# 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_d469 _database_code_depnum_ccdc_archive 'CCDC 901387' #TrackingRef '13951_web_deposit_cif_file_0_DAVITJISHKARIANI_1347555807.D469.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common D469 _chemical_melting_point ? _chemical_formula_moiety 'C18 H19 N3 S' _chemical_formula_sum 'C18 H19 N3 S' _chemical_formula_weight 309.42 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' S S 0.3331 0.5567 '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 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.86514(13) _cell_length_b 14.6361(3) _cell_length_c 18.7566(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.0394(18) _cell_angle_gamma 90.00 _cell_volume 1606.12(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(1) _cell_measurement_reflns_used 4832 _cell_measurement_theta_min 3.0168 _cell_measurement_theta_max 73.7333 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 1.773 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.62856 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; 'Mon Jul 30 16:40:32 2012' ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(1) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.6501 _diffrn_reflns_number 10315 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 67.46 _reflns_number_total 2883 _reflns_number_gt 2446 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; 'Mon Jul 30 16:40:32 2012' ; _computing_cell_refinement ; 'Mon Jul 30 16:40:32 2012' ; _computing_data_reduction ; 'Mon Jul 30 16:40:32 2012' ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0480P)^2^+0.6550P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2883 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0865 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 -0.0317(2) 0.85784(9) 0.29438(7) 0.0203(3) Uani 1 1 d . . . C2 C 0.1103(3) 0.81466(10) 0.34651(8) 0.0214(3) Uani 1 1 d . . . S2 S 0.08430(8) 0.80657(3) 0.43433(2) 0.02832(14) Uani 1 1 d . . . N3 N 0.2790(2) 0.77503(9) 0.31040(7) 0.0209(3) Uani 1 1 d . . . C4 C 0.3720(3) 0.76616(11) 0.18065(8) 0.0231(4) Uani 1 1 d . . . H4A H 0.5046 0.7314 0.1875 0.028 Uiso 1 1 calc R . . C5 C 0.2912(3) 0.79587(11) 0.11318(9) 0.0246(4) Uani 1 1 d . . . H5A H 0.3717 0.7806 0.0739 0.030 Uiso 1 1 calc R . . C6 C 0.0932(3) 0.84788(11) 0.10281(8) 0.0246(4) Uani 1 1 d . . . H6A H 0.0445 0.8663 0.0568 0.030 Uiso 1 1 calc R . . C7 C -0.0341(3) 0.87311(11) 0.15962(8) 0.0232(4) Uani 1 1 d . . . H7A H -0.1662 0.9081 0.1529 0.028 Uiso 1 1 calc R . . C8 C 0.0476(3) 0.84304(10) 0.22678(8) 0.0198(3) Uani 1 1 d . . . C9 C 0.2448(3) 0.79094(10) 0.23725(8) 0.0200(3) Uani 1 1 d . . . C10 C 0.4627(3) 0.71937(11) 0.34413(9) 0.0234(4) Uani 1 1 d . . . H10A H 0.5044 0.7431 0.3916 0.028 Uiso 1 1 calc R . . H10B H 0.5958 0.7237 0.3164 0.028 Uiso 1 1 calc R . . C11 C 0.3935(3) 0.61947(11) 0.34994(9) 0.0257(4) Uani 1 1 d . . . H11A H 0.2640 0.6150 0.3792 0.031 Uiso 1 1 calc R . . H11B H 0.3460 0.5965 0.3027 0.031 Uiso 1 1 calc R . . C12 C 0.5879(3) 0.56046(12) 0.38251(10) 0.0317(4) Uani 1 1 d . . . H12A H 0.5389 0.4972 0.3817 0.038 Uiso 1 1 calc R . . H12B H 0.7171 0.5653 0.3531 0.038 Uiso 1 1 calc R . . C13 C 0.6653(4) 0.58666(13) 0.45894(11) 0.0446(5) Uani 1 1 d . . . H13A H 0.7876 0.5471 0.4763 0.067 Uiso 1 1 calc R . . H13B H 0.5395 0.5806 0.4887 0.067 Uiso 1 1 calc R . . H13C H 0.7177 0.6488 0.4601 0.067 Uiso 1 1 calc R . . N2 N -0.2307(2) 0.90894(9) 0.29860(7) 0.0218(3) Uani 1 1 d . . . C14 C -0.2561(3) 0.95293(11) 0.35664(8) 0.0224(3) Uani 1 1 d . . . H14A H -0.1469 0.9484 0.3949 0.027 Uiso 1 1 calc R . . C15 C -0.4584(3) 1.01023(10) 0.36212(8) 0.0223(4) Uani 1 1 d . . . C16 C -0.6298(3) 1.01697(11) 0.30652(9) 0.0252(4) Uani 1 1 d . . . H16A H -0.6179 0.9838 0.2647 0.030 Uiso 1 1 calc R . . C17 C -0.8164(3) 1.07284(12) 0.31377(11) 0.0318(4) Uani 1 1 d . . . H17A H -0.9285 1.0779 0.2764 0.038 Uiso 1 1 calc R . . C18 C -0.8377(3) 1.12156(12) 0.37664(11) 0.0356(5) Uani 1 1 d . . . H18A H -0.9651 1.1582 0.3816 0.043 Uiso 1 1 calc R . . C19 C -0.6697(3) 1.11537(12) 0.43156(10) 0.0333(4) Uani 1 1 d . . . H19A H -0.6840 1.1479 0.4736 0.040 Uiso 1 1 calc R . . C20 C -0.4792(3) 1.06074(11) 0.42449(9) 0.0276(4) Uani 1 1 d . . . H20A H -0.3650 1.0578 0.4614 0.033 Uiso 1 1 calc R . . 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 N1 0.0209(7) 0.0210(7) 0.0191(6) 0.0000(5) 0.0028(5) 0.0026(5) C2 0.0231(9) 0.0187(8) 0.0222(8) 0.0008(6) 0.0005(6) -0.0004(6) S2 0.0349(3) 0.0315(2) 0.0189(2) 0.00303(15) 0.00411(17) 0.00585(18) N3 0.0219(7) 0.0207(7) 0.0198(7) 0.0011(5) 0.0008(5) 0.0027(5) C4 0.0230(9) 0.0200(8) 0.0268(8) -0.0018(6) 0.0039(7) 0.0006(7) C5 0.0297(10) 0.0221(8) 0.0228(8) -0.0028(6) 0.0077(7) -0.0034(7) C6 0.0310(9) 0.0226(8) 0.0199(8) 0.0007(6) -0.0007(7) -0.0028(7) C7 0.0248(9) 0.0203(8) 0.0242(8) 0.0008(6) -0.0011(7) 0.0012(7) C8 0.0202(8) 0.0170(7) 0.0222(8) -0.0015(6) 0.0024(6) -0.0014(6) C9 0.0225(9) 0.0169(7) 0.0203(8) 0.0007(6) 0.0006(6) -0.0021(6) C10 0.0218(9) 0.0236(8) 0.0244(8) 0.0020(6) -0.0016(7) 0.0028(7) C11 0.0268(9) 0.0222(8) 0.0275(8) -0.0014(7) -0.0028(7) 0.0019(7) C12 0.0338(10) 0.0225(8) 0.0373(10) 0.0018(7) -0.0081(8) 0.0030(8) C13 0.0625(14) 0.0275(10) 0.0400(11) 0.0057(8) -0.0225(10) -0.0002(10) N2 0.0199(7) 0.0201(6) 0.0257(7) 0.0011(5) 0.0039(6) 0.0025(5) C14 0.0239(9) 0.0204(8) 0.0231(8) 0.0025(6) 0.0031(7) -0.0012(7) C15 0.0245(9) 0.0176(7) 0.0257(8) 0.0029(6) 0.0085(7) -0.0019(7) C16 0.0237(9) 0.0198(8) 0.0326(9) 0.0004(7) 0.0055(7) -0.0029(7) C17 0.0226(9) 0.0246(9) 0.0484(11) 0.0047(8) 0.0045(8) -0.0014(7) C18 0.0288(10) 0.0205(8) 0.0600(12) 0.0029(8) 0.0207(9) 0.0027(7) C19 0.0418(12) 0.0222(8) 0.0386(10) -0.0018(7) 0.0218(9) -0.0002(8) C20 0.0357(10) 0.0225(8) 0.0259(9) 0.0027(7) 0.0108(7) -0.0011(7) _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 C2 1.391(2) . ? N1 N2 1.3929(18) . ? N1 C8 1.3979(19) . ? C2 N3 1.367(2) . ? C2 S2 1.6692(16) . ? N3 C9 1.3922(19) . ? N3 C10 1.459(2) . ? C4 C9 1.388(2) . ? C4 C5 1.389(2) . ? C5 C6 1.391(2) . ? C6 C7 1.393(2) . ? C7 C8 1.387(2) . ? C8 C9 1.388(2) . ? C10 C11 1.523(2) . ? C11 C12 1.523(2) . ? C12 C13 1.522(2) . ? N2 C14 1.283(2) . ? C14 C15 1.463(2) . ? C15 C20 1.397(2) . ? C15 C16 1.400(2) . ? C16 C17 1.381(2) . ? C17 C18 1.391(3) . ? C18 C19 1.377(3) . ? C19 C20 1.388(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 C2 N1 N2 131.81(13) . . ? C2 N1 C8 110.26(13) . . ? N2 N1 C8 117.92(12) . . ? N3 C2 N1 105.25(13) . . ? N3 C2 S2 125.33(12) . . ? N1 C2 S2 129.37(12) . . ? C2 N3 C9 111.00(13) . . ? C2 N3 C10 124.08(13) . . ? C9 N3 C10 124.84(13) . . ? C9 C4 C5 116.59(15) . . ? C4 C5 C6 121.78(15) . . ? C5 C6 C7 121.68(15) . . ? C8 C7 C6 116.17(15) . . ? C7 C8 C9 122.27(15) . . ? C7 C8 N1 131.20(15) . . ? C9 C8 N1 106.50(13) . . ? C8 C9 C4 121.52(15) . . ? C8 C9 N3 106.98(13) . . ? C4 C9 N3 131.48(15) . . ? N3 C10 C11 112.01(14) . . ? C12 C11 C10 112.17(14) . . ? C13 C12 C11 113.59(15) . . ? C14 N2 N1 117.76(13) . . ? N2 C14 C15 119.40(15) . . ? C20 C15 C16 119.10(16) . . ? C20 C15 C14 118.79(16) . . ? C16 C15 C14 122.11(15) . . ? C17 C16 C15 120.07(16) . . ? C16 C17 C18 120.40(18) . . ? C19 C18 C17 119.88(17) . . ? C18 C19 C20 120.30(17) . . ? C19 C20 C15 120.23(17) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 67.46 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.206 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.043