#------------------------------------------------------------------------------
#$Date: 2019-11-25 17:15:46 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241426 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/11/4131143.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_4131143
loop_
_publ_author_name
'Lee, Sarah Yunmi'
'Hartwig, John F.'
_publ_section_title
;
 Palladium-Catalyzed, Site-Selective Direct Allylation of Aryl C-H Bonds
 by Silver-Mediated C-H Activation: A Synthetic and Mechanistic
 Investigation.
;
_journal_issue                   46
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15278
_journal_page_last               15284
_journal_paper_doi               10.1021/jacs.6b10220
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C30 H50 O2 P2 Pd'
_chemical_formula_weight         611.04
_chemical_name_common            sy3-052
_chemical_name_systematic        hartwig115
_space_group.centring_type       primitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 108.162(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5173(3)
_cell_length_b                   24.0717(9)
_cell_length_c                   8.7398(3)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.59
_cell_volume                     1502.71(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19233
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.374
_diffrn_reflns_theta_min         1.692
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       prism
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.818
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0258
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0188P)²+1.3387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0593
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2512
_reflns_number_total             2753
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b10220_si_003.cif
_cod_data_source_block           hartwig115
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4131143
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.971
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.8608(3) 0.59289(8) 0.5838(2) 0.0117(4) Uani 1 1 d . . .
C2 C 0.9620(3) 0.64811(8) 0.6368(2) 0.0144(4) Uani 1 1 d . . .
H2A H 0.9979 0.6513 0.7543 0.022 Uiso 1 1 calc R U .
H2B H 0.8785 0.6789 0.5874 0.022 Uiso 1 1 calc R U .
H2C H 1.0744 0.6496 0.6028 0.022 Uiso 1 1 calc R U .
C3 C 0.8123(3) 0.58856(9) 0.3995(2) 0.0143(4) Uani 1 1 d . . .
H3A H 0.9271 0.5916 0.3695 0.021 Uiso 1 1 calc R U .
H3B H 0.7264 0.6187 0.3485 0.021 Uiso 1 1 calc R U .
H3C H 0.7524 0.5527 0.3632 0.021 Uiso 1 1 calc R U .
C4 C 0.9903(3) 0.54446(9) 0.6603(2) 0.0146(4) Uani 1 1 d . . .
H4A H 1.0992 0.5445 0.6214 0.022 Uiso 1 1 calc R U .
H4B H 0.9223 0.5093 0.6308 0.022 Uiso 1 1 calc R U .
H4C H 1.0322 0.5486 0.7777 0.022 Uiso 1 1 calc R U .
C5 C 0.6683(3) 0.58061(9) 0.8506(2) 0.0130(4) Uani 1 1 d . . .
C6 C 0.6950(3) 0.51928(9) 0.9032(3) 0.0177(5) Uani 1 1 d . . .
H6A H 0.8098 0.5049 0.8871 0.027 Uiso 1 1 calc R U .
H6B H 0.5876 0.4975 0.8388 0.027 Uiso 1 1 calc R U .
H6C H 0.7046 0.5164 1.0174 0.027 Uiso 1 1 calc R U .
C7 C 0.4855(3) 0.60111(9) 0.8736(3) 0.0176(5) Uani 1 1 d . . .
H7A H 0.4895 0.5950 0.9856 0.026 Uiso 1 1 calc R U .
H7B H 0.3798 0.5806 0.8015 0.026 Uiso 1 1 calc R U .
H7C H 0.4701 0.6408 0.8486 0.026 Uiso 1 1 calc R U .
C8 C 0.8326(3) 0.61367(9) 0.9603(2) 0.0158(5) Uani 1 1 d . . .
H8A H 0.8192 0.6529 0.9288 0.024 Uiso 1 1 calc R U .
H8B H 0.9502 0.5992 0.9501 0.024 Uiso 1 1 calc R U .
H8C H 0.8336 0.6101 1.0722 0.024 Uiso 1 1 calc R U .
C9 C 0.4876(3) 0.64164(8) 0.5333(2) 0.0112(4) Uani 1 1 d . . .
C10 C 0.3453(3) 0.63028(9) 0.3898(2) 0.0143(4) Uani 1 1 d . . .
H10 H 0.3262 0.5930 0.3528 0.017 Uiso 1 1 calc R U .
C11 C 0.2313(3) 0.67157(9) 0.2998(3) 0.0180(5) Uani 1 1 d . . .
H11 H 0.1375 0.6626 0.2016 0.022 Uiso 1 1 calc R U .
C12 C 0.2552(3) 0.72589(9) 0.3539(3) 0.0195(5) Uani 1 1 d . . .
H12 H 0.1773 0.7544 0.2929 0.023 Uiso 1 1 calc R U .
C13 C 0.3921(3) 0.73880(9) 0.4962(3) 0.0168(5) Uani 1 1 d . . .
H13 H 0.4071 0.7761 0.5339 0.020 Uiso 1 1 calc R U .
C14 C 0.5079(3) 0.69738(8) 0.5844(2) 0.0126(4) Uani 1 1 d . . .
C15 C 0.7068(3) 0.76459(9) 0.7579(3) 0.0204(5) Uani 1 1 d . . .
H15A H 0.7313 0.7805 0.6633 0.031 Uiso 1 1 calc R U .
H15B H 0.8214 0.7659 0.8501 0.031 Uiso 1 1 calc R U .
H15C H 0.6083 0.7860 0.7826 0.031 Uiso 1 1 calc R U .
O1 O 0.6475(2) 0.70814(6) 0.72535(17) 0.0162(3) Uani 1 1 d . . .
P1 P 0.63195(7) 0.58090(2) 0.62541(6) 0.00933(12) Uani 1 1 d . . .
Pd1 Pd 0.5000 0.5000 0.5000 0.01178(8) Uani 1 2 d S . P
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'
O O 0.0106 0.0060 '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
C2 C1 C4 109.90(16) .
C2 C1 C3 108.02(16) .
C4 C1 C3 108.45(16) .
C2 C1 P1 118.11(14) .
C4 C1 P1 107.00(14) .
C3 C1 P1 104.96(13) .
C1 C2 H2A 109.5 .
C1 C2 H2B 109.5 .
H2A C2 H2B 109.5 .
C1 C2 H2C 109.5 .
H2A C2 H2C 109.5 .
H2B C2 H2C 109.5 .
C1 C3 H3A 109.5 .
C1 C3 H3B 109.5 .
H3A C3 H3B 109.5 .
C1 C3 H3C 109.5 .
H3A C3 H3C 109.5 .
H3B C3 H3C 109.5 .
C1 C4 H4A 109.5 .
C1 C4 H4B 109.5 .
H4A C4 H4B 109.5 .
C1 C4 H4C 109.5 .
H4A C4 H4C 109.5 .
H4B C4 H4C 109.5 .
C8 C5 C7 109.39(17) .
C8 C5 C6 107.86(17) .
C7 C5 C6 107.93(17) .
C8 C5 P1 118.35(14) .
C7 C5 P1 106.85(14) .
C6 C5 P1 106.03(14) .
C5 C6 H6A 109.5 .
C5 C6 H6B 109.5 .
H6A C6 H6B 109.5 .
C5 C6 H6C 109.5 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
C5 C7 H7A 109.5 .
C5 C7 H7B 109.5 .
H7A C7 H7B 109.5 .
C5 C7 H7C 109.5 .
H7A C7 H7C 109.5 .
H7B C7 H7C 109.5 .
C5 C8 H8A 109.5 .
C5 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
C5 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
C10 C9 C14 116.64(18) .
C10 C9 P1 114.64(15) .
C14 C9 P1 128.65(15) .
C11 C10 C9 122.2(2) .
C11 C10 H10 118.9 .
C9 C10 H10 118.9 .
C12 C11 C10 119.5(2) .
C12 C11 H11 120.2 .
C10 C11 H11 120.2 .
C13 C12 C11 120.1(2) .
C13 C12 H12 119.9 .
C11 C12 H12 119.9 .
C12 C13 C14 120.1(2) .
C12 C13 H13 120.0 .
C14 C13 H13 120.0 .
O1 C14 C13 122.34(18) .
O1 C14 C9 116.26(18) .
C13 C14 C9 121.39(19) .
O1 C15 H15A 109.5 .
O1 C15 H15B 109.5 .
H15A C15 H15B 109.5 .
O1 C15 H15C 109.5 .
H15A C15 H15C 109.5 .
H15B C15 H15C 109.5 .
C14 O1 C15 117.50(16) .
C9 P1 C1 103.97(9) .
C9 P1 C5 109.23(9) .
C1 P1 C5 110.76(9) .
C9 P1 Pd1 110.75(7) .
C1 P1 Pd1 108.71(6) .
C5 P1 Pd1 113.05(7) .
P1 Pd1 P1 180.0 3_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.530(3) .
C1 C4 1.532(3) .
C1 C3 1.540(3) .
C1 P1 1.888(2) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 C8 1.529(3) .
C5 C7 1.532(3) .
C5 C6 1.541(3) .
C5 P1 1.900(2) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.398(3) .
C9 C14 1.407(3) .
C9 P1 1.849(2) .
C10 C11 1.386(3) .
C10 H10 0.9500 .
C11 C12 1.383(3) .
C11 H11 0.9500 .
C12 C13 1.380(3) .
C12 H12 0.9500 .
C13 C14 1.389(3) .
C13 H13 0.9500 .
C14 O1 1.371(2) .
C15 O1 1.431(2) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
P1 Pd1 2.3021(5) .
Pd1 P1 2.3020(5) 3_666
