 
data_shelx
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C6 H6 N6 O6 S6' 
_chemical_formula_weight          450.53

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    8.616(6)
_cell_length_b                    9.784(7)
_cell_length_c                    10.822(7)
_cell_angle_alpha                 84.06(2)
_cell_angle_beta                  86.84(2)
_cell_angle_gamma                 86.69(2)
_cell_volume                      904.8(11)
_cell_formula_units_Z             2
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.654          
_exptl_crystal_F_000              456
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           ?
_exptl_crystal_size_min           ?
_exptl_absorpt_coefficient_mu     0.791
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   ?
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             10014
_diffrn_reflns_av_unetI/netI      0.2786
_diffrn_reflns_av_R_equivalents   0.2226
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          2.096
_diffrn_reflns_theta_max          30.543
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.803
_diffrn_measured_fraction_theta_full  0.936
_diffrn_reflns_Laue_measured_fraction_max    0.803
_diffrn_reflns_Laue_measured_fraction_full   0.936
_diffrn_reflns_point_group_measured_fraction_max   0.803
_diffrn_reflns_point_group_measured_fraction_full  0.936
_reflns_number_total              4453
_reflns_number_gt                 1344
_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        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4453
_refine_ls_number_parameters      235
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.3391
_refine_ls_R_factor_gt            0.2206
_refine_ls_wR_factor_ref          0.5284
_refine_ls_wR_factor_gt           0.4689
_refine_ls_goodness_of_fit_ref    1.190
_refine_ls_restrained_S_all       1.190
_refine_ls_shift/su_max           0.010
_refine_ls_shift/su_mean          0.002
 
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 -0.1672(3) 0.2974(3) 0.8339(3) 0.0574(10) Uani 1 1 d . . . . .
O2 O -0.2934(7) 0.3882(7) 0.7949(8) 0.068(2) Uani 1 1 d . . . . .
N1 N -0.1298(8) 0.1877(7) 0.7291(8) 0.051(2) Uani 1 1 d . . . . .
O4 O -0.1744(9) 0.2166(7) 0.9529(7) 0.067(2) Uani 1 1 d . . . . .
C17 C 0.2934(10) 0.1996(9) 0.4426(10) 0.052(3) Uani 1 1 d . . . . .
C1 C -0.0030(10) 0.3994(9) 0.8381(9) 0.051(3) Uani 1 1 d . . . . .
O7 O 0.3826(8) -0.0019(8) 0.7320(7) 0.067(2) Uani 1 1 d . . . . .
C18 C 0.3151(10) 0.0916(10) 0.5372(11) 0.056(3) Uani 1 1 d . . . . .
C12 C -0.2028(11) 0.1378(10) 0.5317(10) 0.055(3) Uani 1 1 d . . . . .
C10 C -0.1590(12) -0.1225(10) 0.7509(11) 0.057(3) Uani 1 1 d . . . . .
C3 C 0.2360(12) 0.4425(10) 0.9210(11) 0.067(3) Uani 1 1 d . . . . .
H3 H 0.3117 0.4191 0.9786 0.080 Uiso 1 1 calc R U . . .
C8 C -0.0072(11) 0.0800(11) 0.7593(11) 0.071(4) Uani 1 1 d . . . . .
H8A H 0.0665 0.1163 0.8105 0.085 Uiso 1 1 calc R U . . .
H8B H 0.0484 0.0587 0.6827 0.085 Uiso 1 1 calc R U . . .
C33 C 0.2267(12) 0.1703(9) 0.3284(12) 0.064(3) Uani 1 1 d . . . . .
C13 C 0.3760(11) 0.1108(11) 0.6483(12) 0.068(4) Uani 1 1 d . . . . .
C6 C 0.0143(12) 0.5099(9) 0.7503(11) 0.063(3) Uani 1 1 d . . . . .
H6 H -0.0605 0.5303 0.6915 0.076 Uiso 1 1 calc R U . . .
C2 C 0.1068(12) 0.3655(11) 0.9291(10) 0.063(3) Uani 1 1 d . . . . .
H2 H 0.0927 0.2944 0.9920 0.076 Uiso 1 1 calc R U . . .
C9 C -0.0657(11) -0.0529(10) 0.8272(11) 0.066(3) Uani 1 1 d . . . . .
H9A H 0.0227 -0.1132 0.8527 0.079 Uiso 1 1 calc R U . . .
H9B H -0.1266 -0.0320 0.9016 0.079 Uiso 1 1 calc R U . . .
C14 C 0.4208(14) 0.2394(12) 0.6686(12) 0.071(3) Uani 1 1 d . . . . .
H14 H 0.4634 0.2535 0.7431 0.085 Uiso 1 1 calc R U . . .
C4 C 0.2599(12) 0.5488(11) 0.8356(11) 0.065(3) Uani 1 1 d . . . . .
C11 C -0.1464(14) 0.2479(10) 0.5963(11) 0.067(3) Uani 1 1 d . . . . .
H11A H -0.2201 0.3268 0.5923 0.081 Uiso 1 1 calc R U . . .
H11B H -0.0469 0.2767 0.5593 0.081 Uiso 1 1 calc R U . . .
C5 C 0.1359(12) 0.5887(10) 0.7473(10) 0.064(3) Uani 1 1 d . . . . .
H5 H 0.1427 0.6670 0.6911 0.077 Uiso 1 1 calc R U . . .
C7 C 0.4011(14) 0.6353(12) 0.8385(15) 0.105(5) Uani 1 1 d . . . . .
H7A H 0.3994 0.7067 0.7706 0.157 Uiso 1 1 calc R U . . .
H7B H 0.3982 0.6758 0.9157 0.157 Uiso 1 1 calc R U . . .
H7C H 0.4946 0.5778 0.8309 0.157 Uiso 1 1 calc R U . . .
C23 C 0.4472(15) 0.0115(13) 0.8482(11) 0.080(4) Uani 1 1 d . . . . .
H23A H 0.4452 -0.0750 0.8989 0.120 Uiso 1 1 calc R U . . .
H23B H 0.5527 0.0381 0.8343 0.120 Uiso 1 1 calc R U . . .
H23C H 0.3871 0.0804 0.8898 0.120 Uiso 1 1 calc R U . . .
C16 C 0.3409(12) 0.3270(11) 0.4634(11) 0.064(3) Uani 1 1 d . . . . .
H16 H 0.3323 0.3997 0.4013 0.077 Uiso 1 1 calc R U . . .
C15 C 0.4012(13) 0.3483(11) 0.5755(11) 0.065(3) Uani 1 1 d . . . . .
H15 H 0.4289 0.4359 0.5889 0.079 Uiso 1 1 calc R U . . .
C34 C 0.2607(11) -0.0432(11) 0.5087(12) 0.071(4) 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 O2 1.418(6) . ?
S1 O4 1.440(7) . ?
S1 N1 1.648(9) . ?
S1 C1 1.783(10) . ?
N1 C8 1.473(10) . ?
N1 C11 1.506(13) . ?
C17 C16 1.378(15) . ?
C17 C18 1.405(12) . ?
C17 C33 1.453(17) . ?
C1 C6 1.373(11) . ?
C1 C2 1.405(12) . ?
O7 C13 1.353(11) . ?
O7 C23 1.424(13) . ?
C18 C13 1.372(16) . ?
C18 C34 1.492(16) . ?
C12 C34 1.208(16) 2_556 ?
C12 C11 1.463(15) . ?
C10 C33 1.210(15) 2_556 ?
C10 C9 1.431(16) . ?
C3 C4 1.335(13) . ?
C3 C2 1.374(14) . ?
C3 H3 0.9300 . ?
C8 C9 1.523(13) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C33 C10 1.210(15) 2_556 ?
C13 C14 1.380(16) . ?
C6 C5 1.333(13) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C14 C15 1.398(14) . ?
C14 H14 0.9300 . ?
C4 C5 1.481(14) . ?
C4 C7 1.525(15) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C5 H5 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C16 C15 1.385(16) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C34 C12 1.208(16) 2_556 ?
 
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
O2 S1 O4 121.1(5) . . ?
O2 S1 N1 108.4(4) . . ?
O4 S1 N1 106.3(4) . . ?
O2 S1 C1 106.9(4) . . ?
O4 S1 C1 104.8(5) . . ?
N1 S1 C1 108.8(5) . . ?
C8 N1 C11 120.0(9) . . ?
C8 N1 S1 115.4(7) . . ?
C11 N1 S1 114.9(6) . . ?
C16 C17 C18 117.3(11) . . ?
C16 C17 C33 124.0(9) . . ?
C18 C17 C33 118.7(9) . . ?
C6 C1 C2 121.1(10) . . ?
C6 C1 S1 118.7(7) . . ?
C2 C1 S1 120.2(7) . . ?
C13 O7 C23 117.6(10) . . ?
C13 C18 C17 122.4(10) . . ?
C13 C18 C34 123.1(9) . . ?
C17 C18 C34 114.5(10) . . ?
C34 C12 C11 172.1(12) 2_556 . ?
C33 C10 C9 170.2(10) 2_556 . ?
C4 C3 C2 124.2(10) . . ?
C4 C3 H3 117.9 . . ?
C2 C3 H3 117.9 . . ?
N1 C8 C9 114.8(8) . . ?
N1 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
N1 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C10 C33 C17 166.1(9) 2_556 . ?
O7 C13 C18 115.2(10) . . ?
O7 C13 C14 125.1(12) . . ?
C18 C13 C14 119.7(10) . . ?
C5 C6 C1 121.6(10) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C3 C2 C1 116.9(9) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C10 C9 C8 111.9(8) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C13 C14 C15 119.0(11) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C3 C4 C5 117.5(10) . . ?
C3 C4 C7 120.9(11) . . ?
C5 C4 C7 121.3(9) . . ?
C12 C11 N1 105.6(7) . . ?
C12 C11 H11A 110.6 . . ?
N1 C11 H11A 110.6 . . ?
C12 C11 H11B 110.6 . . ?
N1 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
C6 C5 C4 118.5(9) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O7 C23 H23A 109.5 . . ?
O7 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O7 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C17 C16 C15 121.0(10) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C15 C14 120.6(11) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C12 C34 C18 167.9(10) 2_556 . ?
 
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
O2 S1 N1 C8 -176.4(6) . . . . ?
O4 S1 N1 C8 -44.7(7) . . . . ?
C1 S1 N1 C8 67.7(7) . . . . ?
O2 S1 N1 C11 37.6(7) . . . . ?
O4 S1 N1 C11 169.3(6) . . . . ?
C1 S1 N1 C11 -78.4(7) . . . . ?
O2 S1 C1 C6 -35.4(11) . . . . ?
O4 S1 C1 C6 -165.2(8) . . . . ?
N1 S1 C1 C6 81.5(9) . . . . ?
O2 S1 C1 C2 145.2(10) . . . . ?
O4 S1 C1 C2 15.5(11) . . . . ?
N1 S1 C1 C2 -97.9(10) . . . . ?
C16 C17 C18 C13 2.2(15) . . . . ?
C33 C17 C18 C13 -179.4(9) . . . . ?
C16 C17 C18 C34 179.8(9) . . . . ?
C33 C17 C18 C34 -1.8(13) . . . . ?
C11 N1 C8 C9 -123.8(10) . . . . ?
S1 N1 C8 C9 92.0(10) . . . . ?
C16 C17 C33 C10 -159(4) . . . 2_556 ?
C18 C17 C33 C10 22(5) . . . 2_556 ?
C23 O7 C13 C18 179.0(10) . . . . ?
C23 O7 C13 C14 -2.9(15) . . . . ?
C17 C18 C13 O7 177.0(8) . . . . ?
C34 C18 C13 O7 -0.5(15) . . . . ?
C17 C18 C13 C14 -1.2(16) . . . . ?
C34 C18 C13 C14 -178.7(10) . . . . ?
C2 C1 C6 C5 0.4(19) . . . . ?
S1 C1 C6 C5 -178.9(9) . . . . ?
C4 C3 C2 C1 2(2) . . . . ?
C6 C1 C2 C3 -4.0(18) . . . . ?
S1 C1 C2 C3 175.3(9) . . . . ?
N1 C8 C9 C10 66.1(14) . . . . ?
O7 C13 C14 C15 -177.2(10) . . . . ?
C18 C13 C14 C15 0.8(17) . . . . ?
C2 C3 C4 C5 2.3(19) . . . . ?
C2 C3 C4 C7 175.7(12) . . . . ?
C8 N1 C11 C12 69.3(11) . . . . ?
S1 N1 C11 C12 -146.3(7) . . . . ?
C1 C6 C5 C4 4.5(18) . . . . ?
C3 C4 C5 C6 -5.9(17) . . . . ?
C7 C4 C5 C6 -179.2(12) . . . . ?
C18 C17 C16 C15 -2.8(15) . . . . ?
C33 C17 C16 C15 178.9(10) . . . . ?
C17 C16 C15 C14 2.4(17) . . . . ?
C13 C14 C15 C16 -1.4(17) . . . . ?
C13 C18 C34 C12 163(5) . . . 2_556 ?
C17 C18 C34 C12 -14(6) . . . 2_556 ?
 
_refine_diff_density_max    0.833
_refine_diff_density_min   -0.840
_refine_diff_density_rms    0.212



