# 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_cu_AD_05_11_Cu_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2402535'
loop_
_audit_author_name
_audit_author_address
'Ashutosh Bedekar'
;Department of Chemistry, M S University of Baroda, Vadodara
India
;
_audit_update_record             
;
2024-11-14 deposited with the CCDC.	2025-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H20 N2 S'
_chemical_formula_sum            'C17 H20 N2 S'
_chemical_formula_weight         284.41

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

_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'

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

_cell_length_a                   10.2178(2)
_cell_length_b                   10.2178(2)
_cell_length_c                   13.0003(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1175.43(6)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      5.00
_cell_measurement_theta_max      78.26

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.750
_shelx_estimated_absorpt_T_min   0.792
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6375
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_process_details   'SADABS (BRUKER, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            36394
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.998
_diffrn_reflns_theta_max         78.820
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             3228
_reflns_number_gt                3036
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_max     0.927
_reflns_Friedel_fraction_full    0.957

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion 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)+(0.0177P)²+0.3307P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.010(17)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3228
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0631
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.11727(6) 0.47033(6) 0.63127(4) 0.02565(14) Uani 1 1 d . . . . .
N1 N 0.3107(2) 0.6732(2) 0.49524(15) 0.0247(4) Uani 1 1 d . . . . .
H1N H 0.372(3) 0.689(3) 0.449(2) 0.013(6) Uiso 1 1 d . . . . .
N2 N 0.2839(2) 0.4411(2) 0.48499(15) 0.0234(4) Uani 1 1 d . . . . .
H2N H 0.346(3) 0.479(3) 0.435(2) 0.032(8) Uiso 1 1 d . . . . .
C1 C 0.2766(3) 0.7927(3) 0.51991(18) 0.0261(5) Uani 1 1 d . . . . .
H1 H 0.208443 0.760420 0.581276 0.031 Uiso 1 1 calc R U . . .
C2 C 0.1942(3) 0.8144(2) 0.43007(17) 0.0215(5) Uani 1 1 d . . . . .
C3 C 0.2702(3) 0.8800(3) 0.33899(19) 0.0260(5) Uani 1 1 d . . . . .
H3 H 0.374268 0.910632 0.332743 0.031 Uiso 1 1 calc R U . . .
C4 C 0.1957(3) 0.9012(3) 0.25730(19) 0.0348(6) Uani 1 1 d . . . . .
H4 H 0.248549 0.945278 0.195225 0.042 Uiso 1 1 calc R U . . .
C5 C 0.0452(3) 0.8584(3) 0.2658(2) 0.0366(6) Uani 1 1 d . . . . .
H5 H -0.005027 0.874867 0.210138 0.044 Uiso 1 1 calc R U . . .
C6 C -0.0330(3) 0.7915(3) 0.3556(2) 0.0361(6) Uani 1 1 d . . . . .
H6 H -0.137273 0.760503 0.361227 0.043 Uiso 1 1 calc R U . . .
C7 C 0.0424(3) 0.7701(3) 0.4373(2) 0.0282(5) Uani 1 1 d . . . . .
H7 H -0.011094 0.724407 0.498946 0.034 Uiso 1 1 calc R U . . .
C8 C 0.4230(4) 0.9366(3) 0.5474(2) 0.0420(7) Uani 1 1 d . . . . .
H8A H 0.496478 0.961631 0.491764 0.063 Uiso 1 1 calc R U . . .
H8B H 0.463976 0.920645 0.611289 0.063 Uiso 1 1 calc R U . . .
H8C H 0.402469 1.019813 0.556758 0.063 Uiso 1 1 calc R U . . .
C9 C 0.2437(2) 0.5326(2) 0.53194(16) 0.0205(4) Uani 1 1 d . . . . .
C10 C 0.2396(3) 0.2867(3) 0.51488(17) 0.0232(5) Uani 1 1 d . . . . .
H10 H 0.138259 0.240573 0.548720 0.028 Uiso 1 1 calc R U . . .
C11 C 0.3499(3) 0.2796(3) 0.58946(17) 0.0235(5) Uani 1 1 d . . . . .
C12 C 0.2971(3) 0.1917(3) 0.67757(19) 0.0325(6) Uani 1 1 d . . . . .
H12 H 0.192283 0.142193 0.693298 0.039 Uiso 1 1 calc R U . . .
C13 C 0.3950(3) 0.1750(3) 0.7431(2) 0.0400(7) Uani 1 1 d . . . . .
H13 H 0.357006 0.113335 0.802622 0.048 Uiso 1 1 calc R U . . .
C14 C 0.5477(3) 0.2481(3) 0.7215(2) 0.0355(6) Uani 1 1 d . . . . .
H14 H 0.614993 0.236183 0.765817 0.043 Uiso 1 1 calc R U . . .
C15 C 0.6024(3) 0.3384(3) 0.6352(2) 0.0348(6) Uani 1 1 d . . . . .
H15 H 0.707644 0.390023 0.620808 0.042 Uiso 1 1 calc R U . . .
C16 C 0.5042(3) 0.3541(3) 0.56967(19) 0.0294(5) Uani 1 1 d . . . . .
H16 H 0.542753 0.416509 0.510495 0.035 Uiso 1 1 calc R U . . .
C17 C 0.2249(3) 0.1979(3) 0.41703(19) 0.0293(5) Uani 1 1 d . . . . .
H17A H 0.149944 0.200706 0.371417 0.044 Uiso 1 1 calc R U . . .
H17B H 0.192389 0.092825 0.434839 0.044 Uiso 1 1 calc R U . . .
H17C H 0.322825 0.243165 0.381971 0.044 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 C9 1.709(2) . ?
N1 C9 1.333(3) . ?
N1 C1 1.463(3) . ?
N1 H1N 0.83(3) . ?
N2 C9 1.342(3) . ?
N2 C10 1.459(3) . ?
N2 H2N 0.85(3) . ?
C1 C2 1.519(3) . ?
C1 C8 1.525(4) . ?
C1 H1 1.0000 . ?
C2 C7 1.385(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 C11 1.516(3) . ?
C10 C17 1.526(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.388(3) . ?
C11 C16 1.389(3) . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
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
C9 N1 C1 127.8(2) . . ?
C9 N1 H1N 114.1(17) . . ?
C1 N1 H1N 117.7(17) . . ?
C9 N2 C10 126.47(19) . . ?
C9 N2 H2N 116(2) . . ?
C10 N2 H2N 117(2) . . ?
N1 C1 C2 109.51(18) . . ?
N1 C1 C8 109.1(2) . . ?
C2 C1 C8 112.8(2) . . ?
N1 C1 H1 108.4 . . ?
C2 C1 H1 108.4 . . ?
C8 C1 H1 108.4 . . ?
C7 C2 C3 118.7(2) . . ?
C7 C2 C1 120.8(2) . . ?
C3 C2 C1 120.5(2) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 119.5(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C6 120.9(2) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 N2 114.7(2) . . ?
N1 C9 S1 123.84(18) . . ?
N2 C9 S1 121.50(17) . . ?
N2 C10 C11 112.70(19) . . ?
N2 C10 C17 107.81(19) . . ?
C11 C10 C17 111.07(19) . . ?
N2 C10 H10 108.4 . . ?
C11 C10 H10 108.4 . . ?
C17 C10 H10 108.4 . . ?
C12 C11 C16 118.4(2) . . ?
C12 C11 C10 120.1(2) . . ?
C16 C11 C10 121.5(2) . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 -105.9(3) . . . . ?
C9 N1 C1 C8 130.2(3) . . . . ?
N1 C1 C2 C7 109.2(2) . . . . ?
C8 C1 C2 C7 -129.1(3) . . . . ?
N1 C1 C2 C3 -71.1(3) . . . . ?
C8 C1 C2 C3 50.6(3) . . . . ?
C7 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C4 -179.4(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C4 C5 C6 C7 1.0(4) . . . . ?
C3 C2 C7 C6 -0.5(3) . . . . ?
C1 C2 C7 C6 179.2(2) . . . . ?
C5 C6 C7 C2 -0.1(4) . . . . ?
C1 N1 C9 N2 171.1(2) . . . . ?
C1 N1 C9 S1 -9.4(3) . . . . ?
C10 N2 C9 N1 174.0(2) . . . . ?
C10 N2 C9 S1 -5.5(3) . . . . ?
C9 N2 C10 C11 -90.6(3) . . . . ?
C9 N2 C10 C17 146.5(2) . . . . ?
N2 C10 C11 C12 132.2(2) . . . . ?
C17 C10 C11 C12 -106.7(2) . . . . ?
N2 C10 C11 C16 -50.8(3) . . . . ?
C17 C10 C11 C16 70.3(3) . . . . ?
C16 C11 C12 C13 -1.7(4) . . . . ?
C10 C11 C12 C13 175.3(2) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C15 C16 C11 0.0(4) . . . . ?
C12 C11 C16 C15 1.3(4) . . . . ?
C10 C11 C16 C15 -175.7(2) . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.034



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_AD_06_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2403604'
loop_
_audit_author_name
_audit_author_address
'Ashutosh Bedekar'
;Department of Chemistry, M S University of Baroda, Vadodara
India
;
_audit_update_record             
;
2024-11-18 deposited with the CCDC.	2025-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H20 N2 S'
_chemical_formula_sum            'C17 H20 N2 S'
_chemical_formula_weight         284.41

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

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

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

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

_cell_length_a                   12.9267(11)
_cell_length_b                   12.7298(11)
_cell_length_c                   9.3576(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.901(2)
_cell_angle_gamma                90
_cell_volume                     1539.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      4.88
_cell_measurement_theta_max      72.47

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.782
_shelx_estimated_absorpt_T_min   0.815
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6639
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            32594
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.876
_diffrn_reflns_theta_max         72.692
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3011
_reflns_number_gt                2912
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0378P)²+0.8087P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3011
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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 0.63947(2) 0.41402(2) 0.58059(3) 0.01711(11) Uani 1 1 d . . . . .
N1' N 0.52311(8) 0.36938(8) 0.35630(11) 0.0171(2) Uani 1 1 d . . . . .
H2 H 0.4908(13) 0.4212(13) 0.3873(19) 0.025(4) Uiso 1 1 d . . . . .
N1 N 0.66723(8) 0.26367(8) 0.38300(12) 0.0176(2) Uani 1 1 d . . . . .
H8 H 0.6477(13) 0.2321(13) 0.3057(19) 0.026(4) Uiso 1 1 d . . . . .
C1' C 0.47579(9) 0.31661(9) 0.23193(13) 0.0165(3) Uani 1 1 d . . . . .
H1' H 0.528386 0.268665 0.189611 0.020 Uiso 1 1 calc R U . . .
C1 C 0.76738(10) 0.23279(10) 0.44715(14) 0.0190(3) Uani 1 1 d . . . . .
H1 H 0.770903 0.263475 0.545481 0.023 Uiso 1 1 calc R U . . .
C2' C 0.38301(9) 0.25127(9) 0.27507(13) 0.0162(2) Uani 1 1 d . . . . .
C2 C 0.85680(10) 0.27919(10) 0.36328(14) 0.0198(3) Uani 1 1 d . . . . .
C3' C 0.30715(10) 0.29358(10) 0.36247(14) 0.0222(3) Uani 1 1 d . . . . .
H3' H 0.314219 0.363280 0.397554 0.027 Uiso 1 1 calc R U . . .
C3 C 0.88681(11) 0.38284(11) 0.38950(15) 0.0245(3) Uani 1 1 d . . . . .
H3 H 0.851065 0.423136 0.458462 0.029 Uiso 1 1 calc R U . . .
C4' C 0.22141(11) 0.23417(11) 0.39833(16) 0.0279(3) Uani 1 1 d . . . . .
H4' H 0.170305 0.263217 0.458560 0.033 Uiso 1 1 calc R U . . .
C4 C 0.96815(12) 0.42786(12) 0.31623(17) 0.0315(3) Uani 1 1 d . . . . .
H4 H 0.987872 0.498420 0.335417 0.038 Uiso 1 1 calc R U . . .
C5 C 1.02073(11) 0.36969(14) 0.21478(17) 0.0355(4) Uani 1 1 d . . . . .
H5 H 1.076313 0.400265 0.164200 0.043 Uiso 1 1 calc R U . . .
C5' C 0.20984(11) 0.13243(11) 0.34667(16) 0.0263(3) Uani 1 1 d . . . . .
H5' H 0.150788 0.092159 0.370925 0.032 Uiso 1 1 calc R U . . .
C6' C 0.28468(11) 0.09009(10) 0.25979(15) 0.0236(3) Uani 1 1 d . . . . .
H6' H 0.276914 0.020636 0.224050 0.028 Uiso 1 1 calc R U . . .
C6 C 0.99146(12) 0.26682(14) 0.18800(17) 0.0360(4) Uani 1 1 d . . . . .
H6 H 1.027234 0.226751 0.118819 0.043 Uiso 1 1 calc R U . . .
C7 C 0.91036(11) 0.22194(12) 0.26139(15) 0.0275(3) Uani 1 1 d . . . . .
H7 H 0.891066 0.151289 0.242004 0.033 Uiso 1 1 calc R U . . .
C7' C 0.37135(10) 0.14893(10) 0.22456(13) 0.0198(3) Uani 1 1 d . . . . .
H7' H 0.422890 0.119136 0.165710 0.024 Uiso 1 1 calc R U . . .
C8' C 0.44693(11) 0.40006(11) 0.12098(14) 0.0230(3) Uani 1 1 d . . . . .
H8'A H 0.509115 0.438863 0.093957 0.035 Uiso 1 1 calc R U . . .
H8'B H 0.396589 0.448796 0.161570 0.035 Uiso 1 1 calc R U . . .
H8'C H 0.416578 0.366071 0.036222 0.035 Uiso 1 1 calc R U . . .
C9 C 0.60871(9) 0.34333(9) 0.42909(12) 0.0154(2) Uani 1 1 d . . . . .
C8 C 0.77070(11) 0.11348(10) 0.46307(16) 0.0263(3) Uani 1 1 d . . . . .
H8A H 0.762428 0.080702 0.368824 0.039 Uiso 1 1 calc R U . . .
H8B H 0.714503 0.090605 0.524895 0.039 Uiso 1 1 calc R U . . .
H8C H 0.837289 0.092557 0.505713 0.039 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 C9 1.7205(12) . ?
N1' C9 1.3322(16) . ?
N1' C1' 1.4689(15) . ?
N1' H2 0.835(18) . ?
N1 C9 1.3405(16) . ?
N1 C1 1.4719(16) . ?
N1 H8 0.862(18) . ?
C1' C2' 1.5192(17) . ?
C1' C8' 1.5276(17) . ?
C1' H1' 1.0000 . ?
C1 C2 1.5263(18) . ?
C1 C8 1.5265(17) . ?
C1 H1 1.0000 . ?
C2' C7' 1.3932(17) . ?
C2' C3' 1.3950(18) . ?
C2 C7 1.3930(19) . ?
C2 C3 1.3960(19) . ?
C3' C4' 1.3872(19) . ?
C3' H3' 0.9500 . ?
C3 C4 1.388(2) . ?
C3 H3 0.9500 . ?
C4' C5' 1.390(2) . ?
C4' H4' 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C5' C6' 1.383(2) . ?
C5' H5' 0.9500 . ?
C6' C7' 1.3916(19) . ?
C6' H6' 0.9500 . ?
C6 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7' H7' 0.9500 . ?
C8' H8'A 0.9800 . ?
C8' H8'B 0.9800 . ?
C8' H8'C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
C9 N1' C1' 128.57(11) . . ?
C9 N1' H2 115.8(12) . . ?
C1' N1' H2 115.6(12) . . ?
C9 N1 C1 124.61(11) . . ?
C9 N1 H8 117.6(11) . . ?
C1 N1 H8 117.6(11) . . ?
N1' C1' C2' 111.13(10) . . ?
N1' C1' C8' 108.34(10) . . ?
C2' C1' C8' 112.08(10) . . ?
N1' C1' H1' 108.4 . . ?
C2' C1' H1' 108.4 . . ?
C8' C1' H1' 108.4 . . ?
N1 C1 C2 110.81(10) . . ?
N1 C1 C8 109.19(11) . . ?
C2 C1 C8 114.51(11) . . ?
N1 C1 H1 107.3 . . ?
C2 C1 H1 107.3 . . ?
C8 C1 H1 107.3 . . ?
C7' C2' C3' 119.11(12) . . ?
C7' C2' C1' 120.23(11) . . ?
C3' C2' C1' 120.64(11) . . ?
C7 C2 C3 118.36(13) . . ?
C7 C2 C1 122.55(12) . . ?
C3 C2 C1 119.08(12) . . ?
C4' C3' C2' 120.20(12) . . ?
C4' C3' H3' 119.9 . . ?
C2' C3' H3' 119.9 . . ?
C4 C3 C2 120.93(13) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3' C4' C5' 120.39(13) . . ?
C3' C4' H4' 119.8 . . ?
C5' C4' H4' 119.8 . . ?
C3 C4 C5 119.98(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.49(14) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C6' C5' C4' 119.69(13) . . ?
C6' C5' H5' 120.2 . . ?
C4' C5' H5' 120.2 . . ?
C5' C6' C7' 120.18(12) . . ?
C5' C6' H6' 119.9 . . ?
C7' C6' H6' 119.9 . . ?
C5 C6 C7 120.46(14) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 120.77(14) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
C6' C7' C2' 120.41(12) . . ?
C6' C7' H7' 119.8 . . ?
C2' C7' H7' 119.8 . . ?
C1' C8' H8'A 109.5 . . ?
C1' C8' H8'B 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
C1' C8' H8'C 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?
N1' C9 N1 119.49(11) . . ?
N1' C9 S1 118.06(9) . . ?
N1 C9 S1 122.45(9) . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
C9 N1' C1' C2' 102.34(14) . . . . ?
C9 N1' C1' C8' -134.11(13) . . . . ?
C9 N1 C1 C2 -97.97(14) . . . . ?
C9 N1 C1 C8 135.00(12) . . . . ?
N1' C1' C2' C7' -133.66(12) . . . . ?
C8' C1' C2' C7' 104.95(13) . . . . ?
N1' C1' C2' C3' 48.00(15) . . . . ?
C8' C1' C2' C3' -73.39(15) . . . . ?
N1 C1 C2 C7 -98.23(14) . . . . ?
C8 C1 C2 C7 25.80(18) . . . . ?
N1 C1 C2 C3 82.03(14) . . . . ?
C8 C1 C2 C3 -153.93(12) . . . . ?
C7' C2' C3' C4' 0.02(19) . . . . ?
C1' C2' C3' C4' 178.37(12) . . . . ?
C7 C2 C3 C4 -0.1(2) . . . . ?
C1 C2 C3 C4 179.60(12) . . . . ?
C2' C3' C4' C5' -0.5(2) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C3' C4' C5' C6' 0.4(2) . . . . ?
C4' C5' C6' C7' 0.2(2) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C2 0.0(2) . . . . ?
C3 C2 C7 C6 0.0(2) . . . . ?
C1 C2 C7 C6 -179.70(13) . . . . ?
C5' C6' C7' C2' -0.7(2) . . . . ?
C3' C2' C7' C6' 0.60(18) . . . . ?
C1' C2' C7' C6' -177.76(11) . . . . ?
C1' N1' C9 N1 5.24(18) . . . . ?
C1' N1' C9 S1 -174.51(9) . . . . ?
C1 N1 C9 N1' 174.93(11) . . . . ?
C1 N1 C9 S1 -5.32(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1' H2 S1 0.835(18) 2.709(18) 3.5224(11) 164.8(15) 3_666 yes
N1 H8 S1 0.862(18) 2.811(18) 3.6360(11) 160.8(14) 4_565 yes
C1' H1' S1 1.00 2.93 3.8981(12) 164.5 4_565 yes
C1 H1 S1 1.00 2.59 3.1114(13) 112.7 . yes
C8' H8'B S1 0.98 3.02 3.8399(14) 141.9 3_666 yes

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.044



