#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/33/4103384.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_4103384
loop_
_publ_author_name
'Alison N. Campbell'
'Paul B. White'
'Ilia A. Guzei'
'Shannon S. Stahl'
_publ_contact_author_address
;
Department of Chemistry
University of Wisconsin-Madison
1101 University Ave
Madison, WI  53706
USA
;
_publ_contact_author_email       iguzei@chem.wisc.edu
_publ_contact_author_fax         608-262-0381
_publ_contact_author_name
;
Guzei, Ilia A. 
;
_publ_contact_author_phone       608-263-4694
_publ_section_title
;
 Allylic C-H Acetoxylation with a 4,5-Diazafluorenone-Ligated Palladium
 Catalyst: A Ligand-Based Strategy To Achieve Aerobic Catalytic Turnover
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15116
_journal_page_last               15119
_journal_paper_doi               10.1021/ja105829t
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C14 H11 N2 O Pd, B F4'
_chemical_formula_sum            'C14 H11 B F4 N2 O Pd'
_chemical_formula_weight         416.46
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_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
;
manual editing of the CIF file 
created by SHELXTL Ver. 6.10
and processed with modiCIfer-03272007. 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7592(4)
_cell_length_b                   6.5942(2)
_cell_length_c                   15.8076(5)
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      33.23
_cell_measurement_theta_min      2.96
_cell_volume                     1434.24(8)
_computing_cell_refinement       'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 Ver. 2.1-4 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT Ver. 7.24A'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXTL, OLEX2 (Dolomanov et al., 2009)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.60° ω and 0.6° φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0108
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            40165
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         33.23
_diffrn_reflns_theta_min         2.96
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    1.342
_exptl_absorpt_correction_T_max  0.7846
_exptl_absorpt_correction_T_min  0.7133
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2007)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.929
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      0.891
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0191
_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)+(0.0289P)²+1.3106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0481
_refine_ls_wR_factor_ref         0.0493
_reflns_number_gt                2772
_reflns_number_total             2920
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja105829t_si_003.cif
_cod_data_source_block           stahl86
_cod_original_sg_symbol_Hall     '-P 2ac 2n   '
_cod_original_sg_symbol_H-M      'P n m a '
_cod_database_code               4103384
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.704205(8) 0.2500 0.516001(7) 0.01931(4) Uani 1 2 d S . .
O1 O 0.29140(8) 0.2500 0.36118(9) 0.0246(2) Uani 1 2 d S . .
N1 N 0.63621(9) 0.2500 0.39184(8) 0.0165(2) Uani 1 2 d S . .
N2 N 0.55396(10) 0.2500 0.55797(8) 0.0179(2) Uani 1 2 d S . .
C1 C 0.78489(14) 0.2500 0.62968(13) 0.0298(4) Uani 1 2 d SD . .
H1A H 0.796(3) 0.3932(14) 0.640(3) 0.036 Uiso 0.50 1 d PD A -1
H1B H 0.759(3) 0.158(4) 0.6720(17) 0.036 Uiso 0.50 1 d PD B -1
C2 C 0.84054(16) 0.1448(4) 0.56588(16) 0.0261(4) Uani 0.50 1 d P . -1
H2 H 0.8554 -0.0031 0.5709 0.031 Uiso 0.50 1 calc PR . -1
C3 C 0.85614(13) 0.2500 0.49093(13) 0.0283(3) Uani 1 2 d SD . .
H3A H 0.865(3) 0.3947(11) 0.498(2) 0.034 Uiso 0.50 1 d PD C -1
H3B H 0.882(2) 0.173(5) 0.4437(14) 0.034 Uiso 0.50 1 d PD D -1
C4 C 0.66293(11) 0.2500 0.30937(10) 0.0194(3) Uani 1 2 d S . .
H4 H 0.7302 0.2500 0.2957 0.023 Uiso 1 2 calc SR . .
C5 C 0.59512(11) 0.2500 0.24405(10) 0.0205(3) Uani 1 2 d S . .
H5 H 0.6174 0.2500 0.1872 0.025 Uiso 1 2 calc SR . .
C6 C 0.49506(11) 0.2500 0.25976(10) 0.0195(3) Uani 1 2 d S . .
H6 H 0.4486 0.2500 0.2153 0.023 Uiso 1 2 calc SR . .
C7 C 0.46777(10) 0.2500 0.34415(9) 0.0162(2) Uani 1 2 d S . .
C8 C 0.54080(10) 0.2500 0.40448(9) 0.0147(2) Uani 1 2 d S . .
C9 C 0.49913(11) 0.2500 0.48873(9) 0.0161(2) Uani 1 2 d S . .
C10 C 0.39861(11) 0.2500 0.48418(9) 0.0172(2) Uani 1 2 d S . .
C11 C 0.34688(12) 0.2500 0.55931(11) 0.0220(3) Uani 1 2 d S . .
H11 H 0.2778 0.2500 0.5603 0.026 Uiso 1 2 calc SR . .
C12 C 0.40215(13) 0.2500 0.63375(10) 0.0231(3) Uani 1 2 d S . .
H12 H 0.3699 0.2500 0.6869 0.028 Uiso 1 2 calc SR . .
C13 C 0.50337(13) 0.2500 0.63155(10) 0.0217(3) Uani 1 2 d S . .
H13 H 0.5382 0.2500 0.6835 0.026 Uiso 1 2 calc SR . .
C14 C 0.37198(11) 0.2500 0.39109(10) 0.0177(2) Uani 1 2 d S . .
F1 F 0.1441(3) 0.0761(6) 0.6890(3) 0.0413(8) Uani 0.50 1 d PD E -1
F2 F 0.11296(10) 0.2316(11) 0.56312(7) 0.0255(8) Uani 0.50 1 d PD E -1
F3 F 0.01366(10) 0.2953(4) 0.67624(9) 0.0439(10) Uani 0.50 1 d PD E -1
F4 F 0.1663(2) 0.4153(6) 0.6757(3) 0.0321(6) Uani 0.50 1 d PD E -1
B1 B 0.10841(11) 0.2500 0.65083(9) 0.0269(4) Uani 1 2 d SD . .
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
_geom_angle_publ_flag
C1 Pd1 C3 69.03(8) . . yes
C1 Pd1 C2 39.59(9) . 7_565 yes
C3 Pd1 C2 37.91(8) . 7_565 yes
C1 Pd1 C2 39.59(8) . . yes
C3 Pd1 C2 37.91(8) . . yes
C2 Pd1 C2 37.65(14) 7_565 . yes
C1 Pd1 N2 103.91(7) . . yes
C3 Pd1 N2 172.94(6) . . yes
C2 Pd1 N2 135.95(8) 7_565 . yes
C2 Pd1 N2 135.95(8) . . yes
C1 Pd1 N1 173.78(7) . . yes
C3 Pd1 N1 104.75(6) . . yes
C2 Pd1 N1 134.95(8) 7_565 . yes
C2 Pd1 N1 134.95(8) . . yes
N2 Pd1 N1 82.31(5) . . yes
C8 N1 C4 114.40(13) . . ?
C8 N1 Pd1 106.84(10) . . ?
C4 N1 Pd1 138.76(10) . . ?
C9 N2 C13 114.53(14) . . ?
C9 N2 Pd1 106.78(10) . . ?
C13 N2 Pd1 138.69(11) . . ?
C2 C1 C2 57.4(2) . 7_565 ?
C2 C1 Pd1 71.61(11) . . ?
C2 C1 Pd1 71.61(11) 7_565 . ?
C2 C1 H1A 120(2) . . ?
C2 C1 H1A 64(2) 7_565 . ?
Pd1 C1 H1A 103(2) . . ?
C2 C1 H1B 112(2) . . ?
C2 C1 H1B 167(2) 7_565 . ?
Pd1 C1 H1B 113(2) . . ?
H1A C1 H1B 123(4) . . ?
C3 C2 C1 116.0(2) . . ?
C3 C2 Pd1 70.18(12) . . ?
C1 C2 Pd1 68.80(11) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
Pd1 C2 H2 121.5 . . ?
C2 C3 C2 59.9(2) 7_565 . ?
C2 C3 Pd1 71.91(12) 7_565 . ?
C2 C3 Pd1 71.91(12) . . ?
C2 C3 H3A 55(2) 7_565 . ?
C2 C3 H3A 114(2) . . ?
Pd1 C3 H3A 96(2) . . ?
C2 C3 H3B 167(2) 7_565 . ?
C2 C3 H3B 117(2) . . ?
Pd1 C3 H3B 120(2) . . ?
H3A C3 H3B 124(4) . . ?
N1 C4 C5 122.15(14) . . ?
N1 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C6 121.87(14) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 115.95(14) . . ?
C7 C6 H6 122.0 . . ?
C5 C6 H6 122.0 . . ?
C8 C7 C6 117.78(13) . . ?
C8 C7 C14 107.12(12) . . ?
C6 C7 C14 135.10(13) . . ?
N1 C8 C7 127.85(14) . . ?
N1 C8 C9 121.95(13) . . ?
C7 C8 C9 110.21(13) . . ?
N2 C9 C10 127.55(14) . . ?
N2 C9 C8 122.13(14) . . ?
C10 C9 C8 110.32(13) . . ?
C11 C10 C9 117.96(14) . . ?
C11 C10 C14 135.08(14) . . ?
C9 C10 C14 106.96(12) . . ?
C10 C11 C12 116.19(15) . . ?
C10 C11 H11 121.9 . . ?
C12 C11 H11 121.9 . . ?
C13 C12 C11 121.45(15) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
N2 C13 C12 122.33(15) . . ?
N2 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
O1 C14 C7 127.52(14) . . ?
O1 C14 C10 127.08(14) . . ?
C7 C14 C10 105.40(12) . . ?
F1 B1 F1 111.6(5) 7_565 . ?
F1 B1 F2 119.3(5) 7_565 . ?
F1 B1 F2 110.2(2) . . ?
F1 B1 F2 110.2(2) 7_565 7_565 ?
F1 B1 F2 119.3(5) . 7_565 ?
F2 B1 F2 10.0(6) . 7_565 ?
F1 B1 F3 112.51(17) 7_565 7_565 ?
F1 B1 F3 91.66(19) . 7_565 ?
F2 B1 F3 108.03(15) . 7_565 ?
F2 B1 F3 110.29(14) 7_565 7_565 ?
F1 B1 F3 91.66(19) 7_565 . ?
F1 B1 F3 112.51(17) . . ?
F2 B1 F3 110.29(14) . . ?
F2 B1 F3 108.03(15) 7_565 . ?
F3 B1 F3 24.7(2) 7_565 . ?
F1 B1 F4 15.40(19) 7_565 . ?
F1 B1 F4 108.55(14) . . ?
F2 B1 F4 108.7(2) . . ?
F2 B1 F4 100.7(4) 7_565 . ?
F3 B1 F4 127.89(18) 7_565 . ?
F3 B1 F4 106.42(16) . . ?
F1 B1 F4 108.55(14) 7_565 7_565 ?
F1 B1 F4 15.40(19) . 7_565 ?
F2 B1 F4 100.7(4) . 7_565 ?
F2 B1 F4 108.7(2) 7_565 7_565 ?
F3 B1 F4 106.42(16) 7_565 7_565 ?
F3 B1 F4 127.89(18) . 7_565 ?
F4 B1 F4 101.6(4) . 7_565 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 C1 2.1123(18) . yes
Pd1 C3 2.1277(19) . yes
Pd1 C2 2.150(2) 7_565 yes
Pd1 C2 2.150(2) . yes
Pd1 N2 2.1712(14) . yes
Pd1 N1 2.1742(13) . yes
O1 C14 1.2053(18) . ?
N1 C8 1.3278(18) . ?
N1 C4 1.355(2) . ?
N2 C9 1.3294(19) . ?
N2 C13 1.355(2) . ?
C1 C2 1.444(3) . ?
C1 C2 1.444(3) 7_565 ?
C1 H1A 0.9699(11) . ?
C1 H1B 0.9700(11) . ?
C2 C3 1.390(3) . ?
C2 H2 1.0000 . ?
C3 C2 1.390(3) 7_565 ?
C3 H3A 0.9700(11) . ?
C3 H3B 0.9699(11) . ?
C4 C5 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3854(19) . ?
C7 C14 1.512(2) . ?
C8 C9 1.450(2) . ?
C9 C10 1.385(2) . ?
C10 C11 1.385(2) . ?
C10 C14 1.516(2) . ?
C11 C12 1.401(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
F1 B1 1.3860(19) . ?
F2 B1 1.3932(16) . ?
F3 B1 1.3964(16) . ?
F4 B1 1.4059(17) . ?
B1 F1 1.3860(19) 7_565 ?
B1 F2 1.3932(16) 7_565 ?
B1 F3 1.3964(16) 7_565 ?
B1 F4 1.4059(17) 7_565 ?
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
C1 Pd1 N1 C8 180.0 . .
C3 Pd1 N1 C8 180.0 . .
C2 Pd1 N1 C8 -152.87(10) 7_565 .
C2 Pd1 N1 C8 152.87(10) . .
N2 Pd1 N1 C8 0.0 . .
C1 Pd1 N1 C4 0.0 . .
C3 Pd1 N1 C4 0.0 . .
C2 Pd1 N1 C4 27.13(10) 7_565 .
C2 Pd1 N1 C4 -27.13(10) . .
N2 Pd1 N1 C4 180.0 . .
C1 Pd1 N2 C9 180.0 . .
C3 Pd1 N2 C9 180.0 . .
C2 Pd1 N2 C9 152.35(11) 7_565 .
C2 Pd1 N2 C9 -152.35(11) . .
N1 Pd1 N2 C9 0.0 . .
C1 Pd1 N2 C13 0.0 . .
C3 Pd1 N2 C13 0.0 . .
C2 Pd1 N2 C13 -27.65(11) 7_565 .
C2 Pd1 N2 C13 27.65(11) . .
N1 Pd1 N2 C13 180.0 . .
C3 Pd1 C1 C2 -30.42(12) . .
C2 Pd1 C1 C2 -60.8(2) 7_565 .
N2 Pd1 C1 C2 149.58(12) . .
N1 Pd1 C1 C2 -30.42(12) . .
C3 Pd1 C1 C2 30.42(12) . 7_565
C2 Pd1 C1 C2 60.8(2) . 7_565
N2 Pd1 C1 C2 -149.58(12) . 7_565
N1 Pd1 C1 C2 30.42(12) . 7_565
C2 C1 C2 C3 -25.9(2) 7_565 .
Pd1 C1 C2 C3 53.62(16) . .
C2 C1 C2 Pd1 -79.51(7) 7_565 .
C1 Pd1 C2 C3 -129.69(18) . .
C2 Pd1 C2 C3 -64.04(12) 7_565 .
N2 Pd1 C2 C3 -174.67(5) . .
N1 Pd1 C2 C3 45.86(16) . .
C3 Pd1 C2 C1 129.69(18) . .
C2 Pd1 C2 C1 65.65(11) 7_565 .
N2 Pd1 C2 C1 -44.98(16) . .
N1 Pd1 C2 C1 175.55(5) . .
C1 C2 C3 C2 26.2(2) . 7_565
Pd1 C2 C3 C2 79.15(8) . 7_565
C1 C2 C3 Pd1 -52.92(15) . .
C1 Pd1 C3 C2 -31.68(12) . 7_565
C2 Pd1 C3 C2 -63.4(2) . 7_565
N2 Pd1 C3 C2 -31.68(12) . 7_565
N1 Pd1 C3 C2 148.32(12) . 7_565
C1 Pd1 C3 C2 31.68(12) . .
C2 Pd1 C3 C2 63.4(2) 7_565 .
N2 Pd1 C3 C2 31.68(12) . .
N1 Pd1 C3 C2 -148.32(12) . .
C8 N1 C4 C5 0.0 . .
Pd1 N1 C4 C5 180.0 . .
N1 C4 C5 C6 0.0 . .
C4 C5 C6 C7 0.0 . .
C5 C6 C7 C8 0.0 . .
C5 C6 C7 C14 180.0 . .
C4 N1 C8 C7 0.0 . .
Pd1 N1 C8 C7 180.0 . .
C4 N1 C8 C9 180.0 . .
Pd1 N1 C8 C9 0.0 . .
C6 C7 C8 N1 0.0 . .
C14 C7 C8 N1 180.0 . .
C6 C7 C8 C9 180.0 . .
C14 C7 C8 C9 0.0 . .
C13 N2 C9 C10 0.0 . .
Pd1 N2 C9 C10 180.0 . .
C13 N2 C9 C8 180.0 . .
Pd1 N2 C9 C8 0.0 . .
N1 C8 C9 N2 0.0 . .
C7 C8 C9 N2 180.0 . .
N1 C8 C9 C10 180.0 . .
C7 C8 C9 C10 0.0 . .
N2 C9 C10 C11 0.0 . .
C8 C9 C10 C11 180.0 . .
N2 C9 C10 C14 180.0 . .
C8 C9 C10 C14 0.0 . .
C9 C10 C11 C12 0.0 . .
C14 C10 C11 C12 180.0 . .
C10 C11 C12 C13 0.0 . .
C9 N2 C13 C12 0.0 . .
Pd1 N2 C13 C12 180.0 . .
C11 C12 C13 N2 0.0 . .
C8 C7 C14 O1 180.0 . .
C6 C7 C14 O1 0.0 . .
C8 C7 C14 C10 0.0 . .
C6 C7 C14 C10 180.0 . .
C11 C10 C14 O1 0.0 . .
C9 C10 C14 O1 180.0 . .
C11 C10 C14 C7 180.0 . .
C9 C10 C14 C7 0.0 . .
