# Supplementary Information (SI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_sq
_database_code_depnum_ccdc_archive 'CCDC 2369828'
loop_
_audit_author_name
_audit_author_address
'Mingyan Wu'
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2024-07-11 deposited with the CCDC.	2024-08-27 downloaded from the CCDC.
;
_audit_creation_date             2024-06-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H6 F N Ni0.5 O2'
_chemical_formula_sum            'C12 H7 F N Ni0.50 O2'
_chemical_formula_weight         245.54
_chemical_melting_point          ?
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'
F F 0.0727 0.0534 '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      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'x, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x, y-1/2, z-1/2'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.2804(4)
_cell_length_b                   12.1294(3)
_cell_length_c                   15.2030(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3186.56(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7616
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.3770
_cell_measurement_theta_min      3.6350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.191
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.024
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11649
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.419
_diffrn_reflns_theta_min         4.664
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2895
_reflns_number_total             3212
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.948
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         3212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1119P)²+5.1165P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1899
_refine_ls_wR_factor_ref         0.1940
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: F1(0.5) F2(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.7500 1.0000 0.81060(4) 0.0300(2) Uani 1 2 d S T P . .
F1 F 0.5043(6) 0.6209(7) 0.6581(5) 0.154(4) Uani 0.5 1 d . . P . .
F2 F 0.4715(5) 0.9260(4) 0.4886(5) 0.138(4) Uani 0.5 1 d . . P . .
O1 O 0.33379(12) 0.48989(15) 0.41389(14) 0.0380(5) Uani 1 1 d . . . . .
O2 O 0.31242(10) 0.64164(15) 0.33883(12) 0.0349(4) Uani 1 1 d . . . . .
N1 N 0.67457(12) 0.93718(19) 0.72050(15) 0.0340(5) Uani 1 1 d . . . . .
C1 C 0.34668(15) 0.5908(2) 0.40031(18) 0.0338(6) Uani 1 1 d . . . . .
C2 C 0.40296(16) 0.6516(2) 0.45701(18) 0.0365(6) Uani 1 1 d . . . . .
C3 C 0.4351(3) 0.6039(4) 0.5284(3) 0.0900(18) Uani 1 1 d . . . . .
H3 H 0.4204 0.5312 0.5446 0.108 Uiso 1 1 calc R U . . .
C4 C 0.4893(3) 0.6602(4) 0.5783(3) 0.0919(18) Uani 1 1 d . . . . .
C5 C 0.51042(17) 0.7646(2) 0.5613(2) 0.0414(6) Uani 1 1 d . . . . .
C6 C 0.4747(4) 0.8131(4) 0.4904(4) 0.112(2) Uani 1 1 d . . . . .
C7 C 0.4217(4) 0.7573(4) 0.4386(3) 0.103(2) Uani 1 1 d . . . . .
H7 H 0.3984 0.7934 0.3899 0.124 Uiso 1 1 calc R U . . .
C8 C 0.56747(16) 0.8251(2) 0.61554(19) 0.0395(6) Uani 1 1 d . . . . .
C9 C 0.64273(17) 0.7866(3) 0.6253(2) 0.0450(7) Uani 1 1 d . . . . .
H9 H 0.6588 0.7211 0.5964 0.054 Uiso 1 1 calc R U . . .
C10 C 0.69370(17) 0.8444(3) 0.67724(19) 0.0405(7) Uani 1 1 d . . . . .
H10 H 0.7451 0.8174 0.6829 0.049 Uiso 1 1 calc R U . . .
C11 C 0.60215(18) 0.9739(3) 0.7107(2) 0.0456(7) Uani 1 1 d . . . . .
H11 H 0.5876 1.0395 0.7405 0.055 Uiso 1 1 calc R U . . .
C12 C 0.54754(18) 0.9217(3) 0.6596(2) 0.0504(8) Uani 1 1 d . . . . .
H12 H 0.4968 0.9513 0.6544 0.061 Uiso 1 1 calc R 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 O1 2.140(2) 7_666 ?
Ni1 O1 2.140(2) 8_676 ?
Ni1 O2 2.0734(19) 7_666 ?
Ni1 O2 2.0734(19) 8_676 ?
Ni1 N1 2.039(2) 2_675 ?
Ni1 N1 2.039(2) . ?
Ni1 C1 2.422(3) 8_676 ?
Ni1 C1 2.422(3) 7_666 ?
F1 C4 1.330(7) . ?
F2 C6 1.371(6) . ?
O1 Ni1 2.140(2) 7_655 ?
O1 C1 1.262(3) . ?
O2 Ni1 2.0735(19) 7_655 ?
O2 C1 1.266(3) . ?
N1 C10 1.345(4) . ?
N1 C11 1.337(4) . ?
C1 Ni1 2.422(3) 7_655 ?
C1 C2 1.494(4) . ?
C2 C3 1.350(5) . ?
C2 C7 1.351(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(5) . ?
C4 C5 1.342(5) . ?
C5 C6 1.374(5) . ?
C5 C8 1.481(4) . ?
C6 C7 1.385(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(4) . ?
C8 C12 1.393(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.375(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.376(4) . ?
C12 H12 0.9500 . ?

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
O1 Ni1 O1 85.56(12) 8_676 7_666 ?
O1 Ni1 C1 91.57(8) 7_666 8_676 ?
O1 Ni1 C1 31.34(8) 8_676 8_676 ?
O1 Ni1 C1 31.34(8) 7_666 7_666 ?
O1 Ni1 C1 91.57(8) 8_676 7_666 ?
O2 Ni1 O1 62.84(7) 8_676 8_676 ?
O2 Ni1 O1 98.78(8) 7_666 8_676 ?
O2 Ni1 O1 98.78(7) 8_676 7_666 ?
O2 Ni1 O1 62.84(7) 7_666 7_666 ?
O2 Ni1 O2 156.11(11) 7_666 8_676 ?
O2 Ni1 C1 31.53(8) 8_676 8_676 ?
O2 Ni1 C1 128.26(9) 7_666 8_676 ?
O2 Ni1 C1 128.26(9) 8_676 7_666 ?
O2 Ni1 C1 31.53(8) 7_666 7_666 ?
N1 Ni1 O1 161.32(8) . 8_676 ?
N1 Ni1 O1 92.24(9) . 7_666 ?
N1 Ni1 O1 92.24(9) 2_675 8_676 ?
N1 Ni1 O1 161.32(8) 2_675 7_666 ?
N1 Ni1 O2 96.67(8) . 7_666 ?
N1 Ni1 O2 99.32(8) . 8_676 ?
N1 Ni1 O2 96.67(8) 2_675 8_676 ?
N1 Ni1 O2 99.32(8) 2_675 7_666 ?
N1 Ni1 N1 95.57(13) . 2_675 ?
N1 Ni1 C1 96.16(9) 2_675 8_676 ?
N1 Ni1 C1 130.50(9) 2_675 7_666 ?
N1 Ni1 C1 96.16(9) . 7_666 ?
N1 Ni1 C1 130.50(9) . 8_676 ?
C1 Ni1 C1 111.46(13) 8_676 7_666 ?
C1 O1 Ni1 86.77(16) . 7_655 ?
C1 O2 Ni1 89.60(16) . 7_655 ?
C10 N1 Ni1 118.96(18) . . ?
C11 N1 Ni1 123.3(2) . . ?
C11 N1 C10 117.0(2) . . ?
O1 C1 Ni1 61.89(14) . 7_655 ?
O1 C1 O2 120.7(2) . . ?
O1 C1 C2 120.0(2) . . ?
O2 C1 Ni1 58.88(13) . 7_655 ?
O2 C1 C2 119.4(2) . . ?
C2 C1 Ni1 176.77(19) . 7_655 ?
C3 C2 C1 121.4(3) . . ?
C7 C2 C1 120.3(3) . . ?
C7 C2 C3 118.3(3) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
F1 C4 C3 117.1(5) . . ?
F1 C4 C5 117.4(5) . . ?
C5 C4 C3 122.9(3) . . ?
C4 C5 C6 115.6(3) . . ?
C4 C5 C8 122.8(3) . . ?
C6 C5 C8 121.6(3) . . ?
F2 C6 C5 117.5(4) . . ?
F2 C6 C7 116.8(5) . . ?
C5 C6 C7 122.2(4) . . ?
C2 C7 C6 120.3(4) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C5 121.1(3) . . ?
C9 C8 C12 117.6(3) . . ?
C12 C8 C5 121.4(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.3 . . ?
N1 C10 C9 123.4(3) . . ?
N1 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
N1 C11 H11 118.2 . . ?
N1 C11 C12 123.5(3) . . ?
C12 C11 H11 118.2 . . ?
C8 C12 H12 120.4 . . ?
C11 C12 C8 119.2(3) . . ?
C11 C12 H12 120.4 . . ?

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 O1 C1 O2 -3.1(2) 7_655 . . . ?
Ni1 O1 C1 C2 177.0(2) 7_655 . . . ?
Ni1 O2 C1 O1 3.2(3) 7_655 . . . ?
Ni1 O2 C1 C2 -176.9(2) 7_655 . . . ?
Ni1 N1 C10 C9 170.0(3) . . . . ?
Ni1 N1 C11 C12 -170.0(3) . . . . ?
F1 C4 C5 C6 -161.3(8) . . . . ?
F1 C4 C5 C8 17.8(10) . . . . ?
F2 C6 C7 C2 -158.0(7) . . . . ?
O1 C1 C2 C3 -6.6(5) . . . . ?
O1 C1 C2 C7 174.7(4) . . . . ?
O2 C1 C2 C3 173.5(4) . . . . ?
O2 C1 C2 C7 -5.2(5) . . . . ?
N1 C11 C12 C8 0.3(6) . . . . ?
C1 C2 C3 C4 177.6(5) . . . . ?
C1 C2 C7 C6 -179.1(5) . . . . ?
C2 C3 C4 F1 164.0(8) . . . . ?
C2 C3 C4 C5 2.7(10) . . . . ?
C3 C2 C7 C6 2.2(9) . . . . ?
C3 C4 C5 C6 -0.1(9) . . . . ?
C3 C4 C5 C8 179.0(5) . . . . ?
C4 C5 C6 F2 156.8(7) . . . . ?
C4 C5 C6 C7 -1.5(10) . . . . ?
C4 C5 C8 C9 59.8(5) . . . . ?
C4 C5 C8 C12 -119.3(5) . . . . ?
C5 C6 C7 C2 0.4(11) . . . . ?
C5 C8 C9 C10 -179.1(3) . . . . ?
C5 C8 C12 C11 178.7(3) . . . . ?
C6 C5 C8 C9 -121.2(5) . . . . ?
C6 C5 C8 C12 59.7(6) . . . . ?
C7 C2 C3 C4 -3.7(9) . . . . ?
C8 C5 C6 F2 -22.3(9) . . . . ?
C8 C5 C6 C7 179.4(6) . . . . ?
C8 C9 C10 N1 0.5(5) . . . . ?
C9 C8 C12 C11 -0.4(5) . . . . ?
C10 N1 C11 C12 0.2(5) . . . . ?
C11 N1 C10 C9 -0.7(5) . . . . ?
C12 C8 C9 C10 0.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
