# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1879250'
_audit_update_record             
;
2018-12-11 deposited with the CCDC.
2018-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Cu1 N8 O6'
_chemical_formula_sum            'C12 H12 Cu1 N8 O6'
_chemical_formula_weight         427.85

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.8023(3)
_cell_length_b                   7.2850(4)
_cell_length_c                   9.2846(5)
_cell_angle_alpha                93.815(4)
_cell_angle_beta                 111.477(5)
_cell_angle_gamma                112.513(5)
_cell_volume                     383.91(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    173.00(10)
_cell_measurement_reflns_used    5258
_cell_measurement_theta_min      2.4080
_cell_measurement_theta_max      28.0650

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_F_000             217
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.177
_exptl_absorpt_coefficient_mu    1.479
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.374
_exptl_absorpt_correction_T_max  0.814
_oxdiff_exptl_absorpt_empirical_full_min 0.682
_oxdiff_exptl_absorpt_empirical_full_max 1.596
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0965
_diffrn_reflns_number            6378
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.429
_diffrn_reflns_theta_max         28.148
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1737
_reflns_number_gt                1723
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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)+(0.0235P)²+0.2767P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.059(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1737
_refine_ls_number_parameters     125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0203
_refine_ls_wR_factor_ref         0.0543
_refine_ls_wR_factor_gt          0.0542
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 0.5000 0.5000 0.00888(10) Uani 1 2 d S . P . .
N3 N 0.7029(2) 0.49680(17) 0.50079(14) 0.0095(2) Uani 1 1 d . . . . .
O1 O 0.81445(19) 0.14988(16) 0.36098(13) 0.0176(2) Uani 1 1 d . . . . .
N1 N 0.9199(2) 0.58285(18) 0.28409(14) 0.0114(2) Uani 1 1 d . . . . .
O2 O 0.4621(2) -0.0158(2) 0.17181(16) 0.0319(3) Uani 1 1 d . . . . .
O3 O 0.5837(3) -0.1506(2) 0.36468(18) 0.0406(4) Uani 1 1 d . . . . .
N2 N 0.8269(2) 0.7037(2) -0.00380(16) 0.0196(3) Uani 1 1 d . . . . .
N4 N 0.6164(2) -0.00780(19) 0.29876(16) 0.0163(3) Uani 1 1 d . . . . .
C6 C 0.7086(2) 0.6101(2) 0.62282(17) 0.0112(3) Uani 1 1 d . . . . .
H6 H 0.8517 0.6882 0.7101 0.013 Uiso 1 1 calc R U . . .
C5 C 0.4939(2) 0.3862(2) 0.37763(16) 0.0111(3) Uani 1 1 d . . . . .
H5 H 0.4842 0.3056 0.2910 0.013 Uiso 1 1 calc R U . . .
C1 C 0.8023(3) 0.4455(2) 0.14281(17) 0.0142(3) Uani 1 1 d . . . . .
H1 H 0.7495 0.3067 0.1401 0.017 Uiso 1 1 calc R U . . .
C2 C 0.7583(3) 0.5075(2) 0.00095(18) 0.0168(3) Uani 1 1 d . . . . .
H2 H 0.6779 0.4083 -0.0946 0.020 Uiso 1 1 calc R U . . .
C4 C 0.9875(3) 0.7805(2) 0.28063(18) 0.0191(3) Uani 1 1 d . . . . .
H4 H 1.0672 0.8804 0.3757 0.023 Uiso 1 1 calc R U . . .
C3 C 0.9397(3) 0.8377(2) 0.13652(19) 0.0238(4) Uani 1 1 d . . . . .
H3 H 0.9891 0.9762 0.1384 0.029 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 2.0150(11) 2_766 ?
Cu1 N3 2.0150(11) . ?
Cu1 N1 2.0719(12) . ?
Cu1 N1 2.0719(12) 2_766 ?
Cu1 O1 2.3809(11) . ?
Cu1 O1 2.3809(11) 2_766 ?
N3 C6 1.3359(18) . ?
N3 C5 1.3370(18) . ?
O1 N4 1.2746(16) . ?
N1 C4 1.3401(19) . ?
N1 C1 1.3437(19) . ?
O2 N4 1.2383(18) . ?
O3 N4 1.2300(18) . ?
N2 C3 1.328(2) . ?
N2 C2 1.333(2) . ?
C6 C5 1.3866(19) 2_666 ?
C6 H6 0.9300 . ?
C5 C6 1.3866(19) 2_666 ?
C5 H5 0.9300 . ?
C1 C2 1.386(2) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C4 C3 1.389(2) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N3 180.0 2_766 . ?
N3 Cu1 N1 90.68(5) 2_766 . ?
N3 Cu1 N1 89.32(5) . . ?
N3 Cu1 N1 89.33(5) 2_766 2_766 ?
N3 Cu1 N1 90.68(5) . 2_766 ?
N1 Cu1 N1 180.0 . 2_766 ?
N3 Cu1 O1 85.97(4) 2_766 . ?
N3 Cu1 O1 94.03(4) . . ?
N1 Cu1 O1 89.73(4) . . ?
N1 Cu1 O1 90.27(4) 2_766 . ?
N3 Cu1 O1 94.03(4) 2_766 2_766 ?
N3 Cu1 O1 85.97(4) . 2_766 ?
N1 Cu1 O1 90.27(4) . 2_766 ?
N1 Cu1 O1 89.73(4) 2_766 2_766 ?
O1 Cu1 O1 180.00(6) . 2_766 ?
C6 N3 C5 117.51(12) . . ?
C6 N3 Cu1 121.06(9) . . ?
C5 N3 Cu1 121.40(9) . . ?
N4 O1 Cu1 142.42(9) . . ?
C4 N1 C1 116.87(12) . . ?
C4 N1 Cu1 120.32(10) . . ?
C1 N1 Cu1 122.81(10) . . ?
C3 N2 C2 115.80(14) . . ?
O3 N4 O2 121.24(14) . . ?
O3 N4 O1 119.36(14) . . ?
O2 N4 O1 119.40(13) . . ?
N3 C6 C5 121.52(13) . 2_666 ?
N3 C6 H6 119.2 . . ?
C5 C6 H6 119.2 2_666 . ?
N3 C5 C6 120.97(13) . 2_666 ?
N3 C5 H5 119.5 . . ?
C6 C5 H5 119.5 2_666 . ?
N1 C1 C2 121.08(13) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
N2 C2 C1 122.53(14) . . ?
N2 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
N1 C4 C3 120.68(14) . . ?
N1 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
N2 C3 C4 123.02(15) . . ?
N2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-4

