#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/59/4085993.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_4085993
loop_
_publ_author_name
'Dub, Pavel A.'
'Scott, Brian L.'
'Gordon, John C.'
_publ_section_title
;
 Air-Stable NNS (ENENES) Ligands and Their Well-Defined Ruthenium and
 Iridium Complexes for Molecular Catalysis
;
_journal_issue                   18
_journal_name_full               Organometallics
_journal_page_first              4464
_journal_paper_doi               10.1021/acs.organomet.5b00432
_journal_volume                  34
_journal_year                    2015
_chemical_formula_sum            'C32 H37 Cl2 N2 P Ru S'
_chemical_formula_weight         684.64
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 100.8621(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3957(9)
_cell_length_b                   10.2189(7)
_cell_length_c                   24.5583(17)
_cell_measurement_temperature    100(1)
_cell_volume                     3055.1(4)
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker D8 Quest with CMOS detector'
_diffrn_measurement_method       'ω 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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            70925
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         35.39
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  0.8510
_exptl_absorpt_correction_T_min  0.7315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.777
_refine_diff_density_min         -1.683
_refine_diff_density_rms         0.253
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.437
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         13131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.437
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0239
_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)+(0.0416P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                11680
_reflns_number_total             13131
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00432_si_002.cif
_cod_data_source_block           dq0035
_cod_depositor_comments
'Adding full bibliography for 4085982--4085994.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4085993
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.151407(6) 0.681324(8) 0.106602(3) 0.00859(3) Uani 1 1 d .
Cl1 Cl 0.08959(2) 0.83291(2) 0.170507(11) 0.01350(5) Uani 1 1 d .
Cl2 Cl 0.17150(2) 0.51306(2) 0.038143(10) 0.01238(5) Uani 1 1 d .
S1 S 0.09332(2) 0.83822(2) 0.039349(11) 0.00996(5) Uani 1 1 d .
P1 P 0.32828(2) 0.76577(3) 0.131149(11) 0.00912(5) Uani 1 1 d .
N1 N -0.01544(7) 0.61701(9) 0.08542(4) 0.01218(15) Uani 1 1 d .
H1 H -0.0189 0.5598 0.0568 0.015 Uiso 1 1 calc R
N2 N 0.15844(7) 0.52662(9) 0.16960(4) 0.01224(16) Uani 1 1 d .
C1 C 0.13651(9) 0.82650(10) -0.02611(5) 0.01190(18) Uani 1 1 d .
C2 C 0.23828(9) 0.77332(11) -0.02925(5) 0.01489(19) Uani 1 1 d .
H2 H 0.2830 0.7398 0.0023 0.018 Uiso 1 1 calc R
C3 C 0.27272(10) 0.77053(12) -0.07976(5) 0.0200(2) Uani 1 1 d .
H3 H 0.3413 0.7361 -0.0818 0.024 Uiso 1 1 calc R
C4 C 0.20563(12) 0.81887(12) -0.12766(6) 0.0222(3) Uani 1 1 d .
H4 H 0.2283 0.8143 -0.1616 0.027 Uiso 1 1 calc R
C5 C 0.10480(11) 0.87378(13) -0.12408(5) 0.0210(2) Uani 1 1 d .
H5 H 0.0601 0.9073 -0.1557 0.025 Uiso 1 1 calc R
C6 C 0.07037(9) 0.87890(11) -0.07348(5) 0.01593(19) Uani 1 1 d .
H6 H 0.0033 0.9172 -0.0711 0.019 Uiso 1 1 calc R
C7 C -0.05137(8) 0.79051(11) 0.01728(5) 0.01307(18) Uani 1 1 d .
H7A H -0.0956 0.8673 0.0054 0.016 Uiso 1 1 calc R
H7B H -0.0585 0.7304 -0.0138 0.016 Uiso 1 1 calc R
C8 C -0.09151(8) 0.72561(11) 0.06516(5) 0.01354(18) Uani 1 1 d .
H8A H -0.0928 0.7884 0.0946 0.016 Uiso 1 1 calc R
H8B H -0.1654 0.6922 0.0530 0.016 Uiso 1 1 calc R
C9 C -0.04164(9) 0.54184(12) 0.13264(5) 0.0166(2) Uani 1 1 d .
H9A H -0.1089 0.4925 0.1212 0.020 Uiso 1 1 calc R
H9B H -0.0513 0.6005 0.1624 0.020 Uiso 1 1 calc R
C10 C 0.05398(9) 0.45004(11) 0.15188(5) 0.0164(2) Uani 1 1 d .
H10A H 0.0395 0.3979 0.1827 0.020 Uiso 1 1 calc R
H10B H 0.0621 0.3911 0.1220 0.020 Uiso 1 1 calc R
C11 C 0.16690(9) 0.56465(11) 0.22940(4) 0.01491(19) Uani 1 1 d .
H11A H 0.0962 0.5938 0.2363 0.018 Uiso 1 1 calc R
H11B H 0.2197 0.6349 0.2391 0.018 Uiso 1 1 calc R
C12 C 0.20506(11) 0.44044(12) 0.26378(5) 0.0207(2) Uani 1 1 d .
H12A H 0.2600 0.4622 0.2961 0.025 Uiso 1 1 calc R
H12B H 0.1435 0.3983 0.2759 0.025 Uiso 1 1 calc R
C13 C 0.25403(11) 0.35034(12) 0.22424(5) 0.0205(2) Uani 1 1 d .
H13A H 0.3278 0.3229 0.2409 0.025 Uiso 1 1 calc R
H13B H 0.2086 0.2734 0.2145 0.025 Uiso 1 1 calc R
C14 C 0.25488(9) 0.43689(11) 0.17325(5) 0.01444(19) Uani 1 1 d .
H14A H 0.3226 0.4866 0.1776 0.017 Uiso 1 1 calc R
H14B H 0.2481 0.3838 0.1400 0.017 Uiso 1 1 calc R
C15 C 0.45131(9) 0.68881(10) 0.11309(4) 0.01074(17) Uani 1 1 d .
C16 C 0.44290(8) 0.57548(10) 0.08099(4) 0.01184(17) Uani 1 1 d .
H16 H 0.3747 0.5366 0.0691 0.014 Uiso 1 1 calc R
C17 C 0.53691(9) 0.51997(11) 0.06663(4) 0.01297(18) Uani 1 1 d .
H17 H 0.5307 0.4438 0.0456 0.016 Uiso 1 1 calc R
C18 C 0.63910(9) 0.57721(11) 0.08344(5) 0.01554(19) Uani 1 1 d .
H18 H 0.7009 0.5411 0.0729 0.019 Uiso 1 1 calc R
C19 C 0.64857(9) 0.68959(11) 0.11643(5) 0.0161(2) Uani 1 1 d .
H19 H 0.7170 0.7280 0.1282 0.019 Uiso 1 1 calc R
C20 C 0.55594(9) 0.74396(11) 0.13158(5) 0.01383(18) Uani 1 1 d .
H20 H 0.5630 0.8176 0.1542 0.017 Uiso 1 1 calc R
C21 C 0.38111(8) 0.78493(10) 0.20633(4) 0.01093(17) Uani 1 1 d .
C22 C 0.44524(9) 0.68528(10) 0.23528(5) 0.01309(18) Uani 1 1 d .
H22 H 0.4636 0.6129 0.2160 0.016 Uiso 1 1 calc R
C23 C 0.48206(9) 0.69232(11) 0.29239(5) 0.01498(19) Uani 1 1 d .
H23 H 0.5242 0.6249 0.3109 0.018 Uiso 1 1 calc R
C24 C 0.45561(10) 0.80045(12) 0.32159(5) 0.0162(2) Uani 1 1 d .
H24 H 0.4807 0.8062 0.3597 0.019 Uiso 1 1 calc R
C25 C 0.39163(9) 0.89984(11) 0.29370(5) 0.0163(2) Uani 1 1 d .
H25 H 0.3739 0.9722 0.3133 0.020 Uiso 1 1 calc R
C26 C 0.35359(9) 0.89222(11) 0.23643(4) 0.01364(18) Uani 1 1 d .
H26 H 0.3098 0.9588 0.2183 0.016 Uiso 1 1 calc R
C27 C 0.33921(9) 0.93306(10) 0.10360(4) 0.01226(17) Uani 1 1 d .
C28 C 0.41537(10) 0.96803(11) 0.07037(5) 0.0178(2) Uani 1 1 d .
H28 H 0.4669 0.9071 0.0635 0.021 Uiso 1 1 calc R
C29 C 0.41455(11) 1.09362(12) 0.04755(5) 0.0221(2) Uani 1 1 d .
H29 H 0.4657 1.1155 0.0258 0.027 Uiso 1 1 calc R
C30 C 0.33804(12) 1.18554(11) 0.05710(6) 0.0220(3) Uani 1 1 d .
H30 H 0.3377 1.2691 0.0420 0.026 Uiso 1 1 calc R
C31 C 0.26211(10) 1.15140(11) 0.08935(5) 0.0185(2) Uani 1 1 d .
H31 H 0.2103 1.2125 0.0957 0.022 Uiso 1 1 calc R
C32 C 0.26210(9) 1.02742(10) 0.11239(5) 0.01448(19) Uani 1 1 d .
H32 H 0.2103 1.0066 0.1339 0.017 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'
S S 0.1246 0.1234 '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'
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
N1 Ru1 N2 81.88(3)
N1 Ru1 S1 83.28(3)
N2 Ru1 S1 164.44(2)
N1 Ru1 P1 175.92(3)
N2 Ru1 P1 99.99(2)
S1 Ru1 P1 94.538(10)
N1 Ru1 Cl1 86.83(3)
N2 Ru1 Cl1 88.82(2)
S1 Ru1 Cl1 85.744(11)
P1 Ru1 Cl1 89.580(10)
N1 Ru1 Cl2 80.57(3)
N2 Ru1 Cl2 89.00(3)
S1 Ru1 Cl2 93.131(10)
P1 Ru1 Cl2 103.023(9)
Cl1 Ru1 Cl2 167.397(9)
C1 S1 C7 99.07(5)
C1 S1 Ru1 119.21(4)
C7 S1 Ru1 100.45(4)
C15 P1 C21 97.59(5)
C15 P1 C27 100.67(5)
C21 P1 C27 103.32(5)
C15 P1 Ru1 124.15(3)
C21 P1 Ru1 115.90(3)
C27 P1 Ru1 112.19(3)
C9 N1 C8 115.68(8)
C9 N1 Ru1 108.33(6)
C8 N1 Ru1 112.14(7)
C14 N2 C11 101.07(8)
C14 N2 C10 109.44(8)
C11 N2 C10 108.34(9)
C14 N2 Ru1 114.05(7)
C11 N2 Ru1 119.13(7)
C10 N2 Ru1 104.60(6)
C2 C1 C6 120.02(10)
C2 C1 S1 120.26(8)
C6 C1 S1 119.58(8)
C3 C2 C1 119.59(10)
C2 C3 C4 120.77(11)
C5 C4 C3 119.35(11)
C4 C5 C6 120.27(11)
C5 C6 C1 119.96(10)
C8 C7 S1 109.42(7)
N1 C8 C7 107.93(8)
N1 C9 C10 106.97(9)
N2 C10 C9 110.36(9)
N2 C11 C12 106.18(9)
C13 C12 C11 105.18(9)
C14 C13 C12 103.51(9)
N2 C14 C13 105.90(9)
C16 C15 C20 118.75(10)
C16 C15 P1 120.91(8)
C20 C15 P1 120.34(8)
C15 C16 C17 120.15(10)
C18 C17 C16 120.77(10)
C17 C18 C19 119.46(10)
C20 C19 C18 120.06(10)
C19 C20 C15 120.75(10)
C26 C21 C22 118.22(10)
C26 C21 P1 122.30(8)
C22 C21 P1 119.35(8)
C23 C22 C21 121.38(10)
C24 C23 C22 119.75(10)
C25 C24 C23 119.73(10)
C24 C25 C26 120.57(10)
C25 C26 C21 120.33(10)
C32 C27 C28 117.80(10)
C32 C27 P1 118.63(8)
C28 C27 P1 123.37(8)
C29 C28 C27 120.70(11)
C30 C29 C28 120.49(12)
C31 C30 C29 119.13(11)
C30 C31 C32 121.05(11)
C31 C32 C27 120.83(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ru1 N1 2.1388(9)
Ru1 N2 2.2022(9)
Ru1 S1 2.3170(3)
Ru1 P1 2.3274(3)
Ru1 Cl1 2.4296(3)
Ru1 Cl2 2.4501(3)
S1 C1 1.7916(11)
S1 C7 1.8389(11)
P1 C15 1.8428(11)
P1 C21 1.8494(10)
P1 C27 1.8529(11)
N1 C9 1.4771(14)
N1 C8 1.4804(14)
N2 C14 1.4958(14)
N2 C11 1.5035(14)
N2 C10 1.5054(15)
C1 C2 1.3890(15)
C1 C6 1.3974(15)
C2 C3 1.3862(16)
C3 C4 1.3967(18)
C4 C5 1.3879(18)
C5 C6 1.3889(16)
C7 C8 1.5134(16)
C9 C10 1.5157(16)
C11 C12 1.5483(16)
C12 C13 1.5431(17)
C13 C14 1.5347(17)
C15 C16 1.3937(14)
C15 C20 1.4086(15)
C16 C17 1.3996(14)
C17 C18 1.3856(15)
C18 C19 1.3975(17)
C19 C20 1.3880(15)
C21 C26 1.4000(15)
C21 C22 1.4005(15)
C22 C23 1.3926(16)
C23 C24 1.3896(16)
C24 C25 1.3874(17)
C25 C26 1.3987(15)
C27 C32 1.4028(15)
C27 C28 1.4054(16)
C28 C29 1.3996(17)
C29 C30 1.3858(19)
C30 C31 1.384(2)
C31 C32 1.3876(16)
