#------------------------------------------------------------------------------
#$Date: 2016-06-18 12:01:35 +0300 (Sat, 18 Jun 2016) $
#$Revision: 183735 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/54/7055440.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_7055440
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         'C18 H25 Cl2 N3 O4 Pd'
_chemical_formula_sum            'C18 H25 Cl2 N3 O4 Pd'
_chemical_formula_weight         524.71
_chemical_name_systematic
'trans-dichlorido-(1,3-bis(2-ethoxy-2-oxopropyl)-imidazol-2-ylidine)- pyridine-palladium(II) chloroform solvate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_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                93.265(6)
_cell_angle_beta                 95.848(6)
_cell_angle_gamma                98.828(6)
_cell_formula_units_Z            2
_cell_length_a                   9.4985(8)
_cell_length_b                   9.7104(7)
_cell_length_c                   12.2951(10)
_cell_measurement_reflns_used    32871
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      29.65
_cell_measurement_theta_min      1.73
_cell_volume                     1111.72(15)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
; 
 360 frames, 0.7 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  0.0243
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14413
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.669
_exptl_absorpt_coefficient_mu    1.102
_exptl_absorpt_correction_T_max  0.9114
_exptl_absorpt_correction_T_min  0.7326
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-RED (Stoe, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0063(5)
_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   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0194
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0314P)²+0.3744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0525
_refine_ls_wR_factor_ref         0.0533
_reflns_number_gt                3670
_reflns_number_total             3924
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5nj03337c2.cif
_cod_data_source_block           5b
_cod_depositor_comments
'Adding full bibliography for 7055437--7055440.cif.'
_cod_database_code               7055440
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.28070(19) 0.58204(18) 0.40661(14) 0.0286(4) Uani 1 1 d . .
C2 C 0.3538(2) 0.62807(19) 0.58596(15) 0.0329(4) Uani 1 1 d . .
H2 H 0.3837 0.6150 0.6594 0.040 Uiso 1 1 calc R U
C3 C 0.3359(2) 0.74964(19) 0.54386(15) 0.0334(4) Uani 1 1 d . .
H3 H 0.3512 0.8381 0.5823 0.040 Uiso 1 1 calc R U
C4 C 0.3186(2) 0.37599(18) 0.51089(15) 0.0308(4) Uani 1 1 d . .
H4A H 0.4063 0.3625 0.5555 0.037 Uiso 1 1 calc R U
H4B H 0.3173 0.3285 0.4382 0.037 Uiso 1 1 calc R U
C5 C 0.1897(2) 0.31207(19) 0.56357(17) 0.0367(4) Uani 1 1 d . .
H5A H 0.1894 0.3614 0.6353 0.044 Uiso 1 1 calc R U
H5B H 0.1020 0.3230 0.5178 0.044 Uiso 1 1 calc R U
C6 C 0.1913(2) 0.15938(19) 0.57773(15) 0.0315(4) Uani 1 1 d . .
C7 C 0.0793(2) -0.0391(2) 0.65931(18) 0.0418(5) Uani 1 1 d . .
H7A H 0.1042 -0.0940 0.5968 0.050 Uiso 1 1 calc R U
H7B H -0.0182 -0.0780 0.6732 0.050 Uiso 1 1 calc R U
C8 C 0.1826(3) -0.0484(2) 0.75894(19) 0.0517(5) Uani 1 1 d . .
H8A H 0.1783 -0.1454 0.7754 0.078 Uiso 1 1 calc R U
H8B H 0.2791 -0.0110 0.7447 0.078 Uiso 1 1 calc R U
H8C H 0.1569 0.0050 0.8209 0.078 Uiso 1 1 calc R U
C9 C 0.2535(2) 0.82153(19) 0.35603(16) 0.0347(4) Uani 1 1 d . .
H9A H 0.1947 0.8826 0.3902 0.042 Uiso 1 1 calc R U
H9B H 0.1959 0.7715 0.2909 0.042 Uiso 1 1 calc R U
C10 C 0.3834(2) 0.9099(2) 0.32129(18) 0.0430(5) Uani 1 1 d . .
H10A H 0.4377 0.9655 0.3853 0.052 Uiso 1 1 calc R U
H10B H 0.4456 0.8492 0.2911 0.052 Uiso 1 1 calc R U
C11 C 0.3402(2) 1.0057(2) 0.23630(17) 0.0401(5) Uani 1 1 d . .
C12 C 0.4212(3) 1.1728(3) 0.1146(2) 0.0670(8) Uani 1 1 d . .
H12A H 0.3855 1.2530 0.1476 0.080 Uiso 1 1 calc R U
H12B H 0.3474 1.1249 0.0576 0.080 Uiso 1 1 calc R U
C13 C 0.5546(4) 1.2204(4) 0.0662(3) 0.0963(12) Uani 1 1 d . .
H13A H 0.5359 1.2840 0.0104 0.144 Uiso 1 1 calc R U
H13B H 0.6268 1.2680 0.1230 0.144 Uiso 1 1 calc R U
H13C H 0.5888 1.1404 0.0334 0.144 Uiso 1 1 calc R U
C14 C 0.0658(3) 0.2755(2) 0.08166(18) 0.0477(5) Uani 1 1 d . .
H14 H 0.0355 0.2287 0.1421 0.057 Uiso 1 1 calc R U
C15 C 0.0167(3) 0.2159(3) -0.0228(2) 0.0587(6) Uani 1 1 d . .
H15 H -0.0465 0.1305 -0.0330 0.070 Uiso 1 1 calc R U
C16 C 0.0616(3) 0.2831(3) -0.11106(19) 0.0604(7) Uani 1 1 d . .
H16 H 0.0309 0.2445 -0.1830 0.073 Uiso 1 1 calc R U
C17 C 0.1522(3) 0.4078(3) -0.09207(19) 0.0682(8) Uani 1 1 d . .
H17 H 0.1834 0.4570 -0.1512 0.082 Uiso 1 1 calc R U
C18 C 0.1973(3) 0.4609(3) 0.01370(18) 0.0533(6) Uani 1 1 d . .
H18 H 0.2610 0.5459 0.0256 0.064 Uiso 1 1 calc R U
Cl1 Cl 0.00015(5) 0.41963(5) 0.31568(4) 0.04140(12) Uani 1 1 d . .
Cl2 Cl 0.45166(5) 0.56293(6) 0.21566(4) 0.04280(12) Uani 1 1 d . .
N1 N 0.31949(16) 0.52556(15) 0.50007(12) 0.0284(3) Uani 1 1 d . .
N2 N 0.29073(16) 0.72003(15) 0.43338(12) 0.0298(3) Uani 1 1 d . .
N3 N 0.15428(18) 0.39672(17) 0.09991(12) 0.0354(3) Uani 1 1 d . .
O1 O 0.27670(16) 0.09326(14) 0.54362(12) 0.0417(3) Uani 1 1 d . .
O2 O 0.08453(15) 0.10661(14) 0.63347(12) 0.0394(3) Uani 1 1 d . .
O3 O 0.21829(18) 1.0156(2) 0.20559(16) 0.0643(5) Uani 1 1 d . .
O4 O 0.45286(17) 1.07702(17) 0.19842(15) 0.0537(4) Uani 1 1 d . .
Pd1 Pd 0.22212(2) 0.48932(2) 0.25985(2) 0.02859(7) Uani 1 1 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'
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_publ_flag
N1 C1 N2 105.71(15) y
N1 C1 Pd1 128.72(13) y
N2 C1 Pd1 125.57(13) y
C3 C2 N1 106.67(16) y
C3 C2 H2 126.7 n
N1 C2 H2 126.7 n
C2 C3 N2 107.02(16) y
C2 C3 H3 126.5 n
N2 C3 H3 126.5 n
N1 C4 C5 111.21(14) y
N1 C4 H4A 109.4 n
C5 C4 H4A 109.4 n
N1 C4 H4B 109.4 n
C5 C4 H4B 109.4 n
H4A C4 H4B 108.0 n
C6 C5 C4 111.15(15) y
C6 C5 H5A 109.4 n
C4 C5 H5A 109.4 n
C6 C5 H5B 109.4 n
C4 C5 H5B 109.4 n
H5A C5 H5B 108.0 n
O1 C6 O2 124.30(16) y
O1 C6 C5 124.87(17) y
O2 C6 C5 110.83(15) y
O2 C7 C8 110.06(17) n
O2 C7 H7A 109.6 n
C8 C7 H7A 109.6 n
O2 C7 H7B 109.6 n
C8 C7 H7B 109.6 n
H7A C7 H7B 108.2 n
C7 C8 H8A 109.5 n
C7 C8 H8B 109.5 n
H8A C8 H8B 109.5 n
C7 C8 H8C 109.5 n
H8A C8 H8C 109.5 n
H8B C8 H8C 109.5 n
N2 C9 C10 112.65(15) y
N2 C9 H9A 109.1 n
C10 C9 H9A 109.1 n
N2 C9 H9B 109.1 n
C10 C9 H9B 109.1 n
H9A C9 H9B 107.8 n
C11 C10 C9 110.76(17) y
C11 C10 H10A 109.5 n
C9 C10 H10A 109.5 n
C11 C10 H10B 109.5 n
C9 C10 H10B 109.5 n
H10A C10 H10B 108.1 n
O3 C11 O4 123.87(19) y
O3 C11 C10 124.2(2) y
O4 C11 C10 111.91(18) y
O4 C12 C13 108.2(2) n
O4 C12 H12A 110.1 n
C13 C12 H12A 110.1 n
O4 C12 H12B 110.1 n
C13 C12 H12B 110.1 n
H12A C12 H12B 108.4 n
C12 C13 H13A 109.5 n
C12 C13 H13B 109.5 n
H13A C13 H13B 109.5 n
C12 C13 H13C 109.5 n
H13A C13 H13C 109.5 n
H13B C13 H13C 109.5 n
N3 C14 C15 122.5(2) y
N3 C14 H14 118.7 n
C15 C14 H14 118.7 n
C16 C15 C14 119.0(2) n
C16 C15 H15 120.5 n
C14 C15 H15 120.5 n
C17 C16 C15 118.4(2) n
C17 C16 H16 120.8 n
C15 C16 H16 120.8 n
C16 C17 C18 119.7(2) n
C16 C17 H17 120.2 n
C18 C17 H17 120.2 n
N3 C18 C17 122.5(2) y
N3 C18 H18 118.8 n
C17 C18 H18 118.8 n
C1 N1 C2 110.38(15) y
C1 N1 C4 124.80(15) y
C2 N1 C4 124.76(15) y
C1 N2 C3 110.22(15) y
C1 N2 C9 124.11(15) y
C3 N2 C9 125.63(15) y
C18 N3 C14 117.99(18) y
C18 N3 Pd1 120.12(15) y
C14 N3 Pd1 121.87(14) y
C6 O2 C7 116.48(14) y
C11 O4 C12 115.81(18) y
C1 Pd1 N3 177.50(6) y
C1 Pd1 Cl1 87.60(5) y
N3 Pd1 Cl1 91.87(5) y
C1 Pd1 Cl2 88.76(5) y
N3 Pd1 Cl2 91.81(5) y
Cl1 Pd1 Cl2 176.213(17) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.343(2) y
C1 N2 1.348(2) y
C1 Pd1 1.9578(17) y
C2 C3 1.343(3) y
C2 N1 1.387(2) y
C2 H2 0.9400 n
C3 N2 1.382(2) y
C3 H3 0.9400 n
C4 N1 1.465(2) y
C4 C5 1.509(3) n
C4 H4A 0.9800 n
C4 H4B 0.9800 n
C5 C6 1.505(2) y
C5 H5A 0.9800 n
C5 H5B 0.9800 n
C6 O1 1.202(2) y
C6 O2 1.335(2) y
C7 O2 1.463(2) y
C7 C8 1.506(3) n
C7 H7A 0.9800 n
C7 H7B 0.9800 n
C8 H8A 0.9700 n
C8 H8B 0.9700 n
C8 H8C 0.9700 n
C9 N2 1.465(2) y
C9 C10 1.506(3) n
C9 H9A 0.9800 n
C9 H9B 0.9800 n
C10 C11 1.505(3) y
C10 H10A 0.9800 n
C10 H10B 0.9800 n
C11 O3 1.201(3) y
C11 O4 1.323(3) y
C12 O4 1.466(3) y
C12 C13 1.476(4) n
C12 H12A 0.9800 n
C12 H12B 0.9800 n
C13 H13A 0.9700 n
C13 H13B 0.9700 n
C13 H13C 0.9700 n
C14 N3 1.330(3) y
C14 C15 1.383(3) y
C14 H14 0.9400 n
C15 C16 1.370(4) y
C15 H15 0.9400 n
C16 C17 1.366(4) y
C16 H16 0.9400 n
C17 C18 1.372(3) y
C17 H17 0.9400 n
C18 N3 1.328(3) y
C18 H18 0.9400 n
Cl1 Pd1 2.2988(5) y
Cl2 Pd1 2.3167(5) y
N3 Pd1 2.1102(15) 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_publ_flag
N1 C2 C3 N2 0.2(2) n
N1 C4 C5 C6 -178.29(15) y
C4 C5 C6 O1 -5.8(3) y
C4 C5 C6 O2 174.20(16) y
N2 C9 C10 C11 176.20(17) y
C9 C10 C11 O3 4.1(3) y
C9 C10 C11 O4 -175.28(19) y
N3 C14 C15 C16 0.6(4) n
C14 C15 C16 C17 -0.8(4) n
C15 C16 C17 C18 1.1(4) n
C16 C17 C18 N3 -1.2(4) n
N2 C1 N1 C2 0.1(2) n
Pd1 C1 N1 C2 179.75(13) y
N2 C1 N1 C4 177.20(15) y
Pd1 C1 N1 C4 -3.2(3) y
C3 C2 N1 C1 -0.2(2) n
C3 C2 N1 C4 -177.28(16) y
C5 C4 N1 C1 -102.2(2) y
C5 C4 N1 C2 74.5(2) y
N1 C1 N2 C3 0.0(2) n
Pd1 C1 N2 C3 -179.65(13) y
N1 C1 N2 C9 -177.92(16) y
Pd1 C1 N2 C9 2.4(3) y
C2 C3 N2 C1 -0.1(2) n
C2 C3 N2 C9 177.76(17) y
C10 C9 N2 C1 -105.0(2) y
C10 C9 N2 C3 77.4(2) y
C17 C18 N3 C14 1.0(4) n
C17 C18 N3 Pd1 -177.5(2) y
C15 C14 N3 C18 -0.7(3) n
C15 C14 N3 Pd1 177.83(18) y
O1 C6 O2 C7 3.9(3) y
C5 C6 O2 C7 -176.13(16) y
C8 C7 O2 C6 81.3(2) y
O3 C11 O4 C12 0.3(4) y
C10 C11 O4 C12 179.7(2) y
C13 C12 O4 C11 -168.5(3) y
