# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_av_av140f4b
_database_code_depnum_ccdc_archive 'CCDC 2363583'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2024-06-18 deposited with the CCDC.	2024-09-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H15 N S'
_chemical_formula_sum            'C25 H15 N S'
_chemical_formula_weight         361.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0985(9)
_cell_length_b                   10.3014(12)
_cell_length_c                   11.0803(12)
_cell_angle_alpha                96.301(4)
_cell_angle_beta                 101.547(3)
_cell_angle_gamma                101.238(4)
_cell_volume                     877.60(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9870
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      32.45

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.193
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6634
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'

#==============================================================================

# EXPERIMENTAL DATA


_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36309
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.563
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5119
_reflns_number_gt                3778
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0330P)²+1.0990P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5119
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.63272(6) 0.87344(5) 0.34413(4) 0.02200(12) Uani 1 1 d . . . . .
N1 N 0.5532(2) 0.51633(16) 0.77104(15) 0.0217(3) Uani 1 1 d . . . . .
C1 C 0.8233(2) 0.84981(19) 0.42999(17) 0.0216(4) Uani 1 1 d . . . . .
H1 H 0.9335 0.8848 0.4148 0.026 Uiso 1 1 calc R U . . .
C2 C 0.7998(2) 0.77603(18) 0.52171(17) 0.0194(4) Uani 1 1 d . . . . .
H2 H 0.8916 0.7539 0.5777 0.023 Uiso 1 1 calc R U . . .
C3 C 0.6213(2) 0.73490(17) 0.52509(16) 0.0158(3) Uani 1 1 d . . . . .
C4 C 0.5420(2) 0.65134(17) 0.60338(16) 0.0156(3) Uani 1 1 d . . . . .
C5 C 0.6320(2) 0.60019(17) 0.70582(17) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.3789(2) 0.48178(19) 0.74117(18) 0.0224(4) Uani 1 1 d . . . . .
H6 H 0.3226 0.4210 0.7865 0.027 Uiso 1 1 calc R U . . .
C7 C 0.2792(2) 0.52932(18) 0.64954(17) 0.0198(4) Uani 1 1 d . . . . .
H7 H 0.1567 0.5044 0.6343 0.024 Uiso 1 1 calc R U . . .
C8 C 0.3591(2) 0.61559(17) 0.57763(16) 0.0160(3) Uani 1 1 d . . . . .
C9 C 0.2576(2) 0.66650(18) 0.48152(16) 0.0176(3) Uani 1 1 d . . . . .
H9 H 0.1352 0.6422 0.4677 0.021 Uiso 1 1 calc R U . . .
C10 C 0.3297(2) 0.74893(17) 0.40850(16) 0.0166(3) Uani 1 1 d . . . . .
C11 C 0.5138(2) 0.78142(17) 0.43213(16) 0.0167(3) Uani 1 1 d . . . . .
C12 C 0.8156(2) 0.63955(18) 0.75171(17) 0.0200(4) Uani 1 1 d . . . . .
C13 C 0.9665(2) 0.67520(18) 0.80126(17) 0.0197(4) Uani 1 1 d . . . . .
C14 C 1.1469(2) 0.71876(18) 0.85851(17) 0.0188(3) Uani 1 1 d . . . . .
C15 C 1.2505(2) 0.82183(19) 0.81768(18) 0.0235(4) Uani 1 1 d . . . . .
H15 H 1.2012 0.8641 0.7519 0.028 Uiso 1 1 calc R U . . .
C16 C 1.4246(3) 0.8624(2) 0.8728(2) 0.0304(5) Uani 1 1 d . . . . .
H16 H 1.4951 0.9322 0.8444 0.036 Uiso 1 1 calc R U . . .
C17 C 1.4967(3) 0.8016(2) 0.9692(2) 0.0342(5) Uani 1 1 d . . . . .
H17 H 1.6166 0.8300 1.0068 0.041 Uiso 1 1 calc R U . . .
C18 C 1.3957(3) 0.7001(2) 1.01106(19) 0.0294(4) Uani 1 1 d . . . . .
H18 H 1.4460 0.6593 1.0777 0.035 Uiso 1 1 calc R U . . .
C19 C 1.2215(2) 0.65766(19) 0.95606(17) 0.0219(4) Uani 1 1 d . . . . .
H19 H 1.1523 0.5871 0.9844 0.026 Uiso 1 1 calc R U . . .
C20 C 0.2187(2) 0.79916(18) 0.30927(16) 0.0170(3) Uani 1 1 d . . . . .
C21 C 0.0770(2) 0.71098(19) 0.22798(17) 0.0196(4) Uani 1 1 d . . . . .
H21 H 0.0551 0.6183 0.2344 0.023 Uiso 1 1 calc R U . . .
C22 C -0.0320(2) 0.7578(2) 0.13808(17) 0.0224(4) Uani 1 1 d . . . . .
H22 H -0.1279 0.6971 0.0833 0.027 Uiso 1 1 calc R U . . .
C23 C -0.0015(2) 0.8926(2) 0.12784(18) 0.0243(4) Uani 1 1 d . . . . .
H23 H -0.0765 0.9245 0.0663 0.029 Uiso 1 1 calc R U . . .
C24 C 0.1392(3) 0.9809(2) 0.20797(19) 0.0247(4) Uani 1 1 d . . . . .
H24 H 0.1605 1.0735 0.2011 0.030 Uiso 1 1 calc R U . . .
C25 C 0.2486(2) 0.93474(19) 0.29795(18) 0.0220(4) Uani 1 1 d . . . . .
H25 H 0.3445 0.9959 0.3523 0.026 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7194(19) . ?
S1 C11 1.7318(17) . ?
N1 C5 1.335(2) . ?
N1 C6 1.349(2) . ?
C1 C2 1.356(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.434(2) . ?
C2 H2 0.9500 . ?
C3 C11 1.400(2) . ?
C3 C4 1.441(2) . ?
C4 C8 1.417(2) . ?
C4 C5 1.431(2) . ?
C5 C12 1.433(2) . ?
C6 C7 1.363(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.407(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.423(2) . ?
C9 C10 1.365(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.427(2) . ?
C10 C20 1.481(2) . ?
C12 C13 1.201(3) . ?
C13 C14 1.431(3) . ?
C14 C15 1.395(3) . ?
C14 C19 1.402(2) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.394(3) . ?
C20 C21 1.398(2) . ?
C21 C22 1.387(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C11 91.56(9) . . ?
C5 N1 C6 117.99(16) . . ?
C2 C1 S1 112.87(14) . . ?
C2 C1 H1 123.6 . . ?
S1 C1 H1 123.6 . . ?
C1 C2 C3 112.75(16) . . ?
C1 C2 H2 123.6 . . ?
C3 C2 H2 123.6 . . ?
C11 C3 C2 111.56(15) . . ?
C11 C3 C4 118.34(15) . . ?
C2 C3 C4 130.03(16) . . ?
C8 C4 C5 116.40(15) . . ?
C8 C4 C3 117.88(15) . . ?
C5 C4 C3 125.72(16) . . ?
N1 C5 C4 123.61(16) . . ?
N1 C5 C12 113.57(16) . . ?
C4 C5 C12 122.76(16) . . ?
N1 C6 C7 123.61(17) . . ?
N1 C6 H6 118.2 . . ?
C7 C6 H6 118.2 . . ?
C6 C7 C8 119.50(17) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C4 118.75(16) . . ?
C7 C8 C9 120.48(16) . . ?
C4 C8 C9 120.77(15) . . ?
C10 C9 C8 122.40(16) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C9 C10 C11 116.68(15) . . ?
C9 C10 C20 120.48(15) . . ?
C11 C10 C20 122.83(15) . . ?
C3 C11 C10 123.85(15) . . ?
C3 C11 S1 111.26(13) . . ?
C10 C11 S1 124.77(13) . . ?
C13 C12 C5 173.7(2) . . ?
C12 C13 C14 179.0(2) . . ?
C15 C14 C19 119.27(17) . . ?
C15 C14 C13 120.51(16) . . ?
C19 C14 C13 120.22(17) . . ?
C16 C15 C14 120.10(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.12(19) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 120.45(19) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.05(19) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 120.01(18) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C25 C20 C21 118.74(17) . . ?
C25 C20 C10 121.21(16) . . ?
C21 C20 C10 120.00(16) . . ?
C22 C21 C20 120.51(17) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 120.30(18) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 119.62(18) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 120.36(18) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C20 120.46(18) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 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
C11 S1 C1 C2 -0.17(16) . . . . ?
S1 C1 C2 C3 0.2(2) . . . . ?
C1 C2 C3 C11 0.0(2) . . . . ?
C1 C2 C3 C4 176.77(18) . . . . ?
C11 C3 C4 C8 3.1(2) . . . . ?
C2 C3 C4 C8 -173.58(17) . . . . ?
C11 C3 C4 C5 -177.09(16) . . . . ?
C2 C3 C4 C5 6.3(3) . . . . ?
C6 N1 C5 C4 -2.4(3) . . . . ?
C6 N1 C5 C12 174.89(16) . . . . ?
C8 C4 C5 N1 4.1(3) . . . . ?
C3 C4 C5 N1 -175.72(17) . . . . ?
C8 C4 C5 C12 -172.88(16) . . . . ?
C3 C4 C5 C12 7.3(3) . . . . ?
C5 N1 C6 C7 -1.0(3) . . . . ?
N1 C6 C7 C8 2.4(3) . . . . ?
C6 C7 C8 C4 -0.4(3) . . . . ?
C6 C7 C8 C9 -179.97(17) . . . . ?
C5 C4 C8 C7 -2.6(2) . . . . ?
C3 C4 C8 C7 177.27(16) . . . . ?
C5 C4 C8 C9 176.98(16) . . . . ?
C3 C4 C8 C9 -3.2(2) . . . . ?
C7 C8 C9 C10 -179.10(17) . . . . ?
C4 C8 C9 C10 1.3(3) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C8 C9 C10 C20 179.82(16) . . . . ?
C2 C3 C11 C10 175.98(16) . . . . ?
C4 C3 C11 C10 -1.2(3) . . . . ?
C2 C3 C11 S1 -0.08(19) . . . . ?
C4 C3 C11 S1 -177.32(13) . . . . ?
C9 C10 C11 C3 -0.6(3) . . . . ?
C20 C10 C11 C3 -179.83(16) . . . . ?
C9 C10 C11 S1 174.93(14) . . . . ?
C20 C10 C11 S1 -4.3(2) . . . . ?
C1 S1 C11 C3 0.14(14) . . . . ?
C1 S1 C11 C10 -175.88(16) . . . . ?
C19 C14 C15 C16 0.2(3) . . . . ?
C13 C14 C15 C16 -179.46(19) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C17 C18 C19 C14 -0.7(3) . . . . ?
C15 C14 C19 C18 0.3(3) . . . . ?
C13 C14 C19 C18 180.00(18) . . . . ?
C9 C10 C20 C25 130.92(19) . . . . ?
C11 C10 C20 C25 -49.9(2) . . . . ?
C9 C10 C20 C21 -46.5(2) . . . . ?
C11 C10 C20 C21 132.71(18) . . . . ?
C25 C20 C21 C22 -0.2(3) . . . . ?
C10 C20 C21 C22 177.30(16) . . . . ?
C20 C21 C22 C23 0.0(3) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C20 0.0(3) . . . . ?
C21 C20 C25 C24 0.2(3) . . . . ?
C10 C20 C25 C24 -177.24(17) . . . . ?

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_is_av140f1
_database_code_depnum_ccdc_archive 'CCDC 2363584'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2024-06-18 deposited with the CCDC.	2024-09-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H15 N S'
_chemical_formula_sum            'C25 H15 N S'
_chemical_formula_weight         361.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.904(6)
_cell_length_b                   10.247(7)
_cell_length_c                   11.533(8)
_cell_angle_alpha                96.72(2)
_cell_angle_beta                 102.06(2)
_cell_angle_gamma                99.58(2)
_cell_volume                     889.5(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2509
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.85

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.191
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6185
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20493
_diffrn_reflns_av_unetI/netI     0.1069
_diffrn_reflns_av_R_equivalents  0.1212
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.039
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4075
_reflns_number_gt                2451
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+0.0317P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4075
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.7438(3) 0.4765(2) 0.3625(2) 0.0225(5) Uani 1 1 d . . . . .
S1 S 0.36828(10) 0.13258(8) 0.64074(7) 0.0242(2) Uani 1 1 d . . . . .
C1 C 0.1735(4) 0.1604(3) 0.5558(2) 0.0238(7) Uani 1 1 d . . . . .
H1 H 0.0605 0.1268 0.5685 0.029 Uiso 1 1 calc R U . . .
C2 C 0.1986(4) 0.2348(3) 0.4695(2) 0.0204(6) Uani 1 1 d . . . . .
H2 H 0.1053 0.2593 0.4153 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3824(4) 0.2734(3) 0.4684(2) 0.0182(6) Uani 1 1 d . . . . .
C4 C 0.4631(4) 0.3561(3) 0.3936(2) 0.0185(6) Uani 1 1 d . . . . .
C5 C 0.3701(4) 0.4001(3) 0.2897(2) 0.0210(6) Uani 1 1 d . . . . .
C6 C 0.4662(4) 0.4820(3) 0.2299(3) 0.0250(7) Uani 1 1 d . . . . .
H6 H 0.4077 0.5135 0.1611 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6503(4) 0.5187(3) 0.2703(3) 0.0264(7) Uani 1 1 d . . . . .
H7 H 0.7119 0.5778 0.2286 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6515(3) 0.3951(3) 0.4234(2) 0.0189(6) Uani 1 1 d . . . . .
C9 C 0.7549(4) 0.3470(3) 0.5201(2) 0.0207(6) Uani 1 1 d . . . . .
H9 H 0.8795 0.3756 0.5392 0.025 Uiso 1 1 calc R U . . .
C10 C 0.6806(3) 0.2609(3) 0.5864(2) 0.0184(6) Uani 1 1 d . . . . .
C11 C 0.4921(4) 0.2258(3) 0.5591(2) 0.0204(6) Uani 1 1 d . . . . .
C12 C 0.1825(4) 0.3578(3) 0.2407(2) 0.0214(6) Uani 1 1 d . . . . .
C13 C 0.0293(4) 0.3209(3) 0.1927(2) 0.0226(6) Uani 1 1 d . . . . .
C14 C -0.1564(4) 0.2701(3) 0.1427(2) 0.0216(6) Uani 1 1 d . . . . .
C15 C -0.2510(4) 0.1803(3) 0.1999(3) 0.0260(7) Uani 1 1 d . . . . .
H15 H -0.1923 0.1536 0.2712 0.031 Uiso 1 1 calc R U . . .
C16 C -0.4287(4) 0.1301(3) 0.1534(3) 0.0356(8) Uani 1 1 d . . . . .
H16 H -0.4919 0.0693 0.1928 0.043 Uiso 1 1 calc R U . . .
C17 C -0.5149(4) 0.1685(3) 0.0495(3) 0.0411(9) Uani 1 1 d . . . . .
H17 H -0.6375 0.1345 0.0181 0.049 Uiso 1 1 calc R U . . .
C18 C -0.4235(4) 0.2559(3) -0.0087(3) 0.0360(8) Uani 1 1 d . . . . .
H18 H -0.4829 0.2804 -0.0809 0.043 Uiso 1 1 calc R U . . .
C19 C -0.2459(4) 0.3079(3) 0.0374(3) 0.0281(7) Uani 1 1 d . . . . .
H19 H -0.1843 0.3695 -0.0023 0.034 Uiso 1 1 calc R U . . .
C20 C 0.7917(3) 0.2076(3) 0.6848(2) 0.0200(6) Uani 1 1 d . . . . .
C21 C 0.9320(4) 0.2931(3) 0.7678(2) 0.0234(7) Uani 1 1 d . . . . .
H21 H 0.9563 0.3858 0.7625 0.028 Uiso 1 1 calc R U . . .
C22 C 1.0357(4) 0.2435(3) 0.8577(3) 0.0276(7) Uani 1 1 d . . . . .
H22 H 1.1307 0.3023 0.9140 0.033 Uiso 1 1 calc R U . . .
C23 C 1.0013(4) 0.1079(3) 0.8658(3) 0.0313(8) Uani 1 1 d . . . . .
H23 H 1.0721 0.0743 0.9282 0.038 Uiso 1 1 calc R U . . .
C24 C 0.8646(4) 0.0217(3) 0.7835(3) 0.0289(7) Uani 1 1 d . . . . .
H24 H 0.8425 -0.0713 0.7885 0.035 Uiso 1 1 calc R U . . .
C25 C 0.7595(4) 0.0712(3) 0.6933(3) 0.0247(7) Uani 1 1 d . . . . .
H25 H 0.6651 0.0118 0.6370 0.030 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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 C7 1.322(4) . ?
N1 C8 1.367(3) . ?
S1 C1 1.730(3) . ?
S1 C11 1.744(3) . ?
C1 C2 1.349(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.444(4) . ?
C2 H2 0.9500 . ?
C3 C11 1.401(4) . ?
C3 C4 1.446(4) . ?
C4 C5 1.431(4) . ?
C4 C8 1.432(4) . ?
C5 C6 1.378(4) . ?
C5 C12 1.444(4) . ?
C6 C7 1.404(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.427(4) . ?
C9 C10 1.372(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.431(4) . ?
C10 C20 1.498(4) . ?
C12 C13 1.198(4) . ?
C13 C14 1.442(4) . ?
C14 C15 1.399(4) . ?
C14 C19 1.403(4) . ?
C15 C16 1.381(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.396(4) . ?
C20 C25 1.397(4) . ?
C21 C22 1.383(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(4) . ?
C24 H24 0.9500 . ?
C25 H25 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
C7 N1 C8 116.7(2) . . ?
C1 S1 C11 91.40(14) . . ?
C2 C1 S1 113.1(2) . . ?
C2 C1 H1 123.5 . . ?
S1 C1 H1 123.5 . . ?
C1 C2 C3 112.8(3) . . ?
C1 C2 H2 123.6 . . ?
C3 C2 H2 123.6 . . ?
C11 C3 C2 111.8(2) . . ?
C11 C3 C4 118.5(2) . . ?
C2 C3 C4 129.6(3) . . ?
C5 C4 C8 116.8(2) . . ?
C5 C4 C3 125.2(2) . . ?
C8 C4 C3 117.9(2) . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 C12 118.2(3) . . ?
C4 C5 C12 123.5(2) . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
N1 C7 C6 124.4(3) . . ?
N1 C7 H7 117.8 . . ?
C6 C7 H7 117.8 . . ?
N1 C8 C9 115.8(2) . . ?
N1 C8 C4 123.8(2) . . ?
C9 C8 C4 120.4(2) . . ?
C10 C9 C8 122.3(3) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C11 117.1(2) . . ?
C9 C10 C20 121.5(2) . . ?
C11 C10 C20 121.3(2) . . ?
C3 C11 C10 123.5(2) . . ?
C3 C11 S1 111.0(2) . . ?
C10 C11 S1 125.3(2) . . ?
C13 C12 C5 175.7(3) . . ?
C12 C13 C14 175.3(3) . . ?
C15 C14 C19 118.7(3) . . ?
C15 C14 C13 119.6(2) . . ?
C19 C14 C13 121.7(3) . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.1(3) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C21 C20 C25 118.9(3) . . ?
C21 C20 C10 120.5(3) . . ?
C25 C20 C10 120.6(2) . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.1(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.8(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C20 120.5(3) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 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
C11 S1 C1 C2 0.5(2) . . . . ?
S1 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C11 -1.0(3) . . . . ?
C1 C2 C3 C4 -177.6(3) . . . . ?
C11 C3 C4 C5 172.9(3) . . . . ?
C2 C3 C4 C5 -10.7(5) . . . . ?
C11 C3 C4 C8 -5.7(4) . . . . ?
C2 C3 C4 C8 170.7(3) . . . . ?
C8 C4 C5 C6 -3.3(4) . . . . ?
C3 C4 C5 C6 178.2(3) . . . . ?
C8 C4 C5 C12 173.3(3) . . . . ?
C3 C4 C5 C12 -5.3(4) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C12 C5 C6 C7 -176.1(3) . . . . ?
C8 N1 C7 C6 -2.1(4) . . . . ?
C5 C6 C7 N1 2.3(5) . . . . ?
C7 N1 C8 C9 178.0(2) . . . . ?
C7 N1 C8 C4 -0.8(4) . . . . ?
C5 C4 C8 N1 3.5(4) . . . . ?
C3 C4 C8 N1 -177.8(2) . . . . ?
C5 C4 C8 C9 -175.3(2) . . . . ?
C3 C4 C8 C9 3.4(4) . . . . ?
N1 C8 C9 C10 -177.7(3) . . . . ?
C4 C8 C9 C10 1.2(4) . . . . ?
C8 C9 C10 C11 -3.3(4) . . . . ?
C8 C9 C10 C20 177.8(2) . . . . ?
C2 C3 C11 C10 -173.3(2) . . . . ?
C4 C3 C11 C10 3.7(4) . . . . ?
C2 C3 C11 S1 1.3(3) . . . . ?
C4 C3 C11 S1 178.4(2) . . . . ?
C9 C10 C11 C3 0.8(4) . . . . ?
C20 C10 C11 C3 179.7(2) . . . . ?
C9 C10 C11 S1 -173.1(2) . . . . ?
C20 C10 C11 S1 5.9(4) . . . . ?
C1 S1 C11 C3 -1.1(2) . . . . ?
C1 S1 C11 C10 173.5(2) . . . . ?
C19 C14 C15 C16 0.0(4) . . . . ?
C13 C14 C15 C16 -179.8(3) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C18 0.6(5) . . . . ?
C16 C17 C18 C19 -1.2(5) . . . . ?
C17 C18 C19 C14 1.2(5) . . . . ?
C15 C14 C19 C18 -0.6(4) . . . . ?
C13 C14 C19 C18 179.2(3) . . . . ?
C9 C10 C20 C21 45.3(4) . . . . ?
C11 C10 C20 C21 -133.6(3) . . . . ?
C9 C10 C20 C25 -133.1(3) . . . . ?
C11 C10 C20 C25 48.0(4) . . . . ?
C25 C20 C21 C22 -0.8(4) . . . . ?
C10 C20 C21 C22 -179.2(3) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C21 C22 C23 C24 0.7(5) . . . . ?
C22 C23 C24 C25 -1.0(5) . . . . ?
C23 C24 C25 C20 0.3(4) . . . . ?
C21 C20 C25 C24 0.5(4) . . . . ?
C10 C20 C25 C24 178.9(3) . . . . ?

_refine_diff_density_max         0.529
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_is_jp226ph
_database_code_depnum_ccdc_archive 'CCDC 2363585'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2024-06-18 deposited with the CCDC.	2024-09-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H17 N S'
_chemical_formula_sum            'C29 H17 N S'
_chemical_formula_weight         411.49

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'
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'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0321(4)
_cell_length_b                   10.3560(5)
_cell_length_c                   13.1722(6)
_cell_angle_alpha                105.953(2)
_cell_angle_beta                 95.907(2)
_cell_angle_gamma                108.672(2)
_cell_volume                     975.86(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9861
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      31.07

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7108
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'

#==============================================================================

# EXPERIMENTAL DATA


_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53873
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.738
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5693
_reflns_number_gt                4636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0606P)²+0.3554P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5693
_refine_ls_number_parameters     381
_refine_ls_number_restraints     193
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
S1A S 1.01274(4) 0.79779(3) 0.58576(3) 0.02191(10) Uani 0.9648(12) 1 d D U P A
1
C1A C 0.9051(2) 0.7837(2) 0.46232(13) 0.0226(3) Uani 0.9648(12) 1 d D . P A 1
H1A H 0.9339 0.8594 0.4320 0.027 Uiso 0.9648(12) 1 calc R U P A 1
C2A C 0.77160(17) 0.65011(13) 0.41144(10) 0.0186(2) Uani 0.9648(12) 1 d D . P A
1
C3A C 0.64820(17) 0.59052(14) 0.30803(10) 0.0196(2) Uani 0.9648(12) 1 d D . P A
1
C4A C 0.52964(17) 0.45062(14) 0.27720(10) 0.0204(2) Uani 0.9648(12) 1 d D . P A
1
H4A H 0.4498 0.4119 0.2087 0.024 Uiso 0.9648(12) 1 calc R U P A 1
C5A C 0.52015(17) 0.35981(13) 0.34327(10) 0.0190(2) Uani 0.9648(12) 1 d D . P A
1
C6A C 0.40085(17) 0.21359(14) 0.31495(10) 0.0204(2) Uani 0.9648(12) 1 d D . P A
1
C7A C 0.26917(18) 0.14015(14) 0.21691(11) 0.0245(3) Uani 0.9648(12) 1 d D . P A
1
H7A H 0.2578 0.1892 0.1668 0.029 Uiso 0.9648(12) 1 calc R U P A 1
C8A C 0.1585(2) -0.00080(15) 0.19410(12) 0.0279(3) Uani 0.9648(12) 1 d D . P A
1
H8A H 0.0706 -0.0481 0.1287 0.033 Uiso 0.9648(12) 1 calc R U P A 1
C9A C 0.1741(5) -0.0759(2) 0.2667(2) 0.0298(3) Uani 0.9648(12) 1 d D . P A 1
H9A H 0.0976 -0.1738 0.2494 0.036 Uiso 0.9648(12) 1 calc R U P A 1
C10A C 0.2985(2) -0.00909(15) 0.36195(12) 0.0270(3) Uani 0.9648(12) 1 d D . P A
1
H10A H 0.3074 -0.0610 0.4103 0.032 Uiso 0.9648(12) 1 calc R U P A 1
C11A C 0.41500(19) 0.13778(14) 0.38940(11) 0.0218(3) Uani 0.9648(12) 1 d D . P
A 1
N1A N 0.53272(15) 0.19619(12) 0.48663(9) 0.0226(2) Uani 0.9648(12) 1 d D . P A
1
C12A C 0.64235(17) 0.33415(14) 0.51335(10) 0.0196(2) Uani 0.9648(12) 1 d D . P
A 1
C13A C 0.76681(18) 0.40295(14) 0.61602(10) 0.0216(3) Uani 0.9648(12) 1 d D . P
A 1
H13A H 0.7678 0.3484 0.6633 0.026 Uiso 0.9648(12) 1 calc R U P A 1
C14A C 0.88453(17) 0.54395(14) 0.64908(10) 0.0198(2) Uani 0.9648(12) 1 d D . P
A 1
C15A C 0.88591(17) 0.62275(13) 0.57440(10) 0.0186(2) Uani 0.9648(12) 1 d D . P
A 1
C16A C 0.76385(16) 0.55947(13) 0.47614(10) 0.0182(2) Uani 0.9648(12) 1 d D . P
A 1
C17A C 0.64034(16) 0.41685(13) 0.44368(10) 0.0179(2) Uani 0.9648(12) 1 d D . P
A 1
C18A C 0.65079(17) 0.67959(14) 0.23699(10) 0.0206(2) Uani 0.9648(12) 1 d D . P
A 1
C19A C 0.67052(19) 0.63041(16) 0.13062(11) 0.0255(3) Uani 0.9648(12) 1 d D . P
A 1
H19A H 0.6803 0.5387 0.1033 0.031 Uiso 0.9648(12) 1 calc R U P A 1
C20A C 0.6759(2) 0.71523(17) 0.06461(11) 0.0295(3) Uani 0.9648(12) 1 d D . P A
1
H20A H 0.6904 0.6815 -0.0074 0.035 Uiso 0.9648(12) 1 calc R U P A 1
C21A C 0.66045(19) 0.84855(16) 0.10304(11) 0.0285(3) Uani 0.9648(12) 1 d D . P
A 1
H21A H 0.6662 0.9068 0.0580 0.034 Uiso 0.9648(12) 1 calc R U P A 1
C22A C 0.63647(19) 0.89648(16) 0.20782(12) 0.0273(3) Uani 0.9648(12) 1 d D . P
A 1
H22A H 0.6227 0.9868 0.2338 0.033 Uiso 0.9648(12) 1 calc R U P A 1
C23A C 0.63245(19) 0.81350(15) 0.27477(11) 0.0241(3) Uani 0.9648(12) 1 d D . P
A 1
H23A H 0.6172 0.8477 0.3466 0.029 Uiso 0.9648(12) 1 calc R U P A 1
C24A C 0.99911(17) 0.61230(14) 0.75951(10) 0.0212(3) Uani 0.9648(12) 1 d D . P
A 1
C25A C 1.17261(18) 0.71341(15) 0.77952(11) 0.0241(3) Uani 0.9648(12) 1 d D . P
A 1
H25A H 1.2189 0.7391 0.7214 0.029 Uiso 0.9648(12) 1 calc R U P A 1
C26A C 1.27869(19) 0.77712(16) 0.88317(11) 0.0283(3) Uani 0.9648(12) 1 d D . P
A 1
H26A H 1.3974 0.8444 0.8951 0.034 Uiso 0.9648(12) 1 calc R U P A 1
C27A C 1.2122(2) 0.74305(17) 0.96916(11) 0.0308(3) Uani 0.9648(12) 1 d D . P A
1
H27A H 1.2844 0.7870 1.0401 0.037 Uiso 0.9648(12) 1 calc R U P A 1
C28A C 1.0390(2) 0.64396(17) 0.95067(11) 0.0305(3) Uani 0.9648(12) 1 d D . P A
1
H28A H 0.9921 0.6212 1.0095 0.037 Uiso 0.9648(12) 1 calc R U P A 1
C29A C 0.93378(19) 0.57775(16) 0.84682(11) 0.0261(3) Uani 0.9648(12) 1 d D . P
A 1
H29A H 0.8165 0.5084 0.8350 0.031 Uiso 0.9648(12) 1 calc R U P A 1
S1B S 0.9111(18) 0.8235(12) 0.4586(10) 0.023(2) Uiso 0.0352(12) 1 d D U P A 2
C1B C 0.896(5) 0.7661(17) 0.5688(12) 0.028(3) Uiso 0.0352(12) 1 d D U P A 2
H1B H 0.9293 0.8290 0.6414 0.034 Uiso 0.0352(12) 1 calc R U P A 2
C2B C 0.829(4) 0.6168(17) 0.5395(14) 0.021(3) Uiso 0.0352(12) 1 d D U P A 2
C3B C 0.820(4) 0.5179(19) 0.5992(16) 0.031(4) Uiso 0.0352(12) 1 d D U P A 2
C4B C 0.699(4) 0.377(2) 0.5529(18) 0.023(4) Uiso 0.0352(12) 1 d D U P A 2
H4B H 0.6918 0.3117 0.5918 0.028 Uiso 0.0352(12) 1 calc R U P A 2
C5B C 0.585(4) 0.327(2) 0.4473(17) 0.030(3) Uiso 0.0352(12) 1 d D U P A 2
C6B C 0.450(6) 0.187(2) 0.392(2) 0.034(4) Uiso 0.0352(12) 1 d D U P A 2
C7B C 0.421(5) 0.071(2) 0.435(2) 0.035(5) Uiso 0.0352(12) 1 d D U P A 2
H7B H 0.4981 0.0836 0.4994 0.041 Uiso 0.0352(12) 1 calc R U P A 2
C8B C 0.284(5) -0.058(3) 0.382(3) 0.036(5) Uiso 0.0352(12) 1 d D U P A 2
H8B H 0.2590 -0.1314 0.4148 0.044 Uiso 0.0352(12) 1 calc R U P A 2
C9B C 0.179(15) -0.083(7) 0.282(7) 0.034(5) Uiso 0.0352(12) 1 d D U P A 2
H9B H 0.0811 -0.1724 0.2482 0.041 Uiso 0.0352(12) 1 calc R U P A 2
C10B C 0.217(5) 0.018(2) 0.231(2) 0.036(4) Uiso 0.0352(12) 1 d D U P A 2
H10B H 0.1563 -0.0042 0.1590 0.044 Uiso 0.0352(12) 1 calc R U P A 2
C11B C 0.348(5) 0.159(2) 0.287(2) 0.032(4) Uiso 0.0352(12) 1 d D U P A 2
N1B N 0.373(4) 0.2544(19) 0.2317(17) 0.031(4) Uiso 0.0352(12) 1 d D U P A 2
C12B C 0.499(4) 0.385(2) 0.2836(18) 0.027(3) Uiso 0.0352(12) 1 d D U P A 2
C13B C 0.526(4) 0.4870(18) 0.2253(17) 0.026(3) Uiso 0.0352(12) 1 d D U P A 2
H13B H 0.4625 0.4561 0.1528 0.031 Uiso 0.0352(12) 1 calc R U P A 2
C14B C 0.643(3) 0.6277(17) 0.2719(13) 0.017(3) Uiso 0.0352(12) 1 d D U P A 2
C15B C 0.748(4) 0.6619(18) 0.3767(16) 0.024(3) Uiso 0.0352(12) 1 d D U P A 2
C16B C 0.736(4) 0.5621(16) 0.4299(15) 0.026(3) Uiso 0.0352(12) 1 d D U P A 2
C17B C 0.605(4) 0.4213(18) 0.3868(17) 0.026(3) Uiso 0.0352(12) 1 d D U P A 2
C18B C 0.930(3) 0.568(3) 0.7105(13) 0.028(4) Uiso 0.0352(12) 1 d DG U P A 2
C19B C 1.104(3) 0.669(3) 0.7375(17) 0.037(5) Uiso 0.0352(12) 1 d DG U P A 2
H19B H 1.1566 0.7019 0.6835 0.045 Uiso 0.0352(12) 1 calc R U P A 2
C20B C 1.200(3) 0.723(3) 0.8435(19) 0.032(5) Uiso 0.0352(12) 1 d DG U P A 2
H20B H 1.3186 0.7927 0.8619 0.039 Uiso 0.0352(12) 1 calc R U P A 2
C21B C 1.122(4) 0.676(3) 0.9225(14) 0.038(5) Uiso 0.0352(12) 1 d DG U P A 2
H21B H 1.1881 0.7127 0.9950 0.046 Uiso 0.0352(12) 1 calc R U P A 2
C22B C 0.949(4) 0.574(3) 0.8955(15) 0.035(5) Uiso 0.0352(12) 1 d DG U P A 2
H22B H 0.8957 0.5417 0.9495 0.043 Uiso 0.0352(12) 1 calc R U P A 2
C23B C 0.852(3) 0.520(3) 0.7895(17) 0.037(4) Uiso 0.0352(12) 1 d DG U P A 2
H23B H 0.7337 0.4508 0.7710 0.044 Uiso 0.0352(12) 1 calc R U P A 2
C24B C 0.669(3) 0.7293(18) 0.2094(13) 0.023(4) Uiso 0.0352(12) 1 d DG U P A 2
C25B C 0.699(3) 0.6881(19) 0.1054(14) 0.015(4) Uiso 0.0352(12) 1 d DG U P A 2
H25B H 0.7119 0.5979 0.0764 0.018 Uiso 0.0352(12) 1 calc R U P A 2
C26B C 0.710(4) 0.779(2) 0.0436(13) 0.023(4) Uiso 0.0352(12) 1 d DG U P A 2
H26B H 0.7306 0.7505 -0.0275 0.028 Uiso 0.0352(12) 1 calc R U P A 2
C27B C 0.691(4) 0.911(2) 0.0859(17) 0.022(4) Uiso 0.0352(12) 1 d DG U P A 2
H27B H 0.6987 0.9726 0.0437 0.027 Uiso 0.0352(12) 1 calc R U P A 2
C28B C 0.661(4) 0.9519(19) 0.1900(18) 0.025(4) Uiso 0.0352(12) 1 d DG U P A 2
H28B H 0.6481 1.0421 0.2189 0.031 Uiso 0.0352(12) 1 calc R U P A 2
C29B C 0.650(3) 0.861(2) 0.2517(13) 0.017(4) Uiso 0.0352(12) 1 d DG U P A 2
H29B H 0.6294 0.8895 0.3229 0.020 Uiso 0.0352(12) 1 calc R U P A 2


#==============================================================================

# MOLECULAR GEOMETRY

_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
S1A C1A 1.7065(17) . ?
S1A C15A 1.7272(13) . ?
C1A C2A 1.381(2) . ?
C1A H1A 0.9500 . ?
C2A C16A 1.4229(17) . ?
C2A C3A 1.4447(17) . ?
C3A C4A 1.3727(18) . ?
C3A C18A 1.4809(18) . ?
C4A C5A 1.4371(18) . ?
C4A H4A 0.9500 . ?
C5A C17A 1.4045(17) . ?
C5A C6A 1.4273(17) . ?
C6A C7A 1.4243(18) . ?
C6A C11A 1.4313(19) . ?
C7A C8A 1.3725(19) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.408(2) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.369(2) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.4270(19) . ?
C10A H10A 0.9500 . ?
C11A N1A 1.3634(17) . ?
N1A C12A 1.3396(17) . ?
C12A C17A 1.4191(18) . ?
C12A C13A 1.4394(18) . ?
C13A C14A 1.3775(18) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.4392(18) . ?
C14A C24A 1.4850(17) . ?
C15A C16A 1.3882(17) . ?
C16A C17A 1.4056(17) . ?
C18A C19A 1.3974(18) . ?
C18A C23A 1.3997(18) . ?
C19A C20A 1.390(2) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.384(2) . ?
C20A H20A 0.9500 . ?
C21A C22A 1.388(2) . ?
C21A H21A 0.9500 . ?
C22A C23A 1.3864(19) . ?
C22A H22A 0.9500 . ?
C23A H23A 0.9500 . ?
C24A C25A 1.3951(19) . ?
C24A C29A 1.3986(19) . ?
C25A C26A 1.3895(18) . ?
C25A H25A 0.9500 . ?
C26A C27A 1.384(2) . ?
C26A H26A 0.9500 . ?
C27A C28A 1.388(2) . ?
C27A H27A 0.9500 . ?
C28A C29A 1.3898(19) . ?
C28A H28A 0.9500 . ?
C29A H29A 0.9500 . ?
S1B C1B 1.716(10) . ?
S1B C15B 1.730(9) . ?
C1B C2B 1.387(9) . ?
C1B H1B 0.9500 . ?
C2B C16B 1.421(9) . ?
C2B C3B 1.443(9) . ?
C3B C4B 1.383(9) . ?
C3B C18B 1.491(8) . ?
C4B C5B 1.443(9) . ?
C4B H4B 0.9500 . ?
C5B C17B 1.400(9) . ?
C5B C6B 1.436(9) . ?
C6B C7B 1.426(9) . ?
C6B C11B 1.435(9) . ?
C7B C8B 1.369(10) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.407(10) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.368(10) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.431(9) . ?
C10B H10B 0.9500 . ?
C11B N1B 1.357(9) . ?
N1B C12B 1.340(9) . ?
C12B C17B 1.411(9) . ?
C12B C13B 1.443(9) . ?
C13B C14B 1.375(9) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.430(9) . ?
C14B C24B 1.483(8) . ?
C15B C16B 1.384(9) . ?
C16B C17B 1.413(9) . ?
C18B C19B 1.3900 . ?
C18B C23B 1.3900 . ?
C19B C20B 1.3900 . ?
C19B H19B 0.9500 . ?
C20B C21B 1.3900 . ?
C20B H20B 0.9500 . ?
C21B C22B 1.3900 . ?
C21B H21B 0.9500 . ?
C22B C23B 1.3900 . ?
C22B H22B 0.9500 . ?
C23B H23B 0.9500 . ?
C24B C25B 1.3900 . ?
C24B C29B 1.3900 . ?
C25B C26B 1.3900 . ?
C25B H25B 0.9500 . ?
C26B C27B 1.3900 . ?
C26B H26B 0.9500 . ?
C27B C28B 1.3900 . ?
C27B H27B 0.9500 . ?
C28B C29B 1.3900 . ?
C28B H28B 0.9500 . ?
C29B H29B 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
C1A S1A C15A 93.14(8) . . ?
C2A C1A S1A 112.48(13) . . ?
C2A C1A H1A 123.8 . . ?
S1A C1A H1A 123.8 . . ?
C1A C2A C16A 110.42(12) . . ?
C1A C2A C3A 131.76(13) . . ?
C16A C2A C3A 117.81(11) . . ?
C4A C3A C2A 118.85(12) . . ?
C4A C3A C18A 120.96(11) . . ?
C2A C3A C18A 120.19(11) . . ?
C3A C4A C5A 123.31(11) . . ?
C3A C4A H4A 118.3 . . ?
C5A C4A H4A 118.3 . . ?
C17A C5A C6A 116.20(12) . . ?
C17A C5A C4A 118.13(11) . . ?
C6A C5A C4A 125.65(12) . . ?
C7A C6A C5A 123.35(12) . . ?
C7A C6A C11A 118.71(12) . . ?
C5A C6A C11A 117.94(11) . . ?
C8A C7A C6A 120.62(13) . . ?
C8A C7A H7A 119.7 . . ?
C6A C7A H7A 119.7 . . ?
C7A C8A C9A 120.65(14) . . ?
C7A C8A H8A 119.7 . . ?
C9A C8A H8A 119.7 . . ?
C10A C9A C8A 120.54(14) . . ?
C10A C9A H9A 119.7 . . ?
C8A C9A H9A 119.7 . . ?
C9A C10A C11A 120.66(14) . . ?
C9A C10A H10A 119.7 . . ?
C11A C10A H10A 119.7 . . ?
N1A C11A C10A 116.63(12) . . ?
N1A C11A C6A 124.56(12) . . ?
C10A C11A C6A 118.81(12) . . ?
C12A N1A C11A 117.13(11) . . ?
N1A C12A C17A 122.22(12) . . ?
N1A C12A C13A 119.77(12) . . ?
C17A C12A C13A 118.01(11) . . ?
C14A C13A C12A 123.25(12) . . ?
C14A C13A H13A 118.4 . . ?
C12A C13A H13A 118.4 . . ?
C13A C14A C15A 117.45(11) . . ?
C13A C14A C24A 120.61(12) . . ?
C15A C14A C24A 121.89(11) . . ?
C16A C15A C14A 120.08(11) . . ?
C16A C15A S1A 108.86(10) . . ?
C14A C15A S1A 130.98(10) . . ?
C15A C16A C17A 122.36(12) . . ?
C15A C16A C2A 115.08(11) . . ?
C17A C16A C2A 122.55(11) . . ?
C5A C17A C16A 119.35(11) . . ?
C5A C17A C12A 121.93(11) . . ?
C16A C17A C12A 118.72(11) . . ?
C19A C18A C23A 118.96(12) . . ?
C19A C18A C3A 120.29(12) . . ?
C23A C18A C3A 120.75(11) . . ?
C20A C19A C18A 120.20(13) . . ?
C20A C19A H19A 119.9 . . ?
C18A C19A H19A 119.9 . . ?
C21A C20A C19A 120.52(13) . . ?
C21A C20A H20A 119.7 . . ?
C19A C20A H20A 119.7 . . ?
C20A C21A C22A 119.55(13) . . ?
C20A C21A H21A 120.2 . . ?
C22A C21A H21A 120.2 . . ?
C23A C22A C21A 120.49(13) . . ?
C23A C22A H22A 119.8 . . ?
C21A C22A H22A 119.8 . . ?
C22A C23A C18A 120.26(13) . . ?
C22A C23A H23A 119.9 . . ?
C18A C23A H23A 119.9 . . ?
C25A C24A C29A 118.23(12) . . ?
C25A C24A C14A 121.40(12) . . ?
C29A C24A C14A 120.37(12) . . ?
C26A C25A C24A 121.01(13) . . ?
C26A C25A H25A 119.5 . . ?
C24A C25A H25A 119.5 . . ?
C27A C26A C25A 120.30(14) . . ?
C27A C26A H26A 119.8 . . ?
C25A C26A H26A 119.8 . . ?
C26A C27A C28A 119.33(13) . . ?
C26A C27A H27A 120.3 . . ?
C28A C27A H27A 120.3 . . ?
C27A C28A C29A 120.57(14) . . ?
C27A C28A H28A 119.7 . . ?
C29A C28A H28A 119.7 . . ?
C28A C29A C24A 120.55(14) . . ?
C28A C29A H29A 119.7 . . ?
C24A C29A H29A 119.7 . . ?
C1B S1B C15B 91.0(7) . . ?
C2B C1B S1B 111.9(10) . . ?
C2B C1B H1B 124.0 . . ?
S1B C1B H1B 124.0 . . ?
C1B C2B C16B 107.3(9) . . ?
C1B C2B C3B 133.3(11) . . ?
C16B C2B C3B 119.0(9) . . ?
C4B C3B C2B 118.3(10) . . ?
C4B C3B C18B 120.8(10) . . ?
C2B C3B C18B 120.8(11) . . ?
C3B C4B C5B 122.2(11) . . ?
C3B C4B H4B 118.9 . . ?
C5B C4B H4B 118.9 . . ?
C17B C5B C6B 113.3(9) . . ?
C17B C5B C4B 118.9(10) . . ?
C6B C5B C4B 127.8(10) . . ?
C7B C6B C11B 118.5(10) . . ?
C7B C6B C5B 122.1(11) . . ?
C11B C6B C5B 119.3(10) . . ?
C8B C7B C6B 120.0(12) . . ?
C8B C7B H7B 120.0 . . ?
C6B C7B H7B 120.0 . . ?
C7B C8B C9B 121.2(13) . . ?
C7B C8B H8B 119.4 . . ?
C9B C8B H8B 119.4 . . ?
C10B C9B C8B 120.6(14) . . ?
C10B C9B H9B 119.7 . . ?
C8B C9B H9B 119.7 . . ?
C9B C10B C11B 119.8(13) . . ?
C9B C10B H10B 120.1 . . ?
C11B C10B H10B 120.1 . . ?
N1B C11B C10B 115.6(11) . . ?
N1B C11B C6B 125.1(10) . . ?
C10B C11B C6B 119.1(10) . . ?
C12B N1B C11B 115.4(11) . . ?
N1B C12B C17B 123.0(10) . . ?
N1B C12B C13B 115.8(10) . . ?
C17B C12B C13B 121.2(10) . . ?
C14B C13B C12B 121.7(11) . . ?
C14B C13B H13B 119.2 . . ?
C12B C13B H13B 119.2 . . ?
C13B C14B C15B 115.8(10) . . ?
C13B C14B C24B 120.3(10) . . ?
C15B C14B C24B 123.5(11) . . ?
C16B C15B C14B 123.3(9) . . ?
C16B C15B S1B 107.4(7) . . ?
C14B C15B S1B 129.3(9) . . ?
C15B C16B C17B 120.9(10) . . ?
C15B C16B C2B 116.6(9) . . ?
C17B C16B C2B 120.7(11) . . ?
C5B C17B C12B 123.9(9) . . ?
C5B C17B C16B 119.6(9) . . ?
C12B C17B C16B 116.6(9) . . ?
C19B C18B C23B 120.0 . . ?
C19B C18B C3B 120.6(10) . . ?
C23B C18B C3B 119.2(10) . . ?
C18B C19B C20B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C20B C19B H19B 120.0 . . ?
C21B C20B C19B 120.0 . . ?
C21B C20B H20B 120.0 . . ?
C19B C20B H20B 120.0 . . ?
C22B C21B C20B 120.0 . . ?
C22B C21B H21B 120.0 . . ?
C20B C21B H21B 120.0 . . ?
C23B C22B C21B 120.0 . . ?
C23B C22B H22B 120.0 . . ?
C21B C22B H22B 120.0 . . ?
C22B C23B C18B 120.0 . . ?
C22B C23B H23B 120.0 . . ?
C18B C23B H23B 120.0 . . ?
C25B C24B C29B 120.0 . . ?
C25B C24B C14B 119.9(10) . . ?
C29B C24B C14B 120.0(10) . . ?
C26B C25B C24B 120.0 . . ?
C26B C25B H25B 120.0 . . ?
C24B C25B H25B 120.0 . . ?
C25B C26B C27B 120.0 . . ?
C25B C26B H26B 120.0 . . ?
C27B C26B H26B 120.0 . . ?
C28B C27B C26B 120.0 . . ?
C28B C27B H27B 120.0 . . ?
C26B C27B H27B 120.0 . . ?
C27B C28B C29B 120.0 . . ?
C27B C28B H28B 120.0 . . ?
C29B C28B H28B 120.0 . . ?
C28B C29B C24B 120.0 . . ?
C28B C29B H29B 120.0 . . ?
C24B C29B H29B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15A S1A C1A C2A 1.01(13) . . . . ?
S1A C1A C2A C16A -1.28(16) . . . . ?
S1A C1A C2A C3A -179.96(12) . . . . ?
C1A C2A C3A C4A 178.82(15) . . . . ?
C16A C2A C3A C4A 0.22(18) . . . . ?
C1A C2A C3A C18A -1.1(2) . . . . ?
C16A C2A C3A C18A -179.67(11) . . . . ?
C2A C3A C4A C5A 0.69(19) . . . . ?
C18A C3A C4A C5A -179.41(12) . . . . ?
C3A C4A C5A C17A -0.99(19) . . . . ?
C3A C4A C5A C6A -179.45(12) . . . . ?
C17A C5A C6A C7A 179.09(12) . . . . ?
C4A C5A C6A C7A -2.4(2) . . . . ?
C17A C5A C6A C11A -0.81(18) . . . . ?
C4A C5A C6A C11A 177.67(12) . . . . ?
C5A C6A C7A C8A 179.82(13) . . . . ?
C11A C6A C7A C8A -0.3(2) . . . . ?
C6A C7A C8A C9A -0.6(3) . . . . ?
C7A C8A C9A C10A 0.8(5) . . . . ?
C8A C9A C10A C11A -0.1(5) . . . . ?
C9A C10A C11A N1A 179.0(3) . . . . ?
C9A C10A C11A C6A -0.7(3) . . . . ?
C7A C6A C11A N1A -178.76(13) . . . . ?
C5A C6A C11A N1A 1.1(2) . . . . ?
C7A C6A C11A C10A 0.9(2) . . . . ?
C5A C6A C11A C10A -179.19(12) . . . . ?
C10A C11A N1A C12A -179.81(12) . . . . ?
C6A C11A N1A C12A -0.1(2) . . . . ?
C11A N1A C12A C17A -1.15(19) . . . . ?
C11A N1A C12A C13A 178.58(12) . . . . ?
N1A C12A C13A C14A 179.58(12) . . . . ?
C17A C12A C13A C14A -0.68(19) . . . . ?
C12A C13A C14A C15A -2.50(19) . . . . ?
C12A C13A C14A C24A 174.97(12) . . . . ?
C13A C14A C15A C16A 4.02(18) . . . . ?
C24A C14A C15A C16A -173.42(11) . . . . ?
C13A C14A C15A S1A -179.61(10) . . . . ?
C24A C14A C15A S1A 2.95(19) . . . . ?
C1A S1A C15A C16A -0.42(10) . . . . ?
C1A S1A C15A C14A -177.10(13) . . . . ?
C14A C15A C16A C17A -2.42(19) . . . . ?
S1A C15A C16A C17A -179.53(10) . . . . ?
C14A C15A C16A C2A 176.85(11) . . . . ?
S1A C15A C16A C2A -0.25(14) . . . . ?
C1A C2A C16A C15A 0.99(17) . . . . ?
C3A C2A C16A C15A 179.88(11) . . . . ?
C1A C2A C16A C17A -179.73(12) . . . . ?
C3A C2A C16A C17A -0.85(19) . . . . ?
C6A C5A C17A C16A 178.95(11) . . . . ?
C4A C5A C17A C16A 0.35(18) . . . . ?
C6A C5A C17A C12A -0.39(18) . . . . ?
C4A C5A C17A C12A -178.99(11) . . . . ?
C15A C16A C17A C5A 179.78(11) . . . . ?
C2A C16A C17A C5A 0.55(19) . . . . ?
C15A C16A C17A C12A -0.86(19) . . . . ?
C2A C16A C17A C12A 179.92(11) . . . . ?
N1A C12A C17A C5A 1.46(19) . . . . ?
C13A C12A C17A C5A -178.27(11) . . . . ?
N1A C12A C17A C16A -177.88(11) . . . . ?
C13A C12A C17A C16A 2.38(18) . . . . ?
C4A C3A C18A C19A -54.42(18) . . . . ?
C2A C3A C18A C19A 125.47(14) . . . . ?
C4A C3A C18A C23A 125.17(14) . . . . ?
C2A C3A C18A C23A -54.94(17) . . . . ?
C23A C18A C19A C20A 1.5(2) . . . . ?
C3A C18A C19A C20A -178.92(13) . . . . ?
C18A C19A C20A C21A -0.5(2) . . . . ?
C19A C20A C21A C22A -1.0(2) . . . . ?
C20A C21A C22A C23A 1.6(2) . . . . ?
C21A C22A C23A C18A -0.6(2) . . . . ?
C19A C18A C23A C22A -0.9(2) . . . . ?
C3A C18A C23A C22A 179.50(12) . . . . ?
C13A C14A C24A C25A 145.53(13) . . . . ?
C15A C14A C24A C25A -37.11(18) . . . . ?
C13A C14A C24A C29A -35.34(18) . . . . ?
C15A C14A C24A C29A 142.02(13) . . . . ?
C29A C24A C25A C26A 0.7(2) . . . . ?
C14A C24A C25A C26A 179.81(12) . . . . ?
C24A C25A C26A C27A -1.2(2) . . . . ?
C25A C26A C27A C28A 0.4(2) . . . . ?
C26A C27A C28A C29A 0.9(2) . . . . ?
C27A C28A C29A C24A -1.5(2) . . . . ?
C25A C24A C29A C28A 0.7(2) . . . . ?
C14A C24A C29A C28A -178.50(13) . . . . ?
C15B S1B C1B C2B 24(3) . . . . ?
S1B C1B C2B C16B -21(4) . . . . ?
S1B C1B C2B C3B 168(4) . . . . ?
C1B C2B C3B C4B 161(4) . . . . ?
C16B C2B C3B C4B -10(5) . . . . ?
C1B C2B C3B C18B -16(6) . . . . ?
C16B C2B C3B C18B 174(3) . . . . ?
C2B C3B C4B C5B 0(6) . . . . ?
C18B C3B C4B C5B 177(3) . . . . ?
C3B C4B C5B C17B 4(6) . . . . ?
C3B C4B C5B C6B -177(5) . . . . ?
C17B C5B C6B C7B 173(4) . . . . ?
C4B C5B C6B C7B -6(8) . . . . ?
C17B C5B C6B C11B -2(7) . . . . ?
C4B C5B C6B C11B 179(4) . . . . ?
C11B C6B C7B C8B -9(7) . . . . ?
C5B C6B C7B C8B 176(5) . . . . ?
C6B C7B C8B C9B 6(11) . . . . ?
C7B C8B C9B C10B 3(18) . . . . ?
C8B C9B C10B C11B -8(17) . . . . ?
C9B C10B C11B N1B -178(9) . . . . ?
C9B C10B C11B C6B 5(11) . . . . ?
C7B C6B C11B N1B -173(5) . . . . ?
C5B C6B C11B N1B 2(8) . . . . ?
C7B C6B C11B C10B 3(8) . . . . ?
C5B C6B C11B C10B 178(5) . . . . ?
C10B C11B N1B C12B -179(4) . . . . ?
C6B C11B N1B C12B -2(7) . . . . ?
C11B N1B C12B C17B 3(6) . . . . ?
C11B N1B C12B C13B 180(4) . . . . ?
N1B C12B C13B C14B 176(4) . . . . ?
C17B C12B C13B C14B -7(6) . . . . ?
C12B C13B C14B C15B 6(5) . . . . ?
C12B C13B C14B C24B 180(3) . . . . ?
C13B C14B C15B C16B 0(5) . . . . ?
C24B C14B C15B C16B -173(3) . . . . ?
C13B C14B C15B S1B 178(3) . . . . ?
C24B C14B C15B S1B 5(5) . . . . ?
C1B S1B C15B C16B -19(3) . . . . ?
C1B S1B C15B C14B 163(4) . . . . ?
C14B C15B C16B C17B -6(6) . . . . ?
S1B C15B C16B C17B 176(3) . . . . ?
C14B C15B C16B C2B -171(4) . . . . ?
S1B C15B C16B C2B 11(4) . . . . ?
C1B C2B C16B C15B 6(5) . . . . ?
C3B C2B C16B C15B 179(4) . . . . ?
C1B C2B C16B C17B -159(4) . . . . ?
C3B C2B C16B C17B 14(5) . . . . ?
C6B C5B C17B C12B 2(6) . . . . ?
C4B C5B C17B C12B -179(4) . . . . ?
C6B C5B C17B C16B -179(4) . . . . ?
C4B C5B C17B C16B 0(6) . . . . ?
N1B C12B C17B C5B -3(7) . . . . ?
C13B C12B C17B C5B -180(4) . . . . ?
N1B C12B C17B C16B 178(4) . . . . ?
C13B C12B C17B C16B 1(6) . . . . ?
C15B C16B C17B C5B -174(4) . . . . ?
C2B C16B C17B C5B -9(6) . . . . ?
C15B C16B C17B C12B 5(6) . . . . ?
C2B C16B C17B C12B 170(4) . . . . ?
C4B C3B C18B C19B 146(3) . . . . ?
C2B C3B C18B C19B -37(4) . . . . ?
C4B C3B C18B C23B -39(4) . . . . ?
C2B C3B C18B C23B 138(3) . . . . ?
C23B C18B C19B C20B 0.0 . . . . ?
C3B C18B C19B C20B 175(3) . . . . ?
C18B C19B C20B C21B 0.0 . . . . ?
C19B C20B C21B C22B 0.0 . . . . ?
C20B C21B C22B C23B 0.0 . . . . ?
C21B C22B C23B C18B 0.0 . . . . ?
C19B C18B C23B C22B 0.0 . . . . ?
C3B C18B C23B C22B -175(2) . . . . ?
C13B C14B C24B C25B -48(3) . . . . ?
C15B C14B C24B C25B 125(3) . . . . ?
C13B C14B C24B C29B 128(3) . . . . ?
C15B C14B C24B C29B -60(3) . . . . ?
C29B C24B C25B C26B 0.0 . . . . ?
C14B C24B C25B C26B 175(2) . . . . ?
C24B C25B C26B C27B 0.0 . . . . ?
C25B C26B C27B C28B 0.0 . . . . ?
C26B C27B C28B C29B 0.0 . . . . ?
C27B C28B C29B C24B 0.0 . . . . ?
C25B C24B C29B C28B 0.0 . . . . ?
C14B C24B C29B C28B -175.2(19) . . . . ?

_refine_diff_density_max         0.495
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.052

