# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_SPA200
_database_code_depnum_ccdc_archive 'CCDC 1889367'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2019-06-24 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         ' 2(C34 H25 Cu3 N6 O16), 2(C6 H13 N2), H2 O'
_chemical_formula_sum            'C80 H78 Cu6 N16 O33'
_chemical_formula_weight         2172.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0018 0.0011 '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 0.0038 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0071 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3362 0.9389 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 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, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   16.471(3)
_cell_length_b                   13.801(3)
_cell_length_c                   18.659(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.86(3)
_cell_angle_gamma                90
_cell_volume                     4239.3(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    128315
_cell_measurement_theta_min      0.344
_cell_measurement_theta_max      33.749

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_F_000             2216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    0.997
_shelx_estimated_absorpt_T_min   0.817
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.600
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43339
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.625
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        21.100
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             12000
_reflns_number_gt                9536
_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       
'PAL BL2D-SMDC Program(Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.6'
_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)+(0.1166P)²+3.7669P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12000
_refine_ls_number_parameters     612
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1736
_refine_ls_wR_factor_gt          0.1653
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.084
_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
Cu1A Cu 0.32562(2) 0.15773(2) 0.51219(2) 0.01258(10) Uani 1 1 d . . . . .
O1A O 0.38596(13) 0.17882(15) 0.42152(11) 0.0133(4) Uani 1 1 d . . . . .
O2A O 0.50985(14) 0.16707(17) 0.37536(12) 0.0196(5) Uani 1 1 d . . . . .
O3A O 0.30234(14) 0.12202(18) 0.61312(12) 0.0213(5) Uani 1 1 d . . . . .
O4A O 0.36336(17) 0.0649(2) 0.71425(13) 0.0292(6) Uani 1 1 d . . . . .
N1A N 0.43278(15) 0.11985(17) 0.54421(13) 0.0120(4) Uani 1 1 d . . . . .
C1A C 0.46375(18) 0.1603(2) 0.42505(15) 0.0128(5) Uani 1 1 d . . . . .
C2A C 0.49317(17) 0.12846(19) 0.49909(15) 0.0120(5) Uani 1 1 d . . . . .
C3A C 0.57254(19) 0.1103(2) 0.52198(16) 0.0170(6) Uani 1 1 d . . . . .
H3A H 0.616313 0.116443 0.490368 0.020 Uiso 1 1 calc R U . . .
C4A C 0.5856(2) 0.0826(2) 0.59365(18) 0.0219(6) Uani 1 1 d . . . . .
H4A H 0.639206 0.068546 0.610974 0.026 Uiso 1 1 calc R U . . .
C5A C 0.5212(2) 0.0755(2) 0.63981(17) 0.0206(6) Uani 1 1 d . . . . .
H5A H 0.530100 0.057938 0.688667 0.025 Uiso 1 1 calc R U . . .
C6A C 0.4442(2) 0.0947(2) 0.61251(16) 0.0157(5) Uani 1 1 d . . . . .
C7A C 0.3647(2) 0.0927(2) 0.65140(17) 0.0202(6) Uani 1 1 d . . . . .
Cu2B Cu 0.27689(2) 0.54275(3) 0.53564(2) 0.01571(10) Uani 1 1 d . . . . .
O1B O 0.23506(13) 0.24311(15) 0.48487(13) 0.0175(4) Uani 1 1 d . . . . .
O2B O 0.30193(14) 0.37344(16) 0.52760(14) 0.0216(5) Uani 1 1 d . . . . .
O3B O 0.17356(13) 0.67161(14) 0.54798(12) 0.0140(4) Uani 1 1 d . . . . .
O4B O 0.07470(15) 0.71266(16) 0.46942(14) 0.0243(5) Uani 1 1 d . . . . .
O5B O 0.28239(14) 0.52454(17) 0.64276(13) 0.0211(5) Uani 1 1 d . . . . .
O6B O 0.37208(19) 0.5302(2) 0.73508(17) 0.0393(7) Uani 1 1 d . . . . .
O7B O 0.30422(17) 0.58933(19) 0.43704(15) 0.0291(6) Uani 1 1 d . . . . .
O8B O 0.4031(2) 0.6550(2) 0.37456(19) 0.0487(9) Uani 1 1 d . . . . .
N1B N 0.17368(15) 0.48838(17) 0.49571(13) 0.0122(4) Uani 1 1 d . . . . .
N2B N 0.38588(17) 0.58407(19) 0.55416(18) 0.0223(6) Uani 1 1 d . . . . .
C1B C 0.24214(18) 0.3330(2) 0.49857(17) 0.0153(6) Uani 1 1 d . . . . .
C2B C 0.17032(17) 0.39438(19) 0.47582(16) 0.0133(5) Uani 1 1 d . . . . .
C3B C 0.10516(19) 0.3588(2) 0.43427(18) 0.0171(6) Uani 1 1 d . . . . .
H3B H 0.102702 0.292057 0.421983 0.021 Uiso 1 1 calc R U . . .
C4B C 0.04392(19) 0.4213(2) 0.41094(18) 0.0186(6) Uani 1 1 d . . . . .
H4B H -0.000844 0.398163 0.382440 0.022 Uiso 1 1 calc R U . . .
C5B C 0.04943(18) 0.5186(2) 0.43017(17) 0.0155(5) Uani 1 1 d . . . . .
H5B H 0.009253 0.563604 0.413887 0.019 Uiso 1 1 calc R U . . .
C6B C 0.11466(18) 0.5487(2) 0.47356(16) 0.0130(5) Uani 1 1 d . . . . .
C7B C 0.12067(18) 0.6530(2) 0.49779(16) 0.0143(5) Uani 1 1 d . . . . .
C8B C 0.3540(2) 0.5377(2) 0.6716(2) 0.0255(7) Uani 1 1 d . . . . .
C9B C 0.4180(2) 0.5680(2) 0.6188(2) 0.0256(7) Uani 1 1 d . . . . .
C10B C 0.5015(2) 0.5787(3) 0.6316(3) 0.0330(9) Uani 1 1 d . . . . .
H10B H 0.526225 0.566990 0.677450 0.040 Uiso 1 1 calc R U . . .
C11B C 0.5465(2) 0.6075(3) 0.5735(3) 0.0387(11) Uani 1 1 d . . . . .
H11B H 0.603585 0.614912 0.580279 0.046 Uiso 1 1 calc R U . . .
C12B C 0.5120(2) 0.6257(3) 0.5062(3) 0.0344(10) Uani 1 1 d . . . . .
H12B H 0.543697 0.646545 0.467423 0.041 Uiso 1 1 calc R U . . .
C13B C 0.4291(2) 0.6120(2) 0.4983(2) 0.0279(8) Uani 1 1 d . . . . .
C14B C 0.3768(3) 0.6208(3) 0.4302(2) 0.0329(9) Uani 1 1 d . . . . .
Cu3C Cu 0.14918(2) 0.80644(2) 0.57516(2) 0.01022(9) Uani 1 1 d . . . . .
O1C O 0.04434(13) 0.77871(15) 0.63022(12) 0.0148(4) Uani 1 1 d . . . . .
O2C O -0.06819(14) 0.85322(18) 0.66566(14) 0.0225(5) Uani 1 1 d . . . . .
O3C O 0.22938(13) 0.87738(14) 0.51254(12) 0.0144(4) Uani 1 1 d . . . . .
O4C O 0.25828(13) 1.02589(15) 0.47173(12) 0.0151(4) Uani 1 1 d . . . . .
N1C N 0.10202(14) 0.93294(16) 0.57484(13) 0.0103(4) Uani 1 1 d . . . . .
N2C N 0.22534(15) 0.81068(18) 0.67816(13) 0.0122(4) Uani 1 1 d . . . . .
C1C C -0.00186(18) 0.8532(2) 0.63773(16) 0.0142(5) Uani 1 1 d . . . . .
C2C C 0.03174(18) 0.9453(2) 0.60709(16) 0.0138(5) Uani 1 1 d . . . . .
C3C C -0.0042(2) 1.0370(2) 0.6077(2) 0.0215(6) Uani 1 1 d . . . . .
H3C H -0.054160 1.047369 0.630582 0.026 Uiso 1 1 calc R U . . .
C4C C 0.0349(2) 1.1125(2) 0.5739(2) 0.0239(7) Uani 1 1 d . . . . .
H4C H 0.012319 1.175850 0.574667 0.029 Uiso 1 1 calc R U . . .
C5C C 0.10715(19) 1.0962(2) 0.53891(18) 0.0181(6) Uani 1 1 d . . . . .
H5C H 0.133276 1.147229 0.514446 0.022 Uiso 1 1 calc R U . . .
C6C C 0.14001(17) 1.00353(19) 0.54065(15) 0.0107(5) Uani 1 1 d . . . . .
C7C C 0.21568(17) 0.96823(19) 0.50535(15) 0.0110(5) Uani 1 1 d . . . . .
N3C N 0.30904(16) 0.8122(2) 0.79429(14) 0.0170(5) Uani 1 1 d . . . . .
H3CA H 0.342186 0.812651 0.840152 0.020 Uiso 1 1 calc R U . . .
C8C C 0.31286(18) 0.8090(2) 0.66287(16) 0.0172(6) Uani 1 1 d . . . . .
H8CA H 0.326202 0.865725 0.632939 0.021 Uiso 1 1 calc R U . . .
H8CB H 0.325372 0.749700 0.635547 0.021 Uiso 1 1 calc R U . . .
C9C C 0.36521(19) 0.8113(3) 0.73257(17) 0.0202(6) Uani 1 1 d . . . . .
H9CA H 0.400854 0.753622 0.735421 0.024 Uiso 1 1 calc R U . . .
H9CB H 0.399827 0.869994 0.733863 0.024 Uiso 1 1 calc R U . . .
C10C C 0.20502(19) 0.7256(2) 0.72284(17) 0.0175(6) Uani 1 1 d . . . . .
H10A H 0.214408 0.665437 0.695482 0.021 Uiso 1 1 calc R U . . .
H10C H 0.146797 0.728118 0.734333 0.021 Uiso 1 1 calc R U . . .
C11C C 0.2566(2) 0.7238(3) 0.79249(18) 0.0225(6) Uani 1 1 d . . . . .
H11A H 0.221152 0.723288 0.834308 0.027 Uiso 1 1 calc R U . . .
H11C H 0.290815 0.664772 0.794367 0.027 Uiso 1 1 calc R U . . .
C12C C 0.20846(18) 0.9003(2) 0.71941(16) 0.0152(5) Uani 1 1 d . . . . .
H12A H 0.149646 0.904284 0.728410 0.018 Uiso 1 1 calc R U . . .
H12C H 0.223484 0.957756 0.690925 0.018 Uiso 1 1 calc R U . . .
C13C C 0.25679(19) 0.9008(2) 0.79130(16) 0.0186(6) Uani 1 1 d . . . . .
H13A H 0.290981 0.959712 0.795111 0.022 Uiso 1 1 calc R U . . .
H13B H 0.219150 0.900670 0.831603 0.022 Uiso 1 1 calc R U . . .
N1 N 0.2517(3) 0.6684(3) 0.2877(2) 0.0448(9) Uani 1 1 d . U . . .
H1 H 0.305256 0.659569 0.313699 0.054 Uiso 1 1 calc R U . . .
N2 N 0.1154(4) 0.6923(6) 0.2200(4) 0.0856(16) Uani 1 1 d . U . . .
C1 C 0.2626(3) 0.6937(3) 0.2105(2) 0.0412(10) Uani 1 1 d . U . . .
H1A H 0.296935 0.752351 0.207078 0.049 Uiso 1 1 calc R U . . .
H1B H 0.290253 0.639854 0.186058 0.049 Uiso 1 1 calc R U . . .
C2 C 0.1829(4) 0.7115(6) 0.1754(4) 0.0740(17) Uani 1 1 d . U . . .
H2A H 0.180333 0.780045 0.159809 0.089 Uiso 1 1 calc R U . . .
H2B H 0.177772 0.670544 0.131988 0.089 Uiso 1 1 calc R U . . .
C3 C 0.2023(5) 0.7438(6) 0.3222(4) 0.089(2) Uani 1 1 d . U . . .
H3D H 0.231326 0.806609 0.322191 0.107 Uiso 1 1 calc R U . . .
H3E H 0.192536 0.725618 0.372543 0.107 Uiso 1 1 calc R U . . .
C4 C 0.1230(6) 0.7523(8) 0.2807(5) 0.115(2) Uani 1 1 d . U . . .
H4D H 0.078405 0.736794 0.313181 0.138 Uiso 1 1 calc R U . . .
H4E H 0.115858 0.820450 0.265212 0.138 Uiso 1 1 calc R U . . .
C5 C 0.2008(3) 0.5751(5) 0.2891(3) 0.0570(13) Uani 1 1 d . U . . .
H5D H 0.187951 0.559703 0.339336 0.068 Uiso 1 1 calc R U . . .
H5E H 0.233001 0.520744 0.270271 0.068 Uiso 1 1 calc R U . . .
C6 C 0.1200(5) 0.5846(7) 0.2437(5) 0.0868(19) Uani 1 1 d . U . . .
H6A H 0.120563 0.541340 0.201355 0.104 Uiso 1 1 calc R U . . .
H6B H 0.072819 0.567535 0.272725 0.104 Uiso 1 1 calc R U . . .
O1S O 0.000000 0.3430(3) 0.250000 0.0265(7) Uani 1 2 d DS T P . .
H1O1 H -0.020(3) 0.3080(18) 0.2819(14) 0.032 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1A N1A 1.918(3) . ?
Cu1A O1B 1.955(2) . ?
Cu1A O3A 1.996(2) . ?
Cu1A O1A 2.011(2) . ?
Cu1A O4C 2.249(2) 1_545 ?
O1A C1A 1.306(4) . ?
O2A C1A 1.221(4) . ?
O3A C7A 1.296(4) . ?
O4A C7A 1.234(4) . ?
N1A C6A 1.328(4) . ?
N1A C2A 1.329(4) . ?
C1A C2A 1.514(4) . ?
C2A C3A 1.385(4) . ?
C3A C4A 1.401(4) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.391(5) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.377(5) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.519(4) . ?
Cu2B N2B 1.904(3) . ?
Cu2B N1B 1.981(3) . ?
Cu2B O7B 2.014(3) . ?
Cu2B O5B 2.014(3) . ?
Cu2B O2B 2.378(2) . ?
O1B C1B 1.271(3) . ?
O2B C1B 1.241(4) . ?
O3B C7B 1.284(4) . ?
O3B Cu3C 1.973(2) . ?
O4B C7B 1.227(4) . ?
O5B C8B 1.294(4) . ?
O6B C8B 1.215(5) . ?
O7B C14B 1.282(5) . ?
O8B C14B 1.231(5) . ?
N1B C6B 1.336(4) . ?
N1B C2B 1.350(3) . ?
N2B C9B 1.321(5) . ?
N2B C13B 1.337(5) . ?
C1B C2B 1.505(4) . ?
C2B C3B 1.393(4) . ?
C3B C4B 1.386(5) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.393(4) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.388(4) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.511(4) . ?
C8B C9B 1.525(6) . ?
C9B C10B 1.395(5) . ?
C10B C11B 1.391(7) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.384(7) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.382(5) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.518(6) . ?
Cu3C N1C 1.911(2) . ?
Cu3C O3C 2.042(2) . ?
Cu3C O1C 2.073(2) . ?
Cu3C N2C 2.261(3) . ?
O1C C1C 1.289(4) . ?
O2C C1C 1.226(4) . ?
O3C C7C 1.280(3) . ?
O4C C7C 1.244(3) . ?
N1C C6C 1.332(4) . ?
N1C C2C 1.333(4) . ?
N2C C8C 1.479(4) . ?
N2C C10C 1.484(4) . ?
N2C C12C 1.488(4) . ?
C1C C2C 1.507(4) . ?
C2C C3C 1.398(4) . ?
C3C C4C 1.387(5) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.394(5) . ?
C4C H4C 0.9500 . ?
C5C C6C 1.389(4) . ?
C5C H5C 0.9500 . ?
C6C C7C 1.509(4) . ?
N3C C11C 1.494(4) . ?
N3C C13C 1.496(4) . ?
N3C C9C 1.500(4) . ?
N3C H3CA 1.0000 . ?
C8C C9C 1.537(4) . ?
C8C H8CA 0.9900 . ?
C8C H8CB 0.9900 . ?
C9C H9CA 0.9900 . ?
C9C H9CB 0.9900 . ?
C10C C11C 1.530(5) . ?
C10C H10A 0.9900 . ?
C10C H10C 0.9900 . ?
C11C H11A 0.9900 . ?
C11C H11C 0.9900 . ?
C12C C13C 1.537(4) . ?
C12C H12A 0.9900 . ?
C12C H12C 0.9900 . ?
C13C H13A 0.9900 . ?
C13C H13B 0.9900 . ?
N1 C3 1.481(7) . ?
N1 C1 1.500(5) . ?
N1 C5 1.538(7) . ?
N1 H1 1.0000 . ?
N2 C4 1.406(11) . ?
N2 C2 1.435(8) . ?
N2 C6 1.551(10) . ?
C1 C2 1.468(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.502(11) . ?
C3 H3D 0.9900 . ?
C3 H3E 0.9900 . ?
C4 H4D 0.9900 . ?
C4 H4E 0.9900 . ?
C5 C6 1.560(9) . ?
C5 H5D 0.9900 . ?
C5 H5E 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
O1S H1O1 0.840(13) . ?
O1S H1O1 0.840(13) 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
N1A Cu1A O1B 158.76(10) . . ?
N1A Cu1A O3A 80.89(10) . . ?
O1B Cu1A O3A 103.09(10) . . ?
N1A Cu1A O1A 80.01(10) . . ?
O1B Cu1A O1A 95.00(9) . . ?
O3A Cu1A O1A 160.89(10) . . ?
N1A Cu1A O4C 108.85(9) . 1_545 ?
O1B Cu1A O4C 92.08(9) . 1_545 ?
O3A Cu1A O4C 90.53(9) . 1_545 ?
O1A Cu1A O4C 94.97(8) . 1_545 ?
C1A O1A Cu1A 116.11(18) . . ?
C7A O3A Cu1A 115.11(19) . . ?
C6A N1A C2A 123.0(3) . . ?
C6A N1A Cu1A 118.1(2) . . ?
C2A N1A Cu1A 118.6(2) . . ?
O2A C1A O1A 125.4(3) . . ?
O2A C1A C2A 121.8(3) . . ?
O1A C1A C2A 112.8(2) . . ?
N1A C2A C3A 120.5(3) . . ?
N1A C2A C1A 112.3(3) . . ?
C3A C2A C1A 127.2(3) . . ?
C2A C3A C4A 117.3(3) . . ?
C2A C3A H3A 121.4 . . ?
C4A C3A H3A 121.4 . . ?
C5A C4A C3A 120.9(3) . . ?
C5A C4A H4A 119.6 . . ?
C3A C4A H4A 119.6 . . ?
C6A C5A C4A 118.0(3) . . ?
C6A C5A H5A 121.0 . . ?
C4A C5A H5A 121.0 . . ?
N1A C6A C5A 120.4(3) . . ?
N1A C6A C7A 111.4(3) . . ?
C5A C6A C7A 128.2(3) . . ?
O4A C7A O3A 125.6(3) . . ?
O4A C7A C6A 120.1(3) . . ?
O3A C7A C6A 114.3(3) . . ?
N2B Cu2B N1B 166.86(12) . . ?
N2B Cu2B O7B 80.38(13) . . ?
N1B Cu2B O7B 89.53(11) . . ?
N2B Cu2B O5B 81.11(12) . . ?
N1B Cu2B O5B 109.66(10) . . ?
O7B Cu2B O5B 160.50(10) . . ?
N2B Cu2B O2B 98.12(10) . . ?
N1B Cu2B O2B 75.68(9) . . ?
O7B Cu2B O2B 102.22(10) . . ?
O5B Cu2B O2B 86.43(9) . . ?
C1B O1B Cu1A 118.1(2) . . ?
C1B O2B Cu2B 109.43(19) . . ?
C7B O3B Cu3C 103.71(17) . . ?
C8B O5B Cu2B 114.0(2) . . ?
C14B O7B Cu2B 115.9(3) . . ?
C6B N1B C2B 119.4(3) . . ?
C6B N1B Cu2B 119.15(19) . . ?
C2B N1B Cu2B 119.6(2) . . ?
C9B N2B C13B 123.5(3) . . ?
C9B N2B Cu2B 117.6(3) . . ?
C13B N2B Cu2B 117.9(3) . . ?
O2B C1B O1B 126.4(3) . . ?
O2B C1B C2B 118.4(2) . . ?
O1B C1B C2B 115.3(3) . . ?
N1B C2B C3B 121.0(3) . . ?
N1B C2B C1B 116.0(3) . . ?
C3B C2B C1B 122.9(2) . . ?
C4B C3B C2B 119.7(3) . . ?
C4B C3B H3B 120.1 . . ?
C2B C3B H3B 120.1 . . ?
C3B C4B C5B 118.6(3) . . ?
C3B C4B H4B 120.7 . . ?
C5B C4B H4B 120.7 . . ?
C6B C5B C4B 118.8(3) . . ?
C6B C5B H5B 120.6 . . ?
C4B C5B H5B 120.6 . . ?
N1B C6B C5B 122.4(3) . . ?
N1B C6B C7B 117.5(3) . . ?
C5B C6B C7B 120.1(3) . . ?
O4B C7B O3B 125.1(3) . . ?
O4B C7B C6B 118.5(3) . . ?
O3B C7B C6B 116.4(3) . . ?
O6B C8B O5B 125.8(4) . . ?
O6B C8B C9B 120.0(3) . . ?
O5B C8B C9B 114.2(3) . . ?
N2B C9B C10B 120.1(4) . . ?
N2B C9B C8B 111.8(3) . . ?
C10B C9B C8B 128.1(4) . . ?
C11B C10B C9B 116.4(4) . . ?
C11B C10B H10B 121.8 . . ?
C9B C10B H10B 121.8 . . ?
C12B C11B C10B 123.0(4) . . ?
C12B C11B H11B 118.5 . . ?
C10B C11B H11B 118.5 . . ?
C13B C12B C11B 116.5(4) . . ?
C13B C12B H12B 121.7 . . ?
C11B C12B H12B 121.7 . . ?
N2B C13B C12B 120.4(4) . . ?
N2B C13B C14B 112.0(3) . . ?
C12B C13B C14B 127.6(4) . . ?
O8B C14B O7B 124.6(5) . . ?
O8B C14B C13B 122.1(4) . . ?
O7B C14B C13B 113.2(3) . . ?
N1C Cu3C O3B 161.23(10) . . ?
N1C Cu3C O3C 80.25(9) . . ?
O3B Cu3C O3C 99.45(9) . . ?
N1C Cu3C O1C 79.93(9) . . ?
O3B Cu3C O1C 97.64(9) . . ?
O3C Cu3C O1C 159.51(8) . . ?
N1C Cu3C N2C 101.14(10) . . ?
O3B Cu3C N2C 97.52(9) . . ?
O3C Cu3C N2C 97.04(9) . . ?
O1C Cu3C N2C 91.82(9) . . ?
C1C O1C Cu3C 114.25(18) . . ?
C7C O3C Cu3C 114.49(18) . . ?
C7C O4C Cu1A 128.93(19) . 1_565 ?
C6C N1C C2C 123.4(2) . . ?
C6C N1C Cu3C 118.20(19) . . ?
C2C N1C Cu3C 118.33(19) . . ?
C8C N2C C10C 109.6(2) . . ?
C8C N2C C12C 108.2(2) . . ?
C10C N2C C12C 108.5(2) . . ?
C8C N2C Cu3C 110.68(18) . . ?
C10C N2C Cu3C 109.14(18) . . ?
C12C N2C Cu3C 110.68(18) . . ?
O2C C1C O1C 125.7(3) . . ?
O2C C1C C2C 120.3(3) . . ?
O1C C1C C2C 114.0(2) . . ?
N1C C2C C3C 119.6(3) . . ?
N1C C2C C1C 113.5(2) . . ?
C3C C2C C1C 126.9(3) . . ?
C4C C3C C2C 118.3(3) . . ?
C4C C3C H3C 120.9 . . ?
C2C C3C H3C 120.9 . . ?
C3C C4C C5C 120.5(3) . . ?
C3C C4C H4C 119.8 . . ?
C5C C4C H4C 119.8 . . ?
C6C C5C C4C 118.4(3) . . ?
C6C C5C H5C 120.8 . . ?
C4C C5C H5C 120.8 . . ?
N1C C6C C5C 119.7(3) . . ?
N1C C6C C7C 112.4(2) . . ?
C5C C6C C7C 127.9(3) . . ?
O4C C7C O3C 125.4(3) . . ?
O4C C7C C6C 120.1(2) . . ?
O3C C7C C6C 114.6(2) . . ?
C11C N3C C13C 109.6(3) . . ?
C11C N3C C9C 110.3(3) . . ?
C13C N3C C9C 110.2(2) . . ?
C11C N3C H3CA 108.9 . . ?
C13C N3C H3CA 108.9 . . ?
C9C N3C H3CA 108.9 . . ?
N2C C8C C9C 111.1(2) . . ?
N2C C8C H8CA 109.4 . . ?
C9C C8C H8CA 109.4 . . ?
N2C C8C H8CB 109.4 . . ?
C9C C8C H8CB 109.4 . . ?
H8CA C8C H8CB 108.0 . . ?
N3C C9C C8C 107.9(2) . . ?
N3C C9C H9CA 110.1 . . ?
C8C C9C H9CA 110.1 . . ?
N3C C9C H9CB 110.1 . . ?
C8C C9C H9CB 110.1 . . ?
H9CA C9C H9CB 108.4 . . ?
N2C C10C C11C 111.2(3) . . ?
N2C C10C H10A 109.4 . . ?
C11C C10C H10A 109.4 . . ?
N2C C10C H10C 109.4 . . ?
C11C C10C H10C 109.4 . . ?
H10A C10C H10C 108.0 . . ?
N3C C11C C10C 108.1(3) . . ?
N3C C11C H11A 110.1 . . ?
C10C C11C H11A 110.1 . . ?
N3C C11C H11C 110.1 . . ?
C10C C11C H11C 110.1 . . ?
H11A C11C H11C 108.4 . . ?
N2C C12C C13C 110.8(2) . . ?
N2C C12C H12A 109.5 . . ?
C13C C12C H12A 109.5 . . ?
N2C C12C H12C 109.5 . . ?
C13C C12C H12C 109.5 . . ?
H12A C12C H12C 108.1 . . ?
N3C C13C C12C 108.1(2) . . ?
N3C C13C H13A 110.1 . . ?
C12C C13C H13A 110.1 . . ?
N3C C13C H13B 110.1 . . ?
C12C C13C H13B 110.1 . . ?
H13A C13C H13B 108.4 . . ?
C3 N1 C1 109.8(4) . . ?
C3 N1 C5 105.8(5) . . ?
C1 N1 C5 107.1(4) . . ?
C3 N1 H1 111.3 . . ?
C1 N1 H1 111.3 . . ?
C5 N1 H1 111.3 . . ?
C4 N2 C2 107.9(8) . . ?
C4 N2 C6 109.4(7) . . ?
C2 N2 C6 108.1(6) . . ?
C2 C1 N1 109.5(4) . . ?
C2 C1 H1A 109.8 . . ?
N1 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
N1 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
N2 C2 C1 114.2(5) . . ?
N2 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
N2 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
N1 C3 C4 108.2(6) . . ?
N1 C3 H3D 110.1 . . ?
C4 C3 H3D 110.1 . . ?
N1 C3 H3E 110.1 . . ?
C4 C3 H3E 110.1 . . ?
H3D C3 H3E 108.4 . . ?
N2 C4 C3 115.0(6) . . ?
N2 C4 H4D 108.5 . . ?
C3 C4 H4D 108.5 . . ?
N2 C4 H4E 108.5 . . ?
C3 C4 H4E 108.5 . . ?
H4D C4 H4E 107.5 . . ?
N1 C5 C6 112.1(5) . . ?
N1 C5 H5D 109.2 . . ?
C6 C5 H5D 109.2 . . ?
N1 C5 H5E 109.2 . . ?
C6 C5 H5E 109.2 . . ?
H5D C5 H5E 107.9 . . ?
N2 C6 C5 105.6(6) . . ?
N2 C6 H6A 110.6 . . ?
C5 C6 H6A 110.6 . . ?
N2 C6 H6B 110.6 . . ?
C5 C6 H6B 110.6 . . ?
H6A C6 H6B 108.8 . . ?
H1O1 O1S H1O1 110(3) . 2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1A O1A C1A O2A 178.6(2) . . . . ?
Cu1A O1A C1A C2A -1.5(3) . . . . ?
C6A N1A C2A C3A 0.5(4) . . . . ?
Cu1A N1A C2A C3A 174.1(2) . . . . ?
C6A N1A C2A C1A -178.6(2) . . . . ?
Cu1A N1A C2A C1A -5.0(3) . . . . ?
O2A C1A C2A N1A -176.0(3) . . . . ?
O1A C1A C2A N1A 4.1(3) . . . . ?
O2A C1A C2A C3A 5.0(5) . . . . ?
O1A C1A C2A C3A -175.0(3) . . . . ?
N1A C2A C3A C4A 0.2(4) . . . . ?
C1A C2A C3A C4A 179.2(3) . . . . ?
C2A C3A C4A C5A -1.1(5) . . . . ?
C3A C4A C5A C6A 1.2(5) . . . . ?
C2A N1A C6A C5A -0.4(4) . . . . ?
Cu1A N1A C6A C5A -174.0(2) . . . . ?
C2A N1A C6A C7A 178.9(2) . . . . ?
Cu1A N1A C6A C7A 5.2(3) . . . . ?
C4A C5A C6A N1A -0.5(5) . . . . ?
C4A C5A C6A C7A -179.6(3) . . . . ?
Cu1A O3A C7A O4A -178.1(3) . . . . ?
Cu1A O3A C7A C6A 2.2(3) . . . . ?
N1A C6A C7A O4A 175.5(3) . . . . ?
C5A C6A C7A O4A -5.3(5) . . . . ?
N1A C6A C7A O3A -4.7(4) . . . . ?
C5A C6A C7A O3A 174.5(3) . . . . ?
Cu2B O2B C1B O1B 179.0(3) . . . . ?
Cu2B O2B C1B C2B -0.1(3) . . . . ?
Cu1A O1B C1B O2B 0.6(4) . . . . ?
Cu1A O1B C1B C2B 179.76(19) . . . . ?
C6B N1B C2B C3B -1.8(4) . . . . ?
Cu2B N1B C2B C3B -166.5(2) . . . . ?
C6B N1B C2B C1B 175.7(3) . . . . ?
Cu2B N1B C2B C1B 11.1(3) . . . . ?
O2B C1B C2B N1B -6.5(4) . . . . ?
O1B C1B C2B N1B 174.2(3) . . . . ?
O2B C1B C2B C3B 170.9(3) . . . . ?
O1B C1B C2B C3B -8.3(4) . . . . ?
N1B C2B C3B C4B 2.1(4) . . . . ?
C1B C2B C3B C4B -175.3(3) . . . . ?
C2B C3B C4B C5B -0.2(5) . . . . ?
C3B C4B C5B C6B -1.8(5) . . . . ?
C2B N1B C6B C5B -0.3(4) . . . . ?
Cu2B N1B C6B C5B 164.4(2) . . . . ?
C2B N1B C6B C7B 179.4(3) . . . . ?
Cu2B N1B C6B C7B -15.9(3) . . . . ?
C4B C5B C6B N1B 2.1(5) . . . . ?
C4B C5B C6B C7B -177.6(3) . . . . ?
Cu3C O3B C7B O4B 8.5(4) . . . . ?
Cu3C O3B C7B C6B -170.4(2) . . . . ?
N1B C6B C7B O4B 168.7(3) . . . . ?
C5B C6B C7B O4B -11.5(4) . . . . ?
N1B C6B C7B O3B -12.3(4) . . . . ?
C5B C6B C7B O3B 167.4(3) . . . . ?
Cu2B O5B C8B O6B -179.6(3) . . . . ?
Cu2B O5B C8B C9B 2.3(4) . . . . ?
C13B N2B C9B C10B -0.9(5) . . . . ?
Cu2B N2B C9B C10B 167.3(3) . . . . ?
C13B N2B C9B C8B 179.6(3) . . . . ?
Cu2B N2B C9B C8B -12.2(4) . . . . ?
O6B C8B C9B N2B -172.2(3) . . . . ?
O5B C8B C9B N2B 6.1(4) . . . . ?
O6B C8B C9B C10B 8.4(6) . . . . ?
O5B C8B C9B C10B -173.3(3) . . . . ?
N2B C9B C10B C11B 0.6(5) . . . . ?
C8B C9B C10B C11B -180.0(3) . . . . ?
C9B C10B C11B C12B 0.5(5) . . . . ?
C10B C11B C12B C13B -1.3(5) . . . . ?
C9B N2B C13B C12B 0.0(5) . . . . ?
Cu2B N2B C13B C12B -168.2(2) . . . . ?
C9B N2B C13B C14B 177.6(3) . . . . ?
Cu2B N2B C13B C14B 9.5(4) . . . . ?
C11B C12B C13B N2B 1.1(5) . . . . ?
C11B C12B C13B C14B -176.2(3) . . . . ?
Cu2B O7B C14B O8B -177.5(3) . . . . ?
Cu2B O7B C14B C13B 2.7(4) . . . . ?
N2B C13B C14B O8B 172.4(4) . . . . ?
C12B C13B C14B O8B -10.1(6) . . . . ?
N2B C13B C14B O7B -7.7(4) . . . . ?
C12B C13B C14B O7B 169.8(3) . . . . ?
Cu3C O1C C1C O2C 176.8(3) . . . . ?
Cu3C O1C C1C C2C -2.0(3) . . . . ?
C6C N1C C2C C3C -1.9(4) . . . . ?
Cu3C N1C C2C C3C -180.0(2) . . . . ?
C6C N1C C2C C1C 176.1(3) . . . . ?
Cu3C N1C C2C C1C -1.9(3) . . . . ?
O2C C1C C2C N1C -176.3(3) . . . . ?
O1C C1C C2C N1C 2.6(4) . . . . ?
O2C C1C C2C C3C 1.5(5) . . . . ?
O1C C1C C2C C3C -179.6(3) . . . . ?
N1C C2C C3C C4C 0.3(5) . . . . ?
C1C C2C C3C C4C -177.4(3) . . . . ?
C2C C3C C4C C5C 1.6(6) . . . . ?
C3C C4C C5C C6C -2.0(5) . . . . ?
C2C N1C C6C C5C 1.5(4) . . . . ?
Cu3C N1C C6C C5C 179.6(2) . . . . ?
C2C N1C C6C C7C -176.6(3) . . . . ?
Cu3C N1C C6C C7C 1.5(3) . . . . ?
C4C C5C C6C N1C 0.5(5) . . . . ?
C4C C5C C6C C7C 178.2(3) . . . . ?
Cu1A O4C C7C O3C -119.3(3) 1_565 . . . ?
Cu1A O4C C7C C6C 61.9(4) 1_565 . . . ?
Cu3C O3C C7C O4C 177.4(2) . . . . ?
Cu3C O3C C7C C6C -3.7(3) . . . . ?
N1C C6C C7C O4C -179.4(3) . . . . ?
C5C C6C C7C O4C 2.7(5) . . . . ?
N1C C6C C7C O3C 1.6(4) . . . . ?
C5C C6C C7C O3C -176.3(3) . . . . ?
C10C N2C C8C C9C -59.3(3) . . . . ?
C12C N2C C8C C9C 58.9(3) . . . . ?
Cu3C N2C C8C C9C -179.7(2) . . . . ?
C11C N3C C9C C8C 59.7(3) . . . . ?
C13C N3C C9C C8C -61.4(3) . . . . ?
N2C C8C C9C N3C 1.3(4) . . . . ?
C8C N2C C10C C11C 57.2(3) . . . . ?
C12C N2C C10C C11C -60.7(3) . . . . ?
Cu3C N2C C10C C11C 178.5(2) . . . . ?
C13C N3C C11C C10C 59.6(3) . . . . ?
C9C N3C C11C C10C -61.9(3) . . . . ?
N2C C10C C11C N3C 2.5(4) . . . . ?
C8C N2C C12C C13C -61.6(3) . . . . ?
C10C N2C C12C C13C 57.3(3) . . . . ?
Cu3C N2C C12C C13C 177.00(19) . . . . ?
C11C N3C C13C C12C -62.8(3) . . . . ?
C9C N3C C13C C12C 58.8(3) . . . . ?
N2C C12C C13C N3C 3.1(3) . . . . ?
C3 N1 C1 C2 -53.1(7) . . . . ?
C5 N1 C1 C2 61.4(6) . . . . ?
C4 N2 C2 C1 59.5(9) . . . . ?
C6 N2 C2 C1 -58.8(9) . . . . ?
N1 C1 C2 N2 -5.4(9) . . . . ?
C1 N1 C3 C4 56.8(8) . . . . ?
C5 N1 C3 C4 -58.5(8) . . . . ?
C2 N2 C4 C3 -55.0(11) . . . . ?
C6 N2 C4 C3 62.4(11) . . . . ?
N1 C3 C4 N2 -2.2(12) . . . . ?
C3 N1 C5 C6 63.6(7) . . . . ?
C1 N1 C5 C6 -53.5(6) . . . . ?
C4 N2 C6 C5 -54.3(8) . . . . ?
C2 N2 C6 C5 62.9(8) . . . . ?
N1 C5 C6 N2 -6.7(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O7B 1.00 2.50 3.090(5) 117.5 . yes
N1 H1 O8B 1.00 1.94 2.935(6) 171.7 . yes
O1S H1O1 O1C 0.840(13) 2.081(17) 2.908(3) 168(5) 3_566 yes
N3C H3CA O1A 1.00 1.66 2.657(3) 171.8 4_566 yes

_refine_diff_density_max         3.099
_refine_diff_density_min         -1.340
_refine_diff_density_rms         0.164


# start Validation Reply Form
_vrf_PLAT097_SPA200              
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       3.10 eA-3  
RESPONSE: The five of significant highest difference peaks are scattered 
across the asymmetric unit,with the largest peak being located ca. 0.74 \%A 
from H6A of free dabco molecule,the other residual peaks exist near the 
free dabco molecule. Generally, the residual peaks are due to poor data 
quality resulting from a damaged crystal, unresolved twinning or from 
the poor crstallinity or disordered solvent. Even though attempts to 
several model  these peaks were made, but without success. Also, twinninig 
possiblilites were explored thoroughly and did not produce a significant 
reduction in the peak height. Several absorption correction and diorded 
model were not helpful to improve the structure for R1 value. 
 
;
# end Validation Reply Form
####################################################################### 
# 
# 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_SPA268
_database_code_depnum_ccdc_archive 'CCDC 1889372'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2019-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Cu2 N4 O10, H2 O'
_chemical_formula_sum            'C24 H20 Cu2 N4 O11'
_chemical_formula_weight         667.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3383 1.0252 '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                   14.695(3)
_cell_length_b                   5.1650(10)
_cell_length_c                   31.873(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.29(3)
_cell_angle_gamma                90
_cell_volume                     2412.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    35059
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_F_000             1352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.061
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.007
_exptl_absorpt_coefficient_mu    1.324
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10774
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.272
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             3080
_reflns_number_gt                2664
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4(Putz&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.0459P)²+3.1844P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3080
_refine_ls_number_parameters     195
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.46373(2) 0.54628(5) 0.38877(2) 0.01669(10) Uani 1 1 d . . . . .
O1 O 0.42669(11) 0.8512(3) 0.42218(5) 0.0216(3) Uani 1 1 d . . . . .
O2 O 0.32757(12) 1.1822(3) 0.41826(5) 0.0278(4) Uani 1 1 d . . . . .
O3 O 0.46371(10) 0.2665(3) 0.34327(4) 0.0182(3) Uani 1 1 d . . . . .
O4 O 0.38531(11) 0.1451(3) 0.28339(5) 0.0232(3) Uani 1 1 d . . . . .
N1 N 0.35644(12) 0.6428(3) 0.35520(5) 0.0143(3) Uani 1 1 d . . . . .
N2 N 0.56324(13) 0.4297(3) 0.42886(5) 0.0165(4) Uani 1 1 d . . . . .
C1 C 0.35674(15) 0.9754(4) 0.40606(6) 0.0177(4) Uani 1 1 d . . . . .
C2 C 0.31006(14) 0.8461(4) 0.36739(6) 0.0155(4) Uani 1 1 d . . . . .
C3 C 0.23017(15) 0.9208(4) 0.34464(7) 0.0196(4) Uani 1 1 d . . . . .
H3 H 0.196335 1.063920 0.352964 0.024 Uiso 1 1 calc R U . . .
C4 C 0.20175(15) 0.7774(5) 0.30913(7) 0.0221(5) Uani 1 1 d . . . . .
H4 H 0.147561 0.823118 0.293334 0.027 Uiso 1 1 calc R U . . .
C5 C 0.25222(16) 0.5678(4) 0.29670(7) 0.0202(4) Uani 1 1 d . . . . .
H5 H 0.233386 0.471812 0.272543 0.024 Uiso 1 1 calc R U . . .
C6 C 0.33145(15) 0.5040(4) 0.32102(6) 0.0164(4) Uani 1 1 d . . . . .
C7 C 0.39782(15) 0.2861(4) 0.31426(6) 0.0163(4) Uani 1 1 d . . . . .
C8 C 0.58301(16) 0.5632(4) 0.46464(7) 0.0197(4) Uani 1 1 d . . . . .
H8 H 0.546689 0.706741 0.470430 0.024 Uiso 1 1 calc R U . . .
C9 C 0.65478(16) 0.4972(4) 0.49327(6) 0.0203(4) Uani 1 1 d . . . . .
H9 H 0.666238 0.594602 0.518008 0.024 Uiso 1 1 calc R U . . .
C10 C 0.71004(13) 0.2859(4) 0.48534(6) 0.0142(4) Uani 1 1 d . . . . .
C11 C 0.68774(15) 0.1470(4) 0.44864(6) 0.0182(4) Uani 1 1 d . . . . .
H11 H 0.722338 0.001104 0.442218 0.022 Uiso 1 1 calc R U . . .
C12 C 0.61477(15) 0.2231(4) 0.42160(6) 0.0192(4) Uani 1 1 d . . . . .
H12 H 0.600726 0.125712 0.397058 0.023 Uiso 1 1 calc R U . . .
O5 O 0.55200(11) 0.7948(3) 0.34216(5) 0.0227(3) Uani 1 1 d D . . . .
H1O5 H 0.528(2) 0.940(3) 0.3435(9) 0.034 Uiso 1 1 d D U . . .
H2O5 H 0.5435(19) 0.740(5) 0.3178(5) 0.034 Uiso 1 1 d D U . . .
O6 O 0.500000 -0.2256(5) 0.250000 0.0335(6) Uani 1 2 d DS T P . .
H1O6 H 0.4634(19) -0.115(5) 0.2583(12) 0.050 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.9044(18) . ?
Cu1 N2 1.9632(18) . ?
Cu1 O1 1.9991(16) . ?
Cu1 O3 2.0473(15) . ?
Cu1 O5 2.4137(18) . ?
O1 C1 1.286(3) . ?
O2 C1 1.225(3) . ?
O3 C7 1.292(2) . ?
O4 C7 1.227(3) . ?
N1 C2 1.326(3) . ?
N1 C6 1.333(3) . ?
N2 C12 1.339(3) . ?
N2 C8 1.346(3) . ?
C1 C2 1.519(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.390(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.515(3) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.395(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.390(3) . ?
C10 C10 1.492(4) 7_656 ?
C11 C12 1.382(3) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
O5 H1O5 0.829(10) . ?
O5 H2O5 0.825(10) . ?
O6 H1O6 0.839(10) . ?
O6 H1O6 0.839(10) 2_655 ?

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 Cu1 N2 172.33(8) . . ?
N1 Cu1 O1 81.15(7) . . ?
N2 Cu1 O1 96.55(7) . . ?
N1 Cu1 O3 80.24(7) . . ?
N2 Cu1 O3 101.84(7) . . ?
O1 Cu1 O3 161.39(6) . . ?
N1 Cu1 O5 88.59(7) . . ?
N2 Cu1 O5 98.93(7) . . ?
O1 Cu1 O5 95.11(7) . . ?
O3 Cu1 O5 84.89(6) . . ?
C1 O1 Cu1 114.92(13) . . ?
C7 O3 Cu1 114.35(13) . . ?
C2 N1 C6 123.32(18) . . ?
C2 N1 Cu1 117.70(14) . . ?
C6 N1 Cu1 118.98(15) . . ?
C12 N2 C8 117.75(18) . . ?
C12 N2 Cu1 122.38(13) . . ?
C8 N2 Cu1 119.85(15) . . ?
O2 C1 O1 126.6(2) . . ?
O2 C1 C2 119.55(19) . . ?
O1 C1 C2 113.82(18) . . ?
N1 C2 C3 120.04(19) . . ?
N1 C2 C1 112.02(18) . . ?
C3 C2 C1 127.9(2) . . ?
C2 C3 C4 117.9(2) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.1 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 118.0(2) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
N1 C6 C5 119.8(2) . . ?
N1 C6 C7 112.02(18) . . ?
C5 C6 C7 128.20(19) . . ?
O4 C7 O3 125.9(2) . . ?
O4 C7 C6 119.70(18) . . ?
O3 C7 C6 114.35(17) . . ?
N2 C8 C9 122.5(2) . . ?
N2 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
C8 C9 C10 119.90(19) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 116.89(18) . . ?
C11 C10 C10 121.6(2) . 7_656 ?
C9 C10 C10 121.5(2) . 7_656 ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
N2 C12 C11 122.81(19) . . ?
N2 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
Cu1 O5 H1O5 102(2) . . ?
Cu1 O5 H2O5 110(2) . . ?
H1O5 O5 H2O5 109(2) . . ?
H1O6 O6 H1O6 95(5) . 2_655 ?

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 O1 C1 O2 -171.6(2) . . . . ?
Cu1 O1 C1 C2 6.7(2) . . . . ?
C6 N1 C2 C3 1.3(3) . . . . ?
Cu1 N1 C2 C3 -178.42(16) . . . . ?
C6 N1 C2 C1 -177.04(19) . . . . ?
Cu1 N1 C2 C1 3.2(2) . . . . ?
O2 C1 C2 N1 171.9(2) . . . . ?
O1 C1 C2 N1 -6.5(3) . . . . ?
O2 C1 C2 C3 -6.3(4) . . . . ?
O1 C1 C2 C3 175.3(2) . . . . ?
N1 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 C4 177.7(2) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C2 N1 C6 C5 -1.2(3) . . . . ?
Cu1 N1 C6 C5 178.48(16) . . . . ?
C2 N1 C6 C7 179.01(18) . . . . ?
Cu1 N1 C6 C7 -1.3(2) . . . . ?
C4 C5 C6 N1 0.2(3) . . . . ?
C4 C5 C6 C7 179.9(2) . . . . ?
Cu1 O3 C7 O4 178.05(19) . . . . ?
Cu1 O3 C7 C6 -2.9(2) . . . . ?
N1 C6 C7 O4 -178.1(2) . . . . ?
C5 C6 C7 O4 2.2(4) . . . . ?
N1 C6 C7 O3 2.8(3) . . . . ?
C5 C6 C7 O3 -177.0(2) . . . . ?
C12 N2 C8 C9 1.2(3) . . . . ?
Cu1 N2 C8 C9 -177.19(18) . . . . ?
N2 C8 C9 C10 0.4(4) . . . . ?
C8 C9 C10 C11 -1.5(3) . . . . ?
C8 C9 C10 C10 177.8(2) . . . 7_656 ?
C9 C10 C11 C12 1.2(3) . . . . ?
C10 C10 C11 C12 -178.2(2) 7_656 . . . ?
C8 N2 C12 C11 -1.6(3) . . . . ?
Cu1 N2 C12 C11 176.77(17) . . . . ?
C10 C11 C12 N2 0.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H1O5 O3 0.829(10) 1.935(11) 2.762(2) 175(3) 1_565 yes
O5 H2O5 O6 0.825(10) 2.216(16) 2.9812(17) 154(3) 1_565 yes
O6 H1O6 O4 0.839(10) 1.976(11) 2.812(3) 174(4) . yes

_refine_diff_density_max         0.602
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_SPA225
_database_code_depnum_ccdc_archive 'CCDC 1889370'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2019-06-24 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         'C12 H8 Cu N2 O4'
_chemical_formula_sum            'C12 H8 Cu N2 O4'
_chemical_formula_weight         307.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0018 0.0011 '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 0.0038 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0071 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3362 0.9389 '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                   7.8977(16)
_cell_length_b                   13.599(3)
_cell_length_c                   10.051(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.65(3)
_cell_angle_gamma                90
_cell_volume                     1079.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    17243
_cell_measurement_theta_min      0.344
_cell_measurement_theta_max      33.749

_exptl_crystal_description       block
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    1.285
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.920
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.600
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5625
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.010
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_full        21.100
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             1555
_reflns_number_gt                1471
_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       
'PAL BL2D-SMDC Program(Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.6'
_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)+(0.0594P)²+0.4434P] 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       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1555
_refine_ls_number_parameters     90
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.56489(2) 0.750000 0.01467(12) Uani 1 2 d S T P . .
O1 O 0.34720(13) 0.54184(8) 0.58965(10) 0.0173(2) Uani 1 1 d . . . . .
O2 O 0.26662(15) 0.42061(8) 0.44961(11) 0.0216(2) Uani 1 1 d . . . . .
N1 N 0.500000 0.42528(12) 0.750000 0.0132(3) Uani 1 2 d S T P . .
C1 C 0.33416(17) 0.45119(10) 0.55332(13) 0.0149(2) Uani 1 1 d . . . . .
C2 C 0.41642(16) 0.37906(10) 0.65133(13) 0.0140(2) Uani 1 1 d . . . . .
C3 C 0.41345(18) 0.27752(11) 0.64845(14) 0.0179(3) Uani 1 1 d . . . . .
H3 H 0.354166 0.243130 0.579289 0.022 Uiso 1 1 calc R U . . .
C4 C 0.500000 0.22712(15) 0.750000 0.0205(4) Uani 1 2 d S T P . .
H4 H 0.500000 0.157258 0.750001 0.025 Uiso 1 2 calc R U P . .
N2 N 0.500000 0.70822(12) 0.750000 0.0143(3) Uani 1 2 d S T P . .
C5 C 0.42452(19) 0.75883(11) 0.64964(14) 0.0187(3) Uani 1 1 d . . . . .
H5 H 0.370688 0.723336 0.578849 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4223(2) 0.86024(12) 0.64557(17) 0.0246(3) Uani 1 1 d . . . . .
H6 H 0.368896 0.894157 0.573158 0.030 Uiso 1 1 calc R U . . .
C7 C 0.500000 0.91137(18) 0.750000 0.0253(4) Uani 1 2 d S T P . .
H7 H 0.500001 0.981228 0.749999 0.030 Uiso 1 2 calc R U P . .


_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 N1 1.8986(16) . ?
Cu1 N2 1.9491(17) . ?
Cu1 O1 2.0100(11) . ?
Cu1 O1 2.0100(11) 2_656 ?
O1 C1 1.2890(17) . ?
O2 C1 1.2296(18) . ?
N1 C2 1.3329(15) . ?
N1 C2 1.3329(15) 2_656 ?
C1 C2 1.5223(19) . ?
C2 C3 1.381(2) . ?
C3 C4 1.3924(18) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
N2 C5 1.3460(16) 2_656 ?
N2 C5 1.3461(16) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(2) . ?
C6 H6 0.9500 . ?
C7 H7 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
N1 Cu1 N2 180.0 . . ?
N1 Cu1 O1 81.03(3) . . ?
N2 Cu1 O1 98.97(3) . . ?
N1 Cu1 O1 81.03(3) . 2_656 ?
N2 Cu1 O1 98.97(3) . 2_656 ?
O1 Cu1 O1 162.06(6) . 2_656 ?
C1 O1 Cu1 114.67(9) . . ?
C2 N1 C2 123.73(17) . 2_656 ?
C2 N1 Cu1 118.13(8) . . ?
C2 N1 Cu1 118.13(8) 2_656 . ?
O2 C1 O1 126.35(14) . . ?
O2 C1 C2 119.82(13) . . ?
O1 C1 C2 113.82(12) . . ?
N1 C2 C3 119.65(14) . . ?
N1 C2 C1 111.75(12) . . ?
C3 C2 C1 128.60(13) . . ?
C2 C3 C4 117.98(14) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C3 C4 C3 121.01(19) . 2_656 ?
C3 C4 H4 119.5 . . ?
C3 C4 H4 119.5 2_656 . ?
C5 N2 C5 118.50(17) 2_656 . ?
C5 N2 Cu1 120.75(9) 2_656 . ?
C5 N2 Cu1 120.75(9) . . ?
N2 C5 C6 122.57(15) . . ?
N2 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C7 118.26(17) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C6 C7 C6 119.8(2) 2_656 . ?
C6 C7 H7 120.1 2_656 . ?
C6 C7 H7 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 N1 C2 3.26(7) . . . . ?
O1 Cu1 N1 C2 -176.74(7) 2_656 . . . ?
O1 Cu1 N1 C2 -176.74(7) . . . 2_656 ?
O1 Cu1 N1 C2 3.26(7) 2_656 . . 2_656 ?
Cu1 O1 C1 O2 -170.02(12) . . . . ?
Cu1 O1 C1 C2 8.53(14) . . . . ?
C2 N1 C2 C3 0.17(9) 2_656 . . . ?
Cu1 N1 C2 C3 -179.83(9) . . . . ?
C2 N1 C2 C1 -179.80(11) 2_656 . . . ?
Cu1 N1 C2 C1 0.21(11) . . . . ?
O2 C1 C2 N1 172.75(12) . . . . ?
O1 C1 C2 N1 -5.91(15) . . . . ?
O2 C1 C2 C3 -7.2(2) . . . . ?
O1 C1 C2 C3 174.13(13) . . . . ?
N1 C2 C3 C4 -0.32(18) . . . . ?
C1 C2 C3 C4 179.63(11) . . . . ?
C2 C3 C4 C3 0.16(9) . . . 2_656 ?
C5 N2 C5 C6 0.28(11) 2_656 . . . ?
Cu1 N2 C5 C6 -179.72(11) . . . . ?
N2 C5 C6 C7 -0.5(2) . . . . ?
C5 C6 C7 C6 0.25(10) . . . 2_656 ?

_refine_diff_density_max         0.691
_refine_diff_density_min         -0.977
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_SPA224
_database_code_depnum_ccdc_archive 'CCDC 1889369'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2019-06-24 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 N O5'
_chemical_formula_sum            'C7 H5 Cu N O5'
_chemical_formula_weight         246.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0018 0.0011 '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 0.0038 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0071 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3362 0.9389 '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                   12.072(2)
_cell_length_b                   10.473(2)
_cell_length_c                   7.6968(15)
_cell_angle_alpha                90
_cell_angle_beta                 127.27(3)
_cell_angle_gamma                90
_cell_volume                     774.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    26599
_cell_measurement_theta_min      0.344
_cell_measurement_theta_max      33.749

_exptl_crystal_description       block
_exptl_crystal_colour            'deep blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.116
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    1.772
_shelx_estimated_absorpt_T_min   0.879
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.600
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4093
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.429
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        21.100
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             1102
_reflns_number_gt                1030
_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       
'PAL BL2D-SMDC Program(Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.6'
_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)+(0.0759P)²+0.3071P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.069(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1102
_refine_ls_number_parameters     70
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.83472(3) 0.750000 0.02396(19) Uani 1 2 d S T P . .
O1 O 0.33423(15) 0.80351(16) 0.7481(3) 0.0285(3) Uani 1 1 d . . . . .
O2 O 0.18498(18) 0.64710(17) 0.6766(3) 0.0347(4) Uani 1 1 d . . . . .
O3 O 0.500000 1.0201(3) 0.750000 0.0522(8) Uani 1 2 d DS T P . .
H1O3 H 0.561(3) 1.0661(17) 0.760(7) 0.063 Uiso 1 1 d D U . . .
N1 N 0.500000 0.6533(2) 0.750000 0.0214(5) Uani 1 2 d S T P . .
C1 C 0.2950(2) 0.6863(2) 0.7181(4) 0.0259(4) Uani 1 1 d . . . . .
C2 C 0.39605(18) 0.59265(19) 0.7314(3) 0.0221(3) Uani 1 1 d . . . . .
C3 C 0.39175(19) 0.4605(2) 0.7290(3) 0.0261(4) Uani 1 1 d . . . . .
H3 H 0.317637 0.416080 0.713596 0.031 Uiso 1 1 calc R U . . .
C4 C 0.500000 0.3945(3) 0.750000 0.0270(5) Uani 1 2 d S T P . .
H4 H 0.499999 0.303819 0.749999 0.032 Uiso 1 2 calc R U P . .


_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 N1 1.900(2) . ?
Cu1 O3 1.941(3) . ?
Cu1 O1 2.0188(14) . ?
Cu1 O1 2.0188(14) 2_656 ?
O1 C1 1.286(3) . ?
O2 C1 1.233(3) . ?
O3 H1O3 0.841(7) . ?
O3 H1O3 0.841(7) 2_656 ?
N1 C2 1.335(2) . ?
N1 C2 1.335(2) 2_656 ?
C1 C2 1.519(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.398(2) . ?
C3 H3 0.9500 . ?
C4 H4 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
N1 Cu1 O3 180.0 . . ?
N1 Cu1 O1 80.68(5) . . ?
O3 Cu1 O1 99.32(5) . . ?
N1 Cu1 O1 80.68(5) . 2_656 ?
O3 Cu1 O1 99.32(5) . 2_656 ?
O1 Cu1 O1 161.36(10) . 2_656 ?
C1 O1 Cu1 114.31(13) . . ?
Cu1 O3 H1O3 125.0(13) . . ?
Cu1 O3 H1O3 125.0(13) . 2_656 ?
H1O3 O3 H1O3 110(3) . 2_656 ?
C2 N1 C2 123.1(2) . 2_656 ?
C2 N1 Cu1 118.43(12) . . ?
C2 N1 Cu1 118.43(12) 2_656 . ?
O2 C1 O1 125.9(2) . . ?
O2 C1 C2 119.8(2) . . ?
O1 C1 C2 114.26(17) . . ?
N1 C2 C3 120.16(17) . . ?
N1 C2 C1 111.37(18) . . ?
C3 C2 C1 128.47(16) . . ?
C2 C3 C4 117.87(18) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C3 C4 C3 120.8(3) 2_656 . ?
C3 C4 H4 119.6 2_656 . ?
C3 C4 H4 119.6 . . ?

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 O1 C1 O2 -167.86(19) . . . . ?
Cu1 O1 C1 C2 10.5(2) . . . . ?
C2 N1 C2 C3 -0.51(13) 2_656 . . . ?
Cu1 N1 C2 C3 179.49(13) . . . . ?
C2 N1 C2 C1 178.73(16) 2_656 . . . ?
Cu1 N1 C2 C1 -1.27(16) . . . . ?
O2 C1 C2 N1 172.11(18) . . . . ?
O1 C1 C2 N1 -6.4(2) . . . . ?
O2 C1 C2 C3 -8.7(3) . . . . ?
O1 C1 C2 C3 172.79(19) . . . . ?
N1 C2 C3 C4 1.0(2) . . . . ?
C1 C2 C3 C4 -178.12(16) . . . . ?
C2 C3 C4 C3 -0.48(12) . . . 2_656 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H1O3 O2 0.841(7) 2.132(15) 2.933(2) 159(4) 3 yes

_refine_diff_density_max         0.677
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.127

####################################################################### 
# 
# 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_SPA222
_database_code_depnum_ccdc_archive 'CCDC 1889368'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2019-06-24 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         'C68 H44 Cu6 N12 O16'
_chemical_formula_sum            'C68 H44 Cu6 N12 O16'
_chemical_formula_weight         1666.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3383 1.0252 '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                   41.526(8)
_cell_length_b                   10.852(2)
_cell_length_c                   13.786(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.84(3)
_cell_angle_gamma                90
_cell_volume                     6180(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    72668
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_F_000             3352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.011
_exptl_absorpt_coefficient_mu    1.522
_shelx_estimated_absorpt_T_min   0.850
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31116
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -58
_diffrn_reflns_limit_h_max       58
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.118
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9158
_reflns_number_gt                6860
_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       
'PAL BL2D-SMDC Program(Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.6'
_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)+(0.0762P)²] 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       0.00199(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9158
_refine_ls_number_parameters     470
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      2.999
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1A Cu 0.37353(2) 0.79560(3) 0.64219(2) 0.01722(9) Uani 1 1 d . . . . .
O1A O 0.39743(5) 0.91601(16) 0.55323(14) 0.0236(4) Uani 1 1 d . . . . .
O2A O 0.41172(5) 1.11600(19) 0.54749(17) 0.0358(5) Uani 1 1 d . . . . .
O3A O 0.34885(5) 0.73780(17) 0.76092(15) 0.0278(4) Uani 1 1 d . . . . .
O4A O 0.33040(5) 0.81145(18) 0.89644(16) 0.0296(4) Uani 1 1 d . . . . .
O5A O 0.41875(5) 0.71232(17) 0.71170(17) 0.0316(5) Uani 1 1 d . . . . .
O6A O 0.44507(5) 0.53294(19) 0.71584(17) 0.0365(5) Uani 1 1 d . . . . .
O7A O 0.32626(4) 0.79257(14) 0.53764(14) 0.0206(4) Uani 1 1 d . . . . .
O8A O 0.30553(5) 0.68446(17) 0.40746(15) 0.0274(4) Uani 1 1 d . . . . .
N1A N 0.37132(5) 0.94668(18) 0.71352(15) 0.0150(4) Uani 1 1 d . . . . .
N2A N 0.37518(5) 0.63745(17) 0.57251(16) 0.0169(4) Uani 1 1 d . . . . .
C1A C 0.39915(6) 1.0267(2) 0.58390(19) 0.0201(5) Uani 1 1 d . . . . .
C2A C 0.38419(5) 1.0471(2) 0.67828(18) 0.0163(4) Uani 1 1 d . . . . .
C3A C 0.38304(7) 1.1584(2) 0.7272(2) 0.0279(6) Uani 1 1 d . . . . .
H3A H 0.391871 1.231068 0.702080 0.033 Uiso 1 1 calc R U . . .
C4A C 0.36859(8) 1.1611(3) 0.8144(2) 0.0344(7) Uani 1 1 d . . . . .
H4A H 0.367919 1.235857 0.849986 0.041 Uiso 1 1 calc R U . . .
C5A C 0.35524(7) 1.0547(3) 0.8490(2) 0.0268(6) Uani 1 1 d . . . . .
H5A H 0.345023 1.055625 0.907587 0.032 Uiso 1 1 calc R U . . .
C6A C 0.35715(5) 0.9473(2) 0.79614(18) 0.0177(4) Uani 1 1 d . . . . .
C7A C 0.34405(6) 0.8219(2) 0.8220(2) 0.0211(5) Uani 1 1 d . . . . .
C8A C 0.42288(6) 0.6048(2) 0.6835(2) 0.0228(5) Uani 1 1 d . . . . .
C9A C 0.39903(6) 0.5581(2) 0.6016(2) 0.0222(5) Uani 1 1 d . . . . .
C10A C 0.40059(7) 0.4433(2) 0.5572(3) 0.0358(7) Uani 1 1 d . . . . .
H10A H 0.417250 0.386606 0.578624 0.043 Uiso 1 1 calc R U . . .
C11A C 0.37749(8) 0.4129(3) 0.4813(3) 0.0480(10) Uani 1 1 d . . . . .
H11A H 0.378320 0.335430 0.449587 0.058 Uiso 1 1 calc R U . . .
C12A C 0.35318(7) 0.4963(3) 0.4520(3) 0.0390(8) Uani 1 1 d . . . . .
H12A H 0.337351 0.477167 0.399451 0.047 Uiso 1 1 calc R U . . .
C13A C 0.35225(6) 0.6079(2) 0.5001(2) 0.0197(5) Uani 1 1 d . . . . .
C14A C 0.32553(6) 0.7032(2) 0.47859(19) 0.0174(4) Uani 1 1 d . . . . .
Cu2B Cu 0.47872(2) 0.57548(3) 0.84674(3) 0.02721(10) Uani 1 1 d . . . . .
N1B N 0.48309(5) 0.74943(18) 0.86852(15) 0.0200(4) Uani 1 1 d . . . . .
N2B N 0.48231(6) 1.40233(19) 0.87746(18) 0.0238(5) Uani 1 1 d . . . . .
C1B C 0.51074(6) 0.8127(2) 0.8649(2) 0.0220(5) Uani 1 1 d . . . . .
H1B H 0.530070 0.768493 0.857242 0.026 Uiso 1 1 calc R U . . .
C2B C 0.51211(6) 0.9393(2) 0.87200(19) 0.0197(5) Uani 1 1 d . . . . .
H2B H 0.532136 0.980591 0.868608 0.024 Uiso 1 1 calc R U . . .
C3B C 0.48431(6) 1.00712(19) 0.88410(17) 0.0146(4) Uani 1 1 d . . . . .
C4B C 0.45610(6) 0.9405(2) 0.89147(18) 0.0177(4) Uani 1 1 d . . . . .
H4B H 0.436578 0.982207 0.901258 0.021 Uiso 1 1 calc R U . . .
C5B C 0.45651(6) 0.8133(2) 0.88454(19) 0.0213(5) Uani 1 1 d . . . . .
H5B H 0.437090 0.769337 0.891435 0.026 Uiso 1 1 calc R U . . .
C6B C 0.45593(7) 1.3363(2) 0.8923(3) 0.0375(8) Uani 1 1 d . . . . .
H6B H 0.436290 1.378968 0.898848 0.045 Uiso 1 1 calc R U . . .
C7B C 0.45601(7) 1.2093(2) 0.8986(3) 0.0341(7) Uani 1 1 d . . . . .
H7B H 0.436825 1.166867 0.910773 0.041 Uiso 1 1 calc R U . . .
C8B C 0.48407(6) 1.1435(2) 0.88719(17) 0.0150(4) Uani 1 1 d . . . . .
C9B C 0.51168(6) 1.2127(2) 0.8764(2) 0.0214(5) Uani 1 1 d . . . . .
H9B H 0.531854 1.172876 0.872210 0.026 Uiso 1 1 calc R U . . .
C10B C 0.50961(7) 1.3402(2) 0.8718(2) 0.0251(5) Uani 1 1 d . . . . .
H10B H 0.528767 1.385479 0.864285 0.030 Uiso 1 1 calc R U . . .
Cu3C Cu 0.27401(2) 0.79825(3) 0.61985(3) 0.02339(11) Uani 0.8 1 d . U P A 1
Cu4C Cu 0.25943(4) 0.79867(14) 0.61811(12) 0.0179(3) Uani 0.2 1 d . U P A 2
N1C N 0.26980(6) 0.62514(18) 0.63328(17) 0.0258(5) Uani 1 1 d . . . . .
N2C N 0.27054(6) -0.02737(18) 0.62047(16) 0.0233(5) Uani 1 1 d . . . . .
C1C C 0.29681(7) 0.5599(2) 0.6564(2) 0.0280(6) Uani 1 1 d . . . . .
H1C H 0.316491 0.603088 0.673248 0.034 Uiso 1 1 calc R U . . .
C2C C 0.29739(6) 0.4327(2) 0.6569(2) 0.0245(5) Uani 1 1 d . . . . .
H2C H 0.317228 0.390237 0.672932 0.029 Uiso 1 1 calc R U . . .
C3C C 0.26885(5) 0.36674(19) 0.63397(17) 0.0146(4) Uani 1 1 d . . . . .
C4C C 0.24034(6) 0.4343(2) 0.61482(18) 0.0185(5) Uani 1 1 d . . . . .
H4C H 0.220132 0.393353 0.601906 0.022 Uiso 1 1 calc R U . . .
C5C C 0.24185(7) 0.5625(2) 0.61486(19) 0.0234(5) Uani 1 1 d . . . . .
H5C H 0.222322 0.607777 0.601306 0.028 Uiso 1 1 calc R U . . .
C6C C 0.29684(7) 0.0400(2) 0.6080(2) 0.0250(5) Uani 1 1 d . . . . .
H6C H 0.316169 -0.001738 0.596139 0.030 Uiso 1 1 calc R U . . .
C7C C 0.29721(6) 0.1669(2) 0.6115(2) 0.0219(5) Uani 1 1 d . . . . .
H7C H 0.316494 0.210825 0.602724 0.026 Uiso 1 1 calc R U . . .
C8C C 0.26906(5) 0.23062(19) 0.62809(17) 0.0147(4) Uani 1 1 d . . . . .
C9C C 0.24121(6) 0.1612(2) 0.63683(18) 0.0183(5) Uani 1 1 d . . . . .
H9C H 0.221240 0.200764 0.644801 0.022 Uiso 1 1 calc R U . . .
C10C C 0.24310(7) 0.0336(2) 0.63372(19) 0.0241(5) Uani 1 1 d . . . . .
H10C H 0.224131 -0.012867 0.641297 0.029 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
Cu1A N1A 1.919(2) . ?
Cu1A N2A 1.971(2) . ?
Cu1A O1A 2.1081(19) . ?
Cu1A O3A 2.113(2) . ?
Cu1A O5A 2.213(2) . ?
Cu1A O7A 2.315(2) . ?
O1A C1A 1.273(3) . ?
O2A C1A 1.232(3) . ?
O3A C7A 1.271(3) . ?
O4A C7A 1.228(3) . ?
O5A C8A 1.247(3) . ?
O6A C8A 1.254(3) . ?
O6A Cu2B 2.216(2) . ?
O7A C14A 1.265(3) . ?
O8A C14A 1.236(3) . ?
N1A C2A 1.328(3) . ?
N1A C6A 1.334(3) . ?
N2A C9A 1.343(3) . ?
N2A C13A 1.346(3) . ?
C1A C2A 1.514(3) . ?
C2A C3A 1.386(3) . ?
C3A C4A 1.397(4) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.386(4) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.381(4) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.521(3) . ?
C8A C9A 1.512(4) . ?
C9A C10A 1.392(4) . ?
C10A C11A 1.385(4) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.386(4) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.383(3) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.523(3) . ?
Cu2B N1B 1.917(2) . ?
Cu2B N2B 1.929(2) 1_545 ?
N1B C5B 1.341(3) . ?
N1B C1B 1.343(3) . ?
N2B C10B 1.328(3) . ?
N2B C6B 1.342(4) . ?
C1B C2B 1.378(3) . ?
C1B H1B 0.9500 . ?
C2B C3B 1.393(3) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.389(3) . ?
C3B C8B 1.481(3) . ?
C4B C5B 1.384(3) . ?
C4B H4B 0.9500 . ?
C5B H5B 0.9500 . ?
C6B C7B 1.381(3) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.389(3) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.391(3) . ?
C9B C10B 1.386(3) . ?
C9B H9B 0.9500 . ?
C10B H10B 0.9500 . ?
Cu3C N1C 1.898(2) . ?
Cu3C N2C 1.898(2) 1_565 ?
Cu4C N1C 1.938(3) . ?
Cu4C N2C 1.943(3) 1_565 ?
N1C C1C 1.337(4) . ?
N1C C5C 1.347(4) . ?
N2C C6C 1.340(4) . ?
N2C C10C 1.346(4) . ?
C1C C2C 1.381(3) . ?
C1C H1C 0.9500 . ?
C2C C3C 1.393(3) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.395(3) . ?
C3C C8C 1.479(3) . ?
C4C C5C 1.393(3) . ?
C4C H4C 0.9500 . ?
C5C H5C 0.9500 . ?
C6C C7C 1.378(3) . ?
C6C H6C 0.9500 . ?
C7C C8C 1.397(3) . ?
C7C H7C 0.9500 . ?
C8C C9C 1.396(3) . ?
C9C C10C 1.388(3) . ?
C9C H9C 0.9500 . ?
C10C H10C 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
N1A Cu1A N2A 178.07(9) . . ?
N1A Cu1A O1A 79.54(8) . . ?
N2A Cu1A O1A 102.38(8) . . ?
N1A Cu1A O3A 78.72(8) . . ?
N2A Cu1A O3A 99.36(8) . . ?
O1A Cu1A O3A 158.26(7) . . ?
N1A Cu1A O5A 102.11(8) . . ?
N2A Cu1A O5A 77.61(8) . . ?
O1A Cu1A O5A 94.37(8) . . ?
O3A Cu1A O5A 90.03(9) . . ?
N1A Cu1A O7A 104.45(7) . . ?
N2A Cu1A O7A 75.73(7) . . ?
O1A Cu1A O7A 93.79(7) . . ?
O3A Cu1A O7A 91.75(8) . . ?
O5A Cu1A O7A 153.21(6) . . ?
C1A O1A Cu1A 113.91(16) . . ?
C7A O3A Cu1A 114.88(16) . . ?
C8A O5A Cu1A 112.61(17) . . ?
C8A O6A Cu2B 122.67(18) . . ?
C14A O7A Cu1A 112.02(15) . . ?
C2A N1A C6A 122.5(2) . . ?
C2A N1A Cu1A 118.17(16) . . ?
C6A N1A Cu1A 119.36(17) . . ?
C9A N2A C13A 120.9(2) . . ?
C9A N2A Cu1A 118.32(17) . . ?
C13A N2A Cu1A 120.75(15) . . ?
O2A C1A O1A 128.2(2) . . ?
O2A C1A C2A 117.6(2) . . ?
O1A C1A C2A 114.2(2) . . ?
N1A C2A C3A 120.1(2) . . ?
N1A C2A C1A 114.2(2) . . ?
C3A C2A C1A 125.7(2) . . ?
C2A C3A C4A 118.4(3) . . ?
C2A C3A H3A 120.8 . . ?
C4A C3A H3A 120.8 . . ?
C5A C4A C3A 120.0(3) . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C6A C5A C4A 118.4(3) . . ?
C6A C5A H5A 120.8 . . ?
C4A C5A H5A 120.8 . . ?
N1A C6A C5A 120.6(2) . . ?
N1A C6A C7A 113.2(2) . . ?
C5A C6A C7A 126.2(2) . . ?
O4A C7A O3A 127.2(2) . . ?
O4A C7A C6A 119.0(2) . . ?
O3A C7A C6A 113.8(2) . . ?
O5A C8A O6A 126.2(3) . . ?
O5A C8A C9A 116.5(2) . . ?
O6A C8A C9A 117.3(2) . . ?
N2A C9A C10A 120.6(2) . . ?
N2A C9A C8A 114.5(2) . . ?
C10A C9A C8A 124.9(2) . . ?
C11A C10A C9A 119.0(3) . . ?
C11A C10A H10A 120.5 . . ?
C9A C10A H10A 120.5 . . ?
C10A C11A C12A 119.5(3) . . ?
C10A C11A H11A 120.2 . . ?
C12A C11A H11A 120.2 . . ?
C13A C12A C11A 119.1(3) . . ?
C13A C12A H12A 120.4 . . ?
C11A C12A H12A 120.4 . . ?
N2A C13A C12A 120.8(2) . . ?
N2A C13A C14A 115.4(2) . . ?
C12A C13A C14A 123.8(2) . . ?
O8A C14A O7A 127.4(2) . . ?
O8A C14A C13A 117.4(2) . . ?
O7A C14A C13A 115.2(2) . . ?
N1B Cu2B N2B 157.08(10) . 1_545 ?
N1B Cu2B O6A 111.99(8) . . ?
N2B Cu2B O6A 90.23(9) 1_545 . ?
C5B N1B C1B 117.6(2) . . ?
C5B N1B Cu2B 117.95(17) . . ?
C1B N1B Cu2B 124.40(18) . . ?
C10B N2B C6B 116.9(2) . . ?
C10B N2B Cu2B 121.96(18) . 1_565 ?
C6B N2B Cu2B 120.51(18) . 1_565 ?
N1B C1B C2B 122.4(2) . . ?
N1B C1B H1B 118.8 . . ?
C2B C1B H1B 118.8 . . ?
C1B C2B C3B 120.4(2) . . ?
C1B C2B H2B 119.8 . . ?
C3B C2B H2B 119.8 . . ?
C4B C3B C2B 116.7(2) . . ?
C4B C3B C8B 120.7(2) . . ?
C2B C3B C8B 122.6(2) . . ?
C5B C4B C3B 119.9(2) . . ?
C5B C4B H4B 120.1 . . ?
C3B C4B H4B 120.1 . . ?
N1B C5B C4B 122.9(2) . . ?
N1B C5B H5B 118.6 . . ?
C4B C5B H5B 118.6 . . ?
N2B C6B C7B 123.1(3) . . ?
N2B C6B H6B 118.5 . . ?
C7B C6B H6B 118.5 . . ?
C6B C7B C8B 120.2(3) . . ?
C6B C7B H7B 119.9 . . ?
C8B C7B H7B 119.9 . . ?
C7B C8B C9B 116.4(2) . . ?
C7B C8B C3B 121.7(2) . . ?
C9B C8B C3B 121.9(2) . . ?
C10B C9B C8B 119.7(2) . . ?
C10B C9B H9B 120.2 . . ?
C8B C9B H9B 120.2 . . ?
N2B C10B C9B 123.6(2) . . ?
N2B C10B H10B 118.2 . . ?
C9B C10B H10B 118.2 . . ?
N1C Cu3C N2C 168.20(11) . 1_565 ?
N1C Cu4C N2C 153.19(15) . 1_565 ?
C1C N1C C5C 117.7(2) . . ?
C1C N1C Cu3C 117.63(19) . . ?
C5C N1C Cu3C 124.56(19) . . ?
C1C N1C Cu4C 135.4(2) . . ?
C5C N1C Cu4C 106.98(19) . . ?
C6C N2C C10C 117.5(2) . . ?
C6C N2C Cu3C 118.69(18) . 1_545 ?
C10C N2C Cu3C 123.82(18) . 1_545 ?
C6C N2C Cu4C 136.3(2) . 1_545 ?
C10C N2C Cu4C 106.09(18) . 1_545 ?
Cu3C N2C Cu4C 18.04(5) 1_545 1_545 ?
N1C C1C C2C 123.0(3) . . ?
N1C C1C H1C 118.5 . . ?
C2C C1C H1C 118.5 . . ?
C1C C2C C3C 119.9(3) . . ?
C1C C2C H2C 120.0 . . ?
C3C C2C H2C 120.0 . . ?
C2C C3C C4C 117.3(2) . . ?
C2C C3C C8C 121.1(2) . . ?
C4C C3C C8C 121.6(2) . . ?
C5C C4C C3C 119.2(2) . . ?
C5C C4C H4C 120.4 . . ?
C3C C4C H4C 120.4 . . ?
N1C C5C C4C 122.8(2) . . ?
N1C C5C H5C 118.6 . . ?
C4C C5C H5C 118.6 . . ?
N2C C6C C7C 123.2(2) . . ?
N2C C6C H6C 118.4 . . ?
C7C C6C H6C 118.4 . . ?
C6C C7C C8C 119.6(2) . . ?
C6C C7C H7C 120.2 . . ?
C8C C7C H7C 120.2 . . ?
C9C C8C C7C 117.5(2) . . ?
C9C C8C C3C 121.6(2) . . ?
C7C C8C C3C 120.8(2) . . ?
C10C C9C C8C 119.1(2) . . ?
C10C C9C H9C 120.5 . . ?
C8C C9C H9C 120.5 . . ?
N2C C10C C9C 123.1(2) . . ?
N2C C10C H10C 118.5 . . ?
C9C C10C H10C 118.5 . . ?

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
Cu1A O1A C1A O2A 179.6(2) . . . . ?
Cu1A O1A C1A C2A 1.0(3) . . . . ?
C6A N1A C2A C3A -0.4(4) . . . . ?
Cu1A N1A C2A C3A 179.8(2) . . . . ?
C6A N1A C2A C1A 179.9(2) . . . . ?
Cu1A N1A C2A C1A 0.1(3) . . . . ?
O2A C1A C2A N1A -179.5(2) . . . . ?
O1A C1A C2A N1A -0.7(3) . . . . ?
O2A C1A C2A C3A 0.8(4) . . . . ?
O1A C1A C2A C3A 179.6(3) . . . . ?
N1A C2A C3A C4A 1.0(4) . . . . ?
C1A C2A C3A C4A -179.3(3) . . . . ?
C2A C3A C4A C5A -1.3(5) . . . . ?
C3A C4A C5A C6A 1.1(5) . . . . ?
C2A N1A C6A C5A 0.1(4) . . . . ?
Cu1A N1A C6A C5A 179.95(19) . . . . ?
C2A N1A C6A C7A 179.8(2) . . . . ?
Cu1A N1A C6A C7A -0.4(3) . . . . ?
C4A C5A C6A N1A -0.5(4) . . . . ?
C4A C5A C6A C7A 180.0(3) . . . . ?
Cu1A O3A C7A O4A -179.9(2) . . . . ?
Cu1A O3A C7A C6A 0.2(3) . . . . ?
N1A C6A C7A O4A -179.8(2) . . . . ?
C5A C6A C7A O4A -0.2(4) . . . . ?
N1A C6A C7A O3A 0.1(3) . . . . ?
C5A C6A C7A O3A 179.8(3) . . . . ?
Cu1A O5A C8A O6A -174.4(3) . . . . ?
Cu1A O5A C8A C9A 6.4(3) . . . . ?
Cu2B O6A C8A O5A 8.4(4) . . . . ?
Cu2B O6A C8A C9A -172.44(18) . . . . ?
C13A N2A C9A C10A 0.1(4) . . . . ?
Cu1A N2A C9A C10A 177.6(2) . . . . ?
C13A N2A C9A C8A 179.9(2) . . . . ?
Cu1A N2A C9A C8A -2.6(3) . . . . ?
O5A C8A C9A N2A -3.1(4) . . . . ?
O6A C8A C9A N2A 177.7(3) . . . . ?
O5A C8A C9A C10A 176.7(3) . . . . ?
O6A C8A C9A C10A -2.6(4) . . . . ?
N2A C9A C10A C11A 1.1(5) . . . . ?
C8A C9A C10A C11A -178.6(3) . . . . ?
C9A C10A C11A C12A -0.8(6) . . . . ?
C10A C11A C12A C13A -0.8(6) . . . . ?
C9A N2A C13A C12A -1.8(4) . . . . ?
Cu1A N2A C13A C12A -179.2(2) . . . . ?
C9A N2A C13A C14A 176.5(2) . . . . ?
Cu1A N2A C13A C14A -0.9(3) . . . . ?
C11A C12A C13A N2A 2.2(5) . . . . ?
C11A C12A C13A C14A -176.0(3) . . . . ?
Cu1A O7A C14A O8A -171.2(2) . . . . ?
Cu1A O7A C14A C13A 10.0(2) . . . . ?
N2A C13A C14A O8A 174.1(2) . . . . ?
C12A C13A C14A O8A -7.6(4) . . . . ?
N2A C13A C14A O7A -6.9(3) . . . . ?
C12A C13A C14A O7A 171.3(3) . . . . ?
C5B N1B C1B C2B -3.4(4) . . . . ?
Cu2B N1B C1B C2B 173.8(2) . . . . ?
N1B C1B C2B C3B 0.5(4) . . . . ?
C1B C2B C3B C4B 1.9(4) . . . . ?
C1B C2B C3B C8B -176.9(2) . . . . ?
C2B C3B C4B C5B -1.4(4) . . . . ?
C8B C3B C4B C5B 177.4(2) . . . . ?
C1B N1B C5B C4B 4.0(4) . . . . ?
Cu2B N1B C5B C4B -173.4(2) . . . . ?
C3B C4B C5B N1B -1.6(4) . . . . ?
C10B N2B C6B C7B -2.1(5) . . . . ?
Cu2B N2B C6B C7B 169.0(3) 1_565 . . . ?
N2B C6B C7B C8B -1.5(6) . . . . ?
C6B C7B C8B C9B 4.4(5) . . . . ?
C6B C7B C8B C3B -174.1(3) . . . . ?
C4B C3B C8B C7B 0.8(4) . . . . ?
C2B C3B C8B C7B 179.5(3) . . . . ?
C4B C3B C8B C9B -177.6(2) . . . . ?
C2B C3B C8B C9B 1.1(4) . . . . ?
C7B C8B C9B C10B -3.7(4) . . . . ?
C3B C8B C9B C10B 174.7(2) . . . . ?
C6B N2B C10B C9B 2.8(5) . . . . ?
Cu2B N2B C10B C9B -168.2(2) 1_565 . . . ?
C8B C9B C10B N2B 0.2(4) . . . . ?
N2C Cu3C N1C C1C -138.1(5) 1_565 . . . ?
N2C Cu3C N1C C5C 46.5(6) 1_565 . . . ?
C5C N1C C1C C2C 3.6(4) . . . . ?
Cu3C N1C C1C C2C -172.1(2) . . . . ?
Cu4C N1C C1C C2C -176.4(2) . . . . ?
N1C C1C C2C C3C -0.9(5) . . . . ?
C1C C2C C3C C4C -2.4(4) . . . . ?
C1C C2C C3C C8C 176.2(3) . . . . ?
C2C C3C C4C C5C 3.0(4) . . . . ?
C8C C3C C4C C5C -175.6(2) . . . . ?
C1C N1C C5C C4C -2.9(4) . . . . ?
Cu3C N1C C5C C4C 172.48(19) . . . . ?
Cu4C N1C C5C C4C 177.1(2) . . . . ?
C3C C4C C5C N1C -0.4(4) . . . . ?
C10C N2C C6C C7C 2.3(4) . . . . ?
Cu3C N2C C6C C7C -177.1(2) 1_545 . . . ?
Cu4C N2C C6C C7C 178.1(2) 1_545 . . . ?
N2C C6C C7C C8C -0.5(4) . . . . ?
C6C C7C C8C C9C -2.3(4) . . . . ?
C6C C7C C8C C3C 178.9(2) . . . . ?
C2C C3C C8C C9C 158.9(3) . . . . ?
C4C C3C C8C C9C -22.5(4) . . . . ?
C2C C3C C8C C7C -22.4(4) . . . . ?
C4C C3C C8C C7C 156.2(2) . . . . ?
C7C C8C C9C C10C 3.2(4) . . . . ?
C3C C8C C9C C10C -178.0(2) . . . . ?
C6C N2C C10C C9C -1.3(4) . . . . ?
Cu3C N2C C10C C9C 178.0(2) 1_545 . . . ?
Cu4C N2C C10C C9C -178.3(2) 1_545 . . . ?
C8C C9C C10C N2C -1.5(4) . . . . ?

_refine_diff_density_max         1.991
_refine_diff_density_min         -1.949
_refine_diff_density_rms         0.114

####################################################################### 
# 
# 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_SPA227
_database_code_depnum_ccdc_archive 'CCDC 1889371'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2019-06-24 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         'C10 H11 Cu N2 O5, H2 0'
_chemical_formula_sum            'C10 H13 Cu N2 O6'
_chemical_formula_weight         320.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0018 0.0011 '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 0.0038 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0071 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3362 0.9389 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.4210(13)
_cell_length_b                   15.619(3)
_cell_length_c                   11.765(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.52(3)
_cell_angle_gamma                90
_cell_volume                     1166.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    69212
_cell_measurement_theta_min      0.35
_cell_measurement_theta_max      22.679

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.077
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    1.198
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.600
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11977
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.842
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        21.100
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3403
_reflns_number_gt                2768
_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       
'PAL BL2D-SMDC Program(Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.6'
_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)+(0.0485P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3403
_refine_ls_number_parameters     212
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0790
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.30548(3) 0.41183(2) 0.21678(2) 0.00950(9) Uani 1 1 d . . . . .
O1 O 0.5339(2) 0.50158(9) 0.23582(13) 0.0182(3) Uani 1 1 d . . . . .
O2 O 0.8182(2) 0.54244(10) 0.35724(14) 0.0221(3) Uani 1 1 d . . . . .
O3 O 0.0956(2) 0.32512(9) 0.26305(11) 0.0155(3) Uani 1 1 d . . . . .
O4 O 0.0453(2) 0.23630(11) 0.40520(13) 0.0247(4) Uani 1 1 d . . . . .
O5 O 0.4839(2) 0.31944(10) 0.12699(13) 0.0209(3) Uani 1 1 d D . . . .
H1O5 H 0.494(4) 0.3054(17) 0.0599(10) 0.031 Uiso 1 1 d D U . . .
H2O5 H 0.533(4) 0.2786(12) 0.1682(18) 0.031 Uiso 1 1 d D U . . .
N1 N 0.4372(2) 0.38501(10) 0.36926(13) 0.0100(3) Uani 1 1 d . . . . .
C1 C 0.6630(3) 0.49599(12) 0.32939(18) 0.0148(4) Uani 1 1 d . . . . .
C2 C 0.6122(3) 0.42738(12) 0.41064(16) 0.0117(3) Uani 1 1 d . . . . .
C3 C 0.7185(3) 0.40839(13) 0.51926(17) 0.0156(4) Uani 1 1 d . . . . .
H3 H 0.845928 0.436741 0.548929 0.019 Uiso 1 1 calc R U . . .
C4 C 0.6319(3) 0.34643(15) 0.58307(17) 0.0190(4) Uani 1 1 d . . . . .
H4 H 0.702290 0.331545 0.657233 0.023 Uiso 1 1 calc R U . . .
C5 C 0.4437(3) 0.30589(15) 0.53990(17) 0.0195(4) Uani 1 1 d . . . . .
H5 H 0.381297 0.265355 0.584769 0.023 Uiso 1 1 calc R U . . .
C6 C 0.3502(3) 0.32642(13) 0.42963(16) 0.0126(3) Uani 1 1 d . . . . .
C7 C 0.1463(3) 0.29223(13) 0.36226(16) 0.0147(4) Uani 1 1 d . . . . .
N2 N 0.1249(2) 0.46421(10) 0.08253(13) 0.0097(3) Uani 1 1 d . . . . .
C8 C 0.1322(6) 0.4221(2) -0.0247(3) 0.0140(7) Uani 0.5 1 d . . P A -1
H8A H 0.115045 0.359670 -0.015051 0.017 Uiso 0.5 1 calc R U P A -1
H8AB H 0.271165 0.432148 -0.049216 0.017 Uiso 0.5 1 calc R U P A -1
C9 C -0.0431(6) 0.4555(3) -0.1181(3) 0.0180(8) Uani 0.5 1 d . . P . .
H9A H 0.014030 0.463750 -0.190977 0.022 Uiso 0.5 1 calc R U P A .
H9AB H -0.158210 0.412893 -0.131640 0.022 Uiso 0.5 1 calc R U P . .
C10 C -0.1013(5) 0.4638(3) 0.1084(3) 0.0157(7) Uani 0.5 1 d . . P A -1
H10A H -0.104920 0.487618 0.186040 0.019 Uiso 0.5 1 calc R U P A -1
H10B H -0.154055 0.404173 0.107289 0.019 Uiso 0.5 1 calc R U P A -1
C11 C -0.2440(6) 0.5175(3) 0.0185(3) 0.0168(8) Uani 0.5 1 d . . P . .
H11A H -0.375440 0.485785 -0.008765 0.020 Uiso 0.5 1 calc R U P A .
H11B H -0.281786 0.571984 0.053291 0.020 Uiso 0.5 1 calc R U P . .
C12 C 0.1773(6) 0.5582(2) 0.0730(3) 0.0135(7) Uani 0.5 1 d . . P A -1
H12A H 0.329666 0.565066 0.070020 0.016 Uiso 0.5 1 calc R U P A -1
H12B H 0.143136 0.589411 0.141090 0.016 Uiso 0.5 1 calc R U P A -1
C13 C 0.0489(6) 0.5949(2) -0.0367(4) 0.0171(8) Uani 0.5 1 d . . P . .
H13A H -0.010474 0.651118 -0.019383 0.021 Uiso 0.5 1 calc R U P A .
H13B H 0.142315 0.603846 -0.095431 0.021 Uiso 0.5 1 calc R U P . .
O1W O 0.6561(2) 0.19421(10) 0.26940(14) 0.0202(3) Uani 1 1 d D . . . .
H1OW H 0.687(4) 0.1532(13) 0.229(2) 0.030 Uiso 1 1 d D U . . .
H2OW H 0.772(3) 0.2093(17) 0.307(2) 0.030 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.9128(16) . ?
Cu1 N2 1.9912(15) . ?
Cu1 O1 2.0169(14) . ?
Cu1 O3 2.0405(14) . ?
Cu1 O5 2.2068(15) . ?
O1 C1 1.279(2) . ?
O2 C1 1.237(2) . ?
O3 C7 1.273(2) . ?
O4 C7 1.239(2) . ?
O5 H1O5 0.831(10) . ?
O5 H2O5 0.835(10) . ?
N1 C6 1.331(2) . ?
N1 C2 1.333(2) . ?
C1 C2 1.504(3) . ?
C2 C3 1.389(3) . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.523(2) . ?
N2 C8 1.430(4) . ?
N2 C9 1.445(4) 3_565 ?
N2 C13 1.487(4) 3_565 ?
N2 C12 1.513(4) . ?
N2 C10 1.528(4) . ?
N2 C11 1.532(4) 3_565 ?
C8 C9 1.543(5) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C13 1.989(6) 3_565 ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C11 1.541(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.536(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
O1W H1OW 0.841(10) . ?
O1W H2OW 0.839(10) . ?

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 Cu1 N2 163.40(7) . . ?
N1 Cu1 O1 80.51(7) . . ?
N2 Cu1 O1 97.51(6) . . ?
N1 Cu1 O3 79.75(6) . . ?
N2 Cu1 O3 98.89(6) . . ?
O1 Cu1 O3 158.38(6) . . ?
N1 Cu1 O5 96.72(6) . . ?
N2 Cu1 O5 99.87(6) . . ?
O1 Cu1 O5 95.00(7) . . ?
O3 Cu1 O5 95.96(7) . . ?
C1 O1 Cu1 114.59(13) . . ?
C7 O3 Cu1 115.06(12) . . ?
Cu1 O5 H1O5 138.4(18) . . ?
Cu1 O5 H2O5 113.6(18) . . ?
H1O5 O5 H2O5 105.8(19) . . ?
C6 N1 C2 122.98(16) . . ?
C6 N1 Cu1 119.27(12) . . ?
C2 N1 Cu1 117.74(13) . . ?
O2 C1 O1 125.59(19) . . ?
O2 C1 C2 119.46(17) . . ?
O1 C1 C2 114.93(16) . . ?
N1 C2 C3 120.20(18) . . ?
N1 C2 C1 111.86(16) . . ?
C3 C2 C1 127.87(16) . . ?
C2 C3 C4 117.66(17) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C3 C4 C5 120.98(18) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 117.98(19) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
N1 C6 C5 120.09(17) . . ?
N1 C6 C7 111.09(16) . . ?
C5 C6 C7 128.80(18) . . ?
O4 C7 O3 125.48(17) . . ?
O4 C7 C6 119.76(17) . . ?
O3 C7 C6 114.76(16) . . ?
C8 N2 C9 135.7(2) . 3_565 ?
C8 N2 C13 61.0(2) . 3_565 ?
C9 N2 C13 111.0(3) 3_565 3_565 ?
C8 N2 C12 110.1(2) . . ?
C9 N2 C12 43.5(2) 3_565 . ?
C13 N2 C12 137.6(2) 3_565 . ?
C8 N2 C10 109.3(2) . . ?
C9 N2 C10 63.2(2) 3_565 . ?
C13 N2 C10 52.0(3) 3_565 . ?
C12 N2 C10 104.3(2) . . ?
C8 N2 C11 46.8(2) . 3_565 ?
C9 N2 C11 107.9(3) 3_565 3_565 ?
C13 N2 C11 105.6(3) 3_565 3_565 ?
C12 N2 C11 67.7(2) . 3_565 ?
C10 N2 C11 138.9(2) . 3_565 ?
C8 N2 Cu1 114.82(17) . . ?
C9 N2 Cu1 108.71(17) 3_565 . ?
C13 N2 Cu1 110.49(17) 3_565 . ?
C12 N2 Cu1 110.34(15) . . ?
C10 N2 Cu1 107.40(16) . . ?
C11 N2 Cu1 113.15(15) 3_565 . ?
N2 C8 C9 110.9(3) . . ?
N2 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N2 C8 H8AB 109.5 . . ?
C9 C8 H8AB 109.5 . . ?
H8A C8 H8AB 108.0 . . ?
N2 C9 C8 110.2(3) 3_565 . ?
N2 C9 C13 91.3(2) 3_565 3_565 ?
C8 C9 C13 47.5(2) . 3_565 ?
N2 C9 H9A 109.6 3_565 . ?
C8 C9 H9A 109.6 . . ?
C13 C9 H9A 154.7 3_565 . ?
N2 C9 H9AB 109.6 3_565 . ?
C8 C9 H9AB 109.6 . . ?
C13 C9 H9AB 76.5 3_565 . ?
H9A C9 H9AB 108.1 . . ?
N2 C10 C11 110.3(3) . . ?
N2 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
N2 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C10 108.6(3) 3_565 . ?
N2 C11 H11A 110.0 3_565 . ?
C10 C11 H11A 110.0 . . ?
N2 C11 H11B 110.0 3_565 . ?
C10 C11 H11B 110.0 . . ?
H11A C11 H11B 108.3 . . ?
N2 C12 C13 109.1(3) . . ?
N2 C12 H12A 109.9 . . ?
C13 C12 H12A 109.9 . . ?
N2 C12 H12B 109.9 . . ?
C13 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
N2 C12 H9AB 113.3(5) . 3_565 ?
C13 C12 H9AB 111.1(5) . 3_565 ?
H12A C12 H9AB 103.5 . 3_565 ?
H12B C12 H9AB 4.9 . 3_565 ?
N2 C13 C12 110.7(3) 3_565 . ?
N2 C13 C9 88.4(2) 3_565 3_565 ?
C12 C13 C9 33.2(2) . 3_565 ?
N2 C13 H13A 109.5 3_565 . ?
C12 C13 H13A 109.5 . . ?
C9 C13 H13A 95.9 3_565 . ?
N2 C13 H13B 109.5 3_565 . ?
C12 C13 H13B 109.5 . . ?
C9 C13 H13B 142.2 3_565 . ?
H13A C13 H13B 108.1 . . ?
H1OW O1W H2OW 104.4(19) . . ?

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 O1 C1 O2 177.65(18) . . . . ?
Cu1 O1 C1 C2 -3.8(2) . . . . ?
C6 N1 C2 C3 3.2(3) . . . . ?
Cu1 N1 C2 C3 -177.73(14) . . . . ?
C6 N1 C2 C1 -174.03(17) . . . . ?
Cu1 N1 C2 C1 5.1(2) . . . . ?
O2 C1 C2 N1 178.07(19) . . . . ?
O1 C1 C2 N1 -0.6(2) . . . . ?
O2 C1 C2 C3 1.1(3) . . . . ?
O1 C1 C2 C3 -177.56(19) . . . . ?
N1 C2 C3 C4 -2.1(3) . . . . ?
C1 C2 C3 C4 174.67(19) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 2.8(3) . . . . ?
C2 N1 C6 C5 -1.2(3) . . . . ?
Cu1 N1 C6 C5 179.71(15) . . . . ?
C2 N1 C6 C7 177.19(17) . . . . ?
Cu1 N1 C6 C7 -1.9(2) . . . . ?
C4 C5 C6 N1 -1.8(3) . . . . ?
C4 C5 C6 C7 -179.8(2) . . . . ?
Cu1 O3 C7 O4 -177.31(18) . . . . ?
Cu1 O3 C7 C6 2.2(2) . . . . ?
N1 C6 C7 O4 179.21(19) . . . . ?
C5 C6 C7 O4 -2.6(3) . . . . ?
N1 C6 C7 O3 -0.4(2) . . . . ?
C5 C6 C7 O3 177.9(2) . . . . ?
C9 N2 C8 C9 -23.0(6) 3_565 . . . ?
C13 N2 C8 C9 68.1(3) 3_565 . . . ?
C12 N2 C8 C9 -66.0(4) . . . . ?
C10 N2 C8 C9 48.0(4) . . . . ?
C11 N2 C8 C9 -92.0(4) 3_565 . . . ?
Cu1 N2 C8 C9 168.8(2) . . . . ?
N2 C8 C9 N2 16.9(5) . . . 3_565 ?
N2 C8 C9 C13 -55.3(3) . . . 3_565 ?
C8 N2 C10 C11 -64.9(4) . . . . ?
C9 N2 C10 C11 67.4(3) 3_565 . . . ?
C13 N2 C10 C11 -87.3(4) 3_565 . . . ?
C12 N2 C10 C11 52.9(4) . . . . ?
C11 N2 C10 C11 -19.4(6) 3_565 . . . ?
Cu1 N2 C10 C11 170.0(3) . . . . ?
N2 C10 C11 N2 13.3(4) . . . 3_565 ?
C8 N2 C12 C13 47.6(4) . . . . ?
C9 N2 C12 C13 -88.5(4) 3_565 . . . ?
C13 N2 C12 C13 -21.0(6) 3_565 . . . ?
C10 N2 C12 C13 -69.6(3) . . . . ?
C11 N2 C12 C13 67.9(3) 3_565 . . . ?
Cu1 N2 C12 C13 175.4(2) . . . . ?
N2 C12 C13 N2 15.0(4) . . . 3_565 ?
N2 C12 C13 C9 65.7(3) . . . 3_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H2O5 O1W 0.835(10) 1.870(10) 2.703(2) 175(3) . yes
O5 H1O5 O4 0.831(10) 2.005(11) 2.833(2) 174(3) 4_665 yes
O1W H1OW O2 0.841(10) 2.001(12) 2.818(2) 163(3) 2_645 yes
O1W H2OW O4 0.839(10) 2.000(10) 2.837(2) 175(3) 1_655 yes

_refine_diff_density_max         0.513
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.096

