# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_m+p21n

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H28 Cu3 N8 O16, C2 H10 N2, 4(H2 O)'
_chemical_formula_sum            'C34 H46 Cu3 N10 O20'
_chemical_formula_weight         1105.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '
_symmetry_space_group_name_Hall  '-P 2yn '

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

_cell_length_a                   8.152(2)
_cell_length_b                   20.538(5)
_cell_length_c                   12.736(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.44(2)
_cell_angle_gamma                90.00
_cell_volume                     2128.5(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8052
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      32.45

_exptl_crystal_description       irregular
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1134
_exptl_absorpt_coefficient_mu    1.579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5825
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            35349
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         35.17
_reflns_number_total             9453
_reflns_number_gt                6734
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XPW (Siemens, 1996)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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 > 2σ(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)+(0.0528P)²+0.1097P] 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         9453
_refine_ls_number_parameters     336
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.1002
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.021
_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
Cu1 Cu 0.41369(2) 0.734887(8) 0.553105(12) 0.02551(5) Uani 1 1 d . . .
N1 N 0.38865(14) 0.73453(5) 0.39949(8) 0.02225(19) Uani 1 1 d . . .
O5 O 0.26265(15) 0.81147(5) 0.60629(9) 0.0362(2) Uani 1 1 d . . .
O3 O 0.58419(15) 0.81797(6) 0.50570(8) 0.0368(2) Uani 1 1 d . . .
N2 N 0.44168(14) 0.72476(5) 0.70320(8) 0.02212(19) Uani 1 1 d . . .
C2 C 0.29612(16) 0.68844(6) 0.35084(10) 0.0236(2) Uani 1 1 d . . .
C6 C 0.46747(16) 0.77861(6) 0.34388(10) 0.0233(2) Uani 1 1 d . . .
C9 C 0.36906(16) 0.76619(6) 0.76552(10) 0.0229(2) Uani 1 1 d . . .
O1 O 0.21166(16) 0.65984(5) 0.51771(8) 0.0374(3) Uani 1 1 d . . .
O2 O 0.15002(16) 0.59160(5) 0.38441(9) 0.0401(3) Uani 1 1 d . . .
C13 C 0.53495(16) 0.67598(6) 0.74101(10) 0.0240(2) Uani 1 1 d . . .
C10 C 0.38875(18) 0.75991(7) 0.87363(11) 0.0302(3) Uani 1 1 d . . .
H10 H 0.3384 0.7889 0.9177 0.036 Uiso 1 1 calc R . .
O7 O 0.58610(16) 0.65866(6) 0.56406(8) 0.0401(3) Uani 1 1 d . . .
O6 O 0.21260(16) 0.86312(6) 0.75532(11) 0.0468(3) Uani 1 1 d . . .
C3 C 0.27609(18) 0.68619(7) 0.24224(10) 0.0270(2) Uani 1 1 d . . .
H3 H 0.2112 0.6542 0.2089 0.032 Uiso 1 1 calc R . .
C1 C 0.21182(18) 0.64213(6) 0.42338(11) 0.0277(3) Uani 1 1 d . . .
O4 O 0.62267(16) 0.87514(5) 0.36029(9) 0.0413(3) Uani 1 1 d . . .
C5 C 0.45307(18) 0.77855(7) 0.23509(10) 0.0276(3) Uani 1 1 d . . .
H5 H 0.5090 0.8091 0.1969 0.033 Uiso 1 1 calc R . .
C7 C 0.56691(17) 0.82794(7) 0.40915(11) 0.0269(2) Uani 1 1 d . . .
C4 C 0.35429(19) 0.73235(7) 0.18424(11) 0.0296(3) Uani 1 1 d . . .
H4 H 0.3405 0.7323 0.1112 0.036 Uiso 1 1 calc R . .
C11 C 0.48516(19) 0.70947(9) 0.91474(11) 0.0353(3) Uani 1 1 d . . .
H11 H 0.5004 0.7044 0.9872 0.042 Uiso 1 1 calc R . .
C12 C 0.55921(18) 0.66641(8) 0.84784(11) 0.0312(3) Uani 1 1 d . . .
H12 H 0.6234 0.6321 0.8745 0.037 Uiso 1 1 calc R . .
C8 C 0.27279(17) 0.81864(7) 0.70493(12) 0.0290(3) Uani 1 1 d . . .
Cu2 Cu 0.0000 0.5000 0.5000 0.03467(7) Uani 1 2 d S . .
O8 O 0.70149(17) 0.59043(6) 0.68212(10) 0.0447(3) Uani 1 1 d . . .
C14 C 0.61377(19) 0.63770(7) 0.65613(12) 0.0297(3) Uani 1 1 d . . .
N4 N 0.06892(19) 0.55367(6) 0.62685(10) 0.0333(3) Uani 1 1 d . . .
N3 N 0.2066(2) 0.45052(7) 0.53830(13) 0.0394(3) Uani 1 1 d . . .
O10 O 0.2610(2) 0.52256(7) 0.21358(10) 0.0516(3) Uani 1 1 d D . .
C15 C 0.3169(2) 0.49316(9) 0.60259(14) 0.0394(3) Uani 1 1 d . . .
H15A H 0.3641 0.5262 0.5591 0.047 Uiso 1 1 calc R . .
H15B H 0.4054 0.4681 0.6370 0.047 Uiso 1 1 calc R . .
C16 C 0.2137(3) 0.52425(9) 0.68297(13) 0.0442(4) Uani 1 1 d . . .
H16A H 0.1795 0.4917 0.7324 0.053 Uiso 1 1 calc R . .
H16B H 0.2767 0.5574 0.7218 0.053 Uiso 1 1 calc R . .
N5 N 0.28169(16) 1.02440(7) 0.51530(11) 0.0352(3) Uani 1 1 d . . .
H5A H 0.1986 1.0039 0.5433 0.053 Uiso 1 1 calc R . .
H5B H 0.2551 1.0331 0.4479 0.053 Uiso 1 1 calc R . .
H5C H 0.3024 1.0615 0.5498 0.053 Uiso 1 1 calc R . .
O9 O 0.0509(2) 0.94330(9) 0.60524(16) 0.0669(5) Uani 1 1 d D . .
C17 C 0.4283(2) 0.98283(8) 0.52329(15) 0.0388(3) Uani 1 1 d . . .
H17A H 0.4057 0.9423 0.4860 0.047 Uiso 1 1 calc R . .
H17B H 0.4562 0.9726 0.5966 0.047 Uiso 1 1 calc R . .
H4A H -0.003(2) 0.5641(9) 0.6683(15) 0.033(5) Uiso 1 1 d . . .
H3A H 0.181(3) 0.4176(11) 0.5774(18) 0.049(6) Uiso 1 1 d . . .
H4B H 0.098(3) 0.5904(10) 0.6056(18) 0.050(6) Uiso 1 1 d . . .
H3B H 0.249(3) 0.4324(11) 0.491(2) 0.054(6) Uiso 1 1 d . . .
H10A H 0.273(3) 0.4821(7) 0.2364(17) 0.055(6) Uiso 1 1 d D . .
H10B H 0.228(3) 0.5469(10) 0.2693(18) 0.079(8) Uiso 1 1 d D . .
H9A H -0.027(3) 0.9446(15) 0.645(2) 0.082(10) Uiso 1 1 d D . .
H9B H 0.095(4) 0.9106(12) 0.640(2) 0.099(11) Uiso 1 1 d D . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 N2 1.9228(11) . ?
Cu1 N1 1.9549(11) . ?
Cu1 O7 2.1030(11) . ?
Cu1 O5 2.1328(11) . ?
Cu1 O1 2.2808(11) . ?
Cu1 O3 2.3041(11) . ?
N1 C6 1.3375(16) . ?
N1 C2 1.3390(17) . ?
O5 C8 1.2626(18) . ?
O3 C7 1.2461(18) . ?
N2 C9 1.3271(16) . ?
N2 C13 1.3303(16) . ?
C2 C3 1.3837(18) . ?
C2 C1 1.5188(18) . ?
C6 C5 1.3834(18) . ?
C6 C7 1.5146(19) . ?
C9 C10 1.3826(19) . ?
C9 C8 1.5162(19) . ?
O1 C1 1.2553(17) . ?
O2 C1 1.2439(17) . ?
C13 C12 1.3772(19) . ?
C13 C14 1.5109(18) . ?
C10 C11 1.384(2) . ?
O7 C14 1.2567(18) . ?
O6 C8 1.2350(18) . ?
C3 C4 1.381(2) . ?
O4 C7 1.2520(17) . ?
C5 C4 1.380(2) . ?
C11 C12 1.391(2) . ?
Cu2 N3 2.0019(16) 3_566 ?
Cu2 N3 2.0019(16) . ?
Cu2 N4 2.0080(13) 3_566 ?
Cu2 N4 2.0080(13) . ?
O8 C14 1.2389(17) . ?
N4 C16 1.473(2) . ?
N3 C15 1.469(2) . ?
C15 C16 1.505(2) . ?
N5 C17 1.467(2) . ?
C17 C17 1.516(3) 3_676 ?

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
N2 Cu1 N1 173.52(4) . . ?
N2 Cu1 O7 79.31(4) . . ?
N1 Cu1 O7 95.33(4) . . ?
N2 Cu1 O5 78.49(4) . . ?
N1 Cu1 O5 107.04(4) . . ?
O7 Cu1 O5 157.55(4) . . ?
N2 Cu1 O1 99.47(4) . . ?
N1 Cu1 O1 76.64(4) . . ?
O7 Cu1 O1 88.96(5) . . ?
O5 Cu1 O1 97.89(5) . . ?
N2 Cu1 O3 107.65(4) . . ?
N1 Cu1 O3 76.64(4) . . ?
O7 Cu1 O3 99.06(5) . . ?
O5 Cu1 O3 84.60(5) . . ?
O1 Cu1 O3 152.68(4) . . ?
C6 N1 C2 120.58(11) . . ?
C6 N1 Cu1 120.18(9) . . ?
C2 N1 Cu1 119.20(8) . . ?
C8 O5 Cu1 113.42(9) . . ?
C7 O3 Cu1 110.25(9) . . ?
C9 N2 C13 122.16(11) . . ?
C9 N2 Cu1 119.64(9) . . ?
C13 N2 Cu1 118.20(8) . . ?
N1 C2 C3 121.04(12) . . ?
N1 C2 C1 115.09(11) . . ?
C3 C2 C1 123.82(12) . . ?
N1 C6 C5 121.00(12) . . ?
N1 C6 C7 114.86(11) . . ?
C5 C6 C7 124.12(12) . . ?
N2 C9 C10 120.42(12) . . ?
N2 C9 C8 112.77(11) . . ?
C10 C9 C8 126.78(12) . . ?
C1 O1 Cu1 110.04(9) . . ?
N2 C13 C12 120.68(12) . . ?
N2 C13 C14 113.03(11) . . ?
C12 C13 C14 126.20(12) . . ?
C9 C10 C11 118.42(12) . . ?
C14 O7 Cu1 113.50(9) . . ?
C4 C3 C2 118.76(13) . . ?
O2 C1 O1 126.87(13) . . ?
O2 C1 C2 117.84(12) . . ?
O1 C1 C2 115.30(11) . . ?
C4 C5 C6 118.86(12) . . ?
O3 C7 O4 126.50(14) . . ?
O3 C7 C6 117.18(12) . . ?
O4 C7 C6 116.32(13) . . ?
C5 C4 C3 119.72(12) . . ?
C10 C11 C12 120.11(13) . . ?
C13 C12 C11 118.20(13) . . ?
O6 C8 O5 126.80(14) . . ?
O6 C8 C9 118.08(13) . . ?
O5 C8 C9 115.12(12) . . ?
N3 Cu2 N3 180.0 3_566 . ?
N3 Cu2 N4 83.80(6) 3_566 3_566 ?
N3 Cu2 N4 96.20(6) . 3_566 ?
N3 Cu2 N4 96.20(6) 3_566 . ?
N3 Cu2 N4 83.80(6) . . ?
N4 Cu2 N4 180.00(6) 3_566 . ?
O8 C14 O7 125.87(13) . . ?
O8 C14 C13 118.69(13) . . ?
O7 C14 C13 115.42(12) . . ?
C16 N4 Cu2 110.04(10) . . ?
C15 N3 Cu2 108.13(10) . . ?
N3 C15 C16 106.47(15) . . ?
N4 C16 C15 107.96(13) . . ?
N5 C17 C17 110.25(17) . 3_676 ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        35.17
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.071
_database_code_depnum_ccdc_archive 'CCDC 974946'
#######################################################################
#
#                 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_JTM390_0m
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H12 Cu N4 O6, H2 O'
_chemical_formula_sum            'C12 H14 Cu N4 O7'
_chemical_formula_iupac          ?
_chemical_formula_weight         389.81

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.986(2)
_cell_length_b                   7.6602(14)
_cell_length_c                   15.750(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.123(3)
_cell_angle_gamma                90
_cell_volume                     1442.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9847
_cell_measurement_theta_min      2.9585
_cell_measurement_theta_max      29.1152
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       Slab
_exptl_crystal_colour            blue-green
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             796

_exptl_absorpt_coefficient_mu    1.562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012b)'
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;
The diffraction data were obtained from 3 sets of 400 frames,
each of width 0.5 deg. in omega, colllected at phi = 0.00,
90.00 and 180.00 deg. and 2 sets of 800 frames, each of
width 0.45 deg in phi, collected at omega = -30.00 and 210.00
deg. The scan time was 20 sec/frame.
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker Smart APEX'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3660

_diffrn_reflns_number            25054
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_full        29.12
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_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. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 Å) while those 
attached to nitrogen and oxygen were placed in locations derived from a 
difference map and their coordinates adjusted to give N---H = 0.91 Å and 
O---H = 0.84 Å. All were included as riding contributions with isotropic 
displacement parameters 1.2 times those of the attached atoms.
;

_reflns_number_total             3804
_reflns_number_gt                3430
_reflns_threshold_expression     >2σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0847
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_number_reflns         3804
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0414P)²+1.1686P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.400
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker AXS, 2012)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2012a)'
_computing_data_reduction        'SAINT (Bruker AXS, 2012a)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker AXS, 2008)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.199257(16) 0.63369(3) 0.050645(12) 0.01203(8) Uani d . 1 . .
O O1 0.28710(10) 0.57170(17) 0.16027(8) 0.0150(2) Uani d . 1 . .
O O2 0.26778(10) 0.55265(17) 0.30058(8) 0.0167(3) Uani d . 1 . .
O O3 0.06282(10) 0.68972(18) -0.03311(8) 0.0164(2) Uani d . 1 . .
O O4 -0.11310(10) 0.79006(19) -0.03661(8) 0.0191(3) Uani d . 1 . .
O O5 -0.15541(10) 0.73563(18) 0.29419(8) 0.0166(3) Uani d . 1 . .
H H5O -0.1334 0.7189 0.3454 0.02 Uiso d R 1 . .
O O6 0.26634(12) 0.90419(18) 0.04234(10) 0.0247(3) Uani d . 1 . .
H H6A 0.2211 0.9879 0.0366 0.03 Uiso d R 1 . .
H H6B 0.3181 0.9181 0.0098 0.03 Uiso d R 1 . .
N N1 0.08579(11) 0.67153(19) 0.12745(9) 0.0115(3) Uani d . 1 . .
N N2 0.29499(11) 0.53038(19) -0.03303(9) 0.0125(3) Uani d . 1 . .
N N3 0.41804(12) 0.31658(19) -0.08545(9) 0.0147(3) Uani d . 1 . .
N N4 0.39393(14) 0.3347(2) 0.05692(10) 0.0194(3) Uani d . 1 . .
H H4A 0.4428 0.2437 0.0621 0.023 Uiso d R 1 . .
H H4B 0.3631 0.3899 0.1007 0.023 Uiso d R 1 . .
C C1 0.23202(13) 0.5832(2) 0.22699(11) 0.0127(3) Uani d . 1 . .
C C2 0.11161(14) 0.6420(2) 0.20994(11) 0.0120(3) Uani d . 1 . .
C C3 0.03400(14) 0.6616(2) 0.26983(10) 0.0130(3) Uani d . 1 . .
H H3 0.0534 0.6407 0.3285 0.016 Uiso calc R 1 . .
C C4 -0.07454(13) 0.7135(2) 0.24116(10) 0.0126(3) Uani d . 1 . .
C C5 -0.10048(13) 0.7439(2) 0.15361(10) 0.0130(3) Uani d . 1 . .
H H5 -0.1733 0.7799 0.1331 0.016 Uiso calc R 1 . .
C C6 -0.01717(13) 0.7199(2) 0.09843(10) 0.0120(3) Uani d . 1 . .
C C7 -0.02487(14) 0.7359(2) 0.00190(11) 0.0136(3) Uani d . 1 . .
C C8 0.27744(14) 0.5920(2) -0.11296(11) 0.0150(3) Uani d . 1 . .
H H8 0.2275 0.6873 -0.123 0.018 Uiso calc R 1 . .
C C9 0.32849(15) 0.5232(2) -0.18045(11) 0.0167(3) Uani d . 1 . .
H H9 0.317 0.5712 -0.236 0.02 Uiso calc R 1 . .
C C10 0.39818(14) 0.3792(2) -0.16383(11) 0.0141(3) Uani d . 1 . .
C C11 0.45285(16) 0.2871(3) -0.23370(12) 0.0211(4) Uani d . 1 . .
H H11A 0.5323 0.2691 -0.2167 0.032 Uiso calc R 1 . .
H H11B 0.4455 0.3581 -0.2856 0.032 Uiso calc R 1 . .
H H11C 0.4165 0.1739 -0.2446 0.032 Uiso calc R 1 . .
C C12 0.36849(14) 0.3959(2) -0.02121(11) 0.0131(3) Uani d . 1 . .
O O7 0.43462(10) 0.94204(17) 0.92642(8) 0.0174(3) Uani d . 1 . .
H H7A 0.4455 1.0503 0.9281 0.021 Uiso d R 1 . .
H H7B 0.3914 0.9332 0.8823 0.021 Uiso d R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 N1 . 1.9062(14) ?
Cu1 N2 . 1.9740(14) ?
Cu1 O1 . 2.0134(12) ?
Cu1 O3 . 2.0708(12) ?
Cu1 O6 . 2.2298(15) ?
O1 C1 . 1.284(2) ?
O2 C1 . 1.229(2) ?
O3 C7 . 1.272(2) ?
O4 C7 . 1.252(2) ?
O5 C4 . 1.3351(19) ?
O5 H5O . 0.8399 ?
O6 H6A . 0.84 ?
O6 H6B . 0.8401 ?
N1 C2 . 1.333(2) ?
N1 C6 . 1.337(2) ?
N2 C8 . 1.347(2) ?
N2 C12 . 1.360(2) ?
N3 C10 . 1.330(2) ?
N3 C12 . 1.354(2) ?
N4 C12 . 1.332(2) ?
N4 H4A . 0.91 ?
N4 H4B . 0.9101 ?
C1 C2 . 1.517(2) ?
C2 C3 . 1.380(2) ?
C3 C4 . 1.403(2) ?
C3 H3 . 0.95 ?
C4 C5 . 1.411(2) ?
C5 C6 . 1.382(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.521(2) ?
C8 C9 . 1.370(2) ?
C8 H8 . 0.95 ?
C9 C10 . 1.397(2) ?
C9 H9 . 0.95 ?
C10 C11 . 1.497(2) ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
O7 H7A . 0.84 ?
O7 H7B . 0.84 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 Cu1 N2 . . 163.75(6) ?
N1 Cu1 O1 . . 81.06(5) ?
N2 Cu1 O1 . . 100.64(6) ?
N1 Cu1 O3 . . 78.81(5) ?
N2 Cu1 O3 . . 97.36(5) ?
O1 Cu1 O3 . . 159.31(5) ?
N1 Cu1 O6 . . 99.94(6) ?
N2 Cu1 O6 . . 95.97(6) ?
O1 Cu1 O6 . . 95.79(6) ?
O3 Cu1 O6 . . 92.38(6) ?
C1 O1 Cu1 . . 114.70(10) ?
C7 O3 Cu1 . . 114.89(11) ?
C4 O5 H5O . . 112.9 ?
Cu1 O6 H6A . . 118.9 ?
Cu1 O6 H6B . . 116.0 ?
H6A O6 H6B . . 109.7 ?
C2 N1 C6 . . 121.60(14) ?
C2 N1 Cu1 . . 117.80(11) ?
C6 N1 Cu1 . . 120.55(11) ?
C8 N2 C12 . . 116.71(14) ?
C8 N2 Cu1 . . 115.11(11) ?
C12 N2 Cu1 . . 127.91(12) ?
C10 N3 C12 . . 118.24(15) ?
C12 N4 H4A . . 117.1 ?
C12 N4 H4B . . 117.3 ?
H4A N4 H4B . . 125.5 ?
O2 C1 O1 . . 126.45(15) ?
O2 C1 C2 . . 119.09(15) ?
O1 C1 C2 . . 114.46(14) ?
N1 C2 C3 . . 121.81(15) ?
N1 C2 C1 . . 111.97(14) ?
C3 C2 C1 . . 126.22(15) ?
C2 C3 C4 . . 117.76(15) ?
C2 C3 H3 . . 121.1 ?
C4 C3 H3 . . 121.1 ?
O5 C4 C3 . . 122.18(15) ?
O5 C4 C5 . . 118.13(14) ?
C3 C4 C5 . . 119.69(15) ?
C6 C5 C4 . . 118.31(15) ?
C6 C5 H5 . . 120.8 ?
C4 C5 H5 . . 120.8 ?
N1 C6 C5 . . 120.83(15) ?
N1 C6 C7 . . 110.61(14) ?
C5 C6 C7 . . 128.53(14) ?
O4 C7 O3 . . 125.31(16) ?
O4 C7 C6 . . 119.96(14) ?
O3 C7 C6 . . 114.73(14) ?
N2 C8 C9 . . 122.84(16) ?
N2 C8 H8 . . 118.6 ?
C9 C8 H8 . . 118.6 ?
C8 C9 C10 . . 116.93(16) ?
C8 C9 H9 . . 121.5 ?
C10 C9 H9 . . 121.5 ?
N3 C10 C9 . . 121.57(15) ?
N3 C10 C11 . . 116.99(16) ?
C9 C10 C11 . . 121.44(16) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N4 C12 N3 . . 116.69(15) ?
N4 C12 N2 . . 119.75(15) ?
N3 C12 N2 . . 123.55(16) ?
H7A O7 H7B . . 101.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 Cu1 O1 C1 . . . . 0.44(12) ?
N2 Cu1 O1 C1 . . . . -163.17(12) ?
O3 Cu1 O1 C1 . . . . -13.1(2) ?
O6 Cu1 O1 C1 . . . . 99.63(12) ?
N1 Cu1 O3 C7 . . . . 5.73(13) ?
N2 Cu1 O3 C7 . . . . 169.72(13) ?
O1 Cu1 O3 C7 . . . . 19.4(2) ?
O6 Cu1 O3 C7 . . . . -93.94(13) ?
N2 Cu1 N1 C2 . . . . 96.8(2) ?
O1 Cu1 N1 C2 . . . . -0.57(12) ?
O3 Cu1 N1 C2 . . . . 174.59(13) ?
O6 Cu1 N1 C2 . . . . -94.93(13) ?
N2 Cu1 N1 C6 . . . . -80.8(3) ?
O1 Cu1 N1 C6 . . . . -178.17(14) ?
O3 Cu1 N1 C6 . . . . -3.01(13) ?
O6 Cu1 N1 C6 . . . . 87.47(13) ?
N1 Cu1 N2 C8 . . . . 104.1(2) ?
O1 Cu1 N2 C8 . . . . -161.27(12) ?
O3 Cu1 N2 C8 . . . . 28.98(13) ?
O6 Cu1 N2 C8 . . . . -64.21(13) ?
N1 Cu1 N2 C12 . . . . -69.7(3) ?
O1 Cu1 N2 C12 . . . . 24.90(15) ?
O3 Cu1 N2 C12 . . . . -144.85(14) ?
O6 Cu1 N2 C12 . . . . 121.96(14) ?
Cu1 O1 C1 O2 . . . . -179.75(14) ?
Cu1 O1 C1 C2 . . . . -0.25(18) ?
C6 N1 C2 C3 . . . . -0.7(3) ?
Cu1 N1 C2 C3 . . . . -178.32(13) ?
C6 N1 C2 C1 . . . . 178.15(14) ?
Cu1 N1 C2 C1 . . . . 0.58(18) ?
O2 C1 C2 N1 . . . . 179.35(15) ?
O1 C1 C2 N1 . . . . -0.2(2) ?
O2 C1 C2 C3 . . . . -1.8(3) ?
O1 C1 C2 C3 . . . . 178.65(16) ?
N1 C2 C3 C4 . . . . 0.3(3) ?
C1 C2 C3 C4 . . . . -178.45(15) ?
C2 C3 C4 O5 . . . . 179.88(15) ?
C2 C3 C4 C5 . . . . -0.2(2) ?
O5 C4 C5 C6 . . . . -179.57(15) ?
C3 C4 C5 C6 . . . . 0.5(2) ?
C2 N1 C6 C5 . . . . 1.1(3) ?
Cu1 N1 C6 C5 . . . . 178.58(12) ?
C2 N1 C6 C7 . . . . -177.19(15) ?
Cu1 N1 C6 C7 . . . . 0.31(19) ?
C4 C5 C6 N1 . . . . -0.9(3) ?
C4 C5 C6 C7 . . . . 177.00(16) ?
Cu1 O3 C7 O4 . . . . 173.35(14) ?
Cu1 O3 C7 C6 . . . . -7.09(19) ?
N1 C6 C7 O4 . . . . -175.74(16) ?
C5 C6 C7 O4 . . . . 6.2(3) ?
N1 C6 C7 O3 . . . . 4.7(2) ?
C5 C6 C7 O3 . . . . -173.42(17) ?
C12 N2 C8 C9 . . . . 1.1(3) ?
Cu1 N2 C8 C9 . . . . -173.47(14) ?
N2 C8 C9 C10 . . . . 2.3(3) ?
C12 N3 C10 C9 . . . . 0.2(2) ?
C12 N3 C10 C11 . . . . -179.14(15) ?
C8 C9 C10 N3 . . . . -2.9(3) ?
C8 C9 C10 C11 . . . . 176.36(16) ?
C10 N3 C12 N4 . . . . -177.19(16) ?
C10 N3 C12 N2 . . . . 3.5(2) ?
C8 N2 C12 N4 . . . . 176.61(16) ?
Cu1 N2 C12 N4 . . . . -9.6(2) ?
C8 N2 C12 N3 . . . . -4.1(2) ?
Cu1 N2 C12 N3 . . . . 169.61(12) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O7 H7B O2 4_576 0.84 1.89 2.7128(17) 165 ?
O7 H7A N3 1_566 0.84 2.07 2.881(2) 161 ?
N4 H4B O1 . 0.91 1.94 2.808(2) 158 ?
N4 H4A O7 3_666 0.91 2.04 2.951(2) 174 ?
O6 H6B O7 1_554 0.84 1.99 2.8312(19) 176 ?
O6 H6A O4 3_575 0.84 2.14 2.974(2) 173 ?
O5 H5O O4 4_576 0.84 1.86 2.6840(18) 167 ?


_database_code_depnum_ccdc_archive 'CCDC 974947'
#######################################################################
#
#                 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_jtm389_1m
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C6 H6 Co N2, 2(H2 O)'
_chemical_formula_sum            'C6 H10 Co N2 O8'
_chemical_formula_iupac          ?
_chemical_formula_weight         297.09

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_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                   12.5445(4)
_cell_length_b                   7.3874(3)
_cell_length_c                   11.8763(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.118(1)
_cell_angle_gamma                90
_cell_volume                     1026.68(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7909
_cell_measurement_theta_min      3.9902
_cell_measurement_theta_max      69.6724
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604

_exptl_absorpt_coefficient_mu    13.529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012b)'
_exptl_absorpt_correction_T_min  0.28
_exptl_absorpt_correction_T_max  0.41

_exptl_special_details           
;
The diffraction data were obtained from 8 sets of 340 frames,
each of width 0.5 deg. in omega, collected at phi = 0.00,
90.00, 180.00 and 270.00 deg. and at 2 theta = -50.00 and -90.00
deg. and 4 sets of 340 frames, each of width 0.5 deg. in omega
collected at 2 theta = -90.00 deg. and phi = 45.00, 135.00,
225.00 and 315.00 deg. The scan time was 15 sec/frame.
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'INCOATEC I\mS micro-focus source'
_diffrn_source_type              ?

_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  mirror

_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            8419
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_theta_min         7.09
_diffrn_reflns_theta_max         69.67
_diffrn_reflns_theta_full        69.67
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_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.
;

_reflns_number_total             951
_reflns_number_gt                937
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0198
_refine_ls_wR_factor_gt          0.0548
_refine_ls_wR_factor_ref         0.0551
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_number_reflns         951
_refine_ls_number_parameters     80
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0291P)²+1.4473P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.283
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00235(19)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker AXS, 2012)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2012a)'
_computing_data_reduction        'SAINT  (Bruker AXS, 2012a)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker AXS, 2008)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co Co1 0.25 0.25 1.0 0.00589(15) Uani d S 1 . .
O O1 0.01710(9) -0.15324(14) 0.87713(9) 0.0122(3) Uani d . 1 . .
O O2 0.17886(8) -0.00512(13) 0.97568(9) 0.0093(2) Uani d . 1 . .
O O3 0.31942(9) 0.18767(16) 0.86819(9) 0.0119(3) Uani d . 1 . .
H H3A 0.3828 0.2381 0.877 0.014 Uiso d R 1 . .
H H3B 0.2755 0.2174 0.7975 0.014 Uiso d R 1 . .
N N1 0.09054(11) 0.29684(18) 0.85822(11) 0.0077(3) Uani d . 1 . .
C C1 0.08141(12) -0.0226(2) 0.89094(12) 0.0080(3) Uani d . 1 . .
C C2 0.04226(12) 0.1401(2) 0.80738(13) 0.0076(3) Uani d . 1 . .
C C3 0.04797(13) 0.4521(2) 0.80244(13) 0.0097(3) Uani d . 1 . .
H H3 0.0838 0.5634 0.8349 0.012 Uiso calc R 1 . .
O O4 0.31784(11) 0.22553(16) 0.35309(11) 0.0150(3) Uani d . 1 . .
H H4A 0.3208 0.2954 0.411 0.018 Uiso d R 1 . .
H H4B 0.3124 0.1177 0.3754 0.018 Uiso d R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Co1 O2 7_557 2.0606(10) ?
Co1 O2 . 2.0606(10) ?
Co1 O3 . 2.0984(10) ?
Co1 O3 7_557 2.0984(10) ?
Co1 N1 . 2.1282(13) ?
Co1 N1 7_557 2.1283(13) ?
O1 C1 . 1.2301(18) ?
O2 C1 . 1.2797(18) ?
O3 H3A . 0.8501 ?
O3 H3B . 0.85 ?
N1 C3 . 1.336(2) ?
N1 C2 . 1.345(2) ?
C1 C2 . 1.523(2) ?
C2 C2 2_556 1.393(3) ?
C3 C3 2_556 1.386(3) ?
C3 H3 . 0.95 ?
O4 H4A . 0.8501 ?
O4 H4B . 0.85 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 Co1 O2 7_557 . 180.0 ?
O2 Co1 O3 7_557 . 91.72(4) ?
O2 Co1 O3 . . 88.28(4) ?
O2 Co1 O3 7_557 7_557 88.28(4) ?
O2 Co1 O3 . 7_557 91.72(4) ?
O3 Co1 O3 . 7_557 180.00(7) ?
O2 Co1 N1 7_557 . 101.44(5) ?
O2 Co1 N1 . . 78.56(5) ?
O3 Co1 N1 . . 88.27(4) ?
O3 Co1 N1 7_557 . 91.73(4) ?
O2 Co1 N1 7_557 7_557 78.56(5) ?
O2 Co1 N1 . 7_557 101.44(5) ?
O3 Co1 N1 . 7_557 91.73(4) ?
O3 Co1 N1 7_557 7_557 88.27(4) ?
N1 Co1 N1 . 7_557 180.0 ?
C1 O2 Co1 . . 116.46(9) ?
Co1 O3 H3A . . 115.7 ?
Co1 O3 H3B . . 112.6 ?
H3A O3 H3B . . 104.6 ?
C3 N1 C2 . . 118.80(13) ?
C3 N1 Co1 . . 128.74(11) ?
C2 N1 Co1 . . 110.98(10) ?
O1 C1 O2 . . 125.38(13) ?
O1 C1 C2 . . 119.35(13) ?
O2 C1 C2 . . 115.15(12) ?
N1 C2 C2 . 2_556 120.01(8) ?
N1 C2 C1 . . 113.56(13) ?
C2 C2 C1 2_556 . 126.20(8) ?
N1 C3 C3 . 2_556 120.56(9) ?
N1 C3 H3 . . 119.7 ?
C3 C3 H3 2_556 . 119.7 ?
H4A O4 H4B . . 107.6 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 Co1 O2 C1 . . . . -86.16(10) ?
O3 Co1 O2 C1 7_557 . . . 93.84(10) ?
N1 Co1 O2 C1 . . . . 2.42(10) ?
N1 Co1 O2 C1 7_557 . . . -177.58(10) ?
O2 Co1 N1 C3 7_557 . . . -1.27(13) ?
O2 Co1 N1 C3 . . . . 178.73(13) ?
O3 Co1 N1 C3 . . . . -92.68(13) ?
O3 Co1 N1 C3 7_557 . . . 87.32(13) ?
O2 Co1 N1 C2 7_557 . . . 164.45(9) ?
O2 Co1 N1 C2 . . . . -15.55(9) ?
O3 Co1 N1 C2 . . . . 73.04(10) ?
O3 Co1 N1 C2 7_557 . . . -106.96(10) ?
Co1 O2 C1 O1 . . . . -165.97(12) ?
Co1 O2 C1 C2 . . . . 9.96(15) ?
C3 N1 C2 C2 . . . 2_556 6.8(2) ?
Co1 N1 C2 C2 . . . 2_556 -160.49(14) ?
C3 N1 C2 C1 . . . . -167.97(12) ?
Co1 N1 C2 C1 . . . . 24.72(14) ?
O1 C1 C2 N1 . . . . 152.21(13) ?
O2 C1 C2 N1 . . . . -23.98(17) ?
O1 C1 C2 C2 . . . 2_556 -22.2(3) ?
O2 C1 C2 C2 . . . 2_556 161.61(17) ?
C2 N1 C3 C3 . . . 2_556 3.5(2) ?
Co1 N1 C3 C3 . . . 2_556 168.22(14) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3A O1 3 0.85 1.87 2.7114(15) 173 ?
O3 H3B O4 7_556 0.85 1.80 2.6498(16) 179 ?
O4 H4A O2 4_556 0.85 1.99 2.8347(16) 170 ?
O4 H4B O3 6 0.85 2.26 3.0574(17) 156 ?

_database_code_depnum_ccdc_archive 'CCDC 974948'
#######################################################################
#
#                 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_mm2_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 Cu2 N2 O15'
_chemical_formula_weight         583.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.3425(5)
_cell_length_b                   27.1640(17)
_cell_length_c                   9.5946(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.111(2)
_cell_angle_gamma                90.00
_cell_volume                     2152.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      39.26

_exptl_crystal_description       Block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    2.055
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5776
_exptl_absorpt_correction_T_max  0.5776
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating anode X-ray tube'
_diffrn_source_type              'Bruker-Nonius FR 591'
_diffrn_source_power             50
_diffrn_source_current           70
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            55047
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         39.61
_reflns_number_total             12365
_reflns_number_gt                11576
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.0580P)²+3.3794P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         12365
_refine_ls_number_parameters     341
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_restrained_S_all      1.171
_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
C1 C 0.04305(16) 0.18274(5) 0.61970(14) 0.00863(18) Uani 1 1 d . . .
C2 C 0.14517(16) 0.21446(5) 0.53715(13) 0.00792(17) Uani 1 1 d . . .
C3 C 0.14553(18) 0.26565(5) 0.53184(16) 0.0113(2) Uani 1 1 d . . .
H3 H 0.0757 0.2845 0.5812 0.014 Uiso 1 1 calc R . .
C4 C 0.2514(2) 0.28852(5) 0.45196(17) 0.0132(2) Uani 1 1 d . . .
H4 H 0.2561 0.3234 0.4482 0.016 Uiso 1 1 calc R . .
C5 C 0.35040(19) 0.26041(5) 0.37757(16) 0.0122(2) Uani 1 1 d . . .
H5 H 0.4234 0.2756 0.3231 0.015 Uiso 1 1 calc R . .
C6 C 0.33884(16) 0.20946(5) 0.38571(14) 0.00840(18) Uani 1 1 d . . .
C7 C 0.42443(16) 0.17235(5) 0.30454(14) 0.00936(18) Uani 1 1 d . . .
C8 C 0.07968(15) 0.02993(5) 0.33602(13) 0.00729(17) Uani 1 1 d . . .
C9 C 0.19277(15) 0.00777(4) 0.45586(13) 0.00657(16) Uani 1 1 d . . .
C10 C 0.20587(16) -0.04202(5) 0.48902(14) 0.00827(18) Uani 1 1 d . . .
H10 H 0.1403 -0.0657 0.4349 0.010 Uiso 1 1 calc R . .
C11 C 0.31765(17) -0.05627(5) 0.60375(14) 0.00921(18) Uani 1 1 d . . .
H11 H 0.3269 -0.0899 0.6306 0.011 Uiso 1 1 calc R . .
C12 C 0.41582(16) -0.02099(5) 0.67900(14) 0.00894(18) Uani 1 1 d . . .
H12 H 0.4946 -0.0301 0.7560 0.011 Uiso 1 1 calc R . .
C13 C 0.39517(15) 0.02798(5) 0.63813(13) 0.00699(17) Uani 1 1 d . . .
C14 C 0.49544(15) 0.07036(5) 0.70465(13) 0.00741(17) Uani 1 1 d . . .
Cu1 Cu 0.76190(2) 0.100754(7) 0.944097(18) 0.00869(4) Uani 1 1 d . . .
Cu2 Cu 0.25007(2) 0.113957(6) 0.486452(19) 0.00883(4) Uani 1 1 d . . .
N1 N 0.24055(13) 0.18799(4) 0.46587(12) 0.00692(15) Uani 1 1 d . . .
N2 N 0.28419(13) 0.04148(4) 0.53113(11) 0.00639(15) Uani 1 1 d . . .
O1 O 0.06679(14) 0.13644(4) 0.61296(12) 0.01003(15) Uani 1 1 d . . .
O2 O -0.05329(15) 0.20294(4) 0.68958(14) 0.01398(19) Uani 1 1 d . . .
O3 O 0.38430(14) 0.12766(4) 0.31947(12) 0.01061(16) Uani 1 1 d . . .
O4 O 0.52122(15) 0.18763(5) 0.22667(13) 0.01511(19) Uani 1 1 d . . .
O5 O 0.08014(13) 0.07656(4) 0.32807(11) 0.00970(16) Uani 1 1 d . . .
O6 O -0.00520(14) 0.00156(4) 0.25367(12) 0.01065(16) Uani 1 1 d . . .
O7 O 0.45590(14) 0.11325(4) 0.65942(12) 0.01036(16) Uani 1 1 d . . .
O8 O 0.61096(13) 0.05921(4) 0.79657(11) 0.00982(16) Uani 1 1 d . . .
O9 O 0.80284(17) 0.03146(4) 1.02794(13) 0.0154(2) Uani 1 1 d D . .
H19 H 0.864(4) 0.0205(12) 1.103(2) 0.023 Uiso 1 1 d D . .
H29 H 0.776(4) 0.0021(6) 0.993(3) 0.023 Uiso 1 1 d D . .
O10 O 0.91594(14) 0.13159(4) 1.11214(11) 0.01009(16) Uani 1 1 d D . .
H110 H 0.955(4) 0.1109(9) 1.179(2) 0.015 Uiso 1 1 d D . .
H210 H 0.882(4) 0.1579(7) 1.154(3) 0.015 Uiso 1 1 d D . .
O11 O 0.71212(13) 0.16359(4) 0.82074(12) 0.01039(16) Uani 1 1 d D . .
H111 H 0.786(3) 0.1722(11) 0.770(3) 0.016 Uiso 1 1 d D . .
H211 H 0.636(3) 0.1579(11) 0.749(2) 0.016 Uiso 1 1 d D . .
O12 O 0.56071(16) 0.11607(5) 1.03728(15) 0.0162(2) Uani 1 1 d D . .
H112 H 0.474(3) 0.0974(11) 1.028(4) 0.024 Uiso 1 1 d D . .
H212 H 0.554(6) 0.1393(12) 1.100(4) 0.052(13) Uiso 1 1 d D . .
O13 O 0.97874(13) 0.08917(4) 0.84815(11) 0.00897(15) Uani 1 1 d D . .
H113 H 0.999(4) 0.1054(10) 0.773(2) 0.013 Uiso 1 1 d D . .
H213 H 0.980(4) 0.0591(5) 0.816(3) 0.013 Uiso 1 1 d D . .
O1W O 0.25987(14) 0.07168(4) 0.05606(12) 0.01245(17) Uani 1 1 d D . .
H2W1 H 0.257(4) 0.0829(12) 0.1422(16) 0.019 Uiso 1 1 d D . .
H1W1 H 0.178(3) 0.0804(12) -0.008(3) 0.019 Uiso 1 1 d D . .
O2W O 0.85021(16) 0.20574(4) 0.27516(15) 0.0167(2) Uani 1 1 d D . .
H1W2 H 0.7449(12) 0.2046(13) 0.269(4) 0.025 Uiso 1 1 d D . .
H2W2 H 0.885(4) 0.2352(6) 0.257(4) 0.025 Uiso 1 1 d D . .


_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 O2 1.2444(17) . ?
C1 O1 1.2763(17) . ?
C1 C2 1.5119(18) . ?
C2 N1 1.3308(17) . ?
C2 C3 1.3917(19) . ?
C3 C4 1.395(2) . ?
C4 C5 1.393(2) . ?
C5 C6 1.3904(19) . ?
C6 N1 1.3348(17) . ?
C6 C7 1.5131(19) . ?
C7 O4 1.2461(18) . ?
C7 O3 1.2728(18) . ?
C8 O6 1.2497(16) . ?
C8 O5 1.2688(16) . ?
C8 C9 1.5061(17) . ?
C9 N2 1.3364(16) . ?
C9 C10 1.3903(18) . ?
C10 C11 1.3933(18) . ?
C11 C12 1.3940(19) . ?
C12 C13 1.3906(18) . ?
C13 N2 1.3332(16) . ?
C13 C14 1.5105(17) . ?
C14 O8 1.2484(16) . ?
C14 O7 1.2706(16) . ?
Cu1 O12 2.0525(12) . ?
Cu1 O9 2.0565(11) . ?
Cu1 O11 2.0853(11) . ?
Cu1 O8 2.0879(10) . ?
Cu1 O10 2.0899(10) . ?
Cu1 O13 2.1654(11) . ?
Cu2 N1 2.0213(11) . ?
Cu2 N2 2.0265(11) . ?
Cu2 O3 2.1131(11) . ?
Cu2 O1 2.1697(11) . ?
Cu2 O5 2.1779(10) . ?
Cu2 O7 2.2134(11) . ?

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
O2 C1 O1 125.34(13) . . ?
O2 C1 C2 119.04(12) . . ?
O1 C1 C2 115.60(11) . . ?
N1 C2 C3 121.09(12) . . ?
N1 C2 C1 112.54(11) . . ?
C3 C2 C1 126.37(12) . . ?
C2 C3 C4 118.04(13) . . ?
C5 C4 C3 120.31(13) . . ?
C6 C5 C4 117.78(13) . . ?
N1 C6 C5 121.35(12) . . ?
N1 C6 C7 112.24(11) . . ?
C5 C6 C7 126.35(12) . . ?
O4 C7 O3 126.03(13) . . ?
O4 C7 C6 118.65(13) . . ?
O3 C7 C6 115.26(12) . . ?
O6 C8 O5 125.72(12) . . ?
O6 C8 C9 118.31(11) . . ?
O5 C8 C9 115.97(11) . . ?
N2 C9 C10 121.49(11) . . ?
N2 C9 C8 112.77(10) . . ?
C10 C9 C8 125.74(11) . . ?
C9 C10 C11 118.25(11) . . ?
C10 C11 C12 119.81(12) . . ?
C13 C12 C11 118.11(11) . . ?
N2 C13 C12 121.68(11) . . ?
N2 C13 C14 113.50(11) . . ?
C12 C13 C14 124.80(11) . . ?
O8 C14 O7 126.94(12) . . ?
O8 C14 C13 116.10(11) . . ?
O7 C14 C13 116.94(11) . . ?
O12 Cu1 O9 96.67(6) . . ?
O12 Cu1 O11 88.37(5) . . ?
O9 Cu1 O11 168.54(5) . . ?
O12 Cu1 O8 87.30(5) . . ?
O9 Cu1 O8 79.72(4) . . ?
O11 Cu1 O8 90.28(4) . . ?
O12 Cu1 O10 91.97(5) . . ?
O9 Cu1 O10 90.85(4) . . ?
O11 Cu1 O10 99.29(4) . . ?
O8 Cu1 O10 170.39(4) . . ?
O12 Cu1 O13 176.53(5) . . ?
O9 Cu1 O13 86.02(5) . . ?
O11 Cu1 O13 89.38(4) . . ?
O8 Cu1 O13 95.36(4) . . ?
O10 Cu1 O13 85.79(4) . . ?
N1 Cu2 N2 171.79(4) . . ?
N1 Cu2 O3 76.61(4) . . ?
N2 Cu2 O3 104.94(4) . . ?
N1 Cu2 O1 75.73(4) . . ?
N2 Cu2 O1 104.13(4) . . ?
O3 Cu2 O1 149.91(4) . . ?
N1 Cu2 O5 112.54(4) . . ?
N2 Cu2 O5 75.67(4) . . ?
O3 Cu2 O5 85.16(4) . . ?
O1 Cu2 O5 94.64(4) . . ?
N1 Cu2 O7 95.59(4) . . ?
N2 Cu2 O7 76.24(4) . . ?
O3 Cu2 O7 97.58(5) . . ?
O1 Cu2 O7 96.68(4) . . ?
O5 Cu2 O7 151.51(4) . . ?
C2 N1 C6 121.37(11) . . ?
C2 N1 Cu2 120.35(9) . . ?
C6 N1 Cu2 118.17(9) . . ?
C13 N2 C9 120.61(11) . . ?
C13 N2 Cu2 119.45(9) . . ?
C9 N2 Cu2 119.93(8) . . ?
C1 O1 Cu2 115.62(9) . . ?
C7 O3 Cu2 115.42(9) . . ?
C8 O5 Cu2 115.52(8) . . ?
C14 O7 Cu2 113.61(8) . . ?
C14 O8 Cu1 132.81(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
O2 C1 C2 N1 -179.03(13) . . . . ?
O1 C1 C2 N1 2.27(17) . . . . ?
O2 C1 C2 C3 1.1(2) . . . . ?
O1 C1 C2 C3 -177.63(14) . . . . ?
N1 C2 C3 C4 -1.3(2) . . . . ?
C1 C2 C3 C4 178.54(14) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 N1 -2.3(2) . . . . ?
C4 C5 C6 C7 174.69(14) . . . . ?
N1 C6 C7 O4 -179.25(13) . . . . ?
C5 C6 C7 O4 3.5(2) . . . . ?
N1 C6 C7 O3 3.29(17) . . . . ?
C5 C6 C7 O3 -173.93(14) . . . . ?
O6 C8 C9 N2 176.04(12) . . . . ?
O5 C8 C9 N2 -3.78(17) . . . . ?
O6 C8 C9 C10 -3.8(2) . . . . ?
O5 C8 C9 C10 176.39(13) . . . . ?
N2 C9 C10 C11 0.0(2) . . . . ?
C8 C9 C10 C11 179.81(13) . . . . ?
C9 C10 C11 C12 -1.9(2) . . . . ?
C10 C11 C12 C13 1.6(2) . . . . ?
C11 C12 C13 N2 0.6(2) . . . . ?
C11 C12 C13 C14 -177.58(13) . . . . ?
N2 C13 C14 O8 -173.55(12) . . . . ?
C12 C13 C14 O8 4.8(2) . . . . ?
N2 C13 C14 O7 4.99(17) . . . . ?
C12 C13 C14 O7 -176.69(13) . . . . ?
C3 C2 N1 C6 -0.6(2) . . . . ?
C1 C2 N1 C6 179.45(12) . . . . ?
C3 C2 N1 Cu2 175.48(10) . . . . ?
C1 C2 N1 Cu2 -4.42(15) . . . . ?
C5 C6 N1 C2 2.5(2) . . . . ?
C7 C6 N1 C2 -174.85(12) . . . . ?
C5 C6 N1 Cu2 -173.68(11) . . . . ?
C7 C6 N1 Cu2 8.94(14) . . . . ?
N2 Cu2 N1 C2 -86.4(3) . . . . ?
O3 Cu2 N1 C2 171.71(11) . . . . ?
O1 Cu2 N1 C2 3.69(10) . . . . ?
O5 Cu2 N1 C2 92.83(10) . . . . ?
O7 Cu2 N1 C2 -91.80(10) . . . . ?
N2 Cu2 N1 C6 89.9(3) . . . . ?
O3 Cu2 N1 C6 -12.04(10) . . . . ?
O1 Cu2 N1 C6 179.94(11) . . . . ?
O5 Cu2 N1 C6 -90.92(10) . . . . ?
O7 Cu2 N1 C6 84.45(10) . . . . ?
C12 C13 N2 C9 -2.57(19) . . . . ?
C14 C13 N2 C9 175.81(11) . . . . ?
C12 C13 N2 Cu2 175.65(10) . . . . ?
C14 C13 N2 Cu2 -5.97(15) . . . . ?
C10 C9 N2 C13 2.25(19) . . . . ?
C8 C9 N2 C13 -177.58(11) . . . . ?
C10 C9 N2 Cu2 -175.96(10) . . . . ?
C8 C9 N2 Cu2 4.21(15) . . . . ?
N1 Cu2 N2 C13 -1.6(4) . . . . ?
O3 Cu2 N2 C13 98.26(10) . . . . ?
O1 Cu2 N2 C13 -89.61(10) . . . . ?
O5 Cu2 N2 C13 179.14(11) . . . . ?
O7 Cu2 N2 C13 3.94(10) . . . . ?
N1 Cu2 N2 C9 176.6(3) . . . . ?
O3 Cu2 N2 C9 -83.51(10) . . . . ?
O1 Cu2 N2 C9 88.62(10) . . . . ?
O5 Cu2 N2 C9 -2.63(10) . . . . ?
O7 Cu2 N2 C9 -177.83(11) . . . . ?
O2 C1 O1 Cu2 -177.97(12) . . . . ?
C2 C1 O1 Cu2 0.65(15) . . . . ?
N1 Cu2 O1 C1 -2.20(10) . . . . ?
N2 Cu2 O1 C1 169.34(10) . . . . ?
O3 Cu2 O1 C1 -25.95(15) . . . . ?
O5 Cu2 O1 C1 -114.29(10) . . . . ?
O7 Cu2 O1 C1 91.90(10) . . . . ?
O4 C7 O3 Cu2 169.54(12) . . . . ?
C6 C7 O3 Cu2 -13.22(15) . . . . ?
N1 Cu2 O3 C7 13.79(10) . . . . ?
N2 Cu2 O3 C7 -157.90(10) . . . . ?
O1 Cu2 O3 C7 37.44(15) . . . . ?
O5 Cu2 O3 C7 128.34(10) . . . . ?
O7 Cu2 O3 C7 -80.19(10) . . . . ?
O6 C8 O5 Cu2 -178.08(11) . . . . ?
C9 C8 O5 Cu2 1.72(15) . . . . ?
N1 Cu2 O5 C8 -179.58(10) . . . . ?
N2 Cu2 O5 C8 0.30(10) . . . . ?
O3 Cu2 O5 C8 107.09(10) . . . . ?
O1 Cu2 O5 C8 -103.11(10) . . . . ?
O7 Cu2 O5 C8 10.11(16) . . . . ?
O8 C14 O7 Cu2 176.55(12) . . . . ?
C13 C14 O7 Cu2 -1.81(15) . . . . ?
N1 Cu2 O7 C14 178.29(10) . . . . ?
N2 Cu2 O7 C14 -0.92(10) . . . . ?
O3 Cu2 O7 C14 -104.52(10) . . . . ?
O1 Cu2 O7 C14 102.04(10) . . . . ?
O5 Cu2 O7 C14 -10.70(16) . . . . ?
O7 C14 O8 Cu1 13.6(2) . . . . ?
C13 C14 O8 Cu1 -167.98(9) . . . . ?
O12 Cu1 O8 C14 65.27(14) . . . . ?
O9 Cu1 O8 C14 162.55(14) . . . . ?
O11 Cu1 O8 C14 -23.09(14) . . . . ?
O10 Cu1 O8 C14 151.1(2) . . . . ?
O13 Cu1 O8 C14 -112.49(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.948
_refine_diff_density_min         -1.582
_refine_diff_density_rms         0.152
_database_code_depnum_ccdc_archive 'CCDC 974949'
