#==============================================================================
data_global
loop_
_journal_name_full                 'European Journal of Chemistry'
_journal_coden_ASTM                EJCUA9
_journal_volume                    10
_journal_issue                     3
_journal_year                      2019
_journal_page_first                195
_journal_page_last                 200
#===============================================================================
data_k12adb02

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H13 Cu N5 O4'
_chemical_formula_weight         318.78

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'

_symmetry_cell_setting            triclinic 
_symmetry_space_group_name_H-M    P-1

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

_cell_length_a                   7.9550(2)
_cell_length_b                   7.9810(2)
_cell_length_c                   11.0660(3)
_cell_angle_alpha                76.328(1)
_cell_angle_beta                 71.115(1)
_cell_angle_gamma                84.577(1)
_cell_volume                     645.79(3)
_cell_formula_units_Z            2
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     15243
_cell_measurement_theta_min        2.910
_cell_measurement_theta_max        27.485
 
_exptl_crystal_description        block 
_exptl_crystal_colour             red
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.639 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              326 
_exptl_absorpt_coefficient_mu     1.709 

# Absorption correction 

_exptl_absorpt_correction_type 'multi-scan' 
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  '95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11111
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2951
_reflns_number_gt                2410
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'Denzo & Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'

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

Asymmetric unit consist of one Cu(I) centre, 3 independent pyrazine 
halves, each of which straddles a crystallographic inversion centre, 
one nitrate anion and one guest DMF molecule.

Overall, the structure consists of parallel 2-D sheets. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0223P)^2^+0.2453P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2951
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.29077(4) 0.26089(3) 0.79824(2) 0.02253(10) Uani 1 1 d . . .
O1 O 0.0949(2) 0.0866(2) 0.80282(16) 0.0321(4) Uani 1 1 d . . .
O2 O 0.0577(2) -0.1660(2) 0.77473(19) 0.0425(5) Uani 1 1 d . . .
O3 O 0.3175(2) -0.0515(2) 0.69201(17) 0.0379(4) Uani 1 1 d . . .
O4 O 0.6154(2) 0.5179(2) 0.80893(18) 0.0388(4) Uani 1 1 d . . .
N1 N 0.4048(2) 0.3969(2) 0.62060(16) 0.0196(4) Uani 1 1 d . . .
N2 N 0.1171(2) 0.4088(2) 0.91297(17) 0.0210(4) Uani 1 1 d . . .
N3 N 0.4182(2) 0.1096(2) 0.91529(16) 0.0201(4) Uani 1 1 d . . .
N4 N 0.1571(3) -0.0461(2) 0.75650(18) 0.0246(4) Uani 1 1 d . . .
N5 N 0.7512(3) 0.7541(3) 0.6594(2) 0.0311(5) Uani 1 1 d . . .
C1 C 0.5035(3) 0.3286(3) 0.5194(2) 0.0208(5) Uani 1 1 d . . .
H1 H 0.5086 0.2069 0.5297 0.025 Uiso 1 1 calc R . .
C2 C 0.4024(3) 0.5706(3) 0.5989(2) 0.0201(5) Uani 1 1 d . . .
H2 H 0.3338 0.6252 0.6672 0.024 Uiso 1 1 calc R . .
C3 C 0.1734(3) 0.4899(3) 0.9850(2) 0.0241(5) Uani 1 1 d . . .
H3 H 0.2963 0.4854 0.9767 0.029 Uiso 1 1 calc R . .
C4 C -0.0576(3) 0.4197(3) 0.9289(2) 0.0238(5) Uani 1 1 d . . .
H4 H -0.1030 0.3637 0.8795 0.029 Uiso 1 1 calc R . .
C5 C 0.3281(3) -0.0125(3) 1.0159(2) 0.0233(5) Uani 1 1 d . . .
H5 H 0.2050 -0.0246 1.0305 0.028 Uiso 1 1 calc R . .
C6 C 0.5908(3) 0.1209(3) 0.9015(2) 0.0238(5) Uani 1 1 d . . .
H6 H 0.6595 0.2065 0.8325 0.029 Uiso 1 1 calc R . .
C7 C 0.6282(3) 0.6744(3) 0.7665(2) 0.0310(6) Uani 1 1 d . . .
H7 H 0.5425 0.7454 0.8145 0.037 Uiso 1 1 calc R . .
C8 C 0.7580(4) 0.9409(3) 0.6192(3) 0.0365(6) Uani 1 1 d . . .
H8A H 0.6504 0.9915 0.6721 0.055 Uiso 1 1 calc R . .
H8B H 0.7654 0.9764 0.5266 0.055 Uiso 1 1 calc R . .
H8C H 0.8627 0.9807 0.6317 0.055 Uiso 1 1 calc R . .
C9 C 0.8898(4) 0.6562(4) 0.5822(3) 0.0479(7) Uani 1 1 d . . .
H9A H 1.0042 0.6766 0.5912 0.072 Uiso 1 1 calc R . .
H9B H 0.8954 0.6928 0.4900 0.072 Uiso 1 1 calc R . .
H9C H 0.8635 0.5331 0.6131 0.072 Uiso 1 1 calc R . .

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 0.02470(16) 0.02090(15) 0.01916(15) -0.00260(11) -0.00449(11) 0.00036(11)
O1 0.0254(9) 0.0284(9) 0.0424(10) -0.0182(8) -0.0027(7) -0.0015(7)
O2 0.0443(11) 0.0286(9) 0.0577(12) -0.0115(9) -0.0153(9) -0.0130(8)
O3 0.0282(10) 0.0370(10) 0.0462(11) -0.0190(8) -0.0024(8) 0.0026(8)
O4 0.0417(11) 0.0305(10) 0.0487(11) -0.0053(8) -0.0224(9) -0.0007(8)
N1 0.0214(9) 0.0195(9) 0.0180(9) -0.0046(7) -0.0061(7) 0.0001(7)
N2 0.0226(9) 0.0203(9) 0.0196(9) -0.0031(7) -0.0067(8) -0.0005(8)
N3 0.0200(9) 0.0181(9) 0.0196(9) -0.0031(7) -0.0033(7) -0.0015(7)
N4 0.0294(11) 0.0221(10) 0.0237(10) -0.0042(8) -0.0101(9) -0.0024(8)
N5 0.0294(11) 0.0307(11) 0.0350(11) -0.0135(9) -0.0094(9) 0.0052(9)
C1 0.0253(11) 0.0172(10) 0.0210(11) -0.0040(9) -0.0091(9) 0.0004(9)
C2 0.0226(11) 0.0199(11) 0.0187(11) -0.0062(9) -0.0064(9) 0.0008(9)
C3 0.0195(11) 0.0265(12) 0.0268(12) -0.0061(10) -0.0079(9) -0.0001(9)
C4 0.0254(12) 0.0264(12) 0.0239(11) -0.0101(10) -0.0101(10) -0.0015(10)
C5 0.0187(11) 0.0246(11) 0.0229(11) -0.0024(9) -0.0030(9) -0.0026(9)
C6 0.0250(12) 0.0220(11) 0.0203(11) -0.0003(9) -0.0033(9) -0.0048(9)
C7 0.0308(13) 0.0356(14) 0.0326(13) -0.0115(11) -0.0164(11) 0.0045(11)
C8 0.0381(15) 0.0347(14) 0.0341(14) -0.0057(11) -0.0097(12) 0.0022(12)
C9 0.0407(16) 0.0493(17) 0.0542(18) -0.0266(14) -0.0076(14) 0.0090(14)

_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 N1 1.9720(17) . ?
Cu1 N3 2.0108(17) . ?
Cu1 N2 2.0443(18) . ?
Cu1 O1 2.1660(16) . ?
O1 N4 1.274(2) . ?
O2 N4 1.237(2) . ?
O3 N4 1.246(2) . ?
O4 C7 1.227(3) . ?
N1 C1 1.344(3) . ?
N1 C2 1.349(3) . ?
N2 C3 1.335(3) . ?
N2 C4 1.340(3) . ?
N3 C6 1.341(3) . ?
N3 C5 1.344(3) . ?
N5 C7 1.333(3) . ?
N5 C9 1.449(3) . ?
N5 C8 1.452(3) . ?
C1 C2 1.380(3) 2_666 ?
C1 H1 0.9500 . ?
C2 C1 1.380(3) 2_666 ?
C2 H2 0.9500 . ?
C3 C4 1.382(3) 2_567 ?
C3 H3 0.9500 . ?
C4 C3 1.382(3) 2_567 ?
C4 H4 0.9500 . ?
C5 C6 1.380(3) 2_657 ?
C5 H5 0.9500 . ?
C6 C5 1.380(3) 2_657 ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
N1 Cu1 N3 125.60(7) . . ?
N1 Cu1 N2 111.52(7) . . ?
N3 Cu1 N2 105.15(7) . . ?
N1 Cu1 O1 112.54(7) . . ?
N3 Cu1 O1 101.48(7) . . ?
N2 Cu1 O1 96.28(7) . . ?
N4 O1 Cu1 115.53(13) . . ?
C1 N1 C2 115.77(17) . . ?
C1 N1 Cu1 124.28(14) . . ?
C2 N1 Cu1 119.56(14) . . ?
C3 N2 C4 116.43(18) . . ?
C3 N2 Cu1 120.06(14) . . ?
C4 N2 Cu1 123.31(15) . . ?
C6 N3 C5 115.88(18) . . ?
C6 N3 Cu1 124.67(14) . . ?
C5 N3 Cu1 119.45(14) . . ?
O2 N4 O3 121.20(19) . . ?
O2 N4 O1 119.75(19) . . ?
O3 N4 O1 119.05(19) . . ?
C7 N5 C9 120.7(2) . . ?
C7 N5 C8 121.9(2) . . ?
C9 N5 C8 117.3(2) . . ?
N1 C1 C2 122.22(19) . 2_666 ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 2_666 . ?
N1 C2 C1 122.01(19) . 2_666 ?
N1 C2 H2 119.0 . . ?
C1 C2 H2 119.0 2_666 . ?
N2 C3 C4 121.7(2) . 2_567 ?
N2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 2_567 . ?
N2 C4 C3 121.8(2) . 2_567 ?
N2 C4 H4 119.1 . . ?
C3 C4 H4 119.1 2_567 . ?
N3 C5 C6 121.9(2) . 2_657 ?
N3 C5 H5 119.1 . . ?
C6 C5 H5 119.1 2_657 . ?
N3 C6 C5 122.22(19) . 2_657 ?
N3 C6 H6 118.9 . . ?
C5 C6 H6 118.9 2_657 . ?
O4 C7 N5 126.1(2) . . ?
O4 C7 H7 117.0 . . ?
N5 C7 H7 117.0 . . ?
N5 C8 H8A 109.5 . . ?
N5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N5 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
N1 Cu1 O1 N4 74.01(16) . . . . ?
N3 Cu1 O1 N4 -62.66(15) . . . . ?
N2 Cu1 O1 N4 -169.56(14) . . . . ?
N3 Cu1 N1 C1 61.63(19) . . . . ?
N2 Cu1 N1 C1 -169.49(16) . . . . ?
O1 Cu1 N1 C1 -62.58(18) . . . . ?
N3 Cu1 N1 C2 -110.90(16) . . . . ?
N2 Cu1 N1 C2 17.98(18) . . . . ?
O1 Cu1 N1 C2 124.89(16) . . . . ?
N1 Cu1 N2 C3 -90.51(16) . . . . ?
N3 Cu1 N2 C3 48.51(17) . . . . ?
O1 Cu1 N2 C3 152.24(16) . . . . ?
N1 Cu1 N2 C4 94.87(17) . . . . ?
N3 Cu1 N2 C4 -126.11(17) . . . . ?
O1 Cu1 N2 C4 -22.38(17) . . . . ?
N1 Cu1 N3 C6 19.3(2) . . . . ?
N2 Cu1 N3 C6 -112.07(18) . . . . ?
O1 Cu1 N3 C6 148.10(17) . . . . ?
N1 Cu1 N3 C5 -161.00(15) . . . . ?
N2 Cu1 N3 C5 67.61(17) . . . . ?
O1 Cu1 N3 C5 -32.21(17) . . . . ?
Cu1 O1 N4 O2 167.97(15) . . . . ?
Cu1 O1 N4 O3 -12.9(2) . . . . ?
C2 N1 C1 C2 0.5(3) . . . 2_666 ?
Cu1 N1 C1 C2 -172.30(16) . . . 2_666 ?
C1 N1 C2 C1 -0.5(3) . . . 2_666 ?
Cu1 N1 C2 C1 172.66(16) . . . 2_666 ?
C4 N2 C3 C4 0.0(3) . . . 2_567 ?
Cu1 N2 C3 C4 -175.01(16) . . . 2_567 ?
C3 N2 C4 C3 0.0(3) . . . 2_567 ?
Cu1 N2 C4 C3 174.83(16) . . . 2_567 ?
C6 N3 C5 C6 -0.9(4) . . . 2_657 ?
Cu1 N3 C5 C6 179.39(16) . . . 2_657 ?
C5 N3 C6 C5 0.9(4) . . . 2_657 ?
Cu1 N3 C6 C5 -179.41(16) . . . 2_657 ?
C9 N5 C7 O4 -1.6(4) . . . . ?
C8 N5 C7 O4 -178.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.091

data_c:\users\swifts\desktop\k12adb02\k12adb02 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C9 H13 Cu N5 O4' 
_chemical_formula_weight          318.78 
 
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' 
 
_symmetry_cell_setting            ? 
_symmetry_space_group_name_H-M    ? 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    7.9550(2) 
_cell_length_b                    7.9810(2) 
_cell_length_c                    11.0660(3) 
_cell_angle_alpha                 76.3280(10) 
_cell_angle_beta                  71.1150(10) 
_cell_angle_gamma                 84.5770(10) 
_cell_volume                      645.79(3) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.639 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              326 
_exptl_absorpt_coefficient_mu     1.709 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   0.7261 
_exptl_absorpt_correction_T_max   0.9194 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(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             11111 
_diffrn_reflns_av_R_equivalents   0.0539 
_diffrn_reflns_av_sigmaI/netI     0.0556 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          3.50 
_diffrn_reflns_theta_max          27.48 
_reflns_number_total              2951 
_reflns_number_gt                 2410 
_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 F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0223P)^2^+0.2453P] where P=(Fo^2^+2Fc^2^)/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          2951 
_refine_ls_number_parameters      174 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0524 
_refine_ls_R_factor_gt            0.0346 
_refine_ls_wR_factor_ref          0.0727 
_refine_ls_wR_factor_gt           0.0669 
_refine_ls_goodness_of_fit_ref    1.054 
_refine_ls_restrained_S_all       1.054 
_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_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
Cu1 Cu 0.29077(4) 0.26089(3) 0.79824(2) 0.02253(10) Uani 1 1 d . . . 
O1 O 0.0949(2) 0.0866(2) 0.80282(16) 0.0321(4) Uani 1 1 d . . . 
O2 O 0.0577(2) -0.1660(2) 0.77473(19) 0.0425(5) Uani 1 1 d . . . 
O3 O 0.3175(2) -0.0515(2) 0.69201(17) 0.0379(4) Uani 1 1 d . . . 
O4 O 0.6154(2) 0.5179(2) 0.80893(18) 0.0388(4) Uani 1 1 d . . . 
N1 N 0.4048(2) 0.3969(2) 0.62060(16) 0.0196(4) Uani 1 1 d . . . 
N2 N 0.1171(2) 0.4088(2) 0.91297(17) 0.0210(4) Uani 1 1 d . . . 
N3 N 0.4182(2) 0.1096(2) 0.91529(16) 0.0201(4) Uani 1 1 d . . . 
N4 N 0.1571(3) -0.0461(2) 0.75650(18) 0.0246(4) Uani 1 1 d . . . 
N5 N 0.7512(3) 0.7541(3) 0.6594(2) 0.0311(5) Uani 1 1 d . . . 
C1 C 0.5035(3) 0.3286(3) 0.5194(2) 0.0208(5) Uani 1 1 d . . . 
H1 H 0.5086 0.2069 0.5297 0.025 Uiso 1 1 calc R . . 
C2 C 0.4024(3) 0.5706(3) 0.5989(2) 0.0201(5) Uani 1 1 d . . . 
H2 H 0.3338 0.6252 0.6672 0.024 Uiso 1 1 calc R . . 
C3 C 0.1734(3) 0.4899(3) 0.9850(2) 0.0241(5) Uani 1 1 d . . . 
H3 H 0.2963 0.4854 0.9767 0.029 Uiso 1 1 calc R . . 
C4 C -0.0576(3) 0.4197(3) 0.9289(2) 0.0238(5) Uani 1 1 d . . . 
H4 H -0.1030 0.3637 0.8795 0.029 Uiso 1 1 calc R . . 
C5 C 0.3281(3) -0.0125(3) 1.0159(2) 0.0233(5) Uani 1 1 d . . . 
H5 H 0.2050 -0.0246 1.0305 0.028 Uiso 1 1 calc R . . 
C6 C 0.5908(3) 0.1209(3) 0.9015(2) 0.0238(5) Uani 1 1 d . . . 
H6 H 0.6595 0.2065 0.8325 0.029 Uiso 1 1 calc R . . 
C7 C 0.6282(3) 0.6744(3) 0.7665(2) 0.0310(6) Uani 1 1 d . . . 
H7 H 0.5425 0.7454 0.8145 0.037 Uiso 1 1 calc R . . 
C8 C 0.7580(4) 0.9409(3) 0.6192(3) 0.0365(6) Uani 1 1 d . . . 
H8A H 0.6504 0.9915 0.6721 0.055 Uiso 1 1 calc R . . 
H8B H 0.7654 0.9764 0.5266 0.055 Uiso 1 1 calc R . . 
H8C H 0.8627 0.9807 0.6317 0.055 Uiso 1 1 calc R . . 
C9 C 0.8898(4) 0.6562(4) 0.5822(3) 0.0479(7) Uani 1 1 d . . . 
H9A H 1.0042 0.6766 0.5912 0.072 Uiso 1 1 calc R . . 
H9B H 0.8954 0.6928 0.4900 0.072 Uiso 1 1 calc R . . 
H9C H 0.8635 0.5331 0.6131 0.072 Uiso 1 1 calc R . . 
 
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 0.02470(16) 0.02090(15) 0.01916(15) -0.00260(11) -0.00449(11) 0.00036(11) 
O1 0.0254(9) 0.0284(9) 0.0424(10) -0.0182(8) -0.0027(7) -0.0015(7) 
O2 0.0443(11) 0.0286(9) 0.0577(12) -0.0115(9) -0.0153(9) -0.0130(8) 
O3 0.0282(10) 0.0370(10) 0.0462(11) -0.0190(8) -0.0024(8) 0.0026(8) 
O4 0.0417(11) 0.0305(10) 0.0487(11) -0.0053(8) -0.0224(9) -0.0007(8) 
N1 0.0214(9) 0.0195(9) 0.0180(9) -0.0046(7) -0.0061(7) 0.0001(7) 
N2 0.0226(9) 0.0203(9) 0.0196(9) -0.0031(7) -0.0067(8) -0.0005(8) 
N3 0.0200(9) 0.0181(9) 0.0196(9) -0.0031(7) -0.0033(7) -0.0015(7) 
N4 0.0294(11) 0.0221(10) 0.0237(10) -0.0042(8) -0.0101(9) -0.0024(8) 
N5 0.0294(11) 0.0307(11) 0.0350(11) -0.0135(9) -0.0094(9) 0.0052(9) 
C1 0.0253(11) 0.0172(10) 0.0210(11) -0.0040(9) -0.0091(9) 0.0004(9) 
C2 0.0226(11) 0.0199(11) 0.0187(11) -0.0062(9) -0.0064(9) 0.0008(9) 
C3 0.0195(11) 0.0265(12) 0.0268(12) -0.0061(10) -0.0079(9) -0.0001(9) 
C4 0.0254(12) 0.0264(12) 0.0239(11) -0.0101(10) -0.0101(10) -0.0015(10) 
C5 0.0187(11) 0.0246(11) 0.0229(11) -0.0024(9) -0.0030(9) -0.0026(9) 
C6 0.0250(12) 0.0220(11) 0.0203(11) -0.0003(9) -0.0033(9) -0.0048(9) 
C7 0.0308(13) 0.0356(14) 0.0326(13) -0.0115(11) -0.0164(11) 0.0045(11) 
C8 0.0381(15) 0.0347(14) 0.0341(14) -0.0057(11) -0.0097(12) 0.0022(12) 
C9 0.0407(16) 0.0493(17) 0.0542(18) -0.0266(14) -0.0076(14) 0.0090(14) 
 
_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 N1 1.9720(17) . ? 
Cu1 N3 2.0108(17) . ? 
Cu1 N2 2.0443(18) . ? 
Cu1 O1 2.1660(16) . ? 
O1 N4 1.274(2) . ? 
O2 N4 1.237(2) . ? 
O3 N4 1.246(2) . ? 
O4 C7 1.227(3) . ? 
N1 C1 1.344(3) . ? 
N1 C2 1.349(3) . ? 
N2 C3 1.335(3) . ? 
N2 C4 1.340(3) . ? 
N3 C6 1.341(3) . ? 
N3 C5 1.344(3) . ? 
N5 C7 1.333(3) . ? 
N5 C9 1.449(3) . ? 
N5 C8 1.452(3) . ? 
C1 C2 1.380(3) 2_666 ? 
C1 H1 0.9500 . ? 
C2 C1 1.380(3) 2_666 ? 
C2 H2 0.9500 . ? 
C3 C4 1.382(3) 2_567 ? 
C3 H3 0.9500 . ? 
C4 C3 1.382(3) 2_567 ? 
C4 H4 0.9500 . ? 
C5 C6 1.380(3) 2_657 ? 
C5 H5 0.9500 . ? 
C6 C5 1.380(3) 2_657 ? 
C6 H6 0.9500 . ? 
C7 H7 0.9500 . ? 
C8 H8A 0.9800 . ? 
C8 H8B 0.9800 . ? 
C8 H8C 0.9800 . ? 
C9 H9A 0.9800 . ? 
C9 H9B 0.9800 . ? 
C9 H9C 0.9800 . ? 
 
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 
N1 Cu1 N3 125.60(7) . . ? 
N1 Cu1 N2 111.52(7) . . ? 
N3 Cu1 N2 105.15(7) . . ? 
N1 Cu1 O1 112.54(7) . . ? 
N3 Cu1 O1 101.48(7) . . ? 
N2 Cu1 O1 96.28(7) . . ? 
N4 O1 Cu1 115.53(13) . . ? 
C1 N1 C2 115.77(17) . . ? 
C1 N1 Cu1 124.28(14) . . ? 
C2 N1 Cu1 119.56(14) . . ? 
C3 N2 C4 116.43(18) . . ? 
C3 N2 Cu1 120.06(14) . . ? 
C4 N2 Cu1 123.31(15) . . ? 
C6 N3 C5 115.88(18) . . ? 
C6 N3 Cu1 124.67(14) . . ? 
C5 N3 Cu1 119.45(14) . . ? 
O2 N4 O3 121.20(19) . . ? 
O2 N4 O1 119.75(19) . . ? 
O3 N4 O1 119.05(19) . . ? 
C7 N5 C9 120.7(2) . . ? 
C7 N5 C8 121.9(2) . . ? 
C9 N5 C8 117.3(2) . . ? 
N1 C1 C2 122.22(19) . 2_666 ? 
N1 C1 H1 118.9 . . ? 
C2 C1 H1 118.9 2_666 . ? 
N1 C2 C1 122.01(19) . 2_666 ? 
N1 C2 H2 119.0 . . ? 
C1 C2 H2 119.0 2_666 . ? 
N2 C3 C4 121.7(2) . 2_567 ? 
N2 C3 H3 119.1 . . ? 
C4 C3 H3 119.1 2_567 . ? 
N2 C4 C3 121.8(2) . 2_567 ? 
N2 C4 H4 119.1 . . ? 
C3 C4 H4 119.1 2_567 . ? 
N3 C5 C6 121.9(2) . 2_657 ? 
N3 C5 H5 119.1 . . ? 
C6 C5 H5 119.1 2_657 . ? 
N3 C6 C5 122.22(19) . 2_657 ? 
N3 C6 H6 118.9 . . ? 
C5 C6 H6 118.9 2_657 . ? 
O4 C7 N5 126.1(2) . . ? 
O4 C7 H7 117.0 . . ? 
N5 C7 H7 117.0 . . ? 
N5 C8 H8A 109.5 . . ? 
N5 C8 H8B 109.5 . . ? 
H8A C8 H8B 109.5 . . ? 
N5 C8 H8C 109.5 . . ? 
H8A C8 H8C 109.5 . . ? 
H8B C8 H8C 109.5 . . ? 
N5 C9 H9A 109.5 . . ? 
N5 C9 H9B 109.5 . . ? 
H9A C9 H9B 109.5 . . ? 
N5 C9 H9C 109.5 . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 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 
N1 Cu1 O1 N4 74.01(16) . . . . ? 
N3 Cu1 O1 N4 -62.66(15) . . . . ? 
N2 Cu1 O1 N4 -169.56(14) . . . . ? 
N3 Cu1 N1 C1 61.63(19) . . . . ? 
N2 Cu1 N1 C1 -169.49(16) . . . . ? 
O1 Cu1 N1 C1 -62.58(18) . . . . ? 
N3 Cu1 N1 C2 -110.90(16) . . . . ? 
N2 Cu1 N1 C2 17.98(18) . . . . ? 
O1 Cu1 N1 C2 124.89(16) . . . . ? 
N1 Cu1 N2 C3 -90.51(16) . . . . ? 
N3 Cu1 N2 C3 48.51(17) . . . . ? 
O1 Cu1 N2 C3 152.24(16) . . . . ? 
N1 Cu1 N2 C4 94.87(17) . . . . ? 
N3 Cu1 N2 C4 -126.11(17) . . . . ? 
O1 Cu1 N2 C4 -22.38(17) . . . . ? 
N1 Cu1 N3 C6 19.3(2) . . . . ? 
N2 Cu1 N3 C6 -112.07(18) . . . . ? 
O1 Cu1 N3 C6 148.10(17) . . . . ? 
N1 Cu1 N3 C5 -161.00(15) . . . . ? 
N2 Cu1 N3 C5 67.61(17) . . . . ? 
O1 Cu1 N3 C5 -32.21(17) . . . . ? 
Cu1 O1 N4 O2 167.97(15) . . . . ? 
Cu1 O1 N4 O3 -12.9(2) . . . . ? 
C2 N1 C1 C2 0.5(3) . . . 2_666 ? 
Cu1 N1 C1 C2 -172.30(16) . . . 2_666 ? 
C1 N1 C2 C1 -0.5(3) . . . 2_666 ? 
Cu1 N1 C2 C1 172.66(16) . . . 2_666 ? 
C4 N2 C3 C4 0.0(3) . . . 2_567 ? 
Cu1 N2 C3 C4 -175.01(16) . . . 2_567 ? 
C3 N2 C4 C3 0.0(3) . . . 2_567 ? 
Cu1 N2 C4 C3 174.83(16) . . . 2_567 ? 
C6 N3 C5 C6 -0.9(4) . . . 2_657 ? 
Cu1 N3 C5 C6 179.39(16) . . . 2_657 ? 
C5 N3 C6 C5 0.9(4) . . . 2_657 ? 
Cu1 N3 C6 C5 -179.41(16) . . . 2_657 ? 
C9 N5 C7 O4 -1.6(4) . . . . ? 
C8 N5 C7 O4 -178.3(2) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.995 
_diffrn_reflns_theta_full              27.48 
_diffrn_measured_fraction_theta_full   0.995 
_refine_diff_density_max    0.316 
_refine_diff_density_min   -0.649 
_refine_diff_density_rms    0.091 
