# 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 2013


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#                                CCDC 
# 
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# 
#  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. 
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#  fide research purposes only. It may contain copyright material 
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data_bn1523
_database_code_depnum_ccdc_archive 'CCDC 893075'
#TrackingRef 'Bn1523.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H8 Cu N8'
_chemical_formula_weight         207.70

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

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                   17.665(4)
_cell_length_b                   6.3279(14)
_cell_length_c                   26.063(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.725(3)
_cell_angle_gamma                90.00
_cell_volume                     2862.4(11)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4455
_cell_measurement_theta_min      3.020
_cell_measurement_theta_max      29.124

_exptl_crystal_description       Chunk
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      -120
_exptl_crystal_density_diffrn    1.928
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1680
_exptl_absorpt_coefficient_mu    2.999
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.2943
_exptl_absorpt_correction_T_max  0.5557
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11765
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         29.12
_reflns_number_total             3768
_reflns_number_gt                3145
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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^)+(0.0516P)^2^+0.8150P] 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         3768
_refine_ls_number_parameters     212
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.997
_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 0.223105(15) 0.34641(4) 0.057981(11) 0.01446(9) Uani 1 1 d . . .
Cu2 Cu 0.293500(15) 0.64421(4) 0.170909(11) 0.01412(9) Uani 1 1 d . . .
N3 N 0.31280(12) 0.1822(3) 0.04343(8) 0.0196(4) Uani 1 1 d . A .
N4 N 0.37712(11) 0.2134(3) 0.06668(7) 0.0170(4) Uani 1 1 d . . .
N5 N 0.44009(12) 0.2381(4) 0.08871(9) 0.0272(5) Uani 1 1 d . A .
N6 N 0.27879(12) 0.6217(3) 0.06927(8) 0.0186(4) Uani 1 1 d . A .
N7 N 0.33291(11) 0.6662(3) 0.04994(7) 0.0150(4) Uani 1 1 d . . .
N8 N 0.38609(11) 0.7130(3) 0.03229(8) 0.0197(4) Uani 1 1 d . A .
N9 N 0.34827(11) 0.9231(3) 0.16644(8) 0.0180(4) Uani 1 1 d . A .
H9A H 0.3449 0.9610 0.1328 0.022 Uiso 1 1 calc R . .
H9B H 0.3262 1.0248 0.1828 0.022 Uiso 1 1 calc R . .
N10 N 0.40161(10) 0.5230(3) 0.18392(7) 0.0156(4) Uani 1 1 d . A .
H10A H 0.4138 0.4755 0.2170 0.019 Uiso 1 1 calc R . .
H10B H 0.4038 0.4133 0.1623 0.019 Uiso 1 1 calc R . .
N11 N 0.19028(11) 0.7829(3) 0.15966(8) 0.0173(4) Uani 1 1 d . A .
N12 N 0.14588(11) 0.7634(3) 0.18953(8) 0.0170(4) Uani 1 1 d . . .
N13 N 0.10154(13) 0.7499(4) 0.21645(9) 0.0287(5) Uani 1 1 d . A .
N14 N 0.25193(12) 0.3501(3) 0.16913(8) 0.0185(4) Uani 1 1 d . A .
N15 N 0.21720(11) 0.2867(3) 0.20128(7) 0.0159(4) Uani 1 1 d . . .
N16 N 0.18287(14) 0.2165(4) 0.23082(9) 0.0285(5) Uani 1 1 d . A .
N1 N 0.16302(11) 0.0821(3) 0.06596(7) 0.0149(4) Uani 0.802(6) 1 d PD A 1
H1A H 0.1716 -0.0154 0.0426 0.018 Uiso 0.802(6) 1 calc PR A 1
H1B H 0.1781 0.0282 0.0982 0.018 Uiso 0.802(6) 1 calc PR A 1
N2 N 0.12585(10) 0.4962(3) 0.06456(8) 0.0161(4) Uani 0.802(6) 1 d PD A 1
H2A H 0.1364 0.6046 0.0871 0.019 Uiso 0.802(6) 1 calc PR A 1
H2B H 0.1033 0.5485 0.0333 0.019 Uiso 0.802(6) 1 calc PR A 1
C1 C 0.08000(15) 0.1362(4) 0.05731(14) 0.0203(7) Uani 0.802(6) 1 d PD A 1
H1C H 0.0516 0.0279 0.0721 0.024 Uiso 0.802(6) 1 calc PR A 1
H1D H 0.0593 0.1468 0.0202 0.024 Uiso 0.802(6) 1 calc PR A 1
C2 C 0.07310(17) 0.3446(5) 0.08364(13) 0.0189(7) Uani 0.802(6) 1 d PD A 1
H2C H 0.0205 0.3955 0.0752 0.023 Uiso 0.802(6) 1 calc PR A 1
H2D H 0.0872 0.3290 0.1212 0.023 Uiso 0.802(6) 1 calc PR A 1
N1' N 0.16302(11) 0.0821(3) 0.06596(7) 0.0149(4) Uani 0.198(6) 1 d PD A 2
H1'1 H 0.1533 0.0113 0.0355 0.018 Uiso 0.198(6) 1 calc PR A 2
H1'2 H 0.1906 -0.0025 0.0902 0.018 Uiso 0.198(6) 1 calc PR A 2
N2' N 0.12585(10) 0.4962(3) 0.06456(8) 0.0161(4) Uani 0.198(6) 1 d PD A 2
H2'1 H 0.1296 0.5494 0.0970 0.019 Uiso 0.198(6) 1 calc PR A 2
H2'2 H 0.1172 0.6036 0.0416 0.019 Uiso 0.198(6) 1 calc PR A 2
C1' C 0.0895(4) 0.1410(9) 0.0819(4) 0.0203(7) Uani 0.198(6) 1 d PD A 2
H1'A H 0.0976 0.1626 0.1194 0.024 Uiso 0.198(6) 1 calc PR A 2
H1'B H 0.0517 0.0294 0.0727 0.024 Uiso 0.198(6) 1 calc PR A 2
C2' C 0.0615(3) 0.3414(8) 0.0539(4) 0.016(3) Uani 0.198(6) 1 d PD A 2
H2'A H 0.0471 0.3157 0.0166 0.019 Uiso 0.198(6) 1 calc PR A 2
H2'B H 0.0168 0.3952 0.0664 0.019 Uiso 0.198(6) 1 calc PR A 2
C3 C 0.43031(14) 0.8979(4) 0.19161(10) 0.0206(5) Uani 1 1 d . . .
H3A H 0.4355 0.9031 0.2293 0.025 Uiso 1 1 calc R A .
H3B H 0.4610 1.0109 0.1808 0.025 Uiso 1 1 calc R . .
C4 C 0.45745(13) 0.6873(4) 0.17507(10) 0.0197(5) Uani 1 1 d . A .
H4A H 0.4612 0.6914 0.1384 0.024 Uiso 1 1 calc R . .
H4B H 0.5080 0.6550 0.1952 0.024 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 0.01236(14) 0.01120(14) 0.02089(16) -0.00077(11) 0.00588(11) -0.00132(10)
Cu2 0.01331(14) 0.01120(14) 0.01852(16) -0.00003(10) 0.00473(11) -0.00122(10)
N3 0.0173(10) 0.0181(10) 0.0247(11) -0.0038(8) 0.0068(8) 0.0005(8)
N4 0.0208(10) 0.0143(9) 0.0176(9) 0.0020(8) 0.0078(8) 0.0051(8)
N5 0.0215(11) 0.0287(13) 0.0303(12) 0.0019(10) 0.0014(9) 0.0057(9)
N6 0.0193(10) 0.0145(9) 0.0244(10) -0.0049(8) 0.0104(8) -0.0081(8)
N7 0.0173(10) 0.0122(9) 0.0144(9) -0.0003(7) -0.0001(7) -0.0007(7)
N8 0.0179(10) 0.0198(10) 0.0222(10) 0.0020(9) 0.0060(8) -0.0032(8)
N9 0.0159(10) 0.0132(9) 0.0252(10) 0.0012(8) 0.0048(8) -0.0018(7)
N10 0.0170(9) 0.0133(9) 0.0170(9) 0.0002(7) 0.0047(7) -0.0003(7)
N11 0.0153(9) 0.0204(10) 0.0176(9) 0.0024(8) 0.0072(8) 0.0021(8)
N12 0.0180(10) 0.0142(9) 0.0183(9) -0.0037(8) 0.0018(8) -0.0016(8)
N13 0.0279(12) 0.0297(13) 0.0339(12) -0.0053(10) 0.0200(10) -0.0046(10)
N14 0.0213(10) 0.0145(10) 0.0215(10) -0.0031(8) 0.0084(8) -0.0065(8)
N15 0.0189(10) 0.0096(8) 0.0185(9) -0.0019(8) 0.0019(8) -0.0006(7)
N16 0.0409(14) 0.0223(11) 0.0256(11) -0.0025(10) 0.0148(10) -0.0079(10)
N1 0.0178(9) 0.0108(9) 0.0165(9) -0.0004(7) 0.0045(7) -0.0025(7)
N2 0.0131(9) 0.0143(9) 0.0216(10) -0.0003(8) 0.0053(7) -0.0016(7)
C1 0.0141(13) 0.0214(14) 0.0250(19) 0.0026(14) 0.0026(13) -0.0054(11)
C2 0.0159(14) 0.0218(16) 0.0203(16) -0.0015(13) 0.0068(13) -0.0034(12)
N1' 0.0178(9) 0.0108(9) 0.0165(9) -0.0004(7) 0.0045(7) -0.0025(7)
N2' 0.0131(9) 0.0143(9) 0.0216(10) -0.0003(8) 0.0053(7) -0.0016(7)
C1' 0.0141(13) 0.0214(14) 0.0250(19) 0.0026(14) 0.0026(13) -0.0054(11)
C2' 0.012(5) 0.017(6) 0.020(7) -0.005(5) 0.010(5) -0.009(4)
C3 0.0167(11) 0.0172(12) 0.0270(13) -0.0006(10) 0.0012(9) -0.0033(9)
C4 0.0144(11) 0.0220(12) 0.0230(12) 0.0036(10) 0.0043(9) -0.0020(9)

_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 N3 1.990(2) . ?
Cu1 N6 1.9954(19) . ?
Cu1 N2 1.9973(19) . ?
Cu1 N1 2.0122(19) . ?
Cu1 N14 2.847(2) . ?
Cu2 N11 1.995(2) . ?
Cu2 N14 1.998(2) . ?
Cu2 N9 2.027(2) . ?
Cu2 N10 2.0271(19) . ?
Cu2 N6 2.617(2) . ?
N3 N4 1.200(3) . ?
N4 N5 1.163(3) . ?
N6 N7 1.194(3) . ?
N7 N8 1.159(3) . ?
N9 C3 1.484(3) . ?
N9 H9A 0.9000 . ?
N9 H9B 0.9000 . ?
N10 C4 1.480(3) . ?
N10 H10A 0.9000 . ?
N10 H10B 0.9000 . ?
N11 N12 1.210(3) . ?
N12 N13 1.148(3) . ?
N14 N15 1.196(3) . ?
N15 N16 1.154(3) . ?
N1 C1 1.482(3) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N2 C2 1.486(3) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
C1 C2 1.502(4) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C1' C2' 1.501(5) . ?
C1' H1'A 0.9700 . ?
C1' H1'B 0.9700 . ?
C2' H2'A 0.9700 . ?
C2' H2'B 0.9700 . ?
C3 C4 1.506(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 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
N3 Cu1 N6 95.51(9) . . ?
N3 Cu1 N2 173.01(8) . . ?
N6 Cu1 N2 88.93(8) . . ?
N3 Cu1 N1 92.27(8) . . ?
N6 Cu1 N1 164.90(8) . . ?
N2 Cu1 N1 84.65(8) . . ?
N3 Cu1 N14 101.55(8) . . ?
N6 Cu1 N14 81.54(7) . . ?
N2 Cu1 N14 84.41(7) . . ?
N1 Cu1 N14 84.23(7) . . ?
N11 Cu2 N14 94.85(9) . . ?
N11 Cu2 N9 92.37(8) . . ?
N14 Cu2 N9 170.83(8) . . ?
N11 Cu2 N10 176.03(8) . . ?
N14 Cu2 N10 88.98(8) . . ?
N9 Cu2 N10 83.92(8) . . ?
N11 Cu2 N6 87.66(7) . . ?
N14 Cu2 N6 87.65(7) . . ?
N9 Cu2 N6 87.00(7) . . ?
N10 Cu2 N6 93.54(7) . . ?
N4 N3 Cu1 122.02(17) . . ?
N5 N4 N3 178.0(3) . . ?
N7 N6 Cu1 123.71(16) . . ?
N7 N6 Cu2 118.53(16) . . ?
Cu1 N6 Cu2 98.63(8) . . ?
N8 N7 N6 178.2(2) . . ?
C3 N9 Cu2 108.55(14) . . ?
C3 N9 H9A 110.0 . . ?
Cu2 N9 H9A 110.0 . . ?
C3 N9 H9B 110.0 . . ?
Cu2 N9 H9B 110.0 . . ?
H9A N9 H9B 108.4 . . ?
C4 N10 Cu2 110.04(14) . . ?
C4 N10 H10A 109.7 . . ?
Cu2 N10 H10A 109.7 . . ?
C4 N10 H10B 109.7 . . ?
Cu2 N10 H10B 109.7 . . ?
H10A N10 H10B 108.2 . . ?
N12 N11 Cu2 123.00(16) . . ?
N13 N12 N11 177.1(3) . . ?
N15 N14 Cu2 122.01(16) . . ?
N15 N14 Cu1 133.82(16) . . ?
Cu2 N14 Cu1 91.52(7) . . ?
N16 N15 N14 176.6(2) . . ?
C1 N1 Cu1 108.58(15) . . ?
C1 N1 H1A 110.0 . . ?
Cu1 N1 H1A 110.0 . . ?
C1 N1 H1B 110.0 . . ?
Cu1 N1 H1B 110.0 . . ?
H1A N1 H1B 108.4 . . ?
C2 N2 Cu1 108.98(16) . . ?
C2 N2 H2A 109.9 . . ?
Cu1 N2 H2A 109.9 . . ?
C2 N2 H2B 109.9 . . ?
Cu1 N2 H2B 109.9 . . ?
H2A N2 H2B 108.3 . . ?
N1 C1 C2 107.2(2) . . ?
N1 C1 H1C 110.3 . . ?
C2 C1 H1C 110.3 . . ?
N1 C1 H1D 110.3 . . ?
C2 C1 H1D 110.3 . . ?
H1C C1 H1D 108.5 . . ?
N2 C2 C1 107.7(2) . . ?
N2 C2 H2C 110.2 . . ?
C1 C2 H2C 110.2 . . ?
N2 C2 H2D 110.2 . . ?
C1 C2 H2D 110.2 . . ?
H2C C2 H2D 108.5 . . ?
C2' C1' H1'A 110.2 . . ?
C2' C1' H1'B 110.2 . . ?
H1'A C1' H1'B 108.5 . . ?
C1' C2' H2'A 110.3 . . ?
C1' C2' H2'B 110.3 . . ?
H2'A C2' H2'B 108.5 . . ?
N9 C3 C4 107.79(19) . . ?
N9 C3 H3A 110.1 . . ?
C4 C3 H3A 110.1 . . ?
N9 C3 H3B 110.1 . . ?
C4 C3 H3B 110.1 . . ?
H3A C3 H3B 108.5 . . ?
N10 C4 C3 108.65(19) . . ?
N10 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
N10 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.3 . . ?

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
N6 Cu1 N3 N4 38.2(2) . . . . ?
N2 Cu1 N3 N4 167.4(6) . . . . ?
N1 Cu1 N3 N4 -128.9(2) . . . . ?
N14 Cu1 N3 N4 -44.3(2) . . . . ?
Cu1 N3 N4 N5 163(8) . . . . ?
N3 Cu1 N6 N7 26.8(2) . . . . ?
N2 Cu1 N6 N7 -147.8(2) . . . . ?
N1 Cu1 N6 N7 147.5(3) . . . . ?
N14 Cu1 N6 N7 127.7(2) . . . . ?
N3 Cu1 N6 Cu2 -106.19(8) . . . . ?
N2 Cu1 N6 Cu2 79.22(8) . . . . ?
N1 Cu1 N6 Cu2 14.5(4) . . . . ?
N14 Cu1 N6 Cu2 -5.29(6) . . . . ?
N11 Cu2 N6 N7 136.34(18) . . . . ?
N14 Cu2 N6 N7 -128.70(18) . . . . ?
N9 Cu2 N6 N7 43.84(18) . . . . ?
N10 Cu2 N6 N7 -39.87(18) . . . . ?
N11 Cu2 N6 Cu1 -87.48(9) . . . . ?
N14 Cu2 N6 Cu1 7.47(8) . . . . ?
N9 Cu2 N6 Cu1 -179.98(9) . . . . ?
N10 Cu2 N6 Cu1 96.30(9) . . . . ?
Cu1 N6 N7 N8 -154(8) . . . . ?
Cu2 N6 N7 N8 -29(8) . . . . ?
N11 Cu2 N9 C3 159.91(15) . . . . ?
N14 Cu2 N9 C3 -58.1(6) . . . . ?
N10 Cu2 N9 C3 -18.66(15) . . . . ?
N6 Cu2 N9 C3 -112.55(15) . . . . ?
N11 Cu2 N10 C4 -29.8(12) . . . . ?
N14 Cu2 N10 C4 165.44(15) . . . . ?
N9 Cu2 N10 C4 -8.74(15) . . . . ?
N6 Cu2 N10 C4 77.85(15) . . . . ?
N14 Cu2 N11 N12 61.0(2) . . . . ?
N9 Cu2 N11 N12 -124.7(2) . . . . ?
N10 Cu2 N11 N12 -103.8(11) . . . . ?
N6 Cu2 N11 N12 148.4(2) . . . . ?
Cu2 N11 N12 N13 -176(100) . . . . ?
N11 Cu2 N14 N15 -64.2(2) . . . . ?
N9 Cu2 N14 N15 154.0(5) . . . . ?
N10 Cu2 N14 N15 114.8(2) . . . . ?
N6 Cu2 N14 N15 -151.6(2) . . . . ?
N11 Cu2 N14 Cu1 82.28(7) . . . . ?
N9 Cu2 N14 Cu1 -59.5(5) . . . . ?
N10 Cu2 N14 Cu1 -98.76(7) . . . . ?
N6 Cu2 N14 Cu1 -5.17(6) . . . . ?
N3 Cu1 N14 N15 -119.7(2) . . . . ?
N6 Cu1 N14 N15 146.4(2) . . . . ?
N2 Cu1 N14 N15 56.6(2) . . . . ?
N1 Cu1 N14 N15 -28.6(2) . . . . ?
N3 Cu1 N14 Cu2 100.80(9) . . . . ?
N6 Cu1 N14 Cu2 6.86(8) . . . . ?
N2 Cu1 N14 Cu2 -82.89(8) . . . . ?
N1 Cu1 N14 Cu2 -168.06(8) . . . . ?
Cu2 N14 N15 N16 173(4) . . . . ?
Cu1 N14 N15 N16 43(4) . . . . ?
N3 Cu1 N1 C1 -158.26(18) . . . . ?
N6 Cu1 N1 C1 80.7(4) . . . . ?
N2 Cu1 N1 C1 15.45(17) . . . . ?
N14 Cu1 N1 C1 100.35(17) . . . . ?
N3 Cu1 N2 C2 77.4(7) . . . . ?
N6 Cu1 N2 C2 -153.08(18) . . . . ?
N1 Cu1 N2 C2 13.23(17) . . . . ?
N14 Cu1 N2 C2 -71.47(17) . . . . ?
Cu1 N1 C1 C2 -40.6(3) . . . . ?
Cu1 N2 C2 C1 -39.1(3) . . . . ?
N1 C1 C2 N2 52.5(3) . . . . ?
Cu2 N9 C3 C4 42.0(2) . . . . ?
Cu2 N10 C4 C3 34.2(2) . . . . ?
N9 C3 C4 N10 -50.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        29.12
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         1.408
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.092


data_bn1524
_database_code_depnum_ccdc_archive 'CCDC 893076'
#TrackingRef 'Bn1524.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H16 Co N11 O3'
_chemical_formula_weight         325.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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

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                   13.671(4)
_cell_length_b                   9.447(2)
_cell_length_c                   9.343(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.349(3)
_cell_angle_gamma                90.00
_cell_volume                     1187.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2312
_cell_measurement_theta_min      2.635
_cell_measurement_theta_max      31.000

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    1.476
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.6004
_exptl_absorpt_correction_T_max  0.6734
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5540
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         31.00
_reflns_number_total             1868
_reflns_number_gt                1688
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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^)+(0.0485P)^2^+0.1600P] 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         1868
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
Co1 Co 0.5000 0.19896(2) 0.7500 0.01117(9) Uani 1 2 d S . .
N1 N 0.58601(9) 0.34171(12) 0.68604(12) 0.0127(2) Uani 1 1 d . . .
N2 N 0.59281(10) 0.05994(12) 0.69193(13) 0.0160(2) Uani 1 1 d . . .
N3 N 0.42198(10) 0.18726(12) 0.55315(13) 0.0166(2) Uani 1 1 d . . .
N4 N 0.37423(10) 0.28873(12) 0.50286(13) 0.0163(2) Uani 1 1 d . . .
N5 N 0.32660(10) 0.38256(14) 0.45027(14) 0.0250(3) Uani 1 1 d . . .
N6 N 0.5000 0.67041(18) 0.7500 0.0169(3) Uani 1 2 d S . .
O1 O 0.44577(8) 0.60311(11) 0.64952(10) 0.0223(2) Uani 1 1 d . . .
O2 O 0.5000 0.80175(14) 0.7500 0.0322(5) Uani 1 2 d S . .
C1 C 0.68236(11) 0.27696(15) 0.67131(16) 0.0171(3) Uani 1 1 d . . .
H1A H 0.7260 0.2684 0.7677 0.021 Uiso 1 1 calc R . .
H1B H 0.7166 0.3356 0.6077 0.021 Uiso 1 1 calc R . .
C2 C 0.65862(11) 0.13217(15) 0.60481(16) 0.0185(3) Uani 1 1 d . . .
H2A H 0.6247 0.1414 0.5023 0.022 Uiso 1 1 calc R . .
H2B H 0.7205 0.0771 0.6072 0.022 Uiso 1 1 calc R . .
H01A H 0.5961(16) 0.421(2) 0.743(2) 0.034(5) Uiso 1 1 d . . .
H01B H 0.5585(13) 0.372(2) 0.601(2) 0.032(5) Uiso 1 1 d . . .
H02A H 0.6288(14) 0.035(2) 0.769(2) 0.023(5) Uiso 1 1 d . . .
H02B H 0.5655(14) -0.017(2) 0.645(2) 0.029(5) Uiso 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
Co1 0.01344(15) 0.00966(13) 0.01136(14) 0.000 0.00476(10) 0.000
N1 0.0139(5) 0.0114(5) 0.0134(5) 0.0018(4) 0.0039(4) -0.0004(4)
N2 0.0203(6) 0.0116(5) 0.0179(6) 0.0015(4) 0.0081(5) 0.0028(4)
N3 0.0180(6) 0.0189(5) 0.0128(5) -0.0037(4) 0.0022(4) -0.0006(4)
N4 0.0168(6) 0.0200(5) 0.0119(5) -0.0033(4) 0.0022(4) -0.0061(4)
N5 0.0258(7) 0.0211(6) 0.0252(7) 0.0018(5) -0.0031(5) -0.0016(5)
N6 0.0245(9) 0.0127(7) 0.0156(7) 0.000 0.0089(7) 0.000
O1 0.0281(6) 0.0203(5) 0.0168(5) 0.0027(4) -0.0004(4) -0.0030(4)
O2 0.0668(14) 0.0095(7) 0.0242(8) 0.000 0.0186(9) 0.000
C1 0.0135(6) 0.0188(6) 0.0203(7) 0.0028(5) 0.0063(5) 0.0012(5)
C2 0.0206(7) 0.0177(6) 0.0202(6) 0.0011(5) 0.0115(5) 0.0034(5)

_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
Co1 N1 1.9521(11) . ?
Co1 N1 1.9521(11) 2_656 ?
Co1 N3 1.9564(13) 2_656 ?
Co1 N3 1.9564(13) . ?
Co1 N2 1.9688(12) 2_656 ?
Co1 N2 1.9688(12) . ?
N1 C1 1.4810(18) . ?
N1 H01A 0.91(2) . ?
N1 H01B 0.87(2) . ?
N2 C2 1.4834(17) . ?
N2 H02A 0.83(2) . ?
N2 H02B 0.89(2) . ?
N3 N4 1.2065(17) . ?
N4 N5 1.1559(18) . ?
N6 O2 1.241(2) . ?
N6 O1 1.2590(13) 2_656 ?
N6 O1 1.2590(13) . ?
C1 C2 1.513(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?

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 Co1 N1 92.61(7) . 2_656 ?
N1 Co1 N3 94.02(5) . 2_656 ?
N1 Co1 N3 90.45(5) 2_656 2_656 ?
N1 Co1 N3 90.45(5) . . ?
N1 Co1 N3 94.02(5) 2_656 . ?
N3 Co1 N3 173.52(7) 2_656 . ?
N1 Co1 N2 176.96(5) . 2_656 ?
N1 Co1 N2 85.58(5) 2_656 2_656 ?
N3 Co1 N2 88.44(5) 2_656 2_656 ?
N3 Co1 N2 87.24(5) . 2_656 ?
N1 Co1 N2 85.58(5) . . ?
N1 Co1 N2 176.96(5) 2_656 . ?
N3 Co1 N2 87.24(5) 2_656 . ?
N3 Co1 N2 88.44(5) . . ?
N2 Co1 N2 96.32(7) 2_656 . ?
C1 N1 Co1 109.75(8) . . ?
C1 N1 H01A 110.3(13) . . ?
Co1 N1 H01A 115.0(13) . . ?
C1 N1 H01B 107.4(13) . . ?
Co1 N1 H01B 109.0(13) . . ?
H01A N1 H01B 104.9(18) . . ?
C2 N2 Co1 109.20(8) . . ?
C2 N2 H02A 106.6(13) . . ?
Co1 N2 H02A 105.0(13) . . ?
C2 N2 H02B 110.3(13) . . ?
Co1 N2 H02B 116.3(12) . . ?
H02A N2 H02B 108.9(19) . . ?
N4 N3 Co1 119.12(9) . . ?
N5 N4 N3 177.28(15) . . ?
O2 N6 O1 120.33(8) . 2_656 ?
O2 N6 O1 120.33(8) . . ?
O1 N6 O1 119.34(16) 2_656 . ?
N1 C1 C2 106.42(11) . . ?
N1 C1 H1A 110.4 . . ?
C2 C1 H1A 110.4 . . ?
N1 C1 H1B 110.4 . . ?
C2 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
N2 C2 C1 107.28(11) . . ?
N2 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
N2 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.5 . . ?

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 Co1 N1 C1 161.78(11) 2_656 . . . ?
N3 Co1 N1 C1 71.14(9) 2_656 . . . ?
N3 Co1 N1 C1 -104.17(9) . . . . ?
N2 Co1 N1 C1 -144.8(8) 2_656 . . . ?
N2 Co1 N1 C1 -15.77(9) . . . . ?
N1 Co1 N2 C2 -12.74(10) . . . . ?
N1 Co1 N2 C2 -66.3(9) 2_656 . . . ?
N3 Co1 N2 C2 -106.99(10) 2_656 . . . ?
N3 Co1 N2 C2 77.84(10) . . . . ?
N2 Co1 N2 C2 164.89(12) 2_656 . . . ?
N1 Co1 N3 N4 -65.78(12) . . . . ?
N1 Co1 N3 N4 26.87(12) 2_656 . . . ?
N3 Co1 N3 N4 160.48(11) 2_656 . . . ?
N2 Co1 N3 N4 112.24(12) 2_656 . . . ?
N2 Co1 N3 N4 -151.35(12) . . . . ?
Co1 N3 N4 N5 -168(3) . . . . ?
Co1 N1 C1 C2 40.07(13) . . . . ?
Co1 N2 C2 C1 37.81(14) . . . . ?
N1 C1 C2 N2 -50.53(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        31.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.088