# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Kole, Goutam' 'Tan, Geok' 'Vittal, Jagadese' _publ_contact_author_name 'Vittal, Jagadese' _publ_contact_author_email chmjjv@nus.edu.sg _publ_section_title ; Crystal engineering studies on the salts of trans-4,4'-stilbenedicarboxylic acid in the context of solid state [2+2] cycloaddition ; # Attachment '- Goutam.cif.txt' data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 779310' #data_9152 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H57 N3 O6' _chemical_formula_weight 699.91 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 12.1042(10) _cell_length_b 12.6256(10) _cell_length_c 15.2007(11) _cell_angle_alpha 110.722(2) _cell_angle_beta 111.880(2) _cell_angle_gamma 95.796(2) _cell_volume 1942.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 1573 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 24.72 _exptl_crystal_description 'Thin Plate' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9719 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13954 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0767 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8874 _reflns_number_gt 5245 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1086P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8874 _refine_ls_number_parameters 509 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1291 _refine_ls_R_factor_gt 0.0793 _refine_ls_wR_factor_ref 0.2255 _refine_ls_wR_factor_gt 0.1976 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.051 _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 1.06462(16) -0.35342(16) 0.63056(15) 0.0407(5) Uani 1 1 d . . . O2 O 1.13287(17) -0.27793(16) 0.54232(15) 0.0432(5) Uani 1 1 d . . . O3 O 0.35486(18) 0.41238(16) 0.65327(14) 0.0431(5) Uani 1 1 d . . . O4 O 0.36311(17) 0.44301(17) 0.52033(15) 0.0445(5) Uani 1 1 d . . . O5 O 0.3690(2) 0.62341(19) 0.07154(16) 0.0541(6) Uani 1 1 d . . . O6 O 0.33839(19) 0.61039(17) -0.08564(15) 0.0468(5) Uani 1 1 d . . . N1 N 0.15915(19) 0.51017(19) 0.42251(16) 0.0346(5) Uani 1 1 d . . . H1A H 0.0893 0.4536 0.3965 0.052 Uiso 1 1 calc R . . H1B H 0.1560 0.5772 0.4682 0.052 Uiso 1 1 calc R . . H1C H 0.2246 0.4876 0.4555 0.052 Uiso 1 1 calc R . . N2 N 0.30016(18) 0.62183(18) 0.72505(16) 0.0325(5) Uani 1 1 d . . . H2A H 0.3083 0.6246 0.7872 0.049 Uiso 1 1 calc R . . H2B H 0.3116 0.5538 0.6884 0.049 Uiso 1 1 calc R . . H2C H 0.2239 0.6263 0.6890 0.049 Uiso 1 1 calc R . . N3 N 0.6003(2) 0.59639(19) 0.15729(17) 0.0387(5) Uani 1 1 d . A . H3A H 0.6115 0.5273 0.1225 0.058 Uiso 1 1 calc R . . H3B H 0.5255 0.6016 0.1190 0.058 Uiso 1 1 calc R . . H3C H 0.6051 0.6010 0.2191 0.058 Uiso 1 1 calc R . . C1 C 1.0642(2) -0.2859(2) 0.58507(19) 0.0342(6) Uani 1 1 d . . . C2 C 0.9756(2) -0.2104(2) 0.58449(18) 0.0310(5) Uani 1 1 d . . . C3 C 0.9537(2) -0.1496(2) 0.5220(2) 0.0355(6) Uani 1 1 d . . . H3 H 0.9938 -0.1570 0.4786 0.043 Uiso 1 1 calc R . . C4 C 0.8741(2) -0.0787(2) 0.5226(2) 0.0368(6) Uani 1 1 d . . . H4 H 0.8613 -0.0381 0.4799 0.044 Uiso 1 1 calc R . . C5 C 0.8124(2) -0.0664(2) 0.58540(19) 0.0319(6) Uani 1 1 d . . . C6 C 0.8323(2) -0.1300(2) 0.6463(2) 0.0358(6) Uani 1 1 d . . . H6 H 0.7905 -0.1247 0.6883 0.043 Uiso 1 1 calc R . . C7 C 0.9126(2) -0.2007(2) 0.64554(19) 0.0336(6) Uani 1 1 d . . . H7 H 0.9246 -0.2426 0.6870 0.040 Uiso 1 1 calc R . . C8 C 0.7276(2) 0.0085(2) 0.5899(2) 0.0365(6) Uani 1 1 d . . . H8 H 0.6869 0.0063 0.6315 0.044 Uiso 1 1 calc R . . C9 C 0.7018(2) 0.0789(2) 0.5422(2) 0.0373(6) Uani 1 1 d . . . H9 H 0.7407 0.0808 0.4994 0.045 Uiso 1 1 calc R . . C10 C 0.6177(2) 0.1543(2) 0.55046(19) 0.0324(6) Uani 1 1 d . . . C11 C 0.5855(2) 0.2117(2) 0.4853(2) 0.0393(6) Uani 1 1 d . . . H11 H 0.6149 0.1989 0.4343 0.047 Uiso 1 1 calc R . . C12 C 0.5109(2) 0.2876(2) 0.4940(2) 0.0373(6) Uani 1 1 d . . . H12 H 0.4904 0.3251 0.4489 0.045 Uiso 1 1 calc R . . C13 C 0.4666(2) 0.3083(2) 0.56838(18) 0.0305(5) Uani 1 1 d . . . C14 C 0.4986(3) 0.2512(2) 0.6337(2) 0.0390(6) Uani 1 1 d . . . H14 H 0.4699 0.2647 0.6852 0.047 Uiso 1 1 calc R . . C15 C 0.5715(3) 0.1750(2) 0.6240(2) 0.0395(6) Uani 1 1 d . . . H15 H 0.5904 0.1363 0.6683 0.047 Uiso 1 1 calc R . . C16 C 0.3887(2) 0.3945(2) 0.5808(2) 0.0330(6) Uani 1 1 d . . . C17 C 0.3205(2) 0.6468(2) -0.0049(2) 0.0375(6) Uani 1 1 d . . . C19 C 0.1783(2) 0.7576(2) -0.08073(19) 0.0346(6) Uani 1 1 d . . . H19 H 0.1894 0.7259 -0.1419 0.042 Uiso 1 1 calc R . . C21 C 0.0872(2) 0.8831(2) 0.0168(2) 0.0348(6) Uani 1 1 d . . . C22 C 0.1400(2) 0.8471(2) 0.0962(2) 0.0379(6) Uani 1 1 d . . . H22 H 0.1255 0.8754 0.1559 0.046 Uiso 1 1 calc R . . C23 C 0.2136(2) 0.7703(2) 0.0884(2) 0.0363(6) Uani 1 1 d . . . H23 H 0.2495 0.7483 0.1434 0.044 Uiso 1 1 calc R . . C24 C 0.0187(3) 0.9720(2) 0.0300(2) 0.0406(6) Uani 1 1 d . . . H24 H -0.0009 0.9913 0.0871 0.049 Uiso 1 1 calc R . . C18 C 0.2349(2) 0.7254(2) 0.00034(19) 0.0311(5) Uani 1 1 d . . . C20 C 0.1063(2) 0.8351(2) -0.0731(2) 0.0361(6) Uani 1 1 d . . . H20 H 0.0697 0.8561 -0.1287 0.043 Uiso 1 1 calc R . . C25 C 0.1717(2) 0.5302(2) 0.3353(2) 0.0361(6) Uani 1 1 d . . . H25 H 0.2404 0.6016 0.3668 0.043 Uiso 1 1 calc R . . C30 C 0.2042(3) 0.4294(3) 0.2693(2) 0.0484(7) Uani 1 1 d . . . H30A H 0.1379 0.3570 0.2371 0.058 Uiso 1 1 calc R . . H30B H 0.2804 0.4176 0.3134 0.058 Uiso 1 1 calc R . . C29 C 0.2220(3) 0.4560(3) 0.1837(2) 0.0550(8) Uani 1 1 d . . . H29A H 0.2927 0.5247 0.2162 0.066 Uiso 1 1 calc R . . H29B H 0.2400 0.3890 0.1393 0.066 Uiso 1 1 calc R . . C28 C 0.1078(3) 0.4799(3) 0.1167(2) 0.0575(9) Uani 1 1 d . . . H28A H 0.0394 0.4081 0.0772 0.069 Uiso 1 1 calc R . . H28B H 0.1239 0.5026 0.0663 0.069 Uiso 1 1 calc R . . C27 C 0.0712(4) 0.5772(3) 0.1834(3) 0.0669(10) Uani 1 1 d . . . H27A H -0.0066 0.5861 0.1387 0.080 Uiso 1 1 calc R . . H27B H 0.1347 0.6513 0.2148 0.080 Uiso 1 1 calc R . . C26 C 0.0553(3) 0.5532(3) 0.2704(2) 0.0520(8) Uani 1 1 d . . . H26A H 0.0388 0.6211 0.3150 0.062 Uiso 1 1 calc R . . H26B H -0.0151 0.4848 0.2397 0.062 Uiso 1 1 calc R . . C31 C 0.3943(2) 0.7227(2) 0.7426(2) 0.0356(6) Uani 1 1 d . . . H31 H 0.3808 0.7207 0.6736 0.043 Uiso 1 1 calc R . . C32 C 0.5235(3) 0.7112(3) 0.7947(2) 0.0495(7) Uani 1 1 d . . . H32A H 0.5330 0.6389 0.7491 0.059 Uiso 1 1 calc R . . H32B H 0.5364 0.7063 0.8606 0.059 Uiso 1 1 calc R . . C33 C 0.6193(3) 0.8168(3) 0.8164(3) 0.0675(10) Uani 1 1 d . . . H33A H 0.7022 0.8103 0.8536 0.081 Uiso 1 1 calc R . . H33B H 0.6116 0.8163 0.7498 0.081 Uiso 1 1 calc R . . C34 C 0.6040(3) 0.9323(3) 0.8815(3) 0.0670(10) Uani 1 1 d . . . H34A H 0.6643 0.9979 0.8905 0.080 Uiso 1 1 calc R . . H34B H 0.6199 0.9366 0.9509 0.080 Uiso 1 1 calc R . . C35 C 0.4737(3) 0.9425(3) 0.8280(3) 0.0648(9) Uani 1 1 d . . . H35A H 0.4638 1.0151 0.8729 0.078 Uiso 1 1 calc R . . H35B H 0.4611 0.9467 0.7620 0.078 Uiso 1 1 calc R . . C36 C 0.3773(3) 0.8378(2) 0.8064(2) 0.0491(7) Uani 1 1 d . . . H36A H 0.3840 0.8387 0.8730 0.059 Uiso 1 1 calc R . . H36B H 0.2946 0.8440 0.7683 0.059 Uiso 1 1 calc R . . C37 C 0.6975(3) 0.6942(3) 0.1757(2) 0.0595(9) Uani 1 1 d D . . H37A H 0.7766 0.6847 0.2196 0.071 Uiso 0.658(4) 1 calc PR A 1 H37B H 0.6871 0.7638 0.2254 0.071 Uiso 0.342(4) 1 calc PR A 2 C38 C 0.7064(6) 0.6844(6) 0.0757(4) 0.0606(19) Uani 0.658(4) 1 d PD A 1 H38A H 0.6287 0.6890 0.0270 0.073 Uiso 0.658(4) 1 calc PR A 1 H38B H 0.7199 0.6082 0.0420 0.073 Uiso 0.658(4) 1 calc PR A 1 C39 C 0.8144(9) 0.7846(4) 0.1011(8) 0.086(3) Uani 0.658(4) 1 d PD A 1 H39A H 0.8929 0.7755 0.1446 0.103 Uiso 0.658(4) 1 calc PR A 1 H39B H 0.8166 0.7794 0.0359 0.103 Uiso 0.658(4) 1 calc PR A 1 C40 C 0.7993(7) 0.9051(4) 0.1589(4) 0.0723(19) Uani 0.658(4) 1 d PD A 1 H40A H 0.8676 0.9675 0.1734 0.087 Uiso 0.658(4) 1 calc PR A 1 H40B H 0.7217 0.9153 0.1151 0.087 Uiso 0.658(4) 1 calc PR A 1 C41 C 0.7987(5) 0.9133(4) 0.2611(4) 0.0664(16) Uani 0.658(4) 1 d PD A 1 H41A H 0.7885 0.9900 0.2982 0.080 Uiso 0.658(4) 1 calc PR A 1 H41B H 0.8778 0.9064 0.3058 0.080 Uiso 0.658(4) 1 calc PR A 1 C42 C 0.6925(4) 0.8147(3) 0.2387(4) 0.0517(13) Uani 0.658(4) 1 d PD A 1 H42A H 0.6961 0.8186 0.3053 0.062 Uiso 0.658(4) 1 calc PR A 1 H42B H 0.6134 0.8274 0.2005 0.062 Uiso 0.658(4) 1 calc PR A 1 C38X C 0.6532(13) 0.7131(13) 0.0750(7) 0.096(6) Uani 0.342(4) 1 d PD A 2 H38C H 0.5692 0.7228 0.0537 0.115 Uiso 0.342(4) 1 calc PR A 2 H38D H 0.6555 0.6476 0.0174 0.115 Uiso 0.342(4) 1 calc PR A 2 C39X C 0.7491(8) 0.8283(17) 0.1091(16) 0.111(7) Uani 0.342(4) 1 d PD A 2 H39C H 0.7373 0.8416 0.0469 0.133 Uiso 0.342(4) 1 calc PR A 2 H39D H 0.7323 0.8939 0.1560 0.133 Uiso 0.342(4) 1 calc PR A 2 C40X C 0.8856(8) 0.8297(17) 0.1649(11) 0.118(8) Uani 0.342(4) 1 d PD A 2 H40C H 0.9057 0.7673 0.1180 0.141 Uiso 0.342(4) 1 calc PR A 2 H40D H 0.9400 0.9053 0.1845 0.141 Uiso 0.342(4) 1 calc PR A 2 C41X C 0.9046(10) 0.8105(9) 0.2633(8) 0.085(4) Uani 0.342(4) 1 d PD A 2 H41C H 0.8841 0.8734 0.3095 0.102 Uiso 0.342(4) 1 calc PR A 2 H41D H 0.9919 0.8151 0.3011 0.102 Uiso 0.342(4) 1 calc PR A 2 C42X C 0.8248(5) 0.6911(8) 0.2374(8) 0.065(3) Uani 0.342(4) 1 d PD A 2 H42C H 0.8477 0.6260 0.1959 0.078 Uiso 0.342(4) 1 calc PR A 2 H42D H 0.8325 0.6835 0.3013 0.078 Uiso 0.342(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 O1 0.0394(10) 0.0394(11) 0.0537(12) 0.0288(9) 0.0205(9) 0.0187(9) O2 0.0449(11) 0.0444(11) 0.0563(12) 0.0258(10) 0.0314(10) 0.0238(9) O3 0.0573(12) 0.0447(11) 0.0441(11) 0.0239(9) 0.0298(10) 0.0322(10) O4 0.0485(11) 0.0531(12) 0.0509(12) 0.0351(10) 0.0242(10) 0.0315(10) O5 0.0653(13) 0.0714(15) 0.0470(12) 0.0368(11) 0.0290(11) 0.0435(12) O6 0.0679(14) 0.0494(12) 0.0455(12) 0.0270(10) 0.0355(11) 0.0366(11) N1 0.0352(11) 0.0382(12) 0.0334(12) 0.0182(10) 0.0139(10) 0.0152(10) N2 0.0339(11) 0.0329(11) 0.0356(12) 0.0164(9) 0.0166(9) 0.0153(9) N3 0.0488(13) 0.0373(13) 0.0408(13) 0.0229(10) 0.0226(11) 0.0196(11) C1 0.0314(13) 0.0323(14) 0.0328(14) 0.0103(11) 0.0110(11) 0.0097(11) C2 0.0313(13) 0.0249(12) 0.0319(13) 0.0106(10) 0.0102(11) 0.0080(10) C3 0.0418(14) 0.0376(15) 0.0388(14) 0.0197(12) 0.0248(12) 0.0162(12) C4 0.0394(14) 0.0389(15) 0.0398(15) 0.0233(12) 0.0173(12) 0.0164(12) C5 0.0309(13) 0.0269(13) 0.0350(14) 0.0109(11) 0.0131(11) 0.0101(11) C6 0.0424(14) 0.0361(14) 0.0403(15) 0.0183(12) 0.0260(12) 0.0176(12) C7 0.0399(14) 0.0327(14) 0.0349(14) 0.0178(11) 0.0186(12) 0.0141(12) C8 0.0386(14) 0.0331(14) 0.0405(15) 0.0145(12) 0.0199(12) 0.0141(12) C9 0.0375(14) 0.0380(15) 0.0408(15) 0.0162(12) 0.0198(12) 0.0191(12) C10 0.0339(13) 0.0298(13) 0.0338(14) 0.0131(11) 0.0141(11) 0.0138(11) C11 0.0442(15) 0.0437(16) 0.0423(15) 0.0222(13) 0.0255(13) 0.0208(13) C12 0.0433(15) 0.0409(15) 0.0353(14) 0.0219(12) 0.0175(12) 0.0197(13) C13 0.0288(12) 0.0264(13) 0.0315(13) 0.0116(10) 0.0088(10) 0.0088(10) C14 0.0487(16) 0.0403(15) 0.0415(15) 0.0214(13) 0.0266(13) 0.0236(13) C15 0.0512(16) 0.0394(15) 0.0391(15) 0.0234(13) 0.0213(13) 0.0250(13) C16 0.0318(13) 0.0315(13) 0.0343(14) 0.0136(11) 0.0118(11) 0.0144(11) C17 0.0409(15) 0.0367(15) 0.0407(16) 0.0190(12) 0.0200(13) 0.0162(12) C19 0.0387(14) 0.0365(14) 0.0307(13) 0.0137(11) 0.0169(11) 0.0136(12) C21 0.0346(13) 0.0348(14) 0.0398(15) 0.0171(12) 0.0193(12) 0.0122(12) C22 0.0482(16) 0.0409(15) 0.0370(15) 0.0186(12) 0.0271(13) 0.0207(13) C23 0.0431(15) 0.0367(15) 0.0358(14) 0.0195(12) 0.0192(12) 0.0143(12) C24 0.0474(16) 0.0412(16) 0.0453(16) 0.0196(12) 0.0290(14) 0.0213(13) C18 0.0337(13) 0.0265(13) 0.0332(13) 0.0122(11) 0.0151(11) 0.0082(11) C20 0.0385(14) 0.0386(15) 0.0357(14) 0.0185(12) 0.0169(12) 0.0162(12) C25 0.0383(14) 0.0380(15) 0.0338(14) 0.0189(12) 0.0149(12) 0.0076(12) C30 0.0577(18) 0.0593(19) 0.0449(17) 0.0297(15) 0.0296(15) 0.0263(16) C29 0.0546(19) 0.069(2) 0.0415(17) 0.0209(16) 0.0252(15) 0.0107(17) C28 0.060(2) 0.065(2) 0.0385(17) 0.0253(16) 0.0141(15) 0.0016(17) C27 0.088(3) 0.077(2) 0.053(2) 0.045(2) 0.0281(19) 0.032(2) C26 0.0550(18) 0.065(2) 0.0466(18) 0.0331(16) 0.0213(15) 0.0300(17) C31 0.0357(14) 0.0407(15) 0.0330(14) 0.0197(12) 0.0143(11) 0.0082(12) C32 0.0377(15) 0.0519(19) 0.0567(19) 0.0238(15) 0.0177(14) 0.0126(14) C33 0.0411(18) 0.082(3) 0.070(2) 0.030(2) 0.0213(17) -0.0011(18) C34 0.054(2) 0.061(2) 0.063(2) 0.0210(19) 0.0135(17) -0.0083(17) C35 0.068(2) 0.0369(18) 0.072(2) 0.0191(17) 0.0202(19) 0.0034(16) C36 0.0463(16) 0.0333(15) 0.0569(19) 0.0159(14) 0.0156(15) 0.0076(13) C37 0.076(2) 0.0476(19) 0.066(2) 0.0339(17) 0.0348(19) 0.0118(17) C38 0.089(5) 0.049(3) 0.053(3) 0.022(3) 0.043(3) 0.007(3) C39 0.098(6) 0.075(5) 0.119(7) 0.041(5) 0.086(6) 0.006(5) C40 0.097(5) 0.046(3) 0.078(4) 0.022(3) 0.052(4) -0.003(3) C41 0.081(4) 0.044(3) 0.060(3) 0.013(2) 0.032(3) -0.008(3) C42 0.061(3) 0.039(3) 0.059(3) 0.019(2) 0.034(3) 0.007(2) C38X 0.086(11) 0.117(15) 0.072(9) 0.045(10) 0.022(8) 0.007(9) C39X 0.054(8) 0.153(17) 0.148(16) 0.136(15) 0.009(9) -0.011(9) C40X 0.027(6) 0.179(18) 0.143(14) 0.119(14) -0.002(7) -0.025(8) C41X 0.061(7) 0.102(10) 0.098(9) 0.055(8) 0.033(7) 0.005(7) C42X 0.065(7) 0.057(6) 0.076(7) 0.037(6) 0.027(6) 0.007(5) _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 1.273(3) . ? O2 C1 1.247(3) . ? O3 C16 1.270(3) . ? O4 C16 1.241(3) . ? O5 C17 1.246(3) . ? O6 C17 1.258(3) . ? N1 C25 1.491(3) . ? N2 C31 1.494(3) . ? N3 C37 1.484(4) . ? C1 C2 1.504(3) . ? C2 C7 1.387(3) . ? C2 C3 1.389(3) . ? C3 C4 1.381(3) . ? C4 C5 1.394(3) . ? C5 C6 1.400(3) . ? C5 C8 1.468(3) . ? C6 C7 1.385(3) . ? C8 C9 1.325(3) . ? C9 C10 1.471(3) . ? C10 C15 1.385(3) . ? C10 C11 1.392(3) . ? C11 C12 1.386(3) . ? C12 C13 1.380(3) . ? C13 C14 1.390(3) . ? C13 C16 1.517(3) . ? C14 C15 1.376(3) . ? C17 C18 1.509(3) . ? C19 C20 1.377(3) . ? C19 C18 1.391(3) . ? C21 C22 1.394(3) . ? C21 C20 1.402(3) . ? C21 C24 1.463(3) . ? C22 C23 1.385(3) . ? C23 C18 1.390(3) . ? C24 C24 1.324(5) 2_575 ? C25 C30 1.508(4) . ? C25 C26 1.514(4) . ? C30 C29 1.536(4) . ? C29 C28 1.514(4) . ? C28 C27 1.515(5) . ? C27 C26 1.528(4) . ? C31 C32 1.515(4) . ? C31 C36 1.520(4) . ? C32 C33 1.524(4) . ? C33 C34 1.519(5) . ? C34 C35 1.525(5) . ? C35 C36 1.520(4) . ? C37 C42X 1.489(5) . ? C37 C42 1.505(4) . ? C37 C38 1.527(4) . ? C37 C38X 1.537(5) . ? C38 C39 1.550(4) . ? C39 C40 1.534(5) . ? C40 C41 1.523(4) . ? C41 C42 1.540(4) . ? C38X C39X 1.552(5) . ? C39X C40X 1.545(5) . ? C40X C41X 1.536(5) . ? C41X C42X 1.537(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 124.2(2) . . ? O2 C1 C2 118.5(2) . . ? O1 C1 C2 117.3(2) . . ? C7 C2 C3 118.2(2) . . ? C7 C2 C1 120.8(2) . . ? C3 C2 C1 121.0(2) . . ? C4 C3 C2 121.2(2) . . ? C3 C4 C5 121.0(2) . . ? C4 C5 C6 117.7(2) . . ? C4 C5 C8 123.4(2) . . ? C6 C5 C8 118.8(2) . . ? C7 C6 C5 120.9(2) . . ? C6 C7 C2 121.0(2) . . ? C9 C8 C5 127.5(2) . . ? C8 C9 C10 125.7(2) . . ? C15 C10 C11 117.4(2) . . ? C15 C10 C9 122.7(2) . . ? C11 C10 C9 119.9(2) . . ? C12 C11 C10 121.5(2) . . ? C13 C12 C11 120.5(2) . . ? C12 C13 C14 118.2(2) . . ? C12 C13 C16 120.7(2) . . ? C14 C13 C16 121.0(2) . . ? C15 C14 C13 121.1(2) . . ? C14 C15 C10 121.3(2) . . ? O4 C16 O3 124.5(2) . . ? O4 C16 C13 118.2(2) . . ? O3 C16 C13 117.3(2) . . ? O5 C17 O6 124.8(2) . . ? O5 C17 C18 117.4(2) . . ? O6 C17 C18 117.8(2) . . ? C20 C19 C18 121.3(2) . . ? C22 C21 C20 118.0(2) . . ? C22 C21 C24 120.3(2) . . ? C20 C21 C24 121.7(2) . . ? C23 C22 C21 121.0(2) . . ? C22 C23 C18 120.8(2) . . ? C24 C24 C21 126.7(3) 2_575 . ? C23 C18 C19 118.2(2) . . ? C23 C18 C17 120.4(2) . . ? C19 C18 C17 121.3(2) . . ? C19 C20 C21 120.6(2) . . ? N1 C25 C30 111.4(2) . . ? N1 C25 C26 110.3(2) . . ? C30 C25 C26 111.8(2) . . ? C25 C30 C29 109.7(2) . . ? C28 C29 C30 111.2(3) . . ? C29 C28 C27 111.0(3) . . ? C28 C27 C26 112.6(3) . . ? C25 C26 C27 109.7(3) . . ? N2 C31 C32 110.4(2) . . ? N2 C31 C36 109.8(2) . . ? C32 C31 C36 111.9(2) . . ? C31 C32 C33 110.2(2) . . ? C34 C33 C32 112.1(3) . . ? C33 C34 C35 110.5(3) . . ? C36 C35 C34 111.0(3) . . ? C31 C36 C35 111.2(3) . . ? N3 C37 C42X 113.0(4) . . ? N3 C37 C42 114.4(3) . . ? C42X C37 C42 103.2(5) . . ? N3 C37 C38 112.9(3) . . ? C42X C37 C38 99.6(5) . . ? C42 C37 C38 112.5(3) . . ? N3 C37 C38X 106.4(5) . . ? C42X C37 C38X 126.0(7) . . ? C42 C37 C38X 92.1(7) . . ? C38 C37 C38X 29.1(6) . . ? C37 C38 C39 110.4(4) . . ? C40 C39 C38 110.8(6) . . ? C41 C40 C39 109.1(5) . . ? C40 C41 C42 110.1(4) . . ? C37 C42 C41 112.8(3) . . ? C37 C38X C39X 101.9(7) . . ? C40X C39X C38X 115.0(12) . . ? C41X C40X C39X 108.6(10) . . ? C40X C41X C42X 112.5(9) . . ? C37 C42X C41X 102.9(6) . . ? 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 O1 0.90 1.96 2.840(3) 166.8 2_656 N1 H1B O2 0.90 1.89 2.781(3) 169.6 1_465 N1 H1C O4 0.90 1.86 2.757(3) 177.4 . N2 H2A O6 0.90 1.91 2.798(3) 170.6 1_556 N2 H2B O3 0.90 1.86 2.733(3) 162.1 . N2 H2C O1 0.90 1.89 2.781(3) 172.6 1_465 N3 H3A O6 0.90 1.87 2.745(3) 165.0 2_665 N3 H3B O5 0.90 1.85 2.729(3) 165.8 . N3 H3C O3 0.90 1.89 2.770(3) 165.1 2_666 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.644 _refine_diff_density_min -0.514 _refine_diff_density_rms 0.052 #===END data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 779311' #data_8666b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 N2 O4' _chemical_formula_weight 328.36 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.156(2) _cell_length_b 9.334(2) _cell_length_c 8.385(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.400(5) _cell_angle_gamma 90.00 _cell_volume 792.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 492 _cell_measurement_theta_min 3.27 _cell_measurement_theta_max 24.23 _exptl_crystal_description 'Thin Plate' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9712 _exptl_absorpt_correction_T_max 0.9941 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4309 _diffrn_reflns_av_R_equivalents 0.0701 _diffrn_reflns_av_sigmaI/netI 0.0849 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1812 _reflns_number_gt 1265 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+0.5660P] 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 1812 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1244 _refine_ls_R_factor_gt 0.0795 _refine_ls_wR_factor_ref 0.1674 _refine_ls_wR_factor_gt 0.1516 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 0.6501(2) 0.5799(2) 1.1825(2) 0.0173(5) Uani 1 1 d . . . O2 O 0.6325(2) 0.3468(2) 1.1292(2) 0.0161(5) Uani 1 1 d . . . C1 C 0.9727(3) 0.5503(3) 0.5442(3) 0.0169(7) Uani 1 1 d . . . H1 H 0.9838 0.6472 0.5131 0.020 Uiso 1 1 calc R . . C2 C 0.8975(3) 0.5253(3) 0.6846(3) 0.0144(6) Uani 1 1 d . . . C3 C 0.8721(3) 0.3887(3) 0.7451(3) 0.0150(7) Uani 1 1 d . . . H3 H 0.9048 0.3064 0.6944 0.018 Uiso 1 1 calc R . . C4 C 0.8003(3) 0.3718(3) 0.8773(3) 0.0141(6) Uani 1 1 d . . . H4 H 0.7841 0.2782 0.9158 0.017 Uiso 1 1 calc R . . C5 C 0.7509(3) 0.4907(3) 0.9554(3) 0.0134(6) Uani 1 1 d . . . C6 C 0.7752(3) 0.6268(3) 0.8957(3) 0.0145(6) Uani 1 1 d . . . H6 H 0.7422 0.7088 0.9466 0.017 Uiso 1 1 calc R . . C7 C 0.8469(3) 0.6439(3) 0.7632(3) 0.0144(6) Uani 1 1 d . . . H7 H 0.8622 0.7376 0.7245 0.017 Uiso 1 1 calc R . . C8 C 0.6714(3) 0.4729(3) 1.0996(3) 0.0123(6) Uani 1 1 d . . . C9 C 0.4453(3) 0.0423(3) 0.9569(3) 0.0135(6) Uani 1 1 d . . . H9A H 0.4051 -0.0143 0.8659 0.016 Uiso 1 1 calc R . . H9B H 0.3759 0.0628 1.0305 0.016 Uiso 1 1 calc R . . N1 N 0.4982(3) 0.1785(3) 0.8975(3) 0.0118(5) Uani 1 1 d . . . H1N H 0.551(3) 0.232(3) 0.976(4) 0.014 Uiso 1 1 d . . . H2N H 0.555(3) 0.164(3) 0.805(4) 0.014 Uiso 1 1 d . . . H3N H 0.430(3) 0.242(3) 0.864(4) 0.014 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 0.0264(13) 0.0157(11) 0.0102(10) -0.0018(9) 0.0042(9) 0.0028(9) O2 0.0278(12) 0.0133(11) 0.0081(10) 0.0002(8) 0.0062(8) -0.0007(9) C1 0.0241(17) 0.0142(15) 0.0127(14) 0.0050(12) 0.0020(12) -0.0021(13) C2 0.0162(16) 0.0195(15) 0.0074(14) -0.0006(12) -0.0005(12) 0.0013(12) C3 0.0196(16) 0.0115(15) 0.0141(15) -0.0006(12) 0.0018(12) 0.0043(12) C4 0.0165(15) 0.0137(14) 0.0123(14) 0.0005(12) 0.0021(12) 0.0005(12) C5 0.0134(15) 0.0169(15) 0.0098(14) 0.0001(12) 0.0005(11) 0.0009(11) C6 0.0189(16) 0.0132(15) 0.0114(14) -0.0011(12) 0.0017(12) 0.0016(12) C7 0.0177(16) 0.0128(14) 0.0127(14) 0.0022(12) 0.0018(12) -0.0003(12) C8 0.0172(16) 0.0124(14) 0.0069(14) 0.0022(11) -0.0018(11) 0.0038(11) C9 0.0204(17) 0.0126(14) 0.0078(13) -0.0009(11) 0.0023(12) -0.0032(12) N1 0.0164(14) 0.0102(12) 0.0092(12) 0.0002(10) 0.0033(10) 0.0009(10) _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 C8 1.245(3) . ? O2 C8 1.272(3) . ? C1 C1 1.343(6) 3_766 ? C1 C2 1.470(4) . ? C2 C3 1.404(4) . ? C2 C7 1.406(4) . ? C3 C4 1.382(4) . ? C4 C5 1.401(4) . ? C5 C6 1.395(4) . ? C5 C8 1.513(4) . ? C6 C7 1.383(4) . ? C9 N1 1.482(3) . ? C9 C9 1.502(6) 3_657 ? 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 C1 C2 126.4(3) 3_766 . ? C3 C2 C7 117.5(3) . . ? C3 C2 C1 123.7(3) . . ? C7 C2 C1 118.8(3) . . ? C4 C3 C2 121.1(3) . . ? C3 C4 C5 121.0(3) . . ? C6 C5 C4 118.3(3) . . ? C6 C5 C8 120.5(3) . . ? C4 C5 C8 121.2(3) . . ? C7 C6 C5 120.8(3) . . ? C6 C7 C2 121.3(3) . . ? O1 C8 O2 124.3(3) . . ? O1 C8 C5 119.0(3) . . ? O2 C8 C5 116.7(2) . . ? N1 C9 C9 109.8(3) . 3_657 ? 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 H3N O1 0.94(3) 1.88(3) 2.766(3) 157(3) 3_667 N1 H2N O2 1.01(3) 1.73(3) 2.729(3) 171(3) 4_565 N1 H1N O2 0.96(3) 1.82(3) 2.774(3) 173(3) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.349 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.074 #===END data_compound_4 _database_code_depnum_ccdc_archive 'CCDC 779312' #data_8570 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H28 N2 O6' _chemical_formula_weight 392.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 7.4542(13) _cell_length_b 9.7070(16) _cell_length_c 13.610(2) _cell_angle_alpha 100.688(2) _cell_angle_beta 96.117(3) _cell_angle_gamma 90.070(3) _cell_volume 962.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3326 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 27.24 _exptl_crystal_description PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9278 _exptl_absorpt_correction_T_max 0.9910 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12348 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4407 _reflns_number_gt 3637 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0916P)^2^+0.5227P] 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 4407 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.1790 _refine_ls_wR_factor_gt 0.1722 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 N1 N 0.4448(2) 0.72566(18) 0.33975(13) 0.0235(4) Uani 1 1 d . . . H1A H 0.3776 0.6460 0.3267 0.035 Uiso 1 1 calc R . . H1B H 0.5521 0.7088 0.3157 0.035 Uiso 1 1 calc R . . H1C H 0.3871 0.7910 0.3100 0.035 Uiso 1 1 calc R . . N2 N 0.0094(2) 0.77257(18) 0.63126(12) 0.0210(4) Uani 1 1 d . . . H2A H 0.0659 0.7039 0.6578 0.031 Uiso 1 1 calc R . . H2B H -0.0996 0.7857 0.6539 0.031 Uiso 1 1 calc R . . H2C H 0.0757 0.8525 0.6496 0.031 Uiso 1 1 calc R . . O1 O -0.1758(2) 0.45721(15) 0.29814(12) 0.0266(4) Uani 1 1 d . . . O2 O -0.2328(2) 0.67188(15) 0.27037(12) 0.0280(4) Uani 1 1 d . . . O3 O 0.6855(2) 0.81494(15) 0.70723(12) 0.0289(4) Uani 1 1 d . . . O4 O 0.7235(2) 1.04505(15) 0.72417(12) 0.0290(4) Uani 1 1 d . . . C1 C -0.1460(2) 0.5605(2) 0.25844(14) 0.0172(4) Uani 1 1 d . . . C2 C 0.0043(2) 0.55301(19) 0.19211(13) 0.0163(4) Uani 1 1 d . . . C3 C 0.1316(3) 0.4479(2) 0.18960(14) 0.0184(4) Uani 1 1 d . . . H3 H 0.1227 0.3793 0.2295 0.022 Uiso 1 1 calc R . . C4 C 0.2708(3) 0.4424(2) 0.12965(14) 0.0195(4) Uani 1 1 d . . . H4 H 0.3575 0.3724 0.1310 0.023 Uiso 1 1 calc R . . C5 C 0.2840(2) 0.5401(2) 0.06695(14) 0.0174(4) Uani 1 1 d . . . C6 C 0.1544(3) 0.6437(2) 0.06900(15) 0.0212(4) Uani 1 1 d . . . H6 H 0.1594 0.7099 0.0269 0.025 Uiso 1 1 calc R . . C7 C 0.0188(3) 0.6513(2) 0.13148(15) 0.0202(4) Uani 1 1 d . . . H7 H -0.0645 0.7241 0.1328 0.024 Uiso 1 1 calc R . . C8 C 0.4263(3) 0.5386(2) 0.00024(15) 0.0202(4) Uani 1 1 d . . . H8 H 0.4120 0.5983 -0.0470 0.024 Uiso 1 1 calc R . . C9 C 0.6460(3) 0.9392(2) 0.74156(14) 0.0183(4) Uani 1 1 d . . . C10 C 0.4958(2) 0.9619(2) 0.80827(14) 0.0162(4) Uani 1 1 d . . . C11 C 0.4772(3) 1.0920(2) 0.86866(15) 0.0206(4) Uani 1 1 d . . . H11 H 0.5573 1.1661 0.8668 0.025 Uiso 1 1 calc R . . C12 C 0.3417(3) 1.1135(2) 0.93152(15) 0.0216(4) Uani 1 1 d . . . H12 H 0.3339 1.2014 0.9735 0.026 Uiso 1 1 calc R . . C13 C 0.2168(3) 1.0079(2) 0.93406(14) 0.0178(4) Uani 1 1 d . . . C14 C 0.2350(3) 0.8774(2) 0.87263(14) 0.0194(4) Uani 1 1 d . . . H14 H 0.1519 0.8044 0.8724 0.023 Uiso 1 1 calc R . . C15 C 0.3742(3) 0.8546(2) 0.81206(14) 0.0178(4) Uani 1 1 d . . . H15 H 0.3867 0.7653 0.7730 0.021 Uiso 1 1 calc R . . C16 C 0.0743(3) 1.0386(2) 1.00075(15) 0.0210(4) Uani 1 1 d . . . H16 H 0.0893 1.1211 1.0496 0.025 Uiso 1 1 calc R . . C17 C 0.4740(3) 0.7770(2) 0.45013(17) 0.0275(5) Uani 1 1 d . . . H17A H 0.5557 0.8591 0.4644 0.033 Uiso 1 1 calc R . . H17B H 0.5318 0.7038 0.4825 0.033 Uiso 1 1 calc R . . C18 C 0.2983(3) 0.8165(2) 0.49458(16) 0.0247(5) Uani 1 1 d . . . H18A H 0.3248 0.8517 0.5670 0.030 Uiso 1 1 calc R . . H18B H 0.2434 0.8925 0.4642 0.030 Uiso 1 1 calc R . . C19 C 0.1638(3) 0.6944(2) 0.47800(15) 0.0233(4) Uani 1 1 d . . . H19A H 0.1399 0.6579 0.4056 0.028 Uiso 1 1 calc R . . H19B H 0.2181 0.6193 0.5096 0.028 Uiso 1 1 calc R . . C20 C -0.0138(3) 0.7323(2) 0.51974(16) 0.0258(5) Uani 1 1 d . . . H20A H -0.0661 0.8105 0.4909 0.031 Uiso 1 1 calc R . . H20B H -0.0981 0.6520 0.4997 0.031 Uiso 1 1 calc R . . O1W O 0.5202(2) 0.55257(17) 0.63501(12) 0.0295(4) Uani 1 1 d . . . H1WA H 0.411(5) 0.559(4) 0.657(3) 0.069(11) Uiso 1 1 d . . . H1WB H 0.565(5) 0.647(4) 0.663(2) 0.062(10) Uiso 1 1 d . . . O2W O -0.0679(2) 0.94004(17) 0.33148(13) 0.0310(4) Uani 1 1 d . . . H2WA H 0.045(5) 0.933(4) 0.308(3) 0.071(11) Uiso 1 1 d . . . H2WB H -0.121(4) 0.859(3) 0.304(2) 0.043(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0216(9) 0.0203(9) 0.0320(9) 0.0058(7) 0.0161(7) 0.0047(7) N2 0.0181(8) 0.0210(8) 0.0262(9) 0.0056(7) 0.0113(7) 0.0018(7) O1 0.0246(8) 0.0231(8) 0.0373(9) 0.0118(6) 0.0167(6) 0.0038(6) O2 0.0227(8) 0.0192(7) 0.0466(10) 0.0073(6) 0.0215(7) 0.0053(6) O3 0.0246(8) 0.0195(7) 0.0447(9) 0.0016(6) 0.0217(7) 0.0027(6) O4 0.0239(8) 0.0216(8) 0.0477(10) 0.0129(7) 0.0203(7) 0.0043(6) C1 0.0128(9) 0.0168(9) 0.0219(9) 0.0010(7) 0.0063(7) -0.0012(7) C2 0.0137(9) 0.0177(9) 0.0168(9) -0.0006(7) 0.0059(7) -0.0009(7) C3 0.0193(9) 0.0170(9) 0.0210(9) 0.0057(7) 0.0082(7) 0.0023(7) C4 0.0176(9) 0.0191(9) 0.0231(10) 0.0033(7) 0.0087(7) 0.0054(7) C5 0.0141(9) 0.0194(9) 0.0188(9) 0.0013(7) 0.0068(7) -0.0015(7) C6 0.0207(10) 0.0221(10) 0.0244(10) 0.0099(8) 0.0089(8) 0.0035(8) C7 0.0171(9) 0.0189(9) 0.0268(10) 0.0067(8) 0.0080(8) 0.0048(7) C8 0.0201(10) 0.0216(10) 0.0208(9) 0.0045(7) 0.0096(8) -0.0003(8) C9 0.0151(9) 0.0187(9) 0.0228(10) 0.0055(7) 0.0069(7) 0.0025(7) C10 0.0124(9) 0.0196(9) 0.0183(9) 0.0051(7) 0.0061(7) 0.0040(7) C11 0.0175(9) 0.0170(9) 0.0279(10) 0.0030(8) 0.0077(8) -0.0025(7) C12 0.0206(10) 0.0163(9) 0.0264(10) -0.0031(8) 0.0079(8) 0.0010(8) C13 0.0163(9) 0.0194(9) 0.0187(9) 0.0040(7) 0.0063(7) 0.0036(7) C14 0.0172(9) 0.0189(9) 0.0234(10) 0.0044(7) 0.0075(7) -0.0011(7) C15 0.0176(9) 0.0159(9) 0.0199(9) 0.0010(7) 0.0064(7) 0.0014(7) C16 0.0216(10) 0.0197(10) 0.0216(10) 0.0005(7) 0.0089(8) 0.0036(8) C17 0.0176(10) 0.0299(11) 0.0351(12) 0.0025(9) 0.0098(8) -0.0001(8) C18 0.0199(10) 0.0283(11) 0.0255(10) 0.0002(8) 0.0097(8) 0.0012(8) C19 0.0198(10) 0.0274(11) 0.0224(10) -0.0001(8) 0.0095(8) 0.0012(8) C20 0.0163(10) 0.0349(12) 0.0266(11) 0.0045(9) 0.0069(8) -0.0009(8) O1W 0.0276(9) 0.0248(8) 0.0357(9) 0.0005(7) 0.0106(7) 0.0016(7) O2W 0.0268(9) 0.0225(8) 0.0446(10) 0.0024(7) 0.0144(7) 0.0009(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C17 1.485(3) . ? N2 C20 1.487(3) . ? O1 C1 1.254(2) . ? O2 C1 1.254(2) . ? O3 C9 1.258(2) . ? O4 C9 1.250(2) . ? C1 C2 1.506(2) . ? C2 C7 1.383(3) . ? C2 C3 1.393(3) . ? C3 C4 1.382(3) . ? C4 C5 1.398(3) . ? C5 C6 1.394(3) . ? C5 C8 1.466(2) . ? C6 C7 1.382(3) . ? C8 C8 1.330(4) 2_665 ? C9 C10 1.506(2) . ? C10 C11 1.389(3) . ? C10 C15 1.392(3) . ? C11 C12 1.383(3) . ? C12 C13 1.392(3) . ? C13 C14 1.398(3) . ? C13 C16 1.465(3) . ? C14 C15 1.386(3) . ? C16 C16 1.333(4) 2_577 ? C17 C18 1.520(3) . ? C18 C19 1.520(3) . ? C19 C20 1.515(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 O2 C1 O1 124.47(17) . . ? O2 C1 C2 116.77(17) . . ? O1 C1 C2 118.76(17) . . ? C7 C2 C3 118.19(17) . . ? C7 C2 C1 120.35(17) . . ? C3 C2 C1 121.46(17) . . ? C4 C3 C2 121.28(17) . . ? C3 C4 C5 120.68(18) . . ? C6 C5 C4 117.55(17) . . ? C6 C5 C8 119.05(17) . . ? C4 C5 C8 123.40(18) . . ? C7 C6 C5 121.54(18) . . ? C6 C7 C2 120.72(18) . . ? C8 C8 C5 126.6(2) 2_665 . ? O4 C9 O3 124.27(17) . . ? O4 C9 C10 117.93(17) . . ? O3 C9 C10 117.80(17) . . ? C11 C10 C15 118.41(17) . . ? C11 C10 C9 120.01(17) . . ? C15 C10 C9 121.57(16) . . ? C12 C11 C10 120.56(18) . . ? C11 C12 C13 121.49(17) . . ? C12 C13 C14 117.79(17) . . ? C12 C13 C16 118.72(17) . . ? C14 C13 C16 123.48(18) . . ? C15 C14 C13 120.70(18) . . ? C14 C15 C10 121.00(17) . . ? C16 C16 C13 126.7(2) 2_577 . ? N1 C17 C18 112.09(18) . . ? C19 C18 C17 113.02(17) . . ? C20 C19 C18 113.85(17) . . ? N2 C20 C19 111.83(17) . . ? 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 O1W 0.90 2.20 2.794(2) 122.6 2_666 N1 H1B O2 0.90 1.79 2.691(2) 178.3 1_655 N1 H1C O4 0.90 1.90 2.789(2) 167.3 2_676 N2 H2A O1 0.90 1.93 2.826(2) 173.8 2_566 N2 H2B O3 0.90 1.83 2.728(2) 176.8 1_455 N2 H2C O2W 0.90 1.98 2.767(2) 144.5 2_576 O1W H1WA O1 0.90(4) 1.93(4) 2.820(2) 172(3) 2_566 O1W H1WB O3 0.97(4) 1.83(4) 2.789(2) 170(3) . O2W H2WA O4 0.93(4) 1.85(4) 2.764(2) 168(3) 2_676 O2W H2WB O2 0.88(3) 1.95(3) 2.819(2) 168(3) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.474 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.074 #===END data_compound_5 _database_code_depnum_ccdc_archive 'CCDC 779313' #data_8667 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 N2 O4 S2' _chemical_formula_weight 420.53 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 8.9392(4) _cell_length_b 10.5683(5) _cell_length_c 12.3610(6) _cell_angle_alpha 71.1670(10) _cell_angle_beta 75.9040(10) _cell_angle_gamma 67.6480(10) _cell_volume 1012.43(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9652 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.49 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 1.20 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.292 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7208 _exptl_absorpt_correction_T_max 0.9175 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13335 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4634 _reflns_number_gt 4425 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+0.4431P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4634 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0877 _refine_ls_wR_factor_gt 0.0866 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.76747(3) 0.20419(3) 0.85970(2) 0.01595(9) Uani 1 1 d . . . S2 S 0.54610(3) 0.25206(3) 0.95960(2) 0.01505(9) Uani 1 1 d . . . N1 N 0.92153(12) -0.12428(10) 0.98051(9) 0.0160(2) Uani 1 1 d . . . H1A H 1.0051 -0.1011 0.9292 0.024 Uiso 1 1 calc R . . H1B H 0.9524 -0.2198 1.0105 0.024 Uiso 1 1 calc R . . H1C H 0.8958 -0.0808 1.0384 0.024 Uiso 1 1 calc R . . N2 N 0.43248(12) 0.59146(10) 0.85708(8) 0.01419(19) Uani 1 1 d . . . H2A H 0.3574 0.5792 0.9207 0.021 Uiso 1 1 calc R . . H2B H 0.4016 0.6837 0.8161 0.021 Uiso 1 1 calc R . . H2C H 0.5317 0.5674 0.8793 0.021 Uiso 1 1 calc R . . O3 O 0.74356(10) 0.48069(9) 0.92719(7) 0.01717(18) Uani 1 1 d . . . O4 O 1.01409(10) 0.40069(9) 0.92724(8) 0.01790(18) Uani 1 1 d . . . C9 C 0.88595(14) 0.48704(12) 0.88859(10) 0.0133(2) Uani 1 1 d . . . C10 C 0.90410(14) 0.60890(12) 0.78731(10) 0.0135(2) Uani 1 1 d . . . C11 C 1.02601(14) 0.66556(12) 0.77905(10) 0.0144(2) Uani 1 1 d . . . H11 H 1.0960 0.6263 0.8368 0.017 Uiso 1 1 calc R . . C12 C 1.04583(14) 0.77807(12) 0.68774(10) 0.0153(2) Uani 1 1 d . . . H12 H 1.1282 0.8161 0.6838 0.018 Uiso 1 1 calc R . . C13 C 0.94467(14) 0.83633(12) 0.60074(10) 0.0151(2) Uani 1 1 d . . . C14 C 0.82657(15) 0.77592(12) 0.60761(10) 0.0169(2) Uani 1 1 d . . . H14 H 0.7605 0.8112 0.5478 0.020 Uiso 1 1 calc R . . C15 C 0.80488(14) 0.66503(12) 0.70093(10) 0.0161(2) Uani 1 1 d . . . H15 H 0.7217 0.6274 0.7057 0.019 Uiso 1 1 calc R . . C16 C 0.95483(15) 0.95999(13) 0.50491(10) 0.0177(2) Uani 1 1 d . . . H16 H 0.8918 0.9853 0.4448 0.021 Uiso 1 1 calc R . . C17 C 0.77201(15) 0.05123(13) 0.81978(11) 0.0195(2) Uani 1 1 d . . . H17A H 0.6743 0.0774 0.7826 0.023 Uiso 1 1 calc R . . H17B H 0.8695 0.0259 0.7623 0.023 Uiso 1 1 calc R . . C18 C 0.77606(15) -0.07703(13) 0.92055(11) 0.0192(2) Uani 1 1 d . . . H18A H 0.6756 -0.0541 0.9762 0.023 Uiso 1 1 calc R . . H18B H 0.7777 -0.1554 0.8925 0.023 Uiso 1 1 calc R . . C19 C 0.40900(14) 0.36397(12) 0.85318(11) 0.0171(2) Uani 1 1 d . . . H19A H 0.4166 0.3091 0.7994 0.020 Uiso 1 1 calc R . . H19B H 0.2956 0.3887 0.8933 0.020 Uiso 1 1 calc R . . C20 C 0.44350(14) 0.49981(12) 0.78355(10) 0.0158(2) Uani 1 1 d . . . H20A H 0.5543 0.4757 0.7392 0.019 Uiso 1 1 calc R . . H20B H 0.3644 0.5535 0.7276 0.019 Uiso 1 1 calc R . . O1 O 0.15880(11) -0.01290(9) 0.83892(8) 0.02013(19) Uani 1 1 d . . . O2 O 0.36211(11) -0.13363(9) 0.72644(8) 0.01957(19) Uani 1 1 d . . . C1 C 0.27594(14) -0.02265(12) 0.75683(10) 0.0150(2) Uani 1 1 d . . . C2 C 0.31260(14) 0.11236(12) 0.68900(10) 0.0143(2) Uani 1 1 d . . . C3 C 0.46577(15) 0.10546(13) 0.62346(11) 0.0175(2) Uani 1 1 d . . . H3 H 0.5449 0.0159 0.6196 0.021 Uiso 1 1 calc R . . C4 C 0.50335(15) 0.22805(13) 0.56407(11) 0.0188(2) Uani 1 1 d . . . H4 H 0.6087 0.2214 0.5212 0.023 Uiso 1 1 calc R . . C5 C 0.38745(15) 0.36151(12) 0.56669(10) 0.0160(2) Uani 1 1 d . . . C6 C 0.23115(15) 0.36767(13) 0.62681(10) 0.0169(2) Uani 1 1 d . . . H6 H 0.1485 0.4571 0.6249 0.020 Uiso 1 1 calc R . . C7 C 0.19542(14) 0.24492(13) 0.68909(10) 0.0163(2) Uani 1 1 d . . . H7 H 0.0903 0.2513 0.7321 0.020 Uiso 1 1 calc R . . C8 C 0.42468(15) 0.49462(13) 0.51315(10) 0.0177(2) Uani 1 1 d . . . H8 H 0.3353 0.5794 0.4959 0.021 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 0.01279(14) 0.01257(14) 0.01983(15) -0.00287(11) -0.00193(11) -0.00256(11) S2 0.01420(15) 0.01258(14) 0.01720(15) -0.00326(11) -0.00112(10) -0.00425(11) N1 0.0150(5) 0.0108(4) 0.0200(5) -0.0017(4) -0.0006(4) -0.0048(4) N2 0.0143(5) 0.0123(4) 0.0142(5) -0.0019(4) -0.0015(4) -0.0040(4) O3 0.0148(4) 0.0176(4) 0.0169(4) -0.0008(3) 0.0004(3) -0.0074(3) O4 0.0162(4) 0.0122(4) 0.0220(4) 0.0012(3) -0.0043(3) -0.0047(3) C9 0.0159(5) 0.0110(5) 0.0134(5) -0.0035(4) -0.0008(4) -0.0051(4) C10 0.0128(5) 0.0107(5) 0.0138(5) -0.0028(4) 0.0013(4) -0.0027(4) C11 0.0130(5) 0.0128(5) 0.0154(5) -0.0027(4) -0.0018(4) -0.0028(4) C12 0.0139(5) 0.0134(5) 0.0181(5) -0.0030(4) -0.0005(4) -0.0058(4) C13 0.0165(5) 0.0121(5) 0.0141(5) -0.0017(4) 0.0002(4) -0.0047(4) C14 0.0177(6) 0.0170(6) 0.0150(5) -0.0014(4) -0.0038(4) -0.0059(5) C15 0.0154(5) 0.0159(5) 0.0174(5) -0.0029(4) -0.0013(4) -0.0072(4) C16 0.0200(6) 0.0160(5) 0.0147(5) -0.0001(4) -0.0032(4) -0.0060(5) C17 0.0194(6) 0.0165(6) 0.0224(6) -0.0077(5) -0.0057(5) -0.0016(5) C18 0.0144(5) 0.0146(5) 0.0295(6) -0.0079(5) -0.0030(5) -0.0039(4) C19 0.0131(5) 0.0156(5) 0.0229(6) -0.0054(5) -0.0047(4) -0.0033(4) C20 0.0148(5) 0.0152(5) 0.0158(5) -0.0050(4) -0.0025(4) -0.0019(4) O1 0.0209(4) 0.0194(4) 0.0195(4) -0.0033(3) 0.0035(3) -0.0113(4) O2 0.0220(4) 0.0130(4) 0.0211(4) -0.0020(3) -0.0016(3) -0.0057(3) C1 0.0156(5) 0.0150(5) 0.0151(5) -0.0011(4) -0.0040(4) -0.0068(4) C2 0.0164(5) 0.0144(5) 0.0128(5) -0.0017(4) -0.0024(4) -0.0072(4) C3 0.0162(6) 0.0144(5) 0.0199(6) -0.0038(4) -0.0003(4) -0.0048(4) C4 0.0172(6) 0.0177(6) 0.0197(6) -0.0044(5) 0.0026(4) -0.0075(5) C5 0.0208(6) 0.0154(5) 0.0127(5) -0.0026(4) -0.0008(4) -0.0087(5) C6 0.0183(6) 0.0140(5) 0.0175(5) -0.0041(4) -0.0016(4) -0.0046(4) C7 0.0152(5) 0.0177(6) 0.0163(5) -0.0049(4) 0.0005(4) -0.0067(4) C8 0.0231(6) 0.0144(5) 0.0150(5) -0.0032(4) 0.0002(4) -0.0076(5) _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 C17 1.8204(12) . ? S1 S2 2.0368(4) . ? S2 C19 1.8192(12) . ? N1 C18 1.4921(15) . ? N2 C20 1.4919(15) . ? O3 C9 1.2652(14) . ? O4 C9 1.2502(14) . ? C9 C10 1.5071(15) . ? C10 C15 1.3896(16) . ? C10 C11 1.3997(16) . ? C11 C12 1.3840(16) . ? C12 C13 1.4057(16) . ? C13 C14 1.4012(16) . ? C13 C16 1.4690(15) . ? C14 C15 1.3902(16) . ? C16 C16 1.337(2) 2_776 ? C17 C18 1.5116(17) . ? C19 C20 1.5187(16) . ? O1 C1 1.2667(15) . ? O2 C1 1.2515(15) . ? C1 C2 1.5151(15) . ? C2 C7 1.3943(16) . ? C2 C3 1.3994(17) . ? C3 C4 1.3882(16) . ? C4 C5 1.4019(17) . ? C5 C6 1.4018(17) . ? C5 C8 1.4749(16) . ? C6 C7 1.3886(16) . ? C8 C8 1.346(2) 2_666 ? 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 C17 S1 S2 101.80(4) . . ? C19 S2 S1 102.39(4) . . ? O4 C9 O3 125.67(10) . . ? O4 C9 C10 116.67(10) . . ? O3 C9 C10 117.67(10) . . ? C15 C10 C11 119.09(10) . . ? C15 C10 C9 121.80(10) . . ? C11 C10 C9 119.10(10) . . ? C12 C11 C10 120.81(11) . . ? C11 C12 C13 120.36(11) . . ? C14 C13 C12 118.47(10) . . ? C14 C13 C16 118.79(11) . . ? C12 C13 C16 122.72(11) . . ? C15 C14 C13 120.82(11) . . ? C10 C15 C14 120.39(11) . . ? C16 C16 C13 125.57(14) 2_776 . ? C18 C17 S1 113.76(9) . . ? N1 C18 C17 112.03(10) . . ? C20 C19 S2 114.41(8) . . ? N2 C20 C19 112.82(9) . . ? O2 C1 O1 125.56(11) . . ? O2 C1 C2 117.55(10) . . ? O1 C1 C2 116.89(10) . . ? C7 C2 C3 118.73(11) . . ? C7 C2 C1 121.26(10) . . ? C3 C2 C1 120.00(10) . . ? C4 C3 C2 120.74(11) . . ? C3 C4 C5 120.66(11) . . ? C6 C5 C4 118.21(11) . . ? C6 C5 C8 118.78(11) . . ? C4 C5 C8 122.97(11) . . ? C7 C6 C5 120.93(11) . . ? C6 C7 C2 120.55(11) . . ? C8 C8 C5 125.15(15) 2_666 . ? 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 O1 0.91 1.89 2.7764(13) 165.3 1_655 N1 H1B O4 0.91 1.75 2.6561(13) 172.9 2_757 N1 H1C O1 0.91 1.94 2.8488(14) 179.6 2_657 N2 H2A O3 0.91 1.90 2.7794(13) 163.4 2_667 N2 H2B O2 0.91 1.84 2.7423(13) 173.9 1_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.486 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.058 #===END data_compound_6 _database_code_depnum_ccdc_archive 'CCDC 779314' #data_8566a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H15 N3 O4' _chemical_formula_weight 229.24 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.6939(8) _cell_length_b 10.6964(7) _cell_length_c 8.8496(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.170(2) _cell_angle_gamma 90.00 _cell_volume 1105.24(13) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3022 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 27.41 _exptl_crystal_description Rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9414 _exptl_absorpt_correction_T_max 0.9892 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7613 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2529 _reflns_number_gt 2279 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0730P)^2^+0.3405P] 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 2529 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1294 _refine_ls_wR_factor_gt 0.1260 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.24914(10) 0.58439(10) 0.69110(12) 0.0329(3) Uani 1 1 d . . . O2 O 0.25937(10) 0.37841(9) 0.66827(11) 0.0327(3) Uani 1 1 d . . . N1 N 0.12653(11) 0.08096(12) 0.68412(14) 0.0287(3) Uani 1 1 d . . . H1A H 0.0907 0.0192 0.7247 0.034 Uiso 1 1 calc R . . H1B H 0.1360 0.1511 0.7331 0.034 Uiso 1 1 calc R . . N2 N 0.15264(11) -0.03799(11) 0.47209(14) 0.0290(3) Uani 1 1 d . . . H2A H 0.1779 -0.0455 0.3819 0.035 Uiso 1 1 calc R . . H2B H 0.1180 -0.1004 0.5130 0.035 Uiso 1 1 calc R . . N3 N 0.21955(11) 0.16298(11) 0.48433(13) 0.0278(3) Uani 1 1 d . . . H3A H 0.2448 0.1552 0.3941 0.033 Uiso 1 1 calc R . . H3B H 0.2290 0.2330 0.5334 0.033 Uiso 1 1 calc R . . C1 C 0.27749(11) 0.48754(13) 0.62193(15) 0.0223(3) Uani 1 1 d . . . C2 C 0.33269(11) 0.50250(12) 0.47320(14) 0.0202(3) Uani 1 1 d . . . C3 C 0.32189(12) 0.61412(12) 0.39275(15) 0.0228(3) Uani 1 1 d . . . H3 H 0.2836 0.6822 0.4341 0.027 Uiso 1 1 calc R . . C4 C 0.36733(12) 0.62544(12) 0.25189(15) 0.0238(3) Uani 1 1 d . . . H4 H 0.3582 0.7009 0.1981 0.029 Uiso 1 1 calc R . . C5 C 0.42646(11) 0.52640(13) 0.18861(15) 0.0220(3) Uani 1 1 d . . . C6 C 0.43889(11) 0.41553(13) 0.27179(16) 0.0233(3) Uani 1 1 d . . . H6 H 0.4792 0.3481 0.2322 0.028 Uiso 1 1 calc R . . C7 C 0.39250(11) 0.40401(12) 0.41164(15) 0.0217(3) Uani 1 1 d . . . H7 H 0.4015 0.3287 0.4658 0.026 Uiso 1 1 calc R . . C8 C 0.47085(12) 0.54214(13) 0.03762(16) 0.0254(3) Uani 1 1 d . . . H8 H 0.4567 0.6193 -0.0106 0.030 Uiso 1 1 calc R . . C9 C 0.16683(11) 0.06821(12) 0.54692(15) 0.0221(3) Uani 1 1 d . . . O1W O 0.06749(11) 0.72857(11) 0.59504(13) 0.0347(3) Uani 1 1 d . . . H1WA H 0.037(2) 0.768(2) 0.675(3) 0.062(7) Uiso 1 1 d . . . H2WA H -0.009(2) 0.351(2) 0.590(3) 0.057(7) Uiso 1 1 d . . . O2W O 0.01132(11) 0.37546(12) 0.67625(14) 0.0362(3) Uani 1 1 d . . . H1WB H 0.129(2) 0.684(2) 0.630(3) 0.059(6) Uiso 1 1 d . . . H2WB H 0.083(3) 0.392(2) 0.681(3) 0.065(7) 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 0.0457(7) 0.0298(6) 0.0245(5) -0.0009(4) 0.0136(5) 0.0068(5) O2 0.0511(7) 0.0253(5) 0.0233(5) -0.0020(4) 0.0156(5) -0.0086(4) N1 0.0357(7) 0.0291(6) 0.0219(6) -0.0021(5) 0.0076(5) -0.0005(5) N2 0.0401(7) 0.0259(6) 0.0215(6) -0.0020(5) 0.0076(5) -0.0076(5) N3 0.0376(7) 0.0234(6) 0.0231(6) -0.0031(4) 0.0084(5) -0.0038(5) C1 0.0227(6) 0.0264(7) 0.0181(6) -0.0012(5) 0.0037(5) -0.0025(5) C2 0.0200(6) 0.0230(6) 0.0178(6) -0.0017(5) 0.0033(5) -0.0034(5) C3 0.0260(7) 0.0206(6) 0.0223(6) -0.0024(5) 0.0056(5) 0.0000(5) C4 0.0275(7) 0.0217(6) 0.0226(7) 0.0032(5) 0.0044(5) -0.0009(5) C5 0.0201(6) 0.0269(7) 0.0194(6) 0.0001(5) 0.0051(5) -0.0033(5) C6 0.0228(6) 0.0247(7) 0.0232(7) -0.0003(5) 0.0075(5) 0.0020(5) C7 0.0228(6) 0.0216(6) 0.0212(6) 0.0022(5) 0.0049(5) -0.0009(5) C8 0.0279(7) 0.0270(7) 0.0220(7) 0.0040(5) 0.0078(5) -0.0020(5) C9 0.0213(6) 0.0249(7) 0.0200(6) 0.0001(5) 0.0009(5) 0.0024(5) O1W 0.0393(6) 0.0332(6) 0.0319(6) 0.0014(5) 0.0054(5) 0.0040(5) O2W 0.0340(6) 0.0434(7) 0.0318(6) -0.0067(5) 0.0089(5) -0.0079(5) _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 1.2571(17) . ? O2 C1 1.2591(17) . ? N1 C9 1.3335(18) . ? N2 C9 1.3207(18) . ? N3 C9 1.3238(18) . ? C1 C2 1.5061(18) . ? C2 C7 1.3921(18) . ? C2 C3 1.3922(19) . ? C3 C4 1.3871(19) . ? C4 C5 1.3988(19) . ? C5 C6 1.3991(19) . ? C5 C8 1.4696(18) . ? C6 C7 1.3840(18) . ? C8 C8 1.331(3) 3_665 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 123.48(12) . . ? O1 C1 C2 118.38(12) . . ? O2 C1 C2 118.11(12) . . ? C7 C2 C3 118.83(12) . . ? C7 C2 C1 120.69(11) . . ? C3 C2 C1 120.46(12) . . ? C4 C3 C2 120.40(12) . . ? C3 C4 C5 121.07(12) . . ? C4 C5 C6 118.07(12) . . ? C4 C5 C8 118.98(12) . . ? C6 C5 C8 122.94(12) . . ? C7 C6 C5 120.76(12) . . ? C6 C7 C2 120.85(12) . . ? C8 C8 C5 126.43(17) 3_665 . ? N2 C9 N3 119.82(12) . . ? N2 C9 N1 120.24(13) . . ? N3 C9 N1 119.93(12) . . ? 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 O2W 0.87 2.16 3.0295(18) 175.1 2_546 N2 H2A O1 0.87 1.97 2.8308(16) 171.1 4_565 N2 H2B O1W 0.87 2.07 2.9206(17) 167.0 1_545 N3 H3A O2 0.87 2.05 2.8948(15) 164.4 4_565 N3 H3B O2 0.87 1.98 2.8448(16) 172.2 . O1W H1WA O2W 0.91(3) 1.86(3) 2.7605(17) 169(2) 2_556 O2W H2WA O1W 0.83(3) 1.94(3) 2.7580(17) 171(2) 3_566 O1W H1WB O1 0.90(3) 1.82(3) 2.7228(17) 175(2) . O2W H2WB O2 0.85(3) 2.08(3) 2.9057(18) 163(2) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.334 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.111 #===END data_compound_7 _database_code_depnum_ccdc_archive 'CCDC 779315' #data_9171 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H30 N4 O6' _chemical_formula_weight 494.54 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 P2(1)/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 8.5009(6) _cell_length_b 10.6106(7) _cell_length_c 13.7800(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.6510(10) _cell_angle_gamma 90.00 _cell_volume 1217.34(14) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3735 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.47 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.70 _exptl_crystal_size_min 0.56 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9091 _exptl_absorpt_correction_T_max 0.9476 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8398 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2783 _reflns_number_gt 2386 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0981P)^2^+0.3825P] 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 2783 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1709 _refine_ls_wR_factor_gt 0.1652 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.31958(16) 0.37462(11) 0.45787(9) 0.0483(3) Uani 1 1 d . . . O2 O 0.22768(14) 0.57027(11) 0.43687(8) 0.0442(3) Uani 1 1 d . . . N1 N 0.16439(17) 0.53177(14) 0.61327(10) 0.0422(3) Uani 1 1 d . . . H1N H 0.192(3) 0.543(2) 0.5476(17) 0.063(6) Uiso 1 1 d . . . N2 N 0.06751(17) 0.51001(15) 0.89253(10) 0.0449(4) Uani 1 1 d . . . H2A H 0.0295 0.4329 0.9023 0.067 Uiso 1 1 calc R . . H2B H -0.0065 0.5685 0.8988 0.067 Uiso 1 1 calc R . . H2C H 0.1581 0.5244 0.9377 0.067 Uiso 1 1 calc R . . C1 C 0.29502(18) 0.47397(15) 0.40916(11) 0.0371(3) Uani 1 1 d . . . C8 C 0.5062(7) 0.4567(6) 0.0352(5) 0.040(2) Uani 0.306(8) 1 d P . 1 H8 H 0.5599 0.3820 0.0247 0.049 Uiso 0.306(8) 1 calc PR . 1 C2 C 0.3527(12) 0.4676(8) 0.3124(5) 0.0364(10) Uani 0.306(8) 1 d PG . 1 C3 C 0.4372(11) 0.3651(7) 0.2864(4) 0.0364(10) Uani 0.306(8) 1 d PG . 1 H3 H 0.4634 0.2972 0.3305 0.044 Uiso 0.306(8) 1 calc PR . 1 C4 C 0.4831(8) 0.3631(7) 0.1951(4) 0.0364(10) Uani 0.306(8) 1 d PG . 1 H4 H 0.5403 0.2938 0.1775 0.044 Uiso 0.306(8) 1 calc PR . 1 C5 C 0.4445(7) 0.4635(7) 0.1299(3) 0.0364(10) Uani 0.306(8) 1 d PG . 1 C6 C 0.3600(8) 0.5660(6) 0.1560(4) 0.0364(10) Uani 0.306(8) 1 d PG . 1 H6 H 0.3338 0.6340 0.1118 0.044 Uiso 0.306(8) 1 calc PR . 1 C7 C 0.3141(10) 0.5681(7) 0.2472(5) 0.0358(16) Uani 0.306(8) 1 d PG . 1 H7 H 0.2569 0.6374 0.2648 0.043 Uiso 0.306(8) 1 calc PR . 1 C9 C 0.0891(2) 0.62664(16) 0.64895(12) 0.0422(4) Uani 1 1 d . . . H9 H 0.0585 0.6978 0.6089 0.051 Uiso 1 1 calc R . . C10 C 0.05561(19) 0.62336(15) 0.74116(12) 0.0401(4) Uani 1 1 d . . . H10 H 0.0037 0.6918 0.7646 0.048 Uiso 1 1 calc R . . C11 C 0.09932(18) 0.51631(14) 0.80185(11) 0.0370(3) Uani 1 1 d . . . C12 C 0.1767(2) 0.41772(16) 0.76160(13) 0.0452(4) Uani 1 1 d . . . H12 H 0.2067 0.3441 0.7987 0.054 Uiso 1 1 calc R . . C13 C 0.2082(2) 0.42899(17) 0.66896(13) 0.0471(4) Uani 1 1 d . . . H13 H 0.2619 0.3633 0.6434 0.056 Uiso 1 1 calc R . . O1W O 0.57515(18) 0.21774(12) 0.51498(10) 0.0501(3) Uani 1 1 d . . . H1WA H 0.647(3) 0.275(2) 0.5394(17) 0.065(7) Uiso 1 1 d . . . H1WB H 0.491(4) 0.265(3) 0.4908(19) 0.083(8) Uiso 1 1 d . . . C8A C 0.4508(3) 0.5343(3) 0.0213(2) 0.0384(9) Uani 0.694(8) 1 d P . 2 H8A H 0.4013 0.6036 -0.0150 0.046 Uiso 0.694(8) 1 calc PR . 2 C2B C 0.3385(5) 0.4890(3) 0.30710(18) 0.0330(6) Uani 0.694(8) 1 d PG . 2 C3B C 0.4232(4) 0.3943(3) 0.2702(2) 0.0391(7) Uani 0.694(8) 1 d PG . 2 H3B H 0.4559 0.3221 0.3085 0.047 Uiso 0.694(8) 1 calc PR . 2 C4B C 0.4594(3) 0.4064(3) 0.1767(2) 0.0397(7) Uani 0.694(8) 1 d PG . 2 H4B H 0.5166 0.3424 0.1518 0.048 Uiso 0.694(8) 1 calc PR . 2 C5B C 0.4110(3) 0.5132(4) 0.12009(15) 0.0344(7) Uani 0.694(8) 1 d PG . 2 C6B C 0.3264(3) 0.6079(3) 0.15696(17) 0.0379(6) Uani 0.694(8) 1 d PG . 2 H6B H 0.2937 0.6801 0.1187 0.045 Uiso 0.694(8) 1 calc PR . 2 C7B C 0.2902(4) 0.5958(3) 0.2505(2) 0.0381(7) Uani 0.694(8) 1 d PG . 2 H7B H 0.2330 0.6598 0.2754 0.046 Uiso 0.694(8) 1 calc PR . 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 O1 0.0621(8) 0.0428(7) 0.0426(6) 0.0058(5) 0.0167(6) 0.0034(5) O2 0.0534(7) 0.0401(6) 0.0425(6) -0.0020(5) 0.0177(5) -0.0003(5) N1 0.0462(8) 0.0447(8) 0.0378(7) -0.0008(6) 0.0134(6) -0.0045(6) N2 0.0491(8) 0.0479(8) 0.0383(7) 0.0023(6) 0.0107(6) 0.0011(6) C1 0.0390(8) 0.0387(8) 0.0338(7) -0.0020(6) 0.0081(6) -0.0051(6) C8 0.047(3) 0.041(4) 0.036(4) -0.003(3) 0.014(2) 0.002(3) C2 0.051(2) 0.027(2) 0.0316(15) 0.0070(14) 0.0097(13) 0.0038(16) C3 0.051(2) 0.027(2) 0.0316(15) 0.0070(14) 0.0097(13) 0.0038(16) C4 0.051(2) 0.027(2) 0.0316(15) 0.0070(14) 0.0097(13) 0.0038(16) C5 0.051(2) 0.027(2) 0.0316(15) 0.0070(14) 0.0097(13) 0.0038(16) C6 0.051(2) 0.027(2) 0.0316(15) 0.0070(14) 0.0097(13) 0.0038(16) C7 0.038(3) 0.026(3) 0.043(4) -0.001(2) 0.008(2) 0.001(2) C9 0.0456(8) 0.0389(8) 0.0418(8) 0.0056(6) 0.0082(7) -0.0025(6) C10 0.0435(8) 0.0354(8) 0.0421(8) 0.0000(6) 0.0102(6) 0.0028(6) C11 0.0358(7) 0.0375(8) 0.0369(7) 0.0005(6) 0.0059(6) -0.0035(6) C12 0.0525(9) 0.0375(8) 0.0470(9) 0.0049(7) 0.0134(7) 0.0049(7) C13 0.0521(9) 0.0411(9) 0.0508(9) -0.0043(7) 0.0174(7) 0.0027(7) O1W 0.0598(8) 0.0359(6) 0.0524(7) -0.0023(5) 0.0061(6) -0.0018(6) C8A 0.0432(13) 0.0378(15) 0.0340(15) 0.0027(9) 0.0072(11) -0.0006(11) C2B 0.0310(12) 0.0345(15) 0.0339(12) -0.0044(10) 0.0070(9) -0.0051(10) C3B 0.0504(14) 0.0305(14) 0.0368(14) 0.0072(9) 0.0101(12) 0.0041(11) C4B 0.0527(14) 0.0303(15) 0.0391(14) 0.0031(11) 0.0163(11) 0.0079(12) C5B 0.0384(12) 0.0322(16) 0.0316(11) 0.0027(10) 0.0045(9) -0.0059(11) C6B 0.0412(13) 0.0314(14) 0.0403(12) 0.0063(10) 0.0065(10) 0.0008(10) C7B 0.0430(16) 0.0351(16) 0.0372(15) 0.0010(11) 0.0098(11) 0.0038(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 O1 C1 1.2446(19) . ? O2 C1 1.2672(19) . ? N1 C9 1.339(2) . ? N1 C13 1.342(2) . ? N2 C11 1.333(2) . ? C1 C2 1.512(4) . ? C1 C2B 1.533(2) . ? C8 C8 1.326(14) 3_665 ? C8 C5 1.503(8) . ? C2 C3 1.3900 . ? C2 C7 1.3900 . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C6 C7 1.3900 . ? C9 C10 1.358(2) . ? C10 C11 1.415(2) . ? C11 C12 1.408(2) . ? C12 C13 1.362(2) . ? C8A C8A 1.332(6) 3_665 ? C8A C5B 1.484(4) . ? C2B C3B 1.3900 . ? C2B C7B 1.3900 . ? C3B C4B 1.3900 . ? C4B C5B 1.3900 . ? C5B C6B 1.3900 . ? C6B C7B 1.3900 . ? 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 C9 N1 C13 119.94(15) . . ? O1 C1 O2 123.86(14) . . ? O1 C1 C2 112.9(3) . . ? O2 C1 C2 123.2(3) . . ? O1 C1 C2B 122.52(16) . . ? O2 C1 C2B 113.57(15) . . ? C2 C1 C2B 9.8(3) . . ? C8 C8 C5 127.8(8) 3_665 . ? C3 C2 C7 120.0 . . ? C3 C2 C1 122.6(4) . . ? C7 C2 C1 117.4(4) . . ? C2 C3 C4 120.0 . . ? C5 C4 C3 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 C8 116.5(4) . . ? C6 C5 C8 123.4(4) . . ? C7 C6 C5 120.0 . . ? C6 C7 C2 120.0 . . ? N1 C9 C10 122.05(15) . . ? C9 C10 C11 119.61(15) . . ? N2 C11 C12 122.11(15) . . ? N2 C11 C10 121.04(15) . . ? C12 C11 C10 116.84(15) . . ? C13 C12 C11 120.01(15) . . ? N1 C13 C12 121.53(16) . . ? C8A C8A C5B 127.0(3) 3_665 . ? C3B C2B C7B 120.0 . . ? C3B C2B C1 119.91(15) . . ? C7B C2B C1 120.07(15) . . ? C4B C3B C2B 120.0 . . ? C3B C4B C5B 120.0 . . ? C6B C5B C4B 120.0 . . ? C6B C5B C8A 117.2(2) . . ? C4B C5B C8A 122.8(2) . . ? C5B C6B C7B 120.0 . . ? C6B C7B C2B 120.0 . . ? 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 H1N O2 0.99(2) 1.64(2) 2.6255(18) 176(2) . N1 H1N O1 0.99(2) 2.54(2) 3.2011(19) 124.5(17) . N2 H2B O1W 0.90 2.13 2.929(2) 147.3 2_556 N2 H2A O1W 0.90 2.21 2.9405(19) 138.3 4_566 O1W H1WA O2 0.88(3) 1.94(3) 2.8036(18) 164(2) 3_666 O1W H1WB O1 0.88(3) 1.85(3) 2.7239(19) 172(2) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.391 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.048 #===END data_compound_8 _database_code_depnum_ccdc_archive 'CCDC 779316' #data_9224a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 N2 O4' _chemical_formula_weight 354.40 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.5672(16) _cell_length_b 8.3029(10) _cell_length_c 8.2837(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.708(3) _cell_angle_gamma 90.00 _cell_volume 861.44(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2543 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 27.33 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9465 _exptl_absorpt_correction_T_max 0.9943 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5803 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 27.45 _reflns_number_total 1956 _reflns_number_gt 1802 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+0.3526P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1956 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1244 _refine_ls_wR_factor_gt 0.1222 _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_restrained_S_all 1.130 _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 N1 N 0.58057(9) 0.53714(14) 0.39329(14) 0.0215(3) Uani 1 1 d . . . H1A H 0.6205 0.5092 0.3094 0.026 Uiso 1 1 calc R . . H1B H 0.6010 0.6388 0.4275 0.026 Uiso 1 1 calc R . . C9 C 0.60229(11) 0.42162(18) 0.52872(17) 0.0229(3) Uani 1 1 d . . . H9A H 0.6787 0.4268 0.5682 0.027 Uiso 1 1 calc R . . H9B H 0.5865 0.3108 0.4898 0.027 Uiso 1 1 calc R . . C10 C 0.46561(11) 0.53909(18) 0.33433(16) 0.0233(3) Uani 1 1 d . . . H10A H 0.4449 0.4325 0.2884 0.028 Uiso 1 1 calc R . . H10B H 0.4534 0.6205 0.2475 0.028 Uiso 1 1 calc R . . O1 O 0.68652(9) 0.44415(13) 0.15067(13) 0.0319(3) Uani 1 1 d . . . O2 O 0.62669(8) 0.67210(13) 0.03543(13) 0.0270(3) Uani 1 1 d . . . C1 C 0.68620(11) 0.55063(17) 0.04248(16) 0.0205(3) Uani 1 1 d . . . C2 C 0.76381(10) 0.52718(17) -0.08537(16) 0.0191(3) Uani 1 1 d . . . C3 C 0.80947(11) 0.37699(18) -0.10639(17) 0.0234(3) Uani 1 1 d . . . H3 H 0.7924 0.2897 -0.0389 0.028 Uiso 1 1 calc R . . C4 C 0.87975(12) 0.35328(18) -0.22507(18) 0.0245(3) Uani 1 1 d . . . H4 H 0.9088 0.2491 -0.2394 0.029 Uiso 1 1 calc R . . C5 C 0.90855(11) 0.47943(17) -0.32354(16) 0.0208(3) Uani 1 1 d . . . C6 C 0.86296(11) 0.63098(17) -0.30086(17) 0.0229(3) Uani 1 1 d . . . H6 H 0.8815 0.7192 -0.3659 0.027 Uiso 1 1 calc R . . C7 C 0.79116(11) 0.65345(17) -0.18466(17) 0.0221(3) Uani 1 1 d . . . H7 H 0.7601 0.7566 -0.1725 0.026 Uiso 1 1 calc R . . C8 C 0.98404(12) 0.44790(18) -0.44611(17) 0.0238(3) Uani 1 1 d . . . H8 H 1.0130 0.3423 -0.4486 0.029 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 N1 0.0237(6) 0.0227(6) 0.0195(6) -0.0023(4) 0.0104(4) -0.0033(5) C9 0.0220(7) 0.0241(7) 0.0229(7) 0.0002(5) 0.0045(5) 0.0025(5) C10 0.0266(7) 0.0270(7) 0.0167(6) 0.0018(5) 0.0045(5) -0.0007(6) O1 0.0436(7) 0.0290(6) 0.0263(6) 0.0076(4) 0.0215(5) 0.0105(5) O2 0.0295(5) 0.0253(5) 0.0279(5) 0.0032(4) 0.0135(4) 0.0067(4) C1 0.0222(7) 0.0229(7) 0.0174(6) -0.0014(5) 0.0070(5) -0.0001(5) C2 0.0192(6) 0.0232(7) 0.0156(6) -0.0006(5) 0.0050(5) 0.0005(5) C3 0.0280(7) 0.0221(7) 0.0215(7) 0.0039(5) 0.0103(5) 0.0016(5) C4 0.0272(7) 0.0231(7) 0.0245(7) 0.0009(5) 0.0100(6) 0.0055(5) C5 0.0203(6) 0.0257(7) 0.0173(6) -0.0006(5) 0.0065(5) 0.0007(5) C6 0.0260(7) 0.0228(7) 0.0210(7) 0.0039(5) 0.0095(5) 0.0013(5) C7 0.0238(7) 0.0218(7) 0.0217(7) 0.0009(5) 0.0079(5) 0.0034(5) C8 0.0251(7) 0.0260(7) 0.0215(7) -0.0009(5) 0.0100(5) 0.0041(5) _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 N1 C9 1.4842(18) . ? N1 C10 1.4867(18) . ? C9 C10 1.5101(19) 3_666 ? C10 C9 1.5101(19) 3_666 ? O1 C1 1.2587(17) . ? O2 C1 1.2541(17) . ? C1 C2 1.5101(17) . ? C2 C3 1.390(2) . ? C2 C7 1.3929(19) . ? C3 C4 1.3885(18) . ? C4 C5 1.394(2) . ? C5 C6 1.402(2) . ? C5 C8 1.4689(18) . ? C6 C7 1.3850(18) . ? C8 C8 1.329(3) 3_764 ? 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 C9 N1 C10 111.64(11) . . ? N1 C9 C10 110.36(11) . 3_666 ? N1 C10 C9 110.45(11) . 3_666 ? O2 C1 O1 124.40(12) . . ? O2 C1 C2 119.22(12) . . ? O1 C1 C2 116.38(12) . . ? C3 C2 C7 118.49(12) . . ? C3 C2 C1 120.05(12) . . ? C7 C2 C1 121.46(12) . . ? C4 C3 C2 120.61(13) . . ? C3 C4 C5 121.25(13) . . ? C4 C5 C6 117.88(12) . . ? C4 C5 C8 118.96(13) . . ? C6 C5 C8 123.16(13) . . ? C7 C6 C5 120.72(13) . . ? C6 C7 C2 121.03(13) . . ? C8 C8 C5 126.59(18) 3_764 . ? 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 O1 0.92 1.70 2.6167(15) 174.9 . N1 H1A O2 0.92 2.65 3.2652(15) 125.1 . N1 H1B O2 0.92 1.82 2.7273(16) 167.2 4_576 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.290 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.059 #===END