 
data_test 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety           'C21 H17 Cl N4 O3 S'  
_chemical_formula_sum 
 'C21 H17 Cl N4 O3 S' 
_chemical_formula_weight          440.90 
 
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' 
 'Cl'  'Cl'   0.1484   0.1585 
 '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' 
 
_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    P21/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                    10.901(3) 
_cell_length_b                    5.9316(18) 
_cell_length_c                    30.312(9) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  91.762(5) 
_cell_angle_gamma                 90.00 
_cell_volume                      1959.1(10) 
_cell_formula_units_Z             4 
_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_size_max           0.25 
_exptl_crystal_size_mid           0.23 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.495 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              912 
_exptl_absorpt_coefficient_mu     0.334 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_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   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             10500 
_diffrn_reflns_av_R_equivalents   0.0502 
_diffrn_reflns_av_sigmaI/netI     0.0786 
_diffrn_reflns_limit_h_min        -13 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -7 
_diffrn_reflns_limit_k_max        5 
_diffrn_reflns_limit_l_min        -37 
_diffrn_reflns_limit_l_max        38 
_diffrn_reflns_theta_min          1.34 
_diffrn_reflns_theta_max          27.25 
_reflns_number_total              4289 
_reflns_number_gt                 2227 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_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)+(0.1409P)²+1.3817P] 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_number_reflns          4289 
_refine_ls_number_parameters      271 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1240 
_refine_ls_R_factor_gt            0.0558 
_refine_ls_wR_factor_ref          0.2185 
_refine_ls_wR_factor_gt           0.1595 
_refine_ls_goodness_of_fit_ref    0.844 
_refine_ls_restrained_S_all       0.844 
_refine_ls_shift/su_max           0.036 
_refine_ls_shift/su_mean          0.006 
 
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 0.20582(10) 0.51648(18) 0.36580(4) 0.0495(3) Uani 1 1 d . . . 
Cl1 Cl -0.24718(11) 0.9951(2) 0.15414(4) 0.0581(4) Uani 1 1 d . . . 
O1 O 0.2589(3) 1.0046(5) 0.26598(10) 0.0530(8) Uani 1 1 d . . . 
O3 O -0.2489(2) 0.6364(5) 0.45566(9) 0.0466(7) Uani 1 1 d . . . 
O2 O 0.0331(3) 0.4818(5) 0.43987(10) 0.0546(9) Uani 1 1 d . . . 
N2 N 0.0975(3) 0.9186(6) 0.30891(10) 0.0369(8) Uani 1 1 d . . . 
N4 N -0.0775(3) 0.8013(5) 0.42596(10) 0.0357(7) Uani 1 1 d . . . 
N3 N -0.1136(3) 0.9744(5) 0.39931(11) 0.0390(8) Uani 1 1 d . . . 
C15 C 0.0814(3) 0.6953(7) 0.37676(12) 0.0336(8) Uani 1 1 d . . . 
C16 C 0.0136(3) 0.6467(7) 0.41621(12) 0.0366(9) Uani 1 1 d . . . 
C6 C 0.2228(4) 0.9487(7) 0.30192(13) 0.0390(9) Uani 1 1 d . . . 
C13 C 0.0450(3) 0.8687(7) 0.35013(12) 0.0360(9) Uani 1 1 d . . . 
C7 C 0.0122(3) 0.9443(6) 0.27176(12) 0.0347(9) Uani 1 1 d . . . 
C17 C -0.1447(3) 0.7724(7) 0.46675(12) 0.0381(9) Uani 1 1 d . . . 
H17 H -0.0923 0.6917 0.4884 0.046 Uiso 1 1 calc R . . 
N1 N 0.4195(3) 0.6827(8) 0.39287(12) 0.0559(11) Uani 1 1 d . . . 
C10 C -0.1501(4) 0.9753(7) 0.20069(13) 0.0392(9) Uani 1 1 d . . . 
C4 C 0.3128(3) 0.9204(7) 0.33985(14) 0.0411(10) Uani 1 1 d . . . 
C12 C -0.0668(4) 0.7677(7) 0.26172(13) 0.0437(10) Uani 1 1 d . . . 
H12 H -0.0649 0.6385 0.2791 0.052 Uiso 1 1 calc R . . 
C14 C -0.0557(4) 1.0064(7) 0.36319(13) 0.0405(9) Uani 1 1 d . . . 
H14 H -0.0807 1.1243 0.3448 0.049 Uiso 1 1 calc R . . 
C18 C -0.1849(4) 0.9916(7) 0.48662(14) 0.0479(11) Uani 1 1 d . . . 
H18A H -0.2392 1.0712 0.4660 0.057 Uiso 1 1 calc R . . 
H18B H -0.1141 1.0864 0.4931 0.057 Uiso 1 1 calc R . . 
C5 C 0.3223(4) 0.7267(7) 0.36591(13) 0.0436(10) Uani 1 1 d . . . 
C8 C 0.0086(4) 1.1387(7) 0.24691(13) 0.0399(9) Uani 1 1 d . . . 
H8 H 0.0605 1.2585 0.2541 0.048 Uiso 1 1 calc R . . 
C11 C -0.1486(4) 0.7817(7) 0.22595(14) 0.0458(10) Uani 1 1 d . . . 
H11 H -0.2016 0.6630 0.2191 0.055 Uiso 1 1 calc R . . 
C9 C -0.0731(4) 1.1539(7) 0.21115(13) 0.0414(10) Uani 1 1 d . . . 
H9 H -0.0761 1.2844 0.1941 0.050 Uiso 1 1 calc R . . 
C21 C -0.3105(4) 0.5721(8) 0.49571(16) 0.0540(12) Uani 1 1 d . . . 
H21A H -0.2540 0.4892 0.5150 0.065 Uiso 1 1 calc R . . 
H21B H -0.3793 0.4742 0.4882 0.065 Uiso 1 1 calc R . . 
C1 C 0.4046(4) 1.0840(8) 0.34517(16) 0.0509(11) Uani 1 1 d . . . 
H1 H 0.4012 1.2162 0.3287 0.061 Uiso 1 1 calc R . . 
C20 C -0.3557(4) 0.7770(8) 0.51939(16) 0.0579(13) Uani 1 1 d . . . 
H20A H -0.4187 0.8511 0.5014 0.069 Uiso 1 1 calc R . . 
H20B H -0.3918 0.7318 0.5469 0.069 Uiso 1 1 calc R . . 
C2 C 0.5000(4) 1.0469(10) 0.37515(17) 0.0620(14) Uani 1 1 d . . . 
H2 H 0.5591 1.1572 0.3808 0.074 Uiso 1 1 calc R . . 
C3 C 0.5056(4) 0.8403(11) 0.39680(16) 0.0638(15) Uani 1 1 d . . . 
H3 H 0.5738 0.8109 0.4151 0.077 Uiso 1 1 calc R . . 
C19 C -0.2516(5) 0.9397(8) 0.52894(15) 0.0561(12) Uani 1 1 d . . . 
H19A H -0.1946 0.8743 0.5505 0.067 Uiso 1 1 calc R . . 
H19B H -0.2836 1.0781 0.5412 0.067 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 C15 1.762(4) . ? 
S1 C5 1.780(5) . ? 
Cl1 C10 1.741(4) . ? 
O1 C6 1.216(5) . ? 
O3 C17 1.426(5) . ? 
O3 C21 1.456(5) . ? 
O2 C16 1.228(5) . ? 
N2 C6 1.400(5) . ? 
N2 C13 1.421(5) . ? 
N2 C7 1.446(5) . ? 
N4 N3 1.357(4) . ? 
N4 C16 1.390(5) . ? 
N4 C17 1.466(5) . ? 
N3 C14 1.294(5) . ? 
C15 C13 1.359(5) . ? 
C15 C16 1.453(5) . ? 
C6 C4 1.498(6) . ? 
C13 C14 1.434(5) . ? 
C7 C12 1.384(6) . ? 
C7 C8 1.377(5) . ? 
C17 C18 1.504(6) . ? 
N1 C3 1.328(7) . ? 
N1 C5 1.344(5) . ? 
C10 C11 1.380(6) . ? 
C10 C9 1.383(6) . ? 
C4 C5 1.396(6) . ? 
C4 C1 1.400(6) . ? 
C12 C11 1.385(6) . ? 
C18 C19 1.525(6) . ? 
C8 C9 1.385(5) . ? 
C21 C20 1.502(6) . ? 
C1 C2 1.378(7) . ? 
C20 C19 1.511(7) . ? 
C2 C3 1.391(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 
C15 S1 C5 97.54(18) . . ? 
C17 O3 C21 109.6(3) . . ? 
C6 N2 C13 125.5(3) . . ? 
C6 N2 C7 118.4(3) . . ? 
C13 N2 C7 116.1(3) . . ? 
N3 N4 C16 124.7(3) . . ? 
N3 N4 C17 116.5(3) . . ? 
C16 N4 C17 118.7(3) . . ? 
C14 N3 N4 118.3(3) . . ? 
C13 C15 C16 119.5(3) . . ? 
C13 C15 S1 123.8(3) . . ? 
C16 C15 S1 116.7(3) . . ? 
O2 C16 N4 120.9(3) . . ? 
O2 C16 C15 123.7(3) . . ? 
N4 C16 C15 115.4(3) . . ? 
O1 C6 N2 121.0(4) . . ? 
O1 C6 C4 119.7(4) . . ? 
N2 C6 C4 119.2(3) . . ? 
C15 C13 N2 124.2(3) . . ? 
C15 C13 C14 118.6(3) . . ? 
N2 C13 C14 117.1(3) . . ? 
C12 C7 C8 120.4(4) . . ? 
C12 C7 N2 118.2(3) . . ? 
C8 C7 N2 121.4(4) . . ? 
O3 C17 N4 106.4(3) . . ? 
O3 C17 C18 110.1(3) . . ? 
N4 C17 C18 113.3(3) . . ? 
C3 N1 C5 117.4(4) . . ? 
C11 C10 C9 120.9(4) . . ? 
C11 C10 Cl1 120.1(3) . . ? 
C9 C10 Cl1 118.9(3) . . ? 
C5 C4 C1 117.7(4) . . ? 
C5 C4 C6 124.2(4) . . ? 
C1 C4 C6 117.4(4) . . ? 
C7 C12 C11 120.5(4) . . ? 
N3 C14 C13 123.2(4) . . ? 
C17 C18 C19 108.3(4) . . ? 
N1 C5 C4 123.2(4) . . ? 
N1 C5 S1 114.5(3) . . ? 
C4 C5 S1 122.4(3) . . ? 
C7 C8 C9 119.3(4) . . ? 
C10 C11 C12 118.7(4) . . ? 
C10 C9 C8 120.1(4) . . ? 
O3 C21 C20 110.7(4) . . ? 
C2 C1 C4 119.2(5) . . ? 
C19 C20 C21 110.7(4) . . ? 
C3 C2 C1 118.3(5) . . ? 
N1 C3 C2 123.9(5) . . ? 
C20 C19 C18 110.0(4) . . ? 
 
_diffrn_measured_fraction_theta_max    0.979 
_diffrn_reflns_theta_full              27.25 
_diffrn_measured_fraction_theta_full   0.979 
_refine_diff_density_max    0.305 
_refine_diff_density_min   -0.405 
_refine_diff_density_rms    0.089 
