#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:29:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178784 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/38/4103867.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_4103867
loop_
_publ_author_name
'Steven P. Reade'
'Mary F. Mahon'
'Michael K. Whittlesey'
_publ_section_title
;
 Catalytic Hydrodefluorination of Aromatic Fluorocarbons by Ruthenium
 N-Heterocyclic Carbene Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1847
_journal_page_last               1861
_journal_paper_doi               10.1021/ja806545e
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C47 H46 F N2 O2 P Ru'
_chemical_formula_weight         821.90
_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                 93.960(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   44.3340(5)
_cell_length_b                   13.7120(2)
_cell_length_c                   13.3720(2)
_cell_measurement_reflns_used    60828
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     8109.54(19)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'Denzo & Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_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  0.0870
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_h_min       -57
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            68050
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.55
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Very-pale-buff
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             3408
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         9272
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0391
_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)+(0.0342P)²+12.6440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0906
_reflns_number_gt                6981
_reflns_number_total             9272
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja806545e_si_002_9.cif
_cod_data_source_block           supp_4_k07mkw26
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'None' changed to 'none'
according to the built-in table from CIF Core 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        8109.53(19)
_cod_database_code               4103867
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
Ru1 Ru 0.136980(4) 0.231232(15) 0.447411(14) 0.02063(7) Uani 1 1 d D
P1 P 0.150269(13) 0.32330(5) 0.30888(5) 0.02087(14) Uani 1 1 d .
F1 F 0.13258(4) 0.11812(11) 0.34497(11) 0.0333(4) Uani 1 1 d .
O1 O 0.07109(5) 0.30678(18) 0.41548(18) 0.0543(6) Uani 1 1 d .
O2 O 0.15134(5) 0.38555(15) 0.60058(15) 0.0412(5) Uani 1 1 d .
N1 N 0.15826(5) 0.06783(15) 0.59803(15) 0.0229(4) Uani 1 1 d .
N2 N 0.11203(4) 0.10226(15) 0.61895(15) 0.0244(4) Uani 1 1 d .
C1 C 0.09391(6) 0.2686(2) 0.4267(2) 0.0305(6) Uani 1 1 d .
C2 C 0.14507(6) 0.32756(19) 0.54032(19) 0.0264(6) Uani 1 1 d .
C3 C 0.13522(5) 0.12717(17) 0.56179(17) 0.0217(5) Uani 1 1 d .
C4 C 0.14934(6) 0.00768(19) 0.67441(19) 0.0281(6) Uani 1 1 d .
H4 H 0.1614 -0.0398 0.7102 0.034 Uiso 1 1 calc R
C5 C 0.12050(6) 0.0297(2) 0.68772(19) 0.0289(6) Uani 1 1 d .
H5 H 0.1082 0.0011 0.7351 0.035 Uiso 1 1 calc R
C6 C 0.08138(6) 0.1370(2) 0.60442(19) 0.0279(6) Uani 1 1 d .
C7 C 0.06240(6) 0.0917(2) 0.5301(2) 0.0307(6) Uani 1 1 d .
C8 C 0.03270(6) 0.1254(2) 0.5179(2) 0.0372(7) Uani 1 1 d .
H8 H 0.0193 0.0967 0.4676 0.045 Uiso 1 1 calc R
C9 C 0.02203(6) 0.1990(3) 0.5765(2) 0.0427(8) Uani 1 1 d .
C10 C 0.04152(7) 0.2407(2) 0.6504(2) 0.0415(7) Uani 1 1 d .
H10 H 0.0343 0.2912 0.6911 0.050 Uiso 1 1 calc R
C11 C 0.07154(6) 0.2101(2) 0.6661(2) 0.0331(6) Uani 1 1 d .
C12 C 0.07417(7) 0.0144(2) 0.4643(2) 0.0396(7) Uani 1 1 d .
H12A H 0.0884 0.0434 0.4199 0.059 Uiso 1 1 calc R
H12B H 0.0573 -0.0152 0.4240 0.059 Uiso 1 1 calc R
H12C H 0.0846 -0.0358 0.5060 0.059 Uiso 1 1 calc R
C13 C -0.01032(7) 0.2341(3) 0.5607(3) 0.0647(11) Uani 1 1 d .
H13A H -0.0151 0.2467 0.4893 0.097 Uiso 1 1 calc R
H13B H -0.0128 0.2942 0.5989 0.097 Uiso 1 1 calc R
H13C H -0.0240 0.1839 0.5838 0.097 Uiso 1 1 calc R
C14 C 0.09238(7) 0.2565(3) 0.7465(2) 0.0454(8) Uani 1 1 d .
H14A H 0.0979 0.2081 0.7985 0.068 Uiso 1 1 calc R
H14B H 0.0821 0.3114 0.7762 0.068 Uiso 1 1 calc R
H14C H 0.1107 0.2799 0.7169 0.068 Uiso 1 1 calc R
C15 C 0.18795(5) 0.06101(18) 0.55993(18) 0.0248(5) Uani 1 1 d .
C16 C 0.21115(6) 0.1189(2) 0.60239(19) 0.0280(6) Uani 1 1 d .
C17 C 0.23946(6) 0.1116(2) 0.5634(2) 0.0344(6) Uani 1 1 d .
H17 H 0.2556 0.1509 0.5910 0.041 Uiso 1 1 calc R
C18 C 0.24458(6) 0.0485(2) 0.4856(2) 0.0385(7) Uani 1 1 d .
C19 C 0.22121(7) -0.0095(2) 0.4479(2) 0.0364(7) Uani 1 1 d .
H19 H 0.2248 -0.0540 0.3956 0.044 Uiso 1 1 calc R
C20 C 0.19234(6) -0.0053(2) 0.48388(19) 0.0305(6) Uani 1 1 d .
C21 C 0.20599(6) 0.1892(2) 0.6855(2) 0.0361(6) Uani 1 1 d .
H21A H 0.1938 0.2442 0.6589 0.054 Uiso 1 1 calc R
H21B H 0.2255 0.2133 0.7144 0.054 Uiso 1 1 calc R
H21C H 0.1953 0.1561 0.7375 0.054 Uiso 1 1 calc R
C22 C 0.27538(7) 0.0443(3) 0.4431(3) 0.0541(9) Uani 1 1 d .
H22A H 0.2897 0.0110 0.4907 0.081 Uiso 1 1 calc R
H22B H 0.2825 0.1107 0.4316 0.081 Uiso 1 1 calc R
H22C H 0.2738 0.0086 0.3795 0.081 Uiso 1 1 calc R
C23 C 0.16677(7) -0.0691(2) 0.4424(2) 0.0401(7) Uani 1 1 d .
H23A H 0.1598 -0.1102 0.4961 0.060 Uiso 1 1 calc R
H23B H 0.1738 -0.1105 0.3891 0.060 Uiso 1 1 calc R
H23C H 0.1501 -0.0280 0.4152 0.060 Uiso 1 1 calc R
C24 C 0.12104(5) 0.33919(19) 0.20567(18) 0.0234(5) Uani 1 1 d .
C25 C 0.10693(6) 0.2556(2) 0.1661(2) 0.0359(7) Uani 1 1 d .
H25 H 0.1119 0.1936 0.1945 0.043 Uiso 1 1 calc R
C26 C 0.08558(7) 0.2628(2) 0.0850(2) 0.0417(7) Uani 1 1 d .
H26 H 0.0761 0.2055 0.0579 0.050 Uiso 1 1 calc R
C27 C 0.07812(6) 0.3528(2) 0.0438(2) 0.0378(7) Uani 1 1 d .
H27 H 0.0637 0.3573 -0.0120 0.045 Uiso 1 1 calc R
C28 C 0.09157(6) 0.4358(2) 0.0837(2) 0.0341(6) Uani 1 1 d .
H28 H 0.0862 0.4978 0.0561 0.041 Uiso 1 1 calc R
C29 C 0.11302(6) 0.4294(2) 0.16445(19) 0.0290(6) Uani 1 1 d .
H29 H 0.1223 0.4870 0.1916 0.035 Uiso 1 1 calc R
C30 C 0.16177(5) 0.44912(18) 0.33512(17) 0.0225(5) Uani 1 1 d .
C31 C 0.14209(6) 0.50811(19) 0.38539(19) 0.0293(6) Uani 1 1 d .
H31 H 0.1241 0.4809 0.4083 0.035 Uiso 1 1 calc R
C32 C 0.14844(7) 0.6055(2) 0.4021(2) 0.0338(6) Uani 1 1 d .
H32 H 0.1349 0.6450 0.4365 0.041 Uiso 1 1 calc R
C33 C 0.17460(7) 0.6455(2) 0.3688(2) 0.0358(7) Uani 1 1 d .
H33 H 0.1788 0.7129 0.3790 0.043 Uiso 1 1 calc R
C34 C 0.19445(6) 0.5881(2) 0.3211(2) 0.0332(6) Uani 1 1 d .
H34 H 0.2125 0.6158 0.2993 0.040 Uiso 1 1 calc R
C35 C 0.18840(6) 0.4899(2) 0.30430(19) 0.0279(6) Uani 1 1 d .
H35 H 0.2024 0.4505 0.2718 0.033 Uiso 1 1 calc R
C36 C 0.18095(5) 0.27119(19) 0.24047(18) 0.0233(5) Uani 1 1 d .
C37 C 0.18712(6) 0.3074(2) 0.1468(2) 0.0336(6) Uani 1 1 d .
H37 H 0.1753 0.3593 0.1179 0.040 Uiso 1 1 calc R
C38 C 0.21035(7) 0.2685(2) 0.0953(2) 0.0396(7) Uani 1 1 d .
H38 H 0.2149 0.2956 0.0327 0.047 Uiso 1 1 calc R
C39 C 0.22692(6) 0.1909(2) 0.1342(2) 0.0334(6) Uani 1 1 d .
H39 H 0.2425 0.1636 0.0979 0.040 Uiso 1 1 calc R
C40 C 0.22085(6) 0.1530(2) 0.2261(2) 0.0313(6) Uani 1 1 d .
H40 H 0.2322 0.0992 0.2528 0.038 Uiso 1 1 calc R
C41 C 0.19817(5) 0.19312(19) 0.2801(2) 0.0267(5) Uani 1 1 d .
H41 H 0.1944 0.1674 0.3440 0.032 Uiso 1 1 calc R
C42 C 0.02961(9) 0.1061(4) 0.2293(3) 0.0681(11) Uani 1 1 d .
H42 H 0.0503 0.1066 0.2148 0.082 Uiso 1 1 calc R
C43 C 0.01503(9) 0.0200(3) 0.2392(3) 0.0653(11) Uani 1 1 d .
H43 H 0.0254 -0.0399 0.2313 0.078 Uiso 1 1 calc R
C44 C 0.01483(10) 0.1907(3) 0.2400(3) 0.0730(13) Uani 1 1 d .
H44 H 0.0252 0.2509 0.2335 0.088 Uiso 1 1 calc R
C45 C 0.01376(11) 0.4799(4) 0.1633(4) 0.0906(15) Uani 1 1 d .
H45 H 0.0235 0.4788 0.1022 0.109 Uiso 1 1 calc R
C46 C 0.03085(10) 0.4809(4) 0.2523(4) 0.0788(13) Uani 1 1 d .
H46 H 0.0523 0.4819 0.2529 0.095 Uiso 1 1 calc R
C47 C -0.01722(10) 0.4805(3) 0.1606(4) 0.0769(12) Uani 1 1 d .
H47 H -0.0289 0.4806 0.0983 0.092 Uiso 1 1 calc R
H1 H 0.1728(2) 0.2201(19) 0.4653(19) 0.023(7) Uiso 1 1 d D
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 '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
H1 Ru1 C2 79.7(9) . .
H1 Ru1 C1 170.5(9) . .
C2 Ru1 C1 92.88(11) . .
H1 Ru1 F1 94.3(9) . .
C2 Ru1 F1 173.94(9) . .
C1 Ru1 F1 93.17(9) . .
H1 Ru1 C3 85.0(9) . .
C2 Ru1 C3 90.65(10) . .
C1 Ru1 C3 101.20(10) . .
F1 Ru1 C3 88.07(8) . .
H1 Ru1 P1 82.4(9) . .
C2 Ru1 P1 95.70(8) . .
C1 Ru1 P1 92.44(8) . .
F1 Ru1 P1 84.15(4) . .
C3 Ru1 P1 164.65(7) . .
C30 P1 C36 104.89(11) . .
C30 P1 C24 101.83(11) . .
C36 P1 C24 100.37(11) . .
C30 P1 Ru1 115.97(8) . .
C36 P1 Ru1 114.73(8) . .
C24 P1 Ru1 116.94(8) . .
C3 N1 C4 111.7(2) . .
C3 N1 C15 126.1(2) . .
C4 N1 C15 122.1(2) . .
C3 N2 C5 111.7(2) . .
C3 N2 C6 125.5(2) . .
C5 N2 C6 122.4(2) . .
O1 C1 Ru1 167.6(3) . .
O2 C2 Ru1 176.7(2) . .
N2 C3 N1 103.0(2) . .
N2 C3 Ru1 130.20(17) . .
N1 C3 Ru1 126.77(17) . .
C5 C4 N1 106.7(2) . .
C4 C5 N2 106.9(2) . .
C11 C6 C7 122.9(2) . .
C11 C6 N2 119.4(2) . .
C7 C6 N2 117.6(2) . .
C8 C7 C6 116.9(3) . .
C8 C7 C12 122.1(3) . .
C6 C7 C12 121.0(2) . .
C9 C8 C7 122.2(3) . .
C8 C9 C10 118.9(3) . .
C8 C9 C13 120.7(3) . .
C10 C9 C13 120.3(3) . .
C9 C10 C11 121.5(3) . .
C6 C11 C10 117.6(3) . .
C6 C11 C14 121.7(2) . .
C10 C11 C14 120.7(3) . .
C20 C15 C16 122.5(2) . .
C20 C15 N1 118.5(2) . .
C16 C15 N1 119.0(2) . .
C15 C16 C17 117.8(2) . .
C15 C16 C21 121.6(2) . .
C17 C16 C21 120.6(2) . .
C18 C17 C16 121.6(3) . .
C19 C18 C17 118.6(3) . .
C19 C18 C22 121.1(3) . .
C17 C18 C22 120.3(3) . .
C18 C19 C20 122.3(3) . .
C15 C20 C19 117.1(3) . .
C15 C20 C23 120.7(2) . .
C19 C20 C23 122.2(3) . .
C29 C24 C25 119.1(2) . .
C29 C24 P1 123.40(19) . .
C25 C24 P1 117.5(2) . .
C26 C25 C24 120.1(3) . .
C27 C26 C25 120.3(3) . .
C28 C27 C26 119.9(3) . .
C27 C28 C29 120.2(3) . .
C24 C29 C28 120.4(3) . .
C35 C30 C31 118.7(2) . .
C35 C30 P1 123.58(19) . .
C31 C30 P1 117.68(19) . .
C32 C31 C30 120.8(2) . .
C31 C32 C33 119.8(3) . .
C34 C33 C32 120.1(3) . .
C33 C34 C35 120.6(3) . .
C34 C35 C30 120.0(2) . .
C37 C36 C41 118.6(2) . .
C37 C36 P1 120.5(2) . .
C41 C36 P1 120.88(19) . .
C38 C37 C36 120.6(3) . .
C39 C38 C37 120.4(3) . .
C38 C39 C40 119.8(3) . .
C39 C40 C41 120.4(3) . .
C40 C41 C36 120.1(2) . .
C44 C42 C43 120.1(4) . .
C42 C43 C43 119.5(3) . 2
C42 C44 C44 120.4(3) . 2
C46 C45 C47 121.1(4) . .
C47 C46 C45 119.9(4) 2 .
C46 C47 C45 119.0(5) 2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ru1 H1 1.598(9) .
Ru1 C2 1.832(3) .
Ru1 C1 1.978(3) .
Ru1 F1 2.0697(14) .
Ru1 C3 2.097(2) .
Ru1 P1 2.3502(6) .
P1 C30 1.826(2) .
P1 C36 1.836(2) .
P1 C24 1.840(2) .
O1 C1 1.140(3) .
O2 C2 1.152(3) .
N1 C3 1.368(3) .
N1 C4 1.391(3) .
N1 C15 1.447(3) .
N2 C3 1.366(3) .
N2 C5 1.389(3) .
N2 C6 1.440(3) .
C4 C5 1.338(4) .
C6 C11 1.388(4) .
C6 C7 1.402(4) .
C7 C8 1.394(4) .
C7 C12 1.494(4) .
C8 C9 1.382(5) .
C9 C10 1.390(4) .
C9 C13 1.513(4) .
C10 C11 1.397(4) .
C11 C14 1.509(4) .
C15 C20 1.388(4) .
C15 C16 1.389(4) .
C16 C17 1.396(4) .
C16 C21 1.501(4) .
C17 C18 1.384(4) .
C18 C19 1.374(4) .
C18 C22 1.516(4) .
C19 C20 1.399(4) .
C20 C23 1.507(4) .
C24 C29 1.390(4) .
C24 C25 1.392(4) .
C25 C26 1.393(4) .
C26 C27 1.382(4) .
C27 C28 1.376(4) .
C28 C29 1.391(4) .
C30 C35 1.394(3) .
C30 C31 1.396(4) .
C31 C32 1.380(4) .
C32 C33 1.384(4) .
C33 C34 1.371(4) .
C34 C35 1.388(4) .
C36 C37 1.392(4) .
C36 C41 1.398(4) .
C37 C38 1.384(4) .
C38 C39 1.375(4) .
C39 C40 1.377(4) .
C40 C41 1.391(4) .
C42 C44 1.345(6) .
C42 C43 1.357(6) .
C43 C43 1.383(8) 2
C44 C44 1.360(9) 2
C45 C46 1.366(7) .
C45 C47 1.372(6) .
C46 C47 1.349(6) 2
C47 C46 1.349(6) 2
