# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1443845'
_audit_update_record             
;
2015-12-22 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N2 S2'
_chemical_formula_weight         288.42

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.674(4)
_cell_length_b                   12.171(5)
_cell_length_c                   13.450(5)
_cell_angle_alpha                98.037(6)
_cell_angle_beta                 91.768(6)
_cell_angle_gamma                101.969(4)
_cell_volume                     1531.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1710
_cell_measurement_theta_min      2.459
_cell_measurement_theta_max      21.977

_exptl_crystal_description       blocky
_exptl_crystal_colour            colorles
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.336
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruke Smart Aepex CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10245
_diffrn_reflns_av_unetI/netI     0.0876
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.532
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             6918
_reflns_number_gt                3512
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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     
'w=1/[σ²(Fo²)+(0.0732P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6918
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1378
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1802
_refine_ls_wR_factor_gt          0.1522
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.09397(13) 0.34101(10) 0.97518(7) 0.0613(3) Uani 1 1 d . . . . .
S2 S 0.71480(13) 0.35596(10) 1.02953(8) 0.0681(4) Uani 1 1 d . . . . .
S3 S 0.43812(12) 0.64178(9) 0.51633(8) 0.0611(3) Uani 1 1 d . . . . .
S4 S 1.04658(12) 0.66296(9) 0.49582(8) 0.0604(3) Uani 1 1 d . . . . .
N1 N 0.2438(3) 0.0511(2) 0.7370(2) 0.0433(7) Uani 1 1 d . . . . .
N2 N 0.4622(3) 0.0345(2) 0.7767(2) 0.0466(8) Uani 1 1 d . . . . .
H2A H 0.5379 0.0079 0.7760 0.056 Uiso 1 1 calc R U . . .
N3 N 0.7180(3) 0.9576(2) 0.7649(2) 0.0433(7) Uani 1 1 d . . . . .
N4 N 0.9439(3) 0.9796(2) 0.7325(2) 0.0461(7) Uani 1 1 d . . . . .
H4A H 1.0332 1.0083 0.7354 0.055 Uiso 1 1 calc R U . . .
C1 C 0.3437(4) -0.0077(3) 0.7175(3) 0.0486(9) Uani 1 1 d . . . . .
H1B H 0.3328 -0.0711 0.6682 0.058 Uiso 1 1 calc R U . . .
C2 C 0.3040(4) 0.1368(3) 0.8143(2) 0.0383(8) Uani 1 1 d . . . . .
C3 C 0.4403(4) 0.1286(3) 0.8392(3) 0.0427(9) Uani 1 1 d . . . . .
C4 C 0.2619(6) 0.2034(5) 1.0455(3) 0.0850(16) Uani 1 1 d . . . . .
H4B H 0.2313 0.2395 1.1065 0.127 Uiso 1 1 calc R U . . .
H4C H 0.2289 0.1226 1.0398 0.127 Uiso 1 1 calc R U . . .
H4D H 0.3635 0.2212 1.0469 0.127 Uiso 1 1 calc R U . . .
C5 C 0.2026(4) 0.2453(3) 0.9568(3) 0.0503(10) Uani 1 1 d . . . . .
C6 C 0.2189(4) 0.2169(3) 0.8570(2) 0.0397(8) Uani 1 1 d . . . . .
C7 C 0.1390(4) 0.2723(3) 0.7964(3) 0.0437(9) Uani 1 1 d . . . . .
H7A H 0.1373 0.2612 0.7265 0.052 Uiso 1 1 calc R U . . .
C8 C 0.0662(4) 0.3421(3) 0.8490(3) 0.0443(9) Uani 1 1 d . . . . .
C9 C -0.0250(5) 0.4145(4) 0.8111(3) 0.0654(12) Uani 1 1 d . . . . .
H9A H -0.0624 0.4546 0.8670 0.098 Uiso 1 1 calc R U . . .
H9B H 0.0305 0.4681 0.7742 0.098 Uiso 1 1 calc R U . . .
H9C H -0.1016 0.3673 0.7678 0.098 Uiso 1 1 calc R U . . .
C10 C 0.5378(5) 0.3952(3) 0.8747(3) 0.0742(13) Uani 1 1 d . . . . .
H10A H 0.5839 0.4707 0.9048 0.111 Uiso 1 1 calc R U . . .
H10B H 0.5609 0.3827 0.8057 0.111 Uiso 1 1 calc R U . . .
H10C H 0.4372 0.3864 0.8779 0.111 Uiso 1 1 calc R U . . .
C11 C 0.5872(4) 0.3104(3) 0.9306(3) 0.0508(10) Uani 1 1 d . . . . .
C12 C 0.5498(4) 0.1944(3) 0.9139(3) 0.0447(9) Uani 1 1 d . . . . .
C13 C 0.6280(4) 0.1438(3) 0.9802(3) 0.0544(10) Uani 1 1 d . . . . .
H13A H 0.6165 0.0656 0.9776 0.065 Uiso 1 1 calc R U . . .
C14 C 0.7198(4) 0.2194(4) 1.0467(3) 0.0608(11) Uani 1 1 d . . . . .
C15 C 0.8151(5) 0.1969(5) 1.1278(4) 0.0972(18) Uani 1 1 d . . . . .
H15A H 0.8684 0.2677 1.1632 0.146 Uiso 1 1 calc R U . . .
H15B H 0.7591 0.1559 1.1739 0.146 Uiso 1 1 calc R U . . .
H15C H 0.8788 0.1526 1.0983 0.146 Uiso 1 1 calc R U . . .
C16 C 0.8483(4) 1.0203(3) 0.7880(3) 0.0468(9) Uani 1 1 d . . . . .
H16A H 0.8701 1.0844 0.8369 0.056 Uiso 1 1 calc R U . . .
C17 C 0.7339(4) 0.8719(3) 0.6885(3) 0.0399(8) Uani 1 1 d . . . . .
C18 C 0.8742(4) 0.8839(3) 0.6701(3) 0.0399(8) Uani 1 1 d . . . . .
C19 C 0.6552(5) 0.8037(4) 0.4560(3) 0.0747(14) Uani 1 1 d . . . . .
H19A H 0.6087 0.7635 0.3934 0.112 Uiso 1 1 calc R U . . .
H19B H 0.6516 0.8825 0.4609 0.112 Uiso 1 1 calc R U . . .
H19C H 0.7522 0.7966 0.4589 0.112 Uiso 1 1 calc R U . . .
C20 C 0.5822(4) 0.7549(3) 0.5414(3) 0.0466(9) Uani 1 1 d . . . . .
C21 C 0.6107(4) 0.7845(3) 0.6422(3) 0.0396(8) Uani 1 1 d . . . . .
C22 C 0.5118(4) 0.7176(3) 0.6981(3) 0.0500(10) Uani 1 1 d . . . . .
H22A H 0.5154 0.7289 0.7680 0.060 Uiso 1 1 calc R U . . .
C23 C 0.4127(4) 0.6368(3) 0.6415(3) 0.0567(10) Uani 1 1 d . . . . .
C24 C 0.2977(5) 0.5479(4) 0.6735(4) 0.0993(19) Uani 1 1 d . . . . .
H24A H 0.2443 0.5029 0.6150 0.149 Uiso 1 1 calc R U . . .
H24B H 0.3391 0.4999 0.7108 0.149 Uiso 1 1 calc R U . . .
H24C H 0.2360 0.5841 0.7150 0.149 Uiso 1 1 calc R U . . .
C25 C 0.8429(5) 0.6175(3) 0.6359(3) 0.0657(12) Uani 1 1 d . . . . .
H25A H 0.8554 0.5431 0.6090 0.099 Uiso 1 1 calc R U . . .
H25B H 0.8680 0.6322 0.7068 0.099 Uiso 1 1 calc R U . . .
H25C H 0.7458 0.6215 0.6245 0.099 Uiso 1 1 calc R U . . .
C26 C 0.9352(4) 0.7037(3) 0.5852(3) 0.0456(9) Uani 1 1 d . . . . .
C27 C 0.9521(4) 0.8191(3) 0.5991(3) 0.0415(8) Uani 1 1 d . . . . .
C28 C 1.0573(4) 0.8729(3) 0.5392(3) 0.0491(9) Uani 1 1 d . . . . .
H28A H 1.0827 0.9513 0.5421 0.059 Uiso 1 1 calc R U . . .
C29 C 1.1172(4) 0.8006(3) 0.4780(3) 0.0508(10) Uani 1 1 d . . . . .
C30 C 1.2292(5) 0.8273(4) 0.4056(3) 0.0761(14) Uani 1 1 d . . . . .
H30A H 1.2501 0.7580 0.3727 0.114 Uiso 1 1 calc R U . . .
H30B H 1.1961 0.8674 0.3563 0.114 Uiso 1 1 calc R U . . .
H30C H 1.3132 0.8738 0.4414 0.114 Uiso 1 1 calc R U . . .


_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 C8 1.712(4) . ?
S1 C5 1.722(4) . ?
S2 C14 1.719(4) . ?
S2 C11 1.735(4) . ?
S3 C23 1.717(4) . ?
S3 C20 1.731(4) . ?
S4 C26 1.729(4) . ?
S4 C29 1.726(4) . ?
N1 C1 1.329(4) . ?
N1 C2 1.384(4) . ?
N2 C1 1.340(5) . ?
N2 C3 1.380(4) . ?
N2 H2A 0.8600 . ?
N3 C16 1.334(4) . ?
N3 C17 1.395(4) . ?
N4 C16 1.337(4) . ?
N4 C18 1.371(4) . ?
N4 H4A 0.8600 . ?
C1 H1B 0.9300 . ?
C2 C3 1.378(5) . ?
C2 C6 1.471(4) . ?
C3 C12 1.460(5) . ?
C4 C5 1.505(5) . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C4 H4D 0.9600 . ?
C5 C6 1.360(5) . ?
C6 C7 1.432(5) . ?
C7 C8 1.353(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.495(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.503(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.366(5) . ?
C12 C13 1.433(5) . ?
C13 C14 1.348(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.498(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9300 . ?
C17 C18 1.368(5) . ?
C17 C21 1.478(5) . ?
C18 C27 1.477(5) . ?
C19 C20 1.497(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.357(5) . ?
C21 C22 1.427(5) . ?
C22 C23 1.349(5) . ?
C22 H22A 0.9300 . ?
C23 C24 1.501(6) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.488(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.365(5) . ?
C27 C28 1.427(5) . ?
C28 C29 1.351(5) . ?
C28 H28A 0.9300 . ?
C29 C30 1.495(5) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
C8 S1 C5 93.26(17) . . ?
C14 S2 C11 92.77(19) . . ?
C23 S3 C20 93.13(18) . . ?
C26 S4 C29 93.60(17) . . ?
C1 N1 C2 104.6(3) . . ?
C1 N2 C3 107.4(3) . . ?
C1 N2 H2A 126.3 . . ?
C3 N2 H2A 126.3 . . ?
C16 N3 C17 104.9(3) . . ?
C16 N4 C18 107.9(3) . . ?
C16 N4 H4A 126.1 . . ?
C18 N4 H4A 126.1 . . ?
N1 C1 N2 112.5(3) . . ?
N1 C1 H1B 123.7 . . ?
N2 C1 H1B 123.7 . . ?
C3 C2 N1 110.2(3) . . ?
C3 C2 C6 130.8(3) . . ?
N1 C2 C6 119.0(3) . . ?
N2 C3 C2 105.3(3) . . ?
N2 C3 C12 121.2(3) . . ?
C2 C3 C12 133.4(3) . . ?
C5 C4 H4B 109.5 . . ?
C5 C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 C4 H4D 109.5 . . ?
H4B C4 H4D 109.5 . . ?
H4C C4 H4D 109.5 . . ?
C6 C5 C4 129.3(3) . . ?
C6 C5 S1 110.8(3) . . ?
C4 C5 S1 120.0(3) . . ?
C5 C6 C7 111.7(3) . . ?
C5 C6 C2 125.3(3) . . ?
C7 C6 C2 123.0(3) . . ?
C8 C7 C6 114.5(3) . . ?
C8 C7 H7A 122.7 . . ?
C6 C7 H7A 122.7 . . ?
C7 C8 C9 129.1(3) . . ?
C7 C8 S1 109.8(3) . . ?
C9 C8 S1 121.2(3) . . ?
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 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C10 129.5(4) . . ?
C12 C11 S2 110.3(3) . . ?
C10 C11 S2 120.2(3) . . ?
C11 C12 C13 112.3(3) . . ?
C11 C12 C3 124.4(3) . . ?
C13 C12 C3 123.3(3) . . ?
C14 C13 C12 114.1(4) . . ?
C14 C13 H13A 123.0 . . ?
C12 C13 H13A 123.0 . . ?
C13 C14 C15 128.4(4) . . ?
C13 C14 S2 110.6(3) . . ?
C15 C14 S2 121.0(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 N4 111.7(3) . . ?
N3 C16 H16A 124.1 . . ?
N4 C16 H16A 124.1 . . ?
C18 C17 N3 109.2(3) . . ?
C18 C17 C21 129.7(3) . . ?
N3 C17 C21 121.1(3) . . ?
C17 C18 N4 106.2(3) . . ?
C17 C18 C27 133.1(3) . . ?
N4 C18 C27 120.7(3) . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C19 130.1(3) . . ?
C21 C20 S3 110.3(3) . . ?
C19 C20 S3 119.6(3) . . ?
C20 C21 C22 112.1(3) . . ?
C20 C21 C17 123.9(3) . . ?
C22 C21 C17 123.9(3) . . ?
C23 C22 C21 114.8(3) . . ?
C23 C22 H22A 122.6 . . ?
C21 C22 H22A 122.6 . . ?
C22 C23 C24 129.7(4) . . ?
C22 C23 S3 109.6(3) . . ?
C24 C23 S3 120.6(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C25 129.9(3) . . ?
C27 C26 S4 109.7(3) . . ?
C25 C26 S4 120.4(3) . . ?
C26 C27 C28 112.8(3) . . ?
C26 C27 C18 124.7(3) . . ?
C28 C27 C18 122.5(3) . . ?
C29 C28 C27 114.6(3) . . ?
C29 C28 H28A 122.7 . . ?
C27 C28 H28A 122.7 . . ?
C28 C29 C30 128.8(4) . . ?
C28 C29 S4 109.3(3) . . ?
C30 C29 S4 121.9(3) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.061

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1443846'
_audit_update_record             
;
2015-12-22 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C15 H17 N2 S2), Cl6 Re'
_chemical_formula_sum            'C30 H34 Cl6 N4 Re S4'
_chemical_formula_weight         977.75

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'
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'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.888(3)
_cell_length_b                   10.355(3)
_cell_length_c                   10.532(4)
_cell_angle_alpha                101.349(4)
_cell_angle_beta                 106.929(4)
_cell_angle_gamma                93.294(4)
_cell_volume                     902.3(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7254
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.68

_exptl_crystal_description       blocky
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_F_000             483
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    4.072
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.391
_exptl_absorpt_correction_T_max  0.480
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Smart Aepex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6409
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.074
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             3132
_reflns_number_gt                3116
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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.
In the final Fourier difference map,the deepest hole and the highest peak 
were -2.208 and 1.635, respectively, which are in the vicinity of the Re atoms. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3132
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0831
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.05221(12) 0.82023(10) -0.08616(10) 0.0185(2) Uani 1 1 d . . . . .
S2 S 0.81929(12) 1.07259(10) 0.33509(11) 0.0176(2) Uani 1 1 d . . . . .
N1 N 1.0009(4) 0.5155(4) 0.2173(4) 0.0191(7) Uani 1 1 d . . . . .
H1A H 1.0510 0.4612 0.1776 0.023 Uiso 1 1 d R U . . .
N2 N 0.8699(4) 0.5976(3) 0.3478(3) 0.0162(7) Uani 1 1 d . . . . .
H2A H 0.8191 0.6046 0.4058 0.019 Uiso 1 1 d R U . . .
C1 C 0.9357(5) 0.4912(4) 0.3091(4) 0.0203(9) Uani 1 1 d . . . . .
H1B H 0.9359 0.4135 0.3410 0.024 Uiso 1 1 calc R U . . .
C2 C 0.9770(5) 0.6410(4) 0.1944(4) 0.0155(8) Uani 1 1 d . . . . .
C3 C 0.8947(5) 0.6948(4) 0.2794(4) 0.0155(8) Uani 1 1 d . . . . .
C4 C 0.7701(5) 0.7823(5) -0.0239(4) 0.0214(9) Uani 1 1 d . . . . .
H4B H 0.7142 0.7150 0.0020 0.032 Uiso 1 1 calc R U . . .
H4C H 0.7234 0.7786 -0.1192 0.032 Uiso 1 1 calc R U . . .
H4D H 0.7637 0.8680 0.0278 0.032 Uiso 1 1 calc R U . . .
C5 C 0.9405(5) 0.7591(4) 0.0035(4) 0.0154(8) Uani 1 1 d . . . . .
C6 C 1.0320(5) 0.6948(4) 0.0946(4) 0.0161(8) Uani 1 1 d . . . . .
C7 C 1.1919(5) 0.6954(4) 0.0903(4) 0.0209(9) Uani 1 1 d . . . . .
H7A H 1.2683 0.6558 0.1457 0.025 Uiso 1 1 calc R U . . .
C8 C 1.2207(5) 0.7590(5) -0.0016(4) 0.0202(9) Uani 1 1 d . . . . .
C9 C 1.3720(5) 0.7769(6) -0.0372(5) 0.0341(12) Uani 1 1 d . . . . .
H9A H 1.4534 0.7389 0.0208 0.051 Uiso 1 1 calc R U . . .
H9B H 1.4043 0.8698 -0.0245 0.051 Uiso 1 1 calc R U . . .
H9C H 1.3545 0.7334 -0.1305 0.051 Uiso 1 1 calc R U . . .
C10 C 1.1003(5) 0.9668(4) 0.3273(4) 0.0191(8) Uani 1 1 d . . . . .
H10A H 1.1550 0.8954 0.3567 0.029 Uiso 1 1 calc R U . . .
H10B H 1.1482 1.0489 0.3910 0.029 Uiso 1 1 calc R U . . .
H10C H 1.1069 0.9717 0.2390 0.029 Uiso 1 1 calc R U . . .
C11 C 0.9301(5) 0.9424(4) 0.3200(4) 0.0151(8) Uani 1 1 d . . . . .
C12 C 0.8389(5) 0.8242(4) 0.3020(4) 0.0146(8) Uani 1 1 d . . . . .
C13 C 0.6801(5) 0.8418(4) 0.3036(4) 0.0160(8) Uani 1 1 d . . . . .
H13A H 0.6050 0.7719 0.2956 0.019 Uiso 1 1 calc R U . . .
C14 C 0.6506(5) 0.9691(4) 0.3179(4) 0.0193(9) Uani 1 1 d . . . . .
C15 C 0.4981(5) 1.0231(5) 0.3203(5) 0.0267(10) Uani 1 1 d . . . . .
H15A H 0.4172 0.9511 0.3047 0.040 Uiso 1 1 calc R U . . .
H15B H 0.4668 1.0720 0.2502 0.040 Uiso 1 1 calc R U . . .
H15C H 0.5127 1.0808 0.4074 0.040 Uiso 1 1 calc R U . . .
Re1 Re 0.5000 0.5000 0.5000 0.01233(11) Uani 1 2 d S . P . .
Cl1 Cl 0.69203(12) 0.35270(10) 0.49772(11) 0.0242(2) Uani 1 1 d . . . . .
Cl2 Cl 0.47898(12) 0.50521(10) 0.27301(10) 0.0220(2) Uani 1 1 d . . . . .
Cl3 Cl 0.70784(11) 0.67919(9) 0.58319(10) 0.0181(2) 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
S1 C8 1.730(4) . ?
S1 C5 1.729(4) . ?
S2 C14 1.735(4) . ?
S2 C11 1.724(4) . ?
N1 C1 1.319(6) . ?
N1 C2 1.385(5) . ?
N1 H1A 0.8573 . ?
N2 C1 1.326(6) . ?
N2 C3 1.390(5) . ?
N2 H2A 0.8544 . ?
C1 H1B 0.9300 . ?
C2 C3 1.371(6) . ?
C2 C6 1.467(6) . ?
C3 C12 1.455(6) . ?
C4 C5 1.499(5) . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C4 H4D 0.9600 . ?
C5 C6 1.373(6) . ?
C6 C7 1.435(6) . ?
C7 C8 1.346(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.508(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.496(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.377(6) . ?
C12 C13 1.438(6) . ?
C13 C14 1.346(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.501(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
Re1 Cl1 2.3556(11) 2_666 ?
Re1 Cl1 2.3556(11) . ?
Re1 Cl2 2.3547(13) . ?
Re1 Cl2 2.3548(13) 2_666 ?
Re1 Cl3 2.3763(11) . ?
Re1 Cl3 2.3763(11) 2_666 ?

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
C8 S1 C5 92.9(2) . . ?
C14 S2 C11 93.0(2) . . ?
C1 N1 C2 110.5(4) . . ?
C1 N1 H1A 124.6 . . ?
C2 N1 H1A 124.9 . . ?
C1 N2 C3 110.1(4) . . ?
C1 N2 H2A 124.6 . . ?
C3 N2 H2A 125.3 . . ?
N2 C1 N1 107.5(4) . . ?
N2 C1 H1B 126.2 . . ?
N1 C1 H1B 126.2 . . ?
C3 C2 N1 106.1(4) . . ?
C3 C2 C6 130.8(4) . . ?
N1 C2 C6 123.1(4) . . ?
C2 C3 N2 105.8(4) . . ?
C2 C3 C12 131.1(4) . . ?
N2 C3 C12 123.1(4) . . ?
C5 C4 H4B 109.5 . . ?
C5 C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 C4 H4D 109.5 . . ?
H4B C4 H4D 109.5 . . ?
H4C C4 H4D 109.5 . . ?
C6 C5 C4 130.2(4) . . ?
C6 C5 S1 109.9(3) . . ?
C4 C5 S1 119.8(3) . . ?
C5 C6 C7 113.0(4) . . ?
C5 C6 C2 123.8(4) . . ?
C7 C6 C2 123.1(4) . . ?
C8 C7 C6 113.5(4) . . ?
C8 C7 H7A 123.3 . . ?
C6 C7 H7A 123.3 . . ?
C7 C8 C9 128.6(4) . . ?
C7 C8 S1 110.7(3) . . ?
C9 C8 S1 120.6(3) . . ?
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 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C10 129.2(4) . . ?
C12 C11 S2 110.1(3) . . ?
C10 C11 S2 120.7(3) . . ?
C11 C12 C13 112.7(4) . . ?
C11 C12 C3 124.0(4) . . ?
C13 C12 C3 123.3(4) . . ?
C14 C13 C12 113.6(4) . . ?
C14 C13 H13A 123.2 . . ?
C12 C13 H13A 123.2 . . ?
C13 C14 C15 128.1(4) . . ?
C13 C14 S2 110.5(3) . . ?
C15 C14 S2 121.4(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Cl1 Re1 Cl1 180.0 2_666 . ?
Cl1 Re1 Cl2 91.08(4) 2_666 . ?
Cl1 Re1 Cl2 88.92(4) . . ?
Cl1 Re1 Cl2 88.92(4) 2_666 2_666 ?
Cl1 Re1 Cl2 91.07(4) . 2_666 ?
Cl2 Re1 Cl2 180.0 . 2_666 ?
Cl1 Re1 Cl3 91.34(4) 2_666 . ?
Cl1 Re1 Cl3 88.66(4) . . ?
Cl2 Re1 Cl3 91.31(4) . . ?
Cl2 Re1 Cl3 88.69(4) 2_666 . ?
Cl1 Re1 Cl3 88.66(4) 2_666 2_666 ?
Cl1 Re1 Cl3 91.34(4) . 2_666 ?
Cl2 Re1 Cl3 88.69(4) . 2_666 ?
Cl2 Re1 Cl3 91.31(4) 2_666 2_666 ?
Cl3 Re1 Cl3 180.0 . 2_666 ?

_refine_diff_density_max         1.635
_refine_diff_density_min         -2.208
_refine_diff_density_rms         0.157

_shelxl_version_number           2014/6

