# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_d12324 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H30 N3 O2 S, Br' _chemical_formula_sum 'C20 H30 Br N3 O2 S' _chemical_formula_weight 456.44 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' Br Br -0.6763 1.2805 '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' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.7757(5) _cell_length_b 11.5358(5) _cell_length_c 16.1129(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.112(2) _cell_angle_gamma 90.00 _cell_volume 2183.18(16) _cell_formula_units_Z 4 _cell_measurement_temperature 147(2) _cell_measurement_reflns_used 9542 _cell_measurement_theta_min 4.72 _cell_measurement_theta_max 66.50 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 3.612 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6384 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 147(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker ImuS' _diffrn_radiation_monochromator 'muliti-layer optics' _diffrn_measurement_device_type 'Bruker Kappa APEX-DUO CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13673 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.72 _diffrn_reflns_theta_max 66.49 _reflns_number_total 3752 _reflns_number_gt 3420 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement APEX2 _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0290P)^2^+1.1104P] 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 3752 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0282 _refine_ls_R_factor_gt 0.0248 _refine_ls_wR_factor_ref 0.0652 _refine_ls_wR_factor_gt 0.0632 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.002 _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 Br1 Br 0.522172(16) 0.189227(17) 0.375833(11) 0.02502(8) Uani 1 1 d . . . S1 S 0.90272(4) 0.20237(4) 0.40811(3) 0.02147(11) Uani 1 1 d . . . O1 O 0.86111(11) 0.27130(12) 0.33828(7) 0.0275(3) Uani 1 1 d . . . O2 O 1.00087(11) 0.13044(12) 0.40168(8) 0.0270(3) Uani 1 1 d . . . N1 N 0.84990(15) 0.61296(15) 0.68079(9) 0.0290(4) Uani 1 1 d . . . N2 N 0.79869(14) 0.12039(14) 0.42986(9) 0.0236(3) Uani 1 1 d . . . N3 N 0.63896(13) 0.12841(13) 0.66971(9) 0.0221(3) Uani 1 1 d . . . C1 C 0.93637(16) 0.29713(15) 0.49368(11) 0.0208(4) Uani 1 1 d . . . C2 C 1.04488(16) 0.29297(16) 0.53020(12) 0.0244(4) Uani 1 1 d . . . H2A H 1.0970 0.2367 0.5127 0.029 Uiso 1 1 calc R . . C3 C 1.07933(17) 0.37188(18) 0.59365(12) 0.0281(4) Uani 1 1 d . . . H3A H 1.1552 0.3698 0.6181 0.034 Uiso 1 1 calc R . . C4 C 1.00420(17) 0.45148(17) 0.62034(11) 0.0256(4) Uani 1 1 d . . . H4A H 1.0292 0.5057 0.6621 0.031 Uiso 1 1 calc R . . C5 C 0.88981(16) 0.45455(16) 0.58684(10) 0.0212(4) Uani 1 1 d . . . C6 C 0.81068(16) 0.53824(16) 0.61545(11) 0.0233(4) Uani 1 1 d . . . C7 C 0.70338(17) 0.54538(17) 0.57615(11) 0.0268(4) Uani 1 1 d . . . H7A H 0.6515 0.6020 0.5934 0.032 Uiso 1 1 calc R . . C8 C 0.66975(16) 0.46959(17) 0.51057(12) 0.0268(4) Uani 1 1 d . . . H8A H 0.5949 0.4755 0.4848 0.032 Uiso 1 1 calc R . . C9 C 0.74177(16) 0.38788(16) 0.48303(11) 0.0229(4) Uani 1 1 d . . . H9A H 0.7167 0.3374 0.4389 0.027 Uiso 1 1 calc R . . C10 C 0.85431(15) 0.37819(16) 0.52034(10) 0.0200(4) Uani 1 1 d . . . C11 C 0.8655(3) 0.5587(2) 0.76250(13) 0.0560(7) Uani 1 1 d . . . H11A H 0.9004 0.4821 0.7571 0.084 Uiso 1 1 calc R . . H11B H 0.7915 0.5501 0.7860 0.084 Uiso 1 1 calc R . . H11C H 0.9153 0.6073 0.7994 0.084 Uiso 1 1 calc R . . C12 C 0.7900(2) 0.72290(19) 0.68543(14) 0.0361(5) Uani 1 1 d . . . H12A H 0.7815 0.7582 0.6300 0.054 Uiso 1 1 calc R . . H12B H 0.8336 0.7750 0.7237 0.054 Uiso 1 1 calc R . . H12C H 0.7146 0.7095 0.7057 0.054 Uiso 1 1 calc R . . C13 C 0.81301(17) 0.02436(17) 0.48865(12) 0.0269(4) Uani 1 1 d . . . H13A H 0.8912 -0.0065 0.4869 0.032 Uiso 1 1 calc R . . H13B H 0.7596 -0.0383 0.4702 0.032 Uiso 1 1 calc R . . C14 C 0.79306(16) 0.05557(17) 0.57855(12) 0.0261(4) Uani 1 1 d . . . H14A H 0.8177 -0.0094 0.6157 0.031 Uiso 1 1 calc R . . H14B H 0.8386 0.1248 0.5957 0.031 Uiso 1 1 calc R . . C15 C 0.66758(15) 0.08019(17) 0.58624(11) 0.0225(4) Uani 1 1 d . . . H15A H 0.6414 0.1361 0.5423 0.027 Uiso 1 1 calc R . . H15B H 0.6244 0.0074 0.5758 0.027 Uiso 1 1 calc R . . C16 C 0.51029(17) 0.12795(18) 0.67346(11) 0.0271(4) Uani 1 1 d . . . H16A H 0.4831 0.0467 0.6705 0.033 Uiso 1 1 calc R . . H16B H 0.4914 0.1600 0.7278 0.033 Uiso 1 1 calc R . . C17 C 0.44809(18) 0.1957(2) 0.60585(13) 0.0364(5) Uani 1 1 d . . . H17A H 0.4515 0.1708 0.5499 0.044 Uiso 1 1 calc R . . C18 C 0.3894(2) 0.2876(3) 0.62083(18) 0.0584(8) Uani 1 1 d . . . H18A H 0.3851 0.3137 0.6764 0.070 Uiso 1 1 calc R . . H18B H 0.3508 0.3288 0.5762 0.070 Uiso 1 1 calc R . . C19 C 0.68698(19) 0.05284(18) 0.73941(12) 0.0317(5) Uani 1 1 d . . . H19A H 0.6592 0.0796 0.7920 0.048 Uiso 1 1 calc R . . H19B H 0.7703 0.0570 0.7426 0.048 Uiso 1 1 calc R . . H19C H 0.6628 -0.0275 0.7291 0.048 Uiso 1 1 calc R . . C20 C 0.68369(18) 0.24960(17) 0.68169(11) 0.0276(4) Uani 1 1 d . . . H20A H 0.6578 0.2817 0.7334 0.041 Uiso 1 1 calc R . . H20B H 0.6553 0.2979 0.6347 0.041 Uiso 1 1 calc R . . H20C H 0.7671 0.2483 0.6848 0.041 Uiso 1 1 calc R . . H2N H 0.735(2) 0.147(2) 0.4135(14) 0.028(6) 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 Br1 0.02368(12) 0.02841(13) 0.02271(12) 0.00159(7) -0.00006(7) -0.00224(8) S1 0.0205(2) 0.0226(2) 0.0214(2) -0.00020(17) 0.00236(16) 0.00261(17) O1 0.0281(7) 0.0331(8) 0.0212(6) 0.0030(5) 0.0010(5) 0.0026(6) O2 0.0236(7) 0.0270(7) 0.0308(7) -0.0020(6) 0.0048(5) 0.0062(6) N1 0.0371(10) 0.0259(9) 0.0237(8) -0.0037(7) 0.0015(7) 0.0039(7) N2 0.0189(8) 0.0234(9) 0.0284(8) -0.0001(6) 0.0009(6) 0.0022(7) N3 0.0265(8) 0.0209(8) 0.0186(7) 0.0006(6) 0.0001(6) -0.0018(6) C1 0.0208(9) 0.0200(9) 0.0217(8) 0.0040(7) 0.0018(7) -0.0003(7) C2 0.0224(10) 0.0233(10) 0.0274(9) 0.0042(7) 0.0011(7) 0.0032(8) C3 0.0233(10) 0.0286(11) 0.0315(10) 0.0034(8) -0.0051(8) 0.0007(8) C4 0.0283(10) 0.0234(10) 0.0243(9) 0.0007(7) -0.0028(7) -0.0021(8) C5 0.0242(9) 0.0200(9) 0.0195(8) 0.0061(7) 0.0019(7) 0.0003(7) C6 0.0290(10) 0.0206(10) 0.0209(8) 0.0032(7) 0.0058(7) -0.0007(8) C7 0.0276(10) 0.0249(10) 0.0289(9) 0.0016(8) 0.0078(8) 0.0059(8) C8 0.0214(10) 0.0278(10) 0.0310(10) 0.0025(8) 0.0006(7) 0.0034(8) C9 0.0222(9) 0.0228(10) 0.0235(9) 0.0009(7) 0.0007(7) 0.0012(7) C10 0.0198(9) 0.0196(9) 0.0207(8) 0.0053(7) 0.0023(7) -0.0007(7) C11 0.094(2) 0.0506(16) 0.0227(11) -0.0012(10) -0.0022(12) 0.0185(15) C12 0.0408(13) 0.0304(11) 0.0378(11) -0.0094(9) 0.0062(9) 0.0036(10) C13 0.0256(10) 0.0202(10) 0.0355(10) 0.0005(8) 0.0061(8) 0.0035(8) C14 0.0229(10) 0.0254(10) 0.0300(10) 0.0045(8) 0.0007(7) 0.0022(8) C15 0.0230(10) 0.0245(10) 0.0200(8) -0.0023(7) 0.0011(7) -0.0004(8) C16 0.0275(10) 0.0291(11) 0.0256(9) -0.0013(8) 0.0079(8) -0.0015(8) C17 0.0265(11) 0.0559(15) 0.0276(10) 0.0031(9) 0.0074(8) 0.0063(10) C18 0.0586(17) 0.0664(19) 0.0530(15) 0.0272(13) 0.0236(13) 0.0277(15) C19 0.0399(12) 0.0306(11) 0.0238(9) 0.0078(8) -0.0034(8) -0.0012(9) C20 0.0369(11) 0.0216(10) 0.0244(9) -0.0019(8) 0.0023(8) -0.0068(8) _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 O2 1.4325(13) . ? S1 O1 1.4350(13) . ? S1 N2 1.6060(16) . ? S1 C1 1.7818(18) . ? N1 C6 1.412(3) . ? N1 C12 1.456(3) . ? N1 C11 1.458(3) . ? N2 C13 1.459(2) . ? N2 H2N 0.84(2) . ? N3 C19 1.500(2) . ? N3 C20 1.501(2) . ? N3 C15 1.516(2) . ? N3 C16 1.521(2) . ? C1 C2 1.369(3) . ? C1 C10 1.433(3) . ? C2 C3 1.407(3) . ? C2 H2A 0.9500 . ? C3 C4 1.366(3) . ? C3 H3A 0.9500 . ? C4 C5 1.415(3) . ? C4 H4A 0.9500 . ? C5 C10 1.426(3) . ? C5 C6 1.440(3) . ? C6 C7 1.375(3) . ? C7 C8 1.406(3) . ? C7 H7A 0.9500 . ? C8 C9 1.363(3) . ? C8 H8A 0.9500 . ? C9 C10 1.420(3) . ? C9 H9A 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.527(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.519(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.490(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.297(3) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C18 H18B 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 O2 S1 O1 119.75(8) . . ? O2 S1 N2 107.86(9) . . ? O1 S1 N2 105.94(8) . . ? O2 S1 C1 105.99(8) . . ? O1 S1 C1 108.13(8) . . ? N2 S1 C1 108.85(8) . . ? C6 N1 C12 115.87(17) . . ? C6 N1 C11 115.12(18) . . ? C12 N1 C11 110.99(17) . . ? C13 N2 S1 122.29(14) . . ? C13 N2 H2N 122.8(16) . . ? S1 N2 H2N 113.5(16) . . ? C19 N3 C20 109.57(15) . . ? C19 N3 C15 110.81(15) . . ? C20 N3 C15 110.95(14) . . ? C19 N3 C16 106.94(14) . . ? C20 N3 C16 109.85(15) . . ? C15 N3 C16 108.64(13) . . ? C2 C1 C10 121.53(17) . . ? C2 C1 S1 117.40(14) . . ? C10 C1 S1 121.01(14) . . ? C1 C2 C3 120.10(18) . . ? C1 C2 H2A 120.0 . . ? C3 C2 H2A 120.0 . . ? C4 C3 C2 120.28(18) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C3 C4 C5 121.14(18) . . ? C3 C4 H4A 119.4 . . ? C5 C4 H4A 119.4 . . ? C4 C5 C10 119.39(16) . . ? C4 C5 C6 120.98(17) . . ? C10 C5 C6 119.53(17) . . ? C7 C6 N1 123.19(17) . . ? C7 C6 C5 119.16(17) . . ? N1 C6 C5 117.59(17) . . ? C6 C7 C8 120.59(17) . . ? C6 C7 H7A 119.7 . . ? C8 C7 H7A 119.7 . . ? C9 C8 C7 121.74(18) . . ? C9 C8 H8A 119.1 . . ? C7 C8 H8A 119.1 . . ? C8 C9 C10 120.01(18) . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C9 C10 C5 118.94(16) . . ? C9 C10 C1 123.61(17) . . ? C5 C10 C1 117.43(16) . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 C14 114.73(16) . . ? N2 C13 H13A 108.6 . . ? C14 C13 H13A 108.6 . . ? N2 C13 H13B 108.6 . . ? C14 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? C15 C14 C13 109.77(15) . . ? C15 C14 H14A 109.7 . . ? C13 C14 H14A 109.7 . . ? C15 C14 H14B 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? N3 C15 C14 114.88(15) . . ? N3 C15 H15A 108.5 . . ? C14 C15 H15A 108.5 . . ? N3 C15 H15B 108.5 . . ? C14 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? C17 C16 N3 114.08(15) . . ? C17 C16 H16A 108.7 . . ? N3 C16 H16A 108.7 . . ? C17 C16 H16B 108.7 . . ? N3 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? C18 C17 C16 122.2(2) . . ? C18 C17 H17A 118.9 . . ? C16 C17 H17A 118.9 . . ? C17 C18 H18A 120.0 . . ? C17 C18 H18B 120.0 . . ? H18A C18 H18B 120.0 . . ? N3 C19 H19A 109.5 . . ? N3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N3 C20 H20A 109.5 . . ? N3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 O2 S1 N2 C13 40.40(16) . . . . ? O1 S1 N2 C13 169.75(14) . . . . ? C1 S1 N2 C13 -74.18(16) . . . . ? O2 S1 C1 C2 5.80(16) . . . . ? O1 S1 C1 C2 -123.77(14) . . . . ? N2 S1 C1 C2 121.58(15) . . . . ? O2 S1 C1 C10 -177.12(14) . . . . ? O1 S1 C1 C10 53.31(16) . . . . ? N2 S1 C1 C10 -61.34(16) . . . . ? C10 C1 C2 C3 -2.1(3) . . . . ? S1 C1 C2 C3 174.97(14) . . . . ? C1 C2 C3 C4 1.3(3) . . . . ? C2 C3 C4 C5 1.8(3) . . . . ? C3 C4 C5 C10 -4.1(3) . . . . ? C3 C4 C5 C6 179.67(17) . . . . ? C12 N1 C6 C7 -21.6(3) . . . . ? C11 N1 C6 C7 110.2(2) . . . . ? C12 N1 C6 C5 155.43(17) . . . . ? C11 N1 C6 C5 -72.7(2) . . . . ? C4 C5 C6 C7 174.11(17) . . . . ? C10 C5 C6 C7 -2.1(3) . . . . ? C4 C5 C6 N1 -3.1(2) . . . . ? C10 C5 C6 N1 -179.30(16) . . . . ? N1 C6 C7 C8 179.04(17) . . . . ? C5 C6 C7 C8 2.0(3) . . . . ? C6 C7 C8 C9 -0.8(3) . . . . ? C7 C8 C9 C10 -0.4(3) . . . . ? C8 C9 C10 C5 0.3(3) . . . . ? C8 C9 C10 C1 -178.15(17) . . . . ? C4 C5 C10 C9 -175.34(16) . . . . ? C6 C5 C10 C9 0.9(2) . . . . ? C4 C5 C10 C1 3.2(2) . . . . ? C6 C5 C10 C1 179.51(15) . . . . ? C2 C1 C10 C9 178.29(17) . . . . ? S1 C1 C10 C9 1.3(2) . . . . ? C2 C1 C10 C5 -0.2(3) . . . . ? S1 C1 C10 C5 -177.16(13) . . . . ? S1 N2 C13 C14 91.22(18) . . . . ? N2 C13 C14 C15 69.6(2) . . . . ? C19 N3 C15 C14 -52.7(2) . . . . ? C20 N3 C15 C14 69.2(2) . . . . ? C16 N3 C15 C14 -169.91(15) . . . . ? C13 C14 C15 N3 -171.87(15) . . . . ? C19 N3 C16 C17 -177.71(17) . . . . ? C20 N3 C16 C17 63.5(2) . . . . ? C15 N3 C16 C17 -58.1(2) . . . . ? N3 C16 C17 C18 -115.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N Br1 0.84(2) 2.58(3) 3.4037(17) 168(2) . _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 66.49 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.252 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.052 _iucr_refine_instructions_details ; TITL cu_d12324_0m in P2(1)/c CELL 1.54178 11.7757 11.5358 16.1129 90.000 94.112 90.000 ZERR 4.00 0.0005 0.0005 0.0007 0.000 0.002 0.000 LATT 1 SYMM -x, y+1/2, -z+1/2 SFAC C H N O S BR UNIT 80 120 12 8 4 4 TEMP -126.180 SIZE 0.010 0.080 0.110 ACTA L.S. 4 FMAP 2 PLAN 20 HTAB N2 Br1 BOND $H CONF WGHT 0.029000 1.110400 FVAR 0.15776 BR1 6 0.522172 0.189227 0.375833 11.00000 0.02368 0.02841 = 0.02271 0.00159 -0.00006 -0.00224 S1 5 0.902719 0.202366 0.408105 11.00000 0.02054 0.02263 = 0.02137 -0.00020 0.00236 0.00261 O1 4 0.861113 0.271303 0.338283 11.00000 0.02809 0.03306 = 0.02116 0.00302 0.00095 0.00264 O2 4 1.000867 0.130438 0.401679 11.00000 0.02360 0.02695 = 0.03077 -0.00203 0.00478 0.00615 N1 3 0.849899 0.612959 0.680792 11.00000 0.03707 0.02594 = 0.02374 -0.00368 0.00150 0.00390 N2 3 0.798694 0.120391 0.429860 11.00000 0.01889 0.02342 = 0.02840 -0.00007 0.00091 0.00221 N3 3 0.638960 0.128414 0.669714 11.00000 0.02650 0.02090 = 0.01857 0.00061 0.00012 -0.00180 C1 1 0.936373 0.297126 0.493679 11.00000 0.02083 0.01995 = 0.02175 0.00401 0.00182 -0.00027 C2 1 1.044877 0.292974 0.530198 11.00000 0.02243 0.02329 = 0.02740 0.00417 0.00112 0.00317 AFIX 43 H2A 2 1.097004 0.236724 0.512668 11.00000 -1.20000 AFIX 0 C3 1 1.079326 0.371876 0.593654 11.00000 0.02327 0.02861 = 0.03155 0.00336 -0.00511 0.00074 AFIX 43 H3A 2 1.155174 0.369780 0.618051 11.00000 -1.20000 AFIX 0 C4 1 1.004199 0.451476 0.620338 11.00000 0.02834 0.02338 = 0.02426 0.00073 -0.00278 -0.00207 AFIX 43 H4A 2 1.029159 0.505717 0.662107 11.00000 -1.20000 AFIX 0 C5 1 0.889811 0.454553 0.586838 11.00000 0.02422 0.01997 = 0.01952 0.00612 0.00192 0.00026 C6 1 0.810679 0.538239 0.615446 11.00000 0.02898 0.02064 = 0.02087 0.00320 0.00584 -0.00068 C7 1 0.703384 0.545382 0.576152 11.00000 0.02758 0.02490 = 0.02888 0.00164 0.00784 0.00586 AFIX 43 H7A 2 0.651484 0.602020 0.593449 11.00000 -1.20000 AFIX 0 C8 1 0.669745 0.469589 0.510568 11.00000 0.02138 0.02783 = 0.03102 0.00251 0.00057 0.00341 AFIX 43 H8A 2 0.594854 0.475484 0.484777 11.00000 -1.20000 AFIX 0 C9 1 0.741775 0.387879 0.483027 11.00000 0.02216 0.02279 = 0.02349 0.00090 0.00068 0.00117 AFIX 43 H9A 2 0.716663 0.337420 0.438862 11.00000 -1.20000 AFIX 0 C10 1 0.854309 0.378188 0.520342 11.00000 0.01980 0.01961 = 0.02068 0.00532 0.00227 -0.00070 C11 1 0.865546 0.558670 0.762504 11.00000 0.09381 0.05063 = 0.02275 -0.00120 -0.00217 0.01853 AFIX 137 H11A 2 0.900376 0.482136 0.757096 11.00000 -1.50000 H11B 2 0.791492 0.550123 0.785968 11.00000 -1.50000 H11C 2 0.915291 0.607251 0.799384 11.00000 -1.50000 AFIX 0 C12 1 0.790033 0.722898 0.685433 11.00000 0.04077 0.03039 = 0.03775 -0.00944 0.00623 0.00355 AFIX 137 H12A 2 0.781528 0.758186 0.630010 11.00000 -1.50000 H12B 2 0.833627 0.775038 0.723716 11.00000 -1.50000 H12C 2 0.714635 0.709492 0.705697 11.00000 -1.50000 AFIX 0 C13 1 0.813007 0.024362 0.488648 11.00000 0.02556 0.02023 = 0.03554 0.00053 0.00614 0.00354 AFIX 23 H13A 2 0.891248 -0.006491 0.486887 11.00000 -1.20000 H13B 2 0.759571 -0.038326 0.470242 11.00000 -1.20000 AFIX 0 C14 1 0.793063 0.055570 0.578551 11.00000 0.02292 0.02539 = 0.02996 0.00448 0.00074 0.00216 AFIX 23 H14A 2 0.817741 -0.009390 0.615741 11.00000 -1.20000 H14B 2 0.838608 0.124790 0.595666 11.00000 -1.20000 AFIX 0 C15 1 0.667578 0.080193 0.586244 11.00000 0.02302 0.02451 = 0.01997 -0.00226 0.00108 -0.00036 AFIX 23 H15A 2 0.641419 0.136057 0.542307 11.00000 -1.20000 H15B 2 0.624420 0.007366 0.575808 11.00000 -1.20000 AFIX 0 C16 1 0.510293 0.127952 0.673462 11.00000 0.02753 0.02906 = 0.02556 -0.00132 0.00790 -0.00150 AFIX 23 H16A 2 0.483101 0.046749 0.670517 11.00000 -1.20000 H16B 2 0.491431 0.159961 0.727799 11.00000 -1.20000 AFIX 0 C17 1 0.448093 0.195741 0.605846 11.00000 0.02650 0.05593 = 0.02764 0.00309 0.00741 0.00627 AFIX 43 H17A 2 0.451528 0.170839 0.549883 11.00000 -1.20000 AFIX 0 C18 1 0.389410 0.287617 0.620826 11.00000 0.05865 0.06642 = 0.05297 0.02719 0.02359 0.02765 AFIX 93 H18A 2 0.385063 0.313736 0.676423 11.00000 -1.20000 H18B 2 0.350786 0.328777 0.576198 11.00000 -1.20000 AFIX 0 C19 1 0.686982 0.052843 0.739414 11.00000 0.03991 0.03061 = 0.02378 0.00776 -0.00340 -0.00124 AFIX 137 H19A 2 0.659224 0.079601 0.792022 11.00000 -1.50000 H19B 2 0.770303 0.057033 0.742641 11.00000 -1.50000 H19C 2 0.662795 -0.027477 0.729115 11.00000 -1.50000 AFIX 0 C20 1 0.683688 0.249596 0.681688 11.00000 0.03694 0.02162 = 0.02438 -0.00187 0.00226 -0.00680 AFIX 137 H20A 2 0.657836 0.281675 0.733404 11.00000 -1.50000 H20B 2 0.655326 0.297924 0.634653 11.00000 -1.50000 H20C 2 0.767098 0.248287 0.684820 11.00000 -1.50000 AFIX 0 H2N 2 0.734840 0.146943 0.413512 11.00000 0.02826 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM cu_d12324_0m in P2(1)/c REM R1 = 0.0248 for 3420 Fo > 4sig(Fo) and 0.0282 for all 3752 data REM 252 parameters refined using 0 restraints END WGHT 0.0289 1.1073 REM Highest difference peak 0.252, deepest hole -0.304, 1-sigma level 0.052 Q1 1 0.8548 0.4945 0.5991 11.00000 0.05 0.25 Q2 1 0.9215 0.2542 0.4598 11.00000 0.05 0.24 Q3 1 0.8954 0.3414 0.5015 11.00000 0.05 0.23 Q4 1 0.6553 0.1054 0.6294 11.00000 0.05 0.23 Q5 1 0.7421 0.5235 0.6117 11.00000 0.05 0.22 Q6 1 0.8782 0.4177 0.5527 11.00000 0.05 0.22 Q7 1 0.9973 0.3121 0.4970 11.00000 0.05 0.22 Q8 1 0.8228 0.5695 0.6524 11.00000 0.05 0.22 Q9 1 0.8516 0.1462 0.4223 11.00000 0.05 0.21 Q10 1 0.4811 0.0803 0.3735 11.00000 0.05 0.21 Q11 1 0.9445 0.4604 0.5910 11.00000 0.05 0.21 Q12 1 0.7304 0.0655 0.5914 11.00000 0.05 0.21 Q13 1 0.4621 0.2592 0.6192 11.00000 0.05 0.21 Q14 1 0.4805 0.1649 0.6308 11.00000 0.05 0.20 Q15 1 0.4999 0.2788 0.3302 11.00000 0.05 0.20 Q16 1 0.5365 0.1276 0.3407 11.00000 0.05 0.20 Q17 1 0.5151 0.2557 0.3180 11.00000 0.05 0.20 Q18 1 0.8682 0.5831 0.7154 11.00000 0.05 0.19 Q19 1 0.8014 0.3810 0.5076 11.00000 0.05 0.19 Q20 1 0.6197 0.7596 0.7353 11.00000 0.05 0.19 ; _database_code_depnum_ccdc_archive 'CCDC 971464' ####################################################################### # # 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_k1177 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H25 N3 O2 S' _chemical_formula_sum 'C17 H25 N3 O2 S' _chemical_formula_weight 335.46 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5518(3) _cell_length_b 12.7906(3) _cell_length_c 13.4228(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.5820(13) _cell_angle_gamma 90.00 _cell_volume 1774.71(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 15607 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.195 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.658 _exptl_absorpt_correction_T_max 1.005 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 15607 _diffrn_reflns_av_R_equivalents 0.0778 _diffrn_reflns_av_sigmaI/netI 0.0620 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4028 _reflns_number_gt 2656 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0794P)^2^+0.2813P] 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 4028 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0938 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1567 _refine_ls_wR_factor_gt 0.1321 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.59798(5) 0.78655(4) 0.43586(4) 0.03326(19) Uani 1 1 d . . . O1 O 0.67185(14) 0.75965(12) 0.36132(12) 0.0391(4) Uani 1 1 d . . . O2 O 0.63556(14) 0.87775(12) 0.49733(12) 0.0436(4) Uani 1 1 d . . . N1 N 0.02807(18) 0.71762(16) 0.14255(15) 0.0448(5) Uani 1 1 d . . . N2 N 0.59578(19) 0.68684(15) 0.50628(14) 0.0350(5) Uani 1 1 d . . . H1N H 0.632(2) 0.634(2) 0.492(2) 0.058(8) Uiso 1 1 d . . . N3 N 0.26225(18) 0.49763(14) 0.51242(15) 0.0396(5) Uani 1 1 d . . . C1 C 0.4331(2) 0.80756(16) 0.37578(16) 0.0308(5) Uani 1 1 d . . . C2 C 0.3730(2) 0.89191(16) 0.40822(17) 0.0364(5) Uani 1 1 d . . . H2A H 0.4197 0.9367 0.4591 0.044 Uiso 1 1 calc R . . C3 C 0.2419(2) 0.91275(17) 0.36642(18) 0.0402(6) Uani 1 1 d . . . H3A H 0.2008 0.9720 0.3886 0.048 Uiso 1 1 calc R . . C4 C 0.1740(2) 0.84817(17) 0.29441(18) 0.0394(6) Uani 1 1 d . . . H4A H 0.0859 0.8634 0.2668 0.047 Uiso 1 1 calc R . . C5 C 0.2315(2) 0.75872(16) 0.25950(16) 0.0323(5) Uani 1 1 d . . . C6 C 0.1609(2) 0.69190(17) 0.18282(17) 0.0358(5) Uani 1 1 d . . . C7 C 0.2219(2) 0.60883(18) 0.14880(17) 0.0405(6) Uani 1 1 d . . . H7A H 0.1751 0.5652 0.0969 0.049 Uiso 1 1 calc R . . C8 C 0.3525(2) 0.58689(17) 0.18929(17) 0.0371(5) Uani 1 1 d . . . H8A H 0.3925 0.5283 0.1649 0.044 Uiso 1 1 calc R . . C9 C 0.4231(2) 0.64898(15) 0.26360(16) 0.0322(5) Uani 1 1 d . . . H9A H 0.5111 0.6326 0.2907 0.039 Uiso 1 1 calc R . . C10 C 0.3656(2) 0.73716(15) 0.30013(16) 0.0295(5) Uani 1 1 d . . . C11 C -0.0211(3) 0.6810(2) 0.0387(2) 0.0606(8) Uani 1 1 d . . . H11A H 0.0379 0.7030 -0.0052 0.091 Uiso 1 1 calc R . . H11B H -0.1070 0.7109 0.0132 0.091 Uiso 1 1 calc R . . H11C H -0.0272 0.6045 0.0384 0.091 Uiso 1 1 calc R . . C12 C -0.0596(3) 0.6885(2) 0.2097(2) 0.0603(7) Uani 1 1 d . . . H12A H -0.0287 0.7190 0.2772 0.090 Uiso 1 1 calc R . . H12B H -0.0622 0.6122 0.2155 0.090 Uiso 1 1 calc R . . H12C H -0.1467 0.7148 0.1814 0.090 Uiso 1 1 calc R . . C13 C 0.5415(2) 0.69038(18) 0.59837(17) 0.0403(6) Uani 1 1 d . . . H13A H 0.4906 0.7554 0.5984 0.048 Uiso 1 1 calc R . . H13B H 0.6128 0.6917 0.6588 0.048 Uiso 1 1 calc R . . C14 C 0.4552(2) 0.59663(17) 0.60505(17) 0.0389(6) Uani 1 1 d . . . H14A H 0.5048 0.5317 0.6005 0.047 Uiso 1 1 calc R . . H14B H 0.4292 0.5971 0.6719 0.047 Uiso 1 1 calc R . . C15 C 0.3352(2) 0.59659(16) 0.52154(18) 0.0393(5) Uani 1 1 d . . . H15A H 0.2776 0.6539 0.5346 0.047 Uiso 1 1 calc R . . H15B H 0.3608 0.6114 0.4559 0.047 Uiso 1 1 calc R . . C16 C 0.1965(3) 0.4823(2) 0.5981(2) 0.0561(7) Uani 1 1 d . . . H16A H 0.2609 0.4804 0.6619 0.084 Uiso 1 1 calc R . . H16B H 0.1486 0.4162 0.5893 0.084 Uiso 1 1 calc R . . H16C H 0.1363 0.5402 0.6003 0.084 Uiso 1 1 calc R . . C17 C 0.1682(2) 0.4954(2) 0.4161(2) 0.0537(7) Uani 1 1 d . . . H17A H 0.2134 0.5038 0.3596 0.081 Uiso 1 1 calc R . . H17B H 0.1060 0.5526 0.4149 0.081 Uiso 1 1 calc R . . H17C H 0.1223 0.4284 0.4094 0.081 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 0.0311(3) 0.0315(3) 0.0341(3) 0.0013(2) -0.0006(2) -0.0024(2) O1 0.0317(8) 0.0497(10) 0.0356(9) 0.0045(7) 0.0061(7) -0.0059(7) O2 0.0400(9) 0.0323(8) 0.0515(11) -0.0072(7) -0.0077(8) -0.0053(7) N1 0.0309(11) 0.0593(13) 0.0397(12) 0.0013(9) -0.0040(9) -0.0083(9) N2 0.0439(11) 0.0316(10) 0.0300(11) 0.0017(8) 0.0087(9) 0.0092(8) N3 0.0395(11) 0.0403(11) 0.0429(12) 0.0056(9) 0.0179(9) 0.0071(8) C1 0.0310(11) 0.0287(11) 0.0312(12) 0.0060(8) 0.0024(9) -0.0039(8) C2 0.0370(12) 0.0317(12) 0.0369(13) 0.0001(9) -0.0007(10) -0.0011(9) C3 0.0396(13) 0.0329(12) 0.0459(15) 0.0001(10) 0.0031(11) 0.0067(9) C4 0.0299(12) 0.0406(13) 0.0453(14) 0.0060(10) 0.0018(10) 0.0046(9) C5 0.0330(12) 0.0337(11) 0.0290(12) 0.0067(9) 0.0029(9) -0.0030(9) C6 0.0326(12) 0.0405(12) 0.0324(12) 0.0067(10) 0.0016(10) -0.0066(9) C7 0.0458(14) 0.0402(13) 0.0327(13) -0.0047(10) 0.0012(11) -0.0128(10) C8 0.0425(13) 0.0358(12) 0.0335(12) -0.0008(9) 0.0090(10) -0.0033(9) C9 0.0328(11) 0.0329(11) 0.0303(12) 0.0045(9) 0.0052(9) -0.0018(9) C10 0.0333(11) 0.0278(11) 0.0271(11) 0.0057(9) 0.0051(9) -0.0040(8) C11 0.0470(16) 0.081(2) 0.0451(16) -0.0033(14) -0.0106(13) -0.0070(14) C12 0.0393(15) 0.0765(19) 0.0632(19) 0.0011(15) 0.0059(13) -0.0132(13) C13 0.0473(14) 0.0430(13) 0.0306(13) -0.0012(10) 0.0081(11) 0.0095(10) C14 0.0512(14) 0.0394(13) 0.0297(12) 0.0041(10) 0.0168(11) 0.0110(10) C15 0.0424(13) 0.0349(12) 0.0438(14) 0.0081(10) 0.0164(11) 0.0098(9) C16 0.0559(16) 0.0584(16) 0.0652(19) 0.0048(14) 0.0389(15) 0.0077(12) C17 0.0429(14) 0.0560(16) 0.0615(18) 0.0098(13) 0.0086(13) 0.0047(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4283(16) . ? S1 O2 1.4379(15) . ? S1 N2 1.5904(19) . ? S1 C1 1.785(2) . ? N1 C6 1.435(3) . ? N1 C11 1.464(3) . ? N1 C12 1.464(3) . ? N2 C13 1.464(3) . ? N3 C17 1.463(3) . ? N3 C16 1.471(3) . ? N3 C15 1.474(3) . ? C1 C2 1.367(3) . ? C1 C10 1.435(3) . ? C2 C3 1.410(3) . ? C3 C4 1.361(3) . ? C4 C5 1.418(3) . ? C5 C6 1.427(3) . ? C5 C10 1.437(3) . ? C6 C7 1.367(3) . ? C7 C8 1.405(3) . ? C8 C9 1.372(3) . ? C9 C10 1.414(3) . ? C13 C14 1.519(3) . ? C14 C15 1.513(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 O1 S1 O2 118.10(9) . . ? O1 S1 N2 107.36(10) . . ? O2 S1 N2 110.16(10) . . ? O1 S1 C1 109.83(10) . . ? O2 S1 C1 105.58(9) . . ? N2 S1 C1 105.07(10) . . ? C6 N1 C11 114.7(2) . . ? C6 N1 C12 113.57(19) . . ? C11 N1 C12 111.0(2) . . ? C13 N2 S1 122.15(15) . . ? C17 N3 C16 110.23(19) . . ? C17 N3 C15 109.88(18) . . ? C16 N3 C15 111.69(19) . . ? C2 C1 C10 121.7(2) . . ? C2 C1 S1 116.60(17) . . ? C10 C1 S1 121.70(16) . . ? C1 C2 C3 120.2(2) . . ? C4 C3 C2 120.2(2) . . ? C3 C4 C5 121.7(2) . . ? C4 C5 C6 121.7(2) . . ? C4 C5 C10 118.9(2) . . ? C6 C5 C10 119.4(2) . . ? C7 C6 C5 119.6(2) . . ? C7 C6 N1 122.8(2) . . ? C5 C6 N1 117.6(2) . . ? C6 C7 C8 121.1(2) . . ? C9 C8 C7 120.9(2) . . ? C8 C9 C10 120.4(2) . . ? C9 C10 C1 124.0(2) . . ? C9 C10 C5 118.7(2) . . ? C1 C10 C5 117.32(19) . . ? N2 C13 C14 111.49(18) . . ? C15 C14 C13 112.27(18) . . ? N3 C15 C14 114.03(18) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H1N N3 0.82(3) 2.03(3) 2.833(3) 168(3) 3_666 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.380 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.060 _iucr_refine_instructions_details ; TITL k1177 in P2(1)/c CELL 0.71073 10.5518 12.7906 13.4228 90.000 101.582 90.000 ZERR 4 0.0003 0.0003 0.0004 0.0000 0.0013 0.0000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O S DISP C 0.00330 0.00160 DISP H 0.00000 0.00000 DISP N 0.00610 0.00330 DISP O 0.01060 0.00600 DISP S 0.12460 0.12340 UNIT 68 100 12 8 4 TEMP -123 SIZE 0.35, 0.30, 0.05 ACTA BOND FMAP 2 PLAN 20 L.S. 4 EQIV $1 -x+1, -y+1, -z+1 HTAB N2 N3_$1 WGHT 0.079400 0.281300 FVAR 0.46022 S1 5 0.597985 0.786547 0.435856 11.00000 0.03114 0.03154 = 0.03410 0.00126 -0.00061 -0.00235 O1 4 0.671849 0.759645 0.361315 11.00000 0.03169 0.04968 = 0.03561 0.00451 0.00609 -0.00592 O2 4 0.635564 0.877746 0.497330 11.00000 0.04004 0.03231 = 0.05152 -0.00717 -0.00769 -0.00526 N1 3 0.028073 0.717621 0.142546 11.00000 0.03088 0.05927 = 0.03968 0.00128 -0.00397 -0.00830 N2 3 0.595783 0.686845 0.506282 11.00000 0.04391 0.03163 = 0.02995 0.00166 0.00873 0.00919 H1N 2 0.631802 0.633741 0.492001 11.00000 0.05791 N3 3 0.262247 0.497628 0.512421 11.00000 0.03946 0.04033 = 0.04291 0.00558 0.01793 0.00712 C1 1 0.433112 0.807555 0.375781 11.00000 0.03097 0.02870 = 0.03122 0.00601 0.00236 -0.00388 C2 1 0.372962 0.891913 0.408222 11.00000 0.03704 0.03175 = 0.03690 0.00006 -0.00069 -0.00114 AFIX 43 H2A 2 0.419658 0.936680 0.459138 11.00000 -1.20000 AFIX 0 C3 1 0.241889 0.912750 0.366418 11.00000 0.03957 0.03289 = 0.04589 0.00009 0.00306 0.00674 AFIX 43 H3A 2 0.200838 0.972018 0.388576 11.00000 -1.20000 AFIX 0 C4 1 0.174031 0.848172 0.294405 11.00000 0.02989 0.04065 = 0.04527 0.00597 0.00181 0.00459 AFIX 43 H4A 2 0.085856 0.863405 0.266799 11.00000 -1.20000 AFIX 0 C5 1 0.231530 0.758721 0.259498 11.00000 0.03299 0.03366 = 0.02899 0.00667 0.00289 -0.00302 C6 1 0.160867 0.691900 0.182816 11.00000 0.03260 0.04045 = 0.03239 0.00672 0.00160 -0.00664 C7 1 0.221853 0.608829 0.148798 11.00000 0.04579 0.04016 = 0.03272 -0.00470 0.00120 -0.01279 AFIX 43 H7A 2 0.175076 0.565197 0.096886 11.00000 -1.20000 AFIX 0 C8 1 0.352489 0.586890 0.189288 11.00000 0.04248 0.03575 = 0.03351 -0.00080 0.00904 -0.00330 AFIX 43 H8A 2 0.392464 0.528286 0.164891 11.00000 -1.20000 AFIX 0 C9 1 0.423117 0.648978 0.263604 11.00000 0.03281 0.03287 = 0.03034 0.00450 0.00521 -0.00175 AFIX 43 H9A 2 0.511119 0.632634 0.290673 11.00000 -1.20000 AFIX 0 C10 1 0.365641 0.737163 0.300127 11.00000 0.03334 0.02780 = 0.02705 0.00567 0.00505 -0.00398 C11 1 -0.021133 0.680978 0.038685 11.00000 0.04705 0.08149 = 0.04506 -0.00333 -0.01063 -0.00700 AFIX 137 H11A 2 0.037894 0.702965 -0.005152 11.00000 -1.50000 H11B 2 -0.107025 0.710914 0.013233 11.00000 -1.50000 H11C 2 -0.027215 0.604521 0.038430 11.00000 -1.50000 AFIX 0 C12 1 -0.059625 0.688497 0.209715 11.00000 0.03927 0.07652 = 0.06324 0.00114 0.00588 -0.01319 AFIX 137 H12A 2 -0.028704 0.719032 0.277179 11.00000 -1.50000 H12B 2 -0.062226 0.612182 0.215485 11.00000 -1.50000 H12C 2 -0.146656 0.714779 0.181446 11.00000 -1.50000 AFIX 0 C13 1 0.541504 0.690377 0.598369 11.00000 0.04729 0.04297 = 0.03061 -0.00117 0.00808 0.00952 AFIX 23 H13A 2 0.490578 0.755377 0.598418 11.00000 -1.20000 H13B 2 0.612822 0.691691 0.658837 11.00000 -1.20000 AFIX 0 C14 1 0.455215 0.596633 0.605047 11.00000 0.05120 0.03939 = 0.02972 0.00413 0.01680 0.01100 AFIX 23 H14A 2 0.504802 0.531701 0.600496 11.00000 -1.20000 H14B 2 0.429160 0.597052 0.671907 11.00000 -1.20000 AFIX 0 C15 1 0.335203 0.596594 0.521542 11.00000 0.04240 0.03491 = 0.04385 0.00813 0.01637 0.00981 AFIX 23 H15A 2 0.277571 0.653891 0.534560 11.00000 -1.20000 H15B 2 0.360841 0.611353 0.455931 11.00000 -1.20000 AFIX 0 C16 1 0.196529 0.482344 0.598135 11.00000 0.05588 0.05844 = 0.06520 0.00475 0.03885 0.00767 AFIX 137 H16A 2 0.260891 0.480376 0.661868 11.00000 -1.50000 H16B 2 0.148612 0.416245 0.589342 11.00000 -1.50000 H16C 2 0.136295 0.540228 0.600309 11.00000 -1.50000 AFIX 0 C17 1 0.168222 0.495436 0.416143 11.00000 0.04293 0.05598 = 0.06154 0.00981 0.00864 0.00474 AFIX 137 H17A 2 0.213376 0.503844 0.359575 11.00000 -1.50000 H17B 2 0.106048 0.552568 0.414935 11.00000 -1.50000 H17C 2 0.122258 0.428426 0.409428 11.00000 -1.50000 HKLF 4 REM k1177 in P2(1)/c REM R1 = 0.0551 for 2656 Fo > 4sig(Fo) and 0.0938 for all 4028 data REM 216 parameters refined using 0 restraints END WGHT 0.0780 0.3089 REM Highest difference peak 0.380, deepest hole -0.394, 1-sigma level 0.060 Q1 1 0.0016 0.7058 0.1177 11.00000 0.05 0.32 Q2 1 0.6361 0.7650 0.2966 11.00000 0.05 0.28 Q3 1 0.6860 0.7186 0.2853 11.00000 0.05 0.26 Q4 1 0.5970 0.7625 0.5089 11.00000 0.05 0.23 Q5 1 0.4517 0.6425 0.2752 11.00000 0.05 0.22 Q6 1 0.5196 0.7079 0.5971 11.00000 0.05 0.22 Q7 1 0.4035 0.8244 0.3152 11.00000 0.05 0.22 Q8 1 0.6149 0.7509 0.3709 11.00000 0.05 0.21 Q9 1 0.1948 0.7197 0.2038 11.00000 0.05 0.21 Q10 1 0.6058 0.8868 0.4283 11.00000 0.05 0.20 Q11 1 0.3372 0.6020 0.4371 11.00000 0.05 0.20 Q12 1 0.1754 0.6311 0.2061 11.00000 0.05 0.20 Q13 1 0.5973 0.6334 0.4306 11.00000 0.05 0.20 Q14 1 -0.0371 0.7750 0.2893 11.00000 0.05 0.19 Q15 1 0.3886 0.5983 0.2422 11.00000 0.05 0.19 Q16 1 0.2145 0.8191 0.2677 11.00000 0.05 0.19 Q17 1 0.3943 0.7683 0.3529 11.00000 0.05 0.18 Q18 1 0.2321 0.5219 0.6511 11.00000 0.05 0.18 Q19 1 0.3964 0.8265 0.4086 11.00000 0.05 0.18 Q20 1 0.2132 0.6577 0.1444 11.00000 0.05 0.18 ; _database_code_depnum_ccdc_archive 'CCDC 971465'