# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1857654'
_audit_update_record             
;
2019-01-03 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 N3 Na O5 S'
_chemical_formula_sum            'C10 H10 N3 Na O5 S'
_chemical_formula_weight         307.26

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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                   5.9967(9)
_cell_length_b                   28.244(5)
_cell_length_c                   7.6942(12)
_cell_angle_alpha                90
_cell_angle_beta                 111.292(5)
_cell_angle_gamma                90
_cell_volume                     1214.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6718
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      26.01

_exptl_crystal_description       PLATE
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.326
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16006
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.187
_diffrn_reflns_theta_max         26.048
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             2273
_reflns_number_gt                1882
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury CSD 3.10.3'
_computing_publication_material  
'SHELXL-2018/1 (Sheldrick, 2018), WinGX (Farrugia, 2012)'
_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)+(0.0286P)²+1.4270P] 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         2273
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
S1 S 0.72012(10) 0.05738(2) 0.85124(8) 0.01746(16) Uani 1 1 d . . . . .
O1 O 0.7042(3) 0.05085(6) 1.0334(2) 0.0255(4) Uani 1 1 d . . . . .
O2 O 0.5601(3) 0.02574(6) 0.7114(2) 0.0242(4) Uani 1 1 d . . . . .
O3 O 0.9620(3) 0.05588(6) 0.8524(2) 0.0226(4) Uani 1 1 d . . . . .
O4 O 1.0358(3) 0.05301(5) 0.4680(2) 0.0200(4) Uani 1 1 d . . . . .
N1 N 0.8089(4) 0.12182(7) 0.5567(3) 0.0181(4) Uani 1 1 d . . . . .
O5 O 1.1971(3) 0.15968(6) 0.1536(3) 0.0312(5) Uani 1 1 d . . . . .
N2 N 0.8631(3) 0.14748(7) 0.4352(3) 0.0178(4) Uani 1 1 d . . . . .
C9 C 1.0044(4) 0.13149(8) 0.3529(3) 0.0172(5) Uani 1 1 d . . . . .
N3 N 1.2720(4) 0.07289(8) 0.3094(3) 0.0217(5) Uani 1 1 d . . . . .
C1 C 0.6106(4) 0.11572(8) 0.7814(3) 0.0165(5) Uani 1 1 d . . . . .
C10 C 1.1085(4) 0.08296(8) 0.3801(3) 0.0168(5) Uani 1 1 d . . . . .
C6 C 0.6638(4) 0.14163(8) 0.6458(3) 0.0166(5) Uani 1 1 d . . . . .
C3 C 0.3642(4) 0.18033(8) 0.8133(3) 0.0229(6) Uani 1 1 d . . . . .
H3 H 0.261503 0.192990 0.867212 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5708(4) 0.18716(8) 0.5999(3) 0.0190(5) Uani 1 1 d . . . . .
H5 H 0.608444 0.204744 0.512073 0.023 Uiso 1 1 calc R U . . .
C2 C 0.4589(4) 0.13545(8) 0.8619(3) 0.0210(5) Uani 1 1 d . . . . .
H2 H 0.420418 0.118191 0.950063 0.025 Uiso 1 1 calc R U . . .
C8 C 1.0510(4) 0.16675(8) 0.2277(3) 0.0203(5) Uani 1 1 d . . . . .
C7 C 0.9165(5) 0.21264(8) 0.1956(4) 0.0265(6) Uani 1 1 d . . . . .
H7A H 0.978980 0.232029 0.305187 0.040 Uiso 1 1 calc R U . . .
H7B H 0.750012 0.206443 0.169357 0.040 Uiso 1 1 calc R U . . .
H7C H 0.934304 0.228842 0.091736 0.040 Uiso 1 1 calc R U . . .
C4 C 0.4238(4) 0.20624(8) 0.6833(3) 0.0215(5) Uani 1 1 d . . . . .
H4 H 0.363993 0.236728 0.652407 0.026 Uiso 1 1 calc R U . . .
Na1 Na 0.80624(16) -0.00717(3) 1.26017(12) 0.0207(2) Uani 1 1 d . . . . .
H2A H 1.329(5) 0.0446(11) 0.320(4) 0.031 Uiso 1 1 d . U . . .
H1 H 0.871(5) 0.0934(10) 0.585(4) 0.031 Uiso 1 1 d . U . . .
H2B H 1.309(5) 0.0937(10) 0.240(4) 0.031 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4477(17) . ?
S1 O1 1.4509(17) . ?
S1 O2 1.4585(17) . ?
S1 C1 1.783(2) . ?
S1 Na1 3.2778(12) 3_657 ?
O1 Na1 2.3084(18) . ?
O2 Na1 2.3446(19) 3_657 ?
O3 Na1 2.3343(18) 3_757 ?
O4 C10 1.256(3) . ?
O4 Na1 2.3471(18) 3_757 ?
O4 Na1 2.3963(19) 1_554 ?
N1 N2 1.313(3) . ?
N1 C6 1.405(3) . ?
N1 H1 0.88(3) . ?
O5 C8 1.223(3) . ?
N2 C9 1.309(3) . ?
C9 C8 1.481(3) . ?
C9 C10 1.489(3) . ?
N3 C10 1.314(3) . ?
N3 H2A 0.86(3) . ?
N3 H2B 0.87(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.402(3) . ?
C10 Na1 3.066(2) 1_554 ?
C6 C5 1.395(3) . ?
C3 C2 1.384(3) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C5 C4 1.375(3) . ?
C5 H5 0.9300 . ?
C2 H2 0.9300 . ?
C8 C7 1.499(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C4 H4 0.9300 . ?
Na1 Na1 3.5995(19) 3_758 ?

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
O3 S1 O1 114.06(10) . . ?
O3 S1 O2 112.09(10) . . ?
O1 S1 O2 112.22(10) . . ?
O3 S1 C1 106.70(10) . . ?
O1 S1 C1 105.22(10) . . ?
O2 S1 C1 105.79(10) . . ?
O3 S1 Na1 148.91(7) . 3_657 ?
O1 S1 Na1 78.62(8) . 3_657 ?
O2 S1 Na1 39.54(7) . 3_657 ?
C1 S1 Na1 96.12(8) . 3_657 ?
S1 O1 Na1 136.72(10) . . ?
S1 O2 Na1 117.13(10) . 3_657 ?
S1 O3 Na1 138.17(11) . 3_757 ?
C10 O4 Na1 138.14(15) . 3_757 ?
C10 O4 Na1 110.24(14) . 1_554 ?
Na1 O4 Na1 98.72(6) 3_757 1_554 ?
N2 N1 C6 118.99(19) . . ?
N2 N1 H1 119.2(18) . . ?
C6 N1 H1 121.7(18) . . ?
C9 N2 N1 121.68(19) . . ?
N2 C9 C8 113.03(19) . . ?
N2 C9 C10 124.2(2) . . ?
C8 C9 C10 122.79(19) . . ?
C10 N3 H2A 119.5(19) . . ?
C10 N3 H2B 120.0(18) . . ?
H2A N3 H2B 120(3) . . ?
C2 C1 C6 119.0(2) . . ?
C2 C1 S1 117.72(17) . . ?
C6 C1 S1 123.24(17) . . ?
O4 C10 N3 122.3(2) . . ?
O4 C10 C9 119.1(2) . . ?
N3 C10 C9 118.6(2) . . ?
O4 C10 Na1 47.16(11) . 1_554 ?
N3 C10 Na1 98.30(15) . 1_554 ?
C9 C10 Na1 123.37(15) . 1_554 ?
C5 C6 C1 119.4(2) . . ?
C5 C6 N1 120.3(2) . . ?
C1 C6 N1 120.2(2) . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
O5 C8 C9 122.0(2) . . ?
O5 C8 C7 119.9(2) . . ?
C9 C8 C7 118.1(2) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
O1 Na1 O3 99.68(7) . 3_757 ?
O1 Na1 O2 103.24(7) . 3_657 ?
O3 Na1 O2 127.37(7) 3_757 3_657 ?
O1 Na1 O4 167.30(7) . 3_757 ?
O3 Na1 O4 84.46(6) 3_757 3_757 ?
O2 Na1 O4 83.23(6) 3_657 3_757 ?
O1 Na1 O4 86.06(7) . 1_556 ?
O3 Na1 O4 112.99(7) 3_757 1_556 ?
O2 Na1 O4 115.28(7) 3_657 1_556 ?
O4 Na1 O4 81.28(6) 3_757 1_556 ?
O1 Na1 C10 66.65(7) . 1_556 ?
O3 Na1 C10 103.56(7) 3_757 1_556 ?
O2 Na1 C10 128.99(7) 3_657 1_556 ?
O4 Na1 C10 100.76(7) 3_757 1_556 ?
O4 Na1 C10 22.60(6) 1_556 1_556 ?
O1 Na1 S1 98.26(5) . 3_657 ?
O3 Na1 S1 107.13(5) 3_757 3_657 ?
O2 Na1 S1 23.33(4) 3_657 3_657 ?
O4 Na1 S1 91.90(5) 3_757 3_657 ?
O4 Na1 S1 138.30(5) 1_556 3_657 ?
C10 Na1 S1 147.75(5) 1_556 3_657 ?
O1 Na1 Na1 126.18(6) . 3_758 ?
O3 Na1 Na1 101.36(6) 3_757 3_758 ?
O2 Na1 Na1 101.97(6) 3_657 3_758 ?
O4 Na1 Na1 41.15(4) 3_757 3_758 ?
O4 Na1 Na1 40.13(4) 1_556 3_758 ?
C10 Na1 Na1 60.47(5) 1_556 3_758 ?
S1 Na1 Na1 121.24(4) 3_657 3_758 ?

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
O3 S1 O1 Na1 -60.08(18) . . . . ?
O2 S1 O1 Na1 68.76(18) . . . . ?
C1 S1 O1 Na1 -176.67(14) . . . . ?
Na1 S1 O1 Na1 90.01(15) 3_657 . . . ?
O3 S1 O2 Na1 163.79(9) . . . 3_657 ?
O1 S1 O2 Na1 33.92(13) . . . 3_657 ?
C1 S1 O2 Na1 -80.30(12) . . . 3_657 ?
O1 S1 O3 Na1 112.87(15) . . . 3_757 ?
O2 S1 O3 Na1 -16.04(18) . . . 3_757 ?
C1 S1 O3 Na1 -131.40(15) . . . 3_757 ?
Na1 S1 O3 Na1 4.1(3) 3_657 . . 3_757 ?
C6 N1 N2 C9 177.5(2) . . . . ?
N1 N2 C9 C8 -177.4(2) . . . . ?
N1 N2 C9 C10 2.7(3) . . . . ?
O3 S1 C1 C2 -144.67(19) . . . . ?
O1 S1 C1 C2 -23.2(2) . . . . ?
O2 S1 C1 C2 95.8(2) . . . . ?
Na1 S1 C1 C2 56.68(19) 3_657 . . . ?
O3 S1 C1 C6 37.5(2) . . . . ?
O1 S1 C1 C6 159.01(19) . . . . ?
O2 S1 C1 C6 -82.0(2) . . . . ?
Na1 S1 C1 C6 -121.16(19) 3_657 . . . ?
Na1 O4 C10 N3 61.5(3) 3_757 . . . ?
Na1 O4 C10 N3 -69.3(2) 1_554 . . . ?
Na1 O4 C10 C9 -119.1(2) 3_757 . . . ?
Na1 O4 C10 C9 110.05(19) 1_554 . . . ?
Na1 O4 C10 Na1 130.8(2) 3_757 . . 1_554 ?
N2 C9 C10 O4 9.4(3) . . . . ?
C8 C9 C10 O4 -170.4(2) . . . . ?
N2 C9 C10 N3 -171.3(2) . . . . ?
C8 C9 C10 N3 8.9(3) . . . . ?
N2 C9 C10 Na1 64.9(3) . . . 1_554 ?
C8 C9 C10 Na1 -114.9(2) . . . 1_554 ?
C2 C1 C6 C5 2.3(3) . . . . ?
S1 C1 C6 C5 -179.87(18) . . . . ?
C2 C1 C6 N1 -177.5(2) . . . . ?
S1 C1 C6 N1 0.4(3) . . . . ?
N2 N1 C6 C5 2.7(3) . . . . ?
N2 N1 C6 C1 -177.5(2) . . . . ?
C1 C6 C5 C4 -1.4(3) . . . . ?
N1 C6 C5 C4 178.4(2) . . . . ?
C4 C3 C2 C1 -0.7(4) . . . . ?
C6 C1 C2 C3 -1.3(4) . . . . ?
S1 C1 C2 C3 -179.21(19) . . . . ?
N2 C9 C8 O5 172.7(2) . . . . ?
C10 C9 C8 O5 -7.5(4) . . . . ?
N2 C9 C8 C7 -6.2(3) . . . . ?
C10 C9 C8 C7 173.7(2) . . . . ?
C6 C5 C4 C3 -0.6(4) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H2A O2 0.86(3) 2.14(3) 2.986(3) 169(3) 3_756 yes
N1 H1 O3 0.88(3) 2.20(3) 2.823(3) 128(2) . yes
N1 H1 O4 0.88(3) 1.93(3) 2.602(2) 132(2) . yes
N3 H2B O5 0.87(3) 2.01(3) 2.694(3) 134(2) . yes

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_compound4
_database_code_depnum_ccdc_archive 'CCDC 1857655'
_audit_update_record             
;
2019-01-03 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H32 N6 Na2 O18 S2'
_chemical_formula_sum            'C20 H32 N6 Na2 O18 S2'
_chemical_formula_weight         754.61

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'
Na Na 0.0362 0.0249 '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                   6.9078(3)
_cell_length_b                   27.7995(12)
_cell_length_c                   8.5286(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.458(2)
_cell_angle_gamma                90
_cell_volume                     1605.14(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8297
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      25.31

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.280
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20235
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.544
_diffrn_reflns_theta_max         25.368
_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             2943
_reflns_number_gt                2329
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury CSD 3.10.3'
_computing_publication_material  
'SHELXL-2018/3 (Sheldrick, 2018), WinGX (Farrugia, 2012)'
_refine_special_details          
'The oxygen atoms of the sulfonate group are disordered over two orientations and were refined with the use of PART instruction. The occupancy of O4, O5 and O6 refined to a ratio of 53%.'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0661P)²+1.2020P] 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         2943
_refine_ls_number_parameters     276
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.019
_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 0.2641(6) -0.03063(11) 0.9082(4) 0.0565(9) Uani 1 1 d . . . . .
H1A H 0.266388 -0.047056 1.007528 0.085 Uiso 1 1 calc R U . . .
H1B H 0.161471 -0.006795 0.892522 0.085 Uiso 1 1 calc R U . . .
H1C H 0.389200 -0.015308 0.910780 0.085 Uiso 1 1 calc R U . . .
C2 C 0.2253(4) -0.06602(8) 0.7737(3) 0.0315(5) Uani 1 1 d . . . . .
C3 C 0.2196(3) -0.04925(8) 0.6095(3) 0.0262(5) Uani 1 1 d . . . . .
C4 C 0.1731(3) -0.08139(8) 0.4674(3) 0.0286(5) Uani 1 1 d . . . . .
C5 C 0.3028(3) 0.06702(8) 0.4590(3) 0.0246(5) Uani 1 1 d . . . . .
C6 C 0.2858(3) 0.08734(8) 0.3068(3) 0.0287(5) Uani 1 1 d . . . . .
C7 C 0.3237(4) 0.13605(9) 0.2925(3) 0.0326(5) Uani 1 1 d . . . . .
H7 H 0.315474 0.149645 0.191726 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3738(4) 0.16439(9) 0.4280(3) 0.0311(5) Uani 1 1 d . . . . .
H8 H 0.396728 0.197118 0.418463 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3894(3) 0.14377(8) 0.5777(3) 0.0269(5) Uani 1 1 d . . . . .
C10 C 0.3561(3) 0.09509(8) 0.5942(3) 0.0268(5) Uani 1 1 d . . . . .
H10 H 0.369572 0.081442 0.695363 0.032 Uiso 1 1 calc R U . . .
N1 N 0.2606(3) 0.01764(7) 0.4633(2) 0.0282(4) Uani 1 1 d D . . . .
N2 N 0.2601(3) -0.00306(7) 0.6011(2) 0.0263(4) Uani 1 1 d . . . . .
N3 N 0.1553(3) -0.12824(7) 0.4888(3) 0.0353(5) Uani 1 1 d D . . . .
O1 O 0.1963(3) -0.10831(6) 0.8016(2) 0.0442(5) Uani 1 1 d . . . . .
O2 O 0.1524(3) -0.06360(6) 0.3305(2) 0.0409(5) Uani 1 1 d . . . . .
O3 O 0.2344(3) 0.05717(6) 0.1805(2) 0.0403(5) Uani 1 1 d D . . . .
O4 O 0.435(2) 0.1485(5) 0.8868(9) 0.046(2) Uani 0.53(4) 1 d . . P A 1
O5A O 0.418(2) 0.2316(3) 0.6950(19) 0.045(3) Uani 0.47(4) 1 d . . P A 2
O6 O 0.674(3) 0.1886(6) 0.768(3) 0.046(3) Uani 0.53(4) 1 d . . P A 1
O7 O 1.0716(3) 0.10955(6) 0.9254(2) 0.0386(4) Uani 1 1 d D . . . .
O8 O 0.8153(4) 0.21532(8) 1.2537(3) 0.0679(7) Uani 1 1 d D . . . .
O9 O 1.0994(3) 0.22758(7) 0.9805(3) 0.0497(5) Uani 1 1 d D . . . .
Na1 Na 0.86815(17) 0.16939(3) 1.03446(12) 0.0409(3) Uani 1 1 d . . . . .
S1 S 0.46635(9) 0.17952(2) 0.74974(7) 0.0314(2) Uani 1 1 d . . . . .
O4A O 0.367(3) 0.1651(8) 0.8706(18) 0.056(4) Uani 0.47(4) 1 d . . P A 2
O5 O 0.345(3) 0.2201(5) 0.7331(11) 0.053(4) Uani 0.53(4) 1 d . . P A 1
O6A O 0.678(4) 0.1747(7) 0.790(3) 0.047(3) Uani 0.47(4) 1 d . . P A 2
H1N H 0.225(5) 0.0007(12) 0.372(3) 0.070 Uiso 1 1 d D U . . .
H3A H 0.151(5) -0.1467(12) 0.403(3) 0.070 Uiso 1 1 d D U . . .
H3B H 0.167(5) -0.1398(13) 0.587(3) 0.070 Uiso 1 1 d D U . . .
H7A H 1.001(5) 0.0935(12) 0.842(3) 0.070 Uiso 1 1 d D U . . .
H7B H 1.175(4) 0.1235(12) 0.898(4) 0.070 Uiso 1 1 d D U . . .
H9A H 1.169(5) 0.2449(12) 1.058(3) 0.070 Uiso 1 1 d D U . . .
H9B H 1.182(5) 0.2197(13) 0.918(4) 0.070 Uiso 1 1 d D U . . .
H8A H 0.711(4) 0.2337(12) 1.220(5) 0.070 Uiso 1 1 d D U . . .
H8B H 0.910(4) 0.2352(11) 1.304(4) 0.070 Uiso 1 1 d D U . . .
H3O H 0.185(5) 0.0752(11) 0.094(3) 0.070 Uiso 1 1 d D 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
C1 C2 1.494(4) . ?
C2 O1 1.224(3) . ?
C2 C3 1.470(3) . ?
C3 N2 1.319(3) . ?
C3 C4 1.488(3) . ?
C4 O2 1.250(3) . ?
C4 N3 1.324(3) . ?
C5 C10 1.380(3) . ?
C5 C6 1.399(3) . ?
C5 N1 1.405(3) . ?
C6 O3 1.356(3) . ?
C6 C7 1.389(3) . ?
C7 C8 1.385(3) . ?
C8 C9 1.384(3) . ?
C9 C10 1.384(3) . ?
C9 S1 1.764(2) . ?
N1 N2 1.309(3) . ?
O1 Na1 2.299(2) 3_657 ?
O4 S1 1.504(8) . ?
O5A S1 1.537(10) . ?
O6 S1 1.44(2) . ?
O6 Na1 2.45(2) . ?
O7 Na1 2.475(2) . ?
O8 Na1 2.352(3) . ?
O9 Na1 2.382(2) . ?
Na1 O6A 2.24(2) . ?
S1 O5 1.397(5) . ?
S1 O4A 1.404(9) . ?
S1 O6A 1.44(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
O1 C2 C3 121.0(2) . . ?
O1 C2 C1 119.7(2) . . ?
C3 C2 C1 119.3(2) . . ?
N2 C3 C2 113.3(2) . . ?
N2 C3 C4 123.6(2) . . ?
C2 C3 C4 123.1(2) . . ?
O2 C4 N3 121.4(2) . . ?
O2 C4 C3 119.3(2) . . ?
N3 C4 C3 119.3(2) . . ?
C10 C5 C6 120.4(2) . . ?
C10 C5 N1 123.6(2) . . ?
C6 C5 N1 116.0(2) . . ?
O3 C6 C7 123.9(2) . . ?
O3 C6 C5 116.6(2) . . ?
C7 C6 C5 119.5(2) . . ?
C8 C7 C6 120.1(2) . . ?
C9 C8 C7 119.7(2) . . ?
C8 C9 C10 120.9(2) . . ?
C8 C9 S1 119.29(18) . . ?
C10 C9 S1 119.67(18) . . ?
C5 C10 C9 119.3(2) . . ?
N2 N1 C5 119.34(19) . . ?
N1 N2 C3 121.0(2) . . ?
C2 O1 Na1 152.47(18) . 3_657 ?
S1 O6 Na1 114.4(11) . . ?
O6A Na1 O8 123.4(6) . . ?
O1 Na1 O8 80.68(9) 3_657 . ?
O6A Na1 O9 93.9(7) . . ?
O1 Na1 O9 146.90(9) 3_657 . ?
O8 Na1 O9 90.05(9) . . ?
O1 Na1 O6 126.0(4) 3_657 . ?
O8 Na1 O6 118.3(5) . . ?
O9 Na1 O6 86.4(4) . . ?
O6A Na1 O7 88.1(6) . . ?
O1 Na1 O7 85.71(7) 3_657 . ?
O8 Na1 O7 148.53(10) . . ?
O9 Na1 O7 86.06(8) . . ?
O6 Na1 O7 92.6(5) . . ?
O5 S1 O6 116.0(7) . . ?
O4A S1 O6A 114.6(11) . . ?
O5 S1 O4 111.4(4) . . ?
O6 S1 O4 108.3(7) . . ?
O4A S1 O5A 112.6(5) . . ?
O6A S1 O5A 108.1(6) . . ?
O5 S1 C9 107.1(3) . . ?
O4A S1 C9 109.9(4) . . ?
O6 S1 C9 108.7(9) . . ?
O6A S1 C9 105.6(10) . . ?
O4 S1 C9 104.9(4) . . ?
O5A S1 C9 105.5(4) . . ?
S1 O6A Na1 127.6(17) . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_Compound3
_database_code_depnum_ccdc_archive 'CCDC 1857658'
_audit_update_record             
;
2019-01-03 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H28 Cu N6 O14 S2'
_chemical_formula_sum            'C20 H28 Cu N6 O14 S2'
_chemical_formula_weight         704.14

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.589(2)
_cell_length_b                   13.188(3)
_cell_length_c                   11.558(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.545(4)
_cell_angle_gamma                90
_cell_volume                     1385.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6240
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      34.81

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             726
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.020
_shelx_estimated_absorpt_T_min   0.698
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37290
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_av_R_equivalents  0.0800
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.414
_diffrn_reflns_theta_max         37.182
_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             7122
_reflns_number_gt                5063
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury CSD 3.10.3'
_computing_publication_material  
'SHELXL-2018/1 (Sheldrick, 2018), WinGX (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²+0.5826P] 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         7122
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
C1 C -0.03922(16) 0.36295(10) 0.95983(12) 0.0144(2) Uani 1 1 d . . . . .
C2 C -0.10451(18) 0.35607(12) 1.05150(14) 0.0198(3) Uani 1 1 d . . . . .
H2 H -0.194052 0.387867 1.041911 0.024 Uiso 1 1 calc R U . . .
C3 C -0.0355(2) 0.30158(13) 1.15728(14) 0.0233(3) Uani 1 1 d . . . . .
H3 H -0.079190 0.297292 1.218351 0.028 Uiso 1 1 calc R U . . .
C4 C 0.0979(2) 0.25356(12) 1.17254(14) 0.0230(3) Uani 1 1 d . . . . .
H4 H 0.143599 0.217517 1.243687 0.028 Uiso 1 1 calc R U . . .
C5 C 0.16314(18) 0.25951(12) 1.08101(14) 0.0201(3) Uani 1 1 d . . . . .
H5 H 0.252173 0.226887 1.090915 0.024 Uiso 1 1 calc R U . . .
C6 C 0.09565(16) 0.31417(10) 0.97443(12) 0.0148(2) Uani 1 1 d . . . . .
C7 C -0.49062(17) 0.53865(15) 0.85452(14) 0.0232(3) Uani 1 1 d . . . . .
H7A H -0.571828 0.582865 0.849630 0.035 Uiso 1 1 calc R U . . .
H7B H -0.407073 0.558568 0.921998 0.035 Uiso 1 1 calc R U . . .
H7C H -0.517188 0.470137 0.866227 0.035 Uiso 1 1 calc R U . . .
C8 C -0.45291(15) 0.54547(11) 0.73888(13) 0.0146(2) Uani 1 1 d . . . . .
C9 C -0.30510(14) 0.51280(10) 0.74023(12) 0.0130(2) Uani 1 1 d . . . . .
C10 C -0.24436(14) 0.53493(11) 0.63944(12) 0.0133(2) Uani 1 1 d . . . . .
N1 N -0.10692(13) 0.41864(9) 0.85257(11) 0.0146(2) Uani 1 1 d . . . . .
N2 N -0.23496(13) 0.46026(9) 0.83856(11) 0.0135(2) Uani 1 1 d . . . . .
N3 N -0.31387(15) 0.60251(11) 0.55534(13) 0.0206(3) Uani 1 1 d . . . . .
O1 O 0.07946(15) 0.28181(9) 0.74956(10) 0.0256(3) Uani 1 1 d . . . . .
O2 O 0.20144(12) 0.43312(9) 0.84722(10) 0.0201(2) Uani 1 1 d . . . . .
O3 O 0.31994(16) 0.27050(12) 0.90465(13) 0.0375(4) Uani 1 1 d . . . . .
O4 O -0.54384(12) 0.57569(9) 0.64322(10) 0.0197(2) Uani 1 1 d . . . . .
O5 O -0.12740(11) 0.49297(8) 0.63915(10) 0.0182(2) Uani 1 1 d . . . . .
O6 O 0.04338(12) 0.35289(8) 0.52703(10) 0.01539(19) Uani 1 1 d . . . . .
O7 O 0.17256(12) 0.53313(10) 0.63993(10) 0.0201(2) Uani 1 1 d . . . . .
S1 S 0.18223(4) 0.32433(3) 0.86040(3) 0.01604(7) Uani 1 1 d . . . . .
Cu1 Cu 0.000000 0.500000 0.500000 0.01175(6) Uani 1 2 d S . P . .
H1N H -0.069(2) 0.4264(15) 0.7996(19) 0.018 Uiso 1 1 d . U . . .
H3A H -0.399(2) 0.6216(15) 0.5547(18) 0.018 Uiso 1 1 d . U . . .
H3B H -0.275(2) 0.6205(15) 0.5040(18) 0.018 Uiso 1 1 d . U . . .
H6A H -0.017(2) 0.3212(17) 0.4868(19) 0.018 Uiso 1 1 d . U . . .
H6B H 0.052(2) 0.3316(15) 0.598(2) 0.018 Uiso 1 1 d . U . . .
H7D H 0.182(2) 0.5014(15) 0.703(2) 0.018 Uiso 1 1 d . U . . .
H7E H 0.249(2) 0.5520(16) 0.6366(18) 0.018 Uiso 1 1 d . 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
C1 C2 1.394(2) . ?
C1 C6 1.406(2) . ?
C1 N1 1.4092(18) . ?
C2 C3 1.391(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3960(19) . ?
C5 H5 0.9300 . ?
C6 S1 1.7721(16) . ?
C7 C8 1.494(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O4 1.2362(17) . ?
C8 C9 1.4767(19) . ?
C9 N2 1.3182(17) . ?
C9 C10 1.488(2) . ?
C10 O5 1.2516(17) . ?
C10 N3 1.3308(18) . ?
N1 N2 1.3071(17) . ?
N1 H1N 0.81(2) . ?
N3 H3A 0.85(2) . ?
N3 H3B 0.83(2) . ?
O1 S1 1.4573(12) . ?
O2 S1 1.4605(12) . ?
O3 S1 1.4422(13) . ?
O5 Cu1 2.3102(11) . ?
O6 Cu1 1.9879(12) . ?
O6 H6A 0.74(2) . ?
O6 H6B 0.85(2) . ?
O7 Cu1 1.9601(11) . ?
O7 H7D 0.82(2) . ?
O7 H7E 0.79(2) . ?

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 C1 C6 119.82(13) . . ?
C2 C1 N1 120.65(13) . . ?
C6 C1 N1 119.54(13) . . ?
C3 C2 C1 119.90(15) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.61(15) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.78(14) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.36(15) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.53(14) . . ?
C5 C6 S1 119.99(12) . . ?
C1 C6 S1 120.45(10) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 C9 120.33(13) . . ?
O4 C8 C7 121.12(13) . . ?
C9 C8 C7 118.53(12) . . ?
N2 C9 C8 112.78(12) . . ?
N2 C9 C10 123.97(12) . . ?
C8 C9 C10 123.23(12) . . ?
O5 C10 N3 122.35(14) . . ?
O5 C10 C9 119.32(12) . . ?
N3 C10 C9 118.26(12) . . ?
N2 N1 C1 118.66(12) . . ?
N2 N1 H1N 118.8(14) . . ?
C1 N1 H1N 122.5(14) . . ?
N1 N2 C9 121.95(12) . . ?
C10 N3 H3A 117.5(14) . . ?
C10 N3 H3B 118.5(14) . . ?
H3A N3 H3B 123.9(19) . . ?
C10 O5 Cu1 131.06(9) . . ?
Cu1 O6 H6A 111.6(16) . . ?
Cu1 O6 H6B 115.3(14) . . ?
H6A O6 H6B 104(2) . . ?
Cu1 O7 H7D 116.2(15) . . ?
Cu1 O7 H7E 125.8(15) . . ?
H7D O7 H7E 112(2) . . ?
O3 S1 O1 114.15(9) . . ?
O3 S1 O2 112.89(9) . . ?
O1 S1 O2 111.03(7) . . ?
O3 S1 C6 106.96(7) . . ?
O1 S1 C6 106.19(7) . . ?
O2 S1 C6 104.85(7) . . ?
O7 Cu1 O7 180.0 . 3_566 ?
O7 Cu1 O6 90.48(5) . . ?
O7 Cu1 O6 89.52(5) 3_566 . ?
O7 Cu1 O6 89.52(5) . 3_566 ?
O7 Cu1 O6 90.48(5) 3_566 3_566 ?
O6 Cu1 O6 180.0 . 3_566 ?
O7 Cu1 O5 94.07(5) . 3_566 ?
O7 Cu1 O5 85.93(5) 3_566 3_566 ?
O6 Cu1 O5 91.03(4) . 3_566 ?
O6 Cu1 O5 88.97(4) 3_566 3_566 ?
O7 Cu1 O5 85.93(5) . . ?
O7 Cu1 O5 94.07(5) 3_566 . ?
O6 Cu1 O5 88.97(4) . . ?
O6 Cu1 O5 91.03(4) 3_566 . ?
O5 Cu1 O5 180.00(6) 3_566 . ?

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
C6 C1 C2 C3 0.4(2) . . . . ?
N1 C1 C2 C3 -179.40(14) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C4 C5 C6 S1 178.17(12) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
N1 C1 C6 C5 179.62(13) . . . . ?
C2 C1 C6 S1 -178.63(12) . . . . ?
N1 C1 C6 S1 1.19(18) . . . . ?
O4 C8 C9 N2 -164.34(13) . . . . ?
C7 C8 C9 N2 14.16(19) . . . . ?
O4 C8 C9 C10 14.2(2) . . . . ?
C7 C8 C9 C10 -167.30(14) . . . . ?
N2 C9 C10 O5 8.3(2) . . . . ?
C8 C9 C10 O5 -170.12(13) . . . . ?
N2 C9 C10 N3 -168.87(14) . . . . ?
C8 C9 C10 N3 12.8(2) . . . . ?
C2 C1 N1 N2 -2.7(2) . . . . ?
C6 C1 N1 N2 177.43(13) . . . . ?
C1 N1 N2 C9 -179.53(13) . . . . ?
C8 C9 N2 N1 175.13(12) . . . . ?
C10 C9 N2 N1 -3.4(2) . . . . ?
N3 C10 O5 Cu1 -5.6(2) . . . . ?
C9 C10 O5 Cu1 177.40(9) . . . . ?
C5 C6 S1 O3 -1.02(15) . . . . ?
C1 C6 S1 O3 177.40(13) . . . . ?
C5 C6 S1 O1 121.26(13) . . . . ?
C1 C6 S1 O1 -60.32(13) . . . . ?
C5 C6 S1 O2 -121.12(12) . . . . ?
C1 C6 S1 O2 57.29(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O1 0.81(2) 2.55(2) 3.0367(19) 119.5(17) . yes
N1 H1N O2 0.81(2) 2.47(2) 2.9831(18) 121.7(17) . yes
N1 H1N O5 0.81(2) 1.97(2) 2.6030(17) 134.9(19) . yes
N3 H3A O4 0.85(2) 2.06(2) 2.7284(19) 134.7(18) . yes
N3 H3B O6 0.83(2) 2.38(2) 3.0903(19) 143.5(18) 3_566 yes
O6 H6A O3 0.74(2) 1.97(2) 2.7040(16) 171(2) 4_565 yes
O6 H6B O1 0.85(2) 1.81(2) 2.6548(17) 177(2) . yes
O6 H6B S1 0.85(2) 2.89(2) 3.6738(14) 154.8(17) . yes
O7 H7D O2 0.82(2) 1.85(2) 2.6710(17) 179(2) . yes
O7 H7D S1 0.82(2) 2.96(2) 3.7328(14) 158.0(18) . yes
O7 H7E O4 0.79(2) 1.98(2) 2.7652(17) 170(2) 1_655 yes

_refine_diff_density_max         0.605
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_compound7
_database_code_depnum_ccdc_archive 'CCDC 1857659'
_audit_update_record             
;
2019-01-03 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H58 Cu N8 O18 S2'
_chemical_formula_sum            'C46 H58 Cu N8 O18 S2'
_chemical_formula_weight         1138.66

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.4839(11)
_cell_length_b                   11.1918(15)
_cell_length_c                   16.739(3)
_cell_angle_alpha                106.232(10)
_cell_angle_beta                 102.070(10)
_cell_angle_gamma                97.821(10)
_cell_volume                     1287.8(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2383
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      20.03

_exptl_crystal_description       Plates
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_F_000             595
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.586
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   
'The quality of the data is poor since the crystal is thin and very weakly diffracting, therefore justifying the A-alert in the CIF report. Attempts to obtain better crystals failed. Collect data at lower temperature also failed because the thin plates cracked.'
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26077
_diffrn_reflns_av_unetI/netI     0.2055
_diffrn_reflns_av_R_equivalents  0.3122
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.625
_diffrn_reflns_theta_max         25.286
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4621
_reflns_number_gt                1878
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury CSD 3.10.3'
_computing_publication_material  
'SHELXL-2018/3 (Sheldrick, 2018), WinGX (Farrugia, 2012)'
_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)+(0.1301P)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         4621
_refine_ls_number_parameters     367
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.2432
_refine_ls_R_factor_gt           0.0916
_refine_ls_wR_factor_ref         0.2710
_refine_ls_wR_factor_gt          0.1987
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.002
_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 0.9986(13) 0.7195(9) 0.7651(6) 0.066(3) Uani 1 1 d . . . . .
H1A H 1.059773 0.789910 0.816157 0.100 Uiso 1 1 calc R U . . .
H1B H 0.899841 0.743836 0.730431 0.100 Uiso 1 1 calc R U . . .
H1C H 1.087324 0.695520 0.732885 0.100 Uiso 1 1 calc R U . . .
C2 C 0.9194(12) 0.6098(9) 0.7899(7) 0.056(2) Uani 1 1 d . . . . .
C3 C 0.8109(11) 0.4930(8) 0.7209(5) 0.047(2) Uani 1 1 d . . . . .
C4 C 0.7222(12) 0.3756(9) 0.7346(6) 0.053(2) Uani 1 1 d . . . . .
C5 C 0.6723(13) 0.2875(9) 0.8518(6) 0.054(2) Uani 1 1 d . . . . .
C6 C 0.5596(14) 0.1717(10) 0.8017(6) 0.064(3) Uani 1 1 d . . . . .
H6 H 0.522146 0.153041 0.742200 0.076 Uiso 1 1 calc R U . . .
C7 C 0.5018(15) 0.0832(10) 0.8387(7) 0.076(3) Uani 1 1 d . . . . .
H7 H 0.421659 0.006447 0.804807 0.091 Uiso 1 1 calc R U . . .
C8 C 0.5638(17) 0.1096(12) 0.9263(8) 0.082(3) Uani 1 1 d . . . . .
H8 H 0.528991 0.048675 0.951337 0.098 Uiso 1 1 calc R U . . .
C9 C 0.6751(16) 0.2231(12) 0.9768(7) 0.077(3) Uani 1 1 d . . . . .
H9 H 0.711979 0.240346 1.036178 0.093 Uiso 1 1 calc R U . . .
C10 C 0.7346(13) 0.3143(10) 0.9406(6) 0.063(3) Uani 1 1 d . . . . .
H10 H 0.814139 0.391086 0.974890 0.076 Uiso 1 1 calc R U . . .
C11 C 0.6934(11) 0.4311(8) 0.4915(5) 0.044(2) Uani 1 1 d . . . . .
C12 C 0.6068(11) 0.3386(7) 0.4145(5) 0.040(2) Uani 1 1 d . . . . .
C13 C 0.5965(11) 0.3673(8) 0.3356(5) 0.045(2) Uani 1 1 d . . . . .
C14 C 0.5073(11) 0.2795(9) 0.2529(6) 0.053(2) Uani 1 1 d . . . . .
H14 H 0.449605 0.198155 0.248653 0.064 Uiso 1 1 calc R U . . .
C15 C 0.5027(12) 0.3099(10) 0.1789(6) 0.059(3) Uani 1 1 d . . . . .
H15 H 0.439942 0.250598 0.125668 0.071 Uiso 1 1 calc R U . . .
C16 C 0.5907(14) 0.4279(11) 0.1836(6) 0.064(3) Uani 1 1 d . . . . .
H16 H 0.590322 0.447547 0.133162 0.077 Uiso 1 1 calc R U . . .
C17 C 0.6789(14) 0.5170(10) 0.2610(7) 0.065(3) Uani 1 1 d . . . . .
H17 H 0.736404 0.597120 0.262756 0.077 Uiso 1 1 calc R U . . .
C18 C 0.6843(12) 0.4894(8) 0.3383(6) 0.050(2) Uani 1 1 d . . . . .
C19 C 0.7773(12) 0.5789(9) 0.4183(6) 0.055(2) Uani 1 1 d . . . . .
H19 H 0.840628 0.658007 0.420972 0.066 Uiso 1 1 calc R U . . .
C20 C 0.7760(12) 0.5512(9) 0.4929(6) 0.055(2) Uani 1 1 d . . . . .
H20 H 0.831416 0.613929 0.545645 0.066 Uiso 1 1 calc R U . . .
C21 C 1.0561(19) 0.0893(13) 0.9229(9) 0.121(5) Uani 1 1 d . . . . .
H21A H 0.967439 0.013350 0.886488 0.181 Uiso 1 1 calc R U . . .
H21B H 1.008504 0.130842 0.969916 0.181 Uiso 1 1 calc R U . . .
H21C H 1.171956 0.067482 0.944978 0.181 Uiso 1 1 calc R U . . .
C22 C 1.1953(15) 0.3021(12) 0.9200(7) 0.092(4) Uani 1 1 d . . . . .
H22A H 1.326107 0.300804 0.931928 0.138 Uiso 1 1 calc R U . . .
H22B H 1.162343 0.334630 0.973228 0.138 Uiso 1 1 calc R U . . .
H22C H 1.168792 0.355595 0.885023 0.138 Uiso 1 1 calc R U . . .
C23 C 1.0168(15) 0.1399(12) 0.7902(9) 0.085(4) Uani 1 1 d . . . . .
H23 H 0.942821 0.058720 0.763076 0.102 Uiso 1 1 calc R U . . .
N1 N 0.7399(11) 0.3814(8) 0.8187(5) 0.056(2) Uani 1 1 d . . . . .
N2 N 0.7965(9) 0.5039(7) 0.6431(5) 0.0476(18) Uani 1 1 d . . . . .
N3 N 0.7046(10) 0.4124(7) 0.5730(5) 0.0466(19) Uani 1 1 d . . . . .
N4 N 1.0866(12) 0.1727(9) 0.8741(7) 0.077(3) Uani 1 1 d . . . . .
O1 O 0.9438(9) 0.6154(7) 0.8661(4) 0.075(2) Uani 1 1 d . . . . .
O2 O 0.6379(9) 0.2805(6) 0.6732(4) 0.0618(17) Uani 1 1 d . . . . .
O3 O 0.6172(7) 0.1009(5) 0.3608(3) 0.0523(15) Uani 1 1 d . . . . .
O4 O 0.5231(7) 0.1719(5) 0.4923(3) 0.0481(15) Uani 1 1 d . . . . .
O5 O 0.3109(7) 0.1518(6) 0.3570(4) 0.0581(17) Uani 1 1 d . . . . .
O6 O 1.0054(10) 0.1242(8) 0.4179(5) 0.084(2) Uani 1 1 d . . . . .
O7 O 0.8906(10) 0.1226(7) 0.5766(4) 0.071(2) Uani 1 1 d . . . . .
O8 O 1.2545(8) 0.0899(6) 0.5735(4) 0.0586(17) Uani 1 1 d D . . . .
O9 O 1.0400(11) 0.2064(8) 0.7438(5) 0.095(3) Uani 1 1 d . . . . .
S1 S 0.5054(3) 0.1788(2) 0.40548(14) 0.0436(6) Uani 1 1 d . . . . .
Cu1 Cu 1.000000 0.000000 0.500000 0.0493(6) Uani 1 2 d S . P . .
H6A H 0.885(11) 0.136(8) 0.396(5) 0.074 Uiso 1 1 d D U . . .
H6C H 1.096(10) 0.141(9) 0.396(6) 0.074 Uiso 1 1 d D U . . .
H7A H 0.770(11) 0.144(8) 0.567(5) 0.074 Uiso 1 1 d D U . . .
H7B H 0.955(10) 0.155(8) 0.636(5) 0.074 Uiso 1 1 d D U . . .
H8B H 1.331(9) 0.069(8) 0.535(4) 0.074 Uiso 1 1 d D U . . .
H8C H 1.297(10) 0.088(8) 0.630(2) 0.074 Uiso 1 1 d D U . . .
H1N H 0.824(13) 0.456(9) 0.848(6) 0.074 Uiso 1 1 d . U . . .
H3N H 0.680(13) 0.342(9) 0.584(6) 0.074 Uiso 1 1 d . 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
C1 C2 1.490(12) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.233(10) . ?
C2 C3 1.475(12) . ?
C3 N2 1.326(10) . ?
C3 C4 1.489(12) . ?
C4 O2 1.233(10) . ?
C4 N1 1.367(11) . ?
C5 C6 1.376(12) . ?
C5 C10 1.393(11) . ?
C5 N1 1.402(11) . ?
C6 C7 1.374(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.375(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.356(14) . ?
C8 H8 0.9300 . ?
C9 C10 1.393(13) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.369(10) . ?
C11 C20 1.393(11) . ?
C11 N3 1.424(10) . ?
C12 C13 1.434(10) . ?
C12 S1 1.797(8) . ?
C13 C14 1.415(11) . ?
C13 C18 1.418(11) . ?
C14 C15 1.368(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.366(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.359(12) . ?
C16 H16 0.9300 . ?
C17 C18 1.406(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.398(11) . ?
C19 C20 1.370(11) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 N4 1.426(13) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 N4 1.465(13) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 O9 1.237(13) . ?
C23 N4 1.317(13) . ?
C23 H23 0.9300 . ?
N1 H1N 0.92(9) . ?
N2 N3 1.303(9) . ?
N3 H3N 0.87(9) . ?
O3 S1 1.454(6) . ?
O4 S1 1.456(5) . ?
O5 S1 1.455(5) . ?
O6 Cu1 2.214(7) . ?
O6 H6A 0.94(8) . ?
O6 H6C 0.85(8) . ?
O7 Cu1 1.989(6) . ?
O7 H7A 0.96(8) . ?
O7 H7B 0.95(8) . ?
O8 Cu1 1.990(6) . ?
O8 H8B 0.95(2) . ?
O8 H8C 0.94(2) . ?

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 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 120.2(9) . . ?
O1 C2 C1 121.2(9) . . ?
C3 C2 C1 118.5(8) . . ?
N2 C3 C2 112.3(8) . . ?
N2 C3 C4 122.4(8) . . ?
C2 C3 C4 125.3(8) . . ?
O2 C4 N1 123.2(9) . . ?
O2 C4 C3 121.2(8) . . ?
N1 C4 C3 115.6(8) . . ?
C6 C5 C10 120.0(9) . . ?
C6 C5 N1 124.0(8) . . ?
C10 C5 N1 115.9(9) . . ?
C7 C6 C5 120.7(9) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.2(10) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 120.9(10) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.7(10) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 118.4(10) . . ?
C9 C10 H10 120.8 . . ?
C5 C10 H10 120.8 . . ?
C12 C11 C20 120.1(8) . . ?
C12 C11 N3 123.5(8) . . ?
C20 C11 N3 116.4(8) . . ?
C11 C12 C13 119.6(7) . . ?
C11 C12 S1 123.6(6) . . ?
C13 C12 S1 116.8(6) . . ?
C14 C13 C18 116.4(8) . . ?
C14 C13 C12 124.2(8) . . ?
C18 C13 C12 119.4(8) . . ?
C15 C14 C13 122.4(9) . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C16 C15 C14 119.7(9) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 121.0(9) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 120.8(9) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 121.6(9) . . ?
C19 C18 C13 118.7(8) . . ?
C17 C18 C13 119.6(9) . . ?
C20 C19 C18 120.6(9) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C11 121.4(8) . . ?
C19 C20 H20 119.3 . . ?
C11 C20 H20 119.3 . . ?
N4 C21 H21A 109.5 . . ?
N4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O9 C23 N4 126.4(12) . . ?
O9 C23 H23 116.8 . . ?
N4 C23 H23 116.8 . . ?
C4 N1 C5 128.9(9) . . ?
C4 N1 H1N 103(6) . . ?
C5 N1 H1N 128(6) . . ?
N3 N2 C3 122.5(7) . . ?
N2 N3 C11 119.5(7) . . ?
N2 N3 H3N 110(6) . . ?
C11 N3 H3N 129(6) . . ?
C23 N4 C21 123.0(12) . . ?
C23 N4 C22 118.6(10) . . ?
C21 N4 C22 118.4(10) . . ?
Cu1 O6 H6A 111(5) . . ?
Cu1 O6 H6C 124(6) . . ?
H6A O6 H6C 123(7) . . ?
Cu1 O7 H7A 131(5) . . ?
Cu1 O7 H7B 117(5) . . ?
H7A O7 H7B 111(6) . . ?
Cu1 O8 H8B 103(5) . . ?
Cu1 O8 H8C 122(5) . . ?
H8B O8 H8C 118(5) . . ?
O3 S1 O5 113.2(3) . . ?
O3 S1 O4 111.6(3) . . ?
O5 S1 O4 111.8(3) . . ?
O3 S1 C12 104.4(3) . . ?
O5 S1 C12 107.6(4) . . ?
O4 S1 C12 107.8(4) . . ?
O7 Cu1 O7 180.0 . 2_756 ?
O7 Cu1 O8 90.3(3) . 2_756 ?
O7 Cu1 O8 89.7(3) 2_756 2_756 ?
O7 Cu1 O8 89.7(3) . . ?
O7 Cu1 O8 90.3(3) 2_756 . ?
O8 Cu1 O8 180.0 2_756 . ?
O7 Cu1 O6 89.4(3) . . ?
O7 Cu1 O6 90.6(3) 2_756 . ?
O8 Cu1 O6 88.3(3) 2_756 . ?
O8 Cu1 O6 91.7(3) . . ?
O7 Cu1 O6 90.6(3) . 2_756 ?
O7 Cu1 O6 89.4(3) 2_756 2_756 ?
O8 Cu1 O6 91.7(3) 2_756 2_756 ?
O8 Cu1 O6 88.3(3) . 2_756 ?
O6 Cu1 O6 180.0 . 2_756 ?

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
O1 C2 C3 N2 179.3(8) . . . . ?
C1 C2 C3 N2 -1.0(11) . . . . ?
O1 C2 C3 C4 0.4(14) . . . . ?
C1 C2 C3 C4 -179.8(8) . . . . ?
N2 C3 C4 O2 3.3(13) . . . . ?
C2 C3 C4 O2 -178.0(8) . . . . ?
N2 C3 C4 N1 -176.2(7) . . . . ?
C2 C3 C4 N1 2.5(13) . . . . ?
C10 C5 C6 C7 2.4(15) . . . . ?
N1 C5 C6 C7 178.7(9) . . . . ?
C5 C6 C7 C8 -2.6(16) . . . . ?
C6 C7 C8 C9 2.5(17) . . . . ?
C7 C8 C9 C10 -2.3(18) . . . . ?
C8 C9 C10 C5 2.1(15) . . . . ?
C6 C5 C10 C9 -2.1(14) . . . . ?
N1 C5 C10 C9 -178.7(8) . . . . ?
C20 C11 C12 C13 -2.0(12) . . . . ?
N3 C11 C12 C13 177.8(7) . . . . ?
C20 C11 C12 S1 177.1(6) . . . . ?
N3 C11 C12 S1 -3.1(12) . . . . ?
C11 C12 C13 C14 -178.7(8) . . . . ?
S1 C12 C13 C14 2.1(10) . . . . ?
C11 C12 C13 C18 3.1(11) . . . . ?
S1 C12 C13 C18 -176.1(6) . . . . ?
C18 C13 C14 C15 -0.8(12) . . . . ?
C12 C13 C14 C15 -179.0(8) . . . . ?
C13 C14 C15 C16 1.7(13) . . . . ?
C14 C15 C16 C17 -1.8(14) . . . . ?
C15 C16 C17 C18 1.0(15) . . . . ?
C16 C17 C18 C19 178.8(9) . . . . ?
C16 C17 C18 C13 -0.1(13) . . . . ?
C14 C13 C18 C19 -178.9(8) . . . . ?
C12 C13 C18 C19 -0.6(12) . . . . ?
C14 C13 C18 C17 0.0(12) . . . . ?
C12 C13 C18 C17 178.3(7) . . . . ?
C17 C18 C19 C20 178.1(8) . . . . ?
C13 C18 C19 C20 -3.1(13) . . . . ?
C18 C19 C20 C11 4.3(14) . . . . ?
C12 C11 C20 C19 -1.7(13) . . . . ?
N3 C11 C20 C19 178.5(8) . . . . ?
O2 C4 N1 C5 0.4(15) . . . . ?
C3 C4 N1 C5 179.9(8) . . . . ?
C6 C5 N1 C4 -5.3(15) . . . . ?
C10 C5 N1 C4 171.1(8) . . . . ?
C2 C3 N2 N3 -179.2(7) . . . . ?
C4 C3 N2 N3 -0.3(12) . . . . ?
C3 N2 N3 C11 179.4(7) . . . . ?
C12 C11 N3 N2 177.1(7) . . . . ?
C20 C11 N3 N2 -3.1(11) . . . . ?
O9 C23 N4 C21 -178.7(11) . . . . ?
O9 C23 N4 C22 3.3(17) . . . . ?
C11 C12 S1 O3 -115.3(7) . . . . ?
C13 C12 S1 O3 63.8(6) . . . . ?
C11 C12 S1 O5 124.3(7) . . . . ?
C13 C12 S1 O5 -56.6(7) . . . . ?
C11 C12 S1 O4 3.5(8) . . . . ?
C13 C12 S1 O4 -177.4(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1B O5 0.96 2.55 3.492(10) 168.2 2_666 yes
C6 H6 O2 0.93 2.26 2.872(11) 122.5 . yes
O6 H6A O3 0.94(8) 1.92(8) 2.813(8) 159(8) . yes
O6 H6A S1 0.94(8) 2.97(8) 3.845(7) 155(7) . yes
O6 H6C O5 0.85(8) 1.86(8) 2.705(9) 168(9) 1_655 yes
O6 H6C S1 0.85(8) 3.00(8) 3.767(7) 150(7) 1_655 yes
O7 H7A O2 0.96(8) 2.47(9) 3.148(9) 127(6) . yes
O7 H7A O4 0.96(8) 2.12(8) 3.014(8) 156(7) . yes
O7 H7B O9 0.95(8) 1.68(8) 2.628(10) 172(8) . yes
O8 H8B O4 0.95(2) 2.08(6) 2.840(8) 135(7) 1_655 yes
O8 H8C O3 0.94(2) 2.32(8) 2.851(8) 115(6) 2_756 yes
N1 H1N O1 0.92(9) 1.79(9) 2.657(10) 156(8) . yes
N3 H3N O2 0.87(9) 1.87(9) 2.603(9) 141(8) . yes
N3 H3N O4 0.87(9) 2.09(9) 2.669(9) 123(7) . yes
C1 H1B O5 0.96 2.55 3.492(10) 168.2 2_666 yes
C6 H6 O2 0.93 2.26 2.872(11) 122.5 . yes
O6 H6A O3 0.94(8) 1.92(8) 2.813(8) 159(8) . yes
O6 H6A S1 0.94(8) 2.97(8) 3.845(7) 155(7) . yes
O6 H6C O5 0.85(8) 1.86(8) 2.705(9) 168(9) 1_655 yes
O6 H6C S1 0.85(8) 3.00(8) 3.767(7) 150(7) 1_655 yes
O7 H7A O2 0.96(8) 2.47(9) 3.148(9) 127(6) . yes
O7 H7A O4 0.96(8) 2.12(8) 3.014(8) 156(7) . yes
O7 H7B O9 0.95(8) 1.68(8) 2.628(10) 172(8) . yes
O8 H8B O4 0.95(2) 2.08(6) 2.840(8) 135(7) 1_655 yes
O8 H8C O3 0.94(2) 2.32(8) 2.851(8) 115(6) 2_756 yes
N1 H1N O1 0.92(9) 1.79(9) 2.657(10) 156(8) . yes
N3 H3N O2 0.87(9) 1.87(9) 2.603(9) 141(8) . yes
N3 H3N O4 0.87(9) 2.09(9) 2.669(9) 123(7) . yes

_refine_diff_density_max         0.624
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.096

####################################################################### 
# 
# 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_Compound2
_database_code_depnum_ccdc_archive 'CCDC 1857660'
_audit_update_record             
;
2019-01-03 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H17 Cu N3 O9 S'
_chemical_formula_sum            'C10 H17 Cu N3 O9 S'
_chemical_formula_weight         418.86

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   21.9238(18)
_cell_length_b                   6.6867(5)
_cell_length_c                   22.2697(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3264.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8261
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      24.91

_exptl_crystal_description       Plates
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_F_000             1720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.517
_shelx_estimated_absorpt_T_min   0.839
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41628
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.607
_diffrn_reflns_theta_max         25.438
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3003
_reflns_number_gt                2142
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury CSD 3.10.3'
_computing_publication_material  
'SHELXL-2018/1 (Sheldrick, 2018), WinGX (Farrugia, 2012)'
_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)+(0.0616P)²+4.6996P] 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         3003
_refine_ls_number_parameters     248
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.087
_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 0.67698(2) 0.10254(7) 0.59632(2) 0.03350(18) Uani 1 1 d . . . . .
S2 S 0.56211(5) -0.13488(16) 0.58465(5) 0.0383(3) Uani 1 1 d . . . . .
O3 O 0.58690(14) -0.2859(5) 0.62474(15) 0.0518(8) Uani 1 1 d . . . . .
O4 O 0.51615(13) -0.2099(5) 0.54356(14) 0.0517(8) Uani 1 1 d . . . . .
O1 O 0.77367(14) 0.2118(5) 0.82181(13) 0.0528(8) Uani 1 1 d . . . . .
N2 N 0.65039(15) 0.1740(5) 0.72334(14) 0.0314(7) Uani 1 1 d . . . . .
O7 O 0.65492(14) 0.4135(4) 0.55737(14) 0.0437(7) Uani 1 1 d D . . . .
O2 O 0.75050(13) 0.1724(5) 0.63754(12) 0.0417(7) Uani 1 1 d . . . . .
C6 C 0.52849(18) 0.0499(6) 0.62954(17) 0.0324(9) Uani 1 1 d . . . . .
O5 O 0.61086(13) -0.0304(5) 0.55155(13) 0.0499(8) Uani 1 1 d . . . . .
C3 C 0.70966(17) 0.1800(6) 0.73705(17) 0.0306(8) Uani 1 1 d . . . . .
N3 N 0.62925(14) 0.1434(5) 0.66988(14) 0.0298(7) Uani 1 1 d . . . . .
O6 O 0.72780(14) 0.0417(5) 0.52669(14) 0.0510(8) Uani 1 1 d D . . . .
N1 N 0.81694(16) 0.1887(6) 0.71258(18) 0.0392(8) Uani 1 1 d . . . . .
O8 O 0.57834(16) 0.5031(7) 0.46326(17) 0.0658(10) Uani 1 1 d D . . . .
C4 C 0.76013(18) 0.1783(6) 0.69337(18) 0.0325(9) Uani 1 1 d . . . . .
C5 C 0.56429(18) 0.1659(6) 0.66802(17) 0.0315(8) Uani 1 1 d . . . . .
C2 C 0.72106(19) 0.2038(6) 0.80145(18) 0.0367(9) Uani 1 1 d . . . . .
C7 C 0.46563(19) 0.0759(7) 0.6275(2) 0.0410(10) Uani 1 1 d . . . . .
H6 H 0.442098 -0.000249 0.601309 0.049 Uiso 1 1 calc R U . . .
C10 C 0.5355(2) 0.3074(7) 0.70407(19) 0.0415(10) Uani 1 1 d . . . . .
H9 H 0.558629 0.388071 0.729310 0.050 Uiso 1 1 calc R U . . .
C1 C 0.6686(2) 0.2151(8) 0.84375(19) 0.0523(12) Uani 1 1 d . . . . .
H4 H 0.651660 0.083965 0.849259 0.078 Uiso 1 1 calc R U . . .
H5 H 0.637986 0.302435 0.827552 0.078 Uiso 1 1 calc R U . . .
H3 H 0.682308 0.266143 0.881708 0.078 Uiso 1 1 calc R U . . .
C9 C 0.4732(2) 0.3289(8) 0.7027(2) 0.0496(12) Uani 1 1 d . . . . .
H8 H 0.454344 0.421057 0.727953 0.060 Uiso 1 1 calc R U . . .
C8 C 0.4384(2) 0.2149(8) 0.6643(2) 0.0506(12) Uani 1 1 d . . . . .
H7 H 0.396319 0.231915 0.663161 0.061 Uiso 1 1 calc R U . . .
O9 O 0.6831(2) 0.8038(9) 0.43953(17) 0.0886(15) Uani 1 1 d D . . . .
H1 H 0.845(4) 0.191(13) 0.687(4) 0.133 Uiso 1 1 d . U . . .
H2 H 0.823(3) 0.209(13) 0.753(4) 0.133 Uiso 1 1 d . U . . .
H10 H 0.633(3) 0.418(11) 0.5209(17) 0.133 Uiso 1 1 d D U . . .
H11 H 0.633(3) 0.489(10) 0.587(2) 0.133 Uiso 1 1 d D U . . .
H13 H 0.7670(17) -0.002(11) 0.538(3) 0.133 Uiso 1 1 d D U . . .
H12 H 0.711(3) -0.045(9) 0.497(3) 0.133 Uiso 1 1 d D U . . .
H14 H 0.564(3) 0.381(6) 0.448(3) 0.133 Uiso 1 1 d D U . . .
H15 H 0.548(2) 0.593(8) 0.475(3) 0.133 Uiso 1 1 d D U . . .
H17 H 0.703(3) 0.783(12) 0.400(3) 0.133 Uiso 1 1 d D U . . .
H16 H 0.654(3) 0.703(9) 0.448(3) 0.133 Uiso 1 1 d D 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 O2 1.913(3) . ?
Cu1 O6 1.952(3) . ?
Cu1 N3 1.963(3) . ?
Cu1 O5 1.971(3) . ?
Cu1 O7 2.305(3) . ?
S2 O4 1.451(3) . ?
S2 O3 1.453(3) . ?
S2 O5 1.474(3) . ?
S2 C6 1.752(4) . ?
O1 C2 1.240(5) . ?
N2 N3 1.294(4) . ?
N2 C3 1.335(5) . ?
O7 H10 0.95(2) . ?
O7 H11 0.95(2) . ?
O2 C4 1.262(5) . ?
C6 C7 1.390(6) . ?
C6 C5 1.397(6) . ?
C3 C2 1.464(6) . ?
C3 C4 1.473(5) . ?
N3 C5 1.433(5) . ?
O6 H13 0.94(2) . ?
O6 H12 0.95(2) . ?
N1 C4 1.319(5) . ?
N1 H1 0.84(8) . ?
N1 H2 0.93(9) . ?
O8 H14 0.94(2) . ?
O8 H15 0.93(2) . ?
C5 C10 1.392(6) . ?
C2 C1 1.489(6) . ?
C7 C8 1.375(6) . ?
C7 H6 0.9300 . ?
C10 C9 1.374(6) . ?
C10 H9 0.9300 . ?
C1 H4 0.9600 . ?
C1 H5 0.9600 . ?
C1 H3 0.9600 . ?
C9 C8 1.377(7) . ?
C9 H8 0.9300 . ?
C8 H7 0.9300 . ?
O9 H17 1.00(6) . ?
O9 H16 0.94(2) . ?

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
O2 Cu1 O6 87.20(12) . . ?
O2 Cu1 N3 90.84(12) . . ?
O6 Cu1 N3 174.92(14) . . ?
O2 Cu1 O5 166.53(14) . . ?
O6 Cu1 O5 85.64(13) . . ?
N3 Cu1 O5 95.32(13) . . ?
O2 Cu1 O7 97.88(12) . . ?
O6 Cu1 O7 90.51(13) . . ?
N3 Cu1 O7 94.40(12) . . ?
O5 Cu1 O7 93.58(13) . . ?
O4 S2 O3 114.0(2) . . ?
O4 S2 O5 110.61(19) . . ?
O3 S2 O5 111.42(19) . . ?
O4 S2 C6 108.15(19) . . ?
O3 S2 C6 107.27(19) . . ?
O5 S2 C6 104.84(19) . . ?
N3 N2 C3 124.3(3) . . ?
Cu1 O7 H10 117(4) . . ?
Cu1 O7 H11 109(5) . . ?
H10 O7 H11 109(4) . . ?
C4 O2 Cu1 128.4(3) . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 S2 119.1(3) . . ?
C5 C6 S2 120.3(3) . . ?
S2 O5 Cu1 119.60(18) . . ?
N2 C3 C2 113.2(3) . . ?
N2 C3 C4 125.4(3) . . ?
C2 C3 C4 121.3(3) . . ?
N2 N3 C5 111.5(3) . . ?
N2 N3 Cu1 126.8(3) . . ?
C5 N3 Cu1 121.4(2) . . ?
Cu1 O6 H13 111(4) . . ?
Cu1 O6 H12 117(5) . . ?
H13 O6 H12 111(4) . . ?
C4 N1 H1 119(6) . . ?
C4 N1 H2 118(5) . . ?
H1 N1 H2 123(7) . . ?
H14 O8 H15 116(4) . . ?
O2 C4 N1 118.6(4) . . ?
O2 C4 C3 121.7(3) . . ?
N1 C4 C3 119.7(4) . . ?
C10 C5 C6 118.4(4) . . ?
C10 C5 N3 120.4(4) . . ?
C6 C5 N3 121.2(3) . . ?
O1 C2 C3 121.4(4) . . ?
O1 C2 C1 119.0(4) . . ?
C3 C2 C1 119.6(4) . . ?
C8 C7 C6 119.7(4) . . ?
C8 C7 H6 120.2 . . ?
C6 C7 H6 120.2 . . ?
C9 C10 C5 120.7(4) . . ?
C9 C10 H9 119.7 . . ?
C5 C10 H9 119.7 . . ?
C2 C1 H4 109.5 . . ?
C2 C1 H5 109.5 . . ?
H4 C1 H5 109.5 . . ?
C2 C1 H3 109.5 . . ?
H4 C1 H3 109.5 . . ?
H5 C1 H3 109.5 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H8 119.8 . . ?
C8 C9 H8 119.8 . . ?
C7 C8 C9 120.3(4) . . ?
C7 C8 H7 119.8 . . ?
C9 C8 H7 119.8 . . ?
H17 O9 H16 111(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
O4 S2 C6 C7 9.8(4) . . . . ?
O3 S2 C6 C7 -113.6(4) . . . . ?
O5 S2 C6 C7 127.9(4) . . . . ?
O4 S2 C6 C5 -171.8(3) . . . . ?
O3 S2 C6 C5 64.8(4) . . . . ?
O5 S2 C6 C5 -53.8(4) . . . . ?
O4 S2 O5 Cu1 176.08(19) . . . . ?
O3 S2 O5 Cu1 -56.0(3) . . . . ?
C6 S2 O5 Cu1 59.7(3) . . . . ?
N3 N2 C3 C2 -176.2(3) . . . . ?
N3 N2 C3 C4 8.1(6) . . . . ?
C3 N2 N3 C5 -173.9(3) . . . . ?
C3 N2 N3 Cu1 -0.9(5) . . . . ?
Cu1 O2 C4 N1 165.8(3) . . . . ?
Cu1 O2 C4 C3 -16.1(5) . . . . ?
N2 C3 C4 O2 0.6(6) . . . . ?
C2 C3 C4 O2 -174.8(4) . . . . ?
N2 C3 C4 N1 178.7(4) . . . . ?
C2 C3 C4 N1 3.3(6) . . . . ?
C7 C6 C5 C10 0.0(6) . . . . ?
S2 C6 C5 C10 -178.3(3) . . . . ?
C7 C6 C5 N3 -178.9(4) . . . . ?
S2 C6 C5 N3 2.8(5) . . . . ?
N2 N3 C5 C10 34.6(5) . . . . ?
Cu1 N3 C5 C10 -138.8(3) . . . . ?
N2 N3 C5 C6 -146.5(4) . . . . ?
Cu1 N3 C5 C6 40.1(5) . . . . ?
N2 C3 C2 O1 179.9(4) . . . . ?
C4 C3 C2 O1 -4.2(6) . . . . ?
N2 C3 C2 C1 1.0(5) . . . . ?
C4 C3 C2 C1 176.9(4) . . . . ?
C5 C6 C7 C8 -1.0(6) . . . . ?
S2 C6 C7 C8 177.4(3) . . . . ?
C6 C5 C10 C9 1.5(6) . . . . ?
N3 C5 C10 C9 -179.6(4) . . . . ?
C5 C10 C9 C8 -2.0(7) . . . . ?
C6 C7 C8 C9 0.5(7) . . . . ?
C10 C9 C8 C7 1.0(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.84(8) 2.05(8) 2.881(5) 177(9) 7_765 yes
N1 H2 O1 0.93(9) 1.87(8) 2.616(5) 135(6) . yes
O7 H10 O8 0.95(2) 1.84(3) 2.751(5) 160(6) . yes
O7 H11 S2 0.95(2) 2.96(6) 3.691(3) 135(5) 1_565 yes
O7 H11 O3 0.95(2) 2.00(3) 2.918(4) 160(7) 1_565 yes
O6 H13 O7 0.94(2) 1.85(2) 2.795(5) 177(7) 7_755 yes
O6 H12 O9 0.95(2) 1.74(2) 2.694(5) 177(7) 1_545 yes
O8 H14 O4 0.94(2) 2.11(5) 2.856(5) 135(6) 5_656 yes
O8 H15 O4 0.93(2) 2.13(4) 2.956(5) 147(7) 1_565 yes
O9 H17 O1 1.00(6) 1.81(6) 2.790(5) 167(7) 2_664 yes
O9 H16 O8 0.94(2) 2.16(2) 3.097(6) 172(7) . yes

_refine_diff_density_max         0.566
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_compound6
_database_code_depnum_ccdc_archive 'CCDC 1857657'
_audit_update_record             
;
2019-01-03 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H48 N6 Na2 O14 S2'
_chemical_formula_sum            'C44 H48 N6 Na2 O14 S2'
_chemical_formula_weight         994.98

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'
Na Na 0.0362 0.0249 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   7.3204(13)
_cell_length_b                   12.411(2)
_cell_length_c                   13.597(2)
_cell_angle_alpha                86.394(9)
_cell_angle_beta                 75.139(9)
_cell_angle_gamma                75.607(10)
_cell_volume                     1156.6(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9891
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      25.26

_exptl_crystal_description       Rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.208
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32097
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.295
_diffrn_reflns_theta_max         25.441
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4257
_reflns_number_gt                3262
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury CSD 3.10.3'
_computing_publication_material  
'SHELXL-2018/3 (Sheldrick, 2018), WinGX (Farrugia, 2012)'
_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)+(0.0525P)²+0.6113P] 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         4257
_refine_ls_number_parameters     322
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.012
_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
S1 S 0.31915(8) 0.18770(4) 0.45502(4) 0.02866(16) Uani 1 1 d . . . . .
Na1 Na 0.76261(13) 0.01117(7) 0.33885(7) 0.0383(2) Uani 1 1 d . . . . .
O3 O 0.6494(2) -0.12517(11) 0.45455(11) 0.0341(4) Uani 1 1 d . . . . .
O4 O 0.1338(2) 0.18457(13) 0.43602(12) 0.0404(4) Uani 1 1 d . . . . .
O5 O 0.4813(2) 0.15509(13) 0.36771(12) 0.0456(4) Uani 1 1 d . . . . .
O2 O 0.7133(2) -0.11483(13) 0.23511(11) 0.0403(4) Uani 1 1 d . . . . .
N7 N 0.7055(3) -0.30045(15) 0.34037(13) 0.0309(4) Uani 1 1 d D . . . .
C12 C 0.7033(3) -0.33099(16) 0.52049(15) 0.0259(4) Uani 1 1 d . . . . .
N9 N 0.7230(3) -0.34570(15) 0.25318(13) 0.0326(4) Uani 1 1 d . . . . .
N10 N 0.7196(3) -0.12101(17) 0.06787(14) 0.0406(5) Uani 1 1 d D . . . .
O6 O 0.9510(3) 0.14246(15) 0.28778(15) 0.0564(5) Uani 1 1 d D . . . .
O7 O 1.0503(3) -0.09098(19) 0.38043(17) 0.0664(6) Uani 1 1 d D . . . .
C18 C 0.7591(3) -0.52413(18) 0.58394(17) 0.0327(5) Uani 1 1 d . . . . .
C13 C 0.7267(3) -0.40818(17) 0.60222(15) 0.0284(5) Uani 1 1 d . . . . .
O1 O 0.7833(3) -0.32519(16) -0.00703(13) 0.0609(6) Uani 1 1 d . . . . .
C11 C 0.7139(3) -0.37041(17) 0.42563(16) 0.0287(5) Uani 1 1 d . . . . .
C3 C 0.7294(3) -0.28911(19) 0.16802(16) 0.0336(5) Uani 1 1 d . . . . .
C5 C 0.7123(3) -0.0083(2) 0.04076(16) 0.0360(5) Uani 1 1 d . . . . .
C4 C 0.7201(3) -0.16757(19) 0.15950(16) 0.0332(5) Uani 1 1 d . . . . .
C17 C 0.7911(4) -0.6017(2) 0.66182(19) 0.0446(6) Uani 1 1 d . . . . .
H17 H 0.811448 -0.677122 0.649389 0.054 Uiso 1 1 calc R U . . .
C2 C 0.7559(4) -0.3611(2) 0.08003(18) 0.0417(6) Uani 1 1 d . . . . .
C14 C 0.7264(3) -0.37703(19) 0.70073(16) 0.0366(5) Uani 1 1 d . . . . .
H14 H 0.703468 -0.302064 0.715856 0.044 Uiso 1 1 calc R U . . .
C6 C 0.6157(4) 0.0787(2) 0.10757(18) 0.0436(6) Uani 1 1 d . . . . .
H6 H 0.552473 0.064630 0.173932 0.052 Uiso 1 1 calc R U . . .
C15 C 0.7590(4) -0.4548(2) 0.77398(18) 0.0449(6) Uani 1 1 d . . . . .
H15 H 0.758856 -0.431733 0.837793 0.054 Uiso 1 1 calc R U . . .
C19 C 0.7626(3) -0.55919(19) 0.48649(18) 0.0399(6) Uani 1 1 d . . . . .
H19 H 0.780840 -0.634536 0.474499 0.048 Uiso 1 1 calc R U . . .
C16 C 0.7926(4) -0.5679(2) 0.75483(19) 0.0476(6) Uani 1 1 d . . . . .
H16 H 0.815750 -0.619957 0.805229 0.057 Uiso 1 1 calc R U . . .
C20 C 0.7402(3) -0.48619(18) 0.41079(18) 0.0372(5) Uani 1 1 d . . . . .
H20 H 0.741991 -0.511773 0.347634 0.045 Uiso 1 1 calc R U . . .
C10 C 0.8012(4) 0.0141(2) -0.05891(18) 0.0472(6) Uani 1 1 d . . . . .
H10 H 0.863936 -0.043864 -0.104899 0.057 Uiso 1 1 calc R U . . .
C22 C 1.2477(4) -0.0948(3) 0.3667(3) 0.0738(10) Uani 1 1 d . . . . .
H22A H 1.283364 -0.039447 0.318056 0.111 Uiso 1 1 calc R U . . .
H22B H 1.324312 -0.167109 0.342287 0.111 Uiso 1 1 calc R U . . .
H22C H 1.271105 -0.080528 0.430440 0.111 Uiso 1 1 calc R U . . .
C7 C 0.6134(4) 0.1864(2) 0.0755(2) 0.0545(7) Uani 1 1 d . . . . .
H7 H 0.549555 0.244722 0.120941 0.065 Uiso 1 1 calc R U . . .
C1 C 0.7515(5) -0.4806(2) 0.0990(2) 0.0596(8) Uani 1 1 d . . . . .
H1A H 0.745231 -0.513013 0.038034 0.089 Uiso 1 1 calc R U . . .
H1B H 0.639272 -0.485545 0.152532 0.089 Uiso 1 1 calc R U . . .
H1C H 0.867325 -0.519985 0.118581 0.089 Uiso 1 1 calc R U . . .
C21 C 0.8874(5) 0.2493(2) 0.2483(3) 0.0678(9) Uani 1 1 d . . . . .
H21A H 0.888759 0.243027 0.178079 0.102 Uiso 1 1 calc R U . . .
H21B H 0.972704 0.294954 0.253791 0.102 Uiso 1 1 calc R U . . .
H21C H 0.757354 0.282645 0.286164 0.102 Uiso 1 1 calc R U . . .
C8 C 0.7034(4) 0.2091(2) -0.0223(2) 0.0587(7) Uani 1 1 d . . . . .
H8 H 0.701826 0.282183 -0.042887 0.070 Uiso 1 1 calc R U . . .
C9 C 0.7960(4) 0.1229(3) -0.0895(2) 0.0565(7) Uani 1 1 d . . . . .
H9 H 0.855864 0.137781 -0.156244 0.068 Uiso 1 1 calc R U . . .
H10A H 0.737(5) -0.170(2) 0.019(2) 0.085 Uiso 1 1 d D U . . .
H7A H 0.700(5) -0.2281(16) 0.342(3) 0.085 Uiso 1 1 d D U . . .
H6A H 1.018(5) 0.149(3) 0.331(2) 0.085 Uiso 1 1 d D U . . .
H7B H 1.004(5) -0.113(3) 0.4430(16) 0.085 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O5 1.4425(16) . ?
S1 O3 1.4503(15) 2_656 ?
S1 O4 1.4551(17) . ?
S1 C12 1.789(2) 2_656 ?
Na1 O2 2.3203(18) . ?
Na1 O5 2.3304(18) . ?
Na1 O6 2.350(2) . ?
Na1 O7 2.357(2) . ?
Na1 O3 2.3913(17) . ?
Na1 H7B 2.68(3) . ?
O2 C4 1.237(3) . ?
N7 N9 1.307(2) . ?
N7 C11 1.409(3) . ?
N7 H7A 0.891(18) . ?
C12 C11 1.385(3) . ?
C12 C13 1.437(3) . ?
N9 C3 1.312(3) . ?
N10 C4 1.341(3) . ?
N10 C5 1.416(3) . ?
N10 H10A 0.886(18) . ?
O6 C21 1.413(3) . ?
O6 H6A 0.877(18) . ?
O7 C22 1.398(3) . ?
O7 H7B 0.886(18) . ?
C18 C17 1.410(3) . ?
C18 C19 1.413(3) . ?
C18 C13 1.426(3) . ?
C13 C14 1.416(3) . ?
O1 C2 1.223(3) . ?
C11 C20 1.422(3) . ?
C3 C2 1.482(3) . ?
C3 C4 1.491(3) . ?
C5 C6 1.380(3) . ?
C5 C10 1.388(3) . ?
C17 C16 1.361(4) . ?
C17 H17 0.9300 . ?
C2 C1 1.497(4) . ?
C14 C15 1.366(3) . ?
C14 H14 0.9300 . ?
C6 C7 1.377(4) . ?
C6 H6 0.9300 . ?
C15 C16 1.394(4) . ?
C15 H15 0.9300 . ?
C19 C20 1.343(3) . ?
C19 H19 0.9300 . ?
C16 H16 0.9300 . ?
C20 H20 0.9300 . ?
C10 C9 1.381(4) . ?
C10 H10 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C7 C8 1.370(4) . ?
C7 H7 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C8 C9 1.373(4) . ?
C8 H8 0.9300 . ?
C9 H9 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
O5 S1 O3 112.30(10) . 2_656 ?
O5 S1 O4 112.96(11) . . ?
O3 S1 O4 111.50(9) 2_656 . ?
O5 S1 C12 107.10(10) . 2_656 ?
O3 S1 C12 107.63(9) 2_656 2_656 ?
O4 S1 C12 104.81(9) . 2_656 ?
O2 Na1 O5 105.58(7) . . ?
O2 Na1 O6 126.70(7) . . ?
O5 Na1 O6 89.54(7) . . ?
O2 Na1 O7 100.93(8) . . ?
O5 Na1 O7 152.01(9) . . ?
O6 Na1 O7 81.67(8) . . ?
O2 Na1 O3 75.93(6) . . ?
O5 Na1 O3 100.13(6) . . ?
O6 Na1 O3 152.14(7) . . ?
O7 Na1 O3 77.61(7) . . ?
O2 Na1 H7B 104.3(8) . . ?
O5 Na1 H7B 139.1(6) . . ?
O6 Na1 H7B 94.4(7) . . ?
O7 Na1 H7B 18.9(5) . . ?
O3 Na1 H7B 61.4(6) . . ?
S1 O3 Na1 142.31(10) 2_656 . ?
S1 O5 Na1 133.07(10) . . ?
C4 O2 Na1 162.13(15) . . ?
N9 N7 C11 118.27(18) . . ?
N9 N7 H7A 119(2) . . ?
C11 N7 H7A 123(2) . . ?
C11 C12 C13 119.57(18) . . ?
C11 C12 S1 123.05(16) . 2_656 ?
C13 C12 S1 117.18(15) . 2_656 ?
N7 N9 C3 123.10(19) . . ?
C4 N10 C5 127.42(19) . . ?
C4 N10 H10A 113(2) . . ?
C5 N10 H10A 119(2) . . ?
C21 O6 Na1 125.69(18) . . ?
C21 O6 H6A 108(2) . . ?
Na1 O6 H6A 113(2) . . ?
C22 O7 Na1 143.26(19) . . ?
C22 O7 H7B 109(2) . . ?
Na1 O7 H7B 101(2) . . ?
C17 C18 C19 121.2(2) . . ?
C17 C18 C13 120.0(2) . . ?
C19 C18 C13 118.8(2) . . ?
C14 C13 C18 116.83(19) . . ?
C14 C13 C12 124.05(19) . . ?
C18 C13 C12 119.08(19) . . ?
C12 C11 N7 122.63(18) . . ?
C12 C11 C20 119.92(19) . . ?
N7 C11 C20 117.42(19) . . ?
N9 C3 C2 112.1(2) . . ?
N9 C3 C4 124.18(19) . . ?
C2 C3 C4 123.7(2) . . ?
C6 C5 C10 119.5(2) . . ?
C6 C5 N10 122.9(2) . . ?
C10 C5 N10 117.5(2) . . ?
O2 C4 N10 123.2(2) . . ?
O2 C4 C3 119.85(19) . . ?
N10 C4 C3 116.90(19) . . ?
C16 C17 C18 121.1(2) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
O1 C2 C3 121.5(2) . . ?
O1 C2 C1 119.8(2) . . ?
C3 C2 C1 118.7(2) . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C7 C6 C5 119.7(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C14 C15 C16 121.2(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C20 C19 C18 121.5(2) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C19 C20 C11 121.0(2) . . ?
C19 C20 H20 119.5 . . ?
C11 C20 H20 119.5 . . ?
C9 C10 C5 119.8(2) . . ?
C9 C10 H10 120.1 . . ?
C5 C10 H10 120.1 . . ?
O7 C22 H22A 109.5 . . ?
O7 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O7 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O6 C21 H21A 109.5 . . ?
O6 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O6 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C7 C8 C9 119.2(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 O5 Na1 8.11(18) 2_656 . . . ?
O4 S1 O5 Na1 -119.06(14) . . . . ?
C12 S1 O5 Na1 126.06(14) 2_656 . . . ?
C11 N7 N9 C3 -175.66(19) . . . . ?
C17 C18 C13 C14 -0.7(3) . . . . ?
C19 C18 C13 C14 -179.4(2) . . . . ?
C17 C18 C13 C12 177.2(2) . . . . ?
C19 C18 C13 C12 -1.4(3) . . . . ?
C11 C12 C13 C14 177.3(2) . . . . ?
S1 C12 C13 C14 2.2(3) 2_656 . . . ?
C11 C12 C13 C18 -0.5(3) . . . . ?
S1 C12 C13 C18 -175.55(15) 2_656 . . . ?
C13 C12 C11 N7 -175.56(18) . . . . ?
S1 C12 C11 N7 -0.8(3) 2_656 . . . ?
C13 C12 C11 C20 2.5(3) . . . . ?
S1 C12 C11 C20 177.22(16) 2_656 . . . ?
N9 N7 C11 C12 177.83(19) . . . . ?
N9 N7 C11 C20 -0.2(3) . . . . ?
N7 N9 C3 C2 178.20(19) . . . . ?
N7 N9 C3 C4 0.8(3) . . . . ?
C4 N10 C5 C6 -32.0(4) . . . . ?
C4 N10 C5 C10 150.4(2) . . . . ?
Na1 O2 C4 N10 -37.8(6) . . . . ?
Na1 O2 C4 C3 142.2(4) . . . . ?
C5 N10 C4 O2 0.2(4) . . . . ?
C5 N10 C4 C3 -179.7(2) . . . . ?
N9 C3 C4 O2 2.9(3) . . . . ?
C2 C3 C4 O2 -174.2(2) . . . . ?
N9 C3 C4 N10 -177.1(2) . . . . ?
C2 C3 C4 N10 5.8(3) . . . . ?
C19 C18 C17 C16 178.3(2) . . . . ?
C13 C18 C17 C16 -0.3(4) . . . . ?
N9 C3 C2 O1 -173.1(2) . . . . ?
C4 C3 C2 O1 4.3(4) . . . . ?
N9 C3 C2 C1 6.0(3) . . . . ?
C4 C3 C2 C1 -176.5(2) . . . . ?
C18 C13 C14 C15 1.1(3) . . . . ?
C12 C13 C14 C15 -176.7(2) . . . . ?
C10 C5 C6 C7 -1.9(4) . . . . ?
N10 C5 C6 C7 -179.4(2) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C17 C18 C19 C20 -177.3(2) . . . . ?
C13 C18 C19 C20 1.4(3) . . . . ?
C18 C17 C16 C15 1.0(4) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C18 C19 C20 C11 0.6(4) . . . . ?
C12 C11 C20 C19 -2.6(3) . . . . ?
N7 C11 C20 C19 175.5(2) . . . . ?
C6 C5 C10 C9 1.6(4) . . . . ?
N10 C5 C10 C9 179.2(2) . . . . ?
C5 C6 C7 C8 0.8(4) . . . . ?
C6 C7 C8 C9 0.6(5) . . . . ?
C7 C8 C9 C10 -0.9(5) . . . . ?
C5 C10 C9 C8 -0.2(4) . . . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_compound5
_database_code_depnum_ccdc_archive 'CCDC 1857656'
_audit_update_record             
;
2019-01-03 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H28 Cu N6 O16 S2'
_chemical_formula_sum            'C20 H28 Cu N6 O16 S2'
_chemical_formula_weight         736.14

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'
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                   7.0948(7)
_cell_length_b                   13.2858(11)
_cell_length_c                   16.1728(15)
_cell_angle_alpha                90
_cell_angle_beta                 100.556(3)
_cell_angle_gamma                90
_cell_volume                     1498.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8539
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      25.37

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_F_000             758
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.951
_shelx_estimated_absorpt_T_min   0.696
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25305
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.562
_diffrn_reflns_theta_max         25.431
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2782
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury CSD 3.10.3'
_computing_publication_material  
'SHELXL-2018/3 (Sheldrick, 2018), WinGX (Farrugia, 2012)'
_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)+(0.0339P)²+5.0727P] 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         2782
_refine_ls_number_parameters     230
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1234
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.047
_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 1.000000 0.500000 0.500000 0.0280(2) Uani 1 2 d S . P . .
S1 S 0.57221(15) 0.36121(7) 0.42056(7) 0.0282(3) Uani 1 1 d . . . . .
O4 O 0.7679(4) 0.3941(2) 0.4200(2) 0.0408(8) Uani 1 1 d . . . . .
O6 O 0.4329(5) 0.4165(2) 0.35973(19) 0.0417(8) Uani 1 1 d . . . . .
O1 O 0.6403(5) -0.0547(2) 0.3066(2) 0.0457(9) Uani 1 1 d D . . . .
O3 O 0.8788(5) -0.1910(2) 0.50082(19) 0.0415(8) Uani 1 1 d . . . . .
N2 N 0.7810(5) 0.0038(3) 0.5488(2) 0.0295(8) Uani 1 1 d . . . . .
N1 N 0.7331(5) -0.0145(2) 0.4689(2) 0.0291(8) Uani 1 1 d D . . . .
O2 O 0.9696(5) -0.0859(3) 0.74808(19) 0.0462(8) Uani 1 1 d . . . . .
O8 O 0.8303(5) 0.6135(2) 0.4558(2) 0.0371(7) Uani 1 1 d D . . . .
O5 O 0.5239(5) 0.3618(2) 0.50369(19) 0.0396(8) Uani 1 1 d . . . . .
O7 O 1.1156(5) 0.5097(3) 0.4010(2) 0.0513(9) Uani 1 1 d D . . . .
C6 C 0.6586(6) 0.0645(3) 0.4145(2) 0.0266(9) Uani 1 1 d . . . . .
N3 N 0.9710(6) -0.2346(3) 0.6368(3) 0.0432(10) Uani 1 1 d . . . . .
C8 C 0.9012(6) -0.0297(3) 0.6896(3) 0.0359(10) Uani 1 1 d . . . . .
C4 C 0.5659(6) 0.2356(3) 0.3852(3) 0.0275(9) Uani 1 1 d . . . . .
C5 C 0.6353(6) 0.1619(3) 0.4427(3) 0.0279(9) Uani 1 1 d . . . . .
H3 H 0.666313 0.177085 0.499719 0.033 Uiso 1 1 calc R U . . .
C9 C 0.9033(6) -0.1685(3) 0.5773(3) 0.0307(9) Uani 1 1 d . . . . .
C7 C 0.8578(6) -0.0659(3) 0.6026(3) 0.0282(9) Uani 1 1 d . . . . .
C1 C 0.6102(6) 0.0418(3) 0.3290(3) 0.0311(9) Uani 1 1 d . . . . .
C3 C 0.5144(7) 0.2129(3) 0.3000(3) 0.0366(10) Uani 1 1 d . . . . .
H2 H 0.465742 0.262975 0.261813 0.044 Uiso 1 1 calc R U . . .
C10 C 0.8632(9) 0.0784(4) 0.7076(3) 0.0590(15) Uani 1 1 d . . . . .
H10A H 0.856506 0.085875 0.766065 0.088 Uiso 1 1 calc R U . . .
H10B H 0.743744 0.098953 0.673842 0.088 Uiso 1 1 calc R U . . .
H10C H 0.964958 0.119546 0.694510 0.088 Uiso 1 1 calc R U . . .
C2 C 0.5356(7) 0.1159(3) 0.2722(3) 0.0370(11) Uani 1 1 d . . . . .
H1 H 0.499755 0.100501 0.215370 0.044 Uiso 1 1 calc R U . . .
H3N1 H 1.016(8) -0.291(4) 0.622(3) 0.056 Uiso 1 1 d . U . . .
H3N2 H 0.995(8) -0.212(4) 0.690(4) 0.056 Uiso 1 1 d . U . . .
H82 H 0.870(7) 0.6774(19) 0.465(3) 0.056 Uiso 1 1 d D U . . .
H81 H 0.716(4) 0.610(4) 0.470(3) 0.056 Uiso 1 1 d D U . . .
H1N H 0.751(7) -0.077(2) 0.443(3) 0.056 Uiso 1 1 d D U . . .
H71 H 1.226(4) 0.481(4) 0.397(3) 0.056 Uiso 1 1 d D U . . .
H72 H 1.061(7) 0.541(4) 0.355(2) 0.056 Uiso 1 1 d D U . . .
H1O H 0.615(7) -0.060(4) 0.2504(10) 0.056 Uiso 1 1 d D 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 O7 1.932(3) 3_766 ?
Cu1 O7 1.932(3) . ?
Cu1 O8 1.979(3) 3_766 ?
Cu1 O8 1.979(3) . ?
Cu1 O4 2.363(3) 3_766 ?
Cu1 O4 2.363(3) . ?
S1 O5 1.447(3) . ?
S1 O4 1.457(3) . ?
S1 O6 1.459(3) . ?
S1 C4 1.762(4) . ?
O1 C1 1.359(5) . ?
O1 H1O 0.896(14) . ?
O3 C9 1.252(5) . ?
N2 N1 1.299(5) . ?
N2 C7 1.317(5) . ?
N1 C6 1.407(5) . ?
N1 H1N 0.944(19) . ?
O2 C8 1.233(5) . ?
O8 H82 0.90(2) . ?
O8 H81 0.88(2) . ?
O7 H71 0.889(14) . ?
O7 H72 0.88(2) . ?
C6 C5 1.392(6) . ?
C6 C1 1.395(6) . ?
N3 C9 1.326(6) . ?
N3 H3N1 0.86(6) . ?
N3 H3N2 0.90(6) . ?
C8 C7 1.465(6) . ?
C8 C10 1.499(7) . ?
C4 C5 1.378(6) . ?
C4 C3 1.393(6) . ?
C5 H3 0.9300 . ?
C9 C7 1.477(6) . ?
C1 C2 1.385(6) . ?
C3 C2 1.382(6) . ?
C3 H2 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C2 H1 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
O7 Cu1 O7 180.0 3_766 . ?
O7 Cu1 O8 88.44(14) 3_766 3_766 ?
O7 Cu1 O8 91.56(14) . 3_766 ?
O7 Cu1 O8 91.56(14) 3_766 . ?
O7 Cu1 O8 88.44(14) . . ?
O8 Cu1 O8 180.0 3_766 . ?
O7 Cu1 O4 86.86(14) 3_766 3_766 ?
O7 Cu1 O4 93.14(14) . 3_766 ?
O8 Cu1 O4 86.51(12) 3_766 3_766 ?
O8 Cu1 O4 93.49(12) . 3_766 ?
O7 Cu1 O4 93.14(14) 3_766 . ?
O7 Cu1 O4 86.86(14) . . ?
O8 Cu1 O4 93.49(12) 3_766 . ?
O8 Cu1 O4 86.51(12) . . ?
O4 Cu1 O4 180.0 3_766 . ?
O5 S1 O4 113.1(2) . . ?
O5 S1 O6 112.15(19) . . ?
O4 S1 O6 111.9(2) . . ?
O5 S1 C4 108.10(19) . . ?
O4 S1 C4 104.47(19) . . ?
O6 S1 C4 106.53(19) . . ?
S1 O4 Cu1 138.11(19) . . ?
C1 O1 H1O 109(4) . . ?
N1 N2 C7 121.9(3) . . ?
N2 N1 C6 118.9(3) . . ?
N2 N1 H1N 125(3) . . ?
C6 N1 H1N 116(3) . . ?
Cu1 O8 H82 121(3) . . ?
Cu1 O8 H81 113(4) . . ?
H82 O8 H81 106(5) . . ?
Cu1 O7 H71 124(4) . . ?
Cu1 O7 H72 123(4) . . ?
H71 O7 H72 114(5) . . ?
C5 C6 C1 120.2(4) . . ?
C5 C6 N1 122.8(4) . . ?
C1 C6 N1 117.0(3) . . ?
C9 N3 H3N1 119(4) . . ?
C9 N3 H3N2 117(3) . . ?
H3N1 N3 H3N2 122(5) . . ?
O2 C8 C7 121.5(4) . . ?
O2 C8 C10 119.4(4) . . ?
C7 C8 C10 119.1(4) . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 S1 118.0(3) . . ?
C3 C4 S1 120.9(3) . . ?
C4 C5 C6 119.3(4) . . ?
C4 C5 H3 120.4 . . ?
C6 C5 H3 120.4 . . ?
O3 C9 N3 121.7(4) . . ?
O3 C9 C7 119.7(4) . . ?
N3 C9 C7 118.6(4) . . ?
N2 C7 C8 113.1(4) . . ?
N2 C7 C9 123.4(4) . . ?
C8 C7 C9 123.5(4) . . ?
O1 C1 C2 123.6(4) . . ?
O1 C1 C6 116.5(4) . . ?
C2 C1 C6 119.9(4) . . ?
C2 C3 C4 120.0(4) . . ?
C2 C3 H2 120.0 . . ?
C4 C3 H2 120.0 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H1 120.1 . . ?
C1 C2 H1 120.1 . . ?

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
O5 S1 O4 Cu1 -27.6(4) . . . . ?
O6 S1 O4 Cu1 100.2(3) . . . . ?
C4 S1 O4 Cu1 -144.9(3) . . . . ?
C7 N2 N1 C6 -177.5(4) . . . . ?
N2 N1 C6 C5 0.5(6) . . . . ?
N2 N1 C6 C1 179.6(4) . . . . ?
O5 S1 C4 C5 -39.0(4) . . . . ?
O4 S1 C4 C5 81.7(4) . . . . ?
O6 S1 C4 C5 -159.7(3) . . . . ?
O5 S1 C4 C3 148.8(4) . . . . ?
O4 S1 C4 C3 -90.6(4) . . . . ?
O6 S1 C4 C3 28.0(4) . . . . ?
C3 C4 C5 C6 1.7(6) . . . . ?
S1 C4 C5 C6 -170.6(3) . . . . ?
C1 C6 C5 C4 -0.6(6) . . . . ?
N1 C6 C5 C4 178.4(4) . . . . ?
N1 N2 C7 C8 180.0(4) . . . . ?
N1 N2 C7 C9 2.5(6) . . . . ?
O2 C8 C7 N2 178.4(4) . . . . ?
C10 C8 C7 N2 -2.3(6) . . . . ?
O2 C8 C7 C9 -4.2(7) . . . . ?
C10 C8 C7 C9 175.2(4) . . . . ?
O3 C9 C7 N2 4.0(7) . . . . ?
N3 C9 C7 N2 -176.5(4) . . . . ?
O3 C9 C7 C8 -173.2(4) . . . . ?
N3 C9 C7 C8 6.3(6) . . . . ?
C5 C6 C1 O1 179.0(4) . . . . ?
N1 C6 C1 O1 -0.1(6) . . . . ?
C5 C6 C1 C2 -1.2(7) . . . . ?
N1 C6 C1 C2 179.8(4) . . . . ?
C5 C4 C3 C2 -1.0(7) . . . . ?
S1 C4 C3 C2 171.1(4) . . . . ?
C4 C3 C2 C1 -0.8(7) . . . . ?
O1 C1 C2 C3 -178.3(4) . . . . ?
C6 C1 C2 C3 1.9(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3N1 O4 0.86(6) 2.25(6) 3.065(5) 157(5) 3_756 yes
N3 H3N2 O2 0.90(6) 1.94(6) 2.674(6) 137(5) . yes
O8 H82 O3 0.90(2) 1.84(3) 2.703(4) 160(5) 1_565 yes
O8 H81 S1 0.88(2) 2.97(3) 3.789(3) 156(4) 3_666 yes
O8 H81 O5 0.88(2) 1.87(2) 2.730(4) 166(5) 3_666 yes
N1 H1N O3 0.944(19) 1.92(4) 2.577(4) 125(4) . yes
O7 H71 S1 0.889(14) 2.89(2) 3.756(3) 166(5) 1_655 yes
O7 H71 O6 0.889(14) 1.88(2) 2.756(5) 166(5) 1_655 yes
O7 H72 O2 0.88(2) 1.83(2) 2.698(4) 168(5) 4_565 yes
O1 H1O S1 0.896(14) 3.03(2) 3.872(3) 158(4) 2_645 yes
O1 H1O O6 0.896(14) 1.779(16) 2.672(4) 174(5) 2_645 yes

_refine_diff_density_max         1.367
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.093

