# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_wangzhengxin-ni-20190117
_database_code_depnum_ccdc_archive 'CCDC 1969897'
loop_
_audit_author_name
_audit_author_address
'Yajie Zhang'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2019-12-04 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2019-01-17
_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         'C20 H22 N8 Ni O6'
_chemical_formula_sum            'C20 H22 N8 Ni O6'
_chemical_formula_weight         529.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ni C H O N Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   9.0895(2)
_cell_length_b                   15.5758(3)
_cell_length_c                   7.7921(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.169(2)
_cell_angle_gamma                90
_cell_volume                     1078.39(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3177
_cell_measurement_temperature    293
_cell_measurement_theta_max      76.1660
_cell_measurement_theta_min      2.8330
_shelx_estimated_absorpt_T_max   0.713
_shelx_estimated_absorpt_T_min   0.713
_exptl_absorpt_coefficient_mu    1.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5599
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.065
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_min         4.977
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  67.00   0.50    0.05    --   43.80 -57.00  30.00  192
  2  ω     53.00  78.00   0.50    0.05    --   43.80-134.00 167.00   50
  3  ω     38.00 114.00   0.50    0.10    --  111.75-134.00 167.00  152
  4  ω     83.00 125.00   0.50    0.10    --  111.75-134.00 -12.00   84
  5  ω     53.00  79.00   0.50    0.10    --  111.75 -94.00-150.00   52
  6  ω     39.00 108.00   0.50    0.10    --  111.75 -94.00-180.00  138
  7  ω     39.00 134.00   0.50    0.10    --  111.75 -45.00 -60.00  190
  8  ω     88.00 114.00   0.50    0.10    --  111.75  30.00  60.00   52
  9  ω    136.00 178.00   0.50    0.10    --  111.75  30.00  60.00   84
 10  ω    140.00 165.00   0.50    0.10    --  111.75  45.00 150.00   50
 11  ω    111.00 137.00   0.50    0.10    --  111.75 134.00  54.00   52
 12  ω     91.00 136.00   0.50    0.10    --  111.75  45.00 150.00   90
 13  ω     41.00  72.00   0.50    0.10    --  111.75 -94.00 -30.00   62
 14  ω    -52.00 -21.00   0.50    0.05    --  -43.80 -57.00-120.00   62
 15  ω   -104.00 -65.00   0.50    0.10    --  -90.25-134.00 -12.00   78
 16  ω   -118.00 -92.00   0.50    0.05    --  -43.80-134.00 -12.00   52
 17  ω    -88.00 -54.00   0.50    0.05    --  -43.80 134.00-125.00   68
 18  ω    -82.00 -57.00   0.50    0.10    --  -90.25 134.00-125.00   50
 19  ω   -113.00 -71.00   0.50    0.05    --  -43.80 -57.00-120.00   84
 20  ω   -155.00 -96.00   0.50    0.10    --  -90.25 -94.00  90.00  118
 21  ω   -114.00 -77.00   0.50    0.05    --  -43.80-134.00 167.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0613710000
_diffrn_orient_matrix_UB_12      -0.0922266000
_diffrn_orient_matrix_UB_13      0.0007490000
_diffrn_orient_matrix_UB_21      -0.1584344000
_diffrn_orient_matrix_UB_22      -0.0357274000
_diffrn_orient_matrix_UB_23      -0.0024562000
_diffrn_orient_matrix_UB_31      -0.0343580000
_diffrn_orient_matrix_UB_32      0.0001640000
_diffrn_orient_matrix_UB_33      -0.2022808000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1753
_reflns_number_total             1924
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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         0.234
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1924
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.074
_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)+(0.0405P)²+0.7782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0929
_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. Restrained distances
 O3-H3B
 0.85 with sigma of 0.01
3.a Rotating group:
 O3(H3A)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_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 0.500000 0.500000 0.02095(16) Uani 1 2 d S T P . .
O1 O 0.2502(2) 0.62916(11) 0.1327(2) 0.0399(4) Uani 1 1 d . . . . .
O2 O 0.14096(16) 0.54130(9) 0.35705(18) 0.0256(3) Uani 1 1 d . . . . .
O3 O 0.00359(19) 0.62323(10) 0.6224(2) 0.0317(4) Uani 1 1 d D . . . .
H3A H -0.040352 0.620380 0.709953 0.048 Uiso 1 1 d GR . . . .
N1 N 0.18420(19) 0.46986(11) 0.6934(2) 0.0226(4) Uani 1 1 d . . . . .
N2 N 0.1677(2) 0.41559(11) 0.8338(2) 0.0238(4) Uani 1 1 d . . . . .
N3 N 0.1130(3) 0.30059(12) 0.9668(2) 0.0370(5) Uani 1 1 d . . . . .
N4 N 0.1205(2) 0.36985(13) 1.0800(2) 0.0352(5) Uani 1 1 d . . . . .
C1 C 0.3398(3) 0.62340(13) 0.2976(3) 0.0268(4) Uani 1 1 d . . . . .
C2 C 0.4790(3) 0.66025(14) 0.3500(3) 0.0312(5) Uani 1 1 d . . . . .
H2 H 0.518961 0.693024 0.271085 0.037 Uiso 1 1 calc R . . . .
C3 C 0.5616(2) 0.64874(15) 0.5223(3) 0.0349(5) Uani 1 1 d . . . . .
H3 H 0.655671 0.674163 0.557617 0.042 Uiso 1 1 calc R . . . .
C4 C 0.5037(2) 0.60050(15) 0.6368(3) 0.0314(5) Uani 1 1 d . . . . .
H4 H 0.560001 0.592386 0.749947 0.038 Uiso 1 1 calc R . . . .
C5 C 0.3598(2) 0.56212(13) 0.5886(3) 0.0247(4) Uani 1 1 d . . . . .
C6 C 0.2726(2) 0.57329(12) 0.4151(3) 0.0220(4) Uani 1 1 d . . . . .
C7 C 0.2913(4) 0.69008(18) 0.0155(3) 0.0511(7) Uani 1 1 d . . . . .
H7A H 0.215348 0.691660 -0.090819 0.077 Uiso 1 1 calc GR . . . .
H7B H 0.385866 0.673943 -0.011264 0.077 Uiso 1 1 calc GR . . . .
H7C H 0.300301 0.745822 0.069251 0.077 Uiso 1 1 calc GR . . . .
C8 C 0.3134(2) 0.50755(13) 0.7145(3) 0.0237(4) Uani 1 1 d . . . . .
H8 H 0.381603 0.498383 0.819940 0.028 Uiso 1 1 calc R . . . .
C9 C 0.1398(3) 0.33066(14) 0.8203(3) 0.0345(5) Uani 1 1 d . . . . .
H9 H 0.139775 0.298010 0.720315 0.041 Uiso 1 1 calc R . . . .
C10 C 0.1519(3) 0.43770(14) 0.9970(3) 0.0304(5) Uani 1 1 d . . . . .
H10 H 0.161977 0.493019 1.042904 0.037 Uiso 1 1 calc R . . . .
H3B H -0.013(4) 0.6728(11) 0.577(4) 0.062(10) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O2 1.9743(14) . ?
Ni1 O2 1.9743(14) 3_566 ?
Ni1 O3 2.1404(15) 3_566 ?
Ni1 O3 2.1404(15) . ?
Ni1 N1 2.0571(16) 3_566 ?
Ni1 N1 2.0571(16) . ?
O1 C1 1.372(3) . ?
O1 C7 1.421(3) . ?
O2 C6 1.287(2) . ?
N1 N2 1.415(2) . ?
N1 C8 1.292(3) . ?
N2 C9 1.347(3) . ?
N2 C10 1.354(3) . ?
N3 N4 1.386(3) . ?
N3 C9 1.304(3) . ?
N4 C10 1.302(3) . ?
C1 C2 1.371(3) . ?
C1 C6 1.434(3) . ?
C2 C3 1.404(4) . ?
C3 C4 1.355(3) . ?
C4 C5 1.415(3) . ?
C5 C6 1.426(3) . ?
C5 C8 1.427(3) . ?

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 Ni1 O2 180.00(5) . 3_566 ?
O2 Ni1 O3 90.48(6) . . ?
O2 Ni1 O3 89.52(6) 3_566 . ?
O2 Ni1 O3 89.52(6) . 3_566 ?
O2 Ni1 O3 90.48(6) 3_566 3_566 ?
O2 Ni1 N1 92.12(6) . 3_566 ?
O2 Ni1 N1 87.88(6) . . ?
O2 Ni1 N1 92.12(6) 3_566 . ?
O2 Ni1 N1 87.88(6) 3_566 3_566 ?
O3 Ni1 O3 180.0 3_566 . ?
N1 Ni1 O3 86.83(7) . . ?
N1 Ni1 O3 93.17(7) . 3_566 ?
N1 Ni1 O3 93.18(7) 3_566 . ?
N1 Ni1 O3 86.82(7) 3_566 3_566 ?
N1 Ni1 N1 180.0 3_566 . ?
C1 O1 C7 117.49(19) . . ?
C6 O2 Ni1 126.41(12) . . ?
N2 N1 Ni1 120.02(12) . . ?
C8 N1 Ni1 124.53(14) . . ?
C8 N1 N2 114.50(16) . . ?
C9 N2 N1 125.10(17) . . ?
C9 N2 C10 105.53(18) . . ?
C10 N2 N1 128.57(18) . . ?
C9 N3 N4 106.53(18) . . ?
C10 N4 N3 107.58(17) . . ?
O1 C1 C6 112.67(18) . . ?
C2 C1 O1 125.45(19) . . ?
C2 C1 C6 121.9(2) . . ?
C1 C2 C3 120.3(2) . . ?
C4 C3 C2 119.8(2) . . ?
C3 C4 C5 121.7(2) . . ?
C4 C5 C6 119.87(19) . . ?
C4 C5 C8 117.34(19) . . ?
C6 C5 C8 122.60(18) . . ?
O2 C6 C1 118.40(18) . . ?
O2 C6 C5 125.14(18) . . ?
C5 C6 C1 116.45(18) . . ?
N1 C8 C5 125.13(19) . . ?
N3 C9 N2 110.55(19) . . ?
N4 C10 N2 109.77(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.159
_oxdiff_exptl_absorpt_empirical_full_min 0.902
_exptl_crystal_preparation       'Magnetic properties'
