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


data_x

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H6 Cu N4 O4'
_chemical_formula_weight         285.71

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           ?
_symmetry_space_group_name_H-M   p-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.785(5)
_cell_length_b                   7.594(6)
_cell_length_c                   10.591(8)
_cell_angle_alpha                70.714(15)
_cell_angle_beta                 77.107(14)
_cell_angle_gamma                88.869(14)
_cell_volume                     501.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3524
_cell_measurement_theta_min      1.96
_cell_measurement_theta_max      25.10

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.893
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             286
_exptl_absorpt_coefficient_mu    2.188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7973
_exptl_absorpt_correction_T_max  0.9019
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1736
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1331
_diffrn_reflns_limit_h_min       -7
_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       11
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1736
_reflns_number_gt                828
_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)+(0.0000P)²+8.9000P] 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     SHELXL
_refine_ls_extinction_coef       0.061(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1736
_refine_ls_number_parameters     217
_refine_ls_number_restraints     492
_refine_ls_R_factor_all          0.1716
_refine_ls_R_factor_gt           0.0858
_refine_ls_wR_factor_ref         0.2360
_refine_ls_wR_factor_gt          0.1803
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      0.928
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 1.0000 0.5000 0.0376(8) Uani 1 2 d S . .
Cu2 Cu 0.0000 1.0000 0.5000 0.0636(11) Uani 1 2 d S . .
O1 O 0.4337(15) 0.7916(15) 0.4501(12) 0.069(3) Uani 1 1 d . . .
O2 O 0.1101(13) 0.7907(16) 0.4477(12) 0.069(4) Uani 1 1 d . . .
N1 N 0.2242(16) 1.007(2) 0.5922(14) 0.066(4) Uani 1 1 d . . .
N2 N 0.1832(17) 1.038(2) 0.6977(16) 0.083(5) Uani 1 1 d . . .
N3 N 0.147(2) 1.066(3) 0.802(2) 0.131(8) Uani 1 1 d . . .
C1 C 0.272(2) 0.7279(18) 0.4329(13) 0.042(3) Uani 1 1 d . A .
C2 C 0.308(2) 0.5592(19) 0.3837(15) 0.057(4) Uani 1 1 d D . .
H2A H 0.4074 0.4834 0.4265 0.068 Uiso 0.498(10) 1 calc PR A 1
H2B H 0.1828 0.4829 0.4104 0.068 Uiso 0.498(10) 1 calc PR A 1
H2C H 0.1789 0.5073 0.3829 0.068 Uiso 0.502(10) 1 calc PR A 2
H2D H 0.3683 0.4638 0.4478 0.068 Uiso 0.502(10) 1 calc PR A 2
C3 C 0.382(3) 0.624(3) 0.2308(10) 0.051(4) Uani 0.498(10) 1 d PGDU A 1
C4 C 0.584(3) 0.591(3) 0.1875(15) 0.050(4) Uani 0.498(10) 1 d PGU A 1
H4A H 0.6581 0.5302 0.2518 0.060 Uiso 0.498(10) 1 calc PR A 1
C5 C 0.676(2) 0.649(3) 0.0480(17) 0.049(4) Uani 0.498(10) 1 d PGU A 1
H5A H 0.8107 0.6277 0.0190 0.059 Uiso 0.498(10) 1 calc PR A 1
C6 C 0.565(3) 0.740(3) -0.0480(10) 0.046(4) Uani 0.498(10) 1 d PGDU A 1
C7 C 0.363(3) 0.773(3) -0.0047(14) 0.055(4) Uani 0.498(10) 1 d PGU A 1
H7A H 0.2889 0.8337 -0.0690 0.066 Uiso 0.498(10) 1 calc PR A 1
C8 C 0.271(2) 0.714(3) 0.1348(16) 0.052(4) Uani 0.498(10) 1 d PGU A 1
H8A H 0.1362 0.7362 0.1638 0.063 Uiso 0.498(10) 1 calc PR A 1
N4 N 0.651(3) 0.793(3) -0.185(2) 0.047(5) Uani 0.498(10) 1 d PDU A 1
O3 O 0.823(3) 0.767(3) -0.211(3) 0.041(6) Uani 0.498(10) 1 d PDU A 1
O4 O 0.541(3) 0.850(3) -0.258(2) 0.075(6) Uani 0.498(10) 1 d PDU A 1
C3B C 0.448(3) 0.611(3) 0.2380(11) 0.047(4) Uani 0.502(10) 1 d PGDU A 2
C4B C 0.630(3) 0.523(3) 0.2224(13) 0.050(4) Uani 0.502(10) 1 d PGU A 2
H4B H 0.6675 0.4417 0.2991 0.059 Uiso 0.502(10) 1 calc PR A 2
C5B C 0.754(2) 0.558(3) 0.0923(17) 0.047(4) Uani 0.502(10) 1 d PGU A 2
H5B H 0.8749 0.4988 0.0819 0.056 Uiso 0.502(10) 1 calc PR A 2
C6B C 0.697(2) 0.680(3) -0.0223(12) 0.047(4) Uani 0.502(10) 1 d PGDU A 2
C7B C 0.516(3) 0.768(2) -0.0067(13) 0.046(4) Uani 0.502(10) 1 d PGU A 2
H7B H 0.4780 0.8494 -0.0833 0.055 Uiso 0.502(10) 1 calc PR A 2
C8B C 0.392(2) 0.733(3) 0.1235(17) 0.054(4) Uani 0.502(10) 1 d PGU A 2
H8B H 0.2705 0.7922 0.1339 0.065 Uiso 0.502(10) 1 calc PR A 2
N4B N 0.826(5) 0.713(5) -0.149(2) 0.060(7) Uani 0.502(10) 1 d PDU A 2
O3B O 0.976(3) 0.642(3) -0.183(2) 0.080(6) Uani 0.502(10) 1 d PDU A 2
O4B O 0.762(4) 0.826(3) -0.265(2) 0.058(6) Uani 0.502(10) 1 d PDU A 2

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
Cu1 0.0239(13) 0.0471(17) 0.0476(16) -0.0237(13) -0.0082(11) 0.0037(11)
Cu2 0.0232(15) 0.096(3) 0.105(2) -0.079(2) -0.0121(14) 0.0065(14)
O1 0.052(7) 0.060(7) 0.119(10) -0.054(7) -0.032(6) 0.009(5)
O2 0.016(5) 0.109(10) 0.120(10) -0.083(8) -0.021(5) 0.016(5)
N1 0.023(6) 0.131(13) 0.080(9) -0.086(10) -0.010(6) 0.021(7)
N2 0.024(7) 0.148(15) 0.099(12) -0.088(12) 0.011(7) -0.015(8)
N3 0.079(12) 0.21(2) 0.140(16) -0.143(17) 0.039(11) -0.049(13)
C1 0.054(9) 0.028(8) 0.040(8) -0.005(6) -0.014(7) -0.004(7)
C2 0.081(11) 0.036(9) 0.063(10) -0.029(8) -0.012(9) -0.023(8)
C3 0.068(8) 0.049(7) 0.046(7) -0.017(6) -0.028(7) -0.011(7)
C4 0.064(8) 0.047(8) 0.044(7) -0.016(6) -0.025(7) -0.006(7)
C5 0.067(8) 0.045(7) 0.045(7) -0.020(6) -0.024(7) -0.008(7)
C6 0.064(8) 0.044(7) 0.043(7) -0.022(6) -0.025(7) -0.008(7)
C7 0.071(8) 0.051(7) 0.047(7) -0.015(6) -0.024(7) -0.010(7)
C8 0.069(8) 0.049(7) 0.048(7) -0.018(6) -0.025(7) -0.010(7)
N4 0.068(12) 0.032(11) 0.052(13) -0.022(10) -0.023(10) 0.008(10)
O3 0.044(10) 0.042(14) 0.038(14) -0.009(11) -0.020(10) 0.009(9)
O4 0.092(13) 0.060(12) 0.054(12) -0.003(10) -0.005(10) 0.018(11)
C3B 0.065(8) 0.046(7) 0.045(7) -0.020(6) -0.031(7) -0.010(7)
C4B 0.066(8) 0.048(8) 0.044(7) -0.018(6) -0.024(7) -0.006(7)
C5B 0.065(8) 0.046(7) 0.043(7) -0.023(6) -0.027(7) -0.012(7)
C6B 0.067(8) 0.043(7) 0.043(7) -0.021(6) -0.024(7) -0.007(7)
C7B 0.062(8) 0.045(7) 0.041(7) -0.019(6) -0.026(7) -0.009(7)
C8B 0.070(8) 0.050(7) 0.049(7) -0.017(6) -0.025(7) -0.010(7)
N4B 0.066(12) 0.045(13) 0.066(15) -0.010(12) -0.025(12) 0.000(11)
O3B 0.072(12) 0.085(13) 0.063(12) -0.012(11) 0.006(10) 0.007(11)
O4B 0.076(13) 0.063(13) 0.034(12) -0.019(11) -0.008(10) 0.006(11)

_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 1.917(10) 2_676 ?
Cu1 O1 1.917(10) . ?
Cu1 N1 1.917(11) . ?
Cu1 N1 1.917(11) 2_676 ?
Cu2 O2 1.934(10) 2_576 ?
Cu2 O2 1.934(10) . ?
Cu2 N1 1.993(11) . ?
Cu2 N1 1.993(11) 2_576 ?
O1 C1 1.281(16) . ?
O2 C1 1.187(16) . ?
N1 N2 1.189(16) . ?
N2 N3 1.160(18) . ?
C1 C2 1.531(17) . ?
C2 C3 1.495(16) . ?
C2 C3B 1.549(16) . ?
C3 C4 1.3900 . ?
C3 C8 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 N4 1.36(2) . ?
C6 C7 1.3900 . ?
C7 C8 1.3900 . ?
N4 O4 1.166(19) . ?
N4 O3 1.166(19) . ?
C3B C4B 1.3900 . ?
C3B C8B 1.3900 . ?
C4B C5B 1.3900 . ?
C5B C6B 1.3900 . ?
C6B N4B 1.38(2) . ?
C6B C7B 1.3900 . ?
C7B C8B 1.3900 . ?
N4B O3B 1.18(2) . ?
N4B O4B 1.39(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 O1 180.000(2) 2_676 . ?
O1 Cu1 N1 88.5(5) 2_676 . ?
O1 Cu1 N1 91.5(5) . . ?
O1 Cu1 N1 91.5(5) 2_676 2_676 ?
O1 Cu1 N1 88.5(5) . 2_676 ?
N1 Cu1 N1 180.000(1) . 2_676 ?
O2 Cu2 O2 180.000(2) 2_576 . ?
O2 Cu2 N1 88.7(4) 2_576 . ?
O2 Cu2 N1 91.3(4) . . ?
O2 Cu2 N1 91.3(4) 2_576 2_576 ?
O2 Cu2 N1 88.7(4) . 2_576 ?
N1 Cu2 N1 180.000(1) . 2_576 ?
C1 O1 Cu1 134.6(10) . . ?
C1 O2 Cu2 135.3(9) . . ?
N2 N1 Cu1 121.3(10) . . ?
N2 N1 Cu2 117.7(9) . . ?
Cu1 N1 Cu2 120.4(6) . . ?
N3 N2 N1 178(2) . . ?
O2 C1 O1 126.2(13) . . ?
O2 C1 C2 121.3(13) . . ?
O1 C1 C2 112.5(13) . . ?
C3 C2 C1 110.0(14) . . ?
C3 C2 C3B 17.9(11) . . ?
C1 C2 C3B 112.2(13) . . ?
C4 C3 C8 120.0 . . ?
C4 C3 C2 113.6(14) . . ?
C8 C3 C2 126.3(14) . . ?
C5 C4 C3 120.0 . . ?
C4 C5 C6 120.0 . . ?
N4 C6 C7 119.4(15) . . ?
N4 C6 C5 120.6(15) . . ?
C7 C6 C5 120.0 . . ?
C6 C7 C8 120.0 . . ?
C7 C8 C3 120.0 . . ?
O4 N4 O3 130(3) . . ?
O4 N4 C6 115(2) . . ?
O3 N4 C6 114(2) . . ?
C4B C3B C8B 120.0 . . ?
C4B C3B C2 118.3(13) . . ?
C8B C3B C2 121.6(13) . . ?
C5B C4B C3B 120.0 . . ?
C4B C5B C6B 120.0 . . ?
N4B C6B C7B 121.7(18) . . ?
N4B C6B C5B 118.3(18) . . ?
C7B C6B C5B 120.0 . . ?
C6B C7B C8B 120.0 . . ?
C7B C8B C3B 120.0 . . ?
O3B N4B C6B 131(3) . . ?
O3B N4B O4B 110(2) . . ?
C6B N4B O4B 118(2) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.220
_database_code_depnum_ccdc_archive 'CCDC 972616'

data_xb6659

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 Cu N3 O2'
_chemical_formula_weight         254.73

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           ?
_symmetry_space_group_name_H-M   p21/c

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

_cell_length_a                   17.787(3)
_cell_length_b                   6.6764(13)
_cell_length_c                   8.4841(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.003(3)
_cell_angle_gamma                90.00
_cell_volume                     985.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3524
_cell_measurement_theta_min      1.96
_cell_measurement_theta_max      25.10

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    2.197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7973
_exptl_absorpt_correction_T_max  0.9019
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4869
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_sigmaI/netI    0.0877
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.48
_reflns_number_total             1816
_reflns_number_gt                1145
_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)+(0.0840P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1816
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1628
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.009

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
Cu1 Cu 1.01452(5) 0.42131(11) 0.80177(9) 0.0340(3) Uani 1 1 d . . .
C1 C 0.6903(4) 0.7238(13) 0.6447(9) 0.052(2) Uani 1 1 d . . .
H5 H 0.6952 0.8560 0.6799 0.063 Uiso 1 1 calc R . .
C2 C 0.6303(4) 0.6725(15) 0.5118(9) 0.060(2) Uani 1 1 d . . .
H4 H 0.5963 0.7702 0.4617 0.072 Uiso 1 1 calc R . .
C3 C 0.6230(4) 0.4790(16) 0.4580(10) 0.059(2) Uani 1 1 d . . .
C4 C 0.6743(5) 0.3391(14) 0.5369(11) 0.068(3) Uani 1 1 d . . .
H6 H 0.6700 0.2066 0.5023 0.082 Uiso 1 1 calc R . .
C5 C 0.7326(4) 0.3915(12) 0.6678(9) 0.0500(19) Uani 1 1 d . . .
H7 H 0.7664 0.2942 0.7192 0.060 Uiso 1 1 calc R . .
C6 C 0.7401(4) 0.5860(11) 0.7208(8) 0.0382(16) Uani 1 1 d . . .
C7 C 0.5589(5) 0.4156(18) 0.3178(12) 0.099(4) Uani 1 1 d . . .
H2 H 0.5101 0.4316 0.3476 0.149 Uiso 1 1 calc R . .
H1 H 0.5658 0.2777 0.2919 0.149 Uiso 1 1 calc R . .
H3 H 0.5605 0.4975 0.2255 0.149 Uiso 1 1 calc R . .
C8 C 0.8035(4) 0.6458(12) 0.8662(8) 0.0442(18) Uani 1 1 d . . .
H9 H 0.7892 0.7708 0.9105 0.053 Uiso 1 1 calc R . .
H8 H 0.8071 0.5440 0.9491 0.053 Uiso 1 1 calc R . .
C9 C 0.8805(3) 0.6702(10) 0.8228(7) 0.0313(15) Uani 1 1 d . . .
N1 N 1.0781(4) 0.6422(8) 0.5860(7) 0.0430(15) Uani 1 1 d . . .
N2 N 1.1218(4) 0.6336(10) 0.5077(8) 0.064(2) Uani 1 1 d . . .
N3 N 1.0300(3) 0.6553(8) 0.6701(7) 0.0388(14) Uani 1 1 d . . .
O1 O 0.9332(3) 0.5503(6) 0.8900(5) 0.0395(12) Uani 1 1 d . . .
O12 O 0.8898(2) 0.8086(6) 0.7285(5) 0.0361(11) 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
Cu1 0.0438(6) 0.0230(5) 0.0385(5) -0.0002(4) 0.0162(4) 0.0009(4)
C1 0.049(5) 0.056(5) 0.054(5) 0.009(4) 0.016(4) 0.002(4)
C2 0.042(5) 0.082(7) 0.057(5) 0.011(5) 0.008(4) 0.012(4)
C3 0.037(4) 0.092(7) 0.045(5) 0.006(5) 0.004(3) -0.005(5)
C4 0.085(7) 0.057(6) 0.071(6) -0.020(5) 0.036(5) -0.029(5)
C5 0.044(5) 0.047(5) 0.054(5) 0.007(4) 0.000(4) 0.004(4)
C6 0.027(3) 0.051(4) 0.038(4) -0.001(3) 0.008(3) 0.000(3)
C7 0.078(7) 0.142(11) 0.078(7) -0.021(7) 0.012(6) -0.039(7)
C8 0.041(4) 0.046(4) 0.048(4) 0.003(4) 0.015(3) 0.000(3)
C9 0.033(4) 0.029(4) 0.029(3) -0.003(3) 0.000(3) 0.000(3)
N1 0.063(4) 0.023(3) 0.047(3) 0.002(3) 0.020(3) 0.000(3)
N2 0.088(5) 0.051(4) 0.069(4) -0.002(4) 0.054(4) 0.000(4)
N3 0.057(4) 0.022(3) 0.045(3) 0.002(3) 0.028(3) 0.000(3)
O1 0.054(3) 0.030(3) 0.037(3) 0.007(2) 0.017(2) 0.005(2)
O12 0.035(3) 0.035(3) 0.038(2) 0.009(2) 0.0078(19) 0.001(2)

_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 O12 1.926(4) 2_746 ?
Cu1 O1 1.960(4) . ?
Cu1 N3 1.973(5) . ?
Cu1 N3 1.979(5) 2_746 ?
C1 C6 1.345(10) . ?
C1 C2 1.424(10) . ?
C2 C3 1.368(13) . ?
C3 C4 1.378(12) . ?
C3 C7 1.526(11) . ?
C4 C5 1.397(11) . ?
C5 C6 1.372(10) . ?
C6 C8 1.541(9) . ?
C8 C9 1.500(8) . ?
C9 O12 1.256(7) . ?
C9 O1 1.274(7) . ?
N1 N2 1.125(7) . ?
N1 N3 1.225(8) . ?
N3 Cu1 1.979(5) 2_756 ?
O12 Cu1 1.926(4) 2_756 ?

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
O12 Cu1 O1 164.77(19) 2_746 . ?
O12 Cu1 N3 90.1(2) 2_746 . ?
O1 Cu1 N3 94.0(2) . . ?
O12 Cu1 N3 93.0(2) 2_746 2_746 ?
O1 Cu1 N3 90.1(2) . 2_746 ?
N3 Cu1 N3 152.29(9) . 2_746 ?
C6 C1 C2 121.7(8) . . ?
C3 C2 C1 119.7(8) . . ?
C2 C3 C4 118.1(7) . . ?
C2 C3 C7 121.7(9) . . ?
C4 C3 C7 120.2(9) . . ?
C3 C4 C5 121.6(8) . . ?
C6 C5 C4 120.2(7) . . ?
C1 C6 C5 118.7(7) . . ?
C1 C6 C8 120.4(7) . . ?
C5 C6 C8 120.9(6) . . ?
C9 C8 C6 112.6(5) . . ?
O12 C9 O1 124.4(6) . . ?
O12 C9 C8 119.0(6) . . ?
O1 C9 C8 116.6(6) . . ?
N2 N1 N3 178.7(7) . . ?
N1 N3 Cu1 118.0(4) . . ?
N1 N3 Cu1 118.7(4) . 2_756 ?
Cu1 N3 Cu1 122.4(3) . 2_756 ?
C9 O1 Cu1 129.6(4) . . ?
C9 O12 Cu1 127.6(4) . 2_756 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.119
_database_code_depnum_ccdc_archive 'CCDC 972617'

data_xb6929_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 Cu N4 O5'
_chemical_formula_weight         303.72

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'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P21/N

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

_cell_length_a                   13.5498(16)
_cell_length_b                   6.5985(8)
_cell_length_c                   13.6226(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.118(2)
_cell_angle_gamma                90.00
_cell_volume                     1093.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3524
_cell_measurement_theta_min      1.96
_cell_measurement_theta_max      25.10

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_absorpt_coefficient_mu    2.018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7973
_exptl_absorpt_correction_T_max  0.9019
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5269
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         25.14
_reflns_number_total             1937
_reflns_number_gt                1535
_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)+(0.0400P)²+0.0000P] 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_number_reflns         1937
_refine_ls_number_parameters     164
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0795
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.26953(19) 0.3572(3) 0.39932(16) 0.0311(5) Uani 1 1 d . . .
Cu1 Cu 0.25165(3) -0.05722(5) 0.24499(3) 0.02570(15) Uani 1 1 d . . .
O1 O 0.2611(2) 0.0178(3) 0.38544(18) 0.0406(6) Uani 1 1 d . . .
N1 N 0.1617(2) 0.1922(4) 0.1817(2) 0.0290(6) Uani 1 1 d . . .
N2 N 0.1029(2) 0.2052(4) 0.0842(3) 0.0376(7) Uani 1 1 d . . .
C5 C 0.3171(3) 0.3345(5) 0.6249(2) 0.0274(7) Uani 1 1 d . . .
C6 C 0.2540(2) 0.5086(5) 0.6090(2) 0.0261(7) Uani 1 1 d . . .
C7 C 0.2839(3) 0.6679(5) 0.6827(3) 0.0330(8) Uani 1 1 d . . .
H7 H 0.2392 0.7817 0.6686 0.040 Uiso 1 1 calc R . .
C8 C 0.2715(3) 0.1825(5) 0.4351(2) 0.0264(7) Uani 1 1 d . . .
N4 N 0.1490(2) 0.5331(5) 0.5099(2) 0.0365(7) Uani 1 1 d . . .
C10 C 0.4159(3) 0.3317(5) 0.7201(3) 0.0354(8) Uani 1 1 d . . .
H10 H 0.4628 0.2213 0.7334 0.042 Uiso 1 1 calc R . .
O3 O 0.1253(2) 0.7023(4) 0.4711(2) 0.0609(8) Uani 1 1 d . . .
C12 C 0.3808(3) 0.6554(5) 0.7770(3) 0.0381(9) Uani 1 1 d . . .
H132 H 0.4017 0.7600 0.8279 0.046 Uiso 1 1 calc R . .
O4 O 0.0914(2) 0.3852(4) 0.4720(2) 0.0523(7) Uani 1 1 d . . .
C14 C 0.4463(3) 0.4875(6) 0.7952(3) 0.0401(9) Uani 1 1 d . . .
H14 H 0.5118 0.4787 0.8588 0.048 Uiso 1 1 calc R . .
O5 O 0.4076(2) 0.1540(5) 0.2723(2) 0.0620(9) Uani 1 1 d D . .
H5B H 0.4045 0.1857 0.2128 0.093 Uiso 1 1 calc R . .
C16 C 0.2872(3) 0.1533(5) 0.5517(3) 0.0344(8) Uani 1 1 d . . .
H16A H 0.2195 0.0977 0.5485 0.041 Uiso 1 1 calc R . .
H16B H 0.3440 0.0519 0.5859 0.041 Uiso 1 1 calc R . .
N3 N 0.0453(3) 0.2201(5) -0.0060(3) 0.0750(13) Uani 1 1 d . . .
H5A H 0.4615 0.1847 0.3286 0.112 Uiso 1 1 d RD . .

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 0.0519(14) 0.0214(12) 0.0189(11) 0.0011(9) 0.0144(11) -0.0034(10)
Cu1 0.0383(3) 0.0174(2) 0.0193(2) -0.00044(15) 0.01070(18) 0.00155(16)
O1 0.0747(18) 0.0236(13) 0.0235(13) 0.0014(10) 0.0217(13) 0.0080(12)
N1 0.0371(15) 0.0206(15) 0.0213(16) -0.0005(11) 0.0055(13) 0.0008(11)
N2 0.0416(17) 0.0224(15) 0.0372(19) 0.0018(13) 0.0068(15) -0.0015(13)
C5 0.0403(19) 0.0232(17) 0.0199(17) 0.0038(14) 0.0144(15) -0.0002(14)
C6 0.0285(17) 0.0284(18) 0.0173(16) 0.0026(14) 0.0062(14) -0.0004(13)
C7 0.040(2) 0.0254(18) 0.036(2) -0.0019(15) 0.0191(17) 0.0020(15)
C8 0.0322(18) 0.0239(18) 0.0207(17) 0.0026(14) 0.0096(14) 0.0025(14)
N4 0.0379(17) 0.0409(19) 0.0271(16) 0.0027(14) 0.0110(14) 0.0025(15)
C10 0.0366(19) 0.038(2) 0.0302(19) 0.0016(16) 0.0131(16) 0.0065(16)
O3 0.0607(18) 0.0481(19) 0.0516(19) 0.0212(15) 0.0042(15) 0.0103(14)
C12 0.045(2) 0.035(2) 0.033(2) -0.0135(17) 0.0160(18) -0.0116(17)
O4 0.0422(15) 0.0585(17) 0.0406(16) -0.0067(14) 0.0040(13) -0.0116(14)
C14 0.0315(19) 0.050(2) 0.0277(19) -0.0030(17) 0.0031(16) -0.0026(17)
O5 0.0539(17) 0.090(2) 0.0339(16) -0.0045(17) 0.0116(14) -0.0318(16)
C16 0.057(2) 0.0199(17) 0.0254(18) 0.0025(14) 0.0176(17) 0.0030(15)
N3 0.081(3) 0.055(2) 0.036(2) 0.0133(18) -0.023(2) -0.0122(19)

_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 C8 1.247(4) . ?
O2 Cu1 1.942(2) 2 ?
Cu1 O1 1.925(2) . ?
Cu1 O2 1.942(2) 2_545 ?
Cu1 N1 2.003(2) . ?
Cu1 N1 2.019(2) 2_545 ?
Cu1 O5 2.419(3) . ?
O1 C8 1.255(4) . ?
N1 N2 1.214(4) . ?
N1 Cu1 2.019(2) 2 ?
N2 N3 1.133(4) . ?
C5 C6 1.391(4) . ?
C5 C10 1.395(4) . ?
C5 C16 1.495(4) . ?
C6 C7 1.385(4) . ?
C6 N4 1.477(4) . ?
C7 C12 1.377(5) . ?
C8 C16 1.519(4) . ?
N4 O4 1.213(4) . ?
N4 O3 1.216(3) . ?
C10 C14 1.379(5) . ?
C12 C14 1.372(5) . ?

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
C8 O2 Cu1 129.3(2) . 2 ?
O1 Cu1 O2 175.30(10) . 2_545 ?
O1 Cu1 N1 88.77(10) . . ?
O2 Cu1 N1 90.70(10) 2_545 . ?
O1 Cu1 N1 87.07(10) . 2_545 ?
O2 Cu1 N1 93.29(10) 2_545 2_545 ?
N1 Cu1 N1 175.42(2) . 2_545 ?
O1 Cu1 O5 91.56(10) . . ?
O2 Cu1 O5 93.05(10) 2_545 . ?
N1 Cu1 O5 85.26(11) . . ?
N1 Cu1 O5 96.75(11) 2_545 . ?
C8 O1 Cu1 134.5(2) . . ?
N2 N1 Cu1 120.7(2) . . ?
N2 N1 Cu1 116.2(2) . 2 ?
Cu1 N1 Cu1 110.40(12) . 2 ?
N3 N2 N1 177.7(4) . . ?
C6 C5 C10 115.4(3) . . ?
C6 C5 C16 126.1(3) . . ?
C10 C5 C16 118.5(3) . . ?
C7 C6 C5 123.4(3) . . ?
C7 C6 N4 115.9(3) . . ?
C5 C6 N4 120.8(3) . . ?
C12 C7 C6 119.0(3) . . ?
O2 C8 O1 127.7(3) . . ?
O2 C8 C16 119.7(3) . . ?
O1 C8 C16 112.6(3) . . ?
O4 N4 O3 123.8(3) . . ?
O4 N4 C6 118.8(3) . . ?
O3 N4 C6 117.5(3) . . ?
C14 C10 C5 122.0(3) . . ?
C14 C12 C7 119.5(3) . . ?
C12 C14 C10 120.6(3) . . ?
C5 C16 C8 117.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.14
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 972618'
