# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2010
data_global
_journal_coden_Cambridge 222
loop_
_publ_author_name
'Christoph Janiak'
'Frederik Blank'
'Venancio Rodriguez'
'Jose Ruiz'
'Harald Scherer'
_publ_contact_author_name 'Christoph Janiak'
_publ_contact_author_email JANIAK@UNI-FREIBURG.DE
_publ_section_title
;
Palladium(II) complexes with pentafluorophenyl ligands:
Structures, C6F5 fluxionality by 2D NMR studies and pre-catalysts for the
vinyl addition polymerization of norbornene
;
# Attachment '1-3-5crystaldata.CIF'
data_pd3
_database_code_depnum_ccdc_archive 'CCDC 757345'
#TrackingRef '1-3-5crystaldata.CIF'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(N,N,N',N'-tetramethylenediamine)-chloro-pentafluorophenyl-palladium(II)
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C12 H16 Cl F5 N2 Pd'
_chemical_formula_sum 'C12 H16 Cl F5 N2 Pd'
_chemical_formula_weight 425.12
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'
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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M 'A b a 2'
_symmetry_space_group_name_Hall 'A 2 -2ac'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z+1/2'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'
_cell_length_a 12.5450(7)
_cell_length_b 19.9097(8)
_cell_length_c 11.9976(8)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 2996.6(3)
_cell_formula_units_Z 8
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9740
_cell_measurement_theta_min 2.56
_cell_measurement_theta_max 25.9
_exptl_crystal_description plate
_exptl_crystal_colour pale-yellow
_exptl_crystal_size_max 0.27
_exptl_crystal_size_mid 0.17
_exptl_crystal_size_min 0.03
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.885
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1680
_exptl_absorpt_coefficient_mu 1.464
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6933
_exptl_absorpt_correction_T_max 0.9574
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(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 'Bruker Smart CCD area diffractometer'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 16309
_diffrn_reflns_av_R_equivalents 0.0558
_diffrn_reflns_av_sigmaI/netI 0.0334
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_k_min -25
_diffrn_reflns_limit_k_max 26
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 2.05
_diffrn_reflns_theta_max 28.10
_reflns_number_total 3408
_reflns_number_gt 3266
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART (Bruker 1997)'
_computing_cell_refinement 'SAINT (Bruker, 2006)'
_computing_data_reduction SAINT
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'DIAMOND (Crystal Impact, 2009)'
_computing_publication_material ?
_publ_section_references
;
Bruker (1997). Smart.
Bruker Analytical X-ray Systems, Madison, Wisconsin, USA.
Bruker (2006). APEX2 (Version 2.1-0) and SAINT.
Bruker Analytical X-ray Systems, Madison, Wisconsin, USA.
Crystal Impact (2009). DIAMOND. Version3.2c. Crystal Impact GbR, Bonn,
Germany.
Sheldrick, G. M. (1996). SADABS. University of G\"ottingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.
Sheldrick, G. M. (2008). SHELXS97 and SHELXL97. University of
G\"ottingen, Germany.
;
_publ_section_exptl_refinement
;
Hydrogen atoms for aromatic CH, aliphatic CH, CH~2~ and methyl groups
were positioned geometrically (C---H = 0.94 \%A for
aromatic CH, C---H = 0.99 \%A for aliphatic CH, C---H = 0.98 \%A for CH~2~,
C---H = 0.97 \%A for CH~3~) and refined using a
riding model (AFIX 43 for aromatic CH, AFIX 13 for aliphatic CH,
AFIX 23 for CH~2~, AFIX 33 or 137 for CH~3~),
with U~iso~(H) = 1.2U~eq~(CH) and U~iso~(H) = 1.5U~eq~(CH~3~).
The ethylene moiety of the tmeda ligand was refined with equally occupied
split positions for the \l and \d conformers.
The structure was refined in a twin-refinement with a BASF-scale factor
to a near racemic twin.
An attempted solution and refinement in the super-group Cmca (Cmce) did
not give satisfactory results but gave two positions for each ligand
around the Pd atom on the special position (0 y z).
PLATON also did not suggest a space group change but confirmed the present
space group Aba2 (now called Aea2)
The three largest residual Fourier peaks (2.28, 1.96 and 0.64) are all
found within 0.83 \%A of the Pd atom. The deepest hole (-0.44) is 1.23
\%A from the Pd atom.
;
_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^)+(0.0493P)^2^+0.0000P] 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 constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.45(3)
_refine_ls_number_reflns 3408
_refine_ls_number_parameters 209
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0344
_refine_ls_R_factor_gt 0.0326
_refine_ls_wR_factor_ref 0.0763
_refine_ls_wR_factor_gt 0.0753
_refine_ls_goodness_of_fit_ref 1.081
_refine_ls_restrained_S_all 1.080
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd Pd 0.875946(17) 0.810155(11) 0.68079(4) 0.01747(8) Uani 1 1 d . A .
Cl Cl 0.75636(7) 0.75754(4) 0.56434(9) 0.02434(18) Uani 1 1 d . . .
C1 C 0.8247(3) 0.89787(19) 0.6207(4) 0.0247(8) Uani 1 1 d . . .
C2 C 0.8687(3) 0.9285(2) 0.5285(4) 0.0307(9) Uani 1 1 d . . .
C3 C 0.8316(4) 0.9872(2) 0.4819(4) 0.0344(10) Uani 1 1 d . . .
C4 C 0.7428(4) 1.0173(2) 0.5288(4) 0.0407(12) Uani 1 1 d . . .
C5 C 0.6950(4) 0.9885(2) 0.6214(4) 0.0380(11) Uani 1 1 d . . .
C6 C 0.7360(3) 0.93031(19) 0.6648(4) 0.0285(9) Uani 1 1 d . . .
F1 F 0.9558(2) 0.90079(14) 0.4793(2) 0.0390(7) Uani 1 1 d . . .
F2 F 0.8756(3) 1.01545(15) 0.3928(3) 0.0522(8) Uani 1 1 d . . .
F3 F 0.7035(3) 1.07444(14) 0.4844(3) 0.0564(9) Uani 1 1 d . . .
F4 F 0.6075(2) 1.01783(16) 0.6641(3) 0.0589(10) Uani 1 1 d . . .
F5 F 0.68810(19) 0.90446(13) 0.7568(2) 0.0365(6) Uani 1 1 d . . .
N1 N 0.9329(3) 0.71828(17) 0.7478(3) 0.0282(7) Uani 1 1 d . . .
C7 C 0.9811(4) 0.6754(2) 0.6626(5) 0.0392(12) Uani 1 1 d . A .
H7A H 1.0036 0.6329 0.6965 0.059 Uiso 1 1 calc R . .
H7B H 1.0432 0.6981 0.6305 0.059 Uiso 1 1 calc R . .
H7C H 0.9288 0.6664 0.6038 0.059 Uiso 1 1 calc R . .
C8 C 0.8475(5) 0.6793(2) 0.8017(5) 0.0462(13) Uani 1 1 d . A .
H8A H 0.7940 0.6667 0.7459 0.069 Uiso 1 1 calc R . .
H8B H 0.8139 0.7066 0.8599 0.069 Uiso 1 1 calc R . .
H8C H 0.8777 0.6386 0.8351 0.069 Uiso 1 1 calc R . .
C9A C 1.0367(7) 0.7384(4) 0.8059(9) 0.0296(17) Uani 0.50 1 d P A 1
H9A H 1.0590 0.7023 0.8577 0.036 Uiso 0.50 1 calc PR A 1
H9B H 1.0937 0.7446 0.7498 0.036 Uiso 0.50 1 calc PR A 1
C10A C 1.0213(9) 0.7997(5) 0.8666(9) 0.030(2) Uani 0.50 1 d P A 1
H10A H 1.0889 0.8130 0.9031 0.036 Uiso 0.50 1 calc PR A 1
H10B H 0.9670 0.7929 0.9253 0.036 Uiso 0.50 1 calc PR A 1
C9B C 0.9892(6) 0.7386(4) 0.8556(7) 0.0200(14) Uani 0.50 1 d P A 2
H9C H 1.0316 0.7009 0.8860 0.024 Uiso 0.50 1 calc PR A 2
H9D H 0.9371 0.7533 0.9127 0.024 Uiso 0.50 1 calc PR A 2
C10B C 1.0613(7) 0.7967(4) 0.8200(8) 0.0196(16) Uani 0.50 1 d P A 2
H10C H 1.1058 0.7835 0.7556 0.024 Uiso 0.50 1 calc PR A 2
H10D H 1.1086 0.8102 0.8821 0.024 Uiso 0.50 1 calc PR A 2
N2 N 0.9850(3) 0.85547(15) 0.7876(3) 0.0269(7) Uani 1 1 d . . .
C11 C 0.9328(4) 0.8966(3) 0.8719(4) 0.0456(14) Uani 1 1 d . A .
H11A H 0.9864 0.9148 0.9231 0.068 Uiso 1 1 calc R . .
H11B H 0.8819 0.8691 0.9138 0.068 Uiso 1 1 calc R . .
H11C H 0.8949 0.9337 0.8356 0.068 Uiso 1 1 calc R . .
C12 C 1.0651(4) 0.8971(3) 0.7274(4) 0.0426(12) Uani 1 1 d . A .
H12A H 1.0295 0.9359 0.6934 0.064 Uiso 1 1 calc R . .
H12B H 1.0990 0.8701 0.6691 0.064 Uiso 1 1 calc R . .
H12C H 1.1193 0.9128 0.7801 0.064 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
Pd 0.01650(12) 0.02052(13) 0.01540(12) -0.00037(15) -0.00104(12) 0.00100(8)
Cl 0.0201(4) 0.0310(4) 0.0219(4) -0.0047(4) -0.0069(3) -0.0010(3)
C1 0.0256(19) 0.0217(18) 0.0268(19) -0.0019(15) -0.0094(15) 0.0021(14)
C2 0.036(2) 0.028(2) 0.028(2) -0.0001(17) -0.0063(16) 0.0009(17)
C3 0.053(3) 0.024(2) 0.026(2) 0.0028(16) -0.018(2) -0.0034(18)
C4 0.053(3) 0.022(2) 0.046(3) -0.0017(18) -0.029(2) 0.0057(19)
C5 0.035(2) 0.031(2) 0.048(3) -0.008(2) -0.019(2) 0.0129(18)
C6 0.0252(16) 0.0298(18) 0.031(3) -0.0032(17) -0.0058(17) 0.0032(14)
F1 0.0480(16) 0.0368(15) 0.0321(14) 0.0065(11) 0.0094(12) 0.0049(12)
F2 0.087(2) 0.0350(16) 0.0346(16) 0.0128(13) -0.0071(15) -0.0097(14)
F3 0.077(2) 0.0329(14) 0.0596(19) 0.0038(14) -0.0357(17) 0.0173(14)
F4 0.0478(16) 0.0599(18) 0.069(3) -0.0079(19) -0.0109(17) 0.0341(13)
F5 0.0266(13) 0.0424(14) 0.0404(14) -0.0020(12) 0.0053(11) 0.0074(10)
N1 0.0346(19) 0.0204(16) 0.0296(18) -0.0043(13) -0.0128(15) -0.0005(13)
C7 0.029(2) 0.033(2) 0.055(4) 0.001(2) 0.019(2) 0.0058(15)
C8 0.068(3) 0.037(3) 0.034(3) 0.011(2) 0.023(3) 0.015(2)
C9A 0.033(5) 0.029(4) 0.028(5) 0.002(4) -0.012(4) 0.003(4)
C10A 0.040(6) 0.028(5) 0.022(5) -0.005(4) -0.021(4) 0.003(4)
C9B 0.022(4) 0.023(4) 0.015(4) 0.004(3) -0.005(3) -0.002(3)
C10B 0.024(4) 0.022(4) 0.013(4) -0.003(3) -0.004(3) 0.001(3)
N2 0.0291(17) 0.0207(15) 0.0308(19) 0.0023(12) -0.0113(13) -0.0033(13)
C11 0.035(3) 0.075(4) 0.027(3) -0.023(2) -0.002(2) -0.015(2)
C12 0.034(2) 0.059(3) 0.036(2) -0.016(2) 0.0019(19) -0.018(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
Pd C1 1.995(4) . ?
Pd N2 2.081(3) . ?
Pd N1 2.122(3) . ?
Pd Cl 2.3022(10) . ?
C1 C2 1.379(6) . ?
C1 C6 1.391(6) . ?
C2 F1 1.359(5) . ?
C2 C3 1.376(6) . ?
C3 F2 1.329(6) . ?
C3 C4 1.384(7) . ?
C4 F3 1.350(5) . ?
C4 C5 1.386(7) . ?
C5 F4 1.344(5) . ?
C5 C6 1.371(6) . ?
C6 F5 1.358(5) . ?
N1 C7 1.463(6) . ?
N1 C8 1.473(6) . ?
N1 C9B 1.528(8) . ?
N1 C9A 1.530(9) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9A C10A 1.434(13) . ?
C9A H9A 0.9900 . ?
C9A H9B 0.9900 . ?
C10A N2 1.529(9) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C9B C10B 1.529(12) . ?
C9B H9C 0.9900 . ?
C9B H9D 0.9900 . ?
C10B N2 1.561(8) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
N2 C11 1.457(6) . ?
N2 C12 1.489(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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 Pd N2 93.14(14) . . ?
C1 Pd N1 178.48(14) . . ?
N2 Pd N1 85.35(12) . . ?
C1 Pd Cl 88.24(11) . . ?
N2 Pd Cl 178.62(9) . . ?
N1 Pd Cl 93.27(9) . . ?
C2 C1 C6 114.8(4) . . ?
C2 C1 Pd 123.3(3) . . ?
C6 C1 Pd 121.8(3) . . ?
F1 C2 C3 116.1(4) . . ?
F1 C2 C1 119.4(4) . . ?
C3 C2 C1 124.5(4) . . ?
F2 C3 C2 123.1(5) . . ?
F2 C3 C4 118.6(4) . . ?
C2 C3 C4 118.3(4) . . ?
F3 C4 C3 119.9(5) . . ?
F3 C4 C5 120.4(5) . . ?
C3 C4 C5 119.7(4) . . ?
F4 C5 C6 121.9(5) . . ?
F4 C5 C4 118.7(4) . . ?
C6 C5 C4 119.4(4) . . ?
F5 C6 C5 117.6(4) . . ?
F5 C6 C1 119.1(3) . . ?
C5 C6 C1 123.3(5) . . ?
C7 N1 C8 107.5(3) . . ?
C7 N1 C9B 123.7(4) . . ?
C8 N1 C9B 96.0(5) . . ?
C7 N1 C9A 96.9(5) . . ?
C8 N1 C9A 123.9(5) . . ?
C9B N1 C9A 32.0(4) . . ?
C7 N1 Pd 112.2(3) . . ?
C8 N1 Pd 112.1(3) . . ?
C9B N1 Pd 104.4(3) . . ?
C9A N1 Pd 103.5(4) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10A C9A N1 109.9(7) . . ?
C10A C9A H9A 109.7 . . ?
N1 C9A H9A 109.7 . . ?
C10A C9A H9B 109.7 . . ?
N1 C9A H9B 109.7 . . ?
H9A C9A H9B 108.2 . . ?
C9A C10A N2 110.1(8) . . ?
C9A C10A H10A 109.6 . . ?
N2 C10A H10A 109.6 . . ?
C9A C10A H10B 109.6 . . ?
N2 C10A H10B 109.6 . . ?
H10A C10A H10B 108.2 . . ?
N1 C9B C10B 103.7(6) . . ?
N1 C9B H9C 111.0 . . ?
C10B C9B H9C 111.0 . . ?
N1 C9B H9D 111.0 . . ?
C10B C9B H9D 111.0 . . ?
H9C C9B H9D 109.0 . . ?
C9B C10B N2 105.9(6) . . ?
C9B C10B H10C 110.6 . . ?
N2 C10B H10C 110.5 . . ?
C9B C10B H10D 110.5 . . ?
N2 C10B H10D 110.5 . . ?
H10C C10B H10D 108.7 . . ?
C11 N2 C12 109.1(3) . . ?
C11 N2 C10A 96.4(5) . . ?
C12 N2 C10A 120.2(6) . . ?
C11 N2 C10B 121.6(5) . . ?
C12 N2 C10B 97.2(5) . . ?
C10A N2 C10B 28.2(4) . . ?
C11 N2 Pd 112.1(3) . . ?
C12 N2 Pd 112.7(2) . . ?
C10A N2 Pd 105.2(4) . . ?
C10B N2 Pd 103.4(3) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
_diffrn_measured_fraction_theta_max 0.950
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 2.279
_refine_diff_density_min -0.439
_refine_diff_density_rms 0.113
#===END
data_yo
_database_code_depnum_ccdc_archive 'CCDC 757346'
#TrackingRef '1-3-5crystaldata.CIF'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(2,2'-bipyridine)-chloro-pentafluorophenyl-palladium(II)
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C16 H8 Cl F5 N2 Pd'
_chemical_formula_sum 'C16 H8 Cl F5 N2 Pd'
_chemical_formula_weight 465.09
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'
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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M 'P b c a'
_symmetry_space_group_name_Hall ?
loop_
_symmetry_equiv_pos_as_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'
'-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 7.0364(3)
_cell_length_b 16.9602(7)
_cell_length_c 25.4701(11)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 3039.6(2)
_cell_formula_units_Z 8
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9999
_cell_measurement_theta_min 2.40
_cell_measurement_theta_max 28.04
_exptl_crystal_description needle
_exptl_crystal_colour pale-yellow
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 2.033
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1808
_exptl_absorpt_coefficient_mu 1.454
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6534
_exptl_absorpt_correction_T_max 0.8926
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(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 'Bruker Smart CCD area diffractometer'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 32576
_diffrn_reflns_av_R_equivalents 0.0260
_diffrn_reflns_av_sigmaI/netI 0.0150
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 22
_diffrn_reflns_limit_l_min -33
_diffrn_reflns_limit_l_max 33
_diffrn_reflns_theta_min 1.60
_diffrn_reflns_theta_max 28.22
_reflns_number_total 3596
_reflns_number_gt 3357
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART (Bruker 1997)'
_computing_cell_refinement 'SAINT (Bruker, 2006)'
_computing_data_reduction SAINT
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'DIAMOND (Crystal Impact, 2009)'
_computing_publication_material ?
_publ_section_references
;
Bruker (1997). Smart.
Bruker Analytical X-ray Systems, Madison, Wisconsin, USA.
Bruker (2006). APEX2 (Version 2.1-0) and SAINT.
Bruker Analytical X-ray Systems, Madison, Wisconsin, USA.
Crystal Impact (2009). DIAMOND. Version3.2c. Crystal Impact GbR, Bonn,
Germany.
Sheldrick, G. M. (1996). SADABS. University of G\"ottingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.
Sheldrick, G. M. (2008). SHELXS97 and SHELXL97. University of
G\"ottingen, Germany.
;
_publ_section_exptl_refinement
;
Hydrogen atoms for aromatic CH, aliphatic CH, CH~2~ and methyl groups
were positioned geometrically (C---H = 0.94 \%A for
aromatic CH, C---H = 0.99 \%A for aliphatic CH, C---H = 0.98 \%A for CH~2~,
C---H = 0.97 \%A for CH~3~) and refined using a
riding model (AFIX 43 for aromatic CH, AFIX 13 for aliphatic CH,
AFIX 23 for CH~2~, AFIX 33 or 137 for CH~3~),
with U~iso~(H) = 1.2U~eq~(CH) and U~iso~(H) = 1.5U~eq~(CH~3~).
;
_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^)+(0.0285P)^2^+3.5253P] 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 constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3596
_refine_ls_number_parameters 226
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0284
_refine_ls_R_factor_gt 0.0257
_refine_ls_wR_factor_ref 0.0619
_refine_ls_wR_factor_gt 0.0606
_refine_ls_goodness_of_fit_ref 1.114
_refine_ls_restrained_S_all 1.114
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd Pd 0.60065(2) 0.230067(9) 0.174549(6) 0.01395(6) Uani 1 1 d . . .
Cl Cl 0.60246(8) 0.35170(3) 0.21227(2) 0.02274(12) Uani 1 1 d . . .
C1 C 0.5756(3) 0.28449(12) 0.10481(8) 0.0170(4) Uani 1 1 d . . .
C2 C 0.4139(3) 0.32610(13) 0.09112(9) 0.0197(4) Uani 1 1 d . . .
C3 C 0.3953(3) 0.36838(14) 0.04489(9) 0.0227(5) Uani 1 1 d . . .
C4 C 0.5442(3) 0.37051(13) 0.00975(8) 0.0219(4) Uani 1 1 d . . .
C5 C 0.7075(3) 0.32912(13) 0.02125(8) 0.0211(4) Uani 1 1 d . . .
C6 C 0.7195(3) 0.28768(12) 0.06780(8) 0.0191(4) Uani 1 1 d . . .
F1 F 0.26165(19) 0.32735(9) 0.12371(5) 0.0281(3) Uani 1 1 d . . .
F2 F 0.2334(2) 0.40737(9) 0.03362(6) 0.0352(4) Uani 1 1 d . . .
F3 F 0.5297(2) 0.41171(8) -0.03502(5) 0.0313(3) Uani 1 1 d . . .
F4 F 0.8536(2) 0.33064(9) -0.01280(6) 0.0335(3) Uani 1 1 d . . .
F5 F 0.88637(19) 0.24953(9) 0.07676(5) 0.0276(3) Uani 1 1 d . . .
N1 N 0.6117(2) 0.16931(10) 0.24528(7) 0.0153(3) Uani 1 1 d . . .
C7 C 0.6230(3) 0.20064(13) 0.29342(8) 0.0191(4) Uani 1 1 d . . .
H7 H 0.6324 0.2563 0.2969 0.023 Uiso 1 1 calc R . .
C8 C 0.6213(3) 0.15453(14) 0.33830(9) 0.0213(4) Uani 1 1 d . . .
H8 H 0.6301 0.1782 0.3720 0.026 Uiso 1 1 calc R . .
C9 C 0.6067(3) 0.07391(14) 0.33336(9) 0.0222(5) Uani 1 1 d . . .
H9 H 0.6034 0.0414 0.3637 0.027 Uiso 1 1 calc R . .
C10 C 0.5970(3) 0.04060(13) 0.28367(9) 0.0198(4) Uani 1 1 d . . .
H10 H 0.5894 -0.0150 0.2795 0.024 Uiso 1 1 calc R . .
C11 C 0.5986(3) 0.08990(12) 0.24009(8) 0.0161(4) Uani 1 1 d . . .
N2 N 0.6016(2) 0.11700(10) 0.14759(7) 0.0153(3) Uani 1 1 d . . .
C12 C 0.6042(3) 0.09418(13) 0.09713(9) 0.0189(4) Uani 1 1 d . . .
H12 H 0.6153 0.1332 0.0705 0.023 Uiso 1 1 calc R . .
C13 C 0.5913(3) 0.01583(13) 0.08257(9) 0.0222(5) Uani 1 1 d . . .
H13 H 0.5957 0.0014 0.0466 0.027 Uiso 1 1 calc R . .
C14 C 0.5721(3) -0.04103(13) 0.12078(9) 0.0225(5) Uani 1 1 d . . .
H14 H 0.5591 -0.0950 0.1115 0.027 Uiso 1 1 calc R . .
C15 C 0.5721(3) -0.01834(13) 0.17316(8) 0.0193(4) Uani 1 1 d . . .
H15 H 0.5601 -0.0567 0.2001 0.023 Uiso 1 1 calc R . .
C16 C 0.5898(3) 0.06101(13) 0.18578(8) 0.0160(4) Uani 1 1 d . . .
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
Pd 0.01608(9) 0.01141(9) 0.01435(9) 0.00077(5) -0.00059(5) 0.00010(5)
Cl 0.0321(3) 0.0130(2) 0.0231(3) -0.00229(19) 0.0024(2) -0.0004(2)
C1 0.0214(10) 0.0129(9) 0.0166(10) -0.0001(8) -0.0010(8) -0.0014(8)
C2 0.0203(10) 0.0204(10) 0.0185(10) 0.0026(8) 0.0025(8) 0.0003(8)
C3 0.0243(11) 0.0214(11) 0.0224(11) 0.0048(9) -0.0021(9) 0.0050(9)
C4 0.0327(12) 0.0191(10) 0.0139(10) 0.0042(8) -0.0006(9) -0.0015(9)
C5 0.0239(11) 0.0222(10) 0.0172(10) -0.0012(8) 0.0064(9) -0.0031(9)
C6 0.0189(10) 0.0160(9) 0.0225(10) -0.0017(8) -0.0015(8) 0.0008(8)
F1 0.0221(7) 0.0364(8) 0.0257(7) 0.0121(6) 0.0069(6) 0.0078(6)
F2 0.0326(8) 0.0432(9) 0.0300(7) 0.0164(7) 0.0013(6) 0.0163(7)
F3 0.0426(8) 0.0333(8) 0.0180(7) 0.0108(6) 0.0014(6) 0.0027(7)
F4 0.0325(8) 0.0418(8) 0.0263(7) 0.0066(6) 0.0120(6) 0.0020(7)
F5 0.0203(7) 0.0339(7) 0.0285(8) 0.0050(7) 0.0028(5) 0.0077(6)
N1 0.0136(8) 0.0151(8) 0.0170(8) -0.0002(7) -0.0003(6) 0.0008(6)
C7 0.0197(10) 0.0181(10) 0.0194(10) -0.0010(8) 0.0000(8) 0.0007(8)
C8 0.0215(10) 0.0271(12) 0.0154(10) -0.0015(9) 0.0017(8) 0.0010(9)
C9 0.0215(11) 0.0268(12) 0.0183(10) 0.0057(9) 0.0018(8) 0.0008(9)
C10 0.0202(10) 0.0174(10) 0.0219(11) 0.0032(8) -0.0002(8) -0.0012(8)
C11 0.0123(9) 0.0178(10) 0.0182(10) -0.0001(8) -0.0005(7) 0.0005(7)
N2 0.0150(8) 0.0138(8) 0.0169(9) 0.0000(7) -0.0023(6) 0.0006(6)
C12 0.0209(10) 0.0175(10) 0.0182(10) -0.0001(8) -0.0019(8) -0.0003(8)
C13 0.0279(12) 0.0208(10) 0.0180(10) -0.0048(9) -0.0012(9) -0.0006(9)
C14 0.0260(11) 0.0158(10) 0.0256(11) -0.0037(9) 0.0002(9) 0.0000(9)
C15 0.0218(10) 0.0133(10) 0.0227(11) 0.0019(8) 0.0002(8) 0.0021(8)
C16 0.0127(9) 0.0170(10) 0.0183(10) 0.0012(8) -0.0006(7) 0.0012(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
Pd C1 2.010(2) . ?
Pd N2 2.0368(17) . ?
Pd N1 2.0768(18) . ?
Pd Cl 2.2757(5) . ?
C1 C2 1.384(3) . ?
C1 C6 1.384(3) . ?
C2 F1 1.355(2) . ?
C2 C3 1.385(3) . ?
C3 F2 1.348(3) . ?
C3 C4 1.378(3) . ?
C4 F3 1.341(2) . ?
C4 C5 1.378(3) . ?
C5 F4 1.345(2) . ?
C5 C6 1.381(3) . ?
C6 F5 1.360(2) . ?
N1 C7 1.339(3) . ?
N1 C11 1.356(3) . ?
C7 C8 1.385(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 C16 1.469(3) . ?
N2 C12 1.342(3) . ?
N2 C16 1.362(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
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 Pd N2 97.74(8) . . ?
C1 Pd N1 176.31(8) . . ?
N2 Pd N1 79.93(7) . . ?
C1 Pd Cl 87.56(6) . . ?
N2 Pd Cl 174.70(5) . . ?
N1 Pd Cl 94.78(5) . . ?
C2 C1 C6 114.21(19) . . ?
C2 C1 Pd 121.93(16) . . ?
C6 C1 Pd 123.77(16) . . ?
F1 C2 C1 120.25(19) . . ?
F1 C2 C3 115.97(19) . . ?
C1 C2 C3 123.8(2) . . ?
F2 C3 C4 119.4(2) . . ?
F2 C3 C2 121.0(2) . . ?
C4 C3 C2 119.6(2) . . ?
F3 C4 C5 120.6(2) . . ?
F3 C4 C3 120.5(2) . . ?
C5 C4 C3 118.8(2) . . ?
F4 C5 C4 119.37(19) . . ?
F4 C5 C6 121.1(2) . . ?
C4 C5 C6 119.5(2) . . ?
F5 C6 C5 116.04(19) . . ?
F5 C6 C1 119.91(19) . . ?
C5 C6 C1 124.0(2) . . ?
C7 N1 C11 119.17(18) . . ?
C7 N1 Pd 126.85(15) . . ?
C11 N1 Pd 113.93(14) . . ?
N1 C7 C8 122.1(2) . . ?
N1 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 119.4(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C11 118.9(2) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
N1 C11 C10 121.3(2) . . ?
N1 C11 C16 115.21(18) . . ?
C10 C11 C16 123.45(19) . . ?
C12 N2 C16 118.92(18) . . ?
C12 N2 Pd 126.47(15) . . ?
C16 N2 Pd 114.55(14) . . ?
N2 C12 C13 122.2(2) . . ?
N2 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 119.0(2) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C16 119.4(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
N2 C16 C15 121.0(2) . . ?
N2 C16 C11 115.94(18) . . ?
C15 C16 C11 123.02(19) . . ?
_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.478
_refine_diff_density_min -0.329
_refine_diff_density_rms 0.083
#===END
data_vrff1s
_database_code_depnum_ccdc_archive 'CCDC 757347'
#TrackingRef '1-3-5crystaldata.CIF'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
{bis(3,5-dimethylpyrazolyl)methane}-chloro-pentafluorophenyl-palladium(II)
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C17 H16 Cl F5 N4 Pd'
_chemical_formula_sum 'C17 H16 Cl F5 N4 Pd'
_chemical_formula_weight 513.19
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'
F F 0.0171 0.0103 '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)/c
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 7.1660(3)
_cell_length_b 17.2246(6)
_cell_length_c 15.2372(6)
_cell_angle_alpha 90.00
_cell_angle_beta 96.7630(10)
_cell_angle_gamma 90.00
_cell_volume 1867.66(13)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9582
_cell_measurement_theta_min 2.36
_cell_measurement_theta_max 28.16
_exptl_crystal_description prism
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.17
_exptl_crystal_size_mid 0.16
_exptl_crystal_size_min 0.05
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.825
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1016
_exptl_absorpt_coefficient_mu 1.195
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.8227
_exptl_absorpt_correction_T_max 0.9427
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(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 'Bruker Smart CCD area diffractometer'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 20956
_diffrn_reflns_av_R_equivalents 0.0279
_diffrn_reflns_av_sigmaI/netI 0.0223
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 22
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 1.79
_diffrn_reflns_theta_max 27.15
_reflns_number_total 4116
_reflns_number_gt 3846
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART (Bruker 1997)'
_computing_cell_refinement 'SAINT (Bruker, 2006)'
_computing_data_reduction SAINT
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'DIAMOND (Crystal Impact, 2009)'
_computing_publication_material ?
_publ_section_references
;
Bruker (1997). Smart.
Bruker Analytical X-ray Systems, Madison, Wisconsin, USA.
Bruker (2006). APEX2 (Version 2.1-0) and SAINT.
Bruker Analytical X-ray Systems, Madison, Wisconsin, USA.
Crystal Impact (2009). DIAMOND. Version3.2c. Crystal Impact GbR, Bonn,
Germany.
Sheldrick, G. M. (1996). SADABS. University of G\"ottingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.
Sheldrick, G. M. (2008). SHELXS97 and SHELXL97. University of
G\"ottingen, Germany.
;
_publ_section_exptl_refinement
;
Hydrogen atoms for aromatic CH, aliphatic CH, CH~2~ and methyl groups
were positioned geometrically (C---H = 0.94 \%A for
aromatic CH, C---H = 0.99 \%A for aliphatic CH, C---H = 0.98 \%A for CH~2~,
C---H = 0.97 \%A for CH~3~) and refined using a
riding model (AFIX 43 for aromatic CH, AFIX 13 for aliphatic CH,
AFIX 23 for CH~2~, AFIX 33 or 137 for CH~3~),
with U~iso~(H) = 1.2U~eq~(CH) and U~iso~(H) = 1.5U~eq~(CH~3~).
;
_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^)+(0.0356P)^2^+3.4764P] 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 constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 4116
_refine_ls_number_parameters 253
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0319
_refine_ls_R_factor_gt 0.0293
_refine_ls_wR_factor_ref 0.0744
_refine_ls_wR_factor_gt 0.0728
_refine_ls_goodness_of_fit_ref 1.067
_refine_ls_restrained_S_all 1.067
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd Pd 0.22862(3) 0.318141(11) 0.243496(12) 0.01079(7) Uani 1 1 d . . .
Cl Cl 0.44359(9) 0.33772(4) 0.36559(4) 0.01620(13) Uani 1 1 d . . .
C1 C 0.2022(4) 0.43277(15) 0.22699(17) 0.0138(5) Uani 1 1 d . . .
C2 C 0.1590(4) 0.48772(15) 0.28802(17) 0.0161(5) Uani 1 1 d . . .
C3 C 0.1541(4) 0.56665(16) 0.27165(18) 0.0181(5) Uani 1 1 d . . .
C4 C 0.1914(4) 0.59447(16) 0.1907(2) 0.0216(6) Uani 1 1 d . . .
C5 C 0.2331(4) 0.54230(17) 0.12759(19) 0.0224(6) Uani 1 1 d . . .
C6 C 0.2392(4) 0.46388(16) 0.14669(17) 0.0172(5) Uani 1 1 d . . .
F1 F 0.1158(2) 0.46564(9) 0.36837(10) 0.0229(4) Uani 1 1 d . . .
F2 F 0.1149(3) 0.61680(9) 0.33479(12) 0.0262(4) Uani 1 1 d . . .
F3 F 0.1901(3) 0.67120(10) 0.17511(13) 0.0333(4) Uani 1 1 d . . .
F4 F 0.2718(3) 0.56780(11) 0.04805(12) 0.0358(5) Uani 1 1 d . . .
F5 F 0.2878(3) 0.41658(10) 0.08194(10) 0.0232(4) Uani 1 1 d . . .
N1 N 0.3056(3) 0.16799(12) 0.15831(14) 0.0134(4) Uani 1 1 d . . .
N2 N 0.2819(3) 0.19710(13) 0.24009(14) 0.0136(4) Uani 1 1 d . . .
C7 C 0.3008(4) 0.13671(15) 0.29508(17) 0.0157(5) Uani 1 1 d . . .
C8 C 0.3377(4) 0.06915(16) 0.24825(18) 0.0191(5) Uani 1 1 d . . .
H8 H 0.3582 0.0185 0.2721 0.023 Uiso 1 1 calc R . .
C9 C 0.3385(4) 0.09051(15) 0.16144(18) 0.0168(5) Uani 1 1 d . . .
C10 C 0.2834(4) 0.14493(17) 0.39129(18) 0.0217(6) Uani 1 1 d . . .
H10A H 0.2575 0.1993 0.4046 0.033 Uiso 1 1 calc R . .
H10B H 0.4010 0.1287 0.4258 0.033 Uiso 1 1 calc R . .
H10C H 0.1802 0.1122 0.4067 0.033 Uiso 1 1 calc R . .
C11 C 0.3707(5) 0.04394(17) 0.08195(19) 0.0274(7) Uani 1 1 d . . .
H11A H 0.3619 0.0779 0.0300 0.041 Uiso 1 1 calc R . .
H11B H 0.2753 0.0030 0.0725 0.041 Uiso 1 1 calc R . .
H11C H 0.4959 0.0203 0.0911 0.041 Uiso 1 1 calc R . .
C12 C 0.2734(4) 0.21921(15) 0.08277(16) 0.0130(5) Uani 1 1 d . . .
H12A H 0.3631 0.2631 0.0901 0.016 Uiso 1 1 calc R . .
H12B H 0.2948 0.1906 0.0285 0.016 Uiso 1 1 calc R . .
N3 N 0.0831(3) 0.24874(12) 0.07397(14) 0.0122(4) Uani 1 1 d . . .
N4 N 0.0349(3) 0.29844(12) 0.13765(14) 0.0128(4) Uani 1 1 d . . .
C13 C -0.1484(4) 0.31156(15) 0.11851(18) 0.0155(5) Uani 1 1 d . . .
C14 C -0.2173(4) 0.27037(15) 0.04233(17) 0.0156(5) Uani 1 1 d . . .
H14 H -0.3429 0.2704 0.0142 0.019 Uiso 1 1 calc R . .
C15 C -0.0685(4) 0.23003(14) 0.01609(16) 0.0132(5) Uani 1 1 d . . .
C16 C -0.2531(4) 0.36243(18) 0.1750(2) 0.0249(6) Uani 1 1 d . . .
H16A H -0.1663 0.3829 0.2240 0.037 Uiso 1 1 calc R . .
H16B H -0.3519 0.3322 0.1985 0.037 Uiso 1 1 calc R . .
H16C H -0.3101 0.4056 0.1395 0.037 Uiso 1 1 calc R . .
C17 C -0.0585(4) 0.17359(16) -0.05735(18) 0.0190(6) Uani 1 1 d . . .
H17A H 0.0713 0.1555 -0.0570 0.029 Uiso 1 1 calc R . .
H17B H -0.0997 0.1989 -0.1139 0.029 Uiso 1 1 calc R . .
H17C H -0.1404 0.1292 -0.0494 0.029 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
Pd 0.01288(11) 0.01023(11) 0.00917(11) -0.00070(6) 0.00100(7) 0.00021(7)
Cl 0.0168(3) 0.0184(3) 0.0126(3) -0.0015(2) -0.0016(2) -0.0006(2)
C1 0.0136(12) 0.0116(12) 0.0158(12) -0.0004(9) 0.0000(10) -0.0005(9)
C2 0.0184(13) 0.0165(13) 0.0133(12) 0.0007(10) 0.0019(10) -0.0003(10)
C3 0.0178(13) 0.0144(12) 0.0219(14) -0.0049(10) 0.0015(11) 0.0007(10)
C4 0.0241(14) 0.0119(12) 0.0278(15) 0.0040(11) -0.0002(12) -0.0001(11)
C5 0.0282(15) 0.0218(14) 0.0171(13) 0.0065(11) 0.0027(11) -0.0022(12)
C6 0.0200(13) 0.0171(13) 0.0144(13) -0.0015(10) 0.0017(10) -0.0002(10)
F1 0.0361(10) 0.0184(8) 0.0163(8) -0.0011(6) 0.0118(7) 0.0001(7)
F2 0.0346(10) 0.0146(8) 0.0301(9) -0.0088(7) 0.0067(8) 0.0019(7)
F3 0.0491(12) 0.0123(8) 0.0383(11) 0.0066(7) 0.0046(9) 0.0006(8)
F4 0.0600(13) 0.0264(10) 0.0230(9) 0.0122(8) 0.0132(9) -0.0015(9)
F5 0.0359(10) 0.0211(8) 0.0140(8) -0.0005(6) 0.0084(7) 0.0011(7)
N1 0.0160(11) 0.0139(10) 0.0104(10) -0.0012(8) 0.0018(8) 0.0032(8)
N2 0.0156(11) 0.0149(10) 0.0103(10) -0.0014(8) 0.0008(8) 0.0011(8)
C7 0.0180(13) 0.0148(12) 0.0138(12) 0.0027(10) -0.0008(10) -0.0007(10)
C8 0.0244(14) 0.0134(12) 0.0187(13) 0.0013(10) -0.0008(11) 0.0016(11)
C9 0.0171(13) 0.0139(12) 0.0188(13) -0.0016(10) -0.0007(10) 0.0035(10)
C10 0.0302(16) 0.0218(14) 0.0129(13) 0.0039(10) 0.0014(11) -0.0010(12)
C11 0.0423(18) 0.0190(14) 0.0199(14) -0.0049(11) -0.0006(13) 0.0120(13)
C12 0.0133(12) 0.0134(12) 0.0123(12) 0.0006(9) 0.0018(9) 0.0024(9)
N3 0.0136(10) 0.0112(10) 0.0119(10) -0.0012(8) 0.0023(8) 0.0023(8)
N4 0.0159(11) 0.0119(10) 0.0108(10) -0.0022(8) 0.0032(8) 0.0024(8)
C13 0.0158(12) 0.0160(12) 0.0152(12) 0.0009(10) 0.0036(10) 0.0010(10)
C14 0.0131(12) 0.0180(13) 0.0152(12) 0.0010(10) -0.0005(10) 0.0012(10)
C15 0.0161(12) 0.0137(12) 0.0096(11) 0.0016(9) 0.0005(9) -0.0014(9)
C16 0.0173(14) 0.0323(16) 0.0249(15) -0.0102(13) 0.0023(12) 0.0075(12)
C17 0.0189(13) 0.0214(14) 0.0167(13) -0.0046(11) 0.0014(11) -0.0002(11)
_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
Pd C1 1.996(3) . ?
Pd N4 2.029(2) . ?
Pd N2 2.121(2) . ?
Pd Cl 2.2963(6) . ?
C1 C2 1.387(4) . ?
C1 C6 1.390(4) . ?
C2 F1 1.352(3) . ?
C2 C3 1.382(4) . ?
C3 F2 1.347(3) . ?
C3 C4 1.379(4) . ?
C4 F3 1.343(3) . ?
C4 C5 1.374(4) . ?
C5 F4 1.348(3) . ?
C5 C6 1.381(4) . ?
C6 F5 1.356(3) . ?
N1 C9 1.355(3) . ?
N1 N2 1.372(3) . ?
N1 C12 1.447(3) . ?
N2 C7 1.333(3) . ?
C7 C8 1.406(4) . ?
C7 C10 1.493(4) . ?
C8 C9 1.374(4) . ?
C8 H8 0.9500 . ?
C9 C11 1.493(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 . ?
C12 N3 1.447(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
N3 C15 1.355(3) . ?
N3 N4 1.368(3) . ?
N4 C13 1.331(3) . ?
C13 C14 1.400(4) . ?
C13 C16 1.491(4) . ?
C14 C15 1.371(4) . ?
C14 H14 0.9500 . ?
C15 C17 1.490(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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 Pd N4 91.12(10) . . ?
C1 Pd N2 169.59(10) . . ?
N4 Pd N2 85.66(8) . . ?
C1 Pd Cl 90.08(8) . . ?
N4 Pd Cl 178.31(6) . . ?
N2 Pd Cl 93.37(6) . . ?
C2 C1 C6 114.1(2) . . ?
C2 C1 Pd 128.0(2) . . ?
C6 C1 Pd 117.86(19) . . ?
F1 C2 C3 115.9(2) . . ?
F1 C2 C1 120.5(2) . . ?
C3 C2 C1 123.6(2) . . ?
F2 C3 C4 119.7(2) . . ?
F2 C3 C2 120.3(2) . . ?
C4 C3 C2 120.0(3) . . ?
F3 C4 C5 121.2(3) . . ?
F3 C4 C3 120.2(3) . . ?
C5 C4 C3 118.7(3) . . ?
F4 C5 C4 120.0(3) . . ?
F4 C5 C6 120.2(3) . . ?
C4 C5 C6 119.7(3) . . ?
F5 C6 C5 116.0(2) . . ?
F5 C6 C1 120.0(2) . . ?
C5 C6 C1 123.9(3) . . ?
C9 N1 N2 111.6(2) . . ?
C9 N1 C12 129.7(2) . . ?
N2 N1 C12 118.3(2) . . ?
C7 N2 N1 105.7(2) . . ?
C7 N2 Pd 139.21(18) . . ?
N1 N2 Pd 115.04(16) . . ?
N2 C7 C8 109.8(2) . . ?
N2 C7 C10 122.0(2) . . ?
C8 C7 C10 128.3(2) . . ?
C9 C8 C7 106.8(2) . . ?
C9 C8 H8 126.6 . . ?
C7 C8 H8 126.6 . . ?
N1 C9 C8 106.1(2) . . ?
N1 C9 C11 122.9(2) . . ?
C8 C9 C11 131.0(3) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 N1 110.4(2) . . ?
N3 C12 H12A 109.6 . . ?
N1 C12 H12A 109.6 . . ?
N3 C12 H12B 109.6 . . ?
N1 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C15 N3 N4 111.1(2) . . ?
C15 N3 C12 130.6(2) . . ?
N4 N3 C12 117.9(2) . . ?
C13 N4 N3 106.0(2) . . ?
C13 N4 Pd 135.31(18) . . ?
N3 N4 Pd 117.54(16) . . ?
N4 C13 C14 109.8(2) . . ?
N4 C13 C16 121.6(2) . . ?
C14 C13 C16 128.6(2) . . ?
C15 C14 C13 106.7(2) . . ?
C15 C14 H14 126.6 . . ?
C13 C14 H14 126.6 . . ?
N3 C15 C14 106.3(2) . . ?
N3 C15 C17 122.6(2) . . ?
C14 C15 C17 131.1(2) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 27.15
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.736
_refine_diff_density_min -0.705
_refine_diff_density_rms 0.097
#===END