#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:18:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178621 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/32/4073299.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_4073299
loop_
_publ_author_name
'Chernyshova, Eleonora S.'
'Goddard, Richard'
'Pörschke, Klaus-Richard'
_publ_section_title
;
 Mononuclear NHC−Pd−π-Allyl Complexes Containing Weakly
 Coordinating Ligands
;
_journal_issue                   13
_journal_name_full               Organometallics
_journal_page_first              3236
_journal_paper_doi               10.1021/om0702274
_journal_volume                  26
_journal_year                    2007
_chemical_compound_source        dichloromethane/pentane
_chemical_formula_moiety         'C31 H43 Cl2 N2 Pd 1+, P F6 1-, 2(C H2 Cl2)'
_chemical_formula_sum            'C33 H47 Cl6 F6 N2 P Pd'
_chemical_formula_weight         935.80
_chemical_melting_point          ?
_chemical_name_systematic
; 
 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene-
 (dichloromethane-Cl)-(η³-allyl)palladium hexafluorophosphate
 di-dichloromethane solvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0
_cell_angle_beta                 93.908(1)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   12.7245(2)
_cell_length_b                   24.8421(5)
_cell_length_c                   12.9234(2)
_cell_measurement_reflns_used    372849
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.51
_cell_measurement_theta_min      2.91
_cell_volume                     4075.63(12)
_computing_cell_refinement       'Denzo / Scalepack (Otwinowski 1997)'
_computing_data_collection       'Collect software (Nonius, 1998)'
_computing_data_reduction        'Denzo / Scalepack (Otwinowski 1997)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD ω-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.3 mm focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            92230
_diffrn_reflns_theta_full        31.47
_diffrn_reflns_theta_max         31.47
_diffrn_reflns_theta_min         2.92
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.942
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.9068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack, Otwinowski (1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.419
_refine_diff_density_min         -1.175
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         13496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.189
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0610
_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)+(0.0298P)²+13.5925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                11559
_reflns_number_total             13496
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om0702274si20070309_074405.cif
_cod_data_source_block           11c(PF6)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4073299
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5173(3) 0.26177(15) 0.3313(3) 0.0294(8) Uani 1 1 d . A 1
H1A H 0.5500 0.2675 0.2665 0.035 Uiso 1 1 calc R A 1
H1B H 0.4737 0.2918 0.3502 0.035 Uiso 1 1 calc R A 1
C2A C 0.5787(4) 0.2398(2) 0.4086(4) 0.0246(13) Uani 0.720(12) 1 d P A 1
H2 H 0.6513 0.2306 0.3943 0.030 Uiso 0.720(12) 1 calc PR A 1
C2B C 0.5129(9) 0.2528(5) 0.4457(9) 0.021(3) Uiso 0.280(12) 1 d P A 2
C3 C 0.5381(3) 0.21720(18) 0.4968(3) 0.0353(9) Uani 1 1 d . A 1
H3A H 0.4981 0.2409 0.5389 0.042 Uiso 1 1 calc R A 1
H3B H 0.5835 0.1924 0.5368 0.042 Uiso 1 1 calc R A 1
C4 C 0.3946(2) 0.17488(11) 0.2038(2) 0.0131(5) Uani 1 1 d . A 1
C5 C 0.3079(2) 0.18773(12) 0.0470(2) 0.0170(5) Uani 1 1 d . A 1
H5 H 0.2629 0.2027 -0.0050 0.020 Uiso 1 1 calc R A 1
C6 C 0.3686(2) 0.14381(12) 0.0385(2) 0.0163(5) Uani 1 1 d . A 1
H6 H 0.3744 0.1227 -0.0203 0.020 Uiso 1 1 calc R A 1
C7 C 0.2688(2) 0.25188(11) 0.1878(2) 0.0142(5) Uani 1 1 d . A 1
C8 C 0.2996(2) 0.30401(11) 0.1609(2) 0.0154(5) Uani 1 1 d . A 1
C9 C 0.2392(3) 0.34662(12) 0.1951(3) 0.0195(6) Uani 1 1 d . A 1
H9 H 0.2575 0.3818 0.1793 0.023 Uiso 1 1 calc R A 1
C10 C 0.1523(3) 0.33751(13) 0.2520(3) 0.0211(6) Uani 1 1 d . A 1
H10 H 0.1123 0.3664 0.2727 0.025 Uiso 1 1 calc R A 1
C11 C 0.1249(3) 0.28538(13) 0.2784(2) 0.0198(6) Uani 1 1 d . A 1
H11 H 0.0669 0.2797 0.3172 0.024 Uiso 1 1 calc R A 1
C12 C 0.1832(2) 0.24145(12) 0.2472(2) 0.0169(5) Uani 1 1 d . A 1
C13 C 0.3911(2) 0.31555(12) 0.0941(2) 0.0179(5) Uani 1 1 d . A 1
H13 H 0.4372 0.2839 0.0967 0.021 Uiso 1 1 calc R A 1
C14 C 0.4570(3) 0.36423(13) 0.1328(3) 0.0246(7) Uani 1 1 d . A 1
H14A H 0.5135 0.3698 0.0884 0.037 Uiso 1 1 calc R A 1
H14B H 0.4854 0.3576 0.2023 0.037 Uiso 1 1 calc R A 1
H14C H 0.4131 0.3957 0.1318 0.037 Uiso 1 1 calc R A 1
C15 C 0.3512(3) 0.32439(14) -0.0190(3) 0.0235(7) Uani 1 1 d . A 1
H15A H 0.4098 0.3315 -0.0599 0.035 Uiso 1 1 calc R A 1
H15B H 0.3038 0.3545 -0.0233 0.035 Uiso 1 1 calc R A 1
H15C H 0.3149 0.2927 -0.0447 0.035 Uiso 1 1 calc R A 1
C16 C 0.1494(2) 0.18496(14) 0.2761(3) 0.0210(6) Uani 1 1 d . A 1
H16 H 0.2035 0.1598 0.2553 0.025 Uiso 1 1 calc R A 1
C17 C 0.0455(3) 0.16997(18) 0.2163(4) 0.0393(10) Uani 1 1 d . A 1
H17A H 0.0253 0.1343 0.2353 0.059 Uiso 1 1 calc R A 1
H17B H 0.0544 0.1713 0.1432 0.059 Uiso 1 1 calc R A 1
H17C H -0.0083 0.1950 0.2330 0.059 Uiso 1 1 calc R A 1
C18 C 0.1420(3) 0.17927(16) 0.3939(3) 0.0308(8) Uani 1 1 d . A 1
H18A H 0.1206 0.1433 0.4096 0.046 Uiso 1 1 calc R A 1
H18B H 0.0912 0.2044 0.4168 0.046 Uiso 1 1 calc R A 1
H18C H 0.2096 0.1865 0.4287 0.046 Uiso 1 1 calc R A 1
C19 C 0.4893(2) 0.09109(11) 0.1621(2) 0.0150(5) Uani 1 1 d . A 1
C20 C 0.4424(3) 0.04064(12) 0.1756(2) 0.0179(6) Uani 1 1 d . A 1
C21 C 0.5097(3) -0.00232(13) 0.2020(3) 0.0229(6) Uani 1 1 d . A 1
H21 H 0.4813 -0.0364 0.2107 0.027 Uiso 1 1 calc R A 1
C22 C 0.6175(3) 0.00465(14) 0.2155(3) 0.0257(7) Uani 1 1 d . A 1
H22 H 0.6605 -0.0244 0.2347 0.031 Uiso 1 1 calc R A 1
C23 C 0.6617(3) 0.05495(14) 0.2004(3) 0.0228(6) Uani 1 1 d . A 1
H23 H 0.7344 0.0590 0.2089 0.027 Uiso 1 1 calc R A 1
C24 C 0.5991(2) 0.09937(12) 0.1730(2) 0.0164(5) Uani 1 1 d . A 1
C25 C 0.3239(3) 0.03163(13) 0.1573(3) 0.0213(6) Uani 1 1 d . A 1
H25 H 0.2889 0.0668 0.1580 0.026 Uiso 1 1 calc R A 1
C26 C 0.2994(4) 0.00595(18) 0.0502(3) 0.0377(9) Uani 1 1 d . A 1
H26A H 0.2248 0.0005 0.0389 0.057 Uiso 1 1 calc R A 1
H26B H 0.3348 -0.0281 0.0473 0.057 Uiso 1 1 calc R A 1
H26C H 0.3231 0.0294 -0.0025 0.057 Uiso 1 1 calc R A 1
C27 C 0.2797(3) -0.00353(16) 0.2413(3) 0.0307(8) Uani 1 1 d . A 1
H27A H 0.2052 -0.0079 0.2269 0.046 Uiso 1 1 calc R A 1
H27B H 0.2929 0.0134 0.3077 0.046 Uiso 1 1 calc R A 1
H27C H 0.3133 -0.0381 0.2420 0.046 Uiso 1 1 calc R A 1
C28 C 0.6467(3) 0.15365(13) 0.1491(3) 0.0188(6) Uani 1 1 d . A 1
H28 H 0.6015 0.1817 0.1756 0.023 Uiso 1 1 calc R A 1
C29 C 0.7577(3) 0.16124(15) 0.2003(3) 0.0285(7) Uani 1 1 d . A 1
H29A H 0.7839 0.1961 0.1827 0.043 Uiso 1 1 calc R A 1
H29B H 0.8034 0.1339 0.1761 0.043 Uiso 1 1 calc R A 1
H29C H 0.7555 0.1585 0.2742 0.043 Uiso 1 1 calc R A 1
C30 C 0.6494(3) 0.16164(16) 0.0308(3) 0.0300(8) Uani 1 1 d . A 1
H30A H 0.6797 0.1961 0.0171 0.045 Uiso 1 1 calc R A 1
H30B H 0.5790 0.1600 -0.0008 0.045 Uiso 1 1 calc R A 1
H30C H 0.6913 0.1338 0.0026 0.045 Uiso 1 1 calc R A 1
C31 C 0.4558(3) 0.08215(15) 0.5347(3) 0.0251(7) Uani 1 1 d . A 1
H31A H 0.4586 0.1113 0.5847 0.030 Uiso 1 1 calc R A 1
H31B H 0.4212 0.0517 0.5649 0.030 Uiso 1 1 calc R A 1
C32 C 0.8913(4) -0.01271(16) 0.3937(3) 0.0346(9) Uani 1 1 d . B 1
H32A H 0.9508 -0.0361 0.4119 0.041 Uiso 1 1 calc R B 1
H32B H 0.8489 -0.0296 0.3375 0.041 Uiso 1 1 calc R B 1
C33 C 0.0416(4) 0.08201(19) 0.9479(4) 0.0403(10) Uani 1 1 d . C 1
H33A H 0.0680 0.0718 1.0173 0.048 Uiso 1 1 calc R C 1
H33B H 0.0891 0.1088 0.9226 0.048 Uiso 1 1 calc R C 1
Cl1 Cl 0.38177(7) 0.10297(4) 0.41911(7) 0.02780(18) Uani 1 1 d . A 1
Cl2 Cl 0.58413(8) 0.06392(4) 0.50746(9) 0.0370(2) Uani 1 1 d . A 1
Cl3 Cl 0.93745(10) 0.04970(4) 0.35196(9) 0.0439(3) Uani 1 1 d . B 1
Cl4 Cl 0.81528(9) -0.00534(5) 0.50183(10) 0.0477(3) Uani 1 1 d . B 1
Cl5 Cl -0.08408(9) 0.11016(5) 0.95282(11) 0.0473(3) Uani 1 1 d . C 1
Cl6 Cl 0.04062(10) 0.02490(5) 0.86631(9) 0.0451(3) Uani 1 1 d . C 1
F1 F 0.39027(18) 0.13055(9) 0.78160(18) 0.0320(5) Uani 1 1 d . D 1
F2 F 0.3227(2) 0.21366(9) 0.80664(17) 0.0317(5) Uani 1 1 d . D 1
F3 F 0.2188(2) 0.13998(11) 0.81673(19) 0.0395(6) Uani 1 1 d . D 1
F4 F 0.19372(18) 0.19753(10) 0.67983(19) 0.0342(5) Uani 1 1 d . D 1
F5 F 0.26127(19) 0.11414(9) 0.65595(18) 0.0336(5) Uani 1 1 d . D 1
F6 F 0.36459(18) 0.18806(9) 0.64617(17) 0.0299(5) Uani 1 1 d . D 1
N1 N 0.3247(2) 0.20645(10) 0.14756(19) 0.0139(4) Uani 1 1 d . A 1
N2 N 0.4211(2) 0.13629(10) 0.13531(19) 0.0138(4) Uani 1 1 d . A 1
P1 P 0.29126(7) 0.16414(3) 0.73078(7) 0.01933(16) Uani 1 1 d . D 1
Pd1 Pd 0.455728(18) 0.185321(9) 0.353351(17) 0.01401(6) Uani 1 1 d . A 1
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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 '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
C2A C1 Pd1 74.5(3) y
C1 C2A C3 122.7(5) y
C1 C2A Pd1 68.6(2) y
C3 C2A Pd1 73.6(2) y
C2A C3 Pd1 69.0(2) y
N1 C4 N2 103.9(2) y
N1 C4 Pd1 128.6(2) y
N2 C4 Pd1 127.3(2) y
C6 C5 N1 107.2(3) y
C5 C6 N2 106.2(3) y
C12 C7 C8 123.2(3) y
C12 C7 N1 118.2(3) y
C8 C7 N1 118.5(3) y
C9 C8 C7 116.8(3) y
C9 C8 C13 119.7(3) y
C7 C8 C13 123.5(3) y
C10 C9 C8 121.3(3) y
C9 C10 C11 120.3(3) y
C10 C11 C12 120.7(3) y
C11 C12 C7 117.6(3) y
C11 C12 C16 119.0(3) y
C7 C12 C16 123.3(3) y
C8 C13 C15 110.7(3) y
C8 C13 C14 112.6(3) y
C15 C13 C14 109.7(3) y
C12 C16 C17 110.5(3) y
C12 C16 C18 111.4(3) y
C17 C16 C18 111.6(3) y
C20 C19 C24 123.0(3) y
C20 C19 N2 118.0(3) y
C24 C19 N2 119.0(3) y
C21 C20 C19 117.0(3) y
C21 C20 C25 120.6(3) y
C19 C20 C25 122.3(3) y
C22 C21 C20 121.5(3) y
C21 C22 C23 120.2(3) y
C22 C23 C24 121.2(3) y
C23 C24 C19 117.1(3) y
C23 C24 C28 121.7(3) y
C19 C24 C28 121.1(3) y
C20 C25 C27 112.4(3) y
C20 C25 C26 109.8(3) y
C27 C25 C26 109.9(3) y
C24 C28 C29 113.0(3) y
C24 C28 C30 110.6(3) y
C29 C28 C30 109.3(3) y
Cl2 C31 Cl1 110.64(19) y
Cl3 C32 Cl4 111.4(2) y
Cl5 C33 Cl6 111.9(3) y
C31 Cl1 Pd1 109.95(13) y
C4 N1 C5 111.3(2) y
C4 N1 C7 125.2(2) y
C5 N1 C7 123.4(2) y
C4 N2 C6 111.4(2) y
C4 N2 C19 124.2(2) y
C6 N2 C19 124.3(2) y
F4 P1 F6 89.91(13) y
F4 P1 F5 90.42(13) y
F6 P1 F5 90.08(13) y
F4 P1 F2 90.45(13) y
F6 P1 F2 90.01(12) y
F5 P1 F2 179.12(14) y
F4 P1 F3 90.74(14) y
F6 P1 F3 179.30(15) y
F5 P1 F3 90.20(14) y
F2 P1 F3 89.69(13) y
F4 P1 F1 179.60(15) y
F6 P1 F1 89.69(13) y
F5 P1 F1 89.54(13) y
F2 P1 F1 89.58(13) y
F3 P1 F1 89.67(14) y
C4 Pd1 C1 96.23(13) y
C4 Pd1 C2A 127.76(16) y
C1 Pd1 C2A 36.89(17) y
C4 Pd1 C3 164.28(13) y
C1 Pd1 C3 68.09(15) y
C2A Pd1 C3 37.39(17) y
C4 Pd1 Cl1 95.28(8) y
C1 Pd1 Cl1 167.08(10) y
C2A Pd1 Cl1 134.70(14) y
C3 Pd1 Cl1 100.43(11) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2A 1.342(6) y
C1 Pd1 2.082(3) y
C2A C3 1.401(6) y
C2A Pd1 2.154(4) y
C3 Pd1 2.213(4) y
C4 N1 1.359(4) y
C4 N2 1.363(4) y
C4 Pd1 2.050(3) y
C5 C6 1.346(4) y
C5 N1 1.383(4) y
C6 N2 1.390(4) y
C7 C12 1.398(4) y
C7 C8 1.404(4) y
C7 N1 1.449(4) y
C8 C9 1.398(4) y
C8 C13 1.523(4) y
C9 C10 1.387(5) y
C10 C11 1.390(5) y
C11 C12 1.395(4) y
C12 C16 1.522(4) y
C13 C15 1.529(5) y
C13 C14 1.536(4) y
C16 C17 1.531(5) y
C16 C18 1.538(5) y
C19 C20 1.404(4) y
C19 C24 1.409(4) y
C19 N2 1.446(4) y
C20 C21 1.396(4) y
C20 C25 1.527(5) y
C21 C22 1.382(5) y
C22 C23 1.389(5) y
C23 C24 1.393(4) y
C24 C28 1.519(4) y
C25 C27 1.530(5) y
C25 C26 1.537(5) y
C28 C29 1.529(5) y
C28 C30 1.544(5) y
C31 Cl2 1.753(4) y
C31 Cl1 1.787(3) y
C32 Cl3 1.756(4) y
C32 Cl4 1.762(4) y
C33 Cl5 1.751(5) y
C33 Cl6 1.767(5) y
Cl1 Pd1 2.4294(8) y
F1 P1 1.613(2) y
F2 P1 1.607(2) y
F3 P1 1.607(2) y
F4 P1 1.597(2) y
F5 P1 1.604(2) y
F6 P1 1.600(2) y
