#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:37:51 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178574 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/84/4068439.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_4068439
loop_
_publ_author_name
'Kantchev, Eric Assen B.'
'Ying, Jackie Y.'
_publ_section_title
;
 Practical One-Pot, Three-Component Synthesis of N-Heterocyclic Carbene
 (NHC) Ligated Palladacycles Derived fromN,N-Dimethylbenzylamine
;
_journal_issue                   1
_journal_name_full               Organometallics
_journal_page_first              289
_journal_paper_doi               10.1021/om8008475
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C36 H48 Cl N3 Pd'
_chemical_formula_weight         664.62
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.5682(5)
_cell_length_b                   18.4516(7)
_cell_length_c                   26.1633(10)
_cell_measurement_reflns_used    3756
_cell_measurement_temperature    243(2)
_cell_measurement_theta_max      20.02
_cell_measurement_theta_min      2.34
_cell_volume                     7032.9(4)
_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      243(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0713
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            39455
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.9059
_exptl_absorpt_correction_T_min  0.8049
_exptl_absorpt_correction_type   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             2784
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.864
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         6181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0671
_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)+(0.0615P)²+3.8664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1495
_reflns_number_gt                4536
_reflns_number_total             6181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om8008475_si_002.cif
_cod_data_source_block           6420
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4068439
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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 0.47252(3) 0.05286(2) 0.637465(15) 0.05537(17) Uani 1 1 d .
Cl1 Cl 0.55566(10) 0.12323(10) 0.69898(6) 0.0843(5) Uani 1 1 d .
N1 N 0.3128(3) 0.0923(2) 0.70494(13) 0.0482(9) Uani 1 1 d .
N2 N 0.2962(3) 0.1400(2) 0.63029(13) 0.0520(10) Uani 1 1 d .
N3 N 0.5952(3) 0.0001(3) 0.6131(2) 0.0906(17) Uani 1 1 d .
C1 C 0.3538(3) 0.0980(3) 0.65842(18) 0.0455(11) Uani 1 1 d .
C2 C 0.2303(3) 0.1300(3) 0.70538(19) 0.0573(13) Uani 1 1 d .
H2 H 0.1892 0.1335 0.7329 0.069 Uiso 1 1 calc R
C3 C 0.2203(3) 0.1602(3) 0.65954(19) 0.0613(14) Uani 1 1 d .
H3 H 0.1713 0.1897 0.6489 0.074 Uiso 1 1 calc R
C4 C 0.3513(3) 0.0606(3) 0.75078(19) 0.0566(13) Uani 1 1 d .
C5 C 0.3811(4) 0.1079(3) 0.7896(2) 0.0663(15) Uani 1 1 d .
C6 C 0.4160(5) 0.0760(5) 0.8331(3) 0.102(2) Uani 1 1 d .
H6 H 0.4369 0.1059 0.8598 0.123 Uiso 1 1 calc R
C7 C 0.4211(6) 0.0038(6) 0.8388(3) 0.127(3) Uani 1 1 d .
H7 H 0.4459 -0.0155 0.8690 0.152 Uiso 1 1 calc R
C8 C 0.3907(6) -0.0423(4) 0.8010(3) 0.117(3) Uani 1 1 d .
H8 H 0.3951 -0.0928 0.8055 0.140 Uiso 1 1 calc R
C9 C 0.3532(4) -0.0140(3) 0.7559(2) 0.0780(17) Uani 1 1 d .
C10 C 0.3753(4) 0.1888(3) 0.7862(2) 0.0768(17) Uani 1 1 d .
H10 H 0.3622 0.2017 0.7502 0.092 Uiso 1 1 calc R
C11 C 0.2964(5) 0.2177(3) 0.8192(3) 0.096(2) Uani 1 1 d .
H11A H 0.2389 0.1970 0.8076 0.144 Uiso 1 1 calc R
H11B H 0.2938 0.2701 0.8164 0.144 Uiso 1 1 calc R
H11C H 0.3068 0.2043 0.8546 0.144 Uiso 1 1 calc R
C12 C 0.4645(5) 0.2266(4) 0.8017(3) 0.121(3) Uani 1 1 d .
H12A H 0.4733 0.2219 0.8383 0.181 Uiso 1 1 calc R
H12B H 0.4610 0.2776 0.7927 0.181 Uiso 1 1 calc R
H12C H 0.5158 0.2044 0.7839 0.181 Uiso 1 1 calc R
C13 C 0.3113(7) -0.0633(3) 0.7157(3) 0.110(3) Uani 1 1 d .
H13 H 0.3189 -0.0381 0.6825 0.132 Uiso 1 1 calc R
C14 C 0.2068(8) -0.0716(6) 0.7241(4) 0.202(6) Uani 1 1 d .
H14A H 0.1781 -0.0873 0.6925 0.302 Uiso 1 1 calc R
H14B H 0.1810 -0.0254 0.7344 0.302 Uiso 1 1 calc R
H14C H 0.1957 -0.1074 0.7506 0.302 Uiso 1 1 calc R
C15 C 0.3576(9) -0.1352(4) 0.7102(4) 0.191(6) Uani 1 1 d .
H15A H 0.4233 -0.1280 0.7066 0.286 Uiso 1 1 calc R
H15B H 0.3341 -0.1598 0.6802 0.286 Uiso 1 1 calc R
H15C H 0.3456 -0.1644 0.7403 0.286 Uiso 1 1 calc R
C16 C 0.3102(3) 0.1684(3) 0.57925(18) 0.0558(13) Uani 1 1 d .
C17 C 0.2470(4) 0.1490(3) 0.54117(19) 0.0643(15) Uani 1 1 d .
C18 C 0.2580(5) 0.1805(4) 0.4931(2) 0.0830(19) Uani 1 1 d .
H18 H 0.2180 0.1678 0.4664 0.100 Uiso 1 1 calc R
C19 C 0.3257(6) 0.2291(4) 0.4845(3) 0.096(2) Uani 1 1 d .
H19 H 0.3319 0.2498 0.4518 0.116 Uiso 1 1 calc R
C20 C 0.3850(5) 0.2488(4) 0.5221(3) 0.0837(18) Uani 1 1 d .
H20 H 0.4306 0.2835 0.5153 0.100 Uiso 1 1 calc R
C21 C 0.3793(4) 0.2183(3) 0.5709(2) 0.0647(14) Uani 1 1 d .
C22 C 0.1664(4) 0.0989(4) 0.5490(2) 0.0857(19) Uani 1 1 d .
H22 H 0.1745 0.0745 0.5825 0.103 Uiso 1 1 calc R
C23 C 0.0757(4) 0.1422(5) 0.5511(3) 0.120(3) Uani 1 1 d .
H23A H 0.0777 0.1759 0.5795 0.179 Uiso 1 1 calc R
H23B H 0.0247 0.1091 0.5556 0.179 Uiso 1 1 calc R
H23C H 0.0679 0.1689 0.5194 0.179 Uiso 1 1 calc R
C24 C 0.1594(6) 0.0396(4) 0.5076(3) 0.120(3) Uani 1 1 d .
H24A H 0.1445 0.0618 0.4750 0.180 Uiso 1 1 calc R
H24B H 0.1116 0.0054 0.5168 0.180 Uiso 1 1 calc R
H24C H 0.2176 0.0144 0.5048 0.180 Uiso 1 1 calc R
C25 C 0.4439(4) 0.2438(3) 0.6126(2) 0.0769(17) Uani 1 1 d .
H25 H 0.4448 0.2055 0.6391 0.092 Uiso 1 1 calc R
C26 C 0.4079(7) 0.3121(6) 0.6379(4) 0.171(5) Uani 1 1 d .
H26A H 0.4005 0.3498 0.6123 0.257 Uiso 1 1 calc R
H26B H 0.4512 0.3282 0.6637 0.257 Uiso 1 1 calc R
H26C H 0.3491 0.3021 0.6538 0.257 Uiso 1 1 calc R
C27 C 0.5423(4) 0.2551(5) 0.5958(3) 0.127(3) Uani 1 1 d .
H27A H 0.5649 0.2113 0.5796 0.191 Uiso 1 1 calc R
H27B H 0.5799 0.2664 0.6253 0.191 Uiso 1 1 calc R
H27C H 0.5450 0.2949 0.5716 0.191 Uiso 1 1 calc R
C28 C 0.4145(4) -0.0185(3) 0.5896(2) 0.0601(13) Uani 1 1 d .
C29 C 0.3252(4) -0.0401(3) 0.5863(2) 0.0727(16) Uani 1 1 d .
H29 H 0.2798 -0.0142 0.6041 0.087 Uiso 1 1 calc R
C30 C 0.2997(5) -0.1003(4) 0.5568(3) 0.092(2) Uani 1 1 d .
H30 H 0.2380 -0.1151 0.5559 0.110 Uiso 1 1 calc R
C31 C 0.3632(7) -0.1373(4) 0.5296(4) 0.121(3) Uani 1 1 d .
H31 H 0.3460 -0.1776 0.5099 0.145 Uiso 1 1 calc R
C32 C 0.4527(6) -0.1154(5) 0.5312(4) 0.138(3) Uani 1 1 d .
H32 H 0.4972 -0.1406 0.5122 0.165 Uiso 1 1 calc R
C33 C 0.4781(5) -0.0565(4) 0.5605(3) 0.093(2) Uani 1 1 d .
C34 C 0.5758(4) -0.0297(4) 0.5616(3) 0.113(3) Uani 1 1 d .
H34A H 0.6181 -0.0697 0.5541 0.136 Uiso 1 1 calc R
H34B H 0.5845 0.0080 0.5357 0.136 Uiso 1 1 calc R
C35 C 0.6773(4) 0.0460(5) 0.6094(3) 0.137(4) Uani 1 1 d .
H35A H 0.7291 0.0169 0.5985 0.206 Uiso 1 1 calc R
H35B H 0.6904 0.0671 0.6426 0.206 Uiso 1 1 calc R
H35C H 0.6666 0.0844 0.5849 0.206 Uiso 1 1 calc R
C36 C 0.6103(7) -0.0599(5) 0.6502(4) 0.174(5) Uani 1 1 d .
H36A H 0.6659 -0.0859 0.6412 0.261 Uiso 1 1 calc R
H36B H 0.5584 -0.0928 0.6492 0.261 Uiso 1 1 calc R
H36C H 0.6164 -0.0400 0.6844 0.261 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'
Pd Pd -0.9988 1.0072 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 Pd1 C28 94.61(19)
C1 Pd1 N3 176.9(2)
C28 Pd1 N3 82.4(2)
C1 Pd1 Cl1 91.56(13)
C28 Pd1 Cl1 171.41(16)
N3 Pd1 Cl1 91.40(15)
C1 N1 C2 110.4(4)
C1 N1 C4 127.1(4)
C2 N1 C4 122.0(4)
C1 N2 C3 110.2(4)
C1 N2 C16 128.2(4)
C3 N2 C16 121.3(4)
C35 N3 C34 108.1(6)
C35 N3 C36 110.5(6)
C34 N3 C36 110.2(7)
C35 N3 Pd1 116.0(4)
C34 N3 Pd1 106.4(4)
C36 N3 Pd1 105.5(5)
N2 C1 N1 104.9(4)
N2 C1 Pd1 128.6(3)
N1 C1 Pd1 126.4(3)
C3 C2 N1 107.3(4)
C2 C3 N2 107.2(4)
C9 C4 C5 122.7(5)
C9 C4 N1 119.4(5)
C5 C4 N1 117.9(5)
C6 C5 C4 116.5(6)
C6 C5 C10 119.6(6)
C4 C5 C10 123.9(5)
C7 C6 C5 122.3(7)
C6 C7 C8 121.1(7)
C7 C8 C9 119.9(7)
C4 C9 C8 117.5(7)
C4 C9 C13 121.3(6)
C8 C9 C13 121.1(7)
C5 C10 C12 113.1(6)
C5 C10 C11 110.8(5)
C12 C10 C11 109.1(5)
C15 C13 C9 114.5(8)
C15 C13 C14 111.7(8)
C9 C13 C14 111.0(6)
C21 C16 C17 122.3(5)
C21 C16 N2 119.3(5)
C17 C16 N2 118.1(5)
C18 C17 C16 117.3(6)
C18 C17 C22 117.9(5)
C16 C17 C22 124.7(5)
C19 C18 C17 120.7(6)
C18 C19 C20 121.3(6)
C19 C20 C21 121.1(6)
C16 C21 C20 117.2(6)
C16 C21 C25 123.0(5)
C20 C21 C25 119.7(6)
C17 C22 C24 113.0(5)
C17 C22 C23 110.6(6)
C24 C22 C23 109.5(6)
C27 C25 C21 114.9(6)
C27 C25 C26 109.8(7)
C21 C25 C26 111.0(6)
C29 C28 C33 116.9(5)
C29 C28 Pd1 129.4(4)
C33 C28 Pd1 113.2(4)
C28 C29 C30 121.3(6)
C31 C30 C29 120.5(7)
C30 C31 C32 119.2(7)
C31 C32 C33 120.4(7)
C32 C33 C28 121.5(7)
C32 C33 C34 121.5(6)
C28 C33 C34 116.9(5)
N3 C34 C33 108.6(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C1 1.996(4)
Pd1 C28 2.003(5)
Pd1 N3 2.133(5)
Pd1 Cl1 2.3965(15)
N1 C1 1.360(6)
N1 C2 1.389(6)
N1 C4 1.447(6)
N2 C1 1.359(6)
N2 C3 1.396(6)
N2 C16 1.449(6)
N3 C35 1.469(9)
N3 C34 1.482(8)
N3 C36 1.489(10)
C2 C3 1.331(6)
C4 C9 1.384(7)
C4 C5 1.406(7)
C5 C6 1.379(8)
C5 C10 1.498(8)
C6 C7 1.342(11)
C7 C8 1.377(11)
C8 C9 1.402(10)
C9 C13 1.520(10)
C10 C12 1.530(8)
C10 C11 1.534(8)
C13 C15 1.496(10)
C13 C14 1.545(12)
C16 C21 1.382(7)
C16 C17 1.403(7)
C17 C18 1.395(7)
C17 C22 1.509(8)
C18 C19 1.351(9)
C19 C20 1.360(9)
C20 C21 1.396(8)
C21 C25 1.516(8)
C22 C24 1.544(9)
C22 C23 1.545(9)
C25 C27 1.513(8)
C25 C26 1.518(10)
C28 C29 1.364(7)
C28 C33 1.390(8)
C29 C30 1.403(8)
C30 C31 1.351(10)
C31 C32 1.365(11)
C32 C33 1.380(10)
C33 C34 1.508(9)
