#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:44:48 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179762 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/58/7005889.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_7005889
loop_
_publ_author_name
'Ray, Lipika'
'Shaikh, Mobin M.'
'Ghosh, Prasenjit'
_publ_section_title
;
 Air-stable, convenient to handle Pd based PEPPSI (pyridine enhanced
 precatalyst preparation, stabilization and initiation) themed
 precatalysts of N/O-functionalized N-heterocyclic carbenes and its
 utility in Suzuki-Miyaura cross-coupling reaction.
;
_journal_issue                   40
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4546
_journal_page_last               4555
_journal_paper_doi               10.1039/b706607d
_journal_year                    2007
_chemical_formula_sum            'C21 H26 Cl2 N4 O Pd'
_chemical_formula_weight         527.76
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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-97
_cell_angle_alpha                107.068(14)
_cell_angle_beta                 111.852(19)
_cell_angle_gamma                100.997(14)
_cell_formula_units_Z            2
_cell_length_a                   10.829(2)
_cell_length_b                   11.2668(15)
_cell_length_c                   11.429(2)
_cell_measurement_reflns_used    8313
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.5065
_cell_measurement_theta_min      3.0515
_cell_volume                     1164.4(4)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9996
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    1.045
_exptl_absorpt_correction_T_max  0.7801
_exptl_absorpt_correction_T_min  0.7111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.088
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0724P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                3400
_reflns_number_total             4090
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b706607d.txt
_cod_data_source_block           pg082
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1164.3(4)
_cod_database_code               7005889
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.25456(3) 0.48867(2) 1.14091(2) 0.02347(12) Uani 1 1 d . . .
Cl2 Cl 0.32817(10) 0.31721(8) 1.17038(9) 0.0358(2) Uani 1 1 d . . .
Cl1 Cl 0.17521(9) 0.65904(8) 1.11361(8) 0.0309(2) Uani 1 1 d . . .
O1 O 0.0202(3) 0.3198(3) 1.3703(3) 0.0517(8) Uani 1 1 d . . .
N1 N 0.3936(3) 0.6216(2) 1.4464(3) 0.0232(6) Uani 1 1 d . . .
N2 N 0.1688(3) 0.5472(2) 1.3644(3) 0.0235(6) Uani 1 1 d . . .
N3 N -0.1314(3) 0.2512(3) 1.1457(3) 0.0295(7) Uani 1 1 d . . .
N4 N 0.2391(3) 0.4239(3) 0.9433(3) 0.0255(6) Uani 1 1 d . . .
C1 C 0.2724(3) 0.5533(3) 1.3272(3) 0.0224(7) Uani 1 1 d . . .
C2 C 0.3613(4) 0.6585(3) 1.5553(3) 0.0273(7) Uani 1 1 d . . .
H2 H 0.4257 0.7072 1.6474 0.033 Uiso 1 1 calc R . .
C3 C 0.2216(4) 0.6116(3) 1.5039(3) 0.0266(7) Uani 1 1 d . . .
H3 H 0.1698 0.6207 1.5531 0.032 Uiso 1 1 calc R . .
C4 C 0.5365(3) 0.6556(3) 1.4587(3) 0.0261(7) Uani 1 1 d . . .
H4A H 0.5335 0.6012 1.3736 0.031 Uiso 1 1 calc R . .
H4B H 0.5966 0.6349 1.5317 0.031 Uiso 1 1 calc R . .
C5 C 0.6008(3) 0.7973(3) 1.4886(3) 0.0259(7) Uani 1 1 d . . .
C6 C 0.7121(4) 0.8814(3) 1.6150(4) 0.0340(8) Uani 1 1 d . . .
H6 H 0.7471 0.8498 1.6828 0.041 Uiso 1 1 calc R . .
C7 C 0.7719(4) 1.0122(3) 1.6417(4) 0.0411(10) Uani 1 1 d . . .
H7 H 0.8475 1.0676 1.7272 0.049 Uiso 1 1 calc R . .
C8 C 0.7215(4) 1.0613(4) 1.5440(4) 0.0411(9) Uani 1 1 d . . .
H8 H 0.7627 1.1493 1.5627 0.049 Uiso 1 1 calc R . .
C9 C 0.6100(4) 0.9796(4) 1.4188(4) 0.0420(10) Uani 1 1 d . . .
H9 H 0.5743 1.0125 1.3524 0.050 Uiso 1 1 calc R . .
C10 C 0.5500(4) 0.8478(3) 1.3903(4) 0.0347(8) Uani 1 1 d . . .
H10 H 0.4749 0.7928 1.3045 0.042 Uiso 1 1 calc R . .
C11 C 0.0204(3) 0.4773(3) 1.2690(4) 0.0278(7) Uani 1 1 d . . .
H11A H 0.0047 0.4699 1.1775 0.033 Uiso 1 1 calc R . .
H11B H -0.0354 0.5273 1.2956 0.033 Uiso 1 1 calc R . .
C12 C -0.0283(3) 0.3399(3) 1.2661(3) 0.0264(7) Uani 1 1 d . . .
C13 C -0.1991(4) 0.1115(3) 1.1087(4) 0.0352(9) Uani 1 1 d . . .
C14 C -0.3088(6) 0.0527(4) 0.9596(4) 0.0714(16) Uani 1 1 d . . .
H14A H -0.3746 0.0996 0.9477 0.107 Uiso 1 1 calc R . .
H14B H -0.3583 -0.0385 0.9334 0.107 Uiso 1 1 calc R . .
H14C H -0.2630 0.0595 0.9031 0.107 Uiso 1 1 calc R . .
C15 C -0.0917(6) 0.0450(5) 1.1236(8) 0.114(3) Uani 1 1 d . . .
H15A H -0.0441 0.0616 1.0710 0.171 Uiso 1 1 calc R . .
H15B H -0.1374 -0.0483 1.0907 0.171 Uiso 1 1 calc R . .
H15C H -0.0242 0.0786 1.2188 0.171 Uiso 1 1 calc R . .
C16 C -0.2675(8) 0.0955(6) 1.1974(6) 0.111(3) Uani 1 1 d . . .
H16A H -0.1963 0.1276 1.2910 0.166 Uiso 1 1 calc R . .
H16B H -0.3191 0.0039 1.1664 0.166 Uiso 1 1 calc R . .
H16C H -0.3312 0.1447 1.1920 0.166 Uiso 1 1 calc R . .
C17 C 0.3168(4) 0.5007(4) 0.9091(4) 0.0318(8) Uani 1 1 d . . .
H17 H 0.3787 0.5837 0.9754 0.038 Uiso 1 1 calc R . .
C18 C 0.3097(4) 0.4629(4) 0.7807(4) 0.0398(9) Uani 1 1 d . . .
H18 H 0.3662 0.5188 0.7607 0.048 Uiso 1 1 calc R . .
C19 C 0.2173(4) 0.3403(4) 0.6817(4) 0.0418(10) Uani 1 1 d . . .
H19 H 0.2092 0.3122 0.5933 0.050 Uiso 1 1 calc R . .
C20 C 0.1386(4) 0.2618(4) 0.7163(4) 0.0399(9) Uani 1 1 d . . .
H20 H 0.0758 0.1786 0.6513 0.048 Uiso 1 1 calc R . .
C21 C 0.1511(4) 0.3047(3) 0.8474(4) 0.0350(8) Uani 1 1 d . . .
H21 H 0.0969 0.2492 0.8697 0.042 Uiso 1 1 calc R . .
H3N H -0.144(4) 0.275(3) 1.092(4) 0.020(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
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'
Cl Cl 0.1484 0.1585 '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
C1 Pd1 N4 178.63(11) . . ?
C1 Pd1 Cl2 91.24(9) . . ?
N4 Pd1 Cl2 89.44(8) . . ?
C1 Pd1 Cl1 87.62(9) . . ?
N4 Pd1 Cl1 91.74(8) . . ?
Cl2 Pd1 Cl1 178.14(3) . . ?
C1 N1 C2 109.4(3) . . ?
C1 N1 C4 125.6(3) . . ?
C2 N1 C4 124.9(3) . . ?
C1 N2 C3 111.3(3) . . ?
C1 N2 C11 123.8(3) . . ?
C3 N2 C11 124.8(3) . . ?
C12 N3 C13 127.7(3) . . ?
C12 N3 H3N 113(3) . . ?
C13 N3 H3N 118(3) . . ?
C17 N4 C21 117.9(3) . . ?
C17 N4 Pd1 120.9(2) . . ?
C21 N4 Pd1 121.2(2) . . ?
N2 C1 N1 105.1(3) . . ?
N2 C1 Pd1 127.9(2) . . ?
N1 C1 Pd1 126.9(2) . . ?
C3 C2 N1 107.5(3) . . ?
C3 C2 H2 126.3 . . ?
N1 C2 H2 126.3 . . ?
C2 C3 N2 106.7(3) . . ?
C2 C3 H3 126.7 . . ?
N2 C3 H3 126.7 . . ?
N1 C4 C5 113.7(3) . . ?
N1 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
N1 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C10 118.3(3) . . ?
C6 C5 C4 120.7(3) . . ?
C10 C5 C4 120.9(3) . . ?
C5 C6 C7 120.5(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.9(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 120.7(3) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
N2 C11 C12 111.5(3) . . ?
N2 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N2 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
O1 C12 N3 124.9(3) . . ?
O1 C12 C11 120.7(3) . . ?
N3 C12 C11 114.3(3) . . ?
N3 C13 C15 109.2(4) . . ?
N3 C13 C16 110.4(4) . . ?
C15 C13 C16 110.6(5) . . ?
N3 C13 C14 107.5(3) . . ?
C15 C13 C14 108.9(4) . . ?
C16 C13 C14 110.2(4) . . ?
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 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C17 C18 123.0(3) . . ?
N4 C17 H17 118.5 . . ?
C18 C17 H17 118.5 . . ?
C17 C18 C19 118.8(4) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C20 C19 C18 118.4(4) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C19 C20 C21 120.3(4) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
N4 C21 C20 121.7(4) . . ?
N4 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
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
Pd1 C1 1.957(3) . ?
Pd1 N4 2.089(3) . ?
Pd1 Cl2 2.2913(9) . ?
Pd1 Cl1 2.3026(9) . ?
O1 C12 1.218(4) . ?
N1 C1 1.356(4) . ?
N1 C2 1.385(4) . ?
N1 C4 1.463(4) . ?
N2 C1 1.337(4) . ?
N2 C3 1.371(4) . ?
N2 C11 1.449(4) . ?
N3 C12 1.328(5) . ?
N3 C13 1.461(5) . ?
N3 H3N 0.72(3) . ?
N4 C17 1.333(5) . ?
N4 C21 1.336(4) . ?
C2 C3 1.328(5) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.493(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.380(5) . ?
C5 C10 1.387(5) . ?
C6 C7 1.382(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.369(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.524(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 C15 1.484(7) . ?
C13 C16 1.491(6) . ?
C13 C14 1.511(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.370(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.355(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 Pd1 N4 C17 1(5) . . . . ?
Cl2 Pd1 N4 C17 -118.9(2) . . . . ?
Cl1 Pd1 N4 C17 62.6(2) . . . . ?
C1 Pd1 N4 C21 -179(100) . . . . ?
Cl2 Pd1 N4 C21 61.2(3) . . . . ?
Cl1 Pd1 N4 C21 -117.3(3) . . . . ?
C3 N2 C1 N1 0.9(3) . . . . ?
C11 N2 C1 N1 -177.2(3) . . . . ?
C3 N2 C1 Pd1 -175.5(2) . . . . ?
C11 N2 C1 Pd1 6.4(4) . . . . ?
C2 N1 C1 N2 -1.2(3) . . . . ?
C4 N1 C1 N2 -179.1(3) . . . . ?
C2 N1 C1 Pd1 175.3(2) . . . . ?
C4 N1 C1 Pd1 -2.7(4) . . . . ?
N4 Pd1 C1 N2 133(5) . . . . ?
Cl2 Pd1 C1 N2 -107.3(3) . . . . ?
Cl1 Pd1 C1 N2 71.3(3) . . . . ?
N4 Pd1 C1 N1 -42(5) . . . . ?
Cl2 Pd1 C1 N1 77.1(3) . . . . ?
Cl1 Pd1 C1 N1 -104.4(3) . . . . ?
C1 N1 C2 C3 1.0(4) . . . . ?
C4 N1 C2 C3 179.0(3) . . . . ?
N1 C2 C3 N2 -0.4(4) . . . . ?
C1 N2 C3 C2 -0.3(4) . . . . ?
C11 N2 C3 C2 177.8(3) . . . . ?
C1 N1 C4 C5 105.2(3) . . . . ?
C2 N1 C4 C5 -72.4(4) . . . . ?
N1 C4 C5 C6 110.3(4) . . . . ?
N1 C4 C5 C10 -69.4(4) . . . . ?
C10 C5 C6 C7 -0.8(6) . . . . ?
C4 C5 C6 C7 179.5(3) . . . . ?
C5 C6 C7 C8 0.5(6) . . . . ?
C6 C7 C8 C9 0.3(6) . . . . ?
C7 C8 C9 C10 -1.0(6) . . . . ?
C8 C9 C10 C5 0.8(6) . . . . ?
C6 C5 C10 C9 0.1(5) . . . . ?
C4 C5 C10 C9 179.9(4) . . . . ?
C1 N2 C11 C12 97.0(4) . . . . ?
C3 N2 C11 C12 -80.9(4) . . . . ?
C13 N3 C12 O1 -5.7(6) . . . . ?
C13 N3 C12 C11 178.8(3) . . . . ?
N2 C11 C12 O1 35.0(5) . . . . ?
N2 C11 C12 N3 -149.3(3) . . . . ?
C12 N3 C13 C15 -61.4(6) . . . . ?
C12 N3 C13 C16 60.5(6) . . . . ?
C12 N3 C13 C14 -179.3(4) . . . . ?
C21 N4 C17 C18 0.3(5) . . . . ?
Pd1 N4 C17 C18 -179.6(3) . . . . ?
N4 C17 C18 C19 0.5(5) . . . . ?
C17 C18 C19 C20 -0.8(6) . . . . ?
C18 C19 C20 C21 0.2(6) . . . . ?
C17 N4 C21 C20 -0.9(5) . . . . ?
Pd1 N4 C21 C20 179.0(3) . . . . ?
C19 C20 C21 N4 0.6(6) . . . . ?
