#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:11:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178461 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/82/4028229.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_4028229
loop_
_publ_author_name
'Steven M. Raders'
'Jane N. Moore'
'Jacquelynn K. Parks'
'Ashley D. Miller'
'Thomas M. Leißing'
'Steven P. Kelley'
'Robin D. Rogers'
'Kevin H. Shaughnessy'
_publ_contact_author_address
;Department of Chemistry
Box 870336
The University of Alabama
Tuscaloosa, AL 35487-0336
USA
;
_publ_contact_author_email       kshaughn@as.ua.edu
_publ_contact_author_fax         205-348-9104
_publ_contact_author_name        'Kevin H. Shaughnessy'
_publ_contact_author_phone       205-348-4435
_publ_section_title
;
 Trineopentylphosphine: A Conformationally Flexible Ligand for the
 Coupling of Sterically Demanding Substrates in the Buchwald-Hartwig
 Amination and Suzuki-Miyaura Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4649
_journal_page_last               4664
_journal_paper_doi               10.1021/jo400435z
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C25 H46 Br P Pd'
_chemical_formula_weight         563.90
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 113.961(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0300(16)
_cell_length_b                   16.4173(16)
_cell_length_c                   12.3394(12)
_cell_measurement_reflns_used    4394
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.92
_cell_measurement_theta_min      2.19
_cell_volume                     2782.4(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.1054
_diffrn_reflns_av_sigmaI/netI    0.0741
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32865
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    2.169
_exptl_absorpt_correction_T_max  0.9579
_exptl_absorpt_correction_T_min  0.7094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      0
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.930
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         5711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0433
_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)+(0.0535P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                3584
_reflns_number_total             5711
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400435z_si_002_2.cif
_cod_data_source_block           8
_cod_database_code               4028229
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Pd Pd 0.39936(3) 0.47814(2) 0.35420(3) 0.03011(12) Uani 1 1 d .
Br Br 0.54532(4) 0.56904(3) 0.42715(5) 0.04689(18) Uani 1 1 d .
P1 P 0.27302(9) 0.39135(7) 0.29036(11) 0.0281(3) Uani 1 1 d .
C1 C 0.3586(3) 0.5255(3) 0.1915(4) 0.0267(10) Uani 1 1 d .
C2 C 0.3866(4) 0.4934(3) 0.1067(4) 0.0370(12) Uani 1 1 d .
H2A H 0.4246 0.4451 0.1234 0.044 Uiso 1 1 calc R
C3 C 0.3599(4) 0.5311(3) -0.0030(4) 0.0415(13) Uani 1 1 d .
H3A H 0.3807 0.5079 -0.0594 0.050 Uiso 1 1 calc R
C4 C 0.3041(3) 0.6012(3) -0.0329(4) 0.0331(11) Uani 1 1 d .
C5 C 0.2790(4) 0.6338(3) 0.0541(4) 0.0381(12) Uani 1 1 d .
H5A H 0.2419 0.6826 0.0379 0.046 Uiso 1 1 calc R
C6 C 0.3066(4) 0.5972(3) 0.1645(4) 0.0368(12) Uani 1 1 d .
H6A H 0.2892 0.6223 0.2226 0.044 Uiso 1 1 calc R
C7 C 0.2681(4) 0.6371(3) -0.1585(4) 0.0432(13) Uani 1 1 d .
C8 C 0.3508(5) 0.6435(4) -0.1992(5) 0.0687(19) Uani 1 1 d .
H8A H 0.3794 0.5895 -0.1967 0.103 Uiso 1 1 calc R
H8B H 0.4008 0.6806 -0.1465 0.103 Uiso 1 1 calc R
H8C H 0.3256 0.6646 -0.2805 0.103 Uiso 1 1 calc R
C9 C 0.1903(5) 0.5802(4) -0.2425(5) 0.068(2) Uani 1 1 d .
H9A H 0.2184 0.5260 -0.2401 0.102 Uiso 1 1 calc R
H9B H 0.1665 0.6018 -0.3235 0.102 Uiso 1 1 calc R
H9C H 0.1361 0.5763 -0.2179 0.102 Uiso 1 1 calc R
C10 C 0.2231(5) 0.7226(4) -0.1662(6) 0.074(2) Uani 1 1 d .
H10A H 0.1645 0.7186 -0.1502 0.111 Uiso 1 1 calc R
H10B H 0.2059 0.7450 -0.2458 0.111 Uiso 1 1 calc R
H10C H 0.2705 0.7585 -0.1074 0.111 Uiso 1 1 calc R
C11 C 0.1965(3) 0.3859(3) 0.1295(4) 0.0352(11) Uani 1 1 d .
H11A H 0.1738 0.4423 0.1053 0.042 Uiso 1 1 calc R
H11B H 0.2418 0.3731 0.0919 0.042 Uiso 1 1 calc R
C12 C 0.1055(4) 0.3307(3) 0.0652(5) 0.0472(14) Uani 1 1 d .
C13 C 0.1110(5) 0.2445(4) 0.1162(6) 0.071(2) Uani 1 1 d .
H13A H 0.0556 0.2123 0.0632 0.107 Uiso 1 1 calc R
H13B H 0.1093 0.2479 0.1946 0.107 Uiso 1 1 calc R
H13C H 0.1718 0.2184 0.1234 0.107 Uiso 1 1 calc R
C14 C 0.0125(4) 0.3722(4) 0.0592(6) 0.0658(18) Uani 1 1 d .
H14A H -0.0443 0.3408 0.0073 0.099 Uiso 1 1 calc R
H14B H 0.0089 0.4274 0.0275 0.099 Uiso 1 1 calc R
H14C H 0.0133 0.3750 0.1390 0.099 Uiso 1 1 calc R
C15 C 0.0977(5) 0.3224(4) -0.0630(5) 0.0678(19) Uani 1 1 d .
H15A H 0.0391 0.2914 -0.1104 0.102 Uiso 1 1 calc R
H15B H 0.1552 0.2939 -0.0623 0.102 Uiso 1 1 calc R
H15C H 0.0939 0.3767 -0.0976 0.102 Uiso 1 1 calc R
C16 C 0.3200(4) 0.2882(3) 0.3426(4) 0.0342(12) Uani 1 1 d .
H16A H 0.3434 0.2887 0.4300 0.041 Uiso 1 1 calc R
H16B H 0.2636 0.2508 0.3123 0.041 Uiso 1 1 calc R
C17 C 0.4018(4) 0.2486(3) 0.3136(5) 0.0467(14) Uani 1 1 d .
C18 C 0.4034(5) 0.1582(3) 0.3459(6) 0.073(2) Uani 1 1 d .
H18A H 0.4580 0.1311 0.3365 0.109 Uiso 1 1 calc R
H18B H 0.3422 0.1325 0.2935 0.109 Uiso 1 1 calc R
H18C H 0.4111 0.1532 0.4284 0.109 Uiso 1 1 calc R
C19 C 0.3860(5) 0.2563(3) 0.1843(5) 0.0617(18) Uani 1 1 d .
H19A H 0.4359 0.2249 0.1706 0.093 Uiso 1 1 calc R
H19B H 0.3905 0.3138 0.1655 0.093 Uiso 1 1 calc R
H19C H 0.3214 0.2353 0.1336 0.093 Uiso 1 1 calc R
C20 C 0.5023(5) 0.2851(4) 0.3891(6) 0.0675(19) Uani 1 1 d .
H20A H 0.5527 0.2546 0.3752 0.101 Uiso 1 1 calc R
H20B H 0.5143 0.2817 0.4732 0.101 Uiso 1 1 calc R
H20C H 0.5039 0.3423 0.3671 0.101 Uiso 1 1 calc R
C21 C 0.1940(3) 0.4073(3) 0.3695(4) 0.0348(12) Uani 1 1 d .
H21A H 0.1363 0.3720 0.3309 0.042 Uiso 1 1 calc R
H21B H 0.2296 0.3860 0.4509 0.042 Uiso 1 1 calc R
C22 C 0.1558(4) 0.4928(3) 0.3819(5) 0.0402(13) Uani 1 1 d .
C23 C 0.1035(5) 0.5356(4) 0.2642(5) 0.0612(17) Uani 1 1 d .
H23A H 0.1485 0.5432 0.2256 0.092 Uiso 1 1 calc R
H23B H 0.0803 0.5889 0.2776 0.092 Uiso 1 1 calc R
H23C H 0.0480 0.5026 0.2131 0.092 Uiso 1 1 calc R
C24 C 0.2378(4) 0.5485(3) 0.4635(5) 0.0518(15) Uani 1 1 d .
H24A H 0.2821 0.5613 0.4255 0.078 Uiso 1 1 calc R
H24B H 0.2739 0.5208 0.5391 0.078 Uiso 1 1 calc R
H24C H 0.2097 0.5991 0.4781 0.078 Uiso 1 1 calc R
C25 C 0.0838(4) 0.4799(4) 0.4404(6) 0.0589(16) Uani 1 1 d .
H25A H 0.0319 0.4428 0.3917 0.088 Uiso 1 1 calc R
H25B H 0.0554 0.5323 0.4473 0.088 Uiso 1 1 calc R
H25C H 0.1183 0.4563 0.5195 0.088 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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_3
C1 Pd P1 91.35(13) .
C1 Pd Br 89.77(12) .
P1 Pd Br 177.26(4) .
C1 Pd Br 174.50(13) 3_666
P1 Pd Br 92.50(3) 3_666
Br Pd Br 86.56(2) 3_666
Pd Br Pd 93.44(2) 3_666
C21 P1 C16 100.6(2) .
C21 P1 C11 108.9(2) .
C16 P1 C11 108.3(2) .
C21 P1 Pd 111.09(16) .
C16 P1 Pd 108.07(16) .
C11 P1 Pd 118.45(16) .
C6 C1 C2 117.4(4) .
C6 C1 Pd 119.2(3) .
C2 C1 Pd 123.2(3) .
C1 C2 C3 120.7(4) .
C4 C3 C2 122.3(5) .
C3 C4 C5 116.3(4) .
C3 C4 C7 121.0(4) .
C5 C4 C7 122.6(4) .
C4 C5 C6 121.9(4) .
C1 C6 C5 121.3(4) .
C8 C7 C9 108.8(5) .
C8 C7 C4 111.0(4) .
C9 C7 C4 108.0(4) .
C8 C7 C10 108.2(5) .
C9 C7 C10 108.6(5) .
C4 C7 C10 112.1(4) .
C12 C11 P1 127.5(4) .
C14 C12 C13 109.0(5) .
C14 C12 C15 107.6(5) .
C13 C12 C15 107.9(5) .
C14 C12 C11 111.1(4) .
C13 C12 C11 115.8(4) .
C15 C12 C11 104.9(5) .
C17 C16 P1 121.9(3) .
C19 C17 C18 109.4(5) .
C19 C17 C20 107.5(5) .
C18 C17 C20 108.1(5) .
C19 C17 C16 113.9(4) .
C18 C17 C16 106.0(4) .
C20 C17 C16 111.8(4) .
C22 C21 P1 121.9(3) .
C23 C22 C24 108.5(5) .
C23 C22 C25 108.9(5) .
C24 C22 C25 107.7(4) .
C23 C22 C21 113.3(4) .
C24 C22 C21 111.9(4) .
C25 C22 C21 106.4(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd C1 2.002(4) .
Pd P1 2.2453(12) .
Pd Br 2.4992(6) .
Pd Br 2.5978(7) 3_666
Br Pd 2.5978(6) 3_666
P1 C21 1.837(5) .
P1 C16 1.847(4) .
P1 C11 1.849(5) .
C1 C6 1.378(6) .
C1 C2 1.382(6) .
C2 C3 1.391(7) .
C3 C4 1.382(7) .
C4 C5 1.381(7) .
C4 C7 1.537(6) .
C5 C6 1.389(6) .
C7 C8 1.523(7) .
C7 C9 1.526(7) .
C7 C10 1.544(8) .
C11 C12 1.562(7) .
C12 C14 1.530(8) .
C12 C13 1.537(8) .
C12 C15 1.544(8) .
C16 C17 1.555(7) .
C17 C19 1.519(7) .
C17 C18 1.535(7) .
C17 C20 1.538(8) .
C21 C22 1.547(6) .
C22 C23 1.515(7) .
C22 C24 1.538(7) .
C22 C25 1.539(7) .
