# 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 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_200423f1b1_96k_r
_database_code_depnum_ccdc_archive 'CCDC 1986126'
loop_
_audit_author_name
_audit_author_address
'Wataru Fujita'
;Seikei University
Japan
;
_audit_update_record             
;
2020-05-22 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H6 Ni O6'
_chemical_formula_weight         208.80

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'
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           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                   5.1199(14)
_cell_length_b                   7.5123(19)
_cell_length_c                   8.657(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.148(4)
_cell_angle_gamma                90
_cell_volume                     321.40(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    96(1)
_cell_measurement_reflns_used    984
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      27.50

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.158
_exptl_crystal_F_000             212
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    2.996
_shelx_estimated_absorpt_T_min   0.586
_shelx_estimated_absorpt_T_max   0.586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.441
_exptl_absorpt_correction_T_max  0.549
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      96(1)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            3571
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.647
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             735
_reflns_number_gt                687
_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       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    CrystalStructure
_computing_publication_material  CrystalStructure
_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)+(0.0157P)²+0.2788P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         735
_refine_ls_number_parameters     64
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0206
_refine_ls_wR_factor_ref         0.0484
_refine_ls_wR_factor_gt          0.0475
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_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 0.500000 0.500000 0.500000 0.00562(11) Uani 1 2 d S . P . .
O2 O 0.4666(2) 0.34527(17) 0.68346(14) 0.0082(3) Uani 1 1 d . . . . .
O3 O 0.7651(3) 0.30254(17) 0.48404(15) 0.0086(3) Uani 1 1 d . . . . .
H3 H 0.890(5) 0.324(4) 0.446(3) 0.029(7) Uiso 1 1 d . . . . .
O4 O 0.6746(2) 0.13933(17) 0.85424(14) 0.0088(3) Uani 1 1 d . . . . .
C5 C 0.6485(3) 0.2304(2) 0.7275(2) 0.0078(3) Uani 1 1 d . . . . .
C6 C 0.8439(4) 0.1973(3) 0.6257(2) 0.0121(4) Uani 1 1 d . . . . .
H6A H 1.017(5) 0.236(3) 0.692(3) 0.021(6) Uiso 1 1 d . . . . .
H6B H 0.839(5) 0.064(3) 0.598(3) 0.019(6) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.00479(17) 0.00683(18) 0.00506(17) 0.00030(11) 0.00100(11) 0.00019(11)
O2 0.0067(6) 0.0098(6) 0.0084(6) 0.0010(5) 0.0027(4) 0.0010(5)
O3 0.0077(6) 0.0114(7) 0.0080(6) 0.0033(5) 0.0042(5) 0.0014(5)
O4 0.0072(6) 0.0124(6) 0.0070(6) 0.0027(5) 0.0020(4) 0.0015(5)
C5 0.0059(8) 0.0093(8) 0.0077(8) -0.0019(7) 0.0005(6) -0.0029(6)
C6 0.0120(9) 0.0166(10) 0.0091(9) 0.0060(7) 0.0051(7) 0.0057(7)

_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 2.0112(13) . ?
Ni1 O2 2.0112(13) 3_666 ?
Ni1 O3 2.0396(13) 3_666 ?
Ni1 O3 2.0396(13) . ?
Ni1 O4 2.0894(12) 4_565 ?
Ni1 O4 2.0894(12) 2_656 ?
O2 C5 1.254(2) . ?
O3 C6 1.426(2) . ?
O3 H3 0.81(3) . ?
O4 C5 1.270(2) . ?
C5 C6 1.517(3) . ?
C6 H6A 0.97(2) . ?
C6 H6B 1.03(2) . ?

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 180.0 . 3_666 ?
O2 Ni1 O3 99.87(5) . 3_666 ?
O2 Ni1 O3 80.13(5) 3_666 3_666 ?
O2 Ni1 O3 80.13(5) . . ?
O2 Ni1 O3 99.87(5) 3_666 . ?
O3 Ni1 O3 180.0 3_666 . ?
O2 Ni1 O4 88.19(5) . 4_565 ?
O2 Ni1 O4 91.81(5) 3_666 4_565 ?
O3 Ni1 O4 88.02(5) 3_666 4_565 ?
O3 Ni1 O4 91.98(5) . 4_565 ?
O2 Ni1 O4 91.81(5) . 2_656 ?
O2 Ni1 O4 88.19(5) 3_666 2_656 ?
O3 Ni1 O4 91.98(5) 3_666 2_656 ?
O3 Ni1 O4 88.02(5) . 2_656 ?
O4 Ni1 O4 180.0 4_565 2_656 ?
C5 O2 Ni1 115.35(11) . . ?
C6 O3 Ni1 112.87(11) . . ?
C6 O3 H3 112.4(19) . . ?
Ni1 O3 H3 119.8(19) . . ?
C5 O4 Ni1 132.74(11) . 2_646 ?
O2 C5 O4 122.37(16) . . ?
O2 C5 C6 119.12(15) . . ?
O4 C5 C6 118.51(15) . . ?
O3 C6 C5 109.12(14) . . ?
O3 C6 H6A 110.5(14) . . ?
C5 C6 H6A 104.4(14) . . ?
O3 C6 H6B 110.8(14) . . ?
C5 C6 H6B 108.3(13) . . ?
H6A C6 H6B 113.4(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 C5 O4 170.55(12) . . . . ?
Ni1 O2 C5 C6 -10.0(2) . . . . ?
Ni1 O4 C5 O2 -158.47(12) 2_646 . . . ?
Ni1 O4 C5 C6 22.1(2) 2_646 . . . ?
Ni1 O3 C6 C5 15.80(18) . . . . ?
O2 C5 C6 O3 -4.2(2) . . . . ?
O4 C5 C6 O3 175.32(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O4 0.81(3) 1.86(3) 2.6606(18) 177(3) 4_665 yes

_refine_diff_density_max         0.347
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.080

_shelx_res_file                  
;
TITL 200423f1b1
    shelx.res
    created by SHELXL-2018/3 at 10:05:22 on 30-Apr-2020
CELL  0.71075 5.11990 7.51230 8.65700 90.00000 105.14800 90.00000
ZERR  2 0.00140 0.00190 0.00200 0.00000 0.00400 0.00000
LATT 1
SYMM .50-X, .50+Y, .50-Z
SFAC C H NI O
UNIT 8 12 2 12
L.S. 20
FMAP 2
PLAN 25
WPDB -2
EQIV $1 x+1/2, -y+1/2, z-1/2
HTAB O3 O4_$1
BOND $H
CONF
LIST 4
TEMP -177
ACTA
SIZE 0.20 0.20 0.20
WGHT    0.015700    0.278800
FVAR       1.20805
NI1   3    0.500000    0.500000    0.500000    10.50000    0.00479    0.00683 =
         0.00506    0.00030    0.00100    0.00019
O2    4    0.466570    0.345267    0.683457    11.00000    0.00667    0.00983 =
         0.00844    0.00095    0.00267    0.00103
O3    4    0.765118    0.302543    0.484036    11.00000    0.00769    0.01140 =
         0.00804    0.00332    0.00418    0.00138
H3    2    0.890050    0.323645    0.446314    11.00000    0.02924
O4    4    0.674551    0.139330    0.854236    11.00000    0.00720    0.01236 =
         0.00705    0.00270    0.00203    0.00154
C5    1    0.648548    0.230448    0.727524    11.00000    0.00588    0.00926 =
         0.00766   -0.00186    0.00054   -0.00294
C6    1    0.843933    0.197322    0.625719    11.00000    0.01198    0.01664 =
         0.00908    0.00600    0.00507    0.00569
H6A   2    1.017281    0.236381    0.691864    11.00000    0.02134
H6B   2    0.838823    0.063878    0.598071    11.00000    0.01898
HKLF 4




REM  200423f1b1
REM wR2 = 0.0484, GooF = S = 1.055, Restrained GooF = 1.055 for all data
REM R1 = 0.0206 for 687 Fo > 4sig(Fo) and 0.0230 for all 735 data
REM 64 parameters refined using 0 restraints

END

WGHT      0.0157      0.2796

REM Highest difference peak  0.347,  deepest hole -0.485,  1-sigma level  0.080
Q1    1   0.7539  0.2125  0.6738  11.00000  0.05    0.35
Q2    1   0.4370  0.3638  0.5495  11.00000  0.05    0.27
Q3    1   0.8212  0.3588  0.6459  11.00000  0.05    0.27
Q4    1   0.7173  0.1847  1.0047  11.00000  0.05    0.26
Q5    1   0.4320  0.0065  0.6374  11.00000  0.05    0.25
Q6    1   0.8271 -0.1359  0.5586  11.00000  0.05    0.24
Q7    1   0.4637  0.5026  0.3804  11.00000  0.05    0.23
Q8    1   0.7913  0.1801  0.4836  11.00000  0.05    0.23
Q9    1   0.3671  0.4284  0.8108  11.00000  0.05    0.22
Q10   1   0.7554  0.0998  0.8898  11.00000  0.05    0.22
Q11   1   0.4417  0.6292  0.5438  11.00000  0.05    0.22
Q12   1   0.6026  0.1948  0.9114  11.00000  0.05    0.22
Q13   1   0.5081  0.4233  0.6464  11.00000  0.05    0.22
Q14   1   0.5303  0.2635  0.6902  11.00000  0.05    0.21
Q15   1   0.3850  0.3417  0.6881  11.00000  0.05    0.20
Q16   1   0.7075  0.1983  0.8215  11.00000  0.05    0.20
Q17   1   0.8945  0.1159  0.6156  11.00000  0.05    0.20
Q18   1   1.0369  0.1746  0.6621  11.00000  0.05    0.20
Q19   1   0.7946  0.2546  0.5620  11.00000  0.05    0.20
Q20   1   0.9130 -0.0623  0.4931  11.00000  0.05    0.18
Q21   1   1.1893  0.1634  0.5551  11.00000  0.05    0.18
Q22   1   0.7431  0.2358  0.8855  11.00000  0.05    0.18
Q23   1   0.8519  0.0179  0.7430  11.00000  0.05    0.17
Q24   1   0.6779  0.2438  0.4420  11.00000  0.05    0.17
Q25   1   0.4734  0.3629  0.7700  11.00000  0.05    0.17
;
_shelx_res_checksum              28437
####################################################################### 
# 
# 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_200422f1a_299k_r
_database_code_depnum_ccdc_archive 'CCDC 1986127'
loop_
_audit_author_name
_audit_author_address
'Wataru Fujita'
;Seikei University
Japan
;
_audit_update_record             
;
2020-05-22 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H6 Ni O6'
_chemical_formula_weight         208.80

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'
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           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                   5.1389(17)
_cell_length_b                   7.650(2)
_cell_length_c                   8.618(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.413(5)
_cell_angle_gamma                90
_cell_volume                     326.61(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    299(1)
_cell_measurement_reflns_used    1057
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      27.50

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.123
_exptl_crystal_F_000             212
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    2.948
_shelx_estimated_absorpt_T_min   0.590
_shelx_estimated_absorpt_T_max   0.590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_T_max  0.555
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(1)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            3560
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.621
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             740
_reflns_number_gt                681
_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       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    CrystalStructure
_computing_publication_material  CrystalStructure
_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)+(0.0316P)²+0.0950P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         740
_refine_ls_number_parameters     64
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0209
_refine_ls_wR_factor_ref         0.0594
_refine_ls_wR_factor_gt          0.0586
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.000
_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 0.500000 0.500000 0.500000 0.01241(14) Uani 1 2 d S . P . .
O2 O 0.4751(2) 0.34959(16) 0.68726(15) 0.0178(3) Uani 1 1 d . . . . .
O3 O 0.7728(3) 0.31001(17) 0.48732(15) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.929(7) 0.322(4) 0.445(4) 0.061(9) Uiso 1 1 d . . . . .
O4 O 0.6800(2) 0.14460(18) 0.85542(15) 0.0200(3) Uani 1 1 d . . . . .
C5 C 0.6545(3) 0.2359(2) 0.7300(2) 0.0153(4) Uani 1 1 d . . . . .
C6 C 0.8479(4) 0.2046(3) 0.6275(3) 0.0283(5) Uani 1 1 d . . . . .
H6A H 1.013(6) 0.242(4) 0.695(3) 0.048(8) Uiso 1 1 d . . . . .
H6B H 0.835(6) 0.067(4) 0.591(4) 0.056(8) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.0117(2) 0.0148(2) 0.0110(2) 0.00079(10) 0.00360(13) 0.00025(10)
O2 0.0169(6) 0.0211(6) 0.0176(6) 0.0046(5) 0.0083(5) 0.0045(5)
O3 0.0183(6) 0.0246(7) 0.0157(6) 0.0057(5) 0.0094(5) 0.0056(5)
O4 0.0174(6) 0.0274(7) 0.0169(6) 0.0089(5) 0.0075(5) 0.0062(5)
C5 0.0124(8) 0.0190(9) 0.0143(8) 0.0004(7) 0.0031(6) -0.0017(6)
C6 0.0268(11) 0.0377(12) 0.0261(11) 0.0167(9) 0.0172(9) 0.0144(9)

_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 2.0137(13) . ?
Ni1 O2 2.0137(13) 3_666 ?
Ni1 O3 2.0423(13) 3_666 ?
Ni1 O3 2.0423(13) . ?
Ni1 O4 2.0956(13) 4_565 ?
Ni1 O4 2.0956(13) 2_656 ?
O2 C5 1.250(2) . ?
O3 C6 1.418(2) . ?
O3 H3 0.97(3) . ?
O4 C5 1.264(2) . ?
C5 C6 1.514(3) . ?
C6 H6A 0.94(3) . ?
C6 H6B 1.09(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(9) . 3_666 ?
O2 Ni1 O3 99.96(5) . 3_666 ?
O2 Ni1 O3 80.04(5) 3_666 3_666 ?
O2 Ni1 O3 80.04(5) . . ?
O2 Ni1 O3 99.96(5) 3_666 . ?
O3 Ni1 O3 180.0 3_666 . ?
O2 Ni1 O4 88.16(5) . 4_565 ?
O2 Ni1 O4 91.84(5) 3_666 4_565 ?
O3 Ni1 O4 88.06(6) 3_666 4_565 ?
O3 Ni1 O4 91.94(6) . 4_565 ?
O2 Ni1 O4 91.84(5) . 2_656 ?
O2 Ni1 O4 88.16(5) 3_666 2_656 ?
O3 Ni1 O4 91.94(6) 3_666 2_656 ?
O3 Ni1 O4 88.06(6) . 2_656 ?
O4 Ni1 O4 180.0 4_565 2_656 ?
C5 O2 Ni1 115.77(11) . . ?
C6 O3 Ni1 113.23(11) . . ?
C6 O3 H3 108(2) . . ?
Ni1 O3 H3 126.8(19) . . ?
C5 O4 Ni1 133.37(12) . 2_646 ?
O2 C5 O4 122.50(16) . . ?
O2 C5 C6 119.04(15) . . ?
O4 C5 C6 118.46(16) . . ?
O3 C6 C5 109.57(15) . . ?
O3 C6 H6A 110.4(18) . . ?
C5 C6 H6A 102.7(18) . . ?
O3 C6 H6B 108.8(18) . . ?
C5 C6 H6B 108.7(17) . . ?
H6A C6 H6B 116(2) . . ?

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 C5 O4 172.60(13) . . . . ?
Ni1 O2 C5 C6 -8.0(2) . . . . ?
Ni1 O4 C5 O2 -159.60(13) 2_646 . . . ?
Ni1 O4 C5 C6 21.0(3) 2_646 . . . ?
Ni1 O3 C6 C5 13.4(2) . . . . ?
O2 C5 C6 O3 -3.9(3) . . . . ?
O4 C5 C6 O3 175.58(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O4 0.97(3) 1.69(3) 2.6563(19) 174(3) 4_665 yes

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.108

_shelx_res_file                  
;
TITL 200422f1a
    shelx.res
    created by SHELXL-2018/3 at 09:57:11 on 30-Apr-2020
CELL  0.71075 5.13890 7.65000 8.61800 90.000 105.413 90.000
ZERR  2 0.00170 0.00200 0.00300 0.000 0.005 0.000
LATT 1
SYMM .50-X, .50+Y, .50-Z
SFAC C H NI O
UNIT 8 12 2 12
L.S. 20
FMAP 2
PLAN 25
WPDB -2
EQIV $1 x+1/2, -y+1/2, z-1/2
HTAB O3 O4_$1
BOND $H
CONF
LIST 4
TEMP 26.0
ACTA
SIZE 0.20 0.20 0.20
WGHT    0.031600    0.095000
FVAR       1.39393
NI1   3    0.500000    0.500000    0.500000    10.50000    0.01171    0.01484 =
         0.01100    0.00079    0.00360    0.00025
O2    4    0.475051    0.349587    0.687260    11.00000    0.01694    0.02109 =
         0.01763    0.00457    0.00828    0.00452
O3    4    0.772792    0.310007    0.487318    11.00000    0.01835    0.02456 =
         0.01572    0.00567    0.00943    0.00561
H3    2    0.929127    0.322429    0.444884    11.00000    0.06102
O4    4    0.679983    0.144597    0.855416    11.00000    0.01741    0.02743 =
         0.01691    0.00888    0.00747    0.00622
C5    1    0.654506    0.235922    0.730027    11.00000    0.01237    0.01897 =
         0.01426    0.00038    0.00311   -0.00173
C6    1    0.847874    0.204591    0.627493    11.00000    0.02685    0.03773 =
         0.02609    0.01668    0.01720    0.01439
H6A   2    1.013322    0.242070    0.694555    11.00000    0.04764
H6B   2    0.835340    0.067187    0.591393    11.00000    0.05568
HKLF 4




REM  200422f1a
REM wR2 = 0.0594, GooF = S = 1.148, Restrained GooF = 1.148 for all data
REM R1 = 0.0209 for 681 Fo > 4sig(Fo) and 0.0229 for all 740 data
REM 64 parameters refined using 0 restraints

END

WGHT      0.0318      0.0928

REM Highest difference peak  0.326,  deepest hole -0.551,  1-sigma level  0.108
Q1    1   0.9395  0.1030  0.6331  11.00000  0.05    0.33
Q2    1   1.0267  0.1750  0.6695  11.00000  0.05    0.31
Q3    1   0.7502  0.2046  0.6748  11.00000  0.05    0.26
Q4    1   0.8557  0.3252  0.4433  11.00000  0.05    0.25
Q5    1   1.0356  0.3347  0.7083  11.00000  0.05    0.24
Q6    1   1.2176  0.0067  0.6349  11.00000  0.05    0.22
Q7    1   0.9925 -0.0749  0.5941  11.00000  0.05    0.21
Q8    1   1.0621  0.1123  0.5249  11.00000  0.05    0.21
Q9    1   0.7249  0.0065  0.4456  11.00000  0.05    0.20
Q10   1   0.7199  0.0750  0.5489  11.00000  0.05    0.19
Q11   1   0.8080  0.2429  0.5699  11.00000  0.05    0.19
Q12   1   1.1814  0.0909  0.6394  11.00000  0.05    0.19
Q13   1   0.7955  0.0962  0.3990  11.00000  0.05    0.18
Q14   1   0.9689  0.0038  0.5018  11.00000  0.05    0.18
Q15   1   0.8488 -0.0676  0.5389  11.00000  0.05    0.18
Q16   1   1.2480  0.2506  0.8042  11.00000  0.05    0.17
Q17   1   0.5858  0.0114  0.3785  11.00000  0.05    0.17
Q18   1   0.3818  0.3667  0.6934  11.00000  0.05    0.17
Q19   1   1.2198  0.3801  0.8388  11.00000  0.05    0.17
Q20   1   0.4855  0.3390  0.8132  11.00000  0.05    0.16
Q21   1   0.2856  0.2668  0.7247  11.00000  0.05    0.16
Q22   1   0.8344  0.1235  0.4950  11.00000  0.05    0.16
Q23   1   0.2744  0.3703  0.7807  11.00000  0.05    0.16
Q24   1   1.1548  0.2534  0.6634  11.00000  0.05    0.15
Q25   1   1.1274  0.2045  0.4488  11.00000  0.05    0.14
;
_shelx_res_checksum              16032
