 
data_samanta5 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          
 'C20 H14 N4 S' 
_chemical_formula_sum 
 'C20 H14 N4 S' 
_chemical_formula_weight          342.41 
 
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' 
 
_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    'P 21/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                    11.9769(12) 
_cell_length_b                    6.7970(7) 
_cell_length_c                    19.8608(19) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.491(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1616.7(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     186(2) 
_cell_measurement_reflns_used     4323
_cell_measurement_theta_min       3
_cell_measurement_theta_max       23 
 
_exptl_crystal_description        rod
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.60
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.08
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.407 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              712 
_exptl_absorpt_coefficient_mu     0.210 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.843
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'SADABS (Sheldrick, 2000)'
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       186(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'normal-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   Siemens_SMART_1K_CCD
_diffrn_measurement_method        ω
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          111
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   1200
_diffrn_standards_decay_%         0.0
_diffrn_reflns_number             16828 
_diffrn_reflns_av_R_equivalents   0.1127 
_diffrn_reflns_av_sigmaI/netI     0.1040 
_diffrn_reflns_limit_h_min        -14 
_diffrn_reflns_limit_h_max        14 
_diffrn_reflns_limit_k_min        -8 
_diffrn_reflns_limit_k_max        8 
_diffrn_reflns_limit_l_min        -24 
_diffrn_reflns_limit_l_max        24 
_diffrn_reflns_theta_min          1.03 
_diffrn_reflns_theta_max          26.00 
_reflns_number_total              3151 
_reflns_number_gt                 1945 
_reflns_threshold_expression      I>2σ(I) 
 
_computing_data_collection        'SMART (Siemens, 1995)'
_computing_cell_refinement        'SAINT (Siemens, 1995)'
_computing_data_reduction         'SAINT (Siemens, 1995)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ? 
_computing_publication_material   'SHELXL-97 (Sheldrick, 2008)'
 
_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)+(0.064P)²+0.14P] 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      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3151 
_refine_ls_number_parameters      227 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1359 
_refine_ls_R_factor_gt            0.0729 
_refine_ls_wR_factor_ref          0.1535 
_refine_ls_wR_factor_gt           0.1319 
_refine_ls_goodness_of_fit_ref    1.043 
_refine_ls_restrained_S_all       1.043 
_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 
S1 S 0.55857(9) 0.71234(17) 0.25431(6) 0.0342(3) Uani 1 1 d . . . 
N3 N 0.6692(3) 0.7107(5) 0.36455(17) 0.0277(8) Uani 1 1 d . . . 
N2 N 0.8514(3) 0.7245(5) 0.33790(17) 0.0308(9) Uani 1 1 d . . . 
N1 N 0.7025(3) 0.7280(5) 0.25223(18) 0.0321(9) Uani 1 1 d . . . 
N4 N 0.4772(3) 0.7150(5) 0.38433(17) 0.0280(8) Uani 1 1 d . . . 
C8 C 0.5582(4) 0.7105(6) 0.3445(2) 0.0277(9) Uani 1 1 d . . . 
C2 C 0.8387(4) 0.7149(6) 0.4087(2) 0.0285(10) Uani 1 1 d . . . 
C9 C 0.7595(4) 0.7206(6) 0.1896(2) 0.0293(10) Uani 1 1 d . . . 
C10 C 0.8757(3) 0.7124(6) 0.1874(2) 0.0322(10) Uani 1 1 d . . . 
H10A H 0.9182 0.7109 0.2280 0.039 Uiso 1 1 calc R . . 
C1 C 0.7495(4) 0.7211(6) 0.3154(2) 0.0263(10) Uani 1 1 d . . . 
C7 C 0.7263(3) 0.7067(6) 0.4260(2) 0.0267(10) Uani 1 1 d . . . 
C15 C 0.3676(3) 0.7099(6) 0.3590(2) 0.0278(10) Uani 1 1 d . . . 
C12 C 0.8679(4) 0.7074(7) 0.0670(2) 0.0376(12) Uani 1 1 d . . . 
H12A H 0.9051 0.7037 0.0250 0.045 Uiso 1 1 calc R . . 
C5 C 0.7718(4) 0.6861(7) 0.5405(2) 0.0391(12) Uani 1 1 d . . . 
H5A H 0.7509 0.6762 0.5865 0.047 Uiso 1 1 calc R . . 
C13 C 0.7531(4) 0.7137(7) 0.0689(2) 0.0397(12) Uani 1 1 d . . . 
H13A H 0.7109 0.7130 0.0282 0.048 Uiso 1 1 calc R . . 
C3 C 0.9190(4) 0.7094(7) 0.4585(2) 0.0368(11) Uani 1 1 d . . . 
H3A H 0.9961 0.7152 0.4479 0.044 Uiso 1 1 calc R . . 
C14 C 0.6992(4) 0.7211(6) 0.1303(2) 0.0371(12) Uani 1 1 d . . . 
H14A H 0.6200 0.7264 0.1315 0.045 Uiso 1 1 calc R . . 
C20 C 0.3304(4) 0.5730(6) 0.3113(2) 0.0338(11) Uani 1 1 d . . . 
H20A H 0.3817 0.4826 0.2922 0.041 Uiso 1 1 calc R . . 
C6 C 0.6889(4) 0.6911(6) 0.4917(2) 0.0326(11) Uani 1 1 d . . . 
H6A H 0.6118 0.6844 0.5023 0.039 Uiso 1 1 calc R . . 
C18 C 0.1447(4) 0.6991(8) 0.3189(2) 0.0440(13) Uani 1 1 d . . . 
H18A H 0.0683 0.6939 0.3059 0.053 Uiso 1 1 calc R . . 
C19 C 0.2196(4) 0.5685(7) 0.2918(2) 0.0381(12) Uani 1 1 d . . . 
H19A H 0.1949 0.4747 0.2595 0.046 Uiso 1 1 calc R . . 
C11 C 0.9287(4) 0.7064(6) 0.1259(2) 0.0362(11) Uani 1 1 d . . . 
H11A H 1.0079 0.7016 0.1244 0.043 Uiso 1 1 calc R . . 
C4 C 0.8839(4) 0.6949(7) 0.5248(2) 0.0417(12) Uani 1 1 d . . . 
H4A H 0.9380 0.6911 0.5600 0.050 Uiso 1 1 calc R . . 
C16 C 0.2907(3) 0.8414(7) 0.3851(2) 0.0320(11) Uani 1 1 d . . . 
H16A H 0.3143 0.9358 0.4175 0.038 Uiso 1 1 calc R . . 
C17 C 0.1806(4) 0.8367(7) 0.3646(2) 0.0407(12) Uani 1 1 d . . . 
H17A H 0.1292 0.9295 0.3822 0.049 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 N1 1.728(3) . ? 
S1 C8 1.791(4) . ? 
N3 C1 1.379(5) . ? 
N3 C8 1.385(6) . ? 
N3 C7 1.395(5) . ? 
N2 C1 1.297(5) . ? 
N2 C2 1.418(5) . ? 
N1 C1 1.371(6) . ? 
N1 C9 1.425(5) . ? 
N4 C8 1.257(5) . ? 
N4 C15 1.402(5) . ? 
C2 C3 1.373(6) . ? 
C2 C7 1.393(6) . ? 
C9 C14 1.376(6) . ? 
C9 C10 1.393(6) . ? 
C10 C11 1.382(6) . ? 
C10 H10A 0.9500 . ? 
C7 C6 1.386(6) . ? 
C15 C16 1.387(6) . ? 
C15 C20 1.399(6) . ? 
C12 C11 1.372(6) . ? 
C12 C13 1.377(6) . ? 
C12 H12A 0.9500 . ? 
C5 C6 1.383(6) . ? 
C5 C4 1.383(6) . ? 
C5 H5A 0.9500 . ? 
C13 C14 1.386(6) . ? 
C13 H13A 0.9500 . ? 
C3 C4 1.389(6) . ? 
C3 H3A 0.9500 . ? 
C14 H14A 0.9500 . ? 
C20 C19 1.379(6) . ? 
C20 H20A 0.9500 . ? 
C6 H6A 0.9500 . ? 
C18 C17 1.370(6) . ? 
C18 C19 1.374(6) . ? 
C18 H18A 0.9500 . ? 
C19 H19A 0.9500 . ? 
C11 H11A 0.9500 . ? 
C4 H4A 0.9500 . ? 
C16 C17 1.377(6) . ? 
C16 H16A 0.9500 . ? 
C17 H17A 0.9500 . ? 
 
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 
N1 S1 C8 92.0(2) . . ? 
C1 N3 C8 118.0(4) . . ? 
C1 N3 C7 106.3(3) . . ? 
C8 N3 C7 135.6(4) . . ? 
C1 N2 C2 103.5(3) . . ? 
C1 N1 C9 126.9(3) . . ? 
C1 N1 S1 112.2(3) . . ? 
C9 N1 S1 120.3(3) . . ? 
C8 N4 C15 119.9(4) . . ? 
N4 C8 N3 124.3(4) . . ? 
N4 C8 S1 129.6(4) . . ? 
N3 C8 S1 106.1(3) . . ? 
C3 C2 C7 119.6(4) . . ? 
C3 C2 N2 129.4(4) . . ? 
C7 C2 N2 111.0(4) . . ? 
C14 C9 C10 119.3(4) . . ? 
C14 C9 N1 119.6(4) . . ? 
C10 C9 N1 121.0(4) . . ? 
C11 C10 C9 119.7(4) . . ? 
C11 C10 H10A 120.1 . . ? 
C9 C10 H10A 120.1 . . ? 
N2 C1 N1 133.9(4) . . ? 
N2 C1 N3 114.6(4) . . ? 
N1 C1 N3 111.5(4) . . ? 
C6 C7 C2 123.8(4) . . ? 
C6 C7 N3 131.6(4) . . ? 
C2 C7 N3 104.6(3) . . ? 
C16 C15 C20 118.3(4) . . ? 
C16 C15 N4 118.2(4) . . ? 
C20 C15 N4 123.4(4) . . ? 
C11 C12 C13 120.0(4) . . ? 
C11 C12 H12A 120.0 . . ? 
C13 C12 H12A 120.0 . . ? 
C6 C5 C4 122.2(4) . . ? 
C6 C5 H5A 118.9 . . ? 
C4 C5 H5A 118.9 . . ? 
C12 C13 C14 119.8(5) . . ? 
C12 C13 H13A 120.1 . . ? 
C14 C13 H13A 120.1 . . ? 
C2 C3 C4 118.0(4) . . ? 
C2 C3 H3A 121.0 . . ? 
C4 C3 H3A 121.0 . . ? 
C9 C14 C13 120.6(5) . . ? 
C9 C14 H14A 119.7 . . ? 
C13 C14 H14A 119.7 . . ? 
C19 C20 C15 120.3(4) . . ? 
C19 C20 H20A 119.9 . . ? 
C15 C20 H20A 119.9 . . ? 
C5 C6 C7 115.2(4) . . ? 
C5 C6 H6A 122.4 . . ? 
C7 C6 H6A 122.4 . . ? 
C17 C18 C19 119.9(4) . . ? 
C17 C18 H18A 120.1 . . ? 
C19 C18 H18A 120.1 . . ? 
C18 C19 C20 120.4(4) . . ? 
C18 C19 H19A 119.8 . . ? 
C20 C19 H19A 119.8 . . ? 
C12 C11 C10 120.6(4) . . ? 
C12 C11 H11A 119.7 . . ? 
C10 C11 H11A 119.7 . . ? 
C5 C4 C3 121.3(4) . . ? 
C5 C4 H4A 119.4 . . ? 
C3 C4 H4A 119.4 . . ? 
C17 C16 C15 120.8(4) . . ? 
C17 C16 H16A 119.6 . . ? 
C15 C16 H16A 119.6 . . ? 
C18 C17 C16 120.4(4) . . ? 
C18 C17 H17A 119.8 . . ? 
C16 C17 H17A 119.8 . . ? 
 
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 
C8 S1 N1 C1 3.3(3) . . . . ? 
C8 S1 N1 C9 175.3(3) . . . . ? 
C15 N4 C8 N3 -178.6(4) . . . . ? 
C15 N4 C8 S1 4.1(6) . . . . ? 
C1 N3 C8 N4 -174.9(4) . . . . ? 
C7 N3 C8 N4 3.4(7) . . . . ? 
C1 N3 C8 S1 2.9(4) . . . . ? 
C7 N3 C8 S1 -178.8(4) . . . . ? 
N1 S1 C8 N4 174.3(4) . . . . ? 
N1 S1 C8 N3 -3.3(3) . . . . ? 
C1 N2 C2 C3 178.5(5) . . . . ? 
C1 N2 C2 C7 -0.2(5) . . . . ? 
C1 N1 C9 C14 177.3(4) . . . . ? 
S1 N1 C9 C14 6.6(5) . . . . ? 
C1 N1 C9 C10 -2.5(6) . . . . ? 
S1 N1 C9 C10 -173.2(3) . . . . ? 
C14 C9 C10 C11 0.5(6) . . . . ? 
N1 C9 C10 C11 -179.6(4) . . . . ? 
C2 N2 C1 N1 179.2(4) . . . . ? 
C2 N2 C1 N3 0.2(5) . . . . ? 
C9 N1 C1 N2 7.3(7) . . . . ? 
S1 N1 C1 N2 178.7(4) . . . . ? 
C9 N1 C1 N3 -173.6(4) . . . . ? 
S1 N1 C1 N3 -2.2(4) . . . . ? 
C8 N3 C1 N2 178.7(4) . . . . ? 
C7 N3 C1 N2 -0.1(5) . . . . ? 
C8 N3 C1 N1 -0.5(5) . . . . ? 
C7 N3 C1 N1 -179.3(3) . . . . ? 
C3 C2 C7 C6 -0.6(7) . . . . ? 
N2 C2 C7 C6 178.2(4) . . . . ? 
C3 C2 C7 N3 -178.6(4) . . . . ? 
N2 C2 C7 N3 0.2(5) . . . . ? 
C1 N3 C7 C6 -177.9(4) . . . . ? 
C8 N3 C7 C6 3.6(8) . . . . ? 
C1 N3 C7 C2 -0.1(4) . . . . ? 
C8 N3 C7 C2 -178.6(4) . . . . ? 
C8 N4 C15 C16 -134.3(4) . . . . ? 
C8 N4 C15 C20 48.9(6) . . . . ? 
C11 C12 C13 C14 0.7(7) . . . . ? 
C7 C2 C3 C4 0.2(7) . . . . ? 
N2 C2 C3 C4 -178.4(4) . . . . ? 
C10 C9 C14 C13 -0.1(6) . . . . ? 
N1 C9 C14 C13 -179.9(4) . . . . ? 
C12 C13 C14 C9 -0.5(7) . . . . ? 
C16 C15 C20 C19 -0.9(6) . . . . ? 
N4 C15 C20 C19 175.8(4) . . . . ? 
C4 C5 C6 C7 -0.3(7) . . . . ? 
C2 C7 C6 C5 0.6(6) . . . . ? 
N3 C7 C6 C5 178.1(4) . . . . ? 
C17 C18 C19 C20 1.1(7) . . . . ? 
C15 C20 C19 C18 0.3(6) . . . . ? 
C13 C12 C11 C10 -0.2(7) . . . . ? 
C9 C10 C11 C12 -0.4(7) . . . . ? 
C6 C5 C4 C3 0.0(7) . . . . ? 
C2 C3 C4 C5 0.1(7) . . . . ? 
C20 C15 C16 C17 0.2(6) . . . . ? 
N4 C15 C16 C17 -176.8(4) . . . . ? 
C19 C18 C17 C16 -1.9(7) . . . . ? 
C15 C16 C17 C18 1.3(7) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.990 
_diffrn_reflns_theta_full              26.00 
_diffrn_measured_fraction_theta_full   0.990 
_refine_diff_density_max    0.427 
_refine_diff_density_min   -0.334 
_refine_diff_density_rms    0.059 
