# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_22MA012_ER-0182
_database_code_depnum_ccdc_archive 'CCDC 2297421'
loop_
_audit_author_name
_audit_author_address
'Simon Grabowsky'
;University of Bern
Switzerland
;
_audit_update_record             
;
2023-09-25 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;

_audit_creation_date             2022-02-13T21:43:23-00:00

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'F6 P, C13 H14 N3 O'
_chemical_formula_sum            'C13 H14 F6 N3 O P'
_chemical_formula_weight         373.24

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   21.02657(6)
_cell_length_b                   14.43623(4)
_cell_length_c                   21.17731(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.6664(2)
_cell_angle_gamma                90
_cell_volume                     6427.82(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    173.01(10)
_cell_measurement_reflns_used    172172
_cell_measurement_theta_min      2.975
_cell_measurement_theta_max      79.856

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.338
_exptl_crystal_size_min          0.207
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             3040
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.2465
0 0 -1 0.2403
0 0 1 0.1737
-1 1 -1 0.1357
1 -1 1 0.1661
1 -1 0 0.111
-1 1 0 0.197
-1 1 1 0.2336
1 -1 -1 0.1236
0 -1 0 0.0842
-1 -1 1 0.0718
1 0 -1 0.1891
-1 0 1 0.1676
1 1 0 0.1201
-1 -1 0 0.0868
0 -1 -1 0.1688
0 1 1 0.2133
13 -1 -3 0.1433
-14 0 0 0.1193
2 9 -5 0.1093

loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0004 0.0006 0.9999 0.1008 -0.0234 -0.0081
-0.0005 -0.0006 -1.0001 -0.0517 -0.0114 0.0499
0.0005 0.0006 1.0001 0.0517 0.0114 -0.0499
-1 0.9995 -1.0011 -0.126 -0.0689 -0.0391
1 -0.9995 1.0011 0.126 0.0689 0.0391
0.9996 -1 0.001 0.0743 0.0575 0.089
-0.9996 1 -0.001 -0.0743 -0.0575 -0.089
-0.9991 1.0006 0.999 -0.0226 -0.0461 -0.1389
0.9991 -1.0006 -0.999 0.0226 0.0461 0.1389
-0.0003 -1.0001 0.0012 0.0252 0.0923 0.0472
-0.9998 -0.9995 1.0015 0.0278 0.1385 -0.0445
0.9995 -0.0005 -1.0003 -0.0026 -0.0462 0.0917
-0.9995 0.0005 1.0003 0.0026 0.0462 -0.0917
1.0003 1.0001 -0.0014 0.0239 -0.1271 -0.0054
-1.0003 -1.0001 0.0014 -0.0239 0.1271 0.0054
-0.0008 -1.0006 -0.9988 -0.0265 0.0809 0.0971
0.0008 1.0006 0.9988 0.0265 -0.0809 -0.0971
13.0884 -1.4834 -3.3638 0.5066 -0.357 0.7848
-13.6445 0.0527 -0.0309 -0.6734 0.4695 -0.571
1.8721 8.6496 -4.9712 -0.3826 -0.9202 -0.0829


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.58692
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.449
_shelx_estimated_absorpt_T_max   0.658
_oxdiff_exptl_absorpt_empirical_details 
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.474
_oxdiff_exptl_absorpt_empirical_full_min 0.647

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      173.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0491387
_diffrn_orient_matrix_ub_12      -0.0251555
_diffrn_orient_matrix_ub_13      0.051698
_diffrn_orient_matrix_ub_21      -0.0347942
_diffrn_orient_matrix_ub_22      -0.0922732
_diffrn_orient_matrix_ub_23      0.0114517
_diffrn_orient_matrix_ub_31      0.0417805
_diffrn_orient_matrix_ub_32      -0.0472967
_diffrn_orient_matrix_ub_33      -0.0498859
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_number            246423
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.945
_diffrn_reflns_theta_max         73.994
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             13039
_reflns_number_gt                12544
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
        List of Runs (angles in degrees, time in seconds):
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -95.00  -6.00   0.50    0.40    --  -23.00 -63.00 -56.00  178
  2  ω    -40.00  50.00   0.50    0.40    --  -23.00  63.00  81.00  180
  3  ω     31.00 121.00   0.50    0.40    --   47.92  63.00  81.00  180
  4  ω     96.00 177.00   0.50    1.50    --  113.25  63.00  81.00  162
  5  ω     42.00  71.00   0.50    1.50    --  113.25 -63.00 -56.00   58
  6  ω    -94.00  -8.00   0.50    0.40    --  -23.00 -57.00 120.00  172
  7  ω     -7.00  23.00   0.50    0.40    --   26.00  99.00 -98.25   60
  8  ω      4.00  34.00   0.50    0.40    --   34.00  93.00  72.30   60
  9  ω     13.00  42.00   0.50    0.40    --   42.00  91.00 -43.67   58
 10  ω     17.00  43.00   0.50    0.40    --   46.00  90.00  73.93   52
 11  ω     17.00  43.00   0.50    0.40    --   46.00  90.00-161.81   52
 12  ω     17.00  43.00   0.50    0.40    --   46.00  90.00 158.81   52
 13  ω     17.00  43.00   0.50    0.40    --   46.00  90.00  22.06   52
 14  ω     -1.00  81.00   0.50    0.40    --   47.92 -99.00 -90.00  164
 15  ω    -24.00  65.00   0.50    0.40    --   47.92 -63.00 -56.00  178
 16  ω     27.00 122.00   0.50    0.40    --   50.00  77.00 -80.16  190
 17  ω     32.00 126.00   0.50    0.40    --   54.00  76.00 -30.31  188
 18  ω     31.00 126.00   0.50    0.40    --   54.00  77.00  39.39  190
 19  ω     40.00 135.00   0.50    0.40    --   62.00  76.00 -69.56  190
 20  ω     45.00 139.00   0.50    0.40    --   66.00  73.00 -88.95  188
 21  ω     43.00 139.00   0.50    0.40    --   66.00  77.00 165.06  192
 22  ω     44.00 139.00   0.50    0.40    --   66.00  76.00  69.80  190
 23  ω     43.00 139.00   0.50    0.40    --   66.00  77.00 103.44  192
 24  ω     44.00 139.00   0.50    0.40    --   66.00  76.00-136.13  190
 25  ω     47.00 143.00   0.50    0.40    --   70.00  77.00  42.97  192
 26  ω     48.00 143.00   0.50    0.40    --   70.00  76.00  10.94  190
 27  ω     48.00 143.00   0.50    0.40    --   70.00  76.00-122.20  190
 28  ω     48.00 143.00   0.50    0.40    --   70.00  75.00 -16.98  190
 29  ω     48.00 143.00   0.50    0.40    --   70.00  75.00 -53.56  190
 30  ω     47.00 143.00   0.50    0.40    --   70.00  77.00-168.53  192
 31  ω     48.00 143.00   0.50    0.40    --   70.00  76.00 126.72  190
 32  ω     57.00 146.00   0.50    0.40    --   74.00  62.00  86.98  178
 33  ω     51.00 146.00   0.50    0.40    --   74.00  77.00  19.63  190
 34  ω     59.00 151.00   0.50    0.40    --   78.00  69.00 162.40  184
 35  ω     66.00 154.00   0.50    1.50    --   82.00  60.00-120.80  176
 36  ω     72.00 162.00   0.50    1.50    --   90.00  65.00-123.37  180
 37  ω     68.00 162.00   0.50    1.50    --   90.00  75.00  15.84  188
 38  ω     74.00 162.00   0.50    1.50    --   90.00  60.00 -73.67  176
 39  ω    122.00 148.00   0.50    1.50    --   94.00  77.00   0.46   52
 40  ω     71.00 118.00   0.50    1.50    --   94.00  77.00   0.46   94
 41  ω    131.00 162.00   0.50    1.50    --   94.00  74.00 162.82   62
 42  ω     73.00  98.00   0.50    1.50    --   94.00  74.00 162.82   50
 43  ω     33.00  99.00   0.50    1.50    --  102.00 -80.00  80.79  132
 44  ω     97.00 133.00   0.50    1.50    --  113.25  61.00-120.00   72
 45  ω    131.00 166.00   0.50    1.50    --  113.25  77.00 -30.00   70
 46  ω     80.00 106.00   0.50    1.50    --  113.25 -94.00-150.00   52
 47  ω     91.00 123.00   0.50    1.50    --  113.25  77.00 -30.00   64
 48  ω    123.00 176.00   0.50    1.50    --  113.25  77.00 -60.00  106
 49  ω    152.00 177.00   0.50    1.50    --  113.25  77.00-120.00   50
 50  ω     44.00  69.00   0.50    1.50    --  113.25 -94.00-150.00   50
 51  ω     42.00  72.00   0.50    1.50    --  113.25 -94.00  30.00   60
 52  ω     92.00 118.00   0.50    1.50    --  113.25  77.00 150.00   52
 53  ω    125.00 174.00   0.50    1.50    --  113.25  77.00 150.00   98
 54  ω     97.00 174.00   0.50    1.50    --  113.25  61.00 -30.00  154
 55  ω     91.00 117.00   0.50    1.50    --  113.25  77.00 -60.00   52
 56  ω     46.00 105.00   0.50    1.50    --  113.25 -94.00  60.00  118
 57  ω     91.00 141.00   0.50    1.50    --  113.25  77.00-120.00  100
 58  ω    136.00 168.00   0.50    1.50    --  113.25  61.00-120.00   64
 59  ω     46.00 102.00   0.50    1.50    --  113.25 -77.00 -90.00  112
 60  ω    135.00 177.00   0.50    1.50    --  113.25  77.00 -90.00   84
 61  ω     97.00 159.00   0.50    1.50    --  113.25  61.00  30.00  124
 62  ω     91.00 117.00   0.50    1.50    --  113.25  77.00 -90.00   52
 63  ω    131.00 162.00   0.50    1.50    --  113.25  61.00  60.00   62
 64  ω    136.00 174.00   0.50    1.50    --  113.25  77.00  90.00   76
 65  ω     42.00 105.00   0.50    1.50    --  113.25 -94.00 -30.00  126
 66  ω     91.00 118.00   0.50    1.50    --  113.25  77.00   0.00   54
 67  ω     97.00 123.00   0.50    1.50    --  113.25  61.00  60.00   52
 68  ω     91.00 148.00   0.50    1.50    --  113.25  77.00 120.00  114
 69  ω     91.00 125.00   0.50    1.50    --  113.25  77.00  90.00   68
 70  ω     42.00 106.00   0.50    1.50    --  113.25 -94.00 -90.00  128
 71  ω     78.00 105.00   0.50    1.50    --  113.25 -94.00 120.00   54
 72  ω     97.00 165.00   0.50    1.50    --  113.25  61.00 -90.00  136
 73  ω     80.00 106.00   0.50    1.50    --  113.25 -94.00 150.00   52
 74  ω     97.00 123.00   0.50    1.50    --  113.25  61.00 150.00   52
 75  ω     98.00 164.00   0.50    1.50    --  113.25  61.00 -60.00  132
 76  ω     97.00 122.00   0.50    1.50    --  113.25  61.00  90.00   50
 77  ω    133.00 159.00   0.50    1.50    --  113.25  61.00-150.00   52
 78  ω    128.00 176.00   0.50    1.50    --  113.25  77.00-150.00   96
 79  ω     97.00 122.00   0.50    1.50    --  113.25  61.00-150.00   50
 80  ω    138.00 177.00   0.50    1.50    --  113.25  77.00  30.00   78
 81  ω    126.00 158.00   0.50    1.50    --  113.25  61.00 150.00   64
 82  ω     44.00  70.00   0.50    1.50    --  113.25 -94.00 120.00   52
 83  ω     91.00 120.00   0.50    1.50    --  113.25  77.00-150.00   58
 84  ω     94.00 133.00   0.50    1.50    --  113.25  77.00  30.00   78
 85  ω     73.00 105.00   0.50    1.50    --  113.25 -94.00   0.00   64
 86  ω     42.00  68.00   0.50    1.50    --  113.25 -94.00   0.00   52
 87  ω     42.00  67.00   0.50    1.50    --  113.25 -61.00-150.00   50
 88  ω    137.00 175.00   0.50    1.50    --  113.25  63.00-169.31   76
 89  ω    137.00 173.00   0.50    1.50    --  113.25  61.00-180.00   72
 90  ω     43.00 100.00   0.50    1.50    --  113.25 -77.00 120.00  114
 91  ω     97.00 123.00   0.50    1.50    --  113.25  61.00-180.00   52
 92  ω     96.00 132.00   0.50    1.50    --  113.25  63.00-169.31   72
 93  ω     43.00  85.00   0.50    1.50    --  113.25 -77.00  90.00   84
 94  ω     42.00 106.00   0.50    1.50    --  113.25 -99.00-117.15  128
 95  ω     44.00 102.00   0.50    1.50    --  113.25 -77.00 150.00  116
 96  ω     42.00  67.00   0.50    1.50    --  113.25 -61.00  30.00   50
 97  ω     97.00 171.00   0.50    1.50    --  113.25  61.00   0.00  148
 98  ω    127.00 173.00   0.50    1.50    --  113.25  77.00  60.00   92
 99  ω     91.00 117.00   0.50    1.50    --  113.25  77.00  60.00   52
100  ω     97.00 170.00   0.50    1.50    --  113.25  61.00 120.00  146
101  ω     76.00 106.00   0.50    1.50    --  113.25 -94.00  30.00   60
102  ω    122.00 148.00   0.50    1.50    --  113.25  77.00   0.00   52
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0573P)²+4.0916P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.00025(3)
_refine_ls_number_reflns         13039
_refine_ls_number_parameters     1090
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.05
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.047
_olex2_refinement_description    
;
;

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
P1 P 0.64241(2) 0.25279(3) 0.73712(2) 0.03561(11) Uani 1 1 d . . . . .
P2 P 0.56810(2) 0.78171(3) 0.62162(2) 0.03658(12) Uani 1 1 d . . . . .
P4 P 0.62063(2) 0.71253(3) 0.06250(2) 0.03823(12) Uani 1 1 d . . . . .
P3 P 0.76598(3) 0.72725(4) 0.35512(2) 0.04343(13) Uani 1 1 d . . . . .
F12 F 0.63562(5) 0.76715(9) 0.65516(6) 0.0521(3) Uani 1 1 d . . . . .
F6 F 0.58317(6) 0.23393(9) 0.78173(6) 0.0548(3) Uani 1 1 d . . . . .
F19 F 0.58953(7) 0.80229(9) 0.09477(6) 0.0549(3) Uani 1 1 d . . . . .
F8 F 0.59684(7) 0.86240(10) 0.57981(6) 0.0594(3) Uani 1 1 d . . . . .
F4 F 0.70129(6) 0.27111(10) 0.69178(6) 0.0569(3) Uani 1 1 d . . . . .
F1 F 0.66353(7) 0.33598(9) 0.78173(6) 0.0583(3) Uani 1 1 d . . . . .
O2 O 0.72644(6) 0.44050(9) 0.91278(6) 0.0436(3) Uani 1 1 d . . . . .
F7 F 0.53933(6) 0.69941(11) 0.66250(8) 0.0670(4) Uani 1 1 d . . . . .
F5 F 0.68465(7) 0.18443(10) 0.77857(7) 0.0636(4) Uani 1 1 d . . . . .
F10 F 0.50099(6) 0.79629(12) 0.58694(7) 0.0670(4) Uani 1 1 d . . . . .
F13 F 0.72958(7) 0.73453(10) 0.42018(6) 0.0627(4) Uani 1 1 d . . . . .
O1 O 0.40370(6) 0.00758(10) 0.72046(7) 0.0463(3) Uani 1 1 d . . . . .
F23 F 0.66602(8) 0.70176(10) 0.12244(7) 0.0684(4) Uani 1 1 d . . . . .
O3 O 0.77648(7) 0.46692(11) 0.58701(7) 0.0503(4) Uani 1 1 d . . . . .
F2 F 0.62156(7) 0.16781(11) 0.69339(8) 0.0721(4) Uani 1 1 d . . . . .
F21 F 0.57373(8) 0.72588(11) 0.00346(7) 0.0702(4) Uani 1 1 d . . . . .
F20 F 0.65131(8) 0.62511(10) 0.02982(8) 0.0717(4) Uani 1 1 d . . . . .
F22 F 0.67111(7) 0.77909(11) 0.03033(8) 0.0685(4) Uani 1 1 d . . . . .
F11 F 0.54895(8) 0.85368(12) 0.67422(7) 0.0753(4) Uani 1 1 d . . . . .
F9 F 0.58785(8) 0.70918(11) 0.56848(8) 0.0712(4) Uani 1 1 d . . . . .
O4 O 0.93557(7) 1.01699(11) 0.21754(7) 0.0510(4) Uani 1 1 d . . . . .
F14 F 0.80238(8) 0.71749(12) 0.28981(7) 0.0763(5) Uani 1 1 d . . . . .
F24 F 0.56862(8) 0.65030(11) 0.09569(8) 0.0767(4) Uani 1 1 d . . . . .
F3 F 0.60031(8) 0.32158(13) 0.69599(7) 0.0782(5) Uani 1 1 d . . . . .
N8 N 0.77113(7) 0.56460(11) 0.50380(7) 0.0345(3) Uani 1 1 d . . . . .
N2 N 0.49261(7) 0.09431(11) 0.72451(7) 0.0363(3) Uani 1 1 d . . . . .
F16 F 0.71908(8) 0.64534(11) 0.33433(9) 0.0771(4) Uani 1 1 d . . . . .
F15 F 0.81231(8) 0.65059(14) 0.38388(8) 0.0851(5) Uani 1 1 d . . . . .
N9 N 0.81235(7) 0.69435(10) 0.55690(7) 0.0331(3) Uani 1 1 d . . . . .
F18 F 0.71754(9) 0.79879(12) 0.32426(8) 0.0820(5) Uani 1 1 d . . . . .
N11 N 0.87592(7) 0.92507(12) 0.27973(8) 0.0412(4) Uani 1 1 d . . . . .
N5 N 0.77102(8) 0.57003(12) 0.87289(7) 0.0395(4) Uani 1 1 d . . . . .
N6 N 0.74708(8) 0.51064(11) 0.77151(7) 0.0379(3) Uani 1 1 d . . . . .
N3 N 0.44015(7) 0.23133(11) 0.69126(7) 0.0367(3) Uani 1 1 d . . . . .
N10 N 0.96058(8) 0.92827(11) 0.37147(8) 0.0406(3) Uani 1 1 d . . . . .
N12 N 0.77349(7) 0.96858(11) 0.24506(8) 0.0378(3) Uani 1 1 d . . . . .
N4 N 0.83175(8) 0.60508(12) 0.97952(7) 0.0430(4) Uani 1 1 d . . . . .
N1 N 0.54275(8) -0.01037(12) 0.81457(7) 0.0414(4) Uani 1 1 d . . . . .
N7 N 0.65892(8) 0.49797(12) 0.46809(8) 0.0424(4) Uani 1 1 d . . . . .
F17 F 0.81016(11) 0.81004(16) 0.37377(10) 0.1094(7) Uani 1 1 d . . . . .
C7 C 0.47291(8) 0.15391(12) 0.67559(8) 0.0309(3) Uani 1 1 d . . . . .
C8 C 0.48559(8) 0.13389(12) 0.61339(8) 0.0327(3) Uani 1 1 d . . . . .
C33 C 0.82432(8) 0.61718(11) 0.52273(7) 0.0298(3) Uani 1 1 d . . . . .
C46 C 0.82618(8) 0.91578(12) 0.23604(8) 0.0329(3) Uani 1 1 d . . . . .
C5 C 0.48550(8) -0.03674(12) 0.79330(8) 0.0331(3) Uani 1 1 d . . . . .
C20 C 0.73313(8) 0.57092(12) 0.81813(8) 0.0329(3) Uani 1 1 d . . . . .
C32 C 0.74875(8) 0.49474(12) 0.54007(8) 0.0332(3) Uani 1 1 d . . . . .
C6 C 0.45623(8) 0.02235(12) 0.74288(8) 0.0315(3) Uani 1 1 d . . . . .
C34 C 0.88584(8) 0.59275(12) 0.50781(8) 0.0337(3) Uani 1 1 d . . . . .
C47 C 0.82953(8) 0.85485(13) 0.18610(8) 0.0369(4) Uani 1 1 d . . . . .
C18 C 0.79960(8) 0.52516(12) 0.97826(8) 0.0333(3) Uani 1 1 d . . . . .
C44 C 0.97624(8) 0.97667(12) 0.32018(8) 0.0333(3) Uani 1 1 d . . . . .
C19 C 0.76172(8) 0.50669(12) 0.91932(8) 0.0335(3) Uani 1 1 d . . . . .
C31 C 0.68552(8) 0.45722(12) 0.51850(8) 0.0344(4) Uani 1 1 d . . . . .
C45 C 0.92862(8) 0.97553(12) 0.26710(8) 0.0354(4) Uani 1 1 d . . . . .
C21 C 0.68291(9) 0.63195(14) 0.81257(9) 0.0407(4) Uani 1 1 d . . . . .
C35 C 0.93469(9) 0.65069(13) 0.52857(9) 0.0380(4) Uani 1 1 d . . . . .
C17 C 0.79984(9) 0.46157(14) 1.02688(9) 0.0392(4) Uani 1 1 d . . . . .
C9 C 0.46298(9) 0.19356(14) 0.56721(9) 0.0399(4) Uani 1 1 d . . . . .
C36 C 0.92165(9) 0.72981(14) 0.56221(10) 0.0409(4) Uani 1 1 d . . . . .
C37 C 0.85986(9) 0.75039(14) 0.57623(10) 0.0410(4) Uani 1 1 d . . . . .
C43 C 1.03201(9) 1.02658(13) 0.31426(10) 0.0391(4) Uani 1 1 d . . . . .
C10 C 0.42987(10) 0.27171(14) 0.58338(9) 0.0417(4) Uani 1 1 d . . . . .
C42 C 1.07417(9) 1.02614(14) 0.36518(11) 0.0458(5) Uani 1 1 d . . . . .
C16 C 0.83586(10) 0.48155(15) 1.08039(9) 0.0436(4) Uani 1 1 d . . . . .
C38 C 0.74647(10) 0.71754(16) 0.57608(11) 0.0441(4) Uani 1 1 d . . . . .
C50 C 0.72291(9) 0.96057(15) 0.20507(11) 0.0461(5) Uani 1 1 d . . . . .
C11 C 0.41925(9) 0.29037(14) 0.64597(10) 0.0415(4) Uani 1 1 d . . . . .
C4 C 0.45281(11) -0.11342(14) 0.81517(10) 0.0444(4) Uani 1 1 d . . . . .
C48 C 0.77729(11) 0.84825(16) 0.14597(10) 0.0475(5) Uani 1 1 d . . . . .
C49 C 0.72423(10) 0.90055(15) 0.15583(11) 0.0501(5) Uani 1 1 d . . . . .
C39 C 0.89836(11) 0.50720(15) 0.46985(12) 0.0472(5) Uani 1 1 d . . . . .
C24 C 0.71031(12) 0.50826(16) 0.71847(9) 0.0477(5) Uani 1 1 d . . . . .
C13 C 0.52296(12) 0.04918(16) 0.59674(11) 0.0490(5) Uani 1 1 d . . . . .
C30 C 0.65757(11) 0.38627(16) 0.55213(10) 0.0503(5) Uani 1 1 d . . . . .
C15 C 0.86907(11) 0.56327(17) 1.08291(10) 0.0488(5) Uani 1 1 d . . . . .
C25 C 0.80210(12) 0.44766(17) 0.77701(13) 0.0517(5) Uani 1 1 d . . . . .
C40 C 1.00143(11) 0.93028(16) 0.41999(10) 0.0497(5) Uani 1 1 d . . . . .
C23 C 0.65984(12) 0.56754(18) 0.71179(11) 0.0568(6) Uani 1 1 d . . . . .
C27 C 0.60148(11) 0.46684(17) 0.45021(12) 0.0540(5) Uani 1 1 d . . . . .
C12 C 0.42481(13) 0.25148(19) 0.75818(10) 0.0505(5) Uani 1 1 d . . . . .
C22 C 0.64636(11) 0.62910(18) 0.75854(11) 0.0531(5) Uani 1 1 d . . . . .
C14 C 0.86559(11) 0.62283(17) 1.03197(10) 0.0515(5) Uani 1 1 d . . . . .
C41 C 1.05865(11) 0.97820(15) 0.41848(11) 0.0502(5) Uani 1 1 d . . . . .
C1 C 0.56901(12) -0.06256(19) 0.86013(10) 0.0546(6) Uani 1 1 d . . . . .
C52 C 0.88732(13) 0.7966(2) 0.17714(14) 0.0587(6) Uani 1 1 d . . . . .
C3 C 0.48124(13) -0.16622(17) 0.86226(11) 0.0583(6) Uani 1 1 d . . . . .
C2 C 0.54020(13) -0.13960(18) 0.88502(11) 0.0606(7) Uani 1 1 d . . . . .
C51 C 0.77124(14) 1.03540(18) 0.29781(12) 0.0555(5) Uani 1 1 d . . . . .
C28 C 0.56943(11) 0.39793(18) 0.48142(13) 0.0584(6) Uani 1 1 d . . . . .
C29 C 0.59791(12) 0.35709(19) 0.53318(12) 0.0617(6) Uani 1 1 d . . . . .
C26 C 0.66860(16) 0.6986(2) 0.86488(15) 0.0631(7) Uani 1 1 d . . . . .
H H 0.9766(12) 0.6348(17) 0.5194(11) 0.051(6) Uiso 1 1 d . . . . .
HA H 0.7756(12) 0.4080(18) 1.0242(12) 0.056(7) Uiso 1 1 d . . . . .
HB H 0.5276(12) 0.1036(17) 0.7419(12) 0.052(7) Uiso 1 1 d . . . . .
HC H 0.8388(11) 0.4382(17) 1.1126(11) 0.049(6) Uiso 1 1 d . . . . .
HD H 1.1131(12) 1.0605(17) 0.3613(11) 0.053(7) Uiso 1 1 d . . . . .
HE H 0.8738(11) 0.8986(16) 0.3160(12) 0.047(6) Uiso 1 1 d . . . . .
HF H 1.0404(11) 1.0585(17) 0.2775(11) 0.048(6) Uiso 1 1 d . . . . .
HG H 0.8464(12) 0.8001(18) 0.5988(12) 0.055(7) Uiso 1 1 d . . . . .
HH H 0.7913(12) 0.6162(18) 0.8826(12) 0.052(7) Uiso 1 1 d . . . . .
HI H 0.4708(12) 0.1766(17) 0.5229(12) 0.054(7) Uiso 1 1 d . . . . .
HJ H 0.8810(13) 0.4575(19) 0.4904(12) 0.058(7) Uiso 1 1 d . . . . .
HK H 0.7208(13) 0.7199(18) 0.5410(13) 0.059(7) Uiso 1 1 d . . . . .
HL H 0.8924(13) 0.5809(19) 1.1196(13) 0.067(8) Uiso 1 1 d . . . . .
HM H 0.7453(13) 0.779(2) 0.5958(13) 0.064(8) Uiso 1 1 d . . . . .
HN H 0.9515(13) 0.7705(18) 0.5758(12) 0.057(7) Uiso 1 1 d . . . . .
HO H 0.7802(13) 0.8064(19) 0.1134(13) 0.063(8) Uiso 1 1 d . . . . .
HP H 0.7759(14) 1.004(2) 0.3357(15) 0.072(9) Uiso 1 1 d . . . . .
HQ H 0.6793(14) 0.361(2) 0.5879(14) 0.072(8) Uiso 1 1 d . . . . .
HR H 0.6884(12) 0.9993(18) 0.2152(12) 0.054(7) Uiso 1 1 d . . . . .
HS H 0.7201(11) 0.4649(17) 0.6923(12) 0.049(6) Uiso 1 1 d . . . . .
HT H 0.3981(11) 0.3395(18) 0.6609(11) 0.050(6) Uiso 1 1 d . . . . .
HU H 0.7499(13) 0.5809(19) 0.4719(13) 0.062(8) Uiso 1 1 d . . . . .
HV H 1.0842(12) 0.9768(18) 0.4557(12) 0.057(7) Uiso 1 1 d . . . . .
HW H 0.7338(14) 0.667(2) 0.6046(14) 0.075(9) Uiso 1 1 d . . . . .
HX H 0.4137(12) 0.3134(18) 0.5530(12) 0.058(7) Uiso 1 1 d . . . . .
HY H 0.5614(14) -0.174(2) 0.9183(14) 0.073(8) Uiso 1 1 d . . . . .
HZ H 0.9395(18) 0.501(2) 0.4616(16) 0.094(11) Uiso 1 1 d . . . . .
H1 H 0.8796(15) 0.514(2) 0.4281(16) 0.083(10) Uiso 1 1 d . . . . .
H2 H 0.8871(13) 0.677(2) 1.0323(13) 0.063(7) Uiso 1 1 d . . . . .
H3 H 0.4602(19) 0.255(3) 0.7796(17) 0.098(12) Uiso 1 1 d . . . . .
H4 H 0.6087(13) -0.0454(18) 0.8733(12) 0.055(7) Uiso 1 1 d . . . . .
H5 H 0.4022(17) 0.310(3) 0.7612(16) 0.093(11) Uiso 1 1 d . . . . .
H6 H 0.9878(12) 0.8937(18) 0.4586(12) 0.060(7) Uiso 1 1 d . . . . .
H7 H 0.5872(14) 0.490(2) 0.4157(14) 0.072(9) Uiso 1 1 d . . . . .
H8 H 0.8373(17) 0.479(3) 0.7899(16) 0.093(11) Uiso 1 1 d . . . . .
H9 H 0.4617(15) -0.224(2) 0.8776(14) 0.074(9) Uiso 1 1 d . . . . .
H10 H 0.4120(13) -0.1267(18) 0.7966(12) 0.062(7) Uiso 1 1 d . . . . .
H11 H 0.5777(15) 0.305(2) 0.5561(15) 0.081(9) Uiso 1 1 d . . . . .
H12 H 0.6348(14) 0.564(2) 0.6754(14) 0.077(9) Uiso 1 1 d . . . . .
H13 H 0.6617(15) 0.667(2) 0.9028(16) 0.079(9) Uiso 1 1 d . . . . .
H14 H 0.6883(13) 0.8935(18) 0.1290(12) 0.061(7) Uiso 1 1 d . . . . .
H15 H 0.6111(13) 0.6703(19) 0.7557(12) 0.059(7) Uiso 1 1 d . . . . .
H16 H 0.5633(17) 0.055(2) 0.6128(16) 0.091(11) Uiso 1 1 d . . . . .
H17 H 0.9227(19) 0.839(3) 0.1697(18) 0.111(13) Uiso 1 1 d . . . . .
H18 H 0.5026(15) -0.004(2) 0.6139(15) 0.078(9) Uiso 1 1 d . . . . .
H19 H 0.8048(14) 1.077(2) 0.2934(14) 0.071(9) Uiso 1 1 d . . . . .
H20 H 0.3949(17) 0.205(2) 0.7706(16) 0.087(10) Uiso 1 1 d . . . . .
H21 H 0.5291(14) 0.381(2) 0.4648(13) 0.072(8) Uiso 1 1 d . . . . .
H22 H 0.7935(15) 0.406(2) 0.8098(16) 0.087(10) Uiso 1 1 d . . . . .
H23 H 0.8053(18) 0.415(3) 0.7396(19) 0.108(12) Uiso 1 1 d . . . . .
H24 H 0.7321(16) 1.067(2) 0.2970(14) 0.077(9) Uiso 1 1 d . . . . .
H25 H 0.5264(16) 0.044(2) 0.5545(17) 0.090(10) Uiso 1 1 d . . . . .
H26 H 0.880(2) 0.765(3) 0.141(2) 0.126(15) Uiso 1 1 d . . . . .
H27 H 0.6992(17) 0.743(2) 0.8681(16) 0.083(10) Uiso 1 1 d . . . . .
H28 H 0.8980(18) 0.764(3) 0.2124(19) 0.098(12) Uiso 1 1 d . . . . .
H29 H 0.629(2) 0.720(3) 0.852(2) 0.135(16) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
P1 F6 1.5955(12) . ?
P1 F4 1.5975(13) . ?
P1 F1 1.5882(13) . ?
P1 F5 1.5858(14) . ?
P1 F2 1.5955(13) . ?
P1 F3 1.5846(14) . ?
P2 F12 1.5940(12) . ?
P2 F8 1.5870(13) . ?
P2 F7 1.5935(13) . ?
P2 F10 1.5971(13) . ?
P2 F11 1.5789(15) . ?
P2 F9 1.5958(15) . ?
P4 F19 1.6075(13) . ?
P4 F23 1.5871(13) . ?
P4 F21 1.5949(13) . ?
P4 F20 1.5805(15) . ?
P4 F22 1.5909(14) . ?
P4 F24 1.5858(14) . ?
P3 F13 1.5872(13) . ?
P3 F14 1.5948(14) . ?
P3 F16 1.5983(16) . ?
P3 F15 1.5909(15) . ?
P3 F18 1.5860(16) . ?
P3 F17 1.5617(18) . ?
O2 C19 1.217(2) . ?
O1 C6 1.216(2) . ?
O3 C32 1.215(2) . ?
O4 C45 1.218(2) . ?
N8 C33 1.406(2) . ?
N8 C32 1.355(2) . ?
N8 HU 0.84(3) . ?
N2 C7 1.405(2) . ?
N2 C6 1.350(2) . ?
N2 HB 0.83(3) . ?
N9 C33 1.354(2) . ?
N9 C37 1.346(2) . ?
N9 C38 1.486(2) . ?
N11 C46 1.395(2) . ?
N11 C45 1.355(2) . ?
N11 HE 0.86(2) . ?
N5 C20 1.399(2) . ?
N5 C19 1.359(2) . ?
N5 HH 0.82(3) . ?
N6 C20 1.351(2) . ?
N6 C24 1.357(3) . ?
N6 C25 1.475(3) . ?
N3 C7 1.356(2) . ?
N3 C11 1.352(2) . ?
N3 C12 1.486(2) . ?
N10 C44 1.336(2) . ?
N10 C40 1.332(3) . ?
N12 C46 1.360(2) . ?
N12 C50 1.357(3) . ?
N12 C51 1.477(3) . ?
N4 C18 1.337(2) . ?
N4 C14 1.337(3) . ?
N1 C5 1.336(2) . ?
N1 C1 1.338(3) . ?
N7 C31 1.336(2) . ?
N7 C27 1.339(3) . ?
C7 C8 1.378(2) . ?
C8 C9 1.384(3) . ?
C8 C13 1.498(3) . ?
C33 C34 1.381(2) . ?
C46 C47 1.378(3) . ?
C5 C6 1.494(2) . ?
C5 C4 1.385(3) . ?
C20 C21 1.379(3) . ?
C32 C31 1.502(2) . ?
C34 C35 1.392(3) . ?
C34 C39 1.499(3) . ?
C47 C48 1.384(3) . ?
C47 C52 1.491(3) . ?
C18 C19 1.497(2) . ?
C18 C17 1.380(3) . ?
C44 C45 1.497(2) . ?
C44 C43 1.383(3) . ?
C31 C30 1.382(3) . ?
C21 C22 1.372(3) . ?
C21 C26 1.501(3) . ?
C35 C36 1.375(3) . ?
C35 H 0.93(2) . ?
C17 C16 1.386(3) . ?
C17 HA 0.93(3) . ?
C9 C10 1.371(3) . ?
C9 HI 0.99(3) . ?
C36 C37 1.369(3) . ?
C36 HN 0.91(3) . ?
C37 HG 0.91(3) . ?
C43 C42 1.388(3) . ?
C43 HF 0.92(2) . ?
C10 C11 1.373(3) . ?
C10 HX 0.94(3) . ?
C42 C41 1.367(3) . ?
C42 HD 0.96(3) . ?
C16 C15 1.372(3) . ?
C16 HC 0.93(2) . ?
C38 HK 0.91(3) . ?
C38 HM 0.98(3) . ?
C38 HW 0.98(3) . ?
C50 C49 1.356(3) . ?
C50 HR 0.94(3) . ?
C11 HT 0.90(3) . ?
C4 C3 1.385(3) . ?
C4 H10 0.96(3) . ?
C48 C49 1.365(3) . ?
C48 HO 0.92(3) . ?
C49 H14 0.94(3) . ?
C39 HJ 0.92(3) . ?
C39 HZ 0.89(4) . ?
C39 H1 0.97(3) . ?
C24 C23 1.369(4) . ?
C24 HS 0.86(3) . ?
C13 H16 0.91(4) . ?
C13 H18 0.96(3) . ?
C13 H25 0.90(4) . ?
C30 C29 1.378(3) . ?
C30 HQ 0.96(3) . ?
C15 C14 1.381(3) . ?
C15 HL 0.95(3) . ?
C25 H8 0.91(4) . ?
C25 H22 0.94(4) . ?
C25 H23 0.92(4) . ?
C40 C41 1.389(3) . ?
C40 H6 1.02(3) . ?
C23 C22 1.363(4) . ?
C23 H12 0.93(3) . ?
C27 C28 1.375(4) . ?
C27 H7 0.85(3) . ?
C12 H3 0.87(4) . ?
C12 H5 0.97(4) . ?
C12 H20 0.96(4) . ?
C22 H15 0.95(3) . ?
C14 H2 0.91(3) . ?
C41 HV 0.95(3) . ?
C1 C2 1.374(4) . ?
C1 H4 0.91(3) . ?
C52 H17 0.97(4) . ?
C52 H26 0.91(5) . ?
C52 H28 0.91(4) . ?
C3 C2 1.379(4) . ?
C3 H9 0.99(3) . ?
C2 HY 0.97(3) . ?
C51 HP 0.93(3) . ?
C51 H19 0.93(3) . ?
C51 H24 0.94(3) . ?
C28 C29 1.376(4) . ?
C28 H21 0.95(3) . ?
C29 H11 0.99(3) . ?
C26 H13 0.94(3) . ?
C26 H27 0.91(4) . ?
C26 H29 0.93(5) . ?

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
F6 P1 F4 179.32(8) . . ?
F1 P1 F6 89.52(7) . . ?
F1 P1 F4 91.10(8) . . ?
F1 P1 F2 178.87(10) . . ?
F5 P1 F6 90.13(8) . . ?
F5 P1 F4 90.16(8) . . ?
F5 P1 F1 89.45(8) . . ?
F5 P1 F2 89.50(9) . . ?
F2 P1 F6 90.08(7) . . ?
F2 P1 F4 89.32(8) . . ?
F3 P1 F6 89.84(8) . . ?
F3 P1 F4 89.87(8) . . ?
F3 P1 F1 90.21(9) . . ?
F3 P1 F5 179.66(10) . . ?
F3 P1 F2 90.84(10) . . ?
F12 P2 F10 179.08(8) . . ?
F12 P2 F9 89.42(8) . . ?
F8 P2 F12 90.14(7) . . ?
F8 P2 F7 178.92(9) . . ?
F8 P2 F10 89.24(8) . . ?
F8 P2 F9 89.09(9) . . ?
F7 P2 F12 90.07(7) . . ?
F7 P2 F10 90.53(7) . . ?
F7 P2 F9 89.85(10) . . ?
F11 P2 F12 90.32(8) . . ?
F11 P2 F8 90.72(9) . . ?
F11 P2 F7 90.33(10) . . ?
F11 P2 F10 90.37(9) . . ?
F11 P2 F9 179.68(10) . . ?
F9 P2 F10 89.88(9) . . ?
F23 P4 F19 89.01(8) . . ?
F23 P4 F21 178.13(9) . . ?
F23 P4 F22 90.20(9) . . ?
F21 P4 F19 89.14(8) . . ?
F20 P4 F19 179.14(9) . . ?
F20 P4 F23 91.56(8) . . ?
F20 P4 F21 90.29(8) . . ?
F20 P4 F22 90.97(9) . . ?
F20 P4 F24 91.65(10) . . ?
F22 P4 F19 88.39(8) . . ?
F22 P4 F21 90.05(9) . . ?
F24 P4 F19 88.98(9) . . ?
F24 P4 F23 90.08(9) . . ?
F24 P4 F21 89.58(9) . . ?
F24 P4 F22 177.35(10) . . ?
F13 P3 F14 178.72(9) . . ?
F13 P3 F16 89.19(9) . . ?
F13 P3 F15 90.75(8) . . ?
F14 P3 F16 89.80(10) . . ?
F15 P3 F14 88.43(8) . . ?
F15 P3 F16 87.93(11) . . ?
F18 P3 F13 90.04(9) . . ?
F18 P3 F14 90.72(9) . . ?
F18 P3 F16 88.69(10) . . ?
F18 P3 F15 176.51(12) . . ?
F17 P3 F13 91.22(10) . . ?
F17 P3 F14 89.82(11) . . ?
F17 P3 F16 177.68(13) . . ?
F17 P3 F15 94.35(13) . . ?
F17 P3 F18 89.03(13) . . ?
C33 N8 HU 119.5(19) . . ?
C32 N8 C33 121.36(15) . . ?
C32 N8 HU 118.7(19) . . ?
C7 N2 HB 118.7(18) . . ?
C6 N2 C7 121.35(15) . . ?
C6 N2 HB 119.9(17) . . ?
C33 N9 C38 120.75(15) . . ?
C37 N9 C33 121.02(15) . . ?
C37 N9 C38 118.20(16) . . ?
C46 N11 HE 120.2(16) . . ?
C45 N11 C46 121.95(15) . . ?
C45 N11 HE 117.8(16) . . ?
C20 N5 HH 119.5(17) . . ?
C19 N5 C20 121.37(15) . . ?
C19 N5 HH 116.5(17) . . ?
C20 N6 C24 119.67(18) . . ?
C20 N6 C25 121.08(17) . . ?
C24 N6 C25 119.25(19) . . ?
C7 N3 C12 120.74(17) . . ?
C11 N3 C7 120.51(16) . . ?
C11 N3 C12 118.72(18) . . ?
C40 N10 C44 116.93(17) . . ?
C46 N12 C51 120.37(18) . . ?
C50 N12 C46 119.90(17) . . ?
C50 N12 C51 119.73(19) . . ?
C14 N4 C18 116.49(17) . . ?
C5 N1 C1 116.43(19) . . ?
C31 N7 C27 116.48(18) . . ?
N3 C7 N2 118.07(15) . . ?
N3 C7 C8 120.75(15) . . ?
C8 C7 N2 121.17(16) . . ?
C7 C8 C9 118.46(17) . . ?
C7 C8 C13 120.29(17) . . ?
C9 C8 C13 121.25(17) . . ?
N9 C33 N8 116.38(15) . . ?
N9 C33 C34 120.87(15) . . ?
C34 C33 N8 122.75(15) . . ?
N12 C46 N11 117.30(17) . . ?
N12 C46 C47 120.97(16) . . ?
C47 C46 N11 121.72(17) . . ?
N1 C5 C6 116.13(16) . . ?
N1 C5 C4 124.32(17) . . ?
C4 C5 C6 119.56(17) . . ?
N6 C20 N5 118.26(16) . . ?
N6 C20 C21 121.44(17) . . ?
C21 C20 N5 120.30(17) . . ?
O3 C32 N8 122.90(16) . . ?
O3 C32 C31 122.98(16) . . ?
N8 C32 C31 114.08(15) . . ?
O1 C6 N2 122.51(16) . . ?
O1 C6 C5 122.95(16) . . ?
N2 C6 C5 114.54(15) . . ?
C33 C34 C35 117.65(16) . . ?
C33 C34 C39 120.27(17) . . ?
C35 C34 C39 122.07(17) . . ?
C46 C47 C48 117.89(18) . . ?
C46 C47 C52 120.42(18) . . ?
C48 C47 C52 121.7(2) . . ?
N4 C18 C19 115.75(15) . . ?
N4 C18 C17 124.17(17) . . ?
C17 C18 C19 120.08(16) . . ?
N10 C44 C45 115.83(15) . . ?
N10 C44 C43 124.30(17) . . ?
C43 C44 C45 119.87(17) . . ?
O2 C19 N5 122.62(16) . . ?
O2 C19 C18 123.55(16) . . ?
N5 C19 C18 113.82(15) . . ?
N7 C31 C32 116.42(15) . . ?
N7 C31 C30 124.16(18) . . ?
C30 C31 C32 119.39(17) . . ?
O4 C45 N11 122.73(17) . . ?
O4 C45 C44 123.74(16) . . ?
N11 C45 C44 113.51(15) . . ?
C20 C21 C26 120.5(2) . . ?
C22 C21 C20 118.2(2) . . ?
C22 C21 C26 121.3(2) . . ?
C34 C35 H 118.8(15) . . ?
C36 C35 C34 120.78(17) . . ?
C36 C35 H 120.4(15) . . ?
C18 C17 C16 117.98(18) . . ?
C18 C17 HA 120.8(16) . . ?
C16 C17 HA 121.2(16) . . ?
C8 C9 HI 117.2(15) . . ?
C10 C9 C8 120.47(17) . . ?
C10 C9 HI 122.3(15) . . ?
C35 C36 HN 124.2(17) . . ?
C37 C36 C35 119.22(17) . . ?
C37 C36 HN 116.6(17) . . ?
N9 C37 C36 120.45(17) . . ?
N9 C37 HG 113.5(16) . . ?
C36 C37 HG 126.0(16) . . ?
C44 C43 C42 117.49(19) . . ?
C44 C43 HF 120.4(15) . . ?
C42 C43 HF 122.1(15) . . ?
C9 C10 C11 119.42(18) . . ?
C9 C10 HX 122.3(16) . . ?
C11 C10 HX 118.3(16) . . ?
C43 C42 HD 117.8(15) . . ?
C41 C42 C43 119.18(19) . . ?
C41 C42 HD 123.0(15) . . ?
C17 C16 HC 119.5(15) . . ?
C15 C16 C17 118.94(19) . . ?
C15 C16 HC 121.5(15) . . ?
N9 C38 HK 109.2(17) . . ?
N9 C38 HM 110.4(17) . . ?
N9 C38 HW 105.1(18) . . ?
HK C38 HM 107(2) . . ?
HK C38 HW 111(2) . . ?
HM C38 HW 114(2) . . ?
N12 C50 HR 114.0(15) . . ?
C49 C50 N12 120.76(19) . . ?
C49 C50 HR 125.2(15) . . ?
N3 C11 C10 120.37(18) . . ?
N3 C11 HT 114.0(15) . . ?
C10 C11 HT 125.6(15) . . ?
C5 C4 H10 117.9(16) . . ?
C3 C4 C5 117.9(2) . . ?
C3 C4 H10 124.2(16) . . ?
C47 C48 HO 116.5(17) . . ?
C49 C48 C47 120.8(2) . . ?
C49 C48 HO 122.7(17) . . ?
C50 C49 C48 119.67(19) . . ?
C50 C49 H14 120.5(16) . . ?
C48 C49 H14 119.8(16) . . ?
C34 C39 HJ 108.4(16) . . ?
C34 C39 HZ 111(2) . . ?
C34 C39 H1 109.7(19) . . ?
HJ C39 HZ 114(3) . . ?
HJ C39 H1 110(2) . . ?
HZ C39 H1 102(3) . . ?
N6 C24 C23 120.2(2) . . ?
N6 C24 HS 114.3(16) . . ?
C23 C24 HS 125.3(16) . . ?
C8 C13 H16 109(2) . . ?
C8 C13 H18 109.4(19) . . ?
C8 C13 H25 111(2) . . ?
H16 C13 H18 110(3) . . ?
H16 C13 H25 107(3) . . ?
H18 C13 H25 110(3) . . ?
C31 C30 HQ 119.7(18) . . ?
C29 C30 C31 117.9(2) . . ?
C29 C30 HQ 122.4(18) . . ?
C16 C15 C14 118.87(19) . . ?
C16 C15 HL 121.4(17) . . ?
C14 C15 HL 119.7(17) . . ?
N6 C25 H8 111(2) . . ?
N6 C25 H22 107(2) . . ?
N6 C25 H23 108(2) . . ?
H8 C25 H22 105(3) . . ?
H8 C25 H23 116(3) . . ?
H22 C25 H23 109(3) . . ?
N10 C40 C41 123.0(2) . . ?
N10 C40 H6 115.1(15) . . ?
C41 C40 H6 121.9(15) . . ?
C24 C23 H12 119.0(19) . . ?
C22 C23 C24 120.0(2) . . ?
C22 C23 H12 121.0(19) . . ?
N7 C27 C28 123.5(2) . . ?
N7 C27 H7 115(2) . . ?
C28 C27 H7 122(2) . . ?
N3 C12 H3 108(2) . . ?
N3 C12 H5 110(2) . . ?
N3 C12 H20 106(2) . . ?
H3 C12 H5 109(3) . . ?
H3 C12 H20 117(3) . . ?
H5 C12 H20 105(3) . . ?
C21 C22 H15 117.5(16) . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H15 122.0(16) . . ?
N4 C14 C15 123.5(2) . . ?
N4 C14 H2 115.6(17) . . ?
C15 C14 H2 120.8(17) . . ?
C42 C41 C40 119.11(19) . . ?
C42 C41 HV 123.9(16) . . ?
C40 C41 HV 116.9(16) . . ?
N1 C1 C2 123.5(2) . . ?
N1 C1 H4 115.8(17) . . ?
C2 C1 H4 120.6(16) . . ?
C47 C52 H17 107(2) . . ?
C47 C52 H26 105(3) . . ?
C47 C52 H28 113(2) . . ?
H17 C52 H26 107(3) . . ?
H17 C52 H28 106(3) . . ?
H26 C52 H28 118(3) . . ?
C4 C3 H9 121.6(18) . . ?
C2 C3 C4 118.5(2) . . ?
C2 C3 H9 119.7(18) . . ?
C1 C2 C3 119.3(2) . . ?
C1 C2 HY 119.8(18) . . ?
C3 C2 HY 120.9(18) . . ?
N12 C51 HP 109.1(19) . . ?
N12 C51 H19 108.2(18) . . ?
N12 C51 H24 109.7(19) . . ?
HP C51 H19 109(3) . . ?
HP C51 H24 110(3) . . ?
H19 C51 H24 111(3) . . ?
C27 C28 C29 118.8(2) . . ?
C27 C28 H21 116.6(18) . . ?
C29 C28 H21 124.6(18) . . ?
C30 C29 H11 118.8(18) . . ?
C28 C29 C30 119.2(2) . . ?
C28 C29 H11 122.0(18) . . ?
C21 C26 H13 110(2) . . ?
C21 C26 H27 111(2) . . ?
C21 C26 H29 101(3) . . ?
H13 C26 H27 114(3) . . ?
H13 C26 H29 105(3) . . ?
H27 C26 H29 115(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
O3 C32 C31 N7 176.32(18) . . . . ?
O3 C32 C31 C30 -1.6(3) . . . . ?
N8 C33 C34 C35 179.34(16) . . . . ?
N8 C33 C34 C39 0.1(3) . . . . ?
N8 C32 C31 N7 -1.5(2) . . . . ?
N8 C32 C31 C30 -179.42(18) . . . . ?
N2 C7 C8 C9 177.71(16) . . . . ?
N2 C7 C8 C13 -2.2(3) . . . . ?
N9 C33 C34 C35 -0.7(3) . . . . ?
N9 C33 C34 C39 -179.90(17) . . . . ?
N11 C46 C47 C48 178.29(17) . . . . ?
N11 C46 C47 C52 -0.2(3) . . . . ?
N5 C20 C21 C22 -178.78(17) . . . . ?
N5 C20 C21 C26 0.5(3) . . . . ?
N6 C20 C21 C22 1.1(3) . . . . ?
N6 C20 C21 C26 -179.65(19) . . . . ?
N6 C24 C23 C22 -0.1(3) . . . . ?
N3 C7 C8 C9 -1.4(3) . . . . ?
N3 C7 C8 C13 178.76(17) . . . . ?
N10 C44 C45 O4 179.16(19) . . . . ?
N10 C44 C45 N11 0.4(2) . . . . ?
N10 C44 C43 C42 -0.1(3) . . . . ?
N10 C40 C41 C42 0.3(3) . . . . ?
N12 C46 C47 C48 -0.8(3) . . . . ?
N12 C46 C47 C52 -179.4(2) . . . . ?
N12 C50 C49 C48 -0.7(3) . . . . ?
N4 C18 C19 O2 -174.51(18) . . . . ?
N4 C18 C19 N5 6.5(2) . . . . ?
N4 C18 C17 C16 -0.2(3) . . . . ?
N1 C5 C6 O1 -178.13(17) . . . . ?
N1 C5 C6 N2 1.3(2) . . . . ?
N1 C5 C4 C3 0.1(3) . . . . ?
N1 C1 C2 C3 0.5(4) . . . . ?
N7 C31 C30 C29 -1.4(3) . . . . ?
N7 C27 C28 C29 -1.2(4) . . . . ?
C7 N2 C6 O1 -3.4(3) . . . . ?
C7 N2 C6 C5 177.20(15) . . . . ?
C7 N3 C11 C10 1.3(3) . . . . ?
C7 C8 C9 C10 1.3(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C33 N8 C32 O3 -8.0(3) . . . . ?
C33 N8 C32 C31 169.85(15) . . . . ?
C33 N9 C37 C36 -0.7(3) . . . . ?
C33 C34 C35 C36 -0.6(3) . . . . ?
C46 N11 C45 O4 1.2(3) . . . . ?
C46 N11 C45 C44 179.99(17) . . . . ?
C46 N12 C50 C49 -0.2(3) . . . . ?
C46 C47 C48 C49 -0.1(3) . . . . ?
C5 N1 C1 C2 -0.1(3) . . . . ?
C5 C4 C3 C2 0.3(3) . . . . ?
C20 N5 C19 O2 10.0(3) . . . . ?
C20 N5 C19 C18 -171.02(16) . . . . ?
C20 N6 C24 C23 0.9(3) . . . . ?
C20 C21 C22 C23 -0.2(3) . . . . ?
C32 N8 C33 N9 -90.8(2) . . . . ?
C32 N8 C33 C34 89.2(2) . . . . ?
C32 C31 C30 C29 176.4(2) . . . . ?
C6 N2 C7 N3 92.1(2) . . . . ?
C6 N2 C7 C8 -87.0(2) . . . . ?
C6 C5 C4 C3 -179.56(18) . . . . ?
C34 C35 C36 C37 1.2(3) . . . . ?
C47 C48 C49 C50 0.8(3) . . . . ?
C18 N4 C14 C15 0.8(3) . . . . ?
C18 C17 C16 C15 0.5(3) . . . . ?
C44 N10 C40 C41 -1.3(3) . . . . ?
C44 C43 C42 C41 -0.9(3) . . . . ?
C19 N5 C20 N6 -81.1(2) . . . . ?
C19 N5 C20 C21 98.8(2) . . . . ?
C19 C18 C17 C16 179.72(17) . . . . ?
C31 N7 C27 C28 1.2(3) . . . . ?
C31 C30 C29 C28 1.3(4) . . . . ?
C45 N11 C46 N12 -101.7(2) . . . . ?
C45 N11 C46 C47 79.1(2) . . . . ?
C45 C44 C43 C42 179.27(17) . . . . ?
C35 C36 C37 N9 -0.6(3) . . . . ?
C17 C18 C19 O2 5.5(3) . . . . ?
C17 C18 C19 N5 -173.44(17) . . . . ?
C17 C16 C15 C14 -0.1(3) . . . . ?
C9 C10 C11 N3 -1.3(3) . . . . ?
C37 N9 C33 N8 -178.67(17) . . . . ?
C37 N9 C33 C34 1.3(3) . . . . ?
C43 C44 C45 O4 -0.3(3) . . . . ?
C43 C44 C45 N11 -179.08(17) . . . . ?
C43 C42 C41 C40 0.8(3) . . . . ?
C16 C15 C14 N4 -0.5(4) . . . . ?
C38 N9 C33 N8 3.6(2) . . . . ?
C38 N9 C33 C34 -176.41(17) . . . . ?
C38 N9 C37 C36 177.1(2) . . . . ?
C50 N12 C46 N11 -178.17(16) . . . . ?
C50 N12 C46 C47 1.0(3) . . . . ?
C11 N3 C7 N2 -179.04(16) . . . . ?
C11 N3 C7 C8 0.1(3) . . . . ?
C4 C5 C6 O1 1.6(3) . . . . ?
C4 C5 C6 N2 -179.04(17) . . . . ?
C4 C3 C2 C1 -0.6(3) . . . . ?
C39 C34 C35 C36 178.6(2) . . . . ?
C24 N6 C20 N5 178.42(16) . . . . ?
C24 N6 C20 C21 -1.4(3) . . . . ?
C24 C23 C22 C21 -0.3(3) . . . . ?
C13 C8 C9 C10 -178.78(19) . . . . ?
C25 N6 C20 N5 -2.1(3) . . . . ?
C25 N6 C20 C21 178.04(18) . . . . ?
C25 N6 C24 C23 -178.6(2) . . . . ?
C40 N10 C44 C45 -178.24(18) . . . . ?
C40 N10 C44 C43 1.2(3) . . . . ?
C27 N7 C31 C32 -177.64(18) . . . . ?
C27 N7 C31 C30 0.2(3) . . . . ?
C27 C28 C29 C30 -0.1(4) . . . . ?
C12 N3 C7 N2 -0.9(3) . . . . ?
C12 N3 C7 C8 178.18(18) . . . . ?
C12 N3 C11 C10 -176.9(2) . . . . ?
C14 N4 C18 C19 179.68(19) . . . . ?
C14 N4 C18 C17 -0.4(3) . . . . ?
C1 N1 C5 C6 179.45(17) . . . . ?
C1 N1 C5 C4 -0.2(3) . . . . ?
C52 C47 C48 C49 178.4(2) . . . . ?
C51 N12 C46 N11 2.5(3) . . . . ?
C51 N12 C46 C47 -178.36(18) . . . . ?
C51 N12 C50 C49 179.1(2) . . . . ?
C26 C21 C22 C23 -179.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 HB F6 0.83(3) 2.37(3) 3.017(2) 136(2) . yes
N2 HB F2 0.83(3) 2.42(3) 2.992(2) 127(2) . yes
N11 HE F17 0.86(2) 2.23(2) 2.950(2) 142(2) . yes
C37 HG O2 0.91(3) 2.55(3) 3.300(2) 140(2) 2_656 yes
N5 HH N4 0.82(3) 2.22(2) 2.630(2) 112(2) . yes
C15 HL O1 0.95(3) 2.50(3) 3.164(3) 127(2) 4_666 yes
C38 HM O2 0.98(3) 2.41(3) 3.277(3) 147(2) 2_656 yes
C50 HR O1 0.94(3) 2.38(3) 3.144(3) 138(2) 3_666 yes
C24 HS O3 0.86(3) 2.54(2) 3.183(3) 132(2) . yes
C11 HT O4 0.90(3) 2.52(2) 3.184(3) 131.8(19) 4_576 yes
C11 HT F16 0.90(3) 2.48(2) 3.086(3) 125.5(19) 3_666 yes
N8 HU F13 0.84(3) 2.51(3) 3.143(2) 133(2) . yes
N8 HU F15 0.84(3) 2.50(3) 2.965(2) 116(2) . yes
C2 HY F21 0.97(3) 2.32(3) 3.243(3) 159(2) 1_546 yes
C1 H4 O3 0.91(3) 2.55(3) 3.450(3) 168(2) 2_646 yes


#----------------------------------------------------------------------------#
#                       SHELX RES FILE                                       #
#----------------------------------------------------------------------------#

####################################################################### 
# 
# 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_21MA144_ER-0187
_database_code_depnum_ccdc_archive 'CCDC 2297422'
loop_
_audit_author_name
_audit_author_address
'Simon Grabowsky'
;University of Bern
Switzerland
;
_audit_update_record             
;
2023-09-25 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;

_audit_creation_date             2021-07-26T16:09:13-00:00

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C13 H13 N3 O'
_chemical_formula_sum            'C13 H13 N3 O'
_chemical_formula_weight         227.26

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.25664(8)
_cell_length_b                   9.94244(8)
_cell_length_c                   11.26378(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.5286(7)
_cell_angle_gamma                90
_cell_volume                     1148.226(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173.01(10)
_cell_measurement_reflns_used    18371
_cell_measurement_theta_min      4.299
_cell_measurement_theta_max      79.55

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.075
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             480
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.1153
0 0 -1 0.0773
1 -1 1 0.035
4 1 5 0.0631
-5 0 -5 0.09
4 -5 -1 0.0431
7 0 0 0.0177
-7 0 0 0.0569
5 -3 -3 0.0196
4 4 4 0.0569
-5 -5 0 0.0906
-5 0 5 0.114
4 4 -4 0.0446
-4 -4 4 0.0877
0 -5 -5 0.048
0 5 -5 0.0543
0 5 5 0.0905
0 6 0 0.0761

loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0003 -0.0007 0.9998 -0.1045 0.011 0.0875
-0.0003 0.0007 -0.9998 0.1045 -0.011 -0.0875
1.0004 -1.0009 0.9995 -0.223 -0.1256 -0.0302
4.0014 0.9968 4.9998 -0.5042 -0.553 0.5621
-5.0015 0.0034 -4.9995 0.6227 0.6896 -0.4443
4.0004 -5.0003 -1.0014 -0.4679 -0.5451 -0.6777
7.0002 0.0001 0.0005 -0.1402 -1.0424 0.0093
-7.0002 -0.0001 -0.0005 0.1402 1.0424 -0.0093
4.9997 -2.9985 -3.0002 -0.082 -0.7407 -0.6133
4.0008 3.9981 4.001 -0.1043 -0.6009 0.8319
-4.9997 -5.0012 -0.0022 -0.3921 0.8061 -0.6021
-4.9989 -0.0035 4.9987 -0.4223 0.7996 0.4311
3.9987 4.0037 -3.9975 0.7317 -0.6889 0.1315
-3.9987 -4.0037 3.9975 -0.7317 0.6889 -0.1315
-0.0008 -4.9976 -5.0009 0.0303 0.0065 -1.0332
-0.0018 5.0046 -4.9972 1.0148 -0.1166 0.1578
0.0008 4.9976 5.0009 -0.0303 -0.0065 1.0332
-0.0006 6.0013 0.0022 0.5907 -0.0738 0.7146


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.50923
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.9
_shelx_estimated_absorpt_T_max   0.95
_oxdiff_exptl_absorpt_empirical_details 
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.057
_oxdiff_exptl_absorpt_empirical_full_min 0.669

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      173.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0200267
_diffrn_orient_matrix_ub_12      0.0984681
_diffrn_orient_matrix_ub_13      -0.1044488
_diffrn_orient_matrix_ub_21      -0.1489116
_diffrn_orient_matrix_ub_22      -0.0123244
_diffrn_orient_matrix_ub_23      0.0110355
_diffrn_orient_matrix_ub_31      0.0013151
_diffrn_orient_matrix_ub_32      0.1190388
_diffrn_orient_matrix_ub_33      0.0876428
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_number            22145
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.312
_diffrn_reflns_theta_max         70.234
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             2186
_reflns_number_gt                2108
_reflns_threshold_expression     'I > 2σ(I)'
_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  50.00   0.50    0.22    --  -23.00  67.00  61.00  184
  2  ω    -95.00  -4.00   0.50    0.22    --  -23.00 -67.00 -72.00  182
  3  ω     29.00 120.00   0.50    0.22    --   47.95  67.00  61.00  182
  4  ω     95.00 177.00   0.50    1.00    --  113.25  67.00  61.00  164
  5  ω     42.00  78.00   0.50    1.00    --  113.25 -67.00 -72.00   72
  6  ω    -95.00 -10.00   0.50    0.22    --  -23.00 -45.00 120.00  170
  7  ω    -70.00 -12.00   0.50    0.22    --  -23.00 125.00-180.00  116
  8  ω    -24.00  67.00   0.50    0.22    --   47.95 -67.00 -72.00  182
  9  ω    -26.00  23.00   0.50    0.22    --   47.95 -19.00 120.00   98
 10  ω     36.00 121.00   0.50    0.22    --   47.95  38.00  30.00  170
 11  ω     97.00 177.00   0.50    1.00    --  113.25  61.00 -60.00  160
 12  ω     97.00 177.00   0.50    1.00    --  113.25  61.00 150.00  160
 13  ω     42.00  68.00   0.50    1.00    --  113.25 -61.00  90.00   52
 14  ω     42.00 106.00   0.50    1.00    --  113.25 -94.00  30.00  128
 15  ω     97.00 177.00   0.50    1.00    --  113.25  61.00   0.00  160
 16  ω     91.00 177.00   0.50    1.00    --  113.25  77.00 -90.00  172
 17  ω     42.00 102.00   0.50    1.00    --  113.25 -77.00 -90.00  120
 18  ω     97.00 177.00   0.50    1.00    --  113.25  61.00  30.00  160
 19  ω     97.00 177.00   0.50    1.00    --  113.25  61.00 -30.00  160
 20  ω    101.00 177.00   0.50    1.00    --  113.25  45.00   0.00  152
 21  ω     95.00 177.00   0.50    1.00    --  113.25  67.00  13.92  164
 22  ω    101.00 177.00   0.50    1.00    --  113.25  30.00 -30.00  152
 23  ω    107.00 177.00   0.50    1.00    --  113.25 101.00-106.78  140
 24  ω     91.00 177.00   0.50    1.00    --  113.25  77.00 -30.00  172
 25  ω     91.00 177.00   0.50    1.00    --  113.25  77.00 -60.00  172
 26  ω     42.00  68.00   0.50    1.00    --  113.25 -61.00 -30.00   52
 27  ω     42.00 102.00   0.50    1.00    --  113.25 -77.00-120.00  120
 28  ω    100.00 177.00   0.50    1.00    --  113.25  15.00  90.00  154
 29  ω     42.00  68.00   0.50    1.00    --  113.25 -61.00 -60.00   52
 30  ω     42.00 106.00   0.50    1.00    --  113.25 -94.00-180.00  128
 31  ω     42.00 106.00   0.50    1.00    --  113.25 -94.00  90.00  128
 32  ω     91.00 177.00   0.50    1.00    --  113.25  77.00 156.38  172
 33  ω     91.00 177.00   0.50    1.00    --  113.25  77.00   0.00  172
 34  ω     42.00 102.00   0.50    1.00    --  113.25 -77.00 -30.00  120
 35  ω    101.00 177.00   0.50    1.00    --  113.25  45.00-150.00  152
 36  ω     42.00 106.00   0.50    1.00    --  113.25 -94.00-150.00  128
 37  ω    101.00 177.00   0.50    1.00    --  113.25  38.00 -10.92  152
 38  ω     91.00 177.00   0.50    1.00    --  113.25  77.00  30.00  172
 39  ω     42.00 102.00   0.50    1.00    --  113.25 -77.00  90.00  120
 40  ω    101.00 177.00   0.50    1.00    --  113.25  45.00  30.00  152
 41  ω     25.00 120.00   0.50    0.22    --   47.95  77.00 120.00  190
 42  ω     25.00  99.00   0.50    0.22    --   47.95  77.00 -30.00  148
 43  ω     25.00 120.00   0.50    0.22    --   47.95  77.00-120.00  190
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+0.3331P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0037(4)
_refine_ls_number_reflns         2186
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.032
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0813
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.032
_olex2_refinement_description    
;
;

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.24462(8) 0.48955(8) 0.79861(6) 0.0330(2) Uani 1 1 d . . . . .
N2 N 0.24893(9) 0.50158(9) 0.59415(8) 0.0274(2) Uani 1 1 d . . . . .
N1 N 0.11826(9) 0.24690(9) 0.78316(8) 0.0281(2) Uani 1 1 d . . . . .
N3 N 0.29798(9) 0.70505(9) 0.50760(8) 0.0268(2) Uani 1 1 d . . . . .
C5 C 0.16890(9) 0.30137(10) 0.68541(8) 0.0221(2) Uani 1 1 d . . . . .
C6 C 0.22634(9) 0.44125(10) 0.69828(9) 0.0243(2) Uani 1 1 d . . . . .
C7 C 0.33442(10) 0.60142(10) 0.58264(8) 0.0236(2) Uani 1 1 d . . . . .
C8 C 0.46544(10) 0.60427(10) 0.62986(9) 0.0248(2) Uani 1 1 d . . . . .
C4 C 0.17462(10) 0.23187(11) 0.57878(9) 0.0255(2) Uani 1 1 d . . . . .
C2 C 0.08018(11) 0.04264(11) 0.67272(10) 0.0307(3) Uani 1 1 d . . . . .
C3 C 0.13141(10) 0.10009(11) 0.57248(10) 0.0293(2) Uani 1 1 d . . . . .
C11 C 0.38023(11) 0.80664(10) 0.47742(10) 0.0297(3) Uani 1 1 d . . . . .
C10 C 0.50375(11) 0.81118(11) 0.52343(10) 0.0316(3) Uani 1 1 d . . . . .
C1 C 0.07444(11) 0.12051(11) 0.77435(10) 0.0310(3) Uani 1 1 d . . . . .
C9 C 0.54533(10) 0.70888(11) 0.60055(10) 0.0293(2) Uani 1 1 d . . . . .
C12 C 0.51661(11) 0.48982(12) 0.70373(11) 0.0322(3) Uani 1 1 d . . . . .
C13 C 0.16401(12) 0.70631(14) 0.45713(13) 0.0408(3) Uani 1 1 d . . . . .
H4 H 0.2083(13) 0.2755(13) 0.5108(12) 0.033(3) Uiso 1 1 d . . . . .
H3 H 0.1357(13) 0.0522(14) 0.4974(12) 0.037(3) Uiso 1 1 d . . . . .
H11 H 0.3431(13) 0.8719(14) 0.4232(12) 0.036(3) Uiso 1 1 d . . . . .
H1 H 0.0339(13) 0.0825(14) 0.8448(12) 0.037(3) Uiso 1 1 d . . . . .
H9 H 0.6346(14) 0.7091(14) 0.6319(12) 0.037(3) Uiso 1 1 d . . . . .
H12A H 0.4815(14) 0.4906(14) 0.7829(13) 0.039(4) Uiso 1 1 d . . . . .
H10 H 0.5612(14) 0.8830(15) 0.5008(12) 0.041(4) Uiso 1 1 d . . . . .
H12B H 0.4917(14) 0.4028(15) 0.6688(13) 0.045(4) Uiso 1 1 d . . . . .
H2 H 0.0464(13) -0.0467(15) 0.6729(12) 0.037(3) Uiso 1 1 d . . . . .
H13A H 0.1563(15) 0.7812(17) 0.4003(14) 0.050(4) Uiso 1 1 d . . . . .
H13B H 0.1464(17) 0.6220(19) 0.4165(16) 0.067(5) Uiso 1 1 d . . . . .
H12C H 0.6135(15) 0.4952(15) 0.7108(13) 0.047(4) Uiso 1 1 d . . . . .
H13C H 0.0993(17) 0.7164(17) 0.5209(15) 0.063(5) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C6 1.2376(12) . ?
N2 C6 1.3429(13) . ?
N2 C7 1.3330(13) . ?
N1 C5 1.3438(13) . ?
N1 C1 1.3374(15) . ?
N3 C7 1.3780(13) . ?
N3 C11 1.3648(14) . ?
N3 C13 1.4730(14) . ?
C5 C6 1.5159(14) . ?
C5 C4 1.3881(14) . ?
C7 C8 1.4323(14) . ?
C8 C9 1.3699(15) . ?
C8 C12 1.4964(15) . ?
C4 C3 1.3844(15) . ?
C4 H4 0.953(13) . ?
C2 C3 1.3815(16) . ?
C2 C1 1.3846(16) . ?
C2 H2 0.954(15) . ?
C3 H3 0.973(14) . ?
C11 C10 1.3567(16) . ?
C11 H11 0.963(14) . ?
C10 C9 1.3969(16) . ?
C10 H10 0.965(15) . ?
C1 H1 0.981(14) . ?
C9 H9 0.973(14) . ?
C12 H12A 0.971(15) . ?
C12 H12B 0.981(15) . ?
C12 H12C 0.997(16) . ?
C13 H13A 0.984(17) . ?
C13 H13B 0.970(19) . ?
C13 H13C 0.996(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
C7 N2 C6 123.15(9) . . ?
C1 N1 C5 117.02(9) . . ?
C7 N3 C13 118.55(9) . . ?
C11 N3 C7 123.15(9) . . ?
C11 N3 C13 118.30(9) . . ?
N1 C5 C6 116.68(9) . . ?
N1 C5 C4 122.31(9) . . ?
C4 C5 C6 120.94(9) . . ?
O1 C6 N2 126.78(10) . . ?
O1 C6 C5 119.49(9) . . ?
N2 C6 C5 113.70(8) . . ?
N2 C7 N3 116.63(9) . . ?
N2 C7 C8 126.27(9) . . ?
N3 C7 C8 116.70(9) . . ?
C7 C8 C12 120.21(9) . . ?
C9 C8 C7 119.13(9) . . ?
C9 C8 C12 120.54(10) . . ?
C5 C4 H4 119.6(8) . . ?
C3 C4 C5 119.64(10) . . ?
C3 C4 H4 120.8(8) . . ?
C3 C2 C1 118.03(10) . . ?
C3 C2 H2 122.2(8) . . ?
C1 C2 H2 119.7(8) . . ?
C4 C3 H3 119.1(8) . . ?
C2 C3 C4 118.53(10) . . ?
C2 C3 H3 122.3(8) . . ?
N3 C11 H11 114.9(8) . . ?
C10 C11 N3 120.43(10) . . ?
C10 C11 H11 124.7(8) . . ?
C11 C10 C9 118.67(10) . . ?
C11 C10 H10 119.6(8) . . ?
C9 C10 H10 121.7(8) . . ?
N1 C1 C2 124.41(10) . . ?
N1 C1 H1 116.8(8) . . ?
C2 C1 H1 118.7(8) . . ?
C8 C9 C10 121.88(10) . . ?
C8 C9 H9 118.5(8) . . ?
C10 C9 H9 119.6(8) . . ?
C8 C12 H12A 111.8(8) . . ?
C8 C12 H12B 111.3(9) . . ?
C8 C12 H12C 109.8(9) . . ?
H12A C12 H12B 106.0(12) . . ?
H12A C12 H12C 108.6(12) . . ?
H12B C12 H12C 109.1(12) . . ?
N3 C13 H13A 108.4(9) . . ?
N3 C13 H13B 109.6(11) . . ?
N3 C13 H13C 110.8(10) . . ?
H13A C13 H13B 109.6(13) . . ?
H13A C13 H13C 110.4(13) . . ?
H13B C13 H13C 108.0(14) . . ?

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
N2 C7 C8 C9 173.72(10) . . . . ?
N2 C7 C8 C12 -2.34(16) . . . . ?
N1 C5 C6 O1 12.07(14) . . . . ?
N1 C5 C6 N2 -166.19(9) . . . . ?
N1 C5 C4 C3 -2.40(15) . . . . ?
N3 C7 C8 C9 1.23(14) . . . . ?
N3 C7 C8 C12 -174.83(9) . . . . ?
N3 C11 C10 C9 0.99(17) . . . . ?
C5 N1 C1 C2 1.22(16) . . . . ?
C5 C4 C3 C2 1.76(16) . . . . ?
C6 N2 C7 N3 -140.11(10) . . . . ?
C6 N2 C7 C8 47.39(15) . . . . ?
C6 C5 C4 C3 174.52(9) . . . . ?
C7 N2 C6 O1 24.23(16) . . . . ?
C7 N2 C6 C5 -157.65(9) . . . . ?
C7 N3 C11 C10 -1.44(16) . . . . ?
C7 C8 C9 C10 -1.68(16) . . . . ?
C4 C5 C6 O1 -165.02(10) . . . . ?
C4 C5 C6 N2 16.72(13) . . . . ?
C3 C2 C1 N1 -1.78(17) . . . . ?
C11 N3 C7 N2 -172.94(9) . . . . ?
C11 N3 C7 C8 0.30(15) . . . . ?
C11 C10 C9 C8 0.56(17) . . . . ?
C1 N1 C5 C6 -176.13(9) . . . . ?
C1 N1 C5 C4 0.91(15) . . . . ?
C1 C2 C3 C4 0.20(16) . . . . ?
C12 C8 C9 C10 174.37(10) . . . . ?
C13 N3 C7 N2 6.88(15) . . . . ?
C13 N3 C7 C8 -179.89(10) . . . . ?
C13 N3 C11 C10 178.75(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C11 H11 O1 0.963(14) 2.194(14) 3.1540(13) 175.4(12) 4_575 yes


#----------------------------------------------------------------------------#
#                       SHELX RES FILE                                       #
#----------------------------------------------------------------------------#

####################################################################### 
# 
# 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_21MA078_ER-0186
_database_code_depnum_ccdc_archive 'CCDC 2297423'
loop_
_audit_author_name
_audit_author_address
'Simon Grabowsky'
;University of Bern
Switzerland
;
_audit_update_record             
;
2023-09-25 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C13 H13 Cl2 N3 O Pd'
_chemical_formula_sum            'C13 H13 Cl2 N3 O Pd'
_chemical_formula_weight         404.56

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_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                   13.80951(16)
_cell_length_b                   14.64287(17)
_cell_length_c                   20.4888(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4143.06(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    173.01(10)
_cell_measurement_reflns_used    15953
_cell_measurement_theta_min      4.884
_cell_measurement_theta_max      79.359

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.059
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             1600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.1311
0 1 -1 0.0923
0 -1 1 0.1089
0 0 1 0.055
0 0 -1 0.0356
6 -6 6 0.0856
-7 6 0 0.1019
7 -6 0 0.0763
-6 6 6 0.1065
-7 0 -8 0.052
7 0 8 0.0426
-9 0 0 0.0358
9 0 -1 0.0216
-6 -6 -6 0.0876
6 6 6 0.1009
-8 0 7 0.0447
-7 -6 1 0.0875
7 6 0 0.0936
-6 -6 6 0.0817
0 8 8 0.1234
0 -8 -8 0.0977

loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0008 0.9997 0.0001 -0.0852 0.0135 0.0602
-0.0004 0.9999 -0.9991 -0.1292 0.0024 0.0003
0.0004 -0.9999 0.9991 0.1292 -0.0024 -0.0003
-0.0004 -0.0003 0.9992 0.044 0.0111 0.0599
0.0004 0.0003 -0.9992 -0.044 -0.0111 -0.0599
5.6526 -6.0278 5.9666 0.7878 0.6024 -0.1283
-6.6775 6.3491 -0.059 -0.5569 -0.6443 0.5241
6.6597 -6.3701 -0.0443 0.5541 0.6409 -0.5312
-5.7665 6.0175 5.7296 -0.2718 -0.4847 0.8314
-7.3536 0.177 -7.609 -0.365 -0.8862 -0.2853
7.2723 -0.0612 7.7819 0.3625 0.8809 0.3044
-8.9612 -0.2646 0.4213 0.0233 -0.9786 0.2046
8.958 0.155 -0.627 -0.0231 0.9744 -0.2235
-5.9935 -5.9997 -6.0061 0.2347 -0.8037 -0.5906
5.9935 5.9997 6.0061 -0.2347 0.8037 0.5906
-8.0048 -0.006 6.9802 0.2922 -0.7974 0.5926
-6.9969 -6.002 0.9864 0.5411 -0.8356 -0.1496
6.9964 6.0017 0.0127 -0.497 0.8466 0.2095
-5.9989 -6.0028 5.9841 0.7633 -0.6708 0.1282
-0.0103 7.9953 7.9941 -0.3291 0.1967 0.9607
0.0103 -7.9953 -7.9941 0.3291 -0.1967 -0.9607


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    9.593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.29594
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.194
_shelx_estimated_absorpt_T_max   0.601
_oxdiff_exptl_absorpt_empirical_details 
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.712
_oxdiff_exptl_absorpt_empirical_full_min 0.535

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      173.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0019842
_diffrn_orient_matrix_ub_12      -0.0852187
_diffrn_orient_matrix_ub_13      0.0440636
_diffrn_orient_matrix_ub_21      0.1093221
_diffrn_orient_matrix_ub_22      0.0136015
_diffrn_orient_matrix_ub_23      0.0111378
_diffrn_orient_matrix_ub_31      -0.0217938
_diffrn_orient_matrix_ub_32      0.0601897
_diffrn_orient_matrix_ub_33      0.0599516
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_number            30476
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.903
_diffrn_reflns_theta_max         68.076
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             3774
_reflns_number_gt                3309
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
        List of Runs (angles in degrees, time in seconds):
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -94.00 -10.00   0.50    0.50    --  -23.00 -49.00 120.00  168
  2  ω    -36.00  50.00   0.50    0.50    --  -23.00  49.00 -92.00  172
  3  ω     35.00 120.00   0.50    0.50    --   47.70  49.00 -92.00  170
  4  ω    -24.00  52.00   0.50    0.50    --   47.70 -49.00 120.00  152
  5  ω    100.00 177.00   0.50    1.80    --  113.25  49.00 -92.00  154
  6  ω     42.00  68.00   0.50    1.80    --  113.25 -61.00 120.00   52
  7  ω     42.00 102.00   0.50    1.80    --  113.25 -77.00   0.00  120
  8  ω     42.00 106.00   0.50    1.80    --  113.25 -94.00 -60.00  128
  9  ω    101.00 177.00   0.50    1.80    --  113.25  30.00   0.00  152
 10  ω     97.00 177.00   0.50    1.80    --  113.25  61.00-180.00  160
 11  ω     25.00 120.00   0.50    0.50    --   47.70  77.00  60.00  190
 12  ω    -24.00  70.00   0.50    0.50    --   47.70 -77.00 -60.00  188
 13  ω     33.00 120.00   0.50    0.50    --   47.70  57.00   0.00  174
 14  ω     25.00 120.00   0.50    0.50    --   47.70  77.00 150.00  190
 15  ω    100.00 177.00   0.50    1.80    --  113.25  15.00 120.00  154
 16  ω     91.00 177.00   0.50    1.80    --  113.25  77.00  30.00  172
 17  ω     42.00  68.00   0.50    1.80    --  113.25 -61.00-180.00   52
 18  ω     42.00 100.00   0.50    1.80    --  113.25 -94.00 120.00  116
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0804P)²+2.0787P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3774
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.125
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.334
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.104
_olex2_refinement_description    
;
        1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
        2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C11(H11), C2(H2), C9(H9), C10(H10), C3(H3)
        2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;

#----------------------------------------------------------------------------#
#                    SQUEEZE				                                 #
#----------------------------------------------------------------------------#

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.210 0.000 0.000 365.4 63.0 ?
2 -0.291 0.000 0.500 365.4 63.0 ?
3 -0.162 0.500 0.500 365.4 63.0 ?
4 -0.437 0.500 0.000 365.4 63.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.56172(2) 0.24900(2) 0.36555(2) 0.03250(14) Uani 1 1 d . . . . .
Cl1 Cl 0.70115(6) 0.16300(6) 0.37056(4) 0.0433(2) Uani 1 1 d . . . . .
Cl2 Cl 0.57011(6) 0.25802(6) 0.25394(5) 0.0474(3) Uani 1 1 d . . . . .
N2 N 0.43813(18) 0.32084(18) 0.36905(12) 0.0362(6) Uani 1 1 d . . . . .
N1 N 0.5378(2) 0.24712(14) 0.46248(15) 0.0348(6) Uani 1 1 d . . . . .
O1 O 0.31158(17) 0.35501(18) 0.43665(12) 0.0564(6) Uani 1 1 d . . . . .
N3 N 0.3370(2) 0.31836(18) 0.27623(13) 0.0436(6) Uani 1 1 d . . . . .
C5 C 0.4517(2) 0.2847(2) 0.48051(15) 0.0388(7) Uani 1 1 d . . . . .
C7 C 0.3963(2) 0.3655(2) 0.31590(15) 0.0390(7) Uani 1 1 d . . . . .
C1 C 0.5962(2) 0.2132(2) 0.50937(15) 0.0402(7) Uani 1 1 d . . . . .
H1 H 0.656268 0.186626 0.497174 0.048 Uiso 1 1 calc R U . . .
C6 C 0.3922(2) 0.3238(2) 0.42662(15) 0.0402(7) Uani 1 1 d . . . . .
C4 C 0.4232(3) 0.2881(2) 0.54470(17) 0.0474(8) Uani 1 1 d . . . . .
H4 H 0.36261 0.314165 0.556217 0.057 Uiso 1 1 calc R U . . .
C11 C 0.2974(3) 0.3567(2) 0.22231(18) 0.0524(8) Uani 1 1 d . . . . .
H11 H 0.257507 0.321304 0.194272 0.063 Uiso 1 1 calc R U . . .
C2 C 0.5713(3) 0.2161(2) 0.57428(17) 0.0469(8) Uani 1 1 d . . . . .
H2 H 0.614288 0.192624 0.606367 0.056 Uiso 1 1 calc R U . . .
C8 C 0.4164(3) 0.4574(2) 0.30261(17) 0.0497(8) Uani 1 1 d . . . . .
C9 C 0.3737(3) 0.4963(2) 0.24885(19) 0.0551(9) Uani 1 1 d . . . . .
H9 H 0.385091 0.55901 0.239603 0.066 Uiso 1 1 calc R U . . .
C13 C 0.3172(3) 0.2213(2) 0.2905(2) 0.0526(9) Uani 1 1 d . . . . .
H13A H 0.377637 0.186454 0.28806 0.079 Uiso 1 1 calc R U . . .
H13B H 0.270979 0.197303 0.258516 0.079 Uiso 1 1 calc R U . . .
H13C H 0.289746 0.215784 0.334452 0.079 Uiso 1 1 calc R U . . .
C10 C 0.3152(3) 0.4465(2) 0.20831(18) 0.0548(9) Uani 1 1 d . . . . .
H10 H 0.287152 0.474098 0.170828 0.066 Uiso 1 1 calc R U . . .
C3 C 0.4839(3) 0.2531(2) 0.59258(19) 0.0509(9) Uani 1 1 d . . . . .
H3 H 0.465303 0.254689 0.637213 0.061 Uiso 1 1 calc R U . . .
C12 C 0.4832(4) 0.5092(3) 0.3458(2) 0.0799(15) Uani 1 1 d . . . . .
H12A H 0.45909 0.507171 0.390765 0.12 Uiso 1 1 calc R U . . .
H12B H 0.486766 0.57278 0.331148 0.12 Uiso 1 1 calc R U . . .
H12C H 0.54785 0.481655 0.343975 0.12 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.3029(8) . ?
Pd1 Cl2 2.2935(11) . ?
Pd1 N2 2.006(3) . ?
Pd1 N1 2.013(3) . ?
N2 C7 1.396(4) . ?
N2 C6 1.340(4) . ?
N1 C5 1.362(4) . ?
N1 C1 1.348(4) . ?
O1 C6 1.221(4) . ?
N3 C7 1.344(4) . ?
N3 C11 1.354(4) . ?
N3 C13 1.476(4) . ?
C5 C6 1.490(4) . ?
C5 C4 1.374(4) . ?
C7 C8 1.401(4) . ?
C1 H1 0.95 . ?
C1 C2 1.374(5) . ?
C4 H4 0.95 . ?
C4 C3 1.388(5) . ?
C11 H11 0.95 . ?
C11 C10 1.369(5) . ?
C2 H2 0.95 . ?
C2 C3 1.376(6) . ?
C8 C9 1.373(5) . ?
C8 C12 1.487(5) . ?
C9 H9 0.95 . ?
C9 C10 1.370(5) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C10 H10 0.95 . ?
C3 H3 0.95 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?

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 91.94(3) . . ?
N2 Pd1 Cl1 175.14(8) . . ?
N2 Pd1 Cl2 92.78(7) . . ?
N2 Pd1 N1 80.36(11) . . ?
N1 Pd1 Cl1 94.90(8) . . ?
N1 Pd1 Cl2 173.01(9) . . ?
C7 N2 Pd1 124.7(2) . . ?
C6 N2 Pd1 116.8(2) . . ?
C6 N2 C7 118.4(3) . . ?
C5 N1 Pd1 113.9(2) . . ?
C1 N1 Pd1 127.6(2) . . ?
C1 N1 C5 118.5(3) . . ?
C7 N3 C11 121.7(3) . . ?
C7 N3 C13 119.2(3) . . ?
C11 N3 C13 119.1(3) . . ?
N1 C5 C6 115.8(3) . . ?
N1 C5 C4 121.6(3) . . ?
C4 C5 C6 122.5(3) . . ?
N2 C7 C8 121.3(3) . . ?
N3 C7 N2 118.9(3) . . ?
N3 C7 C8 119.8(3) . . ?
N1 C1 H1 119 . . ?
N1 C1 C2 121.9(3) . . ?
C2 C1 H1 119 . . ?
N2 C6 C5 112.2(3) . . ?
O1 C6 N2 126.3(3) . . ?
O1 C6 C5 121.5(3) . . ?
C5 C4 H4 120.3 . . ?
C5 C4 C3 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
N3 C11 H11 120.1 . . ?
N3 C11 C10 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C7 C8 C12 119.8(3) . . ?
C9 C8 C7 118.1(3) . . ?
C9 C8 C12 122.1(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C4 C3 H3 120.6 . . ?
C2 C3 C4 118.8(4) . . ?
C2 C3 H3 120.6 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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 N2 C7 N3 86.2(3) . . . . ?
Pd1 N2 C7 C8 -92.6(3) . . . . ?
Pd1 N2 C6 O1 -171.3(3) . . . . ?
Pd1 N2 C6 C5 9.5(3) . . . . ?
Pd1 N1 C5 C6 -2.3(3) . . . . ?
Pd1 N1 C5 C4 179.2(3) . . . . ?
Pd1 N1 C1 C2 -179.9(2) . . . . ?
N2 C7 C8 C9 179.0(3) . . . . ?
N2 C7 C8 C12 -0.2(6) . . . . ?
N1 C5 C6 N2 -4.6(4) . . . . ?
N1 C5 C6 O1 176.2(3) . . . . ?
N1 C5 C4 C3 0.5(5) . . . . ?
N1 C1 C2 C3 1.0(5) . . . . ?
N3 C7 C8 C9 0.2(5) . . . . ?
N3 C7 C8 C12 -179.0(4) . . . . ?
N3 C11 C10 C9 0.7(6) . . . . ?
C5 N1 C1 C2 -0.3(4) . . . . ?
C5 C4 C3 C2 0.2(5) . . . . ?
C7 N2 C6 O1 7.2(5) . . . . ?
C7 N2 C6 C5 -171.9(3) . . . . ?
C7 N3 C11 C10 -2.1(5) . . . . ?
C7 C8 C9 C10 -1.6(6) . . . . ?
C1 N1 C5 C6 178.0(3) . . . . ?
C1 N1 C5 C4 -0.5(4) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
C6 N2 C7 N3 -92.2(4) . . . . ?
C6 N2 C7 C8 89.0(4) . . . . ?
C6 C5 C4 C3 -177.8(3) . . . . ?
C4 C5 C6 N2 173.9(3) . . . . ?
C4 C5 C6 O1 -5.3(5) . . . . ?
C11 N3 C7 N2 -177.1(3) . . . . ?
C11 N3 C7 C8 1.7(5) . . . . ?
C8 C9 C10 C11 1.2(6) . . . . ?
C13 N3 C7 N2 0.7(4) . . . . ?
C13 N3 C7 C8 179.5(3) . . . . ?
C13 N3 C11 C10 -179.9(3) . . . . ?
C12 C8 C9 C10 177.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 Cl1 0.95 2.69 3.276(3) 120.5 . yes
C4 H4 Cl1 0.95 2.71 3.596(3) 155.9 4_456 yes
C11 H11 Cl1 0.95 2.78 3.665(4) 154.9 6_556 yes


#----------------------------------------------------------------------------#
#                       SHELX RES FILE                                       #
#----------------------------------------------------------------------------#


# END of CIF
####################################################################### 
# 
# 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_22MA091_ER-0397
_database_code_depnum_ccdc_archive 'CCDC 2297427'
loop_
_audit_author_name
_audit_author_address
'Simon Grabowsky'
;University of Bern
Switzerland
;
_audit_update_record             
;
2023-09-25 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;

_audit_creation_date             2022-09-08T18:48:41-00:00

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C13 H15 Cl2 N3 Pd'
_chemical_formula_sum            'C13 H15 Cl2 N3 Pd'
_chemical_formula_weight         390.58

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.85526(8)
_cell_length_b                   13.58959(9)
_cell_length_c                   11.48119(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.9973(8)
_cell_angle_gamma                90
_cell_volume                     1462.43(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173.01(10)
_cell_measurement_reflns_used    24412
_cell_measurement_theta_min      4.131
_cell_measurement_theta_max      79.838

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_F_000             776
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.1311
1 1 -1 0.0898
-1 -1 1 0.0862
1 0 -1 0.0824
-1 0 1 0.09
1 1 0 0.0445
-1 -1 0 0.0459
1 -1 -1 0.0801
-1 1 1 0.0816
-1 -1 -1 0.1178
-1 0 0 0.0497
1 1 1 0.1152
1 -1 0 0.0453
-1 1 0 0.0431
0 1 0 0.0471
0 -1 0 0.0471
0 -1 1 0.1239
5 5 -2 0.0298
6 -1 -1 0.0204
-6 2 1 0.0332


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    13.506
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
        Numerical absorption correction based on gaussian integration over
        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.099
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.097
_shelx_estimated_absorpt_T_max   0.498

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      173.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.1043388
_diffrn_orient_matrix_ub_12      -0.0376443
_diffrn_orient_matrix_ub_13      0.0659321
_diffrn_orient_matrix_ub_21      -0.1183472
_diffrn_orient_matrix_ub_22      0.0657438
_diffrn_orient_matrix_ub_23      -0.0823201
_diffrn_orient_matrix_ub_31      -0.0458939
_diffrn_orient_matrix_ub_32      -0.0843933
_diffrn_orient_matrix_ub_33      -0.0936869
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_number            29939
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.718
_diffrn_reflns_theta_max         79.968
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             3184
_reflns_number_gt                3165
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+1.9810P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.00027(8)
_refine_ls_number_reflns         3184
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.951
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.111

#----------------------------------------------------------------------------#
#                   SQUEEZE                                                  #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.30846(2) 0.22364(2) 0.38905(2) 0.02417(10) Uani 1 1 d . . . . .
Cl2 Cl 0.09696(8) 0.23776(6) 0.43211(8) 0.03549(18) Uani 1 1 d . . . . .
Cl1 Cl 0.31840(8) 0.05528(5) 0.42334(8) 0.03502(17) Uani 1 1 d . . . . .
N1 N 0.4861(3) 0.22764(17) 0.3365(2) 0.0269(5) Uani 1 1 d . . . . .
N2 N 0.3118(3) 0.36649(17) 0.3431(2) 0.0288(5) Uani 1 1 d . . . . .
N3 N 0.1145(3) 0.4806(2) 0.2760(3) 0.0379(6) Uani 1 1 d . . . . .
C8 C 0.2546(3) 0.4689(2) 0.4871(3) 0.0310(6) Uani 1 1 d . . . . .
C5 C 0.4872(3) 0.3042(2) 0.2607(3) 0.0304(6) Uani 1 1 d . . . . .
C7 C 0.2272(3) 0.4365(2) 0.3655(3) 0.0277(5) Uani 1 1 d . . . . .
C1 C 0.5980(3) 0.1663(2) 0.3700(3) 0.0338(6) Uani 1 1 d . . . . .
H1 H 0.59644 0.112692 0.422718 0.041 Uiso 1 1 calc R U . . .
C6 C 0.3565(3) 0.3684(2) 0.2321(3) 0.0318(6) Uani 1 1 d . . . . .
H6A H 0.379251 0.436446 0.213398 0.038 Uiso 1 1 calc R U . . .
H6B H 0.280144 0.34227 0.160955 0.038 Uiso 1 1 calc R U . . .
C2 C 0.7154(4) 0.1789(3) 0.3301(3) 0.0426(8) Uani 1 1 d . . . . .
H2 H 0.794932 0.135841 0.357214 0.051 Uiso 1 1 calc R U . . .
C4 C 0.5993(4) 0.3185(2) 0.2143(3) 0.0371(7) Uani 1 1 d . . . . .
H4 H 0.596851 0.370984 0.15901 0.045 Uiso 1 1 calc R U . . .
C3 C 0.7158(4) 0.2555(3) 0.2495(4) 0.0433(8) Uani 1 1 d . . . . .
H3 H 0.794344 0.264416 0.219178 0.052 Uiso 1 1 calc R U . . .
C12 C 0.0583(4) 0.4362(3) 0.1528(3) 0.0450(8) Uani 1 1 d . . . . .
H12A H 0.119748 0.454507 0.10351 0.067 Uiso 1 1 calc R U . . .
H12B H -0.038707 0.460342 0.112935 0.067 Uiso 1 1 calc R U . . .
H12C H 0.056609 0.364436 0.160288 0.067 Uiso 1 1 calc R U . . .
C11 C 0.0427(4) 0.5594(3) 0.3041(4) 0.0478(9) Uani 1 1 d . . . . .
H11 H -0.031081 0.590359 0.241124 0.057 Uiso 1 1 calc R U . . .
C9 C 0.1788(5) 0.5462(3) 0.5125(4) 0.0481(9) Uani 1 1 d . . . . .
H9 H 0.197584 0.567439 0.59477 0.058 Uiso 1 1 calc R U . . .
C10 C 0.0759(5) 0.5935(3) 0.4206(5) 0.0567(11) Uani 1 1 d . . . . .
H10 H 0.02855 0.649683 0.438618 0.068 Uiso 1 1 calc R U . . .
C13 C 0.3691(5) 0.4212(3) 0.5862(3) 0.0512(9) Uani 1 1 d . . . . .
H13A H 0.34512 0.351822 0.592492 0.077 Uiso 1 1 calc R U . . .
H13B H 0.378617 0.454456 0.664011 0.077 Uiso 1 1 calc R U . . .
H13C H 0.459484 0.425724 0.567502 0.077 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 Cl2 2.2940(8) . ?
Pd1 Cl1 2.3186(7) . ?
Pd1 N1 2.021(3) . ?
Pd1 N2 2.015(2) . ?
N1 C5 1.359(4) . ?
N1 C1 1.340(4) . ?
N2 C7 1.341(4) . ?
N2 C6 1.472(4) . ?
N3 C7 1.394(4) . ?
N3 C12 1.479(5) . ?
N3 C11 1.376(4) . ?
C8 C7 1.409(4) . ?
C8 C9 1.372(5) . ?
C8 C13 1.481(5) . ?
C5 C6 1.506(4) . ?
C5 C4 1.380(4) . ?
C1 H1 0.95 . ?
C1 C2 1.381(5) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C2 H2 0.95 . ?
C2 C3 1.394(6) . ?
C4 H4 0.95 . ?
C4 C3 1.389(5) . ?
C3 H3 0.95 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C11 H11 0.95 . ?
C11 C10 1.357(6) . ?
C9 H9 0.95 . ?
C9 C10 1.376(6) . ?
C10 H10 0.95 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?

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 92.26(3) . . ?
N1 Pd1 Cl2 172.15(7) . . ?
N1 Pd1 Cl1 94.71(7) . . ?
N2 Pd1 Cl2 93.74(7) . . ?
N2 Pd1 Cl1 172.80(7) . . ?
N2 Pd1 N1 79.06(10) . . ?
C5 N1 Pd1 113.03(19) . . ?
C1 N1 Pd1 127.5(2) . . ?
C1 N1 C5 119.4(3) . . ?
C7 N2 Pd1 124.92(19) . . ?
C7 N2 C6 121.6(2) . . ?
C6 N2 Pd1 106.12(17) . . ?
C7 N3 C12 120.5(3) . . ?
C11 N3 C7 120.8(3) . . ?
C11 N3 C12 118.3(3) . . ?
C7 C8 C13 119.4(3) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 C13 120.6(3) . . ?
N1 C5 C6 114.0(3) . . ?
N1 C5 C4 121.4(3) . . ?
C4 C5 C6 124.5(3) . . ?
N2 C7 N3 124.3(3) . . ?
N2 C7 C8 118.2(3) . . ?
N3 C7 C8 117.5(3) . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.8(3) . . ?
C2 C1 H1 119.1 . . ?
N2 C6 C5 105.4(2) . . ?
N2 C6 H6A 110.7 . . ?
N2 C6 H6B 110.7 . . ?
C5 C6 H6A 110.7 . . ?
C5 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C5 C4 H4 120.4 . . ?
C5 C4 C3 119.3(3) . . ?
C3 C4 H4 120.4 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C11 H11 119.6 . . ?
C10 C11 N3 120.8(4) . . ?
C10 C11 H11 119.6 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 121.1(3) . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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 N1 C5 C6 -0.3(3) . . . . ?
Pd1 N1 C5 C4 -179.4(2) . . . . ?
Pd1 N1 C1 C2 -178.0(2) . . . . ?
Pd1 N2 C7 N3 -108.1(3) . . . . ?
Pd1 N2 C7 C8 72.6(3) . . . . ?
Pd1 N2 C6 C5 -49.0(3) . . . . ?
N1 C5 C6 N2 32.7(3) . . . . ?
N1 C5 C4 C3 -2.4(5) . . . . ?
N1 C1 C2 C3 -2.1(5) . . . . ?
N3 C11 C10 C9 -2.6(6) . . . . ?
C8 C9 C10 C11 4.1(6) . . . . ?
C5 N1 C1 C2 0.3(5) . . . . ?
C5 C4 C3 C2 0.5(5) . . . . ?
C7 N2 C6 C5 159.7(3) . . . . ?
C7 N3 C11 C10 -2.8(5) . . . . ?
C7 C8 C9 C10 -0.2(5) . . . . ?
C1 N1 C5 C6 -178.9(3) . . . . ?
C1 N1 C5 C4 2.0(4) . . . . ?
C1 C2 C3 C4 1.7(6) . . . . ?
C6 N2 C7 N3 37.6(4) . . . . ?
C6 N2 C7 C8 -141.7(3) . . . . ?
C6 C5 C4 C3 178.6(3) . . . . ?
C4 C5 C6 N2 -148.2(3) . . . . ?
C12 N3 C7 N2 14.7(5) . . . . ?
C12 N3 C7 C8 -166.0(3) . . . . ?
C12 N3 C11 C10 169.9(4) . . . . ?
C11 N3 C7 N2 -172.8(3) . . . . ?
C11 N3 C7 C8 6.5(4) . . . . ?
C9 C8 C7 N2 174.3(3) . . . . ?
C9 C8 C7 N3 -5.0(4) . . . . ?
C13 C8 C7 N2 -3.4(5) . . . . ?
C13 C8 C7 N3 177.3(3) . . . . ?
C13 C8 C9 C10 177.4(4) . . . . ?


#----------------------------------------------------------------------------#
#                   SHELX RES FILE                                           #
#----------------------------------------------------------------------------#

####################################################################### 
# 
# 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_22MA068_ER-0491
_database_code_depnum_ccdc_archive 'CCDC 2297426'
loop_
_audit_author_name
_audit_author_address
'Simon Grabowsky'
;University of Bern
Switzerland
;
_audit_update_record             
;
2023-09-25 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;

_audit_creation_date             2022-07-12T19:40:30-00:00

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C21 H21 Cl2 N3 O Pd'
_chemical_formula_sum            'C21 H21 Cl2 N3 O Pd'
_chemical_formula_weight         508.71

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   30.25121(18)
_cell_length_b                   9.45051(5)
_cell_length_c                   14.29074(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.7911(5)
_cell_angle_gamma                90
_cell_volume                     4076.63(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173.01(10)
_cell_measurement_reflns_used    34492
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      31.428

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.073
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_F_000             2048
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 1 0.0816
-1 1 -1 0.0925
-1 0 1 0.0394
-1 0 0 0.0429
1 0 0 0.0297
-1 -1 1 0.0734
14 -3 18 0.0345
-1 0 -1 0.084
-13 3 -18 0.0792
1 1 0 0.1212
-1 -1 0 0.0947
0 1 -1 0.0919
-1 -1 -1 0.0902
1 1 1 0.1197
0 -1 1 0.0779
0 -1 -1 0.0852
0 1 1 0.118
0 1 0 0.1205
0 0 1 0.0355
0 0 -1 0.0968
-1 7 -17 0.0838
0 -5 18 0.045


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.19
_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_correction_T_min  0.83187
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.781
_shelx_estimated_absorpt_T_max   0.918

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      173.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0965
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0182006
_diffrn_orient_matrix_ub_12      -0.0423004
_diffrn_orient_matrix_ub_13      -0.0167847
_diffrn_orient_matrix_ub_21      0.0146176
_diffrn_orient_matrix_ub_22      -0.0448344
_diffrn_orient_matrix_ub_23      -0.0230899
_diffrn_orient_matrix_ub_31      0.0026771
_diffrn_orient_matrix_ub_32      -0.0428088
_diffrn_orient_matrix_ub_33      0.0407452
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_number            55339
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.258
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             5712
_reflns_number_gt                5453
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0216P)²+5.7574P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5712
_refine_ls_number_parameters     258
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.054
_refine_ls_wR_factor_gt          0.0533
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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 0.37375(2) 0.13025(2) 0.71726(2) 0.01596(4) Uani 1 1 d . . . . .
Cl1 Cl 0.33444(2) -0.07441(4) 0.73643(3) 0.02441(8) Uani 1 1 d . . . . .
Cl2 Cl 0.42996(2) 0.00293(4) 0.66074(3) 0.02561(8) Uani 1 1 d . . . . .
N3 N 0.39777(4) 0.33181(13) 0.69455(9) 0.0175(2) Uani 1 1 d . . . . .
O1 O 0.32773(5) 0.45557(14) 0.86871(10) 0.0348(3) Uani 1 1 d . . . . .
N2 N 0.33223(5) 0.24267(14) 0.79296(9) 0.0211(3) Uani 1 1 d . . . . .
N1 N 0.30999(5) 0.14412(16) 0.93730(10) 0.0251(3) Uani 0.617(17) 1 d . U P A 1
C9 C 0.38046(5) 0.42764(16) 0.75369(11) 0.0201(3) Uani 1 1 d . . . . .
C2 C 0.25800(5) 0.16020(17) 0.80418(11) 0.0253(3) Uani 0.617(17) 1 d . U P A 1
C13 C 0.42572(5) 0.37927(16) 0.63189(11) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.34444(6) 0.37680(16) 0.81260(11) 0.0221(3) Uani 1 1 d . . . . .
C1 C 0.29990(5) 0.18328(16) 0.84568(11) 0.0207(3) Uani 1 1 d . U . . .
C16 C 0.42502(6) 0.16072(19) 0.41142(11) 0.0271(3) Uani 1 1 d . . . . .
H16 H 0.404311 0.126175 0.363985 0.033 Uiso 1 1 calc R U . . .
C19 C 0.48638(6) 0.26116(18) 0.54952(11) 0.0243(3) Uani 1 1 d . . . . .
C15 C 0.40987(6) 0.23649(17) 0.48648(11) 0.0227(3) Uani 1 1 d . . . . .
C14 C 0.44100(5) 0.28733(16) 0.55560(10) 0.0199(3) Uani 1 1 d . . . . .
C18 C 0.49997(6) 0.18431(19) 0.47383(12) 0.0273(3) Uani 1 1 d . . . . .
H18 H 0.530595 0.165312 0.469396 0.033 Uiso 1 1 calc R U . . .
C10 C 0.39264(6) 0.56753(17) 0.75674(12) 0.0263(3) Uani 1 1 d . . . . .
H10 H 0.380286 0.630306 0.799896 0.032 Uiso 1 1 calc R U . . .
C12 C 0.43889(6) 0.52159(18) 0.63277(13) 0.0290(4) Uani 1 1 d . . . . .
H12 H 0.45899 0.553255 0.588899 0.035 Uiso 1 1 calc R U . . .
C17 C 0.46969(7) 0.13490(18) 0.40475(12) 0.0286(4) Uani 1 1 d . . . . .
H17 H 0.479536 0.083442 0.352936 0.034 Uiso 1 1 calc R U . . .
C6 C 0.35569(7) 0.1641(2) 0.98033(13) 0.0352(4) Uani 1 1 d . . . . .
H6AA H 0.377068 0.125262 0.938581 0.053 Uiso 0.617(17) 1 calc R U P A 1
H6AB H 0.358673 0.11502 1.040815 0.053 Uiso 0.617(17) 1 calc R U P A 1
H6AC H 0.361429 0.265331 0.989956 0.053 Uiso 0.617(17) 1 calc R U P A 1
H6BD H 0.376519 0.108731 0.945513 0.053 Uiso 0.383(17) 1 calc R U P A 2
H6BE H 0.357005 0.132332 1.045728 0.053 Uiso 0.383(17) 1 calc R U P A 2
H6BF H 0.363647 0.264549 0.978111 0.053 Uiso 0.383(17) 1 calc R U P A 2
C7 C 0.24822(6) 0.1985(2) 0.70382(13) 0.0324(4) Uani 1 1 d . . . . .
H7BD H 0.240175 0.298784 0.69913 0.049 Uiso 0.383(17) 1 calc R U P A 2
H7BE H 0.223555 0.140681 0.677401 0.049 Uiso 0.383(17) 1 calc R U P A 2
H7BF H 0.274505 0.18111 0.668911 0.049 Uiso 0.383(17) 1 calc R U P A 2
H7AA H 0.253417 0.299876 0.695332 0.049 Uiso 0.617(17) 1 calc R U P A 1
H7AB H 0.217215 0.176383 0.685344 0.049 Uiso 0.617(17) 1 calc R U P A 1
H7AC H 0.267603 0.144315 0.664767 0.049 Uiso 0.617(17) 1 calc R U P A 1
C5 C 0.27824(7) 0.0849(2) 0.98873(13) 0.0332(3) Uani 1 1 d . U . . .
H5A H 0.285389 0.058184 1.052004 0.04 Uiso 0.617(17) 1 calc R U P A 1
H5B H 0.285389 0.058184 1.052004 0.04 Uiso 0.383(17) 1 calc R U P A 2
C11 C 0.42329(7) 0.61631(18) 0.69593(14) 0.0314(4) Uani 1 1 d . . . . .
H11 H 0.433126 0.711796 0.6979 0.038 Uiso 1 1 calc R U . . .
C3 C 0.22620(6) 0.1012(2) 0.85717(15) 0.0348(4) Uani 1 1 d . U . . .
H3B H 0.197131 0.086134 0.829647 0.042 Uiso 0.383(17) 1 calc R U P A 2
H3A H 0.197131 0.086134 0.829647 0.042 Uiso 0.617(17) 1 calc R U P A 1
C20 C 0.36074(6) 0.2606(2) 0.49069(12) 0.0314(4) Uani 1 1 d . . . . .
H20A H 0.345497 0.233522 0.430719 0.047 Uiso 1 1 calc R U . . .
H20B H 0.355214 0.360896 0.502959 0.047 Uiso 1 1 calc R U . . .
H20C H 0.349588 0.20315 0.54112 0.047 Uiso 1 1 calc R U . . .
C4 C 0.23604(7) 0.0639(2) 0.94947(15) 0.0393(4) Uani 1 1 d . U . . .
H4 H 0.213886 0.024028 0.985554 0.047 Uiso 1 1 calc R U . . .
C21 C 0.52106(6) 0.3033(3) 0.62518(14) 0.0409(5) Uani 1 1 d . . . . .
H21A H 0.51925 0.405366 0.636415 0.061 Uiso 1 1 calc R U . . .
H21B H 0.550532 0.279725 0.60514 0.061 Uiso 1 1 calc R U . . .
H21C H 0.515908 0.252155 0.683117 0.061 Uiso 1 1 calc R U . . .
N1A N 0.25800(5) 0.16020(17) 0.80418(11) 0.0253(3) Uani 0.383(17) 1 d . U P A 2
C2A C 0.30999(5) 0.14412(16) 0.93730(10) 0.0251(3) Uani 0.383(17) 1 d . U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.2964(4) . ?
Pd1 Cl2 2.2745(4) . ?
Pd1 N3 2.0719(13) . ?
Pd1 N2 2.0142(13) . ?
N3 C9 1.3664(19) . ?
N3 C13 1.3485(19) . ?
O1 C8 1.2272(19) . ?
N2 C8 1.345(2) . ?
N2 C1 1.3914(19) . ?
N1 C1 1.375(2) . ?
N1 C6 1.488(2) . ?
N1 C5 1.367(2) . ?
C9 C8 1.500(2) . ?
C9 C10 1.372(2) . ?
C2 C1 1.381(2) . ?
C2 C7 1.490(2) . ?
C2 C3 1.381(2) . ?
C13 C14 1.491(2) . ?
C13 C12 1.403(2) . ?
C1 N1A 1.381(2) . ?
C1 C2A 1.375(2) . ?
C16 H16 0.95 . ?
C16 C15 1.392(2) . ?
C16 C17 1.383(3) . ?
C19 C14 1.403(2) . ?
C19 C18 1.387(2) . ?
C19 C21 1.509(2) . ?
C15 C14 1.404(2) . ?
C15 C20 1.509(2) . ?
C18 H18 0.95 . ?
C18 C17 1.383(3) . ?
C10 H10 0.95 . ?
C10 C11 1.391(2) . ?
C12 H12 0.95 . ?
C12 C11 1.377(2) . ?
C17 H17 0.95 . ?
C6 H6AA 0.98 . ?
C6 H6AB 0.98 . ?
C6 H6AC 0.98 . ?
C6 H6BD 0.98 . ?
C6 H6BE 0.98 . ?
C6 H6BF 0.98 . ?
C6 C2A 1.488(2) . ?
C7 H7BD 0.98 . ?
C7 H7BE 0.98 . ?
C7 H7BF 0.98 . ?
C7 H7AA 0.98 . ?
C7 H7AB 0.98 . ?
C7 H7AC 0.98 . ?
C7 N1A 1.490(2) . ?
C5 H5A 0.95 . ?
C5 H5B 0.95 . ?
C5 C4 1.375(3) . ?
C5 C2A 1.367(2) . ?
C11 H11 0.95 . ?
C3 H3B 0.95 . ?
C3 H3A 0.95 . ?
C3 C4 1.379(3) . ?
C3 N1A 1.381(2) . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C4 H4 0.95 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?

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 90.117(15) . . ?
N3 Pd1 Cl1 169.34(4) . . ?
N3 Pd1 Cl2 98.78(4) . . ?
N2 Pd1 Cl1 91.94(4) . . ?
N2 Pd1 Cl2 167.75(4) . . ?
N2 Pd1 N3 80.61(5) . . ?
C9 N3 Pd1 111.09(10) . . ?
C13 N3 Pd1 130.66(10) . . ?
C13 N3 C9 118.23(13) . . ?
C8 N2 Pd1 115.90(11) . . ?
C8 N2 C1 117.42(13) . . ?
C1 N2 Pd1 124.30(10) . . ?
C1 N1 C6 120.06(15) . . ?
C5 N1 C1 120.16(16) . . ?
C5 N1 C6 119.77(16) . . ?
N3 C9 C8 117.21(13) . . ?
N3 C9 C10 123.04(15) . . ?
C10 C9 C8 119.63(14) . . ?
C1 C2 C7 119.56(15) . . ?
C3 C2 C1 118.78(16) . . ?
C3 C2 C7 121.66(16) . . ?
N3 C13 C14 122.00(13) . . ?
N3 C13 C12 120.22(14) . . ?
C12 C13 C14 117.63(14) . . ?
O1 C8 N2 126.07(16) . . ?
O1 C8 C9 121.23(14) . . ?
N2 C8 C9 112.63(13) . . ?
N1 C1 N2 120.29(15) . . ?
N1 C1 C2 120.39(15) . . ?
C2 C1 N2 119.29(14) . . ?
N1A C1 N2 119.29(14) . . ?
C2A C1 N2 120.29(15) . . ?
C2A C1 N1A 120.39(15) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C17 C16 C15 121.13(16) . . ?
C14 C19 C21 123.06(15) . . ?
C18 C19 C14 118.82(15) . . ?
C18 C19 C21 117.96(16) . . ?
C16 C15 C14 118.59(15) . . ?
C16 C15 C20 118.93(15) . . ?
C14 C15 C20 122.48(15) . . ?
C19 C14 C13 119.98(14) . . ?
C19 C14 C15 120.64(14) . . ?
C15 C14 C13 119.21(14) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 C19 121.13(16) . . ?
C17 C18 H18 119.4 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.22(15) . . ?
C11 C10 H10 120.4 . . ?
C13 C12 H12 119.3 . . ?
C11 C12 C13 121.32(16) . . ?
C11 C12 H12 119.3 . . ?
C16 C17 C18 119.69(16) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
N1 C6 H6AA 109.5 . . ?
N1 C6 H6AB 109.5 . . ?
N1 C6 H6AC 109.5 . . ?
H6AA C6 H6AB 109.5 . . ?
H6AA C6 H6AC 109.5 . . ?
H6AB C6 H6AC 109.5 . . ?
H6BD C6 H6BE 109.5 . . ?
H6BD C6 H6BF 109.5 . . ?
H6BE C6 H6BF 109.5 . . ?
C2A C6 H6BD 109.5 . . ?
C2A C6 H6BE 109.5 . . ?
C2A C6 H6BF 109.5 . . ?
C2 C7 H7AA 109.5 . . ?
C2 C7 H7AB 109.5 . . ?
C2 C7 H7AC 109.5 . . ?
H7BD C7 H7BE 109.5 . . ?
H7BD C7 H7BF 109.5 . . ?
H7BE C7 H7BF 109.5 . . ?
H7AA C7 H7AB 109.5 . . ?
H7AA C7 H7AC 109.5 . . ?
H7AB C7 H7AC 109.5 . . ?
N1A C7 H7BD 109.5 . . ?
N1A C7 H7BE 109.5 . . ?
N1A C7 H7BF 109.5 . . ?
N1 C5 H5A 119.8 . . ?
N1 C5 C4 120.42(18) . . ?
C4 C5 H5A 119.8 . . ?
C4 C5 H5B 119.8 . . ?
C2A C5 H5B 119.8 . . ?
C2A C5 C4 120.42(18) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 C10 117.77(15) . . ?
C12 C11 H11 121.1 . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 C2 120.92(18) . . ?
C4 C3 H3B 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C4 C3 N1A 120.92(18) . . ?
N1A C3 H3B 119.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C5 C4 C3 119.30(17) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1A C7 119.56(15) . . ?
C3 N1A C1 118.78(16) . . ?
C3 N1A C7 121.66(16) . . ?
C1 C2A C6 120.06(15) . . ?
C5 C2A C1 120.16(16) . . ?
C5 C2A C6 119.77(16) . . ?

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 C9 C8 -7.62(17) . . . . ?
Pd1 N3 C9 C10 176.48(13) . . . . ?
Pd1 N3 C13 C14 7.6(2) . . . . ?
Pd1 N3 C13 C12 -177.06(13) . . . . ?
Pd1 N2 C8 O1 -168.35(15) . . . . ?
Pd1 N2 C8 C9 14.79(18) . . . . ?
Pd1 N2 C1 N1 88.25(17) . . . . ?
Pd1 N2 C1 C2 -89.82(17) . . . . ?
Pd1 N2 C1 N1A -89.82(17) . . . . ?
Pd1 N2 C1 C2A 88.25(17) . . . . ?
N3 C9 C8 O1 178.66(16) . . . . ?
N3 C9 C8 N2 -4.3(2) . . . . ?
N3 C9 C10 C11 1.4(3) . . . . ?
N3 C13 C14 C19 -120.86(17) . . . . ?
N3 C13 C14 C15 63.9(2) . . . . ?
N3 C13 C12 C11 -1.0(3) . . . . ?
N2 C1 N1A C7 0.3(2) . . . . ?
N2 C1 N1A C3 180.00(15) . . . . ?
N2 C1 C2A C6 -0.5(2) . . . . ?
N2 C1 C2A C5 -179.57(15) . . . . ?
N1 C5 C4 C3 0.9(3) . . . . ?
C9 N3 C13 C14 -170.85(14) . . . . ?
C9 N3 C13 C12 4.5(2) . . . . ?
C9 C10 C11 C12 2.2(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C13 N3 C9 C8 171.08(14) . . . . ?
C13 N3 C9 C10 -4.8(2) . . . . ?
C13 C12 C11 C10 -2.4(3) . . . . ?
C8 N2 C1 N1 -73.5(2) . . . . ?
C8 N2 C1 C2 108.45(18) . . . . ?
C8 N2 C1 N1A 108.45(18) . . . . ?
C8 N2 C1 C2A -73.5(2) . . . . ?
C8 C9 C10 C11 -174.41(17) . . . . ?
C1 N2 C8 O1 -5.1(3) . . . . ?
C1 N2 C8 C9 178.06(14) . . . . ?
C1 N1 C5 C4 0.1(3) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C16 C15 C14 C13 174.69(14) . . . . ?
C16 C15 C14 C19 -0.6(2) . . . . ?
C19 C18 C17 C16 -0.8(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C14 C13 C12 C11 174.55(17) . . . . ?
C14 C19 C18 C17 0.6(3) . . . . ?
C18 C19 C14 C13 -175.10(15) . . . . ?
C18 C19 C14 C15 0.1(2) . . . . ?
C10 C9 C8 O1 -5.3(3) . . . . ?
C10 C9 C8 N2 171.73(15) . . . . ?
C12 C13 C14 C19 63.6(2) . . . . ?
C12 C13 C14 C15 -111.64(18) . . . . ?
C17 C16 C15 C14 0.3(2) . . . . ?
C17 C16 C15 C20 -179.52(16) . . . . ?
C6 N1 C1 N2 -0.5(2) . . . . ?
C6 N1 C1 C2 177.59(16) . . . . ?
C6 N1 C5 C4 -179.05(18) . . . . ?
C7 C2 C1 N2 0.3(2) . . . . ?
C7 C2 C1 N1 -177.74(15) . . . . ?
C7 C2 C3 C4 178.73(18) . . . . ?
C5 N1 C1 N2 -179.57(15) . . . . ?
C5 N1 C1 C2 -1.5(2) . . . . ?
C3 C2 C1 N2 180.00(15) . . . . ?
C3 C2 C1 N1 1.9(2) . . . . ?
C20 C15 C14 C13 -5.5(2) . . . . ?
C20 C15 C14 C19 179.29(15) . . . . ?
C4 C5 C2A C1 0.1(3) . . . . ?
C4 C5 C2A C6 -179.05(18) . . . . ?
C4 C3 N1A C1 -0.9(3) . . . . ?
C4 C3 N1A C7 178.73(18) . . . . ?
C21 C19 C14 C13 9.6(3) . . . . ?
C21 C19 C14 C15 -175.20(18) . . . . ?
C21 C19 C18 C17 176.12(18) . . . . ?
N1A C1 C2A C6 177.59(16) . . . . ?
N1A C1 C2A C5 -1.5(2) . . . . ?
N1A C3 C4 C5 -0.5(3) . . . . ?
C2A C1 N1A C7 -177.74(15) . . . . ?
C2A C1 N1A C3 1.9(2) . . . . ?
C2A C5 C4 C3 0.9(3) . . . . ?


#----------------------------------------------------------------------------#
#                   SHELX RES FILE                                           #
#----------------------------------------------------------------------------#

####################################################################### 
# 
# 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_22MA073_ER-0503
_database_code_depnum_ccdc_archive 'CCDC 2297425'
loop_
_audit_author_name
_audit_author_address
'Simon Grabowsky'
;University of Bern
Switzerland
;
_audit_update_record             
;
2023-09-25 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;

_audit_creation_date             2022-09-09T14:50:55-00:00

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C16 H19 Cl2 N3 O Pd, C H2 Cl2'
_chemical_formula_sum            'C17 H21 Cl4 N3 O Pd'
_chemical_formula_weight         531.57
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_Int_Tables_number      29
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   19.4911(2)
_cell_length_b                   9.94886(11)
_cell_length_c                   21.9647(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4259.27(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    173.00(10)
_cell_measurement_reflns_used    33002
_cell_measurement_theta_min      2.079
_cell_measurement_theta_max      31.279

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.086
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_F_000             2128
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0921
0 0 1 0.0561
0 0 -1 0.0297
0 -1 -1 0.0723
-1 1 -1 0.07
1 -1 1 0.0788
1 0 1 0.0823
-1 0 -1 0.0907
0 -1 0 0.074
1 1 1 0.0859
-1 -1 -1 0.0592
-1 -1 0 0.0617
1 1 0 0.0804
1 0 0 0.1006
-1 0 0 0.099
-20 -9 6 0.0669
-12 13 -2 0.066
23 -8 -1 0.0858
15 11 -6 0.0765
-15 -8 19 0.061
-13 3 26 0.0588
-2 -11 19 0.065
-5 10 21 0.0628
3 -8 25 0.0638
8 5 28 0.0628
11 -3 27 0.0653
23 5 13 0.0858
23 -5 13 0.0787


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.385
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
        Numerical absorption correction based on gaussian integration over
        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.781
_shelx_estimated_absorpt_T_max   0.892

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      173.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0965
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0165521
_diffrn_orient_matrix_ub_12      -0.0146119
_diffrn_orient_matrix_ub_13      -0.0279625
_diffrn_orient_matrix_ub_21      -0.0315133
_diffrn_orient_matrix_ub_22      -0.0090549
_diffrn_orient_matrix_ub_23      0.0156596
_diffrn_orient_matrix_ub_31      -0.0076158
_diffrn_orient_matrix_ub_32      0.0691839
_diffrn_orient_matrix_ub_33      -0.0039128
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_number            62815
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.047
_diffrn_reflns_theta_max         30.41
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_coverage         0.937
_reflns_number_total             12785
_reflns_number_gt                11880
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1560P)²+10.5185P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         12785
_refine_ls_number_parameters     474
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0892
_refine_ls_wR_factor_ref         0.2198
_refine_ls_wR_factor_gt          0.2152
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.19(6)
_refine_diff_density_max         11.27
_refine_diff_density_min         -1.355
_refine_diff_density_rms         0.279

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0031 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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 0.65334(3) 0.39357(6) 0.62550(3) 0.02115(17) Uani 1 1 d . . . . .
Pd2 Pd 0.60966(3) 0.89155(6) 0.37172(3) 0.02063(16) Uani 1 1 d . . . . .
Cl1 Cl 0.72221(12) 0.4698(3) 0.70257(11) 0.0301(4) Uani 1 1 d . . . . .
Cl4 Cl 0.70337(14) 1.0039(3) 0.33463(12) 0.0372(6) Uani 1 1 d . . . . .
Cl3 Cl 0.54012(12) 0.9805(2) 0.29786(11) 0.0294(4) Uani 1 1 d . . . . .
Cl2 Cl 0.56108(13) 0.5107(3) 0.66437(11) 0.0331(5) Uani 1 1 d . . . . .
Cl5 Cl 0.9218(2) 0.8928(4) 0.59656(18) 0.0532(8) Uani 1 1 d . . . . .
Cl6 Cl 0.8649(2) 0.6718(4) 0.6682(2) 0.0652(11) Uani 1 1 d . . . . .
Cl8 Cl 0.3348(3) 0.4076(4) 0.3935(2) 0.0617(10) Uani 1 1 d . . . . .
Cl7 Cl 0.3977(2) 0.1768(4) 0.3354(3) 0.0692(13) Uani 1 1 d . . . . .
O1 O 0.7520(4) 0.1418(8) 0.5068(4) 0.0337(15) Uani 1 1 d . . . . .
O2 O 0.5088(4) 0.6458(8) 0.4897(4) 0.0318(15) Uani 1 1 d . . . . .
N6 N 0.4597(4) 0.6945(8) 0.3323(4) 0.0216(13) Uani 1 1 d . . . . .
N1 N 0.6028(4) 0.3254(8) 0.5508(4) 0.0250(15) Uani 1 1 d . . . . .
C6 C 0.7134(5) 0.2160(9) 0.5356(4) 0.0223(15) Uani 1 1 d . . . . .
N2 N 0.7278(4) 0.2793(8) 0.5886(4) 0.0235(14) Uani 1 1 d . . . . .
N5 N 0.5344(4) 0.7781(8) 0.4071(3) 0.0216(13) Uani 1 1 d . . . . .
N3 N 0.8004(4) 0.1851(8) 0.6634(4) 0.0251(15) Uani 1 1 d . . . . .
N4 N 0.6601(4) 0.8165(8) 0.4456(4) 0.0236(14) Uani 1 1 d . . . . .
C30 C 0.5299(6) 0.4862(11) 0.3332(6) 0.037(2) Uani 1 1 d . . . . .
H30A H 0.492036 0.424965 0.321567 0.044 Uiso 1 1 calc R U . . .
H30B H 0.529173 0.496177 0.378015 0.044 Uiso 1 1 calc R U . . .
C21 C 0.6201(5) 0.7405(9) 0.4819(4) 0.0228(16) Uani 1 1 d . . . . .
C23 C 0.4678(4) 0.7683(8) 0.3844(4) 0.0208(15) Uani 1 1 d . . . . .
C22 C 0.5480(5) 0.7172(9) 0.4612(4) 0.0233(16) Uani 1 1 d . . . . .
C4 C 0.6184(6) 0.1931(11) 0.4596(5) 0.032(2) Uani 1 1 d . . . . .
H4 H 0.647063 0.140218 0.434162 0.038 Uiso 1 1 calc R U . . .
C9 C 0.9144(5) 0.3082(11) 0.6163(5) 0.033(2) Uani 1 1 d . . . . .
H9 H 0.954465 0.348113 0.599576 0.04 Uiso 1 1 calc R U . . .
C5 C 0.6414(5) 0.2452(10) 0.5144(4) 0.0260(17) Uani 1 1 d . . . . .
C20 C 0.6437(6) 0.6882(10) 0.5357(5) 0.0299(19) Uani 1 1 d . . . . .
H20 H 0.614229 0.635454 0.560539 0.036 Uiso 1 1 calc R U . . .
C10 C 0.9184(5) 0.2313(11) 0.6687(6) 0.034(2) Uani 1 1 d . . . . .
H10 H 0.961163 0.221563 0.689003 0.041 Uiso 1 1 calc R U . . .
C13 C 0.7397(6) 0.1146(10) 0.6887(5) 0.032(2) Uani 1 1 d . . . . .
H13A H 0.698583 0.171588 0.683042 0.038 Uiso 1 1 calc R U . . .
H13B H 0.746365 0.100916 0.732939 0.038 Uiso 1 1 calc R U . . .
C25 C 0.3471(5) 0.8182(11) 0.3834(5) 0.0308(19) Uani 1 1 d . . . . .
H25 H 0.307802 0.858827 0.401166 0.037 Uiso 1 1 calc R U . . .
C26 C 0.3403(5) 0.7434(11) 0.3301(5) 0.0304(19) Uani 1 1 d . . . . .
H26 H 0.296706 0.734381 0.31118 0.036 Uiso 1 1 calc R U . . .
C29 C 0.5183(5) 0.6211(9) 0.3043(4) 0.0262(17) Uani 1 1 d . . . . .
H29A H 0.560456 0.675802 0.308405 0.031 Uiso 1 1 calc R U . . .
H29B H 0.509198 0.60864 0.260283 0.031 Uiso 1 1 calc R U . . .
C11 C 0.8617(5) 0.1699(11) 0.6911(5) 0.0311(19) Uani 1 1 d . . . . .
H11 H 0.865175 0.115802 0.726594 0.037 Uiso 1 1 calc R U . . .
C3 C 0.5494(6) 0.2231(12) 0.4437(6) 0.037(2) Uani 1 1 d . . . . .
H3 H 0.530351 0.187603 0.407251 0.045 Uiso 1 1 calc R U . . .
C27 C 0.3970(5) 0.6825(11) 0.3051(5) 0.0292(19) Uani 1 1 d . . . . .
H27 H 0.392594 0.631831 0.268615 0.035 Uiso 1 1 calc R U . . .
C2 C 0.5108(6) 0.3025(12) 0.4803(6) 0.038(3) Uani 1 1 d . . . . .
H2 H 0.464844 0.323419 0.469338 0.046 Uiso 1 1 calc R U . . .
C7 C 0.7935(4) 0.2620(9) 0.6130(4) 0.0215(15) Uani 1 1 d . . . . .
C24 C 0.4107(5) 0.8339(10) 0.4105(5) 0.0263(17) Uani 1 1 d . . . . .
C18 C 0.7523(6) 0.7899(11) 0.5154(6) 0.036(2) Uani 1 1 d . . . . .
H18 H 0.798793 0.807239 0.525781 0.043 Uiso 1 1 calc R U . . .
C19 C 0.7111(6) 0.7131(10) 0.5538(5) 0.033(2) Uani 1 1 d . . . . .
H19 H 0.728293 0.678658 0.591137 0.039 Uiso 1 1 calc R U . . .
C17 C 0.7245(5) 0.8410(11) 0.4616(5) 0.033(2) Uani 1 1 d . . . . .
H17 H 0.752485 0.894597 0.43578 0.039 Uiso 1 1 calc R U . . .
C28 C 0.4202(6) 0.9168(11) 0.4666(5) 0.033(2) Uani 1 1 d . . . . .
H28A H 0.412533 0.86083 0.502649 0.05 Uiso 1 1 calc R U . . .
H28B H 0.387386 0.991372 0.466395 0.05 Uiso 1 1 calc R U . . .
H28C H 0.467064 0.952616 0.467456 0.05 Uiso 1 1 calc R U . . .
C1 C 0.5381(5) 0.3528(11) 0.5335(5) 0.0298(19) Uani 1 1 d . . . . .
H1 H 0.510481 0.408389 0.558721 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8511(5) 0.3264(9) 0.5883(5) 0.0260(17) Uani 1 1 d . . . . .
C14 C 0.7280(7) -0.0197(13) 0.6585(6) 0.041(2) Uani 1 1 d . . . . .
H14A H 0.767181 -0.079972 0.667358 0.049 Uiso 1 1 calc R U . . .
H14B H 0.725404 -0.007329 0.613828 0.049 Uiso 1 1 calc R U . . .
C34 C 0.3319(9) 0.2966(15) 0.3308(8) 0.057(4) Uani 1 1 d . . . . .
H34A H 0.28691 0.250368 0.329921 0.068 Uiso 1 1 calc R U . . .
H34B H 0.336709 0.348366 0.292518 0.068 Uiso 1 1 calc R U . . .
C12 C 0.8447(6) 0.4137(12) 0.5325(6) 0.035(2) Uani 1 1 d . . . . .
H12A H 0.823226 0.362171 0.499581 0.052 Uiso 1 1 calc R U . . .
H12B H 0.890385 0.443482 0.519592 0.052 Uiso 1 1 calc R U . . .
H12C H 0.816329 0.492277 0.541986 0.052 Uiso 1 1 calc R U . . .
C32 C 0.6592(8) 0.4904(19) 0.3445(10) 0.069(5) Uani 1 1 d . . . . .
H32A H 0.684786 0.543706 0.314707 0.103 Uiso 1 1 calc R U . . .
H32B H 0.689282 0.421444 0.361885 0.103 Uiso 1 1 calc R U . . .
H32C H 0.642475 0.549263 0.377096 0.103 Uiso 1 1 calc R U . . .
C31 C 0.5989(8) 0.4237(13) 0.3136(7) 0.047(3) Uani 1 1 d . . . . .
H31A H 0.59883 0.326683 0.323678 0.056 Uiso 1 1 calc R U . . .
H31B H 0.604057 0.432383 0.268922 0.056 Uiso 1 1 calc R U . . .
C33 C 0.9343(7) 0.7851(13) 0.6604(6) 0.045(3) Uani 1 1 d . . . . .
H33A H 0.97746 0.734043 0.655175 0.054 Uiso 1 1 calc R U . . .
H33B H 0.938431 0.839976 0.697848 0.054 Uiso 1 1 calc R U . . .
C15 C 0.6625(10) -0.0834(17) 0.6810(9) 0.061(4) Uani 1 1 d . . . . .
H15A H 0.66054 -0.076874 0.72599 0.074 Uiso 1 1 calc R U . . .
H15B H 0.662111 -0.179818 0.669933 0.074 Uiso 1 1 calc R U . . .
C16 C 0.5970(11) -0.012(3) 0.6527(16) 0.115(12) Uani 1 1 d . . . . .
H16A H 0.556359 -0.067651 0.659754 0.172 Uiso 1 1 calc R U . . .
H16B H 0.603736 0.000108 0.608773 0.172 Uiso 1 1 calc R U . . .
H16C H 0.590577 0.07608 0.671924 0.172 Uiso 1 1 calc R U . . .


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.290(2) . ?
Pd1 Cl2 2.307(2) . ?
Pd1 N1 2.029(9) . ?
Pd1 N2 2.014(7) . ?
Pd2 Cl4 2.291(2) . ?
Pd2 Cl3 2.292(2) . ?
Pd2 N5 2.008(7) . ?
Pd2 N4 2.038(8) . ?
Cl5 C33 1.782(14) . ?
Cl6 C33 1.769(15) . ?
Cl8 C34 1.767(17) . ?
Cl7 C34 1.754(16) . ?
O1 C6 1.228(12) . ?
O2 C22 1.217(11) . ?
N6 C23 1.368(11) . ?
N6 C29 1.489(13) . ?
N6 C27 1.367(11) . ?
N1 C5 1.357(13) . ?
N1 C1 1.345(12) . ?
C6 N2 1.354(12) . ?
C6 C5 1.508(13) . ?
N2 C7 1.398(11) . ?
N5 C23 1.393(11) . ?
N5 C22 1.359(11) . ?
N3 C13 1.483(14) . ?
N3 C11 1.349(13) . ?
N3 C7 1.353(11) . ?
N4 C21 1.347(12) . ?
N4 C17 1.328(12) . ?
C30 H30A 0.99 . ?
C30 H30B 0.99 . ?
C30 C29 1.501(15) . ?
C30 C31 1.544(17) . ?
C21 C22 1.495(13) . ?
C21 C20 1.371(13) . ?
C23 C24 1.412(12) . ?
C4 H4 0.95 . ?
C4 C5 1.384(14) . ?
C4 C3 1.421(15) . ?
C9 H9 0.95 . ?
C9 C10 1.384(18) . ?
C9 C8 1.389(14) . ?
C20 H20 0.95 . ?
C20 C19 1.394(15) . ?
C10 H10 0.95 . ?
C10 C11 1.356(16) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C13 C14 1.509(16) . ?
C25 H25 0.95 . ?
C25 C26 1.393(15) . ?
C25 C24 1.384(13) . ?
C26 H26 0.95 . ?
C26 C27 1.375(15) . ?
C29 H29A 0.99 . ?
C29 H29B 0.99 . ?
C11 H11 0.95 . ?
C3 H3 0.95 . ?
C3 C2 1.356(19) . ?
C27 H27 0.95 . ?
C2 H2 0.95 . ?
C2 C1 1.379(16) . ?
C7 C8 1.402(13) . ?
C24 C28 1.493(14) . ?
C18 H18 0.95 . ?
C18 C19 1.393(17) . ?
C18 C17 1.397(15) . ?
C19 H19 0.95 . ?
C17 H17 0.95 . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C28 H28C 0.98 . ?
C1 H1 0.95 . ?
C8 C12 1.507(15) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C14 C15 1.51(2) . ?
C34 H34A 0.99 . ?
C34 H34B 0.99 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C32 H32A 0.98 . ?
C32 H32B 0.98 . ?
C32 H32C 0.98 . ?
C32 C31 1.51(3) . ?
C31 H31A 0.99 . ?
C31 H31B 0.99 . ?
C33 H33A 0.99 . ?
C33 H33B 0.99 . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C15 C16 1.59(3) . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?

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 90.92(10) . . ?
N1 Pd1 Cl1 173.0(3) . . ?
N1 Pd1 Cl2 95.2(3) . . ?
N2 Pd1 Cl1 93.5(2) . . ?
N2 Pd1 Cl2 174.9(2) . . ?
N2 Pd1 N1 80.6(3) . . ?
Cl4 Pd2 Cl3 91.80(9) . . ?
N5 Pd2 Cl4 174.0(2) . . ?
N5 Pd2 Cl3 93.4(2) . . ?
N5 Pd2 N4 80.7(3) . . ?
N4 Pd2 Cl4 94.4(2) . . ?
N4 Pd2 Cl3 171.9(2) . . ?
C23 N6 C29 121.5(7) . . ?
C27 N6 C23 121.1(8) . . ?
C27 N6 C29 117.5(8) . . ?
C5 N1 Pd1 113.9(6) . . ?
C1 N1 Pd1 128.0(8) . . ?
C1 N1 C5 118.1(9) . . ?
O1 C6 N2 126.5(9) . . ?
O1 C6 C5 121.8(9) . . ?
N2 C6 C5 111.7(8) . . ?
C6 N2 Pd1 117.3(6) . . ?
C6 N2 C7 117.5(7) . . ?
C7 N2 Pd1 125.2(6) . . ?
C23 N5 Pd2 125.5(6) . . ?
C22 N5 Pd2 116.5(6) . . ?
C22 N5 C23 117.6(7) . . ?
C11 N3 C13 119.0(9) . . ?
C11 N3 C7 121.4(8) . . ?
C7 N3 C13 119.6(8) . . ?
C21 N4 Pd2 113.5(6) . . ?
C17 N4 Pd2 126.9(7) . . ?
C17 N4 C21 119.6(9) . . ?
H30A C30 H30B 107.9 . . ?
C29 C30 H30A 109.2 . . ?
C29 C30 H30B 109.2 . . ?
C29 C30 C31 111.9(10) . . ?
C31 C30 H30A 109.2 . . ?
C31 C30 H30B 109.2 . . ?
N4 C21 C22 116.8(8) . . ?
N4 C21 C20 122.0(9) . . ?
C20 C21 C22 121.2(9) . . ?
N6 C23 N5 116.3(8) . . ?
N6 C23 C24 119.8(8) . . ?
N5 C23 C24 123.8(8) . . ?
O2 C22 N5 125.9(9) . . ?
O2 C22 C21 121.6(9) . . ?
N5 C22 C21 112.3(8) . . ?
C5 C4 H4 121.9 . . ?
C5 C4 C3 116.2(11) . . ?
C3 C4 H4 121.9 . . ?
C10 C9 H9 120.3 . . ?
C10 C9 C8 119.4(10) . . ?
C8 C9 H9 120.3 . . ?
N1 C5 C6 116.5(8) . . ?
N1 C5 C4 123.6(9) . . ?
C4 C5 C6 119.9(9) . . ?
C21 C20 H20 120.2 . . ?
C21 C20 C19 119.6(10) . . ?
C19 C20 H20 120.2 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(9) . . ?
C11 C10 H10 119.9 . . ?
N3 C13 H13A 109.2 . . ?
N3 C13 H13B 109.2 . . ?
N3 C13 C14 112.0(9) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.5(10) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 C25 119.6(9) . . ?
C27 C26 H26 120.2 . . ?
N6 C29 C30 112.2(8) . . ?
N6 C29 H29A 109.2 . . ?
N6 C29 H29B 109.2 . . ?
C30 C29 H29A 109.2 . . ?
C30 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
N3 C11 C10 120.5(10) . . ?
N3 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C4 C3 H3 120 . . ?
C2 C3 C4 120.1(11) . . ?
C2 C3 H3 120 . . ?
N6 C27 C26 120.4(9) . . ?
N6 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C3 C2 H2 120 . . ?
C3 C2 C1 120.0(10) . . ?
C1 C2 H2 120 . . ?
N2 C7 C8 122.0(8) . . ?
N3 C7 N2 118.3(8) . . ?
N3 C7 C8 119.7(8) . . ?
C23 C24 C28 119.4(9) . . ?
C25 C24 C23 118.6(9) . . ?
C25 C24 C28 122.0(9) . . ?
C19 C18 H18 120.4 . . ?
C19 C18 C17 119.2(9) . . ?
C17 C18 H18 120.4 . . ?
C20 C19 H19 121 . . ?
C18 C19 C20 117.9(10) . . ?
C18 C19 H19 121 . . ?
N4 C17 C18 121.6(10) . . ?
N4 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N1 C1 C2 121.9(10) . . ?
N1 C1 H1 119 . . ?
C2 C1 H1 119 . . ?
C9 C8 C7 118.7(10) . . ?
C9 C8 C12 120.6(9) . . ?
C7 C8 C12 120.7(9) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 C15 110.8(11) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
Cl8 C34 H34A 109.5 . . ?
Cl8 C34 H34B 109.5 . . ?
Cl7 C34 Cl8 110.9(8) . . ?
Cl7 C34 H34A 109.5 . . ?
Cl7 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
C30 C31 H31A 109.2 . . ?
C30 C31 H31B 109.2 . . ?
C32 C31 C30 112.0(11) . . ?
C32 C31 H31A 109.2 . . ?
C32 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
Cl5 C33 H33A 109.5 . . ?
Cl5 C33 H33B 109.5 . . ?
Cl6 C33 Cl5 110.8(7) . . ?
Cl6 C33 H33A 109.5 . . ?
Cl6 C33 H33B 109.5 . . ?
H33A C33 H33B 108.1 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C14 C15 C16 111.3(15) . . ?
H15A C15 H15B 108 . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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 N1 C5 C6 1.9(10) . . . . ?
Pd1 N1 C5 C4 -176.7(8) . . . . ?
Pd1 N1 C1 C2 178.0(8) . . . . ?
Pd1 N2 C7 N3 73.0(10) . . . . ?
Pd1 N2 C7 C8 -104.2(9) . . . . ?
Pd2 N5 C23 N6 74.4(9) . . . . ?
Pd2 N5 C23 C24 -102.8(9) . . . . ?
Pd2 N5 C22 O2 179.4(8) . . . . ?
Pd2 N5 C22 C21 -3.9(10) . . . . ?
Pd2 N4 C21 C22 3.2(10) . . . . ?
Pd2 N4 C21 C20 -175.8(8) . . . . ?
Pd2 N4 C17 C18 176.1(8) . . . . ?
O1 C6 N2 Pd1 -179.4(8) . . . . ?
O1 C6 N2 C7 1.7(14) . . . . ?
O1 C6 C5 N1 178.1(9) . . . . ?
O1 C6 C5 C4 -3.3(14) . . . . ?
N6 C23 C24 C25 1.9(13) . . . . ?
N6 C23 C24 C28 -178.6(8) . . . . ?
C6 N2 C7 N3 -108.2(9) . . . . ?
C6 N2 C7 C8 74.7(11) . . . . ?
N2 C6 C5 N1 -1.1(12) . . . . ?
N2 C6 C5 C4 177.6(9) . . . . ?
N2 C7 C8 C9 177.7(9) . . . . ?
N2 C7 C8 C12 -2.3(14) . . . . ?
N5 C23 C24 C25 179.0(9) . . . . ?
N5 C23 C24 C28 -1.5(13) . . . . ?
N3 C13 C14 C15 -174.9(11) . . . . ?
N3 C7 C8 C9 0.6(13) . . . . ?
N3 C7 C8 C12 -179.4(9) . . . . ?
N4 C21 C22 O2 177.2(9) . . . . ?
N4 C21 C22 N5 0.4(12) . . . . ?
N4 C21 C20 C19 -0.5(15) . . . . ?
C21 N4 C17 C18 -0.1(16) . . . . ?
C21 C20 C19 C18 -0.7(16) . . . . ?
C23 N6 C29 C30 83.5(11) . . . . ?
C23 N6 C27 C26 -0.8(14) . . . . ?
C23 N5 C22 O2 6.0(15) . . . . ?
C23 N5 C22 C21 -177.3(8) . . . . ?
C22 N5 C23 N6 -112.9(9) . . . . ?
C22 N5 C23 C24 69.9(11) . . . . ?
C22 C21 C20 C19 -179.4(9) . . . . ?
C4 C3 C2 C1 -0.8(17) . . . . ?
C9 C10 C11 N3 -1.3(16) . . . . ?
C5 N1 C1 C2 -0.3(15) . . . . ?
C5 C6 N2 Pd1 -0.3(10) . . . . ?
C5 C6 N2 C7 -179.2(8) . . . . ?
C5 C4 C3 C2 2.1(16) . . . . ?
C20 C21 C22 O2 -3.8(15) . . . . ?
C20 C21 C22 N5 179.4(9) . . . . ?
C10 C9 C8 C7 -2.3(14) . . . . ?
C10 C9 C8 C12 177.7(10) . . . . ?
C13 N3 C11 C10 179.1(9) . . . . ?
C13 N3 C7 N2 4.1(13) . . . . ?
C13 N3 C7 C8 -178.7(8) . . . . ?
C13 C14 C15 C16 75(2) . . . . ?
C25 C26 C27 N6 0.4(16) . . . . ?
C26 C25 C24 C23 -2.4(15) . . . . ?
C26 C25 C24 C28 178.1(10) . . . . ?
C29 N6 C23 N5 4.2(12) . . . . ?
C29 N6 C23 C24 -178.5(8) . . . . ?
C29 N6 C27 C26 177.4(9) . . . . ?
C29 C30 C31 C32 74.8(15) . . . . ?
C11 N3 C13 C14 -93.7(12) . . . . ?
C11 N3 C7 N2 -176.5(8) . . . . ?
C11 N3 C7 C8 0.7(14) . . . . ?
C3 C4 C5 N1 -2.7(16) . . . . ?
C3 C4 C5 C6 178.8(9) . . . . ?
C3 C2 C1 N1 -0.1(17) . . . . ?
C27 N6 C23 N5 -177.6(8) . . . . ?
C27 N6 C23 C24 -0.3(13) . . . . ?
C27 N6 C29 C30 -94.7(11) . . . . ?
C7 N3 C13 C14 85.8(11) . . . . ?
C7 N3 C11 C10 -0.4(15) . . . . ?
C24 C25 C26 C27 1.3(16) . . . . ?
C19 C18 C17 N4 -1.0(17) . . . . ?
C17 N4 C21 C22 179.8(9) . . . . ?
C17 N4 C21 C20 0.9(15) . . . . ?
C17 C18 C19 C20 1.4(17) . . . . ?
C1 N1 C5 C6 -179.6(8) . . . . ?
C1 N1 C5 C4 1.8(15) . . . . ?
C8 C9 C10 C11 2.7(16) . . . . ?
C31 C30 C29 N6 -168.1(9) . . . . ?

#----------------------------------------------------------------------------#
#                   VALIDATION REPLY FORM                                    #
#----------------------------------------------------------------------------#

_vrf_PLAT094_22MA073_ER-0503     
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       8.32 Report
RESPONSE: The high residuals correspond to a pseudo translation of 0.25 
along the b direction for the position of the heavy element. Unfortunately 
the pseudo translation could not be solved.
;
_vrf_PLAT097_22MA073_ER-0503     
;
PROBLEM: Large Reported Max.  (Positive) Residual Density      11.27 eA-3  
RESPONSE: The high residuals correspond to a pseudo translation of 0.25 
along the b direction for the position of the heavy element. Unfortunately 
the pseudo translation could not be solved.
;
_vrf_PLAT971_22MA073_ER-0503     
;
PROBLEM: Check Calcd Resid. Dens.  1.79Ang From Cl2            10.54 eA-3  
RESPONSE: The high residuals correspond to a pseudo translation of 0.25 
along the b direction for the position of the heavy element. Unfortunately 
the pseudo translation could not be solved.
;
_vrf_PLAT973_22MA073_ER-0503     
;
PROBLEM: Check Calcd Positive Resid. Density on       Pd1       3.04 eA-3  
RESPONSE: The high residuals correspond to a pseudo translation of 0.25 
along the b direction for the position of the heavy element. Unfortunately 
the pseudo translation could not be solved.
;

#----------------------------------------------------------------------------#
#                   SHELX RES FILE                                           #
#----------------------------------------------------------------------------#

####################################################################### 
# 
# 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_22MA115_ER-0267
_database_code_depnum_ccdc_archive 'CCDC 2297424'
loop_
_audit_author_name
_audit_author_address
'Simon Grabowsky'
;University of Bern
Switzerland
;
_audit_update_record             
;
2023-09-25 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_audit_creation_date             2023-02-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_formula_moiety         'C12 H11 Cl2 N3 O Pd'
_chemical_formula_sum            'C12 H11 Cl2 N3 O Pd'
_chemical_formula_weight         390.561
_chemical_oxdiff_formula         'C48  H44  Cl8  N12  O4  Pd4  '
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01810 0.00910 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
Cl 0.36390 0.70180 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
O 0.04920 0.03220 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
N 0.03110 0.01800 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
Pd 0.12150 3.93370 19.33190 15.50170 5.29537 0.60584 0.69866 7.98929 25.20520
76.89860 5.26593017578
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   10.44149(12)
_cell_length_b                   11.38265(13)
_cell_length_c                   11.56249(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.8439(10)
_cell_angle_gamma                90
_cell_volume                     1374.07(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25623
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      79.9730
_cell_measurement_theta_min      3.7950
_exptl_absorpt_coefficient_mu    14.435
_exptl_absorpt_correction_T_max  0.504
_exptl_absorpt_correction_T_min  0.110
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.888
_exptl_crystal_description       block
_exptl_crystal_F_000             768
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 2 0.0943
-1 0 -2 0.0861
2 -1 0 0.0669
-1 1 1 0.0775
1 -1 -1 0.0659
-1 1 2 0.0873
1 -1 -2 0.0799
2 -1 -1 0.0545
-2 1 1 0.0586
-2 1 2 0.0735
0 0 1 0.0853
-1 0 2 0.0753
-1 0 1 0.0689
1 0 -1 0.0504
1 0 -2 0.0677
-2 0 1 0.0718
2 0 -1 0.0636
-1 0 0 0.0707
1 0 0 0.0799
-2 -1 2 0.0871
-1 -1 2 0.1007
0 -1 2 0.1035
2 0 1 0.0969
1 1 -2 0.0725
-2 0 -1 0.0817
-2 -1 1 0.0864
1 -1 2 0.0875
1 1 -1 0.0683
-1 -1 1 0.0997
-2 -1 0 0.0879
-2 -2 1 0.0967
2 2 -1 0.0815
1 2 -2 0.0725
1 2 -1 0.0684
-1 -2 1 0.1054
-1 -1 0 0.0933
0 2 -1 0.0652
-1 -2 0 0.1025
1 -1 1 0.0776
-1 2 -1 0.0614
0 1 0 0.0902
1 2 1 0.0974
0 -1 0 0.0974
1 -2 0 0.0795
2 -2 1 0.0707

_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.113
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0006 0.0002 2.0015 0.1185 -0.0208 0.2822
-1.0006 -0.0002 -2.0015 -0.1185 0.0208 -0.2822
1.9970 -1.0004 -0.0003 -0.2033 0.0504 0.2474
-0.9974 1.0005 1.0008 0.2194 -0.0807 -0.0501
0.9974 -1.0005 -1.0008 -0.2194 0.0807 0.0501
-0.9964 1.0006 2.0018 0.3219 -0.0712 0.0347
0.9964 -1.0006 -2.0018 -0.3219 0.0712 -0.0347
1.9960 -1.0005 -1.0013 -0.3059 0.0409 0.1625
-1.9960 1.0005 1.0013 0.3059 -0.0409 -0.1625
-1.9950 1.0006 2.0024 0.4084 -0.0314 -0.0777
0.0010 0.0001 1.0011 0.1025 0.0095 0.0849
-0.9967 0.0003 2.0027 0.2915 0.0588 0.0574
-0.9977 0.0001 1.0016 0.1890 0.0493 -0.0275
0.9977 -0.0001 -1.0016 -0.1890 -0.0493 0.0275
0.9967 -0.0003 -2.0027 -0.2915 -0.0588 -0.0574
-1.9963 0.0002 1.0022 0.2755 0.0891 -0.1399
1.9963 -0.0002 -1.0022 -0.2755 -0.0891 0.1399
-0.9986 0.0000 0.0006 0.0865 0.0398 -0.1124
0.9986 -0.0000 -0.0006 -0.0865 -0.0398 0.1124
-1.9956 -1.0000 2.0041 0.3477 0.2285 -0.0324
-0.9969 -1.0001 2.0036 0.2612 0.1887 0.0800
0.0017 -1.0001 2.0030 0.1747 0.1490 0.1924
1.9983 0.0001 0.9999 -0.0705 -0.0701 0.3097
0.9969 1.0001 -2.0036 -0.2612 -0.1887 -0.0800
-1.9983 -0.0001 -0.9999 0.0705 0.0701 -0.3097
-1.9966 -1.0002 1.0031 0.2452 0.2191 -0.1173
1.0003 -1.0001 2.0024 0.0882 0.1092 0.3048
0.9979 1.0002 -1.0025 -0.1587 -0.1793 0.0049
-0.9979 -1.0002 1.0025 0.1587 0.1793 -0.0049
-1.9975 -1.0003 0.0020 0.1427 0.2096 -0.2022
-1.9968 -2.0005 1.0040 0.2149 0.3490 -0.0947
1.9968 2.0005 -1.0040 -0.2149 -0.3490 0.0947
0.9972 2.0004 -2.0044 -0.2309 -0.3187 -0.1026
0.9982 2.0005 -1.0034 -0.1284 -0.3092 -0.0178
-0.9982 -2.0005 1.0034 0.1284 0.3092 0.0178
-0.9989 -1.0003 0.0015 0.0562 0.1698 -0.0898
-0.0005 2.0005 -1.0028 -0.0419 -0.2695 -0.1302
-0.9992 -2.0006 0.0023 0.0258 0.2998 -0.0671
0.9994 -1.0002 1.0014 -0.0143 0.0997 0.2199
-0.9991 2.0005 -1.0022 0.0446 -0.2297 -0.2426
0.0003 1.0003 -0.0009 0.0303 -0.1300 -0.0226
1.0001 2.0007 0.9987 0.0767 -0.2903 0.1520
-0.0003 -1.0003 0.0009 -0.0303 0.1300 0.0226
0.9981 -2.0007 0.0012 -0.1472 0.2202 0.1577
1.9977 -2.0006 1.0016 -0.1311 0.1899 0.3550

_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27616
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9997
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         76.44
_diffrn_reflns_theta_min         5.45
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -97.00 -35.00   0.50    0.15    --  -23.00 170.00 111.00  124
  2  ω    -62.00  -5.00   0.50    0.15    --  -23.00 115.00 -31.00  114
  3  ω     27.00  88.00   0.50    0.15    --   47.92-115.00-121.00  122
  4  ω     45.00 109.00   0.50    0.60    --  113.25-115.00-121.00  128
  5  ω    -96.00 -10.00   0.50    0.15    --  -23.00 -38.00-150.00  172
  6  ω    -94.00 -44.00   0.50    0.15    --  -23.00-170.00  95.00  100
  7  ω    -36.00  50.00   0.50    0.15    --  -23.00  38.00   0.00  172
  8  ω    -28.00  52.00   0.50    0.15    --  -23.00  15.00-180.00  160
  9  ω    -46.00  50.00   0.50    0.15    --  -23.00  77.00  30.00  192
 10  ω    -26.00  23.00   0.50    0.15    --   47.92 -19.00-120.00   98
 11  ω    -26.00  23.00   0.50    0.15    --   47.92 -19.00 -90.00   98
 12  ω     -1.00  80.00   0.50    0.15    --   47.92 -99.00-180.00  162
 13  ω    101.00 177.00   0.50    0.60    --  113.25  45.00  30.00  152
 14  ω     42.00 102.00   0.50    0.60    --  113.25 -77.00  90.00  120
 15  ω     42.00  68.00   0.50    0.60    --  113.25 -61.00  90.00   52
 16  ω     42.00 106.00   0.50    0.60    --  113.25 -94.00  90.00  128
 17  ω     42.00 106.00   0.50    0.60    --  113.25 -94.00 -30.00  128
 18  ω     97.00 177.00   0.50    0.60    --  113.25  61.00 120.00  160
 19  ω     42.00 102.00   0.50    0.60    --  113.25 -77.00 150.00  120
 20  ω     42.00 106.00   0.50    0.60    --  113.25 -94.00 -90.00  128
 21  ω     42.00  68.00   0.50    0.60    --  113.25 -61.00 -90.00   52
 22  ω     42.00  68.00   0.50    0.60    --  113.25 -61.00-120.00   52
 23  ω    100.00 177.00   0.50    0.60    --  113.25  15.00 -60.00  154
 24  ω    101.00 177.00   0.50    0.60    --  113.25  45.00   0.00  152
 25  ω     42.00 106.00   0.50    0.60    --  113.25 -94.00 150.00  128
 26  ω     91.00 177.00   0.50    0.60    --  113.25  77.00  90.00  172
 27  ω     42.00 102.00   0.50    0.60    --  113.25 -77.00 -30.00  120
 28  ω     42.00 102.00   0.50    0.60    --  113.25 -77.00-120.00  120
 29  ω     42.00 106.00   0.50    0.60    --  113.25 -94.00  30.00  128
 30  ω    101.00 177.00   0.50    0.60    --  113.25  45.00-150.00  152
 31  ω     42.00 106.00   0.50    0.60    --  113.25 -94.00  60.00  128
 32  ω     91.00 177.00   0.50    0.60    --  113.25  77.00  60.00  172
 33  ω     42.00 106.00   0.50    0.60    --  113.25 -94.00-150.00  128
 34  ω     42.00 106.00   0.50    0.60    --  113.25 -94.00 -60.00  128
 35  ω    101.00 177.00   0.50    0.60    --  113.25  45.00-180.00  152
 36  ω    101.00 177.00   0.50    0.60    --  113.25  45.00 150.00  152
 37  ω     42.00 102.00   0.50    0.60    --  113.25 -77.00 120.00  120
 38  ω     42.00 106.00   0.50    0.60    --  113.25 -94.00   0.00  128
 39  ω    100.00 177.00   0.50    0.60    --  113.25  15.00   0.00  154
 40  ω     42.00  68.00   0.50    0.60    --  113.25 -61.00-150.00   52
 41  ω    101.00 177.00   0.50    0.60    --  113.25  45.00  90.00  152
 42  ω     97.00 177.00   0.50    0.60    --  113.25  61.00 150.00  160
 43  ω     91.00 177.00   0.50    0.60    --  113.25  77.00-150.00  172
 44  ω     25.00 121.00   0.50    0.15    --   47.92  77.00 -60.00  192
 45  ω     25.00 121.00   0.50    0.15    --   47.92  77.00 120.00  192
 46  ω     25.00 121.00   0.50    0.15    --   47.92  77.00-150.00  192
 47  ω     25.00 121.00   0.50    0.15    --   47.92  77.00  30.00  192
;
_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      -0.0865575000
_diffrn_orient_matrix_UB_12      0.0304313000
_diffrn_orient_matrix_UB_13      0.1024964000
_diffrn_orient_matrix_UB_21      -0.0398465000
_diffrn_orient_matrix_UB_22      -0.1299221000
_diffrn_orient_matrix_UB_23      0.0095295000
_diffrn_orient_matrix_UB_31      0.1126043000
_diffrn_orient_matrix_UB_32      -0.0225799000
_diffrn_orient_matrix_UB_33      0.0846941000
_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         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -13
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              -9
_reflns_number_gt                2887
_reflns_number_total             2890
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.6249
_refine_diff_density_min         -0.8033
_refine_diff_density_rms         0.1188
_refine_ls_d_res_high            0.7930
_refine_ls_d_res_low             8.1111
_refine_ls_extinction_coef       0.00131(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0453
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    4
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.0453
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+2.5765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0747
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Pd1 Pd 0.37880(5) 0.40190(5) 0.43214(5) 0.0216(4) Uani 1.000000 .
Cl1 Cl 0.33594(6) 0.51104(6) 0.26969(6) 0.02756(19) Uani 1.000000 .
Cl2 Cl 0.20059(7) 0.47568(7) 0.52425(6) 0.0309(2) Uani 1.000000 .
O1 O 0.6965(2) 0.1973(2) 0.3963(2) 0.0374(6) Uani 1.000000 .
N3 N 0.4380(2) 0.2984(2) 0.5649(2) 0.0227(5) Uani 1.000000 .
N2 N 0.5329(2) 0.3266(2) 0.3601(2) 0.0239(5) Uani 1.000000 .
N1 N 0.5108(3) 0.2669(2) 0.1667(2) 0.0312(6) Uani 1.000000 .
C8 C 0.5494(3) 0.2411(3) 0.5459(2) 0.0239(6) Uani 1.000000 .
C1 C 0.5653(3) 0.3408(3) 0.2448(2) 0.0244(6) Uani 1.000000 .
C7 C 0.6028(3) 0.2532(3) 0.4270(3) 0.0260(6) Uani 1.000000 .
C12 C 0.3806(3) 0.2832(3) 0.6673(2) 0.0262(6) Uani 1.000000 .
C2 C 0.6452(3) 0.4287(3) 0.2063(3) 0.0317(6) Uani 1.000000 .
H2 H 0.6864(3) 0.4796(3) 0.2603(3) 0.0380(8) Uiso 1.000000 R
C10 C 0.5480(3) 0.1569(3) 0.7353(3) 0.0317(7) Uani 1.000000 .
C11 C 0.4323(3) 0.2125(3) 0.7529(3) 0.0300(6) Uani 1.000000 .
C9 C 0.6067(3) 0.1710(3) 0.6283(3) 0.0293(6) Uani 1.000000 .
C3 C 0.6653(4) 0.4426(3) 0.0891(3) 0.0403(8) Uani 1.000000 .
C5 C 0.5305(4) 0.2794(3) 0.0528(3) 0.0407(8) Uani 1.000000 .
H5 H 0.4908(4) 0.2264(3) -0.0000(3) 0.0488(10) Uiso 1.000000 R
C4 C 0.6068(4) 0.3672(4) 0.0115(3) 0.0419(8) Uani 1.000000 .
C6 C 0.4262(5) 0.1719(4) 0.2064(4) 0.0480(10) Uani 1.000000 .
H10 H 0.584(4) 0.114(3) 0.787(4) 0.032(10) Uiso 1.000000 .
H3 H 0.715(4) 0.510(4) 0.057(4) 0.047(12) Uiso 1.000000 .
H12 H 0.303(3) 0.320(3) 0.682(3) 0.022(8) Uiso 1.000000 .
H11 H 0.385(5) 0.211(4) 0.821(4) 0.057(13) Uiso 1.000000 .
H9 H 0.690(4) 0.136(3) 0.613(3) 0.028(9) Uiso 1.000000 .
H6a H 0.406(4) 0.126(4) 0.144(4) 0.038(10) Uiso 1.000000 .
H6b H 0.359(6) 0.203(5) 0.244(6) 0.078(18) Uiso 1.000000 .
H4 H 0.604(5) 0.373(5) -0.073(5) 0.061(14) Uiso 1.000000 .
H6c H 0.482(4) 0.119(4) 0.257(4) 0.038(11) Uiso 1.000000 .

loop_
_atom_site_anharm_GC_C_label
_atom_site_anharm_GC_C_111
_atom_site_anharm_GC_C_112
_atom_site_anharm_GC_C_113
_atom_site_anharm_GC_C_122
_atom_site_anharm_GC_C_123
_atom_site_anharm_GC_C_133
_atom_site_anharm_GC_C_222
_atom_site_anharm_GC_C_223
_atom_site_anharm_GC_C_233
_atom_site_anharm_GC_C_333
Pd1 -0.00000012(8) -0.00000011(4) -0.00000016(4) -0.00000008(3) -0.00000008(2)
-0.00000012(3) -0.00000008(6) -0.00000010(3) -0.00000005(3) -0.00000002(6)

loop_
_atom_site_anharm_GC_D_label
_atom_site_anharm_GC_D_1111
_atom_site_anharm_GC_D_1112
_atom_site_anharm_GC_D_1113
_atom_site_anharm_GC_D_1122
_atom_site_anharm_GC_D_1123
_atom_site_anharm_GC_D_1133
_atom_site_anharm_GC_D_1222
_atom_site_anharm_GC_D_1223
_atom_site_anharm_GC_D_1233
_atom_site_anharm_GC_D_1333
_atom_site_anharm_GC_D_2222
_atom_site_anharm_GC_D_2223
_atom_site_anharm_GC_D_2233
_atom_site_anharm_GC_D_2333
_atom_site_anharm_GC_D_3333
Pd1 0.000000069(11) 0.000000012(3) 0.000000072(4) 0.000000006(3)
0.0000000009(14) 0.000000034(3) 0.000000006(2) 0.0000000135(14)
0.0000000053(12) 0.000000049(3) -0.000000022(6) 0.000000005(2) -0.000000003(2)
0.000000010(2) 0.000000024(7)


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 2.2907(8) . ?
Pd1 Cl2 2.3153(9) . ?
Pd1 N3 2.025(2) . ?
Pd1 N2 2.014(2) . ?
O1 C7 1.225(4) . ?
N3 C8 1.355(4) . ?
N3 C12 1.346(4) . ?
N2 C1 1.390(4) . ?
N2 C7 1.346(4) . ?
N1 C1 1.353(4) . ?
N1 C5 1.344(4) . ?
N1 C6 1.474(4) . ?
C8 C7 1.498(4) . ?
C8 C9 1.373(4) . ?
C1 C2 1.380(4) . ?
C12 C11 1.380(4) . ?
C2 C3 1.383(5) . ?
C10 C11 1.381(5) . ?
C10 C9 1.398(4) . ?
C3 C4 1.378(6) . ?
C5 C4 1.368(6) . ?

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 91.82(3) . . ?
N3 Pd1 Cl1 172.38(7) . . ?
N3 Pd1 Cl2 95.79(7) . . ?
N2 Pd1 Cl1 92.25(7) . . ?
N2 Pd1 Cl2 175.51(8) . . ?
N2 Pd1 N3 80.16(10) . . ?
C8 N3 Pd1 114.25(18) . . ?
C12 N3 Pd1 127.3(2) . . ?
C12 N3 C8 118.4(2) . . ?
C1 N2 Pd1 123.69(19) . . ?
C7 N2 Pd1 117.13(19) . . ?
C7 N2 C1 119.1(2) . . ?
C5 N1 C1 121.3(3) . . ?
C6 N1 C1 119.8(3) . . ?
C6 N1 C5 119.0(3) . . ?
C7 C8 N3 115.9(2) . . ?
C9 C8 N3 122.3(3) . . ?
C9 C8 C7 121.8(3) . . ?
N1 C1 N2 117.5(3) . . ?
C2 C1 N2 123.4(3) . . ?
C2 C1 N1 119.0(3) . . ?
N2 C7 O1 125.8(3) . . ?
C8 C7 O1 121.9(3) . . ?
C8 C7 N2 112.3(2) . . ?
C11 C12 N3 122.1(3) . . ?
C3 C2 C1 120.0(3) . . ?
C9 C10 C11 118.3(3) . . ?
C10 C11 C12 119.7(3) . . ?
C10 C9 C8 119.2(3) . . ?
C4 C3 C2 119.6(3) . . ?
C4 C5 N1 121.2(3) . . ?
C5 C4 C3 118.8(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 N3 C8 C7 -6.2(2) . . . . ?
Pd1 N3 C8 C9 177.2(2) . . . . ?
Pd1 N3 C12 C11 -178.1(3) . . . . ?
Pd1 N2 C1 N1 -86.4(2) . . . . ?
Pd1 N2 C1 C2 90.8(3) . . . . ?
Pd1 N2 C7 O1 177.5(2) . . . . ?
Pd1 N2 C7 C8 0.4(2) . . . . ?
O1 C7 N2 C1 1.4(4) . . . . ?
O1 C7 C8 N3 -173.4(3) . . . . ?
O1 C7 C8 C9 3.2(4) . . . . ?
N3 C8 C7 N2 3.9(3) . . . . ?
N3 C8 C9 C10 0.6(4) . . . . ?
N3 C12 C11 C10 1.4(4) . . . . ?
N2 C1 N1 C5 175.7(3) . . . . ?
N2 C1 N1 C6 -3.3(4) . . . . ?
N2 C1 C2 C3 -175.1(3) . . . . ?
N2 C7 C8 C9 -179.6(3) . . . . ?
N1 C1 C2 C3 2.1(3) . . . . ?
N1 C5 C4 C3 0.9(5) . . . . ?
C8 C9 C10 C11 1.5(4) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C12 C11 C10 C9 -2.5(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?


_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 2.398
_oxdiff_exptl_absorpt_empirical_full_min 0.646
