#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:02:18 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178690 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/01/4080101.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_4080101
loop_
_publ_author_name
'Sabater, Sara'
'Mata, Jose A.'
'Peris, Eduardo'
_publ_section_title
;
 Chiral Palladacycles with N-Heterocyclic Carbene Ligands as Catalysts for
 Asymmetric Hydrophosphination
;
_journal_issue                   4
_journal_name_full               Organometallics
_journal_page_first              1112
_journal_paper_doi               10.1021/om400007a
_journal_volume                  32
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H26 Cl2 N2 Pd'
_chemical_formula_sum            'C24 H26 Cl2 N2 Pd'
_chemical_formula_weight         519.77
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-01-23
_audit_creation_method
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.636(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   35.2455(18)
_cell_length_b                   6.7435(3)
_cell_length_c                   9.6250(6)
_cell_measurement_reflns_used    5916
_cell_measurement_temperature    199.95(10)
_cell_measurement_theta_max      29.2872
_cell_measurement_theta_min      2.8348
_cell_volume                     2232.2(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      199.95(10)
_diffrn_detector_area_resol_mean 10.4051
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_details
;
  1 omega  -97.00  -58.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.3126  178.0000 -180.0000 39

  2 omega  -75.00   12.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.3126  -57.0000  120.0000 87

  3 omega  -18.00   54.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9376 -101.0000   52.0000 72

  4 omega   49.00   74.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9376  178.0000  -60.0000 25

  5 omega  -64.00   38.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9376  -38.0000   90.0000 102

  6 omega  -20.00    9.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9376  -99.0000  -90.0000 29

  7 omega  -14.00   88.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9376   38.0000   90.0000 102
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0183324000
_diffrn_orient_matrix_UB_12      -0.0243393000
_diffrn_orient_matrix_UB_13      0.0144270000
_diffrn_orient_matrix_UB_21      0.0015165000
_diffrn_orient_matrix_UB_22      -0.0972426000
_diffrn_orient_matrix_UB_23      -0.0263623000
_diffrn_orient_matrix_UB_31      0.0093275000
_diffrn_orient_matrix_UB_32      -0.0317892000
_diffrn_orient_matrix_UB_33      0.0693127000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13643
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.35
_diffrn_reflns_theta_min         2.84
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.2415
_exptl_crystal_size_mid          0.1028
_exptl_crystal_size_min          0.0749
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         5264
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0282
_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)+(0.0231P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0538
_refine_ls_wR_factor_ref         0.0571
_reflns_number_gt                4980
_reflns_number_total             5264
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400007a_si_001.cif
_cod_data_source_block           compound_9_str1297shapes
_cod_database_code               4080101
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         'C24 H24 N2 Cl2 Pd2'
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -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
Pd1 Pd 0.495043(5) 0.55352(4) 0.162631(19) 0.01813(6) Uani 1 1 d .
Cl3 Cl 0.45459(2) 0.28069(10) 0.13477(9) 0.02493(18) Uani 1 1 d .
N5 N 0.44790(7) 0.7422(4) 0.1243(3) 0.0212(6) Uani 1 1 d .
H5A H 0.4568 0.8696 0.1186 0.025 Uiso 1 1 calc R
H5B H 0.4324 0.7111 0.0371 0.025 Uiso 1 1 calc R
C16 C 0.64431(7) 0.5588(6) 0.5190(3) 0.0275(6) Uani 1 1 d .
H16 H 0.6210 0.6333 0.5083 0.033 Uiso 1 1 calc R
C23 C 0.31332(8) 1.0424(7) 0.0863(3) 0.0352(7) Uani 1 1 d .
H23 H 0.2894 1.1106 0.0549 0.042 Uiso 1 1 calc R
C28 C 0.35996(7) 0.5707(6) 0.0072(3) 0.0265(6) Uani 1 1 d .
H28 H 0.3835 0.4991 0.0376 0.032 Uiso 1 1 calc R
C21 C 0.37740(8) 1.0250(5) 0.2358(3) 0.0290(7) Uani 1 1 d .
H21 H 0.3969 1.0844 0.3077 0.035 Uiso 1 1 calc R
C17 C 0.64379(8) 0.3764(4) 0.4434(3) 0.0216(6) Uani 1 1 d .
C11 C 0.68054(8) 0.0881(5) 0.3884(3) 0.0316(8) Uani 1 1 d .
H11 H 0.7040 0.0140 0.4029 0.038 Uiso 1 1 calc R
C20 C 0.38498(8) 0.8452(4) 0.1797(3) 0.0227(6) Uani 1 1 d .
C29 C 0.35536(8) 0.7566(5) 0.0703(3) 0.0229(6) Uani 1 1 d .
C19 C 0.42323(8) 0.7379(4) 0.2335(3) 0.0225(6) Uani 1 1 d .
H19 H 0.4172 0.5961 0.2501 0.027 Uiso 1 1 calc R
C22 C 0.34149(10) 1.1235(5) 0.1895(4) 0.0360(8) Uani 1 1 d .
H22 H 0.3370 1.2470 0.2308 0.043 Uiso 1 1 calc R
C8 C 0.61007(8) 0.2982(4) 0.3493(3) 0.0218(6) Uani 1 1 d .
C6 C 0.57107(8) 0.4014(4) 0.3387(3) 0.0213(6) Uani 1 1 d .
H6 H 0.5760 0.5473 0.3484 0.026 Uiso 1 1 calc R
C14 C 0.71231(8) 0.5215(6) 0.6241(3) 0.0356(9) Uani 1 1 d .
H14 H 0.7353 0.5708 0.6851 0.043 Uiso 1 1 calc R
C12 C 0.67959(8) 0.2683(5) 0.4624(3) 0.0268(7) Uani 1 1 d .
C9 C 0.61302(8) 0.1267(4) 0.2766(3) 0.0282(7) Uani 1 1 d .
H9 H 0.5908 0.0785 0.2109 0.034 Uiso 1 1 calc R
C13 C 0.71323(8) 0.3473(5) 0.5546(3) 0.0337(8) Uani 1 1 d .
H13 H 0.7370 0.2762 0.5679 0.040 Uiso 1 1 calc R
C10 C 0.64816(8) 0.0193(5) 0.2964(3) 0.0338(8) Uani 1 1 d .
H10 H 0.6493 -0.1007 0.2457 0.041 Uiso 1 1 calc R
C18 C 0.44817(8) 0.8188(5) 0.3711(3) 0.0300(7) Uani 1 1 d .
H18A H 0.4712 0.7348 0.4012 0.045 Uiso 1 1 calc R
H18B H 0.4331 0.8193 0.4453 0.045 Uiso 1 1 calc R
H18C H 0.4563 0.9544 0.3554 0.045 Uiso 1 1 calc R
C24 C 0.31916(8) 0.8572(5) 0.0246(3) 0.0271(7) Uani 1 1 d .
C7 C 0.55176(9) 0.3378(5) 0.4571(3) 0.0321(7) Uani 1 1 d .
H7A H 0.5467 0.1949 0.4503 0.048 Uiso 1 1 calc R
H7B H 0.5271 0.4092 0.4485 0.048 Uiso 1 1 calc R
H7C H 0.5689 0.3682 0.5493 0.048 Uiso 1 1 calc R
C15 C 0.67749(9) 0.6291(5) 0.6062(3) 0.0337(8) Uani 1 1 d .
H15 H 0.6770 0.7513 0.6549 0.040 Uiso 1 1 calc R
N4 N 0.54261(7) 0.3668(4) 0.2012(3) 0.0206(6) Uani 1 1 d .
H4A H 0.5339 0.2381 0.2000 0.025 Uiso 1 1 calc R
H4B H 0.5554 0.3801 0.1280 0.025 Uiso 1 1 calc R
C26 C 0.29587(9) 0.5927(6) -0.1419(3) 0.0421(10) Uani 1 1 d .
H26 H 0.2760 0.5372 -0.2143 0.050 Uiso 1 1 calc R
C25 C 0.28992(9) 0.7686(6) -0.0829(3) 0.0384(8) Uani 1 1 d .
H25 H 0.2657 0.8344 -0.1138 0.046 Uiso 1 1 calc R
C27 C 0.33094(9) 0.4925(5) -0.0973(3) 0.0364(8) Uani 1 1 d .
H27 H 0.3348 0.3689 -0.1395 0.044 Uiso 1 1 calc R
Cl2 Cl 0.53455(2) 0.82773(11) 0.19529(9) 0.02774(19) Uani 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'
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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 9 0 0.0452 -0.9019 9.0032 -0.0502 -0.2033 -0.8755 -0.2981
-8 8 -7 0.0906 -7.8758 7.9866 -7.0366 -0.1515 -0.6031 -0.8151
-13 0 -12 0.1135 -12.9353 -0.0276 -11.9867 0.0649 0.2991 -0.9506
0 -9 -1 0.0489 -0.0929 -9.0055 -0.9486 0.2072 0.9006 0.2197
-32 7 0 0.0379 -31.8741 7.0137 -0.0548 0.4128 -0.7289 -0.5241
-48 1 0 0.0393 -47.9131 1.0176 -0.0298 0.8532 -0.1708 -0.4813
-47 0 7 0.0780 -46.9512 0.0357 6.9646 0.9603 -0.2583 0.0437
-11 -3 13 0.1090 -11.0625 -2.9620 12.9895 0.4623 -0.0712 0.8913
48 -1 0 0.0357 47.9131 -1.0176 0.0298 -0.8532 0.1708 0.4813
49 0 -5 0.0604 48.9406 -0.0311 -4.9669 -0.9681 0.2082 0.1132
9 3 -13 0.1155 9.0657 2.9628 -12.9905 -0.4257 0.0681 -0.9100
-45 -3 -1 0.0401 -44.9571 -2.9874 -1.0045 0.8824 0.2488 -0.3940
45 4 0 0.0359 44.9715 3.9850 0.0007 -0.9214 -0.3193 0.2928
12 4 11 0.1105 11.9834 4.0265 10.9657 -0.1595 -0.6625 0.7438
19 -4 -12 0.1128 18.9711 -4.0403 -11.9484 -0.4218 0.7366 -0.5228
-28 2 12 0.1033 -27.9782 2.0429 11.9549 0.6357 -0.5562 0.5027
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_3
Cl3 Pd1 Pd1 94.74(2) 2_655
N5 Pd1 Pd1 94.63(7) 2_655
N5 Pd1 Cl3 91.03(8) .
N5 Pd1 N4 179.47(12) .
N5 Pd1 Cl2 88.18(8) .
N4 Pd1 Pd1 85.32(7) 2_655
N4 Pd1 Cl3 89.50(7) .
N4 Pd1 Cl2 91.29(8) .
Cl2 Pd1 Pd1 86.65(2) 2_655
Cl2 Pd1 Cl3 178.45(3) .
C19 N5 Pd1 115.45(18) .
C15 C16 C17 121.7(3) .
C22 C23 C24 120.8(3) .
C27 C28 C29 121.1(3) .
C20 C21 C22 121.9(3) .
C16 C17 C8 123.9(2) .
C16 C17 C12 117.4(2) .
C8 C17 C12 118.7(3) .
C10 C11 C12 120.8(3) .
C21 C20 C29 118.7(3) .
C21 C20 C19 121.3(3) .
C29 C20 C19 119.9(3) .
C28 C29 C20 123.2(3) .
C28 C29 C24 117.8(3) .
C24 C29 C20 119.0(3) .
N5 C19 C20 111.0(2) .
N5 C19 C18 106.8(2) .
C20 C19 C18 115.3(2) .
C23 C22 C21 120.2(3) .
C17 C8 C6 119.1(3) .
C9 C8 C17 119.4(3) .
C9 C8 C6 121.3(2) .
C7 C6 C8 111.6(2) .
N4 C6 C8 114.2(2) .
N4 C6 C7 107.3(2) .
C13 C14 C15 120.1(3) .
C11 C12 C17 119.4(3) .
C11 C12 C13 122.0(3) .
C13 C12 C17 118.7(3) .
C8 C9 C10 121.8(3) .
C14 C13 C12 121.8(3) .
C11 C10 C9 119.9(3) .
C23 C24 C29 119.5(3) .
C23 C24 C25 121.8(3) .
C25 C24 C29 118.8(3) .
C16 C15 C14 120.2(3) .
C6 N4 Pd1 115.19(18) .
C25 C26 C27 120.4(3) .
C26 C25 C24 121.3(3) .
C28 C27 C26 120.5(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 Pd1 3.2252(4) 2_655
Pd1 Cl3 2.3072(8) .
Pd1 N5 2.061(3) .
Pd1 N4 2.064(2) .
Pd1 Cl2 2.2946(8) .
N5 C19 1.504(4) .
C16 C17 1.427(5) .
C16 C15 1.367(4) .
C23 C22 1.357(5) .
C23 C24 1.417(5) .
C28 C29 1.418(5) .
C28 C27 1.373(4) .
C21 C20 1.377(4) .
C21 C22 1.413(4) .
C17 C8 1.428(4) .
C17 C12 1.434(4) .
C11 C12 1.412(4) .
C11 C10 1.364(4) .
C20 C29 1.440(4) .
C20 C19 1.518(4) .
C29 C24 1.427(4) .
C19 C18 1.522(4) .
C8 C6 1.524(4) .
C8 C9 1.367(4) .
C6 C7 1.512(4) .
C6 N4 1.494(3) .
C14 C13 1.356(5) .
C14 C15 1.404(4) .
C12 C13 1.420(4) .
C9 C10 1.411(4) .
C24 C25 1.423(4) .
C26 C25 1.351(5) .
C26 C27 1.392(5) .
