#------------------------------------------------------------------------------
#$Date: 2016-06-18 11:01:35 +0200 (Sat 18 de Jun de 2016) $
#$Revision: 183735 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/54/7055438.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_7055438
loop_
_publ_author_name
'Steeples, Elliot'
'Kelling, Alexandra'
'Schilde, Uwe'
'Esposito, Davide'
_publ_section_title
;
 Amino acid-derived N-heterocyclic carbene palladium complexes for aqueous
 phase Suzuki--Miyaura couplings
;
_journal_issue                   6
_journal_name_full               'New J. Chem.'
_journal_page_first              4922
_journal_paper_doi               10.1039/C5NJ03337C
_journal_volume                  40
_journal_year                    2016
_chemical_formula_moiety         'C26 H40 Cl2 N4 O8 Pd'
_chemical_formula_sum            'C26 H40 Cl2 N4 O8 Pd'
_chemical_formula_weight         713.92
_chemical_name_systematic
'trans-dichlorido-bis(1,3-bis(2-ethoxy-2-oxopropyl)-imidazol-2-ylidine)- palladium(II)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-11-24 deposited with the CCDC.
2016-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.377(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3920(5)
_cell_length_b                   12.0677(7)
_cell_length_c                   25.5618(10)
_cell_measurement_reflns_used    12583
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      1.61
_cell_volume                     3171.4(3)
_computing_cell_refinement       'X-AREA (Stoe, 2011)'
_computing_data_collection       'X-AREA (Stoe, 2011)'
_computing_data_reduction        'X-RED (Stoe, 2009)'
_computing_molecular_graphics    'Diamond (Blankenburg, 2015)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      210(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
; 
 180 frames, 1 min exposure time
;
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'ω scan, δ ω = 1.0 deg'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10088
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.603
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  0.8510
_exptl_absorpt_correction_T_min  0.7458
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-RED (Stoe, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0052(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0234
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0308P)²+5.4133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0610
_reflns_number_gt                2648
_reflns_number_total             2804
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5nj03337c2.cif
_cod_data_source_block           4b
_cod_depositor_comments
'Adding full bibliography for 7055437--7055440.cif.'
_cod_database_code               7055438
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.0000 0.7812(2) -0.2500 0.0236(5) Uani 1 2 d S T P
C2 C -0.0131(2) 0.95921(18) -0.22517(10) 0.0357(5) Uani 1 1 d . . .
H2 H -0.025(2) 1.017(2) -0.2017(10) 0.043 Uiso 1 1 d . U .
C3 C -0.0524(2) 0.81372(19) -0.15912(8) 0.0309(5) Uani 1 1 d . . .
H3A H -0.0216 0.8692 -0.1322 0.037 Uiso 1 1 calc R U .
H3B H -0.0077 0.7438 -0.1490 0.037 Uiso 1 1 calc R U .
C4 C -0.1973(2) 0.7979(2) -0.16105(9) 0.0383(5) Uani 1 1 d . . .
H4A H -0.2428 0.8648 -0.1755 0.046 Uiso 1 1 calc R U .
H4B H -0.2262 0.7359 -0.1846 0.046 Uiso 1 1 calc R U .
C5 C -0.2320(2) 0.7749(2) -0.10716(9) 0.0406(6) Uani 1 1 d . . .
C6 C -0.3901(3) 0.7045(3) -0.05838(10) 0.0533(7) Uani 1 1 d . . .
H6A H -0.4093 0.7731 -0.0405 0.064 Uiso 1 1 calc R U .
H6B H -0.3218 0.6644 -0.0355 0.064 Uiso 1 1 calc R U .
C7 C -0.5095(4) 0.6348(3) -0.06935(15) 0.0778(11) Uani 1 1 d . . .
H7A H -0.5767 0.6754 -0.0918 0.117 Uiso 1 1 calc R U .
H7B H -0.5399 0.6163 -0.0363 0.117 Uiso 1 1 calc R U .
H7C H -0.4896 0.5672 -0.0871 0.117 Uiso 1 1 calc R U .
C8 C 0.0000 0.4455(2) -0.2500 0.0263(6) Uani 1 2 d S T P
C9 C -0.0458(2) 0.26779(18) -0.23425(9) 0.0343(5) Uani 1 1 d . . .
H9 H -0.088(3) 0.212(2) -0.2209(10) 0.041 Uiso 1 1 d . U .
C10 C -0.1641(2) 0.41329(19) -0.18977(9) 0.0327(5) Uani 1 1 d . . .
H10A H -0.2322 0.3574 -0.1892 0.039 Uiso 1 1 calc R U .
H10B H -0.2057 0.4829 -0.2028 0.039 Uiso 1 1 calc R U .
C11 C -0.0928(3) 0.4299(3) -0.13446(10) 0.0561(7) Uani 1 1 d . . .
H11A H -0.0334 0.3675 -0.1255 0.067 Uiso 1 1 calc R U .
H11B H -0.0402 0.4975 -0.1338 0.067 Uiso 1 1 calc R U .
C12 C -0.1806(2) 0.4391(2) -0.09361(10) 0.0415(6) Uani 1 1 d . . .
C13 C -0.1881(3) 0.4439(3) -0.00096(12) 0.0688(9) Uani 1 1 d . . .
H13A H -0.1795 0.5200 0.0125 0.083 Uiso 1 1 calc R U .
H13B H -0.2808 0.4278 -0.0113 0.083 Uiso 1 1 calc R U .
C14 C -0.1318(4) 0.3665(3) 0.03967(13) 0.0755(10) Uani 1 1 d . . .
H14A H -0.1481 0.2912 0.0272 0.113 Uiso 1 1 calc R U .
H14B H -0.1709 0.3778 0.0715 0.113 Uiso 1 1 calc R U .
H14C H -0.0387 0.3789 0.0475 0.113 Uiso 1 1 calc R U .
Cl1 Cl 0.18878(5) 0.61019(4) -0.18966(2) 0.03433(14) Uani 1 1 d . . .
N1 N -0.02046(16) 0.84978(14) -0.21023(7) 0.0263(4) Uani 1 1 d . . .
N2 N -0.07392(17) 0.37742(14) -0.22519(7) 0.0288(4) Uani 1 1 d . . .
O1 O -0.1649(2) 0.7989(3) -0.06721(8) 0.1073(12) Uani 1 1 d . . .
O2 O -0.34731(18) 0.72985(19) -0.10890(6) 0.0542(5) Uani 1 1 d . . .
O3 O -0.2916(2) 0.4538(4) -0.10335(10) 0.1234(14) Uani 1 1 d . . .
O4 O -0.1195(2) 0.4319(3) -0.04595(8) 0.0849(8) Uani 1 1 d . . .
Pd1 Pd 0.0000 0.61302(2) -0.2500 0.02123(10) Uani 1 2 d S T P
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N1 104.5(2) 6 . y
N1 C1 Pd1 127.77(12) 6 . y
N1 C1 Pd1 127.77(12) . . y
C2 C2 N1 106.86(12) 6 . y
C2 C2 H2 132.1(16) 6 . n
N1 C2 H2 121.0(16) . . n
N1 C3 C4 111.33(17) . . y
N1 C3 H3A 109.4 . . n
C4 C3 H3A 109.4 . . n
N1 C3 H3B 109.4 . . n
C4 C3 H3B 109.4 . . n
H3A C3 H3B 108.0 . . n
C5 C4 C3 111.43(18) . . y
C5 C4 H4A 109.3 . . n
C3 C4 H4A 109.3 . . n
C5 C4 H4B 109.3 . . n
C3 C4 H4B 109.3 . . n
H4A C4 H4B 108.0 . . n
O1 C5 O2 123.4(2) . . y
O1 C5 C4 123.8(2) . . y
O2 C5 C4 112.7(2) . . y
O2 C6 C7 107.8(2) . . n
O2 C6 H6A 110.2 . . n
C7 C6 H6A 110.2 . . n
O2 C6 H6B 110.2 . . n
C7 C6 H6B 110.2 . . n
H6A C6 H6B 108.5 . . n
C6 C7 H7A 109.5 . . n
C6 C7 H7B 109.5 . . n
H7A C7 H7B 109.5 . . n
C6 C7 H7C 109.5 . . n
H7A C7 H7C 109.5 . . n
H7B C7 H7C 109.5 . . n
N2 C8 N2 104.7(2) . 6 y
N2 C8 Pd1 127.66(12) . . y
N2 C8 Pd1 127.66(12) 6 . y
C9 C9 N2 106.77(13) 6 . y
C9 C9 H9 131.6(17) 6 . n
N2 C9 H9 121.6(17) . . n
N2 C10 C11 110.40(19) . . y
N2 C10 H10A 109.6 . . n
C11 C10 H10A 109.6 . . n
N2 C10 H10B 109.6 . . n
C11 C10 H10B 109.6 . . n
H10A C10 H10B 108.1 . . n
C12 C11 C10 113.6(2) . . y
C12 C11 H11A 108.9 . . n
C10 C11 H11A 108.9 . . n
C12 C11 H11B 108.9 . . n
C10 C11 H11B 108.9 . . n
H11A C11 H11B 107.7 . . n
O3 C12 O4 123.4(3) . . y
O3 C12 C11 123.7(3) . . y
O4 C12 C11 112.9(2) . . y
C14 C13 O4 108.0(3) . . n
C14 C13 H13A 110.1 . . n
O4 C13 H13A 110.1 . . n
C14 C13 H13B 110.1 . . n
O4 C13 H13B 110.1 . . n
H13A C13 H13B 108.4 . . n
C13 C14 H14A 109.5 . . n
C13 C14 H14B 109.5 . . n
H14A C14 H14B 109.5 . . n
C13 C14 H14C 109.5 . . n
H14A C14 H14C 109.5 . . n
H14B C14 H14C 109.5 . . n
C1 N1 C2 110.91(18) . . y
C1 N1 C3 124.86(18) . . y
C2 N1 C3 124.17(18) . . y
C8 N2 C9 110.89(19) . . y
C8 N2 C10 124.97(18) . . y
C9 N2 C10 123.95(18) . . y
C5 O2 C6 116.9(2) . . y
C12 O4 C13 120.8(2) . . y
C8 Pd1 C1 180.0 . . y
C8 Pd1 Cl1 89.155(14) . . y
C1 Pd1 Cl1 90.845(14) . . y
C8 Pd1 Cl1 89.154(14) . 6 y
C1 Pd1 Cl1 90.846(14) . 6 y
Cl1 Pd1 Cl1 178.31(3) . 6 y
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
C1 N1 1.352(2) 6 y
C1 N1 1.352(2) . y
C1 Pd1 2.029(3) . y
C2 C2 1.336(5) 6 y
C2 N1 1.380(3) . y
C2 H2 0.93(3) . n
C3 N1 1.461(3) . y
C3 C4 1.511(3) . y
C3 H3A 0.9800 . n
C3 H3B 0.9800 . n
C4 C5 1.500(3) . y
C4 H4A 0.9800 . n
C4 H4B 0.9800 . n
C5 O1 1.186(3) . y
C5 O2 1.311(3) . y
C6 O2 1.458(3) . y
C6 C7 1.492(4) . y
C6 H6A 0.9800 . n
C6 H6B 0.9800 . n
C7 H7A 0.9700 . n
C7 H7B 0.9700 . n
C7 H7C 0.9700 . n
C8 N2 1.345(2) . y
C8 N2 1.345(2) 6 y
C8 Pd1 2.021(3) . y
C9 C9 1.333(5) 6 y
C9 N2 1.382(3) . y
C9 H9 0.90(3) . n
C10 N2 1.460(3) . y
C10 C11 1.511(3) . y
C10 H10A 0.9800 . n
C10 H10B 0.9800 . n
C11 C12 1.488(3) . y
C11 H11A 0.9800 . n
C11 H11B 0.9800 . n
C12 O3 1.158(3) . y
C12 O4 1.292(3) . y
C13 C14 1.455(5) . y
C13 O4 1.446(3) . y
C13 H13A 0.9800 . n
C13 H13B 0.9800 . n
C14 H14A 0.9700 . n
C14 H14B 0.9700 . n
C14 H14C 0.9700 . n
Cl1 Pd1 2.3124(5) . y
Pd1 Cl1 2.3124(5) 6 y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_publ_flag
N1 C3 C4 C5 -172.8(2) . y
C3 C4 C5 O1 21.4(4) . y
C3 C4 C5 O2 -161.4(2) . y
N2 C10 C11 C12 -165.7(2) . y
C10 C11 C12 O3 -14.2(5) . y
C10 C11 C12 O4 167.4(3) . y
N1 C1 N1 C2 0.13(12) 6 y
Pd1 C1 N1 C2 -179.87(12) . y
N1 C1 N1 C3 177.4(2) 6 y
Pd1 C1 N1 C3 -2.7(2) . y
C2 C2 N1 C1 -0.4(3) 6 y
C2 C2 N1 C3 -177.6(2) 6 y
C4 C3 N1 C1 -86.6(2) . y
C4 C3 N1 C2 90.2(3) . y
N2 C8 N2 C9 0.32(11) 6 y
Pd1 C8 N2 C9 -179.68(11) . y
N2 C8 N2 C10 175.5(2) 6 y
Pd1 C8 N2 C10 -4.5(2) . y
C9 C9 N2 C8 -0.8(3) 6 y
C9 C9 N2 C10 -176.1(2) 6 y
C11 C10 N2 C8 -84.4(2) . y
C11 C10 N2 C9 90.2(3) . y
O1 C5 O2 C6 -2.7(5) . y
C4 C5 O2 C6 -179.9(2) . y
C7 C6 O2 C5 -169.1(3) . y
O3 C12 O4 C13 -1.1(6) . y
C11 C12 O4 C13 177.2(3) . y
C14 C13 O4 C12 142.7(3) . y
