# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_khd318h
_audit_block_doi                 10.5517/ccdc.csd.cc1p59cj
_database_code_depnum_ccdc_archive 'CCDC 1554227'
loop_
_audit_author_name
_audit_author_address
'Behrouz Notash' 'Shahid Beheshti University'
_audit_update_record             
;
2018-02-23 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H11 Co N O9'
_chemical_formula_sum            'C7 H11 Co N O9'
_chemical_formula_weight         312.10

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'
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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.902(2)
_cell_length_b                   10.698(2)
_cell_length_c                   11.742(2)
_cell_angle_alpha                68.84(3)
_cell_angle_beta                 84.28(3)
_cell_angle_gamma                66.30(3)
_cell_volume                     1060.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5672
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      29.19

_exptl_crystal_description       needle
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.954
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636
_exptl_absorpt_coefficient_mu    1.663
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4902
_exptl_absorpt_correction_T_max  0.7321
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11589
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         29.19
_reflns_number_total             5672
_reflns_number_gt                3884
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0341P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5672
_refine_ls_number_parameters     371
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0716
_refine_ls_wR_factor_gt          0.0668
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_restrained_S_all      0.893
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.74028(3) 0.23834(3) -0.13170(3) 0.01808(8) Uani 1 1 d . . .
O10 O 0.56681(18) 0.41147(18) -0.10495(17) 0.0268(4) Uani 1 1 d . . .
O8 O 0.6946(2) 0.3432(2) -0.31820(16) 0.0331(4) Uani 1 1 d . . .
O7 O 0.91545(17) 0.06883(17) -0.16986(16) 0.0246(3) Uani 1 1 d D . .
O9 O 0.58784(18) 0.13952(19) -0.11574(16) 0.0268(4) Uani 1 1 d D . .
O1 O 0.80463(16) 0.12720(15) 0.05484(13) 0.0219(3) Uani 1 1 d . . .
O6 O 1.06598(19) 0.3189(2) -0.01853(17) 0.0431(5) Uani 1 1 d . . .
O5 O 0.88471(17) 0.33513(18) -0.12697(14) 0.0268(3) Uani 1 1 d . . .
O3 O 0.5927(2) 0.14194(18) 0.45272(16) 0.0331(4) Uani 1 1 d . . .
O4 O 0.52919(18) 0.37362(17) 0.43271(15) 0.0303(4) Uani 1 1 d . . .
N1 N 0.78765(18) 0.21528(18) 0.11916(15) 0.0179(3) Uani 1 1 d . . .
C7 C 0.9426(2) 0.3226(2) -0.0297(2) 0.0223(4) Uani 1 1 d . . .
C6 C 0.8517(2) 0.3128(2) 0.08320(19) 0.0189(4) Uani 1 1 d . . .
C4 C 0.7487(2) 0.3886(2) 0.2533(2) 0.0223(4) Uani 1 1 d . . .
H4 H 0.7332 0.4500 0.2970 0.027 Uiso 1 1 calc R . .
C5 C 0.8337(2) 0.3997(2) 0.1512(2) 0.0238(4) Uani 1 1 d . . .
H5 H 0.8786 0.4659 0.1287 0.029 Uiso 1 1 calc R . .
C2 C 0.6876(2) 0.2855(2) 0.28916(19) 0.0188(4) Uani 1 1 d . . .
C3 C 0.5954(2) 0.2658(2) 0.40094(19) 0.0212(4) Uani 1 1 d . . .
C1 C 0.7097(2) 0.1985(2) 0.22055(19) 0.0193(4) Uani 1 1 d . . .
H1 H 0.6706 0.1276 0.2445 0.023 Uiso 1 1 calc R . .
Co2 Co 0.23171(3) 0.24261(3) 0.65331(3) 0.01827(8) Uani 1 1 d . . .
O11 O 0.40164(19) 0.14749(18) 0.06625(16) 0.0346(4) Uani 1 1 d . . .
O12 O 0.40219(19) 0.34854(18) 0.08194(16) 0.0337(4) Uani 1 1 d . . .
O2 O 0.17073(16) 0.36628(15) 0.46883(13) 0.0225(3) Uani 1 1 d . . .
O13 O 0.08114(17) 0.15302(18) 0.64281(14) 0.0285(4) Uani 1 1 d . . .
O14 O -0.11429(18) 0.2114(2) 0.52677(16) 0.0364(4) Uani 1 1 d . . .
O16 O 0.2593(2) 0.1359(2) 0.84422(16) 0.0307(4) Uani 1 1 d . . .
O17 O 0.06196(19) 0.41449(18) 0.68795(17) 0.0283(4) Uani 1 1 d . . .
O15 O 0.38966(18) 0.32515(18) 0.65071(16) 0.0273(4) Uani 1 1 d . . .
H15A H 0.4457 0.2744 0.7117 0.033 Uiso 1 1 calc R . .
O18 O 0.40296(19) 0.07182(18) 0.61805(17) 0.0279(4) Uani 1 1 d . . .
N2 N 0.18102(18) 0.28609(18) 0.39983(16) 0.0182(3) Uani 1 1 d . . .
C14 C 0.0153(2) 0.1896(2) 0.5420(2) 0.0227(4) Uani 1 1 d . . .
C13 C 0.1069(2) 0.1977(2) 0.42920(19) 0.0204(4) Uani 1 1 d . . .
C12 C 0.1155(2) 0.1198(2) 0.3559(2) 0.0260(5) Uani 1 1 d . . .
H12 H 0.0637 0.0598 0.3741 0.031 Uiso 1 1 calc R . .
C11 C 0.2013(2) 0.1305(2) 0.2549(2) 0.0250(5) Uani 1 1 d . . .
H11 H 0.2102 0.0749 0.2071 0.030 Uiso 1 1 calc R . .
C9 C 0.2735(2) 0.2238(2) 0.22549(19) 0.0202(4) Uani 1 1 d . . .
C8 C 0.2607(2) 0.3025(2) 0.29939(19) 0.0197(4) Uani 1 1 d . . .
H8 H 0.3072 0.3672 0.2800 0.024 Uiso 1 1 calc R . .
C10 C 0.3666(2) 0.2417(2) 0.1152(2) 0.0224(4) Uani 1 1 d . . .
H7B H 0.959(3) 0.098(3) -0.232(3) 0.027 Uiso 1 1 d . . .
H17A H 0.022(3) 0.392(3) 0.748(3) 0.027 Uiso 1 1 d . . .
H18A H 0.384(3) 0.021(3) 0.596(3) 0.027 Uiso 1 1 d . . .
H7A H 0.975(2) 0.020(3) -0.117(2) 0.027 Uiso 1 1 d D . .
H8A H 0.638(3) 0.416(3) -0.346(3) 0.027 Uiso 1 1 d . . .
H9A H 0.533(3) 0.149(3) -0.068(3) 0.027 Uiso 1 1 d . . .
H17B H 0.004(3) 0.462(3) 0.632(3) 0.027 Uiso 1 1 d . . .
H16B H 0.248(3) 0.067(3) 0.873(3) 0.027 Uiso 1 1 d . . .
H9B H 0.601(3) 0.063(2) -0.116(2) 0.027 Uiso 1 1 d D . .
H8B H 0.740(3) 0.311(3) -0.370(3) 0.027 Uiso 1 1 d . . .
H18B H 0.467(3) 0.098(3) 0.571(2) 0.027 Uiso 1 1 d . . .
H10A H 0.505(3) 0.395(3) -0.050(3) 0.027 Uiso 1 1 d . . .
H10B H 0.585(3) 0.470(3) -0.104(3) 0.027 Uiso 1 1 d . . .
H16A H 0.223(3) 0.182(3) 0.886(3) 0.027 Uiso 1 1 d . . .
H15B H 0.438(3) 0.338(3) 0.583(2) 0.027 Uiso 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
Co1 O10 2.0578(18) . ?
Co1 O8 2.0674(19) . ?
Co1 O5 2.0901(17) . ?
Co1 O7 2.0978(17) . ?
Co1 O1 2.0991(17) . ?
Co1 O9 2.1248(18) . ?
O10 H10A 0.86(3) . ?
O10 H10B 0.73(3) . ?
O8 H8A 0.72(3) . ?
O8 H8B 0.81(3) . ?
O7 H7B 0.83(3) . ?
O7 H7A 0.767(16) . ?
O9 H9A 0.75(3) . ?
O9 H9B 0.776(16) . ?
O1 N1 1.359(2) . ?
O6 C7 1.225(3) . ?
O5 C7 1.268(3) . ?
O3 C3 1.254(3) . ?
O4 C3 1.246(2) . ?
N1 C1 1.349(3) . ?
N1 C6 1.353(3) . ?
C7 C6 1.522(3) . ?
C6 C5 1.381(3) . ?
C4 C2 1.382(3) . ?
C4 C5 1.391(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C2 C1 1.380(3) . ?
C2 C3 1.522(3) . ?
C1 H1 0.9300 . ?
Co2 O17 2.0714(18) . ?
Co2 O18 2.0738(17) . ?
Co2 O15 2.0756(17) . ?
Co2 O2 2.0873(17) . ?
Co2 O16 2.1039(19) . ?
Co2 O13 2.1041(17) . ?
O11 C10 1.251(3) . ?
O12 C10 1.248(3) . ?
O2 N2 1.348(2) . ?
O13 C14 1.263(3) . ?
O14 C14 1.228(3) . ?
O16 H16B 0.74(3) . ?
O16 H16A 0.78(3) . ?
O17 H17A 0.78(3) . ?
O17 H17B 0.78(3) . ?
O15 H15A 0.8200 . ?
O15 H15B 0.89(3) . ?
O18 H18A 0.76(3) . ?
O18 H18B 0.86(3) . ?
N2 C8 1.349(3) . ?
N2 C13 1.350(3) . ?
C14 C13 1.524(3) . ?
C13 C12 1.375(3) . ?
C12 C11 1.386(3) . ?
C12 H12 0.9300 . ?
C11 C9 1.380(3) . ?
C11 H11 0.9300 . ?
C9 C8 1.377(3) . ?
C9 C10 1.512(3) . ?
C8 H8 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
O10 Co1 O8 88.94(8) . . ?
O10 Co1 O5 89.76(7) . . ?
O8 Co1 O5 93.45(8) . . ?
O10 Co1 O7 176.68(7) . . ?
O8 Co1 O7 87.78(8) . . ?
O5 Co1 O7 90.01(7) . . ?
O10 Co1 O1 94.50(8) . . ?
O8 Co1 O1 175.41(7) . . ?
O5 Co1 O1 83.53(7) . . ?
O7 Co1 O1 88.76(7) . . ?
O10 Co1 O9 87.04(7) . . ?
O8 Co1 O9 92.22(8) . . ?
O5 Co1 O9 173.43(7) . . ?
O7 Co1 O9 93.52(7) . . ?
O1 Co1 O9 91.00(7) . . ?
Co1 O10 H10A 119.4(16) . . ?
Co1 O10 H10B 115(2) . . ?
H10A O10 H10B 111(3) . . ?
Co1 O8 H8A 124(2) . . ?
Co1 O8 H8B 125.0(18) . . ?
H8A O8 H8B 111(3) . . ?
Co1 O7 H7B 113.2(17) . . ?
Co1 O7 H7A 114.3(19) . . ?
H7B O7 H7A 107(3) . . ?
Co1 O9 H9A 116(2) . . ?
Co1 O9 H9B 130(2) . . ?
H9A O9 H9B 103(3) . . ?
N1 O1 Co1 114.44(11) . . ?
C7 O5 Co1 124.37(14) . . ?
C1 N1 C6 121.93(18) . . ?
C1 N1 O1 117.90(17) . . ?
C6 N1 O1 120.14(16) . . ?
O6 C7 O5 125.6(2) . . ?
O6 C7 C6 116.5(2) . . ?
O5 C7 C6 117.86(19) . . ?
N1 C6 C5 118.77(18) . . ?
N1 C6 C7 119.28(19) . . ?
C5 C6 C7 121.95(19) . . ?
C2 C4 C5 119.4(2) . . ?
C2 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C1 C2 C4 118.85(19) . . ?
C1 C2 C3 118.95(19) . . ?
C4 C2 C3 122.20(19) . . ?
O4 C3 O3 125.8(2) . . ?
O4 C3 C2 117.53(19) . . ?
O3 C3 C2 116.71(18) . . ?
N1 C1 C2 120.63(19) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
O17 Co2 O18 179.41(8) . . ?
O17 Co2 O15 93.74(7) . . ?
O18 Co2 O15 85.69(7) . . ?
O17 Co2 O2 85.74(7) . . ?
O18 Co2 O2 94.10(8) . . ?
O15 Co2 O2 91.77(7) . . ?
O17 Co2 O16 86.27(8) . . ?
O18 Co2 O16 93.93(8) . . ?
O15 Co2 O16 92.55(8) . . ?
O2 Co2 O16 171.15(6) . . ?
O17 Co2 O13 90.30(7) . . ?
O18 Co2 O13 90.25(7) . . ?
O15 Co2 O13 174.82(7) . . ?
O2 Co2 O13 85.31(7) . . ?
O16 Co2 O13 90.94(8) . . ?
N2 O2 Co2 113.71(11) . . ?
C14 O13 Co2 120.18(14) . . ?
Co2 O16 H16B 120(2) . . ?
Co2 O16 H16A 119(2) . . ?
H16B O16 H16A 106(3) . . ?
Co2 O17 H17A 114.9(18) . . ?
Co2 O17 H17B 111.5(19) . . ?
H17A O17 H17B 110(3) . . ?
Co2 O15 H15A 109.5 . . ?
Co2 O15 H15B 114.7(17) . . ?
H15A O15 H15B 111.8 . . ?
Co2 O18 H18A 119(2) . . ?
Co2 O18 H18B 113.7(16) . . ?
H18A O18 H18B 109(3) . . ?
O2 N2 C8 118.17(17) . . ?
O2 N2 C13 119.75(16) . . ?
C8 N2 C13 122.01(18) . . ?
O14 C14 O13 126.1(2) . . ?
O14 C14 C13 116.3(2) . . ?
O13 C14 C13 117.40(19) . . ?
N2 C13 C12 118.92(19) . . ?
N2 C13 C14 118.55(19) . . ?
C12 C13 C14 122.52(19) . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C9 C11 C12 119.8(2) . . ?
C9 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C8 C9 C11 118.80(19) . . ?
C8 C9 C10 119.17(19) . . ?
C11 C9 C10 122.0(2) . . ?
N2 C8 C9 120.3(2) . . ?
N2 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
O12 C10 O11 126.0(2) . . ?
O12 C10 C9 117.00(19) . . ?
O11 C10 C9 117.0(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
O10 Co1 O1 N1 -35.63(13) . . . . ?
O8 Co1 O1 N1 102.8(8) . . . . ?
O5 Co1 O1 N1 53.62(12) . . . . ?
O7 Co1 O1 N1 143.77(13) . . . . ?
O9 Co1 O1 N1 -122.73(13) . . . . ?
O10 Co1 O5 C7 84.42(18) . . . . ?
O8 Co1 O5 C7 173.34(17) . . . . ?
O7 Co1 O5 C7 -98.89(18) . . . . ?
O1 Co1 O5 C7 -10.14(17) . . . . ?
O9 Co1 O5 C7 23.7(7) . . . . ?
Co1 O1 N1 C1 126.62(15) . . . . ?
Co1 O1 N1 C6 -55.4(2) . . . . ?
Co1 O5 C7 O6 146.4(2) . . . . ?
Co1 O5 C7 C6 -34.3(3) . . . . ?
C1 N1 C6 C5 -1.4(3) . . . . ?
O1 N1 C6 C5 -179.31(18) . . . . ?
C1 N1 C6 C7 177.89(18) . . . . ?
O1 N1 C6 C7 0.0(3) . . . . ?
O6 C7 C6 N1 -130.0(2) . . . . ?
O5 C7 C6 N1 50.7(3) . . . . ?
O6 C7 C6 C5 49.3(3) . . . . ?
O5 C7 C6 C5 -130.1(2) . . . . ?
N1 C6 C5 C4 -1.3(3) . . . . ?
C7 C6 C5 C4 179.4(2) . . . . ?
C2 C4 C5 C6 2.7(3) . . . . ?
C5 C4 C2 C1 -1.5(3) . . . . ?
C5 C4 C2 C3 179.1(2) . . . . ?
C1 C2 C3 O4 -152.7(2) . . . . ?
C4 C2 C3 O4 26.7(3) . . . . ?
C1 C2 C3 O3 27.1(3) . . . . ?
C4 C2 C3 O3 -153.5(2) . . . . ?
C6 N1 C1 C2 2.6(3) . . . . ?
O1 N1 C1 C2 -179.43(17) . . . . ?
C4 C2 C1 N1 -1.1(3) . . . . ?
C3 C2 C1 N1 178.33(18) . . . . ?
O17 Co2 O2 N2 -142.78(13) . . . . ?
O18 Co2 O2 N2 37.79(13) . . . . ?
O15 Co2 O2 N2 123.60(13) . . . . ?
O16 Co2 O2 N2 -117.3(4) . . . . ?
O13 Co2 O2 N2 -52.12(12) . . . . ?
O17 Co2 O13 C14 89.03(17) . . . . ?
O18 Co2 O13 C14 -90.76(17) . . . . ?
O15 Co2 O13 C14 -52.4(8) . . . . ?
O2 Co2 O13 C14 3.34(16) . . . . ?
O16 Co2 O13 C14 175.31(17) . . . . ?
Co2 O2 N2 C8 -126.52(16) . . . . ?
Co2 O2 N2 C13 56.5(2) . . . . ?
Co2 O13 C14 O14 -140.6(2) . . . . ?
Co2 O13 C14 C13 43.9(2) . . . . ?
O2 N2 C13 C12 178.26(19) . . . . ?
C8 N2 C13 C12 1.4(3) . . . . ?
O2 N2 C13 C14 -1.1(3) . . . . ?
C8 N2 C13 C14 -177.95(18) . . . . ?
O14 C14 C13 N2 127.0(2) . . . . ?
O13 C14 C13 N2 -57.0(3) . . . . ?
O14 C14 C13 C12 -52.3(3) . . . . ?
O13 C14 C13 C12 123.7(2) . . . . ?
N2 C13 C12 C11 1.1(3) . . . . ?
C14 C13 C12 C11 -179.5(2) . . . . ?
C13 C12 C11 C9 -2.5(3) . . . . ?
C12 C11 C9 C8 1.3(3) . . . . ?
C12 C11 C9 C10 -179.0(2) . . . . ?
O2 N2 C8 C9 -179.47(17) . . . . ?
C13 N2 C8 C9 -2.6(3) . . . . ?
C11 C9 C8 N2 1.2(3) . . . . ?
C10 C9 C8 N2 -178.51(18) . . . . ?
C8 C9 C10 O12 -14.6(3) . . . . ?
C11 C9 C10 O12 165.7(2) . . . . ?
C8 C9 C10 O11 165.0(2) . . . . ?
C11 C9 C10 O11 -14.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        29.19
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.079
####################################################################### 
# 
# 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_khc1019b
_database_code_depnum_ccdc_archive 'CCDC 1554222'
_audit_update_record             
;
2017-06-04 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 Co N3 O7, 4(H2 O)'
_chemical_formula_sum            'C17 H23 Co N3 O11'
_chemical_formula_weight         504.31

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3305(19)
_cell_length_b                   9.882(2)
_cell_length_c                   11.820(2)
_cell_angle_alpha                83.25(3)
_cell_angle_beta                 78.22(3)
_cell_angle_gamma                89.16(3)
_cell_volume                     1059.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5672
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      29.17

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             522
_exptl_absorpt_coefficient_mu    0.875
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_T_max  0.6687
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11927
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         29.17
_reflns_number_total             5672
_reflns_number_gt                4795
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0652P)²+0.2433P] 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         5672
_refine_ls_number_parameters     325
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1162
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.75304(3) 0.80317(3) 0.79488(2) 0.02719(9) Uani 1 1 d . . .
O1 O 0.92447(16) 0.85460(16) 0.65117(12) 0.0337(3) Uani 1 1 d . . .
O2 O 1.14392(18) 0.55376(17) 0.36848(15) 0.0421(4) Uani 1 1 d . . .
O3 O 0.9871(2) 0.53808(19) 0.25265(16) 0.0509(4) Uani 1 1 d . . .
O4 O 0.63245(19) 0.93745(17) 0.70243(13) 0.0413(4) Uani 1 1 d . . .
O5 O 0.6385(2) 1.08112(18) 0.54201(15) 0.0501(4) Uani 1 1 d . . .
O6 O 0.68632(19) 0.64231(17) 0.71873(15) 0.0401(4) Uani 1 1 d . . .
O7 O 0.89211(19) 0.66635(16) 0.86919(14) 0.0385(3) Uani 1 1 d D . .
O8 O 0.3947(4) 0.6234(3) 0.4575(3) 0.0966(10) Uani 1 1 d D . .
O9 O 0.7969(3) 0.5691(3) 0.10000(18) 0.0652(6) Uani 1 1 d D . .
O10 O 0.7710(3) 0.1888(3) 0.3142(2) 0.0784(7) Uani 1 1 d D . .
O11 O 0.4059(3) 0.5793(3) 0.7062(2) 0.0773(8) Uani 1 1 d D . .
N1 N 0.88798(18) 0.82340(16) 0.55344(13) 0.0276(3) Uani 1 1 d . . .
N2 N 0.58939(19) 0.77551(17) 0.94871(15) 0.0302(3) Uani 1 1 d . . .
N3 N 0.80512(19) 0.95624(17) 0.89023(14) 0.0301(3) Uani 1 1 d . . .
C1 C 0.9726(2) 0.7351(2) 0.49150(16) 0.0288(4) Uani 1 1 d . . .
H1 H 1.0583 0.7037 0.5138 0.035 Uiso 1 1 calc R . .
C2 C 0.9338(2) 0.69083(19) 0.39528(16) 0.0288(4) Uani 1 1 d . . .
C3 C 1.0298(2) 0.5857(2) 0.33342(16) 0.0307(4) Uani 1 1 d . . .
C4 C 0.8075(3) 0.7412(2) 0.36189(18) 0.0366(4) Uani 1 1 d . . .
H4 H 0.7776 0.7109 0.2987 0.044 Uiso 1 1 calc R . .
C5 C 0.7259(3) 0.8370(2) 0.42350(18) 0.0376(5) Uani 1 1 d . . .
H5 H 0.6437 0.8745 0.3991 0.045 Uiso 1 1 calc R . .
C6 C 0.7658(2) 0.8772(2) 0.52072(16) 0.0310(4) Uani 1 1 d . . .
C7 C 0.6726(2) 0.9744(2) 0.59575(18) 0.0342(4) Uani 1 1 d . . .
C8 C 0.4842(3) 0.6786(2) 0.9736(2) 0.0400(5) Uani 1 1 d . . .
H8 H 0.4744 0.6244 0.9163 0.048 Uiso 1 1 calc R . .
C9 C 0.3898(3) 0.6561(3) 1.0810(2) 0.0483(6) Uani 1 1 d . . .
H9 H 0.3189 0.5875 1.0960 0.058 Uiso 1 1 calc R . .
C10 C 0.4034(3) 0.7376(3) 1.1651(2) 0.0490(6) Uani 1 1 d . . .
H10 H 0.3410 0.7252 1.2378 0.059 Uiso 1 1 calc R . .
C11 C 0.5097(3) 0.8370(3) 1.14097(19) 0.0419(5) Uani 1 1 d . . .
H11 H 0.5198 0.8927 1.1971 0.050 Uiso 1 1 calc R . .
C12 C 0.6028(2) 0.85425(19) 1.03145(16) 0.0296(4) Uani 1 1 d . . .
C13 C 0.7204(2) 0.9591(2) 0.99736(16) 0.0300(4) Uani 1 1 d . . .
C14 C 0.7439(3) 1.0548(2) 1.06888(19) 0.0396(5) Uani 1 1 d . . .
H14 H 0.6855 1.0550 1.1427 0.048 Uiso 1 1 calc R . .
C15 C 0.8559(3) 1.1501(2) 1.0284(2) 0.0456(5) Uani 1 1 d . . .
H15 H 0.8734 1.2153 1.0748 0.055 Uiso 1 1 calc R . .
C16 C 0.9407(3) 1.1469(2) 0.9191(2) 0.0442(5) Uani 1 1 d . . .
H16 H 1.0159 1.2101 0.8903 0.053 Uiso 1 1 calc R . .
C17 C 0.9125(3) 1.0483(2) 0.8527(2) 0.0378(4) Uani 1 1 d . . .
H17 H 0.9705 1.0461 0.7790 0.045 Uiso 1 1 calc R . .
H6A H 0.737(4) 0.578(4) 0.691(3) 0.057 Uiso 1 1 d . . .
H7A H 0.923(4) 0.609(4) 0.832(3) 0.057 Uiso 1 1 d . . .
H8A H 0.313(3) 0.587(3) 0.441(3) 0.057 Uiso 1 1 d D . .
H9A H 0.860(3) 0.561(3) 0.141(2) 0.057 Uiso 1 1 d D . .
H10A H 0.864(2) 0.193(3) 0.304(3) 0.057 Uiso 1 1 d D . .
H11A H 0.407(4) 0.570(3) 0.6349(17) 0.057 Uiso 1 1 d D . .
H6B H 0.603(4) 0.630(3) 0.712(3) 0.057 Uiso 1 1 d . . .
H7B H 0.858(3) 0.630(3) 0.9364(18) 0.057 Uiso 1 1 d D . .
H8B H 0.407(4) 0.7179(19) 0.449(3) 0.057 Uiso 1 1 d D . .
H9B H 0.729(3) 0.533(3) 0.153(2) 0.057 Uiso 1 1 d D . .
H10B H 0.731(3) 0.144(3) 0.381(2) 0.057 Uiso 1 1 d D . .
H11B H 0.336(3) 0.637(3) 0.710(3) 0.057 Uiso 1 1 d D . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O6 2.0782(16) . ?
Co1 O4 2.0829(17) . ?
Co1 O1 2.1009(17) . ?
Co1 O7 2.1019(17) . ?
Co1 N3 2.1072(17) . ?
Co1 N2 2.1153(18) . ?
O1 N1 1.339(2) . ?
O2 C3 1.243(3) . ?
O3 C3 1.248(3) . ?
O4 C7 1.252(3) . ?
O5 C7 1.238(3) . ?
O6 H6A 0.85(4) . ?
O6 H6B 0.81(4) . ?
O7 H7A 0.78(4) . ?
O7 H7B 0.834(18) . ?
O8 H8A 0.915(18) . ?
O8 H8A 0.915(18) . ?
O8 H8B 0.933(18) . ?
O9 H9A 0.832(17) . ?
O9 H9A 0.832(17) . ?
O9 H9B 0.847(17) . ?
O10 H10A 0.854(18) . ?
O10 H10B 0.872(18) . ?
O11 H11A 0.855(18) . ?
O11 H11B 0.860(18) . ?
N1 C1 1.347(2) . ?
N1 C6 1.358(3) . ?
N2 C12 1.345(3) . ?
N2 C8 1.346(3) . ?
N3 C17 1.334(3) . ?
N3 C13 1.352(3) . ?
C1 C2 1.381(3) . ?
C1 H1 0.9300 . ?
C2 C4 1.386(3) . ?
C2 C3 1.516(3) . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.525(3) . ?
C8 C9 1.386(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.398(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.481(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.388(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(3) . ?
C16 H16 0.9300 . ?
C17 H17 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
O6 Co1 O4 90.02(7) . . ?
O6 Co1 O1 91.72(7) . . ?
O4 Co1 O1 84.01(7) . . ?
O6 Co1 O7 87.87(7) . . ?
O4 Co1 O7 173.18(6) . . ?
O1 Co1 O7 89.57(7) . . ?
O6 Co1 N3 173.36(7) . . ?
O4 Co1 N3 92.25(7) . . ?
O1 Co1 N3 94.72(7) . . ?
O7 Co1 N3 90.55(7) . . ?
O6 Co1 N2 96.20(7) . . ?
O4 Co1 N2 95.41(7) . . ?
O1 Co1 N2 172.06(6) . . ?
O7 Co1 N2 91.27(7) . . ?
N3 Co1 N2 77.38(7) . . ?
N1 O1 Co1 110.49(11) . . ?
C7 O4 Co1 122.60(14) . . ?
Co1 O6 H6A 129(2) . . ?
Co1 O6 H6B 124(2) . . ?
H6A O6 H6B 107(3) . . ?
Co1 O7 H7A 115(2) . . ?
Co1 O7 H7B 116(2) . . ?
H7A O7 H7B 107(3) . . ?
H8A O8 H8A 0(4) . . ?
H8A O8 H8B 119(3) . . ?
H8A O8 H8B 119(3) . . ?
H9A O9 H9A 0(3) . . ?
H9A O9 H9B 95(2) . . ?
H9A O9 H9B 95(2) . . ?
H10A O10 H10B 112(3) . . ?
H11A O11 H11B 93(3) . . ?
O1 N1 C1 118.33(16) . . ?
O1 N1 C6 120.05(15) . . ?
C1 N1 C6 121.58(17) . . ?
C12 N2 C8 118.56(18) . . ?
C12 N2 Co1 115.68(14) . . ?
C8 N2 Co1 125.44(15) . . ?
C17 N3 C13 118.98(18) . . ?
C17 N3 Co1 125.21(14) . . ?
C13 N3 Co1 115.81(14) . . ?
N1 C1 C2 120.83(18) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C4 118.72(17) . . ?
C1 C2 C3 118.06(17) . . ?
C4 C2 C3 123.19(18) . . ?
O2 C3 O3 125.68(19) . . ?
O2 C3 C2 116.86(18) . . ?
O3 C3 C2 117.46(19) . . ?
C2 C4 C5 119.44(19) . . ?
C2 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N1 C6 C5 118.87(17) . . ?
N1 C6 C7 119.19(17) . . ?
C5 C6 C7 121.86(18) . . ?
O5 C7 O4 126.47(19) . . ?
O5 C7 C6 115.13(18) . . ?
O4 C7 C6 118.30(18) . . ?
N2 C8 C9 122.7(2) . . ?
N2 C8 H8 118.6 . . ?
C9 C8 H8 118.6 . . ?
C10 C9 C8 118.5(2) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C11 C10 C9 119.5(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 119.6(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
N2 C12 C11 121.2(2) . . ?
N2 C12 C13 115.40(17) . . ?
C11 C12 C13 123.42(19) . . ?
N3 C13 C14 121.4(2) . . ?
N3 C13 C12 115.39(17) . . ?
C14 C13 C12 123.25(19) . . ?
C13 C14 C15 119.0(2) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 119.2(2) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 119.0(2) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
N3 C17 C16 122.5(2) . . ?
N3 C17 H17 118.7 . . ?
C16 C17 H17 118.7 . . ?

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
O6 Co1 O1 N1 30.73(13) . . . . ?
O4 Co1 O1 N1 -59.12(12) . . . . ?
O7 Co1 O1 N1 118.59(12) . . . . ?
N3 Co1 O1 N1 -150.89(12) . . . . ?
N2 Co1 O1 N1 -145.3(4) . . . . ?
O6 Co1 O4 C7 -74.17(19) . . . . ?
O1 Co1 O4 C7 17.56(18) . . . . ?
O7 Co1 O4 C7 -2.1(7) . . . . ?
N3 Co1 O4 C7 112.07(19) . . . . ?
N2 Co1 O4 C7 -170.40(18) . . . . ?
Co1 O1 N1 C1 -120.85(15) . . . . ?
Co1 O1 N1 C6 57.2(2) . . . . ?
O6 Co1 N2 C12 173.16(14) . . . . ?
O4 Co1 N2 C12 -96.23(15) . . . . ?
O1 Co1 N2 C12 -10.8(5) . . . . ?
O7 Co1 N2 C12 85.16(14) . . . . ?
N3 Co1 N2 C12 -5.13(14) . . . . ?
O6 Co1 N2 C8 -0.16(19) . . . . ?
O4 Co1 N2 C8 90.45(18) . . . . ?
O1 Co1 N2 C8 175.8(4) . . . . ?
O7 Co1 N2 C8 -88.16(18) . . . . ?
N3 Co1 N2 C8 -178.44(19) . . . . ?
O6 Co1 N3 C17 168.3(5) . . . . ?
O4 Co1 N3 C17 -81.75(18) . . . . ?
O1 Co1 N3 C17 2.41(18) . . . . ?
O7 Co1 N3 C17 92.03(18) . . . . ?
N2 Co1 N3 C17 -176.79(18) . . . . ?
O6 Co1 N3 C13 -12.1(7) . . . . ?
O4 Co1 N3 C13 97.85(14) . . . . ?
O1 Co1 N3 C13 -177.98(14) . . . . ?
O7 Co1 N3 C13 -88.37(14) . . . . ?
N2 Co1 N3 C13 2.81(13) . . . . ?
O1 N1 C1 C2 174.75(17) . . . . ?
C6 N1 C1 C2 -3.3(3) . . . . ?
N1 C1 C2 C4 1.4(3) . . . . ?
N1 C1 C2 C3 -176.78(17) . . . . ?
C1 C2 C3 O2 -5.3(3) . . . . ?
C4 C2 C3 O2 176.6(2) . . . . ?
C1 C2 C3 O3 174.2(2) . . . . ?
C4 C2 C3 O3 -3.9(3) . . . . ?
C1 C2 C4 C5 1.8(3) . . . . ?
C3 C2 C4 C5 179.9(2) . . . . ?
C2 C4 C5 C6 -3.2(4) . . . . ?
O1 N1 C6 C5 -176.14(19) . . . . ?
C1 N1 C6 C5 1.9(3) . . . . ?
O1 N1 C6 C7 0.8(3) . . . . ?
C1 N1 C6 C7 178.77(18) . . . . ?
C4 C5 C6 N1 1.4(3) . . . . ?
C4 C5 C6 C7 -175.4(2) . . . . ?
Co1 O4 C7 O5 -155.1(2) . . . . ?
Co1 O4 C7 C6 28.6(3) . . . . ?
N1 C6 C7 O5 131.8(2) . . . . ?
C5 C6 C7 O5 -51.4(3) . . . . ?
N1 C6 C7 O4 -51.5(3) . . . . ?
C5 C6 C7 O4 125.3(2) . . . . ?
C12 N2 C8 C9 -0.4(3) . . . . ?
Co1 N2 C8 C9 172.76(18) . . . . ?
N2 C8 C9 C10 0.8(4) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C8 N2 C12 C11 -0.3(3) . . . . ?
Co1 N2 C12 C11 -174.08(15) . . . . ?
C8 N2 C12 C13 -179.68(18) . . . . ?
Co1 N2 C12 C13 6.5(2) . . . . ?
C10 C11 C12 N2 0.5(3) . . . . ?
C10 C11 C12 C13 179.9(2) . . . . ?
C17 N3 C13 C14 -0.6(3) . . . . ?
Co1 N3 C13 C14 179.81(16) . . . . ?
C17 N3 C13 C12 179.29(18) . . . . ?
Co1 N3 C13 C12 -0.3(2) . . . . ?
N2 C12 C13 N3 -4.1(3) . . . . ?
C11 C12 C13 N3 176.50(19) . . . . ?
N2 C12 C13 C14 175.74(19) . . . . ?
C11 C12 C13 C14 -3.6(3) . . . . ?
N3 C13 C14 C15 0.7(3) . . . . ?
C12 C13 C14 C15 -179.2(2) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C13 N3 C17 C16 0.0(3) . . . . ?
Co1 N3 C17 C16 179.59(17) . . . . ?
C15 C16 C17 N3 0.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        29.17
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.147
####################################################################### 
# 
# 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_khc1029b
_database_code_depnum_ccdc_archive 'CCDC 1554223'
_audit_update_record             
;
2017-06-04 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H11 N O9 Zn'
_chemical_formula_sum            'C7 H11 N O9 Zn'
_chemical_formula_weight         318.56

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.889(2)
_cell_length_b                   10.653(2)
_cell_length_c                   11.751(2)
_cell_angle_alpha                68.87(3)
_cell_angle_beta                 84.25(3)
_cell_angle_gamma                66.44(3)
_cell_volume                     1057.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5656
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      29.24

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.001
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    2.369
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3839
_exptl_absorpt_correction_T_max  0.6488
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11619
_diffrn_reflns_av_R_equivalents  0.1040
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         29.24
_reflns_number_total             5656
_reflns_number_gt                4212
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0709P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5656
_refine_ls_number_parameters     373
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1339
_refine_ls_wR_factor_gt          0.1217
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.26653(4) 0.75651(4) -0.15449(3) 0.01708(12) Uani 1 1 d . . .
Zn2 Zn 0.75974(4) 0.76151(4) 0.63378(3) 0.01698(12) Uani 1 1 d . . .
O5 O 0.4199(3) 0.8475(3) -0.1422(2) 0.0260(6) Uani 1 1 d . . .
O8 O 0.1086(3) 0.6750(3) -0.1501(3) 0.0260(6) Uani 1 1 d D . .
O18 O 0.9306(3) 0.5912(3) 0.6045(3) 0.0254(6) Uani 1 1 d D . .
O10 O 0.4378(3) 0.5853(3) -0.1883(3) 0.0264(6) Uani 1 1 d . . .
O7 O 0.0983(3) 0.9273(3) -0.1178(3) 0.0251(6) Uani 1 1 d . . .
O17 O 0.9133(3) 0.8609(3) 0.6160(3) 0.0239(5) Uani 1 1 d D . .
O16 O 0.8066(3) 0.6559(3) 0.8194(3) 0.0306(7) Uani 1 1 d . . .
O9 O 0.2405(3) 0.8632(3) -0.3433(2) 0.0265(6) Uani 1 1 d D . .
O13 O 0.6153(3) 0.6624(3) 0.6268(2) 0.0249(6) Uani 1 1 d . . .
N1 N 0.3195(3) 0.7118(3) 0.0994(3) 0.0164(5) Uani 1 1 d . . .
N2 N 0.7096(3) 0.7877(3) 0.3796(2) 0.0150(5) Uani 1 1 d . . .
O15 O 0.5854(3) 0.9284(3) 0.6714(2) 0.0219(5) Uani 1 1 d D . .
O14 O 0.4296(3) 0.6883(4) 0.5172(3) 0.0364(7) Uani 1 1 d . . .
O6 O 0.6156(3) 0.7850(4) -0.0261(3) 0.0345(7) Uani 1 1 d . . .
C7 C 0.4856(4) 0.8093(4) -0.0410(3) 0.0196(7) Uani 1 1 d . . .
C14 C 0.5553(4) 0.6806(4) 0.5294(3) 0.0202(7) Uani 1 1 d . . .
C13 C 0.6468(4) 0.6887(4) 0.4161(3) 0.0173(6) Uani 1 1 d . . .
C6 C 0.3933(4) 0.8013(4) 0.0710(3) 0.0183(7) Uani 1 1 d . . .
C1 C 0.2385(4) 0.6968(4) 0.1998(3) 0.0178(6) Uani 1 1 d . . .
H1 H 0.1915 0.6321 0.2191 0.021 Uiso 1 1 calc R . .
C2 C 0.2248(4) 0.7755(4) 0.2737(3) 0.0181(6) Uani 1 1 d . . .
C9 C 0.8118(4) 0.7156(4) 0.2109(3) 0.0178(6) Uani 1 1 d . . .
C12 C 0.6657(4) 0.6000(4) 0.3487(3) 0.0214(7) Uani 1 1 d . . .
H12 H 0.6208 0.5333 0.3715 0.026 Uiso 1 1 calc R . .
C5 C 0.3832(4) 0.8806(4) 0.1439(3) 0.0239(7) Uani 1 1 d . . .
H5 H 0.4349 0.9410 0.1257 0.029 Uiso 1 1 calc R . .
C11 C 0.7511(4) 0.6104(4) 0.2476(3) 0.0215(7) Uani 1 1 d . . .
H11 H 0.7678 0.5478 0.2047 0.026 Uiso 1 1 calc R . .
C4 C 0.2963(4) 0.8708(4) 0.2440(3) 0.0225(7) Uani 1 1 d . . .
H4 H 0.2860 0.9278 0.2911 0.027 Uiso 1 1 calc R . .
O12 O 0.9714(3) 0.6259(3) 0.0681(2) 0.0265(6) Uani 1 1 d . . .
O3 O 0.0944(3) 0.8538(3) 0.4309(3) 0.0308(6) Uani 1 1 d . . .
O11 O 0.9058(3) 0.8585(3) 0.0464(3) 0.0293(6) Uani 1 1 d . . .
O4 O 0.0963(4) 0.6502(3) 0.4175(3) 0.0313(6) Uani 1 1 d . . .
C10 C 0.9043(4) 0.7337(4) 0.0995(3) 0.0194(7) Uani 1 1 d . . .
C3 C 0.1309(4) 0.7582(4) 0.3839(3) 0.0205(7) Uani 1 1 d . . .
C8 C 0.7886(4) 0.8034(4) 0.2786(3) 0.0186(7) Uani 1 1 d . . .
H8 H 0.8277 0.8747 0.2544 0.022 Uiso 1 1 calc R . .
O1 O 0.3316(3) 0.6315(3) 0.0308(2) 0.0206(5) Uani 1 1 d . . .
O2 O 0.6907(3) 0.8766(2) 0.4442(2) 0.0200(5) Uani 1 1 d . . .
H16B H 0.889(5) 0.565(5) 0.846(4) 0.024 Uiso 1 1 d . . .
H7A H 0.119(5) 0.981(5) -0.099(5) 0.024 Uiso 1 1 d . . .
H10B H 0.497(5) 0.536(5) -0.124(5) 0.024 Uiso 1 1 d . . .
H18A H 0.978(5) 0.612(5) 0.550(5) 0.024 Uiso 1 1 d . . .
H7B H 0.045(5) 0.902(5) -0.072(5) 0.024 Uiso 1 1 d . . .
H18B H 0.917(5) 0.529(4) 0.588(4) 0.024 Uiso 1 1 d D . .
H10A H 0.493(5) 0.612(5) -0.255(5) 0.024 Uiso 1 1 d . . .
H17B H 0.914(5) 0.936(3) 0.615(4) 0.024 Uiso 1 1 d D . .
H16A H 0.763(5) 0.681(5) 0.875(5) 0.024 Uiso 1 1 d . . .
H17A H 0.973(5) 0.845(5) 0.558(5) 0.024 Uiso 1 1 d . . .
H9A H 0.290(5) 0.820(4) -0.389(3) 0.024 Uiso 1 1 d D . .
H8A H 0.049(4) 0.707(5) -0.205(3) 0.024 Uiso 1 1 d D . .
H8B H 0.063(5) 0.664(5) -0.087(5) 0.024 Uiso 1 1 d . . .
H15A H 0.521(5) 0.989(5) 0.624(5) 0.024 Uiso 1 1 d . . .
H15B H 0.543(4) 0.889(4) 0.726(3) 0.024 Uiso 1 1 d D . .
H9B H 0.245(5) 0.943(3) -0.371(4) 0.024 Uiso 1 1 d D . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O8 2.057(3) . ?
Zn1 O7 2.065(3) . ?
Zn1 O10 2.067(3) . ?
Zn1 O9 2.084(3) . ?
Zn1 O1 2.105(3) . ?
Zn1 O5 2.141(3) . ?
Zn2 O18 2.037(3) . ?
Zn2 O16 2.062(3) . ?
Zn2 O15 2.072(3) . ?
Zn2 O13 2.111(3) . ?
Zn2 O17 2.129(3) . ?
Zn2 O2 2.145(3) . ?
O5 C7 1.263(4) . ?
O8 H8A 0.805(19) . ?
O8 H8B 0.83(5) . ?
O18 H18A 0.77(5) . ?
O18 H18B 0.814(19) . ?
O10 H10B 0.87(5) . ?
O10 H10A 0.93(5) . ?
O7 H7A 0.78(5) . ?
O7 H7B 0.77(5) . ?
O17 H17B 0.802(19) . ?
O17 H17A 0.87(5) . ?
O16 H16B 0.95(5) . ?
O16 H16A 0.81(5) . ?
O9 H9A 0.829(19) . ?
O9 H9B 0.815(19) . ?
O13 C14 1.258(5) . ?
N1 O1 1.339(4) . ?
N1 C6 1.354(5) . ?
N1 C1 1.355(4) . ?
N2 C8 1.350(4) . ?
N2 C13 1.352(4) . ?
N2 O2 1.362(4) . ?
O15 H15A 0.78(5) . ?
O15 H15B 0.814(19) . ?
O14 C14 1.232(5) . ?
O6 C7 1.223(5) . ?
C7 C6 1.522(5) . ?
C14 C13 1.529(5) . ?
C13 C12 1.387(5) . ?
C6 C5 1.375(5) . ?
C1 C2 1.373(5) . ?
C1 H1 0.9300 . ?
C2 C4 1.386(5) . ?
C2 C3 1.516(5) . ?
C9 C8 1.375(5) . ?
C9 C11 1.393(5) . ?
C9 C10 1.519(5) . ?
C12 C11 1.384(5) . ?
C12 H12 0.9300 . ?
C5 C4 1.384(5) . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C4 H4 0.9300 . ?
O12 C10 1.242(4) . ?
O3 C3 1.243(5) . ?
O11 C10 1.255(4) . ?
O4 C3 1.248(5) . ?
C8 H8 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
O8 Zn1 O7 85.85(12) . . ?
O8 Zn1 O10 95.02(12) . . ?
O7 Zn1 O10 178.75(13) . . ?
O8 Zn1 O9 93.45(12) . . ?
O7 Zn1 O9 94.31(12) . . ?
O10 Zn1 O9 86.55(12) . . ?
O8 Zn1 O1 92.25(11) . . ?
O7 Zn1 O1 94.18(12) . . ?
O10 Zn1 O1 84.89(11) . . ?
O9 Zn1 O1 170.10(11) . . ?
O8 Zn1 O5 173.72(12) . . ?
O7 Zn1 O5 89.40(12) . . ?
O10 Zn1 O5 89.67(12) . . ?
O9 Zn1 O5 90.99(11) . . ?
O1 Zn1 O5 84.00(10) . . ?
O18 Zn2 O16 89.39(13) . . ?
O18 Zn2 O15 177.41(11) . . ?
O16 Zn2 O15 88.24(12) . . ?
O18 Zn2 O13 89.04(12) . . ?
O16 Zn2 O13 94.22(12) . . ?
O15 Zn2 O13 90.10(11) . . ?
O18 Zn2 O17 86.72(12) . . ?
O16 Zn2 O17 92.47(13) . . ?
O15 Zn2 O17 94.42(11) . . ?
O13 Zn2 O17 172.04(11) . . ?
O18 Zn2 O2 94.42(12) . . ?
O16 Zn2 O2 174.93(11) . . ?
O15 Zn2 O2 87.89(11) . . ?
O13 Zn2 O2 82.52(10) . . ?
O17 Zn2 O2 91.08(11) . . ?
C7 O5 Zn1 120.0(2) . . ?
Zn1 O8 H8A 123(3) . . ?
Zn1 O8 H8B 115(3) . . ?
H8A O8 H8B 106(5) . . ?
Zn2 O18 H18A 116(3) . . ?
Zn2 O18 H18B 122(3) . . ?
H18A O18 H18B 98(5) . . ?
Zn1 O10 H10B 108(3) . . ?
Zn1 O10 H10A 116(3) . . ?
H10B O10 H10A 108(4) . . ?
Zn1 O7 H7A 118(4) . . ?
Zn1 O7 H7B 113(3) . . ?
H7A O7 H7B 109(5) . . ?
Zn2 O17 H17B 139(3) . . ?
Zn2 O17 H17A 110(3) . . ?
H17B O17 H17A 102(4) . . ?
Zn2 O16 H16B 118(3) . . ?
Zn2 O16 H16A 129(3) . . ?
H16B O16 H16A 114(4) . . ?
Zn1 O9 H9A 120(3) . . ?
Zn1 O9 H9B 118(3) . . ?
H9A O9 H9B 105(5) . . ?
C14 O13 Zn2 123.7(2) . . ?
O1 N1 C6 119.8(3) . . ?
O1 N1 C1 119.1(3) . . ?
C6 N1 C1 120.9(3) . . ?
C8 N2 C13 121.6(3) . . ?
C8 N2 O2 118.7(3) . . ?
C13 N2 O2 119.7(3) . . ?
Zn2 O15 H15A 124(4) . . ?
Zn2 O15 H15B 106(3) . . ?
H15A O15 H15B 104(5) . . ?
O6 C7 O5 125.7(3) . . ?
O6 C7 C6 117.0(3) . . ?
O5 C7 C6 117.3(3) . . ?
O14 C14 O13 125.8(3) . . ?
O14 C14 C13 116.2(3) . . ?
O13 C14 C13 117.9(3) . . ?
N2 C13 C12 119.0(3) . . ?
N2 C13 C14 118.4(3) . . ?
C12 C13 C14 122.5(3) . . ?
N1 C6 C5 119.4(3) . . ?
N1 C6 C7 118.1(3) . . ?
C5 C6 C7 122.5(3) . . ?
N1 C1 C2 121.1(3) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C1 C2 C4 118.7(3) . . ?
C1 C2 C3 119.7(3) . . ?
C4 C2 C3 121.7(3) . . ?
C8 C9 C11 118.8(3) . . ?
C8 C9 C10 119.5(3) . . ?
C11 C9 C10 121.6(3) . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C12 C11 C9 119.3(3) . . ?
C12 C11 H11 120.4 . . ?
C9 C11 H11 120.4 . . ?
C5 C4 C2 119.5(3) . . ?
C5 C4 H4 120.3 . . ?
C2 C4 H4 120.3 . . ?
O12 C10 O11 125.4(3) . . ?
O12 C10 C9 118.3(3) . . ?
O11 C10 C9 116.3(3) . . ?
O3 C3 O4 126.4(3) . . ?
O3 C3 C2 116.9(3) . . ?
O4 C3 C2 116.7(3) . . ?
N2 C8 C9 120.9(3) . . ?
N2 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
N1 O1 Zn1 113.68(18) . . ?
N2 O2 Zn2 114.00(17) . . ?

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
O8 Zn1 O5 C7 50.1(11) . . . . ?
O7 Zn1 O5 C7 90.9(3) . . . . ?
O10 Zn1 O5 C7 -88.3(3) . . . . ?
O9 Zn1 O5 C7 -174.9(3) . . . . ?
O1 Zn1 O5 C7 -3.4(3) . . . . ?
O18 Zn2 O13 C14 -86.6(3) . . . . ?
O16 Zn2 O13 C14 -175.9(3) . . . . ?
O15 Zn2 O13 C14 95.9(3) . . . . ?
O17 Zn2 O13 C14 -28.8(9) . . . . ?
O2 Zn2 O13 C14 8.0(3) . . . . ?
Zn1 O5 C7 O6 139.2(3) . . . . ?
Zn1 O5 C7 C6 -44.6(4) . . . . ?
Zn2 O13 C14 O14 -143.9(3) . . . . ?
Zn2 O13 C14 C13 38.5(4) . . . . ?
C8 N2 C13 C12 0.8(5) . . . . ?
O2 N2 C13 C12 179.3(3) . . . . ?
C8 N2 C13 C14 -178.2(3) . . . . ?
O2 N2 C13 C14 0.3(4) . . . . ?
O14 C14 C13 N2 127.6(4) . . . . ?
O13 C14 C13 N2 -54.6(4) . . . . ?
O14 C14 C13 C12 -51.5(5) . . . . ?
O13 C14 C13 C12 126.4(4) . . . . ?
O1 N1 C6 C5 -178.3(3) . . . . ?
C1 N1 C6 C5 -1.5(5) . . . . ?
O1 N1 C6 C7 1.3(5) . . . . ?
C1 N1 C6 C7 178.2(3) . . . . ?
O6 C7 C6 N1 -125.5(4) . . . . ?
O5 C7 C6 N1 58.0(4) . . . . ?
O6 C7 C6 C5 54.2(5) . . . . ?
O5 C7 C6 C5 -122.3(4) . . . . ?
O1 N1 C1 C2 179.1(3) . . . . ?
C6 N1 C1 C2 2.2(5) . . . . ?
N1 C1 C2 C4 -0.3(5) . . . . ?
N1 C1 C2 C3 178.8(3) . . . . ?
N2 C13 C12 C11 1.8(5) . . . . ?
C14 C13 C12 C11 -179.2(3) . . . . ?
N1 C6 C5 C4 -1.1(5) . . . . ?
C7 C6 C5 C4 179.2(3) . . . . ?
C13 C12 C11 C9 -3.1(5) . . . . ?
C8 C9 C11 C12 1.9(5) . . . . ?
C10 C9 C11 C12 -179.0(3) . . . . ?
C6 C5 C4 C2 2.9(6) . . . . ?
C1 C2 C4 C5 -2.2(5) . . . . ?
C3 C2 C4 C5 178.7(3) . . . . ?
C8 C9 C10 O12 152.6(3) . . . . ?
C11 C9 C10 O12 -26.5(5) . . . . ?
C8 C9 C10 O11 -27.6(5) . . . . ?
C11 C9 C10 O11 153.3(4) . . . . ?
C1 C2 C3 O3 -164.0(3) . . . . ?
C4 C2 C3 O3 15.1(5) . . . . ?
C1 C2 C3 O4 15.1(5) . . . . ?
C4 C2 C3 O4 -165.8(4) . . . . ?
C13 N2 C8 C9 -2.0(5) . . . . ?
O2 N2 C8 C9 179.5(3) . . . . ?
C11 C9 C8 N2 0.6(5) . . . . ?
C10 C9 C8 N2 -178.5(3) . . . . ?
C6 N1 O1 Zn1 -58.2(3) . . . . ?
C1 N1 O1 Zn1 124.9(3) . . . . ?
O8 Zn1 O1 N1 -121.7(2) . . . . ?
O7 Zn1 O1 N1 -35.7(2) . . . . ?
O10 Zn1 O1 N1 143.4(2) . . . . ?
O9 Zn1 O1 N1 113.1(6) . . . . ?
O5 Zn1 O1 N1 53.2(2) . . . . ?
C8 N2 O2 Zn2 -125.2(3) . . . . ?
C13 N2 O2 Zn2 56.3(3) . . . . ?
O18 Zn2 O2 N2 34.4(2) . . . . ?
O16 Zn2 O2 N2 -104.3(13) . . . . ?
O15 Zn2 O2 N2 -144.5(2) . . . . ?
O13 Zn2 O2 N2 -54.1(2) . . . . ?
O17 Zn2 O2 N2 121.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        29.24
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         1.030
_refine_diff_density_min         -1.315
_refine_diff_density_rms         0.158
####################################################################### 
# 
# 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_khc1007b
_database_code_depnum_ccdc_archive 'CCDC 1554221'
_audit_update_record             
;
2017-06-04 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 Cl Cu N3 O5, 2(H2 O)'
_chemical_formula_sum            'C17 H16 Cl Cu N3 O7'
_chemical_formula_weight         473.33

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'
Cl Cl 0.1484 0.1585 '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
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5223(17)
_cell_length_b                   9.4697(19)
_cell_length_c                   12.214(2)
_cell_angle_alpha                75.25(3)
_cell_angle_beta                 84.25(3)
_cell_angle_gamma                80.60(3)
_cell_volume                     938.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5021
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      29.16

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             482
_exptl_absorpt_coefficient_mu    1.353
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6870
_exptl_absorpt_correction_T_max  0.9354
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10450
_diffrn_reflns_av_R_equivalents  0.1092
_diffrn_reflns_av_sigmaI/netI    0.1361
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         29.16
_reflns_number_total             5021
_reflns_number_gt                2868
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0508P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5021
_refine_ls_number_parameters     277
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1329
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.1388
_refine_ls_wR_factor_gt          0.1196
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.46999(7) 0.38526(6) 0.33530(5) 0.02921(17) Uani 1 1 d . . .
Cl1 Cl 0.25678(15) 0.25184(13) 0.31225(11) 0.0438(3) Uani 1 1 d . . .
O1 O 0.4648(4) 0.3384(3) 0.5011(3) 0.0334(7) Uani 1 1 d . . .
O2 O 0.2769(5) 0.0994(4) 0.8726(3) 0.0509(10) Uani 1 1 d . . .
O3 O 0.0349(5) 0.2150(4) 0.9075(3) 0.0580(10) Uani 1 1 d . . .
O4 O 0.3380(4) 0.5707(3) 0.3342(3) 0.0403(8) Uani 1 1 d . . .
O5 O 0.1820(4) 0.7367(3) 0.4086(3) 0.0448(9) Uani 1 1 d . . .
O6 O 0.2537(6) 0.9077(5) 0.0576(4) 0.0652(12) Uani 1 1 d D . .
O7 O 0.3496(6) 0.9394(5) 0.2538(4) 0.0619(12) Uani 1 1 d . . .
N1 N 0.3343(4) 0.3761(4) 0.5632(3) 0.0284(8) Uani 1 1 d . . .
N2 N 0.6557(5) 0.2269(4) 0.3349(3) 0.0315(9) Uani 1 1 d . . .
N3 N 0.5756(4) 0.4710(4) 0.1834(3) 0.0296(8) Uani 1 1 d . . .
C1 C 0.3132(6) 0.2827(5) 0.6656(4) 0.0326(10) Uani 1 1 d . . .
H1 H 0.3874 0.1989 0.6880 0.039 Uiso 1 1 calc R . .
C2 C 0.1830(5) 0.3104(5) 0.7370(4) 0.0322(10) Uani 1 1 d . . .
C3 C 0.1575(6) 0.2026(5) 0.8483(4) 0.0379(11) Uani 1 1 d . . .
C4 C 0.0741(6) 0.4371(5) 0.7035(4) 0.0388(11) Uani 1 1 d . . .
H4 H -0.0161 0.4566 0.7498 0.047 Uiso 1 1 calc R . .
C5 C 0.1021(6) 0.5333(5) 0.6006(4) 0.0360(11) Uani 1 1 d . . .
H5 H 0.0322 0.6204 0.5792 0.043 Uiso 1 1 calc R . .
C6 C 0.2318(5) 0.5033(4) 0.5285(4) 0.0306(10) Uani 1 1 d . . .
C7 C 0.2542(5) 0.6128(5) 0.4157(4) 0.0321(10) Uani 1 1 d . . .
C8 C 0.6853(6) 0.1064(5) 0.4177(4) 0.0411(12) Uani 1 1 d . . .
H8 H 0.6147 0.0913 0.4814 0.049 Uiso 1 1 calc R . .
C9 C 0.8182(6) 0.0026(5) 0.4117(5) 0.0423(12) Uani 1 1 d . . .
H9 H 0.8382 -0.0808 0.4709 0.051 Uiso 1 1 calc R . .
C10 C 0.9201(7) 0.0253(5) 0.3165(5) 0.0508(15) Uani 1 1 d . . .
H10 H 1.0104 -0.0429 0.3108 0.061 Uiso 1 1 calc R . .
C11 C 0.8889(6) 0.1482(5) 0.2301(5) 0.0427(12) Uani 1 1 d . . .
H11 H 0.9573 0.1642 0.1652 0.051 Uiso 1 1 calc R . .
C12 C 0.7535(5) 0.2486(5) 0.2408(4) 0.0312(10) Uani 1 1 d . . .
C13 C 0.7092(5) 0.3870(5) 0.1544(4) 0.0311(10) Uani 1 1 d . . .
C14 C 0.7930(6) 0.4321(5) 0.0527(4) 0.0416(12) Uani 1 1 d . . .
H14 H 0.8845 0.3735 0.0328 0.050 Uiso 1 1 calc R . .
C15 C 0.7402(7) 0.5643(6) -0.0191(5) 0.0509(14) Uani 1 1 d . . .
H15 H 0.7957 0.5956 -0.0884 0.061 Uiso 1 1 calc R . .
C16 C 0.6068(7) 0.6499(5) 0.0106(4) 0.0441(13) Uani 1 1 d . . .
H16 H 0.5708 0.7403 -0.0373 0.053 Uiso 1 1 calc R . .
C17 C 0.5255(6) 0.6000(5) 0.1135(4) 0.0391(12) Uani 1 1 d . . .
H17 H 0.4339 0.6578 0.1344 0.047 Uiso 1 1 calc R . .
H2 H 0.263(7) 0.034(6) 0.935(5) 0.059 Uiso 1 1 d . . .
H6A H 0.156(3) 0.896(6) 0.082(5) 0.059 Uiso 1 1 d D . .
H7A H 0.304(7) 1.015(7) 0.231(5) 0.059 Uiso 1 1 d . . .
H6B H 0.277(7) 0.930(6) 0.119(3) 0.059 Uiso 1 1 d D . .
H7B H 0.301(7) 0.880(6) 0.310(5) 0.059 Uiso 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 O4 1.922(3) . ?
Cu1 O1 1.957(3) . ?
Cu1 N2 1.995(3) . ?
Cu1 N3 2.012(4) . ?
Cu1 Cl1 2.4517(15) . ?
O1 N1 1.334(4) . ?
O2 C3 1.291(6) . ?
O2 H2 0.86(6) . ?
O3 C3 1.217(6) . ?
O4 C7 1.275(5) . ?
O5 C7 1.219(5) . ?
O6 H6A 0.87(2) . ?
O6 H6B 0.87(2) . ?
O7 H7A 0.76(6) . ?
O7 H7B 0.88(6) . ?
N1 C1 1.350(6) . ?
N1 C6 1.365(5) . ?
N2 C8 1.326(6) . ?
N2 C12 1.343(6) . ?
N3 C17 1.333(5) . ?
N3 C13 1.349(6) . ?
C1 C2 1.374(6) . ?
C1 H1 0.9300 . ?
C2 C4 1.389(6) . ?
C2 C3 1.498(7) . ?
C4 C5 1.376(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.515(7) . ?
C8 C9 1.383(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.479(6) . ?
C13 C14 1.373(7) . ?
C14 C15 1.370(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.359(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(7) . ?
C16 H16 0.9300 . ?
C17 H17 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
O4 Cu1 O1 90.15(13) . . ?
O4 Cu1 N2 163.81(16) . . ?
O1 Cu1 N2 89.56(14) . . ?
O4 Cu1 N3 91.14(14) . . ?
O1 Cu1 N3 149.97(15) . . ?
N2 Cu1 N3 81.14(15) . . ?
O4 Cu1 Cl1 96.66(12) . . ?
O1 Cu1 Cl1 99.30(11) . . ?
N2 Cu1 Cl1 99.36(12) . . ?
N3 Cu1 Cl1 110.33(11) . . ?
N1 O1 Cu1 121.8(2) . . ?
C3 O2 H2 115(4) . . ?
C7 O4 Cu1 129.0(3) . . ?
H6A O6 H6B 94(6) . . ?
H7A O7 H7B 116(7) . . ?
O1 N1 C1 115.4(3) . . ?
O1 N1 C6 122.7(4) . . ?
C1 N1 C6 121.8(4) . . ?
C8 N2 C12 120.1(4) . . ?
C8 N2 Cu1 125.2(3) . . ?
C12 N2 Cu1 114.8(3) . . ?
C17 N3 C13 119.8(4) . . ?
C17 N3 Cu1 125.7(3) . . ?
C13 N3 Cu1 114.6(3) . . ?
N1 C1 C2 120.5(4) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C1 C2 C4 119.3(4) . . ?
C1 C2 C3 120.0(4) . . ?
C4 C2 C3 120.7(4) . . ?
O3 C3 O2 125.2(5) . . ?
O3 C3 C2 121.6(4) . . ?
O2 C3 C2 113.2(4) . . ?
C5 C4 C2 118.9(4) . . ?
C5 C4 H4 120.6 . . ?
C2 C4 H4 120.6 . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
N1 C6 C5 118.0(4) . . ?
N1 C6 C7 123.3(4) . . ?
C5 C6 C7 118.7(4) . . ?
O5 C7 O4 124.4(4) . . ?
O5 C7 C6 115.7(4) . . ?
O4 C7 C6 119.9(4) . . ?
N2 C8 C9 121.7(5) . . ?
N2 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C10 C9 C8 118.5(5) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 118.9(5) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
N2 C12 C11 120.8(4) . . ?
N2 C12 C13 115.4(4) . . ?
C11 C12 C13 123.9(4) . . ?
N3 C13 C14 120.7(4) . . ?
N3 C13 C12 114.2(4) . . ?
C14 C13 C12 125.2(4) . . ?
C15 C14 C13 119.3(5) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C14 120.1(5) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 118.8(4) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
N3 C17 C16 121.4(5) . . ?
N3 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Cu1 O1 N1 37.0(3) . . . . ?
N2 Cu1 O1 N1 -159.2(3) . . . . ?
N3 Cu1 O1 N1 129.5(3) . . . . ?
Cl1 Cu1 O1 N1 -59.8(3) . . . . ?
O1 Cu1 O4 C7 -15.6(4) . . . . ?
N2 Cu1 O4 C7 -104.5(7) . . . . ?
N3 Cu1 O4 C7 -165.6(4) . . . . ?
Cl1 Cu1 O4 C7 83.8(4) . . . . ?
Cu1 O1 N1 C1 147.7(3) . . . . ?
Cu1 O1 N1 C6 -34.9(5) . . . . ?
O4 Cu1 N2 C8 117.4(6) . . . . ?
O1 Cu1 N2 C8 28.4(4) . . . . ?
N3 Cu1 N2 C8 179.7(4) . . . . ?
Cl1 Cu1 N2 C8 -70.9(4) . . . . ?
O4 Cu1 N2 C12 -63.5(7) . . . . ?
O1 Cu1 N2 C12 -152.5(3) . . . . ?
N3 Cu1 N2 C12 -1.1(3) . . . . ?
Cl1 Cu1 N2 C12 108.2(3) . . . . ?
O4 Cu1 N3 C17 -12.5(4) . . . . ?
O1 Cu1 N3 C17 -104.7(4) . . . . ?
N2 Cu1 N3 C17 -178.2(4) . . . . ?
Cl1 Cu1 N3 C17 85.1(4) . . . . ?
O4 Cu1 N3 C13 166.7(3) . . . . ?
O1 Cu1 N3 C13 74.5(4) . . . . ?
N2 Cu1 N3 C13 1.0(3) . . . . ?
Cl1 Cu1 N3 C13 -95.7(3) . . . . ?
O1 N1 C1 C2 180.0(4) . . . . ?
C6 N1 C1 C2 2.5(7) . . . . ?
N1 C1 C2 C4 -1.0(7) . . . . ?
N1 C1 C2 C3 177.5(4) . . . . ?
C1 C2 C3 O3 -171.5(5) . . . . ?
C4 C2 C3 O3 7.1(7) . . . . ?
C1 C2 C3 O2 8.5(7) . . . . ?
C4 C2 C3 O2 -172.9(4) . . . . ?
C1 C2 C4 C5 -1.6(7) . . . . ?
C3 C2 C4 C5 179.9(4) . . . . ?
C2 C4 C5 C6 2.8(7) . . . . ?
O1 N1 C6 C5 -178.6(4) . . . . ?
C1 N1 C6 C5 -1.3(6) . . . . ?
O1 N1 C6 C7 1.0(6) . . . . ?
C1 N1 C6 C7 178.3(4) . . . . ?
C4 C5 C6 N1 -1.4(7) . . . . ?
C4 C5 C6 C7 179.0(4) . . . . ?
Cu1 O4 C7 O5 174.9(4) . . . . ?
Cu1 O4 C7 C6 -8.6(7) . . . . ?
N1 C6 C7 O5 -160.7(4) . . . . ?
C5 C6 C7 O5 18.9(6) . . . . ?
N1 C6 C7 O4 22.6(7) . . . . ?
C5 C6 C7 O4 -157.8(4) . . . . ?
C12 N2 C8 C9 1.9(7) . . . . ?
Cu1 N2 C8 C9 -179.0(4) . . . . ?
N2 C8 C9 C10 -0.9(8) . . . . ?
C8 C9 C10 C11 -0.2(8) . . . . ?
C9 C10 C11 C12 0.2(8) . . . . ?
C8 N2 C12 C11 -1.9(7) . . . . ?
Cu1 N2 C12 C11 178.9(4) . . . . ?
C8 N2 C12 C13 -179.8(4) . . . . ?
Cu1 N2 C12 C13 1.1(5) . . . . ?
C10 C11 C12 N2 0.9(8) . . . . ?
C10 C11 C12 C13 178.5(5) . . . . ?
C17 N3 C13 C14 -1.0(7) . . . . ?
Cu1 N3 C13 C14 179.8(4) . . . . ?
C17 N3 C13 C12 178.5(4) . . . . ?
Cu1 N3 C13 C12 -0.7(5) . . . . ?
N2 C12 C13 N3 -0.2(6) . . . . ?
C11 C12 C13 N3 -178.0(4) . . . . ?
N2 C12 C13 C14 179.3(5) . . . . ?
C11 C12 C13 C14 1.5(8) . . . . ?
N3 C13 C14 C15 0.5(7) . . . . ?
C12 C13 C14 C15 -178.9(5) . . . . ?
C13 C14 C15 C16 0.4(8) . . . . ?
C14 C15 C16 C17 -0.7(8) . . . . ?
C13 N3 C17 C16 0.6(7) . . . . ?
Cu1 N3 C17 C16 179.8(4) . . . . ?
C15 C16 C17 N3 0.2(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        29.16
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.098
####################################################################### 
# 
# 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_khd259b
_database_code_depnum_ccdc_archive 'CCDC 1554224'
_audit_update_record             
;
2017-06-04 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H23 Cl Cu2 N6 O10, 2(H2 O)'
_chemical_formula_sum            'C34 H27 Cl Cu2 N6 O12'
_chemical_formula_weight         874.17

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7022(17)
_cell_length_b                   9.913(2)
_cell_length_c                   10.553(2)
_cell_angle_alpha                98.76(3)
_cell_angle_beta                 90.30(3)
_cell_angle_gamma                108.64(3)
_cell_volume                     851.1(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4556
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      29.14

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    1.404
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5706
_exptl_absorpt_correction_T_max  0.7665
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9424
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         29.14
_reflns_number_total             4556
_reflns_number_gt                3469
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0524P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4556
_refine_ls_number_parameters     256
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0975
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.978
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.49204(3) 0.21978(3) 0.40456(3) 0.03057(10) Uani 1 1 d . . .
Cl1 Cl 0.5000 0.0000 0.5000 0.0562(3) Uani 1 2 d S . .
O1 O 0.3806(2) 0.10999(18) 0.24318(16) 0.0364(4) Uani 1 1 d . . .
N3 N 0.5948(2) 0.3709(2) 0.55420(19) 0.0326(4) Uani 1 1 d . . .
N1 N 0.4375(2) 0.0049(2) 0.19046(18) 0.0291(4) Uani 1 1 d . . .
O4 O 0.6951(2) 0.25655(19) 0.32208(18) 0.0443(5) Uani 1 1 d . . .
N2 N 0.2908(2) 0.2379(2) 0.4852(2) 0.0330(4) Uani 1 1 d . . .
C1 C 0.3257(3) -0.1227(2) 0.1421(2) 0.0325(5) Uani 1 1 d . . .
H1 H 0.2159 -0.1336 0.1477 0.039 Uiso 1 1 calc R . .
C6 C 0.5994(3) 0.0251(3) 0.1831(2) 0.0335(5) Uani 1 1 d . . .
O3 O 0.2867(3) -0.4725(2) -0.0348(2) 0.0528(5) Uani 1 1 d . . .
O2 O 0.0985(2) -0.3886(2) 0.0585(2) 0.0523(5) Uani 1 1 d . . .
C8 C 0.1372(3) 0.1659(3) 0.4405(3) 0.0408(6) Uani 1 1 d . . .
H8 H 0.1184 0.1067 0.3608 0.049 Uiso 1 1 calc R . .
C3 C 0.2440(3) -0.3790(3) 0.0296(2) 0.0384(6) Uani 1 1 d . . .
O5 O 0.8591(3) 0.1913(3) 0.1866(2) 0.0762(8) Uani 1 1 d . . .
C2 C 0.3714(3) -0.2366(3) 0.0848(2) 0.0341(5) Uani 1 1 d . . .
C7 C 0.7273(3) 0.1701(3) 0.2340(2) 0.0403(6) Uani 1 1 d . . .
C12 C 0.3172(3) 0.3272(2) 0.5998(2) 0.0344(5) Uani 1 1 d . . .
C17 C 0.7558(3) 0.4372(3) 0.5780(3) 0.0398(6) Uani 1 1 d . . .
H17 H 0.8271 0.4121 0.5211 0.048 Uiso 1 1 calc R . .
C13 C 0.4915(3) 0.4068(2) 0.6361(2) 0.0339(5) Uani 1 1 d . . .
C15 C 0.7122(4) 0.5812(3) 0.7663(3) 0.0487(7) Uani 1 1 d . . .
H15 H 0.7518 0.6535 0.8369 0.058 Uiso 1 1 calc R . .
C11 C 0.1914(4) 0.3407(3) 0.6733(3) 0.0484(7) Uani 1 1 d . . .
H11 H 0.2120 0.4009 0.7524 0.058 Uiso 1 1 calc R . .
C16 C 0.8179(4) 0.5412(3) 0.6845(3) 0.0456(7) Uani 1 1 d . . .
H16 H 0.9295 0.5836 0.7006 0.055 Uiso 1 1 calc R . .
C5 C 0.6473(3) -0.0885(3) 0.1263(3) 0.0440(6) Uani 1 1 d . . .
H5 H 0.7575 -0.0761 0.1207 0.053 Uiso 1 1 calc R . .
C4 C 0.5353(3) -0.2198(3) 0.0779(3) 0.0425(6) Uani 1 1 d . . .
H4 H 0.5690 -0.2963 0.0410 0.051 Uiso 1 1 calc R . .
C14 C 0.5462(4) 0.5134(3) 0.7431(2) 0.0441(6) Uani 1 1 d . . .
H14 H 0.4731 0.5387 0.7980 0.053 Uiso 1 1 calc R . .
C9 C 0.0055(3) 0.1773(3) 0.5097(3) 0.0483(7) Uani 1 1 d . . .
H9 H -0.1000 0.1274 0.4765 0.058 Uiso 1 1 calc R . .
C10 C 0.0335(4) 0.2633(3) 0.6276(3) 0.0501(7) Uani 1 1 d . . .
H10 H -0.0531 0.2696 0.6767 0.060 Uiso 1 1 calc R . .
O6 O 0.0555(4) 0.1750(4) -0.0285(3) 0.0906(9) Uani 1 1 d D . .
H2 H 0.0000 -0.5000 0.0000 0.109 Uiso 1 2 d S . .
H6A H -0.009(5) 0.189(5) 0.035(4) 0.109 Uiso 1 1 d D . .
H6B H -0.004(6) 0.082(3) -0.024(5) 0.109 Uiso 1 1 d D . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O4 1.927(2) . ?
Cu1 O1 1.9414(17) . ?
Cu1 N3 1.986(2) . ?
Cu1 N2 1.999(2) . ?
Cu1 Cl1 2.5553(7) . ?
Cl1 Cu1 2.5553(7) 2_656 ?
O1 N1 1.341(2) . ?
N3 C13 1.342(3) . ?
N3 C17 1.347(3) . ?
N1 C1 1.348(3) . ?
N1 C6 1.363(3) . ?
O4 C7 1.261(3) . ?
N2 C8 1.341(3) . ?
N2 C12 1.357(3) . ?
C1 C2 1.371(3) . ?
C1 H1 0.9300 . ?
C6 C5 1.378(4) . ?
C6 C7 1.526(3) . ?
O3 C3 1.221(3) . ?
O2 C3 1.281(3) . ?
O2 H2 1.2318(18) . ?
C8 C9 1.387(4) . ?
C8 H8 0.9300 . ?
C3 C2 1.517(3) . ?
O5 C7 1.222(3) . ?
C2 C4 1.386(4) . ?
C12 C11 1.374(4) . ?
C12 C13 1.485(3) . ?
C17 C16 1.379(4) . ?
C17 H17 0.9300 . ?
C13 C14 1.388(3) . ?
C15 C16 1.373(4) . ?
C15 C14 1.388(4) . ?
C15 H15 0.9300 . ?
C11 C10 1.384(4) . ?
C11 H11 0.9300 . ?
C16 H16 0.9300 . ?
C5 C4 1.373(4) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C14 H14 0.9300 . ?
C9 C10 1.369(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
O6 H6A 0.901(19) . ?
O6 H6A 0.901(19) . ?
O6 H6B 0.909(19) . ?

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 Cu1 O1 89.07(8) . . ?
O4 Cu1 N3 91.47(9) . . ?
O1 Cu1 N3 166.23(7) . . ?
O4 Cu1 N2 164.24(8) . . ?
O1 Cu1 N2 94.76(8) . . ?
N3 Cu1 N2 81.22(9) . . ?
O4 Cu1 Cl1 97.94(7) . . ?
O1 Cu1 Cl1 95.26(6) . . ?
N3 Cu1 Cl1 98.29(6) . . ?
N2 Cu1 Cl1 96.92(6) . . ?
Cu1 Cl1 Cu1 180.0 . 2_656 ?
N1 O1 Cu1 114.74(13) . . ?
C13 N3 C17 119.3(2) . . ?
C13 N3 Cu1 115.37(16) . . ?
C17 N3 Cu1 125.34(18) . . ?
O1 N1 C1 116.49(19) . . ?
O1 N1 C6 122.40(18) . . ?
C1 N1 C6 121.1(2) . . ?
C7 O4 Cu1 124.94(16) . . ?
C8 N2 C12 118.7(2) . . ?
C8 N2 Cu1 126.55(18) . . ?
C12 N2 Cu1 114.62(17) . . ?
N1 C1 C2 121.0(2) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
N1 C6 C5 118.6(2) . . ?
N1 C6 C7 121.7(2) . . ?
C5 C6 C7 119.7(2) . . ?
C3 O2 H2 111.14(18) . . ?
N2 C8 C9 121.9(3) . . ?
N2 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
O3 C3 O2 126.3(2) . . ?
O3 C3 C2 119.1(2) . . ?
O2 C3 C2 114.7(2) . . ?
C1 C2 C4 119.1(2) . . ?
C1 C2 C3 120.4(2) . . ?
C4 C2 C3 120.5(2) . . ?
O5 C7 O4 124.5(2) . . ?
O5 C7 C6 115.4(2) . . ?
O4 C7 C6 120.1(2) . . ?
N2 C12 C11 121.7(2) . . ?
N2 C12 C13 113.9(2) . . ?
C11 C12 C13 124.4(2) . . ?
N3 C17 C16 121.9(3) . . ?
N3 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
N3 C13 C14 121.6(2) . . ?
N3 C13 C12 114.5(2) . . ?
C14 C13 C12 123.8(3) . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C15 C16 C17 118.9(3) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C4 C2 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C2 C4 H4 120.5 . . ?
C15 C14 C13 118.6(3) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
H6A O6 H6A 0(6) . . ?
H6A O6 H6B 80(4) . . ?
H6A O6 H6B 80(4) . . ?

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
O4 Cu1 Cl1 Cu1 71(100) . . . 2_656 ?
O1 Cu1 Cl1 Cu1 161(100) . . . 2_656 ?
N3 Cu1 Cl1 Cu1 -21(100) . . . 2_656 ?
N2 Cu1 Cl1 Cu1 -103(100) . . . 2_656 ?
O4 Cu1 O1 N1 53.57(16) . . . . ?
N3 Cu1 O1 N1 145.9(3) . . . . ?
N2 Cu1 O1 N1 -141.74(15) . . . . ?
Cl1 Cu1 O1 N1 -44.32(15) . . . . ?
O4 Cu1 N3 C13 168.87(17) . . . . ?
O1 Cu1 N3 C13 76.8(4) . . . . ?
N2 Cu1 N3 C13 2.90(16) . . . . ?
Cl1 Cu1 N3 C13 -92.89(16) . . . . ?
O4 Cu1 N3 C17 -11.1(2) . . . . ?
O1 Cu1 N3 C17 -103.2(4) . . . . ?
N2 Cu1 N3 C17 -177.1(2) . . . . ?
Cl1 Cu1 N3 C17 87.1(2) . . . . ?
Cu1 O1 N1 C1 136.61(17) . . . . ?
Cu1 O1 N1 C6 -44.7(3) . . . . ?
O1 Cu1 O4 C7 -33.5(2) . . . . ?
N3 Cu1 O4 C7 160.3(2) . . . . ?
N2 Cu1 O4 C7 -137.9(3) . . . . ?
Cl1 Cu1 O4 C7 61.7(2) . . . . ?
O4 Cu1 N2 C8 115.3(3) . . . . ?
O1 Cu1 N2 C8 11.7(2) . . . . ?
N3 Cu1 N2 C8 178.5(2) . . . . ?
Cl1 Cu1 N2 C8 -84.2(2) . . . . ?
O4 Cu1 N2 C12 -68.4(3) . . . . ?
O1 Cu1 N2 C12 -172.01(17) . . . . ?
N3 Cu1 N2 C12 -5.27(16) . . . . ?
Cl1 Cu1 N2 C12 92.09(16) . . . . ?
O1 N1 C1 C2 179.2(2) . . . . ?
C6 N1 C1 C2 0.5(4) . . . . ?
O1 N1 C6 C5 -179.4(2) . . . . ?
C1 N1 C6 C5 -0.8(4) . . . . ?
O1 N1 C6 C7 -0.4(3) . . . . ?
C1 N1 C6 C7 178.2(2) . . . . ?
C12 N2 C8 C9 -1.8(4) . . . . ?
Cu1 N2 C8 C9 174.3(2) . . . . ?
N1 C1 C2 C4 0.6(4) . . . . ?
N1 C1 C2 C3 -179.3(2) . . . . ?
O3 C3 C2 C1 170.9(3) . . . . ?
O2 C3 C2 C1 -10.1(4) . . . . ?
O3 C3 C2 C4 -9.0(4) . . . . ?
O2 C3 C2 C4 170.0(3) . . . . ?
Cu1 O4 C7 O5 -176.2(3) . . . . ?
Cu1 O4 C7 C6 1.3(4) . . . . ?
N1 C6 C7 O5 -156.7(3) . . . . ?
C5 C6 C7 O5 22.3(4) . . . . ?
N1 C6 C7 O4 25.6(4) . . . . ?
C5 C6 C7 O4 -155.4(3) . . . . ?
C8 N2 C12 C11 2.9(4) . . . . ?
Cu1 N2 C12 C11 -173.7(2) . . . . ?
C8 N2 C12 C13 -176.9(2) . . . . ?
Cu1 N2 C12 C13 6.5(3) . . . . ?
C13 N3 C17 C16 0.1(4) . . . . ?
Cu1 N3 C17 C16 -179.91(19) . . . . ?
C17 N3 C13 C14 1.7(4) . . . . ?
Cu1 N3 C13 C14 -178.36(19) . . . . ?
C17 N3 C13 C12 179.8(2) . . . . ?
Cu1 N3 C13 C12 -0.2(3) . . . . ?
N2 C12 C13 N3 -4.2(3) . . . . ?
C11 C12 C13 N3 176.1(2) . . . . ?
N2 C12 C13 C14 173.9(2) . . . . ?
C11 C12 C13 C14 -5.8(4) . . . . ?
N2 C12 C11 C10 -1.3(4) . . . . ?
C13 C12 C11 C10 178.4(2) . . . . ?
C14 C15 C16 C17 2.2(4) . . . . ?
N3 C17 C16 C15 -2.0(4) . . . . ?
N1 C6 C5 C4 0.0(4) . . . . ?
C7 C6 C5 C4 -179.1(3) . . . . ?
C6 C5 C4 C2 1.0(4) . . . . ?
C1 C2 C4 C5 -1.3(4) . . . . ?
C3 C2 C4 C5 178.6(2) . . . . ?
C16 C15 C14 C13 -0.5(4) . . . . ?
N3 C13 C14 C15 -1.4(4) . . . . ?
C12 C13 C14 C15 -179.4(2) . . . . ?
N2 C8 C9 C10 -0.8(4) . . . . ?
C8 C9 C10 C11 2.3(4) . . . . ?
C12 C11 C10 C9 -1.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        29.14
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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 1554217'
_audit_update_record             
;
2017-06-04 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;

_audit_creation_date             2015-03-04T16:25:59-00:00
_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            'C14 H26 Co2 N2 O20'
_chemical_formula_weight         660.23

#----------------------------------------------------------------------------#
#                   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                   12.9792(19)
_cell_length_b                   9.746(3)
_cell_length_c                   19.835(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.290(14)
_cell_angle_gamma                90
_cell_volume                     2420.2(10)
_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_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.469
_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_orient_matrix_ub_11      0.019555
_diffrn_orient_matrix_ub_12      -0.014859
_diffrn_orient_matrix_ub_13      -0.04496
_diffrn_orient_matrix_ub_21      0.061093
_diffrn_orient_matrix_ub_22      -0.05939
_diffrn_orient_matrix_ub_23      0.02479
_diffrn_orient_matrix_ub_31      -0.047593
_diffrn_orient_matrix_ub_32      -0.082347
_diffrn_orient_matrix_ub_33      -0.009782
_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
0 0 0
0 0 0
0 0 0
0 0 0
4 -2 1

_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_number            1471
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.129
_diffrn_reflns_theta_max         24.963
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.639
_diffrn_measured_fraction_theta_max 0.661
_diffrn_reflns_Laue_measured_fraction_full 0.639
_diffrn_reflns_Laue_measured_fraction_max 0.661
_diffrn_reflns_point_group_measured_fraction_full 0.639
_diffrn_reflns_point_group_measured_fraction_max 0.661
_reflns_number_total             1403
_reflns_number_gt                1147
_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   difmap

#----------------------------------------------------------------------------#
#                   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)+(0.0783P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1403
_refine_ls_number_parameters     226
_refine_ls_number_restraints     9
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.084

#----------------------------------------------------------------------------#
#                   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'
Co Co 0.3494 0.9721 '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
Co1 Co 0.25 0.25 0 0.0267(5) Uani 1 d . .
Co2 Co 0.5 0.11425(9) 0.25 0.0320(7) Uani 1 d . .
O1 O 0.2753(3) 0.0819(3) 0.0629(2) 0.0393(13) Uani 1 d . .
O2 O 0.2321(3) -0.1141(4) 0.1023(2) 0.0423(15) Uani 1 d . .
O3 O 0.0983(2) 0.1821(3) -0.0352(2) 0.0304(12) Uani 1 d . .
O4 O -0.1302(3) -0.0465(4) -0.2454(2) 0.0366(13) Uani 1 d . .
O5 O -0.1631(3) -0.2445(3) -0.1989(2) 0.0323(13) Uani 1 d . .
O6 O 0.3020(4) 0.1373(5) -0.0761(3) 0.0446(18) Uani 1 d . .
O7 O 0.6155(3) 0.2701(4) 0.2715(3) 0.0479(17) Uani 1 d . .
O8 O 0.4946(3) 0.0992(4) 0.3539(3) 0.0367(15) Uani 1 d . .
O9 O 0.6237(3) -0.0284(4) 0.2737(3) 0.0415(15) Uani 1 d . .
O10 O 0.2875(3) 0.1172(4) 0.3643(3) 0.0349(15) Uani 1 d . .
C1 C 0.1354(3) -0.0528(5) -0.0105(3) 0.0210(16) Uani 1 d . .
N2 N 0.0825(3) 0.0499(4) -0.0530(2) 0.0217(13) Uani 1 d . .
C3 C 0.0082(3) 0.0224(5) -0.1135(3) 0.0238(17) Uani 1 d . .
C4 C -0.0205(3) -0.1103(4) -0.1336(3) 0.0216(18) Uani 1 d . .
C5 C 0.0316(4) -0.2168(5) -0.0923(4) 0.0289(19) Uani 1 d . .
C6 C 0.1082(4) -0.1873(5) -0.0316(4) 0.0274(18) Uani 1 d . .
C7 C 0.2194(4) -0.0240(5) 0.0567(3) 0.0269(18) Uani 1 d . .
C8 C -0.1109(4) -0.1347(5) -0.1990(4) 0.030(2) Uani 1 d . .
H1 H 0.241(5) 0.108(6) 0.323(4) 0.05(2) Uiso 1 d . .
H2 H 0.281(6) 0.208(9) 0.380(4) 0.10(3) Uiso 1 d . .
H3 H -0.024(3) 0.105(4) -0.139(3) 0.022(13) Uiso 1 d . .
H5 H 0.011(4) -0.314(6) -0.106(3) 0.043(16) Uiso 1 d . .
H6 H 0.147(4) -0.253(5) 0.000(3) 0.035(16) Uiso 1 d . .
H61 H 0.287(5) 0.053(7) -0.088(4) 0.08(2) Uiso 1 d . .
H62 H 0.313(5) 0.182(7) -0.106(4) 0.04(2) Uiso 1 d . .
H71 H 0.600(5) 0.350(7) 0.261(4) 0.07(2) Uiso 1 d . .
H72 H 0.669(5) 0.251(6) 0.276(4) 0.05(2) Uiso 1 d . .
H81 H 0.544(6) 0.137(12) 0.390(4) 0.23(6) Uiso 1 d . .
H82 H 0.435(4) 0.084(9) 0.369(5) 0.15(4) Uiso 1 d . .
H91 H 0.672(5) -0.040(6) 0.315(4) 0.06(2) Uiso 1 d . .
H92 H 0.636(5) -0.085(7) 0.249(4) 0.06(3) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   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 O3 2.018(3) 7 ?
Co1 O3 2.018(3) . ?
Co1 O1 2.032(4) 7 ?
Co1 O1 2.032(4) . ?
Co1 O6 2.116(6) . ?
Co1 O6 2.116(6) 7 ?
Co2 O9 2.081(4) . ?
Co2 O9 2.081(4) 2_655 ?
Co2 O8 2.086(6) 2_655 ?
Co2 O8 2.086(6) . ?
Co2 O7 2.097(4) 2_655 ?
Co2 O7 2.097(4) . ?
O1 C7 1.249(6) . ?
O2 C7 1.241(7) . ?
O3 N2 1.338(5) . ?
O4 C8 1.235(7) . ?
O5 C8 1.267(6) . ?
C1 N2 1.371(6) . ?
C1 C6 1.393(7) . ?
C1 C7 1.509(7) . ?
N2 C3 1.353(7) . ?
C3 C4 1.376(6) . ?
C4 C5 1.384(7) . ?
C4 C8 1.520(8) . ?
C5 C6 1.374(8) . ?

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 Co1 O3 180 7 . ?
O3 Co1 O1 86.17(14) 7 7 ?
O3 Co1 O1 93.83(14) . 7 ?
O3 Co1 O1 93.83(14) 7 . ?
O3 Co1 O1 86.17(14) . . ?
O1 Co1 O1 180 7 . ?
O3 Co1 O6 87.23(16) 7 . ?
O3 Co1 O6 92.77(16) . . ?
O1 Co1 O6 90.6(2) 7 . ?
O1 Co1 O6 89.4(2) . . ?
O3 Co1 O6 92.77(16) 7 7 ?
O3 Co1 O6 87.23(16) . 7 ?
O1 Co1 O6 89.4(2) 7 7 ?
O1 Co1 O6 90.6(2) . 7 ?
O6 Co1 O6 180 . 7 ?
O9 Co2 O9 96.2(3) . 2_655 ?
O9 Co2 O8 87.2(2) . 2_655 ?
O9 Co2 O8 87.4(2) 2_655 2_655 ?
O9 Co2 O8 87.4(2) . . ?
O9 Co2 O8 87.2(2) 2_655 . ?
O8 Co2 O8 171.9(2) 2_655 . ?
O9 Co2 O7 175.47(18) . 2_655 ?
O9 Co2 O7 88.32(18) 2_655 2_655 ?
O8 Co2 O7 93.3(2) 2_655 2_655 ?
O8 Co2 O7 92.50(19) . 2_655 ?
O9 Co2 O7 88.32(18) . . ?
O9 Co2 O7 175.47(18) 2_655 . ?
O8 Co2 O7 92.5(2) 2_655 . ?
O8 Co2 O7 93.3(2) . . ?
O7 Co2 O7 87.2(2) 2_655 . ?
C7 O1 Co1 127.6(4) . . ?
N2 O3 Co1 118.4(2) . . ?
N2 C1 C6 117.1(5) . . ?
N2 C1 C7 122.4(4) . . ?
C6 C1 C7 120.5(4) . . ?
O3 N2 C3 116.7(4) . . ?
O3 N2 C1 121.6(4) . . ?
C3 N2 C1 121.7(4) . . ?
N2 C3 C4 121.2(5) . . ?
C3 C4 C5 118.7(5) . . ?
C3 C4 C8 118.9(5) . . ?
C5 C4 C8 122.4(4) . . ?
C6 C5 C4 119.4(5) . . ?
C5 C6 C1 121.8(5) . . ?
O2 C7 O1 123.4(5) . . ?
O2 C7 C1 116.0(4) . . ?
O1 C7 C1 120.4(5) . . ?
O4 C8 O5 125.7(5) . . ?
O4 C8 C4 119.1(4) . . ?
O5 C8 C4 115.1(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
Co1 O3 N2 C3 -135.5(4) . . . . ?
Co1 O3 N2 C1 47.5(6) . . . . ?
C6 C1 N2 O3 175.9(4) . . . . ?
C7 C1 N2 O3 -3.8(7) . . . . ?
C6 C1 N2 C3 -1.0(8) . . . . ?
C7 C1 N2 C3 179.3(5) . . . . ?
O3 N2 C3 C4 -174.6(5) . . . . ?
C1 N2 C3 C4 2.5(8) . . . . ?
N2 C3 C4 C5 -2.8(9) . . . . ?
N2 C3 C4 C8 175.0(5) . . . . ?
C3 C4 C5 C6 1.7(9) . . . . ?
C8 C4 C5 C6 -176.0(5) . . . . ?
C4 C5 C6 C1 -0.3(9) . . . . ?
N2 C1 C6 C5 -0.1(8) . . . . ?
C7 C1 C6 C5 179.7(5) . . . . ?
Co1 O1 C7 O2 -169.9(4) . . . . ?
Co1 O1 C7 C1 14.0(7) . . . . ?
N2 C1 C7 O2 153.5(5) . . . . ?
C6 C1 C7 O2 -26.2(8) . . . . ?
N2 C1 C7 O1 -30.0(8) . . . . ?
C6 C1 C7 O1 150.2(5) . . . . ?
C3 C4 C8 O4 26.3(8) . . . . ?
C5 C4 C8 O4 -156.0(6) . . . . ?
C3 C4 C8 O5 -150.9(5) . . . . ?
C5 C4 C8 O5 26.8(8) . . . . ?

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
O10 H1 O4 0.89(7) 1.90(7) 2.769(6) 165(6) 5
O10 H2 O2 0.95(9) 1.79(9) 2.729(5) 173(8) 4
O6 H61 O10 0.86(7) 1.91(7) 2.733(6) 158(7) 6
O6 H62 O5 0.78(7) 2.07(7) 2.837(8) 166(8) 3
O7 H71 O4 0.81(7) 2.00(7) 2.759(6) 155(6) 7
O7 H72 O5 0.70(7) 2.10(7) 2.788(5) 166(7) 6_656
O8 H81 O1 0.91(2) 2.35(8) 3.012(5) 130(9) 2_655
O8 H81 O3 0.91(2) 2.29(6) 3.103(6) 149(10) 8_556
O8 H82 O10 0.91(2) 1.92(5) 2.755(6) 152(9) .
O9 H91 O1 0.90(7) 2.62(7) 3.338(7) 137(5) 2_655
O9 H91 O2 0.90(7) 1.92(7) 2.796(6) 165(6) 2_655
O9 H92 O5 0.78(7) 2.02(7) 2.786(6) 169(8) 7_545

####################################################################### 
# 
# 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_khd260b
_database_code_depnum_ccdc_archive 'CCDC 1554225'
_audit_update_record             
;
2017-06-04 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
_space_group_name_Hall           '-P 1'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
_cell_length_a                   9.0136(18)
_cell_length_b                   10.366(2)
_cell_length_c                   12.609(3)
_cell_angle_alpha                113.63(3)
_cell_angle_beta                 91.47(3)
_cell_angle_gamma                106.35(3)
_cell_volume                     1022.76
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
Ag1 Ag 0.00167(5) 0.92648(4) 0.37588(3)
Cu1 Cu 0.38316(6) 0.24339(5) 0.32465(5)
O1 O 0.3829(4) 0.4467(3) 0.3879(3)
O2 O 0.3222(4) 0.2193(3) 0.4610(3)
O3 O 0.2470(4) 0.2836(4) 0.6346(3)
O4 O 0.1608(4) 0.8393(4) 0.4548(3)
O5 O 0.0553(4) 0.8749(3) 0.6184(3)
O6 O 0.1442(4) 0.1483(4) 0.2186(4)
O7 O 0.0461(8) 0.7680(6) 0.1916(5)
N1 N 0.2944(4) 0.4983(3) 0.4679(3)
N2 N 0.4641(4) 0.0704(4) 0.2797(3)
N3 N 0.4989(4) 0.2760(4) 0.2000(3)
C1 C 0.2571(4) 0.6158(4) 0.4668(4)
H1 H 0.2880 0.6492 0.4100
C2 C 0.1734(4) 0.6870(4) 0.5493(3)
C3 C 0.1268(4) 0.8115(4) 0.5394(4)
C4 C 0.1275(4) 0.6339(4) 0.6320(4)
H4 H 0.0729 0.6804 0.6889
C5 C 0.1626(4) 0.5122(4) 0.6298(4)
H5 H 0.1300 0.4761 0.6848
C6 C 0.2460(4) 0.4426(4) 0.5468(4)
C7 C 0.2766(5) 0.3049(5) 0.5475(4)
C8 C 0.4470(6) -0.0278(5) 0.3246(5)
H8 H 0.3806 -0.0265 0.3801
C9 C 0.5249(6) -0.1324(6) 0.2917(6)
H9 H 0.5104 -0.1998 0.3248
C10 C 0.6227(6) -0.1365(5) 0.2105(5)
H10 H 0.6767 -0.2052 0.1892
C11 C 0.6413(5) -0.0370(5) 0.1596(4)
C12 C 0.5594(4) 0.0663(4) 0.1983(4)
C13 C 0.7416(5) -0.0279(6) 0.0732(5)
H13 H 0.7969 -0.0952 0.0461
C14 C 0.7576(5) 0.0735(6) 0.0311(4)
H14 H 0.8225 0.0743 -0.0250
C15 C 0.6761(5) 0.1827(5) 0.0707(4)
C16 C 0.5781(5) 0.1774(4) 0.1546(4)
C17 C 0.5160(5) 0.3828(5) 0.1642(4)
H17 H 0.4631 0.4514 0.1953
C18 C 0.6112(6) 0.3946(6) 0.0813(5)
H18 H 0.6204 0.4700 0.0573
C19 C 0.6916(6) 0.2956(6) 0.0349(4)
H19 H 0.7559 0.3039 -0.0202
H6A H 0.123(7) 0.200(7) 0.196(6)
H7A H -0.033(6) 0.745(8) 0.138(5)
H6B H 0.083(7) 0.135(7) 0.259(6)
H7B H 0.043(8) 0.681(4) 0.185(7)
Ag1 Ag -0.00167(5) 0.07352(4) 0.62412(3)
Ag1 Ag -0.00167(5) 1.07352(4) 0.62412(3)
O3 O -0.2470(4) 0.7164(4) 0.3654(3)
O5 O -0.0553(4) 1.1251(3) 0.3816(3)
O8 O 0.1425(15) 0.3170(12) 0.0496(10)
O9 O 0.0962(12) 0.436(2) 0.1939(10)
O10 O 0.180(3) 0.521(2) 0.104(3)
N4 N 0.1343(7) 0.4227(5) 0.1129(5)
####################################################################### 
# 
# 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_khc1023-2h
_database_code_depnum_ccdc_archive 'CCDC 1568348'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;
_audit_creation_date             2017-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 Co N3 O7, 5.11(H2 O), 0.19(C2 H6 O)'
_chemical_formula_sum            'C19.36 H26.35 Co N3 O12.32'
_chemical_formula_weight         557.07
_chemical_melting_point          ?
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'
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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9216(16)
_cell_length_b                   9.862(2)
_cell_length_c                   16.736(3)
_cell_angle_alpha                91.96(3)
_cell_angle_beta                 102.07(3)
_cell_angle_gamma                108.51(3)
_cell_volume                     1205.3(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.720
_shelx_estimated_absorpt_T_min   0.696
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             578
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.45
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13150
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.177
_diffrn_reflns_theta_min         2.504
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5315
_reflns_number_total             6451
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         6451
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+0.8121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1200
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O13-H13A = O13-H13B = O13A-H13C = O13A-H13D
 0.95 with sigma of 0.02
 O10-H10A = O10-H10B = O11-H11A = O11-H11B = O12-H12A = O12-H12B
 0.95 with sigma of 0.02
 H13A-H13B = H13C-H13D = H10A-H10B = H11A-H11B = H12A-H12B
 1.41 with sigma of 0.02
 H8A-H11A
 -2.22 with sigma of 0.001
 O14-C22
 1.4 with sigma of 0.001
 C22-C23
 1.45 with sigma of 0.001
 O14-C23
 2.45 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C22) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(O8) = Uanis(O14)
Uanis(O9) = Uanis(C23)
4. Others
 1*[Sof(O8)+Sof(H8A)+Sof(H8B)+Sof(O14)+Sof(H14A)+Sof(C22)+Sof(H22A)+Sof(H22B)+
 Sof(C23)+Sof(H23A)+Sof(H23B)+Sof(H23C)]+1*[Sof(O9)+Sof(H9A)+Sof(H9B)]=0.5 with
 esd of 0.0001
 Sof(O13A)=Sof(H13C)=Sof(H13D)=1-FVAR(1)
 Sof(O13)=Sof(H13A)=Sof(H13B)=FVAR(1)
 Sof(O8)=Sof(H8A)=Sof(H8B)=1-FVAR(2)
 Sof(O14)=Sof(H14A)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=
 Sof(H23C)=FVAR(2)
 Sof(O9)=Sof(H9A)=Sof(H9B)=FVAR(3)
 Fixed X: H9A(-0.0472) H9B(-0.10887)
 Fixed Y: H9A(0.60976) H9B(0.52478)
 Fixed Z: H9A(0.04272) H9B(-0.02404)
5.a Free rotating group:
 O8(H8A,H8B)
5.b Rotating group:
 O6(H6A,H6B)
5.c Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19)
5.e Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
5.f Idealised tetrahedral OH refined as rotating group:
 O14(H14A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Co1 Co 0.25482(4) 0.18925(3) 0.30145(2) 0.01199(9) Uani 1 1 d . . . . .
O1 O 0.0234(2) 0.02084(17) 0.23746(9) 0.0161(3) Uani 1 1 d . . . . .
O2 O -0.2564(2) -0.1542(2) -0.05345(10) 0.0235(4) Uani 1 1 d . . . . .
O3 O -0.3191(2) 0.0333(2) -0.10685(10) 0.0238(4) Uani 1 1 d . . . . .
O4 O 0.0656(2) 0.27770(19) 0.32593(10) 0.0190(3) Uani 1 1 d . . . . .
O5 O -0.2249(2) 0.2652(2) 0.30860(10) 0.0219(4) Uani 1 1 d . . . . .
O6 O 0.2728(2) 0.30081(18) 0.19628(9) 0.0189(3) Uani 1 1 d . . . . .
H6A H 0.248185 0.239446 0.152315 0.028 Uiso 1 1 d GR . . . .
H6B H 0.384441 0.363140 0.202063 0.028 Uiso 1 1 d GR . . . .
O7 O 0.4231(2) 0.08791(19) 0.26412(10) 0.0165(3) Uani 1 1 d . . . . .
H7A H 0.384(5) 0.051(4) 0.215(3) 0.043(10) Uiso 1 1 d . . . . .
H7B H 0.529(6) 0.149(5) 0.273(2) 0.047(11) Uiso 1 1 d . . . . .
N1 N -0.0830(2) 0.0655(2) 0.17867(11) 0.0141(3) Uani 1 1 d . . . . .
N2 N 0.2680(2) 0.0963(2) 0.41485(11) 0.0143(3) Uani 1 1 d . . . . .
N3 N 0.4805(2) 0.3491(2) 0.37965(11) 0.0140(3) Uani 1 1 d . . . . .
C1 C -0.1272(3) -0.0021(2) 0.10176(13) 0.0152(4) Uani 1 1 d . . . . .
H1 H -0.087928 -0.081288 0.091628 0.018 Uiso 1 1 calc R . . . .
C2 C -0.2298(3) 0.0439(3) 0.03778(13) 0.0168(4) Uani 1 1 d . . . . .
C3 C -0.2720(3) -0.0317(3) -0.04840(13) 0.0176(4) Uani 1 1 d . . . . .
C4 C -0.2889(3) 0.1578(3) 0.05366(14) 0.0200(4) Uani 1 1 d . . . . .
H4 H -0.355101 0.193224 0.010057 0.024 Uiso 1 1 calc R . . . .
C5 C -0.2505(3) 0.2199(3) 0.13411(13) 0.0187(4) Uani 1 1 d . . . . .
H5 H -0.296052 0.294611 0.146067 0.022 Uiso 1 1 calc R . . . .
C6 C -0.1452(3) 0.1727(2) 0.19713(13) 0.0148(4) Uani 1 1 d . . . . .
C7 C -0.0969(3) 0.2427(2) 0.28513(12) 0.0140(4) Uani 1 1 d . . . . .
C8 C 0.1597(3) -0.0261(3) 0.43209(14) 0.0189(4) Uani 1 1 d . . . . .
H8 H 0.061636 -0.084671 0.389386 0.023 Uiso 1 1 calc R . . . .
C9 C 0.1825(3) -0.0738(3) 0.51018(15) 0.0204(4) Uani 1 1 d . . . . .
H9 H 0.101285 -0.162457 0.519984 0.025 Uiso 1 1 calc R . . . .
C10 C 0.3244(3) 0.0098(3) 0.57258(14) 0.0202(4) Uani 1 1 d . . . . .
H10 H 0.341717 -0.020443 0.626086 0.024 Uiso 1 1 calc R . . . .
C11 C 0.4428(3) 0.1397(2) 0.55655(13) 0.0165(4) Uani 1 1 d . . . . .
C12 C 0.4080(3) 0.1795(2) 0.47642(12) 0.0133(4) Uani 1 1 d . . . . .
C13 C 0.5957(3) 0.2332(3) 0.61781(13) 0.0201(4) Uani 1 1 d . . . . .
H13 H 0.619226 0.207100 0.672099 0.024 Uiso 1 1 calc R . . . .
C14 C 0.7057(3) 0.3572(3) 0.59921(14) 0.0212(5) Uani 1 1 d . . . . .
H14 H 0.806910 0.416279 0.640406 0.025 Uiso 1 1 calc R . . . .
C15 C 0.6728(3) 0.4017(2) 0.51818(13) 0.0169(4) Uani 1 1 d . . . . .
C16 C 0.5238(3) 0.3128(2) 0.45704(12) 0.0134(4) Uani 1 1 d . . . . .
C17 C 0.7815(3) 0.5313(3) 0.49591(14) 0.0214(5) Uani 1 1 d . . . . .
H17 H 0.884924 0.593736 0.534743 0.026 Uiso 1 1 calc R . . . .
C18 C 0.7365(3) 0.5665(3) 0.41760(15) 0.0227(5) Uani 1 1 d . . . . .
H18 H 0.807341 0.654264 0.401823 0.027 Uiso 1 1 calc R . . . .
C19 C 0.5849(3) 0.4717(3) 0.36110(14) 0.0187(4) Uani 1 1 d . . . . .
H19 H 0.555882 0.496859 0.306874 0.022 Uiso 1 1 calc R . . . .
O8 O 0.1478(5) 0.5199(6) 0.1604(3) 0.0388(8) Uani 0.807(3) 1 d . . P A 1
H8A H 0.156503 0.508332 0.212290 0.058 Uiso 0.807(3) 1 d DG . P A 1
H8B H 0.226749 0.602095 0.155580 0.058 Uiso 0.807(3) 1 d G . P A 1
O9 O -0.0999(16) 0.5092(13) 0.0171(7) 0.068(3) Uani 0.307(3) 1 d . . P A 1
H9A H -0.047200 0.609760 0.042720 0.102 Uiso 0.307(3) 1 d R . P A 1
H9B H -0.108870 0.524780 -0.024040 0.102 Uiso 0.307(3) 1 d R . P A 1
O14 O 0.111(3) 0.532(3) 0.1558(9) 0.0388(8) Uani 0.193(3) 1 d D . P A -1
H14A H 0.225275 0.557889 0.169603 0.058 Uiso 0.193(3) 1 calc GR . P A -1
C22 C 0.053(3) 0.506(2) 0.0700(9) 0.070(6) Uani 0.193(3) 1 d D U P A -1
H22A H -0.013053 0.401322 0.055692 0.084 Uiso 0.193(3) 1 calc R . P A -1
H22B H 0.163808 0.528848 0.047543 0.084 Uiso 0.193(3) 1 calc R . P A -1
C23 C -0.063(3) 0.581(2) 0.0275(11) 0.068(3) Uani 0.193(3) 1 d D . P A -1
H23A H -0.010471 0.683924 0.047517 0.102 Uiso 0.193(3) 1 calc GR . P A -1
H23B H -0.185504 0.542283 0.037875 0.102 Uiso 0.193(3) 1 calc GR . P A -1
H23C H -0.070870 0.568896 -0.031703 0.102 Uiso 0.193(3) 1 calc GR . P A -1
O10 O 0.5987(4) 0.6340(3) 0.04119(18) 0.0518(6) Uani 1 1 d D . . . .
H10A H 0.658(5) 0.712(4) 0.012(3) 0.078 Uiso 1 1 d DR . . . .
H10B H 0.484(3) 0.617(4) 0.0045(16) 0.078 Uiso 1 1 d DR . . . .
O11 O 0.4528(3) 0.7472(2) 0.15629(13) 0.0334(4) Uani 1 1 d D . . . .
H11A H 0.410(5) 0.818(3) 0.137(2) 0.050 Uiso 1 1 d DR . . . .
H11B H 0.504(4) 0.723(4) 0.1176(13) 0.050 Uiso 1 1 d DR . . . .
O12 O 0.7766(3) 0.7752(2) 0.27145(14) 0.0376(5) Uani 1 1 d D . . . .
H12A H 0.862(4) 0.861(3) 0.261(2) 0.056 Uiso 1 1 d DR . . . .
H12B H 0.671(3) 0.779(4) 0.2366(18) 0.056 Uiso 1 1 d DR . . . .
O13 O 0.8927(6) 0.5483(5) 0.2442(3) 0.0405(13) Uani 0.542(7) 1 d D . P B 1
H13A H 0.861(11) 0.634(5) 0.238(5) 0.061 Uiso 0.542(7) 1 d DR . P B 1
H13B H 0.838(10) 0.518(7) 0.288(3) 0.061 Uiso 0.542(7) 1 d DR . P B 1
O13A O 0.8399(8) 0.5720(6) 0.1759(4) 0.0453(17) Uani 0.458(7) 1 d D . P B 2
H13C H 0.903(12) 0.663(5) 0.210(5) 0.068 Uiso 0.458(7) 1 d DR . P B 2
H13D H 0.769(11) 0.608(9) 0.136(4) 0.068 Uiso 0.458(7) 1 d DR . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.0952(18) . ?
Co1 O4 2.0585(17) . ?
Co1 O6 2.1133(17) . ?
Co1 O7 2.0778(17) . ?
Co1 N2 2.1327(19) . ?
Co1 N3 2.118(2) . ?
O1 N1 1.338(2) . ?
O2 C3 1.255(3) . ?
O3 C3 1.245(3) . ?
O4 C7 1.256(2) . ?
O5 C7 1.239(3) . ?
O6 H6A 0.8834 . ?
O6 H6B 0.8854 . ?
O7 H7A 0.84(4) . ?
O7 H7B 0.84(4) . ?
N1 C1 1.352(3) . ?
N1 C6 1.352(3) . ?
N2 C8 1.322(3) . ?
N2 C12 1.361(3) . ?
N3 C16 1.359(3) . ?
N3 C19 1.319(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.384(3) . ?
C2 C3 1.521(3) . ?
C2 C4 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(3) . ?
C6 C7 1.523(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.399(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.400(3) . ?
C11 C12 1.407(3) . ?
C11 C13 1.440(3) . ?
C12 C16 1.436(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.347(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.437(3) . ?
C15 C16 1.409(3) . ?
C15 C17 1.408(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.371(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.401(3) . ?
C19 H19 0.9500 . ?
O8 H8A 0.8708 . ?
O8 H8B 0.8707 . ?
O8 C22 1.522(17) . ?
O9 H9A 0.987(12) . ?
O9 H9B 0.704(12) . ?
O9 C22 1.35(2) . ?
O9 C23 0.68(2) . ?
O14 H14A 0.8400 . ?
O14 C22 1.4002(11) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.4499(11) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O10 H10A 0.968(19) . ?
O10 H10B 0.948(18) . ?
O11 H11A 0.910(18) . ?
O11 H11B 0.895(17) . ?
O12 H12A 0.948(18) . ?
O12 H12B 0.924(17) . ?
O13 H13A 0.95(2) . ?
O13 H13B 0.94(2) . ?
O13A H13C 0.97(2) . ?
O13A H13D 0.94(2) . ?

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 Co1 O6 92.47(7) . . ?
O1 Co1 N2 94.57(7) . . ?
O1 Co1 N3 172.87(7) . . ?
O4 Co1 O1 83.97(7) . . ?
O4 Co1 O6 90.24(7) . . ?
O4 Co1 O7 173.25(6) . . ?
O4 Co1 N2 91.33(7) . . ?
O4 Co1 N3 94.17(7) . . ?
O6 Co1 N2 172.91(7) . . ?
O6 Co1 N3 94.42(7) . . ?
O7 Co1 O1 90.07(7) . . ?
O7 Co1 O6 86.84(7) . . ?
O7 Co1 N2 92.31(7) . . ?
O7 Co1 N3 92.12(7) . . ?
N3 Co1 N2 78.57(8) . . ?
N1 O1 Co1 112.52(13) . . ?
C7 O4 Co1 124.46(14) . . ?
Co1 O6 H6A 110.0 . . ?
Co1 O6 H6B 110.4 . . ?
H6A O6 H6B 108.7 . . ?
Co1 O7 H7A 112(3) . . ?
Co1 O7 H7B 107(3) . . ?
H7A O7 H7B 113(4) . . ?
O1 N1 C1 117.56(18) . . ?
O1 N1 C6 120.30(17) . . ?
C1 N1 C6 122.13(18) . . ?
C8 N2 Co1 129.05(15) . . ?
C8 N2 C12 117.98(19) . . ?
C12 N2 Co1 112.96(15) . . ?
C16 N3 Co1 113.42(14) . . ?
C19 N3 Co1 128.28(15) . . ?
C19 N3 C16 118.21(18) . . ?
N1 C1 H1 120.0 . . ?
N1 C1 C2 120.1(2) . . ?
C2 C1 H1 120.0 . . ?
C1 C2 C3 118.7(2) . . ?
C1 C2 C4 119.4(2) . . ?
C4 C2 C3 122.0(2) . . ?
O2 C3 C2 116.5(2) . . ?
O3 C3 O2 126.4(2) . . ?
O3 C3 C2 117.1(2) . . ?
C2 C4 H4 120.4 . . ?
C2 C4 C5 119.3(2) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.1(2) . . ?
C6 C5 H5 120.0 . . ?
N1 C6 C5 118.9(2) . . ?
N1 C6 C7 120.42(18) . . ?
C5 C6 C7 120.7(2) . . ?
O4 C7 C6 119.01(19) . . ?
O5 C7 O4 125.85(19) . . ?
O5 C7 C6 115.07(17) . . ?
N2 C8 H8 118.4 . . ?
N2 C8 C9 123.2(2) . . ?
C9 C8 H8 118.4 . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.0(2) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.5(2) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 117.5(2) . . ?
C10 C11 C13 123.3(2) . . ?
C12 C11 C13 119.3(2) . . ?
N2 C12 C11 122.9(2) . . ?
N2 C12 C16 117.43(18) . . ?
C11 C12 C16 119.72(19) . . ?
C11 C13 H13 119.5 . . ?
C14 C13 C11 120.9(2) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 119.2(2) . . ?
C17 C15 C14 123.5(2) . . ?
C17 C15 C16 117.3(2) . . ?
N3 C16 C12 117.51(18) . . ?
N3 C16 C15 122.8(2) . . ?
C15 C16 C12 119.71(19) . . ?
C15 C17 H17 120.3 . . ?
C18 C17 C15 119.3(2) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.3(2) . . ?
C19 C18 H18 120.4 . . ?
N3 C19 C18 123.1(2) . . ?
N3 C19 H19 118.4 . . ?
C18 C19 H19 118.4 . . ?
H8A O8 H8B 109.4 . . ?
C22 O8 H8A 156.7 . . ?
C22 O8 H8B 90.6 . . ?
H9A O9 H9B 96.9(13) . . ?
C22 O9 H9A 78.8(10) . . ?
C22 O9 H9B 127.3(17) . . ?
C23 O9 H9A 10.7(19) . . ?
C23 O9 H9B 86(2) . . ?
C23 O9 C22 84.0(18) . . ?
C22 O14 H14A 109.5 . . ?
O8 C22 H22A 104.3 . . ?
O8 C22 H22B 97.6 . . ?
O9 C22 O8 144.3(15) . . ?
O9 C22 O14 131.9(15) . . ?
O9 C22 H22A 80.1 . . ?
O9 C22 H22B 115.2 . . ?
O9 C22 C23 27.7(10) . . ?
O14 C22 O8 12.7(8) . . ?
O14 C22 H22A 107.7 . . ?
O14 C22 H22B 107.7 . . ?
O14 C22 C23 118.53(13) . . ?
H22A C22 H22B 107.1 . . ?
C23 C22 O8 130.4(9) . . ?
C23 C22 H22A 107.7 . . ?
C23 C22 H22B 107.7 . . ?
O9 C23 C22 68.2(17) . . ?
O9 C23 H23A 174.9 . . ?
O9 C23 H23B 67.8 . . ?
O9 C23 H23C 75.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H10A O10 H10B 92(2) . . ?
H11A O11 H11B 105(2) . . ?
H12A O12 H12B 100(2) . . ?
H13A O13 H13B 97(3) . . ?
H13C O13A H13D 96(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 O1 N1 C1 126.64(16) . . . . ?
Co1 O1 N1 C6 -54.5(2) . . . . ?
Co1 O4 C7 O5 160.86(19) . . . . ?
Co1 O4 C7 C6 -22.3(3) . . . . ?
Co1 N2 C8 C9 -179.02(17) . . . . ?
Co1 N2 C12 C11 179.95(16) . . . . ?
Co1 N2 C12 C16 -0.5(2) . . . . ?
Co1 N3 C16 C12 -3.7(2) . . . . ?
Co1 N3 C16 C15 178.00(17) . . . . ?
Co1 N3 C19 C18 -177.01(18) . . . . ?
O1 N1 C1 C2 -176.98(18) . . . . ?
O1 N1 C6 C5 177.85(19) . . . . ?
O1 N1 C6 C7 -0.7(3) . . . . ?
N1 C1 C2 C3 178.11(19) . . . . ?
N1 C1 C2 C4 -1.1(3) . . . . ?
N1 C6 C7 O4 45.6(3) . . . . ?
N1 C6 C7 O5 -137.2(2) . . . . ?
N2 C8 C9 C10 -0.2(4) . . . . ?
N2 C12 C16 N3 2.8(3) . . . . ?
N2 C12 C16 C15 -178.80(19) . . . . ?
C1 N1 C6 C5 -3.4(3) . . . . ?
C1 N1 C6 C7 178.04(19) . . . . ?
C1 C2 C3 O2 19.2(3) . . . . ?
C1 C2 C3 O3 -161.1(2) . . . . ?
C1 C2 C4 C5 -2.6(3) . . . . ?
C2 C4 C5 C6 3.4(4) . . . . ?
C3 C2 C4 C5 178.2(2) . . . . ?
C4 C2 C3 O2 -161.6(2) . . . . ?
C4 C2 C3 O3 18.1(3) . . . . ?
C4 C5 C6 N1 -0.5(3) . . . . ?
C4 C5 C6 C7 178.1(2) . . . . ?
C5 C6 C7 O4 -132.9(2) . . . . ?
C5 C6 C7 O5 44.2(3) . . . . ?
C6 N1 C1 C2 4.2(3) . . . . ?
C8 N2 C12 C11 0.9(3) . . . . ?
C8 N2 C12 C16 -179.55(19) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C9 C10 C11 C13 -179.4(2) . . . . ?
C10 C11 C12 N2 -1.3(3) . . . . ?
C10 C11 C12 C16 179.1(2) . . . . ?
C10 C11 C13 C14 180.0(2) . . . . ?
C11 C12 C16 N3 -177.59(19) . . . . ?
C11 C12 C16 C15 0.8(3) . . . . ?
C11 C13 C14 C15 1.1(4) . . . . ?
C12 N2 C8 C9 -0.1(3) . . . . ?
C12 C11 C13 C14 -0.4(3) . . . . ?
C13 C11 C12 N2 179.1(2) . . . . ?
C13 C11 C12 C16 -0.5(3) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
C13 C14 C15 C17 178.8(2) . . . . ?
C14 C15 C16 N3 178.1(2) . . . . ?
C14 C15 C16 C12 -0.2(3) . . . . ?
C14 C15 C17 C18 -178.3(2) . . . . ?
C15 C17 C18 C19 -0.9(4) . . . . ?
C16 N3 C19 C18 -0.7(3) . . . . ?
C16 C15 C17 C18 1.3(3) . . . . ?
C17 C15 C16 N3 -1.5(3) . . . . ?
C17 C15 C16 C12 -179.8(2) . . . . ?
C17 C18 C19 N3 0.6(4) . . . . ?
C19 N3 C16 C12 179.5(2) . . . . ?
C19 N3 C16 C15 1.2(3) . . . . ?
O8 C22 C23 O9 -132(3) . . . . ?
O14 C22 C23 O9 -127(3) . . . . ?
C23 O9 C22 O8 75(4) . . . . ?
C23 O9 C22 O14 71(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_khd284b
_database_code_depnum_ccdc_archive 'CCDC 1554226'
_audit_update_record             
;
2017-06-04 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H11 N Ni O9'
_chemical_formula_sum            'C7 H11 N Ni O9'
_chemical_formula_weight         311.86

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'
Ni Ni 0.3393 1.1124 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.858(2)
_cell_length_b                   10.656(2)
_cell_length_c                   11.692(2)
_cell_angle_alpha                68.85(3)
_cell_angle_beta                 84.18(3)
_cell_angle_gamma                66.00(3)
_cell_volume                     1045.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5590
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      29.20

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    1.902
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4497
_exptl_absorpt_correction_T_max  0.7022
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11560
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         29.20
_reflns_number_total             5590
_reflns_number_gt                4424
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0420P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5590
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0742
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.74091(2) 0.23721(2) 0.369149(19) 0.01616(7) Uani 1 1 d . . .
O1 O 0.80370(14) 0.12458(13) 0.55367(11) 0.0199(3) Uani 1 1 d . . .
O2 O 0.59483(17) 0.13928(15) 0.95444(13) 0.0295(3) Uani 1 1 d . . .
O3 O 0.52991(16) 0.37291(15) 0.93345(13) 0.0278(3) Uani 1 1 d . . .
O4 O 0.88499(15) 0.33133(15) 0.37109(12) 0.0241(3) Uani 1 1 d . . .
O5 O 1.06656(17) 0.3182(2) 0.47873(14) 0.0383(4) Uani 1 1 d . . .
O6 O 0.56951(15) 0.40862(14) 0.39476(12) 0.0241(3) Uani 1 1 d . . .
H6A H 0.5132 0.3913 0.4502 0.036 Uiso 1 1 d R . .
H6B H 0.5896 0.4704 0.4009 0.036 Uiso 1 1 d R . .
O7 O 0.69253(16) 0.34176(16) 0.18401(12) 0.0311(3) Uani 1 1 d . . .
H7A H 0.6313 0.4230 0.1516 0.047 Uiso 1 1 d R . .
H7B H 0.7398 0.3098 0.1315 0.047 Uiso 1 1 d R . .
O8 O 0.58775(14) 0.14199(15) 0.38194(12) 0.0236(3) Uani 1 1 d . . .
H8A H 0.5278 0.1541 0.4311 0.035 Uiso 1 1 d R . .
H8B H 0.6034 0.0631 0.3869 0.035 Uiso 1 1 d R . .
O9 O 0.91329(14) 0.07025(14) 0.33137(12) 0.0219(3) Uani 1 1 d . . .
H9A H 0.9702 0.0247 0.3822 0.033 Uiso 1 1 d R . .
H9B H 0.9551 0.1022 0.2695 0.033 Uiso 1 1 d R . .
N1 N 0.78777(16) 0.21271(15) 0.61837(13) 0.0160(3) Uani 1 1 d . . .
C1 C 0.71023(19) 0.19617(18) 0.72013(15) 0.0176(3) Uani 1 1 d . . .
H1 H 0.6707 0.1254 0.7441 0.021 Uiso 1 1 calc R . .
C2 C 0.68850(19) 0.28308(18) 0.78970(15) 0.0178(3) Uani 1 1 d . . .
C3 C 0.5972(2) 0.26401(19) 0.90176(16) 0.0191(3) Uani 1 1 d . . .
C4 C 0.7504(2) 0.38705(19) 0.75304(16) 0.0210(4) Uani 1 1 d . . .
H4 H 0.7353 0.4486 0.7970 0.025 Uiso 1 1 calc R . .
C5 C 0.8346(2) 0.3979(2) 0.65040(17) 0.0223(4) Uani 1 1 d . . .
H5 H 0.8798 0.4642 0.6274 0.027 Uiso 1 1 calc R . .
C6 C 0.85213(19) 0.31061(19) 0.58184(16) 0.0184(3) Uani 1 1 d . . .
C7 C 0.9427(2) 0.3201(2) 0.46815(17) 0.0214(4) Uani 1 1 d . . .
Ni2 Ni 0.23177(2) 0.24362(2) 0.152927(19) 0.01616(7) Uani 1 1 d . . .
O10 O 0.17471(15) 0.36648(13) -0.02861(11) 0.0205(3) Uani 1 1 d . . .
O11 O 0.40188(17) 0.35142(16) -0.41919(14) 0.0309(3) Uani 1 1 d . . .
O12 O 0.40317(18) 0.14794(16) -0.43388(14) 0.0328(3) Uani 1 1 d . . .
O13 O 0.07963(15) 0.15925(15) 0.14462(12) 0.0250(3) Uani 1 1 d . . .
O14 O -0.11253(16) 0.20713(19) 0.02910(13) 0.0337(3) Uani 1 1 d . . .
O15 O 0.06324(15) 0.41545(14) 0.18691(12) 0.0248(3) Uani 1 1 d . . .
H15A H 0.0186 0.3879 0.2419 0.037 Uiso 1 1 d R . .
H15B H 0.0048 0.4625 0.1268 0.037 Uiso 1 1 d R . .
O16 O 0.38566(15) 0.32691(14) 0.15122(12) 0.0242(3) Uani 1 1 d . . .
H16A H 0.4548 0.2823 0.2040 0.036 Uiso 1 1 d R . .
H16B H 0.4288 0.3432 0.0888 0.036 Uiso 1 1 d R . .
O17 O 0.26462(16) 0.13759(15) 0.34110(12) 0.0266(3) Uani 1 1 d . . .
H17A H 0.2256 0.1798 0.3838 0.040 Uiso 1 1 d R . .
H17B H 0.2554 0.0618 0.3715 0.040 Uiso 1 1 d R . .
O18 O 0.40258(15) 0.07297(14) 0.12011(12) 0.0244(3) Uani 1 1 d . . .
H18A H 0.4670 0.0972 0.0693 0.037 Uiso 1 1 d R . .
H18B H 0.3875 0.0193 0.0969 0.037 Uiso 1 1 d R . .
N2 N 0.18351(16) 0.28679(15) -0.09799(13) 0.0163(3) Uani 1 1 d . . .
C8 C 0.26289(19) 0.30369(19) -0.19919(15) 0.0181(3) Uani 1 1 d . . .
H8 H 0.3099 0.3682 -0.2185 0.022 Uiso 1 1 calc R . .
C9 C 0.2745(2) 0.22535(19) -0.27424(15) 0.0186(3) Uani 1 1 d . . .
C10 C 0.3670(2) 0.2435(2) -0.38540(16) 0.0205(4) Uani 1 1 d . . .
C11 C 0.2009(2) 0.1317(2) -0.24461(17) 0.0232(4) Uani 1 1 d . . .
H11 H 0.2089 0.0765 -0.2929 0.028 Uiso 1 1 calc R . .
C12 C 0.1158(2) 0.1211(2) -0.14310(18) 0.0244(4) Uani 1 1 d . . .
H12 H 0.0636 0.0611 -0.1247 0.029 Uiso 1 1 calc R . .
C13 C 0.10783(19) 0.19872(19) -0.06892(16) 0.0184(3) Uani 1 1 d . . .
C14 C 0.0157(2) 0.1905(2) 0.04333(16) 0.0204(3) 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
Ni1 O6 2.0156(15) . ?
Ni1 O7 2.0472(15) . ?
Ni1 O9 2.0503(15) . ?
Ni1 O4 2.0507(14) . ?
Ni1 O1 2.0679(14) . ?
Ni1 O8 2.1030(14) . ?
O1 N1 1.3591(18) . ?
O2 C3 1.256(2) . ?
O3 C3 1.248(2) . ?
O4 C7 1.266(2) . ?
O5 C7 1.231(2) . ?
O6 H6A 0.8280 . ?
O6 H6B 0.7878 . ?
O7 H7A 0.8011 . ?
O7 H7B 0.8215 . ?
O8 H8A 0.7868 . ?
O8 H8B 0.7717 . ?
O9 H9A 0.7354 . ?
O9 H9B 0.8274 . ?
N1 C1 1.344(2) . ?
N1 C6 1.355(2) . ?
C1 C2 1.383(2) . ?
C1 H1 0.9300 . ?
C2 C4 1.392(3) . ?
C2 C3 1.512(2) . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.520(3) . ?
Ni2 O16 2.0410(14) . ?
Ni2 O18 2.0424(15) . ?
Ni2 O10 2.0429(15) . ?
Ni2 O15 2.0462(15) . ?
Ni2 O13 2.0632(15) . ?
Ni2 O17 2.0676(15) . ?
O10 N2 1.3452(18) . ?
O11 C10 1.250(2) . ?
O12 C10 1.251(2) . ?
O13 C14 1.267(2) . ?
O14 C14 1.224(2) . ?
O15 H15A 0.7776 . ?
O15 H15B 0.8187 . ?
O16 H16A 0.8258 . ?
O16 H16B 0.8058 . ?
O17 H17A 0.7628 . ?
O17 H17B 0.7959 . ?
O18 H18A 0.8766 . ?
O18 H18B 0.7824 . ?
N2 C8 1.348(2) . ?
N2 C13 1.357(2) . ?
C8 C9 1.382(2) . ?
C8 H8 0.9300 . ?
C9 C11 1.390(3) . ?
C9 C10 1.510(2) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.515(2) . ?

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
O6 Ni1 O7 88.30(7) . . ?
O6 Ni1 O9 176.37(5) . . ?
O7 Ni1 O9 88.10(7) . . ?
O6 Ni1 O4 90.46(6) . . ?
O7 Ni1 O4 93.38(7) . . ?
O9 Ni1 O4 89.31(6) . . ?
O6 Ni1 O1 95.04(6) . . ?
O7 Ni1 O1 176.32(5) . . ?
O9 Ni1 O1 88.55(6) . . ?
O4 Ni1 O1 85.04(6) . . ?
O6 Ni1 O8 86.81(6) . . ?
O7 Ni1 O8 90.59(7) . . ?
O9 Ni1 O8 93.67(6) . . ?
O4 Ni1 O8 175.11(5) . . ?
O1 Ni1 O8 91.16(6) . . ?
N1 O1 Ni1 113.87(9) . . ?
C7 O4 Ni1 123.98(12) . . ?
Ni1 O6 H6A 118.2 . . ?
Ni1 O6 H6B 116.0 . . ?
H6A O6 H6B 107.0 . . ?
Ni1 O7 H7A 125.5 . . ?
Ni1 O7 H7B 124.5 . . ?
H7A O7 H7B 109.7 . . ?
Ni1 O8 H8A 115.4 . . ?
Ni1 O8 H8B 128.4 . . ?
H8A O8 H8B 101.6 . . ?
Ni1 O9 H9A 112.8 . . ?
Ni1 O9 H9B 111.3 . . ?
H9A O9 H9B 107.6 . . ?
C1 N1 C6 121.92(16) . . ?
C1 N1 O1 117.79(14) . . ?
C6 N1 O1 120.27(14) . . ?
N1 C1 C2 120.85(16) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C4 118.61(16) . . ?
C1 C2 C3 119.35(16) . . ?
C4 C2 C3 122.04(16) . . ?
O3 C3 O2 125.60(17) . . ?
O3 C3 C2 117.68(16) . . ?
O2 C3 C2 116.72(16) . . ?
C5 C4 C2 119.30(17) . . ?
C5 C4 H4 120.3 . . ?
C2 C4 H4 120.3 . . ?
C6 C5 C4 120.49(17) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N1 C6 C5 118.77(16) . . ?
N1 C6 C7 119.20(16) . . ?
C5 C6 C7 122.03(17) . . ?
O5 C7 O4 125.61(18) . . ?
O5 C7 C6 116.25(17) . . ?
O4 C7 C6 118.13(16) . . ?
O16 Ni2 O18 86.40(6) . . ?
O16 Ni2 O10 90.81(6) . . ?
O18 Ni2 O10 94.53(6) . . ?
O16 Ni2 O15 92.67(6) . . ?
O18 Ni2 O15 179.01(6) . . ?
O10 Ni2 O15 85.82(6) . . ?
O16 Ni2 O13 176.69(5) . . ?
O18 Ni2 O13 91.76(6) . . ?
O10 Ni2 O13 86.59(6) . . ?
O15 Ni2 O13 89.18(6) . . ?
O16 Ni2 O17 91.16(6) . . ?
O18 Ni2 O17 92.47(7) . . ?
O10 Ni2 O17 172.84(5) . . ?
O15 Ni2 O17 87.21(7) . . ?
O13 Ni2 O17 91.68(6) . . ?
N2 O10 Ni2 113.52(10) . . ?
C14 O13 Ni2 120.98(12) . . ?
Ni2 O15 H15A 111.2 . . ?
Ni2 O15 H15B 108.5 . . ?
H15A O15 H15B 106.6 . . ?
Ni2 O16 H16A 120.2 . . ?
Ni2 O16 H16B 116.2 . . ?
H16A O16 H16B 101.9 . . ?
Ni2 O17 H17A 119.9 . . ?
Ni2 O17 H17B 119.3 . . ?
H17A O17 H17B 104.1 . . ?
Ni2 O18 H18A 115.2 . . ?
Ni2 O18 H18B 121.3 . . ?
H18A O18 H18B 103.1 . . ?
O10 N2 C8 117.80(15) . . ?
O10 N2 C13 120.12(14) . . ?
C8 N2 C13 121.99(15) . . ?
N2 C8 C9 120.16(17) . . ?
N2 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C11 118.82(17) . . ?
C8 C9 C10 119.16(17) . . ?
C11 C9 C10 122.02(17) . . ?
O11 C10 O12 126.23(18) . . ?
O11 C10 C9 116.91(17) . . ?
O12 C10 C9 116.86(17) . . ?
C12 C11 C9 119.63(17) . . ?
C12 C11 H11 120.2 . . ?
C9 C11 H11 120.2 . . ?
C13 C12 C11 120.35(18) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
N2 C13 C12 118.97(16) . . ?
N2 C13 C14 118.89(16) . . ?
C12 C13 C14 122.13(17) . . ?
O14 C14 O13 125.59(18) . . ?
O14 C14 C13 116.60(17) . . ?
O13 C14 C13 117.69(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
O6 Ni1 O1 N1 -36.42(12) . . . . ?
O7 Ni1 O1 N1 118.3(9) . . . . ?
O9 Ni1 O1 N1 143.03(11) . . . . ?
O4 Ni1 O1 N1 53.60(11) . . . . ?
O8 Ni1 O1 N1 -123.32(11) . . . . ?
O6 Ni1 O4 C7 83.67(16) . . . . ?
O7 Ni1 O4 C7 171.99(15) . . . . ?
O9 Ni1 O4 C7 -99.96(16) . . . . ?
O1 Ni1 O4 C7 -11.35(15) . . . . ?
O8 Ni1 O4 C7 27.7(7) . . . . ?
Ni1 O1 N1 C1 127.40(13) . . . . ?
Ni1 O1 N1 C6 -54.32(17) . . . . ?
C6 N1 C1 C2 2.4(2) . . . . ?
O1 N1 C1 C2 -179.39(14) . . . . ?
N1 C1 C2 C4 -0.8(2) . . . . ?
N1 C1 C2 C3 178.41(15) . . . . ?
C1 C2 C3 O3 -151.93(17) . . . . ?
C4 C2 C3 O3 27.3(3) . . . . ?
C1 C2 C3 O2 27.4(2) . . . . ?
C4 C2 C3 O2 -153.37(18) . . . . ?
C1 C2 C4 C5 -1.6(3) . . . . ?
C3 C2 C4 C5 179.13(16) . . . . ?
C2 C4 C5 C6 2.7(3) . . . . ?
C1 N1 C6 C5 -1.3(2) . . . . ?
O1 N1 C6 C5 -179.50(15) . . . . ?
C1 N1 C6 C7 177.94(15) . . . . ?
O1 N1 C6 C7 -0.3(2) . . . . ?
C4 C5 C6 N1 -1.3(3) . . . . ?
C4 C5 C6 C7 179.54(16) . . . . ?
Ni1 O4 C7 O5 148.23(17) . . . . ?
Ni1 O4 C7 C6 -32.9(2) . . . . ?
N1 C6 C7 O5 -131.1(2) . . . . ?
C5 C6 C7 O5 48.1(3) . . . . ?
N1 C6 C7 O4 49.9(2) . . . . ?
C5 C6 C7 O4 -130.89(19) . . . . ?
O16 Ni2 O10 N2 125.49(11) . . . . ?
O18 Ni2 O10 N2 39.04(12) . . . . ?
O15 Ni2 O10 N2 -141.88(12) . . . . ?
O13 Ni2 O10 N2 -52.46(11) . . . . ?
O17 Ni2 O10 N2 -128.6(4) . . . . ?
O16 Ni2 O13 C14 -31.8(10) . . . . ?
O18 Ni2 O13 C14 -88.02(15) . . . . ?
O10 Ni2 O13 C14 6.42(15) . . . . ?
O15 Ni2 O13 C14 92.27(15) . . . . ?
O17 Ni2 O13 C14 179.46(15) . . . . ?
Ni2 O10 N2 C8 -127.89(13) . . . . ?
Ni2 O10 N2 C13 55.43(17) . . . . ?
O10 N2 C8 C9 -179.47(15) . . . . ?
C13 N2 C8 C9 -2.9(2) . . . . ?
N2 C8 C9 C11 1.2(3) . . . . ?
N2 C8 C9 C10 -178.57(15) . . . . ?
C8 C9 C10 O11 -15.2(2) . . . . ?
C11 C9 C10 O11 165.01(18) . . . . ?
C8 C9 C10 O12 163.82(17) . . . . ?
C11 C9 C10 O12 -15.9(3) . . . . ?
C8 C9 C11 C12 1.3(3) . . . . ?
C10 C9 C11 C12 -178.93(17) . . . . ?
C9 C11 C12 C13 -2.3(3) . . . . ?
O10 N2 C13 C12 178.44(15) . . . . ?
C8 N2 C13 C12 1.9(3) . . . . ?
O10 N2 C13 C14 -0.8(2) . . . . ?
C8 N2 C13 C14 -177.37(15) . . . . ?
C11 C12 C13 N2 0.7(3) . . . . ?
C11 C12 C13 C14 179.93(17) . . . . ?
Ni2 O13 C14 O14 -144.72(17) . . . . ?
Ni2 O13 C14 C13 39.4(2) . . . . ?
N2 C13 C14 O14 130.11(19) . . . . ?
C12 C13 C14 O14 -49.1(3) . . . . ?
N2 C13 C14 O13 -53.7(2) . . . . ?
C12 C13 C14 O13 127.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        29.20
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.083
