# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_1 #============================================================================ # data_AB167 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H23 N2 O S3' _chemical_formula_weight 403.58 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 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 10.4111(3) _cell_length_b 11.3929(4) _cell_length_c 19.3963(6) _cell_angle_alpha 90.00 _cell_angle_beta 109.976(2) _cell_angle_gamma 90.00 _cell_volume 2162.23(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3902 _cell_measurement_theta_min 4.58 _cell_measurement_theta_max 71.15 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.251 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_max 0.451 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 3.214 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3251 _exptl_absorpt_correction_T_max 0.4993 _exptl_absorpt_process_details SADABS_Bruker_2009 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 14208 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.58 _diffrn_reflns_theta_max 72.03 _reflns_number_total 4110 _reflns_number_gt 3541 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0655P)^2^+0.5231P] 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 4110 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.1215 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.002 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 0.42648(5) -0.59042(5) -0.09613(3) 0.06568(18) Uani 1 1 d . . . S2 S 0.43460(6) -0.75083(6) 0.02406(3) 0.0765(2) Uani 1 1 d . . . S3 S 0.11454(6) -0.59982(4) -0.22332(3) 0.06427(18) Uani 1 1 d . . . O1 O 0.12850(17) -0.41467(15) -0.07640(10) 0.0775(5) Uani 1 1 d . . . N1 N 0.25680(17) -0.57437(16) -0.02371(9) 0.0599(4) Uani 1 1 d . . . N2 N -0.1145(2) -0.33374(19) -0.06232(11) 0.0733(5) Uani 1 1 d . . . H1N2 H -0.1513 -0.3693 -0.0307 0.088 Uiso 0.50(4) 1 d PR A 1 H2N2 H -0.0396 -0.3674 -0.0611 0.088 Uiso 0.50(4) 1 d PR A 2 C1 C 0.36223(19) -0.63680(19) -0.02794(11) 0.0582(5) Uani 1 1 d . . . C2 C 0.2219(2) -0.48368(19) -0.07118(12) 0.0590(5) Uani 1 1 d . . . C3 C 0.3071(2) -0.47055(18) -0.12109(12) 0.0580(5) Uani 1 1 d . . . H3A H 0.3585 -0.3969 -0.1086 0.070 Uiso 1 1 calc R . . C4 C 0.2154(2) -0.46517(18) -0.20196(11) 0.0577(5) Uani 1 1 d . . . H4A H 0.1509 -0.4006 -0.2064 0.069 Uiso 1 1 calc R . . C5 C 0.2928(2) -0.4373(2) -0.25316(12) 0.0657(5) Uani 1 1 d . . . C6 C 0.3420(3) -0.5217(3) -0.28789(17) 0.0919(8) Uani 1 1 d . . . H6A H 0.3271 -0.6006 -0.2807 0.110 Uiso 1 1 calc R . . C7 C 0.4137(4) -0.4909(4) -0.3336(2) 0.1133(11) Uani 1 1 d . . . H7A H 0.4473 -0.5491 -0.3565 0.136 Uiso 1 1 calc R . . C8 C 0.4353(4) -0.3765(4) -0.3453(2) 0.1116(11) Uani 1 1 d . . . H8A H 0.4801 -0.3561 -0.3777 0.134 Uiso 1 1 calc R . . C9 C 0.3909(4) -0.2913(3) -0.3092(3) 0.1246(14) Uani 1 1 d . . . H9A H 0.4093 -0.2128 -0.3153 0.149 Uiso 1 1 calc R . . C10 C 0.3188(4) -0.3212(3) -0.2638(2) 0.1023(10) Uani 1 1 d . . . H10A H 0.2874 -0.2626 -0.2402 0.123 Uiso 1 1 calc R . . C11 C -0.0333(2) -0.55717(18) -0.29672(11) 0.0551(4) Uani 1 1 d . . . C12 C -0.0842(3) -0.4443(2) -0.31047(16) 0.0926(9) Uani 1 1 d . . . H12A H -0.0385 -0.3829 -0.2805 0.111 Uiso 1 1 calc R . . C13 C -0.2026(4) -0.4224(3) -0.36842(19) 0.1078(12) Uani 1 1 d . . . H13A H -0.2349 -0.3459 -0.3779 0.129 Uiso 1 1 calc R . . C14 C -0.2730(3) -0.5113(3) -0.41196(16) 0.0886(8) Uani 1 1 d . . . H14A H -0.3540 -0.4960 -0.4502 0.106 Uiso 1 1 calc R . . C15 C -0.2240(3) -0.6221(3) -0.39910(17) 0.0883(8) Uani 1 1 d . . . H15A H -0.2711 -0.6830 -0.4290 0.106 Uiso 1 1 calc R . . C16 C -0.1050(2) -0.6455(2) -0.34208(15) 0.0744(6) Uani 1 1 d . . . H16A H -0.0724 -0.7221 -0.3341 0.089 Uiso 1 1 calc R . . C17 C -0.2388(5) -0.4705(4) -0.1591(2) 0.1287(14) Uani 1 1 d . . . H17A H -0.3055 -0.4768 -0.2074 0.193 Uiso 1 1 calc R . . H17B H -0.2718 -0.5097 -0.1246 0.193 Uiso 1 1 calc R . . H17C H -0.1549 -0.5062 -0.1584 0.193 Uiso 1 1 calc R . . C18 C -0.2143(3) -0.3441(3) -0.13859(16) 0.0975(9) Uani 1 1 d . . . H18A H -0.2998 -0.3068 -0.1415 0.117 Uiso 1 1 calc R . . H18B H -0.1787 -0.3046 -0.1725 0.117 Uiso 1 1 calc R . . C19 C -0.0820(4) -0.2110(3) -0.0358(2) 0.1086(11) Uani 1 1 d . . . H19A H -0.1632 -0.1734 -0.0324 0.130 Uiso 1 1 calc R . . H19C H -0.0517 -0.1669 -0.0702 0.130 Uiso 1 1 calc R . . C20 C 0.0287(5) -0.2118(5) 0.0385(3) 0.159(2) Uani 1 1 d . . . H20D H 0.0468 -0.1328 0.0565 0.238 Uiso 1 1 calc R . . H20A H 0.1104 -0.2453 0.0344 0.238 Uiso 1 1 calc R . . H20B H -0.0005 -0.2577 0.0719 0.238 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 S1 0.0475(3) 0.0771(4) 0.0704(3) -0.0028(2) 0.0174(2) 0.0072(2) S2 0.0616(3) 0.0726(4) 0.0767(4) 0.0070(3) -0.0003(3) 0.0101(3) S3 0.0621(3) 0.0506(3) 0.0687(3) 0.0075(2) 0.0076(2) -0.0077(2) O1 0.0706(10) 0.0688(10) 0.0992(12) 0.0081(8) 0.0367(9) 0.0189(8) N1 0.0510(9) 0.0666(10) 0.0581(9) 0.0005(8) 0.0133(7) 0.0035(7) N2 0.0671(11) 0.0749(12) 0.0802(12) 0.0094(10) 0.0281(10) 0.0091(9) C1 0.0436(9) 0.0631(11) 0.0572(10) -0.0073(9) 0.0033(8) -0.0033(8) C2 0.0515(10) 0.0583(11) 0.0649(11) -0.0046(9) 0.0168(9) 0.0008(9) C3 0.0497(10) 0.0550(11) 0.0674(12) -0.0035(9) 0.0175(9) -0.0045(8) C4 0.0540(10) 0.0489(10) 0.0662(11) 0.0016(8) 0.0152(9) -0.0053(8) C5 0.0610(12) 0.0661(13) 0.0674(12) 0.0065(10) 0.0185(10) -0.0066(10) C6 0.109(2) 0.0806(17) 0.0995(19) -0.0186(15) 0.0532(18) -0.0224(16) C7 0.127(3) 0.125(3) 0.108(2) -0.026(2) 0.067(2) -0.023(2) C8 0.113(3) 0.126(3) 0.116(3) 0.023(2) 0.065(2) -0.010(2) C9 0.140(3) 0.094(2) 0.174(4) 0.043(2) 0.098(3) 0.005(2) C10 0.119(2) 0.0701(17) 0.144(3) 0.0216(17) 0.079(2) 0.0044(16) C11 0.0522(10) 0.0557(11) 0.0572(10) 0.0027(8) 0.0185(8) -0.0040(8) C12 0.0957(19) 0.0603(14) 0.0862(17) -0.0087(12) -0.0151(15) 0.0063(13) C13 0.103(2) 0.0692(16) 0.109(2) 0.0014(15) -0.0172(18) 0.0141(15) C14 0.0633(14) 0.0922(19) 0.0879(17) 0.0061(15) -0.0030(12) -0.0021(13) C15 0.0614(14) 0.0776(16) 0.108(2) -0.0146(15) 0.0060(13) -0.0184(12) C16 0.0544(11) 0.0566(12) 0.1029(17) -0.0033(12) 0.0151(12) -0.0097(10) C17 0.138(3) 0.145(4) 0.094(2) -0.014(2) 0.029(2) -0.042(3) C18 0.0844(18) 0.125(3) 0.0817(17) 0.0284(18) 0.0270(14) 0.0150(17) C19 0.112(2) 0.0805(19) 0.151(3) -0.005(2) 0.069(2) -0.0057(18) C20 0.141(4) 0.174(5) 0.161(4) -0.072(4) 0.052(3) -0.046(4) _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 C1 1.755(2) . ? S1 C3 1.798(2) . ? S2 C1 1.659(2) . ? S3 C11 1.770(2) . ? S3 C4 1.825(2) . ? O1 C2 1.227(3) . ? N1 C1 1.334(3) . ? N1 C2 1.349(3) . ? N2 C19 1.488(4) . ? N2 C18 1.494(4) . ? N2 H1N2 0.9211 . ? N2 H2N2 0.8618 . ? C2 C3 1.527(3) . ? C3 C4 1.534(3) . ? C3 H3A 0.9800 . ? C4 C5 1.511(3) . ? C4 H4A 0.9800 . ? C5 C6 1.370(4) . ? C5 C10 1.380(4) . ? C6 C7 1.386(4) . ? C6 H6A 0.9300 . ? C7 C8 1.355(5) . ? C7 H7A 0.9300 . ? C8 C9 1.366(5) . ? C8 H8A 0.9300 . ? C9 C10 1.381(4) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C16 1.377(3) . ? C11 C12 1.382(3) . ? C12 C13 1.378(4) . ? C12 H12A 0.9300 . ? C13 C14 1.361(4) . ? C13 H13A 0.9300 . ? C14 C15 1.352(4) . ? C14 H14A 0.9300 . ? C15 C16 1.376(4) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 C18 1.492(6) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.507(6) . ? C19 H19A 0.9700 . ? C19 H19C 0.9700 . ? C20 H20D 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? 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 C1 S1 C3 91.43(10) . . ? C11 S3 C4 103.09(9) . . ? C1 N1 C2 113.71(18) . . ? C19 N2 C18 114.6(3) . . ? C19 N2 H1N2 106.3 . . ? C18 N2 H1N2 108.5 . . ? C19 N2 H2N2 108.2 . . ? C18 N2 H2N2 108.0 . . ? H1N2 N2 H2N2 111.3 . . ? N1 C1 S2 126.33(17) . . ? N1 C1 S1 114.79(16) . . ? S2 C1 S1 118.88(12) . . ? O1 C2 N1 124.6(2) . . ? O1 C2 C3 120.0(2) . . ? N1 C2 C3 115.37(18) . . ? C2 C3 C4 111.04(16) . . ? C2 C3 S1 104.64(14) . . ? C4 C3 S1 115.92(15) . . ? C2 C3 H3A 108.3 . . ? C4 C3 H3A 108.3 . . ? S1 C3 H3A 108.3 . . ? C5 C4 C3 113.28(17) . . ? C5 C4 S3 114.95(16) . . ? C3 C4 S3 107.90(14) . . ? C5 C4 H4A 106.7 . . ? C3 C4 H4A 106.7 . . ? S3 C4 H4A 106.7 . . ? C6 C5 C10 118.3(2) . . ? C6 C5 C4 123.3(2) . . ? C10 C5 C4 118.4(2) . . ? C5 C6 C7 120.7(3) . . ? C5 C6 H6A 119.7 . . ? C7 C6 H6A 119.7 . . ? C8 C7 C6 120.5(3) . . ? C8 C7 H7A 119.7 . . ? C6 C7 H7A 119.7 . . ? C7 C8 C9 119.6(3) . . ? C7 C8 H8A 120.2 . . ? C9 C8 H8A 120.2 . . ? C8 C9 C10 120.2(3) . . ? C8 C9 H9A 119.9 . . ? C10 C9 H9A 119.9 . . ? C5 C10 C9 120.7(3) . . ? C5 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C16 C11 C12 117.9(2) . . ? C16 C11 S3 116.49(17) . . ? C12 C11 S3 125.56(17) . . ? C13 C12 C11 120.2(2) . . ? C13 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C14 C13 C12 120.9(3) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C15 C14 C13 119.4(3) . . ? C15 C14 H14A 120.3 . . ? C13 C14 H14A 120.3 . . ? C14 C15 C16 120.5(2) . . ? C14 C15 H15A 119.7 . . ? C16 C15 H15A 119.7 . . ? C15 C16 C11 121.0(2) . . ? C15 C16 H16A 119.5 . . ? C11 C16 H16A 119.5 . . ? C18 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C18 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C17 C18 N2 109.8(3) . . ? C17 C18 H18A 109.7 . . ? N2 C18 H18A 109.7 . . ? C17 C18 H18B 109.7 . . ? N2 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? N2 C19 C20 109.5(3) . . ? N2 C19 H19A 109.8 . . ? C20 C19 H19A 109.8 . . ? N2 C19 H19C 109.8 . . ? C20 C19 H19C 109.8 . . ? H19A C19 H19C 108.2 . . ? C19 C20 H20D 109.5 . . ? C19 C20 H20A 109.5 . . ? H20D C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20D C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? 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 C2 N1 C1 S2 177.83(16) . . . . ? C2 N1 C1 S1 -2.3(2) . . . . ? C3 S1 C1 N1 2.44(16) . . . . ? C3 S1 C1 S2 -177.70(13) . . . . ? C1 N1 C2 O1 -179.7(2) . . . . ? C1 N1 C2 C3 0.9(3) . . . . ? O1 C2 C3 C4 -52.8(3) . . . . ? N1 C2 C3 C4 126.65(19) . . . . ? O1 C2 C3 S1 -178.61(18) . . . . ? N1 C2 C3 S1 0.9(2) . . . . ? C1 S1 C3 C2 -1.72(14) . . . . ? C1 S1 C3 C4 -124.37(15) . . . . ? C2 C3 C4 C5 172.94(18) . . . . ? S1 C3 C4 C5 -67.9(2) . . . . ? C2 C3 C4 S3 -58.63(19) . . . . ? S1 C3 C4 S3 60.57(18) . . . . ? C11 S3 C4 C5 -78.95(17) . . . . ? C11 S3 C4 C3 153.59(14) . . . . ? C3 C4 C5 C6 93.8(3) . . . . ? S3 C4 C5 C6 -30.9(3) . . . . ? C3 C4 C5 C10 -84.2(3) . . . . ? S3 C4 C5 C10 151.1(2) . . . . ? C10 C5 C6 C7 -1.2(5) . . . . ? C4 C5 C6 C7 -179.2(3) . . . . ? C5 C6 C7 C8 -0.6(6) . . . . ? C6 C7 C8 C9 2.8(6) . . . . ? C7 C8 C9 C10 -3.1(7) . . . . ? C6 C5 C10 C9 0.9(5) . . . . ? C4 C5 C10 C9 179.0(3) . . . . ? C8 C9 C10 C5 1.2(6) . . . . ? C4 S3 C11 C16 157.06(18) . . . . ? C4 S3 C11 C12 -25.2(3) . . . . ? C16 C11 C12 C13 -0.6(5) . . . . ? S3 C11 C12 C13 -178.3(3) . . . . ? C11 C12 C13 C14 1.5(6) . . . . ? C12 C13 C14 C15 -1.6(6) . . . . ? C13 C14 C15 C16 0.7(5) . . . . ? C14 C15 C16 C11 0.2(4) . . . . ? C12 C11 C16 C15 -0.3(4) . . . . ? S3 C11 C16 C15 177.6(2) . . . . ? C19 N2 C18 C17 180.0(3) . . . . ? C18 N2 C19 C20 -174.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 72.03 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.308 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 930797' ####################################################################### # # 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_1 #============================================================================ # data_AB180 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 N2 O S2' _chemical_formula_weight 294.42 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 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 10.7960(3) _cell_length_b 13.0807(4) _cell_length_c 14.6416(4) _cell_angle_alpha 90.00 _cell_angle_beta 126.696(2) _cell_angle_gamma 90.00 _cell_volume 1657.90(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2969 _cell_measurement_theta_min 4.16 _cell_measurement_theta_max 69.73 _exptl_crystal_description Block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 2.862 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3363 _exptl_absorpt_correction_T_max 0.4898 _exptl_absorpt_process_details SADABS_Bruker_2009 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 10343 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.06 _diffrn_reflns_theta_max 65.00 _reflns_number_total 2726 _reflns_number_gt 2247 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1170P)^2^+0.5835P] 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 SHELXL _refine_ls_extinction_coef 0.0062(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2726 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0633 _refine_ls_wR_factor_ref 0.2091 _refine_ls_wR_factor_gt 0.1992 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 0.21928(9) -0.65046(6) -0.00505(7) 0.0756(4) Uani 1 1 d . . . S2 S -0.01504(13) -0.81115(9) -0.13375(14) 0.1292(6) Uani 1 1 d . . . O1 O 0.5477(3) -0.8217(2) 0.0618(3) 0.1070(10) Uani 1 1 d . . . N1 N 0.2866(3) -0.8322(2) -0.0354(3) 0.0821(8) Uani 1 1 d . . . C1 C 0.6887(5) -0.4602(3) 0.2070(4) 0.1060(14) Uani 1 1 d . . . H1A H 0.7742 -0.4968 0.2245 0.127 Uiso 1 1 calc R . . C2 C 0.7080(6) -0.3596(4) 0.2438(5) 0.1210(17) Uani 1 1 d . . . H2A H 0.8056 -0.3300 0.2850 0.145 Uiso 1 1 calc R . . C3 C 0.5873(6) -0.3044(3) 0.2207(4) 0.1015(13) Uani 1 1 d . . . H3A H 0.6009 -0.2376 0.2468 0.122 Uiso 1 1 calc R . . C4 C 0.4479(6) -0.3474(3) 0.1598(5) 0.1134(15) Uani 1 1 d . . . H4A H 0.3641 -0.3096 0.1440 0.136 Uiso 1 1 calc R . . C5 C 0.4238(5) -0.4465(3) 0.1192(4) 0.0976(12) Uani 1 1 d . . . H5A H 0.3242 -0.4730 0.0738 0.117 Uiso 1 1 calc R . . C6 C 0.5472(4) -0.5067(3) 0.1457(3) 0.0733(8) Uani 1 1 d . . . C7 C 0.5345(4) -0.6124(3) 0.1118(3) 0.0744(8) Uani 1 1 d . . . H7A H 0.6271 -0.6423 0.1344 0.089 Uiso 1 1 calc R . . C8 C 0.4112(4) -0.6744(2) 0.0531(3) 0.0670(8) Uani 1 1 d . . . C9 C 0.4241(4) -0.7824(2) 0.0275(3) 0.0753(8) Uani 1 1 d . . . C10 C 0.1681(4) -0.7764(3) -0.0600(3) 0.0816(9) Uani 1 1 d . . . N2 N -0.2348(3) -0.5361(2) -0.3902(3) 0.0871(9) Uani 1 1 d . . . H1N2 H -0.3280 -0.5667 -0.4176 0.105 Uiso 1 1 d R . . H2N2 H -0.2632 -0.4651 -0.4105 0.105 Uiso 1 1 d R . . C11 C -0.1731(10) -0.4846(7) -0.2138(6) 0.173(3) Uani 1 1 d . . . H11A H -0.1496 -0.5235 -0.1496 0.260 Uiso 1 1 calc R . . H11B H -0.2827 -0.4748 -0.2663 0.260 Uiso 1 1 calc R . . H11C H -0.1227 -0.4193 -0.1882 0.260 Uiso 1 1 calc R . . C12 C -0.1188(6) -0.5395(4) -0.2701(4) 0.1230(17) Uani 1 1 d . . . H12A H -0.0244 -0.5084 -0.2510 0.148 Uiso 1 1 calc R . . H12B H -0.0966 -0.6100 -0.2444 0.148 Uiso 1 1 calc R . . C13 C -0.1797(6) -0.5881(4) -0.4557(5) 0.1143(15) Uani 1 1 d . . . H13A H -0.0869 -0.5549 -0.4370 0.137 Uiso 1 1 calc R . . H13B H -0.1560 -0.6595 -0.4339 0.137 Uiso 1 1 calc R . . C14 C -0.3046(11) -0.5799(7) -0.5802(7) 0.187(3) Uani 1 1 d . . . H14A H -0.2767 -0.6186 -0.6211 0.280 Uiso 1 1 calc R . . H14B H -0.3186 -0.5095 -0.6029 0.280 Uiso 1 1 calc R . . H14C H -0.3991 -0.6063 -0.5969 0.280 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 S1 0.0624(5) 0.0574(5) 0.0917(6) -0.0019(4) 0.0378(4) 0.0066(3) S2 0.0759(7) 0.0856(8) 0.1752(13) -0.0206(7) 0.0476(8) -0.0139(5) O1 0.0846(17) 0.0784(16) 0.151(3) -0.0123(16) 0.0666(17) 0.0164(14) N1 0.0823(19) 0.0570(14) 0.0960(19) -0.0095(13) 0.0473(16) 0.0000(13) C1 0.071(2) 0.085(3) 0.126(3) -0.012(2) 0.040(2) -0.0064(19) C2 0.096(3) 0.090(3) 0.127(4) -0.017(3) 0.039(3) -0.026(3) C3 0.122(4) 0.067(2) 0.105(3) -0.016(2) 0.062(3) -0.016(2) C4 0.115(3) 0.067(2) 0.166(4) -0.015(3) 0.088(3) 0.000(2) C5 0.083(2) 0.068(2) 0.134(3) -0.016(2) 0.061(2) -0.0070(18) C6 0.0712(18) 0.0676(18) 0.0761(18) -0.0014(15) 0.0412(16) -0.0012(15) C7 0.0649(18) 0.0699(19) 0.085(2) 0.0007(16) 0.0433(16) 0.0057(15) C8 0.0654(17) 0.0575(15) 0.0728(17) 0.0022(13) 0.0384(15) 0.0067(13) C9 0.076(2) 0.0625(17) 0.087(2) -0.0014(15) 0.0486(17) 0.0092(15) C10 0.076(2) 0.0591(18) 0.094(2) -0.0029(16) 0.0421(18) -0.0006(15) N2 0.0648(16) 0.0659(16) 0.103(2) 0.0173(15) 0.0353(15) -0.0050(13) C11 0.214(8) 0.202(7) 0.144(5) 0.036(5) 0.129(6) 0.073(6) C12 0.108(3) 0.115(4) 0.106(3) 0.015(3) 0.042(3) 0.000(3) C13 0.107(3) 0.087(3) 0.160(5) 0.005(3) 0.086(3) 0.001(2) C14 0.258(10) 0.154(6) 0.158(6) -0.010(5) 0.129(7) -0.007(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 S1 C8 1.734(3) . ? S1 C10 1.771(3) . ? S2 C10 1.652(4) . ? O1 C9 1.224(4) . ? N1 C10 1.323(5) . ? N1 C9 1.357(4) . ? C1 C6 1.368(5) . ? C1 C2 1.390(6) . ? C1 H1A 0.9300 . ? C2 C3 1.344(7) . ? C2 H2A 0.9300 . ? C3 C4 1.331(6) . ? C3 H3A 0.9300 . ? C4 C5 1.385(6) . ? C4 H4A 0.9300 . ? C5 C6 1.388(5) . ? C5 H5A 0.9300 . ? C6 C7 1.448(5) . ? C7 C8 1.342(5) . ? C7 H7A 0.9300 . ? C8 C9 1.489(4) . ? N2 C12 1.426(6) . ? N2 C13 1.555(6) . ? N2 H1N2 0.9226 . ? N2 H2N2 0.9677 . ? C11 C12 1.454(8) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.488(10) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 C8 S1 C10 90.71(16) . . ? C10 N1 C9 114.0(3) . . ? C6 C1 C2 121.7(4) . . ? C6 C1 H1A 119.2 . . ? C2 C1 H1A 119.2 . . ? C3 C2 C1 120.8(4) . . ? C3 C2 H2A 119.6 . . ? C1 C2 H2A 119.6 . . ? C4 C3 C2 118.7(4) . . ? C4 C3 H3A 120.7 . . ? C2 C3 H3A 120.7 . . ? C3 C4 C5 122.0(4) . . ? C3 C4 H4A 119.0 . . ? C5 C4 H4A 119.0 . . ? C4 C5 C6 120.6(4) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C1 C6 C5 116.1(3) . . ? C1 C6 C7 119.3(3) . . ? C5 C6 C7 124.6(3) . . ? C8 C7 C6 130.6(3) . . ? C8 C7 H7A 114.7 . . ? C6 C7 H7A 114.7 . . ? C7 C8 C9 121.9(3) . . ? C7 C8 S1 130.0(2) . . ? C9 C8 S1 108.1(2) . . ? O1 C9 N1 123.9(3) . . ? O1 C9 C8 122.6(3) . . ? N1 C9 C8 113.5(3) . . ? N1 C10 S2 127.7(3) . . ? N1 C10 S1 113.7(3) . . ? S2 C10 S1 118.7(2) . . ? C12 N2 C13 111.7(4) . . ? C12 N2 H1N2 116.6 . . ? C13 N2 H1N2 105.2 . . ? C12 N2 H2N2 107.0 . . ? C13 N2 H2N2 113.5 . . ? H1N2 N2 H2N2 102.7 . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 C11 109.3(5) . . ? N2 C12 H12A 109.8 . . ? C11 C12 H12A 109.8 . . ? N2 C12 H12B 109.8 . . ? C11 C12 H12B 109.8 . . ? H12A C12 H12B 108.3 . . ? C14 C13 N2 108.8(5) . . ? C14 C13 H13A 109.9 . . ? N2 C13 H13A 109.9 . . ? C14 C13 H13B 109.9 . . ? N2 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 C6 C1 C2 C3 0.4(8) . . . . ? C1 C2 C3 C4 -1.3(8) . . . . ? C2 C3 C4 C5 -0.4(8) . . . . ? C3 C4 C5 C6 3.1(8) . . . . ? C2 C1 C6 C5 2.1(7) . . . . ? C2 C1 C6 C7 -178.6(4) . . . . ? C4 C5 C6 C1 -3.8(7) . . . . ? C4 C5 C6 C7 177.0(4) . . . . ? C1 C6 C7 C8 179.4(4) . . . . ? C5 C6 C7 C8 -1.4(6) . . . . ? C6 C7 C8 C9 -179.8(3) . . . . ? C6 C7 C8 S1 0.4(6) . . . . ? C10 S1 C8 C7 178.7(3) . . . . ? C10 S1 C8 C9 -1.2(3) . . . . ? C10 N1 C9 O1 177.7(4) . . . . ? C10 N1 C9 C8 -1.3(5) . . . . ? C7 C8 C9 O1 2.8(6) . . . . ? S1 C8 C9 O1 -177.3(3) . . . . ? C7 C8 C9 N1 -178.2(3) . . . . ? S1 C8 C9 N1 1.7(4) . . . . ? C9 N1 C10 S2 -179.7(3) . . . . ? C9 N1 C10 S1 0.3(5) . . . . ? C8 S1 C10 N1 0.6(3) . . . . ? C8 S1 C10 S2 -179.4(3) . . . . ? C13 N2 C12 C11 176.6(5) . . . . ? C12 N2 C13 C14 -178.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 65.00 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.514 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 931815' ####################################################################### # # 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_1 #============================================================================ # data_AB171 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H21 N2 O S2' _chemical_formula_weight 321.47 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 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 7.3038(2) _cell_length_b 13.6420(3) _cell_length_c 17.9671(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.589(2) _cell_angle_gamma 90.00 _cell_volume 1765.20(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1678 _cell_measurement_theta_min 4.99 _cell_measurement_theta_max 68.72 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 2.729 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4572 _exptl_absorpt_correction_T_max 0.5384 _exptl_absorpt_process_details SADABS_Bruker_2009 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12373 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.09 _diffrn_reflns_theta_max 69.84 _reflns_number_total 3300 _reflns_number_gt 2771 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0624P)^2^+0.3604P] 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 3300 _refine_ls_number_parameters 198 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1294 _refine_ls_wR_factor_gt 0.1234 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.32970(8) 0.81658(4) 0.15349(3) 0.06144(19) Uani 1 1 d . . . S2 S 0.35900(10) 0.64925(5) 0.25996(3) 0.0758(2) Uani 1 1 d . . . O1 O 0.0780(3) 0.66519(13) -0.00937(9) 0.0890(6) Uani 1 1 d . . . N1 N 0.2006(3) 0.64208(13) 0.11479(10) 0.0601(4) Uani 1 1 d . . . N2 N -0.0223(2) 0.95851(13) 0.36893(9) 0.0518(4) Uani 1 1 d . . . C1 C 0.2050(3) 1.01395(19) -0.07162(12) 0.0697(6) Uani 1 1 d . . . H1A H 0.1598 0.9772 -0.1143 0.084 Uiso 1 1 calc R . . C2 C 0.2386(4) 1.1123(2) -0.07885(14) 0.0796(7) Uani 1 1 d . . . H2A H 0.2159 1.1414 -0.1263 0.096 Uiso 1 1 calc R . . C3 C 0.3049(4) 1.16751(19) -0.01703(16) 0.0762(7) Uani 1 1 d . . . H3A H 0.3281 1.2340 -0.0223 0.091 Uiso 1 1 calc R . . C4 C 0.3376(4) 1.12452(18) 0.05337(14) 0.0725(6) Uani 1 1 d . . . H4A H 0.3817 1.1622 0.0957 0.087 Uiso 1 1 calc R . . C5 C 0.3053(3) 1.02595(16) 0.06116(12) 0.0638(5) Uani 1 1 d . . . H5A H 0.3289 0.9975 0.1088 0.077 Uiso 1 1 calc R . . C6 C 0.2378(3) 0.96849(16) -0.00115(11) 0.0561(5) Uani 1 1 d . . . C7 C 0.1968(3) 0.86435(16) 0.00255(11) 0.0605(5) Uani 1 1 d . . . H7A H 0.1415 0.8372 -0.0432 0.073 Uiso 1 1 calc R . . C8 C 0.2246(3) 0.80078(15) 0.05993(11) 0.0543(5) Uani 1 1 d . . . C9 C 0.1612(3) 0.69704(16) 0.05062(12) 0.0611(5) Uani 1 1 d . . . C10 C 0.2890(3) 0.69172(15) 0.17353(12) 0.0551(5) Uani 1 1 d . . . C11 C -0.3313(4) 0.8891(2) 0.35045(16) 0.0815(7) Uani 1 1 d . . . H11A H -0.3807 0.9529 0.3576 0.122 Uiso 1 1 calc R . . H11B H -0.3007 0.8567 0.3984 0.122 Uiso 1 1 calc R . . H11C H -0.4222 0.8512 0.3178 0.122 Uiso 1 1 calc R . . C12 C -0.1594(3) 0.89910(15) 0.31526(11) 0.0592(5) Uani 1 1 d . . . H12A H -0.1910 0.9353 0.2677 0.071 Uiso 1 1 calc R . . C13 C -0.0789(4) 0.80101(18) 0.29900(15) 0.0810(7) Uani 1 1 d . . . H13A H 0.0273 0.8109 0.2748 0.121 Uiso 1 1 calc R . . H13B H -0.1707 0.7637 0.2664 0.121 Uiso 1 1 calc R . . H13C H -0.0421 0.7661 0.3455 0.121 Uiso 1 1 calc R . . C14 C 0.2692(4) 1.0424(3) 0.4112(2) 0.1052(11) Uani 1 1 d . . . H14A H 0.3878 1.0602 0.3990 0.158 Uiso 1 1 calc R . . H14B H 0.2870 1.0045 0.4569 0.158 Uiso 1 1 calc R . . H14C H 0.2001 1.1006 0.4182 0.158 Uiso 1 1 calc R . . C15 C 0.1628(3) 0.98198(18) 0.34754(13) 0.0669(6) Uani 1 1 d . . . H15A H 0.2299 0.9204 0.3442 0.080 Uiso 1 1 calc R . . C16 C 0.1415(4) 1.0324(2) 0.27178(17) 0.0939(9) Uani 1 1 d . . . H16A H 0.0778 0.9896 0.2336 0.141 Uiso 1 1 calc R . . H16B H 0.2619 1.0480 0.2603 0.141 Uiso 1 1 calc R . . H16C H 0.0711 1.0916 0.2733 0.141 Uiso 1 1 calc R . . H1N2 H -0.071(3) 1.0059(16) 0.3778(11) 0.044(5) Uiso 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 0.0797(4) 0.0492(3) 0.0516(3) -0.0010(2) -0.0003(2) -0.0165(2) S2 0.0907(4) 0.0651(4) 0.0648(4) 0.0124(3) -0.0073(3) -0.0125(3) O1 0.1298(16) 0.0658(10) 0.0629(10) -0.0124(8) -0.0084(10) -0.0288(10) N1 0.0701(10) 0.0460(10) 0.0619(10) -0.0026(8) 0.0041(8) -0.0097(8) N2 0.0596(9) 0.0399(9) 0.0544(9) -0.0045(7) 0.0051(7) 0.0072(7) C1 0.0851(15) 0.0694(15) 0.0530(11) 0.0055(10) 0.0070(10) 0.0010(12) C2 0.0933(17) 0.0775(17) 0.0677(14) 0.0210(13) 0.0121(12) 0.0117(14) C3 0.0816(15) 0.0551(13) 0.0909(17) 0.0150(12) 0.0117(13) 0.0056(11) C4 0.0851(15) 0.0538(13) 0.0739(14) -0.0010(11) -0.0008(12) 0.0013(11) C5 0.0779(14) 0.0552(12) 0.0557(11) 0.0040(9) 0.0042(10) -0.0024(10) C6 0.0573(10) 0.0578(12) 0.0523(10) 0.0024(9) 0.0067(8) -0.0002(9) C7 0.0677(12) 0.0619(13) 0.0505(10) -0.0058(9) 0.0059(9) -0.0077(10) C8 0.0612(11) 0.0503(11) 0.0505(10) -0.0036(8) 0.0068(8) -0.0076(9) C9 0.0704(13) 0.0539(12) 0.0576(12) -0.0076(9) 0.0063(10) -0.0111(10) C10 0.0551(10) 0.0487(11) 0.0602(11) 0.0003(9) 0.0060(9) -0.0055(8) C11 0.0741(15) 0.0658(16) 0.1028(19) -0.0139(13) 0.0097(14) -0.0111(12) C12 0.0763(13) 0.0465(11) 0.0506(10) -0.0027(8) -0.0020(9) 0.0031(9) C13 0.108(2) 0.0539(14) 0.0773(15) -0.0158(11) 0.0046(14) 0.0098(13) C14 0.0674(16) 0.107(2) 0.139(3) -0.044(2) 0.0119(16) -0.0138(15) C15 0.0589(12) 0.0607(14) 0.0821(15) -0.0038(11) 0.0146(10) 0.0098(10) C16 0.0922(19) 0.092(2) 0.105(2) 0.0244(17) 0.0391(16) 0.0030(16) _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 C8 1.741(2) . ? S1 C10 1.776(2) . ? S2 C10 1.657(2) . ? O1 C9 1.225(2) . ? N1 C10 1.327(3) . ? N1 C9 1.365(3) . ? N2 C15 1.501(3) . ? N2 C12 1.506(3) . ? N2 H1N2 0.77(2) . ? C1 C2 1.374(4) . ? C1 C6 1.394(3) . ? C1 H1A 0.9300 . ? C2 C3 1.362(4) . ? C2 H2A 0.9300 . ? C3 C4 1.379(4) . ? C3 H3A 0.9300 . ? C4 C5 1.376(3) . ? C4 H4A 0.9300 . ? C5 C6 1.388(3) . ? C5 H5A 0.9300 . ? C6 C7 1.456(3) . ? C7 C8 1.337(3) . ? C7 H7A 0.9300 . ? C8 C9 1.490(3) . ? C11 C12 1.503(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.510(3) . ? C12 H12A 0.9800 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.515(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.510(3) . ? C15 H15A 0.9800 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 C8 S1 C10 90.87(9) . . ? C10 N1 C9 113.41(18) . . ? C15 N2 C12 118.83(17) . . ? C15 N2 H1N2 109.8(16) . . ? C12 N2 H1N2 107.9(15) . . ? C2 C1 C6 120.9(2) . . ? C2 C1 H1A 119.5 . . ? C6 C1 H1A 119.5 . . ? C3 C2 C1 120.5(2) . . ? C3 C2 H2A 119.8 . . ? C1 C2 H2A 119.8 . . ? C2 C3 C4 119.8(2) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C5 C4 C3 120.2(2) . . ? C5 C4 H4A 119.9 . . ? C3 C4 H4A 119.9 . . ? C4 C5 C6 120.9(2) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C5 C6 C1 117.7(2) . . ? C5 C6 C7 124.23(19) . . ? C1 C6 C7 118.03(19) . . ? C8 C7 C6 131.49(19) . . ? C8 C7 H7A 114.3 . . ? C6 C7 H7A 114.3 . . ? C7 C8 C9 121.69(18) . . ? C7 C8 S1 130.56(16) . . ? C9 C8 S1 107.75(14) . . ? O1 C9 N1 123.5(2) . . ? O1 C9 C8 122.3(2) . . ? N1 C9 C8 114.14(17) . . ? N1 C10 S2 126.88(16) . . ? N1 C10 S1 113.81(15) . . ? S2 C10 S1 119.31(12) . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C11 C12 N2 107.01(17) . . ? C11 C12 C13 112.4(2) . . ? N2 C12 C13 111.22(19) . . ? C11 C12 H12A 108.7 . . ? N2 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C15 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 C16 111.46(19) . . ? N2 C15 C14 107.03(19) . . ? C16 C15 C14 113.4(3) . . ? N2 C15 H15A 108.3 . . ? C16 C15 H15A 108.3 . . ? C14 C15 H15A 108.3 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 C6 C1 C2 C3 0.0(4) . . . . ? C1 C2 C3 C4 -0.4(4) . . . . ? C2 C3 C4 C5 0.7(4) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C4 C5 C6 C7 -178.8(2) . . . . ? C2 C1 C6 C5 0.0(4) . . . . ? C2 C1 C6 C7 179.2(2) . . . . ? C5 C6 C7 C8 -5.8(4) . . . . ? C1 C6 C7 C8 175.1(2) . . . . ? C6 C7 C8 C9 176.8(2) . . . . ? C6 C7 C8 S1 -2.7(4) . . . . ? C10 S1 C8 C7 -179.8(2) . . . . ? C10 S1 C8 C9 0.71(16) . . . . ? C10 N1 C9 O1 -178.9(2) . . . . ? C10 N1 C9 C8 -0.2(3) . . . . ? C7 C8 C9 O1 -1.3(4) . . . . ? S1 C8 C9 O1 178.3(2) . . . . ? C7 C8 C9 N1 180.0(2) . . . . ? S1 C8 C9 N1 -0.4(2) . . . . ? C9 N1 C10 S2 -179.86(17) . . . . ? C9 N1 C10 S1 0.8(2) . . . . ? C8 S1 C10 N1 -0.91(17) . . . . ? C8 S1 C10 S2 179.71(14) . . . . ? C15 N2 C12 C11 -178.86(19) . . . . ? C15 N2 C12 C13 58.1(3) . . . . ? C12 N2 C15 C16 55.1(3) . . . . ? C12 N2 C15 C14 179.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 69.84 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.514 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 930934' ####################################################################### # # 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_1 #============================================================================ # data_ABH2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Cl N2 O S2' _chemical_formula_weight 327.86 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_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 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 7.3389(2) _cell_length_b 13.0121(3) _cell_length_c 17.6769(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.169(2) _cell_angle_gamma 90.00 _cell_volume 1661.53(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3347 _cell_measurement_theta_min 3.40 _cell_measurement_theta_max 69.71 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 4.357 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2365 _exptl_absorpt_correction_T_max 0.4137 _exptl_absorpt_process_details SADABS_Bruker_2009 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 11035 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.24 _diffrn_reflns_theta_max 70.26 _reflns_number_total 3117 _reflns_number_gt 2588 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0796P)^2^+0.4031P] 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 3117 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1395 _refine_ls_wR_factor_gt 0.1341 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.013 _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 Cl1 Cl 0.08024(11) -0.31694(5) 0.52213(5) 0.0806(3) Uani 1 1 d . . . S1 S 0.22440(9) 0.16423(4) 0.34367(3) 0.0554(2) Uani 1 1 d . . . S2 S 0.23937(13) 0.32974(5) 0.23104(4) 0.0779(3) Uani 1 1 d . . . O1 O 0.4460(3) 0.32744(14) 0.51324(11) 0.0717(5) Uani 1 1 d . . . N2 N 0.4749(4) 0.46045(17) 0.63589(13) 0.0632(6) Uani 1 1 d . . . N1 N 0.3624(3) 0.34526(15) 0.38298(11) 0.0577(5) Uani 1 1 d . . . C1 C 0.2799(4) -0.0370(2) 0.57364(13) 0.0602(6) Uani 1 1 d . . . H1A H 0.3301 -0.0010 0.6179 0.072 Uiso 1 1 calc R . . C2 C 0.2280(4) -0.1377(2) 0.58013(14) 0.0642(6) Uani 1 1 d . . . H2A H 0.2443 -0.1695 0.6279 0.077 Uiso 1 1 calc R . . C3 C 0.1520(4) -0.19046(18) 0.51497(15) 0.0574(6) Uani 1 1 d . . . C4 C 0.1299(4) -0.14524(19) 0.44392(15) 0.0613(6) Uani 1 1 d . . . H4A H 0.0797 -0.1822 0.4001 0.074 Uiso 1 1 calc R . . C5 C 0.1827(4) -0.04472(19) 0.43815(13) 0.0587(6) Uani 1 1 d . . . H5A H 0.1669 -0.0141 0.3899 0.070 Uiso 1 1 calc R . . C6 C 0.2596(3) 0.01289(17) 0.50262(12) 0.0485(5) Uani 1 1 d . . . C7 C 0.3174(3) 0.11897(18) 0.50063(12) 0.0508(5) Uani 1 1 d . . . H7A H 0.3678 0.1467 0.5482 0.061 Uiso 1 1 calc R . . C8 C 0.3099(3) 0.18407(16) 0.44087(12) 0.0479(5) Uani 1 1 d . . . C9 C 0.3788(3) 0.29147(18) 0.45036(13) 0.0529(5) Uani 1 1 d . . . C10 C 0.2835(3) 0.29132(18) 0.32229(13) 0.0540(5) Uani 1 1 d . . . C12 C 0.2758(4) 0.4758(3) 0.6485(2) 0.0808(8) Uani 1 1 d . . . H12A H 0.1990 0.4951 0.6002 0.097 Uiso 1 1 calc R . . H12B H 0.2292 0.4112 0.6649 0.097 Uiso 1 1 calc R . . C13 C 0.5882(5) 0.4026(3) 0.69805(17) 0.0790(8) Uani 1 1 d . . . H13A H 0.5977 0.4403 0.7459 0.095 Uiso 1 1 calc R . . H13B H 0.5306 0.3367 0.7043 0.095 Uiso 1 1 calc R . . C11 C 0.2608(5) 0.5556(3) 0.7066(2) 0.0965(10) Uani 1 1 d . . . H11A H 0.1331 0.5646 0.7108 0.145 Uiso 1 1 calc R . . H11B H 0.3096 0.6192 0.6913 0.145 Uiso 1 1 calc R . . H11C H 0.3299 0.5347 0.7554 0.145 Uiso 1 1 calc R . . C14 C 0.7725(5) 0.3866(4) 0.6798(3) 0.1130(13) Uani 1 1 d . . . H14A H 0.8206 0.3219 0.7004 0.170 Uiso 1 1 calc R . . H14B H 0.8531 0.4410 0.7019 0.170 Uiso 1 1 calc R . . H14C H 0.7650 0.3865 0.6250 0.170 Uiso 1 1 calc R . . H2N H 0.482(4) 0.435(2) 0.6021(18) 0.058(8) Uiso 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 Cl1 0.0875(5) 0.0537(4) 0.1027(6) 0.0151(3) 0.0230(4) 0.0010(3) S1 0.0744(4) 0.0497(3) 0.0405(3) -0.0037(2) 0.0058(2) -0.0112(3) S2 0.1094(6) 0.0684(4) 0.0517(4) 0.0108(3) 0.0025(4) -0.0128(4) O1 0.0905(13) 0.0667(11) 0.0551(10) -0.0178(8) 0.0050(9) -0.0162(10) N2 0.0928(17) 0.0531(11) 0.0424(11) -0.0037(9) 0.0084(10) -0.0088(11) N1 0.0683(13) 0.0501(10) 0.0543(11) -0.0027(8) 0.0098(9) -0.0101(9) C1 0.0703(15) 0.0647(14) 0.0454(12) -0.0009(10) 0.0102(10) 0.0008(12) C2 0.0742(16) 0.0667(15) 0.0531(13) 0.0122(12) 0.0149(12) 0.0048(13) C3 0.0545(13) 0.0511(12) 0.0682(14) 0.0073(11) 0.0152(11) 0.0061(11) C4 0.0715(16) 0.0524(12) 0.0575(13) -0.0011(11) 0.0042(11) -0.0001(12) C5 0.0753(16) 0.0546(12) 0.0453(11) 0.0040(10) 0.0079(10) -0.0003(12) C6 0.0479(11) 0.0538(12) 0.0441(10) -0.0005(9) 0.0095(8) 0.0048(10) C7 0.0540(12) 0.0569(12) 0.0417(10) -0.0066(9) 0.0091(9) -0.0008(10) C8 0.0507(12) 0.0511(11) 0.0423(10) -0.0079(9) 0.0094(9) -0.0024(9) C9 0.0552(13) 0.0539(12) 0.0500(12) -0.0089(10) 0.0107(10) -0.0061(10) C10 0.0598(13) 0.0496(11) 0.0527(12) 0.0008(10) 0.0099(10) -0.0052(11) C12 0.0749(18) 0.0755(18) 0.090(2) 0.0084(16) 0.0097(15) -0.0067(15) C13 0.096(2) 0.0750(17) 0.0618(15) 0.0027(13) 0.0036(14) 0.0066(16) C11 0.100(2) 0.093(2) 0.104(3) 0.008(2) 0.039(2) 0.007(2) C14 0.088(2) 0.142(4) 0.106(3) -0.017(3) 0.007(2) 0.026(2) _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 Cl1 C3 1.739(2) . ? S1 C8 1.741(2) . ? S1 C10 1.767(2) . ? S2 C10 1.665(2) . ? O1 C9 1.226(3) . ? N2 C13 1.464(4) . ? N2 C12 1.530(4) . ? N2 H2N 0.69(3) . ? N1 C10 1.327(3) . ? N1 C9 1.368(3) . ? C1 C2 1.374(4) . ? C1 C6 1.398(3) . ? C1 H1A 0.9300 . ? C2 C3 1.372(4) . ? C2 H2A 0.9300 . ? C3 C4 1.370(4) . ? C4 C5 1.373(3) . ? C4 H4A 0.9300 . ? C5 C6 1.397(3) . ? C5 H5A 0.9300 . ? C6 C7 1.446(3) . ? C7 C8 1.348(3) . ? C7 H7A 0.9300 . ? C8 C9 1.486(3) . ? C12 C11 1.478(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.460(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 C8 S1 C10 90.75(11) . . ? C13 N2 C12 112.8(2) . . ? C13 N2 H2N 106(2) . . ? C12 N2 H2N 114(2) . . ? C10 N1 C9 113.08(19) . . ? C2 C1 C6 122.0(2) . . ? C2 C1 H1A 119.0 . . ? C6 C1 H1A 119.0 . . ? C3 C2 C1 119.0(2) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C4 C3 C2 121.3(2) . . ? C4 C3 Cl1 119.0(2) . . ? C2 C3 Cl1 119.7(2) . . ? C3 C4 C5 119.2(2) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? C4 C5 C6 121.9(2) . . ? C4 C5 H5A 119.0 . . ? C6 C5 H5A 119.0 . . ? C5 C6 C1 116.6(2) . . ? C5 C6 C7 124.8(2) . . ? C1 C6 C7 118.7(2) . . ? C8 C7 C6 130.4(2) . . ? C8 C7 H7A 114.8 . . ? C6 C7 H7A 114.8 . . ? C7 C8 C9 122.5(2) . . ? C7 C8 S1 129.65(17) . . ? C9 C8 S1 107.88(16) . . ? O1 C9 N1 123.6(2) . . ? O1 C9 C8 122.4(2) . . ? N1 C9 C8 114.02(19) . . ? N1 C10 S2 127.37(18) . . ? N1 C10 S1 114.25(17) . . ? S2 C10 S1 118.37(14) . . ? C11 C12 N2 112.5(3) . . ? C11 C12 H12A 109.1 . . ? N2 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? N2 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C14 C13 N2 109.4(3) . . ? C14 C13 H13A 109.8 . . ? N2 C13 H13A 109.8 . . ? C14 C13 H13B 109.8 . . ? N2 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 C6 C1 C2 C3 -0.8(4) . . . . ? C1 C2 C3 C4 1.1(4) . . . . ? C1 C2 C3 Cl1 -178.5(2) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? Cl1 C3 C4 C5 178.7(2) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C1 -0.1(4) . . . . ? C4 C5 C6 C7 -179.7(2) . . . . ? C2 C1 C6 C5 0.3(4) . . . . ? C2 C1 C6 C7 180.0(2) . . . . ? C5 C6 C7 C8 0.9(4) . . . . ? C1 C6 C7 C8 -178.7(2) . . . . ? C6 C7 C8 C9 -179.4(2) . . . . ? C6 C7 C8 S1 0.9(4) . . . . ? C10 S1 C8 C7 -179.7(2) . . . . ? C10 S1 C8 C9 0.56(17) . . . . ? C10 N1 C9 O1 -179.2(2) . . . . ? C10 N1 C9 C8 1.6(3) . . . . ? C7 C8 C9 O1 -0.2(4) . . . . ? S1 C8 C9 O1 179.5(2) . . . . ? C7 C8 C9 N1 179.0(2) . . . . ? S1 C8 C9 N1 -1.3(3) . . . . ? C9 N1 C10 S2 179.90(19) . . . . ? C9 N1 C10 S1 -1.2(3) . . . . ? C8 S1 C10 N1 0.3(2) . . . . ? C8 S1 C10 S2 179.35(16) . . . . ? C13 N2 C12 C11 75.9(3) . . . . ? C12 N2 C13 C14 177.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 70.26 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.450 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 930932'