# Electronic Supplementary Material (ESI) for RSC Advances.
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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_compound1

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            coppercitrate
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H14 Cu N6 O8'
_chemical_formula_sum            'C8 H14 Cu N6 O8'
_chemical_formula_weight         385.79

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   11.6890(3)
_cell_length_b                   14.7288(4)
_cell_length_c                   17.9191(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3085.04(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       platelike
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_F_000             1576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.467
_shelx_estimated_absorpt_T_min   0.758
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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            19348
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.865
_diffrn_reflns_theta_max         30.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4657
_reflns_number_gt                3514
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0798P)²+0.7863P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4657
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 -0.00505(2) -0.02161(2) 0.57733(2) 0.02579(10) Uani 1 1 d . . . . .
O1 O -0.12510(12) -0.04881(13) 0.64611(8) 0.0403(4) Uani 1 1 d . . . . .
O2 O -0.10894(12) 0.01622(8) 0.49964(6) 0.0234(3) Uani 1 1 d . . . . .
O3 O 0.10068(13) 0.00114(14) 0.65799(8) 0.0415(4) Uani 1 1 d . . . . .
O4 O -0.24260(15) -0.18830(10) 0.44199(8) 0.0386(4) Uani 1 1 d . . . . .
O5 O -0.28563(13) -0.12024(12) 0.67142(8) 0.0430(4) Uani 1 1 d . . . . .
O6 O 0.25798(14) 0.05877(15) 0.70511(8) 0.0493(5) Uani 1 1 d . . . . .
O7 O -0.08027(14) -0.16448(10) 0.50466(9) 0.0417(4) Uani 1 1 d . . . . .
O8 O 0.81260(17) 0.19285(12) 0.55006(10) 0.0473(4) Uani 1 1 d G . . . .
H8A H 0.7915 0.2246 0.5129 0.071 Uiso 1 1 d G U . . .
H8B H 0.8426 0.1437 0.5347 0.071 Uiso 1 1 d G U . . .
C1 C -0.20700(14) -0.03849(12) 0.48822(10) 0.0221(3) Uani 1 1 d . . . . .
C6 C 0.27001(17) 0.00170(16) 0.58060(10) 0.0297(4) Uani 1 1 d . . . . .
C5 C 0.20727(17) 0.02247(15) 0.65261(11) 0.0317(4) Uani 1 1 d . . . . .
C4 C -0.17285(17) -0.13897(13) 0.47644(11) 0.0279(4) Uani 1 1 d . . . . .
C2 C -0.28335(17) -0.03465(14) 0.55777(11) 0.0283(4) Uani 1 1 d . . . . .
C3 C -0.22807(16) -0.07173(14) 0.62973(10) 0.0293(4) Uani 1 1 d . . . . .
N4 N 0.51255(18) 0.21120(17) 0.37870(12) 0.0488(5) Uani 1 1 d . . . . .
H4A H 0.4406 0.2005 0.3835 0.059 Uiso 1 1 calc R U . . .
H4B H 0.5478 0.2429 0.4118 0.059 Uiso 1 1 calc R U . . .
C8 C 0.56896(19) 0.17901(15) 0.32042(11) 0.0332(4) Uani 1 1 d . . . . .
N5 N 0.68031(16) 0.19372(14) 0.31381(11) 0.0409(4) Uani 1 1 d . . . . .
H5A H 0.7172 0.1716 0.2765 0.049 Uiso 1 1 calc R U . . .
H5B H 0.7157 0.2254 0.3469 0.049 Uiso 1 1 calc R U . . .
N6 N 0.51507(17) 0.13074(17) 0.26995(12) 0.0486(6) Uani 1 1 d . . . . .
H6A H 0.4431 0.1200 0.2748 0.058 Uiso 1 1 calc R U . . .
H6B H 0.5517 0.1098 0.2321 0.058 Uiso 1 1 calc R U . . .
N3 N 0.49355(17) 0.18794(17) 0.60653(14) 0.0481(5) Uani 1 1 d . . . . .
H3A H 0.4208 0.1815 0.6017 0.058 Uiso 1 1 calc R U . . .
H3B H 0.5316 0.2184 0.5740 0.058 Uiso 1 1 calc R U . . .
C12 C 0.54718(19) 0.15079(15) 0.66440(12) 0.0348(4) Uani 1 1 d . . . . .
N2 N 0.65930(17) 0.16029(15) 0.67184(11) 0.0441(5) Uani 1 1 d . . . . .
H2A H 0.6939 0.1360 0.7092 0.053 Uiso 1 1 calc R U . . .
H2B H 0.6975 0.1907 0.6393 0.053 Uiso 1 1 calc R U . . .
N1 N 0.49060(16) 0.10405(19) 0.71470(12) 0.0471(5) Uani 1 1 d . . . . .
H1A H 0.5264 0.0802 0.7518 0.056 Uiso 1 1 calc R U . . .
H1B H 0.4178 0.0973 0.7106 0.056 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 1.9101(14) . ?
Cu1 O2 1.9195(13) 5_556 ?
Cu1 O2 1.9296(13) . ?
Cu1 O3 1.9310(15) . ?
Cu1 Cu1 2.8460(5) 5_556 ?
O1 C3 1.284(2) . ?
O2 C1 1.416(2) . ?
O2 Cu1 1.9194(13) 5_556 ?
O3 C5 1.289(2) . ?
O4 C4 1.254(2) . ?
O5 C3 1.233(2) . ?
O6 C5 1.234(3) . ?
O7 C4 1.252(2) . ?
C1 C2 1.534(3) . ?
C1 C6 1.535(3) 5_556 ?
C1 C4 1.547(3) . ?
C6 C5 1.515(3) . ?
C6 C1 1.535(3) 5_556 ?
C2 C3 1.542(3) . ?
N4 C8 1.323(3) . ?
C8 N6 1.311(3) . ?
C8 N5 1.325(3) . ?
N3 C12 1.330(3) . ?
C12 N1 1.313(3) . ?
C12 N2 1.325(3) . ?

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 O2 169.21(7) . 5_556 ?
O1 Cu1 O2 93.65(6) . . ?
O2 Cu1 O2 84.64(6) 5_556 . ?
O1 Cu1 O3 91.36(6) . . ?
O2 Cu1 O3 94.96(6) 5_556 . ?
O2 Cu1 O3 153.22(7) . . ?
O1 Cu1 Cu1 134.88(5) . 5_556 ?
O2 Cu1 Cu1 42.46(4) 5_556 5_556 ?
O2 Cu1 Cu1 42.18(4) . 5_556 ?
O3 Cu1 Cu1 131.57(5) . 5_556 ?
C3 O1 Cu1 126.61(13) . . ?
C1 O2 Cu1 118.79(10) . 5_556 ?
C1 O2 Cu1 116.71(10) . . ?
Cu1 O2 Cu1 95.36(6) 5_556 . ?
C5 O3 Cu1 127.24(14) . . ?
O2 C1 C2 109.43(14) . . ?
O2 C1 C6 107.67(14) . 5_556 ?
C2 C1 C6 111.13(15) . 5_556 ?
O2 C1 C4 110.80(14) . . ?
C2 C1 C4 107.23(15) . . ?
C6 C1 C4 110.60(16) 5_556 . ?
C5 C6 C1 112.37(16) . 5_556 ?
O6 C5 O3 120.9(2) . . ?
O6 C5 C6 120.28(18) . . ?
O3 C5 C6 118.84(18) . . ?
O7 C4 O4 125.92(19) . . ?
O7 C4 C1 117.06(17) . . ?
O4 C4 C1 116.96(17) . . ?
C1 C2 C3 114.99(16) . . ?
O5 C3 O1 121.68(18) . . ?
O5 C3 C2 118.88(18) . . ?
O1 C3 C2 119.39(17) . . ?
N6 C8 N4 119.9(2) . . ?
N6 C8 N5 119.9(2) . . ?
N4 C8 N5 120.1(2) . . ?
N1 C12 N2 119.0(2) . . ?
N1 C12 N3 120.9(2) . . ?
N2 C12 N3 120.1(2) . . ?

_refine_diff_density_max         0.843
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.081

_shelxl_version_number           2013-4



#####EOF#####

_database_code_depnum_ccdc_archive 'CCDC 978079'
