#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:08:04 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179314 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/11/4321166.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_4321166
loop_
_publ_author_name
'Kent D. Redwine'
'William L. Wilson'
'Donald G. Moses'
'Vincent J. Catalano'
'John H. Nelson'
_publ_section_title
;
 Cooperative Diastereoselectivity of Palladium- and Platinum-Promoted
 Intramolecular [4+2] Diels-Alder Cycloaddition Reactions of
 3,4-Dimethyl-1-phenylphosphole
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3392
_journal_page_last               3402
_journal_paper_doi               10.1021/ic990885j
_journal_volume                  39
_journal_year                    2000
_chemical_formula_sum            'C61 H70 B2 F8 O3 P4 Pd'
_chemical_formula_weight         1255.07
_chemical_name_common            4a
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 95.341(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0801(9)
_cell_length_b                   26.660(2)
_cell_length_c                   19.2852(12)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.49
_cell_measurement_theta_min      5.34
_cell_volume                     6183.9(8)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       'ω 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  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0686
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6631
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.86
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.470
_exptl_absorpt_correction_T_max  0.9730
_exptl_absorpt_correction_T_min  0.9279
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .46
_exptl_crystal_size_min          .42
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.193
_refine_ls_extinction_coef       0.0030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.085
_refine_ls_goodness_of_fit_obs   1.155
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         4834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_restrained_S_obs      1.155
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_obs          0.0660
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1006P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1958
_refine_ls_wR_factor_obs         0.1579
_reflns_number_observed          3449
_reflns_number_total             5463
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic990885j_6.cif
_cod_data_source_block           jhn150a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1006P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1006P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        6183.8(7)
_cod_database_code               4321166
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Pd1 Pd 0.0000 0.38468(2) 0.2500 0.0420(3) Uani 1 d S .
P1 P 0.11189(12) 0.38180(6) 0.15726(8) 0.0483(4) Uani 1 d . .
P2 P -0.14026(12) 0.38333(6) 0.15722(7) 0.0462(4) Uani 1 d . .
C1 C 0.0285(5) 0.3575(3) 0.0788(3) 0.055(2) Uani 1 d . .
H1A H 0.0071(5) 0.3221(3) 0.0805(3) 0.065 Uiso 1 calc R .
C2 C -0.0673(5) 0.3955(2) 0.0792(3) 0.0498(15) Uani 1 d . .
H2A H -0.1180(5) 0.3932(2) 0.0366(3) 0.060 Uiso 1 calc R .
C3 C -0.0124(5) 0.4483(2) 0.0868(3) 0.055(2) Uani 1 d . .
H3A H -0.0406(5) 0.4668(2) 0.1248(3) 0.066 Uiso 1 calc R .
H3B H -0.0274(5) 0.4675(2) 0.0442(3) 0.066 Uiso 1 calc R .
C4 C 0.1149(5) 0.4383(2) 0.1021(3) 0.0523(15) Uani 1 d . .
H4A H 0.1598(5) 0.4664(2) 0.1216(3) 0.063 Uiso 1 calc R .
C5 C 0.1505(5) 0.4154(3) 0.0358(3) 0.059(2) Uani 1 d . .
C6 C 0.1028(6) 0.3714(3) 0.0226(3) 0.059(2) Uani 1 d . .
C7 C 0.2263(6) 0.4451(3) -0.0071(4) 0.078(2) Uani 1 d . .
H7A H 0.2474(6) 0.4758(3) 0.0166(4) 0.117 Uiso 1 calc R .
H7B H 0.1879(6) 0.4526(3) -0.0517(4) 0.117 Uiso 1 calc R .
H7C H 0.2916(6) 0.4257(3) -0.0133(4) 0.117 Uiso 1 calc R .
C8 C 0.1082(7) 0.3368(3) -0.0387(3) 0.081(2) Uani 1 d . .
H8A H 0.0638(7) 0.3075(3) -0.0324(3) 0.121 Uiso 1 calc R .
H8B H 0.1839(7) 0.3269(3) -0.0421(3) 0.121 Uiso 1 calc R .
H8C H 0.0804(7) 0.3538(3) -0.0806(3) 0.121 Uiso 1 calc R .
C9 C 0.2462(6) 0.3521(3) 0.1615(3) 0.065(2) Uani 1 d . .
C10 C 0.2516(8) 0.3005(4) 0.1592(4) 0.094(3) Uani 1 d . .
H10A H 0.1870(8) 0.2814(4) 0.1569(4) 0.112 Uiso 1 calc R .
C11 C 0.3562(11) 0.2772(5) 0.1603(5) 0.129(4) Uani 1 d . .
H11A H 0.3615(11) 0.2425(5) 0.1569(5) 0.155 Uiso 1 calc R .
C12 C 0.4490(11) 0.3059(7) 0.1664(6) 0.143(6) Uani 1 d . .
H12A H 0.5180(11) 0.2902(7) 0.1702(6) 0.171 Uiso 1 calc R .
C13 C 0.4452(8) 0.3567(7) 0.1673(6) 0.138(5) Uani 1 d . .
H13A H 0.5104(8) 0.3754(7) 0.1689(6) 0.165 Uiso 1 calc R .
C14 C 0.3443(6) 0.3802(4) 0.1658(4) 0.092(3) Uani 1 d . .
H14A H 0.3409(6) 0.4150(4) 0.1677(4) 0.110 Uiso 1 calc R .
C15 C -0.2520(5) 0.4294(2) 0.1547(3) 0.054(2) Uani 1 d . .
C16 C -0.2622(7) 0.4607(3) 0.2091(4) 0.086(2) Uani 1 d . .
H16A H -0.2112(7) 0.4587(3) 0.2482(4) 0.103 Uiso 1 calc R .
C17 C -0.3469(8) 0.4954(4) 0.2075(5) 0.112(3) Uani 1 d . .
H17A H -0.3524(8) 0.5167(4) 0.2452(5) 0.135 Uiso 1 calc R .
C18 C -0.4210(7) 0.4984(4) 0.1518(5) 0.097(3) Uani 1 d . .
H18A H -0.4807(7) 0.5204(4) 0.1520(5) 0.117 Uiso 1 calc R .
C19 C -0.4098(7) 0.4696(3) 0.0953(6) 0.094(3) Uani 1 d . .
H19A H -0.4590(7) 0.4734(3) 0.0556(6) 0.113 Uiso 1 calc R .
C20 C -0.3256(6) 0.4347(3) 0.0962(4) 0.083(2) Uani 1 d . .
H20A H -0.3184(6) 0.4147(3) 0.0574(4) 0.100 Uiso 1 calc R .
C21 C -0.2001(5) 0.3215(2) 0.1420(3) 0.056(2) Uani 1 d . .
C22 C -0.2717(6) 0.3108(3) 0.0853(4) 0.085(2) Uani 1 d . .
H22A H -0.2932(6) 0.3363(3) 0.0539(4) 0.102 Uiso 1 calc R .
C23 C -0.3135(7) 0.2629(4) 0.0733(5) 0.098(3) Uani 1 d . .
H23A H -0.3641(7) 0.2567(4) 0.0349(5) 0.117 Uiso 1 calc R .
C24 C -0.2810(8) 0.2247(3) 0.1175(5) 0.091(3) Uani 1 d . .
H24A H -0.3091(8) 0.1925(3) 0.1097(5) 0.109 Uiso 1 calc R .
C25 C -0.2088(10) 0.2342(3) 0.1713(5) 0.119(4) Uani 1 d . .
H25A H -0.1845(10) 0.2082(3) 0.2010(5) 0.143 Uiso 1 calc R .
C26 C -0.1681(8) 0.2827(3) 0.1847(4) 0.094(3) Uani 1 d . .
H26A H -0.1182(8) 0.2885(3) 0.2236(4) 0.113 Uiso 1 calc R .
B1 B -0.2606(16) 0.4213(5) -0.1135(7) 0.115(4) Uani 1 d . .
F1 F -0.2784(10) 0.3926(3) -0.0634(4) 0.214(5) Uani 1 d . .
F2 F -0.1548(9) 0.4314(5) -0.0924(7) 0.258(5) Uani 1 d . .
F3 F -0.2785(12) 0.3964(3) -0.1711(4) 0.247(6) Uani 1 d . .
F4 F -0.3060(7) 0.4648(3) -0.1193(5) 0.205(4) Uani 1 d . .
C29 C 0.0434(13) 0.1564(8) 0.0361(9) 0.217(8) Uani 1 d . .
H29A H 0.0488(13) 0.1212(8) 0.0461(9) 0.325 Uiso 1 calc R .
H29B H 0.0999(13) 0.1657(8) 0.0067(9) 0.325 Uiso 1 calc R .
H29C H -0.0285(13) 0.1637(8) 0.0127(9) 0.325 Uiso 1 calc R .
C30 C 0.0576(13) 0.1835(7) 0.0979(12) 0.169(7) Uani 1 d . .
C31 C 0.0553(14) 0.2244(5) 0.1012(13) 0.299(15) Uani 1 d . .
H31A H 0.0672(14) 0.2345(5) 0.1490(13) 0.448 Uiso 1 calc R .
H31B H -0.0159(14) 0.2362(5) 0.0816(13) 0.448 Uiso 1 calc R .
H31C H 0.1126(14) 0.2383(5) 0.0756(13) 0.448 Uiso 1 calc R .
O1 O 0.0745(17) 0.1489(10) 0.1611(8) 0.348(11) Uani 1 d . .
C32 C -0.0731(12) 0.5780(6) 0.1999(6) 0.177(6) Uani 1 d . .
H32A H -0.1173(12) 0.5558(6) 0.1695(6) 0.266 Uiso 1 calc R .
H32B H -0.0285(12) 0.5988(6) 0.1728(6) 0.266 Uiso 1 calc R .
H32C H -0.1209(12) 0.5988(6) 0.2247(6) 0.266 Uiso 1 calc R .
C33 C 0.0000 0.5484(6) 0.2500 0.112(5) Uani 1 d S .
O2 O 0.0000 0.5035(4) 0.2500 0.134(4) Uani 1 d S .
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
P1 Pd1 P1 176.24(9) . 2 ?
P1 Pd1 P2 81.04(5) . . ?
P1 Pd1 P2 98.90(5) 2 . ?
P1 Pd1 P2 98.90(5) . 2 ?
P1 Pd1 P2 81.04(5) 2 2 ?
P2 Pd1 P2 178.24(9) . 2 ?
C9 P1 C4 108.6(3) . . ?
C9 P1 C1 107.6(3) . . ?
C4 P1 C1 81.5(3) . . ?
C9 P1 Pd1 124.2(2) . . ?
C4 P1 Pd1 117.2(2) . . ?
C1 P1 Pd1 109.1(2) . . ?
C21 P2 C15 109.0(3) . . ?
C21 P2 C2 104.0(3) . . ?
C15 P2 C2 105.6(3) . . ?
C21 P2 Pd1 112.7(2) . . ?
C15 P2 Pd1 119.4(2) . . ?
C2 P2 Pd1 104.7(2) . . ?
C6 C1 C2 109.9(5) . . ?
C6 C1 P1 100.7(4) . . ?
C2 C1 P1 96.7(4) . . ?
C1 C2 C3 106.3(5) . . ?
C1 C2 P2 107.8(4) . . ?
C3 C2 P2 108.4(4) . . ?
C2 C3 C4 105.4(5) . . ?
C5 C4 C3 105.2(5) . . ?
C5 C4 P1 100.4(4) . . ?
C3 C4 P1 100.2(4) . . ?
C6 C5 C7 129.4(7) . . ?
C6 C5 C4 111.6(6) . . ?
C7 C5 C4 119.0(6) . . ?
C5 C6 C8 130.2(6) . . ?
C5 C6 C1 110.7(6) . . ?
C8 C6 C1 119.0(6) . . ?
C10 C9 C14 119.6(8) . . ?
C10 C9 P1 118.9(6) . . ?
C14 C9 P1 121.4(6) . . ?
C9 C10 C11 119.1(10) . . ?
C12 C11 C10 119.1(12) . . ?
C11 C12 C13 122.5(11) . . ?
C12 C13 C14 119.2(12) . . ?
C13 C14 C9 120.3(10) . . ?
C16 C15 C20 118.2(7) . . ?
C16 C15 P2 121.0(5) . . ?
C20 C15 P2 120.8(6) . . ?
C15 C16 C17 121.1(8) . . ?
C18 C17 C16 119.9(9) . . ?
C17 C18 C19 120.4(8) . . ?
C18 C19 C20 120.1(8) . . ?
C15 C20 C19 120.1(8) . . ?
C26 C21 C22 116.9(7) . . ?
C26 C21 P2 120.6(6) . . ?
C22 C21 P2 122.4(6) . . ?
C21 C22 C23 121.5(8) . . ?
C24 C23 C22 120.4(8) . . ?
C25 C24 C23 118.7(8) . . ?
C24 C25 C26 121.3(9) . . ?
C21 C26 C25 121.2(8) . . ?
F1 B1 F4 120.6(16) . . ?
F1 B1 F3 108.7(11) . . ?
F4 B1 F3 110.6(14) . . ?
F1 B1 F2 96.6(14) . . ?
F4 B1 F2 103.5(11) . . ?
F3 B1 F2 116.4(17) . . ?
C31 C30 C29 124.4(28) . . ?
C31 C30 O1 124.1(22) . . ?
C29 C30 O1 111.6(17) . . ?
O2 C33 C32 122.4(8) . 2 ?
O2 C33 C32 122.4(8) . . ?
C32 C33 C32 115.2(17) 2 . ?
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 2.3414(14) . ?
Pd1 P1 2.3414(14) 2 ?
Pd1 P2 2.3472(14) . ?
Pd1 P2 2.3473(14) 2 ?
P1 C9 1.801(7) . ?
P1 C4 1.846(6) . ?
P1 C1 1.855(6) . ?
P2 C21 1.812(7) . ?
P2 C15 1.822(6) . ?
P2 C2 1.841(6) . ?
C1 C6 1.516(8) . ?
C1 C2 1.539(9) . ?
C2 C3 1.557(8) . ?
C3 C4 1.562(8) . ?
C4 C5 1.515(8) . ?
C5 C6 1.322(9) . ?
C5 C7 1.513(9) . ?
C6 C8 1.505(9) . ?
C9 C10 1.376(11) . ?
C9 C14 1.398(10) . ?
C10 C11 1.407(13) . ?
C11 C12 1.35(2) . ?
C12 C13 1.35(2) . ?
C13 C14 1.368(13) . ?
C15 C16 1.355(9) . ?
C15 C20 1.377(9) . ?
C16 C17 1.378(10) . ?
C17 C18 1.335(12) . ?
C18 C19 1.351(12) . ?
C19 C20 1.377(11) . ?
C21 C26 1.357(9) . ?
C21 C22 1.360(9) . ?
C22 C23 1.387(11) . ?
C23 C24 1.361(12) . ?
C24 C25 1.316(12) . ?
C25 C26 1.399(11) . ?
B1 F1 1.265(13) . ?
B1 F4 1.28(2) . ?
B1 F3 1.293(14) . ?
B1 F2 1.33(2) . ?
C29 C30 1.39(2) . ?
C30 C31 1.09(2) . ?
C30 O1 1.53(2) . ?
C32 C33 1.477(13) . ?
C33 O2 1.20(2) . ?
C33 C32 1.477(13) 2 ?
