#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:30:25 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178568 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/77/4067719.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_4067719
loop_
_publ_author_name
'Huynh, Han Vinh'
'Yeo, Chun Hui'
'Chew, Ying Xia'
_publ_section_title
;
 Syntheses, Structures, and Catalytic Activities of Hemilabile
 Thioether-Functionalized NHC Complexes
;
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1479
_journal_paper_doi               10.1021/om9010966
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C32 H32 Br2 N4 Pd S2'
_chemical_formula_weight         802.96
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.8510(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.2210(9)
_cell_length_b                   12.7785(8)
_cell_length_c                   17.3098(11)
_cell_measurement_reflns_used    2402
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      23.49
_cell_measurement_theta_min      2.50
_cell_volume                     3166.7(3)
_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      223(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11082
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    3.270
_exptl_absorpt_correction_T_max  0.7799
_exptl_absorpt_correction_T_min  0.5331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.275
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0450
_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)+(0.0663P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                2807
_reflns_number_total             3637
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om9010966_si_002.cif
_cod_data_source_block           cis-8a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 

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      C2/c
_cod_database_code               4067719
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Pd1 Pd 0.0000 0.59640(3) 0.2500 0.04027(14) Uani 1 2 d S
S1 S -0.06897(8) 0.75927(9) 0.52287(7) 0.0555(3) Uani 1 1 d .
N1 N 0.1702(2) 0.7227(2) 0.27523(19) 0.0404(7) Uani 1 1 d .
N2 N 0.1148(2) 0.7580(2) 0.37223(19) 0.0392(7) Uani 1 1 d .
Br1 Br 0.11069(3) 0.46492(3) 0.33287(3) 0.05886(17) Uani 1 1 d .
C1 C 0.0986(2) 0.7003(3) 0.3021(2) 0.0404(8) Uani 1 1 d .
C2 C 0.2308(2) 0.7936(3) 0.3264(2) 0.0407(8) Uani 1 1 d .
C3 C 0.3136(3) 0.8390(3) 0.3234(3) 0.0462(9) Uani 1 1 d .
H3 H 0.3380 0.8224 0.2817 0.055 Uiso 1 1 calc R
C4 C 0.3571(3) 0.9088(3) 0.3847(3) 0.0560(11) Uani 1 1 d .
H4 H 0.4123 0.9414 0.3844 0.067 Uiso 1 1 calc R
C5 C 0.3226(3) 0.9333(3) 0.4475(3) 0.0537(10) Uani 1 1 d .
H5 H 0.3544 0.9822 0.4879 0.064 Uiso 1 1 calc R
C6 C 0.2415(3) 0.8860(3) 0.4511(3) 0.0492(10) Uani 1 1 d .
H6 H 0.2184 0.9005 0.4940 0.059 Uiso 1 1 calc R
C7 C 0.1963(2) 0.8167(3) 0.3886(2) 0.0414(8) Uani 1 1 d .
C8 C 0.1852(3) 0.6726(4) 0.2049(3) 0.0520(10) Uani 1 1 d .
H8A H 0.1323 0.6281 0.1770 0.078 Uiso 1 1 calc R
H8B H 0.2416 0.6305 0.2237 0.078 Uiso 1 1 calc R
H8C H 0.1918 0.7258 0.1673 0.078 Uiso 1 1 calc R
C9 C 0.0546(3) 0.7582(3) 0.4217(2) 0.0433(9) Uani 1 1 d .
H9A H 0.0937 0.7566 0.4798 0.052 Uiso 1 1 calc R
H9B H 0.0169 0.6942 0.4101 0.052 Uiso 1 1 calc R
C10 C -0.0099(2) 0.8513(3) 0.4073(2) 0.0407(8) Uani 1 1 d .
C11 C -0.0107(3) 0.9287(3) 0.3513(2) 0.0458(9) Uani 1 1 d .
H11 H 0.0312 0.9244 0.3222 0.055 Uiso 1 1 calc R
C12 C -0.0716(3) 1.0120(4) 0.3373(3) 0.0594(11) Uani 1 1 d .
H12 H -0.0709 1.0642 0.2993 0.071 Uiso 1 1 calc R
C13 C -0.1331(3) 1.0178(4) 0.3794(3) 0.0651(13) Uani 1 1 d .
H13 H -0.1757 1.0737 0.3695 0.078 Uiso 1 1 calc R
C14 C -0.1330(3) 0.9424(4) 0.4362(3) 0.0580(11) Uani 1 1 d .
H14 H -0.1751 0.9481 0.4650 0.070 Uiso 1 1 calc R
C15 C -0.0723(3) 0.8586(3) 0.4517(2) 0.0434(8) Uani 1 1 d .
C16 C -0.1416(4) 0.8103(4) 0.5774(4) 0.0767(15) Uani 1 1 d .
H16A H -0.1219 0.8809 0.5959 0.115 Uiso 1 1 calc R
H16B H -0.1358 0.7662 0.6245 0.115 Uiso 1 1 calc R
H16C H -0.2062 0.8113 0.5412 0.115 Uiso 1 1 calc R
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 C1 95.6(2) . 2
C1 Pd1 Br1 85.96(10) . .
C1 Pd1 Br1 170.40(10) 2 .
C1 Pd1 Br1 170.40(10) . 2
C1 Pd1 Br1 85.96(10) 2 2
Br1 Pd1 Br1 94.07(3) . 2
C15 S1 C16 103.3(2) . .
C1 N1 C2 111.1(3) . .
C1 N1 C8 124.5(3) . .
C2 N1 C8 124.3(3) . .
C1 N2 C7 110.5(3) . .
C1 N2 C9 124.4(3) . .
C7 N2 C9 125.2(3) . .
N1 C1 N2 105.5(3) . .
N1 C1 Pd1 124.1(3) . .
N2 C1 Pd1 130.3(3) . .
N1 C2 C7 107.0(3) . .
N1 C2 C3 131.4(3) . .
C7 C2 C3 121.6(4) . .
C4 C3 C2 116.3(4) . .
C3 C4 C5 122.6(4) . .
C4 C5 C6 120.8(4) . .
C7 C6 C5 116.9(4) . .
C2 C7 C6 121.8(3) . .
C2 C7 N2 106.0(3) . .
C6 C7 N2 132.3(4) . .
N2 C9 C10 114.2(3) . .
C11 C10 C15 119.1(3) . .
C11 C10 C9 122.1(3) . .
C15 C10 C9 118.8(3) . .
C12 C11 C10 121.5(4) . .
C13 C12 C11 119.2(4) . .
C12 C13 C14 120.4(4) . .
C13 C14 C15 121.5(4) . .
C14 C15 C10 118.3(4) . .
C14 C15 S1 123.7(3) . .
C10 C15 S1 118.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 1.977(4) .
Pd1 C1 1.977(4) 2
Pd1 Br1 2.4652(5) .
Pd1 Br1 2.4653(5) 2
S1 C15 1.758(4) .
S1 C16 1.802(4) .
N1 C1 1.354(4) .
N1 C2 1.379(5) .
N1 C8 1.460(5) .
N2 C1 1.368(5) .
N2 C7 1.394(5) .
N2 C9 1.451(4) .
C2 C7 1.381(5) .
C2 C3 1.404(5) .
C3 C4 1.373(6) .
C4 C5 1.393(6) .
C5 C6 1.395(6) .
C6 C7 1.387(6) .
C9 C10 1.509(5) .
C10 C11 1.381(5) .
C10 C15 1.412(5) .
C11 C12 1.377(6) .
C12 C13 1.371(6) .
C13 C14 1.375(6) .
C14 C15 1.380(6) .
