#------------------------------------------------------------------------------
#$Date: 2016-03-21 08:38:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178609 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/20/4072014.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_4072014
loop_
_publ_author_name
'Grushin, Vladimir V.'
'Marshall, William J.'
_publ_section_title
;
 Fluorination of Nonactivated Haloarenes via Arynes under Mild Conditions,
 Resulting from Further Studies toward Ar−F Reductive Elimination
 from Palladium(II)
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              4825
_journal_paper_doi               10.1021/om800520e
_journal_volume                  27
_journal_year                    2008
_chemical_formula_sum            'C18 H29 I N6 P2 Pd'
_chemical_formula_weight         624.71
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 114.0543(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.064(3)
_cell_length_b                   11.8607(16)
_cell_length_c                   10.9238(15)
_cell_measurement_temperature    293(2)
_cell_volume                     2255.5(6)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18092
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    2.350
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0216
_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)+(0.0228P)²+2.1012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0510
_refine_ls_wR_factor_ref         0.0546
_reflns_number_gt                2315
_reflns_number_total             2810
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om800520e-file002.cif
_cod_data_source_block           07148
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2255.5(5)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4072014
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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
Pd1 Pd 0.0000 1.118915(18) 0.7500 0.01929(7) Uani 1 2 d S
I1 I 0.0000 0.890782(16) 0.7500 0.02767(7) Uani 1 2 d S
P1 P -0.11189(3) 1.13285(4) 0.77873(5) 0.01944(12) Uani 1 1 d .
N1 N -0.22304(11) 1.03817(16) 0.84661(19) 0.0250(4) Uani 1 1 d .
C1 C 0.0000 1.2896(3) 0.7500 0.0237(6) Uani 1 2 d S
N2 N -0.26898(10) 1.15222(16) 0.63962(18) 0.0239(4) Uani 1 1 d .
C2 C 0.04152(15) 1.3504(2) 0.8664(3) 0.0342(6) Uani 1 1 d .
H2A H 0.0695 1.3121 0.9457 0.041 Uiso 1 1 calc R
N3 N -0.21133(12) 1.24541(16) 0.86109(19) 0.0284(4) Uani 1 1 d .
C3 C 0.04162(18) 1.4677(2) 0.8655(3) 0.0479(8) Uani 1 1 d .
H3A H 0.0701 1.5069 0.9438 0.057 Uiso 1 1 calc R
C4 C 0.0000 1.5259(3) 0.7500 0.0572(13) Uani 1 2 d S
H4A H 0.0000 1.6044 0.7500 0.069 Uiso 1 2 calc SR
C5 C -0.14541(14) 1.01670(17) 0.8532(2) 0.0239(5) Uani 1 1 d .
H5A H -0.1458 0.9472 0.8061 0.029 Uiso 1 1 calc R
H5B H -0.1099 1.0072 0.9462 0.029 Uiso 1 1 calc R
C6 C -0.19723(12) 1.14600(18) 0.6197(2) 0.0214(4) Uani 1 1 d .
H6A H -0.1924 1.2133 0.5734 0.026 Uiso 1 1 calc R
H6B H -0.1996 1.0816 0.5634 0.026 Uiso 1 1 calc R
C7 C -0.13250(14) 1.25173(19) 0.8684(2) 0.0267(5) Uani 1 1 d .
H7A H -0.0962 1.2506 0.9616 0.032 Uiso 1 1 calc R
H7B H -0.1259 1.3223 0.8293 0.032 Uiso 1 1 calc R
C8 C -0.27925(13) 1.0509(2) 0.7078(2) 0.0265(5) Uani 1 1 d .
H8A H -0.3303 1.0526 0.7071 0.032 Uiso 1 1 calc R
H8B H -0.2764 0.9851 0.6573 0.032 Uiso 1 1 calc R
C9 C -0.22407(15) 1.1411(2) 0.9212(2) 0.0308(5) Uani 1 1 d .
H9A H -0.2733 1.1461 0.9273 0.037 Uiso 1 1 calc R
H9B H -0.1847 1.1347 1.0116 0.037 Uiso 1 1 calc R
C10 C -0.26816(14) 1.25056(18) 0.7223(2) 0.0274(5) Uani 1 1 d .
H10A H -0.2584 1.3175 0.6807 0.033 Uiso 1 1 calc R
H10B H -0.3187 1.2586 0.7226 0.033 Uiso 1 1 calc R
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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 '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
C1 Pd1 P1 85.851(15) . .
C1 Pd1 P1 85.853(15) . 2_556
P1 Pd1 P1 171.70(3) . 2_556
C1 Pd1 I1 180.000(1) . .
P1 Pd1 I1 94.149(15) . .
P1 Pd1 I1 94.147(14) 2_556 .
C6 P1 C5 98.51(10) . .
C6 P1 C7 97.96(10) . .
C5 P1 C7 98.59(10) . .
C6 P1 Pd1 113.09(7) . .
C5 P1 Pd1 121.20(8) . .
C7 P1 Pd1 122.69(8) . .
C8 N1 C9 108.57(18) . .
C8 N1 C5 111.41(17) . .
C9 N1 C5 110.83(19) . .
C2 C1 C2 117.6(3) 2_556 .
C2 C1 Pd1 121.18(15) 2_556 .
C2 C1 Pd1 121.19(15) . .
C8 N2 C10 107.92(17) . .
C8 N2 C6 110.98(17) . .
C10 N2 C6 110.63(17) . .
C3 C2 C1 120.9(3) . .
C10 N3 C9 108.15(19) . .
C10 N3 C7 111.23(17) . .
C9 N3 C7 111.70(18) . .
C4 C3 C2 120.5(3) . .
C3 C4 C3 119.5(4) . 2_556
N1 C5 P1 111.79(14) . .
N2 C6 P1 112.48(14) . .
N3 C7 P1 111.40(15) . .
N1 C8 N2 114.62(18) . .
N3 C9 N1 114.21(17) . .
N3 C10 N2 114.93(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 2.024(3) .
Pd1 P1 2.2850(6) .
Pd1 P1 2.2850(6) 2_556
Pd1 I1 2.7058(5) .
P1 C6 1.840(2) .
P1 C5 1.842(2) .
P1 C7 1.848(2) .
N1 C8 1.464(3) .
N1 C9 1.472(3) .
N1 C5 1.474(3) .
C1 C2 1.394(3) 2_556
C1 C2 1.394(3) .
N2 C8 1.469(3) .
N2 C10 1.471(3) .
N2 C6 1.472(3) .
C2 C3 1.391(3) .
N3 C10 1.462(3) .
N3 C9 1.467(3) .
N3 C7 1.474(3) .
C3 C4 1.372(4) .
C4 C3 1.372(4) 2_556
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 P1 C6 86.48(8) . .
P1 Pd1 P1 C6 86.48(8) 2_556 .
I1 Pd1 P1 C6 -93.52(8) . .
C1 Pd1 P1 C5 -157.02(9) . .
P1 Pd1 P1 C5 -157.02(9) 2_556 .
I1 Pd1 P1 C5 22.98(9) . .
C1 Pd1 P1 C7 -30.43(9) . .
P1 Pd1 P1 C7 -30.43(9) 2_556 .
I1 Pd1 P1 C7 149.57(9) . .
P1 Pd1 C1 C2 -83.99(12) . 2_556
P1 Pd1 C1 C2 96.01(12) 2_556 2_556
I1 Pd1 C1 C2 -77(100) . 2_556
P1 Pd1 C1 C2 96.02(12) . .
P1 Pd1 C1 C2 -83.98(12) 2_556 .
I1 Pd1 C1 C2 103(100) . .
C2 C1 C2 C3 -0.4(2) 2_556 .
Pd1 C1 C2 C3 179.6(2) . .
C1 C2 C3 C4 0.7(4) . .
C2 C3 C4 C3 -0.4(2) . 2_556
C8 N1 C5 P1 60.1(2) . .
C9 N1 C5 P1 -60.9(2) . .
C6 P1 C5 N1 -49.22(17) . .
C7 P1 C5 N1 50.23(18) . .
Pd1 P1 C5 N1 -172.88(12) . .
C8 N2 C6 P1 -59.7(2) . .
C10 N2 C6 P1 60.1(2) . .
C5 P1 C6 N2 49.37(17) . .
C7 P1 C6 N2 -50.62(17) . .
Pd1 P1 C6 N2 178.66(12) . .
C10 N3 C7 P1 -60.9(2) . .
C9 N3 C7 P1 60.1(2) . .
C6 P1 C7 N3 50.45(17) . .
C5 P1 C7 N3 -49.47(18) . .
Pd1 P1 C7 N3 174.53(11) . .
C9 N1 C8 N2 54.9(2) . .
C5 N1 C8 N2 -67.5(2) . .
C10 N2 C8 N1 -54.5(2) . .
C6 N2 C8 N1 66.9(2) . .
C10 N3 C9 N1 55.1(3) . .
C7 N3 C9 N1 -67.6(3) . .
C8 N1 C9 N3 -55.0(3) . .
C5 N1 C9 N3 67.7(3) . .
C9 N3 C10 N2 -55.5(2) . .
C7 N3 C10 N2 67.5(2) . .
C8 N2 C10 N3 55.0(2) . .
C6 N2 C10 N3 -66.5(2) . .
