) 0.2535(2) 0.52661(7) 0.0207(3) Uani 1 1 d . . . . .
H12 H 0.951581 0.149667 0.520176 0.025 Uiso 1 1 calc R U . . .
C13 C 0.94379(9) 0.4356(2) 0.56920(7) 0.0193(3) Uani 1 1 d . . . . .
C14 C 0.88774(9) 0.6102(3) 0.57112(7) 0.0226(3) Uani 1 1 d . . . . .
H14 H 0.822585 0.611052 0.544509 0.027 Uiso 1 1 calc R U . . .
C15 C 0.92555(11) 0.7816(3) 0.61110(8) 0.0254(3) Uani 1 1 d . . . . .
H15 H 0.886386 0.898634 0.612538 0.031 Uiso 1 1 calc R U . . .
C16 C 1.02169(11) 0.7819(3) 0.64940(8) 0.0254(3) Uani 1 1 d . . . . .
H16 H 1.048110 0.900192 0.676399 0.031 Uiso 1 1 calc R U . . .
C17 C 1.07861(9) 0.6111(3) 0.64826(7) 0.0230(3) Uani 1 1 d . . . . .
H17 H 1.143931 0.611980 0.674474 0.028 Uiso 1 1 calc R U . . .
C18 C 1.04013(9) 0.4381(2) 0.60870(7) 0.0203(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.6958(16) . ?
O1 C18 1.3597(19) . ?
O1 H1O 0.82(3) . ?
N1 C1 1.330(2) . ?
N1 C2 1.4820(17) . ?
N1 H1N 0.83(2) . ?
N2 C1 1.3627(18) . ?
N2 N3 1.3751(19) . ?
N2 H2N 0.86(2) . ?
N3 C12 1.2828(18) . ?
C2 C3 1.533(2) . ?
C2 C8 1.5327(19) . ?
C2 C7 1.533(2) . ?
C3 C4 1.5362(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.529(2) . ?
C4 C10 1.534(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.530(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.532(2) . ?
C6 C7 1.5400(18) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5376(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C11 1.528(2) . ?
C9 C10 1.529(2) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.455(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(2) . ?
C13 C18 1.4057(19) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.397(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(2) . ?
C17 H17 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
C18 O1 H1O 111.1(19) . . ?
C1 N1 C2 129.46(13) . . ?
C1 N1 H1N 112.8(14) . . ?
C2 N1 H1N 115.0(14) . . ?
C1 N2 N3 120.85(13) . . ?
C1 N2 H2N 117.1(13) . . ?
N3 N2 H2N 121.8(13) . . ?
C12 N3 N2 114.55(13) . . ?
N1 C1 N2 114.96(14) . . ?
N1 C1 S1 126.95(11) . . ?
N2 C1 S1 118.08(11) . . ?
N1 C2 C3 105.50(11) . . ?
N1 C2 C8 110.27(11) . . ?
C3 C2 C8 109.02(12) . . ?
N1 C2 C7 112.61(12) . . ?
C3 C2 C7 108.79(12) . . ?
C8 C2 C7 110.47(11) . . ?
C2 C3 C4 110.05(11) . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C10 109.64(12) . . ?
C5 C4 C3 109.32(13) . . ?
C10 C4 C3 108.92(11) . . ?
C5 C4 H4 109.6 . . ?
C10 C4 H4 109.6 . . ?
C3 C4 H4 109.6 . . ?
C4 C5 C6 109.53(12) . . ?
C4 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
C5 C6 C11 109.65(13) . . ?
C5 C6 C7 109.65(12) . . ?
C11 C6 C7 109.09(11) . . ?
C5 C6 H6 109.5 . . ?
C11 C6 H6 109.5 . . ?
C7 C6 H6 109.5 . . ?
C2 C7 C6 109.19(12) . . ?
C2 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
C2 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C2 C8 C9 109.24(10) . . ?
C2 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
C2 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C11 C9 C10 110.03(12) . . ?
C11 C9 C8 109.35(12) . . ?
C10 C9 C8 109.15(11) . . ?
C11 C9 H9 109.4 . . ?
C10 C9 H9 109.4 . . ?
C8 C9 H9 109.4 . . ?
C9 C10 C4 109.54(12) . . ?
C9 C10 H10A 109.8 . . ?
C4 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
C4 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C9 C11 C6 109.82(11) . . ?
C9 C11 H11A 109.7 . . ?
C6 C11 H11A 109.7 . . ?
C9 C11 H11B 109.7 . . ?
C6 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N3 C12 C13 122.37(14) . . ?
N3 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C18 118.51(13) . . ?
C14 C13 C12 122.80(12) . . ?
C18 C13 C12 118.68(13) . . ?
C15 C14 C13 121.02(13) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.63(15) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.40(14) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.86(12) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
O1 C18 C17 122.24(12) . . ?
O1 C18 C13 117.17(13) . . ?
C17 C18 C13 120.57(14) . . ?

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 C12 -173.56(13) . . . . ?
C2 N1 C1 N2 165.91(14) . . . . ?
C2 N1 C1 S1 -15.0(2) . . . . ?
N3 N2 C1 N1 -5.4(2) . . . . ?
N3 N2 C1 S1 175.45(11) . . . . ?
C1 N1 C2 C3 -178.46(15) . . . . ?
C1 N1 C2 C8 -60.9(2) . . . . ?
C1 N1 C2 C7 63.0(2) . . . . ?
N1 C2 C3 C4 178.53(12) . . . . ?
C8 C2 C3 C4 60.11(15) . . . . ?
C7 C2 C3 C4 -60.42(15) . . . . ?
C2 C3 C4 C5 59.98(15) . . . . ?
C2 C3 C4 C10 -59.80(17) . . . . ?
C10 C4 C5 C6 59.97(15) . . . . ?
C3 C4 C5 C6 -59.37(15) . . . . ?
C4 C5 C6 C11 -59.75(14) . . . . ?
C4 C5 C6 C7 60.01(15) . . . . ?
N1 C2 C7 C6 176.90(11) . . . . ?
C3 C2 C7 C6 60.33(14) . . . . ?
C8 C2 C7 C6 -59.31(15) . . . . ?
C5 C6 C7 C2 -60.57(15) . . . . ?
C11 C6 C7 C2 59.53(16) . . . . ?
N1 C2 C8 C9 -175.71(13) . . . . ?
C3 C2 C8 C9 -60.33(15) . . . . ?
C7 C2 C8 C9 59.17(16) . . . . ?
C2 C8 C9 C11 -59.43(15) . . . . ?
C2 C8 C9 C10 60.98(16) . . . . ?
C11 C9 C10 C4 59.07(14) . . . . ?
C8 C9 C10 C4 -60.92(15) . . . . ?
C5 C4 C10 C9 -59.53(14) . . . . ?
C3 C4 C10 C9 60.06(16) . . . . ?
C10 C9 C11 C6 -59.02(14) . . . . ?
C8 C9 C11 C6 60.86(15) . . . . ?
C5 C6 C11 C9 59.23(14) . . . . ?
C7 C6 C11 C9 -60.87(16) . . . . ?
N2 N3 C12 C13 178.28(12) . . . . ?
N3 C12 C13 C14 -11.1(2) . . . . ?
N3 C12 C13 C18 170.45(13) . . . . ?
C18 C13 C14 C15 -0.3(2) . . . . ?
C12 C13 C14 C15 -178.73(13) . . . . ?
C13 C14 C15 C16 0.9(2) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C16 C17 C18 O1 -177.66(13) . . . . ?
C16 C17 C18 C13 0.5(2) . . . . ?
C14 C13 C18 O1 177.84(12) . . . . ?
C12 C13 C18 O1 -3.65(18) . . . . ?
C14 C13 C18 C17 -0.44(19) . . . . ?
C12 C13 C18 C17 178.06(12) . . . . ?

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2481862'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Universitat de les Illes Balears
Spain
;
_audit_update_record             
;
2025-08-21 deposited with the CCDC.	2025-10-17 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT230_shelx               
;
PROBLEM: Hirshfeld Test Diff for    S1       --C1       .        7.6 s.u.  
RESPONSE: The chemical composition of the molecule has been established
unambiguously.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 F2 N3 S'
_chemical_formula_sum            'C18 H21 F2 N3 S'
_chemical_formula_weight         349.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   6.36690(10)
_cell_length_b                   11.81400(10)
_cell_length_c                   11.87680(10)
_cell_angle_alpha                78.1450(10)
_cell_angle_beta                 84.2700(10)
_cell_angle_gamma                79.0810(10)
_cell_volume                     856.746(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    16065
_cell_measurement_theta_min      3.8000
_cell_measurement_theta_max      79.3790

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0331
0 1 0 0.0331
0 0 -1 0.0263
0 0 1 0.0263
-4 -3 -3 0.1264
4 3 3 0.1264
0 -5 -3 0.0288
-3 3 -1 0.1176
0 5 -3 0.0268

_exptl_absorpt_coefficient_mu    1.895
_shelx_estimated_absorpt_T_min   0.610
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_reflns_number            20080
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.811
_diffrn_reflns_theta_max         77.362
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3604
_reflns_number_gt                3507
_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       'CrysAlisPRO (OD, 2024)'
_computing_cell_refinement       'CrysAlisPRO (OD, 2024)'
_computing_data_reduction        'CrysAlisPRO (OD, 2024)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2015b)'
_refine_special_details          
;
Owing to poor agreement, one reflection, i.e. (1 0 4), 
was omitted from the final cycles of refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²+0.2439P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3604
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.01601(4) 0.37297(2) 0.87888(2) 0.02822(10) Uani 1 1 d . . . . .
F1 F 1.10170(15) 0.92814(8) 0.78325(9) 0.0549(2) Uani 1 1 d . . . . .
F2 F 0.43978(13) 0.87576(7) 0.97699(7) 0.0429(2) Uani 1 1 d . . . . .
N1 N 0.41113(15) 0.39327(8) 0.77696(8) 0.0252(2) Uani 1 1 d . . . . .
H1N H 0.518(2) 0.4311(13) 0.7721(13) 0.031(4) Uiso 1 1 d . . . . .
N2 N 0.26867(15) 0.51897(8) 0.89702(8) 0.0256(2) Uani 1 1 d . . . . .
H2N H 0.176(3) 0.5429(14) 0.9496(14) 0.039(4) Uiso 1 1 d . . . . .
N3 N 0.44033(14) 0.57541(8) 0.86292(8) 0.02404(19) Uani 1 1 d . . . . .
C1 C 0.24503(17) 0.42870(9) 0.84700(9) 0.0234(2) Uani 1 1 d . . . . .
C2 C 0.42474(16) 0.31826(9) 0.69036(9) 0.0215(2) Uani 1 1 d . . . . .
C3 C 0.64636(17) 0.32225(9) 0.62694(9) 0.0239(2) Uani 1 1 d . . . . .
H3A H 0.659280 0.404645 0.592838 0.029 Uiso 1 1 calc R U . . .
H3B H 0.759202 0.290663 0.682329 0.029 Uiso 1 1 calc R U . . .
C4 C 0.67791(18) 0.24958(10) 0.53153(10) 0.0264(2) Uani 1 1 d . . . . .
H4 H 0.822191 0.253314 0.490542 0.032 Uiso 1 1 calc R U . . .
C5 C 0.50364(19) 0.29845(11) 0.44554(10) 0.0298(2) Uani 1 1 d . . . . .
H5A H 0.523197 0.251287 0.384143 0.036 Uiso 1 1 calc R U . . .
H5B H 0.514613 0.380549 0.409106 0.036 Uiso 1 1 calc R U . . .
C6 C 0.28252(18) 0.29393(10) 0.50904(10) 0.0281(2) Uani 1 1 d . . . . .
H6 H 0.168585 0.325704 0.453038 0.034 Uiso 1 1 calc R U . . .
C7 C 0.25155(17) 0.36778(9) 0.60362(9) 0.0238(2) Uani 1 1 d . . . . .
H7A H 0.261487 0.450390 0.568739 0.029 Uiso 1 1 calc R U . . .
H7B H 0.107803 0.366019 0.643620 0.029 Uiso 1 1 calc R U . . .
C8 C 0.41142(19) 0.18970(10) 0.74475(10) 0.0275(2) Uani 1 1 d . . . . .
H8A H 0.523996 0.158150 0.800295 0.033 Uiso 1 1 calc R U . . .
H8B H 0.270146 0.185082 0.786904 0.033 Uiso 1 1 calc R U . . .
C9 C 0.4421(2) 0.11667(10) 0.64920(11) 0.0313(3) Uani 1 1 d . . . . .
H9 H 0.431662 0.033248 0.684290 0.038 Uiso 1 1 calc R U . . .
C10 C 0.6625(2) 0.12172(10) 0.58551(11) 0.0320(3) Uani 1 1 d . . . . .
H10A H 0.682703 0.073988 0.524560 0.038 Uiso 1 1 calc R U . . .
H10B H 0.776399 0.089087 0.640078 0.038 Uiso 1 1 calc R U . . .
C11 C 0.2662(2) 0.16644(11) 0.56426(12) 0.0335(3) Uani 1 1 d . . . . .
H11A H 0.282170 0.118556 0.503611 0.040 Uiso 1 1 calc R U . . .
H11B H 0.123682 0.163140 0.605349 0.040 Uiso 1 1 calc R U . . .
C12 C 0.44213(18) 0.66644(10) 0.90533(9) 0.0253(2) Uani 1 1 d . . . . .
H12 H 0.329723 0.690579 0.958758 0.030 Uiso 1 1 calc R U . . .
C13 C 0.61676(18) 0.73320(9) 0.87168(9) 0.0243(2) Uani 1 1 d . . . . .
C14 C 0.79568(19) 0.69679(10) 0.80113(10) 0.0280(2) Uani 1 1 d . . . . .
H14 H 0.805697 0.625701 0.773787 0.034 Uiso 1 1 calc R U . . .
C15 C 0.9584(2) 0.76217(12) 0.77032(11) 0.0337(3) Uani 1 1 d . . . . .
H15 H 1.078480 0.737293 0.721556 0.040 Uiso 1 1 calc R U . . .
C16 C 0.9420(2) 0.86433(11) 0.81213(12) 0.0359(3) Uani 1 1 d . . . . .
C17 C 0.7713(2) 0.90459(11) 0.88246(12) 0.0360(3) Uani 1 1 d . . . . .
H17 H 0.763830 0.974899 0.910838 0.043 Uiso 1 1 calc R U . . .
C18 C 0.6117(2) 0.83746(10) 0.90958(10) 0.0294(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.6894(11) . ?
F1 C16 1.3542(14) . ?
F2 C18 1.3527(14) . ?
N1 C1 1.3361(14) . ?
N1 C2 1.4758(13) . ?
N1 H1N 0.872(16) . ?
N2 C1 1.3608(14) . ?
N2 N3 1.3711(13) . ?
N2 H2N 0.868(17) . ?
N3 C12 1.2801(15) . ?
C2 C7 1.5345(14) . ?
C2 C3 1.5359(14) . ?
C2 C8 1.5383(14) . ?
C3 C4 1.5331(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C10 1.5325(16) . ?
C4 C5 1.5325(16) . ?
C4 H4 1.0000 . ?
C5 C6 1.5342(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.5328(17) . ?
C6 C7 1.5346(15) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5376(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5315(17) . ?
C9 C11 1.5332(18) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.4602(15) . ?
C12 H12 0.9500 . ?
C13 C18 1.3896(16) . ?
C13 C14 1.3988(16) . ?
C14 C15 1.3840(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3792(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(2) . ?
C17 C18 1.3788(18) . ?
C17 H17 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 129.63(9) . . ?
C1 N1 H1N 114.3(10) . . ?
C2 N1 H1N 114.7(10) . . ?
C1 N2 N3 119.76(9) . . ?
C1 N2 H2N 121.6(11) . . ?
N3 N2 H2N 118.6(11) . . ?
C12 N3 N2 116.52(9) . . ?
N1 C1 N2 114.81(10) . . ?
N1 C1 S1 126.94(8) . . ?
N2 C1 S1 118.25(8) . . ?
N1 C2 C7 110.92(8) . . ?
N1 C2 C3 105.22(8) . . ?
C7 C2 C3 109.03(8) . . ?
N1 C2 C8 112.84(9) . . ?
C7 C2 C8 110.22(9) . . ?
C3 C2 C8 108.40(9) . . ?
C4 C3 C2 110.28(8) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C10 C4 C5 109.37(9) . . ?
C10 C4 C3 109.17(9) . . ?
C5 C4 C3 109.70(9) . . ?
C10 C4 H4 109.5 . . ?
C5 C4 H4 109.5 . . ?
C3 C4 H4 109.5 . . ?
C4 C5 C6 109.35(9) . . ?
C4 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
C11 C6 C5 109.46(10) . . ?
C11 C6 C7 109.17(9) . . ?
C5 C6 C7 109.80(9) . . ?
C11 C6 H6 109.5 . . ?
C5 C6 H6 109.5 . . ?
C7 C6 H6 109.5 . . ?
C2 C7 C6 109.52(9) . . ?
C2 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
C2 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C2 109.26(9) . . ?
C9 C8 H8A 109.8 . . ?
C2 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
C2 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C10 C9 C11 109.66(10) . . ?
C10 C9 C8 109.88(10) . . ?
C11 C9 C8 109.13(10) . . ?
C10 C9 H9 109.4 . . ?
C11 C9 H9 109.4 . . ?
C8 C9 H9 109.4 . . ?
C9 C10 C4 109.30(9) . . ?
C9 C10 H10A 109.8 . . ?
C4 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
C4 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
C6 C11 C9 109.75(9) . . ?
C6 C11 H11A 109.7 . . ?
C9 C11 H11A 109.7 . . ?
C6 C11 H11B 109.7 . . ?
C9 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N3 C12 C13 120.07(10) . . ?
N3 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C18 C13 C14 116.70(10) . . ?
C18 C13 C12 120.62(10) . . ?
C14 C13 C12 122.68(10) . . ?
C15 C14 C13 121.38(11) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 118.38(12) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
F1 C16 C17 118.14(12) . . ?
F1 C16 C15 118.70(13) . . ?
C17 C16 C15 123.16(11) . . ?
C16 C17 C18 116.43(11) . . ?
C16 C17 H17 121.8 . . ?
C18 C17 H17 121.8 . . ?
F2 C18 C17 117.88(11) . . ?
F2 C18 C13 118.18(11) . . ?
C17 C18 C13 123.95(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 C12 173.53(10) . . . . ?
C2 N1 C1 N2 -165.14(10) . . . . ?
C2 N1 C1 S1 15.27(17) . . . . ?
N3 N2 C1 N1 8.06(15) . . . . ?
N3 N2 C1 S1 -172.31(8) . . . . ?
C1 N1 C2 C7 55.04(14) . . . . ?
C1 N1 C2 C3 172.80(11) . . . . ?
C1 N1 C2 C8 -69.19(14) . . . . ?
N1 C2 C3 C4 -178.47(8) . . . . ?
C7 C2 C3 C4 -59.43(11) . . . . ?
C8 C2 C3 C4 60.58(11) . . . . ?
C2 C3 C4 C10 -60.48(12) . . . . ?
C2 C3 C4 C5 59.36(12) . . . . ?
C10 C4 C5 C6 60.64(12) . . . . ?
C3 C4 C5 C6 -59.08(12) . . . . ?
C4 C5 C6 C11 -59.95(12) . . . . ?
C4 C5 C6 C7 59.87(12) . . . . ?
N1 C2 C7 C6 175.11(8) . . . . ?
C3 C2 C7 C6 59.70(11) . . . . ?
C8 C2 C7 C6 -59.18(11) . . . . ?
C11 C6 C7 C2 59.56(11) . . . . ?
C5 C6 C7 C2 -60.45(12) . . . . ?
N1 C2 C8 C9 -176.21(9) . . . . ?
C7 C2 C8 C9 59.18(11) . . . . ?
C3 C2 C8 C9 -60.08(11) . . . . ?
C2 C8 C9 C10 60.61(12) . . . . ?
C2 C8 C9 C11 -59.66(12) . . . . ?
C11 C9 C10 C4 59.88(12) . . . . ?
C8 C9 C10 C4 -60.07(13) . . . . ?
C5 C4 C10 C9 -60.55(12) . . . . ?
C3 C4 C10 C9 59.49(12) . . . . ?
C5 C6 C11 C9 59.36(12) . . . . ?
C7 C6 C11 C9 -60.86(12) . . . . ?
C10 C9 C11 C6 -59.42(12) . . . . ?
C8 C9 C11 C6 60.98(12) . . . . ?
N2 N3 C12 C13 -178.70(9) . . . . ?
N3 C12 C13 C18 174.65(11) . . . . ?
N3 C12 C13 C14 -5.51(16) . . . . ?
C18 C13 C14 C15 -0.40(17) . . . . ?
C12 C13 C14 C15 179.76(10) . . . . ?
C13 C14 C15 C16 0.81(18) . . . . ?
C14 C15 C16 F1 179.36(11) . . . . ?
C14 C15 C16 C17 -0.33(19) . . . . ?
F1 C16 C17 C18 179.77(11) . . . . ?
C15 C16 C17 C18 -0.53(19) . . . . ?
C16 C17 C18 F2 -178.88(11) . . . . ?
C16 C17 C18 C13 0.99(18) . . . . ?
C14 C13 C18 F2 179.33(10) . . . . ?
C12 C13 C18 F2 -0.82(16) . . . . ?
C14 C13 C18 C17 -0.54(17) . . . . ?
C12 C13 C18 C17 179.30(11) . . . . ?

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2481863'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Universitat de les Illes Balears
Spain
;
_audit_update_record             
;
2025-08-21 deposited with the CCDC.	2025-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 Cl2 N3 S'
_chemical_formula_sum            'C18 H21 Cl2 N3 S'
_chemical_formula_weight         382.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.28770(10)
_cell_length_b                   11.4798(2)
_cell_length_c                   11.54780(10)
_cell_angle_alpha                71.7340(10)
_cell_angle_beta                 79.2150(10)
_cell_angle_gamma                83.1920(10)
_cell_volume                     899.36(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    20064
_cell_measurement_theta_max      79.5270
_cell_measurement_theta_min      4.0570

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -1 0.0251
0 1 1 0.0311
0 -1 1 0.0455
0 1 -1 0.0455
0 0 1 0.0446
0 0 -1 0.0276
5 2 1 0.1276
-5 -2 0 0.1294
0 1 0 0.0511
0 -1 0 0.0381

_exptl_absorpt_coefficient_mu    4.359
_shelx_estimated_absorpt_T_min   0.375
_shelx_estimated_absorpt_T_max   0.780
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_correction_T_min  0.499

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_reflns_number            24977
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.064
_diffrn_reflns_theta_max         77.277
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3802
_reflns_number_gt                3672
_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       'CrysAlisPRO (OD, 2024)'
_computing_cell_refinement       'CrysAlisPRO (OD, 2024)'
_computing_data_reduction        'CrysAlisPRO (OD, 2024)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2015b)'
_refine_special_details          
;
Owing to poor agreement, five reflections, i.e. (-8 1 0), (2 0 13), (2 3 13),
(2 12 6) and (8 6 3), were omitted from the final cycles of refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0294P)²+0.4292P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3802
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0678
_refine_ls_wR_factor_gt          0.0659
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.07496(5) 0.16140(3) 0.51517(3) 0.03350(10) Uani 1 1 d . . . . .
Cl2 Cl -0.30301(5) 0.64590(3) 0.45165(3) 0.03180(9) Uani 1 1 d . . . . .
S1 S 0.25433(5) 0.38197(3) -0.02326(3) 0.02944(10) Uani 1 1 d . . . . .
N1 N 0.31178(15) 0.28125(10) 0.21418(10) 0.0237(2) Uani 1 1 d . . . . .
H1N H 0.265(2) 0.2770(15) 0.2875(17) 0.030(4) Uiso 1 1 d . . . . .
N2 N 0.05848(15) 0.41621(10) 0.18002(10) 0.0255(2) Uani 1 1 d . . . . .
H2N H -0.010(2) 0.4660(16) 0.1315(17) 0.035(4) Uiso 1 1 d . . . . .
N3 N 0.01188(15) 0.38523(10) 0.30557(9) 0.0232(2) Uani 1 1 d . . . . .
C1 C 0.21175(17) 0.35573(11) 0.13107(11) 0.0227(2) Uani 1 1 d . . . . .
C2 C 0.47311(16) 0.19373(11) 0.19901(11) 0.0207(2) Uani 1 1 d . . . . .
C3 C 0.53098(18) 0.13773(12) 0.32738(11) 0.0258(3) Uani 1 1 d . . . . .
H3A H 0.424114 0.097623 0.387211 0.031 Uiso 1 1 calc R U . . .
H3B H 0.566911 0.203437 0.355846 0.031 Uiso 1 1 calc R U . . .
C4 C 0.69710(18) 0.04263(12) 0.32120(12) 0.0275(3) Uani 1 1 d . . . . .
H4 H 0.734036 0.006163 0.404954 0.033 Uiso 1 1 calc R U . . .
C5 C 0.86337(18) 0.10484(13) 0.22969(13) 0.0295(3) Uani 1 1 d . . . . .
H5A H 0.970158 0.043589 0.225463 0.035 Uiso 1 1 calc R U . . .
H5B H 0.903171 0.169664 0.257728 0.035 Uiso 1 1 calc R U . . .
C6 C 0.80559(17) 0.16163(13) 0.10173(12) 0.0278(3) Uani 1 1 d . . . . .
H6 H 0.913676 0.202557 0.041800 0.033 Uiso 1 1 calc R U . . .
C7 C 0.64082(17) 0.25722(12) 0.10975(12) 0.0252(3) Uani 1 1 d . . . . .
H7A H 0.678075 0.321688 0.139414 0.030 Uiso 1 1 calc R U . . .
H7B H 0.605679 0.296871 0.026857 0.030 Uiso 1 1 calc R U . . .
C8 C 0.41618(17) 0.09088(12) 0.15706(12) 0.0250(3) Uani 1 1 d . . . . .
H8A H 0.376904 0.125986 0.074854 0.030 Uiso 1 1 calc R U . . .
H8B H 0.309047 0.050236 0.216130 0.030 Uiso 1 1 calc R U . . .
C9 C 0.58223(18) -0.00357(12) 0.15034(13) 0.0285(3) Uani 1 1 d . . . . .
H9 H 0.545358 -0.070235 0.122267 0.034 Uiso 1 1 calc R U . . .
C10 C 0.64038(19) -0.05897(12) 0.27807(14) 0.0313(3) Uani 1 1 d . . . . .
H10A H 0.534795 -0.101002 0.337649 0.038 Uiso 1 1 calc R U . . .
H10B H 0.746866 -0.120509 0.274205 0.038 Uiso 1 1 calc R U . . .
C11 C 0.74650(19) 0.06044(13) 0.05861(13) 0.0310(3) Uani 1 1 d . . . . .
H11A H 0.709289 0.096684 -0.024104 0.037 Uiso 1 1 calc R U . . .
H11B H 0.853281 -0.000340 0.052179 0.037 Uiso 1 1 calc R U . . .
C12 C -0.13385(17) 0.43856(11) 0.35167(11) 0.0235(2) Uani 1 1 d . . . . .
H12 H -0.204842 0.500398 0.298916 0.028 Uiso 1 1 calc R U . . .
C13 C -0.19247(16) 0.40455(11) 0.48655(11) 0.0216(2) Uani 1 1 d . . . . .
C14 C -0.17296(17) 0.28490(12) 0.56745(11) 0.0241(2) Uani 1 1 d . . . . .
C15 C -0.2372(2) 0.25732(13) 0.69317(12) 0.0307(3) Uani 1 1 d . . . . .
H15 H -0.220734 0.175751 0.745527 0.037 Uiso 1 1 calc R U . . .
C16 C -0.3254(2) 0.34853(14) 0.74229(12) 0.0352(3) Uani 1 1 d . . . . .
H16 H -0.371070 0.329320 0.828306 0.042 Uiso 1 1 calc R U . . .
C17 C -0.34718(19) 0.46744(13) 0.66685(13) 0.0311(3) Uani 1 1 d . . . . .
H17 H -0.407565 0.530400 0.700408 0.037 Uiso 1 1 calc R U . . .
C18 C -0.28022(17) 0.49390(12) 0.54197(12) 0.0244(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C14 1.7377(13) . ?
Cl2 C18 1.7365(13) . ?
S1 C1 1.6859(12) . ?
N1 C1 1.3353(16) . ?
N1 C2 1.4751(15) . ?
N1 H1N 0.840(18) . ?
N2 N3 1.3657(14) . ?
N2 C1 1.3693(16) . ?
N2 H2N 0.852(18) . ?
N3 C12 1.2746(16) . ?
C2 C8 1.5332(17) . ?
C2 C7 1.5351(17) . ?
C2 C3 1.5365(16) . ?
C3 C4 1.5381(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C10 1.528(2) . ?
C4 C5 1.5323(18) . ?
C4 H4 1.0000 . ?
C5 C6 1.5328(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.531(2) . ?
C6 C7 1.5377(18) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5338(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C11 1.5301(19) . ?
C9 C10 1.530(2) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.4732(16) . ?
C12 H12 0.9500 . ?
C13 C18 1.4047(17) . ?
C13 C14 1.4067(17) . ?
C14 C15 1.3856(18) . ?
C15 C16 1.381(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3811(19) . ?
C17 H17 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 130.30(10) . . ?
C1 N1 H1N 113.6(11) . . ?
C2 N1 H1N 115.5(11) . . ?
N3 N2 C1 118.23(10) . . ?
N3 N2 H2N 122.5(12) . . ?
C1 N2 H2N 118.9(12) . . ?
C12 N3 N2 118.54(10) . . ?
N1 C1 N2 114.50(11) . . ?
N1 C1 S1 127.37(10) . . ?
N2 C1 S1 118.13(9) . . ?
N1 C2 C8 110.52(10) . . ?
N1 C2 C7 112.29(10) . . ?
C8 C2 C7 110.79(10) . . ?
N1 C2 C3 105.96(9) . . ?
C8 C2 C3 108.97(10) . . ?
C7 C2 C3 108.12(10) . . ?
C2 C3 C4 109.71(10) . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C10 C4 C5 109.11(11) . . ?
C10 C4 C3 109.48(11) . . ?
C5 C4 C3 109.80(11) . . ?
C10 C4 H4 109.5 . . ?
C5 C4 H4 109.5 . . ?
C3 C4 H4 109.5 . . ?
C4 C5 C6 109.31(10) . . ?
C4 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
C11 C6 C5 109.39(11) . . ?
C11 C6 C7 109.73(11) . . ?
C5 C6 C7 109.12(11) . . ?
C11 C6 H6 109.5 . . ?
C5 C6 H6 109.5 . . ?
C7 C6 H6 109.5 . . ?
C2 C7 C6 109.52(10) . . ?
C2 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
C2 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C2 C8 C9 109.61(10) . . ?
C2 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C2 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C11 C9 C10 109.42(11) . . ?
C11 C9 C8 109.17(11) . . ?
C10 C9 C8 109.52(11) . . ?
C11 C9 H9 109.6 . . ?
C10 C9 H9 109.6 . . ?
C8 C9 H9 109.6 . . ?
C4 C10 C9 109.72(11) . . ?
C4 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C4 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C9 C11 C6 109.95(11) . . ?
C9 C11 H11A 109.7 . . ?
C6 C11 H11A 109.7 . . ?
C9 C11 H11B 109.7 . . ?
C6 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N3 C12 C13 120.16(11) . . ?
N3 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C18 C13 C14 115.49(11) . . ?
C18 C13 C12 119.92(11) . . ?
C14 C13 C12 124.56(11) . . ?
C15 C14 C13 122.05(12) . . ?
C15 C14 Cl1 115.82(10) . . ?
C13 C14 Cl1 122.08(9) . . ?
C16 C15 C14 119.93(13) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.21(12) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 119.22(12) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C13 123.08(12) . . ?
C17 C18 Cl2 117.56(10) . . ?
C13 C18 Cl2 119.35(10) . . ?

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 C12 -177.93(12) . . . . ?
C2 N1 C1 N2 173.77(12) . . . . ?
C2 N1 C1 S1 -6.3(2) . . . . ?
N3 N2 C1 N1 -7.14(17) . . . . ?
N3 N2 C1 S1 172.94(9) . . . . ?
C1 N1 C2 C8 -63.70(17) . . . . ?
C1 N1 C2 C7 60.57(17) . . . . ?
C1 N1 C2 C3 178.40(13) . . . . ?
N1 C2 C3 C4 178.86(10) . . . . ?
C8 C2 C3 C4 59.93(13) . . . . ?
C7 C2 C3 C4 -60.56(13) . . . . ?
C2 C3 C4 C10 -59.76(14) . . . . ?
C2 C3 C4 C5 60.00(14) . . . . ?
C10 C4 C5 C6 60.73(14) . . . . ?
C3 C4 C5 C6 -59.26(14) . . . . ?
C4 C5 C6 C11 -60.12(14) . . . . ?
C4 C5 C6 C7 59.93(14) . . . . ?
N1 C2 C7 C6 178.09(10) . . . . ?
C8 C2 C7 C6 -57.80(13) . . . . ?
C3 C2 C7 C6 61.55(13) . . . . ?
C11 C6 C7 C2 58.17(13) . . . . ?
C5 C6 C7 C2 -61.67(14) . . . . ?
N1 C2 C8 C9 -176.21(10) . . . . ?
C7 C2 C8 C9 58.67(13) . . . . ?
C3 C2 C8 C9 -60.16(13) . . . . ?
C2 C8 C9 C11 -59.51(14) . . . . ?
C2 C8 C9 C10 60.27(14) . . . . ?
C5 C4 C10 C9 -60.65(13) . . . . ?
C3 C4 C10 C9 59.54(14) . . . . ?
C11 C9 C10 C4 59.77(14) . . . . ?
C8 C9 C10 C4 -59.86(14) . . . . ?
C10 C9 C11 C6 -59.12(14) . . . . ?
C8 C9 C11 C6 60.72(14) . . . . ?
C5 C6 C11 C9 59.44(14) . . . . ?
C7 C6 C11 C9 -60.24(14) . . . . ?
N2 N3 C12 C13 177.85(11) . . . . ?
N3 C12 C13 C18 147.10(12) . . . . ?
N3 C12 C13 C14 -35.14(19) . . . . ?
C18 C13 C14 C15 0.39(18) . . . . ?
C12 C13 C14 C15 -177.46(12) . . . . ?
C18 C13 C14 Cl1 177.84(9) . . . . ?
C12 C13 C14 Cl1 0.00(18) . . . . ?
C13 C14 C15 C16 0.7(2) . . . . ?
Cl1 C14 C15 C16 -176.92(11) . . . . ?
C14 C15 C16 C17 -0.9(2) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C16 C17 C18 C13 1.1(2) . . . . ?
C16 C17 C18 Cl2 -177.62(11) . . . . ?
C14 C13 C18 C17 -1.27(18) . . . . ?
C12 C13 C18 C17 176.68(12) . . . . ?
C14 C13 C18 Cl2 177.39(9) . . . . ?
C12 C13 C18 Cl2 -4.66(16) . . . . ?

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2481861'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Universitat de les Illes Balears
Spain
;
_audit_update_record             
;
2025-08-21 deposited with the CCDC.	2025-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 N4 O2 S'
_chemical_formula_sum            'C18 H22 N4 O2 S'
_chemical_formula_weight         358.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   6.34180(10)
_cell_length_b                   11.5247(3)
_cell_length_c                   12.2090(2)
_cell_angle_alpha                96.592(2)
_cell_angle_beta                 97.243(2)
_cell_angle_gamma                104.197(2)
_cell_volume                     848.26(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    11716
_cell_measurement_theta_min      3.6950
_cell_measurement_theta_max      78.4540

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0229
0 0 -1 0.0229
-2 1 1 0.1030
2 -1 -1 0.1030
0 1 -1 0.0215
0 1 0 0.0060
0 -1 0 0.0240
0 -1 1 0.0195

_exptl_absorpt_coefficient_mu    1.863
_shelx_estimated_absorpt_T_min   0.685
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_reflns_number            18883
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.692
_diffrn_reflns_theta_max         77.336
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3566
_reflns_number_gt                3243
_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       'CrysAlisPRO (OD, 2024)'
_computing_cell_refinement       'CrysAlisPRO (OD, 2024)'
_computing_data_reduction        'CrysAlisPRO (OD, 2024)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2015b)'
_refine_special_details          
;
Owing to poor agreement, two reflections, i.e. (-5 1 12) and (1 11 3), 
were omitted from the final cycles of refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.2982P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3566
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.1009
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.59219(5) 0.61529(3) 0.86634(3) 0.02711(12) Uani 1 1 d . . . . .
O1 O -0.10274(19) 0.08353(12) 0.74584(12) 0.0456(3) Uani 1 1 d . . . . .
O2 O -0.0335(2) -0.02856(13) 0.86892(12) 0.0538(4) Uani 1 1 d . . . . .
N1 N 1.17794(19) 0.60383(11) 0.76821(10) 0.0240(2) Uani 1 1 d . . . . .
H1N H 1.039(3) 0.5657(17) 0.7673(16) 0.034(5) Uiso 1 1 d . . . . .
N2 N 1.21520(19) 0.47604(11) 0.89425(10) 0.0247(3) Uani 1 1 d . . . . .
H2N H 1.293(3) 0.4522(19) 0.9486(18) 0.040(5) Uiso 1 1 d . . . . .
N3 N 0.99456(18) 0.42112(10) 0.86459(10) 0.0231(2) Uani 1 1 d . . . . .
N4 N 0.0217(2) 0.05717(12) 0.81865(12) 0.0337(3) Uani 1 1 d . . . . .
C1 C 1.3152(2) 0.56494(12) 0.83876(11) 0.0221(3) Uani 1 1 d . . . . .
C2 C 1.2269(2) 0.68133(12) 0.68098(11) 0.0213(3) Uani 1 1 d . . . . .
C3 C 1.0003(2) 0.67994(12) 0.61761(11) 0.0230(3) Uani 1 1 d . . . . .
H3A H 0.916888 0.595514 0.587061 0.028 Uiso 1 1 calc R U . . .
H3B H 0.915188 0.713946 0.669545 0.028 Uiso 1 1 calc R U . . .
C4 C 1.0301(2) 0.75515(13) 0.52182(12) 0.0241(3) Uani 1 1 d . . . . .
H4 H 0.882119 0.752800 0.480562 0.029 Uiso 1 1 calc R U . . .
C5 C 1.1621(2) 0.70310(13) 0.44132(12) 0.0267(3) Uani 1 1 d . . . . .
H5A H 1.181441 0.751719 0.379763 0.032 Uiso 1 1 calc R U . . .
H5B H 1.081583 0.618822 0.408572 0.032 Uiso 1 1 calc R U . . .
C6 C 1.3886(2) 0.70559(13) 0.50529(12) 0.0254(3) Uani 1 1 d . . . . .
H6 H 1.475742 0.672004 0.453008 0.030 Uiso 1 1 calc R U . . .
C7 C 1.3579(2) 0.62921(12) 0.60013(12) 0.0230(3) Uani 1 1 d . . . . .
H7A H 1.278336 0.544414 0.568696 0.028 Uiso 1 1 calc R U . . .
H7B H 1.503651 0.629590 0.640530 0.028 Uiso 1 1 calc R U . . .
C8 C 1.3481(2) 0.81306(12) 0.73024(12) 0.0242(3) Uani 1 1 d . . . . .
H8A H 1.493758 0.816402 0.772681 0.029 Uiso 1 1 calc R U . . .
H8B H 1.261929 0.846248 0.782080 0.029 Uiso 1 1 calc R U . . .
C9 C 1.3784(2) 0.88902(12) 0.63470(12) 0.0254(3) Uani 1 1 d . . . . .
H9 H 1.459254 0.974584 0.666520 0.031 Uiso 1 1 calc R U . . .
C10 C 1.1528(2) 0.88625(13) 0.57007(13) 0.0265(3) Uani 1 1 d . . . . .
H10A H 1.066239 0.920991 0.620691 0.032 Uiso 1 1 calc R U . . .
H10B H 1.172717 0.935405 0.508916 0.032 Uiso 1 1 calc R U . . .
C11 C 1.5117(2) 0.83682(13) 0.55503(13) 0.0281(3) Uani 1 1 d . . . . .
H11A H 1.658124 0.839255 0.595980 0.034 Uiso 1 1 calc R U . . .
H11B H 1.534168 0.886302 0.494249 0.034 Uiso 1 1 calc R U . . .
C12 C 0.9148(2) 0.33602(13) 0.91850(12) 0.0249(3) Uani 1 1 d . . . . .
H12 H 1.007960 0.317085 0.977209 0.030 Uiso 1 1 calc R U . . .
C13 C 0.6833(2) 0.26737(13) 0.89147(11) 0.0236(3) Uani 1 1 d . . . . .
C14 C 0.5397(2) 0.28759(13) 0.80305(12) 0.0269(3) Uani 1 1 d . . . . .
H14 H 0.591477 0.348508 0.759339 0.032 Uiso 1 1 calc R U . . .
C15 C 0.3230(2) 0.21912(14) 0.77923(13) 0.0294(3) Uani 1 1 d . . . . .
H15 H 0.224934 0.231898 0.719092 0.035 Uiso 1 1 calc R U . . .
C16 C 0.2517(2) 0.13137(13) 0.84494(12) 0.0271(3) Uani 1 1 d . . . . .
C17 C 0.3876(3) 0.11047(14) 0.93373(13) 0.0314(3) Uani 1 1 d . . . . .
H17 H 0.333672 0.050871 0.978310 0.038 Uiso 1 1 calc R U . . .
C18 C 0.6052(3) 0.17893(14) 0.95607(13) 0.0299(3) Uani 1 1 d . . . . .
H18 H 0.702363 0.165356 1.016206 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.6859(14) . ?
O1 N4 1.2281(19) . ?
O2 N4 1.2244(19) . ?
N1 C1 1.3383(17) . ?
N1 C2 1.4813(16) . ?
N1 H1N 0.88(2) . ?
N2 C1 1.3637(18) . ?
N2 N3 1.3692(16) . ?
N2 H2N 0.88(2) . ?
N3 C12 1.2805(18) . ?
N4 C16 1.4727(18) . ?
C2 C7 1.5299(19) . ?
C2 C8 1.5359(19) . ?
C2 C3 1.5393(17) . ?
C3 C4 1.5371(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C10 1.529(2) . ?
C4 C5 1.531(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.5380(19) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.535(2) . ?
C6 C7 1.5364(19) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5401(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C11 1.531(2) . ?
C9 C10 1.5356(19) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.4628(19) . ?
C12 H12 0.9500 . ?
C13 C18 1.393(2) . ?
C13 C14 1.401(2) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(2) . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 H18 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 129.61(11) . . ?
C1 N1 H1N 112.0(12) . . ?
C2 N1 H1N 117.3(12) . . ?
C1 N2 N3 120.13(11) . . ?
C1 N2 H2N 120.4(14) . . ?
N3 N2 H2N 119.5(13) . . ?
C12 N3 N2 116.22(11) . . ?
O2 N4 O1 123.72(13) . . ?
O2 N4 C16 118.28(14) . . ?
O1 N4 C16 117.98(13) . . ?
N1 C1 N2 114.98(12) . . ?
N1 C1 S1 127.08(11) . . ?
N2 C1 S1 117.94(10) . . ?
N1 C2 C7 111.06(11) . . ?
N1 C2 C8 112.59(11) . . ?
C7 C2 C8 110.34(11) . . ?
N1 C2 C3 105.11(10) . . ?
C7 C2 C3 109.39(11) . . ?
C8 C2 C3 108.15(11) . . ?
C4 C3 C2 109.95(10) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C10 C4 C5 109.56(11) . . ?
C10 C4 C3 109.31(11) . . ?
C5 C4 C3 109.90(11) . . ?
C10 C4 H4 109.4 . . ?
C5 C4 H4 109.4 . . ?
C3 C4 H4 109.4 . . ?
C4 C5 C6 109.23(11) . . ?
C4 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
C11 C6 C7 109.26(12) . . ?
C11 C6 C5 109.20(11) . . ?
C7 C6 C5 109.68(11) . . ?
C11 C6 H6 109.6 . . ?
C7 C6 H6 109.6 . . ?
C5 C6 H6 109.6 . . ?
C2 C7 C6 109.65(11) . . ?
C2 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C2 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C2 C8 C9 109.25(11) . . ?
C2 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
C2 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C11 C9 C10 109.28(12) . . ?
C11 C9 C8 109.37(11) . . ?
C10 C9 C8 110.03(11) . . ?
C11 C9 H9 109.4 . . ?
C10 C9 H9 109.4 . . ?
C8 C9 H9 109.4 . . ?
C4 C10 C9 109.08(11) . . ?
C4 C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
C4 C10 H10B 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C9 C11 C6 109.82(11) . . ?
C9 C11 H11A 109.7 . . ?
C6 C11 H11A 109.7 . . ?
C9 C11 H11B 109.7 . . ?
C6 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N3 C12 C13 121.31(12) . . ?
N3 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C18 C13 C14 119.54(13) . . ?
C18 C13 C12 118.36(12) . . ?
C14 C13 C12 122.10(13) . . ?
C15 C14 C13 120.16(13) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 118.65(13) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C17 C16 C15 122.69(13) . . ?
C17 C16 N4 118.61(13) . . ?
C15 C16 N4 118.70(13) . . ?
C16 C17 C18 118.10(14) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C17 C18 C13 120.85(14) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?

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
C1 N2 N3 C12 177.91(13) . . . . ?
C2 N1 C1 N2 -167.86(13) . . . . ?
C2 N1 C1 S1 13.1(2) . . . . ?
N3 N2 C1 N1 9.35(19) . . . . ?
N3 N2 C1 S1 -171.50(10) . . . . ?
C1 N1 C2 C7 54.38(18) . . . . ?
C1 N1 C2 C8 -69.93(18) . . . . ?
C1 N1 C2 C3 172.57(13) . . . . ?
N1 C2 C3 C4 -178.39(11) . . . . ?
C7 C2 C3 C4 -59.07(14) . . . . ?
C8 C2 C3 C4 61.13(14) . . . . ?
C2 C3 C4 C10 -61.06(15) . . . . ?
C2 C3 C4 C5 59.21(15) . . . . ?
C10 C4 C5 C6 60.76(14) . . . . ?
C3 C4 C5 C6 -59.36(14) . . . . ?
C4 C5 C6 C11 -59.76(15) . . . . ?
C4 C5 C6 C7 59.94(15) . . . . ?
N1 C2 C7 C6 175.18(11) . . . . ?
C8 C2 C7 C6 -59.25(14) . . . . ?
C3 C2 C7 C6 59.61(14) . . . . ?
C11 C6 C7 C2 59.30(14) . . . . ?
C5 C6 C7 C2 -60.37(15) . . . . ?
N1 C2 C8 C9 -176.15(10) . . . . ?
C7 C2 C8 C9 59.15(14) . . . . ?
C3 C2 C8 C9 -60.47(14) . . . . ?
C2 C8 C9 C11 -59.42(14) . . . . ?
C2 C8 C9 C10 60.63(15) . . . . ?
C5 C4 C10 C9 -60.96(14) . . . . ?
C3 C4 C10 C9 59.52(15) . . . . ?
C11 C9 C10 C4 60.36(14) . . . . ?
C8 C9 C10 C4 -59.74(15) . . . . ?
C10 C9 C11 C6 -60.04(14) . . . . ?
C8 C9 C11 C6 60.47(14) . . . . ?
C7 C6 C11 C9 -60.27(14) . . . . ?
C5 C6 C11 C9 59.70(15) . . . . ?
N2 N3 C12 C13 -177.58(12) . . . . ?
N3 C12 C13 C18 -177.69(14) . . . . ?
N3 C12 C13 C14 2.6(2) . . . . ?
C18 C13 C14 C15 -0.8(2) . . . . ?
C12 C13 C14 C15 178.86(14) . . . . ?
C13 C14 C15 C16 0.4(2) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C14 C15 C16 N4 -179.14(13) . . . . ?
O2 N4 C16 C17 -7.7(2) . . . . ?
O1 N4 C16 C17 173.74(15) . . . . ?
O2 N4 C16 C15 172.15(15) . . . . ?
O1 N4 C16 C15 -6.4(2) . . . . ?
C15 C16 C17 C18 -1.3(2) . . . . ?
N4 C16 C17 C18 178.51(14) . . . . ?
C16 C17 C18 C13 0.8(2) . . . . ?
C14 C13 C18 C17 0.2(2) . . . . ?
C12 C13 C18 C17 -179.51(14) . . . . ?

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.048

