#------------------------------------------------------------------------------
#$Date: 2018-08-10 01:33:09 +0300 (Fri, 10 Aug 2018) $
#$Revision: 209531 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/33/4063366.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_4063366
loop_
_publ_author_name
'Kleimark, Jonatan'
'Johansson, Charlotte'
'Olsson, Susanne'
'Håkansson, Mikael'
'Hansson, Sverker'
'Åkermark, Björn'
'Norrby, Per-Ola'
_publ_contact_author_address
;Department of Chemistry,
University of Gothenburg,
SE-412 96 Göteborg,
Sweden
;
_publ_contact_author_email       pon@chem.gu.se
_publ_contact_author_fax         '+46 31 772 3840'
_publ_contact_author_name        'Per-Ola Norrby'
_publ_contact_author_phone       '+46 31 786 9034'
_publ_section_title
;
 Sterically Governed Selectivity in Palladium-Assisted Allylic Alkylation
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              230
_journal_paper_doi               10.1021/om1007264
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C30 H30 B F4 P Pd S'
_chemical_formula_sum            'C30 H30 B F4 P Pd S'
_chemical_formula_weight         646.78
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_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                 107.523(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.005(4)
_cell_length_b                   13.835(3)
_cell_length_c                   15.730(5)
_cell_measurement_reflns_used    9518
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.94
_cell_volume                     2906.4(14)
_computing_cell_refinement       'CrystalClear(Rigaku, 2000)'
_computing_data_collection       'CrystalClear(Rigaku, 2000)'
_computing_data_reduction        'CrystalClear(Rigaku, 2000)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-92
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 105
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Rigaku R-AXIS IIC image-plate system'
_diffrn_measurement_method       φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'rotating anode X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9518
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.94
_diffrn_source_type              RU-H3R
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         4999
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0442
_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)+(0.0922P)²+2.5724P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                4419
_reflns_number_total             4999
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om1007264_si_002.cif
_cod_data_source_block           2b
_cod_depositor_comments
;
 Removing duplicate rows from the ATOM_TYPE loop.

 Antanas Vaitkus,
 2018-08-10
;
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               4063366
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'
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
C1 C 1.0246(6) 0.7143(6) 0.3028(6) 0.085(3) Uani 1 1 d . . .
H1A H 1.0375 0.6558 0.2793 0.102 Uiso 1 1 calc R . .
H1B H 1.0286 0.7186 0.3628 0.102 Uiso 1 1 calc R . .
C2 C 0.9992(6) 0.7948(6) 0.2486(6) 0.086(3) Uani 1 1 d . . .
H2 H 0.9865 0.8528 0.2730 0.103 Uiso 1 1 calc R . .
C3 C 0.9924(6) 0.7917(6) 0.1595(6) 0.084(2) Uani 1 1 d . . .
H3 H 1.0129 0.7352 0.1381 0.101 Uiso 1 1 calc R . .
C7 C 0.6528(5) 0.6782(5) 0.0409(4) 0.0584(15) Uani 1 1 d . . .
C8 C 0.6135(6) 0.7386(6) 0.0931(5) 0.0745(19) Uani 1 1 d . . .
H8 H 0.6535 0.7840 0.1311 0.089 Uiso 1 1 calc R . .
C9 C 0.5108(7) 0.7289(8) 0.0865(7) 0.099(3) Uani 1 1 d . . .
H9 H 0.4830 0.7680 0.1210 0.119 Uiso 1 1 calc R . .
C10 C 0.4518(7) 0.6620(9) 0.0295(8) 0.110(3) Uani 1 1 d . . .
H10 H 0.3843 0.6564 0.0252 0.132 Uiso 1 1 calc R . .
C11 C 0.4928(7) 0.6033(8) -0.0213(8) 0.108(3) Uani 1 1 d . . .
H11 H 0.4529 0.5577 -0.0592 0.129 Uiso 1 1 calc R . .
C12 C 0.5916(6) 0.6116(6) -0.0163(5) 0.079(2) Uani 1 1 d . . .
H12 H 0.6181 0.5723 -0.0515 0.095 Uiso 1 1 calc R . .
C13 C 0.7219(4) 0.5988(4) 0.2890(4) 0.0472(13) Uani 1 1 d . . .
C14 C 0.7198(5) 0.6937(5) 0.3189(5) 0.0620(16) Uani 1 1 d . . .
H14 H 0.7756 0.7332 0.3276 0.074 Uiso 1 1 calc R . .
C15 C 0.6338(6) 0.7294(6) 0.3357(5) 0.076(2) Uani 1 1 d . . .
H15 H 0.6318 0.7930 0.3543 0.092 Uiso 1 1 calc R . .
C16 C 0.5533(6) 0.6711(7) 0.3247(6) 0.082(2) Uani 1 1 d . . .
H16 H 0.4971 0.6945 0.3378 0.098 Uiso 1 1 calc R . .
C17 C 0.5536(6) 0.5777(6) 0.2946(7) 0.085(2) Uani 1 1 d . . .
H17 H 0.4966 0.5395 0.2848 0.102 Uiso 1 1 calc R . .
C18 C 0.6385(5) 0.5403(5) 0.2788(5) 0.0669(18) Uani 1 1 d . . .
H18 H 0.6397 0.4762 0.2614 0.080 Uiso 1 1 calc R . .
C19 C 0.8011(4) 0.4414(4) 0.2109(4) 0.0492(13) Uani 1 1 d . . .
C20 C 0.8074(6) 0.3569(5) 0.2606(6) 0.078(2) Uani 1 1 d . . .
H20 H 0.8311 0.3599 0.3225 0.094 Uiso 1 1 calc R . .
C21 C 0.7794(6) 0.2699(5) 0.2198(8) 0.092(3) Uani 1 1 d . . .
H21 H 0.7846 0.2140 0.2537 0.111 Uiso 1 1 calc R . .
C22 C 0.7434(6) 0.2651(6) 0.1282(7) 0.086(3) Uani 1 1 d . . .
H22 H 0.7249 0.2056 0.1005 0.103 Uiso 1 1 calc R . .
C23 C 0.7347(8) 0.3460(7) 0.0780(7) 0.100(3) Uani 1 1 d . . .
H23 H 0.7092 0.3422 0.0163 0.120 Uiso 1 1 calc R . .
C24 C 0.7645(6) 0.4358(5) 0.1196(5) 0.0745(19) Uani 1 1 d . . .
H24 H 0.7593 0.4914 0.0852 0.089 Uiso 1 1 calc R . .
C25 C 0.9238(4) 0.5251(4) 0.3706(4) 0.0521(14) Uani 1 1 d . . .
C26 C 1.0171(5) 0.4917(5) 0.3698(5) 0.072(2) Uani 1 1 d . . .
H26 H 1.0315 0.4852 0.3161 0.087 Uiso 1 1 calc R . .
C27 C 1.0902(6) 0.4675(6) 0.4510(6) 0.085(3) Uani 1 1 d . . .
H27 H 1.1528 0.4455 0.4506 0.102 Uiso 1 1 calc R . .
C28 C 1.0693(7) 0.4764(6) 0.5296(6) 0.089(3) Uani 1 1 d . . .
H28 H 1.1175 0.4598 0.5827 0.107 Uiso 1 1 calc R . .
C29 C 0.9771(7) 0.5097(6) 0.5311(5) 0.084(2) Uani 1 1 d . . .
H29 H 0.9638 0.5165 0.5853 0.101 Uiso 1 1 calc R . .
C30 C 0.9035(5) 0.5336(5) 0.4518(5) 0.0683(18) Uani 1 1 d . . .
H30 H 0.8411 0.5551 0.4532 0.082 Uiso 1 1 calc R . .
F2A F 0.237(2) 0.4099(18) 0.2267(16) 0.166(9) Uiso 0.418(12) 1 d P A 1
F3A F 0.1565(9) 0.4482(16) 0.2340(7) 0.104(6) Uani 0.418(12) 1 d P A 1
F1A F 0.2911(10) 0.5208(13) 0.1917(9) 0.108(5) Uani 0.418(12) 1 d P A 1
F4A F 0.263(3) 0.548(3) 0.317(2) 0.28(3) Uani 0.418(12) 1 d P A 1
F2B F 0.2686(8) 0.4341(9) 0.3547(8) 0.141(5) Uani 0.582(12) 1 d P A 2
F3B F 0.1750(9) 0.5441(13) 0.2491(9) 0.130(5) Uani 0.582(12) 1 d P A 2
F4B F 0.3320(10) 0.5440(11) 0.3036(13) 0.169(8) Uani 0.582(12) 1 d P A 2
F1B F 0.3022(17) 0.426(2) 0.238(2) 0.31(2) Uani 0.582(12) 1 d P A 2
P1 P 0.83451(10) 0.55840(9) 0.26489(9) 0.0424(3) Uani 1 1 d . . .
S1 S 0.78061(13) 0.68464(14) 0.04419(12) 0.0630(4) Uani 1 1 d . . .
Pd1 Pd 0.89198(2) 0.68067(3) 0.19033(2) 0.04930(13) Uani 1 1 d . . .
B1 B 0.2547(9) 0.4862(9) 0.2673(8) 0.095(4) Uani 1 1 d . . .
C6 C 0.7843(7) 0.8066(8) 0.0001(7) 0.113(4) Uani 1 1 d . . .
H6A H 0.7425 0.8082 -0.0615 0.136 Uiso 1 1 calc R . .
H6B H 0.7560 0.8514 0.0334 0.136 Uiso 1 1 calc R . .
C5 C 0.8872(8) 0.8407(8) 0.0042(7) 0.116(4) Uani 1 1 d . . .
H5A H 0.8803 0.8951 -0.0361 0.139 Uiso 1 1 calc R . .
H5B H 0.9203 0.7893 -0.0180 0.139 Uiso 1 1 calc R . .
C4 C 0.9550(7) 0.8711(8) 0.0952(7) 0.100(3) Uani 1 1 d . . .
H4A H 1.0121 0.9052 0.0870 0.120 Uiso 1 1 calc R . .
H4B H 0.9186 0.9164 0.1211 0.120 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'
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'
S S 0.1246 0.1234 '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'
B B 0.0013 0.0007 '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
C2 C1 Pd1 71.1(4) . . ?
C3 C2 C1 121.9(9) . . ?
C3 C2 Pd1 73.8(4) . . ?
C1 C2 Pd1 72.1(4) . . ?
C2 C3 C4 125.1(9) . . ?
C2 C3 Pd1 69.9(4) . . ?
C4 C3 Pd1 122.9(6) . . ?
C12 C7 C8 120.1(7) . . ?
C12 C7 S1 118.2(6) . . ?
C8 C7 S1 121.7(5) . . ?
C7 C8 C9 118.2(8) . . ?
C10 C9 C8 120.5(10) . . ?
C9 C10 C11 120.0(9) . . ?
C12 C11 C10 120.5(9) . . ?
C11 C12 C7 120.7(9) . . ?
C18 C13 C14 118.9(6) . . ?
C18 C13 P1 123.3(5) . . ?
C14 C13 P1 117.8(5) . . ?
C13 C14 C15 120.2(7) . . ?
C16 C15 C14 119.8(7) . . ?
C15 C16 C17 121.0(7) . . ?
C16 C17 C18 120.2(7) . . ?
C17 C18 C13 119.9(7) . . ?
C24 C19 C20 118.7(6) . . ?
C24 C19 P1 120.0(5) . . ?
C20 C19 P1 121.2(5) . . ?
C21 C20 C19 120.9(8) . . ?
C20 C21 C22 119.9(8) . . ?
C23 C22 C21 120.6(7) . . ?
C22 C23 C24 119.8(8) . . ?
C19 C24 C23 120.0(7) . . ?
C26 C25 C30 119.2(6) . . ?
C26 C25 P1 117.8(5) . . ?
C30 C25 P1 123.0(5) . . ?
C25 C26 C27 119.8(8) . . ?
C28 C27 C26 120.3(7) . . ?
C27 C28 C29 120.3(7) . . ?
C28 C29 C30 120.4(8) . . ?
C25 C30 C29 120.0(7) . . ?
B1 F2A F3A 69.1(18) . . ?
F2A F3A B1 53.6(12) . . ?
C25 P1 C13 106.8(3) . . ?
C25 P1 C19 102.2(3) . . ?
C13 P1 C19 104.7(3) . . ?
C25 P1 Pd1 113.4(2) . . ?
C13 P1 Pd1 109.50(18) . . ?
C19 P1 Pd1 119.2(2) . . ?
C7 S1 C6 100.3(4) . . ?
C7 S1 Pd1 113.1(2) . . ?
C6 S1 Pd1 107.7(3) . . ?
C2 Pd1 C1 36.8(3) . . ?
C2 Pd1 C3 36.3(3) . . ?
C1 Pd1 C3 66.0(3) . . ?
C2 Pd1 P1 127.7(2) . . ?
C1 Pd1 P1 94.9(2) . . ?
C3 Pd1 P1 160.5(2) . . ?
C2 Pd1 S1 124.2(2) . . ?
C1 Pd1 S1 158.7(2) . . ?
C3 Pd1 S1 92.7(2) . . ?
P1 Pd1 S1 106.24(6) . . ?
F4A B1 F2A 166(3) . . ?
F4A B1 F1B 144(3) . . ?
F2A B1 F1B 43.5(13) . . ?
F4A B1 F4B 50(2) . . ?
F2A B1 F4B 139(2) . . ?
F1B B1 F4B 96.0(17) . . ?
F4A B1 F3B 66(2) . . ?
F2A B1 F3B 112.3(18) . . ?
F1B B1 F3B 146(2) . . ?
F4B B1 F3B 104.6(13) . . ?
F4A B1 F3A 115(2) . . ?
F2A B1 F3A 57.3(16) . . ?
F1B B1 F3A 100.7(15) . . ?
F4B B1 F3A 163.0(15) . . ?
F3B B1 F3A 59.1(10) . . ?
F4A B1 F1A 108(2) . . ?
F2A B1 F1A 85.9(16) . . ?
F1B B1 F1A 64.5(18) . . ?
F4B B1 F1A 73.9(12) . . ?
F3B B1 F1A 95.7(11) . . ?
F3A B1 F1A 110.4(9) . . ?
F4A B1 F2B 77(2) . . ?
F2A B1 F2B 90.8(15) . . ?
F1B B1 F2B 95(2) . . ?
F4B B1 F2B 91.7(10) . . ?
F3B B1 F2B 110.6(12) . . ?
F3A B1 F2B 90.2(11) . . ?
F1A B1 F2B 152.6(11) . . ?
C5 C6 S1 114.2(7) . . ?
C6 C5 C4 116.6(9) . . ?
C3 C4 C5 115.5(9) . . ?
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
C1 C2 1.382(11) . ?
C1 Pd1 2.194(7) . ?
C2 C3 1.375(12) . ?
C2 Pd1 2.182(7) . ?
C3 C4 1.479(12) . ?
C3 Pd1 2.232(7) . ?
C7 C12 1.388(10) . ?
C7 C8 1.396(10) . ?
C7 S1 1.777(7) . ?
C8 C9 1.416(11) . ?
C9 C10 1.378(15) . ?
C10 C11 1.379(15) . ?
C11 C12 1.367(12) . ?
C13 C18 1.390(8) . ?
C13 C14 1.397(8) . ?
C13 P1 1.818(6) . ?
C14 C15 1.399(10) . ?
C15 C16 1.354(11) . ?
C16 C17 1.377(11) . ?
C17 C18 1.385(10) . ?
C19 C24 1.374(9) . ?
C19 C20 1.394(9) . ?
C19 P1 1.823(6) . ?
C20 C21 1.365(11) . ?
C21 C22 1.377(13) . ?
C22 C23 1.354(13) . ?
C23 C24 1.408(10) . ?
C25 C26 1.390(9) . ?
C25 C30 1.394(9) . ?
C25 P1 1.814(6) . ?
C26 C27 1.415(11) . ?
C27 C28 1.359(12) . ?
C28 C29 1.378(13) . ?
C29 C30 1.398(10) . ?
F2A B1 1.22(3) . ?
F2A F3A 1.28(3) . ?
F3A B1 1.416(17) . ?
F1A B1 1.505(19) . ?
F4A B1 1.14(3) . ?
F2B B1 1.513(17) . ?
F3B B1 1.333(14) . ?
F4B B1 1.330(17) . ?
F1B B1 1.236(18) . ?
P1 Pd1 2.3353(14) . ?
S1 C6 1.831(9) . ?
S1 Pd1 2.3583(18) . ?
C6 C5 1.498(12) . ?
C5 C4 1.520(15) . ?
