# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_DUT-49-pyrene
_audit_block_doi                 10.5517/ccdc.csd.cc257frm
_database_code_depnum_ccdc_archive 'CCDC 2003150'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv.12619064 2020
loop_
_audit_author_name
_audit_author_address
'Volodymyr Bon'
;Technische Universitaet Dresden
Germany
;
_audit_update_record             
;
2020-05-10 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;

# SQUEEZE RESULTS (Version = 150216)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.002 -0.003 -0.002 81932 19030 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        DUT-147
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H20 Cu2 N2 O10'
_chemical_formula_weight         863.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 '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 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0180 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.1490 1.8970 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      cubic
_space_group_IT_number           225
_space_group_name_H-M_alt        'F m -3 m'
_space_group_name_Hall           '-F 4 2 3'

_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'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y, x, -z'
'-y, -x, -z'
'y, -x, z'
'-y, x, z'
'x, z, -y'
'-x, z, y'
'-x, -z, -y'
'x, -z, y'
'z, y, -x'
'z, -y, x'
'-z, y, x'
'-z, -y, -x'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'z, x+1/2, y+1/2'
'z, -x+1/2, -y+1/2'
'-z, -x+1/2, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z+1/2, x+1/2'
'-y, z+1/2, -x+1/2'
'y, -z+1/2, -x+1/2'
'-y, -z+1/2, x+1/2'
'y, x+1/2, -z+1/2'
'-y, -x+1/2, -z+1/2'
'y, -x+1/2, z+1/2'
'-y, x+1/2, z+1/2'
'x, z+1/2, -y+1/2'
'-x, z+1/2, y+1/2'
'-x, -z+1/2, -y+1/2'
'x, -z+1/2, y+1/2'
'z, y+1/2, -x+1/2'
'z, -y+1/2, x+1/2'
'-z, y+1/2, x+1/2'
'-z, -y+1/2, -x+1/2'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+1/2, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'z+1/2, x, y+1/2'
'z+1/2, -x, -y+1/2'
'-z+1/2, -x, y+1/2'
'-z+1/2, x, -y+1/2'
'y+1/2, z, x+1/2'
'-y+1/2, z, -x+1/2'
'y+1/2, -z, -x+1/2'
'-y+1/2, -z, x+1/2'
'y+1/2, x, -z+1/2'
'-y+1/2, -x, -z+1/2'
'y+1/2, -x, z+1/2'
'-y+1/2, x, z+1/2'
'x+1/2, z, -y+1/2'
'-x+1/2, z, y+1/2'
'-x+1/2, -z, -y+1/2'
'x+1/2, -z, y+1/2'
'z+1/2, y, -x+1/2'
'z+1/2, -y, x+1/2'
'-z+1/2, y, x+1/2'
'-z+1/2, -y, -x+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'z+1/2, x+1/2, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x+1/2, y'
'-z+1/2, x+1/2, -y'
'y+1/2, z+1/2, x'
'-y+1/2, z+1/2, -x'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z+1/2, x'
'y+1/2, x+1/2, -z'
'-y+1/2, -x+1/2, -z'
'y+1/2, -x+1/2, z'
'-y+1/2, x+1/2, z'
'x+1/2, z+1/2, -y'
'-x+1/2, z+1/2, y'
'-x+1/2, -z+1/2, -y'
'x+1/2, -z+1/2, y'
'z+1/2, y+1/2, -x'
'z+1/2, -y+1/2, x'
'-z+1/2, y+1/2, x'
'-z+1/2, -y+1/2, -x'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-z, -x, -y'
'-z, x, y'
'z, x, -y'
'z, -x, y'
'-y, -z, -x'
'y, -z, x'
'-y, z, x'
'y, z, -x'
'-y, -x, z'
'y, x, z'
'-y, x, -z'
'y, -x, -z'
'-x, -z, y'
'x, -z, -y'
'x, z, y'
'-x, z, -y'
'-z, -y, x'
'-z, y, -x'
'z, -y, -x'
'z, y, x'
'-x, -y+1/2, -z+1/2'
'x, y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
'-x, y+1/2, z+1/2'
'-z, -x+1/2, -y+1/2'
'-z, x+1/2, y+1/2'
'z, x+1/2, -y+1/2'
'z, -x+1/2, y+1/2'
'-y, -z+1/2, -x+1/2'
'y, -z+1/2, x+1/2'
'-y, z+1/2, x+1/2'
'y, z+1/2, -x+1/2'
'-y, -x+1/2, z+1/2'
'y, x+1/2, z+1/2'
'-y, x+1/2, -z+1/2'
'y, -x+1/2, -z+1/2'
'-x, -z+1/2, y+1/2'
'x, -z+1/2, -y+1/2'
'x, z+1/2, y+1/2'
'-x, z+1/2, -y+1/2'
'-z, -y+1/2, x+1/2'
'-z, y+1/2, -x+1/2'
'z, -y+1/2, -x+1/2'
'z, y+1/2, x+1/2'
'-x+1/2, -y, -z+1/2'
'x+1/2, y, -z+1/2'
'x+1/2, -y, z+1/2'
'-x+1/2, y, z+1/2'
'-z+1/2, -x, -y+1/2'
'-z+1/2, x, y+1/2'
'z+1/2, x, -y+1/2'
'z+1/2, -x, y+1/2'
'-y+1/2, -z, -x+1/2'
'y+1/2, -z, x+1/2'
'-y+1/2, z, x+1/2'
'y+1/2, z, -x+1/2'
'-y+1/2, -x, z+1/2'
'y+1/2, x, z+1/2'
'-y+1/2, x, -z+1/2'
'y+1/2, -x, -z+1/2'
'-x+1/2, -z, y+1/2'
'x+1/2, -z, -y+1/2'
'x+1/2, z, y+1/2'
'-x+1/2, z, -y+1/2'
'-z+1/2, -y, x+1/2'
'-z+1/2, y, -x+1/2'
'z+1/2, -y, -x+1/2'
'z+1/2, y, x+1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'-z+1/2, -x+1/2, -y'
'-z+1/2, x+1/2, y'
'z+1/2, x+1/2, -y'
'z+1/2, -x+1/2, y'
'-y+1/2, -z+1/2, -x'
'y+1/2, -z+1/2, x'
'-y+1/2, z+1/2, x'
'y+1/2, z+1/2, -x'
'-y+1/2, -x+1/2, z'
'y+1/2, x+1/2, z'
'-y+1/2, x+1/2, -z'
'y+1/2, -x+1/2, -z'
'-x+1/2, -z+1/2, y'
'x+1/2, -z+1/2, -y'
'x+1/2, z+1/2, y'
'-x+1/2, z+1/2, -y'
'-z+1/2, -y+1/2, x'
'-z+1/2, y+1/2, -x'
'z+1/2, -y+1/2, -x'
'z+1/2, y+1/2, x'

_cell_length_a                   46.450(5)
_cell_length_b                   46.450(5)
_cell_length_c                   46.450(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     100221(35)
_cell_formula_units_Z            24
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    263
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      15.7

_exptl_crystal_description       cubic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.343
_exptl_crystal_F_000             10464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.010
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.500
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.89499
_diffrn_source                   synchrotron
_diffrn_source_type              'BESSY MX BL14.3'
_diffrn_radiation_monochromator  'Si 111'
_diffrn_measurement_device_type  'MX-225 CCD'
_diffrn_measurement_method       'Δφ scans'
_diffrn_reflns_number            46235
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_av_R_equivalents  0.1713
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_k_min       -56
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         0.956
_diffrn_reflns_theta_max         33.070
_diffrn_reflns_theta_full        32.479
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4582
_reflns_number_gt                2786
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'marCCD 1994-2002'
_computing_cell_refinement       'XDSAPP 2.0'
_computing_data_reduction        'XDSAPP 2.0'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 3.1'
_computing_publication_material  WinGX
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1505P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4582
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.2344
_refine_ls_wR_factor_gt          0.1862
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_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 0.5000 0.5000 0.85027(2) 0.0448(3) Uani 1 8 d S T P . .
Cu2 Cu 0.5000 0.5000 0.79366(2) 0.0560(3) Uani 1 8 d S T P . .
O1 O 0.45809(6) 0.5000 0.84587(6) 0.0681(8) Uani 1 2 d S T P . .
O2 O 0.45830(6) 0.5000 0.79770(6) 0.0837(10) Uani 1 2 d S T P . .
O3 O 0.5000 0.5000 0.89675(12) 0.093(2) Uani 1 8 d S T P . .
O4 O 0.5000 0.5000 0.74665(13) 0.128(3) Uani 1 8 d S T P . .
N1 N 0.32511(8) 0.5000 0.82511(8) 0.145(4) Uani 1 4 d S T P A .
C1 C 0.44560(10) 0.5000 0.82165(10) 0.0707(12) Uani 1 2 d S T P . .
C2 C 0.41366(10) 0.5000 0.82190(10) 0.0882(16) Uani 1 2 d S T P . .
C3 C 0.39836(9) 0.5000 0.84720(9) 0.0787(14) Uani 1 2 d S T P . .
H3A H 0.4080 0.5000 0.8647 0.094 Uiso 1 2 calc R U P . .
C4 C 0.36871(10) 0.5000 0.84659(9) 0.0981(19) Uani 1 2 d S T P . .
C5 C 0.35410(12) 0.5000 0.82017(11) 0.136(3) Uani 1 2 d S T P . .
C6 C 0.36878(13) 0.5000 0.79414(11) 0.147(3) Uani 1 2 d S T P . .
H6A H 0.3591 0.5000 0.7766 0.177 Uiso 1 2 calc R U P . .
C7 C 0.39831(13) 0.5000 0.79565(11) 0.120(2) Uani 1 2 d S T P . .
H7A H 0.4087 0.5000 0.7785 0.144 Uiso 1 2 calc R U P . .
C8 C 0.30305(12) 0.5000 0.80305(12) 0.140(5) Uani 1 4 d S T P . .
C9 C 0.30367(17) 0.5220(2) 0.78272(18) 0.145(4) Uani 0.5 1 d . . P A -1
H9A H 0.3178 0.5361 0.7836 0.174 Uiso 0.5 1 calc R U P A -1
C10 C 0.28249(16) 0.5226(2) 0.76063(16) 0.129(4) Uani 0.5 1 d . . P A -1
C11 C 0.26108(10) 0.5000 0.76108(10) 0.134(4) Uani 1 4 d S T P . .
C12 C 0.2842(2) 0.5438(3) 0.7375(2) 0.195(6) Uani 0.5 1 d . . P . .
H12A H 0.2992 0.5571 0.7370 0.234 Uiso 0.5 1 calc R U P A .


_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 O1 1.957(3) 110 ?
Cu1 O1 1.957(3) 109_665 ?
Cu1 O1 1.957(3) 2_665 ?
Cu1 O1 1.957(3) . ?
Cu1 O3 2.159(6) . ?
Cu1 Cu2 2.6293(12) . ?
Cu2 O2 1.946(3) . ?
Cu2 O2 1.946(3) 109_665 ?
Cu2 O2 1.946(3) 2_665 ?
Cu2 O2 1.946(3) 110 ?
Cu2 O4 2.184(6) . ?
O1 C1 1.266(5) . ?
O2 C1 1.259(5) . ?
N1 C5 1.366(6) 70_465 ?
N1 C5 1.366(6) . ?
N1 C8 1.449(9) . ?
C1 C2 1.484(6) . ?
C2 C3 1.373(6) . ?
C2 C7 1.412(6) . ?
C3 C4 1.378(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.402(6) . ?
C4 C4 1.453(9) 70_465 ?
C5 C6 1.388(7) . ?
C6 C7 1.374(8) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.391(9) . ?
C9 C10 1.422(9) . ?
C9 H9A 0.9300 . ?
C10 C11 1.447(9) . ?
C10 C12 1.459(14) . ?
C11 C11 1.455(13) 145_566 ?
C12 C12 1.428(18) 118_656 ?
C12 H12A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 168.01(16) 110 109_665 ?
O1 Cu1 O1 89.375(17) 110 2_665 ?
O1 Cu1 O1 89.375(18) 109_665 2_665 ?
O1 Cu1 O1 89.375(18) 110 . ?
O1 Cu1 O1 89.375(17) 109_665 . ?
O1 Cu1 O1 168.01(16) 2_665 . ?
O1 Cu1 O3 95.99(8) 110 . ?
O1 Cu1 O3 95.99(8) 109_665 . ?
O1 Cu1 O3 95.99(8) 2_665 . ?
O1 Cu1 O3 95.99(8) . . ?
O1 Cu1 Cu2 84.01(8) 110 . ?
O1 Cu1 Cu2 84.01(8) 109_665 . ?
O1 Cu1 Cu2 84.01(8) 2_665 . ?
O1 Cu1 Cu2 84.01(8) . . ?
O3 Cu1 Cu2 180.0 . . ?
O2 Cu2 O2 89.468(17) . 109_665 ?
O2 Cu2 O2 168.94(17) . 2_665 ?
O2 Cu2 O2 89.468(18) 109_665 2_665 ?
O2 Cu2 O2 89.468(18) . 110 ?
O2 Cu2 O2 168.95(17) 109_665 110 ?
O2 Cu2 O2 89.468(17) 2_665 110 ?
O2 Cu2 O4 95.53(9) . . ?
O2 Cu2 O4 95.53(9) 109_665 . ?
O2 Cu2 O4 95.53(9) 2_665 . ?
O2 Cu2 O4 95.53(9) 110 . ?
O2 Cu2 Cu1 84.47(9) . . ?
O2 Cu2 Cu1 84.47(9) 109_665 . ?
O2 Cu2 Cu1 84.47(9) 2_665 . ?
O2 Cu2 Cu1 84.47(9) 110 . ?
O4 Cu2 Cu1 180.0 . . ?
C1 O1 Cu1 123.3(3) . . ?
C1 O2 Cu2 123.5(3) . . ?
C5 N1 C5 109.3(6) 70_465 . ?
C5 N1 C8 125.3(3) 70_465 . ?
C5 N1 C8 125.3(3) . . ?
O2 C1 O1 124.8(4) . . ?
O2 C1 C2 118.4(4) . . ?
O1 C1 C2 116.8(4) . . ?
C3 C2 C7 118.5(5) . . ?
C3 C2 C1 121.6(4) . . ?
C7 C2 C1 119.9(5) . . ?
C2 C3 C4 120.0(4) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 C4 133.8(2) . 70_465 ?
C5 C4 C4 106.1(3) . 70_465 ?
N1 C5 C6 129.1(4) . . ?
N1 C5 C4 109.3(5) . . ?
C6 C5 C4 121.6(5) . . ?
C7 C6 C5 116.5(5) . . ?
C7 C6 H6A 121.8 . . ?
C5 C6 H6A 121.8 . . ?
C6 C7 C2 123.2(5) . . ?
C6 C7 H7A 118.4 . . ?
C2 C7 H7A 118.4 . . ?
C9 C8 N1 117.7(4) . . ?
C8 C9 C10 119.4(9) . . ?
C8 C9 H9A 120.3 . . ?
C10 C9 H9A 120.3 . . ?
C9 C10 C11 116.7(9) . . ?
C9 C10 C12 120.5(9) . . ?
C11 C10 C12 122.6(7) . . ?
C10 C11 C11 118.4(4) . 145_566 ?
C12 C12 C10 118.8(5) 118_656 . ?
C12 C12 H12A 120.6 118_656 . ?
C10 C12 H12A 120.6 . . ?

_refine_diff_density_max         0.465
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.055



_exptl_crystal_recrystallization_method 'solvothermal synthesis'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_DUT-49c
_audit_block_doi                 10.5517/ccdc.csd.cc257fwr
_database_code_depnum_ccdc_archive 'CCDC 2003154'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv.12619064 2020
loop_
_audit_author_name
_audit_author_address
'Volodymyr Bon'
;Technische Universitaet Dresden
Germany
;
_audit_update_record             
;
2020-05-10 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;

# SQUEEZE RESULTS (Version =  30715)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.001 -0.004 -0.002 104902 21490 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        DUT-161
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H22 Cu2 N2 O10'
_chemical_formula_weight         841.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 '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 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0180 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.1490 1.8970 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      cubic
_space_group_IT_number           225
_space_group_name_H-M_alt        'F m -3 m'
_space_group_name_Hall           '-F 4 2 3'

_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'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y, x, -z'
'-y, -x, -z'
'y, -x, z'
'-y, x, z'
'x, z, -y'
'-x, z, y'
'-x, -z, -y'
'x, -z, y'
'z, y, -x'
'z, -y, x'
'-z, y, x'
'-z, -y, -x'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'z, x+1/2, y+1/2'
'z, -x+1/2, -y+1/2'
'-z, -x+1/2, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z+1/2, x+1/2'
'-y, z+1/2, -x+1/2'
'y, -z+1/2, -x+1/2'
'-y, -z+1/2, x+1/2'
'y, x+1/2, -z+1/2'
'-y, -x+1/2, -z+1/2'
'y, -x+1/2, z+1/2'
'-y, x+1/2, z+1/2'
'x, z+1/2, -y+1/2'
'-x, z+1/2, y+1/2'
'-x, -z+1/2, -y+1/2'
'x, -z+1/2, y+1/2'
'z, y+1/2, -x+1/2'
'z, -y+1/2, x+1/2'
'-z, y+1/2, x+1/2'
'-z, -y+1/2, -x+1/2'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+1/2, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'z+1/2, x, y+1/2'
'z+1/2, -x, -y+1/2'
'-z+1/2, -x, y+1/2'
'-z+1/2, x, -y+1/2'
'y+1/2, z, x+1/2'
'-y+1/2, z, -x+1/2'
'y+1/2, -z, -x+1/2'
'-y+1/2, -z, x+1/2'
'y+1/2, x, -z+1/2'
'-y+1/2, -x, -z+1/2'
'y+1/2, -x, z+1/2'
'-y+1/2, x, z+1/2'
'x+1/2, z, -y+1/2'
'-x+1/2, z, y+1/2'
'-x+1/2, -z, -y+1/2'
'x+1/2, -z, y+1/2'
'z+1/2, y, -x+1/2'
'z+1/2, -y, x+1/2'
'-z+1/2, y, x+1/2'
'-z+1/2, -y, -x+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'z+1/2, x+1/2, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x+1/2, y'
'-z+1/2, x+1/2, -y'
'y+1/2, z+1/2, x'
'-y+1/2, z+1/2, -x'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z+1/2, x'
'y+1/2, x+1/2, -z'
'-y+1/2, -x+1/2, -z'
'y+1/2, -x+1/2, z'
'-y+1/2, x+1/2, z'
'x+1/2, z+1/2, -y'
'-x+1/2, z+1/2, y'
'-x+1/2, -z+1/2, -y'
'x+1/2, -z+1/2, y'
'z+1/2, y+1/2, -x'
'z+1/2, -y+1/2, x'
'-z+1/2, y+1/2, x'
'-z+1/2, -y+1/2, -x'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-z, -x, -y'
'-z, x, y'
'z, x, -y'
'z, -x, y'
'-y, -z, -x'
'y, -z, x'
'-y, z, x'
'y, z, -x'
'-y, -x, z'
'y, x, z'
'-y, x, -z'
'y, -x, -z'
'-x, -z, y'
'x, -z, -y'
'x, z, y'
'-x, z, -y'
'-z, -y, x'
'-z, y, -x'
'z, -y, -x'
'z, y, x'
'-x, -y+1/2, -z+1/2'
'x, y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
'-x, y+1/2, z+1/2'
'-z, -x+1/2, -y+1/2'
'-z, x+1/2, y+1/2'
'z, x+1/2, -y+1/2'
'z, -x+1/2, y+1/2'
'-y, -z+1/2, -x+1/2'
'y, -z+1/2, x+1/2'
'-y, z+1/2, x+1/2'
'y, z+1/2, -x+1/2'
'-y, -x+1/2, z+1/2'
'y, x+1/2, z+1/2'
'-y, x+1/2, -z+1/2'
'y, -x+1/2, -z+1/2'
'-x, -z+1/2, y+1/2'
'x, -z+1/2, -y+1/2'
'x, z+1/2, y+1/2'
'-x, z+1/2, -y+1/2'
'-z, -y+1/2, x+1/2'
'-z, y+1/2, -x+1/2'
'z, -y+1/2, -x+1/2'
'z, y+1/2, x+1/2'
'-x+1/2, -y, -z+1/2'
'x+1/2, y, -z+1/2'
'x+1/2, -y, z+1/2'
'-x+1/2, y, z+1/2'
'-z+1/2, -x, -y+1/2'
'-z+1/2, x, y+1/2'
'z+1/2, x, -y+1/2'
'z+1/2, -x, y+1/2'
'-y+1/2, -z, -x+1/2'
'y+1/2, -z, x+1/2'
'-y+1/2, z, x+1/2'
'y+1/2, z, -x+1/2'
'-y+1/2, -x, z+1/2'
'y+1/2, x, z+1/2'
'-y+1/2, x, -z+1/2'
'y+1/2, -x, -z+1/2'
'-x+1/2, -z, y+1/2'
'x+1/2, -z, -y+1/2'
'x+1/2, z, y+1/2'
'-x+1/2, z, -y+1/2'
'-z+1/2, -y, x+1/2'
'-z+1/2, y, -x+1/2'
'z+1/2, -y, -x+1/2'
'z+1/2, y, x+1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'-z+1/2, -x+1/2, -y'
'-z+1/2, x+1/2, y'
'z+1/2, x+1/2, -y'
'z+1/2, -x+1/2, y'
'-y+1/2, -z+1/2, -x'
'y+1/2, -z+1/2, x'
'-y+1/2, z+1/2, x'
'y+1/2, z+1/2, -x'
'-y+1/2, -x+1/2, z'
'y+1/2, x+1/2, z'
'-y+1/2, x+1/2, -z'
'y+1/2, -x+1/2, -z'
'-x+1/2, -z+1/2, y'
'x+1/2, -z+1/2, -y'
'x+1/2, z+1/2, y'
'-x+1/2, z+1/2, -y'
'-z+1/2, -y+1/2, x'
'-z+1/2, y+1/2, -x'
'z+1/2, -y+1/2, -x'
'z+1/2, y+1/2, x'

_cell_length_a                   49.760(6)
_cell_length_b                   49.760(6)
_cell_length_c                   49.760(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     123209(43)
_cell_formula_units_Z            24
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    173
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      16.4

_exptl_crystal_description       cubic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.272
_exptl_crystal_F_000             10224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.406
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.89499
_diffrn_source                   synchrotron
_diffrn_source_type              'BESSY BL MX-14.3'
_diffrn_radiation_monochromator  'Si 111'
_diffrn_measurement_device_type  'MX-225 CCD'
_diffrn_measurement_method       'Δφ scans'
_diffrn_reflns_number            56402
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0994
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       56
_diffrn_reflns_limit_k_min       -56
_diffrn_reflns_limit_k_max       55
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         0.893
_diffrn_reflns_theta_max         30.832
_diffrn_reflns_theta_full        30.832
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4651
_reflns_number_gt                3135
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'marCCD 1994-2002'
_computing_cell_refinement       'XDSAPP 2.0'
_computing_data_reduction        'XDSAPP 2.0'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 3.1'
_computing_publication_material  WinGX
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1416P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4651
_refine_ls_number_parameters     106
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.2094
_refine_ls_wR_factor_gt          0.1714
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.021
_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 0.30737(2) 0.5000 0.5000 0.0936(4) Uani 1 8 d S T P . .
Cu2 Cu 0.36020(2) 0.5000 0.5000 0.0666(3) Uani 1 8 d S T P . .
O1 O 0.31149(5) 0.5000 0.46095(6) 0.1182(10) Uani 1 2 d S T P . .
O2 O 0.35607(4) 0.5000 0.46091(5) 0.0909(7) Uani 1 2 d S T P . .
O3 O 0.26356(10) 0.5000 0.5000 0.183(3) Uani 1 8 d S T P . .
O4 O 0.40368(7) 0.5000 0.5000 0.1078(16) Uani 1 8 d S T P . .
N1 N 0.33679(6) 0.5000 0.33679(6) 0.177(3) Uani 1 4 d S T P A .
C1 C 0.33376(7) 0.5000 0.44924(8) 0.0962(11) Uani 1 2 d S T P . .
C2 C 0.33384(7) 0.5000 0.41952(8) 0.1140(14) Uani 1 2 d S T P . .
C3 C 0.30870(8) 0.5000 0.40451(11) 0.161(2) Uani 1 2 d S T P . .
H3A H 0.2926 0.5000 0.4140 0.193 Uiso 1 2 calc R U P . .
C4 C 0.30775(10) 0.5000 0.37810(12) 0.197(3) Uani 1 2 d S T P . .
H4A H 0.2913 0.5000 0.3691 0.237 Uiso 1 2 calc R U P . .
C5 C 0.33177(10) 0.5000 0.36388(10) 0.156(2) Uani 1 2 d S T P . .
C6 C 0.35691(7) 0.5000 0.37774(8) 0.1230(16) Uani 1 2 d S T P . .
C7 C 0.35732(7) 0.5000 0.40522(7) 0.1037(13) Uani 1 2 d S T P . .
H7A H 0.3737 0.5000 0.4143 0.124 Uiso 1 2 calc R U P . .
C8 C 0.31610(9) 0.5000 0.31610(9) 0.200(5) Uani 1 4 d DS T P . .
C9 C 0.29852(16) 0.51937(19) 0.31528(16) 0.233(7) Uani 0.5 1 d D . P A -1
H9A H 0.2995 0.5329 0.3281 0.279 Uiso 0.5 1 calc R U P A -1
C10 C 0.27834(17) 0.5206(2) 0.29608(17) 0.272(8) Uani 0.5 1 d D . P A -1
H10A H 0.2660 0.5347 0.2957 0.327 Uiso 0.5 1 calc R U P A -1
C11 C 0.27743(11) 0.5000 0.27743(11) 0.278(8) Uani 1 4 d DS T P . .
C12 C 0.2516(6) 0.4916(6) 0.2600(6) 0.197(9) Uani 0.25 1 d D . P A .
H12A H 0.2405 0.4771 0.2637 0.236 Uiso 0.25 1 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 O1 1.954(3) . ?
Cu1 O1 1.954(3) 98_556 ?
Cu1 O1 1.954(3) 114_566 ?
Cu1 O1 1.954(3) 17_556 ?
Cu1 O3 2.180(5) . ?
Cu1 Cu2 2.6285(9) . ?
Cu2 O2 1.956(2) 17_556 ?
Cu2 O2 1.956(2) 98_556 ?
Cu2 O2 1.956(2) 114_566 ?
Cu2 O2 1.956(2) . ?
Cu2 O4 2.164(4) . ?
O1 C1 1.252(4) . ?
O2 C1 1.253(4) . ?
N1 C5 1.371(5) . ?
N1 C5 1.371(5) 22_565 ?
N1 C8 1.456(7) . ?
C1 C2 1.479(5) . ?
C2 C7 1.368(5) . ?
C2 C3 1.457(5) . ?
C3 C4 1.315(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.389(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.429(5) . ?
C6 C7 1.368(5) . ?
C6 C6 1.466(9) 22_565 ?
C7 H7A 0.9300 . ?
C8 C9 1.303(8) . ?
C9 C10 1.387(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.384(9) . ?
C10 H10A 0.9300 . ?
C11 C12 1.606(10) 120 ?
C11 C12 1.606(10) . ?
C11 C12 1.606(10) 99_565 ?
C11 C12 1.606(10) 22_565 ?
C12 C12 1.308(19) 145_565 ?
C12 H12A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 167.97(14) . 98_556 ?
O1 Cu1 O1 89.370(15) . 114_566 ?
O1 Cu1 O1 89.370(15) 98_556 114_566 ?
O1 Cu1 O1 89.370(14) . 17_556 ?
O1 Cu1 O1 89.370(14) 98_556 17_556 ?
O1 Cu1 O1 167.96(14) 114_566 17_556 ?
O1 Cu1 O3 96.02(7) . . ?
O1 Cu1 O3 96.02(7) 98_556 . ?
O1 Cu1 O3 96.02(7) 114_566 . ?
O1 Cu1 O3 96.02(7) 17_556 . ?
O1 Cu1 Cu2 83.98(7) . . ?
O1 Cu1 Cu2 83.98(7) 98_556 . ?
O1 Cu1 Cu2 83.98(7) 114_566 . ?
O1 Cu1 Cu2 83.98(7) 17_556 . ?
O3 Cu1 Cu2 180.0 . . ?
O2 Cu2 O2 89.370(13) 17_556 98_556 ?
O2 Cu2 O2 167.96(12) 17_556 114_566 ?
O2 Cu2 O2 89.370(13) 98_556 114_566 ?
O2 Cu2 O2 89.370(13) 17_556 . ?
O2 Cu2 O2 167.96(12) 98_556 . ?
O2 Cu2 O2 89.370(13) 114_566 . ?
O2 Cu2 O4 96.02(6) 17_556 . ?
O2 Cu2 O4 96.02(6) 98_556 . ?
O2 Cu2 O4 96.02(6) 114_566 . ?
O2 Cu2 O4 96.02(6) . . ?
O2 Cu2 Cu1 83.98(6) 17_556 . ?
O2 Cu2 Cu1 83.98(6) 98_556 . ?
O2 Cu2 Cu1 83.98(6) 114_566 . ?
O2 Cu2 Cu1 83.98(6) . . ?
O4 Cu2 Cu1 180.0 . . ?
C1 O1 Cu1 123.7(2) . . ?
C1 O2 Cu2 123.6(2) . . ?
C5 N1 C5 111.0(5) . 22_565 ?
C5 N1 C8 124.5(2) . . ?
C5 N1 C8 124.5(2) 22_565 . ?
O1 C1 O2 124.7(4) . . ?
O1 C1 C2 117.9(3) . . ?
O2 C1 C2 117.5(3) . . ?
C7 C2 C3 117.8(4) . . ?
C7 C2 C1 121.5(3) . . ?
C3 C2 C1 120.7(4) . . ?
C4 C3 C2 122.9(5) . . ?
C4 C3 H3A 118.5 . . ?
C2 C3 H3A 118.5 . . ?
C3 C4 C5 118.6(4) . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 H4A 120.7 . . ?
N1 C5 C4 131.1(4) . . ?
N1 C5 C6 108.4(5) . . ?
C4 C5 C6 120.5(4) . . ?
C7 C6 C5 119.7(4) . . ?
C7 C6 C6 134.1(2) . 22_565 ?
C5 C6 C6 106.1(3) . 22_565 ?
C6 C7 C2 120.5(3) . . ?
C6 C7 H7A 119.8 . . ?
C2 C7 H7A 119.8 . . ?
C9 C8 N1 119.8(4) . . ?
C8 C9 C10 122.8(9) . . ?
C8 C9 H9A 118.6 . . ?
C10 C9 H9A 118.6 . . ?
C11 C10 C9 116.9(9) . . ?
C11 C10 H10A 121.6 . . ?
C9 C10 H10A 121.6 . . ?
C10 C11 C12 138.3(7) . 120 ?
C10 C11 C12 125.4(17) . . ?
C12 C11 C12 21(3) 120 . ?
C10 C11 C12 101.3(6) . 99_565 ?
C12 C11 C12 37.1(9) 120 99_565 ?
C12 C11 C12 30(2) . 99_565 ?
C10 C11 C12 111.3(15) . 22_565 ?
C12 C11 C12 30(2) 120 22_565 ?
C12 C11 C12 37.1(9) . 22_565 ?
C12 C11 C12 21(3) 99_565 22_565 ?
C12 C12 C11 110.1(14) 145_565 . ?
C12 C12 H12A 125.0 145_565 . ?
C11 C12 H12A 125.0 . . ?

_refine_diff_density_max         0.347
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.041



_exptl_crystal_recrystallization_method 'solvothermal synthesis'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_DUT-159end
_audit_block_doi                 10.5517/ccdc.csd.cc257ftp
_database_code_depnum_ccdc_archive 'CCDC 2003152'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv.12619064 2020
loop_
_audit_author_name
_audit_author_address
'Volodymyr Bon'
;Technische Universitaet Dresden
Germany
;
_audit_update_record             
;
2020-05-10 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        DUT-159
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H20 Cu2 N2 O10'
_chemical_formula_weight         767.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 '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 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0180 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.1490 1.8970 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           166
_space_group_name_H-M_alt        'R -3 m :H'
_space_group_name_Hall           '-R 3 2"'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'

_cell_length_a                   23.110(3)
_cell_length_b                   23.110(3)
_cell_length_c                   49.600(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     22941(8)
_cell_formula_units_Z            9
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    274
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      23.76

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.500
_exptl_crystal_F_000             3492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.814
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.89499
_diffrn_source                   synchrotron
_diffrn_source_type              'BESSY BL MX-14.3'
_diffrn_radiation_monochromator  'Si 111'
_diffrn_measurement_device_type  'MX-225 CCD'
_diffrn_measurement_method       'Δφ scans'
_diffrn_reflns_number            48209
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         1.382
_diffrn_reflns_theta_max         33.930
_diffrn_reflns_theta_full        32.479
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5577
_reflns_number_gt                3836
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'marCCD 1994-2002'
_computing_cell_refinement       'XDSAPP 2.0'
_computing_data_reduction        'XDSAPP 2.0'
_computing_structure_solution    'SHELXT 2016/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Diamond 3.1'
_computing_publication_material  WinGX
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1715P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5577
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.2252
_refine_ls_wR_factor_gt          0.2003
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_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
CU1 Cu 0.27810(2) 0.13905(2) 0.65226(2) 0.0984(2) Uani 1 2 d S T P . .
O1 O 0.25039(8) 0.18448(9) 0.67781(4) 0.1180(6) Uani 1 1 d . . . . .
O2 O 0.34422(8) 0.23211(10) 0.70255(4) 0.1207(6) Uani 1 1 d . . . . .
O3 O 0.18589(15) 0.09294(8) 0.62997(8) 0.1672(13) Uani 1 2 d S T P . .
N1 N 0.17209(10) 0.34418(19) 0.75758(7) 0.1393(12) Uani 1 2 d S T P . .
C1 C 0.28588(12) 0.22155(13) 0.69723(5) 0.1121(7) Uani 1 1 d . . . . .
C7 C 0.19356(12) 0.24204(14) 0.70918(5) 0.1095(7) Uani 1 1 d . . . . .
H7 H 0.167743 0.212355 0.695686 0.131 Uiso 1 1 calc R U . . .
C6 C 0.16835(13) 0.27369(15) 0.72428(6) 0.1168(7) Uani 1 1 d . . . . .
C2 C 0.25771(12) 0.25431(13) 0.71401(5) 0.1132(7) Uani 1 1 d . . . . .
C5 C 0.20728(16) 0.31729(17) 0.74550(6) 0.1332(10) Uani 1 1 d . . . . .
C9 C 0.18095(14) 0.3619(3) 0.80710(11) 0.1357(15) Uani 1 2 d S T P . .
C3 C 0.29479(14) 0.29676(16) 0.73511(7) 0.1330(10) Uani 1 1 d . . . . .
H3 H 0.337155 0.303265 0.738660 0.160 Uiso 1 1 calc R U . . .
C4 C 0.27132(16) 0.32876(19) 0.75056(7) 0.1488(12) Uani 1 1 d . . . . .
H4 H 0.297339 0.357664 0.764219 0.179 Uiso 1 1 calc R U . . .
C8 C 0.19579(14) 0.3916(3) 0.77983(12) 0.165(2) Uani 1 2 d S T P . .
H8A H 0.176135 0.419944 0.778124 0.198 Uiso 0.5 1 calc R U P . .
H8B H 0.243809 0.419944 0.778124 0.198 Uiso 0.5 1 calc R U P . .
C11 C 0.1843(2) 0.3686(4) 0.85498(13) 0.226(3) Uani 1 2 d S T P . .
H11 H 0.198498 0.396997 0.869831 0.271 Uiso 1 2 calc R U P . .
C10 C 0.19931(17) 0.3986(3) 0.82885(17) 0.205(3) Uani 1 2 d S T P . .
H10 H 0.222469 0.444939 0.827309 0.246 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 O1 1.9466(18) 24 ?
CU1 O1 1.9467(18) . ?
CU1 O2 1.961(2) 25_556 ?
CU1 O2 1.961(2) 12_556 ?
CU1 O3 2.151(3) . ?
CU1 CU1 2.6325(8) 25_556 ?
O1 C1 1.278(3) . ?
O2 C1 1.272(3) . ?
O2 CU1 1.961(2) 25_556 ?
N1 C5 1.383(3) 23 ?
N1 C5 1.383(3) . ?
N1 C8 1.456(5) . ?
C1 C2 1.477(4) . ?
C7 C6 1.364(3) . ?
C7 C2 1.384(3) . ?
C7 H7 0.9300 . ?
C6 C5 1.423(4) . ?
C6 C6 1.456(5) 23 ?
C2 C3 1.397(4) . ?
C5 C4 1.390(4) . ?
C9 C11 1.298(9) 31_556 ?
C9 C10 1.305(8) . ?
C9 C8 1.477(8) . ?
C3 C4 1.353(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C11 C9 1.298(9) 31_556 ?
C11 C10 1.428(10) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 CU1 O1 89.46(12) 24 . ?
O1 CU1 O2 89.14(9) 24 25_556 ?
O1 CU1 O2 168.57(8) . 25_556 ?
O1 CU1 O2 168.57(8) 24 12_556 ?
O1 CU1 O2 89.13(9) . 12_556 ?
O2 CU1 O2 90.00(12) 25_556 12_556 ?
O1 CU1 O3 95.17(10) 24 . ?
O1 CU1 O3 95.17(10) . . ?
O2 CU1 O3 96.26(10) 25_556 . ?
O2 CU1 O3 96.26(10) 12_556 . ?
O1 CU1 CU1 83.45(5) 24 25_556 ?
O1 CU1 CU1 83.45(5) . 25_556 ?
O2 CU1 CU1 85.12(5) 25_556 25_556 ?
O2 CU1 CU1 85.12(5) 12_556 25_556 ?
O3 CU1 CU1 178.05(11) . 25_556 ?
C1 O1 CU1 125.35(16) . . ?
C1 O2 CU1 122.81(17) . 25_556 ?
C5 N1 C5 108.8(3) 23 . ?
C5 N1 C8 125.61(16) 23 . ?
C5 N1 C8 125.62(17) . . ?
O2 C1 O1 123.3(2) . . ?
O2 C1 C2 118.8(2) . . ?
O1 C1 C2 118.0(2) . . ?
C6 C7 C2 119.7(2) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 C6 134.02(15) . 23 ?
C5 C6 C6 106.15(17) . 23 ?
C7 C2 C3 119.5(2) . . ?
C7 C2 C1 119.9(2) . . ?
C3 C2 C1 120.6(2) . . ?
N1 C5 C4 130.2(3) . . ?
N1 C5 C6 109.5(3) . . ?
C4 C5 C6 120.3(3) . . ?
C11 C9 C10 114.2(7) 31_556 . ?
C11 C9 C8 123.8(5) 31_556 . ?
C10 C9 C8 122.0(7) . . ?
C4 C3 C2 122.4(3) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 118.2(3) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N1 C8 C9 115.6(5) . . ?
N1 C8 H8A 108.4 . . ?
C9 C8 H8A 108.4 . . ?
N1 C8 H8B 108.4 . . ?
C9 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
C9 C11 C10 124.9(5) 31_556 . ?
C9 C11 H11 117.5 31_556 . ?
C10 C11 H11 117.5 . . ?
C9 C10 C11 120.9(7) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.048



_exptl_crystal_recrystallization_method 'solvothermal synthesis'
_chemical_properties_physical    Moisture-sensitive
_refine_special_details          SQUEEZE
####################################################################### 
# 
# 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_DUT-49-methylene
_audit_block_doi                 10.5517/ccdc.csd.cc257fxs
_database_code_depnum_ccdc_archive 'CCDC 2003155'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv.12619064 2020
loop_
_audit_author_name
_audit_author_address
'Volodymyr Bon'
;Technische Universitaet Dresden
Germany
;
_audit_update_record             
;
2020-05-10 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;

# SQUEEZE RESULTS (Version = 150216)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.001 -0.003 -0.001 104857 18030 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        DUT-162
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H24 Cu2 N2 O10'
_chemical_formula_weight         843.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 '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 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0180 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.1490 1.8970 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      cubic
_space_group_IT_number           225
_space_group_name_H-M_alt        'F m -3 m'
_space_group_name_Hall           '-F 4 2 3'

_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'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y, x, -z'
'-y, -x, -z'
'y, -x, z'
'-y, x, z'
'x, z, -y'
'-x, z, y'
'-x, -z, -y'
'x, -z, y'
'z, y, -x'
'z, -y, x'
'-z, y, x'
'-z, -y, -x'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'z, x+1/2, y+1/2'
'z, -x+1/2, -y+1/2'
'-z, -x+1/2, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z+1/2, x+1/2'
'-y, z+1/2, -x+1/2'
'y, -z+1/2, -x+1/2'
'-y, -z+1/2, x+1/2'
'y, x+1/2, -z+1/2'
'-y, -x+1/2, -z+1/2'
'y, -x+1/2, z+1/2'
'-y, x+1/2, z+1/2'
'x, z+1/2, -y+1/2'
'-x, z+1/2, y+1/2'
'-x, -z+1/2, -y+1/2'
'x, -z+1/2, y+1/2'
'z, y+1/2, -x+1/2'
'z, -y+1/2, x+1/2'
'-z, y+1/2, x+1/2'
'-z, -y+1/2, -x+1/2'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+1/2, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'z+1/2, x, y+1/2'
'z+1/2, -x, -y+1/2'
'-z+1/2, -x, y+1/2'
'-z+1/2, x, -y+1/2'
'y+1/2, z, x+1/2'
'-y+1/2, z, -x+1/2'
'y+1/2, -z, -x+1/2'
'-y+1/2, -z, x+1/2'
'y+1/2, x, -z+1/2'
'-y+1/2, -x, -z+1/2'
'y+1/2, -x, z+1/2'
'-y+1/2, x, z+1/2'
'x+1/2, z, -y+1/2'
'-x+1/2, z, y+1/2'
'-x+1/2, -z, -y+1/2'
'x+1/2, -z, y+1/2'
'z+1/2, y, -x+1/2'
'z+1/2, -y, x+1/2'
'-z+1/2, y, x+1/2'
'-z+1/2, -y, -x+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'z+1/2, x+1/2, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x+1/2, y'
'-z+1/2, x+1/2, -y'
'y+1/2, z+1/2, x'
'-y+1/2, z+1/2, -x'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z+1/2, x'
'y+1/2, x+1/2, -z'
'-y+1/2, -x+1/2, -z'
'y+1/2, -x+1/2, z'
'-y+1/2, x+1/2, z'
'x+1/2, z+1/2, -y'
'-x+1/2, z+1/2, y'
'-x+1/2, -z+1/2, -y'
'x+1/2, -z+1/2, y'
'z+1/2, y+1/2, -x'
'z+1/2, -y+1/2, x'
'-z+1/2, y+1/2, x'
'-z+1/2, -y+1/2, -x'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-z, -x, -y'
'-z, x, y'
'z, x, -y'
'z, -x, y'
'-y, -z, -x'
'y, -z, x'
'-y, z, x'
'y, z, -x'
'-y, -x, z'
'y, x, z'
'-y, x, -z'
'y, -x, -z'
'-x, -z, y'
'x, -z, -y'
'x, z, y'
'-x, z, -y'
'-z, -y, x'
'-z, y, -x'
'z, -y, -x'
'z, y, x'
'-x, -y+1/2, -z+1/2'
'x, y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
'-x, y+1/2, z+1/2'
'-z, -x+1/2, -y+1/2'
'-z, x+1/2, y+1/2'
'z, x+1/2, -y+1/2'
'z, -x+1/2, y+1/2'
'-y, -z+1/2, -x+1/2'
'y, -z+1/2, x+1/2'
'-y, z+1/2, x+1/2'
'y, z+1/2, -x+1/2'
'-y, -x+1/2, z+1/2'
'y, x+1/2, z+1/2'
'-y, x+1/2, -z+1/2'
'y, -x+1/2, -z+1/2'
'-x, -z+1/2, y+1/2'
'x, -z+1/2, -y+1/2'
'x, z+1/2, y+1/2'
'-x, z+1/2, -y+1/2'
'-z, -y+1/2, x+1/2'
'-z, y+1/2, -x+1/2'
'z, -y+1/2, -x+1/2'
'z, y+1/2, x+1/2'
'-x+1/2, -y, -z+1/2'
'x+1/2, y, -z+1/2'
'x+1/2, -y, z+1/2'
'-x+1/2, y, z+1/2'
'-z+1/2, -x, -y+1/2'
'-z+1/2, x, y+1/2'
'z+1/2, x, -y+1/2'
'z+1/2, -x, y+1/2'
'-y+1/2, -z, -x+1/2'
'y+1/2, -z, x+1/2'
'-y+1/2, z, x+1/2'
'y+1/2, z, -x+1/2'
'-y+1/2, -x, z+1/2'
'y+1/2, x, z+1/2'
'-y+1/2, x, -z+1/2'
'y+1/2, -x, -z+1/2'
'-x+1/2, -z, y+1/2'
'x+1/2, -z, -y+1/2'
'x+1/2, z, y+1/2'
'-x+1/2, z, -y+1/2'
'-z+1/2, -y, x+1/2'
'-z+1/2, y, -x+1/2'
'z+1/2, -y, -x+1/2'
'z+1/2, y, x+1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'-z+1/2, -x+1/2, -y'
'-z+1/2, x+1/2, y'
'z+1/2, x+1/2, -y'
'z+1/2, -x+1/2, y'
'-y+1/2, -z+1/2, -x'
'y+1/2, -z+1/2, x'
'-y+1/2, z+1/2, x'
'y+1/2, z+1/2, -x'
'-y+1/2, -x+1/2, z'
'y+1/2, x+1/2, z'
'-y+1/2, x+1/2, -z'
'y+1/2, -x+1/2, -z'
'-x+1/2, -z+1/2, y'
'x+1/2, -z+1/2, -y'
'x+1/2, z+1/2, y'
'-x+1/2, z+1/2, -y'
'-z+1/2, -y+1/2, x'
'-z+1/2, y+1/2, -x'
'z+1/2, -y+1/2, -x'
'z+1/2, y+1/2, x'

_cell_length_a                   49.590(6)
_cell_length_b                   49.590(6)
_cell_length_c                   49.590(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     121950(42)
_cell_formula_units_Z            24
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    202
_cell_measurement_theta_min      3.6
_cell_measurement_theta_max      17.4

_exptl_crystal_description       cubic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.276
_exptl_crystal_F_000             10272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.015
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.411
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.89499
_diffrn_source                   synchrotron
_diffrn_source_type              'BESSY MX BL14.3'
_diffrn_radiation_monochromator  'Si 111'
_diffrn_measurement_device_type  'MX-225 CCD'
_diffrn_measurement_method       'Δφ scans'
_diffrn_reflns_number            58786
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_av_R_equivalents  0.1763
_diffrn_reflns_limit_h_min       -61
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -59
_diffrn_reflns_limit_k_max       61
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         0.896
_diffrn_reflns_theta_max         33.535
_diffrn_reflns_theta_full        32.479
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5731
_reflns_number_gt                2545
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'marCCD 1994-2002'
_computing_cell_refinement       'XDSAPP 2.0'
_computing_data_reduction        'XDSAPP 2.0'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 3.1'
_computing_publication_material  WinGX
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1560P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5731
_refine_ls_number_parameters     106
_refine_ls_number_restraints     47
_refine_ls_R_factor_all          0.1467
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.2603
_refine_ls_wR_factor_gt          0.1932
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_restrained_S_all      1.047
_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
Cu1 Cu 0.5000 0.0000 0.69308(2) 0.1505(6) Uani 1 8 d S T P . .
Cu2 Cu 0.5000 0.0000 0.64014(2) 0.0977(4) Uani 1 8 d S T P . .
O1 O 0.5000 0.03933(7) 0.68896(6) 0.1697(14) Uani 1 2 d S T P . .
O2 O 0.5000 0.03916(5) 0.64425(4) 0.1203(10) Uani 1 2 d S T P . .
O3 O 0.5000 0.0000 0.73712(11) 0.246(5) Uani 1 8 d S T P . .
O4 O 0.5000 0.0000 0.59682(8) 0.1223(18) Uani 1 8 d S T P . .
N1 N 0.5000 0.16353(8) 0.66353(8) 0.234(4) Uani 1 4 d S T P A .
C1 C 0.5000 0.05088(11) 0.66671(9) 0.1398(18) Uani 1 2 d S T P . .
C2 C 0.5000 0.08058(12) 0.66665(10) 0.154(2) Uani 1 2 d S T P . .
C3 C 0.5000 0.09523(10) 0.64306(9) 0.1442(19) Uani 1 2 d S T P . .
H3A H 0.5000 0.0862 0.6266 0.173 Uiso 1 2 calc R U P . .
C4 C 0.5000 0.12313(10) 0.64325(8) 0.157(2) Uani 1 2 d S T P . .
C5 C 0.5000 0.13597(14) 0.66919(14) 0.201(3) Uani 1 2 d S T P . .
C6 C 0.5000 0.12272(16) 0.69293(13) 0.244(4) Uani 1 2 d S T P . .
H6A H 0.5000 0.1318 0.7093 0.293 Uiso 1 2 calc R U P . .
C7 C 0.5000 0.09599(16) 0.69159(10) 0.215(3) Uani 1 2 d S T P . .
H7A H 0.5000 0.0864 0.7077 0.258 Uiso 1 2 calc R U P . .
C8 C 0.5000 0.18461(10) 0.68461(10) 0.265(7) Uani 1 4 d DS TU P . .
C9 C 0.52170(17) 0.1846(2) 0.7019(2) 0.329(9) Uani 0.5 1 d D U P A -1
H9A H 0.5355 0.1720 0.7002 0.394 Uiso 0.5 1 calc R U P A -1
C10 C 0.52219(18) 0.2038(2) 0.7219(2) 0.424(10) Uani 0.5 1 d D U P A -1
H10A H 0.5362 0.2045 0.7344 0.509 Uiso 0.5 1 calc R U P A -1
C12 C 0.5060(10) 0.2360(3) 0.7547(3) 0.401(13) Uani 0.25 1 d D U P A -1
H12A H 0.5242 0.2422 0.7563 0.482 Uiso 0.25 1 d R U P A -1
H12B H 0.4989 0.2278 0.7707 0.482 Uiso 0.25 1 d R U P A -1
C11 C 0.5000 0.22305(10) 0.72305(10) 0.418(10) Uani 1 4 d DS TU 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 O1 1.961(4) . ?
Cu1 O1 1.961(4) 181 ?
Cu1 O1 1.961(4) 2_655 ?
Cu1 O1 1.961(4) 182_545 ?
Cu1 O3 2.184(5) . ?
Cu1 Cu2 2.6253(11) . ?
Cu2 O2 1.952(3) 182_545 ?
Cu2 O2 1.952(3) 181 ?
Cu2 O2 1.952(3) 2_655 ?
Cu2 O2 1.953(3) . ?
Cu2 O4 2.148(4) . ?
O1 C1 1.243(5) . ?
O2 C1 1.256(4) . ?
N1 C5 1.395(7) 42_645 ?
N1 C5 1.395(7) . ?
N1 C8 1.478(9) . ?
C1 C2 1.473(7) . ?
C2 C3 1.377(6) . ?
C2 C7 1.454(6) . ?
C3 C4 1.383(6) . ?
C3 H3A 0.9300 . ?
C4 C4 1.411(10) 42_645 ?
C4 C5 1.435(6) . ?
C5 C6 1.348(9) . ?
C6 C7 1.327(9) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.377(7) . ?
C8 C9 1.377(7) 42_645 ?
C9 C10 1.377(8) . ?
C9 H9A 0.9300 . ?
C10 C11 1.457(8) . ?
C10 H10A 0.9300 . ?
C12 C12 1.439(19) 42_645 ?
C12 C11 1.720(9) . ?
C12 H12A 0.9599 . ?
C12 H12B 0.9601 . ?
C11 C10 1.457(8) 42_645 ?
C11 C12 1.720(9) 42_645 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 89.378(18) . 181 ?
O1 Cu1 O1 168.04(17) . 2_655 ?
O1 Cu1 O1 89.378(18) 181 2_655 ?
O1 Cu1 O1 89.378(18) . 182_545 ?
O1 Cu1 O1 168.04(17) 181 182_545 ?
O1 Cu1 O1 89.378(18) 2_655 182_545 ?
O1 Cu1 O3 95.98(8) . . ?
O1 Cu1 O3 95.98(8) 181 . ?
O1 Cu1 O3 95.98(8) 2_655 . ?
O1 Cu1 O3 95.98(8) 182_545 . ?
O1 Cu1 Cu2 84.02(8) . . ?
O1 Cu1 Cu2 84.02(8) 181 . ?
O1 Cu1 Cu2 84.02(8) 2_655 . ?
O1 Cu1 Cu2 84.02(8) 182_545 . ?
O3 Cu1 Cu2 180.0 . . ?
O2 Cu2 O2 168.01(13) 182_545 181 ?
O2 Cu2 O2 89.375(14) 182_545 2_655 ?
O2 Cu2 O2 89.375(15) 181 2_655 ?
O2 Cu2 O2 89.375(15) 182_545 . ?
O2 Cu2 O2 89.375(14) 181 . ?
O2 Cu2 O2 168.01(13) 2_655 . ?
O2 Cu2 O4 95.99(7) 182_545 . ?
O2 Cu2 O4 95.99(7) 181 . ?
O2 Cu2 O4 95.99(7) 2_655 . ?
O2 Cu2 O4 95.99(7) . . ?
O2 Cu2 Cu1 84.01(7) 182_545 . ?
O2 Cu2 Cu1 84.01(7) 181 . ?
O2 Cu2 Cu1 84.01(7) 2_655 . ?
O2 Cu2 Cu1 84.01(7) . . ?
O4 Cu2 Cu1 180.0 . . ?
C1 O1 Cu1 123.4(3) . . ?
C1 O2 Cu2 123.5(3) . . ?
C5 N1 C5 113.2(7) 42_645 . ?
C5 N1 C8 123.4(3) 42_645 . ?
C5 N1 C8 123.4(3) . . ?
O1 C1 O2 125.0(5) . . ?
O1 C1 C2 117.5(4) . . ?
O2 C1 C2 117.4(4) . . ?
C3 C2 C7 116.4(6) . . ?
C3 C2 C1 122.0(4) . . ?
C7 C2 C1 121.6(6) . . ?
C2 C3 C4 121.5(4) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 C4 134.6(3) . 42_645 ?
C3 C4 C5 116.7(5) . . ?
C4 C4 C5 108.7(4) 42_645 . ?
C6 C5 N1 130.8(5) . . ?
C6 C5 C4 124.5(6) . . ?
N1 C5 C4 104.7(7) . . ?
C7 C6 C5 116.3(6) . . ?
C7 C6 H6A 121.8 . . ?
C5 C6 H6A 121.8 . . ?
C6 C7 C2 124.6(7) . . ?
C6 C7 H7A 117.7 . . ?
C2 C7 H7A 117.7 . . ?
C9 C8 C9 127.7(8) . 42_645 ?
C9 C8 N1 116.1(4) . . ?
C9 C8 N1 116.1(4) 42_645 . ?
C8 C9 C10 117.6(6) . . ?
C8 C9 H9A 121.2 . . ?
C10 C9 H9A 121.2 . . ?
C9 C10 C11 117.9(6) . . ?
C9 C10 H10A 121.1 . . ?
C11 C10 H10A 121.1 . . ?
C12 C12 C11 65.3(3) 42_645 . ?
C12 C12 H12A 103.5 42_645 . ?
C11 C12 H12A 110.9 . . ?
C12 C12 H12B 131.1 42_645 . ?
C11 C12 H12B 122.4 . . ?
H12A C12 H12B 114.4 . . ?
C10 C11 C10 121.4(6) 42_645 . ?
C10 C11 C12 137.8(14) 42_645 . ?
C10 C11 C12 98.5(10) . . ?
C10 C11 C12 98.5(10) 42_645 42_645 ?
C10 C11 C12 137.8(14) . 42_645 ?
C12 C11 C12 49.5(6) . 42_645 ?

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.040



_exptl_crystal_recrystallization_method 'solvothermal synthesis'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_DUT-49-hydrophenantren
_audit_block_doi                 10.5517/ccdc.csd.cc257fsn
_database_code_depnum_ccdc_archive 'CCDC 2003151'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv.12619064 2020
loop_
_audit_author_name
_audit_author_address
'Volodymyr Bon'
;Technische Universitaet Dresden
Germany
;
_audit_update_record             
;
2020-05-10 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;

# SQUEEZE RESULTS (Version = 150216)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.002 -0.003 -0.002 81642 24524 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        DUT-148
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H22 Cu2 N2 O10'
_chemical_formula_weight         841.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 '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 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0180 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.1490 1.8970 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      cubic
_space_group_IT_number           225
_space_group_name_H-M_alt        'F m -3 m'
_space_group_name_Hall           '-F 4 2 3'

_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'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y, x, -z'
'-y, -x, -z'
'y, -x, z'
'-y, x, z'
'x, z, -y'
'-x, z, y'
'-x, -z, -y'
'x, -z, y'
'z, y, -x'
'z, -y, x'
'-z, y, x'
'-z, -y, -x'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'z, x+1/2, y+1/2'
'z, -x+1/2, -y+1/2'
'-z, -x+1/2, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z+1/2, x+1/2'
'-y, z+1/2, -x+1/2'
'y, -z+1/2, -x+1/2'
'-y, -z+1/2, x+1/2'
'y, x+1/2, -z+1/2'
'-y, -x+1/2, -z+1/2'
'y, -x+1/2, z+1/2'
'-y, x+1/2, z+1/2'
'x, z+1/2, -y+1/2'
'-x, z+1/2, y+1/2'
'-x, -z+1/2, -y+1/2'
'x, -z+1/2, y+1/2'
'z, y+1/2, -x+1/2'
'z, -y+1/2, x+1/2'
'-z, y+1/2, x+1/2'
'-z, -y+1/2, -x+1/2'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+1/2, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'z+1/2, x, y+1/2'
'z+1/2, -x, -y+1/2'
'-z+1/2, -x, y+1/2'
'-z+1/2, x, -y+1/2'
'y+1/2, z, x+1/2'
'-y+1/2, z, -x+1/2'
'y+1/2, -z, -x+1/2'
'-y+1/2, -z, x+1/2'
'y+1/2, x, -z+1/2'
'-y+1/2, -x, -z+1/2'
'y+1/2, -x, z+1/2'
'-y+1/2, x, z+1/2'
'x+1/2, z, -y+1/2'
'-x+1/2, z, y+1/2'
'-x+1/2, -z, -y+1/2'
'x+1/2, -z, y+1/2'
'z+1/2, y, -x+1/2'
'z+1/2, -y, x+1/2'
'-z+1/2, y, x+1/2'
'-z+1/2, -y, -x+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'z+1/2, x+1/2, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x+1/2, y'
'-z+1/2, x+1/2, -y'
'y+1/2, z+1/2, x'
'-y+1/2, z+1/2, -x'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z+1/2, x'
'y+1/2, x+1/2, -z'
'-y+1/2, -x+1/2, -z'
'y+1/2, -x+1/2, z'
'-y+1/2, x+1/2, z'
'x+1/2, z+1/2, -y'
'-x+1/2, z+1/2, y'
'-x+1/2, -z+1/2, -y'
'x+1/2, -z+1/2, y'
'z+1/2, y+1/2, -x'
'z+1/2, -y+1/2, x'
'-z+1/2, y+1/2, x'
'-z+1/2, -y+1/2, -x'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-z, -x, -y'
'-z, x, y'
'z, x, -y'
'z, -x, y'
'-y, -z, -x'
'y, -z, x'
'-y, z, x'
'y, z, -x'
'-y, -x, z'
'y, x, z'
'-y, x, -z'
'y, -x, -z'
'-x, -z, y'
'x, -z, -y'
'x, z, y'
'-x, z, -y'
'-z, -y, x'
'-z, y, -x'
'z, -y, -x'
'z, y, x'
'-x, -y+1/2, -z+1/2'
'x, y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
'-x, y+1/2, z+1/2'
'-z, -x+1/2, -y+1/2'
'-z, x+1/2, y+1/2'
'z, x+1/2, -y+1/2'
'z, -x+1/2, y+1/2'
'-y, -z+1/2, -x+1/2'
'y, -z+1/2, x+1/2'
'-y, z+1/2, x+1/2'
'y, z+1/2, -x+1/2'
'-y, -x+1/2, z+1/2'
'y, x+1/2, z+1/2'
'-y, x+1/2, -z+1/2'
'y, -x+1/2, -z+1/2'
'-x, -z+1/2, y+1/2'
'x, -z+1/2, -y+1/2'
'x, z+1/2, y+1/2'
'-x, z+1/2, -y+1/2'
'-z, -y+1/2, x+1/2'
'-z, y+1/2, -x+1/2'
'z, -y+1/2, -x+1/2'
'z, y+1/2, x+1/2'
'-x+1/2, -y, -z+1/2'
'x+1/2, y, -z+1/2'
'x+1/2, -y, z+1/2'
'-x+1/2, y, z+1/2'
'-z+1/2, -x, -y+1/2'
'-z+1/2, x, y+1/2'
'z+1/2, x, -y+1/2'
'z+1/2, -x, y+1/2'
'-y+1/2, -z, -x+1/2'
'y+1/2, -z, x+1/2'
'-y+1/2, z, x+1/2'
'y+1/2, z, -x+1/2'
'-y+1/2, -x, z+1/2'
'y+1/2, x, z+1/2'
'-y+1/2, x, -z+1/2'
'y+1/2, -x, -z+1/2'
'-x+1/2, -z, y+1/2'
'x+1/2, -z, -y+1/2'
'x+1/2, z, y+1/2'
'-x+1/2, z, -y+1/2'
'-z+1/2, -y, x+1/2'
'-z+1/2, y, -x+1/2'
'z+1/2, -y, -x+1/2'
'z+1/2, y, x+1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'-z+1/2, -x+1/2, -y'
'-z+1/2, x+1/2, y'
'z+1/2, x+1/2, -y'
'z+1/2, -x+1/2, y'
'-y+1/2, -z+1/2, -x'
'y+1/2, -z+1/2, x'
'-y+1/2, z+1/2, x'
'y+1/2, z+1/2, -x'
'-y+1/2, -x+1/2, z'
'y+1/2, x+1/2, z'
'-y+1/2, x+1/2, -z'
'y+1/2, -x+1/2, -z'
'-x+1/2, -z+1/2, y'
'x+1/2, -z+1/2, -y'
'x+1/2, z+1/2, y'
'-x+1/2, z+1/2, -y'
'-z+1/2, -y+1/2, x'
'-z+1/2, y+1/2, -x'
'z+1/2, -y+1/2, -x'
'z+1/2, y+1/2, x'

_cell_length_a                   46.540(5)
_cell_length_b                   46.540(5)
_cell_length_c                   46.540(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     100804(35)
_cell_formula_units_Z            24
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    362
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      24.6

_exptl_crystal_description       cubic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.333
_exptl_crystal_F_000             10224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.497
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.89499
_diffrn_source                   synchrotron
_diffrn_source_type              'BESSY MX BL14.3'
_diffrn_radiation_monochromator  'Si 111'
_diffrn_measurement_device_type  'MX-225 CCD'
_diffrn_measurement_method       'Δφ scans'
_diffrn_reflns_number            53443
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_av_R_equivalents  0.1049
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -58
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         0.954
_diffrn_reflns_theta_max         36.062
_diffrn_reflns_theta_full        32.479
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5638
_reflns_number_gt                3564
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'marCCD 1994-2002'
_computing_cell_refinement       'XDSAPP 2.0'
_computing_data_reduction        'XDSAPP 2.0'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 3.1'
_computing_publication_material  WinGX
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1682P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5638
_refine_ls_number_parameters     106
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.2490
_refine_ls_wR_factor_gt          0.2043
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.027
_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
Cu1 Cu 0.5000 0.5000 0.79404(2) 0.0528(3) Uani 1 8 d S T P . .
Cu2 Cu 0.5000 0.5000 0.85053(2) 0.0414(2) Uani 1 8 d S T P . .
O1 O 0.5000 0.45834(6) 0.79825(5) 0.0802(8) Uani 1 2 d S T P . .
O2 O 0.5000 0.45809(5) 0.84612(5) 0.0634(6) Uani 1 2 d S T P . .
O3 O 0.5000 0.5000 0.74717(11) 0.119(3) Uani 1 8 d S T P . .
O4 O 0.5000 0.5000 0.89699(10) 0.0888(17) Uani 1 8 d S T P . .
N1 N 0.5000 0.32526(6) 0.82526(6) 0.133(3) Uani 1 4 d S T P . .
C1 C 0.5000 0.44577(8) 0.82234(7) 0.0661(9) Uani 1 2 d S T P . .
C2 C 0.5000 0.41368(8) 0.82219(7) 0.0772(11) Uani 1 2 d S T P . .
C3 C 0.5000 0.39864(8) 0.84748(7) 0.0733(11) Uani 1 2 d S T P . .
H3A H 0.5000 0.4084 0.8649 0.088 Uiso 1 2 calc R U P . .
C4 C 0.5000 0.36892(8) 0.84706(7) 0.0877(14) Uani 1 2 d S T P . .
C5 C 0.5000 0.35456(9) 0.82022(9) 0.111(2) Uani 1 2 d S T P . .
C6 C 0.5000 0.36938(11) 0.79465(9) 0.132(3) Uani 1 2 d S T P . .
H6A H 0.5000 0.3597 0.7772 0.159 Uiso 1 2 calc R U P . .
C7 C 0.5000 0.39875(10) 0.79566(9) 0.1094(19) Uani 1 2 d S T P . .
H7A H 0.5000 0.4091 0.7786 0.131 Uiso 1 2 calc R U P . .
C8 C 0.5000 0.30326(8) 0.80326(8) 0.123(3) Uani 1 4 d S T P . .
C9 C 0.5212(2) 0.30327(16) 0.78391(16) 0.156(4) Uani 0.5 1 d . . P . 1
H9A H 0.5362 0.3175 0.7846 0.187 Uiso 0.5 1 d R U P . 1
C10 C 0.5218(2) 0.28173(15) 0.76220(15) 0.140(4) Uani 0.5 1 d D . P . 1
H10A H 0.5372 0.2806 0.7486 0.169 Uiso 0.25 1 d R U P . 2
C12 C 0.5335(8) 0.2928(4) 0.7305(4) 0.39(3) Uani 0.25 1 d D U P . 1
H12A H 0.5215 0.3086 0.7241 0.467 Uiso 0.25 1 calc R U P . 1
H12B H 0.5529 0.3001 0.7326 0.467 Uiso 0.25 1 calc R U P . 1
C11 C 0.5000 0.26164(8) 0.76164(8) 0.124(3) Uani 1 4 d S T 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 O1 1.949(3) . ?
Cu1 O1 1.949(3) 109_665 ?
Cu1 O1 1.949(3) 2_665 ?
Cu1 O1 1.949(3) 110 ?
Cu1 O3 2.181(5) . ?
Cu1 Cu2 2.6288(10) . ?
Cu2 O2 1.961(2) 110 ?
Cu2 O2 1.961(2) 109_665 ?
Cu2 O2 1.961(2) 2_665 ?
Cu2 O2 1.961(2) . ?
Cu2 O4 2.162(4) . ?
O1 C1 1.265(4) . ?
O2 C1 1.246(4) . ?
N1 C5 1.384(5) . ?
N1 C5 1.384(5) 42_645 ?
N1 C8 1.448(7) . ?
C1 C2 1.494(5) . ?
C2 C3 1.369(5) . ?
C2 C7 1.417(5) . ?
C3 C4 1.383(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.417(4) . ?
C4 C4 1.438(8) 42_645 ?
C5 C6 1.375(6) . ?
C6 C7 1.367(6) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.337(8) . ?
C8 C9 1.337(8) 42_645 ?
C8 C9 1.337(8) 100_655 ?
C8 C9 1.337(8) 139_545 ?
C9 C9 1.274(18) 139_545 ?
C9 C10 1.424(7) . ?
C9 C10 1.914(9) 139_545 ?
C9 C9 1.98(2) 100_655 ?
C9 H9A 0.9601 . ?
C10 C10 1.285(16) 139_545 ?
C10 C11 1.380(8) . ?
C10 C12 1.656(18) . ?
C10 C9 1.914(9) 139_545 ?
C10 C10 2.028(19) 100_655 ?
C12 C12 1.531(18) 114_566 ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 C10 1.379(8) 139_545 ?
C11 C10 1.379(8) 42_645 ?
C11 C10 1.379(8) 100_655 ?
C11 C11 1.532(11) 121_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 89.422(15) . 109_665 ?
O1 Cu1 O1 168.47(14) . 2_665 ?
O1 Cu1 O1 89.422(15) 109_665 2_665 ?
O1 Cu1 O1 89.422(15) . 110 ?
O1 Cu1 O1 168.47(14) 109_665 110 ?
O1 Cu1 O1 89.422(15) 2_665 110 ?
O1 Cu1 O3 95.76(7) . . ?
O1 Cu1 O3 95.76(7) 109_665 . ?
O1 Cu1 O3 95.76(7) 2_665 . ?
O1 Cu1 O3 95.76(7) 110 . ?
O1 Cu1 Cu2 84.24(7) . . ?
O1 Cu1 Cu2 84.24(7) 109_665 . ?
O1 Cu1 Cu2 84.24(7) 2_665 . ?
O1 Cu1 Cu2 84.24(7) 110 . ?
O3 Cu1 Cu2 180.0 . . ?
O2 Cu2 O2 167.99(13) 110 109_665 ?
O2 Cu2 O2 89.373(14) 110 2_665 ?
O2 Cu2 O2 89.373(14) 109_665 2_665 ?
O2 Cu2 O2 89.373(14) 110 . ?
O2 Cu2 O2 89.373(14) 109_665 . ?
O2 Cu2 O2 167.99(13) 2_665 . ?
O2 Cu2 O4 96.00(6) 110 . ?
O2 Cu2 O4 96.00(6) 109_665 . ?
O2 Cu2 O4 96.00(6) 2_665 . ?
O2 Cu2 O4 96.01(6) . . ?
O2 Cu2 Cu1 84.00(6) 110 . ?
O2 Cu2 Cu1 84.00(6) 109_665 . ?
O2 Cu2 Cu1 84.00(6) 2_665 . ?
O2 Cu2 Cu1 83.99(6) . . ?
O4 Cu2 Cu1 180.0 . . ?
C1 O1 Cu1 123.3(2) . . ?
C1 O2 Cu2 123.4(2) . . ?
C5 N1 C5 109.5(4) . 42_645 ?
C5 N1 C8 125.2(2) . . ?
C5 N1 C8 125.2(2) 42_645 . ?
O2 C1 O1 125.1(3) . . ?
O2 C1 C2 117.7(3) . . ?
O1 C1 C2 117.3(3) . . ?
C3 C2 C7 119.9(4) . . ?
C3 C2 C1 120.5(3) . . ?
C7 C2 C1 119.7(3) . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C5 118.9(4) . . ?
C3 C4 C4 134.2(2) . 42_645 ?
C5 C4 C4 106.9(3) . 42_645 ?
C6 C5 N1 129.9(4) . . ?
C6 C5 C4 121.8(4) . . ?
N1 C5 C4 108.4(4) . . ?
C7 C6 C5 118.1(4) . . ?
C7 C6 H6A 120.9 . . ?
C5 C6 H6A 120.9 . . ?
C6 C7 C2 121.3(4) . . ?
C6 C7 H7A 119.3 . . ?
C2 C7 H7A 119.3 . . ?
C9 C8 C9 123.2(7) . 42_645 ?
C9 C8 C9 95.3(8) . 100_655 ?
C9 C8 C9 56.9(8) 42_645 100_655 ?
C9 C8 C9 56.9(8) . 139_545 ?
C9 C8 C9 95.3(8) 42_645 139_545 ?
C9 C8 C9 123.1(7) 100_655 139_545 ?
C9 C8 N1 118.4(4) . . ?
C9 C8 N1 118.4(4) 42_645 . ?
C9 C8 N1 118.4(4) 100_655 . ?
C9 C8 N1 118.4(4) 139_545 . ?
C9 C9 C8 61.5(4) 139_545 . ?
C9 C9 C10 90.2(5) 139_545 . ?
C8 C9 C10 119.4(8) . . ?
C9 C9 C10 48.0(3) 139_545 139_545 ?
C8 C9 C10 92.6(6) . 139_545 ?
C10 C9 C10 42.2(6) . 139_545 ?
C9 C9 C9 90.002(2) 139_545 100_655 ?
C8 C9 C9 42.3(4) . 100_655 ?
C10 C9 C9 91.0(6) . 100_655 ?
C10 C9 C9 90.8(4) 139_545 100_655 ?
C9 C9 H9A 117.7 139_545 . ?
C8 C9 H9A 120.9 . . ?
C10 C9 H9A 119.7 . . ?
C10 C9 H9A 132.9 139_545 . ?
C9 C9 H9A 136.4 100_655 . ?
C10 C10 C11 62.2(4) 139_545 . ?
C10 C10 C9 89.8(5) 139_545 . ?
C11 C10 C9 118.5(7) . . ?
C10 C10 C12 148.3(12) 139_545 . ?
C11 C10 C12 115.8(11) . . ?
C9 C10 C12 114.8(7) . . ?
C10 C10 C9 48.1(3) 139_545 139_545 ?
C11 C10 C9 92.6(5) . 139_545 ?
C9 C10 C9 41.7(6) . 139_545 ?
C12 C10 C9 151.5(10) . 139_545 ?
C10 C10 C10 90.002(2) 139_545 100_655 ?
C11 C10 C10 42.7(4) . 100_655 ?
C9 C10 C10 89.0(6) . 100_655 ?
C12 C10 C10 109.1(16) . 100_655 ?
C9 C10 C10 89.2(4) 139_545 100_655 ?
C12 C12 C10 114.3(5) 114_566 . ?
C12 C12 H12A 108.7 114_566 . ?
C10 C12 H12A 108.7 . . ?
C12 C12 H12B 108.7 114_566 . ?
C10 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C10 C11 C10 94.6(8) 139_545 42_645 ?
C10 C11 C10 121.0(7) 139_545 100_655 ?
C10 C11 C10 55.5(7) 42_645 100_655 ?
C10 C11 C10 55.5(7) 139_545 . ?
C10 C11 C10 121.0(7) 42_645 . ?
C10 C11 C10 94.6(8) 100_655 . ?
C10 C11 C11 119.5(3) 139_545 121_656 ?
C10 C11 C11 119.5(3) 42_645 121_656 ?
C10 C11 C11 119.5(3) 100_655 121_656 ?
C10 C11 C11 119.5(3) . 121_656 ?

_refine_diff_density_max         1.102
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.075



_exptl_crystal_recrystallization_method 'hydrothermal synthesis'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_DUT-49-acetylene
_audit_block_doi                 10.5517/ccdc.csd.cc257fvq
_database_code_depnum_ccdc_archive 'CCDC 2003153'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv.12619064 2020
loop_
_audit_author_name
_audit_author_address
'Volodymyr Bon'
;Technische Universitaet Dresden
Germany
;
_audit_update_record             
;
2020-05-10 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        DUT-160
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H20 Cu2 N2 O10'
_chemical_formula_weight         839.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 '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 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0180 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.1490 1.8970 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      cubic
_space_group_IT_number           225
_space_group_name_H-M_alt        'F m -3 m'
_space_group_name_Hall           '-F 4 2 3'

_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'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y, x, -z'
'-y, -x, -z'
'y, -x, z'
'-y, x, z'
'x, z, -y'
'-x, z, y'
'-x, -z, -y'
'x, -z, y'
'z, y, -x'
'z, -y, x'
'-z, y, x'
'-z, -y, -x'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'z, x+1/2, y+1/2'
'z, -x+1/2, -y+1/2'
'-z, -x+1/2, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z+1/2, x+1/2'
'-y, z+1/2, -x+1/2'
'y, -z+1/2, -x+1/2'
'-y, -z+1/2, x+1/2'
'y, x+1/2, -z+1/2'
'-y, -x+1/2, -z+1/2'
'y, -x+1/2, z+1/2'
'-y, x+1/2, z+1/2'
'x, z+1/2, -y+1/2'
'-x, z+1/2, y+1/2'
'-x, -z+1/2, -y+1/2'
'x, -z+1/2, y+1/2'
'z, y+1/2, -x+1/2'
'z, -y+1/2, x+1/2'
'-z, y+1/2, x+1/2'
'-z, -y+1/2, -x+1/2'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+1/2, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'z+1/2, x, y+1/2'
'z+1/2, -x, -y+1/2'
'-z+1/2, -x, y+1/2'
'-z+1/2, x, -y+1/2'
'y+1/2, z, x+1/2'
'-y+1/2, z, -x+1/2'
'y+1/2, -z, -x+1/2'
'-y+1/2, -z, x+1/2'
'y+1/2, x, -z+1/2'
'-y+1/2, -x, -z+1/2'
'y+1/2, -x, z+1/2'
'-y+1/2, x, z+1/2'
'x+1/2, z, -y+1/2'
'-x+1/2, z, y+1/2'
'-x+1/2, -z, -y+1/2'
'x+1/2, -z, y+1/2'
'z+1/2, y, -x+1/2'
'z+1/2, -y, x+1/2'
'-z+1/2, y, x+1/2'
'-z+1/2, -y, -x+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'z+1/2, x+1/2, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x+1/2, y'
'-z+1/2, x+1/2, -y'
'y+1/2, z+1/2, x'
'-y+1/2, z+1/2, -x'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z+1/2, x'
'y+1/2, x+1/2, -z'
'-y+1/2, -x+1/2, -z'
'y+1/2, -x+1/2, z'
'-y+1/2, x+1/2, z'
'x+1/2, z+1/2, -y'
'-x+1/2, z+1/2, y'
'-x+1/2, -z+1/2, -y'
'x+1/2, -z+1/2, y'
'z+1/2, y+1/2, -x'
'z+1/2, -y+1/2, x'
'-z+1/2, y+1/2, x'
'-z+1/2, -y+1/2, -x'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-z, -x, -y'
'-z, x, y'
'z, x, -y'
'z, -x, y'
'-y, -z, -x'
'y, -z, x'
'-y, z, x'
'y, z, -x'
'-y, -x, z'
'y, x, z'
'-y, x, -z'
'y, -x, -z'
'-x, -z, y'
'x, -z, -y'
'x, z, y'
'-x, z, -y'
'-z, -y, x'
'-z, y, -x'
'z, -y, -x'
'z, y, x'
'-x, -y+1/2, -z+1/2'
'x, y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
'-x, y+1/2, z+1/2'
'-z, -x+1/2, -y+1/2'
'-z, x+1/2, y+1/2'
'z, x+1/2, -y+1/2'
'z, -x+1/2, y+1/2'
'-y, -z+1/2, -x+1/2'
'y, -z+1/2, x+1/2'
'-y, z+1/2, x+1/2'
'y, z+1/2, -x+1/2'
'-y, -x+1/2, z+1/2'
'y, x+1/2, z+1/2'
'-y, x+1/2, -z+1/2'
'y, -x+1/2, -z+1/2'
'-x, -z+1/2, y+1/2'
'x, -z+1/2, -y+1/2'
'x, z+1/2, y+1/2'
'-x, z+1/2, -y+1/2'
'-z, -y+1/2, x+1/2'
'-z, y+1/2, -x+1/2'
'z, -y+1/2, -x+1/2'
'z, y+1/2, x+1/2'
'-x+1/2, -y, -z+1/2'
'x+1/2, y, -z+1/2'
'x+1/2, -y, z+1/2'
'-x+1/2, y, z+1/2'
'-z+1/2, -x, -y+1/2'
'-z+1/2, x, y+1/2'
'z+1/2, x, -y+1/2'
'z+1/2, -x, y+1/2'
'-y+1/2, -z, -x+1/2'
'y+1/2, -z, x+1/2'
'-y+1/2, z, x+1/2'
'y+1/2, z, -x+1/2'
'-y+1/2, -x, z+1/2'
'y+1/2, x, z+1/2'
'-y+1/2, x, -z+1/2'
'y+1/2, -x, -z+1/2'
'-x+1/2, -z, y+1/2'
'x+1/2, -z, -y+1/2'
'x+1/2, z, y+1/2'
'-x+1/2, z, -y+1/2'
'-z+1/2, -y, x+1/2'
'-z+1/2, y, -x+1/2'
'z+1/2, -y, -x+1/2'
'z+1/2, y, x+1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'-z+1/2, -x+1/2, -y'
'-z+1/2, x+1/2, y'
'z+1/2, x+1/2, -y'
'z+1/2, -x+1/2, y'
'-y+1/2, -z+1/2, -x'
'y+1/2, -z+1/2, x'
'-y+1/2, z+1/2, x'
'y+1/2, z+1/2, -x'
'-y+1/2, -x+1/2, z'
'y+1/2, x+1/2, z'
'-y+1/2, x+1/2, -z'
'y+1/2, -x+1/2, -z'
'-x+1/2, -z+1/2, y'
'x+1/2, -z+1/2, -y'
'x+1/2, z+1/2, y'
'-x+1/2, z+1/2, -y'
'-z+1/2, -y+1/2, x'
'-z+1/2, y+1/2, -x'
'z+1/2, -y+1/2, -x'
'z+1/2, y+1/2, x'

_cell_length_a                   50.110(6)
_cell_length_b                   50.110(6)
_cell_length_c                   50.110(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     125827(44)
_cell_formula_units_Z            24
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    284
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      17.8

_exptl_crystal_description       cubic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.266
_exptl_crystal_F_000             10176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.398
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.89499
_diffrn_source                   synchrotron
_diffrn_source_type              'BESSY MX BL14.3'
_diffrn_radiation_monochromator  'Si 111'
_diffrn_measurement_device_type  'MX-225 CCD'
_diffrn_measurement_method       'Δφ scans'
_diffrn_reflns_number            140813
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         0.886
_diffrn_reflns_theta_max         28.112
_diffrn_reflns_theta_full        28.112
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3736
_reflns_number_gt                3080
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'marCCD 1994-2002'
_computing_cell_refinement       'XDSAPP 2.0'
_computing_data_reduction        'XDSAPP 2.0'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 3.1'
_computing_publication_material  WinGX
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1680P)²+35.9357P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3736
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.2254
_refine_ls_wR_factor_gt          0.1921
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 0.5000 0.5000 0.13857(2) 0.0638(4) Uani 1 8 d S T P . .
Cu2 Cu 0.5000 0.5000 0.19153(2) 0.0812(4) Uani 1 8 d S T P . .
N1 N 0.66224(6) 0.5000 0.16224(6) 0.170(3) Uani 1 4 d S T P A .
O1 O 0.53902(4) 0.5000 0.14290(4) 0.0848(7) Uani 1 2 d S T P . .
O2 O 0.53888(5) 0.5000 0.18729(5) 0.1059(9) Uani 1 2 d S T P . .
O3 O 0.5000 0.5000 0.09563(8) 0.1107(16) Uani 1 8 d S T P . .
O4 O 0.5000 0.5000 0.23474(10) 0.157(3) Uani 1 8 d S T P . .
C1 C 0.55034(7) 0.5000 0.16525(6) 0.0913(11) Uani 1 2 d S T P . .
C2 C 0.58002(7) 0.5000 0.16522(6) 0.1021(12) Uani 1 2 d S T P . .
C3 C 0.59420(7) 0.5000 0.14169(6) 0.0938(11) Uani 1 2 d S T P . .
H3A H 0.5852 0.5000 0.1255 0.113 Uiso 1 2 calc R U P . .
C4 C 0.62173(8) 0.5000 0.14211(6) 0.1112(14) Uani 1 2 d S T P . .
C5 C 0.63517(9) 0.5000 0.16701(8) 0.140(2) Uani 1 2 d S T P . .
C6 C 0.62143(10) 0.5000 0.19072(8) 0.165(3) Uani 1 2 d S T P . .
H6A H 0.6304 0.5000 0.2070 0.198 Uiso 1 2 calc R U P . .
C7 C 0.59391(9) 0.5000 0.18969(7) 0.140(2) Uani 1 2 d S T P . .
H7A H 0.5843 0.5000 0.2055 0.168 Uiso 1 2 calc R U P . .
C8 C 0.68268(9) 0.5000 0.18268(9) 0.186(5) Uani 1 4 d S T P . .
C9 C 0.70045(15) 0.4810(2) 0.18331(16) 0.210(6) Uani 0.5 1 d . . P A -1
H9A H 0.6999 0.4673 0.1708 0.252 Uiso 0.5 1 calc R U P A -1
C10 C 0.72067(15) 0.4814(2) 0.20319(15) 0.232(7) Uani 0.5 1 d . . P A -1
H10A H 0.7336 0.4681 0.2032 0.279 Uiso 0.5 1 calc R U P A -1
C11 C 0.72144(11) 0.5000 0.22144(11) 0.242(8) Uani 1 4 d S T P . .
C12 C 0.74176(9) 0.5000 0.24176(9) 0.265(6) Uani 1 4 d S T P A .


_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 O1 1.967(2) . ?
Cu1 O1 1.967(2) 110 ?
Cu1 O1 1.967(2) 109_665 ?
Cu1 O1 1.967(2) 2_665 ?
Cu1 O3 2.152(4) . ?
Cu1 Cu2 2.6538(10) . ?
Cu2 O2 1.960(3) . ?
Cu2 O2 1.960(3) 109_665 ?
Cu2 O2 1.960(3) 2_665 ?
Cu2 O2 1.960(3) 110 ?
Cu2 O4 2.165(5) . ?
N1 C5 1.377(5) . ?
N1 C5 1.378(5) 70_564 ?
N1 C8 1.449(8) . ?
O1 C1 1.255(4) . ?
O2 C1 1.245(4) . ?
C1 C2 1.487(5) . ?
C2 C3 1.377(5) . ?
C2 C7 1.410(5) . ?
C3 C4 1.380(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.418(5) . ?
C4 C4 1.444(8) 70_564 ?
C5 C6 1.373(6) . ?
C6 C7 1.380(7) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.304(8) . ?
C9 C10 1.421(8) . ?
C9 H9A 0.9300 . ?
C10 C11 1.306(9) . ?
C10 H10A 0.9300 . ?
C11 C12 1.440(11) . ?
C12 C12 1.168(13) 145_665 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 89.303(14) . 110 ?
O1 Cu1 O1 89.303(14) . 109_665 ?
O1 Cu1 O1 167.34(13) 110 109_665 ?
O1 Cu1 O1 167.34(13) . 2_665 ?
O1 Cu1 O1 89.304(14) 110 2_665 ?
O1 Cu1 O1 89.304(14) 109_665 2_665 ?
O1 Cu1 O3 96.33(6) . . ?
O1 Cu1 O3 96.33(6) 110 . ?
O1 Cu1 O3 96.33(6) 109_665 . ?
O1 Cu1 O3 96.33(6) 2_665 . ?
O1 Cu1 Cu2 83.67(6) . . ?
O1 Cu1 Cu2 83.67(6) 110 . ?
O1 Cu1 Cu2 83.67(6) 109_665 . ?
O1 Cu1 Cu2 83.67(6) 2_665 . ?
O3 Cu1 Cu2 180.0 . . ?
O2 Cu2 O2 89.328(15) . 109_665 ?
O2 Cu2 O2 167.56(14) . 2_665 ?
O2 Cu2 O2 89.328(15) 109_665 2_665 ?
O2 Cu2 O2 89.328(15) . 110 ?
O2 Cu2 O2 167.57(14) 109_665 110 ?
O2 Cu2 O2 89.328(15) 2_665 110 ?
O2 Cu2 O4 96.22(7) . . ?
O2 Cu2 O4 96.22(7) 109_665 . ?
O2 Cu2 O4 96.22(7) 2_665 . ?
O2 Cu2 O4 96.22(7) 110 . ?
O2 Cu2 Cu1 83.78(7) . . ?
O2 Cu2 Cu1 83.78(7) 109_665 . ?
O2 Cu2 Cu1 83.78(7) 2_665 . ?
O2 Cu2 Cu1 83.78(7) 110 . ?
O4 Cu2 Cu1 180.0 . . ?
C5 N1 C5 110.0(5) . 70_564 ?
C5 N1 C8 125.0(2) . . ?
C5 N1 C8 125.0(2) 70_564 . ?
C1 O1 Cu1 123.2(2) . . ?
C1 O2 Cu2 123.7(2) . . ?
O2 C1 O1 125.7(3) . . ?
O2 C1 C2 117.5(3) . . ?
O1 C1 C2 116.8(3) . . ?
C3 C2 C7 119.4(4) . . ?
C3 C2 C1 121.1(3) . . ?
C7 C2 C1 119.5(3) . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 C4 134.12(19) . 70_564 ?
C5 C4 C4 106.6(3) . 70_564 ?
C6 C5 N1 130.1(4) . . ?
C6 C5 C4 121.6(4) . . ?
N1 C5 C4 108.4(4) . . ?
C5 C6 C7 117.9(4) . . ?
C5 C6 H6A 121.0 . . ?
C7 C6 H6A 121.0 . . ?
C6 C7 C2 121.7(4) . . ?
C6 C7 H7A 119.1 . . ?
C2 C7 H7A 119.1 . . ?
C9 C8 N1 120.0(4) . . ?
C8 C9 C10 119.6(9) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
C11 C10 C9 121.5(10) . . ?
C11 C10 H10A 119.3 . . ?
C9 C10 H10A 119.3 . . ?
C10 C11 C12 121.1(5) . . ?
C12 C12 C11 180.0(9) 145_665 . ?

_refine_diff_density_max         0.522
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.051



_exptl_crystal_recrystallization_method 'solvothermal synthesis'
_chemical_properties_physical    Moisture-sensitive
