# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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. 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 1887626'
_audit_update_record             
;
2018-12-26 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;
_audit_creation_date             2018-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 N4 Ni O4, H2 O'
_chemical_formula_sum            'C22 H20 N4 Ni O5'
_chemical_formula_weight         479.13
_chemical_absolute_configuration ad
_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'
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'

_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   18.5939(8)
_cell_length_b                   7.6992(3)
_cell_length_c                   14.9541(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2140.80(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6223
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.475
_cell_measurement_theta_min      2.579
_shelx_estimated_absorpt_T_max   0.797
_shelx_estimated_absorpt_T_min   0.770
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0553 before and 0.0449 after correction. The Ratio of minimum to maximum transmission is 0.8689. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11295
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.580
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_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         0.795
_reflns_Friedel_fraction_full    0.869
_reflns_Friedel_fraction_max     0.859
_reflns_number_gt                3794
_reflns_number_total             4077
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SIR2004 (Burla et al.,  2007)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.042(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4077
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0226
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0170P)²+0.2439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0525
_refine_ls_wR_factor_ref         0.0536
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.958(14)
 0.042(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
3.a Free rotating group:
 O5(H5A,H5B)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Ni1 Ni 0.77534(2) 0.67839(4) 0.40229(3) 0.04630(10) Uani 1 1 d . . . . .
O1 O 0.37197(8) 0.9656(2) 0.39058(14) 0.0528(5) Uani 1 1 d . . . . .
O2 O 0.28621(11) 0.9974(3) 0.29264(16) 0.0686(6) Uani 1 1 d . . . . .
O3 O 0.78975(10) 0.8966(3) 0.31811(16) 0.0631(6) Uani 1 1 d . . . . .
O4 O 0.68347(9) 0.8341(2) 0.37166(14) 0.0585(6) Uani 1 1 d . . . . .
N1 N 0.72134(12) 0.5072(3) 0.48202(18) 0.0550(6) Uani 1 1 d . . . . .
N2 N 0.63798(11) 0.4165(3) 0.57536(16) 0.0502(5) Uani 1 1 d . . . . .
N3 N 0.38206(11) 0.5372(3) 0.59815(14) 0.0426(5) Uani 1 1 d . . . . .
N4 N 0.30861(12) 0.6776(3) 0.50778(17) 0.0496(5) Uani 1 1 d . . . . .
C1 C 0.34667(14) 1.0409(4) 0.3228(2) 0.0531(7) Uani 1 1 d . . . . .
C2 C 0.38651(16) 1.1888(5) 0.2782(3) 0.0751(10) Uani 1 1 d . . . . .
H2A H 0.373987 1.296281 0.308281 0.090 Uiso 1 1 calc R . . . .
H2B H 0.370292 1.197965 0.216758 0.090 Uiso 1 1 calc R . . . .
C3 C 0.46781(15) 1.1696(4) 0.2786(2) 0.0556(7) Uani 1 1 d . . . . .
C4 C 0.50819(18) 1.2162(4) 0.3516(2) 0.0654(8) Uani 1 1 d . . . . .
H4 H 0.485795 1.263888 0.401499 0.078 Uiso 1 1 calc R . . . .
C5 C 0.58237(18) 1.1927(4) 0.3515(3) 0.0689(9) Uani 1 1 d . . . . .
H5 H 0.608910 1.226304 0.401272 0.083 Uiso 1 1 calc R . . . .
C6 C 0.61702(15) 1.1215(4) 0.2800(3) 0.0608(8) Uani 1 1 d . . . . .
C7 C 0.57684(18) 1.0790(4) 0.2059(2) 0.0667(9) Uani 1 1 d . . . . .
H7 H 0.599443 1.033411 0.155604 0.080 Uiso 1 1 calc R . . . .
C8 C 0.50289(18) 1.1035(4) 0.2055(2) 0.0657(9) Uani 1 1 d . . . . .
H8 H 0.476642 1.074626 0.154696 0.079 Uiso 1 1 calc R . . . .
C9 C 0.69731(16) 1.0938(5) 0.2806(3) 0.0830(12) Uani 1 1 d . . . . .
H9A H 0.713942 1.092551 0.219089 0.100 Uiso 1 1 calc R . . . .
H9B H 0.719472 1.192819 0.309698 0.100 Uiso 1 1 calc R . . . .
C10 C 0.72396(13) 0.9313(4) 0.3257(2) 0.0565(7) Uani 1 1 d . . . . .
C11 C 0.65632(14) 0.5344(4) 0.5128(2) 0.0531(7) Uani 1 1 d . . . . .
H11 H 0.626484 0.623983 0.493707 0.064 Uiso 1 1 calc R . . . .
C12 C 0.69533(18) 0.3061(5) 0.5836(3) 0.0715(10) Uani 1 1 d . . . . .
H12 H 0.698622 0.210135 0.621180 0.086 Uiso 1 1 calc R . . . .
C13 C 0.74590(17) 0.3640(4) 0.5268(3) 0.0693(9) Uani 1 1 d . . . . .
H13 H 0.791003 0.313994 0.519027 0.083 Uiso 1 1 calc R . . . .
C14 C 0.57210(14) 0.4083(3) 0.62416(18) 0.0467(6) Uani 1 1 d . . . . .
C15 C 0.50963(14) 0.4723(3) 0.58657(17) 0.0424(6) Uani 1 1 d . . . . .
H15 H 0.509953 0.517909 0.528985 0.051 Uiso 1 1 calc R . . . .
C16 C 0.44679(13) 0.4678(3) 0.63548(17) 0.0422(6) Uani 1 1 d . . . . .
C17 C 0.44553(18) 0.3971(4) 0.7202(2) 0.0616(8) Uani 1 1 d . . . . .
H17 H 0.402833 0.392182 0.752536 0.074 Uiso 1 1 calc R . . . .
C18 C 0.5081(2) 0.3341(5) 0.7561(2) 0.0750(10) Uani 1 1 d . . . . .
H18 H 0.507477 0.286907 0.813389 0.090 Uiso 1 1 calc R . . . .
C19 C 0.57152(19) 0.3389(4) 0.7098(2) 0.0630(8) Uani 1 1 d . . . . .
H19 H 0.613591 0.296246 0.735324 0.076 Uiso 1 1 calc R . . . .
C20 C 0.37558(14) 0.6286(4) 0.52171(19) 0.0518(7) Uani 1 1 d . . . . .
H20 H 0.413647 0.654021 0.483546 0.062 Uiso 1 1 calc R . . . .
C21 C 0.27165(15) 0.6163(5) 0.5795(2) 0.0614(8) Uani 1 1 d . . . . .
H21 H 0.222581 0.631891 0.588515 0.074 Uiso 1 1 calc R . . . .
C22 C 0.31477(16) 0.5313(4) 0.6350(2) 0.0610(8) Uani 1 1 d . . . . .
H22 H 0.301792 0.478124 0.688460 0.073 Uiso 1 1 calc R . . . .
O5 O 0.5343(2) 0.8415(4) 0.4584(2) 0.0980(9) Uani 1 1 d . . . . .
H5A H 0.571911 0.885528 0.435343 0.147 Uiso 1 1 d G . . . .
H5B H 0.499729 0.913341 0.454210 0.147 Uiso 1 1 d G . . . .


_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 O1 2.1186(16) 3_565 ?
Ni1 O2 2.136(2) 3_565 ?
Ni1 O3 2.116(2) . ?
Ni1 O4 2.1366(18) . ?
Ni1 N1 2.041(2) . ?
Ni1 N4 2.025(3) 3_565 ?
Ni1 C1 2.454(3) 3_565 ?
Ni1 C10 2.453(3) . ?
O1 C1 1.259(3) . ?
O2 C1 1.257(3) . ?
O3 C10 1.257(3) . ?
O4 C10 1.265(3) . ?
N1 C11 1.310(3) . ?
N1 C13 1.368(4) . ?
N2 C11 1.348(3) . ?
N2 C12 1.369(4) . ?
N2 C14 1.427(3) . ?
N3 C16 1.430(3) . ?
N3 C20 1.348(4) . ?
N3 C22 1.368(3) . ?
N4 C20 1.318(3) . ?
N4 C21 1.359(4) . ?
C1 C2 1.513(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.519(4) . ?
C3 C4 1.372(5) . ?
C3 C8 1.371(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.363(5) . ?
C6 C7 1.376(5) . ?
C6 C9 1.508(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(5) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.506(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.344(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(4) . ?
C14 C19 1.388(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(4) . ?
C16 C17 1.380(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.370(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.368(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.327(5) . ?
C22 H22 0.9300 . ?
O5 H5A 0.8499 . ?
O5 H5B 0.8500 . ?

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 Ni1 O2 61.61(7) 3_565 3_565 ?
O1 Ni1 O4 162.55(8) 3_565 . ?
O1 Ni1 C1 30.85(8) 3_565 3_565 ?
O1 Ni1 C10 135.01(9) 3_565 . ?
O2 Ni1 O4 105.46(8) 3_565 . ?
O2 Ni1 C1 30.80(8) 3_565 3_565 ?
O2 Ni1 C10 100.46(11) 3_565 . ?
O3 Ni1 O1 105.01(8) . 3_565 ?
O3 Ni1 O2 91.97(10) . 3_565 ?
O3 Ni1 O4 61.86(7) . . ?
O3 Ni1 C1 100.94(10) . 3_565 ?
O3 Ni1 C10 30.83(8) . . ?
O4 Ni1 C1 135.59(9) . 3_565 ?
O4 Ni1 C10 31.03(8) . . ?
N1 Ni1 O1 97.32(8) . 3_565 ?
N1 Ni1 O2 94.92(10) . 3_565 ?
N1 Ni1 O3 157.26(8) . . ?
N1 Ni1 O4 95.41(8) . . ?
N1 Ni1 C1 95.99(10) . 3_565 ?
N1 Ni1 C10 126.43(9) . . ?
N4 Ni1 O1 95.27(8) 3_565 3_565 ?
N4 Ni1 O2 156.37(8) 3_565 3_565 ?
N4 Ni1 O3 89.43(10) 3_565 . ?
N4 Ni1 O4 95.98(9) 3_565 . ?
N4 Ni1 N1 92.80(10) 3_565 . ?
N4 Ni1 C1 126.07(9) 3_565 3_565 ?
N4 Ni1 C10 92.75(11) 3_565 . ?
C10 Ni1 C1 122.05(11) . 3_565 ?
C1 O1 Ni1 89.47(15) . 3_465 ?
C1 O2 Ni1 88.74(18) . 3_465 ?
C10 O3 Ni1 89.53(18) . . ?
C10 O4 Ni1 88.42(15) . . ?
C11 N1 Ni1 123.74(19) . . ?
C11 N1 C13 105.4(2) . . ?
C13 N1 Ni1 129.9(2) . . ?
C11 N2 C12 106.5(2) . . ?
C11 N2 C14 127.0(2) . . ?
C12 N2 C14 126.5(2) . . ?
C20 N3 C16 127.0(2) . . ?
C20 N3 C22 106.1(2) . . ?
C22 N3 C16 126.9(2) . . ?
C20 N4 Ni1 124.66(19) . 3_465 ?
C20 N4 C21 104.7(2) . . ?
C21 N4 Ni1 130.6(2) . 3_465 ?
O1 C1 Ni1 59.68(14) . 3_465 ?
O1 C1 C2 121.2(2) . . ?
O2 C1 Ni1 60.47(16) . 3_465 ?
O2 C1 O1 120.0(3) . . ?
O2 C1 C2 118.7(3) . . ?
C2 C1 Ni1 174.7(2) . 3_465 ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C1 C2 C3 114.4(2) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C4 C3 C2 121.5(3) . . ?
C8 C3 C2 120.4(3) . . ?
C8 C3 C4 118.1(3) . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.5(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 118.1(3) . . ?
C5 C6 C9 121.4(3) . . ?
C7 C6 C9 120.5(4) . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 121.2(3) . . ?
C3 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C6 C9 H9A 108.2 . . ?
C6 C9 H9B 108.2 . . ?
H9A C9 H9B 107.3 . . ?
C10 C9 C6 116.5(2) . . ?
C10 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
O3 C10 Ni1 59.64(16) . . ?
O3 C10 O4 120.2(3) . . ?
O3 C10 C9 117.2(3) . . ?
O4 C10 Ni1 60.55(14) . . ?
O4 C10 C9 122.6(2) . . ?
C9 C10 Ni1 175.8(2) . . ?
N1 C11 N2 111.7(2) . . ?
N1 C11 H11 124.2 . . ?
N2 C11 H11 124.2 . . ?
N2 C12 H12 126.8 . . ?
C13 C12 N2 106.4(3) . . ?
C13 C12 H12 126.8 . . ?
N1 C13 H13 125.0 . . ?
C12 C13 N1 110.1(3) . . ?
C12 C13 H13 125.0 . . ?
C15 C14 N2 119.9(2) . . ?
C15 C14 C19 120.4(3) . . ?
C19 C14 N2 119.7(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.2(2) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 N3 119.8(2) . . ?
C15 C16 C17 120.8(3) . . ?
C17 C16 N3 119.5(2) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 119.0(3) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.6(3) . . ?
C19 C18 H18 119.2 . . ?
C14 C19 H19 120.5 . . ?
C18 C19 C14 119.0(3) . . ?
C18 C19 H19 120.5 . . ?
N3 C20 H20 124.2 . . ?
N4 C20 N3 111.6(2) . . ?
N4 C20 H20 124.2 . . ?
N4 C21 H21 124.5 . . ?
C22 C21 N4 111.1(2) . . ?
C22 C21 H21 124.5 . . ?
N3 C22 H22 126.7 . . ?
C21 C22 N3 106.5(3) . . ?
C21 C22 H22 126.7 . . ?
H5A O5 H5B 109.5 . . ?

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
Ni1 O1 C1 O2 -3.8(3) 3_465 . . . ?
Ni1 O1 C1 C2 173.9(3) 3_465 . . . ?
Ni1 O2 C1 O1 3.8(3) 3_465 . . . ?
Ni1 O2 C1 C2 -174.0(3) 3_465 . . . ?
Ni1 O3 C10 O4 -1.3(3) . . . . ?
Ni1 O3 C10 C9 176.9(3) . . . . ?
Ni1 O4 C10 O3 1.3(3) . . . . ?
Ni1 O4 C10 C9 -176.8(4) . . . . ?
Ni1 N1 C11 N2 -169.50(19) . . . . ?
Ni1 N1 C13 C12 169.2(3) . . . . ?
Ni1 N4 C20 N3 178.70(17) 3_465 . . . ?
Ni1 N4 C21 C22 -178.1(2) 3_465 . . . ?
O1 C1 C2 C3 35.6(5) . . . . ?
O2 C1 C2 C3 -146.7(3) . . . . ?
N2 C12 C13 N1 -0.8(5) . . . . ?
N2 C14 C15 C16 -178.3(2) . . . . ?
N2 C14 C19 C18 179.2(3) . . . . ?
N3 C16 C17 C18 -178.7(3) . . . . ?
N4 C21 C22 N3 -0.1(4) . . . . ?
C1 C2 C3 C4 -82.5(4) . . . . ?
C1 C2 C3 C8 97.0(4) . . . . ?
C2 C3 C4 C5 178.1(3) . . . . ?
C2 C3 C8 C7 -177.6(3) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C4 C3 C8 C7 2.0(5) . . . . ?
C4 C5 C6 C7 2.4(5) . . . . ?
C4 C5 C6 C9 -179.1(3) . . . . ?
C5 C6 C7 C8 -1.9(5) . . . . ?
C5 C6 C9 C10 82.9(5) . . . . ?
C6 C7 C8 C3 -0.3(5) . . . . ?
C6 C9 C10 O3 172.3(4) . . . . ?
C6 C9 C10 O4 -9.5(6) . . . . ?
C7 C6 C9 C10 -98.6(4) . . . . ?
C8 C3 C4 C5 -1.5(5) . . . . ?
C9 C6 C7 C8 179.6(3) . . . . ?
C11 N1 C13 C12 0.3(4) . . . . ?
C11 N2 C12 C13 0.9(4) . . . . ?
C11 N2 C14 C15 28.3(4) . . . . ?
C11 N2 C14 C19 -150.6(3) . . . . ?
C12 N2 C11 N1 -0.8(4) . . . . ?
C12 N2 C14 C15 -152.3(3) . . . . ?
C12 N2 C14 C19 28.9(4) . . . . ?
C13 N1 C11 N2 0.3(4) . . . . ?
C14 N2 C11 N1 178.8(3) . . . . ?
C14 N2 C12 C13 -178.6(3) . . . . ?
C14 C15 C16 N3 178.6(2) . . . . ?
C14 C15 C16 C17 -1.4(4) . . . . ?
C15 C14 C19 C18 0.3(5) . . . . ?
C15 C16 C17 C18 1.3(5) . . . . ?
C16 N3 C20 N4 -178.2(2) . . . . ?
C16 N3 C22 C21 177.8(3) . . . . ?
C16 C17 C18 C19 -0.4(5) . . . . ?
C17 C18 C19 C14 -0.4(5) . . . . ?
C19 C14 C15 C16 0.6(4) . . . . ?
C20 N3 C16 C15 -8.5(4) . . . . ?
C20 N3 C16 C17 171.5(3) . . . . ?
C20 N3 C22 C21 0.7(3) . . . . ?
C20 N4 C21 C22 -0.5(4) . . . . ?
C21 N4 C20 N3 1.0(3) . . . . ?
C22 N3 C16 C15 174.9(3) . . . . ?
C22 N3 C16 C17 -5.1(4) . . . . ?
C22 N3 C20 N4 -1.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.958(14)
2 0.042(14)

####################################################################### 
# 
# 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_yd0933_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1966122'
loop_
_audit_author_name
_audit_author_address
CCDAS
;YANANUnversity
China
;
_audit_update_record             
;
2019-11-16 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H26 Co N4 O8'
_chemical_formula_weight         533.40

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      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                   5.5521(17)
_cell_length_b                   10.630(3)
_cell_length_c                   10.978(3)
_cell_angle_alpha                66.111(4)
_cell_angle_beta                 87.833(5)
_cell_angle_gamma                80.289(5)
_cell_volume                     583.6(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             277
_exptl_transmission_factor_min   0.7011
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.791
_shelx_estimated_absorpt_T_min   0.839
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3189
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0104
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.030
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2271
_reflns_number_gt                2104
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2271
_refine_ls_number_parameters     168
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1391
_refine_ls_wR_factor_gt          0.1226
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_restrained_S_all      1.209
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 1.000000 0.500000 0.500000 0.0216(2) Uani 1 2 d S . P . .
O1 O 0.7113(3) 0.5026(2) 0.37791(19) 0.0318(4) Uani 1 1 d D . . . .
H1B H 0.789(5) 0.478(3) 0.321(3) 0.051(10) Uiso 1 1 d D . . . .
H1A H 0.594(4) 0.459(3) 0.404(3) 0.051(10) Uiso 1 1 d D . . . .
O2 O 0.7346(3) 0.59280(18) 0.59899(17) 0.0277(4) Uani 1 1 d . . . . .
O3 O 0.9662(4) 0.5965(3) 0.7565(3) 0.0608(7) Uani 1 1 d . . . . .
O4 O 1.0968(8) 0.6612(4) 0.9734(4) 0.1277(16) Uani 1 1 d . . . . .
H4B H 1.160218 0.686453 0.897286 0.153 Uiso 1 1 d R U . . .
H4C H 1.021207 0.595623 0.979996 0.153 Uiso 1 1 d R U . . .
N1 N 0.9666(4) 0.2992(2) 0.6413(2) 0.0286(5) Uani 1 1 d . . . . .
N2 N 0.8231(4) 0.1316(2) 0.8060(2) 0.0269(5) Uani 1 1 d . . . . .
C1 C 0.7709(5) 0.6298(3) 0.6914(3) 0.0304(6) Uani 1 1 d . . . . .
C2 C 0.5616(5) 0.7254(3) 0.7200(3) 0.0397(7) Uani 1 1 d . . . . .
H2A H 0.412789 0.686030 0.730997 0.048 Uiso 1 1 calc R U . . .
H2AB H 0.597813 0.733072 0.802205 0.048 Uiso 1 1 calc R U . . .
C3 C 0.5244(5) 0.8682(3) 0.6072(3) 0.0342(6) Uani 1 1 d . . . . .
C4 C 0.3341(5) 0.9133(3) 0.5140(3) 0.0392(7) Uani 1 1 d . . . . .
H4 H 0.220466 0.855466 0.522595 0.047 Uiso 1 1 calc R U . . .
C5 C 0.3089(5) 1.0410(3) 0.4095(3) 0.0384(6) Uani 1 1 d . . . . .
H5 H 0.178913 1.068190 0.348258 0.046 Uiso 1 1 calc R U . . .
C6 C 0.7840(5) 0.2671(3) 0.7208(3) 0.0319(6) Uani 1 1 d . . . . .
H6 H 0.644399 0.330217 0.718746 0.038 Uiso 1 1 calc R U . . .
C7 C 1.1323(5) 0.1772(3) 0.6761(3) 0.0294(5) Uani 1 1 d . . . . .
H7 H 1.280931 0.167714 0.636037 0.035 Uiso 1 1 calc R U . . .
C8 C 1.0462(5) 0.0733(3) 0.7771(3) 0.0288(5) Uani 1 1 d . . . . .
H8 H 1.122629 -0.019125 0.818824 0.035 Uiso 1 1 calc R U . . .
C9 C 0.6595(5) 0.0645(3) 0.9054(2) 0.0272(5) Uani 1 1 d . . . . .
C10 C 0.4947(5) 0.1419(3) 0.9556(3) 0.0329(6) Uani 1 1 d . . . . .
H10 H 0.491902 0.237413 0.925961 0.039 Uiso 1 1 calc R U . . .
C11 C 0.6674(5) -0.0772(3) 0.9494(3) 0.0323(6) Uani 1 1 d . . . . .
H11 H 0.780301 -0.129193 0.915848 0.039 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
Co1 N1 2.104(2) 2_766 ?
Co1 N1 2.104(2) . ?
Co1 O1 2.1176(19) . ?
Co1 O1 2.1176(19) 2_766 ?
Co1 O2 2.1405(17) . ?
Co1 O2 2.1406(17) 2_766 ?
O1 H1B 0.848(10) . ?
O1 H1A 0.839(10) . ?
O2 C1 1.262(3) . ?
O3 C1 1.239(3) . ?
O4 H4B 0.8501 . ?
O4 H4C 0.8500 . ?
N1 C6 1.309(3) . ?
N1 C7 1.377(3) . ?
N2 C6 1.348(3) . ?
N2 C8 1.375(3) . ?
N2 C9 1.427(3) . ?
C1 C2 1.521(4) . ?
C2 C3 1.507(4) . ?
C2 H2A 0.9700 . ?
C2 H2AB 0.9700 . ?
C3 C4 1.381(4) . ?
C3 C5 1.403(4) 2_676 ?
C4 C5 1.365(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.350(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.376(4) . ?
C9 C11 1.377(3) . ?
C10 C11 1.388(3) 2_657 ?
C10 H10 0.9300 . ?
C11 H11 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
N1 Co1 N1 180.0 2_766 . ?
N1 Co1 O1 87.76(8) 2_766 . ?
N1 Co1 O1 92.24(8) . . ?
N1 Co1 O1 92.24(8) 2_766 2_766 ?
N1 Co1 O1 87.76(8) . 2_766 ?
O1 Co1 O1 180.0 . 2_766 ?
N1 Co1 O2 89.23(8) 2_766 . ?
N1 Co1 O2 90.77(8) . . ?
O1 Co1 O2 88.17(7) . . ?
O1 Co1 O2 91.83(7) 2_766 . ?
N1 Co1 O2 90.77(8) 2_766 2_766 ?
N1 Co1 O2 89.23(8) . 2_766 ?
O1 Co1 O2 91.83(7) . 2_766 ?
O1 Co1 O2 88.17(7) 2_766 2_766 ?
O2 Co1 O2 180.0 . 2_766 ?
Co1 O1 H1B 102(2) . . ?
Co1 O1 H1A 126(2) . . ?
H1B O1 H1A 109.2(16) . . ?
C1 O2 Co1 127.95(16) . . ?
H4B O4 H4C 105.9 . . ?
C6 N1 C7 105.6(2) . . ?
C6 N1 Co1 125.78(18) . . ?
C7 N1 Co1 128.55(18) . . ?
C6 N2 C8 106.7(2) . . ?
C6 N2 C9 125.4(2) . . ?
C8 N2 C9 127.8(2) . . ?
O3 C1 O2 124.2(2) . . ?
O3 C1 C2 118.9(2) . . ?
O2 C1 C2 116.8(2) . . ?
C3 C2 C1 110.3(2) . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2AB 109.6 . . ?
C1 C2 H2AB 109.6 . . ?
H2A C2 H2AB 108.1 . . ?
C4 C3 C5 117.3(3) . 2_676 ?
C4 C3 C2 122.4(3) . . ?
C5 C3 C2 120.3(3) 2_676 . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C3 121.2(3) . 2_676 ?
C4 C5 H5 119.4 . . ?
C3 C5 H5 119.4 2_676 . ?
N1 C6 N2 111.8(2) . . ?
N1 C6 H6 124.1 . . ?
N2 C6 H6 124.1 . . ?
C8 C7 N1 109.7(2) . . ?
C8 C7 H7 125.1 . . ?
N1 C7 H7 125.1 . . ?
C7 C8 N2 106.2(2) . . ?
C7 C8 H8 126.9 . . ?
N2 C8 H8 126.9 . . ?
C10 C9 C11 120.6(2) . . ?
C10 C9 N2 119.9(2) . . ?
C11 C9 N2 119.5(2) . . ?
C9 C10 C11 119.9(2) . 2_657 ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 2_657 . ?
C9 C11 C10 119.4(3) . 2_657 ?
C9 C11 H11 120.3 . . ?
C10 C11 H11 120.3 2_657 . ?

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 O2 C1 O3 -12.9(4) . . . . ?
Co1 O2 C1 C2 164.97(17) . . . . ?
O3 C1 C2 C3 108.3(3) . . . . ?
O2 C1 C2 C3 -69.7(3) . . . . ?
C1 C2 C3 C4 104.0(3) . . . . ?
C1 C2 C3 C5 -73.5(3) . . . 2_676 ?
C5 C3 C4 C5 0.2(4) 2_676 . . . ?
C2 C3 C4 C5 -177.4(2) . . . . ?
C3 C4 C5 C3 -0.2(5) . . . 2_676 ?
C7 N1 C6 N2 0.6(3) . . . . ?
Co1 N1 C6 N2 -175.93(17) . . . . ?
C8 N2 C6 N1 -0.7(3) . . . . ?
C9 N2 C6 N1 179.7(2) . . . . ?
C6 N1 C7 C8 -0.3(3) . . . . ?
Co1 N1 C7 C8 176.08(17) . . . . ?
N1 C7 C8 N2 -0.1(3) . . . . ?
C6 N2 C8 C7 0.4(3) . . . . ?
C9 N2 C8 C7 -180.0(2) . . . . ?
C6 N2 C9 C10 -24.8(4) . . . . ?
C8 N2 C9 C10 155.6(3) . . . . ?
C6 N2 C9 C11 154.8(3) . . . . ?
C8 N2 C9 C11 -24.8(4) . . . . ?
C11 C9 C10 C11 -0.7(5) . . . 2_657 ?
N2 C9 C10 C11 178.9(2) . . . 2_657 ?
C10 C9 C11 C10 0.7(4) . . . 2_657 ?
N2 C9 C11 C10 -178.9(2) . . . 2_657 ?

_refine_diff_density_max         0.493
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.139



####################################################################### 
# 
# 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_yd0686_0m
_database_code_depnum_ccdc_archive 'CCDC 1887653'
loop_
_audit_author_name
_audit_author_address
CCDCA
;YAN An Unversity
China
;
_audit_update_record             
;
2018-12-28 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;
_audit_creation_date             2018-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C78 H72 N16 Ni3 O16, 2(H2 O)'
_chemical_formula_sum            'C78 H76 N16 Ni3 O18'
_chemical_formula_weight         1701.67
_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'
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'

_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                   11.0003(6)
_cell_length_b                   12.7408(7)
_cell_length_c                   15.3439(8)
_cell_angle_alpha                103.4100(10)
_cell_angle_beta                 108.6770(10)
_cell_angle_gamma                95.7550(10)
_cell_volume                     1945.82(18)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8142
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      30.672
_cell_measurement_theta_min      2.345
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0434 before and 0.0212 after correction. The Ratio of minimum to maximum transmission is 0.8385. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0106
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.793
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12865
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.793
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.837
_diffrn_reflns_theta_min         2.634
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.793
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8515
_reflns_number_total             9695
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.184
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         9695
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.221
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+2.3386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1408
_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 O(H,H) groups
2. Restrained distances
 C13-C14 = C9-C10 = C11-C12
 1.4 with sigma of 0.02
3. Others
 Fixed Sof: O5(0.5) O10(0.5) C8(0.5) H8C(0.5) H8D(0.5) C9(0.5) C14(0.5)
 H14(0.5) C13(0.5) H13(0.5) C12(0.5) H12(0.5) C11(0.5) H11(0.5) C10(0.5)
 C43(0.5) H43A(0.5) H43B(0.5) C45(0.5) C46(0.5)
4.a Free rotating group:
 O9(H9A,H9B)
4.b Rotating group:
 O6(H6A,H6B), O8(H8A,H8B)
4.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C8(H8C,H8D), C43(H43A,H43B)
4.d Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C12(H12), C11(H11), C15(H15), C17(H17), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C29(H29), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36),
 C37(H37), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Ni1 Ni 0.000000 0.000000 1.000000 0.03017(12) Uani 1 2 d S T P . .
Ni2 Ni 0.42406(3) 0.31693(3) 0.73398(2) 0.03138(10) Uani 1 1 d . . . . .
O1 O 0.0524(2) 0.05425(17) 0.89772(14) 0.0408(5) Uani 1 1 d . . . . .
O2 O -0.0853(3) -0.0696(3) 0.76624(17) 0.0723(9) Uani 1 1 d . . . . .
O3 O 0.3796(2) 0.20289(18) 0.79974(14) 0.0427(5) Uani 1 1 d . . . . .
O4 O 0.4589(2) 0.42116(17) 0.65546(15) 0.0416(5) Uani 1 1 d . . . . .
O5 O 0.3845(7) 0.4281(5) 0.2717(5) 0.0741(18) Uani 0.5 1 d . . . A 1
O10 O 0.5537(10) 0.5713(5) 0.7679(4) 0.108(3) Uani 0.5 1 d . . . B 2
O6 O 0.4728(3) 0.4439(2) 0.86396(18) 0.0563(6) Uani 1 1 d . . . . .
H6A H 0.544074 0.489008 0.874356 0.085 Uiso 1 1 d GR . . . .
H6B H 0.493352 0.416638 0.912486 0.085 Uiso 1 1 d GR . . . .
O7 O 0.4523(2) 0.2911(2) 0.95556(16) 0.0506(6) Uani 1 1 d . . . . .
O8 O -0.1870(2) -0.07687(18) 0.90092(15) 0.0440(5) Uani 1 1 d . . . . .
H8A H -0.208044 -0.141436 0.906565 0.066 Uiso 1 1 d GR . . . .
H8B H -0.186463 -0.089857 0.843285 0.066 Uiso 1 1 d GR . . . .
N1 N 0.6149(2) 0.2922(2) 0.77640(17) 0.0359(5) Uani 1 1 d . . . . .
N2 N 0.8301(2) 0.33484(18) 0.83106(16) 0.0321(5) Uani 1 1 d . . . . .
N3 N 1.1139(2) 0.69229(19) 0.93306(17) 0.0348(5) Uani 1 1 d . . . . .
N4 N 1.0777(2) 0.86138(19) 0.96604(17) 0.0352(5) Uani 1 1 d . . . . .
N5 N 0.2361(2) 0.3507(2) 0.69971(19) 0.0413(6) Uani 1 1 d . . . . .
N6 N 0.0212(2) 0.3223(2) 0.64281(18) 0.0380(5) Uani 1 1 d . . . . .
N7 N -0.2922(2) -0.02151(19) 0.49113(16) 0.0350(5) Uani 1 1 d . . . . .
N8 N -0.3610(2) -0.18713(19) 0.39080(16) 0.0333(5) Uani 1 1 d . . . . .
C1 C 0.0146(3) 0.0037(3) 0.8109(2) 0.0415(7) Uani 1 1 d . . . . .
C2 C 0.0999(3) 0.0331(3) 0.7548(2) 0.0457(7) Uani 1 1 d . . . . .
H2A H 0.044620 0.022990 0.688801 0.055 Uiso 1 1 calc R . . . .
H2B H 0.141304 0.110009 0.781910 0.055 Uiso 1 1 calc R . . . .
C3 C 0.2042(3) -0.0357(3) 0.7564(2) 0.0439(7) Uani 1 1 d . . . . .
C4 C 0.3290(3) -0.0038(3) 0.8258(2) 0.0430(7) Uani 1 1 d . . . . .
C5 C 0.3675(3) 0.0993(3) 0.9082(2) 0.0449(7) Uani 1 1 d . . . . .
H5A H 0.441376 0.091319 0.959862 0.054 Uiso 1 1 calc R . . . .
H5B H 0.295471 0.105464 0.931483 0.054 Uiso 1 1 calc R . . . .
C6 C 0.4036(3) 0.2063(3) 0.8858(2) 0.0354(6) Uani 1 1 d . . . . .
C8 C 0.5069(10) 0.5806(9) 0.6078(7) 0.046(2) Uani 0.5 1 d . . . A -1
H8C H 0.435796 0.545390 0.547559 0.055 Uiso 0.5 1 calc R . . A -1
H8D H 0.494794 0.654982 0.630876 0.055 Uiso 0.5 1 calc R . . A -1
C9 C 0.6347(6) 0.5841(5) 0.5915(4) 0.0388(12) Uani 0.5 1 d D . . A -1
C14 C 0.7554(9) 0.6589(6) 0.6659(5) 0.060(2) Uani 0.5 1 d D . . A -1
H14 H 0.745418 0.703921 0.719334 0.072 Uiso 0.5 1 calc R . . A -1
C13 C 0.8610(7) 0.6662(6) 0.6633(7) 0.065(2) Uani 0.5 1 d D . . A -1
H13 H 0.932108 0.709262 0.715594 0.078 Uiso 0.5 1 calc R . . A -1
C12 C 0.8799(7) 0.6024(7) 0.5705(7) 0.066(2) Uani 0.5 1 d D . . A -1
H12 H 0.960093 0.612715 0.562386 0.079 Uiso 0.5 1 calc R . . A -1
C11 C 0.7780(8) 0.5334(6) 0.5042(5) 0.0531(18) Uani 0.5 1 d D . . A -1
H11 H 0.789721 0.490711 0.450498 0.064 Uiso 0.5 1 calc R . . A -1
C10 C 0.6492(6) 0.5199(4) 0.5093(4) 0.0381(12) Uani 0.5 1 d D . . A -1
C15 C 0.7158(3) 0.3711(2) 0.8035(2) 0.0346(6) Uani 1 1 d . . . . .
H15 H 0.710005 0.443531 0.803811 0.041 Uiso 1 1 calc R . . . .
C16 C 0.9576(3) 0.3998(2) 0.86690(18) 0.0313(5) Uani 1 1 d . . . . .
C17 C 0.9727(3) 0.5126(2) 0.8795(2) 0.0337(6) Uani 1 1 d . . . . .
H17 H 0.899830 0.545001 0.862083 0.040 Uiso 1 1 calc R . . . .
C18 C 1.0970(3) 0.5761(2) 0.91817(19) 0.0325(5) Uani 1 1 d . . . . .
C19 C 1.0281(3) 0.7570(2) 0.9474(2) 0.0334(5) Uani 1 1 d . . . . .
H19 H 0.944359 0.730983 0.944455 0.040 Uiso 1 1 calc R . . . .
C20 C 1.2015(3) 0.8633(3) 0.9632(2) 0.0436(7) Uani 1 1 d . . . . .
H20 H 1.260170 0.926777 0.973724 0.052 Uiso 1 1 calc R . . . .
C21 C 1.2264(3) 0.7611(3) 0.9433(3) 0.0465(7) Uani 1 1 d . . . . .
H21 H 1.303026 0.740849 0.937636 0.056 Uiso 1 1 calc R . . . .
C22 C 1.2067(3) 0.5288(3) 0.9429(2) 0.0438(7) Uani 1 1 d . . . . .
H22 H 1.290060 0.571987 0.969146 0.053 Uiso 1 1 calc R . . . .
C23 C 1.1897(3) 0.4163(3) 0.9279(3) 0.0490(8) Uani 1 1 d . . . . .
H23 H 1.262882 0.383872 0.943414 0.059 Uiso 1 1 calc R . . . .
C24 C 1.0663(3) 0.3504(3) 0.8902(2) 0.0418(7) Uani 1 1 d . . . . .
H24 H 1.056524 0.274765 0.880606 0.050 Uiso 1 1 calc R . . . .
C25 C 0.7967(3) 0.2235(3) 0.8205(3) 0.0461(7) Uani 1 1 d . . . . .
H25 H 0.853537 0.175194 0.833632 0.055 Uiso 1 1 calc R . . . .
C26 C 0.6649(3) 0.1996(3) 0.7872(2) 0.0467(7) Uani 1 1 d . . . . .
H26 H 0.615200 0.130363 0.773605 0.056 Uiso 1 1 calc R . . . .
C27 C 0.1293(3) 0.2766(3) 0.6618(2) 0.0405(6) Uani 1 1 d . . . . .
H27 H 0.127448 0.201351 0.649330 0.049 Uiso 1 1 calc R . . . .
C28 C -0.1114(3) 0.2646(2) 0.6029(2) 0.0354(6) Uani 1 1 d . . . . .
C29 C -0.1382(3) 0.1514(2) 0.5651(2) 0.0367(6) Uani 1 1 d . . . . .
H29 H -0.070580 0.112937 0.565254 0.044 Uiso 1 1 calc R . . . .
C30 C -0.2669(3) 0.0961(2) 0.52712(19) 0.0356(6) Uani 1 1 d . . . . .
C31 C -0.3502(3) -0.0810(2) 0.39890(19) 0.0349(6) Uani 1 1 d . . . . .
H31 H -0.378827 -0.051255 0.347676 0.042 Uiso 1 1 calc R . . . .
C32 C -0.3061(3) -0.1957(3) 0.4823(2) 0.0389(6) Uani 1 1 d . . . . .
H32 H -0.299975 -0.261456 0.498437 0.047 Uiso 1 1 calc R . . . .
C33 C -0.2625(3) -0.0949(3) 0.5454(2) 0.0426(7) Uani 1 1 d . . . . .
H33 H -0.221053 -0.078118 0.611455 0.051 Uiso 1 1 calc R . . . .
C34 C -0.3686(3) 0.1512(3) 0.5251(2) 0.0429(7) Uani 1 1 d . . . . .
H34 H -0.454564 0.113102 0.499130 0.051 Uiso 1 1 calc R . . . .
C35 C -0.3407(3) 0.2641(3) 0.5624(2) 0.0457(7) Uani 1 1 d . . . . .
H35 H -0.408677 0.302334 0.561187 0.055 Uiso 1 1 calc R . . . .
C36 C -0.2125(3) 0.3213(3) 0.6016(2) 0.0411(6) Uani 1 1 d . . . . .
H36 H -0.194702 0.397310 0.626728 0.049 Uiso 1 1 calc R . . . .
C37 C 0.0647(3) 0.4343(3) 0.6738(3) 0.0516(8) Uani 1 1 d . . . . .
H37 H 0.013603 0.488211 0.671717 0.062 Uiso 1 1 calc R . . . .
C38 C 0.1961(3) 0.4499(3) 0.7078(3) 0.0516(8) Uani 1 1 d . . . . .
H38 H 0.251656 0.518155 0.733012 0.062 Uiso 1 1 calc R . . . .
C39 C 0.4216(4) -0.0705(4) 0.8211(3) 0.0628(10) Uani 1 1 d . . . . .
H39 H 0.505557 -0.048601 0.866778 0.075 Uiso 1 1 calc R . . . .
C40 C 0.3904(6) -0.1683(4) 0.7497(4) 0.0859(15) Uani 1 1 d . . . . .
H40 H 0.452514 -0.212372 0.747934 0.103 Uiso 1 1 calc R . . . .
C41 C 0.2675(6) -0.1997(4) 0.6817(4) 0.0876(16) Uani 1 1 d . . . . .
H41 H 0.245863 -0.265215 0.633262 0.105 Uiso 1 1 calc R . . . .
C42 C 0.1757(5) -0.1340(3) 0.6851(3) 0.0633(10) Uani 1 1 d . . . . .
H42 H 0.092556 -0.156183 0.638393 0.076 Uiso 1 1 calc R . . . .
O9 O 0.6884(4) 0.7266(3) 0.9086(2) 0.0863(10) Uani 1 1 d . . . . .
H9A H 0.620993 0.723235 0.924279 0.129 Uiso 1 1 d G . . . .
H9B H 0.659717 0.694517 0.848830 0.129 Uiso 1 1 d G . . . .
C43 C 0.5374(11) 0.4429(8) 0.4273(6) 0.048(2) Uani 0.5 1 d . . . A -1
H43A H 0.467174 0.426122 0.450173 0.057 Uiso 0.5 1 calc R . . A -1
H43B H 0.565908 0.374659 0.407167 0.057 Uiso 0.5 1 calc R . . A -1
C45 C 0.483(3) 0.485(2) 0.3396(15) 0.038(3) Uani 0.5 1 d . . . . .
C46 C 0.503(3) 0.517(2) 0.6809(16) 0.042(3) Uani 0.5 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 O1 2.068(2) 2_557 ?
Ni1 O1 2.068(2) . ?
Ni1 O8 2.099(2) 2_557 ?
Ni1 O8 2.099(2) . ?
Ni1 N4 2.069(2) 1_445 ?
Ni1 N4 2.069(2) 2_667 ?
Ni2 O3 2.055(2) . ?
Ni2 O4 2.073(2) . ?
Ni2 O6 2.128(2) . ?
Ni2 N1 2.069(2) . ?
Ni2 N5 2.079(3) . ?
Ni2 N8 2.081(2) 2_556 ?
O1 C1 1.247(4) . ?
O2 C1 1.251(4) . ?
O3 C6 1.251(3) . ?
O4 C45 1.27(2) 2_666 ?
O4 C46 1.20(3) . ?
O5 C45 1.24(3) . ?
O5 C46 1.25(3) 2_666 ?
O10 C45 1.54(2) 2_666 ?
O10 C46 1.26(2) . ?
O6 H6A 0.8700 . ?
O6 H6B 0.8685 . ?
O7 C6 1.257(4) . ?
O8 H8A 0.8634 . ?
O8 H8B 0.8634 . ?
N1 C15 1.305(4) . ?
N1 C26 1.374(4) . ?
N2 C15 1.357(3) . ?
N2 C16 1.420(3) . ?
N2 C25 1.387(4) . ?
N3 C18 1.427(4) . ?
N3 C19 1.351(4) . ?
N3 C21 1.386(4) . ?
N4 C19 1.314(4) . ?
N4 C20 1.375(4) . ?
N5 C27 1.302(4) . ?
N5 C38 1.372(4) . ?
N6 C27 1.354(4) . ?
N6 C28 1.430(4) . ?
N6 C37 1.376(4) . ?
N7 C30 1.436(4) . ?
N7 C31 1.346(3) . ?
N7 C33 1.387(4) . ?
N8 C31 1.318(4) . ?
N8 C32 1.375(3) . ?
C1 C2 1.537(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.510(5) . ?
C3 C4 1.391(5) . ?
C3 C42 1.389(5) . ?
C4 C5 1.510(5) . ?
C4 C39 1.398(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.526(4) . ?
C8 H8C 0.9700 . ?
C8 H8D 0.9700 . ?
C8 C9 1.503(12) . ?
C8 C46 1.53(2) . ?
C9 C14 1.498(10) . ?
C9 C10 1.401(8) . ?
C14 H14 0.9300 . ?
C14 C13 1.171(10) . ?
C13 H13 0.9300 . ?
C13 C12 1.555(14) . ?
C12 H12 0.9300 . ?
C12 C11 1.312(10) . ?
C11 H11 0.9300 . ?
C11 C10 1.440(10) . ?
C10 C43 1.501(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(4) . ?
C16 C24 1.392(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(4) . ?
C18 C22 1.386(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.343(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.382(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.387(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.349(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.386(4) . ?
C28 C36 1.383(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.387(4) . ?
C30 C34 1.374(4) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C32 C33 1.348(4) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C34 C35 1.382(5) . ?
C35 H35 0.9300 . ?
C35 C36 1.389(4) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C37 C38 1.346(5) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C39 C40 1.383(7) . ?
C40 H40 0.9300 . ?
C40 C41 1.368(8) . ?
C41 H41 0.9300 . ?
C41 C42 1.380(7) . ?
C42 H42 0.9300 . ?
O9 H9A 0.8500 . ?
O9 H9B 0.8501 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C43 C45 1.53(3) . ?
C45 C46 0.39(2) 2_666 ?

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 Ni1 O1 180.0 2_557 . ?
O1 Ni1 O8 88.09(9) . 2_557 ?
O1 Ni1 O8 91.91(9) . . ?
O1 Ni1 O8 91.91(9) 2_557 2_557 ?
O1 Ni1 O8 88.09(9) 2_557 . ?
O1 Ni1 N4 88.67(9) 2_557 2_667 ?
O1 Ni1 N4 91.33(9) . 2_667 ?
O1 Ni1 N4 88.67(9) . 1_445 ?
O1 Ni1 N4 91.33(9) 2_557 1_445 ?
O8 Ni1 O8 180.0 . 2_557 ?
N4 Ni1 O8 87.56(9) 2_667 . ?
N4 Ni1 O8 92.44(9) 2_667 2_557 ?
N4 Ni1 O8 87.56(9) 1_445 2_557 ?
N4 Ni1 O8 92.44(9) 1_445 . ?
N4 Ni1 N4 180.0 2_667 1_445 ?
O3 Ni2 O4 174.62(8) . . ?
O3 Ni2 O6 90.14(9) . . ?
O3 Ni2 N1 88.72(9) . . ?
O3 Ni2 N5 91.57(10) . . ?
O3 Ni2 N8 86.06(9) . 2_556 ?
O4 Ni2 O6 94.98(9) . . ?
O4 Ni2 N5 87.07(10) . . ?
O4 Ni2 N8 88.73(9) . 2_556 ?
N1 Ni2 O4 92.99(9) . . ?
N1 Ni2 O6 89.48(10) . . ?
N1 Ni2 N5 176.11(10) . . ?
N1 Ni2 N8 94.17(9) . 2_556 ?
N5 Ni2 O6 86.64(11) . . ?
N5 Ni2 N8 89.72(10) . 2_556 ?
N8 Ni2 O6 174.66(9) 2_556 . ?
C1 O1 Ni1 125.2(2) . . ?
C6 O3 Ni2 132.6(2) . . ?
C45 O4 Ni2 144.9(10) 2_666 . ?
C46 O4 Ni2 130.1(9) . . ?
C46 O4 C45 17.9(12) . 2_666 ?
C45 O5 C46 18.1(11) . 2_666 ?
C46 O10 C45 11.3(18) . 2_666 ?
Ni2 O6 H6A 110.8 . . ?
Ni2 O6 H6B 110.1 . . ?
H6A O6 H6B 103.3 . . ?
Ni1 O8 H8A 110.4 . . ?
Ni1 O8 H8B 110.1 . . ?
H8A O8 H8B 103.7 . . ?
C15 N1 Ni2 123.1(2) . . ?
C15 N1 C26 105.8(2) . . ?
C26 N1 Ni2 131.0(2) . . ?
C15 N2 C16 126.3(2) . . ?
C15 N2 C25 106.2(2) . . ?
C25 N2 C16 127.5(2) . . ?
C19 N3 C18 126.9(2) . . ?
C19 N3 C21 106.9(2) . . ?
C21 N3 C18 126.0(2) . . ?
C19 N4 Ni1 130.3(2) . 1_665 ?
C19 N4 C20 105.2(2) . . ?
C20 N4 Ni1 124.4(2) . 1_665 ?
C27 N5 Ni2 124.8(2) . . ?
C27 N5 C38 105.5(3) . . ?
C38 N5 Ni2 129.7(2) . . ?
C27 N6 C28 126.3(3) . . ?
C27 N6 C37 106.3(3) . . ?
C37 N6 C28 127.4(3) . . ?
C31 N7 C30 126.5(2) . . ?
C31 N7 C33 107.3(2) . . ?
C33 N7 C30 126.2(2) . . ?
C31 N8 Ni2 128.13(18) . 2_556 ?
C31 N8 C32 105.9(2) . . ?
C32 N8 Ni2 125.53(19) . 2_556 ?
O1 C1 O2 125.7(3) . . ?
O1 C1 C2 116.8(3) . . ?
O2 C1 C2 117.4(3) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 C1 112.8(3) . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C4 C3 C2 122.6(3) . . ?
C42 C3 C2 119.0(3) . . ?
C42 C3 C4 118.4(3) . . ?
C3 C4 C5 122.2(3) . . ?
C3 C4 C39 119.3(3) . . ?
C39 C4 C5 118.5(3) . . ?
C4 C5 H5A 108.3 . . ?
C4 C5 H5B 108.3 . . ?
C4 C5 C6 115.9(2) . . ?
H5A C5 H5B 107.4 . . ?
C6 C5 H5A 108.3 . . ?
C6 C5 H5B 108.3 . . ?
O3 C6 O7 125.4(3) . . ?
O3 C6 C5 117.5(3) . . ?
O7 C6 C5 117.0(3) . . ?
H8C C8 H8D 108.0 . . ?
C9 C8 H8C 109.4 . . ?
C9 C8 H8D 109.4 . . ?
C9 C8 C46 111.1(12) . . ?
C46 C8 H8C 109.4 . . ?
C46 C8 H8D 109.4 . . ?
C14 C9 C8 119.8(6) . . ?
C10 C9 C8 123.6(6) . . ?
C10 C9 C14 116.6(6) . . ?
C9 C14 H14 116.9 . . ?
C13 C14 C9 126.3(7) . . ?
C13 C14 H14 116.9 . . ?
C14 C13 H13 120.7 . . ?
C14 C13 C12 118.6(7) . . ?
C12 C13 H13 120.7 . . ?
C13 C12 H12 121.4 . . ?
C11 C12 C13 117.2(7) . . ?
C11 C12 H12 121.4 . . ?
C12 C11 H11 118.0 . . ?
C12 C11 C10 124.0(7) . . ?
C10 C11 H11 118.0 . . ?
C9 C10 C11 116.8(6) . . ?
C9 C10 C43 123.2(7) . . ?
C11 C10 C43 120.0(7) . . ?
N1 C15 N2 111.9(2) . . ?
N1 C15 H15 124.1 . . ?
N2 C15 H15 124.1 . . ?
C17 C16 N2 119.7(2) . . ?
C17 C16 C24 120.5(3) . . ?
C24 C16 N2 119.8(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 N3 120.0(2) . . ?
C17 C18 C22 121.0(3) . . ?
C22 C18 N3 119.0(3) . . ?
N3 C19 H19 124.2 . . ?
N4 C19 N3 111.5(2) . . ?
N4 C19 H19 124.2 . . ?
N4 C20 H20 124.6 . . ?
C21 C20 N4 110.9(3) . . ?
C21 C20 H20 124.6 . . ?
N3 C21 H21 127.3 . . ?
C20 C21 N3 105.5(3) . . ?
C20 C21 H21 127.3 . . ?
C18 C22 H22 120.7 . . ?
C23 C22 C18 118.7(3) . . ?
C23 C22 H22 120.7 . . ?
C22 C23 H23 119.1 . . ?
C22 C23 C24 121.7(3) . . ?
C24 C23 H23 119.1 . . ?
C16 C24 H24 120.7 . . ?
C23 C24 C16 118.6(3) . . ?
C23 C24 H24 120.7 . . ?
N2 C25 H25 127.0 . . ?
C26 C25 N2 106.0(3) . . ?
C26 C25 H25 127.0 . . ?
N1 C26 H26 124.9 . . ?
C25 C26 N1 110.2(3) . . ?
C25 C26 H26 124.9 . . ?
N5 C27 N6 111.9(3) . . ?
N5 C27 H27 124.1 . . ?
N6 C27 H27 124.1 . . ?
C29 C28 N6 119.6(3) . . ?
C36 C28 N6 120.3(3) . . ?
C36 C28 C29 120.1(3) . . ?
C28 C29 H29 120.4 . . ?
C28 C29 C30 119.2(3) . . ?
C30 C29 H29 120.4 . . ?
C29 C30 N7 118.3(3) . . ?
C34 C30 N7 120.2(3) . . ?
C34 C30 C29 121.5(3) . . ?
N7 C31 H31 124.5 . . ?
N8 C31 N7 111.0(2) . . ?
N8 C31 H31 124.5 . . ?
N8 C32 H32 124.9 . . ?
C33 C32 N8 110.2(3) . . ?
C33 C32 H32 124.9 . . ?
N7 C33 H33 127.2 . . ?
C32 C33 N7 105.6(2) . . ?
C32 C33 H33 127.2 . . ?
C30 C34 H34 120.6 . . ?
C30 C34 C35 118.7(3) . . ?
C35 C34 H34 120.6 . . ?
C34 C35 H35 119.6 . . ?
C34 C35 C36 120.9(3) . . ?
C36 C35 H35 119.6 . . ?
C28 C36 C35 119.6(3) . . ?
C28 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
N6 C37 H37 127.0 . . ?
C38 C37 N6 106.1(3) . . ?
C38 C37 H37 127.0 . . ?
N5 C38 H38 124.9 . . ?
C37 C38 N5 110.2(3) . . ?
C37 C38 H38 124.9 . . ?
C4 C39 H39 119.4 . . ?
C40 C39 C4 121.1(4) . . ?
C40 C39 H39 119.4 . . ?
C39 C40 H40 120.3 . . ?
C41 C40 C39 119.5(4) . . ?
C41 C40 H40 120.3 . . ?
C40 C41 H41 120.1 . . ?
C40 C41 C42 119.9(4) . . ?
C42 C41 H41 120.1 . . ?
C3 C42 H42 119.1 . . ?
C41 C42 C3 121.8(4) . . ?
C41 C42 H42 119.1 . . ?
H9A O9 H9B 104.5 . . ?
C10 C43 H43A 108.4 . . ?
C10 C43 H43B 108.4 . . ?
C10 C43 C45 115.6(12) . . ?
H43A C43 H43B 107.5 . . ?
C45 C43 H43A 108.4 . . ?
C45 C43 H43B 108.4 . . ?
O4 C45 O10 99.7(11) 2_666 2_666 ?
O4 C45 C43 115.7(19) 2_666 . ?
O5 C45 O4 126(2) . 2_666 ?
O5 C45 O10 42.6(8) . 2_666 ?
O5 C45 C43 118.6(16) . . ?
C43 C45 O10 130.8(18) . 2_666 ?
C46 C45 O4 70(7) 2_666 2_666 ?
C46 C45 O5 82(8) 2_666 . ?
C46 C45 O10 39(7) 2_666 2_666 ?
C46 C45 C43 124(9) 2_666 . ?
O4 C46 O5 133(3) . 2_666 ?
O4 C46 O10 122.7(18) . . ?
O4 C46 C8 120.9(17) . . ?
O5 C46 C8 84.8(14) 2_666 . ?
C45 C46 O4 92(7) 2_666 . ?
C45 C46 O5 80(8) 2_666 2_666 ?
C45 C46 O10 129(9) 2_666 . ?
C45 C46 C8 44(7) 2_666 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 O1 C1 O2 21.1(5) . . . . ?
Ni1 O1 C1 C2 -157.8(2) . . . . ?
Ni1 N4 C19 N3 -176.98(19) 1_665 . . . ?
Ni1 N4 C20 C21 177.2(2) 1_665 . . . ?
Ni2 O3 C6 O7 8.6(5) . . . . ?
Ni2 O3 C6 C5 -173.1(2) . . . . ?
Ni2 O4 C46 O5 72.4(19) . . . 2_666 ?
Ni2 O4 C46 O10 10(4) . . . . ?
Ni2 O4 C46 C8 -173.5(10) . . . . ?
Ni2 O4 C46 C45 151(8) . . . 2_666 ?
Ni2 N1 C15 N2 177.76(18) . . . . ?
Ni2 N1 C26 C25 -177.4(2) . . . . ?
Ni2 N5 C27 N6 -176.9(2) . . . . ?
Ni2 N5 C38 C37 177.6(3) . . . . ?
Ni2 N8 C31 N7 -173.04(18) 2_556 . . . ?
Ni2 N8 C32 C33 172.8(2) 2_556 . . . ?
O1 C1 C2 C3 89.6(4) . . . . ?
O2 C1 C2 C3 -89.4(4) . . . . ?
N2 C16 C17 C18 177.3(2) . . . . ?
N2 C16 C24 C23 -178.0(3) . . . . ?
N2 C25 C26 N1 0.2(4) . . . . ?
N3 C18 C22 C23 -179.7(3) . . . . ?
N4 C20 C21 N3 0.1(4) . . . . ?
N6 C28 C29 C30 179.6(3) . . . . ?
N6 C28 C36 C35 179.9(3) . . . . ?
N6 C37 C38 N5 -0.6(4) . . . . ?
N7 C30 C34 C35 178.5(3) . . . . ?
N8 C32 C33 N7 0.5(4) . . . . ?
C1 C2 C3 C4 -91.1(4) . . . . ?
C1 C2 C3 C42 89.8(4) . . . . ?
C2 C3 C4 C5 3.4(4) . . . . ?
C2 C3 C4 C39 -178.2(3) . . . . ?
C2 C3 C42 C41 178.9(4) . . . . ?
C3 C4 C5 C6 -81.0(4) . . . . ?
C3 C4 C39 C40 -1.2(6) . . . . ?
C4 C3 C42 C41 -0.2(6) . . . . ?
C4 C5 C6 O3 10.8(4) . . . . ?
C4 C5 C6 O7 -170.9(3) . . . . ?
C4 C39 C40 C41 1.0(7) . . . . ?
C5 C4 C39 C40 177.2(4) . . . . ?
C8 C9 C14 C13 177.1(9) . . . . ?
C8 C9 C10 C11 179.5(6) . . . . ?
C8 C9 C10 C43 1.8(8) . . . . ?
C9 C8 C46 O4 -92(2) . . . . ?
C9 C8 C46 O5 45.2(14) . . . 2_666 ?
C9 C8 C46 C45 -36(11) . . . 2_666 ?
C9 C14 C13 C12 6.7(12) . . . . ?
C9 C10 C43 C45 101.5(12) . . . . ?
C14 C9 C10 C11 -0.8(8) . . . . ?
C14 C9 C10 C43 -178.5(6) . . . . ?
C14 C13 C12 C11 -7.8(11) . . . . ?
C13 C12 C11 C10 4.8(10) . . . . ?
C12 C11 C10 C9 -0.9(9) . . . . ?
C12 C11 C10 C43 176.9(7) . . . . ?
C11 C10 C43 C45 -76.1(13) . . . . ?
C10 C9 C14 C13 -2.6(11) . . . . ?
C10 C43 C45 O4 3(2) . . . 2_666 ?
C10 C43 C45 O5 -175.5(14) . . . . ?
C10 C43 C45 C46 85(10) . . . 2_666 ?
C15 N1 C26 C25 -0.4(4) . . . . ?
C15 N2 C16 C17 2.4(4) . . . . ?
C15 N2 C16 C24 -178.4(3) . . . . ?
C15 N2 C25 C26 0.1(4) . . . . ?
C16 N2 C15 N1 -178.1(2) . . . . ?
C16 N2 C25 C26 177.9(3) . . . . ?
C16 C17 C18 N3 -178.9(2) . . . . ?
C16 C17 C18 C22 1.2(4) . . . . ?
C17 C16 C24 C23 1.3(5) . . . . ?
C17 C18 C22 C23 0.3(5) . . . . ?
C18 N3 C19 N4 175.1(3) . . . . ?
C18 N3 C21 C20 -175.3(3) . . . . ?
C18 C22 C23 C24 -1.0(5) . . . . ?
C19 N3 C18 C17 26.1(4) . . . . ?
C19 N3 C18 C22 -153.9(3) . . . . ?
C19 N3 C21 C20 0.0(4) . . . . ?
C19 N4 C20 C21 -0.1(4) . . . . ?
C20 N4 C19 N3 0.1(3) . . . . ?
C21 N3 C18 C17 -159.5(3) . . . . ?
C21 N3 C18 C22 20.4(4) . . . . ?
C21 N3 C19 N4 -0.1(3) . . . . ?
C22 C23 C24 C16 0.2(5) . . . . ?
C24 C16 C17 C18 -1.9(4) . . . . ?
C25 N2 C15 N1 -0.3(3) . . . . ?
C25 N2 C16 C17 -175.0(3) . . . . ?
C25 N2 C16 C24 4.3(4) . . . . ?
C26 N1 C15 N2 0.4(3) . . . . ?
C27 N5 C38 C37 -0.4(4) . . . . ?
C27 N6 C28 C29 -10.9(4) . . . . ?
C27 N6 C28 C36 169.4(3) . . . . ?
C27 N6 C37 C38 1.3(4) . . . . ?
C28 N6 C27 N5 -178.8(3) . . . . ?
C28 N6 C37 C38 178.4(3) . . . . ?
C28 C29 C30 N7 -178.0(3) . . . . ?
C28 C29 C30 C34 0.7(4) . . . . ?
C29 C28 C36 C35 0.2(5) . . . . ?
C29 C30 C34 C35 -0.3(5) . . . . ?
C30 N7 C31 N8 -178.6(3) . . . . ?
C30 N7 C33 C32 178.6(3) . . . . ?
C30 C34 C35 C36 -0.2(5) . . . . ?
C31 N7 C30 C29 -111.7(3) . . . . ?
C31 N7 C30 C34 69.5(4) . . . . ?
C31 N7 C33 C32 -0.8(3) . . . . ?
C31 N8 C32 C33 0.1(3) . . . . ?
C32 N8 C31 N7 -0.6(3) . . . . ?
C33 N7 C30 C29 69.0(4) . . . . ?
C33 N7 C30 C34 -109.8(3) . . . . ?
C33 N7 C31 N8 0.9(3) . . . . ?
C34 C35 C36 C28 0.3(5) . . . . ?
C36 C28 C29 C30 -0.7(4) . . . . ?
C37 N6 C27 N5 -1.6(4) . . . . ?
C37 N6 C28 C29 172.5(3) . . . . ?
C37 N6 C28 C36 -7.2(5) . . . . ?
C38 N5 C27 N6 1.3(4) . . . . ?
C39 C4 C5 C6 100.6(4) . . . . ?
C39 C40 C41 C42 -0.3(8) . . . . ?
C40 C41 C42 C3 -0.1(7) . . . . ?
C42 C3 C4 C5 -177.6(3) . . . . ?
C42 C3 C4 C39 0.8(5) . . . . ?
C45 O4 C46 O5 -79(9) 2_666 . . 2_666 ?
C45 O4 C46 O10 -141(11) 2_666 . . . ?
C45 O4 C46 C8 35(7) 2_666 . . . ?
C45 O10 C46 O4 126(14) 2_666 . . . ?
C46 O5 C45 O4 58(7) 2_666 . . 2_666 ?
C46 O5 C45 C43 -124(9) 2_666 . . . ?
C46 C8 C9 C14 -75.0(13) . . . . ?
C46 C8 C9 C10 104.7(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# Crystallographic Data Centre (CCDC).
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# 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_111
_database_code_depnum_ccdc_archive 'CCDC 1966121'
loop_
_audit_author_name
_audit_author_address
CCDAS
;YANANUnversity
China
;
_audit_update_record             
;
2019-11-16 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;
_audit_creation_date             2019-02-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 Co N4 O5'
_chemical_formula_sum            'C22 H20 Co N4 O5'
_chemical_formula_weight         479.35
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.4014(7)
_cell_length_b                   13.6927(7)
_cell_length_c                   12.6869(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.129(2)
_cell_angle_gamma                90
_cell_volume                     2079.68(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.508
_cell_measurement_theta_min      2.975
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0629 before and 0.0529 after correction.
The Ratio of minimum to maximum transmission is 0.8991.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31848
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.552
_diffrn_reflns_theta_min         2.975
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_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                4064
_reflns_number_total             4780
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4780
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0978P)²+4.1635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1761
_refine_ls_wR_factor_ref         0.1835
_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 O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
3.a Rotating group:
 O5(H5A,H5B)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C13(H13), C19(H19), C21(H21), C11(H11), C22(H22),
 C20(H20), C15(H15), C7(H7), C18(H18), C6(H6), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.54142(4) 0.10022(3) 0.34910(4) 0.02610(17) Uani 1 1 d . . . . .
O2 O 0.6490(2) 0.11743(19) 0.5165(2) 0.0387(6) Uani 1 1 d . . . . .
O1 O 0.7107(2) 0.16074(18) 0.3766(2) 0.0335(5) Uani 1 1 d . . . . .
O4 O 0.9869(2) 0.3950(2) 0.6828(2) 0.0413(6) Uani 1 1 d . . . . .
O5 O 0.3837(2) 0.05075(19) 0.3697(2) 0.0424(6) Uani 1 1 d . . . . .
H5A H 0.390535 -0.005722 0.403433 0.064 Uiso 1 1 d GR . . . .
H5B H 0.337227 0.037651 0.306282 0.064 Uiso 1 1 d GR . . . .
N4 N 0.6018(3) 0.9565(2) 0.3478(2) 0.0330(6) Uani 1 1 d . . . . .
O3 O 0.8178(3) 0.4594(3) 0.6559(3) 0.0642(10) Uani 1 1 d . . . . .
N3 N 0.6087(3) 0.7958(2) 0.3415(3) 0.0339(6) Uani 1 1 d . . . . .
N2 N 0.4709(3) 0.40512(19) 0.3470(3) 0.0335(6) Uani 1 1 d . . . . .
C1 C 0.7263(3) 0.1496(2) 0.4775(3) 0.0319(7) Uani 1 1 d . . . . .
N1 N 0.4803(2) 0.2442(2) 0.3533(3) 0.0344(6) Uani 1 1 d . . . . .
C3 C 0.9271(3) 0.2100(3) 0.5054(3) 0.0398(8) Uani 1 1 d . . . . .
C8 C 0.9374(3) 0.3073(3) 0.4792(3) 0.0387(8) Uani 1 1 d . . . . .
C10 C 0.8909(3) 0.4154(3) 0.6249(3) 0.0384(8) Uani 1 1 d . . . . .
C12 C 0.3768(3) 0.2732(3) 0.3612(4) 0.0434(9) Uani 1 1 d . . . . .
H12 H 0.320023 0.231207 0.367966 0.052 Uiso 1 1 calc R . . . .
C16 C 0.6384(5) 0.6229(3) 0.3165(5) 0.0669(15) Uani 1 1 d . U . . .
H16 H 0.704748 0.637373 0.298757 0.080 Uiso 1 1 calc R . . . .
C13 C 0.3693(3) 0.3719(3) 0.3576(4) 0.0430(9) Uani 1 1 d . . . . .
H13 H 0.308036 0.409548 0.361523 0.052 Uiso 1 1 calc R . . . .
C14 C 0.5053(3) 0.5046(2) 0.3444(3) 0.0343(7) Uani 1 1 d . . . . .
C19 C 0.4428(3) 0.5775(3) 0.3727(4) 0.0402(9) Uani 1 1 d . . . . .
H19 H 0.377512 0.562653 0.392405 0.048 Uiso 1 1 calc R . . . .
C17 C 0.5739(3) 0.6968(2) 0.3427(3) 0.0338(7) Uani 1 1 d . . . . .
C21 C 0.7044(4) 0.8296(3) 0.3244(6) 0.0761(17) Uani 1 1 d . U . . .
H21 H 0.762740 0.792649 0.311862 0.091 Uiso 1 1 calc R . . . .
C11 C 0.5345(3) 0.3251(2) 0.3448(3) 0.0350(8) Uani 1 1 d . . . . .
H11 H 0.607334 0.327135 0.338002 0.042 Uiso 1 1 calc R . . . .
C22 C 0.6991(4) 0.9281(3) 0.3290(6) 0.0722(16) Uani 1 1 d . U . . .
H22 H 0.754815 0.970429 0.320333 0.087 Uiso 1 1 calc R . . . .
C20 C 0.5499(3) 0.8747(3) 0.3553(4) 0.0430(9) Uani 1 1 d . U . . .
H20 H 0.479730 0.871553 0.368795 0.052 Uiso 1 1 calc R . . . .
C2 C 0.8379(4) 0.1744(4) 0.5562(4) 0.0552(12) Uani 1 1 d . . . . .
H2A H 0.825418 0.224183 0.606172 0.066 Uiso 1 1 calc R . . . .
H2B H 0.865483 0.116688 0.599121 0.066 Uiso 1 1 calc R . . . .
C15 C 0.6029(5) 0.5271(3) 0.3172(5) 0.0696(16) Uani 1 1 d . U . . .
H15 H 0.645606 0.477206 0.298945 0.084 Uiso 1 1 calc R . . . .
C7 C 1.0210(4) 0.3343(4) 0.4308(4) 0.0611(13) Uani 1 1 d . . . . .
H7 H 1.026529 0.399754 0.413170 0.073 Uiso 1 1 calc R . . . .
C18 C 0.4777(3) 0.6741(2) 0.3718(4) 0.0415(9) Uani 1 1 d . . . . .
H18 H 0.435416 0.723780 0.391043 0.050 Uiso 1 1 calc R . . . .
C9 C 0.8620(4) 0.3830(3) 0.5053(4) 0.0507(10) Uani 1 1 d . . . . .
H9A H 0.786290 0.357805 0.485761 0.061 Uiso 1 1 calc R . . . .
H9B H 0.863533 0.439851 0.460139 0.061 Uiso 1 1 calc R . . . .
C6 C 1.0938(5) 0.2717(7) 0.4083(6) 0.090(2) Uani 1 1 d . . . . .
H6 H 1.148560 0.293029 0.375662 0.108 Uiso 1 1 calc R . . . .
C5 C 1.0867(6) 0.1753(7) 0.4338(7) 0.101(3) Uani 1 1 d . . . . .
H5 H 1.137428 0.130528 0.419478 0.121 Uiso 1 1 calc R . . . .
C4 C 1.0041(5) 0.1449(4) 0.4808(6) 0.0792(18) Uani 1 1 d . . . . .
H4 H 0.999319 0.078956 0.496713 0.095 Uiso 1 1 calc R . . . .


_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 O2 2.206(3) . ?
Co1 O1 2.199(2) . ?
Co1 O4 2.042(3) 4_565 ?
Co1 O5 2.149(3) . ?
Co1 N4 2.107(3) 1_545 ?
Co1 N1 2.118(3) . ?
O2 C1 1.267(4) . ?
O1 C1 1.253(4) . ?
O4 C10 1.256(5) . ?
O5 H5A 0.8774 . ?
O5 H5B 0.8770 . ?
N4 C22 1.347(6) . ?
N4 C20 1.308(5) . ?
O3 C10 1.235(5) . ?
N3 C17 1.425(4) . ?
N3 C21 1.343(6) . ?
N3 C20 1.341(5) . ?
N2 C13 1.379(5) . ?
N2 C14 1.430(4) . ?
N2 C11 1.354(4) . ?
C1 C2 1.519(5) . ?
N1 C12 1.372(5) . ?
N1 C11 1.315(4) . ?
C3 C8 1.386(6) . ?
C3 C2 1.500(6) . ?
C3 C4 1.400(7) . ?
C8 C7 1.387(6) . ?
C8 C9 1.490(6) . ?
C10 C9 1.531(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.354(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(5) . ?
C16 C15 1.384(6) . ?
C13 H13 0.9300 . ?
C14 C19 1.368(5) . ?
C14 C15 1.378(6) . ?
C19 H19 0.9300 . ?
C19 C18 1.393(5) . ?
C17 C18 1.373(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.353(6) . ?
C11 H11 0.9300 . ?
C22 H22 0.9300 . ?
C20 H20 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C15 H15 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.329(9) . ?
C18 H18 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C5 1.367(12) . ?
C5 H5 0.9300 . ?
C5 C4 1.378(10) . ?
C4 H4 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 Co1 O2 59.63(9) . . ?
O4 Co1 O2 160.99(11) 4_565 . ?
O4 Co1 O1 101.37(10) 4_565 . ?
O4 Co1 O5 93.95(12) 4_565 . ?
O4 Co1 N4 92.53(12) 4_565 1_545 ?
O4 Co1 N1 88.41(12) 4_565 . ?
O5 Co1 O2 104.93(11) . . ?
O5 Co1 O1 163.98(11) . . ?
N4 Co1 O2 88.88(11) 1_545 . ?
N4 Co1 O1 91.54(10) 1_545 . ?
N4 Co1 O5 92.45(11) 1_545 . ?
N4 Co1 N1 178.93(12) 1_545 . ?
N1 Co1 O2 90.39(11) . . ?
N1 Co1 O1 88.76(10) . . ?
N1 Co1 O5 86.98(11) . . ?
C1 O2 Co1 89.4(2) . . ?
C1 O1 Co1 90.1(2) . . ?
C10 O4 Co1 127.2(3) . 4_666 ?
Co1 O5 H5A 111.2 . . ?
Co1 O5 H5B 110.8 . . ?
H5A O5 H5B 102.9 . . ?
C22 N4 Co1 127.4(3) . 1_565 ?
C20 N4 Co1 128.1(3) . 1_565 ?
C20 N4 C22 104.3(3) . . ?
C21 N3 C17 127.8(3) . . ?
C20 N3 C17 126.0(3) . . ?
C20 N3 C21 106.1(3) . . ?
C13 N2 C14 127.0(3) . . ?
C11 N2 C13 106.7(3) . . ?
C11 N2 C14 126.2(3) . . ?
O2 C1 C2 118.2(3) . . ?
O1 C1 O2 120.7(3) . . ?
O1 C1 C2 121.0(3) . . ?
C12 N1 Co1 128.2(2) . . ?
C11 N1 Co1 126.0(2) . . ?
C11 N1 C12 105.7(3) . . ?
C8 C3 C2 122.6(4) . . ?
C8 C3 C4 116.6(5) . . ?
C4 C3 C2 120.8(5) . . ?
C3 C8 C7 119.3(4) . . ?
C3 C8 C9 120.9(4) . . ?
C7 C8 C9 119.8(4) . . ?
O4 C10 C9 117.1(4) . . ?
O3 C10 O4 125.8(4) . . ?
O3 C10 C9 117.1(4) . . ?
N1 C12 H12 125.0 . . ?
C13 C12 N1 110.1(3) . . ?
C13 C12 H12 125.0 . . ?
C17 C16 H16 120.4 . . ?
C17 C16 C15 119.2(4) . . ?
C15 C16 H16 120.4 . . ?
N2 C13 H13 127.0 . . ?
C12 C13 N2 106.0(3) . . ?
C12 C13 H13 127.0 . . ?
C19 C14 N2 119.7(3) . . ?
C19 C14 C15 119.8(3) . . ?
C15 C14 N2 120.4(3) . . ?
C14 C19 H19 120.3 . . ?
C14 C19 C18 119.5(4) . . ?
C18 C19 H19 120.3 . . ?
C16 C17 N3 119.9(3) . . ?
C18 C17 N3 120.3(3) . . ?
C18 C17 C16 119.8(3) . . ?
N3 C21 H21 126.8 . . ?
N3 C21 C22 106.4(4) . . ?
C22 C21 H21 126.8 . . ?
N2 C11 H11 124.2 . . ?
N1 C11 N2 111.5(3) . . ?
N1 C11 H11 124.2 . . ?
N4 C22 C21 110.6(4) . . ?
N4 C22 H22 124.7 . . ?
C21 C22 H22 124.7 . . ?
N4 C20 N3 112.7(3) . . ?
N4 C20 H20 123.7 . . ?
N3 C20 H20 123.7 . . ?
C1 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
C3 C2 C1 116.0(3) . . ?
C3 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C16 C15 H15 119.5 . . ?
C14 C15 C16 121.0(4) . . ?
C14 C15 H15 119.5 . . ?
C8 C7 H7 118.3 . . ?
C6 C7 C8 123.4(6) . . ?
C6 C7 H7 118.3 . . ?
C19 C18 H18 119.6 . . ?
C17 C18 C19 120.7(3) . . ?
C17 C18 H18 119.6 . . ?
C8 C9 C10 115.1(3) . . ?
C8 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C7 C6 H6 120.6 . . ?
C7 C6 C5 118.9(6) . . ?
C5 C6 H6 120.6 . . ?
C6 C5 H5 120.1 . . ?
C6 C5 C4 119.7(6) . . ?
C4 C5 H5 120.1 . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 122.1(6) . . ?
C5 C4 H4 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_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 O2 C1 O1 2.8(3) . . . . ?
Co1 O2 C1 C2 -177.4(3) . . . . ?
Co1 O1 C1 O2 -2.8(3) . . . . ?
Co1 O1 C1 C2 177.4(4) . . . . ?
Co1 O4 C10 O3 14.5(6) 4_666 . . . ?
Co1 O4 C10 C9 -165.6(3) 4_666 . . . ?
Co1 N4 C22 C21 -174.1(4) 1_565 . . . ?
Co1 N4 C20 N3 174.1(3) 1_565 . . . ?
Co1 N1 C12 C13 -177.9(3) . . . . ?
Co1 N1 C11 N2 178.0(3) . . . . ?
O2 C1 C2 C3 178.7(4) . . . . ?
O1 C1 C2 C3 -1.6(6) . . . . ?
O4 C10 C9 C8 16.8(6) . . . . ?
O3 C10 C9 C8 -163.3(4) . . . . ?
N3 C17 C18 C19 179.7(4) . . . . ?
N3 C21 C22 N4 -0.4(8) . . . . ?
N2 C14 C19 C18 178.9(4) . . . . ?
N2 C14 C15 C16 -178.6(5) . . . . ?
N1 C12 C13 N2 0.1(5) . . . . ?
C3 C8 C7 C6 -0.5(8) . . . . ?
C3 C8 C9 C10 77.8(5) . . . . ?
C8 C3 C2 C1 85.9(5) . . . . ?
C8 C3 C4 C5 0.5(8) . . . . ?
C8 C7 C6 C5 0.0(10) . . . . ?
C12 N1 C11 N2 0.2(5) . . . . ?
C16 C17 C18 C19 -1.6(7) . . . . ?
C13 N2 C14 C19 12.0(6) . . . . ?
C13 N2 C14 C15 -170.3(5) . . . . ?
C13 N2 C11 N1 -0.1(5) . . . . ?
C14 N2 C13 C12 -177.2(4) . . . . ?
C14 N2 C11 N1 177.1(3) . . . . ?
C14 C19 C18 C17 0.1(7) . . . . ?
C19 C14 C15 C16 -0.9(9) . . . . ?
C17 N3 C21 C22 178.9(5) . . . . ?
C17 N3 C20 N4 -178.6(3) . . . . ?
C17 C16 C15 C14 -0.6(10) . . . . ?
C21 N3 C17 C16 -4.9(7) . . . . ?
C21 N3 C17 C18 173.8(5) . . . . ?
C21 N3 C20 N4 0.2(6) . . . . ?
C11 N2 C13 C12 0.0(5) . . . . ?
C11 N2 C14 C19 -164.7(4) . . . . ?
C11 N2 C14 C15 13.1(7) . . . . ?
C11 N1 C12 C13 -0.2(5) . . . . ?
C22 N4 C20 N3 -0.4(5) . . . . ?
C20 N4 C22 C21 0.5(7) . . . . ?
C20 N3 C17 C16 173.6(5) . . . . ?
C20 N3 C17 C18 -7.7(6) . . . . ?
C20 N3 C21 C22 0.1(7) . . . . ?
C2 C3 C8 C7 -179.0(4) . . . . ?
C2 C3 C8 C9 2.8(6) . . . . ?
C2 C3 C4 C5 179.8(6) . . . . ?
C15 C16 C17 N3 -179.4(5) . . . . ?
C15 C16 C17 C18 1.8(9) . . . . ?
C15 C14 C19 C18 1.2(7) . . . . ?
C7 C8 C9 C10 -100.4(5) . . . . ?
C7 C6 C5 C4 0.8(11) . . . . ?
C9 C8 C7 C6 177.7(5) . . . . ?
C6 C5 C4 C3 -1.1(11) . . . . ?
C4 C3 C8 C7 0.2(6) . . . . ?
C4 C3 C8 C9 -178.0(4) . . . . ?
C4 C3 C2 C1 -93.3(6) . . . . ?

_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_111_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1966120'
loop_
_audit_author_name
_audit_author_address
CCDAS
;YANANUnversity
China
;
_audit_update_record             
;
2019-11-16 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;
_audit_creation_date             2018-12-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H23 Co N6 O4'
_chemical_formula_sum            'C28 H23 Co N6 O4'
_chemical_formula_weight         566.45
_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                   9.031(5)
_cell_length_b                   9.063(6)
_cell_length_c                   16.232(10)
_cell_angle_alpha                96.661(9)
_cell_angle_beta                 92.025(9)
_cell_angle_gamma                111.918(8)
_cell_volume                     1219.8(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4625
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.330
_cell_measurement_theta_min      2.446
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.817
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0339 before and 0.0189 after correction.
The Ratio of minimum to maximum transmission is 0.8923.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0088
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7553
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.368
_diffrn_reflns_theta_min         1.268
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'CCD area detector'
_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                4889
_reflns_number_total             5585
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5585
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0635P)²+0.7717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1168
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C25(H25), C28(H28), C23(H23), C27(H27), C12(H12), C8(H8), C24(H24),
 C15(H15), C22(H22), C16(H16), C18(H18), C6(H6), C13(H13), C21(H21), C19(H19),
 C4(H4), C20(H20), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.14069(3) 0.21663(3) 0.76578(2) 0.03331(10) Uani 1 1 d . . . . .
O4 O 0.3816(2) 0.3583(2) 0.81920(14) 0.0657(6) Uani 1 1 d . . . . .
O2 O 1.1421(2) 1.0092(2) 0.79494(14) 0.0576(5) Uani 1 1 d . . . . .
O3 O 0.2240(2) 0.4854(3) 0.80715(14) 0.0686(6) Uani 1 1 d . . . . .
N1 N 0.1613(2) 0.2707(2) 0.64559(11) 0.0396(4) Uani 1 1 d . . . . .
N5 N -0.0748(2) 0.1954(2) 0.80948(12) 0.0402(4) Uani 1 1 d . . . . .
N6 N -0.2816(2) 0.1387(2) 0.88512(11) 0.0333(4) Uani 1 1 d . . . . .
N3 N 0.4281(2) 0.9393(2) 0.36564(12) 0.0422(4) Uani 1 1 d . . . . .
N2 N 0.2126(2) 0.4079(2) 0.53931(11) 0.0418(4) Uani 1 1 d . . . . .
O1 O 0.9846(3) 0.9053(3) 0.68095(14) 0.0839(7) Uani 1 1 d . . . . .
C11 C 0.2151(3) 0.4160(3) 0.62298(14) 0.0438(5) Uani 1 1 d . . . . .
H11 H 0.249915 0.511168 0.659853 0.053 Uiso 1 1 calc R . . . .
C26 C -0.3928(2) 0.0674(2) 0.94349(12) 0.0315(4) Uani 1 1 d . . . . .
C25 C -0.1545(3) 0.1024(3) 0.86311(13) 0.0367(4) Uani 1 1 d . . . . .
H25 H -0.127187 0.022961 0.883004 0.044 Uiso 1 1 calc R . . . .
C3 C 0.9086(3) 0.6896(2) 0.83852(15) 0.0397(5) Uani 1 1 d . . . . .
C7 C 0.6491(3) 0.6484(2) 0.88910(14) 0.0362(4) Uani 1 1 d . . . . .
C28 C -0.3422(2) 0.0117(2) 1.01127(13) 0.0343(4) Uani 1 1 d . . . . .
H28 H -0.236677 0.019985 1.018433 0.041 Uiso 1 1 calc R . . . .
N4 N 0.4483(3) 1.1653(3) 0.31834(19) 0.0717(8) Uani 1 1 d . . . . .
C23 C -0.1557(3) 0.2937(3) 0.79622(15) 0.0455(5) Uani 1 1 d . . . . .
H23 H -0.126684 0.371608 0.760792 0.055 Uiso 1 1 calc R . . . .
C27 C -0.5502(2) 0.0560(2) 0.93205(13) 0.0346(4) Uani 1 1 d . . . . .
H27 H -0.582933 0.093584 0.886646 0.041 Uiso 1 1 calc R . . . .
C10 C 0.3566(3) 0.4841(3) 0.83028(13) 0.0400(5) Uani 1 1 d . . . . .
C14 C 0.2633(3) 0.5412(3) 0.49326(13) 0.0408(5) Uani 1 1 d . . . . .
C17 C 0.3705(3) 0.8029(3) 0.40795(14) 0.0404(5) Uani 1 1 d . . . . .
C12 C 0.1236(3) 0.1659(3) 0.57258(14) 0.0455(5) Uani 1 1 d . . . . .
H12 H 0.083068 0.054567 0.568983 0.055 Uiso 1 1 calc R . . . .
C8 C 0.7513(3) 0.6777(2) 0.82576(14) 0.0377(4) Uani 1 1 d . . . . .
H8 H 0.713833 0.689665 0.773838 0.045 Uiso 1 1 calc R . . . .
C24 C -0.2831(3) 0.2610(3) 0.84183(15) 0.0428(5) Uani 1 1 d . . . . .
H24 H -0.356730 0.310427 0.843798 0.051 Uiso 1 1 calc R . . . .
C15 C 0.3491(3) 0.5357(3) 0.42485(15) 0.0477(6) Uani 1 1 d . . . . .
H15 H 0.371553 0.445111 0.408118 0.057 Uiso 1 1 calc R . . . .
C22 C 0.3648(4) 1.0524(4) 0.3609(2) 0.0656(8) Uani 1 1 d . . . . .
H22 H 0.272395 1.050176 0.385246 0.079 Uiso 1 1 calc R . . . .
C2 C 1.0185(4) 0.7249(3) 0.76863(19) 0.0548(7) Uani 1 1 d . . . . .
H2A H 1.119071 0.717300 0.785829 0.066 Uiso 1 1 calc R . . . .
H2B H 0.969591 0.645077 0.720203 0.066 Uiso 1 1 calc R . . . .
C1 C 1.0508(3) 0.8905(3) 0.74554(17) 0.0454(5) Uani 1 1 d . . . . .
C16 C 0.4015(3) 0.6665(3) 0.38137(16) 0.0483(6) Uani 1 1 d . . . . .
H16 H 0.457212 0.663031 0.334554 0.058 Uiso 1 1 calc R . . . .
C18 C 0.2838(3) 0.8066(3) 0.47635(16) 0.0492(6) Uani 1 1 d . . . . .
H18 H 0.263061 0.897830 0.494041 0.059 Uiso 1 1 calc R . . . .
C6 C 0.7073(3) 0.6308(3) 0.96656(14) 0.0456(5) Uani 1 1 d . . . . .
H6 H 0.641169 0.613789 1.010037 0.055 Uiso 1 1 calc R . . . .
C13 C 0.1540(3) 0.2486(3) 0.50667(15) 0.0484(6) Uani 1 1 d . . . . .
H13 H 0.138296 0.205895 0.450652 0.058 Uiso 1 1 calc R . . . .
C21 C 0.5691(3) 1.1202(3) 0.29208(18) 0.0558(7) Uani 1 1 d . . . . .
H21 H 0.647970 1.176685 0.259585 0.067 Uiso 1 1 calc R . . . .
C19 C 0.2281(3) 0.6745(3) 0.51833(16) 0.0501(6) Uani 1 1 d . . . . .
H19 H 0.167232 0.675523 0.563258 0.060 Uiso 1 1 calc R . . . .
C9 C 0.4802(3) 0.6404(3) 0.87459(17) 0.0454(5) Uani 1 1 d . . . . .
H9A H 0.483273 0.725363 0.842613 0.054 Uiso 1 1 calc R . . . .
H9B H 0.443516 0.663470 0.928208 0.054 Uiso 1 1 calc R . . . .
C4 C 0.9633(3) 0.6680(3) 0.91544(17) 0.0487(6) Uani 1 1 d . . . . .
H4 H 1.067662 0.673338 0.924178 0.058 Uiso 1 1 calc R . . . .
C20 C 0.5580(3) 0.9824(3) 0.31984(17) 0.0515(6) Uani 1 1 d . . . . .
H20 H 0.625554 0.927201 0.309793 0.062 Uiso 1 1 calc R . . . .
C5 C 0.8623(3) 0.6383(3) 0.97940(16) 0.0536(6) Uani 1 1 d . . . . .
H5 H 0.898932 0.623565 1.030874 0.064 Uiso 1 1 calc R . . . .


_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 O4 2.158(2) . ?
Co1 O2 1.996(2) 1_445 ?
Co1 O3 2.273(3) . ?
Co1 N1 2.064(2) . ?
Co1 N5 2.043(2) . ?
O4 C10 1.237(3) . ?
O2 C1 1.253(3) . ?
O3 C10 1.247(3) . ?
N1 C11 1.324(3) . ?
N1 C12 1.375(3) . ?
N5 C25 1.322(3) . ?
N5 C23 1.377(3) . ?
N6 C26 1.431(3) . ?
N6 C25 1.355(3) . ?
N6 C24 1.383(3) . ?
N3 C17 1.419(3) . ?
N3 C22 1.355(3) . ?
N3 C20 1.367(3) . ?
N2 C11 1.351(3) . ?
N2 C14 1.431(3) . ?
N2 C13 1.371(3) . ?
O1 C1 1.234(3) . ?
C11 H11 0.9300 . ?
C26 C28 1.392(3) . ?
C26 C27 1.390(3) . ?
C25 H25 0.9300 . ?
C3 C8 1.390(3) . ?
C3 C2 1.517(3) . ?
C3 C4 1.388(4) . ?
C7 C8 1.388(3) . ?
C7 C6 1.395(3) . ?
C7 C9 1.508(3) . ?
C28 H28 0.9300 . ?
C28 C27 1.384(3) 2_457 ?
N4 C22 1.311(4) . ?
N4 C21 1.366(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.347(3) . ?
C27 H27 0.9300 . ?
C10 C9 1.515(3) . ?
C14 C15 1.383(3) . ?
C14 C19 1.382(4) . ?
C17 C16 1.391(3) . ?
C17 C18 1.385(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.354(3) . ?
C8 H8 0.9300 . ?
C24 H24 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.388(3) . ?
C22 H22 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.514(3) . ?
C16 H16 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.384(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.383(4) . ?
C13 H13 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.347(4) . ?
C19 H19 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.390(4) . ?
C20 H20 0.9300 . ?
C5 H5 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 Co1 O3 58.14(7) . . ?
O2 Co1 O4 94.97(8) 1_445 . ?
O2 Co1 O3 145.43(9) 1_445 . ?
O2 Co1 N1 121.76(9) 1_445 . ?
O2 Co1 N5 96.95(8) 1_445 . ?
N1 Co1 O4 99.81(9) . . ?
N1 Co1 O3 86.62(8) . . ?
N5 Co1 O4 130.40(9) . . ?
N5 Co1 O3 87.44(7) . . ?
N5 Co1 N1 113.69(8) . . ?
C10 O4 Co1 93.48(15) . . ?
C1 O2 Co1 112.50(17) . 1_665 ?
C10 O3 Co1 87.90(17) . . ?
C11 N1 Co1 126.51(15) . . ?
C11 N1 C12 105.45(19) . . ?
C12 N1 Co1 128.04(16) . . ?
C25 N5 Co1 128.58(16) . . ?
C25 N5 C23 105.80(19) . . ?
C23 N5 Co1 125.13(15) . . ?
C25 N6 C26 126.96(18) . . ?
C25 N6 C24 107.30(17) . . ?
C24 N6 C26 125.73(18) . . ?
C22 N3 C17 127.4(2) . . ?
C22 N3 C20 105.6(2) . . ?
C20 N3 C17 127.0(2) . . ?
C11 N2 C14 126.3(2) . . ?
C11 N2 C13 107.39(19) . . ?
C13 N2 C14 126.31(19) . . ?
N1 C11 N2 111.0(2) . . ?
N1 C11 H11 124.5 . . ?
N2 C11 H11 124.5 . . ?
C28 C26 N6 119.91(19) . . ?
C27 C26 N6 119.33(19) . . ?
C27 C26 C28 120.76(18) . . ?
N5 C25 N6 110.73(19) . . ?
N5 C25 H25 124.6 . . ?
N6 C25 H25 124.6 . . ?
C8 C3 C2 120.0(2) . . ?
C4 C3 C8 119.4(2) . . ?
C4 C3 C2 120.6(2) . . ?
C8 C7 C6 118.6(2) . . ?
C8 C7 C9 120.3(2) . . ?
C6 C7 C9 121.0(2) . . ?
C26 C28 H28 120.1 . . ?
C27 C28 C26 119.72(19) 2_457 . ?
C27 C28 H28 120.1 2_457 . ?
C22 N4 C21 104.6(2) . . ?
N5 C23 H23 124.8 . . ?
C24 C23 N5 110.4(2) . . ?
C24 C23 H23 124.8 . . ?
C26 C27 H27 120.2 . . ?
C28 C27 C26 119.52(19) 2_457 . ?
C28 C27 H27 120.2 2_457 . ?
O4 C10 O3 120.4(2) . . ?
O4 C10 C9 122.6(2) . . ?
O3 C10 C9 116.9(2) . . ?
C15 C14 N2 119.5(2) . . ?
C19 C14 N2 119.7(2) . . ?
C19 C14 C15 120.8(2) . . ?
C16 C17 N3 120.3(2) . . ?
C18 C17 N3 119.5(2) . . ?
C18 C17 C16 120.1(2) . . ?
N1 C12 H12 125.0 . . ?
C13 C12 N1 110.1(2) . . ?
C13 C12 H12 125.0 . . ?
C3 C8 H8 119.4 . . ?
C7 C8 C3 121.2(2) . . ?
C7 C8 H8 119.4 . . ?
N6 C24 H24 127.1 . . ?
C23 C24 N6 105.8(2) . . ?
C23 C24 H24 127.1 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.4(2) . . ?
C16 C15 H15 120.3 . . ?
N3 C22 H22 123.7 . . ?
N4 C22 N3 112.5(3) . . ?
N4 C22 H22 123.7 . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C1 C2 C3 111.5(2) . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
O2 C1 C2 117.8(2) . . ?
O1 C1 O2 122.2(2) . . ?
O1 C1 C2 119.9(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.9(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.9(2) . . ?
C19 C18 H18 120.0 . . ?
C7 C6 H6 119.6 . . ?
C5 C6 C7 120.7(2) . . ?
C5 C6 H6 119.6 . . ?
N2 C13 H13 127.0 . . ?
C12 C13 N2 106.0(2) . . ?
C12 C13 H13 127.0 . . ?
N4 C21 H21 124.8 . . ?
C20 C21 N4 110.5(2) . . ?
C20 C21 H21 124.8 . . ?
C14 C19 C18 119.8(2) . . ?
C14 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C7 C9 C10 117.2(2) . . ?
C7 C9 H9A 108.0 . . ?
C7 C9 H9B 108.0 . . ?
C10 C9 H9A 108.0 . . ?
C10 C9 H9B 108.0 . . ?
H9A C9 H9B 107.2 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
N3 C20 H20 126.7 . . ?
C21 C20 N3 106.7(2) . . ?
C21 C20 H20 126.7 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_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 O4 C10 O3 -2.6(3) . . . . ?
Co1 O4 C10 C9 175.13(19) . . . . ?
Co1 O2 C1 O1 8.3(3) 1_665 . . . ?
Co1 O2 C1 C2 -169.65(17) 1_665 . . . ?
Co1 O3 C10 O4 2.5(2) . . . . ?
Co1 O3 C10 C9 -175.39(18) . . . . ?
Co1 N1 C11 N2 179.98(16) . . . . ?
Co1 N1 C12 C13 179.89(18) . . . . ?
Co1 N5 C25 N6 171.48(15) . . . . ?
Co1 N5 C23 C24 -172.17(17) . . . . ?
O4 C10 C9 C7 12.8(4) . . . . ?
O3 C10 C9 C7 -169.4(2) . . . . ?
N1 C12 C13 N2 0.3(3) . . . . ?
N5 C23 C24 N6 0.1(3) . . . . ?
N6 C26 C28 C27 179.49(18) . . . 2_457 ?
N6 C26 C27 C28 -179.49(18) . . . 2_457 ?
N3 C17 C16 C15 177.9(2) . . . . ?
N3 C17 C18 C19 -179.5(2) . . . . ?
N2 C14 C15 C16 -178.5(2) . . . . ?
N2 C14 C19 C18 176.8(2) . . . . ?
C11 N1 C12 C13 -0.3(3) . . . . ?
C11 N2 C14 C15 139.1(3) . . . . ?
C11 N2 C14 C19 -39.9(4) . . . . ?
C11 N2 C13 C12 -0.2(3) . . . . ?
C26 N6 C25 N5 -178.02(19) . . . . ?
C26 N6 C24 C23 178.3(2) . . . . ?
C25 N5 C23 C24 0.3(3) . . . . ?
C25 N6 C26 C28 31.3(3) . . . . ?
C25 N6 C26 C27 -149.3(2) . . . . ?
C25 N6 C24 C23 -0.5(3) . . . . ?
C3 C2 C1 O2 73.2(3) . . . . ?
C3 C2 C1 O1 -104.9(3) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C7 C6 C5 C4 1.7(4) . . . . ?
C28 C26 C27 C28 -0.1(3) . . . 2_457 ?
N4 C21 C20 N3 -0.6(4) . . . . ?
C23 N5 C25 N6 -0.7(3) . . . . ?
C27 C26 C28 C27 0.1(3) . . . 2_457 ?
C14 N2 C11 N1 -179.4(2) . . . . ?
C14 N2 C13 C12 179.3(2) . . . . ?
C14 C15 C16 C17 1.4(4) . . . . ?
C17 N3 C22 N4 178.7(3) . . . . ?
C17 N3 C20 C21 -179.3(2) . . . . ?
C17 C18 C19 C14 1.9(4) . . . . ?
C12 N1 C11 N2 0.2(3) . . . . ?
C8 C3 C2 C1 65.3(3) . . . . ?
C8 C3 C4 C5 -1.4(4) . . . . ?
C8 C7 C6 C5 -1.6(3) . . . . ?
C8 C7 C9 C10 81.0(3) . . . . ?
C24 N6 C26 C28 -147.3(2) . . . . ?
C24 N6 C26 C27 32.2(3) . . . . ?
C24 N6 C25 N5 0.8(3) . . . . ?
C15 C14 C19 C18 -2.2(4) . . . . ?
C22 N3 C17 C16 153.3(3) . . . . ?
C22 N3 C17 C18 -27.1(4) . . . . ?
C22 N3 C20 C21 1.7(3) . . . . ?
C22 N4 C21 C20 -0.7(4) . . . . ?
C2 C3 C8 C7 -178.83(19) . . . . ?
C2 C3 C4 C5 178.9(2) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C18 C17 C16 C15 -1.7(4) . . . . ?
C6 C7 C8 C3 0.0(3) . . . . ?
C6 C7 C9 C10 -100.7(3) . . . . ?
C13 N2 C11 N1 0.0(3) . . . . ?
C13 N2 C14 C15 -40.3(4) . . . . ?
C13 N2 C14 C19 140.7(3) . . . . ?
C21 N4 C22 N3 1.8(4) . . . . ?
C19 C14 C15 C16 0.5(4) . . . . ?
C9 C7 C8 C3 178.36(19) . . . . ?
C9 C7 C6 C5 -180.0(2) . . . . ?
C4 C3 C8 C7 1.5(3) . . . . ?
C4 C3 C2 C1 -115.1(3) . . . . ?
C20 N3 C17 C16 -25.5(4) . . . . ?
C20 N3 C17 C18 154.1(3) . . . . ?
C20 N3 C22 N4 -2.3(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_yd0714_0m
_database_code_depnum_ccdc_archive 'CCDC 1887627'
_audit_update_record             
;
2018-12-26 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;
_audit_creation_date             2018-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 N4 Ni O4, H2 O'
_chemical_formula_sum            'C22 H20 N4 Ni O5'
_chemical_formula_weight         479.11
_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 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3390 1.1120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.3304(16)
_cell_length_b                   17.4349(18)
_cell_length_c                   15.9678(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4267.9(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6272
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.620
_cell_measurement_theta_min      2.337
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.952
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0649 before and 0.0515 after correction. The Ratio of minimum to maximum transmission is 0.7640. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24546
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.255
_diffrn_reflns_theta_min         2.662
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3409
_reflns_number_total             5194
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+2.5546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1256
_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 O(H,H) groups
2.a Riding coordinates:
 O5(H5A,H5B)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Ni1 Ni 0.79593(2) 0.26350(2) 0.45085(2) 0.04315(13) Uani 1 1 d . . . . .
O1 O 0.70781(12) 0.28532(11) 0.34848(13) 0.0503(5) Uani 1 1 d . . . . .
O2 O 0.74503(13) 0.16887(11) 0.38700(13) 0.0513(5) Uani 1 1 d . . . . .
O3 O 0.65166(13) -0.12679(11) 0.46219(13) 0.0545(5) Uani 1 1 d . . . . .
O4 O 0.59873(13) -0.20557(13) 0.36831(14) 0.0573(5) Uani 1 1 d . . . . .
N1 N 0.69792(14) 0.27982(14) 0.53380(15) 0.0462(6) Uani 1 1 d . . . . .
N2 N 0.59565(14) 0.34623(13) 0.59741(15) 0.0424(5) Uani 1 1 d . . . . .
N3 N 0.54345(13) 0.61974(13) 0.59167(14) 0.0398(5) Uani 1 1 d . . . . .
N4 N 0.61960(15) 0.71136(14) 0.53141(15) 0.0458(6) Uani 1 1 d . . . . .
C1 C 0.70374(17) 0.21414(16) 0.33879(19) 0.0450(6) Uani 1 1 d . . . . .
C2 C 0.6489(2) 0.18299(18) 0.2676(2) 0.0618(9) Uani 1 1 d . . . . .
H2A H 0.589288 0.200179 0.275351 0.074 Uiso 1 1 calc R . . . .
H2B H 0.669928 0.205089 0.215584 0.074 Uiso 1 1 calc R . . . .
C3 C 0.64851(19) 0.09762(17) 0.25869(19) 0.0494(7) Uani 1 1 d . . . . .
C4 C 0.59947(18) 0.05198(18) 0.31174(19) 0.0506(7) Uani 1 1 d . . . . .
H4 H 0.563820 0.075402 0.351318 0.061 Uiso 1 1 calc R . . . .
C5 C 0.60163(17) -0.02694(18) 0.30794(18) 0.0475(7) Uani 1 1 d . . . . .
C6 C 0.54687(19) -0.0754(2) 0.3667(2) 0.0620(9) Uani 1 1 d . . . . .
H6A H 0.525435 -0.043863 0.412297 0.074 Uiso 1 1 calc R . . . .
H6B H 0.496999 -0.095870 0.336712 0.074 Uiso 1 1 calc R . . . .
C7 C 0.60078(18) -0.14019(19) 0.4011(2) 0.0529(8) Uani 1 1 d . . . . .
C8 C 0.6541(2) -0.06129(18) 0.2491(2) 0.0587(8) Uani 1 1 d . . . . .
H8 H 0.657916 -0.114479 0.246623 0.070 Uiso 1 1 calc R . . . .
C9 C 0.7009(2) -0.0172(2) 0.1940(2) 0.0755(11) Uani 1 1 d . . . . .
H9 H 0.734894 -0.040780 0.153190 0.091 Uiso 1 1 calc R . . . .
C10 C 0.6980(2) 0.0619(2) 0.1986(2) 0.0639(9) Uani 1 1 d . . . . .
H10 H 0.729897 0.091167 0.160724 0.077 Uiso 1 1 calc R . . . .
C11 C 0.65586(17) 0.34500(16) 0.53603(17) 0.0420(6) Uani 1 1 d . . . . .
H11 H 0.666271 0.385612 0.499622 0.050 Uiso 1 1 calc R . . . .
C12 C 0.5997(2) 0.27672(19) 0.6363(3) 0.0718(11) Uani 1 1 d . . . . .
H12 H 0.566115 0.260218 0.681363 0.086 Uiso 1 1 calc R . . . .
C13 C 0.6620(2) 0.23690(19) 0.5961(3) 0.0714(11) Uani 1 1 d . . . . .
H13 H 0.678400 0.186934 0.609125 0.086 Uiso 1 1 calc R . . . .
C14 C 0.53967(16) 0.40932(15) 0.61594(16) 0.0382(6) Uani 1 1 d . . . . .
C15 C 0.56890(16) 0.48283(15) 0.59875(16) 0.0391(6) Uani 1 1 d . . . . .
H15 H 0.624649 0.490521 0.577380 0.047 Uiso 1 1 calc R . . . .
C16 C 0.51460(16) 0.54470(15) 0.61359(16) 0.0394(6) Uani 1 1 d . . . . .
C17 C 0.61352(17) 0.63741(16) 0.54409(18) 0.0434(6) Uani 1 1 d . . . . .
H17 H 0.652581 0.601466 0.522971 0.052 Uiso 1 1 calc R . . . .
C18 C 0.5503(2) 0.74305(17) 0.5719(2) 0.0573(8) Uani 1 1 d . . . . .
H18 H 0.537668 0.795210 0.573459 0.069 Uiso 1 1 calc R . . . .
C19 C 0.5028(2) 0.68825(17) 0.6094(2) 0.0574(8) Uani 1 1 d . . . . .
H19 H 0.452466 0.695168 0.640949 0.069 Uiso 1 1 calc R . . . .
C20 C 0.43251(17) 0.53325(18) 0.64883(18) 0.0480(7) Uani 1 1 d . . . . .
H20 H 0.396342 0.574755 0.660337 0.058 Uiso 1 1 calc R . . . .
C21 C 0.40567(17) 0.45967(18) 0.66638(19) 0.0505(7) Uani 1 1 d . . . . .
H21 H 0.350882 0.452144 0.689995 0.061 Uiso 1 1 calc R . . . .
C22 C 0.45738(17) 0.39679(17) 0.65008(18) 0.0462(7) Uani 1 1 d . . . . .
H22 H 0.437851 0.347399 0.661553 0.055 Uiso 1 1 calc R . . . .
O5 O 0.73925(16) 0.01958(15) 0.48172(16) 0.0788(8) Uani 1 1 d . . . . .
H5A H 0.709397 -0.020084 0.470068 0.118 Uiso 1 1 d R . . . .
H5B H 0.722737 0.052886 0.446178 0.118 Uiso 1 1 d R . . . .


_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 O1 2.154(2) . ?
Ni1 O2 2.091(2) . ?
Ni1 O3 2.083(2) 8_765 ?
Ni1 O4 2.153(2) 8_765 ?
Ni1 N1 2.023(2) . ?
Ni1 N4 2.039(2) 8_755 ?
Ni1 C1 2.437(3) . ?
Ni1 C7 2.441(3) 8_765 ?
O1 C1 1.252(4) . ?
O2 C1 1.271(3) . ?
O3 C7 1.270(4) . ?
O4 C7 1.255(4) . ?
N1 C11 1.307(4) . ?
N1 C13 1.361(4) . ?
N2 C11 1.347(3) . ?
N2 C12 1.363(4) . ?
N2 C14 1.426(3) . ?
N3 C16 1.425(3) . ?
N3 C17 1.351(3) . ?
N3 C19 1.376(3) . ?
N4 C17 1.308(4) . ?
N4 C18 1.361(4) . ?
C1 C2 1.515(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.495(4) . ?
C3 C4 1.384(4) . ?
C3 C10 1.373(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(4) . ?
C5 C6 1.516(4) . ?
C5 C8 1.375(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.504(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.370(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.345(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(4) . ?
C14 C22 1.392(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(4) . ?
C16 C20 1.393(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.342(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.376(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(4) . ?
C22 H22 0.9300 . ?
O5 H5A 0.8498 . ?
O5 H5B 0.8505 . ?

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 Ni1 C1 30.87(8) . . ?
O1 Ni1 C7 92.21(9) . 8_765 ?
O2 Ni1 O1 62.31(7) . . ?
O2 Ni1 O4 100.32(9) . 8_765 ?
O2 Ni1 C1 31.44(8) . . ?
O2 Ni1 C7 128.79(10) . 8_765 ?
O3 Ni1 O1 98.38(8) 8_765 . ?
O3 Ni1 O2 155.68(8) 8_765 . ?
O3 Ni1 O4 62.21(8) 8_765 8_765 ?
O3 Ni1 C1 127.73(9) 8_765 . ?
O3 Ni1 C7 31.36(10) 8_765 8_765 ?
O4 Ni1 O1 87.80(8) 8_765 . ?
O4 Ni1 C1 94.24(9) 8_765 . ?
O4 Ni1 C7 30.90(9) 8_765 8_765 ?
N1 Ni1 O1 90.35(9) . . ?
N1 Ni1 O2 98.80(9) . . ?
N1 Ni1 O3 95.77(9) . 8_765 ?
N1 Ni1 O4 157.30(10) . 8_765 ?
N1 Ni1 N4 96.97(10) . 8_755 ?
N1 Ni1 C1 95.72(10) . . ?
N1 Ni1 C7 126.73(11) . 8_765 ?
N4 Ni1 O1 162.85(9) 8_755 . ?
N4 Ni1 O2 101.12(8) 8_755 . ?
N4 Ni1 O3 96.29(9) 8_755 8_765 ?
N4 Ni1 O4 91.23(9) 8_755 8_765 ?
N4 Ni1 C1 132.38(10) 8_755 . ?
N4 Ni1 C7 95.73(10) 8_755 8_765 ?
C1 Ni1 C7 112.35(10) . 8_765 ?
C1 O1 Ni1 87.14(16) . . ?
C1 O2 Ni1 89.49(17) . . ?
C7 O3 Ni1 90.07(18) . 8_755 ?
C7 O4 Ni1 87.31(18) . 8_755 ?
C11 N1 Ni1 120.43(19) . . ?
C11 N1 C13 105.0(2) . . ?
C13 N1 Ni1 134.5(2) . . ?
C11 N2 C12 106.7(2) . . ?
C11 N2 C14 125.2(2) . . ?
C12 N2 C14 128.2(2) . . ?
C17 N3 C16 126.5(2) . . ?
C17 N3 C19 106.1(2) . . ?
C19 N3 C16 127.3(2) . . ?
C17 N4 Ni1 125.60(19) . 8_765 ?
C17 N4 C18 105.7(2) . . ?
C18 N4 Ni1 127.9(2) . 8_765 ?
O1 C1 Ni1 61.99(15) . . ?
O1 C1 O2 121.0(3) . . ?
O1 C1 C2 118.4(2) . . ?
O2 C1 Ni1 59.07(15) . . ?
O2 C1 C2 120.5(3) . . ?
C2 C1 Ni1 178.2(2) . . ?
C1 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 C1 115.5(2) . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C4 C3 C2 121.1(3) . . ?
C10 C3 C2 121.0(3) . . ?
C10 C3 C4 117.9(3) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 C3 122.3(3) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C6 121.1(3) . . ?
C8 C5 C4 118.6(3) . . ?
C8 C5 C6 120.3(3) . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 C5 109.9(2) . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
O3 C7 Ni1 58.56(15) . 8_755 ?
O3 C7 C6 118.7(3) . . ?
O4 C7 Ni1 61.78(16) . 8_755 ?
O4 C7 O3 120.2(3) . . ?
O4 C7 C6 121.0(3) . . ?
C6 C7 Ni1 172.9(2) . 8_755 ?
C5 C8 H8 120.0 . . ?
C9 C8 C5 120.1(3) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C3 C10 C9 120.5(3) . . ?
C3 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
N1 C11 N2 111.8(2) . . ?
N1 C11 H11 124.1 . . ?
N2 C11 H11 124.1 . . ?
N2 C12 H12 127.1 . . ?
C13 C12 N2 105.9(3) . . ?
C13 C12 H12 127.1 . . ?
N1 C13 H13 124.7 . . ?
C12 C13 N1 110.6(3) . . ?
C12 C13 H13 124.7 . . ?
C15 C14 N2 118.5(2) . . ?
C15 C14 C22 121.1(3) . . ?
C22 C14 N2 120.4(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.5(2) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 N3 119.2(2) . . ?
C15 C16 C20 120.1(2) . . ?
C20 C16 N3 120.8(2) . . ?
N3 C17 H17 124.2 . . ?
N4 C17 N3 111.6(2) . . ?
N4 C17 H17 124.2 . . ?
N4 C18 H18 124.9 . . ?
C19 C18 N4 110.2(3) . . ?
C19 C18 H18 124.9 . . ?
N3 C19 H19 126.8 . . ?
C18 C19 N3 106.3(3) . . ?
C18 C19 H19 126.8 . . ?
C16 C20 H20 120.5 . . ?
C21 C20 C16 119.1(3) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 H21 119.0 . . ?
C20 C21 C22 122.1(3) . . ?
C22 C21 H21 119.0 . . ?
C14 C22 H22 121.0 . . ?
C21 C22 C14 118.1(3) . . ?
C21 C22 H22 121.0 . . ?
H5A O5 H5B 104.4 . . ?

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
Ni1 O1 C1 O2 1.4(3) . . . . ?
Ni1 O1 C1 C2 -178.1(3) . . . . ?
Ni1 O2 C1 O1 -1.4(3) . . . . ?
Ni1 O2 C1 C2 178.0(3) . . . . ?
Ni1 O3 C7 O4 4.6(3) 8_755 . . . ?
Ni1 O3 C7 C6 -172.4(2) 8_755 . . . ?
Ni1 O4 C7 O3 -4.5(3) 8_755 . . . ?
Ni1 O4 C7 C6 172.5(3) 8_755 . . . ?
Ni1 N1 C11 N2 -177.37(18) . . . . ?
Ni1 N1 C13 C12 176.9(3) . . . . ?
Ni1 N4 C17 N3 -171.06(18) 8_765 . . . ?
Ni1 N4 C18 C19 170.7(2) 8_765 . . . ?
O1 C1 C2 C3 178.8(3) . . . . ?
O2 C1 C2 C3 -0.7(4) . . . . ?
N2 C12 C13 N1 0.7(5) . . . . ?
N2 C14 C15 C16 177.8(2) . . . . ?
N2 C14 C22 C21 -179.6(3) . . . . ?
N3 C16 C20 C21 177.7(3) . . . . ?
N4 C18 C19 N3 -0.1(4) . . . . ?
C1 C2 C3 C4 77.0(4) . . . . ?
C1 C2 C3 C10 -101.8(4) . . . . ?
C2 C3 C4 C5 -176.3(3) . . . . ?
C2 C3 C10 C9 176.4(3) . . . . ?
C3 C4 C5 C6 -179.7(3) . . . . ?
C3 C4 C5 C8 -0.3(4) . . . . ?
C4 C3 C10 C9 -2.5(5) . . . . ?
C4 C5 C6 C7 -135.2(3) . . . . ?
C4 C5 C8 C9 -2.0(5) . . . . ?
C5 C6 C7 O3 80.9(4) . . . . ?
C5 C6 C7 O4 -96.1(3) . . . . ?
C5 C8 C9 C10 2.0(6) . . . . ?
C6 C5 C8 C9 177.5(3) . . . . ?
C8 C5 C6 C7 45.3(4) . . . . ?
C8 C9 C10 C3 0.3(6) . . . . ?
C10 C3 C4 C5 2.5(4) . . . . ?
C11 N1 C13 C12 -0.9(4) . . . . ?
C11 N2 C12 C13 -0.2(4) . . . . ?
C11 N2 C14 C15 -29.3(4) . . . . ?
C11 N2 C14 C22 150.3(3) . . . . ?
C12 N2 C11 N1 -0.4(4) . . . . ?
C12 N2 C14 C15 150.8(3) . . . . ?
C12 N2 C14 C22 -29.5(4) . . . . ?
C13 N1 C11 N2 0.8(4) . . . . ?
C14 N2 C11 N1 179.7(2) . . . . ?
C14 N2 C12 C13 179.7(3) . . . . ?
C14 C15 C16 N3 -176.8(2) . . . . ?
C14 C15 C16 C20 2.7(4) . . . . ?
C15 C14 C22 C21 0.0(4) . . . . ?
C15 C16 C20 C21 -1.7(4) . . . . ?
C16 N3 C17 N4 176.3(2) . . . . ?
C16 N3 C19 C18 -176.0(3) . . . . ?
C16 C20 C21 C22 -0.1(5) . . . . ?
C17 N3 C16 C15 12.2(4) . . . . ?
C17 N3 C16 C20 -167.2(3) . . . . ?
C17 N3 C19 C18 -0.1(4) . . . . ?
C17 N4 C18 C19 0.3(4) . . . . ?
C18 N4 C17 N3 -0.4(3) . . . . ?
C19 N3 C16 C15 -172.8(3) . . . . ?
C19 N3 C16 C20 7.8(4) . . . . ?
C19 N3 C17 N4 0.3(3) . . . . ?
C20 C21 C22 C14 1.0(4) . . . . ?
C22 C14 C15 C16 -1.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
