# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Bhisma Patel' _publ_contact_author_email PATEL@IITG.ERNET.IN _publ_section_title ; Arylthioureas with Bromine or its Equivalents Gives No 'Hugerschoff' Reaction Product ; _publ_contact_author_address ? _publ_contact_author_phone 03612582307 loop_ _publ_author_name 'Bhisma Patel' 'Siva Murru' 'Abdur Rezzak Ali' 'Ramesh Yella' #---------------------------------------------------------------- data_6a _database_code_depnum_ccdc_archive 'CCDC 754857' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 Br2 N4 S' _chemical_formula_sum 'C24 H28 Br2 N4 S' _chemical_formula_weight 564.38 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' Br Br -0.2901 2.4595 '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/c' 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 9.2041(17) _cell_length_b 11.356(2) _cell_length_c 23.799(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.183(12) _cell_angle_gamma 90.00 _cell_volume 2483.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5166 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 21.47 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 1.509 _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 3.367 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.450 _exptl_absorpt_correction_T_max 0.714 _exptl_absorpt_process_details multi-scan _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 36388 _diffrn_reflns_av_R_equivalents 0.2249 _diffrn_reflns_av_sigmaI/netI 0.1754 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.40 _reflns_number_total 6128 _reflns_number_gt 2368 _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^)+(0.0100P)^2^+0.6910P] 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 6128 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1539 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1398 _refine_ls_wR_factor_gt 0.1170 _refine_ls_goodness_of_fit_ref 0.899 _refine_ls_restrained_S_all 0.899 _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 Br2 Br 0.07227(7) 1.16404(4) 0.09571(3) 0.0856(2) Uani 1 1 d . . . Br1 Br 0.30895(7) 0.39319(7) 0.34869(3) 0.1047(3) Uani 1 1 d . . . S5 S 0.13221(16) 0.44242(10) 0.05341(6) 0.0708(4) Uani 1 1 d . . . N3 N 0.4103(4) 0.6704(3) 0.03800(16) 0.0554(10) Uani 1 1 d . . . N1 N 0.4578(4) 0.5546(3) 0.11562(16) 0.0650(11) Uani 1 1 d . . . N2 N 0.2232(4) 0.6438(3) 0.09922(14) 0.0483(9) Uani 1 1 d . . . N4 N 0.0111(4) 0.5671(3) 0.13258(16) 0.0559(10) Uani 1 1 d . . . C17 C 0.5658(6) 0.6765(4) 0.0268(2) 0.0710(14) Uani 1 1 d . . . H1A H 0.5895 0.6152 0.0005 0.085 Uiso 1 1 calc R . . H1B H 0.6243 0.6644 0.0615 0.085 Uiso 1 1 calc R . . C16 C 0.5990(6) 0.7955(4) 0.0026(2) 0.0765(15) Uani 1 1 d . . . H2A H 0.6998 0.7973 -0.0073 0.092 Uiso 1 1 calc R . . H2B H 0.5864 0.8555 0.0310 0.092 Uiso 1 1 calc R . . C15 C 0.5012(6) 0.8244(5) -0.0496(2) 0.0805(16) Uani 1 1 d . . . H3A H 0.5194 0.9044 -0.0616 0.097 Uiso 1 1 calc R . . H3B H 0.5230 0.7716 -0.0800 0.097 Uiso 1 1 calc R . . C14 C 0.3423(6) 0.8114(4) -0.0362(2) 0.0746(15) Uani 1 1 d . . . H4A H 0.3175 0.8713 -0.0093 0.089 Uiso 1 1 calc R . . H4B H 0.2808 0.8227 -0.0702 0.089 Uiso 1 1 calc R . . C13 C 0.3150(5) 0.6914(4) -0.01218(19) 0.0600(12) Uani 1 1 d . . . H5A H 0.2142 0.6855 -0.0025 0.072 Uiso 1 1 calc R . . H5B H 0.3323 0.6318 -0.0402 0.072 Uiso 1 1 calc R . . C10 C 0.1127(6) 1.0024(4) 0.0979(2) 0.0626(13) Uani 1 1 d . . . C11 C 0.2425(6) 0.9642(4) 0.12447(19) 0.0604(12) Uani 1 1 d . . . H7 H 0.3066 1.0181 0.1417 0.072 Uiso 1 1 calc R . . C12 C 0.2754(5) 0.8457(4) 0.12509(19) 0.0558(12) Uani 1 1 d . . . H8 H 0.3619 0.8199 0.1431 0.067 Uiso 1 1 calc R . . C7 C 0.1817(5) 0.7652(3) 0.09931(18) 0.0480(11) Uani 1 1 d . . . C8 C 0.0538(5) 0.8042(3) 0.07308(19) 0.0553(12) Uani 1 1 d . . . H10 H -0.0102 0.7508 0.0554 0.066 Uiso 1 1 calc R . . C9 C 0.0207(6) 0.9224(4) 0.0730(2) 0.0637(13) Uani 1 1 d . . . H11 H -0.0666 0.9479 0.0556 0.076 Uiso 1 1 calc R . . C1 C 0.4192(5) 0.5196(4) 0.1690(2) 0.0618(13) Uani 1 1 d . . . C4 C 0.3576(6) 0.4420(5) 0.2761(2) 0.0682(14) Uani 1 1 d . . . C5 C 0.4037(6) 0.5568(5) 0.2684(2) 0.0754(15) Uani 1 1 d . . . H14 H 0.4139 0.6084 0.2987 0.090 Uiso 1 1 calc R . . C6 C 0.4341(6) 0.5929(4) 0.2150(2) 0.0720(15) Uani 1 1 d . . . H16 H 0.4658 0.6697 0.2099 0.086 Uiso 1 1 calc R . . C2 C 0.3745(6) 0.4043(4) 0.1793(2) 0.0678(14) Uani 1 1 d . . . H17 H 0.3647 0.3514 0.1494 0.081 Uiso 1 1 calc R . . C3 C 0.3446(6) 0.3674(4) 0.2322(2) 0.0731(15) Uani 1 1 d . . . H18 H 0.3151 0.2902 0.2378 0.088 Uiso 1 1 calc R . . C24 C 0.3687(5) 0.6168(3) 0.0844(2) 0.0513(11) Uani 1 1 d . . . C23 C 0.1201(5) 0.5535(3) 0.09805(18) 0.0519(11) Uani 1 1 d . . . C22 C 0.0205(6) 0.6370(4) 0.1844(2) 0.0673(14) Uani 1 1 d . . . H45A H -0.0492 0.7011 0.1813 0.081 Uiso 1 1 calc R . . H45B H 0.1171 0.6708 0.1896 0.081 Uiso 1 1 calc R . . C18 C -0.1266(6) 0.5028(4) 0.1244(2) 0.0758(15) Uani 1 1 d . . . H46A H -0.1252 0.4567 0.0901 0.091 Uiso 1 1 calc R . . H46B H -0.2059 0.5589 0.1199 0.091 Uiso 1 1 calc R . . C19 C -0.1533(7) 0.4232(5) 0.1724(3) 0.0973(19) Uani 1 1 d . . . H47A H -0.0786 0.3629 0.1753 0.117 Uiso 1 1 calc R . . H47B H -0.2468 0.3846 0.1660 0.117 Uiso 1 1 calc R . . C20 C -0.1518(7) 0.4928(6) 0.2265(3) 0.103(2) Uani 1 1 d . . . H48A H -0.1623 0.4397 0.2579 0.124 Uiso 1 1 calc R . . H48B H -0.2333 0.5471 0.2251 0.124 Uiso 1 1 calc R . . C21 C -0.0106(6) 0.5608(5) 0.2349(2) 0.0806(15) Uani 1 1 d . . . H49A H 0.0690 0.5057 0.2419 0.097 Uiso 1 1 calc R . . H49B H -0.0154 0.6106 0.2679 0.097 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 Br2 0.1040(5) 0.0418(3) 0.1136(5) 0.0058(3) 0.0304(4) 0.0139(3) Br1 0.0948(5) 0.1491(6) 0.0709(5) 0.0318(4) 0.0105(3) -0.0097(4) S5 0.0903(10) 0.0433(6) 0.0797(10) -0.0064(6) 0.0133(7) -0.0002(6) N3 0.056(3) 0.053(2) 0.058(3) 0.0143(19) 0.009(2) 0.0059(18) N1 0.067(3) 0.070(2) 0.060(3) 0.023(2) 0.013(2) 0.016(2) N2 0.046(2) 0.0374(18) 0.062(2) 0.0047(16) 0.0116(18) 0.0030(16) N4 0.048(3) 0.053(2) 0.066(3) 0.0073(19) 0.0047(19) -0.0072(18) C17 0.058(3) 0.080(3) 0.078(4) 0.016(3) 0.022(3) 0.012(3) C16 0.056(4) 0.090(3) 0.086(4) 0.007(3) 0.025(3) -0.010(3) C15 0.085(4) 0.085(3) 0.074(4) 0.020(3) 0.021(3) -0.002(3) C14 0.072(4) 0.078(3) 0.074(4) 0.022(3) 0.005(3) 0.006(3) C13 0.062(3) 0.066(3) 0.053(3) 0.004(2) 0.011(2) 0.001(2) C10 0.071(4) 0.046(2) 0.073(4) -0.001(2) 0.026(3) 0.001(2) C11 0.073(4) 0.044(2) 0.065(3) -0.001(2) 0.012(3) -0.004(2) C12 0.053(3) 0.051(3) 0.064(3) 0.006(2) 0.008(2) 0.001(2) C7 0.048(3) 0.038(2) 0.058(3) 0.000(2) 0.005(2) 0.001(2) C8 0.048(3) 0.044(2) 0.074(3) 0.007(2) 0.003(2) 0.000(2) C9 0.060(3) 0.053(3) 0.080(4) 0.015(2) 0.013(3) 0.012(2) C1 0.058(3) 0.063(3) 0.064(3) 0.014(3) -0.001(2) 0.017(2) C4 0.058(3) 0.089(4) 0.057(3) 0.020(3) -0.004(2) 0.010(3) C5 0.073(4) 0.087(4) 0.064(4) 0.002(3) -0.011(3) -0.002(3) C6 0.076(4) 0.072(3) 0.067(4) 0.018(3) -0.003(3) -0.011(3) C2 0.081(4) 0.055(3) 0.068(4) 0.008(3) 0.007(3) 0.012(3) C3 0.086(4) 0.061(3) 0.072(4) 0.026(3) 0.003(3) 0.001(3) C24 0.049(3) 0.043(2) 0.063(3) 0.009(2) 0.013(2) 0.004(2) C23 0.053(3) 0.042(2) 0.061(3) 0.016(2) 0.009(2) 0.006(2) C22 0.067(4) 0.066(3) 0.070(4) -0.009(3) 0.015(3) 0.005(3) C18 0.067(4) 0.078(3) 0.082(4) -0.003(3) 0.005(3) -0.008(3) C19 0.081(4) 0.097(4) 0.116(6) 0.013(4) 0.025(4) -0.027(3) C20 0.092(5) 0.129(5) 0.092(5) 0.018(4) 0.034(4) -0.022(4) C21 0.071(4) 0.108(4) 0.065(4) 0.006(3) 0.023(3) 0.004(3) _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 Br2 C10 1.873(4) . ? Br1 C4 1.892(5) . ? S5 C23 1.657(5) . ? N3 C24 1.334(5) . ? N3 C13 1.462(5) . ? N3 C17 1.472(6) . ? N1 C24 1.287(5) . ? N1 C1 1.396(6) . ? N2 C23 1.396(5) . ? N2 C7 1.431(5) . ? N2 C24 1.437(5) . ? N4 C23 1.341(6) . ? N4 C22 1.465(6) . ? N4 C18 1.466(6) . ? C17 C16 1.507(6) . ? C17 H1A 0.9700 . ? C17 H1B 0.9700 . ? C16 C15 1.528(7) . ? C16 H2A 0.9700 . ? C16 H2B 0.9700 . ? C15 C14 1.522(7) . ? C15 H3A 0.9700 . ? C15 H3B 0.9700 . ? C14 C13 1.504(6) . ? C14 H4A 0.9700 . ? C14 H4B 0.9700 . ? C13 H5A 0.9700 . ? C13 H5B 0.9700 . ? C10 C9 1.355(6) . ? C10 C11 1.390(7) . ? C11 C12 1.379(6) . ? C11 H7 0.9300 . ? C12 C7 1.378(6) . ? C12 H8 0.9300 . ? C7 C8 1.374(6) . ? C8 C9 1.376(6) . ? C8 H10 0.9300 . ? C9 H11 0.9300 . ? C1 C6 1.375(7) . ? C1 C2 1.399(6) . ? C4 C3 1.345(7) . ? C4 C5 1.386(7) . ? C5 C6 1.379(6) . ? C5 H14 0.9300 . ? C6 H16 0.9300 . ? C2 C3 1.370(6) . ? C2 H17 0.9300 . ? C3 H18 0.9300 . ? C22 C21 1.522(6) . ? C22 H45A 0.9700 . ? C22 H45B 0.9700 . ? C18 C19 1.489(7) . ? C18 H46A 0.9700 . ? C18 H46B 0.9700 . ? C19 C20 1.509(8) . ? C19 H47A 0.9700 . ? C19 H47B 0.9700 . ? C20 C21 1.517(8) . ? C20 H48A 0.9700 . ? C20 H48B 0.9700 . ? C21 H49A 0.9700 . ? C21 H49B 0.9700 . ? 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 C24 N3 C13 124.3(4) . . ? C24 N3 C17 119.8(4) . . ? C13 N3 C17 113.0(4) . . ? C24 N1 C1 119.8(4) . . ? C23 N2 C7 121.7(3) . . ? C23 N2 C24 118.7(3) . . ? C7 N2 C24 117.3(3) . . ? C23 N4 C22 124.5(4) . . ? C23 N4 C18 122.2(4) . . ? C22 N4 C18 113.1(4) . . ? N3 C17 C16 109.3(4) . . ? N3 C17 H1A 109.8 . . ? C16 C17 H1A 109.8 . . ? N3 C17 H1B 109.8 . . ? C16 C17 H1B 109.8 . . ? H1A C17 H1B 108.3 . . ? C17 C16 C15 112.4(5) . . ? C17 C16 H2A 109.1 . . ? C15 C16 H2A 109.1 . . ? C17 C16 H2B 109.1 . . ? C15 C16 H2B 109.1 . . ? H2A C16 H2B 107.9 . . ? C14 C15 C16 109.8(4) . . ? C14 C15 H3A 109.7 . . ? C16 C15 H3A 109.7 . . ? C14 C15 H3B 109.7 . . ? C16 C15 H3B 109.7 . . ? H3A C15 H3B 108.2 . . ? C13 C14 C15 110.5(4) . . ? C13 C14 H4A 109.5 . . ? C15 C14 H4A 109.5 . . ? C13 C14 H4B 109.5 . . ? C15 C14 H4B 109.5 . . ? H4A C14 H4B 108.1 . . ? N3 C13 C14 110.6(4) . . ? N3 C13 H5A 109.5 . . ? C14 C13 H5A 109.5 . . ? N3 C13 H5B 109.5 . . ? C14 C13 H5B 109.5 . . ? H5A C13 H5B 108.1 . . ? C9 C10 C11 119.4(4) . . ? C9 C10 Br2 121.8(4) . . ? C11 C10 Br2 118.8(4) . . ? C12 C11 C10 119.5(4) . . ? C12 C11 H7 120.3 . . ? C10 C11 H7 120.3 . . ? C7 C12 C11 120.7(4) . . ? C7 C12 H8 119.6 . . ? C11 C12 H8 119.6 . . ? C8 C7 C12 119.2(4) . . ? C8 C7 N2 122.2(4) . . ? C12 C7 N2 118.7(4) . . ? C7 C8 C9 119.9(4) . . ? C7 C8 H10 120.0 . . ? C9 C8 H10 120.0 . . ? C10 C9 C8 121.4(5) . . ? C10 C9 H11 119.3 . . ? C8 C9 H11 119.3 . . ? C6 C1 N1 122.2(4) . . ? C6 C1 C2 116.4(5) . . ? N1 C1 C2 121.2(5) . . ? C3 C4 C5 120.3(5) . . ? C3 C4 Br1 120.7(4) . . ? C5 C4 Br1 119.0(4) . . ? C6 C5 C4 118.7(5) . . ? C6 C5 H14 120.6 . . ? C4 C5 H14 120.6 . . ? C1 C6 C5 122.5(5) . . ? C1 C6 H16 118.8 . . ? C5 C6 H16 118.8 . . ? C3 C2 C1 121.5(5) . . ? C3 C2 H17 119.3 . . ? C1 C2 H17 119.3 . . ? C4 C3 C2 120.6(5) . . ? C4 C3 H18 119.7 . . ? C2 C3 H18 119.7 . . ? N1 C24 N3 121.7(4) . . ? N1 C24 N2 123.2(4) . . ? N3 C24 N2 114.9(4) . . ? N4 C23 N2 115.8(4) . . ? N4 C23 S5 124.0(4) . . ? N2 C23 S5 120.1(3) . . ? N4 C22 C21 110.6(4) . . ? N4 C22 H45A 109.5 . . ? C21 C22 H45A 109.5 . . ? N4 C22 H45B 109.5 . . ? C21 C22 H45B 109.5 . . ? H45A C22 H45B 108.1 . . ? N4 C18 C19 112.3(4) . . ? N4 C18 H46A 109.1 . . ? C19 C18 H46A 109.1 . . ? N4 C18 H46B 109.1 . . ? C19 C18 H46B 109.1 . . ? H46A C18 H46B 107.9 . . ? C18 C19 C20 110.0(5) . . ? C18 C19 H47A 109.7 . . ? C20 C19 H47A 109.7 . . ? C18 C19 H47B 109.7 . . ? C20 C19 H47B 109.7 . . ? H47A C19 H47B 108.2 . . ? C19 C20 C21 110.3(5) . . ? C19 C20 H48A 109.6 . . ? C21 C20 H48A 109.6 . . ? C19 C20 H48B 109.6 . . ? C21 C20 H48B 109.6 . . ? H48A C20 H48B 108.1 . . ? C20 C21 C22 112.4(4) . . ? C20 C21 H49A 109.1 . . ? C22 C21 H49A 109.1 . . ? C20 C21 H49B 109.1 . . ? C22 C21 H49B 109.1 . . ? H49A C21 H49B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.598 _refine_diff_density_min -1.197 _refine_diff_density_rms 0.111 #--------------------------------------------------------- data_5b _database_code_depnum_ccdc_archive 'CCDC 754858' loop_ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 Cl2 N4 O2 S' _chemical_formula_sum 'C22 H24 Cl2 N4 O2 S' _chemical_formula_weight 479.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' 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 9.1161(6) _cell_length_b 11.1981(6) _cell_length_c 22.7023(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.02 _cell_angle_gamma 90.00 _cell_volume 2317.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6178 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 23.85 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 1.374 _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000.0 _exptl_absorpt_coefficient_mu 0.397 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28642 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 24.25 _reflns_number_total 3718 _reflns_number_gt 2603 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.1173P] 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 3718 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1186 _refine_ls_goodness_of_fit_ref 0.842 _refine_ls_restrained_S_all 0.842 _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 0.11748(8) 0.55428(6) 0.05620(3) 0.0684(3) Uani 1 1 d . . . Cl2 Cl 0.04201(10) -0.15995(6) 0.09245(4) 0.0852(3) Uani 1 1 d . . . Cl1 Cl 0.32772(10) 0.62306(9) 0.35023(3) 0.0971(3) Uani 1 1 d . . . N1 N 0.4507(2) 0.44549(17) 0.11004(9) 0.0548(5) Uani 1 1 d . . . N3 N 0.4092(2) 0.32033(16) 0.03126(8) 0.0504(5) Uani 1 1 d . . . N2 N 0.2180(2) 0.34911(14) 0.09889(8) 0.0457(5) Uani 1 1 d . . . C21 C 0.3643(3) 0.37815(19) 0.08080(10) 0.0458(6) Uani 1 1 d . . . N4 N 0.0086(2) 0.42369(18) 0.14343(9) 0.0618(6) Uani 1 1 d . . . C16 C 0.5648(3) 0.3154(2) 0.01746(12) 0.0612(7) Uani 1 1 d . . . H5A H 0.6222 0.3197 0.0534 0.073 Uiso 1 1 calc R . . H5B H 0.5917 0.3823 -0.0075 0.073 Uiso 1 1 calc R . . C12 C 0.2648(3) 0.14004(19) 0.12107(11) 0.0544(6) Uani 1 1 d . . . H6 H 0.3532 0.1620 0.1384 0.065 Uiso 1 1 calc R . . C1 C 0.4142(3) 0.4853(2) 0.16708(10) 0.0523(6) Uani 1 1 d . . . C22 C 0.1123(3) 0.44060(18) 0.10204(10) 0.0481(6) Uani 1 1 d . . . C7 C 0.1731(3) 0.22636(19) 0.09745(10) 0.0469(6) Uani 1 1 d . . . C8 C 0.0420(3) 0.1935(2) 0.07176(11) 0.0555(6) Uani 1 1 d . . . H10 H -0.0183 0.2514 0.0552 0.067 Uiso 1 1 calc R . . C9 C -0.0004(3) 0.0748(2) 0.07053(12) 0.0632(7) Uani 1 1 d . . . H11 H -0.0894 0.0526 0.0538 0.076 Uiso 1 1 calc R . . C2 C 0.4270(3) 0.4109(2) 0.21541(12) 0.0651(7) Uani 1 1 d . . . H12 H 0.4530 0.3313 0.2100 0.078 Uiso 1 1 calc R . . C6 C 0.3784(3) 0.6044(2) 0.17603(11) 0.0605(7) Uani 1 1 d . . . H13 H 0.3733 0.6563 0.1441 0.073 Uiso 1 1 calc R . . O1 O 0.5065(2) 0.18518(18) -0.06525(9) 0.0840(6) Uani 1 1 d . . . C5 C 0.3502(3) 0.6460(2) 0.23218(13) 0.0664(7) Uani 1 1 d . . . H15 H 0.3231 0.7251 0.2380 0.080 Uiso 1 1 calc R . . C13 C 0.3163(3) 0.3057(2) -0.02109(11) 0.0594(7) Uani 1 1 d . . . H16A H 0.3317 0.3718 -0.0480 0.071 Uiso 1 1 calc R . . H16B H 0.2137 0.3050 -0.0097 0.071 Uiso 1 1 calc R . . C14 C 0.3554(3) 0.1901(3) -0.05075(13) 0.0774(8) Uani 1 1 d . . . H17A H 0.3314 0.1241 -0.0248 0.093 Uiso 1 1 calc R . . H17B H 0.2976 0.1815 -0.0864 0.093 Uiso 1 1 calc R . . C10 C 0.0919(3) -0.0101(2) 0.09460(12) 0.0610(7) Uani 1 1 d . . . C3 C 0.4018(3) 0.4531(3) 0.27175(13) 0.0721(8) Uani 1 1 d . . . H19 H 0.4113 0.4028 0.3041 0.086 Uiso 1 1 calc R . . C4 C 0.3625(3) 0.5702(3) 0.27924(12) 0.0647(7) Uani 1 1 d . . . C15 C 0.5945(3) 0.1996(3) -0.01396(14) 0.0771(8) Uani 1 1 d . . . H21A H 0.6972 0.1966 -0.0251 0.093 Uiso 1 1 calc R . . H21B H 0.5758 0.1338 0.0128 0.093 Uiso 1 1 calc R . . C20 C 0.0236(4) 0.3479(3) 0.19554(12) 0.0783(9) Uani 1 1 d . . . H22A H -0.0377 0.2777 0.1912 0.094 Uiso 1 1 calc R . . H22B H 0.1246 0.3217 0.1992 0.094 Uiso 1 1 calc R . . C17 C -0.1344(3) 0.4848(3) 0.14038(16) 0.0914(10) Uani 1 1 d . . . H23A H -0.2105 0.4276 0.1307 0.110 Uiso 1 1 calc R . . H23B H -0.1320 0.5449 0.1096 0.110 Uiso 1 1 calc R . . C11 C 0.2244(3) 0.0213(2) 0.11876(12) 0.0619(7) Uani 1 1 d . . . H24 H 0.2868 -0.0372 0.1335 0.074 Uiso 1 1 calc R . . O2 O -0.1629(3) 0.4574(4) 0.24408(13) 0.1437(13) Uani 1 1 d . . . C19 C -0.0192(4) 0.4130(4) 0.24850(16) 0.1257(15) Uani 1 1 d . . . H26A H -0.0125 0.3602 0.2823 0.151 Uiso 1 1 calc R . . H26B H 0.0481 0.4789 0.2547 0.151 Uiso 1 1 calc R . . C18 C -0.1682(5) 0.5423(4) 0.1978(2) 0.1342(17) Uani 1 1 d . . . H27A H -0.0977 0.6054 0.2054 0.161 Uiso 1 1 calc R . . H27B H -0.2651 0.5779 0.1962 0.161 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 0.0754(5) 0.0471(4) 0.0828(5) 0.0114(3) -0.0026(4) 0.0002(3) Cl2 0.1117(7) 0.0457(4) 0.0984(6) -0.0099(3) 0.0275(5) -0.0211(4) Cl1 0.0941(6) 0.1348(8) 0.0624(5) -0.0324(5) 0.0112(4) -0.0035(5) N1 0.0582(13) 0.0538(11) 0.0523(12) -0.0088(10) 0.0069(10) -0.0096(10) N3 0.0527(12) 0.0511(11) 0.0473(12) -0.0061(9) 0.0089(9) -0.0045(9) N2 0.0494(12) 0.0368(9) 0.0508(11) -0.0028(8) 0.0079(9) -0.0011(8) C21 0.0524(14) 0.0393(12) 0.0457(13) 0.0011(10) 0.0084(11) -0.0015(10) N4 0.0613(13) 0.0601(12) 0.0639(14) -0.0011(10) 0.0140(11) 0.0145(10) C16 0.0563(16) 0.0625(15) 0.0649(17) -0.0036(13) 0.0164(13) -0.0040(12) C12 0.0541(15) 0.0453(13) 0.0637(16) 0.0029(11) 0.0046(12) -0.0022(11) C1 0.0471(14) 0.0568(14) 0.0529(15) -0.0081(12) 0.0012(11) -0.0093(11) C22 0.0533(14) 0.0406(12) 0.0505(14) -0.0079(10) 0.0013(12) 0.0000(10) C7 0.0507(14) 0.0413(12) 0.0488(13) -0.0027(10) 0.0115(11) -0.0022(10) C8 0.0544(16) 0.0500(14) 0.0622(16) -0.0079(12) 0.0051(13) 0.0006(11) C9 0.0600(16) 0.0548(15) 0.0749(18) -0.0152(13) 0.0092(14) -0.0113(12) C2 0.0772(19) 0.0595(15) 0.0587(17) -0.0049(13) 0.0017(14) 0.0085(13) C6 0.0719(18) 0.0518(14) 0.0577(16) -0.0058(12) -0.0001(13) -0.0080(12) O1 0.0875(15) 0.0937(14) 0.0709(14) -0.0264(11) 0.0214(12) 0.0048(11) C5 0.0699(18) 0.0612(16) 0.0682(19) -0.0205(14) 0.0006(14) -0.0044(13) C13 0.0677(17) 0.0613(15) 0.0491(15) -0.0034(12) 0.0059(13) -0.0029(12) C14 0.083(2) 0.082(2) 0.0672(19) -0.0239(15) 0.0099(16) -0.0083(15) C10 0.0726(19) 0.0427(13) 0.0678(17) -0.0067(12) 0.0219(14) -0.0100(12) C3 0.076(2) 0.085(2) 0.0554(17) 0.0030(14) -0.0043(14) 0.0023(15) C4 0.0553(16) 0.086(2) 0.0530(16) -0.0176(15) 0.0038(13) -0.0075(14) C15 0.072(2) 0.0792(19) 0.080(2) -0.0119(16) 0.0162(17) 0.0127(15) C20 0.085(2) 0.091(2) 0.0591(18) 0.0061(15) 0.0193(15) 0.0102(16) C17 0.070(2) 0.094(2) 0.110(3) -0.005(2) 0.0119(18) 0.0249(17) C11 0.0708(19) 0.0424(13) 0.0725(17) 0.0033(12) 0.0103(14) 0.0052(12) O2 0.090(2) 0.249(4) 0.0926(19) -0.026(2) 0.0310(16) 0.043(2) C19 0.099(3) 0.206(5) 0.073(2) -0.025(3) 0.014(2) 0.030(3) C18 0.088(3) 0.150(4) 0.165(5) -0.061(4) 0.021(3) 0.036(3) _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 C22 1.645(2) . ? Cl2 C10 1.740(2) . ? Cl1 C4 1.746(3) . ? N1 C21 1.277(3) . ? N1 C1 1.409(3) . ? N3 C21 1.361(3) . ? N3 C16 1.454(3) . ? N3 C13 1.468(3) . ? N2 C22 1.408(3) . ? N2 C21 1.433(3) . ? N2 C7 1.434(3) . ? N4 C22 1.346(3) . ? N4 C20 1.462(3) . ? N4 C17 1.474(3) . ? C16 C15 1.505(4) . ? C12 C11 1.381(3) . ? C12 C7 1.386(3) . ? C1 C2 1.383(3) . ? C1 C6 1.388(3) . ? C7 C8 1.380(3) . ? C8 C9 1.384(3) . ? C9 C10 1.382(4) . ? C2 C3 1.383(4) . ? C6 C5 1.381(4) . ? O1 C14 1.417(3) . ? O1 C15 1.423(3) . ? C5 C4 1.369(4) . ? C13 C14 1.502(3) . ? C10 C11 1.372(4) . ? C3 C4 1.369(4) . ? C20 C19 1.459(4) . ? C17 C18 1.486(5) . ? O2 C19 1.405(4) . ? O2 C18 1.418(6) . ? 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 C21 N1 C1 121.22(19) . . ? C21 N3 C16 119.32(19) . . ? C21 N3 C13 123.26(19) . . ? C16 N3 C13 112.59(19) . . ? C22 N2 C21 119.09(17) . . ? C22 N2 C7 120.22(18) . . ? C21 N2 C7 118.44(17) . . ? N1 C21 N3 121.7(2) . . ? N1 C21 N2 124.0(2) . . ? N3 C21 N2 114.14(19) . . ? C22 N4 C20 125.5(2) . . ? C22 N4 C17 121.5(2) . . ? C20 N4 C17 113.0(2) . . ? N3 C16 C15 108.1(2) . . ? C11 C12 C7 119.7(2) . . ? C2 C1 C6 118.9(2) . . ? C2 C1 N1 121.3(2) . . ? C6 C1 N1 119.6(2) . . ? N4 C22 N2 114.43(19) . . ? N4 C22 S1 124.79(17) . . ? N2 C22 S1 120.75(17) . . ? C8 C7 C12 120.0(2) . . ? C8 C7 N2 120.8(2) . . ? C12 C7 N2 119.2(2) . . ? C7 C8 C9 120.4(2) . . ? C10 C9 C8 118.9(2) . . ? C1 C2 C3 120.9(2) . . ? C5 C6 C1 120.2(3) . . ? C14 O1 C15 110.7(2) . . ? C4 C5 C6 119.7(3) . . ? N3 C13 C14 108.8(2) . . ? O1 C14 C13 111.6(2) . . ? C11 C10 C9 121.2(2) . . ? C11 C10 Cl2 119.2(2) . . ? C9 C10 Cl2 119.6(2) . . ? C4 C3 C2 119.1(3) . . ? C5 C4 C3 121.2(3) . . ? C5 C4 Cl1 119.7(2) . . ? C3 C4 Cl1 119.1(2) . . ? O1 C15 C16 112.6(2) . . ? C19 C20 N4 110.6(3) . . ? N4 C17 C18 110.1(3) . . ? C10 C11 C12 119.8(2) . . ? C19 O2 C18 108.8(3) . . ? O2 C19 C20 111.6(3) . . ? O2 C18 C17 110.7(4) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 24.25 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.322 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.038 # Attachment 'combined_cif.txt' data_1a _database_code_depnum_ccdc_archive 'CCDC 754859' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 N4 S' _chemical_formula_weight 406.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 'P2(1)/c ' 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 9.5428(10) _cell_length_b 10.2273(11) _cell_length_c 22.766(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.034(6) _cell_angle_gamma 90.00 _cell_volume 2209.6(4) _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 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.961 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details multi-scan _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 28446 _diffrn_reflns_av_R_equivalents 0.1648 _diffrn_reflns_av_sigmaI/netI 0.0824 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 28.20 _reflns_number_total 5335 _reflns_number_gt 3394 _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^)+(0.1528P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5335 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1001 _refine_ls_R_factor_gt 0.0676 _refine_ls_wR_factor_ref 0.2551 _refine_ls_wR_factor_gt 0.1946 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.16302(7) -0.08604(7) 0.05828(3) 0.0621(3) Uani 1 1 d . . . N3 N 0.41576(18) 0.17773(19) 0.05604(8) 0.0471(5) Uani 1 1 d . . . N4 N 0.01455(18) 0.0439(2) 0.13265(8) 0.0493(5) Uani 1 1 d . . . C17 C 0.5671(2) 0.1803(3) 0.05070(12) 0.0557(6) Uani 1 1 d . . . H5A H 0.5927 0.1049 0.0283 0.067 Uiso 1 1 calc R . . H5B H 0.6188 0.1757 0.0897 0.067 Uiso 1 1 calc R . . C13 C 0.3280(2) 0.1939(2) -0.00037(10) 0.0492(6) Uani 1 1 d . . . H1A H 0.2293 0.1926 0.0064 0.059 Uiso 1 1 calc R . . H1B H 0.3446 0.1217 -0.0264 0.059 Uiso 1 1 calc R . . C14 C 0.3614(3) 0.3211(3) -0.02935(11) 0.0570(6) Uani 1 1 d . . . H2A H 0.3376 0.3937 -0.0049 0.068 Uiso 1 1 calc R . . H2B H 0.3056 0.3285 -0.0674 0.068 Uiso 1 1 calc R . . C22 C 0.0021(3) 0.1239(3) 0.18481(11) 0.0585(7) Uani 1 1 d . . . H10A H -0.0700 0.1898 0.1758 0.070 Uiso 1 1 calc R . . H10B H 0.0907 0.1682 0.1960 0.070 Uiso 1 1 calc R . . C16 C 0.6066(3) 0.3042(3) 0.02007(13) 0.0615(7) Uani 1 1 d . . . H4A H 0.5957 0.3781 0.0459 0.074 Uiso 1 1 calc R . . H4B H 0.7049 0.2994 0.0130 0.074 Uiso 1 1 calc R . . C15 C 0.5180(3) 0.3263(3) -0.03780(12) 0.0660(7) Uani 1 1 d . . . H3A H 0.5393 0.2598 -0.0659 0.079 Uiso 1 1 calc R . . H3B H 0.5403 0.4110 -0.0536 0.079 Uiso 1 1 calc R . . C18 C -0.1106(3) -0.0365(3) 0.11514(12) 0.0647(7) Uani 1 1 d . . . H6A H -0.0929 -0.0911 0.0819 0.078 Uiso 1 1 calc R . . H6B H -0.1897 0.0201 0.1027 0.078 Uiso 1 1 calc R . . C21 C -0.0355(4) 0.0408(3) 0.23536(13) 0.0767(9) Uani 1 1 d . . . H9A H -0.0519 0.0971 0.2683 0.092 Uiso 1 1 calc R . . H9B H 0.0433 -0.0159 0.2481 0.092 Uiso 1 1 calc R . . C20 C -0.1656(4) -0.0422(4) 0.21906(15) 0.0927(11) Uani 1 1 d . . . H8A H -0.1803 -0.1004 0.2515 0.111 Uiso 1 1 calc R . . H8B H -0.2477 0.0136 0.2118 0.111 Uiso 1 1 calc R . . C19 C -0.1470(4) -0.1208(4) 0.16474(15) 0.0862(10) Uani 1 1 d . . . H7A H -0.0727 -0.1847 0.1739 0.103 Uiso 1 1 calc R . . H7B H -0.2334 -0.1679 0.1526 0.103 Uiso 1 1 calc R . . C1 C 0.4015(2) 0.0131(3) 0.19530(11) 0.0531(6) Uani 1 1 d . . . C2 C 0.3858(3) 0.0992(3) 0.24131(12) 0.0722(8) Uani 1 1 d . . . H12 H 0.3982 0.1886 0.2364 0.087 Uiso 1 1 calc R . . C6 C 0.3805(3) -0.1170(3) 0.20425(14) 0.0735(8) Uani 1 1 d . . . H16 H 0.3913 -0.1757 0.1738 0.088 Uiso 1 1 calc R . . C4 C 0.3283(4) -0.0806(4) 0.30286(15) 0.0856(10) Uani 1 1 d . . . H14 H 0.3030 -0.1115 0.3387 0.103 Uiso 1 1 calc R . . C5 C 0.3432(4) -0.1639(4) 0.25766(17) 0.0898(11) Uani 1 1 d . . . H15 H 0.3283 -0.2530 0.2624 0.108 Uiso 1 1 calc R . . C3 C 0.3514(4) 0.0500(4) 0.29481(14) 0.0900(11) Uani 1 1 d . . . H13 H 0.3437 0.1073 0.3260 0.108 Uiso 1 1 calc R . . C7 C 0.1742(2) 0.2777(2) 0.10653(10) 0.0450(5) Uani 1 1 d . . . C12 C 0.2610(3) 0.3749(3) 0.13166(10) 0.0536(6) Uani 1 1 d . . . H22 H 0.3476 0.3536 0.1520 0.064 Uiso 1 1 calc R . . C8 C 0.0450(3) 0.3108(3) 0.07599(12) 0.0580(6) Uani 1 1 d . . . H18 H -0.0132 0.2460 0.0581 0.070 Uiso 1 1 calc R . . C11 C 0.2182(3) 0.5056(3) 0.12639(13) 0.0693(8) Uani 1 1 d . . . H21 H 0.2769 0.5715 0.1428 0.083 Uiso 1 1 calc R . . C10 C 0.0906(4) 0.5362(3) 0.09720(15) 0.0784(9) Uani 1 1 d . . . H20 H 0.0621 0.6231 0.0941 0.094 Uiso 1 1 calc R . . C9 C 0.0037(4) 0.4395(3) 0.07234(16) 0.0771(9) Uani 1 1 d . . . H19 H -0.0838 0.4613 0.0529 0.093 Uiso 1 1 calc R . . N2 N 0.22101(16) 0.14376(19) 0.10997(8) 0.0432(5) Uani 1 1 d . . . N1 N 0.4491(2) 0.0556(2) 0.14119(9) 0.0551(6) Uani 1 1 d . . . C24 C 0.3683(2) 0.1193(2) 0.10359(10) 0.0451(5) Uani 1 1 d . . . C23 C 0.1288(2) 0.0380(2) 0.10279(9) 0.0457(5) 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 0.0640(4) 0.0603(5) 0.0648(5) -0.0149(3) 0.0205(3) -0.0059(3) N3 0.0362(9) 0.0575(13) 0.0483(11) 0.0062(8) 0.0077(7) -0.0006(8) N4 0.0406(9) 0.0638(13) 0.0447(10) -0.0027(9) 0.0102(7) -0.0085(8) C17 0.0378(11) 0.0624(16) 0.0691(16) 0.0022(12) 0.0155(10) 0.0049(10) C13 0.0484(12) 0.0588(15) 0.0409(12) -0.0014(10) 0.0064(9) -0.0028(10) C14 0.0637(15) 0.0626(17) 0.0457(13) 0.0046(11) 0.0109(11) 0.0004(12) C22 0.0601(14) 0.0643(17) 0.0547(15) -0.0085(12) 0.0232(11) -0.0061(12) C16 0.0469(13) 0.0641(17) 0.0768(18) -0.0010(13) 0.0220(12) -0.0071(11) C15 0.0733(17) 0.0641(18) 0.0654(17) 0.0035(13) 0.0298(13) -0.0105(13) C18 0.0449(12) 0.089(2) 0.0601(16) -0.0027(14) 0.0050(11) -0.0168(12) C21 0.086(2) 0.097(2) 0.0507(16) -0.0047(15) 0.0221(14) -0.0158(17) C20 0.095(2) 0.118(3) 0.071(2) -0.0025(19) 0.0387(17) -0.044(2) C19 0.094(2) 0.084(2) 0.084(2) -0.0013(17) 0.0252(17) -0.0409(19) C1 0.0426(11) 0.0617(16) 0.0538(14) 0.0150(11) -0.0009(9) 0.0048(10) C2 0.0852(19) 0.078(2) 0.0520(16) 0.0050(14) -0.0013(13) -0.0054(15) C6 0.088(2) 0.0614(19) 0.0734(19) 0.0144(15) 0.0174(15) 0.0086(15) C4 0.090(2) 0.106(3) 0.0603(19) 0.0357(18) 0.0096(16) 0.014(2) C5 0.097(2) 0.089(3) 0.087(2) 0.037(2) 0.0222(19) 0.0092(19) C3 0.107(3) 0.115(3) 0.0469(17) -0.0006(17) 0.0008(15) 0.012(2) C7 0.0458(11) 0.0480(13) 0.0434(11) 0.0026(9) 0.0145(9) 0.0011(9) C12 0.0569(13) 0.0580(16) 0.0483(13) -0.0053(11) 0.0164(10) -0.0115(11) C8 0.0547(14) 0.0508(15) 0.0684(16) 0.0112(12) 0.0057(11) 0.0052(11) C11 0.096(2) 0.0514(16) 0.0667(17) -0.0108(13) 0.0363(15) -0.0171(15) C10 0.100(2) 0.0507(17) 0.090(2) 0.0144(16) 0.0364(19) 0.0166(16) C9 0.0704(18) 0.074(2) 0.089(2) 0.0214(17) 0.0148(15) 0.0151(16) N2 0.0353(9) 0.0506(12) 0.0441(10) 0.0017(8) 0.0066(7) -0.0018(7) N1 0.0423(10) 0.0688(15) 0.0546(12) 0.0154(10) 0.0065(8) 0.0052(9) C24 0.0362(10) 0.0523(13) 0.0472(12) -0.0010(10) 0.0065(8) -0.0016(9) C23 0.0381(10) 0.0608(15) 0.0382(11) 0.0044(9) 0.0043(8) -0.0001(9) _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 C23 1.677(2) . ? N3 C24 1.355(3) . ? N3 C17 1.463(3) . ? N3 C13 1.467(3) . ? N4 C23 1.345(3) . ? N4 C22 1.457(3) . ? N4 C18 1.470(3) . ? C17 C16 1.513(3) . ? C13 C14 1.508(3) . ? C14 C15 1.527(3) . ? C22 C21 1.504(4) . ? C16 C15 1.506(4) . ? C18 C19 1.491(4) . ? C21 C20 1.518(4) . ? C20 C19 1.501(4) . ? C1 C6 1.365(4) . ? C1 C2 1.388(4) . ? C1 N1 1.425(3) . ? C2 C3 1.389(4) . ? C6 C5 1.388(4) . ? C4 C5 1.355(5) . ? C4 C3 1.369(5) . ? C7 C12 1.379(3) . ? C7 C8 1.392(3) . ? C7 N2 1.440(3) . ? C12 C11 1.399(4) . ? C8 C9 1.374(4) . ? C11 C10 1.361(5) . ? C10 C9 1.375(5) . ? N2 C23 1.393(3) . ? N2 C24 1.450(2) . ? N1 C24 1.270(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 C24 N3 C17 119.36(19) . . ? C24 N3 C13 122.73(17) . . ? C17 N3 C13 113.78(18) . . ? C23 N4 C22 125.22(19) . . ? C23 N4 C18 121.1(2) . . ? C22 N4 C18 113.68(19) . . ? N3 C17 C16 110.4(2) . . ? N3 C13 C14 110.65(19) . . ? C13 C14 C15 109.9(2) . . ? N4 C22 C21 110.7(2) . . ? C15 C16 C17 112.7(2) . . ? C16 C15 C14 110.6(2) . . ? N4 C18 C19 111.4(2) . . ? C22 C21 C20 112.6(3) . . ? C19 C20 C21 109.7(2) . . ? C18 C19 C20 111.8(3) . . ? C6 C1 C2 118.5(3) . . ? C6 C1 N1 119.5(3) . . ? C2 C1 N1 121.9(3) . . ? C1 C2 C3 119.1(3) . . ? C1 C6 C5 121.5(3) . . ? C5 C4 C3 118.7(3) . . ? C4 C5 C6 120.3(3) . . ? C4 C3 C2 121.8(3) . . ? C12 C7 C8 119.6(2) . . ? C12 C7 N2 119.6(2) . . ? C8 C7 N2 120.8(2) . . ? C7 C12 C11 119.7(3) . . ? C9 C8 C7 119.8(3) . . ? C10 C11 C12 120.0(3) . . ? C11 C10 C9 120.3(3) . . ? C8 C9 C10 120.5(3) . . ? C23 N2 C7 122.90(18) . . ? C23 N2 C24 117.48(18) . . ? C7 N2 C24 117.21(17) . . ? C24 N1 C1 120.9(2) . . ? N1 C24 N3 122.28(19) . . ? N1 C24 N2 123.19(19) . . ? N3 C24 N2 114.39(18) . . ? N4 C23 N2 116.2(2) . . ? N4 C23 S1 123.97(18) . . ? N2 C23 S1 119.82(15) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 28.20 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.466 _refine_diff_density_min -0.605 _refine_diff_density_rms 0.080 #--------------------------------------------- data_2e _database_code_depnum_ccdc_archive 'CCDC 754860' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 Cl N4 O2 S' _chemical_formula_weight 459.00 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.083(3) _cell_length_b 11.470(4) _cell_length_c 13.401(4) _cell_angle_alpha 66.049(5) _cell_angle_beta 83.186(5) _cell_angle_gamma 67.231(5) _cell_volume 1175.2(6) _cell_formula_units_Z 2 _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 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 1.297 _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.278 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.890 _exptl_absorpt_correction_T_max 0.920 _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 5559 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.31 _reflns_number_total 4785 _reflns_number_gt 2683 _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^)+(0.0850P)^2^+0.3500P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2889 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1234 _refine_ls_wR_factor_gt 0.1149 _refine_ls_goodness_of_fit_ref 0.851 _refine_ls_restrained_S_all 0.851 _refine_ls_shift/su_max 0.013 _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 0.28152(9) 0.68364(8) -0.00170(6) 0.0508(3) Uani 1 1 d . . . Cl2 Cl -0.10238(10) 0.48696(9) 0.39301(7) 0.0764(4) Uani 1 1 d . . . C22 C 0.1255(4) 0.4899(3) 0.1665(2) 0.0353(9) Uani 1 1 d . . . C21 C 0.2822(3) 0.6314(3) 0.1341(2) 0.0394(9) Uani 1 1 d . . . N4 N 0.3114(3) 0.6928(2) 0.1900(2) 0.0453(8) Uani 1 1 d . . . O1 O 0.4569(3) 0.7722(3) 0.3137(2) 0.0820(8) Uani 1 1 d . . . C20 C 0.2752(4) 0.6693(3) 0.3053(2) 0.0531(10) Uani 1 1 d . . . H3A H 0.2529 0.5858 0.3401 0.064 Uiso 1 1 calc R . . H3B H 0.1811 0.7453 0.3088 0.064 Uiso 1 1 calc R . . C19 C 0.4139(5) 0.6567(4) 0.3644(3) 0.0725(12) Uani 1 1 d . . . H4A H 0.3864 0.6460 0.4390 0.087 Uiso 1 1 calc R . . H4B H 0.5046 0.5750 0.3670 0.087 Uiso 1 1 calc R . . C17 C 0.3635(4) 0.8093(3) 0.1380(3) 0.0610(12) Uani 1 1 d . . . H6A H 0.2751 0.8941 0.1315 0.073 Uiso 1 1 calc R . . H6B H 0.3982 0.8164 0.0652 0.073 Uiso 1 1 calc R . . C18 C 0.4983(5) 0.7884(4) 0.2057(4) 0.0753(12) Uani 1 1 d . . . H5A H 0.5889 0.7074 0.2068 0.090 Uiso 1 1 calc R . . H5B H 0.5305 0.8668 0.1722 0.090 Uiso 1 1 calc R . . N3 N 0.1631(3) 0.3737(2) 0.14806(19) 0.0413(7) Uani 1 1 d . . . O2 O 0.2388(4) 0.1234(2) 0.1280(2) 0.0839(9) Uani 1 1 d . . . C16 C 0.0359(4) 0.3303(3) 0.1389(3) 0.0522(9) Uani 1 1 d . . . H7A H -0.0012 0.3694 0.0631 0.063 Uiso 1 1 calc R . . H7B H -0.0535 0.3622 0.1809 0.063 Uiso 1 1 calc R . . C15 C 0.1000(5) 0.1768(3) 0.1812(3) 0.0707(11) Uani 1 1 d . . . H8A H 0.1255 0.1392 0.2589 0.085 Uiso 1 1 calc R . . H8B H 0.0180 0.1475 0.1711 0.085 Uiso 1 1 calc R . . C13 C 0.3059(4) 0.3194(3) 0.0927(2) 0.0522(9) Uani 1 1 d . . . H9A H 0.3895 0.3468 0.1032 0.063 Uiso 1 1 calc R . . H9B H 0.2813 0.3558 0.0149 0.063 Uiso 1 1 calc R . . C14 C 0.3614(5) 0.1658(3) 0.1394(3) 0.0726(13) Uani 1 1 d . . . H10A H 0.4545 0.1288 0.1020 0.087 Uiso 1 1 calc R . . H10B H 0.3922 0.1297 0.2162 0.087 Uiso 1 1 calc R . . N1 N -0.0202(3) 0.5721(2) 0.15842(17) 0.0418(7) Uani 1 1 d . . . N2 N 0.2555(3) 0.5086(2) 0.19894(18) 0.0350(7) Uani 1 1 d . . . C8 C 0.5396(3) 0.3800(3) 0.2523(2) 0.0489(9) Uani 1 1 d . . . H16 H 0.5655 0.4404 0.1885 0.059 Uiso 1 1 calc R . . C12 C 0.3462(3) 0.3033(3) 0.3672(2) 0.0475(9) Uani 1 1 d . . . H12 H 0.2405 0.3122 0.3816 0.057 Uiso 1 1 calc R . . C7 C 0.3807(3) 0.3963(3) 0.2731(2) 0.0346(8) Uani 1 1 d . . . C11 C 0.4673(4) 0.1973(3) 0.4400(2) 0.0597(10) Uani 1 1 d . . . H13 H 0.4416 0.1353 0.5028 0.072 Uiso 1 1 calc R . . C9 C 0.6587(3) 0.2734(3) 0.3274(3) 0.0592(10) Uani 1 1 d . . . H15 H 0.7644 0.2641 0.3130 0.071 Uiso 1 1 calc R . . C10 C 0.6266(3) 0.1804(3) 0.4224(2) 0.0557(10) Uani 1 1 d . . . C23 C 0.7581(4) 0.0666(4) 0.5047(3) 0.0899(14) Uani 1 1 d . . . H17A H 0.8517 0.0893 0.4931 0.135 Uiso 1 1 calc R . . H17B H 0.7827 -0.0179 0.4961 0.135 Uiso 1 1 calc R . . H17C H 0.7233 0.0563 0.5773 0.135 Uiso 1 1 calc R . . C1 C -0.0666(3) 0.6759(3) 0.1991(2) 0.0406(8) Uani 1 1 d . . . C2 C -0.0883(3) 0.8106(3) 0.1313(3) 0.0532(9) Uani 1 1 d . . . H19 H -0.0638 0.8315 0.0582 0.064 Uiso 1 1 calc R . . C6 C -0.1111(3) 0.6508(3) 0.3068(2) 0.0518(9) Uani 1 1 d . . . C5 C -0.1687(4) 0.7553(4) 0.3451(3) 0.0691(11) Uani 1 1 d . . . H22 H -0.1961 0.7360 0.4176 0.083 Uiso 1 1 calc R . . C4 C -0.1849(4) 0.8851(4) 0.2771(3) 0.0777(12) Uani 1 1 d . . . H21 H -0.2229 0.9547 0.3033 0.093 Uiso 1 1 calc R . . C3 C -0.1454(4) 0.9151(3) 0.1694(3) 0.0682(11) Uani 1 1 d . . . H20 H -0.1570 1.0046 0.1228 0.082 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 0.0607(5) 0.0620(5) 0.0371(4) -0.0191(3) 0.0051(4) -0.0318(4) Cl2 0.0724(6) 0.0842(6) 0.0539(5) -0.0158(4) 0.0117(4) -0.0248(5) C22 0.0431(18) 0.0444(15) 0.0253(14) -0.0143(11) 0.0010(14) -0.0228(14) C21 0.0333(16) 0.0473(15) 0.0421(16) -0.0192(14) 0.0010(14) -0.0179(13) N4 0.0544(16) 0.0519(13) 0.0434(14) -0.0240(12) 0.0006(13) -0.0277(12) O1 0.099(2) 0.100(2) 0.0802(19) -0.0459(16) -0.0100(16) -0.0563(17) C20 0.057(2) 0.0647(19) 0.0496(18) -0.0329(16) 0.0002(18) -0.0233(16) C19 0.081(3) 0.087(3) 0.061(2) -0.035(2) -0.005(2) -0.034(2) C17 0.072(3) 0.0557(19) 0.066(2) -0.0234(17) -0.002(2) -0.0345(18) C18 0.074(3) 0.086(3) 0.089(3) -0.034(2) -0.008(3) -0.050(2) N3 0.0442(15) 0.0523(13) 0.0452(14) -0.0286(11) -0.0002(12) -0.0253(12) O2 0.107(2) 0.0559(14) 0.099(2) -0.0408(14) -0.0115(19) -0.0251(15) C16 0.062(2) 0.0571(18) 0.0504(19) -0.0204(15) -0.0093(17) -0.0323(16) C15 0.089(3) 0.060(2) 0.072(2) -0.0166(18) -0.015(2) -0.041(2) C13 0.0597(19) 0.0580(17) 0.0483(17) -0.0329(15) 0.0066(16) -0.0197(15) C14 0.078(3) 0.065(2) 0.079(3) -0.040(2) 0.001(2) -0.020(2) N1 0.0373(13) 0.0539(13) 0.0412(13) -0.0235(11) -0.0014(11) -0.0180(11) N2 0.0348(14) 0.0421(12) 0.0376(13) -0.0183(10) -0.0036(12) -0.0195(10) C8 0.0394(16) 0.0576(17) 0.0520(17) -0.0210(15) 0.0027(15) -0.0211(14) C12 0.0385(16) 0.0615(17) 0.0386(15) -0.0168(14) 0.0037(14) -0.0184(14) C7 0.0329(15) 0.0467(14) 0.0343(14) -0.0221(12) -0.0045(13) -0.0166(12) C11 0.059(2) 0.0663(19) 0.0371(16) -0.0111(15) -0.0004(15) -0.0157(16) C9 0.0313(16) 0.071(2) 0.072(2) -0.0288(18) -0.0010(16) -0.0128(15) C10 0.0442(18) 0.0666(19) 0.0488(18) -0.0240(15) -0.0078(15) -0.0089(15) C23 0.062(2) 0.091(3) 0.081(3) -0.020(2) -0.022(2) 0.000(2) C1 0.0283(15) 0.0562(16) 0.0451(16) -0.0264(14) -0.0039(13) -0.0151(13) C2 0.0477(18) 0.0584(18) 0.0544(18) -0.0261(15) -0.0009(15) -0.0158(14) C6 0.0376(16) 0.0690(19) 0.0450(16) -0.0261(15) -0.0022(14) -0.0112(14) C5 0.054(2) 0.095(3) 0.059(2) -0.049(2) 0.0013(17) -0.0076(19) C4 0.066(2) 0.084(3) 0.094(3) -0.063(2) -0.004(2) -0.005(2) C3 0.062(2) 0.059(2) 0.084(3) -0.0355(19) -0.008(2) -0.0136(17) _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 C21 1.669(3) . ? Cl2 C6 1.737(3) . ? C22 N1 1.280(3) . ? C22 N3 1.360(4) . ? C22 N2 1.423(4) . ? C21 N4 1.322(4) . ? C21 N2 1.420(3) . ? N4 C17 1.467(4) . ? N4 C20 1.476(4) . ? O1 C18 1.406(5) . ? O1 C19 1.406(4) . ? C20 C19 1.496(5) . ? C17 C18 1.496(5) . ? N3 C16 1.457(4) . ? N3 C13 1.464(3) . ? O2 C14 1.421(5) . ? O2 C15 1.420(4) . ? C16 C15 1.494(4) . ? C13 C14 1.497(4) . ? N1 C1 1.406(4) . ? N2 C7 1.427(3) . ? C8 C9 1.383(4) . ? C8 C7 1.390(4) . ? C12 C7 1.377(3) . ? C12 C11 1.377(4) . ? C11 C10 1.388(4) . ? C9 C10 1.376(4) . ? C10 C23 1.511(4) . ? C1 C2 1.385(4) . ? C1 C6 1.394(4) . ? C2 C3 1.385(4) . ? C6 C5 1.387(5) . ? C5 C4 1.353(5) . ? C4 C3 1.379(5) . ? 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 C22 N3 120.3(3) . . ? N1 C22 N2 123.8(3) . . ? N3 C22 N2 115.9(2) . . ? N4 C21 N2 114.9(2) . . ? N4 C21 S1 125.4(2) . . ? N2 C21 S1 119.7(3) . . ? C21 N4 C17 122.4(3) . . ? C21 N4 C20 125.9(2) . . ? C17 N4 C20 111.2(3) . . ? C18 O1 C19 109.8(3) . . ? N4 C20 C19 110.1(3) . . ? O1 C19 C20 112.0(3) . . ? N4 C17 C18 109.3(3) . . ? O1 C18 C17 112.5(3) . . ? C22 N3 C16 119.5(2) . . ? C22 N3 C13 123.6(2) . . ? C16 N3 C13 112.1(2) . . ? C14 O2 C15 110.9(3) . . ? N3 C16 C15 108.6(3) . . ? O2 C15 C16 112.6(3) . . ? N3 C13 C14 108.8(2) . . ? O2 C14 C13 110.8(3) . . ? C22 N1 C1 121.3(3) . . ? C21 N2 C22 117.7(2) . . ? C21 N2 C7 118.6(3) . . ? C22 N2 C7 121.5(2) . . ? C9 C8 C7 119.5(3) . . ? C7 C12 C11 120.4(3) . . ? C12 C7 C8 118.9(2) . . ? C12 C7 N2 120.6(2) . . ? C8 C7 N2 120.4(2) . . ? C12 C11 C10 121.9(3) . . ? C10 C9 C8 122.5(3) . . ? C9 C10 C11 116.8(3) . . ? C9 C10 C23 121.7(3) . . ? C11 C10 C23 121.5(3) . . ? C2 C1 C6 117.0(3) . . ? C2 C1 N1 121.6(2) . . ? C6 C1 N1 121.0(3) . . ? C3 C2 C1 121.8(3) . . ? C5 C6 C1 121.3(3) . . ? C5 C6 Cl2 119.3(2) . . ? C1 C6 Cl2 119.3(2) . . ? C4 C5 C6 120.0(3) . . ? C5 C4 C3 120.6(3) . . ? C4 C3 C2 119.3(3) . . ? _diffrn_measured_fraction_theta_max 0.98 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.0 _refine_diff_density_max 0.282 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.049 #-------------------------------------------------- data_10c _database_code_depnum_ccdc_archive 'CCDC 754861' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H47 N6 S3' _chemical_formula_sum 'C39 H47 N6 S3' _chemical_formula_weight 696.01 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 32' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' _cell_length_a 13.2914(10) _cell_length_b 13.2914(10) _cell_length_c 18.1404(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2775.4(4) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1113 _exptl_absorpt_coefficient_mu 0.237 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.945 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25191 _diffrn_reflns_av_R_equivalents 0.1576 _diffrn_reflns_av_sigmaI/netI 0.1353 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 28.41 _reflns_number_total 8763 _reflns_number_gt 4497 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^ > 2\s(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^)+(0.2000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.36(16) _refine_ls_number_reflns 8763 _refine_ls_number_parameters 405 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2032 _refine_ls_R_factor_gt 0.1343 _refine_ls_wR_factor_ref 0.3631 _refine_ls_wR_factor_gt 0.3239 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 S10 S 0.4785(2) 0.7150(2) 0.26545(12) 0.0651(7) Uani 1 1 d . . . N16 N 0.4844(6) 0.7200(6) 0.1190(3) 0.0498(16) Uani 1 1 d . . . N17 N 0.6453(6) 0.8774(6) 0.1773(4) 0.0581(18) Uani 1 1 d . . . C80 C 0.3882(7) 0.6164(7) 0.1419(4) 0.0451(17) Uani 1 1 d . . . C81 C 0.3665(7) 0.5994(8) 0.2179(4) 0.0501(19) Uani 1 1 d . . . C82 C 0.2744(8) 0.5015(7) 0.2468(5) 0.055(2) Uani 1 1 d . . . H82 H 0.2672 0.4906 0.2976 0.066 Uiso 1 1 calc R . . C83 C 0.1927(8) 0.4191(8) 0.2007(5) 0.058(2) Uani 1 1 d . . . C85 C 0.0863(8) 0.3105(9) 0.2354(6) 0.076(3) Uani 1 1 d . . . H85A H 0.1057 0.2509 0.2437 0.114 Uiso 1 1 calc R . . H85B H 0.0213 0.2821 0.2025 0.114 Uiso 1 1 calc R . . H85C H 0.0667 0.3319 0.2815 0.114 Uiso 1 1 calc R . . C86 C 0.5424(7) 0.7783(6) 0.1805(4) 0.0468(19) Uani 1 1 d . . . C87 C 0.7010(8) 0.9347(7) 0.1083(5) 0.059(2) Uani 1 1 d . . . H87A H 0.6494 0.9503 0.0787 0.071 Uiso 1 1 calc R . . H87B H 0.7234 0.8873 0.0798 0.071 Uiso 1 1 calc R . . C88 C 0.7087(9) 0.9451(7) 0.2392(5) 0.067(3) Uani 1 1 d . . . H88A H 0.7297 0.9000 0.2711 0.081 Uiso 1 1 calc R . . H88B H 0.6614 0.9682 0.2673 0.081 Uiso 1 1 calc R . . C89 C 0.8074(9) 1.0475(10) 0.1324(5) 0.079(3) Uani 1 1 d . . . H89A H 0.8768 1.0528 0.1110 0.095 Uiso 1 1 calc R . . H89B H 0.8011 1.1133 0.1151 0.095 Uiso 1 1 calc R . . C117 C 0.8159(5) 1.0505(5) 0.2120(3) 0.100(4) Uani 1 1 d . . . H11M H 0.8823 1.0395 0.2261 0.120 Uiso 1 1 d R . . H11N H 0.8307 1.1225 0.2359 0.120 Uiso 1 1 d R . . C123 C 0.2077(5) 0.4307(5) 0.1214(3) 0.0502(19) Uani 1 1 d R . . C124 C 0.2960(5) 0.5214(5) 0.0948(3) 0.056(2) Uani 1 1 d R . . H124 H 0.3036 0.5290 0.0439 0.067 Uiso 1 1 calc R . . C125 C 0.1172(2) 0.34055(18) 0.07279(11) 0.070(3) Uani 1 1 d . . . H11F H 0.0578 0.3564 0.0607 0.084 Uiso 1 1 d R . . H11G H 0.0841 0.2646 0.0956 0.084 Uiso 1 1 d R . . H11H H 0.1558 0.3377 0.0279 0.084 Uiso 1 1 d R . . S15 S 0.8202(2) 0.38824(18) 0.26160(11) 0.0677(7) Uani 1 1 d R . . N10 N 0.8239(2) 0.38794(18) 0.11794(11) 0.0479(16) Uani 1 1 d R . . N11 N 0.9788(2) 0.54045(18) 0.17533(11) 0.063(2) Uani 1 1 d R . . C41 C 1.0398(2) 0.60258(18) 0.10035(11) 0.061(2) Uani 1 1 d R . . H41A H 0.9857 0.6096 0.0678 0.073 Uiso 1 1 calc R . . H41B H 1.0716 0.5603 0.0751 0.073 Uiso 1 1 calc R . . C42 C 1.0450(8) 0.6112(8) 0.2365(6) 0.068(3) Uani 1 1 d . . . H42A H 1.0653 0.5666 0.2694 0.081 Uiso 1 1 calc R . . H42B H 0.9992 0.6369 0.2640 0.081 Uiso 1 1 calc R . . C43 C 1.1497(11) 0.7111(8) 0.2086(6) 0.091(4) Uani 1 1 d . . . H43 H 1.2140 0.7584 0.2376 0.109 Uiso 1 1 calc R . . C44 C 0.8841(6) 0.4485(6) 0.1760(4) 0.0422(17) Uani 1 1 d . . . C45 C 0.7252(6) 0.2899(6) 0.1398(4) 0.0452(17) Uani 1 1 d . . . C46 C 0.7037(9) 0.2709(8) 0.2163(5) 0.062(2) Uani 1 1 d . . . C47 C 0.6406(5) 0.2030(5) 0.0890(4) 0.060(2) Uani 1 1 d . . . H47 H 0.6502 0.2113 0.0381 0.072 Uiso 1 1 calc R . . C48 C 0.6027(5) 0.1740(5) 0.2454(4) 0.064(3) Uani 1 1 d R . . H48 H 0.5895 0.1685 0.2960 0.077 Uiso 1 1 calc R . . C49 C 0.5269(7) 0.0914(7) 0.2012(4) 0.0480(18) Uani 1 1 d . . . C50 C 0.5457(7) 0.1077(7) 0.1205(4) 0.0482(19) Uani 1 1 d . . . C51 C 0.4529(9) 0.0088(8) 0.0736(5) 0.074(3) Uani 1 1 d . . . H51A H 0.3895 0.0226 0.0649 0.110 Uiso 1 1 calc R . . H51B H 0.4249 -0.0636 0.0992 0.110 Uiso 1 1 calc R . . H51C H 0.4861 0.0055 0.0273 0.110 Uiso 1 1 calc R . . C52 C 0.4217(8) -0.0140(7) 0.2273(6) 0.065(2) Uani 1 1 d . . . H52A H 0.4333 -0.0796 0.2237 0.098 Uiso 1 1 calc R . . H52B H 0.3565 -0.0275 0.1973 0.098 Uiso 1 1 calc R . . H52C H 0.4067 -0.0036 0.2777 0.098 Uiso 1 1 calc R . . C78 C 1.14213(17) 0.72923(18) 0.12727(10) 0.117(5) Uani 1 1 d . . . H78A H 1.2129 0.7477 0.1049 0.141 Uiso 1 1 d R . . H78B H 1.1234 0.7908 0.1160 0.141 Uiso 1 1 d R . . S16 S -0.05000(17) 0.85359(18) 0.06763(10) 0.0580(6) Uani 1 1 d R . . C01 C -0.11124(17) 0.79165(18) 0.15824(10) 0.0436(18) Uani 1 1 d R . . N12 N -0.20797(17) 0.68853(18) 0.15667(10) 0.0561(18) Uani 1 1 d R . . C53 C 0.16292(17) 1.06173(18) 0.08298(10) 0.0473(18) Uani 1 1 d R . . H53 H 0.1721 1.0709 0.0322 0.057 Uiso 1 1 calc R . . C54 C 0.0653(6) 0.9663(6) 0.1131(3) 0.0427(17) Uani 1 1 d . . . C55 C 0.0512(7) 0.9470(6) 0.1899(3) 0.0406(17) Uani 1 1 d . . . C56 C 0.1392(7) 1.0311(7) 0.2333(4) 0.0454(18) Uani 1 1 d . . . H56 H 0.1316 1.0211 0.2841 0.054 Uiso 1 1 calc R . . C57 C 0.2347(7) 1.1260(7) 0.2078(5) 0.050(2) Uani 1 1 d . . . C58 C 0.3232(8) 1.2122(9) 0.2605(6) 0.079(3) Uani 1 1 d . . . H58A H 0.2918 1.2546 0.2847 0.119 Uiso 1 1 calc R . . H58B H 0.3920 1.2652 0.2338 0.119 Uiso 1 1 calc R . . H58C H 0.3425 1.1717 0.2967 0.119 Uiso 1 1 calc R . . C59 C 0.2445(7) 1.1413(7) 0.1293(4) 0.0487(19) Uani 1 1 d . . . C60 C 0.3521(9) 1.2509(9) 0.0996(6) 0.078(3) Uani 1 1 d . . . H60A H 0.3409 1.2607 0.0484 0.116 Uiso 1 1 calc R . . H60B H 0.4194 1.2427 0.1052 0.116 Uiso 1 1 calc R . . H60C H 0.3630 1.3176 0.1268 0.116 Uiso 1 1 calc R . . C61 C -0.2633(7) 0.6327(7) 0.2264(5) 0.058(2) Uani 1 1 d . . . H61A H -0.2786 0.6836 0.2568 0.069 Uiso 1 1 calc R . . H61B H -0.2160 0.6090 0.2539 0.069 Uiso 1 1 calc R . . C63 C -0.2742(8) 0.6286(8) 0.0913(5) 0.071(3) Uani 1 1 d . . . H63A H -0.2280 0.6100 0.0586 0.085 Uiso 1 1 calc R . . H63B H -0.2981 0.6765 0.0648 0.085 Uiso 1 1 calc R . . N01 N -0.0502(5) 0.8465(5) 0.2128(3) 0.0438(15) Uani 1 1 d . . . C116 C -0.3752(9) 0.5285(9) 0.1998(5) 0.070(3) Uani 1 1 d . . . H11I H -0.3822 0.4580 0.2204 0.084 Uiso 1 1 calc R . . H11J H -0.4410 0.5351 0.2164 0.084 Uiso 1 1 calc R . . C126 C -0.3756(9) 0.5224(12) 0.1182(6) 0.103(5) Uani 1 1 d . . . H12I H -0.3716 0.4547 0.1024 0.123 Uiso 1 1 calc R . . H12J H -0.4463 0.5164 0.0987 0.123 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 S10 0.0831(17) 0.0594(14) 0.0411(11) 0.0004(10) -0.0066(10) 0.0269(13) N16 0.056(4) 0.046(4) 0.035(3) -0.011(3) -0.013(3) 0.016(3) N17 0.060(4) 0.049(4) 0.041(4) -0.001(3) 0.001(3) 0.009(3) C80 0.047(4) 0.052(4) 0.035(4) -0.002(3) -0.005(3) 0.025(4) C81 0.050(5) 0.058(5) 0.045(4) -0.002(4) -0.013(3) 0.030(4) C82 0.058(5) 0.057(5) 0.046(5) 0.010(4) -0.001(4) 0.025(4) C83 0.057(5) 0.061(5) 0.056(5) -0.005(4) -0.013(4) 0.029(4) C85 0.050(5) 0.061(6) 0.095(8) 0.014(5) 0.000(5) 0.012(5) C86 0.056(5) 0.038(4) 0.041(4) -0.015(3) -0.018(3) 0.019(4) C87 0.074(6) 0.057(5) 0.045(4) -0.013(4) 0.006(4) 0.031(5) C88 0.089(7) 0.046(5) 0.049(5) -0.001(4) -0.019(5) 0.021(5) C89 0.075(6) 0.090(7) 0.057(6) -0.004(5) -0.022(5) 0.029(6) C117 0.087(8) 0.083(8) 0.069(7) -0.003(6) -0.002(6) -0.003(6) C123 0.050(4) 0.068(5) 0.042(4) 0.009(4) 0.000(4) 0.036(4) C124 0.084(6) 0.062(5) 0.031(4) 0.006(4) 0.015(4) 0.042(5) C125 0.081(7) 0.083(7) 0.044(5) 0.000(5) -0.008(5) 0.040(6) S15 0.0791(17) 0.0567(14) 0.0476(13) -0.0039(10) -0.0065(11) 0.0192(13) N10 0.042(3) 0.046(4) 0.037(3) 0.000(3) 0.001(3) 0.008(3) N11 0.049(4) 0.065(5) 0.052(4) -0.007(3) -0.002(3) 0.010(4) C41 0.058(5) 0.048(5) 0.061(5) -0.001(4) 0.008(4) 0.014(4) C42 0.053(5) 0.062(6) 0.068(6) -0.015(5) -0.015(4) 0.013(5) C43 0.100(8) 0.047(5) 0.066(6) 0.006(5) -0.016(6) -0.009(5) C44 0.043(4) 0.036(4) 0.035(4) 0.005(3) -0.003(3) 0.010(3) C45 0.039(4) 0.039(4) 0.051(4) -0.010(3) -0.014(3) 0.014(3) C46 0.088(7) 0.066(6) 0.057(5) -0.011(4) -0.018(5) 0.056(6) C47 0.034(4) 0.030(4) 0.101(7) -0.018(4) 0.010(4) 0.004(3) C48 0.085(7) 0.079(7) 0.049(5) 0.022(5) 0.020(5) 0.057(6) C49 0.052(5) 0.044(4) 0.043(4) 0.009(3) 0.005(4) 0.020(4) C50 0.040(4) 0.063(5) 0.034(4) 0.003(3) 0.005(3) 0.021(4) C51 0.073(7) 0.055(5) 0.062(6) 0.007(4) -0.016(5) 0.009(5) C52 0.052(5) 0.045(5) 0.081(6) 0.017(4) 0.013(5) 0.011(4) C78 0.074(8) 0.101(10) 0.098(9) -0.001(8) -0.015(7) -0.015(7) S16 0.0526(12) 0.0680(14) 0.0359(9) -0.0036(9) -0.0020(8) 0.0169(11) C01 0.025(3) 0.034(4) 0.061(5) 0.007(3) -0.002(3) 0.007(3) N12 0.045(4) 0.057(4) 0.041(3) -0.010(3) 0.001(3) 0.006(3) C53 0.047(4) 0.044(4) 0.043(4) 0.008(3) 0.014(3) 0.017(4) C54 0.048(4) 0.035(4) 0.027(3) 0.005(3) 0.013(3) 0.008(3) C55 0.059(5) 0.047(4) 0.023(3) 0.011(3) 0.014(3) 0.032(4) C56 0.059(5) 0.061(5) 0.025(3) -0.016(3) -0.007(3) 0.037(4) C57 0.050(5) 0.041(4) 0.052(5) -0.017(4) -0.003(4) 0.019(4) C58 0.044(5) 0.070(6) 0.089(7) -0.045(6) -0.012(5) 0.002(4) C59 0.051(5) 0.043(4) 0.046(4) 0.005(3) 0.012(4) 0.019(4) C60 0.069(6) 0.084(7) 0.084(7) 0.020(6) 0.016(5) 0.042(6) C61 0.051(5) 0.038(4) 0.069(6) 0.004(4) 0.003(4) 0.010(4) C63 0.051(5) 0.070(6) 0.060(5) -0.021(5) -0.024(4) 0.006(5) N01 0.039(3) 0.048(4) 0.035(3) 0.005(3) 0.012(3) 0.015(3) C116 0.072(6) 0.067(6) 0.053(5) 0.007(4) -0.002(4) 0.021(5) C126 0.057(6) 0.126(10) 0.054(6) -0.032(6) -0.002(5) -0.006(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 S10 C81 1.741(9) . ? S10 C86 1.758(9) . ? N16 C86 1.358(9) . ? N16 C80 1.394(10) . ? N17 C86 1.344(10) . ? N17 C88 1.423(10) . ? N17 C87 1.460(11) . ? C80 C81 1.403(11) . ? C80 C124 1.509(9) . ? C81 C82 1.369(12) . ? C82 C83 1.375(12) . ? C82 H82 0.9300 . ? C83 C123 1.450(10) . ? C83 C85 1.562(13) . ? C85 H85A 0.9600 . ? C85 H85B 0.9600 . ? C85 H85C 0.9600 . ? C87 C89 1.523(13) . ? C87 H87A 0.9700 . ? C87 H87B 0.9700 . ? C88 C117 1.496(11) . ? C88 H88A 0.9700 . ? C88 H88B 0.9700 . ? C89 C117 1.448(11) . ? C89 H89A 0.9700 . ? C89 H89B 0.9700 . ? C117 H11M 0.9980 . ? C117 H11N 0.9773 . ? C123 C124 1.2837 . ? C123 C125 1.489(6) . ? C124 H124 0.9300 . ? C125 H11F 0.9392 . ? C125 H11G 0.9697 . ? C125 H11H 0.9739 . ? S15 C46 1.758(10) . ? S15 C44 1.759(8) . ? N10 C44 1.325(7) . ? N10 C45 1.366(8) . ? N11 C44 1.240(7) . ? N11 C42 1.437(9) . ? N11 C41 1.5876 . ? C41 C78 1.623(3) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 C43 1.452(14) . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C43 C78 1.506(11) . ? C43 H43 0.9300 . ? C45 C46 1.415(12) . ? C45 C47 1.466(9) . ? C46 C48 1.418(12) . ? C47 C50 1.388(10) . ? C47 H47 0.9300 . ? C48 C49 1.325(10) . ? C48 H48 0.9300 . ? C49 C50 1.484(11) . ? C49 C52 1.477(11) . ? C50 C51 1.533(12) . ? C51 H51A 0.9600 . ? C51 H51B 0.9600 . ? C51 H51C 0.9600 . ? C52 H52A 0.9600 . ? C52 H52B 0.9600 . ? C52 H52C 0.9600 . ? C78 H78A 0.9378 . ? C78 H78B 0.9892 . ? S16 C54 1.726(7) . ? S16 C01 1.8361 . ? C01 N01 1.257(7) . ? C01 N12 1.3305 . ? N12 C63 1.454(8) . ? N12 C61 1.465(9) . ? C53 C59 1.362(9) . ? C53 C54 1.394(7) . ? C53 H53 0.9300 . ? C54 C55 1.413(9) . ? C55 C56 1.389(11) . ? C55 N01 1.404(9) . ? C56 C57 1.347(11) . ? C56 H56 0.9300 . ? C57 C59 1.435(12) . ? C57 C58 1.504(11) . ? C58 H58A 0.9600 . ? C58 H58B 0.9600 . ? C58 H58C 0.9600 . ? C59 C60 1.541(13) . ? C60 H60A 0.9600 . ? C60 H60B 0.9600 . ? C60 H60C 0.9600 . ? C61 C116 1.518(12) . ? C61 H61A 0.9700 . ? C61 H61B 0.9700 . ? C63 C126 1.465(14) . ? C63 H63A 0.9700 . ? C63 H63B 0.9700 . ? C116 C126 1.482(13) . ? C116 H11I 0.9700 . ? C116 H11J 0.9700 . ? C126 H12I 0.9700 . ? C126 H12J 0.9700 . ? 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 C81 S10 C86 89.1(4) . . ? C86 N16 C80 107.3(7) . . ? C86 N17 C88 125.2(7) . . ? C86 N17 C87 123.4(7) . . ? C88 N17 C87 111.2(7) . . ? N16 C80 C81 117.8(7) . . ? N16 C80 C124 128.1(6) . . ? C81 C80 C124 113.9(6) . . ? C82 C81 C80 122.9(8) . . ? C82 C81 S10 127.8(6) . . ? C80 C81 S10 109.2(6) . . ? C81 C82 C83 119.9(8) . . ? C81 C82 H82 120.1 . . ? C83 C82 H82 120.1 . . ? C82 C83 C123 120.5(8) . . ? C82 C83 C85 118.6(8) . . ? C123 C83 C85 120.8(7) . . ? C83 C85 H85A 109.5 . . ? C83 C85 H85B 109.5 . . ? H85A C85 H85B 109.5 . . ? C83 C85 H85C 109.5 . . ? H85A C85 H85C 109.5 . . ? H85B C85 H85C 109.5 . . ? N17 C86 N16 122.2(8) . . ? N17 C86 S10 121.3(6) . . ? N16 C86 S10 116.5(6) . . ? N17 C87 C89 104.3(7) . . ? N17 C87 H87A 110.9 . . ? C89 C87 H87A 110.9 . . ? N17 C87 H87B 110.9 . . ? C89 C87 H87B 110.9 . . ? H87A C87 H87B 108.9 . . ? N17 C88 C117 108.5(7) . . ? N17 C88 H88A 110.0 . . ? C117 C88 H88A 110.0 . . ? N17 C88 H88B 110.0 . . ? C117 C88 H88B 110.0 . . ? H88A C88 H88B 108.4 . . ? C117 C89 C87 109.5(8) . . ? C117 C89 H89A 109.8 . . ? C87 C89 H89A 109.8 . . ? C117 C89 H89B 109.8 . . ? C87 C89 H89B 109.8 . . ? H89A C89 H89B 108.2 . . ? C89 C117 C88 106.2(6) . . ? C89 C117 H11M 108.3 . . ? C88 C117 H11M 106.1 . . ? C89 C117 H11N 116.3 . . ? C88 C117 H11N 113.7 . . ? H11M C117 H11N 105.6 . . ? C124 C123 C83 119.0(4) . . ? C124 C123 C125 121.7(2) . . ? C83 C123 C125 119.3(5) . . ? C123 C124 C80 123.5(3) . . ? C123 C124 H124 118.2 . . ? C80 C124 H124 118.2 . . ? C123 C125 H11F 112.9 . . ? C123 C125 H11G 110.4 . . ? H11F C125 H11G 109.8 . . ? C123 C125 H11H 107.3 . . ? H11F C125 H11H 109.4 . . ? H11G C125 H11H 106.9 . . ? C46 S15 C44 90.1(4) . . ? C44 N10 C45 110.5(5) . . ? C44 N11 C42 128.7(5) . . ? C44 N11 C41 121.6(3) . . ? C42 N11 C41 109.6(4) . . ? N11 C41 C78 103.12(10) . . ? N11 C41 H41A 111.1 . . ? C78 C41 H41A 111.1 . . ? N11 C41 H41B 111.1 . . ? C78 C41 H41B 111.1 . . ? H41A C41 H41B 109.1 . . ? N11 C42 C43 108.8(8) . . ? N11 C42 H42A 109.9 . . ? C43 C42 H42A 109.9 . . ? N11 C42 H42B 109.9 . . ? C43 C42 H42B 109.9 . . ? H42A C42 H42B 108.3 . . ? C42 C43 C78 112.2(8) . . ? C42 C43 H43 123.9 . . ? C78 C43 H43 123.9 . . ? N11 C44 N10 126.7(6) . . ? N11 C44 S15 118.6(5) . . ? N10 C44 S15 114.7(5) . . ? N10 C45 C46 117.8(6) . . ? N10 C45 C47 124.2(6) . . ? C46 C45 C47 118.0(7) . . ? C45 C46 C48 122.9(8) . . ? C45 C46 S15 106.9(7) . . ? C48 C46 S15 130.2(7) . . ? C50 C47 C45 116.8(7) . . ? C50 C47 H47 121.6 . . ? C45 C47 H47 121.6 . . ? C49 C48 C46 120.7(7) . . ? C49 C48 H48 119.7 . . ? C46 C48 H48 119.7 . . ? C48 C49 C50 118.2(7) . . ? C48 C49 C52 124.0(8) . . ? C50 C49 C52 117.7(8) . . ? C47 C50 C49 123.3(7) . . ? C47 C50 C51 121.9(7) . . ? C49 C50 C51 114.7(7) . . ? C50 C51 H51A 109.5 . . ? C50 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C50 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C49 C52 H52A 109.5 . . ? C49 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C49 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C43 C78 C41 102.5(4) . . ? C43 C78 H78A 109.1 . . ? C41 C78 H78A 110.6 . . ? C43 C78 H78B 113.6 . . ? C41 C78 H78B 111.6 . . ? H78A C78 H78B 109.2 . . ? C54 S16 C01 87.9(2) . . ? N01 C01 N12 128.7(3) . . ? N01 C01 S16 115.6(3) . . ? N12 C01 S16 115.2 . . ? C01 N12 C63 126.2(4) . . ? C01 N12 C61 119.0(3) . . ? C63 N12 C61 114.4(5) . . ? C59 C53 C54 118.8(4) . . ? C59 C53 H53 120.6 . . ? C54 C53 H53 120.6 . . ? C53 C54 C55 122.0(6) . . ? C53 C54 S16 128.4(4) . . ? C55 C54 S16 109.5(5) . . ? C56 C55 N01 128.3(6) . . ? C56 C55 C54 115.5(7) . . ? N01 C55 C54 116.2(7) . . ? C57 C56 C55 125.4(7) . . ? C57 C56 H56 117.3 . . ? C55 C56 H56 117.3 . . ? C56 C57 C59 116.7(7) . . ? C56 C57 C58 120.5(8) . . ? C59 C57 C58 122.8(8) . . ? C57 C58 H58A 109.5 . . ? C57 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C57 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C53 C59 C57 121.5(6) . . ? C53 C59 C60 121.4(7) . . ? C57 C59 C60 117.2(8) . . ? C59 C60 H60A 109.5 . . ? C59 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? C59 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? N12 C61 C116 101.6(7) . . ? N12 C61 H61A 111.4 . . ? C116 C61 H61A 111.4 . . ? N12 C61 H61B 111.4 . . ? C116 C61 H61B 111.4 . . ? H61A C61 H61B 109.3 . . ? N12 C63 C126 105.7(7) . . ? N12 C63 H63A 110.6 . . ? C126 C63 H63A 110.6 . . ? N12 C63 H63B 110.6 . . ? C126 C63 H63B 110.6 . . ? H63A C63 H63B 108.7 . . ? C01 N01 C55 110.7(5) . . ? C126 C116 C61 110.1(8) . . ? C126 C116 H11I 109.6 . . ? C61 C116 H11I 109.6 . . ? C126 C116 H11J 109.6 . . ? C61 C116 H11J 109.6 . . ? H11I C116 H11J 108.2 . . ? C63 C126 C116 107.6(8) . . ? C63 C126 H12I 110.2 . . ? C116 C126 H12I 110.2 . . ? C63 C126 H12J 110.2 . . ? C116 C126 H12J 110.2 . . ? H12I C126 H12J 108.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.951 _refine_diff_density_min -1.080 _refine_diff_density_rms 0.184