#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:30:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178716 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/27/4082705.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_4082705
loop_
_publ_author_name
'Bernhammer, Jan C.'
'Huynh, Han Vinh'
_publ_section_title
;
 Benzimidazolin-2-ylidene Complexes of Palladium(II) Featuring a Thioether
 Moiety: Synthesis, Characterization, Molecular Dynamics, and Catalytic
 Activities
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              1266
_journal_paper_doi               10.1021/om500083r
_journal_volume                  33
_journal_year                    2014
_chemical_formula_sum            'C64 H68 Br4 N4 Pd2 S2'
_chemical_formula_weight         1489.78
_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                91.2520(10)
_cell_angle_beta                 94.0830(10)
_cell_angle_gamma                101.6050(10)
_cell_formula_units_Z            1
_cell_length_a                   8.9485(4)
_cell_length_b                   11.9417(6)
_cell_length_c                   14.7246(7)
_cell_measurement_reflns_used    5644
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.27
_cell_volume                     1536.34(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20080
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    3.296
_exptl_absorpt_correction_T_max  0.5629
_exptl_absorpt_correction_T_min  0.4603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.828
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         7047
_refine_ls_number_restraints     152
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0344P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0738
_reflns_number_gt                5974
_reflns_number_total             7047
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om500083r_si_002.cif
_cod_data_source_block           c807
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not measured' 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_original_sg_symbol_H-M      P-1
_cod_database_code               4082705
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 0.38708(2) 0.077221(16) 0.360016(12) 0.01170(6) Uani 1 1 d . . .
Br1 Br 0.36201(3) 0.22676(2) 0.469149(17) 0.01794(7) Uani 1 1 d . . .
Br2 Br 0.44270(3) -0.06986(2) 0.25985(2) 0.02502(8) Uani 1 1 d . . .
S1 S 0.85547(7) 0.02978(5) 0.60603(4) 0.01391(13) Uani 1 1 d . . .
N1 N 0.7243(2) 0.15733(18) 0.36846(14) 0.0140(4) Uani 1 1 d . . .
N2 N 0.6083(2) 0.25114(18) 0.27050(14) 0.0144(4) Uani 1 1 d . . .
C1 C 0.5858(3) 0.1686(2) 0.33251(16) 0.0139(5) Uani 1 1 d . . .
C2 C 0.8388(3) 0.2334(2) 0.32932(17) 0.0142(5) Uani 1 1 d . . .
C3 C 0.9976(3) 0.2525(2) 0.34369(18) 0.0172(5) Uani 1 1 d . . .
H3 H 1.0469 0.2116 0.3872 0.021 Uiso 1 1 calc R . .
C4 C 1.0791(3) 0.3337(2) 0.29147(19) 0.0217(6) Uani 1 1 d . . .
H4 H 1.1877 0.3502 0.2997 0.026 Uiso 1 1 calc R . .
C5 C 1.0068(3) 0.3926(2) 0.22678(19) 0.0243(6) Uani 1 1 d . . .
H5 H 1.0677 0.4467 0.1912 0.029 Uiso 1 1 calc R . .
C6 C 0.8496(3) 0.3748(2) 0.21284(18) 0.0207(6) Uani 1 1 d . . .
H6 H 0.8009 0.4160 0.1693 0.025 Uiso 1 1 calc R . .
C7 C 0.7655(3) 0.2932(2) 0.26597(17) 0.0156(5) Uani 1 1 d . . .
C8 C 0.7527(3) 0.0755(2) 0.43613(17) 0.0150(5) Uani 1 1 d . . .
H8A H 0.8341 0.0370 0.4171 0.018 Uiso 1 1 calc R . .
H8B H 0.6586 0.0164 0.4400 0.018 Uiso 1 1 calc R . .
C9 C 0.8012(3) 0.1345(2) 0.52962(17) 0.0165(5) Uani 1 1 d . . .
H9A H 0.7155 0.1648 0.5529 0.020 Uiso 1 1 calc R . .
H9B H 0.8888 0.1992 0.5252 0.020 Uiso 1 1 calc R . .
C10 C 0.9454(3) 0.1210(2) 0.70473(18) 0.0209(6) Uani 1 1 d . . .
H10 H 0.8772 0.1739 0.7212 0.025 Uiso 1 1 calc R . .
C11 C 0.9613(4) 0.0416(3) 0.78332(19) 0.0313(7) Uani 1 1 d . . .
H11A H 1.0241 -0.0129 0.7663 0.047 Uiso 1 1 calc R . .
H11B H 0.8597 -0.0003 0.7965 0.047 Uiso 1 1 calc R . .
H11C H 1.0103 0.0870 0.8376 0.047 Uiso 1 1 calc R . .
C12 C 1.0993(3) 0.1907(3) 0.6839(2) 0.0291(7) Uani 1 1 d . . .
H12A H 1.1374 0.2477 0.7334 0.044 Uiso 1 1 calc R . .
H12B H 1.0882 0.2296 0.6267 0.044 Uiso 1 1 calc R . .
H12C H 1.1720 0.1400 0.6783 0.044 Uiso 1 1 calc R . .
C13 C 0.4785(3) 0.2855(2) 0.21750(17) 0.0159(5) Uani 1 1 d . . .
H13 H 0.3875 0.2611 0.2533 0.019 Uiso 1 1 calc R . .
C14 C 0.4386(3) 0.2223(2) 0.12569(17) 0.0160(5) Uani 1 1 d . . .
C15 C 0.2855(3) 0.1938(3) 0.09394(19) 0.0257(6) Uani 1 1 d . . .
H15 H 0.2097 0.2130 0.1300 0.031 Uiso 1 1 calc R . .
C16 C 0.2423(4) 0.1374(3) 0.0097(2) 0.0306(7) Uani 1 1 d . . .
H16 H 0.1371 0.1172 -0.0111 0.037 Uiso 1 1 calc R . .
C17 C 0.3512(4) 0.1108(2) -0.04343(19) 0.0275(7) Uani 1 1 d . . .
H17 H 0.3215 0.0728 -0.1012 0.033 Uiso 1 1 calc R . .
C18 C 0.5037(3) 0.1394(2) -0.01271(19) 0.0252(6) Uani 1 1 d . . .
H18 H 0.5790 0.1213 -0.0496 0.030 Uiso 1 1 calc R . .
C19 C 0.5478(3) 0.1944(2) 0.07172(18) 0.0192(6) Uani 1 1 d . . .
H19 H 0.6530 0.2130 0.0927 0.023 Uiso 1 1 calc R . .
C20 C 0.5022(3) 0.4147(2) 0.21395(18) 0.0178(6) Uani 1 1 d . . .
C21 C 0.5235(4) 0.4722(2) 0.1333(2) 0.0323(8) Uani 1 1 d . . .
H21 H 0.5234 0.4299 0.0779 0.039 Uiso 1 1 calc R . .
C22 C 0.5449(4) 0.5902(3) 0.1327(2) 0.0411(9) Uani 1 1 d . . .
H22 H 0.5606 0.6283 0.0771 0.049 Uiso 1 1 calc R . .
C23 C 0.5434(4) 0.6525(3) 0.2121(2) 0.0306(7) Uani 1 1 d . . .
H23 H 0.5571 0.7334 0.2114 0.037 Uiso 1 1 calc R . .
C24 C 0.5220(3) 0.5973(3) 0.2925(2) 0.0305(7) Uani 1 1 d . . .
H24 H 0.5212 0.6401 0.3476 0.037 Uiso 1 1 calc R . .
C25 C 0.5016(3) 0.4791(2) 0.29331(19) 0.0239(6) Uani 1 1 d . . .
H25 H 0.4869 0.4417 0.3492 0.029 Uiso 1 1 calc R . .
C1W C 0.7388(6) 0.4476(8) 0.5126(6) 0.0451(19) Uani 0.50 1 d PDU A -1
H1WA H 0.7247 0.4179 0.5736 0.068 Uiso 0.50 1 calc PR A -1
H1WB H 0.6910 0.3881 0.4667 0.068 Uiso 0.50 1 calc PR A -1
H1WC H 0.6911 0.5143 0.5057 0.068 Uiso 0.50 1 calc PR A -1
C2W C 0.9054(4) 0.4818(5) 0.5001(3) 0.0317(11) Uani 0.50 1 d PGDU A -1
C3W C 1.0119(5) 0.4557(4) 0.5654(3) 0.0347(14) Uani 0.50 1 d PGDU A -1
H3W H 0.9785 0.4158 0.6178 0.042 Uiso 0.50 1 calc PR A -1
C4W C 1.1674(5) 0.4878(4) 0.5540(3) 0.0422(14) Uani 0.50 1 d PGDU A -1
H4W H 1.2402 0.4699 0.5986 0.051 Uiso 0.50 1 calc PR A -1
C5W C 1.2163(4) 0.5460(5) 0.4773(4) 0.0439(16) Uani 0.50 1 d PGDU A -1
H5W H 1.3226 0.5680 0.4695 0.053 Uiso 0.50 1 calc PR A -1
C6W C 1.1098(6) 0.5722(4) 0.4121(3) 0.0425(14) Uani 0.50 1 d PGDU A -1
H6W H 1.1432 0.6120 0.3597 0.051 Uiso 0.50 1 calc PR A -1
C7W C 0.9543(5) 0.5401(4) 0.4235(3) 0.0356(14) Uani 0.50 1 d PGDU A -1
H7W H 0.8815 0.5580 0.3789 0.043 Uiso 0.50 1 calc PR A -1
C1X C 1.0680(12) 0.6644(7) 1.0629(7) 0.071(3) Uani 0.50 1 d PDU B -1
H1XA H 1.1653 0.6669 1.0987 0.106 Uiso 0.50 1 calc PR B -1
H1XB H 0.9901 0.6763 1.1035 0.106 Uiso 0.50 1 calc PR B -1
H1XC H 1.0813 0.7248 1.0184 0.106 Uiso 0.50 1 calc PR B -1
C2X C 1.0182(6) 0.5501(4) 1.0138(4) 0.0445(13) Uani 0.50 1 d PGDU B -1
C3X C 1.1269(5) 0.4856(5) 0.9965(4) 0.0447(15) Uani 0.50 1 d PGDU B -1
H3X H 1.2318 0.5145 1.0149 0.054 Uiso 0.50 1 calc PR B -1
C4X C 1.0822(6) 0.3789(5) 0.9520(4) 0.0502(14) Uani 0.50 1 d PGDU B -1
H4X H 1.1565 0.3349 0.9402 0.060 Uiso 0.50 1 calc PR B -1
C5X C 0.9288(6) 0.3367(4) 0.9250(4) 0.0559(18) Uani 0.50 1 d PGDU B -1
H5X H 0.8983 0.2638 0.8946 0.067 Uiso 0.50 1 calc PR B -1
C6X C 0.8201(5) 0.4012(5) 0.9423(4) 0.0506(15) Uani 0.50 1 d PGDU B -1
H6X H 0.7153 0.3723 0.9238 0.061 Uiso 0.50 1 calc PR B -1
C7X C 0.8648(6) 0.5078(5) 0.9868(4) 0.0440(15) Uani 0.50 1 d PGDU B -1
H7X H 0.7905 0.5519 0.9986 0.053 Uiso 0.50 1 calc PR B -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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C1 Pd1 S1 178.78(7) . 2_656
C1 Pd1 Br2 86.31(7) . .
S1 Pd1 Br2 94.783(18) 2_656 .
C1 Pd1 Br1 89.08(7) . .
S1 Pd1 Br1 89.880(18) 2_656 .
Br2 Pd1 Br1 173.132(12) . .
C9 S1 C10 101.42(12) . .
C9 S1 Pd1 101.86(9) . 2_656
C10 S1 Pd1 110.20(9) . 2_656
C1 N1 C2 110.1(2) . .
C1 N1 C8 125.6(2) . .
C2 N1 C8 124.3(2) . .
C1 N2 C7 109.9(2) . .
C1 N2 C13 121.7(2) . .
C7 N2 C13 128.4(2) . .
N1 C1 N2 107.5(2) . .
N1 C1 Pd1 126.54(18) . .
N2 C1 Pd1 125.91(18) . .
N1 C2 C3 131.1(2) . .
N1 C2 C7 106.6(2) . .
C3 C2 C7 122.2(2) . .
C4 C3 C2 116.3(2) . .
C3 C4 C5 121.8(2) . .
C6 C5 C4 122.1(3) . .
C5 C6 C7 116.6(2) . .
C2 C7 C6 120.9(2) . .
C2 C7 N2 105.9(2) . .
C6 C7 N2 133.2(2) . .
N1 C8 C9 111.1(2) . .
C8 C9 S1 108.01(17) . .
C12 C10 C11 111.5(2) . .
C12 C10 S1 110.9(2) . .
C11 C10 S1 106.76(19) . .
N2 C13 C14 113.0(2) . .
N2 C13 C20 110.9(2) . .
C14 C13 C20 114.7(2) . .
C15 C14 C19 119.0(2) . .
C15 C14 C13 117.9(2) . .
C19 C14 C13 123.2(2) . .
C14 C15 C16 120.4(3) . .
C17 C16 C15 120.2(3) . .
C16 C17 C18 119.8(3) . .
C17 C18 C19 120.5(3) . .
C18 C19 C14 120.2(3) . .
C25 C20 C21 118.0(3) . .
C25 C20 C13 119.6(2) . .
C21 C20 C13 122.5(2) . .
C22 C21 C20 120.9(3) . .
C23 C22 C21 120.2(3) . .
C24 C23 C22 119.8(3) . .
C23 C24 C25 120.0(3) . .
C20 C25 C24 121.1(3) . .
C3W C2W C7W 120.0 . .
C3W C2W C1W 119.9(5) . .
C7W C2W C1W 120.1(5) . .
C2W C3W C4W 120.0 . .
C3W C4W C5W 120.0 . .
C6W C5W C4W 120.0 . .
C5W C6W C7W 120.0 . .
C6W C7W C2W 120.0 . .
C3X C2X C7X 120.0 . .
C3X C2X C1X 119.4(6) . .
C7X C2X C1X 120.6(6) . .
C2X C3X C4X 120.0 . .
C3X C4X C5X 120.0 . .
C6X C5X C4X 120.0 . .
C7X C6X C5X 120.0 . .
C6X C7X C2X 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 1.964(2) .
Pd1 S1 2.3791(6) 2_656
Pd1 Br2 2.4189(3) .
Pd1 Br1 2.4307(3) .
S1 C9 1.815(3) .
S1 C10 1.832(3) .
S1 Pd1 2.3791(6) 2_656
N1 C1 1.346(3) .
N1 C2 1.393(3) .
N1 C8 1.456(3) .
N2 C1 1.353(3) .
N2 C7 1.402(3) .
N2 C13 1.484(3) .
C2 C3 1.393(3) .
C2 C7 1.394(3) .
C3 C4 1.376(4) .
C4 C5 1.395(4) .
C5 C6 1.380(4) .
C6 C7 1.396(3) .
C8 C9 1.526(3) .
C10 C12 1.514(4) .
C10 C11 1.529(4) .
C13 C14 1.517(3) .
C13 C20 1.518(4) .
C14 C15 1.388(4) .
C14 C19 1.389(4) .
C15 C16 1.389(4) .
C16 C17 1.373(4) .
C17 C18 1.379(4) .
C18 C19 1.387(4) .
C20 C25 1.386(4) .
C20 C21 1.390(4) .
C21 C22 1.383(4) .
C22 C23 1.375(4) .
C23 C24 1.375(4) .
C24 C25 1.386(4) .
C1W C2W 1.490(4) .
C2W C3W 1.3900 .
C2W C7W 1.3900 .
C3W C4W 1.3900 .
C4W C5W 1.3900 .
C5W C6W 1.3900 .
C6W C7W 1.3900 .
C1X C2X 1.500(4) .
C2X C3X 1.3900 .
C2X C7X 1.3900 .
C3X C4X 1.3900 .
C4X C5X 1.3900 .
C5X C6X 1.3900 .
C6X C7X 1.3900 .
