# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_nt0779_Hadi_P
_database_code_depnum_ccdc_archive 'CCDC 2007895'
loop_
_audit_author_name
_audit_author_address
'Nikolay Tumanov'
;University of Namur
Belgium
;
_audit_update_record             
;
2020-06-04 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 Cl N3 O Pd 1+, N O3 1-'
_chemical_formula_sum            'C21 H21 Cl N4 O4 Pd'
_chemical_formula_weight         535.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0681(3)
_cell_length_b                   10.7643(3)
_cell_length_c                   11.5628(4)
_cell_angle_alpha                90.106(3)
_cell_angle_beta                 109.775(3)
_cell_angle_gamma                93.914(3)
_cell_volume                     1059.25(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    6466
_cell_measurement_theta_min      4.1030
_cell_measurement_theta_max      66.6540

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    8.544
_shelx_estimated_absorpt_T_min   0.177
_shelx_estimated_absorpt_T_max   0.381
_exptl_absorpt_correction_T_min  0.218
_exptl_absorpt_correction_T_max  0.395
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur, Ruby, Gemini Ultra
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1856
_diffrn_reflns_number            8646
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.118
_diffrn_reflns_theta_max         67.003
_diffrn_reflns_theta_full        67.003
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3732
_reflns_number_gt                3571
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+0.1312P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3732
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0704
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.70882(2) 0.62744(2) 0.47711(2) 0.03903(9) Uani 1 1 d . . . . .
Cl1 Cl 0.99952(13) 0.28177(9) 0.06666(9) 0.0794(3) Uani 1 1 d . . . . .
O1 O 0.8003(2) 0.46913(17) 0.46079(18) 0.0485(4) Uani 1 1 d . . . . .
N3 N 0.6684(3) 0.5576(2) 0.6273(2) 0.0427(5) Uani 1 1 d . . . . .
N2 N 0.6060(3) 0.7748(2) 0.5226(3) 0.0465(5) Uani 1 1 d . . . . .
H2A H 0.675(5) 0.828(4) 0.564(4) 0.063(11) Uiso 1 1 d . . . . .
H2B H 0.542(5) 0.808(4) 0.458(4) 0.073(12) Uiso 1 1 d . . . . .
O4 O 0.1810(3) 1.0250(2) 0.3149(2) 0.0659(6) Uani 1 1 d . . . . .
N1 N 0.7469(3) 0.6988(2) 0.3278(2) 0.0437(5) Uani 1 1 d . . . . .
N4 N 0.2587(4) 0.9325(2) 0.3368(3) 0.0592(7) Uani 1 1 d . . . . .
O3 O 0.4009(4) 0.9459(3) 0.3568(3) 0.0991(10) Uani 1 1 d . . . . .
C1 C 0.8424(3) 0.4330(2) 0.3697(3) 0.0435(6) Uani 1 1 d . . . . .
C2 C 0.8879(3) 0.3097(3) 0.3704(3) 0.0498(6) Uani 1 1 d . . . . .
H2 H 0.886297 0.258424 0.434675 0.060 Uiso 1 1 calc R U . . .
C20 C 0.5803(3) 0.6247(3) 0.6737(3) 0.0463(6) Uani 1 1 d . . . . .
C10 C 0.6836(4) 0.8576(2) 0.1606(3) 0.0460(6) Uani 1 1 d . . . . .
C5 C 0.8940(4) 0.4594(3) 0.1774(3) 0.0500(6) Uani 1 1 d . . . . .
H5 H 0.896227 0.508878 0.112116 0.060 Uiso 1 1 calc R U . . .
C6 C 0.8461(3) 0.5088(2) 0.2714(3) 0.0441(6) Uani 1 1 d . . . . .
C16 C 0.7281(4) 0.4536(3) 0.6840(3) 0.0503(7) Uani 1 1 d . . . . .
H16 H 0.789250 0.407854 0.651742 0.060 Uiso 1 1 calc R U . . .
C8 C 0.7093(4) 0.8314(2) 0.2947(3) 0.0499(6) Uani 1 1 d . . . . .
H8 H 0.610073 0.843717 0.307991 0.060 Uiso 1 1 calc R U . . .
C3 C 0.9344(4) 0.2642(3) 0.2785(3) 0.0525(7) Uani 1 1 d . . . . .
H3 H 0.964076 0.183035 0.280808 0.063 Uiso 1 1 calc R U . . .
C7 C 0.8038(3) 0.6358(3) 0.2596(3) 0.0473(6) Uani 1 1 d . . . . .
H7 H 0.819626 0.678096 0.194217 0.057 Uiso 1 1 calc R U . . .
C21 C 0.5113(4) 0.7327(3) 0.5984(3) 0.0510(6) Uani 1 1 d . . . . .
H21A H 0.404656 0.708494 0.545664 0.061 Uiso 1 1 calc R U . . .
H21B H 0.507481 0.800654 0.652359 0.061 Uiso 1 1 calc R U . . .
C15 C 0.7986(4) 0.9098(3) 0.1178(3) 0.0578(7) Uani 1 1 d . . . . .
H15 H 0.899536 0.929538 0.172573 0.069 Uiso 1 1 calc R U . . .
C11 C 0.5341(4) 0.8286(3) 0.0762(3) 0.0575(7) Uani 1 1 d . . . . .
H11 H 0.455086 0.793312 0.102835 0.069 Uiso 1 1 calc R U . . .
C4 C 0.9370(4) 0.3400(3) 0.1815(3) 0.0528(7) Uani 1 1 d . . . . .
C9 C 0.8341(5) 0.9187(3) 0.3845(3) 0.0668(9) Uani 1 1 d . . . . .
H9A H 0.844308 0.896510 0.467068 0.100 Uiso 1 1 calc R U . . .
H9B H 0.804361 1.002761 0.371202 0.100 Uiso 1 1 calc R U . . .
H9C H 0.932733 0.912000 0.372012 0.100 Uiso 1 1 calc R U . . .
C19 C 0.5515(4) 0.5891(3) 0.7792(3) 0.0552(7) Uani 1 1 d . . . . .
H19 H 0.491308 0.636350 0.811039 0.066 Uiso 1 1 calc R U . . .
C17 C 0.7008(4) 0.4139(3) 0.7879(3) 0.0591(8) Uani 1 1 d . . . . .
H17 H 0.741185 0.341188 0.824940 0.071 Uiso 1 1 calc R U . . .
C14 C 0.7640(5) 0.9326(3) -0.0059(4) 0.0687(9) Uani 1 1 d . . . . .
H14 H 0.841999 0.967996 -0.033532 0.082 Uiso 1 1 calc R U . . .
C18 C 0.6129(4) 0.4829(3) 0.8368(3) 0.0610(8) Uani 1 1 d . . . . .
H18 H 0.594966 0.458077 0.908194 0.073 Uiso 1 1 calc R U . . .
C13 C 0.6194(6) 0.9044(3) -0.0863(3) 0.0722(10) Uani 1 1 d . . . . .
H13 H 0.598355 0.920374 -0.169155 0.087 Uiso 1 1 calc R U . . .
C12 C 0.5021(5) 0.8522(3) -0.0483(3) 0.0702(10) Uani 1 1 d . . . . .
H12 H 0.402182 0.832789 -0.104747 0.084 Uiso 1 1 calc R U . . .
O2 O 0.1969(5) 0.8298(3) 0.3412(5) 0.1368(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 O1 1.9811(18) . ?
Pd1 N1 2.016(2) . ?
Pd1 N3 2.028(2) . ?
Pd1 N2 2.047(2) . ?
Cl1 C4 1.741(3) . ?
O1 C1 1.302(3) . ?
N3 C20 1.347(4) . ?
N3 C16 1.350(4) . ?
N2 C21 1.473(4) . ?
N2 H2A 0.83(4) . ?
N2 H2B 0.87(4) . ?
O4 N4 1.236(3) . ?
N1 C7 1.292(4) . ?
N1 C8 1.510(3) . ?
N4 O2 1.214(4) . ?
N4 O3 1.229(4) . ?
C1 C6 1.409(4) . ?
C1 C2 1.416(4) . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C20 C19 1.381(4) . ?
C20 C21 1.495(4) . ?
C10 C15 1.384(5) . ?
C10 C11 1.390(5) . ?
C10 C8 1.518(4) . ?
C5 C4 1.364(4) . ?
C5 C6 1.415(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.438(4) . ?
C16 C17 1.370(5) . ?
C16 H16 0.9300 . ?
C8 C9 1.516(5) . ?
C8 H8 0.9800 . ?
C3 C4 1.394(5) . ?
C3 H3 0.9300 . ?
C7 H7 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C15 C14 1.383(5) . ?
C15 H15 0.9300 . ?
C11 C12 1.396(5) . ?
C11 H11 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C19 C18 1.378(5) . ?
C19 H19 0.9300 . ?
C17 C18 1.375(5) . ?
C17 H17 0.9300 . ?
C14 C13 1.341(6) . ?
C14 H14 0.9300 . ?
C18 H18 0.9300 . ?
C13 C12 1.369(6) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?

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 Pd1 N1 92.84(8) . . ?
O1 Pd1 N3 87.95(8) . . ?
N1 Pd1 N3 179.18(8) . . ?
O1 Pd1 N2 168.74(9) . . ?
N1 Pd1 N2 98.41(9) . . ?
N3 Pd1 N2 80.80(9) . . ?
C1 O1 Pd1 127.22(17) . . ?
C20 N3 C16 119.6(3) . . ?
C20 N3 Pd1 115.91(18) . . ?
C16 N3 Pd1 124.5(2) . . ?
C21 N2 Pd1 110.10(17) . . ?
C21 N2 H2A 108(3) . . ?
Pd1 N2 H2A 110(3) . . ?
C21 N2 H2B 106(3) . . ?
Pd1 N2 H2B 112(3) . . ?
H2A N2 H2B 111(4) . . ?
C7 N1 C8 118.5(2) . . ?
C7 N1 Pd1 122.54(19) . . ?
C8 N1 Pd1 118.94(18) . . ?
O2 N4 O3 119.9(3) . . ?
O2 N4 O4 120.9(3) . . ?
O3 N4 O4 119.1(3) . . ?
O1 C1 C6 124.2(2) . . ?
O1 C1 C2 117.6(2) . . ?
C6 C1 C2 118.2(3) . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
N3 C20 C19 120.9(3) . . ?
N3 C20 C21 114.8(2) . . ?
C19 C20 C21 124.2(3) . . ?
C15 C10 C11 118.4(3) . . ?
C15 C10 C8 124.2(3) . . ?
C11 C10 C8 117.5(3) . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 C7 124.0(3) . . ?
C5 C6 C7 116.8(2) . . ?
N3 C16 C17 121.5(3) . . ?
N3 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
N1 C8 C9 108.7(3) . . ?
N1 C8 C10 113.1(2) . . ?
C9 C8 C10 114.1(3) . . ?
N1 C8 H8 106.8 . . ?
C9 C8 H8 106.8 . . ?
C10 C8 H8 106.8 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
N1 C7 C6 128.6(3) . . ?
N1 C7 H7 115.7 . . ?
C6 C7 H7 115.7 . . ?
N2 C21 C20 110.5(2) . . ?
N2 C21 H21A 109.5 . . ?
C20 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C14 C15 C10 120.3(3) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 Cl1 120.2(2) . . ?
C3 C4 Cl1 119.3(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C18 C19 C20 119.3(3) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C16 C17 C18 119.2(3) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C13 C14 C15 120.8(4) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C17 C18 C19 119.5(3) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C12 C11 119.3(4) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Pd1 O1 C1 C6 7.6(4) . . . . ?
Pd1 O1 C1 C2 -172.69(19) . . . . ?
O1 C1 C2 C3 -179.8(3) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C16 N3 C20 C19 0.6(4) . . . . ?
Pd1 N3 C20 C19 -176.9(2) . . . . ?
C16 N3 C20 C21 -175.9(3) . . . . ?
Pd1 N3 C20 C21 6.5(3) . . . . ?
O1 C1 C6 C5 180.0(3) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
O1 C1 C6 C7 0.1(4) . . . . ?
C2 C1 C6 C7 -179.6(3) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C4 C5 C6 C7 179.6(3) . . . . ?
C20 N3 C16 C17 0.3(4) . . . . ?
Pd1 N3 C16 C17 177.6(2) . . . . ?
C7 N1 C8 C9 -105.2(3) . . . . ?
Pd1 N1 C8 C9 74.1(3) . . . . ?
C7 N1 C8 C10 22.5(4) . . . . ?
Pd1 N1 C8 C10 -158.2(2) . . . . ?
C15 C10 C8 N1 -96.0(3) . . . . ?
C11 C10 C8 N1 85.0(3) . . . . ?
C15 C10 C8 C9 28.9(4) . . . . ?
C11 C10 C8 C9 -150.2(3) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C8 N1 C7 C6 -178.9(3) . . . . ?
Pd1 N1 C7 C6 1.8(4) . . . . ?
C1 C6 C7 N1 -5.2(5) . . . . ?
C5 C6 C7 N1 174.9(3) . . . . ?
Pd1 N2 C21 C20 30.5(3) . . . . ?
N3 C20 C21 N2 -24.7(3) . . . . ?
C19 C20 C21 N2 158.9(3) . . . . ?
C11 C10 C15 C14 0.3(4) . . . . ?
C8 C10 C15 C14 -178.8(3) . . . . ?
C15 C10 C11 C12 -0.1(4) . . . . ?
C8 C10 C11 C12 179.0(3) . . . . ?
C6 C5 C4 C3 0.0(5) . . . . ?
C6 C5 C4 Cl1 -178.7(2) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C2 C3 C4 Cl1 178.9(2) . . . . ?
N3 C20 C19 C18 -0.6(4) . . . . ?
C21 C20 C19 C18 175.6(3) . . . . ?
N3 C16 C17 C18 -1.2(5) . . . . ?
C10 C15 C14 C13 -0.3(5) . . . . ?
C16 C17 C18 C19 1.2(5) . . . . ?
C20 C19 C18 C17 -0.4(5) . . . . ?
C15 C14 C13 C12 0.0(5) . . . . ?
C14 C13 C12 C11 0.1(5) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?

_refine_diff_density_max         0.569
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.061



# start Validation Reply Form
_vrf_PLAT244_nt0779_Hadi_P       
;
PROBLEM: Low    'Solvent' Ueq as Compared to Neighbors of         N4 Check 
RESPONSE: Wobbling NO3^-^ anion.
;
_vrf_PLAT911_nt0779_Hadi_P       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.597         47 Report
RESPONSE: These reflections are missing because of the instrument geometry 
limitations.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_har006
_database_code_depnum_ccdc_archive 'CCDC 1989598'
loop_
_audit_author_name
_audit_author_address
'Jason D. Braun'
;University of Manitoba
Canada
;
_audit_update_record             
;
2020-03-11 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 Br N3 O Pd, N O3'
_chemical_formula_sum            'C21 H21 Br N4 O4 Pd'
_chemical_formula_weight         579.73

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'
Br Br -0.2901 2.4595 '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'

_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'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.0780(3)
_cell_length_b                   14.5585(5)
_cell_length_c                   20.1360(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2074.92(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      33.15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.856
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.858
_shelx_estimated_absorpt_T_min   0.443
_shelx_estimated_absorpt_T_max   0.674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5679
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine--focus tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47690
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.460
_diffrn_reflns_theta_max         33.193
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7903
_reflns_number_gt                6941
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0186P)²+0.4140P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.034(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7903
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0533
_refine_ls_wR_factor_gt          0.0508
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.74491(4) 0.77903(2) 0.03354(2) 0.02911(7) Uani 1 1 d . . . . .
C1 C 0.6137(4) 0.46368(19) 0.01591(14) 0.0208(6) Uani 1 1 d . . . . .
C6 C 0.6464(4) 0.5181(2) -0.04073(15) 0.0259(6) Uani 1 1 d . . . . .
H6 H 0.6382 0.4907 -0.0835 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6899(4) 0.6098(2) -0.03571(16) 0.0257(6) Uani 1 1 d . . . . .
H5 H 0.7124 0.6451 -0.0746 0.031 Uiso 1 1 calc R U . . .
C4 C 0.7009(4) 0.6507(2) 0.02646(15) 0.0225(6) Uani 1 1 d . . . . .
C3 C 0.6706(4) 0.60045(19) 0.08269(15) 0.0223(5) Uani 1 1 d . . . . .
H3 H 0.6789 0.6293 0.1249 0.027 Uiso 1 1 calc R U . . .
C2 C 0.6271(4) 0.50576(18) 0.07867(15) 0.0202(5) Uani 1 1 d . . . . .
C7 C 0.5828(5) 0.46013(18) 0.14008(13) 0.0222(5) Uani 1 1 d . . . . .
H7 H 0.5760 0.4983 0.1783 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4845(4) 0.3444(2) 0.21717(15) 0.0241(6) Uani 1 1 d . . . . .
H8 H 0.3815 0.2985 0.2100 0.029 Uiso 1 1 calc R U . . .
C9 C 0.4009(5) 0.4219(2) 0.25914(17) 0.0328(7) Uani 1 1 d . . . . .
H9A H 0.4999 0.4666 0.2698 0.049 Uiso 1 1 calc R U . . .
H9B H 0.3492 0.3964 0.3004 0.049 Uiso 1 1 calc R U . . .
H9C H 0.2998 0.4524 0.2342 0.049 Uiso 1 1 calc R U . . .
C10 C 0.6374(4) 0.2968(2) 0.25615(14) 0.0227(6) Uani 1 1 d . . . . .
C15 C 0.8148(4) 0.3361(3) 0.26545(15) 0.0299(7) Uani 1 1 d . . . . .
H15 H 0.8458 0.3923 0.2440 0.036 Uiso 1 1 calc R U . . .
C14 C 0.9460(4) 0.2931(3) 0.30610(15) 0.0365(8) Uani 1 1 d . . . . .
H14 H 1.0676 0.3196 0.3117 0.044 Uiso 1 1 calc R U . . .
C13 C 0.9024(4) 0.2125(3) 0.33847(14) 0.0321(6) Uani 1 1 d . . . . .
H13 H 0.9934 0.1835 0.3661 0.039 Uiso 1 1 calc R U . . .
C12 C 0.7266(5) 0.1744(2) 0.33053(16) 0.0308(7) Uani 1 1 d . . . . .
H12 H 0.6951 0.1195 0.3535 0.037 Uiso 1 1 calc R U . . .
C11 C 0.5944(4) 0.2153(2) 0.28921(14) 0.0269(5) Uani 1 1 d . . . . .
H11 H 0.4739 0.1876 0.2834 0.032 Uiso 1 1 calc R U . . .
N3 N 0.5869(4) 0.18781(15) 0.00192(13) 0.0222(5) Uani 1 1 d . . . . .
C16 C 0.5715(4) 0.20945(19) -0.06260(13) 0.0246(5) Uani 1 1 d . . . . .
H16 H 0.5626 0.2723 -0.0750 0.030 Uiso 1 1 calc R U . . .
C17 C 0.5682(5) 0.1433(2) -0.11152(16) 0.0281(6) Uani 1 1 d . . . . .
H17 H 0.5570 0.1601 -0.1569 0.034 Uiso 1 1 calc R U . . .
C18 C 0.5815(5) 0.0516(2) -0.09334(15) 0.0301(6) Uani 1 1 d . . . . .
H18 H 0.5777 0.0048 -0.1261 0.036 Uiso 1 1 calc R U . . .
C19 C 0.6002(5) 0.0293(2) -0.02710(17) 0.0293(6) Uani 1 1 d . . . . .
H19 H 0.6113 -0.0330 -0.0137 0.035 Uiso 1 1 calc R U . . .
C20 C 0.6025(4) 0.09963(19) 0.01984(16) 0.0245(6) Uani 1 1 d . . . . .
C21 C 0.6268(6) 0.0817(2) 0.09248(17) 0.0377(8) Uani 1 1 d . . . . .
H21A H 0.5422 0.0309 0.1060 0.045 Uiso 1 1 calc R U . . .
H21B H 0.7585 0.0623 0.1011 0.045 Uiso 1 1 calc R U . . .
N1 N 0.5510(4) 0.37405(16) 0.14988(12) 0.0214(5) Uani 1 1 d . . . . .
N2 N 0.5833(5) 0.16415(16) 0.13277(13) 0.0290(5) Uani 1 1 d . . . . .
H2 H 0.482(4) 0.1594(10) 0.1500(14) 0.035 Uiso 1 1 d R U . . .
H1 H 0.673(4) 0.1659(12) 0.1644(14) 0.035 Uiso 1 1 d R U . . .
O1 O 0.5716(4) 0.37712(13) 0.00699(10) 0.0267(4) Uani 1 1 d . . . . .
N4 N 0.6004(4) 0.40194(17) 0.78733(12) 0.0251(5) Uani 1 1 d . . . . .
Pd1 Pd 0.57390(3) 0.28089(2) 0.07582(2) 0.01958(5) Uani 1 1 d . . . . .
O2A O 0.4449(6) 0.4239(5) 0.7990(3) 0.0581(19) Uani 0.675(9) 1 d . . P A 1
O3A O 0.6922(8) 0.4281(3) 0.7397(2) 0.0507(19) Uani 0.675(9) 1 d . . P A 1
O4A O 0.6874(8) 0.3466(3) 0.8272(2) 0.0533(16) Uani 0.675(9) 1 d . . P A 1
O3B O 0.7603(13) 0.3932(8) 0.7860(6) 0.061(4) Uani 0.325(9) 1 d . . P A 2
O2B O 0.5325(19) 0.4590(6) 0.7417(6) 0.067(5) Uani 0.325(9) 1 d . . P A 2
O4B O 0.4816(19) 0.3666(11) 0.8219(5) 0.062(4) Uani 0.325(9) 1 d . . 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
Br1 C4 1.900(3) . ?
C1 O1 1.307(3) . ?
C1 C6 1.407(4) . ?
C1 C2 1.408(4) . ?
C6 C5 1.375(4) . ?
C5 C4 1.388(4) . ?
C4 C3 1.364(4) . ?
C3 C2 1.415(4) . ?
C2 C7 1.438(4) . ?
C7 N1 1.288(4) . ?
C8 N1 1.498(4) . ?
C8 C10 1.506(4) . ?
C8 C9 1.528(4) . ?
C10 C15 1.392(4) . ?
C10 C11 1.395(4) . ?
C15 C14 1.388(5) . ?
C14 C13 1.377(5) . ?
C13 C12 1.372(5) . ?
C12 C11 1.386(4) . ?
N3 C20 1.338(4) . ?
N3 C16 1.341(4) . ?
N3 Pd1 2.015(2) . ?
C16 C17 1.378(4) . ?
C17 C18 1.387(4) . ?
C18 C19 1.379(5) . ?
C19 C20 1.393(4) . ?
C20 C21 1.495(5) . ?
C21 N2 1.481(4) . ?
N1 Pd1 2.022(2) . ?
N2 Pd1 2.051(2) . ?
O1 Pd1 1.971(2) . ?
N4 O3B 1.139(9) . ?
N4 O2A 1.170(5) . ?
N4 O4B 1.206(9) . ?
N4 O3A 1.220(5) . ?
N4 O4A 1.294(5) . ?
N4 O2B 1.329(10) . ?

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 C1 C6 117.9(3) . . ?
O1 C1 C2 123.9(3) . . ?
C6 C1 C2 118.1(3) . . ?
C5 C6 C1 121.6(3) . . ?
C6 C5 C4 119.7(3) . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 Br1 119.4(2) . . ?
C5 C4 Br1 119.9(2) . . ?
C4 C3 C2 120.6(3) . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 C7 123.8(2) . . ?
C3 C2 C7 116.6(3) . . ?
N1 C7 C2 128.2(3) . . ?
N1 C8 C10 112.2(2) . . ?
N1 C8 C9 114.2(3) . . ?
C10 C8 C9 109.3(3) . . ?
C15 C10 C11 118.9(3) . . ?
C15 C10 C8 121.9(3) . . ?
C11 C10 C8 118.9(2) . . ?
C14 C15 C10 119.8(3) . . ?
C13 C14 C15 120.9(3) . . ?
C12 C13 C14 119.5(3) . . ?
C13 C12 C11 120.5(3) . . ?
C12 C11 C10 120.3(3) . . ?
C20 N3 C16 119.6(3) . . ?
C20 N3 Pd1 116.7(2) . . ?
C16 N3 Pd1 123.63(18) . . ?
N3 C16 C17 122.0(3) . . ?
C16 C17 C18 118.9(3) . . ?
C19 C18 C17 119.2(3) . . ?
C18 C19 C20 119.0(3) . . ?
N3 C20 C19 121.4(3) . . ?
N3 C20 C21 116.1(3) . . ?
C19 C20 C21 122.5(3) . . ?
N2 C21 C20 111.8(3) . . ?
C7 N1 C8 118.2(2) . . ?
C7 N1 Pd1 121.7(2) . . ?
C8 N1 Pd1 119.95(18) . . ?
C21 N2 Pd1 111.8(2) . . ?
C1 O1 Pd1 125.91(18) . . ?
O3B N4 O4B 131.2(11) . . ?
O2A N4 O3A 125.0(5) . . ?
O2A N4 O4A 119.6(5) . . ?
O3A N4 O4A 115.4(4) . . ?
O3B N4 O2B 114.4(10) . . ?
O4B N4 O2B 114.4(10) . . ?
O1 Pd1 N3 87.66(8) . . ?
O1 Pd1 N1 92.36(8) . . ?
N3 Pd1 N1 178.01(12) . . ?
O1 Pd1 N2 169.23(9) . . ?
N3 Pd1 N2 81.61(10) . . ?
N1 Pd1 N2 98.40(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 O3A 0.95 2.62 3.333(5) 132.0 2_664
C7 H7 O3A 0.95 2.32 3.034(5) 131.8 2_664
C8 H8 O4A 1.00 2.63 3.599(6) 163.7 4_456
C16 H16 O1 0.95 2.25 2.815(3) 117.4 .
C16 H16 O4A 0.95 2.41 3.096(6) 128.4 1_554
C16 H16 O4B 0.95 2.56 3.325(16) 138.2 1_554
C19 H19 Br1 0.95 3.05 3.977(3) 166.4 1_545
C21 H21B O2A 0.99 2.41 3.139(7) 129.6 4_556
C21 H21B O4B 0.99 2.44 3.138(13) 126.9 4_556
N2 H2 O4A 0.80 2.13 2.920(6) 166.4 4_456
N2 H2 O3B 0.80 2.17 2.932(10) 159.4 4_456
N2 H1 O2A 0.90 2.44 3.175(7) 139.1 4_556
N2 H1 O4B 0.90 2.25 2.997(12) 140.0 4_556

_refine_diff_density_max         0.763
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.082

