# 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 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_kru401
_database_code_depnum_ccdc_archive 'CCDC 2250755'
loop_
_audit_author_name
_audit_author_address
'Kuratieva Natalia V.'
;Nikolaev Institute of Inorganic Chemistry
Russia
;
_audit_update_record             
;
2023-07-17 deposited with the CCDC.	2023-07-18 downloaded from the CCDC.
;
_audit_creation_date             2023-07-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H10 Cl2 F N3 O Ru'
_chemical_formula_sum            'C10 H10 Cl2 F N3 O Ru'
_chemical_formula_weight         379.18
_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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
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'
Ru Ru -1.2594 0.8363 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   7.343(3)
_cell_length_b                   14.561(6)
_cell_length_c                   12.347(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.381(11)
_cell_angle_gamma                90
_cell_volume                     1312.0(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1694
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   0.882
_shelx_estimated_absorpt_T_min   0.831
_exptl_absorpt_coefficient_mu    1.604
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.920
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   0.745
_exptl_transmission_factor_min   0.471
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4028
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         27.086
_diffrn_reflns_theta_min         2.798
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 25
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Bruker Nonius X8Apex CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                967
_reflns_number_total             1312
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.920
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1312
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+3.5725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1381
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 Ru1-N1
 1.75 with sigma of 0.01
 O1-N1
 1.15 with sigma of 0.01
3. Others
 Fixed Sof: F1(0.5) O1(0.5) N1(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C1(H1), C2(H2), C3(H3), C6(H6)
;
_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
Ru1 Ru 0.500000 0.61648(4) 0.750000 0.0447(3) Uani 1 2 d DS T P . .
Cl1 Cl 0.7293(2) 0.61569(10) 0.90099(15) 0.0506(4) Uani 1 1 d . . . . .
F1 F 0.676(3) 0.6144(14) 0.6571(16) 0.041(6) Uani 0.5 1 d . . P A 2
N3 N 0.500000 0.4729(5) 0.750000 0.0412(17) Uani 1 2 d S T P A .
N2 N 0.500000 0.7595(4) 0.750000 0.0424(18) Uani 1 2 d S T P A .
C4 C 0.5364(8) 0.4258(5) 0.6606(5) 0.0428(14) Uani 1 1 d . . . . .
H4 H 0.560744 0.458593 0.597303 0.051 Uiso 1 1 calc R U . A .
C5 C 0.5389(8) 0.3314(4) 0.6593(7) 0.0549(18) Uani 1 1 d . . . . .
H5 H 0.567378 0.299689 0.596076 0.066 Uiso 1 1 calc R U . . .
C1 C 0.4735(8) 0.8075(5) 0.8408(6) 0.0507(17) Uani 1 1 d . . . . .
H1 H 0.455223 0.774784 0.905214 0.061 Uiso 1 1 calc R U . A .
C2 C 0.4721(9) 0.9021(5) 0.8432(7) 0.061(2) Uani 1 1 d . . . . .
H2 H 0.452246 0.934105 0.907947 0.073 Uiso 1 1 calc R U . . .
C3 C 0.500000 0.9493(7) 0.750000 0.067(3) Uani 1 2 d S T P . .
H3 H 0.499998 1.014582 0.749999 0.081 Uiso 1 2 calc R U P . .
C6 C 0.500000 0.2827(6) 0.750000 0.066(3) Uani 1 2 d S T P . .
H6 H 0.499997 0.217457 0.749999 0.079 Uiso 1 2 calc R U P . .
O1 O 0.7802(14) 0.6199(7) 0.5945(10) 0.071(3) Uani 0.5 1 d D . P A 1
N1 N 0.675(4) 0.621(2) 0.661(3) 0.061(12) Uani 0.5 1 d D . P A 1

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
Ru1 0.0371(4) 0.0292(4) 0.0650(6) 0.000 -0.0065(3) 0.000
Cl1 0.0431(8) 0.0441(8) 0.0617(11) 0.0004(7) -0.0062(8) 0.0007(6)
F1 0.039(11) 0.043(9) 0.043(10) -0.013(7) 0.019(7) 0.011(7)
N3 0.030(3) 0.039(4) 0.054(5) 0.000 0.003(3) 0.000
N2 0.030(3) 0.030(4) 0.066(5) 0.000 0.004(3) 0.000
C4 0.040(3) 0.051(4) 0.038(4) 0.004(3) 0.006(3) 0.000(3)
C5 0.044(4) 0.045(4) 0.075(5) -0.019(4) 0.006(3) 0.001(3)
C1 0.039(3) 0.044(4) 0.069(5) 0.001(3) 0.003(3) 0.008(3)
C2 0.049(4) 0.056(5) 0.077(6) -0.024(4) -0.002(4) 0.007(3)
C3 0.053(6) 0.041(6) 0.106(11) 0.000 0.004(6) 0.000
C6 0.048(6) 0.030(5) 0.121(11) 0.000 0.011(6) 0.000
O1 0.051(6) 0.070(7) 0.097(9) -0.003(6) 0.033(6) -0.003(5)
N1 0.040(18) 0.035(12) 0.10(3) 0.027(13) -0.009(14) -0.014(11)

_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
Ru1 Cl1 2.3689(18) . ?
Ru1 Cl1 2.3690(18) 2_656 ?
Ru1 F1 1.819(9) 2_656 ?
Ru1 F1 1.819(9) . ?
Ru1 N3 2.091(7) . ?
Ru1 N2 2.083(7) . ?
Ru1 N1 1.781(9) 2_656 ?
Ru1 N1 1.781(9) . ?
N3 C4 1.351(7) . ?
N3 C4 1.351(7) 2_656 ?
N2 C1 1.353(8) 2_656 ?
N2 C1 1.353(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(9) . ?
C1 H1 0.9500 . ?
C1 C2 1.378(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(10) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
O1 N1 1.190(9) . ?

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
Cl1 Ru1 Cl1 179.44(8) . 2_656 ?
F1 Ru1 Cl1 90.3(8) . . ?
F1 Ru1 Cl1 89.7(8) 2_656 . ?
F1 Ru1 N3 89.0(6) 2_656 . ?
F1 Ru1 N3 89.0(6) . . ?
F1 Ru1 N2 91.0(6) . . ?
F1 Ru1 N2 91.0(6) 2_656 . ?
N3 Ru1 Cl1 89.72(4) . 2_656 ?
N3 Ru1 Cl1 89.72(4) . . ?
N2 Ru1 Cl1 90.28(4) . 2_656 ?
N2 Ru1 Cl1 90.28(4) . . ?
N2 Ru1 N3 180.0 . . ?
N1 Ru1 Cl1 89.3(13) 2_656 2_656 ?
N1 Ru1 Cl1 90.7(13) 2_656 . ?
N1 Ru1 Cl1 90.7(13) . 2_656 ?
N1 Ru1 Cl1 89.3(13) . . ?
N1 Ru1 F1 3.1(16) 2_656 2_656 ?
N1 Ru1 F1 178.6(15) . 2_656 ?
N1 Ru1 N3 92.0(10) . . ?
N1 Ru1 N3 92.0(11) 2_656 . ?
N1 Ru1 N2 88.0(10) . . ?
N1 Ru1 N2 88.0(11) 2_656 . ?
N1 Ru1 N1 176(2) 2_656 . ?
C4 N3 Ru1 120.5(4) . . ?
C4 N3 Ru1 120.5(4) 2_656 . ?
C4 N3 C4 119.0(7) 2_656 . ?
C1 N2 Ru1 121.1(4) . . ?
C1 N2 Ru1 121.1(4) 2_656 . ?
C1 N2 C1 117.8(8) 2_656 . ?
N3 C4 H4 119.3 . . ?
N3 C4 C5 121.4(6) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.9(7) . . ?
C6 C5 H5 120.0 . . ?
N2 C1 H1 118.8 . . ?
N2 C1 C2 122.5(7) . . ?
C2 C1 H1 118.8 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(8) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C2 120.0(10) 2_656 . ?
C2 C3 H3 120.0 . . ?
C2 C3 H3 120.0 2_656 . ?
C5 C6 C5 118.2(9) . 2_656 ?
C5 C6 H6 120.9 2_656 . ?
C5 C6 H6 120.9 . . ?
O1 N1 Ru1 174(3) . . ?

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
Ru1 N3 C4 C5 179.3(4) . . . . ?
Ru1 N2 C1 C2 -179.8(5) . . . . ?
N3 C4 C5 C6 1.3(8) . . . . ?
N2 C1 C2 C3 -0.5(9) . . . . ?
C4 N3 C4 C5 -0.7(4) 2_656 . . . ?
C4 C5 C6 C5 -0.7(4) . . . 2_656 ?
C1 N2 C1 C2 0.2(5) 2_656 . . . ?
C1 C2 C3 C2 0.2(4) . . . 2_656 ?

_shelx_res_file                  
;
TITL kru401_a.res in C2/c
    kru401.res
    created by SHELXL-2018/3 at 11:43:17 on 12-Jul-2023
REM Old TITL kru401 in C2/c
REM SHELXT solution in C2/c
REM R1 0.168, Rweak 0.007, Alpha 0.039, Orientation as input
REM Formula found by SHELXT: N10 O2 F4 Cl2 Ru
CELL 0.71073 7.3426 14.5611 12.3474 90 96.381 90
ZERR 4 0.0031 0.0058 0.0046 0 0.011 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H Cl F N O Ru
UNIT 40 40 8 4 12 4 4
DFIX 1.75 0.01 Ru1 N1
DFIX 1.15 0.01 O1 N1

L.S. 100
PLAN  20
SIZE 0.08 0.12 0.12
TEMP -123(2)
CONF
GRID
BOND $H
MORE -1
fmap 2
acta 50.5
MERG 2
REM <olex2.extras>
REM <HklSrc "%.\\kru401.hkl">
REM </olex2.extras>

WGHT    0.055600    3.572500
FVAR       0.29107
RU1   7    0.500000    0.616479    0.750000    10.50000    0.03712    0.02921 =
         0.06500    0.00000   -0.00654    0.00000
CL1   3    0.729253    0.615687    0.900992    11.00000    0.04310    0.04415 =
         0.06171    0.00041   -0.00616    0.00069
PART 2
F1    4    0.675619    0.614381    0.657121    10.50000    0.03913    0.04259 =
         0.04331   -0.01294    0.01869    0.01069
PART 0
N3    5    0.500000    0.472865    0.750000    10.50000    0.02959    0.03927 =
         0.05421    0.00000    0.00282    0.00000
N2    5    0.500000    0.759540    0.750000    10.50000    0.03036    0.03041 =
         0.06613    0.00000    0.00367    0.00000
C4    1    0.536383    0.425769    0.660609    11.00000    0.04035    0.05061 =
         0.03785    0.00406    0.00562   -0.00002
AFIX  43
H4    2    0.560744    0.458593    0.597303    11.00000   -1.20000
AFIX   0
C5    1    0.538910    0.331412    0.659287    11.00000    0.04414    0.04509 =
         0.07522   -0.01873    0.00613    0.00094
AFIX  43
H5    2    0.567378    0.299689    0.596076    11.00000   -1.20000
AFIX   0
C1    1    0.473519    0.807534    0.840764    11.00000    0.03950    0.04360 =
         0.06853    0.00066    0.00337    0.00767
AFIX  43
H1    2    0.455223    0.774784    0.905214    11.00000   -1.20000
AFIX   0
C2    1    0.472093    0.902147    0.843215    11.00000    0.04852    0.05559 =
         0.07748   -0.02364   -0.00230    0.00736
AFIX  43
H2    2    0.452246    0.934105    0.907947    11.00000   -1.20000
AFIX   0
C3    1    0.500000    0.949339    0.750000    10.50000    0.05308    0.04114 =
         0.10610    0.00000    0.00369    0.00000
AFIX  43
H3    2    0.499998    1.014582    0.749999    10.50000   -1.20000
AFIX   0
C6    1    0.500000    0.282699    0.750000    10.50000    0.04764    0.02960 =
         0.12125    0.00000    0.01133    0.00000
AFIX  43
H6    2    0.499997    0.217457    0.749999    10.50000   -1.20000
AFIX   0
PART 1
O1    6    0.780212    0.619914    0.594453    10.50000    0.05081    0.07011 =
         0.09728   -0.00254    0.03290   -0.00323
N1    5    0.674795    0.620706    0.660979    10.50000    0.03976    0.03470 =
         0.10434    0.02693   -0.00886   -0.01449
HKLF 4




REM  kru401_a.res in C2/c
REM wR2 = 0.1381, GooF = S = 1.108, Restrained GooF = 1.118 for all data
REM R1 = 0.0452 for 967 Fo > 4sig(Fo) and 0.0668 for all 1312 data
REM 98 parameters refined using 2 restraints

END

WGHT      0.0552      3.6332

REM Highest difference peak  0.920,  deepest hole -0.743,  1-sigma level  0.121
Q1    1   0.5000  0.5544  0.7500  10.50000  0.05    0.92
Q2    1   0.5000  0.6812  0.7500  10.50000  0.05    0.72
Q3    1   0.5274  0.6171  0.6898  11.00000  0.05    0.48
Q4    1   0.5000  1.0700  0.7500  10.50000  0.05    0.46
Q5    1   0.6032  0.6700  0.7154  11.00000  0.05    0.44
Q6    1   0.7843  0.6163  0.8404  11.00000  0.05    0.42
Q7    1   0.7829  0.6912  0.4880  11.00000  0.05    0.42
Q8    1   0.4428  0.7062  0.8326  11.00000  0.05    0.42
Q9    1   0.6319  0.6239  0.9576  11.00000  0.05    0.41
Q10   1   0.5074  0.3144  0.5738  11.00000  0.05    0.37
Q11   1   0.8081  0.6136  0.5758  11.00000  0.05    0.37
Q12   1   0.6018  0.5569  0.7068  11.00000  0.05    0.36
Q13   1   0.5547  0.9791  0.7289  11.00000  0.05    0.35
Q14   1   0.7370  0.5603  0.9018  11.00000  0.05    0.35
Q15   1   0.4947  0.4465  0.7021  11.00000  0.05    0.34
Q16   1   0.4403  0.4688  0.7760  11.00000  0.05    0.34
Q17   1   0.5550  0.7759  0.7188  11.00000  0.05    0.34
Q18   1   0.7167  0.6881  0.6982  11.00000  0.05    0.33
Q19   1   0.4985  0.4309  0.7204  11.00000  0.05    0.33
Q20   1   0.3154  0.8771  0.9372  11.00000  0.05    0.33
;
_shelx_res_checksum              2476
_olex2_submission_special_instructions 'No special instructions were received'
