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#$Date: 2016-03-21 07:47:51 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178582 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/93/4069341.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4069341
loop_
_publ_author_name
'Bortoluzzi, Marco'
'Paolucci, Gino'
'Pitteri, Bruno'
'Vavasori, Andrea'
'Bertolasi, Valerio'
_publ_section_title
;
 Synthesis and Reactivity of Mixed-Ligand Palladium(II) Organometallic
 Complexes with Phosphites and Bis(pyrazol-1-yl)methane
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              3247
_journal_paper_doi               10.1021/om900146a
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C14 H26 N4 O3 P Pd, Cl O4'
_chemical_formula_sum            'C14 H26 Cl N4 O7 P Pd'
_chemical_formula_weight         535.21
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.5022(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6637(2)
_cell_length_b                   9.5738(2)
_cell_length_c                   19.8507(4)
_cell_measurement_reflns_used    15228
_cell_measurement_temperature    295
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      3.52
_cell_volume                     2202.39(7)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
'SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.; 1999)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18140
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    1.077
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'SORTAV (R.H. Blessing, Acta Crystallogr., 1995, A51, 33)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.944
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0685P)²+0.1402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1115
_reflns_number_gt                4044
_reflns_number_total             5301
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            om900146a_si_002.cif
_cod_data_source_block           (3Et)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4069341
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'
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
Pd1 Pd 0.314417(18) 0.20117(2) 0.074193(11) 0.03947(11) Uani 1 1 d .
N1 N 0.3725(2) 0.1824(2) 0.17863(13) 0.0436(6) Uani 1 1 d .
N2 N 0.3604(2) 0.0615(2) 0.21266(12) 0.0436(6) Uani 1 1 d .
N3 N 0.3439(2) -0.0219(2) 0.06649(12) 0.0428(6) Uani 1 1 d .
N4 N 0.3402(2) -0.1031(3) 0.12229(13) 0.0446(6) Uani 1 1 d .
C1 C 0.2878(4) 0.4089(4) 0.0886(2) 0.0731(11) Uani 1 1 d .
H1A H 0.2864 0.4269 0.1360 0.088 Uiso 1 1 calc R
H1B H 0.2154 0.4360 0.0642 0.088 Uiso 1 1 calc R
H1C H 0.3491 0.4614 0.0722 0.088 Uiso 1 1 calc R
C2 C 0.4343(3) 0.2656(4) 0.22336(18) 0.0526(8) Uani 1 1 d .
C3 C 0.4608(3) 0.1988(4) 0.2843(2) 0.0610(9) Uani 1 1 d .
C4 C 0.4131(3) 0.0700(4) 0.27663(17) 0.0544(8) Uani 1 1 d .
C5 C 0.2903(3) -0.0486(3) 0.18026(18) 0.0502(7) Uani 1 1 d .
C6 C 0.3881(3) -0.1025(3) 0.02239(18) 0.0495(7) Uani 1 1 d .
C7 C 0.4131(4) -0.2343(4) 0.0494(2) 0.0576(9) Uani 1 1 d .
C8 C 0.3820(3) -0.2309(3) 0.1119(2) 0.0544(9) Uani 1 1 d .
P1 P 0.25548(7) 0.24706(9) -0.03264(4) 0.04331(19) Uani 1 1 d .
O1 O 0.12213(19) 0.2715(2) -0.05092(12) 0.0550(6) Uani 1 1 d .
O2 O 0.30658(19) 0.3823(2) -0.06262(12) 0.0604(6) Uani 1 1 d .
O3 O 0.2896(2) 0.1234(2) -0.07885(11) 0.0568(6) Uani 1 1 d .
C9 C 0.0395(3) 0.1888(5) -0.0186(2) 0.0745(12) Uani 1 1 d .
H9A H 0.0297 0.0988 -0.0409 0.089 Uiso 1 1 calc R
H9B H 0.0689 0.1727 0.0284 0.089 Uiso 1 1 calc R
C10 C -0.0705(4) 0.2581(7) -0.0218(3) 0.1141(19) Uani 1 1 d .
H10A H -0.0642 0.3380 0.0076 0.171 Uiso 1 1 calc R
H10B H -0.1270 0.1948 -0.0077 0.171 Uiso 1 1 calc R
H10C H -0.0938 0.2878 -0.0675 0.171 Uiso 1 1 calc R
C11 C 0.2766(4) 0.1229(5) -0.15245(19) 0.0775(12) Uani 1 1 d .
H11A H 0.3088 0.2079 -0.1691 0.093 Uiso 1 1 calc R
H11B H 0.1954 0.1190 -0.1696 0.093 Uiso 1 1 calc R
C12 C 0.3361(4) 0.0021(5) -0.1760(2) 0.0887(14) Uani 1 1 d .
H12A H 0.4162 0.0060 -0.1584 0.133 Uiso 1 1 calc R
H12B H 0.3292 0.0022 -0.2246 0.133 Uiso 1 1 calc R
H12C H 0.3024 -0.0817 -0.1604 0.133 Uiso 1 1 calc R
C13 C 0.2474(4) 0.4835(5) -0.1077(3) 0.0960(16) Uani 1 1 d .
H13A H 0.2060 0.4360 -0.1461 0.115 Uiso 1 1 calc R
H13B H 0.1916 0.5336 -0.0841 0.115 Uiso 1 1 calc R
C14 C 0.3276(4) 0.5808(5) -0.1311(3) 0.1040(17) Uani 1 1 d .
H14A H 0.3763 0.6179 -0.0931 0.156 Uiso 1 1 calc R
H14B H 0.2860 0.6557 -0.1550 0.156 Uiso 1 1 calc R
H14C H 0.3742 0.5340 -0.1610 0.156 Uiso 1 1 calc R
Cl1 Cl 0.00372(8) 0.16057(9) 0.19581(5) 0.0587(2) Uani 1 1 d .
O4 O 0.0016(4) 0.0474(4) 0.1499(2) 0.1245(14) Uani 1 1 d .
O5 O -0.0565(5) 0.1301(9) 0.2484(3) 0.213(3) Uani 1 1 d .
O6 O 0.1151(3) 0.1942(5) 0.2200(3) 0.171(3) Uani 1 1 d .
O7 O -0.0504(7) 0.2710(5) 0.1677(4) 0.238(4) Uani 1 1 d .
H2 H 0.448(3) 0.348(5) 0.214(2) 0.082(14) Uiso 1 1 d .
H3 H 0.499(3) 0.238(4) 0.322(2) 0.066(11) Uiso 1 1 d .
H4 H 0.412(3) -0.012(4) 0.3024(18) 0.058(10) Uiso 1 1 d .
H5A H 0.291(3) -0.116(4) 0.2150(19) 0.058(10) Uiso 1 1 d .
H5B H 0.218(3) 0.001(4) 0.1644(17) 0.051(9) Uiso 1 1 d .
H6 H 0.394(3) -0.065(4) -0.0190(19) 0.054(10) Uiso 1 1 d .
H7 H 0.453(3) -0.292(4) 0.037(2) 0.053(11) Uiso 1 1 d .
H8 H 0.387(3) -0.286(3) 0.1499(19) 0.050(10) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
P P 0.1023 0.0942 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 Pd1 N1 89.01(13)
C1 Pd1 N3 176.01(13)
N1 Pd1 N3 87.12(9)
C1 Pd1 P1 84.50(12)
N1 Pd1 P1 173.34(6)
N3 Pd1 P1 99.40(7)
C2 N1 N2 104.8(3)
C2 N1 Pd1 133.4(2)
N2 N1 Pd1 121.42(18)
C4 N2 N1 110.8(3)
C4 N2 C5 129.8(3)
N1 N2 C5 119.2(2)
C6 N3 N4 105.0(3)
C6 N3 Pd1 134.5(2)
N4 N3 Pd1 119.03(18)
C8 N4 N3 110.6(3)
C8 N4 C5 129.6(3)
N3 N4 C5 119.8(2)
Pd1 C1 H1A 109.5
Pd1 C1 H1B 109.5
H1A C1 H1B 109.5
Pd1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 C3 111.0(3)
N1 C2 H2 121(3)
C3 C2 H2 128(3)
C4 C3 C2 106.0(3)
C4 C3 H3 129(3)
C2 C3 H3 125(3)
N2 C4 C3 107.4(3)
N2 C4 H4 115(2)
C3 C4 H4 137(2)
N2 C5 N4 111.1(3)
N2 C5 H5A 102(2)
N4 C5 H5A 111(2)
N2 C5 H5B 102.2(19)
N4 C5 H5B 109.1(19)
H5A C5 H5B 120(3)
N3 C6 C7 110.9(3)
N3 C6 H6 117(2)
C7 C6 H6 132(2)
C8 C7 C6 105.6(3)
C8 C7 H7 123(3)
C6 C7 H7 129(3)
C7 C8 N4 107.9(3)
C7 C8 H8 139(2)
N4 C8 H8 113(2)
O2 P1 O1 101.39(13)
O2 P1 O3 105.49(13)
O1 P1 O3 106.59(14)
O2 P1 Pd1 116.08(10)
O1 P1 Pd1 116.42(10)
O3 P1 Pd1 109.85(9)
C9 O1 P1 120.3(2)
C13 O2 P1 127.9(2)
C11 O3 P1 125.7(2)
C10 C9 O1 111.2(4)
C10 C9 H9A 109.4
O1 C9 H9A 109.4
C10 C9 H9B 109.4
O1 C9 H9B 109.4
H9A C9 H9B 108.0
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O3 C11 C12 109.1(3)
O3 C11 H11A 109.9
C12 C11 H11A 109.9
O3 C11 H11B 109.9
C12 C11 H11B 109.9
H11A C11 H11B 108.3
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C14 C13 O2 110.7(4)
C14 C13 H13A 109.5
O2 C13 H13A 109.5
C14 C13 H13B 109.5
O2 C13 H13B 109.5
H13A C13 H13B 108.1
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O7 Cl1 O5 103.5(5)
O7 Cl1 O6 110.4(4)
O5 Cl1 O6 109.5(4)
O7 Cl1 O4 111.6(4)
O5 Cl1 O4 111.0(4)
O6 Cl1 O4 110.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C1 2.038(3)
Pd1 N1 2.115(3)
Pd1 N3 2.171(2)
Pd1 P1 2.1984(8)
N1 C2 1.341(4)
N1 N2 1.356(3)
N2 C4 1.349(4)
N2 C5 1.440(4)
N3 C6 1.315(4)
N3 N4 1.358(3)
N4 C8 1.342(4)
N4 C5 1.444(4)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.373(5)
C2 H2 0.83(5)
C3 C4 1.355(5)
C3 H3 0.91(4)
C4 H4 0.94(4)
C5 H5A 0.94(4)
C5 H5B 0.99(3)
C6 C7 1.389(5)
C6 H6 0.91(4)
C7 C8 1.333(5)
C7 H7 0.78(4)
C8 H8 0.92(4)
P1 O2 1.570(2)
P1 O1 1.574(2)
P1 O3 1.576(2)
O1 C9 1.452(4)
O2 C13 1.441(4)
O3 C11 1.452(4)
C9 C10 1.440(6)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 C12 1.453(6)
C11 H11A 0.9700
C11 H11B 0.9700
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 C14 1.434(6)
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
Cl1 O7 1.322(5)
Cl1 O5 1.355(5)
Cl1 O6 1.372(4)
Cl1 O4 1.414(3)
