#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:16:28 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178892 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/21/4112123.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_4112123
loop_
_publ_author_name
'Adelina M. Voutchkova'
'Leah N. Appelhans'
'Anthony R. Chianese'
'Robert H. Crabtree'
_publ_contact_author
;
     Prof. Robert H. Crabtree
     Department of Chemistry
     Yale University
     225 Prospect St
     PO Box 208107
     New Haven, CT 06520-8107
     USA
;
_publ_contact_author_email       robert.crabtree@yale.edu
_publ_contact_author_fax         '+203 432 6144'
_publ_contact_author_phone       '+203 432 3925'
_publ_section_title
;
 Disubstituted Imidazolium-2-Carboxylates as Efficient Precursors to
 N-Heterocyclic Carbene Complexes of Rh, Ru, Ir, and Pd
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17624
_journal_page_last               17625
_journal_paper_doi               10.1021/ja056625k
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C19 H36 N6 O7 Pd'
_chemical_formula_weight         566.94
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 97.58(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.831(2)
_cell_length_b                   14.289(3)
_cell_length_c                   18.686(4)
_cell_measurement_temperature    173(2)
_cell_volume                     2602.0(10)
_computing_cell_refinement       Denzo
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        Denzo
_computing_molecular_graphics    XP
_computing_publication_material  XCIF
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9765
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  0.9278
_exptl_absorpt_correction_T_min  0.9278
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.851
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         6408
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.104
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1296
_reflns_number_gt                4831
_reflns_number_total             6408
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja056625ksi20051004_082816.cif
_cod_data_source_block           av01
_cod_original_cell_volume        2602.0(9)
_cod_database_code               4112123
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'
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 0.56510(2) 0.458565(16) 0.831199(12) 0.02244(10) Uani 1 1 d .
O1 O 0.7514(2) 0.50743(18) 0.88584(12) 0.0294(5) Uani 1 1 d .
O2 O 0.7959(3) 0.57968(19) 0.78654(13) 0.0377(6) Uani 1 1 d .
O3 O 1.3733(3) 0.3518(3) 0.50873(19) 0.0713(10) Uani 1 1 d .
O4 O 1.2185(4) 0.4579(2) 0.5255(2) 0.0574(9) Uani 1 1 d .
N1 N 0.7671(3) 0.3118(2) 0.79082(16) 0.0321(7) Uani 1 1 d .
N2 N 0.6881(3) 0.3920(2) 0.69837(15) 0.0311(6) Uani 1 1 d .
N3 N 0.3457(3) 0.31663(19) 0.79087(15) 0.0289(6) Uani 1 1 d .
N4 N 0.2925(3) 0.44846(19) 0.74055(16) 0.0308(7) Uani 1 1 d .
N5 N 0.3653(3) 0.5176(2) 0.93705(14) 0.0256(6) Uani 1 1 d .
N6 N 0.4630(3) 0.63662(19) 0.89731(14) 0.0282(6) Uani 1 1 d .
C1 C 0.6767(3) 0.3798(2) 0.76921(18) 0.0269(7) Uani 1 1 d .
C2 C 0.8361(4) 0.2821(3) 0.7355(2) 0.0383(9) Uani 1 1 d .
H2A H 0.9050 0.2351 0.7379 0.046 Uiso 1 1 calc R
C3 C 0.7864(4) 0.3328(3) 0.6776(2) 0.0395(9) Uani 1 1 d .
H3A H 0.8138 0.3288 0.6308 0.047 Uiso 1 1 calc R
C4 C 0.8003(4) 0.2783(3) 0.8654(2) 0.0423(9) Uani 1 1 d .
H4A H 0.7388 0.3081 0.8959 0.063 Uiso 1 1 calc R
H4B H 0.8956 0.2943 0.8835 0.063 Uiso 1 1 calc R
H4C H 0.7885 0.2103 0.8667 0.063 Uiso 1 1 calc R
C5 C 0.6127(5) 0.4602(3) 0.6511(2) 0.0405(9) Uani 1 1 d .
H5B H 0.5604 0.4279 0.6101 0.061 Uiso 1 1 calc R
H5C H 0.6773 0.5040 0.6334 0.061 Uiso 1 1 calc R
H5A H 0.5496 0.4947 0.6779 0.061 Uiso 1 1 calc R
C6 C 0.3924(3) 0.4041(2) 0.78394(16) 0.0249(7) Uani 1 1 d .
C7 C 0.2157(4) 0.3069(3) 0.7520(2) 0.0416(9) Uani 1 1 d .
H7A H 0.1604 0.2522 0.7486 0.050 Uiso 1 1 calc R
C8 C 0.1834(4) 0.3892(3) 0.7204(2) 0.0410(9) Uani 1 1 d .
H8A H 0.1011 0.4041 0.6899 0.049 Uiso 1 1 calc R
C9 C 0.4147(4) 0.2418(2) 0.8348(2) 0.0351(8) Uani 1 1 d .
H9A H 0.5050 0.2636 0.8570 0.053 Uiso 1 1 calc R
H9B H 0.4260 0.1874 0.8042 0.053 Uiso 1 1 calc R
H9C H 0.3594 0.2241 0.8726 0.053 Uiso 1 1 calc R
C10 C 0.2971(4) 0.5459(2) 0.7163(2) 0.0386(9) Uani 1 1 d .
H10A H 0.3842 0.5744 0.7370 0.058 Uiso 1 1 calc R
H10B H 0.2207 0.5808 0.7321 0.058 Uiso 1 1 calc R
H10C H 0.2897 0.5476 0.6634 0.058 Uiso 1 1 calc R
C11 C 0.4558(3) 0.5423(2) 0.89205(18) 0.0256(7) Uani 1 1 d .
C12 C 0.3188(3) 0.5953(3) 0.97065(18) 0.0304(8) Uani 1 1 d .
H12A H 0.2554 0.5956 1.0049 0.036 Uiso 1 1 calc R
C13 C 0.3795(4) 0.6697(3) 0.94597(18) 0.0332(8) Uani 1 1 d .
H13A H 0.3679 0.7331 0.9592 0.040 Uiso 1 1 calc R
C14 C 0.3189(4) 0.4225(3) 0.94981(18) 0.0310(8) Uani 1 1 d .
H14A H 0.3641 0.3783 0.9205 0.047 Uiso 1 1 calc R
H14B H 0.2193 0.4187 0.9365 0.047 Uiso 1 1 calc R
H14C H 0.3424 0.4068 1.0010 0.047 Uiso 1 1 calc R
C15 C 0.5421(4) 0.6965(3) 0.8558(2) 0.0386(9) Uani 1 1 d .
H15A H 0.5932 0.6580 0.8252 0.058 Uiso 1 1 calc R
H15B H 0.6065 0.7338 0.8888 0.058 Uiso 1 1 calc R
H15C H 0.4800 0.7384 0.8255 0.058 Uiso 1 1 calc R
C16 C 0.8308(4) 0.5506(2) 0.8482(2) 0.0310(8) Uani 1 1 d .
C17 C 0.9761(4) 0.5655(4) 0.8844(3) 0.0576(13) Uani 1 1 d .
H17A H 1.0287 0.5988 0.8514 0.086 Uiso 1 1 calc R
H17B H 1.0190 0.5047 0.8969 0.086 Uiso 1 1 calc R
H17C H 0.9746 0.6026 0.9284 0.086 Uiso 1 1 calc R
C18 C 1.2550(5) 0.3754(3) 0.5138(2) 0.0506(11) Uani 1 1 d .
C19 C 1.1460(6) 0.2997(3) 0.5048(3) 0.0779(17) Uani 1 1 d .
H19A H 1.1887 0.2394 0.4962 0.117 Uiso 1 1 calc R
H19B H 1.0771 0.3149 0.4637 0.117 Uiso 1 1 calc R
H19C H 1.1018 0.2957 0.5488 0.117 Uiso 1 1 calc R
O5 O 0.9624(3) 0.6211(2) 0.68520(17) 0.0551(8) Uani 1 1 d D
H5 H 0.887(3) 0.604(4) 0.714(2) 0.078(16) Uiso 1 1 d D
H5' H 0.969(5) 0.563(2) 0.656(2) 0.069(16) Uiso 1 1 d D
O6 O 0.9792(4) 0.4783(2) 0.58620(17) 0.0571(8) Uani 1 1 d D
H6 H 1.074(3) 0.471(4) 0.573(3) 0.11(2) Uiso 1 1 d D
H6' H 0.904(5) 0.495(5) 0.547(3) 0.12(2) Uiso 1 1 d D
O7 O 1.6230(4) 0.3800(3) 0.4618(2) 0.0737(10) Uani 1 1 d D
H7 H 1.536(3) 0.388(5) 0.484(3) 0.12(2) Uiso 1 1 d D
H7' H 1.693(6) 0.431(4) 0.471(4) 0.16(3) Uiso 1 1 d D
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 Pd1 C1 91.39(13)
C6 Pd1 C11 89.72(13)
C1 Pd1 C11 177.84(13)
C6 Pd1 O1 175.81(11)
C1 Pd1 O1 87.67(11)
C11 Pd1 O1 91.36(11)
C16 O1 Pd1 116.8(2)
C1 N1 C2 111.7(3)
C1 N1 C4 125.2(3)
C2 N1 C4 122.9(3)
C1 N2 C3 110.4(3)
C1 N2 C5 125.4(3)
C3 N2 C5 124.1(3)
C6 N3 C7 110.1(3)
C6 N3 C9 126.6(3)
C7 N3 C9 123.2(3)
C6 N4 C8 110.8(3)
C6 N4 C10 125.6(3)
C8 N4 C10 123.6(3)
C11 N5 C12 111.0(3)
C11 N5 C14 126.1(3)
C12 N5 C14 122.9(3)
C11 N6 C13 111.0(3)
C11 N6 C15 125.2(3)
C13 N6 C15 123.8(3)
N1 C1 N2 104.5(3)
N1 C1 Pd1 127.9(2)
N2 C1 Pd1 127.3(3)
C3 C2 N1 106.0(3)
C2 C3 N2 107.4(3)
N3 C6 N4 105.4(3)
N3 C6 Pd1 127.6(2)
N4 C6 Pd1 127.0(2)
C8 C7 N3 107.0(3)
C7 C8 N4 106.8(3)
N5 C11 N6 104.3(3)
N5 C11 Pd1 129.1(2)
N6 C11 Pd1 126.6(3)
C13 C12 N5 107.1(3)
C12 C13 N6 106.7(3)
O2 C16 O1 124.4(3)
O2 C16 C17 120.0(4)
O1 C16 C17 115.6(3)
O3 C18 O4 124.5(5)
O3 C18 C19 117.2(5)
O4 C18 C19 118.3(4)
H5 O5 H5' 102(4)
H6' O6 H6 117(5)
H7 O7 H7' 116(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C6 1.968(3)
Pd1 C1 2.036(3)
Pd1 C11 2.049(3)
Pd1 O1 2.096(2)
O1 C16 1.275(4)
O2 C16 1.231(4)
O3 C18 1.226(5)
O4 C18 1.259(5)
N1 C1 1.343(4)
N1 C2 1.376(5)
N1 C4 1.469(5)
N2 C1 1.354(4)
N2 C3 1.377(5)
N2 C5 1.451(5)
N3 C6 1.344(4)
N3 C7 1.391(5)
N3 C9 1.460(4)
N4 C6 1.347(4)
N4 C8 1.379(5)
N4 C10 1.467(4)
N5 C11 1.349(4)
N5 C12 1.383(4)
N5 C14 1.463(5)
N6 C11 1.353(4)
N6 C13 1.386(4)
N6 C15 1.448(5)
C2 C3 1.340(6)
C7 C8 1.335(5)
C12 C13 1.331(5)
C16 C17 1.513(5)
C18 C19 1.517(7)
O5 H5 1.0000(11)
O5 H5' 1.0000(10)
O6 H6' 1.0000(11)
O6 H6 1.0000(11)
O7 H7 1.0000(11)
O7 H7' 1.0001(13)
