# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_rcrtnz68
_database_code_depnum_ccdc_archive 'CCDC 1820833'
_audit_update_record             
;
2018-01-31 deposited with the CCDC.
2018-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        compound_7
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H52 Cl4 Cu2 N12 O16 S4'
_chemical_formula_sum            'C32 H52 Cl4 Cu2 N12 O16 S4'
_chemical_formula_weight         1257.97

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'
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'

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

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

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

_cell_length_a                   7.1811(3)
_cell_length_b                   26.8955(13)
_cell_length_c                   13.1818(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.643(5)
_cell_angle_gamma                90
_cell_volume                     2523.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2716
_cell_measurement_theta_min      3.4008
_cell_measurement_theta_max      29.4877

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_F_000             1292
_exptl_transmission_factor_min   0.659
_exptl_transmission_factor_max   0.860
_exptl_crystal_size_max          0.3800
_exptl_crystal_size_mid          0.1490
_exptl_crystal_size_min          0.0836
_exptl_absorpt_coefficient_mu    1.296
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_T_max  0.860
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_reflns_number            12228
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.408
_diffrn_reflns_theta_max         29.553
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5951
_reflns_number_gt                4003
_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, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0385P)²+0.9657P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5951
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
Cu1 Cu 0.36418(5) 0.45876(2) 0.40101(3) 0.02785(12) Uani 1 1 d . . . . .
Cl1 Cl 0.62099(11) 0.50969(3) 0.39696(6) 0.0350(2) Uani 1 1 d . . . . .
N1 N 0.5163(3) 0.39522(10) 0.4233(2) 0.0284(6) Uani 1 1 d . . . . .
C2 C 0.6184(4) 0.37213(12) 0.3598(2) 0.0267(7) Uani 1 1 d . . . . .
Cl2 Cl 0.10350(12) 0.41215(4) 0.40455(8) 0.0469(3) Uani 1 1 d . . . . .
N3 N 0.6691(3) 0.32622(10) 0.3949(2) 0.0273(6) Uani 1 1 d . . . . .
C4 C 0.5929(4) 0.32093(12) 0.4860(2) 0.0280(7) Uani 1 1 d . . . . .
C5 C 0.5007(4) 0.36315(12) 0.5019(3) 0.0291(7) Uani 1 1 d . . . . .
H5 H 0.4368 0.3695 0.5575 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7738(4) 0.28950(13) 0.3418(3) 0.0346(8) Uani 1 1 d . . . . .
H6A H 0.7614 0.2974 0.2694 0.041 Uiso 1 1 calc R U . . .
H6B H 0.7212 0.2567 0.3489 0.041 Uiso 1 1 calc R U . . .
C7 C 0.9814(4) 0.28938(13) 0.3860(3) 0.0356(8) Uani 1 1 d . . . . .
H7A H 0.9916 0.2829 0.4590 0.043 Uiso 1 1 calc R U . . .
H7B H 1.0330 0.3222 0.3771 0.043 Uiso 1 1 calc R U . . .
S8 S 1.11817(11) 0.24487(3) 0.32973(7) 0.0378(2) Uani 1 1 d . . . . .
O9 O 1.3070(3) 0.24929(11) 0.3798(2) 0.0601(8) Uani 1 1 d . . . . .
O10 O 1.0281(4) 0.19742(10) 0.3335(2) 0.0576(8) Uani 1 1 d . . . . .
C11 C 1.1143(5) 0.26167(16) 0.2008(3) 0.0514(11) Uani 1 1 d . . . . .
H11A H 1.1794 0.2363 0.1668 0.062 Uiso 1 1 calc R U . . .
H11B H 0.9848 0.2623 0.1686 0.062 Uiso 1 1 calc R U . . .
C12 C 1.2025(9) 0.3113(2) 0.1844(5) 0.0910(18) Uani 1 1 d . . . . .
H12A H 1.1995 0.3171 0.1123 0.137 Uiso 1 1 calc R U . . .
H12B H 1.3304 0.3113 0.2167 0.137 Uiso 1 1 calc R U . . .
H12C H 1.1338 0.3370 0.2135 0.137 Uiso 1 1 calc R U . . .
N13 N 0.6146(4) 0.27846(12) 0.5498(2) 0.0404(7) Uani 1 1 d . . . . .
O14 O 0.7127(4) 0.24373(10) 0.5279(2) 0.0521(7) Uani 1 1 d . . . . .
O15 O 0.5333(5) 0.27867(12) 0.6257(2) 0.0652(9) Uani 1 1 d . . . . .
C16 C 0.6628(5) 0.39329(15) 0.2623(3) 0.0410(9) Uani 1 1 d . . . . .
H16A H 0.7890 0.3846 0.2530 0.062 Uiso 1 1 calc R U . . .
H16B H 0.6511 0.4288 0.2640 0.062 Uiso 1 1 calc R U . . .
H16C H 0.5770 0.3802 0.2066 0.062 Uiso 1 1 calc R U . . .
N21 N 0.1942(3) 0.51209(10) 0.3366(2) 0.0292(6) Uani 1 1 d . . . . .
C22 C 0.0908(4) 0.51197(13) 0.2451(3) 0.0290(7) Uani 1 1 d . . . . .
N23 N -0.0192(3) 0.55298(10) 0.23459(19) 0.0255(6) Uani 1 1 d . . . . .
C24 C 0.0216(4) 0.57960(12) 0.3240(2) 0.0269(7) Uani 1 1 d . . . . .
C25 C 0.1515(4) 0.55428(13) 0.3864(3) 0.0308(8) Uani 1 1 d . . . . .
H25 H 0.2033 0.5638 0.4519 0.037 Uiso 1 1 calc R U . . .
C26 C -0.1354(4) 0.56888(13) 0.1404(2) 0.0299(7) Uani 1 1 d . . . . .
H26A H -0.0789 0.5575 0.0817 0.036 Uiso 1 1 calc R U . . .
H26B H -0.1403 0.6049 0.1381 0.036 Uiso 1 1 calc R U . . .
C27 C -0.3359(4) 0.54815(13) 0.1342(3) 0.0326(8) Uani 1 1 d . . . . .
H27A H -0.3800 0.5517 0.2003 0.039 Uiso 1 1 calc R U . . .
H27B H -0.3351 0.5130 0.1178 0.039 Uiso 1 1 calc R U . . .
S28 S -0.49129(12) 0.57967(4) 0.03988(7) 0.0380(2) Uani 1 1 d . . . . .
O29 O -0.3938(4) 0.58778(14) -0.04606(19) 0.0701(10) Uani 1 1 d . . . . .
O30 O -0.6646(4) 0.55228(11) 0.0243(2) 0.0627(8) Uani 1 1 d . . . . .
C31 C -0.5350(5) 0.63737(14) 0.0938(3) 0.0469(10) Uani 1 1 d . . . . .
H31A H -0.4159 0.6534 0.1168 0.056 Uiso 1 1 calc R U . . .
H31B H -0.6030 0.6582 0.0414 0.056 Uiso 1 1 calc R U . . .
C32 C -0.6468(6) 0.63354(19) 0.1830(4) 0.0675(14) Uani 1 1 d . . . . .
H32A H -0.6621 0.6661 0.2108 0.101 Uiso 1 1 calc R U . . .
H32B H -0.5813 0.6126 0.2349 0.101 Uiso 1 1 calc R U . . .
H32C H -0.7680 0.6195 0.1600 0.101 Uiso 1 1 calc R U . . .
N33 N -0.0701(4) 0.62408(11) 0.3462(2) 0.0303(6) Uani 1 1 d . . . . .
O34 O 0.0152(4) 0.65247(10) 0.4084(2) 0.0486(7) Uani 1 1 d . . . . .
O35 O -0.2302(3) 0.63176(9) 0.30309(19) 0.0385(6) Uani 1 1 d . . . . .
C36 C 0.0960(5) 0.47383(15) 0.1651(3) 0.0454(10) Uani 1 1 d . . . . .
H36A H -0.0297 0.4666 0.1341 0.068 Uiso 1 1 calc R U . . .
H36B H 0.1533 0.4441 0.1951 0.068 Uiso 1 1 calc R U . . .
H36C H 0.1678 0.4860 0.1138 0.068 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
Cu1 N21 1.998(3) . ?
Cu1 N1 2.028(3) . ?
Cu1 Cl2 2.2586(9) . ?
Cu1 Cl1 2.3036(9) . ?
N1 C2 1.336(4) . ?
N1 C5 1.365(4) . ?
C2 N3 1.351(4) . ?
C2 C16 1.479(5) . ?
N3 C4 1.392(4) . ?
N3 C6 1.473(4) . ?
C4 C5 1.345(4) . ?
C4 N13 1.415(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.527(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 S8 1.773(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
S8 O9 1.432(3) . ?
S8 O10 1.435(3) . ?
S8 C11 1.755(4) . ?
C11 C12 1.505(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N13 O15 1.224(4) . ?
N13 O14 1.227(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N21 C22 1.330(4) . ?
N21 C25 1.366(4) . ?
C22 N23 1.353(4) . ?
C22 C36 1.476(5) . ?
N23 C24 1.377(4) . ?
N23 C26 1.465(4) . ?
C24 C25 1.344(4) . ?
C24 N33 1.415(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.536(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 S28 1.772(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
S28 O29 1.426(3) . ?
S28 O30 1.437(3) . ?
S28 C31 1.752(4) . ?
C31 C32 1.514(5) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
N33 O34 1.224(4) . ?
N33 O35 1.230(3) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 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
N21 Cu1 N1 162.38(11) . . ?
N21 Cu1 Cl2 86.91(8) . . ?
N1 Cu1 Cl2 87.78(8) . . ?
N21 Cu1 Cl1 90.51(8) . . ?
N1 Cu1 Cl1 94.99(8) . . ?
Cl2 Cu1 Cl1 177.22(4) . . ?
C2 N1 C5 106.8(3) . . ?
C2 N1 Cu1 129.1(2) . . ?
C5 N1 Cu1 123.0(2) . . ?
N1 C2 N3 110.9(3) . . ?
N1 C2 C16 124.4(3) . . ?
N3 C2 C16 124.7(3) . . ?
C2 N3 C4 105.6(3) . . ?
C2 N3 C6 125.5(3) . . ?
C4 N3 C6 128.7(3) . . ?
C5 C4 N3 107.9(3) . . ?
C5 C4 N13 127.3(3) . . ?
N3 C4 N13 124.8(3) . . ?
C4 C5 N1 108.8(3) . . ?
C4 C5 H5 125.6 . . ?
N1 C5 H5 125.6 . . ?
N3 C6 C7 110.7(3) . . ?
N3 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 S8 114.1(2) . . ?
C6 C7 H7A 108.7 . . ?
S8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
S8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O9 S8 O10 117.49(19) . . ?
O9 S8 C11 108.46(19) . . ?
O10 S8 C11 108.28(19) . . ?
O9 S8 C7 107.14(16) . . ?
O10 S8 C7 107.97(16) . . ?
C11 S8 C7 107.05(19) . . ?
C12 C11 S8 114.5(3) . . ?
C12 C11 H11A 108.6 . . ?
S8 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
S8 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O15 N13 O14 123.2(3) . . ?
O15 N13 C4 117.1(3) . . ?
O14 N13 C4 119.7(3) . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 N21 C25 107.7(3) . . ?
C22 N21 Cu1 128.3(2) . . ?
C25 N21 Cu1 123.8(2) . . ?
N21 C22 N23 109.8(3) . . ?
N21 C22 C36 125.9(3) . . ?
N23 C22 C36 124.3(3) . . ?
C22 N23 C24 106.3(3) . . ?
C22 N23 C26 125.8(3) . . ?
C24 N23 C26 127.3(3) . . ?
C25 C24 N23 108.2(3) . . ?
C25 C24 N33 127.3(3) . . ?
N23 C24 N33 124.4(3) . . ?
C24 C25 N21 108.0(3) . . ?
C24 C25 H25 126.0 . . ?
N21 C25 H25 126.0 . . ?
N23 C26 C27 111.3(3) . . ?
N23 C26 H26A 109.4 . . ?
C27 C26 H26A 109.4 . . ?
N23 C26 H26B 109.4 . . ?
C27 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C26 C27 S28 111.2(2) . . ?
C26 C27 H27A 109.4 . . ?
S28 C27 H27A 109.4 . . ?
C26 C27 H27B 109.4 . . ?
S28 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
O29 S28 O30 118.2(2) . . ?
O29 S28 C31 108.7(2) . . ?
O30 S28 C31 108.28(18) . . ?
O29 S28 C27 107.51(17) . . ?
O30 S28 C27 107.91(17) . . ?
C31 S28 C27 105.61(18) . . ?
C32 C31 S28 113.4(3) . . ?
C32 C31 H31A 108.9 . . ?
S28 C31 H31A 108.9 . . ?
C32 C31 H31B 108.9 . . ?
S28 C31 H31B 108.9 . . ?
H31A C31 H31B 107.7 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O34 N33 O35 124.0(3) . . ?
O34 N33 C24 117.4(3) . . ?
O35 N33 C24 118.6(3) . . ?
C22 C36 H36A 109.5 . . ?
C22 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C22 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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
C5 N1 C2 N3 0.1(3) . . . . ?
Cu1 N1 C2 N3 -168.3(2) . . . . ?
C5 N1 C2 C16 177.6(3) . . . . ?
Cu1 N1 C2 C16 9.2(5) . . . . ?
N1 C2 N3 C4 -0.1(3) . . . . ?
C16 C2 N3 C4 -177.6(3) . . . . ?
N1 C2 N3 C6 176.6(3) . . . . ?
C16 C2 N3 C6 -0.9(5) . . . . ?
C2 N3 C4 C5 0.0(3) . . . . ?
C6 N3 C4 C5 -176.5(3) . . . . ?
C2 N3 C4 N13 -178.8(3) . . . . ?
C6 N3 C4 N13 4.7(5) . . . . ?
N3 C4 C5 N1 0.0(4) . . . . ?
N13 C4 C5 N1 178.8(3) . . . . ?
C2 N1 C5 C4 0.0(4) . . . . ?
Cu1 N1 C5 C4 169.2(2) . . . . ?
C2 N3 C6 C7 100.0(4) . . . . ?
C4 N3 C6 C7 -84.1(4) . . . . ?
N3 C6 C7 S8 178.1(2) . . . . ?
C6 C7 S8 O9 -179.6(3) . . . . ?
C6 C7 S8 O10 -52.2(3) . . . . ?
C6 C7 S8 C11 64.2(3) . . . . ?
O9 S8 C11 C12 -52.1(4) . . . . ?
O10 S8 C11 C12 179.3(3) . . . . ?
C7 S8 C11 C12 63.2(4) . . . . ?
C5 C4 N13 O15 4.0(5) . . . . ?
N3 C4 N13 O15 -177.4(3) . . . . ?
C5 C4 N13 O14 -175.6(3) . . . . ?
N3 C4 N13 O14 2.9(5) . . . . ?
C25 N21 C22 N23 -0.4(4) . . . . ?
Cu1 N21 C22 N23 173.7(2) . . . . ?
C25 N21 C22 C36 178.3(3) . . . . ?
Cu1 N21 C22 C36 -7.5(5) . . . . ?
N21 C22 N23 C24 0.8(3) . . . . ?
C36 C22 N23 C24 -178.0(3) . . . . ?
N21 C22 N23 C26 172.3(3) . . . . ?
C36 C22 N23 C26 -6.5(5) . . . . ?
C22 N23 C24 C25 -0.8(3) . . . . ?
C26 N23 C24 C25 -172.1(3) . . . . ?
C22 N23 C24 N33 -176.8(3) . . . . ?
C26 N23 C24 N33 11.9(5) . . . . ?
N23 C24 C25 N21 0.5(4) . . . . ?
N33 C24 C25 N21 176.4(3) . . . . ?
C22 N21 C25 C24 -0.1(4) . . . . ?
Cu1 N21 C25 C24 -174.6(2) . . . . ?
C22 N23 C26 C27 92.1(4) . . . . ?
C24 N23 C26 C27 -98.2(4) . . . . ?
N23 C26 C27 S28 164.7(2) . . . . ?
C26 C27 S28 O29 40.3(3) . . . . ?
C26 C27 S28 O30 168.8(2) . . . . ?
C26 C27 S28 C31 -75.6(3) . . . . ?
O29 S28 C31 C32 177.2(3) . . . . ?
O30 S28 C31 C32 47.7(3) . . . . ?
C27 S28 C31 C32 -67.7(3) . . . . ?
C25 C24 N33 O34 28.9(5) . . . . ?
N23 C24 N33 O34 -155.9(3) . . . . ?
C25 C24 N33 O35 -150.5(3) . . . . ?
N23 C24 N33 O35 24.8(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 O35 0.93 2.51 3.425(4) 167.3 3_566
C7 H7A O14 0.97 2.54 3.112(5) 118.0 .
C7 H7A O34 0.97 2.47 3.126(4) 124.7 3_666
C7 H7B Cl2 0.97 2.49 3.417(4) 160.1 1_655
C11 H11B O14 0.97 2.51 3.433(5) 158.2 4_565
C16 H16A Cl2 0.96 2.91 3.495(4) 120.7 1_655
C16 H16B Cl1 0.96 2.82 3.631(4) 142.8 .
C16 H16C O29 0.96 2.49 3.263(4) 137.3 3_565
C25 H25 Cl1 0.93 2.97 3.542(3) 121.4 3_666
C25 H25 N1 0.93 2.66 3.499(4) 149.7 3_666
C26 H26B O10 0.97 2.63 3.549(5) 158.9 2_655
C27 H27A Cl1 0.97 2.83 3.667(4) 145.3 1_455
C27 H27B O30 0.97 2.57 3.415(5) 146.1 3_465
C31 H31B O14 0.97 2.56 3.441(5) 151.1 2
C32 H32B O35 0.96 2.61 3.194(5) 119.3 .
C36 H36B Cl2 0.96 2.96 3.560(4) 121.9 .
C36 H36C O30 0.96 2.53 3.421(5) 154.4 1_655

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.082


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_rcr48
_database_code_depnum_ccdc_archive 'CCDC 1820834'
_audit_update_record             
;
2018-01-31 deposited with the CCDC.
2018-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        compound_3
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H26 Co N8 O14 S2'
_chemical_formula_sum            'C16 H26 Co N8 O14 S2'
_chemical_formula_weight         677.50

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'
Co Co 0.3494 0.9721 '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                   20.903(4)
_cell_length_b                   6.522(2)
_cell_length_c                   21.396(10)
_cell_angle_alpha                90
_cell_angle_beta                 113.45(2)
_cell_angle_gamma                90
_cell_volume                     2675.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2716
_cell_measurement_theta_min      3.458
_cell_measurement_theta_max      29.519

_exptl_crystal_description       prism
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_F_000             1396
_exptl_transmission_factor_min   0.426
_exptl_transmission_factor_max   0.835
_exptl_crystal_size_max          0.4710
_exptl_crystal_size_mid          0.3528
_exptl_crystal_size_min          0.2950
_exptl_absorpt_coefficient_mu    0.880
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.426
_exptl_absorpt_correction_T_max  0.835
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_reflns_number            19417
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.458
_diffrn_reflns_theta_max         29.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6549
_reflns_number_gt                4877
_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, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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)+(0.0262P)²+0.5566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6549
_refine_ls_number_parameters     374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
Co1 Co 0.98954(2) 0.15214(5) 0.74231(2) 0.02918(11) Uani 1 1 d . . . . .
S1 S 1.10708(4) 0.99653(9) 0.52898(3) 0.03458(16) Uani 1 1 d . . . . .
S2 S 0.89344(4) 1.04509(9) 0.95850(4) 0.03616(17) Uani 1 1 d . . . . .
N93 N 0.91530(10) 0.5576(3) 0.85326(10) 0.0274(4) Uani 1 1 d . . . . .
N95 N 1.08156(10) 0.5238(3) 0.63941(10) 0.0271(4) Uani 1 1 d . . . . .
O1 O 1.05192(9) 0.9260(3) 0.46760(9) 0.0433(5) Uani 1 1 d . . . . .
N96 N 1.04906(10) 0.3346(3) 0.70712(11) 0.0301(5) Uani 1 1 d . . . . .
N94 N 0.94166(10) 0.3572(3) 0.78342(11) 0.0307(5) Uani 1 1 d . . . . .
O2 O 0.93496(10) 0.9568(3) 1.02319(10) 0.0463(5) Uani 1 1 d . . . . .
O3 O 0.77791(10) 0.6279(3) 0.84281(11) 0.0522(5) Uani 1 1 d . . . . .
O4 O 1.21938(10) 0.5542(3) 0.64732(11) 0.0474(5) Uani 1 1 d . . . . .
C5 C 0.96700(12) 0.4681(3) 0.84091(13) 0.0275(5) Uani 1 1 d . . . . .
C94 C 1.07552(13) 0.6492(3) 0.57991(12) 0.0305(5) Uani 1 1 d . . . . .
H94A H 1.0274 0.6484 0.5472 0.037 Uiso 1 1 calc R U . . .
H94B H 1.1038 0.5884 0.5582 0.037 Uiso 1 1 calc R U . . .
C6 C 1.02747(12) 0.4630(3) 0.65424(13) 0.0278(5) Uani 1 1 d . . . . .
C7 C 1.09873(13) 0.8702(3) 0.59921(13) 0.0300(5) Uani 1 1 d . . . . .
H7A H 1.1431 0.8722 0.6382 0.036 Uiso 1 1 calc R U . . .
H7B H 1.0647 0.9414 0.6116 0.036 Uiso 1 1 calc R U . . .
N97 N 1.20913(11) 0.4531(3) 0.69049(13) 0.0386(5) Uani 1 1 d . . . . .
C9 C 0.92354(13) 0.6831(3) 0.91286(12) 0.0297(5) Uani 1 1 d . . . . .
H9A H 0.9707 0.6680 0.9470 0.036 Uiso 1 1 calc R U . . .
H9B H 0.8917 0.6347 0.9324 0.036 Uiso 1 1 calc R U . . .
O95 O 1.04744(12) -0.1141(3) 0.72612(12) 0.0525(5) Uani 1 1 d . . . . .
O96 O 1.07185(11) 0.0231(3) 0.82387(10) 0.0529(5) Uani 1 1 d . . . . .
O97 O 0.89943(11) 0.0799(3) 0.65606(10) 0.0523(5) Uani 1 1 d . . . . .
O6 O 0.91618(12) -0.0980(3) 0.74496(13) 0.0549(6) Uani 1 1 d . . . . .
N98 N 1.08411(14) -0.1197(3) 0.78865(16) 0.0480(6) Uani 1 1 d . . . . .
N4 N 0.78626(11) 0.5506(3) 0.79434(13) 0.0436(6) Uani 1 1 d . . . . .
C99 C 0.85412(12) 0.4999(4) 0.80008(13) 0.0318(6) Uani 1 1 d . . . . .
C95 C 0.90920(13) 0.9085(3) 0.89411(13) 0.0305(5) Uani 1 1 d . . . . .
H95A H 0.8689 0.9205 0.8513 0.037 Uiso 1 1 calc R U . . .
H95B H 0.9489 0.9682 0.8882 0.037 Uiso 1 1 calc R U . . .
C11 C 1.11961(13) 0.3157(4) 0.72758(13) 0.0332(6) Uani 1 1 d . . . . .
H11 H 1.1488 0.2366 0.7639 0.040 Uiso 1 1 calc R U . . .
C96 C 1.13986(12) 0.4304(3) 0.68648(13) 0.0304(5) Uani 1 1 d . . . . .
C12 C 0.87100(13) 0.3796(4) 0.75829(14) 0.0352(6) Uani 1 1 d . . . . .
H12 H 0.8395 0.3205 0.7183 0.042 Uiso 1 1 calc R U . . .
N99 N 0.88068(13) -0.0717(4) 0.68283(16) 0.0497(7) Uani 1 1 d . . . . .
O93 O 1.11220(12) 1.2126(3) 0.54268(11) 0.0593(6) Uani 1 1 d . . . . .
C14 C 0.95457(13) 0.5294(4) 0.61757(15) 0.0403(6) Uani 1 1 d . . . . .
H14A H 0.9292 0.5067 0.6457 0.061 Uiso 1 1 calc R U . . .
H14B H 0.9335 0.4520 0.5762 0.061 Uiso 1 1 calc R U . . .
H14C H 0.9535 0.6726 0.6069 0.061 Uiso 1 1 calc R U . . .
O92 O 1.25533(10) 0.3694(4) 0.73865(13) 0.0663(7) Uani 1 1 d . . . . .
O98 O 0.83223(12) -0.1804(4) 0.64887(15) 0.0833(8) Uani 1 1 d . . . . .
C17 C 1.04178(13) 0.4862(4) 0.88517(15) 0.0420(7) Uani 1 1 d . . . . .
H17A H 1.0690 0.4393 0.8610 0.063 Uiso 1 1 calc R U . . .
H17B H 1.0521 0.4041 0.9253 0.063 Uiso 1 1 calc R U . . .
H17C H 1.0528 0.6269 0.8981 0.063 Uiso 1 1 calc R U . . .
O99 O 0.73832(11) 0.5118(4) 0.73996(13) 0.0762(8) Uani 1 1 d . . . . .
O94 O 1.12811(13) -0.2490(3) 0.81588(15) 0.0802(8) Uani 1 1 d . . . . .
C20 C 1.18645(14) 0.9107(5) 0.52749(16) 0.0485(7) Uani 1 1 d . . . . .
H20A H 1.1865 0.7619 0.5273 0.058 Uiso 1 1 calc R U . . .
H20B H 1.1890 0.9562 0.4854 0.058 Uiso 1 1 calc R U . . .
C22 C 1.25013(17) 0.9837(6) 0.58601(19) 0.0763(11) Uani 1 1 d . . . . .
H22A H 1.2910 0.9325 0.5812 0.114 Uiso 1 1 calc R U . . .
H22B H 1.2492 0.9345 0.6279 0.114 Uiso 1 1 calc R U . . .
H22C H 1.2510 1.1308 0.5864 0.114 Uiso 1 1 calc R U . . .
O91 O 0.90354(13) 1.2584(3) 0.94976(12) 0.0657(6) Uani 1 1 d . . . . .
C89 C 0.80412(15) 1.0030(5) 0.94170(18) 0.0606(9) Uani 1 1 d . . . . .
H89A H 0.7753 1.0568 0.8971 0.073 Uiso 1 1 calc R U . . .
H89B H 0.7954 0.8569 0.9416 0.073 Uiso 1 1 calc R U . . .
C88 C 0.7850(2) 1.1066(7) 0.9951(2) 0.0916(13) Uani 1 1 d . . . . .
H88A H 0.7357 1.0952 0.9826 0.137 Uiso 1 1 calc R U . . .
H88B H 0.7978 1.2488 0.9981 0.137 Uiso 1 1 calc R U . . .
H88C H 0.8094 1.0417 1.0384 0.137 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
Co1 N94 2.0651(19) . ?
Co1 N96 2.0679(19) . ?
Co1 O96 2.079(2) . ?
Co1 O97 2.099(2) . ?
Co1 O95 2.2211(19) . ?
Co1 O6 2.255(2) . ?
S1 O93 1.4345(18) . ?
S1 O1 1.435(2) . ?
S1 C20 1.763(3) . ?
S1 C7 1.782(2) . ?
S2 O2 1.430(2) . ?
S2 O91 1.4308(19) . ?
S2 C89 1.777(3) . ?
S2 C95 1.778(2) . ?
N93 C5 1.344(3) . ?
N93 C99 1.383(3) . ?
N93 C9 1.467(3) . ?
N95 C6 1.350(3) . ?
N95 C96 1.376(3) . ?
N95 C94 1.476(3) . ?
N96 C6 1.334(3) . ?
N96 C11 1.367(3) . ?
N94 C5 1.341(3) . ?
N94 C12 1.364(3) . ?
O3 N4 1.226(3) . ?
O4 N97 1.221(3) . ?
C5 C17 1.475(3) . ?
C94 C7 1.524(3) . ?
C6 C14 1.474(3) . ?
N97 O92 1.225(3) . ?
N97 C96 1.424(3) . ?
C9 C95 1.522(3) . ?
O95 N98 1.250(3) . ?
O96 N98 1.287(3) . ?
O97 N99 1.280(3) . ?
O6 N99 1.250(3) . ?
N98 O94 1.212(3) . ?
N4 O99 1.222(3) . ?
N4 C99 1.414(3) . ?
C99 C12 1.338(3) . ?
C11 C96 1.345(3) . ?
N99 O98 1.213(3) . ?
C20 C22 1.497(4) . ?
C89 C88 1.511(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
N94 Co1 N96 104.26(8) . . ?
N94 Co1 O96 106.50(8) . . ?
N96 Co1 O96 96.99(8) . . ?
N94 Co1 O97 95.88(8) . . ?
N96 Co1 O97 105.57(8) . . ?
O96 Co1 O97 143.13(9) . . ?
N94 Co1 O95 163.58(8) . . ?
N96 Co1 O95 87.06(7) . . ?
O96 Co1 O95 59.62(8) . . ?
O97 Co1 O95 92.38(8) . . ?
N94 Co1 O6 90.47(7) . . ?
N96 Co1 O6 159.90(8) . . ?
O96 Co1 O6 91.71(9) . . ?
O97 Co1 O6 58.58(8) . . ?
O95 Co1 O6 81.75(8) . . ?
O93 S1 O1 117.98(13) . . ?
O93 S1 C20 108.75(14) . . ?
O1 S1 C20 107.50(13) . . ?
O93 S1 C7 107.83(12) . . ?
O1 S1 C7 108.10(11) . . ?
C20 S1 C7 106.08(13) . . ?
O2 S2 O91 117.00(13) . . ?
O2 S2 C89 108.52(15) . . ?
O91 S2 C89 108.77(15) . . ?
O2 S2 C95 108.66(11) . . ?
O91 S2 C95 107.66(12) . . ?
C89 S2 C95 105.64(13) . . ?
C5 N93 C99 105.82(19) . . ?
C5 N93 C9 126.0(2) . . ?
C99 N93 C9 128.12(19) . . ?
C6 N95 C96 106.17(19) . . ?
C6 N95 C94 125.0(2) . . ?
C96 N95 C94 128.58(19) . . ?
C6 N96 C11 106.62(19) . . ?
C6 N96 Co1 128.37(16) . . ?
C11 N96 Co1 124.09(16) . . ?
C5 N94 C12 105.92(19) . . ?
C5 N94 Co1 131.20(16) . . ?
C12 N94 Co1 122.25(17) . . ?
N94 C5 N93 111.1(2) . . ?
N94 C5 C17 124.2(2) . . ?
N93 C5 C17 124.7(2) . . ?
N95 C94 C7 112.44(19) . . ?
N96 C6 N95 110.6(2) . . ?
N96 C6 C14 124.4(2) . . ?
N95 C6 C14 125.0(2) . . ?
C94 C7 S1 109.65(16) . . ?
O4 N97 O92 124.0(2) . . ?
O4 N97 C96 119.4(2) . . ?
O92 N97 C96 116.5(2) . . ?
N93 C9 C95 111.54(19) . . ?
N98 O95 Co1 89.78(15) . . ?
N98 O96 Co1 95.31(17) . . ?
N99 O97 Co1 96.17(18) . . ?
N99 O6 Co1 89.77(16) . . ?
O94 N98 O95 124.0(3) . . ?
O94 N98 O96 120.8(3) . . ?
O95 N98 O96 115.2(2) . . ?
O99 N4 O3 123.5(2) . . ?
O99 N4 C99 116.6(2) . . ?
O3 N4 C99 119.9(2) . . ?
C12 C99 N93 107.8(2) . . ?
C12 C99 N4 127.0(2) . . ?
N93 C99 N4 125.1(2) . . ?
C9 C95 S2 110.94(17) . . ?
C96 C11 N96 108.7(2) . . ?
C11 C96 N95 107.9(2) . . ?
C11 C96 N97 126.6(2) . . ?
N95 C96 N97 125.5(2) . . ?
C99 C12 N94 109.4(2) . . ?
O98 N99 O6 123.9(3) . . ?
O98 N99 O97 121.0(3) . . ?
O6 N99 O97 115.1(2) . . ?
C22 C20 S1 114.5(2) . . ?
C88 C89 S2 110.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N94 C5 N93 0.5(3) . . . . ?
Co1 N94 C5 N93 -170.33(15) . . . . ?
C12 N94 C5 C17 179.6(2) . . . . ?
Co1 N94 C5 C17 8.8(3) . . . . ?
C99 N93 C5 N94 -0.3(3) . . . . ?
C9 N93 C5 N94 177.4(2) . . . . ?
C99 N93 C5 C17 -179.4(2) . . . . ?
C9 N93 C5 C17 -1.7(4) . . . . ?
C6 N95 C94 C7 105.4(3) . . . . ?
C96 N95 C94 C7 -81.1(3) . . . . ?
C11 N96 C6 N95 1.1(3) . . . . ?
Co1 N96 C6 N95 -168.06(15) . . . . ?
C11 N96 C6 C14 -178.6(2) . . . . ?
Co1 N96 C6 C14 12.2(3) . . . . ?
C96 N95 C6 N96 -1.1(3) . . . . ?
C94 N95 C6 N96 173.62(19) . . . . ?
C96 N95 C6 C14 178.6(2) . . . . ?
C94 N95 C6 C14 -6.7(4) . . . . ?
N95 C94 C7 S1 168.12(16) . . . . ?
O93 S1 C7 C94 166.27(18) . . . . ?
O1 S1 C7 C94 37.7(2) . . . . ?
C20 S1 C7 C94 -77.4(2) . . . . ?
C5 N93 C9 C95 108.7(3) . . . . ?
C99 N93 C9 C95 -74.0(3) . . . . ?
Co1 O95 N98 O94 176.4(2) . . . . ?
Co1 O95 N98 O96 -3.0(2) . . . . ?
Co1 O96 N98 O94 -176.2(2) . . . . ?
Co1 O96 N98 O95 3.3(2) . . . . ?
C5 N93 C99 C12 0.0(3) . . . . ?
C9 N93 C99 C12 -177.7(2) . . . . ?
C5 N93 C99 N4 176.4(2) . . . . ?
C9 N93 C99 N4 -1.3(4) . . . . ?
O99 N4 C99 C12 -14.0(4) . . . . ?
O3 N4 C99 C12 165.4(3) . . . . ?
O99 N4 C99 N93 170.3(3) . . . . ?
O3 N4 C99 N93 -10.3(4) . . . . ?
N93 C9 C95 S2 162.44(16) . . . . ?
O2 S2 C95 C9 33.4(2) . . . . ?
O91 S2 C95 C9 161.03(18) . . . . ?
C89 S2 C95 C9 -82.9(2) . . . . ?
C6 N96 C11 C96 -0.8(3) . . . . ?
Co1 N96 C11 C96 169.01(16) . . . . ?
N96 C11 C96 N95 0.1(3) . . . . ?
N96 C11 C96 N97 180.0(2) . . . . ?
C6 N95 C96 C11 0.5(3) . . . . ?
C94 N95 C96 C11 -173.9(2) . . . . ?
C6 N95 C96 N97 -179.3(2) . . . . ?
C94 N95 C96 N97 6.3(4) . . . . ?
O4 N97 C96 C11 176.1(2) . . . . ?
O92 N97 C96 C11 -4.7(4) . . . . ?
O4 N97 C96 N95 -4.1(4) . . . . ?
O92 N97 C96 N95 175.2(2) . . . . ?
N93 C99 C12 N94 0.3(3) . . . . ?
N4 C99 C12 N94 -176.0(2) . . . . ?
C5 N94 C12 C99 -0.5(3) . . . . ?
Co1 N94 C12 C99 171.35(16) . . . . ?
Co1 O6 N99 O98 173.3(2) . . . . ?
Co1 O6 N99 O97 -5.9(2) . . . . ?
Co1 O97 N99 O98 -172.9(2) . . . . ?
Co1 O97 N99 O6 6.4(2) . . . . ?
O93 S1 C20 C22 47.2(3) . . . . ?
O1 S1 C20 C22 176.0(2) . . . . ?
C7 S1 C20 C22 -68.5(3) . . . . ?
O2 S2 C89 C88 61.7(3) . . . . ?
O91 S2 C89 C88 -66.6(3) . . . . ?
C95 S2 C89 C88 178.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C94 H94B O93 0.97 2.49 3.133(3) 123.7 1_545
C7 H7A O4 0.97 2.58 3.099(3) 114.0 .
C7 H7A O92 0.97 2.65 3.594(3) 166.0 2_756
C7 H7B O1 0.97 2.51 3.185(3) 127.0 3_776
C7 H7B O95 0.97 2.64 3.294(3) 125.1 1_565
C95 H95A O99 0.97 2.39 3.339(3) 166.3 2_656
C95 H95B O2 0.97 2.46 3.151(3) 127.7 3_777
C12 H12 O3 0.93 2.60 3.421(3) 147.6 2_646
C17 H17B O2 0.96 2.57 3.416(3) 147.5 3_767
C22 H22B O4 0.96 2.63 3.264(4) 123.8 .
C89 H89B O3 0.97 2.49 3.136(4) 123.6 .

_refine_diff_density_max         0.461
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.065


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_032XYZ16
_database_code_depnum_ccdc_archive 'CCDC 1820835'
_audit_update_record             
;
2018-01-31 deposited with the CCDC.
2018-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        compound_13
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H26 N8 O14 S2 Zn'
_chemical_formula_weight         683.94

_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                   20.7776(11)
_cell_length_b                   6.5108(4)
_cell_length_c                   21.3007(11)
_cell_angle_alpha                90
_cell_angle_beta                 114.0800(10)
_cell_angle_gamma                90
_cell_volume                     2630.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5261
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      27.23

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   0.7969
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.446
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    1.176
_shelx_estimated_absorpt_T_min   0.622
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4615
_exptl_absorpt_correction_T_max  0.8956
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-03'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            26676
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.094
_diffrn_reflns_theta_max         27.455
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6004
_reflns_number_gt                4451
_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       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_cell_refinement       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0323P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6004
_refine_ls_number_parameters     374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0736
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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
N1 N 0.58377(10) 0.4518(3) 0.14405(10) 0.0130(4) Uani 1 1 d . . . . .
Zn1 Zn 0.51004(2) 0.84154(4) 0.25806(2) 0.01474(9) Uani 1 1 d . . . . .
C2 C 0.53166(12) 0.5372(4) 0.15693(12) 0.0139(5) Uani 1 1 d . . . . .
N3 N 0.55801(10) 0.6519(3) 0.21419(10) 0.0150(4) Uani 1 1 d . . . . .
C4 C 0.62937(12) 0.6378(4) 0.23907(13) 0.0171(5) Uani 1 1 d . . . . .
H4 H 0.6613 0.7011 0.2787 0.021 Uiso 1 1 calc R U . . .
C5 C 0.64602(12) 0.5164(4) 0.19650(12) 0.0156(5) Uani 1 1 d . . . . .
C6 C 0.57496(12) 0.3227(4) 0.08462(12) 0.0140(5) Uani 1 1 d . . . . .
H6A H 0.6056 0.3726 0.0637 0.017 Uiso 1 1 calc R U . . .
H6B H 0.5267 0.3329 0.0507 0.017 Uiso 1 1 calc R U . . .
C7 C 0.59232(12) 0.0977(4) 0.10521(12) 0.0148(5) Uani 1 1 d . . . . .
H7A H 0.5535 0.0350 0.1123 0.018 Uiso 1 1 calc R U . . .
H7B H 0.6339 0.0902 0.1481 0.018 Uiso 1 1 calc R U . . .
S8 S 0.60751(3) -0.03869(9) 0.04055(3) 0.01673(14) Uani 1 1 d . . . . .
O9 O 0.56329(9) 0.0476(3) -0.02544(8) 0.0214(4) Uani 1 1 d . . . . .
O10 O 0.60001(10) -0.2555(3) 0.05044(10) 0.0289(5) Uani 1 1 d . . . . .
C11 C 0.69654(13) 0.0092(4) 0.05577(14) 0.0255(6) Uani 1 1 d . . . . .
H11A H 0.7038 0.1555 0.0530 0.031 Uiso 1 1 calc R U . . .
H11B H 0.7272 -0.0373 0.1015 0.031 Uiso 1 1 calc R U . . .
C12 C 0.71450(15) -0.1037(5) 0.00254(15) 0.0354(7) Uani 1 1 d . . . . .
H12A H 0.7633 -0.0826 0.0121 0.053 Uiso 1 1 calc R U . . .
H12B H 0.6858 -0.0520 -0.0425 0.053 Uiso 1 1 calc R U . . .
H12C H 0.7057 -0.2479 0.0044 0.053 Uiso 1 1 calc R U . . .
N13 N 0.71452(10) 0.4697(3) 0.20145(11) 0.0201(5) Uani 1 1 d . . . . .
O14 O 0.72197(9) 0.3836(3) 0.15356(9) 0.0238(4) Uani 1 1 d . . . . .
O15 O 0.76406(9) 0.5210(4) 0.25480(10) 0.0412(6) Uani 1 1 d . . . . .
C16 C 0.45525(12) 0.5126(4) 0.11298(13) 0.0204(6) Uani 1 1 d . . . . .
H16A H 0.4282 0.5721 0.1357 0.031 Uiso 1 1 calc R U . . .
H16B H 0.4442 0.3692 0.1051 0.031 Uiso 1 1 calc R U . . .
H16C H 0.4440 0.5805 0.0698 0.031 Uiso 1 1 calc R U . . .
N1A N 0.41840(10) 0.4816(3) 0.36250(10) 0.0133(4) Uani 1 1 d . . . . .
C2A C 0.47267(12) 0.5404(4) 0.34761(12) 0.0138(5) Uani 1 1 d . . . . .
N3A N 0.45082(10) 0.6693(3) 0.29395(10) 0.0151(4) Uani 1 1 d . . . . .
C4A C 0.37991(12) 0.6916(4) 0.27305(12) 0.0158(5) Uani 1 1 d . . . . .
H4A H 0.3507 0.7723 0.2365 0.019 Uiso 1 1 calc R U . . .
C5A C 0.35906(12) 0.5766(4) 0.31438(12) 0.0139(5) Uani 1 1 d . . . . .
C6A C 0.42477(12) 0.3547(3) 0.42170(12) 0.0144(5) Uani 1 1 d . . . . .
H6AA H 0.3973 0.4165 0.4442 0.017 Uiso 1 1 calc R U . . .
H6AB H 0.4737 0.3528 0.4545 0.017 Uiso 1 1 calc R U . . .
C7A C 0.39984(12) 0.1344(3) 0.40186(11) 0.0145(5) Uani 1 1 d . . . . .
H7AA H 0.4330 0.0622 0.3883 0.017 Uiso 1 1 calc R U . . .
H7AB H 0.3543 0.1348 0.3631 0.017 Uiso 1 1 calc R U . . .
S8A S 0.39309(3) 0.00609(9) 0.47261(3) 0.01596(14) Uani 1 1 d . . . . .
O9A O 0.45054(8) 0.0747(3) 0.53463(8) 0.0203(4) Uani 1 1 d . . . . .
O10A O 0.38639(10) -0.2110(3) 0.45806(9) 0.0274(4) Uani 1 1 d . . . . .
C11A C 0.31396(12) 0.0949(4) 0.47577(13) 0.0218(6) Uani 1 1 d . . . . .
H11C H 0.3119 0.0469 0.5180 0.026 Uiso 1 1 calc R U . . .
H11D H 0.3146 0.2439 0.4769 0.026 Uiso 1 1 calc R U . . .
C12A C 0.24815(13) 0.0242(5) 0.41524(15) 0.0354(8) Uani 1 1 d . . . . .
H12D H 0.2071 0.0700 0.4213 0.053 Uiso 1 1 calc R U . . .
H12E H 0.2479 -0.1230 0.4127 0.053 Uiso 1 1 calc R U . . .
H12F H 0.2478 0.0809 0.3735 0.053 Uiso 1 1 calc R U . . .
N13A N 0.28942(10) 0.5547(3) 0.31014(11) 0.0178(5) Uani 1 1 d . . . . .
O14A O 0.27912(9) 0.4529(3) 0.35375(9) 0.0223(4) Uani 1 1 d . . . . .
O15A O 0.24212(9) 0.6406(3) 0.26144(10) 0.0306(5) Uani 1 1 d . . . . .
C16A C 0.54697(12) 0.4727(4) 0.38496(13) 0.0193(5) Uani 1 1 d . . . . .
H16D H 0.5729 0.5025 0.3577 0.029 Uiso 1 1 calc R U . . .
H16E H 0.5481 0.3276 0.3933 0.029 Uiso 1 1 calc R U . . .
H16F H 0.5679 0.5443 0.4280 0.029 Uiso 1 1 calc R U . . .
N17 N 0.41684(11) 1.1334(3) 0.21348(12) 0.0221(5) Uani 1 1 d . . . . .
O18 O 0.43054(9) 0.9873(3) 0.17972(9) 0.0226(4) Uani 1 1 d . . . . .
O19 O 0.45176(9) 1.1332(3) 0.27755(9) 0.0254(4) Uani 1 1 d . . . . .
O20 O 0.37257(10) 1.2623(3) 0.18339(11) 0.0365(5) Uani 1 1 d . . . . .
N17A N 0.61857(11) 1.0939(3) 0.31705(12) 0.0221(5) Uani 1 1 d . . . . .
O18A O 0.59858(9) 0.9318(3) 0.33980(9) 0.0227(4) Uani 1 1 d . . . . .
O19A O 0.58527(10) 1.1349(3) 0.25510(10) 0.0302(5) Uani 1 1 d . . . . .
O20A O 0.66769(9) 1.1957(3) 0.35656(11) 0.0388(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.341(3) . ?
N1 C5 1.385(3) . ?
N1 C6 1.468(3) . ?
Zn1 N3A 2.031(2) . ?
Zn1 O18A 2.0364(17) . ?
Zn1 N3 2.037(2) . ?
Zn1 O18 2.0406(17) . ?
Zn1 O19 2.3783(18) . ?
Zn1 O19A 2.4850(19) . ?
C2 N3 1.342(3) . ?
C2 C16 1.486(3) . ?
N3 C4 1.359(3) . ?
C4 C5 1.350(3) . ?
C4 H4 0.9300 . ?
C5 N13 1.417(3) . ?
C6 C7 1.529(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 S8 1.772(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
S8 O9 1.4428(17) . ?
S8 O10 1.4452(18) . ?
S8 C11 1.771(3) . ?
C11 C12 1.520(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N13 O14 1.228(3) . ?
N13 O15 1.228(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1A C2A 1.345(3) . ?
N1A C5A 1.386(3) . ?
N1A C6A 1.468(3) . ?
C2A N3A 1.339(3) . ?
C2A C16A 1.486(3) . ?
N3A C4A 1.362(3) . ?
C4A C5A 1.355(3) . ?
C4A H4A 0.9300 . ?
C5A N13A 1.420(3) . ?
C6A C7A 1.525(3) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C7A S8A 1.778(2) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
S8A O10A 1.4414(18) . ?
S8A O9A 1.4433(17) . ?
S8A C11A 1.770(2) . ?
C11A C12A 1.518(3) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C12A H12D 0.9600 . ?
C12A H12E 0.9600 . ?
C12A H12F 0.9600 . ?
N13A O14A 1.229(3) . ?
N13A O15A 1.234(3) . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
N17 O20 1.217(3) . ?
N17 O19 1.257(3) . ?
N17 O18 1.293(3) . ?
N17A O20A 1.220(3) . ?
N17A O19A 1.244(3) . ?
N17A O18A 1.298(3) . ?

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
C2 N1 C5 105.98(19) . . ?
C2 N1 C6 125.93(19) . . ?
C5 N1 C6 128.05(19) . . ?
N3A Zn1 O18A 108.19(7) . . ?
N3A Zn1 N3 108.84(8) . . ?
O18A Zn1 N3 97.28(7) . . ?
N3A Zn1 O18 98.74(7) . . ?
O18A Zn1 O18 135.44(7) . . ?
N3 Zn1 O18 106.91(7) . . ?
N3A Zn1 O19 86.87(7) . . ?
O18A Zn1 O19 88.11(7) . . ?
N3 Zn1 O19 160.60(7) . . ?
O18 Zn1 O19 58.10(6) . . ?
N3A Zn1 O19A 156.64(7) . . ?
O18A Zn1 O19A 56.07(7) . . ?
N3 Zn1 O19A 91.35(7) . . ?
O18 Zn1 O19A 85.96(7) . . ?
O19 Zn1 O19A 76.17(6) . . ?
N1 C2 N3 110.65(19) . . ?
N1 C2 C16 124.8(2) . . ?
N3 C2 C16 124.6(2) . . ?
C2 N3 C4 107.0(2) . . ?
C2 N3 Zn1 131.28(15) . . ?
C4 N3 Zn1 121.48(16) . . ?
C5 C4 N3 108.4(2) . . ?
C5 C4 H4 125.8 . . ?
N3 C4 H4 125.8 . . ?
C4 C5 N1 108.0(2) . . ?
C4 C5 N13 126.9(2) . . ?
N1 C5 N13 125.0(2) . . ?
N1 C6 C7 111.68(19) . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 S8 110.68(17) . . ?
C6 C7 H7A 109.5 . . ?
S8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
S8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
O9 S8 O10 117.31(11) . . ?
O9 S8 C11 108.20(12) . . ?
O10 S8 C11 108.18(12) . . ?
O9 S8 C7 108.51(11) . . ?
O10 S8 C7 108.19(11) . . ?
C11 S8 C7 105.88(12) . . ?
C12 C11 S8 109.54(19) . . ?
C12 C11 H11A 109.8 . . ?
S8 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
S8 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O14 N13 O15 123.4(2) . . ?
O14 N13 C5 120.0(2) . . ?
O15 N13 C5 116.6(2) . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2A N1A C5A 106.09(19) . . ?
C2A N1A C6A 124.90(19) . . ?
C5A N1A C6A 128.9(2) . . ?
N3A C2A N1A 110.8(2) . . ?
N3A C2A C16A 124.0(2) . . ?
N1A C2A C16A 125.2(2) . . ?
C2A N3A C4A 106.9(2) . . ?
C2A N3A Zn1 128.38(16) . . ?
C4A N3A Zn1 123.98(16) . . ?
C5A C4A N3A 108.6(2) . . ?
C5A C4A H4A 125.7 . . ?
N3A C4A H4A 125.7 . . ?
C4A C5A N1A 107.7(2) . . ?
C4A C5A N13A 127.0(2) . . ?
N1A C5A N13A 125.3(2) . . ?
N1A C6A C7A 112.95(19) . . ?
N1A C6A H6AA 109.0 . . ?
C7A C6A H6AA 109.0 . . ?
N1A C6A H6AB 109.0 . . ?
C7A C6A H6AB 109.0 . . ?
H6AA C6A H6AB 107.8 . . ?
C6A C7A S8A 110.01(16) . . ?
C6A C7A H7AA 109.7 . . ?
S8A C7A H7AA 109.7 . . ?
C6A C7A H7AB 109.7 . . ?
S8A C7A H7AB 109.7 . . ?
H7AA C7A H7AB 108.2 . . ?
O10A S8A O9A 118.15(11) . . ?
O10A S8A C11A 108.60(12) . . ?
O9A S8A C11A 107.35(11) . . ?
O10A S8A C7A 108.20(11) . . ?
O9A S8A C7A 107.97(11) . . ?
C11A S8A C7A 105.94(12) . . ?
C12A C11A S8A 113.4(2) . . ?
C12A C11A H11C 108.9 . . ?
S8A C11A H11C 108.9 . . ?
C12A C11A H11D 108.9 . . ?
S8A C11A H11D 108.9 . . ?
H11C C11A H11D 107.7 . . ?
C11A C12A H12D 109.5 . . ?
C11A C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
C11A C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
O14A N13A O15A 123.7(2) . . ?
O14A N13A C5A 119.6(2) . . ?
O15A N13A C5A 116.7(2) . . ?
C2A C16A H16D 109.5 . . ?
C2A C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
C2A C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
O20 N17 O19 123.4(2) . . ?
O20 N17 O18 120.4(2) . . ?
O19 N17 O18 116.3(2) . . ?
N17 O18 Zn1 100.13(14) . . ?
N17 O19 Zn1 85.45(13) . . ?
O20A N17A O19A 124.2(2) . . ?
O20A N17A O18A 119.3(2) . . ?
O19A N17A O18A 116.5(2) . . ?
N17A O18A Zn1 103.32(14) . . ?
N17A O19A Zn1 83.77(14) . . ?

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
C5 N1 C2 N3 0.3(3) . . . . ?
C6 N1 C2 N3 -177.7(2) . . . . ?
C5 N1 C2 C16 178.9(2) . . . . ?
C6 N1 C2 C16 0.8(4) . . . . ?
N1 C2 N3 C4 -0.6(3) . . . . ?
C16 C2 N3 C4 -179.2(2) . . . . ?
N1 C2 N3 Zn1 173.82(16) . . . . ?
C16 C2 N3 Zn1 -4.8(4) . . . . ?
C2 N3 C4 C5 0.6(3) . . . . ?
Zn1 N3 C4 C5 -174.46(16) . . . . ?
N3 C4 C5 N1 -0.4(3) . . . . ?
N3 C4 C5 N13 176.6(2) . . . . ?
C2 N1 C5 C4 0.1(3) . . . . ?
C6 N1 C5 C4 178.1(2) . . . . ?
C2 N1 C5 N13 -177.0(2) . . . . ?
C6 N1 C5 N13 1.0(4) . . . . ?
C2 N1 C6 C7 -108.4(3) . . . . ?
C5 N1 C6 C7 74.0(3) . . . . ?
N1 C6 C7 S8 -162.26(15) . . . . ?
C6 C7 S8 O9 -32.73(19) . . . . ?
C6 C7 S8 O10 -160.99(16) . . . . ?
C6 C7 S8 C11 83.23(19) . . . . ?
O9 S8 C11 C12 -64.1(2) . . . . ?
O10 S8 C11 C12 63.9(2) . . . . ?
C7 S8 C11 C12 179.68(19) . . . . ?
C4 C5 N13 O14 -168.6(2) . . . . ?
N1 C5 N13 O14 7.9(4) . . . . ?
C4 C5 N13 O15 10.9(4) . . . . ?
N1 C5 N13 O15 -172.7(2) . . . . ?
C5A N1A C2A N3A 1.2(3) . . . . ?
C6A N1A C2A N3A -174.7(2) . . . . ?
C5A N1A C2A C16A -178.7(2) . . . . ?
C6A N1A C2A C16A 5.4(4) . . . . ?
N1A C2A N3A C4A -0.9(3) . . . . ?
C16A C2A N3A C4A 179.0(2) . . . . ?
N1A C2A N3A Zn1 169.41(15) . . . . ?
C16A C2A N3A Zn1 -10.7(3) . . . . ?
C2A N3A C4A C5A 0.2(3) . . . . ?
Zn1 N3A C4A C5A -170.60(16) . . . . ?
N3A C4A C5A N1A 0.5(3) . . . . ?
N3A C4A C5A N13A -179.5(2) . . . . ?
C2A N1A C5A C4A -1.0(3) . . . . ?
C6A N1A C5A C4A 174.7(2) . . . . ?
C2A N1A C5A N13A 178.9(2) . . . . ?
C6A N1A C5A N13A -5.4(4) . . . . ?
C2A N1A C6A C7A -105.5(3) . . . . ?
C5A N1A C6A C7A 79.6(3) . . . . ?
N1A C6A C7A S8A -168.76(16) . . . . ?
C6A C7A S8A O10A -166.24(16) . . . . ?
C6A C7A S8A O9A -37.29(19) . . . . ?
C6A C7A S8A C11A 77.45(19) . . . . ?
O10A S8A C11A C12A -48.1(2) . . . . ?
O9A S8A C11A C12A -176.87(19) . . . . ?
C7A S8A C11A C12A 68.0(2) . . . . ?
C4A C5A N13A O14A -176.2(2) . . . . ?
N1A C5A N13A O14A 3.9(4) . . . . ?
C4A C5A N13A O15A 4.2(4) . . . . ?
N1A C5A N13A O15A -175.7(2) . . . . ?
O20 N17 O18 Zn1 177.28(19) . . . . ?
O19 N17 O18 Zn1 -2.4(2) . . . . ?
O20 N17 O19 Zn1 -177.6(2) . . . . ?
O18 N17 O19 Zn1 2.00(19) . . . . ?
O20A N17A O18A Zn1 173.64(18) . . . . ?
O19A N17A O18A Zn1 -6.2(2) . . . . ?
O20A N17A O19A Zn1 -174.9(2) . . . . ?
O18A N17A O19A Zn1 5.00(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O14 0.93 2.55 3.401(3) 151.7 2_655
C4 H4 O18A 0.93 2.65 3.130(3) 112.6 .
C6 H6A O10 0.97 2.43 2.941(3) 112.1 1_565
C7 H7A O9 0.97 2.44 3.123(3) 127.5 3_655
C7 H7B O14 0.97 2.61 3.085(3) 110.1 .
C7 H7B O15 0.97 2.32 3.284(3) 171.0 2_645
C11 H11A O14 0.97 2.51 3.109(3) 120.2 .
C11 H11B O20A 0.97 2.65 3.363(3) 131.1 2_635
C16 H16C O9 0.96 2.58 3.353(3) 137.6 3_665
C6A H6AA O10A 0.97 2.46 3.120(3) 124.7 1_565
C7A H7AA O9A 0.97 2.47 3.149(3) 126.7 3_656
C7A H7AA O19 0.97 2.58 3.241(3) 125.1 1_545
C7A H7AB O14A 0.97 2.55 3.089(3) 115.0 .
C7A H7AB O15A 0.97 2.59 3.525(3) 161.9 2_545
C12A H12F O14A 0.96 2.59 3.257(3) 127.1 .

_refine_diff_density_max         0.513
_refine_diff_density_min         -1.219
_refine_diff_density_rms         0.131


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_030XYZ16
_database_code_depnum_ccdc_archive 'CCDC 1820836'
_audit_update_record             
;
2018-01-31 deposited with the CCDC.
2018-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        compound_9
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H13 Cu0.50 N4 O7 S'
_chemical_formula_sum            'C8 H13 Cu0.50 N4 O7 S'
_chemical_formula_weight         341.05

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'
Cu Cu 0.3201 1.2651 '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'
H H 0.0000 0.0000 '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                   7.2258(5)
_cell_length_b                   10.8229(8)
_cell_length_c                   16.4296(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.376(5)
_cell_angle_gamma                90
_cell_volume                     1284.83(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    837
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      21.15

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_F_000             702
_exptl_transmission_factor_min   0.6124
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.351
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.148
_exptl_absorpt_coefficient_mu    1.098
_shelx_estimated_absorpt_T_min   0.699
_shelx_estimated_absorpt_T_max   0.854
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.4398
_exptl_absorpt_correction_T_max  0.7112
_exptl_absorpt_process_details   '(Sheldrick, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-03'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            10970
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.253
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2953
_reflns_number_gt                2184
_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       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_cell_refinement       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0380P)²+0.6603P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2953
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_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
Cu1 Cu 1.0000 0.5000 0.5000 0.01408(16) Uani 1 2 d S . P . .
N1 N 0.7825(3) 0.3469(2) 0.28809(16) 0.0135(6) Uani 1 1 d . . . . .
C2 C 0.8157(4) 0.3460(3) 0.36930(19) 0.0132(6) Uani 1 1 d . . . . .
N3 N 0.8921(3) 0.4529(2) 0.39311(15) 0.0135(6) Uani 1 1 d . . . . .
C4 C 0.9060(4) 0.5254(3) 0.32494(19) 0.0162(7) Uani 1 1 d . . . . .
H4 H 0.9533 0.6053 0.3234 0.019 Uiso 1 1 calc R U . . .
C5 C 0.8394(4) 0.4615(3) 0.2601(2) 0.0162(7) Uani 1 1 d . . . . .
C6 C 0.6940(4) 0.2449(3) 0.2433(2) 0.0168(7) Uani 1 1 d . . . . .
H6A H 0.7411 0.1671 0.2641 0.020 Uiso 1 1 calc R U . . .
H6B H 0.7276 0.2505 0.1863 0.020 Uiso 1 1 calc R U . . .
C7 C 0.4839(4) 0.2453(3) 0.2499(2) 0.0171(7) Uani 1 1 d . . . . .
H7A H 0.4523 0.2607 0.3063 0.021 Uiso 1 1 calc R U . . .
H7B H 0.4395 0.1631 0.2364 0.021 Uiso 1 1 calc R U . . .
S8 S 0.36110(11) 0.35306(8) 0.18860(5) 0.0169(2) Uani 1 1 d . . . . .
O9 O 0.4407(3) 0.4744(2) 0.19872(15) 0.0231(6) Uani 1 1 d . . . . .
O10 O 0.1676(3) 0.3379(2) 0.20784(16) 0.0297(6) Uani 1 1 d . . . . .
C11 C 0.3966(5) 0.3042(3) 0.0870(2) 0.0215(7) Uani 1 1 d . . . . .
H11A H 0.5274 0.3075 0.0744 0.026 Uiso 1 1 calc R U . . .
H11B H 0.3551 0.2195 0.0806 0.026 Uiso 1 1 calc R U . . .
C12 C 0.2895(6) 0.3876(4) 0.0293(2) 0.0337(9) Uani 1 1 d . . . . .
H12A H 0.3060 0.3596 -0.0256 0.051 Uiso 1 1 calc R U . . .
H12B H 0.3343 0.4708 0.0343 0.051 Uiso 1 1 calc R U . . .
H12C H 0.1604 0.3852 0.0426 0.051 Uiso 1 1 calc R U . . .
N13 N 0.8510(3) 0.4978(3) 0.17697(17) 0.0185(6) Uani 1 1 d . . . . .
O14 O 0.8161(3) 0.4240(2) 0.12271(15) 0.0260(6) Uani 1 1 d . . . . .
O15 O 0.8994(4) 0.6054(2) 0.16520(16) 0.0329(6) Uani 1 1 d . . . . .
C16 C 0.7678(5) 0.2414(3) 0.4234(2) 0.0202(7) Uani 1 1 d . . . . .
H16A H 0.8554 0.2372 0.4675 0.030 Uiso 1 1 calc R U . . .
H16B H 0.7711 0.1657 0.3930 0.030 Uiso 1 1 calc R U . . .
H16C H 0.6458 0.2536 0.4448 0.030 Uiso 1 1 calc R U . . .
N17 N 0.6761(4) 0.5153(3) 0.57381(17) 0.0184(6) Uani 1 1 d . . . . .
O18 O 0.7886(3) 0.4243(2) 0.56032(14) 0.0198(5) Uani 1 1 d . . . . .
O19 O 0.7203(3) 0.6196(2) 0.54928(16) 0.0291(6) Uani 1 1 d . . . . .
O20 O 0.5329(3) 0.4947(2) 0.61109(17) 0.0333(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 1.983(3) 3_766 ?
Cu1 N3 1.983(3) . ?
Cu1 O18 2.002(2) . ?
Cu1 O18 2.002(2) 3_766 ?
Cu1 O19 2.537(3) . ?
N1 C2 1.354(4) . ?
N1 C5 1.386(4) . ?
N1 C6 1.471(4) . ?
C2 N3 1.340(4) . ?
C2 C16 1.481(4) . ?
N3 C4 1.371(4) . ?
C4 C5 1.355(4) . ?
C4 H4 0.9300 . ?
C5 N13 1.425(4) . ?
C6 C7 1.523(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 S8 1.775(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
S8 O9 1.443(2) . ?
S8 O10 1.445(2) . ?
S8 C11 1.771(3) . ?
C11 C12 1.518(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N13 O14 1.222(4) . ?
N13 O15 1.232(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N17 O20 1.226(3) . ?
N17 O19 1.241(4) . ?
N17 O18 1.297(3) . ?

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
N3 Cu1 N3 180.0 3_766 . ?
N3 Cu1 O18 87.92(10) 3_766 . ?
N3 Cu1 O18 92.09(10) . . ?
N3 Cu1 O18 92.08(10) 3_766 3_766 ?
N3 Cu1 O18 87.91(10) . 3_766 ?
O18 Cu1 O18 180.0 . 3_766 ?
N3 Cu1 O19 84.01(9) 3_766 . ?
N3 Cu1 O19 95.99(9) . . ?
O18 Cu1 O19 55.86(9) . . ?
O18 Cu1 O19 124.14(9) 3_766 . ?
C2 N1 C5 106.4(3) . . ?
C2 N1 C6 124.1(3) . . ?
C5 N1 C6 129.4(3) . . ?
N3 C2 N1 110.6(3) . . ?
N3 C2 C16 125.6(3) . . ?
N1 C2 C16 123.8(3) . . ?
C2 N3 C4 106.7(3) . . ?
C2 N3 Cu1 129.7(2) . . ?
C4 N3 Cu1 123.1(2) . . ?
C5 C4 N3 108.8(3) . . ?
C5 C4 H4 125.6 . . ?
N3 C4 H4 125.6 . . ?
C4 C5 N1 107.5(3) . . ?
C4 C5 N13 126.2(3) . . ?
N1 C5 N13 125.7(3) . . ?
N1 C6 C7 113.1(3) . . ?
N1 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
N1 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 S8 117.1(2) . . ?
C6 C7 H7A 108.0 . . ?
S8 C7 H7A 108.0 . . ?
C6 C7 H7B 108.0 . . ?
S8 C7 H7B 108.0 . . ?
H7A C7 H7B 107.3 . . ?
O9 S8 O10 117.63(15) . . ?
O9 S8 C11 108.69(16) . . ?
O10 S8 C11 108.58(16) . . ?
O9 S8 C7 109.60(15) . . ?
O10 S8 C7 106.38(15) . . ?
C11 S8 C7 105.28(16) . . ?
C12 C11 S8 109.6(2) . . ?
C12 C11 H11A 109.8 . . ?
S8 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
S8 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O14 N13 O15 124.1(3) . . ?
O14 N13 C5 120.4(3) . . ?
O15 N13 C5 115.5(3) . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O20 N17 O19 123.2(3) . . ?
O20 N17 O18 118.6(3) . . ?
O19 N17 O18 118.2(3) . . ?
N17 O18 Cu1 104.77(19) . . ?
N17 O19 Cu1 81.18(18) . . ?

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
C5 N1 C2 N3 -0.7(3) . . . . ?
C6 N1 C2 N3 -178.0(3) . . . . ?
C5 N1 C2 C16 177.6(3) . . . . ?
C6 N1 C2 C16 0.3(4) . . . . ?
N1 C2 N3 C4 0.8(3) . . . . ?
C16 C2 N3 C4 -177.5(3) . . . . ?
N1 C2 N3 Cu1 -171.54(19) . . . . ?
C16 C2 N3 Cu1 10.2(4) . . . . ?
C2 N3 C4 C5 -0.5(3) . . . . ?
Cu1 N3 C4 C5 172.4(2) . . . . ?
N3 C4 C5 N1 0.1(3) . . . . ?
N3 C4 C5 N13 -171.4(3) . . . . ?
C2 N1 C5 C4 0.4(3) . . . . ?
C6 N1 C5 C4 177.5(3) . . . . ?
C2 N1 C5 N13 171.9(3) . . . . ?
C6 N1 C5 N13 -11.0(5) . . . . ?
C2 N1 C6 C7 80.9(4) . . . . ?
C5 N1 C6 C7 -95.7(4) . . . . ?
N1 C6 C7 S8 77.7(3) . . . . ?
C6 C7 S8 O9 -50.0(3) . . . . ?
C6 C7 S8 O10 -178.1(2) . . . . ?
C6 C7 S8 C11 66.8(3) . . . . ?
O9 S8 C11 C12 -65.1(3) . . . . ?
O10 S8 C11 C12 63.9(3) . . . . ?
C7 S8 C11 C12 177.5(3) . . . . ?
C4 C5 N13 O14 167.0(3) . . . . ?
N1 C5 N13 O14 -3.0(5) . . . . ?
C4 C5 N13 O15 -12.2(4) . . . . ?
N1 C5 N13 O15 177.8(3) . . . . ?
O20 N17 O18 Cu1 -179.4(2) . . . . ?
O19 N17 O18 Cu1 -0.5(3) . . . . ?
O20 N17 O19 Cu1 179.3(3) . . . . ?
O18 N17 O19 Cu1 0.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6A O9 0.97 2.54 3.231(4) 128.1 2_645
C6 H6B O14 0.97 2.24 2.912(4) 125.2 .
C7 H7B O9 0.97 2.46 3.098(4) 123.2 2_645
C11 H11A O14 0.97 2.56 3.345(4) 138.2 .
C11 H11B O19 0.97 2.45 3.113(4) 125.3 2_645
C12 H12A O19 0.96 2.63 3.175(5) 116.2 2_645
C16 H16B O15 0.96 2.65 3.181(4) 115.0 2_745

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.102


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
