# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1425728'
_audit_update_record             
;
2015-11-02 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H13 N5 O2 S2, C4 H8 O'
_chemical_formula_sum            'C25 H21 N5 O3 S2'
_chemical_formula_weight         503.59

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'

_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                   13.7363(14)
_cell_length_b                   7.2021(5)
_cell_length_c                   24.651(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.952(10)
_cell_angle_gamma                90
_cell_volume                     2409.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4252
_cell_measurement_theta_min      3.2040
_cell_measurement_theta_max      21.4690

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60798
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16255
_diffrn_reflns_av_unetI/netI     0.1330
_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.949
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4252
_reflns_number_gt                2095
_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       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  SHELXTL-2014/7
_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)+(0.0095P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4252
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1625
_refine_ls_R_factor_gt           0.0725
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4434(3) 0.8104(6) 0.34833(18) 0.0475(12) Uani 1 1 d . . . . .
C2 C 0.4596(3) 0.9824(5) 0.38268(18) 0.0440(12) Uani 1 1 d . . . . .
C3 C 0.5273(3) 1.1114(5) 0.36922(18) 0.0530(13) Uani 1 1 d . . . . .
H3 H 0.5600 1.0924 0.3394 0.064 Uiso 1 1 calc R U . . .
C4 C 0.5445(3) 1.2680(6) 0.4012(2) 0.0577(14) Uani 1 1 d . . . . .
H4 H 0.5886 1.3579 0.3932 0.069 Uiso 1 1 calc R U . . .
C5 C 0.4956(3) 1.2893(6) 0.44509(19) 0.0574(14) Uani 1 1 d . . . . .
H5 H 0.5065 1.3934 0.4675 0.069 Uiso 1 1 calc R U . . .
C6 C 0.4300(3) 1.1538(6) 0.45553(18) 0.0465(12) Uani 1 1 d . . . . .
C7 C 0.3765(3) 1.1773(6) 0.50391(19) 0.0505(13) Uani 1 1 d . . . . .
C8 C 0.2548(3) 1.0352(6) 0.55309(19) 0.0522(12) Uani 1 1 d . . . . .
C9 C 0.1744(3) 1.0801(6) 0.63243(19) 0.0581(13) Uani 1 1 d . . . . .
C10 C 0.1320(4) 1.1184(7) 0.6783(2) 0.0736(16) Uani 1 1 d . . . . .
H10 H 0.1430 1.2318 0.6962 0.088 Uiso 1 1 calc R U . . .
C11 C 0.0733(4) 0.9865(9) 0.6971(2) 0.0863(18) Uani 1 1 d . . . . .
H11 H 0.0445 1.0106 0.7282 0.104 Uiso 1 1 calc R U . . .
C12 C 0.0566(4) 0.8178(8) 0.6704(2) 0.0907(19) Uani 1 1 d . . . . .
H12 H 0.0168 0.7296 0.6837 0.109 Uiso 1 1 calc R U . . .
C13 C 0.0981(4) 0.7792(7) 0.6244(2) 0.0809(17) Uani 1 1 d . . . . .
H13 H 0.0865 0.6657 0.6065 0.097 Uiso 1 1 calc R U . . .
C14 C 0.1576(4) 0.9121(7) 0.6047(2) 0.0604(14) Uani 1 1 d . . . . .
C15 C 0.3433(3) 0.5319(6) 0.33141(17) 0.0475(12) Uani 1 1 d . . . . .
C16 C 0.3307(3) 0.2594(5) 0.27350(17) 0.0419(11) Uani 1 1 d . . . . .
C17 C 0.3317(3) 0.1081(5) 0.23924(18) 0.0526(13) Uani 1 1 d . . . . .
H17 H 0.3749 0.1036 0.2137 0.063 Uiso 1 1 calc R U . . .
C18 C 0.2673(4) -0.0362(6) 0.2436(2) 0.0617(14) Uani 1 1 d . . . . .
H18 H 0.2670 -0.1399 0.2211 0.074 Uiso 1 1 calc R U . . .
C19 C 0.2026(4) -0.0261(6) 0.2817(2) 0.0660(15) Uani 1 1 d . . . . .
H19 H 0.1589 -0.1234 0.2840 0.079 Uiso 1 1 calc R U . . .
C20 C 0.2017(3) 0.1234(6) 0.31597(19) 0.0594(14) Uani 1 1 d . . . . .
H20 H 0.1582 0.1278 0.3413 0.071 Uiso 1 1 calc R U . . .
C21 C 0.2673(3) 0.2688(6) 0.31205(18) 0.0474(12) Uani 1 1 d . . . . .
C22 C 0.2299(4) 0.5704(6) 0.4667(2) 0.0752(16) Uani 1 1 d . . . . .
H22A H 0.2545 0.5891 0.5054 0.090 Uiso 1 1 calc R U . . .
H22B H 0.2726 0.4827 0.4520 0.090 Uiso 1 1 calc R U . . .
C23 C 0.1275(5) 0.4995(8) 0.4593(3) 0.126(3) Uani 1 1 d . . . . .
H23A H 0.1202 0.3948 0.4343 0.152 Uiso 1 1 calc R U . . .
H23B H 0.1104 0.4597 0.4942 0.152 Uiso 1 1 calc R U . . .
C24 C 0.0656(5) 0.6487(9) 0.4373(3) 0.166(4) Uani 1 1 d . . . . .
H24A H 0.0321 0.7020 0.4655 0.199 Uiso 1 1 calc R U . . .
H24B H 0.0163 0.6048 0.4075 0.199 Uiso 1 1 calc R U . . .
C25 C 0.1279(4) 0.7849(7) 0.4174(2) 0.0902(19) Uani 1 1 d . . . . .
H25A H 0.1175 0.7842 0.3776 0.108 Uiso 1 1 calc R U . . .
H25B H 0.1118 0.9076 0.4296 0.108 Uiso 1 1 calc R U . . .
N1 N 0.3694(3) 0.6954(5) 0.35918(15) 0.0498(11) Uani 1 1 d . . . . .
N2 N 0.4103(2) 1.0026(4) 0.42502(14) 0.0424(9) Uani 1 1 d . . . . .
N3 N 0.3081(3) 1.0457(5) 0.50949(16) 0.0532(11) Uani 1 1 d . . . . .
N4 N 0.2040(3) 0.8884(5) 0.55899(16) 0.0652(12) Uani 1 1 d . . . . .
N5 N 0.2752(3) 0.4264(5) 0.34485(14) 0.0541(11) Uani 1 1 d . . . . .
O1 O 0.4911(2) 0.7769(3) 0.31219(12) 0.0608(9) Uani 1 1 d . . . . .
O2 O 0.3953(2) 1.3051(4) 0.53656(13) 0.0614(9) Uani 1 1 d . . . . .
O3 O 0.2274(3) 0.7429(4) 0.43772(13) 0.0616(9) Uani 1 1 d . . . . .
S1 S 0.40390(9) 0.45765(14) 0.27763(5) 0.0499(3) Uani 1 1 d . . . . .
S2 S 0.25442(10) 1.21422(16) 0.60025(5) 0.0645(4) Uani 1 1 d . . . . .
H1 H 0.335(2) 0.732(4) 0.3823(13) 0.016(10) Uiso 1 1 d . . . . .
H3A H 0.294(3) 0.955(5) 0.4834(17) 0.077(16) Uiso 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
C1 O1 1.210(4) . ?
C1 N1 1.369(5) . ?
C1 C2 1.497(5) . ?
C2 N2 1.338(5) . ?
C2 C3 1.390(5) . ?
C3 C4 1.376(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(5) . ?
C5 H5 0.9300 . ?
C6 N2 1.327(4) . ?
C6 C7 1.505(5) . ?
C7 O2 1.223(4) . ?
C7 N3 1.356(5) . ?
C8 N4 1.287(5) . ?
C8 N3 1.394(5) . ?
C8 S2 1.737(4) . ?
C9 C10 1.378(6) . ?
C9 C14 1.391(5) . ?
C9 S2 1.744(4) . ?
C10 C11 1.373(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(6) . ?
C13 H13 0.9300 . ?
C14 N4 1.389(5) . ?
C15 N5 1.288(5) . ?
C15 N1 1.381(5) . ?
C15 S1 1.755(4) . ?
C16 C17 1.379(5) . ?
C16 C21 1.388(5) . ?
C16 S1 1.740(4) . ?
C17 C18 1.380(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.392(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.394(5) . ?
C20 H20 0.9300 . ?
C21 N5 1.388(5) . ?
C22 O3 1.431(5) . ?
C22 C23 1.481(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.424(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.437(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O3 1.413(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
N1 H1 0.84(3) . ?
N3 H3A 0.91(4) . ?

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
O1 C1 N1 121.8(4) . . ?
O1 C1 C2 122.1(4) . . ?
N1 C1 C2 116.1(4) . . ?
N2 C2 C3 123.5(4) . . ?
N2 C2 C1 118.8(4) . . ?
C3 C2 C1 117.6(4) . . ?
C4 C3 C2 118.2(4) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C5 C4 C3 119.0(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 118.9(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
N2 C6 C5 123.8(4) . . ?
N2 C6 C7 117.4(4) . . ?
C5 C6 C7 118.8(4) . . ?
O2 C7 N3 122.5(4) . . ?
O2 C7 C6 121.8(4) . . ?
N3 C7 C6 115.6(4) . . ?
N4 C8 N3 119.4(4) . . ?
N4 C8 S2 118.4(4) . . ?
N3 C8 S2 122.2(4) . . ?
C10 C9 C14 121.2(5) . . ?
C10 C9 S2 129.7(4) . . ?
C14 C9 S2 109.0(4) . . ?
C11 C10 C9 119.0(5) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 120.5(5) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.3(5) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
N4 C14 C9 116.3(4) . . ?
N4 C14 C13 124.5(5) . . ?
C9 C14 C13 119.2(5) . . ?
N5 C15 N1 121.2(4) . . ?
N5 C15 S1 117.6(3) . . ?
N1 C15 S1 121.1(3) . . ?
C17 C16 C21 121.7(4) . . ?
C17 C16 S1 128.6(3) . . ?
C21 C16 S1 109.8(3) . . ?
C16 C17 C18 118.7(4) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C17 C18 C19 119.8(4) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 121.7(4) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C21 118.7(4) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C16 C21 N5 116.0(4) . . ?
C16 C21 C20 119.5(4) . . ?
N5 C21 C20 124.5(4) . . ?
O3 C22 C23 106.8(4) . . ?
O3 C22 H22A 110.4 . . ?
C23 C22 H22A 110.4 . . ?
O3 C22 H22B 110.4 . . ?
C23 C22 H22B 110.4 . . ?
H22A C22 H22B 108.6 . . ?
C24 C23 C22 106.7(5) . . ?
C24 C23 H23A 110.4 . . ?
C22 C23 H23A 110.4 . . ?
C24 C23 H23B 110.4 . . ?
C22 C23 H23B 110.4 . . ?
H23A C23 H23B 108.6 . . ?
C23 C24 C25 107.0(6) . . ?
C23 C24 H24A 110.3 . . ?
C25 C24 H24A 110.3 . . ?
C23 C24 H24B 110.3 . . ?
C25 C24 H24B 110.3 . . ?
H24A C24 H24B 108.6 . . ?
O3 C25 C24 109.1(5) . . ?
O3 C25 H25A 109.9 . . ?
C24 C25 H25A 109.9 . . ?
O3 C25 H25B 109.9 . . ?
C24 C25 H25B 109.9 . . ?
H25A C25 H25B 108.3 . . ?
C1 N1 C15 124.2(4) . . ?
C1 N1 H1 118(2) . . ?
C15 N1 H1 118(2) . . ?
C6 N2 C2 116.6(4) . . ?
C7 N3 C8 124.8(4) . . ?
C7 N3 H3A 120(3) . . ?
C8 N3 H3A 115(3) . . ?
C8 N4 C14 108.4(4) . . ?
C15 N5 C21 109.1(4) . . ?
C25 O3 C22 108.0(4) . . ?
C16 S1 C15 87.5(2) . . ?
C8 S2 C9 87.8(2) . . ?

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.203
_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_CuL1
_database_code_depnum_ccdc_archive 'CCDC 1425729'
_audit_update_record             
;
2015-11-02 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H13 Cu N5 O3 S2 '
_chemical_formula_sum            'C21 H13 Cl0 Cu N5 O3 S2'
_chemical_formula_weight         511.02

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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.075(5)
_cell_length_b                   12.054(5)
_cell_length_c                   26.823(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1964.2(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3445
_cell_measurement_theta_min      2.836
_cell_measurement_theta_max      25.0

_exptl_crystal_description       cube
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_F_000             1036
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    1.362
_shelx_estimated_absorpt_T_min   0.772
_shelx_estimated_absorpt_T_max   0.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23961
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.836
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3445
_reflns_number_gt                3305
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  SHELXTL-2014/7
_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)+(0.0382P)²+0.5745P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1307 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3445
_refine_ls_number_parameters     297
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0730
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu01 Cu 0.53348(8) 0.03433(4) 0.55539(2) 0.02818(15) Uani 1 1 d D . . . .
S1 S 1.00859(17) 0.08901(9) 0.41973(4) 0.0300(2) Uani 1 1 d . . . . .
S2 S 0.03625(19) -0.06778(9) 0.68081(4) 0.0351(3) Uani 1 1 d . . . . .
N5 N 0.6213(5) 0.0040(3) 0.43634(12) 0.0273(8) Uani 1 1 d . . . . .
O1W O 0.3747(5) -0.0639(3) 0.51297(12) 0.0402(8) Uani 1 1 d D . . . .
O1 O 1.1113(5) 0.1694(3) 0.50988(12) 0.0452(9) Uani 1 1 d . . . . .
O2 O 0.3460(5) 0.0808(3) 0.69969(11) 0.0421(8) Uani 1 1 d . . . . .
C20 C 0.5138(7) -0.0541(3) 0.35114(14) 0.0308(9) Uani 1 1 d . . . . .
H20 H 0.3801 -0.0835 0.3616 0.037 Uiso 1 1 calc R U . . .
N1 N 0.7764(5) 0.0782(3) 0.50833(12) 0.0274(8) Uani 1 1 d . . . . .
C21 C 0.6599(7) -0.0072(3) 0.38567(15) 0.0275(10) Uani 1 1 d . . . . .
N4 N 0.0707(6) -0.0925(3) 0.58438(13) 0.0290(8) Uani 1 1 d . . . . .
N2 N 0.7031(6) 0.1253(3) 0.59950(13) 0.0262(8) Uani 1 1 d . . . . .
C17 C 0.9218(7) 0.0303(4) 0.31924(15) 0.0336(10) Uani 1 1 d . . . . .
H17 H 1.0574 0.0570 0.3085 0.040 Uiso 1 1 calc R U . . .
C4 C 0.9427(8) 0.2548(4) 0.66154(17) 0.0365(11) Uani 1 1 d . . . . .
H4 H 1.0252 0.2993 0.6828 0.044 Uiso 1 1 calc R U . . .
C6 C 0.6319(7) 0.1412(4) 0.64582(15) 0.0271(9) Uani 1 1 d . . . . .
C9 C -0.1589(7) -0.1488(4) 0.65042(17) 0.0329(10) Uani 1 1 d . . . . .
N3 N 0.3488(5) 0.0196(3) 0.61758(12) 0.0273(8) Uani 1 1 d . . . . .
C19 C 0.5710(8) -0.0559(4) 0.30163(16) 0.0350(11) Uani 1 1 d . . . . .
H19 H 0.4731 -0.0845 0.2783 0.042 Uiso 1 1 calc R U . . .
C1 C 0.9400(7) 0.1405(4) 0.52953(16) 0.0302(10) Uani 1 1 d . . . . .
C14 C -0.1133(7) -0.1518(4) 0.59925(17) 0.0300(10) Uani 1 1 d . . . . .
C18 C 0.7740(8) -0.0153(4) 0.28601(16) 0.0352(11) Uani 1 1 d . . . . .
H18 H 0.8109 -0.0191 0.2524 0.042 Uiso 1 1 calc R U . . .
C8 C 0.1634(6) -0.0442(4) 0.62278(15) 0.0292(10) Uani 1 1 d . . . . .
C16 C 0.8619(6) 0.0352(4) 0.36931(15) 0.0267(9) Uani 1 1 d . . . . .
C11 C -0.4815(8) -0.2574(4) 0.63806(19) 0.0441(12) Uani 1 1 d . . . . .
H11 H -0.6061 -0.2924 0.6507 0.053 Uiso 1 1 calc R U . . .
C22 C 0.7835(6) 0.0534(3) 0.45874(15) 0.0252(9) Uani 1 1 d . . . . .
C2 C 0.8889(7) 0.1694(4) 0.58245(16) 0.0280(10) Uani 1 1 d . . . . .
C10 C -0.3428(8) -0.2011(4) 0.66988(19) 0.0403(12) Uani 1 1 d . . . . .
H10 H -0.3722 -0.1983 0.7039 0.048 Uiso 1 1 calc R U . . .
C7 C 0.4245(7) 0.0778(4) 0.65761(15) 0.0291(10) Uani 1 1 d . . . . .
C12 C -0.4369(8) -0.2623(4) 0.5874(2) 0.0441(12) Uani 1 1 d . . . . .
H12 H -0.5317 -0.3013 0.5665 0.053 Uiso 1 1 calc R U . . .
C13 C -0.2540(8) -0.2105(4) 0.56723(19) 0.0398(12) Uani 1 1 d . . . . .
H13 H -0.2250 -0.2145 0.5332 0.048 Uiso 1 1 calc R U . . .
C3 C 1.0158(8) 0.2357(3) 0.61329(16) 0.0332(10) Uani 1 1 d . . . . .
H3 H 1.1467 0.2667 0.6019 0.040 Uiso 1 1 calc R U . . .
C5 C 0.7467(7) 0.2079(4) 0.67831(17) 0.0331(10) Uani 1 1 d . . . . .
H5 H 0.6952 0.2212 0.7104 0.040 Uiso 1 1 calc R U . . .
H1A H 0.245(6) -0.072(6) 0.527(2) 0.09(2) Uiso 1 1 d D . . . .
H1B H 0.384(10) -0.045(5) 0.4826(10) 0.09(2) Uiso 1 1 d 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
Cu01 O1W 1.904(3) . ?
Cu01 N2 1.914(3) . ?
Cu01 N1 2.013(4) . ?
Cu01 N3 2.018(3) . ?
Cu01 H1B 2.36(4) . ?
S1 C16 1.745(4) . ?
S1 C22 1.775(4) . ?
S2 C9 1.739(5) . ?
S2 C8 1.761(4) . ?
N5 C22 1.298(5) . ?
N5 C21 1.386(5) . ?
O1W H1A 0.88(3) . ?
O1W H1B 0.85(3) . ?
O1 C1 1.218(5) . ?
O2 C7 1.226(5) . ?
C20 C19 1.373(6) . ?
C20 C21 1.402(6) . ?
C20 H20 0.9300 . ?
N1 C22 1.364(5) . ?
N1 C1 1.369(5) . ?
C21 C16 1.400(6) . ?
N4 C8 1.310(6) . ?
N4 C14 1.386(6) . ?
N2 C6 1.329(5) . ?
N2 C2 1.329(6) . ?
C17 C18 1.380(6) . ?
C17 C16 1.393(6) . ?
C17 H17 0.9300 . ?
C4 C5 1.392(6) . ?
C4 C3 1.387(6) . ?
C4 H4 0.9300 . ?
C6 C5 1.376(6) . ?
C6 C7 1.507(6) . ?
C9 C10 1.385(6) . ?
C9 C14 1.400(6) . ?
N3 C7 1.362(5) . ?
N3 C8 1.371(5) . ?
C19 C18 1.391(7) . ?
C19 H19 0.9300 . ?
C1 C2 1.494(6) . ?
C14 C13 1.403(7) . ?
C18 H18 0.9300 . ?
C11 C10 1.378(7) . ?
C11 C12 1.387(7) . ?
C11 H11 0.9300 . ?
C2 C3 1.385(6) . ?
C10 H10 0.9300 . ?
C12 C13 1.385(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?

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
O1W Cu01 N2 176.46(16) . . ?
O1W Cu01 N1 99.20(14) . . ?
N2 Cu01 N1 80.95(14) . . ?
O1W Cu01 N3 99.08(15) . . ?
N2 Cu01 N3 80.70(15) . . ?
N1 Cu01 N3 161.64(14) . . ?
O1W Cu01 H1B 19.5(10) . . ?
N2 Cu01 H1B 162.2(11) . . ?
N1 Cu01 H1B 82.5(12) . . ?
N3 Cu01 H1B 115.8(12) . . ?
C16 S1 C22 88.48(19) . . ?
C9 S2 C8 88.6(2) . . ?
C22 N5 C21 111.8(3) . . ?
Cu01 O1W H1A 106(5) . . ?
Cu01 O1W H1B 112(4) . . ?
H1A O1W H1B 120(6) . . ?
C19 C20 C21 119.0(4) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C22 N1 C1 120.2(4) . . ?
C22 N1 Cu01 125.3(3) . . ?
C1 N1 Cu01 114.6(3) . . ?
N5 C21 C16 114.8(4) . . ?
N5 C21 C20 125.5(4) . . ?
C16 C21 C20 119.7(4) . . ?
C8 N4 C14 110.5(4) . . ?
C6 N2 C2 122.7(4) . . ?
C6 N2 Cu01 119.0(3) . . ?
C2 N2 Cu01 118.3(3) . . ?
C18 C17 C16 118.0(4) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C5 C4 C3 120.5(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
N2 C6 C5 120.8(4) . . ?
N2 C6 C7 113.3(4) . . ?
C5 C6 C7 126.0(4) . . ?
C10 C9 C14 121.1(4) . . ?
C10 C9 S2 129.0(4) . . ?
C14 C9 S2 109.8(3) . . ?
C7 N3 C8 119.1(3) . . ?
C7 N3 Cu01 114.8(3) . . ?
C8 N3 Cu01 126.1(3) . . ?
C20 C19 C18 120.7(4) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
O1 C1 N1 126.7(4) . . ?
O1 C1 C2 121.5(4) . . ?
N1 C1 C2 111.8(4) . . ?
N4 C14 C13 125.1(4) . . ?
N4 C14 C9 115.4(4) . . ?
C13 C14 C9 119.5(4) . . ?
C17 C18 C19 121.5(4) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
N4 C8 N3 121.5(4) . . ?
N4 C8 S2 115.8(3) . . ?
N3 C8 S2 122.7(3) . . ?
C17 C16 C21 121.1(4) . . ?
C17 C16 S1 129.0(3) . . ?
C21 C16 S1 109.9(3) . . ?
C10 C11 C12 120.6(5) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
N5 C22 N1 121.9(4) . . ?
N5 C22 S1 115.0(3) . . ?
N1 C22 S1 123.1(3) . . ?
N2 C2 C3 119.9(4) . . ?
N2 C2 C1 114.2(4) . . ?
C3 C2 C1 125.9(4) . . ?
C11 C10 C9 118.9(5) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
O2 C7 N3 127.6(4) . . ?
O2 C7 C6 120.2(4) . . ?
N3 C7 C6 112.2(4) . . ?
C13 C12 C11 121.3(5) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 118.5(5) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C2 C3 C4 118.3(4) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C6 C5 C4 117.8(4) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_znl-4
_database_code_depnum_ccdc_archive 'CCDC 1425730'
_audit_update_record             
;
2015-11-21 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;
_audit_creation_date             2015-11-19
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r3563)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 Cl N6 O7 S2 Zn, Cl O4, H2 O'
_chemical_formula_sum            'C26 H22 Cl2 N6 O12 S2 Zn'
_chemical_formula_weight         810.88
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.145(5)
_cell_length_b                   7.935(5)
_cell_length_c                   19.780(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.505(16)
_cell_angle_gamma                90
_cell_volume                     1748.0(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.868
_shelx_estimated_absorpt_T_min   0.803
_exptl_absorpt_coefficient_mu    1.041
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_av_unetI/netI     0.0853
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16089
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.092
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2089
_reflns_number_total             3081
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3081
_refine_ls_number_restraints     202
_refine_ls_R_factor_all          0.1610
_refine_ls_R_factor_gt           0.1232
_refine_ls_restrained_S_all      1.166
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1249P)²+15.6474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3315
_refine_ls_wR_factor_ref         0.3509
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1_3-O1_3
 O1_4-O1_4
 0.84 with sigma of 0.01
 O1_3-O1_3
 O1_4-O1_4
 0.84 with sigma of 0.01
 Cl1_1-O1_1 \\sim Cl1_1-O2_1 \\sim Cl1_1-O3_1 \\sim Cl1_1-O4_1
 Cl1_2-O1_2 \\sim Cl1_2-O2_2 \\sim Cl1_2-O3_2 \\sim Cl1_2-O4_2
 with sigma of 0.02
 O1_1-O3_1 \\sim O2_1-O4_1 \\sim O1_1-O4_1 \\sim O2_1-O3_1 \\sim O1_1-O2_1
\\sim O3_1-O4_1
 O1_2-O3_2 \\sim O2_2-O4_2 \\sim O1_2-O4_2 \\sim O2_2-O3_2 \\sim O1_2-O2_2
\\sim O3_2-O4_2
 with sigma of 0.04
 Cl1_1-O1_1 \\sim Cl1_1-O2_1 \\sim Cl1_1-O3_1 \\sim Cl1_1-O4_1
 Cl1_2-O1_2 \\sim Cl1_2-O2_2 \\sim Cl1_2-O3_2 \\sim Cl1_2-O4_2
 with sigma of 0.02
 O1_1-O3_1 \\sim O2_1-O4_1 \\sim O1_1-O4_1 \\sim O2_1-O3_1 \\sim O1_1-O2_1
\\sim O3_1-O4_1
 O1_2-O3_2 \\sim O2_2-O4_2 \\sim O1_2-O4_2 \\sim O2_2-O3_2 \\sim O1_2-O2_2
\\sim O3_2-O4_2
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Cl1_1 \\sim O1_1 \\sim O2_1 \\sim O3_1 \\sim O4_1 \\sim Cl1_2 \\sim O1_2 \\sim
O2_2 \\sim O3_2 \\sim O4_2: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Cl1_1 \\sim O1_1 \\sim O2_1 \\sim O3_1 \\sim O4_1 \\sim Cl1_2 \\sim O1_2 \\sim
O2_2 \\sim O3_2 \\sim O4_2: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Uanis(O4_2) = Uanis(O1_3)
Uanis(O1_1) = Uanis(O1_4)
4. Rigid body (RIGU) restrains
 Cl1_1, O1_1, O2_1, O3_1, O4_1
 Cl1_2, O1_2, O2_2, O3_2, O4_2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl1_1, O1_1, O2_1, O3_1, O4_1
 Cl1_2, O1_2, O2_2, O3_2, O4_2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: Cl1(0.5) O1(0.5) O2(0.5) O3(0.5) O4(0.5) Cl1(0.5) O1(0.5) O2(0.5)
 O3(0.5) O4(0.5) O1(0.5) H1A(0.5) H1B(0.5) O1(0.5) H1A(0.5) H1B(0.5)
6.a Riding coordinates:
 O1(H1A,H1B), O1(H1A,H1B)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), N3(H3A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1372(11) -0.1522(16) 0.3473(8) 0.066(3) Uani 1 1 d . . . . .
H1 H -0.2013 -0.1644 0.3613 0.079 Uiso 1 1 calc R . . . .
C2 C -0.1508(13) -0.2110(19) 0.2785(8) 0.076(4) Uani 1 1 d . . . . .
H2 H -0.2209 -0.2645 0.2475 0.092 Uiso 1 1 calc R . . . .
C3 C -0.0544(13) -0.1865(17) 0.2576(7) 0.067(3) Uani 1 1 d . . . . .
H3 H -0.0607 -0.2203 0.2112 0.080 Uiso 1 1 calc R . . . .
C4 C 0.0517(11) -0.1108(15) 0.3069(6) 0.055(3) Uani 1 1 d . . . . .
H4 H 0.1175 -0.0963 0.2946 0.066 Uiso 1 1 calc R . . . .
C5 C 0.0548(9) -0.0584(13) 0.3746(6) 0.047(3) Uani 1 1 d . . . . .
C6 C 0.1615(10) 0.0276(12) 0.4311(6) 0.044(2) Uani 1 1 d . . . . .
C7 C 0.3463(9) 0.1377(13) 0.4574(6) 0.046(3) Uani 1 1 d . . . . .
C8 C 0.5188(10) 0.2798(15) 0.5540(7) 0.055(3) Uani 1 1 d . . . . .
C9 C 0.6047(12) 0.3659(19) 0.6133(8) 0.076(4) Uani 1 1 d . . . . .
H9 H 0.5915 0.3908 0.6554 0.091 Uiso 1 1 calc R . . . .
C10 C 0.7085(12) 0.4120(19) 0.6072(9) 0.076(4) Uani 1 1 d . . . . .
H10 H 0.7706 0.4605 0.6471 0.091 Uiso 1 1 calc R . . . .
C11 C 0.7211(11) 0.3862(15) 0.5414(9) 0.069(4) Uani 1 1 d . . . . .
H11 H 0.7918 0.4224 0.5383 0.083 Uiso 1 1 calc R . . . .
C12 C 0.6382(11) 0.3125(15) 0.4819(8) 0.064(3) Uani 1 1 d . . . . .
H12 H 0.6490 0.2991 0.4383 0.076 Uiso 1 1 calc R . . . .
C13 C 0.5340(10) 0.2569(15) 0.4895(7) 0.056(3) Uani 1 1 d . . . . .
N1 N -0.0376(8) -0.0792(11) 0.3945(5) 0.050(2) Uani 1 1 d . . . . .
N2 N 0.2478(8) 0.0661(12) 0.4078(5) 0.048(2) Uani 1 1 d . . . . .
N3 N 0.4363(8) 0.1751(12) 0.4365(5) 0.053(2) Uani 1 1 d . . . . .
H3A H 0.4336 0.1501 0.3935 0.064 Uiso 1 1 calc R . . . .
O1 O 0.1623(7) 0.0541(10) 0.4937(4) 0.057(2) Uani 1 1 d . . . . .
S1 S 0.3788(3) 0.2009(4) 0.54701(17) 0.0533(8) Uani 1 1 d . . . . .
Zn1 Zn 0.0000 0.0000 0.5000 0.0547(7) Uani 1 2 d S T P . .
Cl1_1 Cl 0.4406(7) 0.4841(10) 0.7525(4) 0.0790(19) Uani 0.5 1 d D U . A 1
O1_1 O 0.460(3) 0.352(3) 0.7977(16) 0.110(6) Uani 0.5 1 d D U . A 1
O2_1 O 0.5427(17) 0.557(3) 0.7642(14) 0.130(7) Uani 0.5 1 d D U . A 1
O3_1 O 0.3930(19) 0.430(3) 0.6840(9) 0.105(6) Uani 0.5 1 d D U . A 1
O4_1 O 0.3655(19) 0.576(3) 0.7673(14) 0.134(7) Uani 0.5 1 d D U . A 1
Cl1_2 Cl -0.0839(7) 0.3702(8) 0.4107(5) 0.079(2) Uani 0.5 1 d D U . B 1
O1_2 O -0.130(2) 0.513(2) 0.4185(14) 0.116(6) Uani 0.5 1 d D U . B 1
O2_2 O 0.0072(19) 0.393(3) 0.3924(15) 0.137(7) Uani 0.5 1 d D U . B 1
O3_2 O -0.168(2) 0.293(3) 0.3561(12) 0.141(7) Uani 0.5 1 d D U . B 1
O4_2 O -0.049(3) 0.278(3) 0.4703(12) 0.093(6) Uani 0.5 1 d D U . B 1
O1_3 O -0.083(3) 0.236(3) 0.4542(15) 0.093(6) Uani 0.5 1 d D . . B 2
H1A_3 H -0.0898 0.2611 0.4109 0.140 Uiso 0.5 1 d R . . B 2
H1B_3 H -0.1230 0.3054 0.4680 0.140 Uiso 0.5 1 d R . . B 2
O1_4 O 0.423(3) 0.383(4) 0.8023(18) 0.110(6) Uani 0.5 1 d D . . C 2
H1A_4 H 0.4043 0.2931 0.7769 0.165 Uiso 0.5 1 d R . . C 2
H1B_4 H 0.4904 0.4183 0.8051 0.165 Uiso 0.5 1 d R . . C 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
O1_4 H1B_4 0.8500 . ?
Cl1_2 O4_2 1.308(16) . ?
Cl1_2 O3_2 1.304(15) . ?
Cl1_1 O4_1 1.290(15) . ?
O1_3 H1B_3 0.8499 . ?
O1_4 H1A_4 0.8501 . ?
Cl1_2 O2_2 1.306(15) . ?
Cl1_1 O3_1 1.314(14) . ?
O1_3 H1A_3 0.8500 . ?
Cl1_1 O1_1 1.335(16) . ?
Cl1_2 O1_2 1.301(14) . ?
Cl1_1 O2_1 1.303(15) . ?
C1 H1 0.9300 . ?
C1 C2 1.384(19) . ?
C1 N1 1.330(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.402(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.403(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(16) . ?
C5 C6 1.495(15) . ?
C5 N1 1.339(14) . ?
C6 N2 1.338(13) . ?
C6 O1 1.253(12) . ?
C7 N2 1.334(14) . ?
C7 N3 1.348(13) . ?
C7 S1 1.729(12) . ?
C8 C9 1.398(17) . ?
C8 C13 1.372(17) . ?
C8 S1 1.765(11) . ?
C9 H9 0.9300 . ?
C9 C10 1.362(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.39(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.339(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.404(16) . ?
C13 N3 1.391(15) . ?
N1 Zn1 2.049(9) . ?
N3 H3A 0.8600 . ?
O1 Zn1 2.069(7) . ?
Zn1 O1_3 2.15(3) 3_556 ?
Zn1 O1_3 2.15(3) . ?
Zn1 O4_2 2.30(2) 3_556 ?
Zn1 O4_2 2.30(2) . ?
Zn1 N1 2.049(9) 3_556 ?
Zn1 O1 2.069(7) 3_556 ?

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
O1_2 Cl1_2 O2_2 111.6(14) . . ?
C2 C1 H1 118.1 . . ?
N1 C1 H1 118.1 . . ?
N1 C1 C2 123.7(12) . . ?
O2_2 Cl1_2 O4_2 108.6(16) . . ?
O4_1 Cl1_1 O2_1 114.6(16) . . ?
O2_1 Cl1_1 O3_1 109.0(14) . . ?
O3_1 Cl1_1 O1_1 108.9(16) . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.1(12) . . ?
O1_2 Cl1_2 O4_2 112.6(16) . . ?
C3 C2 H2 121.4 . . ?
H1A_3 O1_3 H1B_3 109.5 . . ?
H1A_4 O1_4 H1B_4 109.5 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.9(12) . . ?
O4_1 Cl1_1 O3_1 110.9(14) . . ?
C4 C3 H3 120.1 . . ?
O4_1 Cl1_1 O1_1 104.2(15) . . ?
O2_1 Cl1_1 O1_1 109.0(16) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.5(11) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 122.6(10) . . ?
O1_2 Cl1_2 O3_2 106.0(15) . . ?
N1 C5 C4 122.9(10) . . ?
O3_2 Cl1_2 O2_2 107.6(15) . . ?
N1 C5 C6 114.5(10) . . ?
O3_2 Cl1_2 O4_2 110.4(15) . . ?
Cl1_2 O4_2 Zn1 136.7(19) . . ?
O1_3 Zn1 O1_3 180.0 . 3_556 ?
O4_2 Zn1 O4_2 180.0(11) 3_556 . ?
N2 C6 C5 114.3(9) . . ?
O1 C6 C5 118.6(9) . . ?
O1 C6 N2 127.1(10) . . ?
N2 C7 N3 117.8(10) . . ?
N2 C7 S1 130.4(8) . . ?
N3 C7 S1 111.7(8) . . ?
C9 C8 S1 127.8(10) . . ?
C13 C8 C9 120.8(12) . . ?
C13 C8 S1 111.2(9) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 C8 117.7(14) . . ?
C10 C9 H9 121.2 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(13) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 117.9 . . ?
C12 C11 C10 124.3(13) . . ?
C12 C11 H11 117.9 . . ?
C11 C12 H12 122.0 . . ?
C11 C12 C13 116.0(13) . . ?
C13 C12 H12 122.0 . . ?
C8 C13 C12 121.2(12) . . ?
C8 C13 N3 111.9(10) . . ?
N3 C13 C12 126.9(12) . . ?
C1 N1 C5 118.8(11) . . ?
C1 N1 Zn1 128.2(9) . . ?
C5 N1 Zn1 112.9(7) . . ?
C7 N2 C6 116.1(9) . . ?
C7 N3 C13 115.0(10) . . ?
C7 N3 H3A 122.5 . . ?
C13 N3 H3A 122.5 . . ?
C6 O1 Zn1 113.1(7) . . ?
C7 S1 C8 90.1(5) . . ?
N1 Zn1 O4_2 84.0(7) 3_556 . ?
N1 Zn1 O1_3 92.2(9) . 3_556 ?
N1 Zn1 O1_3 87.8(9) . . ?
N1 Zn1 O4_2 96.0(7) . . ?
N1 Zn1 O1_3 92.2(9) 3_556 . ?
N1 Zn1 O1_3 87.8(9) 3_556 3_556 ?
N1 Zn1 O4_2 84.0(7) . 3_556 ?
N1 Zn1 O4_2 96.0(7) 3_556 3_556 ?
N1 Zn1 N1 180.0(5) 3_556 . ?
N1 Zn1 O1 80.4(3) 3_556 3_556 ?
N1 Zn1 O1 99.6(3) 3_556 . ?
N1 Zn1 O1 99.6(3) . 3_556 ?
N1 Zn1 O1 80.4(3) . . ?
O1 Zn1 O1 180.0 . 3_556 ?
O1 Zn1 O1_3 84.8(9) 3_556 . ?
O1 Zn1 O4_2 93.4(8) . 3_556 ?
O1 Zn1 O4_2 86.6(9) . . ?
O1 Zn1 O4_2 86.6(9) 3_556 3_556 ?
O1 Zn1 O4_2 93.4(8) 3_556 . ?
O1 Zn1 O1_3 84.8(9) . 3_556 ?
O1 Zn1 O1_3 95.2(9) . . ?
O1 Zn1 O1_3 95.2(9) 3_556 3_556 ?
Zn1 O1_3 H1A_3 118.1 . . ?
Zn1 O1_3 H1B_3 131.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2_2 Cl1_2 O4_2 Zn1 -73(3) . . . . ?
O3_2 Cl1_2 O4_2 Zn1 45(3) . . . . ?
O1_2 Cl1_2 O4_2 Zn1 163(2) . . . . ?
C1 C2 C3 C4 2(2) . . . . ?
C2 C1 N1 C5 1.1(19) . . . . ?
C2 C1 N1 Zn1 -175.7(10) . . . . ?
C2 C3 C4 C5 -1.8(19) . . . . ?
C3 C4 C5 C6 -178.5(10) . . . . ?
C3 C4 C5 N1 0.9(17) . . . . ?
C4 C5 C6 N2 7.0(15) . . . . ?
C4 C5 C6 O1 -172.2(10) . . . . ?
C4 C5 N1 C1 -0.5(17) . . . . ?
C4 C5 N1 Zn1 176.7(8) . . . . ?
C5 C6 N2 C7 -177.8(9) . . . . ?
C5 C6 O1 Zn1 -8.2(12) . . . . ?
C6 C5 N1 C1 179.0(10) . . . . ?
C6 C5 N1 Zn1 -3.8(11) . . . . ?
C8 C9 C10 C11 6(2) . . . . ?
C8 C13 N3 C7 1.3(14) . . . . ?
C9 C8 C13 C12 2.8(19) . . . . ?
C9 C8 C13 N3 -177.4(12) . . . . ?
C9 C8 S1 C7 176.5(13) . . . . ?
C9 C10 C11 C12 -2(2) . . . . ?
C10 C11 C12 C13 -1.2(19) . . . . ?
C11 C12 C13 C8 0.8(17) . . . . ?
C11 C12 C13 N3 -179.0(11) . . . . ?
C12 C13 N3 C7 -178.8(11) . . . . ?
C13 C8 C9 C10 -6(2) . . . . ?
C13 C8 S1 C7 0.6(9) . . . . ?
N1 C1 C2 C3 -2(2) . . . . ?
N1 C5 C6 N2 -172.5(9) . . . . ?
N1 C5 C6 O1 8.3(14) . . . . ?
N2 C6 O1 Zn1 172.7(9) . . . . ?
N2 C7 N3 C13 177.0(10) . . . . ?
N2 C7 S1 C8 -177.3(11) . . . . ?
N3 C7 N2 C6 178.6(9) . . . . ?
N3 C7 S1 C8 0.1(9) . . . . ?
O1 C6 N2 C7 1.4(16) . . . . ?
S1 C7 N2 C6 -4.1(15) . . . . ?
S1 C7 N3 C13 -0.8(12) . . . . ?
S1 C8 C9 C10 178.5(11) . . . . ?
S1 C8 C13 C12 179.0(9) . . . . ?
S1 C8 C13 N3 -1.2(13) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
