#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:35:21 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178572 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/82/4068293.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_4068293
loop_
_publ_author_name
'Lipke, Mark C.'
'Woloszynek, Robert A.'
'Ma, Liqing'
'Protasiewicz, John D.'
_publ_section_title
;
 m-Terphenyl Anchored Palladium Diphosphinite PCP-Pincer Complexes That
 Promote the Suzuki−Miyaura Reaction Under Mild Conditions
;
_journal_issue                   1
_journal_name_full               Organometallics
_journal_page_first              188
_journal_paper_doi               10.1021/om800626b
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C42 H31 I O2 P2 Pd'
_chemical_formula_weight         862.91
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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            4
_cell_length_a                   15.1802(5)
_cell_length_b                   11.6483(3)
_cell_length_c                   19.6981(6)
_cell_measurement_reflns_used    9095
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.17
_cell_measurement_theta_min      2.71
_cell_volume                     3483.09(18)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEX II 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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            78927
_diffrn_reflns_theta_full        33.18
_diffrn_reflns_theta_max         33.18
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    1.548
_exptl_absorpt_correction_T_max  0.8606
_exptl_absorpt_correction_T_min  0.4687
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.575
_refine_diff_density_min         -2.186
_refine_diff_density_rms         0.115
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         6639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0288
_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)+(0.0122P)²+9.4129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0594
_refine_ls_wR_factor_ref         0.0720
_reflns_number_gt                5186
_reflns_number_total             6639
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om800626b_si_001.cif
_cod_data_source_block           case01
_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 

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      Pbcn
_cod_database_code               4068293
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, 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 0.0000 0.404520(16) 0.2500 0.00986(4) Uani 1 2 d S
I1 I 0.0000 0.177818(16) 0.2500 0.02267(5) Uani 1 2 d S
C1 C 0.0000 0.5805(2) 0.2500 0.0117(4) Uani 1 2 d S
C2 C -0.06937(15) 0.64329(18) 0.22057(10) 0.0176(4) Uani 1 1 d .
C3 C -0.07036(19) 0.7634(2) 0.22251(12) 0.0245(5) Uani 1 1 d .
H21 H -0.1194 0.8044 0.2049 0.029(8) Uiso 1 1 calc R
C4 C 0.0000 0.8224(3) 0.2500 0.0298(8) Uani 1 2 d S
H22 H 0.0000 0.9040 0.2500 0.064(19) Uiso 1 2 calc SR
C5 C -0.14109(14) 0.58472(19) 0.18303(10) 0.0175(4) Uani 1 1 d .
C6 C -0.22987(16) 0.5921(2) 0.20083(13) 0.0254(5) Uani 1 1 d .
H17 H -0.2463 0.6339 0.2403 0.028(8) Uiso 1 1 calc R
C7 C -0.29433(16) 0.5397(2) 0.16226(16) 0.0324(6) Uani 1 1 d .
H16 H -0.3544 0.5446 0.1756 0.041(10) Uiso 1 1 calc R
C8 C -0.27130(17) 0.4801(2) 0.10402(15) 0.0306(5) Uani 1 1 d .
H15 H -0.3157 0.4446 0.0774 0.040(10) Uiso 1 1 calc R
C9 C -0.18394(16) 0.4721(2) 0.08446(12) 0.0223(4) Uani 1 1 d .
H14 H -0.1680 0.4316 0.0445 0.022(7) Uiso 1 1 calc R
C10 C -0.12059(14) 0.52395(18) 0.12408(10) 0.0162(4) Uani 1 1 d .
O1 O -0.03287(10) 0.52145(13) 0.10215(7) 0.0149(3) Uani 1 1 d .
P1 P 0.03063(3) 0.42585(4) 0.13735(2) 0.01246(9) Uani 1 1 d .
C11 C 0.02501(14) 0.31280(17) 0.07423(10) 0.0149(3) Uani 1 1 d .
C12 C -0.04642(15) 0.23663(19) 0.07442(11) 0.0181(4) Uani 1 1 d .
H12 H -0.0870 0.2373 0.1111 0.024(8) Uiso 1 1 calc R
C13 C -0.05798(17) 0.1601(2) 0.02102(12) 0.0230(4) Uani 1 1 d .
H11 H -0.1067 0.1089 0.0212 0.039(9) Uiso 1 1 calc R
C14 C 0.00139(17) 0.15846(19) -0.03249(11) 0.0225(4) Uani 1 1 d .
H10 H -0.0063 0.1055 -0.0687 0.031(9) Uiso 1 1 calc R
C15 C 0.07172(17) 0.2337(2) -0.03335(11) 0.0219(4) Uani 1 1 d .
H9 H 0.1119 0.2329 -0.0703 0.027(8) Uiso 1 1 calc R
C16 C 0.08379(15) 0.31054(18) 0.01985(10) 0.0177(4) Uani 1 1 d .
H8 H 0.1324 0.3619 0.0191 0.023(7) Uiso 1 1 calc R
C17 C 0.13814(14) 0.48752(18) 0.12564(10) 0.0156(4) Uani 1 1 d .
C18 C 0.21074(15) 0.4247(2) 0.14840(12) 0.0212(4) Uani 1 1 d .
H2 H 0.2021 0.3524 0.1697 0.031(8) Uiso 1 1 calc R
C19 C 0.29557(15) 0.4674(2) 0.14009(13) 0.0263(5) Uani 1 1 d .
H3 H 0.3448 0.4240 0.1552 0.037(9) Uiso 1 1 calc R
C20 C 0.30809(16) 0.5737(2) 0.10955(12) 0.0269(5) Uani 1 1 d .
H4 H 0.3660 0.6028 0.1032 0.029(8) Uiso 1 1 calc R
C21 C 0.23577(17) 0.6370(2) 0.08838(13) 0.0258(5) Uani 1 1 d .
H5 H 0.2445 0.7102 0.0682 0.036(9) Uiso 1 1 calc R
C22 C 0.15068(16) 0.5948(2) 0.09636(12) 0.0214(4) Uani 1 1 d .
H6 H 0.1015 0.6390 0.0819 0.021(7) 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'
O O 0.0106 0.0060 '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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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 P1 83.748(14) . 3
C1 Pd1 P1 83.747(14) . .
P1 Pd1 P1 167.49(3) 3 .
C1 Pd1 I1 180.0 . .
P1 Pd1 I1 96.252(14) 3 .
P1 Pd1 I1 96.253(14) . .
C2 C1 C2 117.4(3) 3 .
C2 C1 Pd1 121.32(13) 3 .
C2 C1 Pd1 121.32(13) . .
C3 C2 C1 121.1(2) . .
C3 C2 C5 117.8(2) . .
C1 C2 C5 121.06(19) . .
C4 C3 C2 120.0(2) . .
C3 C4 C3 120.3(3) . 3
C10 C5 C6 117.1(2) . .
C10 C5 C2 119.00(19) . .
C6 C5 C2 123.8(2) . .
C7 C6 C5 121.3(2) . .
C6 C7 C8 119.9(2) . .
C9 C8 C7 120.4(2) . .
C10 C9 C8 118.8(2) . .
C9 C10 C5 122.5(2) . .
C9 C10 O1 118.68(19) . .
C5 C10 O1 118.65(19) . .
C10 O1 P1 116.48(13) . .
O1 P1 C17 102.09(9) . .
O1 P1 C11 100.19(9) . .
C17 P1 C11 104.18(10) . .
O1 P1 Pd1 111.61(6) . .
C17 P1 Pd1 110.70(7) . .
C11 P1 Pd1 125.34(7) . .
C16 C11 C12 119.03(19) . .
C16 C11 P1 120.69(16) . .
C12 C11 P1 119.64(16) . .
C13 C12 C11 120.1(2) . .
C14 C13 C12 120.1(2) . .
C15 C14 C13 120.2(2) . .
C14 C15 C16 120.1(2) . .
C15 C16 C11 120.5(2) . .
C22 C17 C18 119.8(2) . .
C22 C17 P1 122.48(17) . .
C18 C17 P1 117.75(16) . .
C19 C18 C17 120.4(2) . .
C20 C19 C18 119.8(2) . .
C21 C20 C19 119.7(2) . .
C20 C21 C22 120.9(2) . .
C17 C22 C21 119.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 2.050(3) .
Pd1 P1 2.2807(5) 3
Pd1 P1 2.2807(5) .
Pd1 I1 2.6407(3) .
C1 C2 1.407(3) 3
C1 C2 1.407(3) .
C2 C3 1.400(3) .
C2 C5 1.482(3) .
C3 C4 1.380(3) .
C4 C3 1.380(3) 3
C5 C10 1.395(3) .
C5 C6 1.395(3) .
C6 C7 1.381(4) .
C7 C8 1.386(4) .
C8 C9 1.384(4) .
C9 C10 1.378(3) .
C10 O1 1.400(3) .
O1 P1 1.6279(15) .
P1 C17 1.798(2) .
P1 C11 1.813(2) .
C11 C16 1.394(3) .
C11 C12 1.401(3) .
C12 C13 1.390(3) .
C13 C14 1.387(3) .
C14 C15 1.381(4) .
C15 C16 1.391(3) .
C17 C22 1.389(3) .
C17 C18 1.397(3) .
C18 C19 1.390(3) .
C19 C20 1.389(4) .
C20 C21 1.387(4) .
C21 C22 1.391(3) .
