# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

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

data_compound_1
_database_code_depnum_ccdc_archive 'CCDC 2354124'
loop_
_audit_author_name
_audit_author_address
'Michael Seidl'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_audit_creation_date             2024-05-08
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H24 N4'
_chemical_formula_sum            'C16 H24 N4'
_chemical_formula_weight         272.39
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.74140(10)
_cell_length_b                   11.2691(2)
_cell_length_c                   13.8933(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1525.16(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9480
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.584
_cell_measurement_theta_min      3.129
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
? was used for absorption correction.
wR2(int) was 0.1456 before and 0.0343 after correction.
The Ratio of minimum to maximum transmission is 0.9499.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15931
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.591
_diffrn_reflns_theta_min         3.445
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4145
_reflns_number_total             4280
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_collection       'Bruker Apex III'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 1750 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         4280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0689P)²+0.3251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1132
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C11(H11), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.12704(16) 0.75937(12) 0.42689(11) 0.0230(3) Uani 1 1 d . . . . .
N2 N 0.33259(15) 0.43351(12) 0.39168(11) 0.0189(3) Uani 1 1 d . . . . .
N3 N 0.24360(14) 0.26139(12) 0.47596(9) 0.0155(3) Uani 1 1 d . . . . .
N4 N 0.26163(15) 0.25124(12) 0.31940(9) 0.0176(3) Uani 1 1 d . . . . .
C1 C 0.26425(18) 0.74796(14) 0.42423(12) 0.0200(3) Uani 1 1 d . . . . .
H1 H 0.317256 0.818533 0.428484 0.024 Uiso 1 1 calc R U . . .
C2 C 0.33438(17) 0.64240(13) 0.41585(12) 0.0180(3) Uani 1 1 d . . . . .
H2 H 0.431896 0.642172 0.415519 0.022 Uiso 1 1 calc R U . . .
C3 C 0.26145(16) 0.53415(13) 0.40771(10) 0.0149(3) Uani 1 1 d . . . . .
C4 C 0.11617(17) 0.54542(13) 0.41239(11) 0.0164(3) Uani 1 1 d . . . . .
H4 H 0.059626 0.476811 0.409639 0.020 Uiso 1 1 calc R U . . .
C5 C 0.05761(17) 0.65672(14) 0.42096(12) 0.0196(3) Uani 1 1 d . . . . .
H5 H -0.039761 0.660878 0.422803 0.024 Uiso 1 1 calc R U . . .
C6 C 0.27607(16) 0.32547(14) 0.39559(11) 0.0161(3) Uani 1 1 d . . . . .
C7 C 0.20994(16) 0.14429(13) 0.44936(11) 0.0154(3) Uani 1 1 d . . . . .
C8 C 0.22107(17) 0.13928(13) 0.35205(11) 0.0169(3) Uani 1 1 d . . . . .
C9 C 0.1697(2) 0.04822(15) 0.51747(12) 0.0221(3) Uani 1 1 d . . . . .
H9A H 0.247288 0.029636 0.559778 0.033 Uiso 1 1 calc R U . . .
H9B H 0.143846 -0.022828 0.481059 0.033 Uiso 1 1 calc R U . . .
H9C H 0.091563 0.074673 0.556358 0.033 Uiso 1 1 calc R U . . .
C10 C 0.1971(2) 0.03733(15) 0.28575(13) 0.0247(4) Uani 1 1 d . . . . .
H10A H 0.122590 0.056918 0.241117 0.037 Uiso 1 1 calc R U . . .
H10B H 0.171919 -0.032982 0.323303 0.037 Uiso 1 1 calc R U . . .
H10C H 0.281123 0.021055 0.249248 0.037 Uiso 1 1 calc R U . . .
C11 C 0.25090(18) 0.31551(14) 0.57242(11) 0.0193(3) Uani 1 1 d . . . . .
H11 H 0.284522 0.398541 0.562996 0.023 Uiso 1 1 calc R U . . .
C12 C 0.1095(2) 0.3252(2) 0.61768(13) 0.0291(4) Uani 1 1 d . . . . .
H12A H 0.047913 0.367653 0.573825 0.044 Uiso 1 1 calc R U . . .
H12B H 0.116241 0.368739 0.678573 0.044 Uiso 1 1 calc R U . . .
H12C H 0.073198 0.245535 0.629883 0.044 Uiso 1 1 calc R U . . .
C13 C 0.3556(2) 0.25394(18) 0.63655(13) 0.0266(4) Uani 1 1 d . . . . .
H13A H 0.368440 0.300210 0.695584 0.040 Uiso 1 1 calc R U . . .
H13B H 0.443217 0.247558 0.602335 0.040 Uiso 1 1 calc R U . . .
H13C H 0.322411 0.174384 0.653035 0.040 Uiso 1 1 calc R U . . .
C14 C 0.2712(2) 0.28863(15) 0.21720(12) 0.0220(3) Uani 1 1 d . . . . .
H14 H 0.255450 0.216332 0.176962 0.026 Uiso 1 1 calc R U . . .
C15 C 0.4129(2) 0.3357(2) 0.19176(14) 0.0317(4) Uani 1 1 d . . . . .
H15A H 0.431458 0.407785 0.229069 0.048 Uiso 1 1 calc R U . . .
H15B H 0.416482 0.354281 0.122887 0.048 Uiso 1 1 calc R U . . .
H15C H 0.482206 0.275508 0.206923 0.048 Uiso 1 1 calc R U . . .
C16 C 0.1571(2) 0.37620(16) 0.19329(13) 0.0243(4) Uani 1 1 d . . . . .
H16A H 0.173709 0.451159 0.227101 0.036 Uiso 1 1 calc R U . . .
H16B H 0.068638 0.343255 0.213672 0.036 Uiso 1 1 calc R U . . .
H16C H 0.155493 0.390519 0.123729 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.343(2) . ?
N1 C5 1.343(2) . ?
N2 C3 1.348(2) . ?
N2 C6 1.337(2) . ?
N3 C6 1.367(2) . ?
N3 C7 1.4091(19) . ?
N3 C11 1.4740(19) . ?
N4 C6 1.357(2) . ?
N4 C8 1.398(2) . ?
N4 C14 1.484(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.377(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.416(2) . ?
C3 C4 1.422(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.357(2) . ?
C7 C9 1.490(2) . ?
C8 C10 1.491(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.518(2) . ?
C11 C13 1.521(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 1.0000 . ?
C14 C15 1.521(3) . ?
C14 C16 1.523(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C5 N1 C1 114.65(14) . . ?
C6 N2 C3 123.21(14) . . ?
C6 N3 C7 109.53(12) . . ?
C6 N3 C11 120.86(13) . . ?
C7 N3 C11 129.58(13) . . ?
C6 N4 C8 109.43(13) . . ?
C6 N4 C14 124.40(13) . . ?
C8 N4 C14 125.77(14) . . ?
N1 C1 H1 117.3 . . ?
N1 C1 C2 125.36(15) . . ?
C2 C1 H1 117.3 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.15(15) . . ?
C3 C2 H2 119.9 . . ?
N2 C3 C2 118.70(14) . . ?
N2 C3 C4 126.46(14) . . ?
C2 C3 C4 114.74(14) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.69(14) . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 125.37(15) . . ?
N1 C5 H5 117.3 . . ?
C4 C5 H5 117.3 . . ?
N2 C6 N3 127.55(15) . . ?
N2 C6 N4 124.91(15) . . ?
N4 C6 N3 106.72(13) . . ?
N3 C7 C9 125.09(14) . . ?
C8 C7 N3 106.36(13) . . ?
C8 C7 C9 128.55(15) . . ?
N4 C8 C10 122.63(14) . . ?
C7 C8 N4 107.95(14) . . ?
C7 C8 C10 129.41(15) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 H11 106.5 . . ?
N3 C11 C12 111.27(14) . . ?
N3 C11 C13 112.09(14) . . ?
C12 C11 H11 106.5 . . ?
C12 C11 C13 113.46(15) . . ?
C13 C11 H11 106.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14 107.1 . . ?
N4 C14 C15 112.25(15) . . ?
N4 C14 C16 110.29(14) . . ?
C15 C14 H14 107.1 . . ?
C15 C14 C16 112.69(15) . . ?
C16 C14 H14 107.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 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
N1 C1 C2 C3 1.0(3) . . . . ?
N2 C3 C4 C5 -174.30(15) . . . . ?
N3 C7 C8 N4 0.32(18) . . . . ?
N3 C7 C8 C10 -179.87(16) . . . . ?
C1 N1 C5 C4 -0.2(3) . . . . ?
C1 C2 C3 N2 174.62(15) . . . . ?
C1 C2 C3 C4 -2.1(2) . . . . ?
C2 C3 C4 C5 2.1(2) . . . . ?
C3 N2 C6 N3 -77.5(2) . . . . ?
C3 N2 C6 N4 114.19(19) . . . . ?
C3 C4 C5 N1 -1.0(3) . . . . ?
C5 N1 C1 C2 0.2(3) . . . . ?
C6 N2 C3 C2 170.82(15) . . . . ?
C6 N2 C3 C4 -12.9(3) . . . . ?
C6 N3 C7 C8 -0.68(18) . . . . ?
C6 N3 C7 C9 179.69(16) . . . . ?
C6 N3 C11 C12 113.91(17) . . . . ?
C6 N3 C11 C13 -117.84(17) . . . . ?
C6 N4 C8 C7 0.15(18) . . . . ?
C6 N4 C8 C10 -179.68(15) . . . . ?
C6 N4 C14 C15 63.4(2) . . . . ?
C6 N4 C14 C16 -63.1(2) . . . . ?
C7 N3 C6 N2 -169.21(15) . . . . ?
C7 N3 C6 N4 0.77(17) . . . . ?
C7 N3 C11 C12 -68.3(2) . . . . ?
C7 N3 C11 C13 60.0(2) . . . . ?
C8 N4 C6 N2 169.74(15) . . . . ?
C8 N4 C6 N3 -0.57(17) . . . . ?
C8 N4 C14 C15 -124.54(18) . . . . ?
C8 N4 C14 C16 108.90(18) . . . . ?
C9 C7 C8 N4 179.92(16) . . . . ?
C9 C7 C8 C10 -0.3(3) . . . . ?
C11 N3 C6 N2 9.0(2) . . . . ?
C11 N3 C6 N4 179.00(14) . . . . ?
C11 N3 C7 C8 -178.71(15) . . . . ?
C11 N3 C7 C9 1.7(3) . . . . ?
C14 N4 C6 N2 -17.1(2) . . . . ?
C14 N4 C6 N3 172.60(14) . . . . ?
C14 N4 C8 C7 -172.90(15) . . . . ?
C14 N4 C8 C10 7.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_2
_database_code_depnum_ccdc_archive 'CCDC 2354125'
loop_
_audit_author_name
_audit_author_address
'Michael Seidl'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_audit_creation_date             2024-05-08
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H26 N4'
_chemical_formula_sum            'C16 H26 N4'
_chemical_formula_weight         274.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   6.2718(2)
_cell_length_b                   13.4687(6)
_cell_length_c                   18.5555(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.4840(10)
_cell_angle_gamma                90
_cell_volume                     1566.91(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6555
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.20
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7137
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1002 before and 0.0631 after correction.
The Ratio of minimum to maximum transmission is 0.9572.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   'Blessing, 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38299
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         2.196
_diffrn_ambient_temperature      173.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2890
_reflns_number_total             3589
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker Apex4 suite, 2021'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3589
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.6389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1186
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C6(H6A,H6B,H6C), C5(H5A,H5B,H5C), C9(H9A,H9B,H9C),
 C11(H11A,H11B,H11C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.58409(18) 0.74892(9) 0.61685(6) 0.0251(3) Uani 1 1 d . . . . .
N1 N 0.29365(18) 0.66178(9) 0.66792(6) 0.0257(3) Uani 1 1 d . . . . .
N3 N 0.58359(18) 0.58277(9) 0.61161(6) 0.0248(3) Uani 1 1 d . . . . .
N4 N 0.1919(2) 0.67429(11) 0.89109(7) 0.0344(3) Uani 1 1 d . . . . .
C12 C 0.2684(2) 0.66935(10) 0.73943(7) 0.0223(3) Uani 1 1 d . . . . .
C1 C 0.4806(2) 0.66448(10) 0.63596(7) 0.0223(3) Uani 1 1 d . . . . .
C13 C 0.0615(2) 0.66693(10) 0.76762(7) 0.0247(3) Uani 1 1 d . . . . .
H13 H -0.059569 0.664176 0.735824 0.030 Uiso 1 1 calc R U . . .
C16 C 0.4344(2) 0.67849(12) 0.79199(8) 0.0295(3) Uani 1 1 d . . . . .
H16 H 0.578152 0.683769 0.777543 0.035 Uiso 1 1 calc R U . . .
C14 C 0.0345(2) 0.66856(11) 0.84086(8) 0.0288(3) Uani 1 1 d . . . . .
H14 H -0.107455 0.665364 0.857336 0.035 Uiso 1 1 calc R U . . .
C3 C 0.7892(2) 0.61246(12) 0.58202(8) 0.0279(3) Uani 1 1 d . . . . .
H3A H 0.815414 0.577810 0.536036 0.033 Uiso 1 1 calc R U . . .
H3B H 0.908339 0.598294 0.616525 0.033 Uiso 1 1 calc R U . . .
C17 C 0.4779(2) 0.84746(11) 0.60464(8) 0.0281(3) Uani 1 1 d . . . . .
C2 C 0.7627(2) 0.72256(12) 0.57040(8) 0.0306(3) Uani 1 1 d . . . . .
H2A H 0.893966 0.758874 0.585115 0.037 Uiso 1 1 calc R U . . .
H2B H 0.727705 0.737556 0.519218 0.037 Uiso 1 1 calc R U . . .
C8 C 0.5455(2) 0.47740(11) 0.63320(8) 0.0273(3) Uani 1 1 d . . . . .
C15 C 0.3880(2) 0.67975(13) 0.86409(8) 0.0350(4) Uani 1 1 d . . . . .
H15 H 0.504673 0.684936 0.897558 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6375(3) 0.45861(13) 0.70888(9) 0.0382(4) Uani 1 1 d . . . . .
H10A H 0.788549 0.477356 0.710823 0.057 Uiso 1 1 calc R U . . .
H10B H 0.623600 0.388034 0.720708 0.057 Uiso 1 1 calc R U . . .
H10C H 0.559547 0.498368 0.743726 0.057 Uiso 1 1 calc R U . . .
C6 C 0.3269(3) 0.83955(13) 0.53863(8) 0.0357(4) Uani 1 1 d . . . . .
H6A H 0.409874 0.826176 0.495658 0.053 Uiso 1 1 calc R U . . .
H6B H 0.248891 0.902096 0.532233 0.053 Uiso 1 1 calc R U . . .
H6C H 0.225503 0.785305 0.545787 0.053 Uiso 1 1 calc R U . . .
C5 C 0.3563(3) 0.88113(12) 0.67070(9) 0.0378(4) Uani 1 1 d . . . . .
H5A H 0.226101 0.841497 0.674721 0.057 Uiso 1 1 calc R U . . .
H5B H 0.318453 0.951414 0.665578 0.057 Uiso 1 1 calc R U . . .
H5C H 0.446419 0.872047 0.714131 0.057 Uiso 1 1 calc R U . . .
C9 C 0.3070(2) 0.45213(12) 0.63006(10) 0.0367(4) Uani 1 1 d . . . . .
H9A H 0.235858 0.485184 0.669886 0.055 Uiso 1 1 calc R U . . .
H9B H 0.288619 0.380123 0.634223 0.055 Uiso 1 1 calc R U . . .
H9C H 0.244170 0.474946 0.584080 0.055 Uiso 1 1 calc R U . . .
C11 C 0.6575(3) 0.41063(12) 0.57924(9) 0.0386(4) Uani 1 1 d . . . . .
H11A H 0.607871 0.427272 0.530194 0.058 Uiso 1 1 calc R U . . .
H11B H 0.624236 0.341001 0.589383 0.058 Uiso 1 1 calc R U . . .
H11C H 0.811965 0.420848 0.583565 0.058 Uiso 1 1 calc R U . . .
C7 C 0.6520(3) 0.92378(13) 0.59009(10) 0.0423(4) Uani 1 1 d . . . . .
H7A H 0.755649 0.924438 0.630538 0.063 Uiso 1 1 calc R U . . .
H7B H 0.587700 0.989753 0.584679 0.063 Uiso 1 1 calc R U . . .
H7C H 0.724435 0.906058 0.545712 0.063 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C1 1.3609(18) . ?
N2 C17 1.4997(19) . ?
N2 C2 1.4743(17) . ?
N1 C12 1.3443(17) . ?
N1 C1 1.3284(17) . ?
N3 C1 1.3591(18) . ?
N3 C3 1.4700(17) . ?
N3 C8 1.4955(18) . ?
N4 C14 1.342(2) . ?
N4 C15 1.3420(19) . ?
C12 C13 1.4119(18) . ?
C12 C16 1.4136(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3740(19) . ?
C16 H16 0.9500 . ?
C16 C15 1.376(2) . ?
C14 H14 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.507(2) . ?
C17 C6 1.532(2) . ?
C17 C5 1.529(2) . ?
C17 C7 1.529(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C8 C10 1.525(2) . ?
C8 C9 1.534(2) . ?
C8 C11 1.530(2) . ?
C15 H15 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C17 124.47(11) . . ?
C1 N2 C2 109.00(11) . . ?
C2 N2 C17 117.79(11) . . ?
C1 N1 C12 124.52(12) . . ?
C1 N3 C3 109.44(11) . . ?
C1 N3 C8 126.79(11) . . ?
C3 N3 C8 120.39(11) . . ?
C15 N4 C14 114.11(12) . . ?
N1 C12 C13 119.80(12) . . ?
N1 C12 C16 125.73(12) . . ?
C13 C12 C16 114.46(12) . . ?
N1 C1 N2 124.86(13) . . ?
N1 C1 N3 123.97(13) . . ?
N3 C1 N2 110.87(11) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.25(13) . . ?
C14 C13 H13 119.9 . . ?
C12 C16 H16 120.0 . . ?
C15 C16 C12 120.08(13) . . ?
C15 C16 H16 120.0 . . ?
N4 C14 C13 125.50(13) . . ?
N4 C14 H14 117.2 . . ?
C13 C14 H14 117.2 . . ?
N3 C3 H3A 111.1 . . ?
N3 C3 H3B 111.1 . . ?
N3 C3 C2 103.09(11) . . ?
H3A C3 H3B 109.1 . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
N2 C17 C6 108.78(12) . . ?
N2 C17 C5 111.73(12) . . ?
N2 C17 C7 107.75(12) . . ?
C5 C17 C6 110.55(13) . . ?
C5 C17 C7 108.40(13) . . ?
C7 C17 C6 109.57(13) . . ?
N2 C2 C3 103.65(11) . . ?
N2 C2 H2A 111.0 . . ?
N2 C2 H2B 111.0 . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
N3 C8 C10 110.17(12) . . ?
N3 C8 C9 111.27(12) . . ?
N3 C8 C11 107.66(12) . . ?
C10 C8 C9 110.09(13) . . ?
C10 C8 C11 109.63(13) . . ?
C11 C8 C9 107.96(13) . . ?
N4 C15 C16 125.52(14) . . ?
N4 C15 H15 117.2 . . ?
C16 C15 H15 117.2 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C17 C6 H6A 109.5 . . ?
C17 C6 H6B 109.5 . . ?
C17 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C17 C5 H5A 109.5 . . ?
C17 C5 H5B 109.5 . . ?
C17 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C7 H7A 109.5 . . ?
C17 C7 H7B 109.5 . . ?
C17 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
N1 C12 C13 C14 176.05(13) . . . . ?
N1 C12 C16 C15 -176.15(15) . . . . ?
N3 C3 C2 N2 19.27(14) . . . . ?
C12 N1 C1 N2 -84.83(18) . . . . ?
C12 N1 C1 N3 102.00(17) . . . . ?
C12 C13 C14 N4 1.3(2) . . . . ?
C12 C16 C15 N4 -1.0(3) . . . . ?
C1 N2 C17 C6 -65.72(16) . . . . ?
C1 N2 C17 C5 56.60(18) . . . . ?
C1 N2 C17 C7 175.57(13) . . . . ?
C1 N2 C2 C3 -15.62(15) . . . . ?
C1 N1 C12 C13 179.11(13) . . . . ?
C1 N1 C12 C16 -1.9(2) . . . . ?
C1 N3 C3 C2 -17.46(14) . . . . ?
C1 N3 C8 C10 -74.06(17) . . . . ?
C1 N3 C8 C9 48.33(18) . . . . ?
C1 N3 C8 C11 166.44(13) . . . . ?
C13 C12 C16 C15 2.9(2) . . . . ?
C16 C12 C13 C14 -3.1(2) . . . . ?
C14 N4 C15 C16 -0.9(2) . . . . ?
C3 N3 C1 N2 8.27(15) . . . . ?
C3 N3 C1 N1 -177.73(12) . . . . ?
C3 N3 C8 C10 82.91(15) . . . . ?
C3 N3 C8 C9 -154.71(13) . . . . ?
C3 N3 C8 C11 -36.60(17) . . . . ?
C17 N2 C1 N1 -22.3(2) . . . . ?
C17 N2 C1 N3 151.63(12) . . . . ?
C17 N2 C2 C3 -164.73(11) . . . . ?
C2 N2 C1 N1 -168.87(12) . . . . ?
C2 N2 C1 N3 5.07(15) . . . . ?
C2 N2 C17 C6 78.20(15) . . . . ?
C2 N2 C17 C5 -159.48(13) . . . . ?
C2 N2 C17 C7 -40.51(17) . . . . ?
C8 N3 C1 N2 167.30(12) . . . . ?
C8 N3 C1 N1 -18.7(2) . . . . ?
C8 N3 C3 C2 -178.05(12) . . . . ?
C15 N4 C14 C13 0.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_3
_database_code_depnum_ccdc_archive 'CCDC 2354126'
loop_
_audit_author_name
_audit_author_address
'Michael Seidl'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_audit_creation_date             2024-05-08
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(B F4), C27 H43 N6'
_chemical_formula_sum            'C27 H43 B2 F8 N6'
_chemical_formula_weight         625.29
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.6898(5)
_cell_length_b                   8.5225(3)
_cell_length_c                   24.0701(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3218.57(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.123
_cell_measurement_theta_min      2.849
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
? was used for absorption correction.
wR2(int) was 0.1176 before and 0.0804 after correction.
The Ratio of minimum to maximum transmission is 0.8355.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1316
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            35131
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.294
_diffrn_reflns_theta_min         3.204
_diffrn_ambient_temperature      100.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.944
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                7136
_reflns_number_total             7933
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_collection       'Bruker Apex III'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         7933
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0631
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1098P)²+1.4149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1775
_refine_ls_wR_factor_ref         0.1827
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7(10)
 0.3(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(B3) \\sim Ueq, Uanis(F9) \\sim Ueq: with sigma of 0.006 and sigma for
terminal atoms of 0.01
Uanis(F10) \\sim Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.008
4. Others
 Sof(F9)=Sof(F10)=Sof(F11)=Sof(F12)=Sof(B3)=1-FVAR(1)
 Sof(F5)=Sof(F6)=Sof(F7)=Sof(F8)=Sof(B2)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C11(H11), C22(H22), C25(H25)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
5.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C21(H21A,
 H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C),
 C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F9 F 0.4084(17) 0.724(4) 0.3742(14) 0.027(5) Uani 0.196(8) 1 d . U P A 2
F10 F 0.3338(11) 0.717(2) 0.2935(6) 0.052(5) Uani 0.196(8) 1 d . U P A 2
F11 F 0.3805(10) 0.9443(12) 0.3292(6) 0.027(3) Uani 0.196(8) 1 d . . P A 2
F12 F 0.2729(11) 0.820(2) 0.3717(7) 0.058(5) Uani 0.196(8) 1 d . . P A 2
B3 B 0.346(2) 0.810(4) 0.3426(14) 0.030(8) Uani 0.196(8) 1 d . U P A 2
F5 F 0.4329(5) 0.7315(12) 0.3681(4) 0.0376(16) Uani 0.804(8) 1 d . . P A 1
F6 F 0.3050(3) 0.6613(5) 0.3301(2) 0.0593(13) Uani 0.804(8) 1 d . . P A 1
F7 F 0.4020(2) 0.7880(7) 0.27810(14) 0.0617(14) Uani 0.804(8) 1 d . . P A 1
F8 F 0.3326(4) 0.9156(6) 0.3465(2) 0.0612(17) Uani 0.804(8) 1 d . . P A 1
B2 B 0.3677(5) 0.7749(9) 0.3317(3) 0.0257(13) Uani 0.804(8) 1 d . . P A 1
F1 F 0.5340(2) 0.9373(4) 0.61811(15) 0.0557(8) Uani 1 1 d . . . . .
F2 F 0.43164(16) 0.7827(3) 0.58082(12) 0.0418(6) Uani 1 1 d . . . . .
F3 F 0.5447(2) 0.6693(4) 0.62396(17) 0.0625(10) Uani 1 1 d . . . . .
F4 F 0.4431(2) 0.7998(4) 0.67451(13) 0.0531(8) Uani 1 1 d . . . . .
B1 B 0.4886(3) 0.7980(6) 0.6243(2) 0.0403(10) Uani 1 1 d . . . . .
N1 N 0.74897(18) 0.4287(3) 0.67482(11) 0.0208(5) Uani 1 1 d . . . . .
N2 N 0.6852(2) 0.2898(4) 0.51649(12) 0.0262(6) Uani 1 1 d . . . . .
N3 N 0.54663(19) 0.1926(3) 0.49123(11) 0.0207(5) Uani 1 1 d . . . . .
N4 N 0.6453(2) 0.0172(4) 0.50352(14) 0.0277(6) Uani 1 1 d . . . . .
N5 N 0.74143(19) 0.6018(4) 0.75438(12) 0.0241(6) Uani 1 1 d . . . . .
N6 N 0.8443(2) 0.4297(4) 0.75494(13) 0.0295(7) Uani 1 1 d . . . . .
C1 C 0.7836(2) 0.5004(4) 0.62872(15) 0.0236(6) Uani 1 1 d . . . . .
H1 H 0.823912 0.582467 0.633339 0.028 Uiso 1 1 calc R U . . .
C2 C 0.7608(2) 0.4552(4) 0.57719(14) 0.0240(6) Uani 1 1 d . . . . .
H2 H 0.784988 0.507264 0.546044 0.029 Uiso 1 1 calc R U . . .
C3 C 0.7012(2) 0.3307(4) 0.56820(13) 0.0211(6) Uani 1 1 d . . . . .
C4 C 0.6649(2) 0.2628(4) 0.61758(14) 0.0217(6) Uani 1 1 d . . . . .
H4 H 0.623480 0.182056 0.614238 0.026 Uiso 1 1 calc R U . . .
C5 C 0.6890(2) 0.3122(4) 0.66890(13) 0.0210(6) Uani 1 1 d . . . . .
H5 H 0.664149 0.265868 0.700958 0.025 Uiso 1 1 calc R U . . .
C6 C 0.6281(2) 0.1706(4) 0.50628(13) 0.0230(6) Uani 1 1 d . . . . .
C7 C 0.5099(2) 0.0470(4) 0.47985(13) 0.0233(6) Uani 1 1 d . . . . .
C8 C 0.5712(3) -0.0622(4) 0.48764(15) 0.0285(7) Uani 1 1 d . . . . .
C9 C 0.4193(3) 0.0251(5) 0.46229(17) 0.0322(8) Uani 1 1 d . . . . .
H9A H 0.382636 0.095741 0.483718 0.048 Uiso 1 1 calc R U . . .
H9B H 0.402154 -0.083827 0.469015 0.048 Uiso 1 1 calc R U . . .
H9C H 0.413851 0.048960 0.422627 0.048 Uiso 1 1 calc R U . . .
C10 C 0.5644(3) -0.2361(5) 0.4811(2) 0.0416(10) Uani 1 1 d . . . . .
H10A H 0.595514 -0.268829 0.447729 0.062 Uiso 1 1 calc R U . . .
H10B H 0.504332 -0.265779 0.477506 0.062 Uiso 1 1 calc R U . . .
H10C H 0.589013 -0.287802 0.513739 0.062 Uiso 1 1 calc R U . . .
C11 C 0.5087(2) 0.3515(4) 0.48877(15) 0.0273(7) Uani 1 1 d . . . . .
H11 H 0.557255 0.427049 0.491543 0.033 Uiso 1 1 calc R U . . .
C12 C 0.4663(4) 0.3830(5) 0.4337(2) 0.0440(11) Uani 1 1 d . . . . .
H12A H 0.414254 0.319888 0.430757 0.066 Uiso 1 1 calc R U . . .
H12B H 0.505293 0.355068 0.403486 0.066 Uiso 1 1 calc R U . . .
H12C H 0.451684 0.494563 0.431050 0.066 Uiso 1 1 calc R U . . .
C13 C 0.4530(3) 0.3804(5) 0.53938(17) 0.0366(9) Uani 1 1 d . . . . .
H13A H 0.433509 0.489610 0.539363 0.055 Uiso 1 1 calc R U . . .
H13B H 0.486011 0.360029 0.573190 0.055 Uiso 1 1 calc R U . . .
H13C H 0.403592 0.310119 0.538233 0.055 Uiso 1 1 calc R U . . .
C14 C 0.7325(3) -0.0430(6) 0.5151(2) 0.0442(10) Uani 1 1 d . . . . .
C15 C 0.7667(4) -0.1420(8) 0.4691(3) 0.0639(16) Uani 1 1 d . . . . .
H15A H 0.736024 -0.242122 0.468053 0.096 Uiso 1 1 calc R U . . .
H15B H 0.827527 -0.161761 0.475353 0.096 Uiso 1 1 calc R U . . .
H15C H 0.759210 -0.087263 0.433621 0.096 Uiso 1 1 calc R U . . .
C16 C 0.7381(4) -0.1157(6) 0.5712(3) 0.0513(12) Uani 1 1 d . . . . .
H16A H 0.727287 -0.035738 0.599596 0.077 Uiso 1 1 calc R U . . .
H16B H 0.795147 -0.159902 0.576551 0.077 Uiso 1 1 calc R U . . .
H16C H 0.695478 -0.199331 0.574388 0.077 Uiso 1 1 calc R U . . .
C17 C 0.7763(2) 0.4808(4) 0.72765(13) 0.0230(6) Uani 1 1 d . . . . .
C18 C 0.7894(3) 0.6295(5) 0.80219(15) 0.0314(8) Uani 1 1 d . . . . .
C19 C 0.8532(3) 0.5240(5) 0.80155(16) 0.0337(8) Uani 1 1 d . . . . .
C20 C 0.7684(3) 0.7494(6) 0.84532(19) 0.0438(10) Uani 1 1 d . . . . .
H20A H 0.816062 0.758605 0.871473 0.066 Uiso 1 1 calc R U . . .
H20B H 0.717005 0.717238 0.865417 0.066 Uiso 1 1 calc R U . . .
H20C H 0.758511 0.850972 0.827387 0.066 Uiso 1 1 calc R U . . .
C21 C 0.9229(3) 0.5037(7) 0.8426(2) 0.0510(12) Uani 1 1 d . . . . .
H21A H 0.921349 0.396636 0.857451 0.076 Uiso 1 1 calc R U . . .
H21B H 0.915416 0.578849 0.873043 0.076 Uiso 1 1 calc R U . . .
H21C H 0.977880 0.522143 0.824468 0.076 Uiso 1 1 calc R U . . .
C22 C 0.6643(2) 0.6871(4) 0.73415(15) 0.0278(7) Uani 1 1 d . . . . .
H22 H 0.647320 0.637901 0.698103 0.033 Uiso 1 1 calc R U . . .
C23 C 0.5901(3) 0.6681(6) 0.7736(2) 0.0430(10) Uani 1 1 d . . . . .
H23A H 0.577981 0.556245 0.778786 0.065 Uiso 1 1 calc R U . . .
H23B H 0.539723 0.720218 0.758103 0.065 Uiso 1 1 calc R U . . .
H23C H 0.604364 0.715537 0.809506 0.065 Uiso 1 1 calc R U . . .
C24 C 0.6861(3) 0.8584(5) 0.7220(2) 0.0419(10) Uani 1 1 d . . . . .
H24A H 0.640932 0.905039 0.699245 0.063 Uiso 1 1 calc R U . . .
H24B H 0.740350 0.863792 0.701990 0.063 Uiso 1 1 calc R U . . .
H24C H 0.690861 0.916200 0.757086 0.063 Uiso 1 1 calc R U . . .
C25 C 0.8988(3) 0.2912(5) 0.74276(19) 0.0383(9) Uani 1 1 d . . . . .
H25 H 0.953627 0.312057 0.762612 0.046 Uiso 1 1 calc R U . . .
C26 C 0.9229(4) 0.2714(7) 0.6838(3) 0.0585(15) Uani 1 1 d . . . . .
H26A H 0.871878 0.248152 0.661812 0.088 Uiso 1 1 calc R U . . .
H26B H 0.963556 0.184728 0.680385 0.088 Uiso 1 1 calc R U . . .
H26C H 0.949167 0.368382 0.670186 0.088 Uiso 1 1 calc R U . . .
C27 C 0.8618(4) 0.1498(7) 0.7710(3) 0.0595(15) Uani 1 1 d . . . . .
H27A H 0.851633 0.173712 0.810320 0.089 Uiso 1 1 calc R U . . .
H27B H 0.901741 0.061815 0.768084 0.089 Uiso 1 1 calc R U . . .
H27C H 0.807763 0.121508 0.753214 0.089 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F9 B3 1.44(5) . ?
F10 B3 1.44(4) . ?
F11 B3 1.30(4) . ?
F12 B3 1.35(4) . ?
F5 B2 1.397(11) . ?
F6 B2 1.381(7) . ?
F7 B2 1.402(9) . ?
F8 B2 1.367(9) . ?
F1 B1 1.392(6) . ?
F2 B1 1.381(6) . ?
F3 B1 1.406(5) . ?
F4 B1 1.405(7) . ?
N1 C1 1.378(4) . ?
N1 C5 1.376(4) . ?
N1 C17 1.414(4) . ?
N2 C3 1.317(4) . ?
N2 C6 1.377(5) . ?
N3 C6 1.341(5) . ?
N3 C7 1.396(4) . ?
N3 C11 1.480(4) . ?
N4 C6 1.337(4) . ?
N4 C8 1.399(5) . ?
N4 C14 1.486(5) . ?
N5 C17 1.333(5) . ?
N5 C18 1.395(4) . ?
N5 C22 1.493(5) . ?
N6 C17 1.326(5) . ?
N6 C19 1.387(5) . ?
N6 C25 1.487(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.347(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.432(5) . ?
C3 C4 1.439(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.358(5) . ?
C5 H5 0.9500 . ?
C7 C8 1.351(5) . ?
C7 C9 1.494(5) . ?
C8 C10 1.494(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.508(6) . ?
C11 C13 1.519(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.493(8) . ?
C14 C16 1.488(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 C19 1.345(6) . ?
C18 C20 1.494(6) . ?
C19 C21 1.484(6) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 1.0000 . ?
C22 C23 1.512(6) . ?
C22 C24 1.527(6) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25 1.0000 . ?
C25 C26 1.478(7) . ?
C25 C27 1.501(7) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
F10 B3 F9 104(3) . . ?
F11 B3 F9 108(3) . . ?
F11 B3 F10 110(3) . . ?
F11 B3 F12 115(3) . . ?
F12 B3 F9 109(3) . . ?
F12 B3 F10 110(3) . . ?
F5 B2 F7 108.5(7) . . ?
F6 B2 F5 110.7(6) . . ?
F6 B2 F7 107.7(6) . . ?
F8 B2 F5 111.3(7) . . ?
F8 B2 F6 109.6(8) . . ?
F8 B2 F7 109.0(5) . . ?
F1 B1 F3 110.2(4) . . ?
F1 B1 F4 110.0(4) . . ?
F2 B1 F1 109.3(4) . . ?
F2 B1 F3 109.1(4) . . ?
F2 B1 F4 108.9(4) . . ?
F4 B1 F3 109.3(5) . . ?
C1 N1 C17 117.7(3) . . ?
C5 N1 C1 120.4(3) . . ?
C5 N1 C17 121.8(3) . . ?
C3 N2 C6 119.2(3) . . ?
C6 N3 C7 108.8(3) . . ?
C6 N3 C11 121.5(3) . . ?
C7 N3 C11 129.8(3) . . ?
C6 N4 C8 108.5(3) . . ?
C6 N4 C14 121.0(3) . . ?
C8 N4 C14 130.5(3) . . ?
C17 N5 C18 107.9(3) . . ?
C17 N5 C22 123.5(3) . . ?
C18 N5 C22 128.6(3) . . ?
C17 N6 C19 106.9(3) . . ?
C17 N6 C25 128.7(3) . . ?
C19 N6 C25 124.2(3) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 N1 120.7(3) . . ?
C2 C1 H1 119.7 . . ?
C1 C2 H2 119.2 . . ?
C1 C2 C3 121.6(3) . . ?
C3 C2 H2 119.2 . . ?
N2 C3 C2 117.6(3) . . ?
N2 C3 C4 126.8(3) . . ?
C2 C3 C4 115.6(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.4 . . ?
N1 C5 H5 119.7 . . ?
C4 C5 N1 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
N3 C6 N2 124.5(3) . . ?
N4 C6 N2 126.7(3) . . ?
N4 C6 N3 108.5(3) . . ?
N3 C7 C9 124.0(3) . . ?
C8 C7 N3 107.0(3) . . ?
C8 C7 C9 129.0(3) . . ?
N4 C8 C10 124.6(4) . . ?
C7 C8 N4 107.2(3) . . ?
C7 C8 C10 128.2(4) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 H11 106.3 . . ?
N3 C11 C12 112.1(3) . . ?
N3 C11 C13 110.3(3) . . ?
C12 C11 H11 106.3 . . ?
C12 C11 C13 115.0(4) . . ?
C13 C11 H11 106.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 C15 112.8(5) . . ?
N4 C14 C16 111.6(4) . . ?
C16 C14 C15 114.6(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N5 C17 N1 123.6(3) . . ?
N6 C17 N1 125.9(3) . . ?
N6 C17 N5 110.2(3) . . ?
N5 C18 C20 124.7(4) . . ?
C19 C18 N5 106.2(3) . . ?
C19 C18 C20 129.0(4) . . ?
N6 C19 C21 123.0(4) . . ?
C18 C19 N6 108.8(3) . . ?
C18 C19 C21 128.2(4) . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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 . . ?
N5 C22 H22 107.1 . . ?
N5 C22 C23 111.6(3) . . ?
N5 C22 C24 110.3(3) . . ?
C23 C22 H22 107.1 . . ?
C23 C22 C24 113.2(4) . . ?
C24 C22 H22 107.1 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N6 C25 H25 105.0 . . ?
N6 C25 C27 109.0(4) . . ?
C26 C25 N6 115.3(4) . . ?
C26 C25 H25 105.0 . . ?
C26 C25 C27 116.3(5) . . ?
C27 C25 H25 105.0 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
N1 C1 C2 C3 -0.8(5) . . . . ?
N2 C3 C4 C5 177.7(3) . . . . ?
N3 C7 C8 N4 -0.3(4) . . . . ?
N3 C7 C8 C10 179.8(4) . . . . ?
N5 C18 C19 N6 -1.3(5) . . . . ?
N5 C18 C19 C21 179.3(5) . . . . ?
C1 N1 C5 C4 2.0(5) . . . . ?
C1 N1 C17 N5 86.1(4) . . . . ?
C1 N1 C17 N6 -86.4(4) . . . . ?
C1 C2 C3 N2 -177.2(3) . . . . ?
C1 C2 C3 C4 2.6(5) . . . . ?
C2 C3 C4 C5 -2.1(5) . . . . ?
C3 N2 C6 N3 99.9(4) . . . . ?
C3 N2 C6 N4 -88.0(5) . . . . ?
C3 C4 C5 N1 -0.1(5) . . . . ?
C5 N1 C1 C2 -1.6(5) . . . . ?
C5 N1 C17 N5 -92.9(4) . . . . ?
C5 N1 C17 N6 94.6(4) . . . . ?
C6 N2 C3 C2 -179.9(3) . . . . ?
C6 N2 C3 C4 0.3(5) . . . . ?
C6 N3 C7 C8 -0.8(4) . . . . ?
C6 N3 C7 C9 179.4(3) . . . . ?
C6 N3 C11 C12 128.0(4) . . . . ?
C6 N3 C11 C13 -102.5(4) . . . . ?
C6 N4 C8 C7 1.3(4) . . . . ?
C6 N4 C8 C10 -178.8(4) . . . . ?
C6 N4 C14 C15 -125.9(5) . . . . ?
C6 N4 C14 C16 103.4(5) . . . . ?
C7 N3 C6 N2 175.0(3) . . . . ?
C7 N3 C6 N4 1.6(4) . . . . ?
C7 N3 C11 C12 -52.2(5) . . . . ?
C7 N3 C11 C13 77.3(4) . . . . ?
C8 N4 C6 N2 -174.9(3) . . . . ?
C8 N4 C6 N3 -1.8(4) . . . . ?
C8 N4 C14 C15 52.4(7) . . . . ?
C8 N4 C14 C16 -78.3(6) . . . . ?
C9 C7 C8 N4 179.5(4) . . . . ?
C9 C7 C8 C10 -0.5(7) . . . . ?
C11 N3 C6 N2 -5.2(5) . . . . ?
C11 N3 C6 N4 -178.6(3) . . . . ?
C11 N3 C7 C8 179.4(3) . . . . ?
C11 N3 C7 C9 -0.4(5) . . . . ?
C14 N4 C6 N2 3.7(6) . . . . ?
C14 N4 C6 N3 176.8(3) . . . . ?
C14 N4 C8 C7 -177.2(4) . . . . ?
C14 N4 C8 C10 2.8(7) . . . . ?
C17 N1 C1 C2 179.4(3) . . . . ?
C17 N1 C5 C4 -179.0(3) . . . . ?
C17 N5 C18 C19 1.2(4) . . . . ?
C17 N5 C18 C20 -176.2(4) . . . . ?
C17 N5 C22 C23 115.5(4) . . . . ?
C17 N5 C22 C24 -117.8(4) . . . . ?
C17 N6 C19 C18 1.0(5) . . . . ?
C17 N6 C19 C21 -179.7(4) . . . . ?
C17 N6 C25 C26 44.9(7) . . . . ?
C17 N6 C25 C27 -87.9(6) . . . . ?
C18 N5 C17 N1 -174.1(3) . . . . ?
C18 N5 C17 N6 -0.6(4) . . . . ?
C18 N5 C22 C23 -64.5(5) . . . . ?
C18 N5 C22 C24 62.3(5) . . . . ?
C19 N6 C17 N1 173.2(3) . . . . ?
C19 N6 C17 N5 -0.2(4) . . . . ?
C19 N6 C25 C26 -140.5(5) . . . . ?
C19 N6 C25 C27 86.7(6) . . . . ?
C20 C18 C19 N6 176.0(4) . . . . ?
C20 C18 C19 C21 -3.4(8) . . . . ?
C22 N5 C17 N1 5.9(5) . . . . ?
C22 N5 C17 N6 179.4(3) . . . . ?
C22 N5 C18 C19 -178.8(4) . . . . ?
C22 N5 C18 C20 3.7(7) . . . . ?
C25 N6 C17 N1 -11.5(6) . . . . ?
C25 N6 C17 N5 175.1(4) . . . . ?
C25 N6 C19 C18 -174.6(4) . . . . ?
C25 N6 C19 C21 4.7(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7(10)
2 0.3(10)

####################################################################### 
# 
# 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_compound_6
_database_code_depnum_ccdc_archive 'CCDC 2354129'
loop_
_audit_author_name
_audit_author_address
'Michael Seidl'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_audit_creation_date             2024-05-08
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H48 Cl2 N8 Pd'
_chemical_formula_sum            'C32 H48 Cl2 N8 Pd'
_chemical_formula_weight         722.08
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.6684(2)
_cell_length_b                   13.6481(4)
_cell_length_c                   18.8863(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.5077(18)
_cell_angle_gamma                90
_cell_volume                     1695.25(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5230
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.671
_cell_measurement_theta_min      3.098
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
? was used for absorption correction.
wR2(int) was 0.1262 before and 0.0513 after correction.
The Ratio of minimum to maximum transmission is 0.9207.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24127
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.384
_diffrn_reflns_theta_min         3.179
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3437
_reflns_number_total             4236
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_collection       'Bruker Apex III'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4236
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0261P)²+1.5400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0744
_refine_special_details          ?
_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, All C(H,H,H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C14B) \\sim Ueq, Uanis(C15B) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.006
3. Others
 Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(H15D)=
 Sof(H15E)=Sof(H15F)=1-FVAR(1)
 Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=
 Sof(H15B)=Sof(H15C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C11(H11), C14A(H14A), C14B(H14B)
4.b Me refined with riding coordinates:
 C16(H16A,H16B,H16C), C16(H16D,H16E,H16F)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
4.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C15A(H15A,H15B,H15C), C15B(H15D,H15E,H15F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.000000 0.000000 0.000000 0.01848(7) Uani 1 2 d S . P . .
Cl1 Cl -0.21819(8) -0.10611(4) 0.04435(3) 0.02625(13) Uani 1 1 d . . . . .
N1 N 0.1540(3) 0.02234(13) 0.10026(10) 0.0205(4) Uani 1 1 d . . . . .
N2 N 0.4436(3) 0.05604(14) 0.31299(10) 0.0242(4) Uani 1 1 d . . . . .
N3 N 0.7484(3) -0.04660(13) 0.33519(9) 0.0195(4) Uani 1 1 d . . . . .
N4 N 0.7644(3) 0.10332(14) 0.37646(10) 0.0251(4) Uani 1 1 d . . . . .
C1 C 0.3574(3) 0.01447(15) 0.11670(11) 0.0199(4) Uani 1 1 d . . . . .
H1 H 0.432310 0.002133 0.078978 0.024 Uiso 1 1 calc R U . . .
C2 C 0.4621(3) 0.02341(15) 0.18539(11) 0.0203(4) Uani 1 1 d . . . . .
H2 H 0.605833 0.016516 0.193885 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3593(3) 0.04272(15) 0.24370(11) 0.0209(4) Uani 1 1 d . . . . .
C4 C 0.1454(4) 0.05333(16) 0.22433(12) 0.0238(5) Uani 1 1 d . . . . .
H4 H 0.065911 0.068125 0.260313 0.029 Uiso 1 1 calc R U . . .
C5 C 0.0526(3) 0.04261(17) 0.15500(12) 0.0235(5) Uani 1 1 d . . . . .
H5 H -0.090901 0.049731 0.144432 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6404(4) 0.03796(16) 0.33705(11) 0.0212(4) Uani 1 1 d . . . . .
C7 C 0.9447(3) -0.03309(17) 0.37378(12) 0.0233(5) Uani 1 1 d . . . . .
C8 C 0.9545(4) 0.06020(17) 0.39901(12) 0.0264(5) Uani 1 1 d . . . . .
C9 C 1.1103(4) -0.1067(2) 0.37878(14) 0.0332(6) Uani 1 1 d . . . . .
H9A H 1.063974 -0.168744 0.396680 0.050 Uiso 1 1 calc R U . . .
H9B H 1.229366 -0.083072 0.411804 0.050 Uiso 1 1 calc R U . . .
H9C H 1.146770 -0.117003 0.331148 0.050 Uiso 1 1 calc R U . . .
C10 C 1.1315(4) 0.1123(2) 0.44161(13) 0.0345(6) Uani 1 1 d . . . . .
H10A H 1.149497 0.175900 0.419476 0.052 Uiso 1 1 calc R U . . .
H10B H 1.254659 0.072781 0.442520 0.052 Uiso 1 1 calc R U . . .
H10C H 1.106439 0.122221 0.490792 0.052 Uiso 1 1 calc R U . . .
C11 C 0.6511(3) -0.14024(15) 0.30909(11) 0.0204(4) Uani 1 1 d . . . . .
H11 H 0.510218 -0.124072 0.284741 0.024 Uiso 1 1 calc R U . . .
C12 C 0.7579(4) -0.18878(17) 0.25323(12) 0.0271(5) Uani 1 1 d . . . . .
H12A H 0.773873 -0.141228 0.215681 0.041 Uiso 1 1 calc R U . . .
H12B H 0.676653 -0.244387 0.231843 0.041 Uiso 1 1 calc R U . . .
H12C H 0.892064 -0.212030 0.276131 0.041 Uiso 1 1 calc R U . . .
C13 C 0.6298(4) -0.20799(17) 0.37175(12) 0.0258(5) Uani 1 1 d . . . . .
H13A H 0.764123 -0.232626 0.393265 0.039 Uiso 1 1 calc R U . . .
H13B H 0.541374 -0.263240 0.354315 0.039 Uiso 1 1 calc R U . . .
H13C H 0.570163 -0.171598 0.407896 0.039 Uiso 1 1 calc R U . . .
C16 C 0.7854(4) 0.26775(18) 0.32715(13) 0.0304(5) Uani 1 1 d . . . . .
H16A H 0.756954 0.236615 0.279793 0.046 Uiso 0.799(8) 1 calc R U P A 1
H16B H 0.728294 0.334067 0.324176 0.046 Uiso 0.799(8) 1 calc R U P A 1
H16C H 0.932760 0.271223 0.343024 0.046 Uiso 0.799(8) 1 calc R U P A 1
H16D H 0.805143 0.335816 0.343323 0.046 Uiso 0.201(8) 1 calc R U P A 2
H16E H 0.894229 0.249012 0.300740 0.046 Uiso 0.201(8) 1 calc R U P A 2
H16F H 0.653639 0.261428 0.295668 0.046 Uiso 0.201(8) 1 calc R U P A 2
C14A C 0.6897(6) 0.2078(2) 0.38053(16) 0.0206(8) Uani 0.799(8) 1 d . . P A 1
H14A H 0.539807 0.207021 0.362838 0.025 Uiso 0.799(8) 1 calc R U P A 1
C15A C 0.7200(6) 0.2464(2) 0.45654(18) 0.0269(9) Uani 0.799(8) 1 d . . P A 1
H15A H 0.669215 0.198267 0.487784 0.040 Uiso 0.799(8) 1 calc R U P A 1
H15B H 0.645251 0.308044 0.457799 0.040 Uiso 0.799(8) 1 calc R U P A 1
H15C H 0.865088 0.257917 0.473333 0.040 Uiso 0.799(8) 1 calc R U P A 1
C14B C 0.790(2) 0.2032(8) 0.3898(6) 0.017(3) Uani 0.201(8) 1 d . U P A 2
H14B H 0.920975 0.213722 0.423305 0.020 Uiso 0.201(8) 1 calc R U P A 2
C15B C 0.616(2) 0.2292(9) 0.4279(7) 0.024(3) Uani 0.201(8) 1 d . U P A 2
H15D H 0.486989 0.211843 0.397520 0.035 Uiso 0.201(8) 1 calc R U P A 2
H15E H 0.618020 0.299710 0.437816 0.035 Uiso 0.201(8) 1 calc R U P A 2
H15F H 0.628968 0.192922 0.473244 0.035 Uiso 0.201(8) 1 calc R U P A 2


_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 2.3061(5) 3 ?
Pd1 Cl1 2.3061(5) . ?
Pd1 N1 2.0225(18) 3 ?
Pd1 N1 2.0225(18) . ?
N1 C1 1.345(3) . ?
N1 C5 1.354(3) . ?
N2 C3 1.349(3) . ?
N2 C6 1.339(3) . ?
N3 C6 1.364(3) . ?
N3 C7 1.401(3) . ?
N3 C11 1.481(3) . ?
N4 C6 1.353(3) . ?
N4 C8 1.399(3) . ?
N4 C14A 1.517(4) . ?
N4 C14B 1.392(12) . ?
C1 H1 0.9500 . ?
C1 C2 1.373(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.415(3) . ?
C3 C4 1.420(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.361(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.357(3) . ?
C7 C9 1.484(3) . ?
C8 C10 1.494(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.519(3) . ?
C11 C13 1.527(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16D 0.9800 . ?
C16 H16E 0.9800 . ?
C16 H16F 0.9800 . ?
C16 C14A 1.518(4) . ?
C16 C14B 1.471(12) . ?
C14A H14A 1.0000 . ?
C14A C15A 1.511(5) . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C14B H14B 1.0000 . ?
C14B C15B 1.508(19) . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Pd1 Cl1 180.00(2) 3 . ?
N1 Pd1 Cl1 90.44(5) 3 3 ?
N1 Pd1 Cl1 90.44(5) . . ?
N1 Pd1 Cl1 89.56(5) 3 . ?
N1 Pd1 Cl1 89.56(5) . 3 ?
N1 Pd1 N1 180.0 . 3 ?
C1 N1 Pd1 122.72(15) . . ?
C1 N1 C5 116.86(19) . . ?
C5 N1 Pd1 120.37(15) . . ?
C6 N2 C3 122.20(19) . . ?
C6 N3 C7 109.10(18) . . ?
C6 N3 C11 122.31(18) . . ?
C7 N3 C11 127.39(18) . . ?
C6 N4 C8 109.32(19) . . ?
C6 N4 C14A 118.2(2) . . ?
C6 N4 C14B 142.3(7) . . ?
C8 N4 C14A 132.0(2) . . ?
C14B N4 C8 106.2(7) . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.1(2) . . ?
C2 C1 H1 118.4 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.1(2) . . ?
C3 C2 H2 119.5 . . ?
N2 C3 C2 127.0(2) . . ?
N2 C3 C4 118.4(2) . . ?
C2 C3 C4 114.4(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
N1 C5 C4 123.5(2) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
N2 C6 N3 129.8(2) . . ?
N2 C6 N4 122.7(2) . . ?
N4 C6 N3 107.14(19) . . ?
N3 C7 C9 124.4(2) . . ?
C8 C7 N3 107.0(2) . . ?
C8 C7 C9 128.4(2) . . ?
N4 C8 C10 124.0(2) . . ?
C7 C8 N4 107.41(19) . . ?
C7 C8 C10 128.5(2) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 H11 106.8 . . ?
N3 C11 C12 112.18(18) . . ?
N3 C11 C13 110.89(17) . . ?
C12 C11 H11 106.8 . . ?
C12 C11 C13 112.87(19) . . ?
C13 C11 H11 106.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H16D C16 H16E 109.5 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 109.5 . . ?
C14A C16 H16A 109.5 . . ?
C14A C16 H16B 109.5 . . ?
C14A C16 H16C 109.5 . . ?
C14B C16 H16D 109.5 . . ?
C14B C16 H16E 109.5 . . ?
C14B C16 H16F 109.5 . . ?
N4 C14A C16 107.2(2) . . ?
N4 C14A H14A 106.9 . . ?
C16 C14A H14A 106.9 . . ?
C15A C14A N4 112.5(3) . . ?
C15A C14A C16 116.0(3) . . ?
C15A C14A H14A 106.9 . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
C14A C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
N4 C14B C16 117.1(8) . . ?
N4 C14B H14B 108.9 . . ?
N4 C14B C15B 103.6(10) . . ?
C16 C14B H14B 108.9 . . ?
C16 C14B C15B 109.1(11) . . ?
C15B C14B H14B 108.9 . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 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 C1 C2 -175.77(15) . . . . ?
Pd1 N1 C5 C4 176.41(17) . . . . ?
N1 C1 C2 C3 -0.6(3) . . . . ?
N2 C3 C4 C5 178.7(2) . . . . ?
N3 C7 C8 N4 0.5(2) . . . . ?
N3 C7 C8 C10 -178.1(2) . . . . ?
C1 N1 C5 C4 -1.2(3) . . . . ?
C1 C2 C3 N2 -177.9(2) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C3 N2 C6 N3 -58.2(3) . . . . ?
C3 N2 C6 N4 129.6(2) . . . . ?
C3 C4 C5 N1 -0.6(4) . . . . ?
C5 N1 C1 C2 1.8(3) . . . . ?
C6 N2 C3 C2 -10.2(3) . . . . ?
C6 N2 C3 C4 173.2(2) . . . . ?
C6 N3 C7 C8 0.0(2) . . . . ?
C6 N3 C7 C9 -175.1(2) . . . . ?
C6 N3 C11 C12 129.3(2) . . . . ?
C6 N3 C11 C13 -103.5(2) . . . . ?
C6 N4 C8 C7 -0.9(2) . . . . ?
C6 N4 C8 C10 177.9(2) . . . . ?
C6 N4 C14A C16 -99.3(3) . . . . ?
C6 N4 C14A C15A 132.1(3) . . . . ?
C6 N4 C14B C16 -51.5(16) . . . . ?
C6 N4 C14B C15B 68.6(12) . . . . ?
C7 N3 C6 N2 -173.7(2) . . . . ?
C7 N3 C6 N4 -0.6(2) . . . . ?
C7 N3 C11 C12 -64.6(3) . . . . ?
C7 N3 C11 C13 62.6(3) . . . . ?
C8 N4 C6 N2 174.6(2) . . . . ?
C8 N4 C6 N3 0.9(2) . . . . ?
C8 N4 C14A C16 71.3(3) . . . . ?
C8 N4 C14A C15A -57.4(4) . . . . ?
C8 N4 C14B C16 108.3(10) . . . . ?
C8 N4 C14B C15B -131.6(9) . . . . ?
C9 C7 C8 N4 175.4(2) . . . . ?
C9 C7 C8 C10 -3.3(4) . . . . ?
C11 N3 C6 N2 -5.3(3) . . . . ?
C11 N3 C6 N4 167.80(18) . . . . ?
C11 N3 C7 C8 -167.6(2) . . . . ?
C11 N3 C7 C9 17.3(3) . . . . ?
C14A N4 C6 N2 -12.8(3) . . . . ?
C14A N4 C6 N3 173.5(2) . . . . ?
C14A N4 C8 C7 -172.1(2) . . . . ?
C14A N4 C8 C10 6.7(4) . . . . ?
C14B N4 C6 N2 -26.0(9) . . . . ?
C14B N4 C6 N3 160.3(9) . . . . ?
C14B N4 C8 C7 -168.0(5) . . . . ?
C14B N4 C8 C10 10.8(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_4
_database_code_depnum_ccdc_archive 'CCDC 2354127'
loop_
_audit_author_name
_audit_author_address
'Michael Seidl'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_audit_creation_date             2024-05-08
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H24 N4 O2 S, C2 H4 O0.5'
_chemical_formula_sum            'C18 H28 N4 O2.50 S'
_chemical_formula_weight         372.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.7329(3)
_cell_length_b                   10.41810(10)
_cell_length_c                   17.8347(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.7146(6)
_cell_angle_gamma                90
_cell_volume                     3833.10(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.593
_cell_measurement_theta_min      2.875
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
? was used for absorption correction.
wR2(int) was 0.1033 before and 0.0387 after correction.
The Ratio of minimum to maximum transmission is 0.8888.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            32208
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.614
_diffrn_reflns_theta_min         3.550
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4791
_reflns_number_total             5386
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_collection       'Bruker Apex III'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.983
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         5386
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0595P)²+7.7599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1412
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(C16A)=
 Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C16)=Sof(H16A)=
 Sof(H16B)=Sof(H16C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C14A(H14A)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
3.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C15(H15A,H15B,H15C), C15A(H15D,H15E,H15F), C16(H16A,H16B,H16C),
 C16A(H16D,H16E,H16F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.45510(2) 0.70800(4) 0.47947(2) 0.02996(12) Uani 1 1 d . . . . .
O1 O 0.51515(6) 0.66098(18) 0.45841(9) 0.0481(4) Uani 1 1 d . . . A 2
O2 O 0.43905(11) 0.83642(17) 0.45893(15) 0.0961(10) Uani 1 1 d . . . B 1
N1 N 0.39226(6) 0.62075(13) 0.40529(7) 0.0208(2) Uani 1 1 d . . . . .
N2 N 0.24954(8) 0.43484(14) 0.26640(8) 0.0300(3) Uani 1 1 d . . . . .
N3 N 0.22441(6) 0.51372(12) 0.14003(7) 0.0215(3) Uani 1 1 d . . . . .
N4 N 0.14855(7) 0.53003(15) 0.21517(9) 0.0317(3) Uani 1 1 d . . . . .
C1 C 0.38477(8) 0.49223(15) 0.40823(8) 0.0235(3) Uani 1 1 d . . . . .
H1 H 0.412756 0.443784 0.442903 0.028 Uiso 1 1 calc R U . . .
C2 C 0.33802(8) 0.43007(15) 0.36265(9) 0.0255(3) Uani 1 1 d . . . . .
H2 H 0.333817 0.339560 0.366470 0.031 Uiso 1 1 calc R U . . .
C3 C 0.29539(7) 0.49907(14) 0.30938(8) 0.0204(3) Uani 1 1 d . . . . .
C4 C 0.30485(7) 0.63471(14) 0.30832(8) 0.0195(3) Uani 1 1 d . . . . .
H4 H 0.278236 0.686739 0.274156 0.023 Uiso 1 1 calc R U . . .
C5 C 0.35249(7) 0.68971(14) 0.35679(8) 0.0209(3) Uani 1 1 d . . . . .
H5 H 0.357560 0.780309 0.356009 0.025 Uiso 1 1 calc R U . . .
C6 C 0.21110(8) 0.49458(14) 0.21188(8) 0.0231(3) Uani 1 1 d . . . . .
C7 C 0.16891(8) 0.56134(15) 0.09776(9) 0.0269(3) Uani 1 1 d . . . . .
C8 C 0.12228(8) 0.57122(17) 0.14437(12) 0.0333(4) Uani 1 1 d . . . . .
C9 C 0.16344(11) 0.5868(2) 0.01514(11) 0.0433(5) Uani 1 1 d . . . . .
H9A H 0.202261 0.632106 0.002291 0.065 Uiso 1 1 calc R U . . .
H9B H 0.125069 0.639703 0.001059 0.065 Uiso 1 1 calc R U . . .
H9C H 0.159380 0.505155 -0.012266 0.065 Uiso 1 1 calc R U . . .
C10 C 0.05351(10) 0.6130(2) 0.12633(17) 0.0544(6) Uani 1 1 d . . . . .
H10A H 0.024469 0.540999 0.134101 0.082 Uiso 1 1 calc R U . . .
H10B H 0.046846 0.640979 0.073676 0.082 Uiso 1 1 calc R U . . .
H10C H 0.044128 0.684274 0.159398 0.082 Uiso 1 1 calc R U . . .
C11 C 0.28833(8) 0.48404(17) 0.11493(9) 0.0276(3) Uani 1 1 d . . . . .
H11 H 0.315124 0.446413 0.159266 0.033 Uiso 1 1 calc R U . . .
C12 C 0.28339(9) 0.38220(18) 0.05363(11) 0.0338(4) Uani 1 1 d . . . . .
H12A H 0.256904 0.310574 0.068735 0.051 Uiso 1 1 calc R U . . .
H12B H 0.326859 0.351004 0.046074 0.051 Uiso 1 1 calc R U . . .
H12C H 0.263201 0.419361 0.006532 0.051 Uiso 1 1 calc R U . . .
C13 C 0.32297(11) 0.6049(2) 0.09315(12) 0.0440(5) Uani 1 1 d . . . . .
H13A H 0.300870 0.639964 0.046468 0.066 Uiso 1 1 calc R U . . .
H13B H 0.367923 0.584120 0.085403 0.066 Uiso 1 1 calc R U . . .
H13C H 0.322445 0.668596 0.133518 0.066 Uiso 1 1 calc R U . . .
C14 C 0.10846(16) 0.5337(3) 0.27768(19) 0.0242(7) Uani 0.692(10) 1 d . . P C 1
H14 H 0.065367 0.570816 0.258909 0.029 Uiso 0.692(10) 1 calc R U P C 1
C14A C 0.1305(4) 0.4982(7) 0.3012(4) 0.0259(16) Uani 0.308(10) 1 d . . P C 2
H14A H 0.169416 0.462354 0.331836 0.031 Uiso 0.308(10) 1 calc R U P C 2
C15 C 0.0980(3) 0.3981(6) 0.3034(4) 0.0356(10) Uani 0.692(10) 1 d . . P C 1
H15A H 0.074952 0.349126 0.262085 0.053 Uiso 0.692(10) 1 calc R U P C 1
H15B H 0.072169 0.399249 0.346522 0.053 Uiso 0.692(10) 1 calc R U P C 1
H15C H 0.140004 0.357694 0.318243 0.053 Uiso 0.692(10) 1 calc R U P C 1
C15A C 0.0752(5) 0.3997(14) 0.2963(8) 0.032(2) Uani 0.308(10) 1 d . . P C 2
H15D H 0.037412 0.434807 0.265626 0.049 Uiso 0.308(10) 1 calc R U P C 2
H15E H 0.063457 0.380997 0.347101 0.049 Uiso 0.308(10) 1 calc R U P C 2
H15F H 0.089241 0.320543 0.273176 0.049 Uiso 0.308(10) 1 calc R U P C 2
C16 C 0.1395(2) 0.6204(4) 0.3398(2) 0.0310(8) Uani 0.692(10) 1 d . . P C 1
H16A H 0.180241 0.582160 0.361654 0.046 Uiso 0.692(10) 1 calc R U P C 1
H16B H 0.109946 0.630233 0.379042 0.046 Uiso 0.692(10) 1 calc R U P C 1
H16C H 0.148166 0.704799 0.318659 0.046 Uiso 0.692(10) 1 calc R U P C 1
C16A C 0.1135(5) 0.6287(9) 0.3321(5) 0.0330(18) Uani 0.308(10) 1 d . . P C 2
H16D H 0.150538 0.686831 0.330941 0.050 Uiso 0.308(10) 1 calc R U P C 2
H16E H 0.102914 0.619049 0.384159 0.050 Uiso 0.308(10) 1 calc R U P C 2
H16F H 0.076020 0.664293 0.301137 0.050 Uiso 0.308(10) 1 calc R U P C 2
O3 O 0.500000 0.34114(19) 0.250000 0.0442(5) Uani 1 2 d S T P . .
C17 C 0.53069(10) 0.4206(2) 0.30871(12) 0.0390(4) Uani 1 1 d . . . . .
H17A H 0.575790 0.391767 0.322681 0.047 Uiso 1 1 calc R U . . .
H17B H 0.506751 0.416406 0.353984 0.047 Uiso 1 1 calc R U . . .
C18 C 0.53002(9) 0.55552(18) 0.27818(10) 0.0334(4) Uani 1 1 d . . . . .
H18A H 0.569577 0.573682 0.253175 0.040 Uiso 1 1 calc R U . . .
H18B H 0.526255 0.619420 0.318598 0.040 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4229(15) . ?
S1 O2 1.4180(19) . ?
S1 N1 1.9826(13) . ?
N1 C1 1.350(2) . ?
N1 C5 1.3424(19) . ?
N2 C3 1.3394(19) . ?
N2 C6 1.347(2) . ?
N3 C6 1.3522(19) . ?
N3 C7 1.4020(19) . ?
N3 C11 1.473(2) . ?
N4 C6 1.355(2) . ?
N4 C8 1.392(3) . ?
N4 C14 1.456(3) . ?
N4 C14A 1.648(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.365(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.426(2) . ?
C3 C4 1.427(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.372(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.340(3) . ?
C7 C9 1.490(3) . ?
C8 C10 1.495(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.520(3) . ?
C11 C13 1.519(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 1.0000 . ?
C14 C15 1.508(7) . ?
C14 C16 1.521(5) . ?
C14A H14A 1.0000 . ?
C14A C15A 1.536(15) . ?
C14A C16A 1.522(12) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 0.9800 . ?
O3 C17 1.433(2) 2_655 ?
O3 C17 1.433(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.507(3) . ?
C18 C18 1.520(4) 2_655 ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 101.54(7) . . ?
O2 S1 N1 97.96(8) . . ?
C1 N1 S1 119.97(10) . . ?
C5 N1 S1 120.35(11) . . ?
C5 N1 C1 119.36(13) . . ?
C3 N2 C6 121.17(14) . . ?
C6 N3 C7 109.13(13) . . ?
C6 N3 C11 122.12(13) . . ?
C7 N3 C11 128.74(13) . . ?
C6 N4 C8 109.53(14) . . ?
C6 N4 C14 131.5(2) . . ?
C6 N4 C14A 107.0(3) . . ?
C8 N4 C14 119.0(2) . . ?
C8 N4 C14A 143.3(3) . . ?
N1 C1 H1 119.2 . . ?
N1 C1 C2 121.69(14) . . ?
C2 C1 H1 119.2 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 120.92(14) . . ?
C3 C2 H2 119.5 . . ?
N2 C3 C2 119.14(14) . . ?
N2 C3 C4 125.29(14) . . ?
C2 C3 C4 115.54(13) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.77(13) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 122.69(14) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
N2 C6 N3 126.19(15) . . ?
N2 C6 N4 126.49(15) . . ?
N3 C6 N4 106.70(14) . . ?
N3 C7 C9 124.90(16) . . ?
C8 C7 N3 107.32(15) . . ?
C8 C7 C9 127.66(17) . . ?
N4 C8 C10 124.3(2) . . ?
C7 C8 N4 107.32(15) . . ?
C7 C8 C10 128.3(2) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 H11 106.7 . . ?
N3 C11 C12 111.52(13) . . ?
N3 C11 C13 111.48(16) . . ?
C12 C11 H11 106.7 . . ?
C13 C11 H11 106.7 . . ?
C13 C11 C12 113.23(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14 108.2 . . ?
N4 C14 C15 108.6(3) . . ?
N4 C14 C16 109.9(2) . . ?
C15 C14 H14 108.2 . . ?
C15 C14 C16 113.5(5) . . ?
C16 C14 H14 108.2 . . ?
N4 C14A H14A 109.8 . . ?
C15A C14A N4 108.6(7) . . ?
C15A C14A H14A 109.8 . . ?
C16A C14A N4 103.9(6) . . ?
C16A C14A H14A 109.8 . . ?
C16A C14A C15A 114.7(9) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14A C15A H15D 109.5 . . ?
C14A C15A H15E 109.5 . . ?
C14A C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14A C16A H16D 109.5 . . ?
C14A C16A H16E 109.5 . . ?
C14A C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C17 O3 C17 109.4(2) 2_655 . ?
O3 C17 H17A 110.4 . . ?
O3 C17 H17B 110.4 . . ?
O3 C17 C18 106.70(16) . . ?
H17A C17 H17B 108.6 . . ?
C18 C17 H17A 110.4 . . ?
C18 C17 H17B 110.4 . . ?
C17 C18 C18 102.50(11) . 2_655 ?
C17 C18 H18A 111.3 . . ?
C17 C18 H18B 111.3 . . ?
C18 C18 H18A 111.3 2_655 . ?
C18 C18 H18B 111.3 2_655 . ?
H18A C18 H18B 109.2 . . ?

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
S1 N1 C1 C2 174.00(12) . . . . ?
S1 N1 C5 C4 -174.88(11) . . . . ?
N1 C1 C2 C3 0.5(2) . . . . ?
N2 C3 C4 C5 178.11(15) . . . . ?
N3 C7 C8 N4 0.00(18) . . . . ?
N3 C7 C8 C10 -177.78(18) . . . . ?
C1 N1 C5 C4 -1.4(2) . . . . ?
C1 C2 C3 N2 -179.07(15) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 N2 C6 N3 86.9(2) . . . . ?
C3 N2 C6 N4 -103.4(2) . . . . ?
C3 C4 C5 N1 1.2(2) . . . . ?
C5 N1 C1 C2 0.5(2) . . . . ?
C6 N2 C3 C2 -175.45(15) . . . . ?
C6 N2 C3 C4 6.4(2) . . . . ?
C6 N3 C7 C8 0.21(18) . . . . ?
C6 N3 C7 C9 -176.10(16) . . . . ?
C6 N3 C11 C12 118.70(16) . . . . ?
C6 N3 C11 C13 -113.65(17) . . . . ?
C6 N4 C8 C7 -0.21(19) . . . . ?
C6 N4 C8 C10 177.68(17) . . . . ?
C6 N4 C14 C15 -66.3(4) . . . . ?
C6 N4 C14 C16 58.4(4) . . . . ?
C6 N4 C14A C15A -118.7(7) . . . . ?
C6 N4 C14A C16A 118.8(7) . . . . ?
C7 N3 C6 N2 171.06(14) . . . . ?
C7 N3 C6 N4 -0.33(17) . . . . ?
C7 N3 C11 C12 -60.0(2) . . . . ?
C7 N3 C11 C13 67.6(2) . . . . ?
C8 N4 C6 N2 -171.02(15) . . . . ?
C8 N4 C6 N3 0.33(18) . . . . ?
C8 N4 C14 C15 115.3(4) . . . . ?
C8 N4 C14 C16 -120.0(3) . . . . ?
C8 N4 C14A C15A 55.1(9) . . . . ?
C8 N4 C14A C16A -67.4(7) . . . . ?
C9 C7 C8 N4 176.18(17) . . . . ?
C9 C7 C8 C10 -1.6(3) . . . . ?
C11 N3 C6 N2 -7.9(2) . . . . ?
C11 N3 C6 N4 -179.29(14) . . . . ?
C11 N3 C7 C8 179.07(15) . . . . ?
C11 N3 C7 C9 2.8(3) . . . . ?
C14 N4 C6 N2 10.5(3) . . . . ?
C14 N4 C6 N3 -178.15(18) . . . . ?
C14 N4 C8 C7 178.50(17) . . . . ?
C14 N4 C8 C10 -3.6(3) . . . . ?
C14A N4 C6 N2 5.1(3) . . . . ?
C14A N4 C6 N3 176.4(2) . . . . ?
C14A N4 C8 C7 -173.9(4) . . . . ?
C14A N4 C8 C10 4.0(5) . . . . ?
O3 C17 C18 C18 28.7(2) . . . 2_655 ?
C17 O3 C17 C18 -11.28(9) 2_655 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_5
_database_code_depnum_ccdc_archive 'CCDC 2354128'
loop_
_audit_author_name
_audit_author_address
'Michael Seidl'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_audit_creation_date             2024-05-08
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H24 B2 Cl6 N4'
_chemical_formula_sum            'C16 H24 B2 Cl6 N4'
_chemical_formula_weight         506.71
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.52560(10)
_cell_length_b                   13.7012(2)
_cell_length_c                   12.0051(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.2128(8)
_cell_angle_gamma                90
_cell_volume                     1182.40(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6377
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.729
_cell_measurement_theta_min      2.974
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
? was used for absorption correction.
wR2(int) was 0.0889 before and 0.0360 after correction.
The Ratio of minimum to maximum transmission is 0.9095.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15766
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.746
_diffrn_reflns_theta_min         3.464
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2833
_reflns_number_total             3191
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_collection       'Bruker Apex III'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.7665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0951
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.76653(7) 0.36034(3) 1.44405(4) 0.02630(12) Uani 1 1 d . . . . .
Cl2 Cl 0.40548(8) 0.250000 1.34673(5) 0.02561(15) Uani 1 2 d S T P . .
Cl3 Cl 1.13725(5) 0.36191(3) 0.97775(4) 0.02240(11) Uani 1 1 d . . . . .
Cl4 Cl 0.99405(8) 0.250000 0.75215(5) 0.02460(14) Uani 1 2 d S T P . .
N1 N 0.6933(3) 0.250000 1.24178(16) 0.0161(4) Uani 1 2 d S T P . .
N2 N 0.8128(2) 0.250000 0.92152(16) 0.0130(3) Uani 1 2 d S T P . .
N3 N 0.57408(17) 0.32974(9) 0.76684(11) 0.0129(2) Uani 1 1 d . . . . .
C1 C 0.5568(3) 0.250000 1.13933(19) 0.0146(4) Uani 1 2 d S T P . .
H1 H 0.431105 0.250000 1.140505 0.017 Uiso 1 2 calc R U P . .
C2 C 0.5919(3) 0.250000 1.03360(18) 0.0131(4) Uani 1 2 d S T P . .
H2 H 0.490975 0.250000 0.963779 0.016 Uiso 1 2 calc R U P . .
C3 C 0.7749(3) 0.250000 1.02729(18) 0.0134(4) Uani 1 2 d S T P . .
C4 C 0.9166(3) 0.250000 1.1352(2) 0.0195(5) Uani 1 2 d S T P . .
H4 H 1.043515 0.250000 1.136718 0.023 Uiso 1 2 calc R U P . .
C5 C 0.8713(3) 0.250000 1.2374(2) 0.0202(5) Uani 1 2 d S T P . .
H5 H 0.969126 0.250000 1.308720 0.024 Uiso 1 2 calc R U P . .
C6 C 0.6596(3) 0.250000 0.82194(18) 0.0121(4) Uani 1 2 d S T P . .
C7 C 0.4275(2) 0.29970(11) 0.67162(13) 0.0145(3) Uani 1 1 d . . . . .
C8 C 0.2959(2) 0.36724(12) 0.59026(15) 0.0212(3) Uani 1 1 d . . . . .
H8A H 0.215335 0.329906 0.525098 0.032 Uiso 1 1 calc R U . . .
H8B H 0.366246 0.415543 0.560315 0.032 Uiso 1 1 calc R U . . .
H8C H 0.219437 0.400708 0.631852 0.032 Uiso 1 1 calc R U . . .
C9 C 0.6345(2) 0.43050(11) 0.80703(14) 0.0167(3) Uani 1 1 d . . . . .
H9 H 0.737630 0.424054 0.881596 0.020 Uiso 1 1 calc R U . . .
C10 C 0.7148(3) 0.48306(13) 0.72120(17) 0.0277(4) Uani 1 1 d . . . . .
H10A H 0.807613 0.441302 0.702335 0.042 Uiso 1 1 calc R U . . .
H10B H 0.773706 0.544016 0.756177 0.042 Uiso 1 1 calc R U . . .
H10C H 0.614698 0.497715 0.649789 0.042 Uiso 1 1 calc R U . . .
C11 C 0.4783(2) 0.48673(12) 0.83536(15) 0.0216(3) Uani 1 1 d . . . . .
H11A H 0.385653 0.506491 0.762695 0.032 Uiso 1 1 calc R U . . .
H11B H 0.529674 0.544871 0.881142 0.032 Uiso 1 1 calc R U . . .
H11C H 0.419244 0.444941 0.880421 0.032 Uiso 1 1 calc R U . . .
B1 B 0.6579(4) 0.250000 1.3653(2) 0.0188(5) Uani 1 2 d S T P . .
B2 B 1.0101(4) 0.250000 0.9080(2) 0.0178(5) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 B1 1.8412(16) . ?
Cl2 B1 1.846(3) . ?
Cl3 B2 1.8691(16) . ?
Cl4 B2 1.839(3) . ?
N1 C1 1.349(3) . ?
N1 C5 1.356(3) . ?
N1 B1 1.583(3) . ?
N2 C3 1.381(3) . ?
N2 C6 1.394(3) . ?
N2 B2 1.541(3) . ?
N3 C6 1.3390(17) . ?
N3 C7 1.3952(19) . ?
N3 C9 1.489(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.371(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(3) . ?
C3 C4 1.413(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.367(3) . ?
C5 H5 0.9500 . ?
C7 C7 1.362(3) 4_565 ?
C7 C8 1.490(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9 1.0000 . ?
C9 C10 1.521(2) . ?
C9 C11 1.526(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 117.32(19) . . ?
C1 N1 B1 124.08(19) . . ?
C5 N1 B1 118.59(19) . . ?
C3 N2 C6 116.43(17) . . ?
C3 N2 B2 124.37(18) . . ?
C6 N2 B2 119.20(18) . . ?
C6 N3 C7 108.17(13) . . ?
C6 N3 C9 122.72(13) . . ?
C7 N3 C9 129.11(13) . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.7(2) . . ?
C2 C1 H1 118.6 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
N2 C3 C2 121.54(19) . . ?
N2 C3 C4 122.51(19) . . ?
C2 C3 C4 115.94(19) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 123.1(2) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
N3 C6 N2 125.33(9) . . ?
N3 C6 N2 125.33(9) 4_565 . ?
N3 C6 N3 109.35(18) . 4_565 ?
N3 C7 C8 124.41(14) . . ?
C7 C7 N3 107.15(8) 4_565 . ?
C7 C7 C8 128.41(9) 4_565 . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9 106.9 . . ?
N3 C9 C10 111.35(13) . . ?
N3 C9 C11 111.02(13) . . ?
C10 C9 H9 106.9 . . ?
C10 C9 C11 113.49(14) . . ?
C11 C9 H9 106.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Cl1 B1 Cl1 110.39(14) 4_565 . ?
Cl1 B1 Cl2 110.30(10) . . ?
Cl1 B1 Cl2 110.30(10) 4_565 . ?
N1 B1 Cl1 107.98(11) . . ?
N1 B1 Cl1 107.98(11) . 4_565 ?
N1 B1 Cl2 109.83(16) . . ?
Cl3 B2 Cl3 110.24(14) 4_565 . ?
Cl4 B2 Cl3 109.08(9) . . ?
Cl4 B2 Cl3 109.08(9) . 4_565 ?
N2 B2 Cl3 109.52(10) . . ?
N2 B2 Cl3 109.52(10) . 4_565 ?
N2 B2 Cl4 109.39(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
N1 C1 C2 C3 0.000(2) . . . . ?
N2 C3 C4 C5 180.000(2) . . . . ?
C1 N1 C5 C4 0.000(2) . . . . ?
C1 N1 B1 Cl1 -120.31(11) . . . . ?
C1 N1 B1 Cl1 120.31(11) . . . 4_565 ?
C1 N1 B1 Cl2 0.000(2) . . . . ?
C1 C2 C3 N2 180.000(1) . . . . ?
C1 C2 C3 C4 0.000(2) . . . . ?
C2 C3 C4 C5 0.000(2) . . . . ?
C3 N2 C6 N3 89.76(18) . . . . ?
C3 N2 C6 N3 -89.76(18) . . . 4_565 ?
C3 N2 B2 Cl3 -60.50(11) . . . . ?
C3 N2 B2 Cl3 60.50(11) . . . 4_565 ?
C3 N2 B2 Cl4 180.000(1) . . . . ?
C3 C4 C5 N1 0.000(2) . . . . ?
C5 N1 C1 C2 0.000(2) . . . . ?
C5 N1 B1 Cl1 59.69(11) . . . . ?
C5 N1 B1 Cl1 -59.69(11) . . . 4_565 ?
C5 N1 B1 Cl2 180.000(1) . . . . ?
C6 N2 C3 C2 0.000(2) . . . . ?
C6 N2 C3 C4 180.000(1) . . . . ?
C6 N2 B2 Cl3 -119.50(11) . . . 4_565 ?
C6 N2 B2 Cl3 119.50(11) . . . . ?
C6 N2 B2 Cl4 0.000(1) . . . . ?
C6 N3 C7 C7 0.19(13) . . . 4_565 ?
C6 N3 C7 C8 178.35(15) . . . . ?
C6 N3 C9 C10 112.12(18) . . . . ?
C6 N3 C9 C11 -120.39(17) . . . . ?
C7 N3 C6 N2 -179.90(17) . . . . ?
C7 N3 C6 N3 -0.3(2) . . . 4_565 ?
C7 N3 C9 C10 -68.1(2) . . . . ?
C7 N3 C9 C11 59.35(19) . . . . ?
C9 N3 C6 N2 -0.1(3) . . . . ?
C9 N3 C6 N3 179.47(10) . . . 4_565 ?
C9 N3 C7 C7 -179.57(12) . . . 4_565 ?
C9 N3 C7 C8 -1.4(2) . . . . ?
B1 N1 C1 C2 180.000(2) . . . . ?
B1 N1 C5 C4 180.000(2) . . . . ?
B2 N2 C3 C2 180.000(1) . . . . ?
B2 N2 C3 C4 0.000(2) . . . . ?
B2 N2 C6 N3 -90.24(18) . . . . ?
B2 N2 C6 N3 90.24(18) . . . 4_565 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_12
_database_code_depnum_ccdc_archive 'CCDC 2354132'
loop_
_audit_author_name
_audit_author_address
'Michael Seidl'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_audit_creation_date             2024-05-08
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I, C17 H29 N4'
_chemical_formula_sum            'C17 H29 I N4'
_chemical_formula_weight         416.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.5821(3)
_cell_length_b                   12.4611(4)
_cell_length_c                   18.6160(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.4610(10)
_cell_angle_gamma                90
_cell_volume                     1978.20(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9326
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      26.774
_cell_measurement_theta_min      2.389
_shelx_estimated_absorpt_T_max   0.748
_shelx_estimated_absorpt_T_min   0.601
_exptl_absorpt_coefficient_mu    1.622
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1088 before and 0.0448 after correction.
The Ratio of minimum to maximum transmission is 0.8051.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            41828
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.805
_diffrn_reflns_theta_min         2.202
_diffrn_ambient_temperature      173.00
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C14'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3988
_reflns_number_total             4168
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker Apex 4 v2021.4-0'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0241
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+0.8375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0672
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: I1(0.666667) I1A(0.333333) C9(0.8) H9A(0.8) H9B(0.8) H9C(0.8)
 C10(0.8) H10A(0.8) H10B(0.8) H10C(0.8) C11(0.8) H11A(0.8) H11B(0.8) H11C(0.8)
 C9A(0.2) H9AA(0.2) H9AB(0.2) H9AC(0.2) C10A(0.2) H10D(0.2) H10E(0.2) H10F(0.2)
 C11A(0.2) H11D(0.2) H11E(0.2) H11F(0.2)
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C17(H17A,H17B,H17C),
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C9A(H9AA,H9AB,H9AC),
  C10A(H10D,H10E,H10F), C11A(H11D,H11E,H11F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.85431(16) 0.48637(10) 0.81387(7) 0.05134(19) Uani 0.6667 1 d . . P . .
I1A I 0.8343(3) 0.5039(2) 0.82247(15) 0.0519(4) Uani 0.3333 1 d . . P . .
N1 N 0.55829(13) 0.64949(9) 0.45524(6) 0.0277(2) Uani 1 1 d . . . . .
N2 N 0.54899(14) 0.71864(10) 0.33713(6) 0.0302(2) Uani 1 1 d . . . . .
N3 N 0.41844(17) 0.80739(12) 0.41479(7) 0.0411(3) Uani 1 1 d . . . . .
N4 N 0.90973(14) 0.68042(11) 0.62430(7) 0.0335(3) Uani 1 1 d . . . . .
C1 C 0.51375(15) 0.72406(11) 0.40515(7) 0.0257(3) Uani 1 1 d . . . . .
C2 C 0.4772(2) 0.80733(16) 0.29431(9) 0.0484(4) Uani 1 1 d . . . . .
H2A H 0.410596 0.780644 0.251136 0.058 Uiso 1 1 calc R U . . .
H2B H 0.558009 0.856033 0.278619 0.058 Uiso 1 1 calc R U . . .
C3 C 0.3802(3) 0.86319(19) 0.34543(10) 0.0606(6) Uani 1 1 d . . . . .
H3A H 0.408197 0.940158 0.349939 0.073 Uiso 1 1 calc R U . . .
H3B H 0.267001 0.856904 0.328537 0.073 Uiso 1 1 calc R U . . .
C4 C 0.66155(17) 0.64242(12) 0.30850(8) 0.0328(3) Uani 1 1 d . . . . .
C5 C 0.6092(2) 0.52747(14) 0.31958(11) 0.0461(4) Uani 1 1 d . . . . .
H5A H 0.614305 0.512335 0.371448 0.069 Uiso 1 1 calc R U . . .
H5B H 0.678335 0.477933 0.297314 0.069 Uiso 1 1 calc R U . . .
H5C H 0.501182 0.518135 0.297098 0.069 Uiso 1 1 calc R U . . .
C6 C 0.82679(19) 0.66289(17) 0.34520(11) 0.0497(4) Uani 1 1 d . . . . .
H6A H 0.850581 0.739677 0.343158 0.075 Uiso 1 1 calc R U . . .
H6B H 0.902396 0.622320 0.320239 0.075 Uiso 1 1 calc R U . . .
H6C H 0.833588 0.639836 0.395784 0.075 Uiso 1 1 calc R U . . .
C7 C 0.6587(3) 0.66141(18) 0.22714(10) 0.0551(5) Uani 1 1 d . . . . .
H7A H 0.552969 0.647451 0.203219 0.083 Uiso 1 1 calc R U . . .
H7B H 0.733418 0.612967 0.207621 0.083 Uiso 1 1 calc R U . . .
H7C H 0.687753 0.735957 0.218475 0.083 Uiso 1 1 calc R U . . .
C8 C 0.31227(19) 0.81940(17) 0.47237(10) 0.0455(4) Uani 1 1 d . . . . .
C12 C 0.67118(15) 0.66418(11) 0.50879(7) 0.0256(3) Uani 1 1 d . . . . .
C13 C 0.76854(16) 0.75689(11) 0.51971(7) 0.0267(3) Uani 1 1 d . . . . .
H13 H 0.753621 0.815348 0.486903 0.032 Uiso 1 1 calc R U . . .
C14 C 0.88262(16) 0.76244(12) 0.57667(8) 0.0299(3) Uani 1 1 d . . . . .
H14 H 0.944881 0.825465 0.583218 0.036 Uiso 1 1 calc R U . . .
C15 C 0.81927(19) 0.59090(14) 0.61601(9) 0.0384(3) Uani 1 1 d . . . . .
H15 H 0.838343 0.533842 0.649695 0.046 Uiso 1 1 calc R U . . .
C16 C 0.70271(18) 0.58067(13) 0.56111(8) 0.0353(3) Uani 1 1 d . . . . .
H16 H 0.641020 0.517191 0.557268 0.042 Uiso 1 1 calc R U . . .
C17 C 1.0402(2) 0.68674(18) 0.68270(10) 0.0505(4) Uani 1 1 d . . . . .
H17A H 1.136050 0.659210 0.665236 0.076 Uiso 1 1 calc R U . . .
H17B H 1.015193 0.643580 0.723895 0.076 Uiso 1 1 calc R U . . .
H17C H 1.056148 0.761628 0.697839 0.076 Uiso 1 1 calc R U . . .
C9 C 0.1835(4) 0.7338(4) 0.4509(2) 0.1138(18) Uani 0.8 1 d . . P A 1
H9A H 0.135381 0.747481 0.401508 0.171 Uiso 0.8 1 calc R U P A 1
H9B H 0.103030 0.737791 0.484260 0.171 Uiso 0.8 1 calc R U P A 1
H9C H 0.230837 0.662126 0.453510 0.171 Uiso 0.8 1 calc R U P A 1
C10 C 0.3889(3) 0.7980(2) 0.54694(12) 0.0498(6) Uani 0.8 1 d . . P A 1
H10A H 0.318375 0.819641 0.582218 0.075 Uiso 0.8 1 calc R U P A 1
H10B H 0.486713 0.838992 0.555229 0.075 Uiso 0.8 1 calc R U P A 1
H10C H 0.412024 0.721184 0.552344 0.075 Uiso 0.8 1 calc R U P A 1
C11 C 0.2477(5) 0.9329(4) 0.46840(19) 0.0839(13) Uani 0.8 1 d . . P A 1
H11A H 0.177314 0.942787 0.505813 0.126 Uiso 0.8 1 calc R U P A 1
H11B H 0.189671 0.945022 0.420688 0.126 Uiso 0.8 1 calc R U P A 1
H11C H 0.334578 0.984193 0.476127 0.126 Uiso 0.8 1 calc R U P A 1
C9A C 0.278(2) 0.7389(12) 0.5258(9) 0.099(6) Uani 0.2 1 d . . P A 2
H9AA H 0.211095 0.682730 0.501929 0.148 Uiso 0.2 1 calc R U P A 2
H9AB H 0.223766 0.773200 0.563323 0.148 Uiso 0.2 1 calc R U P A 2
H9AC H 0.376314 0.707036 0.547881 0.148 Uiso 0.2 1 calc R U P A 2
C10A C 0.4377(12) 0.9050(11) 0.5248(6) 0.067(3) Uani 0.2 1 d . . P A 2
H10D H 0.376019 0.955579 0.550309 0.100 Uiso 0.2 1 calc R U P A 2
H10E H 0.502135 0.944731 0.493607 0.100 Uiso 0.2 1 calc R U P A 2
H10F H 0.505785 0.862912 0.560036 0.100 Uiso 0.2 1 calc R U P A 2
C11A C 0.1726(10) 0.8934(8) 0.4592(7) 0.040(2) Uani 0.2 1 d . . P A 2
H11D H 0.092076 0.859682 0.424964 0.060 Uiso 0.2 1 calc R U P A 2
H11E H 0.205392 0.961324 0.439006 0.060 Uiso 0.2 1 calc R U P A 2
H11F H 0.129839 0.907120 0.504913 0.060 Uiso 0.2 1 calc R U P A 2


_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
N1 C1 1.3412(17) . ?
N1 C12 1.3223(18) . ?
N2 C1 1.3362(18) . ?
N2 C2 1.4580(19) . ?
N2 C4 1.4951(19) . ?
N3 C1 1.3463(18) . ?
N3 C3 1.471(2) . ?
N3 C8 1.490(2) . ?
N4 C14 1.3558(19) . ?
N4 C15 1.358(2) . ?
N4 C17 1.4723(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.504(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.522(2) . ?
C4 C6 1.525(2) . ?
C4 C7 1.530(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.556(4) . ?
C8 C10 1.492(3) . ?
C8 C11 1.518(4) . ?
C8 C9A 1.465(12) . ?
C8 C10A 1.735(11) . ?
C8 C11A 1.510(10) . ?
C12 C13 1.4269(19) . ?
C12 C16 1.4302(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.362(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.353(2) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?

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
C12 N1 C1 123.75(12) . . ?
C1 N2 C2 110.67(12) . . ?
C1 N2 C4 126.45(12) . . ?
C2 N2 C4 122.47(12) . . ?
C1 N3 C3 109.06(13) . . ?
C1 N3 C8 127.08(14) . . ?
C3 N3 C8 119.33(14) . . ?
C14 N4 C15 119.41(12) . . ?
C14 N4 C17 120.19(14) . . ?
C15 N4 C17 120.35(14) . . ?
N1 C1 N3 124.86(13) . . ?
N2 C1 N1 123.14(13) . . ?
N2 C1 N3 111.77(12) . . ?
N2 C2 H2A 111.0 . . ?
N2 C2 H2B 111.0 . . ?
N2 C2 C3 103.58(13) . . ?
H2A C2 H2B 109.0 . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
N3 C3 C2 104.59(13) . . ?
N3 C3 H3A 110.8 . . ?
N3 C3 H3B 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
N2 C4 C5 109.70(13) . . ?
N2 C4 C6 109.86(12) . . ?
N2 C4 C7 108.39(13) . . ?
C5 C4 C6 111.76(15) . . ?
C5 C4 C7 107.90(15) . . ?
C6 C4 C7 109.16(15) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 102.76(17) . . ?
N3 C8 C10 114.21(14) . . ?
N3 C8 C11 107.9(2) . . ?
N3 C8 C10A 94.3(4) . . ?
N3 C8 C11A 118.8(5) . . ?
C10 C8 C9 110.0(3) . . ?
C10 C8 C11 109.4(2) . . ?
C11 C8 C9 112.4(3) . . ?
C9A C8 N3 127.2(5) . . ?
C9A C8 C10A 101.4(10) . . ?
C9A C8 C11A 108.2(7) . . ?
C11A C8 C10A 98.5(6) . . ?
N1 C12 C13 125.96(12) . . ?
N1 C12 C16 118.62(13) . . ?
C13 C12 C16 115.42(12) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.68(13) . . ?
C14 C13 H13 119.7 . . ?
N4 C14 C13 121.76(14) . . ?
N4 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
N4 C15 H15 119.1 . . ?
C16 C15 N4 121.86(14) . . ?
C16 C15 H15 119.1 . . ?
C12 C16 H16 119.6 . . ?
C15 C16 C12 120.86(14) . . ?
C15 C16 H16 119.6 . . ?
N4 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
N4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C9A H9AA 109.5 . . ?
C8 C9A H9AB 109.5 . . ?
C8 C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C8 C10A H10D 109.5 . . ?
C8 C10A H10E 109.5 . . ?
C8 C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C8 C11A H11D 109.5 . . ?
C8 C11A H11E 109.5 . . ?
C8 C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 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
N1 C12 C13 C14 -179.29(13) . . . . ?
N1 C12 C16 C15 178.55(15) . . . . ?
N2 C2 C3 N3 5.5(2) . . . . ?
N4 C15 C16 C12 0.7(3) . . . . ?
C1 N1 C12 C13 -3.9(2) . . . . ?
C1 N1 C12 C16 176.78(13) . . . . ?
C1 N2 C2 C3 -4.7(2) . . . . ?
C1 N2 C4 C5 59.63(19) . . . . ?
C1 N2 C4 C6 -63.59(19) . . . . ?
C1 N2 C4 C7 177.22(15) . . . . ?
C1 N3 C3 C2 -4.8(2) . . . . ?
C1 N3 C8 C9 -69.6(3) . . . . ?
C1 N3 C8 C10 49.5(3) . . . . ?
C1 N3 C8 C11 171.4(2) . . . . ?
C1 N3 C8 C9A -6.6(12) . . . . ?
C1 N3 C8 C10A 101.3(5) . . . . ?
C1 N3 C8 C11A -156.6(4) . . . . ?
C2 N2 C1 N1 176.65(14) . . . . ?
C2 N2 C1 N3 1.89(18) . . . . ?
C2 N2 C4 C5 -128.40(17) . . . . ?
C2 N2 C4 C6 108.38(18) . . . . ?
C2 N2 C4 C7 -10.8(2) . . . . ?
C3 N3 C1 N1 -172.70(16) . . . . ?
C3 N3 C1 N2 1.9(2) . . . . ?
C3 N3 C8 C9 83.8(3) . . . . ?
C3 N3 C8 C10 -157.0(2) . . . . ?
C3 N3 C8 C11 -35.1(3) . . . . ?
C3 N3 C8 C9A 146.8(12) . . . . ?
C3 N3 C8 C10A -105.3(5) . . . . ?
C3 N3 C8 C11A -3.2(5) . . . . ?
C4 N2 C1 N1 -10.6(2) . . . . ?
C4 N2 C1 N3 174.65(14) . . . . ?
C4 N2 C2 C3 -177.82(16) . . . . ?
C8 N3 C1 N1 -17.1(2) . . . . ?
C8 N3 C1 N2 157.57(15) . . . . ?
C8 N3 C3 C2 -162.57(17) . . . . ?
C12 N1 C1 N2 106.08(17) . . . . ?
C12 N1 C1 N3 -79.85(19) . . . . ?
C12 C13 C14 N4 1.0(2) . . . . ?
C13 C12 C16 C15 -0.9(2) . . . . ?
C14 N4 C15 C16 0.4(2) . . . . ?
C15 N4 C14 C13 -1.2(2) . . . . ?
C16 C12 C13 C14 0.08(19) . . . . ?
C17 N4 C14 C13 176.36(15) . . . . ?
C17 N4 C15 C16 -177.17(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_7
_database_code_depnum_ccdc_archive 'CCDC 2354130'
loop_
_audit_author_name
_audit_author_address
'Michael Seidl'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_audit_creation_date             2024-05-08
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C29 H42 Br2 N6 Pd, 2(C H Cl3)'
_chemical_formula_sum            'C31 H44 Br2 Cl6 N6 Pd'
_chemical_formula_weight         979.64
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4329(2)
_cell_length_b                   12.7505(3)
_cell_length_c                   30.4283(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.4543(10)
_cell_angle_gamma                90
_cell_volume                     4029.39(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9792
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      2.951
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.872
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
? was used for absorption correction.
wR2(int) was 0.1201 before and 0.0454 after correction.
The Ratio of minimum to maximum transmission is 0.7844.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1960
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            62658
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.060
_diffrn_reflns_theta_min         1.733
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9921
_reflns_number_total             11775
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_collection       'Bruker Apex III'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.978
_refine_diff_density_min         -1.236
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         11775
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+7.8721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0806
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C24(H24), C27(H27), C31(H31), C30(H30)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C20(H20), C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C25(H25A,H25B,H25C), C26(H26A,
 H26B,H26C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.74306(2) 0.68394(2) 0.32139(2) 0.01198(4) Uani 1 1 d . . . . .
Br1 Br 0.78410(2) 0.58214(2) 0.25698(2) 0.02007(6) Uani 1 1 d . . . . .
Br2 Br 0.69787(3) 0.79967(2) 0.38115(2) 0.02441(6) Uani 1 1 d . . . . .
N1 N 0.75886(18) 0.55251(15) 0.36247(6) 0.0148(4) Uani 1 1 d . . . . .
N2 N 0.7963(2) 0.28945(16) 0.44563(7) 0.0189(4) Uani 1 1 d . . . . .
N3 N 1.0225(2) 0.25319(17) 0.46728(7) 0.0192(4) Uani 1 1 d . . . . .
N4 N 0.9056(2) 0.12671(16) 0.43645(7) 0.0187(4) Uani 1 1 d . . . . .
N5 N 0.62018(18) 0.84286(16) 0.26041(7) 0.0152(4) Uani 1 1 d . . . . .
N6 N 0.82830(18) 0.86317(16) 0.26971(6) 0.0151(4) Uani 1 1 d . . . . .
C1 C 0.8581(2) 0.48526(19) 0.36109(8) 0.0175(4) Uani 1 1 d . . . . .
H1 H 0.918980 0.498703 0.340447 0.021 Uiso 1 1 calc R U . . .
C2 C 0.8767(2) 0.39869(19) 0.38765(8) 0.0175(4) Uani 1 1 d . . . . .
H2 H 0.949471 0.355047 0.385204 0.021 Uiso 1 1 calc R U . . .
C3 C 0.7884(2) 0.37356(19) 0.41873(8) 0.0163(4) Uani 1 1 d . . . . .
C4 C 0.6836(2) 0.44398(19) 0.41926(8) 0.0175(4) Uani 1 1 d . . . . .
H4 H 0.619097 0.431470 0.438679 0.021 Uiso 1 1 calc R U . . .
C5 C 0.6740(2) 0.53007(19) 0.39208(8) 0.0159(4) Uani 1 1 d . . . . .
H5 H 0.603671 0.576578 0.394177 0.019 Uiso 1 1 calc R U . . .
C6 C 0.9033(2) 0.22896(19) 0.44815(8) 0.0178(4) Uani 1 1 d . . . . .
C7 C 1.1006(2) 0.1635(2) 0.46802(8) 0.0210(5) Uani 1 1 d . . . . .
C8 C 1.0277(3) 0.0853(2) 0.44897(8) 0.0204(5) Uani 1 1 d . . . . .
C9 C 1.2397(3) 0.1623(2) 0.48526(9) 0.0284(6) Uani 1 1 d . . . . .
H9A H 1.287376 0.211770 0.468288 0.043 Uiso 1 1 calc R U . . .
H9B H 1.274524 0.091563 0.482347 0.043 Uiso 1 1 calc R U . . .
H9C H 1.248287 0.182913 0.516429 0.043 Uiso 1 1 calc R U . . .
C10 C 1.0630(3) -0.0267(2) 0.44146(9) 0.0270(6) Uani 1 1 d . . . . .
H10A H 1.000272 -0.072946 0.453686 0.040 Uiso 1 1 calc R U . . .
H10B H 1.149043 -0.040780 0.456081 0.040 Uiso 1 1 calc R U . . .
H10C H 1.062708 -0.039655 0.409706 0.040 Uiso 1 1 calc R U . . .
C11 C 1.0512(3) 0.3573(2) 0.48770(9) 0.0229(5) Uani 1 1 d . . . . .
H11 H 0.973198 0.401881 0.480426 0.027 Uiso 1 1 calc R U . . .
C12 C 1.0688(3) 0.3469(2) 0.53786(9) 0.0342(7) Uani 1 1 d . . . . .
H12A H 0.994976 0.309489 0.547990 0.051 Uiso 1 1 calc R U . . .
H12B H 1.074664 0.416903 0.551224 0.051 Uiso 1 1 calc R U . . .
H12C H 1.147913 0.307758 0.546590 0.051 Uiso 1 1 calc R U . . .
C13 C 1.1622(3) 0.4124(2) 0.46906(12) 0.0346(7) Uani 1 1 d . . . . .
H13A H 1.242514 0.375232 0.478241 0.052 Uiso 1 1 calc R U . . .
H13B H 1.167998 0.484618 0.480084 0.052 Uiso 1 1 calc R U . . .
H13C H 1.148068 0.413095 0.436754 0.052 Uiso 1 1 calc R U . . .
C14 C 0.8011(3) 0.0703(2) 0.40994(9) 0.0236(5) Uani 1 1 d . . . . .
H14 H 0.830686 -0.003662 0.406593 0.028 Uiso 1 1 calc R U . . .
C15 C 0.6783(3) 0.0660(2) 0.43292(11) 0.0305(6) Uani 1 1 d . . . . .
H15A H 0.639497 0.136011 0.432892 0.046 Uiso 1 1 calc R U . . .
H15B H 0.698365 0.042262 0.463431 0.046 Uiso 1 1 calc R U . . .
H15C H 0.617621 0.016969 0.417277 0.046 Uiso 1 1 calc R U . . .
C16 C 0.7778(3) 0.1166(3) 0.36381(9) 0.0343(7) Uani 1 1 d . . . . .
H16A H 0.740738 0.186870 0.365591 0.051 Uiso 1 1 calc R U . . .
H16B H 0.718077 0.071587 0.345549 0.051 Uiso 1 1 calc R U . . .
H16C H 0.859689 0.121055 0.350569 0.051 Uiso 1 1 calc R U . . .
C17 C 0.7297(2) 0.80483(18) 0.28173(7) 0.0141(4) Uani 1 1 d . . . . .
C18 C 0.6480(2) 0.92885(18) 0.23435(7) 0.0152(4) Uani 1 1 d . . . . .
C19 C 0.7818(2) 0.94130(19) 0.24022(8) 0.0159(4) Uani 1 1 d . . . . .
C20 C 0.8438(2) 1.0199(2) 0.21865(8) 0.0197(5) Uani 1 1 d . . . . .
H20 H 0.934441 1.029255 0.223110 0.024 Uiso 1 1 calc R U . . .
C21 C 0.7668(3) 1.0840(2) 0.19032(9) 0.0232(5) Uani 1 1 d . . . . .
H21 H 0.805894 1.137630 0.174530 0.028 Uiso 1 1 calc R U . . .
C22 C 0.6329(3) 1.0715(2) 0.18440(9) 0.0240(5) Uani 1 1 d . . . . .
H22 H 0.583478 1.117023 0.164715 0.029 Uiso 1 1 calc R U . . .
C23 C 0.5708(2) 0.9948(2) 0.20645(8) 0.0205(5) Uani 1 1 d . . . . .
H23 H 0.479861 0.987239 0.202767 0.025 Uiso 1 1 calc R U . . .
C24 C 0.4927(2) 0.7984(2) 0.26759(8) 0.0180(5) Uani 1 1 d . . . . .
H24 H 0.509435 0.732403 0.284972 0.022 Uiso 1 1 calc R U . . .
C25 C 0.4211(3) 0.8715(2) 0.29602(9) 0.0277(6) Uani 1 1 d . . . . .
H25A H 0.403965 0.938047 0.280432 0.042 Uiso 1 1 calc R U . . .
H25B H 0.473621 0.884584 0.323921 0.042 Uiso 1 1 calc R U . . .
H25C H 0.339381 0.839192 0.302082 0.042 Uiso 1 1 calc R U . . .
C26 C 0.4162(3) 0.7673(3) 0.22471(10) 0.0319(6) Uani 1 1 d . . . . .
H26A H 0.387336 0.830534 0.208350 0.048 Uiso 1 1 calc R U . . .
H26B H 0.341220 0.725787 0.231174 0.048 Uiso 1 1 calc R U . . .
H26C H 0.470694 0.725448 0.206877 0.048 Uiso 1 1 calc R U . . .
C27 C 0.9641(2) 0.8418(2) 0.28572(8) 0.0234(5) Uani 1 1 d . . . . .
H27 H 0.962854 0.778427 0.305023 0.028 Uiso 1 1 calc R U . . .
C28 C 1.0181(3) 0.9284(3) 0.31475(10) 0.0327(6) Uani 1 1 d . . . . .
H28A H 1.024841 0.992205 0.297136 0.049 Uiso 1 1 calc R U . . .
H28B H 1.103765 0.908519 0.328181 0.049 Uiso 1 1 calc R U . . .
H28C H 0.961263 0.941508 0.338004 0.049 Uiso 1 1 calc R U . . .
C29 C 1.0418(2) 0.8115(2) 0.24807(9) 0.0211(5) Uani 1 1 d . . . . .
H29A H 1.002449 0.750245 0.232741 0.032 Uiso 1 1 calc R U . . .
H29B H 1.130102 0.794525 0.259781 0.032 Uiso 1 1 calc R U . . .
H29C H 1.043073 0.870244 0.227330 0.032 Uiso 1 1 calc R U . . .
Cl4 Cl 0.41142(10) 0.28181(8) 0.37932(3) 0.0493(2) Uani 1 1 d . . . . .
Cl5 Cl 0.33235(8) 0.06486(7) 0.37577(3) 0.03932(18) Uani 1 1 d . . . . .
Cl6 Cl 0.14306(9) 0.22628(9) 0.35706(3) 0.0528(3) Uani 1 1 d . . . . .
C31 C 0.3034(3) 0.1901(3) 0.35302(9) 0.0317(6) Uani 1 1 d . . . . .
H31 H 0.318208 0.187350 0.321048 0.038 Uiso 1 1 calc R U . . .
Cl1 Cl 0.48645(10) 0.64188(8) 0.47834(3) 0.0521(2) Uani 1 1 d . . . . .
Cl2 Cl 0.26207(13) 0.70520(13) 0.42165(4) 0.0785(4) Uani 1 1 d . . . . .
Cl3 Cl 0.43401(8) 0.86074(7) 0.46126(3) 0.04265(19) Uani 1 1 d . . . . .
C30 C 0.3652(3) 0.7361(3) 0.46841(10) 0.0338(7) Uani 1 1 d . . . . .
H30 H 0.313893 0.738946 0.494518 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 Br1 2.4225(3) . ?
Pd1 Br2 2.4228(3) . ?
Pd1 N1 2.0879(19) . ?
Pd1 C17 1.954(2) . ?
N1 C1 1.348(3) . ?
N1 C5 1.353(3) . ?
N2 C3 1.347(3) . ?
N2 C6 1.353(3) . ?
N3 C6 1.357(3) . ?
N3 C7 1.403(3) . ?
N3 C11 1.484(3) . ?
N4 C6 1.352(3) . ?
N4 C8 1.398(3) . ?
N4 C14 1.480(3) . ?
N5 C17 1.350(3) . ?
N5 C18 1.400(3) . ?
N5 C24 1.481(3) . ?
N6 C17 1.348(3) . ?
N6 C19 1.396(3) . ?
N6 C27 1.479(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.371(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.418(3) . ?
C3 C4 1.416(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.372(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.351(4) . ?
C7 C9 1.495(4) . ?
C8 C10 1.498(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.526(4) . ?
C11 C13 1.511(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 1.0000 . ?
C14 C15 1.518(4) . ?
C14 C16 1.521(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 C19 1.400(3) . ?
C18 C23 1.395(3) . ?
C19 C20 1.390(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.400(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.382(4) . ?
C23 H23 0.9500 . ?
C24 H24 1.0000 . ?
C24 C25 1.516(4) . ?
C24 C26 1.516(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27 1.0000 . ?
C27 C28 1.491(4) . ?
C27 C29 1.515(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
Cl4 C31 1.762(3) . ?
Cl5 C31 1.756(3) . ?
Cl6 C31 1.751(3) . ?
C31 H31 1.0000 . ?
Cl1 C30 1.750(3) . ?
Cl2 C30 1.746(3) . ?
Cl3 C30 1.765(4) . ?
C30 H30 1.0000 . ?

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
Br1 Pd1 Br2 174.593(11) . . ?
N1 Pd1 Br1 92.55(5) . . ?
N1 Pd1 Br2 92.83(5) . . ?
C17 Pd1 Br1 86.03(7) . . ?
C17 Pd1 Br2 88.60(7) . . ?
C17 Pd1 N1 178.56(9) . . ?
C1 N1 Pd1 120.59(16) . . ?
C1 N1 C5 116.1(2) . . ?
C5 N1 Pd1 123.31(15) . . ?
C3 N2 C6 119.4(2) . . ?
C6 N3 C7 109.2(2) . . ?
C6 N3 C11 121.6(2) . . ?
C7 N3 C11 128.9(2) . . ?
C6 N4 C8 109.3(2) . . ?
C6 N4 C14 125.6(2) . . ?
C8 N4 C14 124.7(2) . . ?
C17 N5 C18 110.00(19) . . ?
C17 N5 C24 121.5(2) . . ?
C18 N5 C24 128.40(19) . . ?
C17 N6 C19 109.94(18) . . ?
C17 N6 C27 122.7(2) . . ?
C19 N6 C27 127.3(2) . . ?
N1 C1 H1 118.0 . . ?
N1 C1 C2 124.0(2) . . ?
C2 C1 H1 118.0 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
N2 C3 C2 125.4(2) . . ?
N2 C3 C4 120.1(2) . . ?
C4 C3 C2 114.6(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
N1 C5 C4 123.8(2) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
N2 C6 N3 127.7(2) . . ?
N4 C6 N2 124.7(2) . . ?
N4 C6 N3 107.1(2) . . ?
N3 C7 C9 123.8(2) . . ?
C8 C7 N3 107.0(2) . . ?
C8 C7 C9 129.1(2) . . ?
N4 C8 C10 123.3(2) . . ?
C7 C8 N4 107.4(2) . . ?
C7 C8 C10 129.2(2) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 H11 106.8 . . ?
N3 C11 C12 110.0(2) . . ?
N3 C11 C13 113.0(2) . . ?
C12 C11 H11 106.8 . . ?
C13 C11 H11 106.8 . . ?
C13 C11 C12 113.1(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14 107.2 . . ?
N4 C14 C15 112.1(2) . . ?
N4 C14 C16 111.0(2) . . ?
C15 C14 H14 107.2 . . ?
C15 C14 C16 111.8(2) . . ?
C16 C14 H14 107.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N5 C17 Pd1 125.97(17) . . ?
N6 C17 Pd1 126.28(16) . . ?
N6 C17 N5 107.7(2) . . ?
C19 C18 N5 105.94(19) . . ?
C23 C18 N5 132.7(2) . . ?
C23 C18 C19 121.4(2) . . ?
N6 C19 C18 106.4(2) . . ?
C20 C19 N6 132.0(2) . . ?
C20 C19 C18 121.6(2) . . ?
C19 C20 H20 121.6 . . ?
C21 C20 C19 116.7(2) . . ?
C21 C20 H20 121.6 . . ?
C20 C21 H21 119.2 . . ?
C20 C21 C22 121.7(2) . . ?
C22 C21 H21 119.2 . . ?
C21 C22 H22 119.2 . . ?
C23 C22 C21 121.7(2) . . ?
C23 C22 H22 119.2 . . ?
C18 C23 H23 121.6 . . ?
C22 C23 C18 116.9(2) . . ?
C22 C23 H23 121.6 . . ?
N5 C24 H24 106.6 . . ?
N5 C24 C25 110.3(2) . . ?
N5 C24 C26 112.3(2) . . ?
C25 C24 H24 106.6 . . ?
C26 C24 H24 106.6 . . ?
C26 C24 C25 113.8(2) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N6 C27 H27 106.0 . . ?
N6 C27 C28 110.8(2) . . ?
N6 C27 C29 111.2(2) . . ?
C28 C27 H27 106.0 . . ?
C28 C27 C29 116.0(2) . . ?
C29 C27 H27 106.0 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
Cl4 C31 H31 108.3 . . ?
Cl5 C31 Cl4 110.25(16) . . ?
Cl5 C31 H31 108.3 . . ?
Cl6 C31 Cl4 111.57(17) . . ?
Cl6 C31 Cl5 109.95(18) . . ?
Cl6 C31 H31 108.3 . . ?
Cl1 C30 Cl3 110.11(17) . . ?
Cl1 C30 H30 108.7 . . ?
Cl2 C30 Cl1 111.40(19) . . ?
Cl2 C30 Cl3 109.22(18) . . ?
Cl2 C30 H30 108.7 . . ?
Cl3 C30 H30 108.7 . . ?

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 C1 C2 178.50(19) . . . . ?
Pd1 N1 C5 C4 -179.93(18) . . . . ?
N1 C1 C2 C3 0.8(4) . . . . ?
N2 C3 C4 C5 180.0(2) . . . . ?
N3 C7 C8 N4 0.2(3) . . . . ?
N3 C7 C8 C10 -179.6(2) . . . . ?
N5 C18 C19 N6 -0.5(3) . . . . ?
N5 C18 C19 C20 179.5(2) . . . . ?
N5 C18 C23 C22 -178.0(2) . . . . ?
N6 C19 C20 C21 178.6(2) . . . . ?
C1 N1 C5 C4 -1.0(3) . . . . ?
C1 C2 C3 N2 178.6(2) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C3 N2 C6 N3 71.4(3) . . . . ?
C3 N2 C6 N4 -117.4(3) . . . . ?
C3 C4 C5 N1 2.1(4) . . . . ?
C5 N1 C1 C2 -0.5(4) . . . . ?
C6 N2 C3 C2 8.6(4) . . . . ?
C6 N2 C3 C4 -173.2(2) . . . . ?
C6 N3 C7 C8 0.3(3) . . . . ?
C6 N3 C7 C9 177.6(2) . . . . ?
C6 N3 C11 C12 108.1(3) . . . . ?
C6 N3 C11 C13 -124.5(3) . . . . ?
C6 N4 C8 C7 -0.6(3) . . . . ?
C6 N4 C8 C10 179.2(2) . . . . ?
C6 N4 C14 C15 -62.9(3) . . . . ?
C6 N4 C14 C16 62.9(3) . . . . ?
C7 N3 C6 N2 171.7(2) . . . . ?
C7 N3 C6 N4 -0.7(3) . . . . ?
C7 N3 C11 C12 -64.4(3) . . . . ?
C7 N3 C11 C13 63.0(3) . . . . ?
C8 N4 C6 N2 -171.9(2) . . . . ?
C8 N4 C6 N3 0.8(3) . . . . ?
C8 N4 C14 C15 124.7(3) . . . . ?
C8 N4 C14 C16 -109.4(3) . . . . ?
C9 C7 C8 N4 -176.9(3) . . . . ?
C9 C7 C8 C10 3.3(5) . . . . ?
C11 N3 C6 N2 -2.1(4) . . . . ?
C11 N3 C6 N4 -174.5(2) . . . . ?
C11 N3 C7 C8 173.6(2) . . . . ?
C11 N3 C7 C9 -9.1(4) . . . . ?
C14 N4 C6 N2 14.8(4) . . . . ?
C14 N4 C6 N3 -172.5(2) . . . . ?
C14 N4 C8 C7 172.8(2) . . . . ?
C14 N4 C8 C10 -7.4(4) . . . . ?
C17 N5 C18 C19 0.8(3) . . . . ?
C17 N5 C18 C23 180.0(3) . . . . ?
C17 N5 C24 C25 105.0(3) . . . . ?
C17 N5 C24 C26 -126.9(3) . . . . ?
C17 N6 C19 C18 0.0(3) . . . . ?
C17 N6 C19 C20 -179.9(3) . . . . ?
C17 N6 C27 C28 -113.3(3) . . . . ?
C17 N6 C27 C29 116.1(3) . . . . ?
C18 N5 C17 Pd1 -178.97(16) . . . . ?
C18 N5 C17 N6 -0.8(3) . . . . ?
C18 N5 C24 C25 -71.4(3) . . . . ?
C18 N5 C24 C26 56.7(3) . . . . ?
C18 C19 C20 C21 -1.3(4) . . . . ?
C19 N6 C17 Pd1 178.63(17) . . . . ?
C19 N6 C17 N5 0.5(3) . . . . ?
C19 N6 C27 C28 68.4(3) . . . . ?
C19 N6 C27 C29 -62.2(3) . . . . ?
C19 C18 C23 C22 1.0(4) . . . . ?
C19 C20 C21 C22 1.3(4) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C21 C22 C23 C18 -1.1(4) . . . . ?
C23 C18 C19 N6 -179.8(2) . . . . ?
C23 C18 C19 C20 0.2(4) . . . . ?
C24 N5 C17 Pd1 4.0(3) . . . . ?
C24 N5 C17 N6 -177.8(2) . . . . ?
C24 N5 C18 C19 177.5(2) . . . . ?
C24 N5 C18 C23 -3.3(4) . . . . ?
C27 N6 C17 Pd1 0.0(3) . . . . ?
C27 N6 C17 N5 -178.1(2) . . . . ?
C27 N6 C19 C18 178.5(2) . . . . ?
C27 N6 C19 C20 -1.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_13
_database_code_depnum_ccdc_archive 'CCDC 2354133'
loop_
_audit_author_name
_audit_author_address
'Michael Seidl'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_audit_creation_date             2024-05-08
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        JHF
_chemical_formula_moiety         'I, C H2 Cl2, C17 H27 N4'
_chemical_formula_sum            'C18 H29 Cl2 I N4'
_chemical_formula_weight         499.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.6460(5)
_cell_length_b                   23.9946(12)
_cell_length_c                   10.3357(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.612(2)
_cell_angle_gamma                90
_cell_volume                     2280.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7264
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      26.90
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.693
_exptl_absorpt_coefficient_mu    1.647
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0717 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.9106.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            64820
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.530
_diffrn_reflns_theta_min         2.215
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5362
_reflns_number_total             6934
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker Apex 4 v2021.4-0'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.768
_refine_diff_density_min         -1.076
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         6934
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0210P)²+2.2440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0795
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C15(H15), C14(H14)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C17(H17A,H17B,H17C), C8(H8A,H8B,
 H8C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.05768(2) 0.63854(2) 0.97452(2) 0.03156(6) Uani 1 1 d . . . . .
Cl2 Cl 0.58112(11) 0.67174(4) 0.58476(11) 0.0664(3) Uani 1 1 d . . . . .
Cl1 Cl 0.65206(15) 0.55839(5) 0.52877(11) 0.0826(3) Uani 1 1 d . . . . .
N1 N 0.2805(2) 0.59049(9) 0.6978(2) 0.0281(4) Uani 1 1 d . . . . .
N3 N 0.3388(2) 0.63183(8) 0.9224(2) 0.0248(4) Uani 1 1 d . . . . .
N4 N -0.0338(2) 0.67763(9) 0.4053(2) 0.0308(5) Uani 1 1 d . . . . .
N2 N 0.2579(2) 0.54668(9) 0.8998(2) 0.0294(4) Uani 1 1 d . . . . .
C12 C 0.1783(3) 0.61971(10) 0.6081(2) 0.0248(5) Uani 1 1 d . . . . .
C1 C 0.2852(3) 0.59070(10) 0.8309(2) 0.0252(5) Uani 1 1 d . . . . .
C13 C 0.1774(3) 0.62081(11) 0.4698(3) 0.0291(5) Uani 1 1 d . . . . .
H13 H 0.250747 0.601382 0.444081 0.035 Uiso 1 1 calc R U . . .
C16 C 0.0629(3) 0.64969(11) 0.6359(3) 0.0301(5) Uani 1 1 d . . . . .
H16 H 0.056094 0.650397 0.725628 0.036 Uiso 1 1 calc R U . . .
C9 C 0.3832(3) 0.68639(11) 0.8830(3) 0.0306(5) Uani 1 1 d . . . . .
H9 H 0.361186 0.685450 0.782080 0.037 Uiso 1 1 calc R U . . .
C3 C 0.3456(3) 0.61261(12) 1.0518(3) 0.0306(5) Uani 1 1 d . . . . .
C15 C -0.0371(3) 0.67719(12) 0.5357(3) 0.0347(6) Uani 1 1 d . . . . .
H15 H -0.112482 0.696928 0.557435 0.042 Uiso 1 1 calc R U . . .
C14 C 0.0732(3) 0.64919(11) 0.3741(3) 0.0306(5) Uani 1 1 d . . . . .
H14 H 0.075554 0.649076 0.282863 0.037 Uiso 1 1 calc R U . . .
C2 C 0.2959(3) 0.55991(12) 1.0373(3) 0.0339(6) Uani 1 1 d . . . . .
C10 C 0.2925(3) 0.73355(12) 0.9138(3) 0.0409(7) Uani 1 1 d . . . . .
H10A H 0.189447 0.723103 0.883034 0.061 Uiso 1 1 calc R U . . .
H10B H 0.306915 0.767371 0.866261 0.061 Uiso 1 1 calc R U . . .
H10C H 0.322631 0.740534 1.011755 0.061 Uiso 1 1 calc R U . . .
C11 C 0.5457(3) 0.69495(14) 0.9404(4) 0.0444(7) Uani 1 1 d . . . . .
H11A H 0.571540 0.700399 1.038777 0.067 Uiso 1 1 calc R U . . .
H11B H 0.574266 0.727889 0.898496 0.067 Uiso 1 1 calc R U . . .
H11C H 0.596438 0.662107 0.920983 0.067 Uiso 1 1 calc R U . . .
C4 C 0.1914(3) 0.49319(11) 0.8407(3) 0.0392(6) Uani 1 1 d . . . . .
H4 H 0.160211 0.473854 0.912992 0.047 Uiso 1 1 calc R U . . .
C17 C -0.1449(4) 0.70870(13) 0.3013(3) 0.0436(7) Uani 1 1 d . . . . .
H17A H -0.241897 0.696719 0.301751 0.065 Uiso 1 1 calc R U . . .
H17B H -0.133419 0.701395 0.211780 0.065 Uiso 1 1 calc R U . . .
H17C H -0.133543 0.748684 0.320930 0.065 Uiso 1 1 calc R U . . .
C8 C 0.3896(4) 0.64687(15) 1.1780(3) 0.0481(8) Uani 1 1 d . . . . .
H8A H 0.479355 0.667098 1.183137 0.072 Uiso 1 1 calc R U . . .
H8B H 0.406065 0.622464 1.257243 0.072 Uiso 1 1 calc R U . . .
H8C H 0.312224 0.673554 1.176533 0.072 Uiso 1 1 calc R U . . .
C6 C 0.0566(4) 0.50159(14) 0.7231(4) 0.0543(9) Uani 1 1 d . . . . .
H6A H -0.001764 0.531679 0.744265 0.081 Uiso 1 1 calc R U . . .
H6B H -0.000433 0.467088 0.706075 0.081 Uiso 1 1 calc R U . . .
H6C H 0.083914 0.511505 0.642078 0.081 Uiso 1 1 calc R U . . .
C18 C 0.6166(4) 0.60315(13) 0.6488(3) 0.0445(7) Uani 1 1 d . . . . .
H18A H 0.701370 0.603510 0.731761 0.053 Uiso 1 1 calc R U . . .
H18B H 0.531590 0.589156 0.673795 0.053 Uiso 1 1 calc R U . . .
C7 C 0.2763(4) 0.52023(15) 1.1419(3) 0.0552(9) Uani 1 1 d . . . . .
H7A H 0.172242 0.514843 1.128917 0.083 Uiso 1 1 calc R U . . .
H7B H 0.322758 0.535472 1.232695 0.083 Uiso 1 1 calc R U . . .
H7C H 0.320993 0.484359 1.132742 0.083 Uiso 1 1 calc R U . . .
C5 C 0.3035(4) 0.45624(15) 0.8096(5) 0.0684(12) Uani 1 1 d . . . . .
H5A H 0.338834 0.473899 0.740041 0.103 Uiso 1 1 calc R U . . .
H5B H 0.259601 0.420139 0.776237 0.103 Uiso 1 1 calc R U . . .
H5C H 0.385114 0.450643 0.892266 0.103 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2 C18 1.768(3) . ?
Cl1 C18 1.751(4) . ?
N1 C12 1.331(3) . ?
N1 C1 1.362(3) . ?
N3 C1 1.356(3) . ?
N3 C9 1.472(3) . ?
N3 C3 1.397(3) . ?
N4 C15 1.358(3) . ?
N4 C14 1.355(4) . ?
N4 C17 1.471(3) . ?
N2 C1 1.344(3) . ?
N2 C2 1.392(3) . ?
N2 C4 1.482(3) . ?
C12 C13 1.428(3) . ?
C12 C16 1.425(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.360(4) . ?
C16 H16 0.9500 . ?
C16 C15 1.354(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.522(4) . ?
C9 C11 1.512(4) . ?
C3 C2 1.344(4) . ?
C3 C8 1.491(4) . ?
C15 H15 0.9500 . ?
C14 H14 0.9500 . ?
C2 C7 1.495(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C4 H4 1.0000 . ?
C4 C6 1.501(4) . ?
C4 C5 1.506(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

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
C12 N1 C1 119.5(2) . . ?
C1 N3 C9 122.4(2) . . ?
C1 N3 C3 108.9(2) . . ?
C3 N3 C9 128.6(2) . . ?
C15 N4 C17 119.9(2) . . ?
C14 N4 C15 118.7(2) . . ?
C14 N4 C17 121.4(2) . . ?
C1 N2 C2 109.2(2) . . ?
C1 N2 C4 126.3(2) . . ?
C2 N2 C4 124.5(2) . . ?
N1 C12 C13 119.1(2) . . ?
N1 C12 C16 125.8(2) . . ?
C16 C12 C13 115.1(2) . . ?
N3 C1 N1 126.6(2) . . ?
N2 C1 N1 125.5(2) . . ?
N2 C1 N3 107.2(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 H13 119.4 . . ?
C12 C16 H16 119.6 . . ?
C15 C16 C12 120.7(2) . . ?
C15 C16 H16 119.6 . . ?
N3 C9 H9 106.3 . . ?
N3 C9 C10 111.7(2) . . ?
N3 C9 C11 111.5(2) . . ?
C10 C9 H9 106.3 . . ?
C11 C9 H9 106.3 . . ?
C11 C9 C10 114.2(2) . . ?
N3 C3 C8 125.0(3) . . ?
C2 C3 N3 107.0(2) . . ?
C2 C3 C8 127.8(3) . . ?
N4 C15 H15 118.7 . . ?
C16 C15 N4 122.5(3) . . ?
C16 C15 H15 118.7 . . ?
N4 C14 C13 121.8(2) . . ?
N4 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
N2 C2 C7 122.7(3) . . ?
C3 C2 N2 107.6(2) . . ?
C3 C2 C7 129.6(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C4 H4 106.5 . . ?
N2 C4 C6 112.2(2) . . ?
N2 C4 C5 110.4(3) . . ?
C6 C4 H4 106.5 . . ?
C6 C4 C5 114.1(3) . . ?
C5 C4 H4 106.5 . . ?
N4 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
N4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Cl2 C18 H18A 109.4 . . ?
Cl2 C18 H18B 109.4 . . ?
Cl1 C18 Cl2 111.28(17) . . ?
Cl1 C18 H18A 109.4 . . ?
Cl1 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 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
N1 C12 C13 C14 178.7(2) . . . . ?
N1 C12 C16 C15 -178.7(3) . . . . ?
N3 C3 C2 N2 -0.3(3) . . . . ?
N3 C3 C2 C7 -178.4(3) . . . . ?
C12 N1 C1 N3 -78.0(3) . . . . ?
C12 N1 C1 N2 112.8(3) . . . . ?
C12 C13 C14 N4 0.1(4) . . . . ?
C12 C16 C15 N4 0.3(4) . . . . ?
C1 N1 C12 C13 177.8(2) . . . . ?
C1 N1 C12 C16 -4.3(4) . . . . ?
C1 N3 C9 C10 117.8(3) . . . . ?
C1 N3 C9 C11 -113.0(3) . . . . ?
C1 N3 C3 C2 0.0(3) . . . . ?
C1 N3 C3 C8 -175.8(3) . . . . ?
C1 N2 C2 C3 0.5(3) . . . . ?
C1 N2 C2 C7 178.7(3) . . . . ?
C1 N2 C4 C6 -48.1(4) . . . . ?
C1 N2 C4 C5 80.4(4) . . . . ?
C13 C12 C16 C15 -0.7(4) . . . . ?
C16 C12 C13 C14 0.6(4) . . . . ?
C9 N3 C1 N1 8.3(4) . . . . ?
C9 N3 C1 N2 179.1(2) . . . . ?
C9 N3 C3 C2 -178.7(2) . . . . ?
C9 N3 C3 C8 5.6(4) . . . . ?
C3 N3 C1 N1 -170.5(2) . . . . ?
C3 N3 C1 N2 0.3(3) . . . . ?
C3 N3 C9 C10 -63.7(3) . . . . ?
C3 N3 C9 C11 65.5(3) . . . . ?
C15 N4 C14 C13 -0.6(4) . . . . ?
C14 N4 C15 C16 0.4(4) . . . . ?
C2 N2 C1 N1 170.4(2) . . . . ?
C2 N2 C1 N3 -0.5(3) . . . . ?
C2 N2 C4 C6 128.8(3) . . . . ?
C2 N2 C4 C5 -102.7(4) . . . . ?
C4 N2 C1 N1 -12.4(4) . . . . ?
C4 N2 C1 N3 176.8(2) . . . . ?
C4 N2 C2 C3 -176.8(2) . . . . ?
C4 N2 C2 C7 1.4(4) . . . . ?
C17 N4 C15 C16 -179.5(3) . . . . ?
C17 N4 C14 C13 179.3(3) . . . . ?
C8 C3 C2 N2 175.3(3) . . . . ?
C8 C3 C2 C7 -2.8(5) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems, Cryostream 800'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_8
_database_code_depnum_ccdc_archive 'CCDC 2354131'
loop_
_audit_author_name
_audit_author_address
'Michael Seidl'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_audit_creation_date             2024-05-08
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H44 Br2 N6 Pd, C H2 Cl2'
_chemical_formula_sum            'C30 H46 Br2 Cl2 N6 Pd'
_chemical_formula_weight         827.85
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   17.7755(4)
_cell_length_b                   18.4999(4)
_cell_length_c                   10.9830(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3611.70(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    183.00
_cell_measurement_theta_max      27.479
_cell_measurement_theta_min      2.292
_shelx_estimated_absorpt_T_max   0.780
_shelx_estimated_absorpt_T_min   0.581
_exptl_absorpt_coefficient_mu    2.902
_exptl_absorpt_correction_T_max  0.6032
_exptl_absorpt_correction_T_min  0.4718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0959 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.7822.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1672
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            87916
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_min         2.292
_diffrn_ambient_temperature      183.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C14'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                7835
_reflns_number_total             8120
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Bruker Apex 4 v2021.4-0'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 3467 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         8120
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0205
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0236P)²+1.9563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0485
_refine_ls_wR_factor_ref         0.0492
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C27(H27), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B), C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C4(H4), C19(H19), C21(H21), C22(H22), C20(H20)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C29(H29A,H29B,H29C), C26(H26A,H26B,H26C), C16(H16A,H16B,
 H16C), C28(H28A,H28B,H28C), C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C25(H25A,
 H25B,H25C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.59346(2) 0.22675(2) 0.46369(2) 0.01923(5) Uani 1 1 d . . . . .
Br1 Br 0.65982(2) 0.26271(2) 0.64810(3) 0.03451(8) Uani 1 1 d . . . . .
Br2 Br 0.53784(2) 0.17681(2) 0.27832(4) 0.03654(9) Uani 1 1 d . . . . .
Cl2 Cl 0.29373(7) 0.29283(10) 0.26316(16) 0.0774(4) Uani 1 1 d . . . . .
Cl1 Cl 0.35095(15) 0.26152(16) 0.50304(17) 0.1243(9) Uani 1 1 d . . . . .
N4 N 0.37475(15) 0.59787(14) 0.3965(3) 0.0265(6) Uani 1 1 d . . . . .
N3 N 0.48634(14) 0.64654(13) 0.4378(3) 0.0269(6) Uani 1 1 d . . . . .
N5 N 0.67953(12) 0.09025(12) 0.4697(3) 0.0208(4) Uani 1 1 d . . . . .
N2 N 0.48301(16) 0.53791(15) 0.3216(3) 0.0285(6) Uani 1 1 d . . . . .
C6 C 0.45012(17) 0.58944(16) 0.3861(3) 0.0223(6) Uani 1 1 d . . . . .
C18 C 0.67699(18) 0.01966(16) 0.5149(3) 0.0238(6) Uani 1 1 d . . . . .
N6 N 0.57505(14) 0.08139(13) 0.5723(3) 0.0233(5) Uani 1 1 d . . . . .
C13 C 0.56578(19) 0.66761(19) 0.4106(3) 0.0331(7) Uani 1 1 d . . . . .
N1 N 0.56394(15) 0.33355(13) 0.4197(2) 0.0221(5) Uani 1 1 d . . . . .
C8 C 0.35823(18) 0.66182(18) 0.4707(4) 0.0341(7) Uani 1 1 d . . . . .
H8A H 0.346235 0.648283 0.555730 0.041 Uiso 1 1 calc R U . . .
H8B H 0.315839 0.689888 0.436305 0.041 Uiso 1 1 calc R U . . .
C1 C 0.54142(17) 0.38124(16) 0.5052(3) 0.0234(6) Uani 1 1 d . . . . .
H1 H 0.544315 0.366921 0.588091 0.028 Uiso 1 1 calc R U . . .
C17 C 0.61741(17) 0.12644(15) 0.5052(3) 0.0214(6) Uani 1 1 d . . . . .
C2 C 0.51451(16) 0.44936(16) 0.4797(3) 0.0239(6) Uani 1 1 d . . . . .
H2 H 0.499598 0.480299 0.544381 0.029 Uiso 1 1 calc R U . . .
C3 C 0.50889(16) 0.47368(16) 0.3574(3) 0.0219(6) Uani 1 1 d . . . . .
C7 C 0.43099(18) 0.70365(16) 0.4635(4) 0.0314(6) Uani 1 1 d . . . . .
H7A H 0.429519 0.739914 0.397297 0.038 Uiso 1 1 calc R U . . .
H7B H 0.442164 0.728309 0.541480 0.038 Uiso 1 1 calc R U . . .
C27 C 0.73849(19) 0.12240(16) 0.3917(3) 0.0273(7) Uani 1 1 d . . . . .
H27 H 0.720947 0.172009 0.369343 0.033 Uiso 1 1 calc R U . . .
C23 C 0.61063(17) 0.01407(16) 0.5811(3) 0.0257(6) Uani 1 1 d . . . . .
C9 C 0.3160(2) 0.5420(2) 0.3728(4) 0.0354(8) Uani 1 1 d . . . . .
C14 C 0.5830(3) 0.7363(2) 0.4865(5) 0.0515(12) Uani 1 1 d . . . . .
H14A H 0.550654 0.775963 0.459314 0.077 Uiso 1 1 calc R U . . .
H14B H 0.635900 0.749848 0.475496 0.077 Uiso 1 1 calc R U . . .
H14C H 0.573516 0.726376 0.572831 0.077 Uiso 1 1 calc R U . . .
C5 C 0.56053(17) 0.35684(16) 0.3035(3) 0.0236(6) Uani 1 1 d . . . . .
H5 H 0.576671 0.324749 0.241191 0.028 Uiso 1 1 calc R U . . .
C29 C 0.81153(18) 0.13141(19) 0.4620(5) 0.0407(8) Uani 1 1 d . . . . .
H29A H 0.830008 0.083860 0.487513 0.061 Uiso 1 1 calc R U . . .
H29B H 0.802579 0.161504 0.533948 0.061 Uiso 1 1 calc R U . . .
H29C H 0.849106 0.154672 0.409736 0.061 Uiso 1 1 calc R U . . .
C4 C 0.53522(17) 0.42393(16) 0.2694(3) 0.0259(6) Uani 1 1 d . . . . .
H4 H 0.535388 0.437107 0.185836 0.031 Uiso 1 1 calc R U . . .
C26 C 0.4988(2) 0.0966(2) 0.7593(4) 0.0469(9) Uani 1 1 d . . . . .
H26A H 0.450932 0.115672 0.789645 0.070 Uiso 1 1 calc R U . . .
H26B H 0.540402 0.125095 0.793028 0.070 Uiso 1 1 calc R U . . .
H26C H 0.504249 0.046042 0.784260 0.070 Uiso 1 1 calc R U . . .
C19 C 0.7270(2) -0.03786(17) 0.5065(4) 0.0345(8) Uani 1 1 d . . . . .
H19 H 0.771989 -0.034310 0.460311 0.041 Uiso 1 1 calc R U . . .
C24 C 0.50029(18) 0.10142(19) 0.6212(3) 0.0311(7) Uani 1 1 d . . . . .
H24 H 0.491192 0.153114 0.599066 0.037 Uiso 1 1 calc R U . . .
C16 C 0.6194(2) 0.6090(2) 0.4533(6) 0.0537(11) Uani 1 1 d . . . . .
H16A H 0.607404 0.595848 0.537569 0.081 Uiso 1 1 calc R U . . .
H16B H 0.671191 0.626965 0.449103 0.081 Uiso 1 1 calc R U . . .
H16C H 0.614173 0.566420 0.400988 0.081 Uiso 1 1 calc R U . . .
C21 C 0.6417(2) -0.10578(19) 0.6351(5) 0.0481(11) Uani 1 1 d . . . . .
H21 H 0.630591 -0.149522 0.676689 0.058 Uiso 1 1 calc R U . . .
C28 C 0.7472(2) 0.0807(2) 0.2741(4) 0.0448(9) Uani 1 1 d . . . . .
H28A H 0.778091 0.108698 0.217152 0.067 Uiso 1 1 calc R U . . .
H28B H 0.697560 0.072109 0.238257 0.067 Uiso 1 1 calc R U . . .
H28C H 0.771749 0.034293 0.290765 0.067 Uiso 1 1 calc R U . . .
C22 C 0.5914(2) -0.04910(18) 0.6422(4) 0.0385(8) Uani 1 1 d . . . . .
H22 H 0.545767 -0.053066 0.686697 0.046 Uiso 1 1 calc R U . . .
C11 C 0.3181(2) 0.4862(2) 0.4758(5) 0.0459(9) Uani 1 1 d . . . . .
H11A H 0.365822 0.459853 0.473083 0.069 Uiso 1 1 calc R U . . .
H11B H 0.276252 0.452205 0.465974 0.069 Uiso 1 1 calc R U . . .
H11C H 0.313382 0.511035 0.554296 0.069 Uiso 1 1 calc R U . . .
C10 C 0.2394(2) 0.5802(3) 0.3726(5) 0.0588(13) Uani 1 1 d . . . . .
H10A H 0.229120 0.599573 0.453887 0.088 Uiso 1 1 calc R U . . .
H10B H 0.200032 0.545545 0.350286 0.088 Uiso 1 1 calc R U . . .
H10C H 0.240196 0.619796 0.313353 0.088 Uiso 1 1 calc R U . . .
C20 C 0.7084(2) -0.1007(2) 0.5685(4) 0.0466(10) Uani 1 1 d . . . . .
H20 H 0.741527 -0.140901 0.565534 0.056 Uiso 1 1 calc R U . . .
C25 C 0.4391(2) 0.0569(3) 0.5603(5) 0.0511(11) Uani 1 1 d . . . . .
H25A H 0.447080 0.005544 0.578320 0.077 Uiso 1 1 calc R U . . .
H25B H 0.441054 0.064425 0.472019 0.077 Uiso 1 1 calc R U . . .
H25C H 0.389832 0.071870 0.591191 0.077 Uiso 1 1 calc R U . . .
C12 C 0.3273(3) 0.5069(3) 0.2491(4) 0.0536(11) Uani 1 1 d . . . . .
H12A H 0.331449 0.544527 0.186640 0.080 Uiso 1 1 calc R U . . .
H12B H 0.284262 0.475663 0.230729 0.080 Uiso 1 1 calc R U . . .
H12C H 0.373454 0.477961 0.250182 0.080 Uiso 1 1 calc R U . . .
C15 C 0.5740(2) 0.6851(3) 0.2772(5) 0.0496(10) Uani 1 1 d . . . . .
H15A H 0.568835 0.640725 0.229277 0.074 Uiso 1 1 calc R U . . .
H15B H 0.623631 0.706449 0.262599 0.074 Uiso 1 1 calc R U . . .
H15C H 0.534832 0.719558 0.253157 0.074 Uiso 1 1 calc R U . . .
C30 C 0.3719(3) 0.2919(3) 0.3596(5) 0.0531(11) Uani 1 1 d . . . . .
H30A H 0.411155 0.260458 0.323774 0.064 Uiso 1 1 calc R U . . .
H30B H 0.392653 0.341412 0.365321 0.064 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 Br1 2.4365(4) . ?
Pd1 Br2 2.4446(4) . ?
Pd1 N1 2.101(2) . ?
Pd1 C17 1.958(3) . ?
Cl2 C30 1.747(5) . ?
Cl1 C30 1.714(5) . ?
N4 C6 1.354(4) . ?
N4 C8 1.466(4) . ?
N4 C9 1.493(4) . ?
N3 C6 1.361(4) . ?
N3 C13 1.495(4) . ?
N3 C7 1.471(4) . ?
N5 C18 1.398(4) . ?
N5 C17 1.349(4) . ?
N5 C27 1.478(4) . ?
N2 C6 1.324(4) . ?
N2 C3 1.334(4) . ?
C18 C23 1.389(5) . ?
C18 C19 1.389(4) . ?
N6 C17 1.343(4) . ?
N6 C23 1.400(4) . ?
N6 C24 1.481(4) . ?
C13 C14 1.550(5) . ?
C13 C16 1.518(5) . ?
C13 C15 1.507(6) . ?
N1 C1 1.349(4) . ?
N1 C5 1.349(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.509(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.377(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.420(4) . ?
C3 C4 1.414(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C27 H27 1.0000 . ?
C27 C29 1.519(5) . ?
C27 C28 1.512(5) . ?
C23 C22 1.390(5) . ?
C9 C11 1.531(6) . ?
C9 C10 1.534(5) . ?
C9 C12 1.518(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C4 1.372(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C4 H4 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C26 C24 1.519(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(5) . ?
C24 H24 1.0000 . ?
C24 C25 1.520(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.380(5) . ?
C21 C20 1.396(6) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C22 H22 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C20 H20 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?

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
Br1 Pd1 Br2 172.440(14) . . ?
N1 Pd1 Br1 93.17(7) . . ?
N1 Pd1 Br2 93.61(7) . . ?
C17 Pd1 Br1 87.71(9) . . ?
C17 Pd1 Br2 85.61(9) . . ?
C17 Pd1 N1 178.10(11) . . ?
C6 N4 C8 109.8(3) . . ?
C6 N4 C9 126.7(3) . . ?
C8 N4 C9 121.1(3) . . ?
C6 N3 C13 124.5(3) . . ?
C6 N3 C7 108.7(2) . . ?
C7 N3 C13 118.9(3) . . ?
C18 N5 C27 127.2(2) . . ?
C17 N5 C18 109.6(2) . . ?
C17 N5 C27 123.2(2) . . ?
C6 N2 C3 129.5(3) . . ?
N4 C6 N3 110.1(3) . . ?
N2 C6 N4 124.4(3) . . ?
N2 C6 N3 125.0(3) . . ?
C23 C18 N5 106.4(3) . . ?
C19 C18 N5 132.2(3) . . ?
C19 C18 C23 121.4(3) . . ?
C17 N6 C23 109.7(2) . . ?
C17 N6 C24 123.2(3) . . ?
C23 N6 C24 127.1(3) . . ?
N3 C13 C14 107.0(3) . . ?
N3 C13 C16 110.2(3) . . ?
N3 C13 C15 110.0(3) . . ?
C16 C13 C14 107.1(3) . . ?
C15 C13 C14 109.1(3) . . ?
C15 C13 C16 113.2(4) . . ?
C1 N1 Pd1 121.9(2) . . ?
C5 N1 Pd1 122.0(2) . . ?
C5 N1 C1 115.9(3) . . ?
N4 C8 H8A 111.3 . . ?
N4 C8 H8B 111.3 . . ?
N4 C8 C7 102.3(3) . . ?
H8A C8 H8B 109.2 . . ?
C7 C8 H8A 111.3 . . ?
C7 C8 H8B 111.3 . . ?
N1 C1 H1 118.0 . . ?
N1 C1 C2 124.1(3) . . ?
C2 C1 H1 118.0 . . ?
N5 C17 Pd1 125.5(2) . . ?
N6 C17 Pd1 126.4(2) . . ?
N6 C17 N5 108.0(2) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
N2 C3 C2 125.9(3) . . ?
N2 C3 C4 119.5(3) . . ?
C4 C3 C2 114.6(3) . . ?
N3 C7 C8 102.4(2) . . ?
N3 C7 H7A 111.3 . . ?
N3 C7 H7B 111.3 . . ?
C8 C7 H7A 111.3 . . ?
C8 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
N5 C27 H27 106.9 . . ?
N5 C27 C29 110.8(3) . . ?
N5 C27 C28 111.3(3) . . ?
C29 C27 H27 106.9 . . ?
C28 C27 H27 106.9 . . ?
C28 C27 C29 113.7(3) . . ?
C18 C23 N6 106.3(3) . . ?
C18 C23 C22 121.6(3) . . ?
C22 C23 N6 132.1(3) . . ?
N4 C9 C11 108.7(3) . . ?
N4 C9 C10 107.6(3) . . ?
N4 C9 C12 111.1(3) . . ?
C11 C9 C10 109.4(3) . . ?
C12 C9 C11 111.8(3) . . ?
C12 C9 C10 108.2(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C5 H5 117.9 . . ?
N1 C5 C4 124.2(3) . . ?
C4 C5 H5 117.9 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
C18 C19 H19 121.4 . . ?
C20 C19 C18 117.2(3) . . ?
C20 C19 H19 121.4 . . ?
N6 C24 C26 111.3(3) . . ?
N6 C24 H24 107.2 . . ?
N6 C24 C25 110.3(3) . . ?
C26 C24 H24 107.2 . . ?
C26 C24 C25 113.3(3) . . ?
C25 C24 H24 107.2 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C21 H21 119.1 . . ?
C22 C21 C20 121.9(3) . . ?
C20 C21 H21 119.1 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C23 C22 H22 121.6 . . ?
C21 C22 C23 116.9(3) . . ?
C21 C22 H22 121.6 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C19 C20 C21 121.1(3) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Cl2 C30 H30A 109.0 . . ?
Cl2 C30 H30B 109.0 . . ?
Cl1 C30 Cl2 112.8(3) . . ?
Cl1 C30 H30A 109.0 . . ?
Cl1 C30 H30B 109.0 . . ?
H30A C30 H30B 107.8 . . ?

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 C1 C2 -173.3(2) . . . . ?
Pd1 N1 C5 C4 174.0(2) . . . . ?
N4 C8 C7 N3 -24.8(4) . . . . ?
N5 C18 C23 N6 0.7(3) . . . . ?
N5 C18 C23 C22 -178.0(3) . . . . ?
N5 C18 C19 C20 176.8(4) . . . . ?
N2 C3 C4 C5 -178.5(3) . . . . ?
C6 N4 C8 C7 19.7(4) . . . . ?
C6 N4 C9 C11 72.3(4) . . . . ?
C6 N4 C9 C10 -169.3(4) . . . . ?
C6 N4 C9 C12 -51.1(5) . . . . ?
C6 N3 C13 C14 178.6(3) . . . . ?
C6 N3 C13 C16 -65.3(4) . . . . ?
C6 N3 C13 C15 60.1(4) . . . . ?
C6 N3 C7 C8 23.1(4) . . . . ?
C6 N2 C3 C2 -7.9(5) . . . . ?
C6 N2 C3 C4 173.5(3) . . . . ?
C18 N5 C17 Pd1 -179.1(2) . . . . ?
C18 N5 C17 N6 0.3(3) . . . . ?
C18 N5 C27 C29 -69.2(4) . . . . ?
C18 N5 C27 C28 58.4(4) . . . . ?
C18 C23 C22 C21 0.7(6) . . . . ?
C18 C19 C20 C21 0.7(6) . . . . ?
N6 C23 C22 C21 -177.6(4) . . . . ?
C13 N3 C6 N4 -159.9(3) . . . . ?
C13 N3 C6 N2 12.1(5) . . . . ?
C13 N3 C7 C8 173.5(3) . . . . ?
N1 C1 C2 C3 0.0(5) . . . . ?
N1 C5 C4 C3 -1.4(5) . . . . ?
C8 N4 C6 N3 -5.8(4) . . . . ?
C8 N4 C6 N2 -177.8(3) . . . . ?
C8 N4 C9 C11 -88.0(4) . . . . ?
C8 N4 C9 C10 30.4(5) . . . . ?
C8 N4 C9 C12 148.7(4) . . . . ?
C1 N1 C5 C4 -0.9(4) . . . . ?
C1 C2 C3 N2 179.2(3) . . . . ?
C1 C2 C3 C4 -2.2(4) . . . . ?
C17 N5 C18 C23 -0.6(4) . . . . ?
C17 N5 C18 C19 -178.5(4) . . . . ?
C17 N5 C27 C29 112.9(3) . . . . ?
C17 N5 C27 C28 -119.6(3) . . . . ?
C17 N6 C23 C18 -0.5(4) . . . . ?
C17 N6 C23 C22 177.9(4) . . . . ?
C17 N6 C24 C26 -120.4(4) . . . . ?
C17 N6 C24 C25 113.0(4) . . . . ?
C2 C3 C4 C5 2.8(4) . . . . ?
C3 N2 C6 N4 -95.4(4) . . . . ?
C3 N2 C6 N3 93.7(4) . . . . ?
C7 N3 C6 N4 -11.6(4) . . . . ?
C7 N3 C6 N2 160.4(3) . . . . ?
C7 N3 C13 C14 33.2(4) . . . . ?
C7 N3 C13 C16 149.3(4) . . . . ?
C7 N3 C13 C15 -85.3(4) . . . . ?
C27 N5 C18 C23 -178.8(3) . . . . ?
C27 N5 C18 C19 3.3(6) . . . . ?
C27 N5 C17 Pd1 -0.8(4) . . . . ?
C27 N5 C17 N6 178.6(3) . . . . ?
C23 C18 C19 C20 -0.9(5) . . . . ?
C23 N6 C17 Pd1 179.5(2) . . . . ?
C23 N6 C17 N5 0.2(3) . . . . ?
C23 N6 C24 C26 63.5(4) . . . . ?
C23 N6 C24 C25 -63.2(4) . . . . ?
C9 N4 C6 N3 -167.9(3) . . . . ?
C9 N4 C6 N2 20.1(5) . . . . ?
C9 N4 C8 C7 -177.0(3) . . . . ?
C5 N1 C1 C2 1.5(4) . . . . ?
C19 C18 C23 N6 178.9(3) . . . . ?
C19 C18 C23 C22 0.2(5) . . . . ?
C24 N6 C17 Pd1 2.8(4) . . . . ?
C24 N6 C17 N5 -176.6(3) . . . . ?
C24 N6 C23 C18 176.0(3) . . . . ?
C24 N6 C23 C22 -5.5(6) . . . . ?
C22 C21 C20 C19 0.2(8) . . . . ?
C20 C21 C22 C23 -0.9(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
