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#$Date: 2019-11-24 13:13:38 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237985 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/91/4089103.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_4089103
loop_
_publ_author_name
'Paul, Daniel'
'Beiring, Bernhard'
'Plois, Markus'
'Ortega, Nuria'
'Kock, Slawomir'
'Schlüns, Danny'
'Neugebauer, Johannes'
'Wolf, Robert'
'Glorius, Frank'
_publ_section_title
;
 A Cyclometalated Ruthenium-NHC Precatalyst for the Asymmetric
 Hydrogenation of (Hetero)arenes and Its Activation Pathway
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              3641
_journal_paper_doi               10.1021/acs.organomet.6b00702
_journal_volume                  35
_journal_year                    2016
_chemical_formula_sum            'C38 H62 N4 Ru'
_chemical_formula_weight         675.99
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_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                 100.9810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2090(4)
_cell_length_b                   18.2754(9)
_cell_length_c                   21.1889(9)
_cell_measurement_reflns_used    9152
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      29.67
_cell_measurement_theta_min      2.23
_cell_volume                     3500.8(3)
_computing_cell_refinement       'APEX2(Bruker AXS, 2007)'
_computing_data_collection       'APEX2(Bruker AXS, 2007)'
_computing_data_reduction        'SAINT,SADABS (Bruker AXS, 2007 )'
_computing_molecular_graphics
;
ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565
;
_computing_structure_refinement
;
SHELXL-97, G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122
;
_computing_structure_solution
;
SHELXS-97 , G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122
;
_diffrn_ambient_temperature      153(1)
_diffrn_detector_area_resol_mean 80
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19964
_diffrn_reflns_theta_full        29.72
_diffrn_reflns_theta_max         29.72
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_T_max  0.9649
_exptl_absorpt_correction_T_min  0.9145
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0240
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0318P)²+1.6885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0597
_refine_ls_wR_factor_ref         0.0613
_reflns_number_gt                4574
_reflns_number_total             4973
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om6b00702_si_003.cif
_cod_data_source_block           mp010411
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4089103
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 0.5000 0.600017(7) 0.7500 0.01500(5) Uani 1 2 d S
N1 N 0.66097(12) 0.45428(6) 0.71841(5) 0.0197(2) Uani 1 1 d .
C1 C 0.65752(13) 0.51647(7) 0.75539(6) 0.0172(2) Uani 1 1 d .
N2 N 0.78339(12) 0.50858(6) 0.80201(6) 0.0201(2) Uani 1 1 d .
C2 C 0.78231(15) 0.41084(8) 0.74258(7) 0.0253(3) Uani 1 1 d .
C3 C 0.85832(15) 0.44445(8) 0.79461(7) 0.0254(3) Uani 1 1 d .
C4 C 0.55829(14) 0.43416(7) 0.65845(6) 0.0200(2) Uani 1 1 d .
C5 C 0.48193(15) 0.36042(7) 0.66427(7) 0.0228(3) Uani 1 1 d .
H5A H 0.5575 0.3215 0.6743 0.027 Uiso 1 1 calc R
H5B H 0.4265 0.3627 0.6999 0.027 Uiso 1 1 calc R
C6 C 0.37552(15) 0.34179(8) 0.60157(7) 0.0256(3) Uani 1 1 d .
H6A H 0.3294 0.2936 0.6060 0.031 Uiso 1 1 calc R
H6B H 0.2958 0.3789 0.5933 0.031 Uiso 1 1 calc R
C7 C 0.45561(17) 0.33965(8) 0.54477(7) 0.0296(3) Uani 1 1 d .
H7A H 0.5292 0.2995 0.5509 0.036 Uiso 1 1 calc R
H7B H 0.3835 0.3301 0.5046 0.036 Uiso 1 1 calc R
C8 C 0.53331(18) 0.41234(8) 0.53926(7) 0.0298(3) Uani 1 1 d .
H8A H 0.4584 0.4515 0.5287 0.036 Uiso 1 1 calc R
H8B H 0.5892 0.4094 0.5038 0.036 Uiso 1 1 calc R
C9 C 0.63962(16) 0.43179(8) 0.60177(7) 0.0256(3) Uani 1 1 d .
H9A H 0.6851 0.4801 0.5971 0.031 Uiso 1 1 calc R
H9B H 0.7198 0.3949 0.6104 0.031 Uiso 1 1 calc R
C10 C 0.84126(14) 0.56338(7) 0.85117(6) 0.0194(2) Uani 1 1 d .
C11 C 0.83828(15) 0.53647(8) 0.91894(7) 0.0235(3) Uani 1 1 d .
H11A H 0.9012 0.4924 0.9283 0.028 Uiso 1 1 calc R
H11B H 0.7359 0.5229 0.9222 0.028 Uiso 1 1 calc R
C12 C 0.89484(16) 0.59648(8) 0.96806(7) 0.0273(3) Uani 1 1 d .
H12A H 0.8267 0.6388 0.9609 0.033 Uiso 1 1 calc R
H12B H 0.8960 0.5777 1.0120 0.033 Uiso 1 1 calc R
C13 C 1.05605(16) 0.64575(8) 0.89432(7) 0.0276(3) Uani 1 1 d .
H13A H 1.1593 0.6578 0.8913 0.033 Uiso 1 1 calc R
H13B H 0.9957 0.6905 0.8841 0.033 Uiso 1 1 calc R
C14 C 1.05063(16) 0.62141(9) 0.96264(7) 0.0287(3) Uani 1 1 d .
H14A H 1.0811 0.6625 0.9927 0.034 Uiso 1 1 calc R
H14B H 1.1211 0.5806 0.9750 0.034 Uiso 1 1 calc R
C15 C 0.99808(15) 0.58623(8) 0.84548(7) 0.0255(3) Uani 1 1 d .
H15A H 1.0644 0.5432 0.8529 0.031 Uiso 1 1 calc R
H15B H 0.9978 0.6047 0.8015 0.031 Uiso 1 1 calc R
C16 C 0.31546(14) 0.67441(7) 0.76580(7) 0.0217(3) Uani 1 1 d .
C17 C 0.43690(14) 0.67694(7) 0.81798(7) 0.0208(2) Uani 1 1 d .
C18 C 0.47716(15) 0.61121(7) 0.85262(7) 0.0216(3) Uani 1 1 d .
C19 C 0.51920(17) 0.74706(8) 0.83873(8) 0.0281(3) Uani 1 1 d .
H19A H 0.5122 0.7799 0.8017 0.042 Uiso 1 1 calc R
H19B H 0.6234 0.7360 0.8558 0.042 Uiso 1 1 calc R
H19C H 0.4754 0.7708 0.8721 0.042 Uiso 1 1 calc R
H10 H 0.7763(17) 0.6051(8) 0.8409(8) 0.015(4) Uiso 1 1 d .
H4 H 0.4860(17) 0.4708(8) 0.6518(7) 0.018(4) Uiso 1 1 d .
H18 H 0.3984(17) 0.5800(8) 0.8603(7) 0.014(3) Uiso 1 1 d .
H19 H 0.560(2) 0.6151(9) 0.8890(8) 0.025(4) Uiso 1 1 d .
H17 H 0.2880(18) 0.7197(9) 0.7409(8) 0.026(4) Uiso 1 1 d .
H2 H 0.9459(19) 0.4310(9) 0.8234(8) 0.025(4) Uiso 1 1 d .
H1 H 0.800(2) 0.3681(11) 0.7233(9) 0.038(5) Uiso 1 1 d .
H16 H 0.2330(18) 0.6444(9) 0.7693(8) 0.024(4) Uiso 1 1 d .
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'
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
C1 Ru1 C1 86.38(7) 2_656 .
C1 Ru1 C17 103.79(5) 2_656 .
C1 Ru1 C17 134.95(5) . .
C1 Ru1 C17 134.95(5) 2_656 2_656
C1 Ru1 C17 103.79(5) . 2_656
C17 Ru1 C17 99.23(7) . 2_656
C1 Ru1 C18 85.82(5) 2_656 .
C1 Ru1 C18 101.91(5) . .
C17 Ru1 C18 37.59(5) . .
C17 Ru1 C18 132.36(5) 2_656 .
C1 Ru1 C18 101.91(5) 2_656 2_656
C1 Ru1 C18 85.82(5) . 2_656
C17 Ru1 C18 132.36(5) . 2_656
C17 Ru1 C18 37.59(5) 2_656 2_656
C18 Ru1 C18 169.49(7) . 2_656
C1 Ru1 C16 85.05(5) 2_656 .
C1 Ru1 C16 165.28(5) . .
C17 Ru1 C16 37.30(5) . .
C17 Ru1 C16 90.72(5) 2_656 .
C18 Ru1 C16 65.55(5) . .
C18 Ru1 C16 107.65(5) 2_656 .
C1 Ru1 C16 165.28(5) 2_656 2_656
C1 Ru1 C16 85.05(5) . 2_656
C17 Ru1 C16 90.72(5) . 2_656
C17 Ru1 C16 37.30(5) 2_656 2_656
C18 Ru1 C16 107.65(5) . 2_656
C18 Ru1 C16 65.55(5) 2_656 2_656
C16 Ru1 C16 105.67(7) . 2_656
C1 N1 C2 111.39(11) . .
C1 N1 C4 127.64(11) . .
C2 N1 C4 120.89(11) . .
N2 C1 N1 102.28(10) . .
N2 C1 Ru1 126.44(9) . .
N1 C1 Ru1 131.15(9) . .
C1 N2 C3 112.11(11) . .
C1 N2 C10 125.30(11) . .
C3 N2 C10 122.41(11) . .
C3 C2 N1 107.45(12) . .
C2 C3 N2 106.76(12) . .
N1 C4 C9 110.64(11) . .
N1 C4 C5 112.14(11) . .
C9 C4 C5 109.74(11) . .
C6 C5 C4 110.64(11) . .
C7 C6 C5 111.35(12) . .
C8 C7 C6 110.02(12) . .
C7 C8 C9 111.61(12) . .
C8 C9 C4 110.92(12) . .
N2 C10 C11 112.27(11) . .
N2 C10 C15 110.51(11) . .
C11 C10 C15 110.44(11) . .
C10 C11 C12 110.14(11) . .
C14 C12 C11 111.35(12) . .
C14 C13 C15 111.45(12) . .
C13 C14 C12 111.04(12) . .
C13 C15 C10 110.77(11) . .
C17 C16 Ru1 68.25(7) . .
C16 C17 C18 117.76(12) . .
C16 C17 C19 122.19(12) . .
C18 C17 C19 120.01(12) . .
C16 C17 Ru1 74.45(8) . .
C18 C17 Ru1 73.64(8) . .
C19 C17 Ru1 124.04(9) . .
C17 C18 Ru1 68.78(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ru1 C1 2.0941(12) 2_656
Ru1 C1 2.0942(12) .
Ru1 C17 2.1698(13) .
Ru1 C17 2.1698(13) 2_656
Ru1 C18 2.2334(14) .
Ru1 C18 2.2334(14) 2_656
Ru1 C16 2.2506(13) .
Ru1 C16 2.2506(13) 2_656
N1 C1 1.3843(16) .
N1 C2 1.3868(17) .
N1 C4 1.4784(17) .
C1 N2 1.3798(16) .
N2 C3 1.3841(17) .
N2 C10 1.4699(17) .
C2 C3 1.337(2) .
C4 C9 1.5323(18) .
C4 C5 1.5359(19) .
C5 C6 1.5315(19) .
C6 C7 1.527(2) .
C7 C8 1.524(2) .
C8 C9 1.531(2) .
C10 C11 1.5230(19) .
C10 C15 1.5300(18) .
C11 C12 1.533(2) .
C12 C14 1.530(2) .
C13 C14 1.524(2) .
C13 C15 1.526(2) .
C16 C17 1.4157(19) .
C17 C18 1.4197(19) .
C17 C19 1.5109(19) .
