# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

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

data_ml1_pd_rt
_database_code_depnum_ccdc_archive 'CCDC 2116643'
loop_
_audit_author_name
_audit_author_address
'Angshuman Roy Choudhury'
;IISER Mohali
India
;
_audit_update_record             
;
2021-10-19 deposited with the CCDC.	2022-01-07 downloaded from the CCDC.
;
_audit_creation_date             2019-10-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 N2 O2 Pd'
_chemical_formula_sum            'C20 H14 N2 O2 Pd'
_chemical_formula_weight         420.73
_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'
O O 0.0106 0.0060 '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           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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.3533(4)
_cell_length_b                   16.8012(8)
_cell_length_c                   17.7277(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1594.46(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1958
_cell_measurement_temperature    298.0(2)
_cell_measurement_theta_max      23.5700
_cell_measurement_theta_min      2.6030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_unetI/netI     0.1666
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13717
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.763
_diffrn_reflns_theta_min         2.598
_diffrn_ambient_temperature      298.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 118.20   0.30   30.00    --   29.89  54.00 -30.00  624
  2  ω     14.00  39.80   0.30   30.00    --   29.89  54.00 -30.00   86
  3  ω    -69.00  65.10   0.30   30.00    --   29.89  54.00  30.00  447
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0311455000
_diffrn_orient_matrix_UB_12      0.0386684000
_diffrn_orient_matrix_UB_13      0.0130107000
_diffrn_orient_matrix_UB_21      0.0161678000
_diffrn_orient_matrix_UB_22      -0.0151706000
_diffrn_orient_matrix_UB_23      0.0369997000
_diffrn_orient_matrix_UB_31      0.1277791000
_diffrn_orient_matrix_UB_32      -0.0075460000
_diffrn_orient_matrix_UB_33      -0.0078916000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                2352
_reflns_number_total             5493
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.213
_refine_diff_density_min         -0.996
_refine_diff_density_rms         0.122
_refine_ls_abs_structure_details 
;
 Flack x determined using 554 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         5493
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1902
_refine_ls_R_factor_gt           0.0698
_refine_ls_restrained_S_all      0.971
_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)+(0.0532P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1852
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C7(H7), C16(H16), C2(H2), C12(H12), C9(H9), C4(H4), C19(H19),
 C11(H11), C17(H17), C5(H5), C18(H18), C3(H3), C10(H10)
;
_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 0.34296(18) 0.71552(5) 0.30825(5) 0.0507(3) Uani 1 1 d . . . . .
O2 O 0.3534(18) 0.6121(4) 0.3616(4) 0.057(2) Uani 1 1 d . . . . .
O1 O 0.0452(17) 0.6741(4) 0.2534(4) 0.056(2) Uani 1 1 d . . . . .
N1 N 0.342(2) 0.8177(4) 0.2540(5) 0.048(2) Uani 1 1 d . . . . .
N2 N 0.632(2) 0.7591(5) 0.3608(5) 0.047(2) Uani 1 1 d . . . . .
C1 C -0.064(2) 0.7106(6) 0.1969(6) 0.047(2) Uani 1 1 d . . . . .
C15 C 0.728(2) 0.6392(6) 0.4341(6) 0.045(3) Uani 1 1 d . . . . .
C8 C 0.539(2) 0.8683(6) 0.2797(6) 0.046(3) Uani 1 1 d . . . . .
C14 C 0.770(2) 0.7206(7) 0.4083(6) 0.054(3) Uani 1 1 d . . . . .
H14 H 0.907955 0.747155 0.427751 0.065 Uiso 1 1 calc R . . . .
C6 C 0.007(2) 0.7863(7) 0.1687(5) 0.050(3) Uani 1 1 d . . . . .
C20 C 0.525(3) 0.5922(6) 0.4085(6) 0.052(3) Uani 1 1 d . . . . .
C13 C 0.691(2) 0.8390(6) 0.3364(6) 0.049(3) Uani 1 1 d . . . . .
C7 C 0.201(2) 0.8335(6) 0.1977(7) 0.052(3) Uani 1 1 d . . . . .
H7 H 0.230145 0.881648 0.173288 0.062 Uiso 1 1 calc R . . . .
C16 C 0.903(2) 0.6098(6) 0.4844(7) 0.056(3) Uani 1 1 d . . . . .
H16 H 1.035788 0.641979 0.499254 0.067 Uiso 1 1 calc R . . . .
C2 C -0.265(3) 0.6705(7) 0.1625(8) 0.064(4) Uani 1 1 d . . . . .
H2 H -0.312939 0.621049 0.181190 0.077 Uiso 1 1 calc R . . . .
C12 C 0.887(3) 0.8854(6) 0.3643(6) 0.056(3) Uani 1 1 d . . . . .
H12 H 0.992668 0.865689 0.401596 0.067 Uiso 1 1 calc R . . . .
C9 C 0.578(3) 0.9467(7) 0.2529(7) 0.058(3) Uani 1 1 d . . . . .
H9 H 0.472587 0.968400 0.216486 0.069 Uiso 1 1 calc R . . . .
C4 C -0.322(3) 0.7766(7) 0.0729(7) 0.062(3) Uani 1 1 d . . . . .
H4 H -0.404393 0.798544 0.031597 0.074 Uiso 1 1 calc R . . . .
C19 C 0.517(3) 0.5133(6) 0.4395(6) 0.057(3) Uani 1 1 d . . . . .
H19 H 0.388999 0.479515 0.424119 0.069 Uiso 1 1 calc R . . . .
C11 C 0.922(3) 0.9601(7) 0.3358(7) 0.063(4) Uani 1 1 d . . . . .
H11 H 1.052770 0.990971 0.354404 0.075 Uiso 1 1 calc R . . . .
C17 C 0.884(3) 0.5331(7) 0.5131(8) 0.066(4) Uani 1 1 d . . . . .
H17 H 1.001545 0.513652 0.547145 0.079 Uiso 1 1 calc R . . . .
C5 C -0.130(3) 0.8160(7) 0.1067(7) 0.065(4) Uani 1 1 d . . . . .
H5 H -0.085218 0.865562 0.087581 0.078 Uiso 1 1 calc R . . . .
C18 C 0.684(3) 0.4860(7) 0.4894(7) 0.066(4) Uani 1 1 d . . . . .
H18 H 0.666139 0.434843 0.508612 0.079 Uiso 1 1 calc R . . . .
C3 C -0.394(2) 0.7024(7) 0.1017(7) 0.059(3) Uani 1 1 d . . . . .
H3 H -0.526858 0.674761 0.080352 0.070 Uiso 1 1 calc R . . . .
C10 C 0.775(3) 0.9905(7) 0.2819(7) 0.064(4) Uani 1 1 d . . . . .
H10 H 0.805376 1.041517 0.263688 0.077 Uiso 1 1 calc R . . . .


_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 O2 1.978(7) . ?
Pd1 O1 1.993(9) . ?
Pd1 N1 1.968(8) . ?
Pd1 N2 1.949(10) . ?
O2 C20 1.285(14) . ?
O1 C1 1.310(12) . ?
N1 C8 1.428(14) . ?
N1 C7 1.280(14) . ?
N2 C14 1.294(14) . ?
N2 C13 1.444(13) . ?
C1 C6 1.419(15) . ?
C1 C2 1.410(16) . ?
C15 C14 1.459(15) . ?
C15 C20 1.417(16) . ?
C15 C16 1.384(15) . ?
C8 C13 1.383(15) . ?
C8 C9 1.416(14) . ?
C14 H14 0.9300 . ?
C6 C7 1.404(16) . ?
C6 C5 1.411(16) . ?
C20 C19 1.436(14) . ?
C13 C12 1.400(16) . ?
C7 H7 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.389(15) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(16) . ?
C12 H12 0.9300 . ?
C12 C11 1.366(15) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.364(17) . ?
C4 C3 1.401(16) . ?
C19 H19 0.9300 . ?
C19 C18 1.339(16) . ?
C11 H11 0.9300 . ?
C11 C10 1.340(17) . ?
C17 H17 0.9300 . ?
C17 C18 1.398(18) . ?
C5 H5 0.9300 . ?
C18 H18 0.9300 . ?
C3 H3 0.9300 . ?
C10 H10 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
O2 Pd1 O1 87.1(3) . . ?
N1 Pd1 O2 178.3(5) . . ?
N1 Pd1 O1 93.7(4) . . ?
N2 Pd1 O2 94.6(4) . . ?
N2 Pd1 O1 178.3(3) . . ?
N2 Pd1 N1 84.6(4) . . ?
C20 O2 Pd1 123.9(7) . . ?
C1 O1 Pd1 124.4(7) . . ?
C8 N1 Pd1 111.2(7) . . ?
C7 N1 Pd1 124.3(8) . . ?
C7 N1 C8 124.1(9) . . ?
C14 N2 Pd1 125.2(7) . . ?
C14 N2 C13 122.4(11) . . ?
C13 N2 Pd1 112.3(8) . . ?
O1 C1 C6 124.8(10) . . ?
O1 C1 C2 116.6(10) . . ?
C2 C1 C6 118.7(10) . . ?
C20 C15 C14 122.5(10) . . ?
C16 C15 C14 115.7(10) . . ?
C16 C15 C20 121.8(10) . . ?
C13 C8 N1 117.0(9) . . ?
C13 C8 C9 119.3(11) . . ?
C9 C8 N1 123.6(11) . . ?
N2 C14 C15 125.9(10) . . ?
N2 C14 H14 117.0 . . ?
C15 C14 H14 117.0 . . ?
C7 C6 C1 125.1(10) . . ?
C7 C6 C5 118.0(11) . . ?
C5 C6 C1 116.9(11) . . ?
O2 C20 C15 127.7(10) . . ?
O2 C20 C19 117.7(11) . . ?
C15 C20 C19 114.6(11) . . ?
C8 C13 N2 114.8(11) . . ?
C8 C13 C12 120.0(10) . . ?
C12 C13 N2 125.2(11) . . ?
N1 C7 C6 127.2(10) . . ?
N1 C7 H7 116.4 . . ?
C6 C7 H7 116.4 . . ?
C15 C16 H16 119.4 . . ?
C15 C16 C17 121.2(12) . . ?
C17 C16 H16 119.4 . . ?
C1 C2 H2 118.9 . . ?
C3 C2 C1 122.1(11) . . ?
C3 C2 H2 118.9 . . ?
C13 C12 H12 120.5 . . ?
C11 C12 C13 119.0(12) . . ?
C11 C12 H12 120.5 . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.7(12) . . ?
C10 C9 H9 120.6 . . ?
C5 C4 H4 120.7 . . ?
C5 C4 C3 118.6(11) . . ?
C3 C4 H4 120.7 . . ?
C20 C19 H19 118.4 . . ?
C18 C19 C20 123.2(12) . . ?
C18 C19 H19 118.4 . . ?
C12 C11 H11 118.9 . . ?
C10 C11 C12 122.2(12) . . ?
C10 C11 H11 118.9 . . ?
C16 C17 H17 121.0 . . ?
C16 C17 C18 118.1(12) . . ?
C18 C17 H17 121.0 . . ?
C6 C5 H5 117.9 . . ?
C4 C5 C6 124.2(12) . . ?
C4 C5 H5 117.9 . . ?
C19 C18 C17 121.2(11) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C2 C3 C4 119.4(11) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(11) . . ?
C11 C10 H10 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.192
_oxdiff_exptl_absorpt_empirical_full_min 0.660
