# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2264720'
loop_
_audit_author_name
_audit_author_address
'Xiangzhu Wei'
;Technical Institute of Physics and Chemistry
China
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2023-08-15 downloaded from the CCDC.
;

_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            'C10 H19 N Ni O9'
_chemical_formula_weight         355.97

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.2401(3)
_cell_length_b                   7.9797(3)
_cell_length_c                   24.8846(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.433(4)
_cell_angle_gamma                90
_cell_volume                     1431.22(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    180.00(10)
_cell_measurement_reflns_used    5031
_cell_measurement_theta_min      2.6780
_cell_measurement_theta_max      29.3860

_exptl_crystal_description       rod-like
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.400
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.49340
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9069
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.682
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3275
_reflns_number_gt                2863
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0428P)²+0.3442P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3275
_refine_ls_number_parameters     221
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0790
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.002
_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 0.40548(3) 0.56017(3) 0.67376(2) 0.01423(9) Uani 1 1 d . . . . .
O1 O -0.07536(18) 0.29346(17) 0.67395(5) 0.0233(3) Uani 1 1 d . . . . .
O2 O 0.20937(18) 0.38926(17) 0.69637(5) 0.0206(3) Uani 1 1 d . . . . .
O3 O 0.57947(18) 0.71655(16) 0.64037(5) 0.0196(3) Uani 1 1 d . . . . .
O4 O 0.8592(2) 0.88448(18) 0.61146(5) 0.0275(3) Uani 1 1 d . . . . .
O5 O 0.25738(19) 0.75937(17) 0.70428(5) 0.0208(3) Uani 1 1 d D . . . .
H5A H 0.281(3) 0.790(2) 0.7406(6) 0.025 Uiso 1 1 d D U . . .
H5B H 0.129(2) 0.748(3) 0.6992(8) 0.025 Uiso 1 1 d D U . . .
O6 O 0.55390(19) 0.35567(16) 0.64837(5) 0.0202(3) Uani 1 1 d D . . . .
H6A H 0.683(2) 0.353(3) 0.6554(8) 0.024 Uiso 1 1 d D U . . .
H6B H 0.507(3) 0.260(2) 0.6613(8) 0.024 Uiso 1 1 d D U . . .
O7 O 0.5663(2) 0.55144(16) 0.74671(5) 0.0201(3) Uani 1 1 d D . . . .
H7A H 0.593(3) 0.4491(18) 0.7608(8) 0.024 Uiso 1 1 d D U . . .
H7B H 0.564(3) 0.632(2) 0.7730(8) 0.024 Uiso 1 1 d D U . . .
O9 O -0.10958(19) 0.72942(17) 0.71326(6) 0.0214(3) Uani 1 1 d D . . . .
H9A H -0.201(3) 0.731(3) 0.6853(7) 0.026 Uiso 1 1 d D U . . .
H9B H -0.140(3) 0.660(2) 0.7381(7) 0.026 Uiso 1 1 d D U . . .
N1 N 0.2332(2) 0.55586(17) 0.60572(6) 0.0162(3) Uani 1 1 d . . . . .
C1 C 0.0628(3) 0.3768(2) 0.66461(7) 0.0170(4) Uani 1 1 d . . . . .
C2 C 0.0569(3) 0.4717(2) 0.61112(8) 0.0205(4) Uani 1 1 d . . . . .
H2A H 0.0308 0.3939 0.5814 0.025 Uiso 1 1 calc R U . . .
H2B H -0.0421 0.5540 0.6094 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2763(3) 0.5987(2) 0.55902(7) 0.0192(4) Uani 1 1 d . . . . .
H3 H 0.1928 0.5705 0.5297 0.023 Uiso 1 1 calc R U . . .
C4 C 0.4426(3) 0.6869(2) 0.54748(7) 0.0188(4) Uani 1 1 d . . . . .
C5 C 0.4625(3) 0.7203(2) 0.49264(8) 0.0255(4) Uani 1 1 d . . . . .
H5 H 0.3715 0.6831 0.4665 0.031 Uiso 1 1 calc R U . . .
C6 C 0.6110(3) 0.8056(3) 0.47698(8) 0.0306(5) Uani 1 1 d . . . . .
H6 H 0.6212 0.8261 0.4406 0.037 Uiso 1 1 calc R U . . .
C7 C 0.7486(3) 0.8623(3) 0.51619(8) 0.0276(5) Uani 1 1 d . . . . .
H7 H 0.8505 0.9207 0.5058 0.033 Uiso 1 1 calc R U . . .
C8 C 0.7334(3) 0.8318(2) 0.57004(7) 0.0208(4) Uani 1 1 d . . . . .
C9 C 0.5809(3) 0.7410(2) 0.58798(7) 0.0174(4) Uani 1 1 d . . . . .
C10 C 1.0150(3) 0.9769(3) 0.59739(9) 0.0274(5) Uani 1 1 d . . . . .
H10A H 1.0836 0.9107 0.5739 0.041 Uiso 1 1 calc R U . . .
H10B H 1.0932 1.0044 0.6295 0.041 Uiso 1 1 calc R U . . .
H10C H 0.9735 1.0781 0.5792 0.041 Uiso 1 1 calc R U . . .
O8 O 0.5046(2) 0.03662(17) 0.68526(7) 0.0348(4) Uani 1 1 d D . . . .
H8A H 0.401(3) 0.001(3) 0.6987(10) 0.042 Uiso 1 1 d D U . . .
H8B H 0.560(3) -0.045(3) 0.6689(10) 0.042 Uiso 1 1 d 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 N1 2.0060(16) . ?
Ni1 O3 2.0081(12) . ?
Ni1 O7 2.0630(14) . ?
Ni1 O6 2.0846(13) . ?
Ni1 O2 2.0842(13) . ?
Ni1 O5 2.0994(13) . ?
O1 C1 1.241(2) . ?
O2 C1 1.266(2) . ?
O3 C9 1.319(2) . ?
O4 C8 1.375(2) . ?
O4 C10 1.419(2) . ?
O5 H5A 0.936(14) . ?
O5 H5B 0.930(15) . ?
O6 H6A 0.933(15) . ?
O6 H6B 0.910(14) . ?
O7 H7A 0.902(14) . ?
O7 H7B 0.920(14) . ?
O9 H9A 0.916(15) . ?
O9 H9B 0.871(14) . ?
N1 C3 1.278(2) . ?
N1 C2 1.460(2) . ?
C1 C2 1.528(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.447(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.411(3) . ?
C4 C9 1.419(3) . ?
C5 C6 1.361(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.427(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O8 H8A 0.898(15) . ?
O8 H8B 0.885(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 O3 91.48(6) . . ?
N1 Ni1 O7 175.02(6) . . ?
O3 Ni1 O7 93.50(5) . . ?
N1 Ni1 O6 91.60(6) . . ?
O3 Ni1 O6 89.97(5) . . ?
O7 Ni1 O6 88.63(5) . . ?
N1 Ni1 O2 80.30(6) . . ?
O3 Ni1 O2 171.26(5) . . ?
O7 Ni1 O2 94.74(5) . . ?
O6 Ni1 O2 87.33(6) . . ?
N1 Ni1 O5 91.16(6) . . ?
O3 Ni1 O5 92.36(5) . . ?
O7 Ni1 O5 88.41(5) . . ?
O6 Ni1 O5 176.35(5) . . ?
O2 Ni1 O5 90.77(6) . . ?
C1 O2 Ni1 115.80(11) . . ?
C9 O3 Ni1 124.38(11) . . ?
C8 O4 C10 117.35(15) . . ?
Ni1 O5 H5A 119.8(13) . . ?
Ni1 O5 H5B 114.6(13) . . ?
H5A O5 H5B 104.1(15) . . ?
Ni1 O6 H6A 119.7(13) . . ?
Ni1 O6 H6B 109.3(13) . . ?
H6A O6 H6B 108.4(16) . . ?
Ni1 O7 H7A 116.9(14) . . ?
Ni1 O7 H7B 123.8(13) . . ?
H7A O7 H7B 112.1(17) . . ?
H9A O9 H9B 109.6(17) . . ?
C3 N1 C2 119.83(16) . . ?
C3 N1 Ni1 125.25(14) . . ?
C2 N1 Ni1 114.18(11) . . ?
O1 C1 O2 124.61(17) . . ?
O1 C1 C2 118.16(16) . . ?
O2 C1 C2 117.23(16) . . ?
N1 C2 C1 110.82(15) . . ?
N1 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N1 C3 C4 126.14(17) . . ?
N1 C3 H3 116.9 . . ?
C4 C3 H3 116.9 . . ?
C5 C4 C9 119.98(18) . . ?
C5 C4 C3 116.53(17) . . ?
C9 C4 C3 123.48(16) . . ?
C6 C5 C4 121.81(19) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 119.41(18) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 120.24(19) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
O4 C8 C7 124.56(18) . . ?
O4 C8 C9 113.44(16) . . ?
C7 C8 C9 122.00(18) . . ?
O3 C9 C4 125.86(17) . . ?
O3 C9 C8 117.59(16) . . ?
C4 C9 C8 116.55(16) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H8A O8 H8B 111.7(19) . . ?

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 O1 -173.08(14) . . . . ?
Ni1 O2 C1 C2 6.9(2) . . . . ?
C3 N1 C2 C1 159.29(16) . . . . ?
Ni1 N1 C2 C1 -11.36(18) . . . . ?
O1 C1 C2 N1 -177.24(15) . . . . ?
O2 C1 C2 N1 2.8(2) . . . . ?
C2 N1 C3 C4 178.06(17) . . . . ?
Ni1 N1 C3 C4 -12.4(3) . . . . ?
N1 C3 C4 C5 179.54(18) . . . . ?
N1 C3 C4 C9 -1.3(3) . . . . ?
C9 C4 C5 C6 -0.7(3) . . . . ?
C3 C4 C5 C6 178.54(18) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C10 O4 C8 C7 0.2(3) . . . . ?
C10 O4 C8 C9 -179.61(17) . . . . ?
C6 C7 C8 O4 -178.93(19) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
Ni1 O3 C9 C4 12.0(3) . . . . ?
Ni1 O3 C9 C8 -168.88(12) . . . . ?
C5 C4 C9 O3 -179.46(17) . . . . ?
C3 C4 C9 O3 1.4(3) . . . . ?
C5 C4 C9 C8 1.5(3) . . . . ?
C3 C4 C9 C8 -177.73(17) . . . . ?
O4 C8 C9 O3 -0.9(2) . . . . ?
C7 C8 C9 O3 179.29(18) . . . . ?
O4 C8 C9 C4 178.24(16) . . . . ?
C7 C8 C9 C4 -1.5(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
O5 H5A O2 0.936(14) 1.752(16) 2.6704(19) 166.2(19) 2_556
O5 H5B O9 0.930(15) 1.802(16) 2.6978(19) 161.0(18) .
O6 H6A O1 0.933(15) 1.831(16) 2.7446(19) 165.6(18) 1_655
O6 H6B O8 0.910(14) 1.878(16) 2.7412(19) 157.7(18) .
O7 H7A O9 0.902(14) 1.868(14) 2.7630(18) 171(2) 2_546
O7 H7B O1 0.920(14) 1.839(15) 2.7582(18) 177(2) 2_556
O9 H9A O3 0.916(15) 1.856(16) 2.7560(19) 167.0(19) 1_455
O9 H9A O4 0.916(15) 2.285(18) 2.8092(19) 116.0(16) 1_455
O9 H9B O7 0.871(14) 2.33(2) 2.9301(19) 126.4(17) 1_455
O9 H9B O8 0.871(14) 2.284(16) 2.993(2) 138.6(18) 2_556
O8 H8A O5 0.898(15) 2.20(2) 2.912(2) 136(2) 1_545
O8 H8B O3 0.885(15) 2.038(18) 2.8601(19) 154(2) 1_545

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.092



