# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_atk18nov_0m _database_code_depnum_ccdc_archive 'CCDC 875077' #TrackingRef '10532_web_deposit_cif_file_0_Dr.Md.LokmanH.Choudhury_1333629552.ATK18nov_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H11 Cl N4 O S' _chemical_formula_weight 378.83 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 ? _symmetry_space_group_name_H-M ? 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 12.3535(6) _cell_length_b 9.0797(5) _cell_length_c 15.8810(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.010(3) _cell_angle_gamma 90.00 _cell_volume 1742.32(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.355 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 18913 _diffrn_reflns_av_R_equivalents 0.0610 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.36 _reflns_number_total 4301 _reflns_number_gt 3229 _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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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 4301 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1883 _refine_ls_wR_factor_gt 0.1766 _refine_ls_goodness_of_fit_ref 1.297 _refine_ls_restrained_S_all 1.297 _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 S1 S 0.70545(6) 0.27318(5) 0.16226(4) 0.0624(2) Uani 1 1 d . . . N1 N 0.61173(13) 0.53862(16) 0.13061(9) 0.0440(4) Uani 1 1 d . . . C7 C 0.66797(16) 0.43421(18) 0.10129(12) 0.0430(4) Uani 1 1 d . . . C10 C 0.67853(15) 0.56987(18) -0.02741(11) 0.0399(4) Uani 1 1 d . . . C11 C 0.61957(16) 0.68124(19) 0.00336(11) 0.0416(4) Uani 1 1 d . . . C8 C 0.70290(16) 0.44320(19) 0.02209(11) 0.0432(4) Uani 1 1 d . . . C1 C 0.65371(18) 0.3007(2) 0.25701(12) 0.0488(5) Uani 1 1 d . . . C13 C 0.58653(16) 0.66131(19) 0.08294(11) 0.0421(4) Uani 1 1 d . . . C14 C 0.71893(16) 0.58536(19) -0.10961(11) 0.0413(4) Uani 1 1 d . . . C15 C 0.82589(18) 0.6288(3) -0.10602(12) 0.0574(6) Uani 1 1 d . . . H7 H 0.8719 0.6506 -0.0533 0.069 Uiso 1 1 calc R . . C17 C 0.8005(2) 0.6045(3) -0.25910(12) 0.0616(6) Uani 1 1 d . . . H8 H 0.8279 0.6111 -0.3092 0.074 Uiso 1 1 calc R . . C2 C 0.6962(2) 0.4087(2) 0.31489(16) 0.0680(6) Uani 1 1 d . . . H1 H 0.7527 0.4692 0.3045 0.082 Uiso 1 1 calc R . . C6 C 0.5739(2) 0.2064(3) 0.27448(15) 0.0685(7) Uani 1 1 d . . . H5 H 0.5460 0.1313 0.2363 0.082 Uiso 1 1 calc R . . C18 C 0.6942(2) 0.5587(4) -0.26213(14) 0.0786(8) Uani 1 1 d . . . H9 H 0.6495 0.5334 -0.3148 0.094 Uiso 1 1 calc R . . C16 C 0.86531(19) 0.6401(3) -0.18167(13) 0.0569(5) Uani 1 1 d . . . C19 C 0.6520(2) 0.5496(3) -0.18723(14) 0.0655(6) Uani 1 1 d . . . H10 H 0.5794 0.5196 -0.1899 0.079 Uiso 1 1 calc R . . C3 C 0.6553(3) 0.4276(3) 0.38820(16) 0.0818(9) Uani 1 1 d . . . H2 H 0.6826 0.5028 0.4265 0.098 Uiso 1 1 calc R . . C5 C 0.5356(3) 0.2254(3) 0.35020(19) 0.0853(9) Uani 1 1 d . . . H4 H 0.4826 0.1614 0.3632 0.102 Uiso 1 1 calc R . . C4 C 0.5747(3) 0.3360(3) 0.40493(16) 0.0830(9) Uani 1 1 d . . . H3 H 0.5465 0.3500 0.4543 0.100 Uiso 1 1 calc R . . C12 C 0.59585(18) 0.8184(2) -0.04093(12) 0.0501(5) Uani 1 1 d . . . Cl1 Cl 1.00054(6) 0.69811(14) -0.17566(4) 0.1093(4) Uani 1 1 d . . . N2 N 0.52826(17) 0.76345(19) 0.11470(11) 0.0583(5) Uani 1 1 d . . . H6A H 0.5090 0.7487 0.1630 0.070 Uiso 1 1 calc R . . H6B H 0.5100 0.8439 0.0868 0.070 Uiso 1 1 calc R . . C9 C 0.7623(2) 0.3240(2) -0.00738(13) 0.0529(5) Uani 1 1 d . . . N4 N 0.5747(2) 0.9302(2) -0.07139(12) 0.0694(6) Uani 1 1 d . . . N3 N 0.8086(2) 0.2295(2) -0.03082(13) 0.0764(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0929(5) 0.0433(3) 0.0654(4) 0.0163(2) 0.0495(4) 0.0181(2) N1 0.0528(9) 0.0425(8) 0.0444(8) 0.0070(6) 0.0275(7) 0.0060(7) C7 0.0520(11) 0.0382(8) 0.0455(9) 0.0055(7) 0.0258(8) 0.0018(7) C10 0.0448(10) 0.0419(9) 0.0376(8) -0.0001(7) 0.0192(8) 0.0010(7) C11 0.0512(11) 0.0408(9) 0.0376(9) 0.0039(7) 0.0205(8) 0.0056(8) C8 0.0533(11) 0.0398(8) 0.0436(9) 0.0020(7) 0.0263(8) 0.0040(8) C1 0.0656(13) 0.0418(9) 0.0450(10) 0.0114(8) 0.0253(9) 0.0073(9) C13 0.0479(10) 0.0434(9) 0.0399(9) 0.0027(7) 0.0203(8) 0.0058(8) C14 0.0528(11) 0.0399(8) 0.0369(8) 0.0033(7) 0.0223(8) 0.0049(7) C15 0.0594(13) 0.0828(14) 0.0346(9) -0.0054(9) 0.0207(9) -0.0144(11) C17 0.0676(14) 0.0881(15) 0.0360(9) 0.0037(10) 0.0270(10) 0.0002(12) C2 0.0886(18) 0.0461(11) 0.0728(15) 0.0023(10) 0.0250(13) -0.0055(11) C6 0.0913(19) 0.0681(13) 0.0530(12) 0.0027(10) 0.0311(13) -0.0163(13) C18 0.0709(16) 0.132(2) 0.0347(10) -0.0062(12) 0.0142(10) -0.0183(16) C16 0.0564(12) 0.0763(14) 0.0445(10) 0.0007(9) 0.0253(9) -0.0102(10) C19 0.0556(13) 0.0993(17) 0.0445(11) 0.0015(11) 0.0172(10) -0.0108(12) C3 0.136(3) 0.0562(13) 0.0542(13) -0.0049(10) 0.0235(15) 0.0114(15) C5 0.107(2) 0.0930(19) 0.0687(16) 0.0165(14) 0.0482(16) -0.0144(17) C4 0.132(3) 0.0791(16) 0.0481(13) 0.0163(12) 0.0424(15) 0.0270(17) C12 0.0667(13) 0.0501(10) 0.0394(9) 0.0044(8) 0.0250(9) 0.0110(9) Cl1 0.0720(5) 0.2031(10) 0.0601(4) 0.0017(5) 0.0305(4) -0.0507(5) N2 0.0781(13) 0.0563(10) 0.0517(10) 0.0123(7) 0.0393(10) 0.0259(9) C9 0.0724(14) 0.0495(10) 0.0444(10) 0.0050(8) 0.0298(10) 0.0129(10) N4 0.1033(17) 0.0565(10) 0.0555(11) 0.0153(8) 0.0329(11) 0.0260(10) N3 0.1139(19) 0.0675(12) 0.0598(12) 0.0060(9) 0.0455(12) 0.0335(12) _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 C7 1.7616(18) . ? S1 C1 1.7707(19) . ? N1 C7 1.316(2) . ? N1 C13 1.346(2) . ? C7 C8 1.414(2) . ? C10 C8 1.390(2) . ? C10 C11 1.393(2) . ? C10 C14 1.498(2) . ? C11 C13 1.418(2) . ? C11 C12 1.430(3) . ? C8 C9 1.439(2) . ? C1 C2 1.372(3) . ? C1 C6 1.377(3) . ? C13 N2 1.336(2) . ? C14 C15 1.369(3) . ? C14 C19 1.373(3) . ? C15 C16 1.391(2) . ? C17 C16 1.360(3) . ? C17 C18 1.368(3) . ? C2 C3 1.373(4) . ? C6 C5 1.392(3) . ? C18 C19 1.397(3) . ? C16 Cl1 1.735(2) . ? C3 C4 1.365(4) . ? C5 C4 1.350(4) . ? C12 N4 1.132(3) . ? C9 N3 1.136(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 C7 S1 C1 104.47(8) . . ? C7 N1 C13 118.31(14) . . ? N1 C7 C8 123.65(15) . . ? N1 C7 S1 120.06(12) . . ? C8 C7 S1 116.28(13) . . ? C8 C10 C11 118.02(14) . . ? C8 C10 C14 119.88(14) . . ? C11 C10 C14 122.06(15) . . ? C10 C11 C13 119.24(15) . . ? C10 C11 C12 121.89(15) . . ? C13 C11 C12 118.81(15) . . ? C10 C8 C7 118.71(15) . . ? C10 C8 C9 120.22(15) . . ? C7 C8 C9 121.08(15) . . ? C2 C1 C6 119.99(19) . . ? C2 C1 S1 120.99(17) . . ? C6 C1 S1 118.93(17) . . ? N2 C13 N1 116.22(15) . . ? N2 C13 C11 121.71(16) . . ? N1 C13 C11 122.06(15) . . ? C15 C14 C19 120.09(17) . . ? C15 C14 C10 118.98(17) . . ? C19 C14 C10 120.85(17) . . ? C14 C15 C16 119.59(19) . . ? C16 C17 C18 118.98(18) . . ? C1 C2 C3 120.0(2) . . ? C1 C6 C5 118.9(2) . . ? C17 C18 C19 120.9(2) . . ? C17 C16 C15 121.16(19) . . ? C17 C16 Cl1 120.08(15) . . ? C15 C16 Cl1 118.75(17) . . ? C14 C19 C18 119.3(2) . . ? C4 C3 C2 120.1(2) . . ? C4 C5 C6 120.5(3) . . ? C5 C4 C3 120.4(2) . . ? N4 C12 C11 175.49(19) . . ? N3 C9 C8 179.6(3) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.576 _refine_diff_density_min -0.726 _refine_diff_density_rms 0.077