# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 S4'
_chemical_formula_sum            'C14 H17 N3 S4'
_chemical_formula_weight         355.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   'P 21/c'

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

_cell_length_a                   5.3381(5)
_cell_length_b                   25.8440(19)
_cell_length_c                   11.0690(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.555(7)
_cell_angle_gamma                90.00
_cell_volume                     1505.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3380
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      27.50

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5952
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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_type  area_detector
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17019
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_sigmaI/netI    0.0712
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3380
_reflns_number_gt                1964
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       KappaCCD
_computing_cell_refinement       'Dirax/1sq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0905P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3380
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1640
_refine_ls_wR_factor_gt          0.1453
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.37379(18) 0.53819(3) 0.87365(10) 0.0522(3) Uani 1 1 d . . .
S2 S 0.09653(18) 0.58150(4) 0.65000(9) 0.0528(3) Uani 1 1 d . . .
S3 S 0.77278(17) 0.62478(3) 0.90574(9) 0.0492(3) Uani 1 1 d . . .
S4 S 0.47950(18) 0.66895(3) 0.68561(9) 0.0476(3) Uani 1 1 d . . .
N1 N 1.2154(5) 0.73854(10) 0.9412(3) 0.0455(7) Uani 1 1 d . . .
N2 N 1.4187(6) 0.74139(12) 1.0310(3) 0.0544(8) Uani 1 1 d . . .
N3 N 1.4395(6) 0.70238(14) 1.0913(3) 0.0604(9) Uani 1 1 d . . .
C1 C 0.1050(7) 0.50847(12) 0.7964(4) 0.0455(9) Uani 1 1 d . . .
C2 C -0.0193(7) 0.52837(13) 0.6957(4) 0.0473(9) Uani 1 1 d . . .
C3 C 0.3509(6) 0.58542(12) 0.7722(3) 0.0419(8) Uani 1 1 d . . .
C4 C 0.5123(6) 0.62141(12) 0.7863(3) 0.0389(8) Uani 1 1 d . . .
C5 C 0.8757(6) 0.67923(11) 0.8633(3) 0.0379(8) Uani 1 1 d . . .
C6 C 0.7398(7) 0.69859(13) 0.7631(3) 0.0460(9) Uani 1 1 d . . .
H6 H 0.7896 0.7300 0.7336 0.055 Uiso 1 1 calc R . .
C7 C 1.1012(6) 0.69638(12) 0.9442(3) 0.0398(8) Uani 1 1 d . . .
C8 C 1.2501(7) 0.67425(14) 1.0407(4) 0.0530(10) Uani 1 1 d . . .
H8 H 1.2191 0.6413 1.0687 0.064 Uiso 1 1 calc R . .
C9 C 0.0390(8) 0.46412(14) 0.8542(4) 0.0618(11) Uani 1 1 d . . .
H9A H 0.1617 0.4579 0.9266 0.093 Uiso 1 1 calc R . .
H9B H 0.0357 0.4352 0.7997 0.093 Uiso 1 1 calc R . .
H9C H -0.1259 0.4686 0.8765 0.093 Uiso 1 1 calc R . .
C10 C -0.2527(8) 0.50964(17) 0.6143(4) 0.0660(12) Uani 1 1 d . . .
H10A H -0.2961 0.5332 0.5469 0.099 Uiso 1 1 calc R . .
H10B H -0.3904 0.5078 0.6600 0.099 Uiso 1 1 calc R . .
H10C H -0.2218 0.4759 0.5835 0.099 Uiso 1 1 calc R . .
C11 C 1.1520(7) 0.77993(13) 0.8646(4) 0.0551(10) Uani 1 1 d . . .
H11A H 1.1091 0.7679 0.7807 0.066 Uiso 1 1 calc R . .
H11B H 1.2959 0.8032 0.8695 0.066 Uiso 1 1 calc R . .
C12 C 0.9323(7) 0.80785(13) 0.8999(4) 0.0540(10) Uani 1 1 d . . .
H12A H 0.7815 0.7863 0.8845 0.065 Uiso 1 1 calc R . .
H12B H 0.9663 0.8163 0.9865 0.065 Uiso 1 1 calc R . .
C13 C 0.8949(7) 0.85301(14) 0.8301(4) 0.0632(11) Uani 1 1 d . . .
H13A H 0.8738 0.8442 0.7438 0.076 Uiso 1 1 calc R . .
H13B H 1.0436 0.8750 0.8493 0.076 Uiso 1 1 calc R . .
C14 C 0.6718(8) 0.88117(16) 0.8541(5) 0.0707(13) Uani 1 1 d . . .
H14A H 0.6491 0.9117 0.8040 0.106 Uiso 1 1 calc R . .
H14B H 0.6949 0.8909 0.9389 0.106 Uiso 1 1 calc R . .
H14C H 0.5246 0.8595 0.8353 0.106 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 C3 1.650(3) . ?
S1 C1 1.724(4) . ?
S2 C2 1.621(4) . ?
S2 C3 1.753(4) . ?
S3 C5 1.609(3) . ?
S3 C4 1.755(4) . ?
S4 C4 1.648(3) . ?
S4 C6 1.690(4) . ?
N1 C7 1.252(4) . ?
N1 N2 1.347(4) . ?
N1 C11 1.372(4) . ?
N2 N3 1.204(4) . ?
N2 C8 1.966(5) . ?
N3 C8 1.295(5) . ?
C1 C2 1.304(5) . ?
C1 C9 1.387(5) . ?
C2 C10 1.492(5) . ?
C3 C4 1.260(4) . ?
C5 C6 1.319(5) . ?
C5 C7 1.446(5) . ?
C7 C8 1.348(5) . ?
C11 C12 1.484(5) . ?
C12 C13 1.396(5) . ?
C13 C14 1.457(5) . ?

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
C3 S1 C1 91.74(18) . . ?
C2 S2 C3 95.45(18) . . ?
C5 S3 C4 95.14(16) . . ?
C4 S4 C6 90.51(17) . . ?
C7 N1 N2 111.4(3) . . ?
C7 N1 C11 128.6(3) . . ?
N2 N1 C11 120.0(3) . . ?
N3 N2 N1 110.6(3) . . ?
N3 N2 C8 39.8(2) . . ?
N1 N2 C8 70.8(2) . . ?
N2 N3 C8 103.7(3) . . ?
C2 C1 C9 126.0(4) . . ?
C2 C1 S1 120.8(3) . . ?
C9 C1 S1 113.2(3) . . ?
C1 C2 C10 130.1(4) . . ?
C1 C2 S2 115.7(3) . . ?
C10 C2 S2 114.2(3) . . ?
C4 C3 S1 119.3(3) . . ?
C4 C3 S2 124.4(3) . . ?
S1 C3 S2 116.30(19) . . ?
C3 C4 S4 118.2(3) . . ?
C3 C4 S3 124.8(3) . . ?
S4 C4 S3 117.02(18) . . ?
C6 C5 C7 133.6(3) . . ?
C6 C5 S3 114.3(3) . . ?
C7 C5 S3 112.1(2) . . ?
C5 C6 S4 123.1(3) . . ?
N1 C7 C8 99.5(3) . . ?
N1 C7 C5 127.6(3) . . ?
C8 C7 C5 133.0(3) . . ?
N3 C8 C7 114.8(4) . . ?
N3 C8 N2 36.5(2) . . ?
C7 C8 N2 78.3(2) . . ?
N1 C11 C12 109.9(3) . . ?
C13 C12 C11 107.9(3) . . ?
C12 C13 C14 111.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.076
_database_code_depnum_ccdc_archive 'CCDC 982420'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 S4 Si2'
_chemical_formula_sum            'C18 H24 S4 Si2'
_chemical_formula_weight         424.79

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'
Si Si 0.0817 0.0704 '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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3081(14)
_cell_length_b                   8.1474(16)
_cell_length_c                   22.670(5)
_cell_angle_alpha                94.79(3)
_cell_angle_beta                 96.73(2)
_cell_angle_gamma                92.57(2)
_cell_volume                     1151.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3148
_cell_measurement_theta_min      3.87
_cell_measurement_theta_max      22.99

_exptl_crystal_description       sheet
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6851
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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_type  area_detector
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12528
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_av_sigmaI/netI    0.0768
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.87
_diffrn_reflns_theta_max         22.99
_reflns_number_total             3148
_reflns_number_gt                1929
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       KappaCCD
_computing_cell_refinement       'Dirax/1sq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0233P)²+1.7345P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3148
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.5275(3) -0.2973(2) 0.79575(7) 0.0522(5) Uani 1 1 d . . .
Si2 Si 1.3027(3) 0.2249(2) 0.90726(6) 0.0538(5) Uani 1 1 d . . .
S1 S 0.7779(2) 0.15652(18) 0.49008(6) 0.0485(4) Uani 1 1 d . . .
S2 S 0.6880(2) 0.12333(19) 0.62666(6) 0.0519(4) Uani 1 1 d . . .
S3 S 1.1886(2) 0.33683(18) 0.53189(6) 0.0504(4) Uani 1 1 d . . .
S4 S 1.0921(2) 0.31498(19) 0.66979(6) 0.0534(4) Uani 1 1 d . . .
C1 C 0.9376(9) 0.2115(7) 0.4355(2) 0.0437(14) Uani 1 1 d . . .
C2 C 1.1244(8) 0.2935(6) 0.4546(2) 0.0419(13) Uani 1 1 d . . .
C3 C 0.9568(8) 0.2367(6) 0.5511(2) 0.0389(13) Uani 1 1 d . . .
C4 C 0.9178(8) 0.2257(6) 0.6075(2) 0.0405(13) Uani 1 1 d . . .
C5 C 0.8031(8) 0.1006(6) 0.7002(2) 0.0400(13) Uani 1 1 d . . .
C6 C 0.9832(8) 0.1909(6) 0.7202(2) 0.0381(13) Uani 1 1 d . . .
C7 C 0.8406(9) 0.1682(8) 0.3718(2) 0.0640(18) Uani 1 1 d . . .
H7A H 0.7048 0.1095 0.3712 0.096 Uiso 1 1 calc R . .
H7B H 0.9342 0.0999 0.3514 0.096 Uiso 1 1 calc R . .
H7C H 0.8210 0.2674 0.3523 0.096 Uiso 1 1 calc R . .
C8 C 1.2836(9) 0.3603(8) 0.4170(2) 0.0641(18) Uani 1 1 d . . .
H8A H 1.4038 0.4137 0.4424 0.096 Uiso 1 1 calc R . .
H8B H 1.2175 0.4385 0.3923 0.096 Uiso 1 1 calc R . .
H8C H 1.3312 0.2713 0.3922 0.096 Uiso 1 1 calc R . .
C9 C 0.7008(8) -0.0155(7) 0.7329(2) 0.0451(14) Uani 1 1 d . . .
C10 C 0.6235(9) -0.1217(8) 0.7583(2) 0.0603(17) Uani 1 1 d . . .
C11 C 1.0889(9) 0.1996(6) 0.7797(2) 0.0464(14) Uani 1 1 d . . .
C12 C 1.1764(9) 0.2096(7) 0.8300(2) 0.0529(15) Uani 1 1 d . . .
C13 C 0.6045(10) -0.4884(8) 0.7557(3) 0.081(2) Uani 1 1 d . . .
H13A H 0.5559 -0.5822 0.7743 0.121 Uiso 1 1 calc R . .
H13B H 0.7573 -0.4866 0.7569 0.121 Uiso 1 1 calc R . .
H13C H 0.5404 -0.4955 0.7149 0.121 Uiso 1 1 calc R . .
C14 C 0.2319(9) -0.2948(8) 0.7943(3) 0.0708(18) Uani 1 1 d . . .
H14A H 0.1813 -0.3861 0.8140 0.106 Uiso 1 1 calc R . .
H14B H 0.1660 -0.3035 0.7537 0.106 Uiso 1 1 calc R . .
H14C H 0.1958 -0.1934 0.8145 0.106 Uiso 1 1 calc R . .
C15 C 0.6631(10) -0.2731(8) 0.8738(2) 0.078(2) Uani 1 1 d . . .
H15A H 0.6163 -0.3626 0.8950 0.117 Uiso 1 1 calc R . .
H15B H 0.6279 -0.1705 0.8933 0.117 Uiso 1 1 calc R . .
H15C H 0.8151 -0.2738 0.8734 0.117 Uiso 1 1 calc R . .
C16 C 1.2091(11) 0.0438(8) 0.9428(3) 0.084(2) Uani 1 1 d . . .
H16A H 1.2750 0.0495 0.9833 0.126 Uiso 1 1 calc R . .
H16B H 1.2471 -0.0551 0.9214 0.126 Uiso 1 1 calc R . .
H16C H 1.0566 0.0429 0.9421 0.126 Uiso 1 1 calc R . .
C17 C 1.2189(10) 0.4162(8) 0.9461(3) 0.084(2) Uani 1 1 d . . .
H17A H 1.2836 0.4267 0.9868 0.125 Uiso 1 1 calc R . .
H17B H 1.0661 0.4111 0.9449 0.125 Uiso 1 1 calc R . .
H17C H 1.2636 0.5097 0.9266 0.125 Uiso 1 1 calc R . .
C18 C 1.5962(9) 0.2305(8) 0.9068(3) 0.0760(19) Uani 1 1 d . . .
H18A H 1.6652 0.2376 0.9471 0.114 Uiso 1 1 calc R . .
H18B H 1.6409 0.3249 0.8878 0.114 Uiso 1 1 calc R . .
H18C H 1.6348 0.1319 0.8854 0.114 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
Si1 C10 1.839(6) . ?
Si1 C13 1.849(6) . ?
Si1 C14 1.863(6) . ?
Si1 C15 1.864(6) . ?
Si2 C12 1.828(6) . ?
Si2 C16 1.845(6) . ?
Si2 C18 1.851(6) . ?
Si2 C17 1.853(6) . ?
S1 C3 1.741(5) . ?
S1 C1 1.758(5) . ?
S2 C4 1.757(5) . ?
S2 C5 1.767(5) . ?
S3 C2 1.754(5) . ?
S3 C3 1.759(5) . ?
S4 C6 1.765(5) . ?
S4 C4 1.767(5) . ?
C1 C2 1.335(7) . ?
C1 C7 1.508(7) . ?
C2 C8 1.504(7) . ?
C3 C4 1.339(6) . ?
C5 C6 1.336(6) . ?
C5 C9 1.425(7) . ?
C6 C11 1.429(7) . ?
C9 C10 1.196(7) . ?
C11 C12 1.202(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 Si1 C13 107.8(3) . . ?
C10 Si1 C14 109.3(3) . . ?
C13 Si1 C14 111.1(3) . . ?
C10 Si1 C15 107.0(3) . . ?
C13 Si1 C15 110.5(3) . . ?
C14 Si1 C15 111.0(3) . . ?
C12 Si2 C16 108.4(3) . . ?
C12 Si2 C18 108.4(3) . . ?
C16 Si2 C18 111.0(3) . . ?
C12 Si2 C17 108.1(3) . . ?
C16 Si2 C17 109.8(3) . . ?
C18 Si2 C17 111.2(3) . . ?
C3 S1 C1 96.0(2) . . ?
C4 S2 C5 93.9(2) . . ?
C2 S3 C3 95.7(2) . . ?
C6 S4 C4 93.9(2) . . ?
C2 C1 C7 127.3(5) . . ?
C2 C1 S1 117.1(4) . . ?
C7 C1 S1 115.5(4) . . ?
C1 C2 C8 127.2(5) . . ?
C1 C2 S3 117.1(4) . . ?
C8 C2 S3 115.7(4) . . ?
C4 C3 S1 122.6(4) . . ?
C4 C3 S3 123.4(4) . . ?
S1 C3 S3 114.0(3) . . ?
C3 C4 S2 123.3(4) . . ?
C3 C4 S4 123.0(4) . . ?
S2 C4 S4 113.6(3) . . ?
C6 C5 C9 125.2(4) . . ?
C6 C5 S2 117.0(4) . . ?
C9 C5 S2 117.7(4) . . ?
C5 C6 C11 125.0(4) . . ?
C5 C6 S4 117.3(4) . . ?
C11 C6 S4 117.7(4) . . ?
C10 C9 C5 175.1(6) . . ?
C9 C10 Si1 174.3(6) . . ?
C12 C11 C6 178.9(6) . . ?
C11 C12 Si2 178.5(5) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        22.99
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 982421'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_8
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 N6 S4'
_chemical_formula_sum            'C26 H22 N6 S4'
_chemical_formula_weight         546.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   6.7025(5)
_cell_length_b                   19.621(2)
_cell_length_c                   20.267(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2665.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4058
_cell_measurement_theta_min      3.71
_cell_measurement_theta_max      24.03

_exptl_crystal_description       orange
_exptl_crystal_colour            plate
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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_type  area_detector
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13973
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.71
_diffrn_reflns_theta_max         24.03
_reflns_number_total             4058
_reflns_number_gt                2912
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       KappaCCD
_computing_cell_refinement       'Dirax/1sq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0195P)²+1.3413P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   0.02(11)
_refine_ls_number_reflns         4058
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.3361(2) 0.20518(6) 0.65313(7) 0.0626(4) Uani 1 1 d . . .
S2 S -0.4054(2) 0.34635(6) 0.60975(7) 0.0676(4) Uani 1 1 d . . .
S3 S 0.03890(17) 0.25106(5) 0.73896(6) 0.0530(3) Uani 1 1 d . . .
S4 S -0.00930(19) 0.39389(5) 0.69470(6) 0.0578(3) Uani 1 1 d . . .
N1 N 0.2644(5) 0.28612(17) 0.89445(17) 0.0441(9) Uani 1 1 d . . .
N2 N 0.4147(6) 0.2624(2) 0.9314(2) 0.0634(11) Uani 1 1 d . . .
N3 N 0.5639(6) 0.2491(2) 0.8924(2) 0.0703(12) Uani 1 1 d . . .
N4 N 0.2208(5) 0.49799(17) 0.80000(19) 0.0479(9) Uani 1 1 d . . .
N5 N 0.3719(7) 0.53499(19) 0.8252(2) 0.0654(12) Uani 1 1 d . . .
N6 N 0.5318(6) 0.4969(2) 0.8242(2) 0.0719(13) Uani 1 1 d . . .
C1 C -0.5522(7) 0.2209(2) 0.6064(2) 0.0577(13) Uani 1 1 d . . .
C2 C -0.5821(7) 0.2844(3) 0.5868(2) 0.0586(13) Uani 1 1 d . . .
C3 C -0.2595(7) 0.2907(2) 0.6568(2) 0.0497(11) Uani 1 1 d . . .
C4 C -0.1011(6) 0.3099(2) 0.6921(2) 0.0468(11) Uani 1 1 d . . .
C5 C 0.1830(6) 0.3132(2) 0.7782(2) 0.0404(11) Uani 1 1 d . . .
C6 C 0.1628(6) 0.3784(2) 0.7586(2) 0.0405(10) Uani 1 1 d . . .
C7 C 0.3166(6) 0.2887(2) 0.8305(2) 0.0390(10) Uani 1 1 d . . .
C8 C 0.5073(7) 0.2640(2) 0.8303(3) 0.0578(12) Uani 1 1 d . . .
H8 H 0.5861 0.2583 0.7929 0.069 Uiso 1 1 calc R . .
C9 C 0.2850(6) 0.4344(2) 0.7837(2) 0.0435(11) Uani 1 1 d . . .
C10 C 0.4838(7) 0.4356(2) 0.7997(2) 0.0604(13) Uani 1 1 d . . .
H10 H 0.5719 0.3994 0.7943 0.073 Uiso 1 1 calc R . .
C11 C -0.6795(8) 0.1594(3) 0.5914(3) 0.0876(18) Uani 1 1 d . . .
H11A H -0.6241 0.1201 0.6128 0.131 Uiso 1 1 calc R . .
H11B H -0.6827 0.1520 0.5446 0.131 Uiso 1 1 calc R . .
H11C H -0.8126 0.1670 0.6073 0.131 Uiso 1 1 calc R . .
C12 C -0.7522(7) 0.3096(3) 0.5439(3) 0.0811(17) Uani 1 1 d . . .
H12A H -0.7381 0.3577 0.5366 0.122 Uiso 1 1 calc R . .
H12B H -0.8769 0.3007 0.5656 0.122 Uiso 1 1 calc R . .
H12C H -0.7494 0.2862 0.5023 0.122 Uiso 1 1 calc R . .
C13 C 0.0737(7) 0.3038(2) 0.9253(2) 0.0556(12) Uani 1 1 d . . .
H13A H 0.0593 0.2778 0.9658 0.067 Uiso 1 1 calc R . .
H13B H -0.0338 0.2907 0.8960 0.067 Uiso 1 1 calc R . .
C14 C 0.0538(7) 0.3785(2) 0.9411(2) 0.0488(12) Uani 1 1 d . . .
C15 C 0.2132(8) 0.4191(3) 0.9569(3) 0.0744(16) Uani 1 1 d . . .
H15 H 0.3414 0.4011 0.9556 0.089 Uiso 1 1 calc R . .
C16 C 0.1860(10) 0.4864(3) 0.9748(3) 0.0880(19) Uani 1 1 d . . .
H16 H 0.2956 0.5132 0.9856 0.106 Uiso 1 1 calc R . .
C17 C 0.0000(12) 0.5134(3) 0.9767(3) 0.0845(17) Uani 1 1 d . . .
H17 H -0.0192 0.5584 0.9899 0.101 Uiso 1 1 calc R . .
C18 C -0.1581(10) 0.4741(4) 0.9592(3) 0.095(2) Uani 1 1 d . . .
H18 H -0.2854 0.4929 0.9593 0.114 Uiso 1 1 calc R . .
C19 C -0.1343(8) 0.4071(3) 0.9414(3) 0.0762(16) Uani 1 1 d . . .
H19 H -0.2446 0.3811 0.9295 0.091 Uiso 1 1 calc R . .
C20 C 0.0287(7) 0.5307(2) 0.7923(2) 0.0572(13) Uani 1 1 d . . .
H20A H 0.0152 0.5661 0.8254 0.069 Uiso 1 1 calc R . .
H20B H -0.0757 0.4974 0.7999 0.069 Uiso 1 1 calc R . .
C21 C 0.0001(8) 0.56198(19) 0.7248(2) 0.0527(12) Uani 1 1 d . . .
C22 C 0.1580(8) 0.5832(3) 0.6863(3) 0.0710(15) Uani 1 1 d . . .
H22 H 0.2878 0.5775 0.7015 0.085 Uiso 1 1 calc R . .
C23 C 0.1254(11) 0.6127(3) 0.6260(3) 0.092(2) Uani 1 1 d . . .
H23 H 0.2333 0.6274 0.6009 0.111 Uiso 1 1 calc R . .
C24 C -0.0630(12) 0.6207(3) 0.6027(3) 0.0864(18) Uani 1 1 d . . .
H24 H -0.0837 0.6400 0.5613 0.104 Uiso 1 1 calc R . .
C25 C -0.2199(10) 0.6008(3) 0.6393(4) 0.099(2) Uani 1 1 d . . .
H25 H -0.3490 0.6066 0.6234 0.119 Uiso 1 1 calc R . .
C26 C -0.1891(9) 0.5716(3) 0.7009(3) 0.0843(18) Uani 1 1 d . . .
H26 H -0.2981 0.5583 0.7263 0.101 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 C3 1.756(4) . ?
S1 C1 1.758(5) . ?
S2 C3 1.749(4) . ?
S2 C2 1.760(5) . ?
S3 C5 1.747(4) . ?
S3 C4 1.764(4) . ?
S4 C4 1.760(4) . ?
S4 C6 1.761(4) . ?
N1 N2 1.339(5) . ?
N1 C7 1.343(5) . ?
N1 C13 1.465(5) . ?
N2 N3 1.301(5) . ?
N3 C8 1.348(6) . ?
N4 N5 1.346(5) . ?
N4 C9 1.360(5) . ?
N4 C20 1.447(5) . ?
N5 N6 1.307(5) . ?
N6 C10 1.340(5) . ?
C1 C2 1.322(6) . ?
C1 C11 1.509(6) . ?
C2 C12 1.517(6) . ?
C3 C4 1.334(5) . ?
C5 C6 1.347(5) . ?
C5 C7 1.468(5) . ?
C6 C9 1.461(5) . ?
C7 C8 1.367(6) . ?
C9 C10 1.372(6) . ?
C13 C14 1.506(6) . ?
C14 C15 1.370(6) . ?
C14 C19 1.380(6) . ?
C15 C16 1.381(7) . ?
C16 C17 1.355(8) . ?
C17 C18 1.359(8) . ?
C18 C19 1.372(7) . ?
C20 C21 1.512(6) . ?
C21 C26 1.370(7) . ?
C21 C22 1.378(7) . ?
C22 C23 1.370(7) . ?
C23 C24 1.358(8) . ?
C24 C25 1.346(8) . ?
C25 C26 1.390(8) . ?

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
C3 S1 C1 95.5(2) . . ?
C3 S2 C2 95.1(2) . . ?
C5 S3 C4 94.8(2) . . ?
C4 S4 C6 95.1(2) . . ?
N2 N1 C7 110.9(3) . . ?
N2 N1 C13 120.0(4) . . ?
C7 N1 C13 129.1(4) . . ?
N3 N2 N1 107.9(4) . . ?
N2 N3 C8 108.0(4) . . ?
N5 N4 C9 110.4(3) . . ?
N5 N4 C20 118.1(3) . . ?
C9 N4 C20 131.5(4) . . ?
N6 N5 N4 107.6(3) . . ?
N5 N6 C10 108.8(4) . . ?
C2 C1 C11 127.4(5) . . ?
C2 C1 S1 116.9(4) . . ?
C11 C1 S1 115.7(4) . . ?
C1 C2 C12 126.4(5) . . ?
C1 C2 S2 118.0(4) . . ?
C12 C2 S2 115.7(4) . . ?
C4 C3 S2 124.1(3) . . ?
C4 C3 S1 121.7(3) . . ?
S2 C3 S1 114.2(2) . . ?
C3 C4 S4 123.9(3) . . ?
C3 C4 S3 121.8(3) . . ?
S4 C4 S3 114.3(2) . . ?
C6 C5 C7 125.8(4) . . ?
C6 C5 S3 118.2(3) . . ?
C7 C5 S3 116.0(3) . . ?
C5 C6 C9 123.8(4) . . ?
C5 C6 S4 116.5(3) . . ?
C9 C6 S4 119.5(3) . . ?
N1 C7 C8 103.5(4) . . ?
N1 C7 C5 123.3(4) . . ?
C8 C7 C5 133.1(4) . . ?
N3 C8 C7 109.6(4) . . ?
N4 C9 C10 103.5(4) . . ?
N4 C9 C6 126.6(4) . . ?
C10 C9 C6 129.7(4) . . ?
N6 C10 C9 109.7(4) . . ?
N1 C13 C14 113.5(4) . . ?
C15 C14 C19 118.4(4) . . ?
C15 C14 C13 123.1(4) . . ?
C19 C14 C13 118.5(4) . . ?
C14 C15 C16 120.9(5) . . ?
C17 C16 C15 120.2(5) . . ?
C16 C17 C18 119.2(5) . . ?
C17 C18 C19 121.5(6) . . ?
C18 C19 C14 119.8(5) . . ?
N4 C20 C21 113.0(4) . . ?
C26 C21 C22 118.0(5) . . ?
C26 C21 C20 119.5(5) . . ?
C22 C21 C20 122.5(5) . . ?
C23 C22 C21 120.7(6) . . ?
C24 C23 C22 120.5(6) . . ?
C25 C24 C23 120.1(6) . . ?
C24 C25 C26 120.0(6) . . ?
C21 C26 C25 120.7(6) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        24.03
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 982422'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_9
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 B F4 N3 S4'
_chemical_formula_sum            'C18 H18 B F4 N3 S4'
_chemical_formula_weight         491.40

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'
F F 0.0171 0.0103 '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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7854(6)
_cell_length_b                   11.1730(7)
_cell_length_c                   11.3320(5)
_cell_angle_alpha                70.909(4)
_cell_angle_beta                 81.108(4)
_cell_angle_gamma                68.833(4)
_cell_volume                     1090.88(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4719
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.00

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6676
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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_type  area_detector
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21173
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4719
_reflns_number_gt                3837
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       KappaCCD
_computing_cell_refinement       'Dirax/1sq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1343P)²+0.8764P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4719
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.2255
_refine_ls_wR_factor_gt          0.2094
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.003
_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 0.59845(10) -0.22956(9) 0.65232(8) 0.0496(3) Uani 1 1 d . . .
S2 S 0.76554(9) -0.05834(9) 0.49677(8) 0.0483(3) Uani 1 1 d . . .
S3 S 0.43897(9) -0.01796(8) 0.80730(7) 0.0433(3) Uani 1 1 d . . .
S4 S 0.61417(10) 0.15379(9) 0.66242(8) 0.0498(3) Uani 1 1 d . . .
B1 B 0.7880(4) 0.2936(4) 0.8971(4) 0.0528(9) Uani 1 1 d . . .
F1 F 0.9012(6) 0.1765(5) 0.9071(6) 0.170(2) Uani 1 1 d . . .
F2 F 0.7515(6) 0.3045(7) 0.7830(5) 0.169(2) Uani 1 1 d . . .
F3 F 0.8551(7) 0.3705(7) 0.9095(7) 0.213(3) Uani 1 1 d . . .
F4 F 0.6969(5) 0.2517(6) 0.9915(5) 0.1487(19) Uani 1 1 d . . .
C1 C 0.7165(4) -0.2863(3) 0.5338(3) 0.0473(8) Uani 1 1 d . . .
C2 C 0.7934(4) -0.2095(3) 0.4634(3) 0.0467(7) Uani 1 1 d . . .
C3 C 0.6360(3) -0.0807(3) 0.6202(3) 0.0395(6) Uani 1 1 d . . .
C4 C 0.5710(3) 0.0080(3) 0.6859(3) 0.0389(6) Uani 1 1 d . . .
C6 C 0.4970(3) 0.2040(3) 0.7810(3) 0.0440(7) Uani 1 1 d . . .
H6 H 0.4904 0.2818 0.7982 0.053 Uiso 1 1 calc R . .
C5 C 0.4159(3) 0.1285(3) 0.8475(3) 0.0374(6) Uani 1 1 d . . .
C7 C 0.3081(3) 0.1498(3) 0.9496(3) 0.0366(6) Uani 1 1 d . . .
C8 C 0.2245(4) 0.0710(3) 1.0137(3) 0.0432(7) Uani 1 1 d . . .
H8 H 0.2245 -0.0070 1.0008 0.052 Uiso 1 1 calc R . .
C9 C 0.7201(6) -0.4186(4) 0.5240(5) 0.0705(11) Uani 1 1 d . . .
H9A H 0.6540 -0.4523 0.5865 0.106 Uiso 1 1 calc R . .
H9B H 0.8178 -0.4817 0.5366 0.106 Uiso 1 1 calc R . .
H9C H 0.6907 -0.4061 0.4426 0.106 Uiso 1 1 calc R . .
C10 C 0.9016(5) -0.2371(5) 0.3584(4) 0.0667(11) Uani 1 1 d . . .
H10A H 0.9402 -0.1646 0.3234 0.100 Uiso 1 1 calc R . .
H10B H 0.8537 -0.2453 0.2950 0.100 Uiso 1 1 calc R . .
H10C H 0.9803 -0.3193 0.3896 0.100 Uiso 1 1 calc R . .
C11 C 0.3180(4) 0.3672(3) 0.9765(3) 0.0449(7) Uani 1 1 d . . .
H11A H 0.4243 0.3380 0.9702 0.054 Uiso 1 1 calc R . .
H11B H 0.2858 0.4069 1.0447 0.054 Uiso 1 1 calc R . .
C12 C 0.2579(3) 0.4723(3) 0.8559(3) 0.0406(7) Uani 1 1 d . . .
C13 C 0.1193(4) 0.4944(4) 0.8188(4) 0.0486(8) Uani 1 1 d . . .
H13 H 0.0638 0.4417 0.8663 0.058 Uiso 1 1 calc R . .
C14 C 0.0651(4) 0.5944(4) 0.7116(4) 0.0606(10) Uani 1 1 d . . .
H14 H -0.0274 0.6090 0.6870 0.073 Uiso 1 1 calc R . .
C15 C 0.1466(5) 0.6739(4) 0.6393(4) 0.0624(10) Uani 1 1 d . . .
H15 H 0.1098 0.7406 0.5663 0.075 Uiso 1 1 calc R . .
C16 C 0.2813(5) 0.6530(4) 0.6768(4) 0.0654(10) Uani 1 1 d . . .
H16 H 0.3357 0.7068 0.6295 0.078 Uiso 1 1 calc R . .
C17 C 0.3383(4) 0.5523(4) 0.7848(4) 0.0563(9) Uani 1 1 d . . .
H17 H 0.4305 0.5389 0.8092 0.068 Uiso 1 1 calc R . .
C18 C 0.0314(5) 0.0887(5) 1.1891(4) 0.0628(10) Uani 1 1 d . . .
H18A H -0.0095 0.1498 1.2384 0.094 Uiso 1 1 calc R . .
H18B H 0.0760 -0.0002 1.2429 0.094 Uiso 1 1 calc R . .
H18C H -0.0451 0.0890 1.1450 0.094 Uiso 1 1 calc R . .
N3 N 0.1424(3) 0.1306(3) 1.0990(3) 0.0457(6) Uani 1 1 d . . .
N2 N 0.1681(3) 0.2386(3) 1.0955(3) 0.0468(6) Uani 1 1 d . . .
N1 N 0.2700(3) 0.2500(3) 1.0047(2) 0.0399(6) 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 C3 1.743(3) . ?
S1 C1 1.757(3) . ?
S2 C3 1.754(3) . ?
S2 C2 1.767(3) . ?
S3 C4 1.762(3) . ?
S3 C5 1.767(3) . ?
S4 C6 1.728(3) . ?
S4 C4 1.755(3) . ?
B1 F3 1.305(5) . ?
B1 F2 1.350(6) . ?
B1 F4 1.356(6) . ?
B1 F1 1.359(6) . ?
C1 C2 1.332(5) . ?
C1 C9 1.505(5) . ?
C2 C10 1.499(5) . ?
C3 C4 1.351(4) . ?
C6 C5 1.339(5) . ?
C5 C7 1.459(4) . ?
C7 N1 1.366(4) . ?
C7 C8 1.375(5) . ?
C8 N3 1.349(4) . ?
C11 N1 1.471(4) . ?
C11 C12 1.514(5) . ?
C12 C17 1.382(5) . ?
C12 C13 1.394(4) . ?
C13 C14 1.374(6) . ?
C14 C15 1.390(7) . ?
C15 C16 1.363(6) . ?
C16 C17 1.390(6) . ?
C18 N3 1.468(5) . ?
N3 N2 1.306(4) . ?
N2 N1 1.326(4) . ?

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
C3 S1 C1 96.16(16) . . ?
C3 S2 C2 95.81(16) . . ?
C4 S3 C5 94.73(14) . . ?
C6 S4 C4 95.35(15) . . ?
F3 B1 F2 120.4(5) . . ?
F3 B1 F4 119.0(5) . . ?
F2 B1 F4 113.9(4) . . ?
F3 B1 F1 101.1(5) . . ?
F2 B1 F1 94.8(5) . . ?
F4 B1 F1 100.2(5) . . ?
C2 C1 C9 127.0(3) . . ?
C2 C1 S1 117.3(3) . . ?
C9 C1 S1 115.7(3) . . ?
C1 C2 C10 127.1(3) . . ?
C1 C2 S2 116.8(2) . . ?
C10 C2 S2 116.2(3) . . ?
C4 C3 S1 122.3(3) . . ?
C4 C3 S2 123.7(3) . . ?
S1 C3 S2 113.99(16) . . ?
C3 C4 S4 123.5(3) . . ?
C3 C4 S3 121.8(3) . . ?
S4 C4 S3 114.64(16) . . ?
C5 C6 S4 118.6(2) . . ?
C6 C5 C7 129.2(3) . . ?
C6 C5 S3 116.7(2) . . ?
C7 C5 S3 114.1(2) . . ?
N1 C7 C8 104.6(3) . . ?
N1 C7 C5 128.1(3) . . ?
C8 C7 C5 127.3(3) . . ?
N3 C8 C7 105.6(3) . . ?
N1 C11 C12 112.2(2) . . ?
C17 C12 C13 119.4(3) . . ?
C17 C12 C11 119.5(3) . . ?
C13 C12 C11 121.1(3) . . ?
C14 C13 C12 119.7(4) . . ?
C13 C14 C15 120.9(4) . . ?
C16 C15 C14 119.1(4) . . ?
C15 C16 C17 120.9(4) . . ?
C12 C17 C16 120.0(3) . . ?
N2 N3 C8 113.0(3) . . ?
N2 N3 C18 119.3(3) . . ?
C8 N3 C18 127.6(3) . . ?
N3 N2 N1 104.6(2) . . ?
N2 N1 C7 112.1(3) . . ?
N2 N1 C11 116.8(2) . . ?
C7 N1 C11 131.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.328
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.087
_database_code_depnum_ccdc_archive 'CCDC 982423'
