# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'T. Brent Gunnoe'
_publ_contact_author_address     
;

;

_publ_contact_author_email       'brent gunnoe@ncsu.edu'
_publ_contact_author_phone       (919)513-3704
_publ_contact_author_fax         (919)515-8909
loop_
_publ_author_name
_publ_author_address
T.B.Gunnoe
;Department of Chemistry
Box 8204
North Carolina State University
Raleigh, NC 27607
USA
;
L.A.Goj
;Department of Chemistry
Box 8204
North Carolina State University
Raleigh, NC 27607
USA
;
M.Lail
;Department of Chemistry
Box 8204
North Carolina State University
Raleigh, NC 27607
USA
;
K.A.Pittard
;Department of Chemistry
Box 8204
North Carolina State University
Raleigh, NC 27607
USA
;
K.C.Riley
;Department of Chemistry
Box 8204
North Carolina State University
Raleigh, NC 27607
USA
;
J.L.Petersen
;Chemistry Department
West Virginia University
P.O. Box 6045
Morgantown, WV 26506-6045
USA
;

_publ_section_title              
;
Reactions of TpRu(CO)(NCMe)(Ph) with Electron-Rich
Olefins: Examples of Stoichiometric C-S, C-O and C-H Bond Cleavage
;

data_bg454plt
_database_code_depnum_ccdc_archive 'CCDC 286180'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12.50 H16 B Cl N6 O Ru S'
_chemical_formula_weight         445.70

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'
B B 0.0013 0.0007 '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'
S S 0.1246 0.1234 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   7.9135(15)
_cell_length_b                   16.956(3)
_cell_length_c                   12.898(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.377(3)
_cell_angle_gamma                90.00
_cell_volume                     1729.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             892
_exptl_absorpt_coefficient_mu    1.194
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11341
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         27.54
_reflns_number_total             3833
_reflns_number_gt                3118
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0753P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3833
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.002

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 1.06280(3) 0.103598(15) 0.489750(19) 0.03227(13) Uani 1 1 d . . .
S1 S 0.81624(10) 0.02171(5) 0.45859(6) 0.0358(2) Uani 1 1 d . . .
O1 O 1.1781(5) 0.09370(18) 0.2742(2) 0.0620(8) Uani 1 1 d . . .
N1 N 0.9687(3) 0.13692(18) 0.6408(2) 0.0383(6) Uani 1 1 d . . .
N2 N 1.0017(4) 0.21231(19) 0.6750(2) 0.0423(7) Uani 1 1 d . . .
N3 N 1.2823(3) 0.16768(17) 0.5333(2) 0.0394(6) Uani 1 1 d . . .
N4 N 1.2702(4) 0.23820(17) 0.5829(2) 0.0421(7) Uani 1 1 d . . .
N5 N 0.9531(4) 0.21370(17) 0.4462(2) 0.0389(6) Uani 1 1 d . . .
N6 N 0.9897(4) 0.27801(17) 0.5043(3) 0.0441(7) Uani 1 1 d . . .
C1 C 1.1347(5) 0.0933(2) 0.3588(3) 0.0414(8) Uani 1 1 d . . .
C2 C 0.8653(5) 0.1056(2) 0.7078(3) 0.0498(9) Uani 1 1 d . . .
H2 H 0.8231 0.0545 0.7039 0.060 Uiso 1 1 calc R . .
C3 C 0.8282(6) 0.1602(3) 0.7855(3) 0.0607(11) Uani 1 1 d . . .
H3 H 0.7586 0.1529 0.8411 0.073 Uiso 1 1 calc R . .
C4 C 0.9165(5) 0.2261(3) 0.7615(3) 0.0533(10) Uani 1 1 d . . .
H4 H 0.9179 0.2731 0.7988 0.064 Uiso 1 1 calc R . .
C5 C 1.4466(4) 0.1546(3) 0.5211(3) 0.0460(9) Uani 1 1 d . . .
H5 H 1.4907 0.1100 0.4902 0.055 Uiso 1 1 calc R . .
C6 C 1.5427(5) 0.2173(3) 0.5612(3) 0.0542(10) Uani 1 1 d . . .
H6 H 1.6595 0.2234 0.5615 0.065 Uiso 1 1 calc R . .
C7 C 1.4268(5) 0.2676(2) 0.5997(3) 0.0483(9) Uani 1 1 d . . .
H7 H 1.4521 0.3151 0.6327 0.058 Uiso 1 1 calc R . .
C8 C 0.8546(5) 0.2382(3) 0.3657(3) 0.0517(9) Uani 1 1 d . . .
H8 H 0.8110 0.2058 0.3130 0.062 Uiso 1 1 calc R . .
C9 C 0.8266(6) 0.3184(3) 0.3719(4) 0.0653(12) Uani 1 1 d . . .
H9 H 0.7620 0.3496 0.3261 0.078 Uiso 1 1 calc R . .
C10 C 0.9149(5) 0.3420(3) 0.4604(4) 0.0595(11) Uani 1 1 d . . .
H10 H 0.9218 0.3933 0.4858 0.071 Uiso 1 1 calc R . .
C11 C 0.7610(5) 0.0180(3) 0.3190(3) 0.0543(10) Uani 1 1 d . . .
H11A H 0.7872 0.0685 0.2882 0.065 Uiso 1 1 calc R . .
H11B H 0.8302 -0.0217 0.2871 0.065 Uiso 1 1 calc R . .
C12 C 0.5805(6) -0.0004(4) 0.2959(4) 0.0819(16) Uani 1 1 d . . .
H12A H 0.5667 -0.0564 0.2888 0.123 Uiso 1 1 calc R . .
H12B H 0.5436 0.0250 0.2325 0.123 Uiso 1 1 calc R . .
H12C H 0.5142 0.0182 0.3516 0.123 Uiso 1 1 calc R . .
B1 B 1.0952(5) 0.2709(2) 0.6059(3) 0.0447(9) Uani 1 1 d . . .
H1 H 1.1059 0.3224 0.6400 0.054 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ru1 0.03429(17) 0.02477(18) 0.03764(19) -0.00223(9) 0.00013(11) 0.00218(9)
S1 0.0358(4) 0.0284(4) 0.0430(4) -0.0026(3) -0.0024(3) 0.0035(3)
O1 0.082(2) 0.057(2) 0.0483(17) 0.0002(13) 0.0188(16) -0.0019(15)
N1 0.0421(14) 0.0277(15) 0.0451(16) -0.0035(12) 0.0015(12) 0.0037(12)
N2 0.0418(14) 0.0386(17) 0.0467(16) -0.0093(12) 0.0029(12) 0.0023(12)
N3 0.0380(14) 0.0318(16) 0.0483(16) -0.0044(12) -0.0004(12) 0.0003(11)
N4 0.0436(15) 0.0267(15) 0.0553(17) -0.0016(12) -0.0044(13) -0.0057(12)
N5 0.0417(14) 0.0287(15) 0.0459(15) 0.0006(11) -0.0009(12) 0.0045(12)
N6 0.0452(15) 0.0233(15) 0.0635(19) 0.0017(12) -0.0016(13) 0.0011(13)
C1 0.0451(18) 0.0317(19) 0.047(2) 0.0010(14) -0.0003(16) -0.0011(14)
C2 0.054(2) 0.046(2) 0.050(2) -0.0059(16) 0.0093(18) 0.0013(17)
C3 0.066(2) 0.064(3) 0.053(2) -0.005(2) 0.014(2) 0.008(2)
C4 0.058(2) 0.054(3) 0.048(2) -0.0165(18) 0.0059(17) 0.0046(19)
C5 0.0400(17) 0.046(2) 0.052(2) 0.0005(16) 0.0046(15) 0.0035(15)
C6 0.0376(17) 0.064(3) 0.060(2) 0.0078(19) -0.0041(16) -0.0063(18)
C7 0.0482(19) 0.042(2) 0.054(2) 0.0026(16) -0.0025(16) -0.0128(17)
C8 0.055(2) 0.045(2) 0.054(2) 0.0098(17) -0.0046(17) 0.0062(18)
C9 0.067(3) 0.043(2) 0.084(3) 0.022(2) -0.017(2) 0.009(2)
C10 0.059(2) 0.030(2) 0.089(3) 0.010(2) -0.003(2) 0.0077(17)
C11 0.062(2) 0.050(2) 0.049(2) -0.0014(17) -0.0124(17) -0.0001(19)
C12 0.061(3) 0.121(5) 0.062(3) -0.006(3) -0.014(2) -0.010(3)
B1 0.047(2) 0.028(2) 0.059(2) -0.0096(17) -0.0025(18) 0.0000(16)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C1 1.813(4) . ?
Ru1 N3 2.106(3) . ?
Ru1 N5 2.124(3) . ?
Ru1 N1 2.189(3) . ?
Ru1 S1 2.4129(9) 3_756 ?
Ru1 S1 2.4148(9) . ?
S1 C11 1.836(4) . ?
S1 Ru1 2.4129(9) 3_756 ?
O1 C1 1.157(5) . ?
N1 C2 1.325(5) . ?
N1 N2 1.374(4) . ?
N2 C4 1.348(5) . ?
N2 B1 1.544(6) . ?
N3 C5 1.334(4) . ?
N3 N4 1.361(4) . ?
N4 C7 1.345(4) . ?
N4 B1 1.532(5) . ?
N5 C8 1.339(5) . ?
N5 N6 1.347(4) . ?
N6 C10 1.349(5) . ?
N6 B1 1.530(5) . ?
C2 C3 1.404(6) . ?
C3 C4 1.360(7) . ?
C5 C6 1.394(6) . ?
C6 C7 1.361(6) . ?
C8 C9 1.380(6) . ?
C9 C10 1.374(7) . ?
C11 C12 1.480(6) . ?

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
C1 Ru1 N3 90.62(14) . . ?
C1 Ru1 N5 88.78(13) . . ?
N3 Ru1 N5 86.59(11) . . ?
C1 Ru1 N1 170.29(13) . . ?
N3 Ru1 N1 86.36(11) . . ?
N5 Ru1 N1 81.84(11) . . ?
C1 Ru1 S1 92.09(11) . 3_756 ?
N3 Ru1 S1 93.85(8) . 3_756 ?
N5 Ru1 S1 179.02(8) . 3_756 ?
N1 Ru1 S1 97.31(8) . 3_756 ?
C1 Ru1 S1 94.16(12) . . ?
N3 Ru1 S1 173.28(9) . . ?
N5 Ru1 S1 98.22(8) . . ?
N1 Ru1 S1 89.66(8) . . ?
S1 Ru1 S1 81.27(3) 3_756 . ?
C11 S1 Ru1 108.43(14) . 3_756 ?
C11 S1 Ru1 109.91(14) . . ?
Ru1 S1 Ru1 98.73(3) 3_756 . ?
C2 N1 N2 106.1(3) . . ?
C2 N1 Ru1 136.0(3) . . ?
N2 N1 Ru1 117.3(2) . . ?
C4 N2 N1 109.4(3) . . ?
C4 N2 B1 129.4(3) . . ?
N1 N2 B1 120.2(3) . . ?
C5 N3 N4 106.8(3) . . ?
C5 N3 Ru1 132.8(3) . . ?
N4 N3 Ru1 120.3(2) . . ?
C7 N4 N3 108.6(3) . . ?
C7 N4 B1 132.0(3) . . ?
N3 N4 B1 119.4(3) . . ?
C8 N5 N6 106.5(3) . . ?
C8 N5 Ru1 134.1(3) . . ?
N6 N5 Ru1 119.2(2) . . ?
N5 N6 C10 109.8(3) . . ?
N5 N6 B1 120.6(3) . . ?
C10 N6 B1 129.6(3) . . ?
O1 C1 Ru1 174.1(3) . . ?
N1 C2 C3 110.8(4) . . ?
C4 C3 C2 104.7(4) . . ?
N2 C4 C3 109.0(4) . . ?
N3 C5 C6 110.4(4) . . ?
C7 C6 C5 104.3(3) . . ?
N4 C7 C6 109.9(4) . . ?
N5 C8 C9 110.5(4) . . ?
C10 C9 C8 105.0(4) . . ?
N6 C10 C9 108.2(4) . . ?
C12 C11 S1 113.1(3) . . ?
N6 B1 N4 109.1(3) . . ?
N6 B1 N2 106.7(3) . . ?
N4 B1 N2 109.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         1.562
_refine_diff_density_min         -0.972
_refine_diff_density_rms         0.121