# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_fh1

_audit_creation_date             2012-01-16T12:53:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H12 Cl3 N4 O1 Rh1 S1'
_chemical_formula_sum            'C9 H12 Cl3 N4 O Rh S'
_chemical_formula_weight         433.55
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
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'

_cell_length_a                   16.6279(16)
_cell_length_b                   16.2342(10)
_cell_length_c                   13.1308(12)
_cell_angle_alpha                90.0
_cell_angle_beta                 122.054(13)
_cell_angle_gamma                90.0
_cell_volume                     3004.2(6)
_cell_measurement_reflns_used    4069
_cell_measurement_theta_min      3.1000
_cell_measurement_theta_max      29.0903
_cell_oxdiff_length_a            16.6325(11)
_cell_oxdiff_length_b            16.2413(9)
_cell_oxdiff_length_c            13.1306(9)
_cell_oxdiff_angle_alpha         89.846(5)
_cell_oxdiff_angle_beta          122.119(7)
_cell_oxdiff_angle_gamma         90.000(5)
_cell_oxdiff_volume              3004.1(3)
_cell_oxdiff_measurement_reflns_used 4068
_cell_formula_units_Z            8
_cell_measurement_temperature    183(2)
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_correction_T_min  0.92832
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      183(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 15.9853
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_number            10538
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             2848
_reflns_number_gt                2393
_reflns_threshold_expression     >2σ(I)
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_theta     26.32
_reflns_odcompleteness_iscentric 1

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0384P)²+2.9455P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2848
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.044
_refine_ls_wR_factor_ref         0.092
_refine_ls_wR_factor_gt          0.087
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.895
_refine_diff_density_min         -0.38
_refine_diff_density_rms         0.078

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Rh1 Rh 0.25939(2) 0.12010(2) 0.72781(3) 0.04172(14) Uani 1 1 d . . .
S1 S 0.11912(9) 0.13295(8) 0.55176(11) 0.0567(3) Uani 1 1 d . . .
O1S O 0.0404(3) 0.1514(3) 0.5660(4) 0.0931(14) Uani 1 1 d . . .
C1S C 0.0893(4) 0.0443(4) 0.4594(5) 0.092(2) Uani 1 1 d . . .
H1S1 H 0.0873 -0.004 0.5028 0.139 Uiso 1 1 calc R . .
H1S2 H 0.1371 0.0357 0.4384 0.139 Uiso 1 1 calc R . .
H1S3 H 0.027 0.0521 0.3858 0.139 Uiso 1 1 calc R . .
C2S C 0.1227(4) 0.2065(4) 0.4568(5) 0.0775(18) Uani 1 1 d . . .
H2S1 H 0.0596 0.2119 0.3839 0.116 Uiso 1 1 calc R . .
H2S2 H 0.1681 0.1891 0.4351 0.116 Uiso 1 1 calc R . .
H2S3 H 0.1425 0.2597 0.4983 0.116 Uiso 1 1 calc R . .
Cl1 Cl 0.22721(9) -0.01814(8) 0.74113(11) 0.0600(3) Uani 1 1 d . . .
Cl2 Cl 0.32987(9) 0.08707(9) 0.62056(11) 0.0601(4) Uani 1 1 d . . .
Cl3 Cl 0.29169(10) 0.26033(8) 0.73269(11) 0.0642(4) Uani 1 1 d . . .
N1 N 0.2818(3) 0.1345(2) 0.9575(3) 0.0526(10) Uani 1 1 d . . .
N2 N 0.2135(3) 0.1440(2) 0.8402(3) 0.0491(10) Uani 1 1 d . . .
C3 C 0.1348(4) 0.1618(4) 0.8350(5) 0.0634(14) Uani 1 1 d . . .
H3 H 0.0755 0.1717 0.763 0.076 Uiso 1 1 calc R . .
C4 C 0.1502(4) 0.1644(4) 0.9515(5) 0.0656(15) Uani 1 1 d . . .
H4 H 0.1044 0.1754 0.9719 0.079 Uiso 1 1 calc R . .
C5 C 0.2444(4) 0.1477(3) 1.0291(5) 0.0700(16) Uani 1 1 d . . .
H5 H 0.2774 0.1455 1.1143 0.084 Uiso 1 1 calc R . .
N6 N 0.4399(3) 0.1180(3) 1.1016(4) 0.0677(13) Uani 1 1 d . . .
C7 C 0.3742(3) 0.1197(3) 0.9873(4) 0.0484(11) Uani 1 1 d . . .
N8 N 0.3840(3) 0.1115(2) 0.8929(3) 0.0439(9) Uani 1 1 d . . .
C9 C 0.4727(3) 0.1034(3) 0.9192(4) 0.0493(12) Uani 1 1 d . . .
H9 H 0.4846 0.0994 0.8561 0.059 Uiso 1 1 calc R . .
C10 C 0.5473(3) 0.1006(3) 1.0368(4) 0.0551(13) Uani 1 1 d . . .
H10 H 0.6109 0.0944 1.0568 0.066 Uiso 1 1 calc R . .
C11 C 0.5263(4) 0.1072(3) 1.1228(5) 0.0683(15) Uani 1 1 d . . .
H11 H 0.5772 0.1038 1.2042 0.082 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Rh1 N2 2.026(4) . ?
Rh1 N8 2.061(4) . ?
Rh1 S1 2.2593(14) . ?
Rh1 Cl2 2.3230(12) . ?
Rh1 Cl3 2.3320(13) . ?
Rh1 Cl1 2.3350(13) . ?
S1 O1S 1.449(4) . ?
S1 C2S 1.750(5) . ?
S1 C1S 1.775(6) . ?
C1S H1S1 0.98 . ?
C1S H1S2 0.98 . ?
C1S H1S3 0.98 . ?
C2S H2S1 0.98 . ?
C2S H2S2 0.98 . ?
C2S H2S3 0.98 . ?
N1 N2 1.353(5) . ?
N1 C7 1.390(6) . ?
N1 C5 1.392(6) . ?
N2 C3 1.307(6) . ?
C3 C4 1.410(7) . ?
C3 H3 0.95 . ?
C4 C5 1.367(7) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?
N6 C7 1.306(6) . ?
N6 C11 1.321(7) . ?
C7 N8 1.341(6) . ?
N8 C9 1.330(6) . ?
C9 C10 1.376(6) . ?
C9 H9 0.95 . ?
C10 C11 1.351(7) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?

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
N2 Rh1 N8 78.69(15) . . ?
N2 Rh1 S1 98.30(12) . . ?
N8 Rh1 S1 176.90(11) . . ?
N2 Rh1 Cl2 172.69(12) . . ?
N8 Rh1 Cl2 94.17(11) . . ?
S1 Rh1 Cl2 88.85(5) . . ?
N2 Rh1 Cl3 87.90(11) . . ?
N8 Rh1 Cl3 87.09(10) . . ?
S1 Rh1 Cl3 92.04(5) . . ?
Cl2 Rh1 Cl3 93.39(5) . . ?
N2 Rh1 Cl1 86.54(12) . . ?
N8 Rh1 Cl1 89.90(10) . . ?
S1 Rh1 Cl1 90.70(5) . . ?
Cl2 Rh1 Cl1 91.89(5) . . ?
Cl3 Rh1 Cl1 174.10(5) . . ?
O1S S1 C2S 109.0(3) . . ?
O1S S1 C1S 108.2(3) . . ?
C2S S1 C1S 99.7(3) . . ?
O1S S1 Rh1 113.58(17) . . ?
C2S S1 Rh1 112.63(19) . . ?
C1S S1 Rh1 112.8(2) . . ?
S1 C1S H1S1 109.5 . . ?
S1 C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
S1 C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
S1 C2S H2S1 109.5 . . ?
S1 C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
S1 C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
N2 N1 C7 118.3(4) . . ?
N2 N1 C5 110.2(4) . . ?
C7 N1 C5 131.3(4) . . ?
C3 N2 N1 107.3(4) . . ?
C3 N2 Rh1 139.3(4) . . ?
N1 N2 Rh1 113.3(3) . . ?
N2 C3 C4 110.4(5) . . ?
N2 C3 H3 124.8 . . ?
C4 C3 H3 124.8 . . ?
C5 C4 C3 106.3(4) . . ?
C5 C4 H4 126.9 . . ?
C3 C4 H4 126.9 . . ?
C4 C5 N1 105.8(5) . . ?
C4 C5 H5 127.1 . . ?
N1 C5 H5 127.1 . . ?
C7 N6 C11 113.5(4) . . ?
N6 C7 N8 128.4(5) . . ?
N6 C7 N1 116.9(4) . . ?
N8 C7 N1 114.6(4) . . ?
C9 N8 C7 115.6(4) . . ?
C9 N8 Rh1 129.6(3) . . ?
C7 N8 Rh1 114.7(3) . . ?
N8 C9 C10 120.6(4) . . ?
N8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 117.2(5) . . ?
C11 C10 H10 121.4 . . ?
C9 C10 H10 121.4 . . ?
N6 C11 C10 124.6(5) . . ?
N6 C11 H11 117.7 . . ?
C10 C11 H11 117.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Rh1 S1 O1S -1.2(3) . . . . ?
Cl2 Rh1 S1 O1S 177.2(2) . . . . ?
Cl3 Rh1 S1 O1S -89.4(2) . . . . ?
Cl1 Rh1 S1 O1S 85.4(2) . . . . ?
N2 Rh1 S1 C2S 123.3(3) . . . . ?
Cl2 Rh1 S1 C2S -58.2(2) . . . . ?
Cl3 Rh1 S1 C2S 35.1(2) . . . . ?
Cl1 Rh1 S1 C2S -150.1(2) . . . . ?
N2 Rh1 S1 C1S -124.8(3) . . . . ?
Cl2 Rh1 S1 C1S 53.7(2) . . . . ?
Cl3 Rh1 S1 C1S 147.0(2) . . . . ?
Cl1 Rh1 S1 C1S -38.2(2) . . . . ?
C7 N1 N2 C3 -176.3(4) . . . . ?
C5 N1 N2 C3 -0.5(6) . . . . ?
C7 N1 N2 Rh1 7.2(5) . . . . ?
C5 N1 N2 Rh1 -176.9(3) . . . . ?
N8 Rh1 N2 C3 179.4(6) . . . . ?
S1 Rh1 N2 C3 0.2(6) . . . . ?
Cl3 Rh1 N2 C3 92.0(6) . . . . ?
Cl1 Rh1 N2 C3 -90.0(6) . . . . ?
N8 Rh1 N2 N1 -5.8(3) . . . . ?
S1 Rh1 N2 N1 175.0(3) . . . . ?
Cl3 Rh1 N2 N1 -93.3(3) . . . . ?
Cl1 Rh1 N2 N1 84.8(3) . . . . ?
N1 N2 C3 C4 -0.1(6) . . . . ?
Rh1 N2 C3 C4 174.9(4) . . . . ?
N2 C3 C4 C5 0.6(7) . . . . ?
C3 C4 C5 N1 -0.9(6) . . . . ?
N2 N1 C5 C4 0.9(6) . . . . ?
C7 N1 C5 C4 176.0(5) . . . . ?
C11 N6 C7 N8 0.6(8) . . . . ?
C11 N6 C7 N1 -177.3(5) . . . . ?
N2 N1 C7 N6 174.2(4) . . . . ?
C5 N1 C7 N6 -0.6(8) . . . . ?
N2 N1 C7 N8 -4.0(6) . . . . ?
C5 N1 C7 N8 -178.7(5) . . . . ?
N6 C7 N8 C9 -2.7(7) . . . . ?
N1 C7 N8 C9 175.2(4) . . . . ?
N6 C7 N8 Rh1 -179.2(4) . . . . ?
N1 C7 N8 Rh1 -1.3(5) . . . . ?
N2 Rh1 N8 C9 -172.0(4) . . . . ?
Cl2 Rh1 N8 C9 9.6(4) . . . . ?
Cl3 Rh1 N8 C9 -83.6(4) . . . . ?
Cl1 Rh1 N8 C9 101.5(4) . . . . ?
N2 Rh1 N8 C7 3.9(3) . . . . ?
Cl2 Rh1 N8 C7 -174.5(3) . . . . ?
Cl3 Rh1 N8 C7 92.3(3) . . . . ?
Cl1 Rh1 N8 C7 -82.6(3) . . . . ?
C7 N8 C9 C10 2.5(6) . . . . ?
Rh1 N8 C9 C10 178.4(3) . . . . ?
N8 C9 C10 C11 -0.5(7) . . . . ?
C7 N6 C11 C10 1.7(8) . . . . ?
C9 C10 C11 N6 -1.7(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 O1S 0.95 2.35 3.014(6) 126.3 .
C9 H9 Cl2 0.95 2.79 3.347(5) 118.4 .

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 963267'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_pm180

_audit_creation_date             2012-06-13T18:27:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H18 Cl1 N4 O1 Ru1 S1'
_chemical_formula_sum            'C9 H12 Cl3 N4 O Ru S'
_chemical_formula_weight         431.71
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
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'

_cell_length_a                   16.718(5)
_cell_length_b                   16.230(4)
_cell_length_c                   13.167(4)
_cell_angle_alpha                90
_cell_angle_beta                 122.42(2)
_cell_angle_gamma                90
_cell_volume                     3015.8(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      7
_cell_measurement_theta_max      11
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.902
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1704
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.705
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.4842
_exptl_absorpt_correction_T_max  0.699

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      0.027309
_diffrn_orient_matrix_ub_12      0.048977
_diffrn_orient_matrix_ub_13      0.054108
_diffrn_orient_matrix_ub_21      -0.063146
_diffrn_orient_matrix_ub_22      0.027865
_diffrn_orient_matrix_ub_23      -0.045639
_diffrn_orient_matrix_ub_31      -0.016975
_diffrn_orient_matrix_ub_32      -0.024902
_diffrn_orient_matrix_ub_33      0.055472
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_standards_number         1
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 0 -2

_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_number            2780
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             2654
_reflns_number_gt                2101
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0392P)²+7.2166P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2654
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.866
_refine_diff_density_rms         0.085

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.75887(3) 0.11951(2) 0.72465(3) 0.04167(15) Uani 1 1 d . . .
Cl1 Cl 0.82851(10) 0.08508(10) 0.61725(12) 0.0610(4) Uani 1 1 d . . .
Cl2 Cl 0.78812(11) 0.26020(9) 0.73094(12) 0.0635(4) Uani 1 1 d . . .
Cl3 Cl 0.72368(10) -0.01764(8) 0.73972(12) 0.0592(4) Uani 1 1 d . . .
S1 S 0.61629(9) 0.13298(9) 0.54747(12) 0.0542(4) Uani 1 1 d . . .
O1S O 0.5374(3) 0.1530(3) 0.5614(4) 0.0903(15) Uani 1 1 d . . .
N2 N 0.7146(3) 0.1431(3) 0.8399(4) 0.0499(10) Uani 1 1 d . . .
N1 N 0.7832(3) 0.1341(3) 0.9576(4) 0.0543(11) Uani 1 1 d . . .
N8 N 0.8852(3) 0.1113(2) 0.8931(3) 0.0458(10) Uani 1 1 d . . .
N6 N 0.9407(4) 0.1188(3) 1.1020(4) 0.0769(15) Uani 1 1 d . . .
C5 C 0.7464(5) 0.1464(4) 1.0297(5) 0.0732(18) Uani 1 1 d . . .
H5 H 0.7792 0.1442 1.1132 0.088 Uiso 1 1 calc R . .
C4 C 0.6510(4) 0.1628(4) 0.9512(5) 0.0651(16) Uani 1 1 d . . .
H4 H 0.6062 0.1735 0.9708 0.078 Uiso 1 1 calc R . .
C3 C 0.6360(4) 0.1599(4) 0.8361(5) 0.0623(15) Uani 1 1 d . . .
H3 H 0.5777 0.1687 0.7654 0.075 Uiso 1 1 calc R . .
C7 C 0.8758(4) 0.1200(3) 0.9873(4) 0.0502(12) Uani 1 1 d . . .
C11 C 1.0266(5) 0.1087(4) 1.1240(6) 0.0800(19) Uani 1 1 d . . .
H11 H 1.0766 0.1066 1.204 0.096 Uiso 1 1 calc R . .
C10 C 1.0476(4) 0.1010(3) 1.0374(5) 0.0582(14) Uani 1 1 d . . .
H10 H 1.1097 0.0948 1.0575 0.07 Uiso 1 1 calc R . .
C9 C 0.9738(4) 0.1029(3) 0.9203(5) 0.0535(13) Uani 1 1 d . . .
H9 H 0.9855 0.0983 0.859 0.064 Uiso 1 1 calc R . .
C2S C 0.6181(4) 0.2073(4) 0.4505(5) 0.0773(19) Uani 1 1 d . . .
H2S1 H 0.5563 0.2115 0.3786 0.116 Uiso 1 1 calc R . .
H2S2 H 0.663 0.1911 0.4301 0.116 Uiso 1 1 calc R . .
H2S3 H 0.6361 0.2598 0.4903 0.116 Uiso 1 1 calc R . .
C1S C 0.5845(5) 0.0444(4) 0.4537(5) 0.087(2) Uani 1 1 d . . .
H1S1 H 0.5831 -0.003 0.4964 0.131 Uiso 1 1 calc R . .
H1S2 H 0.6302 0.036 0.4319 0.131 Uiso 1 1 calc R . .
H1S3 H 0.523 0.0525 0.3823 0.131 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N2 2.050(4) . ?
Ru1 N8 2.091(4) . ?
Ru1 S1 2.2824(16) . ?
Ru1 Cl2 2.3272(15) . ?
Ru1 Cl1 2.3309(14) . ?
Ru1 Cl3 2.3380(14) . ?
S1 O1S 1.462(4) . ?
S1 C2S 1.769(5) . ?
S1 C1S 1.780(6) . ?
N2 C3 1.315(6) . ?
N2 N1 1.353(6) . ?
N1 C5 1.395(7) . ?
N1 C7 1.397(7) . ?
N8 C9 1.331(6) . ?
N8 C7 1.339(6) . ?
N6 C7 1.305(7) . ?
N6 C11 1.316(8) . ?
C5 C4 1.384(8) . ?
C4 C3 1.398(7) . ?
C11 C10 1.366(8) . ?
C10 C9 1.364(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
N2 Ru1 N8 77.72(16) . . ?
N2 Ru1 S1 98.34(13) . . ?
N8 Ru1 S1 175.92(11) . . ?
N2 Ru1 Cl2 86.73(12) . . ?
N8 Ru1 Cl2 87.23(11) . . ?
S1 Ru1 Cl2 91.53(5) . . ?
N2 Ru1 Cl1 171.90(12) . . ?
N8 Ru1 Cl1 94.53(11) . . ?
S1 Ru1 Cl1 89.45(6) . . ?
Cl2 Ru1 Cl1 95.34(5) . . ?
N2 Ru1 Cl3 84.70(12) . . ?
N8 Ru1 Cl3 90.34(11) . . ?
S1 Ru1 Cl3 90.32(5) . . ?
Cl2 Ru1 Cl3 171.41(5) . . ?
Cl1 Ru1 Cl3 93.07(6) . . ?
O1S S1 C2S 107.7(3) . . ?
O1S S1 C1S 108.2(3) . . ?
C2S S1 C1S 99.5(3) . . ?
O1S S1 Ru1 114.28(18) . . ?
C2S S1 Ru1 113.0(2) . . ?
C1S S1 Ru1 113.1(2) . . ?
C3 N2 N1 106.4(4) . . ?
C3 N2 Ru1 139.4(4) . . ?
N1 N2 Ru1 114.0(3) . . ?
N2 N1 C5 110.6(4) . . ?
N2 N1 C7 118.0(4) . . ?
C5 N1 C7 131.3(5) . . ?
C9 N8 C7 115.3(4) . . ?
C9 N8 Ru1 129.6(3) . . ?
C7 N8 Ru1 115.0(3) . . ?
C7 N6 C11 112.8(5) . . ?
C4 C5 N1 105.7(5) . . ?
C5 C4 C3 105.5(5) . . ?
N2 C3 C4 111.8(5) . . ?
N6 C7 N8 129.3(5) . . ?
N6 C7 N1 115.8(5) . . ?
N8 C7 N1 114.9(4) . . ?
N6 C11 C10 124.5(6) . . ?
C9 C10 C11 117.4(5) . . ?
N8 C9 C10 120.5(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Ru1 S1 O1S -0.1(3) . . . . ?
N8 Ru1 S1 O1S -14.7(17) . . . . ?
Cl2 Ru1 S1 O1S -87.0(3) . . . . ?
Cl1 Ru1 S1 O1S 177.6(3) . . . . ?
Cl3 Ru1 S1 O1S 84.6(3) . . . . ?
N2 Ru1 S1 C2S 123.5(3) . . . . ?
N8 Ru1 S1 C2S 108.9(16) . . . . ?
Cl2 Ru1 S1 C2S 36.6(3) . . . . ?
Cl1 Ru1 S1 C2S -58.7(3) . . . . ?
Cl3 Ru1 S1 C2S -151.8(3) . . . . ?
N2 Ru1 S1 C1S -124.5(3) . . . . ?
N8 Ru1 S1 C1S -139.1(16) . . . . ?
Cl2 Ru1 S1 C1S 148.6(3) . . . . ?
Cl1 Ru1 S1 C1S 53.3(3) . . . . ?
Cl3 Ru1 S1 C1S -39.8(3) . . . . ?
N8 Ru1 N2 C3 -179.7(6) . . . . ?
S1 Ru1 N2 C3 1.4(6) . . . . ?
Cl2 Ru1 N2 C3 92.5(6) . . . . ?
Cl1 Ru1 N2 C3 -162.5(7) . . . . ?
Cl3 Ru1 N2 C3 -88.2(6) . . . . ?
N8 Ru1 N2 N1 -5.6(3) . . . . ?
S1 Ru1 N2 N1 175.4(3) . . . . ?
Cl2 Ru1 N2 N1 -93.5(3) . . . . ?
Cl1 Ru1 N2 N1 11.6(11) . . . . ?
Cl3 Ru1 N2 N1 85.9(3) . . . . ?
C3 N2 N1 C5 -0.6(6) . . . . ?
Ru1 N2 N1 C5 -176.6(4) . . . . ?
C3 N2 N1 C7 -176.7(5) . . . . ?
Ru1 N2 N1 C7 7.4(6) . . . . ?
N2 Ru1 N8 C9 -172.7(5) . . . . ?
S1 Ru1 N8 C9 -157.9(14) . . . . ?
Cl2 Ru1 N8 C9 -85.5(4) . . . . ?
Cl1 Ru1 N8 C9 9.7(4) . . . . ?
Cl3 Ru1 N8 C9 102.8(4) . . . . ?
N2 Ru1 N8 C7 3.4(4) . . . . ?
S1 Ru1 N8 C7 18.1(18) . . . . ?
Cl2 Ru1 N8 C7 90.6(4) . . . . ?
Cl1 Ru1 N8 C7 -174.2(3) . . . . ?
Cl3 Ru1 N8 C7 -81.1(4) . . . . ?
N2 N1 C5 C4 0.7(6) . . . . ?
C7 N1 C5 C4 176.0(5) . . . . ?
N1 C5 C4 C3 -0.4(7) . . . . ?
N1 N2 C3 C4 0.3(7) . . . . ?
Ru1 N2 C3 C4 174.7(4) . . . . ?
C5 C4 C3 N2 0.1(8) . . . . ?
C11 N6 C7 N8 1.3(9) . . . . ?
C11 N6 C7 N1 -177.4(5) . . . . ?
C9 N8 C7 N6 -2.6(8) . . . . ?
Ru1 N8 C7 N6 -179.3(5) . . . . ?
C9 N8 C7 N1 176.1(4) . . . . ?
Ru1 N8 C7 N1 -0.6(6) . . . . ?
N2 N1 C7 N6 174.4(5) . . . . ?
C5 N1 C7 N6 -0.7(9) . . . . ?
N2 N1 C7 N8 -4.5(7) . . . . ?
C5 N1 C7 N8 -179.6(5) . . . . ?
C7 N6 C11 C10 0.6(10) . . . . ?
N6 C11 C10 C9 -1.0(10) . . . . ?
C7 N8 C9 C10 2.0(7) . . . . ?
Ru1 N8 C9 C10 178.1(4) . . . . ?
C11 C10 C9 N8 -0.5(9) . . . . ?

# END of CIF

_database_code_depnum_ccdc_archive 'CCDC 963268'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_pm176_pna21

_audit_creation_date             2012-06-13T18:36:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H12 Cl3 N4 O1 Ru1 S1'
_chemical_formula_sum            'C9 H12 Cl3 N4 O Ru S'
_chemical_formula_weight         431.71
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_Int_Tables_number      33
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   18.238
_cell_length_b                   7.693
_cell_length_c                   10.678
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1498.2
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      11.3
_cell_measurement_theta_max      18.5
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             852
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.716
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.6411
_exptl_absorpt_correction_T_max  0.6974

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      0.063702
_diffrn_orient_matrix_ub_12      0.018195
_diffrn_orient_matrix_ub_13      0.046603
_diffrn_orient_matrix_ub_21      0.113242
_diffrn_orient_matrix_ub_22      -0.011768
_diffrn_orient_matrix_ub_23      -0.025965
_diffrn_orient_matrix_ub_31      0.001901
_diffrn_orient_matrix_ub_32      0.090946
_diffrn_orient_matrix_ub_33      -0.012591
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_standards_number         1
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
3 -3 -5

_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_number            1391
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             1391
_reflns_number_gt                1309
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0905P)²+0.2826P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1391
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.23(10)
_refine_diff_density_max         1.807
_refine_diff_density_min         -1.684
_refine_diff_density_rms         0.156

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.15012(3) -0.00633(7) 0.35908(11) 0.0302(2) Uani 1 1 d . . .
Cl1 Cl 0.21195(13) -0.2641(3) 0.4015(2) 0.0491(6) Uani 1 1 d . . .
Cl2 Cl 0.07599(12) 0.2329(3) 0.3159(2) 0.0464(5) Uani 1 1 d . . .
Cl3 Cl 0.25776(11) 0.1375(3) 0.3054(2) 0.0457(5) Uani 1 1 d . . .
S1 S 0.16783(12) 0.0784(3) 0.5618(2) 0.0390(5) Uani 1 1 d . . .
O1S O 0.1140(5) 0.0145(8) 0.6542(8) 0.055(2) Uani 1 1 d . . .
N2 N 0.1293(4) -0.0815(9) 0.1744(7) 0.0365(16) Uani 1 1 d . . .
N1 N 0.0709(4) -0.1850(10) 0.1623(6) 0.0391(16) Uani 1 1 d . . .
N8 N 0.0559(4) -0.1645(8) 0.3755(7) 0.0350(15) Uani 1 1 d . . .
N6 N -0.0204(4) -0.3494(11) 0.2536(8) 0.0478(19) Uani 1 1 d . . .
C5 C 0.0562(6) -0.2119(14) 0.0371(9) 0.050(2) Uani 1 1 d . . .
H5 H 0.0186 -0.2799 0.0045 0.059 Uiso 1 1 calc R . .
C4 C 0.1062(5) -0.1216(12) -0.0293(8) 0.045(2) Uani 1 1 d . . .
H4 H 0.1104 -0.1152 -0.116 0.053 Uiso 1 1 calc R . .
C3 C 0.1505(5) -0.0398(15) 0.0595(12) 0.047(2) Uani 1 1 d . . .
H3 H 0.1895 0.0337 0.0407 0.056 Uiso 1 1 calc R . .
C7 C 0.0333(5) -0.2334(11) 0.2677(8) 0.0362(19) Uani 1 1 d . . .
C11 C -0.0561(5) -0.3900(12) 0.3571(12) 0.056(2) Uani 1 1 d . . .
H11 H -0.0956 -0.466 0.3517 0.067 Uiso 1 1 calc R . .
C10 C -0.0372(5) -0.3239(13) 0.4737(10) 0.049(2) Uani 1 1 d . . .
H10 H -0.0629 -0.3559 0.5453 0.059 Uiso 1 1 calc R . .
C9 C 0.0205(5) -0.2100(12) 0.4803(9) 0.043(2) Uani 1 1 d . . .
H9 H 0.035 -0.1647 0.5571 0.051 Uiso 1 1 calc R . .
C2S C 0.2572(7) 0.0177(13) 0.6149(11) 0.056(3) Uani 1 1 d . . .
H2s1 H 0.2676 0.0755 0.6926 0.084 Uiso 1 1 calc R . .
H2s2 H 0.293 0.051 0.5534 0.084 Uiso 1 1 calc R . .
H2s3 H 0.2591 -0.1058 0.6272 0.084 Uiso 1 1 calc R . .
C1S C 0.1722(5) 0.3082(12) 0.5728(11) 0.053(2) Uani 1 1 d . . .
H1s1 H 0.1237 0.3557 0.5662 0.079 Uiso 1 1 calc R . .
H1s2 H 0.2021 0.3528 0.5062 0.079 Uiso 1 1 calc R . .
H1s3 H 0.1932 0.3404 0.6519 0.079 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N2 2.090(7) . ?
Ru1 N8 2.112(7) . ?
Ru1 S1 2.284(3) . ?
Ru1 Cl3 2.325(2) . ?
Ru1 Cl1 2.326(2) . ?
Ru1 Cl2 2.330(2) . ?
S1 O1S 1.476(8) . ?
S1 C1S 1.774(9) . ?
S1 C2S 1.788(12) . ?
N2 C3 1.326(14) . ?
N2 N1 1.336(10) . ?
N1 C7 1.370(12) . ?
N1 C5 1.379(11) . ?
N8 C7 1.332(11) . ?
N8 C9 1.339(12) . ?
N6 C11 1.321(14) . ?
N6 C7 1.332(12) . ?
C5 C4 1.349(15) . ?
C4 C3 1.395(15) . ?
C11 C10 1.388(16) . ?
C10 C9 1.372(13) . ?

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
N2 Ru1 N8 76.7(3) . . ?
N2 Ru1 S1 177.6(2) . . ?
N8 Ru1 S1 101.6(2) . . ?
N2 Ru1 Cl3 93.0(2) . . ?
N8 Ru1 Cl3 168.9(2) . . ?
S1 Ru1 Cl3 88.75(9) . . ?
N2 Ru1 Cl1 92.1(2) . . ?
N8 Ru1 Cl1 83.52(19) . . ?
S1 Ru1 Cl1 89.43(9) . . ?
Cl3 Ru1 Cl1 92.54(9) . . ?
N2 Ru1 Cl2 85.8(2) . . ?
N8 Ru1 Cl2 89.97(19) . . ?
S1 Ru1 Cl2 92.55(9) . . ?
Cl3 Ru1 Cl2 93.74(8) . . ?
Cl1 Ru1 Cl2 173.45(9) . . ?
O1S S1 C1S 108.5(4) . . ?
O1S S1 C2S 108.0(5) . . ?
C1S S1 C2S 101.4(5) . . ?
O1S S1 Ru1 116.4(3) . . ?
C1S S1 Ru1 110.7(4) . . ?
C2S S1 Ru1 110.8(4) . . ?
C3 N2 N1 106.7(7) . . ?
C3 N2 Ru1 138.9(7) . . ?
N1 N2 Ru1 113.7(5) . . ?
N2 N1 C7 118.8(7) . . ?
N2 N1 C5 109.8(8) . . ?
C7 N1 C5 131.2(8) . . ?
C7 N8 C9 117.9(7) . . ?
C7 N8 Ru1 114.2(6) . . ?
C9 N8 Ru1 127.7(6) . . ?
C11 N6 C7 115.2(9) . . ?
C4 C5 N1 107.5(9) . . ?
C5 C4 C3 105.5(8) . . ?
N2 C3 C4 110.5(9) . . ?
N6 C7 N8 126.3(8) . . ?
N6 C7 N1 117.2(8) . . ?
N8 C7 N1 116.5(7) . . ?
N6 C11 C10 122.7(8) . . ?
C9 C10 C11 118.1(9) . . ?
N8 C9 C10 119.6(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Ru1 S1 O1S 44(5) . . . . ?
N8 Ru1 S1 O1S -1.2(4) . . . . ?
Cl3 Ru1 S1 O1S -177.0(4) . . . . ?
Cl1 Ru1 S1 O1S -84.5(4) . . . . ?
Cl2 Ru1 S1 O1S 89.3(4) . . . . ?
N2 Ru1 S1 C1S -80(5) . . . . ?
N8 Ru1 S1 C1S -125.7(4) . . . . ?
Cl3 Ru1 S1 C1S 58.5(4) . . . . ?
Cl1 Ru1 S1 C1S 151.1(4) . . . . ?
Cl2 Ru1 S1 C1S -35.2(4) . . . . ?
N2 Ru1 S1 C2S 168(5) . . . . ?
N8 Ru1 S1 C2S 122.6(4) . . . . ?
Cl3 Ru1 S1 C2S -53.2(4) . . . . ?
Cl1 Ru1 S1 C2S 39.4(4) . . . . ?
Cl2 Ru1 S1 C2S -146.9(4) . . . . ?
N8 Ru1 N2 C3 167.8(10) . . . . ?
S1 Ru1 N2 C3 122(4) . . . . ?
Cl3 Ru1 N2 C3 -16.6(10) . . . . ?
Cl1 Ru1 N2 C3 -109.3(10) . . . . ?
Cl2 Ru1 N2 C3 76.9(10) . . . . ?
N8 Ru1 N2 N1 -0.2(6) . . . . ?
S1 Ru1 N2 N1 -46(5) . . . . ?
Cl3 Ru1 N2 N1 175.3(6) . . . . ?
Cl1 Ru1 N2 N1 82.6(6) . . . . ?
Cl2 Ru1 N2 N1 -91.2(6) . . . . ?
C3 N2 N1 C7 -173.5(8) . . . . ?
Ru1 N2 N1 C7 -1.7(9) . . . . ?
C3 N2 N1 C5 1.3(11) . . . . ?
Ru1 N2 N1 C5 173.2(6) . . . . ?
N2 Ru1 N8 C7 2.0(6) . . . . ?
S1 Ru1 N8 C7 -179.7(5) . . . . ?
Cl3 Ru1 N8 C7 -21.9(14) . . . . ?
Cl1 Ru1 N8 C7 -91.6(6) . . . . ?
Cl2 Ru1 N8 C7 87.7(6) . . . . ?
N2 Ru1 N8 C9 177.6(8) . . . . ?
S1 Ru1 N8 C9 -4.2(8) . . . . ?
Cl3 Ru1 N8 C9 153.7(8) . . . . ?
Cl1 Ru1 N8 C9 83.9(7) . . . . ?
Cl2 Ru1 N8 C9 -96.7(7) . . . . ?
N2 N1 C5 C4 -0.6(11) . . . . ?
C7 N1 C5 C4 173.4(9) . . . . ?
N1 C5 C4 C3 -0.4(11) . . . . ?
N1 N2 C3 C4 -1.6(11) . . . . ?
Ru1 N2 C3 C4 -170.2(7) . . . . ?
C5 C4 C3 N2 1.3(11) . . . . ?
C11 N6 C7 N8 4.1(13) . . . . ?
C11 N6 C7 N1 -178.8(8) . . . . ?
C9 N8 C7 N6 -2.4(13) . . . . ?
Ru1 N8 C7 N6 173.6(7) . . . . ?
C9 N8 C7 N1 -179.6(8) . . . . ?
Ru1 N8 C7 N1 -3.6(9) . . . . ?
N2 N1 C7 N6 -173.9(8) . . . . ?
C5 N1 C7 N6 12.6(14) . . . . ?
N2 N1 C7 N8 3.6(11) . . . . ?
C5 N1 C7 N8 -170.0(9) . . . . ?
C7 N6 C11 C10 -3.1(14) . . . . ?
N6 C11 C10 C9 0.9(16) . . . . ?
C7 N8 C9 C10 -0.2(13) . . . . ?
Ru1 N8 C9 C10 -175.6(7) . . . . ?
C11 C10 C9 N8 0.9(15) . . . . ?

# END of CIF

_database_code_depnum_ccdc_archive 'CCDC 963269'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nC12_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H30 Cl6 Ir2 N8 O3 S2'
_chemical_formula_weight         1091.74

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'
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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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'

_cell_length_a                   11.9417(19)
_cell_length_b                   8.8004(13)
_cell_length_c                   31.028(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.687(6)
_cell_angle_gamma                90.00
_cell_volume                     3259.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7396
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      27.40

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2072
_exptl_absorpt_coefficient_mu    8.816
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2716
_exptl_absorpt_correction_T_max  0.5390
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_suppport 'magnetic support whith MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Micorfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            37339
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_av_sigmaI/netI    0.0865
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         29.95
_reflns_number_total             8465
_reflns_number_gt                6571
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0235P)²+31.9634P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8465
_refine_ls_number_parameters     379
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1091
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Ir1A Ir 0.22880(3) 0.67997(4) 0.172129(9) 0.01537(9) Uani 1 1 d . . .
Ir1B Ir 0.75030(3) 0.22351(4) 0.051211(9) 0.01564(9) Uani 1 1 d . . .
Cl1A Cl 0.38159(18) 0.5296(2) 0.15314(6) 0.0227(4) Uani 1 1 d . . .
Cl2A Cl 0.13024(17) 0.6091(2) 0.10898(6) 0.0212(4) Uani 1 1 d . . .
Cl3A Cl 0.08555(18) 0.8486(2) 0.19225(6) 0.0240(5) Uani 1 1 d . . .
S1A S 0.15131(19) 0.4846(3) 0.20706(6) 0.0216(5) Uani 1 1 d . . .
O1SA O 0.1820(6) 0.4729(8) 0.25330(18) 0.0344(16) Uani 1 1 d . . .
N8A N 0.3041(6) 0.8645(7) 0.1443(2) 0.0190(15) Uani 1 1 d . . .
N6A N 0.4222(7) 1.0751(9) 0.1627(3) 0.0325(19) Uani 1 1 d . . .
N1A N 0.3720(7) 0.8988(9) 0.2137(2) 0.0305(18) Uani 1 1 d . . .
N2A N 0.3217(6) 0.7661(8) 0.2230(2) 0.0199(15) Uani 1 1 d . . .
C9A C 0.2943(7) 0.9123(10) 0.1030(3) 0.0240(19) Uani 1 1 d . . .
H9A H 0.2514 0.8556 0.0823 0.029 Uiso 1 1 calc R . .
C10A C 0.3473(7) 1.0438(10) 0.0912(3) 0.0241(19) Uani 1 1 d . . .
H10A H 0.3412 1.0821 0.0626 0.029 Uiso 1 1 calc R . .
C11A C 0.4093(9) 1.1170(12) 0.1227(3) 0.035(2) Uani 1 1 d . . .
H11A H 0.4465 1.2074 0.1145 0.041 Uiso 1 1 calc R . .
C7A C 0.3664(7) 0.9509(10) 0.1714(3) 0.0243(19) Uani 1 1 d . . .
C3A C 0.4281(8) 0.9541(12) 0.2506(3) 0.033(2) Uani 1 1 d . . .
H3A H 0.4702 1.0455 0.2529 0.039 Uiso 1 1 calc R . .
C4A C 0.4112(7) 0.8534(10) 0.2820(3) 0.025(2) Uani 1 1 d . . .
H4A H 0.4385 0.8592 0.3110 0.030 Uiso 1 1 calc R . .
C5A C 0.3458(7) 0.7387(11) 0.2637(3) 0.027(2) Uani 1 1 d . . .
H5A H 0.3215 0.6513 0.2788 0.033 Uiso 1 1 calc R . .
C1SA C 0.0041(7) 0.4866(11) 0.2020(3) 0.028(2) Uani 1 1 d . . .
H1S1 H -0.0267 0.4041 0.2193 0.042 Uiso 1 1 calc R . .
H1S2 H -0.0188 0.4728 0.1717 0.042 Uiso 1 1 calc R . .
H1S3 H -0.0242 0.5842 0.2124 0.042 Uiso 1 1 calc R . .
C2SA C 0.1812(8) 0.3074(10) 0.1833(3) 0.029(2) Uani 1 1 d . . .
H2S1 H 0.2616 0.2862 0.1866 0.044 Uiso 1 1 calc R . .
H2S2 H 0.1599 0.3104 0.1525 0.044 Uiso 1 1 calc R . .
H2S3 H 0.1388 0.2273 0.1974 0.044 Uiso 1 1 calc R . .
Cl1B Cl 0.65028(19) 0.3587(3) 0.10289(7) 0.0271(5) Uani 1 1 d . . .
Cl3B Cl 0.84699(18) 0.1034(2) -0.00431(6) 0.0211(4) Uani 1 1 d . . .
Cl2B Cl 0.65519(18) -0.0024(2) 0.06654(6) 0.0245(5) Uani 1 1 d . . .
S1B S 0.88613(18) 0.1563(2) 0.09972(6) 0.0191(4) Uani 1 1 d . . .
O1SB O 0.9831(5) 0.2589(7) 0.10407(19) 0.0281(14) Uani 1 1 d . . .
N8B N 0.8116(6) 0.4297(8) 0.0305(2) 0.0190(15) Uani 1 1 d . . .
N6B N 0.7653(7) 0.6256(8) -0.0210(2) 0.0305(18) Uani 1 1 d . . .
N1B N 0.6540(6) 0.4152(8) -0.0155(2) 0.0221(16) Uani 1 1 d . . .
N2B N 0.6300(6) 0.2858(8) 0.0056(2) 0.0209(15) Uani 1 1 d . . .
C9B C 0.9014(8) 0.5089(9) 0.0452(3) 0.0231(19) Uani 1 1 d . . .
H9B H 0.9471 0.4705 0.0683 0.028 Uiso 1 1 calc R . .
C10B C 0.9265(7) 0.6462(9) 0.0263(3) 0.0231(19) Uani 1 1 d U . .
H10B H 0.9906 0.7027 0.0355 0.028 Uiso 1 1 calc R . .
C11B C 0.8558(8) 0.6990(11) -0.0064(3) 0.031(2) Uani 1 1 d . . .
11B H 0.8731 0.7938 -0.0192 0.038 Uiso 1 1 calc R . .
C7B C 0.7483(8) 0.4967(10) -0.0019(3) 0.0224(19) Uani 1 1 d . . .
C3B C 0.5344(7) 0.2336(10) -0.0113(3) 0.0252(19) Uani 1 1 d . . .
H3B H 0.4972 0.1441 -0.0023 0.030 Uiso 1 1 calc R . .
C4B C 0.4964(7) 0.3305(10) -0.0444(3) 0.0241(19) Uani 1 1 d . . .
H4B H 0.4305 0.3171 -0.0619 0.029 Uiso 1 1 calc R . .
C5B C 0.5710(8) 0.4477(10) -0.0472(3) 0.029(2) Uani 1 1 d . . .
H5B H 0.5675 0.5321 -0.0663 0.034 Uiso 1 1 calc R . .
C1SB C 0.9380(8) -0.0290(10) 0.0897(3) 0.027(2) Uani 1 1 d . . .
H1S4 H 0.9850 -0.0267 0.0644 0.041 Uiso 1 1 calc R . .
H1S5 H 0.8750 -0.0985 0.0844 0.041 Uiso 1 1 calc R . .
H1S6 H 0.9825 -0.0639 0.1148 0.041 Uiso 1 1 calc R . .
C2SB C 0.8304(8) 0.1295(11) 0.1518(3) 0.029(2) Uani 1 1 d . . .
H2S4 H 0.8860 0.0779 0.1705 0.043 Uiso 1 1 calc R . .
H2S5 H 0.7624 0.0675 0.1494 0.043 Uiso 1 1 calc R . .
H2S6 H 0.8123 0.2285 0.1643 0.043 Uiso 1 1 calc R . .
O1' O 0.3710(9) 0.2892(13) 0.2873(3) 0.047(2) Uani 0.75 1 d PDU A 1
H1' H 0.3250 0.3543 0.2778 0.071 Uiso 0.75 1 calc PR A 1
C1' C 0.3494(19) 0.257(3) 0.3302(6) 0.0452(14) Uani 0.75 1 d PDU A 1
H2' H 0.3592 0.3516 0.3474 0.054 Uiso 0.75 1 calc PR A 1
H3' H 0.4048 0.1823 0.3413 0.054 Uiso 0.75 1 calc PR A 1
C2' C 0.2368(15) 0.198(2) 0.3363(5) 0.0452(14) Uani 0.75 1 d PDU A 1
H4' H 0.2170 0.2103 0.3665 0.068 Uiso 0.75 1 calc PR A 1
H5' H 0.2346 0.0901 0.3286 0.068 Uiso 0.75 1 calc PR A 1
H6' H 0.1831 0.2540 0.3178 0.068 Uiso 0.75 1 calc PR A 1
O1" O 0.222(2) 0.149(3) 0.3686(9) 0.0452(14) Uani 0.25 1 d PDU B 2
H1" H 0.2779 0.1160 0.3825 0.068 Uiso 0.25 1 calc PR B 2
C1" C 0.250(4) 0.180(6) 0.3263(11) 0.0452(14) Uani 0.25 1 d PDU B 2
H2" H 0.1882 0.2358 0.3117 0.054 Uiso 0.25 1 calc PR B 2
H3" H 0.2606 0.0831 0.3108 0.054 Uiso 0.25 1 calc PR B 2
C2" C 0.353(5) 0.270(10) 0.3237(18) 0.0452(14) Uani 0.25 1 d PDU B 2
H4" H 0.3478 0.3593 0.3424 0.068 Uiso 0.25 1 calc PR B 2
H5" H 0.3622 0.3032 0.2938 0.068 Uiso 0.25 1 calc PR B 2
H6" H 0.4174 0.2081 0.3330 0.068 Uiso 0.25 1 calc PR B 2


_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
Ir1A N2A 2.047(6) . ?
Ir1A N8A 2.058(7) . ?
Ir1A S1A 2.247(2) . ?
Ir1A Cl2A 2.3407(19) . ?
Ir1A Cl1A 2.343(2) . ?
Ir1A Cl3A 2.363(2) . ?
Ir1B N2B 2.060(7) . ?
Ir1B N8B 2.066(7) . ?
Ir1B S1B 2.259(2) . ?
Ir1B Cl2B 2.345(2) . ?
Ir1B Cl1B 2.351(2) . ?
Ir1B Cl3B 2.3527(19) . ?
S1A O1SA 1.474(6) . ?
S1A C1SA 1.760(9) . ?
S1A C2SA 1.766(9) . ?
N8A C7A 1.341(11) . ?
N8A C9A 1.352(10) . ?
N6A C11A 1.300(12) . ?
N6A C7A 1.312(11) . ?
N1A N2A 1.348(10) . ?
N1A C7A 1.390(12) . ?
N1A C3A 1.396(11) . ?
N2A C5A 1.310(11) . ?
C9A C10A 1.373(12) . ?
C10A C11A 1.370(12) . ?
C3A C4A 1.337(13) . ?
C4A C5A 1.387(12) . ?
S1B O1SB 1.472(6) . ?
S1B C1SB 1.774(9) . ?
S1B C2SB 1.782(8) . ?
N8B C9B 1.347(10) . ?
N8B C7B 1.373(10) . ?
N6B C7B 1.298(11) . ?
N6B C11B 1.327(12) . ?
N1B N2B 1.349(9) . ?
N1B C7B 1.390(11) . ?
N1B C5B 1.405(11) . ?
N2B C3B 1.325(11) . ?
C9B C10B 1.380(11) . ?
C10B C11B 1.380(13) . ?
C3B C4B 1.401(12) . ?
C4B C5B 1.367(12) . ?
O1' C1' 1.393(19) . ?
C1' C2' 1.461(16) . ?
O1" C1" 1.393(19) . ?
C1" C2" 1.461(17) . ?

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
N2A Ir1A N8A 78.3(3) . . ?
N2A Ir1A S1A 97.7(2) . . ?
N8A Ir1A S1A 175.9(2) . . ?
N2A Ir1A Cl2A 172.5(2) . . ?
N8A Ir1A Cl2A 94.3(2) . . ?
S1A Ir1A Cl2A 89.75(7) . . ?
N2A Ir1A Cl1A 89.70(19) . . ?
N8A Ir1A Cl1A 89.3(2) . . ?
S1A Ir1A Cl1A 91.36(8) . . ?
Cl2A Ir1A Cl1A 90.86(7) . . ?
N2A Ir1A Cl3A 86.78(19) . . ?
N8A Ir1A Cl3A 86.8(2) . . ?
S1A Ir1A Cl3A 92.39(8) . . ?
Cl2A Ir1A Cl3A 92.21(7) . . ?
Cl1A Ir1A Cl3A 175.17(8) . . ?
N2B Ir1B N8B 78.4(3) . . ?
N2B Ir1B S1B 178.3(2) . . ?
N8B Ir1B S1B 100.6(2) . . ?
N2B Ir1B Cl2B 91.9(2) . . ?
N8B Ir1B Cl2B 170.3(2) . . ?
S1B Ir1B Cl2B 89.16(7) . . ?
N2B Ir1B Cl1B 88.59(19) . . ?
N8B Ir1B Cl1B 87.67(19) . . ?
S1B Ir1B Cl1B 92.72(8) . . ?
Cl2B Ir1B Cl1B 91.83(8) . . ?
N2B Ir1B Cl3B 87.95(19) . . ?
N8B Ir1B Cl3B 88.90(18) . . ?
S1B Ir1B Cl3B 90.68(7) . . ?
Cl2B Ir1B Cl3B 91.07(7) . . ?
Cl1B Ir1B Cl3B 175.56(7) . . ?
O1SA S1A C1SA 107.8(4) . . ?
O1SA S1A C2SA 107.3(4) . . ?
C1SA S1A C2SA 100.7(5) . . ?
O1SA S1A Ir1A 115.4(3) . . ?
C1SA S1A Ir1A 111.9(3) . . ?
C2SA S1A Ir1A 112.5(3) . . ?
C7A N8A C9A 116.6(7) . . ?
C7A N8A Ir1A 115.2(6) . . ?
C9A N8A Ir1A 128.0(6) . . ?
C11A N6A C7A 112.6(9) . . ?
N2A N1A C7A 118.5(7) . . ?
N2A N1A C3A 109.5(7) . . ?
C7A N1A C3A 131.9(8) . . ?
C5A N2A N1A 106.2(7) . . ?
C5A N2A Ir1A 140.7(7) . . ?
N1A N2A Ir1A 113.1(5) . . ?
N8A C9A C10A 119.1(8) . . ?
C11A C10A C9A 116.7(8) . . ?
N6A C11A C10A 126.5(10) . . ?
N6A C7A N8A 128.3(9) . . ?
N6A C7A N1A 117.2(8) . . ?
N8A C7A N1A 114.5(8) . . ?
C4A C3A N1A 106.7(9) . . ?
C3A C4A C5A 106.2(8) . . ?
N2A C5A C4A 111.4(8) . . ?
O1SB S1B C1SB 107.6(4) . . ?
O1SB S1B C2SB 108.1(4) . . ?
C1SB S1B C2SB 100.3(4) . . ?
O1SB S1B Ir1B 116.6(3) . . ?
C1SB S1B Ir1B 111.8(3) . . ?
C2SB S1B Ir1B 111.1(3) . . ?
C9B N8B C7B 116.2(7) . . ?
C9B N8B Ir1B 129.4(6) . . ?
C7B N8B Ir1B 114.4(6) . . ?
C7B N6B C11B 114.0(9) . . ?
N2B N1B C7B 118.1(7) . . ?
N2B N1B C5B 110.9(7) . . ?
C7B N1B C5B 131.0(7) . . ?
C3B N2B N1B 107.1(7) . . ?
C3B N2B Ir1B 139.0(6) . . ?
N1B N2B Ir1B 113.8(5) . . ?
N8B C9B C10B 119.3(8) . . ?
C9B C10B C11B 118.1(8) . . ?
N6B C11B C10B 124.1(9) . . ?
N6B C7B N8B 128.3(9) . . ?
N6B C7B N1B 116.7(8) . . ?
N8B C7B N1B 115.1(7) . . ?
N2B C3B C4B 109.6(8) . . ?
C5B C4B C3B 108.0(8) . . ?
C4B C5B N1B 104.4(8) . . ?
O1' C1' C2' 113.1(14) . . ?
O1" C1" C2" 113.0(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2A Ir1A S1A O1SA 1.5(4) . . . . ?
Cl2A Ir1A S1A O1SA -177.7(3) . . . . ?
Cl1A Ir1A S1A O1SA 91.4(3) . . . . ?
Cl3A Ir1A S1A O1SA -85.5(3) . . . . ?
N2A Ir1A S1A C1SA 125.3(4) . . . . ?
Cl2A Ir1A S1A C1SA -53.9(3) . . . . ?
Cl1A Ir1A S1A C1SA -144.8(3) . . . . ?
Cl3A Ir1A S1A C1SA 38.3(3) . . . . ?
N2A Ir1A S1A C2SA -122.1(4) . . . . ?
N8A Ir1A S1A C2SA -131(3) . . . . ?
Cl2A Ir1A S1A C2SA 58.6(4) . . . . ?
Cl1A Ir1A S1A C2SA -32.2(4) . . . . ?
Cl3A Ir1A S1A C2SA 150.8(4) . . . . ?
N2A Ir1A N8A C7A -4.1(6) . . . . ?
Cl2A Ir1A N8A C7A 175.3(6) . . . . ?
Cl1A Ir1A N8A C7A -93.9(6) . . . . ?
Cl3A Ir1A N8A C7A 83.3(6) . . . . ?
N2A Ir1A N8A C9A 179.2(8) . . . . ?
Cl2A Ir1A N8A C9A -1.4(7) . . . . ?
Cl1A Ir1A N8A C9A 89.4(7) . . . . ?
Cl3A Ir1A N8A C9A -93.4(7) . . . . ?
C7A N1A N2A C5A 175.8(8) . . . . ?
C3A N1A N2A C5A -0.4(10) . . . . ?
C7A N1A N2A Ir1A -7.1(9) . . . . ?
C3A N1A N2A Ir1A 176.7(6) . . . . ?
N8A Ir1A N2A C5A -178.6(10) . . . . ?
S1A Ir1A N2A C5A 2.1(10) . . . . ?
Cl1A Ir1A N2A C5A -89.3(9) . . . . ?
Cl3A Ir1A N2A C5A 94.1(9) . . . . ?
N8A Ir1A N2A N1A 5.8(5) . . . . ?
S1A Ir1A N2A N1A -173.5(5) . . . . ?
Cl1A Ir1A N2A N1A 95.1(5) . . . . ?
Cl3A Ir1A N2A N1A -81.5(5) . . . . ?
C7A N8A C9A C10A -0.1(12) . . . . ?
Ir1A N8A C9A C10A 176.6(6) . . . . ?
N8A C9A C10A C11A 1.2(13) . . . . ?
C7A N6A C11A C10A -1.1(15) . . . . ?
C9A C10A C11A N6A -0.6(15) . . . . ?
C11A N6A C7A N8A 2.6(14) . . . . ?
C11A N6A C7A N1A -178.2(8) . . . . ?
C9A N8A C7A N6A -2.0(13) . . . . ?
Ir1A N8A C7A N6A -179.1(8) . . . . ?
C9A N8A C7A N1A 178.7(7) . . . . ?
Ir1A N8A C7A N1A 1.6(9) . . . . ?
N2A N1A C7A N6A -175.6(8) . . . . ?
C3A N1A C7A N6A -0.4(15) . . . . ?
N2A N1A C7A N8A 3.7(11) . . . . ?
C3A N1A C7A N8A 178.9(9) . . . . ?
N2A N1A C3A C4A 0.1(10) . . . . ?
C7A N1A C3A C4A -175.5(9) . . . . ?
N1A C3A C4A C5A 0.3(11) . . . . ?
N1A N2A C5A C4A 0.6(10) . . . . ?
Ir1A N2A C5A C4A -175.2(7) . . . . ?
C3A C4A C5A N2A -0.6(11) . . . . ?
N8B Ir1B S1B O1SB -3.1(4) . . . . ?
Cl2B Ir1B S1B O1SB 176.9(3) . . . . ?
Cl1B Ir1B S1B O1SB -91.3(3) . . . . ?
Cl3B Ir1B S1B O1SB 85.9(3) . . . . ?
N8B Ir1B S1B C1SB -127.5(4) . . . . ?
Cl2B Ir1B S1B C1SB 52.6(3) . . . . ?
Cl1B Ir1B S1B C1SB 144.4(3) . . . . ?
Cl3B Ir1B S1B C1SB -38.5(3) . . . . ?
N8B Ir1B S1B C2SB 121.4(4) . . . . ?
Cl2B Ir1B S1B C2SB -58.6(3) . . . . ?
Cl1B Ir1B S1B C2SB 33.2(3) . . . . ?
Cl3B Ir1B S1B C2SB -149.6(3) . . . . ?
N2B Ir1B N8B C9B 175.3(7) . . . . ?
S1B Ir1B N8B C9B -6.1(7) . . . . ?
Cl1B Ir1B N8B C9B 86.2(7) . . . . ?
Cl3B Ir1B N8B C9B -96.6(7) . . . . ?
N2B Ir1B N8B C7B -2.2(5) . . . . ?
S1B Ir1B N8B C7B 176.5(5) . . . . ?
Cl1B Ir1B N8B C7B -91.2(5) . . . . ?
Cl3B Ir1B N8B C7B 86.0(5) . . . . ?
C7B N1B N2B C3B 176.6(7) . . . . ?
C5B N1B N2B C3B -0.1(9) . . . . ?
C7B N1B N2B Ir1B -5.7(9) . . . . ?
C5B N1B N2B Ir1B 177.6(5) . . . . ?
N8B Ir1B N2B C3B -179.2(9) . . . . ?
Cl2B Ir1B N2B C3B 0.5(9) . . . . ?
Cl1B Ir1B N2B C3B -91.3(9) . . . . ?
Cl3B Ir1B N2B C3B 91.5(9) . . . . ?
N8B Ir1B N2B N1B 4.1(5) . . . . ?
Cl2B Ir1B N2B N1B -176.2(5) . . . . ?
Cl1B Ir1B N2B N1B 92.0(5) . . . . ?
Cl3B Ir1B N2B N1B -85.2(5) . . . . ?
C7B N8B C9B C10B -2.4(11) . . . . ?
Ir1B N8B C9B C10B -179.7(6) . . . . ?
N8B C9B C10B C11B 1.8(12) . . . . ?
C7B N6B C11B C10B -0.4(13) . . . . ?
C9B C10B C11B N6B -0.3(14) . . . . ?
C11B N6B C7B N8B -0.2(13) . . . . ?
C11B N6B C7B N1B 179.3(7) . . . . ?
C9B N8B C7B N6B 1.7(12) . . . . ?
Ir1B N8B C7B N6B 179.4(7) . . . . ?
C9B N8B C7B N1B -177.9(7) . . . . ?
Ir1B N8B C7B N1B -0.1(9) . . . . ?
N2B N1B C7B N6B -175.7(7) . . . . ?
C5B N1B C7B N6B 0.2(13) . . . . ?
N2B N1B C7B N8B 3.9(10) . . . . ?
C5B N1B C7B N8B 179.8(8) . . . . ?
N1B N2B C3B C4B 0.8(9) . . . . ?
Ir1B N2B C3B C4B -176.0(6) . . . . ?
N2B C3B C4B C5B -1.2(10) . . . . ?
C3B C4B C5B N1B 1.0(9) . . . . ?
N2B N1B C5B C4B -0.6(9) . . . . ?
C7B N1B C5B C4B -176.8(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.894
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.969
_refine_diff_density_min         -3.167
_refine_diff_density_rms         0.282
_database_code_depnum_ccdc_archive 'CCDC 963270'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nC5_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H12 Cl3 Ir N4 O S'
_chemical_formula_weight         522.84

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'
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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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'

_cell_length_a                   6.7900(5)
_cell_length_b                   8.0111(5)
_cell_length_c                   26.8108(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.555(2)
_cell_angle_gamma                90.00
_cell_volume                     1458.32(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      29.65

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    9.844
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0837
_exptl_absorpt_correction_T_max  0.3198
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_suppport 'magnetic support whith MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Micorfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            18001
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         29.85
_reflns_number_total             3834
_reflns_number_gt                3459
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0575P)²+10.7760P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3834
_refine_ls_number_parameters     257
_refine_ls_number_restraints     436
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Ir1 Ir 0.30529(3) 0.97160(3) 0.143788(9) 0.00821(10) Uani 1 1 d . . .
Cl1 Cl 0.5345(2) 0.80313(19) 0.18609(6) 0.0139(3) Uani 1 1 d . A .
Cl2 Cl 0.1334(2) 1.0143(2) 0.21833(6) 0.0149(3) Uani 1 1 d . A .
Cl3 Cl 0.0692(2) 1.12281(18) 0.09686(6) 0.0111(3) Uani 1 1 d . A .
S1 S 0.4733(2) 1.21139(19) 0.15478(6) 0.0108(3) Uani 1 1 d . A .
O1S O 0.5516(7) 1.2825(6) 0.10815(19) 0.0189(11) Uani 1 1 d . . .
N8 N 0.437(4) 0.893(4) 0.0809(11) 0.0120(12) Uani 0.55 1 d PDU A 1
C9 C 0.615(3) 0.945(2) 0.0630(6) 0.0121(13) Uani 0.55 1 d PDU A 1
H9 H 0.6862 1.0336 0.0783 0.015 Uiso 0.55 1 calc PR A 1
C10 C 0.6886(17) 0.8622(14) 0.0215(4) 0.0114(13) Uani 0.55 1 d PDU A 1
H10 H 0.8114 0.8946 0.0079 0.014 Uiso 0.55 1 calc PR A 1
C11 C 0.5831(16) 0.7333(14) 0.0001(4) 0.0133(13) Uani 0.55 1 d PDU A 1
H11 H 0.6329 0.6817 -0.0290 0.016 Uiso 0.55 1 calc PR A 1
N6 N 0.4111(15) 0.6775(13) 0.0192(4) 0.0140(13) Uani 0.55 1 d PDU A 1
C7 C 0.347(3) 0.756(3) 0.0583(9) 0.0133(11) Uani 0.55 1 d PDU A 1
N1 N 0.185(2) 0.696(2) 0.0837(5) 0.0131(8) Uani 0.55 1 d PDU A 1
N2 N 0.142(3) 0.761(3) 0.1277(6) 0.0112(9) Uani 0.55 1 d PDU A 1
C3 C -0.018(5) 0.686(4) 0.1426(10) 0.0132(12) Uani 0.55 1 d PDU A 1
H3 H -0.0868 0.7109 0.1724 0.016 Uiso 0.55 1 calc PR A 1
C4 C -0.0744(18) 0.5613(16) 0.1077(5) 0.0148(13) Uani 0.55 1 d PDU A 1
H4 H -0.1812 0.4852 0.1101 0.018 Uiso 0.55 1 calc PR A 1
C5 C 0.0538(17) 0.5737(15) 0.0708(5) 0.0155(12) Uani 0.55 1 d PDU A 1
H5 H 0.0546 0.5093 0.0411 0.019 Uiso 0.55 1 calc PR A 1
N8' N 0.143(4) 0.763(3) 0.1211(7) 0.0112(9) Uani 0.45 1 d PDU A 2
C9' C -0.015(6) 0.695(5) 0.1450(12) 0.0129(12) Uani 0.45 1 d PDU A 2
H9' H -0.0517 0.7311 0.1774 0.015 Uiso 0.45 1 calc PR A 2
C10' C -0.121(2) 0.5714(19) 0.1202(5) 0.0137(14) Uani 0.45 1 d PDU A 2
H10' H -0.2356 0.5253 0.1348 0.016 Uiso 0.45 1 calc PR A 2
C11' C -0.0591(19) 0.5156(16) 0.0743(5) 0.0163(14) Uani 0.45 1 d PDU A 2
H11' H -0.1300 0.4279 0.0584 0.020 Uiso 0.45 1 calc PR A 2
N6' N 0.0994(17) 0.5814(15) 0.0509(4) 0.0151(13) Uani 0.45 1 d PDU A 2
C7' C 0.198(3) 0.694(3) 0.0757(7) 0.0131(8) Uani 0.45 1 d PDU A 2
N1' N 0.363(3) 0.768(3) 0.0552(8) 0.0133(11) Uani 0.45 1 d PDU A 2
N2' N 0.446(5) 0.896(4) 0.0781(13) 0.0121(12) Uani 0.45 1 d PDU A 2
C3' C 0.611(3) 0.926(3) 0.0546(7) 0.0125(13) Uani 0.45 1 d PDU A 2
H3' H 0.7058 1.0076 0.0643 0.015 Uiso 0.45 1 calc PR A 2
C4' C 0.6259(19) 0.8199(18) 0.0126(5) 0.0135(13) Uani 0.45 1 d PDU A 2
H4' H 0.7273 0.8191 -0.0115 0.016 Uiso 0.45 1 calc PR A 2
C5' C 0.469(2) 0.7217(17) 0.0141(5) 0.0140(13) Uani 0.45 1 d PDU A 2
H5' H 0.4355 0.6358 -0.0089 0.017 Uiso 0.45 1 calc PR A 2
C1S C 0.6707(8) 1.1907(7) 0.1980(2) 0.0170(14) Uani 1 1 d . . .
H1s1 H 0.7730 1.1194 0.1837 0.026 Uiso 1 1 calc R A .
H1s2 H 0.6225 1.1401 0.2288 0.026 Uiso 1 1 calc R . .
H1s3 H 0.7260 1.3011 0.2053 0.026 Uiso 1 1 calc R . .
C2S C 0.3225(8) 1.3665(7) 0.1829(2) 0.0181(14) Uani 1 1 d R . .
H2s1 H 0.3954 1.4712 0.1851 0.027 Uiso 1 1 d R . .
H2s2 H 0.2851 1.3303 0.2166 0.027 Uiso 1 1 d R . .
H2s3 H 0.2034 1.3826 0.1626 0.027 Uiso 1 1 d 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
Ir1 N8 2.02(2) . ?
Ir1 N2 2.06(2) . ?
Ir1 N8' 2.09(2) . ?
Ir1 N2' 2.10(2) . ?
Ir1 S1 2.2521(15) . ?
Ir1 Cl1 2.3444(16) . ?
Ir1 Cl2 2.3493(16) . ?
Ir1 Cl3 2.3626(16) . ?
S1 O1S 1.478(5) . ?
S1 C1S 1.771(6) . ?
S1 C2S 1.782(5) . ?
N8 C9 1.37(3) . ?
N8 C7 1.39(2) . ?
C9 C10 1.389(16) . ?
C10 C11 1.379(14) . ?
C11 N6 1.355(12) . ?
N6 C7 1.30(2) . ?
C7 N1 1.384(10) . ?
N1 N2 1.32(2) . ?
N1 C5 1.368(18) . ?
N2 C3 1.31(3) . ?
C3 C4 1.417(16) . ?
C4 C5 1.327(15) . ?
N8' C9' 1.37(3) . ?
N8' C7' 1.39(2) . ?
C9' C10' 1.389(17) . ?
C10' C11' 1.379(14) . ?
C11' N6' 1.357(12) . ?
N6' C7' 1.30(2) . ?
C7' N1' 1.384(10) . ?
N1' N2' 1.32(2) . ?
N1' C5' 1.369(18) . ?
N2' C3' 1.31(3) . ?
C3' C4' 1.417(16) . ?
C4' C5' 1.328(15) . ?

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
N8 Ir1 N2 79.1(3) . . ?
N8 Ir1 N8' 75.1(10) . . ?
N2 Ir1 N8' 4.9(10) . . ?
N8 Ir1 N2' 1.6(12) . . ?
N2 Ir1 N2' 80.6(10) . . ?
N8' Ir1 N2' 76.6(3) . . ?
N8 Ir1 S1 98.5(5) . . ?
N2 Ir1 S1 174.8(6) . . ?
N8' Ir1 S1 170.2(6) . . ?
N2' Ir1 S1 97.0(6) . . ?
N8 Ir1 Cl1 85.8(12) . . ?
N2 Ir1 Cl1 89.0(7) . . ?
N8' Ir1 Cl1 91.5(9) . . ?
N2' Ir1 Cl1 86.2(14) . . ?
S1 Ir1 Cl1 95.43(6) . . ?
N8 Ir1 Cl2 169.9(7) . . ?
N2 Ir1 Cl2 91.6(5) . . ?
N8' Ir1 Cl2 95.7(5) . . ?
N2' Ir1 Cl2 171.5(8) . . ?
S1 Ir1 Cl2 91.13(6) . . ?
Cl1 Ir1 Cl2 90.30(6) . . ?
N8 Ir1 Cl3 91.1(12) . . ?
N2 Ir1 Cl3 87.0(7) . . ?
N8' Ir1 Cl3 84.3(9) . . ?
N2' Ir1 Cl3 90.8(14) . . ?
S1 Ir1 Cl3 88.43(6) . . ?
Cl1 Ir1 Cl3 175.37(6) . . ?
Cl2 Ir1 Cl3 92.19(6) . . ?
O1S S1 C1S 108.3(3) . . ?
O1S S1 C2S 107.6(3) . . ?
C1S S1 C2S 102.9(3) . . ?
O1S S1 Ir1 113.8(2) . . ?
C1S S1 Ir1 112.6(2) . . ?
C2S S1 Ir1 111.0(2) . . ?
C9 N8 C7 118.2(17) . . ?
C9 N8 Ir1 126.8(14) . . ?
C7 N8 Ir1 114.4(12) . . ?
N8 C9 C10 117.4(15) . . ?
C11 C10 C9 120.1(12) . . ?
N6 C11 C10 122.4(9) . . ?
C7 N6 C11 116.2(10) . . ?
N6 C7 N1 120.3(15) . . ?
N6 C7 N8 125.5(14) . . ?
N1 C7 N8 114.0(18) . . ?
N2 N1 C5 111.0(12) . . ?
N2 N1 C7 119.1(18) . . ?
C5 N1 C7 129.9(16) . . ?
C3 N2 N1 106.5(16) . . ?
C3 N2 Ir1 139.3(16) . . ?
N1 N2 Ir1 112.6(11) . . ?
N2 C3 C4 109.8(16) . . ?
C5 C4 C3 105.4(12) . . ?
C4 C5 N1 107.2(10) . . ?
C9' N8' C7' 118.1(17) . . ?
C9' N8' Ir1 126.5(14) . . ?
C7' N8' Ir1 115.3(13) . . ?
N8' C9' C10' 117.5(16) . . ?
C11' C10' C9' 120.0(12) . . ?
N6' C11' C10' 122.4(10) . . ?
C7' N6' C11' 116.2(11) . . ?
N6' C7' N1' 120.5(16) . . ?
N6' C7' N8' 125.3(15) . . ?
N1' C7' N8' 113.8(19) . . ?
N2' N1' C5' 111.1(13) . . ?
N2' N1' C7' 119.3(19) . . ?
C5' N1' C7' 129.4(17) . . ?
C3' N2' N1' 106.5(17) . . ?
C3' N2' Ir1 138.2(16) . . ?
N1' N2' Ir1 114.8(13) . . ?
N2' C3' C4' 109.7(16) . . ?
C5' C4' C3' 105.6(12) . . ?
C4' C5' N1' 106.9(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N8 Ir1 S1 O1S 26.1(12) . . . . ?
N2' Ir1 S1 O1S 25.8(14) . . . . ?
Cl1 Ir1 S1 O1S 112.6(2) . . . . ?
Cl2 Ir1 S1 O1S -157.0(2) . . . . ?
Cl3 Ir1 S1 O1S -64.8(2) . . . . ?
N8 Ir1 S1 C1S -97.6(12) . . . . ?
N2' Ir1 S1 C1S -97.9(14) . . . . ?
Cl1 Ir1 S1 C1S -11.1(2) . . . . ?
Cl2 Ir1 S1 C1S 79.3(2) . . . . ?
Cl3 Ir1 S1 C1S 171.5(2) . . . . ?
N8 Ir1 S1 C2S 147.7(12) . . . . ?
N2' Ir1 S1 C2S 147.3(14) . . . . ?
Cl1 Ir1 S1 C2S -125.8(2) . . . . ?
Cl2 Ir1 S1 C2S -35.4(2) . . . . ?
Cl3 Ir1 S1 C2S 56.8(2) . . . . ?
N2 Ir1 N8 C9 -166(3) . . . . ?
S1 Ir1 N8 C9 19(3) . . . . ?
Cl1 Ir1 N8 C9 -76(3) . . . . ?
Cl2 Ir1 N8 C9 -143(4) . . . . ?
Cl3 Ir1 N8 C9 108(3) . . . . ?
N2 Ir1 N8 C7 5(2) . . . . ?
S1 Ir1 N8 C7 -170(2) . . . . ?
Cl1 Ir1 N8 C7 95(2) . . . . ?
Cl2 Ir1 N8 C7 27(8) . . . . ?
Cl3 Ir1 N8 C7 -82(2) . . . . ?
C7 N8 C9 C10 3(4) . . . . ?
Ir1 N8 C9 C10 174(2) . . . . ?
N8 C9 C10 C11 0(3) . . . . ?
C9 C10 C11 N6 -3(2) . . . . ?
C10 C11 N6 C7 2(2) . . . . ?
C11 N6 C7 N1 -172.7(18) . . . . ?
C11 N6 C7 N8 2(3) . . . . ?
C9 N8 C7 N6 -4(4) . . . . ?
Ir1 N8 C7 N6 -176(2) . . . . ?
C9 N8 C7 N1 170(3) . . . . ?
Ir1 N8 C7 N1 -1(3) . . . . ?
N6 C7 N1 N2 169(2) . . . . ?
N8 C7 N1 N2 -6(3) . . . . ?
N6 C7 N1 C5 -10(4) . . . . ?
N8 C7 N1 C5 175(2) . . . . ?
C5 N1 N2 C3 -2(3) . . . . ?
C7 N1 N2 C3 179(3) . . . . ?
C5 N1 N2 Ir1 -170.5(14) . . . . ?
C7 N1 N2 Ir1 10(3) . . . . ?
N8 Ir1 N2 C3 -171(4) . . . . ?
Cl1 Ir1 N2 C3 103(4) . . . . ?
Cl2 Ir1 N2 C3 13(4) . . . . ?
Cl3 Ir1 N2 C3 -79(4) . . . . ?
N8 Ir1 N2 N1 -8.1(19) . . . . ?
Cl1 Ir1 N2 N1 -94.0(16) . . . . ?
Cl2 Ir1 N2 N1 175.7(16) . . . . ?
Cl3 Ir1 N2 N1 83.6(16) . . . . ?
N1 N2 C3 C4 3(4) . . . . ?
Ir1 N2 C3 C4 167(2) . . . . ?
N2 C3 C4 C5 -3(4) . . . . ?
C3 C4 C5 N1 2(3) . . . . ?
N2 N1 C5 C4 0(2) . . . . ?
C7 N1 C5 C4 179(2) . . . . ?
N2' Ir1 N8' C9' 179(4) . . . . ?
Cl1 Ir1 N8' C9' 93(4) . . . . ?
Cl2 Ir1 N8' C9' 3(4) . . . . ?
Cl3 Ir1 N8' C9' -89(4) . . . . ?
N2' Ir1 N8' C7' -4(2) . . . . ?
Cl1 Ir1 N8' C7' -90(2) . . . . ?
Cl2 Ir1 N8' C7' 180(2) . . . . ?
Cl3 Ir1 N8' C7' 88(2) . . . . ?
C7' N8' C9' C10' -6(6) . . . . ?
Ir1 N8' C9' C10' 171(3) . . . . ?
N8' C9' C10' C11' 3(6) . . . . ?
C9' C10' C11' N6' -2(4) . . . . ?
C10' C11' N6' C7' 4(3) . . . . ?
C11' N6' C7' N1' 180(2) . . . . ?
C11' N6' C7' N8' -7(3) . . . . ?
C9' N8' C7' N6' 8(5) . . . . ?
Ir1 N8' C7' N6' -169(2) . . . . ?
C9' N8' C7' N1' -178(4) . . . . ?
Ir1 N8' C7' N1' 5(3) . . . . ?
N6' C7' N1' N2' 171(3) . . . . ?
N8' C7' N1' N2' -2(4) . . . . ?
N6' C7' N1' C5' -13(4) . . . . ?
N8' C7' N1' C5' 173(3) . . . . ?
C5' N1' N2' C3' -4(4) . . . . ?
C7' N1' N2' C3' 172(3) . . . . ?
C5' N1' N2' Ir1 -177(2) . . . . ?
C7' N1' N2' Ir1 -1(4) . . . . ?
N8' Ir1 N2' C3' -167(5) . . . . ?
S1 Ir1 N2' C3' 20(5) . . . . ?
Cl1 Ir1 N2' C3' -75(5) . . . . ?
Cl3 Ir1 N2' C3' 109(5) . . . . ?
N8' Ir1 N2' N1' 3(3) . . . . ?
S1 Ir1 N2' N1' -170(3) . . . . ?
Cl1 Ir1 N2' N1' 95(3) . . . . ?
Cl3 Ir1 N2' N1' -81(3) . . . . ?
N1' N2' C3' C4' 4(4) . . . . ?
Ir1 N2' C3' C4' 175(4) . . . . ?
N2' C3' C4' C5' -3(3) . . . . ?
C3' C4' C5' N1' 0(2) . . . . ?
N2' N1' C5' C4' 2(3) . . . . ?
C7' N1' C5' C4' -173(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.911
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         3.413
_refine_diff_density_min         -3.303
_refine_diff_density_rms         0.367
_database_code_depnum_ccdc_archive 'CCDC 963271'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_pm156

_audit_creation_date             2011-02-09T10:52:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C11 H18 Cl2 N4 O2 Ru1 S2'
_chemical_formula_sum            'C11 H18 Cl2 N4 O2 Ru S2'
_chemical_formula_weight         474.38
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   9.575(3)
_cell_length_b                   18.929(5)
_cell_length_c                   9.702(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.19(2)
_cell_angle_gamma                90
_cell_volume                     1758.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      11.3
_cell_measurement_theta_max      18.5
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.443
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.6478
_exptl_absorpt_correction_T_max  0.7073

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      0.037532
_diffrn_orient_matrix_ub_12      -0.048904
_diffrn_orient_matrix_ub_13      -0.01096
_diffrn_orient_matrix_ub_21      0.069545
_diffrn_orient_matrix_ub_22      0.009003
_diffrn_orient_matrix_ub_23      0.076283
_diffrn_orient_matrix_ub_31      -0.068266
_diffrn_orient_matrix_ub_32      -0.017757
_diffrn_orient_matrix_ub_33      0.068407
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_standards_number         2
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
5 5 3
5 3 2

_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_number            4220
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_full        27.97
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             4220
_reflns_number_gt                3146
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0254P)²+4.3705P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4220
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0932
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.109

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.76926(4) 0.134465(19) 0.25830(4) 0.03178(10) Uani 1 1 d . . .
Cl1 Cl 0.67677(14) 0.01588(7) 0.25688(13) 0.0470(3) Uani 1 1 d . . .
Cl2 Cl 0.87721(13) 0.24887(7) 0.25366(12) 0.0449(3) Uani 1 1 d . . .
S1 S 0.68854(13) 0.15105(7) 0.03756(12) 0.0384(3) Uani 1 1 d . . .
S2 S 0.57070(14) 0.17724(8) 0.34727(14) 0.0485(3) Uani 1 1 d . . .
O1S O 0.7839(4) 0.1276(2) -0.0726(3) 0.0623(11) Uani 1 1 d . . .
O2S O 0.4524(4) 0.1957(3) 0.2557(5) 0.0749(13) Uani 1 1 d . . .
N2 N 0.8681(4) 0.1174(2) 0.4529(4) 0.0395(9) Uani 1 1 d . . .
N1 N 1.0007(4) 0.0921(2) 0.4436(4) 0.0398(9) Uani 1 1 d . . .
N8 N 0.9709(4) 0.0924(2) 0.2067(4) 0.0363(8) Uani 1 1 d . . .
N6 N 1.1854(4) 0.0556(2) 0.3157(5) 0.0498(11) Uani 1 1 d . . .
C5 C 1.0640(6) 0.0842(3) 0.5719(5) 0.0532(14) Uani 1 1 d . . .
H5 H 1.1537 0.0676 0.5915 0.064 Uiso 1 1 calc R . .
C4 C 0.9663(7) 0.1058(3) 0.6640(5) 0.0568(15) Uani 1 1 d . . .
H4 H 0.9767 0.1068 0.7595 0.068 Uiso 1 1 calc R . .
C3 C 0.8494(6) 0.1259(3) 0.5880(5) 0.0525(14) Uani 1 1 d . . .
H3 H 0.7678 0.1431 0.6261 0.063 Uiso 1 1 calc R . .
C7 C 1.0569(5) 0.0796(2) 0.3150(5) 0.0372(10) Uani 1 1 d . . .
C11 C 1.2362(6) 0.0436(3) 0.1920(6) 0.0552(14) Uani 1 1 d . . .
H11 H 1.3272 0.027 0.1861 0.066 Uiso 1 1 calc R . .
C10 C 1.1619(5) 0.0545(3) 0.0737(6) 0.0503(13) Uani 1 1 d . . .
H10 H 1.2009 0.0455 -0.0115 0.06 Uiso 1 1 calc R . .
C9 C 1.0280(5) 0.0790(3) 0.0828(5) 0.0452(12) Uani 1 1 d . . .
H9 H 0.9753 0.0865 0.0026 0.054 Uiso 1 1 calc R . .
C2S C 0.5251(6) 0.1113(3) -0.0022(6) 0.0574(15) Uani 1 1 d . . .
H2s1 H 0.5023 0.1185 -0.098 0.086 Uiso 1 1 calc R . .
H2s2 H 0.4543 0.1323 0.0531 0.086 Uiso 1 1 calc R . .
H2s3 H 0.5303 0.0616 0.0166 0.086 Uiso 1 1 calc R . .
C1S C 0.6482(6) 0.2406(3) -0.0007(6) 0.0553(14) Uani 1 1 d . . .
H1s1 H 0.7311 0.2688 0.0094 0.083 Uiso 1 1 calc R . .
H1s2 H 0.5789 0.2573 0.0615 0.083 Uiso 1 1 calc R . .
H1s3 H 0.6128 0.2441 -0.0938 0.083 Uiso 1 1 calc R . .
C3S C 0.5002(6) 0.1185(3) 0.4747(6) 0.0614(16) Uani 1 1 d . . .
H3s1 H 0.4459 0.1451 0.5385 0.092 Uiso 1 1 calc R . .
H3s2 H 0.5754 0.0953 0.5235 0.092 Uiso 1 1 calc R . .
H3s3 H 0.4419 0.0838 0.4298 0.092 Uiso 1 1 calc R . .
C4S C 0.6040(8) 0.2540(3) 0.4506(7) 0.075(2) Uani 1 1 d . . .
H4s1 H 0.6383 0.2914 0.3935 0.112 Uiso 1 1 calc R . .
H4s2 H 0.6725 0.243 0.521 0.112 Uiso 1 1 calc R . .
H4s3 H 0.519 0.2689 0.4927 0.112 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N2 2.119(4) . ?
Ru1 N8 2.157(4) . ?
Ru1 S2 2.2546(14) . ?
Ru1 S1 2.2833(13) . ?
Ru1 Cl2 2.4004(14) . ?
Ru1 Cl1 2.4130(14) . ?
S1 O1S 1.488(4) . ?
S1 C2S 1.772(5) . ?
S1 C1S 1.776(5) . ?
S2 O2S 1.468(4) . ?
S2 C4S 1.791(6) . ?
S2 C3S 1.804(6) . ?
N2 C3 1.336(6) . ?
N2 N1 1.362(5) . ?
N1 C5 1.381(6) . ?
N1 C7 1.390(6) . ?
N8 C7 1.343(6) . ?
N8 C9 1.356(6) . ?
N6 C7 1.312(6) . ?
N6 C11 1.324(7) . ?
C5 C4 1.370(8) . ?
C4 C3 1.381(8) . ?
C11 C10 1.353(8) . ?
C10 C9 1.368(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
N2 Ru1 N8 76.42(15) . . ?
N2 Ru1 S2 94.48(11) . . ?
N8 Ru1 S2 170.89(10) . . ?
N2 Ru1 S1 173.14(11) . . ?
N8 Ru1 S1 96.91(10) . . ?
S2 Ru1 S1 92.18(5) . . ?
N2 Ru1 Cl2 88.25(11) . . ?
N8 Ru1 Cl2 86.61(11) . . ?
S2 Ru1 Cl2 92.87(5) . . ?
S1 Ru1 Cl2 89.76(5) . . ?
N2 Ru1 Cl1 91.18(11) . . ?
N8 Ru1 Cl1 89.17(11) . . ?
S2 Ru1 Cl1 91.37(5) . . ?
S1 Ru1 Cl1 90.32(5) . . ?
Cl2 Ru1 Cl1 175.75(5) . . ?
O1S S1 C2S 105.6(3) . . ?
O1S S1 C1S 105.6(3) . . ?
C2S S1 C1S 99.9(3) . . ?
O1S S1 Ru1 115.59(16) . . ?
C2S S1 Ru1 115.2(2) . . ?
C1S S1 Ru1 113.29(19) . . ?
O2S S2 C4S 105.7(3) . . ?
O2S S2 C3S 105.5(3) . . ?
C4S S2 C3S 100.4(3) . . ?
O2S S2 Ru1 120.03(19) . . ?
C4S S2 Ru1 111.4(2) . . ?
C3S S2 Ru1 111.8(2) . . ?
C3 N2 N1 104.6(4) . . ?
C3 N2 Ru1 142.1(4) . . ?
N1 N2 Ru1 113.2(3) . . ?
N2 N1 C5 111.8(4) . . ?
N2 N1 C7 119.9(4) . . ?
C5 N1 C7 128.3(5) . . ?
C7 N8 C9 114.1(4) . . ?
C7 N8 Ru1 115.0(3) . . ?
C9 N8 Ru1 130.9(3) . . ?
C7 N6 C11 114.6(5) . . ?
C4 C5 N1 105.2(5) . . ?
C5 C4 C3 106.9(5) . . ?
N2 C3 C4 111.5(5) . . ?
N6 C7 N8 128.8(4) . . ?
N6 C7 N1 115.8(4) . . ?
N8 C7 N1 115.4(4) . . ?
N6 C11 C10 123.2(5) . . ?
C11 C10 C9 118.2(5) . . ?
N8 C9 C10 121.1(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Ru1 S1 O1S 16.1(10) . . . . ?
N8 Ru1 S1 O1S 2.6(2) . . . . ?
S2 Ru1 S1 O1S -178.0(2) . . . . ?
Cl2 Ru1 S1 O1S 89.2(2) . . . . ?
Cl1 Ru1 S1 O1S -86.6(2) . . . . ?
N2 Ru1 S1 C2S 139.8(10) . . . . ?
N8 Ru1 S1 C2S 126.3(3) . . . . ?
S2 Ru1 S1 C2S -54.3(2) . . . . ?
Cl2 Ru1 S1 C2S -147.1(2) . . . . ?
Cl1 Ru1 S1 C2S 37.1(2) . . . . ?
N2 Ru1 S1 C1S -106.0(10) . . . . ?
N8 Ru1 S1 C1S -119.4(2) . . . . ?
S2 Ru1 S1 C1S 60.0(2) . . . . ?
Cl2 Ru1 S1 C1S -32.9(2) . . . . ?
Cl1 Ru1 S1 C1S 151.4(2) . . . . ?
N2 Ru1 S2 O2S -176.5(3) . . . . ?
N8 Ru1 S2 O2S -178.5(7) . . . . ?
S1 Ru1 S2 O2S 5.1(3) . . . . ?
Cl2 Ru1 S2 O2S 95.0(3) . . . . ?
Cl1 Ru1 S2 O2S -85.2(3) . . . . ?
N2 Ru1 S2 C4S 59.2(3) . . . . ?
N8 Ru1 S2 C4S 57.2(8) . . . . ?
S1 Ru1 S2 C4S -119.1(3) . . . . ?
Cl2 Ru1 S2 C4S -29.2(3) . . . . ?
Cl1 Ru1 S2 C4S 150.5(3) . . . . ?
N2 Ru1 S2 C3S -52.2(3) . . . . ?
N8 Ru1 S2 C3S -54.2(8) . . . . ?
S1 Ru1 S2 C3S 129.4(2) . . . . ?
Cl2 Ru1 S2 C3S -140.7(2) . . . . ?
Cl1 Ru1 S2 C3S 39.1(2) . . . . ?
N8 Ru1 N2 C3 177.0(6) . . . . ?
S2 Ru1 N2 C3 -2.7(6) . . . . ?
S1 Ru1 N2 C3 163.3(7) . . . . ?
Cl2 Ru1 N2 C3 90.1(6) . . . . ?
Cl1 Ru1 N2 C3 -94.1(6) . . . . ?
N8 Ru1 N2 N1 1.6(3) . . . . ?
S2 Ru1 N2 N1 -178.1(3) . . . . ?
S1 Ru1 N2 N1 -12.1(12) . . . . ?
Cl2 Ru1 N2 N1 -85.3(3) . . . . ?
Cl1 Ru1 N2 N1 90.4(3) . . . . ?
C3 N2 N1 C5 0.6(6) . . . . ?
Ru1 N2 N1 C5 177.7(3) . . . . ?
C3 N2 N1 C7 -177.7(4) . . . . ?
Ru1 N2 N1 C7 -0.6(5) . . . . ?
N2 Ru1 N8 C7 -2.5(3) . . . . ?
S2 Ru1 N8 C7 -0.4(10) . . . . ?
S1 Ru1 N8 C7 175.9(3) . . . . ?
Cl2 Ru1 N8 C7 86.5(3) . . . . ?
Cl1 Ru1 N8 C7 -93.9(3) . . . . ?
N2 Ru1 N8 C9 -179.7(5) . . . . ?
S2 Ru1 N8 C9 -177.7(5) . . . . ?
S1 Ru1 N8 C9 -1.4(4) . . . . ?
Cl2 Ru1 N8 C9 -90.7(4) . . . . ?
Cl1 Ru1 N8 C9 88.8(4) . . . . ?
N2 N1 C5 C4 -0.3(6) . . . . ?
C7 N1 C5 C4 177.8(5) . . . . ?
N1 C5 C4 C3 -0.1(6) . . . . ?
N1 N2 C3 C4 -0.7(6) . . . . ?
Ru1 N2 C3 C4 -176.3(4) . . . . ?
C5 C4 C3 N2 0.5(7) . . . . ?
C11 N6 C7 N8 1.1(8) . . . . ?
C11 N6 C7 N1 179.6(5) . . . . ?
C9 N8 C7 N6 -0.8(8) . . . . ?
Ru1 N8 C7 N6 -178.5(4) . . . . ?
C9 N8 C7 N1 -179.3(4) . . . . ?
Ru1 N8 C7 N1 3.0(5) . . . . ?
N2 N1 C7 N6 179.7(4) . . . . ?
C5 N1 C7 N6 1.7(8) . . . . ?
N2 N1 C7 N8 -1.6(6) . . . . ?
C5 N1 C7 N8 -179.6(5) . . . . ?
C7 N6 C11 C10 -0.6(8) . . . . ?
N6 C11 C10 C9 0.0(9) . . . . ?
C7 N8 C9 C10 0.1(7) . . . . ?
Ru1 N8 C9 C10 177.3(4) . . . . ?
C11 C10 C9 N8 0.3(8) . . . . ?

# END of CIF

_database_code_depnum_ccdc_archive 'CCDC 963272'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_pm179

_audit_creation_date             2012-06-04T15:56:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C11 H18 Cl2 N4 O2 Ru1 S2'
_chemical_formula_sum            'C11 H18 Cl2 N4 O2 Ru S2'
_chemical_formula_weight         474.38
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.9179(8)
_cell_length_b                   12.1128(16)
_cell_length_c                   17.981(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1724.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      14
_cell_measurement_theta_max      17
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.33
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.471
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.5992
_exptl_absorpt_correction_T_max  0.6154

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      -0.094043
_diffrn_orient_matrix_ub_12      -0.027196
_diffrn_orient_matrix_ub_13      -0.032303
_diffrn_orient_matrix_ub_21      0.07982
_diffrn_orient_matrix_ub_22      -0.005611
_diffrn_orient_matrix_ub_23      -0.04294
_diffrn_orient_matrix_ub_31      0.027117
_diffrn_orient_matrix_ub_32      -0.077747
_diffrn_orient_matrix_ub_33      0.014336
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_standards_number         1
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
5 -3 0

_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_number            1761
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_full        24.96
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             1761
_reflns_number_gt                1702
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0263P)²+1.6199P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1761
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0208
_refine_ls_wR_factor_ref         0.0585
_refine_ls_wR_factor_gt          0.0575
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_restrained_S_all      1.193
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.063

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.43925(4) 0.48964(3) 0.134240(19) 0.02639(11) Uani 1 1 d . . .
Cl1 Cl 0.34327(19) 0.64430(11) 0.21268(7) 0.0446(3) Uani 1 1 d . . .
Cl2 Cl 0.65357(18) 0.59924(11) 0.07369(7) 0.0422(3) Uani 1 1 d . . .
S1 S 0.24815(15) 0.52458(10) 0.04455(6) 0.0339(3) Uani 1 1 d . . .
S2 S 0.53821(16) 0.34432(10) 0.06977(6) 0.0311(3) Uani 1 1 d . . .
O1S O 0.1242(5) 0.4364(3) 0.0315(2) 0.0557(11) Uani 1 1 d . . .
O2S O 0.5409(5) 0.3502(3) -0.01250(17) 0.0438(9) Uani 1 1 d . . .
N2 N 0.2815(5) 0.3939(3) 0.1966(2) 0.0327(9) Uani 1 1 d . . .
N1 N 0.3438(6) 0.3658(3) 0.2653(2) 0.0346(9) Uani 1 1 d . . .
N8 N 0.5865(5) 0.4573(3) 0.2305(2) 0.0334(9) Uani 1 1 d . . .
N6 N 0.5454(7) 0.4002(3) 0.3562(2) 0.0449(11) Uani 1 1 d . . .
C5 C 0.2364(7) 0.2966(4) 0.3012(3) 0.0441(13) Uani 1 1 d . . .
H5 H 0.2527 0.2655 0.348 0.053 Uiso 1 1 calc R . .
C4 C 0.1006(7) 0.2815(5) 0.2562(3) 0.0469(14) Uani 1 1 d . . .
H4 H 0.0052 0.2392 0.266 0.056 Uiso 1 1 calc R . .
C3 C 0.1351(7) 0.3433(4) 0.1917(3) 0.0412(12) Uani 1 1 d . . .
H3 H 0.0634 0.3478 0.1509 0.049 Uiso 1 1 calc R . .
C7 C 0.5023(6) 0.4084(4) 0.2859(3) 0.0332(11) Uani 1 1 d . . .
C11 C 0.6953(8) 0.4433(5) 0.3725(3) 0.0525(15) Uani 1 1 d . . .
H11 H 0.7336 0.4392 0.4213 0.063 Uiso 1 1 calc R . .
C10 C 0.7956(7) 0.4933(5) 0.3207(3) 0.0530(15) Uani 1 1 d . . .
H10 H 0.9003 0.5221 0.3337 0.064 Uiso 1 1 calc R . .
C9 C 0.7374(7) 0.4997(5) 0.2489(3) 0.0409(11) Uani 1 1 d . . .
H9 H 0.8032 0.5338 0.2127 0.049 Uiso 1 1 calc R . .
C2S C 0.3347(9) 0.5567(6) -0.0444(3) 0.0626(18) Uani 1 1 d . . .
H2s1 H 0.4021 0.496 -0.0615 0.094 Uiso 1 1 calc R . .
H2s2 H 0.4038 0.6216 -0.0405 0.094 Uiso 1 1 calc R . .
H2s3 H 0.2447 0.57 -0.079 0.094 Uiso 1 1 calc R . .
C1S C 0.1286(9) 0.6456(6) 0.0596(4) 0.072(2) Uani 1 1 d . . .
H1s1 H 0.0532 0.6568 0.0185 0.108 Uiso 1 1 calc R . .
H1s2 H 0.2032 0.7077 0.0639 0.108 Uiso 1 1 calc R . .
H1s3 H 0.0644 0.6379 0.1046 0.108 Uiso 1 1 calc R . .
C3S C 0.4374(8) 0.2179(4) 0.0933(3) 0.0441(12) Uani 1 1 d . . .
H3s1 H 0.3198 0.2221 0.0806 0.066 Uiso 1 1 calc R . .
H3s2 H 0.4488 0.2049 0.1457 0.066 Uiso 1 1 calc R . .
H3s3 H 0.4891 0.1585 0.0663 0.066 Uiso 1 1 calc R . .
C4S C 0.7477(6) 0.3120(5) 0.0976(3) 0.0463(13) Uani 1 1 d . . .
H4s1 H 0.785 0.2469 0.0719 0.069 Uiso 1 1 calc R . .
H4s2 H 0.7502 0.299 0.1502 0.069 Uiso 1 1 calc R . .
H4s3 H 0.821 0.3726 0.0856 0.069 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N2 2.039(4) . ?
Ru1 N8 2.123(4) . ?
Ru1 S2 2.2486(12) . ?
Ru1 S1 2.2515(12) . ?
Ru1 Cl2 2.4140(13) . ?
Ru1 Cl1 2.4650(13) . ?
S1 O1S 1.470(4) . ?
S1 C1S 1.765(6) . ?
S1 C2S 1.783(6) . ?
S2 O2S 1.481(3) . ?
S2 C4S 1.776(5) . ?
S2 C3S 1.777(5) . ?
N2 C3 1.314(7) . ?
N2 N1 1.373(5) . ?
N1 C5 1.357(7) . ?
N1 C7 1.407(7) . ?
N8 C7 1.337(6) . ?
N8 C9 1.343(6) . ?
N6 C7 1.312(6) . ?
N6 C11 1.329(8) . ?
C5 C4 1.358(8) . ?
C4 C3 1.408(7) . ?
C11 C10 1.365(9) . ?
C10 C9 1.372(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
N2 Ru1 N8 77.49(16) . . ?
N2 Ru1 S2 92.96(12) . . ?
N8 Ru1 S2 94.84(11) . . ?
N2 Ru1 S1 95.10(12) . . ?
N8 Ru1 S1 170.95(11) . . ?
S2 Ru1 S1 90.69(5) . . ?
N2 Ru1 Cl2 172.25(12) . . ?
N8 Ru1 Cl2 94.77(11) . . ?
S2 Ru1 Cl2 87.31(5) . . ?
S1 Ru1 Cl2 92.64(5) . . ?
N2 Ru1 Cl1 85.92(12) . . ?
N8 Ru1 Cl1 80.98(11) . . ?
S2 Ru1 Cl1 175.81(5) . . ?
S1 Ru1 Cl1 93.42(5) . . ?
Cl2 Ru1 Cl1 93.26(5) . . ?
O1S S1 C1S 105.6(3) . . ?
O1S S1 C2S 105.8(3) . . ?
C1S S1 C2S 99.3(3) . . ?
O1S S1 Ru1 115.23(17) . . ?
C1S S1 Ru1 114.0(2) . . ?
C2S S1 Ru1 115.2(2) . . ?
O2S S2 C4S 106.1(3) . . ?
O2S S2 C3S 106.6(2) . . ?
C4S S2 C3S 99.4(3) . . ?
O2S S2 Ru1 118.83(16) . . ?
C4S S2 Ru1 110.7(2) . . ?
C3S S2 Ru1 113.27(18) . . ?
C3 N2 N1 105.1(4) . . ?
C3 N2 Ru1 140.2(4) . . ?
N1 N2 Ru1 114.6(3) . . ?
C5 N1 N2 110.9(4) . . ?
C5 N1 C7 131.3(4) . . ?
N2 N1 C7 117.8(4) . . ?
C7 N8 C9 115.4(4) . . ?
C7 N8 Ru1 114.6(3) . . ?
C9 N8 Ru1 128.3(4) . . ?
C7 N6 C11 114.5(5) . . ?
N1 C5 C4 107.2(5) . . ?
C5 C4 C3 105.4(5) . . ?
N2 C3 C4 111.4(5) . . ?
N6 C7 N8 128.4(5) . . ?
N6 C7 N1 117.3(5) . . ?
N8 C7 N1 114.2(4) . . ?
N6 C11 C10 122.8(5) . . ?
C11 C10 C9 118.2(5) . . ?
N8 C9 C10 120.6(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Ru1 S1 O1S -31.0(2) . . . . ?
N8 Ru1 S1 O1S -65.7(7) . . . . ?
S2 Ru1 S1 O1S 62.1(2) . . . . ?
Cl2 Ru1 S1 O1S 149.4(2) . . . . ?
Cl1 Ru1 S1 O1S -117.2(2) . . . . ?
N2 Ru1 S1 C1S 91.5(3) . . . . ?
N8 Ru1 S1 C1S 56.8(8) . . . . ?
S2 Ru1 S1 C1S -175.5(3) . . . . ?
Cl2 Ru1 S1 C1S -88.2(3) . . . . ?
Cl1 Ru1 S1 C1S 5.3(3) . . . . ?
N2 Ru1 S1 C2S -154.6(3) . . . . ?
N8 Ru1 S1 C2S 170.7(7) . . . . ?
S2 Ru1 S1 C2S -61.6(3) . . . . ?
Cl2 Ru1 S1 C2S 25.7(3) . . . . ?
Cl1 Ru1 S1 C2S 119.2(3) . . . . ?
N2 Ru1 S2 O2S 129.8(2) . . . . ?
N8 Ru1 S2 O2S -152.5(2) . . . . ?
S1 Ru1 S2 O2S 34.7(2) . . . . ?
Cl2 Ru1 S2 O2S -57.9(2) . . . . ?
Cl1 Ru1 S2 O2S -155.8(7) . . . . ?
N2 Ru1 S2 C4S -107.0(2) . . . . ?
N8 Ru1 S2 C4S -29.4(2) . . . . ?
S1 Ru1 S2 C4S 157.8(2) . . . . ?
Cl2 Ru1 S2 C4S 65.2(2) . . . . ?
Cl1 Ru1 S2 C4S -32.6(7) . . . . ?
N2 Ru1 S2 C3S 3.5(2) . . . . ?
N8 Ru1 S2 C3S 81.2(2) . . . . ?
S1 Ru1 S2 C3S -91.6(2) . . . . ?
Cl2 Ru1 S2 C3S 175.8(2) . . . . ?
Cl1 Ru1 S2 C3S 77.9(7) . . . . ?
N8 Ru1 N2 C3 -172.4(6) . . . . ?
S2 Ru1 N2 C3 -78.1(5) . . . . ?
S1 Ru1 N2 C3 12.8(5) . . . . ?
Cl2 Ru1 N2 C3 -169.9(6) . . . . ?
Cl1 Ru1 N2 C3 105.9(5) . . . . ?
N8 Ru1 N2 N1 3.5(3) . . . . ?
S2 Ru1 N2 N1 97.8(3) . . . . ?
S1 Ru1 N2 N1 -171.3(3) . . . . ?
Cl2 Ru1 N2 N1 6.0(11) . . . . ?
Cl1 Ru1 N2 N1 -78.2(3) . . . . ?
C3 N2 N1 C5 1.1(5) . . . . ?
Ru1 N2 N1 C5 -176.2(3) . . . . ?
C3 N2 N1 C7 179.7(4) . . . . ?
Ru1 N2 N1 C7 2.4(5) . . . . ?
N2 Ru1 N8 C7 -9.2(3) . . . . ?
S2 Ru1 N8 C7 -101.2(3) . . . . ?
S1 Ru1 N8 C7 26.3(9) . . . . ?
Cl2 Ru1 N8 C7 171.1(3) . . . . ?
Cl1 Ru1 N8 C7 78.6(3) . . . . ?
N2 Ru1 N8 C9 -173.3(4) . . . . ?
S2 Ru1 N8 C9 94.7(4) . . . . ?
S1 Ru1 N8 C9 -137.8(6) . . . . ?
Cl2 Ru1 N8 C9 7.0(4) . . . . ?
Cl1 Ru1 N8 C9 -85.5(4) . . . . ?
N2 N1 C5 C4 -1.4(6) . . . . ?
C7 N1 C5 C4 -179.7(5) . . . . ?
N1 C5 C4 C3 1.0(6) . . . . ?
N1 N2 C3 C4 -0.4(6) . . . . ?
Ru1 N2 C3 C4 175.7(4) . . . . ?
C5 C4 C3 N2 -0.4(6) . . . . ?
C11 N6 C7 N8 -2.6(7) . . . . ?
C11 N6 C7 N1 -179.1(4) . . . . ?
C9 N8 C7 N6 2.7(7) . . . . ?
Ru1 N8 C7 N6 -163.5(4) . . . . ?
C9 N8 C7 N1 179.3(4) . . . . ?
Ru1 N8 C7 N1 13.1(5) . . . . ?
C5 N1 C7 N6 -15.3(7) . . . . ?
N2 N1 C7 N6 166.5(4) . . . . ?
C5 N1 C7 N8 167.7(5) . . . . ?
N2 N1 C7 N8 -10.5(6) . . . . ?
C7 N6 C11 C10 0.8(8) . . . . ?
N6 C11 C10 C9 0.6(9) . . . . ?
C7 N8 C9 C10 -1.0(7) . . . . ?
Ru1 N8 C9 C10 162.9(4) . . . . ?
C11 C10 C9 N8 -0.4(8) . . . . ?

# END of CIF

_database_code_depnum_ccdc_archive 'CCDC 963273'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_mcj05

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H12 Cl3 N4 O Rh S'
_chemical_formula_weight         433.55

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'
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'
Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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'

_cell_length_a                   17.8313(16)
_cell_length_b                   7.6272(7)
_cell_length_c                   10.6810(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1452.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7703
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      33.16

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    1.866
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9291
_exptl_absorpt_correction_T_max  0.9816
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            9994
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         33.17
_reflns_number_total             4919
_reflns_number_gt                4792
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0321P)²+0.2797P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_number_reflns         4919
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0584
_refine_ls_wR_factor_gt          0.0578
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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


C3 C 0.84819(11) 0.5242(3) -0.2150(2) 0.0163(4) Uani 1 1 d . . .
H3 H 0.8078 0.4474 -0.2338 0.020 Uiso 1 1 calc R . .
C4 C 0.89419(12) 0.6058(3) -0.30503(18) 0.0189(4) Uani 1 1 d . . .
H4 H 0.8907 0.5955 -0.3935 0.023 Uiso 1 1 calc R . .
C5 C 0.94509(12) 0.7035(3) -0.23811(19) 0.0184(4) Uani 1 1 d . . .
H5 H 0.9841 0.7744 -0.2716 0.022 Uiso 1 1 calc R . .
C7 C 0.96600(11) 0.7317(2) -0.00537(19) 0.0152(3) Uani 1 1 d . . .
C11 C 1.05647(12) 0.8944(2) 0.0849(2) 0.0219(4) Uani 1 1 d . . .
H11 H 1.0973 0.9741 0.0797 0.026 Uiso 1 1 calc R . .
C10 C 1.03504(12) 0.8311(2) 0.2009(2) 0.0194(4) Uani 1 1 d . . .
H10 H 1.0601 0.8681 0.2748 0.023 Uiso 1 1 calc R . .
C9 C 0.97614(11) 0.7121(2) 0.20696(19) 0.0168(3) Uani 1 1 d . . .
H9 H 0.9604 0.6680 0.2859 0.020 Uiso 1 1 calc R . .
C1S C 0.82902(12) 0.1778(2) 0.2915(2) 0.0181(3) Uani 1 1 d . . .
H1SA H 0.8072 0.1422 0.3718 0.027 Uiso 1 1 calc R . .
H1SB H 0.8805 0.1335 0.2855 0.027 Uiso 1 1 calc R . .
H1SC H 0.7990 0.1295 0.2228 0.027 Uiso 1 1 calc R . .
C2S C 0.73656(13) 0.4625(3) 0.3290(2) 0.0190(4) Uani 1 1 d . . .
H2SA H 0.7314 0.5897 0.3384 0.028 Uiso 1 1 calc R . .
H2SB H 0.7259 0.4053 0.4093 0.028 Uiso 1 1 calc R . .
H2SC H 0.7010 0.4206 0.2657 0.028 Uiso 1 1 calc R . .
Cl1 Cl 0.77713(3) 0.74868(5) 0.11697(4) 0.01783(9) Uani 1 1 d . . .
Cl2 Cl 0.74214(3) 0.34016(6) 0.02291(4) 0.01606(8) Uani 1 1 d . . .
Cl3 Cl 0.92486(3) 0.25345(5) 0.03557(5) 0.01768(8) Uani 1 1 d . . .
N2 N 0.86912(10) 0.56930(19) -0.10082(15) 0.0134(3) Uani 1 1 d . . .
N1 N 0.92884(9) 0.6791(2) -0.11385(14) 0.0147(3) Uani 1 1 d . . .
N6 N 1.02118(10) 0.8464(2) -0.01998(17) 0.0191(3) Uani 1 1 d . . .
N8 N 0.94130(9) 0.65877(18) 0.10200(15) 0.0140(3) Uani 1 1 d . . .
O1S O 0.88304(11) 0.48052(18) 0.37499(17) 0.0203(3) Uani 1 1 d . . .
RH1 Rh 0.848676(7) 0.496608(14) 0.08013(3) 0.01079(4) Uani 1 1 d . . .
S1 S 0.82978(3) 0.41125(5) 0.28119(4) 0.01371(8) 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
C3 N2 1.321(3) . ?
C3 C4 1.409(3) . ?
C4 C5 1.375(3) . ?
C5 N1 1.371(2) . ?
C7 N6 1.326(2) . ?
C7 N8 1.348(2) . ?
C7 N1 1.394(3) . ?
C11 N6 1.336(3) . ?
C11 C10 1.383(3) . ?
C10 C9 1.390(3) . ?
C9 N8 1.345(2) . ?
C1S S1 1.7839(17) . ?
C2S S1 1.782(2) . ?
Cl1 RH1 2.3406(5) . ?
Cl2 RH1 2.3251(5) . ?
Cl3 RH1 2.3476(5) . ?
N2 N1 1.362(2) . ?
N2 RH1 2.0435(16) . ?
N8 RH1 2.0766(15) . ?
O1S S1 1.4781(17) . ?
RH1 S1 2.2691(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
N2 C3 C4 110.50(18) . . ?
C5 C4 C3 105.63(18) . . ?
N1 C5 C4 106.87(17) . . ?
N6 C7 N8 127.92(19) . . ?
N6 C7 N1 116.41(18) . . ?
N8 C7 N1 115.67(16) . . ?
N6 C11 C10 121.66(18) . . ?
C11 C10 C9 118.60(19) . . ?
N8 C9 C10 120.51(19) . . ?
C3 N2 N1 106.66(15) . . ?
C3 N2 RH1 138.78(14) . . ?
N1 N2 RH1 113.76(11) . . ?
N2 N1 C5 110.34(16) . . ?
N2 N1 C7 117.63(15) . . ?
C5 N1 C7 131.70(17) . . ?
C7 N6 C11 115.57(18) . . ?
C9 N8 C7 115.69(16) . . ?
C9 N8 RH1 129.89(13) . . ?
C7 N8 RH1 114.19(12) . . ?
N2 RH1 N8 78.64(6) . . ?
N2 RH1 S1 178.07(5) . . ?
N8 RH1 S1 100.52(5) . . ?
N2 RH1 Cl2 92.08(5) . . ?
N8 RH1 Cl2 170.09(5) . . ?
S1 RH1 Cl2 88.866(18) . . ?
N2 RH1 Cl1 91.91(5) . . ?
N8 RH1 Cl1 85.72(4) . . ?
S1 RH1 Cl1 89.751(19) . . ?
Cl2 RH1 Cl1 91.171(18) . . ?
N2 RH1 Cl3 85.37(5) . . ?
N8 RH1 Cl3 91.90(4) . . ?
S1 RH1 Cl3 92.932(19) . . ?
Cl2 RH1 Cl3 90.804(18) . . ?
Cl1 RH1 Cl3 176.70(2) . . ?
O1S S1 C2S 109.05(11) . . ?
O1S S1 C1S 108.65(9) . . ?
C2S S1 C1S 101.19(10) . . ?
O1S S1 RH1 116.33(7) . . ?
C2S S1 RH1 110.30(7) . . ?
C1S S1 RH1 110.24(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 N1 -0.1(2) . . . . ?
N6 C11 C10 C9 1.2(3) . . . . ?
C11 C10 C9 N8 0.6(3) . . . . ?
C4 C3 N2 N1 -0.4(2) . . . . ?
C4 C3 N2 RH1 -168.89(15) . . . . ?
C3 N2 N1 C5 0.3(2) . . . . ?
RH1 N2 N1 C5 172.07(12) . . . . ?
C3 N2 N1 C7 -173.80(16) . . . . ?
RH1 N2 N1 C7 -2.1(2) . . . . ?
C4 C5 N1 N2 -0.1(2) . . . . ?
C4 C5 N1 C7 172.90(18) . . . . ?
N6 C7 N1 N2 -176.26(16) . . . . ?
N8 C7 N1 N2 3.9(2) . . . . ?
N6 C7 N1 C5 11.1(3) . . . . ?
N8 C7 N1 C5 -168.75(19) . . . . ?
N8 C7 N6 C11 0.2(3) . . . . ?
N1 C7 N6 C11 -179.59(17) . . . . ?
C10 C11 N6 C7 -1.6(3) . . . . ?
C10 C9 N8 C7 -1.8(3) . . . . ?
C10 C9 N8 RH1 -175.84(14) . . . . ?
N6 C7 N8 C9 1.4(3) . . . . ?
N1 C7 N8 C9 -178.73(16) . . . . ?
N6 C7 N8 RH1 176.46(16) . . . . ?
N1 C7 N8 RH1 -3.7(2) . . . . ?
C3 N2 RH1 N8 168.0(2) . . . . ?
N1 N2 RH1 N8 0.03(12) . . . . ?
C3 N2 RH1 S1 103.8(14) . . . . ?
N1 N2 RH1 S1 -64.1(14) . . . . ?
C3 N2 RH1 Cl2 -15.5(2) . . . . ?
N1 N2 RH1 Cl2 176.52(12) . . . . ?
C3 N2 RH1 Cl1 -106.8(2) . . . . ?
N1 N2 RH1 Cl1 85.28(12) . . . . ?
C3 N2 RH1 Cl3 75.1(2) . . . . ?
N1 N2 RH1 Cl3 -92.84(12) . . . . ?
C9 N8 RH1 N2 176.15(17) . . . . ?
C7 N8 RH1 N2 2.01(12) . . . . ?
C9 N8 RH1 S1 -5.61(17) . . . . ?
C7 N8 RH1 S1 -179.76(11) . . . . ?
C9 N8 RH1 Cl2 155.3(2) . . . . ?
C7 N8 RH1 Cl2 -18.8(3) . . . . ?
C9 N8 RH1 Cl1 83.33(16) . . . . ?
C7 N8 RH1 Cl1 -90.81(12) . . . . ?
C9 N8 RH1 Cl3 -98.95(16) . . . . ?
C7 N8 RH1 Cl3 86.91(12) . . . . ?
N2 RH1 S1 O1S 62.9(14) . . . . ?
N8 RH1 S1 O1S -0.85(9) . . . . ?
Cl2 RH1 S1 O1S -177.63(8) . . . . ?
Cl1 RH1 S1 O1S -86.45(8) . . . . ?
Cl3 RH1 S1 O1S 91.62(8) . . . . ?
N2 RH1 S1 C2S -172.2(13) . . . . ?
N8 RH1 S1 C2S 123.99(9) . . . . ?
Cl2 RH1 S1 C2S -52.78(8) . . . . ?
Cl1 RH1 S1 C2S 38.39(8) . . . . ?
Cl3 RH1 S1 C2S -143.53(8) . . . . ?
N2 RH1 S1 C1S -61.3(14) . . . . ?
N8 RH1 S1 C1S -125.10(9) . . . . ?
Cl2 RH1 S1 C1S 58.13(8) . . . . ?
Cl1 RH1 S1 C1S 149.30(8) . . . . ?
Cl3 RH1 S1 C1S -32.62(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         1.112
_refine_diff_density_min         -1.285
_refine_diff_density_rms         0.103
_database_code_depnum_ccdc_archive 'CCDC 973048'
