# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_compound3
_database_code_depnum_ccdc_archive 'CCDC 1001632'
_audit_update_record             
;
2014-05-07 deposited with the CCDC.
2015-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H38 N12 S4'
_chemical_formula_sum            'C36 H38 N12 S4'
_chemical_formula_weight         767.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 '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 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.535(2)
_cell_length_b                   19.120(5)
_cell_length_c                   22.172(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3618.2(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12190
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      31.6

_exptl_crystal_description       needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             1608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.242
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_source                   Synchrotron
_diffrn_radiation_monochromator  Synchrotron
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
CrystalLogic Kappa (3 circle)
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            28222
_diffrn_reflns_av_unetI/netI     0.1539
_diffrn_reflns_av_R_equivalents  0.2717
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.065
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             6895
_reflns_number_gt                6358
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.984

_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       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2012 (Sheldrick, 2012)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;

_refine_special_details          
;
 data above 2theta 50 degrees have been truncated due to a weak 
 diffracting crystal. 
 Hetero atom hydrogen atoms have been refined with bond lenghts restraints
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1875P)²+2.2046P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.10(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6895
_refine_ls_number_parameters     498
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0993
_refine_ls_wR_factor_ref         0.2666
_refine_ls_wR_factor_gt          0.2565
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.4472(2) 0.68498(11) 0.32909(8) 0.0291(5) Uani 1 1 d . . . . .
S2 S 0.2355(2) 0.69393(10) 0.48565(8) 0.0237(5) Uani 1 1 d . . . . .
S3 S 0.1923(2) 0.79600(10) 0.50858(8) 0.0232(5) Uani 1 1 d . . . . .
S4 S -0.0466(2) 0.90998(11) 0.38059(8) 0.0282(5) Uani 1 1 d . . . . .
N1 N 0.4957(8) 0.5584(4) 0.2821(3) 0.0275(15) Uani 1 1 d D . . . .
H1 H 0.459(12) 0.516(3) 0.277(5) 0.04(3) Uiso 1 1 d D . . . .
N2 N 0.3441(8) 0.5632(3) 0.3673(3) 0.0256(14) Uani 1 1 d D . . . .
H2 H 0.293(10) 0.585(4) 0.396(3) 0.03(2) Uiso 1 1 d D . . . .
N3 N 0.3174(7) 0.4918(4) 0.3615(3) 0.0249(14) Uani 1 1 d . . . . .
N4 N 0.1694(8) 0.5589(4) 0.4718(3) 0.0243(14) Uani 1 1 d . . . . .
N5 N 0.0861(8) 0.5773(4) 0.5232(3) 0.0259(14) Uani 1 1 d . . . . .
N6 N 0.0366(8) 0.6769(4) 0.5801(3) 0.0249(13) Uani 1 1 d D . . . .
H6A H 0.063(17) 0.720(3) 0.586(7) 0.08(5) Uiso 1 1 d D . . . .
N7 N 0.4079(7) 0.7610(4) 0.5932(3) 0.0229(13) Uani 1 1 d D . . . .
H7A H 0.387(9) 0.721(2) 0.575(3) 0.009(18) Uiso 1 1 d D . . . .
N8 N 0.3331(7) 0.8754(3) 0.5928(3) 0.0234(13) Uani 1 1 d . . . . .
N9 N 0.2376(7) 0.9221(3) 0.5613(3) 0.0216(12) Uani 1 1 d . . . . .
N10 N 0.0458(8) 1.0410(3) 0.5097(3) 0.0248(13) Uani 1 1 d . . . . .
N11 N 0.0415(8) 0.9819(4) 0.4762(3) 0.0243(13) Uani 1 1 d D . . . .
H11A H 0.113(13) 0.949(6) 0.473(7) 0.09(5) Uiso 1 1 d D . . . .
N12 N -0.1220(8) 1.0407(4) 0.4128(3) 0.0265(14) Uani 1 1 d D . . . .
H12A H -0.100(11) 1.079(3) 0.431(4) 0.03(2) Uiso 1 1 d D . . . .
C1 C 0.6491(10) 0.5328(5) 0.1914(3) 0.0326(18) Uani 1 1 d . . . . .
H1A H 0.6935 0.4927 0.2129 0.049 Uiso 1 1 calc R U . . .
H1B H 0.7278 0.5522 0.1639 0.049 Uiso 1 1 calc R U . . .
H1C H 0.5573 0.5177 0.1683 0.049 Uiso 1 1 calc R U . . .
C2 C 0.6010(10) 0.5877(5) 0.2360(3) 0.0312(18) Uani 1 1 d . . . . .
H2A H 0.6954 0.6072 0.2558 0.037 Uiso 1 1 calc R U . . .
H2B H 0.5472 0.6263 0.2146 0.037 Uiso 1 1 calc R U . . .
C3 C 0.4322(8) 0.5974(4) 0.3249(3) 0.0236(15) Uani 1 1 d . . . . .
C4 C 0.2312(9) 0.4635(4) 0.4021(3) 0.0238(15) Uani 1 1 d . . . . .
C5 C 0.1876(9) 0.3887(4) 0.3987(3) 0.0245(16) Uani 1 1 d . . . . .
C6 C 0.2216(9) 0.3359(5) 0.3590(3) 0.0279(17) Uani 1 1 d . . . . .
H6 H 0.2897 0.3435 0.3258 0.034 Uiso 1 1 calc R U . . .
C7 C 0.1514(10) 0.2685(5) 0.3692(4) 0.0301(17) Uani 1 1 d . . . . .
H7 H 0.1750 0.2311 0.3425 0.036 Uiso 1 1 calc R U . . .
C8 C 0.0515(10) 0.2570(4) 0.4165(4) 0.0297(17) Uani 1 1 d . . . . .
H8 H 0.0084 0.2116 0.4220 0.036 Uiso 1 1 calc R U . . .
C9 C 0.0107(9) 0.3110(4) 0.4574(3) 0.0263(16) Uani 1 1 d . . . . .
C10 C -0.0963(9) 0.3082(4) 0.5064(4) 0.0296(17) Uani 1 1 d . . . . .
H10 H -0.1497 0.2658 0.5152 0.036 Uiso 1 1 calc R U . . .
C11 C -0.1228(10) 0.3659(5) 0.5410(3) 0.0300(18) Uani 1 1 d . . . . .
H11 H -0.1937 0.3622 0.5739 0.036 Uiso 1 1 calc R U . . .
C12 C -0.0491(9) 0.4318(5) 0.5302(3) 0.0265(16) Uani 1 1 d . . . . .
H12 H -0.0721 0.4713 0.5546 0.032 Uiso 1 1 calc R U . . .
C13 C 0.0562(9) 0.4363(4) 0.4834(3) 0.0240(15) Uani 1 1 d . . . . .
C14 C 0.0840(9) 0.3757(4) 0.4470(3) 0.0252(16) Uani 1 1 d . . . . .
C15 C 0.1499(9) 0.4933(4) 0.4560(3) 0.0257(16) Uani 1 1 d . . . . .
C16 C 0.1061(9) 0.6450(4) 0.5344(3) 0.0232(15) Uani 1 1 d . . . . .
C17 C -0.0584(10) 0.6413(5) 0.6256(3) 0.0299(17) Uani 1 1 d . . . . .
H17A H -0.0867 0.5941 0.6108 0.036 Uiso 1 1 calc R U . . .
H17B H -0.1566 0.6679 0.6321 0.036 Uiso 1 1 calc R U . . .
C18 C 0.0286(11) 0.6348(5) 0.6847(4) 0.0338(18) Uani 1 1 d . . . . .
H18A H 0.0582 0.6815 0.6991 0.051 Uiso 1 1 calc R U . . .
H18B H 0.1231 0.6066 0.6787 0.051 Uiso 1 1 calc R U . . .
H18C H -0.0391 0.6122 0.7146 0.051 Uiso 1 1 calc R U . . .
C19 C 0.4177(10) 0.7705(5) 0.7048(3) 0.0329(19) Uani 1 1 d . . . . .
H19A H 0.4880 0.7817 0.7383 0.049 Uiso 1 1 calc R U . . .
H19B H 0.3712 0.7242 0.7112 0.049 Uiso 1 1 calc R U . . .
H19C H 0.3343 0.8056 0.7025 0.049 Uiso 1 1 calc R U . . .
C20 C 0.5094(8) 0.7704(4) 0.6464(3) 0.0223(16) Uani 1 1 d . . . . .
H20A H 0.5667 0.8152 0.6426 0.027 Uiso 1 1 calc R U . . .
H20B H 0.5877 0.7322 0.6476 0.027 Uiso 1 1 calc R U . . .
C21 C 0.3243(8) 0.8119(4) 0.5701(3) 0.0221(15) Uani 1 1 d . . . . .
C22 C 0.2344(8) 0.9854(4) 0.5844(3) 0.0221(15) Uani 1 1 d . . . . .
C23 C 0.3132(8) 1.0156(4) 0.6374(3) 0.0220(15) Uani 1 1 d . . . . .
C24 C 0.4231(9) 0.9924(4) 0.6784(3) 0.0252(16) Uani 1 1 d . . . . .
H24 H 0.4655 0.9466 0.6758 0.030 Uiso 1 1 calc R U . . .
C25 C 0.4710(9) 1.0392(5) 0.7246(3) 0.0284(17) Uani 1 1 d . . . . .
H25 H 0.5468 1.0238 0.7530 0.034 Uiso 1 1 calc R U . . .
C26 C 0.4123(10) 1.1057(5) 0.7298(3) 0.0290(17) Uani 1 1 d . . . . .
H26 H 0.4470 1.1348 0.7619 0.035 Uiso 1 1 calc R U . . .
C27 C 0.3007(9) 1.1316(4) 0.6883(3) 0.0252(16) Uani 1 1 d . . . . .
C28 C 0.2294(9) 1.1992(5) 0.6859(3) 0.0299(17) Uani 1 1 d . . . . .
H28 H 0.2526 1.2326 0.7164 0.036 Uiso 1 1 calc R U . . .
C29 C 0.1282(9) 1.2166(5) 0.6404(4) 0.0300(17) Uani 1 1 d . . . . .
H29 H 0.0847 1.2623 0.6396 0.036 Uiso 1 1 calc R U . . .
C30 C 0.0865(9) 1.1687(4) 0.5947(4) 0.0260(16) Uani 1 1 d . . . . .
H30 H 0.0165 1.1820 0.5634 0.031 Uiso 1 1 calc R U . . .
C31 C 0.1494(8) 1.1024(4) 0.5963(3) 0.0232(15) Uani 1 1 d . . . . .
C32 C 0.2541(8) 1.0853(4) 0.6429(3) 0.0234(15) Uani 1 1 d . . . . .
C33 C 0.1345(8) 1.0405(4) 0.5577(3) 0.0227(15) Uani 1 1 d . . . . .
C34 C -0.0452(9) 0.9823(4) 0.4245(3) 0.0236(15) Uani 1 1 d . . . . .
C35 C -0.2184(9) 1.0541(5) 0.3597(3) 0.0300(18) Uani 1 1 d . . . . .
H35A H -0.3216 1.0722 0.3728 0.036 Uiso 1 1 calc R U . . .
H35B H -0.2362 1.0095 0.3380 0.036 Uiso 1 1 calc R U . . .
C36 C -0.1440(11) 1.1063(5) 0.3168(3) 0.0331(18) Uani 1 1 d . . . . .
H36A H -0.1284 1.1510 0.3377 0.050 Uiso 1 1 calc R U . . .
H36B H -0.2129 1.1134 0.2820 0.050 Uiso 1 1 calc R U . . .
H36C H -0.0426 1.0883 0.3030 0.050 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 C3 1.683(8) . ?
S2 C16 1.806(8) . ?
S2 S3 2.050(3) . ?
S3 C21 1.795(7) . ?
S4 C34 1.691(8) . ?
N1 C3 1.322(10) . ?
N1 C2 1.472(10) . ?
N1 H1 0.88(3) . ?
N2 C3 1.370(10) . ?
N2 N3 1.390(9) . ?
N2 H2 0.88(3) . ?
N3 C4 1.282(10) . ?
N4 C15 1.312(11) . ?
N4 N5 1.389(9) . ?
N5 C16 1.328(11) . ?
N6 C16 1.324(10) . ?
N6 C17 1.462(10) . ?
N6 H6A 0.87(3) . ?
N7 C21 1.312(10) . ?
N7 C20 1.475(9) . ?
N7 H7A 0.87(3) . ?
N8 C21 1.316(10) . ?
N8 N9 1.396(9) . ?
N9 C22 1.315(10) . ?
N10 C33 1.305(10) . ?
N10 N11 1.354(9) . ?
N11 C34 1.365(9) . ?
N11 H11A 0.87(3) . ?
N12 C34 1.321(11) . ?
N12 C35 1.460(9) . ?
N12 H12A 0.86(3) . ?
C1 C2 1.499(12) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 C5 1.478(11) . ?
C4 C15 1.497(10) . ?
C5 C6 1.371(12) . ?
C5 C14 1.411(11) . ?
C6 C7 1.438(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.369(12) . ?
C7 H7 0.9500 . ?
C8 C9 1.418(12) . ?
C8 H8 0.9500 . ?
C9 C14 1.407(12) . ?
C9 C10 1.420(12) . ?
C10 C11 1.363(12) . ?
C10 H10 0.9500 . ?
C11 C12 1.428(12) . ?
C11 H11 0.9500 . ?
C12 C13 1.375(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.431(11) . ?
C13 C15 1.482(11) . ?
C17 C18 1.512(11) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.512(10) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C22 C23 1.472(9) . ?
C22 C33 1.478(11) . ?
C23 C24 1.379(10) . ?
C23 C32 1.429(12) . ?
C24 C25 1.420(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.371(13) . ?
C25 H25 0.9500 . ?
C26 C27 1.415(11) . ?
C26 H26 0.9500 . ?
C27 C32 1.399(11) . ?
C27 C28 1.429(12) . ?
C28 C29 1.369(11) . ?
C28 H28 0.9500 . ?
C29 C30 1.412(11) . ?
C29 H29 0.9500 . ?
C30 C31 1.377(11) . ?
C30 H30 0.9500 . ?
C31 C32 1.403(10) . ?
C31 C33 1.467(11) . ?
C35 C36 1.518(12) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?

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
C16 S2 S3 103.5(3) . . ?
C21 S3 S2 103.7(3) . . ?
C3 N1 C2 122.3(7) . . ?
C3 N1 H1 118(7) . . ?
C2 N1 H1 119(7) . . ?
C3 N2 N3 119.7(6) . . ?
C3 N2 H2 123(6) . . ?
N3 N2 H2 117(6) . . ?
C4 N3 N2 116.4(7) . . ?
C15 N4 N5 113.4(6) . . ?
C16 N5 N4 109.6(6) . . ?
C16 N6 C17 124.2(7) . . ?
C16 N6 H6A 116(10) . . ?
C17 N6 H6A 119(10) . . ?
C21 N7 C20 122.7(6) . . ?
C21 N7 H7A 111(5) . . ?
C20 N7 H7A 126(5) . . ?
C21 N8 N9 111.5(6) . . ?
C22 N9 N8 114.0(6) . . ?
C33 N10 N11 117.1(7) . . ?
N10 N11 C34 118.1(7) . . ?
N10 N11 H11A 128(10) . . ?
C34 N11 H11A 109(10) . . ?
C34 N12 C35 125.9(7) . . ?
C34 N12 H12A 121(6) . . ?
C35 N12 H12A 111(6) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 111.0(7) . . ?
N1 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N1 C3 N2 116.6(7) . . ?
N1 C3 S1 124.7(6) . . ?
N2 C3 S1 118.6(6) . . ?
N3 C4 C5 121.2(7) . . ?
N3 C4 C15 131.7(8) . . ?
C5 C4 C15 107.0(7) . . ?
C6 C5 C14 119.3(8) . . ?
C6 C5 C4 133.8(7) . . ?
C14 C5 C4 106.8(7) . . ?
C5 C6 C7 118.1(7) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C8 C7 C6 121.6(8) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 121.7(8) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C14 C9 C8 115.3(7) . . ?
C14 C9 C10 116.4(7) . . ?
C8 C9 C10 128.3(7) . . ?
C11 C10 C9 120.5(8) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 123.2(7) . . ?
C10 C11 H11 118.4 . . ?
C12 C11 H11 118.4 . . ?
C13 C12 C11 118.0(7) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C12 C13 C14 118.9(7) . . ?
C12 C13 C15 135.0(7) . . ?
C14 C13 C15 105.9(6) . . ?
C9 C14 C5 123.9(7) . . ?
C9 C14 C13 123.1(7) . . ?
C5 C14 C13 112.9(7) . . ?
N4 C15 C13 131.5(7) . . ?
N4 C15 C4 121.2(7) . . ?
C13 C15 C4 107.3(7) . . ?
N6 C16 N5 122.2(7) . . ?
N6 C16 S2 119.6(6) . . ?
N5 C16 S2 118.1(6) . . ?
N6 C17 C18 111.3(7) . . ?
N6 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
N6 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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 . . ?
N7 C20 C19 112.4(6) . . ?
N7 C20 H20A 109.1 . . ?
C19 C20 H20A 109.1 . . ?
N7 C20 H20B 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.9 . . ?
N7 C21 N8 120.4(6) . . ?
N7 C21 S3 120.8(6) . . ?
N8 C21 S3 118.8(6) . . ?
N9 C22 C23 131.5(7) . . ?
N9 C22 C33 120.7(6) . . ?
C23 C22 C33 107.7(6) . . ?
C24 C23 C32 119.0(7) . . ?
C24 C23 C22 135.3(8) . . ?
C32 C23 C22 105.7(6) . . ?
C23 C24 C25 117.9(8) . . ?
C23 C24 H24 121.0 . . ?
C25 C24 H24 121.0 . . ?
C26 C25 C24 122.7(7) . . ?
C26 C25 H25 118.7 . . ?
C24 C25 H25 118.7 . . ?
C25 C26 C27 121.1(8) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C32 C27 C26 115.9(8) . . ?
C32 C27 C28 115.2(7) . . ?
C26 C27 C28 128.9(8) . . ?
C29 C28 C27 121.0(8) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C28 C29 C30 122.1(8) . . ?
C28 C29 H29 119.0 . . ?
C30 C29 H29 119.0 . . ?
C31 C30 C29 118.7(7) . . ?
C31 C30 H30 120.7 . . ?
C29 C30 H30 120.7 . . ?
C30 C31 C32 118.9(7) . . ?
C30 C31 C33 133.9(7) . . ?
C32 C31 C33 107.2(7) . . ?
C27 C32 C31 124.2(8) . . ?
C27 C32 C23 123.4(7) . . ?
C31 C32 C23 112.4(7) . . ?
N10 C33 C31 121.3(7) . . ?
N10 C33 C22 131.8(7) . . ?
C31 C33 C22 106.9(6) . . ?
N12 C34 N11 116.0(7) . . ?
N12 C34 S4 125.1(6) . . ?
N11 C34 S4 118.8(6) . . ?
N12 C35 C36 112.6(7) . . ?
N12 C35 H35A 109.1 . . ?
C36 C35 H35A 109.1 . . ?
N12 C35 H35B 109.1 . . ?
C36 C35 H35B 109.1 . . ?
H35A C35 H35B 107.8 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

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
N2 H2 S2 0.88(3) 2.92(5) 3.741(7) 156(8) .
N2 H2 N4 0.88(3) 2.05(6) 2.757(9) 137(8) .
N6 H6A S1 0.87(3) 2.80(12) 3.407(7) 129(12) 3_466
N6 H6A S3 0.87(3) 2.50(12) 3.077(7) 125(12) .
N7 H7A S2 0.87(3) 2.42(6) 3.080(7) 132(6) .
N7 H7A S4 0.87(3) 2.76(6) 3.343(7) 126(6) 3_566
N11 H11A N9 0.87(3) 2.28(14) 2.768(9) 115(12) .

_refine_diff_density_max         1.015
_refine_diff_density_min         -1.728
_refine_diff_density_rms         0.163

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_compound4
_database_code_depnum_ccdc_archive 'CCDC 1001633'
_audit_update_record             
;
2014-05-07 deposited with the CCDC.
2015-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N6 S2'
_chemical_formula_sum            'C20 H20 N6 S2'
_chemical_formula_weight         408.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 '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 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1188 0.1164 '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                   7.859(7)
_cell_length_b                   11.040(9)
_cell_length_c                   12.049(9)
_cell_angle_alpha                90.546(6)
_cell_angle_beta                 95.3880(10)
_cell_angle_gamma                110.304(13)
_cell_volume                     975.1(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2445
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      26.8

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.227
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.68890
_diffrn_source                   Synchrotron
_diffrn_radiation_monochromator  Synchrotron
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
CrystalLogic Kappa (3 circle)
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            6825
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.577
_diffrn_reflns_theta_max         24.354
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measured_fraction_theta_full 0.899
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_Laue_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_point_group_measured_fraction_full 0.899
_reflns_number_total             3176
_reflns_number_gt                2442
_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       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0688P)²+0.9976P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3176
_refine_ls_number_parameters     269
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1510
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.27173(11) 0.64594(9) 0.45023(7) 0.0348(3) Uani 1 1 d . . . . .
H1 H 0.083(5) 0.334(3) 0.343(3) 0.041(11) Uiso 1 1 d D . . . .
S2 S -0.01402(12) 1.04912(9) 0.15880(8) 0.0373(3) Uani 1 1 d . . . . .
H2 H 0.046(6) 0.600(4) 0.262(3) 0.043(12) Uiso 1 1 d . . . . .
N1 N 0.1364(4) 0.3928(3) 0.3917(2) 0.0320(7) Uani 1 1 d D . . . .
N2 N 0.0492(4) 0.5290(3) 0.2760(2) 0.0282(7) Uani 1 1 d . . . . .
N3 N -0.0555(3) 0.4273(3) 0.2054(2) 0.0263(6) Uani 1 1 d . . . . .
N4 N -0.0485(3) 0.6898(3) 0.1406(2) 0.0264(6) Uani 1 1 d . . . . .
N5 N -0.0609(4) 0.8056(3) 0.1117(2) 0.0290(7) Uani 1 1 d D . . . .
H5 H -0.149(4) 0.806(4) 0.064(3) 0.046(11) Uiso 1 1 d D . . . .
N6 N 0.1673(4) 0.9043(3) 0.2513(2) 0.0319(7) Uani 1 1 d . . . . .
H6 H 0.187(6) 0.834(4) 0.249(4) 0.051(14) Uiso 1 1 d . . . . .
C1 C 0.1999(5) 0.1488(3) 0.5686(3) 0.0348(9) Uani 1 1 d . . . . .
H1A H 0.3247 0.1672 0.5689 0.042 Uiso 1 1 calc R U . . .
H1B H 0.1267 0.0704 0.5939 0.042 Uiso 1 1 calc R U . . .
C2 C 0.1274(5) 0.2329(3) 0.5329(3) 0.0343(9) Uani 1 1 d . . . . .
H2A H 0.0021 0.2113 0.5339 0.041 Uiso 1 1 calc R U . . .
C3 C 0.2307(5) 0.3607(4) 0.4908(3) 0.0489(11) Uani 1 1 d . . . . .
H3A H 0.2516 0.4269 0.5492 0.059 Uiso 1 1 calc R U . . .
H3B H 0.3487 0.3607 0.4733 0.059 Uiso 1 1 calc R U . . .
C4 C 0.1472(4) 0.5130(3) 0.3713(3) 0.0277(8) Uani 1 1 d . . . . .
C5 C -0.1382(4) 0.4573(3) 0.1165(3) 0.0235(7) Uani 1 1 d . . . . .
C6 C -0.2565(4) 0.3595(3) 0.0333(2) 0.0229(7) Uani 1 1 d . . . . .
C7 C -0.3091(4) 0.2266(3) 0.0235(3) 0.0273(8) Uani 1 1 d . . . . .
H7 H -0.2660 0.1809 0.0767 0.033 Uiso 1 1 calc R U . . .
C8 C -0.4308(5) 0.1621(3) -0.0703(3) 0.0314(8) Uani 1 1 d . . . . .
H8 H -0.4678 0.0724 -0.0772 0.038 Uiso 1 1 calc R U . . .
C9 C -0.4967(4) 0.2257(3) -0.1515(3) 0.0302(8) Uani 1 1 d . . . . .
H9 H -0.5756 0.1792 -0.2119 0.036 Uiso 1 1 calc R U . . .
C10 C -0.4444(4) 0.3624(3) -0.1430(2) 0.0253(7) Uani 1 1 d . . . . .
C11 C -0.5011(4) 0.4432(3) -0.2177(3) 0.0290(8) Uani 1 1 d . . . . .
H11 H -0.5817 0.4067 -0.2806 0.035 Uiso 1 1 calc R U . . .
C12 C -0.4375(4) 0.5748(3) -0.1975(3) 0.0291(8) Uani 1 1 d . . . . .
H12 H -0.4746 0.6256 -0.2486 0.035 Uiso 1 1 calc R U . . .
C13 C -0.3175(4) 0.6364(3) -0.1018(3) 0.0274(8) Uani 1 1 d . . . . .
H13 H -0.2779 0.7257 -0.0901 0.033 Uiso 1 1 calc R U . . .
C14 C -0.2608(4) 0.5612(3) -0.0267(2) 0.0245(7) Uani 1 1 d . . . . .
C15 C -0.3258(4) 0.4255(3) -0.0489(2) 0.0238(7) Uani 1 1 d . . . . .
C16 C -0.1405(4) 0.5861(3) 0.0797(2) 0.0242(7) Uani 1 1 d . . . . .
C17 C 0.0377(4) 0.9153(3) 0.1770(3) 0.0305(8) Uani 1 1 d . . . . .
C18 C 0.2871(5) 1.0094(4) 0.3278(3) 0.0377(9) Uani 1 1 d . . . . .
H18A H 0.3251 0.9726 0.3943 0.045 Uiso 1 1 calc R U . . .
H18B H 0.2189 1.0622 0.3502 0.045 Uiso 1 1 calc R U . . .
C19 C 0.4521(5) 1.0931(3) 0.2784(3) 0.0372(9) Uani 1 1 d . . . . .
H19 H 0.4350 1.1266 0.2094 0.045 Uiso 1 1 calc R U . . .
C20 C 0.6208(5) 1.1231(4) 0.3254(3) 0.0432(10) Uani 1 1 d . . . . .
H20A H 0.6429 1.0913 0.3944 0.052 Uiso 1 1 calc R U . . .
H20B H 0.7176 1.1761 0.2897 0.052 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 C4 1.678(4) . ?
S2 C17 1.674(4) . ?
N1 C4 1.327(5) . ?
N1 C3 1.458(4) . ?
N1 H1 0.838(19) . ?
N2 N3 1.367(4) . ?
N2 C4 1.370(4) . ?
N2 H2 0.81(4) . ?
N3 C5 1.306(4) . ?
N4 C16 1.297(4) . ?
N4 N5 1.361(4) . ?
N5 C17 1.380(4) . ?
N5 H5 0.855(19) . ?
N6 C17 1.331(4) . ?
N6 C18 1.463(4) . ?
N6 H6 0.85(5) . ?
C1 C2 1.304(5) . ?
C1 H1A 0.9300 . ?
C1 H1B 0.9300 . ?
C2 C3 1.484(5) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C6 1.464(4) . ?
C5 C16 1.500(4) . ?
C6 C7 1.380(5) . ?
C6 C15 1.413(4) . ?
C7 C8 1.417(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.375(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.420(5) . ?
C9 H9 0.9300 . ?
C10 C15 1.405(4) . ?
C10 C11 1.422(4) . ?
C11 C12 1.373(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.420(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.419(5) . ?
C14 C16 1.483(4) . ?
C18 C19 1.488(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.319(5) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9300 . ?
C20 H20B 0.9300 . ?

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
C4 N1 C3 122.6(3) . . ?
C4 N1 H1 119(3) . . ?
C3 N1 H1 118(3) . . ?
N3 N2 C4 122.3(3) . . ?
N3 N2 H2 117(3) . . ?
C4 N2 H2 120(3) . . ?
C5 N3 N2 115.6(3) . . ?
C16 N4 N5 119.9(3) . . ?
N4 N5 C17 119.4(3) . . ?
N4 N5 H5 118(3) . . ?
C17 N5 H5 120(3) . . ?
C17 N6 C18 124.3(3) . . ?
C17 N6 H6 117(3) . . ?
C18 N6 H6 118(3) . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C1 C2 C3 124.6(3) . . ?
C1 C2 H2A 117.7 . . ?
C3 C2 H2A 117.7 . . ?
N1 C3 C2 112.8(3) . . ?
N1 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
N1 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
N1 C4 N2 116.4(3) . . ?
N1 C4 S1 126.0(2) . . ?
N2 C4 S1 117.6(3) . . ?
N3 C5 C6 122.3(3) . . ?
N3 C5 C16 130.3(3) . . ?
C6 C5 C16 107.3(2) . . ?
C7 C6 C15 119.4(3) . . ?
C7 C6 C5 133.6(3) . . ?
C15 C6 C5 106.9(3) . . ?
C6 C7 C8 117.9(3) . . ?
C6 C7 H7 121.1 . . ?
C8 C7 H7 121.1 . . ?
C9 C8 C7 123.1(3) . . ?
C9 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
C8 C9 C10 119.9(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C15 C10 C9 116.6(3) . . ?
C15 C10 C11 115.9(3) . . ?
C9 C10 C11 127.5(3) . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 122.7(3) . . ?
C11 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C14 C13 C12 118.7(3) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C13 C14 C15 118.2(3) . . ?
C13 C14 C16 135.5(3) . . ?
C15 C14 C16 106.4(3) . . ?
C10 C15 C6 123.1(3) . . ?
C10 C15 C14 124.1(3) . . ?
C6 C15 C14 112.8(3) . . ?
N4 C16 C14 133.6(3) . . ?
N4 C16 C5 119.8(3) . . ?
C14 C16 C5 106.6(3) . . ?
N6 C17 N5 115.9(3) . . ?
N6 C17 S2 125.3(3) . . ?
N5 C17 S2 118.8(2) . . ?
N6 C18 C19 113.3(3) . . ?
N6 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
N6 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 124.7(3) . . ?
C20 C19 H19 117.7 . . ?
C18 C19 H19 117.7 . . ?
C19 C20 H20A 120.0 . . ?
C19 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?

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
N2 H2 N4 0.81(4) 2.00(4) 2.677(4) 141(4) .

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_Ga(3)
_database_code_depnum_ccdc_archive 'CCDC 1001634'
_audit_update_record             
;
2014-05-07 deposited with the CCDC.
2015-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Cl Ga N6 S2, 2(C2 H6 O S)'
_chemical_formula_sum            'C22 H30 Cl Ga N6 O2 S4'
_chemical_formula_weight         643.93

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'
Ga Ga 0.2307 1.6083 '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'
O O 0.0106 0.0060 '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                   11.55230(10)
_cell_length_b                   11.7595(3)
_cell_length_c                   12.0749(3)
_cell_angle_alpha                114.468(2)
_cell_angle_beta                 105.4834(17)
_cell_angle_gamma                93.4737(18)
_cell_volume                     1411.20(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    15626
_cell_measurement_theta_min      2.9289
_cell_measurement_theta_max      37.0716

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    1.397
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.78016
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;

;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector_area_resol_mean 10.3795
_diffrn_measurement_method       'ω and π scans'
_diffrn_reflns_number            50963
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.535
_diffrn_reflns_theta_max         37.159
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             12291
_reflns_number_gt                9078
_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       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec  8 2009,17:31:18)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec  8 2009,17:31:18)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec  8 2009,17:31:18)
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;

_refine_special_details          
;
  one solvent molecule is disordered over two sites in the ratio 80:20
  hetero atom hydrogen atoms have been freely refined.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+0.8682P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12291
_refine_ls_number_parameters     356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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_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
Ga Ga 0.14221(2) 0.23791(2) 0.72491(2) 0.02323(5) Uani 1 1 d . . . . .
Cl Cl 0.28834(5) 0.41096(5) 0.83750(5) 0.03662(11) Uani 1 1 d . . . . .
N1 N 0.30543(15) -0.05786(15) 0.67085(15) 0.0246(3) Uani 1 1 d . . . . .
H1 H 0.315(2) -0.075(3) 0.728(3) 0.037(7) Uiso 1 1 d . . . . .
N2 N 0.20119(15) 0.10293(15) 0.76634(14) 0.0241(3) Uani 1 1 d . . . . .
N3 N 0.21357(14) 0.07230(14) 0.86518(14) 0.0225(3) Uani 1 1 d . . . . .
N4 N 0.04689(14) 0.26182(14) 0.85026(14) 0.0227(3) Uani 1 1 d . . . . .
N5 N -0.04263(15) 0.33107(14) 0.84963(15) 0.0251(3) Uani 1 1 d . . . . .
N6 N -0.16993(16) 0.40942(16) 0.73123(17) 0.0291(3) Uani 1 1 d . . . . .
H6A H -0.202(2) 0.413(3) 0.666(3) 0.034(7) Uiso 1 1 d . . . . .
S1 S 0.22673(5) 0.09537(5) 0.56114(5) 0.03129(11) Uani 1 1 d . . . . .
S2 S -0.02631(5) 0.27919(5) 0.61024(5) 0.03072(10) Uani 1 1 d . . . . .
C1 C 0.4975(2) -0.0610(3) 0.6191(2) 0.0420(5) Uani 1 1 d . . . . .
H1A H 0.5321 -0.1013 0.5497 0.063 Uiso 1 1 calc R U . . .
H1B H 0.5425 -0.0720 0.6941 0.063 Uiso 1 1 calc R U . . .
H1C H 0.5044 0.0301 0.6424 0.063 Uiso 1 1 calc R U . . .
C2 C 0.36425(19) -0.12224(19) 0.57477(18) 0.0300(4) Uani 1 1 d . . . . .
H2A H 0.3209 -0.1194 0.4936 0.036 Uiso 1 1 calc R U . . .
H2B H 0.3579 -0.2128 0.5574 0.036 Uiso 1 1 calc R U . . .
C3 C 0.24941(17) 0.03663(17) 0.67351(16) 0.0232(3) Uani 1 1 d . . . . .
C4 C 0.15633(16) 0.13317(16) 0.94474(15) 0.0214(3) Uani 1 1 d . . . . .
C5 C 0.15187(16) 0.10688(16) 1.05271(15) 0.0215(3) Uani 1 1 d . . . . .
C6 C 0.20460(17) 0.02811(18) 1.10085(17) 0.0262(3) Uani 1 1 d . . . . .
H6 H 0.2619 -0.0182 1.0674 0.031 Uiso 1 1 calc R U . . .
C7 C 0.17141(18) 0.01771(19) 1.20157(18) 0.0290(4) Uani 1 1 d . . . . .
H7 H 0.2080 -0.0359 1.2359 0.035 Uiso 1 1 calc R U . . .
C8 C 0.08775(18) 0.08288(19) 1.25133(17) 0.0287(4) Uani 1 1 d . . . . .
H8 H 0.0673 0.0730 1.3184 0.034 Uiso 1 1 calc R U . . .
C9 C 0.03199(17) 0.16453(18) 1.20343(16) 0.0250(3) Uani 1 1 d . . . . .
C10 C -0.0591(2) 0.2341(2) 1.24017(18) 0.0316(4) Uani 1 1 d . . . . .
H10 H -0.0877 0.2304 1.3056 0.038 Uiso 1 1 calc R U . . .
C11 C -0.1056(2) 0.3069(2) 1.18059(19) 0.0325(4) Uani 1 1 d . . . . .
H11 H -0.1652 0.3538 1.2078 0.039 Uiso 1 1 calc R U . . .
C12 C -0.06907(19) 0.31523(19) 1.08073(18) 0.0285(4) Uani 1 1 d . . . . .
H12 H -0.1031 0.3663 1.0417 0.034 Uiso 1 1 calc R U . . .
C13 C 0.01741(16) 0.24691(16) 1.04205(16) 0.0225(3) Uani 1 1 d . . . . .
C14 C 0.06764(16) 0.17482(16) 1.10541(15) 0.0215(3) Uani 1 1 d . . . . .
C15 C 0.07226(16) 0.22298(15) 0.93958(15) 0.0209(3) Uani 1 1 d . . . . .
C16 C -0.08086(17) 0.34452(16) 0.74200(17) 0.0238(3) Uani 1 1 d . . . . .
C17 C -0.2327(2) 0.4579(2) 0.8266(2) 0.0334(4) Uani 1 1 d . . . . .
H17A H -0.2614 0.5354 0.8263 0.040 Uiso 1 1 calc R U . . .
H17B H -0.1743 0.4819 0.9130 0.040 Uiso 1 1 calc R U . . .
C18 C -0.3402(3) 0.3610(3) 0.8003(3) 0.0468(6) Uani 1 1 d . . . . .
H18A H -0.3989 0.3380 0.7154 0.070 Uiso 1 1 calc R U . . .
H18B H -0.3800 0.3970 0.8660 0.070 Uiso 1 1 calc R U . . .
H18C H -0.3119 0.2848 0.8023 0.070 Uiso 1 1 calc R U . . .
S3 S 0.50267(6) 0.18043(6) 0.09091(6) 0.03289(17) Uani 0.849(2) 1 d . . P A 1
O1 O 0.6204(3) 0.2028(3) 0.1952(4) 0.0408(6) Uani 0.849(2) 1 d . . P A 1
S3A S 0.5801(3) 0.2639(4) 0.1327(4) 0.0364(10) Uani 0.151(2) 1 d . . P A 2
O1A O 0.5772(19) 0.161(2) 0.170(2) 0.056(5) Uani 0.151(2) 1 d . . P A 2
C21 C 0.4483(2) 0.3262(3) 0.1398(2) 0.0469(6) Uani 1 1 d . . . . .
H21A H 0.5140 0.3963 0.1621 0.070 Uiso 0.849(2) 1 calc R U P A 1
H21B H 0.4224 0.3415 0.2149 0.070 Uiso 0.849(2) 1 calc R U P A 1
H21C H 0.3786 0.3209 0.0694 0.070 Uiso 0.849(2) 1 calc R U P A 1
H21D H 0.4666 0.4175 0.1642 0.070 Uiso 0.151(2) 1 calc R U P A 2
H21E H 0.4191 0.3136 0.2038 0.070 Uiso 0.151(2) 1 calc R U P A 2
H21F H 0.3849 0.2826 0.0554 0.070 Uiso 0.151(2) 1 calc R U P A 2
C22 C 0.5432(3) 0.1911(4) -0.0358(3) 0.0607(9) Uani 1 1 d . . . . .
H22A H 0.5739 0.1149 -0.0806 0.091 Uiso 0.849(2) 1 calc R U P A 1
H22B H 0.6072 0.2668 -0.0010 0.091 Uiso 0.849(2) 1 calc R U P A 1
H22C H 0.4711 0.1976 -0.0962 0.091 Uiso 0.849(2) 1 calc R U P A 1
H22D H 0.5819 0.1167 -0.0629 0.091 Uiso 0.151(2) 1 calc R U P A 2
H22E H 0.5731 0.2521 -0.0627 0.091 Uiso 0.151(2) 1 calc R U P A 2
H22F H 0.4542 0.1641 -0.0757 0.091 Uiso 0.151(2) 1 calc R U P A 2
S4 S 0.34195(6) 0.49882(5) 0.54192(5) 0.04606(16) Uani 1 1 d . . . . .
O2 O 0.34909(16) 0.5470(2) 0.4477(2) 0.0532(5) Uani 1 1 d . . . . .
C23 C 0.3532(3) 0.3378(3) 0.4749(4) 0.0665(10) Uani 1 1 d . . . . .
H23A H 0.2932 0.2927 0.3886 0.100 Uiso 1 1 calc R U . . .
H23B H 0.3367 0.2999 0.5291 0.100 Uiso 1 1 calc R U . . .
H23C H 0.4358 0.3307 0.4697 0.100 Uiso 1 1 calc R U . . .
C24 C 0.1839(3) 0.4785(3) 0.5305(3) 0.0616(8) Uani 1 1 d . . . . .
H24A H 0.1337 0.4270 0.4405 0.092 Uiso 1 1 calc R U . . .
H24B H 0.1607 0.5621 0.5634 0.092 Uiso 1 1 calc R U . . .
H24C H 0.1707 0.4353 0.5815 0.092 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
Ga N2 1.9599(14) . ?
Ga N4 2.0390(15) . ?
Ga Cl 2.2149(6) . ?
Ga S2 2.2748(5) . ?
Ga S1 2.4813(5) . ?
N1 C3 1.313(2) . ?
N1 C2 1.462(2) . ?
N1 H1 0.78(3) . ?
N2 C3 1.355(2) . ?
N2 N3 1.3586(19) . ?
N3 C4 1.304(2) . ?
N4 C15 1.309(2) . ?
N4 N5 1.355(2) . ?
N5 C16 1.335(2) . ?
N6 C16 1.328(2) . ?
N6 C17 1.459(3) . ?
N6 H6A 0.80(3) . ?
S1 C3 1.7308(17) . ?
S2 C16 1.7606(19) . ?
C1 C2 1.511(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 C5 1.472(2) . ?
C4 C15 1.486(2) . ?
C5 C6 1.376(2) . ?
C5 C14 1.412(3) . ?
C6 C7 1.417(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.417(3) . ?
C8 H8 0.9500 . ?
C9 C14 1.399(2) . ?
C9 C10 1.424(3) . ?
C10 C11 1.378(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.417(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.414(2) . ?
C13 C15 1.471(2) . ?
C17 C18 1.504(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
S3 O1 1.508(3) . ?
S3 C22 1.764(3) . ?
S3 C21 1.781(2) . ?
S3A O1A 1.449(18) . ?
S3A C21 1.737(4) . ?
S3A C22 1.762(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 H21D 0.9800 . ?
C21 H21E 0.9800 . ?
C21 H21F 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 H22D 0.9800 . ?
C22 H22E 0.9800 . ?
C22 H22F 0.9800 . ?
S4 O2 1.4838(18) . ?
S4 C23 1.753(3) . ?
S4 C24 1.787(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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 Ga N4 86.39(6) . . ?
N2 Ga Cl 107.73(5) . . ?
N4 Ga Cl 100.70(5) . . ?
N2 Ga S2 141.64(5) . . ?
N4 Ga S2 83.98(4) . . ?
Cl Ga S2 110.52(2) . . ?
N2 Ga S1 68.57(5) . . ?
N4 Ga S1 149.58(4) . . ?
Cl Ga S1 103.17(2) . . ?
S2 Ga S1 104.713(19) . . ?
C3 N1 C2 123.39(15) . . ?
C3 N1 H1 118(2) . . ?
C2 N1 H1 118(2) . . ?
C3 N2 N3 118.37(14) . . ?
C3 N2 Ga 105.20(11) . . ?
N3 N2 Ga 136.08(12) . . ?
C4 N3 N2 114.59(14) . . ?
C15 N4 N5 116.57(15) . . ?
C15 N4 Ga 124.34(12) . . ?
N5 N4 Ga 118.87(11) . . ?
C16 N5 N4 112.99(15) . . ?
C16 N6 C17 123.10(16) . . ?
C16 N6 H6A 121.3(19) . . ?
C17 N6 H6A 114.5(19) . . ?
C3 S1 Ga 75.97(6) . . ?
C16 S2 Ga 93.16(6) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 111.63(17) . . ?
N1 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N1 C3 N2 124.32(15) . . ?
N1 C3 S1 125.57(14) . . ?
N2 C3 S1 110.11(12) . . ?
N3 C4 C5 122.65(15) . . ?
N3 C4 C15 130.53(14) . . ?
C5 C4 C15 106.30(15) . . ?
C6 C5 C14 119.20(16) . . ?
C6 C5 C4 133.44(17) . . ?
C14 C5 C4 107.20(14) . . ?
C5 C6 C7 118.41(18) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C8 C7 C6 122.09(16) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C9 120.65(16) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C14 C9 C8 116.22(17) . . ?
C14 C9 C10 116.04(16) . . ?
C8 C9 C10 127.70(17) . . ?
C11 C10 C9 119.84(18) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 123.27(19) . . ?
C10 C11 H11 118.4 . . ?
C12 C11 H11 118.4 . . ?
C13 C12 C11 117.89(17) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C12 C13 C14 118.91(16) . . ?
C12 C13 C15 134.81(16) . . ?
C14 C13 C15 106.21(15) . . ?
C9 C14 C5 123.40(15) . . ?
C9 C14 C13 124.00(17) . . ?
C5 C14 C13 112.45(15) . . ?
N4 C15 C13 128.24(15) . . ?
N4 C15 C4 123.68(16) . . ?
C13 C15 C4 107.82(13) . . ?
N6 C16 N5 117.60(17) . . ?
N6 C16 S2 116.91(13) . . ?
N5 C16 S2 125.45(13) . . ?
N6 C17 C18 111.87(19) . . ?
N6 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
N6 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 S3 C22 106.95(18) . . ?
O1 S3 C21 106.28(16) . . ?
C22 S3 C21 95.50(15) . . ?
O1A S3A C21 108.9(11) . . ?
O1A S3A C22 106.3(10) . . ?
C21 S3A C22 97.2(2) . . ?
S3 C21 H21A 109.5 . . ?
S3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S3A C21 H21D 109.5 . . ?
S3A C21 H21E 109.5 . . ?
H21D C21 H21E 109.5 . . ?
S3A C21 H21F 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
S3 C22 H22A 109.5 . . ?
S3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
S3A C22 H22D 109.5 . . ?
S3A C22 H22E 109.5 . . ?
H22D C22 H22E 109.5 . . ?
S3A C22 H22F 109.5 . . ?
H22D C22 H22F 109.5 . . ?
H22E C22 H22F 109.5 . . ?
O2 S4 C23 107.51(17) . . ?
O2 S4 C24 105.25(12) . . ?
C23 S4 C24 98.39(15) . . ?
S4 C23 H23A 109.5 . . ?
S4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
S4 C24 H24A 109.5 . . ?
S4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
S4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C3 N2 N3 C4 -174.70(16) . . . . ?
Ga N2 N3 C4 13.3(3) . . . . ?
C15 N4 N5 C16 -166.88(16) . . . . ?
Ga N4 N5 C16 18.3(2) . . . . ?
C3 N1 C2 C1 91.1(2) . . . . ?
C2 N1 C3 N2 -175.57(18) . . . . ?
C2 N1 C3 S1 4.1(3) . . . . ?
N3 N2 C3 N1 1.6(3) . . . . ?
Ga N2 C3 N1 175.84(16) . . . . ?
N3 N2 C3 S1 -178.14(13) . . . . ?
Ga N2 C3 S1 -3.87(15) . . . . ?
Ga S1 C3 N1 -176.67(18) . . . . ?
Ga S1 C3 N2 3.04(12) . . . . ?
N2 N3 C4 C5 175.77(15) . . . . ?
N2 N3 C4 C15 5.3(3) . . . . ?
N3 C4 C5 C6 4.2(3) . . . . ?
C15 C4 C5 C6 176.64(19) . . . . ?
N3 C4 C5 C14 -171.05(16) . . . . ?
C15 C4 C5 C14 1.41(18) . . . . ?
C14 C5 C6 C7 0.4(3) . . . . ?
C4 C5 C6 C7 -174.40(18) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 C14 -0.5(3) . . . . ?
C7 C8 C9 C10 177.22(19) . . . . ?
C14 C9 C10 C11 -0.6(3) . . . . ?
C8 C9 C10 C11 -178.3(2) . . . . ?
C9 C10 C11 C12 1.2(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 -1.6(3) . . . . ?
C11 C12 C13 C15 175.01(19) . . . . ?
C8 C9 C14 C5 1.5(3) . . . . ?
C10 C9 C14 C5 -176.49(17) . . . . ?
C8 C9 C14 C13 176.86(16) . . . . ?
C10 C9 C14 C13 -1.1(3) . . . . ?
C6 C5 C14 C9 -1.5(3) . . . . ?
C4 C5 C14 C9 174.58(16) . . . . ?
C6 C5 C14 C13 -177.32(16) . . . . ?
C4 C5 C14 C13 -1.3(2) . . . . ?
C12 C13 C14 C9 2.3(3) . . . . ?
C15 C13 C14 C9 -175.23(16) . . . . ?
C12 C13 C14 C5 178.09(16) . . . . ?
C15 C13 C14 C5 0.59(19) . . . . ?
N5 N4 C15 C13 -1.3(3) . . . . ?
Ga N4 C15 C13 173.22(13) . . . . ?
N5 N4 C15 C4 172.15(15) . . . . ?
Ga N4 C15 C4 -13.3(2) . . . . ?
C12 C13 C15 N4 -2.3(3) . . . . ?
C14 C13 C15 N4 174.61(17) . . . . ?
C12 C13 C15 C4 -176.6(2) . . . . ?
C14 C13 C15 C4 0.33(18) . . . . ?
N3 C4 C15 N4 -4.0(3) . . . . ?
C5 C4 C15 N4 -175.67(16) . . . . ?
N3 C4 C15 C13 170.57(18) . . . . ?
C5 C4 C15 C13 -1.07(18) . . . . ?
C17 N6 C16 N5 -4.5(3) . . . . ?
C17 N6 C16 S2 173.62(16) . . . . ?
N4 N5 C16 N6 179.02(16) . . . . ?
N4 N5 C16 S2 1.1(2) . . . . ?
Ga S2 C16 N6 166.39(14) . . . . ?
Ga S2 C16 N5 -15.64(16) . . . . ?
C16 N6 C17 C18 -87.7(3) . . . . ?
O1A S3A C21 S3 -41.8(10) . . . . ?
C22 S3A C21 S3 68.3(2) . . . . ?
O1 S3 C21 S3A 41.8(3) . . . . ?
C22 S3 C21 S3A -67.6(3) . . . . ?
O1A S3A C22 S3 42.2(10) . . . . ?
C21 S3A C22 S3 -69.9(2) . . . . ?
O1 S3 C22 S3A -43.0(2) . . . . ?
C21 S3 C22 S3A 65.9(2) . . . . ?

_refine_diff_density_max         1.746
_refine_diff_density_min         -0.884
_refine_diff_density_rms         0.086

_shelxl_version_number           2013-4

