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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_gg

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Cu2 N6'
_chemical_formula_sum            'C16 H14 Cu2 N6'
_chemical_formula_weight         417.41

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   8.7916(4)
_cell_length_b                   15.3787(7)
_cell_length_c                   14.4000(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 122.692(2)
_cell_angle_gamma                90.00
_cell_volume                     1638.51(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7116
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      27.56

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    2.605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5980
_exptl_absorpt_correction_T_max  0.6374
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12449
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2906
_reflns_number_gt                2608
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0337P)²+1.0275P] where P=(Fo²+2Fc²)/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         2906
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0696
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
C9 C 0.3744(4) 0.98032(17) -0.1087(2) 0.0478(6) Uani 1 1 d . . .
Cu1 Cu 1.39555(4) 0.963843(19) 0.52530(2) 0.04439(11) Uani 1 1 d U . .
Cu2 Cu 1.39184(4) 0.738376(19) 0.76643(2) 0.03950(11) Uani 1 1 d . . .
N2 N 1.4438(3) 0.86051(14) 0.62197(17) 0.0465(5) Uani 1 1 d . . .
N1 N 1.5171(3) 1.14024(14) 0.63676(18) 0.0469(5) Uani 1 1 d . . .
N3 N 1.1338(3) 0.93798(12) 0.40424(15) 0.0364(4) Uani 1 1 d . . .
N4 N 0.8906(3) 0.89415(13) 0.25068(16) 0.0385(5) Uani 1 1 d . . .
N5 N 1.1727(3) 0.77830(12) 0.77108(17) 0.0386(5) Uani 1 1 d . . .
N6 N 1.0070(3) 0.81439(12) 0.83705(17) 0.0396(5) Uani 1 1 d . . .
C2 C 1.4321(3) 0.80996(16) 0.67601(19) 0.0393(5) Uani 1 1 d . . .
C1 C 1.4809(3) 1.07738(17) 0.5866(2) 0.0418(6) Uani 1 1 d U . .
C3 C 1.0014(4) 0.91661(16) 0.4236(2) 0.0462(6) Uani 1 1 d . . .
H3 H 1.0139 0.9202 0.4918 0.055 Uiso 1 1 calc R . .
C4 C 0.8516(4) 0.88975(17) 0.3300(2) 0.0474(6) Uani 1 1 d . . .
H4 H 0.7435 0.8719 0.3212 0.057 Uiso 1 1 calc R . .
C5 C 1.0599(3) 0.92415(14) 0.29851(18) 0.0343(5) Uani 1 1 d . . .
H5 H 1.1178 0.9339 0.2613 0.041 Uiso 1 1 calc R . .
C6 C 0.7720(4) 0.87087(18) 0.1346(2) 0.0537(7) Uani 1 1 d . . .
H6A H 0.7114 0.8166 0.1293 0.064 Uiso 1 1 calc R . .
H6B H 0.8448 0.8614 0.1035 0.064 Uiso 1 1 calc R . .
C7 C 0.6316(3) 0.93923(15) 0.0675(2) 0.0402(5) Uani 1 1 d . . .
C8 C 0.5045(3) 0.92047(16) -0.0415(2) 0.0455(6) Uani 1 1 d . . .
H8 H 0.5066 0.8666 -0.0701 0.055 Uiso 1 1 calc R . .
H9 H 0.2901 0.9667 -0.1821 0.055 Uiso 1 1 d R . .
C10 C 1.1571(3) 0.77397(15) 0.8568(2) 0.0374(5) Uani 1 1 d . . .
H10 H 1.2397 0.7464 0.9228 0.045 Uiso 1 1 calc R . .
C11 C 1.0240(4) 0.82455(16) 0.6926(2) 0.0441(6) Uani 1 1 d . . .
H11 H 0.9984 0.8381 0.6226 0.053 Uiso 1 1 calc R . .
C12 C 0.9207(4) 0.84749(17) 0.7320(2) 0.0457(6) Uani 1 1 d . . .
H12 H 0.8136 0.8791 0.6955 0.055 Uiso 1 1 calc R . .
C13 C 0.9491(4) 0.82397(17) 0.9148(3) 0.0541(7) Uani 1 1 d . . .
H13A H 1.0174 0.7841 0.9759 0.065 Uiso 1 1 calc R . .
H13B H 0.8223 0.8086 0.8779 0.065 Uiso 1 1 calc R . .
C14 C 0.9756(4) 0.91562(16) 0.9591(2) 0.0435(6) Uani 1 1 d . . .
C15 C 1.1392(4) 0.94072(18) 1.0506(2) 0.0498(6) Uani 1 1 d . . .
H15 H 1.2335 0.9009 1.0851 0.060 Uiso 1 1 calc R . .
C16 C 0.8357(4) 0.97579(18) 0.9084(2) 0.0497(7) Uani 1 1 d . . .
H16 H 0.7248 0.9597 0.8467 0.060 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
C9 0.0394(14) 0.0416(14) 0.0375(13) -0.0076(11) 0.0045(11) 0.0006(12)
Cu1 0.0544(2) 0.03357(18) 0.03732(18) -0.00099(12) 0.01963(16) -0.01369(14)
Cu2 0.0487(2) 0.03395(17) 0.04397(18) 0.00897(12) 0.03036(16) 0.00257(13)
N2 0.0458(12) 0.0486(13) 0.0397(11) 0.0090(10) 0.0195(10) -0.0049(10)
N1 0.0506(13) 0.0458(13) 0.0590(13) -0.0192(11) 0.0392(12) -0.0127(11)
N3 0.0437(11) 0.0294(10) 0.0352(10) 0.0029(8) 0.0207(9) -0.0009(9)
N4 0.0341(11) 0.0356(11) 0.0384(10) 0.0047(8) 0.0146(9) 0.0063(9)
N5 0.0469(12) 0.0300(10) 0.0468(11) 0.0046(9) 0.0305(10) 0.0033(9)
N6 0.0492(12) 0.0307(10) 0.0503(12) -0.0088(9) 0.0342(11) -0.0048(9)
C2 0.0382(13) 0.0402(13) 0.0399(12) 0.0084(11) 0.0213(11) 0.0012(11)
C1 0.0422(14) 0.0424(14) 0.0457(13) -0.0107(11) 0.0269(12) -0.0079(12)
C3 0.0650(18) 0.0396(14) 0.0487(14) 0.0047(11) 0.0404(15) 0.0046(13)
C4 0.0414(14) 0.0449(15) 0.0636(17) 0.0080(13) 0.0336(14) 0.0035(12)
C5 0.0368(12) 0.0323(12) 0.0359(12) 0.0066(9) 0.0209(11) 0.0043(10)
C6 0.0466(15) 0.0431(15) 0.0444(14) -0.0030(12) 0.0070(13) 0.0104(13)
C7 0.0319(12) 0.0337(12) 0.0416(13) -0.0001(10) 0.0109(11) 0.0004(10)
C8 0.0398(14) 0.0319(12) 0.0464(14) -0.0077(11) 0.0111(12) 0.0007(11)
C10 0.0461(14) 0.0275(11) 0.0417(13) -0.0004(10) 0.0256(12) -0.0024(11)
C11 0.0546(16) 0.0382(13) 0.0432(13) 0.0040(11) 0.0288(13) 0.0025(12)
C12 0.0449(14) 0.0374(13) 0.0514(15) -0.0004(11) 0.0237(13) 0.0051(12)
C13 0.077(2) 0.0403(15) 0.0736(18) -0.0154(13) 0.0598(18) -0.0119(14)
C14 0.0593(16) 0.0379(13) 0.0523(14) -0.0084(11) 0.0425(14) -0.0048(12)
C15 0.0552(16) 0.0470(15) 0.0551(16) -0.0004(12) 0.0349(14) 0.0085(13)
C16 0.0475(15) 0.0529(16) 0.0533(15) -0.0132(13) 0.0303(14) -0.0052(13)

_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
C9 C8 1.377(4) . ?
C9 C7 1.386(3) 3_675 ?
C9 H9 0.9297 . ?
Cu1 C1 1.917(3) . ?
Cu1 N2 2.001(2) . ?
Cu1 N3 2.040(2) . ?
Cu1 C1 2.464(2) 3_876 ?
Cu1 Cu1 2.5664(6) 3_876 ?
Cu2 C2 1.879(2) . ?
Cu2 N1 1.912(2) 2_846 ?
Cu2 N5 2.057(2) . ?
N2 C2 1.143(3) . ?
N1 C1 1.144(3) . ?
N1 Cu2 1.912(2) 2_856 ?
N3 C5 1.310(3) . ?
N3 C3 1.374(3) . ?
N4 C5 1.339(3) . ?
N4 C4 1.360(3) . ?
N4 C6 1.458(3) . ?
N5 C10 1.315(3) . ?
N5 C11 1.377(3) . ?
N6 C10 1.343(3) . ?
N6 C12 1.373(3) . ?
N6 C13 1.466(3) . ?
C1 Cu1 2.464(2) 3_876 ?
C3 C4 1.343(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.508(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.379(3) . ?
C7 C9 1.386(3) 3_675 ?
C8 H8 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.352(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.512(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.381(4) . ?
C14 C16 1.390(4) . ?
C15 C16 1.380(4) 3_777 ?
C15 H15 0.9300 . ?
C16 C15 1.380(4) 3_777 ?
C16 H16 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
C8 C9 C7 120.3(2) . 3_675 ?
C8 C9 H9 119.8 . . ?
C7 C9 H9 119.8 3_675 . ?
C1 Cu1 N2 121.31(10) . . ?
C1 Cu1 N3 123.47(10) . . ?
N2 Cu1 N3 99.04(8) . . ?
C1 Cu1 C1 109.54(8) . 3_876 ?
N2 Cu1 C1 104.35(9) . 3_876 ?
N3 Cu1 C1 94.78(8) . 3_876 ?
C1 Cu1 Cu1 64.79(7) . 3_876 ?
N2 Cu1 Cu1 128.77(7) . 3_876 ?
N3 Cu1 Cu1 119.47(5) . 3_876 ?
C1 Cu1 Cu1 44.75(6) 3_876 3_876 ?
C2 Cu2 N1 143.72(10) . 2_846 ?
C2 Cu2 N5 112.21(9) . . ?
N1 Cu2 N5 104.03(8) 2_846 . ?
C2 N2 Cu1 161.8(2) . . ?
C1 N1 Cu2 172.4(2) . 2_856 ?
C5 N3 C3 104.7(2) . . ?
C5 N3 Cu1 130.33(17) . . ?
C3 N3 Cu1 124.15(16) . . ?
C5 N4 C4 107.4(2) . . ?
C5 N4 C6 125.6(2) . . ?
C4 N4 C6 127.0(2) . . ?
C10 N5 C11 105.2(2) . . ?
C10 N5 Cu2 126.13(17) . . ?
C11 N5 Cu2 128.17(16) . . ?
C10 N6 C12 107.4(2) . . ?
C10 N6 C13 126.3(2) . . ?
C12 N6 C13 126.2(2) . . ?
N2 C2 Cu2 171.9(2) . . ?
N1 C1 Cu1 165.1(2) . . ?
N1 C1 Cu1 124.0(2) . 3_876 ?
Cu1 C1 Cu1 70.46(8) . 3_876 ?
C4 C3 N3 110.4(2) . . ?
C4 C3 H3 124.8 . . ?
N3 C3 H3 124.8 . . ?
C3 C4 N4 105.8(2) . . ?
C3 C4 H4 127.1 . . ?
N4 C4 H4 127.1 . . ?
N3 C5 N4 111.7(2) . . ?
N3 C5 H5 124.2 . . ?
N4 C5 H5 124.2 . . ?
N4 C6 C7 113.3(2) . . ?
N4 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N4 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C9 118.7(2) . 3_675 ?
C8 C7 C6 117.6(2) . . ?
C9 C7 C6 123.7(2) 3_675 . ?
C9 C8 C7 121.0(2) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
N5 C10 N6 111.5(2) . . ?
N5 C10 H10 124.2 . . ?
N6 C10 H10 124.2 . . ?
C12 C11 N5 110.2(2) . . ?
C12 C11 H11 124.9 . . ?
N5 C11 H11 124.9 . . ?
C11 C12 N6 105.6(2) . . ?
C11 C12 H12 127.2 . . ?
N6 C12 H12 127.2 . . ?
N6 C13 C14 112.2(2) . . ?
N6 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N6 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C16 119.0(2) . . ?
C15 C14 C13 120.5(3) . . ?
C16 C14 C13 120.5(3) . . ?
C16 C15 C14 120.8(3) 3_777 . ?
C16 C15 H15 119.6 3_777 . ?
C14 C15 H15 119.6 . . ?
C15 C16 C14 120.2(3) 3_777 . ?
C15 C16 H16 119.9 3_777 . ?
C14 C16 H16 119.9 . . ?

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
C1 Cu1 N2 C2 83.3(7) . . . . ?
N3 Cu1 N2 C2 -55.4(7) . . . . ?
C1 Cu1 N2 C2 -152.7(7) 3_876 . . . ?
Cu1 Cu1 N2 C2 164.6(6) 3_876 . . . ?
C1 Cu1 N3 C5 103.7(2) . . . . ?
N2 Cu1 N3 C5 -118.9(2) . . . . ?
C1 Cu1 N3 C5 -13.5(2) 3_876 . . . ?
Cu1 Cu1 N3 C5 26.0(2) 3_876 . . . ?
C1 Cu1 N3 C3 -88.2(2) . . . . ?
N2 Cu1 N3 C3 49.2(2) . . . . ?
C1 Cu1 N3 C3 154.56(19) 3_876 . . . ?
Cu1 Cu1 N3 C3 -165.92(16) 3_876 . . . ?
C2 Cu2 N5 C10 -144.8(2) . . . . ?
N1 Cu2 N5 C10 33.6(2) 2_846 . . . ?
C2 Cu2 N5 C11 26.0(2) . . . . ?
N1 Cu2 N5 C11 -155.5(2) 2_846 . . . ?
Cu1 N2 C2 Cu2 -17(2) . . . . ?
N1 Cu2 C2 N2 -160.5(15) 2_846 . . . ?
N5 Cu2 C2 N2 17.0(17) . . . . ?
Cu2 N1 C1 Cu1 93.6(18) 2_856 . . . ?
Cu2 N1 C1 Cu1 -72.2(17) 2_856 . . 3_876 ?
N2 Cu1 C1 N1 -46.0(10) . . . . ?
N3 Cu1 C1 N1 82.5(10) . . . . ?
C1 Cu1 C1 N1 -167.6(10) 3_876 . . . ?
Cu1 Cu1 C1 N1 -167.6(10) 3_876 . . . ?
N2 Cu1 C1 Cu1 121.58(9) . . . 3_876 ?
N3 Cu1 C1 Cu1 -109.91(8) . . . 3_876 ?
C1 Cu1 C1 Cu1 0.0 3_876 . . 3_876 ?
C5 N3 C3 C4 0.5(3) . . . . ?
Cu1 N3 C3 C4 -170.08(17) . . . . ?
N3 C3 C4 N4 0.1(3) . . . . ?
C5 N4 C4 C3 -0.7(3) . . . . ?
C6 N4 C4 C3 179.3(2) . . . . ?
C3 N3 C5 N4 -1.0(3) . . . . ?
Cu1 N3 C5 N4 168.80(15) . . . . ?
C4 N4 C5 N3 1.1(3) . . . . ?
C6 N4 C5 N3 -178.9(2) . . . . ?
C5 N4 C6 C7 -102.1(3) . . . . ?
C4 N4 C6 C7 77.8(3) . . . . ?
N4 C6 C7 C8 -175.3(2) . . . . ?
N4 C6 C7 C9 5.8(4) . . . 3_675 ?
C7 C9 C8 C7 -0.3(5) 3_675 . . . ?
C9 C7 C8 C9 0.3(5) 3_675 . . . ?
C6 C7 C8 C9 -178.6(3) . . . . ?
C11 N5 C10 N6 0.3(3) . . . . ?
Cu2 N5 C10 N6 172.81(15) . . . . ?
C12 N6 C10 N5 -0.4(3) . . . . ?
C13 N6 C10 N5 -178.5(2) . . . . ?
C10 N5 C11 C12 0.0(3) . . . . ?
Cu2 N5 C11 C12 -172.34(18) . . . . ?
N5 C11 C12 N6 -0.2(3) . . . . ?
C10 N6 C12 C11 0.4(3) . . . . ?
C13 N6 C12 C11 178.5(2) . . . . ?
C10 N6 C13 C14 106.2(3) . . . . ?
C12 N6 C13 C14 -71.5(3) . . . . ?
N6 C13 C14 C15 -86.6(3) . . . . ?
N6 C13 C14 C16 93.5(3) . . . . ?
C16 C14 C15 C16 -0.1(4) . . . 3_777 ?
C13 C14 C15 C16 -179.9(2) . . . 3_777 ?
C15 C14 C16 C15 0.1(4) . . . 3_777 ?
C13 C14 C16 C15 179.9(2) . . . 3_777 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 979081'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_gg

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 Cu N3'
_chemical_formula_sum            'C9 H9 Cu N3'
_chemical_formula_weight         222.73

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'
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   C2/c
_symmetry_space_group_name_Hall  '-C 2yc '

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

_cell_length_a                   15.7226(6)
_cell_length_b                   14.1888(6)
_cell_length_c                   9.1539(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.662(3)
_cell_angle_gamma                90.00
_cell_volume                     1999.94(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6466
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      24.99

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    2.139
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.6994
_exptl_absorpt_correction_T_max  0.7684
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13215
_diffrn_reflns_av_R_equivalents  0.1398
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.05
_reflns_number_total             1775
_reflns_number_gt                1477
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0596P)²+0.2790P] where P=(Fo²+2Fc²)/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         1775
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.1039
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.341081(18) 0.16194(2) 0.20397(3) 0.06774(19) Uani 1 1 d . . .
C1 C 0.46230(15) 0.1398(2) 0.2387(3) 0.0784(7) Uani 0.50 1 d P . .
N1 N 0.46230(15) 0.1398(2) 0.2387(3) 0.0784(7) Uani 0.50 1 d P . .
C2 C 0.27037(14) 0.22779(17) 0.0482(2) 0.0714(6) Uani 0.50 1 d P . .
N2 N 0.27037(14) 0.22779(17) 0.0482(2) 0.0714(6) Uani 0.50 1 d P . .
C3 C 0.3003(2) 0.06176(19) 0.6103(3) 0.0757(7) Uani 1 1 d . . .
H3 H 0.3190 0.0316 0.7013 0.091 Uiso 1 1 calc R . .
C4 C 0.34466(17) 0.07100(18) 0.5018(3) 0.0706(6) Uani 1 1 d . . .
H4 H 0.4004 0.0480 0.5048 0.085 Uiso 1 1 calc R . .
C5 C 0.22075(14) 0.13929(16) 0.4235(2) 0.0531(5) Uani 1 1 d . . .
C6 C 0.14675(16) 0.19058(19) 0.3347(3) 0.0666(6) Uani 1 1 d . . .
H6A H 0.1642 0.2199 0.2510 0.100 Uiso 1 1 calc R . .
H6B H 0.1276 0.2380 0.3955 0.100 Uiso 1 1 calc R . .
H6C H 0.1001 0.1473 0.2998 0.100 Uiso 1 1 calc R . .
C7 C 0.14936(17) 0.1097(2) 0.6415(3) 0.0792(8) Uani 1 1 d . . .
H7A H 0.1318 0.1749 0.6474 0.095 Uiso 1 1 calc R . .
H7B H 0.1691 0.0868 0.7425 0.095 Uiso 1 1 calc R . .
C8 C 0.07233(17) 0.05278(16) 0.5671(2) 0.0619(6) Uani 1 1 d . . .
C9 C 0.08223(18) -0.03738(17) 0.5142(3) 0.0660(6) Uani 1 1 d . . .
H9 H 0.1375 -0.0631 0.5232 0.079 Uiso 1 1 calc R . .
C10 C -0.01017(18) 0.08894(17) 0.5518(3) 0.0670(7) Uani 1 1 d . . .
H10 H -0.0176 0.1494 0.5866 0.080 Uiso 1 1 calc R . .
N3 N 0.29520(12) 0.12010(13) 0.38369(18) 0.0574(5) Uani 1 1 d . . .
N4 N 0.22161(13) 0.10517(14) 0.5623(2) 0.0631(5) 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 0.0658(3) 0.0705(3) 0.0683(3) 0.00082(13) 0.01684(19) -0.00572(13)
C1 0.0667(14) 0.0908(17) 0.0792(15) 0.0040(13) 0.0183(14) 0.0018(11)
N1 0.0667(14) 0.0908(17) 0.0792(15) 0.0040(13) 0.0183(14) 0.0018(11)
C2 0.0603(14) 0.0877(18) 0.0681(14) 0.0075(11) 0.0177(11) -0.0066(12)
N2 0.0603(14) 0.0877(18) 0.0681(14) 0.0075(11) 0.0177(11) -0.0066(12)
C3 0.090(2) 0.0698(17) 0.0618(15) 0.0156(12) 0.0027(13) -0.0059(14)
C4 0.0694(16) 0.0667(16) 0.0720(15) 0.0079(12) 0.0055(12) 0.0089(12)
C5 0.0576(14) 0.0502(12) 0.0516(11) -0.0051(9) 0.0112(10) -0.0087(10)
C6 0.0559(15) 0.0765(16) 0.0672(14) -0.0022(13) 0.0118(11) -0.0005(12)
C7 0.0952(19) 0.086(2) 0.0638(15) -0.0164(13) 0.0335(14) -0.0293(15)
C8 0.0816(17) 0.0613(14) 0.0500(12) -0.0047(10) 0.0308(11) -0.0183(12)
C9 0.0772(16) 0.0617(15) 0.0660(14) -0.0039(11) 0.0307(13) -0.0057(12)
C10 0.0946(19) 0.0518(13) 0.0631(14) -0.0081(10) 0.0360(13) -0.0126(12)
N3 0.0572(11) 0.0576(11) 0.0569(10) 0.0026(9) 0.0100(8) 0.0004(9)
N4 0.0727(13) 0.0635(13) 0.0549(10) -0.0003(9) 0.0172(9) -0.0174(10)

_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 C2 1.871(2) . ?
Cu1 C1 1.894(2) . ?
Cu1 N3 2.0148(17) . ?
C1 N1 1.162(5) 2_655 ?
C1 C1 1.162(5) 2_655 ?
C2 N2 1.165(4) 7 ?
C2 C2 1.165(4) 7 ?
C3 C4 1.330(4) . ?
C3 N4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 N3 1.385(3) . ?
C4 H4 0.9300 . ?
C5 N3 1.323(3) . ?
C5 N4 1.357(3) . ?
C5 C6 1.470(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 N4 1.468(3) . ?
C7 C8 1.500(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C10 1.375(3) . ?
C8 C9 1.388(3) . ?
C9 C10 1.381(3) 5_556 ?
C9 H9 0.9300 . ?
C10 C9 1.381(3) 5_556 ?
C10 H10 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
C2 Cu1 C1 129.30(11) . . ?
C2 Cu1 N3 120.92(9) . . ?
C1 Cu1 N3 109.16(9) . . ?
N1 C1 C1 0.0(3) 2_655 2_655 ?
N1 C1 Cu1 170.45(9) 2_655 . ?
C1 C1 Cu1 170.45(9) 2_655 . ?
N2 C2 C2 0.0(3) 7 7 ?
N2 C2 Cu1 176.5(3) 7 . ?
C2 C2 Cu1 176.5(3) 7 . ?
C4 C3 N4 107.0(2) . . ?
C4 C3 H3 126.5 . . ?
N4 C3 H3 126.5 . . ?
C3 C4 N3 109.6(2) . . ?
C3 C4 H4 125.2 . . ?
N3 C4 H4 125.2 . . ?
N3 C5 N4 110.0(2) . . ?
N3 C5 C6 126.5(2) . . ?
N4 C5 C6 123.4(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 C8 112.76(19) . . ?
N4 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N4 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C10 C8 C9 118.6(2) . . ?
C10 C8 C7 120.3(2) . . ?
C9 C8 C7 121.2(2) . . ?
C10 C9 C8 120.1(2) 5_556 . ?
C10 C9 H9 120.0 5_556 . ?
C8 C9 H9 120.0 . . ?
C8 C10 C9 121.4(2) . 5_556 ?
C8 C10 H10 119.3 . . ?
C9 C10 H10 119.3 5_556 . ?
C5 N3 C4 106.07(19) . . ?
C5 N3 Cu1 130.34(15) . . ?
C4 N3 Cu1 123.25(16) . . ?
C5 N4 C3 107.3(2) . . ?
C5 N4 C7 125.8(2) . . ?
C3 N4 C7 126.8(2) . . ?

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
C2 Cu1 C1 N1 61(2) . . . 2_655 ?
N3 Cu1 C1 N1 -109(2) . . . 2_655 ?
C2 Cu1 C1 C1 61(2) . . . 2_655 ?
N3 Cu1 C1 C1 -109(2) . . . 2_655 ?
C1 Cu1 C2 N2 -42(5) . . . 7 ?
N3 Cu1 C2 N2 128(5) . . . 7 ?
C1 Cu1 C2 C2 -42(5) . . . 7 ?
N3 Cu1 C2 C2 128(5) . . . 7 ?
N4 C3 C4 N3 0.0(3) . . . . ?
N4 C7 C8 C10 -136.6(2) . . . . ?
N4 C7 C8 C9 44.2(3) . . . . ?
C10 C8 C9 C10 -0.2(4) . . . 5_556 ?
C7 C8 C9 C10 179.0(2) . . . 5_556 ?
C9 C8 C10 C9 0.2(4) . . . 5_556 ?
C7 C8 C10 C9 -179.0(2) . . . 5_556 ?
N4 C5 N3 C4 0.6(2) . . . . ?
C6 C5 N3 C4 -180.0(2) . . . . ?
N4 C5 N3 Cu1 -172.70(14) . . . . ?
C6 C5 N3 Cu1 6.7(4) . . . . ?
C3 C4 N3 C5 -0.3(3) . . . . ?
C3 C4 N3 Cu1 173.55(17) . . . . ?
C2 Cu1 N3 C5 -7.9(2) . . . . ?
C1 Cu1 N3 C5 163.9(2) . . . . ?
C2 Cu1 N3 C4 179.82(19) . . . . ?
C1 Cu1 N3 C4 -8.4(2) . . . . ?
N3 C5 N4 C3 -0.6(3) . . . . ?
C6 C5 N4 C3 179.9(2) . . . . ?
N3 C5 N4 C7 -177.5(2) . . . . ?
C6 C5 N4 C7 3.0(4) . . . . ?
C4 C3 N4 C5 0.4(3) . . . . ?
C4 C3 N4 C7 177.2(2) . . . . ?
C8 C7 N4 C5 65.2(3) . . . . ?
C8 C7 N4 C3 -111.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 979082'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_gg

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 Cu N3'
_chemical_formula_sum            'C9 H9 Cu N3'
_chemical_formula_weight         222.73

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'
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   Fddd

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'

_cell_length_a                   13.868(3)
_cell_length_b                   22.973(4)
_cell_length_c                   24.215(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7715(2)
_cell_formula_units_Z            32
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2236
_cell_measurement_theta_min      5.16
_cell_measurement_theta_max      25.50

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3616
_exptl_absorpt_coefficient_mu    2.218
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.6411
_exptl_absorpt_correction_T_max  0.7614
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6519
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.81
_diffrn_reflns_theta_max         25.04
_reflns_number_total             1689
_reflns_number_gt                1282
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0669P)²+0.0600P] where P=(Fo²+2Fc²)/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         1689
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.003
_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
C1 C 0.1413(2) 1.10150(12) 0.35830(12) 0.0601(8) Uani 0.50 1 d P . .
N1 N 0.1413(2) 1.10150(12) 0.35830(12) 0.0601(8) Uani 0.50 1 d P . .
Cu1 Cu 0.20470(3) 1.028572(18) 0.349415(17) 0.0621(2) Uani 1 1 d . . .
N4 N 0.0808(2) 0.90654(12) 0.24605(11) 0.0569(7) Uani 1 1 d . . .
N3 N 0.1258(2) 0.97182(11) 0.30705(11) 0.0631(8) Uani 1 1 d . . .
C5 C 0.1497(2) 0.92574(14) 0.27928(14) 0.0566(8) Uani 1 1 d . . .
C7 C 0.0816(3) 0.85825(13) 0.20829(13) 0.0551(8) Uani 1 1 d . . .
H7A H 0.1478 0.8506 0.1974 0.066 Uiso 1 1 calc R . .
H7B H 0.0462 0.8692 0.1753 0.066 Uiso 1 1 calc R . .
C3 C 0.0303(3) 0.98379(16) 0.28919(17) 0.0662(10) Uani 1 1 d . . .
H3 H -0.0073 1.0147 0.3015 0.079 Uiso 1 1 calc R . .
C6 C 0.2451(3) 0.89530(19) 0.28483(17) 0.0783(11) Uani 1 1 d . . .
H6A H 0.2803 0.9117 0.3152 0.117 Uiso 1 1 calc R . .
H6B H 0.2815 0.9002 0.2514 0.117 Uiso 1 1 calc R . .
H6C H 0.2345 0.8546 0.2914 0.117 Uiso 1 1 calc R . .
C4 C 0.0032(3) 0.94509(17) 0.25295(16) 0.0681(10) Uani 1 1 d . . .
H4 H -0.0562 0.9434 0.2351 0.082 Uiso 1 1 calc R . .
C8 C 0.0388(2) 0.80283(12) 0.23103(12) 0.0454(7) Uani 1 1 d . . .
C9 C 0.0118(3) 0.75948(14) 0.19474(13) 0.0548(8) Uani 1 1 d . . .
H9 H 0.0191 0.7654 0.1570 0.066 Uiso 1 1 calc R . .
C10 C 0.0260(2) 0.79275(14) 0.28657(13) 0.0562(8) Uani 1 1 d . . .
H10 H 0.0430 0.8214 0.3119 0.067 Uiso 1 1 calc R . .
N2 N 0.3341(2) 1.01511(14) 0.37000(16) 0.0725(9) Uani 0.50 1 d P . .
C2 C 0.3341(2) 1.01511(14) 0.37000(16) 0.0725(9) Uani 0.50 1 d P . .

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
C1 0.0595(19) 0.0548(17) 0.0660(19) -0.0062(12) -0.0060(15) -0.0039(15)
N1 0.0595(19) 0.0548(17) 0.0660(19) -0.0062(12) -0.0060(15) -0.0039(15)
Cu1 0.0702(4) 0.0526(3) 0.0636(3) -0.00720(18) -0.0028(2) -0.01140(19)
N4 0.0720(18) 0.0433(15) 0.0555(16) -0.0063(12) -0.0004(14) -0.0060(13)
N3 0.074(2) 0.0473(16) 0.0676(18) -0.0108(13) -0.0017(15) -0.0014(14)
C5 0.066(2) 0.0462(18) 0.0576(19) 0.0003(15) 0.0003(16) -0.0036(15)
C7 0.072(2) 0.0404(17) 0.0530(19) -0.0038(13) -0.0073(15) -0.0041(15)
C3 0.058(2) 0.056(2) 0.085(3) -0.006(2) -0.0035(19) 0.0209(17)
C6 0.057(2) 0.083(3) 0.095(3) 0.007(2) -0.001(2) 0.029(2)
C4 0.053(2) 0.072(2) 0.079(2) 0.002(2) -0.0136(18) 0.0150(19)
C8 0.0537(18) 0.0361(15) 0.0465(17) -0.0027(13) -0.0096(13) 0.0056(13)
C9 0.076(2) 0.0483(18) 0.0402(16) -0.0048(13) -0.0055(15) -0.0057(16)
C10 0.079(2) 0.0414(17) 0.0477(18) -0.0121(14) -0.0062(16) -0.0092(16)
N2 0.076(2) 0.0507(18) 0.091(2) -0.0040(17) -0.013(2) 0.0003(15)
C2 0.076(2) 0.0507(18) 0.091(2) -0.0040(17) -0.013(2) 0.0003(15)

_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
C1 N1 1.170(6) 14_465 ?
C1 C1 1.170(6) 14_465 ?
C1 Cu1 1.905(3) . ?
Cu1 N2 1.887(3) . ?
Cu1 N3 1.987(3) . ?
N4 C5 1.326(4) . ?
N4 C4 1.404(4) . ?
N4 C7 1.438(4) . ?
N3 C5 1.297(4) . ?
N3 C3 1.421(4) . ?
C5 C6 1.502(5) . ?
C7 C8 1.509(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C3 C4 1.305(5) . ?
C3 H3 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C4 H4 0.9300 . ?
C8 C10 1.376(4) . ?
C8 C9 1.380(4) . ?
C9 C10 1.385(5) 21_565 ?
C9 H9 0.9300 . ?
C10 C9 1.385(5) 21_565 ?
C10 H10 0.9300 . ?
N2 C2 1.161(7) 3 ?
N2 N2 1.161(7) 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
N1 C1 C1 0.0(4) 14_465 14_465 ?
N1 C1 Cu1 171.8(3) 14_465 . ?
C1 C1 Cu1 171.8(3) 14_465 . ?
N2 Cu1 C1 123.60(13) . . ?
N2 Cu1 N3 123.50(13) . . ?
C1 Cu1 N3 112.41(13) . . ?
C5 N4 C4 105.7(3) . . ?
C5 N4 C7 129.6(3) . . ?
C4 N4 C7 124.7(3) . . ?
C5 N3 C3 103.8(3) . . ?
C5 N3 Cu1 131.5(3) . . ?
C3 N3 Cu1 122.9(2) . . ?
N3 C5 N4 113.7(3) . . ?
N3 C5 C6 124.0(3) . . ?
N4 C5 C6 122.3(3) . . ?
N4 C7 C8 114.5(3) . . ?
N4 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
N4 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C4 C3 N3 110.0(3) . . ?
C4 C3 H3 125.0 . . ?
N3 C3 H3 125.0 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C4 N4 106.8(3) . . ?
C3 C4 H4 126.6 . . ?
N4 C4 H4 126.6 . . ?
C10 C8 C9 117.8(3) . . ?
C10 C8 C7 123.3(3) . . ?
C9 C8 C7 118.9(3) . . ?
C8 C9 C10 121.3(3) . 21_565 ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 21_565 . ?
C8 C10 C9 120.9(3) . 21_565 ?
C8 C10 H10 119.5 . . ?
C9 C10 H10 119.5 21_565 . ?
C2 N2 N2 0.0(4) 3 3 ?
C2 N2 Cu1 170.0(2) 3 . ?
N2 N2 Cu1 170.0(2) 3 . ?

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 C1 Cu1 N2 75(2) 14_465 . . . ?
C1 C1 Cu1 N2 75(2) 14_465 . . . ?
N1 C1 Cu1 N3 -97(2) 14_465 . . . ?
C1 C1 Cu1 N3 -97(2) 14_465 . . . ?
N2 Cu1 N3 C5 -14.3(4) . . . . ?
C1 Cu1 N3 C5 158.0(3) . . . . ?
N2 Cu1 N3 C3 -176.4(3) . . . . ?
C1 Cu1 N3 C3 -4.2(3) . . . . ?
C3 N3 C5 N4 -0.4(4) . . . . ?
Cu1 N3 C5 N4 -165.1(2) . . . . ?
C3 N3 C5 C6 -178.7(3) . . . . ?
Cu1 N3 C5 C6 16.6(5) . . . . ?
C4 N4 C5 N3 0.4(4) . . . . ?
C7 N4 C5 N3 178.1(3) . . . . ?
C4 N4 C5 C6 178.7(3) . . . . ?
C7 N4 C5 C6 -3.5(5) . . . . ?
C5 N4 C7 C8 96.5(4) . . . . ?
C4 N4 C7 C8 -86.2(4) . . . . ?
C5 N3 C3 C4 0.3(4) . . . . ?
Cu1 N3 C3 C4 166.6(3) . . . . ?
N3 C3 C4 N4 -0.1(4) . . . . ?
C5 N4 C4 C3 -0.2(4) . . . . ?
C7 N4 C4 C3 -178.1(3) . . . . ?
N4 C7 C8 C10 -18.4(5) . . . . ?
N4 C7 C8 C9 162.3(3) . . . . ?
C10 C8 C9 C10 -0.6(6) . . . 21_565 ?
C7 C8 C9 C10 178.6(3) . . . 21_565 ?
C9 C8 C10 C9 0.6(5) . . . 21_565 ?
C7 C8 C10 C9 -178.6(3) . . . 21_565 ?
C1 Cu1 N2 C2 -37(3) . . . 3 ?
N3 Cu1 N2 C2 135(3) . . . 3 ?
C1 Cu1 N2 N2 -37(3) . . . 3 ?
N3 Cu1 N2 N2 135(3) . . . 3 ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 979083'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_gg

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 Cu3 N7'
_chemical_formula_sum            'C23 H18 Cu3 N7'
_chemical_formula_weight         583.06

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'
Cu Cu 0.3201 1.2651 '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
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.3383(9)
_cell_length_b                   9.7110(11)
_cell_length_c                   9.8336(12)
_cell_angle_alpha                61.160(7)
_cell_angle_beta                 73.893(9)
_cell_angle_gamma                74.296(8)
_cell_volume                     581.90(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2705
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      25.20

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    2.742
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.5838
_exptl_absorpt_correction_T_max  0.6101
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6695
_diffrn_reflns_av_R_equivalents  0.2500
_diffrn_reflns_av_sigmaI/netI    0.1639
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2025
_reflns_number_gt                1397
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1169P)²+0.0420P] where P=(Fo²+2Fc²)/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         2025
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.2293
_refine_ls_wR_factor_gt          0.1921
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 1.04387(11) 0.27611(7) 0.92030(9) 0.0676(4) Uani 1 1 d . . .
Cu2 Cu 1.5000 0.5000 1.0000 0.0883(5) Uani 1 2 d S . .
N2 N 1.3269(10) 0.4179(6) 0.9667(7) 0.0840(17) Uani 1 1 d . . .
C3 C 0.7934(9) 0.3533(6) 0.6890(9) 0.0661(17) Uani 1 1 d . . .
H3 H 0.7889 0.2461 0.7258 0.079 Uiso 1 1 calc R . .
C4 C 0.7255(9) 0.4704(7) 0.5612(10) 0.0715(18) Uani 1 1 d . . .
H4 H 0.6661 0.4620 0.4939 0.086 Uiso 1 1 calc R . .
C5 C 0.8458(8) 0.5665(6) 0.6673(7) 0.0566(14) Uani 1 1 d . . .
H5 H 0.8845 0.6394 0.6848 0.068 Uiso 1 1 calc R . .
C6 C 0.7072(9) 0.7689(6) 0.4285(7) 0.0619(15) Uani 1 1 d . . .
H6A H 0.7798 0.8409 0.4248 0.074 Uiso 1 1 calc R . .
H6B H 0.7418 0.7666 0.3269 0.074 Uiso 1 1 calc R . .
C7 C 0.4997(8) 0.8322(5) 0.4545(7) 0.0530(13) Uani 1 1 d . . .
C8 C 0.3791(10) 0.7836(7) 0.5985(8) 0.0730(19) Uani 1 1 d . . .
H8 H 0.4295 0.7015 0.6857 0.088 Uiso 1 1 calc R . .
C9 C 0.1915(11) 0.8483(7) 0.6206(7) 0.0690(18) Uani 1 1 d . . .
H9 H 0.1196 0.8157 0.7219 0.083 Uiso 1 1 calc R . .
C10 C 0.1042(8) 0.9657(5) 0.4896(6) 0.0525(14) Uani 1 1 d . . .
C11 C 0.2232(9) 1.0116(6) 0.3432(6) 0.0558(14) Uani 1 1 d . . .
H11 H 0.1707 1.0877 0.2546 0.067 Uiso 1 1 calc R . .
C12 C 0.4145(9) 0.9497(6) 0.3237(8) 0.0666(16) Uani 1 1 d . . .
H12 H 0.4890 0.9854 0.2234 0.080 Uiso 1 1 calc R . .
C1 C 1.0089(10) 0.0617(6) 0.9852(7) 0.0745(17) Uani 0.50 1 d P . .
N1 N 1.0089(10) 0.0617(6) 0.9852(7) 0.0745(17) Uani 0.50 1 d P . .
C2 C 1.2168(10) 0.3647(6) 0.9506(8) 0.0649(15) Uani 1 1 d . . .
N3 N 0.8709(7) 0.4120(5) 0.7594(6) 0.0608(13) Uani 1 1 d . . .
N4 N 0.7633(7) 0.6070(5) 0.5514(6) 0.0542(12) 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 0.0791(7) 0.0590(5) 0.0574(6) -0.0161(4) -0.0189(5) -0.0119(4)
Cu2 0.1204(13) 0.0831(8) 0.0628(9) -0.0113(6) -0.0253(8) -0.0497(8)
N2 0.105(5) 0.072(3) 0.064(4) -0.014(3) -0.020(3) -0.026(3)
C3 0.053(3) 0.045(2) 0.108(5) -0.038(3) -0.027(3) 0.003(2)
C4 0.053(3) 0.068(3) 0.109(5) -0.051(4) -0.026(3) 0.003(3)
C5 0.067(4) 0.050(2) 0.060(3) -0.024(2) -0.025(3) -0.005(2)
C6 0.064(4) 0.061(3) 0.050(3) -0.012(3) -0.023(3) -0.005(3)
C7 0.058(3) 0.044(2) 0.054(3) -0.019(2) -0.018(3) 0.000(2)
C8 0.071(4) 0.057(3) 0.058(4) -0.006(3) -0.020(3) 0.010(3)
C9 0.077(4) 0.061(3) 0.040(3) -0.007(3) -0.019(3) 0.011(3)
C10 0.069(4) 0.0301(19) 0.046(3) -0.011(2) -0.012(3) 0.001(2)
C11 0.070(4) 0.055(2) 0.041(3) -0.016(2) -0.034(3) 0.008(2)
C12 0.068(4) 0.058(3) 0.054(3) -0.016(3) -0.004(3) -0.005(3)
C1 0.094(4) 0.055(2) 0.071(4) -0.011(3) -0.036(3) -0.016(3)
N1 0.094(4) 0.055(2) 0.071(4) -0.011(3) -0.036(3) -0.016(3)
C2 0.072(4) 0.055(3) 0.063(4) -0.014(3) -0.022(3) -0.018(3)
N3 0.062(3) 0.0432(19) 0.074(3) -0.025(2) -0.009(3) -0.0081(19)
N4 0.051(3) 0.056(2) 0.057(3) -0.025(2) -0.025(2) 0.005(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 C2 1.867(7) . ?
Cu1 C1 1.930(5) . ?
Cu1 N3 2.012(5) . ?
Cu2 N2 1.841(8) . ?
Cu2 N2 1.841(8) 2_867 ?
N2 C2 1.149(10) . ?
C3 C4 1.335(10) . ?
C3 N3 1.379(8) . ?
C3 H3 0.9300 . ?
C4 N4 1.381(7) . ?
C4 H4 0.9300 . ?
C5 N4 1.281(7) . ?
C5 N3 1.318(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.480(8) . ?
C6 N4 1.481(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.377(9) . ?
C7 C12 1.411(7) . ?
C8 C9 1.355(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.419(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(8) . ?
C10 C10 1.493(11) 2_576 ?
C11 C12 1.369(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C1 N1 1.125(10) 2_757 ?
C1 C1 1.125(10) 2_757 ?

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
C2 Cu1 C1 134.7(2) . . ?
C2 Cu1 N3 120.7(2) . . ?
C1 Cu1 N3 103.8(2) . . ?
N2 Cu2 N2 180.000(2) . 2_867 ?
C2 N2 Cu2 178.0(7) . . ?
C4 C3 N3 111.2(5) . . ?
C4 C3 H3 124.4 . . ?
N3 C3 H3 124.4 . . ?
C3 C4 N4 104.3(6) . . ?
C3 C4 H4 127.8 . . ?
N4 C4 H4 127.8 . . ?
N4 C5 N3 113.8(5) . . ?
N4 C5 H5 123.1 . . ?
N3 C5 H5 123.1 . . ?
C7 C6 N4 113.8(5) . . ?
C7 C6 H6A 108.8 . . ?
N4 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
N4 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C12 116.2(5) . . ?
C8 C7 C6 124.9(5) . . ?
C12 C7 C6 118.9(5) . . ?
C9 C8 C7 123.9(5) . . ?
C9 C8 H8 118.1 . . ?
C7 C8 H8 118.1 . . ?
C8 C9 C10 120.2(6) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 116.2(5) . . ?
C11 C10 C10 122.7(5) . 2_576 ?
C9 C10 C10 121.2(6) . 2_576 ?
C12 C11 C10 122.9(4) . . ?
C12 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
C11 C12 C7 120.5(6) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
N1 C1 C1 0.0(7) 2_757 2_757 ?
N1 C1 Cu1 176.3(9) 2_757 . ?
C1 C1 Cu1 176.3(9) 2_757 . ?
N2 C2 Cu1 178.2(8) . . ?
C5 N3 C3 102.7(5) . . ?
C5 N3 Cu1 131.1(4) . . ?
C3 N3 Cu1 123.8(3) . . ?
C5 N4 C4 107.9(5) . . ?
C5 N4 C6 128.6(5) . . ?
C4 N4 C6 123.5(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
N2 Cu2 N2 C2 -87(100) 2_867 . . . ?
N3 C3 C4 N4 0.3(7) . . . . ?
N4 C6 C7 C8 23.8(8) . . . . ?
N4 C6 C7 C12 -155.3(5) . . . . ?
C12 C7 C8 C9 -4.0(10) . . . . ?
C6 C7 C8 C9 176.9(7) . . . . ?
C7 C8 C9 C10 4.6(11) . . . . ?
C8 C9 C10 C11 -2.2(9) . . . . ?
C8 C9 C10 C10 177.7(7) . . . 2_576 ?
C9 C10 C11 C12 -0.5(8) . . . . ?
C10 C10 C11 C12 179.6(6) 2_576 . . . ?
C10 C11 C12 C7 1.0(9) . . . . ?
C8 C7 C12 C11 1.1(9) . . . . ?
C6 C7 C12 C11 -179.7(6) . . . . ?
C2 Cu1 C1 N1 -114(13) . . . 2_757 ?
N3 Cu1 C1 N1 55(13) . . . 2_757 ?
C2 Cu1 C1 C1 -114(13) . . . 2_757 ?
N3 Cu1 C1 C1 55(13) . . . 2_757 ?
Cu2 N2 C2 Cu1 -135(19) . . . . ?
C1 Cu1 C2 N2 70(20) . . . . ?
N3 Cu1 C2 N2 -97(20) . . . . ?
N4 C5 N3 C3 0.0(7) . . . . ?
N4 C5 N3 Cu1 162.7(4) . . . . ?
C4 C3 N3 C5 -0.2(7) . . . . ?
C4 C3 N3 Cu1 -164.5(4) . . . . ?
C2 Cu1 N3 C5 -3.9(7) . . . . ?
C1 Cu1 N3 C5 -174.6(5) . . . . ?
C2 Cu1 N3 C3 155.6(5) . . . . ?
C1 Cu1 N3 C3 -15.1(6) . . . . ?
N3 C5 N4 C4 0.2(7) . . . . ?
N3 C5 N4 C6 177.9(5) . . . . ?
C3 C4 N4 C5 -0.3(7) . . . . ?
C3 C4 N4 C6 -178.2(6) . . . . ?
C7 C6 N4 C5 -102.0(7) . . . . ?
C7 C6 N4 C4 75.4(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.141
_database_code_depnum_ccdc_archive 'CCDC 979084'
