#------------------------------------------------------------------------------
#$Date: 2016-03-24 17:20:36 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179686 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/08/7000877.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_7000877
loop_
_publ_author_name
'Fliedel, Christophe'
'Schnee, Gilles'
'Braunstein, Pierre'
_publ_section_title
;
 Versatile coordination modes of novel hemilabile S-NHC ligands
;
_journal_issue                   14
_journal_name_full               'Dalton Transactions'
_journal_page_first              2474
_journal_page_last               2476
_journal_paper_doi               10.1039/b902314n
_journal_year                    2009
_chemical_formula_sum            'C29 H35 Cl2 N2 P Pd S'
_chemical_formula_weight         651.92
_chemical_name_common            'Compound X'
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2008-09-30T17:09:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 133.128(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8722(6)
_cell_length_b                   17.6615(5)
_cell_length_c                   18.3472(6)
_cell_measurement_reflns_used    15176
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     3044.2(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.0243255
_diffrn_orient_matrix_UB_12      0.0536066
_diffrn_orient_matrix_UB_13      0.0061789
_diffrn_orient_matrix_UB_21      -0.0487208
_diffrn_orient_matrix_UB_22      0.0083023
_diffrn_orient_matrix_UB_23      0.0559706
_diffrn_orient_matrix_UB_31      0.0554387
_diffrn_orient_matrix_UB_32      -0.0162254
_diffrn_orient_matrix_UB_33      0.0490534
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16443
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.245
_refine_diff_density_min         -1.11
_refine_diff_density_rms         0.26
_refine_ls_extinction_coef       0.0092(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.1
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5669
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.083
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1119P)²+4.9714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1665
_refine_ls_wR_factor_ref         0.1874
_reflns_number_gt                4361
_reflns_number_total             5669
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b902314n.txt
_cod_data_source_block           Complex8
_cod_original_cell_volume        3044.18(22)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7000877
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Pd1 Pd 1.05257(4) 0.68705(2) 1.14164(3) 0.0247(2) Uani 1 1 d . . .
P1 P 0.89423(16) 0.78300(8) 1.06649(11) 0.0275(4) Uani 1 1 d . . .
Cl1 Cl 1.09210(16) 0.70195(9) 1.28655(10) 0.0329(4) Uani 1 1 d . . .
Cl2 Cl 1.22163(16) 0.58866(8) 1.21404(11) 0.0381(4) Uani 1 1 d . . .
N1 N 0.9250(5) 0.6085(3) 0.9535(4) 0.0331(11) Uani 1 1 d . . .
N2 N 1.0639(6) 0.6970(3) 0.9827(4) 0.0341(12) Uani 1 1 d . . .
S1 S 1.4353(3) 0.81665(16) 1.1522(2) 0.0895(9) Uani 1 1 d . . .
C1 C 0.8566(7) 0.8241(3) 0.9598(5) 0.0338(14) Uani 1 1 d . . .
C2 C 0.7740(7) 0.7848(4) 0.8695(5) 0.0382(15) Uani 1 1 d . . .
H2 H 0.7261 0.7401 0.8614 0.046 Uiso 1 1 calc R . .
C3 C 0.7601(8) 0.8090(4) 0.7918(5) 0.0443(17) Uani 1 1 d . . .
H3 H 0.7027 0.7817 0.7307 0.053 Uiso 1 1 calc R . .
C4 C 0.8305(8) 0.8734(4) 0.8041(5) 0.0524(19) Uani 1 1 d . . .
H4 H 0.8236 0.8899 0.7516 0.063 Uiso 1 1 calc R . .
C5 C 0.9109(10) 0.9143(4) 0.8913(6) 0.060(2) Uani 1 1 d . . .
H5 H 0.958 0.9591 0.8986 0.072 Uiso 1 1 calc R . .
C6 C 0.9230(8) 0.8899(4) 0.9691(5) 0.0484(18) Uani 1 1 d . . .
H6 H 0.9774 0.9186 1.0289 0.058 Uiso 1 1 calc R . .
C7 C 0.9511(7) 0.8645(3) 1.1470(5) 0.0355(14) Uani 1 1 d . . .
C8 C 1.0938(8) 0.8797(4) 1.2242(5) 0.0435(16) Uani 1 1 d . . .
H8 H 1.163 0.8465 1.2373 0.052 Uiso 1 1 calc R . .
C9 C 1.1363(10) 0.9438(4) 1.2828(6) 0.057(2) Uani 1 1 d . . .
H9 H 1.2347 0.9541 1.3366 0.068 Uiso 1 1 calc R . .
C10 C 1.0357(12) 0.9920(4) 1.2629(7) 0.061(2) Uani 1 1 d . . .
H10 H 1.0653 1.0356 1.3034 0.073 Uiso 1 1 calc R . .
C11 C 0.8958(11) 0.9785(4) 1.1866(7) 0.059(2) Uani 1 1 d . . .
H11 H 0.8278 1.013 1.173 0.071 Uiso 1 1 calc R . .
C12 C 0.8505(9) 0.9146(4) 1.1279(6) 0.0497(18) Uani 1 1 d . . .
H12 H 0.7517 0.9048 1.0749 0.06 Uiso 1 1 calc R . .
C13 C 0.7224(6) 0.7547(4) 1.0195(4) 0.0346(14) Uani 1 1 d . . .
C14 C 0.5941(7) 0.7899(4) 0.9371(5) 0.0491(18) Uani 1 1 d . . .
H14 H 0.5954 0.8299 0.9031 0.059 Uiso 1 1 calc R . .
C15 C 0.4667(8) 0.7663(5) 0.9056(6) 0.059(2) Uani 1 1 d . . .
H15 H 0.3813 0.7916 0.8513 0.07 Uiso 1 1 calc R . .
C16 C 0.4610(8) 0.7084(5) 0.9501(5) 0.0515(18) Uani 1 1 d U . .
H16 H 0.3717 0.692 0.9257 0.062 Uiso 1 1 calc R . .
C17 C 0.5838(7) 0.6727(4) 1.0308(5) 0.0474(17) Uani 1 1 d . . .
H17 H 0.5794 0.6326 1.0632 0.057 Uiso 1 1 calc R . .
C18 C 0.7152(7) 0.6951(4) 1.0652(5) 0.0383(15) Uani 1 1 d . . .
H18 H 0.7997 0.6695 1.12 0.046 Uiso 1 1 calc R . .
C19 C 1.0112(6) 0.6645(3) 1.0183(4) 0.0308(13) Uani 1 1 d . . .
C20 C 0.9257(7) 0.6054(4) 0.8787(5) 0.0382(15) Uani 1 1 d . . .
H20 H 0.8748 0.5704 0.8248 0.046 Uiso 1 1 calc R . .
C21 C 1.0116(8) 0.6609(4) 0.8962(5) 0.0400(15) Uani 1 1 d . . .
H21 H 1.0325 0.673 0.857 0.048 Uiso 1 1 calc R . .
C22 C 0.8469(8) 0.5552(4) 0.9639(6) 0.0554(14) Uani 1 1 d U . .
H22A H 0.8827 0.5611 1.0315 0.066 Uiso 1 1 calc R . .
H22B H 0.8685 0.5028 0.9585 0.066 Uiso 1 1 calc R . .
C23 C 0.6895(8) 0.5654(4) 0.8890(6) 0.0623(13) Uani 1 1 d DU . .
H23A H 0.6524 0.5577 0.8213 0.075 Uiso 1 1 calc R . .
H23B H 0.6671 0.618 0.893 0.075 Uiso 1 1 calc R . .
C24 C 0.6124(7) 0.5088(5) 0.9055(6) 0.0705(15) Uani 1 1 d DU . .
H24A H 0.6488 0.4567 0.9158 0.085 Uiso 1 1 calc R . .
H24B H 0.629 0.5237 0.9647 0.085 Uiso 1 1 calc R . .
C25 C 0.4543(8) 0.5125(6) 0.8116(7) 0.103(3) Uani 1 1 d DU . .
H25A H 0.425 0.5656 0.7933 0.155 Uiso 1 1 calc R . .
H25B H 0.3997 0.488 0.8243 0.155 Uiso 1 1 calc R . .
H25C H 0.4366 0.4864 0.7569 0.155 Uiso 1 1 calc R . .
C26 C 1.1628(7) 0.7599(4) 1.0289(6) 0.0497(14) Uani 1 1 d U . .
H26A H 1.157 0.787 1.0733 0.06 Uiso 1 1 calc R A .
H26B H 1.1333 0.7957 0.9761 0.06 Uiso 1 1 calc R . .
C27 C 1.3146(8) 0.7371(4) 1.0886(6) 0.0552(14) Uani 1 1 d U . .
H27A H 1.3225 0.7139 1.0434 0.066 Uiso 1 1 calc R . .
H27B H 1.3426 0.6986 1.1385 0.066 Uiso 1 1 calc R . .
C29 C 1.5007(15) 0.9225(8) 1.0852(11) 0.134(4) Uani 1 1 d U A 1
H29A H 1.5248 0.9567 1.1369 0.201 Uiso 1 1 calc R A 1
H29B H 1.4742 0.9523 1.0295 0.201 Uiso 1 1 calc R A 1
H29C H 1.5833 0.8908 1.1131 0.201 Uiso 1 1 calc R A 1
C28 C 1.3823(14) 0.8747(8) 1.0496(10) 0.124(4) Uani 1 1 d U A 1
H28A H 1.3541 0.8419 0.9948 0.149 Uiso 1 1 calc R A 1
H28B H 1.2996 0.9065 1.0235 0.149 Uiso 1 1 calc R A 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Pd Pd -0.9988 1.0072 '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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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
C19 Pd1 P1 91.62(17) . . ?
C19 Pd1 Cl1 174.25(18) . . ?
P1 Pd1 Cl1 90.78(5) . . ?
C19 Pd1 Cl2 85.35(17) . . ?
P1 Pd1 Cl2 176.32(6) . . ?
Cl1 Pd1 Cl2 92.43(5) . . ?
C13 P1 C1 105.0(3) . . ?
C13 P1 C7 106.7(3) . . ?
C1 P1 C7 102.8(3) . . ?
C13 P1 Pd1 112.5(2) . . ?
C1 P1 Pd1 115.0(2) . . ?
C7 P1 Pd1 113.8(2) . . ?
C19 N1 C20 110.2(5) . . ?
C19 N1 C22 124.9(5) . . ?
C20 N1 C22 124.8(5) . . ?
C19 N2 C21 110.3(5) . . ?
C19 N2 C26 125.1(5) . . ?
C21 N2 C26 124.6(6) . . ?
C27 S1 C28 102.8(5) . . ?
C6 C1 C2 118.0(6) . . ?
C6 C1 P1 121.1(5) . . ?
C2 C1 P1 120.4(5) . . ?
C3 C2 C1 121.9(6) . . ?
C3 C2 H2 119 . . ?
C1 C2 H2 119 . . ?
C4 C3 C2 118.9(7) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 120.9(7) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.9(7) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.5(6) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C12 119.3(6) . . ?
C8 C7 P1 120.2(5) . . ?
C12 C7 P1 120.4(5) . . ?
C7 C8 C9 119.8(7) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 119.9(8) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 120.9(7) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.4(7) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 119.6(8) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C18 C13 C14 118.0(6) . . ?
C18 C13 P1 119.1(5) . . ?
C14 C13 P1 122.9(5) . . ?
C15 C14 C13 120.1(7) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 121.3(7) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 120.3(7) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 120.1(7) . . ?
C16 C17 H17 120 . . ?
C18 C17 H17 120 . . ?
C13 C18 C17 120.1(6) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
N1 C19 N2 105.5(5) . . ?
N1 C19 Pd1 124.9(4) . . ?
N2 C19 Pd1 129.5(4) . . ?
C21 C20 N1 107.3(5) . . ?
C21 C20 H20 126.3 . . ?
N1 C20 H20 126.3 . . ?
C20 C21 N2 106.6(5) . . ?
C20 C21 H21 126.7 . . ?
N2 C21 H21 126.7 . . ?
N1 C22 C23 114.8(6) . . ?
N1 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
N1 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 C24 112.6(6) . . ?
C22 C23 H23A 109.1 . . ?
C24 C23 H23A 109.1 . . ?
C22 C23 H23B 109.1 . . ?
C24 C23 H23B 109.1 . . ?
H23A C23 H23B 107.8 . . ?
C25 C24 C23 106.6(7) . . ?
C25 C24 H24A 110.4 . . ?
C23 C24 H24A 110.4 . . ?
C25 C24 H24B 110.4 . . ?
C23 C24 H24B 110.4 . . ?
H24A C24 H24B 108.6 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N2 C26 C27 114.0(6) . . ?
N2 C26 H26A 108.8 . . ?
C27 C26 H26A 108.8 . . ?
N2 C26 H26B 108.8 . . ?
C27 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
C26 C27 S1 112.3(5) . . ?
C26 C27 H27A 109.2 . . ?
S1 C27 H27A 109.2 . . ?
C26 C27 H27B 109.2 . . ?
S1 C27 H27B 109.2 . . ?
H27A C27 H27B 107.9 . . ?
C29 C28 S1 109.1(10) . . ?
C29 C28 H28A 109.9 . . ?
S1 C28 H28A 109.9 . . ?
C29 C28 H28B 109.9 . . ?
S1 C28 H28B 109.9 . . ?
H28A C28 H28B 108.3 . . ?
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 C19 1.978(6) . ?
Pd1 P1 2.2549(15) . ?
Pd1 Cl1 2.3554(15) . ?
Pd1 Cl2 2.3596(15) . ?
P1 C13 1.811(6) . ?
P1 C1 1.816(6) . ?
P1 C7 1.821(6) . ?
N1 C19 1.350(7) . ?
N1 C20 1.379(8) . ?
N1 C22 1.482(8) . ?
N2 C19 1.350(8) . ?
N2 C21 1.385(8) . ?
N2 C26 1.448(9) . ?
S1 C27 1.808(8) . ?
S1 C28 1.818(12) . ?
C1 C6 1.382(9) . ?
C1 C2 1.397(9) . ?
C2 C3 1.377(9) . ?
C2 H2 0.95 . ?
C3 C4 1.373(10) . ?
C3 H3 0.95 . ?
C4 C5 1.375(10) . ?
C4 H4 0.95 . ?
C5 C6 1.393(10) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.376(9) . ?
C7 C12 1.400(9) . ?
C8 C9 1.389(10) . ?
C8 H8 0.95 . ?
C9 C10 1.375(12) . ?
C9 H9 0.95 . ?
C10 C11 1.347(12) . ?
C10 H10 0.95 . ?
C11 C12 1.383(10) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 C18 1.387(9) . ?
C13 C14 1.409(9) . ?
C14 C15 1.379(10) . ?
C14 H14 0.95 . ?
C15 C16 1.342(11) . ?
C15 H15 0.95 . ?
C16 C17 1.374(10) . ?
C16 H16 0.95 . ?
C17 C18 1.399(9) . ?
C17 H17 0.95 . ?
C18 H18 0.95 . ?
C20 C21 1.342(9) . ?
C20 H20 0.95 . ?
C21 H21 0.95 . ?
C22 C23 1.489(11) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 C24 1.577(15) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 C25 1.523(14) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
C26 C27 1.501(10) . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C27 H27A 0.99 . ?
C27 H27B 0.99 . ?
C29 C28 1.450(15) . ?
C29 H29A 0.98 . ?
C29 H29B 0.98 . ?
C29 H29C 0.98 . ?
C28 H28A 0.99 . ?
C28 H28B 0.99 . ?
