 
data_01sot092
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C32 H29 N3 O3 S' 
_chemical_formula_weight          535.64 
 
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)/n 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
 
_cell_length_a                    9.6860(2) 
_cell_length_b                    18.6429(4) 
_cell_length_c                    15.5603(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  104.503(5) 
_cell_angle_gamma                 90.00 
_cell_volume                      2720.27(10) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used     12614 
_cell_measurement_theta_min       2.91 
_cell_measurement_theta_max       27.10 
 
_exptl_crystal_description        'cut needle' 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.10 
_exptl_crystal_size_mid           0.02 
_exptl_crystal_size_min           0.02 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.308 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1128 
_exptl_absorpt_coefficient_mu     0.158 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9844 
_exptl_absorpt_correction_T_max   0.9968 
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       120(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             19625 
_diffrn_reflns_av_R_equivalents   0.1853 
_diffrn_reflns_av_sigmaI/netI     0.1425 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -21 
_diffrn_reflns_limit_k_max        21 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          2.92 
_diffrn_reflns_theta_max          24.70 
_reflns_number_total              4605 
_reflns_number_gt                 2619 
_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)+(0.0529P)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        0.0042(7) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          4605 
_refine_ls_number_parameters      355 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1302 
_refine_ls_R_factor_gt            0.0616 
_refine_ls_wR_factor_ref          0.1500 
_refine_ls_wR_factor_gt           0.1249 
_refine_ls_goodness_of_fit_ref    0.995 
_refine_ls_restrained_S_all       0.995 
_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 
C1 C 0.3299(4) -0.11497(19) 0.3653(2) 0.0261(9) Uani 1 1 d . . . 
H1 H 0.3273 -0.1476 0.3180 0.031 Uiso 1 1 calc R . . 
C2 C 0.3646(4) -0.1387(2) 0.4529(2) 0.0296(10) Uani 1 1 d . . . 
H2 H 0.3869 -0.1879 0.4649 0.035 Uiso 1 1 calc R . . 
C3 C 0.3674(4) -0.09260(19) 0.5225(2) 0.0287(9) Uani 1 1 d . . . 
H3 H 0.3926 -0.1096 0.5819 0.034 Uiso 1 1 calc R . . 
C4 C 0.3334(4) -0.0216(2) 0.5048(2) 0.0302(10) Uani 1 1 d . . . 
H4 H 0.3336 0.0105 0.5523 0.036 Uiso 1 1 calc R . . 
C5 C 0.2989(4) 0.00361(18) 0.4187(2) 0.0236(9) Uani 1 1 d . . . 
H5 H 0.2749 0.0527 0.4074 0.028 Uiso 1 1 calc R . . 
C6 C 0.2989(4) -0.04261(18) 0.3480(2) 0.0204(9) Uani 1 1 d . . . 
C7 C 0.2628(4) -0.04269(19) 0.1831(2) 0.0212(8) Uani 1 1 d . . . 
C8 C 0.2651(4) 0.00525(17) 0.1073(2) 0.0186(8) Uani 1 1 d . . . 
C9 C 0.2446(4) -0.01158(18) 0.0181(2) 0.0199(8) Uani 1 1 d . . . 
C10 C 0.2727(4) 0.05144(18) -0.0255(2) 0.0203(8) Uani 1 1 d . . . 
C11 C 0.3106(4) 0.10449(18) 0.0392(2) 0.0196(8) Uani 1 1 d . . . 
C12 C 0.3486(4) 0.18159(18) 0.0391(2) 0.0222(9) Uani 1 1 d . . . 
C13 C 0.3842(4) 0.28144(19) -0.0617(2) 0.0226(9) Uani 1 1 d . . . 
C14 C 0.4560(4) 0.32935(18) 0.0024(2) 0.0233(9) Uani 1 1 d . . . 
H14 H 0.4802 0.3164 0.0633 0.028 Uiso 1 1 calc R . . 
C15 C 0.4918(4) 0.39671(19) -0.0241(2) 0.0262(9) Uani 1 1 d . . . 
H15 H 0.5419 0.4296 0.0194 0.031 Uiso 1 1 calc R . . 
C16 C 0.4559(4) 0.41652(19) -0.1123(2) 0.0267(9) Uani 1 1 d . . . 
H16 H 0.4809 0.4627 -0.1293 0.032 Uiso 1 1 calc R . . 
C17 C 0.3837(4) 0.36910(19) -0.1757(3) 0.0311(10) Uani 1 1 d . . . 
H17 H 0.3588 0.3826 -0.2365 0.037 Uiso 1 1 calc R . . 
C18 C 0.3471(4) 0.30142(19) -0.1506(2) 0.0271(9) Uani 1 1 d . . . 
H18 H 0.2967 0.2689 -0.1942 0.033 Uiso 1 1 calc R . . 
C19 C 0.2010(4) -0.08195(18) -0.0265(2) 0.0207(9) Uani 1 1 d . . . 
C20 C 0.0642(4) -0.10833(19) -0.0378(2) 0.0245(9) Uani 1 1 d . . . 
H20 H -0.0030 -0.0824 -0.0147 0.029 Uiso 1 1 calc R . . 
C21 C 0.0241(4) -0.17251(19) -0.0827(2) 0.0269(9) Uani 1 1 d . . . 
H21 H -0.0707 -0.1896 -0.0909 0.032 Uiso 1 1 calc R . . 
C22 C 0.1210(4) -0.21157(19) -0.1153(2) 0.0256(9) Uani 1 1 d . . . 
H22 H 0.0933 -0.2556 -0.1454 0.031 Uiso 1 1 calc R . . 
C23 C 0.2587(4) -0.18607(19) -0.1040(2) 0.0251(9) Uani 1 1 d . . . 
H23 H 0.3261 -0.2129 -0.1258 0.030 Uiso 1 1 calc R . . 
C24 C 0.2981(4) -0.12099(19) -0.0606(2) 0.0243(9) Uani 1 1 d . . . 
H24 H 0.3920 -0.1031 -0.0542 0.029 Uiso 1 1 calc R . . 
C25 C 0.2605(4) 0.06158(18) -0.1220(2) 0.0208(8) Uani 1 1 d . . . 
C26 C 0.1268(4) 0.06802(18) -0.1809(2) 0.0228(9) Uani 1 1 d . . . 
H26 H 0.0435 0.0594 -0.1608 0.027 Uiso 1 1 calc R . . 
C27 C 0.1142(4) 0.08692(18) -0.2689(2) 0.0265(9) Uani 1 1 d . . . 
H27 H 0.0225 0.0920 -0.3084 0.032 Uiso 1 1 calc R . . 
C28 C 0.2355(4) 0.09831(19) -0.2991(2) 0.0301(10) Uani 1 1 d . . . 
H28 H 0.2269 0.1120 -0.3590 0.036 Uiso 1 1 calc R . . 
C29 C 0.3673(4) 0.0898(2) -0.2426(3) 0.0347(10) Uani 1 1 d . . . 
H29 H 0.4503 0.0965 -0.2637 0.042 Uiso 1 1 calc R . . 
C30 C 0.3805(4) 0.0714(2) -0.1543(2) 0.0302(10) Uani 1 1 d . . . 
H30 H 0.4727 0.0655 -0.1157 0.036 Uiso 1 1 calc R . . 
C31 C 0.4569(4) 0.26014(19) 0.3179(2) 0.0290(10) Uani 1 1 d . . . 
H31A H 0.5198 0.2346 0.3677 0.043 Uiso 1 1 calc R . . 
H31B H 0.4462 0.3100 0.3351 0.043 Uiso 1 1 calc R . . 
H31C H 0.4984 0.2591 0.2666 0.043 Uiso 1 1 calc R . . 
C32 C 0.2475(4) 0.2254(2) 0.3951(2) 0.0291(9) Uani 1 1 d . . . 
H32A H 0.1566 0.2015 0.3928 0.044 Uiso 1 1 calc R . . 
H32B H 0.2405 0.2761 0.4098 0.044 Uiso 1 1 calc R . . 
H32C H 0.3233 0.2026 0.4405 0.044 Uiso 1 1 calc R . . 
N1 N 0.2721(3) -0.01096(15) 0.26258(18) 0.0235(7) Uani 1 1 d . . . 
H1A H 0.2598 0.0358 0.2610 0.028 Uiso 1 1 calc R . . 
N2 N 0.3048(3) 0.07594(14) 0.11877(18) 0.0209(7) Uani 1 1 d . . . 
H2A H 0.3236 0.0992 0.1696 0.025 Uiso 1 1 calc R . . 
N3 N 0.3451(3) 0.21133(15) -0.04121(18) 0.0249(7) Uani 1 1 d . . . 
H3A H 0.3139 0.1830 -0.0872 0.030 Uiso 1 1 calc R . . 
O1 O 0.2551(3) -0.10868(13) 0.17172(15) 0.0291(7) Uani 1 1 d . . . 
O2 O 0.3836(3) 0.21525(13) 0.10959(15) 0.0293(6) Uani 1 1 d . . . 
O3 O 0.3190(3) 0.13878(12) 0.28113(16) 0.0312(7) Uani 1 1 d . . . 
S1 S 0.28782(10) 0.21803(5) 0.28988(6) 0.0247(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 C2 1.391(5) . ? 
C1 C6 1.394(5) . ? 
C2 C3 1.378(5) . ? 
C3 C4 1.376(5) . ? 
C4 C5 1.379(5) . ? 
C5 C6 1.398(5) . ? 
C6 N1 1.417(4) . ? 
C7 O1 1.243(4) . ? 
C7 N1 1.353(4) . ? 
C7 C8 1.485(5) . ? 
C8 N2 1.372(4) . ? 
C8 C9 1.387(4) . ? 
C9 C10 1.417(5) . ? 
C9 C19 1.495(5) . ? 
C10 C11 1.394(5) . ? 
C10 C25 1.488(5) . ? 
C11 N2 1.361(4) . ? 
C11 C12 1.484(5) . ? 
C12 O2 1.235(4) . ? 
C12 N3 1.360(4) . ? 
C13 C14 1.389(5) . ? 
C13 C18 1.389(5) . ? 
C13 N3 1.419(4) . ? 
C14 C15 1.392(5) . ? 
C15 C16 1.379(5) . ? 
C16 C17 1.378(5) . ? 
C17 C18 1.393(5) . ? 
C19 C20 1.383(5) . ? 
C19 C24 1.395(5) . ? 
C20 C21 1.391(5) . ? 
C21 C22 1.381(5) . ? 
C22 C23 1.385(5) . ? 
C23 C24 1.395(5) . ? 
C25 C30 1.390(5) . ? 
C25 C26 1.392(5) . ? 
C26 C27 1.390(5) . ? 
C27 C28 1.386(5) . ? 
C28 C29 1.366(5) . ? 
C29 C30 1.390(5) . ? 
C31 S1 1.769(4) . ? 
C32 S1 1.781(3) . ? 
O3 S1 1.521(2) . ? 
 
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 
C2 C1 C6 119.0(3) . . ? 
C3 C2 C1 121.5(3) . . ? 
C4 C3 C2 119.1(3) . . ? 
C3 C4 C5 120.6(3) . . ? 
C4 C5 C6 120.5(3) . . ? 
C1 C6 C5 119.1(3) . . ? 
C1 C6 N1 124.4(3) . . ? 
C5 C6 N1 116.4(3) . . ? 
O1 C7 N1 123.4(3) . . ? 
O1 C7 C8 119.7(3) . . ? 
N1 C7 C8 116.9(3) . . ? 
N2 C8 C9 108.2(3) . . ? 
N2 C8 C7 122.3(3) . . ? 
C9 C8 C7 129.2(3) . . ? 
C8 C9 C10 107.1(3) . . ? 
C8 C9 C19 128.0(3) . . ? 
C10 C9 C19 124.9(3) . . ? 
C11 C10 C9 106.8(3) . . ? 
C11 C10 C25 125.4(3) . . ? 
C9 C10 C25 127.7(3) . . ? 
N2 C11 C10 108.5(3) . . ? 
N2 C11 C12 116.5(3) . . ? 
C10 C11 C12 135.0(3) . . ? 
O2 C12 N3 123.2(3) . . ? 
O2 C12 C11 120.3(3) . . ? 
N3 C12 C11 116.5(3) . . ? 
C14 C13 C18 120.0(3) . . ? 
C14 C13 N3 123.0(3) . . ? 
C18 C13 N3 117.0(3) . . ? 
C13 C14 C15 119.0(3) . . ? 
C16 C15 C14 121.1(3) . . ? 
C17 C16 C15 119.8(3) . . ? 
C16 C17 C18 120.0(3) . . ? 
C13 C18 C17 120.1(3) . . ? 
C20 C19 C24 118.8(3) . . ? 
C20 C19 C9 121.4(3) . . ? 
C24 C19 C9 119.7(3) . . ? 
C19 C20 C21 120.5(3) . . ? 
C22 C21 C20 120.6(3) . . ? 
C21 C22 C23 119.6(3) . . ? 
C22 C23 C24 119.9(3) . . ? 
C23 C24 C19 120.6(4) . . ? 
C30 C25 C26 118.3(3) . . ? 
C30 C25 C10 121.3(3) . . ? 
C26 C25 C10 120.1(3) . . ? 
C27 C26 C25 120.6(3) . . ? 
C28 C27 C26 120.0(4) . . ? 
C29 C28 C27 119.9(4) . . ? 
C28 C29 C30 120.3(4) . . ? 
C25 C30 C29 120.8(4) . . ? 
C7 N1 C6 129.0(3) . . ? 
C11 N2 C8 109.3(3) . . ? 
C12 N3 C13 129.5(3) . . ? 
O3 S1 C31 105.10(17) . . ? 
O3 S1 C32 104.54(16) . . ? 
C31 S1 C32 98.13(17) . . ? 
 
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 
N1 H1A O3  0.88 2.01 2.831(4) 156.0 . 
N2 H2A O3  0.88 1.90 2.757(4) 165.3 . 
 
_diffrn_measured_fraction_theta_max    0.992 
_diffrn_reflns_theta_full              24.70 
_diffrn_measured_fraction_theta_full   0.992 
_refine_diff_density_max    0.297 
_refine_diff_density_min   -0.335 
_refine_diff_density_rms    0.072 
