# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014


data_xb6675

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H3 Cu N5 O6'
_chemical_formula_weight         316.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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

_cell_length_a                   6.747(2)
_cell_length_b                   9.047(3)
_cell_length_c                   16.973(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1036.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    955
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      22.14

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.030
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             628
_exptl_absorpt_coefficient_mu    2.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.604
_exptl_absorpt_correction_T_max  0.725
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5301
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_av_sigmaI/netI    0.0987
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         26.12
_reflns_number_total             2041
_reflns_number_gt                1497
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0593P)²+0.0811P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_number_reflns         2041
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1408
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.5260(6) 0.7534(5) 0.6095(3) 0.0411(12) Uani 1 1 d . . .
Cu1 Cu 0.10932(8) 0.73309(8) 0.50029(5) 0.0345(3) Uani 1 1 d . . .
N2 N 0.3263(8) 0.9362(8) 0.4164(4) 0.0432(16) Uani 1 1 d . . .
N3 N 0.3014(10) 1.0161(9) 0.3650(4) 0.062(2) Uani 1 1 d . . .
N1 N 0.3489(8) 0.8504(7) 0.4726(3) 0.0401(15) Uani 1 1 d . . .
O1 O 0.2149(7) 0.6680(6) 0.6007(2) 0.0436(13) Uani 1 1 d . . .
O4 O 0.0682(8) 0.4695(6) 0.9477(3) 0.0588(16) Uani 1 1 d . . .
O3 O -0.0971(8) 0.4741(8) 0.8387(3) 0.0720(19) Uani 1 1 d . . .
O5 O 0.8249(10) 0.8153(9) 0.8664(4) 0.087(2) Uani 1 1 d . . .
O6 O 0.6935(9) 0.7110(8) 0.9674(3) 0.0752(19) Uani 1 1 d . . .
C7 C 0.5292(10) 0.7214(9) 0.7700(4) 0.0385(17) Uani 1 1 d . . .
H1 H 0.6375 0.7681 0.7470 0.046 Uiso 1 1 calc R . .
N5 N 0.0514(9) 0.5016(7) 0.8787(4) 0.0471(16) Uani 1 1 d . . .
C3 C 0.2088(10) 0.6052(8) 0.7607(3) 0.0362(16) Uani 1 1 d . . .
H2 H 0.0998 0.5746 0.7314 0.043 Uiso 1 1 calc R . .
C4 C 0.2165(10) 0.5809(8) 0.8400(4) 0.0359(16) Uani 1 1 d . . .
C6 C 0.5246(9) 0.6948(8) 0.8497(4) 0.0368(17) Uani 1 1 d . . .
C5 C 0.3764(10) 0.6228(8) 0.8864(4) 0.0392(17) Uani 1 1 d . . .
H3 H 0.3807 0.6023 0.9401 0.047 Uiso 1 1 calc R . .
C2 C 0.3680(8) 0.6769(8) 0.7246(3) 0.0333(15) Uani 1 1 d . . .
C1 C 0.3675(9) 0.7006(9) 0.6379(4) 0.0362(16) Uani 1 1 d . . .
N4 N 0.6939(10) 0.7459(7) 0.8986(4) 0.0516(18) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.023(2) 0.065(4) 0.035(3) 0.006(2) 0.0034(19) 0.001(2)
Cu1 0.0167(3) 0.0544(5) 0.0324(4) 0.0033(5) -0.0004(4) 0.0000(3)
N2 0.019(3) 0.057(4) 0.054(4) 0.001(4) 0.002(3) -0.001(3)
N3 0.040(4) 0.070(5) 0.074(5) 0.030(5) -0.012(4) -0.004(4)
N1 0.022(3) 0.056(4) 0.042(3) 0.015(3) 0.001(2) -0.001(3)
O1 0.030(3) 0.065(4) 0.036(2) 0.014(3) -0.006(2) -0.009(2)
O4 0.057(4) 0.073(4) 0.046(3) 0.016(3) 0.007(3) -0.008(3)
O3 0.046(3) 0.100(5) 0.070(4) 0.012(4) -0.005(3) -0.032(4)
O5 0.070(4) 0.110(6) 0.082(4) 0.028(5) -0.030(4) -0.050(4)
O6 0.069(4) 0.113(5) 0.044(3) -0.002(4) -0.022(3) -0.015(4)
C7 0.031(4) 0.051(5) 0.034(4) 0.007(3) 0.004(3) -0.001(3)
N5 0.040(4) 0.058(4) 0.043(4) 0.007(4) 0.007(3) -0.001(3)
C3 0.021(3) 0.053(5) 0.035(4) 0.006(3) -0.008(3) -0.005(3)
C4 0.029(3) 0.045(4) 0.033(4) 0.003(3) 0.007(3) -0.001(3)
C6 0.025(3) 0.043(4) 0.042(4) -0.006(3) -0.001(3) -0.007(3)
C5 0.037(4) 0.044(4) 0.037(4) 0.004(3) -0.004(3) 0.005(4)
C2 0.020(3) 0.050(4) 0.030(3) 0.003(3) 0.003(3) 0.002(3)
C1 0.024(3) 0.047(4) 0.038(4) -0.001(3) -0.003(3) 0.000(3)
N4 0.039(3) 0.065(5) 0.050(4) 0.006(3) -0.010(3) -0.008(3)

_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
O2 C1 1.266(8) . ?
O2 Cu1 1.950(4) 4_566 ?
Cu1 O1 1.939(4) . ?
Cu1 O2 1.950(4) 4_466 ?
Cu1 N1 1.967(6) 4_466 ?
Cu1 N1 1.990(5) . ?
N2 N3 1.145(8) . ?
N2 N1 1.239(8) . ?
N1 Cu1 1.967(5) 4_566 ?
O1 C1 1.243(7) . ?
O4 N5 1.212(7) . ?
O3 N5 1.236(7) . ?
O5 N4 1.214(8) . ?
O6 N4 1.210(7) . ?
C7 C6 1.374(9) . ?
C7 C2 1.394(9) . ?
C7 H1 0.9300 . ?
N5 C4 1.479(8) . ?
C3 C4 1.363(8) . ?
C3 C2 1.397(9) . ?
C3 H2 0.9300 . ?
C4 C5 1.389(9) . ?
C6 C5 1.347(9) . ?
C6 N4 1.485(9) . ?
C5 H3 0.9300 . ?
C2 C1 1.487(8) . ?

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
C1 O2 Cu1 129.1(4) . 4_566 ?
O1 Cu1 O2 164.8(2) . 4_466 ?
O1 Cu1 N1 90.3(2) . 4_466 ?
O2 Cu1 N1 89.4(2) 4_466 4_466 ?
O1 Cu1 N1 94.1(2) . . ?
O2 Cu1 N1 88.6(2) 4_466 . ?
N1 Cu1 N1 170.26(14) 4_466 . ?
N3 N2 N1 178.6(7) . . ?
N2 N1 Cu1 122.1(4) . 4_566 ?
N2 N1 Cu1 114.6(5) . . ?
Cu1 N1 Cu1 117.7(3) 4_566 . ?
C1 O1 Cu1 132.7(5) . . ?
C6 C7 C2 118.5(6) . . ?
C6 C7 H1 120.8 . . ?
C2 C7 H1 120.8 . . ?
O4 N5 O3 123.9(6) . . ?
O4 N5 C4 118.4(6) . . ?
O3 N5 C4 117.6(6) . . ?
C4 C3 C2 118.6(6) . . ?
C4 C3 H2 120.7 . . ?
C2 C3 H2 120.7 . . ?
C3 C4 C5 123.0(6) . . ?
C3 C4 N5 119.2(6) . . ?
C5 C4 N5 117.7(5) . . ?
C5 C6 C7 123.9(6) . . ?
C5 C6 N4 117.6(6) . . ?
C7 C6 N4 118.6(6) . . ?
C6 C5 C4 116.5(6) . . ?
C6 C5 H3 121.7 . . ?
C4 C5 H3 121.7 . . ?
C7 C2 C3 119.4(6) . . ?
C7 C2 C1 120.5(6) . . ?
C3 C2 C1 120.0(6) . . ?
O1 C1 O2 126.6(6) . . ?
O1 C1 C2 118.0(6) . . ?
O2 C1 C2 115.4(6) . . ?
O6 N4 O5 124.8(7) . . ?
O6 N4 C6 117.1(7) . . ?
O5 N4 C6 118.0(6) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.12
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.883
_refine_diff_density_rms         0.140
_database_code_depnum_ccdc_archive 'CCDC 970127'
