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

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

data_C16H18N4O2Scompound12a
_database_code_depnum_ccdc_archive 'CCDC 1018428'
_audit_update_record             
;
2014-08-07 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        12a
_chemical_name_common            'Rhodium complex'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N4 O2 S'
_chemical_formula_sum            'C16 H18 N4 O2 S'
_chemical_formula_weight         330.40

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.2251(1)
_cell_length_b                   10.3695(1)
_cell_length_c                   9.9358(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.2510(7)
_cell_angle_gamma                90.00
_cell_volume                     845.095(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6624
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      28.42

_exptl_crystal_description       cubic
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9323
_exptl_absorpt_correction_T_max  0.9682
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'BRUKER SMART APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6855
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2791
_reflns_number_gt                2739
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL PyMOL and PLATON'
_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)+(0.0511P)²+0.1012P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_number_reflns         2791
_refine_ls_number_parameters     210
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
S1 S 1.06349(4) 0.25293(4) 0.01311(4) 0.04412(13) Uani 1 1 d . . .
O1 O 1.01938(18) 0.37474(14) -0.04499(14) 0.0578(4) Uani 1 1 d . . .
O2 O 1.19737(17) 0.18322(18) -0.03400(16) 0.0669(4) Uani 1 1 d . . .
N1 N 0.90673(18) 0.15876(14) -0.00912(14) 0.0425(3) Uani 1 1 d . . .
H1N H 0.9149 0.0855 -0.0487 0.051 Uiso 1 1 calc R . .
N2 N 0.5966(3) 0.02622(19) -0.06892(19) 0.0688(5) Uani 1 1 d . . .
N3 N 0.4845(3) -0.0098(2) -0.14708(18) 0.0782(7) Uani 1 1 d . . .
N4 N 0.3858(4) -0.0547(4) -0.2171(3) 0.1211(12) Uani 1 1 d . . .
C1 C 0.6935(3) 0.1634(3) -0.3031(2) 0.0655(6) Uani 1 1 d . . .
H1 H 0.7397 0.0825 -0.2864 0.079 Uiso 1 1 calc R . .
C2 C 0.6967(3) 0.2174(3) -0.4287(3) 0.0832(8) Uani 1 1 d . . .
H2 H 0.7454 0.1737 -0.4969 0.100 Uiso 1 1 calc R . .
C3 C 0.6273(4) 0.3373(4) -0.4537(3) 0.0923(10) Uani 1 1 d . . .
H3 H 0.6265 0.3733 -0.5395 0.111 Uiso 1 1 calc R . .
C4 C 0.5599(4) 0.4028(3) -0.3527(3) 0.0845(8) Uani 1 1 d . . .
H4 H 0.5156 0.4843 -0.3691 0.101 Uiso 1 1 calc R . .
C5 C 0.5573(3) 0.3486(2) -0.2269(2) 0.0655(6) Uani 1 1 d . . .
H5 H 0.5113 0.3938 -0.1583 0.079 Uiso 1 1 calc R . .
C6 C 0.62238(19) 0.22782(18) -0.20113(17) 0.0450(4) Uani 1 1 d . . .
C7 C 0.6092(2) 0.16938(18) -0.06412(19) 0.0469(4) Uani 1 1 d . . .
H7 H 0.5093 0.2026 -0.0286 0.056 Uiso 1 1 calc R . .
C8 C 0.7506(2) 0.19979(18) 0.03904(17) 0.0430(4) Uani 1 1 d . . .
H8 H 0.7548 0.2936 0.0507 0.052 Uiso 1 1 calc R . .
C9 C 0.7214(3) 0.1401(2) 0.17621(19) 0.0605(5) Uani 1 1 d . . .
H9A H 0.7281 0.0478 0.1702 0.091 Uiso 1 1 calc R . .
H9B H 0.6151 0.1641 0.2015 0.091 Uiso 1 1 calc R . .
H9C H 0.8026 0.1708 0.2430 0.091 Uiso 1 1 calc R . .
C10 C 1.0963(2) 0.27603(19) 0.18896(18) 0.0484(4) Uani 1 1 d . . .
C11 C 1.0278(3) 0.3802(2) 0.2494(2) 0.0580(5) Uani 1 1 d . . .
H11 H 0.9742 0.4440 0.1974 0.070 Uiso 1 1 calc R . .
C12 C 1.0400(3) 0.3884(3) 0.3896(2) 0.0731(7) Uani 1 1 d . . .
H12 H 0.9940 0.4587 0.4307 0.088 Uiso 1 1 calc R . .
C13 C 1.1181(3) 0.2958(3) 0.4690(2) 0.0748(8) Uani 1 1 d . . .
C14 C 1.1882(4) 0.1949(4) 0.4055(3) 0.0896(9) Uani 1 1 d . . .
H14 H 1.2447 0.1326 0.4575 0.108 Uiso 1 1 calc R . .
C15 C 1.1775(3) 0.1827(3) 0.2659(2) 0.0715(6) Uani 1 1 d . . .
H15 H 1.2245 0.1126 0.2251 0.086 Uiso 1 1 calc R . .
C16 C 1.1252(4) 0.3038(5) 0.6212(3) 0.1165(14) Uani 1 1 d . . .
H16A H 1.1253 0.3927 0.6484 0.175 Uiso 1 1 calc R . .
H16B H 1.2229 0.2628 0.6588 0.175 Uiso 1 1 calc R . .
H16C H 1.0319 0.2612 0.6532 0.175 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4245(15) . ?
S1 O2 1.4250(15) . ?
S1 N1 1.6195(15) . ?
S1 C10 1.7644(18) . ?
N1 C8 1.466(2) . ?
N1 H1N 0.8600 . ?
N2 N3 1.219(3) . ?
N2 C7 1.489(3) . ?
N3 N4 1.129(3) . ?
C1 C2 1.370(3) . ?
C1 C6 1.380(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.501(3) . ?
C7 C8 1.525(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.532(3) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.375(3) . ?
C10 C11 1.377(3) . ?
C11 C12 1.392(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(4) . ?
C13 C16 1.512(3) . ?
C14 C15 1.389(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O1 S1 O2 119.77(10) . . ?
O1 S1 N1 107.64(8) . . ?
O2 S1 N1 106.03(9) . . ?
O1 S1 C10 107.26(9) . . ?
O2 S1 C10 109.20(9) . . ?
N1 S1 C10 106.19(8) . . ?
C8 N1 S1 119.22(12) . . ?
C8 N1 H1N 120.4 . . ?
S1 N1 H1N 120.4 . . ?
N3 N2 C7 112.0(2) . . ?
N4 N3 N2 173.5(3) . . ?
C2 C1 C6 120.6(2) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 118.80(17) . . ?
C1 C6 C7 122.24(19) . . ?
N2 C7 C6 112.52(16) . . ?
N2 C7 C8 106.00(16) . . ?
C6 C7 C8 115.04(14) . . ?
N2 C7 H7 107.7 . . ?
C6 C7 H7 107.7 . . ?
C8 C7 H7 107.7 . . ?
N1 C8 C7 111.30(14) . . ?
N1 C8 C9 111.83(16) . . ?
C7 C8 C9 110.62(15) . . ?
N1 C8 H8 107.6 . . ?
C7 C8 H8 107.6 . . ?
C9 C8 H8 107.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 120.51(19) . . ?
C15 C10 S1 119.15(17) . . ?
C11 C10 S1 120.05(16) . . ?
C10 C11 C12 118.9(2) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 121.9(2) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C14 C13 C12 117.7(2) . . ?
C14 C13 C16 121.1(3) . . ?
C12 C13 C16 121.2(3) . . ?
C13 C14 C15 122.1(3) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C10 C15 C14 118.9(3) . . ?
C10 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
O1 S1 N1 C8 -55.10(15) . . . . ?
O2 S1 N1 C8 175.60(13) . . . . ?
C10 S1 N1 C8 59.52(15) . . . . ?
C7 N2 N3 N4 174(2) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C1 C2 C3 C4 1.8(4) . . . . ?
C2 C3 C4 C5 -1.6(5) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 1.5(3) . . . . ?
C4 C5 C6 C7 -176.9(2) . . . . ?
C2 C1 C6 C5 -1.3(3) . . . . ?
C2 C1 C6 C7 177.0(2) . . . . ?
N3 N2 C7 C6 -54.7(2) . . . . ?
N3 N2 C7 C8 178.74(18) . . . . ?
C5 C6 C7 N2 148.54(19) . . . . ?
C1 C6 C7 N2 -29.7(3) . . . . ?
C5 C6 C7 C8 -89.9(2) . . . . ?
C1 C6 C7 C8 91.8(2) . . . . ?
S1 N1 C8 C7 137.43(13) . . . . ?
S1 N1 C8 C9 -98.28(17) . . . . ?
N2 C7 C8 N1 67.74(18) . . . . ?
C6 C7 C8 N1 -57.3(2) . . . . ?
N2 C7 C8 C9 -57.2(2) . . . . ?
C6 C7 C8 C9 177.75(17) . . . . ?
O1 S1 C10 C15 -164.41(17) . . . . ?
O2 S1 C10 C15 -33.2(2) . . . . ?
N1 S1 C10 C15 80.72(18) . . . . ?
O1 S1 C10 C11 21.75(17) . . . . ?
O2 S1 C10 C11 152.95(16) . . . . ?
N1 S1 C10 C11 -93.13(16) . . . . ?
C15 C10 C11 C12 -0.9(3) . . . . ?
S1 C10 C11 C12 172.82(16) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 1.6(4) . . . . ?
C11 C12 C13 C16 -177.8(2) . . . . ?
C12 C13 C14 C15 -2.1(4) . . . . ?
C16 C13 C14 C15 177.3(3) . . . . ?
C11 C10 C15 C14 0.5(3) . . . . ?
S1 C10 C15 C14 -173.4(2) . . . . ?
C13 C14 C15 C10 1.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.031
