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

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

data_2090619GTLI
_database_code_depnum_ccdc_archive 'CCDC 1959788'
loop_
_audit_author_name
_audit_author_address
'Tao Guo'
;Henan University of Technology
China
;
_audit_update_record             
;
2019-10-17 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H13 Cl N3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         374.85

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   15.1373(14)
_cell_length_b                   14.4119(13)
_cell_length_c                   16.4702(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3593.1(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9606
_cell_measurement_theta_min      5.0164
_cell_measurement_theta_max      68.2568
_cell_measurement_temperature    242.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1544

_exptl_absorpt_coefficient_mu    3.034
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;
;

_diffrn_ambient_temperature      242.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'cu k\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'd8 venture'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            37080
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_theta_min         5.02
_diffrn_reflns_theta_max         68.29
_diffrn_reflns_theta_full        68.29
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             3275
_reflns_number_gt                3208
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0753
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_number_reflns         3275
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+1.4958P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.35938(2) 0.81937(3) 0.40574(2) 0.03464(11) Uani d . . . 1 . .
S S1 0.26509(2) 0.64374(2) 0.52679(2) 0.02393(10) Uani d . . . 1 . .
N N1 0.14040(7) 0.76758(8) 0.58379(6) 0.0230(2) Uani d . . . 1 . .
N N2 0.08448(7) 0.70129(8) 0.69545(7) 0.0259(2) Uani d . . . 1 . .
N N3 0.46563(8) 0.69371(9) 0.67187(8) 0.0299(3) Uani d . . . 1 . .
H H14 0.4946(12) 0.6868(13) 0.7152(13) 0.043(5) Uiso d . . . 1 . .
C C1 0.55828(9) 0.88798(10) 0.55421(9) 0.0330(3) Uani d . . . 1 . .
H H1 0.602776 0.933473 0.554171 0.04 Uiso calc U . R 1 . .
C C2 0.55351(9) 0.82633(10) 0.61753(9) 0.0314(3) Uani d . . . 1 . .
H H13 0.594638 0.827826 0.660274 0.038 Uiso calc U . R 1 . .
C C3 0.48512(8) 0.76123(9) 0.61598(8) 0.0265(3) Uani d . . . 1 . .
C C4 0.42134(8) 0.75644(9) 0.55288(8) 0.0230(3) Uani d . . . 1 . .
C C5 0.36224(8) 0.68269(9) 0.57522(8) 0.0231(3) Uani d . . . 1 . .
C C6 0.18330(8) 0.68262(9) 0.59322(7) 0.0217(3) Uani d . . . 1 . .
C C7 0.14723(8) 0.64406(9) 0.66236(7) 0.0225(3) Uani d . . . 1 . .
C C8 0.17063(8) 0.55625(9) 0.70297(8) 0.0239(3) Uani d . . . 1 . .
C C9 0.18004(9) 0.47318(10) 0.66080(9) 0.0304(3) Uani d . . . 1 . .
H H5 0.171287 0.471865 0.60431 0.036 Uiso calc U . R 1 . .
C C10 0.20228(10) 0.39219(10) 0.70168(10) 0.0361(3) Uani d . . . 1 . .
H H6 0.207699 0.336146 0.672909 0.043 Uiso calc U . R 1 . .
C C11 0.21651(10) 0.39380(11) 0.78483(10) 0.0385(4) Uani d . . . 1 . .
H H2 0.232318 0.339113 0.812333 0.046 Uiso calc U . R 1 . .
C C12 0.43113(9) 0.82016(9) 0.48886(8) 0.0257(3) Uani d . . . 1 . .
C C13 0.49801(9) 0.88449(10) 0.48942(9) 0.0302(3) Uani d . . . 1 . .
H H3 0.503521 0.926556 0.446098 0.036 Uiso calc U . R 1 . .
C C14 0.15080(9) 0.83587(10) 0.52636(9) 0.0297(3) Uani d . . . 1 . .
H H11 0.19169 0.828845 0.483845 0.036 Uiso calc U . R 1 . .
C C15 0.10091(10) 0.91345(11) 0.53235(10) 0.0369(3) Uani d . . . 1 . .
H H10 0.107723 0.961161 0.493943 0.044 Uiso calc U . R 1 . .
C C16 0.03859(10) 0.92361(10) 0.59575(10) 0.0373(3) Uani d . . . 1 . .
H H4 0.004176 0.977796 0.598728 0.045 Uiso calc U . R 1 . .
C C17 0.02788(10) 0.85604(10) 0.65234(9) 0.0326(3) Uani d . . . 1 . .
H H9 -0.013912 0.862711 0.694145 0.039 Uiso calc U . R 1 . .
C C18 0.08082(8) 0.77548(9) 0.64715(8) 0.0255(3) Uani d . . . 1 . .
C C19 0.20738(11) 0.47603(12) 0.82717(9) 0.0411(4) Uani d . . . 1 . .
H H7 0.217187 0.477185 0.883515 0.049 Uiso calc U . R 1 . .
C C20 0.18387(10) 0.55666(11) 0.78702(8) 0.0333(3) Uani d . . . 1 . .
H H8 0.176752 0.612064 0.816411 0.04 Uiso calc U . R 1 . .
C C21 0.39262(9) 0.64681(9) 0.64740(8) 0.0273(3) Uani d . . . 1 . .
H H12 0.366623 0.597125 0.675609 0.033 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C12 . 1.7475(14) ?
S1 C6 . 1.7446(13) ?
S1 C5 . 1.7646(13) ?
N1 C14 . 1.3741(18) ?
N1 C18 . 1.3840(17) ?
N1 C6 . 1.3947(17) ?
N2 C18 . 1.3338(18) ?
N2 C7 . 1.3710(17) ?
N3 C21 . 1.3568(19) ?
N3 C3 . 1.3716(19) ?
N3 H14 . 0.84(2) ?
C1 C2 . 1.372(2) ?
C1 C13 . 1.405(2) ?
C1 H1 . 0.94 ?
C2 C3 . 1.397(2) ?
C2 H13 . 0.94 ?
C3 C4 . 1.4203(18) ?
C4 C12 . 1.4061(19) ?
C4 C5 . 1.4371(18) ?
C5 C21 . 1.3755(19) ?
C6 C7 . 1.3798(18) ?
C7 C8 . 1.4746(18) ?
C8 C9 . 1.3914(19) ?
C8 C20 . 1.3987(19) ?
C9 C10 . 1.389(2) ?
C9 H5 . 0.94 ?
C10 C11 . 1.387(2) ?
C10 H6 . 0.94 ?
C11 C19 . 1.382(2) ?
C11 H2 . 0.94 ?
C12 C13 . 1.373(2) ?
C13 H3 . 0.94 ?
C14 C15 . 1.353(2) ?
C14 H11 . 0.94 ?
C15 C16 . 1.415(2) ?
C15 H10 . 0.94 ?
C16 C17 . 1.358(2) ?
C16 H4 . 0.94 ?
C17 C18 . 1.4133(19) ?
C17 H9 . 0.94 ?
C19 C20 . 1.384(2) ?
C19 H7 . 0.94 ?
C20 H8 . 0.94 ?
C21 H12 . 0.94 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 S1 C5 . . 101.87(6) ?
C14 N1 C18 . . 122.33(12) ?
C14 N1 C6 . . 130.70(11) ?
C18 N1 C6 . . 106.96(10) ?
C18 N2 C7 . . 105.90(11) ?
C21 N3 C3 . . 109.22(12) ?
C21 N3 H14 . . 128.0(13) ?
C3 N3 H14 . . 122.7(13) ?
C2 C1 C13 . . 121.34(13) ?
C2 C1 H1 . . 119.3 ?
C13 C1 H1 . . 119.3 ?
C1 C2 C3 . . 117.38(13) ?
C1 C2 H13 . . 121.3 ?
C3 C2 H13 . . 121.3 ?
N3 C3 C2 . . 128.57(13) ?
N3 C3 C4 . . 108.08(12) ?
C2 C3 C4 . . 123.34(13) ?
C12 C4 C3 . . 116.44(12) ?
C12 C4 C5 . . 137.78(12) ?
C3 C4 C5 . . 105.77(11) ?
C21 C5 C4 . . 106.92(11) ?
C21 C5 S1 . . 123.34(10) ?
C4 C5 S1 . . 129.67(10) ?
C7 C6 N1 . . 105.15(11) ?
C7 C6 S1 . . 131.99(10) ?
N1 C6 S1 . . 122.86(9) ?
N2 C7 C6 . . 111.10(11) ?
N2 C7 C8 . . 120.16(11) ?
C6 C7 C8 . . 128.68(12) ?
C9 C8 C20 . . 118.88(13) ?
C9 C8 C7 . . 122.45(11) ?
C20 C8 C7 . . 118.67(12) ?
C10 C9 C8 . . 120.39(13) ?
C10 C9 H5 . . 119.8 ?
C8 C9 H5 . . 119.8 ?
C11 C10 C9 . . 120.16(14) ?
C11 C10 H6 . . 119.9 ?
C9 C10 H6 . . 119.9 ?
C19 C11 C10 . . 119.82(14) ?
C19 C11 H2 . . 120.1 ?
C10 C11 H2 . . 120.1 ?
C13 C12 C4 . . 120.91(13) ?
C13 C12 Cl1 . . 117.90(11) ?
C4 C12 Cl1 . . 121.18(10) ?
C12 C13 C1 . . 120.54(13) ?
C12 C13 H3 . . 119.7 ?
C1 C13 H3 . . 119.7 ?
C15 C14 N1 . . 118.54(13) ?
C15 C14 H11 . . 120.7 ?
N1 C14 H11 . . 120.7 ?
C14 C15 C16 . . 120.77(14) ?
C14 C15 H10 . . 119.6 ?
C16 C15 H10 . . 119.6 ?
C17 C16 C15 . . 120.80(14) ?
C17 C16 H4 . . 119.6 ?
C15 C16 H4 . . 119.6 ?
C16 C17 C18 . . 118.69(14) ?
C16 C17 H9 . . 120.7 ?
C18 C17 H9 . . 120.7 ?
N2 C18 N1 . . 110.90(11) ?
N2 C18 C17 . . 130.25(12) ?
N1 C18 C17 . . 118.86(12) ?
C11 C19 C20 . . 120.32(14) ?
C11 C19 H7 . . 119.8 ?
C20 C19 H7 . . 119.8 ?
C19 C20 C8 . . 120.42(14) ?
C19 C20 H8 . . 119.8 ?
C8 C20 H8 . . 119.8 ?
N3 C21 C5 . . 109.99(12) ?
N3 C21 H12 . . 125.0 ?
C5 C21 H12 . . 125.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 C1 C2 C3 . . . . -1.4(2) ?
C21 N3 C3 C2 . . . . 178.86(13) ?
C21 N3 C3 C4 . . . . -0.23(15) ?
C1 C2 C3 N3 . . . . -179.15(13) ?
C1 C2 C3 C4 . . . . -0.2(2) ?
N3 C3 C4 C12 . . . . -179.24(11) ?
C2 C3 C4 C12 . . . . 1.61(19) ?
N3 C3 C4 C5 . . . . 0.65(14) ?
C2 C3 C4 C5 . . . . -178.50(12) ?
C12 C4 C5 C21 . . . . 179.03(15) ?
C3 C4 C5 C21 . . . . -0.83(14) ?
C12 C4 C5 S1 . . . . -3.8(2) ?
C3 C4 C5 S1 . . . . 176.32(10) ?
C6 S1 C5 C21 . . . . 68.69(12) ?
C6 S1 C5 C4 . . . . -108.04(12) ?
C14 N1 C6 C7 . . . . 178.70(13) ?
C18 N1 C6 C7 . . . . -0.27(13) ?
C14 N1 C6 S1 . . . . -0.64(19) ?
C18 N1 C6 S1 . . . . -179.62(9) ?
C5 S1 C6 C7 . . . . -85.84(13) ?
C5 S1 C6 N1 . . . . 93.31(11) ?
C18 N2 C7 C6 . . . . 0.22(14) ?
C18 N2 C7 C8 . . . . 177.63(11) ?
N1 C6 C7 N2 . . . . 0.03(14) ?
S1 C6 C7 N2 . . . . 179.30(10) ?
N1 C6 C7 C8 . . . . -177.10(12) ?
S1 C6 C7 C8 . . . . 2.2(2) ?
N2 C7 C8 C9 . . . . 135.17(13) ?
C6 C7 C8 C9 . . . . -47.9(2) ?
N2 C7 C8 C20 . . . . -44.87(17) ?
C6 C7 C8 C20 . . . . 132.03(14) ?
C20 C8 C9 C10 . . . . 0.0(2) ?
C7 C8 C9 C10 . . . . 179.91(13) ?
C8 C9 C10 C11 . . . . -0.9(2) ?
C9 C10 C11 C19 . . . . 0.8(2) ?
C3 C4 C12 C13 . . . . -1.50(18) ?
C5 C4 C12 C13 . . . . 178.65(14) ?
C3 C4 C12 Cl1 . . . . 177.91(9) ?
C5 C4 C12 Cl1 . . . . -1.9(2) ?
C4 C12 C13 C1 . . . . 0.0(2) ?
Cl1 C12 C13 C1 . . . . -179.41(10) ?
C2 C1 C13 C12 . . . . 1.5(2) ?
C18 N1 C14 C15 . . . . 0.1(2) ?
C6 N1 C14 C15 . . . . -178.77(13) ?
N1 C14 C15 C16 . . . . -0.8(2) ?
C14 C15 C16 C17 . . . . 0.5(2) ?
C15 C16 C17 C18 . . . . 0.5(2) ?
C7 N2 C18 N1 . . . . -0.40(14) ?
C7 N2 C18 C17 . . . . -179.92(14) ?
C14 N1 C18 N2 . . . . -178.65(11) ?
C6 N1 C18 N2 . . . . 0.42(14) ?
C14 N1 C18 C17 . . . . 0.93(19) ?
C6 N1 C18 C17 . . . . -179.99(12) ?
C16 C17 C18 N2 . . . . 178.28(14) ?
C16 C17 C18 N1 . . . . -1.2(2) ?
C10 C11 C19 C20 . . . . 0.2(2) ?
C11 C19 C20 C8 . . . . -1.2(2) ?
C9 C8 C20 C19 . . . . 1.1(2) ?
C7 C8 C20 C19 . . . . -178.89(14) ?
C3 N3 C21 C5 . . . . -0.31(16) ?
C4 C5 C21 N3 . . . . 0.72(15) ?
S1 C5 C21 N3 . . . . -176.65(9) ?

####################################################################### 
# 
# 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_20190515GT
_database_code_depnum_ccdc_archive 'CCDC 1959799'
loop_
_audit_author_name
_audit_author_address
'Tao Guo'
;Henan University of Technology
China
;
_audit_update_record             
;
2019-10-17 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         331.42
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.0283(5)
_cell_length_b                   10.5630(7)
_cell_length_c                   19.1653(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1625.27(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9850
_cell_measurement_theta_min      2.3053
_cell_measurement_theta_max      72.4586
_cell_measurement_temperature    194.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696

_exptl_absorpt_coefficient_mu    1.796
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_T_max  0.81

_exptl_special_details           
;
;

_diffrn_ambient_temperature      194.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'cu k\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'd8 venture '
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            9361
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_theta_min         4.61
_diffrn_reflns_theta_max         72.45
_diffrn_reflns_theta_full        72.45
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

_refine_special_details          
;
;

_reflns_number_total             2875
_reflns_number_gt                2867
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.1178
_refine_ls_wR_factor_gt          0.2958
_refine_ls_wR_factor_ref         0.2959
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.094
_refine_ls_number_reflns         2875
_refine_ls_number_parameters     222
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1057P)²+11.9655P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.139
_refine_diff_density_min         -0.543
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1025 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.414(19)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.4778(4) 0.0253(2) 0.29484(13) 0.0385(7) Uani d . . . 1 . .
N N1 0.7484(14) 0.3635(9) 0.5171(5) 0.041(2) Uani d . . . 1 . .
H H6 0.817(12) 0.325(10) 0.544(5) 0.01(2) Uiso d . . . 1 . .
N N2 0.6163(14) 0.1060(10) 0.1671(5) 0.042(2) Uani d . . . 1 . .
C C1 0.730(2) 0.4985(11) 0.5183(7) 0.049(3) Uani d . . . 1 . .
H H1 0.78903 0.535559 0.47853 0.074 Uiso calc U . R 1 . .
H H3 0.776015 0.532094 0.561831 0.074 Uiso calc U . R 1 . .
H H17 0.611214 0.52024 0.515312 0.074 Uiso calc U . R 1 . .
N N3 0.4145(16) 0.2271(10) 0.1197(5) 0.053(3) Uani d . . . 1 . .
C C2 0.6859(12) 0.2900(10) 0.4633(5) 0.030(2) Uani d . . . 1 . .
C C3 0.7131(14) 0.1588(10) 0.4634(5) 0.034(2) Uani d . . . 1 . .
H H16 0.775174 0.1224 0.500533 0.04 Uiso calc U . R 1 . .
C C4 0.6532(14) 0.0807(10) 0.4115(5) 0.031(2) Uani d . . . 1 . .
H H4 0.673965 -0.007769 0.412761 0.037 Uiso calc U . R 1 . .
C C5 0.5613(11) 0.1341(9) 0.3571(5) 0.0249(19) Uani d . . . 1 . .
C C6 0.4849(17) 0.1130(10) 0.2167(6) 0.046(3) Uani d . . . 1 . .
C C7 0.3712(14) 0.1864(10) 0.1822(5) 0.043(3) Uani d . . D 1 . .
C C8 0.2016(12) 0.2319(12) 0.2077(9) 0.055(4) Uani d . . D 1 . .
C C9 0.1397(19) 0.2004(11) 0.2762(8) 0.063(5) Uani d . . . 1 . .
H H7 0.202343 0.147708 0.306589 0.075 Uiso calc U . R 1 . .
C C10 -0.0186(14) 0.2504(11) 0.2974(7) 0.044(3) Uani d . . . 1 . .
H H10 -0.065107 0.230357 0.341598 0.053 Uiso calc U . R 1 . .
C C11 -0.1000(17) 0.3280(12) 0.2516(8) 0.054(4) Uani d . . . 1 . .
H H2 -0.203845 0.363584 0.265061 0.064 Uiso calc U . R 1 . .
C C12 0.7568(17) 0.0455(12) 0.1731(6) 0.045(3) Uani d . . . 1 . .
H H13 0.779752 -0.001503 0.214218 0.054 Uiso calc U . R 1 . .
C C13 0.8677(14) 0.0490(11) 0.1221(7) 0.041(3) Uani d . . . 1 . .
H H5 0.970472 0.005518 0.127376 0.05 Uiso calc U . R 1 . .
C C14 0.8351(16) 0.1183(11) 0.0582(6) 0.043(3) Uani d . . . 1 . .
H H12 0.913038 0.119599 0.020949 0.052 Uiso calc U . R 1 . .
C C15 0.684(3) 0.1828(12) 0.0541(7) 0.070(5) Uani d . . . 1 . .
H H11 0.655962 0.231222 0.014021 0.083 Uiso calc U . R 1 . .
C C16 0.5718(14) 0.1737(12) 0.1123(8) 0.045(3) Uani d . . . 1 . .
C C18 -0.040(2) 0.3555(13) 0.1891(8) 0.060(4) Uani d . . . 1 . .
H H9 -0.101106 0.40964 0.159113 0.072 Uiso calc U . R 1 . .
C C19 0.1000(19) 0.3107(13) 0.1682(7) 0.051(3) Uani d . . . 1 . .
H H8 0.136443 0.332774 0.122663 0.062 Uiso calc U . R 1 . .
C C20 0.5289(12) 0.2625(9) 0.3569(5) 0.0262(19) Uani d . . . 1 . .
H H15 0.463029 0.297897 0.320614 0.031 Uiso calc U . R 1 . .
C C21 0.5915(13) 0.3403(9) 0.4090(5) 0.030(2) Uani d . . . 1 . .
H H14 0.569698 0.428643 0.407681 0.036 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C6 . 1.762(11) ?
S1 C5 . 1.788(10) ?
N1 C2 . 1.385(13) ?
N1 C1 . 1.434(15) ?
N1 H6 . 0.85(10) ?
N2 C12 . 1.301(17) ?
N2 C16 . 1.321(18) ?
N2 C6 . 1.421(17) ?
C1 H1 . 0.98 ?
C1 H3 . 0.98 ?
C1 H17 . 0.98 ?
N3 C7 . 1.320(15) ?
N3 C16 . 1.390(17) ?
C2 C21 . 1.392(13) ?
C2 C3 . 1.404(15) ?
C3 C4 . 1.378(15) ?
C3 H16 . 0.95 ?
C4 C5 . 1.396(13) ?
C4 H4 . 0.95 ?
C5 C20 . 1.380(13) ?
C6 C7 . 1.367(15) ?
C7 C8 . 1.525(11) ?
C8 C19 . 1.39(2) ?
C8 C9 . 1.44(2) ?
C9 C10 . 1.435(19) ?
C9 H7 . 0.95 ?
C10 C11 . 1.368(17) ?
C10 H10 . 0.95 ?
C11 C18 . 1.32(2) ?
C11 H2 . 0.95 ?
C12 C13 . 1.323(17) ?
C12 H13 . 0.95 ?
C13 C14 . 1.449(18) ?
C13 H5 . 0.95 ?
C14 C15 . 1.39(2) ?
C14 H12 . 0.95 ?
C15 C16 . 1.44(2) ?
C15 H11 . 0.95 ?
C18 C19 . 1.28(2) ?
C18 H9 . 0.95 ?
C19 H8 . 0.95 ?
C20 C21 . 1.389(12) ?
C20 H15 . 0.95 ?
C21 H14 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 S1 C5 . . 102.6(5) ?
C2 N1 C1 . . 122.1(10) ?
C2 N1 H6 . . 115.(7) ?
C1 N1 H6 . . 122.(7) ?
C12 N2 C16 . . 124.8(12) ?
C12 N2 C6 . . 127.6(11) ?
C16 N2 C6 . . 107.6(11) ?
N1 C1 H1 . . 109.5 ?
N1 C1 H3 . . 109.5 ?
H1 C1 H3 . . 109.5 ?
N1 C1 H17 . . 109.5 ?
H1 C1 H17 . . 109.5 ?
H3 C1 H17 . . 109.5 ?
C7 N3 C16 . . 101.6(11) ?
N1 C2 C21 . . 122.7(10) ?
N1 C2 C3 . . 119.8(9) ?
C21 C2 C3 . . 117.5(9) ?
C4 C3 C2 . . 122.4(9) ?
C4 C3 H16 . . 118.8 ?
C2 C3 H16 . . 118.8 ?
C3 C4 C5 . . 118.8(10) ?
C3 C4 H4 . . 120.6 ?
C5 C4 H4 . . 120.6 ?
C20 C5 C4 . . 120.0(9) ?
C20 C5 S1 . . 123.9(7) ?
C4 C5 S1 . . 115.9(8) ?
C7 C6 N2 . . 101.7(10) ?
C7 C6 S1 . . 133.4(11) ?
N2 C6 S1 . . 124.4(9) ?
N3 C7 C6 . . 116.6(12) ?
N3 C7 C8 . . 115.0(12) ?
C6 C7 C8 . . 128.4(12) ?
C19 C8 C9 . . 115.6(10) ?
C19 C8 C7 . . 122.6(14) ?
C9 C8 C7 . . 121.7(14) ?
C10 C9 C8 . . 118.5(11) ?
C10 C9 H7 . . 120.7 ?
C8 C9 H7 . . 120.7 ?
C11 C10 C9 . . 117.5(12) ?
C11 C10 H10 . . 121.2 ?
C9 C10 H10 . . 121.2 ?
C18 C11 C10 . . 122.4(14) ?
C18 C11 H2 . . 118.8 ?
C10 C11 H2 . . 118.8 ?
N2 C12 C13 . . 120.3(12) ?
N2 C12 H13 . . 119.8 ?
C13 C12 H13 . . 119.8 ?
C12 C13 C14 . . 121.1(11) ?
C12 C13 H5 . . 119.5 ?
C14 C13 H5 . . 119.5 ?
C15 C14 C13 . . 116.9(10) ?
C15 C14 H12 . . 121.6 ?
C13 C14 H12 . . 121.6 ?
C14 C15 C16 . . 118.0(11) ?
C14 C15 H11 . . 121.0 ?
C16 C15 H11 . . 121.0 ?
N2 C16 N3 . . 112.6(12) ?
N2 C16 C15 . . 118.9(12) ?
N3 C16 C15 . . 128.5(14) ?
C19 C18 C11 . . 121.5(14) ?
C19 C18 H9 . . 119.2 ?
C11 C18 H9 . . 119.2 ?
C18 C19 C8 . . 124.4(13) ?
C18 C19 H8 . . 117.8 ?
C8 C19 H8 . . 117.8 ?
C5 C20 C21 . . 120.7(9) ?
C5 C20 H15 . . 119.7 ?
C21 C20 H15 . . 119.7 ?
C20 C21 C2 . . 120.6(9) ?
C20 C21 H14 . . 119.7 ?
C2 C21 H14 . . 119.7 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 C2 C21 . . . . -4.2(19) ?
C1 N1 C2 C3 . . . . 177.6(12) ?
N1 C2 C3 C4 . . . . 179.6(11) ?
C21 C2 C3 C4 . . . . 1.4(17) ?
C2 C3 C4 C5 . . . . -0.3(18) ?
C3 C4 C5 C20 . . . . -1.5(16) ?
C3 C4 C5 S1 . . . . -176.4(9) ?
C6 S1 C5 C20 . . . . 38.4(10) ?
C6 S1 C5 C4 . . . . -146.8(9) ?
C12 N2 C6 C7 . . . . -179.2(11) ?
C16 N2 C6 C7 . . . . 1.2(12) ?
C12 N2 C6 S1 . . . . -6.8(16) ?
C16 N2 C6 S1 . . . . 173.5(8) ?
C5 S1 C6 C7 . . . . -94.8(12) ?
C5 S1 C6 N2 . . . . 95.6(10) ?
C16 N3 C7 C6 . . . . 0.7(13) ?
C16 N3 C7 C8 . . . . 178.6(8) ?
N2 C6 C7 N3 . . . . -1.2(13) ?
S1 C6 C7 N3 . . . . -172.5(9) ?
N2 C6 C7 C8 . . . . -178.8(10) ?
S1 C6 C7 C8 . . . . 10.0(19) ?
N3 C7 C8 C19 . . . . -0.2(15) ?
C6 C7 C8 C19 . . . . 177.5(12) ?
N3 C7 C8 C9 . . . . -177.1(10) ?
C6 C7 C8 C9 . . . . 0.5(17) ?
C19 C8 C9 C10 . . . . 0.6(15) ?
C7 C8 C9 C10 . . . . 177.8(9) ?
C8 C9 C10 C11 . . . . -1.5(16) ?
C9 C10 C11 C18 . . . . 1.4(19) ?
C16 N2 C12 C13 . . . . 0.1(18) ?
C6 N2 C12 C13 . . . . -179.5(11) ?
N2 C12 C13 C14 . . . . -1.0(17) ?
C12 C13 C14 C15 . . . . 1.5(16) ?
C13 C14 C15 C16 . . . . -1.2(16) ?
C12 N2 C16 N3 . . . . 179.4(10) ?
C6 N2 C16 N3 . . . . -0.9(12) ?
C12 N2 C16 C15 . . . . 0.1(17) ?
C6 N2 C16 C15 . . . . 179.8(10) ?
C7 N3 C16 N2 . . . . 0.2(12) ?
C7 N3 C16 C15 . . . . 179.4(12) ?
C14 C15 C16 N2 . . . . 0.5(16) ?
C14 C15 C16 N3 . . . . -178.7(10) ?
C10 C11 C18 C19 . . . . 0.(2) ?
C11 C18 C19 C8 . . . . -1.(2) ?
C9 C8 C19 C18 . . . . 0.5(18) ?
C7 C8 C19 C18 . . . . -176.6(12) ?
C4 C5 C20 C21 . . . . 2.2(15) ?
S1 C5 C20 C21 . . . . 176.7(8) ?
C5 C20 C21 C2 . . . . -1.1(16) ?
N1 C2 C21 C20 . . . . -178.8(10) ?
C3 C2 C21 C20 . . . . -0.7(16) ?

