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

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

data_02
_database_code_depnum_ccdc_archive 'CCDC 1448879'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C19 H14 Cu N5), C18 H14 N4'
_chemical_formula_sum            'C56 H42 Cu2 N14'
_chemical_formula_weight         1038.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 2(1)/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                   15.071(3)
_cell_length_b                   17.319(4)
_cell_length_c                   18.468(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.99(3)
_cell_angle_gamma                90.00
_cell_volume                     4784.6(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5226
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      24.79

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2580
_exptl_absorpt_coefficient_mu    0.945
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_T_max  0.844
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27259
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         27.24
_reflns_number_total             10716
_reflns_number_gt                6567
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 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)+(0.0558P)²+0.9330P] 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         10505
_refine_ls_number_parameters     649
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1265
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
C56 C 0.0236(2) -0.0311(2) 0.2481(2) 0.0687(10) Uani 1 1 d . . .
H56 H -0.0207 0.0062 0.2486 0.082 Uiso 1 1 calc R . .
C55 C 0.0890(2) -0.1392(2) 0.24468(19) 0.0639(9) Uani 1 1 d . . .
H55 H 0.0988 -0.1921 0.2425 0.077 Uiso 1 1 calc R . .
N14 N 0.0075(2) -0.10543(18) 0.24430(19) 0.0798(9) Uani 1 1 d . . .
C54 C 0.1535(2) -0.08487(19) 0.24858(18) 0.0607(9) Uani 1 1 d . . .
H54 H 0.2146 -0.0934 0.2493 0.073 Uiso 1 1 calc R . .
C44 C 0.36509(19) 0.29894(17) 0.26865(15) 0.0450(7) Uani 1 1 d . . .
H44 H 0.4018 0.2556 0.2726 0.054 Uiso 1 1 calc R . .
Cu1 Cu 0.38435(3) -0.09668(2) 0.42057(2) 0.04845(12) Uani 1 1 d . . .
N6 N 0.36781(16) 0.11744(12) 0.51695(12) 0.0428(6) Uani 1 1 d . . .
N7 N 0.37565(17) -0.00429(13) 0.48158(13) 0.0488(6) Uani 1 1 d . . .
N9 N 0.39122(16) -0.30919(12) 0.52846(12) 0.0431(6) Uani 1 1 d . . .
C28 C 0.36914(19) 0.20048(14) 0.51698(14) 0.0403(6) Uani 1 1 d . . .
C25 C 0.36858(19) 0.36097(15) 0.51930(14) 0.0385(6) Uani 1 1 d . . .
N13 N 0.11191(16) -0.01429(14) 0.25124(12) 0.0454(6) Uani 1 1 d . . .
N8 N 0.39354(17) -0.18672(12) 0.49392(13) 0.0504(6) Uani 1 1 d . . .
C29 C 0.3325(2) 0.24117(15) 0.45558(15) 0.0451(7) Uani 1 1 d . . .
H29 H 0.3075 0.2150 0.4140 0.054 Uiso 1 1 calc R . .
C39 C 0.3507(2) 0.58305(19) 0.26256(18) 0.0576(8) Uani 1 1 d . . .
H39 H 0.2919 0.5922 0.2708 0.069 Uiso 1 1 calc R . .
C24 C 0.36981(18) 0.44757(15) 0.52049(14) 0.0389(6) Uani 1 1 d . . .
C33 C 0.3841(2) 0.06953(16) 0.46245(16) 0.0471(7) Uani 1 1 d . . .
H33 H 0.3992 0.0857 0.4175 0.057 Uiso 1 1 calc R . .
C30 C 0.3336(2) 0.32109(15) 0.45708(14) 0.0440(7) Uani 1 1 d . . .
H30 H 0.3105 0.3485 0.4157 0.053 Uiso 1 1 calc R . .
C47 C 0.27222(18) 0.28863(16) 0.26388(13) 0.0396(6) Uani 1 1 d . . .
C52 C 0.2443(2) 0.06944(18) 0.25995(15) 0.0488(7) Uani 1 1 d . . .
H52 H 0.2806 0.0260 0.2608 0.059 Uiso 1 1 calc R . .
C35 C 0.4212(2) -0.26659(16) 0.58966(16) 0.0507(8) Uani 1 1 d . . .
H35 H 0.4372 -0.2853 0.6366 0.061 Uiso 1 1 calc R . .
C42 C 0.35066(19) 0.43723(17) 0.26227(14) 0.0418(7) Uani 1 1 d . . .
C26 C 0.4040(2) 0.31905(15) 0.58028(15) 0.0444(7) Uani 1 1 d . . .
H26 H 0.4268 0.3452 0.6225 0.053 Uiso 1 1 calc R . .
C27 C 0.4059(2) 0.23912(16) 0.57932(15) 0.0466(7) Uani 1 1 d . . .
H27 H 0.4315 0.2117 0.6199 0.056 Uiso 1 1 calc R . .
C45 C 0.25846(19) 0.42864(18) 0.25905(15) 0.0482(7) Uani 1 1 d . . .
H45 H 0.2219 0.4721 0.2559 0.058 Uiso 1 1 calc R . .
C48 C 0.23086(18) 0.21022(16) 0.26239(13) 0.0387(6) Uani 1 1 d . . .
N12 N 0.39103(16) 0.51189(14) 0.25762(12) 0.0447(6) Uani 1 1 d . . .
C49 C 0.13876(19) 0.19950(18) 0.25890(15) 0.0468(7) Uani 1 1 d . . .
H49 H 0.1020 0.2426 0.2589 0.056 Uiso 1 1 calc R . .
C53 C 0.15249(18) 0.06096(17) 0.25566(14) 0.0408(7) Uani 1 1 d . . .
C36 C 0.3751(2) -0.25882(16) 0.47276(16) 0.0490(7) Uani 1 1 d . . .
H36 H 0.3537 -0.2729 0.4252 0.059 Uiso 1 1 calc R . .
C50 C 0.0998(2) 0.12651(19) 0.25537(16) 0.0507(8) Uani 1 1 d . . .
H50 H 0.0381 0.1217 0.2528 0.061 Uiso 1 1 calc R . .
C31 C 0.3477(2) 0.07206(17) 0.57397(15) 0.0516(8) Uani 1 1 d . . .
H31 H 0.3337 0.0889 0.6190 0.062 Uiso 1 1 calc R . .
C51 C 0.2824(2) 0.14268(17) 0.26298(16) 0.0493(7) Uani 1 1 d . . .
H51 H 0.3442 0.1470 0.2655 0.059 Uiso 1 1 calc R . .
C32 C 0.3526(2) -0.00208(17) 0.55121(17) 0.0533(8) Uani 1 1 d . . .
H32 H 0.3418 -0.0452 0.5788 0.064 Uiso 1 1 calc R . .
C38 C 0.3823(2) -0.12595(17) 0.32217(18) 0.0479(7) Uani 1 1 d . . .
C34 C 0.4225(2) -0.19215(16) 0.56766(17) 0.0537(8) Uani 1 1 d . . .
H34 H 0.4403 -0.1506 0.5978 0.064 Uiso 1 1 calc R . .
C46 C 0.22074(19) 0.35594(17) 0.26046(16) 0.0475(7) Uani 1 1 d . . .
H46 H 0.1590 0.3517 0.2591 0.057 Uiso 1 1 calc R . .
N11 N 0.49189(19) 0.60237(16) 0.24103(17) 0.0687(8) Uani 1 1 d . . .
C43 C 0.4041(2) 0.37126(18) 0.26776(15) 0.0475(7) Uani 1 1 d . . .
H43 H 0.4659 0.3758 0.2708 0.057 Uiso 1 1 calc R . .
C40 C 0.4130(2) 0.6364(2) 0.25304(18) 0.0613(9) Uani 1 1 d . . .
H40 H 0.4037 0.6894 0.2544 0.074 Uiso 1 1 calc R . .
C41 C 0.4759(2) 0.5278(2) 0.24417(19) 0.0615(9) Uani 1 1 d . . .
H41 H 0.5181 0.4900 0.2379 0.074 Uiso 1 1 calc R . .
N10 N 0.3814(2) -0.14565(18) 0.26353(17) 0.0719(9) Uani 1 1 d . . .
Cu2 Cu 0.14145(3) 0.63749(2) 0.41127(2) 0.05282(13) Uani 1 1 d . . .
N5 N 0.14282(17) -0.15095(13) 0.51558(13) 0.0481(6) Uani 1 1 d . . .
C11 C 0.1156(2) 0.09233(16) 0.50845(15) 0.0437(7) Uani 1 1 d . . .
N3 N 0.13014(17) 0.54435(14) 0.47458(13) 0.0521(6) Uani 1 1 d . . .
C16 C 0.0986(2) 0.05082(17) 0.56984(15) 0.0503(8) Uani 1 1 d . . .
H16 H 0.0820 0.0772 0.6099 0.060 Uiso 1 1 calc R . .
C15 C 0.1060(2) -0.02973(17) 0.57272(15) 0.0494(8) Uani 1 1 d . . .
H15 H 0.0942 -0.0568 0.6140 0.059 Uiso 1 1 calc R . .
C5 C 0.11327(19) 0.33948(16) 0.50545(15) 0.0433(7) Uani 1 1 d . . .
C2 C 0.1349(2) 0.47102(17) 0.45427(16) 0.0505(8) Uani 1 1 d . . .
H2 H 0.1506 0.4552 0.4094 0.061 Uiso 1 1 calc R . .
C8 C 0.1116(2) 0.17845(15) 0.50682(15) 0.0437(7) Uani 1 1 d . . .
C14 C 0.1314(2) -0.06853(16) 0.51224(16) 0.0451(7) Uani 1 1 d . . .
C6 C 0.0783(2) 0.29951(16) 0.44318(15) 0.0478(7) Uani 1 1 d . . .
H6 H 0.0554 0.3260 0.4012 0.057 Uiso 1 1 calc R . .
N4 N 0.11433(16) 0.42238(13) 0.50650(12) 0.0450(6) Uani 1 1 d . . .
C7 C 0.0780(2) 0.21921(16) 0.44470(15) 0.0486(7) Uani 1 1 d . . .
H7 H 0.0549 0.1922 0.4031 0.058 Uiso 1 1 calc R . .
C9 C 0.1456(2) 0.22061(17) 0.56886(16) 0.0519(8) Uani 1 1 d . . .
H9 H 0.1674 0.1945 0.6113 0.062 Uiso 1 1 calc R . .
C13 C 0.1479(2) -0.02847(17) 0.45043(15) 0.0496(7) Uani 1 1 d . . .
H13 H 0.1650 -0.0549 0.4105 0.060 Uiso 1 1 calc R . .
C4 C 0.0946(2) 0.46726(17) 0.56429(16) 0.0506(8) Uani 1 1 d . . .
H4 H 0.0779 0.4500 0.6084 0.061 Uiso 1 1 calc R . .
C12 C 0.1390(2) 0.05135(17) 0.44829(16) 0.0501(8) Uani 1 1 d . . .
H12 H 0.1488 0.0780 0.4062 0.060 Uiso 1 1 calc R . .
C1 C 0.1359(2) 0.63531(17) 0.30912(19) 0.0506(8) Uani 1 1 d . . .
C10 C 0.1472(2) 0.30045(16) 0.56777(15) 0.0498(8) Uani 1 1 d . . .
H10 H 0.1711 0.3277 0.6090 0.060 Uiso 1 1 calc R . .
C3 C 0.1044(2) 0.54134(18) 0.54363(16) 0.0536(8) Uani 1 1 d . . .
H3 H 0.0950 0.5842 0.5720 0.064 Uiso 1 1 calc R . .
N1 N 0.1288(2) 0.6302(2) 0.24775(18) 0.0799(9) Uani 1 1 d . . .
N2 N 0.15015(18) 0.72770(14) 0.47958(14) 0.0552(7) Uani 1 1 d . . .
C37 C 0.38161(19) -0.39174(14) 0.52490(15) 0.0411(7) Uani 1 1 d . . .
C23 C 0.3586(2) 0.48786(16) 0.58359(15) 0.0461(7) Uani 1 1 d . . .
H23 H 0.3474 0.4607 0.6249 0.055 Uiso 1 1 calc R . .
C21 C 0.3853(2) 0.48979(15) 0.45894(15) 0.0452(7) Uani 1 1 d . . .
H21 H 0.3917 0.4640 0.4157 0.054 Uiso 1 1 calc R . .
C22 C 0.3639(2) 0.56832(16) 0.58643(15) 0.0473(7) Uani 1 1 d . . .
H22 H 0.3557 0.5946 0.6290 0.057 Uiso 1 1 calc R . .
C20 C 0.3912(2) 0.56962(16) 0.46127(15) 0.0469(7) Uani 1 1 d . . .
H20 H 0.4017 0.5970 0.4199 0.056 Uiso 1 1 calc R . .
C18 C 0.1737(2) -0.19369(17) 0.57637(17) 0.0544(8) Uani 1 1 d . . .
H18 H 0.1887 -0.1755 0.6237 0.065 Uiso 1 1 calc R . .
C19 C 0.1778(2) -0.26750(18) 0.55310(17) 0.0566(8) Uani 1 1 d . . .
H19 H 0.1967 -0.3092 0.5828 0.068 Uiso 1 1 calc R . .
C17 C 0.1293(2) -0.20080(17) 0.45878(17) 0.0543(8) Uani 1 1 d . . .
H17 H 0.1081 -0.1866 0.4113 0.065 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
C56 N14 1.311(4) . ?
C56 N13 1.356(4) . ?
C56 H56 0.9300 . ?
C55 C54 1.348(4) . ?
C55 N14 1.360(4) . ?
C55 H55 0.9300 . ?
C54 N13 1.378(4) . ?
C54 H54 0.9300 . ?
C44 C43 1.384(4) . ?
C44 C47 1.403(4) . ?
C44 H44 0.9300 . ?
Cu1 C38 1.883(3) . ?
Cu1 N7 1.971(2) . ?
Cu1 N8 2.059(2) . ?
N6 C33 1.350(3) . ?
N6 C31 1.377(3) . ?
N6 C28 1.438(3) . ?
N7 C33 1.337(3) . ?
N7 C32 1.373(4) . ?
N9 C36 1.348(3) . ?
N9 C35 1.379(3) . ?
N9 C37 1.438(3) . ?
C28 C27 1.388(4) . ?
C28 C29 1.391(4) . ?
C25 C30 1.389(4) . ?
C25 C26 1.391(4) . ?
C25 C24 1.500(3) . ?
N13 C53 1.438(4) . ?
N8 C36 1.328(3) . ?
N8 C34 1.382(4) . ?
C29 C30 1.385(4) . ?
C29 H29 0.9300 . ?
C39 C40 1.344(4) . ?
C39 N12 1.382(4) . ?
C39 H39 0.9300 . ?
C24 C23 1.386(4) . ?
C24 C21 1.395(4) . ?
C33 H33 0.9300 . ?
C30 H30 0.9300 . ?
C47 C46 1.398(4) . ?
C47 C48 1.493(4) . ?
C52 C53 1.383(4) . ?
C52 C51 1.391(4) . ?
C52 H52 0.9300 . ?
C35 C34 1.353(4) . ?
C35 H35 0.9300 . ?
C42 C45 1.392(4) . ?
C42 C43 1.394(4) . ?
C42 N12 1.436(4) . ?
C26 C27 1.385(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C45 C46 1.383(4) . ?
C45 H45 0.9300 . ?
C48 C49 1.394(4) . ?
C48 C51 1.404(4) . ?
N12 C41 1.360(4) . ?
C49 C50 1.392(4) . ?
C49 H49 0.9300 . ?
C53 C50 1.385(4) . ?
C36 H36 0.9300 . ?
C50 H50 0.9300 . ?
C31 C32 1.356(4) . ?
C31 H31 0.9300 . ?
C51 H51 0.9300 . ?
C32 H32 0.9300 . ?
C38 N10 1.134(4) . ?
C34 H34 0.9300 . ?
C46 H46 0.9300 . ?
N11 C41 1.317(4) . ?
N11 C40 1.369(4) . ?
C43 H43 0.9300 . ?
C40 H40 0.9300 . ?
C41 H41 0.9300 . ?
Cu2 C1 1.879(3) . ?
Cu2 N2 2.002(2) . ?
Cu2 N3 2.012(2) . ?
N5 C17 1.355(4) . ?
N5 C18 1.378(4) . ?
N5 C14 1.438(3) . ?
C11 C16 1.392(4) . ?
C11 C12 1.400(4) . ?
C11 C8 1.493(4) . ?
N3 C2 1.329(3) . ?
N3 C3 1.378(4) . ?
C16 C15 1.400(4) . ?
C16 H16 0.9300 . ?
C15 C14 1.396(4) . ?
C15 H15 0.9300 . ?
C5 C10 1.378(4) . ?
C5 C6 1.390(4) . ?
C5 N4 1.436(3) . ?
C2 N4 1.345(4) . ?
C2 H2 0.9300 . ?
C8 C7 1.389(4) . ?
C8 C9 1.402(4) . ?
C14 C13 1.384(4) . ?
C6 C7 1.391(4) . ?
C6 H6 0.9300 . ?
N4 C4 1.382(3) . ?
C7 H7 0.9300 . ?
C9 C10 1.383(4) . ?
C9 H9 0.9300 . ?
C13 C12 1.389(4) . ?
C13 H13 0.9300 . ?
C4 C3 1.352(4) . ?
C4 H4 0.9300 . ?
C12 H12 0.9300 . ?
C1 N1 1.129(4) . ?
C10 H10 0.9300 . ?
C3 H3 0.9300 . ?
N2 C17 1.323(4) 1_565 ?
N2 C19 1.373(4) 1_565 ?
C37 C20 1.375(4) 1_545 ?
C37 C22 1.384(4) 1_545 ?
C23 C22 1.396(4) . ?
C23 H23 0.9300 . ?
C21 C20 1.386(4) . ?
C21 H21 0.9300 . ?
C22 C37 1.384(4) 1_565 ?
C22 H22 0.9300 . ?
C20 C37 1.375(4) 1_565 ?
C20 H20 0.9300 . ?
C18 C19 1.352(4) . ?
C18 H18 0.9300 . ?
C19 N2 1.373(4) 1_545 ?
C19 H19 0.9300 . ?
C17 N2 1.323(4) 1_545 ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N14 C56 N13 112.8(3) . . ?
N14 C56 H56 123.6 . . ?
N13 C56 H56 123.6 . . ?
C54 C55 N14 110.2(3) . . ?
C54 C55 H55 124.9 . . ?
N14 C55 H55 124.9 . . ?
C56 N14 C55 105.1(3) . . ?
C55 C54 N13 107.0(3) . . ?
C55 C54 H54 126.5 . . ?
N13 C54 H54 126.5 . . ?
C43 C44 C47 122.4(3) . . ?
C43 C44 H44 118.8 . . ?
C47 C44 H44 118.8 . . ?
C38 Cu1 N7 140.88(11) . . ?
C38 Cu1 N8 115.02(11) . . ?
N7 Cu1 N8 104.04(10) . . ?
C33 N6 C31 107.2(2) . . ?
C33 N6 C28 127.7(2) . . ?
C31 N6 C28 125.1(2) . . ?
C33 N7 C32 105.3(2) . . ?
C33 N7 Cu1 127.6(2) . . ?
C32 N7 Cu1 126.89(19) . . ?
C36 N9 C35 106.8(2) . . ?
C36 N9 C37 126.9(2) . . ?
C35 N9 C37 126.2(2) . . ?
C27 C28 C29 120.7(2) . . ?
C27 C28 N6 119.1(2) . . ?
C29 C28 N6 120.1(2) . . ?
C30 C25 C26 118.7(2) . . ?
C30 C25 C24 120.8(2) . . ?
C26 C25 C24 120.5(2) . . ?
C56 N13 C54 104.9(3) . . ?
C56 N13 C53 127.2(3) . . ?
C54 N13 C53 127.9(3) . . ?
C36 N8 C34 104.8(2) . . ?
C36 N8 Cu1 121.6(2) . . ?
C34 N8 Cu1 133.46(19) . . ?
C30 C29 C28 119.2(3) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C40 C39 N12 106.5(3) . . ?
C40 C39 H39 126.8 . . ?
N12 C39 H39 126.8 . . ?
C23 C24 C21 118.1(3) . . ?
C23 C24 C25 120.9(2) . . ?
C21 C24 C25 121.0(2) . . ?
N7 C33 N6 111.1(3) . . ?
N7 C33 H33 124.5 . . ?
N6 C33 H33 124.5 . . ?
C29 C30 C25 121.1(3) . . ?
C29 C30 H30 119.5 . . ?
C25 C30 H30 119.5 . . ?
C46 C47 C44 116.1(3) . . ?
C46 C47 C48 122.0(3) . . ?
C44 C47 C48 121.9(3) . . ?
C53 C52 C51 120.3(3) . . ?
C53 C52 H52 119.8 . . ?
C51 C52 H52 119.8 . . ?
C34 C35 N9 106.2(3) . . ?
C34 C35 H35 126.9 . . ?
N9 C35 H35 126.9 . . ?
C45 C42 C43 118.7(3) . . ?
C45 C42 N12 121.5(3) . . ?
C43 C42 N12 119.8(3) . . ?
C27 C26 C25 121.2(3) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 C28 119.1(3) . . ?
C26 C27 H27 120.5 . . ?
C28 C27 H27 120.5 . . ?
C46 C45 C42 120.5(3) . . ?
C46 C45 H45 119.8 . . ?
C42 C45 H45 119.8 . . ?
C49 C48 C51 115.9(3) . . ?
C49 C48 C47 122.2(3) . . ?
C51 C48 C47 121.9(2) . . ?
C41 N12 C39 105.2(3) . . ?
C41 N12 C42 127.4(3) . . ?
C39 N12 C42 127.3(3) . . ?
C50 C49 C48 122.3(3) . . ?
C50 C49 H49 118.8 . . ?
C48 C49 H49 118.8 . . ?
C52 C53 C50 118.8(3) . . ?
C52 C53 N13 121.0(3) . . ?
C50 C53 N13 120.2(3) . . ?
N8 C36 N9 111.9(3) . . ?
N8 C36 H36 124.1 . . ?
N9 C36 H36 124.1 . . ?
C53 C50 C49 120.4(3) . . ?
C53 C50 H50 119.8 . . ?
C49 C50 H50 119.8 . . ?
C32 C31 N6 106.2(3) . . ?
C32 C31 H31 126.9 . . ?
N6 C31 H31 126.9 . . ?
C52 C51 C48 122.2(3) . . ?
C52 C51 H51 118.9 . . ?
C48 C51 H51 118.9 . . ?
C31 C32 N7 110.2(3) . . ?
C31 C32 H32 124.9 . . ?
N7 C32 H32 124.9 . . ?
N10 C38 Cu1 178.1(3) . . ?
C35 C34 N8 110.3(3) . . ?
C35 C34 H34 124.9 . . ?
N8 C34 H34 124.9 . . ?
C45 C46 C47 122.2(3) . . ?
C45 C46 H46 118.9 . . ?
C47 C46 H46 118.9 . . ?
C41 N11 C40 104.3(3) . . ?
C44 C43 C42 120.0(3) . . ?
C44 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?
C39 C40 N11 111.1(3) . . ?
C39 C40 H40 124.4 . . ?
N11 C40 H40 124.4 . . ?
N11 C41 N12 112.8(3) . . ?
N11 C41 H41 123.6 . . ?
N12 C41 H41 123.6 . . ?
C1 Cu2 N2 129.78(12) . . ?
C1 Cu2 N3 124.82(12) . . ?
N2 Cu2 N3 105.26(10) . . ?
C17 N5 C18 107.0(2) . . ?
C17 N5 C14 126.4(3) . . ?
C18 N5 C14 126.5(2) . . ?
C16 C11 C12 118.3(3) . . ?
C16 C11 C8 121.4(3) . . ?
C12 C11 C8 120.3(3) . . ?
C2 N3 C3 104.8(2) . . ?
C2 N3 Cu2 126.2(2) . . ?
C3 N3 Cu2 128.4(2) . . ?
C11 C16 C15 121.6(3) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C14 C15 C16 118.5(3) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C10 C5 C6 120.8(3) . . ?
C10 C5 N4 118.5(3) . . ?
C6 C5 N4 120.8(2) . . ?
N3 C2 N4 111.8(3) . . ?
N3 C2 H2 124.1 . . ?
N4 C2 H2 124.1 . . ?
C7 C8 C9 118.1(3) . . ?
C7 C8 C11 122.3(3) . . ?
C9 C8 C11 119.6(3) . . ?
C13 C14 C15 120.9(3) . . ?
C13 C14 N5 120.0(3) . . ?
C15 C14 N5 119.1(3) . . ?
C5 C6 C7 118.9(3) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C2 N4 C4 107.0(2) . . ?
C2 N4 C5 128.3(2) . . ?
C4 N4 C5 124.7(2) . . ?
C8 C7 C6 121.5(3) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C14 C13 C12 119.7(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C3 C4 N4 105.9(3) . . ?
C3 C4 H4 127.0 . . ?
N4 C4 H4 127.0 . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
N1 C1 Cu2 175.6(3) . . ?
C5 C10 C9 119.8(3) . . ?
C5 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C4 C3 N3 110.5(3) . . ?
C4 C3 H3 124.8 . . ?
N3 C3 H3 124.8 . . ?
C17 N2 C19 105.3(2) 1_565 1_565 ?
C17 N2 Cu2 123.5(2) 1_565 . ?
C19 N2 Cu2 131.2(2) 1_565 . ?
C20 C37 C22 120.6(3) 1_545 1_545 ?
C20 C37 N9 120.2(2) 1_545 . ?
C22 C37 N9 119.2(2) 1_545 . ?
C24 C23 C22 121.5(3) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C20 C21 C24 120.9(3) . . ?
C20 C21 H21 119.5 . . ?
C24 C21 H21 119.5 . . ?
C37 C22 C23 118.9(3) 1_565 . ?
C37 C22 H22 120.5 1_565 . ?
C23 C22 H22 120.5 . . ?
C37 C20 C21 119.9(3) 1_565 . ?
C37 C20 H20 120.0 1_565 . ?
C21 C20 H20 120.0 . . ?
C19 C18 N5 105.8(3) . . ?
C19 C18 H18 127.1 . . ?
N5 C18 H18 127.1 . . ?
C18 C19 N2 110.6(3) . 1_545 ?
C18 C19 H19 124.7 . . ?
N2 C19 H19 124.7 1_545 . ?
N2 C17 N5 111.3(3) 1_545 . ?
N2 C17 H17 124.3 1_545 . ?
N5 C17 H17 124.3 . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.24
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.058



####################################################################### 
# 
# 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_03
_database_code_depnum_ccdc_archive 'CCDC 1869935'
_audit_update_record             
;
2018-09-26 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 Cu N3'
_chemical_formula_sum            'C7 H5 Cu N3'
_chemical_formula_weight         194.69

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   11.089(7)
_cell_length_b                   8.790(5)
_cell_length_c                   15.236(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.882(11)
_cell_angle_gamma                90
_cell_volume                     1447.6(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2281
_cell_measurement_theta_min      2.987
_cell_measurement_theta_max      28.0835

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    2.941
_shelx_estimated_absorpt_T_min   0.215
_shelx_estimated_absorpt_T_max   0.315
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.443
_exptl_absorpt_correction_T_max  0.572
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4389
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.743
_diffrn_reflns_theta_max         28.234
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1792
_reflns_number_gt                1429
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²+0.7326P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0053(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1758
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0802
_refine_ls_wR_factor_gt          0.0761
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C7 C 0.7568(3) 1.3007(2) 0.71530(14) 0.0514(6) Uani 1 1 d . . . . .
N3 N 0.7608(3) 0.9208(2) 0.76112(14) 0.0609(6) Uani 1 1 d . . . . .
Cu1 Cu 0.78524(3) 1.09951(3) 0.68784(2) 0.05032(15) Uani 1 1 d . . . . .
C3 C 0.95689(18) 0.6444(2) 0.51274(13) 0.0334(4) Uani 1 1 d . . . . .
N2 N 0.84700(18) 0.99009(19) 0.59199(12) 0.0437(4) Uani 1 1 d . . . . .
N1 N 0.90961(16) 0.79210(18) 0.52509(10) 0.0353(4) Uani 1 1 d . . . . .
C1 C 0.9922(2) 0.6096(2) 0.43404(14) 0.0438(5) Uani 1 1 d . . . . .
H1 H 0.987269 0.683083 0.389467 0.053 Uiso 1 1 calc R U . . .
C4 C 0.8670(2) 0.8995(2) 0.45958(14) 0.0403(5) Uani 1 1 d . . . . .
H4 H 0.864126 0.890448 0.398337 0.048 Uiso 1 1 calc R U . . .
C2 C 0.9649(2) 0.5343(2) 0.57874(14) 0.0447(5) Uani 1 1 d . . . . .
H2 H 0.941317 0.557437 0.632063 0.054 Uiso 1 1 calc R U . . .
C5 C 0.8302(2) 1.0203(2) 0.50147(14) 0.0415(5) Uani 1 1 d . . . . .
H5 H 0.798345 1.110224 0.473474 0.050 Uiso 1 1 calc R U . . .
C6 C 0.8950(2) 0.8525(2) 0.60304(14) 0.0440(5) Uani 1 1 d . . . . .
H6 H 0.916189 0.803047 0.658283 0.053 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C7 N3 1.146(3) 4_656 ?
C7 Cu1 1.860(2) . ?
N3 Cu1 1.980(2) . ?
Cu1 N2 1.9931(19) . ?
C3 C1 1.376(3) . ?
C3 C2 1.384(3) . ?
C3 N1 1.428(2) . ?
N2 C6 1.316(3) . ?
N2 C5 1.376(3) . ?
N1 C6 1.344(3) . ?
N1 C4 1.379(3) . ?
C1 C2 1.380(3) 5_766 ?
C4 C5 1.347(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C7 Cu1 174.64(19) 4_656 . ?
C7 N3 Cu1 164.11(18) 4_646 . ?
C7 Cu1 N3 125.16(9) . . ?
C7 Cu1 N2 136.61(8) . . ?
N3 Cu1 N2 98.22(9) . . ?
C1 C3 C2 119.52(18) . . ?
C1 C3 N1 120.07(17) . . ?
C2 C3 N1 120.40(17) . . ?
C6 N2 C5 105.41(17) . . ?
C6 N2 Cu1 122.99(14) . . ?
C5 N2 Cu1 130.52(15) . . ?
C6 N1 C4 106.23(17) . . ?
C6 N1 C3 126.60(17) . . ?
C4 N1 C3 127.15(16) . . ?
C3 C1 C2 120.04(18) . 5_766 ?
C5 C4 N1 106.71(19) . . ?
C1 C2 C3 120.45(19) 5_766 . ?
C4 C5 N2 109.60(18) . . ?
N2 C6 N1 112.04(18) . . ?

_refine_diff_density_max         0.460
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_011
_database_code_depnum_ccdc_archive 'CCDC 1474751'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Cu2 N6'
_chemical_formula_sum            'C16 H14 Cu2 N6'
_chemical_formula_weight         417.43

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'
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   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.8138(18)
_cell_length_b                   15.406(3)
_cell_length_c                   12.203(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.92(3)
_cell_angle_gamma                90.00
_cell_volume                     1650.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3723
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      27.23

_exptl_crystal_description       white
_exptl_crystal_colour            block
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1071
_exptl_absorpt_coefficient_mu    2.585
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.424
_exptl_absorpt_correction_T_max  0.460
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9446
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         27.41
_reflns_number_total             3769
_reflns_number_gt                3047
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 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)+(0.0396P)²+0.3845P] 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         3722
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C15 C 1.4119(3) 0.44032(17) 0.0503(2) 0.0503(6) Uani 1 1 d . . .
H15 H 1.3523 0.4005 0.0844 0.060 Uiso 1 1 calc R . .
C16 C 1.5726(3) 0.47597(17) -0.0914(2) 0.0510(6) Uani 1 1 d . . .
H16 H 1.6215 0.4602 -0.1529 0.061 Uiso 1 1 calc R . .
C14 C 1.4840(3) 0.41541(15) -0.0410(2) 0.0447(6) Uani 1 1 d . . .
C13 C 1.4663(3) 0.32399(16) -0.0856(2) 0.0553(7) Uani 1 1 d . . .
H13A H 1.5558 0.3088 -0.1225 0.066 Uiso 1 1 calc R . .
H13B H 1.4595 0.2839 -0.0249 0.066 Uiso 1 1 calc R . .
Cu1 Cu 0.86984(4) -0.036124(18) -0.02516(2) 0.04502(11) Uani 1 1 d . . .
Cu2 Cu 0.87518(3) 0.238361(18) -0.23369(2) 0.03993(10) Uani 1 1 d . . .
N7 N 0.8806(2) 0.14030(13) -0.13688(17) 0.0472(5) Uani 1 1 d . . .
N4 N 1.3303(2) 0.31460(11) -0.16307(16) 0.0396(4) Uani 1 1 d . . .
N3 N 1.0983(2) 0.27845(12) -0.22929(16) 0.0387(4) Uani 1 1 d . . .
N2 N 0.6404(2) -0.10575(13) 0.24954(15) 0.0395(4) Uani 1 1 d . . .
N1 N 0.7295(2) -0.06188(11) 0.09592(14) 0.0369(4) Uani 1 1 d . . .
C8 C 0.8936(3) 0.07755(15) -0.08672(19) 0.0415(5) Uani 1 1 d . . .
C6 C 0.7611(3) -0.07596(14) 0.20148(17) 0.0358(5) Uani 1 1 d . . .
H6 H 0.8562 -0.0664 0.2386 0.043 Uiso 1 1 calc R . .
C10 C 1.2005(3) 0.27403(14) -0.14336(18) 0.0373(5) Uani 1 1 d . . .
H10 H 1.1844 0.2463 -0.0776 0.045 Uiso 1 1 calc R . .
C12 C 1.3118(3) 0.34730(16) -0.2681(2) 0.0458(6) Uani 1 1 d . . .
H12 H 1.3824 0.3785 -0.3046 0.055 Uiso 1 1 calc R . .
C5 C 0.5214(3) -0.10999(16) 0.1701(2) 0.0494(6) Uani 1 1 d . . .
H5 H 0.4223 -0.1278 0.1788 0.059 Uiso 1 1 calc R . .
C7 C 0.5775(3) -0.08308(15) 0.0765(2) 0.0464(6) Uani 1 1 d . . .
H7 H 0.5217 -0.0794 0.0085 0.056 Uiso 1 1 calc R . .
C11 C 1.1691(3) 0.32455(15) -0.30716(19) 0.0447(6) Uani 1 1 d . . .
H11 H 1.1249 0.3382 -0.3770 0.054 Uiso 1 1 calc R . .
C4 C 0.6370(4) -0.12916(17) 0.36531(19) 0.0549(7) Uani 1 1 d . . .
H4A H 0.7405 -0.1388 0.3967 0.066 Uiso 1 1 calc R . .
H4B H 0.5818 -0.1833 0.3702 0.066 Uiso 1 1 calc R . .
N8 N 0.8212(2) -0.13967(14) -0.12167(16) 0.0481(5) Uani 1 1 d . . .
C9 C 0.7439(3) 0.31029(15) -0.32540(18) 0.0390(5) Uani 1 1 d . . .
C2 C 0.5634(3) -0.06071(14) 0.43280(18) 0.0403(5) Uani 1 1 d . . .
C1 C 0.5459(3) -0.07969(15) 0.54152(19) 0.0465(6) Uani 1 1 d . . .
H1 H 0.5766 -0.1335 0.5699 0.056 Uiso 1 1 calc R . .
C3 C 0.5166(3) 0.01983(16) 0.3915(2) 0.0493(6) Uani 1 1 d . . .
H3 H 0.5274 0.0334 0.3183 0.059 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
C15 C14 1.384(4) . ?
C15 C16 1.386(4) 3_865 ?
C16 C15 1.386(4) 3_865 ?
C16 C14 1.392(4) . ?
C14 C13 1.513(3) . ?
C13 N4 1.469(3) . ?
Cu1 C8 1.924(2) . ?
Cu1 N8 2.007(2) . ?
Cu1 N1 2.0458(19) . ?
Cu1 C8 2.476(3) 3_755 ?
Cu1 Cu1 2.5766(8) 3_755 ?
Cu2 C9 1.896(2) . ?
Cu2 N7 1.916(2) . ?
Cu2 N3 2.058(2) . ?
N7 C8 1.145(3) . ?
N4 C10 1.343(3) . ?
N4 C12 1.373(3) . ?
N3 C10 1.324(3) . ?
N3 C11 1.378(3) . ?
N2 C6 1.339(3) . ?
N2 C5 1.367(3) . ?
N2 C4 1.461(3) . ?
N1 C6 1.312(3) . ?
N1 C7 1.379(3) . ?
C8 Cu1 2.476(3) 3_755 ?
C12 C11 1.352(3) . ?
C5 C7 1.348(4) . ?
C4 C2 1.518(3) . ?
N8 C9 1.130(3) 2_644 ?
C9 N8 1.130(3) 2_654 ?
C2 C1 1.380(3) . ?
C2 C3 1.389(3) . ?
C1 C3 1.378(3) 3_656 ?
C3 C1 1.378(3) 3_656 ?

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
C14 C15 C16 120.8(2) . 3_865 ?
C15 C16 C14 120.4(2) 3_865 . ?
C15 C14 C16 118.9(2) . . ?
C15 C14 C13 120.5(2) . . ?
C16 C14 C13 120.6(2) . . ?
N4 C13 C14 112.1(2) . . ?
C8 Cu1 N8 121.28(9) . . ?
C8 Cu1 N1 123.45(9) . . ?
N8 Cu1 N1 99.08(8) . . ?
C8 Cu1 C8 109.59(7) . 3_755 ?
N8 Cu1 C8 104.24(9) . 3_755 ?
N1 Cu1 C8 94.86(8) . 3_755 ?
C8 Cu1 Cu1 64.87(7) . 3_755 ?
N8 Cu1 Cu1 128.61(7) . 3_755 ?
N1 Cu1 Cu1 119.54(6) . 3_755 ?
C8 Cu1 Cu1 44.71(5) 3_755 3_755 ?
C9 Cu2 N7 143.74(9) . . ?
C9 Cu2 N3 111.92(9) . . ?
N7 Cu2 N3 104.32(8) . . ?
C8 N7 Cu2 172.6(2) . . ?
C10 N4 C12 107.63(19) . . ?
C10 N4 C13 126.2(2) . . ?
C12 N4 C13 126.1(2) . . ?
C10 N3 C11 104.8(2) . . ?
C10 N3 Cu2 126.08(16) . . ?
C11 N3 Cu2 128.69(16) . . ?
C6 N2 C5 107.20(19) . . ?
C6 N2 C4 126.2(2) . . ?
C5 N2 C4 126.6(2) . . ?
C6 N1 C7 104.5(2) . . ?
C6 N1 Cu1 130.56(17) . . ?
C7 N1 Cu1 124.10(15) . . ?
N7 C8 Cu1 165.5(2) . . ?
N7 C8 Cu1 123.59(19) . 3_755 ?
Cu1 C8 Cu1 70.41(7) . 3_755 ?
N1 C6 N2 112.1(2) . . ?
N3 C10 N4 111.5(2) . . ?
C11 C12 N4 105.5(2) . . ?
C7 C5 N2 105.7(2) . . ?
C5 C7 N1 110.4(2) . . ?
C12 C11 N3 110.7(2) . . ?
N2 C4 C2 113.5(2) . . ?
C9 N8 Cu1 161.8(2) 2_644 . ?
N8 C9 Cu2 171.9(2) 2_654 . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 C4 117.6(2) . . ?
C3 C2 C4 123.5(2) . . ?
C3 C1 C2 120.8(2) 3_656 . ?
C1 C3 C2 120.2(2) 3_656 . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.41
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.062






####################################################################### 
# 
# 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_32007
_database_code_depnum_ccdc_archive 'CCDC 1448880'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H42 Cu3 N16'
_chemical_formula_sum            'C34 H42 Cu3 N16'
_chemical_formula_weight         865.49

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'
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                   8.0872(5)
_cell_length_b                   10.2331(6)
_cell_length_c                   23.4179(13)
_cell_angle_alpha                88.4500(10)
_cell_angle_beta                 80.9560(10)
_cell_angle_gamma                86.5680(10)
_cell_volume                     1910.17(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4588
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      26.35

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    1.704
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_T_max  0.736
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17744
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         28.37
_reflns_number_total             9557
_reflns_number_gt                6365
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 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)+(0.0463P)²+0.9658P] 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         9251
_refine_ls_number_parameters     481
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.82883(5) -0.22297(4) 0.339363(17) 0.03890(11) Uani 1 1 d . . .
Cu2 Cu 0.5000 0.5000 0.5000 0.03166(13) Uani 1 2 d S . .
Cu3 Cu 0.70686(5) 0.27176(4) 0.157598(18) 0.04173(12) Uani 1 1 d . . .
Cu4 Cu 0.5000 1.0000 0.0000 0.03421(14) Uani 1 2 d S . .
N11 N 0.5930(3) 0.3137(2) 0.48640(10) 0.0293(5) Uani 1 1 d . . .
N2 N 0.5828(3) 0.8152(2) 0.01824(11) 0.0331(6) Uani 1 1 d . . .
N3 N 0.2639(3) 0.9505(2) 0.03165(11) 0.0322(6) Uani 1 1 d . . .
N10 N 0.2880(3) 0.4494(2) 0.47217(11) 0.0292(5) Uani 1 1 d . . .
N12 N 0.6895(3) 0.1126(2) 0.50010(12) 0.0357(6) Uani 1 1 d . . .
N9 N 0.1111(3) 0.4192(2) 0.41235(11) 0.0298(5) Uani 1 1 d . . .
N8 N 0.5056(3) 0.0762(3) 0.29047(11) 0.0377(6) Uani 1 1 d . . .
N5 N 0.3146(3) 0.5462(3) 0.21299(12) 0.0395(6) Uani 1 1 d . . .
N1 N 0.6879(3) 0.6131(3) 0.00820(14) 0.0453(7) Uani 1 1 d . . .
N4 N 0.0363(3) 0.9186(2) 0.09426(11) 0.0347(6) Uani 1 1 d . . .
N6 N 0.5480(3) 0.4221(3) 0.19382(11) 0.0379(6) Uani 1 1 d . . .
N15 N 0.9518(5) 0.2823(3) 0.15953(14) 0.0625(9) Uani 1 1 d . . .
C29 C 0.1638(4) 0.3711(3) 0.49888(14) 0.0337(7) Uani 1 1 d . . .
H29 H 0.1563 0.3368 0.5363 0.040 Uiso 1 1 calc R . .
N7 N 0.7096(3) -0.0629(2) 0.30861(12) 0.0393(6) Uani 1 1 d . . .
C14 C 0.3906(4) 0.4402(3) 0.18579(13) 0.0365(7) Uani 1 1 d . . .
H14 H 0.3384 0.3859 0.1638 0.044 Uiso 1 1 calc R . .
C25 C 0.0987(4) 0.2868(3) 0.32609(14) 0.0392(7) Uani 1 1 d . . .
H25A H 0.0347 0.2179 0.3465 0.047 Uiso 1 1 calc R . .
H25B H 0.0700 0.2945 0.2874 0.047 Uiso 1 1 calc R . .
C24 C 0.2847(4) 0.2476(3) 0.32176(14) 0.0390(7) Uani 1 1 d . . .
H24A H 0.3492 0.3203 0.3053 0.047 Uiso 1 1 calc R . .
H24B H 0.3112 0.2295 0.3603 0.047 Uiso 1 1 calc R . .
C31 C 0.6385(3) 0.2279(3) 0.52457(13) 0.0321(7) Uani 1 1 d . . .
H31 H 0.6355 0.2450 0.5635 0.038 Uiso 1 1 calc R . .
C7 C 0.1849(4) 0.9737(3) 0.08427(14) 0.0362(7) Uani 1 1 d . . .
H7 H 0.2268 1.0223 0.1112 0.043 Uiso 1 1 calc R . .
C20 C 0.7749(4) 0.0548(3) 0.29035(14) 0.0409(8) Uani 1 1 d . . .
H20 H 0.8877 0.0723 0.2862 0.049 Uiso 1 1 calc R . .
C27 C 0.2514(3) 0.4757(3) 0.42026(13) 0.0317(7) Uani 1 1 d . . .
H27 H 0.3144 0.5269 0.3925 0.038 Uiso 1 1 calc R . .
N13 N 1.0751(4) -0.2011(3) 0.34111(12) 0.0520(8) Uani 1 1 d . . .
N14 N 0.6103(3) -0.4360(3) 0.39546(14) 0.0511(8) Uani 1 1 d . . .
C19 C 0.6851(4) -0.3602(3) 0.36938(14) 0.0363(7) Uani 1 1 d . . .
C28 C 0.0556(4) 0.3523(3) 0.46201(14) 0.0345(7) Uani 1 1 d . . .
H28 H -0.0388 0.3032 0.4691 0.041 Uiso 1 1 calc R . .
C30 C 0.6179(4) 0.2508(3) 0.43479(14) 0.0371(7) Uani 1 1 d . . .
H30 H 0.5971 0.2875 0.3997 0.045 Uiso 1 1 calc R . .
C33 C 0.7602(4) -0.0009(3) 0.52966(16) 0.0478(9) Uani 1 1 d . . .
H33A H 0.7392 -0.0802 0.5109 0.057 Uiso 1 1 calc R . .
H33B H 0.7037 -0.0050 0.5693 0.057 Uiso 1 1 calc R . .
C11 C 0.1302(4) 0.7265(3) 0.18075(15) 0.0405(8) Uani 1 1 d . . .
H11A H 0.1929 0.7194 0.1420 0.049 Uiso 1 1 calc R . .
H11B H 0.1809 0.7912 0.2010 0.049 Uiso 1 1 calc R . .
C22 C 0.5475(4) -0.0454(3) 0.30793(14) 0.0384(7) Uani 1 1 d . . .
H22 H 0.4712 -0.1096 0.3183 0.046 Uiso 1 1 calc R . .
C21 C 0.6501(4) 0.1416(3) 0.27931(14) 0.0429(8) Uani 1 1 d . . .
H21 H 0.6606 0.2281 0.2667 0.051 Uiso 1 1 calc R . .
C26 C 0.0480(4) 0.4154(3) 0.35715(14) 0.0393(7) Uani 1 1 d . . .
H26A H 0.0912 0.4873 0.3325 0.047 Uiso 1 1 calc R . .
H26B H -0.0734 0.4273 0.3641 0.047 Uiso 1 1 calc R . .
C12 C 0.1413(4) 0.5963(3) 0.21178(14) 0.0413(8) Uani 1 1 d . . .
H12A H 0.0837 0.6051 0.2512 0.050 Uiso 1 1 calc R . .
H12B H 0.0842 0.5332 0.1929 0.050 Uiso 1 1 calc R . .
C18 C 1.2023(4) -0.1973(4) 0.34439(17) 0.0500(10) Uani 1 1 d . . .
C17 C 0.5834(4) 0.1453(3) 0.12455(14) 0.0390(8) Uani 1 1 d . . .
N16 N 0.5265(4) 0.0715(3) 0.10048(14) 0.0549(8) Uani 1 1 d . . .
C32 C 0.6777(4) 0.1262(3) 0.44290(15) 0.0426(8) Uani 1 1 d . . .
H32 H 0.7054 0.0625 0.4149 0.051 Uiso 1 1 calc R . .
C8 C 0.0203(4) 0.8561(3) 0.04489(15) 0.0407(8) Uani 1 1 d . . .
H8 H -0.0698 0.8088 0.0388 0.049 Uiso 1 1 calc R . .
C6 C 0.1593(4) 0.8759(3) 0.00671(14) 0.0390(7) Uani 1 1 d . . .
H6 H 0.1814 0.8441 -0.0307 0.047 Uiso 1 1 calc R . .
C34 C 0.9472(4) 0.0049(3) 0.52941(14) 0.0432(8) Uani 1 1 d . . .
H34A H 0.9676 0.0867 0.5464 0.052 Uiso 1 1 calc R . .
H34B H 0.9833 -0.0658 0.5538 0.052 Uiso 1 1 calc R . .
C10 C -0.0507(4) 0.7722(3) 0.17710(15) 0.0415(8) Uani 1 1 d . . .
H10A H -0.0980 0.7101 0.1545 0.050 Uiso 1 1 calc R . .
H10B H -0.1148 0.7718 0.2158 0.050 Uiso 1 1 calc R . .
C23 C 0.3353(4) 0.1282(3) 0.28487(15) 0.0444(8) Uani 1 1 d . . .
H23A H 0.2566 0.0610 0.2965 0.053 Uiso 1 1 calc R . .
H23B H 0.3306 0.1514 0.2447 0.053 Uiso 1 1 calc R . .
C5 C 0.6574(4) 0.7273(3) -0.01858(14) 0.0379(7) Uani 1 1 d . . .
H5 H 0.6855 0.7425 -0.0582 0.045 Uiso 1 1 calc R . .
C4 C 0.5650(4) 0.7536(3) 0.07135(15) 0.0429(8) Uani 1 1 d . . .
H4 H 0.5158 0.7917 0.1060 0.051 Uiso 1 1 calc R . .
C9 C -0.0707(4) 0.9084(3) 0.15018(15) 0.0441(8) Uani 1 1 d . . .
H9A H -0.1868 0.9266 0.1453 0.053 Uiso 1 1 calc R . .
H9B H -0.0418 0.9731 0.1759 0.053 Uiso 1 1 calc R . .
C15 C 0.5731(5) 0.5227(3) 0.22820(16) 0.0493(9) Uani 1 1 d . . .
H15 H 0.6736 0.5365 0.2411 0.059 Uiso 1 1 calc R . .
C16 C 1.0840(4) 0.2780(4) 0.15758(19) 0.0579(11) Uani 1 1 d . . .
C3 C 0.6300(4) 0.6294(3) 0.06561(18) 0.0520(10) Uani 1 1 d . . .
H3 H 0.6345 0.5670 0.0950 0.062 Uiso 1 1 calc R . .
C1 C 0.9664(5) 0.5038(4) -0.02727(17) 0.0624(11) Uani 1 1 d . . .
H1A H 1.0188 0.4328 -0.0516 0.075 Uiso 1 1 calc R . .
H1B H 0.9969 0.5854 -0.0470 0.075 Uiso 1 1 calc R . .
C13 C 0.4295(5) 0.5995(4) 0.24073(16) 0.0526(9) Uani 1 1 d . . .
H13 H 0.4130 0.6734 0.2636 0.063 Uiso 1 1 calc R . .
C2 C 0.7752(5) 0.4961(4) -0.0204(2) 0.0640(12) Uani 1 1 d . . .
H2A H 0.7422 0.4883 -0.0582 0.077 Uiso 1 1 calc R . .
H2B H 0.7422 0.4186 0.0023 0.077 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 C19 1.924(3) . ?
Cu1 N7 2.024(3) . ?
Cu1 N13 2.024(4) . ?
Cu2 N11 2.022(2) . ?
Cu2 N11 2.022(2) 2_666 ?
Cu2 N10 2.027(2) . ?
Cu2 N10 2.027(2) 2_666 ?
Cu3 C17 1.929(4) . ?
Cu3 N15 1.998(4) . ?
Cu3 N6 2.056(3) . ?
Cu4 N3 2.025(2) 2_675 ?
Cu4 N3 2.025(2) . ?
Cu4 N2 2.026(2) . ?
Cu4 N2 2.026(2) 2_675 ?
N11 C31 1.314(4) . ?
N11 C30 1.366(4) . ?
N2 C5 1.315(4) . ?
N2 C4 1.370(4) . ?
N3 C7 1.317(4) . ?
N3 C6 1.377(4) . ?
N10 C27 1.313(4) . ?
N10 C29 1.383(4) . ?
N12 C31 1.340(4) . ?
N12 C32 1.360(4) . ?
N12 C33 1.468(4) . ?
N9 C27 1.343(4) . ?
N9 C28 1.361(4) . ?
N9 C26 1.465(4) . ?
N8 C22 1.340(4) . ?
N8 C21 1.367(4) . ?
N8 C23 1.471(4) . ?
N5 C14 1.339(4) . ?
N5 C13 1.361(4) . ?
N5 C12 1.468(4) . ?
N1 C5 1.339(4) . ?
N1 C3 1.364(5) . ?
N1 C2 1.474(4) . ?
N4 C7 1.342(4) . ?
N4 C8 1.363(4) . ?
N4 C9 1.457(4) . ?
N6 C14 1.318(4) . ?
N6 C15 1.368(4) . ?
N15 C16 1.061(4) . ?
C29 C28 1.347(4) . ?
C29 H29 0.9300 . ?
N7 C22 1.315(4) . ?
N7 C20 1.375(4) . ?
C14 H14 0.9300 . ?
C25 C24 1.521(4) . ?
C25 C26 1.524(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C24 C23 1.514(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C31 H31 0.9300 . ?
C7 H7 0.9300 . ?
C20 C21 1.355(4) . ?
C20 H20 0.9300 . ?
C27 H27 0.9300 . ?
N13 C18 1.047(4) . ?
N14 C19 1.121(4) . ?
C28 H28 0.9300 . ?
C30 C32 1.355(4) . ?
C30 H30 0.9300 . ?
C33 C34 1.516(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C11 C12 1.506(4) . ?
C11 C10 1.524(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C17 N16 1.117(4) . ?
C32 H32 0.9300 . ?
C8 C6 1.344(4) . ?
C8 H8 0.9300 . ?
C6 H6 0.9300 . ?
C34 C34 1.505(6) 2_756 ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C10 C9 1.524(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C5 H5 0.9300 . ?
C4 C3 1.348(4) . ?
C4 H4 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C15 C13 1.360(5) . ?
C15 H15 0.9300 . ?
C3 H3 0.9300 . ?
C1 C1 1.463(8) 2_765 ?
C1 C2 1.536(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C13 H13 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?

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
C19 Cu1 N7 114.82(11) . . ?
C19 Cu1 N13 131.25(12) . . ?
N7 Cu1 N13 113.53(11) . . ?
N11 Cu2 N11 180.00(14) . 2_666 ?
N11 Cu2 N10 88.26(9) . . ?
N11 Cu2 N10 91.74(9) 2_666 . ?
N11 Cu2 N10 91.74(9) . 2_666 ?
N11 Cu2 N10 88.26(9) 2_666 2_666 ?
N10 Cu2 N10 180.00(12) . 2_666 ?
C17 Cu3 N15 131.72(12) . . ?
C17 Cu3 N6 110.59(11) . . ?
N15 Cu3 N6 117.65(12) . . ?
N3 Cu4 N3 180.0 2_675 . ?
N3 Cu4 N2 91.38(9) 2_675 . ?
N3 Cu4 N2 88.62(9) . . ?
N3 Cu4 N2 88.62(9) 2_675 2_675 ?
N3 Cu4 N2 91.38(9) . 2_675 ?
N2 Cu4 N2 180.00(14) . 2_675 ?
C31 N11 C30 106.0(2) . . ?
C31 N11 Cu2 127.9(2) . . ?
C30 N11 Cu2 126.1(2) . . ?
C5 N2 C4 105.7(3) . . ?
C5 N2 Cu4 127.3(2) . . ?
C4 N2 Cu4 126.9(2) . . ?
C7 N3 C6 105.3(2) . . ?
C7 N3 Cu4 125.5(2) . . ?
C6 N3 Cu4 128.9(2) . . ?
C27 N10 C29 105.5(2) . . ?
C27 N10 Cu2 124.6(2) . . ?
C29 N10 Cu2 129.5(2) . . ?
C31 N12 C32 107.1(2) . . ?
C31 N12 C33 125.0(3) . . ?
C32 N12 C33 127.6(3) . . ?
C27 N9 C28 107.3(2) . . ?
C27 N9 C26 124.9(3) . . ?
C28 N9 C26 127.2(3) . . ?
C22 N8 C21 107.1(3) . . ?
C22 N8 C23 125.9(3) . . ?
C21 N8 C23 127.0(3) . . ?
C14 N5 C13 107.0(3) . . ?
C14 N5 C12 126.2(3) . . ?
C13 N5 C12 126.8(3) . . ?
C5 N1 C3 107.0(3) . . ?
C5 N1 C2 124.9(3) . . ?
C3 N1 C2 128.0(3) . . ?
C7 N4 C8 106.6(3) . . ?
C7 N4 C9 125.7(3) . . ?
C8 N4 C9 126.8(3) . . ?
C14 N6 C15 104.9(3) . . ?
C14 N6 Cu3 123.5(2) . . ?
C15 N6 Cu3 131.6(2) . . ?
C16 N15 Cu3 173.3(4) . . ?
C28 C29 N10 109.2(3) . . ?
C28 C29 H29 125.4 . . ?
N10 C29 H29 125.4 . . ?
C22 N7 C20 105.2(3) . . ?
C22 N7 Cu1 126.3(2) . . ?
C20 N7 Cu1 128.1(2) . . ?
N6 C14 N5 112.1(3) . . ?
N6 C14 H14 124.0 . . ?
N5 C14 H14 124.0 . . ?
C24 C25 C26 113.4(3) . . ?
C24 C25 H25A 108.9 . . ?
C26 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
C26 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C23 C24 C25 112.3(3) . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24B 109.1 . . ?
C25 C24 H24B 109.1 . . ?
H24A C24 H24B 107.9 . . ?
N11 C31 N12 111.2(3) . . ?
N11 C31 H31 124.4 . . ?
N12 C31 H31 124.4 . . ?
N3 C7 N4 111.7(3) . . ?
N3 C7 H7 124.2 . . ?
N4 C7 H7 124.2 . . ?
C21 C20 N7 109.8(3) . . ?
C21 C20 H20 125.1 . . ?
N7 C20 H20 125.1 . . ?
N10 C27 N9 111.3(3) . . ?
N10 C27 H27 124.4 . . ?
N9 C27 H27 124.4 . . ?
C18 N13 Cu1 174.9(3) . . ?
N14 C19 Cu1 168.2(3) . . ?
C29 C28 N9 106.7(3) . . ?
C29 C28 H28 126.6 . . ?
N9 C28 H28 126.6 . . ?
C32 C30 N11 109.1(3) . . ?
C32 C30 H30 125.4 . . ?
N11 C30 H30 125.4 . . ?
N12 C33 C34 112.6(3) . . ?
N12 C33 H33A 109.1 . . ?
C34 C33 H33A 109.1 . . ?
N12 C33 H33B 109.1 . . ?
C34 C33 H33B 109.1 . . ?
H33A C33 H33B 107.8 . . ?
C12 C11 C10 111.8(3) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
N7 C22 N8 111.8(3) . . ?
N7 C22 H22 124.1 . . ?
N8 C22 H22 124.1 . . ?
C20 C21 N8 106.0(3) . . ?
C20 C21 H21 127.0 . . ?
N8 C21 H21 127.0 . . ?
N9 C26 C25 112.2(2) . . ?
N9 C26 H26A 109.2 . . ?
C25 C26 H26A 109.2 . . ?
N9 C26 H26B 109.2 . . ?
C25 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?
N5 C12 C11 113.0(3) . . ?
N5 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
N5 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
N16 C17 Cu3 172.2(3) . . ?
C30 C32 N12 106.5(3) . . ?
C30 C32 H32 126.7 . . ?
N12 C32 H32 126.7 . . ?
C6 C8 N4 107.1(3) . . ?
C6 C8 H8 126.5 . . ?
N4 C8 H8 126.5 . . ?
C8 C6 N3 109.4(3) . . ?
C8 C6 H6 125.3 . . ?
N3 C6 H6 125.3 . . ?
C34 C34 C33 114.8(4) 2_756 . ?
C34 C34 H34A 108.6 2_756 . ?
C33 C34 H34A 108.6 . . ?
C34 C34 H34B 108.6 2_756 . ?
C33 C34 H34B 108.6 . . ?
H34A C34 H34B 107.5 . . ?
C9 C10 C11 114.2(3) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N8 C23 C24 111.5(3) . . ?
N8 C23 H23A 109.3 . . ?
C24 C23 H23A 109.3 . . ?
N8 C23 H23B 109.3 . . ?
C24 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
N2 C5 N1 111.4(3) . . ?
N2 C5 H5 124.3 . . ?
N1 C5 H5 124.3 . . ?
C3 C4 N2 109.4(3) . . ?
C3 C4 H4 125.3 . . ?
N2 C4 H4 125.3 . . ?
N4 C9 C10 111.1(2) . . ?
N4 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N4 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C13 C15 N6 110.0(3) . . ?
C13 C15 H15 125.0 . . ?
N6 C15 H15 125.0 . . ?
C4 C3 N1 106.6(3) . . ?
C4 C3 H3 126.7 . . ?
N1 C3 H3 126.7 . . ?
C1 C1 C2 114.3(5) 2_765 . ?
C1 C1 H1A 108.7 2_765 . ?
C2 C1 H1A 108.7 . . ?
C1 C1 H1B 108.7 2_765 . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C15 C13 N5 106.0(3) . . ?
C15 C13 H13 127.0 . . ?
N5 C13 H13 127.0 . . ?
N1 C2 C1 111.2(3) . . ?
N1 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        28.37
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.072


####################################################################### 
# 
# 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_huihui
_database_code_depnum_ccdc_archive 'CCDC 1448881'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5.62 Cu4 N6.38, C11 H18 N4'
_chemical_formula_sum            'C16.62 H18 Cu4 N10.38'
_chemical_formula_weight         617.37

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2
_symmetry_space_group_name_Hall  'P 2 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   13.0156(6)
_cell_length_b                   14.3792(7)
_cell_length_c                   12.3581(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2312.87(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4195
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      24.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    3.654
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.433
_exptl_absorpt_correction_T_max  0.448
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14112
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         28.34
_reflns_number_total             5788
_reflns_number_gt                4394
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 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)+(0.0429P)²+0.3529P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         5758
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0881
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
C8 C 1.0620(4) 0.2042(4) 0.5889(5) 0.0760(17) Uani 1 1 d . . .
H8A H 1.1063 0.2484 0.6254 0.091 Uiso 1 1 calc R . .
H8B H 1.1044 0.1679 0.5400 0.091 Uiso 1 1 calc R . .
N1 N 1.0523(7) 0.2562(10) 1.1394(6) 0.191(7) Uani 1 1 d . . .
H12 H 1.0899 0.2504 1.1961 0.230 Uiso 1 1 calc R . .
C4 C 0.8748(6) 0.1770(5) 0.9433(6) 0.104(3) Uani 1 1 d . . .
H4A H 0.8376 0.1317 0.9863 0.125 Uiso 1 1 calc R . .
H4C H 0.8252 0.2209 0.9145 0.125 Uiso 1 1 calc R . .
C13 C 0.7059(4) 0.0667(2) 0.4634(3) 0.0420(10) Uani 1 1 d . . .
Cu1 Cu 0.81173(4) -0.04534(3) 0.28023(4) 0.04180(12) Uani 1 1 d . . .
Cu2 Cu 0.67852(4) 0.06364(3) 0.21122(5) 0.04568(13) Uani 1 1 d . . .
Cu3 Cu 0.69345(5) 0.12088(3) 0.60338(4) 0.05240(15) Uani 1 1 d . . .
Cu4 Cu 0.74098(5) -0.10970(4) -0.11050(4) 0.05646(17) Uani 1 1 d . . .
N10 N 0.5402(3) 0.0165(3) 0.2144(4) 0.0528(11) Uani 0.69(4) 1 d P . .
C17 C 0.5402(3) 0.0165(3) 0.2144(4) 0.0528(11) Uani 0.31(4) 1 d P . .
N7 N 0.8009(3) -0.1785(2) 0.3272(3) 0.0510(9) Uani 1 1 d . . .
N8 N 0.9582(3) -0.0111(3) 0.2866(4) 0.0524(11) Uani 0.69(4) 1 d P . .
C18 C 0.9582(3) -0.0111(3) 0.2866(4) 0.0524(11) Uani 0.31(4) 1 d P . .
N6 N 0.7676(3) -0.0434(3) 0.1212(4) 0.0635(11) Uani 1 1 d . . .
N9 N 0.7156(3) 0.1893(3) 0.1713(3) 0.0608(11) Uani 1 1 d . . .
C16 C 0.7641(4) -0.0681(3) 0.0341(3) 0.0421(10) Uani 1 1 d . . .
N5 N 0.7313(3) 0.0354(3) 0.3852(4) 0.0665(11) Uani 1 1 d . . .
N3 N 0.9861(3) 0.2552(3) 0.5257(3) 0.0527(10) Uani 1 1 d . . .
C11 C 0.9345(4) 0.2230(4) 0.4372(4) 0.0620(13) Uani 1 1 d . . .
H11 H 0.9394 0.1635 0.4080 0.074 Uiso 1 1 calc R . .
C10 C 0.8756(4) 0.2923(4) 0.4000(5) 0.0676(14) Uani 1 1 d . . .
H10 H 0.8332 0.2904 0.3394 0.081 Uiso 1 1 calc R . .
N4 N 0.8893(4) 0.3651(3) 0.4668(4) 0.0673(12) Uani 1 1 d . . .
H13A H 0.8590 0.4180 0.4613 0.081 Uiso 1 1 calc R . .
C9 C 0.9554(4) 0.3429(3) 0.5409(4) 0.0626(14) Uani 1 1 d . . .
H9 H 0.9778 0.3819 0.5960 0.075 Uiso 1 1 calc R . .
C5 C 0.9266(7) 0.1282(4) 0.8514(6) 0.109(3) Uani 1 1 d . . .
H5A H 0.8786 0.0846 0.8193 0.131 Uiso 1 1 calc R . .
H5B H 0.9841 0.0928 0.8795 0.131 Uiso 1 1 calc R . .
C6 C 0.9647(4) 0.1929(4) 0.7654(4) 0.0643(14) Uani 1 1 d . . .
H6A H 1.0140 0.2357 0.7967 0.077 Uiso 1 1 calc R . .
H6B H 0.9076 0.2290 0.7376 0.077 Uiso 1 1 calc R . .
C14 C 0.8011(3) -0.2531(3) 0.3562(3) 0.0436(10) Uani 1 1 d . . .
C15 C 0.7332(3) 0.2635(3) 0.1455(3) 0.0421(10) Uani 1 1 d . . .
C7 C 1.0154(5) 0.1399(4) 0.6721(4) 0.0739(16) Uani 1 1 d . . .
H7A H 1.0687 0.0998 0.7010 0.089 Uiso 1 1 calc R . .
H7B H 0.9645 0.1008 0.6373 0.089 Uiso 1 1 calc R . .
N2 N 0.9487(4) 0.2274(3) 1.0139(3) 0.0637(12) Uani 1 1 d . . .
N11 N 0.6795(5) 0.0235(3) 0.7119(4) 0.0915(17) Uani 1 1 d . . .
C12 C 0.6965(5) -0.0273(3) -0.2187(4) 0.0722(16) Uani 1 1 d . . .
C2 C 0.9760(4) 0.3164(4) 1.0034(5) 0.0695(15) Uani 1 1 d . . .
H2 H 0.9527 0.3577 0.9511 0.083 Uiso 1 1 calc R . .
C3 C 0.9984(9) 0.1931(8) 1.0979(6) 0.152(5) Uani 1 1 d . . .
H3 H 0.9942 0.1321 1.1225 0.182 Uiso 1 1 calc R . .
C1 C 1.0414(7) 0.3344(8) 1.0803(8) 0.137(4) Uani 1 1 d . . .
H1 H 1.0746 0.3907 1.0923 0.164 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
C8 N3 1.457(6) . ?
C8 C7 1.510(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N1 C3 1.255(16) . ?
N1 C1 1.348(14) . ?
N1 H12 0.8600 . ?
C4 C5 1.495(8) . ?
C4 N2 1.488(8) . ?
C4 H4A 0.9700 . ?
C4 H4C 0.9700 . ?
C13 N5 1.116(5) . ?
C13 Cu3 1.904(4) . ?
Cu1 N8 1.971(4) . ?
Cu1 N7 2.006(4) . ?
Cu1 N5 2.031(5) . ?
Cu1 N6 2.047(5) . ?
Cu2 N10 1.925(4) . ?
Cu2 N9 1.934(4) . ?
Cu2 N6 2.225(4) . ?
Cu2 N5 2.294(5) . ?
Cu3 C14 1.881(4) 3_656 ?
Cu3 N11 1.947(5) . ?
Cu4 C15 1.904(4) 3_645 ?
Cu4 C16 1.909(4) . ?
Cu4 C12 1.878(5) . ?
N10 C17 1.148(7) 2_655 ?
N10 N10 1.148(7) 2_655 ?
N7 C14 1.131(5) . ?
N8 C18 1.134(7) 2_755 ?
N8 N8 1.134(7) 2_755 ?
N6 C16 1.135(5) . ?
N9 C15 1.136(5) . ?
N3 C9 1.336(6) . ?
N3 C11 1.364(6) . ?
C11 C10 1.339(7) . ?
C11 H11 0.9300 . ?
C10 N4 1.346(7) . ?
C10 H10 0.9300 . ?
N4 C9 1.295(7) . ?
N4 H13A 0.8600 . ?
C9 H9 0.9300 . ?
C5 C6 1.497(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.531(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C14 Cu3 1.881(4) 3_646 ?
C15 Cu4 1.904(4) 3_655 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N2 C3 1.318(8) . ?
N2 C2 1.334(7) . ?
N11 C12 1.148(7) 1_556 ?
C12 N11 1.148(7) 1_554 ?
C2 C1 1.302(9) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C1 H1 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C8 C7 113.7(5) . . ?
N3 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
N3 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C3 N1 C1 108.9(8) . . ?
C3 N1 H12 125.6 . . ?
C1 N1 H12 125.6 . . ?
C5 C4 N2 112.5(6) . . ?
C5 C4 H4A 109.1 . . ?
N2 C4 H4A 109.1 . . ?
C5 C4 H4C 109.1 . . ?
N2 C4 H4C 109.1 . . ?
H4A C4 H4C 107.8 . . ?
N5 C13 Cu3 167.6(4) . . ?
N8 Cu1 N7 107.13(16) . . ?
N8 Cu1 N5 109.30(16) . . ?
N7 Cu1 N5 108.95(16) . . ?
N8 Cu1 N6 107.83(17) . . ?
N7 Cu1 N6 105.72(15) . . ?
N5 Cu1 N6 117.43(17) . . ?
N10 Cu2 N9 124.60(17) . . ?
N10 Cu2 N6 104.72(17) . . ?
N9 Cu2 N6 112.85(16) . . ?
N10 Cu2 N5 101.48(17) . . ?
N9 Cu2 N5 109.27(15) . . ?
N6 Cu2 N5 100.95(16) . . ?
C14 Cu3 C13 129.19(17) 3_656 . ?
C14 Cu3 N11 120.91(18) 3_656 . ?
C13 Cu3 N11 109.84(17) . . ?
C15 Cu4 C16 119.03(17) 3_645 . ?
C15 Cu4 C12 119.79(19) 3_645 . ?
C16 Cu4 C12 121.16(18) . . ?
C17 N10 N10 0.0(6) 2_655 2_655 ?
C17 N10 Cu2 176.1(5) 2_655 . ?
N10 N10 Cu2 176.1(5) 2_655 . ?
C14 N7 Cu1 175.6(4) . . ?
C18 N8 N8 0.0(6) 2_755 2_755 ?
C18 N8 Cu1 177.0(4) 2_755 . ?
N8 N8 Cu1 177.0(4) 2_755 . ?
C16 N6 Cu1 156.6(4) . . ?
C16 N6 Cu2 132.1(4) . . ?
Cu1 N6 Cu2 71.10(14) . . ?
C15 N9 Cu2 176.9(4) . . ?
N6 C16 Cu4 173.2(4) . . ?
C13 N5 Cu1 159.5(4) . . ?
C13 N5 Cu2 130.6(4) . . ?
Cu1 N5 Cu2 69.92(16) . . ?
C9 N3 C11 106.6(4) . . ?
C9 N3 C8 127.0(5) . . ?
C11 N3 C8 126.3(5) . . ?
C10 C11 N3 107.8(5) . . ?
C10 C11 H11 126.1 . . ?
N3 C11 H11 126.1 . . ?
C11 C10 N4 106.9(5) . . ?
C11 C10 H10 126.5 . . ?
N4 C10 H10 126.5 . . ?
C9 N4 C10 109.3(5) . . ?
C9 N4 H13A 125.3 . . ?
C10 N4 H13A 125.3 . . ?
N4 C9 N3 109.4(5) . . ?
N4 C9 H9 125.3 . . ?
N3 C9 H9 125.3 . . ?
C4 C5 C6 113.4(5) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 C7 111.6(5) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N7 C14 Cu3 176.3(4) . 3_646 ?
N9 C15 Cu4 176.5(4) . 3_655 ?
C8 C7 C6 112.4(5) . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C3 N2 C2 107.7(8) . . ?
C3 N2 C4 126.7(8) . . ?
C2 N2 C4 125.6(5) . . ?
C12 N11 Cu3 162.5(6) 1_556 . ?
N11 C12 Cu4 173.1(6) 1_554 . ?
C1 C2 N2 107.1(7) . . ?
C1 C2 H2 126.5 . . ?
N2 C2 H2 126.5 . . ?
N1 C3 N2 109.0(10) . . ?
N1 C3 H3 125.5 . . ?
N2 C3 H3 125.5 . . ?
C2 C1 N1 107.3(9) . . ?
C2 C1 H1 126.3 . . ?
N1 C1 H1 126.3 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.077


