# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2016

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

data_46
_database_code_depnum_ccdc_archive 'CCDC 1498776'
_audit_update_record             
;
2016-08-11 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;
_audit_creation_date             2015-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C14 H20 Cl2 N O3 Rh S2'
_chemical_formula_sum            'C14 H20 Cl2 N O3 Rh S2'
_chemical_formula_weight         488.26
_chemical_oxdiff_formula         'C1 H1 O1 N1 Br1 Ni1'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Rh -1.11611 0.93962 19.29570 14.35010 4.73425 1.28918 0.75154 8.21758 25.87490
98.60620 5.32800006866
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.9953(9)
_cell_length_b                   15.618(2)
_cell_length_c                   13.4715(15)
_cell_angle_alpha                90
_cell_angle_beta                 103.827(12)
_cell_angle_gamma                90
_cell_volume                     1837.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2375
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4950
_cell_measurement_theta_min      3.3600
_exptl_absorpt_coefficient_mu    1.459
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.7646
_exptl_crystal_colour            'red brown crystals'
_exptl_crystal_F_000             982.0121
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_av_unetI/netI     0.1174
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7465
_diffrn_reflns_theta_full        26.3723
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.11
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0233
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.9973
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -94.00  -64.00   1.0000   23.6400
omega____ theta____ kappa____ phi______ frames
    -      -18.7829 -178.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00   37.00   1.0000   23.6400
omega____ theta____ kappa____ phi______ frames
    -      -18.7829   57.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega  -86.00   42.00   1.0000   23.6400
omega____ theta____ kappa____ phi______ frames
    -      -18.7829    0.0000 -180.0000 128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0576380000
_diffrn_orient_matrix_UB_12      -0.0300321000
_diffrn_orient_matrix_UB_13      -0.0036239000
_diffrn_orient_matrix_UB_21      0.0231121000
_diffrn_orient_matrix_UB_22      0.0265542000
_diffrn_orient_matrix_UB_23      -0.0363435000
_diffrn_orient_matrix_UB_31      0.0522714000
_diffrn_orient_matrix_UB_32      0.0212999000
_diffrn_orient_matrix_UB_33      0.0401249000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -11
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              -7
_reflns_number_gt                2596
_reflns_number_total             3753
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         3.8380
_refine_diff_density_min         -2.1634
_refine_diff_density_rms         0.3635
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             6.5405
_refine_ls_goodness_of_fit_ref   1.0663
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.0956
_refine_ls_restrained_S_all      1.0663
_refine_ls_shift/su_max          0.1771
_refine_ls_shift/su_mean         0.0509
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1339P)²+15.5071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2539
_refine_ls_wR_factor_ref         0.2872
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3aa(H3aa), C1(H1), C0aa(H0aa), C2aa(H2aa), C2(H2)
2.b Idealised Me refined as rotating group:
 C4aa(H4aa,H4ab,H4ac), C6(H6a,H6b,H6c), C7(H7a,H7b,H7c), C11(H11a,H11b,H11c),
 C13(H13a,H13b,H13c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Rh1 Rh 0.19433(9) 0.37969(6) 0.25443(7) 0.0361(3) Uani 1.000000 .
S0aa S 0.0070(3) 0.31811(18) 0.1288(2) 0.0396(7) Uani 1.000000 .
Cl Cl 0.3753(3) 0.4422(2) 0.3900(2) 0.0506(8) Uani 1.000000 .
S1 S 0.3640(3) 0.4048(2) 0.1560(2) 0.0467(8) Uani 1.000000 .
O1aa O 0.1024(8) 0.4947(5) 0.2095(6) 0.0409(18) Uani 1.000000 .
O3 O 0.3149(11) 0.3810(7) 0.0474(7) 0.066(3) Uani 1.000000 .
N N 0.0350(10) 0.3842(6) 0.3475(6) 0.0334(19) Uani 1.000000 .
C3aa C -0.1950(14) 0.6148(8) 0.2862(12) 0.055(3) Uani 1.000000 .
H3aa H -0.2472(14) 0.6663(8) 0.2704(12) 0.066(4) Uiso 1.000000 R
C C -0.0045(12) 0.5175(7) 0.2573(9) 0.041(3) Uani 1.000000 .
C1 C -0.2300(13) 0.5636(8) 0.3601(11) 0.054(3) Uani 1.000000 .
H1 H -0.3041(13) 0.5803(8) 0.3939(11) 0.065(4) Uiso 1.000000 R
C3 C -0.0441(11) 0.4618(7) 0.3291(8) 0.034(2) Uani 1.000000 .
C0aa C -0.0844(14) 0.5929(8) 0.2339(10) 0.049(3) Uani 1.000000 .
H0aa H -0.0648(14) 0.6289(8) 0.1835(10) 0.059(3) Uiso 1.000000 R
C4 C -0.1526(11) 0.4860(8) 0.3838(9) 0.041(3) Uani 1.000000 .
C4aa C 0.0677(18) 0.2325(10) 0.0649(13) 0.072(5) Uani 1.000000 .
H4aa H 0.155(8) 0.250(2) 0.040(8) 0.109(7) Uiso 1.000000 GR
H4ab H 0.095(12) 0.185(3) 0.111(3) 0.109(7) Uiso 1.000000 GR
H4ac H -0.014(5) 0.215(5) 0.008(5) 0.109(7) Uiso 1.000000 GR
C1aa C -0.0015(13) 0.3308(8) 0.4133(10) 0.049(3) Uani 1.000000 .
C2aa C -0.1059(14) 0.3521(10) 0.4710(10) 0.056(3) Uani 1.000000 .
H2aa H -0.1231(14) 0.3138(10) 0.5200(10) 0.067(4) Uiso 1.000000 R
C6 C 0.5483(14) 0.3618(11) 0.2046(13) 0.072(5) Uani 1.000000 .
H6a H 0.547(3) 0.3015(17) 0.191(8) 0.108(7) Uiso 1.000000 GR
H6b H 0.620(3) 0.389(5) 0.172(7) 0.108(7) Uiso 1.000000 GR
H6c H 0.579(6) 0.371(7) 0.2770(19) 0.108(7) Uiso 1.000000 GR
C7 C 0.0737(17) 0.2430(11) 0.4308(13) 0.081(5) Uani 1.000000 .
H7a H 0.065(13) 0.215(3) 0.3662(15) 0.122(8) Uiso 1.000000 GR
H7b H 0.180(4) 0.2495(12) 0.465(9) 0.122(8) Uiso 1.000000 GR
H7c H 0.023(10) 0.209(3) 0.472(8) 0.122(8) Uiso 1.000000 GR
C2 C -0.1813(14) 0.4261(9) 0.4572(10) 0.054(3) Uani 1.000000 .
H2 H -0.2523(14) 0.4388(9) 0.4952(10) 0.065(4) Uiso 1.000000 R
C11 C 0.4034(15) 0.5149(10) 0.1610(11) 0.062(4) Uani 1.000000 .
H11a H 0.313(4) 0.5461(10) 0.165(8) 0.094(6) Uiso 1.000000 GR
H11b H 0.484(8) 0.5272(14) 0.220(4) 0.094(6) Uiso 1.000000 GR
H11c H 0.434(11) 0.5317(16) 0.100(4) 0.094(6) Uiso 1.000000 GR
C13 C -0.0555(17) 0.3916(9) 0.0270(12) 0.064(4) Uani 1.000000 .
H13a H -0.099(11) 0.441(3) 0.052(2) 0.095(6) Uiso 1.000000 GR
H13b H 0.030(3) 0.409(5) 0.000(5) 0.095(6) Uiso 1.000000 GR
H13c H -0.132(9) 0.365(2) -0.026(4) 0.095(6) Uiso 1.000000 GR
O4aa O -0.1261(9) 0.2912(6) 0.1644(8) 0.062(3) Uani 1.000000 .
Cl8 Cl 0.3108(4) 0.2442(2) 0.2905(3) 0.0594(9) Uani 1.000000 .


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 S0aa 2.295(3) . ?
Rh1 Cl 2.349(3) . ?
Rh1 S1 2.282(3) . ?
Rh1 O1aa 2.010(7) . ?
Rh1 N 2.119(8) . ?
Rh1 Cl8 2.359(3) . ?
S0aa C4aa 1.748(14) . ?
S0aa C13 1.773(14) . ?
S0aa O4aa 1.454(8) . ?
S1 O3 1.472(10) . ?
S1 C6 1.763(13) . ?
S1 C11 1.754(15) . ?
O1aa C 1.327(13) . ?
N C3 1.396(13) . ?
N C1aa 1.314(15) . ?
C3aa H3aa 0.9300 . ?
C3aa C1 1.37(2) . ?
C3aa C0aa 1.392(18) . ?
C C3 1.409(16) . ?
C C0aa 1.377(16) . ?
C1 H1 0.9300 . ?
C1 C4 1.397(17) . ?
C3 C4 1.408(14) . ?
C0aa H0aa 0.9300 . ?
C4 C2 1.428(18) . ?
C4aa H4aa 0.9600 . ?
C4aa H4ab 0.9600 . ?
C4aa H4ac 0.9600 . ?
C1aa C2aa 1.395(17) . ?
C1aa C7 1.522(19) . ?
C2aa H2aa 0.9300 . ?
C2aa C2 1.33(2) . ?
C6 H6a 0.9600 . ?
C6 H6b 0.9600 . ?
C6 H6c 0.9600 . ?
C7 H7a 0.9600 . ?
C7 H7b 0.9600 . ?
C7 H7c 0.9600 . ?
C2 H2 0.9300 . ?
C11 H11a 0.9600 . ?
C11 H11b 0.9600 . ?
C11 H11c 0.9600 . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?

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
Cl Rh1 S0aa 176.33(10) . . ?
S1 Rh1 S0aa 96.83(10) . . ?
S1 Rh1 Cl 86.83(11) . . ?
O1aa Rh1 S0aa 88.6(2) . . ?
O1aa Rh1 Cl 91.3(2) . . ?
O1aa Rh1 S1 87.5(2) . . ?
N Rh1 S0aa 88.2(2) . . ?
N Rh1 Cl 88.1(2) . . ?
N Rh1 S1 168.2(3) . . ?
N Rh1 O1aa 82.0(3) . . ?
Cl8 Rh1 S0aa 89.30(12) . . ?
Cl8 Rh1 Cl 91.21(13) . . ?
Cl8 Rh1 S1 87.00(12) . . ?
Cl8 Rh1 O1aa 173.8(2) . . ?
Cl8 Rh1 N 103.8(3) . . ?
C4aa S0aa Rh1 115.0(5) . . ?
C13 S0aa Rh1 109.9(4) . . ?
C13 S0aa C4aa 101.1(8) . . ?
O4aa S0aa Rh1 113.3(4) . . ?
O4aa S0aa C4aa 108.7(7) . . ?
O4aa S0aa C13 108.0(7) . . ?
O3 S1 Rh1 116.8(4) . . ?
C6 S1 Rh1 114.8(6) . . ?
C6 S1 O3 107.7(7) . . ?
C11 S1 Rh1 107.7(5) . . ?
C11 S1 O3 107.2(7) . . ?
C11 S1 C6 101.3(7) . . ?
C O1aa Rh1 112.8(7) . . ?
C3 N Rh1 108.2(6) . . ?
C1aa N Rh1 133.7(8) . . ?
C1aa N C3 118.1(9) . . ?
C1 C3aa H3aa 118.7(7) . . ?
C0aa C3aa H3aa 118.7(8) . . ?
C0aa C3aa C1 122.7(12) . . ?
C3 C O1aa 119.9(10) . . ?
C0aa C O1aa 121.2(11) . . ?
C0aa C C3 118.8(10) . . ?
H1 C1 C3aa 120.5(7) . . ?
C4 C1 C3aa 119.0(11) . . ?
C4 C1 H1 120.5(7) . . ?
C C3 N 117.1(9) . . ?
C4 C3 N 121.9(10) . . ?
C4 C3 C 121.0(10) . . ?
C C0aa C3aa 119.5(13) . . ?
H0aa C0aa C3aa 120.3(8) . . ?
H0aa C0aa C 120.3(8) . . ?
C3 C4 C1 118.9(11) . . ?
C2 C4 C1 124.4(11) . . ?
C2 C4 C3 116.7(11) . . ?
H4aa C4aa S0aa 109.5 . . ?
H4ab C4aa S0aa 109.5 . . ?
H4ab C4aa H4aa 109.5 . . ?
H4ac C4aa S0aa 109.5 . . ?
H4ac C4aa H4aa 109.5 . . ?
H4ac C4aa H4ab 109.5 . . ?
C2aa C1aa N 122.3(12) . . ?
C7 C1aa N 120.2(11) . . ?
C7 C1aa C2aa 117.5(12) . . ?
H2aa C2aa C1aa 119.4(8) . . ?
C2 C2aa C1aa 121.1(12) . . ?
C2 C2aa H2aa 119.4(7) . . ?
H6a C6 S1 109.5 . . ?
H6b C6 S1 109.5 . . ?
H6b C6 H6a 109.5 . . ?
H6c C6 S1 109.5 . . ?
H6c C6 H6a 109.5 . . ?
H6c C6 H6b 109.5 . . ?
H7a C7 C1aa 109.5 . . ?
H7b C7 C1aa 109.5 . . ?
H7b C7 H7a 109.5 . . ?
H7c C7 C1aa 109.5 . . ?
H7c C7 H7a 109.5 . . ?
H7c C7 H7b 109.5 . . ?
C2aa C2 C4 119.7(11) . . ?
H2 C2 C4 120.2(7) . . ?
H2 C2 C2aa 120.2(7) . . ?
H11a C11 S1 109.5 . . ?
H11b C11 S1 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 S1 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
H13a C13 S0aa 109.5 . . ?
H13b C13 S0aa 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 S0aa 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        'rhodium(III) complex'
_chemical_name_common            '[Rh(MQ)(DMSO)2Cl2]'
