# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_KS7b_P-1
_database_code_depnum_ccdc_archive 'CCDC 1402774'
_audit_update_record             
;
2015-06-18 deposited with the CCDC.
2015-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 Cu N10 O6'
_chemical_formula_weight         579.99
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           Triclinic
_space_group_IT_number           2
_symmetry_space_group_name_H-M   P-1
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7150(12)
_cell_length_b                   8.2580(13)
_cell_length_c                   9.5940(16)
_cell_angle_alpha                115.020(5)
_cell_angle_beta                 92.541(5)
_cell_angle_gamma                90.020(5)
_cell_volume                     553.21(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1622
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      25.26

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_F_000             295
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    1.055
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_T_max  0.990
_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                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            6554
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.346
_diffrn_reflns_theta_max         29.716
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2681
_reflns_number_gt                2064
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0383P)²+0.1495P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2681
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.0965
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3104(3) 0.3729(3) 0.2031(3) 0.0159(6) Uani 1 1 d . . . . .
H1 H 0.2845 0.2674 0.2114 0.019 Uiso 1 1 calc R U . . .
C2 C 0.4112(3) 0.6367(3) 0.2513(3) 0.0134(5) Uani 1 1 d . . . . .
C3 C 0.4926(3) 0.8053(3) 0.3170(3) 0.0167(6) Uani 1 1 d . . . . .
H3A H 0.5530 0.8469 0.4121 0.020 Uiso 1 1 calc R U . . .
C4 C 0.4796(3) 0.9070(3) 0.2348(3) 0.0185(6) Uani 1 1 d . . . . .
H4 H 0.5328 1.0196 0.2749 0.022 Uiso 1 1 calc R U . . .
C5 C 0.3881(3) 0.8443(3) 0.0920(3) 0.0181(6) Uani 1 1 d . . . . .
H5 H 0.3817 0.9174 0.0402 0.022 Uiso 1 1 calc R U . . .
C6 C 0.3072(3) 0.6788(3) 0.0254(3) 0.0153(6) Uani 1 1 d . . . . .
H6 H 0.2471 0.6381 -0.0697 0.018 Uiso 1 1 calc R U . . .
C7 C 0.3205(3) 0.5751(3) 0.1087(3) 0.0133(5) Uani 1 1 d . . . . .
C8 C 0.1629(3) 0.2779(3) -0.0507(3) 0.0143(5) Uani 1 1 d . . . . .
C9 C 0.0624(3) -0.0028(3) -0.1785(3) 0.0195(6) Uani 1 1 d . . . . .
H9 H 0.0485 -0.1191 -0.1882 0.023 Uiso 1 1 calc R U . . .
C10 C -0.0058(3) 0.0395(4) -0.2940(3) 0.0194(6) Uani 1 1 d . . . . .
H10 H -0.0658 -0.0452 -0.3803 0.023 Uiso 1 1 calc R U . . .
C11 C 0.0185(3) 0.2121(4) -0.2763(3) 0.0182(6) Uani 1 1 d . . . . .
H11 H -0.0256 0.2438 -0.3528 0.022 Uiso 1 1 calc R U . . .
Cu1 Cu 0.5000 0.5000 0.5000 0.01388(15) Uani 1 2 d S . P . .
N1 N 0.4017(3) 0.5054(3) 0.3084(2) 0.0138(5) Uani 1 1 d . . . . .
N2 N 0.2576(3) 0.4052(3) 0.0813(2) 0.0139(5) Uani 1 1 d . . . . .
N3 N 0.1475(3) 0.1173(3) -0.0532(3) 0.0169(5) Uani 1 1 d . . . . .
N4 N 0.1043(3) 0.3371(3) -0.1516(2) 0.0159(5) Uani 1 1 d . . . . .
N5 N 0.1907(3) 0.5181(3) 0.5997(3) 0.0170(5) Uani 1 1 d . . . . .
O1 O 0.2998(2) 0.6439(2) 0.6167(2) 0.0185(4) Uani 1 1 d . . . . .
O2 O 0.2351(2) 0.3600(2) 0.5189(2) 0.0193(4) Uani 1 1 d . . . . .
O3 O 0.0518(2) 0.5557(2) 0.6619(2) 0.0200(4) Uani 1 1 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 N1 1.310(3) . ?
C1 N2 1.351(3) . ?
C2 C7 1.395(4) . ?
C2 C3 1.397(3) . ?
C2 N1 1.409(3) . ?
C3 C4 1.375(4) . ?
C4 C5 1.399(4) . ?
C5 C6 1.375(3) . ?
C6 C7 1.398(3) . ?
C7 N2 1.396(3) . ?
C8 N4 1.320(3) . ?
C8 N3 1.322(3) . ?
C8 N2 1.426(3) . ?
C9 N3 1.335(3) . ?
C9 C10 1.380(4) . ?
C10 C11 1.374(4) . ?
C11 N4 1.349(3) . ?
Cu1 N1 1.976(2) . ?
Cu1 N1 1.976(2) 2_666 ?
Cu1 O1 2.0200(18) 2_666 ?
Cu1 O1 2.0200(18) . ?
Cu1 O2 2.3991(18) 2_666 ?
Cu1 O2 2.3991(18) . ?
N5 O3 1.225(3) . ?
N5 O2 1.261(3) . ?
N5 O1 1.287(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 113.0(2) . . ?
C7 C2 C3 121.2(2) . . ?
C7 C2 N1 109.1(2) . . ?
C3 C2 N1 129.7(2) . . ?
C4 C3 C2 117.1(2) . . ?
C3 C4 C5 121.3(2) . . ?
C6 C5 C4 122.5(2) . . ?
C5 C6 C7 116.3(2) . . ?
C2 C7 N2 105.1(2) . . ?
C2 C7 C6 121.6(2) . . ?
N2 C7 C6 133.3(2) . . ?
N4 C8 N3 129.8(2) . . ?
N4 C8 N2 115.7(2) . . ?
N3 C8 N2 114.5(2) . . ?
N3 C9 C10 122.3(2) . . ?
C11 C10 C9 117.2(2) . . ?
N4 C11 C10 122.3(3) . . ?
N1 Cu1 N1 180 . 2_666 ?
N1 Cu1 O1 89.73(8) . 2_666 ?
N1 Cu1 O1 90.27(8) 2_666 2_666 ?
N1 Cu1 O1 90.27(8) . . ?
N1 Cu1 O1 89.73(8) 2_666 . ?
O1 Cu1 O1 180 2_666 . ?
N1 Cu1 O2 91.24(7) . 2_666 ?
N1 Cu1 O2 88.76(7) 2_666 2_666 ?
O1 Cu1 O2 58.15(6) 2_666 2_666 ?
O1 Cu1 O2 121.85(7) . 2_666 ?
N1 Cu1 O2 88.76(7) . . ?
N1 Cu1 O2 91.24(7) 2_666 . ?
O1 Cu1 O2 121.85(7) 2_666 . ?
O1 Cu1 O2 58.15(6) . . ?
O2 Cu1 O2 180 2_666 . ?
C1 N1 C2 105.4(2) . . ?
C1 N1 Cu1 123.23(18) . . ?
C2 N1 Cu1 131.38(17) . . ?
C1 N2 C7 107.4(2) . . ?
C1 N2 C8 123.4(2) . . ?
C7 N2 C8 129.2(2) . . ?
C8 N3 C9 114.4(2) . . ?
C8 N4 C11 114.0(2) . . ?
O3 N5 O2 123.4(2) . . ?
O3 N5 O1 119.7(2) . . ?
O2 N5 O1 117.0(2) . . ?
N5 O1 Cu1 100.83(14) . . ?
N5 O2 Cu1 84.00(13) . . ?

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
C7 C2 C3 C4 -0.2(4) . . . . ?
N1 C2 C3 C4 -179.5(2) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C3 C2 C7 N2 -179.8(2) . . . . ?
N1 C2 C7 N2 -0.3(3) . . . . ?
C3 C2 C7 C6 0.1(4) . . . . ?
N1 C2 C7 C6 179.6(2) . . . . ?
C5 C6 C7 C2 -0.1(4) . . . . ?
C5 C6 C7 N2 179.7(3) . . . . ?
N3 C9 C10 C11 0.6(4) . . . . ?
C9 C10 C11 N4 -0.3(4) . . . . ?
N2 C1 N1 C2 -0.3(3) . . . . ?
N2 C1 N1 Cu1 -179.46(16) . . . . ?
C7 C2 N1 C1 0.4(3) . . . . ?
C3 C2 N1 C1 179.8(3) . . . . ?
C7 C2 N1 Cu1 179.42(17) . . . . ?
C3 C2 N1 Cu1 -1.2(4) . . . . ?
N1 C1 N2 C7 0.2(3) . . . . ?
N1 C1 N2 C8 177.2(2) . . . . ?
C2 C7 N2 C1 0.1(3) . . . . ?
C6 C7 N2 C1 -179.8(3) . . . . ?
C2 C7 N2 C8 -176.7(2) . . . . ?
C6 C7 N2 C8 3.4(4) . . . . ?
N4 C8 N2 C1 172.7(2) . . . . ?
N3 C8 N2 C1 -7.4(3) . . . . ?
N4 C8 N2 C7 -11.0(4) . . . . ?
N3 C8 N2 C7 168.9(2) . . . . ?
N4 C8 N3 C9 1.4(4) . . . . ?
N2 C8 N3 C9 -178.5(2) . . . . ?
C10 C9 N3 C8 -1.0(4) . . . . ?
N3 C8 N4 C11 -1.1(4) . . . . ?
N2 C8 N4 C11 178.7(2) . . . . ?
C10 C11 N4 C8 0.5(4) . . . . ?
O3 N5 O1 Cu1 177.23(18) . . . . ?
O2 N5 O1 Cu1 -2.3(2) . . . . ?
O3 N5 O2 Cu1 -177.6(2) . . . . ?
O1 N5 O2 Cu1 1.94(19) . . . . ?

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.093
_shelxl_version_number           2014-3
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1402775'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-06-30 downloaded from the CCDC.
;

_audit_creation_date             2014-09-08T13:06:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C11 H8 Cu0.50 N5 O3'
_chemical_formula_weight         289.99

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.354(4)
_cell_length_b                   9.780(2)
_cell_length_c                   16.2709(14)
_cell_angle_alpha                90
_cell_angle_beta                 104.57(4)
_cell_angle_gamma                90
_cell_volume                     2364.7(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       flat
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1180
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
'x-axis points to radiation source - matrix specified in reciprocal space'
_diffrn_orient_matrix_ub_11      -0.064954
_diffrn_orient_matrix_ub_12      0.02495
_diffrn_orient_matrix_ub_13      -0.021472
_diffrn_orient_matrix_ub_21      -0.016419
_diffrn_orient_matrix_ub_22      -0.099284
_diffrn_orient_matrix_ub_23      -0.004492
_diffrn_orient_matrix_ub_31      -0.006668
_diffrn_orient_matrix_ub_32      0.001478
_diffrn_orient_matrix_ub_33      0.059612
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_standards_number         8
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 -4 -3
-2 -4 -3
-2 -4 -3
-2 -4 -3
-2 -4 -3

_diffrn_reflns_number            0
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       -1000000
_diffrn_reflns_theta_min         2.493
_diffrn_reflns_theta_max         24.958
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.97
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 0.97
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 0.97
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             2070
_reflns_number_gt                1458
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+1.5757P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2070
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.098
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.24
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1 0.21352(7) 0.25 0.0549(2) Uani 1 d . .
N1 N 0.96515(18) 0.0787(3) 0.15671(15) 0.0520(7) Uani 1 d . .
N2 N 0.8835(2) 0.3664(3) 0.29873(18) 0.0571(8) Uani 1 d . .
N3 N 0.87694(16) -0.0300(3) 0.04712(14) 0.0450(6) Uani 1 d . .
N6 N 0.73033(18) 0.0283(3) -0.01891(16) 0.0573(8) Uani 1 d . .
N8 N 0.80011(18) -0.1618(3) -0.06788(16) 0.0561(7) Uani 1 d . .
O1 O 0.85120(16) 0.2832(3) 0.24069(15) 0.0680(7) Uani 1 d . .
O2 O 0.96975(17) 0.3618(3) 0.32606(15) 0.0700(7) Uani 1 d . .
O3 O 0.8386(2) 0.4455(3) 0.32812(19) 0.0858(9) Uani 1 d . .
C2 C 0.8858(2) 0.0765(4) 0.10131(19) 0.0544(9) Uani 1 d . .
H2 H 0.841 0.1411 0.0998 0.065 Uiso 1 calc . .
C4 C 0.9576(2) -0.1034(3) 0.06739(18) 0.0440(8) Uani 1 d . .
C5 C 1.0122(2) -0.0334(3) 0.13665(17) 0.0453(8) Uani 1 d . .
C7 C 0.7968(2) -0.0570(3) -0.01838(17) 0.0436(8) Uani 1 d . .
C9 C 0.7239(2) -0.1831(4) -0.1288(2) 0.0631(10) Uani 1 d . .
H9 H 0.7218 -0.2552 -0.1666 0.076 Uiso 1 calc . .
C10 C 0.6503(2) -0.1032(4) -0.1371(2) 0.0633(10) Uani 1 d . .
H10 H 0.5981 -0.119 -0.1796 0.076 Uiso 1 calc . .
C11 C 0.6555(2) 0.0018(4) -0.0805(2) 0.0667(11) Uani 1 d . .
H11 H 0.6053 0.0571 -0.0848 0.08 Uiso 1 calc . .
C12 C 0.9878(2) -0.2207(4) 0.03495(19) 0.0542(9) Uani 1 d . .
H12 H 0.9521 -0.2675 -0.0111 0.065 Uiso 1 calc . .
C13 C 1.0733(2) -0.2640(4) 0.0747(2) 0.0645(10) Uani 1 d . .
H13 H 1.0952 -0.343 0.0553 0.077 Uiso 1 calc . .
C14 C 1.1283(2) -0.1941(4) 0.1429(2) 0.0668(11) Uani 1 d . .
H14 H 1.1858 -0.2271 0.1672 0.08 Uiso 1 calc . .
C15 C 1.0995(2) -0.0776(4) 0.17501(19) 0.0577(10) Uani 1 d . .
H15 H 1.1363 -0.0303 0.2202 0.069 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.980(3) 2_755 ?
Cu1 N1 1.980(3) . ?
Cu1 O2 2.034(3) 2_755 ?
Cu1 O2 2.034(3) . ?
Cu1 O1 2.352(3) 2_755 ?
Cu1 O1 2.352(3) . ?
N1 C2 1.321(4) . ?
N1 C5 1.395(4) . ?
N2 O3 1.212(4) . ?
N2 O1 1.251(3) . ?
N2 O2 1.287(4) . ?
N3 C2 1.349(4) . ?
N3 C4 1.397(4) . ?
N3 C7 1.436(4) . ?
N6 C7 1.315(4) . ?
N6 C11 1.346(4) . ?
N8 C7 1.313(4) . ?
N8 C9 1.347(4) . ?
C4 C12 1.390(4) . ?
C4 C5 1.403(4) . ?
C5 C15 1.397(4) . ?
C9 C10 1.353(5) . ?
C10 C11 1.367(5) . ?
C12 C13 1.376(5) . ?
C13 C14 1.393(5) . ?
C14 C15 1.373(5) . ?

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 Cu1 N1 96.49(15) 2_755 . ?
N1 Cu1 O2 151.88(10) 2_755 2_755 ?
N1 Cu1 O2 93.86(11) . 2_755 ?
N1 Cu1 O2 93.86(11) 2_755 . ?
N1 Cu1 O2 151.88(10) . . ?
O2 Cu1 O2 89.08(15) 2_755 . ?
N1 Cu1 O1 94.17(10) 2_755 2_755 ?
N1 Cu1 O1 108.24(11) . 2_755 ?
O2 Cu1 O1 57.73(10) 2_755 2_755 ?
O2 Cu1 O1 96.95(10) . 2_755 ?
N1 Cu1 O1 108.24(11) 2_755 . ?
N1 Cu1 O1 94.17(10) . . ?
O2 Cu1 O1 96.95(10) 2_755 . ?
O2 Cu1 O1 57.73(10) . . ?
O1 Cu1 O1 146.32(13) 2_755 . ?
C2 N1 C5 105.7(3) . . ?
C2 N1 Cu1 124.0(2) . . ?
C5 N1 Cu1 130.3(2) . . ?
O3 N2 O1 123.8(3) . . ?
O3 N2 O2 121.6(3) . . ?
O1 N2 O2 114.6(3) . . ?
C2 N3 C4 107.7(3) . . ?
C2 N3 C7 123.6(3) . . ?
C4 N3 C7 128.6(3) . . ?
C7 N6 C11 113.5(3) . . ?
C7 N8 C9 114.3(3) . . ?
N2 O1 Cu1 86.9(2) . . ?
N2 O2 Cu1 100.8(2) . . ?
N1 C2 N3 112.5(3) . . ?
C12 C4 N3 134.0(3) . . ?
C12 C4 C5 121.3(3) . . ?
N3 C4 C5 104.7(3) . . ?
N1 C5 C15 129.3(3) . . ?
N1 C5 C4 109.4(3) . . ?
C15 C5 C4 121.3(3) . . ?
N8 C7 N6 129.9(3) . . ?
N8 C7 N3 116.1(3) . . ?
N6 C7 N3 114.0(3) . . ?
N8 C9 C10 122.2(3) . . ?
C9 C10 C11 117.4(3) . . ?
N6 C11 C10 122.7(3) . . ?
C13 C12 C4 116.4(3) . . ?
C12 C13 C14 122.7(4) . . ?
C15 C14 C13 121.4(3) . . ?
C14 C15 C5 116.9(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O1 0.93 2.65 3.181(4) 116.8 .
C9 H9 O3 0.93 2.6 3.287(5) 130.9 6
C11 H11 O2 0.93 2.36 3.169(4) 146 8_455
C12 H12 N8 0.93 2.51 3.001(4) 113.5 .


# END of CIF
####################################################################### 
# 
# 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_pm181
_database_code_depnum_ccdc_archive 'CCDC 1402776'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-06-30 downloaded from the CCDC.
;

_audit_creation_date             2012-06-13T16:24:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H26 Co1 N10 O6'
_chemical_formula_sum            'C22 H16 Co N10 O6'
_chemical_formula_weight         575.38
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.101(6)
_cell_length_b                   9.635(3)
_cell_length_c                   16.508(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.54(6)
_cell_angle_gamma                90
_cell_volume                     2335.1(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1172
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.7107
_exptl_absorpt_correction_T_max  0.8255

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      -0.032277
_diffrn_orient_matrix_ub_12      0.091067
_diffrn_orient_matrix_ub_13      -0.010289
_diffrn_orient_matrix_ub_21      -0.059139
_diffrn_orient_matrix_ub_22      -0.047497
_diffrn_orient_matrix_ub_23      -0.000783
_diffrn_orient_matrix_ub_31      0.010008
_diffrn_orient_matrix_ub_32      0.014986
_diffrn_orient_matrix_ub_33      0.061449
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_standards_number         1
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-6 2 -4

_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_number            2539
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         26.96
_diffrn_reflns_theta_full        26.96
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             2539
_reflns_number_gt                1602
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0467P)²+0.1464P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2539
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.089
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5 0.22089(6) 0.25 0.0463(2) Uani 1 2 d S . .
O1 O 0.36495(14) 0.2798(2) 0.24206(13) 0.0588(6) Uani 1 1 d . . .
O2 O 0.46351(15) 0.3929(3) 0.32995(17) 0.0800(8) Uani 1 1 d . . .
O3 O 0.32081(16) 0.4476(3) 0.31161(16) 0.0705(7) Uani 1 1 d . . .
N1 N 0.46403(15) 0.0845(3) 0.15333(14) 0.0456(6) Uani 1 1 d . . .
N2 N 0.38081(17) 0.3773(3) 0.29577(16) 0.0530(7) Uani 1 1 d . . .
N3 N 0.37745(14) -0.0286(2) 0.04566(13) 0.0406(6) Uani 1 1 d . . .
N6 N 0.23002(16) 0.0320(3) -0.01912(15) 0.0523(7) Uani 1 1 d . . .
N8 N 0.30207(16) -0.1611(3) -0.06683(15) 0.0499(6) Uani 1 1 d . . .
C2 C 0.38557(19) 0.0809(3) 0.09877(17) 0.0455(7) Uani 1 1 d . . .
H2 H 0.34 0.1467 0.0966 0.055 Uiso 1 1 calc R . .
C4 C 0.45918(17) -0.1035(3) 0.06762(16) 0.0380(6) Uani 1 1 d . . .
C5 C 0.51211(18) -0.0315(3) 0.13506(16) 0.0409(7) Uani 1 1 d . . .
C7 C 0.29823(18) -0.0555(3) -0.01796(16) 0.0400(7) Uani 1 1 d . . .
C9 C 0.2252(2) -0.1820(4) -0.12600(19) 0.0547(8) Uani 1 1 d . . .
H9 H 0.2234 -0.2558 -0.1627 0.066 Uiso 1 1 calc R . .
C10 C 0.1498(2) -0.1003(4) -0.13474(18) 0.0543(8) Uani 1 1 d . . .
H10 H 0.0975 -0.116 -0.1763 0.065 Uiso 1 1 calc R . .
C11 C 0.1557(2) 0.0062(4) -0.0787(2) 0.0594(9) Uani 1 1 d . . .
H11 H 0.1053 0.0634 -0.0825 0.071 Uiso 1 1 calc R . .
C12 C 0.49049(19) -0.2233(3) 0.03712(17) 0.0470(7) Uani 1 1 d . . .
H12 H 0.4556 -0.2708 -0.0084 0.056 Uiso 1 1 calc R . .
C13 C 0.5759(2) -0.2684(4) 0.0777(2) 0.0566(8) Uani 1 1 d . . .
H13 H 0.5987 -0.3493 0.0594 0.068 Uiso 1 1 calc R . .
C14 C 0.6296(2) -0.1968(4) 0.14527(19) 0.0578(9) Uani 1 1 d . . .
H14 H 0.6869 -0.231 0.1708 0.069 Uiso 1 1 calc R . .
C15 C 0.59920(19) -0.0769(4) 0.17477(18) 0.0511(8) Uani 1 1 d . . .
H15 H 0.635 -0.0282 0.2192 0.061 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N1 2.040(2) . ?
Co1 N1 2.040(2) 2_655 ?
Co1 O1 2.091(2) 2_655 ?
Co1 O1 2.091(2) . ?
Co1 O2 2.266(3) . ?
Co1 O2 2.266(3) 2_655 ?
O1 N2 1.275(3) . ?
O2 N2 1.253(3) . ?
O3 N2 1.208(3) . ?
N1 C2 1.310(3) . ?
N1 C5 1.403(4) . ?
N3 C2 1.359(3) . ?
N3 C4 1.402(3) . ?
N3 C7 1.419(3) . ?
N6 C7 1.328(4) . ?
N6 C11 1.330(4) . ?
N8 C7 1.309(3) . ?
N8 C9 1.346(4) . ?
C2 H2 0.93 . ?
C4 C12 1.386(4) . ?
C4 C5 1.394(4) . ?
C5 C15 1.395(4) . ?
C9 C10 1.364(4) . ?
C9 H9 0.93 . ?
C10 C11 1.371(4) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.377(4) . ?
C12 H12 0.93 . ?
C13 C14 1.398(5) . ?
C13 H13 0.93 . ?
C14 C15 1.373(4) . ?
C14 H14 0.93 . ?
C15 H15 0.93 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Co1 N1 99.80(14) . 2_655 ?
N1 Co1 O1 107.52(10) . 2_655 ?
N1 Co1 O1 92.80(10) 2_655 2_655 ?
N1 Co1 O1 92.80(10) . . ?
N1 Co1 O1 107.52(10) 2_655 . ?
O1 Co1 O1 148.49(14) 2_655 . ?
N1 Co1 O2 150.50(9) . . ?
N1 Co1 O2 94.13(10) 2_655 . ?
O1 Co1 O2 97.55(10) 2_655 . ?
O1 Co1 O2 58.08(9) . . ?
N1 Co1 O2 94.13(10) . 2_655 ?
N1 Co1 O2 150.50(9) 2_655 2_655 ?
O1 Co1 O2 58.08(9) 2_655 2_655 ?
O1 Co1 O2 97.55(10) . 2_655 ?
O2 Co1 O2 85.97(15) . 2_655 ?
N2 O1 Co1 97.74(17) . . ?
N2 O2 Co1 90.14(19) . . ?
C2 N1 C5 105.2(2) . . ?
C2 N1 Co1 125.9(2) . . ?
C5 N1 Co1 128.65(18) . . ?
O3 N2 O2 123.7(3) . . ?
O3 N2 O1 122.3(3) . . ?
O2 N2 O1 114.0(3) . . ?
C2 N3 C4 107.0(2) . . ?
C2 N3 C7 123.5(2) . . ?
C4 N3 C7 129.5(2) . . ?
C7 N6 C11 114.2(3) . . ?
C7 N8 C9 114.1(3) . . ?
N1 C2 N3 113.2(3) . . ?
N1 C2 H2 123.4 . . ?
N3 C2 H2 123.4 . . ?
C12 C4 C5 121.6(2) . . ?
C12 C4 N3 133.6(3) . . ?
C5 C4 N3 104.8(2) . . ?
C4 C5 C15 121.3(3) . . ?
C4 C5 N1 109.8(2) . . ?
C15 C5 N1 128.8(3) . . ?
N8 C7 N6 129.1(3) . . ?
N8 C7 N3 116.5(2) . . ?
N6 C7 N3 114.3(2) . . ?
N8 C9 C10 123.2(3) . . ?
N8 C9 H9 118.4 . . ?
C10 C9 H9 118.4 . . ?
C9 C10 C11 116.1(3) . . ?
C9 C10 H10 121.9 . . ?
C11 C10 H10 121.9 . . ?
N6 C11 C10 123.3(3) . . ?
N6 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C13 C12 C4 116.5(3) . . ?
C13 C12 H12 121.7 . . ?
C4 C12 H12 121.7 . . ?
C12 C13 C14 122.2(3) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C15 C14 C13 121.3(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C5 117.0(3) . . ?
C14 C15 H15 121.5 . . ?
C5 C15 H15 121.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Co1 O1 N2 -173.81(18) . . . . ?
N1 Co1 O1 N2 85.00(19) 2_655 . . . ?
O1 Co1 O1 N2 -42.79(16) 2_655 . . . ?
O2 Co1 O1 N2 1.18(17) . . . . ?
O2 Co1 O1 N2 -79.26(19) 2_655 . . . ?
N1 Co1 O2 N2 9.0(3) . . . . ?
N1 Co1 O2 N2 -109.3(2) 2_655 . . . ?
O1 Co1 O2 N2 157.34(18) 2_655 . . . ?
O1 Co1 O2 N2 -1.19(17) . . . . ?
O2 Co1 O2 N2 100.3(2) 2_655 . . . ?
N1 Co1 N1 C2 124.6(3) 2_655 . . . ?
O1 Co1 N1 C2 -139.3(2) 2_655 . . . ?
O1 Co1 N1 C2 16.3(3) . . . . ?
O2 Co1 N1 C2 7.6(4) . . . . ?
O2 Co1 N1 C2 -81.5(3) 2_655 . . . ?
N1 Co1 N1 C5 -48.7(2) 2_655 . . . ?
O1 Co1 N1 C5 47.4(2) 2_655 . . . ?
O1 Co1 N1 C5 -157.1(2) . . . . ?
O2 Co1 N1 C5 -165.7(2) . . . . ?
O2 Co1 N1 C5 105.2(2) 2_655 . . . ?
Co1 O2 N2 O3 -178.1(3) . . . . ?
Co1 O2 N2 O1 1.8(3) . . . . ?
Co1 O1 N2 O3 178.0(3) . . . . ?
Co1 O1 N2 O2 -2.0(3) . . . . ?
C5 N1 C2 N3 0.2(3) . . . . ?
Co1 N1 C2 N3 -174.45(18) . . . . ?
C4 N3 C2 N1 -0.4(3) . . . . ?
C7 N3 C2 N1 179.1(2) . . . . ?
C2 N3 C4 C12 179.5(3) . . . . ?
C7 N3 C4 C12 0.1(5) . . . . ?
C2 N3 C4 C5 0.4(3) . . . . ?
C7 N3 C4 C5 -179.0(3) . . . . ?
C12 C4 C5 C15 0.1(4) . . . . ?
N3 C4 C5 C15 179.3(3) . . . . ?
C12 C4 C5 N1 -179.5(2) . . . . ?
N3 C4 C5 N1 -0.3(3) . . . . ?
C2 N1 C5 C4 0.1(3) . . . . ?
Co1 N1 C5 C4 174.52(19) . . . . ?
C2 N1 C5 C15 -179.5(3) . . . . ?
Co1 N1 C5 C15 -5.1(4) . . . . ?
C9 N8 C7 N6 -0.1(5) . . . . ?
C9 N8 C7 N3 180.0(3) . . . . ?
C11 N6 C7 N8 0.3(5) . . . . ?
C11 N6 C7 N3 -179.8(3) . . . . ?
C2 N3 C7 N8 176.8(3) . . . . ?
C4 N3 C7 N8 -3.9(4) . . . . ?
C2 N3 C7 N6 -3.1(4) . . . . ?
C4 N3 C7 N6 176.2(3) . . . . ?
C7 N8 C9 C10 0.2(5) . . . . ?
N8 C9 C10 C11 -0.5(5) . . . . ?
C7 N6 C11 C10 -0.6(5) . . . . ?
C9 C10 C11 N6 0.7(5) . . . . ?
C5 C4 C12 C13 0.9(4) . . . . ?
N3 C4 C12 C13 -178.0(3) . . . . ?
C4 C12 C13 C14 -1.0(5) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C5 1.0(5) . . . . ?
C4 C5 C15 C14 -1.1(4) . . . . ?
N1 C5 C15 C14 178.5(3) . . . . ?

# END of CIF
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1402777'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-06-30 downloaded from the CCDC.
;

_audit_creation_date             2014-09-19T12:53:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22  H16  N10  O6  Ni1'
_chemical_formula_sum            'C22 H16 N10 Ni O6'
_chemical_formula_weight         575.16

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.327(8)
_cell_length_b                   9.623(6)
_cell_length_c                   16.459(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.47(4)
_cell_angle_gamma                90
_cell_volume                     2351(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       flat
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
'x-axis points to radiation source - matrix specified in reciprocal space'
_diffrn_orient_matrix_ub_11      0.023265
_diffrn_orient_matrix_ub_12      0.079348
_diffrn_orient_matrix_ub_13      0.038599
_diffrn_orient_matrix_ub_21      -0.061618
_diffrn_orient_matrix_ub_22      0.014631
_diffrn_orient_matrix_ub_23      0.008685
_diffrn_orient_matrix_ub_31      0.014353
_diffrn_orient_matrix_ub_32      -0.065463
_diffrn_orient_matrix_ub_33      0.048766
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_standards_number         2
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 -2 4
-2 -2 4
0 0 0
0 0 0
0 0 0

_diffrn_reflns_number            3019
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.523
_diffrn_reflns_theta_max         24.976
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.97
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 0.97
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 0.97
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             2064
_reflns_number_gt                502
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2064
_refine_ls_number_parameters     177
_refine_ls_number_restraints     6
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.2903
_refine_ls_R_factor_gt           0.0925
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   0.841
_refine_ls_restrained_S_all      0.84
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.089

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 1 0.2278(3) 0.25 0.0561(8) Uani 1 d . .
O1 O 1.1340(5) 0.2727(10) 0.2577(5) 0.072(3) Uani 1 d . .
O2 O 1.0323(6) 0.3933(9) 0.1711(5) 0.073(3) Uani 1 d . .
O3 O 1.1713(7) 0.4447(12) 0.1849(7) 0.097(4) Uani 1 d . .
N1 N 0.9685(7) 0.0889(11) 0.1546(6) 0.056(3) Uani 1 d . .
N2 N 1.1170(8) 0.3705(14) 0.2036(9) 0.077(4) Uani 1 d . .
N3 N 0.8792(6) -0.0298(12) 0.0489(7) 0.053(3) Uani 1 d . .
N6 N 0.7356(8) 0.0324(11) -0.0156(7) 0.066(4) Uani 1 d . .
N8 N 0.8048(7) -0.1630(11) -0.0645(7) 0.065(3) Uani 1 d . .
C2 C 0.8874(8) 0.0837(15) 0.1023(8) 0.075(5) Uani 1 d . .
H2 H 0.8419 0.1479 0.1014 0.09 Uiso 1 calc . .
C4 C 0.9606(8) -0.1022(14) 0.0685(8) 0.052(4) Uani 1 d . .
C5 C 1.0153(9) -0.0258(16) 0.1383(8) 0.064(4) Uani 1 d . .
C7 C 0.8026(9) -0.0550(14) -0.0153(8) 0.059(4) Uani 1 d . .
C9 C 0.7285(9) -0.1830(14) -0.1258(8) 0.073(5) Uani 1 d . .
H9 H 0.7269 -0.2552 -0.1637 0.088 Uiso 1 calc . .
C10 C 0.6526(9) -0.1003(14) -0.1346(8) 0.070(5) Uani 1 d . .
H10 H 0.6011 -0.1133 -0.1779 0.084 Uiso 1 calc . .
C11 C 0.6582(9) 0.0000(16) -0.0764(8) 0.076(5) Uani 1 d . .
H11 H 0.6065 0.0511 -0.0773 0.092 Uiso 1 calc . .
C12 C 0.9936(7) -0.2213(15) 0.0400(7) 0.065(4) Uani 1 d . .
H12 H 0.9587 -0.2709 -0.005 0.077 Uiso 1 calc . .
C13 C 1.0812(8) -0.2662(16) 0.0805(8) 0.080(5) Uani 1 d . .
H13 H 1.1045 -0.3461 0.0621 0.096 Uiso 1 calc . .
C14 C 1.1328(9) -0.1916(15) 0.1479(9) 0.082(5) Uani 1 d . .
H14 H 1.1899 -0.2239 0.1748 0.098 Uiso 1 calc . .
C15 C 1.1016(9) -0.0718(15) 0.1755(9) 0.072(5) Uani 1 d . .
H15 H 1.1384 -0.0214 0.219 0.087 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 2.026(10) 2_755 ?
Ni1 N1 2.026(10) . ?
Ni1 O1 2.071(8) . ?
Ni1 O1 2.071(8) 2_755 ?
Ni1 O2 2.188(9) . ?
Ni1 O2 2.188(9) 2_755 ?
O1 N2 1.277(14) . ?
O2 N2 1.294(12) . ?
O3 N2 1.193(13) . ?
N1 C2 1.325(13) . ?
N1 C5 1.378(15) . ?
N3 C2 1.388(14) . ?
N3 C7 1.391(14) . ?
N3 C4 1.394(13) . ?
N6 C7 1.326(14) . ?
N6 C11 1.383(15) . ?
N8 C7 1.323(13) . ?
N8 C9 1.354(13) . ?
C4 C12 1.382(15) . ?
C4 C5 1.443(16) . ?
C5 C15 1.385(16) . ?
C9 C10 1.386(15) . ?
C10 C11 1.347(15) . ?
C12 C13 1.409(13) . ?
C13 C14 1.390(15) . ?
C14 C15 1.368(16) . ?

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 Ni1 N1 97.4(6) 2_755 . ?
N1 Ni1 O1 92.9(4) 2_755 . ?
N1 Ni1 O1 103.0(4) . . ?
N1 Ni1 O1 103.0(4) 2_755 2_755 ?
N1 Ni1 O1 92.9(4) . 2_755 ?
O1 Ni1 O1 155.9(5) . 2_755 ?
N1 Ni1 O2 153.5(3) 2_755 . ?
N1 Ni1 O2 93.8(4) . . ?
O1 Ni1 O2 61.1(3) . . ?
O1 Ni1 O2 100.4(3) 2_755 . ?
N1 Ni1 O2 93.8(4) 2_755 2_755 ?
N1 Ni1 O2 153.5(3) . 2_755 ?
O1 Ni1 O2 100.4(3) . 2_755 ?
O1 Ni1 O2 61.1(3) 2_755 2_755 ?
O2 Ni1 O2 86.6(5) . 2_755 ?
N2 O1 Ni1 94.9(8) . . ?
N2 O2 Ni1 89.1(8) . . ?
C2 N1 C5 107.0(11) . . ?
C2 N1 Ni1 122.1(10) . . ?
C5 N1 Ni1 130.1(9) . . ?
O3 N2 O1 126.0(14) . . ?
O3 N2 O2 119.0(15) . . ?
O1 N2 O2 114.9(13) . . ?
C2 N3 C7 123.0(11) . . ?
C2 N3 C4 108.2(11) . . ?
C7 N3 C4 128.8(12) . . ?
C7 N6 C11 112.5(12) . . ?
C7 N8 C9 114.7(12) . . ?
N1 C2 N3 111.3(12) . . ?
C12 C4 N3 135.9(13) . . ?
C12 C4 C5 120.3(13) . . ?
N3 C4 C5 103.8(12) . . ?
N1 C5 C15 131.0(15) . . ?
N1 C5 C4 109.6(12) . . ?
C15 C5 C4 119.3(15) . . ?
N8 C7 N6 129.4(12) . . ?
N8 C7 N3 117.1(12) . . ?
N6 C7 N3 113.5(12) . . ?
N8 C9 C10 122.8(13) . . ?
C11 C10 C9 115.8(14) . . ?
C10 C11 N6 124.5(15) . . ?
C4 C12 C13 118.6(13) . . ?
C14 C13 C12 120.4(15) . . ?
C15 C14 C13 121.5(16) . . ?
C14 C15 C5 119.9(16) . . ?

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
Ni1 O1 N2 O3 174.9(15) . . . . ?
Ni1 O1 N2 O2 -0.8(12) . . . . ?
Ni1 O2 N2 O3 -175.3(13) . . . . ?
Ni1 O2 N2 O1 0.8(12) . . . . ?
C5 N1 C2 N3 -1.9(17) . . . . ?
Ni1 N1 C2 N3 -172.9(8) . . . . ?
C7 N3 C2 N1 -176.2(12) . . . . ?
C4 N3 C2 N1 0.0(17) . . . . ?
C2 N3 C4 C12 178.7(15) . . . . ?
C7 N3 C4 C12 -5(2) . . . . ?
C2 N3 C4 C5 1.8(14) . . . . ?
C7 N3 C4 C5 177.8(13) . . . . ?
C2 N1 C5 C15 -178.8(15) . . . . ?
Ni1 N1 C5 C15 -9(2) . . . . ?
C2 N1 C5 C4 3.1(15) . . . . ?
Ni1 N1 C5 C4 173.1(8) . . . . ?
C12 C4 C5 N1 179.5(12) . . . . ?
N3 C4 C5 N1 -3.0(14) . . . . ?
C12 C4 C5 C15 1(2) . . . . ?
N3 C4 C5 C15 178.6(12) . . . . ?
C9 N8 C7 N6 3(2) . . . . ?
C9 N8 C7 N3 179.9(12) . . . . ?
C11 N6 C7 N8 1(2) . . . . ?
C11 N6 C7 N3 -176.1(11) . . . . ?
C2 N3 C7 N8 176.7(13) . . . . ?
C4 N3 C7 N8 1(2) . . . . ?
C2 N3 C7 N6 -6(2) . . . . ?
C4 N3 C7 N6 178.8(13) . . . . ?
C7 N8 C9 C10 -2.4(19) . . . . ?
N8 C9 C10 C11 -2(2) . . . . ?
C9 C10 C11 N6 6(2) . . . . ?
C7 N6 C11 C10 -6(2) . . . . ?
N3 C4 C12 C13 -176.4(13) . . . . ?
C5 C4 C12 C13 0.1(19) . . . . ?
C4 C12 C13 C14 0(2) . . . . ?
C12 C13 C14 C15 -2(2) . . . . ?
C13 C14 C15 C5 3(2) . . . . ?
N1 C5 C15 C14 179.5(14) . . . . ?
C4 C5 C15 C14 -3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O1 0.93 2.56 3.018(16) 111.1 2_755
C9 H9 O3 0.93 2.48 3.224(17) 137 5_755
C11 H11 O2 0.93 2.36 3.120(15) 139.1 7_655
C12 H12 N8 0.93 2.54 3.026(15) 113 .


# END of CIF
####################################################################### 
# 
# 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_mo_KS7_05
_database_code_depnum_ccdc_archive 'CCDC 1402778'
_audit_update_record             
;
2015-06-23 deposited with the CCDC.
2015-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 Cu N10 O10'
_chemical_formula_weight         648.02
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           Triclinic
_space_group_IT_number           2
_symmetry_space_group_name_H-M   P-1
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0438(7)
_cell_length_b                   7.8981(7)
_cell_length_c                   12.0293(11)
_cell_angle_alpha                81.397(3)
_cell_angle_beta                 89.396(3)
_cell_angle_gamma                67.424(3)
_cell_volume                     610.18(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2030
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      26.90

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_F_000             331
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.978
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.733
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   
; 
 TWINABS Version 2008/0 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                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            5881
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.714
_diffrn_reflns_theta_max         29.836
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2977
_reflns_number_gt                2542
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0702P)²+0.3459P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2977
_refine_ls_number_parameters     203
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 0.5000 0.5000 0.01650(14) Uani 1 2 d S . P . .
N1 N 1.2313(3) 0.3377(3) 0.21283(17) 0.0200(4) Uani 1 1 d . . . . .
H1 H 1.3636 0.2956 0.2181 0.024 Uiso 1 1 calc R U . . .
N2 N 0.9049(3) 0.4829(3) 0.24599(16) 0.0168(4) Uani 1 1 d . . . . .
N3 N 0.5605(3) 0.6795(3) 0.22400(18) 0.0197(4) Uani 1 1 d . . . . .
N4 N 0.7473(3) 0.6312(3) 0.39713(17) 0.0161(4) Uani 1 1 d . . . . .
O1 O 1.1630(3) 0.4912(2) 0.36611(14) 0.0191(4) Uani 1 1 d . . . . .
O2 O 1.0068(3) 0.2095(3) 0.47420(15) 0.0202(4) Uani 1 1 d D . . . .
H2O1 H 0.917(4) 0.197(4) 0.435(2) 0.030 Uiso 1 1 d D U . . .
H2O2 H 1.017(5) 0.142(4) 0.5369(13) 0.030 Uiso 1 1 d D U . . .
C1 C 1.1066(4) 0.4410(3) 0.28321(19) 0.0170(5) Uani 1 1 d . . . . .
C2 C 1.1154(4) 0.3083(4) 0.1294(2) 0.0195(5) Uani 1 1 d . . . . .
C3 C 1.1793(4) 0.2101(4) 0.0402(2) 0.0241(5) Uani 1 1 d . . . . .
H3 H 1.3179 0.1520 0.0269 0.029 Uiso 1 1 calc R U . . .
C4 C 1.0258(5) 0.2032(4) -0.0281(2) 0.0251(6) Uani 1 1 d . . . . .
H4 H 1.0619 0.1390 -0.0889 0.030 Uiso 1 1 calc R U . . .
C5 C 0.8191(4) 0.2904(4) -0.0073(2) 0.0237(5) Uani 1 1 d . . . . .
H5 H 0.7200 0.2819 -0.0541 0.028 Uiso 1 1 calc R U . . .
C6 C 0.7564(4) 0.3902(4) 0.0816(2) 0.0211(5) Uani 1 1 d . . . . .
H6 H 0.6178 0.4488 0.0950 0.025 Uiso 1 1 calc R U . . .
C7 C 0.9091(4) 0.3985(3) 0.1489(2) 0.0190(5) Uani 1 1 d . . . . .
C8 C 0.7297(4) 0.6042(3) 0.2907(2) 0.0166(5) Uani 1 1 d . . . . .
C9 C 0.3963(4) 0.8005(4) 0.2653(2) 0.0218(5) Uani 1 1 d . . . . .
H9 H 0.2741 0.8553 0.2212 0.026 Uiso 1 1 calc R U . . .
C10 C 0.4007(4) 0.8477(4) 0.3712(2) 0.0205(5) Uani 1 1 d . . . . .
H10 H 0.2870 0.9369 0.3974 0.025 Uiso 1 1 calc R U . . .
C11 C 0.5804(4) 0.7568(3) 0.4355(2) 0.0182(5) Uani 1 1 d . . . . .
H11 H 0.5873 0.7826 0.5079 0.022 Uiso 1 1 calc R U . . .
N1A N 0.7480(3) 0.0728(3) 0.28189(17) 0.0179(4) Uani 1 1 d . . . . .
O1A O 0.6811(3) 0.1976(3) 0.34308(16) 0.0254(4) Uani 1 1 d . . . . .
O2A O 0.9274(3) -0.0466(3) 0.29836(16) 0.0255(4) Uani 1 1 d . . . . .
O3A O 0.6346(3) 0.0688(3) 0.20451(16) 0.0269(4) Uani 1 1 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
Cu1 O1 1.9623(17) 2_766 ?
Cu1 O1 1.9623(17) . ?
Cu1 N4 2.005(2) . ?
Cu1 N4 2.005(2) 2_766 ?
Cu1 O2 2.3437(18) 2_766 ?
Cu1 O2 2.3437(18) . ?
N1 C1 1.340(3) . ?
N1 C2 1.400(3) . ?
N2 C1 1.392(3) . ?
N2 C8 1.401(3) . ?
N2 C7 1.423(3) . ?
N3 C8 1.324(3) . ?
N3 C9 1.334(3) . ?
N4 C11 1.345(3) . ?
N4 C8 1.343(3) . ?
O1 C1 1.248(3) . ?
C2 C7 1.386(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.387(4) . ?
C4 C5 1.389(4) . ?
C5 C6 1.391(4) . ?
C6 C7 1.381(4) . ?
C9 C10 1.383(3) . ?
C10 C11 1.368(3) . ?
N1A O3A 1.245(3) . ?
N1A O2A 1.249(3) . ?
N1A O1A 1.260(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 2_766 . ?
O1 Cu1 N4 92.33(8) 2_766 . ?
O1 Cu1 N4 87.67(8) . . ?
O1 Cu1 N4 87.67(8) 2_766 2_766 ?
O1 Cu1 N4 92.33(8) . 2_766 ?
N4 Cu1 N4 180.0 . 2_766 ?
O1 Cu1 O2 86.85(7) 2_766 2_766 ?
O1 Cu1 O2 93.15(7) . 2_766 ?
N4 Cu1 O2 88.66(7) . 2_766 ?
N4 Cu1 O2 91.34(7) 2_766 2_766 ?
O1 Cu1 O2 93.15(7) 2_766 . ?
O1 Cu1 O2 86.85(7) . . ?
N4 Cu1 O2 91.34(7) . . ?
N4 Cu1 O2 88.66(7) 2_766 . ?
O2 Cu1 O2 180.0 2_766 . ?
C1 N1 C2 110.3(2) . . ?
C1 N2 C8 124.7(2) . . ?
C1 N2 C7 108.59(19) . . ?
C8 N2 C7 126.4(2) . . ?
C8 N3 C9 116.2(2) . . ?
C11 N4 C8 116.2(2) . . ?
C11 N4 Cu1 118.79(16) . . ?
C8 N4 Cu1 125.04(16) . . ?
C1 O1 Cu1 117.07(16) . . ?
O1 C1 N1 125.7(2) . . ?
O1 C1 N2 126.8(2) . . ?
N1 C1 N2 107.5(2) . . ?
C7 C2 C3 122.2(2) . . ?
C7 C2 N1 107.7(2) . . ?
C3 C2 N1 130.1(2) . . ?
C2 C3 C4 116.6(3) . . ?
C3 C4 C5 121.2(2) . . ?
C4 C5 C6 121.8(2) . . ?
C7 C6 C5 117.0(2) . . ?
C6 C7 C2 121.2(2) . . ?
C6 C7 N2 132.9(2) . . ?
C2 C7 N2 105.9(2) . . ?
N3 C8 N4 126.0(2) . . ?
N3 C8 N2 116.4(2) . . ?
N4 C8 N2 117.5(2) . . ?
N3 C9 C10 122.6(2) . . ?
C11 C10 C9 116.8(2) . . ?
N4 C11 C10 122.0(2) . . ?
O3A N1A O2A 119.8(2) . . ?
O3A N1A O1A 119.8(2) . . ?
O2A N1A O1A 120.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 N1 -143.5(2) . . . . ?
Cu1 O1 C1 N2 37.2(3) . . . . ?
C2 N1 C1 O1 -180.0(2) . . . . ?
C2 N1 C1 N2 -0.6(3) . . . . ?
C8 N2 C1 O1 6.2(4) . . . . ?
C7 N2 C1 O1 180.0(2) . . . . ?
C8 N2 C1 N1 -173.2(2) . . . . ?
C7 N2 C1 N1 0.6(3) . . . . ?
C1 N1 C2 C7 0.3(3) . . . . ?
C1 N1 C2 C3 -179.9(3) . . . . ?
C7 C2 C3 C4 -1.3(4) . . . . ?
N1 C2 C3 C4 179.0(3) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C5 C6 C7 C2 -1.1(4) . . . . ?
C5 C6 C7 N2 -178.9(3) . . . . ?
C3 C2 C7 C6 1.9(4) . . . . ?
N1 C2 C7 C6 -178.3(2) . . . . ?
C3 C2 C7 N2 -179.7(2) . . . . ?
N1 C2 C7 N2 0.1(3) . . . . ?
C1 N2 C7 C6 177.6(3) . . . . ?
C8 N2 C7 C6 -8.7(5) . . . . ?
C1 N2 C7 C2 -0.4(3) . . . . ?
C8 N2 C7 C2 173.3(2) . . . . ?
C9 N3 C8 N4 3.7(4) . . . . ?
C9 N3 C8 N2 -177.5(2) . . . . ?
C11 N4 C8 N3 -5.0(4) . . . . ?
Cu1 N4 C8 N3 175.03(19) . . . . ?
C11 N4 C8 N2 176.1(2) . . . . ?
Cu1 N4 C8 N2 -3.8(3) . . . . ?
C1 N2 C8 N3 156.7(2) . . . . ?
C7 N2 C8 N3 -16.1(4) . . . . ?
C1 N2 C8 N4 -24.4(4) . . . . ?
C7 N2 C8 N4 162.9(2) . . . . ?
C8 N3 C9 C10 0.7(4) . . . . ?
N3 C9 C10 C11 -3.3(4) . . . . ?
C8 N4 C11 C10 2.0(4) . . . . ?
Cu1 N4 C11 C10 -178.07(19) . . . . ?
C9 C10 C11 N4 1.8(4) . . . . ?

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.097
_shelxl_version_number           2014-3
