# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_1_sq
_database_code_depnum_ccdc_archive 'CCDC 2141771'
loop_
_audit_author_name
_audit_author_address
'Lei Hou'
;Northwest University
China
;
_audit_update_record             
;
2022-01-13 deposited with the CCDC.	2022-04-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_1_sq                
;
PROBLEM: D-H Bond Without Acceptor  O2W      --H2WB  . Please Check
RESPONSE: This alter is caused by the absence of hydrogen bond acceptor
due to that the solvent molecules was squeezed in refinement.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N Ni O6'
_chemical_formula_weight         272.86

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      trigonal
_space_group_IT_number           163
_space_group_name_H-M_alt        'P -3 1 c'
_space_group_name_Hall           '-P 3 2c'

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

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

_cell_length_a                   18.104(4)
_cell_length_b                   18.104(4)
_cell_length_c                   17.218(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4887(3)
_cell_formula_units_Z            12
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1623
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      21.33

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_F_000             1668
_exptl_transmission_factor_min   0.6318
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.199
_shelx_estimated_absorpt_T_min   0.850
_shelx_estimated_absorpt_T_max   0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24347
_diffrn_reflns_av_unetI/netI     0.0870
_diffrn_reflns_av_R_equivalents  0.1148
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.299
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4054
_reflns_number_gt                2534
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4054
_refine_ls_number_parameters     155
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.934
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.85508(2) 0.41084(2) 0.58318(2) 0.02192(13) Uani 1 1 d . . . . .
O1 O 0.74898(13) 0.29581(13) 0.56432(11) 0.0326(5) Uani 1 1 d . . . . .
O2 O 0.65082(12) 0.18284(12) 0.50050(11) 0.0283(5) Uani 1 1 d . . . . .
O3 O 1.03077(12) 0.48111(14) 0.40380(12) 0.0327(5) Uani 1 1 d . . . . .
O4 O 1.0451(3) 0.4096(3) 0.3074(3) 0.0460(17) Uani 0.530(5) 1 d . . P A 1
O4A O 1.0126(3) 0.4763(3) 0.2768(2) 0.047(2) Uani 0.470(5) 1 d . . P A 2
O1W O 0.79554(14) 0.43585(15) 0.67476(12) 0.0362(6) Uani 1 1 d . . . . .
H1WA H 0.8339 0.4720 0.7048 0.054 Uiso 1 1 d R U . . .
H1WB H 0.7654 0.4564 0.6580 0.054 Uiso 1 1 d R U . . .
O2W O 0.89170(15) 0.34799(15) 0.66369(13) 0.0483(7) Uani 1 1 d . . . . .
H2WA H 0.9398 0.3836 0.6829 0.072 Uiso 1 1 d R U . . .
H2WB H 0.8956 0.3087 0.6405 0.072 Uiso 1 1 d R U . . .
N1 N 0.90625(14) 0.36918(15) 0.49820(13) 0.0245(6) Uani 1 1 d . . . . .
H1A H 0.9584 0.4117 0.4872 0.029 Uiso 1 1 calc R U . . .
H1B H 0.9119 0.3268 0.5179 0.029 Uiso 1 1 calc R U . . .
C1 C 0.72147(18) 0.25118(18) 0.50317(16) 0.0221(6) Uani 1 1 d . . . . .
C2 C 0.77177(19) 0.28066(18) 0.42805(16) 0.0247(7) Uani 1 1 d . . . . .
C3 C 0.85975(18) 0.34019(19) 0.42697(16) 0.0249(7) Uani 1 1 d . . . . .
C4 C 0.90072(19) 0.3693(2) 0.35539(18) 0.0394(9) Uani 1 1 d . . . . .
C5 C 0.8564(2) 0.3353(2) 0.28734(18) 0.0446(10) Uani 1 1 d . . . . .
H5 H 0.8850 0.3542 0.2403 0.054 Uiso 1 1 calc R U . . .
C6 C 0.7701(2) 0.2734(2) 0.28678(17) 0.0343(8) Uani 1 1 d . . . . .
C7 C 0.7291(2) 0.2484(2) 0.35890(17) 0.0321(8) Uani 1 1 d . . . . .
H7 H 0.6710 0.2088 0.3602 0.038 Uiso 1 1 calc R U . . .
C8 C 0.9948(2) 0.4356(3) 0.3495(2) 0.0715(15) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O3 2.026(2) 7_766 ?
Ni1 O1 2.033(2) . ?
Ni1 N1 2.066(2) . ?
Ni1 O2 2.068(2) 2_655 ?
Ni1 O1W 2.083(2) . ?
Ni1 O2W 2.100(2) . ?
O1 C1 1.268(3) . ?
O2 C1 1.260(3) . ?
O2 Ni1 2.068(2) 3_665 ?
O3 C8 1.201(4) . ?
O3 Ni1 2.026(2) 7_766 ?
O4 C8 1.416(6) . ?
O4A C8 1.405(6) . ?
O4A O4A 1.425(10) 6 ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8500 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8500 . ?
N1 C3 1.431(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C1 C2 1.517(4) . ?
C2 C7 1.380(4) . ?
C2 C3 1.408(4) . ?
C3 C4 1.398(4) . ?
C4 C5 1.379(4) . ?
C4 C8 1.519(4) . ?
C5 C6 1.395(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(4) . ?
C6 C6 1.492(6) 4_665 ?
C7 H7 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
O3 Ni1 O1 172.75(9) 7_766 . ?
O3 Ni1 N1 90.21(9) 7_766 . ?
O1 Ni1 N1 83.06(9) . . ?
O3 Ni1 O2 91.53(9) 7_766 2_655 ?
O1 Ni1 O2 91.29(8) . 2_655 ?
N1 Ni1 O2 90.95(9) . 2_655 ?
O3 Ni1 O1W 95.47(9) 7_766 . ?
O1 Ni1 O1W 90.98(9) . . ?
N1 Ni1 O1W 172.14(9) . . ?
O2 Ni1 O1W 94.31(8) 2_655 . ?
O3 Ni1 O2W 90.24(9) 7_766 . ?
O1 Ni1 O2W 86.73(9) . . ?
N1 Ni1 O2W 87.07(10) . . ?
O2 Ni1 O2W 177.36(9) 2_655 . ?
O1W Ni1 O2W 87.48(9) . . ?
C1 O1 Ni1 130.89(19) . . ?
C1 O2 Ni1 124.65(18) . 3_665 ?
C8 O3 Ni1 133.7(2) . 7_766 ?
C8 O4A O4A 152.7(6) . 6 ?
Ni1 O1W H1WA 108.3 . . ?
Ni1 O1W H1WB 110.7 . . ?
H1WA O1W H1WB 109.1 . . ?
Ni1 O2W H2WA 109.1 . . ?
Ni1 O2W H2WB 108.9 . . ?
H2WA O2W H2WB 109.6 . . ?
C3 N1 Ni1 116.88(18) . . ?
C3 N1 H1A 108.1 . . ?
Ni1 N1 H1A 108.1 . . ?
C3 N1 H1B 108.1 . . ?
Ni1 N1 H1B 108.1 . . ?
H1A N1 H1B 107.3 . . ?
O2 C1 O1 122.6(3) . . ?
O2 C1 C2 116.8(2) . . ?
O1 C1 C2 120.6(3) . . ?
C7 C2 C3 119.5(3) . . ?
C7 C2 C1 118.4(3) . . ?
C3 C2 C1 122.1(3) . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 N1 120.9(3) . . ?
C2 C3 N1 120.2(2) . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 C8 117.9(3) . . ?
C3 C4 C8 122.1(3) . . ?
C4 C5 C6 122.2(3) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C7 117.0(3) . . ?
C5 C6 C6 120.9(3) . 4_665 ?
C7 C6 C6 121.8(3) . 4_665 ?
C2 C7 C6 122.2(3) . . ?
C2 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
O3 C8 O4A 115.5(4) . . ?
O3 C8 O4 114.0(4) . . ?
O3 C8 C4 120.0(3) . . ?
O4A C8 C4 110.3(4) . . ?
O4 C8 C4 115.1(4) . . ?

_refine_diff_density_max         0.801
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.085



