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#$Date: 2016-09-07 18:11:00 +0300 (Wed, 07 Sep 2016) $
#$Revision: 186259 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/66/4086644.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_4086644
loop_
_publ_author_name
'Behnia, Ava'
'Boyle, Paul D.'
'Blacquiere, Johanna M.'
'Puddephatt, Richard J.'
_publ_section_title
;
 Selective Oxygen Atom Insertion into an Aryl--Palladium Bond
;
_journal_issue                   16
_journal_name_full               Organometallics
_journal_page_first              2645
_journal_paper_doi               10.1021/acs.organomet.6b00387
_journal_volume                  35
_journal_year                    2016
_chemical_formula_sum            'C20 H24 Br2 N2 Pd'
_chemical_formula_weight         558.63
_space_group_crystal_system      tetragonal
_space_group_IT_number           110
_space_group_name_Hall           'I 4bw -2c'
_space_group_name_H-M_alt        'I 41 c d'
_symmetry_space_group_name_Hall  'I 4bw -2c'
_symmetry_space_group_name_H-M   'I 41 c d'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.252(4)
_cell_length_b                   17.252
_cell_length_c                   14.344(4)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    110
_cell_measurement_theta_max      39.63
_cell_measurement_theta_min      3.00
_cell_volume                     4269.2(15)
_computing_cell_refinement       SAINT
_computing_data_collection       Apex2
_computing_data_reduction        SAINT
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      110
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Bruker Apex2'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa Axis Apex2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            106381
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         42.573
_diffrn_reflns_theta_min         3.295
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    4.618
_exptl_absorpt_correction_T_max  0.7484
_exptl_absorpt_correction_T_min  0.6167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_description       prism
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.180
_refine_diff_density_max         2.952
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.128
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.019(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         7246
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0275P)²+8.7745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0789
_reflns_Friedel_coverage         0.944
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                5107
_reflns_number_total             7246
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om6b00387_si_003.cif
_cod_data_source_block           complex_2a
_cod_depositor_comments
'Adding full bibliography for 4086643--4086646.cif.'
_cod_original_cell_volume        4269(2)
_cod_database_code               4086644
_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   0.395
_shelx_estimated_absorpt_t_max   0.490
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-y, x+1/2, z+1/4'
'y+1/2, -x, z+3/4'
'x, -y, z+1/2'
'-x+1/2, y+1/2, z'
'-y, -x+1/2, z+3/4'
'y+1/2, x, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1, z+1'
'-y+1/2, x+1, z+3/4'
'y+1, -x+1/2, z+5/4'
'x+1/2, -y+1/2, z+1'
'-x+1, y+1, z+1/2'
'-y+1/2, -x+1, z+5/4'
'y+1, x+1/2, z+3/4'
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
Pd1 Pd 0.5000 0.5000 0.46336(2) 0.01203(4) Uani 1 2 d S T P
Br1 Br 0.42702(2) 0.42922(2) 0.34829(2) 0.01988(6) Uani 1 1 d . . .
N1 N 0.55959(13) 0.54605(13) 0.57146(18) 0.0150(4) Uani 1 1 d . . .
C1 C 0.53397(18) 0.52572(19) 0.6521(2) 0.0201(5) Uani 1 1 d . . .
H1 H 0.5576 0.5429 0.7083 0.024 Uiso 1 1 calc R U .
C2 C 0.62788(15) 0.59379(16) 0.5689(2) 0.0148(4) Uani 1 1 d . . .
C3 C 0.61878(17) 0.67456(16) 0.5676(2) 0.0186(5) Uani 1 1 d . . .
C4 C 0.6856(2) 0.71933(19) 0.5688(3) 0.0241(5) Uani 1 1 d . . .
H4 H 0.6811 0.7742 0.5696 0.029 Uiso 1 1 calc R U .
C5 C 0.75952(18) 0.6858(2) 0.5687(3) 0.0239(6) Uani 1 1 d . . .
C6 C 0.76536(17) 0.60485(19) 0.5676(3) 0.0223(5) Uani 1 1 d . . .
H6 H 0.8153 0.5816 0.5670 0.027 Uiso 1 1 calc R U .
C7 C 0.69999(17) 0.55770(17) 0.5672(2) 0.0194(5) Uani 1 1 d . . .
C8 C 0.53889(19) 0.70971(18) 0.5690(4) 0.0287(7) Uani 1 1 d . . .
H8A H 0.5095 0.6885 0.6216 0.043 Uiso 1 1 calc R U .
H8B H 0.5121 0.6974 0.5106 0.043 Uiso 1 1 calc R U .
H8C H 0.5431 0.7661 0.5757 0.043 Uiso 1 1 calc R U .
C9 C 0.8316(2) 0.7351(2) 0.5722(3) 0.0351(8) Uani 1 1 d . . .
H9A H 0.8406 0.7524 0.6363 0.053 Uiso 1 1 calc R U .
H9B H 0.8250 0.7803 0.5316 0.053 Uiso 1 1 calc R U .
H9C H 0.8761 0.7046 0.5508 0.053 Uiso 1 1 calc R U .
C10 C 0.7065(2) 0.47025(19) 0.5649(3) 0.0287(7) Uani 1 1 d . . .
H10A H 0.6835 0.4485 0.6217 0.043 Uiso 1 1 calc R U .
H10B H 0.7612 0.4554 0.5614 0.043 Uiso 1 1 calc R U .
H10C H 0.6789 0.4502 0.5102 0.043 Uiso 1 1 calc R U .
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'
Br Br -0.2901 2.4595 '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'
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
N1 Pd1 N1 79.92(14) . 10_554
N1 Pd1 Br1 171.92(7) . .
N1 Pd1 Br1 93.47(7) 10_554 .
N1 Pd1 Br1 93.47(7) . 10_554
N1 Pd1 Br1 171.92(7) 10_554 10_554
Br1 Pd1 Br1 93.47(3) . 10_554
C1 N1 C2 117.4(3) . .
C1 N1 Pd1 114.1(2) . .
C2 N1 Pd1 128.46(19) . .
N1 C1 C1 115.98(17) . 10_554
N1 C1 H1 122.0 . .
C1 C1 H1 122.0 10_554 .
C7 C2 C3 123.0(3) . .
C7 C2 N1 118.5(2) . .
C3 C2 N1 118.5(2) . .
C4 C3 C2 117.4(3) . .
C4 C3 C8 122.4(3) . .
C2 C3 C8 120.2(3) . .
C3 C4 C5 121.8(3) . .
C3 C4 H4 119.1 . .
C5 C4 H4 119.1 . .
C6 C5 C4 118.5(3) . .
C6 C5 C9 120.2(3) . .
C4 C5 C9 121.2(3) . .
C7 C6 C5 121.7(3) . .
C7 C6 H6 119.2 . .
C5 C6 H6 119.2 . .
C6 C7 C2 117.6(3) . .
C6 C7 C10 121.6(3) . .
C2 C7 C10 120.8(3) . .
C3 C8 H8A 109.5 . .
C3 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C3 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C5 C9 H9A 109.5 . .
C5 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C5 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C7 C10 H10A 109.5 . .
C7 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C7 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 N1 2.023(3) .
Pd1 N1 2.023(3) 10_554
Pd1 Br1 2.4085(5) .
Pd1 Br1 2.4085(5) 10_554
N1 C1 1.287(4) .
N1 C2 1.438(3) .
C1 C1 1.470(6) 10_554
C1 H1 0.9500 .
C2 C7 1.391(4) .
C2 C3 1.402(4) .
C3 C4 1.387(4) .
C3 C8 1.506(4) .
C4 C5 1.400(5) .
C4 H4 0.9500 .
C5 C6 1.400(5) .
C5 C9 1.507(5) .
C6 C7 1.390(4) .
C6 H6 0.9500 .
C7 C10 1.513(4) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C2 N1 C1 C1 -177.5(3) 10_554
Pd1 N1 C1 C1 -0.9(5) 10_554
C1 N1 C2 C7 88.7(3) .
Pd1 N1 C2 C7 -87.3(3) .
C1 N1 C2 C3 -91.8(4) .
Pd1 N1 C2 C3 92.1(3) .
C7 C2 C3 C4 -3.0(5) .
N1 C2 C3 C4 177.6(3) .
C7 C2 C3 C8 179.6(3) .
N1 C2 C3 C8 0.1(5) .
C2 C3 C4 C5 1.7(5) .
C8 C3 C4 C5 179.1(4) .
C3 C4 C5 C6 0.0(6) .
C3 C4 C5 C9 -178.6(4) .
C4 C5 C6 C7 -0.5(6) .
C9 C5 C6 C7 178.1(3) .
C5 C6 C7 C2 -0.7(5) .
C5 C6 C7 C10 179.4(4) .
C3 C2 C7 C6 2.5(5) .
N1 C2 C7 C6 -178.1(3) .
C3 C2 C7 C10 -177.6(3) .
N1 C2 C7 C10 1.9(5) .
