#------------------------------------------------------------------------------
#$Date: 2016-08-05 07:04:52 +0300 (Fri, 05 Aug 2016) $
#$Revision: 185005 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/19/4031990.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_4031990
loop_
_publ_author_name
'Nishikata, Takashi'
'Abela, Alexander R.'
'Huang, Shenlin'
'Lipshutz, Bruce H.'
_publ_section_title
;
 Cationic Pd(II)-catalyzed C-H activation/cross-coupling reactions at room
 temperature: synthetic and mechanistic studies.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1040
_journal_page_last               1064
_journal_paper_doi               10.3762/bjoc.12.99
_journal_volume                  12
_journal_year                    2016
_chemical_formula_sum            'C14 H19 B F4 N4 O2 Pd'
_chemical_formula_weight         468.54
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.328(5)
_cell_length_b                   6.6951(13)
_cell_length_c                   10.795(2)
_cell_measurement_temperature    150(2)
_cell_volume                     1830.5(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scan'
_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  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11933
_diffrn_reflns_theta_full        26.76
_diffrn_reflns_theta_max         26.76
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    1.068
_exptl_absorpt_correction_T_max  0.291
_exptl_absorpt_correction_T_min  0.215
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.154
_refine_ls_extinction_coef       0.0040(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.345
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2076
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.342
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0516P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                1847
_reflns_number_total             2076
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-12-99-S2.cif
_cod_data_source_block           l
_cod_depositor_comments          'Adding full bibliography for 4031990.cif.'
_cod_original_cell_volume        1830.6(6)
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4031990
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
B B 0.7970(3) 0.7500 0.5625(6) 0.0487(16) Uani 1 2 d S
C1 C 1.1670(2) 0.2500 -0.1426(5) 0.0400(13) Uani 1 2 d S
C2 C 1.10798(17) 0.2500 0.0302(4) 0.0250(9) Uani 1 2 d S
C3 C 1.06304(15) 0.2500 -0.0420(5) 0.0259(10) Uani 1 2 d S
H3 H 1.0657 0.2500 -0.1279 0.031 Uiso 1 2 calc SR
C4 C 1.01423(17) 0.2500 0.0141(4) 0.0278(10) Uani 1 2 d S
H4 H 0.9844 0.2500 -0.0363 0.033 Uiso 1 2 calc SR
C5 C 1.00701(15) 0.2500 0.1414(4) 0.0195(8) Uani 1 2 d S
C6 C 1.05302(18) 0.2500 0.2130(4) 0.0228(9) Uani 1 2 d S
C7 C 1.10267(16) 0.2500 0.1582(4) 0.0226(9) Uani 1 2 d S
H7 H 1.1327 0.2500 0.2078 0.027 Uiso 1 2 calc SR
C8 C 1.01369(17) 0.2500 0.4234(4) 0.0251(9) Uani 1 2 d S
C9 C 1.0772(2) 0.2500 0.5942(5) 0.0469(15) Uani 1 2 d SD
C10 C 0.9815(2) 0.2500 0.6360(5) 0.0341(11) Uani 1 2 d SD
C11 C 0.87021(17) 0.2500 -0.0273(5) 0.0279(10) Uani 1 2 d S
C12 C 0.83642(19) 0.2500 -0.1359(5) 0.0349(11) Uani 1 2 d SD
C13 C 0.82026(19) 0.2500 0.3480(4) 0.0325(10) Uani 1 2 d S
C14 C 0.76825(19) 0.2500 0.4028(6) 0.0405(13) Uani 1 2 d SD
F1 F 0.79500(13) 0.7500 0.4347(3) 0.0542(9) Uani 1 2 d S
F2 F 0.82573(15) 0.9112(4) 0.6026(3) 0.0958(12) Uani 1 1 d .
F3 F 0.74933(17) 0.8216(9) 0.6066(4) 0.073(2) Uani 0.50 1 d P
H1A H 1.204(3) 0.2500 -0.146(6) 0.061(19) Uiso 1 2 d S
H9A H 1.069(2) 0.2500 0.6814(18) 0.12(4) Uiso 1 2 d SD
H10A H 0.9479(11) 0.2500 0.595(4) 0.053(18) Uiso 1 2 d SD
H12A H 0.8000(7) 0.2500 -0.114(4) 0.052(17) Uiso 1 2 d SD
H14A H 0.741(2) 0.2500 0.341(5) 0.09(3) Uiso 1 2 d SD
H1B H 1.1525(14) 0.131(5) -0.179(4) 0.038(10) Uiso 1 1 d .
H9B H 1.0986(14) 0.135(4) 0.578(3) 0.065(14) Uiso 1 1 d D
H10B H 0.9836(11) 0.131(3) 0.686(3) 0.031(9) Uiso 1 1 d D
H12B H 0.8436(13) 0.142(5) -0.191(3) 0.073(16) Uiso 1 1 d D
H14B H 0.7640(19) 0.135(5) 0.454(4) 0.12(2) Uiso 1 1 d D
N1 N 1.05423(14) 0.2500 0.3448(4) 0.0237(8) Uani 1 2 d S
H1 H 1.0851 0.2500 0.3779 0.028 Uiso 1 2 calc SR
N2 N 1.02393(15) 0.2500 0.5451(4) 0.0309(9) Uani 1 2 d S
N3 N 0.89804(14) 0.2500 0.0556(4) 0.0289(9) Uani 1 2 d S
N4 N 0.86080(16) 0.2500 0.3057(4) 0.0304(9) Uani 1 2 d S
O1 O 1.15893(13) 0.2500 -0.0112(3) 0.0375(9) Uani 1 2 d S
O2 O 0.96607(12) 0.2500 0.3877(3) 0.0290(7) Uani 1 2 d S
Pd Pd 0.935908(12) 0.2500 0.21770(3) 0.02396(17) Uani 1 2 d S
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'
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
F2 B F2 103.8(5) . 7_575
F2 B F1 109.6(4) . .
F2 B F1 109.6(4) 7_575 .
F2 B F3 128.8(5) . 7_575
F2 B F3 94.7(4) 7_575 7_575
F1 B F3 108.1(5) . 7_575
F2 B F3 94.7(4) . .
F2 B F3 128.8(5) 7_575 .
F1 B F3 108.1(5) . .
F3 B F3 40.6(5) 7_575 .
O1 C1 H1A 100(4) . .
O1 C1 H1B 110(2) . .
H1A C1 H1B 112(3) . .
O1 C2 C3 126.5(4) . .
O1 C2 C7 114.7(4) . .
C3 C2 C7 118.9(4) . .
C4 C3 C2 119.5(5) . .
C4 C3 H3 120.3 . .
C2 C3 H3 120.3 . .
C3 C4 C5 123.7(4) . .
C3 C4 H4 118.2 . .
C5 C4 H4 118.2 . .
C4 C5 C6 116.0(4) . .
C4 C5 Pd 122.1(3) . .
C6 C5 Pd 121.9(3) . .
C7 C6 C5 121.2(4) . .
C7 C6 N1 114.0(4) . .
C5 C6 N1 124.8(4) . .
C2 C7 C6 120.8(4) . .
C2 C7 H7 119.6 . .
C6 C7 H7 119.6 . .
O2 C8 N1 122.7(4) . .
O2 C8 N2 118.9(4) . .
N1 C8 N2 118.4(4) . .
N2 C9 H9A 100(4) . .
N2 C9 H9B 117(3) . .
H9A C9 H9B 107.2(15) . .
N2 C10 H10A 110(3) . .
N2 C10 H10B 109.6(19) . .
H10A C10 H10B 107.9(14) . .
N3 C11 C12 177.9(5) . .
C11 C12 H12A 112(3) . .
C11 C12 H12B 113(3) . .
H12A C12 H12B 109.7(15) . .
N4 C13 C14 179.7(5) . .
C13 C14 H14A 111(4) . .
C13 C14 H14B 110(3) . .
H14A C14 H14B 108.9(15) . .
F3 F3 B 69.7(3) 7_575 .
C8 N1 C6 128.3(4) . .
C8 N1 H1 115.8 . .
C6 N1 H1 115.8 . .
C8 N2 C9 122.6(4) . .
C8 N2 C10 121.2(4) . .
C9 N2 C10 116.2(4) . .
C11 N3 Pd 170.5(4) . .
C13 N4 Pd 177.4(4) . .
C2 O1 C1 117.4(4) . .
C8 O2 Pd 130.3(3) . .
C5 Pd O2 91.97(15) . .
C5 Pd N3 94.16(16) . .
O2 Pd N3 173.87(14) . .
C5 Pd N4 178.02(16) . .
O2 Pd N4 86.05(14) . .
N3 Pd N4 87.82(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B F2 1.372(5) .
B F2 1.372(5) 7_575
B F1 1.381(7) .
B F3 1.384(8) 7_575
B F3 1.384(8) .
C1 O1 1.433(6) .
C1 H1A 0.93(6) .
C1 H1B 0.96(4) .
C2 O1 1.366(5) .
C2 C3 1.380(6) .
C2 C7 1.388(6) .
C3 C4 1.377(6) .
C3 H3 0.9300 .
C4 C5 1.387(6) .
C4 H4 0.9300 .
C5 C6 1.399(6) .
C5 Pd 1.980(4) .
C6 C7 1.390(6) .
C6 N1 1.422(6) .
C7 H7 0.9300 .
C8 O2 1.266(5) .
C8 N1 1.332(6) .
C8 N2 1.340(6) .
C9 N2 1.449(7) .
C9 H9A 0.961(10) .
C9 H9B 0.961(10) .
C10 N2 1.455(6) .
C10 H10A 0.958(10) .
C10 H10B 0.961(10) .
C11 N3 1.139(6) .
C11 C12 1.451(7) .
C12 H12A 0.951(10) .
C12 H12B 0.952(10) .
C13 N4 1.123(6) .
C13 C14 1.444(7) .
C14 H14A 0.956(10) .
C14 H14B 0.953(10) .
F3 F3 0.959(12) 7_575
N1 H1 0.8600 .
N3 Pd 1.995(4) .
N4 Pd 2.127(4) .
O2 Pd 1.987(3) .
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_1
_geom_torsion_site_symmetry_4
O1 C2 C3 C4 180.0 . .
C7 C2 C3 C4 0.0 . .
C2 C3 C4 C5 0.0 . .
C3 C4 C5 C6 0.0 . .
C3 C4 C5 Pd 180.0 . .
C4 C5 C6 C7 0.0 . .
Pd C5 C6 C7 180.0 . .
C4 C5 C6 N1 180.0 . .
Pd C5 C6 N1 0.0 . .
O1 C2 C7 C6 180.0 . .
C3 C2 C7 C6 0.0 . .
C5 C6 C7 C2 0.0 . .
N1 C6 C7 C2 180.0 . .
F2 B F3 F3 -150.7(4) . 7_575
F2 B F3 F3 -38.8(4) 7_575 7_575
F1 B F3 F3 97.0(2) . 7_575
O2 C8 N1 C6 0.0 . .
N2 C8 N1 C6 180.0 . .
C7 C6 N1 C8 180.0 . .
C5 C6 N1 C8 0.0 . .
O2 C8 N2 C9 180.0 . .
N1 C8 N2 C9 0.0 . .
O2 C8 N2 C10 0.0 . .
N1 C8 N2 C10 180.0 . .
C12 C11 N3 Pd 180.000(3) . .
C14 C13 N4 Pd 180.0(3) . .
C3 C2 O1 C1 0.0 . .
C7 C2 O1 C1 180.0 . .
N1 C8 O2 Pd 0.0 . .
N2 C8 O2 Pd 180.0 . .
C4 C5 Pd O2 180.0 . .
C6 C5 Pd O2 0.0 . .
C4 C5 Pd N3 0.0 . .
C6 C5 Pd N3 180.0 . .
C4 C5 Pd N4 180.000(4) . .
C6 C5 Pd N4 0.000(4) . .
C8 O2 Pd C5 0.0 . .
C8 O2 Pd N3 180.0 . .
C8 O2 Pd N4 180.0 . .
C11 N3 Pd C5 180.0 . .
C11 N3 Pd O2 0.000(1) . .
C11 N3 Pd N4 0.0 . .
C13 N4 Pd C5 180.000(7) . .
C13 N4 Pd O2 180.000(6) . .
C13 N4 Pd N3 0.000(6) . .
