# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1549987'
_audit_update_record             
;
2017-09-13 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H58 N8 Ni3 O24'
_chemical_formula_weight         1379.21

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   7.096(5)
_cell_length_b                   13.946(5)
_cell_length_c                   15.121(5)
_cell_angle_alpha                78.028(5)
_cell_angle_beta                 79.552(5)
_cell_angle_gamma                88.318(5)
_cell_volume                     1439.5(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6130
_cell_measurement_theta_min      2.2465
_cell_measurement_theta_max      27.5488

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_F_000             714
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.063
_shelx_estimated_absorpt_T_min   0.800
_shelx_estimated_absorpt_T_max   0.848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5627
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12793
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.246
_diffrn_reflns_theta_max         27.599
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             6592
_reflns_number_gt                5378
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0358P)²+1.2486P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6592
_refine_ls_number_parameters     403
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      147.459
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 1.000000 0.000000 0.500000 0.01589(11) Uani 1 2 d S . P . .
Ni2 Ni 0.59855(5) 0.25494(2) 1.13338(2) 0.01847(10) Uani 1 1 d . . . . .
N1 N 0.5964(3) 0.28876(15) 1.25885(14) 0.0230(5) Uani 1 1 d . . . . .
N2 N 0.5775(4) 0.26323(16) 1.40822(15) 0.0301(5) Uani 1 1 d . . . . .
H2 H 0.577231 0.232638 1.463816 0.036 Uiso 1 1 calc R U . . .
N3 N 0.9612(3) -0.14812(14) 0.54336(14) 0.0225(5) Uani 1 1 d . . . . .
N4 N 0.9373(4) -0.29355(15) 0.63424(15) 0.0278(5) Uani 1 1 d . . . . .
H4 H 0.923967 -0.337732 0.683979 0.033 Uiso 1 1 calc R U . . .
O1 O 0.6027(3) 0.21269(15) 1.01005(12) 0.0283(4) Uani 1 1 d . . . . .
O2 O 0.2968(3) 0.16880(17) 1.02453(14) 0.0383(5) Uani 1 1 d . . . . .
O3 O 0.8197(3) 0.02259(12) 0.61719(12) 0.0235(4) Uani 1 1 d . . . . .
O4 O 0.5731(3) 0.10489(14) 0.56402(12) 0.0262(4) Uani 1 1 d . . . . .
O5 O -0.0906(3) 0.58899(13) 0.82746(14) 0.0317(5) Uani 1 1 d . . . . .
O6 O -0.3248(3) 0.47750(14) 0.87959(14) 0.0303(5) Uani 1 1 d . . . . .
O7 O 0.8979(3) 0.27837(15) 1.09566(16) 0.0366(5) Uani 1 1 d . . . . .
H7A H 0.949273 0.320968 1.115834 0.044 Uiso 1 1 d R U . . .
H7B H 0.948573 0.277068 1.038433 0.044 Uiso 1 1 d R U . . .
O8 O 0.5781(3) 0.39678(14) 1.06821(13) 0.0324(5) Uani 1 1 d . . . . .
H8A H 0.476757 0.419651 1.090085 0.049 Uiso 1 1 d R U . . .
H8B H 0.597012 0.400154 1.018090 0.039 Uiso 1 1 d R U . . .
O9 O 0.3057(3) 0.23719(14) 1.16985(12) 0.0279(4) Uani 1 1 d . . . . .
H9A H 0.262991 0.222617 1.127453 0.042 Uiso 1 1 d R U . . .
H9B H 0.238608 0.292490 1.167013 0.033 Uiso 1 1 d R U . . .
O10 O 1.2381(3) -0.01247(13) 0.56856(12) 0.0265(4) Uani 1 1 d . . . . .
H10B H 1.327692 -0.037661 0.539312 0.040 Uiso 1 1 d R U . . .
H10A H 1.293989 0.037370 0.577473 0.032 Uiso 1 1 d R U . . .
O11 O 0.9548(4) 0.0716(3) 0.0538(3) 0.1199(18) Uani 1 1 d . . . . .
H11B H 0.916319 0.080887 0.002666 0.180 Uiso 1 1 d DR U . . .
H11C H 1.047019 0.110717 0.049806 0.180 Uiso 1 1 d R U . . .
O12 O 0.6572(3) 0.10782(14) 1.18596(14) 0.0390(5) Uani 1 1 d . . . . .
H12B H 0.752894 0.088558 1.148419 0.047 Uiso 1 1 d R U . . .
H12A H 0.565794 0.061558 1.198221 0.047 Uiso 1 1 d R U . . .
C1 C 0.6046(5) 0.2226(2) 1.33440(18) 0.0303(6) Uani 1 1 d . . . . .
H1 H 0.626429 0.156228 1.335989 0.036 Uiso 1 1 calc R U . . .
C2 C 0.5602(4) 0.37601(19) 1.28782(17) 0.0246(6) Uani 1 1 d . . . . .
H2A H 0.544814 0.436009 1.249442 0.030 Uiso 1 1 calc R U . . .
C3 C 0.5499(4) 0.36219(19) 1.38053(17) 0.0220(5) Uani 1 1 d . . . . .
C4 C 0.5219(4) 0.43154(19) 1.44254(17) 0.0217(5) Uani 1 1 d . . . . .
C5 C 0.4796(4) 0.5291(2) 1.40946(18) 0.0272(6) Uani 1 1 d . . . . .
H5 H 0.465079 0.549110 1.348478 0.033 Uiso 1 1 calc R U . . .
C6 C 0.4589(4) 0.5963(2) 1.46549(18) 0.0267(6) Uani 1 1 d . . . . .
H6 H 0.431704 0.661151 1.441690 0.032 Uiso 1 1 calc R U . . .
C7 C 0.4655(4) 0.18158(19) 0.98166(17) 0.0219(5) Uani 1 1 d . . . . .
C8 C 0.5107(4) 0.15485(19) 0.88846(17) 0.0218(5) Uani 1 1 d . . . . .
C9 C 0.6575(4) 0.0880(2) 0.87327(18) 0.0286(6) Uani 1 1 d . . . . .
H9 H 0.723264 0.061361 0.920448 0.034 Uiso 1 1 calc DR U . . .
C10 C 0.7065(4) 0.0609(2) 0.78956(18) 0.0263(6) Uani 1 1 d . . . . .
H10 H 0.805162 0.016693 0.780424 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6088(4) 0.09951(17) 0.71901(17) 0.0190(5) Uani 1 1 d . . . . .
C12 C 0.6704(4) 0.07353(17) 0.62614(16) 0.0193(5) Uani 1 1 d . . . . .
C13 C 0.4588(4) 0.16496(18) 0.73376(17) 0.0197(5) Uani 1 1 d . . . . .
H13 H 0.391038 0.189472 0.686837 0.024 Uiso 1 1 calc R U . . .
C14 C 0.4094(3) 0.19397(17) 0.81774(17) 0.0193(5) Uani 1 1 d . . . . .
C15 C 0.2603(4) 0.27077(18) 0.82919(17) 0.0201(5) Uani 1 1 d . . . . .
C16 C 0.0767(4) 0.26058(19) 0.8124(2) 0.0269(6) Uani 1 1 d . . . . .
H16 H 0.043650 0.204296 0.794603 0.032 Uiso 1 1 calc R U . . .
C17 C 0.3064(4) 0.3554(2) 0.8553(2) 0.0280(6) Uani 1 1 d . . . . .
H17 H 0.427796 0.362542 0.868289 0.034 Uiso 1 1 calc R U . . .
C18 C -0.0583(4) 0.3340(2) 0.8219(2) 0.0272(6) Uani 1 1 d . . . . .
H18 H -0.182174 0.325498 0.812598 0.033 Uiso 1 1 calc R U . . .
C19 C 0.1731(4) 0.42981(19) 0.8622(2) 0.0279(6) Uani 1 1 d . . . . .
H19 H 0.207193 0.486895 0.878290 0.033 Uiso 1 1 calc R U . . .
C20 C -0.0088(4) 0.41974(18) 0.84534(17) 0.0215(5) Uani 1 1 d . . . . .
C21 C -0.1516(4) 0.50176(18) 0.85146(17) 0.0215(5) Uani 1 1 d . . . . .
C22 C 0.9363(4) -0.19567(18) 0.62893(18) 0.0282(6) Uani 1 1 d . . . . .
H22 H 0.920134 -0.165962 0.679442 0.034 Uiso 1 1 calc R U . . .
C23 C 0.9773(4) -0.21923(18) 0.49146(18) 0.0236(6) Uani 1 1 d . . . . .
H23 H 0.995197 -0.206867 0.427639 0.028 Uiso 1 1 calc R U . . .
C24 C 0.9632(4) -0.31030(17) 0.54677(17) 0.0209(5) Uani 1 1 d . . . . .
C25 C 0.9787(4) -0.40785(17) 0.52418(18) 0.0203(5) Uani 1 1 d . . . . .
C26 C 0.9627(4) -0.41871(18) 0.43640(19) 0.0248(6) Uani 1 1 d . . . . .
H26 H 0.936752 -0.364213 0.393373 0.030 Uiso 1 1 calc R U . . .
C27 C 1.0152(4) -0.49080(18) 0.58788(18) 0.0235(5) Uani 1 1 d . . . . .
H27 H 1.024879 -0.485214 0.647133 0.028 Uiso 1 1 calc R U . . .


_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 N3 2.044(2) . ?
Ni1 N3 2.044(2) 2_756 ?
Ni1 O3 2.0644(17) . ?
Ni1 O3 2.0644(17) 2_756 ?
Ni1 O10 2.122(2) . ?
Ni1 O10 2.122(2) 2_756 ?
Ni2 O8 2.032(2) . ?
Ni2 N1 2.045(2) . ?
Ni2 O9 2.059(2) . ?
Ni2 O1 2.0643(19) . ?
Ni2 O12 2.100(2) . ?
Ni2 O7 2.114(2) . ?
N1 C1 1.320(3) . ?
N1 C2 1.379(3) . ?
N2 C1 1.335(3) . ?
N2 C3 1.376(3) . ?
N2 H2 0.8600 . ?
N3 C22 1.309(3) . ?
N3 C23 1.377(3) . ?
N4 C22 1.350(3) . ?
N4 C24 1.369(3) . ?
N4 H4 0.8600 . ?
O1 C7 1.254(3) . ?
O2 C7 1.252(3) . ?
O3 C12 1.261(3) . ?
O4 C12 1.264(3) . ?
O5 C21 1.261(3) . ?
O6 C21 1.257(3) . ?
O7 H7A 0.8409 . ?
O7 H7B 0.8785 . ?
O8 H8A 0.8200 . ?
O8 H8B 0.7371 . ?
O9 H9A 0.8200 . ?
O9 H9B 0.8921 . ?
O10 H10B 0.8200 . ?
O10 H10A 0.8562 . ?
O11 H11B 0.8500 . ?
O11 H11C 0.8500 . ?
O12 H12B 0.8763 . ?
O12 H12A 0.8961 . ?
C1 H1 0.9300 . ?
C2 C3 1.364(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.467(3) . ?
C4 C5 1.392(4) . ?
C4 C6 1.394(4) 2_668 ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.508(3) . ?
C8 C9 1.398(3) . ?
C8 C14 1.404(4) . ?
C9 C10 1.377(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9300 . ?
C11 C13 1.399(3) . ?
C11 C12 1.508(3) . ?
C13 C14 1.394(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.497(3) . ?
C15 C17 1.385(4) . ?
C15 C16 1.388(4) . ?
C16 C18 1.393(3) . ?
C16 H16 0.9300 . ?
C17 C19 1.391(3) . ?
C17 H17 0.9300 . ?
C18 C20 1.387(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.512(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.364(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.466(3) . ?
C25 C26 1.392(4) . ?
C25 C27 1.394(3) . ?
C26 C27 1.383(3) 2_746 ?
C26 H26 0.9300 . ?
C27 H27 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
N3 Ni1 N3 180.0 . 2_756 ?
N3 Ni1 O3 90.25(7) . . ?
N3 Ni1 O3 89.75(7) 2_756 . ?
N3 Ni1 O3 89.75(7) . 2_756 ?
N3 Ni1 O3 90.25(8) 2_756 2_756 ?
O3 Ni1 O3 180.0 . 2_756 ?
N3 Ni1 O10 87.97(8) . . ?
N3 Ni1 O10 92.03(8) 2_756 . ?
O3 Ni1 O10 90.66(8) . . ?
O3 Ni1 O10 89.34(8) 2_756 . ?
N3 Ni1 O10 92.03(8) . 2_756 ?
N3 Ni1 O10 87.97(8) 2_756 2_756 ?
O3 Ni1 O10 89.34(8) . 2_756 ?
O3 Ni1 O10 90.66(8) 2_756 2_756 ?
O10 Ni1 O10 180.0 . 2_756 ?
O8 Ni2 N1 94.18(8) . . ?
O8 Ni2 O9 92.98(8) . . ?
N1 Ni2 O9 87.66(8) . . ?
O8 Ni2 O1 89.03(8) . . ?
N1 Ni2 O1 176.79(8) . . ?
O9 Ni2 O1 92.33(8) . . ?
O8 Ni2 O12 171.36(8) . . ?
N1 Ni2 O12 90.63(8) . . ?
O9 Ni2 O12 94.38(9) . . ?
O1 Ni2 O12 86.17(8) . . ?
O8 Ni2 O7 85.24(9) . . ?
N1 Ni2 O7 91.67(9) . . ?
O9 Ni2 O7 178.05(8) . . ?
O1 Ni2 O7 88.44(8) . . ?
O12 Ni2 O7 87.46(9) . . ?
C1 N1 C2 105.0(2) . . ?
C1 N1 Ni2 123.69(18) . . ?
C2 N1 Ni2 130.65(17) . . ?
C1 N2 C3 108.6(2) . . ?
C1 N2 H2 125.7 . . ?
C3 N2 H2 125.7 . . ?
C22 N3 C23 105.5(2) . . ?
C22 N3 Ni1 125.47(18) . . ?
C23 N3 Ni1 128.64(17) . . ?
C22 N4 C24 108.2(2) . . ?
C22 N4 H4 125.9 . . ?
C24 N4 H4 125.9 . . ?
C7 O1 Ni2 127.93(16) . . ?
C12 O3 Ni1 130.22(16) . . ?
Ni2 O7 H7A 119.1 . . ?
Ni2 O7 H7B 116.4 . . ?
H7A O7 H7B 112.5 . . ?
Ni2 O8 H8A 109.5 . . ?
Ni2 O8 H8B 109.6 . . ?
H8A O8 H8B 116.7 . . ?
Ni2 O9 H9A 109.5 . . ?
Ni2 O9 H9B 115.5 . . ?
H9A O9 H9B 92.5 . . ?
Ni1 O10 H10B 109.5 . . ?
Ni1 O10 H10A 122.7 . . ?
H10B O10 H10A 100.9 . . ?
H11B O11 H11C 109.5 . . ?
Ni2 O12 H12B 108.7 . . ?
Ni2 O12 H12A 120.9 . . ?
H12B O12 H12A 106.6 . . ?
N1 C1 N2 111.3(2) . . ?
N1 C1 H1 124.4 . . ?
N2 C1 H1 124.4 . . ?
C3 C2 N1 110.6(2) . . ?
C3 C2 H2A 124.7 . . ?
N1 C2 H2A 124.7 . . ?
C2 C3 N2 104.4(2) . . ?
C2 C3 C4 131.4(2) . . ?
N2 C3 C4 124.2(2) . . ?
C5 C4 C6 118.0(2) . 2_668 ?
C5 C4 C3 120.0(2) . . ?
C6 C4 C3 122.0(2) 2_668 . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C4 120.9(2) . 2_668 ?
C5 C6 H6 119.5 . . ?
C4 C6 H6 119.5 2_668 . ?
O2 C7 O1 125.9(2) . . ?
O2 C7 C8 117.6(2) . . ?
O1 C7 C8 116.5(2) . . ?
C9 C8 C14 119.5(2) . . ?
C9 C8 C7 118.2(2) . . ?
C14 C8 C7 122.3(2) . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C13 119.6(2) . . ?
C10 C11 C12 119.6(2) . . ?
C13 C11 C12 120.8(2) . . ?
O3 C12 O4 125.5(2) . . ?
O3 C12 C11 115.8(2) . . ?
O4 C12 C11 118.8(2) . . ?
C14 C13 C11 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C11 C13 H13 119.5 . . ?
C13 C14 C8 118.8(2) . . ?
C13 C14 C15 120.0(2) . . ?
C8 C14 C15 121.1(2) . . ?
C17 C15 C16 118.7(2) . . ?
C17 C15 C14 119.6(2) . . ?
C16 C15 C14 121.7(2) . . ?
C15 C16 C18 120.5(2) . . ?
C15 C16 H16 119.7 . . ?
C18 C16 H16 119.7 . . ?
C15 C17 C19 120.7(3) . . ?
C15 C17 H17 119.7 . . ?
C19 C17 H17 119.7 . . ?
C20 C18 C16 120.3(3) . . ?
C20 C18 H18 119.9 . . ?
C16 C18 H18 119.9 . . ?
C20 C19 C17 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C17 C19 H19 119.7 . . ?
C19 C20 C18 119.2(2) . . ?
C19 C20 C21 120.2(2) . . ?
C18 C20 C21 120.6(2) . . ?
O6 C21 O5 124.6(2) . . ?
O6 C21 C20 117.0(2) . . ?
O5 C21 C20 118.4(2) . . ?
N3 C22 N4 111.1(2) . . ?
N3 C22 H22 124.4 . . ?
N4 C22 H22 124.4 . . ?
C24 C23 N3 110.5(2) . . ?
C24 C23 H23 124.8 . . ?
N3 C23 H23 124.8 . . ?
C23 C24 N4 104.7(2) . . ?
C23 C24 C25 130.9(2) . . ?
N4 C24 C25 124.4(2) . . ?
C26 C25 C27 118.4(2) . . ?
C26 C25 C24 119.9(2) . . ?
C27 C25 C24 121.6(2) . . ?
C27 C26 C25 121.1(2) 2_746 . ?
C27 C26 H26 119.5 2_746 . ?
C25 C26 H26 119.5 . . ?
C26 C27 C25 120.5(2) 2_746 . ?
C26 C27 H27 119.8 2_746 . ?
C25 C27 H27 119.8 . . ?

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
C2 N1 C1 N2 -0.5(3) . . . . ?
Ni2 N1 C1 N2 -172.4(2) . . . . ?
C3 N2 C1 N1 -0.1(4) . . . . ?
C1 N1 C2 C3 1.0(3) . . . . ?
Ni2 N1 C2 C3 172.11(19) . . . . ?
N1 C2 C3 N2 -1.1(3) . . . . ?
N1 C2 C3 C4 177.4(3) . . . . ?
C1 N2 C3 C2 0.7(3) . . . . ?
C1 N2 C3 C4 -177.9(3) . . . . ?
C2 C3 C4 C5 7.0(5) . . . . ?
N2 C3 C4 C5 -174.8(3) . . . . ?
C2 C3 C4 C6 -171.3(3) . . . 2_668 ?
N2 C3 C4 C6 6.9(4) . . . 2_668 ?
C6 C4 C5 C6 0.5(5) 2_668 . . . ?
C3 C4 C5 C6 -177.8(3) . . . . ?
C4 C5 C6 C4 -0.6(5) . . . 2_668 ?
Ni2 O1 C7 O2 -1.1(4) . . . . ?
Ni2 O1 C7 C8 -179.33(16) . . . . ?
O2 C7 C8 C9 -124.0(3) . . . . ?
O1 C7 C8 C9 54.4(4) . . . . ?
O2 C7 C8 C14 55.3(4) . . . . ?
O1 C7 C8 C14 -126.2(3) . . . . ?
C14 C8 C9 C10 1.0(4) . . . . ?
C7 C8 C9 C10 -179.7(3) . . . . ?
C8 C9 C10 C11 -0.5(5) . . . . ?
C9 C10 C11 C13 -0.9(4) . . . . ?
C9 C10 C11 C12 176.8(3) . . . . ?
Ni1 O3 C12 O4 17.3(4) . . . . ?
Ni1 O3 C12 C11 -161.42(17) . . . . ?
C10 C11 C12 O3 -5.1(4) . . . . ?
C13 C11 C12 O3 172.5(2) . . . . ?
C10 C11 C12 O4 176.1(3) . . . . ?
C13 C11 C12 O4 -6.3(4) . . . . ?
C10 C11 C13 C14 1.7(4) . . . . ?
C12 C11 C13 C14 -175.9(2) . . . . ?
C11 C13 C14 C8 -1.2(4) . . . . ?
C11 C13 C14 C15 174.6(2) . . . . ?
C9 C8 C14 C13 -0.1(4) . . . . ?
C7 C8 C14 C13 -179.5(2) . . . . ?
C9 C8 C14 C15 -175.8(3) . . . . ?
C7 C8 C14 C15 4.8(4) . . . . ?
C13 C14 C15 C17 -122.1(3) . . . . ?
C8 C14 C15 C17 53.5(4) . . . . ?
C13 C14 C15 C16 56.4(4) . . . . ?
C8 C14 C15 C16 -127.9(3) . . . . ?
C17 C15 C16 C18 -0.2(4) . . . . ?
C14 C15 C16 C18 -178.8(2) . . . . ?
C16 C15 C17 C19 -1.6(4) . . . . ?
C14 C15 C17 C19 177.0(2) . . . . ?
C15 C16 C18 C20 2.2(4) . . . . ?
C15 C17 C19 C20 1.6(4) . . . . ?
C17 C19 C20 C18 0.4(4) . . . . ?
C17 C19 C20 C21 -179.0(2) . . . . ?
C16 C18 C20 C19 -2.3(4) . . . . ?
C16 C18 C20 C21 177.1(2) . . . . ?
C19 C20 C21 O6 -146.4(3) . . . . ?
C18 C20 C21 O6 34.2(4) . . . . ?
C19 C20 C21 O5 34.3(4) . . . . ?
C18 C20 C21 O5 -145.1(3) . . . . ?
C23 N3 C22 N4 0.5(3) . . . . ?
Ni1 N3 C22 N4 -172.77(19) . . . . ?
C24 N4 C22 N3 -0.4(3) . . . . ?
C22 N3 C23 C24 -0.4(3) . . . . ?
Ni1 N3 C23 C24 172.54(19) . . . . ?
N3 C23 C24 N4 0.2(3) . . . . ?
N3 C23 C24 C25 -177.4(3) . . . . ?
C22 N4 C24 C23 0.1(3) . . . . ?
C22 N4 C24 C25 177.9(3) . . . . ?
C23 C24 C25 C26 -16.9(4) . . . . ?
N4 C24 C25 C26 165.9(3) . . . . ?
C23 C24 C25 C27 161.1(3) . . . . ?
N4 C24 C25 C27 -16.1(4) . . . . ?
C27 C25 C26 C27 -0.8(4) . . . 2_746 ?
C24 C25 C26 C27 177.2(2) . . . 2_746 ?
C26 C25 C27 C26 0.8(4) . . . 2_746 ?
C24 C25 C27 C26 -177.2(2) . . . 2_746 ?

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
C22 H22 O9 0.93 2.56 3.158(3) 122.1 2_657
C1 H1 O12 0.93 2.47 2.982(3) 114.8 .
C1 H1 O10 0.93 2.49 3.256(3) 139.4 2_757
O12 H12B O11 0.88 1.88 2.744(4) 168.9 1_556
O11 H11C O2 0.85 1.91 2.735(4) 162.7 1_654
O10 H10A O4 0.86 2.18 2.908(3) 143.3 1_655
O10 H10B O4 0.82 2.00 2.733(3) 149.2 2_756
O9 H9B O5 0.89 1.94 2.830(3) 174.9 2_567
O9 H9A O2 0.82 1.84 2.582(3) 150.0 .
O8 H8B O6 0.74 2.13 2.807(3) 153.1 1_655
O8 H8A O6 0.82 1.85 2.608(3) 152.6 2_567
O7 H7A O5 0.84 2.04 2.874(3) 173.3 2_667
N4 H4 O5 0.86 2.18 3.014(3) 162.2 1_645
N2 H2 O4 0.86 2.08 2.872(3) 152.2 1_556

_refine_diff_density_max         0.825
_refine_diff_density_min         -0.521
_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_2
_database_code_depnum_ccdc_archive 'CCDC 1549986'
_audit_update_record             
;
2017-09-13 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H20 Co N4 O6'
_chemical_formula_weight         555.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.4041(9)
_cell_length_b                   21.3552(16)
_cell_length_c                   10.8848(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.7010(10)
_cell_angle_gamma                90
_cell_volume                     2612.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6089
_cell_measurement_theta_min      2.6913
_cell_measurement_theta_max      27.5013

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             1140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.705
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6140
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17672
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.812
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6012
_reflns_number_gt                4756
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.9824P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6012
_refine_ls_number_parameters     343
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0932
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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_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 0.26766(2) 0.38533(2) 0.51125(2) 0.02250(9) Uani 1 1 d . . . . .
N1 N 0.32481(14) 0.44713(7) 0.38813(14) 0.0273(3) Uani 1 1 d . . . . .
N2 N 0.42045(15) 0.52665(7) 0.32282(15) 0.0311(4) Uani 1 1 d . . . . .
H2A H 0.4539 0.5627 0.3221 0.037 Uiso 1 1 calc R U . . .
N3 N 0.19731(14) 0.44311(7) 0.62905(14) 0.0273(3) Uani 1 1 d . . . . .
N4 N 0.07878(15) 0.51713(7) 0.67539(15) 0.0306(4) Uani 1 1 d . . . . .
H4 H 0.0344 0.5499 0.6675 0.037 Uiso 1 1 calc R U . . .
O1 O 0.21213(12) 0.31166(6) 0.39063(15) 0.0406(4) Uani 1 1 d . . . . .
O2 O 0.07907(12) 0.38460(6) 0.38803(13) 0.0350(3) Uani 1 1 d . . . . .
O3 O -0.56211(12) 0.36864(6) -0.39101(13) 0.0304(3) Uani 1 1 d . . . . .
O4 O -0.69535(13) 0.30551(7) -0.33840(17) 0.0462(4) Uani 1 1 d . . . . .
O5 O -0.22000(16) 0.13231(8) 0.00355(16) 0.0547(5) Uani 1 1 d . . . . .
O1W O 0.2576(3) 0.18343(12) 0.5224(3) 0.1405(15) Uani 1 1 d D . . . .
H1WA H 0.2497 0.2146 0.5689 0.169 Uiso 1 1 d DR U . . .
H1WB H 0.2863 0.2020 0.4647 0.169 Uiso 1 1 d DR U . . .
C1 C 0.36805(18) 0.50384(9) 0.41471(18) 0.0306(4) Uani 1 1 d . . . . .
H1 H 0.3628 0.5252 0.4880 0.037 Uiso 1 1 calc R U . . .
C2 C 0.35150(18) 0.43365(9) 0.27148(18) 0.0304(4) Uani 1 1 d . . . . .
H2 H 0.3314 0.3967 0.2278 0.036 Uiso 1 1 calc R U . . .
C3 C 0.41144(17) 0.48235(9) 0.22988(17) 0.0282(4) Uani 1 1 d . . . . .
C4 C 0.4590(3) 0.44292(11) 0.0306(2) 0.0597(8) Uani 1 1 d . . . . .
H4A H 0.4315 0.4037 0.0500 0.072 Uiso 1 1 calc R U . . .
C5 C 0.45752(19) 0.49163(9) 0.11320(18) 0.0324(4) Uani 1 1 d . . . . .
C6 C 0.4995(3) 0.54897(11) 0.0809(2) 0.0603(8) Uani 1 1 d . . . . .
H6 H 0.5000 0.5827 0.1350 0.072 Uiso 1 1 calc R U . . .
C7 C 0.13771(17) 0.49425(9) 0.58923(17) 0.0288(4) Uani 1 1 d . . . . .
H7 H 0.1369 0.5121 0.5111 0.035 Uiso 1 1 calc R U . . .
C8 C 0.17573(18) 0.43364(9) 0.74909(18) 0.0308(4) Uani 1 1 d . . . . .
H8 H 0.2072 0.4011 0.8013 0.037 Uiso 1 1 calc R U . . .
C9 C 0.10138(17) 0.47907(9) 0.77931(17) 0.0294(4) Uani 1 1 d . . . . .
C10 C 0.04958(19) 0.49016(10) 0.89159(18) 0.0339(5) Uani 1 1 d . . . . .
C11 C -0.0502(2) 0.52718(13) 0.8895(2) 0.0567(8) Uani 1 1 d . . . . .
H11 H -0.0852 0.5459 0.8152 0.068 Uiso 1 1 calc R U . . .
C12 C 0.0990(2) 0.46322(13) 1.0037(2) 0.0567(8) Uani 1 1 d . . . . .
H12 H 0.1662 0.4382 1.0077 0.068 Uiso 1 1 calc R U . . .
C13 C 0.10943(17) 0.33274(9) 0.35003(18) 0.0278(4) Uani 1 1 d . . . . .
C14 C 0.02434(17) 0.29546(9) 0.25774(18) 0.0297(4) Uani 1 1 d . . . . .
C15 C 0.05420(19) 0.23630(10) 0.2215(2) 0.0392(5) Uani 1 1 d . . . . .
H15 H 0.1279 0.2193 0.2544 0.047 Uiso 1 1 calc R U . . .
C16 C -0.02484(19) 0.20215(10) 0.1365(2) 0.0396(5) Uani 1 1 d . . . . .
H16 H -0.0048 0.1621 0.1138 0.048 Uiso 1 1 calc R U . . .
C17 C -0.13411(18) 0.22781(9) 0.08512(19) 0.0330(4) Uani 1 1 d . . . . .
C18 C -0.1638(2) 0.28719(10) 0.1219(2) 0.0420(5) Uani 1 1 d . . . . .
H18 H -0.2369 0.3046 0.0880 0.050 Uiso 1 1 calc R U . . .
C19 C -0.08586(19) 0.32059(10) 0.2082(2) 0.0402(5) Uani 1 1 d . . . . .
H19 H -0.1071 0.3600 0.2334 0.048 Uiso 1 1 calc R U . . .
C20 C -0.22212(19) 0.18914(10) -0.00146(19) 0.0357(5) Uani 1 1 d . . . . .
C21 C -0.31485(18) 0.22304(9) -0.09038(19) 0.0325(4) Uani 1 1 d . . . . .
C22 C -0.4316(2) 0.20136(10) -0.1079(2) 0.0401(5) Uani 1 1 d . . . . .
H22 H -0.4500 0.1651 -0.0678 0.048 Uiso 1 1 calc R U . . .
C23 C -0.52032(19) 0.23354(10) -0.1843(2) 0.0386(5) Uani 1 1 d . . . . .
H23 H -0.5987 0.2198 -0.1930 0.046 Uiso 1 1 calc R U . . .
C24 C -0.49295(17) 0.28624(9) -0.24836(18) 0.0283(4) Uani 1 1 d . . . . .
C25 C -0.37549(17) 0.30648(9) -0.2351(2) 0.0338(5) Uani 1 1 d . . . . .
H25 H -0.3561 0.3407 -0.2805 0.041 Uiso 1 1 calc R U . . .
C26 C -0.28804(18) 0.27575(10) -0.1548(2) 0.0374(5) Uani 1 1 d . . . . .
H26 H -0.2102 0.2905 -0.1436 0.045 Uiso 1 1 calc R U . . .
C27 C -0.59014(17) 0.32161(9) -0.32979(18) 0.0281(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N3 2.0389(15) . ?
Co1 N1 2.0633(15) . ?
Co1 O1 2.0784(14) . ?
Co1 O3 2.0812(13) 1_656 ?
Co1 O2 2.3351(14) . ?
Co1 O4 2.3513(16) 1_656 ?
N1 C1 1.321(2) . ?
N1 C2 1.385(2) . ?
N2 C1 1.340(2) . ?
N2 C3 1.376(2) . ?
N2 H2A 0.8600 . ?
N3 C7 1.320(2) . ?
N3 C8 1.385(2) . ?
N4 C7 1.335(2) . ?
N4 C9 1.381(2) . ?
N4 H4 0.8600 . ?
O1 C13 1.263(2) . ?
O2 C13 1.251(2) . ?
O3 C27 1.275(2) . ?
O3 Co1 2.0812(13) 1_454 ?
O4 C27 1.236(2) . ?
O4 Co1 2.3513(16) 1_454 ?
O5 C20 1.215(3) . ?
O1W H1WA 0.8497 . ?
O1W H1WB 0.8525 . ?
C1 H1 0.9300 . ?
C2 C3 1.363(3) . ?
C2 H2 0.9300 . ?
C3 C5 1.467(3) . ?
C4 C5 1.377(3) . ?
C4 C6 1.386(3) 3_665 ?
C4 H4A 0.9300 . ?
C5 C6 1.382(3) . ?
C6 C4 1.386(3) 3_665 ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.365(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.463(3) . ?
C10 C12 1.381(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.385(3) 3_567 ?
C11 H11 0.9300 . ?
C12 C11 1.385(3) 3_567 ?
C12 H12 0.9300 . ?
C13 C14 1.502(3) . ?
C14 C15 1.383(3) . ?
C14 C19 1.389(3) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(3) . ?
C17 C20 1.503(3) . ?
C18 C19 1.378(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.495(3) . ?
C21 C26 1.387(3) . ?
C21 C22 1.393(3) . ?
C22 C23 1.380(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.387(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.392(3) . ?
C24 C27 1.501(3) . ?
C25 C26 1.377(3) . ?
C25 H25 0.9300 . ?
C26 H26 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
N3 Co1 N1 102.84(7) . . ?
N3 Co1 O1 138.17(6) . . ?
N1 Co1 O1 99.78(6) . . ?
N3 Co1 O3 102.37(6) . 1_656 ?
N1 Co1 O3 94.13(6) . 1_656 ?
O1 Co1 O3 110.61(5) . 1_656 ?
N3 Co1 O2 86.75(6) . . ?
N1 Co1 O2 89.56(6) . . ?
O1 Co1 O2 58.60(5) . . ?
O3 Co1 O2 169.10(5) 1_656 . ?
N3 Co1 O4 92.55(6) . 1_656 ?
N1 Co1 O4 151.23(6) . 1_656 ?
O1 Co1 O4 83.73(6) . 1_656 ?
O3 Co1 O4 58.51(5) 1_656 1_656 ?
O2 Co1 O4 115.77(5) . 1_656 ?
C1 N1 C2 105.05(16) . . ?
C1 N1 Co1 126.24(13) . . ?
C2 N1 Co1 127.22(13) . . ?
C1 N2 C3 108.14(16) . . ?
C1 N2 H2A 125.9 . . ?
C3 N2 H2A 125.9 . . ?
C7 N3 C8 105.49(15) . . ?
C7 N3 Co1 121.97(13) . . ?
C8 N3 Co1 131.02(13) . . ?
C7 N4 C9 108.27(15) . . ?
C7 N4 H4 125.9 . . ?
C9 N4 H4 125.9 . . ?
C13 O1 Co1 96.73(12) . . ?
C13 O2 Co1 85.20(11) . . ?
C27 O3 Co1 96.18(11) . 1_454 ?
C27 O4 Co1 84.79(12) . 1_454 ?
H1WA O1W H1WB 99.7 . . ?
N1 C1 N2 111.51(17) . . ?
N1 C1 H1 124.2 . . ?
N2 C1 H1 124.2 . . ?
C3 C2 N1 110.25(17) . . ?
C3 C2 H2 124.9 . . ?
N1 C2 H2 124.9 . . ?
C2 C3 N2 105.05(16) . . ?
C2 C3 C5 131.56(18) . . ?
N2 C3 C5 123.37(17) . . ?
C5 C4 C6 121.4(2) . 3_665 ?
C5 C4 H4A 119.3 . . ?
C6 C4 H4A 119.3 3_665 . ?
C4 C5 C6 117.44(19) . . ?
C4 C5 C3 120.56(18) . . ?
C6 C5 C3 121.99(19) . . ?
C5 C6 C4 121.2(2) . 3_665 ?
C5 C6 H6 119.4 . . ?
C4 C6 H6 119.4 3_665 . ?
N3 C7 N4 111.36(17) . . ?
N3 C7 H7 124.3 . . ?
N4 C7 H7 124.3 . . ?
C9 C8 N3 109.88(16) . . ?
C9 C8 H8 125.1 . . ?
N3 C8 H8 125.1 . . ?
C8 C9 N4 104.99(16) . . ?
C8 C9 C10 132.13(18) . . ?
N4 C9 C10 122.88(17) . . ?
C12 C10 C11 117.68(19) . . ?
C12 C10 C9 120.60(18) . . ?
C11 C10 C9 121.72(18) . . ?
C10 C11 C12 121.1(2) . 3_567 ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 3_567 . ?
C10 C12 C11 121.2(2) . 3_567 ?
C10 C12 H12 119.4 . . ?
C11 C12 H12 119.4 3_567 . ?
O2 C13 O1 119.45(17) . . ?
O2 C13 C14 120.44(17) . . ?
O1 C13 C14 120.11(17) . . ?
C15 C14 C19 119.50(18) . . ?
C15 C14 C13 120.83(17) . . ?
C19 C14 C13 119.67(17) . . ?
C14 C15 C16 120.50(19) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 119.96(19) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 119.32(19) . . ?
C18 C17 C20 120.87(19) . . ?
C16 C17 C20 119.63(19) . . ?
C19 C18 C17 120.58(19) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 120.11(19) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
O5 C20 C21 121.29(19) . . ?
O5 C20 C17 120.97(19) . . ?
C21 C20 C17 117.70(18) . . ?
C26 C21 C22 119.20(19) . . ?
C26 C21 C20 121.88(19) . . ?
C22 C21 C20 118.91(19) . . ?
C23 C22 C21 120.24(19) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.21(19) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C25 119.62(18) . . ?
C23 C24 C27 119.92(17) . . ?
C25 C24 C27 120.45(17) . . ?
C26 C25 C24 119.95(19) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 120.66(19) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
O4 C27 O3 120.32(18) . . ?
O4 C27 C24 121.02(18) . . ?
O3 C27 C24 118.66(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
C2 N1 C1 N2 -0.3(2) . . . . ?
Co1 N1 C1 N2 166.57(13) . . . . ?
C3 N2 C1 N1 -0.1(2) . . . . ?
C1 N1 C2 C3 0.5(2) . . . . ?
Co1 N1 C2 C3 -166.17(14) . . . . ?
N1 C2 C3 N2 -0.5(2) . . . . ?
N1 C2 C3 C5 -179.0(2) . . . . ?
C1 N2 C3 C2 0.4(2) . . . . ?
C1 N2 C3 C5 178.99(19) . . . . ?
C6 C4 C5 C6 -0.3(5) 3_665 . . . ?
C6 C4 C5 C3 179.0(3) 3_665 . . . ?
C2 C3 C5 C4 -9.8(4) . . . . ?
N2 C3 C5 C4 172.0(2) . . . . ?
C2 C3 C5 C6 169.4(3) . . . . ?
N2 C3 C5 C6 -8.8(3) . . . . ?
C4 C5 C6 C4 0.3(5) . . . 3_665 ?
C3 C5 C6 C4 -179.0(3) . . . 3_665 ?
C8 N3 C7 N4 -0.8(2) . . . . ?
Co1 N3 C7 N4 166.55(13) . . . . ?
C9 N4 C7 N3 0.5(2) . . . . ?
C7 N3 C8 C9 0.9(2) . . . . ?
Co1 N3 C8 C9 -164.89(14) . . . . ?
N3 C8 C9 N4 -0.6(2) . . . . ?
N3 C8 C9 C10 178.7(2) . . . . ?
C7 N4 C9 C8 0.1(2) . . . . ?
C7 N4 C9 C10 -179.32(19) . . . . ?
C8 C9 C10 C12 19.4(4) . . . . ?
N4 C9 C10 C12 -161.3(2) . . . . ?
C8 C9 C10 C11 -160.0(3) . . . . ?
N4 C9 C10 C11 19.2(3) . . . . ?
C12 C10 C11 C12 -0.1(5) . . . 3_567 ?
C9 C10 C11 C12 179.4(3) . . . 3_567 ?
C11 C10 C12 C11 0.1(5) . . . 3_567 ?
C9 C10 C12 C11 -179.4(3) . . . 3_567 ?
Co1 O2 C13 O1 -1.19(18) . . . . ?
Co1 O2 C13 C14 178.28(17) . . . . ?
Co1 O1 C13 O2 1.3(2) . . . . ?
Co1 O1 C13 C14 -178.13(15) . . . . ?
O2 C13 C14 C15 -175.7(2) . . . . ?
O1 C13 C14 C15 3.8(3) . . . . ?
O2 C13 C14 C19 4.2(3) . . . . ?
O1 C13 C14 C19 -176.3(2) . . . . ?
C19 C14 C15 C16 0.0(3) . . . . ?
C13 C14 C15 C16 179.9(2) . . . . ?
C14 C15 C16 C17 1.3(4) . . . . ?
C15 C16 C17 C18 -1.3(4) . . . . ?
C15 C16 C17 C20 -176.6(2) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C20 C17 C18 C19 175.3(2) . . . . ?
C17 C18 C19 C14 1.1(4) . . . . ?
C15 C14 C19 C18 -1.2(4) . . . . ?
C13 C14 C19 C18 178.9(2) . . . . ?
C18 C17 C20 O5 -150.3(2) . . . . ?
C16 C17 C20 O5 24.9(3) . . . . ?
C18 C17 C20 C21 27.5(3) . . . . ?
C16 C17 C20 C21 -157.4(2) . . . . ?
O5 C20 C21 C26 -139.8(2) . . . . ?
C17 C20 C21 C26 42.4(3) . . . . ?
O5 C20 C21 C22 40.9(3) . . . . ?
C17 C20 C21 C22 -136.9(2) . . . . ?
C26 C21 C22 C23 -2.7(3) . . . . ?
C20 C21 C22 C23 176.6(2) . . . . ?
C21 C22 C23 C24 2.7(4) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
C22 C23 C24 C27 -179.0(2) . . . . ?
C23 C24 C25 C26 -2.7(3) . . . . ?
C27 C24 C25 C26 176.35(19) . . . . ?
C24 C25 C26 C21 2.7(3) . . . . ?
C22 C21 C26 C25 0.0(3) . . . . ?
C20 C21 C26 C25 -179.3(2) . . . . ?
Co1 O4 C27 O3 4.30(18) 1_454 . . . ?
Co1 O4 C27 C24 -175.26(17) 1_454 . . . ?
Co1 O3 C27 O4 -4.9(2) 1_454 . . . ?
Co1 O3 C27 C24 174.70(14) 1_454 . . . ?
C23 C24 C27 O4 2.0(3) . . . . ?
C25 C24 C27 O4 -177.1(2) . . . . ?
C23 C24 C27 O3 -177.61(18) . . . . ?
C25 C24 C27 O3 3.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WB O1 0.85 2.57 3.094(3) 120.5 .
O1W H1WA O4 0.85 2.23 3.018(3) 154.3 1_656
N4 H4 O2 0.86 1.93 2.775(2) 166.6 3_566
N2 H2A O3 0.86 1.98 2.785(2) 155.3 3_565
N2 H2A O3 0.86 1.98 2.785(2) 155.3 3_565
N4 H4 O2 0.86 1.93 2.775(2) 166.6 3_566
O1W H1WA O4 0.85 2.23 3.018(3) 154.3 1_656
O1W H1WB O1 0.85 2.57 3.094(3) 120.5 .
N2 H2A O3 0.86 1.98 2.785(2) 155.3 3_565
N4 H4 O2 0.86 1.93 2.775(2) 166.6 3_566
O1W H1WA O4 0.85 2.23 3.018(3) 154.3 1_656
O1W H1WB O1 0.85 2.57 3.094(3) 120.5 .

_refine_diff_density_max         0.436
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1549988'
_audit_update_record             
;
2017-09-13 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H13 Cd N2 O6'
_chemical_formula_weight         501.73

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   9.2381(7)
_cell_length_b                   10.1167(8)
_cell_length_c                   11.7020(8)
_cell_angle_alpha                82.635(2)
_cell_angle_beta                 71.861(2)
_cell_angle_gamma                63.266(2)
_cell_volume                     928.12(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4846
_cell_measurement_theta_min      2.2543
_cell_measurement_theta_max      27.4229

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_F_000             498
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.220
_shelx_estimated_absorpt_T_min   0.742
_shelx_estimated_absorpt_T_max   0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5939
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3982
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.254
_diffrn_reflns_theta_max         24.243
_diffrn_reflns_theta_full        24.243
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             2873
_reflns_number_gt                2805
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0848P)²+4.4195P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2873
_refine_ls_number_parameters     271
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.061
_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_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
Cd1 Cd 0.66358(4) 0.81056(4) 0.40947(3) 0.0110(2) Uani 1 1 d . . . . .
N1 N 0.9409(6) 0.7102(5) 0.3302(4) 0.0151(10) Uani 1 1 d . . . . .
N2 N 1.2063(6) 0.5715(5) 0.3217(4) 0.0165(10) Uani 1 1 d . . . . .
H2 H 1.2950 0.5182 0.3450 0.020 Uiso 1 1 calc R U . . .
O1 O 0.4310(5) 0.7794(5) 0.4515(3) 0.0164(8) Uani 1 1 d . . . . .
O2 O 0.5367(5) 0.6007(5) 0.5748(4) 0.0220(9) Uani 1 1 d . . . . .
O3 O -0.5450(5) 0.9528(4) 0.6383(4) 0.0174(9) Uani 1 1 d . . . . .
O4 O -0.2768(5) 0.7878(5) 0.5868(4) 0.0250(10) Uani 1 1 d . . . . .
O5 O -0.5920(5) 0.7937(4) 1.2366(3) 0.0157(8) Uani 1 1 d . . . . .
H5 H -0.5877 0.7749 1.3205 0.024 Uiso 1 1 d R U . . .
O6 O -0.3230(5) 0.7507(5) 1.2039(3) 0.0169(9) Uani 1 1 d . . . . .
C1 C 0.4153(7) 0.6927(6) 0.5415(5) 0.0129(11) Uani 1 1 d . . . . .
C2 C 0.2388(7) 0.7178(6) 0.6098(5) 0.0134(11) Uani 1 1 d . . . . .
C3 C 0.1012(8) 0.8532(6) 0.6065(5) 0.0178(12) Uani 1 1 d . . . . .
H3 H 0.1184 0.9276 0.5570 0.021 Uiso 1 1 calc R U . . .
C4 C -0.0604(7) 0.8782(6) 0.6757(5) 0.0167(12) Uani 1 1 d . . . . .
H4 H -0.1501 0.9702 0.6740 0.020 Uiso 1 1 calc R U . . .
C5 C -0.0909(7) 0.7663(6) 0.7486(5) 0.0140(11) Uani 1 1 d . U . . .
C6 C 0.0477(7) 0.6297(6) 0.7503(5) 0.0151(11) Uani 1 1 d . . . . .
H6 H 0.0304 0.5541 0.7978 0.018 Uiso 1 1 calc R U . . .
C7 C 0.2084(7) 0.6060(6) 0.6830(5) 0.0131(11) Uani 1 1 d . . . . .
H7 H 0.2986 0.5146 0.6857 0.016 Uiso 1 1 calc R U . . .
C8 C -0.2610(7) 0.7951(6) 0.8312(5) 0.0121(11) Uani 1 1 d . . . . .
C9 C -0.4117(7) 0.8496(6) 0.7930(5) 0.0099(10) Uani 1 1 d . . . . .
C10 C -0.4103(7) 0.8665(6) 0.6630(5) 0.0149(12) Uani 1 1 d . . . . .
C11 C -0.5663(7) 0.8826(6) 0.8785(5) 0.0112(11) Uani 1 1 d . U . . .
H11 H -0.6638 0.9218 0.8537 0.013 Uiso 1 1 calc R U . . .
C12 C -0.5801(7) 0.8588(6) 1.0004(5) 0.0102(10) Uani 1 1 d . . . . .
H12 H -0.6850 0.8802 1.0562 0.012 Uiso 1 1 calc R U . . .
C13 C -0.4344(7) 0.8025(6) 1.0375(5) 0.0111(11) Uani 1 1 d . . . . .
C14 C -0.2774(7) 0.7733(6) 0.9527(5) 0.0116(11) Uani 1 1 d . . . . .
H14 H -0.1816 0.7382 0.9791 0.014 Uiso 1 1 calc R U . . .
C15 C -0.4437(6) 0.7797(5) 1.1666(5) 0.0091(10) Uani 1 1 d . U . . .
C16 C 1.0372(7) 0.6881(6) 0.2109(5) 0.0162(12) Uani 1 1 d . . . . .
H16 H 0.9948 0.7269 0.1455 0.019 Uiso 1 1 calc R U . . .
C17 C 1.0482(7) 0.6394(7) 0.3943(5) 0.0172(12) Uani 1 1 d . . . . .
H17 H 1.0183 0.6368 0.4778 0.021 Uiso 1 1 calc R U . . .
C18 C 1.2036(7) 0.6010(6) 0.2035(5) 0.0106(11) Uani 1 1 d . . . . .
C19 C 1.3560(7) 0.5465(5) 0.1009(5) 0.0103(10) Uani 1 1 d . . . . .
C20 C 1.5173(7) 0.4737(6) 0.1137(5) 0.0136(11) Uani 1 1 d . . . . .
H20 H 1.5303 0.4545 0.1907 0.016 Uiso 1 1 calc R U . . .
C21 C 1.6588(7) 0.4290(6) 0.0168(5) 0.0138(11) Uani 1 1 d . U . . .
H21 H 1.7654 0.3820 0.0289 0.017 Uiso 1 1 calc R U . . .


_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
Cd1 O1 2.207(4) . ?
Cd1 N1 2.208(5) . ?
Cd1 O3 2.219(4) 2_576 ?
Cd1 O4 2.266(4) 1_655 ?
Cd1 O6 2.507(4) 1_654 ?
N1 C17 1.321(7) . ?
N1 C16 1.384(7) . ?
N2 C17 1.342(8) . ?
N2 C18 1.383(7) . ?
N2 H2 0.8600 . ?
O1 C1 1.297(7) . ?
O2 C1 1.231(7) . ?
O3 C10 1.255(7) . ?
O3 Cd1 2.219(4) 2_576 ?
O4 C10 1.251(7) . ?
O4 Cd1 2.266(4) 1_455 ?
O5 C15 1.313(7) . ?
O5 H5 0.9859 . ?
O6 C15 1.224(7) . ?
O6 Cd1 2.507(4) 1_456 ?
C1 C2 1.492(8) . ?
C2 C3 1.395(8) . ?
C2 C7 1.407(8) . ?
C3 C4 1.381(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.407(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(8) . ?
C5 C8 1.484(8) . ?
C6 C7 1.372(8) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C14 1.382(8) . ?
C8 C9 1.441(8) . ?
C9 C11 1.385(8) . ?
C9 C10 1.506(7) . ?
C11 C12 1.391(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.402(8) . ?
C13 C15 1.480(7) . ?
C14 H14 0.9300 . ?
C16 C18 1.365(8) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.465(8) . ?
C19 C20 1.382(8) . ?
C19 C21 1.406(8) 2_865 ?
C20 C21 1.370(8) . ?
C20 H20 0.9300 . ?
C21 C19 1.406(8) 2_865 ?
C21 H21 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
O1 Cd1 N1 145.95(16) . . ?
O1 Cd1 O3 95.32(15) . 2_576 ?
N1 Cd1 O3 111.55(17) . 2_576 ?
O1 Cd1 O4 105.62(15) . 1_655 ?
N1 Cd1 O4 84.78(16) . 1_655 ?
O3 Cd1 O4 110.48(15) 2_576 1_655 ?
O1 Cd1 O6 79.65(13) . 1_654 ?
N1 Cd1 O6 81.27(15) . 1_654 ?
O3 Cd1 O6 86.95(14) 2_576 1_654 ?
O4 Cd1 O6 160.85(16) 1_655 1_654 ?
C17 N1 C16 106.1(5) . . ?
C17 N1 Cd1 123.1(4) . . ?
C16 N1 Cd1 130.2(4) . . ?
C17 N2 C18 109.0(5) . . ?
C17 N2 H2 125.5 . . ?
C18 N2 H2 125.5 . . ?
C1 O1 Cd1 113.7(3) . . ?
C10 O3 Cd1 136.2(4) . 2_576 ?
C10 O4 Cd1 107.6(4) . 1_455 ?
C15 O5 H5 109.5 . . ?
C15 O6 Cd1 126.3(3) . 1_456 ?
O2 C1 O1 122.7(5) . . ?
O2 C1 C2 120.9(5) . . ?
O1 C1 C2 116.2(5) . . ?
C3 C2 C7 118.3(5) . . ?
C3 C2 C1 121.3(5) . . ?
C7 C2 C1 120.3(5) . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.8(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.1(5) . . ?
C6 C5 C8 120.2(5) . . ?
C4 C5 C8 121.5(5) . . ?
C7 C6 C5 121.0(5) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 120.9(5) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
C14 C8 C9 117.7(5) . . ?
C14 C8 C5 118.2(5) . . ?
C9 C8 C5 124.0(5) . . ?
C11 C9 C8 119.4(5) . . ?
C11 C9 C10 117.2(5) . . ?
C8 C9 C10 123.3(5) . . ?
O4 C10 O3 124.0(5) . . ?
O4 C10 C9 117.7(5) . . ?
O3 C10 C9 118.2(5) . . ?
C9 C11 C12 122.0(5) . . ?
C9 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C11 C12 C13 118.9(5) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C13 C14 120.0(5) . . ?
C12 C13 C15 120.7(5) . . ?
C14 C13 C15 119.2(5) . . ?
C8 C14 C13 122.0(5) . . ?
C8 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
O6 C15 O5 123.4(5) . . ?
O6 C15 C13 122.4(5) . . ?
O5 C15 C13 114.2(4) . . ?
C18 C16 N1 110.0(5) . . ?
C18 C16 H16 125.0 . . ?
N1 C16 H16 125.0 . . ?
N1 C17 N2 110.4(5) . . ?
N1 C17 H17 124.8 . . ?
N2 C17 H17 124.8 . . ?
C16 C18 N2 104.5(5) . . ?
C16 C18 C19 132.2(5) . . ?
N2 C18 C19 123.2(5) . . ?
C20 C19 C21 117.3(5) . 2_865 ?
C20 C19 C18 122.9(5) . . ?
C21 C19 C18 119.7(5) 2_865 . ?
C21 C20 C19 122.2(5) . . ?
C21 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
C20 C21 C19 120.5(5) . 2_865 ?
C20 C21 H21 119.7 . . ?
C19 C21 H21 119.7 2_865 . ?

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
Cd1 O1 C1 O2 -22.2(7) . . . . ?
Cd1 O1 C1 C2 153.2(4) . . . . ?
O2 C1 C2 C3 153.8(6) . . . . ?
O1 C1 C2 C3 -21.7(8) . . . . ?
O2 C1 C2 C7 -23.9(8) . . . . ?
O1 C1 C2 C7 160.6(5) . . . . ?
C7 C2 C3 C4 1.7(9) . . . . ?
C1 C2 C3 C4 -176.0(5) . . . . ?
C2 C3 C4 C5 -1.9(9) . . . . ?
C3 C4 C5 C6 1.0(9) . . . . ?
C3 C4 C5 C8 174.8(5) . . . . ?
C4 C5 C6 C7 0.1(8) . . . . ?
C8 C5 C6 C7 -173.8(5) . . . . ?
C5 C6 C7 C2 -0.3(8) . . . . ?
C3 C2 C7 C6 -0.6(8) . . . . ?
C1 C2 C7 C6 177.1(5) . . . . ?
C6 C5 C8 C14 53.4(7) . . . . ?
C4 C5 C8 C14 -120.3(6) . . . . ?
C6 C5 C8 C9 -128.9(6) . . . . ?
C4 C5 C8 C9 57.5(8) . . . . ?
C14 C8 C9 C11 2.2(7) . . . . ?
C5 C8 C9 C11 -175.5(5) . . . . ?
C14 C8 C9 C10 -174.8(5) . . . . ?
C5 C8 C9 C10 7.4(8) . . . . ?
Cd1 O4 C10 O3 -6.9(7) 1_455 . . . ?
Cd1 O4 C10 C9 169.4(4) 1_455 . . . ?
Cd1 O3 C10 O4 -91.7(7) 2_576 . . . ?
Cd1 O3 C10 C9 92.1(6) 2_576 . . . ?
C11 C9 C10 O4 -152.9(5) . . . . ?
C8 C9 C10 O4 24.2(8) . . . . ?
C11 C9 C10 O3 23.6(7) . . . . ?
C8 C9 C10 O3 -159.3(5) . . . . ?
C8 C9 C11 C12 -2.8(8) . . . . ?
C10 C9 C11 C12 174.4(5) . . . . ?
C9 C11 C12 C13 1.1(8) . . . . ?
C11 C12 C13 C14 1.2(8) . . . . ?
C11 C12 C13 C15 178.2(5) . . . . ?
C9 C8 C14 C13 0.0(8) . . . . ?
C5 C8 C14 C13 177.9(5) . . . . ?
C12 C13 C14 C8 -1.7(8) . . . . ?
C15 C13 C14 C8 -178.8(5) . . . . ?
Cd1 O6 C15 O5 -27.3(7) 1_456 . . . ?
Cd1 O6 C15 C13 152.5(4) 1_456 . . . ?
C12 C13 C15 O6 -169.4(5) . . . . ?
C14 C13 C15 O6 7.7(8) . . . . ?
C12 C13 C15 O5 10.4(7) . . . . ?
C14 C13 C15 O5 -172.5(4) . . . . ?
C17 N1 C16 C18 1.0(7) . . . . ?
Cd1 N1 C16 C18 -170.3(4) . . . . ?
C16 N1 C17 N2 -1.2(7) . . . . ?
Cd1 N1 C17 N2 170.9(4) . . . . ?
C18 N2 C17 N1 0.9(7) . . . . ?
N1 C16 C18 N2 -0.5(6) . . . . ?
N1 C16 C18 C19 -179.1(5) . . . . ?
C17 N2 C18 C16 -0.3(6) . . . . ?
C17 N2 C18 C19 178.5(5) . . . . ?
C16 C18 C19 C20 171.6(6) . . . . ?
N2 C18 C19 C20 -6.8(8) . . . . ?
C16 C18 C19 C21 -6.9(9) . . . 2_865 ?
N2 C18 C19 C21 174.8(5) . . . 2_865 ?
C21 C19 C20 C21 1.3(9) 2_865 . . . ?
C18 C19 C20 C21 -177.2(5) . . . . ?
C19 C20 C21 C19 -1.3(9) . . . 2_865 ?

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
C17 H17 O4 0.93 2.45 2.991(7) 117.5 1_655
N2 H2 O2 0.86 1.92 2.768(6) 169.3 2_766
C17 H17 O4 0.93 2.45 2.991(7) 117.5 1_655
O5 H5 O1 0.99 1.60 2.570(5) 165.3 1_456
N2 H2 O2 0.86 1.92 2.768(6) 169.3 2_766
C17 H17 O4 0.93 2.45 2.991(7) 117.5 1_655
O5 H5 O1 0.99 1.60 2.570(5) 165.3 1_456
N2 H2 O2 0.86 1.92 2.768(6) 169.3 2_766
C17 H17 O4 0.93 2.45 2.991(7) 117.5 1_655
O5 H5 O1 0.99 1.60 2.570(5) 165.3 1_456
N2 H2 O2 0.86 1.92 2.768(6) 169.3 2_766
N2 H2 O2 0.86 1.92 2.768(6) 169.3 2_766
O5 H5 O1 0.99 1.60 2.570(5) 165.3 1_456
C17 H17 O4 0.93 2.45 2.991(7) 117.5 1_655
N2 H2 O2 0.86 1.92 2.768(6) 169.3 2_766
O5 H5 O1 0.99 1.60 2.570(5) 165.3 1_456
C17 H17 O4 0.93 2.45 2.991(7) 117.5 1_655
N2 H2 O2 0.86 1.92 2.768(6) 169.3 2_766
O5 H5 O1 0.99 1.60 2.570(5) 165.3 1_456
C17 H17 O4 0.93 2.45 2.991(7) 117.5 1_655

_refine_diff_density_max         1.486
_refine_diff_density_min         -1.009
_refine_diff_density_rms         0.181

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1549985'
_audit_update_record             
;
2017-09-13 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H18 N4 O5 Zn'
_chemical_formula_weight         543.82

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

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

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

_cell_length_a                   11.0779(11)
_cell_length_b                   22.030(2)
_cell_length_c                   11.4217(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2787.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3389
_cell_measurement_theta_min      2.5613
_cell_measurement_theta_max      27.2841

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.922
_shelx_estimated_absorpt_T_min   0.809
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4367
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15068
_diffrn_reflns_av_unetI/netI     0.1032
_diffrn_reflns_av_R_equivalents  0.1133
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.008
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3211
_reflns_number_gt                2136
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0915P)²+5.6379P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3211
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.1872
_refine_ls_wR_factor_gt          0.1655
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.003

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
Zn1 Zn 0.21522(6) 0.2500 0.2500 0.0271(2) Uani 1 2 d S T P . .
N1 N 0.3195(3) 0.30175(16) 0.1468(3) 0.0333(8) Uani 1 1 d . . . . .
N2 N 0.4290(4) 0.33052(17) -0.0039(3) 0.0421(10) Uani 1 1 d . . . . .
H2 H 0.4693 0.3285 -0.0681 0.051 Uiso 1 1 calc R U . . .
O1 O 0.1514(3) 0.19120(13) 0.1256(2) 0.0333(7) Uani 1 1 d . . . . .
O2 O 0.0421(3) 0.18382(14) 0.2861(2) 0.0367(7) Uani 1 1 d . . . . .
O3 O -0.2500 0.0000 -0.1659(4) 0.0567(16) Uani 1 2 d S T P . .
C1 C 0.3415(4) 0.3633(2) 0.1546(3) 0.0327(10) Uani 1 1 d . . . . .
H1 H 0.3139 0.3883 0.2146 0.039 Uiso 1 1 calc R U . . .
C2 C 0.3741(5) 0.2843(2) 0.0497(4) 0.0465(13) Uani 1 1 d . . . . .
H2A H 0.3744 0.2446 0.0220 0.056 Uiso 1 1 calc R U . . .
C3 C 0.4096(4) 0.3824(2) 0.0619(3) 0.0325(10) Uani 1 1 d . . . . .
C4 C 0.4574(4) 0.4420(2) 0.0294(3) 0.0311(9) Uani 1 1 d . . . . .
C5 C 0.4200(4) 0.4930(2) 0.0904(4) 0.0407(11) Uani 1 1 d . . . . .
H5 H 0.3658 0.4887 0.1520 0.049 Uiso 1 1 calc R U . . .
C6 C 0.5387(5) 0.4504(2) -0.0614(4) 0.0425(11) Uani 1 1 d . . . . .
H6 H 0.5657 0.4169 -0.1035 0.051 Uiso 1 1 calc R U . . .
C7 C 0.0623(4) 0.16991(19) 0.1811(3) 0.0298(9) Uani 1 1 d . . . . .
C8 C -0.0202(4) 0.12626(19) 0.1193(3) 0.0288(9) Uani 1 1 d . . . . .
C9 C 0.0055(4) 0.1065(2) 0.0063(3) 0.0315(9) Uani 1 1 d . . . . .
H9 H 0.0739 0.1209 -0.0319 0.038 Uiso 1 1 calc R U . . .
C10 C -0.0692(4) 0.0657(2) -0.0494(3) 0.0308(9) Uani 1 1 d . . . . .
H10 H -0.0511 0.0528 -0.1248 0.037 Uiso 1 1 calc R U . . .
C11 C -0.1720(4) 0.0438(2) 0.0069(3) 0.0320(9) Uani 1 1 d . . . . .
C12 C -0.1998(4) 0.0657(2) 0.1178(4) 0.0384(11) Uani 1 1 d . . . . .
H12 H -0.2701 0.0528 0.1547 0.046 Uiso 1 1 calc R U . . .
C13 C -0.1250(4) 0.1061(2) 0.1735(3) 0.0366(11) Uani 1 1 d . . . . .
H13 H -0.1446 0.1200 0.2480 0.044 Uiso 1 1 calc R U . . .
C14 C -0.2500 0.0000 -0.0586(5) 0.0374(16) Uani 1 2 d S T P . .


_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 N1 2.006(3) . ?
Zn1 N1 2.006(3) 3 ?
Zn1 O1 2.048(3) 3 ?
Zn1 O1 2.048(3) . ?
Zn1 O2 2.444(3) . ?
Zn1 O2 2.444(3) 3 ?
Zn1 C7 2.569(4) 3 ?
N1 C2 1.321(5) . ?
N1 C1 1.381(5) . ?
N2 C2 1.334(6) . ?
N2 C3 1.384(5) . ?
N2 H2 0.8600 . ?
O1 C7 1.263(5) . ?
O2 C7 1.257(5) . ?
O3 C14 1.225(7) . ?
C1 C3 1.366(5) . ?
C1 H1 0.9300 . ?
C2 H2A 0.9300 . ?
C3 C4 1.464(6) . ?
C4 C6 1.386(5) . ?
C4 C5 1.385(6) . ?
C5 C6 1.369(6) 5_665 ?
C5 H5 0.9300 . ?
C6 C5 1.369(6) 5_665 ?
C6 H6 0.9300 . ?
C7 C8 1.504(6) . ?
C8 C13 1.389(5) . ?
C8 C9 1.391(5) . ?
C9 C10 1.377(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(6) . ?
C11 C14 1.496(5) . ?
C12 C13 1.373(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C11 1.496(5) 2_455 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Zn1 N1 109.7(2) . 3 ?
N1 Zn1 O1 104.30(13) . 3 ?
N1 Zn1 O1 98.66(12) 3 3 ?
N1 Zn1 O1 98.66(12) . . ?
N1 Zn1 O1 104.30(13) 3 . ?
O1 Zn1 O1 139.62(16) 3 . ?
N1 Zn1 O2 152.86(12) . . ?
N1 Zn1 O2 90.79(13) 3 . ?
O1 Zn1 O2 89.40(11) 3 . ?
O1 Zn1 O2 57.91(10) . . ?
N1 Zn1 O2 90.79(13) . 3 ?
N1 Zn1 O2 152.86(12) 3 3 ?
O1 Zn1 O2 57.91(10) 3 3 ?
O1 Zn1 O2 89.40(11) . 3 ?
O2 Zn1 O2 76.61(15) . 3 ?
N1 Zn1 C7 99.75(14) . 3 ?
N1 Zn1 C7 126.16(13) 3 3 ?
O1 Zn1 C7 29.06(11) 3 3 ?
O1 Zn1 C7 114.77(13) . 3 ?
O2 Zn1 C7 80.83(12) . 3 ?
O2 Zn1 C7 28.90(11) 3 3 ?
C2 N1 C1 105.0(3) . . ?
C2 N1 Zn1 126.3(3) . . ?
C1 N1 Zn1 128.4(3) . . ?
C2 N2 C3 108.1(3) . . ?
C2 N2 H2 126.0 . . ?
C3 N2 H2 126.0 . . ?
C7 O1 Zn1 99.0(2) . . ?
C7 O2 Zn1 81.1(2) . . ?
C3 C1 N1 110.4(4) . . ?
C3 C1 H1 124.8 . . ?
N1 C1 H1 124.8 . . ?
N1 C2 N2 111.8(4) . . ?
N1 C2 H2A 124.1 . . ?
N2 C2 H2A 124.1 . . ?
C1 C3 N2 104.6(4) . . ?
C1 C3 C4 132.3(4) . . ?
N2 C3 C4 123.1(3) . . ?
C6 C4 C5 117.5(4) . . ?
C6 C4 C3 123.0(4) . . ?
C5 C4 C3 119.4(4) . . ?
C6 C5 C4 121.1(4) 5_665 . ?
C6 C5 H5 119.4 5_665 . ?
C4 C5 H5 119.4 . . ?
C5 C6 C4 121.3(4) 5_665 . ?
C5 C6 H6 119.3 5_665 . ?
C4 C6 H6 119.3 . . ?
O2 C7 O1 121.8(4) . . ?
O2 C7 C8 119.7(4) . . ?
O1 C7 C8 118.5(3) . . ?
C13 C8 C9 119.0(4) . . ?
C13 C8 C7 120.2(4) . . ?
C9 C8 C7 120.8(3) . . ?
C10 C9 C8 120.6(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.3(4) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 118.8(4) . . ?
C10 C11 C14 117.7(4) . . ?
C12 C11 C14 123.5(4) . . ?
C13 C12 C11 120.9(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C8 120.3(4) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
O3 C14 C11 120.0(2) . 2_455 ?
O3 C14 C11 120.0(2) . . ?
C11 C14 C11 119.9(5) 2_455 . ?

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
C2 N1 C1 C3 -0.1(5) . . . . ?
Zn1 N1 C1 C3 -174.9(3) . . . . ?
C1 N1 C2 N2 0.1(6) . . . . ?
Zn1 N1 C2 N2 175.0(3) . . . . ?
C3 N2 C2 N1 0.0(6) . . . . ?
N1 C1 C3 N2 0.1(5) . . . . ?
N1 C1 C3 C4 -179.7(4) . . . . ?
C2 N2 C3 C1 0.0(5) . . . . ?
C2 N2 C3 C4 179.7(4) . . . . ?
C1 C3 C4 C6 171.2(5) . . . . ?
N2 C3 C4 C6 -8.5(7) . . . . ?
C1 C3 C4 C5 -9.5(8) . . . . ?
N2 C3 C4 C5 170.9(4) . . . . ?
C6 C4 C5 C6 0.4(8) . . . 5_665 ?
C3 C4 C5 C6 -179.0(4) . . . 5_665 ?
C5 C4 C6 C5 -0.4(8) . . . 5_665 ?
C3 C4 C6 C5 179.0(5) . . . 5_665 ?
Zn1 O2 C7 O1 4.1(4) . . . . ?
Zn1 O2 C7 C8 -176.6(4) . . . . ?
Zn1 O1 C7 O2 -4.9(5) . . . . ?
Zn1 O1 C7 C8 175.8(3) . . . . ?
O2 C7 C8 C13 6.5(6) . . . . ?
O1 C7 C8 C13 -174.2(4) . . . . ?
O2 C7 C8 C9 -174.9(4) . . . . ?
O1 C7 C8 C9 4.4(6) . . . . ?
C13 C8 C9 C10 -2.4(7) . . . . ?
C7 C8 C9 C10 178.9(4) . . . . ?
C8 C9 C10 C11 0.1(7) . . . . ?
C9 C10 C11 C12 2.6(7) . . . . ?
C9 C10 C11 C14 179.6(4) . . . . ?
C10 C11 C12 C13 -2.9(7) . . . . ?
C14 C11 C12 C13 -179.7(4) . . . . ?
C11 C12 C13 C8 0.6(8) . . . . ?
C9 C8 C13 C12 2.1(7) . . . . ?
C7 C8 C13 C12 -179.2(4) . . . . ?
C10 C11 C14 O3 -25.3(4) . . . . ?
C12 C11 C14 O3 151.6(4) . . . . ?
C10 C11 C14 C11 154.7(4) . . . 2_455 ?
C12 C11 C14 C11 -28.4(4) . . . 2_455 ?

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
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665
N2 H2 O2 0.86 1.87 2.725(4) 172.4 8_665

_refine_diff_density_max         0.959
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.092


