Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Wisner, James' _publ_contact_author_email jwisner@uwo.ca _publ_section_title ; Minimal Complementary Hydrogen-Bonded Double Helices ; loop_ _publ_author_name H.-B.Wang B.Mudraboyina J.Li J.Wisner # Attachment 'CCDC783459.cif' data_b10039_0m _database_code_depnum_ccdc_archive 'CCDC 783459' #TrackingRef 'CCDC783459.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H39 Cl3 N6 O6 S3' _chemical_formula_weight 950.34 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 12.1851(4) _cell_length_b 12.7756(4) _cell_length_c 15.7666(5) _cell_angle_alpha 82.4650(10) _cell_angle_beta 77.9780(10) _cell_angle_gamma 70.3200(10) _cell_volume 2255.40(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9852 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 23.51 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.397 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9728 _exptl_absorpt_correction_T_max 0.9863 _exptl_absorpt_process_details SAINT _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 143783 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 31.06 _reflns_number_total 14429 _reflns_number_gt 9895 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+1.4345P] 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 14429 _refine_ls_number_parameters 563 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1181 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.27275(4) 0.20753(4) 0.35908(3) 0.02156(9) Uani 1 1 d . . . S2 S 1.13713(4) -0.03041(4) 0.13699(3) 0.02513(10) Uani 1 1 d . . . S3 S 0.69329(4) -0.19149(4) 0.17449(3) 0.02313(10) Uani 1 1 d . . . C1 C 0.93662(18) 0.36621(16) 0.12267(13) 0.0282(4) Uani 1 1 d . . . H1 H 0.9797 0.3440 0.1693 0.034 Uiso 1 1 calc R . . C2 C 0.8868(2) 0.47871(17) 0.09997(15) 0.0355(5) Uani 1 1 d . . . H2 H 0.8964 0.5331 0.1309 0.043 Uiso 1 1 calc R . . C3 C 0.8235(2) 0.51169(17) 0.03261(15) 0.0377(5) Uani 1 1 d . . . H3 H 0.7888 0.5887 0.0176 0.045 Uiso 1 1 calc R . . C4 C 0.8107(2) 0.43223(17) -0.01317(15) 0.0388(5) Uani 1 1 d . . . H4 H 0.7677 0.4549 -0.0598 0.047 Uiso 1 1 calc R . . C5 C 0.86065(19) 0.31959(16) 0.00890(13) 0.0301(4) Uani 1 1 d . . . H5 H 0.8518 0.2655 -0.0228 0.036 Uiso 1 1 calc R . . C6 C 0.92353(16) 0.28563(14) 0.07724(12) 0.0217(3) Uani 1 1 d . . . C7 C 0.97039(15) 0.16484(14) 0.10346(11) 0.0195(3) Uani 1 1 d . . . C8 C 1.08377(15) 0.11276(15) 0.11510(12) 0.0229(3) Uani 1 1 d . . . C9 C 1.17912(18) 0.16724(19) 0.10338(16) 0.0370(5) Uani 1 1 d . . . H9A H 1.1607 0.2331 0.0627 0.055 Uiso 1 1 calc R . . H9B H 1.2558 0.1143 0.0802 0.055 Uiso 1 1 calc R . . H9C H 1.1826 0.1897 0.1596 0.055 Uiso 1 1 calc R . . C10 C 1.00905(15) -0.06461(15) 0.16864(12) 0.0234(3) Uani 1 1 d . . . H10 H 1.0121 -0.1339 0.2002 0.028 Uiso 1 1 calc R . . C11 C 0.90411(15) 0.00433(13) 0.14995(11) 0.0189(3) Uani 1 1 d . . . C12 C 0.79887(14) -0.03500(13) 0.17181(11) 0.0185(3) Uani 1 1 d . . . C13 C 0.80622(16) -0.13437(14) 0.14620(12) 0.0235(4) Uani 1 1 d . . . H13 H 0.8774 -0.1748 0.1108 0.028 Uiso 1 1 calc R . . C14 C 0.58224(16) -0.08603(15) 0.22800(12) 0.0234(4) Uani 1 1 d . . . H14 H 0.5060 -0.0943 0.2456 0.028 Uiso 1 1 calc R . . C15 C 0.59745(14) 0.00794(13) 0.24642(11) 0.0182(3) Uani 1 1 d . . . C16 C 0.50159(14) 0.08817(13) 0.30379(11) 0.0181(3) Uani 1 1 d . . . C17 C 0.38798(15) 0.12143(14) 0.29171(12) 0.0212(3) Uani 1 1 d . . . H17 H 0.3709 0.0959 0.2435 0.025 Uiso 1 1 calc R . . C18 C 0.25852(18) 0.30409(18) 0.50664(14) 0.0334(4) Uani 1 1 d . . . H18A H 0.2904 0.2831 0.5608 0.050 Uiso 1 1 calc R . . H18B H 0.1814 0.2923 0.5153 0.050 Uiso 1 1 calc R . . H18C H 0.2491 0.3828 0.4897 0.050 Uiso 1 1 calc R . . C19 C 0.34261(15) 0.23343(14) 0.43595(12) 0.0221(3) Uani 1 1 d . . . C20 C 0.46183(15) 0.18971(13) 0.43182(11) 0.0191(3) Uani 1 1 d . . . C21 C 0.52292(15) 0.21177(15) 0.49698(12) 0.0220(3) Uani 1 1 d . . . C22 C 0.5227(2) 0.31850(18) 0.50506(17) 0.0426(6) Uani 1 1 d . . . H22 H 0.4806 0.3794 0.4705 0.051 Uiso 1 1 calc R . . C23 C 0.5844(3) 0.3366(2) 0.5639(2) 0.0566(8) Uani 1 1 d . . . H23 H 0.5839 0.4100 0.5692 0.068 Uiso 1 1 calc R . . C24 C 0.6459(2) 0.2494(2) 0.61440(16) 0.0420(5) Uani 1 1 d . . . H24 H 0.6880 0.2625 0.6542 0.050 Uiso 1 1 calc R . . C25 C 0.64632(17) 0.14259(18) 0.60698(13) 0.0306(4) Uani 1 1 d . . . H25 H 0.6882 0.0821 0.6420 0.037 Uiso 1 1 calc R . . C26 C 0.58555(16) 0.12374(16) 0.54835(12) 0.0254(4) Uani 1 1 d . . . H26 H 0.5866 0.0501 0.5432 0.030 Uiso 1 1 calc R . . N1 N 0.78331(13) 0.06629(13) 0.37554(10) 0.0216(3) Uani 1 1 d . . . C27 C 0.84112(17) -0.03638(16) 0.40458(13) 0.0286(4) Uani 1 1 d . . . H27 H 0.7985 -0.0880 0.4214 0.034 Uiso 1 1 calc R . . C28 C 0.95955(19) -0.07178(18) 0.41157(14) 0.0344(5) Uani 1 1 d . . . H28 H 0.9975 -0.1458 0.4323 0.041 Uiso 1 1 calc R . . C29 C 1.02092(18) 0.00374(19) 0.38749(14) 0.0348(5) Uani 1 1 d . . . H29 H 1.1024 -0.0176 0.3914 0.042 Uiso 1 1 calc R . . C30 C 0.96251(16) 0.11116(17) 0.35746(13) 0.0280(4) Uani 1 1 d . . . H30 H 1.0034 0.1642 0.3408 0.034 Uiso 1 1 calc R . . C31 C 0.84367(15) 0.14011(15) 0.35209(11) 0.0207(3) Uani 1 1 d . . . C32 C 0.77438(15) 0.25100(14) 0.31631(11) 0.0203(3) Uani 1 1 d . . . C33 C 0.77700(18) 0.35395(16) 0.33635(12) 0.0272(4) Uani 1 1 d . . . C34 C 0.8533(2) 0.3643(2) 0.39737(16) 0.0444(6) Uani 1 1 d . . . H34A H 0.8217 0.4390 0.4191 0.067 Uiso 1 1 calc R . . H34B H 0.9346 0.3520 0.3661 0.067 Uiso 1 1 calc R . . H34C H 0.8531 0.3085 0.4463 0.067 Uiso 1 1 calc R . . C35 C 0.70421(18) 0.44915(16) 0.29838(13) 0.0287(4) Uani 1 1 d . . . H35 H 0.7041 0.5199 0.3110 0.034 Uiso 1 1 calc R . . C36 C 0.63139(16) 0.44478(14) 0.24239(13) 0.0244(4) Uani 1 1 d . . . C37 C 0.55725(19) 0.54996(16) 0.19956(16) 0.0345(5) Uani 1 1 d . . . H37A H 0.5536 0.5359 0.1407 0.052 Uiso 1 1 calc R . . H37B H 0.5929 0.6089 0.1964 0.052 Uiso 1 1 calc R . . H37C H 0.4770 0.5734 0.2337 0.052 Uiso 1 1 calc R . . C38 C 0.63568(14) 0.33807(14) 0.22598(11) 0.0192(3) Uani 1 1 d . . . C39 C 0.56520(15) 0.31722(13) 0.16688(11) 0.0189(3) Uani 1 1 d . . . C40 C 0.44284(16) 0.36440(14) 0.17842(12) 0.0233(3) Uani 1 1 d . . . H40 H 0.4018 0.4152 0.2222 0.028 Uiso 1 1 calc R . . C41 C 0.38175(16) 0.33583(15) 0.12482(13) 0.0262(4) Uani 1 1 d . . . H41 H 0.2979 0.3655 0.1323 0.031 Uiso 1 1 calc R . . C42 C 0.44417(17) 0.26411(18) 0.06083(13) 0.0303(4) Uani 1 1 d . . . H42 H 0.4045 0.2450 0.0223 0.036 Uiso 1 1 calc R . . C43 C 0.56651(17) 0.22014(17) 0.05364(13) 0.0304(4) Uani 1 1 d . . . H43 H 0.6092 0.1703 0.0095 0.036 Uiso 1 1 calc R . . N2 N 0.70458(12) 0.24481(11) 0.26238(9) 0.0180(3) Uani 1 1 d . . . N3 N 0.62753(13) 0.24448(13) 0.10602(10) 0.0240(3) Uani 1 1 d . . . N4 N 0.88604(12) 0.11101(11) 0.11538(9) 0.0189(3) Uani 1 1 d . . . H4A H 0.8172 0.1477 0.0998 0.023 Uiso 1 1 calc R . . N5 N 0.70040(12) 0.03360(11) 0.21975(9) 0.0184(3) Uani 1 1 d . . . H5A H 0.7032 0.0968 0.2341 0.022 Uiso 1 1 calc R . . N6 N 0.53774(12) 0.11982(12) 0.37006(9) 0.0190(3) Uani 1 1 d . . . H6 H 0.6135 0.0942 0.3734 0.023 Uiso 1 1 calc R . . O1 O 0.21778(12) 0.31063(11) 0.31151(9) 0.0320(3) Uani 1 1 d . . . O2 O 0.19168(12) 0.14805(12) 0.40085(10) 0.0333(3) Uani 1 1 d . . . O3 O 0.72543(13) -0.28678(11) 0.23543(11) 0.0359(3) Uani 1 1 d . . . O4 O 0.66027(14) -0.21347(13) 0.09780(10) 0.0381(4) Uani 1 1 d . . . O5 O 1.20369(13) -0.05555(13) 0.20718(10) 0.0378(3) Uani 1 1 d . . . O6 O 1.20097(13) -0.08230(13) 0.05707(11) 0.0410(4) Uani 1 1 d . . . C44 C 0.1078(2) 0.57247(18) 0.30088(16) 0.0406(5) Uani 1 1 d . . . H44 H 0.1412 0.4910 0.2918 0.049 Uiso 1 1 calc R . . Cl1 Cl -0.03498(6) 0.62352(5) 0.27506(4) 0.04783(15) Uani 1 1 d . . . Cl2 Cl 0.20119(6) 0.64156(5) 0.23318(5) 0.05299(17) Uani 1 1 d . . . Cl3 Cl 0.10131(9) 0.59213(6) 0.41046(5) 0.0714(2) 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 0.01538(18) 0.0212(2) 0.0266(2) -0.00151(16) -0.00419(16) -0.00374(15) S2 0.01584(19) 0.0259(2) 0.0319(2) -0.00541(18) -0.00237(17) -0.00424(16) S3 0.0245(2) 0.01733(19) 0.0306(2) -0.00789(17) -0.00288(17) -0.00948(16) C1 0.0335(10) 0.0276(9) 0.0288(10) -0.0049(8) -0.0039(8) -0.0163(8) C2 0.0457(12) 0.0254(10) 0.0393(12) -0.0086(9) -0.0018(10) -0.0174(9) C3 0.0481(13) 0.0206(9) 0.0432(13) 0.0023(9) -0.0076(10) -0.0115(9) C4 0.0520(14) 0.0269(10) 0.0388(12) 0.0053(9) -0.0193(10) -0.0105(9) C5 0.0408(11) 0.0244(9) 0.0286(10) -0.0010(8) -0.0103(8) -0.0126(8) C6 0.0234(8) 0.0204(8) 0.0223(9) -0.0022(7) -0.0006(7) -0.0102(7) C7 0.0205(8) 0.0210(8) 0.0184(8) -0.0034(6) -0.0011(6) -0.0090(6) C8 0.0206(8) 0.0256(9) 0.0245(9) -0.0019(7) -0.0026(7) -0.0106(7) C9 0.0240(9) 0.0394(11) 0.0516(14) 0.0000(10) -0.0060(9) -0.0170(9) C10 0.0197(8) 0.0199(8) 0.0294(9) -0.0017(7) -0.0021(7) -0.0061(6) C11 0.0197(8) 0.0162(7) 0.0207(8) -0.0043(6) -0.0019(6) -0.0055(6) C12 0.0179(7) 0.0171(7) 0.0211(8) -0.0019(6) -0.0036(6) -0.0060(6) C13 0.0213(8) 0.0189(8) 0.0292(9) -0.0079(7) 0.0019(7) -0.0066(6) C14 0.0218(8) 0.0228(8) 0.0284(9) -0.0061(7) -0.0006(7) -0.0116(7) C15 0.0164(7) 0.0165(7) 0.0222(8) -0.0028(6) -0.0042(6) -0.0050(6) C16 0.0188(7) 0.0148(7) 0.0220(8) -0.0011(6) -0.0031(6) -0.0073(6) C17 0.0196(8) 0.0188(8) 0.0260(9) -0.0030(7) -0.0063(7) -0.0053(6) C18 0.0259(9) 0.0333(10) 0.0346(11) -0.0132(9) -0.0005(8) 0.0000(8) C19 0.0201(8) 0.0192(8) 0.0254(9) -0.0040(7) -0.0027(7) -0.0041(6) C20 0.0199(8) 0.0164(7) 0.0214(8) -0.0022(6) -0.0023(6) -0.0066(6) C21 0.0210(8) 0.0229(8) 0.0222(8) -0.0063(7) -0.0018(7) -0.0065(7) C22 0.0564(14) 0.0227(10) 0.0552(15) -0.0061(9) -0.0268(12) -0.0095(10) C23 0.078(2) 0.0351(12) 0.0729(19) -0.0163(12) -0.0347(16) -0.0221(13) C24 0.0405(12) 0.0529(14) 0.0413(13) -0.0164(11) -0.0143(10) -0.0172(11) C25 0.0253(9) 0.0425(11) 0.0259(10) -0.0004(8) -0.0064(8) -0.0126(8) C26 0.0228(8) 0.0270(9) 0.0275(9) -0.0019(7) -0.0031(7) -0.0103(7) N1 0.0198(7) 0.0248(7) 0.0217(7) -0.0001(6) -0.0051(6) -0.0087(6) C27 0.0280(9) 0.0283(9) 0.0299(10) 0.0033(8) -0.0080(8) -0.0095(8) C28 0.0310(10) 0.0335(11) 0.0348(11) 0.0040(9) -0.0142(9) -0.0024(8) C29 0.0210(9) 0.0480(12) 0.0348(11) -0.0023(9) -0.0112(8) -0.0067(9) C30 0.0231(9) 0.0395(11) 0.0270(10) -0.0029(8) -0.0077(7) -0.0150(8) C31 0.0194(8) 0.0264(8) 0.0187(8) -0.0041(7) -0.0045(6) -0.0088(7) C32 0.0209(8) 0.0235(8) 0.0195(8) -0.0038(6) -0.0030(6) -0.0105(7) C33 0.0340(10) 0.0294(9) 0.0262(9) -0.0062(8) -0.0065(8) -0.0182(8) C34 0.0650(16) 0.0387(12) 0.0470(14) -0.0070(10) -0.0300(12) -0.0257(11) C35 0.0368(10) 0.0214(8) 0.0334(10) -0.0081(8) -0.0046(8) -0.0151(8) C36 0.0252(9) 0.0179(8) 0.0309(10) -0.0049(7) -0.0016(7) -0.0087(7) C37 0.0351(11) 0.0177(8) 0.0521(13) -0.0008(8) -0.0110(10) -0.0087(8) C38 0.0179(7) 0.0181(7) 0.0226(8) -0.0040(6) -0.0017(6) -0.0073(6) C39 0.0203(8) 0.0149(7) 0.0224(8) 0.0003(6) -0.0058(6) -0.0060(6) C40 0.0212(8) 0.0173(8) 0.0296(9) -0.0008(7) -0.0050(7) -0.0038(6) C41 0.0196(8) 0.0269(9) 0.0314(10) 0.0036(8) -0.0099(7) -0.0054(7) C42 0.0267(9) 0.0396(11) 0.0287(10) -0.0058(8) -0.0112(8) -0.0109(8) C43 0.0262(9) 0.0378(11) 0.0288(10) -0.0132(8) -0.0061(8) -0.0076(8) N2 0.0184(6) 0.0177(6) 0.0199(7) -0.0036(5) -0.0038(5) -0.0072(5) N3 0.0203(7) 0.0264(8) 0.0254(8) -0.0065(6) -0.0047(6) -0.0054(6) N4 0.0167(6) 0.0174(6) 0.0237(7) -0.0020(5) -0.0051(5) -0.0055(5) N5 0.0172(6) 0.0147(6) 0.0244(7) -0.0055(5) -0.0017(5) -0.0062(5) N6 0.0141(6) 0.0195(7) 0.0236(7) -0.0053(6) -0.0029(5) -0.0042(5) O1 0.0282(7) 0.0261(7) 0.0332(8) -0.0008(6) -0.0089(6) 0.0041(6) O2 0.0233(7) 0.0397(8) 0.0398(8) -0.0033(7) -0.0005(6) -0.0166(6) O3 0.0332(8) 0.0211(7) 0.0540(10) 0.0036(6) -0.0078(7) -0.0113(6) O4 0.0402(8) 0.0439(9) 0.0379(8) -0.0205(7) -0.0053(7) -0.0179(7) O5 0.0259(7) 0.0416(8) 0.0462(9) 0.0046(7) -0.0164(7) -0.0081(6) O6 0.0279(7) 0.0438(9) 0.0475(9) -0.0215(7) 0.0089(7) -0.0090(7) C44 0.0513(14) 0.0259(10) 0.0459(13) -0.0084(9) -0.0286(11) 0.0005(9) Cl1 0.0441(3) 0.0513(3) 0.0507(4) -0.0007(3) -0.0210(3) -0.0119(3) Cl2 0.0398(3) 0.0474(3) 0.0715(4) -0.0128(3) -0.0184(3) -0.0050(3) Cl3 0.1097(7) 0.0558(4) 0.0459(4) -0.0065(3) -0.0452(4) -0.0028(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4458(14) . ? S1 O1 1.4499(14) . ? S1 C17 1.7189(18) . ? S1 C19 1.7401(18) . ? S2 O5 1.4460(15) . ? S2 O6 1.4477(15) . ? S2 C10 1.7185(18) . ? S2 C8 1.7362(19) . ? S3 O4 1.4390(14) . ? S3 O3 1.4448(15) . ? S3 C14 1.7184(18) . ? S3 C13 1.7205(18) . ? C1 C2 1.389(3) . ? C1 C6 1.396(2) . ? C1 H1 0.9500 . ? C2 C3 1.380(3) . ? C2 H2 0.9500 . ? C3 C4 1.386(3) . ? C3 H3 0.9500 . ? C4 C5 1.389(3) . ? C4 H4 0.9500 . ? C5 C6 1.390(3) . ? C5 H5 0.9500 . ? C6 C7 1.489(2) . ? C7 C8 1.356(2) . ? C7 N4 1.388(2) . ? C8 C9 1.513(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.352(2) . ? C10 H10 0.9500 . ? C11 N4 1.362(2) . ? C11 C12 1.490(2) . ? C12 C13 1.351(2) . ? C12 N5 1.366(2) . ? C13 H13 0.9500 . ? C14 C15 1.350(2) . ? C14 H14 0.9500 . ? C15 N5 1.371(2) . ? C15 C16 1.493(2) . ? C16 C17 1.351(2) . ? C16 N6 1.368(2) . ? C17 H17 0.9500 . ? C18 C19 1.507(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.360(2) . ? C20 N6 1.378(2) . ? C20 C21 1.492(2) . ? C21 C22 1.385(3) . ? C21 C26 1.394(3) . ? C22 C23 1.393(3) . ? C22 H22 0.9500 . ? C23 C24 1.375(4) . ? C23 H23 0.9500 . ? C24 C25 1.383(3) . ? C24 H24 0.9500 . ? C25 C26 1.387(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? N1 C27 1.334(2) . ? N1 C31 1.353(2) . ? C27 C28 1.383(3) . ? C27 H27 0.9500 . ? C28 C29 1.380(3) . ? C28 H28 0.9500 . ? C29 C30 1.388(3) . ? C29 H29 0.9500 . ? C30 C31 1.387(2) . ? C30 H30 0.9500 . ? C31 C32 1.490(2) . ? C32 N2 1.348(2) . ? C32 C33 1.404(2) . ? C33 C35 1.389(3) . ? C33 C34 1.516(3) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 C36 1.394(3) . ? C35 H35 0.9500 . ? C36 C38 1.403(2) . ? C36 C37 1.509(3) . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 N2 1.342(2) . ? C38 C39 1.493(2) . ? C39 N3 1.348(2) . ? C39 C40 1.389(2) . ? C40 C41 1.388(2) . ? C40 H40 0.9500 . ? C41 C42 1.375(3) . ? C41 H41 0.9500 . ? C42 C43 1.390(3) . ? C42 H42 0.9500 . ? C43 N3 1.346(2) . ? C43 H43 0.9500 . ? N4 H4A 0.8800 . ? N5 H5A 0.8800 . ? N6 H6 0.8800 . ? C44 Cl1 1.754(2) . ? C44 Cl3 1.760(2) . ? C44 Cl2 1.771(3) . ? C44 H44 1.0000 . ? 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 113.89(9) . . ? O2 S1 C17 109.32(9) . . ? O1 S1 C17 110.39(9) . . ? O2 S1 C19 109.67(9) . . ? O1 S1 C19 110.07(8) . . ? C17 S1 C19 102.95(8) . . ? O5 S2 O6 115.23(10) . . ? O5 S2 C10 110.83(9) . . ? O6 S2 C10 108.76(9) . . ? O5 S2 C8 109.91(9) . . ? O6 S2 C8 108.96(10) . . ? C10 S2 C8 102.36(9) . . ? O4 S3 O3 114.76(9) . . ? O4 S3 C14 110.93(9) . . ? O3 S3 C14 108.65(9) . . ? O4 S3 C13 110.25(9) . . ? O3 S3 C13 109.85(9) . . ? C14 S3 C13 101.59(8) . . ? C2 C1 C6 120.26(19) . . ? C2 C1 H1 119.9 . . ? C6 C1 H1 119.9 . . ? C3 C2 C1 120.24(19) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 119.87(19) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 120.2(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 120.29(18) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 119.11(17) . . ? C5 C6 C7 119.63(15) . . ? C1 C6 C7 121.19(17) . . ? C8 C7 N4 123.39(16) . . ? C8 C7 C6 123.46(15) . . ? N4 C7 C6 113.16(14) . . ? C7 C8 C9 125.63(17) . . ? C7 C8 S2 121.54(13) . . ? C9 C8 S2 112.62(14) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 S2 121.86(14) . . ? C11 C10 H10 119.1 . . ? S2 C10 H10 119.1 . . ? C10 C11 N4 124.12(16) . . ? C10 C11 C12 119.04(15) . . ? N4 C11 C12 116.77(14) . . ? C13 C12 N5 124.41(15) . . ? C13 C12 C11 119.80(15) . . ? N5 C12 C11 115.77(14) . . ? C12 C13 S3 123.34(14) . . ? C12 C13 H13 118.3 . . ? S3 C13 H13 118.3 . . ? C15 C14 S3 123.59(14) . . ? C15 C14 H14 118.2 . . ? S3 C14 H14 118.2 . . ? C14 C15 N5 124.08(16) . . ? C14 C15 C16 120.20(15) . . ? N5 C15 C16 115.60(13) . . ? C17 C16 N6 123.98(16) . . ? C17 C16 C15 121.21(15) . . ? N6 C16 C15 114.75(14) . . ? C16 C17 S1 123.33(14) . . ? C16 C17 H17 118.3 . . ? S1 C17 H17 118.3 . . ? C19 C18 H18A 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C19 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C18 124.77(17) . . ? C20 C19 S1 121.54(14) . . ? C18 C19 S1 113.66(13) . . ? C19 C20 N6 124.70(16) . . ? C19 C20 C21 122.10(15) . . ? N6 C20 C21 113.19(14) . . ? C22 C21 C26 118.96(17) . . ? C22 C21 C20 120.95(17) . . ? C26 C21 C20 120.04(15) . . ? C21 C22 C23 120.0(2) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C24 C23 C22 120.7(2) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C25 119.65(19) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 120.0(2) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 120.63(18) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? C27 N1 C31 118.22(15) . . ? N1 C27 C28 123.66(19) . . ? N1 C27 H27 118.2 . . ? C28 C27 H27 118.2 . . ? C29 C28 C27 117.97(19) . . ? C29 C28 H28 121.0 . . ? C27 C28 H28 121.0 . . ? C28 C29 C30 119.39(18) . . ? C28 C29 H29 120.3 . . ? C30 C29 H29 120.3 . . ? C31 C30 C29 119.15(18) . . ? C31 C30 H30 120.4 . . ? C29 C30 H30 120.4 . . ? N1 C31 C30 121.61(17) . . ? N1 C31 C32 114.84(14) . . ? C30 C31 C32 123.48(16) . . ? N2 C32 C33 121.49(16) . . ? N2 C32 C31 113.46(14) . . ? C33 C32 C31 125.03(15) . . ? C35 C33 C32 117.07(16) . . ? C35 C33 C34 119.92(17) . . ? C32 C33 C34 123.01(18) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 C36 122.44(16) . . ? C33 C35 H35 118.8 . . ? C36 C35 H35 118.8 . . ? C35 C36 C38 116.18(17) . . ? C35 C36 C37 120.85(16) . . ? C38 C36 C37 122.91(17) . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? N2 C38 C36 122.52(15) . . ? N2 C38 C39 113.81(14) . . ? C36 C38 C39 123.66(16) . . ? N3 C39 C40 122.93(15) . . ? N3 C39 C38 115.34(14) . . ? C40 C39 C38 121.59(15) . . ? C41 C40 C39 118.72(17) . . ? C41 C40 H40 120.6 . . ? C39 C40 H40 120.6 . . ? C42 C41 C40 119.15(17) . . ? C42 C41 H41 120.4 . . ? C40 C41 H41 120.4 . . ? C41 C42 C43 118.63(17) . . ? C41 C42 H42 120.7 . . ? C43 C42 H42 120.7 . . ? N3 C43 C42 123.37(18) . . ? N3 C43 H43 118.3 . . ? C42 C43 H43 118.3 . . ? C38 N2 C32 120.29(14) . . ? C43 N3 C39 117.15(15) . . ? C11 N4 C7 123.48(14) . . ? C11 N4 H4A 118.3 . . ? C7 N4 H4A 118.3 . . ? C12 N5 C15 122.68(14) . . ? C12 N5 H5A 118.7 . . ? C15 N5 H5A 118.7 . . ? C16 N6 C20 123.48(14) . . ? C16 N6 H6 118.3 . . ? C20 N6 H6 118.3 . . ? Cl1 C44 Cl3 109.92(14) . . ? Cl1 C44 Cl2 110.44(12) . . ? Cl3 C44 Cl2 109.62(12) . . ? Cl1 C44 H44 108.9 . . ? Cl3 C44 H44 108.9 . . ? Cl2 C44 H44 108.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.3(3) . . . . ? C1 C2 C3 C4 -0.7(4) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? C4 C5 C6 C7 176.39(19) . . . . ? C2 C1 C6 C5 0.3(3) . . . . ? C2 C1 C6 C7 -176.60(18) . . . . ? C5 C6 C7 C8 130.7(2) . . . . ? C1 C6 C7 C8 -52.4(3) . . . . ? C5 C6 C7 N4 -49.7(2) . . . . ? C1 C6 C7 N4 127.22(18) . . . . ? N4 C7 C8 C9 -179.76(18) . . . . ? C6 C7 C8 C9 -0.2(3) . . . . ? N4 C7 C8 S2 5.8(3) . . . . ? C6 C7 C8 S2 -174.63(13) . . . . ? O5 S2 C8 C7 -134.52(16) . . . . ? O6 S2 C8 C7 98.33(17) . . . . ? C10 S2 C8 C7 -16.71(18) . . . . ? O5 S2 C8 C9 50.39(17) . . . . ? O6 S2 C8 C9 -76.76(16) . . . . ? C10 S2 C8 C9 168.20(15) . . . . ? O5 S2 C10 C11 135.37(16) . . . . ? O6 S2 C10 C11 -96.97(17) . . . . ? C8 S2 C10 C11 18.22(18) . . . . ? S2 C10 C11 N4 -8.9(3) . . . . ? S2 C10 C11 C12 174.18(13) . . . . ? C10 C11 C12 C13 -50.8(2) . . . . ? N4 C11 C12 C13 132.07(18) . . . . ? C10 C11 C12 N5 127.54(18) . . . . ? N4 C11 C12 N5 -49.6(2) . . . . ? N5 C12 C13 S3 -2.8(3) . . . . ? C11 C12 C13 S3 175.38(13) . . . . ? O4 S3 C13 C12 123.00(17) . . . . ? O3 S3 C13 C12 -109.56(17) . . . . ? C14 S3 C13 C12 5.34(19) . . . . ? O4 S3 C14 C15 -123.36(17) . . . . ? O3 S3 C14 C15 109.60(17) . . . . ? C13 S3 C14 C15 -6.18(19) . . . . ? S3 C14 C15 N5 4.5(3) . . . . ? S3 C14 C15 C16 -171.40(13) . . . . ? C14 C15 C16 C17 -47.3(2) . . . . ? N5 C15 C16 C17 136.48(17) . . . . ? C14 C15 C16 N6 129.98(17) . . . . ? N5 C15 C16 N6 -46.3(2) . . . . ? N6 C16 C17 S1 -0.6(3) . . . . ? C15 C16 C17 S1 176.35(13) . . . . ? O2 S1 C17 C16 -116.28(16) . . . . ? O1 S1 C17 C16 117.69(16) . . . . ? C19 S1 C17 C16 0.24(18) . . . . ? O2 S1 C19 C20 117.23(16) . . . . ? O1 S1 C19 C20 -116.72(16) . . . . ? C17 S1 C19 C20 0.97(17) . . . . ? O2 S1 C19 C18 -60.92(16) . . . . ? O1 S1 C19 C18 65.13(16) . . . . ? C17 S1 C19 C18 -177.19(14) . . . . ? C18 C19 C20 N6 176.00(17) . . . . ? S1 C19 C20 N6 -1.9(3) . . . . ? C18 C19 C20 C21 -2.4(3) . . . . ? S1 C19 C20 C21 179.64(13) . . . . ? C19 C20 C21 C22 -63.9(3) . . . . ? N6 C20 C21 C22 117.6(2) . . . . ? C19 C20 C21 C26 118.8(2) . . . . ? N6 C20 C21 C26 -59.7(2) . . . . ? C26 C21 C22 C23 -0.1(4) . . . . ? C20 C21 C22 C23 -177.4(2) . . . . ? C21 C22 C23 C24 0.0(4) . . . . ? C22 C23 C24 C25 -0.2(4) . . . . ? C23 C24 C25 C26 0.5(4) . . . . ? C24 C25 C26 C21 -0.5(3) . . . . ? C22 C21 C26 C25 0.3(3) . . . . ? C20 C21 C26 C25 177.66(17) . . . . ? C31 N1 C27 C28 -0.4(3) . . . . ? N1 C27 C28 C29 0.3(3) . . . . ? C27 C28 C29 C30 0.0(3) . . . . ? C28 C29 C30 C31 -0.2(3) . . . . ? C27 N1 C31 C30 0.2(3) . . . . ? C27 N1 C31 C32 177.12(16) . . . . ? C29 C30 C31 N1 0.1(3) . . . . ? C29 C30 C31 C32 -176.56(17) . . . . ? N1 C31 C32 N2 -41.0(2) . . . . ? C30 C31 C32 N2 135.93(18) . . . . ? N1 C31 C32 C33 137.83(18) . . . . ? C30 C31 C32 C33 -45.3(3) . . . . ? N2 C32 C33 C35 0.2(3) . . . . ? C31 C32 C33 C35 -178.50(17) . . . . ? N2 C32 C33 C34 179.37(19) . . . . ? C31 C32 C33 C34 0.7(3) . . . . ? C32 C33 C35 C36 -0.2(3) . . . . ? C34 C33 C35 C36 -179.4(2) . . . . ? C33 C35 C36 C38 -0.2(3) . . . . ? C33 C35 C36 C37 -177.50(19) . . . . ? C35 C36 C38 N2 0.7(3) . . . . ? C37 C36 C38 N2 177.96(18) . . . . ? C35 C36 C38 C39 -179.15(17) . . . . ? C37 C36 C38 C39 -1.9(3) . . . . ? N2 C38 C39 N3 -50.9(2) . . . . ? C36 C38 C39 N3 128.92(18) . . . . ? N2 C38 C39 C40 124.93(17) . . . . ? C36 C38 C39 C40 -55.2(2) . . . . ? N3 C39 C40 C41 -0.2(3) . . . . ? C38 C39 C40 C41 -175.77(16) . . . . ? C39 C40 C41 C42 -1.6(3) . . . . ? C40 C41 C42 C43 1.8(3) . . . . ? C41 C42 C43 N3 -0.3(3) . . . . ? C36 C38 N2 C32 -0.8(3) . . . . ? C39 C38 N2 C32 179.10(15) . . . . ? C33 C32 N2 C38 0.3(3) . . . . ? C31 C32 N2 C38 179.13(15) . . . . ? C42 C43 N3 C39 -1.4(3) . . . . ? C40 C39 N3 C43 1.7(3) . . . . ? C38 C39 N3 C43 177.49(16) . . . . ? C10 C11 N4 C7 -6.7(3) . . . . ? C12 C11 N4 C7 170.29(15) . . . . ? C8 C7 N4 C11 8.3(3) . . . . ? C6 C7 N4 C11 -171.32(15) . . . . ? C13 C12 N5 C15 -0.5(3) . . . . ? C11 C12 N5 C15 -178.68(15) . . . . ? C14 C15 N5 C12 -0.5(3) . . . . ? C16 C15 N5 C12 175.64(15) . . . . ? C17 C16 N6 C20 -0.2(3) . . . . ? C15 C16 N6 C20 -177.37(15) . . . . ? C19 C20 N6 C16 1.6(3) . . . . ? C21 C20 N6 C16 -179.85(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 31.06 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.810 _refine_diff_density_min -0.856 _refine_diff_density_rms 0.065 # Attachment 'CCDC783460.cif' data_08125b _database_code_depnum_ccdc_archive 'CCDC 783460' #TrackingRef 'CCDC783460.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H19 N3 O2 S' _chemical_formula_sum 'C22 H19 N3 O2 S' _chemical_formula_weight 389.46 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.937(6) _cell_length_b 6.7394(13) _cell_length_c 9.871(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.11(3) _cell_angle_gamma 90.00 _cell_volume 1857.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 14980 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 25.03 _exptl_crystal_description petal _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9074 _exptl_absorpt_correction_T_max 0.9853 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6382 _diffrn_reflns_av_R_equivalents 0.054 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.43 _reflns_number_total 1657 _reflns_number_gt 1339 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Nonius, 1997-2001)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.0665P)^2^+2.2606P] 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 1657 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1289 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 O1 O 0.48221(6) 0.0183(2) 0.63795(16) 0.0337(4) Uani 1 1 d . . . S2 S 0.5000 0.14016(11) 0.7500 0.0271(3) Uani 1 2 d S . . C3 C 0.45680(8) 0.2983(3) 0.8003(2) 0.0320(6) Uani 1 1 d . . . H3A H 0.4286 0.2427 0.8356 0.038 Uiso 1 1 calc R . . C4 C 0.45995(8) 0.4989(3) 0.7934(2) 0.0285(5) Uani 1 1 d . . . N5 N 0.5000 0.5943(4) 0.7500 0.0333(7) Uani 1 2 d S . . H5A H 0.5000 0.7249 0.7500 0.040 Uiso 1 2 calc SR . . C6 C 0.41954(8) 0.6213(3) 0.8333(2) 0.0272(5) Uani 1 1 d . . . N7 N 0.42611(6) 0.7914(3) 0.91146(19) 0.0287(5) Uani 1 1 d . . . H7A H 0.4539 0.8389 0.9411 0.034 Uiso 1 1 calc R . . C8 C 0.38208(8) 0.8732(3) 0.9349(2) 0.0274(5) Uani 1 1 d . . . C9 C 0.34729(8) 0.7545(3) 0.8668(2) 0.0285(5) Uani 1 1 d . . . C10 C 0.37149(8) 0.5939(3) 0.8033(2) 0.0283(5) Uani 1 1 d . . . C11 C 0.34786(9) 0.4337(4) 0.7193(3) 0.0394(6) Uani 1 1 d . . . H11A H 0.3694 0.3916 0.6486 0.059 Uiso 1 1 calc R . . H11B H 0.3180 0.4846 0.6771 0.059 Uiso 1 1 calc R . . H11C H 0.3407 0.3203 0.7773 0.059 Uiso 1 1 calc R . . C12 C 0.37044(8) 1.0371(4) 1.0123(2) 0.0327(6) Uani 1 1 d . . . H12A H 0.3943 1.1132 1.0595 0.039 Uiso 1 1 calc R . . C13 C 0.32236(9) 1.0840(4) 1.0172(3) 0.0391(6) Uani 1 1 d . . . H13A H 0.3130 1.1950 1.0693 0.047 Uiso 1 1 calc R . . C14 C 0.28728(9) 0.9732(4) 0.9478(3) 0.0397(6) Uani 1 1 d . . . H14A H 0.2547 1.0123 0.9517 0.048 Uiso 1 1 calc R . . C15 C 0.29880(8) 0.8081(4) 0.8736(2) 0.0344(6) Uani 1 1 d . . . H15A H 0.2745 0.7321 0.8279 0.041 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 O1 0.0345(9) 0.0285(9) 0.0377(10) -0.0053(7) -0.0034(7) 0.0022(7) S2 0.0276(4) 0.0198(4) 0.0341(5) 0.000 0.0021(3) 0.000 C3 0.0275(12) 0.0238(12) 0.0455(15) 0.0002(10) 0.0095(10) -0.0015(10) C4 0.0257(12) 0.0270(12) 0.0328(13) -0.0020(9) 0.0020(9) -0.0005(10) N5 0.0269(14) 0.0175(13) 0.0561(19) 0.000 0.0089(13) 0.000 C6 0.0290(12) 0.0201(12) 0.0326(12) 0.0004(9) 0.0040(9) 0.0004(10) N7 0.0226(10) 0.0235(10) 0.0398(11) -0.0034(9) 0.0004(8) -0.0003(8) C8 0.0271(12) 0.0263(12) 0.0291(12) 0.0038(10) 0.0043(9) 0.0024(10) C9 0.0281(12) 0.0279(13) 0.0295(12) 0.0041(10) 0.0024(9) 0.0002(10) C10 0.0284(12) 0.0258(12) 0.0307(12) -0.0009(10) 0.0020(9) -0.0011(10) C11 0.0376(14) 0.0337(14) 0.0464(15) -0.0064(12) -0.0047(11) -0.0041(12) C12 0.0315(13) 0.0314(13) 0.0354(13) -0.0037(11) 0.0022(10) 0.0022(11) C13 0.0403(15) 0.0372(14) 0.0404(15) -0.0022(12) 0.0083(11) 0.0076(12) C14 0.0271(13) 0.0475(16) 0.0448(15) -0.0005(13) 0.0051(11) 0.0096(12) C15 0.0260(12) 0.0403(14) 0.0368(13) 0.0009(11) 0.0005(10) -0.0001(11) _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 O1 S2 1.4506(16) . ? S2 O1 1.4506(16) 2_656 ? S2 C3 1.698(2) 2_656 ? S2 C3 1.698(2) . ? C3 C4 1.357(3) . ? C3 H3A 0.9500 . ? C4 N5 1.373(3) . ? C4 C6 1.464(3) . ? N5 C4 1.373(3) 2_656 ? N5 H5A 0.8800 . ? C6 C10 1.376(3) . ? C6 N7 1.390(3) . ? N7 C8 1.375(3) . ? N7 H7A 0.8800 . ? C8 C12 1.388(3) . ? C8 C9 1.410(3) . ? C9 C15 1.406(3) . ? C9 C10 1.433(3) . ? C10 C11 1.500(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.382(3) . ? C12 H12A 0.9500 . ? C13 C14 1.392(4) . ? C13 H13A 0.9500 . ? C14 C15 1.377(4) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? 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 S2 O1 111.06(14) 2_656 . ? O1 S2 C3 110.55(10) 2_656 2_656 ? O1 S2 C3 111.07(11) . 2_656 ? O1 S2 C3 111.07(11) 2_656 . ? O1 S2 C3 110.55(10) . . ? C3 S2 C3 102.24(16) 2_656 . ? C4 C3 S2 124.25(18) . . ? C4 C3 H3A 117.9 . . ? S2 C3 H3A 117.9 . . ? C3 C4 N5 122.5(2) . . ? C3 C4 C6 119.7(2) . . ? N5 C4 C6 117.7(2) . . ? C4 N5 C4 124.2(3) . 2_656 ? C4 N5 H5A 117.9 . . ? C4 N5 H5A 117.9 2_656 . ? C10 C6 N7 109.8(2) . . ? C10 C6 C4 128.5(2) . . ? N7 C6 C4 121.78(19) . . ? C8 N7 C6 108.86(18) . . ? C8 N7 H7A 125.6 . . ? C6 N7 H7A 125.6 . . ? N7 C8 C12 129.8(2) . . ? N7 C8 C9 107.30(19) . . ? C12 C8 C9 122.8(2) . . ? C15 C9 C8 118.7(2) . . ? C15 C9 C10 133.3(2) . . ? C8 C9 C10 108.00(19) . . ? C6 C10 C9 106.1(2) . . ? C6 C10 C11 128.4(2) . . ? C9 C10 C11 125.5(2) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C8 116.7(2) . . ? C13 C12 H12A 121.7 . . ? C8 C12 H12A 121.7 . . ? C12 C13 C14 121.8(2) . . ? C12 C13 H13A 119.1 . . ? C14 C13 H13A 119.1 . . ? C15 C14 C13 121.4(2) . . ? C15 C14 H14A 119.3 . . ? C13 C14 H14A 119.3 . . ? C14 C15 C9 118.5(2) . . ? C14 C15 H15A 120.7 . . ? C9 C15 H15A 120.7 . . ? 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 O1 S2 C3 C4 119.4(2) 2_656 . . . ? O1 S2 C3 C4 -116.8(2) . . . . ? C3 S2 C3 C4 1.48(17) 2_656 . . . ? S2 C3 C4 N5 -3.1(4) . . . . ? S2 C3 C4 C6 176.96(16) . . . . ? C3 C4 N5 C4 1.58(18) . . . 2_656 ? C6 C4 N5 C4 -178.4(2) . . . 2_656 ? C3 C4 C6 C10 -43.1(4) . . . . ? N5 C4 C6 C10 136.9(2) . . . . ? C3 C4 C6 N7 137.0(2) . . . . ? N5 C4 C6 N7 -43.0(3) . . . . ? C10 C6 N7 C8 1.2(3) . . . . ? C4 C6 N7 C8 -178.9(2) . . . . ? C6 N7 C8 C12 176.7(2) . . . . ? C6 N7 C8 C9 -1.6(2) . . . . ? N7 C8 C9 C15 -179.31(19) . . . . ? C12 C8 C9 C15 2.3(3) . . . . ? N7 C8 C9 C10 1.4(2) . . . . ? C12 C8 C9 C10 -177.1(2) . . . . ? N7 C6 C10 C9 -0.3(3) . . . . ? C4 C6 C10 C9 179.8(2) . . . . ? N7 C6 C10 C11 178.4(2) . . . . ? C4 C6 C10 C11 -1.4(4) . . . . ? C15 C9 C10 C6 -179.8(2) . . . . ? C8 C9 C10 C6 -0.6(3) . . . . ? C15 C9 C10 C11 1.4(4) . . . . ? C8 C9 C10 C11 -179.4(2) . . . . ? N7 C8 C12 C13 -179.8(2) . . . . ? C9 C8 C12 C13 -1.8(3) . . . . ? C8 C12 C13 C14 -0.2(4) . . . . ? C12 C13 C14 C15 1.7(4) . . . . ? C13 C14 C15 C9 -1.2(4) . . . . ? C8 C9 C15 C14 -0.7(3) . . . . ? C10 C9 C15 C14 178.4(2) . . . . ? 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 N5 H5A O1 0.88 2.31 3.098(3) 148.8 2_666 N5 H5A O1 0.88 2.31 3.098(3) 148.8 1_565 N5 H5A S2 0.88 2.80 3.679(3) 180.0 1_565 N7 H7A O1 0.88 2.28 2.973(3) 135.2 6_566 N7 H7A O1 0.88 2.32 3.038(2) 139.5 2_666 _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.43 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.245 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.059