# 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 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zhhl_21_1
_database_code_depnum_ccdc_archive 'CCDC 1869621'
loop_
_audit_author_name
_audit_author_address
'lan qin Chai'
;Lanzhou Jiaotong University
China
;
_audit_update_record             
;
2018-09-25 deposited with the CCDC.	2019-07-04 downloaded from the CCDC.
;
_audit_creation_date             2018-05-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H30 Co N4 O6, N O3'
_chemical_formula_sum            'C32 H30 Co N5 O9'
_chemical_formula_weight         687.54
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.4517(5)
_cell_length_b                   11.3315(3)
_cell_length_c                   14.6402(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.439(2)
_cell_angle_gamma                90
_cell_volume                     3051.86(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3217
_cell_measurement_temperature    294.55(10)
_cell_measurement_theta_max      27.8530
_cell_measurement_theta_min      3.5960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98045
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11901
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.322
_diffrn_ambient_temperature      294.55(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -101.00  -74.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0367  178.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -33.00   47.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430  -57.0000 -150.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega   33.00   61.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430  -99.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega   -7.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430    0.0000   60.0000 105
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0249584000
_diffrn_orient_matrix_UB_12      -0.0426169000
_diffrn_orient_matrix_UB_13      0.0141636000
_diffrn_orient_matrix_UB_21      -0.0015897000
_diffrn_orient_matrix_UB_22      0.0300356000
_diffrn_orient_matrix_UB_23      0.0423011000
_diffrn_orient_matrix_UB_31      -0.0293540000
_diffrn_orient_matrix_UB_32      0.0346278000
_diffrn_orient_matrix_UB_33      -0.0192630000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4600
_reflns_number_total             5999
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5999
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.046
_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)+(0.0361P)²+1.5721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1098
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O7) \\sim Ueq, Uanis(O7') \\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(O8')
\\sim Ueq, Uanis(O9) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms
of 0.02
3. Others
 Fixed Sof: O7(0.5) O8(0.65) O7'(0.5) O8'(0.35)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C18(H18), C20(H20), C21(H21), C23(H23), C25(H25), C26(H26), C27(H27), C28(H28)
4.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C)
4.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
Co1 Co 0.23983(2) 0.25584(3) 0.02505(2) 0.02338(11) Uani 1 1 d . . . . .
O1 O 0.20424(9) 0.27008(15) 0.14326(11) 0.0279(4) Uani 1 1 d . . . . .
O2 O 0.04051(12) 0.4792(2) 0.32031(14) 0.0517(6) Uani 1 1 d . . . . .
O3 O 0.32515(11) 0.10718(18) 0.14593(13) 0.0429(5) Uani 1 1 d . . . . .
H3 H 0.3366 0.0424 0.1266 0.064 Uiso 1 1 calc GR . . . .
O4 O 0.05925(11) 0.69248(17) -0.13957(13) 0.0421(5) Uani 1 1 d . . . . .
O5 O 0.15117(9) 0.32729(15) -0.01842(11) 0.0277(4) Uani 1 1 d . . . . .
O6 O 0.13927(11) 0.08449(18) 0.07148(14) 0.0404(5) Uani 1 1 d . . . . .
H6 H 0.1477(17) 0.143(3) 0.110(2) 0.055(10) Uiso 1 1 d . . . . .
N1 N 0.28730(11) 0.40448(18) 0.03817(13) 0.0267(5) Uani 1 1 d . . . . .
N2 N 0.33092(12) 0.19195(19) 0.07763(14) 0.0296(5) Uani 1 1 d . . . . .
N3 N 0.26348(11) 0.23480(18) -0.09813(14) 0.0262(5) Uani 1 1 d . . . . .
N4 N 0.19610(11) 0.10138(19) 0.01597(14) 0.0302(5) Uani 1 1 d . . . . .
C1 C 0.17760(14) 0.3719(2) 0.17011(16) 0.0275(6) Uani 1 1 d . . . . .
C2 C 0.12349(14) 0.3692(2) 0.23208(17) 0.0312(6) Uani 1 1 d . . . . .
H2 H 0.1074 0.2973 0.2534 0.037 Uiso 1 1 calc R . . . .
C3 C 0.09395(15) 0.4731(3) 0.26151(18) 0.0362(7) Uani 1 1 d . . . . .
C4 C 0.11812(17) 0.5825(3) 0.2317(2) 0.0450(8) Uani 1 1 d . . . . .
H4 H 0.0968 0.6520 0.2501 0.054 Uiso 1 1 calc R . . . .
C5 C 0.17346(17) 0.5856(3) 0.1751(2) 0.0410(7) Uani 1 1 d . . . . .
H5 H 0.1913 0.6585 0.1579 0.049 Uiso 1 1 calc R . . . .
C6 C 0.20434(14) 0.4825(2) 0.14196(17) 0.0303(6) Uani 1 1 d . . . . .
C7 C 0.26382(15) 0.4907(2) 0.08611(17) 0.0316(6) Uani 1 1 d . . . . .
H7 H 0.2876 0.5629 0.0838 0.038 Uiso 1 1 calc R . . . .
C8 C 0.35177(14) 0.4174(2) -0.00915(17) 0.0305(6) Uani 1 1 d . . . . .
C9 C 0.36078(17) 0.5114(3) -0.06689(19) 0.0417(7) Uani 1 1 d . . . . .
H9 H 0.3268 0.5721 -0.0718 0.050 Uiso 1 1 calc R . . . .
C10 C 0.42155(19) 0.5143(3) -0.1178(2) 0.0535(9) Uani 1 1 d . . . . .
H10 H 0.4276 0.5764 -0.1581 0.064 Uiso 1 1 calc R . . . .
C11 C 0.47242(18) 0.4261(3) -0.1087(2) 0.0579(9) Uani 1 1 d . . . . .
H11 H 0.5127 0.4286 -0.1431 0.069 Uiso 1 1 calc R . . . .
C12 C 0.46450(16) 0.3340(3) -0.0493(2) 0.0483(8) Uani 1 1 d . . . . .
H12 H 0.5002 0.2760 -0.0424 0.058 Uiso 1 1 calc R . . . .
C13 C 0.40325(15) 0.3269(3) 0.00057(18) 0.0352(7) Uani 1 1 d . . . . .
C14 C 0.39535(14) 0.2277(3) 0.06429(19) 0.0351(7) Uani 1 1 d . . . . .
C15 C 0.46163(16) 0.1733(3) 0.1129(3) 0.0616(10) Uani 1 1 d . . . . .
H15A H 0.4524 0.1566 0.1752 0.092 Uiso 1 1 calc GR . . . .
H15B H 0.5018 0.2271 0.1119 0.092 Uiso 1 1 calc GR . . . .
H15C H 0.4732 0.1013 0.0827 0.092 Uiso 1 1 calc GR . . . .
C16 C 0.01811(18) 0.3734(3) 0.3620(2) 0.0547(9) Uani 1 1 d . . . . .
H16A H -0.0008 0.3195 0.3155 0.082 Uiso 1 1 calc GR . . . .
H16B H -0.0190 0.3910 0.4025 0.082 Uiso 1 1 calc GR . . . .
H16C H 0.0590 0.3380 0.3963 0.082 Uiso 1 1 calc GR . . . .
C17 C 0.15229(13) 0.4121(2) -0.07940(16) 0.0256(6) Uani 1 1 d . . . . .
C18 C 0.10345(14) 0.5069(2) -0.07594(17) 0.0302(6) Uani 1 1 d . . . . .
H18 H 0.0712 0.5093 -0.0302 0.036 Uiso 1 1 calc R . . . .
C19 C 0.10300(15) 0.5962(2) -0.13985(18) 0.0315(6) Uani 1 1 d . . . . .
C20 C 0.15026(16) 0.5940(3) -0.21037(19) 0.0418(7) Uani 1 1 d . . . . .
H20 H 0.1497 0.6550 -0.2529 0.050 Uiso 1 1 calc R . . . .
C21 C 0.19685(15) 0.5020(2) -0.21607(18) 0.0363(7) Uani 1 1 d . . . . .
H21 H 0.2272 0.4996 -0.2639 0.044 Uiso 1 1 calc R . . . .
C22 C 0.20023(14) 0.4103(2) -0.15106(16) 0.0277(6) Uani 1 1 d . . . . .
C23 C 0.24559(14) 0.3118(2) -0.16140(17) 0.0295(6) Uani 1 1 d . . . . .
H23 H 0.2642 0.3013 -0.2181 0.035 Uiso 1 1 calc R . . . .
C24 C 0.29797(14) 0.1279(2) -0.12366(17) 0.0321(6) Uani 1 1 d . . . . .
C25 C 0.35517(16) 0.1321(3) -0.1800(2) 0.0436(7) Uani 1 1 d . . . . .
H25 H 0.3728 0.2044 -0.1985 0.052 Uiso 1 1 calc R . . . .
C26 C 0.38552(19) 0.0285(3) -0.2081(2) 0.0587(10) Uani 1 1 d . . . . .
H26 H 0.4240 0.0311 -0.2454 0.070 Uiso 1 1 calc R . . . .
C27 C 0.3594(2) -0.0783(3) -0.1815(2) 0.0614(10) Uani 1 1 d . . . . .
H27 H 0.3795 -0.1478 -0.2020 0.074 Uiso 1 1 calc R . . . .
C28 C 0.30367(18) -0.0829(3) -0.1246(2) 0.0503(8) Uani 1 1 d . . . . .
H28 H 0.2868 -0.1560 -0.1066 0.060 Uiso 1 1 calc R . . . .
C29 C 0.27164(15) 0.0197(2) -0.09309(19) 0.0362(7) Uani 1 1 d . . . . .
C30 C 0.21105(15) 0.0110(2) -0.03237(19) 0.0344(6) Uani 1 1 d . . . . .
C31 C 0.17002(19) -0.1019(3) -0.0249(2) 0.0542(9) Uani 1 1 d . . . . .
H31A H 0.1896 -0.1451 0.0278 0.081 Uiso 1 1 calc GR . . . .
H31B H 0.1744 -0.1484 -0.0790 0.081 Uiso 1 1 calc GR . . . .
H31C H 0.1197 -0.0848 -0.0186 0.081 Uiso 1 1 calc GR . . . .
C32 C 0.01350(17) 0.7071(3) -0.0660(2) 0.0444(7) Uani 1 1 d . . . . .
H32A H -0.0090 0.7834 -0.0703 0.067 Uiso 1 1 calc GR . . . .
H32B H 0.0421 0.7005 -0.0086 0.067 Uiso 1 1 calc GR . . . .
H32C H -0.0234 0.6471 -0.0697 0.067 Uiso 1 1 calc GR . . . .
O9 O 0.3682(2) -0.2723(3) 0.0945(3) 0.1392(17) Uani 1 1 d . U . . .
N5 N 0.3607(2) -0.1743(3) 0.1182(3) 0.0725(10) Uani 1 1 d . . . . .
O7 O 0.3008(5) -0.1725(7) 0.1538(7) 0.140(4) Uani 0.5 1 d . U P A 1
O8 O 0.3930(4) -0.0891(4) 0.0983(5) 0.1024(18) Uani 0.65 1 d . U P A 1
O7' O 0.3111(5) -0.1103(7) 0.1109(6) 0.114(3) Uani 0.5 1 d . U P A 2
O8' O 0.4202(6) -0.1414(12) 0.1690(9) 0.134(4) Uani 0.35 1 d . U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 1.9048(17) . ?
Co1 O5 1.8910(16) . ?
Co1 N1 1.901(2) . ?
Co1 N2 1.934(2) . ?
Co1 N3 1.903(2) . ?
Co1 N4 1.928(2) . ?
O1 C1 1.326(3) . ?
O2 C3 1.360(3) . ?
O2 C16 1.422(4) . ?
O3 H3 0.8200 . ?
O3 N2 1.397(3) . ?
O4 C19 1.357(3) . ?
O4 C32 1.428(3) . ?
O5 C17 1.313(3) . ?
O6 H6 0.87(3) . ?
O6 N4 1.389(3) . ?
N1 C7 1.297(3) . ?
N1 C8 1.430(3) . ?
N2 C14 1.285(3) . ?
N3 C23 1.297(3) . ?
N3 C24 1.431(3) . ?
N4 C30 1.287(3) . ?
C1 C2 1.400(3) . ?
C1 C6 1.420(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(4) . ?
C3 C4 1.399(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.364(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.403(4) . ?
C6 C7 1.421(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.378(4) . ?
C8 C13 1.398(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.394(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.371(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.395(4) . ?
C13 C14 1.475(4) . ?
C14 C15 1.499(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.405(3) . ?
C17 C22 1.424(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(3) . ?
C19 C20 1.402(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.357(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.408(3) . ?
C22 C23 1.410(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.389(4) . ?
C24 C29 1.405(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.377(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.370(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.374(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.398(4) . ?
C29 C30 1.485(4) . ?
C30 C31 1.495(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
O9 N5 1.175(4) . ?
N5 O7 1.259(8) . ?
N5 O8 1.183(5) . ?
N5 O7' 1.166(8) . ?
N5 O8' 1.330(10) . ?

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 N2 91.16(8) . . ?
O1 Co1 N4 88.14(8) . . ?
O5 Co1 O1 85.37(7) . . ?
O5 Co1 N1 91.97(8) . . ?
O5 Co1 N2 175.32(8) . . ?
O5 Co1 N3 89.46(8) . . ?
O5 Co1 N4 91.08(8) . . ?
N1 Co1 O1 91.25(8) . . ?
N1 Co1 N2 84.96(9) . . ?
N1 Co1 N3 93.96(9) . . ?
N1 Co1 N4 176.83(9) . . ?
N3 Co1 O1 172.79(8) . . ?
N3 Co1 N2 94.26(9) . . ?
N3 Co1 N4 86.92(9) . . ?
N4 Co1 N2 91.94(9) . . ?
C1 O1 Co1 120.33(15) . . ?
C3 O2 C16 118.5(2) . . ?
N2 O3 H3 109.5 . . ?
C19 O4 C32 118.8(2) . . ?
C17 O5 Co1 118.91(15) . . ?
N4 O6 H6 100(2) . . ?
C7 N1 Co1 123.46(18) . . ?
C7 N1 C8 120.7(2) . . ?
C8 N1 Co1 115.83(16) . . ?
O3 N2 Co1 115.49(16) . . ?
C14 N2 Co1 127.38(19) . . ?
C14 N2 O3 116.6(2) . . ?
C23 N3 Co1 121.89(18) . . ?
C23 N3 C24 118.5(2) . . ?
C24 N3 Co1 119.52(17) . . ?
O6 N4 Co1 114.57(16) . . ?
C30 N4 Co1 130.9(2) . . ?
C30 N4 O6 114.6(2) . . ?
O1 C1 C2 118.2(2) . . ?
O1 C1 C6 122.5(2) . . ?
C2 C1 C6 119.2(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C2 124.4(3) . . ?
O2 C3 C4 114.6(3) . . ?
C2 C3 C4 121.0(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.1(3) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C7 121.7(2) . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 C7 119.8(3) . . ?
N1 C7 C6 124.6(2) . . ?
N1 C7 H7 117.7 . . ?
C6 C7 H7 117.7 . . ?
C9 C8 N1 121.4(3) . . ?
C9 C8 C13 121.1(3) . . ?
C13 C8 N1 117.4(2) . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.1(3) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C14 121.6(2) . . ?
C12 C13 C8 118.5(3) . . ?
C12 C13 C14 119.9(3) . . ?
N2 C14 C13 118.3(2) . . ?
N2 C14 C15 121.9(3) . . ?
C13 C14 C15 119.8(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C17 C18 119.4(2) . . ?
O5 C17 C22 122.2(2) . . ?
C18 C17 C22 118.3(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.8 . . ?
O4 C19 C18 124.1(2) . . ?
O4 C19 C20 114.9(2) . . ?
C18 C19 C20 121.0(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.5(3) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.4(3) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 C17 119.3(2) . . ?
C21 C22 C23 120.5(2) . . ?
C23 C22 C17 119.9(2) . . ?
N3 C23 C22 125.2(2) . . ?
N3 C23 H23 117.4 . . ?
C22 C23 H23 117.4 . . ?
C25 C24 N3 120.0(3) . . ?
C25 C24 C29 121.1(3) . . ?
C29 C24 N3 118.9(2) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.6(3) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.5(3) . . ?
C27 C26 H26 119.7 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.1(3) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 119.2 . . ?
C27 C28 C29 121.6(3) . . ?
C29 C28 H28 119.2 . . ?
C24 C29 C30 123.0(2) . . ?
C28 C29 C24 117.1(3) . . ?
C28 C29 C30 119.9(3) . . ?
N4 C30 C29 118.7(2) . . ?
N4 C30 C31 120.6(3) . . ?
C29 C30 C31 120.7(3) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O4 C32 H32A 109.5 . . ?
O4 C32 H32B 109.5 . . ?
O4 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O9 N5 O7 105.4(5) . . ?
O9 N5 O8 128.7(5) . . ?
O9 N5 O8' 108.6(7) . . ?
O8 N5 O7 124.3(6) . . ?
O7' N5 O9 132.1(6) . . ?
O7' N5 O8' 118.9(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 O1 C1 C2 150.40(18) . . . . ?
Co1 O1 C1 C6 -32.8(3) . . . . ?
Co1 O5 C17 C18 -144.16(19) . . . . ?
Co1 O5 C17 C22 37.6(3) . . . . ?
Co1 N1 C7 C6 6.4(4) . . . . ?
Co1 N1 C8 C9 128.0(2) . . . . ?
Co1 N1 C8 C13 -47.9(3) . . . . ?
Co1 N2 C14 C13 -1.5(4) . . . . ?
Co1 N2 C14 C15 177.2(2) . . . . ?
Co1 N3 C23 C22 -8.1(4) . . . . ?
Co1 N3 C24 C25 -137.1(2) . . . . ?
Co1 N3 C24 C29 44.7(3) . . . . ?
Co1 N4 C30 C29 0.2(4) . . . . ?
Co1 N4 C30 C31 178.0(2) . . . . ?
O1 Co1 O5 C17 135.23(18) . . . . ?
O1 C1 C2 C3 -179.7(2) . . . . ?
O1 C1 C6 C5 -179.0(2) . . . . ?
O1 C1 C6 C7 -2.8(4) . . . . ?
O2 C3 C4 C5 177.7(3) . . . . ?
O3 N2 C14 C13 -173.0(2) . . . . ?
O3 N2 C14 C15 5.7(4) . . . . ?
O4 C19 C20 C21 179.3(3) . . . . ?
O5 C17 C18 C19 -179.2(2) . . . . ?
O5 C17 C22 C21 177.8(2) . . . . ?
O5 C17 C22 C23 3.7(4) . . . . ?
O6 N4 C30 C29 -179.2(2) . . . . ?
O6 N4 C30 C31 -1.5(4) . . . . ?
N1 Co1 O5 C17 44.14(18) . . . . ?
N1 C8 C9 C10 -174.2(2) . . . . ?
N1 C8 C13 C12 176.1(2) . . . . ?
N1 C8 C13 C14 -6.1(4) . . . . ?
N3 Co1 O5 C17 -49.81(18) . . . . ?
N3 C24 C25 C26 -176.6(3) . . . . ?
N3 C24 C29 C28 175.8(2) . . . . ?
N3 C24 C29 C30 -2.3(4) . . . . ?
N4 Co1 O5 C17 -136.72(18) . . . . ?
C1 C2 C3 O2 178.9(2) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C1 C6 C7 N1 17.5(4) . . . . ?
C2 C1 C6 C5 -2.2(4) . . . . ?
C2 C1 C6 C7 174.0(2) . . . . ?
C2 C3 C4 C5 -2.3(4) . . . . ?
C3 C4 C5 C6 3.4(5) . . . . ?
C4 C5 C6 C1 -1.2(4) . . . . ?
C4 C5 C6 C7 -177.5(3) . . . . ?
C5 C6 C7 N1 -166.3(3) . . . . ?
C6 C1 C2 C3 3.4(4) . . . . ?
C7 N1 C8 C9 -51.7(3) . . . . ?
C7 N1 C8 C13 132.5(3) . . . . ?
C8 N1 C7 C6 -174.0(2) . . . . ?
C8 C9 C10 C11 -1.5(5) . . . . ?
C8 C13 C14 N2 32.7(4) . . . . ?
C8 C13 C14 C15 -146.0(3) . . . . ?
C9 C8 C13 C12 0.3(4) . . . . ?
C9 C8 C13 C14 178.1(2) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C10 C11 C12 C13 2.0(5) . . . . ?
C11 C12 C13 C8 -2.0(4) . . . . ?
C11 C12 C13 C14 -179.9(3) . . . . ?
C12 C13 C14 N2 -149.5(3) . . . . ?
C12 C13 C14 C15 31.7(4) . . . . ?
C13 C8 C9 C10 1.5(4) . . . . ?
C16 O2 C3 C2 6.7(4) . . . . ?
C16 O2 C3 C4 -173.2(3) . . . . ?
C17 C18 C19 O4 -177.8(2) . . . . ?
C17 C18 C19 C20 1.0(4) . . . . ?
C17 C22 C23 N3 -20.0(4) . . . . ?
C18 C17 C22 C21 -0.5(4) . . . . ?
C18 C17 C22 C23 -174.6(2) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
C19 C20 C21 C22 -1.8(4) . . . . ?
C20 C21 C22 C17 1.9(4) . . . . ?
C20 C21 C22 C23 175.9(3) . . . . ?
C21 C22 C23 N3 166.0(3) . . . . ?
C22 C17 C18 C19 -0.9(4) . . . . ?
C23 N3 C24 C25 46.7(3) . . . . ?
C23 N3 C24 C29 -131.4(3) . . . . ?
C24 N3 C23 C22 168.0(2) . . . . ?
C24 C25 C26 C27 0.5(5) . . . . ?
C24 C29 C30 N4 -21.2(4) . . . . ?
C24 C29 C30 C31 161.0(3) . . . . ?
C25 C24 C29 C28 -2.3(4) . . . . ?
C25 C24 C29 C30 179.5(2) . . . . ?
C25 C26 C27 C28 -1.6(5) . . . . ?
C26 C27 C28 C29 0.7(5) . . . . ?
C27 C28 C29 C24 1.2(4) . . . . ?
C27 C28 C29 C30 179.4(3) . . . . ?
C28 C29 C30 N4 160.7(3) . . . . ?
C28 C29 C30 C31 -17.1(4) . . . . ?
C29 C24 C25 C26 1.5(4) . . . . ?
C32 O4 C19 C18 3.8(4) . . . . ?
C32 O4 C19 C20 -175.0(3) . . . . ?

_olex2_date_sample_data_collection 2018-05-15
_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_zhanghl_9
_database_code_depnum_ccdc_archive 'CCDC 1869622'
loop_
_audit_author_name
_audit_author_address
'lan qin Chai'
;Lanzhou Jiaotong University
China
;
_audit_update_record             
;
2018-09-25 deposited with the CCDC.	2019-07-04 downloaded from the CCDC.
;
_audit_creation_date             2017-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C32 H30 N4 Ni O6'
_chemical_formula_sum            'C32 H30 N4 Ni O6'
_chemical_formula_weight         625.31
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.4359(15)
_cell_length_b                   9.3017(3)
_cell_length_c                   17.2225(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 128.389(10)
_cell_angle_gamma                90.00
_cell_volume                     2817.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1745
_cell_measurement_temperature    291.74(10)
_cell_measurement_theta_max      26.9570
_cell_measurement_theta_min      3.5950
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5573
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.30
_diffrn_ambient_temperature      291.74(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -47.00   51.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -38.0000 -150.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega   -2.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000   60.0000 54
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0120477000
_diffrn_orient_matrix_UB_12      -0.0001776000
_diffrn_orient_matrix_UB_13      0.0295605000
_diffrn_orient_matrix_UB_21      -0.0383531000
_diffrn_orient_matrix_UB_22      -0.0068074000
_diffrn_orient_matrix_UB_23      -0.0432439000
_diffrn_orient_matrix_UB_31      0.0034652000
_diffrn_orient_matrix_UB_32      -0.0759401000
_diffrn_orient_matrix_UB_33      0.0037984000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2309
_reflns_number_total             2763
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2763
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0357P)²+3.0126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0986
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Ni1 Ni 0.5000 0.12585(4) 0.7500 0.02440(15) Uani 1 d . . 2 S T P
O1 O 0.56677(10) 0.28561(17) 0.84719(12) 0.0298(4) Uani 1 d . . 1 . . .
O2 O 0.74754(12) 0.4914(2) 1.16691(15) 0.0554(6) Uani 1 d . . 1 . . .
O3 O 0.53934(12) 0.2534(2) 0.62852(15) 0.0370(5) Uani 1 d . . 1 . . .
H3 H 0.5115(17) 0.296(3) 0.634(2) 0.039(9) Uiso 1 d . . 1 . . .
N1 N 0.58832(12) -0.0153(2) 0.83408(15) 0.0267(5) Uani 1 d . . 1 . . .
N2 N 0.54133(12) 0.1206(2) 0.66841(15) 0.0272(5) Uani 1 d . . 1 . . .
C1 C 0.62676(14) 0.2684(3) 0.94060(18) 0.0275(5) Uani 1 d . . 1 . . .
C2 C 0.65303(15) 0.3874(3) 1.00462(19) 0.0332(6) Uani 1 d . . 1 . . .
H2 H 0.6262 0.4734 0.9808 0.040 Uiso 1 calc . . 1 R . .
C3 C 0.71798(16) 0.3790(3) 1.1024(2) 0.0369(7) Uani 1 d . . 1 . . .
C4 C 0.75909(16) 0.2514(3) 1.1403(2) 0.0400(7) Uani 1 d . . 1 . . .
H4 H 0.8028 0.2459 1.2059 0.048 Uiso 1 calc . . 1 R . .
C5 C 0.73420(15) 0.1352(3) 1.0799(2) 0.0350(6) Uani 1 d . . 1 . . .
H5 H 0.7622 0.0506 1.1054 0.042 Uiso 1 calc . . 1 R . .
C6 C 0.66762(14) 0.1369(3) 0.98010(18) 0.0283(6) Uani 1 d . . 1 . . .
C7 C 0.64961(15) 0.0098(3) 0.92289(19) 0.0306(6) Uani 1 d . . 1 . . .
H7 H 0.6859 -0.0629 0.9527 0.037 Uiso 1 calc . . 1 R . .
C8 C 0.58662(14) -0.1404(3) 0.78457(19) 0.0295(6) Uani 1 d . . 1 . . .
C9 C 0.59323(16) -0.2764(3) 0.8221(2) 0.0395(7) Uani 1 d . . 1 . . .
H9 H 0.6001 -0.2861 0.8810 0.047 Uiso 1 calc . . 1 R . .
C10 C 0.58975(18) -0.3981(3) 0.7732(3) 0.0496(8) Uani 1 d . . 1 . . .
H10 H 0.5932 -0.4890 0.7982 0.059 Uiso 1 calc . . 1 R . .
C11 C 0.58115(19) -0.3835(3) 0.6871(3) 0.0526(9) Uani 1 d . . 1 . . .
H11 H 0.5790 -0.4649 0.6541 0.063 Uiso 1 calc . . 1 R . .
C12 C 0.57561(18) -0.2483(3) 0.6494(2) 0.0448(7) Uani 1 d . . 1 . . .
H12 H 0.5708 -0.2400 0.5920 0.054 Uiso 1 calc . . 1 R . .
C13 C 0.57713(15) -0.1241(3) 0.6962(2) 0.0309(6) Uani 1 d . . 1 . . .
C14 C 0.57171(14) 0.0188(3) 0.65386(18) 0.0283(6) Uani 1 d . . 1 . . .
C15 C 0.60173(17) 0.0390(3) 0.5976(2) 0.0409(7) Uani 1 d . . 1 . . .
H15A H 0.5896 0.1341 0.5700 0.061 Uiso 1 calc . . 1 GR . .
H15B H 0.5789 -0.0305 0.5452 0.061 Uiso 1 calc . . 1 GR . .
H15C H 0.6559 0.0265 0.6415 0.061 Uiso 1 calc . . 1 GR . .
C16 C 0.7125(2) 0.6279(3) 1.1321(3) 0.0640(10) Uani 1 d . . 1 . . .
H16A H 0.7127 0.6579 1.0789 0.096 Uiso 1 calc . . 1 GR . .
H16B H 0.7400 0.6965 1.1851 0.096 Uiso 1 calc . . 1 GR . .
H16C H 0.6610 0.6219 1.1087 0.096 Uiso 1 calc . . 1 GR . .


_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 2.0347(17) . ?
Ni1 O1 2.0347(17) 2_656 ?
Ni1 N1 2.045(2) 2_656 ?
Ni1 N1 2.045(2) . ?
Ni1 N2 2.111(2) 2_656 ?
Ni1 N2 2.111(2) . ?
O1 C1 1.318(3) . ?
O2 C3 1.361(3) . ?
O2 C16 1.416(4) . ?
O3 H3 0.80(3) . ?
O3 N2 1.401(2) . ?
N1 C7 1.293(3) . ?
N1 C8 1.429(3) . ?
N2 C14 1.279(3) . ?
C1 C2 1.408(3) . ?
C1 C6 1.422(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(4) . ?
C3 C4 1.392(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.357(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.414(4) . ?
C6 C7 1.428(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.386(3) . ?
C8 C13 1.408(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.397(3) . ?
C13 C14 1.485(3) . ?
C14 C15 1.497(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 86.17(9) . 2_656 ?
O1 Ni1 N1 161.07(7) . 2_656 ?
O1 Ni1 N1 89.53(8) 2_656 2_656 ?
O1 Ni1 N1 89.53(8) . . ?
O1 Ni1 N1 161.07(7) 2_656 . ?
O1 Ni1 N2 99.27(7) 2_656 2_656 ?
O1 Ni1 N2 99.27(7) . . ?
O1 Ni1 N2 82.68(7) 2_656 . ?
O1 Ni1 N2 82.68(7) . 2_656 ?
N1 Ni1 N1 100.13(11) 2_656 . ?
N1 Ni1 N2 79.83(8) 2_656 2_656 ?
N1 Ni1 N2 79.83(8) . . ?
N1 Ni1 N2 98.44(8) 2_656 . ?
N1 Ni1 N2 98.44(8) . 2_656 ?
N2 Ni1 N2 177.35(10) 2_656 . ?
C1 O1 Ni1 125.98(15) . . ?
C3 O2 C16 118.8(2) . . ?
N2 O3 H3 99(2) . . ?
C7 N1 Ni1 124.92(17) . . ?
C7 N1 C8 117.9(2) . . ?
C8 N1 Ni1 116.43(16) . . ?
O3 N2 Ni1 114.37(14) . . ?
C14 N2 Ni1 130.96(17) . . ?
C14 N2 O3 114.5(2) . . ?
O1 C1 C2 118.3(2) . . ?
O1 C1 C6 123.7(2) . . ?
C2 C1 C6 118.0(2) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
O2 C3 C2 124.1(3) . . ?
O2 C3 C4 115.3(3) . . ?
C2 C3 C4 120.6(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 118.5 . . ?
C4 C5 C6 123.0(3) . . ?
C6 C5 H5 118.5 . . ?
C1 C6 C7 124.0(2) . . ?
C5 C6 C1 118.2(2) . . ?
C5 C6 C7 117.5(2) . . ?
N1 C7 C6 127.1(2) . . ?
N1 C7 H7 116.4 . . ?
C6 C7 H7 116.4 . . ?
C9 C8 N1 120.6(2) . . ?
C9 C8 C13 120.2(2) . . ?
C13 C8 N1 119.2(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.2(3) . . ?
C13 C12 H12 119.4 . . ?
C8 C13 C14 122.6(2) . . ?
C12 C13 C8 117.9(2) . . ?
C12 C13 C14 119.5(2) . . ?
N2 C14 C13 117.2(2) . . ?
N2 C14 C15 122.9(2) . . ?
C13 C14 C15 119.9(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 C2 -161.70(16) . . . . ?
Ni1 O1 C1 C6 19.7(3) . . . . ?
Ni1 N1 C7 C6 1.1(4) . . . . ?
Ni1 N1 C8 C9 -127.1(2) . . . . ?
Ni1 N1 C8 C13 52.0(3) . . . . ?
Ni1 N2 C14 C13 3.1(4) . . . . ?
Ni1 N2 C14 C15 -176.40(19) . . . . ?
O1 Ni1 O1 C1 175.2(2) 2_656 . . . ?
O1 Ni1 N1 C7 89.7(3) 2_656 . . . ?
O1 Ni1 N1 C7 13.0(2) . . . . ?
O1 Ni1 N1 C8 -80.0(3) 2_656 . . . ?
O1 Ni1 N1 C8 -156.70(16) . . . . ?
O1 Ni1 N2 O3 -54.32(16) . . . . ?
O1 Ni1 N2 O3 30.56(15) 2_656 . . . ?
O1 Ni1 N2 C14 121.2(2) . . . . ?
O1 Ni1 N2 C14 -153.9(2) 2_656 . . . ?
O1 C1 C2 C3 -176.7(2) . . . . ?
O1 C1 C6 C5 175.6(2) . . . . ?
O1 C1 C6 C7 1.6(4) . . . . ?
O2 C3 C4 C5 -178.6(2) . . . . ?
O3 N2 C14 C13 178.7(2) . . . . ?
O3 N2 C14 C15 -0.8(4) . . . . ?
N1 Ni1 O1 C1 98.0(3) 2_656 . . . ?
N1 Ni1 O1 C1 -23.21(19) . . . . ?
N1 Ni1 N1 C7 -150.7(2) 2_656 . . . ?
N1 Ni1 N1 C8 39.67(14) 2_656 . . . ?
N1 Ni1 N2 O3 -142.16(17) . . . . ?
N1 Ni1 N2 O3 118.98(16) 2_656 . . . ?
N1 Ni1 N2 C14 33.4(2) . . . . ?
N1 Ni1 N2 C14 -65.5(2) 2_656 . . . ?
N1 C8 C9 C10 178.4(3) . . . . ?
N1 C8 C13 C12 -179.9(2) . . . . ?
N1 C8 C13 C14 2.4(4) . . . . ?
N2 Ni1 O1 C1 -102.83(19) . . . . ?
N2 Ni1 O1 C1 75.36(19) 2_656 . . . ?
N2 Ni1 N1 C7 112.5(2) . . . . ?
N2 Ni1 N1 C7 -69.6(2) 2_656 . . . ?
N2 Ni1 N1 C8 120.77(16) 2_656 . . . ?
N2 Ni1 N1 C8 -57.19(16) . . . . ?
N2 Ni1 N2 O3 168.24(15) 2_656 . . . ?
N2 Ni1 N2 C14 -16.2(2) 2_656 . . . ?
C1 C2 C3 O2 177.8(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C1 C6 C7 N1 -12.9(4) . . . . ?
C2 C1 C6 C5 -3.0(3) . . . . ?
C2 C1 C6 C7 -177.0(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C4 C5 C6 C1 2.5(4) . . . . ?
C4 C5 C6 C7 176.9(2) . . . . ?
C5 C6 C7 N1 173.0(2) . . . . ?
C6 C1 C2 C3 2.0(4) . . . . ?
C7 N1 C8 C9 62.4(3) . . . . ?
C7 N1 C8 C13 -118.4(3) . . . . ?
C8 N1 C7 C6 170.6(2) . . . . ?
C8 C9 C10 C11 1.3(5) . . . . ?
C8 C13 C14 N2 -31.7(4) . . . . ?
C8 C13 C14 C15 147.9(3) . . . . ?
C9 C8 C13 C12 -0.8(4) . . . . ?
C9 C8 C13 C14 -178.4(2) . . . . ?
C9 C10 C11 C12 -0.3(5) . . . . ?
C10 C11 C12 C13 -1.2(5) . . . . ?
C11 C12 C13 C8 1.8(4) . . . . ?
C11 C12 C13 C14 179.5(3) . . . . ?
C12 C13 C14 N2 150.7(3) . . . . ?
C12 C13 C14 C15 -29.7(4) . . . . ?
C13 C8 C9 C10 -0.8(4) . . . . ?
C16 O2 C3 C2 -3.0(4) . . . . ?
C16 O2 C3 C4 175.3(3) . . . . ?

_olex2_date_sample_data_collection 2017-03-10
_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_zhanghl_5
_database_code_depnum_ccdc_archive 'CCDC 1869623'
loop_
_audit_author_name
_audit_author_address
'lan qin Chai'
;Lanzhou Jiaotong University
China
;
_audit_update_record             
;
2018-09-25 deposited with the CCDC.	2019-07-04 downloaded from the CCDC.
;
_audit_creation_date             2017-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 Cu N3 O6, C H4 O'
_chemical_formula_sum            'C17 H19 Cu N3 O7'
_chemical_formula_weight         440.89
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cu'
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9369(17)
_cell_length_b                   9.3422(14)
_cell_length_c                   13.803(4)
_cell_angle_alpha                96.523(18)
_cell_angle_beta                 105.99(2)
_cell_angle_gamma                105.591(16)
_cell_volume                     928.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1035
_cell_measurement_temperature    294.28(15)
_cell_measurement_theta_max      23.9730
_cell_measurement_theta_min      3.6150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             454
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0957
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5904
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.479
_diffrn_ambient_temperature      294.28(15)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -4.00   28.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.1983  -99.0000 -150.0000 16

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00  102.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8545   19.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
  3 omega   36.00  116.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8545  178.0000  150.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega   65.00  111.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8545  178.0000  -90.0000 23

#__ type_ start__ end____ width___ exp.time_
  5 omega   -5.00   77.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8545   57.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
  6 omega   29.00   95.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8545   38.0000  -90.0000 33
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0652073000
_diffrn_orient_matrix_UB_12      0.0139005000
_diffrn_orient_matrix_UB_13      0.0230277000
_diffrn_orient_matrix_UB_21      0.0702091000
_diffrn_orient_matrix_UB_22      0.0267398000
_diffrn_orient_matrix_UB_23      0.0485251000
_diffrn_orient_matrix_UB_31      0.0201657000
_diffrn_orient_matrix_UB_32      0.0746384000
_diffrn_orient_matrix_UB_33      -0.0097469000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2519
_reflns_number_total             3638
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3638
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.054
_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)+(0.0242P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.1078
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C14(H14)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_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
Cu1 Cu 0.73969(7) 0.88870(5) 0.67033(4) 0.03323(18) Uani 1 1 d . . . . .
O1 O 0.5320(5) 0.9862(4) 0.7924(2) 0.0519(9) Uani 1 1 d . . . . .
H1 H 0.483436 0.992219 0.733013 0.078 Uiso 1 1 calc GR . . . .
O2 O 0.6951(4) 0.8307(3) 0.5279(2) 0.0344(7) Uani 1 1 d . . . . .
O3 O 0.5669(4) 0.4902(3) 0.2133(2) 0.0481(9) Uani 1 1 d . . . . .
O4 O 0.7495(4) 1.1004(3) 0.6528(2) 0.0471(9) Uani 1 1 d . . . . .
O5 O 1.0185(4) 1.1136(3) 0.7532(3) 0.0544(9) Uani 1 1 d . . . . .
O6 O 0.9613(5) 1.3188(3) 0.7180(3) 0.0857(14) Uani 1 1 d . . . . .
N1 N 0.6646(5) 0.9127(3) 0.7949(3) 0.0344(9) Uani 1 1 d . . . . .
N2 N 0.8180(4) 0.7209(3) 0.7084(3) 0.0288(8) Uani 1 1 d . . . . .
N3 N 0.9148(6) 1.1802(4) 0.7091(3) 0.0465(10) Uani 1 1 d . . . . .
C1 C 0.6214(7) 0.8793(5) 0.9579(4) 0.0577(14) Uani 1 1 d . . . . .
H1A H 0.684498 0.976983 1.002725 0.087 Uiso 1 1 calc GR . . . .
H1B H 0.627809 0.801271 0.997051 0.087 Uiso 1 1 calc GR . . . .
H1C H 0.494495 0.871152 0.925773 0.087 Uiso 1 1 calc GR . . . .
C2 C 0.7103(6) 0.8617(4) 0.8773(3) 0.0332(10) Uani 1 1 d . . . . .
C3 C 0.8586(6) 0.7905(4) 0.8935(3) 0.0315(10) Uani 1 1 d . . . . .
C4 C 0.9495(7) 0.7843(5) 0.9940(3) 0.0436(12) Uani 1 1 d . . . . .
H4 H 0.916642 0.827210 1.047348 0.052 Uiso 1 1 calc R . . . .
C5 C 1.0864(7) 0.7170(5) 1.0175(4) 0.0555(14) Uani 1 1 d . . . . .
H5 H 1.142886 0.712724 1.085328 0.067 Uiso 1 1 calc R . . . .
C6 C 1.1383(7) 0.6563(5) 0.9391(4) 0.0503(13) Uani 1 1 d . . . . .
H6 H 1.232020 0.612231 0.954069 0.060 Uiso 1 1 calc R . . . .
C7 C 1.0520(6) 0.6604(4) 0.8383(3) 0.0381(11) Uani 1 1 d . . . . .
H7 H 1.090474 0.621187 0.786300 0.046 Uiso 1 1 calc R . . . .
C8 C 0.9083(5) 0.7224(4) 0.8134(3) 0.0284(10) Uani 1 1 d . . . . .
C9 C 0.7947(5) 0.6012(4) 0.6396(3) 0.0309(10) Uani 1 1 d . . . . .
H9 H 0.822297 0.519249 0.664956 0.037 Uiso 1 1 calc R . . . .
C10 C 0.7330(5) 0.5842(4) 0.5328(3) 0.0288(10) Uani 1 1 d . . . . .
C11 C 0.7192(6) 0.4438(4) 0.4723(3) 0.0351(11) Uani 1 1 d . . . . .
H11 H 0.747723 0.368223 0.505777 0.042 Uiso 1 1 calc R . . . .
C12 C 0.6665(6) 0.4173(4) 0.3689(4) 0.0370(11) Uani 1 1 d . . . . .
H12 H 0.659890 0.325256 0.331896 0.044 Uiso 1 1 calc R . . . .
C13 C 0.6217(6) 0.5296(4) 0.3173(3) 0.0344(10) Uani 1 1 d . . . . .
C14 C 0.6315(6) 0.6669(4) 0.3722(3) 0.0349(11) Uani 1 1 d . . . . .
H14 H 0.600581 0.739914 0.336742 0.042 Uiso 1 1 calc R . . . .
C15 C 0.6872(5) 0.6981(4) 0.4800(3) 0.0279(10) Uani 1 1 d . . . . .
C16 C 0.5191(8) 0.5986(5) 0.1562(4) 0.0747(18) Uani 1 1 d . . . . .
H16A H 0.478374 0.555754 0.083994 0.112 Uiso 1 1 calc GR . . . .
H16B H 0.624903 0.687176 0.172314 0.112 Uiso 1 1 calc GR . . . .
H16C H 0.421535 0.626232 0.173850 0.112 Uiso 1 1 calc GR . . . .
O7 O 0.3515(4) 0.9563(3) 0.5977(3) 0.0418(8) Uani 1 1 d . . . . .
H7A H 0.367(7) 1.013(5) 0.558(4) 0.059(17) Uiso 1 1 d . . . . .
C17 C 0.1607(6) 0.9023(5) 0.5850(4) 0.0541(14) Uani 1 1 d . . . . .
H17A H 0.094915 0.844775 0.516239 0.081 Uiso 1 1 calc GR . . . .
H17B H 0.116579 0.986694 0.596663 0.081 Uiso 1 1 calc GR . . . .
H17C H 0.141143 0.838643 0.633375 0.081 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.886(3) . ?
Cu1 O4 2.003(3) . ?
Cu1 N1 1.977(4) . ?
Cu1 N2 1.911(3) . ?
O1 H1 0.8200 . ?
O1 N1 1.397(4) . ?
O2 C15 1.313(4) . ?
O3 C13 1.355(5) . ?
O3 C16 1.419(5) . ?
O4 N3 1.290(5) . ?
O5 N3 1.233(4) . ?
O6 N3 1.228(4) . ?
N1 C2 1.282(5) . ?
N2 C8 1.426(5) . ?
N2 C9 1.318(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.488(6) . ?
C2 C3 1.479(5) . ?
C3 C4 1.392(6) . ?
C3 C8 1.414(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.392(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.394(5) . ?
C10 C11 1.433(5) . ?
C10 C15 1.426(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.345(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.401(5) . ?
C13 C14 1.384(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.402(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O7 H7A 0.82(4) . ?
O7 C17 1.415(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
O2 Cu1 O4 89.68(12) . . ?
O2 Cu1 N1 154.14(14) . . ?
O2 Cu1 N2 96.25(12) . . ?
N1 Cu1 O4 92.33(13) . . ?
N2 Cu1 O4 160.50(14) . . ?
N2 Cu1 N1 90.36(14) . . ?
N1 O1 H1 109.5 . . ?
C15 O2 Cu1 125.8(2) . . ?
C13 O3 C16 117.6(3) . . ?
N3 O4 Cu1 103.3(2) . . ?
O1 N1 Cu1 117.0(2) . . ?
C2 N1 Cu1 129.6(3) . . ?
C2 N1 O1 113.2(4) . . ?
C8 N2 Cu1 120.7(2) . . ?
C9 N2 Cu1 122.0(3) . . ?
C9 N2 C8 117.3(3) . . ?
O5 N3 O4 118.2(3) . . ?
O6 N3 O4 118.9(4) . . ?
O6 N3 O5 122.9(4) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 120.7(4) . . ?
N1 C2 C3 119.1(4) . . ?
C3 C2 C1 120.2(4) . . ?
C4 C3 C2 117.7(4) . . ?
C4 C3 C8 117.9(4) . . ?
C8 C3 C2 124.3(4) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 C3 122.5(4) . . ?
C5 C4 H4 118.8 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 118.9(5) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.4(4) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.1(4) . . ?
C8 C7 H7 119.5 . . ?
C3 C8 N2 121.1(4) . . ?
C7 C8 N2 119.8(4) . . ?
C7 C8 C3 119.1(4) . . ?
N2 C9 H9 116.5 . . ?
N2 C9 C10 126.9(4) . . ?
C10 C9 H9 116.5 . . ?
C9 C10 C11 117.5(4) . . ?
C9 C10 C15 124.5(4) . . ?
C15 C10 C11 118.0(4) . . ?
C10 C11 H11 118.8 . . ?
C12 C11 C10 122.3(4) . . ?
C12 C11 H11 118.8 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.5(4) . . ?
C13 C12 H12 120.2 . . ?
O3 C13 C12 114.7(4) . . ?
O3 C13 C14 124.9(4) . . ?
C14 C13 C12 120.4(4) . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.4(4) . . ?
C15 C14 H14 119.3 . . ?
O2 C15 C10 123.0(4) . . ?
O2 C15 C14 118.6(4) . . ?
C14 C15 C10 118.4(4) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 O7 H7A 109(3) . . ?
O7 C17 H17A 109.5 . . ?
O7 C17 H17B 109.5 . . ?
O7 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
Cu1 O2 C15 C10 -7.5(5) . . . . ?
Cu1 O2 C15 C14 172.7(3) . . . . ?
Cu1 O4 N3 O5 2.0(4) . . . . ?
Cu1 O4 N3 O6 -176.8(3) . . . . ?
Cu1 N1 C2 C1 -173.4(3) . . . . ?
Cu1 N1 C2 C3 9.2(6) . . . . ?
Cu1 N2 C8 C3 35.5(5) . . . . ?
Cu1 N2 C8 C7 -142.3(3) . . . . ?
Cu1 N2 C9 C10 7.8(6) . . . . ?
O1 N1 C2 C1 1.6(6) . . . . ?
O1 N1 C2 C3 -175.9(3) . . . . ?
O3 C13 C14 C15 179.1(4) . . . . ?
O4 Cu1 O2 C15 173.8(3) . . . . ?
N1 Cu1 O2 C15 -91.5(4) . . . . ?
N1 C2 C3 C4 158.1(4) . . . . ?
N1 C2 C3 C8 -24.9(6) . . . . ?
N2 Cu1 O2 C15 12.5(3) . . . . ?
N2 C9 C10 C11 179.5(4) . . . . ?
N2 C9 C10 C15 1.1(7) . . . . ?
C1 C2 C3 C4 -19.4(6) . . . . ?
C1 C2 C3 C8 157.6(4) . . . . ?
C2 C3 C4 C5 178.3(4) . . . . ?
C2 C3 C8 N2 1.4(6) . . . . ?
C2 C3 C8 C7 179.2(4) . . . . ?
C3 C4 C5 C6 1.4(7) . . . . ?
C4 C3 C8 N2 178.5(3) . . . . ?
C4 C3 C8 C7 -3.7(6) . . . . ?
C4 C5 C6 C7 -1.2(8) . . . . ?
C5 C6 C7 C8 -1.6(7) . . . . ?
C6 C7 C8 N2 -178.1(4) . . . . ?
C6 C7 C8 C3 4.0(6) . . . . ?
C8 N2 C9 C10 -170.9(4) . . . . ?
C8 C3 C4 C5 1.1(6) . . . . ?
C9 N2 C8 C3 -145.7(4) . . . . ?
C9 N2 C8 C7 36.4(5) . . . . ?
C9 C10 C11 C12 -178.0(4) . . . . ?
C9 C10 C15 O2 -1.5(6) . . . . ?
C9 C10 C15 C14 178.3(4) . . . . ?
C10 C11 C12 C13 -0.5(7) . . . . ?
C11 C10 C15 O2 -180.0(3) . . . . ?
C11 C10 C15 C14 -0.1(6) . . . . ?
C11 C12 C13 O3 -178.8(4) . . . . ?
C11 C12 C13 C14 0.1(6) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
C13 C14 C15 O2 179.5(4) . . . . ?
C13 C14 C15 C10 -0.3(6) . . . . ?
C15 C10 C11 C12 0.5(6) . . . . ?
C16 O3 C13 C12 179.9(4) . . . . ?
C16 O3 C13 C14 1.1(7) . . . . ?

_olex2_date_sample_data_collection 2017-04-07
_olex2_submission_special_instructions 'No special instructions were received'
