#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:09:00 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180170 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/66/7106683.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_7106683
loop_
_publ_author_name
'Yunshan Sun'
'Christian Koehler'
'Runyu Tan'
'Vincent T. Annibale'
'Datong Song'
_publ_section_title
;
 Ester hydrogenation catalyzed by Ru-CNN pincer complexes
;
_journal_name_full               Chem.Commun.
_journal_page_first              8349
_journal_paper_doi               10.1039/c1cc12601f
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C27 H37 Br N4 O Ru'
_chemical_formula_weight         614.59
_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                 109.140(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9037(5)
_cell_length_b                   16.1438(7)
_cell_length_c                   14.7255(7)
_cell_measurement_reflns_used    54156
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      36.97
_cell_measurement_theta_min      1.92
_cell_volume                     2673.4(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0666
_diffrn_reflns_av_sigmaI/netI    0.0750
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            54156
_diffrn_reflns_theta_full        36.97
_diffrn_reflns_theta_max         36.97
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    2.107
_exptl_absorpt_correction_T_max  0.7568
_exptl_absorpt_correction_T_min  0.6779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.846
_refine_diff_density_min         -1.258
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         13497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0460
_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)+(0.0441P)²+0.2867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.1065
_reflns_number_gt                8556
_reflns_number_total             13497
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc12601f.txt
_cod_data_source_block           2a
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7106683
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.561657(14) 0.178573(10) 0.278385(12) 0.01727(4) Uani 1 1 d . . .
Br1 Br 0.60526(2) 0.235750(18) 0.121748(19) 0.03602(7) Uani 1 1 d . . .
O1 O 0.63218(16) 0.33501(12) 0.38890(15) 0.0390(5) Uani 1 1 d . . .
N1 N 0.73729(15) 0.11271(11) 0.34113(13) 0.0210(3) Uani 1 1 d . . .
N2 N 0.52559(15) 0.06181(11) 0.20668(13) 0.0212(3) Uani 1 1 d . . .
N3 N 0.31492(15) 0.16586(11) 0.14463(13) 0.0215(4) Uani 1 1 d . . .
N4 N 0.31183(14) 0.24637(11) 0.25971(12) 0.0173(3) Uani 1 1 d . . .
C1 C 0.8832(2) 0.19947(17) 0.2928(2) 0.0361(6) Uani 1 1 d . . .
H1A H 0.9363 0.1986 0.2541 0.054 Uiso 1 1 calc R . .
H1B H 0.9298 0.2097 0.3603 0.054 Uiso 1 1 calc R . .
H1C H 0.8242 0.2436 0.2696 0.054 Uiso 1 1 calc R . .
C2 C 0.82056(19) 0.11707(15) 0.28426(18) 0.0272(5) Uani 1 1 d . . .
H2A H 0.7754 0.1066 0.2158 0.033 Uiso 1 1 calc R . .
H2B H 0.8809 0.0728 0.3064 0.033 Uiso 1 1 calc R . .
C3 C 0.9094(2) 0.08965(16) 0.49754(19) 0.0342(5) Uani 1 1 d . . .
H3A H 0.9423 0.1107 0.5634 0.051 Uiso 1 1 calc R . .
H3B H 0.9684 0.0959 0.4647 0.051 Uiso 1 1 calc R . .
H3C H 0.8892 0.0309 0.4992 0.051 Uiso 1 1 calc R . .
C4 C 0.79772(19) 0.13844(15) 0.44362(16) 0.0264(5) Uani 1 1 d . . .
H4A H 0.7401 0.1330 0.4788 0.032 Uiso 1 1 calc R . .
H4B H 0.8192 0.1978 0.4444 0.032 Uiso 1 1 calc R . .
C5 C 0.6975(2) 0.02493(14) 0.34050(18) 0.0284(5) Uani 1 1 d . . .
H5A H 0.6631 0.0169 0.3926 0.034 Uiso 1 1 calc R . .
H5B H 0.7670 -0.0123 0.3531 0.034 Uiso 1 1 calc R . .
C6 C 0.6066(2) 0.00235(14) 0.24614(18) 0.0257(4) Uani 1 1 d . . .
C7 C 0.6020(2) -0.07487(15) 0.2040(2) 0.0354(6) Uani 1 1 d . . .
H7A H 0.6615 -0.1152 0.2319 0.042 Uiso 1 1 calc R . .
C8 C 0.5093(2) -0.09237(16) 0.1204(2) 0.0362(6) Uani 1 1 d . . .
H8A H 0.5030 -0.1454 0.0911 0.043 Uiso 1 1 calc R . .
C9 C 0.4264(2) -0.03168(16) 0.08058(19) 0.0311(5) Uani 1 1 d . . .
H9A H 0.3622 -0.0425 0.0233 0.037 Uiso 1 1 calc R . .
C10 C 0.43704(19) 0.04545(15) 0.12470(16) 0.0246(4) Uani 1 1 d . . .
C11 C 0.3548(2) 0.11540(15) 0.07842(16) 0.0265(5) Uani 1 1 d . . .
H11A H 0.3957 0.1519 0.0452 0.032 Uiso 1 1 calc R . .
H11B H 0.2840 0.0920 0.0290 0.032 Uiso 1 1 calc R . .
C12 C 0.19651(19) 0.18508(14) 0.12906(16) 0.0239(4) Uani 1 1 d . . .
H12A H 0.1299 0.1661 0.0776 0.029 Uiso 1 1 calc R . .
C13 C 0.19414(18) 0.23555(14) 0.20059(16) 0.0216(4) Uani 1 1 d . . .
H13A H 0.1255 0.2594 0.2094 0.026 Uiso 1 1 calc R . .
C14 C 0.38864(17) 0.20351(13) 0.22540(14) 0.0179(4) Uani 1 1 d . . .
C15 C 0.34170(17) 0.29780(13) 0.34497(15) 0.0180(4) Uani 1 1 d . . .
C16 C 0.35218(17) 0.26028(14) 0.43288(15) 0.0203(4) Uani 1 1 d . . .
C17 C 0.37085(19) 0.31217(15) 0.51246(16) 0.0259(5) Uani 1 1 d . . .
H17A H 0.3765 0.2888 0.5730 0.031 Uiso 1 1 calc R . .
C18 C 0.3813(2) 0.39721(15) 0.50455(17) 0.0277(5) Uani 1 1 d . . .
H18A H 0.3942 0.4315 0.5595 0.033 Uiso 1 1 calc R . .
C19 C 0.37305(19) 0.43212(14) 0.41697(17) 0.0256(4) Uani 1 1 d . . .
H19A H 0.3819 0.4903 0.4127 0.031 Uiso 1 1 calc R . .
C20 C 0.35192(18) 0.38352(14) 0.33474(15) 0.0211(4) Uani 1 1 d . . .
C21 C 0.34008(19) 0.16732(14) 0.44266(16) 0.0230(4) Uani 1 1 d . . .
H21A H 0.3484 0.1405 0.3840 0.028 Uiso 1 1 calc R . .
C22 C 0.2169(2) 0.14598(17) 0.4469(2) 0.0332(5) Uani 1 1 d . . .
H22A H 0.1559 0.1689 0.3903 0.050 Uiso 1 1 calc R . .
H22B H 0.2076 0.1697 0.5053 0.050 Uiso 1 1 calc R . .
H22C H 0.2080 0.0857 0.4477 0.050 Uiso 1 1 calc R . .
C23 C 0.4375(2) 0.13214(17) 0.53035(19) 0.0360(6) Uani 1 1 d . . .
H23A H 0.5157 0.1464 0.5264 0.054 Uiso 1 1 calc R . .
H23B H 0.4296 0.0718 0.5316 0.054 Uiso 1 1 calc R . .
H23C H 0.4293 0.1558 0.5892 0.054 Uiso 1 1 calc R . .
C24 C 0.3378(2) 0.42300(14) 0.23838(17) 0.0261(4) Uani 1 1 d . . .
H24A H 0.3419 0.3782 0.1927 0.031 Uiso 1 1 calc R . .
C25 C 0.2161(2) 0.46516(18) 0.1983(2) 0.0380(6) Uani 1 1 d . . .
H25A H 0.1533 0.4248 0.1945 0.057 Uiso 1 1 calc R . .
H25B H 0.2059 0.4869 0.1339 0.057 Uiso 1 1 calc R . .
H25C H 0.2113 0.5108 0.2407 0.057 Uiso 1 1 calc R . .
C26 C 0.4369(2) 0.48542(17) 0.2447(2) 0.0357(6) Uani 1 1 d . . .
H26A H 0.5143 0.4579 0.2704 0.053 Uiso 1 1 calc R . .
H26B H 0.4326 0.5311 0.2873 0.053 Uiso 1 1 calc R . .
H26C H 0.4272 0.5072 0.1805 0.053 Uiso 1 1 calc R . .
C27 C 0.60186(19) 0.27532(15) 0.34607(17) 0.0258(4) Uani 1 1 d . . .
H1 H 0.540(3) 0.1348(18) 0.372(2) 0.043(8) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
_geom_angle_publ_flag
C27 Ru1 C14 95.34(9) . . ?
C27 Ru1 N2 175.93(8) . . ?
C14 Ru1 N2 88.29(8) . . ?
C27 Ru1 N1 97.90(8) . . ?
C14 Ru1 N1 163.17(8) . . ?
N2 Ru1 N1 78.20(7) . . ?
C27 Ru1 Br1 94.86(8) . . ?
C14 Ru1 Br1 93.46(6) . . ?
N2 Ru1 Br1 86.73(5) . . ?
N1 Ru1 Br1 95.71(5) . . ?
C27 Ru1 H1 89.7(10) . . ?
C14 Ru1 H1 89.2(10) . . ?
N2 Ru1 H1 88.6(10) . . ?
N1 Ru1 H1 80.6(10) . . ?
Br1 Ru1 H1 174.5(10) . . ?
C5 N1 C2 107.98(18) . . ?
C5 N1 C4 108.37(18) . . ?
C2 N1 C4 111.28(17) . . ?
C5 N1 Ru1 101.25(12) . . ?
C2 N1 Ru1 116.38(14) . . ?
C4 N1 Ru1 110.82(13) . . ?
C10 N2 C6 119.1(2) . . ?
C10 N2 Ru1 126.13(15) . . ?
C6 N2 Ru1 114.57(15) . . ?
C14 N3 C12 111.83(17) . . ?
C14 N3 C11 124.81(17) . . ?
C12 N3 C11 123.25(18) . . ?
C14 N4 C13 111.20(17) . . ?
C14 N4 C15 127.28(16) . . ?
C13 N4 C15 121.52(16) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 113.3(2) . . ?
N1 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
N1 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C3 115.4(2) . . ?
N1 C4 H4A 108.4 . . ?
C3 C4 H4A 108.4 . . ?
N1 C4 H4B 108.4 . . ?
C3 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
N1 C5 C6 111.56(19) . . ?
N1 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
N1 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
N2 C6 C7 122.0(2) . . ?
N2 C6 C5 115.0(2) . . ?
C7 C6 C5 123.0(2) . . ?
C6 C7 C8 118.9(2) . . ?
C6 C7 H7A 120.5 . . ?
C8 C7 H7A 120.5 . . ?
C9 C8 C7 118.9(2) . . ?
C9 C8 H8A 120.5 . . ?
C7 C8 H8A 120.5 . . ?
C8 C9 C10 119.6(2) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
N2 C10 C9 121.4(2) . . ?
N2 C10 C11 117.5(2) . . ?
C9 C10 C11 121.0(2) . . ?
N3 C11 C10 114.91(19) . . ?
N3 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
N3 C11 H11B 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 N3 106.76(19) . . ?
C13 C12 H12A 126.6 . . ?
N3 C12 H12A 126.6 . . ?
C12 C13 N4 106.91(18) . . ?
C12 C13 H13A 126.5 . . ?
N4 C13 H13A 126.5 . . ?
N3 C14 N4 103.29(16) . . ?
N3 C14 Ru1 122.53(14) . . ?
N4 C14 Ru1 133.51(15) . . ?
C16 C15 C20 122.89(19) . . ?
C16 C15 N4 118.45(19) . . ?
C20 C15 N4 118.55(18) . . ?
C15 C16 C17 117.3(2) . . ?
C15 C16 C21 122.25(19) . . ?
C17 C16 C21 120.4(2) . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H17A 119.4 . . ?
C16 C17 H17A 119.4 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C18 C19 C20 121.2(2) . . ?
C18 C19 H19A 119.4 . . ?
C20 C19 H19A 119.4 . . ?
C19 C20 C15 117.3(2) . . ?
C19 C20 C24 120.7(2) . . ?
C15 C20 C24 121.98(19) . . ?
C16 C21 C22 110.42(19) . . ?
C16 C21 C23 112.13(19) . . ?
C22 C21 C23 110.7(2) . . ?
C16 C21 H21A 107.8 . . ?
C22 C21 H21A 107.8 . . ?
C23 C21 H21A 107.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 C26 111.92(19) . . ?
C20 C24 C25 110.42(19) . . ?
C26 C24 C25 110.1(2) . . ?
C20 C24 H24A 108.1 . . ?
C26 C24 H24A 108.1 . . ?
C25 C24 H24A 108.1 . . ?
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 . . ?
O1 C27 Ru1 176.9(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 C27 1.830(2) . ?
Ru1 C14 1.9896(19) . ?
Ru1 N2 2.1343(18) . ?
Ru1 N1 2.2557(17) . ?
Ru1 Br1 2.6883(3) . ?
Ru1 H1 1.65(3) . ?
O1 C27 1.143(3) . ?
N1 C5 1.493(3) . ?
N1 C2 1.494(3) . ?
N1 C4 1.502(3) . ?
N2 C10 1.343(3) . ?
N2 C6 1.350(3) . ?
N3 C14 1.367(3) . ?
N3 C12 1.387(3) . ?
N3 C11 1.464(3) . ?
N4 C14 1.369(2) . ?
N4 C13 1.397(3) . ?
N4 C15 1.449(3) . ?
C1 C2 1.510(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.525(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.499(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.386(3) . ?
C7 C8 1.386(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.378(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.391(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.504(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.339(3) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C15 C16 1.397(3) . ?
C15 C20 1.402(3) . ?
C16 C17 1.398(3) . ?
C16 C21 1.519(3) . ?
C17 C18 1.387(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.381(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.395(3) . ?
C19 H19A 0.9500 . ?
C20 C24 1.514(3) . ?
C21 C22 1.527(3) . ?
C21 C23 1.534(3) . ?
C21 H21A 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C26 1.531(3) . ?
C24 C25 1.533(3) . ?
C24 H24A 1.0000 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
