# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_8v00373_0m
_database_code_depnum_ccdc_archive 'CCDC 2179269'
loop_
_audit_author_name
_audit_author_address
'Georgina Rosair'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_audit_creation_date             2022-06-14
_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         'C20 H16 N2 S'
_chemical_formula_sum            'C20 H16 N2 S'
_chemical_formula_weight         316.41
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7484(4)
_cell_length_b                   10.8200(12)
_cell_length_c                   12.3382(11)
_cell_angle_alpha                88.148(5)
_cell_angle_beta                 87.502(3)
_cell_angle_gamma                89.861(3)
_cell_volume                     766.28(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      74.556
_cell_measurement_theta_min      5.347
_shelx_estimated_absorpt_T_max   0.836
_shelx_estimated_absorpt_T_min   0.482
_exptl_absorpt_coefficient_mu    1.860
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0970 before and 0.0474 after correction.
The Ratio of minimum to maximum transmission is 0.7213.
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    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11410
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.861
_diffrn_reflns_theta_min         5.355
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_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
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3024
_reflns_number_total             3082
_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 V8.40A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 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         0.396
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3082
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.061
_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)+(0.0521P)²+0.3126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15), C18(H18), C19(H19),
 C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_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 0.74581(5) 0.38690(3) 0.50392(2) 0.02079(12) Uani 1 1 d . . . . .
N2 N 0.85129(18) 0.46349(10) 0.39832(8) 0.0167(2) Uani 1 1 d . . . . .
N5 N 0.56580(18) 0.29636(10) 0.44958(8) 0.0176(2) Uani 1 1 d . . . . .
C3 C 0.7464(2) 0.41841(11) 0.31243(9) 0.0128(2) Uani 1 1 d . . . . .
C4 C 0.5818(2) 0.32167(10) 0.34193(9) 0.0131(2) Uani 1 1 d . . . . .
C6 C 0.45143(19) 0.26311(10) 0.26193(10) 0.0125(2) Uani 1 1 d . . . . .
C7 C 0.4933(2) 0.30616(11) 0.15692(9) 0.0136(2) Uani 1 1 d . . . . .
H7 H 0.410951 0.269564 0.101090 0.016 Uiso 1 1 calc R U . . .
C8 C 0.6534(2) 0.40260(11) 0.12754(9) 0.0135(2) Uani 1 1 d . . . . .
H8 H 0.671806 0.427987 0.053242 0.016 Uiso 1 1 calc R U . . .
C9 C 0.78280(19) 0.46072(10) 0.20167(9) 0.0121(2) Uani 1 1 d . . . . .
C10 C 0.94198(19) 0.56438(11) 0.17065(9) 0.0124(2) Uani 1 1 d . . . . .
C11 C 0.8765(2) 0.65388(11) 0.09355(10) 0.0146(2) Uani 1 1 d . . . . .
H11 H 0.734180 0.644750 0.058295 0.017 Uiso 1 1 calc R U . . .
C12 C 1.0165(2) 0.75585(11) 0.06780(10) 0.0157(2) Uani 1 1 d . . . . .
H12 H 0.967873 0.815790 0.015524 0.019 Uiso 1 1 calc R U . . .
C13 C 1.2270(2) 0.77185(11) 0.11726(10) 0.0149(2) Uani 1 1 d . . . . .
C14 C 1.2949(2) 0.68080(11) 0.19217(10) 0.0151(2) Uani 1 1 d . . . . .
H14 H 1.439380 0.688923 0.225833 0.018 Uiso 1 1 calc R U . . .
C15 C 1.1557(2) 0.57859(11) 0.21846(9) 0.0136(2) Uani 1 1 d . . . . .
H15 H 1.206245 0.517724 0.269477 0.016 Uiso 1 1 calc R U . . .
C16 C 1.3731(2) 0.88509(12) 0.09168(11) 0.0196(3) Uani 1 1 d . . . . .
H16A H 1.330022 0.949479 0.142924 0.029 Uiso 1 1 calc R U . . .
H16B H 1.346359 0.915439 0.017557 0.029 Uiso 1 1 calc R U . . .
H16C H 1.538003 0.864117 0.097891 0.029 Uiso 1 1 calc R U . . .
C17 C 0.28536(19) 0.16136(10) 0.28940(9) 0.0125(2) Uani 1 1 d . . . . .
C18 C 0.0770(2) 0.15367(11) 0.23567(10) 0.0145(2) Uani 1 1 d . . . . .
H18 H 0.036940 0.217401 0.185058 0.017 Uiso 1 1 calc R U . . .
C19 C -0.0721(2) 0.05374(11) 0.25549(10) 0.0153(2) Uani 1 1 d . . . . .
H19 H -0.212327 0.050058 0.217705 0.018 Uiso 1 1 calc R U . . .
C20 C -0.0202(2) -0.04109(11) 0.32966(10) 0.0145(2) Uani 1 1 d . . . . .
C21 C 0.1857(2) -0.03175(11) 0.38476(10) 0.0152(2) Uani 1 1 d . . . . .
H21 H 0.223781 -0.094628 0.436550 0.018 Uiso 1 1 calc R U . . .
C22 C 0.3359(2) 0.06749(11) 0.36543(9) 0.0144(2) Uani 1 1 d . . . . .
H22 H 0.474640 0.071726 0.404272 0.017 Uiso 1 1 calc R U . . .
C23 C -0.1782(2) -0.15096(11) 0.34988(11) 0.0181(3) Uani 1 1 d . . . . .
H23A H -0.329201 -0.133479 0.318738 0.027 Uiso 1 1 calc R U . . .
H23B H -0.200451 -0.167440 0.428215 0.027 Uiso 1 1 calc R U . . .
H23C H -0.107832 -0.223476 0.315864 0.027 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 N2 1.6174(10) . ?
S1 N5 1.6087(10) . ?
N2 C3 1.3472(15) . ?
N5 C4 1.3467(15) . ?
C3 C4 1.4400(15) . ?
C3 C9 1.4339(16) . ?
C4 C6 1.4298(16) . ?
C6 C7 1.3740(16) . ?
C6 C17 1.4802(15) . ?
C7 H7 0.9500 . ?
C7 C8 1.4208(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.3724(16) . ?
C9 C10 1.4793(15) . ?
C10 C11 1.3979(16) . ?
C10 C15 1.3967(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.3876(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3924(17) . ?
C13 C14 1.3957(17) . ?
C13 C16 1.5043(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.3884(16) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.3977(16) . ?
C17 C22 1.3990(16) . ?
C18 H18 0.9500 . ?
C18 C19 1.3904(16) . ?
C19 H19 0.9500 . ?
C19 C20 1.3932(17) . ?
C20 C21 1.3958(17) . ?
C20 C23 1.5057(16) . ?
C21 H21 0.9500 . ?
C21 C22 1.3876(16) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 S1 N2 101.19(5) . . ?
C3 N2 S1 106.19(8) . . ?
C4 N5 S1 106.62(8) . . ?
N2 C3 C4 113.14(10) . . ?
N2 C3 C9 125.80(11) . . ?
C9 C3 C4 121.05(10) . . ?
N5 C4 C3 112.87(10) . . ?
N5 C4 C6 125.78(11) . . ?
C6 C4 C3 121.35(10) . . ?
C4 C6 C17 122.59(10) . . ?
C7 C6 C4 115.50(10) . . ?
C7 C6 C17 121.90(10) . . ?
C6 C7 H7 118.3 . . ?
C6 C7 C8 123.38(11) . . ?
C8 C7 H7 118.3 . . ?
C7 C8 H8 118.5 . . ?
C9 C8 C7 122.96(11) . . ?
C9 C8 H8 118.5 . . ?
C3 C9 C10 121.75(10) . . ?
C8 C9 C3 115.76(10) . . ?
C8 C9 C10 122.43(10) . . ?
C11 C10 C9 119.83(10) . . ?
C15 C10 C9 122.07(10) . . ?
C15 C10 C11 118.07(11) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 120.92(11) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.14(11) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C14 117.86(11) . . ?
C12 C13 C16 120.64(11) . . ?
C14 C13 C16 121.49(11) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.33(11) . . ?
C15 C14 H14 119.3 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.64(11) . . ?
C14 C15 H15 119.7 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C6 120.37(10) . . ?
C18 C17 C22 118.09(10) . . ?
C22 C17 C6 121.47(10) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.71(11) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.33(11) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C21 117.75(11) . . ?
C19 C20 C23 121.69(11) . . ?
C21 C20 C23 120.56(11) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 C20 121.36(11) . . ?
C22 C21 H21 119.3 . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.73(10) . . ?
C21 C22 H22 119.6 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N2 C3 C4 0.25(12) . . . . ?
S1 N2 C3 C9 178.62(10) . . . . ?
S1 N5 C4 C3 -0.57(12) . . . . ?
S1 N5 C4 C6 -179.72(10) . . . . ?
N2 S1 N5 C4 0.65(10) . . . . ?
N2 C3 C4 N5 0.22(15) . . . . ?
N2 C3 C4 C6 179.41(11) . . . . ?
N2 C3 C9 C8 -178.83(11) . . . . ?
N2 C3 C9 C10 -1.52(18) . . . . ?
N5 S1 N2 C3 -0.53(9) . . . . ?
N5 C4 C6 C7 178.59(11) . . . . ?
N5 C4 C6 C17 -2.47(18) . . . . ?
C3 C4 C6 C7 -0.49(16) . . . . ?
C3 C4 C6 C17 178.44(10) . . . . ?
C3 C9 C10 C11 -137.88(12) . . . . ?
C3 C9 C10 C15 40.17(16) . . . . ?
C4 C3 C9 C8 -0.57(16) . . . . ?
C4 C3 C9 C10 176.74(10) . . . . ?
C4 C6 C7 C8 -0.29(16) . . . . ?
C4 C6 C17 C18 142.43(12) . . . . ?
C4 C6 C17 C22 -40.61(16) . . . . ?
C6 C7 C8 C9 0.67(18) . . . . ?
C6 C17 C18 C19 175.44(11) . . . . ?
C6 C17 C22 C21 -175.51(11) . . . . ?
C7 C6 C17 C18 -38.70(16) . . . . ?
C7 C6 C17 C22 138.26(12) . . . . ?
C7 C8 C9 C3 -0.21(16) . . . . ?
C7 C8 C9 C10 -177.50(10) . . . . ?
C8 C9 C10 C11 39.25(16) . . . . ?
C8 C9 C10 C15 -142.71(12) . . . . ?
C9 C3 C4 N5 -178.25(10) . . . . ?
C9 C3 C4 C6 0.95(17) . . . . ?
C9 C10 C11 C12 176.15(10) . . . . ?
C9 C10 C15 C14 -176.20(11) . . . . ?
C10 C11 C12 C13 0.45(18) . . . . ?
C11 C10 C15 C14 1.88(17) . . . . ?
C11 C12 C13 C14 1.17(18) . . . . ?
C11 C12 C13 C16 -177.77(11) . . . . ?
C12 C13 C14 C15 -1.26(18) . . . . ?
C13 C14 C15 C10 -0.27(18) . . . . ?
C15 C10 C11 C12 -1.97(17) . . . . ?
C16 C13 C14 C15 177.67(11) . . . . ?
C17 C6 C7 C8 -179.23(10) . . . . ?
C17 C18 C19 C20 0.44(18) . . . . ?
C18 C17 C22 C21 1.53(17) . . . . ?
C18 C19 C20 C21 0.86(18) . . . . ?
C18 C19 C20 C23 -178.68(11) . . . . ?
C19 C20 C21 C22 -0.96(18) . . . . ?
C20 C21 C22 C17 -0.24(18) . . . . ?
C22 C17 C18 C19 -1.62(17) . . . . ?
C23 C20 C21 C22 178.59(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
####################################################################### 
# 
# 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_8v00374_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2179270'
loop_
_audit_author_name
_audit_author_address
'Georgina Rosair'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_audit_creation_date             2022-06-14
_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         'C30 H20 N2 S'
_chemical_formula_sum            'C30 H20 N2 S'
_chemical_formula_weight         440.54
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.0869(2)
_cell_length_b                   13.0076(2)
_cell_length_c                   12.0906(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.0421(5)
_cell_angle_gamma                90
_cell_volume                     2139.53(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      74.450
_cell_measurement_theta_min      4.704
_shelx_estimated_absorpt_T_max   0.864
_shelx_estimated_absorpt_T_min   0.614
_exptl_absorpt_coefficient_mu    1.501
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1171 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.8412.
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    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17484
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.442
_diffrn_reflns_theta_min         4.703
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_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
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2131
_reflns_number_total             2160
_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 V8.40A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 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         0.270
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.070
_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)+(0.0363P)²+2.0847P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0811
_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:
 C9(H9), C8(H8), C16(H16), C13(H13), C17(H17), C7(H7), C5(H5), C15(H15),
 C10(H10), C14(H14)
;
_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 0.500000 0.09981(3) 0.250000 0.02064(13) Uani 1 2 d S T P . .
N2 N 0.45093(7) 0.17845(7) 0.32280(8) 0.0181(2) Uani 1 1 d . . . . .
C3 C 0.47286(8) 0.27360(9) 0.29302(9) 0.0147(2) Uani 1 1 d . . . . .
C11 C 0.42262(8) 0.31341(9) 0.53206(10) 0.0162(2) Uani 1 1 d . . . . .
C6 C 0.39219(8) 0.36962(9) 0.42924(9) 0.0156(2) Uani 1 1 d . . . . .
C9 C 0.27727(9) 0.37088(10) 0.58703(10) 0.0207(3) Uani 1 1 d . . . . .
H9 H 0.237299 0.369366 0.639349 0.025 Uiso 1 1 calc R U . . .
C12 C 0.51952(8) 0.26047(9) 0.56599(9) 0.0165(2) Uani 1 1 d . . . . .
C8 C 0.24988(9) 0.43016(9) 0.48815(10) 0.0198(3) Uani 1 1 d . . . . .
H8 H 0.192563 0.471761 0.474345 0.024 Uiso 1 1 calc R U . . .
C16 C 0.69666(9) 0.26766(10) 0.60199(10) 0.0207(3) Uani 1 1 d . . . . .
H16 H 0.754498 0.305827 0.603572 0.025 Uiso 1 1 calc R U . . .
C13 C 0.52756(9) 0.15856(10) 0.60396(10) 0.0205(3) Uani 1 1 d . . . . .
H13 H 0.470158 0.121480 0.606858 0.025 Uiso 1 1 calc R U . . .
C17 C 0.60530(9) 0.31393(9) 0.56490(9) 0.0179(2) Uani 1 1 d . . . . .
H17 H 0.600924 0.382948 0.538365 0.021 Uiso 1 1 calc R U . . .
C7 C 0.30623(8) 0.42851(9) 0.40982(10) 0.0180(2) Uani 1 1 d . . . . .
H7 H 0.286200 0.468045 0.341661 0.022 Uiso 1 1 calc R U . . .
C4 C 0.44727(8) 0.36795(9) 0.33942(9) 0.0152(2) Uani 1 1 d . . . . .
C5 C 0.47439(8) 0.45623(9) 0.29375(9) 0.0175(2) Uani 1 1 d . . . . .
H5 H 0.458326 0.520446 0.321672 0.021 Uiso 1 1 calc R U . . .
C15 C 0.70379(9) 0.16562(10) 0.63683(10) 0.0230(3) Uani 1 1 d . . . . .
H15 H 0.766218 0.133143 0.660093 0.028 Uiso 1 1 calc R U . . .
C10 C 0.36351(9) 0.31389(9) 0.60874(10) 0.0192(2) Uani 1 1 d . . . . .
H10 H 0.382698 0.274452 0.677049 0.023 Uiso 1 1 calc R U . . .
C14 C 0.61875(9) 0.11120(10) 0.63742(11) 0.0233(3) Uani 1 1 d . . . . .
H14 H 0.623249 0.041272 0.660877 0.028 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 N2 1.6170(10) . ?
S1 N2 1.6170(10) 2_655 ?
N2 C3 1.3471(15) . ?
C3 C3 1.442(2) 2_655 ?
C3 C4 1.4339(15) . ?
C11 C6 1.4096(16) . ?
C11 C12 1.4883(16) . ?
C11 C10 1.3978(15) . ?
C6 C7 1.4001(16) . ?
C6 C4 1.4899(15) . ?
C9 H9 0.9500 . ?
C9 C8 1.3905(18) . ?
C9 C10 1.3887(17) . ?
C12 C13 1.3978(17) . ?
C12 C17 1.3971(16) . ?
C8 H8 0.9500 . ?
C8 C7 1.3849(16) . ?
C16 H16 0.9500 . ?
C16 C17 1.3857(17) . ?
C16 C15 1.3883(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.3870(17) . ?
C17 H17 0.9500 . ?
C7 H7 0.9500 . ?
C4 C5 1.3707(16) . ?
C5 C5 1.427(2) 2_655 ?
C5 H5 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.3931(18) . ?
C10 H10 0.9500 . ?
C14 H14 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 N2 101.51(7) . 2_655 ?
C3 N2 S1 106.00(7) . . ?
N2 C3 C3 113.21(6) . 2_655 ?
N2 C3 C4 125.69(10) . . ?
C4 C3 C3 121.10(6) . 2_655 ?
C6 C11 C12 122.03(10) . . ?
C10 C11 C6 119.04(11) . . ?
C10 C11 C12 118.74(10) . . ?
C11 C6 C4 122.58(10) . . ?
C7 C6 C11 118.92(10) . . ?
C7 C6 C4 118.50(10) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C10 C9 C8 119.51(11) . . ?
C13 C12 C11 121.31(10) . . ?
C17 C12 C11 120.05(10) . . ?
C17 C12 C13 118.59(11) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 119.93(11) . . ?
C7 C8 H8 120.0 . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.09(11) . . ?
C15 C16 H16 120.0 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.46(11) . . ?
C14 C13 H13 119.8 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 120.91(11) . . ?
C16 C17 H17 119.5 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.20(11) . . ?
C8 C7 H7 119.4 . . ?
C3 C4 C6 121.95(10) . . ?
C5 C4 C3 115.77(10) . . ?
C5 C4 C6 122.26(10) . . ?
C4 C5 C5 123.10(7) . 2_655 ?
C4 C5 H5 118.5 . . ?
C5 C5 H5 118.5 2_655 . ?
C16 C15 H15 120.2 . . ?
C16 C15 C14 119.52(11) . . ?
C14 C15 H15 120.2 . . ?
C11 C10 H10 119.4 . . ?
C9 C10 C11 121.30(11) . . ?
C9 C10 H10 119.4 . . ?
C13 C14 C15 120.36(12) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?

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 N2 C3 C3 2.08(14) . . . 2_655 ?
S1 N2 C3 C4 -177.65(9) . . . . ?
N2 S1 N2 C3 -0.78(5) 2_655 . . . ?
N2 C3 C4 C6 0.38(17) . . . . ?
N2 C3 C4 C5 -177.95(11) . . . . ?
C3 C3 C4 C6 -179.33(12) 2_655 . . . ?
C3 C3 C4 C5 2.34(18) 2_655 . . . ?
C3 C4 C5 C5 -0.5(2) . . . 2_655 ?
C11 C6 C7 C8 -1.67(17) . . . . ?
C11 C6 C4 C3 52.66(15) . . . . ?
C11 C6 C4 C5 -129.12(12) . . . . ?
C11 C12 C13 C14 -178.68(11) . . . . ?
C11 C12 C17 C16 176.53(10) . . . . ?
C6 C11 C12 C13 -132.15(12) . . . . ?
C6 C11 C12 C17 50.56(15) . . . . ?
C6 C11 C10 C9 -1.90(17) . . . . ?
C6 C4 C5 C5 -178.85(13) . . . 2_655 ?
C9 C8 C7 C6 -1.40(17) . . . . ?
C12 C11 C6 C7 -171.68(10) . . . . ?
C12 C11 C6 C4 9.08(16) . . . . ?
C12 C11 C10 C9 173.22(10) . . . . ?
C12 C13 C14 C15 1.91(18) . . . . ?
C8 C9 C10 C11 -1.16(18) . . . . ?
C16 C15 C14 C13 -0.27(19) . . . . ?
C13 C12 C17 C16 -0.83(16) . . . . ?
C17 C12 C13 C14 -1.36(17) . . . . ?
C17 C16 C15 C14 -1.90(17) . . . . ?
C7 C6 C4 C3 -126.58(12) . . . . ?
C7 C6 C4 C5 51.64(15) . . . . ?
C4 C6 C7 C8 177.60(10) . . . . ?
C15 C16 C17 C12 2.47(17) . . . . ?
C10 C11 C6 C7 3.27(16) . . . . ?
C10 C11 C6 C4 -175.97(10) . . . . ?
C10 C11 C12 C13 52.88(15) . . . . ?
C10 C11 C12 C17 -124.41(12) . . . . ?
C10 C9 C8 C7 2.81(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
####################################################################### 
# 
# 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_8v00384_0m
_database_code_depnum_ccdc_archive 'CCDC 2179273'
loop_
_audit_author_name
_audit_author_address
'Georgina Rosair'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT250_cu_8v00384_0m       
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.6 Note
RESPONSE: C/S substitutional disorder  (S8 C15 92% ) in 5 membered ring 
;
# Added during the CSD deposition process: Wednesday 15 June 2022 11:33 AM
# end Validation Reply Form

_audit_creation_date             2022-06-09
_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         'C22 H12 N2 S3'
_chemical_formula_sum            'C22 H12 N2 S3'
_chemical_formula_weight         400.52
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.8527(3)
_cell_length_b                   18.2496(11)
_cell_length_c                   24.0476(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1690.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6247
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      74.607
_cell_measurement_theta_min      3.039
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.321
_exptl_absorpt_coefficient_mu    4.079
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1393 before and 0.0845 after correction.
The Ratio of minimum to maximum transmission is 0.5609.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.36
_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  0.0732
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11269
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.624
_diffrn_reflns_theta_min         3.040
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_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
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                3130
_reflns_number_total             3403
_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 V8.40A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 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         0.507
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 
;
 Flack x determined using 1087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.093
_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)+(0.0205P)²+5.0708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1408
_refine_special_details          disorder
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{C15, S15}
{S8, C8}
3. Uiso/Uaniso restraints and constraints
Uanis(C15) = Uanis(S15)
Uanis(S8) = Uanis(C8)
4. Others
 Sof(S15)=Sof(C8)=Sof(H8)=1-FVAR(1)
 Sof(S8)=Sof(C15)=Sof(H15)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C19(H19), C20(H20),
 C21(H21), C22(H22), C24(H24), C15(H15), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.7126(4) 0.51979(8) 0.70919(6) 0.0245(4) Uani 1 1 d . . . . .
S8 S 0.2007(4) 0.65281(8) 0.48144(7) 0.0239(5) Uani 0.918(8) 1 d . . P A 3
S17 S 0.0297(4) 0.82599(8) 0.76353(7) 0.0258(4) Uani 1 1 d . . . . .
N1 N 0.6270(14) 0.5359(3) 0.6446(2) 0.0239(12) Uani 1 1 d . . . . .
N2 N 0.5671(14) 0.5933(3) 0.7384(2) 0.0242(11) Uani 1 1 d . . . . .
C1 C 0.4766(17) 0.6029(3) 0.6430(2) 0.0223(12) Uani 1 1 d . . . . .
C2 C 0.4403(16) 0.6357(3) 0.6970(3) 0.0222(12) Uani 1 1 d . . . . .
C3 C 0.2825(16) 0.7064(3) 0.7037(3) 0.0229(12) Uani 1 1 d . . . . .
C4 C 0.1778(17) 0.7396(3) 0.6551(3) 0.0238(13) Uani 1 1 d . . . . .
H4 H 0.075202 0.786816 0.657522 0.029 Uiso 1 1 calc R U . . .
C5 C 0.2136(18) 0.7076(3) 0.6020(3) 0.0243(13) Uani 1 1 d . . . . .
H5 H 0.136239 0.734542 0.570576 0.029 Uiso 1 1 calc R U . . .
C6 C 0.3554(16) 0.6392(3) 0.5937(3) 0.0249(13) Uani 1 1 d . . . . .
C7 C 0.3703(15) 0.6050(4) 0.5386(3) 0.0218(13) Uani 1 1 d . . . . .
C9 C 0.3029(18) 0.5819(3) 0.4369(3) 0.0265(13) Uani 1 1 d . . . . .
C10 C 0.2394(19) 0.5788(4) 0.3790(3) 0.0309(15) Uani 1 1 d . . . . .
H10 H 0.128300 0.618158 0.360219 0.037 Uiso 1 1 calc R U . . .
C11 C 0.3445(19) 0.5166(4) 0.3507(3) 0.0384(18) Uani 1 1 d . . . . .
H11 H 0.306556 0.513518 0.311747 0.046 Uiso 1 1 calc R U . . .
C12 C 0.5048(19) 0.4585(4) 0.3782(3) 0.0347(16) Uani 1 1 d . . . . .
H12 H 0.575672 0.416480 0.357751 0.042 Uiso 1 1 calc R U . . .
C13 C 0.5607(19) 0.4614(4) 0.4341(3) 0.0327(15) Uani 1 1 d . . . . .
H13 H 0.665986 0.421006 0.452464 0.039 Uiso 1 1 calc R U . . .
C14 C 0.4640(16) 0.5236(3) 0.4649(3) 0.0238(13) Uani 1 1 d . . . . .
C15 C 0.5072(16) 0.5351(3) 0.5244(2) 0.0363(19) Uani 0.918(8) 1 d . . P A 1
H15 H 0.609955 0.501393 0.549632 0.044 Uiso 0.918(8) 1 calc R U P A 1
C16 C 0.2246(16) 0.7388(3) 0.7586(3) 0.0242(12) Uani 1 1 d . . . . .
C18 C 0.0455(17) 0.8240(4) 0.8357(3) 0.0257(13) Uani 1 1 d . . . . .
C19 C -0.0718(17) 0.8770(4) 0.8728(3) 0.0281(14) Uani 1 1 d . . . . .
H19 H -0.179102 0.920598 0.859625 0.034 Uiso 1 1 calc R U . . .
C20 C -0.0292(19) 0.8651(4) 0.9286(3) 0.0328(15) Uani 1 1 d . . . . .
H20 H -0.108901 0.900788 0.954331 0.039 Uiso 1 1 calc R U . . .
C21 C 0.1297(17) 0.8012(4) 0.9482(3) 0.0290(15) Uani 1 1 d . . . . .
H21 H 0.162342 0.794701 0.987066 0.035 Uiso 1 1 calc R U . . .
C22 C 0.2390(18) 0.7478(3) 0.9119(3) 0.0260(13) Uani 1 1 d . . . . .
H22 H 0.340988 0.704031 0.925705 0.031 Uiso 1 1 calc R U . . .
C23 C 0.1995(16) 0.7582(3) 0.8550(3) 0.0229(12) Uani 1 1 d . . . . .
C24 C 0.3018(17) 0.7103(3) 0.8100(2) 0.0241(12) Uani 1 1 d . . . . .
H24 H 0.410647 0.664118 0.815330 0.029 Uiso 1 1 calc R U . . .
S15 S 0.5072(16) 0.5351(3) 0.5244(2) 0.0363(19) Uani 0.082(8) 1 d . . P A 2
C8 C 0.2007(4) 0.65281(8) 0.48144(7) 0.0239(5) Uani 0.082(8) 1 d . . P A 4
H8 H 0.094559 0.699400 0.476825 0.029 Uiso 0.082(8) 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 N1 1.616(5) . ?
S1 N2 1.615(5) . ?
S8 C7 1.754(6) . ?
S8 C9 1.725(7) . ?
S17 C16 1.763(6) . ?
S17 C18 1.737(6) . ?
N1 C1 1.354(8) . ?
N2 C2 1.353(8) . ?
C1 C2 1.436(9) . ?
C1 C6 1.437(9) . ?
C2 C3 1.435(8) . ?
C3 C4 1.375(9) . ?
C3 C16 1.463(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.411(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(9) . ?
C6 C7 1.467(9) . ?
C7 C15 1.422(9) . ?
C7 S15 1.422(9) . ?
C7 C8 1.754(6) . ?
C9 C10 1.415(9) . ?
C9 C14 1.403(9) . ?
C9 C8 1.725(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(11) . ?
C11 H11 0.9500 . ?
C11 C12 1.395(11) . ?
C12 H12 0.9500 . ?
C12 C13 1.363(10) . ?
C13 H13 0.9500 . ?
C13 C14 1.405(9) . ?
C14 C15 1.456(9) . ?
C14 S15 1.456(9) . ?
C15 H15 0.9500 . ?
C16 C24 1.374(9) . ?
C18 C19 1.391(9) . ?
C18 C23 1.418(9) . ?
C19 H19 0.9500 . ?
C19 C20 1.369(10) . ?
C20 H20 0.9500 . ?
C20 C21 1.399(10) . ?
C21 H21 0.9500 . ?
C21 C22 1.374(9) . ?
C22 H22 0.9500 . ?
C22 C23 1.391(9) . ?
C23 C24 1.446(8) . ?
C24 H24 0.9500 . ?
C8 H8 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 101.4(3) . . ?
C9 S8 C7 91.6(3) . . ?
C18 S17 C16 92.0(3) . . ?
C1 N1 S1 106.1(4) . . ?
C2 N2 S1 106.2(4) . . ?
N1 C1 C2 113.2(5) . . ?
N1 C1 C6 125.3(6) . . ?
C2 C1 C6 121.5(6) . . ?
N2 C2 C1 113.1(5) . . ?
N2 C2 C3 125.8(6) . . ?
C3 C2 C1 121.2(5) . . ?
C2 C3 C16 121.9(5) . . ?
C4 C3 C2 115.1(5) . . ?
C4 C3 C16 122.9(6) . . ?
C3 C4 H4 118.1 . . ?
C3 C4 C5 123.9(6) . . ?
C5 C4 H4 118.1 . . ?
C4 C5 H5 118.5 . . ?
C6 C5 C4 123.1(6) . . ?
C6 C5 H5 118.5 . . ?
C1 C6 C7 122.5(5) . . ?
C5 C6 C1 115.2(6) . . ?
C5 C6 C7 122.2(6) . . ?
C6 C7 S8 118.8(5) . . ?
C6 C7 C8 118.8(5) . . ?
C15 C7 C6 127.8(6) . . ?
S15 C7 C6 127.8(6) . . ?
C10 C9 S8 126.9(5) . . ?
C10 C9 C8 126.9(5) . . ?
C14 C9 S8 111.9(5) . . ?
C14 C9 C10 121.2(6) . . ?
C14 C9 C8 111.9(5) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 C9 117.8(7) . . ?
C11 C10 H10 121.1 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.4(7) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(7) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(7) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 C13 118.5(6) . . ?
C9 C14 C15 114.4(6) . . ?
C9 C14 S15 114.4(6) . . ?
C13 C14 C15 127.1(6) . . ?
C13 C14 S15 127.1(6) . . ?
C7 C15 C14 108.8(6) . . ?
C7 C15 H15 125.6 . . ?
C14 C15 H15 125.6 . . ?
C3 C16 S17 119.4(4) . . ?
C24 C16 S17 111.9(5) . . ?
C24 C16 C3 128.7(6) . . ?
C19 C18 S17 127.9(5) . . ?
C19 C18 C23 121.1(6) . . ?
C23 C18 S17 111.0(5) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 C18 118.6(6) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.1(6) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.7(6) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.7(6) . . ?
C23 C22 H22 120.2 . . ?
C18 C23 C24 112.4(6) . . ?
C22 C23 C18 118.9(6) . . ?
C22 C23 C24 128.7(6) . . ?
C16 C24 C23 112.7(6) . . ?
C16 C24 H24 123.7 . . ?
C23 C24 H24 123.7 . . ?
C7 S15 C14 108.8(6) . . ?
C7 C8 H8 134.2 . . ?
C9 C8 C7 91.6(3) . . ?
C9 C8 H8 134.2 . . ?

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 -0.7(7) . . . . ?
S1 N1 C1 C6 -179.6(5) . . . . ?
S1 N2 C2 C1 -0.2(6) . . . . ?
S1 N2 C2 C3 179.6(5) . . . . ?
S8 C9 C10 C11 179.6(5) . . . . ?
S8 C9 C14 C13 179.6(5) . . . . ?
S17 C16 C24 C23 0.9(7) . . . . ?
S17 C18 C19 C20 -179.0(6) . . . . ?
S17 C18 C23 C22 178.9(5) . . . . ?
S17 C18 C23 C24 -0.1(7) . . . . ?
N1 S1 N2 C2 -0.2(5) . . . . ?
N1 C1 C2 N2 0.6(8) . . . . ?
N1 C1 C2 C3 -179.2(5) . . . . ?
N1 C1 C6 C5 -179.4(6) . . . . ?
N1 C1 C6 C7 2.6(10) . . . . ?
N2 S1 N1 C1 0.6(5) . . . . ?
N2 C2 C3 C4 179.1(6) . . . . ?
N2 C2 C3 C16 -3.5(9) . . . . ?
C1 C2 C3 C4 -1.1(8) . . . . ?
C1 C2 C3 C16 176.3(6) . . . . ?
C1 C6 C7 S8 177.7(5) . . . . ?
C1 C6 C7 C15 -1.9(10) . . . . ?
C1 C6 C7 S15 -1.9(10) . . . . ?
C1 C6 C7 C8 177.7(5) . . . . ?
C2 C1 C6 C5 1.8(9) . . . . ?
C2 C1 C6 C7 -176.2(6) . . . . ?
C2 C3 C4 C5 1.0(9) . . . . ?
C2 C3 C16 S17 179.9(4) . . . . ?
C2 C3 C16 C24 -0.3(10) . . . . ?
C3 C4 C5 C6 0.6(11) . . . . ?
C3 C16 C24 C23 -178.9(6) . . . . ?
C4 C3 C16 S17 -2.9(9) . . . . ?
C4 C3 C16 C24 176.9(7) . . . . ?
C4 C5 C6 C1 -1.9(9) . . . . ?
C4 C5 C6 C7 176.0(6) . . . . ?
C5 C6 C7 S8 -0.1(8) . . . . ?
C5 C6 C7 C15 -179.7(6) . . . . ?
C5 C6 C7 S15 -179.7(6) . . . . ?
C5 C6 C7 C8 -0.1(8) . . . . ?
C6 C1 C2 N2 179.6(6) . . . . ?
C6 C1 C2 C3 -0.3(9) . . . . ?
C6 C7 C15 C14 179.5(6) . . . . ?
C6 C7 S15 C14 179.5(6) . . . . ?
C6 C7 C8 C9 -179.3(5) . . . . ?
C7 S8 C9 C10 179.4(6) . . . . ?
C7 S8 C9 C14 -0.4(5) . . . . ?
C9 S8 C7 C6 -179.3(5) . . . . ?
C9 C10 C11 C12 0.6(10) . . . . ?
C9 C14 C15 C7 -0.2(7) . . . . ?
C9 C14 S15 C7 -0.2(7) . . . . ?
C10 C9 C14 C13 -0.3(10) . . . . ?
C10 C9 C14 C15 -179.4(6) . . . . ?
C10 C9 C14 S15 -179.4(6) . . . . ?
C10 C9 C8 C7 179.4(6) . . . . ?
C10 C11 C12 C13 0.3(11) . . . . ?
C11 C12 C13 C14 -1.3(11) . . . . ?
C12 C13 C14 C9 1.2(10) . . . . ?
C12 C13 C14 C15 -179.8(6) . . . . ?
C12 C13 C14 S15 -179.8(6) . . . . ?
C13 C14 C15 C7 -179.2(6) . . . . ?
C13 C14 S15 C7 -179.2(6) . . . . ?
C14 C9 C10 C11 -0.6(10) . . . . ?
C14 C9 C8 C7 -0.4(5) . . . . ?
C16 S17 C18 C19 -179.3(6) . . . . ?
C16 S17 C18 C23 0.5(5) . . . . ?
C16 C3 C4 C5 -176.4(6) . . . . ?
C18 S17 C16 C3 179.0(5) . . . . ?
C18 S17 C16 C24 -0.8(5) . . . . ?
C18 C19 C20 C21 0.2(10) . . . . ?
C18 C23 C24 C16 -0.5(8) . . . . ?
C19 C18 C23 C22 -1.3(10) . . . . ?
C19 C18 C23 C24 179.7(6) . . . . ?
C19 C20 C21 C22 -1.7(10) . . . . ?
C20 C21 C22 C23 1.7(10) . . . . ?
C21 C22 C23 C18 -0.2(10) . . . . ?
C21 C22 C23 C24 178.6(6) . . . . ?
C22 C23 C24 C16 -179.4(7) . . . . ?
C23 C18 C19 C20 1.3(10) . . . . ?
C8 C9 C10 C11 179.6(5) . . . . ?
C8 C9 C14 C13 179.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
####################################################################### 
# 
# 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_8v00376_0m
_database_code_depnum_ccdc_archive 'CCDC 2179271'
loop_
_audit_author_name
_audit_author_address
'Georgina Rosair'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_audit_creation_date             2022-06-13
_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         'C30 H20 N2 S'
_chemical_formula_sum            'C30 H20 N2 S'
_chemical_formula_weight         440.54
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0161(2)
_cell_length_b                   10.5126(2)
_cell_length_c                   10.5965(2)
_cell_angle_alpha                90.8070(10)
_cell_angle_beta                 98.9060(10)
_cell_angle_gamma                104.3010(10)
_cell_volume                     1066.55(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9857
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      71.786
_cell_measurement_theta_min      4.229
_shelx_estimated_absorpt_T_max   0.864
_shelx_estimated_absorpt_T_min   0.733
_exptl_absorpt_coefficient_mu    1.505
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0902 before and 0.0647 after correction.
The Ratio of minimum to maximum transmission is 0.8670.
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    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            47343
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.247
_diffrn_reflns_theta_min         4.229
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3535
_reflns_number_total             4204
_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 V8.40A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.054
_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     298
_refine_ls_number_reflns         4204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0385
_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)+(0.0457P)²+0.5710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0993
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30)
;
_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 0.48863(4) 0.63200(4) 0.30448(4) 0.02167(12) Uani 1 1 d . . . . .
N1 N 0.40655(14) 0.47969(13) 0.30901(13) 0.0197(3) Uani 1 1 d . . . . .
N2 N 0.43832(14) 0.69910(13) 0.42014(13) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.12955(16) -0.27031(16) 0.26717(16) 0.0209(3) Uani 1 1 d . . . . .
H1 H 0.112099 -0.262757 0.352208 0.025 Uiso 1 1 calc R U . . .
C2 C 0.11754(17) -0.39372(16) 0.21155(17) 0.0231(4) Uani 1 1 d . . . . .
H2 H 0.091358 -0.469672 0.258541 0.028 Uiso 1 1 calc R U . . .
C3 C 0.14345(18) -0.40704(17) 0.08800(18) 0.0262(4) Uani 1 1 d . . . . .
H3 H 0.136856 -0.491512 0.050661 0.031 Uiso 1 1 calc R U . . .
C4 C 0.17917(19) -0.29556(18) 0.01932(18) 0.0281(4) Uani 1 1 d . . . . .
H4 H 0.195621 -0.303839 -0.065970 0.034 Uiso 1 1 calc R U . . .
C5 C 0.19092(18) -0.17198(17) 0.07489(17) 0.0245(4) Uani 1 1 d . . . . .
H5 H 0.215689 -0.096543 0.026883 0.029 Uiso 1 1 calc R U . . .
C6 C 0.16708(16) -0.15645(16) 0.19972(16) 0.0200(3) Uani 1 1 d . . . . .
C7 C 0.18355(16) -0.02404(15) 0.26103(16) 0.0188(3) Uani 1 1 d . . . . .
C8 C 0.20910(18) -0.00352(16) 0.39416(16) 0.0222(4) Uani 1 1 d . . . . .
H8 H 0.215424 -0.075414 0.446081 0.027 Uiso 1 1 calc R U . . .
C9 C 0.22536(17) 0.11954(16) 0.45177(16) 0.0218(4) Uani 1 1 d . . . . .
H9 H 0.240024 0.130220 0.542447 0.026 Uiso 1 1 calc R U . . .
C10 C 0.22055(16) 0.22799(15) 0.37877(15) 0.0183(3) Uani 1 1 d . . . . .
C11 C 0.19645(16) 0.20886(16) 0.24586(16) 0.0200(3) Uani 1 1 d . . . . .
H11 H 0.193268 0.281610 0.194324 0.024 Uiso 1 1 calc R U . . .
C12 C 0.17708(16) 0.08514(16) 0.18789(16) 0.0199(3) Uani 1 1 d . . . . .
H12 H 0.159131 0.074117 0.097192 0.024 Uiso 1 1 calc R U . . .
C13 C 0.24008(16) 0.35901(15) 0.44257(15) 0.0189(3) Uani 1 1 d . . . . .
C14 C 0.33144(16) 0.47505(15) 0.40542(15) 0.0177(3) Uani 1 1 d . . . . .
C15 C 0.35075(16) 0.60065(16) 0.47006(15) 0.0184(3) Uani 1 1 d . . . . .
C16 C 0.27764(16) 0.61458(16) 0.57352(15) 0.0188(3) Uani 1 1 d . . . . .
C17 C 0.19129(17) 0.50090(16) 0.60628(16) 0.0208(3) Uani 1 1 d . . . . .
H17 H 0.141127 0.505838 0.674525 0.025 Uiso 1 1 calc R U . . .
C18 C 0.17361(17) 0.37701(16) 0.54321(16) 0.0205(3) Uani 1 1 d . . . . .
H18 H 0.112853 0.302552 0.571724 0.025 Uiso 1 1 calc R U . . .
C19 C 0.29065(17) 0.74333(15) 0.63940(15) 0.0188(3) Uani 1 1 d . . . . .
C20 C 0.41936(17) 0.83555(16) 0.67221(16) 0.0217(3) Uani 1 1 d . . . . .
H20 H 0.501005 0.817630 0.648908 0.026 Uiso 1 1 calc R U . . .
C21 C 0.42869(17) 0.95312(16) 0.73860(16) 0.0219(4) Uani 1 1 d . . . . .
H21 H 0.517033 1.014399 0.760518 0.026 Uiso 1 1 calc R U . . .
C22 C 0.31059(17) 0.98300(15) 0.77377(15) 0.0183(3) Uani 1 1 d . . . . .
C23 C 0.18133(17) 0.89233(16) 0.73750(16) 0.0206(3) Uani 1 1 d . . . . .
H23 H 0.099148 0.911897 0.757666 0.025 Uiso 1 1 calc R U . . .
C24 C 0.17188(17) 0.77421(15) 0.67242(15) 0.0193(3) Uani 1 1 d . . . . .
H24 H 0.083381 0.713285 0.649910 0.023 Uiso 1 1 calc R U . . .
C25 C 0.32136(17) 1.10758(15) 0.84738(15) 0.0189(3) Uani 1 1 d . . . . .
C26 C 0.43821(17) 1.16166(16) 0.94070(16) 0.0216(3) Uani 1 1 d . . . . .
H26 H 0.510410 1.117261 0.957934 0.026 Uiso 1 1 calc R U . . .
C27 C 0.44992(18) 1.27881(16) 1.00810(16) 0.0234(4) Uani 1 1 d . . . . .
H27 H 0.529692 1.313864 1.071109 0.028 Uiso 1 1 calc R U . . .
C28 C 0.34572(18) 1.34516(16) 0.98402(16) 0.0235(4) Uani 1 1 d . . . . .
H28 H 0.354797 1.426498 1.028920 0.028 Uiso 1 1 calc R U . . .
C29 C 0.22784(18) 1.29172(16) 0.89365(16) 0.0225(4) Uani 1 1 d . . . . .
H29 H 0.155407 1.335994 0.877765 0.027 Uiso 1 1 calc R U . . .
C30 C 0.21558(17) 1.17392(16) 0.82655(16) 0.0205(3) Uani 1 1 d . . . . .
H30 H 0.134187 1.137888 0.765627 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 1.6144(14) . ?
S1 N2 1.6112(14) . ?
N1 C14 1.354(2) . ?
N2 C15 1.353(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.387(2) . ?
C1 C6 1.404(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(2) . ?
C6 C7 1.488(2) . ?
C7 C8 1.398(2) . ?
C7 C12 1.403(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(2) . ?
C10 C11 1.395(2) . ?
C10 C13 1.481(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.433(2) . ?
C13 C18 1.376(2) . ?
C14 C15 1.434(2) . ?
C15 C16 1.434(2) . ?
C16 C17 1.375(2) . ?
C16 C19 1.481(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.414(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.399(2) . ?
C19 C24 1.400(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.398(2) . ?
C22 C23 1.399(2) . ?
C22 C25 1.487(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.387(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.403(2) . ?
C25 C30 1.398(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.385(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.387(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.391(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.388(2) . ?
C30 H30 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 101.66(7) . . ?
C14 N1 S1 105.85(11) . . ?
C15 N2 S1 106.10(11) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C6 121.01(16) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.50(16) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.27(16) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.23(17) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.32(16) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 120.79(15) . . ?
C5 C6 C1 117.65(15) . . ?
C5 C6 C7 121.54(15) . . ?
C8 C7 C6 120.98(15) . . ?
C8 C7 C12 117.54(15) . . ?
C12 C7 C6 121.47(15) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.26(15) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.99(15) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 118.21(15) . . ?
C9 C10 C13 120.02(14) . . ?
C11 C10 C13 121.77(14) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 120.91(15) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.06(15) . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C10 122.34(14) . . ?
C18 C13 C10 122.14(14) . . ?
C18 C13 C14 115.51(14) . . ?
N1 C14 C13 125.28(14) . . ?
N1 C14 C15 113.30(14) . . ?
C13 C14 C15 121.42(14) . . ?
N2 C15 C14 113.09(14) . . ?
N2 C15 C16 125.94(15) . . ?
C16 C15 C14 120.94(14) . . ?
C15 C16 C19 122.55(14) . . ?
C17 C16 C15 115.79(14) . . ?
C17 C16 C19 121.65(14) . . ?
C16 C17 H17 118.4 . . ?
C16 C17 C18 123.12(15) . . ?
C18 C17 H17 118.4 . . ?
C13 C18 C17 123.21(15) . . ?
C13 C18 H18 118.4 . . ?
C17 C18 H18 118.4 . . ?
C20 C19 C16 122.00(14) . . ?
C20 C19 C24 118.29(15) . . ?
C24 C19 C16 119.70(14) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.50(15) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 119.4 . . ?
C20 C21 C22 121.27(15) . . ?
C22 C21 H21 119.4 . . ?
C21 C22 C23 118.11(15) . . ?
C21 C22 C25 121.15(14) . . ?
C23 C22 C25 120.73(14) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.74(15) . . ?
C24 C23 H23 119.6 . . ?
C19 C24 H24 119.5 . . ?
C23 C24 C19 121.05(15) . . ?
C23 C24 H24 119.5 . . ?
C26 C25 C22 120.74(14) . . ?
C30 C25 C22 121.27(15) . . ?
C30 C25 C26 117.99(15) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 C25 121.01(15) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.30(16) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 120.3 . . ?
C27 C28 C29 119.49(16) . . ?
C29 C28 H28 120.3 . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.26(16) . . ?
C30 C29 H29 119.9 . . ?
C25 C30 H30 119.5 . . ?
C29 C30 C25 120.92(15) . . ?
C29 C30 H30 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C14 C13 178.76(13) . . . . ?
S1 N1 C14 C15 -1.03(16) . . . . ?
S1 N2 C15 C14 -0.62(16) . . . . ?
S1 N2 C15 C16 -178.41(13) . . . . ?
N1 S1 N2 C15 0.01(12) . . . . ?
N1 C14 C15 N2 1.1(2) . . . . ?
N1 C14 C15 C16 179.05(14) . . . . ?
N2 S1 N1 C14 0.61(12) . . . . ?
N2 C15 C16 C17 178.46(15) . . . . ?
N2 C15 C16 C19 0.0(3) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C1 C6 C7 C8 21.8(2) . . . . ?
C1 C6 C7 C12 -159.60(15) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C2 C1 C6 C7 -178.34(15) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C4 C5 C6 C7 178.19(15) . . . . ?
C5 C6 C7 C8 -156.89(16) . . . . ?
C5 C6 C7 C12 21.7(2) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
C6 C7 C8 C9 179.60(15) . . . . ?
C6 C7 C12 C11 -178.17(14) . . . . ?
C7 C8 C9 C10 -1.8(3) . . . . ?
C8 C7 C12 C11 0.5(2) . . . . ?
C8 C9 C10 C11 1.1(2) . . . . ?
C8 C9 C10 C13 -179.19(15) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C9 C10 C13 C14 133.20(17) . . . . ?
C9 C10 C13 C18 -45.5(2) . . . . ?
C10 C11 C12 C7 -1.1(2) . . . . ?
C10 C13 C14 N1 1.4(2) . . . . ?
C10 C13 C14 C15 -178.86(14) . . . . ?
C10 C13 C18 C17 179.54(15) . . . . ?
C11 C10 C13 C14 -47.1(2) . . . . ?
C11 C10 C13 C18 134.16(17) . . . . ?
C12 C7 C8 C9 0.9(2) . . . . ?
C13 C10 C11 C12 -179.38(15) . . . . ?
C13 C14 C15 N2 -178.67(14) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C14 C13 C18 C17 0.7(2) . . . . ?
C14 C15 C16 C17 0.8(2) . . . . ?
C14 C15 C16 C19 -177.62(14) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C15 C16 C19 C20 -42.4(2) . . . . ?
C15 C16 C19 C24 138.73(16) . . . . ?
C16 C17 C18 C13 -0.6(3) . . . . ?
C16 C19 C20 C21 -177.35(15) . . . . ?
C16 C19 C24 C23 178.08(15) . . . . ?
C17 C16 C19 C20 139.25(17) . . . . ?
C17 C16 C19 C24 -39.6(2) . . . . ?
C18 C13 C14 N1 -179.81(15) . . . . ?
C18 C13 C14 C15 0.0(2) . . . . ?
C19 C16 C17 C18 178.30(15) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C20 C19 C24 C23 -0.8(2) . . . . ?
C20 C21 C22 C23 -1.5(2) . . . . ?
C20 C21 C22 C25 178.61(15) . . . . ?
C21 C22 C23 C24 2.2(2) . . . . ?
C21 C22 C25 C26 -35.5(2) . . . . ?
C21 C22 C25 C30 144.89(16) . . . . ?
C22 C23 C24 C19 -1.1(2) . . . . ?
C22 C25 C26 C27 178.92(15) . . . . ?
C22 C25 C30 C29 -178.55(15) . . . . ?
C23 C22 C25 C26 144.64(16) . . . . ?
C23 C22 C25 C30 -35.0(2) . . . . ?
C24 C19 C20 C21 1.5(2) . . . . ?
C25 C22 C23 C24 -177.91(15) . . . . ?
C25 C26 C27 C28 -0.2(3) . . . . ?
C26 C25 C30 C29 1.8(2) . . . . ?
C26 C27 C28 C29 1.4(2) . . . . ?
C27 C28 C29 C30 -1.0(2) . . . . ?
C28 C29 C30 C25 -0.6(2) . . . . ?
C30 C25 C26 C27 -1.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
####################################################################### 
# 
# 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_383dt_0m
_database_code_depnum_ccdc_archive 'CCDC 2179272'
loop_
_audit_author_name
_audit_author_address
'Georgina Rosair'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_audit_creation_date             2020-08-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H16 N2 S'
_chemical_formula_sum            'C26 H16 N2 S'
_chemical_formula_weight         388.47
_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/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                   5.83690(10)
_cell_length_b                   24.3284(6)
_cell_length_c                   13.1740(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.6190(10)
_cell_angle_gamma                90
_cell_volume                     1849.61(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      79.424
_cell_measurement_theta_min      3.634
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.572
_exptl_absorpt_coefficient_mu    1.657
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.5115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1478 before and 0.0858 after correction.
The Ratio of minimum to maximum transmission is 0.6781.
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    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1062
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25819
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.783
_diffrn_reflns_theta_min         3.633
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8Venture'
_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                3368
_reflns_number_total             3978
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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         0.316
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3978
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.057
_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)+(0.0698P)²+1.1082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1358
_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:
 C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), 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 0.25185(9) 0.44975(2) 0.53708(3) 0.02074(15) Uani 1 1 d . . . . .
N1 N 0.1211(3) 0.48419(7) 0.61633(12) 0.0192(3) Uani 1 1 d . . . . .
N2 N 0.3996(3) 0.40649(7) 0.61376(12) 0.0194(3) Uani 1 1 d . . . . .
C1 C 0.1909(3) 0.46240(8) 0.71002(14) 0.0162(4) Uani 1 1 d . . . . .
C2 C 0.3517(3) 0.41780(8) 0.70874(14) 0.0166(4) Uani 1 1 d . . . . .
C3 C 0.4458(3) 0.38986(8) 0.80155(14) 0.0172(4) Uani 1 1 d . . . . .
C4 C 0.3788(3) 0.40961(8) 0.89019(14) 0.0195(4) Uani 1 1 d . . . . .
H4 H 0.437712 0.392279 0.953346 0.023 Uiso 1 1 calc R U . . .
C5 C 0.2255(3) 0.45473(8) 0.89165(14) 0.0200(4) Uani 1 1 d . . . . .
H5 H 0.190355 0.466922 0.956060 0.024 Uiso 1 1 calc R U . . .
C6 C 0.1255(3) 0.48167(8) 0.80458(14) 0.0172(4) Uani 1 1 d . . . . .
C7 C 0.6027(3) 0.34193(8) 0.80212(13) 0.0164(4) Uani 1 1 d . . . . .
C8 C 0.7925(3) 0.34229(8) 0.74559(14) 0.0181(4) Uani 1 1 d . . . . .
H8 H 0.815060 0.372895 0.703393 0.022 Uiso 1 1 calc R U . . .
C9 C 0.9424(3) 0.29883(8) 0.75178(14) 0.0181(4) Uani 1 1 d . . . . .
H9 H 1.069121 0.299813 0.714223 0.022 Uiso 1 1 calc R U . . .
C10 C 0.9120(3) 0.25219(8) 0.81337(13) 0.0165(4) Uani 1 1 d . . . . .
C11 C 1.0643(3) 0.20677(8) 0.82118(14) 0.0182(4) Uani 1 1 d . . . . .
H11 H 1.193495 0.207218 0.785083 0.022 Uiso 1 1 calc R U . . .
C12 C 1.0284(4) 0.16212(8) 0.87999(14) 0.0203(4) Uani 1 1 d . . . . .
H12 H 1.131740 0.131778 0.883780 0.024 Uiso 1 1 calc R U . . .
C13 C 0.8383(4) 0.16086(8) 0.93522(14) 0.0201(4) Uani 1 1 d . . . . .
H13 H 0.815295 0.129889 0.976450 0.024 Uiso 1 1 calc R U . . .
C14 C 0.6876(3) 0.20420(8) 0.92923(14) 0.0185(4) Uani 1 1 d . . . . .
H14 H 0.559993 0.202998 0.966260 0.022 Uiso 1 1 calc R U . . .
C15 C 0.7195(3) 0.25107(8) 0.86827(13) 0.0156(4) Uani 1 1 d . . . . .
C16 C 0.5675(3) 0.29666(8) 0.86083(13) 0.0165(4) Uani 1 1 d . . . . .
H16 H 0.438468 0.296076 0.897039 0.020 Uiso 1 1 calc R U . . .
C17 C -0.0356(3) 0.52840(8) 0.80768(14) 0.0179(4) Uani 1 1 d . . . . .
C18 C -0.2583(3) 0.52782(8) 0.74666(14) 0.0184(4) Uani 1 1 d . . . . .
H18 H -0.300332 0.498231 0.700564 0.022 Uiso 1 1 calc R U . . .
C19 C -0.4124(3) 0.56943(8) 0.75371(14) 0.0176(4) Uani 1 1 d . . . . .
H19 H -0.562498 0.567607 0.714357 0.021 Uiso 1 1 calc R U . . .
C20 C -0.3520(3) 0.61540(7) 0.81889(13) 0.0159(4) Uani 1 1 d . . . . .
C21 C -0.5052(3) 0.65998(8) 0.82468(14) 0.0176(4) Uani 1 1 d . . . . .
H21 H -0.658509 0.658258 0.788443 0.021 Uiso 1 1 calc R U . . .
C22 C -0.4350(3) 0.70552(8) 0.88183(14) 0.0186(4) Uani 1 1 d . . . . .
H22 H -0.538662 0.735474 0.883849 0.022 Uiso 1 1 calc R U . . .
C23 C -0.2085(3) 0.70828(8) 0.93805(14) 0.0190(4) Uani 1 1 d . . . . .
H23 H -0.159987 0.740343 0.976522 0.023 Uiso 1 1 calc R U . . .
C24 C -0.0588(3) 0.66482(8) 0.93716(13) 0.0183(4) Uani 1 1 d . . . . .
H24 H 0.090880 0.666481 0.976988 0.022 Uiso 1 1 calc R U . . .
C25 C -0.1261(3) 0.61733(8) 0.87704(13) 0.0165(4) Uani 1 1 d . . . . .
C26 C 0.0268(3) 0.57251(8) 0.87153(14) 0.0171(4) Uani 1 1 d . . . . .
H26 H 0.175100 0.572882 0.912648 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 1.6165(16) . ?
S1 N2 1.6157(17) . ?
N1 C1 1.349(2) . ?
N2 C2 1.351(2) . ?
C1 C2 1.436(3) . ?
C1 C6 1.435(2) . ?
C2 C3 1.434(3) . ?
C3 C4 1.373(3) . ?
C3 C7 1.482(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.418(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.373(3) . ?
C6 C17 1.480(3) . ?
C7 C8 1.425(2) . ?
C7 C16 1.379(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.367(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.422(3) . ?
C10 C11 1.412(3) . ?
C10 C15 1.425(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.368(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.416(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.368(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.423(3) . ?
C15 C16 1.415(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.422(3) . ?
C17 C26 1.378(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.366(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.422(3) . ?
C20 C21 1.415(3) . ?
C20 C25 1.423(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.367(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.417(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.373(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.422(3) . ?
C25 C26 1.418(3) . ?
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
N2 S1 N1 101.14(8) . . ?
C1 N1 S1 106.27(13) . . ?
C2 N2 S1 106.34(13) . . ?
N1 C1 C2 113.24(16) . . ?
N1 C1 C6 125.63(17) . . ?
C6 C1 C2 121.08(16) . . ?
N2 C2 C1 113.01(16) . . ?
N2 C2 C3 125.96(17) . . ?
C3 C2 C1 121.03(16) . . ?
C2 C3 C7 122.32(16) . . ?
C4 C3 C2 115.96(17) . . ?
C4 C3 C7 121.72(17) . . ?
C3 C4 H4 118.5 . . ?
C3 C4 C5 122.91(18) . . ?
C5 C4 H4 118.5 . . ?
C4 C5 H5 118.4 . . ?
C6 C5 C4 123.26(17) . . ?
C6 C5 H5 118.4 . . ?
C1 C6 C17 121.85(17) . . ?
C5 C6 C1 115.71(17) . . ?
C5 C6 C17 122.42(16) . . ?
C8 C7 C3 121.39(16) . . ?
C16 C7 C3 119.17(16) . . ?
C16 C7 C8 119.42(17) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.32(17) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.21(17) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C15 118.70(17) . . ?
C11 C10 C9 122.35(17) . . ?
C11 C10 C15 118.94(17) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 120.94(17) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.44(18) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.03(17) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.86(17) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C10 118.79(17) . . ?
C16 C15 C10 118.96(17) . . ?
C16 C15 C14 122.25(17) . . ?
C7 C16 C15 121.36(17) . . ?
C7 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C6 120.49(17) . . ?
C26 C17 C6 120.26(18) . . ?
C26 C17 C18 119.23(17) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.61(17) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.19(18) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C25 118.47(17) . . ?
C21 C20 C19 122.29(17) . . ?
C21 C20 C25 119.19(17) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.75(18) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.34(18) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.29(18) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.48(18) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C20 118.87(17) . . ?
C26 C25 C20 119.12(17) . . ?
C26 C25 C24 121.99(18) . . ?
C17 C26 C25 121.28(18) . . ?
C17 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?

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 0.1(2) . . . . ?
S1 N1 C1 C6 177.38(16) . . . . ?
S1 N2 C2 C1 0.4(2) . . . . ?
S1 N2 C2 C3 -179.52(16) . . . . ?
N1 S1 N2 C2 -0.28(15) . . . . ?
N1 C1 C2 N2 -0.3(2) . . . . ?
N1 C1 C2 C3 179.58(17) . . . . ?
N1 C1 C6 C5 -177.24(18) . . . . ?
N1 C1 C6 C17 1.5(3) . . . . ?
N2 S1 N1 C1 0.11(15) . . . . ?
N2 C2 C3 C4 177.77(19) . . . . ?
N2 C2 C3 C7 -3.3(3) . . . . ?
C1 C2 C3 C4 -2.1(3) . . . . ?
C1 C2 C3 C7 176.86(17) . . . . ?
C1 C6 C17 C18 54.8(2) . . . . ?
C1 C6 C17 C26 -126.61(19) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C1 C6 C17 178.56(17) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C2 C3 C7 C8 46.3(3) . . . . ?
C2 C3 C7 C16 -135.45(19) . . . . ?
C3 C4 C5 C6 1.9(3) . . . . ?
C3 C7 C8 C9 176.39(17) . . . . ?
C3 C7 C16 C15 -176.63(17) . . . . ?
C4 C3 C7 C8 -134.8(2) . . . . ?
C4 C3 C7 C16 43.4(3) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
C4 C5 C6 C17 179.48(18) . . . . ?
C5 C6 C17 C18 -126.6(2) . . . . ?
C5 C6 C17 C26 52.0(3) . . . . ?
C6 C1 C2 N2 -177.74(17) . . . . ?
C6 C1 C2 C3 2.2(3) . . . . ?
C6 C17 C18 C19 176.25(16) . . . . ?
C6 C17 C26 C25 -178.97(16) . . . . ?
C7 C3 C4 C5 -178.79(18) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C7 C16 C15 1.7(3) . . . . ?
C8 C9 C10 C11 -179.95(18) . . . . ?
C8 C9 C10 C15 0.7(3) . . . . ?
C9 C10 C11 C12 -179.05(18) . . . . ?
C9 C10 C15 C14 179.43(17) . . . . ?
C9 C10 C15 C16 -0.9(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C10 C15 C16 C7 -0.3(3) . . . . ?
C11 C10 C15 C14 0.1(3) . . . . ?
C11 C10 C15 C16 179.73(16) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C10 -0.1(3) . . . . ?
C13 C14 C15 C16 -179.71(18) . . . . ?
C14 C15 C16 C7 179.36(17) . . . . ?
C15 C10 C11 C12 0.3(3) . . . . ?
C16 C7 C8 C9 -1.9(3) . . . . ?
C17 C18 C19 C20 2.5(3) . . . . ?
C18 C17 C26 C25 -0.4(3) . . . . ?
C18 C19 C20 C21 177.57(17) . . . . ?
C18 C19 C20 C25 0.1(3) . . . . ?
C19 C20 C21 C22 -174.70(16) . . . . ?
C19 C20 C25 C24 175.84(16) . . . . ?
C19 C20 C25 C26 -2.7(2) . . . . ?
C20 C21 C22 C23 -1.3(3) . . . . ?
C20 C25 C26 C17 2.9(3) . . . . ?
C21 C20 C25 C24 -1.7(2) . . . . ?
C21 C20 C25 C26 179.71(15) . . . . ?
C21 C22 C23 C24 -1.2(3) . . . . ?
C22 C23 C24 C25 2.2(3) . . . . ?
C23 C24 C25 C20 -0.7(3) . . . . ?
C23 C24 C25 C26 177.79(16) . . . . ?
C24 C25 C26 C17 -175.65(17) . . . . ?
C25 C20 C21 C22 2.7(3) . . . . ?
C26 C17 C18 C19 -2.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
####################################################################### 
# 
# 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_8v00405_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2179277'
loop_
_audit_author_name
_audit_author_address
'Georgina Rosair'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_audit_creation_date             2022-06-14
_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 H10 I2 N2 S'
_chemical_formula_sum            'C18 H10 I2 N2 S'
_chemical_formula_weight         540.14
_chemical_absolute_configuration ad
_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'
I I -0.3257 6.8362 '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      orthorhombic
_space_group_IT_number           19
_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.00180(10)
_cell_length_b                   11.2976(3)
_cell_length_c                   36.3004(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1641.17(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9740
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      74.645
_cell_measurement_theta_min      2.434
_shelx_estimated_absorpt_T_max   0.573
_shelx_estimated_absorpt_T_min   0.030
_exptl_absorpt_coefficient_mu    31.280
_exptl_absorpt_correction_T_max  0.2697
_exptl_absorpt_correction_T_min  0.0067
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1567 before and 0.0910 after correction.
The Ratio of minimum to maximum transmission is 0.0248.
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    2.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            22058
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.648
_diffrn_reflns_theta_min         2.434
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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                   ?
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3326
_reflns_number_total             3329
_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 V8.40A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 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         1.700
_refine_diff_density_min         -1.341
_refine_diff_density_rms         0.271
_refine_ls_abs_structure_details 
;
 Flack x determined using 1303 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0764P)²+1.2777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.0962
_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:
 C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15),
 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
I1 I 0.09143(11) 0.40566(3) 0.43240(2) 0.02149(16) Uani 1 1 d . . . . .
I2 I 0.95755(11) 0.68096(3) 0.84268(2) 0.02063(16) Uani 1 1 d . . . . .
S1 S 0.1419(5) 0.86774(13) 0.62366(4) 0.0222(4) Uani 1 1 d . . . . .
N1 N 0.1784(18) 0.7604(5) 0.59444(16) 0.0225(12) Uani 1 1 d . . . . .
N2 N 0.3122(16) 0.8101(5) 0.66013(15) 0.0210(12) Uani 1 1 d . . . . .
C1 C 0.3306(18) 0.6725(5) 0.61250(18) 0.0193(13) Uani 1 1 d . . . . .
C2 C 0.4062(19) 0.7004(5) 0.65043(17) 0.0189(12) Uani 1 1 d . . . . .
C3 C 0.5534(18) 0.6142(6) 0.67429(17) 0.0185(12) Uani 1 1 d . . . . .
C4 C 0.612(2) 0.5044(5) 0.65870(19) 0.0227(13) Uani 1 1 d . . . . .
H4 H 0.701022 0.443784 0.673920 0.027 Uiso 1 1 calc R U . . .
C5 C 0.545(2) 0.4773(6) 0.62128(19) 0.0222(13) Uani 1 1 d . . . . .
H5 H 0.599654 0.400677 0.612302 0.027 Uiso 1 1 calc R U . . .
C6 C 0.4059(18) 0.5576(5) 0.59768(18) 0.0182(13) Uani 1 1 d . . . . .
C7 C 0.3306(19) 0.5261(6) 0.55866(18) 0.0190(13) Uani 1 1 d . . . . .
C8 C 0.184(2) 0.4169(5) 0.55128(18) 0.0202(13) Uani 1 1 d . . . . .
H8 H 0.128341 0.365507 0.571069 0.024 Uiso 1 1 calc R U . . .
C9 C 0.1173(19) 0.3822(6) 0.51517(18) 0.0204(13) Uani 1 1 d . . . . .
H9 H 0.015951 0.307863 0.510244 0.024 Uiso 1 1 calc R U . . .
C10 C 0.2011(18) 0.4578(6) 0.48659(17) 0.0191(13) Uani 1 1 d . . . . .
C11 C 0.355(2) 0.5674(6) 0.49311(19) 0.0220(14) Uani 1 1 d . . . . .
H11 H 0.420453 0.616720 0.473195 0.026 Uiso 1 1 calc R U . . .
C12 C 0.4098(19) 0.6023(6) 0.52945(18) 0.0214(13) Uani 1 1 d . . . . .
H12 H 0.501307 0.678179 0.534444 0.026 Uiso 1 1 calc R U . . .
C13 C 0.6323(18) 0.6349(5) 0.71372(18) 0.0198(13) Uani 1 1 d . . . . .
C14 C 0.573(2) 0.5452(6) 0.73969(18) 0.0224(14) Uani 1 1 d . . . . .
H14 H 0.467531 0.473932 0.732019 0.027 Uiso 1 1 calc R U . . .
C15 C 0.665(2) 0.5586(6) 0.7765(2) 0.0237(14) Uani 1 1 d . . . . .
H15 H 0.627686 0.496543 0.793665 0.028 Uiso 1 1 calc R U . . .
C16 C 0.8101(17) 0.6633(6) 0.78759(16) 0.0178(12) Uani 1 1 d . . . . .
C17 C 0.8660(18) 0.7550(6) 0.76272(19) 0.0200(13) Uani 1 1 d . . . . .
H17 H 0.967411 0.826518 0.770716 0.024 Uiso 1 1 calc R U . . .
C18 C 0.773(2) 0.7411(5) 0.72623(19) 0.0208(14) Uani 1 1 d . . . . .
H18 H 0.804268 0.804598 0.709432 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
I1 C10 2.100(6) . ?
I2 C16 2.095(6) . ?
S1 N1 1.618(6) . ?
S1 N2 1.625(6) . ?
N1 C1 1.336(9) . ?
N2 C2 1.343(8) . ?
C1 C2 1.444(9) . ?
C1 C6 1.438(8) . ?
C2 C3 1.430(9) . ?
C3 C4 1.383(9) . ?
C3 C13 1.484(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.417(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.367(9) . ?
C6 C7 1.491(9) . ?
C7 C8 1.392(9) . ?
C7 C12 1.402(9) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(10) . ?
C10 C11 1.403(10) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.405(9) . ?
C13 C18 1.400(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.394(10) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(10) . ?
C16 C17 1.392(9) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(10) . ?
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
N1 S1 N2 101.3(3) . . ?
C1 N1 S1 106.0(5) . . ?
C2 N2 S1 105.9(5) . . ?
N1 C1 C2 113.7(5) . . ?
N1 C1 C6 125.6(6) . . ?
C6 C1 C2 120.6(6) . . ?
N2 C2 C1 113.1(6) . . ?
N2 C2 C3 125.8(6) . . ?
C3 C2 C1 121.0(6) . . ?
C2 C3 C13 124.4(6) . . ?
C4 C3 C2 115.6(6) . . ?
C4 C3 C13 120.0(6) . . ?
C3 C4 H4 118.2 . . ?
C3 C4 C5 123.7(6) . . ?
C5 C4 H4 118.2 . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.2(6) . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C7 121.9(6) . . ?
C5 C6 C1 116.8(6) . . ?
C5 C6 C7 121.3(6) . . ?
C8 C7 C6 118.7(6) . . ?
C8 C7 C12 119.6(6) . . ?
C12 C7 C6 121.8(6) . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.7(6) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.0(6) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 I1 118.6(5) . . ?
C9 C10 C11 121.6(6) . . ?
C11 C10 I1 119.8(5) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 C10 118.6(6) . . ?
C12 C11 H11 120.7 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.4(6) . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C3 119.8(6) . . ?
C18 C13 C3 122.2(6) . . ?
C18 C13 C14 117.9(6) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.3(6) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 119.0(6) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 I2 118.7(5) . . ?
C15 C16 C17 121.1(6) . . ?
C17 C16 I2 120.2(5) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.5(6) . . ?
C18 C17 H17 120.2 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 121.0(6) . . ?
C17 C18 H18 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C10 C11 C12 176.8(6) . . . . ?
I2 C16 C17 C18 178.8(6) . . . . ?
S1 N1 C1 C2 0.5(8) . . . . ?
S1 N1 C1 C6 177.9(6) . . . . ?
S1 N2 C2 C1 0.6(8) . . . . ?
S1 N2 C2 C3 -176.8(6) . . . . ?
N1 S1 N2 C2 -0.3(6) . . . . ?
N1 C1 C2 N2 -0.8(9) . . . . ?
N1 C1 C2 C3 176.8(7) . . . . ?
N1 C1 C6 C5 -176.2(7) . . . . ?
N1 C1 C6 C7 2.7(11) . . . . ?
N2 S1 N1 C1 -0.2(6) . . . . ?
N2 C2 C3 C4 176.3(7) . . . . ?
N2 C2 C3 C13 -1.5(12) . . . . ?
C1 C2 C3 C4 -0.9(11) . . . . ?
C1 C2 C3 C13 -178.7(7) . . . . ?
C1 C6 C7 C8 -135.4(7) . . . . ?
C1 C6 C7 C12 45.9(11) . . . . ?
C2 C1 C6 C5 1.0(10) . . . . ?
C2 C1 C6 C7 179.9(7) . . . . ?
C2 C3 C4 C5 2.5(12) . . . . ?
C2 C3 C13 C14 139.8(8) . . . . ?
C2 C3 C13 C18 -41.6(11) . . . . ?
C3 C4 C5 C6 -2.3(13) . . . . ?
C3 C13 C14 C15 175.6(7) . . . . ?
C3 C13 C18 C17 -175.3(7) . . . . ?
C4 C3 C13 C14 -37.9(11) . . . . ?
C4 C3 C13 C18 140.7(8) . . . . ?
C4 C5 C6 C1 0.5(11) . . . . ?
C4 C5 C6 C7 -178.5(7) . . . . ?
C5 C6 C7 C8 43.5(11) . . . . ?
C5 C6 C7 C12 -135.2(8) . . . . ?
C6 C1 C2 N2 -178.3(6) . . . . ?
C6 C1 C2 C3 -0.8(11) . . . . ?
C6 C7 C8 C9 -178.2(7) . . . . ?
C6 C7 C12 C11 176.1(7) . . . . ?
C7 C8 C9 C10 0.4(12) . . . . ?
C8 C7 C12 C11 -2.6(11) . . . . ?
C8 C9 C10 I1 -178.9(5) . . . . ?
C8 C9 C10 C11 0.9(11) . . . . ?
C9 C10 C11 C12 -2.9(11) . . . . ?
C10 C11 C12 C7 3.8(11) . . . . ?
C12 C7 C8 C9 0.5(11) . . . . ?
C13 C3 C4 C5 -179.6(7) . . . . ?
C13 C14 C15 C16 1.5(12) . . . . ?
C14 C13 C18 C17 3.3(11) . . . . ?
C14 C15 C16 I2 -178.6(6) . . . . ?
C14 C15 C16 C17 0.0(12) . . . . ?
C15 C16 C17 C18 0.3(11) . . . . ?
C16 C17 C18 C13 -2.0(11) . . . . ?
C18 C13 C14 C15 -3.1(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
####################################################################### 
# 
# 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_398_a
_database_code_depnum_ccdc_archive 'CCDC 2179276'
loop_
_audit_author_name
_audit_author_address
'Georgina Rosair'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_audit_creation_date             2020-09-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H16 N2 S'
_chemical_formula_sum            'C26 H16 N2 S'
_chemical_formula_weight         388.47
_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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.0206(3)
_cell_length_b                   29.3812(6)
_cell_length_c                   3.98040(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1756.64(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9251
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      74.381
_cell_measurement_theta_min      5.891
_shelx_estimated_absorpt_T_max   0.903
_shelx_estimated_absorpt_T_min   0.572
_exptl_absorpt_coefficient_mu    1.745
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1298 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.7847.
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    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            16310
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.372
_diffrn_reflns_theta_min         3.008
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8Venture'
_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                1668
_reflns_number_total             1812
_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 V8.40A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1812
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.075
_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)+(0.0528P)²+1.1055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1026
_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), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
;
_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 0.91492(3) 0.750000 0.24051(13) 0.01963(17) Uani 1 2 d S T P . .
N1 N 0.85332(8) 0.70742(4) 0.3508(3) 0.0188(3) Uani 1 1 d . . . . .
C1 C 0.77870(9) 0.72547(4) 0.4837(4) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.70442(9) 0.69995(5) 0.6104(4) 0.0167(3) Uani 1 1 d . . . . .
C3 C 0.63477(9) 0.72580(5) 0.7279(4) 0.0183(3) Uani 1 1 d . . . . .
H3 H 0.583900 0.710503 0.813729 0.022 Uiso 1 1 calc R U . . .
C4 C 0.70682(9) 0.64930(5) 0.6199(4) 0.0166(3) Uani 1 1 d . . . . .
C5 C 0.78008(9) 0.62830(5) 0.7596(4) 0.0180(3) Uani 1 1 d . . . . .
H5 H 0.827146 0.646508 0.845361 0.022 Uiso 1 1 calc R U . . .
C6 C 0.78696(9) 0.58058(5) 0.7786(4) 0.0189(3) Uani 1 1 d . . . . .
H6 H 0.838003 0.567009 0.877726 0.023 Uiso 1 1 calc R U . . .
C7 C 0.72014(9) 0.55373(5) 0.6544(4) 0.0194(3) Uani 1 1 d . . . . .
H7 H 0.725077 0.521547 0.667625 0.023 Uiso 1 1 calc R U . . .
C8 C 0.64361(9) 0.57360(5) 0.5060(4) 0.0170(3) Uani 1 1 d . . . . .
C9 C 0.57500(10) 0.54575(5) 0.3718(4) 0.0204(3) Uani 1 1 d . . . . .
H9 H 0.580684 0.513572 0.381720 0.025 Uiso 1 1 calc R U . . .
C10 C 0.50106(10) 0.56451(5) 0.2289(4) 0.0208(3) Uani 1 1 d . . . . .
H10 H 0.455754 0.545454 0.139717 0.025 Uiso 1 1 calc R U . . .
C11 C 0.49199(9) 0.61236(5) 0.2136(4) 0.0197(3) Uani 1 1 d . . . . .
H11 H 0.440178 0.625360 0.115952 0.024 Uiso 1 1 calc R U . . .
C12 C 0.55741(9) 0.64013(5) 0.3387(4) 0.0182(3) Uani 1 1 d . . . . .
H12 H 0.550441 0.672209 0.324396 0.022 Uiso 1 1 calc R U . . .
C13 C 0.63562(8) 0.62187(5) 0.4895(3) 0.0161(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N1 1.6168(12) . ?
S1 N1 1.6168(12) 7_575 ?
N1 C1 1.3481(18) . ?
C1 C1 1.442(3) 7_575 ?
C1 C2 1.4354(19) . ?
C2 C3 1.3749(19) . ?
C2 C4 1.4892(19) . ?
C3 C3 1.422(3) 7_575 ?
C3 H3 0.9500 . ?
C4 C5 1.3788(19) . ?
C4 C13 1.4360(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.408(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.369(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.418(2) . ?
C8 C9 1.420(2) . ?
C8 C13 1.4248(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.364(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.414(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.371(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.4243(19) . ?

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 N1 101.38(9) . 7_575 ?
C1 N1 S1 106.15(10) . . ?
N1 C1 C1 113.16(8) . 7_575 ?
N1 C1 C2 125.35(13) . . ?
C2 C1 C1 121.48(8) . 7_575 ?
C1 C2 C4 120.80(12) . . ?
C3 C2 C1 114.99(13) . . ?
C3 C2 C4 124.17(13) . . ?
C2 C3 C3 123.53(8) . 7_575 ?
C2 C3 H3 118.2 . . ?
C3 C3 H3 118.2 7_575 . ?
C5 C4 C2 118.48(13) . . ?
C5 C4 C13 119.27(13) . . ?
C13 C4 C2 122.25(12) . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.73(13) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.04(13) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.49(13) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 120.50(13) . . ?
C7 C8 C13 119.82(13) . . ?
C9 C8 C13 119.68(13) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.98(13) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.89(14) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.47(14) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.35(13) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C4 118.64(12) . . ?
C12 C13 C4 123.72(13) . . ?
C12 C13 C8 117.63(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 C1 -0.08(10) . . . 7_575 ?
S1 N1 C1 C2 178.92(12) . . . . ?
N1 S1 N1 C1 0.12(14) 7_575 . . . ?
N1 C1 C2 C3 -178.72(14) . . . . ?
N1 C1 C2 C4 3.3(2) . . . . ?
C1 C1 C2 C3 0.20(16) 7_575 . . . ?
C1 C1 C2 C4 -177.79(9) 7_575 . . . ?
C1 C2 C3 C3 -0.21(16) . . . 7_575 ?
C1 C2 C4 C5 49.62(19) . . . . ?
C1 C2 C4 C13 -130.49(15) . . . . ?
C2 C4 C5 C6 179.78(13) . . . . ?
C2 C4 C13 C8 179.47(13) . . . . ?
C2 C4 C13 C12 0.5(2) . . . . ?
C3 C2 C4 C5 -128.17(15) . . . . ?
C3 C2 C4 C13 51.7(2) . . . . ?
C4 C2 C3 C3 177.70(9) . . . 7_575 ?
C4 C5 C6 C7 0.5(2) . . . . ?
C5 C4 C13 C8 -0.6(2) . . . . ?
C5 C4 C13 C12 -179.63(13) . . . . ?
C5 C6 C7 C8 0.0(2) . . . . ?
C6 C7 C8 C9 178.89(14) . . . . ?
C6 C7 C8 C13 -0.7(2) . . . . ?
C7 C8 C9 C10 179.93(14) . . . . ?
C7 C8 C13 C4 1.1(2) . . . . ?
C7 C8 C13 C12 -179.89(13) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C8 C13 C4 -178.57(13) . . . . ?
C9 C8 C13 C12 0.5(2) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C11 C12 C13 C4 179.02(14) . . . . ?
C11 C12 C13 C8 0.0(2) . . . . ?
C13 C4 C5 C6 -0.1(2) . . . . ?
C13 C8 C9 C10 -0.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
####################################################################### 
# 
# 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_8v00386_0m
_database_code_depnum_ccdc_archive 'CCDC 2179275'
loop_
_audit_author_name
_audit_author_address
'Georgina Rosair'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_audit_creation_date             2022-06-14
_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 H10 F2 N2 S'
_chemical_formula_sum            'C18 H10 F2 N2 S'
_chemical_formula_weight         324.34
_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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3311(7)
_cell_length_b                   9.4843(10)
_cell_length_c                   16.4631(12)
_cell_angle_alpha                90.981(6)
_cell_angle_beta                 94.978(3)
_cell_angle_gamma                106.929(5)
_cell_volume                     1387.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9805
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      74.447
_cell_measurement_theta_min      2.697
_shelx_estimated_absorpt_T_max   0.771
_shelx_estimated_absorpt_T_min   0.371
_exptl_absorpt_coefficient_mu    2.289
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0687 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.7315.
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    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_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       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            44075
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.619
_diffrn_reflns_theta_min         2.697
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                41123
_reflns_number_total             44075
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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         0.700
_refine_diff_density_min         -0.824
_refine_diff_density_rms         0.228
_refine_ls_extinction_coef       0.0125(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         44075
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.189
_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)+(0.0644P)²+2.8225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1698
_refine_ls_wR_factor_ref         0.1731
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.792(3)
 0.208(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18), C21(H21), C22(H22), C26(H26), C27(H27), C29(H29), C30(H30),
  C32(H32), C33(H33), C35(H35), C36(H36)
;
_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 -0.02095(9) 0.80696(9) 0.46500(5) 0.0172(2) Uani 1 1 d . . . . .
F1 F 0.8413(2) 0.9774(2) 0.65089(13) 0.0245(5) Uani 1 1 d . . . . .
F2 F -0.7016(2) 0.2025(2) 0.64638(13) 0.0220(5) Uani 1 1 d . . . . .
N1 N 0.1393(3) 0.8170(3) 0.51372(17) 0.0170(6) Uani 1 1 d . . . . .
N2 N -0.1312(3) 0.6720(3) 0.50856(17) 0.0158(6) Uani 1 1 d . . . . .
C1 C 0.1133(4) 0.7089(4) 0.56766(19) 0.0136(7) Uani 1 1 d . . . . .
C2 C 0.2242(4) 0.6760(4) 0.62381(19) 0.0132(7) Uani 1 1 d . . . . .
C3 C 0.1713(4) 0.5619(4) 0.6735(2) 0.0156(7) Uani 1 1 d . . . . .
H3 H 0.241587 0.535262 0.710818 0.019 Uiso 1 1 calc R U . . .
C4 C 0.0172(4) 0.4815(4) 0.6722(2) 0.0146(7) Uani 1 1 d . . . . .
H4 H -0.010329 0.403767 0.708657 0.018 Uiso 1 1 calc R U . . .
C5 C -0.0954(3) 0.5098(4) 0.62080(19) 0.0121(6) Uani 1 1 d . . . . .
C6 C -0.0439(4) 0.6263(4) 0.56590(19) 0.0136(7) Uani 1 1 d . . . . .
C7 C 0.3859(4) 0.7620(4) 0.6299(2) 0.0147(7) Uani 1 1 d . . . . .
C8 C 0.4595(4) 0.8104(4) 0.5608(2) 0.0144(7) Uani 1 1 d . . . . .
H8 H 0.403854 0.793647 0.508622 0.017 Uiso 1 1 calc R U . . .
C9 C 0.6127(4) 0.8828(4) 0.5671(2) 0.0167(7) Uani 1 1 d . . . . .
H9 H 0.663217 0.914455 0.520048 0.020 Uiso 1 1 calc R U . . .
C10 C 0.6894(4) 0.9071(4) 0.6440(2) 0.0159(7) Uani 1 1 d . . . . .
C11 C 0.6214(4) 0.8658(4) 0.7142(2) 0.0185(7) Uani 1 1 d . . . . .
H11 H 0.677344 0.886862 0.766204 0.022 Uiso 1 1 calc R U . . .
C12 C 0.4684(4) 0.7924(4) 0.7066(2) 0.0157(7) Uani 1 1 d . . . . .
H12 H 0.418885 0.762281 0.754192 0.019 Uiso 1 1 calc R U . . .
C13 C -0.2561(4) 0.4281(4) 0.62412(19) 0.0123(6) Uani 1 1 d . . . . .
C14 C -0.2967(4) 0.2868(4) 0.65526(19) 0.0151(7) Uani 1 1 d . . . . .
H14 H -0.220279 0.242464 0.671586 0.018 Uiso 1 1 calc R U . . .
C15 C -0.4462(4) 0.2098(4) 0.6628(2) 0.0164(7) Uani 1 1 d . . . . .
H15 H -0.472541 0.114225 0.684229 0.020 Uiso 1 1 calc R U . . .
C16 C -0.5552(4) 0.2765(4) 0.6383(2) 0.0153(7) Uani 1 1 d . . . . .
C17 C -0.5215(4) 0.4152(4) 0.6072(2) 0.0157(7) Uani 1 1 d . . . . .
H17 H -0.598849 0.458247 0.590693 0.019 Uiso 1 1 calc R U . . .
C18 C -0.3715(4) 0.4901(4) 0.60067(19) 0.0151(7) Uani 1 1 d . . . . .
H18 H -0.346465 0.586092 0.579729 0.018 Uiso 1 1 calc R U . . .
S2 S 0.48897(9) 0.81368(9) 1.03168(5) 0.0168(2) Uani 1 1 d . . . . .
F3 F 1.2935(2) 0.9443(2) 0.85666(13) 0.0245(5) Uani 1 1 d . . . . .
F4 F -0.2522(2) 0.1684(2) 0.85352(12) 0.0217(5) Uani 1 1 d . . . . .
N3 N 0.6332(3) 0.8129(3) 0.98450(17) 0.0162(6) Uani 1 1 d . . . . .
N4 N 0.3635(3) 0.6716(3) 0.98838(17) 0.0158(6) Uani 1 1 d . . . . .
C19 C 0.5895(4) 0.6959(4) 0.93112(19) 0.0138(7) Uani 1 1 d . . . . .
C20 C 0.6820(4) 0.6510(4) 0.87693(19) 0.0132(7) Uani 1 1 d . . . . .
C21 C 0.6114(4) 0.5284(4) 0.8282(2) 0.0150(7) Uani 1 1 d . . . . .
H21 H 0.668966 0.494037 0.791856 0.018 Uiso 1 1 calc R U . . .
C22 C 0.4572(4) 0.4494(4) 0.8286(2) 0.0146(7) Uani 1 1 d . . . . .
H22 H 0.417091 0.365439 0.792334 0.018 Uiso 1 1 calc R U . . .
C23 C 0.3616(4) 0.4875(4) 0.87871(19) 0.0126(6) Uani 1 1 d . . . . .
C24 C 0.4319(4) 0.6144(4) 0.93250(19) 0.0127(7) Uani 1 1 d . . . . .
C25 C 0.8438(4) 0.7336(4) 0.8728(2) 0.0133(7) Uani 1 1 d . . . . .
C26 C 0.9379(4) 0.8010(4) 0.9419(2) 0.0149(7) Uani 1 1 d . . . . .
H26 H 0.897580 0.798760 0.993114 0.018 Uiso 1 1 calc R U . . .
C27 C 1.0892(4) 0.8711(4) 0.9369(2) 0.0167(7) Uani 1 1 d . . . . .
H27 H 1.153342 0.915398 0.984177 0.020 Uiso 1 1 calc R U . . .
C28 C 1.1445(4) 0.8751(4) 0.8621(2) 0.0174(7) Uani 1 1 d . . . . .
C29 C 1.0559(4) 0.8131(4) 0.7920(2) 0.0177(7) Uani 1 1 d . . . . .
H29 H 1.097097 0.818686 0.740924 0.021 Uiso 1 1 calc R U . . .
C30 C 0.9046(4) 0.7421(4) 0.7978(2) 0.0177(7) Uani 1 1 d . . . . .
H30 H 0.841404 0.698557 0.750052 0.021 Uiso 1 1 calc R U . . .
C31 C 0.2005(4) 0.4038(4) 0.87445(19) 0.0135(7) Uani 1 1 d . . . . .
C32 C 0.1496(4) 0.2574(4) 0.84323(19) 0.0140(7) Uani 1 1 d . . . . .
H32 H 0.220937 0.211362 0.826913 0.017 Uiso 1 1 calc R U . . .
C33 C -0.0023(4) 0.1776(4) 0.8354(2) 0.0167(7) Uani 1 1 d . . . . .
H33 H -0.035210 0.078634 0.813848 0.020 Uiso 1 1 calc R U . . .
C34 C -0.1035(3) 0.2468(4) 0.8600(2) 0.0146(7) Uani 1 1 d . . . . .
C35 C -0.0611(4) 0.3895(4) 0.8915(2) 0.0151(7) Uani 1 1 d . . . . .
H35 H -0.133644 0.433517 0.908270 0.018 Uiso 1 1 calc R U . . .
C36 C 0.0910(4) 0.4680(4) 0.89800(19) 0.0142(7) Uani 1 1 d . . . . .
H36 H 0.121851 0.567303 0.918870 0.017 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 1.611(3) . ?
S1 N2 1.613(3) . ?
F1 C10 1.373(4) . ?
F2 C16 1.361(4) . ?
N1 C1 1.349(4) . ?
N2 C6 1.352(4) . ?
C1 C2 1.434(5) . ?
C1 C6 1.445(5) . ?
C2 C3 1.369(5) . ?
C2 C7 1.485(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.416(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(5) . ?
C5 C6 1.438(5) . ?
C5 C13 1.481(4) . ?
C7 C8 1.395(5) . ?
C7 C12 1.400(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(5) . ?
C10 C11 1.374(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.401(5) . ?
C13 C18 1.400(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(5) . ?
C16 C17 1.379(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(5) . ?
C18 H18 0.9500 . ?
S2 N3 1.613(3) . ?
S2 N4 1.612(3) . ?
F3 C28 1.365(4) . ?
F4 C34 1.365(4) . ?
N3 C19 1.345(5) . ?
N4 C24 1.354(4) . ?
C19 C20 1.434(5) . ?
C19 C24 1.451(5) . ?
C20 C21 1.364(5) . ?
C20 C25 1.493(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.416(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.382(5) . ?
C23 C24 1.437(5) . ?
C23 C31 1.477(5) . ?
C25 C26 1.396(5) . ?
C25 C30 1.397(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.385(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.373(5) . ?
C28 C29 1.374(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.389(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.402(5) . ?
C31 C36 1.410(5) . ?
C32 H32 0.9500 . ?
C32 C33 1.393(5) . ?
C33 H33 0.9500 . ?
C33 C34 1.380(5) . ?
C34 C35 1.373(5) . ?
C35 H35 0.9500 . ?
C35 C36 1.391(5) . ?
C36 H36 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 101.17(15) . . ?
C1 N1 S1 106.6(2) . . ?
C6 N2 S1 106.7(2) . . ?
N1 C1 C2 126.0(3) . . ?
N1 C1 C6 113.0(3) . . ?
C2 C1 C6 120.9(3) . . ?
C1 C2 C7 122.6(3) . . ?
C3 C2 C1 115.8(3) . . ?
C3 C2 C7 121.6(3) . . ?
C2 C3 H3 118.3 . . ?
C2 C3 C4 123.3(3) . . ?
C4 C3 H3 118.3 . . ?
C3 C4 H4 118.1 . . ?
C5 C4 C3 123.7(3) . . ?
C5 C4 H4 118.1 . . ?
C4 C5 C6 114.7(3) . . ?
C4 C5 C13 122.0(3) . . ?
C6 C5 C13 123.3(3) . . ?
N2 C6 C1 112.5(3) . . ?
N2 C6 C5 125.9(3) . . ?
C5 C6 C1 121.6(3) . . ?
C8 C7 C2 121.7(3) . . ?
C8 C7 C12 118.8(3) . . ?
C12 C7 C2 119.5(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 121.1 . . ?
C10 C9 C8 117.9(3) . . ?
C10 C9 H9 121.1 . . ?
F1 C10 C9 118.4(3) . . ?
F1 C10 C11 118.2(3) . . ?
C11 C10 C9 123.4(3) . . ?
C10 C11 H11 121.0 . . ?
C10 C11 C12 117.9(3) . . ?
C12 C11 H11 121.0 . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C5 120.1(3) . . ?
C18 C13 C5 122.1(3) . . ?
C18 C13 C14 117.7(3) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.6(3) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 H15 121.0 . . ?
C16 C15 C14 118.0(3) . . ?
C16 C15 H15 121.0 . . ?
F2 C16 C15 118.4(3) . . ?
F2 C16 C17 118.9(3) . . ?
C17 C16 C15 122.7(3) . . ?
C16 C17 H17 120.9 . . ?
C16 C17 C18 118.1(3) . . ?
C18 C17 H17 120.9 . . ?
C13 C18 H18 119.1 . . ?
C17 C18 C13 121.7(3) . . ?
C17 C18 H18 119.1 . . ?
N4 S2 N3 101.09(15) . . ?
C19 N3 S2 107.1(2) . . ?
C24 N4 S2 106.6(2) . . ?
N3 C19 C20 126.4(3) . . ?
N3 C19 C24 112.5(3) . . ?
C20 C19 C24 121.1(3) . . ?
C19 C20 C25 122.6(3) . . ?
C21 C20 C19 115.4(3) . . ?
C21 C20 C25 122.0(3) . . ?
C20 C21 H21 118.2 . . ?
C20 C21 C22 123.7(3) . . ?
C22 C21 H21 118.2 . . ?
C21 C22 H22 118.1 . . ?
C23 C22 C21 123.8(3) . . ?
C23 C22 H22 118.1 . . ?
C22 C23 C24 114.5(3) . . ?
C22 C23 C31 121.4(3) . . ?
C24 C23 C31 124.1(3) . . ?
N4 C24 C19 112.7(3) . . ?
N4 C24 C23 125.8(3) . . ?
C23 C24 C19 121.5(3) . . ?
C26 C25 C20 122.2(3) . . ?
C26 C25 C30 118.6(3) . . ?
C30 C25 C20 119.3(3) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.9(3) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 120.7 . . ?
C28 C27 C26 118.6(3) . . ?
C28 C27 H27 120.7 . . ?
F3 C28 C27 118.8(3) . . ?
F3 C28 C29 118.4(3) . . ?
C27 C28 C29 122.8(3) . . ?
C28 C29 H29 120.9 . . ?
C28 C29 C30 118.2(3) . . ?
C30 C29 H29 120.9 . . ?
C25 C30 H30 119.5 . . ?
C29 C30 C25 121.0(3) . . ?
C29 C30 H30 119.5 . . ?
C32 C31 C23 120.6(3) . . ?
C32 C31 C36 117.2(3) . . ?
C36 C31 C23 122.1(3) . . ?
C31 C32 H32 119.0 . . ?
C33 C32 C31 122.0(3) . . ?
C33 C32 H32 119.0 . . ?
C32 C33 H33 121.1 . . ?
C34 C33 C32 117.8(3) . . ?
C34 C33 H33 121.1 . . ?
F4 C34 C33 118.1(3) . . ?
F4 C34 C35 118.8(3) . . ?
C35 C34 C33 123.1(3) . . ?
C34 C35 H35 120.9 . . ?
C34 C35 C36 118.2(3) . . ?
C36 C35 H35 120.9 . . ?
C31 C36 H36 119.2 . . ?
C35 C36 C31 121.7(3) . . ?
C35 C36 H36 119.2 . . ?

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 179.6(3) . . . . ?
S1 N1 C1 C6 -1.8(3) . . . . ?
S1 N2 C6 C1 -1.1(3) . . . . ?
S1 N2 C6 C5 178.7(3) . . . . ?
F1 C10 C11 C12 -178.8(3) . . . . ?
F2 C16 C17 C18 179.0(3) . . . . ?
N1 S1 N2 C6 0.0(3) . . . . ?
N1 C1 C2 C3 179.3(3) . . . . ?
N1 C1 C2 C7 1.0(5) . . . . ?
N1 C1 C6 N2 2.0(4) . . . . ?
N1 C1 C6 C5 -177.8(3) . . . . ?
N2 S1 N1 C1 1.1(3) . . . . ?
C1 C2 C3 C4 -1.3(5) . . . . ?
C1 C2 C7 C8 -40.2(5) . . . . ?
C1 C2 C7 C12 141.5(3) . . . . ?
C2 C1 C6 N2 -179.4(3) . . . . ?
C2 C1 C6 C5 0.9(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C2 C7 C8 C9 -176.0(3) . . . . ?
C2 C7 C12 C11 176.6(3) . . . . ?
C3 C2 C7 C8 141.5(3) . . . . ?
C3 C2 C7 C12 -36.7(5) . . . . ?
C3 C4 C5 C6 1.7(5) . . . . ?
C3 C4 C5 C13 -176.9(3) . . . . ?
C4 C5 C6 N2 178.2(3) . . . . ?
C4 C5 C6 C1 -2.1(5) . . . . ?
C4 C5 C13 C14 -24.3(5) . . . . ?
C4 C5 C13 C18 152.4(3) . . . . ?
C5 C13 C14 C15 176.9(3) . . . . ?
C5 C13 C18 C17 -177.2(3) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
C6 C1 C2 C7 -177.5(3) . . . . ?
C6 C5 C13 C14 157.1(3) . . . . ?
C6 C5 C13 C18 -26.1(5) . . . . ?
C7 C2 C3 C4 177.1(3) . . . . ?
C7 C8 C9 C10 -1.0(5) . . . . ?
C8 C7 C12 C11 -1.7(5) . . . . ?
C8 C9 C10 F1 179.4(3) . . . . ?
C8 C9 C10 C11 -1.1(5) . . . . ?
C9 C10 C11 C12 1.7(5) . . . . ?
C10 C11 C12 C7 -0.3(5) . . . . ?
C12 C7 C8 C9 2.3(5) . . . . ?
C13 C5 C6 N2 -3.2(5) . . . . ?
C13 C5 C6 C1 176.5(3) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C13 C18 C17 -0.4(5) . . . . ?
C14 C15 C16 F2 -179.3(3) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C15 C16 C17 C18 -0.2(5) . . . . ?
C16 C17 C18 C13 0.5(5) . . . . ?
C18 C13 C14 C15 0.0(5) . . . . ?
S2 N3 C19 C20 -179.0(3) . . . . ?
S2 N3 C19 C24 1.3(3) . . . . ?
S2 N4 C24 C19 0.7(3) . . . . ?
S2 N4 C24 C23 -179.1(3) . . . . ?
F3 C28 C29 C30 179.7(3) . . . . ?
F4 C34 C35 C36 179.8(3) . . . . ?
N3 S2 N4 C24 0.1(2) . . . . ?
N3 C19 C20 C21 -179.7(3) . . . . ?
N3 C19 C20 C25 -0.7(5) . . . . ?
N3 C19 C24 N4 -1.3(4) . . . . ?
N3 C19 C24 C23 178.5(3) . . . . ?
N4 S2 N3 C19 -0.8(3) . . . . ?
C19 C20 C21 C22 0.9(5) . . . . ?
C19 C20 C25 C26 36.0(5) . . . . ?
C19 C20 C25 C30 -145.1(3) . . . . ?
C20 C19 C24 N4 179.0(3) . . . . ?
C20 C19 C24 C23 -1.2(5) . . . . ?
C20 C21 C22 C23 -0.3(5) . . . . ?
C20 C25 C26 C27 177.0(3) . . . . ?
C20 C25 C30 C29 -177.5(3) . . . . ?
C21 C20 C25 C26 -145.0(3) . . . . ?
C21 C20 C25 C30 33.8(5) . . . . ?
C21 C22 C23 C24 -1.0(5) . . . . ?
C21 C22 C23 C31 177.9(3) . . . . ?
C22 C23 C24 N4 -178.5(3) . . . . ?
C22 C23 C24 C19 1.7(4) . . . . ?
C22 C23 C31 C32 23.1(5) . . . . ?
C22 C23 C31 C36 -154.2(3) . . . . ?
C23 C31 C32 C33 -177.4(3) . . . . ?
C23 C31 C36 C35 178.0(3) . . . . ?
C24 C19 C20 C21 -0.1(4) . . . . ?
C24 C19 C20 C25 178.9(3) . . . . ?
C24 C23 C31 C32 -158.1(3) . . . . ?
C24 C23 C31 C36 24.5(5) . . . . ?
C25 C20 C21 C22 -178.2(3) . . . . ?
C25 C26 C27 C28 1.1(5) . . . . ?
C26 C25 C30 C29 1.3(5) . . . . ?
C26 C27 C28 F3 179.8(3) . . . . ?
C26 C27 C28 C29 0.3(5) . . . . ?
C27 C28 C29 C30 -0.8(5) . . . . ?
C28 C29 C30 C25 0.0(5) . . . . ?
C30 C25 C26 C27 -1.9(5) . . . . ?
C31 C23 C24 N4 2.6(5) . . . . ?
C31 C23 C24 C19 -177.1(3) . . . . ?
C31 C32 C33 C34 -0.4(5) . . . . ?
C32 C31 C36 C35 0.6(5) . . . . ?
C32 C33 C34 F4 -179.2(3) . . . . ?
C32 C33 C34 C35 0.1(5) . . . . ?
C33 C34 C35 C36 0.6(5) . . . . ?
C34 C35 C36 C31 -0.9(5) . . . . ?
C36 C31 C32 C33 0.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.792(3)
2 0.208(3)

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
####################################################################### 
# 
# 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_mo_8v00410_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2179278'
loop_
_audit_author_name
_audit_author_address
'Georgina Rosair'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT431_mo_8v00410_0m_a     
;
PROBLEM: Short Inter HL..A Contact  Cl1      ..S1       .       3.36 Ang.
RESPONSE: Short Inter HL..A Contact Cl1 ..S1; no space group ambiguity 
;
# Added during the CSD deposition process: Wednesday 15 June 2022 11:51 AM
# end Validation Reply Form

_audit_creation_date             2022-06-09
_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 H10 Cl2 N2 S'
_chemical_formula_sum            'C18 H10 Cl2 N2 S'
_chemical_formula_weight         357.24
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4442(4)
_cell_length_b                   9.5031(4)
_cell_length_c                   17.4731(6)
_cell_angle_alpha                90.2759(19)
_cell_angle_beta                 94.3850(18)
_cell_angle_gamma                108.3803(18)
_cell_volume                     1483.14(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7373
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.395
_cell_measurement_theta_min      2.476
_shelx_estimated_absorpt_T_max   0.913
_shelx_estimated_absorpt_T_min   0.777
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0689 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.9011.
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    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35257
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.486
_diffrn_reflns_theta_min         2.339
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5960
_reflns_number_total             8999
_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 V8.40A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 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         0.627
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         8999
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.052
_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)+(0.0347P)²+2.7833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1300
_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:
 C4'(H4'), C5'(H5'), C8'(H8'), C9'(H9'), C11'(H11'), C12'(H12'), C14'(H14'),
 C15'(H15'), C17'(H17'), C18'(H18'), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11),
 C12(H12), C14(H14), C15(H15), 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 0.88700(8) 0.95606(8) 0.64482(4) 0.01962(16) Uani 1 1 d . . . . .
Cl2' Cl -0.74324(8) 0.13587(9) 0.65272(5) 0.02286(17) Uani 1 1 d . . . . .
S1' S -0.01428(8) 0.78037(9) 0.48146(4) 0.01860(16) Uani 1 1 d . . . . .
N1' N 0.1444(3) 0.7881(3) 0.52545(13) 0.0155(5) Uani 1 1 d . . . . .
N2' N -0.1269(3) 0.6445(3) 0.52348(14) 0.0163(5) Uani 1 1 d . . . . .
C1' C 0.1161(3) 0.6795(3) 0.57677(15) 0.0134(5) Uani 1 1 d . . . . .
C2' C -0.0414(3) 0.5978(3) 0.57692(16) 0.0131(5) Uani 1 1 d . . . . .
C3' C -0.0948(3) 0.4808(3) 0.62851(16) 0.0129(5) Uani 1 1 d . . . . .
C4' C 0.0134(3) 0.4509(3) 0.67691(16) 0.0152(5) Uani 1 1 d . . . . .
H4' H -0.017134 0.373945 0.712444 0.018 Uiso 1 1 calc R U . . .
C5' C 0.1684(3) 0.5296(3) 0.67627(16) 0.0148(5) Uani 1 1 d . . . . .
H5' H 0.236777 0.501577 0.710810 0.018 Uiso 1 1 calc R U . . .
C6' C 0.2248(3) 0.6449(3) 0.62793(15) 0.0120(5) Uani 1 1 d . . . . .
C7' C 0.3863(3) 0.7271(3) 0.63079(16) 0.0139(5) Uani 1 1 d . . . . .
C8' C 0.4583(3) 0.7822(3) 0.56442(16) 0.0156(6) Uani 1 1 d . . . . .
H8' H 0.401090 0.770786 0.516325 0.019 Uiso 1 1 calc R U . . .
C9' C 0.6124(3) 0.8532(3) 0.56836(17) 0.0172(6) Uani 1 1 d . . . . .
H9' H 0.660603 0.889414 0.523359 0.021 Uiso 1 1 calc R U . . .
C10' C 0.6940(3) 0.8699(3) 0.63879(17) 0.0150(5) Uani 1 1 d . . . . .
C11' C 0.6256(3) 0.8207(3) 0.70511(16) 0.0142(5) Uani 1 1 d . . . . .
H11' H 0.683052 0.836850 0.753269 0.017 Uiso 1 1 calc R U . . .
C12' C 0.4735(3) 0.7478(3) 0.70110(16) 0.0146(5) Uani 1 1 d . . . . .
H12' H 0.427208 0.711174 0.746561 0.018 Uiso 1 1 calc R U . . .
C13' C -0.2557(3) 0.3962(3) 0.63157(15) 0.0126(5) Uani 1 1 d . . . . .
C14' C -0.2989(3) 0.2498(3) 0.65700(17) 0.0168(6) Uani 1 1 d . . . . .
H14' H -0.224357 0.204370 0.670073 0.020 Uiso 1 1 calc R U . . .
C15' C -0.4478(3) 0.1704(3) 0.66337(17) 0.0173(6) Uani 1 1 d . . . . .
H15' H -0.475048 0.072050 0.681365 0.021 Uiso 1 1 calc R U . . .
C16' C -0.5564(3) 0.2358(3) 0.64325(16) 0.0146(5) Uani 1 1 d . . . . .
C17' C -0.5192(3) 0.3794(3) 0.61654(17) 0.0168(6) Uani 1 1 d . . . . .
H17' H -0.594948 0.422583 0.602121 0.020 Uiso 1 1 calc R U . . .
C18' C -0.3688(3) 0.4588(3) 0.61128(16) 0.0156(6) Uani 1 1 d . . . . .
H18' H -0.342396 0.557361 0.593578 0.019 Uiso 1 1 calc R U . . .
Cl1 Cl -0.28933(8) 0.11968(9) 0.85824(4) 0.02055(16) Uani 1 1 d . . . . .
Cl2 Cl 1.34261(8) 0.93500(8) 0.84696(4) 0.01920(15) Uani 1 1 d . . . . .
S1 S 0.50153(8) 0.79442(9) 1.01522(4) 0.01749(15) Uani 1 1 d . . . . .
N1 N 0.3727(3) 0.6522(3) 0.97608(14) 0.0156(5) Uani 1 1 d . . . . .
N2 N 0.6452(3) 0.7912(3) 0.97155(14) 0.0156(5) Uani 1 1 d . . . . .
C1 C 0.4390(3) 0.5931(3) 0.92422(15) 0.0133(5) Uani 1 1 d . . . . .
C2 C 0.5967(3) 0.6722(3) 0.92247(16) 0.0131(5) Uani 1 1 d . . . . .
C3 C 0.6864(3) 0.6256(3) 0.87225(15) 0.0135(5) Uani 1 1 d . . . . .
C4 C 0.6138(3) 0.5021(3) 0.82668(16) 0.0151(5) Uani 1 1 d . . . . .
H4 H 0.669976 0.466542 0.792907 0.018 Uiso 1 1 calc R U . . .
C5 C 0.4582(3) 0.4248(3) 0.82779(16) 0.0152(6) Uani 1 1 d . . . . .
H5 H 0.415159 0.340665 0.794259 0.018 Uiso 1 1 calc R U . . .
C6 C 0.3662(3) 0.4662(3) 0.87529(16) 0.0125(5) Uani 1 1 d . . . . .
C7 C 0.2042(3) 0.3819(3) 0.87331(15) 0.0125(5) Uani 1 1 d . . . . .
C8 C 0.0989(3) 0.4483(3) 0.89389(16) 0.0149(5) Uani 1 1 d . . . . .
H8 H 0.131475 0.549425 0.910811 0.018 Uiso 1 1 calc R U . . .
C9 C -0.0530(3) 0.3675(3) 0.88980(17) 0.0163(6) Uani 1 1 d . . . . .
H9 H -0.123761 0.412693 0.904532 0.020 Uiso 1 1 calc R U . . .
C10 C -0.0997(3) 0.2214(3) 0.86415(16) 0.0150(6) Uani 1 1 d . . . . .
C11 C 0.0010(3) 0.1520(3) 0.84448(16) 0.0169(6) Uani 1 1 d . . . . .
H11 H -0.032877 0.050758 0.827775 0.020 Uiso 1 1 calc R U . . .
C12 C 0.1532(3) 0.2323(3) 0.84939(16) 0.0152(6) Uani 1 1 d . . . . .
H12 H 0.223167 0.184803 0.836340 0.018 Uiso 1 1 calc R U . . .
C13 C 0.8488(3) 0.7059(3) 0.86812(16) 0.0133(5) Uani 1 1 d . . . . .
C14 C 0.9103(3) 0.7102(3) 0.79764(16) 0.0150(6) Uani 1 1 d . . . . .
H14 H 0.847404 0.664030 0.753506 0.018 Uiso 1 1 calc R U . . .
C15 C 1.0628(3) 0.7813(3) 0.79075(16) 0.0153(6) Uani 1 1 d . . . . .
H15 H 1.103790 0.783558 0.742607 0.018 Uiso 1 1 calc R U . . .
C16 C 1.1530(3) 0.8485(3) 0.85596(17) 0.0148(5) Uani 1 1 d . . . . .
C17 C 1.0953(3) 0.8469(3) 0.92647(16) 0.0162(6) Uani 1 1 d . . . . .
H17 H 1.158596 0.893580 0.970386 0.019 Uiso 1 1 calc R U . . .
C18 C 0.9429(3) 0.7759(3) 0.93231(16) 0.0152(5) Uani 1 1 d . . . . .
H18 H 0.902515 0.775057 0.980522 0.018 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
Cl1' C10' 1.742(3) . ?
Cl2' C16' 1.741(3) . ?
S1' N1' 1.611(3) . ?
S1' N2' 1.613(2) . ?
N1' C1' 1.346(3) . ?
N2' C2' 1.355(4) . ?
C1' C2' 1.444(4) . ?
C1' C6' 1.427(4) . ?
C2' C3' 1.425(4) . ?
C3' C4' 1.376(4) . ?
C3' C13' 1.484(4) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.420(4) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.381(4) . ?
C6' C7' 1.475(4) . ?
C7' C8' 1.408(4) . ?
C7' C12' 1.402(4) . ?
C8' H8' 0.9500 . ?
C8' C9' 1.394(4) . ?
C9' H9' 0.9500 . ?
C9' C10' 1.381(4) . ?
C10' C11' 1.381(4) . ?
C11' H11' 0.9500 . ?
C11' C12' 1.381(4) . ?
C12' H12' 0.9500 . ?
C13' C14' 1.406(4) . ?
C13' C18' 1.402(4) . ?
C14' H14' 0.9500 . ?
C14' C15' 1.383(4) . ?
C15' H15' 0.9500 . ?
C15' C16' 1.383(4) . ?
C16' C17' 1.390(4) . ?
C17' H17' 0.9500 . ?
C17' C18' 1.392(4) . ?
C18' H18' 0.9500 . ?
Cl1 C10 1.741(3) . ?
Cl2 C16 1.739(3) . ?
S1 N1 1.613(3) . ?
S1 N2 1.615(3) . ?
N1 C1 1.354(4) . ?
N2 C2 1.352(4) . ?
C1 C2 1.444(4) . ?
C1 C6 1.427(4) . ?
C2 C3 1.424(4) . ?
C3 C4 1.372(4) . ?
C3 C13 1.490(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.422(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(4) . ?
C6 C7 1.484(4) . ?
C7 C8 1.401(4) . ?
C7 C12 1.400(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(4) . ?
C10 C11 1.379(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(4) . ?
C13 C18 1.399(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.399(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(4) . ?
C16 C17 1.383(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.395(4) . ?
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
N1' S1' N2' 101.23(13) . . ?
C1' N1' S1' 106.71(19) . . ?
C2' N2' S1' 106.40(19) . . ?
N1' C1' C2' 112.9(2) . . ?
N1' C1' C6' 125.9(3) . . ?
C6' C1' C2' 121.2(2) . . ?
N2' C2' C1' 112.7(2) . . ?
N2' C2' C3' 125.7(3) . . ?
C3' C2' C1' 121.6(3) . . ?
C2' C3' C13' 123.2(3) . . ?
C4' C3' C2' 115.5(2) . . ?
C4' C3' C13' 121.3(3) . . ?
C3' C4' H4' 118.4 . . ?
C3' C4' C5' 123.1(3) . . ?
C5' C4' H4' 118.4 . . ?
C4' C5' H5' 118.4 . . ?
C6' C5' C4' 123.3(3) . . ?
C6' C5' H5' 118.4 . . ?
C1' C6' C7' 123.1(2) . . ?
C5' C6' C1' 115.4(2) . . ?
C5' C6' C7' 121.6(3) . . ?
C8' C7' C6' 122.2(3) . . ?
C12' C7' C6' 119.6(2) . . ?
C12' C7' C8' 118.2(3) . . ?
C7' C8' H8' 119.6 . . ?
C9' C8' C7' 120.9(3) . . ?
C9' C8' H8' 119.6 . . ?
C8' C9' H9' 120.5 . . ?
C10' C9' C8' 118.9(3) . . ?
C10' C9' H9' 120.5 . . ?
C9' C10' Cl1' 119.7(2) . . ?
C11' C10' Cl1' 118.9(2) . . ?
C11' C10' C9' 121.4(3) . . ?
C10' C11' H11' 120.1 . . ?
C12' C11' C10' 119.7(3) . . ?
C12' C11' H11' 120.1 . . ?
C7' C12' H12' 119.6 . . ?
C11' C12' C7' 120.8(3) . . ?
C11' C12' H12' 119.6 . . ?
C14' C13' C3' 120.1(3) . . ?
C18' C13' C3' 122.0(3) . . ?
C18' C13' C14' 117.8(3) . . ?
C13' C14' H14' 119.3 . . ?
C15' C14' C13' 121.4(3) . . ?
C15' C14' H14' 119.3 . . ?
C14' C15' H15' 120.4 . . ?
C16' C15' C14' 119.3(3) . . ?
C16' C15' H15' 120.4 . . ?
C15' C16' Cl2' 118.9(2) . . ?
C15' C16' C17' 121.4(3) . . ?
C17' C16' Cl2' 119.7(2) . . ?
C16' C17' H17' 120.6 . . ?
C16' C17' C18' 118.8(3) . . ?
C18' C17' H17' 120.6 . . ?
C13' C18' H18' 119.3 . . ?
C17' C18' C13' 121.3(3) . . ?
C17' C18' H18' 119.3 . . ?
N1 S1 N2 101.66(13) . . ?
C1 N1 S1 106.18(19) . . ?
C2 N2 S1 106.09(19) . . ?
N1 C1 C2 112.9(3) . . ?
N1 C1 C6 125.6(3) . . ?
C6 C1 C2 121.5(3) . . ?
N2 C2 C1 113.1(3) . . ?
N2 C2 C3 125.6(3) . . ?
C3 C2 C1 121.3(3) . . ?
C2 C3 C13 122.7(3) . . ?
C4 C3 C2 116.0(3) . . ?
C4 C3 C13 121.4(3) . . ?
C3 C4 H4 118.6 . . ?
C3 C4 C5 122.9(3) . . ?
C5 C4 H4 118.6 . . ?
C4 C5 H5 118.3 . . ?
C6 C5 C4 123.3(3) . . ?
C6 C5 H5 118.3 . . ?
C1 C6 C7 124.1(3) . . ?
C5 C6 C1 115.1(2) . . ?
C5 C6 C7 120.9(3) . . ?
C8 C7 C6 121.9(3) . . ?
C12 C7 C6 119.7(3) . . ?
C12 C7 C8 118.4(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 Cl1 119.8(2) . . ?
C11 C10 Cl1 118.7(2) . . ?
C11 C10 C9 121.5(3) . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.9(3) . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C3 118.8(3) . . ?
C14 C13 C18 118.5(3) . . ?
C18 C13 C3 122.6(2) . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.3(3) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.5(3) . . ?
C16 C15 H15 120.8 . . ?
C15 C16 Cl2 118.1(2) . . ?
C17 C16 Cl2 120.3(2) . . ?
C17 C16 C15 121.6(3) . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.2(3) . . ?
C18 C17 H17 120.4 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.9(3) . . ?
C17 C18 H18 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1' C10' C11' C12' -177.9(2) . . . . ?
Cl2' C16' C17' C18' 178.4(2) . . . . ?
S1' N1' C1' C2' -1.5(3) . . . . ?
S1' N1' C1' C6' 179.4(2) . . . . ?
S1' N2' C2' C1' -1.6(3) . . . . ?
S1' N2' C2' C3' 179.0(2) . . . . ?
N1' S1' N2' C2' 0.6(2) . . . . ?
N1' C1' C2' N2' 2.1(4) . . . . ?
N1' C1' C2' C3' -178.4(3) . . . . ?
N1' C1' C6' C5' 179.1(3) . . . . ?
N1' C1' C6' C7' 0.2(5) . . . . ?
N2' S1' N1' C1' 0.5(2) . . . . ?
N2' C2' C3' C4' 178.8(3) . . . . ?
N2' C2' C3' C13' -1.9(5) . . . . ?
C1' C2' C3' C4' -0.6(4) . . . . ?
C1' C2' C3' C13' 178.7(3) . . . . ?
C1' C6' C7' C8' -36.1(4) . . . . ?
C1' C6' C7' C12' 146.0(3) . . . . ?
C2' C1' C6' C5' 0.1(4) . . . . ?
C2' C1' C6' C7' -178.8(3) . . . . ?
C2' C3' C4' C5' -0.2(4) . . . . ?
C2' C3' C13' C14' 153.1(3) . . . . ?
C2' C3' C13' C18' -28.3(4) . . . . ?
C3' C4' C5' C6' 1.1(5) . . . . ?
C3' C13' C14' C15' 177.4(3) . . . . ?
C3' C13' C18' C17' -178.1(3) . . . . ?
C4' C3' C13' C14' -27.5(4) . . . . ?
C4' C3' C13' C18' 151.0(3) . . . . ?
C4' C5' C6' C1' -0.9(4) . . . . ?
C4' C5' C6' C7' 178.0(3) . . . . ?
C5' C6' C7' C8' 145.0(3) . . . . ?
C5' C6' C7' C12' -32.9(4) . . . . ?
C6' C1' C2' N2' -178.7(3) . . . . ?
C6' C1' C2' C3' 0.7(4) . . . . ?
C6' C7' C8' C9' -176.9(3) . . . . ?
C6' C7' C12' C11' 178.2(3) . . . . ?
C7' C8' C9' C10' -0.5(5) . . . . ?
C8' C7' C12' C11' 0.2(4) . . . . ?
C8' C9' C10' Cl1' 179.1(2) . . . . ?
C8' C9' C10' C11' -1.3(5) . . . . ?
C9' C10' C11' C12' 2.6(4) . . . . ?
C10' C11' C12' C7' -2.0(4) . . . . ?
C12' C7' C8' C9' 1.0(4) . . . . ?
C13' C3' C4' C5' -179.6(3) . . . . ?
C13' C14' C15' C16' 0.9(5) . . . . ?
C14' C13' C18' C17' 0.5(4) . . . . ?
C14' C15' C16' Cl2' -179.1(2) . . . . ?
C14' C15' C16' C17' 0.2(4) . . . . ?
C15' C16' C17' C18' -1.0(4) . . . . ?
C16' C17' C18' C13' 0.7(4) . . . . ?
C18' C13' C14' C15' -1.3(4) . . . . ?
Cl1 C10 C11 C12 -179.7(2) . . . . ?
Cl2 C16 C17 C18 -179.5(2) . . . . ?
S1 N1 C1 C2 1.1(3) . . . . ?
S1 N1 C1 C6 -179.1(2) . . . . ?
S1 N2 C2 C1 1.2(3) . . . . ?
S1 N2 C2 C3 -179.6(2) . . . . ?
N1 S1 N2 C2 -0.5(2) . . . . ?
N1 C1 C2 N2 -1.6(3) . . . . ?
N1 C1 C2 C3 179.2(2) . . . . ?
N1 C1 C6 C5 -178.9(3) . . . . ?
N1 C1 C6 C7 1.4(4) . . . . ?
N2 S1 N1 C1 -0.3(2) . . . . ?
N2 C2 C3 C4 -179.4(3) . . . . ?
N2 C2 C3 C13 -0.1(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C3 C13 179.1(3) . . . . ?
C1 C6 C7 C8 26.5(4) . . . . ?
C1 C6 C7 C12 -154.4(3) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
C2 C1 C6 C7 -178.8(3) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C2 C3 C13 C14 -146.4(3) . . . . ?
C2 C3 C13 C18 34.3(4) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C3 C13 C14 C15 -178.6(3) . . . . ?
C3 C13 C18 C17 178.4(3) . . . . ?
C4 C3 C13 C14 32.9(4) . . . . ?
C4 C3 C13 C18 -146.4(3) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C4 C5 C6 C7 179.4(3) . . . . ?
C5 C6 C7 C8 -153.2(3) . . . . ?
C5 C6 C7 C12 26.0(4) . . . . ?
C6 C1 C2 N2 178.6(2) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C6 C7 C8 C9 178.5(3) . . . . ?
C6 C7 C12 C11 -177.8(3) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C8 C7 C12 C11 1.4(4) . . . . ?
C8 C9 C10 Cl1 -179.6(2) . . . . ?
C8 C9 C10 C11 1.8(4) . . . . ?
C9 C10 C11 C12 -1.1(4) . . . . ?
C10 C11 C12 C7 -0.6(4) . . . . ?
C12 C7 C8 C9 -0.7(4) . . . . ?
C13 C3 C4 C5 -178.5(3) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C14 C13 C18 C17 -0.8(4) . . . . ?
C14 C15 C16 Cl2 179.4(2) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C16 C17 C18 C13 0.5(4) . . . . ?
C18 C13 C14 C15 0.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Grown by cooling a saturated solution in hot toluene.'
####################################################################### 
# 
# 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_8v00459_0m
_database_code_depnum_ccdc_archive 'CCDC 2179281'
loop_
_audit_author_name
_audit_author_address
'Georgina Rosair'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_audit_creation_date             2022-06-14
_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         'C20 H10 F6 N2 S'
_chemical_formula_sum            'C20 H10 F6 N2 S'
_chemical_formula_weight         424.36
_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'
F F 0.0727 0.0534 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6001(3)
_cell_length_b                   9.7278(3)
_cell_length_c                   10.4526(3)
_cell_angle_alpha                90.6038(9)
_cell_angle_beta                 117.0952(9)
_cell_angle_gamma                99.9999(9)
_cell_volume                     851.33(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      74.740
_cell_measurement_theta_min      4.640
_shelx_estimated_absorpt_T_max   0.797
_shelx_estimated_absorpt_T_min   0.517
_exptl_absorpt_coefficient_mu    2.375
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0835 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.7985.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15906
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.731
_diffrn_reflns_theta_min         4.640
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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                3332
_reflns_number_total             3444
_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 V8.40A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.056
_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)+(0.0370P)²+0.4376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0794
_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:
 C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C15(H15), C16(H16),
 C18(H18), C19(H19)
;
_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 0.75857(4) 0.54070(3) 0.51796(3) 0.01912(10) Uani 1 1 d . . . . .
F1 F 0.87275(11) 0.32382(9) 1.33126(9) 0.0320(2) Uani 1 1 d . . . . .
F2 F 0.95286(11) 0.13965(11) 1.30137(9) 0.0362(2) Uani 1 1 d . . . . .
F3 F 0.71984(11) 0.12215(11) 1.28492(9) 0.0371(2) Uani 1 1 d . . . . .
F4 F 0.05936(10) 0.36593(9) -0.33955(9) 0.02794(19) Uani 1 1 d . . . . .
F5 F 0.14306(11) 0.18089(10) -0.36079(9) 0.0339(2) Uani 1 1 d . . . . .
F6 F -0.08292(11) 0.16293(10) -0.35882(9) 0.0344(2) Uani 1 1 d . . . . .
N1 N 0.74281(13) 0.44990(11) 0.64008(12) 0.0183(2) Uani 1 1 d . . . . .
N2 N 0.60872(13) 0.45796(11) 0.37329(12) 0.0183(2) Uani 1 1 d . . . . .
C1 C 0.61351(15) 0.34566(13) 0.57038(14) 0.0163(2) Uani 1 1 d . . . . .
C2 C 0.53712(15) 0.34948(13) 0.41617(14) 0.0158(2) Uani 1 1 d . . . . .
C3 C 0.39801(15) 0.24705(13) 0.32326(13) 0.0161(2) Uani 1 1 d . . . . .
C4 C 0.34511(15) 0.14639(13) 0.39137(14) 0.0175(2) Uani 1 1 d . . . . .
H4 H 0.254151 0.075662 0.333680 0.021 Uiso 1 1 calc R U . . .
C5 C 0.41967(15) 0.14303(13) 0.54344(14) 0.0178(2) Uani 1 1 d . . . . .
H5 H 0.375579 0.070933 0.582837 0.021 Uiso 1 1 calc R U . . .
C6 C 0.55318(15) 0.23963(13) 0.63660(13) 0.0160(2) Uani 1 1 d . . . . .
C7 C 0.62751(14) 0.23328(13) 0.79521(13) 0.0161(2) Uani 1 1 d . . . . .
C8 C 0.61914(15) 0.10291(13) 0.85006(14) 0.0176(3) Uani 1 1 d . . . . .
H8 H 0.568716 0.019812 0.785039 0.021 Uiso 1 1 calc R U . . .
C9 C 0.68294(15) 0.09311(13) 0.99700(14) 0.0182(3) Uani 1 1 d . . . . .
H9 H 0.675736 0.003937 1.032294 0.022 Uiso 1 1 calc R U . . .
C10 C 0.75778(15) 0.21421(13) 1.09319(13) 0.0172(2) Uani 1 1 d . . . . .
C11 C 0.76895(16) 0.34466(13) 1.04144(14) 0.0202(3) Uani 1 1 d . . . . .
H11 H 0.820867 0.427225 1.107131 0.024 Uiso 1 1 calc R U . . .
C12 C 0.70412(16) 0.35415(13) 0.89359(14) 0.0199(3) Uani 1 1 d . . . . .
H12 H 0.711787 0.443525 0.858778 0.024 Uiso 1 1 calc R U . . .
C13 C 0.82558(15) 0.20067(14) 1.25192(14) 0.0197(3) Uani 1 1 d . . . . .
C14 C 0.31424(15) 0.24850(12) 0.16414(13) 0.0164(2) Uani 1 1 d . . . . .
C15 C 0.14917(16) 0.20003(14) 0.08797(14) 0.0206(3) Uani 1 1 d . . . . .
H15 H 0.091436 0.170000 0.139546 0.025 Uiso 1 1 calc R U . . .
C16 C 0.06765(16) 0.19482(14) -0.06161(15) 0.0216(3) Uani 1 1 d . . . . .
H16 H -0.044708 0.161784 -0.111697 0.026 Uiso 1 1 calc R U . . .
C17 C 0.15197(16) 0.23840(13) -0.13742(14) 0.0187(3) Uani 1 1 d . . . . .
C18 C 0.31621(16) 0.28871(13) -0.06360(14) 0.0196(3) Uani 1 1 d . . . . .
H18 H 0.373359 0.319305 -0.115548 0.023 Uiso 1 1 calc R U . . .
C19 C 0.39643(15) 0.29416(13) 0.08583(14) 0.0182(3) Uani 1 1 d . . . . .
H19 H 0.508430 0.329253 0.135685 0.022 Uiso 1 1 calc R U . . .
C20 C 0.06770(16) 0.23598(14) -0.29840(15) 0.0218(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N1 1.6079(11) . ?
S1 N2 1.6108(11) . ?
F1 C13 1.3329(16) . ?
F2 C13 1.3400(16) . ?
F3 C13 1.3372(15) . ?
F4 C20 1.3434(16) . ?
F5 C20 1.3390(16) . ?
F6 C20 1.3403(16) . ?
N1 C1 1.3503(16) . ?
N2 C2 1.3512(16) . ?
C1 C2 1.4392(17) . ?
C1 C6 1.4322(17) . ?
C2 C3 1.4337(17) . ?
C3 C4 1.3765(17) . ?
C3 C14 1.4830(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.4187(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3782(18) . ?
C6 C7 1.4838(17) . ?
C7 C8 1.4019(17) . ?
C7 C12 1.4022(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3820(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3921(18) . ?
C10 C11 1.3909(18) . ?
C10 C13 1.4981(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3896(19) . ?
C12 H12 0.9500 . ?
C14 C15 1.3966(18) . ?
C14 C19 1.4016(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3890(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.3911(19) . ?
C17 C18 1.3916(19) . ?
C17 C20 1.4964(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.3870(18) . ?
C19 H19 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 101.46(6) . . ?
C1 N1 S1 106.45(9) . . ?
C2 N2 S1 106.22(9) . . ?
N1 C1 C2 112.84(11) . . ?
N1 C1 C6 125.93(12) . . ?
C6 C1 C2 121.23(11) . . ?
N2 C2 C1 113.03(11) . . ?
N2 C2 C3 125.80(12) . . ?
C3 C2 C1 121.17(11) . . ?
C2 C3 C14 122.89(11) . . ?
C4 C3 C2 115.62(11) . . ?
C4 C3 C14 121.48(11) . . ?
C3 C4 H4 118.4 . . ?
C3 C4 C5 123.26(11) . . ?
C5 C4 H4 118.4 . . ?
C4 C5 H5 118.5 . . ?
C6 C5 C4 122.97(12) . . ?
C6 C5 H5 118.5 . . ?
C1 C6 C7 122.78(11) . . ?
C5 C6 C1 115.73(11) . . ?
C5 C6 C7 121.49(11) . . ?
C8 C7 C6 119.51(11) . . ?
C8 C7 C12 118.24(11) . . ?
C12 C7 C6 122.24(11) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.18(11) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.85(11) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C13 118.77(11) . . ?
C11 C10 C9 120.03(12) . . ?
C11 C10 C13 121.20(11) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.96(12) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.73(12) . . ?
C11 C12 H12 119.6 . . ?
F1 C13 F2 106.46(11) . . ?
F1 C13 F3 106.39(11) . . ?
F1 C13 C10 112.99(11) . . ?
F2 C13 C10 112.26(11) . . ?
F3 C13 F2 106.13(11) . . ?
F3 C13 C10 112.11(10) . . ?
C15 C14 C3 119.82(11) . . ?
C15 C14 C19 118.24(12) . . ?
C19 C14 C3 121.92(11) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.39(12) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.42(12) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.17(12) . . ?
C16 C17 C20 120.84(12) . . ?
C18 C17 C20 118.97(12) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.98(12) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.79(12) . . ?
C18 C19 H19 119.6 . . ?
F4 C20 C17 111.55(11) . . ?
F5 C20 F4 106.04(11) . . ?
F5 C20 F6 107.13(11) . . ?
F5 C20 C17 112.19(11) . . ?
F6 C20 F4 106.27(11) . . ?
F6 C20 C17 113.19(11) . . ?

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 0.65(13) . . . . ?
S1 N1 C1 C6 -179.44(10) . . . . ?
S1 N2 C2 C1 1.05(13) . . . . ?
S1 N2 C2 C3 -179.96(10) . . . . ?
N1 S1 N2 C2 -0.61(10) . . . . ?
N1 C1 C2 N2 -1.16(15) . . . . ?
N1 C1 C2 C3 179.79(11) . . . . ?
N1 C1 C6 C5 -179.59(12) . . . . ?
N1 C1 C6 C7 0.84(19) . . . . ?
N2 S1 N1 C1 -0.03(10) . . . . ?
N2 C2 C3 C4 -179.40(12) . . . . ?
N2 C2 C3 C14 0.10(19) . . . . ?
C1 C2 C3 C4 -0.48(17) . . . . ?
C1 C2 C3 C14 179.02(11) . . . . ?
C1 C6 C7 C8 -149.52(12) . . . . ?
C1 C6 C7 C12 31.71(18) . . . . ?
C2 C1 C6 C5 0.31(17) . . . . ?
C2 C1 C6 C7 -179.26(11) . . . . ?
C2 C3 C4 C5 0.91(18) . . . . ?
C2 C3 C14 C15 -147.97(12) . . . . ?
C2 C3 C14 C19 33.67(18) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C3 C14 C15 C16 -177.50(12) . . . . ?
C3 C14 C19 C18 177.15(11) . . . . ?
C4 C3 C14 C15 31.51(18) . . . . ?
C4 C3 C14 C19 -146.86(13) . . . . ?
C4 C5 C6 C1 0.10(18) . . . . ?
C4 C5 C6 C7 179.68(11) . . . . ?
C5 C6 C7 C8 30.94(18) . . . . ?
C5 C6 C7 C12 -147.84(13) . . . . ?
C6 C1 C2 N2 178.93(11) . . . . ?
C6 C1 C2 C3 -0.12(18) . . . . ?
C6 C7 C8 C9 -178.14(11) . . . . ?
C6 C7 C12 C11 178.36(12) . . . . ?
C7 C8 C9 C10 -0.32(19) . . . . ?
C8 C7 C12 C11 -0.43(19) . . . . ?
C8 C9 C10 C11 -0.31(19) . . . . ?
C8 C9 C10 C13 179.85(11) . . . . ?
C9 C10 C11 C12 0.56(19) . . . . ?
C9 C10 C13 F1 -170.75(11) . . . . ?
C9 C10 C13 F2 68.83(15) . . . . ?
C9 C10 C13 F3 -50.54(16) . . . . ?
C10 C11 C12 C7 -0.2(2) . . . . ?
C11 C10 C13 F1 9.42(17) . . . . ?
C11 C10 C13 F2 -111.00(14) . . . . ?
C11 C10 C13 F3 129.63(13) . . . . ?
C12 C7 C8 C9 0.69(19) . . . . ?
C13 C10 C11 C12 -179.61(12) . . . . ?
C14 C3 C4 C5 -178.59(11) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C15 C14 C19 C18 -1.23(18) . . . . ?
C15 C16 C17 C18 -1.0(2) . . . . ?
C15 C16 C17 C20 -179.19(12) . . . . ?
C16 C17 C18 C19 0.64(19) . . . . ?
C16 C17 C20 F4 106.76(14) . . . . ?
C16 C17 C20 F5 -134.43(13) . . . . ?
C16 C17 C20 F6 -13.04(18) . . . . ?
C17 C18 C19 C14 0.47(19) . . . . ?
C18 C17 C20 F4 -71.49(15) . . . . ?
C18 C17 C20 F5 47.32(16) . . . . ?
C18 C17 C20 F6 168.71(12) . . . . ?
C19 C14 C15 C16 0.92(19) . . . . ?
C20 C17 C18 C19 178.91(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
####################################################################### 
# 
# 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_8v00439_0m
_database_code_depnum_ccdc_archive 'CCDC 2179280'
loop_
_audit_author_name
_audit_author_address
'Georgina Rosair'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_audit_creation_date             2022-06-14
_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         'C22 H12 N2 S5'
_chemical_formula_sum            'C22 H12 N2 S5'
_chemical_formula_weight         464.64
_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                   5.6980(2)
_cell_length_b                   31.4674(15)
_cell_length_c                   26.9001(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.599(3)
_cell_angle_gamma                90
_cell_volume                     4818.3(3)
_cell_formula_units_Z            10
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      70.043
_cell_measurement_theta_min      2.161
_shelx_estimated_absorpt_T_max   0.849
_shelx_estimated_absorpt_T_min   0.173
_exptl_absorpt_coefficient_mu    5.641
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1493 before and 0.1031 after correction.
The Ratio of minimum to maximum transmission is 0.7346.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2380
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1359
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            118988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.334
_diffrn_reflns_theta_min         2.162
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_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
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7368
_reflns_number_total             9129
_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 V8.40A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.981
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         9129
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0839
_refine_ls_restrained_S_all      1.177
_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)+(0.0001P)²+38.1216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1749
_refine_ls_wR_factor_ref         0.1827
_refine_special_details          disoreder
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{C46, C46A}
3. Restrained distances
 S13-C52 = S13-C54 = S13A-C52 = S13A-C55A
 1.75 with sigma of 0.02
 C53A-C52 = C53-C52 = C53-C55 = C55A-C54A = C54-C55 = C53A-C54A
 1.4 with sigma of 0.02
 C44A-C42A = C42A-C41 = C44A-C43 = C44-C43A = C43A-C42 = C42-C41
 1.4 with sigma of 0.02
 S10A-C41 = S10A-C43 = S10-C41 = S10-C44
 1.75 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(S13) = Uanis(C53) = Uanis(S13A) = Uanis(C52) = Uanis(C54A) = Uanis(C55) =
Uanis(C53A) = Uanis(C55A) = Uanis(C54)
Uanis(C46) = Uanis(C46A)
Uanis(C22) = Uanis(C19) = Uanis(C20) = Uanis(C21)
Uanis(C22A) = Uanis(C22)
Uanis(C41) = Uanis(C42) = Uanis(C43) = Uanis(C44) = Uanis(S10A) = Uanis(C43A) =
Uanis(C44A) = Uanis(S10) = Uanis(C42A)
5. Others
 Sof(C22A)=Sof(H22A)=1-FVAR(1)
 Sof(C22)=Sof(H22)=FVAR(1)
 Fixed Sof: S11(0.5) N5(0.5) N6(0.5) H45(0.5) S13(0.5) S14(0.5) C53(0.5)
 H53(0.5) C54(0.5) H54(0.5) C55(0.5) H55(0.5) S5(0.5) S13A(0.5) C53A(0.5)
 H53A(0.5) C54A(0.5) H54A(0.5) C55A(0.5) H55A(0.5) S10(0.5) C42(0.5) H42(0.5)
 C43A(0.5) H43A(0.5) C44(0.5) H44(0.5) S10A(0.5) C42A(0.5) H42A(0.5) C43(0.5)
 H43(0.5) C44A(0.5) H44A(0.5) C46(0.5) C46A(0.5) H46(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C20(H20), C21(H21), C22(H22), C49(H49), C50(H50), C53(H53), C54(H54),
  C55(H55), C53A(H53A), C54A(H54A), C55A(H55A), C26(H26), C27(H27), C30(H30),
 C31(H31), C34(H34), C35(H35), C36(H36), C38(H38), C39(H39), C42(H42),
 C43A(H43A), C44(H44), C42A(H42A), C43(H43), C44A(H44A), C46A(H46), C22A(H22A)
;
_atom_sites_solution_hydrogens   mixed
_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 1.3769(3) 0.64595(5) 0.74917(6) 0.0340(4) Uani 1 1 d . . . . .
S2 S 1.0879(3) 0.70555(5) 0.87934(6) 0.0295(3) Uani 1 1 d . . . . .
S3 S 0.9903(3) 0.78233(6) 1.01162(7) 0.0413(4) Uani 1 1 d . . . . .
S4 S 0.6970(3) 0.48962(5) 0.72719(6) 0.0312(3) Uani 1 1 d . . . . .
S11 S 0.3479(5) 0.41422(10) 0.52502(12) 0.0307(7) Uani 0.5 1 d . . P A 2
S12 S -0.2572(3) 0.39574(6) 0.42251(6) 0.0364(4) Uani 1 1 d . . . . .
N1 N 1.2193(9) 0.66193(17) 0.7937(2) 0.0312(12) Uani 1 1 d . . . . .
N2 N 1.2522(9) 0.60130(18) 0.7353(2) 0.0329(12) Uani 1 1 d . . . . .
N5 N -0.3758(17) 0.5384(3) 0.4529(4) 0.027(2) Uani 0.5 1 d . . P B 2
N6 N 0.117(2) 0.4192(5) 0.4891(6) 0.026(3) Uani 0.5 1 d . . P A 2
C1 C 1.0548(10) 0.6317(2) 0.8001(2) 0.0286(13) Uani 1 1 d . . . . .
C2 C 0.8760(10) 0.6335(2) 0.8364(2) 0.0281(13) Uani 1 1 d . . . . .
C3 C 0.7248(11) 0.5991(2) 0.8350(2) 0.0308(14) Uani 1 1 d . . . . .
H3 H 0.604825 0.598244 0.858425 0.037 Uiso 1 1 calc R U . . .
C4 C 0.7386(10) 0.5654(2) 0.8009(2) 0.0294(13) Uani 1 1 d . . . . .
H4 H 0.624218 0.543447 0.801650 0.035 Uiso 1 1 calc R U . . .
C5 C 0.9103(11) 0.5625(2) 0.7662(2) 0.0296(13) Uani 1 1 d . . . . .
C6 C 1.0723(11) 0.5969(2) 0.7663(2) 0.0304(14) Uani 1 1 d . . . . .
C7 C 0.8667(11) 0.6683(2) 0.8724(2) 0.0287(13) Uani 1 1 d . . . . .
C8 C 0.6997(11) 0.6742(2) 0.9070(2) 0.0304(14) Uani 1 1 d . . . . .
H8 H 0.563867 0.656845 0.909017 0.037 Uiso 1 1 calc R U . . .
C9 C 0.7513(11) 0.7086(2) 0.9391(3) 0.0341(15) Uani 1 1 d . . . . .
H9 H 0.652969 0.717219 0.964878 0.041 Uiso 1 1 calc R U . . .
C10 C 0.9582(11) 0.72834(19) 0.9293(2) 0.0305(14) Uani 1 1 d . . . . .
C12 C 1.2903(10) 0.78375(17) 0.9407(2) 0.0264(13) Uani 1 1 d . . . . .
H12 H 1.367896 0.778669 0.910782 0.032 Uiso 1 1 calc R U . . .
C13 C 1.3635(13) 0.8135(2) 0.9789(3) 0.0409(17) Uani 1 1 d . . . . .
H13 H 1.502637 0.829943 0.977034 0.049 Uiso 1 1 calc R U . . .
C14 C 1.2219(13) 0.8164(2) 1.0173(3) 0.0420(17) Uani 1 1 d . . . . .
H14 H 1.247933 0.835374 1.044489 0.050 Uiso 1 1 calc R U . . .
C15 C 0.9201(10) 0.5275(2) 0.7307(2) 0.0282(13) Uani 1 1 d . . . . .
C16 C 1.0815(11) 0.5192(2) 0.6953(2) 0.0333(14) Uani 1 1 d . . . . .
H16 H 1.217935 0.535968 0.691387 0.040 Uiso 1 1 calc R U . . .
C17 C 1.0260(11) 0.4835(2) 0.6657(3) 0.0326(14) Uani 1 1 d . . . . .
H17 H 1.120030 0.474057 0.639639 0.039 Uiso 1 1 calc R U . . .
C18 C 0.8227(11) 0.4638(2) 0.6781(2) 0.0324(14) Uani 1 1 d . . . . .
C19 C 0.7075(13) 0.4269(2) 0.6552(3) 0.0462(10) Uani 1 1 d . . . . .
C20 C 0.5043(13) 0.4062(2) 0.6689(3) 0.0462(10) Uani 1 1 d . . . . .
H20 H 0.414580 0.414239 0.696265 0.055 Uiso 1 1 calc R U . . .
C21 C 0.4488(13) 0.3719(2) 0.6368(3) 0.0462(10) Uani 1 1 d . . . . .
H21 H 0.345071 0.349411 0.644376 0.055 Uiso 1 1 calc R U . C 2
C22 C 0.632(3) 0.3598(6) 0.6081(7) 0.0462(10) Uani 0.51(2) 1 d . . P D 1
H22 H 0.636327 0.334319 0.589211 0.055 Uiso 0.51(2) 1 calc R U P D 1
C45 C 0.0451(11) 0.4575(2) 0.4918(2) 0.0310(14) Uani 1 1 d . . . . .
H45 H 0.07(4) 0.426(8) 0.490(10) 0.037 Uiso 0.5 1 d . U P E 1
C47 C -0.1532(11) 0.4745(2) 0.4665(2) 0.0319(14) Uani 1 1 d . . . . .
C48 C -0.3100(11) 0.4496(2) 0.4341(2) 0.0311(14) Uani 1 1 d . . . . .
C49 C -0.5136(12) 0.4619(2) 0.4084(3) 0.0382(16) Uani 1 1 d . . . . .
H49 H -0.572972 0.490040 0.409211 0.046 Uiso 1 1 calc R U . . .
C50 C -0.6253(12) 0.4292(2) 0.3810(3) 0.0408(17) Uani 1 1 d . . . . .
H50 H -0.767598 0.432848 0.361681 0.049 Uiso 1 1 calc R U . . .
C51 C -0.5073(12) 0.3917(2) 0.3852(2) 0.0390(16) Uani 1 1 d . . . . .
C52 C -0.5807(10) 0.3516(2) 0.3619(3) 0.0386(5) Uani 1 1 d D . . . .
C56 C 1.0812(11) 0.7631(2) 0.9554(2) 0.0322(14) Uani 1 1 d . . . . .
S13 S -0.4189(6) 0.30841(16) 0.3624(2) 0.0386(5) Uani 0.5 1 d D . P F 1
S14 S 0.8541(8) 0.39748(16) 0.61130(18) 0.0369(10) Uani 0.5 1 d . . P D 1
C53 C -0.804(4) 0.3455(8) 0.3345(12) 0.0386(5) Uani 0.5 1 d D . P F 1
H53 H -0.919448 0.367026 0.329615 0.046 Uiso 0.5 1 calc R U P F 1
C54 C -0.635(2) 0.2803(5) 0.3292(5) 0.0386(5) Uani 0.5 1 d D . P F 1
H54 H -0.619799 0.251105 0.320796 0.046 Uiso 0.5 1 calc R U P F 1
C55 C -0.828(2) 0.3040(5) 0.3163(6) 0.0386(5) Uani 0.5 1 d D . P F 1
H55 H -0.961760 0.293781 0.297528 0.046 Uiso 0.5 1 calc R U P F 1
S5 S 0.7892(9) 0.41050(16) 0.5959(2) 0.0432(11) Uani 0.5 1 d . . P D 2
S13A S -0.8341(10) 0.3436(2) 0.3305(3) 0.0386(5) Uani 0.5 1 d D . P F 2
C53A C -0.472(3) 0.3119(5) 0.3634(8) 0.0386(5) Uani 0.5 1 d D . P F 2
H53A H -0.336617 0.308030 0.384736 0.046 Uiso 0.5 1 calc R U P F 2
C54A C -0.554(2) 0.2781(5) 0.3351(5) 0.0386(5) Uani 0.5 1 d D . P F 2
H54A H -0.479123 0.251467 0.330525 0.046 Uiso 0.5 1 calc R U P F 2
C55A C -0.768(2) 0.2914(4) 0.3148(6) 0.0386(5) Uani 0.5 1 d D . P F 2
H55A H -0.868633 0.273968 0.294464 0.046 Uiso 0.5 1 calc R U P F 2
S6 S 0.5849(3) 0.95906(5) 0.55239(6) 0.0272(3) Uani 1 1 d . . . . .
S7 S 1.3389(3) 0.89851(5) 0.71415(6) 0.0310(3) Uani 1 1 d . . . . .
S8 S 1.2590(3) 0.76907(6) 0.77061(7) 0.0408(4) Uani 1 1 d . . . . .
S9 S 0.9152(2) 1.08149(5) 0.51315(6) 0.0261(3) Uani 1 1 d . . . . .
N3 N 0.7424(8) 1.00148(15) 0.54659(19) 0.0250(11) Uani 1 1 d . . . . .
N4 N 0.7247(8) 0.93577(16) 0.59791(18) 0.0256(11) Uani 1 1 d . . . . .
C23 C 0.9193(10) 0.99840(18) 0.5819(2) 0.0246(12) Uani 1 1 d . . . . .
C24 C 0.9093(10) 0.96040(18) 0.6113(2) 0.0243(12) Uani 1 1 d . . . . .
C25 C 1.0856(10) 0.95164(18) 0.6495(2) 0.0241(12) Uani 1 1 d . . . . .
C26 C 1.2545(10) 0.98284(19) 0.6573(2) 0.0294(13) Uani 1 1 d . . . . .
H26 H 1.370208 0.979056 0.683462 0.035 Uiso 1 1 calc R U . . .
C27 C 1.2624(10) 1.02024(19) 0.6279(2) 0.0284(13) Uani 1 1 d . . . . .
H27 H 1.383536 1.040267 0.635479 0.034 Uiso 1 1 calc R U . . .
C28 C 1.1047(10) 1.02908(19) 0.5892(2) 0.0261(13) Uani 1 1 d . . . . .
C29 C 1.0926(10) 0.91131(19) 0.6774(2) 0.0263(13) Uani 1 1 d . . . . .
C30 C 0.9326(11) 0.8787(2) 0.6772(2) 0.0317(14) Uani 1 1 d . . . . .
H30 H 0.785929 0.879664 0.658951 0.038 Uiso 1 1 calc R U . . .
C31 C 1.0059(11) 0.8438(2) 0.7063(2) 0.0326(14) Uani 1 1 d . . . . .
H31 H 0.914660 0.818805 0.709680 0.039 Uiso 1 1 calc R U . . .
C32 C 1.2248(11) 0.8496(2) 0.7296(2) 0.0311(14) Uani 1 1 d . . . . .
C33 C 1.3597(11) 0.8205(2) 0.7607(2) 0.0327(14) Uani 1 1 d . . . . .
C34 C 1.5701(12) 0.8265(3) 0.7862(3) 0.0476(19) Uani 1 1 d . . . . .
H34 H 1.653999 0.852554 0.785967 0.057 Uiso 1 1 calc R U . . .
C35 C 1.6512(13) 0.7903(3) 0.8127(3) 0.052(2) Uani 1 1 d . . . . .
H35 H 1.794274 0.789449 0.832262 0.062 Uiso 1 1 calc R U . . .
C36 C 1.5017(12) 0.7570(2) 0.8072(3) 0.0447(18) Uani 1 1 d . . . . .
H36 H 1.529038 0.729946 0.822117 0.054 Uiso 1 1 calc R U . . .
C37 C 1.1270(10) 1.06645(19) 0.5576(2) 0.0248(12) Uani 1 1 d . . . . .
C38 C 1.3123(11) 1.09456(19) 0.5579(2) 0.0291(13) Uani 1 1 d . . . . .
H38 H 1.448235 1.091553 0.579360 0.035 Uiso 1 1 calc R U . . .
C39 C 1.2835(11) 1.12784(19) 0.5238(2) 0.0298(14) Uani 1 1 d . . . . .
H39 H 1.395644 1.149825 0.520071 0.036 Uiso 1 1 calc R U . . .
C40 C 1.0753(10) 1.12526(18) 0.4963(2) 0.0267(13) Uani 1 1 d . . . . .
C41 C 0.9834(11) 1.15429(19) 0.4589(3) 0.0338(5) Uani 1 1 d D . . . .
S10 S 1.1225(10) 1.19872(18) 0.4409(3) 0.0338(5) Uani 0.5 1 d D . P G 1
C42 C 0.763(3) 1.1586(5) 0.4350(6) 0.0338(5) Uani 0.5 1 d D . P G 1
H42 H 0.640996 1.141683 0.447439 0.041 Uiso 0.5 1 calc R U P G 1
C43A C 0.703(2) 1.1842(4) 0.3956(6) 0.0338(5) Uani 0.5 1 d D . P G 1
H43A H 0.571499 1.183464 0.372745 0.041 Uiso 0.5 1 calc R U P G 1
C44 C 0.890(2) 1.2114(4) 0.3990(6) 0.0338(5) Uani 0.5 1 d D . P G 1
H44 H 0.894149 1.236306 0.379192 0.041 Uiso 0.5 1 calc R U P G 1
S10A S 0.7293(7) 1.14730(10) 0.43034(16) 0.0338(5) Uani 0.5 1 d D . P G 2
C42A C 1.101(4) 1.1937(7) 0.4420(12) 0.0338(5) Uani 0.5 1 d D . P G 2
H42A H 1.256205 1.201988 0.452133 0.041 Uiso 0.5 1 calc R U P G 2
C43 C 0.750(2) 1.1947(4) 0.3994(6) 0.0338(5) Uani 0.5 1 d D . P G 2
H43 H 0.628548 1.204778 0.377072 0.041 Uiso 0.5 1 calc R U P G 2
C44A C 0.951(2) 1.2169(5) 0.4090(6) 0.0338(5) Uani 0.5 1 d D . P G 2
H44A H 0.985948 1.243936 0.395507 0.041 Uiso 0.5 1 calc R U P G 2
C46 C -0.1965(11) 0.5179(2) 0.4754(2) 0.0325(14) Uani 0.5 1 d . . P B .
C46A C -0.1965(11) 0.5179(2) 0.4754(2) 0.0325(14) Uani 0.5 1 d . . P H 1
H46 H -0.328910 0.531136 0.459184 0.039 Uiso 0.5 1 calc R U P H 1
C22A C 0.568(3) 0.3753(6) 0.5916(8) 0.0462(10) Uani 0.49(2) 1 d . . P D 2
H22A H 0.527775 0.359493 0.562403 0.055 Uiso 0.49(2) 1 calc R U P D 2


_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 1.611(5) . ?
S1 N2 1.611(6) . ?
S2 C7 1.725(7) . ?
S2 C10 1.720(6) . ?
S3 C14 1.703(8) . ?
S3 C56 1.729(7) . ?
S4 C15 1.742(6) . ?
S4 C18 1.732(6) . ?
S11 N5 1.611(11) 3_566 ?
S11 N6 1.606(16) . ?
S12 C48 1.751(7) . ?
S12 C51 1.711(7) . ?
N1 C1 1.351(8) . ?
N2 C6 1.357(8) . ?
N5 C46 1.330(11) . ?
N6 C45 1.275(17) . ?
C1 C2 1.443(8) . ?
C1 C6 1.432(9) . ?
C2 C3 1.381(9) . ?
C2 C7 1.466(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.410(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(8) . ?
C5 C6 1.423(9) . ?
C5 C15 1.459(9) . ?
C7 C8 1.372(9) . ?
C8 H8 0.9500 . ?
C8 C9 1.409(10) . ?
C9 H9 0.9500 . ?
C9 C10 1.369(9) . ?
C10 C56 1.462(10) . ?
C12 H12 0.9500 . ?
C12 C13 1.436(10) . ?
C12 C56 1.429(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.343(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(9) . ?
C16 H16 0.9500 . ?
C16 C17 1.403(9) . ?
C17 H17 0.9500 . ?
C17 C18 1.369(9) . ?
C18 C19 1.457(10) . ?
C19 C20 1.392(10) . ?
C19 S14 1.742(9) . ?
C19 S5 1.758(9) . ?
C20 H20 0.9500 . ?
C20 C21 1.409(10) . ?
C21 H21 0.9500 . ?
C21 C22 1.382(17) . ?
C21 C22A 1.425(18) . ?
C22 H22 0.9500 . ?
C22 S14 1.732(16) . ?
C45 H45 1.0(3) . ?
C45 C47 1.399(9) . ?
C45 C46 1.433(10) 3_566 ?
C47 C48 1.450(9) . ?
C47 C46 1.410(9) . ?
C48 C49 1.378(9) . ?
C49 H49 0.9500 . ?
C49 C50 1.400(10) . ?
C50 H50 0.9500 . ?
C50 C51 1.361(10) . ?
C51 C52 1.461(10) . ?
C52 S13 1.642(8) . ?
C52 C53 1.453(16) . ?
C52 S13A 1.658(8) . ?
C52 C53A 1.393(15) . ?
S13 C54 1.730(12) . ?
C53 H53 0.9500 . ?
C53 C55 1.398(18) . ?
C54 H54 0.9500 . ?
C54 C55 1.365(14) . ?
C55 H55 0.9500 . ?
S5 C22A 1.675(17) . ?
S13A C55A 1.742(13) . ?
C53A H53A 0.9500 . ?
C53A C54A 1.377(16) . ?
C54A H54A 0.9500 . ?
C54A C55A 1.378(14) . ?
C55A H55A 0.9500 . ?
S6 N3 1.620(5) . ?
S6 N4 1.607(5) . ?
S7 C29 1.728(6) . ?
S7 C32 1.728(6) . ?
S8 C33 1.741(7) . ?
S8 C36 1.704(8) . ?
S9 C37 1.726(6) . ?
S9 C40 1.724(6) . ?
N3 C23 1.356(8) . ?
N4 C24 1.342(7) . ?
C23 C24 1.436(8) . ?
C23 C28 1.438(8) . ?
C24 C25 1.431(8) . ?
C25 C26 1.384(8) . ?
C25 C29 1.474(8) . ?
C26 H26 0.9500 . ?
C26 C27 1.419(9) . ?
C27 H27 0.9500 . ?
C27 C28 1.372(9) . ?
C28 C37 1.460(9) . ?
C29 C30 1.373(9) . ?
C30 H30 0.9500 . ?
C30 C31 1.401(9) . ?
C31 H31 0.9500 . ?
C31 C32 1.382(9) . ?
C32 C33 1.440(9) . ?
C33 C34 1.367(10) . ?
C34 H34 0.9500 . ?
C34 C35 1.410(10) . ?
C35 H35 0.9500 . ?
C35 C36 1.356(11) . ?
C36 H36 0.9500 . ?
C37 C38 1.377(8) . ?
C38 H38 0.9500 . ?
C38 C39 1.396(9) . ?
C39 H39 0.9500 . ?
C39 C40 1.371(9) . ?
C40 C41 1.441(9) . ?
C41 S10 1.688(7) . ?
C41 C42 1.389(14) . ?
C41 S10A 1.623(7) . ?
C41 C42A 1.489(16) . ?
S10 C44 1.744(12) . ?
C42 H42 0.9500 . ?
C42 C43A 1.362(15) . ?
C43A H43A 0.9500 . ?
C43A C44 1.365(14) . ?
C44 H44 0.9500 . ?
S10A C43 1.714(12) . ?
C42A H42A 0.9500 . ?
C42A C44A 1.407(18) . ?
C43 H43 0.9500 . ?
C43 C44A 1.358(14) . ?
C44A H44A 0.9500 . ?
C22A H22A 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 101.0(3) . . ?
C10 S2 C7 91.7(3) . . ?
C14 S3 C56 92.1(3) . . ?
C18 S4 C15 92.1(3) . . ?
C51 S12 C48 91.8(3) . . ?
C1 N1 S1 106.8(4) . . ?
C6 N2 S1 106.5(5) . . ?
C46 N5 S11 102.7(7) . 3_566 ?
C45 N6 S11 108.3(13) . . ?
N1 C1 C2 125.1(6) . . ?
N1 C1 C6 112.9(5) . . ?
C6 C1 C2 122.1(6) . . ?
C1 C2 C7 121.5(6) . . ?
C3 C2 C1 114.3(6) . . ?
C3 C2 C7 124.1(6) . . ?
C2 C3 H3 118.2 . . ?
C2 C3 C4 123.6(6) . . ?
C4 C3 H3 118.2 . . ?
C3 C4 H4 118.3 . . ?
C5 C4 C3 123.4(6) . . ?
C5 C4 H4 118.3 . . ?
C4 C5 C6 115.3(6) . . ?
C4 C5 C15 122.6(6) . . ?
C6 C5 C15 122.0(6) . . ?
N2 C6 C1 112.9(6) . . ?
N2 C6 C5 125.8(6) . . ?
C5 C6 C1 121.3(6) . . ?
C2 C7 S2 122.1(4) . . ?
C8 C7 S2 111.2(5) . . ?
C8 C7 C2 126.5(6) . . ?
C7 C8 H8 123.6 . . ?
C7 C8 C9 112.8(6) . . ?
C9 C8 H8 123.6 . . ?
C8 C9 H9 123.6 . . ?
C10 C9 C8 112.8(6) . . ?
C10 C9 H9 123.6 . . ?
C9 C10 S2 111.5(5) . . ?
C9 C10 C56 130.2(6) . . ?
C56 C10 S2 118.3(5) . . ?
C13 C12 H12 125.7 . . ?
C56 C12 H12 125.7 . . ?
C56 C12 C13 108.5(6) . . ?
C12 C13 H13 122.3 . . ?
C14 C13 C12 115.4(7) . . ?
C14 C13 H13 122.3 . . ?
S3 C14 H14 123.9 . . ?
C13 C14 S3 112.2(6) . . ?
C13 C14 H14 123.9 . . ?
C5 C15 S4 120.1(5) . . ?
C16 C15 S4 109.9(5) . . ?
C16 C15 C5 129.9(6) . . ?
C15 C16 H16 123.1 . . ?
C15 C16 C17 113.8(6) . . ?
C17 C16 H16 123.1 . . ?
C16 C17 H17 123.3 . . ?
C18 C17 C16 113.3(6) . . ?
C18 C17 H17 123.3 . . ?
C17 C18 S4 110.9(5) . . ?
C17 C18 C19 128.9(6) . . ?
C19 C18 S4 120.2(5) . . ?
C18 C19 S14 119.3(5) . . ?
C18 C19 S5 119.0(5) . . ?
C20 C19 C18 128.6(7) . . ?
C20 C19 S14 111.2(6) . . ?
C20 C19 S5 111.1(6) . . ?
C19 C20 H20 124.4 . . ?
C19 C20 C21 111.3(7) . . ?
C21 C20 H20 124.4 . . ?
C20 C21 H21 124.4 . . ?
C20 C21 C22A 111.2(9) . . ?
C22 C21 C20 113.5(9) . . ?
C22A C21 H21 124.4 . . ?
C21 C22 H22 124.7 . . ?
C21 C22 S14 110.6(11) . . ?
S14 C22 H22 124.7 . . ?
N6 C45 C47 125.9(10) . . ?
N6 C45 C46 111.1(9) . 3_566 ?
C47 C45 H45 119(10) . . ?
C47 C45 C46 123.0(7) . 3_566 ?
C46 C45 H45 117(10) 3_566 . ?
C45 C47 C48 123.3(6) . . ?
C45 C47 C46 115.5(6) . . ?
C46 C47 C48 121.2(6) . . ?
C47 C48 S12 121.6(5) . . ?
C49 C48 S12 109.3(5) . . ?
C49 C48 C47 129.2(6) . . ?
C48 C49 H49 122.9 . . ?
C48 C49 C50 114.2(7) . . ?
C50 C49 H49 122.9 . . ?
C49 C50 H50 123.8 . . ?
C51 C50 C49 112.4(6) . . ?
C51 C50 H50 123.8 . . ?
C50 C51 S12 112.3(6) . . ?
C50 C51 C52 125.6(6) . . ?
C52 C51 S12 122.1(6) . . ?
C51 C52 S13 124.1(5) . . ?
C51 C52 S13A 125.1(6) . . ?
C53 C52 C51 124.0(11) . . ?
C53 C52 S13 111.9(11) . . ?
C53A C52 C51 130.1(10) . . ?
C53A C52 S13A 104.7(9) . . ?
C10 C56 S3 121.7(5) . . ?
C12 C56 S3 111.7(5) . . ?
C12 C56 C10 126.5(6) . . ?
C52 S13 C54 91.9(6) . . ?
C22 S14 C19 91.5(6) . . ?
C52 C53 H53 124.1 . . ?
C55 C53 C52 111.8(19) . . ?
C55 C53 H53 124.1 . . ?
S13 C54 H54 123.3 . . ?
C55 C54 S13 113.5(12) . . ?
C55 C54 H54 123.3 . . ?
C53 C55 H55 124.6 . . ?
C54 C55 C53 110.8(17) . . ?
C54 C55 H55 124.6 . . ?
C22A S5 C19 91.6(7) . . ?
C52 S13A C55A 94.2(6) . . ?
C52 C53A H53A 118.7 . . ?
C54A C53A C52 122.6(16) . . ?
C54A C53A H53A 118.7 . . ?
C53A C54A H54A 127.7 . . ?
C53A C54A C55A 104.7(15) . . ?
C55A C54A H54A 127.7 . . ?
S13A C55A H55A 123.6 . . ?
C54A C55A S13A 112.9(12) . . ?
C54A C55A H55A 123.6 . . ?
N4 S6 N3 101.0(3) . . ?
C32 S7 C29 92.3(3) . . ?
C36 S8 C33 91.8(4) . . ?
C40 S9 C37 92.2(3) . . ?
C23 N3 S6 105.7(4) . . ?
C24 N4 S6 107.2(4) . . ?
N3 C23 C24 113.5(5) . . ?
N3 C23 C28 124.5(6) . . ?
C24 C23 C28 122.0(5) . . ?
N4 C24 C23 112.6(5) . . ?
N4 C24 C25 126.6(5) . . ?
C25 C24 C23 120.8(5) . . ?
C24 C25 C29 122.3(5) . . ?
C26 C25 C24 115.7(5) . . ?
C26 C25 C29 122.0(6) . . ?
C25 C26 H26 118.6 . . ?
C25 C26 C27 122.9(6) . . ?
C27 C26 H26 118.6 . . ?
C26 C27 H27 118.2 . . ?
C28 C27 C26 123.7(6) . . ?
C28 C27 H27 118.2 . . ?
C23 C28 C37 122.9(5) . . ?
C27 C28 C23 114.8(6) . . ?
C27 C28 C37 122.3(5) . . ?
C25 C29 S7 119.7(4) . . ?
C30 C29 S7 110.5(5) . . ?
C30 C29 C25 129.7(6) . . ?
C29 C30 H30 123.1 . . ?
C29 C30 C31 113.7(6) . . ?
C31 C30 H30 123.1 . . ?
C30 C31 H31 123.5 . . ?
C32 C31 C30 112.9(6) . . ?
C32 C31 H31 123.5 . . ?
C31 C32 S7 110.5(5) . . ?
C31 C32 C33 128.7(6) . . ?
C33 C32 S7 120.6(5) . . ?
C32 C33 S8 120.7(5) . . ?
C34 C33 S8 109.8(5) . . ?
C34 C33 C32 129.5(7) . . ?
C33 C34 H34 123.1 . . ?
C33 C34 C35 113.8(7) . . ?
C35 C34 H34 123.1 . . ?
C34 C35 H35 123.9 . . ?
C36 C35 C34 112.3(7) . . ?
C36 C35 H35 123.9 . . ?
S8 C36 H36 123.8 . . ?
C35 C36 S8 112.3(6) . . ?
C35 C36 H36 123.8 . . ?
C28 C37 S9 123.2(4) . . ?
C38 C37 S9 109.8(5) . . ?
C38 C37 C28 127.0(6) . . ?
C37 C38 H38 122.9 . . ?
C37 C38 C39 114.3(6) . . ?
C39 C38 H38 122.9 . . ?
C38 C39 H39 123.8 . . ?
C40 C39 C38 112.5(6) . . ?
C40 C39 H39 123.8 . . ?
C39 C40 S9 111.2(5) . . ?
C39 C40 C41 128.1(6) . . ?
C41 C40 S9 120.7(5) . . ?
C40 C41 S10 124.4(5) . . ?
C40 C41 S10A 122.2(5) . . ?
C40 C41 C42A 125.9(11) . . ?
C42 C41 C40 132.6(8) . . ?
C42 C41 S10 102.3(7) . . ?
C42A C41 S10A 111.9(10) . . ?
C41 S10 C44 91.2(6) . . ?
C41 C42 H42 116.3 . . ?
C43A C42 C41 127.3(14) . . ?
C43A C42 H42 116.3 . . ?
C42 C43A H43A 130.7 . . ?
C42 C43A C44 98.7(13) . . ?
C44 C43A H43A 130.7 . . ?
S10 C44 H44 121.1 . . ?
C43A C44 S10 117.8(11) . . ?
C43A C44 H44 121.1 . . ?
C41 S10A C43 91.8(5) . . ?
C41 C42A H42A 124.6 . . ?
C44A C42A C41 110.8(16) . . ?
C44A C42A H42A 124.6 . . ?
S10A C43 H43 122.2 . . ?
C44A C43 S10A 115.5(11) . . ?
C44A C43 H43 122.2 . . ?
C42A C44A H44A 125.2 . . ?
C43 C44A C42A 109.6(15) . . ?
C43 C44A H44A 125.2 . . ?
N5 C46 C47 121.9(7) . . ?
C47 C46 C45 121.5(6) . 3_566 ?
C21 C22A S5 112.2(12) . . ?
C21 C22A H22A 123.9 . . ?
S5 C22A H22A 123.9 . . ?

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 -179.8(5) . . . . ?
S1 N1 C1 C6 -0.4(6) . . . . ?
S1 N2 C6 C1 -0.7(7) . . . . ?
S1 N2 C6 C5 178.3(5) . . . . ?
S2 C7 C8 C9 -0.3(7) . . . . ?
S2 C10 C56 S3 -169.5(3) . . . . ?
S2 C10 C56 C12 7.2(8) . . . . ?
S4 C15 C16 C17 0.8(7) . . . . ?
S4 C18 C19 C20 -3.9(12) . . . . ?
S4 C18 C19 S14 -172.0(4) . . . . ?
S4 C18 C19 S5 162.3(5) . . . . ?
S11 N5 C46 C45 -1.4(9) 3_566 . . 3_566 ?
S11 N5 C46 C47 -179.9(6) 3_566 . . . ?
S11 N6 C45 C47 -179.2(6) . . . . ?
S11 N6 C45 C46 1.0(12) . . . 3_566 ?
S12 C48 C49 C50 0.8(7) . . . . ?
S12 C51 C52 S13 -8.4(9) . . . . ?
S12 C51 C52 C53 172.8(18) . . . . ?
S12 C51 C52 S13A 172.8(5) . . . . ?
S12 C51 C52 C53A -1.8(15) . . . . ?
N1 S1 N2 C6 0.4(5) . . . . ?
N1 C1 C2 C3 178.7(6) . . . . ?
N1 C1 C2 C7 -3.7(9) . . . . ?
N1 C1 C6 N2 0.7(8) . . . . ?
N1 C1 C6 C5 -178.2(5) . . . . ?
N2 S1 N1 C1 0.1(5) . . . . ?
N5 S11 N6 C45 -0.2(11) 3_566 . . . ?
N6 C45 C47 C48 1.6(13) . . . . ?
N6 C45 C47 C46 -179.8(10) . . . . ?
C1 C2 C3 C4 -1.0(9) . . . . ?
C1 C2 C7 S2 -8.5(8) . . . . ?
C1 C2 C7 C8 177.0(6) . . . . ?
C2 C1 C6 N2 -179.9(5) . . . . ?
C2 C1 C6 C5 1.2(9) . . . . ?
C2 C3 C4 C5 2.2(10) . . . . ?
C2 C7 C8 C9 174.7(6) . . . . ?
C3 C2 C7 S2 168.9(5) . . . . ?
C3 C2 C7 C8 -5.7(10) . . . . ?
C3 C4 C5 C6 -1.5(9) . . . . ?
C3 C4 C5 C15 -179.2(6) . . . . ?
C4 C5 C6 N2 -178.9(6) . . . . ?
C4 C5 C6 C1 -0.1(9) . . . . ?
C4 C5 C15 S4 5.4(8) . . . . ?
C4 C5 C15 C16 -177.5(6) . . . . ?
C5 C15 C16 C17 -176.5(6) . . . . ?
C6 C1 C2 C3 -0.6(8) . . . . ?
C6 C1 C2 C7 177.0(6) . . . . ?
C6 C5 C15 S4 -172.1(5) . . . . ?
C6 C5 C15 C16 4.9(10) . . . . ?
C7 S2 C10 C9 -1.5(5) . . . . ?
C7 S2 C10 C56 176.2(5) . . . . ?
C7 C2 C3 C4 -178.6(6) . . . . ?
C7 C8 C9 C10 -0.8(8) . . . . ?
C8 C9 C10 S2 1.6(7) . . . . ?
C8 C9 C10 C56 -175.8(6) . . . . ?
C9 C10 C56 S3 7.7(9) . . . . ?
C9 C10 C56 C12 -175.7(6) . . . . ?
C10 S2 C7 C2 -174.3(5) . . . . ?
C10 S2 C7 C8 1.0(5) . . . . ?
C12 C13 C14 S3 1.7(8) . . . . ?
C13 C12 C56 S3 1.9(6) . . . . ?
C13 C12 C56 C10 -175.1(6) . . . . ?
C14 S3 C56 C10 176.2(5) . . . . ?
C14 S3 C56 C12 -0.9(5) . . . . ?
C15 S4 C18 C17 0.3(5) . . . . ?
C15 S4 C18 C19 -178.2(6) . . . . ?
C15 C5 C6 N2 -1.2(10) . . . . ?
C15 C5 C6 C1 177.6(6) . . . . ?
C15 C16 C17 C18 -0.6(8) . . . . ?
C16 C17 C18 S4 0.1(7) . . . . ?
C16 C17 C18 C19 178.4(7) . . . . ?
C17 C18 C19 C20 178.0(8) . . . . ?
C17 C18 C19 S14 9.8(11) . . . . ?
C17 C18 C19 S5 -15.9(11) . . . . ?
C18 S4 C15 C5 177.0(5) . . . . ?
C18 S4 C15 C16 -0.6(5) . . . . ?
C18 C19 C20 C21 179.5(8) . . . . ?
C18 C19 S14 C22 174.2(10) . . . . ?
C18 C19 S5 C22A -171.5(10) . . . . ?
C19 C20 C21 C22 15.5(15) . . . . ?
C19 C20 C21 C22A -17.7(14) . . . . ?
C19 S5 C22A C21 -7.0(15) . . . . ?
C20 C19 S14 C22 4.1(10) . . . . ?
C20 C19 S5 C22A -3.1(11) . . . . ?
C20 C21 C22 S14 -12.2(18) . . . . ?
C20 C21 C22A S5 15.4(18) . . . . ?
C21 C22 S14 C19 4.5(14) . . . . ?
C45 C47 C48 S12 -1.9(9) . . . . ?
C45 C47 C48 C49 177.7(6) . . . . ?
C45 C47 C46 N5 178.4(7) . . . . ?
C45 C47 C46 C45 0.0(10) . . . 3_566 ?
C47 C48 C49 C50 -178.8(6) . . . . ?
C48 S12 C51 C50 0.6(5) . . . . ?
C48 S12 C51 C52 -178.5(6) . . . . ?
C48 C47 C46 N5 -3.0(11) . . . . ?
C48 C47 C46 C45 178.6(6) . . . 3_566 ?
C48 C49 C50 C51 -0.4(9) . . . . ?
C49 C50 C51 S12 -0.2(8) . . . . ?
C49 C50 C51 C52 178.9(6) . . . . ?
C50 C51 C52 S13 172.6(6) . . . . ?
C50 C51 C52 C53 -6(2) . . . . ?
C50 C51 C52 S13A -6.2(11) . . . . ?
C50 C51 C52 C53A 179.2(13) . . . . ?
C51 S12 C48 C47 178.9(5) . . . . ?
C51 S12 C48 C49 -0.8(5) . . . . ?
C51 C52 S13 C54 179.5(8) . . . . ?
C51 C52 C53 C55 -179.8(15) . . . . ?
C51 C52 S13A C55A 177.4(8) . . . . ?
C51 C52 C53A C54A -173.4(13) . . . . ?
C52 S13 C54 C55 1.8(12) . . . . ?
C52 C53 C55 C54 0(3) . . . . ?
C52 S13A C55A C54A 2.7(12) . . . . ?
C52 C53A C54A C55A -9(2) . . . . ?
C56 S3 C14 C13 -0.4(6) . . . . ?
C56 C12 C13 C14 -2.3(8) . . . . ?
S13 C52 C53 C55 1(3) . . . . ?
S13 C54 C55 C53 -1(2) . . . . ?
S14 C19 C20 C21 -11.6(10) . . . . ?
C53 C52 S13 C54 -1.7(18) . . . . ?
S5 C19 C20 C21 12.4(10) . . . . ?
S13A C52 C53A C54A 11(2) . . . . ?
C53A C52 S13A C55A -6.9(13) . . . . ?
C53A C54A C55A S13A 2.7(17) . . . . ?
S6 N3 C23 C24 0.1(6) . . . . ?
S6 N3 C23 C28 178.5(5) . . . . ?
S6 N4 C24 C23 0.6(6) . . . . ?
S6 N4 C24 C25 -178.4(5) . . . . ?
S7 C29 C30 C31 0.2(7) . . . . ?
S7 C32 C33 S8 -172.8(4) . . . . ?
S7 C32 C33 C34 7.5(11) . . . . ?
S8 C33 C34 C35 0.7(9) . . . . ?
S9 C37 C38 C39 1.1(7) . . . . ?
S9 C40 C41 S10 178.2(5) . . . . ?
S9 C40 C41 C42 9.9(14) . . . . ?
S9 C40 C41 S10A -0.7(8) . . . . ?
S9 C40 C41 C42A 178.4(18) . . . . ?
N3 S6 N4 C24 -0.5(4) . . . . ?
N3 C23 C24 N4 -0.5(7) . . . . ?
N3 C23 C24 C25 178.6(5) . . . . ?
N3 C23 C28 C27 178.4(5) . . . . ?
N3 C23 C28 C37 -2.6(9) . . . . ?
N4 S6 N3 C23 0.3(4) . . . . ?
N4 C24 C25 C26 -177.9(6) . . . . ?
N4 C24 C25 C29 4.4(9) . . . . ?
C23 C24 C25 C26 3.2(8) . . . . ?
C23 C24 C25 C29 -174.5(5) . . . . ?
C23 C28 C37 S9 8.3(8) . . . . ?
C23 C28 C37 C38 -171.4(6) . . . . ?
C24 C23 C28 C27 -3.2(8) . . . . ?
C24 C23 C28 C37 175.8(5) . . . . ?
C24 C25 C26 C27 -3.3(9) . . . . ?
C24 C25 C29 S7 167.6(5) . . . . ?
C24 C25 C29 C30 -7.9(10) . . . . ?
C25 C26 C27 C28 0.0(10) . . . . ?
C25 C29 C30 C31 176.1(6) . . . . ?
C26 C25 C29 S7 -10.0(8) . . . . ?
C26 C25 C29 C30 174.5(6) . . . . ?
C26 C27 C28 C23 3.3(9) . . . . ?
C26 C27 C28 C37 -175.8(6) . . . . ?
C27 C28 C37 S9 -172.7(5) . . . . ?
C27 C28 C37 C38 7.5(9) . . . . ?
C28 C23 C24 N4 -179.0(5) . . . . ?
C28 C23 C24 C25 0.1(9) . . . . ?
C28 C37 C38 C39 -179.1(6) . . . . ?
C29 S7 C32 C31 0.7(5) . . . . ?
C29 S7 C32 C33 177.8(6) . . . . ?
C29 C25 C26 C27 174.4(6) . . . . ?
C29 C30 C31 C32 0.3(9) . . . . ?
C30 C31 C32 S7 -0.7(7) . . . . ?
C30 C31 C32 C33 -177.5(6) . . . . ?
C31 C32 C33 S8 3.7(10) . . . . ?
C31 C32 C33 C34 -176.0(8) . . . . ?
C32 S7 C29 C25 -176.9(5) . . . . ?
C32 S7 C29 C30 -0.5(5) . . . . ?
C32 C33 C34 C35 -179.6(7) . . . . ?
C33 S8 C36 C35 1.1(6) . . . . ?
C33 C34 C35 C36 0.1(11) . . . . ?
C34 C35 C36 S8 -0.9(9) . . . . ?
C36 S8 C33 C32 179.2(6) . . . . ?
C36 S8 C33 C34 -1.0(6) . . . . ?
C37 S9 C40 C39 0.3(5) . . . . ?
C37 S9 C40 C41 -177.9(5) . . . . ?
C37 C38 C39 C40 -0.9(8) . . . . ?
C38 C39 C40 S9 0.2(7) . . . . ?
C38 C39 C40 C41 178.3(6) . . . . ?
C39 C40 C41 S10 0.3(10) . . . . ?
C39 C40 C41 C42 -167.9(12) . . . . ?
C39 C40 C41 S10A -178.6(6) . . . . ?
C39 C40 C41 C42A 0(2) . . . . ?
C40 S9 C37 C28 179.4(5) . . . . ?
C40 S9 C37 C38 -0.8(5) . . . . ?
C40 C41 S10 C44 -179.1(8) . . . . ?
C40 C41 C42 C43A -171.6(13) . . . . ?
C40 C41 S10A C43 175.4(8) . . . . ?
C40 C41 C42A C44A -173.5(15) . . . . ?
C41 S10 C44 C43A -0.5(14) . . . . ?
C41 C42 C43A C44 -18(2) . . . . ?
C41 S10A C43 C44A 1.2(13) . . . . ?
C41 C42A C44A C43 -5(3) . . . . ?
S10 C41 C42 C43A 18(2) . . . . ?
C42 C41 S10 C44 -7.9(12) . . . . ?
C42 C43A C44 S10 8.7(17) . . . . ?
S10A C41 C42A C44A 6(3) . . . . ?
S10A C43 C44A C42A 2(2) . . . . ?
C42A C41 S10A C43 -3.8(18) . . . . ?
C46 C45 C47 C48 -178.6(6) 3_566 . . . ?
C46 C45 C47 C46 -0.1(10) 3_566 . . . ?
C46 C47 C48 S12 179.6(5) . . . . ?
C46 C47 C48 C49 -0.8(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
####################################################################### 
# 
# 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_8v00601_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2179284'
loop_
_audit_author_name
_audit_author_address
'Georgina Rosair'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_audit_creation_date             2022-06-14
_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         'C20 H23 N'
_chemical_formula_sum            'C20 H23 N'
_chemical_formula_weight         277.39
_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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5737(2)
_cell_length_b                   10.6100(3)
_cell_length_c                   11.3773(3)
_cell_angle_alpha                73.1270(10)
_cell_angle_beta                 88.4100(10)
_cell_angle_gamma                77.2260(10)
_cell_volume                     740.01(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8233
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.030
_cell_measurement_theta_min      4.064
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1006 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8725.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15951
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.054
_diffrn_reflns_theta_min         4.063
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8Venture'
_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
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2537
_reflns_number_total             2881
_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 (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2881
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.076
_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)+(0.0517P)²+0.2089P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1090
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C16(H16), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C17(H17A,H17B), C19(H19A,H19B), C20(H20A,
 H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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
N1 N 0.31914(14) 0.79919(9) 0.54797(8) 0.0182(2) Uani 1 1 d . . . . .
C2 C 0.25783(17) 0.78219(10) 0.44054(10) 0.0183(2) Uani 1 1 d . . . . .
C3 C 0.05069(18) 0.84426(11) 0.39462(10) 0.0209(2) Uani 1 1 d . . . . .
H3 H -0.040187 0.896460 0.437948 0.025 Uiso 1 1 calc R U . . .
C4 C -0.01979(19) 0.82961(11) 0.28813(11) 0.0243(3) Uani 1 1 d . . . . .
H4 H -0.159653 0.870875 0.258822 0.029 Uiso 1 1 calc R U . . .
C5 C 0.11363(19) 0.75373(12) 0.22155(11) 0.0245(3) Uani 1 1 d . . . . .
H5 H 0.064260 0.745920 0.146855 0.029 Uiso 1 1 calc R U . . .
C6 C 0.31400(18) 0.69144(11) 0.26458(10) 0.0217(2) Uani 1 1 d . . . . .
H6 H 0.402076 0.639306 0.220057 0.026 Uiso 1 1 calc R U . . .
C7 C 0.39173(17) 0.70381(11) 0.37490(10) 0.0184(2) Uani 1 1 d . . . . .
C8 C 0.59805(18) 0.64129(11) 0.42394(10) 0.0202(2) Uani 1 1 d . . . . .
C9 C 0.65466(17) 0.66141(11) 0.53117(10) 0.0203(2) Uani 1 1 d . . . . .
H9 H 0.792192 0.621711 0.565408 0.024 Uiso 1 1 calc R U . . .
C10 C 0.51197(17) 0.74020(11) 0.59175(10) 0.0175(2) Uani 1 1 d . . . . .
C11 C 0.74873(18) 0.55464(12) 0.36197(11) 0.0250(3) Uani 1 1 d . . . . .
H11A H 0.696568 0.474568 0.363346 0.038 Uiso 1 1 calc R U . . .
H11B H 0.885236 0.526497 0.405545 0.038 Uiso 1 1 calc R U . . .
H11C H 0.762651 0.606342 0.276617 0.038 Uiso 1 1 calc R U . . .
C12 C 0.56949(17) 0.75861(11) 0.71366(10) 0.0172(2) Uani 1 1 d . . . . .
C13 C 0.79779(17) 0.69019(12) 0.75881(10) 0.0213(3) Uani 1 1 d . . . . .
H13A H 0.822790 0.592248 0.768000 0.026 Uiso 1 1 calc R U . . .
H13B H 0.893827 0.728969 0.697354 0.026 Uiso 1 1 calc R U . . .
C14 C 0.84184(18) 0.71162(12) 0.88290(10) 0.0228(3) Uani 1 1 d . . . . .
H14 H 0.990028 0.667055 0.910880 0.027 Uiso 1 1 calc R U . . .
C15 C 0.80585(19) 0.86335(12) 0.86793(11) 0.0260(3) Uani 1 1 d . . . . .
H15A H 0.835550 0.877679 0.947343 0.031 Uiso 1 1 calc R U . . .
H15B H 0.901329 0.903581 0.806932 0.031 Uiso 1 1 calc R U . . .
C16 C 0.57890(19) 0.93171(11) 0.82490(10) 0.0234(3) Uani 1 1 d . . . . .
H16 H 0.555317 1.030614 0.815400 0.028 Uiso 1 1 calc R U . . .
C17 C 0.43237(19) 0.86944(12) 0.92106(10) 0.0238(3) Uani 1 1 d . . . . .
H17A H 0.460063 0.883554 1.000863 0.029 Uiso 1 1 calc R U . . .
H17B H 0.285352 0.914017 0.894507 0.029 Uiso 1 1 calc R U . . .
C18 C 0.46837(18) 0.71767(11) 0.93569(10) 0.0210(3) Uani 1 1 d . . . . .
H18 H 0.372786 0.677155 0.998001 0.025 Uiso 1 1 calc R U . . .
C19 C 0.42381(17) 0.69695(11) 0.81205(10) 0.0193(2) Uani 1 1 d . . . . .
H19A H 0.276570 0.740146 0.784991 0.023 Uiso 1 1 calc R U . . .
H19B H 0.444905 0.599127 0.821582 0.023 Uiso 1 1 calc R U . . .
C20 C 0.53465(18) 0.91087(11) 0.70072(10) 0.0210(2) Uani 1 1 d . . . . .
H20A H 0.628414 0.951678 0.638833 0.025 Uiso 1 1 calc R U . . .
H20B H 0.388771 0.956388 0.672112 0.025 Uiso 1 1 calc R U . . .
C21 C 0.69562(19) 0.64928(12) 0.97847(10) 0.0229(3) Uani 1 1 d . . . . .
H21A H 0.724696 0.661768 1.058780 0.027 Uiso 1 1 calc R U . . .
H21B H 0.719572 0.551151 0.988804 0.027 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
N1 C2 1.3698(14) . ?
N1 C10 1.3228(14) . ?
C2 C3 1.4156(15) . ?
C2 C7 1.4228(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3707(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.4129(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3691(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.4193(15) . ?
C7 C8 1.4214(15) . ?
C8 C9 1.3725(15) . ?
C8 C11 1.5028(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.4162(15) . ?
C10 C12 1.5245(14) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.5452(15) . ?
C12 C19 1.5462(15) . ?
C12 C20 1.5440(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5385(15) . ?
C14 H14 1.0000 . ?
C14 C15 1.5334(17) . ?
C14 C21 1.5328(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5322(16) . ?
C16 H16 1.0000 . ?
C16 C17 1.5378(17) . ?
C16 C20 1.5369(15) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5345(16) . ?
C18 H18 1.0000 . ?
C18 C19 1.5310(14) . ?
C18 C21 1.5333(16) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?

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
C10 N1 C2 118.13(9) . . ?
N1 C2 C3 117.99(10) . . ?
N1 C2 C7 122.94(10) . . ?
C3 C2 C7 119.07(10) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.51(10) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.62(11) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.06(10) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.80(10) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C2 118.92(10) . . ?
C6 C7 C8 123.23(10) . . ?
C8 C7 C2 117.85(10) . . ?
C7 C8 C11 121.45(10) . . ?
C9 C8 C7 117.63(10) . . ?
C9 C8 C11 120.92(10) . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.27(10) . . ?
C10 C9 H9 119.4 . . ?
N1 C10 C9 122.18(10) . . ?
N1 C10 C12 115.89(9) . . ?
C9 C10 C12 121.90(10) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 C13 113.58(9) . . ?
C10 C12 C19 108.34(8) . . ?
C10 C12 C20 109.39(9) . . ?
C13 C12 C19 108.32(9) . . ?
C20 C12 C13 108.50(9) . . ?
C20 C12 C19 108.60(9) . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 C12 110.25(9) . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C13 C14 H14 109.4 . . ?
C15 C14 C13 109.47(9) . . ?
C15 C14 H14 109.4 . . ?
C21 C14 C13 109.51(9) . . ?
C21 C14 H14 109.4 . . ?
C21 C14 C15 109.69(10) . . ?
C14 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 C14 109.41(9) . . ?
C16 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C15 C16 H16 109.4 . . ?
C15 C16 C17 109.27(9) . . ?
C15 C16 C20 109.55(10) . . ?
C17 C16 H16 109.4 . . ?
C20 C16 H16 109.4 . . ?
C20 C16 C17 109.79(9) . . ?
C16 C17 H17A 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 C16 109.45(9) . . ?
C18 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
C17 C18 H18 109.5 . . ?
C19 C18 C17 109.38(9) . . ?
C19 C18 H18 109.5 . . ?
C19 C18 C21 109.55(9) . . ?
C21 C18 C17 109.38(9) . . ?
C21 C18 H18 109.5 . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
C18 C19 C12 110.72(9) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C12 C20 H20A 109.6 . . ?
C12 C20 H20B 109.6 . . ?
C16 C20 C12 110.17(9) . . ?
C16 C20 H20A 109.6 . . ?
C16 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C14 C21 C18 109.42(9) . . ?
C14 C21 H21A 109.8 . . ?
C14 C21 H21B 109.8 . . ?
C18 C21 H21A 109.8 . . ?
C18 C21 H21B 109.8 . . ?
H21A C21 H21B 108.2 . . ?

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
N1 C2 C3 C4 -179.38(10) . . . . ?
N1 C2 C7 C6 179.70(9) . . . . ?
N1 C2 C7 C8 -0.19(16) . . . . ?
N1 C10 C12 C13 -178.75(9) . . . . ?
N1 C10 C12 C19 60.85(12) . . . . ?
N1 C10 C12 C20 -57.38(12) . . . . ?
C2 N1 C10 C9 0.15(15) . . . . ?
C2 N1 C10 C12 -178.04(8) . . . . ?
C2 C3 C4 C5 -0.76(17) . . . . ?
C2 C7 C8 C9 -0.35(15) . . . . ?
C2 C7 C8 C11 178.86(10) . . . . ?
C3 C2 C7 C6 0.66(15) . . . . ?
C3 C2 C7 C8 -179.24(9) . . . . ?
C3 C4 C5 C6 1.45(18) . . . . ?
C4 C5 C6 C7 -1.07(17) . . . . ?
C5 C6 C7 C2 0.03(16) . . . . ?
C5 C6 C7 C8 179.91(10) . . . . ?
C6 C7 C8 C9 179.77(10) . . . . ?
C6 C7 C8 C11 -1.03(17) . . . . ?
C7 C2 C3 C4 -0.29(16) . . . . ?
C7 C8 C9 C10 0.78(16) . . . . ?
C8 C9 C10 N1 -0.71(17) . . . . ?
C8 C9 C10 C12 177.38(9) . . . . ?
C9 C10 C12 C13 3.05(15) . . . . ?
C9 C10 C12 C19 -117.35(11) . . . . ?
C9 C10 C12 C20 124.42(11) . . . . ?
C10 N1 C2 C3 179.34(9) . . . . ?
C10 N1 C2 C7 0.29(15) . . . . ?
C10 C12 C13 C14 -179.12(8) . . . . ?
C10 C12 C19 C18 -177.66(8) . . . . ?
C10 C12 C20 C16 176.53(9) . . . . ?
C11 C8 C9 C10 -178.43(10) . . . . ?
C12 C13 C14 C15 -60.03(12) . . . . ?
C12 C13 C14 C21 60.26(12) . . . . ?
C13 C12 C19 C18 58.72(11) . . . . ?
C13 C12 C20 C16 -59.08(12) . . . . ?
C13 C14 C15 C16 60.08(12) . . . . ?
C13 C14 C21 C18 -60.19(12) . . . . ?
C14 C15 C16 C17 60.06(12) . . . . ?
C14 C15 C16 C20 -60.25(12) . . . . ?
C15 C14 C21 C18 59.96(12) . . . . ?
C15 C16 C17 C18 -60.26(11) . . . . ?
C15 C16 C20 C12 60.28(12) . . . . ?
C16 C17 C18 C19 -59.80(12) . . . . ?
C16 C17 C18 C21 60.19(11) . . . . ?
C17 C16 C20 C12 -59.72(12) . . . . ?
C17 C18 C19 C12 60.01(12) . . . . ?
C17 C18 C21 C14 -59.94(11) . . . . ?
C19 C12 C13 C14 -58.71(11) . . . . ?
C19 C12 C20 C16 58.46(12) . . . . ?
C19 C18 C21 C14 59.94(12) . . . . ?
C20 C12 C13 C14 59.01(12) . . . . ?
C20 C12 C19 C18 -58.93(11) . . . . ?
C20 C16 C17 C18 59.91(12) . . . . ?
C21 C14 C15 C16 -60.09(12) . . . . ?
C21 C18 C19 C12 -59.87(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
####################################################################### 
# 
# 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_8v00415_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2179279'
loop_
_audit_author_name
_audit_author_address
'Georgina Rosair'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_audit_creation_date             2022-06-09
_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 H12 N2 O2 S, 0.5(C4 H8 O)'
_chemical_formula_sum            'C20 H16 N2 O2.50 S'
_chemical_formula_weight         356.41
_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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.47480(10)
_cell_length_b                   14.5894(2)
_cell_length_c                   15.1674(2)
_cell_angle_alpha                91.5980(10)
_cell_angle_beta                 101.6100(10)
_cell_angle_gamma                96.6260(10)
_cell_volume                     1607.16(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      74.597
_cell_measurement_theta_min      2.978
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.538
_exptl_absorpt_coefficient_mu    1.962
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0998 before and 0.0528 after correction.
The Ratio of minimum to maximum transmission is 0.8194.
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    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            53419
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.611
_diffrn_reflns_theta_min         2.978
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8Venture'
_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
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5988
_reflns_number_total             6586
_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 V8.40A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.756
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         6586
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.8609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0924
_refine_special_details          'disordered thf and OH groups'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O3-C5S \\sim O1S-C5S \\sim O1S-C2S \\sim O3-C2S
 with sigma of 0.02
 C3T-C3S \\sim C5S-C3T \\sim C5S-C2T \\sim C5S-C4S \\sim C4S-C3S \\sim C3S-C2S
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O1T) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(O1S) = Uanis(O3)
Uanis(C3T) = Uanis(C2S)
4. Others
 Sof(H3SC)=Sof(H3SD)=Sof(H5SC)=Sof(H5SD)=Sof(C2T)=Sof(H2TA)=Sof(H2TB)=Sof(C3T)=
 Sof(H3TA)=Sof(H3TB)=1-FVAR(1)
 Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(H3SA)=Sof(H3SB)=Sof(C4S)=Sof(H4SA)=Sof(H4SB)=
 Sof(H5SA)=Sof(H5SB)=FVAR(1)
 Sof(O1T)=0.7*(1-FVAR(3))
 Sof(O3)=0.3*(1-FVAR(3))
 Sof(O1S)=FVAR(2)
 Sof(H2B)=Sof(H1B)=1-FVAR(3)
 Sof(H1A)=Sof(H2A)=FVAR(3)
 Sof(H2'A)=Sof(H1'A)=1-FVAR(4)
 Sof(H1')=Sof(H2')=FVAR(4)
5.a Secondary CH2 refined with riding coordinates:
 C2S(H2SA,H2SB), C3S(H3SA,H3SB), C3S(H3SC,H3SD), C4S(H4SA,H4SB), C5S(H5SC,
 H5SD), C5S(H5SA,H5SB), C2T(H2TA,H2TB), C3T(H3TA,H3TB)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C4'(H4'), C5'(H5'), C8'(H8'), C9'(H9'), C11'(H11'),
 C12'(H12'), C13'(H13'), C14'(H14'), C16'(H16'), C17'(H17')
5.c Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O2(H2A), O1'(H1'), O2'(H2')
;
_atom_sites_solution_hydrogens   mixed
_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 1.35630(5) 0.34928(2) 1.08678(2) 0.01749(9) Uani 1 1 d . . . . .
O1 O 0.84411(16) 0.15698(8) 0.57717(7) 0.0245(2) Uani 1 1 d . . . . .
H1A H 0.858830 0.211847 0.562037 0.037 Uiso 0.48(3) 1 calc R U P A 1
O2 O 1.71788(17) -0.00513(8) 1.47027(7) 0.0269(3) Uani 1 1 d . . . . .
H2A H 1.759515 0.042711 1.503542 0.040 Uiso 0.48(3) 1 calc R U P A 1
N1 N 1.25592(16) 0.29438(7) 0.99286(7) 0.0153(2) Uani 1 1 d . . . . .
N2 N 1.42254(16) 0.26574(8) 1.14770(7) 0.0156(2) Uani 1 1 d . . . . .
C2 C 1.36511(17) 0.18736(9) 1.09540(8) 0.0128(2) Uani 1 1 d . . . . .
C3 C 1.27047(17) 0.20403(9) 1.00553(8) 0.0128(2) Uani 1 1 d . . . . .
C4 C 1.39118(17) 0.09545(9) 1.12257(9) 0.0136(2) Uani 1 1 d . . . . .
C5 C 1.3215(2) 0.02693(9) 1.05663(9) 0.0185(3) Uani 1 1 d . . . . .
H5 H 1.335011 -0.035149 1.071213 0.022 Uiso 1 1 calc R U . . .
C6 C 1.20014(18) 0.12957(9) 0.93941(9) 0.0140(3) Uani 1 1 d . . . . .
C7 C 1.10227(18) 0.14094(9) 0.84621(9) 0.0136(2) Uani 1 1 d . . . . .
C8 C 0.96700(18) 0.07088(9) 0.80194(9) 0.0163(3) Uani 1 1 d . . . . .
H8 H 0.934196 0.018513 0.833800 0.020 Uiso 1 1 calc R U . . .
C9 C 0.88014(18) 0.07630(9) 0.71281(9) 0.0172(3) Uani 1 1 d . . . . .
H9 H 0.788103 0.028323 0.684304 0.021 Uiso 1 1 calc R U . . .
C10 C 0.92810(18) 0.15213(9) 0.66530(9) 0.0159(3) Uani 1 1 d . . . . .
C11 C 1.06085(18) 0.22302(9) 0.70791(9) 0.0155(3) Uani 1 1 d . . . . .
H11 H 1.092952 0.275200 0.675646 0.019 Uiso 1 1 calc R U . . .
C12 C 1.14630(18) 0.21756(9) 0.79739(9) 0.0143(3) Uani 1 1 d . . . . .
H12 H 1.236001 0.266484 0.826013 0.017 Uiso 1 1 calc R U . . .
C13 C 1.56722(18) -0.00797(9) 1.22569(9) 0.0159(3) Uani 1 1 d . . . . .
H13 H 1.571783 -0.045422 1.174130 0.019 Uiso 1 1 calc R U . . .
C14 C 1.64563(19) -0.03445(9) 1.31043(9) 0.0168(3) Uani 1 1 d . . . . .
H14 H 1.704021 -0.089076 1.316660 0.020 Uiso 1 1 calc R U . . .
C15 C 1.63813(19) 0.01947(9) 1.38601(9) 0.0165(3) Uani 1 1 d . . . . .
C16 C 1.55226(18) 0.09939(9) 1.37673(9) 0.0156(3) Uani 1 1 d . . . . .
H16 H 1.545678 0.135695 1.428693 0.019 Uiso 1 1 calc R U . . .
C17 C 1.47609(17) 0.12609(9) 1.29141(9) 0.0140(2) Uani 1 1 d . . . . .
H17 H 1.419741 0.181352 1.285552 0.017 Uiso 1 1 calc R U . . .
C18 C 1.2311(2) 0.04320(9) 0.96850(9) 0.0185(3) Uani 1 1 d . . . . .
H18 H 1.189260 -0.008397 0.926886 0.022 Uiso 1 1 calc R U . . .
C00D C 1.48124(17) 0.07273(9) 1.21404(9) 0.0133(2) Uani 1 1 d . . . . .
C1 C 0.33616(18) 0.66479(9) 0.11387(9) 0.0151(3) Uani 1 1 d . . . . .
S1' S 0.09052(4) 0.45671(2) -0.12824(2) 0.01533(9) Uani 1 1 d . . . . .
O1' O -0.28221(16) 0.80437(8) -0.51284(7) 0.0261(2) Uani 1 1 d . . . . .
H1' H -0.318862 0.756116 -0.546130 0.039 Uiso 0.49(3) 1 calc R U P B 1
O2' O 0.60550(16) 0.64201(8) 0.38041(7) 0.0238(2) Uani 1 1 d . . . . .
H2' H 0.613925 0.586267 0.390895 0.036 Uiso 0.49(3) 1 calc R U P B 1
N1' N 0.03049(15) 0.54081(7) -0.18970(7) 0.0153(2) Uani 1 1 d . . . . .
N2' N 0.19011(15) 0.51197(7) -0.03438(7) 0.0143(2) Uani 1 1 d . . . . .
C1' C 0.08500(17) 0.61924(9) -0.13735(9) 0.0139(3) Uani 1 1 d . . . . .
C2' C 0.17815(17) 0.60258(9) -0.04709(9) 0.0132(2) Uani 1 1 d . . . . .
C3' C 0.24517(18) 0.67693(9) 0.01951(9) 0.0158(3) Uani 1 1 d . . . . .
C4' C 0.2145(2) 0.76331(10) -0.00981(10) 0.0232(3) Uani 1 1 d . . . . .
H4' H 0.257686 0.815058 0.031490 0.028 Uiso 1 1 calc R U . . .
C5' C 0.1225(2) 0.77936(9) -0.09794(10) 0.0227(3) Uani 1 1 d . . . . .
H5' H 0.104574 0.841126 -0.111984 0.027 Uiso 1 1 calc R U . . .
C6' C 0.05747(18) 0.71085(9) -0.16441(9) 0.0162(3) Uani 1 1 d . . . . .
C7' C -0.03201(18) 0.73293(9) -0.25630(9) 0.0151(3) Uani 1 1 d . . . . .
C8' C 0.02096(18) 0.81827(9) -0.29039(9) 0.0165(3) Uani 1 1 d . . . . .
H8' H 0.115691 0.860322 -0.254290 0.020 Uiso 1 1 calc R U . . .
C9' C -0.06146(18) 0.84255(9) -0.37521(9) 0.0166(3) Uani 1 1 d . . . . .
H9' H -0.023940 0.900670 -0.396811 0.020 Uiso 1 1 calc R U . . .
C10' C -0.19937(19) 0.78124(9) -0.42841(9) 0.0167(3) Uani 1 1 d . . . . .
C11' C -0.25488(19) 0.69650(9) -0.39642(9) 0.0170(3) Uani 1 1 d . . . . .
H11' H -0.349814 0.654843 -0.432869 0.020 Uiso 1 1 calc R U . . .
C12' C -0.17181(18) 0.67270(9) -0.31133(9) 0.0155(3) Uani 1 1 d . . . . .
H12' H -0.210466 0.614577 -0.290092 0.019 Uiso 1 1 calc R U . . .
C13' C 0.32095(19) 0.72763(9) 0.18278(9) 0.0179(3) Uani 1 1 d . . . . .
H13' H 0.248217 0.776538 0.168460 0.021 Uiso 1 1 calc R U . . .
C14' C 0.4093(2) 0.72012(10) 0.27116(9) 0.0198(3) Uani 1 1 d . . . . .
H14' H 0.398267 0.763999 0.316608 0.024 Uiso 1 1 calc R U . . .
C15' C 0.51439(19) 0.64826(9) 0.29335(9) 0.0174(3) Uani 1 1 d . . . . .
C16' C 0.52864(18) 0.58365(9) 0.22681(9) 0.0162(3) Uani 1 1 d . . . . .
H16' H 0.597742 0.533545 0.241940 0.019 Uiso 1 1 calc R U . . .
C17' C 0.44126(18) 0.59266(9) 0.13795(9) 0.0155(3) Uani 1 1 d . . . . .
H17' H 0.453268 0.548837 0.092643 0.019 Uiso 1 1 calc R U . . .
O1S O 0.8931(4) 0.3271(2) 0.51499(19) 0.0281(7) Uani 0.400(4) 1 d D . P C 1
C2S C 0.8664(5) 0.3992(2) 0.5750(2) 0.0297(6) Uani 0.549(3) 1 d D . P C 1
H2SA H 0.986900 0.432779 0.605004 0.036 Uiso 0.549(3) 1 calc R U P C 1
H2SB H 0.804701 0.372395 0.621974 0.036 Uiso 0.549(3) 1 calc R U P C 1
C3S C 0.7487(2) 0.46554(11) 0.52206(11) 0.0292(3) Uani 1 1 d D . . . .
H3SA H 0.626807 0.461713 0.538794 0.035 Uiso 0.549(3) 1 calc R U P C 1
H3SB H 0.809519 0.529902 0.534071 0.035 Uiso 0.549(3) 1 calc R U P C 1
H3SC H 0.644908 0.458786 0.553857 0.035 Uiso 0.451(3) 1 calc R U P C 2
H3SD H 0.834391 0.520729 0.548661 0.035 Uiso 0.451(3) 1 calc R U P C 2
C4S C 0.7284(5) 0.4356(3) 0.4236(2) 0.0284(8) Uani 0.549(3) 1 d D . P C 1
H4SA H 0.821273 0.470930 0.395417 0.034 Uiso 0.549(3) 1 calc R U P C 1
H4SB H 0.603382 0.440400 0.388342 0.034 Uiso 0.549(3) 1 calc R U P C 1
C5S C 0.7661(3) 0.32981(13) 0.43647(13) 0.0410(4) Uani 1 1 d D . . . .
H5SC H 0.856756 0.292845 0.418096 0.049 Uiso 0.451(3) 1 calc R U P C 2
H5SD H 0.653353 0.287792 0.438710 0.049 Uiso 0.451(3) 1 calc R U P C 2
H5SA H 0.650405 0.290621 0.439560 0.049 Uiso 0.549(3) 1 calc R U P C 1
H5SB H 0.813560 0.306352 0.384891 0.049 Uiso 0.549(3) 1 calc R U P C 1
O1T O 0.6809(4) 0.47545(19) 0.42618(18) 0.0173(6) Uani 0.420(3) 1 d . U P C 2
C2T C 0.7258(5) 0.3961(2) 0.3766(3) 0.0193(7) Uani 0.451(3) 1 d D . P C 2
H2TA H 0.619796 0.371951 0.327999 0.023 Uiso 0.451(3) 1 calc R U P C 2
H2TB H 0.832689 0.414919 0.348945 0.023 Uiso 0.451(3) 1 calc R U P C 2
C3T C 0.8476(6) 0.3799(3) 0.5312(3) 0.0297(6) Uani 0.451(3) 1 d D . P C 2
H3TA H 0.816783 0.342265 0.580595 0.036 Uiso 0.451(3) 1 calc R U P C 2
H3TB H 0.982716 0.395847 0.540941 0.036 Uiso 0.451(3) 1 calc R U P C 2
O3 O 0.7864(10) 0.3148(5) 0.5177(4) 0.0281(7) Uani 0.1800(11) 1 d D . P C 3
H2B H 1.716(5) -0.058(3) 1.473(3) 0.029(11) Uiso 0.52(3) 1 d . . P A 2
H1B H 0.805(5) 0.106(3) 0.560(2) 0.024(10) Uiso 0.52(3) 1 d . . P A 2
H2'A H 0.628(5) 0.695(3) 0.403(3) 0.032(12) Uiso 0.51(3) 1 d . . P B 2
H1'A H -0.276(5) 0.858(3) -0.515(2) 0.025(11) Uiso 0.51(3) 1 d . . P B 2


_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 1.6129(11) . ?
S1 N2 1.6131(11) . ?
O1 H1A 0.8400 . ?
O1 C10 1.3653(16) . ?
O1 H1B 0.78(4) . ?
O2 H2A 0.8400 . ?
O2 C15 1.3733(16) . ?
O2 H2B 0.77(4) . ?
N1 C3 1.3510(16) . ?
N2 C2 1.3491(17) . ?
C2 C3 1.4450(17) . ?
C2 C4 1.4369(17) . ?
C3 C6 1.4343(18) . ?
C4 C5 1.3730(19) . ?
C4 C00D 1.4796(17) . ?
C5 H5 0.9500 . ?
C5 C18 1.4111(18) . ?
C6 C7 1.4784(17) . ?
C6 C18 1.3760(18) . ?
C7 C8 1.4028(18) . ?
C7 C12 1.4020(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3856(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3887(19) . ?
C10 C11 1.3926(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.3876(18) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.3862(18) . ?
C13 C00D 1.4038(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3862(19) . ?
C15 C16 1.3917(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3904(18) . ?
C17 H17 0.9500 . ?
C17 C00D 1.3997(18) . ?
C18 H18 0.9500 . ?
C1 C3' 1.4807(17) . ?
C1 C13' 1.4016(19) . ?
C1 C17' 1.3981(18) . ?
S1' N1' 1.6120(11) . ?
S1' N2' 1.6129(11) . ?
O1' H1' 0.8400 . ?
O1' C10' 1.3750(16) . ?
O1' H1'A 0.77(4) . ?
O2' H2' 0.8400 . ?
O2' C15' 1.3692(16) . ?
O2' H2'A 0.83(4) . ?
N1' C1' 1.3480(17) . ?
N2' C2' 1.3517(16) . ?
C1' C2' 1.4463(17) . ?
C1' C6' 1.4344(18) . ?
C2' C3' 1.4346(18) . ?
C3' C4' 1.3767(19) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.4139(19) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.3733(19) . ?
C6' C7' 1.4809(17) . ?
C7' C8' 1.4068(18) . ?
C7' C12' 1.3990(18) . ?
C8' H8' 0.9500 . ?
C8' C9' 1.3846(18) . ?
C9' H9' 0.9500 . ?
C9' C10' 1.3878(19) . ?
C10' C11' 1.3900(19) . ?
C11' H11' 0.9500 . ?
C11' C12' 1.3870(18) . ?
C12' H12' 0.9500 . ?
C13' H13' 0.9500 . ?
C13' C14' 1.3834(19) . ?
C14' H14' 0.9500 . ?
C14' C15' 1.3901(19) . ?
C15' C16' 1.3900(19) . ?
C16' H16' 0.9500 . ?
C16' C17' 1.3914(18) . ?
C17' H17' 0.9500 . ?
O1S C2S 1.428(4) . ?
O1S C5S 1.370(3) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C2S C3S 1.520(4) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C3S H3SC 0.9900 . ?
C3S H3SD 0.9900 . ?
C3S C4S 1.516(4) . ?
C3S O1T 1.458(3) . ?
C3S C3T 1.519(4) . ?
C4S H4SA 0.9900 . ?
C4S H4SB 0.9900 . ?
C4S C5S 1.611(5) . ?
C5S H5SC 0.9900 . ?
C5S H5SD 0.9900 . ?
C5S H5SA 0.9900 . ?
C5S H5SB 0.9900 . ?
C5S C2T 1.363(4) . ?
C5S C3T 1.567(5) . ?
C5S O3 1.240(6) . ?
O1T C2T 1.471(4) . ?
C2T H2TA 0.9900 . ?
C2T H2TB 0.9900 . ?
C3T H3TA 0.9900 . ?
C3T H3TB 0.9900 . ?

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 101.47(6) . . ?
C10 O1 H1A 109.5 . . ?
C10 O1 H1B 106(3) . . ?
C15 O2 H2A 109.5 . . ?
C15 O2 H2B 112(3) . . ?
C3 N1 S1 106.22(9) . . ?
C2 N2 S1 106.41(9) . . ?
N2 C2 C3 112.84(11) . . ?
N2 C2 C4 125.75(12) . . ?
C4 C2 C3 121.41(11) . . ?
N1 C3 C2 113.04(11) . . ?
N1 C3 C6 125.57(12) . . ?
C6 C3 C2 121.39(11) . . ?
C2 C4 C00D 124.51(11) . . ?
C5 C4 C2 114.73(12) . . ?
C5 C4 C00D 120.75(12) . . ?
C4 C5 H5 118.0 . . ?
C4 C5 C18 123.91(12) . . ?
C18 C5 H5 118.0 . . ?
C3 C6 C7 124.63(11) . . ?
C18 C6 C3 114.83(12) . . ?
C18 C6 C7 120.54(12) . . ?
C8 C7 C6 119.74(12) . . ?
C12 C7 C6 122.43(11) . . ?
C12 C7 C8 117.73(12) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.52(12) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.76(12) . . ?
C10 C9 H9 120.1 . . ?
O1 C10 C9 119.78(12) . . ?
O1 C10 C11 120.36(12) . . ?
C9 C10 C11 119.86(12) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.12(12) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 120.99(12) . . ?
C11 C12 H12 119.5 . . ?
C14 C13 H13 119.1 . . ?
C14 C13 C00D 121.74(12) . . ?
C00D C13 H13 119.1 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.44(12) . . ?
C15 C14 H14 120.3 . . ?
O2 C15 C14 120.05(12) . . ?
O2 C15 C16 119.76(12) . . ?
C14 C15 C16 120.18(12) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.00(12) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C00D 120.94(12) . . ?
C00D C17 H17 119.5 . . ?
C5 C18 H18 118.1 . . ?
C6 C18 C5 123.71(12) . . ?
C6 C18 H18 118.1 . . ?
C13 C00D C4 119.66(11) . . ?
C17 C00D C4 122.56(11) . . ?
C17 C00D C13 117.68(12) . . ?
C13' C1 C3' 120.08(12) . . ?
C17' C1 C3' 122.42(12) . . ?
C17' C1 C13' 117.50(12) . . ?
N1' S1' N2' 100.97(6) . . ?
C10' O1' H1' 109.5 . . ?
C10' O1' H1'A 110(3) . . ?
C15' O2' H2' 109.5 . . ?
C15' O2' H2'A 106(3) . . ?
C1' N1' S1' 106.94(9) . . ?
C2' N2' S1' 106.69(9) . . ?
N1' C1' C2' 112.63(11) . . ?
N1' C1' C6' 125.91(12) . . ?
C6' C1' C2' 121.46(11) . . ?
N2' C2' C1' 112.76(11) . . ?
N2' C2' C3' 125.84(12) . . ?
C3' C2' C1' 121.39(11) . . ?
C2' C3' C1 124.35(12) . . ?
C4' C3' C1 120.84(12) . . ?
C4' C3' C2' 114.80(12) . . ?
C3' C4' H4' 118.2 . . ?
C3' C4' C5' 123.70(13) . . ?
C5' C4' H4' 118.2 . . ?
C4' C5' H5' 118.1 . . ?
C6' C5' C4' 123.82(13) . . ?
C6' C5' H5' 118.1 . . ?
C1' C6' C7' 124.19(12) . . ?
C5' C6' C1' 114.81(12) . . ?
C5' C6' C7' 121.00(12) . . ?
C8' C7' C6' 119.72(12) . . ?
C12' C7' C6' 122.67(12) . . ?
C12' C7' C8' 117.60(12) . . ?
C7' C8' H8' 119.2 . . ?
C9' C8' C7' 121.68(12) . . ?
C9' C8' H8' 119.2 . . ?
C8' C9' H9' 120.3 . . ?
C8' C9' C10' 119.42(12) . . ?
C10' C9' H9' 120.3 . . ?
O1' C10' C9' 120.04(12) . . ?
O1' C10' C11' 119.78(12) . . ?
C9' C10' C11' 120.18(12) . . ?
C10' C11' H11' 120.0 . . ?
C12' C11' C10' 120.08(12) . . ?
C12' C11' H11' 120.0 . . ?
C7' C12' H12' 119.5 . . ?
C11' C12' C7' 121.04(12) . . ?
C11' C12' H12' 119.5 . . ?
C1 C13' H13' 119.2 . . ?
C14' C13' C1 121.56(12) . . ?
C14' C13' H13' 119.2 . . ?
C13' C14' H14' 120.1 . . ?
C13' C14' C15' 119.90(13) . . ?
C15' C14' H14' 120.1 . . ?
O2' C15' C14' 119.95(12) . . ?
O2' C15' C16' 120.18(12) . . ?
C16' C15' C14' 119.86(12) . . ?
C15' C16' H16' 120.1 . . ?
C15' C16' C17' 119.72(12) . . ?
C17' C16' H16' 120.1 . . ?
C1 C17' H17' 119.3 . . ?
C16' C17' C1 121.44(12) . . ?
C16' C17' H17' 119.3 . . ?
C5S O1S C2S 107.1(3) . . ?
O1S C2S H2SA 109.8 . . ?
O1S C2S H2SB 109.8 . . ?
O1S C2S C3S 109.4(3) . . ?
H2SA C2S H2SB 108.2 . . ?
C3S C2S H2SA 109.8 . . ?
C3S C2S H2SB 109.8 . . ?
C2S C3S H3SA 110.6 . . ?
C2S C3S H3SB 110.6 . . ?
H3SA C3S H3SB 108.7 . . ?
H3SC C3S H3SD 108.5 . . ?
C4S C3S C2S 105.7(2) . . ?
C4S C3S H3SA 110.6 . . ?
C4S C3S H3SB 110.6 . . ?
O1T C3S H3SC 110.2 . . ?
O1T C3S H3SD 110.2 . . ?
O1T C3S C3T 107.4(2) . . ?
C3T C3S H3SC 110.2 . . ?
C3T C3S H3SD 110.2 . . ?
C3S C4S H4SA 112.1 . . ?
C3S C4S H4SB 112.1 . . ?
C3S C4S C5S 98.4(2) . . ?
H4SA C4S H4SB 109.7 . . ?
C5S C4S H4SA 112.1 . . ?
C5S C4S H4SB 112.1 . . ?
O1S C5S C4S 107.8(2) . . ?
O1S C5S H5SA 110.1 . . ?
O1S C5S H5SB 110.1 . . ?
C4S C5S H5SA 110.1 . . ?
C4S C5S H5SB 110.1 . . ?
H5SC C5S H5SD 108.5 . . ?
H5SA C5S H5SB 108.5 . . ?
C2T C5S H5SC 110.2 . . ?
C2T C5S H5SD 110.2 . . ?
C2T C5S C3T 107.6(3) . . ?
C3T C5S H5SC 110.2 . . ?
C3T C5S H5SD 110.2 . . ?
C3S O1T C2T 108.0(2) . . ?
C5S C2T O1T 107.6(3) . . ?
C5S C2T H2TA 110.2 . . ?
C5S C2T H2TB 110.2 . . ?
O1T C2T H2TA 110.2 . . ?
O1T C2T H2TB 110.2 . . ?
H2TA C2T H2TB 108.5 . . ?
C3S C3T C5S 100.2(3) . . ?
C3S C3T H3TA 111.7 . . ?
C3S C3T H3TB 111.7 . . ?
C5S C3T H3TA 111.7 . . ?
C5S C3T H3TB 111.7 . . ?
H3TA C3T H3TB 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C3 C2 0.65(13) . . . . ?
S1 N1 C3 C6 179.99(11) . . . . ?
S1 N2 C2 C3 1.06(13) . . . . ?
S1 N2 C2 C4 -178.87(11) . . . . ?
O1 C10 C11 C12 -179.74(12) . . . . ?
O2 C15 C16 C17 178.09(12) . . . . ?
N1 S1 N2 C2 -0.62(10) . . . . ?
N1 C3 C6 C7 0.8(2) . . . . ?
N1 C3 C6 C18 -179.62(13) . . . . ?
N2 S1 N1 C3 -0.03(10) . . . . ?
N2 C2 C3 N1 -1.16(16) . . . . ?
N2 C2 C3 C6 179.47(12) . . . . ?
N2 C2 C4 C5 -179.38(13) . . . . ?
N2 C2 C4 C00D 2.0(2) . . . . ?
C2 C3 C6 C7 -179.89(11) . . . . ?
C2 C3 C6 C18 -0.33(18) . . . . ?
C2 C4 C5 C18 0.1(2) . . . . ?
C2 C4 C00D C13 -153.89(13) . . . . ?
C2 C4 C00D C17 29.75(19) . . . . ?
C3 C2 C4 C5 0.69(18) . . . . ?
C3 C2 C4 C00D -177.97(11) . . . . ?
C3 C6 C7 C8 -149.24(13) . . . . ?
C3 C6 C7 C12 34.46(19) . . . . ?
C3 C6 C18 C5 1.2(2) . . . . ?
C4 C2 C3 N1 178.77(12) . . . . ?
C4 C2 C3 C6 -0.60(19) . . . . ?
C4 C5 C18 C6 -1.1(2) . . . . ?
C5 C4 C00D C13 27.52(19) . . . . ?
C5 C4 C00D C17 -148.84(13) . . . . ?
C6 C7 C8 C9 -176.00(12) . . . . ?
C6 C7 C12 C11 175.37(12) . . . . ?
C7 C6 C18 C5 -179.25(13) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C8 C7 C12 C11 -1.01(19) . . . . ?
C8 C9 C10 O1 179.22(12) . . . . ?
C8 C9 C10 C11 -1.1(2) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C10 C11 C12 C7 0.49(19) . . . . ?
C12 C7 C8 C9 0.48(19) . . . . ?
C13 C14 C15 O2 -178.93(13) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C14 C13 C00D C4 -176.85(12) . . . . ?
C14 C13 C00D C17 -0.3(2) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C15 C16 C17 C00D 1.2(2) . . . . ?
C16 C17 C00D C4 175.88(12) . . . . ?
C16 C17 C00D C13 -0.55(19) . . . . ?
C18 C6 C7 C8 31.22(19) . . . . ?
C18 C6 C7 C12 -145.08(13) . . . . ?
C00D C4 C5 C18 178.83(13) . . . . ?
C00D C13 C14 C15 0.5(2) . . . . ?
C1 C3' C4' C5' -177.58(14) . . . . ?
C1 C13' C14' C15' -0.8(2) . . . . ?
S1' N1' C1' C2' 0.79(13) . . . . ?
S1' N1' C1' C6' -179.18(11) . . . . ?
S1' N2' C2' C1' -0.47(13) . . . . ?
S1' N2' C2' C3' 178.54(11) . . . . ?
O1' C10' C11' C12' 179.96(12) . . . . ?
O2' C15' C16' C17' -177.54(12) . . . . ?
N1' S1' N2' C2' 0.85(10) . . . . ?
N1' C1' C2' N2' -0.22(16) . . . . ?
N1' C1' C2' C3' -179.27(12) . . . . ?
N1' C1' C6' C5' 178.68(13) . . . . ?
N1' C1' C6' C7' -1.8(2) . . . . ?
N2' S1' N1' C1' -0.97(10) . . . . ?
N2' C2' C3' C1 -1.0(2) . . . . ?
N2' C2' C3' C4' -179.32(13) . . . . ?
C1' C2' C3' C1 177.91(12) . . . . ?
C1' C2' C3' C4' -0.40(19) . . . . ?
C1' C6' C7' C8' -149.28(13) . . . . ?
C1' C6' C7' C12' 32.0(2) . . . . ?
C2' C1' C6' C5' -1.29(19) . . . . ?
C2' C1' C6' C7' 178.23(12) . . . . ?
C2' C3' C4' C5' 0.8(2) . . . . ?
C3' C1 C13' C14' -177.77(13) . . . . ?
C3' C1 C17' C16' 178.68(12) . . . . ?
C3' C4' C5' C6' -1.6(3) . . . . ?
C4' C5' C6' C1' 1.7(2) . . . . ?
C4' C5' C6' C7' -177.83(14) . . . . ?
C5' C6' C7' C8' 30.2(2) . . . . ?
C5' C6' C7' C12' -148.51(14) . . . . ?
C6' C1' C2' N2' 179.75(12) . . . . ?
C6' C1' C2' C3' 0.70(19) . . . . ?
C6' C7' C8' C9' -178.72(12) . . . . ?
C6' C7' C12' C11' 178.75(12) . . . . ?
C7' C8' C9' C10' -0.3(2) . . . . ?
C8' C7' C12' C11' 0.01(19) . . . . ?
C8' C9' C10' O1' -179.89(12) . . . . ?
C8' C9' C10' C11' 0.4(2) . . . . ?
C9' C10' C11' C12' -0.4(2) . . . . ?
C10' C11' C12' C7' 0.1(2) . . . . ?
C12' C7' C8' C9' 0.06(19) . . . . ?
C13' C1 C3' C2' -150.19(13) . . . . ?
C13' C1 C3' C4' 28.0(2) . . . . ?
C13' C1 C17' C16' -0.39(19) . . . . ?
C13' C14' C15' O2' 178.45(13) . . . . ?
C13' C14' C15' C16' -0.7(2) . . . . ?
C14' C15' C16' C17' 1.6(2) . . . . ?
C15' C16' C17' C1 -1.1(2) . . . . ?
C17' C1 C3' C2' 30.8(2) . . . . ?
C17' C1 C3' C4' -151.02(14) . . . . ?
C17' C1 C13' C14' 1.3(2) . . . . ?
O1S C2S C3S C4S -7.6(3) . . . . ?
C2S O1S C5S C4S 31.3(3) . . . . ?
C2S C3S C4S C5S 23.2(2) . . . . ?
C3S C4S C5S O1S -34.3(3) . . . . ?
C3S O1T C2T C5S 16.8(3) . . . . ?
C5S O1S C2S C3S -15.3(3) . . . . ?
O1T C3S C3T C5S -18.7(3) . . . . ?
C2T C5S C3T C3S 29.8(3) . . . . ?
C3T C3S O1T C2T 3.1(3) . . . . ?
C3T C5S C2T O1T -29.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Grown by slow evaporation of THF.'
####################################################################### 
# 
# 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_8v00385_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2179274'
loop_
_audit_author_name
_audit_author_address
'Georgina Rosair'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_audit_creation_date             2022-06-09
_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         'C30 H20 N2 S'
_chemical_formula_sum            'C30 H20 N2 S'
_chemical_formula_weight         440.54
_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                   16.0078(3)
_cell_length_b                   7.33120(10)
_cell_length_c                   17.9268(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.6553(6)
_cell_angle_gamma                90
_cell_volume                     2103.69(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9604
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      74.371
_cell_measurement_theta_min      3.681
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.553
_exptl_absorpt_coefficient_mu    1.526
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1500 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.7572.
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    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            74879
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.480
_diffrn_reflns_theta_min         3.681
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8Venture'
_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                4119
_reflns_number_total             4284
_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 V8.40A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 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         0.286
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.048
_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)+(0.0477P)²+0.9707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0852
_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:
 C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C24(H24), C26(H26),
  C27(H27), C28(H28), C29(H29), C30(H30)
;
_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 0.35976(2) 0.39574(4) 0.44940(2) 0.01576(9) Uani 1 1 d . . . . .
N1 N 0.28379(6) 0.44098(13) 0.39258(5) 0.0149(2) Uani 1 1 d . . . . .
N2 N 0.43901(6) 0.46058(13) 0.40161(5) 0.0149(2) Uani 1 1 d . . . . .
C1 C 0.31851(7) 0.51191(15) 0.33069(6) 0.0128(2) Uani 1 1 d . . . . .
C2 C 0.40851(7) 0.52266(15) 0.33577(6) 0.0131(2) Uani 1 1 d . . . . .
C3 C 0.45718(7) 0.58954(15) 0.27505(6) 0.0130(2) Uani 1 1 d . . . . .
C4 C 0.41251(7) 0.63686(15) 0.21203(6) 0.0141(2) Uani 1 1 d . . . . .
H4 H 0.442300 0.678934 0.169850 0.017 Uiso 1 1 calc R U . . .
C5 C 0.32435(7) 0.62602(15) 0.20684(6) 0.0138(2) Uani 1 1 d . . . . .
H5 H 0.298094 0.660483 0.161182 0.017 Uiso 1 1 calc R U . . .
C6 C 0.27455(7) 0.56825(15) 0.26434(6) 0.0129(2) Uani 1 1 d . . . . .
C7 C 0.18228(7) 0.57040(15) 0.25677(6) 0.0130(2) Uani 1 1 d . . . . .
C8 C 0.14514(7) 0.53635(15) 0.18691(6) 0.0149(2) Uani 1 1 d . . . . .
H8 H 0.179239 0.508062 0.145453 0.018 Uiso 1 1 calc R U . . .
C9 C 0.05903(7) 0.54364(16) 0.17784(6) 0.0162(2) Uani 1 1 d . . . . .
H9 H 0.034682 0.522255 0.130066 0.019 Uiso 1 1 calc R U . . .
C10 C 0.00809(7) 0.58200(15) 0.23815(6) 0.0155(2) Uani 1 1 d . . . . .
H10 H -0.050823 0.586737 0.231401 0.019 Uiso 1 1 calc R U . . .
C11 C 0.04330(7) 0.61363(14) 0.30870(6) 0.0139(2) Uani 1 1 d . . . . .
C12 C 0.13046(7) 0.60901(14) 0.31698(6) 0.0136(2) Uani 1 1 d . . . . .
H12 H 0.154842 0.632641 0.364570 0.016 Uiso 1 1 calc R U . . .
C13 C -0.01010(7) 0.64260(15) 0.37513(6) 0.0142(2) Uani 1 1 d . . . . .
C14 C -0.08674(7) 0.55155(16) 0.38119(6) 0.0166(2) Uani 1 1 d . . . . .
H14 H -0.107064 0.480399 0.340586 0.020 Uiso 1 1 calc R U . . .
C15 C -0.13341(7) 0.56424(17) 0.44609(7) 0.0183(2) Uani 1 1 d . . . . .
H15 H -0.185180 0.501621 0.449498 0.022 Uiso 1 1 calc R U . . .
C16 C -0.10457(7) 0.66801(16) 0.50579(6) 0.0179(2) Uani 1 1 d . . . . .
H16 H -0.135698 0.674283 0.550513 0.022 Uiso 1 1 calc R U . . .
C17 C -0.02971(7) 0.76271(16) 0.49957(6) 0.0179(2) Uani 1 1 d . . . . .
H17 H -0.010319 0.836207 0.539836 0.021 Uiso 1 1 calc R U . . .
C18 C 0.01700(7) 0.75056(16) 0.43476(6) 0.0162(2) Uani 1 1 d . . . . .
H18 H 0.067882 0.816468 0.431080 0.019 Uiso 1 1 calc R U . . .
C19 C 0.54864(7) 0.61709(15) 0.27995(6) 0.0134(2) Uani 1 1 d . . . . .
C20 C 0.58762(7) 0.67033(16) 0.34669(6) 0.0152(2) Uani 1 1 d . . . . .
H20 H 0.556095 0.679780 0.391100 0.018 Uiso 1 1 calc R U . . .
C21 C 0.67240(7) 0.70930(16) 0.34789(6) 0.0170(2) Uani 1 1 d . . . . .
H21 H 0.698731 0.744093 0.393472 0.020 Uiso 1 1 calc R U . . .
C22 C 0.71941(7) 0.69814(16) 0.28331(6) 0.0159(2) Uani 1 1 d . . . . .
H22 H 0.777406 0.725420 0.285262 0.019 Uiso 1 1 calc R U . . .
C23 C 0.68212(7) 0.64713(15) 0.21546(6) 0.0135(2) Uani 1 1 d . . . . .
C24 C 0.59696(7) 0.60417(15) 0.21539(6) 0.0135(2) Uani 1 1 d . . . . .
H24 H 0.571065 0.565035 0.170210 0.016 Uiso 1 1 calc R U . . .
C25 C 0.73100(7) 0.64387(15) 0.14502(6) 0.0137(2) Uani 1 1 d . . . . .
C26 C 0.80832(7) 0.73293(16) 0.14093(6) 0.0156(2) Uani 1 1 d . . . . .
H26 H 0.829378 0.796042 0.183438 0.019 Uiso 1 1 calc R U . . .
C27 C 0.85482(7) 0.73067(16) 0.07583(6) 0.0185(2) Uani 1 1 d . . . . .
H27 H 0.907631 0.789626 0.074554 0.022 Uiso 1 1 calc R U . . .
C28 C 0.82408(7) 0.64229(17) 0.01271(7) 0.0201(2) Uani 1 1 d . . . . .
H28 H 0.855453 0.641287 -0.031949 0.024 Uiso 1 1 calc R U . . .
C29 C 0.74710(7) 0.55544(17) 0.01547(7) 0.0199(2) Uani 1 1 d . . . . .
H29 H 0.725517 0.495798 -0.027673 0.024 Uiso 1 1 calc R U . . .
C30 C 0.70134(7) 0.55517(16) 0.08102(6) 0.0168(2) Uani 1 1 d . . . . .
H30 H 0.649122 0.493720 0.082269 0.020 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 1.6119(10) . ?
S1 N2 1.6107(9) . ?
N1 C1 1.3507(14) . ?
N2 C2 1.3512(14) . ?
C1 C2 1.4447(14) . ?
C1 C6 1.4357(15) . ?
C2 C3 1.4323(15) . ?
C3 C4 1.3745(15) . ?
C3 C19 1.4796(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.4156(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3771(15) . ?
C6 C7 1.4817(15) . ?
C7 C8 1.4027(15) . ?
C7 C12 1.3978(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.3871(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3904(16) . ?
C10 H10 0.9500 . ?
C10 C11 1.3982(16) . ?
C11 C12 1.4018(15) . ?
C11 C13 1.4891(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.4019(16) . ?
C13 C18 1.3953(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.3929(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3877(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.3905(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.3917(15) . ?
C18 H18 0.9500 . ?
C19 C20 1.3986(15) . ?
C19 C24 1.4026(15) . ?
C20 H20 0.9500 . ?
C20 C21 1.3869(16) . ?
C21 H21 0.9500 . ?
C21 C22 1.3903(15) . ?
C22 H22 0.9500 . ?
C22 C23 1.3996(15) . ?
C23 C24 1.3991(15) . ?
C23 C25 1.4933(15) . ?
C24 H24 0.9500 . ?
C25 C26 1.4021(15) . ?
C25 C30 1.3972(16) . ?
C26 H26 0.9500 . ?
C26 C27 1.3914(15) . ?
C27 H27 0.9500 . ?
C27 C28 1.3891(17) . ?
C28 H28 0.9500 . ?
C28 C29 1.3885(17) . ?
C29 H29 0.9500 . ?
C29 C30 1.3919(16) . ?
C30 H30 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 101.32(5) . . ?
C1 N1 S1 106.49(7) . . ?
C2 N2 S1 106.57(7) . . ?
N1 C1 C2 112.87(9) . . ?
N1 C1 C6 126.08(10) . . ?
C6 C1 C2 121.03(10) . . ?
N2 C2 C1 112.75(9) . . ?
N2 C2 C3 125.80(10) . . ?
C3 C2 C1 121.43(10) . . ?
C2 C3 C19 123.23(10) . . ?
C4 C3 C2 115.38(10) . . ?
C4 C3 C19 121.29(10) . . ?
C3 C4 H4 118.4 . . ?
C3 C4 C5 123.28(10) . . ?
C5 C4 H4 118.4 . . ?
C4 C5 H5 118.2 . . ?
C6 C5 C4 123.60(10) . . ?
C6 C5 H5 118.2 . . ?
C1 C6 C7 123.89(10) . . ?
C5 C6 C1 115.22(10) . . ?
C5 C6 C7 120.87(10) . . ?
C8 C7 C6 119.46(10) . . ?
C12 C7 C6 122.09(10) . . ?
C12 C7 C8 118.44(10) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.55(10) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.51(10) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.19(10) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 118.83(10) . . ?
C10 C11 C13 121.19(10) . . ?
C12 C11 C13 119.90(10) . . ?
C7 C12 C11 121.46(10) . . ?
C7 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C11 120.33(10) . . ?
C18 C13 C11 121.15(10) . . ?
C18 C13 C14 118.39(10) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.74(11) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.25(11) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.43(10) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.44(11) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.71(10) . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C3 121.36(10) . . ?
C20 C19 C24 118.68(10) . . ?
C24 C19 C3 119.77(10) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.85(10) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 120.92(10) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.66(10) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C25 121.12(10) . . ?
C24 C23 C22 117.82(10) . . ?
C24 C23 C25 121.03(10) . . ?
C19 C24 H24 119.0 . . ?
C23 C24 C19 122.05(10) . . ?
C23 C24 H24 119.0 . . ?
C26 C25 C23 120.54(10) . . ?
C30 C25 C23 121.70(10) . . ?
C30 C25 C26 117.76(10) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 C25 121.29(10) . . ?
C27 C26 H26 119.4 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 120.06(11) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 120.3 . . ?
C29 C28 C27 119.42(11) . . ?
C29 C28 H28 120.3 . . ?
C28 C29 H29 119.8 . . ?
C28 C29 C30 120.43(11) . . ?
C30 C29 H29 119.8 . . ?
C25 C30 H30 119.5 . . ?
C29 C30 C25 121.03(11) . . ?
C29 C30 H30 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 C2 0.16(11) . . . . ?
S1 N1 C1 C6 178.43(9) . . . . ?
S1 N2 C2 C1 0.45(11) . . . . ?
S1 N2 C2 C3 -178.22(9) . . . . ?
N1 S1 N2 C2 -0.33(8) . . . . ?
N1 C1 C2 N2 -0.42(14) . . . . ?
N1 C1 C2 C3 178.32(10) . . . . ?
N1 C1 C6 C5 -176.15(11) . . . . ?
N1 C1 C6 C7 5.32(18) . . . . ?
N2 S1 N1 C1 0.10(9) . . . . ?
N2 C2 C3 C4 176.82(10) . . . . ?
N2 C2 C3 C19 -6.60(17) . . . . ?
C1 C2 C3 C4 -1.75(15) . . . . ?
C1 C2 C3 C19 174.83(10) . . . . ?
C1 C6 C7 C8 -148.01(11) . . . . ?
C1 C6 C7 C12 33.27(16) . . . . ?
C2 C1 C6 C5 1.98(15) . . . . ?
C2 C1 C6 C7 -176.55(10) . . . . ?
C2 C3 C4 C5 1.61(16) . . . . ?
C2 C3 C19 C20 -33.07(16) . . . . ?
C2 C3 C19 C24 152.11(11) . . . . ?
C3 C4 C5 C6 0.41(18) . . . . ?
C3 C19 C20 C21 -174.77(10) . . . . ?
C3 C19 C24 C23 173.35(10) . . . . ?
C4 C3 C19 C20 143.31(11) . . . . ?
C4 C3 C19 C24 -31.50(15) . . . . ?
C4 C5 C6 C1 -2.21(16) . . . . ?
C4 C5 C6 C7 176.37(10) . . . . ?
C5 C6 C7 C8 33.54(16) . . . . ?
C5 C6 C7 C12 -145.18(11) . . . . ?
C6 C1 C2 N2 -178.78(10) . . . . ?
C6 C1 C2 C3 -0.04(16) . . . . ?
C6 C7 C8 C9 -177.83(10) . . . . ?
C6 C7 C12 C11 178.89(10) . . . . ?
C7 C8 C9 C10 -1.02(17) . . . . ?
C8 C7 C12 C11 0.17(16) . . . . ?
C8 C9 C10 C11 -0.02(17) . . . . ?
C9 C10 C11 C12 1.09(16) . . . . ?
C9 C10 C11 C13 -175.84(10) . . . . ?
C10 C11 C12 C7 -1.17(16) . . . . ?
C10 C11 C13 C14 33.67(16) . . . . ?
C10 C11 C13 C18 -150.61(11) . . . . ?
C11 C13 C14 C15 173.92(10) . . . . ?
C11 C13 C18 C17 -173.78(10) . . . . ?
C12 C7 C8 C9 0.93(16) . . . . ?
C12 C11 C13 C14 -143.22(11) . . . . ?
C12 C11 C13 C18 32.50(15) . . . . ?
C13 C11 C12 C7 175.80(10) . . . . ?
C13 C14 C15 C16 0.14(17) . . . . ?
C14 C13 C18 C17 2.02(16) . . . . ?
C14 C15 C16 C17 1.56(17) . . . . ?
C15 C16 C17 C18 -1.45(17) . . . . ?
C16 C17 C18 C13 -0.36(17) . . . . ?
C18 C13 C14 C15 -1.92(17) . . . . ?
C19 C3 C4 C5 -175.04(10) . . . . ?
C19 C20 C21 C22 0.70(17) . . . . ?
C20 C19 C24 C23 -1.60(16) . . . . ?
C20 C21 C22 C23 -0.03(18) . . . . ?
C21 C22 C23 C24 -1.40(17) . . . . ?
C21 C22 C23 C25 176.85(10) . . . . ?
C22 C23 C24 C19 2.24(16) . . . . ?
C22 C23 C25 C26 -15.77(16) . . . . ?
C22 C23 C25 C30 165.11(11) . . . . ?
C23 C25 C26 C27 179.75(10) . . . . ?
C23 C25 C30 C29 179.12(11) . . . . ?
C24 C19 C20 C21 0.10(16) . . . . ?
C24 C23 C25 C26 162.43(11) . . . . ?
C24 C23 C25 C30 -16.69(16) . . . . ?
C25 C23 C24 C19 -176.02(10) . . . . ?
C25 C26 C27 C28 1.37(18) . . . . ?
C26 C25 C30 C29 -0.02(17) . . . . ?
C26 C27 C28 C29 -0.49(18) . . . . ?
C27 C28 C29 C30 -0.61(19) . . . . ?
C28 C29 C30 C25 0.88(19) . . . . ?
C30 C25 C26 C27 -1.10(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
