Supplementary Material (ESI) for Dalton Transactions
This journal is (c) The Royal Society of Chemistry 2002

data_ana
_database_code_CSD                  179002

_journal_coden_Cambridge      186

loop_
_publ_author_name
'Garcia-Herbosa, Gabriel'
'Arnaiz, Ana'
'Carbayo, Arancha'
'Casares, Juan A.'
'Cuevas, Jose V.'
'Gutierrez-Puebla, Enrique'

_publ_contact_author_name     	'Prof Gabriel Garcia-Herbosa'  
_publ_contact_author_address 
;
Quimica
Universidad de Burgos
Facultad de Ciencias
Burgos
09001
SPAIN
;


_pub_requested_journal 'J. Chem. Soc. Dalton Trans.'


_publ_contact_author_phone          '+34-947-258822'
_publ_contact_author_fax            '+34-947-258831'
_publ_contact_author_email          'gherbosa@ubu.es'

_publ_contact_letter
;
?
;

#==============================================================================

# 3. TITLE AND AUTHOR LIST

_publ_section_title  
;
Revealing Diastereomeric Nature of Pincer Terdentate 
Nitrogen Ligands 2,6-bis(arylaminomethyl)pyridine through Coordination to 
Palladium.
;

#==============================================================================


_publ_section_acknowledgements
;
This work has been supported by th DGICYT (project xxxx)
;


_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
'C21 H23 Cl2 N3 Pd' 
_chemical_formula_weight          494.72 

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' 

_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    P2(1)/n

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

_cell_length_a                    13.731(2) 
_cell_length_b                    9.7092(13) 
_cell_length_c                    17.230(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  110.188(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      2156.0(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     143(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 

_exptl_crystal_description        prismatic 
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.524 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1000 
_exptl_absorpt_coefficient_mu     1.119 
_exptl_absorpt_correction_type    SADABS 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 

_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       143(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Siemens-Bruker SMART CCD'
_diffrn_measurement_method        'Phi and omega scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             5914 
_diffrn_reflns_av_R_equivalents   0.0747 
_diffrn_reflns_av_sigmaI/netI     0.1469 
_diffrn_reflns_limit_h_min        -14 
_diffrn_reflns_limit_h_max        16 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        2 
_diffrn_reflns_limit_l_min        -20 
_diffrn_reflns_limit_l_max        10 
_diffrn_reflns_theta_min          2.63 
_diffrn_reflns_theta_max          26.59 
_reflns_number_total              3279 
_reflns_number_gt                 1940 
_reflns_threshold_expression      >2sigma(I) 

_computing_data_collection        'SMART Simens-Bruker'
_computing_cell_refinement        'SAINT Simens-Bruker'
_computing_data_reduction         'SAINT Simens-Bruker'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'SHELXTL Simens-Bruker' 
_computing_publication_material   'SHELXTL Simens-Bruker'

_refine_special_details 
; 
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
goodness of fit S are based on F^2^, conventional R-factors R are based 
on F, with F set to zero for negative F^2^. The threshold expression of 
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F^2^ are statistically about twice as large as those based on F, and R- 
factors based on ALL data will be even larger. 
; 

_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
'calc w=1/[\s^2^(Fo^2^)+(0.0721P)^2^+18.5465P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3279 
_refine_ls_number_parameters      246 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1421 
_refine_ls_R_factor_gt            0.0747 
_refine_ls_wR_factor_ref          0.1773 
_refine_ls_wR_factor_gt           0.1487 
_refine_ls_goodness_of_fit_ref    0.916 
_refine_ls_restrained_S_all       0.916 
_refine_ls_shift/su_max           0.024 
_refine_ls_shift/su_mean          0.003 

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_symmetry_multiplicity 
_atom_site_calc_flag 
_atom_site_refinement_flags 
_atom_site_disorder_assembly 
_atom_site_disorder_group 
Pd1 Pd 0.12408(7) 0.45524(7) 0.12693(6) 0.0237(3) Uani 1 1 d . . . 
Cl1 Cl 0.1239(2) 0.6827(2) 0.1632(2) 0.0372(8) Uani 1 1 d . . . 
Cl2 Cl 0.1724(2) 0.7332(3) 0.9229(2) 0.0352(8) Uani 1 1 d . . . 
N1 N 0.1246(7) 0.2642(7) 0.0919(6) 0.021(2) Uani 1 1 d . . . 
N2 N 0.0420(7) 0.3679(7) 0.1950(5) 0.021(2) Uani 1 1 d . . . 
H2 H -0.0253 0.3597 0.1576 0.025 Uiso 1 1 calc R . . 
N3 N 0.2090(7) 0.4783(7) 0.0499(5) 0.022(2) Uani 1 1 d . . . 
H3 H 0.1908 0.5619 0.0224 0.026 Uiso 1 1 calc R . . 
C1 C 0.0789(9) 0.2225(9) 0.2131(8) 0.032(3) Uani 1 1 d . . . 
H11 H 0.0256 0.1662 0.2250 0.038 Uiso 1 1 calc R . . 
H12 H 0.1433 0.2197 0.2621 0.038 Uiso 1 1 calc R . . 
C2 C 0.0992(9) 0.1660(10) 0.1388(8) 0.029(3) Uani 1 1 d . . . 
C3 C 0.1013(8) 0.0301(9) 0.1162(7) 0.023(3) Uani 1 1 d . . . 
H31 H 0.0873 -0.0409 0.1488 0.028 Uiso 1 1 calc R . . 
C4 C 0.1234(9) -0.0023(10) 0.0477(8) 0.033(3) Uani 1 1 d . . . 
H41 H 0.1215 -0.0959 0.0311 0.040 Uiso 1 1 calc R . . 
C5 C 0.1489(9) 0.1001(9) 0.0009(7) 0.028(3) Uani 1 1 d . . . 
H51 H 0.1655 0.0773 -0.0468 0.033 Uiso 1 1 calc R . . 
C6 C 0.1493(9) 0.2361(9) 0.0260(8) 0.024(3) Uani 1 1 d . . . 
C7 C 0.1734(9) 0.3637(10) -0.0132(7) 0.028(3) Uani 1 1 d . . . 
H71 H 0.1107 0.3936 -0.0591 0.033 Uiso 1 1 calc R . . 
H72 H 0.2284 0.3434 -0.0365 0.033 Uiso 1 1 calc R . . 
C11 C 0.0299(8) 0.4382(9) 0.2647(7) 0.024(3) Uani 1 1 d . . . 
C12 C -0.0650(9) 0.5004(10) 0.2549(8) 0.033(3) Uani 1 1 d . . . 
H12' H -0.1212 0.4919 0.2041 0.040 Uiso 1 1 calc R . . 
C13 C -0.0770(10) 0.5756(10) 0.3202(8) 0.033(3) Uani 1 1 d . . . 
H13 H -0.1422 0.6172 0.3128 0.039 Uiso 1 1 calc R . . 
C14 C 0.0017(11) 0.5912(11) 0.3941(9) 0.039(4) Uani 1 1 d . . . 
C15 C 0.0944(10) 0.5256(12) 0.4016(8) 0.040(3) Uani 1 1 d . . . 
H15 H 0.1502 0.5322 0.4528 0.048 Uiso 1 1 calc R . . 
C16 C 0.1094(9) 0.4516(12) 0.3387(8) 0.037(3) Uani 1 1 d . . . 
H16 H 0.1747 0.4099 0.3465 0.044 Uiso 1 1 calc R . . 
C17 C -0.0064(12) 0.6814(11) 0.4625(9) 0.058(4) Uani 1 1 d . . . 
H171 H -0.0754 0.6709 0.4668 0.069 Uiso 1 1 calc R . . 
H172 H 0.0041 0.7778 0.4505 0.069 Uiso 1 1 calc R . . 
H173 H 0.0467 0.6544 0.5149 0.069 Uiso 1 1 calc R . . 
C21 C 0.3204(9) 0.4789(10) 0.0938(7) 0.028(3) Uani 1 1 d . . . 
C22 C 0.3649(9) 0.3853(10) 0.1585(7) 0.029(3) Uani 1 1 d . . . 
H22 H 0.3218 0.3207 0.1726 0.035 Uiso 1 1 calc R . . 
C23 C 0.4697(10) 0.3854(10) 0.2016(8) 0.035(3) Uani 1 1 d . . . 
H23 H 0.4982 0.3230 0.2462 0.042 Uiso 1 1 calc R . . 
C24 C 0.5354(10) 0.4783(12) 0.1799(8) 0.041(3) Uani 1 1 d . . . 
C25 C 0.4889(9) 0.5696(11) 0.1165(8) 0.040(3) Uani 1 1 d . . . 
H25 H 0.5314 0.6349 0.1020 0.048 Uiso 1 1 calc R . . 
C26 C 0.3831(10) 0.5704(11) 0.0729(8) 0.038(3) Uani 1 1 d . . . 
H26 H 0.3544 0.6338 0.0289 0.046 Uiso 1 1 calc R . . 
C27 C 0.6505(10) 0.4791(14) 0.2257(9) 0.057(4) Uani 1 1 d . . . 
H271 H 0.6655 0.4336 0.2793 0.069 Uiso 1 1 calc R . . 
H272 H 0.6754 0.5744 0.2343 0.069 Uiso 1 1 calc R . . 
H273 H 0.6856 0.4298 0.1932 0.069 Uiso 1 1 calc R . . 

loop_ 
_atom_site_aniso_label 
_atom_site_aniso_U_11 
_atom_site_aniso_U_22 
_atom_site_aniso_U_33 
_atom_site_aniso_U_23 
_atom_site_aniso_U_13 
_atom_site_aniso_U_12 
Pd1 0.0253(5) 0.0085(3) 0.0388(6) -0.0002(4) 0.0131(4) -0.0003(4) 
Cl1 0.050(2) 0.0083(11) 0.059(2) -0.0026(12) 0.0269(18) -0.0002(11) 
Cl2 0.0322(18) 0.0229(13) 0.046(2) 0.0023(13) 0.0077(16) -0.0021(11) 
N1 0.014(5) 0.016(4) 0.034(7) 0.000(4) 0.008(5) -0.002(3) 
N2 0.022(5) 0.014(4) 0.025(6) 0.002(4) 0.007(5) -0.001(3) 
N3 0.029(5) 0.014(4) 0.019(6) 0.007(4) 0.003(5) -0.002(4) 
C1 0.034(7) 0.008(4) 0.053(9) 0.017(5) 0.012(7) 0.003(5) 
C2 0.018(6) 0.017(5) 0.046(9) 0.005(5) 0.004(6) 0.001(4) 
C3 0.033(7) 0.006(4) 0.023(7) -0.001(5) -0.002(6) -0.009(4) 
C4 0.031(7) 0.009(4) 0.048(10) -0.003(5) -0.001(7) -0.002(4) 
C5 0.025(7) 0.020(5) 0.038(8) -0.013(5) 0.012(6) -0.001(4) 
C6 0.021(7) 0.017(5) 0.039(9) -0.008(5) 0.017(6) 0.003(4) 
C7 0.038(7) 0.020(5) 0.038(8) 0.001(5) 0.030(6) 0.000(5) 
C11 0.022(6) 0.013(5) 0.032(8) -0.001(5) 0.004(6) -0.008(4) 
C12 0.028(7) 0.030(6) 0.040(9) -0.004(5) 0.009(7) -0.003(5) 
C13 0.033(7) 0.026(6) 0.047(9) -0.013(5) 0.024(7) -0.005(5) 
C14 0.047(9) 0.028(6) 0.048(10) -0.008(6) 0.023(8) -0.014(5) 
C15 0.031(7) 0.046(7) 0.040(9) -0.009(7) 0.007(7) -0.013(6) 
C16 0.023(7) 0.045(7) 0.040(9) -0.009(7) 0.008(7) -0.001(6) 
C17 0.089(13) 0.036(7) 0.064(11) -0.024(7) 0.046(10) -0.028(7) 
C21 0.023(6) 0.026(6) 0.040(8) -0.003(5) 0.018(6) -0.003(5) 
C22 0.036(8) 0.020(5) 0.032(8) -0.004(5) 0.011(7) 0.000(5) 
C23 0.042(8) 0.023(5) 0.032(8) 0.009(5) 0.006(7) 0.009(5) 
C24 0.036(8) 0.044(7) 0.041(9) -0.005(6) 0.010(7) -0.002(6) 
C25 0.027(7) 0.039(7) 0.057(10) 0.016(6) 0.017(7) -0.006(5) 
C26 0.042(8) 0.036(7) 0.033(8) 0.014(6) 0.007(7) 0.000(6) 
C27 0.030(8) 0.069(9) 0.068(11) 0.006(8) 0.011(8) -0.006(7) 

_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 N1 1.952(8) . ? 
Pd1 N3 2.059(9) . ? 
Pd1 N2 2.068(9) . ? 
Pd1 Cl1 2.295(2) . ? 
N1 C6 1.320(15) . ? 
N1 C2 1.371(14) . ? 
N2 C11 1.439(14) . ? 
N2 C1 1.497(11) . ? 
N2 H2 0.9300 . ? 
N3 C21 1.453(13) . ? 
N3 C7 1.514(12) . ? 
N3 H3 0.9300 . ? 
C1 C2 1.504(17) . ? 
C1 H11 0.9900 . ? 
C1 H12 0.9900 . ? 
C2 C3 1.379(13) . ? 
C3 C4 1.354(16) . ? 
C3 H31 0.9500 . ? 
C4 C5 1.399(16) . ? 
C4 H41 0.9500 . ? 
C5 C6 1.389(13) . ? 
C5 H51 0.9500 . ? 
C6 C7 1.502(14) . ? 
C7 H71 0.9900 . ? 
C7 H72 0.9900 . ? 
C11 C16 1.368(15) . ? 
C11 C12 1.393(15) . ? 
C12 C13 1.397(16) . ? 
C12 H12 0.9500 . ? 
C13 C14 1.366(17) . ? 
C13 H13 0.9500 . ? 
C14 C15 1.389(18) . ? 
C14 C17 1.503(17) . ? 
C15 C16 1.374(16) . ? 
C15 H15 0.9500 . ? 
C16 H16 0.9500 . ? 
C17 H171 0.9800 . ? 
C17 H172 0.9800 . ? 
C17 H173 0.9800 . ? 
C21 C26 1.370(16) . ? 
C21 C22 1.404(15) . ? 
C22 C23 1.374(16) . ? 
C22 H22 0.9500 . ? 
C23 C24 1.414(18) . ? 
C23 H23 0.9500 . ? 
C24 C25 1.382(16) . ? 
C24 C27 1.503(17) . ? 
C25 C26 1.386(16) . ? 
C25 H25 0.9500 . ? 
C26 H26 0.9500 . ? 
C27 H271 0.9800 . ? 
C27 H272 0.9800 . ? 
C27 H273 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 
N1 Pd1 N3 80.8(4) . . ? 
N1 Pd1 N2 81.2(4) . . ? 
N3 Pd1 N2 162.0(3) . . ? 
N1 Pd1 Cl1 177.7(3) . . ? 
N3 Pd1 Cl1 97.2(2) . . ? 
N2 Pd1 Cl1 100.9(2) . . ? 
C6 N1 C2 123.8(9) . . ? 
C6 N1 Pd1 119.4(7) . . ? 
C2 N1 Pd1 116.7(8) . . ? 
C11 N2 C1 113.7(8) . . ? 
C11 N2 Pd1 121.4(6) . . ? 
C1 N2 Pd1 107.0(7) . . ? 
C11 N2 H2 104.3 . . ? 
C1 N2 H2 104.3 . . ? 
Pd1 N2 H2 104.3 . . ? 
C21 N3 C7 113.5(8) . . ? 
C21 N3 Pd1 113.2(7) . . ? 
C7 N3 Pd1 105.6(6) . . ? 
C21 N3 H3 108.1 . . ? 
C7 N3 H3 108.1 . . ? 
Pd1 N3 H3 108.1 . . ? 
N2 C1 C2 108.4(9) . . ? 
N2 C1 H11 110.0 . . ? 
C2 C1 H11 110.0 . . ? 
N2 C1 H12 110.0 . . ? 
C2 C1 H12 110.0 . . ? 
H11 C1 H12 108.4 . . ? 
N1 C2 C3 117.7(11) . . ? 
N1 C2 C1 114.1(9) . . ? 
C3 C2 C1 128.1(10) . . ? 
C4 C3 C2 120.1(10) . . ? 
C4 C3 H31 119.9 . . ? 
C2 C3 H31 119.9 . . ? 
C3 C4 C5 120.9(9) . . ? 
C3 C4 H41 119.6 . . ? 
C5 C4 H41 119.5 . . ? 
C4 C5 C6 118.1(11) . . ? 
C4 C5 H51 121.0 . . ? 
C6 C5 H51 121.0 . . ? 
N1 C6 C5 119.3(10) . . ? 
N1 C6 C7 112.2(8) . . ? 
C5 C6 C7 128.4(11) . . ? 
C6 C7 N3 110.4(9) . . ? 
C6 C7 H71 109.6 . . ? 
N3 C7 H71 109.6 . . ? 
C6 C7 H72 109.6 . . ? 
N3 C7 H72 109.6 . . ? 
H71 C7 H72 108.1 . . ? 
C16 C11 C12 118.9(11) . . ? 
C16 C11 N2 122.5(10) . . ? 
C12 C11 N2 118.5(10) . . ? 
C13 C12 C11 119.6(11) . . ? 
C13 C12 H12 120.2 . . ? 
C11 C12 H12 120.2 . . ? 
C14 C13 C12 122.3(12) . . ? 
C14 C13 H13 118.9 . . ? 
C12 C13 H13 118.9 . . ? 
C13 C14 C15 116.1(12) . . ? 
C13 C14 C17 123.2(13) . . ? 
C15 C14 C17 120.6(13) . . ? 
C16 C15 C14 123.3(12) . . ? 
C16 C15 H15 118.3 . . ? 
C14 C15 H15 118.3 . . ? 
C11 C16 C15 119.7(12) . . ? 
C11 C16 H16 120.1 . . ? 
C15 C16 H16 120.1 . . ? 
C14 C17 H171 109.5 . . ? 
C14 C17 H172 109.5 . . ? 
H171 C17 H172 109.5 . . ? 
C14 C17 H173 109.5 . . ? 
H171 C17 H173 109.5 . . ? 
H172 C17 H173 109.5 . . ? 
C26 C21 C22 119.2(11) . . ? 
C26 C21 N3 120.7(10) . . ? 
C22 C21 N3 120.1(9) . . ? 
C23 C22 C21 121.1(11) . . ? 
C23 C22 H22 119.4 . . ? 
C21 C22 H22 119.4 . . ? 
C22 C23 C24 120.2(11) . . ? 
C22 C23 H23 119.9 . . ? 
C24 C23 H23 119.9 . . ? 
C25 C24 C23 117.1(11) . . ? 
C25 C24 C27 121.8(12) . . ? 
C23 C24 C27 121.1(12) . . ? 
C24 C25 C26 122.9(11) . . ? 
C24 C25 H25 118.5 . . ? 
C26 C25 H25 118.5 . . ? 
C21 C26 C25 119.4(11) . . ? 
C21 C26 H26 120.3 . . ? 
C25 C26 H26 120.3 . . ? 
C24 C27 H271 109.5 . . ? 
C24 C27 H272 109.5 . . ? 
H271 C27 H272 109.5 . . ? 
C24 C27 H273 109.5 . . ? 
H271 C27 H273 109.5 . . ? 
H272 C27 H273 109.5 . . ? 

_diffrn_measured_fraction_theta_max    0.727 
_diffrn_reflns_theta_full              26.59 
_diffrn_measured_fraction_theta_full   0.727 
_refine_diff_density_max    1.005 
_refine_diff_density_min   -1.503 
_refine_diff_density_rms    0.167