#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/33/4063325.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_4063325
loop_
_publ_author_name
'Seiji Ogo'
'Yoshitaka Takebe'
'Keiji Uehara'
'Takayuki Yamazaki'
'Hidetaka Nakai'
'Yoshihito Watanabe'
'Shunichi Fukuzumi'
_publ_section_title
;
 pH-Dependent C-C Coupling Reactions Catalyzed by Water-Soluble
 Palladacyclic Aqua Catalysts in Water
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              331
_journal_page_last               338
_journal_paper_doi               10.1021/om0503592
_journal_volume                  25
_journal_year                    2006
_chemical_formula_sum            'C18 H33 F6 O3 P3 Pd'
_chemical_formula_weight         610.77
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                95.359(8)
_cell_angle_beta                 95.705(7)
_cell_angle_gamma                99.059(6)
_cell_formula_units_Z            2
_cell_length_a                   8.821(1)
_cell_length_b                   11.261(2)
_cell_length_c                   13.800(2)
_cell_measurement_reflns_used    4783
_cell_measurement_temperature    223.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1338.7(3)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 14.62
_diffrn_measured_fraction_theta_full 0.9910
_diffrn_measured_fraction_theta_max 0.9910
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9979
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    0.930
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.78
_refine_diff_density_min         -0.55
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    refU
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5684
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.0012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.10000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1426
_reflns_number_gt                5100
_reflns_number_total             5684
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_original_sg_symbol_H-M      'P -1         '
_cod_original_formula_sum        'C18 H33 F6 O3 P3 Pd '
_cod_database_code               4063325
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-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_calc_flag
Pd(1) Pd 0.33598(3) 0.33380(2) 0.75161(2) 0.03980(9) Uani 1.00 d
P(1) P 0.23561(10) 0.50276(8) 0.80035(7) 0.0432(2) Uani 1.00 d
P(2) P 0.3670(1) 0.13440(8) 0.73482(7) 0.0450(2) Uani 1.00 d
P(3) P 0.3012(1) 0.2695(1) 0.36693(9) 0.0637(3) Uani 1.00 d
F(1) F 0.2462(8) 0.3474(8) 0.4481(4) 0.215(3) Uani 1.00 d
F(2) F 0.1350(6) 0.2308(7) 0.3173(5) 0.183(3) Uani 1.00 d
F(3) F 0.307(1) 0.1684(8) 0.4273(6) 0.264(5) Uani 1.00 d
F(4) F 0.3054(10) 0.3758(5) 0.2991(5) 0.176(3) Uani 1.00 d
F(5) F 0.4706(6) 0.3234(8) 0.4073(6) 0.227(3) Uani 1.00 d
F(6) F 0.3679(7) 0.1978(5) 0.2844(4) 0.148(2) Uani 1.00 d
O(1) O 0.4668(4) 0.3951(3) 0.6364(2) 0.0684(10) Uani 1.00 d
O(2) O 0.1593(4) 0.4710(2) 0.9003(2) 0.0608(8) Uani 1.00 d
O(3) O 0.3023(4) 0.0808(2) 0.8325(2) 0.0574(8) Uani 1.00 d
C(1) C 0.2329(4) 0.2770(3) 0.8635(3) 0.0421(8) Uani 1.00 d
C(2) C 0.2326(4) 0.1596(3) 0.8889(3) 0.0475(9) Uani 1.00 d
C(3) C 0.1665(5) 0.1204(4) 0.9698(3) 0.061(1) Uani 1.00 d
C(4) C 0.0972(6) 0.1999(4) 1.0261(3) 0.067(1) Uani 1.00 d
C(5) C 0.0940(5) 0.3160(4) 1.0032(3) 0.062(1) Uani 1.00 d
C(6) C 0.1617(4) 0.3532(3) 0.9224(3) 0.0487(9) Uani 1.00 d
C(7) C 0.0738(5) 0.5312(4) 0.7179(4) 0.066(1) Uani 1.00 d
C(8) C -0.0529(7) 0.4211(7) 0.6983(7) 0.123(3) Uani 1.00 d
C(9) C 0.1308(7) 0.5687(5) 0.6231(4) 0.081(2) Uani 1.00 d
C(10) C 0.3607(4) 0.6471(3) 0.8391(3) 0.0487(9) Uani 1.00 d
C(11) C 0.2780(7) 0.7456(4) 0.8812(4) 0.073(1) Uani 1.00 d
C(12) C 0.4959(7) 0.6283(5) 0.9100(5) 0.086(2) Uani 1.00 d
C(13) C 0.2397(5) 0.0412(4) 0.6336(3) 0.057(1) Uani 1.00 d
C(14) C 0.0788(7) 0.0679(6) 0.6379(5) 0.091(2) Uani 1.00 d
C(15) C 0.2458(8) -0.0927(4) 0.6319(4) 0.084(2) Uani 1.00 d
C(16) C 0.5574(5) 0.0915(4) 0.7377(4) 0.064(1) Uani 1.00 d
C(17) C 0.6272(7) 0.1214(6) 0.6449(5) 0.086(2) Uani 1.00 d
C(18) C 0.6608(9) 0.1548(8) 0.8298(5) 0.107(3) Uani 1.00 d
H(1) H 0.1686 0.0403 0.9858 0.06(1) Uiso 1.00 calc
H(2) H 0.0516 0.1742 1.0821 0.07(1) Uiso 1.00 calc
H(3) H 0.0464 0.3702 1.0425 0.11(1) Uiso 1.00 calc
H(4) H 0.0322 0.5960 0.7477 0.07(1) Uiso 1.00 calc
H(5) H -0.1390 0.4382 0.6587 0.10(1) Uiso 1.00 calc
H(6) H -0.0836 0.3965 0.7582 0.08(1) Uiso 1.00 calc
H(7) H -0.0145 0.3552 0.6642 0.13(1) Uiso 1.00 calc
H(8) H 0.0487 0.5907 0.5826 0.18(1) Uiso 1.00 calc
H(9) H 0.1676 0.5030 0.5897 0.09(1) Uiso 1.00 calc
H(10) H 0.2128 0.6358 0.6376 0.11(1) Uiso 1.00 calc
H(11) H 0.4036 0.6744 0.7830 0.07(1) Uiso 1.00 calc
H(12) H 0.1965 0.7566 0.8341 0.16(1) Uiso 1.00 calc
H(13) H 0.2370 0.7228 0.9389 0.08(1) Uiso 1.00 calc
H(14) H 0.3492 0.8194 0.8962 0.12(1) Uiso 1.00 calc
H(15) H 0.4561 0.5999 0.9686 0.15(1) Uiso 1.00 calc
H(16) H 0.5470 0.5683 0.8818 0.07(1) Uiso 1.00 calc
H(17) H 0.5648 0.7012 0.9285 0.09(1) Uiso 1.00 calc
H(18) H 0.2722 0.0664 0.5740 0.07(1) Uiso 1.00 calc
H(19) H 0.0419 0.0428 0.6980 0.07(1) Uiso 1.00 calc
H(20) H 0.0110 0.0247 0.5845 0.15(1) Uiso 1.00 calc
H(21) H 0.0783 0.1520 0.6384 0.13(1) Uiso 1.00 calc
H(22) H 0.2174 -0.1199 0.6918 0.11(1) Uiso 1.00 calc
H(23) H 0.1776 -0.1366 0.5788 0.09(1) Uiso 1.00 calc
H(24) H 0.3488 -0.1058 0.6248 0.07(1) Uiso 1.00 calc
H(25) H 0.5468 0.0065 0.7403 0.11(1) Uiso 1.00 calc
H(26) H 0.5618 0.0814 0.5894 0.18(1) Uiso 1.00 calc
H(27) H 0.7260 0.0974 0.6460 0.10(1) Uiso 1.00 calc
H(28) H 0.6398 0.2071 0.6421 0.07(1) Uiso 1.00 calc
H(29) H 0.6255 0.1255 0.8863 0.11(1) Uiso 1.00 calc
H(30) H 0.7647 0.1425 0.8255 0.13(1) Uiso 1.00 calc
H(31) H 0.6598 0.2406 0.8332 0.12(1) Uiso 1.00 calc
H(32) H 0.4762 0.4772 0.6235 0.12(1) Uiso 1.00 calc
H(33) H 0.4700 0.3841 0.5768 0.09(1) Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
F F 0.017 0.010
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
P P 0.102 0.094
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
Pd Pd -0.999 1.007
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
P(1) Pd(1) P(2) 158.98(4) yes
P(1) Pd(1) O(1) 101.71(9) yes
P(1) Pd(1) C(1) 80.2(1) yes
P(2) Pd(1) O(1) 98.53(9) yes
P(2) Pd(1) C(1) 80.1(1) yes
O(1) Pd(1) C(1) 175.2(1) yes
Pd(1) P(1) O(2) 104.5(1) yes
Pd(1) P(1) C(7) 114.8(1) yes
Pd(1) P(1) C(10) 121.0(1) yes
O(2) P(1) C(7) 104.2(2) yes
O(2) P(1) C(10) 102.8(2) yes
C(7) P(1) C(10) 107.5(2) yes
Pd(1) P(2) O(3) 104.26(10) yes
Pd(1) P(2) C(13) 114.1(1) yes
Pd(1) P(2) C(16) 121.6(2) yes
O(3) P(2) C(13) 103.1(2) yes
O(3) P(2) C(16) 102.7(2) yes
C(13) P(2) C(16) 108.6(2) yes
F(1) P(3) F(2) 90.9(4) yes
F(1) P(3) F(3) 92.5(5) yes
F(1) P(3) F(4) 90.6(4) yes
F(1) P(3) F(5) 89.4(4) yes
F(1) P(3) F(6) 175.6(4) yes
F(2) P(3) F(3) 98.2(5) yes
F(2) P(3) F(4) 84.1(4) yes
F(2) P(3) F(5) 171.7(5) yes
F(2) P(3) F(6) 92.4(4) yes
F(3) P(3) F(4) 176.0(4) yes
F(3) P(3) F(5) 90.1(6) yes
F(3) P(3) F(6) 89.7(4) yes
F(4) P(3) F(5) 87.5(5) yes
F(4) P(3) F(6) 86.9(3) yes
F(5) P(3) F(6) 86.9(4) yes
P(1) O(2) C(6) 114.3(2) yes
P(2) O(3) C(2) 114.6(2) yes
Pd(1) C(1) C(2) 121.5(3) yes
Pd(1) C(1) C(6) 121.4(3) yes
C(2) C(1) C(6) 117.1(3) yes
O(3) C(2) C(1) 119.0(3) yes
O(3) C(2) C(3) 119.0(3) yes
C(1) C(2) C(3) 122.0(3) yes
C(2) C(3) C(4) 118.7(4) yes
C(3) C(4) C(5) 121.2(3) yes
C(4) C(5) C(6) 119.0(4) yes
O(2) C(6) C(1) 119.2(3) yes
O(2) C(6) C(5) 118.7(3) yes
C(1) C(6) C(5) 122.1(4) yes
P(1) C(7) C(8) 111.0(4) yes
P(1) C(7) C(9) 109.6(3) yes
C(8) C(7) C(9) 111.2(5) yes
P(1) C(10) C(11) 114.2(3) yes
P(1) C(10) C(12) 109.4(3) yes
C(11) C(10) C(12) 111.7(4) yes
P(2) C(13) C(14) 108.4(3) yes
P(2) C(13) C(15) 113.4(3) yes
C(14) C(13) C(15) 112.3(5) yes
P(2) C(16) C(17) 109.7(3) yes
P(2) C(16) C(18) 110.1(4) yes
C(17) C(16) C(18) 111.7(5) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Pd(1) P(1) 2.2948(8) yes
Pd(1) P(2) 2.2977(8) yes
Pd(1) O(1) 2.158(3) yes
Pd(1) C(1) 1.975(4) yes
P(1) O(2) 1.639(3) yes
P(1) C(7) 1.824(4) yes
P(1) C(10) 1.817(4) yes
P(2) O(3) 1.645(3) yes
P(2) C(13) 1.832(4) yes
P(2) C(16) 1.817(4) yes
P(3) F(1) 1.523(4) yes
P(3) F(2) 1.533(5) yes
P(3) F(3) 1.475(5) yes
P(3) F(4) 1.586(5) yes
P(3) F(5) 1.549(6) yes
P(3) F(6) 1.551(4) yes
O(2) C(6) 1.391(4) yes
O(3) C(2) 1.381(4) yes
C(1) C(2) 1.399(5) yes
C(1) C(6) 1.391(5) yes
C(2) C(3) 1.386(5) yes
C(3) C(4) 1.384(6) yes
C(4) C(5) 1.378(6) yes
C(5) C(6) 1.384(5) yes
C(7) C(8) 1.517(7) yes
C(7) C(9) 1.520(8) yes
C(10) C(11) 1.523(6) yes
C(10) C(12) 1.520(7) yes
C(13) C(14) 1.502(8) yes
C(13) C(15) 1.516(6) yes
C(16) C(17) 1.519(8) yes
C(16) C(18) 1.533(8) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
F(1) O(1) 3.039(7) .
F(2) C(7) 3.525(8) 2_566
F(3) C(13) 3.368(6) .
F(3) C(17) 3.48(1) 2_656
F(4) O(1) 3.011(8) 2_666
F(4) C(8) 3.44(1) 2_566
F(4) C(12) 3.52(1) 2_666
F(5) O(1) 3.194(8) .
F(5) O(1) 3.25(1) 2_666
F(6) C(16) 3.416(6) 2_656
F(6) C(10) 3.426(7) 2_666
C(6) C(12) 3.582(7) 2_667
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O(1) H(33) F(1) 1_555 0.825 2.476 3.038(6) 126.388 no
O(1) H(33) F(5) 1_555 0.825 2.375 3.194(8) 172.044 no
O(1) H(32) F(4) 2_666 0.950 2.418 3.011(6) 120.239 no
O(1) H(32) F(5) 2_666 0.950 2.308 3.254(9) 173.376 no
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_publ_flag
Pd(1) P(1) O(2) C(6) -5.7(3) yes
Pd(1) P(1) C(7) C(8) 53.9(6) yes
Pd(1) P(1) C(7) C(9) -69.4(3) yes
Pd(1) P(1) C(10) C(11) -172.6(3) yes
Pd(1) P(1) C(10) C(12) -46.6(4) yes
Pd(1) P(2) O(3) C(2) 7.5(3) yes
Pd(1) P(2) C(13) C(14) -46.7(4) yes
Pd(1) P(2) C(13) C(15) -172.1(3) yes
Pd(1) P(2) C(16) C(17) -70.9(4) yes
Pd(1) P(2) C(16) C(18) 52.4(5) yes
Pd(1) C(1) C(2) O(3) -1.9(5) yes
Pd(1) C(1) C(2) C(3) 177.1(3) yes
Pd(1) C(1) C(6) O(2) 1.9(5) yes
Pd(1) C(1) C(6) C(5) -177.6(3) yes
P(1) Pd(1) P(2) O(3) -26.6(2) yes
P(1) Pd(1) P(2) C(13) 85.2(2) yes
P(1) Pd(1) P(2) C(16) -141.5(2) yes
P(1) Pd(1) C(1) C(2) 177.9(3) yes
P(1) Pd(1) C(1) C(6) -4.3(3) yes
P(1) O(2) C(6) C(1) 3.3(5) yes
P(1) O(2) C(6) C(5) -177.3(3) yes
P(2) Pd(1) P(1) O(2) 25.3(2) yes
P(2) Pd(1) P(1) C(7) -88.2(2) yes
P(2) Pd(1) P(1) C(10) 140.2(2) yes
P(2) Pd(1) C(1) C(2) 5.1(3) yes
P(2) Pd(1) C(1) C(6) -177.0(3) yes
P(2) O(3) C(2) C(1) -4.5(5) yes
P(2) O(3) C(2) C(3) 176.4(3) yes
O(1) Pd(1) P(1) O(2) -170.5(2) yes
O(1) Pd(1) P(1) C(7) 76.1(2) yes
O(1) Pd(1) P(1) C(10) -55.6(2) yes
O(1) Pd(1) P(2) O(3) 169.1(2) yes
O(1) Pd(1) P(2) C(13) -79.2(2) yes
O(1) Pd(1) P(2) C(16) 54.1(2) yes
O(1) Pd(1) C(1) C(2) -68(1) yes
O(1) Pd(1) C(1) C(6) 109(1) yes
O(2) P(1) Pd(1) C(1) 5.0(2) yes
O(2) P(1) C(7) C(8) -59.8(5) yes
O(2) P(1) C(7) C(9) 177.0(3) yes
O(2) P(1) C(10) C(11) -56.9(3) yes
O(2) P(1) C(10) C(12) 69.2(4) yes
O(2) C(6) C(1) C(2) 179.8(3) yes
O(2) C(6) C(5) C(4) -179.4(4) yes
O(3) P(2) Pd(1) C(1) -6.3(2) yes
O(3) P(2) C(13) C(14) 65.7(4) yes
O(3) P(2) C(13) C(15) -59.7(4) yes
O(3) P(2) C(16) C(17) 173.3(3) yes
O(3) P(2) C(16) C(18) -63.4(5) yes
O(3) C(2) C(1) C(6) -179.9(3) yes
O(3) C(2) C(3) C(4) 179.8(4) yes
C(1) Pd(1) P(1) C(7) -108.4(2) yes
C(1) Pd(1) P(1) C(10) 119.9(2) yes
C(1) Pd(1) P(2) C(13) 105.5(2) yes
C(1) Pd(1) P(2) C(16) -121.3(2) yes
C(1) C(2) C(3) C(4) 0.8(7) yes
C(1) C(6) C(5) C(4) 0.0(7) yes
C(2) O(3) P(2) C(13) -112.0(3) yes
C(2) O(3) P(2) C(16) 135.1(3) yes
C(2) C(1) C(6) C(5) 0.4(6) yes
C(2) C(3) C(4) C(5) -0.3(8) yes
C(3) C(2) C(1) C(6) -0.8(6) yes
C(3) C(4) C(5) C(6) 0.0(8) yes
C(6) O(2) P(1) C(7) 115.1(3) yes
C(6) O(2) P(1) C(10) -132.9(3) yes
C(7) P(1) C(10) C(11) 52.7(4) yes
C(7) P(1) C(10) C(12) 178.7(4) yes
C(8) C(7) P(1) C(10) -168.3(5) yes
C(9) C(7) P(1) C(10) 68.4(3) yes
C(13) P(2) C(16) C(17) 64.6(4) yes
C(13) P(2) C(16) C(18) -172.1(4) yes
C(14) C(13) P(2) C(16) 174.2(4) yes
C(15) C(13) P(2) C(16) 48.7(4) yes
C(15) C(13) P(2) C(16) 48.7(4) yes
