# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zhj20141210
_database_code_depnum_ccdc_archive 'CCDC 1038973'
_audit_update_record             
;
2014-12-12 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;
_audit_creation_date             2014-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 Cl2 N P Ru S'
_chemical_formula_sum            'C29 H28 Cl2 N P Ru S'
_chemical_formula_weight         625.52
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru 0.0552 3.2960 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   12.6476(3)
_cell_length_b                   11.7959(3)
_cell_length_c                   18.6459(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.933(2)
_cell_angle_gamma                90
_cell_volume                     2711.22(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5131
_cell_measurement_temperature    152.95(10)
_cell_measurement_theta_max      62.2520
_cell_measurement_theta_min      3.8550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.912
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10535
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        62.106
_diffrn_reflns_theta_max         62.106
_diffrn_reflns_theta_min         3.856
_diffrn_ambient_temperature      152.95(10)
_diffrn_detector_area_resol_mean 16.1903
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -110.00  -78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.3066 -178.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  2 omega  -64.00   11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.3066   82.0000  -27.0000 75

#__ type_ start__ end____ width___ exp.time_
  3 omega   33.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3066 -178.0000  -60.0000 78

#__ type_ start__ end____ width___ exp.time_
  4 omega  -29.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3066  -57.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega   51.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3066   57.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
  6 omega   19.00   59.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -25.0000   90.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega   95.00  121.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000    0.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   34.00   71.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -25.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  9 omega   58.00   83.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -50.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   40.00   71.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  178.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
 11 omega   52.00  104.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -77.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega  131.00  161.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000    0.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
 13 omega   51.00  123.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -77.0000  120.0000 72

#__ type_ start__ end____ width___ exp.time_
 14 omega   22.00   53.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -38.0000   30.0000 31

#__ type_ start__ end____ width___ exp.time_
 15 omega   29.00   82.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -50.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
 16 omega  106.00  131.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  178.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega   24.00   69.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -38.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
 18 omega   29.00   63.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -25.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
 19 omega   24.00   83.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -50.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
 20 omega   91.00  116.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  178.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 21 omega   21.00   59.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000 -112.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
 22 omega   69.00   99.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  178.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 23 omega   19.00   68.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -25.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
 24 omega   40.00   69.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -38.0000  150.0000 29
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1206242000
_diffrn_orient_matrix_UB_12      -0.0217845000
_diffrn_orient_matrix_UB_13      -0.0016732000
_diffrn_orient_matrix_UB_21      0.0121745000
_diffrn_orient_matrix_UB_22      0.0632773000
_diffrn_orient_matrix_UB_23      0.0736890000
_diffrn_orient_matrix_UB_31      -0.0303015000
_diffrn_orient_matrix_UB_32      0.1121379000
_diffrn_orient_matrix_UB_33      -0.0418943000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3990
_reflns_number_total             4259
_reflns_odcompleteness_completeness 77.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.550
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.550
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1211
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.09081(2) 0.88152(2) 0.39507(2) 0.01733(15) Uani 1 1 d . . . . .
Cl2 Cl 0.18962(8) 0.80235(9) 0.50914(5) 0.0292(2) Uani 1 1 d . . . . .
Cl1 Cl -0.06560(7) 0.77750(8) 0.40999(6) 0.0261(2) Uani 1 1 d . . . . .
S1 S 0.34888(8) 0.57532(10) 0.38816(6) 0.0316(3) Uani 1 1 d . . . . .
P1 P 0.14129(7) 0.72103(8) 0.33767(5) 0.0173(2) Uani 1 1 d . . . . .
C8 C -0.1823(4) 0.9417(5) 0.2448(3) 0.0441(12) Uani 1 1 d . . . . .
C10 C 0.3305(4) 1.0136(4) 0.4392(3) 0.0411(12) Uani 1 1 d . . . . .
C9 C -0.1707(4) 1.1464(5) 0.2874(3) 0.0438(12) Uani 1 1 d . . . . .
C122 C -0.0100(4) 0.7153(5) 0.2068(3) 0.0384(11) Uani 1 1 d . . . . .
C136 C 0.5788(4) 0.5881(6) 0.4185(3) 0.0476(14) Uani 1 1 d . . . . .
C121 C 0.1005(3) 0.7320(3) 0.2377(2) 0.0230(8) Uani 1 1 d . . . . .
C7 C -0.1393(3) 1.0223(4) 0.3093(2) 0.0311(10) Uani 1 1 d . . . . .
C123 C -0.0493(5) 0.7317(5) 0.1317(3) 0.0522(14) Uani 1 1 d . . . . .
C115 C 0.0622(5) 0.3828(4) 0.3212(3) 0.0446(13) Uani 1 1 d . . . . .
C114 C 0.0576(4) 0.3555(4) 0.3929(3) 0.0414(12) Uani 1 1 d . . . . .
C126 C 0.1698(4) 0.7646(4) 0.1940(2) 0.0331(10) Uani 1 1 d . . . . .
C2 C 0.0561(3) 0.9898(3) 0.2959(2) 0.0244(9) Uani 1 1 d . . . . .
C5 C 0.1347(4) 1.0522(3) 0.4443(2) 0.0283(9) Uani 1 1 d . . . . .
C113 C 0.0761(4) 0.4380(4) 0.4464(3) 0.0345(10) Uani 1 1 d . . . . .
C6 C 0.0232(4) 1.0527(3) 0.4140(2) 0.0264(9) Uani 1 1 d . . . . .
C2AA C -0.0188(3) 1.0190(3) 0.3384(2) 0.0252(9) Uani 1 1 d . . . . .
C125 C 0.1288(5) 0.7820(5) 0.1188(3) 0.0485(14) Uani 1 1 d . . . . .
C4 C 0.2113(3) 1.0186(4) 0.4024(3) 0.0286(9) Uani 1 1 d . . . . .
N1 N 0.3542(3) 0.7858(3) 0.3491(2) 0.0282(8) Uani 1 1 d . . . . .
C112 C 0.0981(3) 0.5492(4) 0.4301(3) 0.0288(9) Uani 1 1 d . . . . .
C135 C 0.6664(4) 0.6597(7) 0.4187(3) 0.0555(17) Uani 1 1 d . . . . .
C137 C 0.4746(4) 0.6369(5) 0.3935(2) 0.0338(11) Uani 1 1 d . . . . .
C111 C 0.1028(3) 0.5768(4) 0.3579(2) 0.0224(8) Uani 1 1 d . . . . .
C124 C 0.0190(6) 0.7649(5) 0.0883(3) 0.0542(16) Uani 1 1 d . . . . .
C116 C 0.0859(4) 0.4933(4) 0.3037(3) 0.0330(10) Uani 1 1 d . . . . .
C131 C 0.2888(3) 0.7039(4) 0.3558(2) 0.0222(8) Uani 1 1 d . . . . .
C3 C 0.1710(3) 0.9889(4) 0.3286(2) 0.0259(9) Uani 1 1 d . . . . .
C133 C 0.5518(4) 0.8189(5) 0.3717(3) 0.0442(13) Uani 1 1 d . . . . .
C134 C 0.6543(4) 0.7717(7) 0.3964(3) 0.0556(17) Uani 1 1 d . . . . .
C132 C 0.4611(3) 0.7499(4) 0.3709(2) 0.0311(10) Uani 1 1 d . . . . .


_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 Cl2 2.4017(10) . ?
Ru1 Cl1 2.3964(9) . ?
Ru1 P1 2.3329(10) . ?
Ru1 C2 2.209(4) . ?
Ru1 C5 2.231(4) . ?
Ru1 C6 2.251(4) . ?
Ru1 C2AA 2.239(4) . ?
Ru1 C4 2.205(4) . ?
Ru1 C3 2.175(4) . ?
S1 C137 1.731(5) . ?
S1 C131 1.742(4) . ?
P1 C121 1.824(4) . ?
P1 C111 1.832(4) . ?
P1 C131 1.831(4) . ?
C8 C7 1.534(7) . ?
C10 C4 1.511(6) . ?
C9 C7 1.548(7) . ?
C122 C121 1.402(6) . ?
C122 C123 1.390(7) . ?
C136 C135 1.392(10) . ?
C136 C137 1.417(7) . ?
C121 C126 1.378(6) . ?
C7 C2AA 1.500(6) . ?
C123 C124 1.366(10) . ?
C115 C114 1.389(8) . ?
C115 C116 1.393(7) . ?
C114 C113 1.376(8) . ?
C126 C125 1.397(7) . ?
C2 C2AA 1.407(6) . ?
C2 C3 1.444(6) . ?
C5 C6 1.397(6) . ?
C5 C4 1.430(6) . ?
C113 C112 1.389(7) . ?
C6 C2AA 1.447(6) . ?
C125 C124 1.393(9) . ?
C4 C3 1.400(6) . ?
N1 C131 1.297(6) . ?
N1 C132 1.388(6) . ?
C112 C111 1.398(7) . ?
C135 C134 1.384(10) . ?
C137 C132 1.397(8) . ?
C111 C116 1.394(7) . ?
C133 C134 1.391(8) . ?
C133 C132 1.404(7) . ?

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
Cl1 Ru1 Cl2 88.71(4) . . ?
P1 Ru1 Cl2 87.08(4) . . ?
P1 Ru1 Cl1 87.45(3) . . ?
C2 Ru1 Cl2 158.84(11) . . ?
C2 Ru1 Cl1 112.27(11) . . ?
C2 Ru1 P1 96.25(11) . . ?
C2 Ru1 C5 78.88(16) . . ?
C2 Ru1 C6 66.48(15) . . ?
C2 Ru1 C2AA 36.87(15) . . ?
C2 Ru1 C4 68.45(16) . . ?
C5 Ru1 Cl2 87.37(12) . . ?
C5 Ru1 Cl1 123.38(11) . . ?
C5 Ru1 P1 148.50(11) . . ?
C5 Ru1 C6 36.32(16) . . ?
C5 Ru1 C2AA 67.15(16) . . ?
C6 Ru1 Cl2 110.53(11) . . ?
C6 Ru1 Cl1 95.11(11) . . ?
C6 Ru1 P1 162.22(11) . . ?
C2AA Ru1 Cl2 147.59(11) . . ?
C2AA Ru1 Cl1 89.18(11) . . ?
C2AA Ru1 P1 125.11(11) . . ?
C2AA Ru1 C6 37.59(16) . . ?
C4 Ru1 Cl2 90.86(12) . . ?
C4 Ru1 Cl1 160.96(12) . . ?
C4 Ru1 P1 111.54(12) . . ?
C4 Ru1 C5 37.61(17) . . ?
C4 Ru1 C6 67.28(15) . . ?
C4 Ru1 C2AA 81.05(16) . . ?
C3 Ru1 Cl2 120.96(12) . . ?
C3 Ru1 Cl1 150.07(12) . . ?
C3 Ru1 P1 90.06(11) . . ?
C3 Ru1 C2 38.45(16) . . ?
C3 Ru1 C5 66.67(16) . . ?
C3 Ru1 C6 78.94(15) . . ?
C3 Ru1 C2AA 68.13(15) . . ?
C3 Ru1 C4 37.27(17) . . ?
C137 S1 C131 88.8(2) . . ?
C121 P1 Ru1 111.56(13) . . ?
C121 P1 C111 104.41(19) . . ?
C121 P1 C131 103.89(18) . . ?
C111 P1 Ru1 123.12(13) . . ?
C111 P1 C131 99.56(18) . . ?
C131 P1 Ru1 112.15(14) . . ?
C123 C122 C121 119.6(5) . . ?
C135 C136 C137 115.8(6) . . ?
C122 C121 P1 116.0(3) . . ?
C126 C121 P1 123.5(3) . . ?
C126 C121 C122 120.3(4) . . ?
C8 C7 C9 110.8(4) . . ?
C2AA C7 C8 114.9(4) . . ?
C2AA C7 C9 107.4(4) . . ?
C124 C123 C122 120.3(5) . . ?
C114 C115 C116 120.0(5) . . ?
C113 C114 C115 119.9(5) . . ?
C121 C126 C125 119.5(5) . . ?
C2AA C2 Ru1 72.7(2) . . ?
C2AA C2 C3 120.3(4) . . ?
C3 C2 Ru1 69.5(2) . . ?
C6 C5 Ru1 72.6(2) . . ?
C6 C5 C4 121.7(4) . . ?
C4 C5 Ru1 70.2(2) . . ?
C114 C113 C112 121.2(5) . . ?
C5 C6 Ru1 71.1(2) . . ?
C5 C6 C2AA 120.8(4) . . ?
C2AA C6 Ru1 70.8(2) . . ?
C7 C2AA Ru1 131.4(3) . . ?
C2 C2AA Ru1 70.4(2) . . ?
C2 C2AA C7 124.2(4) . . ?
C2 C2AA C6 117.9(4) . . ?
C6 C2AA Ru1 71.7(2) . . ?
C6 C2AA C7 117.8(4) . . ?
C124 C125 C126 120.1(5) . . ?
C10 C4 Ru1 127.2(3) . . ?
C5 C4 Ru1 72.2(2) . . ?
C5 C4 C10 119.4(4) . . ?
C3 C4 Ru1 70.2(2) . . ?
C3 C4 C10 122.9(4) . . ?
C3 C4 C5 117.7(4) . . ?
C131 N1 C132 110.2(4) . . ?
C113 C112 C111 119.0(4) . . ?
C136 C135 C134 123.0(5) . . ?
C136 C137 S1 128.6(5) . . ?
C132 C137 S1 109.5(3) . . ?
C132 C137 C136 121.9(5) . . ?
C112 C111 P1 119.0(3) . . ?
C116 C111 P1 120.7(3) . . ?
C116 C111 C112 120.1(4) . . ?
C123 C124 C125 120.3(5) . . ?
C111 C116 C115 119.8(4) . . ?
S1 C131 P1 120.5(2) . . ?
N1 C131 S1 116.3(3) . . ?
N1 C131 P1 123.1(3) . . ?
C2 C3 Ru1 72.0(2) . . ?
C4 C3 Ru1 72.5(2) . . ?
C4 C3 C2 121.6(4) . . ?
C134 C133 C132 118.0(6) . . ?
C133 C134 C135 120.9(5) . . ?
N1 C132 C137 115.1(4) . . ?
N1 C132 C133 124.5(5) . . ?
C137 C132 C133 120.4(4) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2014-12-11
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lwd2014100101
_database_code_depnum_ccdc_archive 'CCDC 1039491'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;
_audit_creation_date             2014-10-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H12 N O P S'
_chemical_formula_sum            'C15 H12 N O P S'
_chemical_formula_weight         285.29
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.4363(4)
_cell_length_b                   13.1058(5)
_cell_length_c                   20.7087(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.816(3)
_cell_angle_gamma                90.00
_cell_volume                     2812.44(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2719
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.1290
_cell_measurement_theta_min      3.6790
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10142
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.26
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.1903
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -39.00   50.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6309   57.0000  -30.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega  -42.00   49.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6309   57.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega  -36.00   50.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6309   57.0000 -150.0000 86

#__ type_ start__ end____ width___ exp.time_
  4 omega  -23.00   11.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6309  -77.0000   90.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega   54.00  104.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0372 -178.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00   58.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0372   57.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega  -15.00   34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0372   85.0000  -68.0000 49

#__ type_ start__ end____ width___ exp.time_
  8 omega   11.00   37.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0372  -57.0000  -30.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0517973000
_diffrn_orient_matrix_UB_12      -0.0079838000
_diffrn_orient_matrix_UB_13      0.0187143000
_diffrn_orient_matrix_UB_21      -0.0294568000
_diffrn_orient_matrix_UB_22      -0.0336297000
_diffrn_orient_matrix_UB_23      -0.0241944000
_diffrn_orient_matrix_UB_31      0.0337048000
_diffrn_orient_matrix_UB_32      -0.0416392000
_diffrn_orient_matrix_UB_33      0.0159450000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2438
_reflns_number_total             2761
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2761
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.027
_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)+(0.0500P)²+2.3050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1026
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C14(H14), C13(H13), C7(H7), C11(H11), C2(H2), C6(H6), C3(H3),
 C12(H12), C8(H8), C5(H5), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
P1 P 0.83703(5) 0.55109(3) 0.37910(2) 0.02511(15) Uani 1 d . . .
S1 S 0.65026(6) 0.56961(4) 0.48010(3) 0.04223(18) Uani 1 d . . .
O1 O 0.86829(14) 0.45661(10) 0.41705(7) 0.0383(4) Uani 1 d . . .
N1 N 0.67179(17) 0.71345(12) 0.39881(8) 0.0364(4) Uani 1 d . . .
C9 C 0.8221(3) 0.44419(19) 0.26564(13) 0.0613(7) Uani 1 d . . .
H9 H 0.8824 0.4017 0.2888 0.074 Uiso 1 calc . . R
C14 C 1.1833(2) 0.67908(17) 0.43100(11) 0.0445(5) Uani 1 d . . .
H14 H 1.2537 0.6660 0.4618 0.053 Uiso 1 calc . . R
C13 C 1.1859(2) 0.76153(17) 0.39008(11) 0.0455(6) Uani 1 d . . .
H13 H 1.2579 0.8038 0.3932 0.055 Uiso 1 calc . . R
C7 C 0.6908(4) 0.4843(4) 0.16778(15) 0.0928(14) Uani 1 d . . .
H7 H 0.6617 0.4688 0.1247 0.111 Uiso 1 calc . . R
C11 C 0.9749(2) 0.71846(15) 0.33910(10) 0.0369(5) Uani 1 d . . .
H11 H 0.9051 0.7316 0.3080 0.044 Uiso 1 calc . . R
C2 C 0.5607(2) 0.67675(17) 0.48568(10) 0.0423(5) Uani 1 d . . .
H2 H 0.5036 0.6873 0.5163 0.051 Uiso 1 calc . . R
C6 C 0.6441(3) 0.5677(3) 0.19557(14) 0.0940(13) Uani 1 d . . .
H6 H 0.5837 0.6092 0.1717 0.113 Uiso 1 calc . . R
C3 C 0.5839(2) 0.74409(16) 0.43968(10) 0.0401(5) Uani 1 d . . .
H3 H 0.5434 0.8074 0.4356 0.048 Uiso 1 calc . . R
C10 C 0.97261(17) 0.63541(13) 0.38041(8) 0.0250(4) Uani 1 d . . .
C1 C 0.71457(17) 0.62222(13) 0.41495(8) 0.0252(4) Uani 1 d . . .
C4 C 0.77529(19) 0.52873(15) 0.29543(9) 0.0334(4) Uani 1 d . . .
C12 C 1.0819(2) 0.78163(16) 0.34449(11) 0.0447(5) Uani 1 d . . .
H12 H 1.0836 0.8378 0.3172 0.054 Uiso 1 calc . . R
C8 C 0.7789(5) 0.4231(3) 0.20152(18) 0.0914(13) Uani 1 d . . .
H8 H 0.8106 0.3666 0.1814 0.110 Uiso 1 calc . . R
C5 C 0.6869(3) 0.5909(3) 0.26011(12) 0.0651(8) Uani 1 d . . .
H5 H 0.6557 0.6484 0.2793 0.078 Uiso 1 calc . . R
C15 C 1.07743(19) 0.61569(15) 0.42668(10) 0.0340(4) Uani 1 d . . .
H15 H 1.0760 0.5601 0.4545 0.041 Uiso 1 calc . . R


_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
P1 O1 1.4820(14) . ?
P1 C10 1.7930(17) . ?
P1 C1 1.8107(19) . ?
P1 C4 1.7995(19) . ?
S1 C2 1.698(2) . ?
S1 C1 1.7208(18) . ?
N1 C3 1.379(3) . ?
N1 C1 1.306(2) . ?
C9 C4 1.385(3) . ?
C9 C8 1.379(5) . ?
C14 C13 1.375(3) . ?
C14 C15 1.377(3) . ?
C13 C12 1.376(3) . ?
C7 C6 1.352(5) . ?
C7 C8 1.351(6) . ?
C11 C10 1.386(3) . ?
C11 C12 1.384(3) . ?
C2 C3 1.342(3) . ?
C6 C5 1.392(4) . ?
C10 C15 1.390(3) . ?
C4 C5 1.374(3) . ?

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
O1 P1 C10 112.54(8) . . ?
O1 P1 C1 109.54(8) . . ?
O1 P1 C4 113.93(9) . . ?
C10 P1 C1 105.70(8) . . ?
C10 P1 C4 107.86(8) . . ?
C4 P1 C1 106.80(9) . . ?
C2 S1 C1 89.49(10) . . ?
C1 N1 C3 109.97(17) . . ?
C8 C9 C4 119.8(3) . . ?
C13 C14 C15 120.5(2) . . ?
C14 C13 C12 120.11(19) . . ?
C8 C7 C6 121.1(3) . . ?
C12 C11 C10 119.53(19) . . ?
C3 C2 S1 110.37(16) . . ?
C7 C6 C5 119.6(4) . . ?
C2 C3 N1 115.69(19) . . ?
C11 C10 P1 123.10(14) . . ?
C11 C10 C15 120.09(17) . . ?
C15 C10 P1 116.80(14) . . ?
S1 C1 P1 118.36(10) . . ?
N1 C1 P1 127.09(14) . . ?
N1 C1 S1 114.47(14) . . ?
C9 C4 P1 117.03(19) . . ?
C5 C4 P1 123.85(17) . . ?
C5 C4 C9 119.1(2) . . ?
C13 C12 C11 120.2(2) . . ?
C7 C8 C9 120.3(3) . . ?
C4 C5 C6 120.0(3) . . ?
C14 C15 C10 119.49(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
