# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_S0707
_database_code_depnum_ccdc_archive 'CCDC 2081262'
loop_
_audit_author_name
_audit_author_address
'Jeffrey Ovens'
;University of Ottawa
Canada
;
_audit_update_record             
;
2021-04-30 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
#===============================================================================
# 5. CHEMICAL DATA

_chemical_name_systematic        
; 
;

_chemical_formula_sum            'C30 H32 N2 S4 Zn'
_chemical_formula_moiety         'C30 H32 N2 S4 Zn'
_chemical_formula_weight         614.18
#=============================================================
# 6. CRYSTAL DATA

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

#------------------------------------------------
_cell_length_a                   21.2905(10)
_cell_length_b                   7.6279(4)
_cell_length_c                   17.5124(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2844.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    5300
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      28.79

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.106
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_max          0.334

_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    1.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6723
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   SADABS

#=============================================================================
# 7. EXPERIMENTAL DATA

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω and φ scans'
_diffrn_ambient_temperature      203(2)
_diffrn_reflns_number            25606
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.913
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000


#==========================================================================
# 8. REFINEMENT DATA

_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_number_total             4339
_reflns_number_gt                2853
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_special_details          none

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details none
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         4339
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0302P)²+1.2930P] where P=(Fo²+2Fc²)/3'

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.062

#---------------------------------------------------------


#========================================================== 
# 9. General computing 

_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_cell_refinement       'Bruker SAINT'
_computing_structure_solution    
; 
 SHELXT 2014/5 (Sheldrick, 2014)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_shelx_SHELXL_version_number     2018/3

#===================================================================
# 10.  ATOMIC COORDINATES AND THERMAL PARAMETERS

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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'
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'
Zn Zn 0.2839 1.4301 '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'

#==============================================================================
# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

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
Zn1 Zn 0.500000 0.25520(4) 0.750000 0.03133(10) Uani 1 2 d S T P . .
S1 S 0.59330(3) 0.44611(7) 0.74273(3) 0.03510(13) Uani 1 1 d . . . . .
S2 S 0.42875(3) 0.36608(8) 0.54801(4) 0.04949(17) Uani 1 1 d . . . . .
N1 N 0.53042(8) 0.1561(2) 0.65593(9) 0.0315(4) Uani 1 1 d . . . . .
C1 C 0.56514(12) 0.6085(3) 0.67485(13) 0.0455(6) Uani 1 1 d . . . . .
H1A H 0.600641 0.661850 0.649044 0.068 Uiso 1 1 calc R U . . .
H1B H 0.541592 0.698183 0.701744 0.068 Uiso 1 1 calc R U . . .
H1C H 0.538174 0.552176 0.637561 0.068 Uiso 1 1 calc R U . . .
C2 C 0.63016(10) 0.2984(3) 0.67806(11) 0.0332(5) Uani 1 1 d . . . . .
C3 C 0.69388(11) 0.3166(3) 0.66379(14) 0.0440(6) Uani 1 1 d . . . . .
H3 H 0.717304 0.400740 0.690762 0.053 Uiso 1 1 calc R U . . .
C4 C 0.72305(13) 0.2122(3) 0.61037(16) 0.0521(7) Uani 1 1 d . . . . .
H4 H 0.766375 0.223261 0.601201 0.063 Uiso 1 1 calc R U . . .
C5 C 0.68776(12) 0.0910(3) 0.57042(15) 0.0488(6) Uani 1 1 d . . . . .
H5 H 0.707338 0.022050 0.532822 0.059 Uiso 1 1 calc R U . . .
C6 C 0.62472(11) 0.0688(3) 0.58433(12) 0.0384(5) Uani 1 1 d . . . . .
H6 H 0.602283 -0.016133 0.556580 0.046 Uiso 1 1 calc R U . . .
C7 C 0.59270(10) 0.1715(3) 0.63985(11) 0.0306(4) Uani 1 1 d . . . . .
C8 C 0.49349(10) 0.0431(3) 0.60649(12) 0.0354(5) Uani 1 1 d . . . . .
H8A H 0.507064 -0.078680 0.613365 0.042 Uiso 1 1 calc R U . . .
H8AB H 0.501052 0.075478 0.553129 0.042 Uiso 1 1 calc R U . . .
C9 C 0.42406(10) 0.0567(3) 0.62334(12) 0.0345(5) Uani 1 1 d . . . . .
C10 C 0.39396(11) -0.0759(3) 0.66400(13) 0.0410(5) Uani 1 1 d . . . . .
H10 H 0.417339 -0.174265 0.679446 0.049 Uiso 1 1 calc R U . . .
C11 C 0.33119(13) -0.0679(4) 0.68232(17) 0.0582(7) Uani 1 1 d . . . . .
H11 H 0.312261 -0.157306 0.711236 0.070 Uiso 1 1 calc R U . . .
C12 C 0.29677(13) 0.0731(4) 0.65754(16) 0.0573(7) Uani 1 1 d . . . . .
H12 H 0.253680 0.079285 0.668950 0.069 Uiso 1 1 calc R U . . .
C13 C 0.32468(12) 0.2068(3) 0.61589(14) 0.0467(6) Uani 1 1 d . . . . .
H13 H 0.300390 0.302055 0.598933 0.056 Uiso 1 1 calc R U . . .
C14 C 0.38847(11) 0.2003(3) 0.59915(12) 0.0369(5) Uani 1 1 d . . . . .
C15 C 0.36821(16) 0.5203(4) 0.52541(18) 0.0734(9) Uani 1 1 d . . . . .
H15A H 0.385817 0.615676 0.495669 0.110 Uiso 1 1 calc R U . . .
H15B H 0.350378 0.566449 0.572253 0.110 Uiso 1 1 calc R U . . .
H15C H 0.335610 0.462432 0.496055 0.110 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
Zn1 N1 1.9248(16) . ?
Zn1 N1 1.9248(16) 3_656 ?
Zn1 S1 2.4663(6) 3_656 ?
Zn1 S1 2.4664(6) . ?
S1 C2 1.780(2) . ?
S1 C1 1.819(2) . ?
S2 C14 1.771(2) . ?
S2 C15 1.790(3) . ?
N1 C7 1.361(3) . ?
N1 C8 1.453(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.386(3) . ?
C2 C7 1.422(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.375(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.423(3) . ?
C6 H6 0.9400 . ?
C8 C9 1.511(3) . ?
C8 H8A 0.9800 . ?
C8 H8AB 0.9800 . ?
C9 C10 1.393(3) . ?
C9 C14 1.398(3) . ?
C10 C11 1.376(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.372(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.387(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.390(3) . ?
C13 H13 0.9400 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?

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 Zn1 N1 133.75(11) . 3_656 ?
N1 Zn1 S1 123.17(5) . 3_656 ?
N1 Zn1 S1 85.22(5) 3_656 3_656 ?
N1 Zn1 S1 85.22(5) . . ?
N1 Zn1 S1 123.17(5) 3_656 . ?
S1 Zn1 S1 107.62(3) 3_656 . ?
C2 S1 C1 99.24(10) . . ?
C2 S1 Zn1 90.81(7) . . ?
C1 S1 Zn1 99.81(9) . . ?
C14 S2 C15 103.45(14) . . ?
C7 N1 C8 117.09(17) . . ?
C7 N1 Zn1 118.11(13) . . ?
C8 N1 Zn1 124.12(14) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 122.2(2) . . ?
C3 C2 S1 118.86(18) . . ?
C7 C2 S1 118.90(16) . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 121.4(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
N1 C7 C2 120.54(19) . . ?
N1 C7 C6 124.1(2) . . ?
C2 C7 C6 115.3(2) . . ?
N1 C8 C9 111.86(17) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8AB 109.2 . . ?
C9 C8 H8AB 109.2 . . ?
H8A C8 H8AB 107.9 . . ?
C10 C9 C14 118.3(2) . . ?
C10 C9 C8 120.0(2) . . ?
C14 C9 C8 121.7(2) . . ?
C11 C10 C9 122.3(2) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C12 C11 C10 118.7(2) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 119.6(2) . . ?
C13 C14 S2 123.64(18) . . ?
C9 C14 S2 116.76(18) . . ?
S2 C15 H15A 109.5 . . ?
S2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C1 S1 C2 C3 93.91(19) . . . . ?
Zn1 S1 C2 C3 -166.01(17) . . . . ?
C1 S1 C2 C7 -82.92(18) . . . . ?
Zn1 S1 C2 C7 17.16(15) . . . . ?
C7 C2 C3 C4 1.0(3) . . . . ?
S1 C2 C3 C4 -175.71(18) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 C6 -1.9(4) . . . . ?
C4 C5 C6 C7 0.9(4) . . . . ?
C8 N1 C7 C2 170.73(18) . . . . ?
Zn1 N1 C7 C2 -18.4(2) . . . . ?
C8 N1 C7 C6 -8.0(3) . . . . ?
Zn1 N1 C7 C6 162.95(16) . . . . ?
C3 C2 C7 N1 179.27(19) . . . . ?
S1 C2 C7 N1 -4.0(3) . . . . ?
C3 C2 C7 C6 -1.9(3) . . . . ?
S1 C2 C7 C6 174.78(15) . . . . ?
C5 C6 C7 N1 179.7(2) . . . . ?
C5 C6 C7 C2 1.0(3) . . . . ?
C7 N1 C8 C9 -172.05(18) . . . . ?
Zn1 N1 C8 C9 17.7(2) . . . . ?
N1 C8 C9 C10 -103.6(2) . . . . ?
N1 C8 C9 C14 76.3(2) . . . . ?
C14 C9 C10 C11 -1.5(3) . . . . ?
C8 C9 C10 C11 178.5(2) . . . . ?
C9 C10 C11 C12 2.1(4) . . . . ?
C10 C11 C12 C13 -1.0(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C9 1.2(3) . . . . ?
C12 C13 C14 S2 -178.75(19) . . . . ?
C10 C9 C14 C13 -0.2(3) . . . . ?
C8 C9 C14 C13 179.88(19) . . . . ?
C10 C9 C14 S2 179.74(16) . . . . ?
C8 C9 C14 S2 -0.2(3) . . . . ?
C15 S2 C14 C13 -1.6(2) . . . . ?
C15 S2 C14 C9 178.52(18) . . . . ?

####################################################################### 
# 
# 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_S0699
_database_code_depnum_ccdc_archive 'CCDC 2081263'
loop_
_audit_author_name
_audit_author_address
'Jeffrey Ovens'
;University of Ottawa
Canada
;
_audit_update_record             
;
2021-04-30 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
#===============================================================================
# 5. CHEMICAL DATA

_chemical_name_systematic        
; 
;

_chemical_formula_sum            'C28 H24 N2 S4 Zn'
_chemical_formula_moiety         'C28 H24 N2 S4 Zn'
_chemical_formula_weight         582.10
#=============================================================
# 6. CRYSTAL DATA

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

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

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

#------------------------------------------------
_cell_length_a                   7.1899(7)
_cell_length_b                   8.1002(8)
_cell_length_c                   44.714(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.341(3)
_cell_angle_gamma                90
_cell_volume                     2596.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    8665
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      23.46

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.071
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_max          0.101

_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    1.288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7105
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS

#=============================================================================
# 7. EXPERIMENTAL DATA

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω and φ scans'
_diffrn_ambient_temperature      203(2)
_diffrn_reflns_number            63086
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_av_R_equivalents  0.1333
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_theta_min         0.913
_diffrn_reflns_theta_max         27.649
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000


#==========================================================================
# 8. REFINEMENT DATA

_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_number_total             6027
_reflns_number_gt                3745
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_special_details          none

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details none
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         6027
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.0833
_refine_ls_wR_factor_gt          0.0685
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0208P)²+1.7130P] where P=(Fo²+2Fc²)/3'

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.090

#---------------------------------------------------------


#========================================================== 
# 9. General computing 

_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_cell_refinement       'Bruker SAINT'
_computing_structure_solution    
; 
 SHELXT 2014/5 (Sheldrick, 2014)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_shelx_SHELXL_version_number     2018/3

#===================================================================
# 10.  ATOMIC COORDINATES AND THERMAL PARAMETERS

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================
# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

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
Zn1 Zn 0.45955(5) 0.15648(4) 0.37347(2) 0.02370(10) Uani 1 1 d . . . . .
S1 S 0.71901(12) 0.20491(10) 0.40449(2) 0.0320(2) Uani 1 1 d . . . . .
S2 S 0.49290(14) 0.50708(14) 0.28287(2) 0.0482(3) Uani 1 1 d . . . . .
S3 S 0.45242(11) -0.00294(11) 0.33229(2) 0.0300(2) Uani 1 1 d . . . . .
S4 S 0.22280(12) -0.16070(11) 0.47244(2) 0.0358(2) Uani 1 1 d . . . . .
N1 N 0.4292(3) 0.4113(3) 0.36875(5) 0.0213(6) Uani 1 1 d . . . . .
N2 N 0.2182(3) 0.0349(3) 0.38606(5) 0.0199(6) Uani 1 1 d . . . . .
C1 C 0.4880(6) 0.5078(5) 0.24292(8) 0.0566(11) Uani 1 1 d . . . . .
H1A H 0.476310 0.395441 0.235512 0.085 Uiso 1 1 calc R U . . .
H1B H 0.602500 0.555951 0.236742 0.085 Uiso 1 1 calc R U . . .
H1C H 0.382387 0.572429 0.234774 0.085 Uiso 1 1 calc R U . . .
C2 C 0.2793(4) 0.4190(4) 0.29088(7) 0.0299(8) Uani 1 1 d . . . . .
C3 C 0.1488(5) 0.3561(5) 0.26945(8) 0.0423(9) Uani 1 1 d . . . . .
H3 H 0.168937 0.365525 0.248996 0.051 Uiso 1 1 calc R U . . .
C4 C -0.0093(6) 0.2805(5) 0.27790(9) 0.0512(11) Uani 1 1 d . . . . .
H4 H -0.096365 0.238948 0.263032 0.061 Uiso 1 1 calc R U . . .
C5 C -0.0443(5) 0.2635(4) 0.30789(9) 0.0454(10) Uani 1 1 d . . . . .
H5 H -0.152789 0.209989 0.313327 0.054 Uiso 1 1 calc R U . . .
C6 C 0.0840(4) 0.3272(4) 0.32969(8) 0.0322(8) Uani 1 1 d . . . . .
H6 H 0.062657 0.317277 0.350093 0.039 Uiso 1 1 calc R U . . .
C7 C 0.2442(5) 0.4056(4) 0.32126(7) 0.0264(8) Uani 1 1 d . . . . .
C8 C 0.3729(4) 0.4821(4) 0.34408(7) 0.0258(7) Uani 1 1 d . . . . .
H8 H 0.416837 0.588951 0.340447 0.031 Uiso 1 1 calc R U . . .
C9 C 0.5398(4) 0.5025(4) 0.39111(6) 0.0224(7) Uani 1 1 d . . . . .
C10 C 0.5051(4) 0.6680(4) 0.39635(7) 0.0276(7) Uani 1 1 d . . . . .
H10 H 0.406966 0.721567 0.385143 0.033 Uiso 1 1 calc R U . . .
C11 C 0.6125(5) 0.7546(4) 0.41775(7) 0.0303(8) Uani 1 1 d . . . . .
H11 H 0.586944 0.866305 0.421419 0.036 Uiso 1 1 calc R U . . .
C12 C 0.7587(4) 0.6755(4) 0.43382(7) 0.0285(8) Uani 1 1 d . . . . .
H12 H 0.836141 0.735015 0.447862 0.034 Uiso 1 1 calc R U . . .
C13 C 0.7914(4) 0.5094(4) 0.42931(7) 0.0271(7) Uani 1 1 d . . . . .
H13 H 0.890547 0.457243 0.440528 0.033 Uiso 1 1 calc R U . . .
C14 C 0.6801(4) 0.4174(4) 0.40844(7) 0.0231(7) Uani 1 1 d . . . . .
C15 C 0.2037(5) -0.1848(5) 0.51207(7) 0.0434(10) Uani 1 1 d . . . . .
H15A H 0.114860 -0.105369 0.518770 0.065 Uiso 1 1 calc R U . . .
H15B H 0.324639 -0.166277 0.522692 0.065 Uiso 1 1 calc R U . . .
H15C H 0.161478 -0.295699 0.516136 0.065 Uiso 1 1 calc R U . . .
C16 C 0.2549(4) 0.0523(4) 0.46779(7) 0.0250(7) Uani 1 1 d . . . . .
C17 C 0.3036(4) 0.1577(4) 0.49149(7) 0.0310(8) Uani 1 1 d . . . . .
H17 H 0.319277 0.115441 0.511096 0.037 Uiso 1 1 calc R U . . .
C18 C 0.3294(4) 0.3243(5) 0.48662(8) 0.0376(9) Uani 1 1 d . . . . .
H18 H 0.362046 0.394335 0.502941 0.045 Uiso 1 1 calc R U . . .
C19 C 0.3076(4) 0.3889(4) 0.45789(8) 0.0342(8) Uani 1 1 d . . . . .
H19 H 0.326435 0.502082 0.454623 0.041 Uiso 1 1 calc R U . . .
C20 C 0.2577(4) 0.2852(4) 0.43405(7) 0.0296(8) Uani 1 1 d . . . . .
H20 H 0.240903 0.329169 0.414579 0.035 Uiso 1 1 calc R U . . .
C21 C 0.2322(4) 0.1181(4) 0.43837(7) 0.0216(7) Uani 1 1 d . . . . .
C22 C 0.1711(4) 0.0124(4) 0.41290(6) 0.0236(7) Uani 1 1 d . . . . .
H22 H 0.092693 -0.077333 0.416410 0.028 Uiso 1 1 calc R U . . .
C23 C 0.1318(4) -0.0621(4) 0.36216(7) 0.0216(7) Uani 1 1 d . . . . .
C24 C -0.0441(4) -0.1317(4) 0.36360(7) 0.0289(8) Uani 1 1 d . . . . .
H24 H -0.110492 -0.113697 0.380625 0.035 Uiso 1 1 calc R U . . .
C25 C -0.1223(4) -0.2271(4) 0.34030(8) 0.0335(8) Uani 1 1 d . . . . .
H25 H -0.239483 -0.276686 0.341798 0.040 Uiso 1 1 calc R U . . .
C26 C -0.0280(5) -0.2494(4) 0.31481(7) 0.0322(8) Uani 1 1 d . . . . .
H26 H -0.080759 -0.314488 0.298952 0.039 Uiso 1 1 calc R U . . .
C27 C 0.1430(4) -0.1763(4) 0.31265(7) 0.0280(8) Uani 1 1 d . . . . .
H27 H 0.204345 -0.190034 0.294987 0.034 Uiso 1 1 calc R U . . .
C28 C 0.2278(4) -0.0823(4) 0.33595(6) 0.0210(7) 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
Zn1 N1 2.085(2) . ?
Zn1 N2 2.108(2) . ?
Zn1 S3 2.2467(9) . ?
Zn1 S1 2.2728(9) . ?
S1 C14 1.755(3) . ?
S2 C2 1.755(3) . ?
S2 C1 1.784(3) . ?
S3 C28 1.757(3) . ?
S4 C16 1.755(3) . ?
S4 C15 1.798(3) . ?
N1 C8 1.281(4) . ?
N1 C9 1.434(4) . ?
N2 C22 1.284(3) . ?
N2 C23 1.430(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.386(4) . ?
C2 C7 1.405(4) . ?
C3 C4 1.369(5) . ?
C3 H3 0.9400 . ?
C4 C5 1.390(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.390(5) . ?
C5 H5 0.9400 . ?
C6 C7 1.392(4) . ?
C6 H6 0.9400 . ?
C7 C8 1.462(4) . ?
C8 H8 0.9400 . ?
C9 C10 1.386(4) . ?
C9 C14 1.406(4) . ?
C10 C11 1.376(4) . ?
C10 H10 0.9400 . ?
C11 C12 1.385(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.384(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.398(4) . ?
C13 H13 0.9400 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 C17 1.385(4) . ?
C16 C21 1.417(4) . ?
C17 C18 1.381(5) . ?
C17 H17 0.9400 . ?
C18 C19 1.385(5) . ?
C18 H18 0.9400 . ?
C19 C20 1.383(4) . ?
C19 H19 0.9400 . ?
C20 C21 1.382(4) . ?
C20 H20 0.9400 . ?
C21 C22 1.466(4) . ?
C22 H22 0.9400 . ?
C23 C24 1.390(4) . ?
C23 C28 1.414(4) . ?
C24 C25 1.382(4) . ?
C24 H24 0.9400 . ?
C25 C26 1.382(4) . ?
C25 H25 0.9400 . ?
C26 C27 1.375(4) . ?
C26 H26 0.9400 . ?
C27 C28 1.393(4) . ?
C27 H27 0.9400 . ?

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 Zn1 N2 114.04(9) . . ?
N1 Zn1 S3 119.36(7) . . ?
N2 Zn1 S3 88.98(7) . . ?
N1 Zn1 S1 88.04(7) . . ?
N2 Zn1 S1 124.88(7) . . ?
S3 Zn1 S1 124.48(3) . . ?
C14 S1 Zn1 95.79(11) . . ?
C2 S2 C1 104.72(18) . . ?
C28 S3 Zn1 95.62(10) . . ?
C16 S4 C15 104.12(17) . . ?
C8 N1 C9 119.5(3) . . ?
C8 N1 Zn1 123.6(2) . . ?
C9 N1 Zn1 113.01(18) . . ?
C22 N2 C23 119.3(3) . . ?
C22 N2 Zn1 126.6(2) . . ?
C23 N2 Zn1 112.14(18) . . ?
S2 C1 H1A 109.5 . . ?
S2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.6(3) . . ?
C3 C2 S2 124.4(3) . . ?
C7 C2 S2 116.9(2) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 118.7(4) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 120.6(3) . . ?
C6 C7 C8 119.8(3) . . ?
C2 C7 C8 119.4(3) . . ?
N1 C8 C7 123.6(3) . . ?
N1 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
C10 C9 C14 120.8(3) . . ?
C10 C9 N1 121.2(3) . . ?
C14 C9 N1 118.0(3) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.3(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 121.4(3) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C9 117.2(3) . . ?
C13 C14 S1 120.2(2) . . ?
C9 C14 S1 122.6(2) . . ?
S4 C15 H15A 109.5 . . ?
S4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 118.9(3) . . ?
C17 C16 S4 122.9(3) . . ?
C21 C16 S4 118.2(2) . . ?
C18 C17 C16 120.7(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 120.5(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 119.4(3) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C21 C20 C19 121.1(3) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C16 119.4(3) . . ?
C20 C21 C22 119.9(3) . . ?
C16 C21 C22 120.5(3) . . ?
N2 C22 C21 123.9(3) . . ?
N2 C22 H22 118.0 . . ?
C21 C22 H22 118.0 . . ?
C24 C23 C28 119.6(3) . . ?
C24 C23 N2 122.2(3) . . ?
C28 C23 N2 118.1(3) . . ?
C25 C24 C23 120.8(3) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C27 C26 C25 119.9(3) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 121.7(3) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 H27 119.1 . . ?
C27 C28 C23 118.0(3) . . ?
C27 C28 S3 118.9(2) . . ?
C23 C28 S3 123.0(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
C1 S2 C2 C3 4.0(4) . . . . ?
C1 S2 C2 C7 -179.0(3) . . . . ?
C7 C2 C3 C4 -1.0(5) . . . . ?
S2 C2 C3 C4 176.0(3) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C4 C5 C6 C7 -0.2(5) . . . . ?
C5 C6 C7 C2 -1.0(5) . . . . ?
C5 C6 C7 C8 176.0(3) . . . . ?
C3 C2 C7 C6 1.6(5) . . . . ?
S2 C2 C7 C6 -175.6(2) . . . . ?
C3 C2 C7 C8 -175.4(3) . . . . ?
S2 C2 C7 C8 7.4(4) . . . . ?
C9 N1 C8 C7 -173.5(3) . . . . ?
Zn1 N1 C8 C7 30.2(4) . . . . ?
C6 C7 C8 N1 46.3(4) . . . . ?
C2 C7 C8 N1 -136.6(3) . . . . ?
C8 N1 C9 C10 37.5(4) . . . . ?
Zn1 N1 C9 C10 -163.9(2) . . . . ?
C8 N1 C9 C14 -145.0(3) . . . . ?
Zn1 N1 C9 C14 13.6(3) . . . . ?
C14 C9 C10 C11 2.9(5) . . . . ?
N1 C9 C10 C11 -179.7(3) . . . . ?
C9 C10 C11 C12 1.0(5) . . . . ?
C10 C11 C12 C13 -2.8(5) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 C9 3.2(4) . . . . ?
C12 C13 C14 S1 -177.2(2) . . . . ?
C10 C9 C14 C13 -4.9(4) . . . . ?
N1 C9 C14 C13 177.6(3) . . . . ?
C10 C9 C14 S1 175.5(2) . . . . ?
N1 C9 C14 S1 -2.0(4) . . . . ?
Zn1 S1 C14 C13 171.5(2) . . . . ?
Zn1 S1 C14 C9 -8.9(3) . . . . ?
C15 S4 C16 C17 15.2(3) . . . . ?
C15 S4 C16 C21 -165.7(2) . . . . ?
C21 C16 C17 C18 0.1(4) . . . . ?
S4 C16 C17 C18 179.2(2) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C20 0.6(5) . . . . ?
C18 C19 C20 C21 -1.0(5) . . . . ?
C19 C20 C21 C16 0.9(5) . . . . ?
C19 C20 C21 C22 177.2(3) . . . . ?
C17 C16 C21 C20 -0.5(4) . . . . ?
S4 C16 C21 C20 -179.6(2) . . . . ?
C17 C16 C21 C22 -176.7(3) . . . . ?
S4 C16 C21 C22 4.1(4) . . . . ?
C23 N2 C22 C21 -171.9(3) . . . . ?
Zn1 N2 C22 C21 25.2(4) . . . . ?
C20 C21 C22 N2 34.0(4) . . . . ?
C16 C21 C22 N2 -149.7(3) . . . . ?
C22 N2 C23 C24 25.2(4) . . . . ?
Zn1 N2 C23 C24 -169.5(2) . . . . ?
C22 N2 C23 C28 -156.8(3) . . . . ?
Zn1 N2 C23 C28 8.4(3) . . . . ?
C28 C23 C24 C25 3.1(5) . . . . ?
N2 C23 C24 C25 -179.0(3) . . . . ?
C23 C24 C25 C26 -2.2(5) . . . . ?
C24 C25 C26 C27 -0.2(5) . . . . ?
C25 C26 C27 C28 1.6(5) . . . . ?
C26 C27 C28 C23 -0.6(5) . . . . ?
C26 C27 C28 S3 176.4(2) . . . . ?
C24 C23 C28 C27 -1.7(4) . . . . ?
N2 C23 C28 C27 -179.7(3) . . . . ?
C24 C23 C28 S3 -178.6(2) . . . . ?
N2 C23 C28 S3 3.4(4) . . . . ?
Zn1 S3 C28 C27 171.4(2) . . . . ?
Zn1 S3 C28 C23 -11.8(3) . . . . ?

####################################################################### 
# 
# 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_S0811
_database_code_depnum_ccdc_archive 'CCDC 2081265'
loop_
_audit_author_name
_audit_author_address
'Jeffrey Ovens'
;University of Ottawa
Canada
;
_audit_update_record             
;
2021-04-30 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
#===============================================================================
# 5. CHEMICAL DATA

_chemical_name_systematic        
; 
;

_chemical_formula_sum            'C29 H28 N2 S4 Zn'
_chemical_formula_moiety         'C29 H28 N2 S4 Zn'
_chemical_formula_weight         598.14
#=============================================================
# 6. 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                   10.7382(9)
_cell_length_b                   11.2465(11)
_cell_length_c                   12.8901(12)
_cell_angle_alpha                68.170(3)
_cell_angle_beta                 68.707(3)
_cell_angle_gamma                87.560(3)
_cell_volume                     1338.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    7925
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.18

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.046
_exptl_crystal_size_mid          0.291
_exptl_crystal_size_max          0.345

_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             620
_exptl_absorpt_coefficient_mu    1.252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6941
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS

#=============================================================================
# 7. EXPERIMENTAL DATA

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω and φ scans'
_diffrn_ambient_temperature      203(2)
_diffrn_reflns_number            28566
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.835
_diffrn_reflns_theta_max         27.722
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000


#==========================================================================
# 8. REFINEMENT DATA

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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_number_total             6216
_reflns_number_gt                4286
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_special_details          none

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details none
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         6216
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.0871
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+0.3542P] where P=(Fo²+2Fc²)/3'

#---------------------------------------------------------


#========================================================== 
# 9. General computing 

_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_cell_refinement       'Bruker SAINT'
_computing_structure_solution    
; 
 SHELXT 2014/5 (Sheldrick, 2014)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_shelx_SHELXL_version_number     2018/3

#===================================================================
# 10.  ATOMIC COORDINATES AND THERMAL PARAMETERS

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================
# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

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
Zn1 Zn 0.69554(3) 0.77492(3) 0.62098(3) 0.02414(10) Uani 1 1 d . . . . .
S1 S 0.84934(7) 0.94356(7) 0.43271(7) 0.02724(17) Uani 1 1 d . . . . .
S2 S 0.85704(8) 0.47236(8) 0.63086(7) 0.0389(2) Uani 1 1 d . . . . .
S3 S 0.77792(7) 0.75466(7) 0.76400(7) 0.02976(18) Uani 1 1 d . . . . .
S4 S 0.15326(8) 0.69107(8) 0.91953(7) 0.0371(2) Uani 1 1 d . . . . .
N006 N 0.6865(2) 0.6903(2) 0.51844(19) 0.0215(5) Uani 1 1 d . . . . .
N007 N 0.5395(2) 0.8661(2) 0.7068(2) 0.0236(5) Uani 1 1 d . . . . .
C1 C 0.9969(3) 0.8639(3) 0.4457(3) 0.0354(7) Uani 1 1 d . . . . .
H1A H 1.071872 0.898745 0.368968 0.053 Uiso 1 1 calc R U . . .
H1B H 0.978230 0.772152 0.468346 0.053 Uiso 1 1 calc R U . . .
H1C H 1.019371 0.878200 0.506877 0.053 Uiso 1 1 calc R U . . .
C2 C 0.8085(3) 0.8780(3) 0.3414(2) 0.0230(6) Uani 1 1 d . . . . .
C3 C 0.8573(3) 0.9464(3) 0.2178(3) 0.0302(7) Uani 1 1 d . . . . .
H3 H 0.910228 1.025698 0.184571 0.036 Uiso 1 1 calc R U . . .
C4 C 0.8292(3) 0.8998(3) 0.1428(3) 0.0330(7) Uani 1 1 d . . . . .
H4 H 0.863107 0.945690 0.058936 0.040 Uiso 1 1 calc R U . . .
C5 C 0.7494(3) 0.7830(3) 0.1946(3) 0.0300(7) Uani 1 1 d . . . . .
H5 H 0.728467 0.750668 0.144661 0.036 Uiso 1 1 calc R U . . .
C6 C 0.7003(3) 0.7136(3) 0.3171(2) 0.0238(6) Uani 1 1 d . . . . .
H6 H 0.646214 0.635321 0.348688 0.029 Uiso 1 1 calc R U . . .
C7 C 0.7292(2) 0.7570(2) 0.3969(2) 0.0202(6) Uani 1 1 d . . . . .
C8 C 0.6142(3) 0.5625(2) 0.5674(2) 0.0247(6) Uani 1 1 d . . . . .
H8A H 0.667259 0.510600 0.524099 0.030 Uiso 1 1 calc R U . . .
H8AB H 0.528423 0.570307 0.556009 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5886(3) 0.4966(2) 0.6995(2) 0.0222(6) Uani 1 1 d . . . . .
C10 C 0.4596(3) 0.4820(3) 0.7847(3) 0.0270(7) Uani 1 1 d . . . . .
H10 H 0.389185 0.512647 0.758366 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4319(3) 0.4238(3) 0.9068(3) 0.0343(7) Uani 1 1 d . . . . .
H11 H 0.343885 0.415184 0.962712 0.041 Uiso 1 1 calc R U . . .
C12 C 0.5345(3) 0.3785(3) 0.9457(3) 0.0341(7) Uani 1 1 d . . . . .
H12 H 0.516127 0.338033 1.028729 0.041 Uiso 1 1 calc R U . . .
C13 C 0.6643(3) 0.3918(3) 0.8641(3) 0.0316(7) Uani 1 1 d . . . . .
H13 H 0.733796 0.361485 0.891930 0.038 Uiso 1 1 calc R U . . .
C14 C 0.6927(3) 0.4500(3) 0.7405(2) 0.0245(6) Uani 1 1 d . . . . .
C15 C 0.9500(3) 0.3741(3) 0.7152(3) 0.0485(9) Uani 1 1 d . . . . .
H15A H 1.040229 0.373532 0.660708 0.073 Uiso 1 1 calc R U . . .
H15B H 0.905568 0.286855 0.758136 0.073 Uiso 1 1 calc R U . . .
H15C H 0.954597 0.408639 0.772539 0.073 Uiso 1 1 calc R U . . .
C16 C 0.7002(3) 0.8859(3) 0.7938(2) 0.0232(6) Uani 1 1 d . . . . .
C17 C 0.7441(3) 0.9471(3) 0.8519(3) 0.0318(7) Uani 1 1 d . . . . .
H17 H 0.816386 0.917412 0.875854 0.038 Uiso 1 1 calc R U . . .
C18 C 0.6846(3) 1.0504(3) 0.8758(3) 0.0385(8) Uani 1 1 d . . . . .
H18 H 0.716449 1.089766 0.915422 0.046 Uiso 1 1 calc R U . . .
C19 C 0.5781(3) 1.0959(3) 0.8413(3) 0.0370(8) Uani 1 1 d . . . . .
H19 H 0.538598 1.167171 0.855945 0.044 Uiso 1 1 calc R U . . .
C20 C 0.5306(3) 1.0360(3) 0.7856(3) 0.0319(7) Uani 1 1 d . . . . .
H20 H 0.458147 1.066366 0.762157 0.038 Uiso 1 1 calc R U . . .
C21 C 0.5891(3) 0.9304(3) 0.7634(2) 0.0230(6) Uani 1 1 d . . . . .
C22 C 0.4111(3) 0.8477(3) 0.7400(3) 0.0269(7) Uani 1 1 d . . . . .
H22 H 0.358007 0.873384 0.802548 0.032 Uiso 1 1 calc R U . . .
C23 C 0.3408(3) 0.7907(3) 0.6896(3) 0.0254(6) Uani 1 1 d . . . . .
C24 C 0.3950(3) 0.8073(3) 0.5682(3) 0.0317(7) Uani 1 1 d . . . . .
H24 H 0.479269 0.854951 0.517981 0.038 Uiso 1 1 calc R U . . .
C25 C 0.3254(3) 0.7539(3) 0.5214(3) 0.0375(8) Uani 1 1 d . . . . .
H25 H 0.362358 0.764779 0.439857 0.045 Uiso 1 1 calc R U . . .
C26 C 0.2010(3) 0.6844(3) 0.5959(3) 0.0405(8) Uani 1 1 d . . . . .
H26 H 0.154004 0.647465 0.564345 0.049 Uiso 1 1 calc R U . . .
C27 C 0.1450(3) 0.6686(3) 0.7150(3) 0.0345(7) Uani 1 1 d . . . . .
H27 H 0.059618 0.622550 0.763554 0.041 Uiso 1 1 calc R U . . .
C28 C 0.2135(3) 0.7199(3) 0.7645(3) 0.0277(7) Uani 1 1 d . . . . .
C29 C -0.0255(3) 0.6714(3) 0.9645(3) 0.0457(9) Uani 1 1 d . . . . .
H29A H -0.052418 0.739257 0.906360 0.069 Uiso 1 1 calc R U . . .
H29B H -0.068133 0.675835 1.043258 0.069 Uiso 1 1 calc R U . . .
H29C H -0.052982 0.588300 0.968293 0.069 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
Zn1 N006 1.923(2) . ?
Zn1 N007 2.106(2) . ?
Zn1 S3 2.2556(8) . ?
Zn1 S1 2.4793(8) . ?
S1 C2 1.780(3) . ?
S1 C1 1.817(3) . ?
S2 C14 1.771(3) . ?
S2 C15 1.789(3) . ?
S3 C16 1.762(3) . ?
S4 C28 1.765(3) . ?
S4 C29 1.790(3) . ?
N006 C7 1.364(3) . ?
N006 C8 1.460(3) . ?
N007 C22 1.287(3) . ?
N007 C21 1.431(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.387(4) . ?
C2 C7 1.421(4) . ?
C3 C4 1.379(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.376(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.418(3) . ?
C6 H6 0.9400 . ?
C8 C9 1.504(4) . ?
C8 H8A 0.9800 . ?
C8 H8AB 0.9800 . ?
C9 C10 1.390(4) . ?
C9 C14 1.405(4) . ?
C10 C11 1.380(4) . ?
C10 H10 0.9400 . ?
C11 C12 1.374(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.381(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.396(4) . ?
C13 H13 0.9400 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 C17 1.388(4) . ?
C16 C21 1.404(4) . ?
C17 C18 1.383(4) . ?
C17 H17 0.9400 . ?
C18 C19 1.385(4) . ?
C18 H18 0.9400 . ?
C19 C20 1.373(4) . ?
C19 H19 0.9400 . ?
C20 C21 1.394(4) . ?
C20 H20 0.9400 . ?
C22 C23 1.452(4) . ?
C22 H22 0.9400 . ?
C23 C24 1.397(4) . ?
C23 C28 1.413(4) . ?
C24 C25 1.384(4) . ?
C24 H24 0.9400 . ?
C25 C26 1.385(4) . ?
C25 H25 0.9400 . ?
C26 C27 1.374(4) . ?
C26 H26 0.9400 . ?
C27 C28 1.390(4) . ?
C27 H27 0.9400 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 H29C 0.9700 . ?

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
N006 Zn1 N007 125.30(9) . . ?
N006 Zn1 S3 141.00(7) . . ?
N007 Zn1 S3 87.34(6) . . ?
N006 Zn1 S1 85.34(7) . . ?
N007 Zn1 S1 107.56(6) . . ?
S3 Zn1 S1 106.18(3) . . ?
C2 S1 C1 101.09(13) . . ?
C2 S1 Zn1 92.10(9) . . ?
C1 S1 Zn1 92.62(10) . . ?
C14 S2 C15 103.54(15) . . ?
C16 S3 Zn1 93.47(9) . . ?
C28 S4 C29 103.56(15) . . ?
C7 N006 C8 117.4(2) . . ?
C7 N006 Zn1 120.00(17) . . ?
C8 N006 Zn1 121.79(17) . . ?
C22 N007 C21 117.2(2) . . ?
C22 N007 Zn1 131.34(19) . . ?
C21 N007 Zn1 108.85(16) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 122.2(3) . . ?
C3 C2 S1 118.5(2) . . ?
C7 C2 S1 119.3(2) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 121.8(3) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
N006 C7 C6 124.2(2) . . ?
N006 C7 C2 120.7(2) . . ?
C6 C7 C2 115.1(2) . . ?
N006 C8 C9 110.5(2) . . ?
N006 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N006 C8 H8AB 109.5 . . ?
C9 C8 H8AB 109.5 . . ?
H8A C8 H8AB 108.1 . . ?
C10 C9 C14 118.3(3) . . ?
C10 C9 C8 120.0(2) . . ?
C14 C9 C8 121.7(2) . . ?
C11 C10 C9 121.9(3) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 119.6(3) . . ?
C13 C14 S2 122.7(2) . . ?
C9 C14 S2 117.7(2) . . ?
S2 C15 H15A 109.5 . . ?
S2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 117.2(3) . . ?
C17 C16 S3 121.1(2) . . ?
C21 C16 S3 121.7(2) . . ?
C18 C17 C16 121.9(3) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 119.4(3) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.9(3) . . ?
C20 C21 N007 121.0(3) . . ?
C16 C21 N007 118.1(2) . . ?
N007 C22 C23 125.9(3) . . ?
N007 C22 H22 117.1 . . ?
C23 C22 H22 117.1 . . ?
C24 C23 C28 119.5(3) . . ?
C24 C23 C22 121.4(3) . . ?
C28 C23 C22 119.1(3) . . ?
C25 C24 C23 120.5(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 119.4(3) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C27 C26 C25 121.0(3) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 120.7(3) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C27 C28 C23 118.9(3) . . ?
C27 C28 S4 122.6(2) . . ?
C23 C28 S4 118.4(2) . . ?
S4 C29 H29A 109.5 . . ?
S4 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
S4 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
C1 S1 C2 C3 -94.5(2) . . . . ?
Zn1 S1 C2 C3 172.4(2) . . . . ?
C1 S1 C2 C7 84.5(2) . . . . ?
Zn1 S1 C2 C7 -8.5(2) . . . . ?
C7 C2 C3 C4 0.7(4) . . . . ?
S1 C2 C3 C4 179.7(2) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
C8 N006 C7 C6 4.3(4) . . . . ?
Zn1 N006 C7 C6 -165.55(19) . . . . ?
C8 N006 C7 C2 -175.5(2) . . . . ?
Zn1 N006 C7 C2 14.7(3) . . . . ?
C5 C6 C7 N006 -178.0(2) . . . . ?
C5 C6 C7 C2 1.7(4) . . . . ?
C3 C2 C7 N006 177.9(2) . . . . ?
S1 C2 C7 N006 -1.1(3) . . . . ?
C3 C2 C7 C6 -1.9(4) . . . . ?
S1 C2 C7 C6 179.12(18) . . . . ?
C7 N006 C8 C9 173.4(2) . . . . ?
Zn1 N006 C8 C9 -16.9(3) . . . . ?
N006 C8 C9 C10 107.2(3) . . . . ?
N006 C8 C9 C14 -71.9(3) . . . . ?
C14 C9 C10 C11 0.1(4) . . . . ?
C8 C9 C10 C11 -179.1(2) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C9 0.8(4) . . . . ?
C12 C13 C14 S2 179.1(2) . . . . ?
C10 C9 C14 C13 -0.4(4) . . . . ?
C8 C9 C14 C13 178.7(2) . . . . ?
C10 C9 C14 S2 -178.7(2) . . . . ?
C8 C9 C14 S2 0.4(3) . . . . ?
C15 S2 C14 C13 12.8(3) . . . . ?
C15 S2 C14 C9 -168.9(2) . . . . ?
Zn1 S3 C16 C17 -161.1(2) . . . . ?
Zn1 S3 C16 C21 21.0(2) . . . . ?
C21 C16 C17 C18 -2.2(4) . . . . ?
S3 C16 C17 C18 179.8(2) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
C17 C18 C19 C20 1.3(5) . . . . ?
C18 C19 C20 C21 -0.2(5) . . . . ?
C19 C20 C21 C16 -2.2(4) . . . . ?
C19 C20 C21 N007 179.2(3) . . . . ?
C17 C16 C21 C20 3.3(4) . . . . ?
S3 C16 C21 C20 -178.7(2) . . . . ?
C17 C16 C21 N007 -178.1(2) . . . . ?
S3 C16 C21 N007 -0.1(4) . . . . ?
C22 N007 C21 C20 -41.3(4) . . . . ?
Zn1 N007 C21 C20 154.9(2) . . . . ?
C22 N007 C21 C16 140.0(3) . . . . ?
Zn1 N007 C21 C16 -23.8(3) . . . . ?
C21 N007 C22 C23 176.6(3) . . . . ?
Zn1 N007 C22 C23 -24.0(4) . . . . ?
N007 C22 C23 C24 -32.4(4) . . . . ?
N007 C22 C23 C28 149.2(3) . . . . ?
C28 C23 C24 C25 -0.6(4) . . . . ?
C22 C23 C24 C25 -179.0(3) . . . . ?
C23 C24 C25 C26 0.4(4) . . . . ?
C24 C25 C26 C27 0.6(5) . . . . ?
C25 C26 C27 C28 -1.3(5) . . . . ?
C26 C27 C28 C23 1.1(4) . . . . ?
C26 C27 C28 S4 -174.4(2) . . . . ?
C24 C23 C28 C27 -0.1(4) . . . . ?
C22 C23 C28 C27 178.3(3) . . . . ?
C24 C23 C28 S4 175.6(2) . . . . ?
C22 C23 C28 S4 -6.0(3) . . . . ?
C29 S4 C28 C27 -30.5(3) . . . . ?
C29 S4 C28 C23 154.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1C S1 0.97 2.97 3.818(3) 146.9 2_776 yes
C13 H13 S4 0.94 2.96 3.790(3) 148.6 2_667 yes
C29 H29A S3 0.97 2.98 3.742(3) 136.3 1_455 yes
C29 H29C S4 0.97 2.98 3.897(3) 157.4 2_567 yes

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_S0927
_database_code_depnum_ccdc_archive 'CCDC 2081266'
loop_
_audit_author_name
_audit_author_address
'Jeffrey Ovens'
;University of Ottawa
Canada
;
_audit_update_record             
;
2021-04-30 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
#===============================================================================
# 5. CHEMICAL DATA

_chemical_name_systematic        
; 
;

_chemical_formula_sum            'C21 H19 N S2'
_chemical_formula_moiety         'C21 H19 N S2'
_chemical_formula_weight         349.49
#=============================================================
# 6. CRYSTAL DATA

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

#------------------------------------------------
_cell_length_a                   18.558(3)
_cell_length_b                   9.2607(14)
_cell_length_c                   10.3515(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1779.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    4332
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      25.17

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.06
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_max          0.342

_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5600
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS

#=============================================================================
# 7. EXPERIMENTAL DATA

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω and φ scans'
_diffrn_ambient_temperature      203(2)
_diffrn_reflns_number            10688
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.195
_diffrn_reflns_theta_max         25.704
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.982


#==========================================================================
# 8. REFINEMENT DATA

_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_number_total             3304
_reflns_number_gt                2681
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_max     0.955
_reflns_Friedel_fraction_full    0.962

_refine_special_details          none

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1029 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3304
_refine_ls_number_parameters     218
_refine_ls_number_restraints     183
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1522
_refine_ls_wR_factor_gt          0.1415
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0887P)²+0.3504P] where P=(Fo²+2Fc²)/3'

#---------------------------------------------------------


#========================================================== 
# 9. General computing 

_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_cell_refinement       'Bruker SAINT'
_computing_structure_solution    
; 
 SHELXT 2014/5 (Sheldrick, 2014)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_shelx_SHELXL_version_number     2018/3

#===================================================================
# 10.  ATOMIC COORDINATES AND THERMAL PARAMETERS

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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'

#==============================================================================
# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

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 0.36176(7) 0.13684(18) 0.65569(15) 0.0462(4) Uani 1 1 d . . . . .
S2 S 0.63103(8) 0.59590(19) 0.49266(19) 0.0539(5) Uani 1 1 d . . . . .
N1 N 0.4488(2) 0.3003(5) 0.5198(4) 0.0346(9) Uani 1 1 d . . . . .
C1 C 0.7208(4) 0.6560(9) 0.4599(9) 0.077(2) Uani 1 1 d . . . . .
H1A H 0.720731 0.717094 0.383793 0.115 Uiso 1 1 calc R U . . .
H1B H 0.751678 0.573124 0.445016 0.115 Uiso 1 1 calc R U . . .
H1C H 0.738781 0.710472 0.533236 0.115 Uiso 1 1 calc R U . . .
C2 C 0.6118(3) 0.4725(6) 0.3663(6) 0.0404(12) Uani 1 1 d . . . . .
C3 C 0.6538(3) 0.4585(7) 0.2566(6) 0.0518(14) Uani 1 1 d . . . . .
H3 H 0.695040 0.516150 0.245723 0.062 Uiso 1 1 calc R U . . .
C4 C 0.6344(3) 0.3579(8) 0.1621(7) 0.0544(14) Uani 1 1 d . . . . .
H4 H 0.662856 0.348799 0.087405 0.065 Uiso 1 1 calc R U . . .
C5 C 0.5756(3) 0.2735(7) 0.1762(5) 0.0487(13) Uani 1 1 d . . . . .
H5 H 0.563383 0.205726 0.112251 0.058 Uiso 1 1 calc R U . . .
C6 C 0.5324(3) 0.2882(6) 0.2884(5) 0.0399(12) Uani 1 1 d . . . . .
H6 H 0.491328 0.229917 0.298454 0.048 Uiso 1 1 calc R U . . .
C7 C 0.5499(3) 0.3866(6) 0.3826(5) 0.0315(10) Uani 1 1 d . . . . .
C8 C 0.5055(3) 0.4065(6) 0.5026(5) 0.0370(11) Uani 1 1 d . . . . .
H8A H 0.537566 0.402812 0.577769 0.044 Uiso 1 1 calc R U . . .
H8AB H 0.483628 0.502813 0.500411 0.044 Uiso 1 1 calc R U . . .
C9 C 0.3798(3) 0.3263(6) 0.4723(5) 0.0357(11) Uani 1 1 d . . . . .
C10 C 0.3622(3) 0.4192(7) 0.3715(6) 0.0424(13) Uani 1 1 d . . . . .
H10 H 0.397970 0.472435 0.328323 0.051 Uiso 1 1 calc R U . . .
C11 C 0.2897(3) 0.4311(8) 0.3365(6) 0.0521(15) Uani 1 1 d . . . . .
H11 H 0.276932 0.493262 0.268461 0.062 Uiso 1 1 calc R U . . .
C12 C 0.2376(3) 0.3561(8) 0.3974(7) 0.0553(15) Uani 1 1 d . . . . .
H12 H 0.189493 0.366566 0.370733 0.066 Uiso 1 1 calc R U . . .
C13 C 0.2540(3) 0.2628(7) 0.4996(6) 0.0472(13) Uani 1 1 d . . . . .
H13 H 0.217589 0.211350 0.542959 0.057 Uiso 1 1 calc R U . . .
C14 C 0.3254(3) 0.2490(6) 0.5344(5) 0.0375(12) Uani 1 1 d . . . . .
C15 C 0.4470(3) 0.2377(6) 0.6513(5) 0.0369(11) Uani 1 1 d . . . . .
H15 H 0.444944 0.317017 0.715338 0.044 Uiso 1 1 calc R U . . .
C16 C 0.5112(3) 0.1450(6) 0.6794(5) 0.0372(11) Uani 1 1 d . . . . .
C17 C 0.5428(3) 0.0587(7) 0.5873(6) 0.0473(14) Uani 1 1 d . . . . .
H17 H 0.523886 0.057663 0.503036 0.057 Uiso 1 1 calc R U . . .
C18 C 0.6015(3) -0.0260(7) 0.6161(6) 0.0541(15) Uani 1 1 d . . . . .
H18 H 0.623363 -0.081849 0.551087 0.065 Uiso 1 1 calc R U . . .
C19 C 0.6282(3) -0.0290(8) 0.7396(7) 0.0551(16) Uani 1 1 d . . . . .
H19 H 0.667800 -0.088136 0.759934 0.066 Uiso 1 1 calc R U . . .
C20 C 0.5969(3) 0.0545(9) 0.8332(7) 0.0611(17) Uani 1 1 d . . . . .
H20 H 0.615051 0.052643 0.917882 0.073 Uiso 1 1 calc R U . . .
C21 C 0.5387(3) 0.1415(7) 0.8039(6) 0.0480(14) Uani 1 1 d . . . . .
H21 H 0.517584 0.198686 0.868675 0.058 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 C14 1.764(6) . ?
S1 C15 1.838(5) . ?
S2 C2 1.773(7) . ?
S2 C1 1.790(7) . ?
N1 C9 1.392(6) . ?
N1 C8 1.451(6) . ?
N1 C15 1.479(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.383(9) . ?
C2 C7 1.407(7) . ?
C3 C4 1.398(10) . ?
C3 H3 0.9400 . ?
C4 C5 1.351(9) . ?
C4 H4 0.9400 . ?
C5 C6 1.417(7) . ?
C5 H5 0.9400 . ?
C6 C7 1.373(7) . ?
C6 H6 0.9400 . ?
C7 C8 1.503(7) . ?
C8 H8A 0.9800 . ?
C8 H8AB 0.9800 . ?
C9 C10 1.391(9) . ?
C9 C14 1.395(8) . ?
C10 C11 1.398(8) . ?
C10 H10 0.9400 . ?
C11 C12 1.347(10) . ?
C11 H11 0.9400 . ?
C12 C13 1.399(10) . ?
C12 H12 0.9400 . ?
C13 C14 1.379(7) . ?
C13 H13 0.9400 . ?
C15 C16 1.497(7) . ?
C15 H15 0.9900 . ?
C16 C17 1.375(8) . ?
C16 C21 1.386(8) . ?
C17 C18 1.376(9) . ?
C17 H17 0.9400 . ?
C18 C19 1.372(9) . ?
C18 H18 0.9400 . ?
C19 C20 1.369(10) . ?
C19 H19 0.9400 . ?
C20 C21 1.381(9) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?

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
C14 S1 C15 90.7(2) . . ?
C2 S2 C1 104.4(4) . . ?
C9 N1 C8 120.4(4) . . ?
C9 N1 C15 111.9(4) . . ?
C8 N1 C15 113.2(4) . . ?
S2 C1 H1A 109.5 . . ?
S2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 120.3(6) . . ?
C3 C2 S2 123.6(5) . . ?
C7 C2 S2 116.1(4) . . ?
C2 C3 C4 119.5(6) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 121.2(6) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.3(6) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 120.8(6) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 118.9(5) . . ?
C6 C7 C8 122.6(5) . . ?
C2 C7 C8 118.5(5) . . ?
N1 C8 C7 114.6(4) . . ?
N1 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
N1 C8 H8AB 108.6 . . ?
C7 C8 H8AB 108.6 . . ?
H8A C8 H8AB 107.6 . . ?
C10 C9 N1 126.0(5) . . ?
C10 C9 C14 119.5(5) . . ?
N1 C9 C14 114.5(5) . . ?
C9 C10 C11 118.0(6) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
C12 C11 C10 121.9(6) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 121.1(6) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 117.5(6) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?
C13 C14 C9 121.9(6) . . ?
C13 C14 S1 127.5(5) . . ?
C9 C14 S1 110.6(4) . . ?
N1 C15 C16 112.7(4) . . ?
N1 C15 S1 103.9(3) . . ?
C16 C15 S1 112.9(4) . . ?
N1 C15 H15 109.1 . . ?
C16 C15 H15 109.1 . . ?
S1 C15 H15 109.1 . . ?
C17 C16 C21 118.4(5) . . ?
C17 C16 C15 122.5(5) . . ?
C21 C16 C15 119.1(5) . . ?
C16 C17 C18 121.2(6) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 120.0(6) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 119.6(6) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.4(6) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.3(6) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 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
C1 S2 C2 C3 -12.5(6) . . . . ?
C1 S2 C2 C7 167.6(5) . . . . ?
C7 C2 C3 C4 -0.2(8) . . . . ?
S2 C2 C3 C4 179.9(4) . . . . ?
C2 C3 C4 C5 -0.3(9) . . . . ?
C3 C4 C5 C6 0.5(9) . . . . ?
C4 C5 C6 C7 -0.2(8) . . . . ?
C5 C6 C7 C2 -0.3(8) . . . . ?
C5 C6 C7 C8 179.6(5) . . . . ?
C3 C2 C7 C6 0.5(8) . . . . ?
S2 C2 C7 C6 -179.5(4) . . . . ?
C3 C2 C7 C8 -179.4(5) . . . . ?
S2 C2 C7 C8 0.5(6) . . . . ?
C9 N1 C8 C7 -91.7(6) . . . . ?
C15 N1 C8 C7 132.2(5) . . . . ?
C6 C7 C8 N1 8.2(7) . . . . ?
C2 C7 C8 N1 -171.8(4) . . . . ?
C8 N1 C9 C10 23.8(8) . . . . ?
C15 N1 C9 C10 160.5(6) . . . . ?
C8 N1 C9 C14 -156.5(5) . . . . ?
C15 N1 C9 C14 -19.8(6) . . . . ?
N1 C9 C10 C11 179.7(5) . . . . ?
C14 C9 C10 C11 0.0(8) . . . . ?
C9 C10 C11 C12 0.1(9) . . . . ?
C10 C11 C12 C13 0.3(10) . . . . ?
C11 C12 C13 C14 -0.9(9) . . . . ?
C12 C13 C14 C9 1.1(8) . . . . ?
C12 C13 C14 S1 -178.3(4) . . . . ?
C10 C9 C14 C13 -0.6(8) . . . . ?
N1 C9 C14 C13 179.7(5) . . . . ?
C10 C9 C14 S1 178.8(4) . . . . ?
N1 C9 C14 S1 -0.9(6) . . . . ?
C15 S1 C14 C13 -164.8(5) . . . . ?
C15 S1 C14 C9 15.8(4) . . . . ?
C9 N1 C15 C16 152.0(5) . . . . ?
C8 N1 C15 C16 -68.1(6) . . . . ?
C9 N1 C15 S1 29.4(5) . . . . ?
C8 N1 C15 S1 169.4(3) . . . . ?
C14 S1 C15 N1 -24.9(4) . . . . ?
C14 S1 C15 C16 -147.3(4) . . . . ?
N1 C15 C16 C17 -36.3(7) . . . . ?
S1 C15 C16 C17 81.1(6) . . . . ?
N1 C15 C16 C21 146.0(5) . . . . ?
S1 C15 C16 C21 -96.6(6) . . . . ?
C21 C16 C17 C18 -1.9(9) . . . . ?
C15 C16 C17 C18 -179.6(5) . . . . ?
C16 C17 C18 C19 2.1(10) . . . . ?
C17 C18 C19 C20 -1.1(11) . . . . ?
C18 C19 C20 C21 0.0(11) . . . . ?
C19 C20 C21 C16 0.2(11) . . . . ?
C17 C16 C21 C20 0.8(9) . . . . ?
C15 C16 C21 C20 178.6(6) . . . . ?

_refine_diff_density_max         0.581
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_S0733
_database_code_depnum_ccdc_archive 'CCDC 2081264'
loop_
_audit_author_name
_audit_author_address
'Jeffrey Ovens'
;University of Ottawa
Canada
;
_audit_update_record             
;
2021-04-30 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
#===============================================================================
# 5. CHEMICAL DATA

_chemical_name_systematic        
; 
;

_chemical_formula_sum            'C21 H28 B N O2 S2'
_chemical_formula_moiety         'C21 H28 B N O2 S2'
_chemical_formula_weight         401.37
#=============================================================
# 6. CRYSTAL DATA

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

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

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

#------------------------------------------------
_cell_length_a                   10.9771(4)
_cell_length_b                   11.5337(4)
_cell_length_c                   17.6262(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.4600(10)
_cell_angle_gamma                90
_cell_volume                     2160.90(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    5674
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      25.88

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.152
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_max          0.364

_exptl_crystal_density_diffrn    1.234
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7191
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS

#=============================================================================
# 7. EXPERIMENTAL DATA

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω and φ scans'
_diffrn_ambient_temperature      203(2)
_diffrn_reflns_number            16576
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.916
_diffrn_reflns_theta_max         26.422
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000


#==========================================================================
# 8. REFINEMENT DATA

_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_number_total             4421
_reflns_number_gt                3121
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_special_details          none

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details none
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         4421
_refine_ls_number_parameters     309
_refine_ls_number_restraints     202
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1454
_refine_ls_wR_factor_gt          0.1280
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0671P)²+1.0351P] where P=(Fo²+2Fc²)/3'

_refine_diff_density_max         0.563
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.056

#---------------------------------------------------------


#========================================================== 
# 9. General computing 

_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_cell_refinement       'Bruker SAINT'
_computing_structure_solution    
; 
 SHELXT 2014/5 (Sheldrick, 2014)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_shelx_SHELXL_version_number     2018/3

#===================================================================
# 10.  ATOMIC COORDINATES AND THERMAL PARAMETERS

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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'
B B 0.0013 0.0007 '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'
O O 0.0106 0.0060 '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'

#==============================================================================
# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

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 0.66468(6) 0.47637(6) 0.17952(4) 0.0361(2) Uani 1 1 d . . . . .
O1 O 0.94360(16) 0.34964(16) 0.27473(10) 0.0384(4) Uani 1 1 d . . . . .
N1 N 0.75581(18) 0.30457(17) 0.31991(11) 0.0265(4) Uani 1 1 d . . . . .
C2 C 0.7244(2) 0.2330(2) 0.44493(14) 0.0283(5) Uani 1 1 d D U . . .
C3 C 0.6589(2) 0.2367(2) 0.50319(14) 0.0317(6) Uani 1 1 d . . . . .
H3 H 0.681952 0.186799 0.546554 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5606(2) 0.3132(2) 0.49766(14) 0.0332(6) Uani 1 1 d . . . . .
H4 H 0.516574 0.314846 0.537060 0.040 Uiso 1 1 calc R U . . .
C5 C 0.5267(2) 0.3870(2) 0.43462(14) 0.0349(6) Uani 1 1 d . . . . .
H5 H 0.459701 0.439206 0.431020 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5912(2) 0.3844(2) 0.37648(14) 0.0317(6) Uani 1 1 d . . . . .
H6 H 0.567864 0.435246 0.333640 0.038 Uiso 1 1 calc R U . . .
C7 C 0.6897(2) 0.3077(2) 0.38066(13) 0.0262(5) Uani 1 1 d . . . . .
C8 C 0.6984(2) 0.2349(2) 0.25046(14) 0.0294(6) Uani 1 1 d . . . . .
H8A H 0.696858 0.153800 0.266770 0.035 Uiso 1 1 calc R U . . .
H8AB H 0.752792 0.239217 0.214090 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5675(2) 0.2687(2) 0.20687(13) 0.0304(6) Uani 1 1 d . . . . .
C10 C 0.4676(3) 0.1888(2) 0.20012(15) 0.0380(6) Uani 1 1 d . . . . .
H10 H 0.483642 0.116855 0.225712 0.046 Uiso 1 1 calc R U . . .
C11 C 0.3486(3) 0.2132(3) 0.15754(18) 0.0528(8) Uani 1 1 d . . . . .
H11 H 0.284564 0.157593 0.152612 0.063 Uiso 1 1 calc R U . . .
C12 C 0.3227(3) 0.3191(3) 0.12196(18) 0.0540(8) Uani 1 1 d . . . . .
H12 H 0.240481 0.335905 0.092863 0.065 Uiso 1 1 calc R U . . .
C13 C 0.4161(3) 0.4016(3) 0.12837(16) 0.0422(7) Uani 1 1 d . . . . .
H13 H 0.396661 0.474508 0.104605 0.051 Uiso 1 1 calc R U . . .
C14 C 0.5399(2) 0.3769(2) 0.17023(14) 0.0324(6) Uani 1 1 d . . . . .
C15 C 0.5992(3) 0.5898(3) 0.11202(18) 0.0541(8) Uani 1 1 d . . . . .
H15A H 0.567800 0.557260 0.060059 0.081 Uiso 1 1 calc R U . . .
H15B H 0.663751 0.646786 0.110982 0.081 Uiso 1 1 calc R U . . .
H15C H 0.530670 0.626674 0.128525 0.081 Uiso 1 1 calc R U . . .
C16 C 1.0452(3) 0.4341(3) 0.29675(17) 0.0522(6) Uani 1 1 d D . . . .
C17 C 0.9971(3) 0.5435(3) 0.2464(2) 0.0661(9) Uani 1 1 d . . . . .
H17A H 0.974408 0.522555 0.191397 0.099 Uiso 1 1 calc R U . . .
H17B H 1.062986 0.601708 0.255570 0.099 Uiso 1 1 calc R U . . .
H17C H 0.923961 0.574513 0.260976 0.099 Uiso 1 1 calc R U . . .
C18 C 1.1591(4) 0.3903(4) 0.2764(3) 0.0934(13) Uani 1 1 d . . . . .
H18A H 1.142365 0.380746 0.220065 0.140 Uiso 1 1 calc R U . . .
H18B H 1.182547 0.316185 0.301840 0.140 Uiso 1 1 calc R U . . .
H18C H 1.227272 0.445197 0.293896 0.140 Uiso 1 1 calc R U . . .
B1 B 0.8722(3) 0.3607(3) 0.32795(16) 0.0307(5) Uani 1 1 d D . . . .
O2A O 0.9121(7) 0.4480(7) 0.3860(4) 0.0311(12) Uani 0.488(16) 1 d D U P A 1
C1A C 0.8939(19) 0.0907(17) 0.5489(8) 0.054(3) Uani 0.46(3) 1 d D U P B 1
H1A1 H 0.905465 0.153979 0.586303 0.081 Uiso 0.46(3) 1 calc R U P B 1
H1A2 H 0.969702 0.044045 0.558867 0.081 Uiso 0.46(3) 1 calc R U P B 1
H1A3 H 0.823729 0.043016 0.554240 0.081 Uiso 0.46(3) 1 calc R U P B 1
S2A S 0.8619(12) 0.1484(12) 0.4514(7) 0.0424(18) Uani 0.46(3) 1 d D U P B 1
C19A C 1.0406(8) 0.4741(9) 0.3827(4) 0.0456(14) Uani 0.488(16) 1 d D . P A 1
C20A C 1.0627(12) 0.6030(11) 0.4033(7) 0.072(3) Uani 0.488(16) 1 d D . P A 1
H20A H 1.142664 0.626982 0.394263 0.107 Uiso 0.488(16) 1 calc R U P A 1
H20B H 1.063953 0.614902 0.457920 0.107 Uiso 0.488(16) 1 calc R U P A 1
H20C H 0.995524 0.648697 0.370571 0.107 Uiso 0.488(16) 1 calc R U P A 1
C21A C 1.1317(9) 0.4086(16) 0.4471(6) 0.088(4) Uani 0.488(16) 1 d D U P A 1
H21A H 1.131865 0.327358 0.433038 0.131 Uiso 0.488(16) 1 calc R U P A 1
H21B H 1.105927 0.416291 0.495674 0.131 Uiso 0.488(16) 1 calc R U P A 1
H21C H 1.215549 0.440358 0.453918 0.131 Uiso 0.488(16) 1 calc R U P A 1
O2B O 0.9352(7) 0.4185(8) 0.3920(4) 0.0312(14) Uani 0.512(16) 1 d D U P A 2
C1B C 0.8542(14) 0.0504(16) 0.5312(9) 0.056(3) Uani 0.54(3) 1 d D U P B 2
H1B1 H 0.867295 0.103704 0.575040 0.083 Uiso 0.54(3) 1 calc R U P B 2
H1B2 H 0.924266 -0.003269 0.539223 0.083 Uiso 0.54(3) 1 calc R U P B 2
H1B3 H 0.776814 0.007544 0.527212 0.083 Uiso 0.54(3) 1 calc R U P B 2
S2B S 0.8433(9) 0.1305(9) 0.4424(7) 0.0382(12) Uani 0.54(3) 1 d D U P B 2
C19B C 1.0615(8) 0.4427(9) 0.3841(4) 0.0474(14) Uani 0.512(16) 1 d D . P A 2
C20B C 1.1072(11) 0.5541(11) 0.4174(5) 0.064(3) Uani 0.512(16) 1 d D . P A 2
H20D H 1.189967 0.568522 0.409084 0.095 Uiso 0.512(16) 1 calc R U P A 2
H20E H 1.112491 0.553762 0.473192 0.095 Uiso 0.512(16) 1 calc R U P A 2
H20F H 1.049846 0.614643 0.392304 0.095 Uiso 0.512(16) 1 calc R U P A 2
C21B C 1.1370(9) 0.3442(11) 0.4307(6) 0.071(2) Uani 0.512(16) 1 d D U P A 2
H21D H 1.114500 0.271842 0.402736 0.107 Uiso 0.512(16) 1 calc R U P A 2
H21E H 1.118564 0.339174 0.481655 0.107 Uiso 0.512(16) 1 calc R U P A 2
H21F H 1.226077 0.358904 0.437499 0.107 Uiso 0.512(16) 1 calc R U P A 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 C14 1.763(3) . ?
S1 C15 1.793(3) . ?
O1 B1 1.370(3) . ?
O1 C16 1.459(3) . ?
N1 B1 1.408(3) . ?
N1 C7 1.436(3) . ?
N1 C8 1.468(3) . ?
C2 C3 1.394(3) . ?
C2 C7 1.399(3) . ?
C2 S2B 1.770(8) . ?
C2 S2A 1.776(9) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9400 . ?
C8 C9 1.502(3) . ?
C8 H8A 0.9800 . ?
C8 H8AB 0.9800 . ?
C9 C14 1.403(4) . ?
C9 C10 1.415(4) . ?
C10 C11 1.363(4) . ?
C10 H10 0.9400 . ?
C11 C12 1.370(5) . ?
C11 H11 0.9400 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.404(4) . ?
C13 H13 0.9400 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 C18 1.473(5) . ?
C16 C19B 1.509(7) . ?
C16 C17 1.557(5) . ?
C16 C19A 1.596(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
B1 O2B 1.344(6) . ?
B1 O2A 1.424(6) . ?
O2A C19A 1.457(7) . ?
C1A S2A 1.794(10) . ?
C1A H1A1 0.9700 . ?
C1A H1A2 0.9700 . ?
C1A H1A3 0.9700 . ?
C19A C21A 1.514(9) . ?
C19A C20A 1.536(10) . ?
C20A H20A 0.9700 . ?
C20A H20B 0.9700 . ?
C20A H20C 0.9700 . ?
C21A H21A 0.9700 . ?
C21A H21B 0.9700 . ?
C21A H21C 0.9700 . ?
O2B C19B 1.455(7) . ?
C1B S2B 1.796(9) . ?
C1B H1B1 0.9700 . ?
C1B H1B2 0.9700 . ?
C1B H1B3 0.9700 . ?
C19B C20B 1.449(9) . ?
C19B C21B 1.520(9) . ?
C20B H20D 0.9700 . ?
C20B H20E 0.9700 . ?
C20B H20F 0.9700 . ?
C21B H21D 0.9700 . ?
C21B H21E 0.9700 . ?
C21B H21F 0.9700 . ?

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
C14 S1 C15 103.87(14) . . ?
B1 O1 C16 106.6(2) . . ?
B1 N1 C7 121.9(2) . . ?
B1 N1 C8 121.7(2) . . ?
C7 N1 C8 116.36(19) . . ?
C3 C2 C7 119.4(2) . . ?
C3 C2 S2B 124.0(4) . . ?
C7 C2 S2B 116.4(4) . . ?
C3 C2 S2A 123.8(4) . . ?
C7 C2 S2A 116.5(4) . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C2 119.2(2) . . ?
C6 C7 N1 120.7(2) . . ?
C2 C7 N1 120.1(2) . . ?
N1 C8 C9 116.15(19) . . ?
N1 C8 H8A 108.2 . . ?
C9 C8 H8A 108.2 . . ?
N1 C8 H8AB 108.2 . . ?
C9 C8 H8AB 108.2 . . ?
H8A C8 H8AB 107.4 . . ?
C14 C9 C10 117.8(2) . . ?
C14 C9 C8 122.4(2) . . ?
C10 C9 C8 119.8(2) . . ?
C11 C10 C9 121.8(3) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 119.5(3) . . ?
C9 C14 S1 117.52(19) . . ?
C13 C14 S1 123.0(2) . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 C18 110.2(3) . . ?
O1 C16 C19B 101.7(4) . . ?
C18 C16 C19B 112.3(5) . . ?
O1 C16 C17 105.2(2) . . ?
C18 C16 C17 109.1(3) . . ?
C19B C16 C17 117.7(5) . . ?
O1 C16 C19A 104.0(4) . . ?
C18 C16 C19A 124.1(4) . . ?
C17 C16 C19A 102.7(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2B B1 O1 111.1(4) . . ?
O2B B1 N1 125.1(4) . . ?
O1 B1 N1 123.2(2) . . ?
O1 B1 O2A 115.6(4) . . ?
N1 B1 O2A 120.4(4) . . ?
B1 O2A C19A 104.1(5) . . ?
S2A C1A H1A1 109.5 . . ?
S2A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
S2A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
C2 S2A C1A 103.0(7) . . ?
O2A C19A C21A 109.3(7) . . ?
O2A C19A C20A 106.7(7) . . ?
C21A C19A C20A 105.6(8) . . ?
O2A C19A C16 103.8(6) . . ?
C21A C19A C16 113.3(7) . . ?
C20A C19A C16 117.6(7) . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C19A C21A H21A 109.5 . . ?
C19A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C19A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
B1 O2B C19B 108.5(5) . . ?
S2B C1B H1B1 109.5 . . ?
S2B C1B H1B2 109.5 . . ?
H1B1 C1B H1B2 109.5 . . ?
S2B C1B H1B3 109.5 . . ?
H1B1 C1B H1B3 109.5 . . ?
H1B2 C1B H1B3 109.5 . . ?
C2 S2B C1B 102.1(6) . . ?
C20B C19B O2B 112.0(6) . . ?
C20B C19B C16 114.3(7) . . ?
O2B C19B C16 102.2(6) . . ?
C20B C19B C21B 110.9(7) . . ?
O2B C19B C21B 102.1(6) . . ?
C16 C19B C21B 114.3(6) . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C19B C21B H21D 109.5 . . ?
C19B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C19B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 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
C7 C2 C3 C4 0.1(4) . . . . ?
S2B C2 C3 C4 -174.7(5) . . . . ?
S2A C2 C3 C4 173.4(7) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C5 C6 C7 C2 -0.5(4) . . . . ?
C5 C6 C7 N1 179.5(2) . . . . ?
C3 C2 C7 C6 0.3(4) . . . . ?
S2B C2 C7 C6 175.5(5) . . . . ?
S2A C2 C7 C6 -173.5(6) . . . . ?
C3 C2 C7 N1 -179.7(2) . . . . ?
S2B C2 C7 N1 -4.5(5) . . . . ?
S2A C2 C7 N1 6.5(7) . . . . ?
B1 N1 C7 C6 99.4(3) . . . . ?
C8 N1 C7 C6 -83.4(3) . . . . ?
B1 N1 C7 C2 -80.6(3) . . . . ?
C8 N1 C7 C2 96.6(3) . . . . ?
B1 N1 C8 C9 -124.2(3) . . . . ?
C7 N1 C8 C9 58.7(3) . . . . ?
N1 C8 C9 C14 63.3(3) . . . . ?
N1 C8 C9 C10 -118.3(2) . . . . ?
C14 C9 C10 C11 2.1(4) . . . . ?
C8 C9 C10 C11 -176.3(2) . . . . ?
C9 C10 C11 C12 -2.1(4) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C11 C12 C13 C14 1.4(4) . . . . ?
C10 C9 C14 C13 -0.4(3) . . . . ?
C8 C9 C14 C13 178.0(2) . . . . ?
C10 C9 C14 S1 179.55(18) . . . . ?
C8 C9 C14 S1 -2.1(3) . . . . ?
C12 C13 C14 C9 -1.3(4) . . . . ?
C12 C13 C14 S1 178.8(2) . . . . ?
C15 S1 C14 C9 170.12(19) . . . . ?
C15 S1 C14 C13 -10.0(3) . . . . ?
B1 O1 C16 C18 148.3(3) . . . . ?
B1 O1 C16 C19B 29.0(5) . . . . ?
B1 O1 C16 C17 -94.3(3) . . . . ?
B1 O1 C16 C19A 13.3(5) . . . . ?
C16 O1 B1 O2B -16.9(6) . . . . ?
C16 O1 B1 N1 171.1(3) . . . . ?
C16 O1 B1 O2A 1.2(5) . . . . ?
C7 N1 B1 O2B 2.3(7) . . . . ?
C8 N1 B1 O2B -174.7(6) . . . . ?
C7 N1 B1 O1 173.1(2) . . . . ?
C8 N1 B1 O1 -3.8(4) . . . . ?
C7 N1 B1 O2A -17.4(6) . . . . ?
C8 N1 B1 O2A 165.6(5) . . . . ?
O1 B1 O2A C19A -16.6(7) . . . . ?
N1 B1 O2A C19A 173.2(4) . . . . ?
C3 C2 S2A C1A -5.6(8) . . . . ?
C7 C2 S2A C1A 167.9(6) . . . . ?
B1 O2A C19A C21A -98.3(8) . . . . ?
B1 O2A C19A C20A 147.8(7) . . . . ?
B1 O2A C19A C16 22.9(7) . . . . ?
O1 C16 C19A O2A -22.8(6) . . . . ?
C18 C16 C19A O2A -149.6(5) . . . . ?
C17 C16 C19A O2A 86.6(6) . . . . ?
O1 C16 C19A C21A 95.7(8) . . . . ?
C18 C16 C19A C21A -31.0(9) . . . . ?
C17 C16 C19A C21A -154.9(7) . . . . ?
O1 C16 C19A C20A -140.4(7) . . . . ?
C18 C16 C19A C20A 92.8(8) . . . . ?
C17 C16 C19A C20A -31.0(7) . . . . ?
O1 B1 O2B C19B -3.6(7) . . . . ?
N1 B1 O2B C19B 168.2(5) . . . . ?
C3 C2 S2B C1B -2.8(7) . . . . ?
C7 C2 S2B C1B -177.7(6) . . . . ?
B1 O2B C19B C20B 144.3(7) . . . . ?
B1 O2B C19B C16 21.5(7) . . . . ?
B1 O2B C19B C21B -97.0(7) . . . . ?
O1 C16 C19B C20B -151.1(6) . . . . ?
C18 C16 C19B C20B 91.1(7) . . . . ?
C17 C16 C19B C20B -36.8(8) . . . . ?
O1 C16 C19B O2B -29.9(6) . . . . ?
C18 C16 C19B O2B -147.7(5) . . . . ?
C17 C16 C19B O2B 84.4(6) . . . . ?
O1 C16 C19B C21B 79.6(6) . . . . ?
C18 C16 C19B C21B -38.2(7) . . . . ?
C17 C16 C19B C21B -166.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1A H1A2 S2A 0.97 2.92 3.848(16) 159.7 3_756 yes
C21A H21B O2A 0.97 2.65 3.510(19) 147.4 3_766 yes
C1B H1B2 S2B 0.97 2.89 3.850(14) 170.4 3_756 yes
C20B H20E O2B 0.97 2.58 3.518(11) 163.6 3_766 yes

