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

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

data_cu_8v00682_0m_4_a
_database_code_depnum_ccdc_archive 'CCDC 2208644'
loop_
_audit_author_name
_audit_author_address
'Georgina Rosair'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-09-21 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
_audit_creation_date             2021-12-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H11 B Cl2 N2 S'
_chemical_formula_sum            'C18 H11 B Cl2 N2 S'
_chemical_formula_weight         369.06
_chemical_melting_point          ?
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'
B B 0.0090 0.0039 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.5839(4)
_cell_length_b                   7.0849(3)
_cell_length_c                   18.9487(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.452(3)
_cell_angle_gamma                90
_cell_volume                     1554.64(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3727
_cell_measurement_temperature    101.0
_cell_measurement_theta_max      69.92
_cell_measurement_theta_min      3.82
_shelx_estimated_absorpt_T_max   0.906
_shelx_estimated_absorpt_T_min   0.501
_exptl_absorpt_coefficient_mu    5.008
_exptl_absorpt_correction_T_max  0.753298
_exptl_absorpt_correction_T_min  0.579505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 37138 reflections, Rint = 0.0661
 (23176 with I > 3sig(I), Rint = 0.0593)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            37138
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.087
_diffrn_reflns_theta_min         3.817
_diffrn_ambient_temperature      101.0
_diffrn_detector                 'Bruker PhotonIII detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2581
_reflns_number_total             2992
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+0.5896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0868
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.514(3)
 0.486(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.63159(4) 0.09774(7) 0.69202(3) 0.01741(14) Uani 1 1 d . . . . .
Cl2 Cl 0.61921(4) 0.52613(7) 0.69360(3) 0.01801(14) Uani 1 1 d . . . . .
S1 S 0.84389(4) 0.36647(8) 0.59946(3) 0.01704(14) Uani 1 1 d . . . . .
N1 N 0.70590(14) 0.3220(2) 0.58265(9) 0.0140(4) Uani 1 1 d . . . . .
N2 N 0.88933(15) 0.3180(3) 0.52208(9) 0.0159(4) Uani 1 1 d . . . . .
C1 C 0.69180(17) 0.2730(3) 0.51436(11) 0.0138(4) Uani 1 1 d . . . . .
C2 C 0.79986(17) 0.2686(3) 0.47955(11) 0.0145(4) Uani 1 1 d . . . . .
C3 C 0.80341(18) 0.2217(3) 0.40594(11) 0.0146(4) Uani 1 1 d . . . . .
C4 C 0.69806(18) 0.1838(3) 0.37400(11) 0.0164(4) Uani 1 1 d . . . . .
H4 H 0.696293 0.150105 0.325464 0.020 Uiso 1 1 calc R U . . .
C5 C 0.59145(18) 0.1924(3) 0.40965(11) 0.0155(4) Uani 1 1 d . . . . .
H5 H 0.522240 0.166021 0.383539 0.019 Uiso 1 1 calc R U . . .
C6 C 0.58372(17) 0.2370(3) 0.47998(11) 0.0136(4) Uani 1 1 d . . . . .
C7 C 0.47744(18) 0.2568(3) 0.52063(11) 0.0147(4) Uani 1 1 d . . . . .
C8 C 0.48576(17) 0.2977(3) 0.59356(11) 0.0145(4) Uani 1 1 d . . . . .
C9 C 0.38283(18) 0.3189(3) 0.63069(11) 0.0173(4) Uani 1 1 d . . . . .
H9 H 0.386835 0.347690 0.679665 0.021 Uiso 1 1 calc R U . . .
C10 C 0.27579(18) 0.2987(3) 0.59723(12) 0.0184(4) Uani 1 1 d . . . . .
H10 H 0.207314 0.311971 0.623336 0.022 Uiso 1 1 calc R U . . .
C11 C 0.26872(19) 0.2589(3) 0.52509(12) 0.0188(4) Uani 1 1 d . . . . .
H11 H 0.195410 0.245772 0.501986 0.023 Uiso 1 1 calc R U . . .
C12 C 0.36860(18) 0.2384(3) 0.48726(11) 0.0162(4) Uani 1 1 d . . . . .
H12 H 0.363355 0.211701 0.438157 0.019 Uiso 1 1 calc R U . . .
C13 C 0.91279(18) 0.2192(3) 0.36756(11) 0.0155(4) Uani 1 1 d . . . . .
C14 C 0.91753(19) 0.2964(3) 0.29963(11) 0.0176(4) Uani 1 1 d . . . . .
H14 H 0.849938 0.349766 0.278364 0.021 Uiso 1 1 calc R U . . .
C15 C 1.01959(19) 0.2958(3) 0.26312(11) 0.0192(5) Uani 1 1 d . . . . .
H15 H 1.021775 0.350233 0.217366 0.023 Uiso 1 1 calc R U . . .
C16 C 1.11871(18) 0.2159(3) 0.29306(11) 0.0184(4) Uani 1 1 d . . . . .
H16 H 1.188670 0.215113 0.267958 0.022 Uiso 1 1 calc R U . . .
C17 C 1.11457(18) 0.1371(3) 0.36021(11) 0.0173(4) Uani 1 1 d . . . . .
H17 H 1.181961 0.081184 0.380758 0.021 Uiso 1 1 calc R U . . .
C18 C 1.01295(18) 0.1393(3) 0.39746(11) 0.0175(4) Uani 1 1 d . . . . .
H18 H 1.011445 0.086322 0.443482 0.021 Uiso 1 1 calc R U . . .
B1 B 0.6051(2) 0.3142(3) 0.63654(12) 0.0152(5) 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 B1 1.880(3) . ?
Cl2 B1 1.855(2) . ?
S1 N1 1.6523(17) . ?
S1 N2 1.6074(18) . ?
N1 C1 1.346(3) . ?
N1 B1 1.571(3) . ?
N2 C2 1.343(3) . ?
C1 C2 1.430(3) . ?
C1 C6 1.420(3) . ?
C2 C3 1.435(3) . ?
C3 C4 1.375(3) . ?
C3 C13 1.477(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.424(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(3) . ?
C6 C7 1.475(3) . ?
C7 C8 1.413(3) . ?
C7 C12 1.402(3) . ?
C8 C9 1.408(3) . ?
C8 B1 1.591(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.396(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.401(3) . ?
C13 C18 1.398(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(3) . ?
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
N2 S1 N1 96.95(9) . . ?
C1 N1 S1 109.13(14) . . ?
C1 N1 B1 122.81(17) . . ?
B1 N1 S1 127.77(14) . . ?
C2 N2 S1 109.72(14) . . ?
N1 C1 C2 111.28(18) . . ?
N1 C1 C6 124.87(18) . . ?
C6 C1 C2 123.81(19) . . ?
N2 C2 C1 112.88(18) . . ?
N2 C2 C3 127.07(19) . . ?
C1 C2 C3 120.01(19) . . ?
C2 C3 C13 121.82(18) . . ?
C4 C3 C2 115.22(19) . . ?
C4 C3 C13 122.95(19) . . ?
C3 C4 H4 118.2 . . ?
C3 C4 C5 123.62(19) . . ?
C5 C4 H4 118.2 . . ?
C4 C5 H5 118.4 . . ?
C6 C5 C4 123.25(19) . . ?
C6 C5 H5 118.4 . . ?
C1 C6 C7 118.76(18) . . ?
C5 C6 C1 114.06(18) . . ?
C5 C6 C7 127.14(19) . . ?
C8 C7 C6 119.54(19) . . ?
C12 C7 C6 120.57(19) . . ?
C12 C7 C8 119.89(19) . . ?
C7 C8 B1 123.54(18) . . ?
C9 C8 C7 118.24(19) . . ?
C9 C8 B1 118.18(18) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.3(2) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.90(19) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C3 120.13(19) . . ?
C18 C13 C3 121.25(19) . . ?
C18 C13 C14 118.62(19) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(2) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.3(2) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
Cl2 B1 Cl1 108.88(12) . . ?
N1 B1 Cl1 106.19(14) . . ?
N1 B1 Cl2 107.13(15) . . ?
N1 B1 C8 108.68(17) . . ?
C8 B1 Cl1 110.70(15) . . ?
C8 B1 Cl2 114.85(16) . . ?

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
S1 N1 C1 C2 2.1(2) . . . . ?
S1 N1 C1 C6 -175.67(17) . . . . ?
S1 N1 B1 Cl1 -69.5(2) . . . . ?
S1 N1 B1 Cl2 46.8(2) . . . . ?
S1 N1 B1 C8 171.41(14) . . . . ?
S1 N2 C2 C1 0.0(2) . . . . ?
S1 N2 C2 C3 177.60(18) . . . . ?
N1 S1 N2 C2 1.05(16) . . . . ?
N1 C1 C2 N2 -1.4(2) . . . . ?
N1 C1 C2 C3 -179.19(18) . . . . ?
N1 C1 C6 C5 178.93(19) . . . . ?
N1 C1 C6 C7 1.1(3) . . . . ?
N2 S1 N1 C1 -1.87(16) . . . . ?
N2 S1 N1 B1 171.98(17) . . . . ?
N2 C2 C3 C4 -177.3(2) . . . . ?
N2 C2 C3 C13 1.3(3) . . . . ?
C1 N1 B1 Cl1 103.63(19) . . . . ?
C1 N1 B1 Cl2 -140.13(17) . . . . ?
C1 N1 B1 C8 -15.5(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C2 C3 C13 178.73(18) . . . . ?
C1 C6 C7 C8 -4.4(3) . . . . ?
C1 C6 C7 C12 174.48(19) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
C2 C1 C6 C7 -176.42(18) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C2 C3 C13 C14 -137.4(2) . . . . ?
C2 C3 C13 C18 43.2(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C3 C13 C14 C15 179.7(2) . . . . ?
C3 C13 C18 C17 179.44(19) . . . . ?
C4 C3 C13 C14 41.2(3) . . . . ?
C4 C3 C13 C18 -138.3(2) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 C7 177.3(2) . . . . ?
C5 C6 C7 C8 178.0(2) . . . . ?
C5 C6 C7 C12 -3.1(3) . . . . ?
C6 C1 C2 N2 176.37(19) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C6 C7 C8 C9 178.95(19) . . . . ?
C6 C7 C8 B1 -3.2(3) . . . . ?
C6 C7 C12 C11 -179.33(19) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C7 C8 B1 Cl1 -104.1(2) . . . . ?
C7 C8 B1 Cl2 132.08(19) . . . . ?
C7 C8 B1 N1 12.1(3) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C9 C8 B1 Cl1 73.7(2) . . . . ?
C9 C8 B1 Cl2 -50.1(2) . . . . ?
C9 C8 B1 N1 -170.03(18) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C7 0.2(3) . . . . ?
C12 C7 C8 C9 0.0(3) . . . . ?
C12 C7 C8 B1 177.8(2) . . . . ?
C13 C3 C4 C5 -177.60(19) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C14 C13 C18 C17 0.0(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 -0.6(3) . . . . ?
C16 C17 C18 C13 0.7(3) . . . . ?
C18 C13 C14 C15 -0.8(3) . . . . ?
B1 N1 C1 C2 -172.12(18) . . . . ?
B1 N1 C1 C6 10.1(3) . . . . ?
B1 C8 C9 C10 -177.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.514(3)
2 0.486(3)

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: slow evaporation from chloroform solution'
####################################################################### 
# 
# 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_8v00698_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2208649'
loop_
_audit_author_name
_audit_author_address
'Scott Dalgarno'
;Heriot Watt University 
United Kingdom
;
_audit_update_record             
;
2022-09-21 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_cu_8v00698_0m_a     
;
PROBLEM: Hirshfeld Test Diff for    C21      --C22      .        7.1 s.u.
RESPONSE: No doubt from other analytical data  that this is a phenyl ring so C21 and C22 are definitely carbon atoms
;
# Added during the CSD deposition process: Wednesday 21 September 2022 03:44 PM
# end Validation Reply Form

_audit_creation_date             2022-01-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 N2 S'
_chemical_formula_sum            'C24 H16 N2 S'
_chemical_formula_weight         364.45
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.4393(6)
_cell_length_b                   10.3703(5)
_cell_length_c                   17.1418(12)
_cell_angle_alpha                90
_cell_angle_beta                 107.199(3)
_cell_angle_gamma                90
_cell_volume                     1772.77(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.19
_cell_measurement_theta_min      5.40
_shelx_estimated_absorpt_T_max   0.751
_shelx_estimated_absorpt_T_min   0.668
_exptl_absorpt_coefficient_mu    1.689
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0701 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.8632.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22077
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.151
_diffrn_reflns_theta_min         5.403
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3345
_reflns_number_total             3468
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Apex 4'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.004
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3468
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+1.3907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0883
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.63133(3) 0.34349(3) 0.58338(2) 0.01604(11) Uani 1 1 d . . . . .
N1 N 0.66333(11) 0.49301(11) 0.60728(7) 0.0158(2) Uani 1 1 d . . . . .
N2 N 0.47401(12) 0.33464(11) 0.57734(7) 0.0156(2) Uani 1 1 d . . . . .
C1 C 0.54732(13) 0.54491(13) 0.61193(8) 0.0135(3) Uani 1 1 d . . . . .
C2 C 0.52749(14) 0.67689(13) 0.62941(8) 0.0147(3) Uani 1 1 d . . . . .
C3 C 0.40118(14) 0.70922(13) 0.63206(8) 0.0165(3) Uani 1 1 d . . . . .
H3 H 0.3844 0.7959 0.6441 0.020 Uiso 1 1 calc R U . . .
C4 C 0.29466(14) 0.61854(14) 0.61762(8) 0.0163(3) Uani 1 1 d . . . . .
H4 H 0.2105 0.6468 0.6219 0.020 Uiso 1 1 calc R U . . .
C5 C 0.30764(13) 0.49190(13) 0.59771(8) 0.0148(3) Uani 1 1 d . . . . .
C6 C 0.43781(13) 0.45393(13) 0.59464(8) 0.0137(3) Uani 1 1 d . . . . .
C7 C 0.63609(14) 0.77403(13) 0.64158(8) 0.0159(3) Uani 1 1 d . . . . .
C8 C 0.76209(15) 0.75343(14) 0.69739(9) 0.0195(3) Uani 1 1 d . . . . .
H8 H 0.7802 0.6749 0.7272 0.023 Uiso 1 1 calc R U . . .
C9 C 0.86112(16) 0.84691(16) 0.70969(9) 0.0236(3) Uani 1 1 d . . . . .
H9 H 0.9462 0.8323 0.7483 0.028 Uiso 1 1 calc R U . . .
C10 C 0.83690(16) 0.96165(15) 0.66610(10) 0.0252(3) Uani 1 1 d . . . . .
H10 H 0.9045 1.0259 0.6753 0.030 Uiso 1 1 calc R U . . .
C11 C 0.71278(17) 0.98160(15) 0.60894(11) 0.0285(4) Uani 1 1 d . . . . .
H11 H 0.6963 1.0589 0.5779 0.034 Uiso 1 1 calc R U . . .
C12 C 0.61282(16) 0.88899(15) 0.59705(10) 0.0237(3) Uani 1 1 d . . . . .
H12 H 0.5279 0.9039 0.5583 0.028 Uiso 1 1 calc R U . . .
C13 C 0.19264(13) 0.40003(13) 0.57830(8) 0.0153(3) Uani 1 1 d . . . . .
C14 C 0.11392(14) 0.38101(13) 0.63153(9) 0.0160(3) Uani 1 1 d . . . . .
C15 C 0.00248(14) 0.29929(14) 0.60713(9) 0.0189(3) Uani 1 1 d . . . . .
H15 H -0.0511 0.2863 0.6426 0.023 Uiso 1 1 calc R U . . .
C16 C -0.03134(14) 0.23690(15) 0.53231(9) 0.0209(3) Uani 1 1 d . . . . .
H16 H -0.1072 0.1816 0.5168 0.025 Uiso 1 1 calc R U . . .
C17 C 0.04669(14) 0.25589(15) 0.48002(9) 0.0206(3) Uani 1 1 d . . . . .
H17 H 0.0242 0.2135 0.4286 0.025 Uiso 1 1 calc R U . . .
C18 C 0.15719(14) 0.33667(14) 0.50294(9) 0.0182(3) Uani 1 1 d . . . . .
H18 H 0.2098 0.3492 0.4668 0.022 Uiso 1 1 calc R U . . .
C19 C 0.14515(14) 0.44412(14) 0.71315(9) 0.0173(3) Uani 1 1 d . . . . .
C20 C 0.27197(15) 0.43296(14) 0.77032(9) 0.0198(3) Uani 1 1 d . . . . .
H20 H 0.3392 0.3834 0.7571 0.024 Uiso 1 1 calc R U . . .
C21 C 0.30119(15) 0.49244(14) 0.84549(9) 0.0213(3) Uani 1 1 d . . . . .
H21 H 0.3881 0.4847 0.8833 0.026 Uiso 1 1 calc R U . . .
C22 C 0.20147(16) 0.56479(14) 0.86595(9) 0.0227(3) Uani 1 1 d . . . . .
H22 H 0.2203 0.6063 0.9175 0.027 Uiso 1 1 calc R U . . .
C23 C 0.07356(15) 0.57462(14) 0.80884(9) 0.0204(3) Uani 1 1 d . . . . .
H23 H 0.0055 0.6232 0.8219 0.025 Uiso 1 1 calc R U . . .
C24 C 0.04635(15) 0.51437(14) 0.73422(9) 0.0205(3) Uani 1 1 d . . . . .
H24 H -0.0409 0.5207 0.6966 0.025 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 N1 1.6133(12) . ?
S1 N2 1.6174(12) . ?
N1 C1 1.3490(18) . ?
N2 C6 1.3517(18) . ?
C1 C2 1.4291(19) . ?
C1 C6 1.4438(19) . ?
C2 C3 1.3743(19) . ?
C2 C7 1.4845(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.421(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(2) . ?
C5 C6 1.4306(19) . ?
C5 C13 1.4912(19) . ?
C7 C8 1.395(2) . ?
C7 C12 1.398(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.411(2) . ?
C13 C18 1.398(2) . ?
C14 C15 1.400(2) . ?
C14 C19 1.491(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.400(2) . ?
C19 C24 1.395(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.409(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.407(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.376(2) . ?
C24 H24 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
N1 S1 N2 101.59(6) . . ?
C1 N1 S1 106.04(9) . . ?
C6 N2 S1 106.17(9) . . ?
N1 C1 C2 125.64(12) . . ?
N1 C1 C6 113.41(12) . . ?
C2 C1 C6 120.93(12) . . ?
C1 C2 C7 121.83(12) . . ?
C3 C2 C1 116.13(12) . . ?
C3 C2 C7 122.02(13) . . ?
C2 C3 H3 118.6 . . ?
C2 C3 C4 122.81(13) . . ?
C4 C3 H3 118.6 . . ?
C3 C4 H4 118.4 . . ?
C5 C4 C3 123.12(13) . . ?
C5 C4 H4 118.4 . . ?
C4 C5 C6 115.90(12) . . ?
C4 C5 C13 122.29(12) . . ?
C6 C5 C13 121.79(12) . . ?
N2 C6 C1 112.79(12) . . ?
N2 C6 C5 126.17(12) . . ?
C5 C6 C1 121.04(12) . . ?
C8 C7 C2 121.22(13) . . ?
C8 C7 C12 118.78(13) . . ?
C12 C7 C2 119.99(13) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.42(14) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.56(15) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.39(14) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.28(15) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.54(15) . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C5 121.98(12) . . ?
C18 C13 C5 118.82(12) . . ?
C18 C13 C14 119.09(13) . . ?
C13 C14 C19 122.55(12) . . ?
C15 C14 C13 118.89(13) . . ?
C15 C14 C19 118.56(12) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.41(13) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.50(13) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.98(13) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.13(13) . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C14 121.32(13) . . ?
C24 C19 C14 119.94(13) . . ?
C24 C19 C20 118.73(14) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.29(14) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.68(14) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 118.98(14) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.45(14) . . ?
C24 C23 H23 119.8 . . ?
C19 C24 H24 119.6 . . ?
C23 C24 C19 120.86(14) . . ?
C23 C24 H24 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
S1 N1 C1 C2 -178.22(11) . . . . ?
S1 N1 C1 C6 -0.12(14) . . . . ?
S1 N2 C6 C1 -0.01(14) . . . . ?
S1 N2 C6 C5 -179.12(11) . . . . ?
N1 S1 N2 C6 -0.05(10) . . . . ?
N1 C1 C2 C3 -179.35(13) . . . . ?
N1 C1 C2 C7 2.4(2) . . . . ?
N1 C1 C6 N2 0.09(17) . . . . ?
N1 C1 C6 C5 179.25(12) . . . . ?
N2 S1 N1 C1 0.10(10) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C1 C2 C7 C8 -52.54(19) . . . . ?
C1 C2 C7 C12 127.83(15) . . . . ?
C2 C1 C6 N2 178.30(12) . . . . ?
C2 C1 C6 C5 -2.54(19) . . . . ?
C2 C3 C4 C5 -1.8(2) . . . . ?
C2 C7 C8 C9 -178.10(13) . . . . ?
C2 C7 C12 C11 178.83(14) . . . . ?
C3 C2 C7 C8 129.28(15) . . . . ?
C3 C2 C7 C12 -50.3(2) . . . . ?
C3 C4 C5 C6 1.9(2) . . . . ?
C3 C4 C5 C13 -176.55(13) . . . . ?
C4 C5 C6 N2 179.24(13) . . . . ?
C4 C5 C6 C1 0.19(19) . . . . ?
C4 C5 C13 C14 -53.24(19) . . . . ?
C4 C5 C13 C18 122.94(15) . . . . ?
C5 C13 C14 C15 176.09(13) . . . . ?
C5 C13 C14 C19 -4.2(2) . . . . ?
C5 C13 C18 C17 -176.39(13) . . . . ?
C6 C1 C2 C3 2.67(19) . . . . ?
C6 C1 C2 C7 -175.61(12) . . . . ?
C6 C5 C13 C14 128.38(14) . . . . ?
C6 C5 C13 C18 -55.44(18) . . . . ?
C7 C2 C3 C4 177.65(13) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
C8 C7 C12 C11 -0.8(2) . . . . ?
C8 C9 C10 C11 -0.9(2) . . . . ?
C9 C10 C11 C12 1.6(2) . . . . ?
C10 C11 C12 C7 -0.8(2) . . . . ?
C12 C7 C8 C9 1.5(2) . . . . ?
C13 C5 C6 N2 -2.3(2) . . . . ?
C13 C5 C6 C1 178.67(12) . . . . ?
C13 C14 C15 C16 0.2(2) . . . . ?
C13 C14 C19 C20 -53.7(2) . . . . ?
C13 C14 C19 C24 127.31(15) . . . . ?
C14 C13 C18 C17 -0.1(2) . . . . ?
C14 C15 C16 C17 -0.2(2) . . . . ?
C14 C19 C20 C21 179.33(13) . . . . ?
C14 C19 C24 C23 -179.21(13) . . . . ?
C15 C14 C19 C20 126.02(15) . . . . ?
C15 C14 C19 C24 -53.01(19) . . . . ?
C15 C16 C17 C18 0.0(2) . . . . ?
C16 C17 C18 C13 0.1(2) . . . . ?
C18 C13 C14 C15 -0.1(2) . . . . ?
C18 C13 C14 C19 179.59(13) . . . . ?
C19 C14 C15 C16 -179.47(13) . . . . ?
C19 C20 C21 C22 0.8(2) . . . . ?
C20 C19 C24 C23 1.7(2) . . . . ?
C20 C21 C22 C23 0.0(2) . . . . ?
C21 C22 C23 C24 0.1(2) . . . . ?
C22 C23 C24 C19 -1.0(2) . . . . ?
C24 C19 C20 C21 -1.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_8v00708_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2208650'
loop_
_audit_author_name
_audit_author_address
'Scott Dalgarno'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-09-21 deposited with the CCDC.	2023-02-01 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         ?
_chemical_formula_sum            'C20 H12 N2 S3'
_chemical_formula_weight         376.50

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      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                   6.87730(10)
_cell_length_b                   7.41610(10)
_cell_length_c                   16.8392(3)
_cell_angle_alpha                89.3640(7)
_cell_angle_beta                 85.3723(7)
_cell_angle_gamma                73.5196(7)
_cell_volume                     820.81(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1875
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.05
_cell_measurement_theta_min      5.28

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    4.157
_shelx_estimated_absorpt_T_min   0.316
_shelx_estimated_absorpt_T_max   0.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5537
_exptl_absorpt_correction_T_max  0.7538
_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                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18869
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.271
_diffrn_reflns_theta_max         74.485
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3306
_reflns_number_gt                3156
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0285P)²+0.5143P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3306
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0704
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.71784(5) 0.67617(4) 0.76205(2) 0.01760(10) Uani 1 1 d . . . . .
N1 N 0.70289(18) 0.66942(16) 0.66682(7) 0.0161(2) Uani 1 1 d . . . . .
C1 C 0.75320(19) 0.48596(18) 0.64597(8) 0.0120(3) Uani 1 1 d . . . . .
S2 S 1.16141(5) -0.12917(5) 0.75431(2) 0.01667(10) Uani 1 1 d . . . . .
N2 N 0.78430(18) 0.45513(16) 0.78256(7) 0.0150(2) Uani 1 1 d . . . . .
C2 C 0.79833(19) 0.36269(18) 0.71292(8) 0.0120(3) Uani 1 1 d . . . . .
S3 S 0.66317(6) 0.77496(5) 0.50067(2) 0.01663(13) Uani 0.871(2) 1 d . . P A 3
C3 C 0.85800(19) 0.16316(18) 0.70251(8) 0.0122(3) Uani 1 1 d . . . . .
C4 C 0.8649(2) 0.09811(18) 0.62596(8) 0.0136(3) Uani 1 1 d . . . . .
H4 H 0.899932 -0.033804 0.616817 0.016 Uiso 1 1 calc R U . . .
C5 C 0.8219(2) 0.21986(19) 0.55987(8) 0.0138(3) Uani 1 1 d . . . . .
H5 H 0.830077 0.165244 0.508501 0.017 Uiso 1 1 calc R U . . .
C6 C 0.76919(19) 0.41270(18) 0.56648(8) 0.0125(3) Uani 1 1 d . . . . .
C7 C 0.9269(2) 0.03724(18) 0.76912(8) 0.0132(3) Uani 1 1 d . . . . .
C8 C 0.8427(2) 0.03204(18) 0.84589(8) 0.0143(3) Uani 1 1 d . . . . .
C9 C 0.9736(2) -0.1082(2) 0.89204(8) 0.0183(3) Uani 1 1 d . . . . .
H9 H 0.941111 -0.130526 0.946489 0.022 Uiso 1 1 calc R U . . .
C10 C 1.1485(2) -0.2059(2) 0.85023(9) 0.0201(3) Uani 1 1 d . . . . .
H10 H 1.250852 -0.304446 0.871623 0.024 Uiso 1 1 calc R U . . .
C11 C 0.6356(2) 0.14007(19) 0.87658(8) 0.0153(3) Uani 1 1 d . . . . .
C12 C 0.4725(2) 0.16775(19) 0.82918(8) 0.0161(3) Uani 1 1 d . . . . .
H12 H 0.496520 0.122001 0.775761 0.019 Uiso 1 1 calc R U . . .
C13 C 0.2759(2) 0.2610(2) 0.85881(9) 0.0205(3) Uani 1 1 d . . . . .
H13 H 0.166324 0.278140 0.825899 0.025 Uiso 1 1 calc R U . . .
C14 C 0.2394(2) 0.3293(2) 0.93673(9) 0.0249(3) Uani 1 1 d . . . . .
H14 H 0.105068 0.393917 0.957076 0.030 Uiso 1 1 calc R U . . .
C15 C 0.3994(3) 0.3029(2) 0.98469(9) 0.0297(4) Uani 1 1 d . . . . .
H15 H 0.374687 0.349903 1.037919 0.036 Uiso 1 1 calc R U . . .
C16 C 0.5961(3) 0.2079(2) 0.95508(9) 0.0248(3) Uani 1 1 d . . . . .
H16 H 0.704769 0.188804 0.988560 0.030 Uiso 1 1 calc R U . . .
C17 C 0.7367(2) 0.53220(19) 0.49617(8) 0.0136(3) Uani 1 1 d . . . . .
S18 S 0.76238(18) 0.46054(19) 0.41427(7) 0.0317(4) Uani 0.129(2) 1 d . . P A 2
C18 C 0.76238(18) 0.46054(19) 0.41427(7) 0.0317(4) Uani 0.871(2) 1 d . . P A 1
H18 H 0.800910 0.332171 0.397998 0.038 Uiso 0.871(2) 1 calc R U P A 1
C19 C 0.7176(2) 0.6236(2) 0.36220(9) 0.0211(3) Uani 1 1 d . . . . .
H19 H 0.725096 0.611931 0.305837 0.025 Uiso 0.871(2) 1 calc R U P A 1
H19A H 0.725096 0.611931 0.305837 0.025 Uiso 0.129(2) 1 calc R U P A 2
C20 C 0.6646(2) 0.7931(2) 0.40024(9) 0.0214(3) Uani 1 1 d . . . . .
H20 H 0.631637 0.909772 0.373323 0.026 Uiso 0.871(2) 1 calc R U P A 3
H20A H 0.631637 0.909772 0.373323 0.026 Uiso 0.129(2) 1 calc R U P A 4
C1A C 0.66317(6) 0.77496(5) 0.50067(2) 0.01663(13) Uani 0.129(2) 1 d . . P A 4
H1A H 0.633361 0.864203 0.543192 0.020 Uiso 0.129(2) 1 calc R U P A 4


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

loop_
_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 N2 1.6134(12) . ?
S1 N1 1.6173(12) . ?
N1 C1 1.3484(17) . ?
C1 C6 1.4344(18) . ?
C1 C2 1.4407(18) . ?
S2 C10 1.7104(15) . ?
S2 C7 1.7319(14) . ?
N2 C2 1.3479(17) . ?
C2 C3 1.4277(18) . ?
S3 C20 1.6946(15) . ?
S3 C17 1.7271(14) . ?
C3 C4 1.3738(18) . ?
C3 C7 1.4717(18) . ?
C4 C5 1.4216(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3754(19) . ?
C5 H5 0.9500 . ?
C6 C17 1.4644(18) . ?
C7 C8 1.3779(19) . ?
C8 C9 1.4349(19) . ?
C8 C11 1.477(2) . ?
C9 C10 1.360(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.396(2) . ?
C11 C16 1.398(2) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.4626(19) . ?
C17 S18 1.4626(19) . ?
C17 C1A 1.7271(14) . ?
S18 C19 1.4613(18) . ?
C18 C19 1.4613(18) . ?
C18 H18 0.9500 . ?
C19 C20 1.357(2) . ?
C19 H19 0.9500 . ?
C19 H19A 0.9500 . ?
C20 C1A 1.6946(15) . ?
C20 H20 0.9500 . ?
C20 H20A 0.9500 . ?
C1A H1A 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
N2 S1 N1 101.28(6) . . ?
C1 N1 S1 106.32(9) . . ?
N1 C1 C6 125.87(12) . . ?
N1 C1 C2 112.88(11) . . ?
C6 C1 C2 121.22(12) . . ?
C10 S2 C7 92.29(7) . . ?
C2 N2 S1 106.21(9) . . ?
N2 C2 C3 125.58(12) . . ?
N2 C2 C1 113.30(11) . . ?
C3 C2 C1 121.09(12) . . ?
C20 S3 C17 92.53(7) . . ?
C4 C3 C2 116.07(12) . . ?
C4 C3 C7 122.55(12) . . ?
C2 C3 C7 121.12(11) . . ?
C3 C4 C5 122.77(12) . . ?
C3 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
C6 C5 C4 123.35(12) . . ?
C6 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C5 C6 C1 115.43(12) . . ?
C5 C6 C17 121.41(12) . . ?
C1 C6 C17 123.15(12) . . ?
C8 C7 C3 131.48(12) . . ?
C8 C7 S2 111.15(10) . . ?
C3 C7 S2 117.26(10) . . ?
C7 C8 C9 111.58(12) . . ?
C7 C8 C11 125.60(12) . . ?
C9 C8 C11 122.53(12) . . ?
C10 C9 C8 113.42(13) . . ?
C10 C9 H9 123.3 . . ?
C8 C9 H9 123.3 . . ?
C9 C10 S2 111.55(11) . . ?
C9 C10 H10 124.2 . . ?
S2 C10 H10 124.2 . . ?
C12 C11 C16 118.36(13) . . ?
C12 C11 C8 120.65(12) . . ?
C16 C11 C8 120.90(13) . . ?
C13 C12 C11 121.05(13) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 119.88(14) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 119.88(14) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.14(14) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.69(15) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C18 C17 C6 124.14(12) . . ?
S18 C17 C6 124.14(12) . . ?
C6 C17 C1A 123.65(10) . . ?
C6 C17 S3 123.65(10) . . ?
C19 S18 C17 107.07(12) . . ?
C19 C18 C17 107.07(12) . . ?
C19 C18 H18 126.5 . . ?
C17 C18 H18 126.5 . . ?
C20 C19 S18 115.12(13) . . ?
C20 C19 C18 115.12(13) . . ?
C20 C19 H19 122.4 . . ?
C18 C19 H19 122.4 . . ?
C20 C19 H19A 122.4 . . ?
S18 C19 H19A 122.4 . . ?
C19 C20 C1A 113.06(11) . . ?
C19 C20 S3 113.06(11) . . ?
C19 C20 H20 123.5 . . ?
S3 C20 H20 123.5 . . ?
C19 C20 H20A 123.5 . . ?
C1A C20 H20A 123.5 . . ?
C20 C1A C17 92.53(7) . . ?
C20 C1A H1A 133.7 . . ?
C17 C1A H1A 133.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 S1 N1 C1 -0.55(10) . . . . ?
S1 N1 C1 C6 -177.13(11) . . . . ?
S1 N1 C1 C2 0.90(13) . . . . ?
N1 S1 N2 C2 0.02(10) . . . . ?
S1 N2 C2 C3 178.40(11) . . . . ?
S1 N2 C2 C1 0.50(13) . . . . ?
N1 C1 C2 N2 -0.96(16) . . . . ?
C6 C1 C2 N2 177.17(11) . . . . ?
N1 C1 C2 C3 -178.97(11) . . . . ?
C6 C1 C2 C3 -0.83(19) . . . . ?
N2 C2 C3 C4 -179.10(12) . . . . ?
C1 C2 C3 C4 -1.35(18) . . . . ?
N2 C2 C3 C7 -4.9(2) . . . . ?
C1 C2 C3 C7 172.85(12) . . . . ?
C2 C3 C4 C5 1.90(19) . . . . ?
C7 C3 C4 C5 -172.22(12) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C1 -1.97(19) . . . . ?
C4 C5 C6 C17 176.75(12) . . . . ?
N1 C1 C6 C5 -179.69(13) . . . . ?
C2 C1 C6 C5 2.44(18) . . . . ?
N1 C1 C6 C17 1.6(2) . . . . ?
C2 C1 C6 C17 -176.26(12) . . . . ?
C4 C3 C7 C8 -136.23(15) . . . . ?
C2 C3 C7 C8 49.9(2) . . . . ?
C4 C3 C7 S2 48.01(16) . . . . ?
C2 C3 C7 S2 -125.82(11) . . . . ?
C10 S2 C7 C8 -0.12(11) . . . . ?
C10 S2 C7 C3 176.48(11) . . . . ?
C3 C7 C8 C9 -175.41(13) . . . . ?
S2 C7 C8 C9 0.55(14) . . . . ?
C3 C7 C8 C11 10.8(2) . . . . ?
S2 C7 C8 C11 -173.23(10) . . . . ?
C7 C8 C9 C10 -0.86(17) . . . . ?
C11 C8 C9 C10 173.15(12) . . . . ?
C8 C9 C10 S2 0.76(16) . . . . ?
C7 S2 C10 C9 -0.37(12) . . . . ?
C7 C8 C11 C12 38.1(2) . . . . ?
C9 C8 C11 C12 -135.06(14) . . . . ?
C7 C8 C11 C16 -145.56(14) . . . . ?
C9 C8 C11 C16 41.3(2) . . . . ?
C16 C11 C12 C13 0.3(2) . . . . ?
C8 C11 C12 C13 176.78(12) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C14 C15 C16 C11 0.9(2) . . . . ?
C12 C11 C16 C15 -0.9(2) . . . . ?
C8 C11 C16 C15 -177.37(14) . . . . ?
C5 C6 C17 C18 -1.9(2) . . . . ?
C1 C6 C17 C18 176.69(12) . . . . ?
C5 C6 C17 S18 -1.9(2) . . . . ?
C1 C6 C17 S18 176.69(12) . . . . ?
C5 C6 C17 C1A 178.07(10) . . . . ?
C1 C6 C17 C1A -3.31(18) . . . . ?
C5 C6 C17 S3 178.07(10) . . . . ?
C1 C6 C17 S3 -3.31(18) . . . . ?
C20 S3 C17 C6 179.58(12) . . . . ?
C6 C17 S18 C19 -179.48(12) . . . . ?
C6 C17 C18 C19 -179.48(12) . . . . ?
C17 S18 C19 C20 -0.39(17) . . . . ?
C17 C18 C19 C20 -0.39(17) . . . . ?
C17 S3 C20 C19 0.20(12) . . . . ?
C19 C20 C1A C17 0.20(12) . . . . ?
C6 C17 C1A C20 179.58(12) . . . . ?

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_8v00727_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2208651'
loop_
_audit_author_name
_audit_author_address
'Scott Dalgarno'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-09-21 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
_audit_creation_date             2022-02-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H16 N2 S3'
_chemical_formula_sum            'C26 H16 N2 S3'
_chemical_formula_weight         452.59
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.9159(3)
_cell_length_b                   9.8182(3)
_cell_length_c                   10.8445(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.7930(10)
_cell_angle_gamma                90
_cell_volume                     1033.50(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7689
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      79.22
_cell_measurement_theta_min      4.56
_shelx_estimated_absorpt_T_max   0.549
_shelx_estimated_absorpt_T_min   0.549
_exptl_absorpt_coefficient_mu    3.407
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0909 before and 0.0530 after correction.
The Ratio of minimum to maximum transmission is 0.8742.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27584
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_min         5.511
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                3613
_reflns_number_total             3619
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1658 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0224
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0319P)²+0.2824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0585
_refine_ls_wR_factor_ref         0.0586
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.47731(5) 0.93151(5) 0.71500(5) 0.01622(14) Uani 1 1 d . . . . .
S2 S 0.73855(5) 0.68175(6) 0.49777(5) 0.01638(14) Uani 1 1 d . . . . .
S3 S 0.07144(5) 0.73748(5) 0.76910(5) 0.01709(14) Uani 1 1 d . . . . .
N1 N 0.5712(2) 0.81843(19) 0.66424(18) 0.0156(4) Uani 1 1 d . . . . .
N2 N 0.35467(19) 0.83728(19) 0.74606(17) 0.0145(4) Uani 1 1 d . . . . .
C1 C 0.5078(2) 0.6979(2) 0.66799(18) 0.0127(4) Uani 1 1 d . . . . .
C2 C 0.5542(2) 0.5689(2) 0.6305(2) 0.0127(4) Uani 1 1 d . . . . .
C3 C 0.4678(2) 0.4606(2) 0.63675(19) 0.0133(4) Uani 1 1 d . . . . .
H3 H 0.4910 0.3744 0.6072 0.016 Uiso 1 1 calc R U . . .
C4 C 0.3460(2) 0.4715(2) 0.68509(19) 0.0143(4) Uani 1 1 d . . . . .
H4 H 0.2920 0.3919 0.6872 0.017 Uiso 1 1 calc R U . . .
C5 C 0.3016(2) 0.5915(2) 0.72924(19) 0.0131(4) Uani 1 1 d . . . . .
C6 C 0.3825(2) 0.7088(2) 0.71576(18) 0.0135(4) Uani 1 1 d . . . . .
C7 C 0.8713(2) 0.5849(3) 0.4671(2) 0.0185(5) Uani 1 1 d . . . . .
H7 H 0.9344 0.6144 0.4174 0.022 Uiso 1 1 calc R U . . .
C8 C 0.8752(2) 0.4606(2) 0.5225(2) 0.0162(5) Uani 1 1 d . . . . .
H8 H 0.9426 0.3935 0.5164 0.019 Uiso 1 1 calc R U . . .
C9 C 0.7681(2) 0.4405(2) 0.59085(19) 0.0137(4) Uani 1 1 d . . . . .
C10 C 0.6827(2) 0.5528(2) 0.5846(2) 0.0138(4) Uani 1 1 d . . . . .
C11 C 0.7628(2) 0.3126(2) 0.6628(2) 0.0134(4) Uani 1 1 d . . . . .
C12 C 0.7897(2) 0.1881(3) 0.61057(19) 0.0156(4) Uani 1 1 d . . . . .
H12 H 0.8013 0.1853 0.5258 0.019 Uiso 1 1 calc R U . . .
C13 C 0.7997(2) 0.0680(2) 0.6798(2) 0.0178(5) Uani 1 1 d . . . . .
H13 H 0.8177 -0.0157 0.6423 0.021 Uiso 1 1 calc R U . . .
C14 C 0.7835(2) 0.0712(2) 0.8041(2) 0.0189(5) Uani 1 1 d . . . . .
H14 H 0.7925 -0.0100 0.8527 0.023 Uiso 1 1 calc R U . . .
C15 C 0.7538(2) 0.1944(3) 0.8569(2) 0.0172(4) Uani 1 1 d . . . . .
H15 H 0.7414 0.1966 0.9415 0.021 Uiso 1 1 calc R U . . .
C16 C 0.7424(2) 0.3140(2) 0.7868(2) 0.0149(4) Uani 1 1 d . . . . .
H16 H 0.7206 0.3970 0.8233 0.018 Uiso 1 1 calc R U . . .
C17 C -0.0405(2) 0.6593(2) 0.8477(2) 0.0190(5) Uani 1 1 d . . . . .
H17 H -0.1235 0.6990 0.8613 0.023 Uiso 1 1 calc R U . . .
C18 C 0.0046(2) 0.5331(2) 0.8882(2) 0.0165(5) Uani 1 1 d . . . . .
H18 H -0.0434 0.4755 0.9350 0.020 Uiso 1 1 calc R U . . .
C19 C 0.1305(2) 0.4954(2) 0.85407(19) 0.0144(4) Uani 1 1 d . . . . .
C20 C 0.1802(2) 0.5972(2) 0.7873(2) 0.0137(4) Uani 1 1 d . . . . .
C21 C 0.1980(2) 0.3621(2) 0.88917(19) 0.0139(4) Uani 1 1 d . . . . .
C22 C 0.1278(2) 0.2406(3) 0.8529(2) 0.0165(4) Uani 1 1 d . . . . .
H22 H 0.0349 0.2436 0.8080 0.020 Uiso 1 1 calc R U . . .
C23 C 0.1917(3) 0.1158(2) 0.8813(2) 0.0199(5) Uani 1 1 d . . . . .
H23 H 0.1429 0.0341 0.8549 0.024 Uiso 1 1 calc R U . . .
C24 C 0.3269(3) 0.1097(3) 0.9484(2) 0.0214(5) Uani 1 1 d . . . . .
H24 H 0.3706 0.0241 0.9680 0.026 Uiso 1 1 calc R U . . .
C25 C 0.3978(2) 0.2295(3) 0.9867(2) 0.0212(5) Uani 1 1 d . . . . .
H25 H 0.4899 0.2257 1.0332 0.025 Uiso 1 1 calc R U . . .
C26 C 0.3343(2) 0.3547(2) 0.9570(2) 0.0171(5) Uani 1 1 d . . . . .
H26 H 0.3836 0.4362 0.9830 0.021 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 N1 1.616(2) . ?
S1 N2 1.617(2) . ?
S2 C7 1.711(2) . ?
S2 C10 1.735(2) . ?
S3 C17 1.713(2) . ?
S3 C20 1.735(2) . ?
N1 C1 1.345(3) . ?
N2 C6 1.346(3) . ?
C1 C2 1.434(3) . ?
C1 C6 1.445(3) . ?
C2 C3 1.376(3) . ?
C2 C10 1.468(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.416(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(3) . ?
C5 C6 1.428(3) . ?
C5 C20 1.469(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.357(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.428(3) . ?
C9 C10 1.384(3) . ?
C9 C11 1.485(3) . ?
C11 C12 1.396(3) . ?
C11 C16 1.401(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.395(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.391(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.359(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.422(3) . ?
C19 C20 1.383(3) . ?
C19 C21 1.484(3) . ?
C21 C22 1.397(3) . ?
C21 C26 1.402(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.390(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.389(4) . ?
C26 H26 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
N1 S1 N2 100.84(10) . . ?
C7 S2 C10 92.50(12) . . ?
C17 S3 C20 92.20(11) . . ?
C1 N1 S1 106.78(15) . . ?
C6 N2 S1 106.56(15) . . ?
N1 C1 C2 126.11(19) . . ?
N1 C1 C6 112.78(19) . . ?
C2 C1 C6 121.10(19) . . ?
C1 C2 C10 122.85(19) . . ?
C3 C2 C1 115.4(2) . . ?
C3 C2 C10 121.7(2) . . ?
C2 C3 H3 118.4 . . ?
C2 C3 C4 123.2(2) . . ?
C4 C3 H3 118.4 . . ?
C3 C4 H4 118.3 . . ?
C5 C4 C3 123.4(2) . . ?
C5 C4 H4 118.3 . . ?
C4 C5 C6 115.4(2) . . ?
C4 C5 C20 122.0(2) . . ?
C6 C5 C20 122.6(2) . . ?
N2 C6 C1 113.03(19) . . ?
N2 C6 C5 125.7(2) . . ?
C5 C6 C1 121.25(19) . . ?
S2 C7 H7 124.2 . . ?
C8 C7 S2 111.55(17) . . ?
C8 C7 H7 124.2 . . ?
C7 C8 H8 123.3 . . ?
C7 C8 C9 113.4(2) . . ?
C9 C8 H8 123.3 . . ?
C8 C9 C11 120.0(2) . . ?
C10 C9 C8 112.2(2) . . ?
C10 C9 C11 127.74(19) . . ?
C2 C10 S2 120.03(17) . . ?
C9 C10 S2 110.34(16) . . ?
C9 C10 C2 129.4(2) . . ?
C12 C11 C9 119.82(19) . . ?
C12 C11 C16 118.4(2) . . ?
C16 C11 C9 121.6(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.48(19) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.7(2) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.51(19) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.3(2) . . ?
C15 C16 H16 119.8 . . ?
S3 C17 H17 124.3 . . ?
C18 C17 S3 111.44(17) . . ?
C18 C17 H17 124.3 . . ?
C17 C18 H18 123.2 . . ?
C17 C18 C19 113.7(2) . . ?
C19 C18 H18 123.2 . . ?
C18 C19 C21 122.5(2) . . ?
C20 C19 C18 112.0(2) . . ?
C20 C19 C21 125.6(2) . . ?
C5 C20 S3 121.78(17) . . ?
C19 C20 S3 110.70(17) . . ?
C19 C20 C5 127.4(2) . . ?
C22 C21 C19 120.57(19) . . ?
C22 C21 C26 118.3(2) . . ?
C26 C21 C19 121.1(2) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 120.9(2) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.7(2) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.2(2) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 119.7 . . ?
C25 C26 C21 120.7(2) . . ?
C25 C26 H26 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 C2 179.49(17) . . . . ?
S1 N1 C1 C6 -0.7(2) . . . . ?
S1 N2 C6 C1 0.2(2) . . . . ?
S1 N2 C6 C5 179.29(16) . . . . ?
S2 C7 C8 C9 0.7(3) . . . . ?
S3 C17 C18 C19 -1.2(2) . . . . ?
N1 S1 N2 C6 -0.58(16) . . . . ?
N1 C1 C2 C3 -176.7(2) . . . . ?
N1 C1 C2 C10 1.5(3) . . . . ?
N1 C1 C6 N2 0.3(2) . . . . ?
N1 C1 C6 C5 -178.80(18) . . . . ?
N2 S1 N1 C1 0.75(16) . . . . ?
C1 C2 C3 C4 -4.4(3) . . . . ?
C1 C2 C10 S2 -33.7(3) . . . . ?
C1 C2 C10 C9 152.2(2) . . . . ?
C2 C1 C6 N2 -179.86(18) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C2 C10 S2 144.40(19) . . . . ?
C3 C2 C10 C9 -29.8(3) . . . . ?
C3 C4 C5 C6 4.0(3) . . . . ?
C3 C4 C5 C20 -175.46(19) . . . . ?
C4 C5 C6 N2 176.3(2) . . . . ?
C4 C5 C6 C1 -4.7(3) . . . . ?
C4 C5 C20 S3 -145.68(18) . . . . ?
C4 C5 C20 C19 29.8(3) . . . . ?
C6 C1 C2 C3 3.5(3) . . . . ?
C6 C1 C2 C10 -178.34(19) . . . . ?
C6 C5 C20 S3 34.9(3) . . . . ?
C6 C5 C20 C19 -149.6(2) . . . . ?
C7 S2 C10 C2 -173.73(18) . . . . ?
C7 S2 C10 C9 1.48(17) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C7 C8 C9 C11 -176.6(2) . . . . ?
C8 C9 C10 S2 -1.3(2) . . . . ?
C8 C9 C10 C2 173.3(2) . . . . ?
C8 C9 C11 C12 -41.6(3) . . . . ?
C8 C9 C11 C16 133.1(2) . . . . ?
C9 C11 C12 C13 173.23(19) . . . . ?
C9 C11 C16 C15 -172.45(19) . . . . ?
C10 S2 C7 C8 -1.24(19) . . . . ?
C10 C2 C3 C4 177.42(19) . . . . ?
C10 C9 C11 C12 141.9(2) . . . . ?
C10 C9 C11 C16 -43.5(3) . . . . ?
C11 C9 C10 S2 175.46(18) . . . . ?
C11 C9 C10 C2 -9.9(4) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C11 C16 C15 2.3(3) . . . . ?
C12 C13 C14 C15 1.6(3) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C14 C15 C16 C11 -1.1(3) . . . . ?
C16 C11 C12 C13 -1.6(3) . . . . ?
C17 S3 C20 C5 175.23(18) . . . . ?
C17 S3 C20 C19 -0.95(17) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C17 C18 C19 C21 179.82(19) . . . . ?
C18 C19 C20 S3 0.4(2) . . . . ?
C18 C19 C20 C5 -175.5(2) . . . . ?
C18 C19 C21 C22 57.5(3) . . . . ?
C18 C19 C21 C26 -123.9(2) . . . . ?
C19 C21 C22 C23 177.7(2) . . . . ?
C19 C21 C26 C25 -178.3(2) . . . . ?
C20 S3 C17 C18 1.23(18) . . . . ?
C20 C5 C6 N2 -4.2(3) . . . . ?
C20 C5 C6 C1 174.74(19) . . . . ?
C20 C19 C21 C22 -123.3(2) . . . . ?
C20 C19 C21 C26 55.4(3) . . . . ?
C21 C19 C20 S3 -178.87(16) . . . . ?
C21 C19 C20 C5 5.2(4) . . . . ?
C21 C22 C23 C24 0.9(3) . . . . ?
C22 C21 C26 C25 0.4(3) . . . . ?
C22 C23 C24 C25 -0.1(4) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C24 C25 C26 C21 0.4(3) . . . . ?
C26 C21 C22 C23 -1.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
