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

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

data_oe_sq
_database_code_depnum_ccdc_archive 'CCDC 1922322'
loop_
_audit_author_name
_audit_author_address
'Harald Krautscheid'
;Universitaet Leipzig
Germany
;
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Cu N4 O5'
_chemical_formula_weight         403.84


# start Validation Reply Form
_vrf_PLAT420_oe_sq               
;
PROBLEM: D-H Without Acceptor       O5       --H5A      .     Please Check
RESPONSE: O5 and H5a belong to a water molecule weakly coordinating to Cu1. 
Since the SQUEEZE routine has been applied, there are no coordinates of 
solvent molecule atoms that can act as hydrogen bond acceptors.
;
# end Validation Reply Form


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   14.251(2)
_cell_length_b                   13.399(2)
_cell_length_c                   14.6369(19)
_cell_angle_alpha                90
_cell_angle_beta                 93.001(11)
_cell_angle_gamma                90
_cell_volume                     2790.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    10286
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.96


_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.961
_exptl_crystal_F_000             820
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    0.804
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270.
;
_exptl_absorpt_correction_T_min  0.8814
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'STOE IPDS-I'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23693
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.468
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6084
_reflns_number_gt                3520
_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       'STOE IPDS software'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-AREA'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE,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)+(0.0342P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6084
_refine_ls_number_parameters     245
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_restrained_S_all      0.826
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36894(16) 0.4910(2) 0.14127(18) 0.0306(5) Uani 1 1 d . . . . .
C2 C 0.28957(15) 0.43643(16) 0.18439(16) 0.0244(5) Uani 1 1 d . . . . .
C3 C 0.26384(14) 0.34086(16) 0.15394(14) 0.0221(4) Uani 1 1 d . . . . .
H3 H 0.2973 0.3092 0.1085 0.026 Uiso 1 1 calc R U . . .
C4 C 0.18861(13) 0.29339(15) 0.19147(13) 0.0184(4) Uani 1 1 d . . . . .
C5 C 0.13789(14) 0.33888(16) 0.25828(14) 0.0209(4) Uani 1 1 d . . . . .
H5 H 0.0865 0.3061 0.2827 0.025 Uiso 1 1 calc R U . . .
C6 C 0.16424(15) 0.43362(16) 0.28865(15) 0.0231(4) Uani 1 1 d . . . . .
C7 C 0.24001(16) 0.48184(14) 0.25177(18) 0.0254(5) Uani 1 1 d . . . . .
H7 H 0.2577 0.5458 0.2728 0.030 Uiso 1 1 calc R U . . .
C8 C 0.11249(16) 0.48148(17) 0.36424(16) 0.0257(5) Uani 1 1 d . . . . .
C9 C 0.04111(19) 0.25232(19) 0.03968(18) 0.0387(6) Uani 1 1 d . . . . .
H9A H 0.0801 0.2807 -0.0061 0.058 Uiso 1 1 calc R U . . .
H9B H 0.0223 0.3045 0.0808 0.058 Uiso 1 1 calc R U . . .
H9C H -0.0143 0.2224 0.0098 0.058 Uiso 1 1 calc R U . . .
C10 C 0.09499(14) 0.17490(16) 0.09246(14) 0.0219(4) Uani 1 1 d . . . . .
C11 C 0.19270(15) 0.10383(16) 0.19207(15) 0.0224(4) Uani 1 1 d . . . . .
C12 C 0.26620(15) 0.08375(16) 0.26444(15) 0.0250(5) Uani 1 1 d . . . . .
C13 C 0.28948(17) 0.14986(19) 0.33531(16) 0.0313(5) Uani 1 1 d . . . . .
H13 H 0.2585 0.2116 0.3386 0.038 Uiso 1 1 calc R U . . .
C14 C 0.35870(17) 0.12380(19) 0.40092(17) 0.0328(5) Uani 1 1 d . . . . .
H14 H 0.3742 0.1693 0.4482 0.039 Uiso 1 1 calc R U . . .
C15 C 0.38190(18) -0.02684(19) 0.33172(18) 0.0394(6) Uani 1 1 d . . . . .
H15 H 0.4136 -0.0883 0.3302 0.047 Uiso 1 1 calc R U . . .
C16 C 0.31407(16) -0.0062(2) 0.26341(17) 0.0376(5) Uani 1 1 d . . . . .
H16 H 0.3005 -0.0528 0.2166 0.045 Uiso 1 1 calc R U . . .
Cu1 Cu 0.5000 0.0000 0.5000 0.03730(12) Uani 1 2 d S . P . .
Cu2 Cu 0.0000 0.0000 0.0000 0.01822(9) Uani 1 2 d S . P . .
N1 N 0.16132(11) 0.19498(13) 0.16090(11) 0.0191(4) Uani 1 1 d . . . . .
N2 N 0.08729(12) 0.07815(13) 0.08350(12) 0.0216(4) Uani 1 1 d . . . . .
N3 N 0.14822(13) 0.03214(13) 0.14577(13) 0.0245(4) Uani 1 1 d . . . . .
N4 N 0.40442(13) 0.03663(16) 0.39982(14) 0.0294(4) Uani 1 1 d . . . . .
O1 O 0.41394(12) 0.44178(14) 0.08610(11) 0.0334(4) Uani 1 1 d . . . . .
O2 O 0.38373(16) 0.57955(16) 0.1631(2) 0.0756(8) Uani 1 1 d . . . . .
O3 O 0.04806(11) 0.42921(12) 0.39662(10) 0.0268(3) Uani 1 1 d . . . . .
O4 O 0.13361(12) 0.56689(14) 0.39145(13) 0.0428(5) Uani 1 1 d . . . . .
O5 O 0.56905(19) 0.1805(2) 0.4977(2) 0.0750(7) Uani 1 1 d D . . . .
H5A H 0.607(2) 0.223(2) 0.521(2) 0.090 Uiso 1 1 d D U . . .
H5B H 0.575(3) 0.187(3) 0.4408(8) 0.090 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.244(3) . ?
C1 O1 1.246(3) . ?
C1 C2 1.512(3) . ?
C2 C7 1.384(3) . ?
C2 C3 1.398(3) . ?
C3 C4 1.385(3) . ?
C4 C5 1.387(3) . ?
C4 N1 1.439(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.391(3) . ?
C6 C8 1.505(3) . ?
C8 O4 1.243(3) . ?
C8 O3 1.266(3) . ?
C9 C10 1.483(3) . ?
C10 N2 1.307(3) . ?
C10 N1 1.368(3) . ?
C11 N3 1.319(3) . ?
C11 N1 1.370(3) . ?
C11 C12 1.475(3) . ?
C12 C16 1.385(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.385(3) . ?
C14 N4 1.338(3) . ?
C15 N4 1.336(3) . ?
C15 C16 1.382(3) . ?
Cu1 O1 1.9653(15) 4_566 ?
Cu1 O1 1.9653(15) 2_645 ?
Cu1 N4 2.0092(19) . ?
Cu1 N4 2.0093(19) 3_656 ?
Cu2 O3 1.9408(14) 4_565 ?
Cu2 O3 1.9408(14) 2_545 ?
Cu2 N2 1.9946(18) 3 ?
Cu2 N2 1.9946(18) . ?
N2 N3 1.372(3) . ?
O1 Cu1 1.9653(15) 2_655 ?
O3 Cu2 1.9408(14) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 125.8(2) . . ?
O2 C1 C2 118.3(2) . . ?
O1 C1 C2 115.9(2) . . ?
C7 C2 C3 119.65(19) . . ?
C7 C2 C1 120.4(2) . . ?
C3 C2 C1 119.9(2) . . ?
C4 C3 C2 119.32(19) . . ?
C3 C4 C5 121.38(19) . . ?
C3 C4 N1 119.98(17) . . ?
C5 C4 N1 118.64(17) . . ?
C4 C5 C6 118.99(19) . . ?
C5 C6 C7 120.14(19) . . ?
C5 C6 C8 119.31(19) . . ?
C7 C6 C8 120.5(2) . . ?
C2 C7 C6 120.51(19) . . ?
O4 C8 O3 123.9(2) . . ?
O4 C8 C6 120.5(2) . . ?
O3 C8 C6 115.61(19) . . ?
N2 C10 N1 108.65(19) . . ?
N2 C10 C9 127.1(2) . . ?
N1 C10 C9 124.3(2) . . ?
N3 C11 N1 109.78(18) . . ?
N3 C11 C12 122.72(19) . . ?
N1 C11 C12 127.49(19) . . ?
C16 C12 C13 117.6(2) . . ?
C16 C12 C11 118.8(2) . . ?
C13 C12 C11 123.5(2) . . ?
C14 C13 C12 119.3(2) . . ?
N4 C14 C13 122.8(2) . . ?
N4 C15 C16 123.0(2) . . ?
C15 C16 C12 119.5(2) . . ?
O1 Cu1 O1 180.00(7) 4_566 2_645 ?
O1 Cu1 N4 87.08(7) 4_566 . ?
O1 Cu1 N4 92.92(7) 2_645 . ?
O1 Cu1 N4 92.92(7) 4_566 3_656 ?
O1 Cu1 N4 87.08(7) 2_645 3_656 ?
N4 Cu1 N4 180.00(11) . 3_656 ?
O3 Cu2 O3 180.00(12) 4_565 2_545 ?
O3 Cu2 N2 90.75(7) 4_565 3 ?
O3 Cu2 N2 89.25(7) 2_545 3 ?
O3 Cu2 N2 89.25(7) 4_565 . ?
O3 Cu2 N2 90.75(7) 2_545 . ?
N2 Cu2 N2 180.0 3 . ?
C10 N1 C11 105.64(17) . . ?
C10 N1 C4 124.95(17) . . ?
C11 N1 C4 129.41(17) . . ?
C10 N2 N3 109.40(17) . . ?
C10 N2 Cu2 128.95(15) . . ?
N3 N2 Cu2 121.60(13) . . ?
C11 N3 N2 106.54(17) . . ?
C15 N4 C14 117.8(2) . . ?
C15 N4 Cu1 121.07(16) . . ?
C14 N4 Cu1 121.09(17) . . ?
C1 O1 Cu1 124.42(17) . 2_655 ?
C8 O3 Cu2 108.29(14) . 2 ?

_refine_diff_density_max         0.346
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.056




####################################################################### 
# 
# 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_phase-1e
_database_code_depnum_ccdc_archive 'CCDC 1922325'
loop_
_audit_author_name
_audit_author_address
'Harald Krautscheid'
;Universitaet Leipzig
Germany
;
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT602_phase-1e            
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info
RESPONSE: The structure belongs to an activated MOF in its open pore phase.
;
_vrf_PLAT049_phase-1e            
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.9165 Check
RESPONSE: The structure belongs to an activated MOF in its open pore phase.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 Cu N4 O4'
_chemical_formula_weight         385.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.5518(4)
_cell_length_b                   13.9161(4)
_cell_length_c                   14.8283(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.716(3)
_cell_angle_gamma                90
_cell_volume                     2796.22(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    30369
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      70.83


_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.916
_exptl_crystal_F_000             780
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.262
_shelx_estimated_absorpt_T_min   0.824
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270.
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Finally a spherical absorption correction was done within STOE LANA.
;
_exptl_absorpt_correction_T_min  0.8634
_exptl_absorpt_correction_T_max  0.9323
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'GeniX 3D HF Cu'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33399
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.357
_diffrn_reflns_theta_max         70.456
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5258
_reflns_number_gt                3932
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-AREA'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1188P)²+0.4690P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5258
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1772
_refine_ls_wR_factor_gt          0.1684
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3655(2) 0.4663(2) 0.11493(18) 0.0274(6) Uani 1 1 d . . . . .
C2 C 0.28675(19) 0.41690(19) 0.16875(17) 0.0248(6) Uani 1 1 d . . . . .
C3 C 0.26074(18) 0.32315(18) 0.14702(16) 0.0236(5) Uani 1 1 d . . . . .
H3 H 0.2943 0.2896 0.1008 0.028 Uiso 1 1 calc R U . . .
C4 C 0.18508(18) 0.27907(18) 0.19375(16) 0.0214(5) Uani 1 1 d . . . . .
C5 C 0.13681(19) 0.32489(18) 0.26284(16) 0.0237(5) Uani 1 1 d . . . . .
H5 H 0.0854 0.2934 0.2942 0.028 Uiso 1 1 calc R U . . .
C6 C 0.16459(19) 0.41811(19) 0.28585(17) 0.0251(6) Uani 1 1 d . . . . .
C7 C 0.23785(19) 0.4643(2) 0.23808(17) 0.0269(6) Uani 1 1 d . . . . .
H7 H 0.2549 0.5288 0.2526 0.032 Uiso 1 1 calc R U . . .
C8 C 0.11526(19) 0.4682(2) 0.36367(18) 0.0268(6) Uani 1 1 d . . . . .
C9 C 0.0250(2) 0.2367(2) 0.05573(19) 0.0355(7) Uani 1 1 d . . . . .
H9A H 0.0421 0.2401 -0.0082 0.053 Uiso 1 1 calc R U . . .
H9B H 0.0362 0.2995 0.0840 0.053 Uiso 1 1 calc R U . . .
H9C H -0.0447 0.2190 0.0613 0.053 Uiso 1 1 calc R U . . .
C10 C 0.08742(18) 0.16347(18) 0.10132(16) 0.0229(5) Uani 1 1 d . . . . .
C11 C 0.19302(19) 0.09478(18) 0.19244(16) 0.0231(5) Uani 1 1 d . . . . .
C12 C 0.2683(2) 0.0758(2) 0.26375(17) 0.0268(6) Uani 1 1 d . . . . .
C13 C 0.3208(3) 0.1434(3) 0.3084(3) 0.0660(13) Uani 1 1 d . . . . .
H13 H 0.3116 0.2094 0.2943 0.079 Uiso 1 1 calc R U . . .
C14 C 0.3881(3) 0.1166(3) 0.3748(3) 0.0688(14) Uani 1 1 d . . . . .
H14 H 0.4247 0.1657 0.4046 0.083 Uiso 1 1 calc R U . . .
C15 C 0.3561(4) -0.0368(3) 0.3534(3) 0.0781(16) Uani 1 1 d . . . . .
H15 H 0.3688 -0.1024 0.3672 0.094 Uiso 1 1 calc R U . . .
C16 C 0.2876(4) -0.0165(3) 0.2863(3) 0.0783(17) Uani 1 1 d . . . . .
H16 H 0.2541 -0.0674 0.2560 0.094 Uiso 1 1 calc R U . . .
Cu1 Cu 0.5000 0.0000 0.5000 0.0233(2) Uani 1 2 d S . P . .
Cu2 Cu 0.0000 0.0000 0.0000 0.01825(19) Uani 1 2 d S . P . .
N1 N 0.15600(15) 0.18300(15) 0.16719(13) 0.0214(5) Uani 1 1 d . . . . .
N2 N 0.08457(15) 0.07026(15) 0.08866(14) 0.0233(5) Uani 1 1 d . . . . .
N3 N 0.15018(17) 0.02668(17) 0.14628(15) 0.0261(5) Uani 1 1 d . . . . .
N4 N 0.40407(16) 0.02823(18) 0.39869(14) 0.0282(5) Uani 1 1 d . . . . .
O1 O 0.42631(13) 0.41127(13) 0.07532(12) 0.0270(4) Uani 1 1 d . . . . .
O2 O 0.36679(16) 0.55486(14) 0.10857(15) 0.0398(5) Uani 1 1 d . . . . .
O3 O 0.05033(13) 0.41856(13) 0.40438(11) 0.0253(4) Uani 1 1 d . . . . .
O4 O 0.13731(16) 0.55186(15) 0.38364(15) 0.0395(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.236(4) . ?
C1 O1 1.274(3) . ?
C1 C2 1.507(4) . ?
C2 C3 1.388(4) . ?
C2 C7 1.396(4) . ?
C3 C4 1.388(4) . ?
C4 C5 1.379(3) . ?
C4 N1 1.447(3) . ?
C5 C6 1.392(4) . ?
C6 C7 1.385(4) . ?
C6 C8 1.511(3) . ?
C8 O4 1.238(4) . ?
C8 O3 1.276(3) . ?
C9 C10 1.483(4) . ?
C10 N2 1.311(3) . ?
C10 N1 1.367(3) . ?
C11 N3 1.301(3) . ?
C11 N1 1.376(3) . ?
C11 C12 1.484(3) . ?
C12 C13 1.349(4) . ?
C12 C16 1.352(5) . ?
C13 C14 1.386(5) . ?
C14 N4 1.297(4) . ?
C15 N4 1.297(5) . ?
C15 C16 1.381(5) . ?
Cu1 O1 1.9487(17) 4_566 ?
Cu1 O1 1.9487(17) 2_645 ?
Cu1 N4 2.013(2) . ?
Cu1 N4 2.013(2) 3_656 ?
Cu2 O3 1.9452(17) 4_565 ?
Cu2 O3 1.9452(17) 2_545 ?
Cu2 N2 1.990(2) 3 ?
Cu2 N2 1.990(2) . ?
N2 N3 1.367(3) . ?
O1 Cu1 1.9487(17) 2_655 ?
O3 Cu2 1.9453(17) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 123.7(2) . . ?
O2 C1 C2 120.4(2) . . ?
O1 C1 C2 115.9(2) . . ?
C3 C2 C7 119.6(2) . . ?
C3 C2 C1 119.1(2) . . ?
C7 C2 C1 121.3(2) . . ?
C4 C3 C2 119.1(2) . . ?
C5 C4 C3 121.8(2) . . ?
C5 C4 N1 120.0(2) . . ?
C3 C4 N1 118.2(2) . . ?
C4 C5 C6 118.9(2) . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 C8 120.2(2) . . ?
C5 C6 C8 119.7(2) . . ?
C6 C7 C2 120.5(3) . . ?
O4 C8 O3 124.2(2) . . ?
O4 C8 C6 120.6(2) . . ?
O3 C8 C6 115.2(2) . . ?
N2 C10 N1 108.5(2) . . ?
N2 C10 C9 126.8(2) . . ?
N1 C10 C9 124.6(2) . . ?
N3 C11 N1 110.3(2) . . ?
N3 C11 C12 122.9(2) . . ?
N1 C11 C12 126.7(2) . . ?
C13 C12 C16 116.3(3) . . ?
C13 C12 C11 125.4(3) . . ?
C16 C12 C11 118.3(3) . . ?
C12 C13 C14 120.0(3) . . ?
N4 C14 C13 123.7(3) . . ?
N4 C15 C16 123.9(4) . . ?
C12 C16 C15 119.9(3) . . ?
O1 Cu1 O1 180.00(8) 4_566 2_645 ?
O1 Cu1 N4 88.47(8) 4_566 . ?
O1 Cu1 N4 91.53(8) 2_645 . ?
O1 Cu1 N4 91.53(8) 4_566 3_656 ?
O1 Cu1 N4 88.47(8) 2_645 3_656 ?
N4 Cu1 N4 180.00(14) . 3_656 ?
O3 Cu2 O3 180.00(14) 4_565 2_545 ?
O3 Cu2 N2 90.51(8) 4_565 3 ?
O3 Cu2 N2 89.49(8) 2_545 3 ?
O3 Cu2 N2 89.49(8) 4_565 . ?
O3 Cu2 N2 90.51(8) 2_545 . ?
N2 Cu2 N2 180.0 3 . ?
C10 N1 C11 105.0(2) . . ?
C10 N1 C4 124.0(2) . . ?
C11 N1 C4 130.8(2) . . ?
C10 N2 N3 109.4(2) . . ?
C10 N2 Cu2 126.61(17) . . ?
N3 N2 Cu2 124.03(17) . . ?
C11 N3 N2 106.7(2) . . ?
C14 N4 C15 116.1(3) . . ?
C14 N4 Cu1 119.5(2) . . ?
C15 N4 Cu1 124.4(2) . . ?
C1 O1 Cu1 102.84(17) . 2_655 ?
C8 O3 Cu2 106.25(16) . 2 ?

_refine_diff_density_max         0.999
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.102

####################################################################### 
# 
# 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_phase-1c
_database_code_depnum_ccdc_archive 'CCDC 1922324'
loop_
_audit_author_name
_audit_author_address
'Harald Krautscheid'
;Universitaet Leipzig
Germany
;
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT369_phase-1c            
;
PROBLEM: Long   C(sp2)-C(sp2) Bond  C1       - C2       .       1.59 Ang.
RESPONSE: The structure is refined in space group Pc, but it is close to 
centrosymmetry.
;
_vrf_PLAT420_phase-1c            
;
PROBLEM: D-H Without Acceptor       O9       --H9       .     Please Check
RESPONSE: O9 and H9 belong to a methanol molecule coordinating to Cu1. 
Since the SQUEEZE routine has been applied, there are no coordinates
available of solvent molecule atoms that can act as hydrogen bond acceptors.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H24 Cu2 N8 O9'
_chemical_formula_weight         803.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

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

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

_cell_length_a                   13.7136(4)
_cell_length_b                   13.2270(5)
_cell_length_c                   15.1795(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.415(3)
_cell_angle_gamma                90
_cell_volume                     2748.52(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13916
_cell_measurement_theta_min      4.64
_cell_measurement_theta_max      70.92


_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.971
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    1.313
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270.
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_correction_T_min  0.4347
_exptl_absorpt_correction_T_max  0.9481
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'GeniX 3D HF Cu'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24796
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.437
_diffrn_reflns_theta_max         69.981
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6716
_reflns_number_gt                5142
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.998

_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-AREA'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
'Refined as a 2-component inversion twin.,Twin,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)+(0.0668P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.41(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6716
_refine_ls_number_parameters     473
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3742(9) 0.7508(6) 0.1392(9) 0.046(3) Uani 1 1 d . . . . .
C2 C 0.2919(5) 0.6904(5) 0.1863(5) 0.0253(15) Uani 1 1 d . . . . .
C3 C 0.2647(5) 0.5970(4) 0.1578(4) 0.0229(14) Uani 1 1 d . . . . .
H3 H 0.2984 0.5665 0.1118 0.027 Uiso 1 1 calc R U . . .
C4 C 0.1900(5) 0.5453(4) 0.1933(4) 0.0167(13) Uani 1 1 d . . . . .
C5 C 0.1401(5) 0.5911(4) 0.2633(4) 0.0202(13) Uani 1 1 d . . . . .
H5 H 0.0875 0.5566 0.2881 0.024 Uiso 1 1 calc R U . . .
C6 C 0.1675(5) 0.6828(4) 0.2941(4) 0.0199(13) Uani 1 1 d . . . . .
C7 C 0.2432(6) 0.7341(5) 0.2576(5) 0.0200(15) Uani 1 1 d . . . . .
H7 H 0.2628 0.7985 0.2800 0.024 Uiso 1 1 calc R U . . .
C8 C 0.1175(6) 0.7284(6) 0.3668(6) 0.0248(18) Uani 1 1 d . . . . .
C9 C 0.0352(6) 0.5054(4) 0.0469(5) 0.0329(18) Uani 1 1 d . . . . .
H9A H -0.0280 0.4763 0.0271 0.049 Uiso 1 1 calc R U . . .
H9B H 0.0697 0.5273 -0.0045 0.049 Uiso 1 1 calc R U . . .
H9C H 0.0249 0.5635 0.0852 0.049 Uiso 1 1 calc R U . . .
C10 C 0.0942(5) 0.4285(4) 0.0963(5) 0.0220(14) Uani 1 1 d . . . . .
C11 C 0.1961(5) 0.3551(5) 0.1882(5) 0.0235(15) Uani 1 1 d . . . . .
C12 C 0.2688(5) 0.3312(5) 0.2635(5) 0.0203(14) Uani 1 1 d . . . . .
C13 C 0.2837(6) 0.3903(5) 0.3370(5) 0.0320(17) Uani 1 1 d . . . . .
H13 H 0.2475 0.4509 0.3428 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3519(5) 0.3612(5) 0.4031(5) 0.0279(16) Uani 1 1 d . . . . .
H14 H 0.3609 0.4022 0.4543 0.033 Uiso 1 1 calc R U . . .
C15 C 0.3906(5) 0.2219(6) 0.3266(5) 0.0283(15) Uani 1 1 d . . . . .
H15 H 0.4295 0.1632 0.3202 0.034 Uiso 1 1 calc R U . . .
C16 C 0.3199(7) 0.2470(5) 0.2620(6) 0.029(2) Uani 1 1 d . . . . .
H16 H 0.3075 0.2016 0.2142 0.035 Uiso 1 1 calc R U . . .
C17 C 0.6420(7) -0.2461(4) 0.8665(7) 0.023(2) Uani 1 1 d . . . . .
C18 C 0.7194(5) -0.1914(5) 0.8219(5) 0.0249(15) Uani 1 1 d . . . . .
C19 C 0.7440(5) -0.0910(4) 0.8490(5) 0.0220(14) Uani 1 1 d . . . . .
H19 H 0.7111 -0.0579 0.8941 0.026 Uiso 1 1 calc R U . . .
C20 C 0.8202(5) -0.0426(4) 0.8050(4) 0.0195(13) Uani 1 1 d . . . . .
C21 C 0.8676(5) -0.0876(4) 0.7405(5) 0.0230(14) Uani 1 1 d . . . . .
H21 H 0.9193 -0.0538 0.7138 0.028 Uiso 1 1 calc R U . . .
C22 C 0.8389(5) -0.1866(4) 0.7129(4) 0.0193(13) Uani 1 1 d . . . . .
C23 C 0.7664(6) -0.2378(5) 0.7560(5) 0.0212(17) Uani 1 1 d . . . . .
H23 H 0.7498 -0.3052 0.7395 0.025 Uiso 1 1 calc R U . . .
C24 C 0.8853(7) -0.2353(6) 0.6335(6) 0.0241(18) Uani 1 1 d . . . . .
C25 C 0.9682(5) 0.0004(5) 0.9556(5) 0.0288(16) Uani 1 1 d . . . . .
H25A H 1.0356 -0.0017 0.9375 0.043 Uiso 1 1 calc R U . . .
H25B H 0.9374 -0.0656 0.9450 0.043 Uiso 1 1 calc R U . . .
H25C H 0.9683 0.0169 1.0185 0.043 Uiso 1 1 calc R U . . .
C26 C 0.9122(5) 0.0796(4) 0.9032(4) 0.0182(13) Uani 1 1 d . . . . .
C27 C 0.8111(5) 0.1489(4) 0.8030(4) 0.0190(14) Uani 1 1 d . . . . .
C28 C 0.7368(6) 0.1670(4) 0.7342(5) 0.0244(15) Uani 1 1 d . . . . .
C29 C 0.7248(5) 0.1022(5) 0.6603(5) 0.0267(15) Uani 1 1 d . . . . .
H29 H 0.7641 0.0434 0.6563 0.032 Uiso 1 1 calc R U . . .
C30 C 0.6570(5) 0.1251(5) 0.5957(5) 0.0279(15) Uani 1 1 d . . . . .
H30 H 0.6474 0.0793 0.5478 0.034 Uiso 1 1 calc R U . . .
C31 C 0.6158(7) 0.2774(7) 0.6652(6) 0.042(2) Uani 1 1 d . . . . .
H31 H 0.5826 0.3405 0.6633 0.050 Uiso 1 1 calc R U . . .
C32 C 0.6778(7) 0.2559(6) 0.7391(7) 0.042(3) Uani 1 1 d . . . . .
H32 H 0.6808 0.2981 0.7899 0.050 Uiso 1 1 calc R U . . .
Cu1 Cu 0.49629(11) 0.23286(6) 0.49936(9) 0.0230(2) Uani 1 1 d . . . . .
Cu2 Cu -0.00007(12) 0.25328(6) 0.00021(11) 0.01575(16) Uani 1 1 d . . . . .
N1 N 0.1621(4) 0.4461(4) 0.1636(4) 0.0217(12) Uani 1 1 d . . . . .
N2 N 0.0897(4) 0.3301(4) 0.0825(4) 0.0223(12) Uani 1 1 d . . . . .
N3 N 0.1557(4) 0.2845(4) 0.1419(4) 0.0241(12) Uani 1 1 d . . . . .
N4 N 0.4043(4) 0.2796(5) 0.3975(4) 0.0247(12) Uani 1 1 d . . . . .
N5 N 0.8476(4) 0.0555(3) 0.8340(3) 0.0169(11) Uani 1 1 d . . . . .
N6 N 0.9148(4) 0.1758(3) 0.9156(4) 0.0198(12) Uani 1 1 d . . . . .
N7 N 0.8527(4) 0.2257(5) 0.8535(4) 0.0211(11) Uani 1 1 d . . . . .
N8 N 0.6000(4) 0.2129(5) 0.5955(4) 0.0279(13) Uani 1 1 d . . . . .
O1 O 0.4072(3) 0.7071(4) 0.0792(3) 0.0282(10) Uani 1 1 d . . . . .
O2 O 0.3958(5) 0.8358(4) 0.1763(4) 0.0515(16) Uani 1 1 d . . . . .
O3 O 0.0537(4) 0.6730(3) 0.4031(3) 0.0245(11) Uani 1 1 d . . . . .
O4 O 0.1386(4) 0.8175(3) 0.3952(4) 0.0314(12) Uani 1 1 d . . . . .
O5 O 0.5882(3) -0.1858(3) 0.9165(3) 0.0261(11) Uani 1 1 d . . . . .
O6 O 0.6317(4) -0.3374(4) 0.8652(4) 0.0509(16) Uani 1 1 d . . . . .
O7 O 0.9476(3) -0.1785(3) 0.5966(3) 0.0194(9) Uani 1 1 d . . . . .
O8 O 0.8656(4) -0.3227(4) 0.6132(4) 0.0326(13) Uani 1 1 d . . . . .
C33 C 0.3460(8) 0.0295(10) 0.4825(7) 0.096(5) Uani 1 1 d . . . . .
H33A H 0.3495 -0.0445 0.4827 0.144 Uiso 1 1 calc R U . . .
H33B H 0.3076 0.0522 0.5312 0.144 Uiso 1 1 calc R U . . .
H33C H 0.3147 0.0526 0.4264 0.144 Uiso 1 1 calc R U . . .
O9 O 0.4361(4) 0.0678(4) 0.4924(4) 0.0435(12) Uani 1 1 d . . . . .
H9 H 0.4771 0.0219 0.4850 0.065 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.192(13) . ?
C1 O2 1.283(10) . ?
C1 C2 1.586(13) . ?
C2 C3 1.354(9) . ?
C2 C7 1.427(12) . ?
C3 C4 1.369(9) . ?
C4 N1 1.431(7) . ?
C4 C5 1.432(9) . ?
C5 C6 1.346(9) . ?
C6 C7 1.383(10) . ?
C6 C8 1.464(11) . ?
C8 O4 1.282(8) . ?
C8 O3 1.290(10) . ?
C9 C10 1.476(9) . ?
C10 N2 1.319(8) . ?
C10 N1 1.361(9) . ?
C11 N3 1.275(8) . ?
C11 N1 1.337(8) . ?
C11 C12 1.504(9) . ?
C12 C16 1.317(9) . ?
C12 C13 1.368(10) . ?
C13 C14 1.384(10) . ?
C14 N4 1.302(9) . ?
C15 N4 1.324(10) . ?
C15 C16 1.379(11) . ?
C17 O6 1.217(7) . ?
C17 O5 1.350(10) . ?
C17 C18 1.481(11) . ?
C18 C23 1.368(11) . ?
C18 C19 1.425(9) . ?
C19 C20 1.425(9) . ?
C20 C21 1.346(9) . ?
C20 N5 1.414(7) . ?
C21 C22 1.423(8) . ?
C22 C23 1.397(10) . ?
C22 C24 1.537(11) . ?
C24 O8 1.222(8) . ?
C24 O7 1.291(10) . ?
C25 C26 1.499(8) . ?
C26 N6 1.286(7) . ?
C26 N5 1.370(8) . ?
C27 N7 1.376(8) . ?
C27 N5 1.404(7) . ?
C27 C28 1.435(9) . ?
C28 C29 1.413(9) . ?
C28 C32 1.432(10) . ?
C29 C30 1.344(10) . ?
C30 N8 1.400(9) . ?
C31 N8 1.366(11) . ?
C31 C32 1.396(13) . ?
Cu1 O5 1.935(5) 2_554 ?
Cu1 O1 1.942(5) 2_565 ?
Cu1 N8 1.994(6) . ?
Cu1 N4 2.032(6) . ?
Cu1 O9 2.334(5) . ?
Cu2 O7 1.939(4) 2_454 ?
Cu2 O3 1.948(5) 2_564 ?
Cu2 N6 1.971(6) 1_454 ?
Cu2 N2 1.981(6) . ?
N2 N3 1.378(7) . ?
N6 N7 1.397(7) . ?
N6 Cu2 1.971(6) 1_656 ?
O1 Cu1 1.942(5) 2_564 ?
O3 Cu2 1.948(5) 2_565 ?
O5 Cu1 1.935(5) 2 ?
O7 Cu2 1.939(4) 2_655 ?
C33 O9 1.336(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 132.2(11) . . ?
O1 C1 C2 114.4(7) . . ?
O2 C1 C2 113.3(10) . . ?
C3 C2 C7 118.6(6) . . ?
C3 C2 C1 120.4(7) . . ?
C7 C2 C1 121.0(6) . . ?
C2 C3 C4 121.9(6) . . ?
C3 C4 N1 121.8(6) . . ?
C3 C4 C5 118.8(5) . . ?
N1 C4 C5 119.3(5) . . ?
C6 C5 C4 120.2(6) . . ?
C5 C6 C7 120.2(7) . . ?
C5 C6 C8 120.0(6) . . ?
C7 C6 C8 119.8(6) . . ?
C6 C7 C2 120.1(7) . . ?
O4 C8 O3 121.6(8) . . ?
O4 C8 C6 121.7(8) . . ?
O3 C8 C6 116.6(7) . . ?
N2 C10 N1 108.1(6) . . ?
N2 C10 C9 125.5(6) . . ?
N1 C10 C9 126.4(5) . . ?
N3 C11 N1 111.8(6) . . ?
N3 C11 C12 120.8(6) . . ?
N1 C11 C12 127.3(6) . . ?
C16 C12 C13 116.3(7) . . ?
C16 C12 C11 119.6(7) . . ?
C13 C12 C11 124.1(6) . . ?
C12 C13 C14 119.6(6) . . ?
N4 C14 C13 122.3(7) . . ?
N4 C15 C16 119.9(7) . . ?
C12 C16 C15 123.0(8) . . ?
O6 C17 O5 122.0(8) . . ?
O6 C17 C18 124.2(8) . . ?
O5 C17 C18 113.6(5) . . ?
C23 C18 C19 121.0(6) . . ?
C23 C18 C17 119.9(6) . . ?
C19 C18 C17 119.1(6) . . ?
C18 C19 C20 116.9(6) . . ?
C21 C20 N5 120.1(6) . . ?
C21 C20 C19 122.7(6) . . ?
N5 C20 C19 117.1(6) . . ?
C20 C21 C22 119.0(6) . . ?
C23 C22 C21 120.0(6) . . ?
C23 C22 C24 120.2(6) . . ?
C21 C22 C24 119.8(6) . . ?
C18 C23 C22 120.3(6) . . ?
O8 C24 O7 125.6(9) . . ?
O8 C24 C22 120.0(8) . . ?
O7 C24 C22 114.3(6) . . ?
N6 C26 N5 110.7(5) . . ?
N6 C26 C25 127.2(6) . . ?
N5 C26 C25 122.1(5) . . ?
N7 C27 N5 109.5(6) . . ?
N7 C27 C28 122.4(6) . . ?
N5 C27 C28 127.9(5) . . ?
C29 C28 C32 120.0(7) . . ?
C29 C28 C27 121.4(6) . . ?
C32 C28 C27 118.5(7) . . ?
C30 C29 C28 119.0(6) . . ?
C29 C30 N8 123.4(6) . . ?
N8 C31 C32 123.8(8) . . ?
C31 C32 C28 116.4(8) . . ?
O5 Cu1 O1 174.6(2) 2_554 2_565 ?
O5 Cu1 N8 88.2(2) 2_554 . ?
O1 Cu1 N8 92.6(2) 2_565 . ?
O5 Cu1 N4 90.1(2) 2_554 . ?
O1 Cu1 N4 88.0(2) 2_565 . ?
N8 Cu1 N4 168.6(3) . . ?
O5 Cu1 O9 84.95(19) 2_554 . ?
O1 Cu1 O9 100.2(2) 2_565 . ?
N8 Cu1 O9 98.3(2) . . ?
N4 Cu1 O9 92.8(2) . . ?
O7 Cu2 O3 179.3(2) 2_454 2_564 ?
O7 Cu2 N6 89.7(2) 2_454 1_454 ?
O3 Cu2 N6 90.2(2) 2_564 1_454 ?
O7 Cu2 N2 91.7(2) 2_454 . ?
O3 Cu2 N2 88.4(2) 2_564 . ?
N6 Cu2 N2 177.8(3) 1_454 . ?
C11 N1 C10 105.5(5) . . ?
C11 N1 C4 130.9(6) . . ?
C10 N1 C4 123.4(5) . . ?
C10 N2 N3 107.8(5) . . ?
C10 N2 Cu2 128.9(5) . . ?
N3 N2 Cu2 123.2(4) . . ?
C11 N3 N2 106.7(5) . . ?
C14 N4 C15 118.6(6) . . ?
C14 N4 Cu1 121.5(5) . . ?
C15 N4 Cu1 119.7(5) . . ?
C26 N5 C27 104.7(5) . . ?
C26 N5 C20 126.8(5) . . ?
C27 N5 C20 128.3(5) . . ?
C26 N6 N7 111.0(5) . . ?
C26 N6 Cu2 128.3(4) . 1_656 ?
N7 N6 Cu2 120.5(4) . 1_656 ?
C27 N7 N6 104.1(5) . . ?
C31 N8 C30 117.0(6) . . ?
C31 N8 Cu1 123.9(5) . . ?
C30 N8 Cu1 119.0(5) . . ?
C1 O1 Cu1 124.1(6) . 2_564 ?
C8 O3 Cu2 109.6(5) . 2_565 ?
C17 O5 Cu1 125.1(4) . 2 ?
C24 O7 Cu2 108.4(4) . 2_655 ?
C33 O9 Cu1 133.0(7) . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.069



####################################################################### 
# 
# 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_phase-1b
_database_code_depnum_ccdc_archive 'CCDC 1922323'
loop_
_audit_author_name
_audit_author_address
'Harald Krautscheid'
;Universitaet Leipzig
Germany
;
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_phase-1b            
;
PROBLEM: D-H Without Acceptor       O5       --H5A      .     Please Check
RESPONSE: O5, H5a and H5b belong to a water molecule weakly coordinating to Cu1. 
Since the SQUEEZE routine has been applied, there are no coordinates
available for solvent molecule atoms that can act as hydrogen bond acceptors.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Cu N4 O5'
_chemical_formula_weight         403.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.8663(4)
_cell_length_b                   13.2350(4)
_cell_length_c                   15.0241(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.199(2)
_cell_angle_gamma                90
_cell_volume                     2752.93(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    6154
_cell_measurement_theta_min      4.43
_cell_measurement_theta_max      70.83


_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.974
_exptl_crystal_F_000             820
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    1.326
_shelx_estimated_absorpt_T_min   0.841
_shelx_estimated_absorpt_T_max   0.897
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270.
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Finally a spherical absorption correction was done within STOE LANA.
;
_exptl_absorpt_correction_T_min  0.1964
_exptl_absorpt_correction_T_max  0.7400
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'GeniX 3D HF Cu'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29057
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.455
_diffrn_reflns_theta_max         69.999
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5133
_reflns_number_gt                3605
_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-AREA'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1085P)²+1.2647P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5133
_refine_ls_number_parameters     245
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1966
_refine_ls_wR_factor_gt          0.1906
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3669(3) 0.4935(4) 0.1367(4) 0.0525(12) Uani 1 1 d . . . . .
C2 C 0.2875(3) 0.4384(3) 0.1834(3) 0.0359(9) Uani 1 1 d . . . . .
C3 C 0.2625(3) 0.3417(3) 0.1547(2) 0.0316(8) Uani 1 1 d . . . . .
H3 H 0.2958 0.3100 0.1096 0.038 Uiso 1 1 calc R U . . .
C4 C 0.1875(2) 0.2929(3) 0.1940(2) 0.0252(7) Uani 1 1 d . . . . .
C5 C 0.1377(2) 0.3373(3) 0.2608(2) 0.0280(7) Uani 1 1 d . . . . .
H5 H 0.0860 0.3033 0.2857 0.034 Uiso 1 1 calc R U . . .
C6 C 0.1653(3) 0.4338(3) 0.2911(2) 0.0309(8) Uani 1 1 d . . . . .
C7 C 0.2401(3) 0.4832(3) 0.2502(3) 0.0367(9) Uani 1 1 d . . . . .
H7 H 0.2582 0.5486 0.2690 0.044 Uiso 1 1 calc R U . . .
C8 C 0.1160(3) 0.4800(3) 0.3672(3) 0.0351(9) Uani 1 1 d . . . . .
C9 C 0.0375(3) 0.2532(3) 0.0450(3) 0.0461(11) Uani 1 1 d . . . . .
H9A H 0.0336 0.2360 -0.0178 0.069 Uiso 1 1 calc R U . . .
H9B H 0.0695 0.3180 0.0534 0.069 Uiso 1 1 calc R U . . .
H9C H -0.0271 0.2572 0.0665 0.069 Uiso 1 1 calc R U . . .
C10 C 0.0937(2) 0.1739(3) 0.0960(2) 0.0287(7) Uani 1 1 d . . . . .
C11 C 0.1928(3) 0.1013(3) 0.1920(2) 0.0303(8) Uani 1 1 d . . . . .
C12 C 0.2668(3) 0.0806(3) 0.2640(2) 0.0334(8) Uani 1 1 d . . . . .
C13 C 0.2834(3) 0.1436(4) 0.3368(3) 0.0478(11) Uani 1 1 d . . . . .
H13 H 0.2487 0.2043 0.3409 0.057 Uiso 1 1 calc R U . . .
C14 C 0.3508(3) 0.1171(4) 0.4029(3) 0.0499(12) Uani 1 1 d . . . . .
H14 H 0.3614 0.1608 0.4519 0.060 Uiso 1 1 calc R U . . .
C15 C 0.3857(3) -0.0303(4) 0.3301(3) 0.0517(12) Uani 1 1 d . . . . .
H15 H 0.4208 -0.0909 0.3281 0.062 Uiso 1 1 calc R U . . .
C16 C 0.3201(3) -0.0084(3) 0.2621(3) 0.0477(11) Uani 1 1 d . . . . .
H16 H 0.3108 -0.0533 0.2139 0.057 Uiso 1 1 calc R U . . .
Cu1 Cu 0.5000 0.0000 0.5000 0.0612(4) Uani 1 2 d S . P . .
Cu2 Cu 0.0000 0.0000 0.0000 0.0251(2) Uani 1 2 d S . P . .
N1 N 0.1593(2) 0.1932(2) 0.16382(18) 0.0267(6) Uani 1 1 d . . . . .
N2 N 0.0876(2) 0.0765(2) 0.08408(19) 0.0289(7) Uani 1 1 d . . . . .
N3 N 0.1508(2) 0.0293(2) 0.1444(2) 0.0330(7) Uani 1 1 d . . . . .
N4 N 0.4020(2) 0.0322(3) 0.4007(2) 0.0406(8) Uani 1 1 d . . . . .
O1 O 0.4107(2) 0.4440(3) 0.08271(18) 0.0510(9) Uani 1 1 d . . . . .
O2 O 0.3828(4) 0.5857(3) 0.1590(4) 0.123(2) Uani 1 1 d . . . . .
O3 O 0.05164(19) 0.42648(19) 0.40136(16) 0.0337(6) Uani 1 1 d . . . . .
O4 O 0.1373(2) 0.5659(2) 0.3949(2) 0.0556(9) Uani 1 1 d . . . . .
O5 O 0.5697(6) 0.1854(6) 0.4955(7) 0.158(3) Uani 1 1 d D . . . .
H5A H 0.615(6) 0.228(7) 0.504(7) 0.189 Uiso 1 1 d D U . . .
H5B H 0.542(7) 0.206(8) 0.447(5) 0.189 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.229(6) . ?
C1 O2 1.281(6) . ?
C1 C2 1.524(5) . ?
C2 C7 1.366(5) . ?
C2 C3 1.388(5) . ?
C3 C4 1.385(5) . ?
C4 C5 1.382(5) . ?
C4 N1 1.442(4) . ?
C5 C6 1.402(5) . ?
C6 C7 1.398(5) . ?
C6 C8 1.496(5) . ?
C8 O4 1.241(5) . ?
C8 O3 1.270(5) . ?
C9 C10 1.493(5) . ?
C10 N2 1.303(5) . ?
C10 N1 1.352(4) . ?
C11 N3 1.308(5) . ?
C11 N1 1.360(5) . ?
C11 C12 1.475(5) . ?
C12 C13 1.384(6) . ?
C12 C16 1.392(6) . ?
C13 C14 1.372(6) . ?
C14 N4 1.330(5) . ?
C15 N4 1.355(6) . ?
C15 C16 1.361(6) . ?
Cu1 O1 1.949(3) 4_566 ?
Cu1 O1 1.949(3) 2_645 ?
Cu1 N4 2.007(3) . ?
Cu1 N4 2.007(3) 3_656 ?
Cu2 O3 1.943(2) 4_565 ?
Cu2 O3 1.943(2) 2_545 ?
Cu2 N2 1.982(3) . ?
Cu2 N2 1.982(3) 3 ?
N2 N3 1.375(4) . ?
O1 Cu1 1.949(3) 2_655 ?
O3 Cu2 1.943(2) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 126.6(4) . . ?
O1 C1 C2 116.4(4) . . ?
O2 C1 C2 117.0(4) . . ?
C7 C2 C3 120.4(3) . . ?
C7 C2 C1 121.3(4) . . ?
C3 C2 C1 118.3(4) . . ?
C4 C3 C2 118.6(3) . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 N1 118.7(3) . . ?
C3 C4 N1 119.3(3) . . ?
C4 C5 C6 119.0(3) . . ?
C7 C6 C5 118.7(3) . . ?
C7 C6 C8 121.8(3) . . ?
C5 C6 C8 119.5(3) . . ?
C2 C7 C6 121.3(3) . . ?
O4 C8 O3 122.4(4) . . ?
O4 C8 C6 121.4(4) . . ?
O3 C8 C6 116.2(3) . . ?
N2 C10 N1 109.0(3) . . ?
N2 C10 C9 126.7(3) . . ?
N1 C10 C9 124.3(3) . . ?
N3 C11 N1 110.3(3) . . ?
N3 C11 C12 122.4(3) . . ?
N1 C11 C12 127.3(3) . . ?
C13 C12 C16 117.5(4) . . ?
C13 C12 C11 123.1(3) . . ?
C16 C12 C11 119.4(4) . . ?
C14 C13 C12 119.6(4) . . ?
N4 C14 C13 122.8(4) . . ?
N4 C15 C16 122.2(4) . . ?
C15 C16 C12 119.9(4) . . ?
O1 Cu1 O1 180.00(12) 4_566 2_645 ?
O1 Cu1 N4 87.99(12) 4_566 . ?
O1 Cu1 N4 92.01(12) 2_645 . ?
O1 Cu1 N4 92.01(12) 4_566 3_656 ?
O1 Cu1 N4 87.99(13) 2_645 3_656 ?
N4 Cu1 N4 180.0 . 3_656 ?
O3 Cu2 O3 180.0(2) 4_565 2_545 ?
O3 Cu2 N2 89.50(11) 4_565 . ?
O3 Cu2 N2 90.50(11) 2_545 . ?
O3 Cu2 N2 90.50(11) 4_565 3 ?
O3 Cu2 N2 89.50(11) 2_545 3 ?
N2 Cu2 N2 180.00(13) . 3 ?
C10 N1 C11 105.6(3) . . ?
C10 N1 C4 124.6(3) . . ?
C11 N1 C4 129.7(3) . . ?
C10 N2 N3 109.0(3) . . ?
C10 N2 Cu2 128.7(2) . . ?
N3 N2 Cu2 122.2(2) . . ?
C11 N3 N2 106.1(3) . . ?
C14 N4 C15 118.0(4) . . ?
C14 N4 Cu1 120.1(3) . . ?
C15 N4 Cu1 121.9(3) . . ?
C1 O1 Cu1 125.0(3) . 2_655 ?
C8 O3 Cu2 109.0(2) . 2 ?

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.076



####################################################################### 
# 
# 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_Phase_1d
_database_code_depnum_ccdc_archive 'CCDC 1949910'
loop_
_audit_author_name
_audit_author_address
'Harald Krautscheid'
;Universitaet Leipzig
Germany
;
_audit_update_record             
;
2019-09-04 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;

_vrf_PLAT602_Phase_1d            
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info  
RESPONSE: The structure belongs to a porous metal-organic framework.
;

_chemical_name_mineral           ?
_cell_length_a                   14.5493(3)
_cell_length_b                   11.93948(14)
_cell_length_c                   14.1517(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.6939(5)
_cell_angle_gamma                90
_cell_volume                     2453.20(7)
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P1211
_cell_formula_units_Z            2
_exptl_crystal_description       powder

_chemical_formula_sum            'C32 H20 Cu2 N8 O10'
_chemical_formula_weight         803.6


# EXPERIMENTAL DATA

_exptl_special_details           
;
Sample was handled under nitrogen atmosphere. 
Measurement was performed in a glass capillary.
;

_diffrn_ambient_temperature      293(2)
_diffrn_source                   'sealed tube'
_diffrn_source_target            Cu
_diffrn_radiation_wavelength     1.5406
_diffrn_measurement_device_type  'STOE STADI-P'
_diffrn_radiation_monochromator  'germanium (111) monochromator crystal'
_diffrn_detector_type            'MYTHEN 1K (DECTRIS)'
_cell_measurement_temperature    293(2)
_pd_meas_2theta_range_min        2.00000
_pd_meas_2theta_range_max        91.99000
_pd_meas_2theta_range_inc        0.010000


# REFINEMENT DATA

_pd_proc_ls_special_details      
;
Linker molecules were treated as rigid bodies using the Z-matrix notation.
Atomic positions of the copper ions and water molecules were not constrained/restrained during refinement.
;

_pd_calc_method                  'Rietveld Refinement'
_pd_proc_ls_background_function  
;   
Chebyshev polynomial function with 37 coefficients.
;

_pd_proc_ls_prof_R_factor        0.0286
_pd_proc_ls_prof_wR_factor       0.0379
_refine_ls_goodness_of_fit_all   5.08

_pd_proc_2theta_range_min        2.0000
_pd_proc_2theta_range_max        91.9900
_pd_proc_2theta_range_inc        0.010000


_computing_structure_solution    EXPO2014
_computing_structure_refinement  TOPAS


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z '
'-x, y+1/2, -z '
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C1 C 2 0.1993(2) -0.26823(11) 0.11331(12) 1 3.95
C2 C 2 0.2601(2) -0.18140(6) 0.07047(8) 1 3.95
C3 C 2 0.2583(2) -0.07028(7) 0.10187(11) 1 3.95
H3 H 2 0.2185(2) -0.04867(11) 0.14737(14) 1 3.95
C4 C 2 0.3167(2) 0.00708(3) 0.06441(7) 1 3.95
C5 C 2 0.3772(2) -0.02303(3) -0.002825(18) 1 3.95
H5 H 2 0.4166(3) 0.02973(6) -0.026600(4) 1 3.95
C6 C 2 0.3780(2) -0.13312(3) -0.034210(3) 1 3.95
C7 C 2 0.3194(2) -0.211692(10) 0.00268(3) 1 3.95
H7 H 2 0.3202(2) -0.285372(3) -0.018585(15) 1 3.95
C8 C 2 0.4402(3) -0.16517(9) -0.11089(6) 1 3.95
C9 C 2 0.4418(4) 0.09936(6) 0.22526(4) 1 3.95
H9A H 2 0.4250(2) 0.021636(9) 0.2236093(10) 1 3.95
H9B H 2 0.5008(2) 0.10840(4) 0.19927(4) 1 3.95
H9C H 2 0.4453(2) 0.125417(16) 0.289529(5) 1 3.95
C10 C 2 0.3716(2) 0.16516(3) 0.16845(6) 1 3.95
C11 C 2 0.2620(3) 0.20939(6) 0.06239(15) 1 3.95
C12 C 2 0.1889(3) 0.20660(8) -0.0141(2) 1 3.95
C13 C 2 0.1342(3) 0.29784(11) -0.0399(3) 1 3.95
H13 H 2 0.1433(3) 0.36631(11) -0.0094(3) 1 3.95
C14 C 2 0.0653(4) 0.28594(13) -0.1122(3) 1 3.95
H14 H 2 0.0292(4) 0.34790(15) -0.1291(3) 1 3.95
C15 C 2 0.1019(3) 0.10210(10) -0.1332(2) 1 3.95
H15 H 2 0.0912(3) 0.03472(10) -0.1650(2) 1 3.95
C16 C 2 0.1716(3) 0.10654(8) -0.0623(2) 1 3.95
H16 H 2 0.2068(3) 0.04319(6) -0.04685(16) 1 3.95
Cu1 Cu 2 0.0636(4) -0.2969(7) 0.2529(4) 1 3.95
Cu2 Cu 2 0.4351(4) 0.3783(7) 0.2456(5) 1 3.95
N1 N 2 0.3156(2) 0.12189(4) 0.09631(10) 1 3.95
N2 N 2 0.3532(2) 0.27149(4) 0.17723(10) 1 3.95
N3 N 2 0.2842(3) 0.30118(6) 0.11116(15) 1 3.95
N4 N 2 0.0490(4) 0.19005(13) -0.1583(3) 1 3.95
O1 O 2 0.1373(2) -0.23512(16) 0.16297(17) 1 3.95
O2 O 2 0.2160(2) -0.36769(10) 0.09417(8) 1 3.95
O3 O 2 0.4828(3) -0.09222(13) -0.15277(8) 1 3.95
O4 O 2 0.4453(2) -0.26905(10) -0.12817(8) 1 3.95
C17 C 2 0.0677(3) 0.24738(14) 0.63153(14) 1 3.95
C18 C 2 0.1548(3) 0.22567(5) 0.58135(10) 1 3.95
C19 C 2 0.2096(3) 0.13252(4) 0.60616(12) 1 3.95
H19 H 2 0.1917(3) 0.08216(9) 0.65159(17) 1 3.95
C20 C 2 0.2905(3) 0.11623(4) 0.56203(9) 1 3.95
C21 C 2 0.3191(3) 0.19032(11) 0.49460(2) 1 3.95
H21 H 2 0.3742(3) 0.17883(17) 0.46630164(11) 1 3.95
C22 C 2 0.2641(3) 0.28216(11) 0.4698157(14) 1 3.95
C23 C 2 0.1822(3) 0.29928(2) 0.51347(4) 1 3.95
H23 H 2 0.1456(3) 0.360866(18) 0.496632(18) 1 3.95
C24 C 2 0.2924(3) 0.35995(19) 0.39317(7) 1 3.95
C25 C 2 0.4542(3) 0.12173(7) 0.70557(4) 1 3.95
H25A H 2 0.4046(3) 0.15137(6) 0.739539(11) 1 3.95
H25B H 2 0.4747(3) 0.17751(5) 0.66280(5) 1 3.95
H25C H 2 0.5044(3) 0.101211(12) 0.749690(14) 1 3.95
C26 C 2 0.4219(3) 0.02141(3) 0.65124(8) 1 3.95
C27 C 2 0.3418(3) -0.08686(8) 0.55265(18) 1 3.95
C28 C 2 0.2724(3) -0.13251(10) 0.4832(2) 1 3.95
C29 C 2 0.2150(3) -0.06671(12) 0.4243(2) 1 3.95
H29 H 2 0.2182(3) 0.01102(12) 0.42800(19) 1 3.95
C30 C 2 0.1526(4) -0.11827(15) 0.3595(3) 1 3.95
H30 H 2 0.1143(4) -0.07327(16) 0.3204(3) 1 3.95
C31 C 2 0.2006(4) -0.29240(13) 0.4076(4) 1 3.95
H31 H 2 0.1960(4) -0.36982(13) 0.4024(4) 1 3.95
C32 C 2 0.2646(4) -0.24815(11) 0.4739(3) 1 3.95
H32 H 2 0.3019(4) -0.29522(9) 0.5121(3) 1 3.95
N5 N 2 0.3477(3) 0.02050(5) 0.58696(12) 1 3.95
N6 N 2 0.4583(3) -0.07860(5) 0.65527(12) 1 3.95
N7 N 2 0.4088(3) -0.14829(8) 0.59375(18) 1 3.95
N8 N 2 0.1453(4) -0.22899(15) 0.3508(4) 1 3.95
O5 O 2 0.0165(3) 0.16495(18) 0.6408(2) 1 3.95
O6 O 2 0.0536(3) 0.34378(18) 0.66046(9) 1 3.95
O7 O 2 0.3731(3) 0.3459(3) 0.36670(10) 1 3.95
O8 O 2 0.2382(3) 0.43205(19) 0.35957(8) 1 3.95
O9 O 2 0.1150(11) -0.470(2) 0.2334(14) 1 3.95
O10 O 2 0.3374(11) 0.542(2) 0.2486(12) 1 3.95

# It was not possible to generate estimated standard deviations 
# for the given bond lengths.

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
C1 O1 1.24320 1_555 1_555
C1 O2 1.24540 1_555 1_555
C1 C2 1.51440 1_555 1_555
C2 C7 1.37880 1_555 1_555
C2 C3 1.39990 1_555 1_555
C3 H3 0.92990 1_555 1_555
C3 C4 1.38320 1_555 1_555
C4 C5 1.38450 1_555 1_555
C4 N1 1.44360 1_555 1_555
C5 H5 0.92960 1_555 1_555
C5 C6 1.38770 1_555 1_555
C6 C7 1.39177 1_555 1_555
C6 C8 1.50680 1_555 1_555
C7 H7 0.93010 1_555 1_555
C8 O3 1.24170 1_555 1_555
C8 O4 1.26710 1_555 1_555
C9 H9C 0.95950 1_555 1_555
C9 H9A 0.95960 1_555 1_555
C9 H9B 0.96130 1_555 1_555
C9 C10 1.48340 1_555 1_555
C10 N2 1.30510 1_555 1_555
C10 N1 1.36640 1_555 1_555
C11 N3 1.32380 1_555 1_555
C11 N1 1.37140 1_555 1_555
C11 C12 1.46820 1_555 1_555
C12 C13 1.38470 1_555 1_555
C12 C16 1.39050 1_555 1_555
C13 H13 0.93000 1_555 1_555
C13 C14 1.39200 1_555 1_555
C14 H14 0.93010 1_555 1_555
C14 N4 1.33130 1_555 1_555
C15 H15 0.92960 1_555 1_555
C15 N4 1.33621 1_555 1_555
C15 C16 1.38220 1_555 1_555
C16 H16 0.93090 1_555 1_555
Cu1 O1 1.86710 1_555 1_555
Cu1 N8 1.94409 1_555 1_555
Cu1 O5 2.01442 1_555 2_546
Cu1 N4 2.05321 1_555 2_545
Cu1 O9 2.22233 1_555 1_555
Cu1 O6 2.73966 1_555 2_546
Cu2 O3 1.86462 1_555 2_655
Cu2 N2 1.95764 1_555 1_555
Cu2 O7 2.02532 1_555 1_555
Cu2 N6 2.08824 1_555 2_656
Cu2 O10 2.42029 1_555 1_555
Cu2 O4 3.04212 1_555 2_655
N2 N3 1.37389 1_555 1_555
C17 O6 1.24310 1_555 1_555
C17 O5 1.24630 1_555 1_555
C17 C18 1.51410 1_555 1_555
C18 C23 1.37960 1_555 1_555
C18 C19 1.40030 1_555 1_555
C19 H19 0.92980 1_555 1_555
C19 C20 1.38160 1_555 1_555
C20 C21 1.38450 1_555 1_555
C20 N5 1.44430 1_555 1_555
C21 H21 0.92950 1_555 1_555
C21 C22 1.38860 1_555 1_555
C22 C23 1.39306 1_555 1_555
C22 C24 1.50520 1_555 1_555
C23 H23 0.92970 1_555 1_555
C24 O8 1.24120 1_555 1_555
C24 O7 1.26700 1_555 1_555
C25 H25A 0.96010 1_555 1_555
C25 H25B 0.96020 1_555 1_555
C25 H25C 0.96120 1_555 1_555
C25 C26 1.48350 1_555 1_555
C26 N6 1.30590 1_555 1_555
C26 N5 1.36550 1_555 1_555
C27 N7 1.32370 1_555 1_555
C27 N5 1.37140 1_555 1_555
C27 C28 1.46810 1_555 1_555
C28 C29 1.38540 1_555 1_555
C28 C32 1.39090 1_555 1_555
C29 H29 0.93050 1_555 1_555
C29 C30 1.39170 1_555 1_555
C30 H30 0.93040 1_555 1_555
C30 N8 1.33120 1_555 1_555
C31 H31 0.92940 1_555 1_555
C31 N8 1.33606 1_555 1_555
C31 C32 1.38260 1_555 1_555
C32 H32 0.92980 1_555 1_555
N6 N7 1.37424 1_555 1_555


_chemical_properties_physical    Moisture-sensitive,Hygroscopic
_refine_special_details          'powder diffraction data'
