# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xh14bis
_database_code_depnum_ccdc_archive 'CCDC 1019230'
_audit_update_record             
;
2014-10-24 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Cu4 N10'
_chemical_formula_sum            'C12 H12 Cu4 N10'
_chemical_formula_weight         550.52

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   P2(1)/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                   15.368(10)
_cell_length_b                   8.370(6)
_cell_length_c                   13.710(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.697(12)
_cell_angle_gamma                90.00
_cell_volume                     1727(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2003
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      25.77
_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.117
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    4.878
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.384
_exptl_absorpt_correction_T_max  0.505
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'

_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            10469
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         28.76
_reflns_number_total             4506
_reflns_number_gt                2251
_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)+(0.0627P)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         4322
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
Cu3 Cu 0.36373(4) 0.04683(8) 0.62769(6) 0.0458(2) Uani 1 1 d . . .
Cu1 Cu 0.58237(5) 0.45032(8) 0.61548(6) 0.0496(2) Uani 1 1 d . . .
Cu2 Cu 1.08449(4) 0.77194(8) 0.62609(6) 0.0478(2) Uani 1 1 d . . .
Cu4 Cu 0.85698(4) 0.16779(8) 0.60298(6) 0.0502(2) Uani 1 1 d . . .
N1 N 1.0506(3) 0.5386(5) 0.6241(4) 0.0373(11) Uani 1 1 d . . .
N2 N 1.0991(3) 0.4067(5) 0.6134(3) 0.0338(10) Uani 1 1 d . . .
C4 C 0.9719(4) 0.4822(6) 0.6258(5) 0.0427(15) Uani 1 1 d . . .
H4 H 0.9243 0.5462 0.6338 0.051 Uiso 1 1 calc R . .
N3 N 0.9660(3) 0.3213(5) 0.6149(4) 0.0440(12) Uani 1 1 d . . .
N8 N 0.4210(3) 0.2454(6) 0.6224(4) 0.0566(15) Uani 1 1 d . . .
N7 N 0.5533(3) 0.6816(5) 0.6266(4) 0.0380(11) Uani 1 1 d . . .
N10 N 0.2590(3) -0.0652(6) 0.6284(4) 0.0522(14) Uani 1 1 d . . .
N5 N 0.7529(3) 0.2858(6) 0.6009(4) 0.0561(14) Uani 1 1 d . . .
C5 C 0.9716(4) 0.8740(6) 0.6206(5) 0.0395(14) Uani 1 1 d . . .
N6 N 0.6032(3) 0.8151(5) 0.6211(4) 0.0363(11) Uani 1 1 d . . .
N9 N 0.4696(3) -0.1040(5) 0.6225(4) 0.0467(13) Uani 1 1 d . . .
N4 N 0.9190(3) -0.0304(6) 0.6143(4) 0.0617(16) Uani 1 1 d . . .
C10 C 0.4733(4) 0.3423(6) 0.6195(5) 0.0433(15) Uani 1 1 d . . .
C3 C 1.0466(3) 0.2808(6) 0.6077(4) 0.0387(14) Uani 1 1 d . . .
H3 H 1.0647 0.1765 0.5995 0.046 Uiso 1 1 calc R . .
C9 C 0.4750(4) 0.7375(6) 0.6275(5) 0.0419(14) Uani 1 1 d . . .
H9 H 0.4267 0.6725 0.6313 0.050 Uiso 1 1 calc R . .
C1 C 1.2498(3) 0.4341(6) 0.7120(4) 0.0365(13) Uani 1 1 d . . .
H1A H 1.2307 0.5290 0.7424 0.044 Uiso 1 1 calc R . .
H1B H 1.3111 0.4501 0.7064 0.044 Uiso 1 1 calc R . .
C7 C 0.7549(3) 0.7918(6) 0.7203(4) 0.0358(13) Uani 1 1 d . . .
H7A H 0.8161 0.7779 0.7137 0.043 Uiso 1 1 calc R . .
H7B H 0.7376 0.6966 0.7520 0.043 Uiso 1 1 calc R . .
C6 C 0.6891(4) 0.3569(7) 0.6016(5) 0.0464(15) Uani 1 1 d . . .
C2 C 1.1940(3) 0.4145(7) 0.6103(4) 0.0411(14) Uani 1 1 d . . .
H2A H 1.2043 0.5038 0.5689 0.049 Uiso 1 1 calc R . .
H2B H 1.2112 0.3174 0.5805 0.049 Uiso 1 1 calc R . .
C11 C 0.5515(4) -0.0590(6) 0.6186(5) 0.0436(15) Uani 1 1 d . . .
H11 H 0.5698 0.0463 0.6146 0.052 Uiso 1 1 calc R . .
C8 C 0.6982(3) 0.8052(6) 0.6193(5) 0.0405(14) Uani 1 1 d . . .
H8A H 0.7154 0.8997 0.5868 0.049 Uiso 1 1 calc R . .
H8B H 0.7083 0.7131 0.5801 0.049 Uiso 1 1 calc R . .
C12 C 0.1938(4) -0.1346(6) 0.6283(5) 0.0442(15) 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
Cu3 0.0351(4) 0.0369(4) 0.0649(6) -0.0023(4) 0.0089(4) -0.0007(3)
Cu1 0.0431(4) 0.0304(4) 0.0762(6) -0.0051(4) 0.0143(4) 0.0039(3)
Cu2 0.0385(4) 0.0279(4) 0.0743(6) 0.0001(4) 0.0053(4) -0.0038(3)
Cu4 0.0370(4) 0.0320(4) 0.0817(7) 0.0042(4) 0.0126(4) 0.0030(3)
N1 0.029(2) 0.023(2) 0.057(3) 0.000(2) 0.002(2) 0.0003(18)
N2 0.033(2) 0.021(2) 0.046(3) -0.003(2) 0.005(2) 0.0012(17)
C4 0.035(3) 0.026(3) 0.064(5) 0.001(3) 0.005(3) 0.006(2)
N3 0.031(2) 0.027(2) 0.070(4) 0.002(2) 0.001(2) -0.0036(19)
N8 0.048(3) 0.047(3) 0.075(4) -0.003(3) 0.014(3) 0.011(3)
N7 0.031(2) 0.025(2) 0.058(3) 0.004(2) 0.008(2) -0.0017(18)
N10 0.040(3) 0.043(3) 0.074(4) -0.007(3) 0.015(3) 0.001(2)
N5 0.048(3) 0.043(3) 0.079(4) -0.004(3) 0.016(3) 0.003(3)
C5 0.033(3) 0.027(3) 0.057(4) 0.003(3) 0.008(3) 0.013(2)
N6 0.027(2) 0.027(2) 0.053(3) -0.001(2) 0.005(2) -0.0015(17)
N9 0.036(2) 0.026(2) 0.075(4) 0.002(2) 0.004(2) 0.003(2)
N4 0.057(3) 0.046(3) 0.085(5) 0.007(3) 0.021(3) -0.017(3)
C10 0.039(3) 0.028(3) 0.066(5) -0.004(3) 0.017(3) -0.005(2)
C3 0.032(3) 0.024(3) 0.057(4) -0.004(3) 0.002(3) -0.010(2)
C9 0.038(3) 0.023(3) 0.064(4) -0.001(3) 0.008(3) -0.002(2)
C1 0.024(2) 0.030(3) 0.054(4) -0.005(3) 0.002(3) 0.002(2)
C7 0.025(2) 0.029(3) 0.053(4) 0.003(3) 0.008(3) 0.000(2)
C6 0.041(3) 0.036(3) 0.060(4) -0.008(3) 0.007(3) 0.002(3)
C2 0.031(3) 0.039(3) 0.053(4) 0.001(3) 0.007(3) 0.003(2)
C11 0.037(3) 0.028(3) 0.062(4) 0.010(3) 0.000(3) -0.005(2)
C8 0.034(3) 0.032(3) 0.057(4) -0.003(3) 0.015(3) -0.004(2)
C12 0.046(3) 0.024(3) 0.062(5) -0.004(3) 0.010(3) -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
Cu3 N10 1.864(5) . ?
Cu3 N8 1.889(6) . ?
Cu3 N9 2.071(5) . ?
Cu1 C6 1.862(6) . ?
Cu1 C10 1.915(6) . ?
Cu1 N7 1.999(4) . ?
Cu2 C12 1.848(6) 1_665 ?
Cu2 C5 1.921(5) . ?
Cu2 N1 2.020(4) . ?
Cu4 N5 1.876(5) . ?
Cu4 N4 1.904(6) . ?
Cu4 N3 2.092(4) . ?
N1 C4 1.303(6) . ?
N1 N2 1.356(5) . ?
N2 C3 1.319(6) . ?
N2 C2 1.470(6) . ?
C4 N3 1.356(6) . ?
C4 H4 0.9300 . ?
N3 C3 1.307(6) . ?
N8 C10 1.149(7) . ?
N7 C9 1.294(6) . ?
N7 N6 1.366(5) . ?
N10 C12 1.158(7) . ?
N5 C6 1.148(7) . ?
C5 N4 1.129(7) 1_565 ?
N6 C11 1.316(7) 1_565 ?
N6 C8 1.467(6) . ?
N9 C11 1.326(7) . ?
N9 C9 1.330(6) 1_545 ?
N4 C5 1.129(7) 1_545 ?
C3 H3 0.9300 . ?
C9 N9 1.330(6) 1_565 ?
C9 H9 0.9300 . ?
C1 C2 1.491(8) . ?
C1 C7 1.520(8) 2_746 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C7 C8 1.484(8) . ?
C7 C1 1.520(8) 2_756 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C11 N6 1.316(7) 1_545 ?
C11 H11 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 Cu2 1.848(6) 1_445 ?

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
N10 Cu3 N8 148.4(2) . . ?
N10 Cu3 N9 112.2(2) . . ?
N8 Cu3 N9 99.18(19) . . ?
C6 Cu1 C10 126.8(2) . . ?
C6 Cu1 N7 129.0(2) . . ?
C10 Cu1 N7 104.2(2) . . ?
C12 Cu2 C5 128.5(2) 1_665 . ?
C12 Cu2 N1 129.8(2) 1_665 . ?
C5 Cu2 N1 101.6(2) . . ?
N5 Cu4 N4 150.6(2) . . ?
N5 Cu4 N3 110.2(2) . . ?
N4 Cu4 N3 98.55(19) . . ?
C4 N1 N2 103.9(4) . . ?
C4 N1 Cu2 126.0(4) . . ?
N2 N1 Cu2 130.0(3) . . ?
C3 N2 N1 108.3(4) . . ?
C3 N2 C2 129.2(4) . . ?
N1 N2 C2 122.5(4) . . ?
N1 C4 N3 113.5(5) . . ?
N1 C4 H4 123.3 . . ?
N3 C4 H4 123.3 . . ?
C3 N3 C4 102.9(4) . . ?
C3 N3 Cu4 126.3(4) . . ?
C4 N3 Cu4 130.8(4) . . ?
C10 N8 Cu3 163.3(5) . . ?
C9 N7 N6 103.8(4) . . ?
C9 N7 Cu1 125.0(4) . . ?
N6 N7 Cu1 130.7(3) . . ?
C12 N10 Cu3 179.7(6) . . ?
C6 N5 Cu4 178.6(6) . . ?
N4 C5 Cu2 161.0(5) 1_565 . ?
C11 N6 N7 108.3(4) 1_565 . ?
C11 N6 C8 129.9(4) 1_565 . ?
N7 N6 C8 121.7(4) . . ?
C11 N9 C9 103.6(5) . 1_545 ?
C11 N9 Cu3 126.0(4) . . ?
C9 N9 Cu3 130.4(4) 1_545 . ?
C5 N4 Cu4 164.4(5) 1_545 . ?
N8 C10 Cu1 163.2(5) . . ?
N3 C3 N2 111.4(5) . . ?
N3 C3 H3 124.3 . . ?
N2 C3 H3 124.3 . . ?
N7 C9 N9 114.2(5) . 1_565 ?
N7 C9 H9 122.9 . . ?
N9 C9 H9 122.9 1_565 . ?
C2 C1 C7 113.3(4) . 2_746 ?
C2 C1 H1A 108.9 . . ?
C7 C1 H1A 108.9 2_746 . ?
C2 C1 H1B 108.9 . . ?
C7 C1 H1B 108.9 2_746 . ?
H1A C1 H1B 107.7 . . ?
C8 C7 C1 114.8(4) . 2_756 ?
C8 C7 H7A 108.6 . . ?
C1 C7 H7A 108.6 2_756 . ?
C8 C7 H7B 108.6 . . ?
C1 C7 H7B 108.6 2_756 . ?
H7A C7 H7B 107.6 . . ?
N5 C6 Cu1 171.8(6) . . ?
N2 C2 C1 111.3(5) . . ?
N2 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N6 C11 N9 110.1(5) 1_545 . ?
N6 C11 H11 124.9 1_545 . ?
N9 C11 H11 124.9 . . ?
N6 C8 C7 112.7(4) . . ?
N6 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
N6 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N10 C12 Cu2 174.9(5) . 1_445 ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        28.76
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.825
_refine_diff_density_rms         0.128



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1019231'
_audit_update_record             
;
2014-10-24 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 Cu N4'
_chemical_formula_sum            'C6 H8 Cu N4'
_chemical_formula_weight         199.71

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'
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   Fdd2
_symmetry_space_group_name_Hall  'F 2 -2d'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   15.836(5)
_cell_length_b                   24.736(7)
_cell_length_c                   7.948(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3113.4(15)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3303
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      28.21

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    2.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.495
_exptl_absorpt_correction_T_max  0.628
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3956
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1378
_reflns_number_gt                1245
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0331P)²+4.2929P] 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       0.00099(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_number_reflns         1266
_refine_ls_number_parameters     102
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_ref         0.0611
_refine_ls_wR_factor_gt          0.0608
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.08483(2) 0.170173(14) 0.69009(5) 0.03291(16) Uani 1 1 d . . .
C2 C 0.0146(2) 0.42331(12) 0.4963(5) 0.0334(8) Uani 1 1 d . . .
H2A H -0.0302 0.4132 0.4194 0.040 Uiso 1 1 calc R . .
H2B H -0.0065 0.4191 0.6101 0.040 Uiso 1 1 calc R . .
C5 C 0.0042(2) 0.25598(12) 0.4752(4) 0.0295(8) Uani 1 1 d . . .
H5 H -0.0332 0.2293 0.4399 0.035 Uiso 1 1 calc R . .
N1 N 0.06610(16) 0.32956(9) 0.5013(3) 0.0251(6) Uani 1 1 d . . .
C6 C 0.18813(19) 0.14116(12) 0.7628(4) 0.0266(6) Uani 1 1 d . . .
N4 N 0.24789(15) 0.12074(11) 0.8135(4) 0.0327(6) Uani 1 1 d . . .
N3 N 0.06564(16) 0.24654(10) 0.5897(3) 0.0272(5) Uani 1 1 d . . .
C3 C 0.08851(16) 0.38615(12) 0.4711(4) 0.0291(7) Uani 1 1 d . . .
H3A H 0.1093 0.3900 0.3570 0.035 Uiso 1 1 calc R . .
H3B H 0.1336 0.3965 0.5472 0.035 Uiso 1 1 calc R . .
N2 N 0.00172(15) 0.30529(10) 0.4184(4) 0.0317(6) Uani 1 1 d . . .
C4 C 0.1036(2) 0.29384(12) 0.6016(4) 0.0284(6) Uani 1 1 d . . .
H4 H 0.1498 0.3012 0.6702 0.034 Uiso 1 1 calc R . .
C1 C 0.03737(19) 0.48128(12) 0.4677(6) 0.0399(8) Uani 1 1 d . . .
H1A H 0.0663 0.4844 0.3605 0.048 Uiso 1 1 calc R . .
H1B H 0.0764 0.4927 0.5548 0.048 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 0.0276(2) 0.0216(2) 0.0496(2) 0.00313(19) -0.01409(17) 0.00116(15)
C2 0.0303(15) 0.0210(16) 0.049(2) -0.0026(13) 0.0063(13) 0.0005(11)
C5 0.0305(13) 0.0169(14) 0.041(2) 0.0021(12) -0.0083(14) -0.0006(11)
N1 0.0260(11) 0.0145(13) 0.0347(14) 0.0010(9) -0.0024(11) 0.0002(9)
C6 0.0280(14) 0.0195(14) 0.0323(15) 0.0014(12) -0.0023(13) 0.0005(12)
N4 0.0294(13) 0.0270(14) 0.0416(15) 0.0045(12) -0.0044(13) 0.0023(10)
N3 0.0308(12) 0.0169(12) 0.0340(13) 0.0052(10) -0.0018(11) 0.0011(10)
C3 0.0325(15) 0.0140(14) 0.0409(19) 0.0024(12) 0.0012(13) -0.0006(11)
N2 0.0314(12) 0.0215(12) 0.0421(16) 0.0056(12) -0.0085(12) 0.0001(10)
C4 0.0302(14) 0.0216(16) 0.0335(16) 0.0047(13) -0.0046(13) 0.0004(12)
C1 0.0322(16) 0.0185(15) 0.069(2) 0.0007(16) -0.0028(16) 0.0016(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
Cu1 C6 1.878(3) . ?
Cu1 N4 1.983(3) 11_454 ?
Cu1 N3 2.073(3) . ?
Cu1 N2 2.354(3) 6 ?
C2 C1 1.496(4) . ?
C2 C3 1.501(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 N2 1.301(4) . ?
C5 N3 1.352(4) . ?
C5 H5 0.9300 . ?
N1 C4 1.330(4) . ?
N1 N2 1.354(4) . ?
N1 C3 1.464(4) . ?
C6 N4 1.146(4) . ?
N4 Cu1 1.983(3) 3 ?
N3 C4 1.319(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N2 Cu1 2.354(3) 6_554 ?
C4 H4 0.9300 . ?
C1 C1 1.503(6) 2_565 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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
C6 Cu1 N4 124.48(12) . 11_454 ?
C6 Cu1 N3 126.48(12) . . ?
N4 Cu1 N3 99.66(11) 11_454 . ?
C6 Cu1 N2 111.61(12) . 6 ?
N4 Cu1 N2 96.81(10) 11_454 6 ?
N3 Cu1 N2 88.66(10) . 6 ?
C1 C2 C3 112.3(3) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
N2 C5 N3 114.7(3) . . ?
N2 C5 H5 122.7 . . ?
N3 C5 H5 122.7 . . ?
C4 N1 N2 109.5(2) . . ?
C4 N1 C3 128.7(3) . . ?
N2 N1 C3 121.8(2) . . ?
N4 C6 Cu1 175.1(3) . . ?
C6 N4 Cu1 167.6(3) . 3 ?
C4 N3 C5 102.9(3) . . ?
C4 N3 Cu1 135.6(2) . . ?
C5 N3 Cu1 121.5(2) . . ?
N1 C3 C2 112.0(2) . . ?
N1 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
N1 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C5 N2 N1 102.9(2) . . ?
C5 N2 Cu1 121.8(2) . 6_554 ?
N1 N2 Cu1 134.35(19) . 6_554 ?
N3 C4 N1 110.0(3) . . ?
N3 C4 H4 125.0 . . ?
N1 C4 H4 125.0 . . ?
C2 C1 C1 113.7(3) . 2_565 ?
C2 C1 H1A 108.8 . . ?
C1 C1 H1A 108.8 2_565 . ?
C2 C1 H1B 108.8 . . ?
C1 C1 H1B 108.8 2_565 . ?
H1A C1 H1B 107.7 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.057


