# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_as
_database_code_depnum_ccdc_archive 'CCDC 1533269'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 Cu N2 O4'
_chemical_formula_weight         307.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cu Cu 0.3201 1.2651 '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'

_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                   10.915(10)
_cell_length_b                   11.321(10)
_cell_length_c                   14.814(12)
_cell_angle_alpha                90
_cell_angle_beta                 109.602(13)
_cell_angle_gamma                90
_cell_volume                     1724(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2328
_cell_measurement_theta_min      2.29
_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    1.185
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.274
_shelx_estimated_absorpt_T_min   0.883
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11191
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.981
_diffrn_reflns_theta_max         25.044
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             3042
_reflns_number_gt                2147
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.2000P)²+1.9000P]
 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         3042
_refine_ls_number_parameters     173
_refine_ls_number_restraints     186
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0979
_refine_ls_wR_factor_ref         0.3139
_refine_ls_wR_factor_gt          0.2912
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.163
_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 0.90420(8) 0.58356(8) -0.02287(7) 0.0258(4) Uani 1 1 d . U . . .
O1 O 0.8197(6) 0.4815(5) 0.0463(5) 0.0418(14) Uani 1 1 d . U . . .
N2 N 0.2486(7) 0.2895(7) 0.0586(6) 0.0391(16) Uani 1 1 d . U . . .
C10 C 0.3747(9) 0.3293(9) 0.0891(6) 0.0403(19) Uani 1 1 d . U . . .
H10 H 0.3994 0.4083 0.0929 0.048 Uiso 1 1 calc R U . . .
N1 N 0.4566(7) 0.2375(6) 0.1124(6) 0.0354(15) Uani 1 1 d . U . . .
C6 C 0.5981(9) 0.2414(7) 0.1479(6) 0.0307(16) Uani 1 1 d . U . . .
C5 C 0.6636(9) 0.1768(10) 0.2253(7) 0.047(2) Uani 1 1 d . U . . .
H5 H 0.6188 0.1307 0.2559 0.056 Uiso 1 1 calc R U . . .
O3 O 0.9824(6) 0.1512(6) 0.3984(5) 0.0463(16) Uani 1 1 d . U . . .
O4 O 0.8196(6) 0.0147(6) 0.3621(5) 0.0436(15) Uani 1 1 d . U . . .
C8 C 0.8750(8) 0.1091(8) 0.3474(7) 0.0372(18) Uani 1 1 d . U . . .
O2 O 0.9803(6) 0.3466(6) 0.0884(5) 0.0470(16) Uani 1 1 d . U . . .
C1 C 0.8718(9) 0.3881(8) 0.0869(7) 0.0385(18) Uani 1 1 d . U . . .
C7 C 0.6608(9) 0.3114(9) 0.1004(7) 0.048(2) Uani 1 1 d . U . . .
H7 H 0.6146 0.3550 0.0465 0.058 Uiso 1 1 calc R U . . .
C3 C 0.8634(8) 0.2485(7) 0.2139(6) 0.0303(17) Uani 1 1 d . U . . .
H3 H 0.9538 0.2501 0.2370 0.036 Uiso 1 1 calc R U . . .
C2 C 0.8007(9) 0.3137(9) 0.1378(7) 0.0415(18) Uani 1 1 d . U . . .
C4 C 0.7998(8) 0.1793(9) 0.2595(7) 0.0407(19) Uani 1 1 d . U . . .
C9 C 0.3825(9) 0.1381(11) 0.0966(8) 0.057(2) Uani 1 1 d . U . . .
H9 H 0.4102 0.0600 0.1059 0.068 Uiso 1 1 calc R U . . .
C11 C 0.2506(9) 0.1824(10) 0.0621(8) 0.051(2) Uani 1 1 d . U . . .
C12 C 0.1194(6) 0.1007(5) 0.0317(5) 0.0123(13) Uani 1 1 d . U . . .
H12A H 0.0917 0.0900 0.0862 0.018 Uiso 1 1 calc R U . . .
H12B H 0.1379 0.0252 0.0097 0.018 Uiso 1 1 calc R U . . .
H12C H 0.0517 0.1390 -0.0187 0.018 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
Cu1 O1 1.967(6) . ?
Cu1 O4 1.984(6) 4_565 ?
Cu1 O2 1.994(6) 3_765 ?
Cu1 O3 1.996(6) 2_755 ?
Cu1 N2 2.129(7) 3_665 ?
Cu1 Cu1 2.732(3) 3_765 ?
O1 C1 1.254(11) . ?
N2 C11 1.214(14) . ?
N2 C10 1.372(12) . ?
N2 Cu1 2.129(7) 3_665 ?
C10 N1 1.340(12) . ?
C10 H10 0.9300 . ?
N1 C9 1.359(13) . ?
N1 C6 1.455(12) . ?
C6 C5 1.346(13) . ?
C6 C7 1.384(13) . ?
C5 C4 1.401(13) . ?
C5 H5 0.9300 . ?
O3 C8 1.256(10) . ?
O3 Cu1 1.996(6) 2_745 ?
O4 C8 1.283(11) . ?
O4 Cu1 1.984(6) 4_566 ?
C8 C4 1.511(12) . ?
O2 C1 1.267(11) . ?
O2 Cu1 1.994(6) 3_765 ?
C1 C2 1.508(13) . ?
C7 C2 1.439(13) . ?
C7 H7 0.9300 . ?
C3 C2 1.329(12) . ?
C3 C4 1.366(12) . ?
C3 H3 0.9300 . ?
C9 C11 1.447(14) . ?
C9 H9 0.9300 . ?
C11 C12 1.635(11) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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 O4 87.3(3) . 4_565 ?
O1 Cu1 O2 165.9(3) . 3_765 ?
O4 Cu1 O2 89.6(3) 4_565 3_765 ?
O1 Cu1 O3 89.9(3) . 2_755 ?
O4 Cu1 O3 166.8(3) 4_565 2_755 ?
O2 Cu1 O3 90.0(3) 3_765 2_755 ?
O1 Cu1 N2 93.5(3) . 3_665 ?
O4 Cu1 N2 93.7(3) 4_565 3_665 ?
O2 Cu1 N2 100.5(3) 3_765 3_665 ?
O3 Cu1 N2 99.3(3) 2_755 3_665 ?
O1 Cu1 Cu1 85.28(19) . 3_765 ?
O4 Cu1 Cu1 85.52(19) 4_565 3_765 ?
O2 Cu1 Cu1 80.7(2) 3_765 3_765 ?
O3 Cu1 Cu1 81.43(19) 2_755 3_765 ?
N2 Cu1 Cu1 178.6(2) 3_665 3_765 ?
C1 O1 Cu1 121.9(6) . . ?
C11 N2 C10 108.2(8) . . ?
C11 N2 Cu1 133.3(6) . 3_665 ?
C10 N2 Cu1 118.4(6) . 3_665 ?
N1 C10 N2 109.8(8) . . ?
N1 C10 H10 125.1 . . ?
N2 C10 H10 125.1 . . ?
C10 N1 C9 106.9(8) . . ?
C10 N1 C6 127.2(7) . . ?
C9 N1 C6 125.8(7) . . ?
C5 C6 C7 122.1(9) . . ?
C5 C6 N1 119.2(8) . . ?
C7 C6 N1 118.7(8) . . ?
C6 C5 C4 119.6(9) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C8 O3 Cu1 125.0(6) . 2_745 ?
C8 O4 Cu1 120.2(5) . 4_566 ?
O3 C8 O4 127.8(8) . . ?
O3 C8 C4 116.5(8) . . ?
O4 C8 C4 115.7(8) . . ?
C1 O2 Cu1 125.7(6) . 3_765 ?
O1 C1 O2 126.3(8) . . ?
O1 C1 C2 118.9(8) . . ?
O2 C1 C2 114.7(8) . . ?
C6 C7 C2 117.2(9) . . ?
C6 C7 H7 121.4 . . ?
C2 C7 H7 121.4 . . ?
C2 C3 C4 122.4(8) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C3 C2 C7 119.7(9) . . ?
C3 C2 C1 122.0(8) . . ?
C7 C2 C1 118.3(8) . . ?
C3 C4 C5 119.1(8) . . ?
C3 C4 C8 120.6(8) . . ?
C5 C4 C8 120.3(8) . . ?
N1 C9 C11 103.8(9) . . ?
N1 C9 H9 128.1 . . ?
C11 C9 H9 128.1 . . ?
N2 C11 C9 111.2(9) . . ?
N2 C11 C12 123.5(8) . . ?
C9 C11 C12 125.3(9) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N2 C10 N1 -0.1(11) . . . . ?
Cu1 N2 C10 N1 177.1(6) 3_665 . . . ?
N2 C10 N1 C9 0.1(11) . . . . ?
N2 C10 N1 C6 -179.9(8) . . . . ?
C10 N1 C6 C5 132.0(10) . . . . ?
C9 N1 C6 C5 -48.0(14) . . . . ?
C10 N1 C6 C7 -48.3(13) . . . . ?
C9 N1 C6 C7 131.7(11) . . . . ?
C7 C6 C5 C4 -0.2(15) . . . . ?
N1 C6 C5 C4 179.5(9) . . . . ?
Cu1 O3 C8 O4 -2.8(15) 2_745 . . . ?
Cu1 O3 C8 C4 175.5(6) 2_745 . . . ?
Cu1 O4 C8 O3 0.3(14) 4_566 . . . ?
Cu1 O4 C8 C4 -178.0(6) 4_566 . . . ?
Cu1 O1 C1 O2 -1.0(14) . . . . ?
Cu1 O1 C1 C2 -179.4(6) . . . . ?
Cu1 O2 C1 O1 -2.0(15) 3_765 . . . ?
Cu1 O2 C1 C2 176.5(6) 3_765 . . . ?
C5 C6 C7 C2 -0.7(14) . . . . ?
N1 C6 C7 C2 179.6(8) . . . . ?
C4 C3 C2 C7 -0.7(15) . . . . ?
C4 C3 C2 C1 -178.9(9) . . . . ?
C6 C7 C2 C3 1.1(15) . . . . ?
C6 C7 C2 C1 179.4(9) . . . . ?
O1 C1 C2 C3 -149.5(9) . . . . ?
O2 C1 C2 C3 31.8(14) . . . . ?
O1 C1 C2 C7 32.3(14) . . . . ?
O2 C1 C2 C7 -146.4(10) . . . . ?
C2 C3 C4 C5 -0.2(15) . . . . ?
C2 C3 C4 C8 -178.4(9) . . . . ?
C6 C5 C4 C3 0.6(16) . . . . ?
C6 C5 C4 C8 178.9(9) . . . . ?
O3 C8 C4 C3 29.0(14) . . . . ?
O4 C8 C4 C3 -152.5(9) . . . . ?
O3 C8 C4 C5 -149.2(10) . . . . ?
O4 C8 C4 C5 29.3(14) . . . . ?
C10 N1 C9 C11 0.0(12) . . . . ?
C6 N1 C9 C11 180.0(9) . . . . ?
C10 N2 C11 C9 0.2(13) . . . . ?
Cu1 N2 C11 C9 -176.5(7) 3_665 . . . ?
C10 N2 C11 C12 179.9(8) . . . . ?
Cu1 N2 C11 C12 3.2(16) 3_665 . . . ?
N1 C9 C11 N2 -0.1(13) . . . . ?
N1 C9 C11 C12 -179.9(9) . . . . ?

_refine_diff_density_max         1.599
_refine_diff_density_min         -1.091
_refine_diff_density_rms         0.202


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 -0.025 -0.009 -0.003 880 221 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


_shelxl_version_number           2013-2



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

data_as
_database_code_depnum_ccdc_archive 'CCDC 1533267'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H6 Cu N2 O4'
_chemical_formula_weight         293.72

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                   10.830(7)
_cell_length_b                   11.889(8)
_cell_length_c                   14.559(9)
_cell_angle_alpha                90
_cell_angle_beta                 109.594(8)
_cell_angle_gamma                90
_cell_volume                     1766.0(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2042
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      24.43

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.241
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9851
_diffrn_reflns_av_unetI/netI     0.1455
_diffrn_reflns_av_R_equivalents  0.0978
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.996
_diffrn_reflns_theta_max         25.043
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measured_fraction_theta_full 0.838
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_Laue_measured_fraction_full 0.838
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_point_group_measured_fraction_full 0.838
_reflns_number_total             2672
_reflns_number_gt                1627
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1509P)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         2672
_refine_ls_number_parameters     163
_refine_ls_number_restraints     261
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0899
_refine_ls_wR_factor_ref         0.2592
_refine_ls_wR_factor_gt          0.2465
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      0.992
_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 0.6202(9) 0.3862(8) 0.6495(7) 0.0295(18) Uani 1 1 d . U . . .
C2 C 0.6903(9) 0.3144(8) 0.7337(8) 0.0328(19) Uani 1 1 d . U . . .
C3 C 0.6266(9) 0.2488(6) 0.7824(7) 0.0182(17) Uani 1 1 d . U . . .
H3 H 0.5356 0.2508 0.7630 0.022 Uiso 1 1 calc R U . . .
C4 C 0.6936(9) 0.1823(8) 0.8573(8) 0.0317(19) Uani 1 1 d . U . . .
C5 C 0.8261(9) 0.1798(8) 0.8899(8) 0.033(2) Uani 1 1 d . U . . .
H5 H 0.8711 0.1319 0.9406 0.039 Uiso 1 1 calc R U . . .
C6 C 0.8932(8) 0.2483(6) 0.8479(8) 0.0184(17) Uani 1 1 d . U . . .
C7 C 0.8283(10) 0.3167(8) 0.7679(9) 0.037(2) Uani 1 1 d . U . . .
H7 H 0.8745 0.3618 0.7385 0.045 Uiso 1 1 calc R U . . .
C8 C 0.6165(9) 0.1104(8) 0.9092(7) 0.0254(17) Uani 1 1 d . U . . .
C9 C 1.1154(10) 0.3381(9) 0.8946(10) 0.044(2) Uani 1 1 d . U . . .
H9 H 1.0899 0.4123 0.8786 0.053 Uiso 1 1 calc R U . . .
C10 C 1.1136(8) 0.1563(7) 0.9073(7) 0.0234(18) Uani 1 1 d . U . . .
H10 H 1.0862 0.0817 0.9034 0.028 Uiso 1 1 calc R U . . .
C11 C 1.2385(9) 0.3028(8) 0.9314(10) 0.044(2) Uani 1 1 d . U . . .
H11 H 1.3126 0.3483 0.9505 0.053 Uiso 1 1 calc R U . . .
Cu1 Cu 0.40048(9) 0.07457(8) 0.97527(8) 0.0174(4) Uani 1 1 d . U . . .
N1 N 1.0311(7) 0.2486(5) 0.8839(7) 0.0196(15) Uani 1 1 d . U . . .
N2 N 1.2377(7) 0.1899(6) 0.9362(6) 0.0256(16) Uani 1 1 d . U . . .
O1 O 0.6741(7) 0.4722(6) 0.6356(6) 0.0382(17) Uani 1 1 d . U . . .
O2 O 0.5062(6) 0.3495(6) 0.5962(6) 0.0388(17) Uani 1 1 d . U . . .
O3 O 0.5115(6) 0.1445(6) 0.9050(5) 0.0301(15) Uani 1 1 d . U . . .
O4 O 0.6755(7) 0.0240(6) 0.9499(5) 0.0354(16) Uani 1 1 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 1.227(12) . ?
C1 O2 1.294(11) . ?
C1 C2 1.477(14) . ?
C2 C3 1.384(13) . ?
C2 C7 1.408(13) . ?
C3 C4 1.346(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.352(13) . ?
C4 C8 1.556(13) . ?
C5 C6 1.364(13) . ?
C5 H5 0.9300 . ?
C6 C7 1.402(14) . ?
C6 N1 1.407(11) . ?
C7 H7 0.9300 . ?
C8 O3 1.189(11) . ?
C8 O4 1.249(11) . ?
C9 C11 1.328(14) . ?
C9 N1 1.377(12) . ?
C9 H9 0.9300 . ?
C10 N2 1.328(11) . ?
C10 N1 1.384(10) . ?
C10 H10 0.9300 . ?
C11 N2 1.344(13) . ?
C11 H11 0.9300 . ?
Cu1 O4 1.959(7) 3_657 ?
Cu1 O1 1.965(7) 2_646 ?
Cu1 O2 1.968(7) 4_566 ?
Cu1 O3 2.002(6) . ?
Cu1 N2 2.154(7) 1_455 ?
Cu1 Cu1 2.696(2) 3_657 ?
N2 Cu1 2.154(7) 1_655 ?
O1 Cu1 1.965(7) 2_656 ?
O2 Cu1 1.968(7) 4_565 ?
O4 Cu1 1.959(7) 3_657 ?

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 126.3(9) . . ?
O1 C1 C2 118.6(9) . . ?
O2 C1 C2 115.1(8) . . ?
C3 C2 C7 118.8(9) . . ?
C3 C2 C1 123.1(8) . . ?
C7 C2 C1 118.1(9) . . ?
C4 C3 C2 121.4(9) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 121.1(9) . . ?
C3 C4 C8 119.0(8) . . ?
C5 C4 C8 119.8(9) . . ?
C4 C5 C6 119.5(9) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 121.6(9) . . ?
C5 C6 N1 119.5(8) . . ?
C7 C6 N1 118.8(8) . . ?
C6 C7 C2 117.4(9) . . ?
C6 C7 H7 121.3 . . ?
C2 C7 H7 121.3 . . ?
O3 C8 O4 129.3(9) . . ?
O3 C8 C4 116.6(8) . . ?
O4 C8 C4 114.2(8) . . ?
C11 C9 N1 109.8(9) . . ?
C11 C9 H9 125.1 . . ?
N1 C9 H9 125.1 . . ?
N2 C10 N1 109.9(7) . . ?
N2 C10 H10 125.0 . . ?
N1 C10 H10 125.0 . . ?
C9 C11 N2 108.3(8) . . ?
C9 C11 H11 125.8 . . ?
N2 C11 H11 125.8 . . ?
O4 Cu1 O1 87.3(3) 3_657 2_646 ?
O4 Cu1 O2 90.2(3) 3_657 4_566 ?
O1 Cu1 O2 166.9(3) 2_646 4_566 ?
O4 Cu1 O3 165.6(3) 3_657 . ?
O1 Cu1 O3 89.4(3) 2_646 . ?
O2 Cu1 O3 89.9(3) 4_566 . ?
O4 Cu1 N2 93.9(3) 3_657 1_455 ?
O1 Cu1 N2 95.9(3) 2_646 1_455 ?
O2 Cu1 N2 97.1(3) 4_566 1_455 ?
O3 Cu1 N2 100.3(3) . 1_455 ?
O4 Cu1 Cu1 84.6(2) 3_657 3_657 ?
O1 Cu1 Cu1 83.3(2) 2_646 3_657 ?
O2 Cu1 Cu1 83.6(2) 4_566 3_657 ?
O3 Cu1 Cu1 81.1(2) . 3_657 ?
N2 Cu1 Cu1 178.3(2) 1_455 3_657 ?
C9 N1 C10 103.7(8) . . ?
C9 N1 C6 128.7(7) . . ?
C10 N1 C6 127.4(6) . . ?
C10 N2 C11 107.9(7) . . ?
C10 N2 Cu1 122.9(6) . 1_655 ?
C11 N2 Cu1 129.1(6) . 1_655 ?
C1 O1 Cu1 124.4(6) . 2_656 ?
C1 O2 Cu1 122.3(6) . 4_565 ?
C8 O3 Cu1 124.0(6) . . ?
C8 O4 Cu1 120.8(6) . 3_657 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 150.3(10) . . . . ?
O2 C1 C2 C3 -30.6(14) . . . . ?
O1 C1 C2 C7 -27.2(15) . . . . ?
O2 C1 C2 C7 151.9(10) . . . . ?
C7 C2 C3 C4 -4.3(15) . . . . ?
C1 C2 C3 C4 178.3(9) . . . . ?
C2 C3 C4 C5 2.3(16) . . . . ?
C2 C3 C4 C8 -179.9(9) . . . . ?
C3 C4 C5 C6 1.8(16) . . . . ?
C8 C4 C5 C6 -176.0(9) . . . . ?
C4 C5 C6 C7 -3.7(16) . . . . ?
C4 C5 C6 N1 177.9(9) . . . . ?
C5 C6 C7 C2 1.6(16) . . . . ?
N1 C6 C7 C2 180.0(9) . . . . ?
C3 C2 C7 C6 2.3(15) . . . . ?
C1 C2 C7 C6 179.9(9) . . . . ?
C3 C4 C8 O3 -25.6(14) . . . . ?
C5 C4 C8 O3 152.2(10) . . . . ?
C3 C4 C8 O4 154.5(9) . . . . ?
C5 C4 C8 O4 -27.7(14) . . . . ?
N1 C9 C11 N2 6.0(15) . . . . ?
C11 C9 N1 C10 -6.1(14) . . . . ?
C11 C9 N1 C6 179.9(11) . . . . ?
N2 C10 N1 C9 4.0(12) . . . . ?
N2 C10 N1 C6 178.1(9) . . . . ?
C5 C6 N1 C9 -141.9(12) . . . . ?
C7 C6 N1 C9 39.7(16) . . . . ?
C5 C6 N1 C10 45.4(15) . . . . ?
C7 C6 N1 C10 -133.0(11) . . . . ?
N1 C10 N2 C11 -0.6(12) . . . . ?
N1 C10 N2 Cu1 -177.9(7) . . . 1_655 ?
C9 C11 N2 C10 -3.3(13) . . . . ?
C9 C11 N2 Cu1 173.8(9) . . . 1_655 ?
O2 C1 O1 Cu1 -1.6(15) . . . 2_656 ?
C2 C1 O1 Cu1 177.4(7) . . . 2_656 ?
O1 C1 O2 Cu1 3.4(15) . . . 4_565 ?
C2 C1 O2 Cu1 -175.7(6) . . . 4_565 ?
O4 C8 O3 Cu1 5.4(16) . . . . ?
C4 C8 O3 Cu1 -174.5(6) . . . . ?
O3 C8 O4 Cu1 -2.8(15) . . . 3_657 ?
C4 C8 O4 Cu1 177.0(6) . . . 3_657 ?

_refine_diff_density_max         1.673
_refine_diff_density_min         -0.930
_refine_diff_density_rms         0.179

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 -0.045 -0.007 0.490 952 197 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


_shelxl_version_number           2013-2



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

data_bs
_database_code_depnum_ccdc_archive 'CCDC 1533270'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 Cu N2 O4'
_chemical_formula_weight         321.77

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                   10.93(3)
_cell_length_b                   13.71(4)
_cell_length_c                   13.47(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.86(3)
_cell_angle_gamma                90
_cell_volume                     1874(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1077
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      20.55

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_F_000             652
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.175
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12914
_diffrn_reflns_av_unetI/netI     0.2159
_diffrn_reflns_av_R_equivalents  0.1537
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.205
_diffrn_reflns_theta_max         26.045
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3597
_reflns_number_gt                1575
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1432P)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         3597
_refine_ls_number_parameters     173
_refine_ls_number_restraints     296
_refine_ls_R_factor_all          0.1831
_refine_ls_R_factor_gt           0.1122
_refine_ls_wR_factor_ref         0.3116
_refine_ls_wR_factor_gt          0.2809
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.017
_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
C1 C 0.3906(11) 0.8809(9) 0.3475(9) 0.047(3) Uani 1 1 d . U . . .
C2 C 0.3241(10) 0.8019(8) 0.2683(8) 0.044(2) Uani 1 1 d . U . . .
C3 C 0.1882(11) 0.7940(9) 0.2384(9) 0.063(3) Uani 1 1 d . U . . .
H3 H 0.1400 0.8373 0.2627 0.075 Uiso 1 1 calc R U . . .
C4 C 0.1280(12) 0.7161(10) 0.1686(11) 0.071(3) Uani 1 1 d . U . . .
C5 C 0.1875(12) 0.6576(10) 0.1230(10) 0.067(3) Uani 1 1 d . U . . .
H5 H 0.1406 0.6122 0.0716 0.081 Uiso 1 1 calc R U . . .
C6 C 0.3284(9) 0.6671(8) 0.1564(8) 0.042(2) Uani 1 1 d . U . . .
C7 C 0.3918(10) 0.7385(8) 0.2272(8) 0.044(3) Uani 1 1 d . U . . .
H7 H 0.4827 0.7447 0.2483 0.052 Uiso 1 1 calc R U . . .
C8 C 0.3943(10) 0.6000(9) 0.1043(9) 0.046(3) Uani 1 1 d . U . . .
C10 C -0.2349(9) 0.7432(8) 0.0367(11) 0.169(7) Uani 1 1 d G U . . .
H10 H -0.3141 0.7733 -0.0036 0.203 Uiso 1 1 calc R U . . .
N2 N -0.2207(7) 0.6517(6) 0.0892(8) 0.063(3) Uani 1 1 d G U . . .
C11 C -0.0839(9) 0.6326(7) 0.1414(9) 0.115(5) Uani 1 1 d G U . . .
N1 N -0.0136(7) 0.7124(9) 0.1211(11) 0.117(4) Uani 1 1 d G U . . .
C9 C -0.1069(12) 0.7807(8) 0.0564(13) 0.177(7) Uani 1 1 d G U . . .
H9 H -0.0875 0.8397 0.0313 0.213 Uiso 1 1 calc R U . . .
O1 O 0.3295(7) 0.9574(5) 0.3531(6) 0.0482(19) Uani 1 1 d . U . . .
O2 O 0.5086(7) 0.8598(5) 0.4118(6) 0.053(2) Uani 1 1 d . U . . .
O3 O 0.5138(6) 0.6245(5) 0.1171(6) 0.0465(19) Uani 1 1 d . U . . .
O4 O 0.3342(7) 0.5293(5) 0.0527(6) 0.0486(19) Uani 1 1 d . U . . .
Cu1 Cu 0.38937(11) 1.05785(9) 0.46271(10) 0.0349(5) Uani 1 1 d . U . . .
C12 C -0.017(2) 0.5316(16) 0.208(2) 0.165(7) Uani 1 1 d . U . . .
H12A H 0.0598 0.5532 0.2675 0.198 Uiso 1 1 calc R U . . .
H12B H -0.0794 0.5086 0.2384 0.198 Uiso 1 1 calc R U . . .
C13 C 0.029(3) 0.4367(19) 0.164(2) 0.195(10) Uani 1 1 d . U . . .
H13A H 0.1126 0.4157 0.2141 0.292 Uiso 1 1 calc R U . . .
H13B H 0.0364 0.4513 0.0965 0.292 Uiso 1 1 calc R U . . .
H13C H -0.0350 0.3858 0.1538 0.292 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 1.262(13) . ?
C1 O2 1.291(12) . ?
C1 C2 1.504(15) . ?
C2 C7 1.384(13) . ?
C2 C3 1.391(15) . ?
C3 C4 1.412(16) . ?
C3 H3 0.9300 . ?
C4 C5 1.320(16) . ?
C4 N1 1.439(14) . ?
C5 C6 1.441(15) . ?
C5 H5 0.9300 . ?
C6 C7 1.362(14) . ?
C6 C8 1.495(14) . ?
C7 H7 0.9300 . ?
C8 O4 1.230(12) . ?
C8 O3 1.297(12) . ?
C10 C9 1.4200 . ?
C10 N2 1.4200 . ?
C10 H10 0.9300 . ?
N2 C11 1.4200 . ?
N2 Cu1 2.142(8) 2_545 ?
C11 N1 1.4200 . ?
C11 C12 1.66(2) . ?
N1 C9 1.4200 . ?
C9 H9 0.9300 . ?
O1 Cu1 1.945(8) . ?
O2 Cu1 1.993(8) 3_676 ?
O3 Cu1 1.989(8) 2_645 ?
O4 Cu1 1.951(8) 4_575 ?
Cu1 O4 1.951(8) 4_576 ?
Cu1 O3 1.989(8) 2_655 ?
Cu1 O2 1.993(8) 3_676 ?
Cu1 N2 2.14(3) 2 ?
Cu1 Cu1 2.751(6) 3_676 ?
C12 C13 1.59(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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 124.4(10) . . ?
O1 C1 C2 120.9(10) . . ?
O2 C1 C2 114.5(10) . . ?
C7 C2 C3 120.5(10) . . ?
C7 C2 C1 123.1(9) . . ?
C3 C2 C1 116.4(10) . . ?
C2 C3 C4 115.7(11) . . ?
C2 C3 H3 122.1 . . ?
C4 C3 H3 122.1 . . ?
C5 C4 C3 125.5(12) . . ?
C5 C4 N1 114.0(12) . . ?
C3 C4 N1 118.7(11) . . ?
C4 C5 C6 117.0(11) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 H5 121.5 . . ?
C7 C6 C5 119.3(10) . . ?
C7 C6 C8 124.2(9) . . ?
C5 C6 C8 116.4(9) . . ?
C6 C7 C2 121.5(10) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
O4 C8 O3 125.5(10) . . ?
O4 C8 C6 120.0(9) . . ?
O3 C8 C6 114.6(9) . . ?
C9 C10 N2 108.0 . . ?
C9 C10 H10 126.0 . . ?
N2 C10 H10 126.0 . . ?
C11 N2 C10 108.0 . . ?
C11 N2 Cu1 132.2(6) . 2_545 ?
C10 N2 Cu1 116.5(6) . 2_545 ?
N1 C11 N2 108.0 . . ?
N1 C11 C12 125.7(11) . . ?
N2 C11 C12 126.1(11) . . ?
C11 N1 C9 108.0 . . ?
C11 N1 C4 120.8(11) . . ?
C9 N1 C4 131.1(11) . . ?
C10 C9 N1 108.0 . . ?
C10 C9 H9 126.0 . . ?
N1 C9 H9 126.0 . . ?
C1 O1 Cu1 126.7(7) . . ?
C1 O2 Cu1 123.1(7) . 3_676 ?
C8 O3 Cu1 121.4(7) . 2_645 ?
C8 O4 Cu1 127.5(7) . 4_575 ?
O1 Cu1 O4 86.8(4) . 4_576 ?
O1 Cu1 O3 90.6(4) . 2_655 ?
O4 Cu1 O3 165.2(3) 4_576 2_655 ?
O1 Cu1 O2 165.6(3) . 3_676 ?
O4 Cu1 O2 91.4(4) 4_576 3_676 ?
O3 Cu1 O2 87.5(4) 2_655 3_676 ?
O1 Cu1 N2 100(2) . 2 ?
O4 Cu1 N2 98.2(14) 4_576 2 ?
O3 Cu1 N2 96.6(14) 2_655 2 ?
O2 Cu1 N2 95(2) 3_676 2 ?
O1 Cu1 Cu1 82.6(3) . 3_676 ?
O4 Cu1 Cu1 81.6(3) 4_576 3_676 ?
O3 Cu1 Cu1 83.7(3) 2_655 3_676 ?
O2 Cu1 Cu1 83.0(3) 3_676 3_676 ?
N2 Cu1 Cu1 178(2) 2 3_676 ?
C13 C12 C11 128(2) . . ?
C13 C12 H12A 105.3 . . ?
C11 C12 H12A 105.3 . . ?
C13 C12 H12B 105.3 . . ?
C11 C12 H12B 105.3 . . ?
H12A C12 H12B 106.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C7 152.9(11) . . . . ?
O2 C1 C2 C7 -31.8(15) . . . . ?
O1 C1 C2 C3 -28.0(16) . . . . ?
O2 C1 C2 C3 147.3(11) . . . . ?
C7 C2 C3 C4 2.5(18) . . . . ?
C1 C2 C3 C4 -176.6(10) . . . . ?
C2 C3 C4 C5 -7(2) . . . . ?
C2 C3 C4 N1 -170.4(12) . . . . ?
C3 C4 C5 C6 7(2) . . . . ?
N1 C4 C5 C6 171.7(12) . . . . ?
C4 C5 C6 C7 -3.9(18) . . . . ?
C4 C5 C6 C8 179.8(12) . . . . ?
C5 C6 C7 C2 0.4(17) . . . . ?
C8 C6 C7 C2 176.3(10) . . . . ?
C3 C2 C7 C6 0.2(18) . . . . ?
C1 C2 C7 C6 179.3(10) . . . . ?
C7 C6 C8 O4 170.2(11) . . . . ?
C5 C6 C8 O4 -13.7(16) . . . . ?
C7 C6 C8 O3 -11.0(16) . . . . ?
C5 C6 C8 O3 165.1(10) . . . . ?
C9 C10 N2 C11 0.0 . . . . ?
C9 C10 N2 Cu1 -162.1(7) . . . 2_545 ?
C10 N2 C11 N1 0.0 . . . . ?
Cu1 N2 C11 N1 158.2(9) 2_545 . . . ?
C10 N2 C11 C12 -176.2(16) . . . . ?
Cu1 N2 C11 C12 -18.1(17) 2_545 . . . ?
N2 C11 N1 C9 0.0 . . . . ?
C12 C11 N1 C9 176.2(16) . . . . ?
N2 C11 N1 C4 176.8(13) . . . . ?
C12 C11 N1 C4 -7.0(17) . . . . ?
C5 C4 N1 C11 76.0(15) . . . . ?
C3 C4 N1 C11 -118.5(13) . . . . ?
C5 C4 N1 C9 -108.1(15) . . . . ?
C3 C4 N1 C9 57.4(19) . . . . ?
N2 C10 C9 N1 0.0 . . . . ?
C11 N1 C9 C10 0.0 . . . . ?
C4 N1 C9 C10 -176.3(15) . . . . ?
O2 C1 O1 Cu1 -4.5(17) . . . . ?
C2 C1 O1 Cu1 170.3(7) . . . . ?
O1 C1 O2 Cu1 3.8(16) . . . 3_676 ?
C2 C1 O2 Cu1 -171.2(7) . . . 3_676 ?
O4 C8 O3 Cu1 7.9(16) . . . 2_645 ?
C6 C8 O3 Cu1 -170.8(7) . . . 2_645 ?
O3 C8 O4 Cu1 -7.4(17) . . . 4_575 ?
C6 C8 O4 Cu1 171.2(7) . . . 4_575 ?
N1 C11 C12 C13 -84(2) . . . . ?
N2 C11 C12 C13 92(2) . . . . ?

_refine_diff_density_max         1.810
_refine_diff_density_min         -0.958
_refine_diff_density_rms         0.185


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 -0.039 -0.023 -0.013 845 209 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


_shelxl_version_number           2013-2



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

data_as
_database_code_depnum_ccdc_archive 'CCDC 1533268'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 Cu N2 O4'
_chemical_formula_weight         307.74

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   12.678(5)
_cell_length_b                   14.408(5)
_cell_length_c                   20.225(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3694(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1632
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.68

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.189
_shelx_estimated_absorpt_T_min   0.797
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20783
_diffrn_reflns_av_unetI/netI     0.1431
_diffrn_reflns_av_R_equivalents  0.2490
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.014
_diffrn_reflns_theta_max         23.148
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.782
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.782
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.782
_reflns_number_total             2618
_reflns_number_gt                1463
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1535P)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         2618
_refine_ls_number_parameters     173
_refine_ls_number_restraints     282
_refine_ls_R_factor_all          0.1681
_refine_ls_R_factor_gt           0.1032
_refine_ls_wR_factor_ref         0.2639
_refine_ls_wR_factor_gt          0.2291
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      0.975
_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 0.3859(9) 0.5167(7) 0.3026(5) 0.028(2) Uani 1 1 d . U . . .
C2 C 0.3199(9) 0.4475(8) 0.3386(5) 0.032(2) Uani 1 1 d . U . . .
C3 C 0.2509(9) 0.3874(6) 0.3033(5) 0.029(2) Uani 1 1 d . U . . .
H3 H 0.2467 0.3905 0.2574 0.035 Uiso 1 1 calc R U . . .
C4 C 0.1918(9) 0.3261(8) 0.3371(5) 0.034(2) Uani 1 1 d . U . . .
C5 C 0.1964(9) 0.3205(9) 0.4070(5) 0.039(2) Uani 1 1 d . U . . .
H5 H 0.1542 0.2786 0.4299 0.047 Uiso 1 1 calc R U . . .
C6 C 0.2631(10) 0.3770(7) 0.4396(5) 0.038(2) Uani 1 1 d . U . . .
C7 C 0.3215(9) 0.4416(8) 0.4071(5) 0.039(2) Uani 1 1 d . U . . .
H7 H 0.3632 0.4826 0.4312 0.047 Uiso 1 1 calc R U . . .
C8 C 0.3597(9) 0.3640(8) 0.5473(5) 0.032(2) Uani 1 1 d . U . . .
C9 C 0.4697(10) 0.3595(10) 0.5201(6) 0.054(3) Uani 1 1 d . U . . .
H9A H 0.4933 0.4210 0.5094 0.082 Uiso 1 1 calc R U . . .
H9B H 0.4702 0.3218 0.4810 0.082 Uiso 1 1 calc R U . . .
H9C H 0.5159 0.3328 0.5526 0.082 Uiso 1 1 calc R U . . .
C10 C 0.2272(9) 0.3657(8) 0.6147(6) 0.043(3) Uani 1 1 d . U . . .
H10 H 0.1884 0.3634 0.6537 0.052 Uiso 1 1 calc R U . . .
C11 C 0.1848(10) 0.3743(8) 0.5536(6) 0.043(3) Uani 1 1 d . U . . .
H11 H 0.1140 0.3813 0.5428 0.052 Uiso 1 1 calc R U . . .
C15 C 0.1173(9) 0.2597(7) 0.3016(5) 0.027(2) Uani 1 1 d . U . . .
Cu1 Cu 0.43604(9) 0.63946(8) 0.19638(5) 0.0168(5) Uani 1 1 d . U . . .
N1 N 0.2703(7) 0.3703(6) 0.5103(4) 0.037(2) Uani 1 1 d . U . . .
N2 N 0.3353(6) 0.3608(6) 0.6113(4) 0.0281(19) Uani 1 1 d . U . . .
O1 O 0.3563(5) 0.5447(5) 0.2468(3) 0.0297(17) Uani 1 1 d . U . . .
O2 O 0.4664(6) 0.5423(5) 0.3341(3) 0.0336(19) Uani 1 1 d . U . . .
O3 O 0.0402(6) 0.2319(5) 0.3342(3) 0.0313(19) Uani 1 1 d . U . . .
O4 O 0.1424(5) 0.2386(5) 0.2441(3) 0.0306(18) Uani 1 1 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 1.256(12) . ?
C1 O2 1.258(12) . ?
C1 C2 1.491(14) . ?
C2 C7 1.390(14) . ?
C2 C3 1.423(13) . ?
C3 C4 1.345(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.417(14) . ?
C4 C15 1.522(14) . ?
C5 C6 1.348(15) . ?
C5 H5 0.9300 . ?
C6 C7 1.358(15) . ?
C6 N1 1.436(13) . ?
C7 H7 0.9300 . ?
C8 N2 1.332(13) . ?
C8 N1 1.362(13) . ?
C8 C9 1.500(16) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.353(16) . ?
C10 N2 1.374(14) . ?
C10 H10 0.9300 . ?
C11 N1 1.395(14) . ?
C11 H11 0.9300 . ?
C15 O4 1.244(12) . ?
C15 O3 1.245(12) . ?
Cu1 O2 1.966(7) 4_655 ?
Cu1 O3 1.975(7) 6_666 ?
Cu1 O1 1.982(7) . ?
Cu1 O4 1.990(7) 7_665 ?
Cu1 N2 2.142(8) 8_565 ?
Cu1 Cu1 2.708(2) 4_655 ?
N2 Cu1 2.142(8) 8_566 ?
O2 Cu1 1.966(7) 4_655 ?
O3 Cu1 1.975(7) 6_556 ?
O4 Cu1 1.990(7) 7_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 127.1(10) . . ?
O1 C1 C2 119.0(10) . . ?
O2 C1 C2 113.9(9) . . ?
C7 C2 C3 118.2(10) . . ?
C7 C2 C1 121.3(10) . . ?
C3 C2 C1 120.5(10) . . ?
C4 C3 C2 119.2(10) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.4(11) . . ?
C3 C4 C15 121.3(10) . . ?
C5 C4 C15 117.3(10) . . ?
C6 C5 C4 118.7(11) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C7 121.4(11) . . ?
C5 C6 N1 119.1(11) . . ?
C7 C6 N1 119.5(10) . . ?
C6 C7 C2 121.0(11) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
N2 C8 N1 110.1(9) . . ?
N2 C8 C9 124.8(10) . . ?
N1 C8 C9 125.0(9) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N2 110.8(10) . . ?
C11 C10 H10 124.6 . . ?
N2 C10 H10 124.6 . . ?
C10 C11 N1 105.2(11) . . ?
C10 C11 H11 127.4 . . ?
N1 C11 H11 127.4 . . ?
O4 C15 O3 128.1(10) . . ?
O4 C15 C4 115.8(10) . . ?
O3 C15 C4 116.1(10) . . ?
O2 Cu1 O3 87.8(3) 4_655 6_666 ?
O2 Cu1 O1 89.5(3) 4_655 . ?
O3 Cu1 O1 165.2(3) 6_666 . ?
O2 Cu1 O4 167.6(3) 4_655 7_665 ?
O3 Cu1 O4 90.1(3) 6_666 7_665 ?
O1 Cu1 O4 89.4(3) . 7_665 ?
O2 Cu1 N2 97.0(3) 4_655 8_565 ?
O3 Cu1 N2 98.5(3) 6_666 8_565 ?
O1 Cu1 N2 96.2(3) . 8_565 ?
O4 Cu1 N2 95.3(3) 7_665 8_565 ?
O2 Cu1 Cu1 82.8(2) 4_655 4_655 ?
O3 Cu1 Cu1 81.4(2) 6_666 4_655 ?
O1 Cu1 Cu1 83.9(2) . 4_655 ?
O4 Cu1 Cu1 84.9(2) 7_665 4_655 ?
N2 Cu1 Cu1 179.8(2) 8_565 4_655 ?
C8 N1 C11 107.7(9) . . ?
C8 N1 C6 127.3(10) . . ?
C11 N1 C6 125.0(10) . . ?
C8 N2 C10 106.2(9) . . ?
C8 N2 Cu1 129.9(7) . 8_566 ?
C10 N2 Cu1 123.7(7) . 8_566 ?
C1 O1 Cu1 122.0(6) . . ?
C1 O2 Cu1 124.1(7) . 4_655 ?
C15 O3 Cu1 125.2(7) . 6_556 ?
C15 O4 Cu1 120.1(7) . 7_655 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C7 -153.6(11) . . . . ?
O2 C1 C2 C7 25.0(16) . . . . ?
O1 C1 C2 C3 24.4(16) . . . . ?
O2 C1 C2 C3 -157.0(10) . . . . ?
C7 C2 C3 C4 -1.5(17) . . . . ?
C1 C2 C3 C4 -179.5(11) . . . . ?
C2 C3 C4 C5 0.4(18) . . . . ?
C2 C3 C4 C15 -179.5(10) . . . . ?
C3 C4 C5 C6 -1.2(19) . . . . ?
C15 C4 C5 C6 178.7(11) . . . . ?
C4 C5 C6 C7 3.2(18) . . . . ?
C4 C5 C6 N1 -178.5(11) . . . . ?
C5 C6 C7 C2 -4.5(19) . . . . ?
N1 C6 C7 C2 177.3(11) . . . . ?
C3 C2 C7 C6 3.5(18) . . . . ?
C1 C2 C7 C6 -178.5(11) . . . . ?
N2 C10 C11 N1 2.7(14) . . . . ?
C3 C4 C15 O4 27.5(16) . . . . ?
C5 C4 C15 O4 -152.4(11) . . . . ?
C3 C4 C15 O3 -153.9(11) . . . . ?
C5 C4 C15 O3 26.2(15) . . . . ?
N2 C8 N1 C11 1.9(13) . . . . ?
C9 C8 N1 C11 -179.1(12) . . . . ?
N2 C8 N1 C6 178.8(10) . . . . ?
C9 C8 N1 C6 -2.2(19) . . . . ?
C10 C11 N1 C8 -2.8(13) . . . . ?
C10 C11 N1 C6 -179.7(10) . . . . ?
C5 C6 N1 C8 131.1(13) . . . . ?
C7 C6 N1 C8 -50.6(17) . . . . ?
C5 C6 N1 C11 -52.6(17) . . . . ?
C7 C6 N1 C11 125.7(13) . . . . ?
N1 C8 N2 C10 -0.3(14) . . . . ?
C9 C8 N2 C10 -179.2(12) . . . . ?
N1 C8 N2 Cu1 -175.1(7) . . . 8_566 ?
C9 C8 N2 Cu1 5.9(18) . . . 8_566 ?
C11 C10 N2 C8 -1.6(15) . . . . ?
C11 C10 N2 Cu1 173.7(8) . . . 8_566 ?
O2 C1 O1 Cu1 -0.3(16) . . . . ?
C2 C1 O1 Cu1 178.1(7) . . . . ?
O1 C1 O2 Cu1 3.1(16) . . . 4_655 ?
C2 C1 O2 Cu1 -175.3(7) . . . 4_655 ?
O4 C15 O3 Cu1 2.6(16) . . . 6_556 ?
C4 C15 O3 Cu1 -175.7(7) . . . 6_556 ?
O3 C15 O4 Cu1 -6.9(16) . . . 7_655 ?
C4 C15 O4 Cu1 171.5(7) . . . 7_655 ?

_refine_diff_density_max         0.657
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.157


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 0.010 0.278 0.738 1852 609 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


_shelxl_version_number           2013-2



