#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:41:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178577 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/87/4068718.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_4068718
loop_
_publ_author_name
'Gu, Shaojin'
'Chen, Wanzhi'
_publ_section_title
;
 Pincer Complexes of Palladium- and Nickel-Containing
 3-Butyl-1-(1,10-phenanthrolin-2-yl)imidazolylidene as Efficient Aqueous
 Sonogashira and Kumada Coupling Reactions
;
_journal_issue                   3
_journal_name_full               Organometallics
_journal_page_first              909
_journal_paper_doi               10.1021/om801056v
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C19 H18 Cl F6 N4 P Pd'
_chemical_formula_weight         589.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.651(2)
_cell_angle_beta                 94.4560(10)
_cell_angle_gamma                90.4430(10)
_cell_formula_units_Z            2
_cell_length_a                   8.8503(13)
_cell_length_b                   10.0325(17)
_cell_length_c                   12.294(2)
_cell_measurement_temperature    298(2)
_cell_volume                     1072.7(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(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       '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  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5551
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    1.131
_exptl_absorpt_correction_T_max  0.7425
_exptl_absorpt_correction_T_min  0.6128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.824
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.853
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0362
_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)+(0.0700P)²+0.7172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                3075
_reflns_number_total             3713
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om801056v_si_001.cif
_cod_data_source_block           080711d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1072.6(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4068718
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.60509(3) 0.89391(3) 0.57257(3) 0.03897(14) Uani 1 1 d .
Cl1 Cl 0.76986(14) 0.84612(14) 0.43797(10) 0.0562(3) Uani 1 1 d .
P1 P 0.86552(14) 0.71142(14) 0.83633(11) 0.0528(3) Uani 1 1 d .
F1 F 0.6946(4) 0.7441(5) 0.8039(4) 0.1009(13) Uani 1 1 d .
F2 F 1.0366(4) 0.6876(4) 0.8707(3) 0.0939(12) Uani 1 1 d .
F3 F 0.8232(4) 0.7011(5) 0.9567(3) 0.1073(14) Uani 1 1 d .
F4 F 0.8338(6) 0.5576(4) 0.7982(5) 0.1328(18) Uani 1 1 d .
F5 F 0.9087(5) 0.7316(6) 0.7193(3) 0.1275(18) Uani 1 1 d .
F6 F 0.8981(6) 0.8684(4) 0.8758(5) 0.1300(17) Uani 1 1 d .
N1 N 0.3095(4) 0.7947(4) 0.5860(3) 0.0446(9) Uani 1 1 d .
N2 N 0.3690(4) 0.6879(4) 0.4291(3) 0.0441(9) Uani 1 1 d .
N3 N 0.4720(4) 0.9393(3) 0.6925(3) 0.0371(8) Uani 1 1 d .
N4 N 0.7476(4) 1.0354(4) 0.6830(3) 0.0407(8) Uani 1 1 d .
C1 C 0.4240(5) 0.7790(4) 0.5152(4) 0.0403(10) Uani 1 1 d .
C2 C 0.2241(5) 0.6457(5) 0.4449(5) 0.0571(13) Uani 1 1 d .
H2 H 0.1638 0.5823 0.3963 0.068 Uiso 1 1 calc R
C3 C 0.1862(5) 0.7118(5) 0.5418(5) 0.0556(12) Uani 1 1 d .
H3 H 0.0953 0.7038 0.5735 0.067 Uiso 1 1 calc R
C4 C 0.3352(5) 0.8855(4) 0.6849(4) 0.0425(10) Uani 1 1 d .
C5 C 0.2391(5) 0.9205(5) 0.7702(4) 0.0495(11) Uani 1 1 d .
H5 H 0.1428 0.8813 0.7661 0.059 Uiso 1 1 calc R
C6 C 0.2919(6) 1.0147(5) 0.8601(4) 0.0522(12) Uani 1 1 d .
H6 H 0.2299 1.0395 0.9175 0.063 Uiso 1 1 calc R
C7 C 0.4371(5) 1.0742(5) 0.8671(4) 0.0481(11) Uani 1 1 d .
C8 C 0.5254(5) 1.0318(4) 0.7801(3) 0.0397(10) Uani 1 1 d .
C9 C 0.6749(5) 1.0822(4) 0.7748(4) 0.0397(9) Uani 1 1 d .
C10 C 0.7369(5) 1.1776(5) 0.8628(4) 0.0475(11) Uani 1 1 d .
C11 C 0.8862(5) 1.2256(5) 0.8536(4) 0.0540(12) Uani 1 1 d .
H11 H 0.9345 1.2884 0.9100 0.065 Uiso 1 1 calc R
C12 C 0.9569(6) 1.1783(6) 0.7614(4) 0.0576(13) Uani 1 1 d .
H12 H 1.0540 1.2100 0.7541 0.069 Uiso 1 1 calc R
C13 C 0.8854(5) 1.0822(5) 0.6770(4) 0.0485(11) Uani 1 1 d .
H13 H 0.9369 1.0505 0.6150 0.058 Uiso 1 1 calc R
C14 C 0.5058(6) 1.1723(6) 0.9561(4) 0.0556(12) Uani 1 1 d .
H14 H 0.4515 1.2030 1.0168 0.067 Uiso 1 1 calc R
C15 C 0.6481(6) 1.2206(6) 0.9531(4) 0.0573(13) Uani 1 1 d .
H15 H 0.6891 1.2842 1.0121 0.069 Uiso 1 1 calc R
C16 C 0.4501(5) 0.6406(5) 0.3307(4) 0.0469(11) Uani 1 1 d .
H16A H 0.5184 0.7121 0.3193 0.056 Uiso 1 1 calc R
H16B H 0.3773 0.6222 0.2666 0.056 Uiso 1 1 calc R
C17 C 0.5399(7) 0.5150(5) 0.3388(4) 0.0600(13) Uani 1 1 d .
H17A H 0.4739 0.4453 0.3562 0.072 Uiso 1 1 calc R
H17B H 0.6195 0.5351 0.3984 0.072 Uiso 1 1 calc R
C18 C 0.6106(7) 0.4630(6) 0.2304(5) 0.0707(16) Uani 1 1 d .
H18A H 0.6595 0.3782 0.2369 0.085 Uiso 1 1 calc R
H18B H 0.5300 0.4442 0.1715 0.085 Uiso 1 1 calc R
C19 C 0.7234(8) 0.5565(7) 0.1980(7) 0.095(2) Uani 1 1 d .
H19A H 0.6756 0.6398 0.1884 0.143 Uiso 1 1 calc R
H19B H 0.7624 0.5158 0.1297 0.143 Uiso 1 1 calc R
H19C H 0.8051 0.5745 0.2548 0.143 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'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
N3 Pd1 C1 78.42(16)
N3 Pd1 N4 80.36(14)
C1 Pd1 N4 158.78(16)
N3 Pd1 Cl1 177.25(11)
C1 Pd1 Cl1 104.26(13)
N4 Pd1 Cl1 96.96(10)
F4 P1 F5 92.7(3)
F4 P1 F2 91.9(3)
F5 P1 F2 89.9(2)
F4 P1 F3 91.0(3)
F5 P1 F3 176.3(3)
F2 P1 F3 90.3(2)
F4 P1 F1 91.2(3)
F5 P1 F1 90.0(2)
F2 P1 F1 176.8(3)
F3 P1 F1 89.6(2)
F4 P1 F6 179.8(3)
F5 P1 F6 87.5(3)
F2 P1 F6 88.0(3)
F3 P1 F6 88.8(3)
F1 P1 F6 88.9(3)
C1 N1 C3 110.3(4)
C1 N1 C4 117.7(4)
C3 N1 C4 132.0(4)
C1 N2 C2 110.6(4)
C1 N2 C16 124.6(4)
C2 N2 C16 124.7(4)
C4 N3 C8 122.2(4)
C4 N3 Pd1 120.8(3)
C8 N3 Pd1 116.9(3)
C13 N4 C9 118.1(4)
C13 N4 Pd1 132.2(3)
C9 N4 Pd1 109.7(3)
N2 C1 N1 104.7(4)
N2 C1 Pd1 142.4(3)
N1 C1 Pd1 112.9(3)
C3 C2 N2 108.1(4)
C3 C2 H2 126.0
N2 C2 H2 126.0
C2 C3 N1 106.3(4)
C2 C3 H3 126.9
N1 C3 H3 126.9
N3 C4 N1 110.1(4)
N3 C4 C5 120.6(4)
N1 C4 C5 129.3(4)
C6 C5 C4 117.8(4)
C6 C5 H5 121.1
C4 C5 H5 121.1
C5 C6 C7 121.5(4)
C5 C6 H6 119.2
C7 C6 H6 119.2
C8 C7 C6 116.7(4)
C8 C7 C14 116.2(4)
C6 C7 C14 127.0(4)
N3 C8 C7 121.1(4)
N3 C8 C9 115.4(4)
C7 C8 C9 123.6(4)
N4 C9 C10 124.0(4)
N4 C9 C8 117.7(4)
C10 C9 C8 118.3(4)
C9 C10 C11 116.3(4)
C9 C10 C15 118.7(4)
C11 C10 C15 125.0(4)
C12 C11 C10 119.0(5)
C12 C11 H11 120.5
C10 C11 H11 120.5
C11 C12 C13 120.7(5)
C11 C12 H12 119.7
C13 C12 H12 119.7
N4 C13 C12 121.9(4)
N4 C13 H13 119.0
C12 C13 H13 119.0
C15 C14 C7 121.1(4)
C15 C14 H14 119.4
C7 C14 H14 119.4
C14 C15 C10 122.1(5)
C14 C15 H15 118.9
C10 C15 H15 118.9
N2 C16 C17 113.4(4)
N2 C16 H16A 108.9
C17 C16 H16A 108.9
N2 C16 H16B 108.9
C17 C16 H16B 108.9
H16A C16 H16B 107.7
C16 C17 C18 111.3(4)
C16 C17 H17A 109.4
C18 C17 H17A 109.4
C16 C17 H17B 109.4
C18 C17 H17B 109.4
H17A C17 H17B 108.0
C19 C18 C17 115.0(5)
C19 C18 H18A 108.5
C17 C18 H18A 108.5
C19 C18 H18B 108.5
C17 C18 H18B 108.5
H18A C18 H18B 107.5
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 N3 1.954(3)
Pd1 C1 1.980(4)
Pd1 N4 2.123(4)
Pd1 Cl1 2.2835(11)
P1 F4 1.553(4)
P1 F5 1.561(4)
P1 F2 1.571(3)
P1 F3 1.574(4)
P1 F1 1.585(4)
P1 F6 1.585(5)
N1 C1 1.379(6)
N1 C3 1.386(6)
N1 C4 1.394(6)
N2 C1 1.334(6)
N2 C2 1.386(6)
N2 C16 1.467(6)
N3 C4 1.312(6)
N3 C8 1.350(6)
N4 C13 1.315(6)
N4 C9 1.360(5)
C2 C3 1.331(7)
C2 H2 0.9300
C3 H3 0.9300
C4 C5 1.402(6)
C5 C6 1.377(7)
C5 H5 0.9300
C6 C7 1.403(7)
C6 H6 0.9300
C7 C8 1.384(6)
C7 C14 1.436(7)
C8 C9 1.423(6)
C9 C10 1.392(6)
C10 C11 1.422(7)
C10 C15 1.421(7)
C11 C12 1.355(7)
C11 H11 0.9300
C12 C13 1.400(7)
C12 H12 0.9300
C13 H13 0.9300
C14 C15 1.351(7)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.508(7)
C16 H16A 0.9700
C16 H16B 0.9700
C17 C18 1.531(7)
C17 H17A 0.9700
C17 H17B 0.9700
C18 C19 1.486(8)
C18 H18A 0.9700
C18 H18B 0.9700
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
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
C1 Pd1 N3 C4 -1.9(3)
N4 Pd1 N3 C4 178.4(3)
Cl1 Pd1 N3 C4 -170(2)
C1 Pd1 N3 C8 -179.2(3)
N4 Pd1 N3 C8 1.1(3)
Cl1 Pd1 N3 C8 13(2)
N3 Pd1 N4 C13 179.8(4)
C1 Pd1 N4 C13 179.1(4)
Cl1 Pd1 N4 C13 0.4(4)
N3 Pd1 N4 C9 -0.4(3)
C1 Pd1 N4 C9 -1.1(6)
Cl1 Pd1 N4 C9 -179.8(3)
C2 N2 C1 N1 -0.5(5)
C16 N2 C1 N1 178.6(4)
C2 N2 C1 Pd1 179.7(4)
C16 N2 C1 Pd1 -1.1(8)
C3 N1 C1 N2 0.3(5)
C4 N1 C1 N2 180.0(4)
C3 N1 C1 Pd1 -179.8(3)
C4 N1 C1 Pd1 -0.1(5)
N3 Pd1 C1 N2 -179.2(6)
N4 Pd1 C1 N2 -178.6(4)
Cl1 Pd1 C1 N2 0.2(6)
N3 Pd1 C1 N1 1.0(3)
N4 Pd1 C1 N1 1.7(6)
Cl1 Pd1 C1 N1 -179.6(3)
C1 N2 C2 C3 0.5(6)
C16 N2 C2 C3 -178.6(4)
N2 C2 C3 N1 -0.3(6)
C1 N1 C3 C2 0.0(6)
C4 N1 C3 C2 -179.6(5)
C8 N3 C4 N1 179.3(4)
Pd1 N3 C4 N1 2.2(5)
C8 N3 C4 C5 -1.6(6)
Pd1 N3 C4 C5 -178.7(3)
C1 N1 C4 N3 -1.3(6)
C3 N1 C4 N3 178.3(5)
C1 N1 C4 C5 179.7(4)
C3 N1 C4 C5 -0.7(8)
N3 C4 C5 C6 1.4(7)
N1 C4 C5 C6 -179.7(5)
C4 C5 C6 C7 -0.1(7)
C5 C6 C7 C8 -1.0(7)
C5 C6 C7 C14 -179.5(5)
C4 N3 C8 C7 0.3(6)
Pd1 N3 C8 C7 177.5(3)
C4 N3 C8 C9 -178.8(4)
Pd1 N3 C8 C9 -1.6(5)
C6 C7 C8 N3 1.0(6)
C14 C7 C8 N3 179.6(4)
C6 C7 C8 C9 -179.9(4)
C14 C7 C8 C9 -1.3(7)
C13 N4 C9 C10 0.5(7)
Pd1 N4 C9 C10 -179.3(4)
C13 N4 C9 C8 179.5(4)
Pd1 N4 C9 C8 -0.3(5)
N3 C8 C9 N4 1.2(6)
C7 C8 C9 N4 -177.9(4)
N3 C8 C9 C10 -179.7(4)
C7 C8 C9 C10 1.2(7)
N4 C9 C10 C11 -0.7(7)
C8 C9 C10 C11 -179.7(4)
N4 C9 C10 C15 178.6(4)
C8 C9 C10 C15 -0.4(7)
C9 C10 C11 C12 0.9(7)
C15 C10 C11 C12 -178.4(5)
C10 C11 C12 C13 -0.9(8)
C9 N4 C13 C12 -0.6(7)
Pd1 N4 C13 C12 179.2(3)
C11 C12 C13 N4 0.8(8)
C8 C7 C14 C15 0.8(7)
C6 C7 C14 C15 179.2(5)
C7 C14 C15 C10 -0.1(8)
C9 C10 C15 C14 -0.1(8)
C11 C10 C15 C14 179.1(5)
C1 N2 C16 C17 92.5(5)
C2 N2 C16 C17 -88.5(6)
N2 C16 C17 C18 175.0(4)
C16 C17 C18 C19 63.3(7)
