#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:09:12 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178837 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/91/4109192.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_4109192
loop_
_publ_author_name
'Qingwei Yao'
'Mark Zabawa'
'Joyce Woo'
'Chong Zheng'
_publ_section_title
;
 Carbocyclic Carbene Ligands Derived from Aromatic Nitrones: Formation and
 Catalytic Activity of Their Pd(II) Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3088
_journal_page_last               3089
_journal_paper_doi               10.1021/ja0701659
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C36 H48 N2 O10 Pd2'
_chemical_formula_weight         881.56
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 103.380(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1473(12)
_cell_length_b                   14.4545(14)
_cell_length_c                   20.3119(19)
_cell_measurement_reflns_used    503
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      -14
_cell_volume                     3755.3(6)
_computing_cell_refinement       'SMART and SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      203(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens SMART CCD  PLATFORM'
_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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13849
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.015
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.673914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2000)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.413
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.413
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0104P)²+7.3645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0632
_reflns_number_gt                3256
_reflns_number_total             3311
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0701659si20070109_035347.cif
_cod_data_source_block           yao29
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4109192
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Pd Pd 0.392969(17) 0.193591(15) 0.264120(11) 0.02915(8) Uani 1 1 d .
C1 C 0.3849(2) 0.2892(2) 0.33029(14) 0.0296(6) Uani 1 1 d .
C2 C 0.3873(2) 0.2667(2) 0.39769(14) 0.0323(6) Uani 1 1 d .
H2 H 0.3911 0.2044 0.4113 0.039 Uiso 1 1 calc R
C3 C 0.3839(2) 0.3357(2) 0.44419(15) 0.0336(7) Uani 1 1 d .
C4 C 0.3817(2) 0.4288(2) 0.42610(15) 0.0350(7) Uani 1 1 d .
H4 H 0.3817 0.4751 0.4586 0.042 Uiso 1 1 calc R
C5 C 0.3794(2) 0.4522(2) 0.36034(15) 0.0329(7) Uani 1 1 d .
C6 C 0.3767(2) 0.3825(2) 0.31043(14) 0.0293(6) Uani 1 1 d .
C7 C 0.3554(2) 0.4144(2) 0.24168(14) 0.0324(6) Uani 1 1 d .
H7 H 0.3629 0.4782 0.2353 0.039 Uiso 1 1 calc R
N8 N 0.32701(19) 0.36478(16) 0.18759(12) 0.0314(5) Uani 1 1 d .
O9 O 0.31909(17) 0.27295(14) 0.18786(10) 0.0374(5) Uani 1 1 d .
O11 O 0.45805(17) 0.10395(14) 0.33952(10) 0.0377(5) Uani 1 1 d .
C12 C 0.5504(2) 0.0732(2) 0.34761(15) 0.0339(7) Uani 1 1 d .
O12 O 0.38675(16) 0.08968(14) 0.18814(11) 0.0386(5) Uani 1 1 d .
C13 C 0.5857(3) 0.0082(3) 0.40677(17) 0.0494(9) Uani 1 1 d .
H13A H 0.5453 0.0197 0.4403 0.074 Uiso 1 1 calc R
H13B H 0.6593 0.0183 0.4269 0.074 Uiso 1 1 calc R
H13C H 0.5752 -0.0553 0.3911 0.074 Uiso 1 1 calc R
C21 C 0.0000 0.3728(4) 0.2500 0.0581(15) Uani 1 2 d S
H21 H 0.0000 0.4379 0.2500 0.070 Uiso 1 2 calc SR
C22 C 0.0923(3) 0.3252(3) 0.26881(18) 0.0547(10) Uani 1 1 d .
H22 H 0.1558 0.3575 0.2821 0.066 Uiso 1 1 calc R
C23 C 0.0918(3) 0.2310(3) 0.2682(2) 0.0578(10) Uani 1 1 d .
H23 H 0.1551 0.1982 0.2805 0.069 Uiso 1 1 calc R
C24 C 0.0000 0.1845(4) 0.2500 0.0614(15) Uani 1 2 d S
H24 H 0.0000 0.1195 0.2500 0.074 Uiso 1 2 calc SR
O31 O 0.38440(19) 0.32059(15) 0.51070(10) 0.0437(5) Uani 1 1 d .
C32 C 0.3923(3) 0.2275(3) 0.53437(17) 0.0518(9) Uani 1 1 d .
H32A H 0.3332 0.1922 0.5093 0.078 Uiso 1 1 calc R
H32B H 0.3925 0.2266 0.5821 0.078 Uiso 1 1 calc R
H32C H 0.4567 0.2004 0.5277 0.078 Uiso 1 1 calc R
O51 O 0.37895(19) 0.54076(14) 0.33762(11) 0.0427(5) Uani 1 1 d .
C52 C 0.3695(3) 0.6141(2) 0.38288(17) 0.0471(8) Uani 1 1 d .
H52A H 0.3052 0.6066 0.3980 0.071 Uiso 1 1 calc R
H52B H 0.3682 0.6729 0.3597 0.071 Uiso 1 1 calc R
H52C H 0.4286 0.6126 0.4216 0.071 Uiso 1 1 calc R
C81 C 0.2863(2) 0.4035(2) 0.11751(15) 0.0370(7) Uani 1 1 d .
C82 C 0.3394(3) 0.3517(3) 0.06994(17) 0.0554(10) Uani 1 1 d .
H82A H 0.4143 0.3621 0.0833 0.083 Uiso 1 1 calc R
H82B H 0.3129 0.3738 0.0241 0.083 Uiso 1 1 calc R
H82C H 0.3251 0.2861 0.0720 0.083 Uiso 1 1 calc R
C83 C 0.1701(3) 0.3869(3) 0.10082(19) 0.0628(12) Uani 1 1 d .
H83A H 0.1566 0.3209 0.0995 0.094 Uiso 1 1 calc R
H83B H 0.1390 0.4138 0.0571 0.094 Uiso 1 1 calc R
H83C H 0.1399 0.4153 0.1352 0.094 Uiso 1 1 calc R
C84 C 0.3092(4) 0.5066(3) 0.11572(19) 0.0682(12) Uani 1 1 d .
H84A H 0.2723 0.5393 0.1448 0.102 Uiso 1 1 calc R
H84B H 0.2862 0.5292 0.0697 0.102 Uiso 1 1 calc R
H84C H 0.3838 0.5169 0.1315 0.102 Uiso 1 1 calc R
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'
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'
H H 0.0000 0.0000 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 Pd O9 91.92(10) . .
C1 Pd O11 90.74(10) . .
O9 Pd O11 174.86(9) . .
C1 Pd O12 174.79(10) . .
O9 Pd O12 85.01(8) . .
O11 Pd O12 92.01(8) . .
C1 Pd Pd 109.58(8) . 2_655
O9 Pd Pd 99.30(7) . 2_655
O11 Pd Pd 83.94(6) . 2_655
O12 Pd Pd 75.12(6) . 2_655
C2 C1 C6 119.1(3) . .
C2 C1 Pd 121.2(2) . .
C6 C1 Pd 119.7(2) . .
C3 C2 C1 120.2(3) . .
O31 C3 C2 124.5(3) . .
O31 C3 C4 114.2(3) . .
C2 C3 C4 121.3(3) . .
C5 C4 C3 119.3(3) . .
O51 C5 C4 124.1(3) . .
O51 C5 C6 115.3(3) . .
C4 C5 C6 120.7(3) . .
C1 C6 C5 119.2(3) . .
C1 C6 C7 124.9(3) . .
C5 C6 C7 115.6(3) . .
N8 C7 C6 127.0(3) . .
C7 N8 O9 123.9(2) . .
C7 N8 C81 124.5(3) . .
O9 N8 C81 111.3(2) . .
N8 O9 Pd 123.58(17) . .
C12 O11 Pd 122.92(19) . .
O12 C12 O11 127.1(3) 2_655 .
O12 C12 C13 117.4(3) 2_655 .
O11 C12 C13 115.5(3) . .
C12 O12 Pd 129.5(2) 2_655 .
C22 C21 C22 119.7(5) 2 .
C23 C22 C21 119.8(4) . .
C24 C23 C22 120.0(4) . .
C23 C24 C23 120.6(5) . 2
C3 O31 C32 117.9(2) . .
C5 O51 C52 118.3(2) . .
C83 C81 N8 105.9(2) . .
C83 C81 C82 111.8(3) . .
N8 C81 C82 107.7(3) . .
C83 C81 C84 110.3(3) . .
N8 C81 C84 110.9(3) . .
C82 C81 C84 110.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd C1 1.948(3) .
Pd O9 1.991(2) .
Pd O11 2.037(2) .
Pd O12 2.142(2) .
Pd Pd 2.9995(5) 2_655
C1 C2 1.400(4) .
C1 C6 1.405(4) .
C2 C3 1.382(4) .
C3 O31 1.367(3) .
C3 C4 1.393(4) .
C4 C5 1.372(4) .
C5 O51 1.360(3) .
C5 C6 1.424(4) .
C6 C7 1.435(4) .
C7 N8 1.293(4) .
N8 O9 1.331(3) .
N8 C81 1.508(4) .
O11 C12 1.267(4) .
C12 O12 1.243(4) 2_655
C12 C13 1.512(4) .
O12 C12 1.243(4) 2_655
C21 C22 1.371(5) 2
C21 C22 1.371(5) .
C22 C23 1.362(6) .
C23 C24 1.356(5) .
C24 C23 1.356(5) 2
O31 C32 1.425(4) .
O51 C52 1.428(4) .
C81 C83 1.505(5) .
C81 C82 1.514(5) .
C81 C84 1.522(5) .
