 
data_190501b 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C19.50 H19 Cl N2 O3 S2' 
_chemical_formula_weight          428.94 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 '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'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'S'  'S'   0.3331   0.5567 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Cl'  'Cl'   0.3639   0.7018 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            Monoclinic 
_symmetry_space_group_name_H-M    C2 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y, -z' 
 'x+1/2, y+1/2, z' 
 '-x+1/2, y+1/2, -z' 
 
_cell_length_a                    23.3237(11) 
_cell_length_b                    6.7691(3) 
_cell_length_c                    13.9148(5) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  116.158(4) 
_cell_angle_gamma                 90.00 
_cell_volume                      1971.87(15) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     2623 
_cell_measurement_theta_min       4.1250  
_cell_measurement_theta_max       72.2400 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.18 
_exptl_crystal_size_mid           0.17 
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.445 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              892 
_exptl_absorpt_coefficient_mu     3.895 
_exptl_absorpt_correction_type    multi-scan  
_exptl_absorpt_correction_T_min   0.5407 
_exptl_absorpt_correction_T_max   0.8291 
_exptl_absorpt_process_details    sadabs
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Xcalibur, Eos, Gemini' 
_diffrn_detector 'CCD plate' 
_diffrn_detector_type Eos 
_diffrn_detector_area_resol_mean 8.1281 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             6575 
_diffrn_reflns_av_R_equivalents   0.0398 
_diffrn_reflns_av_sigmaI/netI     0.0561 
_diffrn_reflns_limit_h_min        -18 
_diffrn_reflns_limit_h_max        27 
_diffrn_reflns_limit_k_min        -8 
_diffrn_reflns_limit_k_max        8 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          3.54 
_diffrn_reflns_theta_max          66.04 
_reflns_number_total              3320 
_reflns_number_gt                 2790 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Bruker FRAMBO' 
_computing_cell_refinement        'Bruker FRAMBO' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
 
_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)+(0.1135P)²+1.4810P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_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(4) 
_refine_ls_number_reflns          3320 
_refine_ls_number_parameters      251 
_refine_ls_number_restraints      19 
_refine_ls_R_factor_all           0.0767 
_refine_ls_R_factor_gt            0.0649 
_refine_ls_wR_factor_ref          0.1859 
_refine_ls_wR_factor_gt           0.1728 
_refine_ls_goodness_of_fit_ref    1.047 
_refine_ls_restrained_S_all       1.070 
_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 
N1 N 0.47212(18) 0.1119(7) 0.1109(3) 0.0394(10) Uani 1 1 d . . . 
H1 H 0.4647 0.0260 0.0613 0.047 Uiso 1 1 calc R . . 
N2 N 0.5049(2) 0.2877(7) 0.3012(3) 0.0424(10) Uani 1 1 d . . . 
H2 H 0.5209 0.3117 0.3687 0.051 Uiso 1 1 calc R . . 
O1 O 0.56950(18) 0.1644(6) 0.1200(3) 0.0473(9) Uani 1 1 d . . . 
O2 O 0.41389(19) 0.1906(7) 0.3048(3) 0.0549(10) Uani 1 1 d . . . 
O3 O 0.6032(2) 0.2759(7) 0.5173(3) 0.0563(11) Uani 1 1 d . . . 
H3 H 0.6037 0.2515 0.5754 0.084 Uiso 1 1 calc R . . 
S1 S 0.36880(7) 0.3573(2) 0.05571(11) 0.0530(4) Uani 1 1 d . . . 
S2 S 0.52119(8) 0.5846(2) 0.19174(12) 0.0543(4) Uani 1 1 d . . . 
Cl1 Cl 0.4504(2) 0.6846(6) 0.3845(3) 0.1574(15) Uani 1 1 d U . . 
C1 C 0.4205(2) 0.1533(8) 0.1394(4) 0.0405(12) Uani 1 1 d . . . 
C2 C 0.3756(2) -0.0298(9) 0.1127(4) 0.0432(12) Uani 1 1 d . . . 
H2A H 0.3998 -0.1505 0.1214 0.052 Uiso 1 1 calc R . . 
H2B H 0.3552 -0.0350 0.1602 0.052 Uiso 1 1 calc R . . 
C3 C 0.3258(2) -0.0079(10) -0.0024(4) 0.0482(14) Uani 1 1 d . . . 
C4 C 0.3162(3) 0.1874(10) -0.0382(4) 0.0500(14) Uani 1 1 d . . . 
C5 C 0.2700(3) 0.2350(12) -0.1391(5) 0.0617(17) Uani 1 1 d . . . 
H5 H 0.2637 0.3651 -0.1630 0.074 Uiso 1 1 calc R . . 
C6 C 0.2335(3) 0.0839(15) -0.2034(5) 0.071(2) Uani 1 1 d . . . 
H6 H 0.2013 0.1142 -0.2709 0.086 Uiso 1 1 calc R . . 
C7 C 0.2431(3) -0.1119(15) -0.1707(5) 0.073(2) Uani 1 1 d . . . 
H7 H 0.2191 -0.2118 -0.2168 0.087 Uiso 1 1 calc R . . 
C8 C 0.2895(3) -0.1571(11) -0.0669(5) 0.0580(15) Uani 1 1 d . . . 
H8 H 0.2954 -0.2867 -0.0423 0.070 Uiso 1 1 calc R . . 
C9 C 0.5304(2) 0.1950(8) 0.1548(4) 0.0375(11) Uani 1 1 d . . . 
C10 C 0.5449(2) 0.3322(8) 0.2489(4) 0.0399(11) Uani 1 1 d . . . 
C11 C 0.4470(3) 0.2149(8) 0.2568(4) 0.0430(12) Uani 1 1 d . . . 
C12 C 0.6159(2) 0.3330(8) 0.3298(4) 0.0435(12) Uani 1 1 d . . . 
H12A H 0.6413 0.3549 0.2911 0.052 Uiso 1 1 calc R . . 
H12B H 0.6234 0.4435 0.3782 0.052 Uiso 1 1 calc R . . 
C13 C 0.6390(2) 0.1482(9) 0.3948(4) 0.0419(12) Uani 1 1 d . . . 
C14 C 0.6346(2) 0.1293(8) 0.4917(4) 0.0432(12) Uani 1 1 d . . . 
C15 C 0.6609(3) -0.0337(11) 0.5574(5) 0.0590(16) Uani 1 1 d . . . 
H15 H 0.6580 -0.0452 0.6217 0.071 Uiso 1 1 calc R . . 
C16 C 0.6911(3) -0.1766(11) 0.5276(6) 0.0676(18) Uani 1 1 d . . . 
H16 H 0.7087 -0.2846 0.5722 0.081 Uiso 1 1 calc R . . 
C17 C 0.6959(3) -0.1639(11) 0.4322(6) 0.0615(16) Uani 1 1 d . . . 
H17 H 0.7160 -0.2630 0.4120 0.074 Uiso 1 1 calc R . . 
C18 C 0.6701(3) 0.0008(10) 0.3670(4) 0.0484(13) Uani 1 1 d . . . 
H18 H 0.6738 0.0118 0.3033 0.058 Uiso 1 1 calc R . . 
C19 C 0.5752(4) 0.6388(11) 0.1353(6) 0.072(2) Uani 1 1 d . . . 
H19A H 0.6184 0.6258 0.1895 0.108 Uiso 1 1 calc R . . 
H19B H 0.5681 0.7714 0.1081 0.108 Uiso 1 1 calc R . . 
H19C H 0.5680 0.5482 0.0780 0.108 Uiso 1 1 calc R . . 
C20 C 0.5000 0.811(4) 0.5000 0.181(7) Uani 1 2 d SU . . 
H20A H 0.4730 0.8963 0.5185 0.217 Uiso 0.50 1 calc PR . . 
H20B H 0.5270 0.8963 0.4815 0.217 Uiso 0.50 1 calc PR . . 
 
 
_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 
N1 C9 1.344(6) . ? 
N1 C1 1.451(6) . ? 
N1 H1 0.8600 . ? 
N2 C11 1.309(7) . ? 
N2 C10 1.446(6) . ? 
N2 H2 0.8600 . ? 
O1 C9 1.223(6) . ? 
O2 C11 1.235(6) . ? 
O3 C14 1.370(7) . ? 
O3 H3 0.8200 . ? 
S1 C4 1.767(7) . ? 
S1 C1 1.865(5) . ? 
S2 C19 1.791(7) . ? 
S2 C10 1.863(5) . ? 
Cl1 C20 1.735(13) . ? 
C1 C11 1.528(7) . ? 
C1 C2 1.558(8) . ? 
C2 C3 1.515(7) . ? 
C2 H2A 0.9700 . ? 
C2 H2B 0.9700 . ? 
C3 C8 1.368(9) . ? 
C3 C4 1.396(9) . ? 
C4 C5 1.379(8) . ? 
C5 C6 1.379(11) . ? 
C5 H5 0.9300 . ? 
C6 C7 1.387(12) . ? 
C6 H6 0.9300 . ? 
C7 C8 1.404(9) . ? 
C7 H7 0.9300 . ? 
C8 H8 0.9300 . ? 
C9 C10 1.516(7) . ? 
C10 C12 1.538(7) . ? 
C12 C13 1.498(8) . ? 
C12 H12A 0.9700 . ? 
C12 H12B 0.9700 . ? 
C13 C18 1.385(8) . ? 
C13 C14 1.404(7) . ? 
C14 C15 1.391(8) . ? 
C15 C16 1.364(10) . ? 
C15 H15 0.9300 . ? 
C16 C17 1.383(10) . ? 
C16 H16 0.9300 . ? 
C17 C18 1.396(9) . ? 
C17 H17 0.9300 . ? 
C18 H18 0.9300 . ? 
C19 H19A 0.9600 . ? 
C19 H19B 0.9600 . ? 
C19 H19C 0.9600 . ? 
C20 Cl1 1.735(13) 2_656 ? 
C20 H20A 0.9700 . ? 
C20 H20B 0.9700 . ? 
 
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 
C9 N1 C1 126.2(4) . . ? 
C9 N1 H1 116.9 . . ? 
C1 N1 H1 116.9 . . ? 
C11 N2 C10 127.0(4) . . ? 
C11 N2 H2 116.5 . . ? 
C10 N2 H2 116.5 . . ? 
C14 O3 H3 109.5 . . ? 
C4 S1 C1 91.5(3) . . ? 
C19 S2 C10 103.9(3) . . ? 
N1 C1 C11 110.5(4) . . ? 
N1 C1 C2 109.5(4) . . ? 
C11 C1 C2 112.6(4) . . ? 
N1 C1 S1 111.0(3) . . ? 
C11 C1 S1 108.1(3) . . ? 
C2 C1 S1 105.0(3) . . ? 
C3 C2 C1 107.2(5) . . ? 
C3 C2 H2A 110.3 . . ? 
C1 C2 H2A 110.3 . . ? 
C3 C2 H2B 110.3 . . ? 
C1 C2 H2B 110.3 . . ? 
H2A C2 H2B 108.5 . . ? 
C8 C3 C4 120.6(5) . . ? 
C8 C3 C2 125.8(6) . . ? 
C4 C3 C2 113.4(5) . . ? 
C5 C4 C3 121.0(7) . . ? 
C5 C4 S1 125.3(6) . . ? 
C3 C4 S1 113.7(4) . . ? 
C6 C5 C4 118.0(7) . . ? 
C6 C5 H5 121.0 . . ? 
C4 C5 H5 121.0 . . ? 
C5 C6 C7 122.1(6) . . ? 
C5 C6 H6 118.9 . . ? 
C7 C6 H6 118.9 . . ? 
C6 C7 C8 119.0(7) . . ? 
C6 C7 H7 120.5 . . ? 
C8 C7 H7 120.5 . . ? 
C3 C8 C7 119.2(7) . . ? 
C3 C8 H8 120.4 . . ? 
C7 C8 H8 120.4 . . ? 
O1 C9 N1 122.0(5) . . ? 
O1 C9 C10 121.6(5) . . ? 
N1 C9 C10 116.4(4) . . ? 
N2 C10 C9 111.1(4) . . ? 
N2 C10 C12 111.0(4) . . ? 
C9 C10 C12 113.1(4) . . ? 
N2 C10 S2 105.6(3) . . ? 
C9 C10 S2 106.4(3) . . ? 
C12 C10 S2 109.3(4) . . ? 
O2 C11 N2 123.8(5) . . ? 
O2 C11 C1 119.2(5) . . ? 
N2 C11 C1 117.0(4) . . ? 
C13 C12 C10 115.0(4) . . ? 
C13 C12 H12A 108.5 . . ? 
C10 C12 H12A 108.5 . . ? 
C13 C12 H12B 108.5 . . ? 
C10 C12 H12B 108.5 . . ? 
H12A C12 H12B 107.5 . . ? 
C18 C13 C14 118.1(5) . . ? 
C18 C13 C12 121.8(5) . . ? 
C14 C13 C12 119.8(5) . . ? 
O3 C14 C15 122.4(5) . . ? 
O3 C14 C13 117.2(5) . . ? 
C15 C14 C13 120.4(5) . . ? 
C16 C15 C14 120.1(6) . . ? 
C16 C15 H15 120.0 . . ? 
C14 C15 H15 120.0 . . ? 
C15 C16 C17 121.3(6) . . ? 
C15 C16 H16 119.4 . . ? 
C17 C16 H16 119.4 . . ? 
C16 C17 C18 118.6(6) . . ? 
C16 C17 H17 120.7 . . ? 
C18 C17 H17 120.7 . . ? 
C13 C18 C17 121.6(5) . . ? 
C13 C18 H18 119.2 . . ? 
C17 C18 H18 119.2 . . ? 
S2 C19 H19A 109.5 . . ? 
S2 C19 H19B 109.5 . . ? 
H19A C19 H19B 109.5 . . ? 
S2 C19 H19C 109.5 . . ? 
H19A C19 H19C 109.5 . . ? 
H19B C19 H19C 109.5 . . ? 
Cl1 C20 Cl1 121.0(15) . 2_656 ? 
Cl1 C20 H20A 107.1 . . ? 
Cl1 C20 H20A 107.1 2_656 . ? 
Cl1 C20 H20B 107.1 . . ? 
Cl1 C20 H20B 107.1 2_656 . ? 
H20A C20 H20B 106.8 . . ? 
 
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 
C9 N1 C1 C11 -29.4(7) . . . . ? 
C9 N1 C1 C2 -154.0(5) . . . . ? 
C9 N1 C1 S1 90.6(5) . . . . ? 
C4 S1 C1 N1 93.2(4) . . . . ? 
C4 S1 C1 C11 -145.4(4) . . . . ? 
C4 S1 C1 C2 -25.0(4) . . . . ? 
N1 C1 C2 C3 -88.3(5) . . . . ? 
C11 C1 C2 C3 148.3(4) . . . . ? 
S1 C1 C2 C3 30.9(5) . . . . ? 
C1 C2 C3 C8 159.8(5) . . . . ? 
C1 C2 C3 C4 -24.1(6) . . . . ? 
C8 C3 C4 C5 0.1(8) . . . . ? 
C2 C3 C4 C5 -176.3(5) . . . . ? 
C8 C3 C4 S1 -178.9(4) . . . . ? 
C2 C3 C4 S1 4.8(6) . . . . ? 
C1 S1 C4 C5 -166.3(5) . . . . ? 
C1 S1 C4 C3 12.7(4) . . . . ? 
C3 C4 C5 C6 0.1(9) . . . . ? 
S1 C4 C5 C6 179.0(5) . . . . ? 
C4 C5 C6 C7 -1.7(10) . . . . ? 
C5 C6 C7 C8 3.0(11) . . . . ? 
C4 C3 C8 C7 1.2(9) . . . . ? 
C2 C3 C8 C7 177.1(6) . . . . ? 
C6 C7 C8 C3 -2.7(10) . . . . ? 
C1 N1 C9 O1 -173.7(5) . . . . ? 
C1 N1 C9 C10 5.3(7) . . . . ? 
C11 N2 C10 C9 -30.0(7) . . . . ? 
C11 N2 C10 C12 -156.8(5) . . . . ? 
C11 N2 C10 S2 84.9(6) . . . . ? 
O1 C9 C10 N2 -157.5(5) . . . . ? 
N1 C9 C10 N2 23.5(6) . . . . ? 
O1 C9 C10 C12 -31.9(7) . . . . ? 
N1 C9 C10 C12 149.1(4) . . . . ? 
O1 C9 C10 S2 88.1(5) . . . . ? 
N1 C9 C10 S2 -90.9(5) . . . . ? 
C19 S2 C10 N2 176.5(4) . . . . ? 
C19 S2 C10 C9 -65.3(4) . . . . ? 
C19 S2 C10 C12 57.1(4) . . . . ? 
C10 N2 C11 O2 -175.7(5) . . . . ? 
C10 N2 C11 C1 5.6(8) . . . . ? 
N1 C1 C11 O2 -155.3(5) . . . . ? 
C2 C1 C11 O2 -32.5(7) . . . . ? 
S1 C1 C11 O2 83.0(6) . . . . ? 
N1 C1 C11 N2 23.3(6) . . . . ? 
C2 C1 C11 N2 146.1(5) . . . . ? 
S1 C1 C11 N2 -98.3(5) . . . . ? 
N2 C10 C12 C13 54.7(6) . . . . ? 
C9 C10 C12 C13 -70.9(5) . . . . ? 
S2 C10 C12 C13 170.8(3) . . . . ? 
C10 C12 C13 C18 97.2(6) . . . . ? 
C10 C12 C13 C14 -88.6(6) . . . . ? 
C18 C13 C14 O3 -179.5(5) . . . . ? 
C12 C13 C14 O3 6.1(7) . . . . ? 
C18 C13 C14 C15 0.1(8) . . . . ? 
C12 C13 C14 C15 -174.3(5) . . . . ? 
O3 C14 C15 C16 179.3(6) . . . . ? 
C13 C14 C15 C16 -0.3(9) . . . . ? 
C14 C15 C16 C17 -0.3(11) . . . . ? 
C15 C16 C17 C18 1.0(10) . . . . ? 
C14 C13 C18 C17 0.6(8) . . . . ? 
C12 C13 C18 C17 174.9(5) . . . . ? 
C16 C17 C18 C13 -1.2(9) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              66.04 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    1.074 
_refine_diff_density_min   -0.753 
_refine_diff_density_rms    0.076 
