#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/07/4080797.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_4080797
loop_
_publ_author_name
'Barrios-Francisco, Rigoberto'
'Balaraman, Ekambaram'
'Diskin-Posner, Yael'
'Leitus, Gregory'
'Shimon, Linda J. W.'
'Milstein, David'
_publ_section_title
;
 PNN Ruthenium Pincer Complexes Based on Phosphinated
 2,2′-Dipyridinemethane and 2,2′-Oxobispyridine.
 Metal--Ligand Cooperation in Cyclometalation and Catalysis
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              2973
_journal_paper_doi               10.1021/om400194w
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C25 H36 Cl N2 O P Ru, 0.5(C6 H6)'
_chemical_formula_sum            'C28 H39 Cl N2 O P Ru'
_chemical_formula_weight         587.10
_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                 99.703(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6739(5)
_cell_length_b                   12.5406(6)
_cell_length_c                   18.8822(10)
_cell_measurement_reflns_used    33833
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.9515
_cell_measurement_theta_min      2.402
_cell_volume                     2724.8(2)
_computing_cell_refinement       'APEX 2'
_computing_data_collection       'APEX 2'
_computing_data_reduction        'APEX 2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX - II Kappa CCD'
_diffrn_measurement_method       'omega and phi scan'
_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  0.0597
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            33123
_diffrn_reflns_theta_full        33.27
_diffrn_reflns_theta_max         33.27
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  0.9365
_exptl_absorpt_correction_T_min  0.6832
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker APEX 2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.288
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         10438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0390
_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)+(0.0303P)²+0.7656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0916
_reflns_number_gt                7184
_reflns_number_total             10438
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400194w_si_002.cif
_cod_data_source_block           complex_6b
_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 2.3.1 from 2005-06-27.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4080797
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
Ru1 Ru -0.000384(14) 0.627923(12) 0.247861(9) 0.01108(4) Uani 1 1 d .
H1 H 0.1432(18) 0.6003(17) 0.2860(12) 0.008(5) Uiso 1 1 d .
P2 P -0.02080(4) 0.45263(4) 0.21723(3) 0.01229(10) Uani 1 1 d .
N3 N -0.07966(14) 0.57611(14) 0.33848(9) 0.0129(3) Uani 1 1 d .
N4 N -0.00279(14) 0.78842(14) 0.29128(10) 0.0134(3) Uani 1 1 d .
Cl5 Cl -0.21127(5) 0.68104(4) 0.20065(3) 0.01854(11) Uani 1 1 d .
C6 C 0.0707(2) 0.66178(18) 0.17056(14) 0.0207(5) Uani 1 1 d .
O7 O 0.11779(17) 0.67885(15) 0.12572(10) 0.0324(4) Uani 1 1 d .
C8 C -0.01441(17) 0.86710(16) 0.24213(12) 0.0163(4) Uani 1 1 d .
H8 H -0.0070 0.8490 0.1942 0.020 Uiso 1 1 calc R
C9 C -0.03633(19) 0.97186(18) 0.25661(13) 0.0196(4) Uani 1 1 d .
H9 H -0.0408 1.0247 0.2202 0.024 Uiso 1 1 calc R
C10 C -0.05165(19) 0.99832(18) 0.32518(13) 0.0209(5) Uani 1 1 d .
H10 H -0.0687 1.0696 0.3370 0.025 Uiso 1 1 calc R
C11 C -0.04157(19) 0.91841(18) 0.37639(13) 0.0191(4) Uani 1 1 d .
H11 H -0.0532 0.9348 0.4238 0.023 Uiso 1 1 calc R
C12 C -0.01461(17) 0.81401(17) 0.35948(11) 0.0143(4) Uani 1 1 d .
C13 C 0.00524(18) 0.72656(17) 0.41672(11) 0.0148(4) Uani 1 1 d .
C14 C -0.08068(18) 0.63405(16) 0.39929(11) 0.0143(4) Uani 1 1 d .
C15 C -0.15671(18) 0.60765(17) 0.44602(12) 0.0173(4) Uani 1 1 d .
H15 H -0.1609 0.6514 0.4866 0.021 Uiso 1 1 calc R
C16 C -0.22636(18) 0.51754(18) 0.43342(12) 0.0184(4) Uani 1 1 d .
H16 H -0.2791 0.4998 0.4648 0.022 Uiso 1 1 calc R
C17 C -0.21791(18) 0.45429(18) 0.37491(12) 0.0170(4) Uani 1 1 d .
H17 H -0.2602 0.3894 0.3673 0.020 Uiso 1 1 calc R
C18 C -0.14627(17) 0.48720(16) 0.32717(11) 0.0138(4) Uani 1 1 d .
C19 C -0.14699(18) 0.42409(17) 0.25959(12) 0.0161(4) Uani 1 1 d .
H19A H -0.2187 0.4407 0.2253 0.019 Uiso 1 1 calc R
H19B H -0.1481 0.3471 0.2710 0.019 Uiso 1 1 calc R
C20 C 0.13439(18) 0.68896(19) 0.42594(12) 0.0190(4) Uani 1 1 d .
H20A H 0.1449 0.6199 0.4516 0.023 Uiso 1 1 calc R
H20B H 0.1595 0.6812 0.3787 0.023 Uiso 1 1 calc R
C21 C 0.2026(2) 0.7772(2) 0.47003(14) 0.0285(6) Uani 1 1 d .
H21A H 0.2304 0.8301 0.4379 0.034 Uiso 1 1 calc R
H21B H 0.2709 0.7469 0.5019 0.034 Uiso 1 1 calc R
C22 C 0.1208(2) 0.8302(2) 0.51457(13) 0.0252(5) Uani 1 1 d .
H22A H 0.1116 0.9070 0.5030 0.030 Uiso 1 1 calc R
H22B H 0.1505 0.8222 0.5666 0.030 Uiso 1 1 calc R
C23 C 0.0052(2) 0.77092(19) 0.49337(12) 0.0198(4) Uani 1 1 d .
H23A H -0.0610 0.8202 0.4935 0.024 Uiso 1 1 calc R
H23B H -0.0011 0.7120 0.5274 0.024 Uiso 1 1 calc R
C24 C -0.07114(18) 0.40924(17) 0.12122(12) 0.0161(4) Uani 1 1 d .
C25 C -0.1429(2) 0.30553(18) 0.11468(13) 0.0215(5) Uani 1 1 d .
H25A H -0.1682 0.2884 0.0638 0.032 Uiso 1 1 calc R
H25B H -0.2111 0.3150 0.1380 0.032 Uiso 1 1 calc R
H25C H -0.0950 0.2472 0.1381 0.032 Uiso 1 1 calc R
C26 C 0.0328(2) 0.39608(18) 0.08223(13) 0.0211(5) Uani 1 1 d .
H26A H 0.0049 0.3872 0.0306 0.032 Uiso 1 1 calc R
H26B H 0.0777 0.3331 0.1009 0.032 Uiso 1 1 calc R
H26C H 0.0823 0.4595 0.0902 0.032 Uiso 1 1 calc R
C27 C -0.14989(19) 0.49729(18) 0.08311(12) 0.0202(4) Uani 1 1 d .
H27A H -0.1052 0.5634 0.0828 0.030 Uiso 1 1 calc R
H27B H -0.2153 0.5092 0.1086 0.030 Uiso 1 1 calc R
H27C H -0.1795 0.4755 0.0336 0.030 Uiso 1 1 calc R
C28 C 0.09678(19) 0.36032(18) 0.26222(12) 0.0184(4) Uani 1 1 d .
C29 C 0.2151(2) 0.3905(2) 0.24223(14) 0.0258(5) Uani 1 1 d .
H29A H 0.2320 0.4655 0.2542 0.039 Uiso 1 1 calc R
H29B H 0.2127 0.3796 0.1906 0.039 Uiso 1 1 calc R
H29C H 0.2760 0.3455 0.2692 0.039 Uiso 1 1 calc R
C30 C 0.1065(2) 0.37463(19) 0.34395(13) 0.0226(5) Uani 1 1 d .
H30A H 0.1704 0.3307 0.3686 0.034 Uiso 1 1 calc R
H30B H 0.0336 0.3526 0.3588 0.034 Uiso 1 1 calc R
H30C H 0.1218 0.4497 0.3564 0.034 Uiso 1 1 calc R
C31 C 0.0716(2) 0.24189(18) 0.24618(15) 0.0281(5) Uani 1 1 d .
H31A H 0.1306 0.1983 0.2761 0.042 Uiso 1 1 calc R
H31B H 0.0737 0.2277 0.1954 0.042 Uiso 1 1 calc R
H31C H -0.0054 0.2240 0.2568 0.042 Uiso 1 1 calc R
C32 C 1.0059(3) 0.8917(2) 1.01281(18) 0.0363(7) Uani 1 1 d .
H32 H 1.0099 0.8171 1.0217 0.044 Uiso 1 1 calc R
C33 C 0.9369(2) 1.0384(3) 0.93721(15) 0.0345(6) Uani 1 1 d .
H33 H 0.8931 1.0648 0.8938 0.041 Uiso 1 1 calc R
C34 C 0.9430(2) 0.9305(2) 0.94985(16) 0.0346(6) Uani 1 1 d .
H34 H 0.9036 0.8826 0.9151 0.042 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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 '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
C6 Ru1 N4 96.97(8) . .
C6 Ru1 N3 175.81(8) . .
N4 Ru1 N3 86.89(7) . .
C6 Ru1 P2 93.61(7) . .
N4 Ru1 P2 169.20(5) . .
N3 Ru1 P2 82.60(5) . .
C6 Ru1 Cl5 101.47(7) . .
N4 Ru1 Cl5 79.51(5) . .
N3 Ru1 Cl5 80.81(5) . .
P2 Ru1 Cl5 96.282(18) . .
C6 Ru1 H1 81.0(8) . .
N4 Ru1 H1 95.8(7) . .
N3 Ru1 H1 97.0(7) . .
P2 Ru1 H1 88.0(7) . .
Cl5 Ru1 H1 174.9(7) . .
C19 P2 C28 105.19(10) . .
C19 P2 C24 102.74(10) . .
C28 P2 C24 109.92(10) . .
C19 P2 Ru1 97.80(7) . .
C28 P2 Ru1 116.21(7) . .
C24 P2 Ru1 121.64(7) . .
C18 N3 C14 119.07(17) . .
C18 N3 Ru1 115.47(13) . .
C14 N3 Ru1 124.69(14) . .
C8 N4 C12 117.82(18) . .
C8 N4 Ru1 115.13(14) . .
C12 N4 Ru1 125.91(14) . .
O7 C6 Ru1 176.5(2) . .
N4 C8 C9 124.3(2) . .
N4 C8 H8 117.8 . .
C9 C8 H8 117.8 . .
C10 C9 C8 118.4(2) . .
C10 C9 H9 120.8 . .
C8 C9 H9 120.8 . .
C9 C10 C11 118.2(2) . .
C9 C10 H10 120.9 . .
C11 C10 H10 120.9 . .
C10 C11 C12 121.0(2) . .
C10 C11 H11 119.5 . .
C12 C11 H11 119.5 . .
N4 C12 C11 120.1(2) . .
N4 C12 C13 118.26(18) . .
C11 C12 C13 121.59(19) . .
C12 C13 C14 112.04(17) . .
C12 C13 C23 112.24(18) . .
C14 C13 C23 111.64(17) . .
C12 C13 C20 108.89(17) . .
C14 C13 C20 112.34(17) . .
C23 C13 C20 99.00(17) . .
N3 C14 C15 120.32(19) . .
N3 C14 C13 119.14(18) . .
C15 C14 C13 120.51(19) . .
C14 C15 C16 120.1(2) . .
C14 C15 H15 119.9 . .
C16 C15 H15 119.9 . .
C17 C16 C15 119.1(2) . .
C17 C16 H16 120.4 . .
C15 C16 H16 120.4 . .
C16 C17 C18 118.8(2) . .
C16 C17 H17 120.6 . .
C18 C17 H17 120.6 . .
N3 C18 C17 122.22(19) . .
N3 C18 C19 119.26(18) . .
C17 C18 C19 118.47(19) . .
C18 C19 P2 112.32(14) . .
C18 C19 H19A 109.1 . .
P2 C19 H19A 109.1 . .
C18 C19 H19B 109.1 . .
P2 C19 H19B 109.1 . .
H19A C19 H19B 107.9 . .
C21 C20 C13 104.33(18) . .
C21 C20 H20A 110.9 . .
C13 C20 H20A 110.9 . .
C21 C20 H20B 110.9 . .
C13 C20 H20B 110.9 . .
H20A C20 H20B 108.9 . .
C20 C21 C22 107.34(19) . .
C20 C21 H21A 110.2 . .
C22 C21 H21A 110.2 . .
C20 C21 H21B 110.2 . .
C22 C21 H21B 110.2 . .
H21A C21 H21B 108.5 . .
C21 C22 C23 104.50(19) . .
C21 C22 H22A 110.9 . .
C23 C22 H22A 110.9 . .
C21 C22 H22B 110.9 . .
C23 C22 H22B 110.9 . .
H22A C22 H22B 108.9 . .
C22 C23 C13 106.19(18) . .
C22 C23 H23A 110.5 . .
C13 C23 H23A 110.5 . .
C22 C23 H23B 110.5 . .
C13 C23 H23B 110.5 . .
H23A C23 H23B 108.7 . .
C26 C24 C27 108.22(18) . .
C26 C24 C25 109.56(18) . .
C27 C24 C25 107.16(18) . .
C26 C24 P2 110.43(15) . .
C27 C24 P2 107.89(14) . .
C25 C24 P2 113.40(15) . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C24 C26 H26A 109.5 . .
C24 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C24 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C24 C27 H27A 109.5 . .
C24 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C24 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C31 C28 C29 109.83(19) . .
C31 C28 C30 106.88(19) . .
C29 C28 C30 107.43(19) . .
C31 C28 P2 113.89(16) . .
C29 C28 P2 110.73(16) . .
C30 C28 P2 107.79(15) . .
C28 C29 H29A 109.5 . .
C28 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C28 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C28 C30 H30A 109.5 . .
C28 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
C28 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C28 C31 H31A 109.5 . .
C28 C31 H31B 109.5 . .
H31A C31 H31B 109.5 . .
C28 C31 H31C 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
C34 C32 C33 119.5(3) . 3_777
C34 C32 H32 120.2 . .
C33 C32 H32 120.2 3_777 .
C34 C33 C32 120.3(3) . 3_777
C34 C33 H33 119.9 . .
C32 C33 H33 119.9 3_777 .
C32 C34 C33 120.2(3) . .
C32 C34 H34 119.9 . .
C33 C34 H34 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ru1 C6 1.846(3) .
Ru1 N4 2.1752(17) .
Ru1 N3 2.1772(17) .
Ru1 P2 2.2754(6) .
Ru1 Cl5 2.5612(6) .
Ru1 H1 1.74(2) .
P2 C19 1.826(2) .
P2 C28 1.885(2) .
P2 C24 1.889(2) .
N3 C18 1.356(3) .
N3 C14 1.360(3) .
N4 C8 1.346(3) .
N4 C12 1.357(3) .
C6 O7 1.105(3) .
C8 C9 1.375(3) .
C8 H8 0.9500 .
C9 C10 1.377(3) .
C9 H9 0.9500 .
C10 C11 1.384(3) .
C10 H10 0.9500 .
C11 C12 1.396(3) .
C11 H11 0.9500 .
C12 C13 1.530(3) .
C13 C14 1.533(3) .
C13 C23 1.551(3) .
C13 C20 1.561(3) .
C14 C15 1.393(3) .
C15 C16 1.389(3) .
C15 H15 0.9500 .
C16 C17 1.377(3) .
C16 H16 0.9500 .
C17 C18 1.392(3) .
C17 H17 0.9500 .
C18 C19 1.500(3) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.526(3) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C22 1.527(3) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C23 1.533(3) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C26 1.530(3) .
C24 C27 1.536(3) .
C24 C25 1.540(3) .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
C28 C31 1.534(3) .
C28 C29 1.540(3) .
C28 C30 1.539(3) .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
C31 H31A 0.9800 .
C31 H31B 0.9800 .
C31 H31C 0.9800 .
C32 C34 1.377(4) .
C32 C33 1.376(4) 3_777
C32 H32 0.9500 .
C33 C34 1.373(4) .
C33 C32 1.376(4) 3_777
C33 H33 0.9500 .
C34 H34 0.9500 .
