# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 2131072'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-12-27 deposited with the CCDC.	2022-05-12 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 F4 N2, Cl'
_chemical_formula_sum            'C15 H9 Cl F4 N2'
_chemical_formula_weight         328.69
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     PRO-197
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'
Cl Cl 0.3639 0.7018 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.44484(8)
_cell_length_b                   8.57651(16)
_cell_length_c                   12.8743(2)
_cell_angle_alpha                96.2904(15)
_cell_angle_beta                 100.2456(13)
_cell_angle_gamma                94.1463(12)
_cell_volume                     692.98(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9307
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.3430
_cell_measurement_theta_min      6.9880
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.657
_exptl_absorpt_coefficient_mu    2.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8364
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.572
_diffrn_reflns_theta_min         3.516
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -74.00   0.40    0.50    --  -48.51-126.00-167.00  115
  2  ω    -86.00 -14.00   0.40    0.50    --  -48.51 126.00 -91.00  180
  3  ω   -101.00 -23.00   0.40    0.50    --  -48.51 145.00  76.00  195
  4  ω   -120.00 -60.00   0.40    0.50    --  -48.51-145.00  24.00  150
  5  ω     45.00 107.00   0.40    0.50    --   48.51-145.00  24.00  155
  6  ω     35.00  95.00   0.40    0.50    --   48.51-126.00-167.00  150
  7  ω   -153.00 -61.00   0.40    0.50    --  -90.00-145.00  24.00  230
  8  ω   -161.00 -73.00   0.40    0.50    --  -90.00-126.00-167.00  220
  9  ω   -100.00 -24.00   0.40    0.50    --  -90.00 145.00  76.00  190
 10  ω    -87.00 -19.00   0.40    0.50    --  -90.00 126.00 -91.00  170
 11  ω     81.00 169.00   0.40    0.50    --  111.50 145.00  76.00  220
 12  ω     45.00 125.00   0.40    0.50    --  111.50-145.00  24.00  200
 13  ω     95.00 177.00   0.40    0.50    --  111.50 126.00 -91.00  205
 14  ω     40.00 112.00   0.40    0.50    --  111.50-126.00-167.00  180
 15  ω    -43.00  23.00   0.40    0.50    --  -48.51  38.00 -90.00  165
 16  ω    -26.00  26.00   0.40    0.50    --  -48.51  19.00-150.00  130
 17  ω   -120.00 -28.00   0.40    0.50    --  -48.51 -77.00  90.00  230
 18  ω     27.00 119.00   0.40    0.50    --   48.51  77.00 -60.00  230
 19  ω   -163.00 -79.00   0.40    0.50    --  -90.00 -30.00-120.00  210
 20  ω     40.00 104.00   0.40    0.50    --  111.50 -95.00  30.00  160
 21  ω    101.00 177.00   0.40    0.50    --  111.50  45.00   0.00  190
 22  ω     40.00  70.00   0.40    0.50    --  111.50 -61.00  60.00   75
 23  ω     40.00  70.00   0.40    0.50    --  111.50 -61.00 -90.00   75
 24  ω     40.00 104.00   0.40    0.50    --  111.50 -77.00  30.00  160
 25  ω    101.00 177.00   0.40    0.50    --  111.50  45.00 -90.00  190
 26  ω    101.00 177.00   0.40    0.50    --  111.50  15.00-180.00  190
 27  ω     40.00 104.00   0.40    0.50    --  111.50 -95.00  90.00  160
 28  ω    101.00 177.00   0.40    0.50    --  111.50  15.00  90.00  190
 29  ω    101.00 177.00   0.40    0.50    --  111.50  30.00 120.00  190
 30  ω     40.00 104.00   0.40    0.50    --  111.50 -77.00-120.00  160
 31  ω    101.00 177.00   0.40    0.50    --  111.50  15.00-120.00  190
 32  ω     40.00 104.00   0.40    0.50    --  111.50 -77.00 120.00  160
 33  ω     40.00 110.00   0.40    0.50    --  111.50-125.00 150.00  175
 34  ω     66.00 103.20   0.40    0.50    --  111.50 -77.00 150.00   93
 35  ω     68.80 108.00   0.40    0.50    --  111.50-112.00 -54.04   98
 36  ω    107.00 176.20   0.40    0.50    --  111.50  30.00 -30.00  173
 37  ω     74.00  99.20   0.40    0.50    --  111.50 -77.00 -30.00   63
 38  ω     68.00  95.20   0.40    0.50    --  111.50 -95.00-150.00   68
 39  ω     40.00  76.00   0.40    0.50    --  111.50 -77.00-150.00   90
 40  ω     40.00  78.00   0.40    0.50    --  111.50-125.00  90.00   95
 41  ω     85.00 110.20   0.40    0.50    --  111.50-125.00  60.00   63
 42  ω     40.00  70.00   0.40    0.50    --  111.50 -77.00 -30.00   75
 43  ω     48.00  73.20   0.40    0.50    --  111.50-125.00  60.00   63
 44  ω     82.00 107.20   0.40    0.50    --  111.50-125.00  90.00   63
 45  ω    106.00 135.20   0.40    0.50    --  111.50  15.00 -60.00   73
 46  ω    149.00 176.20   0.40    0.50    --  111.50  15.00 -60.00   68
 47  ω     76.00 106.00   0.40    0.50    --  111.50-125.00-150.00   75
 48  ω     57.00 103.00   0.40    0.50    --  111.50 -77.00 -60.00  115
 49  ω     41.00  68.20   0.40    0.50    --  111.50 -61.00 -30.00   68
 50  ω     40.00  66.00   0.40    0.50    --  111.50 -95.00-150.00   65
 51  ω    101.00 177.00   0.40    0.50    --  111.50  45.00-180.00  190
 52  ω     44.00  83.20   0.40    0.50    --  111.50 -77.00 -90.00   98
 53  ω     58.00  84.00   0.40    0.50    --  111.50 -95.00   0.00   65
 54  ω     47.00  77.00   0.40    0.50    --  111.50 -95.00 120.00   75
 55  ω     45.00  71.00   0.40    0.50    --  111.50-109.00 -90.27   65
 56  ω     80.80 108.00   0.40    0.50    --  111.50-109.00 -90.27   68
 57  ω     85.00 110.20   0.40    0.50    --  111.50-125.00-180.00   63
 58  ω     58.00 107.20   0.40    0.50    --  111.50-125.00 120.00  123
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0008262000
_diffrn_orient_matrix_UB_12      -0.1242816000
_diffrn_orient_matrix_UB_13      0.0778359000
_diffrn_orient_matrix_UB_21      0.0784829000
_diffrn_orient_matrix_UB_22      0.1297825000
_diffrn_orient_matrix_UB_23      0.0943239000
_diffrn_orient_matrix_UB_31      -0.2310197000
_diffrn_orient_matrix_UB_32      0.0256553000
_diffrn_orient_matrix_UB_33      0.0080649000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7572
_reflns_number_total             8364
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    
'SHELXT (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         8364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.094
_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)+(0.1014P)²+0.0833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1427
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5582(14)
 0.4418(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C8(H8), C9(H9), C11(H11), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.75751(7) 0.65727(5) 0.44551(3) 0.02520(18) Uani 1 1 d . . . . .
F1 F 0.2675(2) 0.60749(15) 0.85300(10) 0.0353(3) Uani 1 1 d . . . . .
F2 F 0.2995(2) 0.89428(16) 0.96592(9) 0.0383(3) Uani 1 1 d . . . . .
F3 F 0.2194(2) 0.18748(13) 0.22007(10) 0.0340(3) Uani 1 1 d . . . . .
F4 F 0.2404(3) 0.27399(17) 0.02744(10) 0.0465(4) Uani 1 1 d . . . . .
N1 N 0.2632(2) 0.83666(18) 0.53035(12) 0.0214(3) Uani 1 1 d . . . . .
N2 N 0.2405(3) 0.72792(18) 0.36802(13) 0.0218(3) Uani 1 1 d . . . . .
C1 C 0.2658(3) 0.7003(2) 0.46902(14) 0.0224(4) Uani 1 1 d . . . . .
H1 H 0.282915 0.600619 0.493536 0.027 Uiso 1 1 calc R U . . .
C2 C 0.2194(3) 0.8872(2) 0.36440(15) 0.0244(4) Uani 1 1 d . . . . .
H2 H 0.198908 0.938789 0.302235 0.029 Uiso 1 1 calc R U . . .
C3 C 0.2332(3) 0.9550(2) 0.46481(15) 0.0246(4) Uani 1 1 d . . . . .
H3 H 0.224200 1.063322 0.486912 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2756(3) 0.8533(2) 0.64298(15) 0.0224(4) Uani 1 1 d . . . . .
C5 C 0.2658(3) 0.7181(2) 0.69374(15) 0.0248(4) Uani 1 1 d . . . . .
H5 H 0.251702 0.616091 0.654626 0.030 Uiso 1 1 calc R U . . .
C6 C 0.2772(3) 0.7369(2) 0.80206(16) 0.0271(4) Uani 1 1 d . . . . .
C7 C 0.2944(3) 0.8843(3) 0.86032(15) 0.0297(4) Uani 1 1 d . . . . .
C8 C 0.3042(3) 1.0180(2) 0.81009(16) 0.0294(4) Uani 1 1 d . . . . .
H8 H 0.317293 1.119298 0.849996 0.035 Uiso 1 1 calc R U . . .
C9 C 0.2946(3) 1.0034(2) 0.70025(15) 0.0260(4) Uani 1 1 d . . . . .
H9 H 0.301039 1.094558 0.664778 0.031 Uiso 1 1 calc R U . . .
C10 C 0.2381(3) 0.6107(2) 0.27906(15) 0.0242(4) Uani 1 1 d . . . . .
C11 C 0.2283(3) 0.4523(2) 0.29478(15) 0.0247(4) Uani 1 1 d . . . . .
H11 H 0.221165 0.421038 0.362715 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2294(3) 0.3424(2) 0.20819(16) 0.0274(4) Uani 1 1 d . . . . .
C13 C 0.2384(4) 0.3869(3) 0.10911(17) 0.0340(5) Uani 1 1 d . . . . .
C14 C 0.2483(4) 0.5427(3) 0.09451(17) 0.0385(5) Uani 1 1 d . . . . .
H14 H 0.255370 0.572828 0.026295 0.046 Uiso 1 1 calc R U . . .
C15 C 0.2480(4) 0.6567(3) 0.18016(16) 0.0324(5) Uani 1 1 d . . . . .
H15 H 0.254629 0.765166 0.170828 0.039 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
F1 C6 1.353(2) . ?
F2 C7 1.347(2) . ?
F3 C12 1.352(2) . ?
F4 C13 1.352(2) . ?
N1 C1 1.341(2) . ?
N1 C3 1.392(2) . ?
N1 C4 1.429(2) . ?
N2 C1 1.331(2) . ?
N2 C2 1.387(2) . ?
N2 C10 1.436(2) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.343(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(3) . ?
C4 C9 1.397(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.374(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.380(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.396(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(3) . ?
C10 C15 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(3) . ?
C12 C13 1.381(3) . ?
C13 C14 1.368(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(3) . ?
C15 H15 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
C1 N1 C3 108.34(15) . . ?
C1 N1 C4 125.01(15) . . ?
C3 N1 C4 126.53(16) . . ?
C1 N2 C2 108.57(15) . . ?
C1 N2 C10 124.84(16) . . ?
C2 N2 C10 126.59(16) . . ?
N1 C1 H1 125.7 . . ?
N2 C1 N1 108.54(16) . . ?
N2 C1 H1 125.7 . . ?
N2 C2 H2 126.2 . . ?
C3 C2 N2 107.53(16) . . ?
C3 C2 H2 126.2 . . ?
N1 C3 H3 126.5 . . ?
C2 C3 N1 107.02(16) . . ?
C2 C3 H3 126.5 . . ?
C5 C4 N1 118.97(16) . . ?
C5 C4 C9 121.10(18) . . ?
C9 C4 N1 119.93(17) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 C4 117.96(17) . . ?
C6 C5 H5 121.0 . . ?
F1 C6 C5 119.03(18) . . ?
F1 C6 C7 119.00(18) . . ?
C5 C6 C7 121.96(18) . . ?
F2 C7 C6 118.92(18) . . ?
F2 C7 C8 121.03(18) . . ?
C8 C7 C6 120.05(18) . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.56(18) . . ?
C9 C8 H8 120.2 . . ?
C4 C9 H9 120.3 . . ?
C8 C9 C4 119.36(18) . . ?
C8 C9 H9 120.3 . . ?
C11 C10 N2 118.94(17) . . ?
C15 C10 N2 119.70(18) . . ?
C15 C10 C11 121.36(18) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 C10 117.65(18) . . ?
C12 C11 H11 121.2 . . ?
F3 C12 C11 119.46(18) . . ?
F3 C12 C13 119.06(17) . . ?
C11 C12 C13 121.48(19) . . ?
F4 C13 C12 118.8(2) . . ?
F4 C13 C14 120.77(19) . . ?
C14 C13 C12 120.45(18) . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.62(19) . . ?
C15 C14 H14 120.2 . . ?
C10 C15 C14 119.5(2) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?

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
F1 C6 C7 F2 -0.5(3) . . . . ?
F1 C6 C7 C8 -179.88(19) . . . . ?
F2 C7 C8 C9 -178.82(19) . . . . ?
F3 C12 C13 F4 -1.0(3) . . . . ?
F3 C12 C13 C14 179.9(2) . . . . ?
F4 C13 C14 C15 -179.4(2) . . . . ?
N1 C4 C5 C6 -179.77(17) . . . . ?
N1 C4 C9 C8 179.29(18) . . . . ?
N2 C2 C3 N1 0.1(2) . . . . ?
N2 C10 C11 C12 -179.05(18) . . . . ?
N2 C10 C15 C14 179.2(2) . . . . ?
C1 N1 C3 C2 -0.3(2) . . . . ?
C1 N1 C4 C5 -7.7(3) . . . . ?
C1 N1 C4 C9 173.03(18) . . . . ?
C1 N2 C2 C3 0.2(2) . . . . ?
C1 N2 C10 C11 10.5(3) . . . . ?
C1 N2 C10 C15 -168.66(19) . . . . ?
C2 N2 C1 N1 -0.4(2) . . . . ?
C2 N2 C10 C11 -170.11(19) . . . . ?
C2 N2 C10 C15 10.7(3) . . . . ?
C3 N1 C1 N2 0.5(2) . . . . ?
C3 N1 C4 C5 167.95(18) . . . . ?
C3 N1 C4 C9 -11.3(3) . . . . ?
C4 N1 C1 N2 176.81(16) . . . . ?
C4 N1 C3 C2 -176.59(17) . . . . ?
C4 C5 C6 F1 179.83(18) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C5 C4 C9 C8 0.0(3) . . . . ?
C5 C6 C7 F2 178.32(18) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C4 -0.1(3) . . . . ?
C9 C4 C5 C6 -0.5(3) . . . . ?
C10 N2 C1 N1 179.02(16) . . . . ?
C10 N2 C2 C3 -179.22(17) . . . . ?
C10 C11 C12 F3 -179.78(17) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C11 C10 C15 C14 0.0(3) . . . . ?
C11 C12 C13 F4 179.6(2) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C10 0.1(4) . . . . ?
C15 C10 C11 C12 0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.428
_oxdiff_exptl_absorpt_empirical_full_min 0.608
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5582(14) 13822 1235 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4418(14) 13685 1235 nmt 1.0003 0.0001 0.0000 -0.1904 -1.0000 0.0026 -0.7104
-0.0055 -1.0003

_twin_special_details            
;
Component 2 rotated by -179.7867° 
around [0.94 -0.09 -0.33] (reciprocal) or [1.00 0.00 0.00] (direct)
;
####################################################################### 
# 
# 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_4a_2
_database_code_depnum_ccdc_archive 'CCDC 2131074'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-12-27 deposited with the CCDC.	2022-05-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT601_4a_2                
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS of .         38 Ang**3
RESPONSE: According to the analysis of the residual electron density,
 the voids contain no solvent molecules.
;
# start Validation Reply Form
_vrf_PLAT941_4a_2                
;
PROBLEM: Average HKL Measurement Multiplicity ...........        2.5 Low
RESPONSE: Friedel equivalents were merged during the integration procedure.
The real redundancy is twice as higher.
;
# end Validation Reply Form
_audit_creation_date             2021-09-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 Cl2 F2 N3 Pd'
_chemical_formula_sum            'C20 H15 Cl2 F2 N3 Pd'
_chemical_formula_weight         512.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Pd Cl2 F2 N3 C20 H20'
_chemical_oxdiff_usercomment     Pro_4a_O-F
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'
Pd Pd -0.9988 1.0072 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4450(2)
_cell_length_b                   13.5214(3)
_cell_length_c                   31.7529(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.913(2)
_cell_angle_gamma                90
_cell_volume                     4045.70(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    23231
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      35.3390
_cell_measurement_theta_min      2.1380
_shelx_estimated_absorpt_T_max   0.839
_shelx_estimated_absorpt_T_min   0.760
_exptl_absorpt_coefficient_mu    1.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.106a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            41826
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.000
_diffrn_reflns_theta_min         2.161
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00 -13.00   0.30    3.50    --  -26.44 -38.00 136.00  100
  2  ω    -52.00  21.20   0.30    3.50    --   26.75 -38.00 136.00  244
  3  ω     -5.00 104.20   0.30    3.50    --   26.75  38.00 -68.00  364
  4  ω   -102.00 -69.00   0.30    3.50    --  -26.44-178.00-120.00  110
  5  ω   -104.00 -68.00   0.30    3.50    --  -26.44-178.00-150.00  120
  6  ω     42.00  97.20   0.30    3.50    --   26.75 178.00 120.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0660073000
_diffrn_orient_matrix_UB_12      0.0205682000
_diffrn_orient_matrix_UB_13      0.0047264000
_diffrn_orient_matrix_UB_21      0.0295921000
_diffrn_orient_matrix_UB_22      0.0142877000
_diffrn_orient_matrix_UB_23      0.0202258000
_diffrn_orient_matrix_UB_31      0.0205129000
_diffrn_orient_matrix_UB_32      0.0461263000
_diffrn_orient_matrix_UB_33      -0.0084053000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                13781
_reflns_number_total             16449
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.07
_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       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.875
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     625
_refine_ls_number_reflns         16449
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0317P)²+0.9405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0720
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Pd1A Pd 0.23368(2) 0.45373(2) 0.40318(2) 0.01463(3) Uani 1 1 d . . . . .
Cl1A Cl 0.00573(4) 0.42585(3) 0.37418(2) 0.02052(7) Uani 1 1 d . . . . .
Cl2A Cl 0.46630(4) 0.46627(3) 0.43001(2) 0.01938(7) Uani 1 1 d . . . . .
F1A F 0.08126(13) 0.13999(8) 0.34030(3) 0.0327(2) Uani 1 1 d . . . . .
F2A F 0.60142(10) 0.47243(7) 0.29593(3) 0.02466(19) Uani 1 1 d . . . . .
N1A N 0.30117(14) 0.26786(9) 0.35855(4) 0.0165(2) Uani 1 1 d . . . . .
C1A C 0.29929(16) 0.36781(10) 0.35917(4) 0.0160(2) Uani 1 1 d . . . . .
N2A N 0.35159(14) 0.39543(9) 0.32227(4) 0.0171(2) Uani 1 1 d . . . . .
C2A C 0.38598(17) 0.31275(11) 0.29868(5) 0.0197(3) Uani 1 1 d . . . . .
H2A H 0.421(2) 0.3200(14) 0.2724(7) 0.022(5) Uiso 1 1 d . . . . .
C3A C 0.35450(17) 0.23300(11) 0.32150(5) 0.0193(3) Uani 1 1 d . . . . .
H3A H 0.361(2) 0.1638(14) 0.3163(6) 0.018(5) Uiso 1 1 d . . . . .
C4A C 0.24732(16) 0.20763(11) 0.39087(5) 0.0175(3) Uani 1 1 d . . . . .
C5A C 0.13572(18) 0.14403(12) 0.38085(5) 0.0229(3) Uani 1 1 d . . . . .
C6A C 0.0777(2) 0.08583(13) 0.41091(6) 0.0294(4) Uani 1 1 d . . . . .
H6A H 0.002(3) 0.0429(16) 0.4020(8) 0.038(6) Uiso 1 1 d . . . . .
C7A C 0.1341(2) 0.09168(13) 0.45227(6) 0.0286(4) Uani 1 1 d . . . . .
H7A H 0.096(2) 0.0532(14) 0.4721(7) 0.028(6) Uiso 1 1 d . . . . .
C8A C 0.2457(2) 0.15513(13) 0.46321(5) 0.0275(3) Uani 1 1 d . . . . .
H8A H 0.280(2) 0.1578(16) 0.4900(7) 0.036(6) Uiso 1 1 d . . . . .
C9A C 0.30213(19) 0.21367(12) 0.43248(5) 0.0224(3) Uani 1 1 d . . . . .
H9A H 0.375(2) 0.2619(15) 0.4388(7) 0.028(5) Uiso 1 1 d . . . . .
C10A C 0.36153(16) 0.49607(11) 0.30889(4) 0.0169(3) Uani 1 1 d . . . . .
C11A C 0.48757(16) 0.53314(11) 0.29593(5) 0.0182(3) Uani 1 1 d . . . . .
C12A C 0.50097(18) 0.63038(12) 0.28337(5) 0.0214(3) Uani 1 1 d . . . . .
H12A H 0.588(2) 0.6525(15) 0.2745(7) 0.032(6) Uiso 1 1 d . . . . .
C13A C 0.38508(18) 0.69243(12) 0.28468(5) 0.0227(3) Uani 1 1 d . . . . .
H13A H 0.394(2) 0.7589(15) 0.2770(7) 0.027(5) Uiso 1 1 d . . . . .
C14A C 0.25719(19) 0.65666(13) 0.29743(5) 0.0246(3) Uani 1 1 d . . . . .
H14A H 0.180(2) 0.6960(16) 0.2975(7) 0.032(6) Uiso 1 1 d . . . . .
C15A C 0.24505(18) 0.55854(12) 0.30912(5) 0.0221(3) Uani 1 1 d . . . . .
H15A H 0.167(2) 0.5340(14) 0.3165(7) 0.022(5) Uiso 1 1 d . . . . .
N3A N 0.16106(14) 0.54635(9) 0.44991(4) 0.0176(2) Uani 1 1 d . . . . .
C16A C 0.20585(18) 0.53341(11) 0.49059(5) 0.0199(3) Uani 1 1 d . . . . .
H16A H 0.278(2) 0.4841(13) 0.4954(6) 0.016(4) Uiso 1 1 d . . . . .
C17A C 0.14897(19) 0.58541(12) 0.52317(5) 0.0237(3) Uani 1 1 d . . . . .
H17A H 0.183(2) 0.5704(14) 0.5505(7) 0.025(5) Uiso 1 1 d . . . . .
C18A C 0.04449(19) 0.65528(13) 0.51330(6) 0.0261(3) Uani 1 1 d . . . . .
H18A H 0.002(2) 0.6897(15) 0.5330(7) 0.029(5) Uiso 1 1 d . . . . .
C19A C 0.00144(18) 0.67147(12) 0.47136(6) 0.0246(3) Uani 1 1 d . . . . .
H19A H -0.065(2) 0.7189(15) 0.4635(7) 0.025(5) Uiso 1 1 d . . . . .
C20A C 0.06097(17) 0.61506(12) 0.44068(5) 0.0211(3) Uani 1 1 d . . . . .
H20A H 0.032(2) 0.6210(13) 0.4147(6) 0.015(4) Uiso 1 1 d . . . . .
Pd1B Pd 0.30704(2) 0.43493(2) 0.13678(2) 0.01750(3) Uani 1 1 d . . . . .
Cl1B Cl 0.19102(5) 0.42096(3) 0.07056(2) 0.02501(8) Uani 1 1 d . . . . .
Cl2B Cl 0.43735(6) 0.43689(3) 0.20074(2) 0.03130(10) Uani 1 1 d . . . . .
F1B F 0.34634(12) 0.16007(8) 0.03608(3) 0.0287(2) Uani 1 1 d . . . . .
F2B F 0.16967(11) 0.17182(8) 0.24241(3) 0.0265(2) Uani 1 1 d . . . . .
N1B N 0.35597(15) 0.22265(9) 0.11835(4) 0.0187(2) Uani 1 1 d . . . . .
C1B C 0.28844(17) 0.29160(11) 0.14019(5) 0.0188(3) Uani 1 1 d . . . . .
N2B N 0.19113(15) 0.24090(9) 0.16121(4) 0.0193(2) Uani 1 1 d . . . . .
C2B C 0.19760(18) 0.13972(11) 0.15190(5) 0.0208(3) Uani 1 1 d . . . . .
H2B H 0.137(2) 0.0938(14) 0.1651(6) 0.020(5) Uiso 1 1 d . . . . .
C3B C 0.30011(18) 0.12870(11) 0.12499(5) 0.0210(3) Uani 1 1 d . . . . .
H3B H 0.335(2) 0.0745(14) 0.1131(6) 0.018(5) Uiso 1 1 d . . . . .
C4B C 0.46790(17) 0.24537(11) 0.09203(5) 0.0193(3) Uani 1 1 d . . . . .
C5B C 0.46076(18) 0.21266(12) 0.05077(5) 0.0224(3) Uani 1 1 d . . . . .
C6B C 0.5651(2) 0.23386(14) 0.02389(5) 0.0300(4) Uani 1 1 d . . . . .
H6B H 0.557(2) 0.2075(15) -0.0044(7) 0.034(6) Uiso 1 1 d . . . . .
C7B C 0.6773(2) 0.29297(15) 0.03862(6) 0.0341(4) Uani 1 1 d . . . . .
H7B H 0.747(3) 0.3091(17) 0.0215(8) 0.045(7) Uiso 1 1 d . . . . .
C8B C 0.6867(2) 0.32728(15) 0.07989(6) 0.0311(4) Uani 1 1 d . . . . .
H8B H 0.760(3) 0.3596(19) 0.0893(8) 0.047(7) Uiso 1 1 d . . . . .
C9B C 0.58225(19) 0.30291(13) 0.10702(5) 0.0249(3) Uani 1 1 d . . . . .
H9B H 0.588(2) 0.3231(14) 0.1348(6) 0.022(5) Uiso 1 1 d . . . . .
C10B C 0.09888(18) 0.28666(12) 0.18929(5) 0.0215(3) Uani 1 1 d . . . . .
C11B C 0.09511(17) 0.25393(12) 0.23059(5) 0.0220(3) Uani 1 1 d . . . . .
C12B C 0.0182(2) 0.30218(14) 0.25997(6) 0.0279(3) Uani 1 1 d . . . . .
H12B H 0.020(3) 0.2816(16) 0.2877(8) 0.041(6) Uiso 1 1 d . . . . .
C13B C -0.0614(2) 0.38381(14) 0.24690(7) 0.0348(4) Uani 1 1 d . . . . .
H13B H -0.113(3) 0.4178(18) 0.2663(8) 0.046(7) Uiso 1 1 d . . . . .
C14B C -0.0644(2) 0.41552(15) 0.20541(7) 0.0384(5) Uani 1 1 d . . . . .
H14B H -0.119(3) 0.4672(17) 0.1971(8) 0.040(7) Uiso 1 1 d . . . . .
C15B C 0.0158(2) 0.36732(14) 0.17644(6) 0.0315(4) Uani 1 1 d . . . . .
H15B H 0.007(2) 0.3823(15) 0.1467(7) 0.031(6) Uiso 1 1 d . . . . .
N3B N 0.31047(15) 0.58892(10) 0.13382(4) 0.0198(2) Uani 1 1 d . . . . .
C16B C 0.3376(2) 0.63814(12) 0.09859(5) 0.0246(3) Uani 1 1 d . . . . .
H16B H 0.359(2) 0.5972(14) 0.0761(7) 0.023(5) Uiso 1 1 d . . . . .
C17B C 0.3360(2) 0.74042(13) 0.09638(6) 0.0265(3) Uani 1 1 d . . . . .
H17B H 0.354(2) 0.7718(16) 0.0713(7) 0.035(6) Uiso 1 1 d . . . . .
C18B C 0.30328(18) 0.79447(12) 0.13135(6) 0.0240(3) Uani 1 1 d . . . . .
H18B H 0.301(2) 0.8596(17) 0.1302(7) 0.037(6) Uiso 1 1 d . . . . .
C19B C 0.27333(18) 0.74413(12) 0.16780(5) 0.0233(3) Uani 1 1 d . . . . .
H19B H 0.252(2) 0.7767(14) 0.1935(6) 0.023(5) Uiso 1 1 d . . . . .
C20B C 0.27867(18) 0.64174(11) 0.16795(5) 0.0210(3) Uani 1 1 d . . . . .
H20B H 0.258(2) 0.6078(14) 0.1901(6) 0.020(5) Uiso 1 1 d . . . . .


_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
Pd1A Cl1A 2.3140(4) . ?
Pd1A Cl2A 2.3079(4) . ?
Pd1A C1A 1.9507(14) . ?
Pd1A N3A 2.0927(12) . ?
F1A C5A 1.3546(19) . ?
F2A C11A 1.3529(18) . ?
N1A C1A 1.3517(19) . ?
N1A C3A 1.3933(19) . ?
N1A C4A 1.4305(18) . ?
C1A N2A 1.3547(18) . ?
N2A C2A 1.3962(19) . ?
N2A C10A 1.4305(19) . ?
C2A H2A 0.93(2) . ?
C2A C3A 1.344(2) . ?
C3A H3A 0.952(18) . ?
C4A C5A 1.381(2) . ?
C4A C9A 1.388(2) . ?
C5A C6A 1.379(2) . ?
C6A H6A 0.95(2) . ?
C6A C7A 1.385(3) . ?
C7A H7A 0.91(2) . ?
C7A C8A 1.385(3) . ?
C8A H8A 0.89(2) . ?
C8A C9A 1.391(2) . ?
C9A H9A 0.96(2) . ?
C10A C11A 1.380(2) . ?
C10A C15A 1.387(2) . ?
C11A C12A 1.382(2) . ?
C12A H12A 0.94(2) . ?
C12A C13A 1.382(2) . ?
C13A H13A 0.94(2) . ?
C13A C14A 1.387(2) . ?
C14A H14A 0.90(2) . ?
C14A C15A 1.385(2) . ?
C15A H15A 0.85(2) . ?
N3A C16A 1.343(2) . ?
N3A C20A 1.343(2) . ?
C16A H16A 0.961(19) . ?
C16A C17A 1.389(2) . ?
C17A H17A 0.93(2) . ?
C17A C18A 1.386(3) . ?
C18A H18A 0.90(2) . ?
C18A C19A 1.383(3) . ?
C19A H19A 0.92(2) . ?
C19A C20A 1.386(2) . ?
C20A H20A 0.856(19) . ?
Pd1B Cl1B 2.3116(4) . ?
Pd1B Cl2B 2.3018(4) . ?
Pd1B C1B 1.9497(15) . ?
Pd1B N3B 2.0846(13) . ?
F1B C5B 1.350(2) . ?
F2B C11B 1.3540(19) . ?
N1B C1B 1.3482(19) . ?
N1B C3B 1.397(2) . ?
N1B C4B 1.425(2) . ?
C1B N2B 1.358(2) . ?
N2B C2B 1.402(2) . ?
N2B C10B 1.429(2) . ?
C2B H2B 0.96(2) . ?
C2B C3B 1.343(2) . ?
C3B H3B 0.898(19) . ?
C4B C5B 1.380(2) . ?
C4B C9B 1.389(2) . ?
C5B C6B 1.378(2) . ?
C6B H6B 0.96(2) . ?
C6B C7B 1.383(3) . ?
C7B H7B 0.91(3) . ?
C7B C8B 1.387(3) . ?
C8B H8B 0.85(3) . ?
C8B C9B 1.393(3) . ?
C9B H9B 0.92(2) . ?
C10B C11B 1.387(2) . ?
C10B C15B 1.389(2) . ?
C11B C12B 1.384(2) . ?
C12B H12B 0.92(2) . ?
C12B C13B 1.383(3) . ?
C13B H13B 0.93(3) . ?
C13B C14B 1.384(3) . ?
C14B H14B 0.90(2) . ?
C14B C15B 1.393(3) . ?
C15B H15B 0.96(2) . ?
N3B C16B 1.341(2) . ?
N3B C20B 1.349(2) . ?
C16B H16B 0.94(2) . ?
C16B C17B 1.385(2) . ?
C17B H17B 0.93(2) . ?
C17B C18B 1.382(2) . ?
C18B H18B 0.88(2) . ?
C18B C19B 1.388(2) . ?
C19B H19B 0.96(2) . ?
C19B C20B 1.385(2) . ?
C20B H20B 0.87(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
Cl2A Pd1A Cl1A 174.449(14) . . ?
C1A Pd1A Cl1A 87.15(4) . . ?
C1A Pd1A Cl2A 88.12(4) . . ?
C1A Pd1A N3A 179.29(6) . . ?
N3A Pd1A Cl1A 92.21(4) . . ?
N3A Pd1A Cl2A 92.53(4) . . ?
C1A N1A C3A 110.87(12) . . ?
C1A N1A C4A 123.58(12) . . ?
C3A N1A C4A 125.45(12) . . ?
N1A C1A Pd1A 127.65(10) . . ?
N1A C1A N2A 104.90(12) . . ?
N2A C1A Pd1A 127.44(11) . . ?
C1A N2A C2A 110.80(12) . . ?
C1A N2A C10A 123.66(12) . . ?
C2A N2A C10A 125.45(12) . . ?
N2A C2A H2A 120.7(12) . . ?
C3A C2A N2A 106.58(13) . . ?
C3A C2A H2A 132.7(12) . . ?
N1A C3A H3A 120.7(12) . . ?
C2A C3A N1A 106.85(13) . . ?
C2A C3A H3A 132.5(12) . . ?
C5A C4A N1A 119.51(13) . . ?
C5A C4A C9A 119.03(14) . . ?
C9A C4A N1A 121.43(13) . . ?
F1A C5A C4A 118.59(14) . . ?
F1A C5A C6A 119.47(15) . . ?
C6A C5A C4A 121.94(15) . . ?
C5A C6A H6A 117.9(15) . . ?
C5A C6A C7A 118.60(16) . . ?
C7A C6A H6A 123.5(15) . . ?
C6A C7A H7A 118.7(14) . . ?
C8A C7A C6A 120.65(16) . . ?
C8A C7A H7A 120.6(14) . . ?
C7A C8A H8A 119.3(15) . . ?
C7A C8A C9A 119.89(16) . . ?
C9A C8A H8A 120.8(15) . . ?
C4A C9A C8A 119.89(15) . . ?
C4A C9A H9A 117.1(13) . . ?
C8A C9A H9A 122.9(13) . . ?
C11A C10A N2A 120.63(14) . . ?
C11A C10A C15A 118.74(14) . . ?
C15A C10A N2A 120.63(13) . . ?
F2A C11A C10A 118.78(13) . . ?
F2A C11A C12A 119.25(14) . . ?
C10A C11A C12A 121.97(15) . . ?
C11A C12A H12A 119.3(13) . . ?
C13A C12A C11A 118.71(15) . . ?
C13A C12A H12A 122.0(13) . . ?
C12A C13A H13A 119.0(13) . . ?
C12A C13A C14A 120.30(15) . . ?
C14A C13A H13A 120.7(13) . . ?
C13A C14A H14A 120.9(14) . . ?
C15A C14A C13A 120.14(16) . . ?
C15A C14A H14A 118.9(14) . . ?
C10A C15A H15A 117.5(13) . . ?
C14A C15A C10A 120.12(15) . . ?
C14A C15A H15A 122.3(13) . . ?
C16A N3A Pd1A 120.46(10) . . ?
C16A N3A C20A 118.08(13) . . ?
C20A N3A Pd1A 121.26(11) . . ?
N3A C16A H16A 114.7(11) . . ?
N3A C16A C17A 122.55(16) . . ?
C17A C16A H16A 122.7(11) . . ?
C16A C17A H17A 117.4(13) . . ?
C18A C17A C16A 118.81(16) . . ?
C18A C17A H17A 123.7(13) . . ?
C17A C18A H18A 122.8(14) . . ?
C19A C18A C17A 118.92(15) . . ?
C19A C18A H18A 118.2(14) . . ?
C18A C19A H19A 121.5(13) . . ?
C18A C19A C20A 118.87(16) . . ?
C20A C19A H19A 119.6(13) . . ?
N3A C20A C19A 122.70(15) . . ?
N3A C20A H20A 116.9(13) . . ?
C19A C20A H20A 120.4(13) . . ?
Cl2B Pd1B Cl1B 174.388(16) . . ?
C1B Pd1B Cl1B 86.01(5) . . ?
C1B Pd1B Cl2B 90.41(5) . . ?
C1B Pd1B N3B 175.64(6) . . ?
N3B Pd1B Cl1B 92.77(4) . . ?
N3B Pd1B Cl2B 91.11(4) . . ?
C1B N1B C3B 110.75(13) . . ?
C1B N1B C4B 123.27(13) . . ?
C3B N1B C4B 125.98(13) . . ?
N1B C1B Pd1B 127.68(11) . . ?
N1B C1B N2B 105.28(13) . . ?
N2B C1B Pd1B 126.56(11) . . ?
C1B N2B C2B 110.38(13) . . ?
C1B N2B C10B 123.36(13) . . ?
C2B N2B C10B 126.25(13) . . ?
N2B C2B H2B 120.1(12) . . ?
C3B C2B N2B 106.63(14) . . ?
C3B C2B H2B 133.2(12) . . ?
N1B C3B H3B 121.7(13) . . ?
C2B C3B N1B 106.94(13) . . ?
C2B C3B H3B 131.3(13) . . ?
C5B C4B N1B 119.83(15) . . ?
C5B C4B C9B 119.43(15) . . ?
C9B C4B N1B 120.70(14) . . ?
F1B C5B C4B 118.88(15) . . ?
F1B C5B C6B 119.04(15) . . ?
C6B C5B C4B 122.07(17) . . ?
C5B C6B H6B 119.0(14) . . ?
C5B C6B C7B 118.36(17) . . ?
C7B C6B H6B 122.6(14) . . ?
C6B C7B H7B 120.4(16) . . ?
C6B C7B C8B 120.69(17) . . ?
C8B C7B H7B 118.9(16) . . ?
C7B C8B H8B 120.0(18) . . ?
C7B C8B C9B 120.22(19) . . ?
C9B C8B H8B 119.6(18) . . ?
C4B C9B C8B 119.19(16) . . ?
C4B C9B H9B 119.1(13) . . ?
C8B C9B H9B 121.7(13) . . ?
C11B C10B N2B 120.52(14) . . ?
C11B C10B C15B 118.56(15) . . ?
C15B C10B N2B 120.86(15) . . ?
F2B C11B C10B 118.52(14) . . ?
F2B C11B C12B 119.10(15) . . ?
C12B C11B C10B 122.37(16) . . ?
C11B C12B H12B 121.6(15) . . ?
C13B C12B C11B 118.24(17) . . ?
C13B C12B H12B 120.1(15) . . ?
C12B C13B H13B 119.4(16) . . ?
C12B C13B C14B 120.56(17) . . ?
C14B C13B H13B 120.0(16) . . ?
C13B C14B H14B 119.7(16) . . ?
C13B C14B C15B 120.47(18) . . ?
C15B C14B H14B 119.8(16) . . ?
C10B C15B C14B 119.69(17) . . ?
C10B C15B H15B 117.6(13) . . ?
C14B C15B H15B 122.2(13) . . ?
C16B N3B Pd1B 122.53(11) . . ?
C16B N3B C20B 118.24(14) . . ?
C20B N3B Pd1B 119.18(10) . . ?
N3B C16B H16B 114.0(12) . . ?
N3B C16B C17B 122.38(15) . . ?
C17B C16B H16B 123.6(12) . . ?
C16B C17B H17B 119.9(14) . . ?
C18B C17B C16B 119.34(15) . . ?
C18B C17B H17B 120.8(14) . . ?
C17B C18B H18B 120.0(15) . . ?
C17B C18B C19B 118.69(15) . . ?
C19B C18B H18B 121.3(15) . . ?
C18B C19B H19B 123.4(12) . . ?
C20B C19B C18B 118.91(15) . . ?
C20B C19B H19B 117.7(12) . . ?
N3B C20B C19B 122.44(15) . . ?
N3B C20B H20B 116.3(13) . . ?
C19B C20B H20B 121.2(13) . . ?

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
Pd1A C1A N2A C2A -179.35(11) . . . . ?
Pd1A C1A N2A C10A -2.7(2) . . . . ?
Pd1A N3A C16A C17A -172.55(12) . . . . ?
Pd1A N3A C20A C19A 174.06(12) . . . . ?
F1A C5A C6A C7A -179.42(17) . . . . ?
F2A C11A C12A C13A -178.11(14) . . . . ?
N1A C1A N2A C2A 0.02(17) . . . . ?
N1A C1A N2A C10A 176.69(13) . . . . ?
N1A C4A C5A F1A 0.6(2) . . . . ?
N1A C4A C5A C6A -178.62(16) . . . . ?
N1A C4A C9A C8A 178.97(16) . . . . ?
C1A N1A C3A C2A -0.13(18) . . . . ?
C1A N1A C4A C5A 118.24(17) . . . . ?
C1A N1A C4A C9A -59.9(2) . . . . ?
C1A N2A C2A C3A -0.10(18) . . . . ?
C1A N2A C10A C11A 128.78(16) . . . . ?
C1A N2A C10A C15A -50.5(2) . . . . ?
N2A C2A C3A N1A 0.14(18) . . . . ?
N2A C10A C11A F2A 0.3(2) . . . . ?
N2A C10A C11A C12A -179.12(14) . . . . ?
N2A C10A C15A C14A 177.87(15) . . . . ?
C2A N2A C10A C11A -55.0(2) . . . . ?
C2A N2A C10A C15A 125.63(17) . . . . ?
C3A N1A C1A Pd1A 179.43(11) . . . . ?
C3A N1A C1A N2A 0.06(17) . . . . ?
C3A N1A C4A C5A -57.9(2) . . . . ?
C3A N1A C4A C9A 123.96(17) . . . . ?
C4A N1A C1A Pd1A 2.8(2) . . . . ?
C4A N1A C1A N2A -176.58(13) . . . . ?
C4A N1A C3A C2A 176.43(14) . . . . ?
C4A C5A C6A C7A -0.2(3) . . . . ?
C5A C4A C9A C8A 0.8(3) . . . . ?
C5A C6A C7A C8A 0.4(3) . . . . ?
C6A C7A C8A C9A 0.0(3) . . . . ?
C7A C8A C9A C4A -0.6(3) . . . . ?
C9A C4A C5A F1A 178.81(15) . . . . ?
C9A C4A C5A C6A -0.4(3) . . . . ?
C10A N2A C2A C3A -176.70(14) . . . . ?
C10A C11A C12A C13A 1.3(2) . . . . ?
C11A C10A C15A C14A -1.5(2) . . . . ?
C11A C12A C13A C14A -1.5(2) . . . . ?
C12A C13A C14A C15A 0.3(3) . . . . ?
C13A C14A C15A C10A 1.2(3) . . . . ?
C15A C10A C11A F2A 179.62(14) . . . . ?
C15A C10A C11A C12A 0.2(2) . . . . ?
N3A C16A C17A C18A -1.7(2) . . . . ?
C16A N3A C20A C19A -0.9(2) . . . . ?
C16A C17A C18A C19A -0.6(2) . . . . ?
C17A C18A C19A C20A 2.0(2) . . . . ?
C18A C19A C20A N3A -1.3(3) . . . . ?
C20A N3A C16A C17A 2.5(2) . . . . ?
Pd1B C1B N2B C2B 171.95(11) . . . . ?
Pd1B C1B N2B C10B -9.2(2) . . . . ?
Pd1B N3B C16B C17B 178.17(14) . . . . ?
Pd1B N3B C20B C19B -177.41(13) . . . . ?
F1B C5B C6B C7B 176.04(15) . . . . ?
F2B C11B C12B C13B -177.70(17) . . . . ?
N1B C1B N2B C2B -0.63(17) . . . . ?
N1B C1B N2B C10B 178.20(14) . . . . ?
N1B C4B C5B F1B 0.5(2) . . . . ?
N1B C4B C5B C6B 179.04(15) . . . . ?
N1B C4B C9B C8B -177.21(15) . . . . ?
C1B N1B C3B C2B -0.87(18) . . . . ?
C1B N1B C4B C5B -127.64(16) . . . . ?
C1B N1B C4B C9B 50.2(2) . . . . ?
C1B N2B C2B C3B 0.11(18) . . . . ?
C1B N2B C10B C11B -124.61(17) . . . . ?
C1B N2B C10B C15B 52.6(2) . . . . ?
N2B C2B C3B N1B 0.44(17) . . . . ?
N2B C10B C11B F2B -6.5(2) . . . . ?
N2B C10B C11B C12B 173.42(16) . . . . ?
N2B C10B C15B C14B -174.79(18) . . . . ?
C2B N2B C10B C11B 54.0(2) . . . . ?
C2B N2B C10B C15B -128.72(19) . . . . ?
C3B N1B C1B Pd1B -171.55(12) . . . . ?
C3B N1B C1B N2B 0.92(17) . . . . ?
C3B N1B C4B C5B 51.7(2) . . . . ?
C3B N1B C4B C9B -130.37(17) . . . . ?
C4B N1B C1B Pd1B 7.9(2) . . . . ?
C4B N1B C1B N2B -179.62(14) . . . . ?
C4B N1B C3B C2B 179.68(14) . . . . ?
C4B C5B C6B C7B -2.5(3) . . . . ?
C5B C4B C9B C8B 0.7(2) . . . . ?
C5B C6B C7B C8B 2.1(3) . . . . ?
C6B C7B C8B C9B -0.3(3) . . . . ?
C7B C8B C9B C4B -1.1(3) . . . . ?
C9B C4B C5B F1B -177.42(14) . . . . ?
C9B C4B C5B C6B 1.1(2) . . . . ?
C10B N2B C2B C3B -178.68(15) . . . . ?
C10B C11B C12B C13B 2.4(3) . . . . ?
C11B C10B C15B C14B 2.5(3) . . . . ?
C11B C12B C13B C14B 0.5(3) . . . . ?
C12B C13B C14B C15B -1.8(4) . . . . ?
C13B C14B C15B C10B 0.2(3) . . . . ?
C15B C10B C11B F2B 176.20(16) . . . . ?
C15B C10B C11B C12B -3.9(3) . . . . ?
N3B C16B C17B C18B -1.0(3) . . . . ?
C16B N3B C20B C19B -0.1(3) . . . . ?
C16B C17B C18B C19B 0.2(3) . . . . ?
C17B C18B C19B C20B 0.6(3) . . . . ?
C18B C19B C20B N3B -0.7(3) . . . . ?
C20B N3B C16B C17B 0.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.388
_oxdiff_exptl_absorpt_empirical_full_min 0.811
####################################################################### 
# 
# 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_4c
_database_code_depnum_ccdc_archive 'CCDC 2131076'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-12-27 deposited with the CCDC.	2022-05-12 downloaded from the CCDC.
;
_audit_creation_date             2021-09-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 Cl2 F4 N3 Pd, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C20.50 H14 Cl3 F4 N3 Pd'
_chemical_formula_weight         591.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20.50 H14 Cl3 F4 N3 Pd'
_chemical_oxdiff_usercomment     Pro-193
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'
Pd Pd -0.9988 1.0072 '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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   22.7586(3)
_cell_length_b                   7.15170(10)
_cell_length_c                   26.0618(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4241.89(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    38683
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      35.8010
_cell_measurement_theta_min      2.3740
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.829
_exptl_absorpt_coefficient_mu    1.302
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             2328
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            63848
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.498
_diffrn_reflns_theta_min         2.376
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00  -7.00   0.35    4.21    --  -17.72 -14.00  -3.00  240
  2  ω     44.00  90.55   0.35    4.21    --   17.87 173.00  64.00  133
  3  ω    -89.00  -3.60   0.35    4.21    --  -17.72 -57.00 -90.00  244
  4  ω    -56.00   5.25   0.35    4.21    --   17.87 -19.00 -60.00  175
  5  ω    -56.00   3.15   0.35    4.21    --   17.87 -14.00  -3.00  169
  6  ω    -56.00   3.15   0.35    4.21    --   17.87 -19.00 150.00  169
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0269764000
_diffrn_orient_matrix_UB_12      -0.0024486000
_diffrn_orient_matrix_UB_13      -0.0136135000
_diffrn_orient_matrix_UB_21      -0.0154570000
_diffrn_orient_matrix_UB_22      -0.0179297000
_diffrn_orient_matrix_UB_23      -0.0231145000
_diffrn_orient_matrix_UB_31      -0.0021588000
_diffrn_orient_matrix_UB_32      0.0975131000
_diffrn_orient_matrix_UB_33      -0.0045979000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7935
_reflns_number_total             8926
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.07
_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       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         8926
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0234
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0223P)²+3.0892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0558
_refine_ls_wR_factor_ref         0.0572
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Pd1 Pd 0.37742(2) 0.75258(2) 0.58998(2) 0.01179(2) Uani 1 1 d . . . . .
Cl1 Cl 0.42603(2) 0.51213(4) 0.63166(2) 0.01771(5) Uani 1 1 d . . . . .
Cl2 Cl 0.33563(2) 0.99467(4) 0.54346(2) 0.01810(5) Uani 1 1 d . . . . .
F1 F 0.65339(4) 0.81777(13) 0.66939(4) 0.02836(18) Uani 1 1 d . . . . .
F2 F 0.59013(4) 1.03475(13) 0.73293(3) 0.02633(17) Uani 1 1 d . . . . .
F3 F 0.32633(4) 0.65817(12) 0.33645(3) 0.02466(16) Uani 1 1 d . . . . .
F4 F 0.24443(4) 0.44679(14) 0.38288(3) 0.02963(18) Uani 1 1 d . . . . .
N1 N 0.49767(4) 0.80584(14) 0.54716(4) 0.01244(15) Uani 1 1 d . . . . .
N2 N 0.43927(4) 0.69051(14) 0.49037(4) 0.01221(15) Uani 1 1 d . . . . .
N3 N 0.30928(4) 0.74717(14) 0.64356(4) 0.01444(17) Uani 1 1 d . . . . .
C1 C 0.44117(5) 0.75111(15) 0.53966(4) 0.01214(17) Uani 1 1 d . . . . .
C2 C 0.49450(5) 0.70526(16) 0.46741(4) 0.01363(18) Uani 1 1 d . . . . .
H2 H 0.5017(7) 0.665(2) 0.4344(6) 0.017(4) Uiso 1 1 d . . . . .
C3 C 0.53091(5) 0.77870(16) 0.50277(4) 0.01368(18) Uani 1 1 d . . . . .
H3 H 0.5689(7) 0.814(2) 0.5005(6) 0.016(4) Uiso 1 1 d . . . . .
C4 C 0.52110(5) 0.87271(16) 0.59455(4) 0.01339(18) Uani 1 1 d . . . . .
C5 C 0.57734(5) 0.81497(18) 0.60831(5) 0.0167(2) Uani 1 1 d . . . . .
H5 H 0.5984(9) 0.733(2) 0.5879(7) 0.019(4) Uiso 1 1 d . . . . .
C6 C 0.59979(5) 0.87381(18) 0.65480(5) 0.0186(2) Uani 1 1 d . . . . .
C7 C 0.56717(5) 0.98606(18) 0.68709(5) 0.0182(2) Uani 1 1 d . . . . .
C8 C 0.51183(5) 1.04805(18) 0.67297(5) 0.0175(2) Uani 1 1 d . . . . .
H8 H 0.4905(7) 1.130(2) 0.6958(6) 0.011(3) Uiso 1 1 d . . . . .
C9 C 0.48863(5) 0.99133(17) 0.62600(4) 0.01485(19) Uani 1 1 d . . . . .
H9 H 0.4515(8) 1.035(2) 0.6165(6) 0.019(4) Uiso 1 1 d . . . . .
C10 C 0.38839(5) 0.62458(16) 0.46388(4) 0.01307(18) Uani 1 1 d . . . . .
C11 C 0.38197(5) 0.67543(17) 0.41245(4) 0.0152(2) Uani 1 1 d . . . . .
H11 H 0.4105(9) 0.749(2) 0.3967(8) 0.023(5) Uiso 1 1 d . . . . .
C12 C 0.33336(5) 0.61163(18) 0.38602(5) 0.0176(2) Uani 1 1 d . . . . .
C13 C 0.29141(5) 0.50294(19) 0.41006(5) 0.0197(2) Uani 1 1 d . . . . .
C14 C 0.29776(5) 0.45129(19) 0.46083(5) 0.0193(2) Uani 1 1 d . . . . .
H14 H 0.2698(8) 0.377(3) 0.4760(7) 0.026(5) Uiso 1 1 d . . . . .
C15 C 0.34714(5) 0.51112(17) 0.48806(4) 0.01582(19) Uani 1 1 d . . . . .
H15 H 0.3521(7) 0.476(2) 0.5232(7) 0.018(4) Uiso 1 1 d . . . . .
C16 C 0.31950(5) 0.71986(19) 0.69395(5) 0.0194(2) Uani 1 1 d . . . . .
H16 H 0.3587(9) 0.713(3) 0.7045(7) 0.026(5) Uiso 1 1 d . . . . .
C17 C 0.27446(6) 0.7040(2) 0.72944(5) 0.0243(3) Uani 1 1 d . . . . .
H17 H 0.2850(9) 0.687(3) 0.7648(8) 0.037(5) Uiso 1 1 d . . . . .
C18 C 0.21666(6) 0.7172(2) 0.71270(6) 0.0241(3) Uani 1 1 d . . . . .
H18 H 0.1856(9) 0.711(3) 0.7356(7) 0.028(5) Uiso 1 1 d . . . . .
C19 C 0.20603(5) 0.74483(19) 0.66086(6) 0.0218(2) Uani 1 1 d . . . . .
H19 H 0.1689(9) 0.752(2) 0.6481(8) 0.029(5) Uiso 1 1 d . . . . .
C20 C 0.25326(5) 0.75968(18) 0.62760(5) 0.0179(2) Uani 1 1 d . . . . .
H20 H 0.2490(9) 0.776(2) 0.5899(7) 0.023(5) Uiso 1 1 d . . . . .
Cl3 Cl 0.44145(2) 0.52115(5) 0.27384(2) 0.02585(6) Uani 1 1 d . . . . .
C21 C 0.500000 0.3846(3) 0.250000 0.0235(3) Uani 1 2 d S T P . .
H21 H 0.4856(9) 0.310(3) 0.2232(7) 0.032(5) Uiso 1 1 d . . . . .


_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
Pd1 Cl1 2.3155(3) . ?
Pd1 Cl2 2.3178(3) . ?
Pd1 N3 2.0872(10) . ?
Pd1 C1 1.9558(11) . ?
F1 C6 1.3392(14) . ?
F2 C7 1.3497(14) . ?
F3 C12 1.3436(14) . ?
F4 C13 1.3439(14) . ?
N1 C1 1.3582(14) . ?
N1 C3 1.3958(14) . ?
N1 C4 1.4277(14) . ?
N2 C1 1.3563(14) . ?
N2 C2 1.3962(14) . ?
N2 C10 1.4283(14) . ?
N3 C16 1.3481(16) . ?
N3 C20 1.3441(15) . ?
C2 H2 0.920(17) . ?
C2 C3 1.3459(16) . ?
C3 H3 0.903(16) . ?
C4 C5 1.3918(16) . ?
C4 C9 1.3919(16) . ?
C5 H5 0.927(18) . ?
C5 C6 1.3806(17) . ?
C6 C7 1.3799(18) . ?
C7 C8 1.3849(17) . ?
C8 H8 0.965(15) . ?
C8 C9 1.3935(16) . ?
C9 H9 0.935(17) . ?
C10 C11 1.3963(16) . ?
C10 C15 1.3917(16) . ?
C11 H11 0.929(19) . ?
C11 C12 1.3807(16) . ?
C12 C13 1.3814(18) . ?
C13 C14 1.3814(18) . ?
C14 H14 0.921(19) . ?
C14 C15 1.3962(16) . ?
C15 H15 0.957(17) . ?
C16 H16 0.93(2) . ?
C16 C17 1.3852(18) . ?
C17 H17 0.96(2) . ?
C17 C18 1.389(2) . ?
C18 H18 0.93(2) . ?
C18 C19 1.387(2) . ?
C19 H19 0.91(2) . ?
C19 C20 1.3849(18) . ?
C20 H20 0.994(17) . ?
Cl3 C21 1.7651(11) . ?
C21 H21 0.935(19) 3_655 ?
C21 H21 0.935(19) . ?

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 Pd1 Cl2 175.042(10) . . ?
N3 Pd1 Cl1 91.57(3) . . ?
N3 Pd1 Cl2 93.38(3) . . ?
C1 Pd1 Cl1 87.49(3) . . ?
C1 Pd1 Cl2 87.57(3) . . ?
C1 Pd1 N3 178.63(4) . . ?
C1 N1 C3 110.72(9) . . ?
C1 N1 C4 125.07(9) . . ?
C3 N1 C4 124.13(9) . . ?
C1 N2 C2 110.67(9) . . ?
C1 N2 C10 126.10(9) . . ?
C2 N2 C10 123.21(9) . . ?
C16 N3 Pd1 121.76(8) . . ?
C20 N3 Pd1 119.77(8) . . ?
C20 N3 C16 118.34(10) . . ?
N1 C1 Pd1 127.18(8) . . ?
N2 C1 Pd1 127.81(8) . . ?
N2 C1 N1 104.98(9) . . ?
N2 C2 H2 122.5(11) . . ?
C3 C2 N2 106.88(10) . . ?
C3 C2 H2 130.6(11) . . ?
N1 C3 H3 122.3(11) . . ?
C2 C3 N1 106.74(9) . . ?
C2 C3 H3 130.9(11) . . ?
C5 C4 N1 117.84(10) . . ?
C5 C4 C9 121.14(10) . . ?
C9 C4 N1 121.02(10) . . ?
C4 C5 H5 121.1(12) . . ?
C6 C5 C4 118.43(11) . . ?
C6 C5 H5 120.4(12) . . ?
F1 C6 C5 119.68(12) . . ?
F1 C6 C7 119.41(11) . . ?
C7 C6 C5 120.89(11) . . ?
F2 C7 C6 118.79(11) . . ?
F2 C7 C8 120.32(12) . . ?
C6 C7 C8 120.89(11) . . ?
C7 C8 H8 119.2(9) . . ?
C7 C8 C9 119.00(11) . . ?
C9 C8 H8 121.8(9) . . ?
C4 C9 C8 119.58(10) . . ?
C4 C9 H9 121.8(11) . . ?
C8 C9 H9 118.6(10) . . ?
C11 C10 N2 117.57(10) . . ?
C15 C10 N2 121.36(10) . . ?
C15 C10 C11 121.06(10) . . ?
C10 C11 H11 119.8(12) . . ?
C12 C11 C10 118.46(11) . . ?
C12 C11 H11 121.7(12) . . ?
F3 C12 C11 119.55(11) . . ?
F3 C12 C13 119.54(11) . . ?
C11 C12 C13 120.90(11) . . ?
F4 C13 C12 118.62(11) . . ?
F4 C13 C14 120.55(12) . . ?
C14 C13 C12 120.83(11) . . ?
C13 C14 H14 119.7(11) . . ?
C13 C14 C15 119.28(11) . . ?
C15 C14 H14 121.0(11) . . ?
C10 C15 C14 119.44(11) . . ?
C10 C15 H15 120.5(10) . . ?
C14 C15 H15 120.0(10) . . ?
N3 C16 H16 117.2(12) . . ?
N3 C16 C17 122.32(12) . . ?
C17 C16 H16 120.4(12) . . ?
C16 C17 H17 117.8(13) . . ?
C16 C17 C18 119.04(13) . . ?
C18 C17 H17 123.2(13) . . ?
C17 C18 H18 121.1(12) . . ?
C19 C18 C17 118.75(12) . . ?
C19 C18 H18 120.1(12) . . ?
C18 C19 H19 121.7(13) . . ?
C20 C19 C18 119.03(12) . . ?
C20 C19 H19 119.2(13) . . ?
N3 C20 C19 122.51(12) . . ?
N3 C20 H20 114.0(12) . . ?
C19 C20 H20 123.5(12) . . ?
Cl3 C21 Cl3 112.81(11) 3_655 . ?
Cl3 C21 H21 108.4(12) 3_655 . ?
Cl3 C21 H21 108.4(12) . 3_655 ?
Cl3 C21 H21 108.2(12) . . ?
Cl3 C21 H21 108.2(12) 3_655 3_655 ?
H21 C21 H21 111(2) . 3_655 ?

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
Pd1 N3 C16 C17 -175.76(11) . . . . ?
Pd1 N3 C20 C19 175.73(10) . . . . ?
F1 C6 C7 F2 -0.69(18) . . . . ?
F1 C6 C7 C8 179.34(11) . . . . ?
F2 C7 C8 C9 -178.28(11) . . . . ?
F3 C12 C13 F4 -0.06(19) . . . . ?
F3 C12 C13 C14 179.33(12) . . . . ?
F4 C13 C14 C15 179.76(12) . . . . ?
N1 C4 C5 C6 -177.97(11) . . . . ?
N1 C4 C9 C8 177.43(10) . . . . ?
N2 C2 C3 N1 0.72(13) . . . . ?
N2 C10 C11 C12 179.39(11) . . . . ?
N2 C10 C15 C14 179.41(11) . . . . ?
N3 C16 C17 C18 -0.2(2) . . . . ?
C1 N1 C3 C2 -0.31(13) . . . . ?
C1 N1 C4 C5 139.93(12) . . . . ?
C1 N1 C4 C9 -39.88(17) . . . . ?
C1 N2 C2 C3 -0.92(13) . . . . ?
C1 N2 C10 C11 140.96(12) . . . . ?
C1 N2 C10 C15 -40.12(17) . . . . ?
C2 N2 C1 Pd1 -177.52(8) . . . . ?
C2 N2 C1 N1 0.71(12) . . . . ?
C2 N2 C10 C11 -37.25(16) . . . . ?
C2 N2 C10 C15 141.67(12) . . . . ?
C3 N1 C1 Pd1 178.00(8) . . . . ?
C3 N1 C1 N2 -0.25(12) . . . . ?
C3 N1 C4 C5 -36.53(16) . . . . ?
C3 N1 C4 C9 143.65(11) . . . . ?
C4 N1 C1 Pd1 1.12(16) . . . . ?
C4 N1 C1 N2 -177.12(10) . . . . ?
C4 N1 C3 C2 176.60(10) . . . . ?
C4 C5 C6 F1 178.87(11) . . . . ?
C4 C5 C6 C7 0.47(19) . . . . ?
C5 C4 C9 C8 -2.38(18) . . . . ?
C5 C6 C7 F2 177.72(11) . . . . ?
C5 C6 C7 C8 -2.26(19) . . . . ?
C6 C7 C8 C9 1.70(18) . . . . ?
C7 C8 C9 C4 0.59(17) . . . . ?
C9 C4 C5 C6 1.84(18) . . . . ?
C10 N2 C1 Pd1 4.07(17) . . . . ?
C10 N2 C1 N1 -177.70(10) . . . . ?
C10 N2 C2 C3 177.54(10) . . . . ?
C10 C11 C12 F3 -179.77(11) . . . . ?
C10 C11 C12 C13 1.21(18) . . . . ?
C11 C10 C15 C14 -1.71(18) . . . . ?
C11 C12 C13 F4 178.95(12) . . . . ?
C11 C12 C13 C14 -1.7(2) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C13 C14 C15 C10 1.27(19) . . . . ?
C15 C10 C11 C12 0.47(18) . . . . ?
C16 N3 C20 C19 -0.26(18) . . . . ?
C16 C17 C18 C19 0.4(2) . . . . ?
C17 C18 C19 C20 -0.5(2) . . . . ?
C18 C19 C20 N3 0.4(2) . . . . ?
C20 N3 C16 C17 0.16(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.845
_oxdiff_exptl_absorpt_empirical_full_min 0.543
####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 2131075'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-12-27 deposited with the CCDC.	2022-05-12 downloaded from the CCDC.
;
_audit_creation_date             2021-09-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 Cl2 F2 N3 Pd'
_chemical_formula_sum            'C20 H17 Cl2 F2 N3 Pd'
_chemical_formula_weight         514.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Pd N3 C30 Cl2 F4 H30'
_chemical_oxdiff_usercomment     Pro-187
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'
Pd Pd -0.9988 1.0072 '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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   6.9092(3)
_cell_length_b                   14.7924(6)
_cell_length_c                   9.9257(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.106(5)
_cell_angle_gamma                90
_cell_volume                     1008.69(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7172
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      34.5060
_cell_measurement_theta_min      2.7320
_shelx_estimated_absorpt_T_max   0.899
_shelx_estimated_absorpt_T_min   0.830
_exptl_absorpt_coefficient_mu    1.213
_exptl_absorpt_correction_T_max  0.49277
_exptl_absorpt_correction_T_min  0.47990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9325
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.493
_diffrn_reflns_theta_min         2.754
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00  85.75   0.35    1.59    --   14.61 178.00-120.00  125
  2  ω     42.00  85.75   0.35    1.59    --   14.61 178.00  30.00  125
  3  ω     42.00  85.75   0.35    1.59    --   14.61 178.00  60.00  125
  4  ω     -1.00  86.15   0.35    1.59    --   14.61  62.00 164.00  249
  5  ω    -60.00 -34.80   0.35    1.59    --   14.61 -19.00  60.00   72
  6  ω    -57.00  29.10   0.35    1.59    --   14.61 -62.00  26.00  246
  7  ω    -87.00   6.10   0.35    1.59    --  -14.45 -77.00 -30.00  266
  8  ω    -60.00   4.05   0.35    1.59    --   14.61 -19.00-120.00  183
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0103884000
_diffrn_orient_matrix_UB_12      0.0032365000
_diffrn_orient_matrix_UB_13      -0.0717055000
_diffrn_orient_matrix_UB_21      -0.0715053000
_diffrn_orient_matrix_UB_22      -0.0345475000
_diffrn_orient_matrix_UB_23      -0.0035546000
_diffrn_orient_matrix_UB_31      -0.0737695000
_diffrn_orient_matrix_UB_32      0.0331016000
_diffrn_orient_matrix_UB_33      0.0028544000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1782
_reflns_number_total             1862
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_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       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    
'SHELXT (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_refine_diff_density_max         0.868
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1862
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.096
_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)+(0.0406P)²+0.4786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0736
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C2-H2 = C4-H4 = C5-H5 = C6-H6 = C8-H8 = C9-H9 = C10-H10 = C11-H11
 0.95 with sigma of 0.02
 C5-F1 \\sim C7-F2
 with sigma of 0.003
 C9-C10_$1 \\sim C9_$1-C10
 with sigma of 0.03
 C4-H5 \\sim C6-H5
 with sigma of 0.003
 C7-H6 \\sim C5-H6
 with sigma of 0.003
 C6-H7 \\sim C8-H7
 with sigma of 0.003
3. Restrained planarity
 C3, C4, C5, H4
 with sigma of 0.003
 C4, C5, C6, H5
 with sigma of 0.003
 C5, C6, C7, H6
 with sigma of 0.003
 C6, C7, C8, H7
 with sigma of 0.003
 C3, C7, C8, H8
 with sigma of 0.003
4. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(N2)
Uanis(F1) = Uanis(F2)
5. Others
 Sof(H5)=Sof(F2)=0.5*(1-FVAR(2))
 Sof(F1)=Sof(H7)=0.5*FVAR(2)
 Fixed Sof: C1(0.25) N1(0.5) C2(0.5) H2(0.5) C3(0.5) C4(0.5) H4(0.5) C5(0.5)
 C6(0.5) C7(0.5) C8(0.5) H8(0.5) N2(0.25) C9(0.5) H9(0.5) C10(0.5) H10(0.5)
 C11(0.25) H11(0.25)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Pd1 Pd 0.500000 0.500000 0.500000 0.02774(9) Uani 1 4 d S T P . .
Cl1 Cl 0.76604(8) 0.500000 0.66328(7) 0.03418(13) Uani 1 2 d S T P . .
C1 C 0.500000 0.6269(16) 0.500000 0.028(2) Uani 0.5 2 d S T P . .
N1 N 0.4709(13) 0.6869(7) 0.5938(10) 0.0240(16) Uani 0.5 1 d . . P . .
C2 C 0.4759(10) 0.7756(4) 0.5633(5) 0.0335(12) Uani 0.5 1 d D . P . .
H2 H 0.460(8) 0.819(3) 0.631(4) 0.040 Uiso 0.5 1 d D U P . .
C3 C 0.4163(5) 0.6556(2) 0.7322(4) 0.0312(7) Uani 0.5 1 d . . P . .
C4 C 0.5067(6) 0.6995(3) 0.8457(5) 0.0389(8) Uani 0.5 1 d D . P A .
H4 H 0.594(2) 0.7477(11) 0.844(5) 0.047 Uiso 0.5 1 d D U P . .
C5 C 0.4639(7) 0.6696(3) 0.9716(4) 0.0456(10) Uani 0.5 1 d D . P . .
H5 H 0.525(2) 0.6992(9) 1.0498(18) 0.055 Uiso 0.052(2) 1 d D U P A 2
F1 F 0.5568(7) 0.7094(3) 1.0795(4) 0.0692(11) Uani 0.448(2) 1 d D . P A 1
C6 C 0.3375(6) 0.5997(3) 0.9871(4) 0.0427(8) Uani 0.5 1 d D . P A .
H6 H 0.3107(14) 0.5810(6) 1.0727(16) 0.051 Uiso 1 1 d D U . . .
C7 C 0.2501(6) 0.5572(2) 0.8725(4) 0.0386(8) Uani 0.5 1 d D . P . .
H7 H 0.1496(19) 0.500000 0.8825(6) 0.046 Uiso 0.896(5) 2 d DS U P A 1
F2 F 0.1166(17) 0.500000 0.9066(18) 0.0692(11) Uani 0.104(5) 2 d DS T P A 2
C8 C 0.2864(5) 0.5853(2) 0.7439(4) 0.0323(6) Uani 0.5 1 d D . P A .
H8 H 0.225(3) 0.5574(19) 0.667(3) 0.039 Uiso 0.5 1 d D U P . .
N2 N 0.500000 0.3563(13) 0.500000 0.028(2) Uani 0.5 2 d S T P . .
C9 C 0.465(2) 0.3151(7) 0.6222(14) 0.028(2) Uani 0.5 1 d D . P . .
H9 H 0.453(9) 0.352(3) 0.699(4) 0.033 Uiso 0.5 1 d D U P . .
C10 C 0.4745(9) 0.2176(4) 0.6155(8) 0.0398(14) Uani 0.5 1 d D . P . .
H10 H 0.452(8) 0.192(3) 0.701(3) 0.048 Uiso 0.5 1 d D U P . .
C11 C 0.500000 0.1705(3) 0.500000 0.0441(14) Uani 0.5 2 d DS T P . .
H11 H 0.500000 0.1060(14) 0.500000 0.053 Uiso 0.5 2 d DS 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
Pd1 Cl1 2.3176(6) . ?
Pd1 C1 1.88(2) . ?
Pd1 N2 2.126(19) . ?
C1 N1 1.317(19) . ?
N1 C2 1.348(12) . ?
N1 C3 1.535(11) . ?
C2 C2 1.334(12) 2_656 ?
C2 H2 0.94(2) . ?
C3 C4 1.389(5) . ?
C3 C8 1.387(5) . ?
C4 H4 0.938(19) . ?
C4 C5 1.387(6) . ?
C5 H5 0.95(2) . ?
C5 F1 1.327(6) . ?
C5 C6 1.373(6) . ?
C6 H6 0.931(16) . ?
C6 C7 1.382(6) . ?
C7 H7 1.106(9) . ?
C7 F2 1.322(6) . ?
C7 C8 1.389(6) . ?
C8 H8 0.932(19) . ?
N2 C9 1.401(15) . ?
C9 H9 0.94(2) . ?
C9 C10 1.446(12) . ?
C10 H10 0.96(2) . ?
C10 C11 1.369(8) . ?
C11 H11 0.95(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
Cl1 Pd1 Cl1 180.00(3) 5_666 . ?
C1 Pd1 Cl1 90.000(1) . . ?
C1 Pd1 N2 180.0 . . ?
N2 Pd1 Cl1 90.000(1) . . ?
N1 C1 Pd1 132.4(9) . . ?
C1 N1 C2 119.2(11) . . ?
C1 N1 C3 120.0(10) . . ?
C2 N1 C3 120.6(7) . . ?
N1 C2 H2 119(4) . . ?
C2 C2 N1 103.1(5) 2_656 . ?
C2 C2 H2 137(4) 2_656 . ?
C4 C3 N1 117.0(5) . . ?
C8 C3 N1 121.6(5) . . ?
C8 C3 C4 121.4(4) . . ?
C3 C4 H4 125(3) . . ?
C5 C4 C3 117.5(4) . . ?
C5 C4 H4 117(3) . . ?
C4 C5 H5 118.0(5) . . ?
F1 C5 C4 117.1(4) . . ?
F1 C5 C6 120.2(4) . . ?
C6 C5 C4 122.7(4) . . ?
C6 C5 H5 119.3(5) . . ?
C5 C6 H6 121.2(5) . . ?
C5 C6 C7 118.5(4) . . ?
C7 C6 H6 120.3(5) . . ?
C6 C7 H7 119.8(5) . . ?
C6 C7 C8 121.0(3) . . ?
F2 C7 C6 109.6(8) . . ?
F2 C7 C8 128.7(9) . . ?
C8 C7 H7 119.2(5) . . ?
C3 C8 C7 118.9(3) . . ?
C3 C8 H8 120(3) . . ?
C7 C8 H8 121(3) . . ?
C9 N2 Pd1 115.8(8) . . ?
C9 N2 C9 128.5(17) 2_656 . ?
N2 C9 H9 119(3) . . ?
N2 C9 C10 112.4(11) . . ?
C10 C9 H9 128(3) . . ?
C9 C10 H10 110(3) . . ?
C11 C10 C9 123.8(7) . . ?
C11 C10 H10 126(3) . . ?
C10 C11 C10 118.8(6) . 2_656 ?
C10 C11 H11 120.6(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
Pd1 C1 N1 C2 -178.6(4) . . . . ?
Pd1 C1 N1 C3 -3.3(10) . . . . ?
Pd1 N2 C9 C10 -177.8(6) . . . . ?
Cl1 Pd1 C1 N1 -63.9(5) . . . . ?
Cl1 Pd1 C1 N1 116.1(5) . . . 2_656 ?
C1 N1 C2 C2 -3.5(11) . . . 2_656 ?
C1 N1 C3 C4 137.8(6) . . . . ?
C1 N1 C3 C8 -40.6(9) . . . . ?
N1 C1 N1 C2 1.4(4) 2_656 . . . ?
N1 C1 N1 C3 176.7(10) 2_656 . . . ?
N1 C3 C4 C5 -177.7(5) . . . . ?
N1 C3 C8 C7 176.9(5) . . . . ?
C2 N1 C3 C4 -47.0(9) . . . . ?
C2 N1 C3 C8 134.6(7) . . . . ?
C3 N1 C2 C2 -178.8(7) . . . 2_656 ?
C3 C4 C5 F1 177.3(4) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C4 C3 C8 C7 -1.4(5) . . . . ?
C4 C5 C6 C7 0.2(7) . . . . ?
C5 C6 C7 F2 -172.3(5) . . . . ?
C5 C6 C7 C8 -1.0(6) . . . . ?
F1 C5 C6 C7 -177.1(4) . . . . ?
C6 C7 C8 C3 1.5(5) . . . . ?
F2 C7 C8 C3 171.0(5) . . . . ?
C8 C3 C4 C5 0.7(6) . . . . ?
N2 C9 C10 C11 -4.7(13) . . . . ?
C9 N2 C9 C10 2.2(6) 2_656 . . . ?
C9 C10 C11 C10 2.6(7) . . . 2_656 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.289
_oxdiff_exptl_absorpt_empirical_full_min 0.596
####################################################################### 
# 
# 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_4a_1
_database_code_depnum_ccdc_archive 'CCDC 2131073'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-12-27 deposited with the CCDC.	2022-05-12 downloaded from the CCDC.
;
_audit_creation_date             2021-09-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 Cl2 F2 N3 Pd'
_chemical_formula_sum            'C20 H15 Cl2 F2 N3 Pd'
_chemical_formula_weight         512.65
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     Pro_4b_O-F
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'
Pd Pd -0.9988 1.0072 '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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.2541(2)
_cell_length_b                   14.2448(2)
_cell_length_c                   24.6718(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3955.20(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    41862
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      35.3080
_cell_measurement_theta_min      2.4290
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.747
_exptl_absorpt_coefficient_mu    1.237
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.106a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            76516
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.992
_diffrn_reflns_theta_min         2.450
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     41.00 108.90   0.35    1.70    --   26.74 178.00 150.00  194
  2  ω      0.00 101.15   0.35    1.70    --   26.74  57.00 -30.00  289
  3  ω    -59.00   4.00   0.35    1.70    --   26.74 -19.00 -90.00  180
  4  ω    -52.00  32.00   0.35    1.70    --   26.74 -48.00-157.00  240
  5  ω   -101.00   7.15   0.35    1.70    --  -26.43 -77.00  30.00  309
  6  ω   -111.00 -63.75   0.35    1.70    --  -26.43-178.00 120.00  135
  7  ω   -111.00 -85.80   0.35    1.70    --  -26.43-178.00-150.00   72
  8  ω   -101.00   7.15   0.35    1.70    --  -26.43 -77.00-180.00  309
  9  ω   -105.00 -51.80   0.35    1.70    --  -26.43 157.00  14.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0076829000
_diffrn_orient_matrix_UB_12      -0.0033813000
_diffrn_orient_matrix_UB_13      0.0284628000
_diffrn_orient_matrix_UB_21      0.0507073000
_diffrn_orient_matrix_UB_22      0.0293925000
_diffrn_orient_matrix_UB_23      -0.0017229000
_diffrn_orient_matrix_UB_31      -0.0365971000
_diffrn_orient_matrix_UB_32      0.0400752000
_diffrn_orient_matrix_UB_33      0.0036518000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7332
_reflns_number_total             8463
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.07
_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       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         8463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0245
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²+1.7222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0642
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Pd1 Pd 0.53069(2) 0.63708(2) 0.63049(2) 0.01512(3) Uani 1 1 d . . . . .
Cl1 Cl 0.70305(3) 0.57093(2) 0.59631(2) 0.02117(6) Uani 1 1 d . . . . .
Cl2 Cl 0.36927(3) 0.72000(2) 0.66248(2) 0.02345(6) Uani 1 1 d . . . . .
F1 F 0.53648(8) 0.81755(6) 0.79917(4) 0.03080(18) Uani 1 1 d . . . . .
F2 F 0.87305(9) 0.80159(7) 0.56331(4) 0.0381(2) Uani 1 1 d . . . . .
N1 N 0.66021(9) 0.74462(7) 0.71267(4) 0.01845(18) Uani 1 1 d . . . . .
N2 N 0.68606(10) 0.80821(7) 0.63457(4) 0.01874(18) Uani 1 1 d . . . . .
N3 N 0.42408(10) 0.52349(7) 0.60598(4) 0.01830(18) Uani 1 1 d . . . . .
C1 C 0.63026(10) 0.73671(8) 0.65985(5) 0.01703(19) Uani 1 1 d . . . . .
C2 C 0.75227(13) 0.86084(9) 0.67151(5) 0.0223(2) Uani 1 1 d . . . . .
H2 H 0.7944(17) 0.9157(13) 0.6591(7) 0.027(4) Uiso 1 1 d . . . . .
C3 C 0.73592(12) 0.82120(9) 0.72049(5) 0.0228(2) Uani 1 1 d . . . . .
H3 H 0.7655(19) 0.8396(15) 0.7557(8) 0.038(5) Uiso 1 1 d . . . . .
C4 C 0.60994(11) 0.68511(8) 0.75328(5) 0.0191(2) Uani 1 1 d . . . . .
C5 C 0.54320(12) 0.72311(9) 0.79491(5) 0.0227(2) Uani 1 1 d . . . . .
C6 C 0.48103(13) 0.66743(12) 0.83100(6) 0.0284(3) Uani 1 1 d . . . . .
H6 H 0.437(2) 0.6974(15) 0.8586(8) 0.036(5) Uiso 1 1 d . . . . .
C7 C 0.48523(13) 0.57065(11) 0.82458(6) 0.0289(3) Uani 1 1 d . . . . .
H7 H 0.4398(17) 0.5347(13) 0.8476(8) 0.029(5) Uiso 1 1 d . . . . .
C8 C 0.55310(13) 0.53062(10) 0.78356(6) 0.0264(3) Uani 1 1 d . . . . .
H8 H 0.5571(17) 0.4673(14) 0.7798(8) 0.030(5) Uiso 1 1 d . . . . .
C9 C 0.61696(12) 0.58775(9) 0.74826(5) 0.0227(2) Uani 1 1 d . . . . .
H9 H 0.6672(17) 0.5628(12) 0.7214(7) 0.026(4) Uiso 1 1 d . . . . .
C10 C 0.67087(12) 0.82895(8) 0.57822(5) 0.0210(2) Uani 1 1 d . . . . .
C11 C 0.76688(14) 0.82572(9) 0.54355(6) 0.0270(3) Uani 1 1 d . . . . .
C12 C 0.75514(19) 0.84654(11) 0.48885(6) 0.0368(4) Uani 1 1 d . . . . .
H12 H 0.822(2) 0.8434(14) 0.4680(8) 0.035(5) Uiso 1 1 d . . . . .
C13 C 0.6441(2) 0.86954(11) 0.46901(6) 0.0415(4) Uani 1 1 d . . . . .
H13 H 0.630(2) 0.8863(18) 0.4309(11) 0.066(8) Uiso 1 1 d . . . . .
C14 C 0.54628(19) 0.87245(12) 0.50293(7) 0.0387(4) Uani 1 1 d . . . . .
H14 H 0.473(2) 0.8923(18) 0.4877(11) 0.051(7) Uiso 1 1 d . . . . .
C15 C 0.55926(16) 0.85261(10) 0.55807(6) 0.0290(3) Uani 1 1 d . . . . .
H15 H 0.499(2) 0.8697(14) 0.5838(10) 0.035 Uiso 1 1 d . U . . .
C16 C 0.32402(12) 0.50328(9) 0.63357(5) 0.0224(2) Uani 1 1 d . . . . .
H16 H 0.3082(15) 0.5416(11) 0.6637(7) 0.018(4) Uiso 1 1 d . . . . .
C17 C 0.25105(13) 0.42904(10) 0.61940(6) 0.0269(3) Uani 1 1 d . . . . .
H17 H 0.1809(19) 0.4152(14) 0.6418(8) 0.034(5) Uiso 1 1 d . . . . .
C18 C 0.28007(13) 0.37432(10) 0.57492(6) 0.0280(3) Uani 1 1 d . . . . .
H18 H 0.2298(17) 0.3234(13) 0.5648(7) 0.028(4) Uiso 1 1 d . . . . .
C19 C 0.38289(13) 0.39447(10) 0.54649(6) 0.0258(2) Uani 1 1 d . . . . .
H19 H 0.4095(18) 0.3568(12) 0.5180(8) 0.028(5) Uiso 1 1 d . . . . .
C20 C 0.45334(12) 0.46876(9) 0.56372(5) 0.0217(2) Uani 1 1 d . . . . .
H20 H 0.5243(14) 0.4835(12) 0.5473(7) 0.017(4) Uiso 1 1 d . . . . .


_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
Pd1 Cl1 2.3155(3) . ?
Pd1 Cl2 2.3061(3) . ?
Pd1 N3 2.1031(10) . ?
Pd1 C1 1.9481(11) . ?
F1 C5 1.3515(16) . ?
F2 C11 1.3355(19) . ?
N1 C1 1.3506(15) . ?
N1 C3 1.3977(16) . ?
N1 C4 1.4291(15) . ?
N2 C1 1.3494(15) . ?
N2 C2 1.3958(16) . ?
N2 C10 1.4314(15) . ?
N3 C16 1.3471(17) . ?
N3 C20 1.3428(16) . ?
C2 H2 0.964(19) . ?
C2 C3 1.3463(18) . ?
C3 H3 0.97(2) . ?
C4 C5 1.3829(18) . ?
C4 C9 1.3946(18) . ?
C5 C6 1.383(2) . ?
C6 H6 0.94(2) . ?
C6 C7 1.389(2) . ?
C7 H7 0.92(2) . ?
C7 C8 1.390(2) . ?
C8 H8 0.908(19) . ?
C8 C9 1.3919(19) . ?
C9 H9 0.941(18) . ?
C10 C11 1.3789(19) . ?
C10 C15 1.392(2) . ?
C11 C12 1.388(2) . ?
C12 H12 0.91(2) . ?
C12 C13 1.381(3) . ?
C13 H13 0.98(3) . ?
C13 C14 1.384(3) . ?
C14 H14 0.95(2) . ?
C14 C15 1.397(2) . ?
C15 H15 0.96(2) . ?
C16 H16 0.939(16) . ?
C16 C17 1.3838(19) . ?
C17 H17 0.98(2) . ?
C17 C18 1.385(2) . ?
C18 H18 0.954(19) . ?
C18 C19 1.383(2) . ?
C19 H19 0.934(19) . ?
C19 C20 1.3891(18) . ?
C20 H20 0.920(17) . ?

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
Cl2 Pd1 Cl1 173.202(12) . . ?
N3 Pd1 Cl1 93.45(3) . . ?
N3 Pd1 Cl2 92.47(3) . . ?
C1 Pd1 Cl1 87.13(4) . . ?
C1 Pd1 Cl2 87.29(4) . . ?
C1 Pd1 N3 174.62(4) . . ?
C1 N1 C3 110.51(10) . . ?
C1 N1 C4 121.88(10) . . ?
C3 N1 C4 127.41(10) . . ?
C1 N2 C2 110.60(10) . . ?
C1 N2 C10 123.31(10) . . ?
C2 N2 C10 125.96(10) . . ?
C16 N3 Pd1 119.74(8) . . ?
C20 N3 Pd1 122.01(9) . . ?
C20 N3 C16 118.25(11) . . ?
N1 C1 Pd1 124.27(9) . . ?
N2 C1 Pd1 130.22(9) . . ?
N2 C1 N1 105.48(10) . . ?
N2 C2 H2 119.3(11) . . ?
C3 C2 N2 106.73(11) . . ?
C3 C2 H2 133.9(11) . . ?
N1 C3 H3 123.1(13) . . ?
C2 C3 N1 106.66(11) . . ?
C2 C3 H3 130.3(13) . . ?
C5 C4 N1 120.24(11) . . ?
C5 C4 C9 119.08(11) . . ?
C9 C4 N1 120.34(11) . . ?
F1 C5 C4 118.55(11) . . ?
F1 C5 C6 119.51(12) . . ?
C6 C5 C4 121.91(13) . . ?
C5 C6 H6 118.1(13) . . ?
C5 C6 C7 118.61(14) . . ?
C7 C6 H6 123.3(13) . . ?
C6 C7 H7 117.6(12) . . ?
C6 C7 C8 120.60(13) . . ?
C8 C7 H7 121.8(12) . . ?
C7 C8 H8 120.6(12) . . ?
C7 C8 C9 119.96(13) . . ?
C9 C8 H8 119.4(12) . . ?
C4 C9 H9 118.1(11) . . ?
C8 C9 C4 119.78(12) . . ?
C8 C9 H9 122.1(11) . . ?
C11 C10 N2 120.13(12) . . ?
C11 C10 C15 119.58(12) . . ?
C15 C10 N2 120.29(12) . . ?
F2 C11 C10 118.90(12) . . ?
F2 C11 C12 119.67(15) . . ?
C10 C11 C12 121.43(16) . . ?
C11 C12 H12 117.4(13) . . ?
C13 C12 C11 118.78(16) . . ?
C13 C12 H12 123.8(13) . . ?
C12 C13 H13 122.6(16) . . ?
C12 C13 C14 120.83(14) . . ?
C14 C13 H13 116.5(17) . . ?
C13 C14 H14 117.5(15) . . ?
C13 C14 C15 119.98(18) . . ?
C15 C14 H14 122.4(16) . . ?
C10 C15 C14 119.41(16) . . ?
C10 C15 H15 117.6(14) . . ?
C14 C15 H15 121.2(14) . . ?
N3 C16 H16 115.7(10) . . ?
N3 C16 C17 122.12(12) . . ?
C17 C16 H16 122.1(10) . . ?
C16 C17 H17 119.2(12) . . ?
C16 C17 C18 119.36(13) . . ?
C18 C17 H17 121.4(12) . . ?
C17 C18 H18 119.8(11) . . ?
C19 C18 C17 118.84(12) . . ?
C19 C18 H18 121.4(11) . . ?
C18 C19 H19 122.0(12) . . ?
C18 C19 C20 118.71(12) . . ?
C20 C19 H19 119.0(12) . . ?
N3 C20 C19 122.68(12) . . ?
N3 C20 H20 115.0(11) . . ?
C19 C20 H20 122.3(11) . . ?

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
Pd1 N3 C16 C17 -179.60(11) . . . . ?
Pd1 N3 C20 C19 -178.90(10) . . . . ?
F1 C5 C6 C7 177.41(13) . . . . ?
F2 C11 C12 C13 178.74(13) . . . . ?
N1 C4 C5 F1 -6.31(18) . . . . ?
N1 C4 C5 C6 171.82(12) . . . . ?
N1 C4 C9 C8 -170.59(12) . . . . ?
N2 C2 C3 N1 0.22(15) . . . . ?
N2 C10 C11 F2 1.05(18) . . . . ?
N2 C10 C11 C12 -179.24(12) . . . . ?
N2 C10 C15 C14 -179.90(13) . . . . ?
N3 C16 C17 C18 -1.1(2) . . . . ?
C1 N1 C3 C2 0.11(15) . . . . ?
C1 N1 C4 C5 -118.30(14) . . . . ?
C1 N1 C4 C9 54.92(17) . . . . ?
C1 N2 C2 C3 -0.49(16) . . . . ?
C1 N2 C10 C11 -119.02(14) . . . . ?
C1 N2 C10 C15 61.07(17) . . . . ?
C2 N2 C1 Pd1 -177.46(10) . . . . ?
C2 N2 C1 N1 0.54(14) . . . . ?
C2 N2 C10 C11 65.53(17) . . . . ?
C2 N2 C10 C15 -114.38(15) . . . . ?
C3 N1 C1 Pd1 177.75(9) . . . . ?
C3 N1 C1 N2 -0.40(14) . . . . ?
C3 N1 C4 C5 56.08(18) . . . . ?
C3 N1 C4 C9 -130.70(14) . . . . ?
C4 N1 C1 Pd1 -7.01(16) . . . . ?
C4 N1 C1 N2 174.84(11) . . . . ?
C4 N1 C3 C2 -174.80(12) . . . . ?
C4 C5 C6 C7 -0.7(2) . . . . ?
C5 C4 C9 C8 2.71(19) . . . . ?
C5 C6 C7 C8 1.7(2) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C7 C8 C9 C4 -1.8(2) . . . . ?
C9 C4 C5 F1 -179.61(11) . . . . ?
C9 C4 C5 C6 -1.5(2) . . . . ?
C10 N2 C1 Pd1 6.47(18) . . . . ?
C10 N2 C1 N1 -175.53(11) . . . . ?
C10 N2 C2 C3 175.46(12) . . . . ?
C10 C11 C12 C13 -1.0(2) . . . . ?
C11 C10 C15 C14 0.2(2) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C13 C14 C15 C10 -0.7(2) . . . . ?
C15 C10 C11 F2 -179.04(12) . . . . ?
C15 C10 C11 C12 0.7(2) . . . . ?
C16 N3 C20 C19 2.07(19) . . . . ?
C16 C17 C18 C19 1.3(2) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C18 C19 C20 N3 -1.9(2) . . . . ?
C20 N3 C16 C17 -0.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.485
_oxdiff_exptl_absorpt_empirical_full_min 0.669
