#------------------------------------------------------------------------------
#$Date: 2016-03-22 14:06:56 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178985 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/08/4120828.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_4120828
loop_
_publ_author_name
'Anthony R. Mazzotti'
'Michael G. Campbell'
'Pingping Tang'
'Jennifer M. Murphy'
'Tobias Ritter'
_publ_section_title
;
 Palladium(III)-Catalyzed Fluorination of Arylboronic Acid Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14012
_journal_page_last               14015
_journal_paper_doi               10.1021/ja405919z
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C34 H32 B2 F8 N6 O Pd'
_chemical_formula_weight         820.68
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.0800(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1099(7)
_cell_length_b                   12.6815(8)
_cell_length_c                   20.7558(13)
_cell_measurement_reflns_used    20225
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      27.152
_cell_measurement_theta_min      2.325
_cell_volume                     3187.5(3)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2009.3.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2009)'
_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      100(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            49913
_diffrn_reflns_theta_full        27.20
_diffrn_reflns_theta_max         27.20
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  0.8090
_exptl_absorpt_correction_T_min  0.7346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_description       block
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         7077
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0244
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0297P)²+1.9445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0602
_reflns_number_gt                6487
_reflns_number_total             7077
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja405919z_si_004.cif
_cod_data_source_block           mgc
_cod_database_code               4120828
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C3 C 0.8451(2) 0.9074(2) 0.39922(12) 0.0353(6) Uani 1 1 d . . .
H3 H 0.8529 0.8395 0.3805 0.042 Uiso 1 1 calc R . .
C2 C 0.8194(2) 0.9942(2) 0.36143(12) 0.0345(6) Uani 1 1 d . . .
H2 H 0.8072 0.9868 0.3164 0.041 Uiso 1 1 calc R . .
C1 C 0.8121(2) 1.0915(2) 0.39084(13) 0.0335(6) Uani 1 1 d . . .
H1 H 0.7992 1.1512 0.3642 0.040 Uiso 1 1 calc R . .
N1 N 0.82198(17) 1.10758(17) 0.45450(10) 0.0302(5) Uani 1 1 d . . .
C5 C 0.84425(19) 1.02211(19) 0.49109(11) 0.0253(5) Uani 1 1 d . . .
C6 C 0.85326(19) 1.04112(18) 0.56184(11) 0.0236(5) Uani 1 1 d . . .
C7 C 0.8324(2) 1.1403(2) 0.58806(13) 0.0337(6) Uani 1 1 d . . .
H7 H 0.8122 1.1976 0.5611 0.040 Uiso 1 1 calc R . .
C8 C 0.8416(3) 1.1540(2) 0.65420(14) 0.0372(6) Uani 1 1 d . . .
H8 H 0.8257 1.2205 0.6731 0.045 Uiso 1 1 calc R . .
C9 C 0.8742(2) 1.0701(2) 0.69236(12) 0.0310(5) Uani 1 1 d . . .
H9 H 0.8829 1.0780 0.7376 0.037 Uiso 1 1 calc R . .
C10 C 0.89403(18) 0.97344(18) 0.66234(11) 0.0217(4) Uani 1 1 d . . .
C11 C 0.93300(18) 0.88221(18) 0.70074(10) 0.0191(4) Uani 1 1 d . . .
C12 C 1.01054(19) 0.8954(2) 0.74974(11) 0.0252(5) Uani 1 1 d . . .
H12 H 1.0352 0.9641 0.7610 0.030 Uiso 1 1 calc R . .
C13 C 1.0514(2) 0.8085(2) 0.78185(11) 0.0294(5) Uani 1 1 d . . .
H13 H 1.1058 0.8166 0.8145 0.035 Uiso 1 1 calc R . .
C14 C 1.0123(2) 0.7097(2) 0.76592(12) 0.0287(5) Uani 1 1 d . . .
H14 H 1.0397 0.6487 0.7872 0.034 Uiso 1 1 calc R . .
C15 C 0.93321(19) 0.70099(19) 0.71872(11) 0.0232(5) Uani 1 1 d . . .
H15 H 0.9049 0.6331 0.7087 0.028 Uiso 1 1 calc R . .
C16 C 0.63141(18) 0.85459(19) 0.71558(10) 0.0220(5) Uani 1 1 d . . .
H16 H 0.6964 0.8767 0.7374 0.026 Uiso 1 1 calc R . .
C17 C 0.52873(19) 0.8791(2) 0.74175(11) 0.0269(5) Uani 1 1 d . . .
H17 H 0.5239 0.9186 0.7805 0.032 Uiso 1 1 calc R . .
C18 C 0.4341(2) 0.8456(2) 0.71096(12) 0.0334(6) Uani 1 1 d . . .
H18 H 0.3636 0.8601 0.7289 0.040 Uiso 1 1 calc R . .
C19 C 0.4432(2) 0.7902(2) 0.65306(12) 0.0291(5) Uani 1 1 d . . .
H19 H 0.3790 0.7668 0.6310 0.035 Uiso 1 1 calc R . .
C20 C 0.54694(19) 0.76970(19) 0.62829(11) 0.0214(5) Uani 1 1 d . . .
C21 C 0.56618(18) 0.71457(18) 0.56668(11) 0.0205(4) Uani 1 1 d . . .
C22 C 0.4875(2) 0.6732(2) 0.52486(11) 0.0262(5) Uani 1 1 d . . .
H22 H 0.4109 0.6794 0.5339 0.031 Uiso 1 1 calc R . .
C23 C 0.5242(2) 0.6223(2) 0.46939(12) 0.0279(5) Uani 1 1 d . . .
H23 H 0.4717 0.5940 0.4400 0.034 Uiso 1 1 calc R . .
C24 C 0.6357(2) 0.61221(19) 0.45632(11) 0.0255(5) Uani 1 1 d . . .
H24 H 0.6602 0.5769 0.4186 0.031 Uiso 1 1 calc R . .
C25 C 0.71123(19) 0.65486(17) 0.49968(10) 0.0195(4) Uani 1 1 d . . .
C26 C 0.83270(19) 0.64901(17) 0.49690(10) 0.0192(4) Uani 1 1 d . . .
C27 C 0.89134(19) 0.60934(18) 0.44520(11) 0.0220(5) Uani 1 1 d . . .
H27 H 0.8538 0.5840 0.4081 0.026 Uiso 1 1 calc R . .
C28 C 1.0058(2) 0.60692(18) 0.44818(11) 0.0236(5) Uani 1 1 d . . .
H28 H 1.0472 0.5797 0.4131 0.028 Uiso 1 1 calc R . .
C29 C 1.05934(19) 0.64433(17) 0.50251(11) 0.0222(5) Uani 1 1 d . . .
H29 H 1.1376 0.6427 0.5054 0.027 Uiso 1 1 calc R . .
C30 C 0.99614(18) 0.68430(17) 0.55281(11) 0.0198(4) Uani 1 1 d . . .
H30 H 1.0326 0.7106 0.5900 0.024 Uiso 1 1 calc R . .
C4 C 0.85909(19) 0.92196(19) 0.46529(11) 0.0241(3) Uani 1 1 d . . .
H4 H 0.8785 0.8643 0.4923 0.029 Uiso 1 1 calc R . .
N2 N 0.88255(17) 0.95781(15) 0.59877(9) 0.0241(3) Uani 1 1 d . . .
N3 N 0.89418(15) 0.78506(15) 0.68607(8) 0.0178(4) Uani 1 1 d . . .
N4 N 0.64069(15) 0.80057(15) 0.66041(9) 0.0191(4) Uani 1 1 d . . .
N5 N 0.67392(15) 0.70523(14) 0.55228(9) 0.0185(4) Uani 1 1 d . . .
N6 N 0.88606(15) 0.68698(14) 0.55052(9) 0.0173(4) Uani 1 1 d . . .
Pd71 Pd 0.780900(14) 0.752472(12) 0.615461(8) 0.01519(4) Uani 1 1 d . . .
B2 B 0.7724(2) 0.4190(2) 0.32478(12) 0.0262(4) Uani 1 1 d . . .
F5 F 0.74755(14) 0.35101(14) 0.27471(8) 0.0477(4) Uani 1 1 d . B .
B1 B 0.2843(2) 0.5437(2) 0.36715(12) 0.0262(4) Uani 1 1 d . . .
F1 F 0.18716(12) 0.50295(12) 0.34059(7) 0.0340(3) Uani 1 1 d . . .
F2 F 0.37174(12) 0.47490(11) 0.35575(7) 0.0297(3) Uani 1 1 d . . .
F3 F 0.27044(12) 0.55588(12) 0.43319(6) 0.0335(3) Uani 1 1 d . . .
F4 F 0.30596(12) 0.64052(11) 0.33900(7) 0.0324(3) Uani 1 1 d . . .
C1S C 0.4315(7) 0.9130(10) 0.4264(4) 0.054(2) Uani 0.50 1 d PD A -1
H1SA H 0.4250 0.8811 0.3835 0.080 Uiso 0.50 1 calc PR A -1
H1SB H 0.4012 0.9846 0.4253 0.080 Uiso 0.50 1 calc PR A -1
H1SC H 0.3905 0.8705 0.4577 0.080 Uiso 0.50 1 calc PR A -1
C2S C 0.5501(5) 0.9173(5) 0.4455(3) 0.0389(13) Uani 0.50 1 d PD A -1
H2SA H 0.5850 0.8481 0.4369 0.047 Uiso 0.50 1 calc PR A -1
H2SB H 0.5886 0.9709 0.4190 0.047 Uiso 0.50 1 calc PR A -1
O1S O 0.5627(3) 0.9433(3) 0.51300(18) 0.0387(9) Uani 0.50 1 d PD A -1
C3S C 0.5443(6) 1.0515(4) 0.5246(3) 0.0427(14) Uani 0.50 1 d PD A -1
H3SA H 0.4729 1.0734 0.5057 0.051 Uiso 0.50 1 calc PR A -1
H3SB H 0.6037 1.0940 0.5046 0.051 Uiso 0.50 1 calc PR A -1
C4S C 0.5432(11) 1.0689(9) 0.5959(4) 0.066(3) Uani 0.50 1 d PD A -1
H4SA H 0.5362 1.1445 0.6049 0.099 Uiso 0.50 1 calc PR A -1
H4SB H 0.6121 1.0424 0.6147 0.099 Uiso 0.50 1 calc PR A -1
H4SC H 0.4805 1.0312 0.6149 0.099 Uiso 0.50 1 calc PR A -1
F6 F 0.88909(17) 0.44680(16) 0.32573(10) 0.0366(5) Uani 0.763(2) 1 d PD B 1
F7 F 0.7511(2) 0.3790(2) 0.38625(11) 0.0434(6) Uani 0.763(2) 1 d PD B 1
F8 F 0.7201(2) 0.51513(19) 0.31673(11) 0.0527(6) Uani 0.763(2) 1 d PD B 1
F6B F 0.8223(6) 0.4911(5) 0.3068(3) 0.0366(5) Uani 0.237(2) 1 d PD B 2
F7B F 0.7921(7) 0.3442(7) 0.3649(3) 0.0434(6) Uani 0.237(2) 1 d PD B 2
F8B F 0.6491(7) 0.4513(6) 0.3403(4) 0.0527(6) Uani 0.237(2) 1 d PD B 2
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'
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'
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C3 C4 118.6(3)
C1 C2 C3 118.3(2)
N1 C1 C2 124.4(2)
C1 N1 C5 116.7(2)
N1 C5 C4 122.9(2)
N1 C5 C6 116.0(2)
C4 C5 C6 121.2(2)
N2 C6 C7 122.1(2)
N2 C6 C5 116.8(2)
C7 C6 C5 121.1(2)
C8 C7 C6 119.0(2)
C9 C8 C7 119.4(2)
C8 C9 C10 118.0(2)
N2 C10 C9 123.5(2)
N2 C10 C11 116.50(19)
C9 C10 C11 120.0(2)
N3 C11 C12 120.5(2)
N3 C11 C10 118.66(19)
C12 C11 C10 120.9(2)
C13 C12 C11 119.9(2)
C12 C13 C14 119.1(2)
C15 C14 C13 118.9(2)
N3 C15 C14 122.6(2)
N4 C16 C17 121.6(2)
C18 C17 C16 119.5(2)
C17 C18 C19 119.2(2)
C20 C19 C18 119.2(2)
N4 C20 C19 121.1(2)
N4 C20 C21 115.1(2)
C19 C20 C21 123.8(2)
N5 C21 C22 119.5(2)
N5 C21 C20 112.88(19)
C22 C21 C20 127.6(2)
C21 C22 C23 118.2(2)
C24 C23 C22 121.2(2)
C23 C24 C25 118.5(2)
N5 C25 C24 119.3(2)
N5 C25 C26 113.11(19)
C24 C25 C26 127.6(2)
N6 C26 C27 121.0(2)
N6 C26 C25 114.8(2)
C27 C26 C25 124.2(2)
C26 C27 C28 119.2(2)
C29 C28 C27 119.7(2)
C28 C29 C30 118.6(2)
N6 C30 C29 122.2(2)
C5 C4 C3 119.0(2)
C10 N2 C6 118.0(2)
C15 N3 C11 119.03(19)
C15 N3 Pd71 115.72(16)
C11 N3 Pd71 125.23(15)
C16 N4 C20 119.38(19)
C16 N4 Pd71 128.12(15)
C20 N4 Pd71 112.49(15)
C25 N5 C21 123.38(19)
C25 N5 Pd71 118.15(15)
C21 N5 Pd71 118.07(15)
C30 N6 C26 119.26(19)
C30 N6 Pd71 127.85(15)
C26 N6 Pd71 112.71(14)
N5 Pd71 N4 81.10(8)
N5 Pd71 N6 81.01(7)
N4 Pd71 N6 162.09(7)
N5 Pd71 N3 173.46(8)
N4 Pd71 N3 99.80(7)
N6 Pd71 N3 97.89(7)
F6B B2 F7B 134.0(6)
F6B B2 F5 111.3(4)
F7B B2 F5 93.8(4)
F6B B2 F8 60.3(4)
F7B B2 F8 144.4(5)
F5 B2 F8 111.1(2)
F6B B2 F7 132.6(4)
F7B B2 F7 34.4(4)
F5 B2 F7 114.8(2)
F8 B2 F7 110.2(2)
F6B B2 F6 46.0(4)
F7B B2 F6 89.5(4)
F5 B2 F6 111.8(2)
F8 B2 F6 103.4(2)
F7 B2 F6 104.8(2)
F6B B2 F8B 110.8(5)
F7B B2 F8B 103.5(5)
F5 B2 F8B 96.4(3)
F8 B2 F8B 50.5(3)
F7 B2 F8B 74.5(3)
F6 B2 F8B 148.2(4)
F4 B1 F3 109.9(2)
F4 B1 F2 109.9(2)
F3 B1 F2 109.3(2)
F4 B1 F1 108.7(2)
F3 B1 F1 109.1(2)
F2 B1 F1 110.0(2)
O1S C2S C1S 111.4(5)
C3S O1S C2S 111.8(4)
O1S C3S C4S 108.3(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C3 C2 1.386(4)
C3 C4 1.394(3)
C2 C1 1.380(4)
C1 N1 1.342(3)
N1 C5 1.351(3)
C5 C4 1.390(3)
C5 C6 1.492(3)
C6 N2 1.352(3)
C6 C7 1.393(3)
C7 C8 1.388(4)
C8 C9 1.384(4)
C9 C10 1.396(3)
C10 N2 1.341(3)
C10 C11 1.482(3)
C11 N3 1.353(3)
C11 C12 1.393(3)
C12 C13 1.379(4)
C13 C14 1.380(4)
C14 C15 1.374(3)
C15 N3 1.349(3)
C16 N4 1.339(3)
C16 C17 1.393(3)
C17 C18 1.378(3)
C18 C19 1.397(4)
C19 C20 1.382(3)
C20 N4 1.373(3)
C20 C21 1.476(3)
C21 N5 1.344(3)
C21 C22 1.391(3)
C22 C23 1.393(3)
C23 C24 1.384(4)
C24 C25 1.392(3)
C25 N5 1.344(3)
C25 C26 1.474(3)
C26 N6 1.373(3)
C26 C27 1.382(3)
C27 C28 1.388(3)
C28 C29 1.384(3)
C29 C30 1.391(3)
C30 N6 1.334(3)
N3 Pd71 2.0481(17)
N4 Pd71 2.0321(18)
N5 Pd71 1.9371(17)
N6 Pd71 2.0330(18)
B2 F6B 1.159(7)
B2 F7B 1.283(8)
B2 F5 1.383(3)
B2 F8 1.384(3)
B2 F7 1.397(3)
B2 F6 1.457(4)
B2 F8B 1.581(9)
B1 F4 1.385(3)
B1 F3 1.390(3)
B1 F2 1.392(3)
B1 F1 1.398(3)
C1S C2S 1.490(9)
C2S O1S 1.448(6)
O1S C3S 1.411(6)
C3S C4S 1.497(9)
