# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_xb0953
_database_code_depnum_ccdc_archive 'CCDC 2189569'
loop_
_audit_author_name
_audit_author_address
'yan yang tian '
;Xian Polytechnic University
China
;
_audit_update_record             
;
2022-09-19 deposited with the CCDC.	2022-09-20 downloaded from the CCDC.
;
_audit_creation_date             2022-09-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H17 N Ni O13'
_chemical_formula_sum            'C22 H17 N Ni O13'
_chemical_formula_weight         562.07
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   7.8514(8)
_cell_length_b                   22.467(2)
_cell_length_c                   12.0991(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2134.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2645
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.54
_cell_measurement_theta_min      3.09
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.743
_exptl_absorpt_coefficient_mu    0.989
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0716 before and 0.0436 after correction.
The Ratio of minimum to maximum transmission is 0.9225.
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    1.749
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11338
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.867
_diffrn_reflns_theta_min         1.813
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1874
_reflns_number_total             2345
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.6836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0888
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1(H1)
2.b Rotating group:
 O7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C10(H10), C12(H12)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 -0.24919(4) -0.250000 1.23858(3) 0.01739(12) Uani 1 2 d S T P . .
O1 O -0.0069(2) -0.250000 1.31580(16) 0.0187(4) Uani 1 2 d S T P . .
H1 H -0.004707 -0.280380 1.357230 0.028 Uiso 1 1 d R U . . .
O2 O -0.16782(17) -0.31202(6) 1.12571(12) 0.0220(3) Uani 1 1 d . . . . .
O3 O -0.42298(19) -0.34945(6) 1.08592(13) 0.0306(4) Uani 1 1 d . . . . .
O4 O -0.3587(2) -0.55978(7) 0.96181(16) 0.0472(5) Uani 1 1 d . . . . .
H4 H -0.407747 -0.590709 0.945060 0.071 Uiso 1 1 calc R U . . .
O5 O -0.2417(2) -0.57074(7) 0.79505(18) 0.0492(5) Uani 1 1 d . . . . .
O6 O 0.5359(2) -0.29763(8) 0.86180(17) 0.0459(5) Uani 1 1 d . . . . .
O7 O -0.31752(19) -0.18555(6) 1.34700(12) 0.0262(3) Uani 1 1 d . . . . .
H7A H -0.302121 -0.151606 1.317451 0.039 Uiso 1 1 d R U . . .
H7B H -0.424373 -0.187336 1.358199 0.039 Uiso 1 1 d R U . . .
N1 N 0.4625(3) -0.250000 0.8686(2) 0.0279(6) Uani 1 2 d S T P . .
C1 C -0.2649(2) -0.34601(9) 1.07089(17) 0.0212(4) Uani 1 1 d . . . . .
C2 C -0.1884(3) -0.38408(9) 0.98133(17) 0.0217(4) Uani 1 1 d . . . . .
C3 C -0.2484(3) -0.44224(9) 0.9735(2) 0.0278(5) Uani 1 1 d . . . . .
H3 H -0.326504 -0.455826 1.025529 0.033 Uiso 1 1 calc R U . . .
C4 C -0.1954(3) -0.48040(10) 0.8907(2) 0.0302(5) Uani 1 1 d . . . . .
C5 C -0.2658(3) -0.54143(10) 0.8775(2) 0.0348(6) Uani 1 1 d . . . . .
C6 C -0.0783(3) -0.46000(10) 0.8134(2) 0.0384(6) Uani 1 1 d . . . . .
H6 H -0.042958 -0.484823 0.756356 0.046 Uiso 1 1 calc R U . . .
C7 C -0.0147(3) -0.40317(10) 0.8212(2) 0.0348(6) Uani 1 1 d . . . . .
H7 H 0.064520 -0.390326 0.769278 0.042 Uiso 1 1 calc R U . . .
C8 C -0.0657(3) -0.36392(9) 0.90522(18) 0.0237(4) Uani 1 1 d . . . . .
C9 C 0.0185(2) -0.30433(9) 0.90571(17) 0.0218(4) Uani 1 1 d . . . . .
C10 C 0.1947(3) -0.30381(9) 0.89161(18) 0.0252(5) Uani 1 1 d . . . . .
H10 H 0.255239 -0.339298 0.887063 0.030 Uiso 1 1 calc R U . . .
C11 C 0.2776(3) -0.250000 0.8845(2) 0.0238(6) Uani 1 2 d S T P . .
C12 C -0.0678(4) -0.250000 0.9134(2) 0.0223(6) Uani 1 2 d S T P . .
H12 H -0.185169 -0.250000 0.923807 0.027 Uiso 1 2 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 2.1276(17) 6_558 ?
Ni1 O1 2.1195(17) . ?
Ni1 O2 2.0530(14) . ?
Ni1 O2 2.0530(14) 8 ?
Ni1 O7 2.0263(14) 8 ?
Ni1 O7 2.0263(14) . ?
O1 H1 0.8470 . ?
O1 H1 0.8470 8 ?
O2 C1 1.266(2) . ?
O3 C1 1.257(2) . ?
O4 H4 0.8200 . ?
O4 C5 1.320(3) . ?
O5 C5 1.210(3) . ?
O6 N1 1.218(2) . ?
O7 H7A 0.8508 . ?
O7 H7B 0.8507 . ?
N1 C11 1.465(4) . ?
C1 C2 1.506(3) . ?
C2 C3 1.392(3) . ?
C2 C8 1.407(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(3) . ?
C4 C5 1.487(3) . ?
C4 C6 1.389(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.374(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.404(3) . ?
C8 C9 1.493(3) . ?
C9 C10 1.393(3) . ?
C9 C12 1.399(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(2) . ?
C12 H12 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 Ni1 O1 171.85(4) . 6_558 ?
O2 Ni1 O1 95.18(6) . 6_558 ?
O2 Ni1 O1 95.18(6) 8 6_558 ?
O2 Ni1 O1 90.80(6) . . ?
O2 Ni1 O1 90.80(6) 8 . ?
O2 Ni1 O2 85.50(8) . 8 ?
O7 Ni1 O1 87.26(6) 8 . ?
O7 Ni1 O1 87.04(6) . 6_558 ?
O7 Ni1 O1 87.26(6) . . ?
O7 Ni1 O1 87.04(6) 8 6_558 ?
O7 Ni1 O2 176.49(6) 8 8 ?
O7 Ni1 O2 176.49(6) . . ?
O7 Ni1 O2 91.60(6) . 8 ?
O7 Ni1 O2 91.60(6) 8 . ?
O7 Ni1 O7 91.23(9) . 8 ?
Ni1 O1 Ni1 135.83(10) . 6_658 ?
Ni1 O1 H1 99.43(3) 6_658 8 ?
Ni1 O1 H1 106.20(3) . 8 ?
Ni1 O1 H1 99.4 6_658 . ?
Ni1 O1 H1 106.2 . . ?
H1 O1 H1 107.4 . 8 ?
C1 O2 Ni1 124.77(12) . . ?
C5 O4 H4 109.5 . . ?
Ni1 O7 H7A 109.3 . . ?
Ni1 O7 H7B 109.3 . . ?
H7A O7 H7B 104.4 . . ?
O6 N1 O6 123.0(3) . 8 ?
O6 N1 C11 118.52(13) . . ?
O6 N1 C11 118.52(13) 8 . ?
O2 C1 C2 118.65(17) . . ?
O3 C1 O2 123.76(18) . . ?
O3 C1 C2 117.59(18) . . ?
C3 C2 C1 116.55(18) . . ?
C3 C2 C8 119.30(19) . . ?
C8 C2 C1 124.13(17) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 122.5(2) . . ?
C3 C4 C6 118.9(2) . . ?
C6 C4 C5 118.6(2) . . ?
O4 C5 C4 114.2(2) . . ?
O5 C5 O4 123.6(2) . . ?
O5 C5 C4 122.1(2) . . ?
C4 C6 H6 120.0 . . ?
C7 C6 C4 120.1(2) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.0 . . ?
C6 C7 C8 122.0(2) . . ?
C8 C7 H7 119.0 . . ?
C2 C8 C9 126.09(18) . . ?
C7 C8 C2 117.83(19) . . ?
C7 C8 C9 116.08(19) . . ?
C10 C9 C8 116.53(18) . . ?
C10 C9 C12 118.8(2) . . ?
C12 C9 C8 124.60(19) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 N1 118.50(13) . . ?
C10 C11 N1 118.50(13) 8 . ?
C10 C11 C10 123.0(3) . 8 ?
C9 C12 C9 121.5(3) 8 . ?
C9 C12 H12 119.3 8 . ?
C9 C12 H12 119.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 0.85 1.81 2.6154(17) 157.0 6_658 yes
O4 H4 O3 0.82 1.93 2.726(2) 164.4 5_447 yes
O7 H7A O5 0.85 1.87 2.695(2) 163.4 7_566 yes
O7 H7B O2 0.85 1.92 2.771(2) 175.9 3_447 yes

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 O2 C1 O3 -6.4(3) . . . . ?
Ni1 O2 C1 C2 172.76(13) . . . . ?
O2 C1 C2 C3 138.8(2) . . . . ?
O2 C1 C2 C8 -42.9(3) . . . . ?
O3 C1 C2 C3 -42.0(3) . . . . ?
O3 C1 C2 C8 136.3(2) . . . . ?
O6 N1 C11 C10 -179.7(2) . . . 8 ?
O6 N1 C11 C10 -0.2(4) 8 . . 8 ?
O6 N1 C11 C10 0.2(4) . . . . ?
O6 N1 C11 C10 179.7(2) 8 . . . ?
C1 C2 C3 C4 176.2(2) . . . . ?
C1 C2 C8 C7 -175.5(2) . . . . ?
C1 C2 C8 C9 5.3(3) . . . . ?
C2 C3 C4 C5 -176.4(2) . . . . ?
C2 C3 C4 C6 0.2(4) . . . . ?
C2 C8 C9 C10 133.6(2) . . . . ?
C2 C8 C9 C12 -49.9(3) . . . . ?
C3 C2 C8 C7 2.7(3) . . . . ?
C3 C2 C8 C9 -176.5(2) . . . . ?
C3 C4 C5 O4 -11.6(3) . . . . ?
C3 C4 C5 O5 167.0(2) . . . . ?
C3 C4 C6 C7 1.3(4) . . . . ?
C4 C6 C7 C8 -0.7(4) . . . . ?
C5 C4 C6 C7 178.0(2) . . . . ?
C6 C4 C5 O4 171.8(2) . . . . ?
C6 C4 C5 O5 -9.6(4) . . . . ?
C6 C7 C8 C2 -1.3(4) . . . . ?
C6 C7 C8 C9 177.9(2) . . . . ?
C7 C8 C9 C10 -45.5(3) . . . . ?
C7 C8 C9 C12 130.9(2) . . . . ?
C8 C2 C3 C4 -2.2(3) . . . . ?
C8 C9 C10 C11 176.0(2) . . . . ?
C8 C9 C12 C9 -175.54(16) . . . 8 ?
C9 C10 C11 N1 -179.4(2) . . . . ?
C9 C10 C11 C10 0.5(5) . . . 8 ?
C10 C9 C12 C9 0.9(4) . . . 8 ?
C12 C9 C10 C11 -0.7(3) . . . . ?

_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_xb0954_0m
_database_code_depnum_ccdc_archive 'CCDC 2189570'
loop_
_audit_author_name
_audit_author_address
'yan yang tian '
;Xian Polytechnic University
China
;
_audit_update_record             
;
2022-09-19 deposited with the CCDC.	2022-09-20 downloaded from the CCDC.
;
_audit_creation_date             2022-09-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H17 Co N O13'
_chemical_formula_sum            'C22 H17 Co N O13'
_chemical_formula_weight         562.29
_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'
Co Co 0.3490 0.9720 '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'
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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   7.9535(7)
_cell_length_b                   22.571(2)
_cell_length_c                   12.0560(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2164.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3526
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.778
_cell_measurement_theta_min      3.068
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0609 before and 0.0400 after correction.
The Ratio of minimum to maximum transmission is 0.8562.
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    1.726
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1148
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11649
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.295
_diffrn_reflns_theta_min         1.915
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2089
_reflns_number_total             2468
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2468
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.077
_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)+(0.0420P)²+0.6359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0826
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1(H1)
2.b Rotating group:
 O7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C10(H10), C12(H12)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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
Co1 Co 0.75653(4) 0.250000 0.26094(3) 0.01790(11) Uani 1 2 d S T P . .
O1 O 0.51592(18) 0.250000 0.17957(13) 0.0203(4) Uani 1 2 d S T P . .
H1 H 0.520844 0.220200 0.138907 0.030 Uiso 1 1 d R U . . .
O2 O 0.67435(15) 0.31233(5) 0.37609(10) 0.0232(3) Uani 1 1 d . . . . .
O3 O 0.92607(16) 0.35017(6) 0.41455(11) 0.0309(3) Uani 1 1 d . . . . .
O4 O 0.8599(2) 0.55902(7) 0.53995(14) 0.0499(4) Uani 1 1 d . . . . .
H4 H 0.908370 0.589846 0.556541 0.075 Uiso 1 1 calc R U . . .
O5 O 0.7420(2) 0.57068(7) 0.70651(16) 0.0511(5) Uani 1 1 d . . . . .
O6 O -0.01980(17) 0.20252(7) 0.63463(15) 0.0487(4) Uani 1 1 d . . . . .
O7 O 0.83063(15) 0.18415(5) 0.15356(10) 0.0270(3) Uani 1 1 d . . . . .
H7A H 0.809704 0.149227 0.181222 0.041 Uiso 1 1 d R U . . .
H7B H 0.938251 0.186428 0.140710 0.041 Uiso 1 1 d R U . . .
N1 N 0.0521(3) 0.250000 0.62854(17) 0.0285(5) Uani 1 2 d S T P . .
C1 C 0.7710(2) 0.34638(7) 0.43105(14) 0.0212(4) Uani 1 1 d . . . . .
C2 C 0.6954(2) 0.38392(7) 0.52141(15) 0.0232(4) Uani 1 1 d . . . . .
C3 C 0.7542(2) 0.44213(8) 0.52891(17) 0.0289(4) Uani 1 1 d . . . . .
H3 H 0.830906 0.455914 0.476728 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7005(2) 0.47965(8) 0.61249(18) 0.0317(4) Uani 1 1 d . . . . .
C5 C 0.7677(2) 0.54101(9) 0.62463(19) 0.0351(5) Uani 1 1 d . . . . .
C6 C 0.5864(3) 0.45916(9) 0.69021(18) 0.0397(5) Uani 1 1 d . . . . .
H6 H 0.551801 0.483727 0.747778 0.048 Uiso 1 1 calc R U . . .
C7 C 0.5241(3) 0.40243(9) 0.68232(17) 0.0358(5) Uani 1 1 d . . . . .
H7 H 0.445939 0.389504 0.734360 0.043 Uiso 1 1 calc R U . . .
C8 C 0.5751(2) 0.36356(8) 0.59798(15) 0.0249(4) Uani 1 1 d . . . . .
C9 C 0.4927(2) 0.30393(8) 0.59682(14) 0.0225(4) Uani 1 1 d . . . . .
C10 C 0.3182(2) 0.30355(8) 0.60926(15) 0.0257(4) Uani 1 1 d . . . . .
H10 H 0.258533 0.338906 0.613336 0.031 Uiso 1 1 calc R U . . .
C11 C 0.2360(3) 0.250000 0.6154(2) 0.0232(5) Uani 1 2 d S T P . .
C12 C 0.5783(3) 0.250000 0.59003(19) 0.0222(5) Uani 1 2 d S T P . .
H12 H 0.694415 0.250001 0.580827 0.027 Uiso 1 2 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.1842(15) 6_656 ?
Co1 O1 2.1505(15) . ?
Co1 O2 2.0819(12) . ?
Co1 O2 2.0819(12) 8_565 ?
Co1 O7 2.0573(12) 8_565 ?
Co1 O7 2.0573(12) . ?
O1 H1 0.8332 . ?
O1 H1 0.8332 8_565 ?
O2 C1 1.273(2) . ?
O3 C1 1.252(2) . ?
O4 H4 0.8200 . ?
O4 C5 1.321(3) . ?
O5 C5 1.210(3) . ?
O6 N1 1.2168(18) . ?
O7 H7A 0.8719 . ?
O7 H7B 0.8714 . ?
N1 C11 1.471(3) . ?
C1 C2 1.505(2) . ?
C2 C3 1.397(2) . ?
C2 C8 1.407(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(3) . ?
C4 C5 1.492(3) . ?
C4 C6 1.384(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.403(3) . ?
C8 C9 1.497(2) . ?
C9 C10 1.395(2) . ?
C9 C12 1.397(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(2) . ?
C12 H12 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 O1 172.03(3) . 6_656 ?
O2 Co1 O1 94.45(5) . 6_656 ?
O2 Co1 O1 94.45(5) 8_565 6_656 ?
O2 Co1 O1 91.42(5) . . ?
O2 Co1 O1 91.42(5) 8_565 . ?
O2 Co1 O2 85.04(7) . 8_565 ?
O7 Co1 O1 88.16(5) 8_565 . ?
O7 Co1 O1 86.33(5) . 6_656 ?
O7 Co1 O1 88.16(5) . . ?
O7 Co1 O1 86.33(5) 8_565 6_656 ?
O7 Co1 O2 176.22(5) 8_565 8_565 ?
O7 Co1 O2 176.22(5) . . ?
O7 Co1 O2 91.22(5) . 8_565 ?
O7 Co1 O2 91.22(5) 8_565 . ?
O7 Co1 O7 92.52(7) . 8_565 ?
Co1 O1 Co1 133.69(8) . 6_556 ?
Co1 O1 H1 103.74(2) 6_556 8_565 ?
Co1 O1 H1 103.10(2) . 8_565 ?
Co1 O1 H1 103.7 6_556 . ?
Co1 O1 H1 103.1 . . ?
H1 O1 H1 107.7 . 8_565 ?
C1 O2 Co1 124.43(11) . . ?
C5 O4 H4 109.5 . . ?
Co1 O7 H7A 111.0 . . ?
Co1 O7 H7B 110.5 . . ?
H7A O7 H7B 108.0 . . ?
O6 N1 O6 123.5(2) 8_565 . ?
O6 N1 C11 118.26(12) 8_565 . ?
O6 N1 C11 118.26(12) . . ?
O2 C1 C2 118.37(15) . . ?
O3 C1 O2 123.60(16) . . ?
O3 C1 C2 118.03(15) . . ?
C3 C2 C1 116.25(16) . . ?
C3 C2 C8 119.49(16) . . ?
C8 C2 C1 124.24(15) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.28(18) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 121.92(18) . . ?
C3 C4 C6 119.40(18) . . ?
C6 C4 C5 118.62(18) . . ?
O4 C5 C4 114.14(17) . . ?
O5 C5 O4 123.62(19) . . ?
O5 C5 C4 122.2(2) . . ?
C4 C6 H6 120.0 . . ?
C7 C6 C4 120.02(18) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.85(18) . . ?
C8 C7 H7 119.1 . . ?
C2 C8 C9 125.84(15) . . ?
C7 C8 C2 117.91(16) . . ?
C7 C8 C9 116.24(16) . . ?
C10 C9 C8 116.10(16) . . ?
C10 C9 C12 119.05(17) . . ?
C12 C9 C8 124.76(15) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 118.94(17) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 N1 118.58(11) . . ?
C10 C11 N1 118.58(11) 8_565 . ?
C10 C11 C10 122.8(2) . 8_565 ?
C9 C12 C9 121.2(2) . 8_565 ?
C9 C12 H12 119.4 . . ?
C9 C12 H12 119.4 8_565 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 0.83 1.87 2.6287(15) 150.3 3_455 yes
O4 H4 O3 0.82 1.92 2.7200(19) 164.7 5_766 yes
O7 H7A O5 0.87 1.85 2.702(2) 167.0 7_755 yes
O7 H7B O2 0.87 1.89 2.7582(18) 175.2 3 yes

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 7.0(2) . . . . ?
Co1 O2 C1 C2 -172.60(11) . . . . ?
O2 C1 C2 C3 -138.73(17) . . . . ?
O2 C1 C2 C8 42.8(3) . . . . ?
O3 C1 C2 C3 41.7(2) . . . . ?
O3 C1 C2 C8 -136.82(18) . . . . ?
O6 N1 C11 C10 179.5(2) 8_565 . . 8_565 ?
O6 N1 C11 C10 0.8(3) . . . 8_565 ?
O6 N1 C11 C10 -0.8(3) 8_565 . . . ?
O6 N1 C11 C10 -179.5(2) . . . . ?
C1 C2 C3 C4 -176.43(17) . . . . ?
C1 C2 C8 C7 175.84(17) . . . . ?
C1 C2 C8 C9 -5.4(3) . . . . ?
C2 C3 C4 C5 177.22(18) . . . . ?
C2 C3 C4 C6 0.0(3) . . . . ?
C2 C8 C9 C10 -132.43(19) . . . . ?
C2 C8 C9 C12 51.0(3) . . . . ?
C3 C2 C8 C7 -2.6(3) . . . . ?
C3 C2 C8 C9 176.14(17) . . . . ?
C3 C4 C5 O4 10.3(3) . . . . ?
C3 C4 C5 O5 -168.1(2) . . . . ?
C3 C4 C6 C7 -1.7(3) . . . . ?
C4 C6 C7 C8 1.2(3) . . . . ?
C5 C4 C6 C7 -179.0(2) . . . . ?
C6 C4 C5 O4 -172.5(2) . . . . ?
C6 C4 C5 O5 9.1(3) . . . . ?
C6 C7 C8 C2 1.0(3) . . . . ?
C6 C7 C8 C9 -177.86(19) . . . . ?
C7 C8 C9 C10 46.3(2) . . . . ?
C7 C8 C9 C12 -130.3(2) . . . . ?
C8 C2 C3 C4 2.1(3) . . . . ?
C8 C9 C10 C11 -176.25(17) . . . . ?
C8 C9 C12 C9 175.71(13) . . . 8_565 ?
C9 C10 C11 N1 179.98(18) . . . . ?
C9 C10 C11 C10 -0.3(4) . . . 8_565 ?
C10 C9 C12 C9 -0.8(3) . . . 8_565 ?
C12 C9 C10 C11 0.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
