 
data_01sot025
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C52 H44 N4 O6 S2' 
_chemical_formula_weight          885.03 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'S'  'S'   0.1246   0.1234 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/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                    16.4380(3) 
_cell_length_b                    7.82380(10) 
_cell_length_c                    18.1280(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  109.970(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      2191.22(6) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     6766 
_cell_measurement_theta_min       1.00 
_cell_measurement_theta_max       26.02 
 
_exptl_crystal_description        'hexagonal prism' 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.15 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.08 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.341 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              928 
_exptl_absorpt_coefficient_mu     0.179 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9736 
_exptl_absorpt_correction_T_max   0.9858 
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD' 
_diffrn_measurement_method        'Φ & ω scans' 
_diffrn_detector_area_resol_mean  9.091 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             12475 
_diffrn_reflns_av_R_equivalents   0.1479 
_diffrn_reflns_av_sigmaI/netI     0.1541 
_diffrn_reflns_limit_h_min        -19 
_diffrn_reflns_limit_h_max        19 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -20 
_diffrn_reflns_limit_l_max        21 
_diffrn_reflns_theta_min          2.92 
_diffrn_reflns_theta_max          25.02 
_reflns_number_total              3848 
_reflns_number_gt                 1938 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'COLLECT (Hooft, 1998)' 
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'  
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'  
_computing_structure_solution     'SHELXS-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)+(0.0413P)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      SHELXL 
_refine_ls_extinction_coef        0.0032(8) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3848 
_refine_ls_number_parameters      290 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1481 
_refine_ls_R_factor_gt            0.0580 
_refine_ls_wR_factor_ref          0.1363 
_refine_ls_wR_factor_gt           0.1088 
_refine_ls_goodness_of_fit_ref    0.947 
_refine_ls_restrained_S_all       0.947 
_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 
C1 C 0.0474(2) 1.0144(5) -0.0879(2) 0.0357(10) Uani 1 1 d . . . 
H1 H 0.0297 1.0124 -0.0432 0.043 Uiso 1 1 calc R . . 
C2 C 0.0374(3) 1.1618(5) -0.1313(2) 0.0395(11) Uani 1 1 d . . . 
H2 H 0.0122 1.2598 -0.1168 0.047 Uiso 1 1 calc R . . 
C3 C 0.0636(2) 1.1684(5) -0.1958(2) 0.0357(10) Uani 1 1 d . . . 
H3 H 0.0572 1.2705 -0.2255 0.043 Uiso 1 1 calc R . . 
C4 C 0.0989(2) 1.0262(5) -0.2162(2) 0.0375(10) Uani 1 1 d . . . 
H4 H 0.1164 1.0290 -0.2610 0.045 Uiso 1 1 calc R . . 
C5 C 0.1096(2) 0.8775(5) -0.1724(2) 0.0347(10) Uani 1 1 d . . . 
H5 H 0.1357 0.7803 -0.1866 0.042 Uiso 1 1 calc R . . 
C6 C 0.0824(2) 0.8697(4) -0.10796(19) 0.0241(9) Uani 1 1 d . . . 
C7 C 0.0992(2) 0.7134(4) -0.0591(2) 0.0261(9) Uani 1 1 d . . . 
C8 C 0.1815(2) 0.6296(5) -0.0263(2) 0.0262(9) Uani 1 1 d . . . 
C9 C 0.2641(2) 0.6900(5) -0.0340(2) 0.0292(9) Uani 1 1 d . . . 
C10 C 0.2876(2) 0.8605(5) -0.0224(2) 0.0315(9) Uani 1 1 d . . . 
H10 H 0.2507 0.9388 -0.0089 0.038 Uiso 1 1 calc R . . 
C11 C 0.3638(3) 0.9188(5) -0.0300(2) 0.0408(11) Uani 1 1 d . . . 
H11 H 0.3792 1.0360 -0.0215 0.049 Uiso 1 1 calc R . . 
C12 C 0.4173(3) 0.8052(6) -0.0499(2) 0.0432(11) Uani 1 1 d . . . 
H12 H 0.4695 0.8448 -0.0555 0.052 Uiso 1 1 calc R . . 
C13 C 0.3955(3) 0.6366(6) -0.0616(2) 0.0433(11) Uani 1 1 d . . . 
H13 H 0.4326 0.5595 -0.0754 0.052 Uiso 1 1 calc R . . 
C14 C 0.3192(2) 0.5771(5) -0.0535(2) 0.0355(10) Uani 1 1 d . . . 
H14 H 0.3047 0.4593 -0.0611 0.043 Uiso 1 1 calc R . . 
C15 C 0.1724(2) 0.4932(4) 0.0168(2) 0.0260(9) Uani 1 1 d . . . 
C16 C 0.2427(2) 0.3756(5) 0.0659(2) 0.0273(9) Uani 1 1 d . . . 
C17 C 0.3501(2) 0.3543(4) 0.1993(2) 0.0270(9) Uani 1 1 d . . . 
C18 C 0.3535(2) 0.3623(5) 0.2767(2) 0.0345(10) Uani 1 1 d . . . 
H18 H 0.3086 0.4180 0.2894 0.041 Uiso 1 1 calc R . . 
C19 C 0.4224(3) 0.2892(5) 0.3358(2) 0.0412(11) Uani 1 1 d . . . 
H19 H 0.4247 0.2956 0.3888 0.049 Uiso 1 1 calc R . . 
C20 C 0.4876(3) 0.2074(5) 0.3179(2) 0.0444(11) Uani 1 1 d . . . 
H20 H 0.5342 0.1559 0.3582 0.053 Uiso 1 1 calc R . . 
C21 C 0.4846(3) 0.2008(5) 0.2410(3) 0.0407(11) Uani 1 1 d . . . 
H21 H 0.5298 0.1451 0.2287 0.049 Uiso 1 1 calc R . . 
C22 C 0.4168(2) 0.2741(5) 0.1815(2) 0.0341(10) Uani 1 1 d . . . 
H22 H 0.4157 0.2697 0.1288 0.041 Uiso 1 1 calc R . . 
C23 C 0.0419(2) 0.6198(4) -0.0338(2) 0.0245(8) Uani 1 1 d . . . 
C24 C 0.0513(2) 0.3636(5) 0.0511(2) 0.0267(9) Uani 1 1 d . . . 
C25 C 0.1821(3) 0.0021(5) 0.2281(2) 0.0443(11) Uani 1 1 d . . . 
H25A H 0.1213 0.0064 0.2246 0.066 Uiso 1 1 calc R . . 
H25B H 0.2020 0.1177 0.2223 0.066 Uiso 1 1 calc R . . 
H25C H 0.2173 -0.0445 0.2792 0.066 Uiso 1 1 calc R . . 
C26 C 0.3052(3) -0.1090(6) 0.1749(3) 0.0608(14) Uani 1 1 d . . . 
H26A H 0.3236 -0.1766 0.1379 0.091 Uiso 1 1 calc R . . 
H26B H 0.3352 -0.1498 0.2285 0.091 Uiso 1 1 calc R . . 
H26C H 0.3193 0.0116 0.1710 0.091 Uiso 1 1 calc R . . 
N1 N 0.08678(18) 0.4845(4) 0.01327(15) 0.0261(7) Uani 1 1 d . . . 
N2 N 0.27893(18) 0.4315(4) 0.14085(16) 0.0280(8) Uani 1 1 d . . . 
H2A H 0.2564 0.5233 0.1543 0.034 Uiso 1 1 calc R . . 
O1 O 0.26676(17) 0.2535(3) 0.03694(15) 0.0396(7) Uani 1 1 d . . . 
O2 O 0.09690(15) 0.2546(3) 0.09309(15) 0.0353(7) Uani 1 1 d . . . 
O3 O 0.17930(17) -0.3104(3) 0.17452(17) 0.0441(8) Uani 1 1 d . . . 
S1 S 0.19217(7) -0.13097(13) 0.15206(6) 0.0384(3) 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 
C1 C6 1.374(5) . ? 
C1 C2 1.374(5) . ? 
C2 C3 1.379(5) . ? 
C3 C4 1.363(5) . ? 
C4 C5 1.386(5) . ? 
C5 C6 1.387(5) . ? 
C6 C7 1.479(5) . ? 
C7 C23 1.389(5) . ? 
C7 C8 1.438(5) . ? 
C8 C15 1.360(5) . ? 
C8 C9 1.488(5) . ? 
C9 C10 1.385(5) . ? 
C9 C14 1.394(5) . ? 
C10 C11 1.383(5) . ? 
C11 C12 1.383(5) . ? 
C12 C13 1.364(5) . ? 
C13 C14 1.392(5) . ? 
C15 N1 1.389(4) . ? 
C15 C16 1.508(5) . ? 
C16 O1 1.219(4) . ? 
C16 N2 1.356(4) . ? 
C17 C18 1.387(5) . ? 
C17 C22 1.394(5) . ? 
C17 N2 1.418(4) . ? 
C18 C19 1.389(5) . ? 
C19 C20 1.378(5) . ? 
C20 C21 1.379(5) . ? 
C21 C22 1.384(5) . ? 
C23 N1 1.401(4) . ? 
C23 C24 1.461(5) 3_565 ? 
C24 O2 1.216(4) . ? 
C24 N1 1.407(4) . ? 
C24 C23 1.461(5) 3_565 ? 
C25 S1 1.780(4) . ? 
C26 S1 1.768(4) . ? 
O3 S1 1.497(3) . ? 
 
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 
C6 C1 C2 121.3(4) . . ? 
C1 C2 C3 120.4(4) . . ? 
C4 C3 C2 119.1(4) . . ? 
C3 C4 C5 120.8(4) . . ? 
C4 C5 C6 120.4(4) . . ? 
C1 C6 C5 118.1(3) . . ? 
C1 C6 C7 122.1(3) . . ? 
C5 C6 C7 119.5(3) . . ? 
C23 C7 C8 105.7(3) . . ? 
C23 C7 C6 128.7(3) . . ? 
C8 C7 C6 125.5(3) . . ? 
C15 C8 C7 108.8(3) . . ? 
C15 C8 C9 125.8(3) . . ? 
C7 C8 C9 125.2(3) . . ? 
C10 C9 C14 118.5(3) . . ? 
C10 C9 C8 120.5(3) . . ? 
C14 C9 C8 121.0(3) . . ? 
C11 C10 C9 121.1(4) . . ? 
C10 C11 C12 119.5(4) . . ? 
C13 C12 C11 120.4(4) . . ? 
C12 C13 C14 120.3(4) . . ? 
C13 C14 C9 120.1(4) . . ? 
C8 C15 N1 108.7(3) . . ? 
C8 C15 C16 127.3(3) . . ? 
N1 C15 C16 123.8(3) . . ? 
O1 C16 N2 126.0(3) . . ? 
O1 C16 C15 121.3(3) . . ? 
N2 C16 C15 112.4(3) . . ? 
C18 C17 C22 119.5(3) . . ? 
C18 C17 N2 118.3(3) . . ? 
C22 C17 N2 122.2(3) . . ? 
C17 C18 C19 120.2(4) . . ? 
C20 C19 C18 120.2(4) . . ? 
C19 C20 C21 119.6(4) . . ? 
C20 C21 C22 120.9(4) . . ? 
C21 C22 C17 119.6(4) . . ? 
C7 C23 N1 109.0(3) . . ? 
C7 C23 C24 131.4(3) . 3_565 ? 
N1 C23 C24 119.6(3) . 3_565 ? 
O2 C24 N1 120.4(3) . . ? 
O2 C24 C23 125.1(3) . 3_565 ? 
N1 C24 C23 114.5(3) . 3_565 ? 
C15 N1 C23 107.8(3) . . ? 
C15 N1 C24 126.4(3) . . ? 
C23 N1 C24 125.8(3) . . ? 
C16 N2 C17 125.4(3) . . ? 
O3 S1 C26 105.21(19) . . ? 
O3 S1 C25 106.20(17) . . ? 
C26 S1 C25 97.5(2) . . ? 
 
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 H2A O3  0.88 1.94 2.795(4) 164.9 1_565 
N2 H2A S1  0.88 2.90 3.741(3) 160.6 1_565 
 
_diffrn_measured_fraction_theta_max    0.994 
_diffrn_reflns_theta_full              25.02 
_diffrn_measured_fraction_theta_full   0.994 
_refine_diff_density_max    0.315 
_refine_diff_density_min   -0.313 
_refine_diff_density_rms    0.079 
