# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Marina Fonari' _publ_contact_author_email FONARI.XRAY@PHYS.ASM.MD _publ_section_title ; From chains to ladders in molecular complexes with 2,3-thiophene-15-crown-5, 2,3-naphtho-15-crown-5, and bis-(18-crown-6)-stilbene constructed by weak hydrogen bondings ; loop_ _publ_author_name 'Marina Fonari' 'Stepan S. Basok' 'Mark Botoshansky' 'Edward V Ganin' 'Arkadii A Yavolovskii' # Attachment 'bas1c.cif' data_bas1c _database_code_depnum_ccdc_archive 'CCDC 771037' #TrackingRef 'bas1c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 18,18'-(E)-ethene-1,2-diylbis-2,3,5,6,8,9,11,12,14,15-decahydro- 1,4,7,10,13,16-benzohexaoxacyclooctadecine bis(ethanedithioamide) clathrate ; _chemical_name_common ; 18,18'-(E)-ethene-1,2-diylbis-2,3,5,6,8,9,11,12,14,15- decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecine bis(ethanedithioamide) clathrate ; _chemical_melting_point ? _chemical_formula_moiety 'C34 H48 O12, 2(C2 H4 N2 S2)' _chemical_formula_sum 'C38 H56 N4 O12 S4' _chemical_formula_weight 889.11 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7140(15) _cell_length_b 9.760(2) _cell_length_c 15.675(3) _cell_angle_alpha 90.12(2) _cell_angle_beta 96.87(3) _cell_angle_gamma 107.23(3) _cell_volume 1118.2(4) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6136 _cell_measurement_theta_min 1.31 _cell_measurement_theta_max 24.68 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.274 _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 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 'Nonius KappaCCD' _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 6161 _diffrn_reflns_av_R_equivalents 0.0883 _diffrn_reflns_av_sigmaI/netI 0.1882 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 24.68 _reflns_number_total 3234 _reflns_number_gt 997 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics MERCURY _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. The minor component of the crown ether was refined using the SAME restraints to make equivalent bond distances and bond angles in two crown molecules equal. SADI restraints were applied to the N-H distances in amino-groups. ; _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^)+(0.0011P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3234 _refine_ls_number_parameters 401 _refine_ls_number_restraints 54 _refine_ls_R_factor_all 0.2223 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0788 _refine_ls_goodness_of_fit_ref 0.772 _refine_ls_restrained_S_all 0.777 _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 0.6403(4) 0.1009(3) 0.3378(3) 0.1200(14) Uani 0.792(4) 1 d P A 1 S2 S 0.7365(4) 0.5201(3) 0.2374(2) 0.1131(11) Uani 0.792(4) 1 d P A 1 N1 N 0.4446(10) 0.2647(13) 0.2550(7) 0.099(3) Uani 0.792(4) 1 d PD A 1 H1N1 H 0.407(8) 0.326(6) 0.225(4) 0.148 Uiso 0.792(4) 1 d PD A 1 H2N1 H 0.367(7) 0.186(6) 0.265(4) 0.148 Uiso 0.792(4) 1 d PD A 1 N2 N 0.9213(15) 0.3151(11) 0.2832(8) 0.111(4) Uani 0.792(4) 1 d PD A 1 H1N2 H 0.991(8) 0.254(6) 0.311(4) 0.167 Uiso 0.792(4) 1 d PD A 1 H2N2 H 1.010(8) 0.398(6) 0.261(5) 0.167 Uiso 0.792(4) 1 d PD A 1 C18 C 0.6140(14) 0.2473(10) 0.2885(5) 0.124(3) Uani 0.792(4) 1 d P A 1 C19 C 0.7609(13) 0.3631(9) 0.2629(5) 0.118(3) Uani 0.792(4) 1 d P A 1 S1A S 0.6830(14) 0.1774(12) 0.3807(7) 0.075(3) Uani 0.208(4) 1 d P A 2 S2A S 0.7376(17) 0.4645(16) 0.1784(9) 0.129(5) Uani 0.208(4) 1 d P A 2 N1A N 0.486(7) 0.314(5) 0.282(3) 0.110(18) Uiso 0.208(4) 1 d P A 2 N2A N 0.952(6) 0.364(5) 0.286(3) 0.078(12) Uiso 0.208(4) 1 d P A 2 C18A C 0.764(2) 0.2514(17) 0.3035(11) 0.014(4) Uiso 0.208(4) 1 d P A 2 C19A C 0.630(3) 0.351(2) 0.2595(11) 0.016(5) Uiso 0.208(4) 1 d P A 2 O1 O 0.2723(6) 0.5874(5) 0.2351(4) 0.0780(15) Uani 0.792(4) 1 d PD A 1 O2 O 0.3012(7) 0.4970(8) 0.4044(4) 0.102(2) Uani 0.792(4) 1 d PD A 1 O3 O 0.1633(10) 0.1905(10) 0.4299(6) 0.123(3) Uani 0.792(4) 1 d PD A 1 O4 O 0.1173(11) -0.0046(10) 0.2912(7) 0.167(4) Uani 0.792(4) 1 d PD A 1 O5 O 0.0746(10) 0.1002(10) 0.1277(5) 0.154(3) Uani 0.792(4) 1 d PD A 1 O6 O 0.1951(7) 0.3943(6) 0.1124(4) 0.0901(17) Uani 0.792(4) 1 d PD A 1 C1 C 0.4918(9) 0.9702(11) 0.0357(7) 0.080(3) Uani 0.792(4) 1 d PD . 1 H1 H 0.5252 1.0319 0.0841 0.096 Uiso 0.792(4) 1 calc PR A 1 C2 C 0.4272(17) 0.8162(12) 0.0525(9) 0.084(4) Uani 0.792(4) 1 d PD A 1 C3 C 0.3961(7) 0.7754(8) 0.1358(5) 0.077(2) Uani 0.792(4) 1 d PD A 1 H3 H 0.4335 0.8462 0.1797 0.093 Uiso 0.792(4) 1 calc PR A 1 C4 C 0.314(2) 0.6380(11) 0.1567(8) 0.069(4) Uani 0.792(4) 1 d PD A 1 C5 C 0.2774(7) 0.5299(9) 0.0890(6) 0.076(2) Uani 0.792(4) 1 d PD A 1 C6 C 0.3190(8) 0.5657(8) 0.0061(5) 0.093(2) Uani 0.792(4) 1 d PD A 1 H6 H 0.2955 0.4952 -0.0373 0.112 Uiso 0.792(4) 1 calc PR A 1 C7 C 0.3970(8) 0.7106(9) -0.0099(5) 0.088(2) Uani 0.792(4) 1 d PD A 1 H7 H 0.4291 0.7358 -0.0643 0.106 Uiso 0.792(4) 1 calc PR A 1 C8 C 0.3420(10) 0.6863(7) 0.3081(5) 0.088(3) Uani 0.792(4) 1 d PD A 1 H8A H 0.3157 0.7761 0.2961 0.106 Uiso 0.792(4) 1 calc PR A 1 H8B H 0.4735 0.7061 0.3203 0.106 Uiso 0.792(4) 1 calc PR A 1 C9 C 0.2511(12) 0.6194(10) 0.3844(5) 0.095(3) Uani 0.792(4) 1 d PD A 1 H9A H 0.2885 0.6872 0.4333 0.114 Uiso 0.792(4) 1 calc PR A 1 H9B H 0.1192 0.5947 0.3708 0.114 Uiso 0.792(4) 1 calc PR A 1 C10 C 0.2301(11) 0.4253(12) 0.4795(5) 0.128(4) Uani 0.792(4) 1 d PD A 1 H10A H 0.2784 0.4904 0.5293 0.153 Uiso 0.792(4) 1 calc PR A 1 H10B H 0.0981 0.4050 0.4719 0.153 Uiso 0.792(4) 1 calc PR A 1 C11 C 0.2707(16) 0.3008(14) 0.4957(8) 0.187(8) Uani 0.792(4) 1 d PD A 1 H11A H 0.2415 0.2696 0.5523 0.225 Uiso 0.792(4) 1 calc PR A 1 H11B H 0.4003 0.3157 0.4943 0.225 Uiso 0.792(4) 1 calc PR A 1 C12 C 0.2000(18) 0.0592(16) 0.4392(10) 0.188(9) Uani 0.792(4) 1 d PD A 1 H12A H 0.1797 0.0234 0.4960 0.226 Uiso 0.792(4) 1 calc PR A 1 H12B H 0.3258 0.0693 0.4310 0.226 Uiso 0.792(4) 1 calc PR A 1 C13 C 0.0685(15) -0.0424(15) 0.3702(11) 0.168(9) Uani 0.792(4) 1 d PD A 1 H13A H 0.0705 -0.1400 0.3802 0.201 Uiso 0.792(4) 1 calc PR A 1 H13B H -0.0550 -0.0387 0.3730 0.201 Uiso 0.792(4) 1 calc PR A 1 C14 C -0.012(2) -0.0841(15) 0.2206(10) 0.215(8) Uani 0.792(4) 1 d PD A 1 H14A H 0.0297 -0.1646 0.2056 0.258 Uiso 0.792(4) 1 calc PR A 1 H14B H -0.1275 -0.1241 0.2429 0.258 Uiso 0.792(4) 1 calc PR A 1 C15 C -0.043(2) -0.0302(14) 0.1564(10) 0.226(8) Uani 0.792(4) 1 d PD A 1 H15A H -0.1607 -0.0140 0.1584 0.271 Uiso 0.792(4) 1 calc PR A 1 H15B H -0.0614 -0.1024 0.1108 0.271 Uiso 0.792(4) 1 calc PR A 1 C16 C -0.0311(14) 0.1593(14) 0.0801(9) 0.194(8) Uani 0.792(4) 1 d PD A 1 H16A H -0.1163 0.1835 0.1137 0.233 Uiso 0.792(4) 1 calc PR A 1 H16B H -0.1003 0.0943 0.0327 0.233 Uiso 0.792(4) 1 calc PR A 1 C17 C 0.0936(14) 0.2934(11) 0.0467(6) 0.118(3) Uani 0.792(4) 1 d PD A 1 H17A H 0.1778 0.2663 0.0137 0.142 Uiso 0.792(4) 1 calc PR A 1 H17B H 0.0203 0.3382 0.0082 0.142 Uiso 0.792(4) 1 calc PR A 1 O1A O 0.223(3) 0.475(2) 0.1437(14) 0.100(9) Uiso 0.208(4) 1 d PD A 2 O2A O 0.039(3) 0.1618(18) 0.0863(14) 0.046(6) Uiso 0.208(4) 1 d PD A 2 O3A O 0.149(3) -0.027(3) 0.2588(14) 0.068(7) Uiso 0.208(4) 1 d PD A 2 O4A O 0.150(4) 0.126(3) 0.414(2) 0.076(10) Uiso 0.208(4) 1 d PD A 2 O5A O 0.291(4) 0.443(3) 0.433(2) 0.074(8) Uiso 0.208(4) 1 d PD A 2 O6A O 0.285(3) 0.608(3) 0.2895(15) 0.077(9) Uiso 0.208(4) 1 d PD A 2 C1A C 0.488(5) 0.921(3) -0.0006(15) 0.076(15) Uiso 0.208(4) 1 d PD . 2 H1A H 0.4950 0.8737 -0.0508 0.091 Uiso 0.208(4) 1 calc PR A 2 C2A C 0.453(5) 0.842(3) 0.0786(16) 0.028(10) Uiso 0.208(4) 1 d PD A 2 C3A C 0.352(3) 0.697(2) 0.0724(16) 0.072(8) Uiso 0.208(4) 1 d PD A 2 H3A H 0.2994 0.6545 0.0185 0.086 Uiso 0.208(4) 1 calc PR A 2 C4A C 0.329(7) 0.615(3) 0.1435(18) 0.030(12) Uiso 0.208(4) 1 d PD A 2 C5A C 0.351(4) 0.691(2) 0.2254(16) 0.096(12) Uiso 0.208(4) 1 d PD A 2 C6A C 0.437(2) 0.8374(18) 0.2341(12) 0.061(6) Uiso 0.208(4) 1 d PD A 2 H6A H 0.4641 0.8864 0.2872 0.074 Uiso 0.208(4) 1 calc PR A 2 C7A C 0.481(2) 0.907(2) 0.1585(12) 0.067(7) Uiso 0.208(4) 1 d PD A 2 H7A H 0.5332 1.0061 0.1629 0.080 Uiso 0.208(4) 1 calc PR A 2 C8A C 0.140(5) 0.410(3) 0.063(2) 0.16(2) Uiso 0.208(4) 1 d PD A 2 H8A1 H 0.1925 0.4716 0.0183 0.190 Uiso 0.208(4) 1 calc PR A 2 H8A2 H 0.0103 0.4015 0.0572 0.190 Uiso 0.208(4) 1 calc PR A 2 C9A C 0.160(3) 0.265(2) 0.0481(18) 0.060(9) Uiso 0.208(4) 1 d PD A 2 H9A1 H 0.1426 0.2429 -0.0133 0.072 Uiso 0.208(4) 1 calc PR A 2 H9A2 H 0.2833 0.2663 0.0704 0.072 Uiso 0.208(4) 1 calc PR A 2 C10A C 0.110(3) 0.058(2) 0.1254(16) 0.017(5) Uiso 0.208(4) 1 d PD A 2 H10C H 0.1704 0.0331 0.0793 0.020 Uiso 0.208(4) 1 calc PR A 2 H10D H 0.2095 0.1179 0.1655 0.020 Uiso 0.208(4) 1 calc PR A 2 C11A C 0.071(3) -0.064(3) 0.1664(17) 0.080(10) Uiso 0.208(4) 1 d PD A 2 H11C H 0.1253 -0.1305 0.1422 0.096 Uiso 0.208(4) 1 calc PR A 2 H11D H -0.0603 -0.1078 0.1614 0.096 Uiso 0.208(4) 1 calc PR A 2 C12A C 0.050(5) -0.077(4) 0.3259(16) 0.082(15) Uiso 0.208(4) 1 d PD A 2 H12C H 0.0190 -0.1803 0.3279 0.098 Uiso 0.208(4) 1 calc PR A 2 H12D H -0.0620 -0.0494 0.3205 0.098 Uiso 0.208(4) 1 calc PR A 2 C13A C 0.180(5) -0.003(3) 0.4078(19) 0.060(11) Uiso 0.208(4) 1 d PD A 2 H13C H 0.1499 -0.0582 0.4582 0.072 Uiso 0.208(4) 1 calc PR A 2 H13D H 0.3069 0.0082 0.4008 0.072 Uiso 0.208(4) 1 calc PR A 2 C14A C 0.264(5) 0.220(3) 0.485(2) 0.076(12) Uiso 0.208(4) 1 d PD A 2 H14C H 0.2443 0.1708 0.5380 0.091 Uiso 0.208(4) 1 calc PR A 2 H14D H 0.3914 0.2361 0.4768 0.091 Uiso 0.208(4) 1 calc PR A 2 C15A C 0.238(9) 0.333(3) 0.492(3) 0.37(8) Uiso 0.208(4) 1 d PD A 2 H15C H 0.2958 0.3739 0.5481 0.449 Uiso 0.208(4) 1 calc PR A 2 H15D H 0.1070 0.3143 0.4921 0.449 Uiso 0.208(4) 1 calc PR A 2 C16A C 0.232(4) 0.553(3) 0.442(2) 0.128(15) Uiso 0.208(4) 1 d PD A 2 H16C H 0.2656 0.5954 0.5002 0.154 Uiso 0.208(4) 1 calc PR A 2 H16D H 0.1000 0.5287 0.4275 0.154 Uiso 0.208(4) 1 calc PR A 2 C17A C 0.335(4) 0.654(3) 0.3760(17) 0.087(16) Uiso 0.208(4) 1 d PD A 2 H17C H 0.3174 0.7471 0.3826 0.105 Uiso 0.208(4) 1 calc PR A 2 H17D H 0.4651 0.6659 0.3902 0.105 Uiso 0.208(4) 1 calc PR A 2 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 0.0681(16) 0.094(3) 0.210(4) 0.061(2) 0.044(2) 0.0323(16) S2 0.0925(13) 0.084(2) 0.161(3) 0.032(2) 0.017(2) 0.0231(13) N1 0.045(4) 0.128(9) 0.120(8) 0.008(7) -0.011(4) 0.028(4) N2 0.047(5) 0.097(9) 0.180(8) -0.020(7) 0.013(4) 0.008(5) C18 0.152(11) 0.111(9) 0.107(8) 0.006(6) 0.054(7) 0.023(7) C19 0.119(8) 0.098(8) 0.108(8) -0.003(5) -0.004(6) -0.003(6) S1A 0.070(5) 0.082(8) 0.074(7) 0.015(6) 0.002(4) 0.026(5) S2A 0.109(6) 0.142(12) 0.135(12) 0.065(9) 0.013(8) 0.037(7) O1 0.083(3) 0.070(4) 0.071(4) 0.010(4) 0.008(4) 0.009(2) O2 0.089(3) 0.111(6) 0.104(6) 0.037(4) 0.023(3) 0.024(4) O3 0.082(4) 0.111(7) 0.171(8) 0.057(6) 0.009(4) 0.023(5) O4 0.126(5) 0.179(9) 0.175(10) 0.085(8) 0.057(7) -0.001(5) O5 0.141(6) 0.157(8) 0.154(6) 0.017(6) -0.055(5) 0.060(6) O6 0.103(4) 0.078(5) 0.076(5) 0.002(4) 0.002(3) 0.011(4) C1 0.066(4) 0.082(7) 0.087(8) 0.022(7) 0.015(5) 0.014(5) C2 0.049(5) 0.093(10) 0.102(11) 0.025(8) -0.001(8) 0.011(6) C3 0.058(4) 0.081(6) 0.082(7) 0.025(5) 0.005(4) 0.005(4) C4 0.052(5) 0.053(6) 0.104(10) 0.010(8) 0.005(6) 0.018(6) C5 0.060(4) 0.062(6) 0.091(7) 0.021(6) -0.006(4) 0.000(4) C6 0.110(5) 0.086(7) 0.087(7) 0.018(5) 0.021(4) 0.029(5) C7 0.084(4) 0.091(7) 0.091(7) 0.032(6) 0.022(5) 0.025(5) C8 0.092(5) 0.051(6) 0.103(9) 0.004(5) -0.006(6) 0.001(5) C9 0.079(7) 0.108(8) 0.097(8) -0.007(6) 0.013(5) 0.024(5) C10 0.108(6) 0.176(11) 0.062(7) 0.036(6) 0.030(5) -0.021(6) C11 0.117(7) 0.209(16) 0.159(13) 0.152(12) -0.029(6) -0.052(9) C12 0.182(15) 0.26(2) 0.21(2) 0.172(18) 0.124(14) 0.163(18) C13 0.143(14) 0.128(13) 0.30(3) 0.120(15) 0.137(16) 0.104(10) C14 0.178(12) 0.116(12) 0.30(3) 0.055(12) 0.018(15) -0.024(9) C15 0.178(12) 0.135(13) 0.260(19) 0.070(9) -0.036(11) -0.089(10) C16 0.060(7) 0.290(18) 0.204(14) -0.005(10) 0.010(7) 0.012(8) C17 0.128(9) 0.134(10) 0.122(9) -0.001(7) -0.005(7) 0.092(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 C18 1.679(10) . ? S2 C19 1.643(10) . ? N1 C18 1.407(14) . ? N1 H1N1 0.85(4) . ? N1 H2N1 0.85(4) . ? N2 C19 1.450(14) . ? N2 H1N2 0.98(4) . ? N2 H2N2 0.99(4) . ? C18 C19 1.440(9) . ? S1A C18A 1.52(2) . ? S2A C19A 1.80(2) . ? N1A C19A 1.17(5) . ? N1A H1N1 1.04(7) . ? N1A H2N1 1.31(7) . ? N2A C18A 1.59(4) . ? N2A H1N2 1.24(7) . ? N2A H2N2 0.65(7) . ? C18A C19A 1.71(2) . ? O1 C4 1.364(10) . ? O1 C8 1.439(8) . ? O2 C9 1.386(9) . ? O2 C10 1.451(9) . ? O3 C12 1.397(14) . ? O3 C11 1.473(13) . ? O4 C13 1.357(15) . ? O4 C14 1.446(15) . ? O5 C16 1.300(13) . ? O5 C15 1.437(12) . ? O6 C5 1.359(8) . ? O6 C17 1.411(11) . ? C1 C1 1.265(15) 2_675 ? C1 C2 1.471(11) . ? C1 H1 0.9300 . ? C2 C7 1.368(14) . ? C2 C3 1.394(10) . ? C3 C4 1.362(8) . ? C3 H3 0.9300 . ? C4 C5 1.437(13) . ? C5 C6 1.396(8) . ? C6 C7 1.400(8) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.510(10) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.358(18) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.523(18) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.169(15) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.513(12) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? O1A C4A 1.37(2) . ? O1A C8A 1.41(2) . ? O2A C9A 1.352(19) . ? O2A C10A 1.40(2) . ? O3A C12A 1.38(2) . ? O3A C11A 1.50(2) . ? O4A C13A 1.36(3) . ? O4A C14A 1.45(2) . ? O5A C16A 1.31(2) . ? O5A C15A 1.41(2) . ? O6A C5A 1.343(19) . ? O6A C17A 1.40(2) . ? C1A C2A 1.474(18) . ? C1A C1A 1.49(6) 2_675 ? C1A H1A 0.9300 . ? C2A C7A 1.37(2) . ? C2A C3A 1.398(19) . ? C3A C4A 1.371(18) . ? C3A H3A 0.9300 . ? C4A C5A 1.45(2) . ? C5A C6A 1.388(17) . ? C6A C7A 1.393(16) . ? C6A H6A 0.9300 . ? C7A H7A 0.9300 . ? C8A C9A 1.48(2) . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C9A H9A1 0.9700 . ? C9A H9A2 0.9700 . ? C10A C11A 1.32(2) . ? C10A H10C 0.9700 . ? C10A H10D 0.9700 . ? C11A H11C 0.9700 . ? C11A H11D 0.9700 . ? C12A C13A 1.56(3) . ? C12A H12C 0.9700 . ? C12A H12D 0.9700 . ? C13A H13C 0.9700 . ? C13A H13D 0.9700 . ? C14A C15A 1.19(2) . ? C14A H14C 0.9700 . ? C14A H14D 0.9700 . ? C15A H15C 0.9700 . ? C15A H15D 0.9700 . ? C16A C17A 1.55(2) . ? C16A H16C 0.9700 . ? C16A H16D 0.9700 . ? C17A H17C 0.9700 . ? C17A H17D 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 C18 N1 H1N1 137(4) . . ? C18 N1 H2N1 104(5) . . ? H1N1 N1 H2N1 119(6) . . ? C19 N2 H1N2 155(4) . . ? C19 N2 H2N2 97(4) . . ? H1N2 N2 H2N2 108(5) . . ? N1 C18 C19 109.8(10) . . ? N1 C18 S1 124.7(7) . . ? C19 C18 S1 124.9(9) . . ? C18 C19 N2 103.9(9) . . ? C18 C19 S2 122.6(9) . . ? N2 C19 S2 132.2(7) . . ? C19A N1A H1N1 99(5) . . ? C19A N1A H2N1 125(5) . . ? H1N1 N1A H2N1 76(5) . . ? C18A N2A H1N2 74(4) . . ? C18A N2A H2N2 153(10) . . ? H1N2 N2A H2N2 110(10) . . ? S1A C18A N2A 137(2) . . ? S1A C18A C19A 108.7(12) . . ? N2A C18A C19A 95(2) . . ? N1A C19A C18A 111(3) . . ? N1A C19A S2A 137(3) . . ? C18A C19A S2A 111.3(13) . . ? C4 O1 C8 117.0(8) . . ? C9 O2 C10 115.0(7) . . ? C12 O3 C11 113.4(9) . . ? C13 O4 C14 114.2(11) . . ? C16 O5 C15 106.2(10) . . ? C5 O6 C17 117.5(8) . . ? C1 C1 C2 128.7(17) 2_675 . ? C1 C1 H1 115.6 2_675 . ? C2 C1 H1 115.6 . . ? C7 C2 C3 118.2(9) . . ? C7 C2 C1 123.1(11) . . ? C3 C2 C1 118.7(14) . . ? C4 C3 C2 123.8(10) . . ? C4 C3 H3 118.1 . . ? C2 C3 H3 118.1 . . ? C3 C4 O1 128.5(12) . . ? C3 C4 C5 116.2(10) . . ? O1 C4 C5 115.1(8) . . ? O6 C5 C6 124.2(9) . . ? O6 C5 C4 114.4(8) . . ? C6 C5 C4 121.3(7) . . ? C5 C6 C7 118.2(7) . . ? C5 C6 H6 120.9 . . ? C7 C6 H6 120.9 . . ? C2 C7 C6 121.7(7) . . ? C2 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? O1 C8 C9 108.3(7) . . ? O1 C8 H8A 110.0 . . ? C9 C8 H8A 110.0 . . ? O1 C8 H8B 110.0 . . ? C9 C8 H8B 110.0 . . ? H8A C8 H8B 108.4 . . ? O2 C9 C8 109.1(6) . . ? O2 C9 H9A 109.9 . . ? C8 C9 H9A 109.9 . . ? O2 C9 H9B 109.9 . . ? C8 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? C11 C10 O2 114.6(10) . . ? C11 C10 H10A 108.6 . . ? O2 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? O2 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C10 C11 O3 109.0(9) . . ? C10 C11 H11A 109.9 . . ? O3 C11 H11A 109.9 . . ? C10 C11 H11B 109.9 . . ? O3 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? O3 C12 C13 105.7(12) . . ? O3 C12 H12A 110.6 . . ? C13 C12 H12A 110.6 . . ? O3 C12 H12B 110.6 . . ? C13 C12 H12B 110.6 . . ? H12A C12 H12B 108.7 . . ? O4 C13 C12 110.1(14) . . ? O4 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? O4 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.2 . . ? C15 C14 O4 121.9(17) . . ? C15 C14 H14A 106.9 . . ? O4 C14 H14A 106.9 . . ? C15 C14 H14B 106.9 . . ? O4 C14 H14B 106.9 . . ? H14A C14 H14B 106.7 . . ? C14 C15 O5 124.5(17) . . ? C14 C15 H15A 106.2 . . ? O5 C15 H15A 106.2 . . ? C14 C15 H15B 106.2 . . ? O5 C15 H15B 106.2 . . ? H15A C15 H15B 106.4 . . ? O5 C16 C17 106.2(9) . . ? O5 C16 H16A 110.5 . . ? C17 C16 H16A 110.5 . . ? O5 C16 H16B 110.5 . . ? C17 C16 H16B 110.5 . . ? H16A C16 H16B 108.7 . . ? O6 C17 C16 113.4(8) . . ? O6 C17 H17A 108.9 . . ? C16 C17 H17A 108.9 . . ? O6 C17 H17B 108.9 . . ? C16 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C4A O1A C8A 116(2) . . ? C9A O2A C10A 114.8(18) . . ? C12A O3A C11A 123(2) . . ? C13A O4A C14A 114(2) . . ? C16A O5A C15A 115(3) . . ? C5A O6A C17A 122(2) . . ? C2A C1A C1A 119(3) . 2_675 ? C2A C1A H1A 120.3 . . ? C1A C1A H1A 120.3 2_675 . ? C7A C2A C3A 115.7(18) . . ? C7A C2A C1A 124(2) . . ? C3A C2A C1A 119(2) . . ? C4A C3A C2A 122(2) . . ? C4A C3A H3A 119.1 . . ? C2A C3A H3A 119.1 . . ? O1A C4A C3A 125(2) . . ? O1A C4A C5A 112.7(18) . . ? C3A C4A C5A 117(2) . . ? O6A C5A C6A 125(2) . . ? O6A C5A C4A 114.8(19) . . ? C6A C5A C4A 120.5(16) . . ? C5A C6A C7A 116.1(17) . . ? C5A C6A H6A 121.9 . . ? C7A C6A H6A 121.9 . . ? C2A C7A C6A 125.6(17) . . ? C2A C7A H7A 117.2 . . ? C6A C7A H7A 117.2 . . ? O1A C8A C9A 114(2) . . ? O1A C8A H8A1 108.7 . . ? C9A C8A H8A1 108.7 . . ? O1A C8A H8A2 108.7 . . ? C9A C8A H8A2 108.7 . . ? H8A1 C8A H8A2 107.6 . . ? O2A C9A C8A 112(2) . . ? O2A C9A H9A1 109.2 . . ? C8A C9A H9A1 109.2 . . ? O2A C9A H9A2 109.2 . . ? C8A C9A H9A2 109.2 . . ? H9A1 C9A H9A2 107.9 . . ? C11A C10A O2A 145(2) . . ? C11A C10A H10C 100.6 . . ? O2A C10A H10C 100.6 . . ? C11A C10A H10D 100.6 . . ? O2A C10A H10D 100.6 . . ? H10C C10A H10D 104.3 . . ? C10A C11A O3A 107(2) . . ? C10A C11A H11C 110.4 . . ? O3A C11A H11C 110.4 . . ? C10A C11A H11D 110.4 . . ? O3A C11A H11D 110.4 . . ? H11C C11A H11D 108.6 . . ? O3A C12A C13A 104(2) . . ? O3A C12A H12C 110.9 . . ? C13A C12A H12C 110.9 . . ? O3A C12A H12D 110.9 . . ? C13A C12A H12D 110.9 . . ? H12C C12A H12D 108.9 . . ? O4A C13A C12A 104(2) . . ? O4A C13A H13C 111.1 . . ? C12A C13A H13C 111.1 . . ? O4A C13A H13D 111.1 . . ? C12A C13A H13D 111.1 . . ? H13C C13A H13D 109.0 . . ? C15A C14A O4A 115(4) . . ? C15A C14A H14C 108.5 . . ? O4A C14A H14C 108.5 . . ? C15A C14A H14D 108.5 . . ? O4A C14A H14D 108.5 . . ? H14C C14A H14D 107.5 . . ? C14A C15A O5A 122(4) . . ? C14A C15A H15C 106.8 . . ? O5A C15A H15C 106.8 . . ? C14A C15A H15D 106.8 . . ? O5A C15A H15D 106.8 . . ? H15C C15A H15D 106.6 . . ? O5A C16A C17A 100(2) . . ? O5A C16A H16C 111.9 . . ? C17A C16A H16C 111.9 . . ? O5A C16A H16D 111.9 . . ? C17A C16A H16D 111.9 . . ? H16C C16A H16D 109.6 . . ? O6A C17A C16A 116(2) . . ? O6A C17A H17C 108.2 . . ? C16A C17A H17C 108.2 . . ? O6A C17A H17D 108.2 . . ? C16A C17A H17D 108.2 . . ? H17C C17A H17D 107.4 . . ? 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 N1 C18 C19 N2 -166.9(10) . . . . ? S1 C18 C19 N2 4.5(10) . . . . ? N1 C18 C19 S2 24.3(11) . . . . ? S1 C18 C19 S2 -164.3(5) . . . . ? S1A C18A C19A N1A -18(3) . . . . ? N2A C18A C19A N1A -161(3) . . . . ? S1A C18A C19A S2A 170.7(11) . . . . ? N2A C18A C19A S2A 27(2) . . . . ? C1 C1 C2 C7 9(2) 2_675 . . . ? C1 C1 C2 C3 -171.1(11) 2_675 . . . ? C7 C2 C3 C4 -9.3(16) . . . . ? C1 C2 C3 C4 171.1(11) . . . . ? C2 C3 C4 O1 -177.8(12) . . . . ? C2 C3 C4 C5 6.8(18) . . . . ? C8 O1 C4 C3 -8.4(19) . . . . ? C8 O1 C4 C5 167.0(8) . . . . ? C17 O6 C5 C6 -21.4(9) . . . . ? C17 O6 C5 C4 156.4(9) . . . . ? C3 C4 C5 O6 -179.8(9) . . . . ? O1 C4 C5 O6 4.2(15) . . . . ? C3 C4 C5 C6 -1.9(16) . . . . ? O1 C4 C5 C6 -177.9(8) . . . . ? O6 C5 C6 C7 177.4(5) . . . . ? C4 C5 C6 C7 -0.4(11) . . . . ? C3 C2 C7 C6 6.6(14) . . . . ? C1 C2 C7 C6 -173.8(9) . . . . ? C5 C6 C7 C2 -2.1(10) . . . . ? C4 O1 C8 C9 169.1(9) . . . . ? C10 O2 C9 C8 177.2(6) . . . . ? O1 C8 C9 O2 64.1(8) . . . . ? C9 O2 C10 C11 176.2(9) . . . . ? O2 C10 C11 O3 -71.3(9) . . . . ? C12 O3 C11 C10 177.9(10) . . . . ? C11 O3 C12 C13 176.2(11) . . . . ? C14 O4 C13 C12 -173.1(12) . . . . ? O3 C12 C13 O4 70.3(13) . . . . ? C13 O4 C14 C15 143(2) . . . . ? O4 C14 C15 O5 20(4) . . . . ? C16 O5 C15 C14 -152(2) . . . . ? C15 O5 C16 C17 -177.6(10) . . . . ? C5 O6 C17 C16 -165.1(8) . . . . ? O5 C16 C17 O6 -61.6(13) . . . . ? C1A C1A C2A C7A -15(6) 2_675 . . . ? C1A C1A C2A C3A 151(4) 2_675 . . . ? C7A C2A C3A C4A -18(5) . . . . ? C1A C2A C3A C4A 174(4) . . . . ? C8A O1A C4A C3A 4(6) . . . . ? C8A O1A C4A C5A 158(3) . . . . ? C2A C3A C4A O1A 175(4) . . . . ? C2A C3A C4A C5A 22(6) . . . . ? C17A O6A C5A C6A -16(4) . . . . ? C17A O6A C5A C4A 163(4) . . . . ? O1A C4A C5A O6A 8(5) . . . . ? C3A C4A C5A O6A 165(3) . . . . ? O1A C4A C5A C6A -173(3) . . . . ? C3A C4A C5A C6A -16(6) . . . . ? O6A C5A C6A C7A -174(2) . . . . ? C4A C5A C6A C7A 7(4) . . . . ? C3A C2A C7A C6A 8(5) . . . . ? C1A C2A C7A C6A 175(3) . . . . ? C5A C6A C7A C2A -3(4) . . . . ? C4A O1A C8A C9A 133(3) . . . . ? C10A O2A C9A C8A -139(2) . . . . ? O1A C8A C9A O2A 80(4) . . . . ? C9A O2A C10A C11A -176(4) . . . . ? O2A C10A C11A O3A -107(4) . . . . ? C12A O3A C11A C10A 132(3) . . . . ? C11A O3A C12A C13A -176(2) . . . . ? C14A O4A C13A C12A -177(3) . . . . ? O3A C12A C13A O4A 85(3) . . . . ? C13A O4A C14A C15A -179(4) . . . . ? O4A C14A C15A O5A -72(7) . . . . ? C16A O5A C15A C14A 171(5) . . . . ? C15A O5A C16A C17A 174(4) . . . . ? C5A O6A C17A C16A 173(3) . . . . ? O5A C16A C17A O6A 67(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 N1 H1N1 O6 0.85(4) 2.49(5) 3.275(11) 153(6) . N1 H2N1 O4 0.85(4) 2.33(4) 3.166(12) 170(6) . N2 H1N2 O3 0.98(4) 2.35(5) 3.253(14) 152(6) 1_655 N2 H2N2 O1 0.99(4) 2.38(5) 3.346(11) 166(6) 1_655 _diffrn_measured_fraction_theta_max 0.852 _diffrn_reflns_theta_full 24.68 _diffrn_measured_fraction_theta_full 0.852 _refine_diff_density_max 0.099 _refine_diff_density_min -0.126 _refine_diff_density_rms 0.027 # Attachment 'Bas2.cif' data_bas2 #TrackingRef 'C004680A_ccdc_771037_771042_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 771038' #TrackingRef 'Bas2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3,5,6,8,9,11,12-octahydro-thieno[3,4-b]- 1,4,7,10,13-pentaoxacyclopentadecyne ; _chemical_name_common ;2,3,5,6,8,9,11,12-octahydro-thieno(3,4-b)-1,4,7,10,13- pentaoxacyclopentadecyne ; _chemical_melting_point ? _chemical_formula_moiety 'C12 H18 O5 S' _chemical_formula_sum 'C12 H18 O5 S' _chemical_formula_weight 274.32 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' 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 Orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 16.674(3) _cell_length_b 8.545(2) _cell_length_c 19.279(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2746.9(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14103 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 25.37 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.246 _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 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 'Nonius KappaCCD' _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 2400 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.37 _reflns_number_total 2400 _reflns_number_gt 1315 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics MERCURY _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^)+(0.0860P)^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 SHELXL _refine_ls_extinction_coef 0.0122(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2400 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1118 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1580 _refine_ls_wR_factor_gt 0.1407 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.36925(8) 0.01493(14) 0.02815(5) 0.1186(5) Uani 1 1 d . . . O1 O 0.43762(12) 0.14881(19) 0.21000(9) 0.0627(6) Uani 1 1 d . . . O2 O 0.54923(12) 0.0776(2) 0.31528(9) 0.0681(6) Uani 1 1 d . . . O3 O 0.42546(14) -0.0297(2) 0.41018(10) 0.0780(7) Uani 1 1 d . . . O4 O 0.28749(13) -0.1905(2) 0.33452(10) 0.0724(6) Uani 1 1 d . . . O5 O 0.29628(11) 0.00911(17) 0.21913(10) 0.0609(6) Uani 1 1 d . . . C1 C 0.40446(19) 0.0971(3) 0.15027(14) 0.0578(8) Uani 1 1 d . . . C2 C 0.52017(17) 0.1932(3) 0.20721(15) 0.0674(8) Uani 1 1 d . . . H2A H 0.5265 0.2871 0.1795 0.081 Uiso 1 1 calc R . . H2B H 0.5519 0.1103 0.1865 0.081 Uiso 1 1 calc R . . C3 C 0.54669(19) 0.2222(3) 0.27902(15) 0.0726(9) Uani 1 1 d . . . H3A H 0.5995 0.2699 0.2789 0.087 Uiso 1 1 calc R . . H3B H 0.5098 0.2932 0.3018 0.087 Uiso 1 1 calc R . . C4 C 0.5500(2) 0.0918(4) 0.38834(16) 0.0806(9) Uani 1 1 d . . . H4A H 0.5827 0.1811 0.4012 0.097 Uiso 1 1 calc R . . H4B H 0.5744 -0.0010 0.4082 0.097 Uiso 1 1 calc R . . C5 C 0.4677(2) 0.1118(4) 0.41823(16) 0.0836(10) Uani 1 1 d . . . H5A H 0.4715 0.1386 0.4670 0.100 Uiso 1 1 calc R . . H5B H 0.4398 0.1956 0.3944 0.100 Uiso 1 1 calc R . . C6 C 0.3427(2) -0.0147(4) 0.42195(19) 0.0960(11) Uani 1 1 d . . . H6A H 0.3215 0.0693 0.3935 0.115 Uiso 1 1 calc R . . H6B H 0.3333 0.0119 0.4702 0.115 Uiso 1 1 calc R . . C7 C 0.3008(2) -0.1611(4) 0.40527(18) 0.0903(11) Uani 1 1 d . . . H7A H 0.3316 -0.2474 0.4242 0.108 Uiso 1 1 calc R . . H7B H 0.2493 -0.1603 0.4287 0.108 Uiso 1 1 calc R . . C8 C 0.2200(2) -0.1169(3) 0.30428(17) 0.0794(9) Uani 1 1 d . . . H8A H 0.2124 -0.0142 0.3247 0.095 Uiso 1 1 calc R . . H8B H 0.1722 -0.1786 0.3131 0.095 Uiso 1 1 calc R . . C9 C 0.23277(18) -0.1017(3) 0.22828(17) 0.0715(9) Uani 1 1 d . . . H9A H 0.2475 -0.2020 0.2084 0.086 Uiso 1 1 calc R . . H9B H 0.1842 -0.0651 0.2058 0.086 Uiso 1 1 calc R . . C10 C 0.32921(19) 0.0216(3) 0.15514(16) 0.0586(8) Uani 1 1 d . . . C11 C 0.3027(2) -0.0291(4) 0.09251(18) 0.0893(11) Uani 1 1 d . . . H11 H 0.2544 -0.0811 0.0855 0.107 Uiso 1 1 calc R . . C12 C 0.4326(2) 0.1023(4) 0.08501(15) 0.0824(10) Uani 1 1 d . . . H12 H 0.4810 0.1484 0.0725 0.099 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 0.1391(13) 0.1557(10) 0.0610(6) 0.0075(5) -0.0241(6) 0.0012(8) O1 0.0523(13) 0.0688(11) 0.0669(12) 0.0010(9) 0.0062(10) -0.0131(9) O2 0.0640(15) 0.0684(12) 0.0720(14) 0.0019(9) -0.0038(10) -0.0051(10) O3 0.0679(17) 0.0777(13) 0.0883(15) -0.0081(10) 0.0164(12) -0.0017(12) O4 0.0700(16) 0.0655(11) 0.0818(14) 0.0037(9) -0.0018(11) 0.0025(10) O5 0.0515(13) 0.0441(9) 0.0870(14) -0.0025(8) 0.0026(10) -0.0068(8) C1 0.059(2) 0.0545(15) 0.0593(19) 0.0097(12) -0.0041(15) 0.0055(14) C2 0.057(2) 0.0666(17) 0.079(2) 0.0157(13) 0.0072(16) -0.0166(15) C3 0.063(2) 0.0634(17) 0.091(2) -0.0006(15) -0.0005(17) -0.0250(15) C4 0.075(3) 0.095(2) 0.072(2) -0.0042(16) -0.0173(18) -0.0149(18) C5 0.091(3) 0.085(2) 0.074(2) -0.0218(16) -0.0008(19) 0.0026(19) C6 0.083(3) 0.109(3) 0.096(3) -0.0205(18) 0.015(2) 0.008(2) C7 0.084(3) 0.085(2) 0.103(3) 0.0087(18) 0.025(2) -0.0016(19) C8 0.049(2) 0.0649(17) 0.125(3) 0.0121(17) 0.0135(19) -0.0057(15) C9 0.0469(19) 0.0543(15) 0.113(3) 0.0110(14) -0.0145(17) -0.0070(14) C10 0.061(2) 0.0459(13) 0.0686(19) 0.0053(12) -0.0130(16) 0.0095(14) C11 0.081(3) 0.088(2) 0.099(3) 0.0037(18) -0.036(2) 0.0051(19) C12 0.085(3) 0.100(2) 0.062(2) 0.0167(16) -0.0006(18) 0.0005(19) _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 C12 1.695(4) . ? S1 C11 1.707(4) . ? O1 C1 1.352(3) . ? O1 C2 1.429(3) . ? O2 C4 1.414(3) . ? O2 C3 1.420(3) . ? O3 C6 1.405(4) . ? O3 C5 1.408(4) . ? O4 C7 1.405(4) . ? O4 C8 1.415(4) . ? O5 C10 1.355(3) . ? O5 C9 1.432(3) . ? C1 C12 1.343(4) . ? C1 C10 1.414(4) . ? C2 C3 1.474(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.497(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.468(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.486(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.357(4) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? 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 C12 S1 C11 91.83(17) . . ? C1 O1 C2 116.7(2) . . ? C4 O2 C3 114.6(2) . . ? C6 O3 C5 113.3(2) . . ? C7 O4 C8 116.5(2) . . ? C10 O5 C9 117.6(2) . . ? C12 C1 O1 130.1(3) . . ? C12 C1 C10 112.7(3) . . ? O1 C1 C10 117.1(2) . . ? O1 C2 C3 107.4(2) . . ? O1 C2 H2A 110.2 . . ? C3 C2 H2A 110.2 . . ? O1 C2 H2B 110.2 . . ? C3 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? O2 C3 C2 109.0(2) . . ? O2 C3 H3A 109.9 . . ? C2 C3 H3A 109.9 . . ? O2 C3 H3B 109.9 . . ? C2 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? O2 C4 C5 112.7(3) . . ? O2 C4 H4A 109.1 . . ? C5 C4 H4A 109.1 . . ? O2 C4 H4B 109.1 . . ? C5 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? O3 C5 C4 108.5(2) . . ? O3 C5 H5A 110.0 . . ? C4 C5 H5A 110.0 . . ? O3 C5 H5B 110.0 . . ? C4 C5 H5B 110.0 . . ? H5A C5 H5B 108.4 . . ? O3 C6 C7 110.8(3) . . ? O3 C6 H6A 109.5 . . ? C7 C6 H6A 109.5 . . ? O3 C6 H6B 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? O4 C7 C6 116.1(3) . . ? O4 C7 H7A 108.3 . . ? C6 C7 H7A 108.3 . . ? O4 C7 H7B 108.3 . . ? C6 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? O4 C8 C9 109.3(3) . . ? O4 C8 H8A 109.8 . . ? C9 C8 H8A 109.8 . . ? O4 C8 H8B 109.8 . . ? C9 C8 H8B 109.8 . . ? H8A C8 H8B 108.3 . . ? O5 C9 C8 106.6(2) . . ? O5 C9 H9A 110.4 . . ? C8 C9 H9A 110.4 . . ? O5 C9 H9B 110.4 . . ? C8 C9 H9B 110.4 . . ? H9A C9 H9B 108.6 . . ? O5 C10 C11 130.8(3) . . ? O5 C10 C1 117.1(2) . . ? C11 C10 C1 112.1(3) . . ? C10 C11 S1 111.4(3) . . ? C10 C11 H11 124.3 . . ? S1 C11 H11 124.3 . . ? C1 C12 S1 112.0(3) . . ? C1 C12 H12 124.0 . . ? S1 C12 H12 124.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 O1 C1 C12 -11.6(4) . . . . ? C2 O1 C1 C10 166.7(2) . . . . ? C1 O1 C2 C3 -171.6(2) . . . . ? C4 O2 C3 C2 -161.9(2) . . . . ? O1 C2 C3 O2 69.4(3) . . . . ? C3 O2 C4 C5 83.3(3) . . . . ? C6 O3 C5 C4 -166.5(3) . . . . ? O2 C4 C5 O3 69.2(3) . . . . ? C5 O3 C6 C7 173.7(3) . . . . ? C8 O4 C7 C6 -82.4(4) . . . . ? O3 C6 C7 O4 -78.0(4) . . . . ? C7 O4 C8 C9 156.0(2) . . . . ? C10 O5 C9 C8 168.0(2) . . . . ? O4 C8 C9 O5 -68.0(3) . . . . ? C9 O5 C10 C11 15.7(4) . . . . ? C9 O5 C10 C1 -163.2(2) . . . . ? C12 C1 C10 O5 179.3(2) . . . . ? O1 C1 C10 O5 0.8(3) . . . . ? C12 C1 C10 C11 0.2(3) . . . . ? O1 C1 C10 C11 -178.3(2) . . . . ? O5 C10 C11 S1 -178.9(2) . . . . ? C1 C10 C11 S1 0.1(3) . . . . ? C12 S1 C11 C10 -0.3(2) . . . . ? O1 C1 C12 S1 177.8(2) . . . . ? C10 C1 C12 S1 -0.5(3) . . . . ? C11 S1 C12 C1 0.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.350 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.042 # Attachment 'bas3.cif' data_bas3 #TrackingRef 'C004680A_ccdc_771037_771042_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 771039' #TrackingRef 'bas3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3,5,6,8,9,11,12-octahydronaphtho[2,3-b][1,4,7,10,13] pentaoxacyclopentadecine 3-nitro-1H-1,2,4-triazole clathrate ; _chemical_name_common ; 2,3,5,6,8,9,11,12-octahydronaphtho(2,3-b)(1,4,7,10,13) pentaoxacyclopentadecine 3-nitro-1H-1,2,4-triazole clathrate ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 O5, C2 H2 N4 O2' _chemical_formula_sum 'C20 H24 N4 O7' _chemical_formula_weight 432.43 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' _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 7.219(1) _cell_length_b 10.992(2) _cell_length_c 13.356(3) _cell_angle_alpha 89.43(2) _cell_angle_beta 78.84(2) _cell_angle_gamma 80.80(2) _cell_volume 1026.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8141 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 25.14 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.107 _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 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 'Nonius KappaCCD' _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 3520 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0752 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.14 _reflns_number_total 3520 _reflns_number_gt 1927 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics MERCURY _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^)+(0.0672P)^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 SHELXL _refine_ls_extinction_coef 0.056(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3520 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1294 _refine_ls_wR_factor_gt 0.1088 _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_restrained_S_all 0.930 _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 -0.0079(2) 0.16015(15) 0.81828(13) 0.0553(5) Uani 1 1 d . . . O2 O 0.1063(3) 0.30413(17) 0.96929(15) 0.0664(5) Uani 1 1 d . . . O3 O 0.5012(3) 0.33928(17) 0.84956(15) 0.0679(6) Uani 1 1 d . . . O4 O 0.4834(2) 0.29679(15) 0.64394(14) 0.0576(5) Uani 1 1 d . . . O5 O 0.1654(2) 0.18178(15) 0.63666(13) 0.0555(5) Uani 1 1 d . . . O6 O 0.5239(3) -0.26323(19) 0.68379(19) 0.0854(7) Uani 1 1 d . . . O7 O 0.4879(3) -0.2951(2) 0.84481(19) 0.0919(7) Uani 1 1 d . . . N1 N 0.5008(3) -0.2282(2) 0.7713(2) 0.0595(6) Uani 1 1 d . . . N2 N 0.4500(3) -0.0536(2) 0.88902(18) 0.0588(6) Uani 1 1 d . . . N3 N 0.5139(3) -0.0211(2) 0.71863(17) 0.0556(6) Uani 1 1 d . . . N4 N 0.4868(3) 0.0845(2) 0.77299(19) 0.0581(6) Uani 1 1 d . . . H4 H 0.4925 0.1558 0.7466 0.070 Uiso 1 1 calc R . . C1 C 0.0208(3) 0.0557(2) 0.7589(2) 0.0478(6) Uani 1 1 d . . . C2 C -0.0725(4) 0.1517(3) 0.9254(2) 0.0586(7) Uani 1 1 d . . . H2A H 0.0134 0.0890 0.9528 0.070 Uiso 1 1 calc R . . H2B H -0.1992 0.1288 0.9390 0.070 Uiso 1 1 calc R . . C3 C -0.0779(4) 0.2731(3) 0.9745(2) 0.0650(8) Uani 1 1 d . . . H3A H -0.1535 0.3363 0.9415 0.078 Uiso 1 1 calc R . . H3B H -0.1405 0.2715 1.0456 0.078 Uiso 1 1 calc R . . C4 C 0.1547(4) 0.3913(3) 0.8932(2) 0.0794(9) Uani 1 1 d . . . H4A H 0.0572 0.4641 0.9028 0.095 Uiso 1 1 calc R . . H4B H 0.1614 0.3559 0.8260 0.095 Uiso 1 1 calc R . . C5 C 0.3426(4) 0.4254(3) 0.9005(3) 0.0864(11) Uani 1 1 d . . . H5A H 0.3507 0.5060 0.8713 0.104 Uiso 1 1 calc R . . H5B H 0.3504 0.4314 0.9719 0.104 Uiso 1 1 calc R . . C6 C 0.6174(4) 0.3885(3) 0.7666(2) 0.0615(7) Uani 1 1 d . . . H6A H 0.7370 0.3321 0.7475 0.074 Uiso 1 1 calc R . . H6B H 0.6471 0.4658 0.7884 0.074 Uiso 1 1 calc R . . C7 C 0.5274(4) 0.4105(2) 0.6750(2) 0.0644(8) Uani 1 1 d . . . H7A H 0.4116 0.4707 0.6915 0.077 Uiso 1 1 calc R . . H7B H 0.6147 0.4421 0.6201 0.077 Uiso 1 1 calc R . . C8 C 0.3823(4) 0.3085(2) 0.5618(2) 0.0568(7) Uani 1 1 d . . . H8A H 0.4664 0.3268 0.4995 0.068 Uiso 1 1 calc R . . H8B H 0.2753 0.3756 0.5765 0.068 Uiso 1 1 calc R . . C9 C 0.3116(3) 0.1908(2) 0.54845(19) 0.0542(7) Uani 1 1 d . . . H9A H 0.2595 0.1918 0.4867 0.065 Uiso 1 1 calc R . . H9B H 0.4146 0.1215 0.5441 0.065 Uiso 1 1 calc R . . C10 C 0.1119(3) 0.0692(2) 0.6564(2) 0.0478(6) Uani 1 1 d . . . C11 C 0.1437(3) -0.0264(2) 0.5885(2) 0.0525(7) Uani 1 1 d . . . H11 H 0.2003 -0.0161 0.5209 0.063 Uiso 1 1 calc R . . C12 C 0.0916(3) -0.1420(2) 0.6195(2) 0.0506(7) Uani 1 1 d . . . C13 C 0.1202(3) -0.2416(3) 0.5506(2) 0.0615(8) Uani 1 1 d . . . H13 H 0.1720 -0.2318 0.4822 0.074 Uiso 1 1 calc R . . C14 C 0.0731(4) -0.3528(3) 0.5825(3) 0.0681(8) Uani 1 1 d . . . H14 H 0.0920 -0.4180 0.5359 0.082 Uiso 1 1 calc R . . C15 C -0.0032(4) -0.3688(3) 0.6848(3) 0.0703(9) Uani 1 1 d . . . H15 H -0.0323 -0.4455 0.7064 0.084 Uiso 1 1 calc R . . C16 C -0.0356(3) -0.2742(3) 0.7532(2) 0.0628(8) Uani 1 1 d . . . H16 H -0.0876 -0.2862 0.8212 0.075 Uiso 1 1 calc R . . C17 C 0.0090(3) -0.1567(2) 0.7221(2) 0.0500(7) Uani 1 1 d . . . C18 C -0.0283(3) -0.0551(2) 0.7912(2) 0.0521(7) Uani 1 1 d . . . H18 H -0.0866 -0.0637 0.8587 0.063 Uiso 1 1 calc R . . C19 C 0.4890(3) -0.0983(2) 0.7936(2) 0.0475(6) Uani 1 1 d . . . C20 C 0.4501(4) 0.0650(3) 0.8722(2) 0.0609(7) Uani 1 1 d . . . H20 H 0.4276 0.1260 0.9228 0.073 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 0.0636(11) 0.0543(12) 0.0440(12) 0.0034(9) -0.0014(8) -0.0091(8) O2 0.0745(13) 0.0662(13) 0.0606(13) 0.0104(10) -0.0081(10) -0.0245(10) O3 0.0829(13) 0.0528(12) 0.0656(14) 0.0009(10) -0.0031(11) -0.0180(10) O4 0.0719(12) 0.0454(11) 0.0572(13) 0.0098(9) -0.0147(9) -0.0121(8) O5 0.0629(11) 0.0496(11) 0.0493(12) 0.0068(9) 0.0011(9) -0.0106(8) O6 0.1097(17) 0.0711(15) 0.0754(17) -0.0199(13) -0.0188(13) -0.0125(12) O7 0.1239(18) 0.0524(13) 0.0889(18) 0.0158(13) 0.0098(14) -0.0207(12) N1 0.0551(13) 0.0513(16) 0.0668(18) 0.0018(15) 0.0005(12) -0.0081(11) N2 0.0691(14) 0.0518(15) 0.0544(16) 0.0051(12) -0.0068(11) -0.0128(11) N3 0.0622(14) 0.0505(14) 0.0572(16) 0.0062(13) -0.0182(11) -0.0104(10) N4 0.0653(14) 0.0443(14) 0.0672(18) 0.0153(13) -0.0191(12) -0.0102(10) C1 0.0428(14) 0.0476(16) 0.0517(18) 0.0015(14) -0.0086(12) -0.0040(11) C2 0.0579(16) 0.069(2) 0.0464(19) 0.0039(14) 0.0007(13) -0.0153(13) C3 0.0634(18) 0.067(2) 0.060(2) -0.0051(16) -0.0033(14) -0.0083(14) C4 0.092(2) 0.062(2) 0.074(2) 0.0050(18) 0.0019(18) -0.0085(17) C5 0.103(2) 0.064(2) 0.084(3) -0.0197(18) 0.0188(19) -0.0349(18) C6 0.0613(16) 0.0577(18) 0.064(2) -0.0009(15) -0.0012(14) -0.0182(13) C7 0.0753(19) 0.0413(16) 0.076(2) 0.0073(15) -0.0099(16) -0.0138(13) C8 0.0645(17) 0.0580(18) 0.0468(18) 0.0165(14) -0.0087(13) -0.0097(13) C9 0.0565(15) 0.0646(19) 0.0389(16) 0.0084(13) -0.0024(12) -0.0113(13) C10 0.0399(13) 0.0518(17) 0.0487(17) 0.0076(14) -0.0046(11) -0.0044(11) C11 0.0491(15) 0.0597(18) 0.0459(17) 0.0021(14) -0.0071(12) -0.0031(12) C12 0.0405(14) 0.0516(18) 0.0601(19) -0.0003(14) -0.0138(12) -0.0041(11) C13 0.0564(16) 0.0608(19) 0.068(2) -0.0036(16) -0.0175(14) -0.0048(13) C14 0.0625(18) 0.054(2) 0.088(3) -0.0098(18) -0.0164(17) -0.0066(14) C15 0.0634(19) 0.054(2) 0.098(3) 0.0052(19) -0.0195(17) -0.0164(14) C16 0.0549(16) 0.061(2) 0.075(2) 0.0121(17) -0.0144(14) -0.0186(13) C17 0.0366(13) 0.0554(18) 0.0576(19) 0.0040(14) -0.0093(12) -0.0065(11) C18 0.0422(14) 0.0639(19) 0.0477(17) 0.0057(15) -0.0025(11) -0.0092(12) C19 0.0468(14) 0.0400(15) 0.0569(19) 0.0074(14) -0.0126(12) -0.0082(11) C20 0.0677(17) 0.0514(19) 0.064(2) -0.0019(15) -0.0135(15) -0.0099(13) _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 C1 1.366(3) . ? O1 C2 1.423(3) . ? O2 C3 1.414(3) . ? O2 C4 1.423(3) . ? O3 C6 1.414(3) . ? O3 C5 1.427(3) . ? O4 C7 1.422(3) . ? O4 C8 1.425(3) . ? O5 C10 1.362(3) . ? O5 C9 1.436(3) . ? O6 N1 1.206(3) . ? O7 N1 1.220(3) . ? N1 C19 1.447(3) . ? N2 C20 1.321(3) . ? N2 C19 1.332(3) . ? N3 C19 1.310(3) . ? N3 N4 1.342(3) . ? N4 C20 1.322(3) . ? N4 H4 0.8600 . ? C1 C18 1.365(3) . ? C1 C10 1.418(3) . ? C2 C3 1.484(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.485(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.493(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.489(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.357(3) . ? C11 C12 1.417(4) . ? C11 H11 0.9300 . ? C12 C13 1.401(4) . ? C12 C17 1.404(3) . ? C13 C14 1.362(4) . ? C13 H13 0.9300 . ? C14 C15 1.391(4) . ? C14 H14 0.9300 . ? C15 C16 1.353(4) . ? C15 H15 0.9300 . ? C16 C17 1.419(3) . ? C16 H16 0.9300 . ? C17 C18 1.414(3) . ? C18 H18 0.9300 . ? C20 H20 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C2 118.5(2) . . ? C3 O2 C4 113.9(2) . . ? C6 O3 C5 114.2(2) . . ? C7 O4 C8 113.36(19) . . ? C10 O5 C9 117.34(19) . . ? O6 N1 O7 124.6(3) . . ? O6 N1 C19 119.5(3) . . ? O7 N1 C19 115.9(3) . . ? C20 N2 C19 100.6(2) . . ? C19 N3 N4 99.4(2) . . ? C20 N4 N3 111.5(2) . . ? C20 N4 H4 124.3 . . ? N3 N4 H4 124.3 . . ? C18 C1 O1 125.6(2) . . ? C18 C1 C10 120.2(2) . . ? O1 C1 C10 114.2(2) . . ? O1 C2 C3 108.9(2) . . ? O1 C2 H2A 109.9 . . ? C3 C2 H2A 109.9 . . ? O1 C2 H2B 109.9 . . ? C3 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? O2 C3 C2 112.7(2) . . ? O2 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? O2 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? O2 C4 C5 109.3(3) . . ? O2 C4 H4A 109.8 . . ? C5 C4 H4A 109.8 . . ? O2 C4 H4B 109.8 . . ? C5 C4 H4B 109.8 . . ? H4A C4 H4B 108.3 . . ? O3 C5 C4 113.2(2) . . ? O3 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? O3 C5 H5B 108.9 . . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.8 . . ? O3 C6 C7 113.7(2) . . ? O3 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? O3 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? O4 C7 C6 108.4(2) . . ? O4 C7 H7A 110.0 . . ? C6 C7 H7A 110.0 . . ? O4 C7 H7B 110.0 . . ? C6 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? O4 C8 C9 109.0(2) . . ? O4 C8 H8A 109.9 . . ? C9 C8 H8A 109.9 . . ? O4 C8 H8B 109.9 . . ? C9 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? O5 C9 C8 106.0(2) . . ? O5 C9 H9A 110.5 . . ? C8 C9 H9A 110.5 . . ? O5 C9 H9B 110.5 . . ? C8 C9 H9B 110.5 . . ? H9A C9 H9B 108.7 . . ? C11 C10 O5 125.8(2) . . ? C11 C10 C1 120.3(2) . . ? O5 C10 C1 113.9(2) . . ? C10 C11 C12 120.7(3) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C17 119.3(3) . . ? C13 C12 C11 121.8(3) . . ? C17 C12 C11 118.9(2) . . ? C14 C13 C12 120.8(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 120.1(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 120.7(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 120.6(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C12 C17 C18 119.6(2) . . ? C12 C17 C16 118.4(3) . . ? C18 C17 C16 122.0(3) . . ? C1 C18 C17 120.2(2) . . ? C1 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? N3 C19 N2 118.4(2) . . ? N3 C19 N1 119.8(3) . . ? N2 C19 N1 121.8(3) . . ? N2 C20 N4 110.2(3) . . ? N2 C20 H20 124.9 . . ? N4 C20 H20 124.9 . . ? 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 C19 N3 N4 C20 0.3(2) . . . . ? C2 O1 C1 C18 8.2(3) . . . . ? C2 O1 C1 C10 -171.01(19) . . . . ? C1 O1 C2 C3 175.39(18) . . . . ? C4 O2 C3 C2 102.3(3) . . . . ? O1 C2 C3 O2 -67.6(3) . . . . ? C3 O2 C4 C5 175.0(2) . . . . ? C6 O3 C5 C4 116.4(3) . . . . ? O2 C4 C5 O3 82.7(3) . . . . ? C5 O3 C6 C7 -72.8(3) . . . . ? C8 O4 C7 C6 175.2(2) . . . . ? O3 C6 C7 O4 -58.2(3) . . . . ? C7 O4 C8 C9 -169.4(2) . . . . ? C10 O5 C9 C8 -163.54(19) . . . . ? O4 C8 C9 O5 68.9(3) . . . . ? C9 O5 C10 C11 -18.7(3) . . . . ? C9 O5 C10 C1 159.3(2) . . . . ? C18 C1 C10 C11 2.7(3) . . . . ? O1 C1 C10 C11 -178.00(19) . . . . ? C18 C1 C10 O5 -175.4(2) . . . . ? O1 C1 C10 O5 3.9(3) . . . . ? O5 C10 C11 C12 176.1(2) . . . . ? C1 C10 C11 C12 -1.8(3) . . . . ? C10 C11 C12 C13 179.0(2) . . . . ? C10 C11 C12 C17 -1.0(3) . . . . ? C17 C12 C13 C14 -1.5(3) . . . . ? C11 C12 C13 C14 178.5(2) . . . . ? C12 C13 C14 C15 -0.5(4) . . . . ? C13 C14 C15 C16 1.5(4) . . . . ? C14 C15 C16 C17 -0.5(4) . . . . ? C13 C12 C17 C18 -177.1(2) . . . . ? C11 C12 C17 C18 2.9(3) . . . . ? C13 C12 C17 C16 2.4(3) . . . . ? C11 C12 C17 C16 -177.5(2) . . . . ? C15 C16 C17 C12 -1.5(4) . . . . ? C15 C16 C17 C18 178.1(2) . . . . ? O1 C1 C18 C17 180.00(19) . . . . ? C10 C1 C18 C17 -0.8(3) . . . . ? C12 C17 C18 C1 -2.0(3) . . . . ? C16 C17 C18 C1 178.4(2) . . . . ? N4 N3 C19 N2 -0.3(3) . . . . ? N4 N3 C19 N1 178.63(19) . . . . ? C20 N2 C19 N3 0.1(3) . . . . ? C20 N2 C19 N1 -178.7(2) . . . . ? O6 N1 C19 N3 -3.7(3) . . . . ? O7 N1 C19 N3 175.6(2) . . . . ? O6 N1 C19 N2 175.1(2) . . . . ? O7 N1 C19 N2 -5.6(3) . . . . ? C19 N2 C20 N4 0.1(3) . . . . ? N3 N4 C20 N2 -0.3(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 N4 H4 O4 0.86 2.06 2.887(3) 160.9 . N4 H4 O3 0.86 2.47 3.015(3) 122.2 . C8 H8A O6 0.97 2.54 3.245(4) 129.8 2_656 C5 H5A O7 0.97 2.53 3.431(4) 153.6 1_565 _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.187 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.047 # Attachment 'bas4r.cif' data_bas4r _database_code_depnum_ccdc_archive 'CCDC 771040' #TrackingRef 'bas4r.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3,5,6,8,9,11,12-octahydro-thieno[3,4-b]- 1,4,7,10,13-pentaoxacyclopentadecyne ethanebis(thioamide) ; _chemical_name_common ; 2,3,5,6,8,9,11,12-octahydro-thieno(3,4-b)-1,4,7,10,13- pentaoxacyclopentadecyne ethanebis(thioamide) ; _chemical_melting_point ? _chemical_formula_moiety 'C12 H18 O5 S, C2 H4 N2 S2' _chemical_formula_sum 'C14 H22 N2 O5 S3' _chemical_formula_weight 394.52 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' O O 0.0106 0.0060 '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/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.945(2) _cell_length_b 15.102(3) _cell_length_c 12.647(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.68(2) _cell_angle_gamma 90.00 _cell_volume 1898.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14460 _cell_measurement_theta_min 1.61 _cell_measurement_theta_max 26.72 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.416 _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 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 'Nonius KappaCCD' _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 13416 _diffrn_reflns_av_R_equivalents 0.0592 _diffrn_reflns_av_sigmaI/netI 0.0550 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3524 _reflns_number_gt 2206 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2001)' _computing_cell_refinement 'DENZO SMN (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO SMN (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Mercury _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^)+(0.0408P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0147(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3524 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0902 _refine_ls_wR_factor_gt 0.0829 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 1.23358(6) 0.08595(5) 0.60436(5) 0.0739(2) Uani 1 1 d . . . S2 S 0.9288(5) 0.1681(2) 0.8756(3) 0.0524(5) Uani 0.746(6) 1 d P A 1 S3 S 1.1633(3) 0.38576(18) 0.73962(19) 0.0642(5) Uani 0.746(6) 1 d P A 1 N1 N 1.1704(13) 0.2720(8) 0.9128(5) 0.0547(12) Uani 0.746(6) 1 d P A 1 H1N1 H 1.234(3) 0.294(3) 0.921(3) 0.082 Uiso 0.746(6) 1 d P A 1 H2N1 H 1.150(4) 0.235(3) 0.949(3) 0.082 Uiso 0.746(6) 1 d P A 1 N2 N 0.9071(7) 0.2831(4) 0.7131(5) 0.0476(12) Uani 0.746(6) 1 d P A 1 H1N2 H 0.840(3) 0.253(2) 0.699(2) 0.071 Uiso 0.746(6) 1 d P A 1 H2N2 H 0.930(4) 0.323(3) 0.673(3) 0.071 Uiso 0.746(6) 1 d P A 1 C13 C 1.1068(3) 0.3043(2) 0.8202(3) 0.0502(11) Uani 0.746(6) 1 d P A 1 C14 C 0.9764(3) 0.2560(2) 0.7976(3) 0.0464(11) Uani 0.746(6) 1 d P A 1 S3A S 1.1276(7) 0.3925(6) 0.7602(6) 0.0642(5) Uani 0.254(6) 1 d P A 2 S2A S 0.9244(15) 0.1888(6) 0.8765(11) 0.0524(5) Uani 0.254(6) 1 d P A 2 N1A N 1.170(4) 0.263(3) 0.890(2) 0.0547(12) Uani 0.254(6) 1 d P A 2 N2A N 0.928(3) 0.3073(16) 0.7026(19) 0.0476(12) Uani 0.254(6) 1 d P A 2 C13A C 1.0345(8) 0.3123(5) 0.7603(6) 0.027(2) Uani 0.254(6) 1 d P A 2 C14A C 1.0463(8) 0.2467(5) 0.8585(6) 0.027(3) Uani 0.254(6) 1 d P A 2 O1 O 0.84843(14) 0.11304(10) 0.55708(10) 0.0526(4) Uani 1 1 d . . . O2 O 0.64182(14) 0.17865(11) 0.67625(11) 0.0595(4) Uani 1 1 d . . . O3 O 0.64081(14) 0.34863(10) 0.59857(10) 0.0538(4) Uani 1 1 d . . . O4 O 0.87292(14) 0.40929(10) 0.51329(10) 0.0539(4) Uani 1 1 d . . . O5 O 0.98144(13) 0.24394(9) 0.45904(10) 0.0494(4) Uani 1 1 d . . . C1 C 0.9855(2) 0.11261(14) 0.56430(15) 0.0463(5) Uani 1 1 d . . . C2 C 0.7804(2) 0.05893(16) 0.63065(17) 0.0609(6) Uani 1 1 d . . . H2A H 0.8239 0.0631 0.7001 0.073 Uiso 1 1 calc R . . H2B H 0.7818 -0.0025 0.6082 0.073 Uiso 1 1 calc R . . C3 C 0.6389(2) 0.09150(18) 0.63444(18) 0.0664(7) Uani 1 1 d . . . H3A H 0.5978 0.0917 0.5639 0.080 Uiso 1 1 calc R . . H3B H 0.5866 0.0531 0.6790 0.080 Uiso 1 1 calc R . . C4 C 0.5208(2) 0.2276(2) 0.66155(18) 0.0694(8) Uani 1 1 d . . . H4A H 0.4552 0.2082 0.7118 0.083 Uiso 1 1 calc R . . H4B H 0.4837 0.2179 0.5907 0.083 Uiso 1 1 calc R . . C5 C 0.5505(2) 0.3233(2) 0.67748(18) 0.0697(7) Uani 1 1 d . . . H5A H 0.4684 0.3578 0.6711 0.084 Uiso 1 1 calc R . . H5B H 0.5908 0.3331 0.7473 0.084 Uiso 1 1 calc R . . C6 C 0.6677(2) 0.44005(17) 0.59458(19) 0.0664(7) Uani 1 1 d . . . H6A H 0.7167 0.4587 0.6582 0.080 Uiso 1 1 calc R . . H6B H 0.5842 0.4732 0.5892 0.080 Uiso 1 1 calc R . . C7 C 0.7503(2) 0.45652(15) 0.49908(18) 0.0610(6) Uani 1 1 d . . . H7A H 0.7024 0.4362 0.4357 0.073 Uiso 1 1 calc R . . H7B H 0.7682 0.5193 0.4917 0.073 Uiso 1 1 calc R . . C8 C 0.9438(2) 0.39498(15) 0.41899(15) 0.0528(6) Uani 1 1 d . . . H8A H 0.9855 0.4496 0.3964 0.063 Uiso 1 1 calc R . . H8B H 0.8825 0.3749 0.3630 0.063 Uiso 1 1 calc R . . C9 C 1.0484(2) 0.32655(14) 0.44171(15) 0.0499(5) Uani 1 1 d . . . H9A H 1.1077 0.3214 0.3825 0.060 Uiso 1 1 calc R . . H9B H 1.1020 0.3429 0.5040 0.060 Uiso 1 1 calc R . . C10 C 1.0543(2) 0.18100(14) 0.51283(15) 0.0464(5) Uani 1 1 d . . . C11 C 1.1898(2) 0.17518(16) 0.52709(17) 0.0609(6) Uani 1 1 d . . . H11 H 1.2510 0.2145 0.4986 0.073 Uiso 1 1 calc R . . C12 C 1.0696(2) 0.05553(16) 0.61607(17) 0.0602(6) Uani 1 1 d . . . H12 H 1.0415 0.0061 0.6532 0.072 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 0.0663(4) 0.0698(5) 0.0843(5) 0.0023(3) -0.0219(4) 0.0149(3) S2 0.0569(5) 0.0487(15) 0.0509(3) 0.0068(11) -0.0091(3) -0.0132(12) S3 0.0623(12) 0.0759(7) 0.0543(10) 0.0184(7) -0.0029(7) -0.0251(9) N1 0.0554(14) 0.076(3) 0.031(4) -0.010(3) -0.023(3) 0.0058(18) N2 0.049(3) 0.052(4) 0.0407(18) 0.006(2) -0.0150(18) -0.005(2) C13 0.050(2) 0.054(2) 0.047(2) -0.0111(16) 0.0019(19) 0.0031(16) C14 0.0475(19) 0.051(2) 0.041(2) -0.0155(15) -0.0001(17) 0.0046(16) S3A 0.0623(12) 0.0759(7) 0.0543(10) 0.0184(7) -0.0029(7) -0.0251(9) S2A 0.0569(5) 0.0487(15) 0.0509(3) 0.0068(11) -0.0091(3) -0.0132(12) N1A 0.0554(14) 0.076(3) 0.031(4) -0.010(3) -0.023(3) 0.0058(18) N2A 0.049(3) 0.052(4) 0.0407(18) 0.006(2) -0.0150(18) -0.005(2) C13A 0.031(4) 0.031(5) 0.020(4) 0.000(3) -0.009(4) -0.005(3) C14A 0.029(4) 0.035(5) 0.016(4) -0.004(3) -0.005(4) 0.001(4) O1 0.0551(9) 0.0541(10) 0.0482(8) 0.0120(7) -0.0045(7) -0.0086(7) O2 0.0511(9) 0.0734(12) 0.0533(8) 0.0032(8) -0.0093(7) -0.0068(8) O3 0.0546(9) 0.0592(11) 0.0476(8) -0.0012(7) 0.0033(7) -0.0002(7) O4 0.0554(9) 0.0587(10) 0.0472(8) 0.0013(7) -0.0053(7) 0.0066(7) O5 0.0482(8) 0.0462(9) 0.0534(8) 0.0061(7) -0.0080(7) -0.0031(7) C1 0.0518(13) 0.0441(14) 0.0424(11) -0.0071(9) -0.0083(10) 0.0004(10) C2 0.0787(17) 0.0493(15) 0.0543(13) 0.0068(11) -0.0040(12) -0.0185(13) C3 0.0690(16) 0.0751(19) 0.0549(13) 0.0090(12) -0.0018(12) -0.0332(14) C4 0.0455(14) 0.106(2) 0.0564(14) 0.0183(14) 0.0020(11) -0.0088(14) C5 0.0546(14) 0.095(2) 0.0595(14) 0.0075(14) 0.0093(12) 0.0131(14) C6 0.0650(15) 0.0597(18) 0.0742(16) -0.0157(13) -0.0017(13) 0.0106(13) C7 0.0636(14) 0.0434(15) 0.0757(15) 0.0036(12) -0.0050(13) 0.0034(12) C8 0.0603(14) 0.0534(16) 0.0448(11) 0.0084(10) 0.0010(10) -0.0039(11) C9 0.0509(12) 0.0530(15) 0.0457(11) 0.0054(10) 0.0015(10) -0.0080(11) C10 0.0527(12) 0.0436(14) 0.0422(11) -0.0041(9) -0.0090(10) 0.0033(10) C11 0.0516(13) 0.0618(17) 0.0688(14) 0.0033(12) -0.0081(11) 0.0009(12) C12 0.0787(16) 0.0426(14) 0.0584(13) 0.0029(10) -0.0122(12) 0.0015(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 C12 1.705(2) . ? S1 C11 1.713(2) . ? S2 C14 1.728(5) . ? S3 C13 1.703(4) . ? N1 C13 1.403(10) . ? N1 H1N1 0.72(3) . ? N1 H2N1 0.75(4) . ? N2 C14 1.320(8) . ? N2 H1N2 0.82(3) . ? N2 H2N2 0.82(3) . ? C13 C14 1.508(5) . ? S3A C13A 1.524(12) . ? S2A C14A 1.518(16) . ? N1A C14A 1.30(4) . ? N1A H1N1 0.88(5) . ? N1A H2N1 0.88(5) . ? N2A C13A 1.27(3) . ? N2A H1N2 1.19(4) . ? N2A H2N2 0.44(4) . ? C13A C14A 1.591(12) . ? C13A H2N2 1.50(4) . ? C14A H2N1 1.53(4) . ? O1 C1 1.363(2) . ? O1 C2 1.424(2) . ? O2 C3 1.418(3) . ? O2 C4 1.420(3) . ? O3 C6 1.407(3) . ? O3 C5 1.415(3) . ? O4 C7 1.419(2) . ? O4 C8 1.419(2) . ? O5 C10 1.365(2) . ? O5 C9 1.434(2) . ? C1 C12 1.357(3) . ? C1 C10 1.409(3) . ? C2 C3 1.493(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.488(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.502(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.489(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.357(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? 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 C12 S1 C11 91.95(11) . . ? C13 N1 H1N1 109(3) . . ? C13 N1 H2N1 130(3) . . ? H1N1 N1 H2N1 121(4) . . ? C14 N2 H1N2 114(2) . . ? C14 N2 H2N2 125(3) . . ? H1N2 N2 H2N2 121(3) . . ? N1 C13 C14 110.7(6) . . ? N1 C13 S3 127.1(6) . . ? C14 C13 S3 122.3(3) . . ? N2 C14 C13 115.4(4) . . ? N2 C14 S2 123.7(3) . . ? C13 C14 S2 120.8(3) . . ? C14A N1A H1N1 154(5) . . ? C14A N1A H2N1 86(4) . . ? H1N1 N1A H2N1 93(5) . . ? C13A N2A H1N2 131(3) . . ? C13A N2A H2N2 113(8) . . ? H1N2 N2A H2N2 113(7) . . ? N2A C13A S3A 123.0(10) . . ? N2A C13A C14A 116.8(11) . . ? S3A C13A C14A 117.7(7) . . ? N2A C13A H2N2 15.8(19) . . ? S3A C13A H2N2 108.9(16) . . ? C14A C13A H2N2 132.3(16) . . ? N1A C14A S2A 144.3(19) . . ? N1A C14A C13A 99.7(19) . . ? S2A C14A C13A 115.8(8) . . ? N1A C14A H2N1 35(2) . . ? S2A C14A H2N1 110.4(15) . . ? C13A C14A H2N1 133.4(15) . . ? C1 O1 C2 116.54(15) . . ? C3 O2 C4 115.24(18) . . ? C6 O3 C5 114.55(19) . . ? C7 O4 C8 114.57(16) . . ? C10 O5 C9 116.08(15) . . ? C12 C1 O1 129.6(2) . . ? C12 C1 C10 112.8(2) . . ? O1 C1 C10 117.64(17) . . ? O1 C2 C3 107.36(19) . . ? O1 C2 H2A 110.2 . . ? C3 C2 H2A 110.2 . . ? O1 C2 H2B 110.2 . . ? C3 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? O2 C3 C2 107.98(18) . . ? O2 C3 H3A 110.1 . . ? C2 C3 H3A 110.1 . . ? O2 C3 H3B 110.1 . . ? C2 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? O2 C4 C5 108.92(18) . . ? O2 C4 H4A 109.9 . . ? C5 C4 H4A 109.9 . . ? O2 C4 H4B 109.9 . . ? C5 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? O3 C5 C4 107.1(2) . . ? O3 C5 H5A 110.3 . . ? C4 C5 H5A 110.3 . . ? O3 C5 H5B 110.3 . . ? C4 C5 H5B 110.3 . . ? H5A C5 H5B 108.5 . . ? O3 C6 C7 107.47(18) . . ? O3 C6 H6A 110.2 . . ? C7 C6 H6A 110.2 . . ? O3 C6 H6B 110.2 . . ? C7 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? O4 C7 C6 107.66(18) . . ? O4 C7 H7A 110.2 . . ? C6 C7 H7A 110.2 . . ? O4 C7 H7B 110.2 . . ? C6 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? O4 C8 C9 107.75(16) . . ? O4 C8 H8A 110.2 . . ? C9 C8 H8A 110.2 . . ? O4 C8 H8B 110.2 . . ? C9 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? O5 C9 C8 107.93(16) . . ? O5 C9 H9A 110.1 . . ? C8 C9 H9A 110.1 . . ? O5 C9 H9B 110.1 . . ? C8 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? C11 C10 O5 128.5(2) . . ? C11 C10 C1 112.66(19) . . ? O5 C10 C1 118.85(18) . . ? C10 C11 S1 111.18(18) . . ? C10 C11 H11 124.4 . . ? S1 C11 H11 124.4 . . ? C1 C12 S1 111.41(18) . . ? C1 C12 H12 124.3 . . ? S1 C12 H12 124.3 . . ? 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 N1 C13 C14 N2 178.5(6) . . . . ? S3 C13 C14 N2 -2.1(5) . . . . ? N1 C13 C14 S2 -4.4(5) . . . . ? S3 C13 C14 S2 175.0(3) . . . . ? N2A C13A C14A N1A 173(2) . . . . ? S3A C13A C14A N1A -24.8(15) . . . . ? N2A C13A C14A S2A -3.6(18) . . . . ? S3A C13A C14A S2A 158.9(8) . . . . ? C2 O1 C1 C12 15.0(3) . . . . ? C2 O1 C1 C10 -163.97(18) . . . . ? C1 O1 C2 C3 161.05(17) . . . . ? C4 O2 C3 C2 165.19(17) . . . . ? O1 C2 C3 O2 -64.8(2) . . . . ? C3 O2 C4 C5 -162.39(18) . . . . ? C6 O3 C5 C4 173.07(17) . . . . ? O2 C4 C5 O3 62.7(2) . . . . ? C5 O3 C6 C7 -173.10(17) . . . . ? C8 O4 C7 C6 161.42(18) . . . . ? O3 C6 C7 O4 -62.1(2) . . . . ? C7 O4 C8 C9 -165.78(17) . . . . ? C10 O5 C9 C8 -159.87(16) . . . . ? O4 C8 C9 O5 68.4(2) . . . . ? C9 O5 C10 C11 -20.0(3) . . . . ? C9 O5 C10 C1 158.17(17) . . . . ? C12 C1 C10 C11 -0.5(3) . . . . ? O1 C1 C10 C11 178.66(17) . . . . ? C12 C1 C10 O5 -178.97(17) . . . . ? O1 C1 C10 O5 0.2(3) . . . . ? O5 C10 C11 S1 177.98(16) . . . . ? C1 C10 C11 S1 -0.3(2) . . . . ? C12 S1 C11 C10 0.77(18) . . . . ? O1 C1 C12 S1 -177.96(16) . . . . ? C10 C1 C12 S1 1.1(2) . . . . ? C11 S1 C12 C1 -1.06(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 N1 H1N1 O1 0.72(3) 2.47(3) 3.048(8) 138(4) 4_666 N1 H1N1 O5 0.72(3) 2.56(3) 3.140(12) 139(4) 4_666 N1 H2N1 O3 0.75(4) 2.28(3) 2.993(12) 159(4) 4_666 N2 H1N2 O2 0.82(3) 2.29(3) 3.097(5) 173(3) . N2 H2N2 O4 0.82(3) 2.46(3) 3.175(6) 147(4) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.186 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.038 # Attachment 'bas5.cif' data_bas5 #TrackingRef 'C004680A_ccdc_771037_771042_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 771041' #TrackingRef 'bas5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3,5,6,8,9,11,12-octahydronaphtho[2,3-b][1,4,7,10,13] pentaoxacyclopentadecine ethanebis(thioamide) clathrate ; _chemical_name_common ; 2,3,5,6,8,9,11,12-octahydronaphtho(2,3-b)(1,4,7,10,13) pentaoxacyclopentadecine ethanebis(thioamide) clathrate ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 O5, C2 H4 N2 S2' _chemical_formula_sum 'C20 H26 N2 O5 S2' _chemical_formula_weight 438.55 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' O O 0.0106 0.0060 '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/m' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 7.965(2) _cell_length_b 10.521(2) _cell_length_c 13.080(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.68(2) _cell_angle_gamma 90.00 _cell_volume 1093.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11522 _cell_measurement_theta_min 1.94 _cell_measurement_theta_max 27.86 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.276 _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 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 'Nonius KappaCCD' _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 11441 _diffrn_reflns_av_R_equivalents 0.0661 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2617 _reflns_number_gt 1655 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2001)' _computing_cell_refinement 'DENZO SMN (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO SMN (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics MERCURY _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^)+(0.0678P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.050(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2617 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0707 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 0.67339(8) 0.2500 0.57587(5) 0.0541(2) Uani 1 2 d S . . S2 S 0.67359(9) 0.2500 0.90546(6) 0.0917(4) Uani 1 2 d S . . O1 O 0.14243(13) 0.12818(10) 0.59623(8) 0.0463(3) Uani 1 1 d . . . O2 O 0.20379(14) 0.03711(13) 0.79373(9) 0.0569(4) Uani 1 1 d . . . O3 O 0.1540(2) 0.2500 0.90600(14) 0.0690(6) Uani 1 2 d S . . N1 N 0.8947(3) 0.2500 0.73527(19) 0.0620(7) Uani 1 2 d S . . H1A H 0.916(4) 0.2500 0.801(2) 0.074 Uiso 1 2 d S . . H1B H 0.966(4) 0.2500 0.696(2) 0.074 Uiso 1 2 d S . . N2 N 0.4543(2) 0.2500 0.7450(2) 0.0589(6) Uani 1 2 d S . . H2A H 0.436(3) 0.2500 0.676(2) 0.071 Uiso 1 2 d S . . H2B H 0.377(4) 0.2500 0.782(2) 0.071 Uiso 1 2 d S . . C1 C 0.20592(17) 0.18258(15) 0.51160(12) 0.0380(4) Uani 1 1 d . . . C2 C 0.1798(2) -0.00293(17) 0.61521(13) 0.0514(5) Uani 1 1 d . . . H21 H 0.3001 -0.0172 0.6157 0.062 Uiso 1 1 calc R . . H22 H 0.1248 -0.0554 0.5620 0.062 Uiso 1 1 calc R . . C3 C 0.1169(3) -0.0361(2) 0.71721(14) 0.0605(5) Uani 1 1 d . . . H3A H -0.0028 -0.0191 0.7170 0.073 Uiso 1 1 calc R . . H3B H 0.1349 -0.1258 0.7310 0.073 Uiso 1 1 calc R . . C4 C 0.1375(2) 0.0284(2) 0.89108(14) 0.0667(6) Uani 1 1 d . . . H4A H 0.1687 -0.0522 0.9229 0.080 Uiso 1 1 calc R . . H4B H 0.0158 0.0338 0.8844 0.080 Uiso 1 1 calc R . . C5 C 0.2084(2) 0.1361(2) 0.95511(14) 0.0668(6) Uani 1 1 d . . . H5A H 0.1683 0.1320 1.0235 0.080 Uiso 1 1 calc R . . H5B H 0.3303 0.1320 0.9605 0.080 Uiso 1 1 calc R . . C6 C 0.26981(18) 0.11736(16) 0.43282(12) 0.0429(4) Uani 1 1 d . . . H6 H 0.2695 0.0290 0.4334 0.052 Uiso 1 1 calc R . . C7 C 0.33675(18) 0.18317(16) 0.35004(12) 0.0423(4) Uani 1 1 d . . . C8 C 0.4058(2) 0.1186(2) 0.26757(13) 0.0558(5) Uani 1 1 d . . . H8 H 0.4061 0.0302 0.2665 0.067 Uiso 1 1 calc R . . C9 C 0.4720(2) 0.1842(2) 0.18962(14) 0.0655(6) Uani 1 1 d . . . H9 H 0.5174 0.1402 0.1362 0.079 Uiso 1 1 calc R . . C10 C 0.7378(3) 0.2500 0.69887(18) 0.0435(6) Uani 1 2 d S . . C11 C 0.6108(3) 0.2500 0.78246(19) 0.0490(6) Uani 1 2 d S . . 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 0.0570(4) 0.0613(5) 0.0432(4) 0.000 -0.0025(3) 0.000 S2 0.0503(4) 0.1802(11) 0.0451(5) 0.000 0.0070(3) 0.000 O1 0.0510(6) 0.0435(7) 0.0451(7) 0.0065(5) 0.0085(5) 0.0017(5) O2 0.0504(7) 0.0755(9) 0.0449(7) 0.0108(6) 0.0043(5) -0.0110(6) O3 0.0593(11) 0.0903(16) 0.0555(12) 0.000 -0.0117(9) 0.000 N1 0.0335(11) 0.103(2) 0.0499(14) 0.000 0.0054(9) 0.000 N2 0.0328(11) 0.0843(18) 0.0599(15) 0.000 0.0046(10) 0.000 C1 0.0334(8) 0.0423(9) 0.0377(9) 0.0018(7) -0.0023(6) -0.0025(6) C2 0.0599(11) 0.0415(11) 0.0522(11) 0.0069(8) -0.0014(8) -0.0050(8) C3 0.0666(11) 0.0564(12) 0.0580(12) 0.0150(10) -0.0001(9) -0.0144(9) C4 0.0604(11) 0.0900(16) 0.0504(12) 0.0231(11) 0.0087(9) -0.0087(10) C5 0.0570(11) 0.1019(18) 0.0418(11) 0.0161(11) 0.0048(8) -0.0042(10) C6 0.0442(9) 0.0397(10) 0.0443(10) -0.0028(8) -0.0016(7) -0.0011(7) C7 0.0366(8) 0.0526(10) 0.0368(9) -0.0030(7) -0.0040(6) 0.0013(6) C8 0.0559(10) 0.0647(13) 0.0464(11) -0.0108(9) -0.0001(8) 0.0066(8) C9 0.0545(11) 0.1020(16) 0.0400(10) -0.0091(10) 0.0039(8) 0.0062(9) C10 0.0394(12) 0.0402(14) 0.0508(15) 0.000 0.0030(10) 0.000 C11 0.0369(12) 0.0547(16) 0.0556(16) 0.000 0.0033(10) 0.000 _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 C10 1.657(2) . ? S2 C11 1.654(3) . ? O1 C1 1.3714(18) . ? O1 C2 1.429(2) . ? O2 C3 1.409(2) . ? O2 C4 1.412(2) . ? O3 C5 1.415(2) 4_565 ? O3 C5 1.415(2) . ? N1 C10 1.308(3) . ? N1 H1A 0.86(3) . ? N1 H1B 0.79(3) . ? N2 C11 1.309(3) . ? N2 H2A 0.90(3) . ? N2 H2B 0.81(3) . ? C1 C6 1.363(2) . ? C1 C1 1.419(3) 4_565 ? C2 C3 1.496(2) . ? C2 H21 0.9700 . ? C2 H22 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.498(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.418(2) . ? C6 H6 0.9300 . ? C7 C7 1.406(3) 4_565 ? C7 C8 1.416(2) . ? C8 C9 1.365(3) . ? C8 H8 0.9300 . ? C9 C9 1.385(4) 4_565 ? C9 H9 0.9300 . ? C10 C11 1.536(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 C1 O1 C2 117.35(12) . . ? C3 O2 C4 114.20(14) . . ? C5 O3 C5 115.8(2) 4_565 . ? C10 N1 H1A 119(2) . . ? C10 N1 H1B 118(2) . . ? H1A N1 H1B 123(3) . . ? C11 N2 H2A 117.4(18) . . ? C11 N2 H2B 121(2) . . ? H2A N2 H2B 122(3) . . ? C6 C1 O1 125.09(15) . . ? C6 C1 C1 120.22(10) . 4_565 ? O1 C1 C1 114.67(8) . 4_565 ? O1 C2 C3 107.58(15) . . ? O1 C2 H21 110.2 . . ? C3 C2 H21 110.2 . . ? O1 C2 H22 110.2 . . ? C3 C2 H22 110.2 . . ? H21 C2 H22 108.5 . . ? O2 C3 C2 109.19(14) . . ? O2 C3 H3A 109.8 . . ? C2 C3 H3A 109.8 . . ? O2 C3 H3B 109.8 . . ? C2 C3 H3B 109.8 . . ? H3A C3 H3B 108.3 . . ? O2 C4 C5 107.79(15) . . ? O2 C4 H4A 110.1 . . ? C5 C4 H4A 110.1 . . ? O2 C4 H4B 110.1 . . ? C5 C4 H4B 110.1 . . ? H4A C4 H4B 108.5 . . ? O3 C5 C4 107.08(16) . . ? O3 C5 H5A 110.3 . . ? C4 C5 H5A 110.3 . . ? O3 C5 H5B 110.3 . . ? C4 C5 H5B 110.3 . . ? H5A C5 H5B 108.6 . . ? C1 C6 C7 120.54(16) . . ? C1 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C7 C7 C8 118.68(11) 4_565 . ? C7 C7 C6 119.23(9) 4_565 . ? C8 C7 C6 122.08(17) . . ? C9 C8 C7 120.96(19) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C9 120.36(12) . 4_565 ? C8 C9 H9 119.8 . . ? C9 C9 H9 119.8 4_565 . ? N1 C10 C11 113.5(2) . . ? N1 C10 S1 125.60(19) . . ? C11 C10 S1 120.95(16) . . ? N2 C11 C10 112.8(2) . . ? N2 C11 S2 125.8(2) . . ? C10 C11 S2 121.36(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 O1 C1 C6 14.9(2) . . . . ? C2 O1 C1 C1 -163.33(10) . . . 4_565 ? C1 O1 C2 C3 172.95(13) . . . . ? C4 O2 C3 C2 170.78(16) . . . . ? O1 C2 C3 O2 -62.5(2) . . . . ? C3 O2 C4 C5 -164.24(16) . . . . ? C5 O3 C5 C4 -179.97(12) 4_565 . . . ? O2 C4 C5 O3 61.6(2) . . . . ? O1 C1 C6 C7 -178.24(13) . . . . ? C1 C1 C6 C7 -0.06(16) 4_565 . . . ? C1 C6 C7 C7 0.06(16) . . . 4_565 ? C1 C6 C7 C8 179.28(14) . . . . ? C7 C7 C8 C9 0.3(2) 4_565 . . . ? C6 C7 C8 C9 -178.90(15) . . . . ? C7 C8 C9 C9 -0.3(2) . . . 4_565 ? N1 C10 C11 N2 180.0 . . . . ? S1 C10 C11 N2 0.0 . . . . ? N1 C10 C11 S2 0.0 . . . . ? S1 C10 C11 S2 180.0 . . . . ? 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 N1 H1A O3 0.86(3) 2.27(3) 2.943(3) 135(2) 1_655 N1 H1B O1 0.79(3) 2.35(3) 3.051(2) 147.0(4) 4_665 N1 H1B O1 0.79(3) 2.35(3) 3.051(2) 147.0(4) 1_655 N2 H2B O3 0.81(3) 2.48(3) 3.287(3) 176(3) . _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.306 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.043 # Attachment 'bas6r.cif' data_bas6r _database_code_depnum_ccdc_archive 'CCDC 771042' #TrackingRef 'bas6r.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3,5,6,8,9,11,12-octahydronaphtho[2,3-b] [1,4,7,10,13]pentaoxacyclopentadecine 1,2,5-oxadiazole-3,4-diamine monohydrate ; _chemical_name_common ; 2,3,5,6,8,9,11,12-octahydronaphtho(2,3-b) (1,4,7,10,13)pentaoxacyclopentadecine 1,2,5-oxadiazole-3,4-diamine monohydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 O5, C2 H4 N4 O, H2 O' _chemical_formula_sum 'C20 H28 N4 O7' _chemical_formula_weight 436.46 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' _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 10.536(2) _cell_length_b 15.585(4) _cell_length_c 13.639(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.17(2) _cell_angle_gamma 90.00 _cell_volume 2239.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 16499 _cell_measurement_theta_min 1.93 _cell_measurement_theta_max 25.0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.099 _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 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 'Nonis KappaCCD' _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 16152 _diffrn_reflns_av_R_equivalents 0.1072 _diffrn_reflns_av_sigmaI/netI 0.1049 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.28 _reflns_number_total 3788 _reflns_number_gt 1560 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics MERCURY _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. Two SADI restraints were applied to N-H distances in two amino-groups of 1,2,5-oxadiazole-3,4-diamine molecule. ; _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^)+(0.0139P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0109(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3788 _refine_ls_number_parameters 299 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1325 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0616 _refine_ls_goodness_of_fit_ref 0.846 _refine_ls_restrained_S_all 0.847 _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 O1 O 0.34939(12) 0.29357(10) 0.11321(11) 0.0651(5) Uani 1 1 d . . . O2 O 0.39774(15) 0.17346(12) -0.02872(13) 0.0787(5) Uani 1 1 d . . . O3 O 0.16357(16) 0.08757(10) -0.05127(12) 0.0818(5) Uani 1 1 d . . . O4 O -0.01881(14) 0.21094(12) -0.00638(13) 0.0745(5) Uani 1 1 d . . . O5 O 0.10931(12) 0.31585(10) 0.12292(11) 0.0664(5) Uani 1 1 d . . . O6 O 0.31580(14) 0.58905(13) -0.29381(17) 0.0855(6) Uani 1 1 d . . . N1 N 0.1967(2) 0.3821(2) -0.30236(18) 0.0894(9) Uani 1 1 d D . . H1N1 H 0.210(3) 0.363(2) -0.3575(17) 0.134 Uiso 1 1 d D . . H2N1 H 0.204(3) 0.3471(18) -0.255(2) 0.134 Uiso 1 1 d D . . N2 N 0.2026(2) 0.46692(16) -0.10239(19) 0.0827(8) Uani 1 1 d D . . H1N2 H 0.221(2) 0.4969(17) -0.0506(17) 0.124 Uiso 1 1 d D . . H2N2 H 0.205(2) 0.4070(13) -0.107(2) 0.124 Uiso 1 1 d D . . N3 N 0.28797(16) 0.57880(15) -0.19469(18) 0.0698(6) Uani 1 1 d . . . N4 N 0.28766(19) 0.51338(18) -0.34511(17) 0.0812(7) Uani 1 1 d . . . C1 C 0.31323(19) 0.37714(17) 0.12533(16) 0.0549(7) Uani 1 1 d . . . C2 C 0.47651(17) 0.27911(16) 0.08046(18) 0.0731(8) Uani 1 1 d . . . H2A H 0.5374 0.2908 0.1331 0.088 Uiso 1 1 calc R . . H2B H 0.4949 0.3164 0.0256 0.088 Uiso 1 1 calc R . . C3 C 0.4841(2) 0.18725(17) 0.0500(2) 0.0782(8) Uani 1 1 d . . . H3A H 0.5696 0.1738 0.0300 0.094 Uiso 1 1 calc R . . H3B H 0.4632 0.1503 0.1046 0.094 Uiso 1 1 calc R . . C4 C 0.3877(2) 0.08563(18) -0.0574(2) 0.0847(8) Uani 1 1 d . . . H4A H 0.3890 0.0492 0.0003 0.102 Uiso 1 1 calc R . . H4B H 0.4590 0.0701 -0.0976 0.102 Uiso 1 1 calc R . . C5 C 0.2672(2) 0.07306(17) -0.11362(19) 0.0921(9) Uani 1 1 d . . . H5A H 0.2631 0.1127 -0.1685 0.110 Uiso 1 1 calc R . . H5B H 0.2633 0.0151 -0.1393 0.110 Uiso 1 1 calc R . . C6 C 0.0448(3) 0.09340(17) -0.1011(2) 0.0928(9) Uani 1 1 d . . . H6A H 0.0197 0.0377 -0.1265 0.111 Uiso 1 1 calc R . . H6B H 0.0499 0.1332 -0.1556 0.111 Uiso 1 1 calc R . . C7 C -0.0491(2) 0.12449(18) -0.0288(2) 0.0907(9) Uani 1 1 d . . . H7A H -0.1345 0.1207 -0.0564 0.109 Uiso 1 1 calc R . . H7B H -0.0446 0.0897 0.0302 0.109 Uiso 1 1 calc R . . C8 C -0.07568(19) 0.24009(17) 0.0796(2) 0.0844(9) Uani 1 1 d . . . H8A H -0.0575 0.2005 0.1330 0.101 Uiso 1 1 calc R . . H8B H -0.1670 0.2432 0.0699 0.101 Uiso 1 1 calc R . . C9 C -0.02463(18) 0.32633(16) 0.10431(19) 0.0780(8) Uani 1 1 d . . . H9A H -0.0395 0.3657 0.0502 0.094 Uiso 1 1 calc R . . H9B H -0.0655 0.3490 0.1619 0.094 Uiso 1 1 calc R . . C10 C 0.17936(19) 0.38960(17) 0.13049(16) 0.0567(7) Uani 1 1 d . . . C11 C 0.1316(2) 0.47023(17) 0.14158(15) 0.0616(7) Uani 1 1 d . . . H11 H 0.0441 0.4781 0.1436 0.074 Uiso 1 1 calc R . . C12 C 0.2126(2) 0.54190(18) 0.15000(16) 0.0584(7) Uani 1 1 d . . . C13 C 0.1662(2) 0.62559(19) 0.16411(18) 0.0745(8) Uani 1 1 d . . . H13 H 0.0791 0.6344 0.1671 0.089 Uiso 1 1 calc R . . C14 C 0.2459(3) 0.69395(18) 0.17352(19) 0.0870(9) Uani 1 1 d . . . H14 H 0.2130 0.7487 0.1827 0.104 Uiso 1 1 calc R . . C15 C 0.3775(3) 0.68200(19) 0.16938(19) 0.0855(8) Uani 1 1 d . . . H15 H 0.4320 0.7287 0.1756 0.103 Uiso 1 1 calc R . . C16 C 0.4251(2) 0.60204(19) 0.15634(18) 0.0758(8) Uani 1 1 d . . . H16 H 0.5126 0.5947 0.1542 0.091 Uiso 1 1 calc R . . C17 C 0.3455(2) 0.52969(18) 0.14599(16) 0.0606(7) Uani 1 1 d . . . C18 C 0.39231(19) 0.44531(17) 0.13264(16) 0.0624(7) Uani 1 1 d . . . H18 H 0.4794 0.4366 0.1288 0.075 Uiso 1 1 calc R . . C19 C 0.2436(2) 0.46109(19) -0.2808(2) 0.0594(7) Uani 1 1 d . . . C20 C 0.24590(19) 0.50128(19) -0.1876(2) 0.0551(7) Uani 1 1 d . . . O1W O 0.19764(15) 0.28481(13) -0.10144(15) 0.0890(6) Uani 1 1 d . . . H1W H 0.263(2) 0.2571(18) -0.085(2) 0.134 Uiso 1 1 d . . . H2W H 0.133(2) 0.2631(18) -0.074(2) 0.134 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 O1 0.0498(9) 0.0692(13) 0.0763(13) -0.0005(9) 0.0057(8) 0.0093(8) O2 0.0846(11) 0.0735(15) 0.0780(14) -0.0013(12) -0.0001(10) 0.0162(11) O3 0.0857(12) 0.0937(15) 0.0659(13) 0.0006(10) 0.0008(10) 0.0145(10) O4 0.0749(11) 0.0696(14) 0.0790(15) -0.0071(11) -0.0017(9) -0.0032(9) O5 0.0445(9) 0.0776(14) 0.0771(13) -0.0058(10) 0.0014(8) 0.0032(8) O6 0.0859(11) 0.0765(16) 0.0946(18) 0.0161(14) 0.0126(11) -0.0079(10) N1 0.0994(15) 0.085(2) 0.084(2) -0.0178(17) 0.0057(17) -0.0110(15) N2 0.1007(15) 0.084(2) 0.063(2) 0.0030(17) 0.0046(14) 0.0022(16) N3 0.0629(12) 0.0694(18) 0.077(2) -0.0047(15) 0.0047(11) 0.0016(12) N4 0.0910(15) 0.084(2) 0.0684(18) -0.0050(16) 0.0051(12) -0.0096(13) C1 0.0490(15) 0.065(2) 0.0504(17) 0.0021(14) -0.0011(11) 0.0092(13) C2 0.0454(14) 0.082(2) 0.092(2) 0.0007(17) 0.0043(12) 0.0103(13) C3 0.0564(14) 0.082(2) 0.096(2) 0.0066(19) 0.0045(15) 0.0153(14) C4 0.0919(19) 0.082(2) 0.081(2) -0.0092(18) 0.0194(16) 0.0214(17) C5 0.112(2) 0.094(2) 0.071(2) -0.0179(18) 0.0150(19) 0.0067(17) C6 0.103(2) 0.080(2) 0.095(3) -0.0080(18) -0.026(2) 0.0025(17) C7 0.0864(19) 0.074(2) 0.111(3) -0.005(2) -0.0155(18) -0.0076(17) C8 0.0522(15) 0.095(3) 0.106(3) -0.006(2) 0.0065(15) -0.0046(15) C9 0.0460(15) 0.089(2) 0.099(2) -0.0175(17) 0.0037(13) 0.0027(13) C10 0.0486(15) 0.075(2) 0.0461(17) -0.0023(15) -0.0011(11) 0.0019(14) C11 0.0509(14) 0.080(2) 0.0535(18) -0.0040(15) 0.0007(11) 0.0110(15) C12 0.0649(16) 0.066(2) 0.0444(17) -0.0027(14) -0.0007(12) 0.0072(14) C13 0.0808(18) 0.076(2) 0.067(2) -0.0053(17) 0.0038(15) 0.0107(17) C14 0.106(2) 0.073(3) 0.082(2) -0.0049(18) 0.0060(18) 0.0122(18) C15 0.102(2) 0.075(2) 0.080(2) -0.0010(18) -0.0006(16) -0.0087(17) C16 0.0707(16) 0.078(2) 0.078(2) 0.0037(18) -0.0050(14) -0.0061(17) C17 0.0589(16) 0.072(2) 0.0506(18) 0.0007(15) -0.0027(12) 0.0016(14) C18 0.0453(13) 0.078(2) 0.0634(19) 0.0020(15) -0.0006(11) 0.0026(14) C19 0.0501(14) 0.062(2) 0.066(2) -0.0061(19) 0.0000(13) 0.0019(13) C20 0.0439(13) 0.059(2) 0.062(2) 0.0006(18) -0.0009(13) 0.0069(12) O1W 0.0954(14) 0.0804(16) 0.0913(16) 0.0237(11) 0.0035(12) 0.0079(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 C1 1.368(2) . ? O1 C2 1.438(2) . ? O2 C3 1.409(3) . ? O2 C4 1.427(3) . ? O3 C6 1.415(2) . ? O3 C5 1.415(2) . ? O4 C8 1.404(3) . ? O4 C7 1.416(3) . ? O5 C10 1.369(2) . ? O5 C9 1.438(2) . ? O6 N3 1.398(2) . ? O6 N4 1.400(2) . ? N1 C19 1.357(3) . ? N1 H1N1 0.82(2) . ? N1 H2N1 0.85(2) . ? N2 C20 1.367(3) . ? N2 H1N2 0.867(18) . ? N2 H2N2 0.936(19) . ? N3 C20 1.291(3) . ? N4 C19 1.291(3) . ? C1 C18 1.353(3) . ? C1 C10 1.427(3) . ? C2 C3 1.493(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.483(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.492(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.484(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.363(3) . ? C11 C12 1.409(3) . ? C11 H11 0.9300 . ? C12 C13 1.407(3) . ? C12 C17 1.415(3) . ? C13 C14 1.361(3) . ? C13 H13 0.9300 . ? C14 C15 1.401(3) . ? C14 H14 0.9300 . ? C15 C16 1.356(3) . ? C15 H15 0.9300 . ? C16 C17 1.411(3) . ? C16 H16 0.9300 . ? C17 C18 1.418(3) . ? C18 H18 0.9300 . ? C19 C20 1.417(3) . ? O1W H1W 0.84(2) . ? O1W H2W 0.86(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C2 116.75(17) . . ? C3 O2 C4 113.5(2) . . ? C6 O3 C5 114.0(2) . . ? C8 O4 C7 112.9(2) . . ? C10 O5 C9 116.34(18) . . ? N3 O6 N4 109.91(18) . . ? C19 N1 H1N1 117(2) . . ? C19 N1 H2N1 113(2) . . ? H1N1 N1 H2N1 117(3) . . ? C20 N2 H1N2 114(2) . . ? C20 N2 H2N2 109.3(18) . . ? H1N2 N2 H2N2 126(3) . . ? C20 N3 O6 105.0(2) . . ? C19 N4 O6 105.5(2) . . ? C18 C1 O1 125.7(2) . . ? C18 C1 C10 119.8(2) . . ? O1 C1 C10 114.4(2) . . ? O1 C2 C3 106.98(18) . . ? O1 C2 H2A 110.3 . . ? C3 C2 H2A 110.3 . . ? O1 C2 H2B 110.3 . . ? C3 C2 H2B 110.3 . . ? H2A C2 H2B 108.6 . . ? O2 C3 C2 108.7(2) . . ? O2 C3 H3A 109.9 . . ? C2 C3 H3A 109.9 . . ? O2 C3 H3B 109.9 . . ? C2 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? O2 C4 C5 109.0(2) . . ? O2 C4 H4A 109.9 . . ? C5 C4 H4A 109.9 . . ? O2 C4 H4B 109.9 . . ? C5 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? O3 C5 C4 109.3(2) . . ? O3 C5 H5A 109.8 . . ? C4 C5 H5A 109.8 . . ? O3 C5 H5B 109.8 . . ? C4 C5 H5B 109.8 . . ? H5A C5 H5B 108.3 . . ? O3 C6 C7 107.2(2) . . ? O3 C6 H6A 110.3 . . ? C7 C6 H6A 110.3 . . ? O3 C6 H6B 110.3 . . ? C7 C6 H6B 110.3 . . ? H6A C6 H6B 108.5 . . ? O4 C7 C6 107.6(2) . . ? O4 C7 H7A 110.2 . . ? C6 C7 H7A 110.2 . . ? O4 C7 H7B 110.2 . . ? C6 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? O4 C8 C9 108.9(2) . . ? O4 C8 H8A 109.9 . . ? C9 C8 H8A 109.9 . . ? O4 C8 H8B 109.9 . . ? C9 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? O5 C9 C8 106.68(19) . . ? O5 C9 H9A 110.4 . . ? C8 C9 H9A 110.4 . . ? O5 C9 H9B 110.4 . . ? C8 C9 H9B 110.4 . . ? H9A C9 H9B 108.6 . . ? C11 C10 O5 125.6(2) . . ? C11 C10 C1 119.9(2) . . ? O5 C10 C1 114.5(2) . . ? C10 C11 C12 121.0(2) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C13 C12 C11 122.3(2) . . ? C13 C12 C17 118.5(2) . . ? C11 C12 C17 119.3(2) . . ? C14 C13 C12 121.5(2) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 120.1(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 119.7(3) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 121.8(2) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C16 C17 C12 118.4(2) . . ? C16 C17 C18 123.2(2) . . ? C12 C17 C18 118.5(2) . . ? C1 C18 C17 121.5(2) . . ? C1 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? N4 C19 N1 124.1(3) . . ? N4 C19 C20 109.3(3) . . ? N1 C19 C20 126.5(3) . . ? N3 C20 N2 123.5(3) . . ? N3 C20 C19 110.2(3) . . ? N2 C20 C19 126.1(3) . . ? H1W O1W H2W 109(3) . . ? 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 N4 O6 N3 C20 0.1(2) . . . . ? N3 O6 N4 C19 0.9(2) . . . . ? C2 O1 C1 C18 -17.0(3) . . . . ? C2 O1 C1 C10 163.16(18) . . . . ? C1 O1 C2 C3 -166.8(2) . . . . ? C4 O2 C3 C2 -174.02(19) . . . . ? O1 C2 C3 O2 62.1(2) . . . . ? C3 O2 C4 C5 160.4(2) . . . . ? C6 O3 C5 C4 168.6(2) . . . . ? O2 C4 C5 O3 -65.4(3) . . . . ? C5 O3 C6 C7 -169.7(2) . . . . ? C8 O4 C7 C6 -163.1(2) . . . . ? O3 C6 C7 O4 69.1(3) . . . . ? C7 O4 C8 C9 172.24(19) . . . . ? C10 O5 C9 C8 169.0(2) . . . . ? O4 C8 C9 O5 -62.7(3) . . . . ? C9 O5 C10 C11 13.9(3) . . . . ? C9 O5 C10 C1 -165.70(19) . . . . ? C18 C1 C10 C11 0.8(3) . . . . ? O1 C1 C10 C11 -179.4(2) . . . . ? C18 C1 C10 O5 -179.5(2) . . . . ? O1 C1 C10 O5 0.3(3) . . . . ? O5 C10 C11 C12 179.1(2) . . . . ? C1 C10 C11 C12 -1.2(3) . . . . ? C10 C11 C12 C13 -178.3(2) . . . . ? C10 C11 C12 C17 0.6(3) . . . . ? C11 C12 C13 C14 179.0(2) . . . . ? C17 C12 C13 C14 0.2(4) . . . . ? C12 C13 C14 C15 -0.1(4) . . . . ? C13 C14 C15 C16 -0.2(4) . . . . ? C14 C15 C16 C17 0.5(4) . . . . ? C15 C16 C17 C12 -0.3(4) . . . . ? C15 C16 C17 C18 -179.8(2) . . . . ? C13 C12 C17 C16 0.0(3) . . . . ? C11 C12 C17 C16 -178.9(2) . . . . ? C13 C12 C17 C18 179.5(2) . . . . ? C11 C12 C17 C18 0.6(3) . . . . ? O1 C1 C18 C17 -179.4(2) . . . . ? C10 C1 C18 C17 0.4(3) . . . . ? C16 C17 C18 C1 178.4(2) . . . . ? C12 C17 C18 C1 -1.0(3) . . . . ? O6 N4 C19 N1 175.2(2) . . . . ? O6 N4 C19 C20 -1.5(2) . . . . ? O6 N3 C20 N2 -177.0(2) . . . . ? O6 N3 C20 C19 -1.0(2) . . . . ? N4 C19 C20 N3 1.7(3) . . . . ? N1 C19 C20 N3 -174.9(2) . . . . ? N4 C19 C20 N2 177.5(2) . . . . ? N1 C19 C20 N2 1.0(4) . . . . ? 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 H2N2 O1W 0.936(19) 1.91(2) 2.839(3) 173(3) . N1 H2N1 O1W 0.85(2) 2.31(2) 3.131(3) 163(3) . O1W H2W O4 0.86(2) 2.03(2) 2.886(2) 179(3) . O1W H1W O2 0.84(2) 2.07(2) 2.890(2) 168(3) . _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 25.28 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 0.138 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.030