# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2110386'
loop_
_audit_author_name
_audit_author_address
'Andrej Pevec'
;Faculty of Chemistry and Chemical Technology, University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H20 B Cu F4 N7 O2 S'
_chemical_formula_weight         464.75

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'
F F 0.0171 0.0103 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.0033(3)
_cell_length_b                   10.8941(3)
_cell_length_c                   25.6059(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.242(4)
_cell_angle_gamma                90
_cell_volume                     1938.01(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8107
_cell_measurement_theta_min      3.4380
_cell_measurement_theta_max      30.1670

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.293
_shelx_estimated_absorpt_T_min   0.511
_shelx_estimated_absorpt_T_max   0.782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51975
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlis PRO; Oxford Diffraction, 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            17559
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.941
_diffrn_reflns_theta_max         27.485
_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             4425
_reflns_number_gt                3789
_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       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.9688P] 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         4425
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0001

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
Cu1 Cu 0.20037(5) 0.46833(3) 0.04197(2) 0.04201(12) Uani 1 1 d . . . . .
S1 S 0.23718(11) 0.06752(6) 0.02448(4) 0.0611(2) Uani 1 1 d . . . . .
O1 O 0.1064(3) 0.59420(15) 0.08771(7) 0.0440(4) Uani 1 1 d . . . . .
N1 N 0.2427(3) 0.2985(2) 0.01110(9) 0.0450(5) Uani 1 1 d . . . . .
N2 N 0.1327(3) 0.36770(17) 0.09879(8) 0.0381(4) Uani 1 1 d . . . . .
N3 N 0.0780(3) 0.42658(18) 0.14212(8) 0.0415(4) Uani 1 1 d . . . . .
N4 N 0.1596(3) 0.72306(18) 0.19065(9) 0.0466(5) Uani 1 1 d . . . . .
N5 N 0.2435(4) 0.5720(2) -0.01614(9) 0.0520(6) Uani 1 1 d . . . . .
N6 N 0.2422(3) 0.6828(2) -0.01303(9) 0.0459(5) Uani 1 1 d . . . . .
N7 N 0.2394(4) 0.7866(2) -0.01306(13) 0.0704(8) Uani 1 1 d . . . . .
C1 C 0.2945(4) 0.2480(3) -0.03385(11) 0.0565(7) Uani 1 1 d . . . . .
H1 H 0.324219 0.294457 -0.062203 0.068 Uiso 1 1 calc R U . . .
C2 C 0.2986(4) 0.1226(3) -0.03316(13) 0.0657(9) Uani 1 1 d . . . . .
H2 H 0.330772 0.073994 -0.060596 0.079 Uiso 1 1 calc R U . . .
C3 C 0.2066(3) 0.2139(2) 0.04513(11) 0.0444(6) Uani 1 1 d . . . . .
C4 C 0.1393(3) 0.2490(2) 0.09495(10) 0.0411(5) Uani 1 1 d . . . . .
C5 C 0.0840(5) 0.1594(3) 0.13387(14) 0.0630(8) Uani 1 1 d . . . . .
H5A H 0.028762 0.202194 0.161124 0.095 Uiso 1 1 calc R U . . .
H5B H 0.195997 0.115182 0.149030 0.095 Uiso 1 1 calc R U . . .
H5C H -0.008611 0.102910 0.116695 0.095 Uiso 1 1 calc R U . . .
C6 C 0.0709(3) 0.5449(2) 0.13063(10) 0.0392(5) Uani 1 1 d . . . . .
C7 C 0.0108(4) 0.6261(2) 0.17310(10) 0.0451(6) Uani 1 1 d . . . . .
H7A H -0.010638 0.575999 0.203124 0.054 Uiso 1 1 calc R U . . .
H7B H -0.109846 0.665899 0.160175 0.054 Uiso 1 1 calc R U . . .
C8 C 0.3542(4) 0.6660(3) 0.20328(15) 0.0667(9) Uani 1 1 d . . . . .
H8A H 0.396023 0.634299 0.171627 0.100 Uiso 1 1 calc R U . . .
H8B H 0.347547 0.600326 0.227976 0.100 Uiso 1 1 calc R U . . .
H8C H 0.444058 0.726783 0.218341 0.100 Uiso 1 1 calc R U . . .
C9 C 0.1624(5) 0.8209(3) 0.14928(14) 0.0659(8) Uani 1 1 d . . . . .
H9A H 0.253555 0.883307 0.161827 0.099 Uiso 1 1 calc R U . . .
H9B H 0.036645 0.856615 0.141870 0.099 Uiso 1 1 calc R U . . .
H9C H 0.198896 0.785076 0.117732 0.099 Uiso 1 1 calc R U . . .
C10 C 0.1041(6) 0.7822(3) 0.23965(13) 0.0689(9) Uani 1 1 d . . . . .
H10A H 0.200962 0.840475 0.252941 0.103 Uiso 1 1 calc R U . . .
H10B H 0.092909 0.720301 0.265788 0.103 Uiso 1 1 calc R U . . .
H10C H -0.017130 0.823448 0.231481 0.103 Uiso 1 1 calc R U . . .
O2 O 0.5288(3) 0.4835(2) 0.09579(10) 0.0655(6) Uani 1 1 d . . . . .
H2A H 0.597717 0.476524 0.072345 0.098 Uiso 1 1 calc R U . . .
C11 C 0.5868(5) 0.3947(4) 0.13691(16) 0.0807(11) Uani 1 1 d . . . . .
H11A H 0.704960 0.420925 0.156912 0.121 Uiso 1 1 calc R U . . .
H11B H 0.605428 0.316172 0.121344 0.121 Uiso 1 1 calc R U . . .
H11C H 0.488454 0.388344 0.159715 0.121 Uiso 1 1 calc R U . . .
B1 B 0.6482(6) 0.9975(4) 0.18740(18) 0.0661(9) Uani 1 1 d . . . . .
F1A F 0.4859(10) 0.9962(10) 0.2109(4) 0.089(3) Uani 0.59(2) 1 d . . P A 1
F2A F 0.6829(13) 0.8756(8) 0.1707(5) 0.104(3) Uani 0.59(2) 1 d . . P A 1
F3A F 0.6041(18) 1.0611(10) 0.1409(3) 0.120(3) Uani 0.59(2) 1 d . . P A 1
F4A F 0.8087(18) 1.0302(11) 0.2167(6) 0.113(3) Uani 0.59(2) 1 d . . P A 1
F1B F 0.542(4) 0.954(3) 0.2247(9) 0.170(9) Uani 0.41(2) 1 d . . P A 2
F2B F 0.697(3) 0.913(2) 0.1595(7) 0.151(7) Uani 0.41(2) 1 d . . P A 2
F3B F 0.556(4) 1.0791(19) 0.1603(14) 0.212(11) Uani 0.41(2) 1 d . . P A 2
F4B F 0.785(3) 1.071(2) 0.2166(7) 0.123(7) Uani 0.41(2) 1 d . . 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
Cu1 N5 1.922(2) . ?
Cu1 N2 1.928(2) . ?
Cu1 O1 1.9694(17) . ?
Cu1 N1 2.048(2) . ?
S1 C2 1.698(4) . ?
S1 C3 1.702(2) . ?
O1 C6 1.276(3) . ?
N1 C3 1.315(4) . ?
N1 C1 1.366(4) . ?
N2 C4 1.298(3) . ?
N2 N3 1.377(3) . ?
N3 C6 1.321(3) . ?
N4 C8 1.496(4) . ?
N4 C9 1.504(4) . ?
N4 C10 1.504(4) . ?
N4 C7 1.512(3) . ?
N5 N6 1.209(3) . ?
N6 N7 1.131(3) . ?
C1 C2 1.366(5) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.465(4) . ?
C4 C5 1.481(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.503(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O2 C11 1.449(4) . ?
O2 H2A 0.8200 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
B1 F2B 1.241(15) . ?
B1 F3B 1.256(17) . ?
B1 F4A 1.320(14) . ?
B1 F1A 1.351(9) . ?
B1 F1B 1.368(16) . ?
B1 F3A 1.379(10) . ?
B1 F4B 1.389(19) . ?
B1 F2A 1.425(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Cu1 N2 174.81(10) . . ?
N5 Cu1 O1 98.51(9) . . ?
N2 Cu1 O1 79.33(8) . . ?
N5 Cu1 N1 100.81(9) . . ?
N2 Cu1 N1 80.73(9) . . ?
O1 Cu1 N1 159.05(9) . . ?
C2 S1 C3 89.68(15) . . ?
C6 O1 Cu1 109.59(15) . . ?
C3 N1 C1 111.7(2) . . ?
C3 N1 Cu1 109.16(17) . . ?
C1 N1 Cu1 139.1(2) . . ?
C4 N2 N3 122.8(2) . . ?
C4 N2 Cu1 119.65(18) . . ?
N3 N2 Cu1 117.57(14) . . ?
C6 N3 N2 106.36(19) . . ?
C8 N4 C9 110.7(3) . . ?
C8 N4 C10 108.8(2) . . ?
C9 N4 C10 108.2(2) . . ?
C8 N4 C7 110.4(2) . . ?
C9 N4 C7 110.8(2) . . ?
C10 N4 C7 107.8(2) . . ?
N6 N5 Cu1 122.15(19) . . ?
N7 N6 N5 176.2(3) . . ?
N1 C1 C2 113.6(3) . . ?
N1 C1 H1 123.2 . . ?
C2 C1 H1 123.2 . . ?
C1 C2 S1 110.9(2) . . ?
C1 C2 H2 124.5 . . ?
S1 C2 H2 124.5 . . ?
N1 C3 C4 120.3(2) . . ?
N1 C3 S1 114.1(2) . . ?
C4 C3 S1 125.6(2) . . ?
N2 C4 C3 110.1(2) . . ?
N2 C4 C5 126.2(2) . . ?
C3 C4 C5 123.7(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O1 C6 N3 126.6(2) . . ?
O1 C6 C7 118.6(2) . . ?
N3 C6 C7 114.8(2) . . ?
C6 C7 N4 112.4(2) . . ?
C6 C7 H7A 109.1 . . ?
N4 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
N4 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 O2 H2A 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F2B B1 F3B 111.6(15) . . ?
F4A B1 F1A 117.0(8) . . ?
F2B B1 F1B 111.1(12) . . ?
F3B B1 F1B 110.2(13) . . ?
F4A B1 F3A 115.9(8) . . ?
F1A B1 F3A 106.2(7) . . ?
F2B B1 F4B 120.9(12) . . ?
F3B B1 F4B 99.3(18) . . ?
F1B B1 F4B 102.9(10) . . ?
F4A B1 F2A 104.9(7) . . ?
F1A B1 F2A 108.0(6) . . ?
F3A B1 F2A 103.7(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N2 N3 C6 -174.4(2) . . . . ?
Cu1 N2 N3 C6 5.3(2) . . . . ?
C3 N1 C1 C2 -0.5(3) . . . . ?
Cu1 N1 C1 C2 -179.6(2) . . . . ?
N1 C1 C2 S1 -0.1(3) . . . . ?
C3 S1 C2 C1 0.5(2) . . . . ?
C1 N1 C3 C4 -177.0(2) . . . . ?
Cu1 N1 C3 C4 2.4(3) . . . . ?
C1 N1 C3 S1 0.8(3) . . . . ?
Cu1 N1 C3 S1 -179.76(11) . . . . ?
C2 S1 C3 N1 -0.8(2) . . . . ?
C2 S1 C3 C4 176.9(2) . . . . ?
N3 N2 C4 C3 -178.7(2) . . . . ?
Cu1 N2 C4 C3 1.6(3) . . . . ?
N3 N2 C4 C5 2.6(4) . . . . ?
Cu1 N2 C4 C5 -177.2(2) . . . . ?
N1 C3 C4 N2 -2.7(3) . . . . ?
S1 C3 C4 N2 179.73(18) . . . . ?
N1 C3 C4 C5 176.1(3) . . . . ?
S1 C3 C4 C5 -1.5(4) . . . . ?
Cu1 O1 C6 N3 -5.6(3) . . . . ?
Cu1 O1 C6 C7 175.65(17) . . . . ?
N2 N3 C6 O1 0.4(3) . . . . ?
N2 N3 C6 C7 179.3(2) . . . . ?
O1 C6 C7 N4 -58.6(3) . . . . ?
N3 C6 C7 N4 122.4(2) . . . . ?
C8 N4 C7 C6 -50.4(3) . . . . ?
C9 N4 C7 C6 72.7(3) . . . . ?
C10 N4 C7 C6 -169.1(2) . . . . ?

_refine_diff_density_max         0.479
_refine_diff_density_min         -0.335
_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_2
_database_code_depnum_ccdc_archive 'CCDC 2110387'
loop_
_audit_author_name
_audit_author_address
'Andrej Pevec'
;Faculty of Chemistry and Chemical Technology, University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H40 Mn2 N20 O4 S2'
_chemical_formula_weight         822.74

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'
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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.6427(5)
_cell_length_b                   10.8396(5)
_cell_length_c                   10.8617(8)
_cell_angle_alpha                106.971(5)
_cell_angle_beta                 103.497(5)
_cell_angle_gamma                112.469(5)
_cell_volume                     923.85(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3492
_cell_measurement_theta_min      3.5850
_cell_measurement_theta_max      27.5040

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_F_000             426
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.856
_shelx_estimated_absorpt_T_min   0.726
_shelx_estimated_absorpt_T_max   0.848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77987
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlis PRO; Oxford Diffraction, 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            10077
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4144
_reflns_number_gt                3319
_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       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²+0.2411P] 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         4144
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.0001

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
Mn1 Mn 0.42864(4) 0.60535(3) 0.42869(3) 0.03733(12) Uani 1 1 d . . . . .
S1 S 0.83045(8) 1.04019(7) 0.44293(7) 0.05410(18) Uani 1 1 d . . . . .
N1 N 0.6182(2) 0.7779(2) 0.3780(2) 0.0478(5) Uani 1 1 d . . . . .
N2 N 0.5135(2) 0.83705(19) 0.57952(18) 0.0384(4) Uani 1 1 d . . . . .
N3 N 0.4487(2) 0.8520(2) 0.68155(19) 0.0413(4) Uani 1 1 d . . . . .
N4 N 0.2191(2) 0.6157(2) 0.8008(2) 0.0446(4) Uani 1 1 d . . . . .
N5 N 0.6422(2) 0.6205(2) 0.5799(3) 0.0602(6) Uani 1 1 d . . . . .
N6 N 0.7802(2) 0.7161(2) 0.6285(2) 0.0510(5) Uani 1 1 d . . . . .
N7 N 0.9122(3) 0.8083(3) 0.6760(3) 0.0769(7) Uani 1 1 d . . . . .
N8 N 0.2679(3) 0.5171(3) 0.2187(3) 0.0750(7) Uani 1 1 d . . . . .
N9 N 0.2527(3) 0.4441(3) 0.1081(3) 0.0600(6) Uani 1 1 d . . . . .
N10 N 0.2309(6) 0.3740(4) -0.0039(4) 0.1230(13) Uani 1 1 d . . . . .
O1 O 0.25799(18) 0.60949(17) 0.52980(17) 0.0518(4) Uani 1 1 d . . . . .
C1 C 0.6813(3) 0.7727(3) 0.2770(3) 0.0550(6) Uani 1 1 d . . . . .
H1 H 0.646437 0.685206 0.200929 0.066 Uiso 1 1 calc R U . . .
C2 C 0.7971(3) 0.9031(3) 0.2958(3) 0.0591(7) Uani 1 1 d . . . . .
H2 H 0.851305 0.916324 0.236380 0.071 Uiso 1 1 calc R U . . .
C3 C 0.6854(3) 0.9142(2) 0.4724(2) 0.0415(5) Uani 1 1 d . . . . .
C4 C 0.6330(3) 0.9509(2) 0.5877(2) 0.0408(5) Uani 1 1 d . . . . .
C5 C 0.7123(3) 1.1059(3) 0.6958(3) 0.0575(6) Uani 1 1 d . . . . .
H5A H 0.644576 1.114892 0.746296 0.086 Uiso 1 1 calc R U . . .
H5B H 0.726645 1.171625 0.651006 0.086 Uiso 1 1 calc R U . . .
H5C H 0.816562 1.130734 0.759456 0.086 Uiso 1 1 calc R U . . .
C6 C 0.3162(3) 0.7245(2) 0.6409(2) 0.0406(5) Uani 1 1 d . . . . .
C7 C 0.2277(3) 0.7252(3) 0.7381(3) 0.0473(5) Uani 1 1 d . . . . .
H7A H 0.117740 0.702931 0.687251 0.057 Uiso 1 1 calc R U . . .
H7B H 0.282171 0.823405 0.813283 0.057 Uiso 1 1 calc R U . . .
C8 C 0.3866(3) 0.6409(3) 0.8705(3) 0.0645(7) Uani 1 1 d . . . . .
H8A H 0.454202 0.741356 0.938912 0.097 Uiso 1 1 calc R U . . .
H8B H 0.431940 0.621613 0.801820 0.097 Uiso 1 1 calc R U . . .
H8C H 0.381439 0.576033 0.915463 0.097 Uiso 1 1 calc R U . . .
C9 C 0.1461(4) 0.6408(4) 0.9070(3) 0.0745(8) Uani 1 1 d . . . . .
H9A H 0.139055 0.572582 0.948364 0.112 Uiso 1 1 calc R U . . .
H9B H 0.038993 0.625950 0.862467 0.112 Uiso 1 1 calc R U . . .
H9C H 0.213539 0.739794 0.978432 0.112 Uiso 1 1 calc R U . . .
C10 C 0.1145(3) 0.4593(3) 0.6940(3) 0.0659(7) Uani 1 1 d . . . . .
H10A H 0.161143 0.440009 0.626310 0.099 Uiso 1 1 calc R U . . .
H10B H 0.007093 0.442984 0.647914 0.099 Uiso 1 1 calc R U . . .
H10C H 0.108294 0.394356 0.739087 0.099 Uiso 1 1 calc R U . . .
O2 O 0.6656(2) 0.9972(2) 0.96621(19) 0.0684(5) Uani 1 1 d . . . . .
H2A H 0.599187 0.965184 0.886772 0.103 Uiso 1 1 calc R U . . .
C11 C 0.7929(4) 0.9650(4) 0.9597(3) 0.0796(9) Uani 1 1 d . . . . .
H11A H 0.834771 0.997288 0.896379 0.119 Uiso 1 1 calc R U . . .
H11B H 0.752100 0.860560 0.927313 0.119 Uiso 1 1 calc R U . . .
H11C H 0.878528 1.015013 1.051097 0.119 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
Mn1 N8 2.112(2) . ?
Mn1 O1 2.1879(16) . ?
Mn1 N5 2.229(2) . ?
Mn1 N5 2.2425(19) 2_666 ?
Mn1 N2 2.2500(18) . ?
Mn1 N1 2.3668(19) . ?
S1 C2 1.695(3) . ?
S1 C3 1.711(2) . ?
N1 C3 1.314(3) . ?
N1 C1 1.370(3) . ?
N2 C4 1.288(3) . ?
N2 N3 1.393(2) . ?
N3 C6 1.330(3) . ?
N4 C8 1.493(3) . ?
N4 C10 1.496(3) . ?
N4 C9 1.498(3) . ?
N4 C7 1.517(3) . ?
N5 N6 1.193(3) . ?
N6 N7 1.142(3) . ?
N8 N9 1.169(3) . ?
N9 N10 1.149(4) . ?
O1 C6 1.264(3) . ?
C1 C2 1.343(4) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.463(3) . ?
C4 C5 1.494(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.504(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O2 C11 1.410(3) . ?
O2 H2A 0.8200 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
N8 Mn1 O1 98.88(9) . . ?
N8 Mn1 N5 147.86(10) . . ?
O1 Mn1 N5 107.66(8) . . ?
N8 Mn1 N5 91.69(9) . 2_666 ?
O1 Mn1 N5 86.40(8) . 2_666 ?
N5 Mn1 N5 72.63(8) . 2_666 ?
N8 Mn1 N2 121.21(9) . . ?
O1 Mn1 N2 69.51(6) . . ?
N5 Mn1 N2 85.67(7) . . ?
N5 Mn1 N2 141.02(8) 2_666 . ?
N8 Mn1 N1 86.84(9) . . ?
O1 Mn1 N1 134.91(7) . . ?
N5 Mn1 N1 87.04(7) . . ?
N5 Mn1 N1 138.40(8) 2_666 . ?
N2 Mn1 N1 69.46(7) . . ?
C2 S1 C3 89.80(12) . . ?
C3 N1 C1 110.6(2) . . ?
C3 N1 Mn1 112.91(15) . . ?
C1 N1 Mn1 136.46(17) . . ?
C4 N2 N3 119.62(19) . . ?
C4 N2 Mn1 123.11(15) . . ?
N3 N2 Mn1 116.45(13) . . ?
C6 N3 N2 107.91(17) . . ?
C8 N4 C10 109.2(2) . . ?
C8 N4 C9 109.5(2) . . ?
C10 N4 C9 108.1(2) . . ?
C8 N4 C7 109.71(18) . . ?
C10 N4 C7 112.51(19) . . ?
C9 N4 C7 107.74(19) . . ?
N6 N5 Mn1 126.85(16) . . ?
N6 N5 Mn1 123.06(15) . 2_666 ?
Mn1 N5 Mn1 107.37(8) . 2_666 ?
N7 N6 N5 179.4(3) . . ?
N9 N8 Mn1 137.7(2) . . ?
N10 N9 N8 176.0(3) . . ?
C6 O1 Mn1 114.29(13) . . ?
C2 C1 N1 115.2(2) . . ?
C2 C1 H1 122.4 . . ?
N1 C1 H1 122.4 . . ?
C1 C2 S1 110.5(2) . . ?
C1 C2 H2 124.7 . . ?
S1 C2 H2 124.7 . . ?
N1 C3 C4 121.47(19) . . ?
N1 C3 S1 113.89(17) . . ?
C4 C3 S1 124.60(17) . . ?
N2 C4 C3 111.95(19) . . ?
N2 C4 C5 127.1(2) . . ?
C3 C4 C5 121.0(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O1 C6 N3 126.6(2) . . ?
O1 C6 C7 119.1(2) . . ?
N3 C6 C7 114.2(2) . . ?
C6 C7 N4 113.61(17) . . ?
C6 C7 H7A 108.8 . . ?
N4 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
N4 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 O2 H2A 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
C4 N2 N3 C6 172.62(18) . . . . ?
Mn1 N2 N3 C6 -17.36(19) . . . . ?
C3 N1 C1 C2 1.1(3) . . . . ?
Mn1 N1 C1 C2 -176.22(17) . . . . ?
N1 C1 C2 S1 -0.6(3) . . . . ?
C3 S1 C2 C1 0.0(2) . . . . ?
C1 N1 C3 C4 176.7(2) . . . . ?
Mn1 N1 C3 C4 -5.4(3) . . . . ?
C1 N1 C3 S1 -1.1(2) . . . . ?
Mn1 N1 C3 S1 176.92(9) . . . . ?
C2 S1 C3 N1 0.64(18) . . . . ?
C2 S1 C3 C4 -177.0(2) . . . . ?
N3 N2 C4 C3 179.66(16) . . . . ?
Mn1 N2 C4 C3 10.3(2) . . . . ?
N3 N2 C4 C5 -2.0(3) . . . . ?
Mn1 N2 C4 C5 -171.33(17) . . . . ?
N1 C3 C4 N2 -2.5(3) . . . . ?
S1 C3 C4 N2 174.93(16) . . . . ?
N1 C3 C4 C5 179.0(2) . . . . ?
S1 C3 C4 C5 -3.5(3) . . . . ?
Mn1 O1 C6 N3 17.6(3) . . . . ?
Mn1 O1 C6 C7 -165.04(15) . . . . ?
N2 N3 C6 O1 0.0(3) . . . . ?
N2 N3 C6 C7 -177.51(17) . . . . ?
O1 C6 C7 N4 63.7(3) . . . . ?
N3 C6 C7 N4 -118.6(2) . . . . ?
C8 N4 C7 C6 54.3(3) . . . . ?
C10 N4 C7 C6 -67.5(3) . . . . ?
C9 N4 C7 C6 173.4(2) . . . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2110388'
loop_
_audit_author_name
_audit_author_address
'Andrej Pevec'
;Faculty of Chemistry and Chemical Technology, University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT230_3                   
;
PROBLEM: Hirshfeld Test Diff for    N8       --N9       .       25.7 s.u.  
RESPONSE: The anomalous data for Hirshfeld test is an artefact in the structure.
According to other characterizations there is no doubt that azide ligand, 
three connected N atoms, is coordinated to Zn.
;
_vrf_PLAT242_3                   
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         N9 Check 
RESPONSE: The azide ligand is terminal group, false alarm occurs.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 N10 O S Zn'
_chemical_formula_weight         389.76

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

_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                   13.0826(10)
_cell_length_b                   10.2506(7)
_cell_length_c                   13.1685(13)
_cell_angle_alpha                90
_cell_angle_beta                 111.237(10)
_cell_angle_gamma                90
_cell_volume                     1646.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3220
_cell_measurement_theta_min      3.2910
_cell_measurement_theta_max      25.7050

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.639
_shelx_estimated_absorpt_T_min   0.440
_shelx_estimated_absorpt_T_max   0.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.54625
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlis PRO; Oxford Diffraction, 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            13910
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.589
_diffrn_reflns_theta_max         27.479
_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
_reflns_number_total             3779
_reflns_number_gt                2489
_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       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²+1.8652P] 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         3779
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1230
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0001

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 0.29408(4) 0.80305(5) 0.03169(4) 0.06880(19) Uani 1 1 d . . . . .
S1 S 0.56672(9) 0.78151(15) -0.10538(12) 0.0892(4) Uani 1 1 d . . . . .
N1 N 0.4500(3) 0.7567(4) 0.0104(3) 0.0730(10) Uani 1 1 d . . . . .
N2 N 0.2930(2) 0.9226(3) -0.0948(3) 0.0552(7) Uani 1 1 d . . . . .
N3 N 0.2060(2) 1.0053(3) -0.1434(3) 0.0568(8) Uani 1 1 d . . . . .
N4 N 0.0418(2) 1.2113(3) -0.1266(2) 0.0469(7) Uani 1 1 d . . . . .
N5 N 0.3430(3) 0.8671(5) 0.1825(3) 0.0941(13) Uani 1 1 d . . . . .
N6 N 0.2990(3) 0.9516(5) 0.2089(3) 0.0895(13) Uani 1 1 d . . . . .
N7 N 0.2573(4) 1.0369(6) 0.2368(5) 0.146(2) Uani 1 1 d . . . . .
N8 N 0.2337(5) 0.6197(5) 0.0097(5) 0.1011(16) Uani 1 1 d . . . . .
N9 N 0.1652(3) 0.6008(3) -0.0354(3) 0.0490(8) Uani 1 1 d . . . . .
N10 N 0.0688(5) 0.5759(4) -0.0808(4) 0.1187(17) Uani 1 1 d . . . . .
O1 O 0.1335(2) 0.9070(3) -0.0265(2) 0.0643(7) Uani 1 1 d . . . . .
C1 C 0.5338(4) 0.6677(5) 0.0482(5) 0.0909(15) Uani 1 1 d . . . . .
H1 H 0.541689 0.612229 0.106471 0.109 Uiso 1 1 calc R U . . .
C2 C 0.6032(4) 0.6673(5) -0.0057(5) 0.0942(17) Uani 1 1 d . . . . .
H2 H 0.663200 0.611849 0.009475 0.113 Uiso 1 1 calc R U . . .
C3 C 0.4570(3) 0.8237(4) -0.0720(3) 0.0603(10) Uani 1 1 d . . . . .
C4 C 0.3741(3) 0.9200(4) -0.1303(3) 0.0580(9) Uani 1 1 d . . . . .
C5 C 0.3822(4) 1.0011(5) -0.2197(4) 0.0837(14) Uani 1 1 d . . . . .
H5A H 0.343694 1.081658 -0.223152 0.126 Uiso 1 1 calc R U . . .
H5B H 0.350222 0.955222 -0.287504 0.126 Uiso 1 1 calc R U . . .
H5C H 0.457900 1.019017 -0.206757 0.126 Uiso 1 1 calc R U . . .
C6 C 0.1316(3) 0.9863(3) -0.0986(3) 0.0470(8) Uani 1 1 d . . . . .
C7 C 0.0275(3) 1.0676(3) -0.1477(3) 0.0536(9) Uani 1 1 d . . . . .
H7A H -0.001716 1.053591 -0.225902 0.064 Uiso 1 1 calc R U . . .
H7B H -0.026581 1.035924 -0.119110 0.064 Uiso 1 1 calc R U . . .
C8 C 0.0976(3) 1.2365(4) -0.0073(3) 0.0616(10) Uani 1 1 d . . . . .
H8A H 0.056795 1.195740 0.031725 0.092 Uiso 1 1 calc R U . . .
H8B H 0.101301 1.328774 0.005909 0.092 Uiso 1 1 calc R U . . .
H8C H 0.170432 1.201037 0.017102 0.092 Uiso 1 1 calc R U . . .
C9 C 0.1054(4) 1.2737(4) -0.1885(4) 0.0682(11) Uani 1 1 d . . . . .
H9A H 0.176010 1.232817 -0.168583 0.102 Uiso 1 1 calc R U . . .
H9B H 0.114760 1.364926 -0.171129 0.102 Uiso 1 1 calc R U . . .
H9C H 0.066159 1.263183 -0.265263 0.102 Uiso 1 1 calc R U . . .
C10 C -0.0711(3) 1.2711(4) -0.1645(3) 0.0646(10) Uani 1 1 d . . . . .
H10A H -0.109294 1.250433 -0.239875 0.097 Uiso 1 1 calc R U . . .
H10B H -0.064822 1.364062 -0.155660 0.097 Uiso 1 1 calc R U . . .
H10C H -0.110948 1.236807 -0.121907 0.097 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 N5 1.965(4) . ?
Zn1 N8 2.019(6) . ?
Zn1 N2 2.064(3) . ?
Zn1 N1 2.209(3) . ?
Zn1 O1 2.230(2) . ?
S1 C2 1.693(6) . ?
S1 C3 1.702(4) . ?
N1 C3 1.315(5) . ?
N1 C1 1.373(5) . ?
N2 C4 1.304(4) . ?
N2 N3 1.377(4) . ?
N3 C6 1.323(4) . ?
N4 C8 1.496(5) . ?
N4 C7 1.499(4) . ?
N4 C9 1.501(4) . ?
N4 C10 1.507(4) . ?
N5 N6 1.161(6) . ?
N6 N7 1.158(6) . ?
N8 N9 0.899(5) . ?
N9 N10 1.212(6) . ?
O1 C6 1.244(4) . ?
C1 C2 1.341(7) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.462(5) . ?
C4 C5 1.477(6) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.526(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Zn1 N8 115.1(2) . . ?
N5 Zn1 N2 121.42(17) . . ?
N8 Zn1 N2 123.30(18) . . ?
N5 Zn1 N1 102.84(15) . . ?
N8 Zn1 N1 96.46(17) . . ?
N2 Zn1 N1 76.21(13) . . ?
N5 Zn1 O1 96.26(14) . . ?
N8 Zn1 O1 97.18(16) . . ?
N2 Zn1 O1 73.08(10) . . ?
N1 Zn1 O1 149.06(12) . . ?
C2 S1 C3 90.2(2) . . ?
C3 N1 C1 111.2(4) . . ?
C3 N1 Zn1 109.6(3) . . ?
C1 N1 Zn1 138.5(4) . . ?
C4 N2 N3 119.2(3) . . ?
C4 N2 Zn1 120.5(3) . . ?
N3 N2 Zn1 120.2(2) . . ?
C6 N3 N2 108.7(3) . . ?
C8 N4 C7 110.2(3) . . ?
C8 N4 C9 110.0(3) . . ?
C7 N4 C9 112.0(3) . . ?
C8 N4 C10 108.9(3) . . ?
C7 N4 C10 107.2(3) . . ?
C9 N4 C10 108.5(3) . . ?
N6 N5 Zn1 122.5(3) . . ?
N7 N6 N5 178.5(6) . . ?
N9 N8 Zn1 122.7(5) . . ?
N8 N9 N10 169.2(7) . . ?
C6 O1 Zn1 109.3(2) . . ?
C2 C1 N1 114.5(5) . . ?
C2 C1 H1 122.7 . . ?
N1 C1 H1 122.7 . . ?
C1 C2 S1 110.7(4) . . ?
C1 C2 H2 124.6 . . ?
S1 C2 H2 124.6 . . ?
N1 C3 C4 121.7(3) . . ?
N1 C3 S1 113.4(3) . . ?
C4 C3 S1 124.8(3) . . ?
N2 C4 C3 111.8(3) . . ?
N2 C4 C5 125.2(4) . . ?
C3 C4 C5 123.0(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O1 C6 N3 128.5(3) . . ?
O1 C6 C7 116.6(3) . . ?
N3 C6 C7 114.8(3) . . ?
N4 C7 C6 115.2(3) . . ?
N4 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
N4 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
C4 N2 N3 C6 176.6(3) . . . . ?
Zn1 N2 N3 C6 -2.8(4) . . . . ?
Zn1 N8 N9 N10 -97(3) . . . . ?
C3 N1 C1 C2 -0.3(6) . . . . ?
Zn1 N1 C1 C2 168.8(4) . . . . ?
N1 C1 C2 S1 1.0(6) . . . . ?
C3 S1 C2 C1 -1.1(4) . . . . ?
C1 N1 C3 C4 176.8(4) . . . . ?
Zn1 N1 C3 C4 4.4(5) . . . . ?
C1 N1 C3 S1 -0.6(5) . . . . ?
Zn1 N1 C3 S1 -172.91(17) . . . . ?
C2 S1 C3 N1 1.0(3) . . . . ?
C2 S1 C3 C4 -176.3(3) . . . . ?
N3 N2 C4 C3 -178.0(3) . . . . ?
Zn1 N2 C4 C3 1.4(4) . . . . ?
N3 N2 C4 C5 0.7(6) . . . . ?
Zn1 N2 C4 C5 -179.9(3) . . . . ?
N1 C3 C4 N2 -4.1(5) . . . . ?
S1 C3 C4 N2 172.9(3) . . . . ?
N1 C3 C4 C5 177.1(4) . . . . ?
S1 C3 C4 C5 -5.8(5) . . . . ?
Zn1 O1 C6 N3 4.5(5) . . . . ?
Zn1 O1 C6 C7 -179.6(2) . . . . ?
N2 N3 C6 O1 -1.6(5) . . . . ?
N2 N3 C6 C7 -177.5(3) . . . . ?
C8 N4 C7 C6 -52.4(4) . . . . ?
C9 N4 C7 C6 70.4(4) . . . . ?
C10 N4 C7 C6 -170.7(3) . . . . ?
O1 C6 C7 N4 115.2(4) . . . . ?
N3 C6 C7 N4 -68.4(4) . . . . ?

_refine_diff_density_max         0.626
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.061



