# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_Compound1
_audit_block_doi                 10.5517/cc139xfr
_database_code_depnum_ccdc_archive 'CCDC 1022424'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C4QI00129J 2015
_audit_update_record             
;
2014-09-01 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H4 Cu N4 O10'
_chemical_formula_weight         403.71

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'
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   P21/n

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                   5.2386(10)
_cell_length_b                   11.3793(17)
_cell_length_c                   10.8544(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.222(11)
_cell_angle_gamma                90.00
_cell_volume                     646.56(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2895
_cell_measurement_theta_min      2.01
_cell_measurement_theta_max      24.51

_exptl_crystal_description       reactangular
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.074
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             402
_exptl_absorpt_coefficient_mu    1.763
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8718
_exptl_absorpt_correction_T_max  0.9328
_exptl_absorpt_process_details   SADABS

_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            4707
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         23.84
_reflns_number_total             964
_reflns_number_gt                749
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART (Bruker,2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 1.4.1'
_computing_publication_material  'PLATON (Spek, 2003)'

_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)+(0.1289P)²+0.5732P] 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         964
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1868
_refine_ls_wR_factor_gt          0.1733
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 0.0000 1.0000 0.0295(5) Uani 1 2 d S . .
C4 C 1.3071(12) 0.4345(6) 1.1009(6) 0.0289(15) Uani 1 1 d . . .
C3 C 1.5534(11) 0.2726(5) 1.1777(6) 0.0276(15) Uani 1 1 d . . .
H1 H 1.6947 0.2469 1.2247 0.033 Uiso 1 1 calc R . .
C2 C 1.4047(11) 0.1915(5) 1.1221(6) 0.0285(15) Uani 1 1 d . . .
O1 O 1.0234(7) 0.1698(4) 0.9901(4) 0.0321(12) Uani 1 1 d . . .
O2 O 1.2998(9) -0.0139(3) 1.1039(5) 0.0331(12) Uani 1 1 d . . .
N2 N 1.5116(9) 0.3890(4) 1.1701(5) 0.0287(13) Uani 1 1 d . . .
N1 N 1.1534(9) 0.3519(4) 1.0426(5) 0.0296(13) Uani 1 1 d . . .
O4 O 1.2662(9) 0.5382(4) 1.0923(4) 0.0373(12) Uani 1 1 d . . .
H2 H 1.1382 0.5491 1.0478 0.056 Uiso 1 1 calc R . .
O3 O 1.6809(9) 0.0375(4) 1.1860(5) 0.0416(13) Uani 1 1 d . . .
C1 C 1.1885(11) 0.2320(5) 1.0492(6) 0.0264(15) Uani 1 1 d . . .
C5 C 1.4665(11) 0.0638(5) 1.1389(6) 0.0272(15) Uani 1 1 d . . .
OW O 1.4717(11) -0.2404(5) 1.1661(6) 0.0663(17) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0335(8) 0.0072(8) 0.0467(9) 0.0016(4) -0.0122(5) -0.0011(4)
C4 0.032(4) 0.016(4) 0.038(4) -0.002(3) -0.003(3) 0.003(3)
C3 0.032(4) 0.014(4) 0.037(4) 0.002(3) -0.008(3) 0.004(2)
C2 0.030(3) 0.015(4) 0.039(4) 0.000(3) -0.006(3) -0.001(2)
O1 0.033(3) 0.008(3) 0.053(3) 0.0009(19) -0.017(2) -0.0019(16)
O2 0.037(3) 0.005(2) 0.056(3) 0.0014(19) -0.011(2) -0.0015(17)
N2 0.035(3) 0.008(3) 0.041(3) -0.001(2) -0.008(2) 0.001(2)
N1 0.033(3) 0.011(3) 0.044(3) -0.003(2) -0.011(2) -0.001(2)
O4 0.045(3) 0.006(2) 0.059(3) 0.000(2) -0.021(2) 0.002(2)
O3 0.041(3) 0.014(3) 0.067(4) 0.004(2) -0.022(2) 0.000(2)
C1 0.033(4) 0.006(4) 0.041(4) 0.005(3) -0.003(3) 0.003(2)
C5 0.030(4) 0.014(4) 0.037(4) 0.001(3) -0.007(3) 0.004(3)
OW 0.068(4) 0.041(4) 0.089(5) 0.005(3) -0.018(3) -0.001(3)

_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 O2 1.904(5) 3_757 ?
Cu1 O2 1.904(5) . ?
Cu1 O1 1.939(5) . ?
Cu1 O1 1.939(5) 3_757 ?
C4 O4 1.202(8) . ?
C4 N1 1.376(8) . ?
C4 N2 1.384(7) . ?
C3 C2 1.336(8) . ?
C3 N2 1.345(8) . ?
C2 C1 1.433(8) . ?
C2 C5 1.498(8) . ?
O1 C1 1.272(7) . ?
O2 C5 1.289(7) . ?
N1 C1 1.378(8) . ?
O3 C5 1.252(7) . ?

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 Cu1 O2 180.000(1) 3_757 . ?
O2 Cu1 O1 86.37(15) 3_757 . ?
O2 Cu1 O1 93.63(15) . . ?
O2 Cu1 O1 93.63(15) 3_757 3_757 ?
O2 Cu1 O1 86.37(15) . 3_757 ?
O1 Cu1 O1 180.000(1) . 3_757 ?
O4 C4 N1 122.4(5) . . ?
O4 C4 N2 122.7(5) . . ?
N1 C4 N2 114.9(5) . . ?
C2 C3 N2 124.2(6) . . ?
C3 C2 C1 117.5(6) . . ?
C3 C2 C5 119.7(6) . . ?
C1 C2 C5 122.8(5) . . ?
C1 O1 Cu1 124.7(4) . . ?
C5 O2 Cu1 130.7(4) . . ?
C3 N2 C4 121.5(5) . . ?
C4 N1 C1 125.3(5) . . ?
O1 C1 N1 116.0(5) . . ?
O1 C1 C2 127.4(5) . . ?
N1 C1 C2 116.6(5) . . ?
O3 C5 O2 122.9(6) . . ?
O3 C5 C2 117.9(5) . . ?
O2 C5 C2 119.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        23.84
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         1.232
_refine_diff_density_min         -0.764
_refine_diff_density_rms         0.207
####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_compound2
_audit_block_doi                 10.5517/cc139xgs
_database_code_depnum_ccdc_archive 'CCDC 1022425'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C4QI00129J 2015
_audit_update_record             
;
2014-09-01 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H8 Mn N2 O7'
_chemical_formula_weight         263.07

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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                   5.2909(2)
_cell_length_b                   12.0901(5)
_cell_length_c                   13.9601(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.199(2)
_cell_angle_gamma                90.00
_cell_volume                     892.99(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2769
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      23.97

_exptl_crystal_description       'Square block'
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.957
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_absorpt_coefficient_mu    1.500
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7516
_exptl_absorpt_correction_T_max  0.9609
_exptl_absorpt_process_details   SADABS

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5162
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         28.95
_reflns_number_total             2106
_reflns_number_gt                1695
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker,2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 1.4.1'
_computing_publication_material  'PLATON (Spek, 2003)'

_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)+(0.0297P)²+0.9914P] 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         2106
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0826
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
C1 C 0.6646(5) 0.36045(19) 0.05944(16) 0.0194(5) Uani 1 1 d . . .
C2 C 0.9379(5) 0.36168(19) -0.08146(15) 0.0185(5) Uani 1 1 d . . .
C3 C 0.9352(5) 0.2149(2) 0.03274(16) 0.0209(5) Uani 1 1 d . . .
C4 C 1.0398(5) 0.25854(19) -0.04883(16) 0.0184(5) Uani 1 1 d . . .
C5 C 1.2487(5) 0.1987(2) -0.09802(16) 0.0205(5) Uani 1 1 d . . .
N1 N 0.7554(4) 0.26081(16) 0.08809(13) 0.0201(4) Uani 1 1 d . . .
N2 N 0.7563(4) 0.40583(17) -0.02327(14) 0.0221(5) Uani 1 1 d . . .
O1 O 0.9299(4) 0.04528(18) 0.22155(16) 0.0327(5) Uani 1 1 d . . .
O2 O 0.4071(4) 0.05214(16) 0.12851(13) 0.0235(4) Uani 1 1 d . . .
O3 O 0.2807(4) 0.27119(18) 0.22830(17) 0.0360(5) Uani 1 1 d . . .
O4 O 0.4971(4) 0.41210(14) 0.10456(12) 0.0275(4) Uani 1 1 d . . .
O5 O 0.9939(4) 0.41496(14) -0.15514(11) 0.0254(4) Uani 1 1 d . . .
O6 O 1.3521(4) 0.12037(16) -0.05434(12) 0.0318(5) Uani 1 1 d . . .
O7 O 1.3180(4) 0.22958(15) -0.18043(12) 0.0274(4) Uani 1 1 d . . .
Mn1 Mn 0.62285(7) 0.16870(3) 0.21843(2) 0.02077(12) Uani 1 1 d . . .
H1 H 0.936(7) 0.012(3) 0.260(3) 0.045(12) Uiso 1 1 d . . .
H2 H 1.087(7) 0.047(3) 0.192(2) 0.051(10) Uiso 1 1 d . . .
H3 H 0.487(7) -0.002(3) 0.114(2) 0.041(10) Uiso 1 1 d . . .
H4 H 0.384(7) 0.080(3) 0.073(3) 0.048(10) Uiso 1 1 d . . .
H5 H 0.156(6) 0.275(2) 0.260(2) 0.029(8) Uiso 1 1 d . . .
H6 H 0.306(8) 0.323(3) 0.198(3) 0.065(13) Uiso 1 1 d . . .
H7 H 0.986(5) 0.141(2) 0.0519(19) 0.028(7) Uiso 1 1 d . . .
H8 H 0.690(6) 0.464(3) -0.045(2) 0.033(8) 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
C1 0.0219(13) 0.0202(11) 0.0161(10) 0.0016(9) 0.0057(9) 0.0018(10)
C2 0.0210(13) 0.0193(11) 0.0151(10) -0.0014(8) 0.0046(9) 0.0013(10)
C3 0.0232(14) 0.0221(12) 0.0176(11) 0.0037(9) 0.0059(10) 0.0063(10)
C4 0.0192(13) 0.0200(11) 0.0161(10) 0.0010(9) 0.0031(9) 0.0054(9)
C5 0.0215(13) 0.0238(12) 0.0161(10) -0.0024(9) 0.0042(10) 0.0032(10)
N1 0.0224(11) 0.0217(10) 0.0163(9) 0.0035(8) 0.0071(8) 0.0059(9)
N2 0.0280(12) 0.0185(10) 0.0198(10) 0.0053(8) 0.0105(9) 0.0083(9)
O1 0.0282(12) 0.0377(12) 0.0321(11) 0.0127(9) 0.0083(9) 0.0080(9)
O2 0.0279(11) 0.0235(9) 0.0189(9) -0.0022(7) 0.0031(8) 0.0076(8)
O3 0.0263(12) 0.0345(12) 0.0472(13) 0.0132(10) 0.0188(10) 0.0056(9)
O4 0.0311(11) 0.0255(9) 0.0261(9) 0.0044(7) 0.0167(8) 0.0093(8)
O5 0.0353(11) 0.0222(9) 0.0187(8) 0.0047(6) 0.0130(7) 0.0072(8)
O6 0.0414(12) 0.0345(10) 0.0197(8) 0.0051(8) 0.0071(8) 0.0230(9)
O7 0.0266(11) 0.0352(10) 0.0206(8) 0.0065(7) 0.0111(8) 0.0107(8)
Mn1 0.0225(2) 0.0245(2) 0.01536(18) -0.00033(14) 0.00655(14) -0.00115(16)

_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 O4 1.256(3) . ?
C1 N1 1.357(3) . ?
C1 N2 1.369(3) . ?
C2 O5 1.250(3) . ?
C2 N2 1.369(3) . ?
C2 C4 1.432(3) . ?
C3 N1 1.347(3) . ?
C3 C4 1.373(3) . ?
C4 C5 1.491(3) . ?
C5 O6 1.251(3) . ?
C5 O7 1.265(3) . ?
N1 Mn1 2.2476(19) . ?
O1 Mn1 2.206(2) . ?
O2 Mn1 2.2033(19) . ?
O3 Mn1 2.198(2) . ?
O5 Mn1 2.1475(16) 4_665 ?
O7 Mn1 2.1359(18) 4_665 ?
Mn1 O7 2.1359(18) 4_566 ?
Mn1 O5 2.1475(16) 4_566 ?

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
O4 C1 N1 122.9(2) . . ?
O4 C1 N2 118.5(2) . . ?
N1 C1 N2 118.6(2) . . ?
O5 C2 N2 117.1(2) . . ?
O5 C2 C4 128.4(2) . . ?
N2 C2 C4 114.51(19) . . ?
N1 C3 C4 127.2(2) . . ?
C3 C4 C2 116.5(2) . . ?
C3 C4 C5 119.8(2) . . ?
C2 C4 C5 123.7(2) . . ?
O6 C5 O7 122.6(2) . . ?
O6 C5 C4 117.8(2) . . ?
O7 C5 C4 119.6(2) . . ?
C3 N1 C1 116.51(19) . . ?
C3 N1 Mn1 118.91(15) . . ?
C1 N1 Mn1 124.57(15) . . ?
C1 N2 C2 126.6(2) . . ?
C2 O5 Mn1 120.69(15) . 4_665 ?
C5 O7 Mn1 129.05(16) . 4_665 ?
O7 Mn1 O5 83.23(7) 4_566 4_566 ?
O7 Mn1 O3 91.73(8) 4_566 . ?
O5 Mn1 O3 87.13(8) 4_566 . ?
O7 Mn1 O2 173.30(7) 4_566 . ?
O5 Mn1 O2 90.09(7) 4_566 . ?
O3 Mn1 O2 88.35(8) . . ?
O7 Mn1 O1 91.27(8) 4_566 . ?
O5 Mn1 O1 84.33(8) 4_566 . ?
O3 Mn1 O1 170.56(8) . . ?
O2 Mn1 O1 87.63(8) . . ?
O7 Mn1 N1 95.64(7) 4_566 . ?
O5 Mn1 N1 178.40(7) 4_566 . ?
O3 Mn1 N1 91.76(8) . . ?
O2 Mn1 N1 91.04(7) . . ?
O1 Mn1 N1 96.85(8) . . ?

_diffrn_measured_fraction_theta_max 0.895
_diffrn_reflns_theta_full        28.95
_diffrn_measured_fraction_theta_full 0.895
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_compound3
_audit_block_doi                 10.5517/cc139xht
_database_code_depnum_ccdc_archive 'CCDC 1022426'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C4QI00129J 2015
_audit_update_record             
;
2014-11-11 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Compound 3'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H5 Mn N2 O6'
_chemical_formula_weight         244.05

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   12.9385(3)
_cell_length_b                   6.73100(10)
_cell_length_c                   17.0240(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1482.60(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2795
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       cubic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    1.789
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9003
_exptl_absorpt_correction_T_max  0.9003
_exptl_absorpt_process_details   SADABS

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8983
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         22.18
_reflns_number_total             930
_reflns_number_gt                843
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART (Bruker,2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 1.4.1'
_computing_publication_material  'PLATON (Spek, 2003)'

_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)+(0.0677P)²+0.3436P] 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         930
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   1.328
_refine_ls_restrained_S_all      1.328
_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
C1 C 0.5963(3) 0.2102(5) 0.7228(2) 0.0181(10) Uani 1 1 d . . .
C2 C 0.1911(3) 0.2544(5) 0.3255(2) 0.0142(9) Uani 1 1 d . . .
C3 C 0.6897(3) 0.2987(5) 0.5920(2) 0.0153(10) Uani 1 1 d . . .
C4 C 0.3685(3) 0.1765(5) 0.4095(2) 0.0166(10) Uani 1 1 d . . .
C5 C 0.2860(3) 0.2710(6) 0.2921(2) 0.0171(9) Uani 1 1 d . . .
H5 H 0.2904 0.3064 0.2394 0.021 Uiso 1 1 calc R . .
N1 N 0.2786(2) 0.1595(4) 0.44615(19) 0.0167(8) Uani 1 1 d . . .
N2 N 0.3738(2) 0.2382(4) 0.33231(18) 0.0189(8) Uani 1 1 d . . .
O1W O 0.33106(19) 0.0073(4) 0.61331(16) 0.0274(7) Uani 1 1 d . . .
H1O1 H 0.2906 -0.0038 0.5750 0.033 Uiso 1 1 d R . .
H2O1 H 0.3424 -0.1175 0.6433 0.033 Uiso 1 1 d R . .
O2W O 0.3839(2) 0.4554(4) 0.57626(14) 0.0224(7) Uani 1 1 d . . .
H1O2 H 0.3863 0.5108 0.5300 0.027 Uiso 1 1 d R . .
H2O2 H 0.3978 0.5290 0.6189 0.027 Uiso 1 1 d R . .
O3 O 0.5101(2) 0.1861(4) 0.69088(17) 0.0266(8) Uani 1 1 d . . .
O4 O 0.6074(2) 0.2022(4) 0.79595(16) 0.0263(8) Uani 1 1 d . . .
O5 O 0.6058(2) 0.3148(4) 0.55305(17) 0.0231(8) Uani 1 1 d . . .
O6 O 0.4544(2) 0.1370(4) 0.44380(17) 0.0205(7) Uani 1 1 d . . .
Mn1 Mn 0.46137(4) 0.16786(9) 0.57167(3) 0.0190(4) 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
C1 0.023(3) 0.0149(19) 0.017(3) -0.0007(17) 0.002(2) 0.0016(18)
C2 0.019(2) 0.013(2) 0.011(2) 0.0005(17) -0.0023(18) 0.0013(15)
C3 0.017(3) 0.013(2) 0.016(2) -0.0003(16) -0.003(2) -0.0012(16)
C4 0.020(3) 0.012(2) 0.017(2) -0.0039(15) -0.003(2) 0.0006(16)
C5 0.026(3) 0.017(2) 0.008(2) 0.0021(15) 0.0006(19) 0.0022(18)
N1 0.015(2) 0.0203(19) 0.0150(18) 0.0025(13) 0.0009(16) 0.0038(13)
N2 0.021(2) 0.0185(18) 0.0169(19) 0.0032(15) -0.0008(16) 0.0007(14)
O1W 0.0198(15) 0.0354(17) 0.0270(17) 0.0078(13) -0.0047(13) -0.0038(14)
O2W 0.0297(18) 0.0251(16) 0.0125(15) -0.0002(11) 0.0001(12) 0.0029(13)
O3 0.0173(18) 0.0446(19) 0.0177(17) 0.0004(12) 0.0026(15) -0.0033(14)
O4 0.0341(19) 0.0333(16) 0.0114(18) 0.0007(12) 0.0008(14) -0.0059(13)
O5 0.0157(17) 0.0336(18) 0.0199(17) 0.0077(11) -0.0004(14) -0.0026(12)
O6 0.0166(18) 0.0251(16) 0.0196(16) -0.0012(12) -0.0044(13) 0.0050(11)
Mn1 0.0168(5) 0.0236(5) 0.0165(5) 0.0004(2) 0.0010(3) 0.0011(2)

_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
C1 O3 1.252(5) . ?
C1 O4 1.254(5) . ?
C1 C2 1.496(5) 3_556 ?
C2 C5 1.357(5) . ?
C2 C3 1.449(6) 3_456 ?
C2 C1 1.496(5) 3_456 ?
C3 O5 1.276(4) . ?
C3 N1 1.351(5) 3_556 ?
C3 C2 1.449(6) 3_556 ?
C4 O6 1.284(5) . ?
C4 N1 1.326(5) . ?
C4 N2 1.379(5) . ?
C5 N2 1.345(5) . ?
N1 C3 1.351(5) 3_456 ?
O1W Mn1 2.125(3) . ?
O2W Mn1 2.181(3) . ?
O3 Mn1 2.128(3) . ?
O5 Mn1 2.138(3) . ?
O6 Mn1 2.188(3) . ?
O6 Mn1 2.338(3) 5_656 ?
Mn1 O6 2.338(3) 5_656 ?

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
O3 C1 O4 121.8(4) . . ?
O3 C1 C2 120.8(4) . 3_556 ?
O4 C1 C2 117.3(4) . 3_556 ?
C5 C2 C3 116.0(3) . 3_456 ?
C5 C2 C1 119.9(3) . 3_456 ?
C3 C2 C1 124.2(3) 3_456 3_456 ?
O5 C3 N1 117.1(3) . 3_556 ?
O5 C3 C2 122.4(3) . 3_556 ?
N1 C3 C2 120.4(3) 3_556 3_556 ?
O6 C4 N1 121.8(4) . . ?
O6 C4 N2 117.0(4) . . ?
N1 C4 N2 121.2(4) . . ?
N2 C5 C2 122.5(3) . . ?
C4 N1 C3 120.2(3) . 3_456 ?
C5 N2 C4 119.6(3) . . ?
C1 O3 Mn1 133.3(3) . . ?
C3 O5 Mn1 128.8(2) . . ?
C4 O6 Mn1 118.0(2) . . ?
C4 O6 Mn1 122.3(2) . 5_656 ?
Mn1 O6 Mn1 100.15(11) . 5_656 ?
O1W Mn1 O3 86.91(11) . . ?
O1W Mn1 O5 168.09(11) . . ?
O3 Mn1 O5 81.72(11) . . ?
O1W Mn1 O2W 94.29(10) . . ?
O3 Mn1 O2W 92.90(10) . . ?
O5 Mn1 O2W 89.81(10) . . ?
O1W Mn1 O6 104.54(11) . . ?
O3 Mn1 O6 165.01(11) . . ?
O5 Mn1 O6 86.12(11) . . ?
O2W Mn1 O6 95.80(9) . . ?
O1W Mn1 O6 87.75(10) . 5_656 ?
O3 Mn1 O6 91.15(10) . 5_656 ?
O5 Mn1 O6 88.96(10) . 5_656 ?
O2W Mn1 O6 175.55(10) . 5_656 ?
O6 Mn1 O6 79.85(11) . 5_656 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        22.18
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.126
####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_compound4
_audit_block_doi                 10.5517/cc139xjv
_database_code_depnum_ccdc_archive 'CCDC 1022427'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C4QI00129J 2015
_audit_update_record             
;
2015-03-02 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 Cu N3 O7'
_chemical_formula_weight         348.76

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   P21/n

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                   14.154(3)
_cell_length_b                   6.6209(13)
_cell_length_c                   15.047(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.39(3)
_cell_angle_gamma                90.00
_cell_volume                     1252.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708
_exptl_absorpt_coefficient_mu    1.785
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8558
_exptl_absorpt_correction_T_max  0.9652
_exptl_absorpt_process_details   SADABS

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10533
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         31.16
_reflns_number_total             3547
_reflns_number_gt                2946
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART (Bruker,2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 1.4.1'
_computing_publication_material  'PLATON (Spek, 2003)'

_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)+(0.1246P)²+6.5337P] 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         3547
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0869
_refine_ls_wR_factor_ref         0.2402
_refine_ls_wR_factor_gt          0.2256
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
C1 C 0.9643(4) 0.0863(8) 0.1837(4) 0.0234(10) Uani 1 1 d . . .
H1 H 0.9693 0.0267 0.2417 0.028 Uiso 1 1 calc R . .
C2 C 0.9193(4) 0.3595(8) 0.0773(4) 0.0207(9) Uani 1 1 d . . .
H2 H 0.8943 0.4913 0.0617 0.025 Uiso 1 1 calc R . .
C3 C 0.9454(4) 0.2577(8) 0.0122(4) 0.0220(10) Uani 1 1 d . . .
H3 H 0.9368 0.3203 -0.0463 0.026 Uiso 1 1 calc R . .
C4 C 0.9941(4) -0.0249(9) 0.1233(4) 0.0249(10) Uani 1 1 d . . .
H4 H 1.0201 -0.1553 0.1417 0.030 Uiso 1 1 calc R . .
C5 C 0.9850(4) 0.0590(7) 0.0335(3) 0.0167(9) Uani 1 1 d . . .
C6 C 0.7818(4) 0.2607(8) 0.3413(3) 0.0184(9) Uani 1 1 d . . .
C7 C 0.8259(3) 0.4530(7) 0.4033(4) 0.0176(9) Uani 1 1 d . . .
C9 C 0.8381(4) 0.7047(8) 0.5231(3) 0.0188(9) Uani 1 1 d . . .
N3 N 0.9063(3) 0.8023(7) 0.4960(3) 0.0197(8) Uani 1 1 d . . .
C11 C 0.9348(3) 0.7343(7) 0.4252(3) 0.0169(8) Uani 1 1 d . . .
N1 N 0.9282(3) 0.2776(6) 0.1626(3) 0.0184(8) Uani 1 1 d . . .
N2 N 0.8942(3) 0.5564(6) 0.3790(3) 0.0161(8) Uani 1 1 d . . .
C10 C 0.7969(4) 0.5155(9) 0.4729(4) 0.0212(9) Uani 1 1 d . . .
H10 H 0.7514 0.4379 0.4880 0.025 Uiso 1 1 calc R . .
O1 O 0.8144(3) 0.2273(6) 0.2758(2) 0.0202(7) Uani 1 1 d . . .
O2 O 0.7178(3) 0.1560(6) 0.3559(3) 0.0220(7) Uani 1 1 d . . .
O1W O 1.0177(3) 0.6257(6) 0.2730(3) 0.0207(7) Uani 1 1 d . . .
H1W H 1.0255 0.7236 0.3130 0.025 Uiso 1 1 d R . .
H2W H 1.0935 0.5768 0.2983 0.025 Uiso 1 1 d R . .
O3 O 0.9991(3) 0.8390(6) 0.4076(3) 0.0220(7) Uani 1 1 d . . .
O2W O 1.2118(3) 0.5107(6) 0.3031(3) 0.0267(8) Uani 1 1 d . . .
H3W H 1.2206 0.4074 0.3599 0.032 Uiso 1 1 d R . .
H4W H 1.2095 0.4436 0.2464 0.032 Uiso 1 1 d R . .
O4 O 0.8191(3) 0.7814(6) 0.5896(3) 0.0245(8) Uani 1 1 d . . .
O3W O 0.7178(3) 1.1029(7) 0.6325(3) 0.0287(8) Uani 1 1 d . . .
H5W H 0.7420 1.0217 0.5963 0.034 Uiso 1 1 d R . .
H6W H 0.7560 1.1052 0.7035 0.034 Uiso 1 1 d R . .
Cu1 Cu 0.90162(4) 0.44014(9) 0.26041(4) 0.0175(2) 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
C1 0.026(2) 0.024(3) 0.015(2) -0.0007(18) 0.0052(18) 0.0050(19)
C2 0.018(2) 0.019(2) 0.018(2) 0.0009(18) 0.0027(17) 0.0022(17)
C3 0.020(2) 0.022(3) 0.018(2) 0.0008(19) 0.0034(17) 0.0055(17)
C4 0.029(3) 0.020(2) 0.023(2) -0.001(2) 0.010(2) 0.002(2)
C5 0.018(2) 0.013(2) 0.0150(19) -0.0023(16) 0.0038(16) 0.0002(15)
C6 0.0153(19) 0.017(2) 0.0152(19) 0.0000(17) 0.0004(16) -0.0034(16)
C7 0.0096(17) 0.016(2) 0.017(2) -0.0025(16) -0.0031(15) -0.0015(15)
C9 0.019(2) 0.018(2) 0.0126(18) 0.0023(17) 0.0014(16) 0.0000(17)
N3 0.0186(18) 0.019(2) 0.0174(17) -0.0016(15) 0.0048(15) -0.0020(15)
C11 0.0143(18) 0.019(2) 0.0125(18) 0.0025(17) 0.0017(15) 0.0026(16)
N1 0.0161(17) 0.019(2) 0.0148(16) -0.0010(15) 0.0027(14) -0.0024(15)
N2 0.0111(16) 0.018(2) 0.0129(16) -0.0021(14) 0.0004(13) 0.0018(13)
C10 0.0141(19) 0.024(3) 0.018(2) -0.0022(19) 0.0010(16) -0.0020(18)
O1 0.0192(15) 0.0207(18) 0.0160(15) -0.0028(13) 0.0041(13) -0.0048(13)
O2 0.0210(16) 0.0232(19) 0.0172(15) -0.0031(14) 0.0050(13) -0.0068(14)
O1W 0.0200(16) 0.0173(18) 0.0208(16) -0.0027(14) 0.0060(13) -0.0030(13)
O3 0.0226(16) 0.0202(18) 0.0203(16) -0.0062(14) 0.0072(13) -0.0064(14)
O2W 0.0293(19) 0.024(2) 0.0283(19) 0.0003(16) 0.0143(16) 0.0026(16)
O4 0.0258(18) 0.0246(19) 0.0202(16) -0.0045(15) 0.0082(14) -0.0030(15)
O3W 0.030(2) 0.030(2) 0.0228(18) -0.0076(16) 0.0093(16) -0.0038(16)
Cu1 0.0163(3) 0.0168(4) 0.0129(3) -0.0016(2) 0.0013(2) -0.0007(2)

_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
C1 N1 1.348(7) . ?
C1 C4 1.378(7) . ?
C1 H1 0.9300 . ?
C2 N1 1.345(6) . ?
C2 C3 1.372(7) . ?
C2 H2 0.9300 . ?
C3 C5 1.408(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.411(7) . ?
C4 H4 0.9300 . ?
C5 C5 1.484(9) 3_755 ?
C6 O2 1.238(6) . ?
C6 O1 1.285(6) . ?
C6 C7 1.531(7) . ?
C7 C10 1.354(7) . ?
C7 N2 1.366(6) . ?
C9 O4 1.257(6) . ?
C9 N3 1.369(6) . ?
C9 C10 1.440(7) . ?
N3 C11 1.378(6) . ?
C11 O3 1.265(6) . ?
C11 N2 1.354(6) . ?
N1 Cu1 1.994(4) . ?
N2 Cu1 1.990(4) . ?
C10 H10 0.9300 . ?
O1 Cu1 1.956(4) . ?
O2 Cu1 2.290(4) 2_645 ?
O1W Cu1 1.990(4) . ?
O1W H1W 0.8570 . ?
O1W H2W 1.0121 . ?
O2W H3W 1.0565 . ?
O2W H4W 0.9489 . ?
O3W H5W 0.9363 . ?
O3W H6W 0.9494 . ?
Cu1 O2 2.290(4) 2_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C4 123.0(5) . . ?
N1 C1 H1 118.5 . . ?
C4 C1 H1 118.5 . . ?
N1 C2 C3 123.0(5) . . ?
N1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
C2 C3 C5 120.4(5) . . ?
C2 C3 H3 119.8 . . ?
C5 C3 H3 119.8 . . ?
C1 C4 C5 120.1(5) . . ?
C1 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C5 C4 115.9(4) . . ?
C3 C5 C5 123.1(5) . 3_755 ?
C4 C5 C5 121.0(5) . 3_755 ?
O2 C6 O1 126.2(5) . . ?
O2 C6 C7 118.9(4) . . ?
O1 C6 C7 114.9(4) . . ?
C10 C7 N2 123.9(4) . . ?
C10 C7 C6 122.8(5) . . ?
N2 C7 C6 113.2(4) . . ?
O4 C9 N3 118.9(5) . . ?
O4 C9 C10 125.8(5) . . ?
N3 C9 C10 115.2(4) . . ?
C9 N3 C11 125.0(4) . . ?
O3 C11 N2 123.0(4) . . ?
O3 C11 N3 118.6(4) . . ?
N2 C11 N3 118.4(4) . . ?
C2 N1 C1 117.6(4) . . ?
C2 N1 Cu1 121.4(3) . . ?
C1 N1 Cu1 120.9(3) . . ?
C11 N2 C7 119.0(4) . . ?
C11 N2 Cu1 127.8(3) . . ?
C7 N2 Cu1 112.5(3) . . ?
C7 C10 C9 118.5(5) . . ?
C7 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C6 O1 Cu1 115.8(3) . . ?
C6 O2 Cu1 123.8(3) . 2_645 ?
Cu1 O1W H1W 111.5 . . ?
Cu1 O1W H2W 121.6 . . ?
H1W O1W H2W 101.9 . . ?
H3W O2W H4W 111.5 . . ?
H5W O3W H6W 119.5 . . ?
O1 Cu1 N2 82.89(16) . . ?
O1 Cu1 O1W 166.43(15) . . ?
N2 Cu1 O1W 93.30(16) . . ?
O1 Cu1 N1 92.43(16) . . ?
N2 Cu1 N1 167.53(17) . . ?
O1W Cu1 N1 88.59(16) . . ?
O1 Cu1 O2 104.83(14) . 2_655 ?
N2 Cu1 O2 96.84(15) . 2_655 ?
O1W Cu1 O2 88.53(14) . 2_655 ?
N1 Cu1 O2 95.53(15) . 2_655 ?

_diffrn_measured_fraction_theta_max 0.876
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.751
_refine_diff_density_min         -1.522
_refine_diff_density_rms         0.205
####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_compound5
_audit_block_doi                 10.5517/cc139xkw
_database_code_depnum_ccdc_archive 'CCDC 1022428'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C4QI00129J 2015
_audit_update_record             
;
2014-09-01 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H13 N5 Ni O5'
_chemical_formula_weight         462.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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/n

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

_cell_length_a                   10.3949(2)
_cell_length_b                   11.3275(2)
_cell_length_c                   18.6129(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.9990(10)
_cell_angle_gamma                90.00
_cell_volume                     2135.47(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2921
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      25.81

_exptl_crystal_description       'Square block'
_exptl_crystal_colour            'Light green'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8059
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_process_details   SADABS

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16479
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.70
_reflns_number_total             4069
_reflns_number_gt                3449
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker,2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 1.4.1'
_computing_publication_material  'PLATON (Spek, 2003)'

_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)+(0.0375P)²+1.2106P] 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         4069
_refine_ls_number_parameters     285
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0881
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Ni1 Ni 0.2500 0.28913(3) 0.7500 0.01878(12) Uani 1 2 d S . .
Ni2 Ni 0.7500 0.32594(3) 0.7500 0.01873(12) Uani 1 2 d S . .
N1 N 0.14726(19) 0.4139(2) 0.54091(11) 0.0340(5) Uani 1 1 d . . .
N2 N 0.3239(2) 0.4816(2) 0.49319(13) 0.0477(7) Uani 1 1 d . . .
N3 N 0.2500 0.4793(2) 0.7500 0.0304(7) Uani 1 2 d S . .
N4 N 0.2500 1.1035(2) 0.7500 0.0299(7) Uani 1 2 d S . .
N5 N 0.7500 0.5133(2) 0.7500 0.0283(7) Uani 1 2 d S . .
N6 N 0.7500 1.1410(2) 0.7500 0.0264(6) Uani 1 2 d S . .
O1 O 0.16508(16) 0.30042(14) 0.64125(9) 0.0263(4) Uani 1 1 d . . .
O2 O 0.43007(14) 0.28674(13) 0.72698(9) 0.0234(4) Uani 1 1 d . . .
O3 O 0.58274(15) 0.33074(14) 0.66603(9) 0.0255(4) Uani 1 1 d . . .
O4 O 0.64798(16) 0.31593(15) 0.83438(9) 0.0277(4) Uani 1 1 d . . .
O5 O 0.11177(19) 0.5352(2) 0.44261(12) 0.0572(6) Uani 1 1 d . . .
C1 C 0.4642(2) 0.32392(19) 0.66946(13) 0.0214(5) Uani 1 1 d . . .
C2 C 0.3624(2) 0.3657(2) 0.60610(13) 0.0265(5) Uani 1 1 d . . .
C3 C 0.2243(2) 0.3555(2) 0.60022(13) 0.0231(5) Uani 1 1 d . . .
C4 C 0.1932(3) 0.4801(3) 0.48998(15) 0.0386(7) Uani 1 1 d . . .
C5 C 0.4004(3) 0.4275(3) 0.54966(15) 0.0381(7) Uani 1 1 d . . .
H5 H 0.4906 0.4310 0.5521 0.046 Uiso 1 1 calc R . .
C6 C 0.1421(3) 0.5405(2) 0.71978(17) 0.0438(7) Uani 1 1 d . . .
H6 H 0.0660 0.4991 0.6981 0.053 Uiso 1 1 calc R . .
C7 C 0.1377(3) 0.6613(2) 0.7190(2) 0.0547(9) Uani 1 1 d . . .
H7 H 0.0594 0.6998 0.6977 0.066 Uiso 1 1 calc R . .
C8 C 0.2500 0.7268(3) 0.7500 0.0436(11) Uani 1 2 d S . .
C9 C 0.2500 0.8568(3) 0.7500 0.0482(11) Uani 1 2 d S . .
C10 C 0.3639(3) 0.9206(3) 0.7571(3) 0.0776(13) Uani 1 1 d . . .
H10 H 0.4446 0.8820 0.7633 0.093 Uiso 1 1 calc R . .
C11 C 0.3589(3) 1.0408(3) 0.7552(3) 0.0720(12) Uani 1 1 d . . .
H11 H 0.4375 1.0815 0.7577 0.086 Uiso 1 1 calc R . .
C12 C 0.7937(3) 0.5742(2) 0.81159(16) 0.0421(7) Uani 1 1 d . . .
H12 H 0.8234 0.5332 0.8554 0.051 Uiso 1 1 calc R . .
C13 C 0.7967(3) 0.6968(2) 0.81320(16) 0.0460(8) Uani 1 1 d . . .
H13 H 0.8305 0.7359 0.8573 0.055 Uiso 1 1 calc R . .
C14 C 0.7500 0.7602(3) 0.7500 0.0310(8) Uani 1 2 d S . .
C15 C 0.7500 0.8930(3) 0.7500 0.0310(8) Uani 1 2 d S . .
C16 C 0.7825(4) 0.9577(2) 0.81374(17) 0.0551(9) Uani 1 1 d . . .
H16 H 0.8053 0.9192 0.8589 0.066 Uiso 1 1 calc R . .
C17 C 0.7817(3) 1.0785(2) 0.81148(16) 0.0470(8) Uani 1 1 d . . .
H17 H 0.8048 1.1191 0.8559 0.056 Uiso 1 1 calc R . .
C18 C 0.0681(3) 0.9750(7) 0.5131(4) 0.142(3) Uani 1 1 d D . .
C19 C 0.0973(9) 0.8606(7) 0.4961(4) 0.148(3) Uani 1 1 d . . .
H19 H 0.0300 0.8106 0.4726 0.177 Uiso 1 1 calc R . .
C20 C 0.2293(10) 0.8193(6) 0.5143(4) 0.140(3) Uani 1 1 d . . .
H20 H 0.2499 0.7422 0.5040 0.168 Uiso 1 1 calc R . .
N7 N 0.3255(7) 0.8967(7) 0.5477(4) 0.154(2) Uani 1 1 d . . .
C21 C 0.2995(9) 1.0110(8) 0.5639(4) 0.150(3) Uani 1 1 d . . .
H21 H 0.3678 1.0616 0.5854 0.180 Uiso 1 1 calc R . .
C22 C 0.1686(9) 1.0505(7) 0.5474(4) 0.145(3) Uani 1 1 d . . .
H22 H 0.1490 1.1271 0.5594 0.174 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
Ni1 0.0167(2) 0.0146(2) 0.0248(2) 0.000 0.00418(17) 0.000
Ni2 0.0171(2) 0.0144(2) 0.0240(2) 0.000 0.00329(17) 0.000
N1 0.0197(10) 0.0506(15) 0.0312(12) 0.0163(10) 0.0044(9) 0.0011(9)
N2 0.0269(13) 0.0751(19) 0.0406(14) 0.0285(13) 0.0062(11) 0.0017(12)
N3 0.0248(15) 0.0185(15) 0.0468(19) 0.000 0.0057(14) 0.000
N4 0.0270(15) 0.0156(15) 0.0466(19) 0.000 0.0074(14) 0.000
N5 0.0299(16) 0.0208(15) 0.0328(17) 0.000 0.0041(13) 0.000
N6 0.0331(16) 0.0194(15) 0.0253(16) 0.000 0.0035(13) 0.000
O1 0.0213(8) 0.0293(9) 0.0270(9) 0.0055(7) 0.0025(7) -0.0059(7)
O2 0.0159(8) 0.0253(9) 0.0284(9) 0.0042(7) 0.0038(7) -0.0006(6)
O3 0.0170(8) 0.0311(10) 0.0286(9) 0.0016(7) 0.0052(7) 0.0005(7)
O4 0.0218(9) 0.0366(10) 0.0258(9) -0.0030(7) 0.0076(7) 0.0004(7)
O5 0.0294(11) 0.0898(18) 0.0522(13) 0.0407(12) 0.0085(10) 0.0085(11)
C1 0.0201(12) 0.0155(12) 0.0287(13) -0.0017(9) 0.0059(10) -0.0015(9)
C2 0.0193(12) 0.0322(14) 0.0261(13) 0.0029(10) 0.0011(10) 0.0012(10)
C3 0.0188(11) 0.0251(13) 0.0244(12) -0.0003(10) 0.0029(10) -0.0035(9)
C4 0.0238(14) 0.0564(19) 0.0346(15) 0.0200(13) 0.0049(11) 0.0005(12)
C5 0.0213(13) 0.0599(19) 0.0340(15) 0.0164(13) 0.0078(11) -0.0010(12)
C6 0.0333(15) 0.0163(14) 0.075(2) 0.0014(13) -0.0024(14) -0.0005(11)
C7 0.0360(17) 0.0221(16) 0.101(3) 0.0066(16) 0.0038(17) 0.0027(12)
C8 0.031(2) 0.016(2) 0.083(3) 0.000 0.011(2) 0.000
C9 0.048(3) 0.017(2) 0.081(3) 0.000 0.016(2) 0.000
C10 0.0355(18) 0.0196(17) 0.180(4) 0.013(2) 0.028(2) 0.0054(13)
C11 0.0330(17) 0.0184(16) 0.167(4) 0.0059(19) 0.028(2) -0.0014(12)
C12 0.066(2) 0.0186(14) 0.0358(16) 0.0016(11) -0.0015(14) -0.0001(13)
C13 0.073(2) 0.0217(15) 0.0356(17) -0.0054(12) -0.0048(15) 0.0004(13)
C14 0.045(2) 0.0124(17) 0.034(2) 0.000 0.0067(17) 0.000
C15 0.038(2) 0.0136(18) 0.041(2) 0.000 0.0075(17) 0.000
C16 0.101(3) 0.0208(16) 0.0372(17) 0.0045(12) 0.0011(17) -0.0006(16)
C17 0.079(2) 0.0258(16) 0.0286(16) -0.0022(12) -0.0041(15) 0.0039(14)
C18 0.201(9) 0.115(6) 0.115(6) -0.024(4) 0.045(6) -0.027(6)
C19 0.154(7) 0.137(7) 0.151(7) -0.013(5) 0.031(6) -0.016(5)
C20 0.198(9) 0.107(5) 0.113(5) -0.003(4) 0.030(5) -0.003(6)
N7 0.175(6) 0.142(6) 0.144(5) -0.013(4) 0.035(4) -0.011(5)
C21 0.156(7) 0.151(8) 0.142(6) -0.003(6) 0.031(6) -0.030(6)
C22 0.192(8) 0.110(5) 0.128(6) -0.019(4) 0.025(6) -0.015(6)

_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
Ni1 O2 2.0122(15) . ?
Ni1 O2 2.0122(15) 2_556 ?
Ni1 O1 2.0222(16) . ?
Ni1 O1 2.0222(16) 2_556 ?
Ni1 N4 2.103(3) 1_545 ?
Ni1 N3 2.155(3) . ?
Ni2 O3 2.0606(16) . ?
Ni2 O3 2.0606(16) 2_656 ?
Ni2 O4 2.0865(15) 2_656 ?
Ni2 O4 2.0865(15) . ?
Ni2 N6 2.095(3) 1_545 ?
Ni2 N5 2.122(3) . ?
N1 C4 1.376(3) . ?
N1 C3 1.378(3) . ?
N2 C5 1.318(3) . ?
N2 C4 1.346(4) . ?
N3 C6 1.330(3) 2_556 ?
N3 C6 1.330(3) . ?
N4 C11 1.321(3) 2_556 ?
N4 C11 1.321(3) . ?
N4 Ni1 2.103(3) 1_565 ?
N5 C12 1.328(3) . ?
N5 C12 1.328(3) 2_656 ?
N6 C17 1.323(3) 2_656 ?
N6 C17 1.323(3) . ?
N6 Ni2 2.095(3) 1_565 ?
O1 C3 1.250(3) . ?
O2 C1 1.273(3) . ?
O3 C1 1.251(3) . ?
O5 C4 1.244(3) . ?
C1 C2 1.474(3) . ?
C2 C5 1.391(3) . ?
C2 C3 1.420(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.395(3) . ?
C7 H7 0.9300 . ?
C8 C7 1.395(3) 2_556 ?
C8 C9 1.473(5) . ?
C9 C10 1.367(4) . ?
C9 C10 1.367(4) 2_556 ?
C10 C11 1.363(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.389(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(3) . ?
C13 H13 0.9300 . ?
C14 C13 1.371(3) 2_656 ?
C14 C15 1.505(5) . ?
C15 C16 1.370(3) . ?
C15 C16 1.370(3) 2_656 ?
C16 C17 1.369(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.384(9) . ?
C18 C22 1.391(9) . ?
C18 C18 1.5003(10) 3_576 ?
C19 C20 1.416(10) . ?
C19 H19 0.9300 . ?
C20 N7 1.370(9) . ?
C20 H20 0.9300 . ?
N7 C21 1.369(9) . ?
C21 C22 1.399(9) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Ni1 O2 178.46(9) . 2_556 ?
O2 Ni1 O1 90.30(6) . . ?
O2 Ni1 O1 89.80(6) 2_556 . ?
O2 Ni1 O1 89.80(6) . 2_556 ?
O2 Ni1 O1 90.30(6) 2_556 2_556 ?
O1 Ni1 O1 172.75(9) . 2_556 ?
O2 Ni1 N4 89.23(4) . 1_545 ?
O2 Ni1 N4 89.23(4) 2_556 1_545 ?
O1 Ni1 N4 93.63(5) . 1_545 ?
O1 Ni1 N4 93.63(5) 2_556 1_545 ?
O2 Ni1 N3 90.77(4) . . ?
O2 Ni1 N3 90.77(4) 2_556 . ?
O1 Ni1 N3 86.37(5) . . ?
O1 Ni1 N3 86.37(5) 2_556 . ?
N4 Ni1 N3 180.000(1) 1_545 . ?
O3 Ni2 O3 176.98(9) . 2_656 ?
O3 Ni2 O4 85.15(6) . 2_656 ?
O3 Ni2 O4 95.01(6) 2_656 2_656 ?
O3 Ni2 O4 95.01(6) . . ?
O3 Ni2 O4 85.15(6) 2_656 . ?
O4 Ni2 O4 173.77(9) 2_656 . ?
O3 Ni2 N6 91.51(5) . 1_545 ?
O3 Ni2 N6 91.51(5) 2_656 1_545 ?
O4 Ni2 N6 86.88(5) 2_656 1_545 ?
O4 Ni2 N6 86.88(5) . 1_545 ?
O3 Ni2 N5 88.49(5) . . ?
O3 Ni2 N5 88.49(5) 2_656 . ?
O4 Ni2 N5 93.12(5) 2_656 . ?
O4 Ni2 N5 93.12(5) . . ?
N6 Ni2 N5 180.000(1) 1_545 . ?
C4 N1 C3 125.8(2) . . ?
C5 N2 C4 116.8(2) . . ?
C6 N3 C6 117.3(3) 2_556 . ?
C6 N3 Ni1 121.36(16) 2_556 . ?
C6 N3 Ni1 121.36(16) . . ?
C11 N4 C11 115.0(3) 2_556 . ?
C11 N4 Ni1 122.50(17) 2_556 1_565 ?
C11 N4 Ni1 122.50(17) . 1_565 ?
C12 N5 C12 117.3(3) . 2_656 ?
C12 N5 Ni2 121.34(16) . . ?
C12 N5 Ni2 121.34(16) 2_656 . ?
C17 N6 C17 115.3(3) 2_656 . ?
C17 N6 Ni2 122.36(16) 2_656 1_565 ?
C17 N6 Ni2 122.36(16) . 1_565 ?
C3 O1 Ni1 118.63(15) . . ?
C1 O2 Ni1 128.55(15) . . ?
C1 O3 Ni2 129.25(15) . . ?
O3 C1 O2 121.8(2) . . ?
O3 C1 C2 118.5(2) . . ?
O2 C1 C2 119.6(2) . . ?
C5 C2 C3 115.9(2) . . ?
C5 C2 C1 119.4(2) . . ?
C3 C2 C1 124.5(2) . . ?
O1 C3 N1 116.9(2) . . ?
O1 C3 C2 128.4(2) . . ?
N1 C3 C2 114.7(2) . . ?
O5 C4 N2 122.9(2) . . ?
O5 C4 N1 118.4(2) . . ?
N2 C4 N1 118.7(2) . . ?
N2 C5 C2 127.8(2) . . ?
N2 C5 H5 116.1 . . ?
C2 C5 H5 116.1 . . ?
N3 C6 C7 123.2(3) . . ?
N3 C6 H6 118.4 . . ?
C7 C6 H6 118.4 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C7 115.6(4) . 2_556 ?
C7 C8 C9 122.18(18) . . ?
C7 C8 C9 122.18(18) 2_556 . ?
C10 C9 C10 116.2(4) . 2_556 ?
C10 C9 C8 121.89(19) . . ?
C10 C9 C8 121.89(19) 2_556 . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
N4 C11 C10 124.4(3) . . ?
N4 C11 H11 117.8 . . ?
C10 C11 H11 117.8 . . ?
N5 C12 C13 122.7(3) . . ?
N5 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C13 116.8(3) 2_656 . ?
C13 C14 C15 121.60(17) 2_656 . ?
C13 C14 C15 121.60(17) . . ?
C16 C15 C16 115.4(3) . 2_656 ?
C16 C15 C14 122.31(17) . . ?
C16 C15 C14 122.31(17) 2_656 . ?
C15 C16 C17 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
N6 C17 C16 124.1(3) . . ?
N6 C17 H17 118.0 . . ?
C16 C17 H17 118.0 . . ?
C19 C18 C22 120.0(5) . . ?
C19 C18 C18 121.3(9) . 3_576 ?
C22 C18 C18 118.3(9) . 3_576 ?
C18 C19 C20 120.3(7) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
N7 C20 C19 117.8(7) . . ?
N7 C20 H20 121.1 . . ?
C19 C20 H20 121.1 . . ?
C20 N7 C21 123.0(8) . . ?
N7 C21 C22 119.0(8) . . ?
N7 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C18 C22 C21 119.8(7) . . ?
C18 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.70
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.720
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.063
