# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_ni_sq
_database_code_depnum_ccdc_archive 'CCDC 2069182'
loop_
_audit_author_name
_audit_author_address
'Lei Hou'
;Northwest University
China
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT341_ni_sq               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.016 Ang.
RESPONSE: This alter shows the low bond precision, which may be caused by the disordered solvent molecules, and the restrictions in structural refinement.
;
# Added during the CSD deposition process: Wednesday 10 March 2021 03:17 AM
# 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            'C14 H11 F N4 Ni O1.50'
_chemical_formula_weight         336.98

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           26
_space_group_name_H-M_alt        'P m c 21'
_space_group_name_Hall           'P 2c -2'

_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, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'

_cell_length_a                   11.343(3)
_cell_length_b                   12.587(3)
_cell_length_c                   13.755(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1963.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1120
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      23.42

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   0.6253
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.001
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.915
_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            10368
_diffrn_reflns_av_unetI/netI     0.0945
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.962
_diffrn_reflns_theta_max         25.986
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3970
_reflns_number_gt                2551
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_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          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0555P)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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3970
_refine_ls_number_parameters     224
_refine_ls_number_restraints     104
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1312
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      1.037
_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 0.5000 1.0032(2) 0.6095(2) 0.0199(3) Uani 1 2 d S T P . .
Ni2 Ni 0.5000 0.08627(9) 0.3594(2) 0.0200(3) Uani 1 2 d S T P . .
F1 F 0.5000 0.9715(7) 0.4645(6) 0.029(3) Uani 1 2 d S T P . .
O1 O 0.5000 0.2135(7) 0.4479(7) 0.032(3) Uani 1 2 d S TU P . .
F2 F 0.5000 -0.0224(7) 0.2559(7) 0.025(3) Uani 1 2 d S T P . .
O2 O 0.5000 0.1648(10) 0.5968(10) 0.043(4) Uani 1 2 d S TU P . .
N1 N 0.5000 0.7629(7) 0.5860(7) 0.027(2) Uani 1 2 d DS TU P . .
N2 N 0.5000 0.8377(11) 0.6386(10) 0.027(3) Uani 1 2 d S TU P . .
N4 N 0.5000 0.7047(8) 0.7369(10) 0.045(3) Uani 1 2 d S TU P . .
N5 N 0.6859(5) 1.0052(8) 0.6115(12) 0.0266(14) Uani 1 1 d . . . . .
N6 N 0.6863(5) 0.0893(4) 0.3602(12) 0.0276(13) Uani 1 1 d . . . . .
N3 N 0.5000 0.8085(9) 0.7366(12) 0.045(3) Uani 1 2 d S TU P . .
C1 C 0.5000 0.6739(11) 0.6447(10) 0.030(4) Uani 1 2 d DS T P . .
C2 C 0.5000 0.5620(10) 0.6183(9) 0.049(4) Uani 1 2 d DS T P . .
C3 C 0.5000 0.5319(12) 0.5225(11) 0.064(6) Uani 1 2 d DS TU P . .
H3 H 0.5000 0.5848 0.4752 0.077 Uiso 1 2 calc R U P . .
C4 C 0.5000 0.4262(9) 0.4922(9) 0.046(4) Uani 1 2 d DS TU P . .
H4 H 0.5000 0.4095 0.4264 0.056 Uiso 1 2 calc R U P . .
C5 C 0.5000 0.3458(12) 0.5622(10) 0.037(4) Uani 1 2 d DS TU P . .
C6 C 0.5000 0.3804(10) 0.6557(10) 0.052(4) Uani 1 2 d DS TU P . .
H6 H 0.5000 0.3273 0.7027 0.063 Uiso 1 2 calc R U P . .
C7 C 0.5000 0.4813(9) 0.6902(12) 0.045(4) Uani 1 2 d DS TU P . .
H7 H 0.5000 0.4966 0.7564 0.054 Uiso 1 2 calc R U P . .
C8 C 0.5000 0.2336(11) 0.5313(12) 0.036(3) Uani 1 2 d S TU P . .
C9 C 0.7529(16) 0.9188(9) 0.5973(17) 0.062(6) Uani 1 1 d . . . . .
H9 H 0.7125 0.8553 0.5881 0.074 Uiso 1 1 calc R U . . .
C10 C 0.8769(14) 0.9125(8) 0.5944(15) 0.046(5) Uani 1 1 d . . . . .
H10 H 0.9163 0.8500 0.5787 0.055 Uiso 1 1 calc R U . . .
C11 C 0.9357(6) 1.0050(10) 0.6164(13) 0.027(2) Uani 1 1 d . . . . .
C12 C 0.8608(16) 1.0954(8) 0.6241(15) 0.059(6) Uani 1 1 d . . . . .
H12 H 0.8968 1.1617 0.6274 0.070 Uiso 1 1 calc R U . . .
C13 C 0.7458(12) 1.0928(8) 0.6270(13) 0.037(4) Uani 1 1 d . U . . .
H13 H 0.7049 1.1551 0.6404 0.045 Uiso 1 1 calc R U . . .
C14 C 0.7495(6) 0.0005(6) 0.3620(18) 0.038(2) Uani 1 1 d . . . . .
H14 H 0.7103 -0.0640 0.3686 0.045 Uiso 1 1 calc R U . . .
C15 C 0.8692(7) -0.0001(6) 0.3546(18) 0.041(2) Uani 1 1 d . . . . .
H15 H 0.9079 -0.0644 0.3446 0.049 Uiso 1 1 calc R U . . .
C16 C 0.9339(6) 0.0906(5) 0.3615(14) 0.0292(17) Uani 1 1 d . . . . .
C17 C 0.8679(6) 0.1840(6) 0.3603(17) 0.048(2) Uani 1 1 d . . . . .
H17 H 0.9065 0.2491 0.3582 0.057 Uiso 1 1 calc R U . . .
C18 C 0.7471(6) 0.1815(6) 0.3622(15) 0.046(3) Uani 1 1 d . . . . .
H18 H 0.7058 0.2452 0.3651 0.055 Uiso 1 1 calc R U . . .
O1W O 0.5000 0.7845(7) 0.3595(15) 0.107(4) Uani 1 2 d S TU P . .
H1W1 H 0.5000 0.8239 0.4097 0.161 Uiso 1 2 d R U P . .
H1W2 H 0.5000 0.8255 0.3103 0.161 Uiso 1 2 d R U P . .


_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 F2 2.027(11) 2_665 ?
Ni1 F1 2.035(10) . ?
Ni1 O2 2.042(14) 1_565 ?
Ni1 N5 2.109(5) . ?
Ni1 N5 2.109(5) 4_655 ?
Ni1 N2 2.121(15) . ?
Ni2 F2 1.975(10) . ?
Ni2 O1 2.011(9) . ?
Ni2 F1 2.043(9) 1_545 ?
Ni2 N6 2.114(5) 4_655 ?
Ni2 N6 2.114(5) . ?
Ni2 N3 2.146(16) 2_664 ?
F1 Ni2 2.043(9) 1_565 ?
O1 C8 1.175(17) . ?
F2 Ni1 2.027(11) 2_664 ?
O2 C8 1.250(18) . ?
O2 Ni1 2.042(14) 1_545 ?
N1 N2 1.187(15) . ?
N1 C1 1.381(11) . ?
N2 N3 1.398(19) . ?
N4 N3 1.307(15) . ?
N4 C1 1.326(18) . ?
N5 C13 1.312(12) . ?
N5 C9 1.341(15) . ?
N6 C14 1.328(8) . ?
N6 C18 1.349(8) . ?
N3 Ni2 2.146(16) 2_665 ?
C1 C2 1.454(18) . ?
C2 C3 1.372(12) . ?
C2 C7 1.418(12) . ?
C3 C4 1.394(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.358(12) . ?
C5 C8 1.474(18) . ?
C6 C7 1.357(12) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 C10 1.41(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(16) . ?
C10 H10 0.9300 . ?
C11 C12 1.423(16) . ?
C11 C11 1.459(14) 4_755 ?
C12 C13 1.31(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.363(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.361(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(9) . ?
C16 C16 1.500(13) 4_755 ?
C17 C18 1.371(9) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
O1W H1W1 0.8499 . ?
O1W H1W2 0.8501 . ?

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
F2 Ni1 F1 175.5(5) 2_665 . ?
F2 Ni1 O2 88.1(5) 2_665 1_565 ?
F1 Ni1 O2 96.4(5) . 1_565 ?
F2 Ni1 N5 89.2(4) 2_665 . ?
F1 Ni1 N5 90.9(4) . . ?
O2 Ni1 N5 89.4(3) 1_565 . ?
F2 Ni1 N5 89.2(4) 2_665 4_655 ?
F1 Ni1 N5 90.9(4) . 4_655 ?
O2 Ni1 N5 89.4(3) 1_565 4_655 ?
N5 Ni1 N5 178.0(8) . 4_655 ?
F2 Ni1 N2 86.0(5) 2_665 . ?
F1 Ni1 N2 89.5(5) . . ?
O2 Ni1 N2 174.0(7) 1_565 . ?
N5 Ni1 N2 90.5(3) . . ?
N5 Ni1 N2 90.5(3) 4_655 . ?
F2 Ni2 O1 171.1(4) . . ?
F2 Ni2 F1 91.18(19) . 1_545 ?
O1 Ni2 F1 97.8(4) . 1_545 ?
F2 Ni2 N6 90.9(4) . 4_655 ?
O1 Ni2 N6 89.0(3) . 4_655 ?
F1 Ni2 N6 90.6(3) 1_545 4_655 ?
F2 Ni2 N6 90.9(4) . . ?
O1 Ni2 N6 89.0(3) . . ?
F1 Ni2 N6 90.6(3) 1_545 . ?
N6 Ni2 N6 177.8(4) 4_655 . ?
F2 Ni2 N3 81.9(5) . 2_664 ?
O1 Ni2 N3 89.1(5) . 2_664 ?
F1 Ni2 N3 173.1(5) 1_545 2_664 ?
N6 Ni2 N3 89.6(4) 4_655 2_664 ?
N6 Ni2 N3 89.6(4) . 2_664 ?
Ni1 F1 Ni2 123.7(5) . 1_565 ?
C8 O1 Ni2 139.7(10) . . ?
Ni2 F2 Ni1 129.3(5) . 2_664 ?
C8 O2 Ni1 138.8(12) . 1_545 ?
N2 N1 C1 106.7(11) . . ?
N1 N2 N3 112.3(12) . . ?
N1 N2 Ni1 131.6(11) . . ?
N3 N2 Ni1 116.1(9) . . ?
N3 N4 C1 106.9(13) . . ?
C13 N5 C9 114.3(7) . . ?
C13 N5 Ni1 122.0(8) . . ?
C9 N5 Ni1 123.7(9) . . ?
C14 N6 C18 116.6(6) . . ?
C14 N6 Ni2 121.6(5) . . ?
C18 N6 Ni2 121.8(5) . . ?
N4 N3 N2 105.4(13) . . ?
N4 N3 Ni2 128.0(12) . 2_665 ?
N2 N3 Ni2 126.7(9) . 2_665 ?
N4 C1 N1 108.7(11) . . ?
N4 C1 C2 121.5(12) . . ?
N1 C1 C2 129.8(12) . . ?
C3 C2 C7 118.2(13) . . ?
C3 C2 C1 120.5(12) . . ?
C7 C2 C1 121.3(10) . . ?
C2 C3 C4 123.4(14) . . ?
C2 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C3 C4 C5 119.1(13) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 114.8(14) . . ?
C6 C5 C8 125.5(13) . . ?
C4 C5 C8 119.7(12) . . ?
C7 C6 C5 129.2(16) . . ?
C7 C6 H6 115.4 . . ?
C5 C6 H6 115.4 . . ?
C6 C7 C2 115.3(14) . . ?
C6 C7 H7 122.4 . . ?
C2 C7 H7 122.4 . . ?
O1 C8 O2 123.7(14) . . ?
O1 C8 C5 119.2(12) . . ?
O2 C8 C5 117.1(14) . . ?
N5 C9 C10 127.9(11) . . ?
N5 C9 H9 116.0 . . ?
C10 C9 H9 116.0 . . ?
C11 C10 C9 115.5(10) . . ?
C11 C10 H10 122.3 . . ?
C9 C10 H10 122.3 . . ?
C10 C11 C12 113.8(8) . . ?
C10 C11 C11 119.0(7) . 4_755 ?
C12 C11 C11 126.6(8) . 4_755 ?
C13 C12 C11 125.3(12) . . ?
C13 C12 H12 117.3 . . ?
C11 C12 H12 117.3 . . ?
C12 C13 N5 122.2(11) . . ?
C12 C13 H13 118.9 . . ?
N5 C13 H13 118.9 . . ?
N6 C14 C15 122.7(7) . . ?
N6 C14 H14 118.6 . . ?
C15 C14 H14 118.6 . . ?
C16 C15 C14 121.8(7) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 114.7(6) . . ?
C15 C16 C16 122.6(4) . 4_755 ?
C17 C16 C16 122.5(4) . 4_755 ?
C18 C17 C16 121.1(7) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
N6 C18 C17 122.0(7) . . ?
N6 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
H1W1 O1W H1W2 107.0 . . ?

_refine_diff_density_max         0.790
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.085



