#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:08:04 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179314 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/11/4321163.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_4321163
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            'C34 H44 B2 F8 N2 O2 P2 Pd'
_chemical_formula_weight         854.67
_chemical_name_common            2a
_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                 97.789(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.9730(11)
_cell_length_b                   10.6282(7)
_cell_length_c                   19.7413(15)
_cell_measurement_reflns_used    27
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.48
_cell_measurement_theta_min      4.74
_cell_volume                     3736.2(4)
_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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6535
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.08
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  0.9496
_exptl_absorpt_correction_T_min  0.8690
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          .38
_exptl_crystal_size_mid          .54
_exptl_crystal_size_min          .42
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.0032(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   1.038
_refine_ls_goodness_of_fit_obs   1.075
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         5134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_restrained_S_obs      1.075
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_obs          0.0440
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0674P)²+3.8348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1236
_refine_ls_wR_factor_obs         0.1122
_reflns_number_observed          4342
_reflns_number_total             5459
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic990885j_3.cif
_cod_data_source_block           jhn183a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0674P)^2^+3.8348P] 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^)+(0.0674P)^2^+3.8348P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4321163
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 0.5000 0.58727(3) 0.2500 0.02992(11) Uani 1 d S .
P1 P 0.51725(4) 0.72877(6) 0.33191(3) 0.0302(2) Uani 1 d . .
O1 O 0.53483(13) 0.4413(2) 0.31892(11) 0.0423(5) Uani 1 d . .
N1 N 0.63482(15) 0.3550(3) 0.37972(13) 0.0427(6) Uani 1 d . .
C1 C 0.5247(2) 0.6435(3) 0.41344(13) 0.0350(6) Uani 1 d . .
H1A H 0.4807(2) 0.5935(3) 0.42103(13) 0.042 Uiso 1 calc R .
C2 C 0.5988(2) 0.5682(3) 0.41057(14) 0.0372(6) Uani 1 d . .
H2A H 0.6208(2) 0.5453(3) 0.45712(14) 0.045 Uiso 1 calc R .
C3 C 0.6532(2) 0.6611(3) 0.3795(2) 0.0420(7) Uani 1 d . .
H3A H 0.6994(2) 0.6719(3) 0.4106(2) 0.050 Uiso 1 calc R .
H3B H 0.6655(2) 0.6293(3) 0.3363(2) 0.050 Uiso 1 calc R .
C4 C 0.6103(2) 0.7876(3) 0.36884(15) 0.0369(6) Uani 1 d . .
H4A H 0.6328(2) 0.8509(3) 0.34170(15) 0.044 Uiso 1 calc R .
C5 C 0.5925(2) 0.8313(3) 0.4385(2) 0.0432(7) Uani 1 d . .
C6 C 0.5443(2) 0.7516(3) 0.46236(14) 0.0410(6) Uani 1 d . .
C7 C 0.6314(3) 0.9426(4) 0.4734(2) 0.0657(11) Uani 1 d . .
H7A H 0.6625(3) 0.9816(4) 0.4435(2) 0.099 Uiso 1 calc R .
H7B H 0.6620(3) 0.9158(4) 0.5145(2) 0.099 Uiso 1 calc R .
H7C H 0.5947(3) 1.0020(4) 0.4846(2) 0.099 Uiso 1 calc R .
C8 C 0.5130(3) 0.7554(4) 0.5286(2) 0.0668(11) Uani 1 d . .
H8A H 0.4799(3) 0.6852(4) 0.5311(2) 0.100 Uiso 1 calc R .
H8B H 0.4857(3) 0.8324(4) 0.5316(2) 0.100 Uiso 1 calc R .
H8C H 0.5534(3) 0.7510(4) 0.5658(2) 0.100 Uiso 1 calc R .
C9 C 0.4482(2) 0.8529(3) 0.32558(14) 0.0364(6) Uani 1 d . .
C10 C 0.3727(2) 0.8205(4) 0.3125(2) 0.0543(9) Uani 1 d . .
H10A H 0.3582(2) 0.7364(4) 0.3105(2) 0.065 Uiso 1 calc R .
C11 C 0.3190(2) 0.9156(5) 0.3025(3) 0.0712(12) Uani 1 d . .
H11A H 0.2683(2) 0.8951(5) 0.2934(3) 0.085 Uiso 1 calc R .
C12 C 0.3408(3) 1.0406(4) 0.3061(2) 0.0670(12) Uani 1 d . .
H12A H 0.3046(3) 1.1035(4) 0.2998(2) 0.080 Uiso 1 calc R .
C13 C 0.4147(3) 1.0721(3) 0.3188(2) 0.0594(10) Uani 1 d . .
H13A H 0.4288(3) 1.1563(3) 0.3213(2) 0.071 Uiso 1 calc R .
C14 C 0.4694(2) 0.9784(3) 0.3280(2) 0.0473(8) Uani 1 d . .
H14A H 0.5199(2) 1.0000(3) 0.3358(2) 0.057 Uiso 1 calc R .
C15 C 0.5875(2) 0.4510(3) 0.36770(14) 0.0353(6) Uani 1 d . .
C16 C 0.6961(2) 0.3494(4) 0.4373(2) 0.0665(11) Uani 1 d . .
H16A H 0.7228(2) 0.2715(4) 0.4356(2) 0.100 Uiso 1 calc R .
H16B H 0.6755(2) 0.3547(4) 0.4796(2) 0.100 Uiso 1 calc R .
H16C H 0.7299(2) 0.4184(4) 0.4342(2) 0.100 Uiso 1 calc R .
C17 C 0.6262(2) 0.2480(3) 0.3330(2) 0.0575(9) Uani 1 d . .
H17A H 0.6638(2) 0.1860(3) 0.3477(2) 0.086 Uiso 1 calc R .
H17B H 0.6318(2) 0.2758(3) 0.2877(2) 0.086 Uiso 1 calc R .
H17C H 0.5772(2) 0.2117(3) 0.3329(2) 0.086 Uiso 1 calc R .
B1 B 0.6838(3) 0.4645(5) 0.1351(3) 0.0664(13) Uani 1 d . .
F1 F 0.6522(2) 0.4982(5) 0.1929(2) 0.142(2) Uani 1 d . .
F2 F 0.7494(2) 0.5262(5) 0.1388(3) 0.154(2) Uani 1 d . .
F3 F 0.6995(3) 0.3473(4) 0.1381(4) 0.199(3) Uani 1 d . .
F4 F 0.6353(2) 0.4999(5) 0.0812(2) 0.144(2) Uani 1 d . .
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'
N N 0.0061 0.0033 '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'
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'
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
O1 Pd1 O1 84.86(11) 2_655 . ?
O1 Pd1 P1 91.66(6) 2_655 2_655 ?
O1 Pd1 P1 168.66(7) . 2_655 ?
O1 Pd1 P1 168.67(7) 2_655 . ?
O1 Pd1 P1 91.66(6) . . ?
P1 Pd1 P1 93.71(4) 2_655 . ?
C9 P1 C1 112.90(13) . . ?
C9 P1 C4 111.04(14) . . ?
C1 P1 C4 82.32(13) . . ?
C9 P1 Pd1 114.96(9) . . ?
C1 P1 Pd1 107.04(10) . . ?
C4 P1 Pd1 123.59(10) . . ?
C15 O1 Pd1 124.1(2) . . ?
C15 N1 C17 118.3(3) . . ?
C15 N1 C16 124.2(3) . . ?
C17 N1 C16 117.4(3) . . ?
C6 C1 C2 106.6(2) . . ?
C6 C1 P1 99.6(2) . . ?
C2 C1 P1 100.5(2) . . ?
C15 C2 C1 113.1(2) . . ?
C15 C2 C3 110.2(2) . . ?
C1 C2 C3 105.7(2) . . ?
C4 C3 C2 105.9(2) . . ?
C5 C4 C3 107.7(2) . . ?
C5 C4 P1 99.7(2) . . ?
C3 C4 P1 99.7(2) . . ?
C6 C5 C7 128.4(3) . . ?
C6 C5 C4 110.4(3) . . ?
C7 C5 C4 120.9(3) . . ?
C5 C6 C8 128.9(3) . . ?
C5 C6 C1 111.2(3) . . ?
C8 C6 C1 119.8(3) . . ?
C14 C9 C10 120.1(3) . . ?
C14 C9 P1 121.2(2) . . ?
C10 C9 P1 118.5(3) . . ?
C9 C10 C11 119.1(4) . . ?
C12 C11 C10 120.2(4) . . ?
C13 C12 C11 120.6(4) . . ?
C12 C13 C14 120.1(4) . . ?
C9 C14 C13 119.9(3) . . ?
O1 C15 N1 118.0(3) . . ?
O1 C15 C2 121.9(3) . . ?
N1 C15 C2 120.0(3) . . ?
F3 B1 F4 115.4(5) . . ?
F3 B1 F2 106.6(5) . . ?
F4 B1 F2 112.2(5) . . ?
F3 B1 F1 109.1(6) . . ?
F4 B1 F1 106.7(4) . . ?
F2 B1 F1 106.5(5) . . ?
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 O1 2.102(2) 2_655 ?
Pd1 O1 2.103(2) . ?
Pd1 P1 2.1991(7) 2_655 ?
Pd1 P1 2.1991(7) . ?
P1 C9 1.804(3) . ?
P1 C1 1.836(3) . ?
P1 C4 1.841(3) . ?
O1 C15 1.259(3) . ?
N1 C15 1.329(4) . ?
N1 C17 1.460(4) . ?
N1 C16 1.473(4) . ?
C1 C6 1.512(4) . ?
C1 C2 1.562(4) . ?
C2 C15 1.504(4) . ?
C2 C3 1.572(4) . ?
C3 C4 1.549(4) . ?
C4 C5 1.526(4) . ?
C5 C6 1.342(5) . ?
C5 C7 1.494(4) . ?
C6 C8 1.492(5) . ?
C9 C14 1.386(4) . ?
C9 C10 1.389(5) . ?
C10 C11 1.394(5) . ?
C11 C12 1.383(6) . ?
C12 C13 1.360(7) . ?
C13 C14 1.393(5) . ?
B1 F3 1.277(6) . ?
B1 F4 1.335(6) . ?
B1 F2 1.343(6) . ?
B1 F1 1.387(6) . ?
