#------------------------------------------------------------------------------
#$Date: 2019-11-26 16:31:46 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243637 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/94/4089419.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_4089419
loop_
_publ_author_name
'Choi, Jun-Chul'
'Shiraishi, Kouichi'
'Takenaka, Yasumasa'
'Yasuda, Hiroyuki'
'Sakakura, Toshiyasu'
_publ_section_title
;
 Synthesis and Reactivity of Five-Membered Palladalactones from
 Arylallenes and Carbon Dioxide: Relevance to Catalytic Lactone Synthesis
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              3411
_journal_paper_doi               10.1021/om400089n
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C24 H34 P2 Pd'
_chemical_formula_sum            'C24 H34 P2 Pd'
_chemical_formula_weight         490.85
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_cell_setting           orthorhombic
_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                   11.5722(7)
_cell_length_b                   15.5202(9)
_cell_length_c                   13.4168(8)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.20
_cell_volume                     2409.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      123(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating unit'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25249
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.20
_diffrn_standards_number         0.0
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  0.8391
_exptl_absorpt_correction_T_min  0.7125
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadads
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.089
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0262
_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)+(0.0461P)²+1.6195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0779
_reflns_number_gt                2439
_reflns_number_total             2766
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400089n_si_002.cif
_cod_data_source_block           3a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               4089419
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'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 0.5000 0.447485(11) 0.2500 0.01926(9) Uani 1 2 d S
P1 P 0.61584(4) 0.54627(3) 0.16718(4) 0.02495(12) Uani 1 1 d .
C1 C 0.5552(2) 0.64280(14) 0.1115(2) 0.0460(6) Uani 1 1 d .
H1 H 0.5206 0.6787 0.1636 0.069 Uiso 1 1 calc R
H2 H 0.4958 0.6266 0.0629 0.069 Uiso 1 1 calc R
H3 H 0.6165 0.6752 0.0778 0.069 Uiso 1 1 calc R
C2 C 0.7261(2) 0.58948(17) 0.24975(16) 0.0412(6) Uani 1 1 d .
H4 H 0.7747 0.6303 0.2129 0.062 Uiso 1 1 calc R
H5 H 0.7741 0.5423 0.2751 0.062 Uiso 1 1 calc R
H6 H 0.6891 0.6192 0.3057 0.062 Uiso 1 1 calc R
C3 C 0.7040(2) 0.50626(15) 0.06440(19) 0.0481(6) Uani 1 1 d .
H7 H 0.6538 0.4896 0.0088 0.072 Uiso 1 1 calc R
H8 H 0.7484 0.4561 0.0867 0.072 Uiso 1 1 calc R
H9 H 0.7572 0.5516 0.0425 0.072 Uiso 1 1 calc R
C4 C 0.58483(15) 0.34585(10) 0.17749(13) 0.0217(3) Uani 1 1 d .
H10 H 0.5849 0.3562 0.1047 0.026 Uiso 1 1 calc R
H11 H 0.6661 0.3429 0.2003 0.026 Uiso 1 1 calc R
C5 C 0.52568(15) 0.26271(11) 0.19935(13) 0.0207(3) Uani 1 1 d .
C6 C 0.50792(14) 0.19463(12) 0.13804(14) 0.0215(4) Uani 1 1 d .
H12 H 0.4593 0.1507 0.1639 0.026 Uiso 1 1 calc R
C7 C 0.55308(15) 0.17897(11) 0.03728(13) 0.0216(3) Uani 1 1 d .
C8 C 0.49595(16) 0.11777(14) -0.02172(15) 0.0276(4) Uani 1 1 d .
H13 H 0.4292 0.0898 0.0038 0.033 Uiso 1 1 calc R
C9 C 0.5350(2) 0.09716(15) -0.11677(15) 0.0357(5) Uani 1 1 d .
H14 H 0.4945 0.0558 -0.1556 0.043 Uiso 1 1 calc R
C10 C 0.6327(2) 0.13669(14) -0.15500(15) 0.0369(5) Uani 1 1 d .
H15 H 0.6585 0.1235 -0.2205 0.044 Uiso 1 1 calc R
C11 C 0.69258(18) 0.19576(12) -0.09691(14) 0.0304(4) Uani 1 1 d .
H16 H 0.7607 0.2221 -0.1222 0.037 Uiso 1 1 calc R
C12 C 0.65345(16) 0.21656(11) -0.00206(14) 0.0244(4) Uani 1 1 d .
H17 H 0.6954 0.2570 0.0369 0.029 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'
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'
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
C4 Pd1 C4 82.45(9) 3_655 .
C4 Pd1 P1 90.25(5) 3_655 3_655
C4 Pd1 P1 171.77(5) . 3_655
C4 Pd1 P1 171.77(5) 3_655 .
C4 Pd1 P1 90.25(5) . .
P1 Pd1 P1 97.27(2) 3_655 .
C1 P1 C2 102.58(12) . .
C1 P1 C3 100.71(12) . .
C2 P1 C3 101.16(12) . .
C1 P1 Pd1 121.28(8) . .
C2 P1 Pd1 110.95(8) . .
C3 P1 Pd1 117.40(7) . .
P1 C1 H1 109.5 . .
P1 C1 H2 109.5 . .
H1 C1 H2 109.5 . .
P1 C1 H3 109.5 . .
H1 C1 H3 109.5 . .
H2 C1 H3 109.5 . .
P1 C2 H4 109.5 . .
P1 C2 H5 109.5 . .
H4 C2 H5 109.5 . .
P1 C2 H6 109.5 . .
H4 C2 H6 109.5 . .
H5 C2 H6 109.5 . .
P1 C3 H7 109.5 . .
P1 C3 H8 109.5 . .
H7 C3 H8 109.5 . .
P1 C3 H9 109.5 . .
H7 C3 H9 109.5 . .
H8 C3 H9 109.5 . .
C5 C4 Pd1 110.19(11) . .
C5 C4 H10 109.6 . .
Pd1 C4 H10 109.6 . .
C5 C4 H11 109.6 . .
Pd1 C4 H11 109.6 . .
H10 C4 H11 108.1 . .
C6 C5 C5 119.70(13) . 3_655
C6 C5 C4 128.73(16) . .
C5 C5 C4 111.37(11) 3_655 .
C5 C6 C7 129.31(17) . .
C5 C6 H12 115.3 . .
C7 C6 H12 115.3 . .
C8 C7 C12 117.37(16) . .
C8 C7 C6 117.62(16) . .
C12 C7 C6 124.87(16) . .
C9 C8 C7 121.36(18) . .
C9 C8 H13 119.3 . .
C7 C8 H13 119.3 . .
C10 C9 C8 120.2(2) . .
C10 C9 H14 119.9 . .
C8 C9 H14 119.9 . .
C9 C10 C11 119.48(19) . .
C9 C10 H15 120.3 . .
C11 C10 H15 120.3 . .
C12 C11 C10 120.33(18) . .
C12 C11 H16 119.8 . .
C10 C11 H16 119.8 . .
C11 C12 C7 121.20(17) . .
C11 C12 H17 119.4 . .
C7 C12 H17 119.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C4 2.0973(16) 3_655
Pd1 C4 2.0973(16) .
Pd1 P1 2.3200(5) 3_655
Pd1 P1 2.3200(5) .
P1 C1 1.815(2) .
P1 C2 1.818(2) .
P1 C3 1.824(2) .
C1 H1 0.9800 .
C1 H2 0.9800 .
C1 H3 0.9800 .
C2 H4 0.9800 .
C2 H5 0.9800 .
C2 H6 0.9800 .
C3 H7 0.9800 .
C3 H8 0.9800 .
C3 H9 0.9800 .
C4 C5 1.490(2) .
C4 H10 0.9900 .
C4 H11 0.9900 .
C5 C6 1.355(3) .
C5 C5 1.484(3) 3_655
C6 C7 1.470(2) .
C6 H12 0.9500 .
C7 C8 1.402(3) .
C7 C12 1.403(2) .
C8 C9 1.390(3) .
C8 H13 0.9500 .
C9 C10 1.384(3) .
C9 H14 0.9500 .
C10 C11 1.389(3) .
C10 H15 0.9500 .
C11 C12 1.389(3) .
C11 H16 0.9500 .
C12 H17 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C4 Pd1 P1 C1 162.8(4) 3_655 .
C4 Pd1 P1 C1 135.39(12) . .
P1 Pd1 P1 C1 -41.26(11) 3_655 .
C4 Pd1 P1 C2 -76.8(4) 3_655 .
C4 Pd1 P1 C2 -104.25(11) . .
P1 Pd1 P1 C2 79.10(10) 3_655 .
C4 Pd1 P1 C3 38.8(4) 3_655 .
C4 Pd1 P1 C3 11.33(12) . .
P1 Pd1 P1 C3 -165.32(11) 3_655 .
C4 Pd1 C4 C5 11.28(8) 3_655 .
P1 Pd1 C4 C5 -16.4(4) 3_655 .
P1 Pd1 C4 C5 -172.53(12) . .
Pd1 C4 C5 C6 142.56(16) . .
Pd1 C4 C5 C5 -32.4(2) . 3_655
C5 C5 C6 C7 -177.45(18) 3_655 .
C4 C5 C6 C7 8.0(3) . .
C5 C6 C7 C8 -161.20(19) . .
C5 C6 C7 C12 23.1(3) . .
C12 C7 C8 C9 -2.0(3) . .
C6 C7 C8 C9 -178.05(19) . .
C7 C8 C9 C10 0.5(3) . .
C8 C9 C10 C11 1.3(3) . .
C9 C10 C11 C12 -1.5(3) . .
C10 C11 C12 C7 -0.1(3) . .
C8 C7 C12 C11 1.9(3) . .
C6 C7 C12 C11 177.55(17) . .
