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#$Date: 2016-03-21 02:25:28 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178388 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/10/4021086.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_4021086
loop_
_publ_author_name
'Gary A. Molander'
'Jason P. Burke'
'Patrick J. Carroll'
_publ_section_title
;
 Synthesis and Application of Chiral Cyclopropane-Based Ligands
 in Palladium-Catalyzed Allylic Alkylation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8062
_journal_page_last               8069
_journal_paper_doi               10.1021/jo048782s
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C25 H27 Cl2 P Pd S'
_chemical_formula_weight         567.80
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 101.117(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5511(7)
_cell_length_b                   17.748(1)
_cell_length_c                   14.4104(10)
_cell_measurement_temperature    143(1)
_cell_volume                     2396.9(3)
_diffrn_ambient_temperature      143(1)
_exptl_crystal_density_diffrn    1.573
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4021086
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.270258(18) 0.060614(9) 0.747071(11) 0.01427(6) Uani 1 1 d . . .
Cl1 Cl 0.32964(7) -0.02832(3) 0.64451(4) 0.02461(13) Uani 1 1 d . . .
Cl2 Cl 0.16534(6) -0.03361(3) 0.82744(4) 0.02250(13) Uani 1 1 d . . .
S1 S 0.20875(6) 0.14472(3) 0.85227(4) 0.01536(12) Uani 1 1 d . . .
P1 P 0.35080(6) 0.14575(3) 0.65563(4) 0.01485(12) Uani 1 1 d . . .
C1 C 0.3142(2) 0.24299(12) 0.67684(16) 0.0188(5) Uani 1 1 d . . .
H1 H 0.3579 0.2787 0.6391 0.025 Uiso 1 1 calc R . .
C2 C 0.1623(3) 0.26265(14) 0.68491(17) 0.0246(5) Uani 1 1 d . . .
H2A H 0.1188 0.3063 0.6504 0.033 Uiso 1 1 calc R . .
H2B H 0.0972 0.2214 0.6893 0.033 Uiso 1 1 calc R . .
C3 C 0.2810(3) 0.27595(13) 0.76728(17) 0.0216(5) Uani 1 1 d . . .
H3 H 0.3068 0.3294 0.7743 0.029 Uiso 1 1 calc R . .
C4 C 0.2967(3) 0.23698(12) 0.86123(16) 0.0192(5) Uani 1 1 d . . .
H4 H 0.3984 0.2303 0.8877 0.026 Uiso 1 1 calc R . .
C5 C 0.2290(3) 0.28390(14) 0.92970(19) 0.0345(7) Uani 1 1 d . . .
H5A H 0.2777 0.3313 0.9407 0.052 Uiso 1 1 calc R . .
H5B H 0.2366 0.2573 0.9885 0.052 Uiso 1 1 calc R . .
H5C H 0.1303 0.2925 0.9030 0.052 Uiso 1 1 calc R . .
C6 C 0.2691(2) 0.10940(12) 0.97021(15) 0.0169(5) Uani 1 1 d . . .
C7 C 0.1598(3) 0.09418(13) 1.02045(17) 0.0217(5) Uani 1 1 d . . .
C8 C 0.1994(3) 0.06686(13) 1.11252(17) 0.0267(6) Uani 1 1 d . . .
H8 H 0.1292 0.0556 1.1470 0.035 Uiso 1 1 calc R . .
C9 C 0.3406(3) 0.05632(14) 1.15326(17) 0.0286(6) Uani 1 1 d . . .
H9 H 0.3651 0.0387 1.2151 0.038 Uiso 1 1 calc R . .
C10 C 0.4458(3) 0.07180(13) 1.10262(17) 0.0250(5) Uani 1 1 d . . .
H10 H 0.5407 0.0647 1.1313 0.033 Uiso 1 1 calc R . .
C11 C 0.4140(3) 0.09787(12) 1.00946(16) 0.0196(5) Uani 1 1 d . . .
C12 C 0.0041(3) 0.10618(15) 0.97852(19) 0.0294(6) Uani 1 1 d . . .
H12A H -0.0530 0.0891 1.0224 0.044 Uiso 1 1 calc R . .
H12B H -0.0206 0.0782 0.9206 0.044 Uiso 1 1 calc R . .
H12C H -0.0132 0.1588 0.9659 0.044 Uiso 1 1 calc R . .
C13 C 0.5357(3) 0.11155(14) 0.95867(18) 0.0246(5) Uani 1 1 d . . .
H13A H 0.5673 0.1628 0.9683 0.037 Uiso 1 1 calc R . .
H13B H 0.5041 0.1024 0.8923 0.037 Uiso 1 1 calc R . .
H13C H 0.6130 0.0781 0.9831 0.037 Uiso 1 1 calc R . .
C14 C 0.5414(2) 0.13673(13) 0.66237(16) 0.0195(5) Uani 1 1 d . . .
C15 C 0.6351(3) 0.17761(15) 0.73001(19) 0.0273(6) Uani 1 1 d . . .
H15 H 0.6000 0.2142 0.7657 0.036 Uiso 1 1 calc R . .
C16 C 0.7802(3) 0.16386(18) 0.7442(2) 0.0367(7) Uani 1 1 d . . .
H16 H 0.8423 0.1908 0.7899 0.049 Uiso 1 1 calc R . .
C17 C 0.8330(3) 0.11038(16) 0.6908(2) 0.0353(7) Uani 1 1 d . . .
H17 H 0.9305 0.1008 0.7014 0.047 Uiso 1 1 calc R . .
C18 C 0.7417(3) 0.07096(14) 0.6216(2) 0.0293(6) Uani 1 1 d . . .
H18 H 0.7779 0.0359 0.5844 0.039 Uiso 1 1 calc R . .
C19 C 0.5968(3) 0.08383(14) 0.60771(18) 0.0234(5) Uani 1 1 d . . .
H19 H 0.5354 0.0570 0.5615 0.031 Uiso 1 1 calc R . .
C20 C 0.2654(2) 0.13542(13) 0.53250(16) 0.0196(5) Uani 1 1 d . . .
C21 C 0.3320(3) 0.15980(14) 0.46048(17) 0.0261(5) Uani 1 1 d . . .
H21 H 0.4234 0.1801 0.4748 0.035 Uiso 1 1 calc R . .
C22 C 0.2620(3) 0.15391(15) 0.36680(18) 0.0330(6) Uani 1 1 d . . .
H22 H 0.3076 0.1693 0.3185 0.044 Uiso 1 1 calc R . .
C23 C 0.1256(3) 0.12548(15) 0.34530(18) 0.0312(6) Uani 1 1 d . . .
H23 H 0.0792 0.1220 0.2825 0.042 Uiso 1 1 calc R . .
C24 C 0.0574(3) 0.10218(15) 0.41581(19) 0.0298(6) Uani 1 1 d . . .
H24 H -0.0351 0.0834 0.4009 0.040 Uiso 1 1 calc R . .
C25 C 0.1273(3) 0.10674(14) 0.50987(18) 0.0239(5) Uani 1 1 d . . .
H25 H 0.0816 0.0906 0.5577 0.032 Uiso 1 1 calc R . .
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 P1 2.2364(6) . ?
Pd1 S1 2.2836(6) . ?
Pd1 Cl1 2.3067(6) . ?
Pd1 Cl2 2.3643(6) . ?
S1 C6 1.799(2) . ?
S1 C4 1.833(2) . ?
P1 C1 1.799(2) . ?
P1 C14 1.811(2) . ?
P1 C20 1.814(2) . ?
C1 C3 1.517(3) . ?
C1 C2 1.518(3) . ?
C2 C3 1.494(3) . ?
C3 C4 1.502(3) . ?
C4 C5 1.527(3) . ?
C6 C11 1.405(3) . ?
C6 C7 1.407(3) . ?
C7 C8 1.395(3) . ?
C7 C12 1.509(4) . ?
C8 C9 1.375(4) . ?
C9 C10 1.379(4) . ?
C10 C11 1.397(3) . ?
C11 C13 1.507(3) . ?
C14 C15 1.393(3) . ?
C14 C19 1.394(3) . ?
C15 C16 1.383(4) . ?
C16 C17 1.378(4) . ?
C17 C18 1.382(4) . ?
C18 C19 1.379(3) . ?
C20 C21 1.387(3) . ?
C20 C25 1.393(3) . ?
C21 C22 1.390(3) . ?
C22 C23 1.376(4) . ?
C23 C24 1.372(4) . ?
C24 C25 1.393(3) . ?
