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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1028077'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C18 H14 Cu N6 O3 S), 3(C H4 O)'
_chemical_formula_sum            'C75 H68 Cu4 N24 O15 S4'
_chemical_formula_weight         1928.01

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   16.3302(4)
_cell_length_b                   20.2955(5)
_cell_length_c                   25.5819(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.3830(10)
_cell_angle_gamma                90.00
_cell_volume                     8091.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      25.73

_exptl_crystal_description       Prism
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3944
_exptl_absorpt_coefficient_mu    1.222
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6532
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            57693
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.30
_diffrn_reflns_theta_max         25.75
_reflns_number_total             15443
_reflns_number_gt                10120
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
The restraints used during structure refinement in this complex are DFIX, OMIT. 
DFIX is used to fix distance of proton
 of -NH group to its N atom and to fix carbon to oxygen atom in 
lattice metanol solvent. OMIT command is used to suppresses
 all unnecessary reflections those who are truncated by beam stop.
 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         15443
_refine_ls_number_parameters     1126
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.2377
_refine_ls_wR_factor_gt          0.1733
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_restrained_S_all      0.888
_refine_ls_shift/su_max          0.005
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3648(4) 0.7598(3) 0.4320(2) 0.0401(15) Uani 1 1 d . . .
H1 H 0.3443 0.7997 0.4430 0.048 Uiso 1 1 calc R . .
C2 C 0.3420(5) 0.7002(4) 0.4507(3) 0.060(2) Uani 1 1 d . . .
H2 H 0.3052 0.6992 0.4733 0.072 Uiso 1 1 calc R . .
C3 C 0.3739(6) 0.6424(4) 0.4359(3) 0.060(2) Uani 1 1 d . . .
H3 H 0.3622 0.6012 0.4497 0.072 Uiso 1 1 calc R . .
C4 C 0.4224(5) 0.6459(3) 0.4008(3) 0.0463(17) Uani 1 1 d . . .
H4 H 0.4435 0.6067 0.3891 0.056 Uiso 1 1 calc R . .
C5 C 0.4410(4) 0.7066(3) 0.3823(2) 0.0344(14) Uani 1 1 d . . .
C6 C 0.4889(4) 0.7148(3) 0.3407(2) 0.0329(13) Uani 1 1 d . . .
C7 C 0.5051(5) 0.6631(3) 0.3106(3) 0.0522(19) Uani 1 1 d . . .
H7 H 0.4887 0.6195 0.3166 0.063 Uiso 1 1 calc R . .
C8 C 0.5460(5) 0.6760(3) 0.2712(3) 0.056(2) Uani 1 1 d . . .
H8 H 0.5599 0.6406 0.2510 0.067 Uiso 1 1 calc R . .
C9 C 0.5661(4) 0.7388(3) 0.2613(3) 0.0467(17) Uani 1 1 d . . .
H9 H 0.5924 0.7483 0.2337 0.056 Uiso 1 1 calc R . .
C10 C 0.5469(4) 0.7886(3) 0.2929(2) 0.0375(14) Uani 1 1 d . . .
H10 H 0.5606 0.8326 0.2863 0.045 Uiso 1 1 calc R . .
C11 C 0.5964(3) 0.8736(3) 0.47868(19) 0.0231(11) Uani 1 1 d . . .
C12 C 0.6777(4) 0.8622(3) 0.5169(2) 0.0293(13) Uani 1 1 d . . .
H12 H 0.7234 0.8472 0.5042 0.035 Uiso 1 1 calc R . .
C13 C 0.6925(3) 0.8722(3) 0.5724(2) 0.0277(12) Uani 1 1 d . . .
H13 H 0.7473 0.8637 0.5977 0.033 Uiso 1 1 calc R . .
C14 C 0.6258(4) 0.8949(2) 0.5905(2) 0.0254(12) Uani 1 1 d . . .
C15 C 0.5475(4) 0.9128(2) 0.5547(2) 0.0241(12) Uani 1 1 d . . .
H15 H 0.5048 0.9318 0.5684 0.029 Uiso 1 1 calc R . .
C16 C 0.5310(3) 0.9029(2) 0.4983(2) 0.0222(11) Uani 1 1 d . . .
C17 C 0.4490(3) 0.9249(2) 0.4631(2) 0.0225(11) Uani 1 1 d . . .
H17 H 0.4133 0.9491 0.4795 0.027 Uiso 1 1 calc R . .
C18 C 0.3196(3) 0.9347(3) 0.32988(19) 0.0231(11) Uani 1 1 d . . .
C19 C 0.1334(4) 0.6843(3) 0.3191(2) 0.0301(13) Uani 1 1 d . . .
H19 H 0.1324 0.6382 0.3127 0.036 Uiso 1 1 calc R . .
C20 C 0.1874(4) 0.7228(3) 0.2999(2) 0.0387(15) Uani 1 1 d . . .
H20 H 0.2227 0.7039 0.2803 0.046 Uiso 1 1 calc R . .
C21 C 0.1891(4) 0.7899(3) 0.3101(3) 0.0425(16) Uani 1 1 d . . .
H21 H 0.2258 0.8178 0.2973 0.051 Uiso 1 1 calc R . .
C22 C 0.1378(4) 0.8162(3) 0.3385(2) 0.0359(14) Uani 1 1 d . . .
H22 H 0.1395 0.8620 0.3461 0.043 Uiso 1 1 calc R . .
C23 C 0.0832(3) 0.7749(3) 0.3562(2) 0.0246(12) Uani 1 1 d . . .
C24 C 0.0281(4) 0.7981(3) 0.3883(2) 0.0271(12) Uani 1 1 d . . .
C25 C 0.0088(4) 0.8641(3) 0.3940(3) 0.0371(14) Uani 1 1 d . . .
H25 H 0.0307 0.8972 0.3755 0.045 Uiso 1 1 calc R . .
C26 C -0.0422(4) 0.8818(3) 0.4265(3) 0.0393(15) Uani 1 1 d . . .
H26 H -0.0539 0.9269 0.4315 0.047 Uiso 1 1 calc R . .
C27 C -0.0756(4) 0.8328(3) 0.4514(3) 0.0383(15) Uani 1 1 d . . .
H27 H -0.1110 0.8433 0.4737 0.046 Uiso 1 1 calc R . .
C28 C -0.0562(4) 0.7677(3) 0.4430(2) 0.0340(14) Uani 1 1 d . . .
H28 H -0.0792 0.7337 0.4600 0.041 Uiso 1 1 calc R . .
C29 C 0.1201(3) 0.6076(2) 0.4840(2) 0.0225(11) Uani 1 1 d . . .
C30 C 0.2010(3) 0.6041(3) 0.5236(2) 0.0265(12) Uani 1 1 d . . .
H30 H 0.2506 0.6117 0.5123 0.032 Uiso 1 1 calc R . .
C31 C 0.2116(3) 0.5904(3) 0.5775(2) 0.0263(12) Uani 1 1 d . . .
H31 H 0.2672 0.5891 0.6033 0.032 Uiso 1 1 calc R . .
C32 C 0.1387(4) 0.5781(3) 0.59366(19) 0.0242(12) Uani 1 1 d . . .
C33 C 0.0574(3) 0.5771(2) 0.5568(2) 0.0233(11) Uani 1 1 d . . .
H33 H 0.0093 0.5663 0.5688 0.028 Uiso 1 1 calc R . .
C34 C 0.0459(3) 0.5918(2) 0.50155(19) 0.0194(11) Uani 1 1 d . . .
C35 C -0.0398(3) 0.5846(2) 0.46441(19) 0.0204(11) Uani 1 1 d . . .
H35 H -0.0824 0.5668 0.4788 0.025 Uiso 1 1 calc R . .
C36 C -0.1692(3) 0.6019(2) 0.33204(19) 0.0204(11) Uani 1 1 d . . .
C37 C 0.3846(4) 0.8212(3) 0.1659(2) 0.0327(13) Uani 1 1 d . . .
H37 H 0.3691 0.8550 0.1868 0.039 Uiso 1 1 calc R . .
C38 C 0.3502(4) 0.7595(4) 0.1661(3) 0.0515(18) Uani 1 1 d . . .
H38 H 0.3108 0.7514 0.1862 0.062 Uiso 1 1 calc R . .
C39 C 0.3733(5) 0.7092(4) 0.1367(3) 0.058(2) Uani 1 1 d . . .
H39 H 0.3507 0.6660 0.1369 0.070 Uiso 1 1 calc R . .
C40 C 0.4296(4) 0.7229(3) 0.1072(3) 0.0465(17) Uani 1 1 d . . .
H40 H 0.4470 0.6892 0.0870 0.056 Uiso 1 1 calc R . .
C41 C 0.4609(4) 0.7876(3) 0.1076(2) 0.0327(13) Uani 1 1 d . . .
C42 C 0.5183(4) 0.8072(3) 0.0759(2) 0.0289(13) Uani 1 1 d . . .
C43 C 0.5421(4) 0.7661(3) 0.0395(2) 0.0379(15) Uani 1 1 d . . .
H43 H 0.5222 0.7218 0.0346 0.045 Uiso 1 1 calc R . .
C44 C 0.5955(4) 0.7901(3) 0.0104(2) 0.0408(16) Uani 1 1 d . . .
H44 H 0.6128 0.7621 -0.0141 0.049 Uiso 1 1 calc R . .
C45 C 0.6226(4) 0.8535(3) 0.0170(3) 0.0407(16) Uani 1 1 d . . .
H45 H 0.6587 0.8705 -0.0028 0.049 Uiso 1 1 calc R . .
C46 C 0.5965(4) 0.8929(3) 0.0533(2) 0.0337(14) Uani 1 1 d . . .
H46 H 0.6148 0.9376 0.0576 0.040 Uiso 1 1 calc R . .
C47 C 0.6214(3) 0.9352(3) 0.2418(2) 0.0247(12) Uani 1 1 d . . .
C48 C 0.7008(4) 0.9165(3) 0.2810(2) 0.0297(13) Uani 1 1 d . . .
H48 H 0.7417 0.8925 0.2689 0.036 Uiso 1 1 calc R . .
C49 C 0.7195(4) 0.9320(3) 0.3349(2) 0.0306(13) Uani 1 1 d . . .
H49 H 0.7728 0.9197 0.3601 0.037 Uiso 1 1 calc R . .
C50 C 0.6582(3) 0.9667(3) 0.3527(2) 0.0267(12) Uani 1 1 d . . .
C51 C 0.5812(3) 0.9860(3) 0.3167(2) 0.0249(12) Uani 1 1 d . . .
H51 H 0.5414 1.0096 0.3300 0.030 Uiso 1 1 calc R . .
C52 C 0.5607(3) 0.9715(2) 0.2613(2) 0.0220(11) Uani 1 1 d . . .
C53 C 0.4801(3) 0.9960(2) 0.2262(2) 0.0228(11) Uani 1 1 d . . .
H53 H 0.4438 1.0185 0.2432 0.027 Uiso 1 1 calc R . .
C54 C 0.3577(3) 1.0221(2) 0.0932(2) 0.0241(11) Uani 1 1 d . . .
C55 C 0.1338(4) 0.6008(3) 0.0542(2) 0.0310(13) Uani 1 1 d . . .
H55 H 0.1354 0.5543 0.0502 0.037 Uiso 1 1 calc R . .
C56 C 0.1692(4) 0.6408(3) 0.0222(2) 0.0385(15) Uani 1 1 d . . .
H56 H 0.1947 0.6220 -0.0032 0.046 Uiso 1 1 calc R . .
C57 C 0.1665(4) 0.7079(3) 0.0283(2) 0.0387(15) Uani 1 1 d . . .
H57 H 0.1898 0.7363 0.0069 0.046 Uiso 1 1 calc R . .
C58 C 0.1300(4) 0.7335(3) 0.0656(2) 0.0364(14) Uani 1 1 d . . .
H58 H 0.1273 0.7799 0.0698 0.044 Uiso 1 1 calc R . .
C59 C 0.0969(3) 0.6921(3) 0.0971(2) 0.0265(12) Uani 1 1 d . . .
C60 C 0.0551(4) 0.7160(3) 0.1382(2) 0.0280(12) Uani 1 1 d . . .
C61 C 0.0614(5) 0.7815(3) 0.1552(3) 0.0441(16) Uani 1 1 d . . .
H61 H 0.0943 0.8125 0.1421 0.053 Uiso 1 1 calc R . .
C62 C 0.0180(5) 0.8001(3) 0.1920(3) 0.0490(18) Uani 1 1 d . . .
H62 H 0.0211 0.8443 0.2047 0.059 Uiso 1 1 calc R . .
C63 C -0.0297(4) 0.7538(3) 0.2100(2) 0.0379(15) Uani 1 1 d . . .
H63 H -0.0606 0.7659 0.2347 0.045 Uiso 1 1 calc R . .
C64 C -0.0315(4) 0.6902(3) 0.1917(2) 0.0339(14) Uani 1 1 d . . .
H64 H -0.0637 0.6583 0.2044 0.041 Uiso 1 1 calc R . .
C65 C 0.1484(4) 0.5383(3) 0.2407(2) 0.0264(12) Uani 1 1 d . . .
C66 C 0.2308(4) 0.5395(3) 0.2803(2) 0.0336(14) Uani 1 1 d . . .
H66 H 0.2790 0.5519 0.2690 0.040 Uiso 1 1 calc R . .
C67 C 0.2432(4) 0.5233(3) 0.3341(2) 0.0331(13) Uani 1 1 d . . .
H67 H 0.2991 0.5243 0.3595 0.040 Uiso 1 1 calc R . .
C68 C 0.1715(4) 0.5048(3) 0.3514(2) 0.0313(13) Uani 1 1 d . . .
C69 C 0.0914(4) 0.5015(3) 0.3140(2) 0.0271(12) Uani 1 1 d . . .
H69 H 0.0441 0.4883 0.3260 0.033 Uiso 1 1 calc R . .
C70 C 0.0773(4) 0.5169(2) 0.2587(2) 0.0257(12) Uani 1 1 d . . .
C71 C -0.0082(4) 0.5071(2) 0.2226(2) 0.0257(12) Uani 1 1 d . . .
H71 H -0.0498 0.4900 0.2382 0.031 Uiso 1 1 calc R . .
C72 C -0.1376(3) 0.5104(2) 0.08922(19) 0.0220(11) Uani 1 1 d . . .
C73 C 0.7304(6) 0.7363(5) 0.3815(4) 0.091(3) Uani 1 1 d . . .
H73A H 0.7512 0.7657 0.3579 0.137 Uiso 1 1 calc R . .
H73B H 0.6741 0.7186 0.3609 0.137 Uiso 1 1 calc R . .
H73C H 0.7710 0.6999 0.3939 0.137 Uiso 1 1 calc R . .
C74 C 0.8471(6) 0.7094(5) 0.5550(3) 0.090(3) Uani 1 1 d . . .
H74A H 0.8893 0.6801 0.5793 0.135 Uiso 1 1 calc R . .
H74B H 0.7993 0.7166 0.5701 0.135 Uiso 1 1 calc R . .
H74C H 0.8742 0.7517 0.5520 0.135 Uiso 1 1 calc R . .
C75 C 0.7479(6) 0.7835(6) 0.1782(5) 0.119(5) Uani 1 1 d . . .
H75A H 0.7677 0.8251 0.1667 0.179 Uiso 1 1 calc R . .
H75B H 0.7467 0.7494 0.1508 0.179 Uiso 1 1 calc R . .
H75C H 0.7872 0.7700 0.2136 0.179 Uiso 1 1 calc R . .
N1 N 0.4144(3) 0.7622(2) 0.39920(18) 0.0308(11) Uani 1 1 d . . .
N2 N 0.5102(3) 0.7778(2) 0.33217(17) 0.0253(10) Uani 1 1 d . . .
N3 N 0.6389(3) 0.9017(2) 0.64901(18) 0.0303(11) Uani 1 1 d . . .
N4 N 0.4205(3) 0.9142(2) 0.41087(16) 0.0207(9) Uani 1 1 d . . .
N5 N 0.3414(3) 0.9430(2) 0.38397(16) 0.0235(10) Uani 1 1 d . . .
N6 N 0.2448(3) 0.9609(2) 0.30030(17) 0.0294(11) Uani 1 1 d D . .
H6A H 0.234(4) 0.961(3) 0.2652(9) 0.035 Uiso 1 1 d D . .
H6B H 0.217(3) 0.978(3) 0.322(2) 0.035 Uiso 1 1 d D . .
N7 N 0.0818(3) 0.7092(2) 0.34643(17) 0.0237(10) Uani 1 1 d . . .
N8 N -0.0064(3) 0.7506(2) 0.41168(18) 0.0277(10) Uani 1 1 d . . .
N9 N 0.1494(3) 0.5643(2) 0.65080(17) 0.0267(10) Uani 1 1 d . . .
N10 N -0.0630(3) 0.6007(2) 0.41326(16) 0.0205(9) Uani 1 1 d . . .
N11 N -0.1475(3) 0.5858(2) 0.38449(16) 0.0222(9) Uani 1 1 d . . .
N12 N -0.2484(3) 0.5896(3) 0.3010(2) 0.0340(13) Uani 1 1 d . . .
H12A H -0.271(5) 0.573(4) 0.312(3) 0.041 Uiso 1 1 d . . .
H12B H -0.262(4) 0.602(3) 0.268(3) 0.041 Uiso 1 1 d . . .
N13 N 0.4386(3) 0.8354(2) 0.13766(17) 0.0283(10) Uani 1 1 d . . .
N14 N 0.5467(3) 0.8707(2) 0.08244(17) 0.0253(10) Uani 1 1 d . . .
N15 N 0.6792(3) 0.9837(2) 0.41018(18) 0.0305(11) Uani 1 1 d . . .
N16 N 0.4529(3) 0.9899(2) 0.17334(16) 0.0214(9) Uani 1 1 d . . .
N17 N 0.3765(3) 1.0227(2) 0.14732(17) 0.0238(10) Uani 1 1 d . . .
N18 N 0.2853(3) 1.0529(2) 0.06409(18) 0.0282(11) Uani 1 1 d . . .
H18A H 0.254(4) 1.065(3) 0.082(2) 0.034 Uiso 1 1 d . . .
H18B H 0.273(4) 1.045(3) 0.026(2) 0.034 Uiso 1 1 d . . .
N19 N 0.0973(3) 0.6263(2) 0.09081(17) 0.0250(10) Uani 1 1 d . . .
N20 N 0.0112(3) 0.6713(2) 0.15617(17) 0.0278(10) Uani 1 1 d . . .
N21 N 0.1834(3) 0.4884(2) 0.40785(18) 0.0309(11) Uani 1 1 d . . .
N22 N -0.0330(3) 0.5197(2) 0.17059(16) 0.0232(10) Uani 1 1 d . . .
N23 N -0.1168(3) 0.5010(2) 0.14289(16) 0.0217(9) Uani 1 1 d . . .
N24 N -0.2151(3) 0.4881(2) 0.05880(19) 0.0262(10) Uani 1 1 d . . .
H24A H -0.247(4) 0.481(3) 0.075(2) 0.031 Uiso 1 1 d . . .
H24B H -0.231(4) 0.499(3) 0.025(2) 0.031 Uiso 1 1 d . . .
O1 O 0.5845(2) 0.85645(17) 0.42807(14) 0.0263(8) Uani 1 1 d . . .
O2 O 0.7098(3) 0.8862(2) 0.68049(15) 0.0460(12) Uani 1 1 d . . .
O3 O 0.5798(3) 0.9199(2) 0.66596(15) 0.0348(10) Uani 1 1 d . . .
O4 O 0.1147(2) 0.62393(19) 0.43425(14) 0.0267(8) Uani 1 1 d . . .
O5 O 0.2229(3) 0.5670(2) 0.68315(15) 0.0388(10) Uani 1 1 d . . .
O6 O 0.0862(3) 0.55246(19) 0.66606(14) 0.0318(9) Uani 1 1 d . . .
O7 O 0.6083(2) 0.9178(2) 0.19148(14) 0.0295(9) Uani 1 1 d . . .
O8 O 0.7472(2) 0.9641(2) 0.44193(15) 0.0361(10) Uani 1 1 d . . .
O9 O 0.6281(3) 1.0184(2) 0.42585(16) 0.0454(11) Uani 1 1 d . . .
O10 O 0.1410(2) 0.55606(19) 0.19090(14) 0.0289(9) Uani 1 1 d . . .
O11 O 0.2551(2) 0.4960(2) 0.44106(15) 0.0369(10) Uani 1 1 d . . .
O12 O 0.1223(3) 0.4674(2) 0.42130(16) 0.0427(11) Uani 1 1 d . . .
O13 O 0.7231(3) 0.7705(3) 0.4257(2) 0.0670(15) Uani 1 1 d . . .
H13A H 0.6774 0.7925 0.4167 0.080 Uiso 1 1 calc R . .
O14 O 0.8169(4) 0.6812(3) 0.5041(3) 0.0794(17) Uani 1 1 d . . .
H14 H 0.7870 0.7088 0.4819 0.095 Uiso 1 1 calc R . .
O15 O 0.6736(5) 0.7910(4) 0.1825(3) 0.116(3) Uani 1 1 d . . .
H15A H 0.6620 0.8314 0.1817 0.139 Uiso 1 1 calc R . .
S1 S 0.37738(9) 0.89082(7) 0.29470(5) 0.0247(3) Uani 1 1 d . . .
S2 S -0.10021(9) 0.63956(7) 0.30050(5) 0.0283(3) Uani 1 1 d . . .
S3 S 0.41952(9) 0.98518(7) 0.05658(5) 0.0284(3) Uani 1 1 d . . .
S4 S -0.07191(9) 0.54540(7) 0.05450(5) 0.0283(3) Uani 1 1 d . . .
Cu1 Cu 0.47173(4) 0.85174(3) 0.37167(2) 0.02090(18) Uani 1 1 d . . .
Cu2 Cu 0.00918(4) 0.65038(3) 0.37871(2) 0.02027(18) Uani 1 1 d . . .
Cu3 Cu 0.50315(4) 0.93148(3) 0.13024(2) 0.02236(19) Uani 1 1 d . . .
Cu4 Cu 0.03462(4) 0.56959(3) 0.13192(2) 0.02310(19) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.332(7) . ?
C1 C2 1.391(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.381(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.366(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(8) . ?
C4 H4 0.9500 . ?
C5 N1 1.326(7) . ?
C5 C6 1.506(8) . ?
C6 N2 1.360(7) . ?
C6 C7 1.373(8) . ?
C7 C8 1.390(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.359(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(8) . ?
C9 H9 0.9500 . ?
C10 N2 1.332(7) . ?
C10 H10 0.9500 . ?
C11 O1 1.298(6) . ?
C11 C12 1.413(7) . ?
C11 C16 1.438(7) . ?
C12 C13 1.382(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(7) . ?
C14 N3 1.455(6) . ?
C15 C16 1.402(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.443(7) . ?
C17 N4 1.295(6) . ?
C17 H17 0.9500 . ?
C18 N5 1.333(6) . ?
C18 N6 1.340(7) . ?
C18 S1 1.731(5) . ?
C19 N7 1.343(7) . ?
C19 C20 1.374(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.369(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.395(8) . ?
C22 H22 0.9500 . ?
C23 N7 1.356(7) . ?
C23 C24 1.464(8) . ?
C24 N8 1.345(7) . ?
C24 C25 1.395(8) . ?
C25 C26 1.390(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.378(9) . ?
C26 H26 0.9500 . ?
C27 C28 1.392(8) . ?
C27 H27 0.9500 . ?
C28 N8 1.346(7) . ?
C28 H28 0.9500 . ?
C29 O4 1.292(6) . ?
C29 C30 1.406(7) . ?
C29 C34 1.449(7) . ?
C30 C31 1.367(7) . ?
C30 H30 0.9500 . ?
C31 C32 1.395(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.380(7) . ?
C32 N9 1.447(6) . ?
C33 C34 1.401(7) . ?
C33 H33 0.9500 . ?
C34 C35 1.445(7) . ?
C35 N10 1.291(6) . ?
C35 H35 0.9500 . ?
C36 N11 1.322(6) . ?
C36 N12 1.325(7) . ?
C36 S2 1.745(5) . ?
C37 N13 1.328(7) . ?
C37 C38 1.372(9) . ?
C37 H37 0.9500 . ?
C38 C39 1.385(9) . ?
C38 H38 0.9500 . ?
C39 C40 1.382(9) . ?
C39 H39 0.9500 . ?
C40 C41 1.408(9) . ?
C40 H40 0.9500 . ?
C41 N13 1.355(7) . ?
C41 C42 1.467(8) . ?
C42 N14 1.363(7) . ?
C42 C43 1.389(8) . ?
C43 C44 1.393(8) . ?
C43 H43 0.9500 . ?
C44 C45 1.354(9) . ?
C44 H44 0.9500 . ?
C45 C46 1.386(8) . ?
C45 H45 0.9500 . ?
C46 N14 1.335(7) . ?
C46 H46 0.9500 . ?
C47 O7 1.289(6) . ?
C47 C48 1.433(7) . ?
C47 C52 1.440(7) . ?
C48 C49 1.358(7) . ?
C48 H48 0.9500 . ?
C49 C50 1.406(8) . ?
C49 H49 0.9500 . ?
C50 C51 1.375(7) . ?
C50 N15 1.447(6) . ?
C51 C52 1.388(7) . ?
C51 H51 0.9500 . ?
C52 C53 1.442(7) . ?
C53 N16 1.297(6) . ?
C53 H53 0.9500 . ?
C54 N17 1.326(6) . ?
C54 N18 1.348(7) . ?
C54 S3 1.739(5) . ?
C55 N19 1.355(7) . ?
C55 C56 1.395(8) . ?
C55 H55 0.9500 . ?
C56 C57 1.373(8) . ?
C56 H56 0.9500 . ?
C57 C58 1.370(8) . ?
C57 H57 0.9500 . ?
C58 C59 1.380(8) . ?
C58 H58 0.9500 . ?
C59 N19 1.345(7) . ?
C59 C60 1.496(7) . ?
C60 N20 1.321(7) . ?
C60 C61 1.394(8) . ?
C61 C62 1.387(9) . ?
C61 H61 0.9500 . ?
C62 C63 1.386(9) . ?
C62 H62 0.9500 . ?
C63 C64 1.369(8) . ?
C63 H63 0.9500 . ?
C64 N20 1.357(7) . ?
C64 H64 0.9500 . ?
C65 O10 1.294(6) . ?
C65 C66 1.422(8) . ?
C65 C70 1.437(8) . ?
C66 C67 1.370(8) . ?
C66 H66 0.9500 . ?
C67 C68 1.421(8) . ?
C67 H67 0.9500 . ?
C68 C69 1.372(7) . ?
C68 N21 1.436(7) . ?
C69 C70 1.401(7) . ?
C69 H69 0.9500 . ?
C70 C71 1.439(7) . ?
C71 N22 1.295(6) . ?
C71 H71 0.9500 . ?
C72 N23 1.326(6) . ?
C72 N24 1.351(7) . ?
C72 S4 1.735(5) . ?
C73 O13 1.362(9) . ?
C73 H73A 0.9800 . ?
C73 H73B 0.9800 . ?
C73 H73C 0.9800 . ?
C74 O14 1.374(9) . ?
C74 H74A 0.9800 . ?
C74 H74B 0.9800 . ?
C74 H74C 0.9800 . ?
C75 O15 1.260(10) . ?
C75 H75A 0.9800 . ?
C75 H75B 0.9800 . ?
C75 H75C 0.9800 . ?
N1 Cu1 2.250(5) . ?
N2 Cu1 2.012(4) . ?
N3 O3 1.228(6) . ?
N3 O2 1.237(6) . ?
N4 N5 1.398(6) . ?
N4 Cu1 1.953(4) . ?
N6 H6A 0.86(2) . ?
N6 H6B 0.89(5) . ?
N7 Cu2 2.024(4) . ?
N8 Cu2 2.245(4) . ?
N9 O6 1.230(6) . ?
N9 O5 1.239(6) . ?
N10 N11 1.390(6) . ?
N10 Cu2 1.952(4) . ?
N12 H12A 0.63(6) . ?
N12 H12B 0.83(6) . ?
N13 Cu3 2.251(5) . ?
N14 Cu3 2.011(4) . ?
N15 O8 1.230(6) . ?
N15 O9 1.247(6) . ?
N16 N17 1.396(6) . ?
N16 Cu3 1.958(4) . ?
N18 H18A 0.82(6) . ?
N18 H18B 0.93(6) . ?
N19 Cu4 2.030(4) . ?
N20 Cu4 2.221(4) . ?
N21 O12 1.225(6) . ?
N21 O11 1.234(6) . ?
N22 N23 1.393(6) . ?
N22 Cu4 1.969(4) . ?
N24 H24A 0.76(6) . ?
N24 H24B 0.85(6) . ?
O1 Cu1 1.974(4) . ?
O4 Cu2 1.953(3) . ?
O7 Cu3 1.967(3) . ?
O10 Cu4 1.950(4) . ?
O13 H13A 0.8400 . ?
O14 H14 0.8400 . ?
O15 H15A 0.8400 . ?
S1 Cu1 2.2510(14) . ?
S2 Cu2 2.2599(14) . ?
S3 Cu3 2.2507(14) . ?
S4 Cu4 2.2653(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.7(6) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 118.8(7) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 118.5(6) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 119.9(6) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 121.3(6) . . ?
N1 C5 C6 115.2(5) . . ?
C4 C5 C6 123.4(6) . . ?
N2 C6 C7 121.8(6) . . ?
N2 C6 C5 115.4(5) . . ?
C7 C6 C5 122.7(5) . . ?
C6 C7 C8 118.6(6) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C9 C8 C7 120.4(6) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 117.8(6) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
N2 C10 C9 123.4(6) . . ?
N2 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
O1 C11 C12 118.5(5) . . ?
O1 C11 C16 123.6(5) . . ?
C12 C11 C16 117.9(4) . . ?
C13 C12 C11 121.8(5) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C14 C13 C12 118.5(5) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C15 C14 C13 122.2(5) . . ?
C15 C14 N3 118.6(5) . . ?
C13 C14 N3 119.1(5) . . ?
C14 C15 C16 119.9(5) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 119.0(5) . . ?
C15 C16 C17 117.1(5) . . ?
C11 C16 C17 123.9(4) . . ?
N4 C17 C16 124.9(5) . . ?
N4 C17 H17 117.6 . . ?
C16 C17 H17 117.6 . . ?
N5 C18 N6 116.8(5) . . ?
N5 C18 S1 126.0(4) . . ?
N6 C18 S1 117.2(4) . . ?
N7 C19 C20 122.8(5) . . ?
N7 C19 H19 118.6 . . ?
C20 C19 H19 118.6 . . ?
C19 C20 C21 118.0(6) . . ?
C19 C20 H20 121.0 . . ?
C21 C20 H20 121.0 . . ?
C22 C21 C20 120.1(6) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 119.4(6) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
N7 C23 C22 120.5(5) . . ?
N7 C23 C24 116.1(5) . . ?
C22 C23 C24 123.3(5) . . ?
N8 C24 C25 120.3(5) . . ?
N8 C24 C23 115.4(5) . . ?
C25 C24 C23 124.3(5) . . ?
C26 C25 C24 120.4(6) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C27 C26 C25 118.7(6) . . ?
C27 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C26 C27 C28 118.4(6) . . ?
C26 C27 H27 120.8 . . ?
C28 C27 H27 120.8 . . ?
N8 C28 C27 122.9(6) . . ?
N8 C28 H28 118.6 . . ?
C27 C28 H28 118.6 . . ?
O4 C29 C30 119.7(5) . . ?
O4 C29 C34 123.0(5) . . ?
C30 C29 C34 117.3(5) . . ?
C31 C30 C29 123.0(5) . . ?
C31 C30 H30 118.5 . . ?
C29 C30 H30 118.5 . . ?
C30 C31 C32 118.3(5) . . ?
C30 C31 H31 120.9 . . ?
C32 C31 H31 120.9 . . ?
C33 C32 C31 122.2(5) . . ?
C33 C32 N9 119.2(5) . . ?
C31 C32 N9 118.6(5) . . ?
C32 C33 C34 119.8(5) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C33 C34 C35 116.9(5) . . ?
C33 C34 C29 119.2(5) . . ?
C35 C34 C29 123.7(4) . . ?
N10 C35 C34 125.1(5) . . ?
N10 C35 H35 117.5 . . ?
C34 C35 H35 117.5 . . ?
N11 C36 N12 118.6(5) . . ?
N11 C36 S2 124.3(4) . . ?
N12 C36 S2 117.1(4) . . ?
N13 C37 C38 122.6(6) . . ?
N13 C37 H37 118.7 . . ?
C38 C37 H37 118.7 . . ?
C37 C38 C39 119.6(6) . . ?
C37 C38 H38 120.2 . . ?
C39 C38 H38 120.2 . . ?
C40 C39 C38 118.8(6) . . ?
C40 C39 H39 120.6 . . ?
C38 C39 H39 120.6 . . ?
C39 C40 C41 118.9(6) . . ?
C39 C40 H40 120.6 . . ?
C41 C40 H40 120.6 . . ?
N13 C41 C40 121.0(6) . . ?
N13 C41 C42 116.3(5) . . ?
C40 C41 C42 122.7(5) . . ?
N14 C42 C43 119.8(5) . . ?
N14 C42 C41 116.1(5) . . ?
C43 C42 C41 124.1(5) . . ?
C42 C43 C44 119.5(6) . . ?
C42 C43 H43 120.3 . . ?
C44 C43 H43 120.3 . . ?
C45 C44 C43 120.0(6) . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C46 118.5(6) . . ?
C44 C45 H45 120.7 . . ?
C46 C45 H45 120.7 . . ?
N14 C46 C45 122.6(6) . . ?
N14 C46 H46 118.7 . . ?
C45 C46 H46 118.7 . . ?
O7 C47 C48 118.2(5) . . ?
O7 C47 C52 124.0(5) . . ?
C48 C47 C52 117.8(5) . . ?
C49 C48 C47 122.0(5) . . ?
C49 C48 H48 119.0 . . ?
C47 C48 H48 119.0 . . ?
C48 C49 C50 118.7(5) . . ?
C48 C49 H49 120.6 . . ?
C50 C49 H49 120.6 . . ?
C51 C50 C49 121.4(5) . . ?
C51 C50 N15 120.3(5) . . ?
C49 C50 N15 118.2(5) . . ?
C50 C51 C52 121.3(5) . . ?
C50 C51 H51 119.4 . . ?
C52 C51 H51 119.4 . . ?
C51 C52 C47 118.7(5) . . ?
C51 C52 C53 117.4(5) . . ?
C47 C52 C53 123.8(5) . . ?
N16 C53 C52 125.4(5) . . ?
N16 C53 H53 117.3 . . ?
C52 C53 H53 117.3 . . ?
N17 C54 N18 117.6(5) . . ?
N17 C54 S3 125.2(4) . . ?
N18 C54 S3 117.2(4) . . ?
N19 C55 C56 121.9(5) . . ?
N19 C55 H55 119.1 . . ?
C56 C55 H55 119.1 . . ?
C57 C56 C55 118.6(5) . . ?
C57 C56 H56 120.7 . . ?
C55 C56 H56 120.7 . . ?
C58 C57 C56 119.4(6) . . ?
C58 C57 H57 120.3 . . ?
C56 C57 H57 120.3 . . ?
C57 C58 C59 120.2(6) . . ?
C57 C58 H58 119.9 . . ?
C59 C58 H58 119.9 . . ?
N19 C59 C58 121.2(5) . . ?
N19 C59 C60 115.1(5) . . ?
C58 C59 C60 123.6(5) . . ?
N20 C60 C61 123.0(5) . . ?
N20 C60 C59 115.5(5) . . ?
C61 C60 C59 121.5(5) . . ?
C62 C61 C60 117.7(6) . . ?
C62 C61 H61 121.1 . . ?
C60 C61 H61 121.1 . . ?
C63 C62 C61 119.6(6) . . ?
C63 C62 H62 120.2 . . ?
C61 C62 H62 120.2 . . ?
C64 C63 C62 118.8(6) . . ?
C64 C63 H63 120.6 . . ?
C62 C63 H63 120.6 . . ?
N20 C64 C63 122.2(6) . . ?
N20 C64 H64 118.9 . . ?
C63 C64 H64 118.9 . . ?
O10 C65 C66 119.1(5) . . ?
O10 C65 C70 123.5(5) . . ?
C66 C65 C70 117.4(5) . . ?
C67 C66 C65 122.4(6) . . ?
C67 C66 H66 118.8 . . ?
C65 C66 H66 118.8 . . ?
C66 C67 C68 119.3(5) . . ?
C66 C67 H67 120.4 . . ?
C68 C67 H67 120.4 . . ?
C69 C68 C67 119.8(5) . . ?
C69 C68 N21 120.3(5) . . ?
C67 C68 N21 119.9(5) . . ?
C68 C69 C70 121.9(5) . . ?
C68 C69 H69 119.0 . . ?
C70 C69 H69 119.0 . . ?
C69 C70 C65 119.1(5) . . ?
C69 C70 C71 116.9(5) . . ?
C65 C70 C71 123.9(5) . . ?
N22 C71 C70 125.3(5) . . ?
N22 C71 H71 117.4 . . ?
C70 C71 H71 117.4 . . ?
N23 C72 N24 117.0(5) . . ?
N23 C72 S4 125.7(4) . . ?
N24 C72 S4 117.3(4) . . ?
O13 C73 H73A 109.5 . . ?
O13 C73 H73B 109.5 . . ?
H73A C73 H73B 109.5 . . ?
O13 C73 H73C 109.5 . . ?
H73A C73 H73C 109.5 . . ?
H73B C73 H73C 109.5 . . ?
O14 C74 H74A 109.5 . . ?
O14 C74 H74B 109.5 . . ?
H74A C74 H74B 109.5 . . ?
O14 C74 H74C 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
O15 C75 H75A 109.5 . . ?
O15 C75 H75B 109.5 . . ?
H75A C75 H75B 109.5 . . ?
O15 C75 H75C 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 109.5 . . ?
C5 N1 C1 119.6(5) . . ?
C5 N1 Cu1 112.2(4) . . ?
C1 N1 Cu1 128.0(4) . . ?
C10 N2 C6 118.0(5) . . ?
C10 N2 Cu1 122.3(4) . . ?
C6 N2 Cu1 119.2(4) . . ?
O3 N3 O2 121.9(4) . . ?
O3 N3 C14 120.2(5) . . ?
O2 N3 C14 117.8(5) . . ?
C17 N4 N5 115.6(4) . . ?
C17 N4 Cu1 124.2(4) . . ?
N5 N4 Cu1 119.6(3) . . ?
C18 N5 N4 112.2(4) . . ?
C18 N6 H6A 117(4) . . ?
C18 N6 H6B 111(4) . . ?
H6A N6 H6B 132(5) . . ?
C19 N7 C23 119.1(5) . . ?
C19 N7 Cu2 121.7(4) . . ?
C23 N7 Cu2 119.0(3) . . ?
C24 N8 C28 119.3(5) . . ?
C24 N8 Cu2 111.9(3) . . ?
C28 N8 Cu2 127.8(4) . . ?
O6 N9 O5 122.2(4) . . ?
O6 N9 C32 119.9(4) . . ?
O5 N9 C32 117.8(5) . . ?
C35 N10 N11 115.2(4) . . ?
C35 N10 Cu2 123.7(4) . . ?
N11 N10 Cu2 120.8(3) . . ?
C36 N11 N10 113.9(4) . . ?
C36 N12 H12A 115(7) . . ?
C36 N12 H12B 118(4) . . ?
H12A N12 H12B 127(8) . . ?
C37 N13 C41 119.1(5) . . ?
C37 N13 Cu3 129.7(4) . . ?
C41 N13 Cu3 111.2(4) . . ?
C46 N14 C42 119.5(5) . . ?
C46 N14 Cu3 121.2(4) . . ?
C42 N14 Cu3 119.0(4) . . ?
O8 N15 O9 122.0(5) . . ?
O8 N15 C50 119.1(5) . . ?
O9 N15 C50 118.9(5) . . ?
C53 N16 N17 115.4(4) . . ?
C53 N16 Cu3 125.1(4) . . ?
N17 N16 Cu3 119.1(3) . . ?
C54 N17 N16 112.9(4) . . ?
C54 N18 H18A 115(4) . . ?
C54 N18 H18B 112(4) . . ?
H18A N18 H18B 130(6) . . ?
C59 N19 C55 118.7(5) . . ?
C59 N19 Cu4 118.7(4) . . ?
C55 N19 Cu4 122.4(4) . . ?
C60 N20 C64 118.6(5) . . ?
C60 N20 Cu4 112.6(4) . . ?
C64 N20 Cu4 128.1(4) . . ?
O12 N21 O11 122.3(5) . . ?
O12 N21 C68 119.1(5) . . ?
O11 N21 C68 118.6(5) . . ?
C71 N22 N23 115.3(5) . . ?
C71 N22 Cu4 124.5(4) . . ?
N23 N22 Cu4 119.9(3) . . ?
C72 N23 N22 113.3(4) . . ?
C72 N24 H24A 115(5) . . ?
C72 N24 H24B 117(4) . . ?
H24A N24 H24B 123(6) . . ?
C11 O1 Cu1 124.8(3) . . ?
C29 O4 Cu2 125.0(3) . . ?
C47 O7 Cu3 127.0(3) . . ?
C65 O10 Cu4 126.9(4) . . ?
C73 O13 H13A 109.5 . . ?
C74 O14 H14 109.5 . . ?
C75 O15 H15A 109.5 . . ?
C18 S1 Cu1 93.62(17) . . ?
C36 S2 Cu2 94.68(17) . . ?
C54 S3 Cu3 93.58(17) . . ?
C72 S4 Cu4 94.11(16) . . ?
N4 Cu1 O1 92.45(16) . . ?
N4 Cu1 N2 171.11(18) . . ?
O1 Cu1 N2 92.31(16) . . ?
N4 Cu1 N1 94.65(17) . . ?
O1 Cu1 N1 101.23(16) . . ?
N2 Cu1 N1 77.05(18) . . ?
N4 Cu1 S1 86.23(12) . . ?
O1 Cu1 S1 150.20(11) . . ?
N2 Cu1 S1 93.34(13) . . ?
N1 Cu1 S1 108.55(13) . . ?
N10 Cu2 O4 92.84(16) . . ?
N10 Cu2 N7 174.84(17) . . ?
O4 Cu2 N7 87.80(16) . . ?
N10 Cu2 N8 98.41(17) . . ?
O4 Cu2 N8 98.64(17) . . ?
N7 Cu2 N8 76.44(17) . . ?
N10 Cu2 S2 85.76(12) . . ?
O4 Cu2 S2 155.48(12) . . ?
N7 Cu2 S2 95.77(12) . . ?
N8 Cu2 S2 105.79(13) . . ?
N16 Cu3 O7 92.83(16) . . ?
N16 Cu3 N14 176.12(17) . . ?
O7 Cu3 N14 90.85(16) . . ?
N16 Cu3 N13 101.01(17) . . ?
O7 Cu3 N13 97.48(16) . . ?
N14 Cu3 N13 77.27(18) . . ?
N16 Cu3 S3 85.81(12) . . ?
O7 Cu3 S3 154.37(13) . . ?
N14 Cu3 S3 91.40(13) . . ?
N13 Cu3 S3 107.92(12) . . ?
O10 Cu4 N22 92.44(16) . . ?
O10 Cu4 N19 90.60(16) . . ?
N22 Cu4 N19 175.66(18) . . ?
O10 Cu4 N20 95.90(16) . . ?
N22 Cu4 N20 99.69(17) . . ?
N19 Cu4 N20 76.90(17) . . ?
O10 Cu4 S4 156.89(12) . . ?
N22 Cu4 S4 85.88(12) . . ?
N19 Cu4 S4 92.53(13) . . ?
N20 Cu4 S4 107.11(12) . . ?

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
N1 C1 C2 C3 1.8(11) . . . . ?
C1 C2 C3 C4 -3.8(12) . . . . ?
C2 C3 C4 C5 2.0(11) . . . . ?
C3 C4 C5 N1 2.0(10) . . . . ?
C3 C4 C5 C6 -175.8(6) . . . . ?
N1 C5 C6 N2 9.6(8) . . . . ?
C4 C5 C6 N2 -172.6(6) . . . . ?
N1 C5 C6 C7 -166.0(6) . . . . ?
C4 C5 C6 C7 11.8(10) . . . . ?
N2 C6 C7 C8 1.4(10) . . . . ?
C5 C6 C7 C8 176.7(6) . . . . ?
C6 C7 C8 C9 -2.7(12) . . . . ?
C7 C8 C9 C10 2.0(11) . . . . ?
C8 C9 C10 N2 0.1(10) . . . . ?
O1 C11 C12 C13 -172.6(5) . . . . ?
C16 C11 C12 C13 6.4(8) . . . . ?
C11 C12 C13 C14 -0.9(8) . . . . ?
C12 C13 C14 C15 -5.3(8) . . . . ?
C12 C13 C14 N3 176.2(5) . . . . ?
C13 C14 C15 C16 5.5(8) . . . . ?
N3 C14 C15 C16 -175.9(5) . . . . ?
C14 C15 C16 C11 0.3(8) . . . . ?
C14 C15 C16 C17 -177.8(5) . . . . ?
O1 C11 C16 C15 172.9(5) . . . . ?
C12 C11 C16 C15 -6.1(7) . . . . ?
O1 C11 C16 C17 -9.1(8) . . . . ?
C12 C11 C16 C17 171.9(5) . . . . ?
C15 C16 C17 N4 -173.4(5) . . . . ?
C11 C16 C17 N4 8.6(8) . . . . ?
N7 C19 C20 C21 0.8(9) . . . . ?
C19 C20 C21 C22 0.1(9) . . . . ?
C20 C21 C22 C23 -1.1(9) . . . . ?
C21 C22 C23 N7 1.4(8) . . . . ?
C21 C22 C23 C24 178.0(5) . . . . ?
N7 C23 C24 N8 10.3(7) . . . . ?
C22 C23 C24 N8 -166.5(5) . . . . ?
N7 C23 C24 C25 -167.7(5) . . . . ?
C22 C23 C24 C25 15.5(8) . . . . ?
N8 C24 C25 C26 3.8(9) . . . . ?
C23 C24 C25 C26 -178.3(5) . . . . ?
C24 C25 C26 C27 -2.2(9) . . . . ?
C25 C26 C27 C28 0.3(9) . . . . ?
C26 C27 C28 N8 0.0(9) . . . . ?
O4 C29 C30 C31 176.8(5) . . . . ?
C34 C29 C30 C31 -3.8(8) . . . . ?
C29 C30 C31 C32 1.1(8) . . . . ?
C30 C31 C32 C33 2.6(8) . . . . ?
C30 C31 C32 N9 -179.3(5) . . . . ?
C31 C32 C33 C34 -3.3(8) . . . . ?
N9 C32 C33 C34 178.6(4) . . . . ?
C32 C33 C34 C35 175.2(4) . . . . ?
C32 C33 C34 C29 0.3(7) . . . . ?
O4 C29 C34 C33 -177.6(5) . . . . ?
C30 C29 C34 C33 3.0(7) . . . . ?
O4 C29 C34 C35 7.9(8) . . . . ?
C30 C29 C34 C35 -171.5(5) . . . . ?
C33 C34 C35 N10 174.6(5) . . . . ?
C29 C34 C35 N10 -10.8(8) . . . . ?
N13 C37 C38 C39 1.3(10) . . . . ?
C37 C38 C39 C40 -1.0(11) . . . . ?
C38 C39 C40 C41 -0.6(11) . . . . ?
C39 C40 C41 N13 2.1(10) . . . . ?
C39 C40 C41 C42 -177.6(6) . . . . ?
N13 C41 C42 N14 3.4(7) . . . . ?
C40 C41 C42 N14 -176.8(6) . . . . ?
N13 C41 C42 C43 -174.6(5) . . . . ?
C40 C41 C42 C43 5.1(9) . . . . ?
N14 C42 C43 C44 0.5(9) . . . . ?
C41 C42 C43 C44 178.5(5) . . . . ?
C42 C43 C44 C45 -1.0(9) . . . . ?
C43 C44 C45 C46 0.4(9) . . . . ?
C44 C45 C46 N14 0.9(9) . . . . ?
O7 C47 C48 C49 -179.2(5) . . . . ?
C52 C47 C48 C49 0.1(8) . . . . ?
C47 C48 C49 C50 0.8(9) . . . . ?
C48 C49 C50 C51 -1.1(8) . . . . ?
C48 C49 C50 N15 -179.2(5) . . . . ?
C49 C50 C51 C52 0.4(8) . . . . ?
N15 C50 C51 C52 178.4(5) . . . . ?
C50 C51 C52 C47 0.6(8) . . . . ?
C50 C51 C52 C53 -177.5(5) . . . . ?
O7 C47 C52 C51 178.4(5) . . . . ?
C48 C47 C52 C51 -0.8(7) . . . . ?
O7 C47 C52 C53 -3.6(8) . . . . ?
C48 C47 C52 C53 177.1(5) . . . . ?
C51 C52 C53 N16 176.4(5) . . . . ?
C47 C52 C53 N16 -1.6(8) . . . . ?
N19 C55 C56 C57 -0.1(9) . . . . ?
C55 C56 C57 C58 0.5(9) . . . . ?
C56 C57 C58 C59 0.6(9) . . . . ?
C57 C58 C59 N19 -2.2(9) . . . . ?
C57 C58 C59 C60 -179.3(5) . . . . ?
N19 C59 C60 N20 -11.1(7) . . . . ?
C58 C59 C60 N20 166.1(5) . . . . ?
N19 C59 C60 C61 170.0(5) . . . . ?
C58 C59 C60 C61 -12.8(9) . . . . ?
N20 C60 C61 C62 -1.1(10) . . . . ?
C59 C60 C61 C62 177.7(6) . . . . ?
C60 C61 C62 C63 -0.4(10) . . . . ?
C61 C62 C63 C64 1.2(10) . . . . ?
C62 C63 C64 N20 -0.6(9) . . . . ?
O10 C65 C66 C67 178.0(5) . . . . ?
C70 C65 C66 C67 -2.3(8) . . . . ?
C65 C66 C67 C68 -0.3(9) . . . . ?
C66 C67 C68 C69 2.0(9) . . . . ?
C66 C67 C68 N21 -179.3(5) . . . . ?
C67 C68 C69 C70 -1.1(9) . . . . ?
N21 C68 C69 C70 -179.8(5) . . . . ?
C68 C69 C70 C65 -1.4(8) . . . . ?
C68 C69 C70 C71 175.7(5) . . . . ?
O10 C65 C70 C69 -177.2(5) . . . . ?
C66 C65 C70 C69 3.1(7) . . . . ?
O10 C65 C70 C71 5.8(8) . . . . ?
C66 C65 C70 C71 -173.9(5) . . . . ?
C69 C70 C71 N22 178.9(5) . . . . ?
C65 C70 C71 N22 -4.1(9) . . . . ?
C4 C5 N1 C1 -4.1(9) . . . . ?
C6 C5 N1 C1 173.9(5) . . . . ?
C4 C5 N1 Cu1 171.3(5) . . . . ?
C6 C5 N1 Cu1 -10.7(6) . . . . ?
C2 C1 N1 C5 2.2(9) . . . . ?
C2 C1 N1 Cu1 -172.4(5) . . . . ?
C9 C10 N2 C6 -1.4(9) . . . . ?
C9 C10 N2 Cu1 -173.3(5) . . . . ?
C7 C6 N2 C10 0.6(9) . . . . ?
C5 C6 N2 C10 -175.0(5) . . . . ?
C7 C6 N2 Cu1 172.8(5) . . . . ?
C5 C6 N2 Cu1 -2.9(7) . . . . ?
C15 C14 N3 O3 3.7(7) . . . . ?
C13 C14 N3 O3 -177.8(5) . . . . ?
C15 C14 N3 O2 -179.2(5) . . . . ?
C13 C14 N3 O2 -0.6(7) . . . . ?
C16 C17 N4 N5 -176.6(4) . . . . ?
C16 C17 N4 Cu1 12.6(7) . . . . ?
N6 C18 N5 N4 -179.7(4) . . . . ?
S1 C18 N5 N4 2.5(7) . . . . ?
C17 N4 N5 C18 174.7(4) . . . . ?
Cu1 N4 N5 C18 -14.1(5) . . . . ?
C20 C19 N7 C23 -0.5(8) . . . . ?
C20 C19 N7 Cu2 -175.6(4) . . . . ?
C22 C23 N7 C19 -0.5(7) . . . . ?
C24 C23 N7 C19 -177.4(4) . . . . ?
C22 C23 N7 Cu2 174.7(4) . . . . ?
C24 C23 N7 Cu2 -2.2(6) . . . . ?
C25 C24 N8 C28 -3.4(8) . . . . ?
C23 C24 N8 C28 178.5(5) . . . . ?
C25 C24 N8 Cu2 165.8(4) . . . . ?
C23 C24 N8 Cu2 -12.4(5) . . . . ?
C27 C28 N8 C24 1.6(9) . . . . ?
C27 C28 N8 Cu2 -165.7(5) . . . . ?
C33 C32 N9 O6 -0.8(7) . . . . ?
C31 C32 N9 O6 -179.0(5) . . . . ?
C33 C32 N9 O5 -178.5(5) . . . . ?
C31 C32 N9 O5 3.3(7) . . . . ?
C34 C35 N10 N11 176.2(4) . . . . ?
C34 C35 N10 Cu2 -9.9(7) . . . . ?
N12 C36 N11 N10 179.8(5) . . . . ?
S2 C36 N11 N10 -0.8(6) . . . . ?
C35 N10 N11 C36 -179.1(4) . . . . ?
Cu2 N10 N11 C36 6.8(6) . . . . ?
C38 C37 N13 C41 0.1(8) . . . . ?
C38 C37 N13 Cu3 179.8(5) . . . . ?
C40 C41 N13 C37 -1.8(8) . . . . ?
C42 C41 N13 C37 177.9(5) . . . . ?
C40 C41 N13 Cu3 178.5(5) . . . . ?
C42 C41 N13 Cu3 -1.8(6) . . . . ?
C45 C46 N14 C42 -1.5(8) . . . . ?
C45 C46 N14 Cu3 -175.3(4) . . . . ?
C43 C42 N14 C46 0.8(8) . . . . ?
C41 C42 N14 C46 -177.4(5) . . . . ?
C43 C42 N14 Cu3 174.7(4) . . . . ?
C41 C42 N14 Cu3 -3.4(6) . . . . ?
C51 C50 N15 O8 177.6(5) . . . . ?
C49 C50 N15 O8 -4.3(8) . . . . ?
C51 C50 N15 O9 -3.0(8) . . . . ?
C49 C50 N15 O9 175.1(5) . . . . ?
C52 C53 N16 N17 -174.3(5) . . . . ?
C52 C53 N16 Cu3 12.9(8) . . . . ?
N18 C54 N17 N16 -179.6(4) . . . . ?
S3 C54 N17 N16 -0.2(7) . . . . ?
C53 N16 N17 C54 171.6(5) . . . . ?
Cu3 N16 N17 C54 -15.1(6) . . . . ?
C58 C59 N19 C55 2.6(8) . . . . ?
C60 C59 N19 C55 179.9(5) . . . . ?
C58 C59 N19 Cu4 -172.6(4) . . . . ?
C60 C59 N19 Cu4 4.7(6) . . . . ?
C56 C55 N19 C59 -1.5(8) . . . . ?
C56 C55 N19 Cu4 173.5(4) . . . . ?
C61 C60 N20 C64 1.7(8) . . . . ?
C59 C60 N20 C64 -177.2(5) . . . . ?
C61 C60 N20 Cu4 -169.7(5) . . . . ?
C59 C60 N20 Cu4 11.4(6) . . . . ?
C63 C64 N20 C60 -0.8(8) . . . . ?
C63 C64 N20 Cu4 169.1(4) . . . . ?
C69 C68 N21 O12 4.7(8) . . . . ?
C67 C68 N21 O12 -174.0(5) . . . . ?
C69 C68 N21 O11 -175.5(5) . . . . ?
C67 C68 N21 O11 5.9(8) . . . . ?
C70 C71 N22 N23 174.6(5) . . . . ?
C70 C71 N22 Cu4 -11.6(8) . . . . ?
N24 C72 N23 N22 174.2(4) . . . . ?
S4 C72 N23 N22 -2.5(7) . . . . ?
C71 N22 N23 C72 -175.5(5) . . . . ?
Cu4 N22 N23 C72 10.4(6) . . . . ?
C12 C11 O1 Cu1 167.4(4) . . . . ?
C16 C11 O1 Cu1 -11.6(7) . . . . ?
C30 C29 O4 Cu2 -165.5(4) . . . . ?
C34 C29 O4 Cu2 15.2(7) . . . . ?
C48 C47 O7 Cu3 175.8(4) . . . . ?
C52 C47 O7 Cu3 -3.5(8) . . . . ?
C66 C65 O10 Cu4 -171.5(4) . . . . ?
C70 C65 O10 Cu4 8.8(7) . . . . ?
N5 C18 S1 Cu1 7.4(5) . . . . ?
N6 C18 S1 Cu1 -170.4(4) . . . . ?
N11 C36 S2 Cu2 -4.0(5) . . . . ?
N12 C36 S2 Cu2 175.4(4) . . . . ?
N17 C54 S3 Cu3 11.7(5) . . . . ?
N18 C54 S3 Cu3 -168.9(4) . . . . ?
N23 C72 S4 Cu4 -4.6(5) . . . . ?
N24 C72 S4 Cu4 178.6(4) . . . . ?
C17 N4 Cu1 O1 -23.9(4) . . . . ?
N5 N4 Cu1 O1 165.7(3) . . . . ?
C17 N4 Cu1 N1 77.6(4) . . . . ?
N5 N4 Cu1 N1 -92.9(4) . . . . ?
C17 N4 Cu1 S1 -174.1(4) . . . . ?
N5 N4 Cu1 S1 15.5(3) . . . . ?
C11 O1 Cu1 N4 23.6(4) . . . . ?
C11 O1 Cu1 N2 -148.9(4) . . . . ?
C11 O1 Cu1 N1 -71.6(4) . . . . ?
C11 O1 Cu1 S1 110.3(4) . . . . ?
C10 N2 Cu1 O1 -89.3(4) . . . . ?
C6 N2 Cu1 O1 98.9(4) . . . . ?
C10 N2 Cu1 N1 169.7(5) . . . . ?
C6 N2 Cu1 N1 -2.1(4) . . . . ?
C10 N2 Cu1 S1 61.4(4) . . . . ?
C6 N2 Cu1 S1 -110.3(4) . . . . ?
C5 N1 Cu1 N4 -176.0(4) . . . . ?
C1 N1 Cu1 N4 -1.1(5) . . . . ?
C5 N1 Cu1 O1 -82.5(4) . . . . ?
C1 N1 Cu1 O1 92.4(5) . . . . ?
C5 N1 Cu1 N2 7.3(4) . . . . ?
C1 N1 Cu1 N2 -177.8(5) . . . . ?
C5 N1 Cu1 S1 96.5(4) . . . . ?
C1 N1 Cu1 S1 -88.6(5) . . . . ?
C18 S1 Cu1 N4 -10.3(2) . . . . ?
C18 S1 Cu1 O1 -98.7(3) . . . . ?
C18 S1 Cu1 N2 160.8(2) . . . . ?
C18 S1 Cu1 N1 83.3(2) . . . . ?
C35 N10 Cu2 O4 23.4(4) . . . . ?
N11 N10 Cu2 O4 -163.0(4) . . . . ?
C35 N10 Cu2 N8 -75.8(4) . . . . ?
N11 N10 Cu2 N8 97.8(4) . . . . ?
C35 N10 Cu2 S2 178.8(4) . . . . ?
N11 N10 Cu2 S2 -7.6(3) . . . . ?
C29 O4 Cu2 N10 -26.4(4) . . . . ?
C29 O4 Cu2 N7 148.5(4) . . . . ?
C29 O4 Cu2 N8 72.6(4) . . . . ?
C29 O4 Cu2 S2 -112.4(4) . . . . ?
C19 N7 Cu2 O4 72.3(4) . . . . ?
C23 N7 Cu2 O4 -102.7(4) . . . . ?
C19 N7 Cu2 N8 171.8(4) . . . . ?
C23 N7 Cu2 N8 -3.3(4) . . . . ?
C19 N7 Cu2 S2 -83.3(4) . . . . ?
C23 N7 Cu2 S2 101.6(4) . . . . ?
C24 N8 Cu2 N10 -171.5(4) . . . . ?
C28 N8 Cu2 N10 -3.5(5) . . . . ?
C24 N8 Cu2 O4 94.3(4) . . . . ?
C28 N8 Cu2 O4 -97.7(5) . . . . ?
C24 N8 Cu2 N7 8.7(4) . . . . ?
C28 N8 Cu2 N7 176.7(5) . . . . ?
C24 N8 Cu2 S2 -83.6(4) . . . . ?
C28 N8 Cu2 S2 84.4(5) . . . . ?
C36 S2 Cu2 N10 5.2(2) . . . . ?
C36 S2 Cu2 O4 92.8(3) . . . . ?
C36 S2 Cu2 N7 -169.9(2) . . . . ?
C36 S2 Cu2 N8 -92.3(2) . . . . ?
C53 N16 Cu3 O7 -14.7(4) . . . . ?
N17 N16 Cu3 O7 172.7(4) . . . . ?
C53 N16 Cu3 N13 83.4(4) . . . . ?
N17 N16 Cu3 N13 -89.1(4) . . . . ?
C53 N16 Cu3 S3 -169.1(4) . . . . ?
N17 N16 Cu3 S3 18.3(3) . . . . ?
C47 O7 Cu3 N16 10.3(4) . . . . ?
C47 O7 Cu3 N14 -168.4(4) . . . . ?
C47 O7 Cu3 N13 -91.2(4) . . . . ?
C47 O7 Cu3 S3 96.5(5) . . . . ?
C46 N14 Cu3 O7 -86.8(4) . . . . ?
C42 N14 Cu3 O7 99.3(4) . . . . ?
C46 N14 Cu3 N13 175.7(4) . . . . ?
C42 N14 Cu3 N13 1.9(4) . . . . ?
C46 N14 Cu3 S3 67.6(4) . . . . ?
C42 N14 Cu3 S3 -106.2(4) . . . . ?
C37 N13 Cu3 N16 -3.1(5) . . . . ?
C41 N13 Cu3 N16 176.5(4) . . . . ?
C37 N13 Cu3 O7 91.2(5) . . . . ?
C41 N13 Cu3 O7 -89.1(4) . . . . ?
C37 N13 Cu3 N14 -179.6(5) . . . . ?
C41 N13 Cu3 N14 0.1(4) . . . . ?
C37 N13 Cu3 S3 -92.3(5) . . . . ?
C41 N13 Cu3 S3 87.4(4) . . . . ?
C54 S3 Cu3 N16 -13.5(2) . . . . ?
C54 S3 Cu3 O7 -101.3(3) . . . . ?
C54 S3 Cu3 N14 163.8(2) . . . . ?
C54 S3 Cu3 N13 86.8(2) . . . . ?
C65 O10 Cu4 N22 -17.6(4) . . . . ?
C65 O10 Cu4 N19 159.3(4) . . . . ?
C65 O10 Cu4 N20 82.4(4) . . . . ?
C65 O10 Cu4 S4 -102.8(5) . . . . ?
C71 N22 Cu4 O10 18.7(5) . . . . ?
N23 N22 Cu4 O10 -167.8(4) . . . . ?
C71 N22 Cu4 N20 -77.8(5) . . . . ?
N23 N22 Cu4 N20 95.8(4) . . . . ?
C71 N22 Cu4 S4 175.6(4) . . . . ?
N23 N22 Cu4 S4 -10.9(3) . . . . ?
C59 N19 Cu4 O10 -95.0(4) . . . . ?
C55 N19 Cu4 O10 90.0(4) . . . . ?
C59 N19 Cu4 N20 0.9(4) . . . . ?
C55 N19 Cu4 N20 -174.1(4) . . . . ?
C59 N19 Cu4 S4 107.9(4) . . . . ?
C55 N19 Cu4 S4 -67.1(4) . . . . ?
C60 N20 Cu4 O10 82.2(4) . . . . ?
C64 N20 Cu4 O10 -88.2(5) . . . . ?
C60 N20 Cu4 N22 175.7(4) . . . . ?
C64 N20 Cu4 N22 5.3(5) . . . . ?
C60 N20 Cu4 N19 -7.0(4) . . . . ?
C64 N20 Cu4 N19 -177.4(5) . . . . ?
C60 N20 Cu4 S4 -95.6(4) . . . . ?
C64 N20 Cu4 S4 94.0(4) . . . . ?
C72 S4 Cu4 O10 93.5(3) . . . . ?
C72 S4 Cu4 N22 7.0(2) . . . . ?
C72 S4 Cu4 N19 -169.0(2) . . . . ?
C72 S4 Cu4 N20 -91.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.75
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.078
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.119
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1028087'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 Cu N6 O3 S'
_chemical_formula_sum            'C19 H16 Cu N6 O3 S'
_chemical_formula_weight         472.00

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.073(2)
_cell_length_b                   9.391(3)
_cell_length_c                   13.924(4)
_cell_angle_alpha                71.441(15)
_cell_angle_beta                 85.420(15)
_cell_angle_gamma                75.557(16)
_cell_volume                     969.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3975
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.97

_exptl_crystal_description       Prism
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             482
_exptl_absorpt_coefficient_mu    1.270
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6660
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12911
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_sigmaI/netI    0.1619
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         27.68
_reflns_number_total             4121
_reflns_number_gt                2632
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
There is only one restraint used during structure refinement i.e. DFIX. 
DFIX is used to fix distance of proton
 of -NH group to its N atom.  
 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1543P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4121
_refine_ls_number_parameters     275
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1888
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.3256
_refine_ls_wR_factor_gt          0.1853
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_restrained_S_all      1.239
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9184(9) 0.3186(10) 0.0706(6) 0.0533(19) Uani 1 1 d . . .
H1 H 0.8698 0.3560 0.1233 0.064 Uiso 1 1 calc R . .
C2 C 0.8658(11) 0.4011(11) -0.0262(8) 0.069(3) Uani 1 1 d . . .
H2 H 0.7830 0.4938 -0.0396 0.083 Uiso 1 1 calc R . .
C3 C 0.9358(11) 0.3460(11) -0.1015(7) 0.068(3) Uani 1 1 d . . .
H3 H 0.9007 0.4009 -0.1679 0.081 Uiso 1 1 calc R . .
C4 C 1.0605(10) 0.2073(12) -0.0821(6) 0.060(2) Uani 1 1 d . . .
H4 H 1.1086 0.1680 -0.1340 0.072 Uiso 1 1 calc R . .
C5 C 1.1099(8) 0.1304(9) 0.0181(5) 0.0431(15) Uani 1 1 d . . .
C6 C 1.2440(8) -0.0196(9) 0.0491(5) 0.0446(16) Uani 1 1 d . . .
C7 C 1.3338(11) -0.0824(11) -0.0221(6) 0.060(2) Uani 1 1 d . . .
H7 H 1.3105 -0.0366 -0.0909 0.072 Uiso 1 1 calc R . .
C8 C 1.4594(12) -0.2156(14) 0.0133(8) 0.077(3) Uani 1 1 d . . .
H8 H 1.5258 -0.2593 -0.0325 0.093 Uiso 1 1 calc R . .
C9 C 1.4876(10) -0.2841(11) 0.1142(8) 0.068(3) Uani 1 1 d . . .
H9 H 1.5710 -0.3752 0.1384 0.082 Uiso 1 1 calc R . .
C10 C 1.3881(8) -0.2140(10) 0.1799(6) 0.0501(18) Uani 1 1 d . . .
H10 H 1.4042 -0.2611 0.2493 0.060 Uiso 1 1 calc R . .
C11 C 0.8815(7) -0.1175(8) 0.3388(5) 0.0366(13) Uani 1 1 d . . .
C12 C 0.7378(7) -0.1786(9) 0.3364(5) 0.0477(17) Uani 1 1 d . . .
H12 H 0.6681 -0.1370 0.2793 0.057 Uiso 1 1 calc R . .
C13 C 0.6988(8) -0.2964(10) 0.4151(5) 0.0474(17) Uani 1 1 d . . .
H13 H 0.6060 -0.3364 0.4112 0.057 Uiso 1 1 calc R . .
C14 C 0.8007(8) -0.3546(9) 0.5006(5) 0.0405(15) Uani 1 1 d . . .
C15 C 0.9366(8) -0.2969(8) 0.5085(5) 0.0387(14) Uani 1 1 d . . .
H15 H 1.0002 -0.3369 0.5680 0.046 Uiso 1 1 calc R . .
C16 C 0.9820(7) -0.1786(8) 0.4286(5) 0.0362(13) Uani 1 1 d . . .
C17 C 1.1258(7) -0.1256(9) 0.4433(5) 0.0396(15) Uani 1 1 d . . .
H17 H 1.1766 -0.1683 0.5070 0.048 Uiso 1 1 calc R . .
C18 C 1.3816(7) 0.1242(8) 0.3465(5) 0.0351(13) Uani 1 1 d . . .
C19 C 1.5950(10) 0.2779(11) 0.3139(7) 0.060(2) Uani 1 1 d . . .
H19A H 1.6190 0.3391 0.3523 0.091 Uiso 1 1 calc R . .
H19B H 1.5222 0.3435 0.2577 0.091 Uiso 1 1 calc R . .
H19C H 1.7002 0.2274 0.2890 0.091 Uiso 1 1 calc R . .
N1 N 1.2706(6) -0.0821(7) 0.1478(4) 0.0407(13) Uani 1 1 d . . .
N2 N 1.0392(6) 0.1840(7) 0.0924(4) 0.0414(13) Uani 1 1 d . . .
N3 N 0.7615(7) -0.4795(8) 0.5831(5) 0.0481(15) Uani 1 1 d . . .
N4 N 1.1919(6) -0.0252(6) 0.3777(4) 0.0317(11) Uani 1 1 d . . .
N5 N 1.3271(6) 0.0090(7) 0.4130(4) 0.0395(13) Uani 1 1 d . . .
N6 N 1.5115(7) 0.1648(9) 0.3769(4) 0.0486(15) Uani 1 1 d D . .
H6A H 1.553(9) 0.121(10) 0.435(3) 0.058 Uiso 1 1 d D . .
O1 O 0.9156(5) -0.0132(7) 0.2598(3) 0.0483(14) Uani 1 1 d . . .
O2 O 0.6461(7) -0.5377(9) 0.5736(5) 0.079(2) Uani 1 1 d . . .
O3 O 0.8470(7) -0.5285(8) 0.6601(4) 0.0626(15) Uani 1 1 d . . .
S1 S 1.2977(2) 0.2228(2) 0.22666(13) 0.0486(5) Uani 1 1 d . . .
Cu1 Cu 1.11863(8) 0.06878(9) 0.23728(5) 0.0355(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.352(9) . ?
C1 C2 1.364(12) . ?
C1 H1 0.9300 . ?
C2 C3 1.339(14) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(10) . ?
C4 H4 0.9300 . ?
C5 N2 1.320(9) . ?
C5 C6 1.507(10) . ?
C6 N1 1.323(9) . ?
C6 C7 1.378(10) . ?
C7 C8 1.375(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.357(14) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(11) . ?
C9 H9 0.9300 . ?
C10 N1 1.328(9) . ?
C10 H10 0.9300 . ?
C11 O1 1.283(7) . ?
C11 C16 1.422(9) . ?
C11 C12 1.424(9) . ?
C12 C13 1.368(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.365(10) . ?
C14 N3 1.437(9) . ?
C15 C16 1.399(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.424(10) . ?
C17 N4 1.278(9) . ?
C17 H17 0.9300 . ?
C18 N5 1.325(8) . ?
C18 N6 1.341(9) . ?
C18 S1 1.728(6) . ?
C19 N6 1.422(9) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N1 Cu1 2.253(6) . ?
N2 Cu1 2.031(6) . ?
N3 O3 1.218(8) . ?
N3 O2 1.227(9) . ?
N4 N5 1.377(8) . ?
N4 Cu1 1.944(5) . ?
N6 H6A 0.84(5) . ?
O1 Cu1 1.942(5) . ?
S1 Cu1 2.253(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
N2 C1 C2 122.0(9) . . ?
N2 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 118.6(8) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121.0(7) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 117.3(8) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
N2 C5 C4 121.5(7) . . ?
N2 C5 C6 115.9(5) . . ?
C4 C5 C6 122.6(7) . . ?
N1 C6 C7 123.6(7) . . ?
N1 C6 C5 115.2(6) . . ?
C7 C6 C5 121.2(6) . . ?
C8 C7 C6 117.0(7) . . ?
C8 C7 H7 121.5 . . ?
C6 C7 H7 121.5 . . ?
C9 C8 C7 120.8(7) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 117.9(8) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
N1 C10 C9 122.5(7) . . ?
N1 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
O1 C11 C16 123.6(6) . . ?
O1 C11 C12 118.6(6) . . ?
C16 C11 C12 117.8(6) . . ?
C13 C12 C11 122.3(6) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C14 118.4(7) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C15 C14 C13 121.9(7) . . ?
C15 C14 N3 119.5(6) . . ?
C13 C14 N3 118.7(7) . . ?
C14 C15 C16 121.2(6) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 118.5(6) . . ?
C15 C16 C17 117.4(6) . . ?
C11 C16 C17 124.1(6) . . ?
N4 C17 C16 126.5(6) . . ?
N4 C17 H17 116.8 . . ?
C16 C17 H17 116.8 . . ?
N5 C18 N6 116.0(6) . . ?
N5 C18 S1 125.0(5) . . ?
N6 C18 S1 119.1(5) . . ?
N6 C19 H19A 109.5 . . ?
N6 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N6 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6 N1 C10 118.1(6) . . ?
C6 N1 Cu1 112.6(5) . . ?
C10 N1 Cu1 129.0(5) . . ?
C5 N2 C1 119.4(6) . . ?
C5 N2 Cu1 120.0(4) . . ?
C1 N2 Cu1 120.5(5) . . ?
O3 N3 O2 121.3(7) . . ?
O3 N3 C14 119.3(6) . . ?
O2 N3 C14 119.4(6) . . ?
C17 N4 N5 114.6(5) . . ?
C17 N4 Cu1 124.2(5) . . ?
N5 N4 Cu1 121.2(4) . . ?
C18 N5 N4 113.0(5) . . ?
C18 N6 C19 124.1(6) . . ?
C18 N6 H6A 121(6) . . ?
C19 N6 H6A 115(6) . . ?
C11 O1 Cu1 126.6(4) . . ?
C18 S1 Cu1 94.4(2) . . ?
O1 Cu1 N4 93.6(2) . . ?
O1 Cu1 N2 88.3(2) . . ?
N4 Cu1 N2 175.3(2) . . ?
O1 Cu1 S1 162.04(19) . . ?
N4 Cu1 S1 85.46(17) . . ?
N2 Cu1 S1 91.37(18) . . ?
O1 Cu1 N1 98.0(2) . . ?
N4 Cu1 N1 107.81(19) . . ?
N2 Cu1 N1 76.1(2) . . ?
S1 Cu1 N1 99.36(16) . . ?

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
N2 C1 C2 C3 0.4(14) . . . . ?
C1 C2 C3 C4 -0.2(15) . . . . ?
C2 C3 C4 C5 -0.7(14) . . . . ?
C3 C4 C5 N2 1.5(12) . . . . ?
C3 C4 C5 C6 -179.6(7) . . . . ?
N2 C5 C6 N1 2.1(9) . . . . ?
C4 C5 C6 N1 -176.8(7) . . . . ?
N2 C5 C6 C7 -176.2(8) . . . . ?
C4 C5 C6 C7 4.9(12) . . . . ?
N1 C6 C7 C8 -1.3(13) . . . . ?
C5 C6 C7 C8 176.9(7) . . . . ?
C6 C7 C8 C9 2.5(15) . . . . ?
C7 C8 C9 C10 -1.1(16) . . . . ?
C8 C9 C10 N1 -1.6(14) . . . . ?
O1 C11 C12 C13 176.0(7) . . . . ?
C16 C11 C12 C13 -2.6(10) . . . . ?
C11 C12 C13 C14 1.7(11) . . . . ?
C12 C13 C14 C15 0.6(11) . . . . ?
C12 C13 C14 N3 -179.4(7) . . . . ?
C13 C14 C15 C16 -2.0(10) . . . . ?
N3 C14 C15 C16 178.1(6) . . . . ?
C14 C15 C16 C11 0.9(9) . . . . ?
C14 C15 C16 C17 -179.9(6) . . . . ?
O1 C11 C16 C15 -177.2(6) . . . . ?
C12 C11 C16 C15 1.3(9) . . . . ?
O1 C11 C16 C17 3.6(10) . . . . ?
C12 C11 C16 C17 -177.9(6) . . . . ?
C15 C16 C17 N4 175.9(6) . . . . ?
C11 C16 C17 N4 -4.9(10) . . . . ?
C7 C6 N1 C10 -1.3(12) . . . . ?
C5 C6 N1 C10 -179.6(6) . . . . ?
C7 C6 N1 Cu1 173.7(7) . . . . ?
C5 C6 N1 Cu1 -4.6(8) . . . . ?
C9 C10 N1 C6 2.8(12) . . . . ?
C9 C10 N1 Cu1 -171.3(7) . . . . ?
C4 C5 N2 C1 -1.4(11) . . . . ?
C6 C5 N2 C1 179.6(7) . . . . ?
C4 C5 N2 Cu1 -179.1(6) . . . . ?
C6 C5 N2 Cu1 1.9(8) . . . . ?
C2 C1 N2 C5 0.4(12) . . . . ?
C2 C1 N2 Cu1 178.1(7) . . . . ?
C15 C14 N3 O3 2.3(10) . . . . ?
C13 C14 N3 O3 -177.7(7) . . . . ?
C15 C14 N3 O2 -175.5(7) . . . . ?
C13 C14 N3 O2 4.5(10) . . . . ?
C16 C17 N4 N5 177.8(6) . . . . ?
C16 C17 N4 Cu1 -4.6(9) . . . . ?
N6 C18 N5 N4 179.0(5) . . . . ?
S1 C18 N5 N4 -0.8(8) . . . . ?
C17 N4 N5 C18 -173.7(5) . . . . ?
Cu1 N4 N5 C18 8.7(7) . . . . ?
N5 C18 N6 C19 175.4(7) . . . . ?
S1 C18 N6 C19 -4.8(10) . . . . ?
C16 C11 O1 Cu1 7.0(9) . . . . ?
C12 C11 O1 Cu1 -171.4(5) . . . . ?
N5 C18 S1 Cu1 -5.4(5) . . . . ?
N6 C18 S1 Cu1 174.8(5) . . . . ?
C11 O1 Cu1 N4 -12.1(6) . . . . ?
C11 O1 Cu1 N2 172.1(6) . . . . ?
C11 O1 Cu1 S1 -98.6(7) . . . . ?
C11 O1 Cu1 N1 96.4(6) . . . . ?
C17 N4 Cu1 O1 10.7(5) . . . . ?
N5 N4 Cu1 O1 -171.9(4) . . . . ?
C17 N4 Cu1 S1 172.7(5) . . . . ?
N5 N4 Cu1 S1 -9.9(4) . . . . ?
C17 N4 Cu1 N1 -88.9(5) . . . . ?
N5 N4 Cu1 N1 88.5(5) . . . . ?
C5 N2 Cu1 O1 -102.0(6) . . . . ?
C1 N2 Cu1 O1 80.4(6) . . . . ?
C5 N2 Cu1 S1 96.0(5) . . . . ?
C1 N2 Cu1 S1 -81.6(6) . . . . ?
C5 N2 Cu1 N1 -3.3(5) . . . . ?
C1 N2 Cu1 N1 179.1(6) . . . . ?
C18 S1 Cu1 O1 94.6(5) . . . . ?
C18 S1 Cu1 N4 6.8(2) . . . . ?
C18 S1 Cu1 N2 -176.7(2) . . . . ?
C18 S1 Cu1 N1 -100.5(2) . . . . ?
C6 N1 Cu1 O1 90.5(5) . . . . ?
C10 N1 Cu1 O1 -95.2(6) . . . . ?
C6 N1 Cu1 N4 -173.0(5) . . . . ?
C10 N1 Cu1 N4 1.3(7) . . . . ?
C6 N1 Cu1 N2 4.3(5) . . . . ?
C10 N1 Cu1 N2 178.6(7) . . . . ?
C6 N1 Cu1 S1 -84.8(5) . . . . ?
C10 N1 Cu1 S1 89.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.908
_diffrn_reflns_theta_full        27.68
_diffrn_measured_fraction_theta_full 0.908
_refine_diff_density_max         2.872
_refine_diff_density_min         -1.818
_refine_diff_density_rms         0.270

# start Validation Reply Form
_vrf_PLAT029_shelxl              
;
RESPONSE: This Alert is due to maximum thermal vibrations and 
low quality of crystals which lead to give weak reflections
 or incomplete data set. 
;
_vrf_PLAT973_shelxl              
;
RESPONSE: This Alert is due to a peak of large
electron density which is very
close to the central metal atom. This high electron 
density may be due to
maximum thermal vibrations during data collection. 
;
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1028088'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;
_audit_creation_date             2014-12-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 Cu N6 O3 S'
_chemical_formula_sum            'C21 H16 Cu N6 O3 S'
_chemical_formula_weight         496.00
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   5.9763(5)
_cell_length_b                   11.6828(10)
_cell_length_c                   14.3427(8)
_cell_angle_alpha                85.970(6)
_cell_angle_beta                 83.926(6)
_cell_angle_gamma                82.198(7)
_cell_volume                     984.98(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3650
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.7580
_cell_measurement_theta_min      3.5140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.255
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             506
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10987
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         32.741
_diffrn_reflns_theta_min         3.275
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_device_type  'Agilent, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5296
_reflns_number_total             6505
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
__computing_cell_refinement      
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         6505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+0.4480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0984
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.13504(4) 0.79551(2) 0.13372(2) 0.01930(7) Uani 1 1 d . . . . .
S1 S 0.04846(8) 0.76191(4) -0.01137(3) 0.02312(10) Uani 1 1 d . . . . .
O1 O 0.2900(2) 0.86533(12) 0.22576(10) 0.0253(3) Uani 1 1 d . . . . .
O2 O 0.0146(3) 1.21402(15) 0.53810(11) 0.0386(4) Uani 1 1 d . . . . .
O3 O -0.2883(3) 1.24226(16) 0.46580(12) 0.0437(4) Uani 1 1 d . . . . .
N1 N -0.1026(3) 0.92706(13) 0.12817(11) 0.0194(3) Uani 1 1 d . . . . .
N2 N -0.2493(3) 0.93990(14) 0.05922(11) 0.0213(3) Uani 1 1 d . . . . .
N3 N -0.3295(3) 0.87331(15) -0.07611(12) 0.0273(4) Uani 1 1 d . . . . .
H3 H -0.4408 0.9309 -0.0760 0.033 Uiso 1 1 calc R . . . .
N4 N -0.0480(3) 0.68641(14) 0.24668(11) 0.0213(3) Uani 1 1 d . . . . .
N5 N 0.3569(3) 0.64996(13) 0.14381(11) 0.0195(3) Uani 1 1 d . . . . .
N6 N -0.0950(3) 1.19396(15) 0.47485(12) 0.0279(4) Uani 1 1 d . . . . .
C1 C -0.1893(3) 0.86614(16) -0.00756(13) 0.0202(3) Uani 1 1 d . . . . .
C2 C -0.1545(3) 0.99838(16) 0.19421(13) 0.0225(4) Uani 1 1 d . . . . .
H2 H -0.2918 1.0496 0.1916 0.027 Uiso 1 1 calc R . . . .
C3 C -0.0234(3) 1.00748(16) 0.27140(13) 0.0204(3) Uani 1 1 d . . . . .
C4 C -0.1146(3) 1.08829(16) 0.33615(13) 0.0224(4) Uani 1 1 d . . . . .
H4 H -0.2624 1.1284 0.3310 0.027 Uiso 1 1 calc R . . . .
C5 C 0.0072(3) 1.11122(16) 0.40812(13) 0.0226(4) Uani 1 1 d . . . . .
C6 C 0.2281(4) 1.05577(18) 0.41644(14) 0.0257(4) Uani 1 1 d . . . . .
H6 H 0.3131 1.0742 0.4644 0.031 Uiso 1 1 calc R . . . .
C7 C 0.3186(3) 0.97455(18) 0.35399(14) 0.0251(4) Uani 1 1 d . . . . .
H7 H 0.4680 0.9368 0.3597 0.030 Uiso 1 1 calc R . . . .
C8 C 0.1977(3) 0.94408(16) 0.28052(13) 0.0206(3) Uani 1 1 d . . . . .
C9 C 0.5506(3) 0.62990(19) 0.08950(15) 0.0277(4) Uani 1 1 d . . . . .
H9 H 0.5852 0.6852 0.0401 0.033 Uiso 1 1 calc R . . . .
C10 C 0.7059(4) 0.5304(2) 0.10222(17) 0.0349(5) Uani 1 1 d . . . . .
H10 H 0.8414 0.5181 0.0612 0.042 Uiso 1 1 calc R . . . .
C11 C 0.6620(4) 0.45241(19) 0.17284(17) 0.0323(5) Uani 1 1 d . . . . .
H11 H 0.7679 0.3854 0.1826 0.039 Uiso 1 1 calc R . . . .
C12 C 0.4586(3) 0.47008(16) 0.23255(14) 0.0253(4) Uani 1 1 d . . . . .
C13 C 0.3998(4) 0.39302(18) 0.31028(16) 0.0339(5) Uani 1 1 d . . . . .
H13 H 0.5031 0.3264 0.3244 0.041 Uiso 1 1 calc R . . . .
C14 C 0.2025(4) 0.41268(18) 0.36354(16) 0.0338(5) Uani 1 1 d . . . . .
H14 H 0.1691 0.3600 0.4150 0.041 Uiso 1 1 calc R . . . .
C15 C 0.0400(4) 0.51177(18) 0.34465(14) 0.0274(4) Uani 1 1 d . . . . .
C16 C -0.1742(4) 0.5345(2) 0.39595(15) 0.0346(5) Uani 1 1 d . . . . .
H16 H -0.2183 0.4835 0.4471 0.042 Uiso 1 1 calc R . . . .
C17 C -0.3180(4) 0.6307(2) 0.37135(16) 0.0350(5) Uani 1 1 d . . . . .
H17 H -0.4630 0.6472 0.4052 0.042 Uiso 1 1 calc R . . . .
C18 C -0.2492(3) 0.7043(2) 0.29589(15) 0.0280(4) Uani 1 1 d . . . . .
H18 H -0.3513 0.7702 0.2790 0.034 Uiso 1 1 calc R . . . .
C19 C 0.0942(3) 0.59104(16) 0.27069(13) 0.0197(3) Uani 1 1 d . . . . .
C20 C 0.3077(3) 0.57085(15) 0.21419(13) 0.0190(3) Uani 1 1 d . . . . .
C21 C -0.3102(4) 0.79371(19) -0.14919(14) 0.0298(4) Uani 1 1 d . . . . .
H21A H -0.4068 0.8263 -0.1982 0.045 Uiso 1 1 calc GR . . . .
H21B H -0.3587 0.7203 -0.1230 0.045 Uiso 1 1 calc GR . . . .
H21C H -0.1520 0.7802 -0.1763 0.045 Uiso 1 1 calc GR . . . .


_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 S1 2.2694(5) . ?
Cu1 O1 1.9699(14) . ?
Cu1 N1 1.9492(15) . ?
Cu1 N4 2.2714(17) . ?
Cu1 N5 2.0161(15) . ?
S1 C1 1.7401(18) . ?
O1 C8 1.280(2) . ?
O2 N6 1.227(2) . ?
O3 N6 1.230(2) . ?
N1 N2 1.377(2) . ?
N1 C2 1.291(2) . ?
N2 C1 1.322(2) . ?
N3 H3 0.8800 . ?
N3 C1 1.349(2) . ?
N3 C21 1.435(3) . ?
N4 C18 1.327(2) . ?
N4 C19 1.354(2) . ?
N5 C9 1.328(2) . ?
N5 C20 1.356(2) . ?
N6 C5 1.439(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.440(2) . ?
C3 C4 1.388(3) . ?
C3 C8 1.439(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 C6 1.403(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.368(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.429(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.400(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.343(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.411(3) . ?
C12 C13 1.428(3) . ?
C12 C20 1.410(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.337(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.436(3) . ?
C15 C16 1.409(3) . ?
C15 C19 1.400(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.368(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.397(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.437(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
S1 Cu1 N4 111.19(4) . . ?
O1 Cu1 S1 156.03(5) . . ?
O1 Cu1 N4 92.75(6) . . ?
O1 Cu1 N5 89.79(6) . . ?
N1 Cu1 S1 85.34(5) . . ?
N1 Cu1 O1 92.96(6) . . ?
N1 Cu1 N4 97.38(6) . . ?
N1 Cu1 N5 174.46(7) . . ?
N5 Cu1 S1 94.09(5) . . ?
N5 Cu1 N4 77.67(6) . . ?
C1 S1 Cu1 93.84(6) . . ?
C8 O1 Cu1 125.42(12) . . ?
N2 N1 Cu1 121.21(12) . . ?
C2 N1 Cu1 123.22(12) . . ?
C2 N1 N2 114.91(15) . . ?
C1 N2 N1 113.11(15) . . ?
C1 N3 H3 117.6 . . ?
C1 N3 C21 124.71(17) . . ?
C21 N3 H3 117.6 . . ?
C18 N4 Cu1 132.67(14) . . ?
C18 N4 C19 117.73(18) . . ?
C19 N4 Cu1 109.26(12) . . ?
C9 N5 Cu1 124.36(14) . . ?
C9 N5 C20 118.68(16) . . ?
C20 N5 Cu1 116.87(12) . . ?
O2 N6 O3 122.69(18) . . ?
O2 N6 C5 118.65(18) . . ?
O3 N6 C5 118.66(17) . . ?
N2 C1 S1 125.16(14) . . ?
N2 C1 N3 115.67(16) . . ?
N3 C1 S1 119.15(14) . . ?
N1 C2 H2 117.0 . . ?
N1 C2 C3 126.00(17) . . ?
C3 C2 H2 117.0 . . ?
C4 C3 C2 116.38(16) . . ?
C4 C3 C8 119.74(17) . . ?
C8 C3 C2 123.74(17) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.89(17) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 N6 119.17(17) . . ?
C4 C5 C6 121.09(17) . . ?
C6 C5 N6 119.73(17) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 C5 118.58(18) . . ?
C7 C6 H6 120.7 . . ?
C6 C7 H7 118.6 . . ?
C6 C7 C8 122.78(18) . . ?
C8 C7 H7 118.6 . . ?
O1 C8 C3 123.51(17) . . ?
O1 C8 C7 119.70(17) . . ?
C7 C8 C3 116.77(17) . . ?
N5 C9 H9 118.7 . . ?
N5 C9 C10 122.5(2) . . ?
C10 C9 H9 118.7 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 119.99(19) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 123.83(19) . . ?
C20 C12 C11 117.35(19) . . ?
C20 C12 C13 118.82(19) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.39(19) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.4(2) . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 124.0(2) . . ?
C19 C15 C14 118.8(2) . . ?
C19 C15 C16 117.2(2) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.3(2) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.2(2) . . ?
C18 C17 H17 120.4 . . ?
N4 C18 C17 123.1(2) . . ?
N4 C18 H18 118.4 . . ?
C17 C18 H18 118.4 . . ?
N4 C19 C15 123.35(18) . . ?
N4 C19 C20 116.85(16) . . ?
C15 C19 C20 119.77(17) . . ?
N5 C20 C12 121.87(17) . . ?
N5 C20 C19 118.45(15) . . ?
C12 C20 C19 119.67(17) . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
N3 H3 N2 0.88 2.23 3.100(2) 171.2 2_475
C13 H13 O3 0.95 2.56 3.315(3) 136.6 1_645
C14 H14 O2 0.95 2.56 3.494(3) 169.4 1_545
C17 H17 O3 0.95 2.56 3.402(3) 148.4 2_476
C18 H18 O1 0.95 2.45 3.324(2) 153.3 1_455

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
Cu1 S1 C1 N2 7.08(18) . . . . ?
Cu1 S1 C1 N3 -171.62(16) . . . . ?
Cu1 O1 C8 C3 -11.3(3) . . . . ?
Cu1 O1 C8 C7 170.25(14) . . . . ?
Cu1 N1 N2 C1 -9.7(2) . . . . ?
Cu1 N1 C2 C3 12.9(3) . . . . ?
Cu1 N4 C18 C17 -171.58(15) . . . . ?
Cu1 N4 C19 C15 173.76(15) . . . . ?
Cu1 N4 C19 C20 -8.15(19) . . . . ?
Cu1 N5 C9 C10 176.39(16) . . . . ?
Cu1 N5 C20 C12 -175.05(14) . . . . ?
Cu1 N5 C20 C19 5.4(2) . . . . ?
O2 N6 C5 C4 -179.68(19) . . . . ?
O2 N6 C5 C6 -0.1(3) . . . . ?
O3 N6 C5 C4 -0.1(3) . . . . ?
O3 N6 C5 C6 179.42(19) . . . . ?
N1 N2 C1 S1 0.0(2) . . . . ?
N1 N2 C1 N3 178.77(17) . . . . ?
N1 C2 C3 C4 -178.2(2) . . . . ?
N1 C2 C3 C8 6.1(3) . . . . ?
N2 N1 C2 C3 -176.39(18) . . . . ?
N4 C19 C20 N5 2.7(3) . . . . ?
N4 C19 C20 C12 -176.84(16) . . . . ?
N5 C9 C10 C11 -1.3(3) . . . . ?
N6 C5 C6 C7 177.80(19) . . . . ?
C2 N1 N2 C1 179.37(17) . . . . ?
C2 C3 C4 C5 -174.11(18) . . . . ?
C2 C3 C8 O1 -7.0(3) . . . . ?
C2 C3 C8 C7 171.57(19) . . . . ?
C3 C4 C5 N6 -178.81(18) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C4 C3 C8 O1 177.43(18) . . . . ?
C4 C3 C8 C7 -4.0(3) . . . . ?
C4 C5 C6 C7 -2.6(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 O1 -178.32(19) . . . . ?
C6 C7 C8 C3 3.1(3) . . . . ?
C8 C3 C4 C5 1.8(3) . . . . ?
C9 N5 C20 C12 1.7(3) . . . . ?
C9 N5 C20 C19 -177.86(18) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C10 C11 C12 C13 -178.8(2) . . . . ?
C10 C11 C12 C20 0.4(3) . . . . ?
C11 C12 C13 C14 -178.6(2) . . . . ?
C11 C12 C20 N5 -1.8(3) . . . . ?
C11 C12 C20 C19 177.72(18) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C12 C20 N5 177.39(18) . . . . ?
C13 C12 C20 C19 -3.1(3) . . . . ?
C13 C14 C15 C16 177.4(2) . . . . ?
C13 C14 C15 C19 -2.2(3) . . . . ?
C14 C15 C16 C17 -179.1(2) . . . . ?
C14 C15 C19 N4 179.33(18) . . . . ?
C14 C15 C19 C20 1.3(3) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C15 C19 C20 N5 -179.12(17) . . . . ?
C15 C19 C20 C12 1.3(3) . . . . ?
C16 C15 C19 N4 -0.3(3) . . . . ?
C16 C15 C19 C20 -178.30(18) . . . . ?
C16 C17 C18 N4 -0.8(3) . . . . ?
C18 N4 C19 C15 -0.5(3) . . . . ?
C18 N4 C19 C20 177.61(17) . . . . ?
C19 N4 C18 C17 1.0(3) . . . . ?
C19 C15 C16 C17 0.5(3) . . . . ?
C20 N5 C9 C10 -0.1(3) . . . . ?
C20 C12 C13 C14 2.2(3) . . . . ?
C21 N3 C1 S1 6.0(3) . . . . ?
C21 N3 C1 N2 -172.8(2) . . . . ?

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1028089'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 Cu N6 O3 S, 3(O)'
_chemical_formula_sum            'C20 H24 Cu N6 O6 S'
_chemical_formula_weight         540.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1557(18)
_cell_length_b                   11.023(3)
_cell_length_c                   14.092(3)
_cell_angle_alpha                104.400(13)
_cell_angle_beta                 93.284(13)
_cell_angle_gamma                99.663(14)
_cell_volume                     1203.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5358
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      25.96


_exptl_crystal_description       Rectangular
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             558
_exptl_absorpt_coefficient_mu    1.042
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5656
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23381
_diffrn_reflns_av_R_equivalents  0.1109
_diffrn_reflns_av_sigmaI/netI    0.1355
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         31.18
_reflns_number_total             7133
_reflns_number_gt                3191
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
This complex is highly
 disordered due to thermal vibrations in oxygen atoms of nitro 
group and lattice water molecules. The disorder has been applied
on oxygen atoms of nitro group and lattice water molecules resulting 
improvement in refined resulting structure.  
In the presence of highly disordered lattice water molecules, their protons  
could not be located from difference Fourier map. 
DFIX, OMIT and BUMP commands are the restraints used during 
structure refinement. DFIX command used to fix distance of protons
 of -NH group to their N atoms. OMIT command is used to suppresses
 all unnecessary reflections those who are truncated by beam stop. BUMP
 is used for solvent water to suppress unnecessary weak interactions.  

 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1393P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7133
_refine_ls_number_parameters     336
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1598
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.2624
_refine_ls_wR_factor_gt          0.2088
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.960
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.003

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1243(6) 0.9788(5) 0.3133(4) 0.0468(12) Uani 1 1 d . . .
H1 H 0.1039 0.9997 0.2543 0.056 Uiso 1 1 calc R . .
C2 C 0.0423(7) 0.8644(6) 0.3241(5) 0.0598(15) Uani 1 1 d . . .
H2 H -0.0325 0.8087 0.2734 0.072 Uiso 1 1 calc R . .
C3 C 0.0731(8) 0.8345(6) 0.4105(5) 0.0685(17) Uani 1 1 d . . .
H3 H 0.0179 0.7577 0.4192 0.082 Uiso 1 1 calc R . .
C4 C 0.1846(7) 0.9160(5) 0.4853(4) 0.0540(14) Uani 1 1 d . . .
H4 H 0.2074 0.8953 0.5442 0.065 Uiso 1 1 calc R . .
C5 C 0.2619(6) 1.0308(5) 0.4694(4) 0.0397(11) Uani 1 1 d . . .
C6 C 0.3821(6) 1.1279(5) 0.5445(4) 0.0401(11) Uani 1 1 d . . .
C7 C 0.4303(7) 1.1119(6) 0.6365(4) 0.0549(14) Uani 1 1 d . . .
H7 H 0.3881 1.0370 0.6531 0.066 Uiso 1 1 calc R . .
C8 C 0.5415(7) 1.2083(6) 0.7028(4) 0.0616(16) Uani 1 1 d . . .
H8 H 0.5742 1.1988 0.7644 0.074 Uiso 1 1 calc R . .
C9 C 0.6025(7) 1.3168(6) 0.6775(4) 0.0581(15) Uani 1 1 d . . .
H9 H 0.6761 1.3830 0.7217 0.070 Uiso 1 1 calc R . .
C10 C 0.5532(6) 1.3270(5) 0.5850(4) 0.0483(13) Uani 1 1 d . . .
H10 H 0.5971 1.4006 0.5670 0.058 Uiso 1 1 calc R . .
C11 C 0.7035(8) 1.1192(7) 0.0565(4) 0.0628(17) Uani 1 1 d . A .
C12 C 0.8043(7) 1.0995(6) 0.1322(4) 0.0564(15) Uani 1 1 d . . .
H12 H 0.9012 1.0669 0.1194 0.068 Uiso 1 1 calc R . .
C13 C 0.7580(6) 1.1290(6) 0.2260(4) 0.0516(14) Uani 1 1 d . . .
H13 H 0.8254 1.1159 0.2766 0.062 Uiso 1 1 calc R . .
C14 C 0.6116(6) 1.1787(5) 0.2488(4) 0.0407(11) Uani 1 1 d . . .
C15 C 0.5148(6) 1.2006(5) 0.1702(4) 0.0472(13) Uani 1 1 d . . .
C16 C 0.5645(8) 1.1706(7) 0.0751(4) 0.0634(17) Uani 1 1 d . . .
H16 H 0.5015 1.1860 0.0238 0.076 Uiso 1 1 calc R . .
C17 C 0.3674(6) 1.2581(5) 0.1810(4) 0.0474(13) Uani 1 1 d . . .
H17 H 0.3165 1.2718 0.1249 0.057 Uiso 1 1 calc R . .
C18 C 0.1046(6) 1.3926(5) 0.3370(4) 0.0390(11) Uani 1 1 d . . .
C19 C -0.1042(7) 1.4728(6) 0.2467(4) 0.0522(14) Uani 1 1 d . . .
H19A H -0.1326 1.3922 0.1968 0.063 Uiso 1 1 calc R . .
H19B H -0.0265 1.5310 0.2216 0.063 Uiso 1 1 calc R . .
C20 C -0.2598(7) 1.5267(6) 0.2684(5) 0.0617(16) Uani 1 1 d . . .
H20A H -0.3345 1.4706 0.2958 0.092 Uiso 1 1 calc R . .
H20B H -0.3138 1.5348 0.2086 0.092 Uiso 1 1 calc R . .
H20C H -0.2304 1.6090 0.3147 0.092 Uiso 1 1 calc R . .
N1 N 0.2325(5) 1.0613(4) 0.3846(3) 0.0404(9) Uani 1 1 d . . .
N2 N 0.4452(5) 1.2357(4) 0.5204(3) 0.0395(9) Uani 1 1 d . . .
N3 N -0.0258(5) 1.4536(5) 0.3359(3) 0.0494(11) Uani 1 1 d D . .
H3A H -0.078(6) 1.472(5) 0.387(3) 0.059 Uiso 1 1 d D . .
N4 N 0.1656(5) 1.3538(4) 0.2536(3) 0.0425(10) Uani 1 1 d . . .
N5 N 0.3007(4) 1.2919(4) 0.2622(3) 0.0367(9) Uani 1 1 d . . .
N6 N 0.7533(8) 1.0896(7) -0.0428(4) 0.094(2) Uani 1 1 d D . .
O1 O 0.714(6) 1.163(4) -0.092(2) 0.089(5) Uani 0.28(4) 1 d PD A 1
O2 O 0.908(2) 1.086(3) -0.0464(17) 0.084(4) Uani 0.299(19) 1 d PD A 1
O1' O 0.659(2) 1.104(2) -0.1110(8) 0.089(5) Uani 0.72(4) 1 d PD A 2
O2' O 0.8473(15) 1.0120(13) -0.0645(7) 0.084(4) Uani 0.701(19) 1 d PD A 2
O1W O 1.334(4) 1.523(2) 0.0283(10) 0.51(3) Uani 0.925(18) 1 d P B 1
O1W' O 1.08(2) 1.17(2) -0.016(11) 0.51(3) Uani 0.075(18) 1 d P B 2
O3 O 0.5749(4) 1.2038(4) 0.3390(3) 0.0483(9) Uani 1 1 d . . .
O2W O 1.249(6) 1.519(7) 0.040(4) 0.266(13) Uani 0.40(2) 1 d P B 1
O3W O 1.227(3) 1.2751(17) -0.0739(10) 0.142(6) Uani 0.66(2) 1 d P C 1
O2W' O 1.125(4) 1.407(3) 0.026(2) 0.266(13) Uani 0.60(2) 1 d P B 2
O3W' O 1.134(6) 1.310(4) -0.047(2) 0.142(6) Uani 0.34(2) 1 d P B 2
S1 S 0.17968(18) 1.37575(14) 0.45055(10) 0.0502(4) Uani 1 1 d . . .
Cu1 Cu 0.36951(7) 1.25598(5) 0.38632(4) 0.0381(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.337(6) . ?
C1 C2 1.373(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.360(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(7) . ?
C4 H4 0.9300 . ?
C5 N1 1.339(6) . ?
C5 C6 1.481(7) . ?
C6 N2 1.344(6) . ?
C6 C7 1.395(7) . ?
C7 C8 1.382(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.355(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(7) . ?
C9 H9 0.9300 . ?
C10 N2 1.331(6) . ?
C10 H10 0.9300 . ?
C11 C16 1.361(7) . ?
C11 C12 1.391(7) . ?
C11 N6 1.452(7) . ?
C12 C13 1.371(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.416(7) . ?
C13 H13 0.9300 . ?
C14 O3 1.295(6) . ?
C14 C15 1.416(7) . ?
C15 C16 1.398(7) . ?
C15 C17 1.449(7) . ?
C16 H16 0.9300 . ?
C17 N5 1.292(6) . ?
C17 H17 0.9300 . ?
C18 N4 1.303(6) . ?
C18 N3 1.352(6) . ?
C18 S1 1.745(5) . ?
C19 N3 1.455(7) . ?
C19 C20 1.504(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 Cu1 2.241(4) . ?
N2 Cu1 2.031(4) . ?
N3 H3A 0.86(4) . ?
N4 N5 1.405(5) . ?
N5 Cu1 1.959(4) . ?
N6 O2' 1.236(8) . ?
N6 O1' 1.255(10) . ?
N6 O1 1.261(18) . ?
N6 O2 1.271(16) . ?
O1W O2W 0.72(6) . ?
O1W' O3W' 1.70(15) . ?
O3 Cu1 1.961(3) . ?
O2W' O3W' 1.30(4) . ?
S1 Cu1 2.2828(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.4(5) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 118.4(6) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 121.1(6) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 117.3(6) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
N1 C5 C4 122.2(5) . . ?
N1 C5 C6 115.1(4) . . ?
C4 C5 C6 122.7(5) . . ?
N2 C6 C7 120.1(5) . . ?
N2 C6 C5 116.7(4) . . ?
C7 C6 C5 123.2(5) . . ?
C8 C7 C6 119.4(5) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C7 119.6(5) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 118.7(5) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
N2 C10 C9 122.5(5) . . ?
N2 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C16 C11 C12 120.9(5) . . ?
C16 C11 N6 120.1(5) . . ?
C12 C11 N6 118.9(5) . . ?
C13 C12 C11 118.7(5) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 122.6(5) . . ?
C12 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
O3 C14 C13 119.3(4) . . ?
O3 C14 C15 123.7(4) . . ?
C13 C14 C15 117.0(5) . . ?
C16 C15 C14 119.6(5) . . ?
C16 C15 C17 115.9(5) . . ?
C14 C15 C17 124.5(5) . . ?
C11 C16 C15 121.1(5) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
N5 C17 C15 125.5(5) . . ?
N5 C17 H17 117.2 . . ?
C15 C17 H17 117.2 . . ?
N4 C18 N3 117.3(5) . . ?
N4 C18 S1 125.6(4) . . ?
N3 C18 S1 117.1(4) . . ?
N3 C19 C20 110.1(5) . . ?
N3 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
N3 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C5 118.7(4) . . ?
C1 N1 Cu1 128.5(4) . . ?
C5 N1 Cu1 112.7(3) . . ?
C10 N2 C6 119.6(4) . . ?
C10 N2 Cu1 121.6(4) . . ?
C6 N2 Cu1 118.8(3) . . ?
C18 N3 C19 123.5(4) . . ?
C18 N3 H3A 120(4) . . ?
C19 N3 H3A 115(4) . . ?
C18 N4 N5 113.1(4) . . ?
C17 N5 N4 113.8(4) . . ?
C17 N5 Cu1 124.8(3) . . ?
N4 N5 Cu1 121.3(3) . . ?
O2' N6 O1' 117.8(10) . . ?
O2' N6 O1 127.0(18) . . ?
O1' N6 O2 124.6(14) . . ?
O1 N6 O2 109(3) . . ?
O2' N6 C11 118.8(6) . . ?
O1' N6 C11 118.3(7) . . ?
O1 N6 C11 113.2(17) . . ?
O2 N6 C11 114.0(12) . . ?
C14 O3 Cu1 126.8(3) . . ?
O2W' O3W' O1W' 111(8) . . ?
C18 S1 Cu1 94.34(16) . . ?
N5 Cu1 O3 93.04(15) . . ?
N5 Cu1 N2 174.95(15) . . ?
O3 Cu1 N2 88.55(15) . . ?
N5 Cu1 N1 107.92(16) . . ?
O3 Cu1 N1 96.88(15) . . ?
N2 Cu1 N1 76.62(15) . . ?
N5 Cu1 S1 84.96(12) . . ?
O3 Cu1 S1 162.80(13) . . ?
N2 Cu1 S1 92.11(12) . . ?
N1 Cu1 S1 99.99(11) . . ?

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
N1 C1 C2 C3 -0.1(9) . . . . ?
C1 C2 C3 C4 -0.5(9) . . . . ?
C2 C3 C4 C5 1.1(9) . . . . ?
C3 C4 C5 N1 -1.0(8) . . . . ?
C3 C4 C5 C6 178.9(5) . . . . ?
N1 C5 C6 N2 1.2(6) . . . . ?
C4 C5 C6 N2 -178.7(5) . . . . ?
N1 C5 C6 C7 -178.9(4) . . . . ?
C4 C5 C6 C7 1.2(8) . . . . ?
N2 C6 C7 C8 0.9(8) . . . . ?
C5 C6 C7 C8 -179.0(5) . . . . ?
C6 C7 C8 C9 -0.2(9) . . . . ?
C7 C8 C9 C10 -0.9(9) . . . . ?
C8 C9 C10 N2 1.5(9) . . . . ?
C16 C11 C12 C13 2.1(11) . . . . ?
N6 C11 C12 C13 179.2(6) . . . . ?
C11 C12 C13 C14 0.0(10) . . . . ?
C12 C13 C14 O3 179.6(5) . . . . ?
C12 C13 C14 C15 -1.7(9) . . . . ?
O3 C14 C15 C16 179.9(5) . . . . ?
C13 C14 C15 C16 1.3(8) . . . . ?
O3 C14 C15 C17 2.6(9) . . . . ?
C13 C14 C15 C17 -176.1(5) . . . . ?
C12 C11 C16 C15 -2.5(11) . . . . ?
N6 C11 C16 C15 -179.6(6) . . . . ?
C14 C15 C16 C11 0.8(10) . . . . ?
C17 C15 C16 C11 178.3(6) . . . . ?
C16 C15 C17 N5 179.5(6) . . . . ?
C14 C15 C17 N5 -3.1(9) . . . . ?
C2 C1 N1 C5 0.2(8) . . . . ?
C2 C1 N1 Cu1 -176.6(4) . . . . ?
C4 C5 N1 C1 0.4(7) . . . . ?
C6 C5 N1 C1 -179.5(4) . . . . ?
C4 C5 N1 Cu1 177.7(4) . . . . ?
C6 C5 N1 Cu1 -2.3(5) . . . . ?
C9 C10 N2 C6 -0.9(8) . . . . ?
C9 C10 N2 Cu1 178.0(4) . . . . ?
C7 C6 N2 C10 -0.3(7) . . . . ?
C5 C6 N2 C10 179.6(4) . . . . ?
C7 C6 N2 Cu1 -179.3(4) . . . . ?
C5 C6 N2 Cu1 0.7(6) . . . . ?
N4 C18 N3 C19 2.6(8) . . . . ?
S1 C18 N3 C19 -178.7(4) . . . . ?
C20 C19 N3 C18 171.9(5) . . . . ?
N3 C18 N4 N5 179.8(4) . . . . ?
S1 C18 N4 N5 1.3(6) . . . . ?
C15 C17 N5 N4 175.6(5) . . . . ?
C15 C17 N5 Cu1 -7.0(8) . . . . ?
C18 N4 N5 C17 -177.0(4) . . . . ?
C18 N4 N5 Cu1 5.6(6) . . . . ?
C16 C11 N6 O2' -159.6(10) . . . . ?
C12 C11 N6 O2' 23.3(13) . . . . ?
C16 C11 N6 O1' -5.2(18) . . . . ?
C12 C11 N6 O1' 177.7(16) . . . . ?
C16 C11 N6 O1 31(3) . . . . ?
C12 C11 N6 O1 -146(3) . . . . ?
C16 C11 N6 O2 156.3(18) . . . . ?
C12 C11 N6 O2 -20.9(19) . . . . ?
C13 C14 O3 Cu1 -173.3(4) . . . . ?
C15 C14 O3 Cu1 8.1(7) . . . . ?
N4 C18 S1 Cu1 -5.8(5) . . . . ?
N3 C18 S1 Cu1 175.7(4) . . . . ?
C17 N5 Cu1 O3 12.5(4) . . . . ?
N4 N5 Cu1 O3 -170.3(3) . . . . ?
C17 N5 Cu1 N1 -85.7(4) . . . . ?
N4 N5 Cu1 N1 91.4(3) . . . . ?
C17 N5 Cu1 S1 175.4(4) . . . . ?
N4 N5 Cu1 S1 -7.5(3) . . . . ?
C14 O3 Cu1 N5 -13.3(4) . . . . ?
C14 O3 Cu1 N2 171.5(4) . . . . ?
C14 O3 Cu1 N1 95.1(4) . . . . ?
C14 O3 Cu1 S1 -96.1(5) . . . . ?
C10 N2 Cu1 O3 82.3(4) . . . . ?
C6 N2 Cu1 O3 -98.8(4) . . . . ?
C10 N2 Cu1 N1 179.7(4) . . . . ?
C6 N2 Cu1 N1 -1.4(3) . . . . ?
C10 N2 Cu1 S1 -80.5(4) . . . . ?
C6 N2 Cu1 S1 98.4(3) . . . . ?
C1 N1 Cu1 N5 1.2(4) . . . . ?
C5 N1 Cu1 N5 -175.7(3) . . . . ?
C1 N1 Cu1 O3 -94.2(4) . . . . ?
C5 N1 Cu1 O3 88.9(3) . . . . ?
C1 N1 Cu1 N2 178.9(4) . . . . ?
C5 N1 Cu1 N2 2.0(3) . . . . ?
C1 N1 Cu1 S1 89.1(4) . . . . ?
C5 N1 Cu1 S1 -87.8(3) . . . . ?
C18 S1 Cu1 N5 5.84(19) . . . . ?
C18 S1 Cu1 O3 89.8(4) . . . . ?
C18 S1 Cu1 N2 -178.29(19) . . . . ?
C18 S1 Cu1 N1 -101.51(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.916
_diffrn_reflns_theta_full        31.18
_diffrn_measured_fraction_theta_full 0.916
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.136
# start Validation Reply Form
_vrf_PLAT029_shelxl              
;
RESPONSE: This Alert is due to the measurement of
 low quality crystals by X-ray diffraction analysis.
;
_vrf_PLAT306_shelxl              
;
RESPONSE: This Alert is due to protons of 
lattice water molecules
could not be located from difference Fourier.
;
_vrf_PLAT430_shelxl              
;
RESPONSE: This Alert is because of oxygen atoms 
of lattice water
molecules are highly disordered and thermal vibrations are
more and thermal parameters are high. 
;
_vrf_PLAT041_shelxl              
;
RESPONSE: This Alert is because protons of lattice water
molecules could not be located from difference Fourier.
;
_vrf_PLAT043_shelxl              
;
RESPONSE: This Alert is because protons of lattice water
molecules could not be located from difference Fourier.
;
_vrf_PLAT068_shelxl              
;
RESPONSE: This Alert is because protons of lattce water
molecules could not be located from difference Fourier.
;
####################################################################### 
# 
# 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_jpl-89
_audit_block_doi                 10.5517/cc13ht6m
_database_code_depnum_ccdc_archive 'CCDC 1028090'
_audit_update_record             
;
2015-01-15 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;
_audit_creation_date             2014-02-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2012-9
_chemical_name_common            ?
_chemical_name_systematic        'Compound 6'
_chemical_formula_moiety         'C22 H18 Cu N6 O3 S'
_chemical_formula_sum            'C22 H18 Cu N6 O3 S'
_chemical_formula_weight         510.02
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H26 N6 S O3 Cu'
_chemical_oxdiff_usercomment     "Lobana's JPL-89"
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.9073(4)
_cell_length_b                   11.5507(6)
_cell_length_c                   14.2629(8)
_cell_angle_alpha                104.034(5)
_cell_angle_beta                 104.217(5)
_cell_angle_gamma                100.871(5)
_cell_volume                     1181.69(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3286
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.4630
_cell_measurement_theta_min      4.0880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.434
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             522
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7648
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.944
_diffrn_reflns_theta_min         3.355
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0416
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0000816000
_diffrn_orient_matrix_UB_12      -0.1168386000
_diffrn_orient_matrix_UB_13      -0.0798962000
_diffrn_orient_matrix_UB_21      -0.0158326000
_diffrn_orient_matrix_UB_22      0.0694086000
_diffrn_orient_matrix_UB_23      -0.0800425000
_diffrn_orient_matrix_UB_31      0.2077660000
_diffrn_orient_matrix_UB_32      0.0429606000
_diffrn_orient_matrix_UB_33      0.0297292000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3830
_reflns_number_total             4471
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0707P)²+0.8792P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1422
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C4(H4), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.19795(6) 0.23405(4) 0.13963(3) 0.02965(16) Uani 1 1 d . . . . .
S1 S 0.37581(10) 0.13249(7) 0.06718(6) 0.0335(2) Uani 1 1 d . . . . .
O1 O 0.0045(3) 0.2760(2) 0.19090(17) 0.0378(5) Uani 1 1 d . . . . .
O2 O 0.0485(4) 0.3291(4) 0.6416(2) 0.0703(10) Uani 1 1 d . . . . .
O3 O -0.1974(4) 0.3818(3) 0.5921(2) 0.0610(8) Uani 1 1 d . . . . .
N1 N 0.3113(3) 0.1927(2) 0.26173(19) 0.0292(5) Uani 1 1 d . . . . .
N2 N 0.4442(3) 0.1293(2) 0.2635(2) 0.0317(5) Uani 1 1 d . . . . .
N3 N 0.6079(4) 0.0373(3) 0.1725(2) 0.0369(6) Uani 1 1 d . . . . .
H3 H 0.6324 0.0153 0.1148 0.044 Uiso 1 1 calc R . . . .
N4 N 0.3442(4) 0.4315(2) 0.1502(2) 0.0324(5) Uani 1 1 d . . . . .
N5 N 0.0634(3) 0.2528(2) 0.00616(19) 0.0288(5) Uani 1 1 d . . . . .
N6 N -0.0656(4) 0.3485(3) 0.5759(2) 0.0470(7) Uani 1 1 d . . . . .
C1 C 0.4815(4) 0.0996(3) 0.1776(2) 0.0304(6) Uani 1 1 d . . . . .
C2 C 0.2716(4) 0.2200(3) 0.3453(2) 0.0329(6) Uani 1 1 d . . . . .
H2 H 0.3457 0.2043 0.4017 0.039 Uiso 1 1 calc R . . . .
C3 C 0.1252(4) 0.2724(3) 0.3616(2) 0.0323(6) Uani 1 1 d . . . . .
C4 C 0.1024(4) 0.2929(3) 0.4573(2) 0.0371(7) Uani 1 1 d . . . . .
H4 H 0.1878 0.2790 0.5103 0.044 Uiso 1 1 calc R . . . .
C5 C -0.0436(4) 0.3332(3) 0.4762(2) 0.0363(7) Uani 1 1 d . . . . .
C6 C -0.1709(4) 0.3546(3) 0.4007(3) 0.0364(7) Uani 1 1 d . . . . .
H6 H -0.2710 0.3816 0.4145 0.044 Uiso 1 1 calc R . . . .
C7 C -0.1506(4) 0.3363(3) 0.3063(3) 0.0350(7) Uani 1 1 d . . . . .
H7 H -0.2374 0.3519 0.2550 0.042 Uiso 1 1 calc R . . . .
C8 C -0.0033(4) 0.2946(3) 0.2823(2) 0.0312(6) Uani 1 1 d . . . . .
C9 C 0.7053(4) 0.0048(3) 0.2583(3) 0.0373(7) Uani 1 1 d . . . . .
H9A H 0.6216 -0.0579 0.2738 0.045 Uiso 1 1 calc R . . . .
H9B H 0.7549 0.0790 0.3187 0.045 Uiso 1 1 calc R . . . .
C10 C 0.8584(5) -0.0463(3) 0.2346(3) 0.0448(8) Uani 1 1 d . . . . .
H10A H 0.8082 -0.1244 0.1793 0.067 Uiso 1 1 calc GR . . . .
H10B H 0.9301 -0.0608 0.2952 0.067 Uiso 1 1 calc GR . . . .
H10C H 0.9357 0.0133 0.2141 0.067 Uiso 1 1 calc GR . . . .
C11 C 0.2742(4) 0.4535(3) 0.0612(2) 0.0277(6) Uani 1 1 d . . . . .
C12 C 0.1241(4) 0.3590(3) -0.0145(2) 0.0268(6) Uani 1 1 d . . . . .
C13 C -0.0787(4) 0.1677(3) -0.0611(3) 0.0339(6) Uani 1 1 d . . . . .
H13 H -0.1214 0.0940 -0.0459 0.041 Uiso 1 1 calc R . . . .
C14 C -0.1691(4) 0.1813(3) -0.1538(3) 0.0366(7) Uani 1 1 d . . . . .
H14 H -0.2710 0.1181 -0.2002 0.044 Uiso 1 1 calc R . . . .
C15 C -0.1086(4) 0.2865(3) -0.1763(2) 0.0335(6) Uani 1 1 d . . . . .
H15 H -0.1673 0.2969 -0.2392 0.040 Uiso 1 1 calc R . . . .
C16 C 0.0410(4) 0.3796(3) -0.1061(2) 0.0301(6) Uani 1 1 d . . . . .
C17 C 0.1091(4) 0.4939(3) -0.1232(2) 0.0344(7) Uani 1 1 d . . . . .
H17 H 0.0530 0.5084 -0.1847 0.041 Uiso 1 1 calc R . . . .
C18 C 0.2522(5) 0.5817(3) -0.0529(3) 0.0357(7) Uani 1 1 d . . . . .
H18 H 0.2953 0.6569 -0.0660 0.043 Uiso 1 1 calc R . . . .
C19 C 0.3393(4) 0.5633(3) 0.0404(2) 0.0314(6) Uani 1 1 d . . . . .
C20 C 0.4850(4) 0.6532(3) 0.1163(3) 0.0386(7) Uani 1 1 d . . . . .
H20 H 0.5337 0.7291 0.1059 0.046 Uiso 1 1 calc R . . . .
C21 C 0.5562(5) 0.6304(3) 0.2057(3) 0.0425(8) Uani 1 1 d . . . . .
H21 H 0.6555 0.6900 0.2577 0.051 Uiso 1 1 calc R . . . .
C22 C 0.4810(5) 0.5187(3) 0.2193(3) 0.0398(7) Uani 1 1 d . . . . .
H22 H 0.5311 0.5046 0.2819 0.048 Uiso 1 1 calc R . . . .


_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 S1 2.2737(8) . ?
Cu1 O1 1.940(2) . ?
Cu1 N1 1.965(3) . ?
Cu1 N4 2.306(3) . ?
Cu1 N5 2.024(3) . ?
S1 C1 1.757(3) . ?
O1 C8 1.288(4) . ?
O2 N6 1.226(4) . ?
O3 N6 1.230(4) . ?
N1 N2 1.389(4) . ?
N1 C2 1.288(4) . ?
N2 C1 1.310(4) . ?
N3 H3 0.8800 . ?
N3 C1 1.343(4) . ?
N3 C9 1.450(4) . ?
N4 C11 1.359(4) . ?
N4 C22 1.319(4) . ?
N5 C12 1.358(4) . ?
N5 C13 1.321(4) . ?
N6 C5 1.448(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.444(4) . ?
C3 C4 1.391(4) . ?
C3 C8 1.432(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(5) . ?
C5 C6 1.387(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.365(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.427(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.517(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.440(4) . ?
C11 C19 1.405(4) . ?
C12 C16 1.409(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.400(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.362(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.406(5) . ?
C16 C17 1.430(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.353(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.426(5) . ?
C19 C20 1.403(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.370(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.395(5) . ?
C22 H22 0.9500 . ?

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
S1 Cu1 N4 97.65(7) . . ?
O1 Cu1 S1 164.56(8) . . ?
O1 Cu1 N1 92.62(10) . . ?
O1 Cu1 N4 97.39(10) . . ?
O1 Cu1 N5 87.64(9) . . ?
N1 Cu1 S1 85.54(8) . . ?
N1 Cu1 N4 109.94(10) . . ?
N1 Cu1 N5 172.46(10) . . ?
N5 Cu1 S1 92.20(7) . . ?
N5 Cu1 N4 77.47(10) . . ?
C1 S1 Cu1 94.30(10) . . ?
C8 O1 Cu1 127.7(2) . . ?
N2 N1 Cu1 121.13(19) . . ?
C2 N1 Cu1 124.7(2) . . ?
C2 N1 N2 114.2(3) . . ?
C1 N2 N1 113.9(3) . . ?
C1 N3 H3 118.7 . . ?
C1 N3 C9 122.5(3) . . ?
C9 N3 H3 118.7 . . ?
C11 N4 Cu1 108.67(19) . . ?
C22 N4 Cu1 133.9(2) . . ?
C22 N4 C11 117.3(3) . . ?
C12 N5 Cu1 117.5(2) . . ?
C13 N5 Cu1 123.6(2) . . ?
C13 N5 C12 118.9(3) . . ?
O2 N6 O3 122.3(3) . . ?
O2 N6 C5 118.9(3) . . ?
O3 N6 C5 118.7(3) . . ?
N2 C1 S1 125.1(2) . . ?
N2 C1 N3 117.8(3) . . ?
N3 C1 S1 117.1(2) . . ?
N1 C2 H2 116.9 . . ?
N1 C2 C3 126.2(3) . . ?
C3 C2 H2 116.9 . . ?
C4 C3 C2 117.4(3) . . ?
C4 C3 C8 119.3(3) . . ?
C8 C3 C2 123.1(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 N6 118.7(3) . . ?
C4 C5 C6 121.2(3) . . ?
C6 C5 N6 120.0(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.2(3) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 119.0 . . ?
C6 C7 C8 122.0(3) . . ?
C8 C7 H7 119.0 . . ?
O1 C8 C3 123.8(3) . . ?
O1 C8 C7 118.7(3) . . ?
C7 C8 C3 117.5(3) . . ?
N3 C9 H9A 109.6 . . ?
N3 C9 H9B 109.6 . . ?
N3 C9 C10 110.1(3) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C11 C12 117.6(3) . . ?
N4 C11 C19 123.4(3) . . ?
C19 C11 C12 119.0(3) . . ?
N5 C12 C11 118.5(3) . . ?
N5 C12 C16 121.7(3) . . ?
C16 C12 C11 119.8(3) . . ?
N5 C13 H13 118.5 . . ?
N5 C13 C14 122.9(3) . . ?
C14 C13 H13 118.5 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C12 C16 C17 119.3(3) . . ?
C15 C16 C12 117.8(3) . . ?
C15 C16 C17 122.9(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.1(3) . . ?
C19 C18 H18 119.4 . . ?
C11 C19 C18 119.8(3) . . ?
C20 C19 C11 117.2(3) . . ?
C20 C19 C18 122.9(3) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 C19 119.3(3) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.1(3) . . ?
C22 C21 H21 120.4 . . ?
N4 C22 C21 123.7(3) . . ?
N4 C22 H22 118.1 . . ?
C21 C22 H22 118.1 . . ?

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
C17 H17 O1 0.95 2.63 3.244(4) 122.5 2_565
C21 H21 O2 0.95 2.51 3.216(5) 131.5 2_666

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
Cu1 S1 C1 N2 1.9(3) . . . . ?
Cu1 S1 C1 N3 -179.4(2) . . . . ?
Cu1 O1 C8 C3 -7.9(5) . . . . ?
Cu1 O1 C8 C7 174.0(2) . . . . ?
Cu1 N1 N2 C1 -1.1(3) . . . . ?
Cu1 N1 C2 C3 7.5(5) . . . . ?
Cu1 N4 C11 C12 4.0(3) . . . . ?
Cu1 N4 C11 C19 -176.8(2) . . . . ?
Cu1 N4 C22 C21 175.1(2) . . . . ?
Cu1 N5 C12 C11 -2.7(3) . . . . ?
Cu1 N5 C12 C16 179.0(2) . . . . ?
Cu1 N5 C13 C14 -179.2(2) . . . . ?
O2 N6 C5 C4 2.3(5) . . . . ?
O2 N6 C5 C6 180.0(4) . . . . ?
O3 N6 C5 C4 -178.4(3) . . . . ?
O3 N6 C5 C6 -0.8(5) . . . . ?
N1 N2 C1 S1 -0.8(4) . . . . ?
N1 N2 C1 N3 -179.6(3) . . . . ?
N1 C2 C3 C4 178.7(3) . . . . ?
N1 C2 C3 C8 3.6(5) . . . . ?
N2 N1 C2 C3 -172.3(3) . . . . ?
N4 C11 C12 N5 -1.3(4) . . . . ?
N4 C11 C12 C16 177.0(2) . . . . ?
N4 C11 C19 C18 -176.8(3) . . . . ?
N4 C11 C19 C20 0.4(4) . . . . ?
N5 C12 C16 C15 0.3(4) . . . . ?
N5 C12 C16 C17 179.1(3) . . . . ?
N5 C13 C14 C15 0.2(5) . . . . ?
N6 C5 C6 C7 -178.2(3) . . . . ?
C1 N3 C9 C10 -171.0(3) . . . . ?
C2 N1 N2 C1 178.8(3) . . . . ?
C2 C3 C4 C5 -174.7(3) . . . . ?
C2 C3 C8 O1 -3.6(5) . . . . ?
C2 C3 C8 C7 174.6(3) . . . . ?
C3 C4 C5 N6 177.6(3) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C3 C8 O1 -178.6(3) . . . . ?
C4 C3 C8 C7 -0.4(4) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
C5 C6 C7 C8 0.7(5) . . . . ?
C6 C7 C8 O1 178.1(3) . . . . ?
C6 C7 C8 C3 -0.2(5) . . . . ?
C8 C3 C4 C5 0.6(5) . . . . ?
C9 N3 C1 S1 179.8(2) . . . . ?
C9 N3 C1 N2 -1.4(5) . . . . ?
C11 N4 C22 C21 -0.1(5) . . . . ?
C11 C12 C16 C15 -178.0(3) . . . . ?
C11 C12 C16 C17 0.8(4) . . . . ?
C11 C19 C20 C21 0.1(4) . . . . ?
C12 N5 C13 C14 0.7(4) . . . . ?
C12 C11 C19 C18 2.4(4) . . . . ?
C12 C11 C19 C20 179.6(3) . . . . ?
C12 C16 C17 C18 0.4(4) . . . . ?
C13 N5 C12 C11 177.4(3) . . . . ?
C13 N5 C12 C16 -0.9(4) . . . . ?
C13 C14 C15 C16 -0.8(5) . . . . ?
C14 C15 C16 C12 0.6(4) . . . . ?
C14 C15 C16 C17 -178.2(3) . . . . ?
C15 C16 C17 C18 179.2(3) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C11 -1.2(4) . . . . ?
C17 C18 C19 C20 -178.3(3) . . . . ?
C18 C19 C20 C21 177.2(3) . . . . ?
C19 C11 C12 N5 179.4(2) . . . . ?
C19 C11 C12 C16 -2.2(4) . . . . ?
C19 C20 C21 C22 -0.5(5) . . . . ?
C20 C21 C22 N4 0.6(5) . . . . ?
C22 N4 C11 C12 -179.6(3) . . . . ?
C22 N4 C11 C19 -0.4(4) . . . . ?

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1028106'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Cu N6 O3 S'
_chemical_formula_sum            'C24 H18 Cu N6 O3 S'
_chemical_formula_weight         534.06

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8808(6)
_cell_length_b                   10.9146(9)
_cell_length_c                   14.0860(9)
_cell_angle_alpha                99.182(3)
_cell_angle_beta                 94.515(3)
_cell_angle_gamma                102.572(3)
_cell_volume                     1159.29(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8526
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.50

_exptl_crystal_description       Prism
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             546
_exptl_absorpt_coefficient_mu    1.072
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19878
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         27.71
_reflns_number_total             5358
_reflns_number_gt                4400
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
There is only one restraint used during structure refinement i.e. DFIX. 
DFIX is used to fix distance of proton
 of -NH group to its N atom.
 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0545P)²+0.3410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5358
_refine_ls_number_parameters     319
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1060(3) -0.0183(2) 0.29252(17) 0.0508(5) Uani 1 1 d . . .
H1 H 0.0969 0.0093 0.2336 0.061 Uiso 1 1 calc R . .
C2 C 0.0044(3) -0.1359(3) 0.3002(2) 0.0633(7) Uani 1 1 d . . .
H2 H -0.0712 -0.1867 0.2477 0.076 Uiso 1 1 calc R . .
C3 C 0.0185(4) -0.1753(2) 0.3870(2) 0.0676(7) Uani 1 1 d . . .
H3 H -0.0499 -0.2533 0.3947 0.081 Uiso 1 1 calc R . .
C4 C 0.1332(3) -0.1001(2) 0.46300(18) 0.0562(6) Uani 1 1 d . . .
H4 H 0.1451 -0.1268 0.5221 0.067 Uiso 1 1 calc R . .
C5 C 0.2310(3) 0.01660(19) 0.44979(15) 0.0402(4) Uani 1 1 d . . .
C6 C 0.3603(3) 0.1041(2) 0.52672(14) 0.0404(4) Uani 1 1 d . . .
C7 C 0.4074(3) 0.0716(3) 0.61485(17) 0.0568(6) Uani 1 1 d . . .
H7 H 0.3559 -0.0078 0.6285 0.068 Uiso 1 1 calc R . .
C8 C 0.5303(4) 0.1576(3) 0.68165(17) 0.0672(8) Uani 1 1 d . . .
H8 H 0.5614 0.1372 0.7413 0.081 Uiso 1 1 calc R . .
C9 C 0.6063(4) 0.2722(3) 0.66032(19) 0.0675(7) Uani 1 1 d . . .
H9 H 0.6908 0.3309 0.7047 0.081 Uiso 1 1 calc R . .
C10 C 0.5566(3) 0.3006(3) 0.57210(17) 0.0559(6) Uani 1 1 d . . .
H10 H 0.6090 0.3791 0.5574 0.067 Uiso 1 1 calc R . .
C11 C 0.6151(3) 0.19766(19) 0.24566(14) 0.0404(4) Uani 1 1 d . . .
C12 C 0.7649(3) 0.1505(2) 0.22558(16) 0.0496(5) Uani 1 1 d . . .
H12 H 0.8369 0.1382 0.2770 0.059 Uiso 1 1 calc R . .
C13 C 0.8078(3) 0.1226(3) 0.13453(17) 0.0610(7) Uani 1 1 d . . .
H13 H 0.9061 0.0905 0.1239 0.073 Uiso 1 1 calc R . .
C14 C 0.7027(4) 0.1427(3) 0.05781(17) 0.0706(8) Uani 1 1 d . . .
C15 C 0.5570(4) 0.1888(3) 0.07216(17) 0.0665(7) Uani 1 1 d . . .
H15 H 0.4894 0.2021 0.0193 0.080 Uiso 1 1 calc R . .
C16 C 0.5085(3) 0.2162(2) 0.16445(15) 0.0462(5) Uani 1 1 d . . .
C17 C 0.3617(3) 0.2737(2) 0.17443(15) 0.0473(5) Uani 1 1 d . . .
H17 H 0.3065 0.2887 0.1180 0.057 Uiso 1 1 calc R . .
C18 C 0.1036(3) 0.4027(2) 0.32327(15) 0.0427(4) Uani 1 1 d . . .
C19 C -0.1164(3) 0.5026(2) 0.24441(17) 0.0500(5) Uani 1 1 d . . .
C20 C -0.2790(3) 0.5272(2) 0.2567(2) 0.0575(6) Uani 1 1 d . . .
H20 H -0.3269 0.5172 0.3141 0.069 Uiso 1 1 calc R . .
C21 C -0.3709(4) 0.5666(3) 0.1840(2) 0.0699(8) Uani 1 1 d . . .
H21 H -0.4809 0.5815 0.1924 0.084 Uiso 1 1 calc R . .
C22 C -0.3017(5) 0.5836(3) 0.1006(2) 0.0852(10) Uani 1 1 d . . .
H22 H -0.3644 0.6092 0.0516 0.102 Uiso 1 1 calc R . .
C23 C -0.1387(5) 0.5628(4) 0.0890(2) 0.0982(13) Uani 1 1 d . . .
H23 H -0.0905 0.5761 0.0323 0.118 Uiso 1 1 calc R . .
C24 C -0.0444(4) 0.5224(3) 0.1601(2) 0.0762(9) Uani 1 1 d . . .
H24 H 0.0662 0.5088 0.1513 0.091 Uiso 1 1 calc R . .
N1 N 0.2159(2) 0.05711(16) 0.36554(12) 0.0403(4) Uani 1 1 d . . .
N2 N 0.4346(2) 0.21823(17) 0.50662(12) 0.0408(4) Uani 1 1 d . . .
N3 N 0.7521(4) 0.1176(4) -0.03892(17) 0.1160(13) Uani 1 1 d . . .
N4 N 0.2995(2) 0.30638(16) 0.25359(12) 0.0405(4) Uani 1 1 d . . .
N5 N 0.1676(2) 0.37185(18) 0.24325(13) 0.0456(4) Uani 1 1 d . . .
N6 N -0.0288(3) 0.4662(2) 0.32251(14) 0.0519(5) Uani 1 1 d D . .
H6A H -0.076(3) 0.470(3) 0.3738(15) 0.062 Uiso 1 1 d D . .
O1 O 0.58316(19) 0.22263(16) 0.33402(10) 0.0484(4) Uani 1 1 d . . .
O2 O 0.8761(5) 0.0723(4) -0.05153(17) 0.176(2) Uani 1 1 d . . .
O3 O 0.6649(5) 0.1419(4) -0.10469(16) 0.177(2) Uani 1 1 d . . .
S1 S 0.17040(8) 0.37068(6) 0.43607(4) 0.05195(15) Uani 1 1 d . . .
Cu1 Cu 0.36599(3) 0.25932(2) 0.376790(16) 0.03909(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.328(3) . ?
C1 C2 1.383(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.337(3) . ?
C5 C6 1.482(3) . ?
C6 N2 1.340(3) . ?
C6 C7 1.389(3) . ?
C7 C8 1.372(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.355(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(4) . ?
C9 H9 0.9300 . ?
C10 N2 1.342(3) . ?
C10 H10 0.9300 . ?
C11 O1 1.288(2) . ?
C11 C12 1.417(3) . ?
C11 C16 1.433(3) . ?
C12 C13 1.357(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(3) . ?
C14 N3 1.447(3) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.437(3) . ?
C17 N4 1.283(3) . ?
C17 H17 0.9300 . ?
C18 N5 1.296(3) . ?
C18 N6 1.372(3) . ?
C18 S1 1.746(2) . ?
C19 C24 1.383(4) . ?
C19 C20 1.384(3) . ?
C19 N6 1.409(3) . ?
C20 C21 1.385(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.356(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
N1 Cu1 2.2400(17) . ?
N2 Cu1 2.0125(17) . ?
N3 O2 1.200(3) . ?
N3 O3 1.208(3) . ?
N4 N5 1.395(2) . ?
N4 Cu1 1.9515(16) . ?
N6 H6A 0.838(17) . ?
O1 Cu1 1.9586(14) . ?
S1 Cu1 2.2902(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.9(2) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 118.6(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 121.8(2) . . ?
N1 C5 C6 115.35(17) . . ?
C4 C5 C6 122.88(19) . . ?
N2 C6 C7 120.4(2) . . ?
N2 C6 C5 116.38(17) . . ?
C7 C6 C5 123.2(2) . . ?
C8 C7 C6 119.5(2) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
N2 C10 C9 122.0(3) . . ?
N2 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
O1 C11 C12 119.37(17) . . ?
O1 C11 C16 123.82(18) . . ?
C12 C11 C16 116.81(18) . . ?
C13 C12 C11 122.9(2) . . ?
C13 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
C12 C13 C14 118.8(2) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C15 C14 C13 121.3(2) . . ?
C15 C14 N3 119.8(2) . . ?
C13 C14 N3 118.8(2) . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C11 119.15(19) . . ?
C15 C16 C17 117.64(19) . . ?
C11 C16 C17 122.93(19) . . ?
N4 C17 C16 126.32(19) . . ?
N4 C17 H17 116.8 . . ?
C16 C17 H17 116.8 . . ?
N5 C18 N6 119.19(19) . . ?
N5 C18 S1 125.82(16) . . ?
N6 C18 S1 114.99(16) . . ?
C24 C19 C20 119.1(2) . . ?
C24 C19 N6 123.7(2) . . ?
C20 C19 N6 117.1(2) . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 120.6(3) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.4(3) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C22 C23 C24 121.3(3) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C19 C24 C23 119.3(3) . . ?
C19 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C1 N1 C5 118.53(19) . . ?
C1 N1 Cu1 129.34(15) . . ?
C5 N1 Cu1 111.75(14) . . ?
C6 N2 C10 119.38(19) . . ?
C6 N2 Cu1 118.94(14) . . ?
C10 N2 Cu1 121.65(16) . . ?
O2 N3 O3 122.2(3) . . ?
O2 N3 C14 119.4(2) . . ?
O3 N3 C14 118.4(2) . . ?
C17 N4 N5 113.94(17) . . ?
C17 N4 Cu1 124.35(14) . . ?
N5 N4 Cu1 121.54(13) . . ?
C18 N5 N4 113.51(17) . . ?
C18 N6 C19 129.63(19) . . ?
C18 N6 H6A 113.6(18) . . ?
C19 N6 H6A 115.6(18) . . ?
C11 O1 Cu1 126.15(13) . . ?
C18 S1 Cu1 93.86(7) . . ?
N4 Cu1 O1 92.20(6) . . ?
N4 Cu1 N2 177.60(7) . . ?
O1 Cu1 N2 88.97(6) . . ?
N4 Cu1 N1 104.91(7) . . ?
O1 Cu1 N1 97.64(6) . . ?
N2 Cu1 N1 77.00(7) . . ?
N4 Cu1 S1 85.05(5) . . ?
O1 Cu1 S1 160.58(5) . . ?
N2 Cu1 S1 93.16(5) . . ?
N1 Cu1 S1 101.65(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
N1 C1 C2 C3 0.2(4) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 N1 0.1(3) . . . . ?
C3 C4 C5 C6 -179.1(2) . . . . ?
N1 C5 C6 N2 6.2(2) . . . . ?
C4 C5 C6 N2 -174.56(19) . . . . ?
N1 C5 C6 C7 -172.59(18) . . . . ?
C4 C5 C6 C7 6.7(3) . . . . ?
N2 C6 C7 C8 0.3(3) . . . . ?
C5 C6 C7 C8 179.0(2) . . . . ?
C6 C7 C8 C9 -1.0(4) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C8 C9 C10 N2 0.2(4) . . . . ?
O1 C11 C12 C13 -179.7(2) . . . . ?
C16 C11 C12 C13 -0.5(4) . . . . ?
C11 C12 C13 C14 1.1(4) . . . . ?
C12 C13 C14 C15 -0.6(5) . . . . ?
C12 C13 C14 N3 177.7(3) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
N3 C14 C15 C16 -178.7(3) . . . . ?
C14 C15 C16 C11 1.1(4) . . . . ?
C14 C15 C16 C17 175.2(3) . . . . ?
O1 C11 C16 C15 178.6(2) . . . . ?
C12 C11 C16 C15 -0.6(3) . . . . ?
O1 C11 C16 C17 4.8(4) . . . . ?
C12 C11 C16 C17 -174.4(2) . . . . ?
C15 C16 C17 N4 -179.4(2) . . . . ?
C11 C16 C17 N4 -5.5(4) . . . . ?
C24 C19 C20 C21 2.4(4) . . . . ?
N6 C19 C20 C21 178.3(2) . . . . ?
C19 C20 C21 C22 -1.1(4) . . . . ?
C20 C21 C22 C23 -0.7(5) . . . . ?
C21 C22 C23 C24 1.2(6) . . . . ?
C20 C19 C24 C23 -1.9(5) . . . . ?
N6 C19 C24 C23 -177.5(3) . . . . ?
C22 C23 C24 C19 0.1(6) . . . . ?
C2 C1 N1 C5 1.0(3) . . . . ?
C2 C1 N1 Cu1 -171.18(17) . . . . ?
C4 C5 N1 C1 -1.2(3) . . . . ?
C6 C5 N1 C1 178.10(17) . . . . ?
C4 C5 N1 Cu1 172.35(16) . . . . ?
C6 C5 N1 Cu1 -8.4(2) . . . . ?
C7 C6 N2 C10 0.7(3) . . . . ?
C5 C6 N2 C10 -178.09(18) . . . . ?
C7 C6 N2 Cu1 178.66(15) . . . . ?
C5 C6 N2 Cu1 -0.1(2) . . . . ?
C9 C10 N2 C6 -0.9(3) . . . . ?
C9 C10 N2 Cu1 -178.86(18) . . . . ?
C15 C14 N3 O2 -177.0(4) . . . . ?
C13 C14 N3 O2 4.8(6) . . . . ?
C15 C14 N3 O3 2.2(6) . . . . ?
C13 C14 N3 O3 -176.1(4) . . . . ?
C16 C17 N4 N5 173.8(2) . . . . ?
C16 C17 N4 Cu1 -10.8(3) . . . . ?
N6 C18 N5 N4 -179.22(18) . . . . ?
S1 C18 N5 N4 0.8(3) . . . . ?
C17 N4 N5 C18 178.94(19) . . . . ?
Cu1 N4 N5 C18 3.4(2) . . . . ?
N5 C18 N6 C19 2.3(4) . . . . ?
S1 C18 N6 C19 -177.6(2) . . . . ?
C24 C19 N6 C18 -24.9(4) . . . . ?
C20 C19 N6 C18 159.3(2) . . . . ?
C12 C11 O1 Cu1 -168.60(16) . . . . ?
C16 C11 O1 Cu1 12.2(3) . . . . ?
N5 C18 S1 Cu1 -3.5(2) . . . . ?
N6 C18 S1 Cu1 176.52(16) . . . . ?
C17 N4 Cu1 O1 19.71(19) . . . . ?
N5 N4 Cu1 O1 -165.27(15) . . . . ?
C17 N4 Cu1 N1 -78.79(19) . . . . ?
N5 N4 Cu1 N1 96.22(15) . . . . ?
C17 N4 Cu1 S1 -179.55(19) . . . . ?
N5 N4 Cu1 S1 -4.53(14) . . . . ?
C11 O1 Cu1 N4 -20.82(18) . . . . ?
C11 O1 Cu1 N2 161.27(18) . . . . ?
C11 O1 Cu1 N1 84.54(17) . . . . ?
C11 O1 Cu1 S1 -102.1(2) . . . . ?
C6 N2 Cu1 O1 -101.35(15) . . . . ?
C10 N2 Cu1 O1 76.57(17) . . . . ?
C6 N2 Cu1 N1 -3.27(14) . . . . ?
C10 N2 Cu1 N1 174.65(18) . . . . ?
C6 N2 Cu1 S1 97.97(14) . . . . ?
C10 N2 Cu1 S1 -84.11(17) . . . . ?
C1 N1 Cu1 N4 0.59(19) . . . . ?
C5 N1 Cu1 N4 -172.06(13) . . . . ?
C1 N1 Cu1 O1 -93.75(18) . . . . ?
C5 N1 Cu1 O1 93.60(13) . . . . ?
C1 N1 Cu1 N2 179.09(19) . . . . ?
C5 N1 Cu1 N2 6.44(13) . . . . ?
C1 N1 Cu1 S1 88.51(18) . . . . ?
C5 N1 Cu1 S1 -84.14(13) . . . . ?
C18 S1 Cu1 N4 3.51(9) . . . . ?
C18 S1 Cu1 O1 86.04(15) . . . . ?
C18 S1 Cu1 N2 -178.09(9) . . . . ?
C18 S1 Cu1 N1 -100.72(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.71
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1028108'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18 Cu N6 O3 S'
_chemical_formula_sum            'C26 H18 Cu N6 O3 S'
_chemical_formula_weight         558.08

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7532(6)
_cell_length_b                   12.0716(9)
_cell_length_c                   14.2178(9)
_cell_angle_alpha                103.320(4)
_cell_angle_beta                 99.041(4)
_cell_angle_gamma                105.263(4)
_cell_volume                     1215.14(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4794
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      25.19


_exptl_crystal_description       Prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             570
_exptl_absorpt_coefficient_mu    1.027
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
'SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18860
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         26.40
_reflns_number_total             4963
_reflns_number_gt                3854
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
There is only one restraint used during structure refinement i.e. DFIX. 
DFIX is used to fix distance of proton
 of -NH group to its N atom.  

 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0484P)²+0.6629P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4963
_refine_ls_number_parameters     337
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4253(5) 0.6894(3) 0.4390(2) 0.0552(8) Uani 1 1 d . . .
H1 H 0.3712 0.6141 0.4459 0.066 Uiso 1 1 calc R . .
C2 C 0.3545(5) 0.7171(4) 0.3556(2) 0.0696(11) Uani 1 1 d . . .
H2 H 0.2528 0.6623 0.3083 0.084 Uiso 1 1 calc R . .
C3 C 0.4334(6) 0.8234(4) 0.3434(2) 0.0680(11) Uani 1 1 d . . .
H3 H 0.3879 0.8419 0.2864 0.082 Uiso 1 1 calc R . .
C4 C 0.5840(5) 0.9079(3) 0.4152(3) 0.0589(10) Uani 1 1 d . . .
C5 C 0.6723(7) 1.0226(4) 0.4092(4) 0.0815(14) Uani 1 1 d . . .
H5 H 0.6312 1.0452 0.3537 0.098 Uiso 1 1 calc R . .
C6 C 0.8130(7) 1.1001(4) 0.4805(4) 0.0826(15) Uani 1 1 d . . .
H6 H 0.8706 1.1742 0.4726 0.099 Uiso 1 1 calc R . .
C7 C 0.8778(5) 1.0709(3) 0.5700(3) 0.0667(11) Uani 1 1 d . . .
C8 C 1.0141(6) 1.1487(4) 0.6505(5) 0.0949(17) Uani 1 1 d . . .
H8 H 1.0742 1.2251 0.6479 0.114 Uiso 1 1 calc R . .
C9 C 1.0618(6) 1.1155(4) 0.7333(4) 0.0913(16) Uani 1 1 d . . .
H9 H 1.1556 1.1679 0.7864 0.110 Uiso 1 1 calc R . .
C10 C 0.9667(5) 1.0001(3) 0.7377(3) 0.0690(11) Uani 1 1 d . . .
H10 H 0.9972 0.9784 0.7953 0.083 Uiso 1 1 calc R . .
C11 C 0.7914(4) 0.9573(3) 0.5805(2) 0.0450(7) Uani 1 1 d . . .
C12 C 0.6464(4) 0.8745(3) 0.5008(2) 0.0414(7) Uani 1 1 d . . .
C13 C 1.1000(5) 0.4937(4) 0.8314(3) 0.0690(11) Uani 1 1 d . . .
H13 H 0.9967 0.5133 0.8452 0.083 Uiso 1 1 calc R . .
C14 C 1.2051(6) 0.4559(4) 0.8984(3) 0.0816(13) Uani 1 1 d . . .
H14 H 1.1708 0.4503 0.9574 0.098 Uiso 1 1 calc R . .
C15 C 1.3563(6) 0.4269(3) 0.8798(3) 0.0751(12) Uani 1 1 d . . .
H15 H 1.4246 0.4016 0.9255 0.090 Uiso 1 1 calc R . .
C16 C 1.4075(5) 0.4352(3) 0.7931(3) 0.0681(11) Uani 1 1 d . . .
H16 H 1.5116 0.4159 0.7802 0.082 Uiso 1 1 calc R . .
C17 C 1.3056(4) 0.4719(3) 0.7250(3) 0.0552(8) Uani 1 1 d . . .
H17 H 1.3407 0.4766 0.6660 0.066 Uiso 1 1 calc R . .
C18 C 1.1515(4) 0.5017(3) 0.7437(2) 0.0484(8) Uani 1 1 d . . .
C19 C 0.9263(4) 0.5953(3) 0.6743(2) 0.0414(7) Uani 1 1 d . . .
C20 C 0.7011(4) 0.7152(3) 0.8367(2) 0.0462(7) Uani 1 1 d . . .
H20 H 0.7635 0.6996 0.8911 0.055 Uiso 1 1 calc R . .
C21 C 0.5618(4) 0.7695(3) 0.8529(2) 0.0459(7) Uani 1 1 d . . .
C22 C 0.5324(6) 0.7960(3) 0.9483(2) 0.0651(10) Uani 1 1 d . . .
H22 H 0.6105 0.7847 0.9995 0.078 Uiso 1 1 calc R . .
C23 C 0.3919(6) 0.8380(4) 0.9685(3) 0.0734(11) Uani 1 1 d . . .
C24 C 0.2719(6) 0.8554(3) 0.8940(3) 0.0680(10) Uani 1 1 d . . .
H24 H 0.1750 0.8831 0.9080 0.082 Uiso 1 1 calc R . .
C25 C 0.2984(5) 0.8313(3) 0.8001(2) 0.0565(9) Uani 1 1 d . . .
H25 H 0.2184 0.8436 0.7505 0.068 Uiso 1 1 calc R . .
C26 C 0.4427(4) 0.7884(3) 0.7752(2) 0.0435(7) Uani 1 1 d . . .
N1 N 0.8367(3) 0.9227(2) 0.66307(19) 0.0458(6) Uani 1 1 d . . .
N2 N 0.5676(3) 0.7655(2) 0.51014(16) 0.0381(5) Uani 1 1 d . . .
N3 N 1.0519(4) 0.5352(3) 0.66899(19) 0.0507(7) Uani 1 1 d D . .
H3A H 1.089(4) 0.531(3) 0.6170(18) 0.061 Uiso 1 1 d D . .
N4 N 0.8764(3) 0.6237(2) 0.75729(17) 0.0446(6) Uani 1 1 d . . .
N5 N 0.7490(3) 0.6856(2) 0.75421(16) 0.0406(6) Uani 1 1 d . . .
N6 N 0.3660(8) 0.8617(5) 1.0692(3) 0.1261(19) Uani 1 1 d . . .
O1 O 0.4580(3) 0.7654(2) 0.68449(14) 0.0512(5) Uani 1 1 d . . .
O2 O 0.4731(8) 0.8447(5) 1.1323(3) 0.183(3) Uani 1 1 d . . .
O3 O 0.2352(7) 0.8957(5) 1.0852(3) 0.163(2) Uani 1 1 d . . .
S1 S 0.84156(11) 0.62512(7) 0.56477(5) 0.0461(2) Uani 1 1 d . . .
Cu1 Cu 0.66338(5) 0.72910(3) 0.63546(2) 0.03685(13) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.331(4) . ?
C1 C2 1.376(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.332(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(5) . ?
C4 C12 1.421(4) . ?
C5 C6 1.330(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.448(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(6) . ?
C7 C11 1.411(4) . ?
C8 C9 1.356(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.415(6) . ?
C9 H9 0.9300 . ?
C10 N1 1.314(4) . ?
C10 H10 0.9300 . ?
C11 N1 1.361(4) . ?
C11 C12 1.426(4) . ?
C12 N2 1.344(4) . ?
C13 C18 1.383(5) . ?
C13 C14 1.391(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.355(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(4) . ?
C17 H17 0.9300 . ?
C18 N3 1.412(4) . ?
C19 N4 1.298(4) . ?
C19 N3 1.360(4) . ?
C19 S1 1.746(3) . ?
C20 N5 1.286(4) . ?
C20 C21 1.425(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.390(4) . ?
C21 C26 1.425(4) . ?
C22 C23 1.360(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.388(5) . ?
C23 N6 1.450(5) . ?
C24 C25 1.358(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.411(4) . ?
C25 H25 0.9300 . ?
C26 O1 1.286(3) . ?
N1 Cu1 2.276(2) . ?
N2 Cu1 2.009(2) . ?
N3 H3A 0.829(18) . ?
N4 N5 1.387(3) . ?
N5 Cu1 1.951(2) . ?
N6 O2 1.217(5) . ?
N6 O3 1.224(5) . ?
O1 Cu1 1.947(2) . ?
S1 Cu1 2.2940(8) . ?

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
N2 C1 C2 122.9(3) . . ?
N2 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 124.6(4) . . ?
C3 C4 C12 116.8(3) . . ?
C5 C4 C12 118.6(4) . . ?
C6 C5 C4 122.1(4) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 121.1(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C11 115.9(4) . . ?
C8 C7 C6 125.0(4) . . ?
C11 C7 C6 119.0(4) . . ?
C9 C8 C7 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 119.1(4) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N1 C10 C9 122.0(4) . . ?
N1 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
N1 C11 C7 123.7(3) . . ?
N1 C11 C12 117.9(2) . . ?
C7 C11 C12 118.4(3) . . ?
N2 C12 C4 121.1(3) . . ?
N2 C12 C11 118.1(2) . . ?
C4 C12 C11 120.7(3) . . ?
C18 C13 C14 119.0(4) . . ?
C18 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 121.6(4) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C16 119.4(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 120.3(4) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 120.4(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 119.3(3) . . ?
C17 C18 N3 116.9(3) . . ?
C13 C18 N3 123.8(3) . . ?
N4 C19 N3 119.1(2) . . ?
N4 C19 S1 125.4(2) . . ?
N3 C19 S1 115.5(2) . . ?
N5 C20 C21 126.4(3) . . ?
N5 C20 H20 116.8 . . ?
C21 C20 H20 116.8 . . ?
C22 C21 C26 118.9(3) . . ?
C22 C21 C20 117.5(3) . . ?
C26 C21 C20 123.4(3) . . ?
C23 C22 C21 121.4(3) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C22 C23 C24 121.0(3) . . ?
C22 C23 N6 118.8(4) . . ?
C24 C23 N6 120.2(4) . . ?
C25 C24 C23 118.9(3) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C24 C25 C26 122.5(3) . . ?
C24 C25 H25 118.7 . . ?
C26 C25 H25 118.7 . . ?
O1 C26 C25 119.3(3) . . ?
O1 C26 C21 123.3(3) . . ?
C25 C26 C21 117.3(3) . . ?
C10 N1 C11 118.0(3) . . ?
C10 N1 Cu1 133.6(3) . . ?
C11 N1 Cu1 108.37(19) . . ?
C1 N2 C12 118.9(2) . . ?
C1 N2 Cu1 123.2(2) . . ?
C12 N2 Cu1 117.78(19) . . ?
C19 N3 C18 129.9(3) . . ?
C19 N3 H3A 112(2) . . ?
C18 N3 H3A 116(2) . . ?
C19 N4 N5 114.0(2) . . ?
C20 N5 N4 114.1(2) . . ?
C20 N5 Cu1 124.2(2) . . ?
N4 N5 Cu1 121.60(18) . . ?
O2 N6 O3 123.8(4) . . ?
O2 N6 C23 118.3(4) . . ?
O3 N6 C23 117.9(4) . . ?
C26 O1 Cu1 126.83(19) . . ?
C19 S1 Cu1 93.92(10) . . ?
O1 Cu1 N5 92.17(9) . . ?
O1 Cu1 N2 87.85(8) . . ?
N5 Cu1 N2 177.18(10) . . ?
O1 Cu1 N1 96.24(9) . . ?
N5 Cu1 N1 105.08(10) . . ?
N2 Cu1 N1 77.72(9) . . ?
O1 Cu1 S1 161.54(7) . . ?
N5 Cu1 S1 84.93(7) . . ?
N2 Cu1 S1 94.17(7) . . ?
N1 Cu1 S1 102.12(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
N2 C1 C2 C3 1.7(5) . . . . ?
C1 C2 C3 C4 -1.5(5) . . . . ?
C2 C3 C4 C5 -178.5(3) . . . . ?
C2 C3 C4 C12 -0.3(5) . . . . ?
C3 C4 C5 C6 178.8(4) . . . . ?
C12 C4 C5 C6 0.6(5) . . . . ?
C4 C5 C6 C7 -2.3(6) . . . . ?
C5 C6 C7 C8 -175.3(4) . . . . ?
C5 C6 C7 C11 1.1(5) . . . . ?
C11 C7 C8 C9 0.9(6) . . . . ?
C6 C7 C8 C9 177.4(4) . . . . ?
C7 C8 C9 C10 -1.5(6) . . . . ?
C8 C9 C10 N1 1.8(6) . . . . ?
C8 C7 C11 N1 -0.6(5) . . . . ?
C6 C7 C11 N1 -177.3(3) . . . . ?
C8 C7 C11 C12 178.4(3) . . . . ?
C6 C7 C11 C12 1.7(4) . . . . ?
C3 C4 C12 N2 2.1(4) . . . . ?
C5 C4 C12 N2 -179.6(3) . . . . ?
C3 C4 C12 C11 -176.1(3) . . . . ?
C5 C4 C12 C11 2.2(4) . . . . ?
N1 C11 C12 N2 -2.5(4) . . . . ?
C7 C11 C12 N2 178.4(3) . . . . ?
N1 C11 C12 C4 175.7(2) . . . . ?
C7 C11 C12 C4 -3.3(4) . . . . ?
C18 C13 C14 C15 0.0(6) . . . . ?
C13 C14 C15 C16 0.1(6) . . . . ?
C14 C15 C16 C17 -0.4(6) . . . . ?
C15 C16 C17 C18 0.6(5) . . . . ?
C16 C17 C18 C13 -0.4(5) . . . . ?
C16 C17 C18 N3 -178.3(3) . . . . ?
C14 C13 C18 C17 0.1(6) . . . . ?
C14 C13 C18 N3 177.9(3) . . . . ?
N5 C20 C21 C22 -179.2(3) . . . . ?
N5 C20 C21 C26 6.2(5) . . . . ?
C26 C21 C22 C23 0.7(6) . . . . ?
C20 C21 C22 C23 -174.1(4) . . . . ?
C21 C22 C23 C24 0.3(6) . . . . ?
C21 C22 C23 N6 178.8(4) . . . . ?
C22 C23 C24 C25 -0.9(6) . . . . ?
N6 C23 C24 C25 -179.4(4) . . . . ?
C23 C24 C25 C26 0.5(6) . . . . ?
C24 C25 C26 O1 178.8(3) . . . . ?
C24 C25 C26 C21 0.5(5) . . . . ?
C22 C21 C26 O1 -179.3(3) . . . . ?
C20 C21 C26 O1 -4.8(5) . . . . ?
C22 C21 C26 C25 -1.1(5) . . . . ?
C20 C21 C26 C25 173.4(3) . . . . ?
C9 C10 N1 C11 -1.5(5) . . . . ?
C9 C10 N1 Cu1 176.1(3) . . . . ?
C7 C11 N1 C10 0.9(4) . . . . ?
C12 C11 N1 C10 -178.1(3) . . . . ?
C7 C11 N1 Cu1 -177.3(2) . . . . ?
C12 C11 N1 Cu1 3.7(3) . . . . ?
C2 C1 N2 C12 0.1(5) . . . . ?
C2 C1 N2 Cu1 176.6(3) . . . . ?
C4 C12 N2 C1 -2.0(4) . . . . ?
C11 C12 N2 C1 176.2(3) . . . . ?
C4 C12 N2 Cu1 -178.7(2) . . . . ?
C11 C12 N2 Cu1 -0.5(3) . . . . ?
N4 C19 N3 C18 -4.1(5) . . . . ?
S1 C19 N3 C18 177.2(3) . . . . ?
C17 C18 N3 C19 -162.2(3) . . . . ?
C13 C18 N3 C19 19.9(6) . . . . ?
N3 C19 N4 N5 179.5(3) . . . . ?
S1 C19 N4 N5 -1.9(4) . . . . ?
C21 C20 N5 N4 -174.1(3) . . . . ?
C21 C20 N5 Cu1 8.9(5) . . . . ?
C19 N4 N5 C20 -179.2(3) . . . . ?
C19 N4 N5 Cu1 -2.2(3) . . . . ?
C22 C23 N6 O2 1.0(8) . . . . ?
C24 C23 N6 O2 179.5(5) . . . . ?
C22 C23 N6 O3 -177.6(5) . . . . ?
C24 C23 N6 O3 0.8(8) . . . . ?
C25 C26 O1 Cu1 170.0(2) . . . . ?
C21 C26 O1 Cu1 -11.8(4) . . . . ?
N4 C19 S1 Cu1 3.9(3) . . . . ?
N3 C19 S1 Cu1 -177.4(2) . . . . ?
C26 O1 Cu1 N5 19.8(3) . . . . ?
C26 O1 Cu1 N2 -163.0(3) . . . . ?
C26 O1 Cu1 N1 -85.7(3) . . . . ?
C26 O1 Cu1 S1 100.2(3) . . . . ?
C20 N5 Cu1 O1 -17.9(3) . . . . ?
N4 N5 Cu1 O1 165.4(2) . . . . ?
C20 N5 Cu1 N1 79.2(3) . . . . ?
N4 N5 Cu1 N1 -97.5(2) . . . . ?
C20 N5 Cu1 S1 -179.6(2) . . . . ?
N4 N5 Cu1 S1 3.7(2) . . . . ?
C1 N2 Cu1 O1 -77.8(2) . . . . ?
C12 N2 Cu1 O1 98.8(2) . . . . ?
C1 N2 Cu1 N1 -174.7(3) . . . . ?
C12 N2 Cu1 N1 1.89(19) . . . . ?
C1 N2 Cu1 S1 83.8(2) . . . . ?
C12 N2 Cu1 S1 -99.62(19) . . . . ?
C10 N1 Cu1 O1 92.8(3) . . . . ?
C11 N1 Cu1 O1 -89.42(18) . . . . ?
C10 N1 Cu1 N5 -1.1(3) . . . . ?
C11 N1 Cu1 N5 176.63(18) . . . . ?
C10 N1 Cu1 N2 179.3(3) . . . . ?
C11 N1 Cu1 N2 -3.00(17) . . . . ?
C10 N1 Cu1 S1 -89.1(3) . . . . ?
C11 N1 Cu1 S1 88.68(17) . . . . ?
C19 S1 Cu1 O1 -84.9(2) . . . . ?
C19 S1 Cu1 N5 -3.31(12) . . . . ?
C19 S1 Cu1 N2 179.36(12) . . . . ?
C19 S1 Cu1 N1 101.05(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.059

#===END
