# Electronic Supplementary Material (ESI) for Analytical Methods # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Methods _journal_coden_cambridge 1222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Bojidarka Ivanova' _publ_contact_author_email BIvanova@chem.uni-sofia.bg loop_ _publ_author_name 'Bojidarka Ivanova' 'Michael Spiteller' data_scan_0m_p21_c _database_code_depnum_ccdc_archive 'CCDC 760138' #TrackingRef '- Struct-1.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Univ.Prof. Dr. Dr. h.c. Michael Spiteller' 'Institut fur Umweltforschung (INFU)' 'Technische Universitat Dortmund' '44227 Dortmund' 'Otto-Hahn-Str. 6' 'Tel: +49 231 755 4080' 'Fax: +49 231 755 4085' 'E-mail: spiteller@infu.uni-dortmund.de' 'Hompage INFU: http://www.infu.tu-dortmund.de/' 'Dr. Bojidarka Ivanova' 'Institut fur Umweltforschung (INFU)' 'Technische Universitat Dortmund (TU Dortmund)' '44227 Dortmund' 'Otto-Hahn-Str. 6' 'Tel: +49 231 755 4089' 'Fax: +49 231 755 4085' 'E-mail: B.Ivanova@infu.uni-dortmund.de' 'Hompage INFU: http://www.infu.tu-dortmund.de/' ; _chemical_name_common ; 'Univ.Prof. Dr. Dr. h.c. Michael Spiteller' 'Institut fur Umweltforschung (INFU)' 'Technische Universitat Dortmund' '44227 Dortmund' 'Otto-Hahn-Str. 6' 'Tel ; _chemical_melting_point ? _chemical_formula_moiety '(C4 H O4), (C12 H10 N O)' _chemical_formula_sum 'C16 H11 N O5' _chemical_formula_weight 297.26 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 P12(1)/c1 _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.7822(18) _cell_length_b 7.2392(9) _cell_length_c 12.5086(17) _cell_angle_alpha 90.00 _cell_angle_beta 106.033(4) _cell_angle_gamma 90.00 _cell_volume 1373.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 2426 _cell_measurement_theta_min 1.34 _cell_measurement_theta_max 25.00 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7595 _exptl_absorpt_correction_T_max 0.9914 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'micro-focus sealed tube' _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_measurement_device_type 'Bruker SMART X2S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8370 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2426 _reflns_number_gt 1825 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker GIS' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker APEX2' _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^)+(0.0796P)^2^+0.3501P] 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 2426 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1301 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.005 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 -0.04112(9) 1.0702(3) 0.11042(12) 0.0665(5) Uani 1 1 d . . . O2 O -0.12145(10) 0.9494(3) 0.42761(12) 0.0630(5) Uani 1 1 d . . . O3 O -0.22525(11) 0.9640(3) 0.16728(14) 0.0697(5) Uani 1 1 d . . . O4 O 0.06119(10) 1.0691(3) 0.36507(13) 0.0703(5) Uani 1 1 d . . . H4 H 0.0674 1.0647 0.4323 0.105 Uiso 1 1 calc R . . O5 O 0.35982(10) 0.8350(2) 1.45370(11) 0.0600(5) Uani 1 1 d . . . N1 N 0.16529(11) 0.9290(2) 1.08127(14) 0.0459(4) Uani 1 1 d . . . H1 H 0.1208 0.9445 1.0241 0.055 Uiso 1 1 calc R . . C1 C -0.06487(13) 1.0389(3) 0.19624(16) 0.0477(5) Uani 1 1 d . . . C2 C -0.02142(13) 1.0358(3) 0.31189(17) 0.0465(5) Uani 1 1 d . . . C3 C -0.09995(13) 0.9849(3) 0.34107(16) 0.0431(5) Uani 1 1 d . . . C4 C -0.14910(14) 0.9885(3) 0.22120(17) 0.0462(5) Uani 1 1 d . . . C5 C 0.16456(13) 1.0071(3) 1.17786(17) 0.0474(5) Uani 1 1 d . . . H5 H 0.1165 1.0777 1.1824 0.057 Uiso 1 1 calc R . . C6 C 0.23420(13) 0.9834(3) 1.26963(17) 0.0427(5) Uani 1 1 d . . . H6 H 0.2333 1.0366 1.3370 0.051 Uiso 1 1 calc R . . C7 C 0.30655(12) 0.8796(2) 1.26238(15) 0.0349(4) Uani 1 1 d . . . C8 C 0.37970(13) 0.8458(2) 1.36670(15) 0.0384(4) Uani 1 1 d . . . C9 C 0.47332(12) 0.8248(2) 1.36488(15) 0.0358(4) Uani 1 1 d . . . C10 C 0.53155(14) 0.7427(3) 1.45583(17) 0.0478(5) Uani 1 1 d . . . H10 H 0.5112 0.6985 1.5140 0.057 Uiso 1 1 calc R . . C11 C 0.61982(15) 0.7261(3) 1.4608(2) 0.0591(6) Uani 1 1 d . . . H11 H 0.6585 0.6698 1.5219 0.071 Uiso 1 1 calc R . . C12 C 0.65048(14) 0.7928(3) 1.3753(2) 0.0573(6) Uani 1 1 d . . . H12 H 0.7100 0.7830 1.3793 0.069 Uiso 1 1 calc R . . C13 C 0.30505(12) 0.8012(2) 1.16065(16) 0.0388(4) Uani 1 1 d . . . H13 H 0.3525 0.7313 1.1532 0.047 Uiso 1 1 calc R . . C14 C 0.23328(13) 0.8275(3) 1.07144(16) 0.0443(5) Uani 1 1 d . . . H14 H 0.2318 0.7742 1.0033 0.053 Uiso 1 1 calc R . . C15 C 0.59351(13) 0.8737(3) 1.28428(19) 0.0497(5) Uani 1 1 d . . . H15 H 0.6145 0.9175 1.2265 0.060 Uiso 1 1 calc R . . C16 C 0.50484(13) 0.8904(2) 1.27822(16) 0.0407(5) Uani 1 1 d . . . H16 H 0.4664 0.9453 1.2164 0.049 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 0.0370(9) 0.1233(14) 0.0365(8) 0.0087(8) 0.0059(7) -0.0034(8) O2 0.0385(9) 0.1104(13) 0.0383(8) -0.0005(8) 0.0078(7) -0.0113(8) O3 0.0367(9) 0.1145(14) 0.0493(9) 0.0018(9) -0.0027(8) -0.0168(9) O4 0.0328(9) 0.1364(15) 0.0377(8) 0.0006(10) 0.0032(7) -0.0145(9) O5 0.0496(10) 0.0988(12) 0.0336(8) 0.0066(8) 0.0145(7) -0.0022(8) N1 0.0285(9) 0.0660(10) 0.0394(10) 0.0106(8) 0.0027(8) 0.0011(8) C1 0.0343(12) 0.0703(13) 0.0356(11) 0.0013(9) 0.0049(10) 0.0010(10) C2 0.0297(11) 0.0690(13) 0.0379(11) -0.0014(9) 0.0044(9) -0.0009(9) C3 0.0326(11) 0.0593(12) 0.0352(10) -0.0035(9) 0.0056(9) -0.0005(9) C4 0.0357(12) 0.0595(12) 0.0409(11) -0.0013(9) 0.0063(10) -0.0023(9) C5 0.0326(11) 0.0619(12) 0.0501(13) 0.0069(10) 0.0153(11) 0.0074(9) C6 0.0361(11) 0.0554(11) 0.0387(11) -0.0029(9) 0.0139(10) 0.0023(9) C7 0.0302(10) 0.0407(9) 0.0344(10) 0.0033(7) 0.0101(9) -0.0018(7) C8 0.0392(11) 0.0425(10) 0.0332(10) 0.0011(8) 0.0098(9) -0.0021(8) C9 0.0320(10) 0.0366(9) 0.0350(10) -0.0015(7) 0.0028(9) 0.0009(7) C10 0.0477(13) 0.0508(11) 0.0381(11) 0.0007(9) 0.0006(10) 0.0040(9) C11 0.0469(14) 0.0611(13) 0.0545(13) -0.0063(11) -0.0107(12) 0.0145(11) C12 0.0314(11) 0.0577(13) 0.0772(17) -0.0192(12) 0.0057(12) 0.0055(10) C13 0.0332(10) 0.0475(10) 0.0355(10) 0.0016(8) 0.0091(9) 0.0046(8) C14 0.0380(12) 0.0614(12) 0.0322(10) 0.0008(9) 0.0077(10) 0.0020(9) C15 0.0399(12) 0.0497(11) 0.0628(14) -0.0066(10) 0.0197(12) -0.0038(9) C16 0.0357(11) 0.0417(10) 0.0427(11) 0.0024(8) 0.0077(10) 0.0016(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 O1 C1 1.251(2) . ? O2 C3 1.247(2) . ? O3 C4 1.218(2) . ? O4 C2 1.312(2) . ? O4 H4 0.8200 . ? O5 C8 1.215(2) . ? N1 C14 1.334(2) . ? N1 C5 1.337(3) . ? N1 H1 0.8600 . ? C1 C2 1.420(3) . ? C1 C4 1.492(3) . ? C2 C3 1.434(3) . ? C3 C4 1.486(3) . ? C5 C6 1.363(3) . ? C5 H5 0.9300 . ? C6 C7 1.391(3) . ? C6 H6 0.9300 . ? C7 C13 1.387(2) . ? C7 C8 1.504(3) . ? C8 C9 1.492(3) . ? C9 C10 1.384(3) . ? C9 C16 1.395(2) . ? C10 C11 1.382(3) . ? C10 H10 0.9300 . ? C11 C12 1.377(3) . ? C11 H11 0.9300 . ? C12 C15 1.372(3) . ? C12 H12 0.9300 . ? C13 C14 1.366(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.386(3) . ? C15 H15 0.9300 . ? C16 H16 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 C2 O4 H4 109.5 . . ? C14 N1 C5 121.62(18) . . ? C14 N1 H1 119.2 . . ? C5 N1 H1 119.2 . . ? O1 C1 C2 134.59(19) . . ? O1 C1 C4 136.0(2) . . ? C2 C1 C4 89.45(16) . . ? O4 C2 C1 130.27(18) . . ? O4 C2 C3 136.56(19) . . ? C1 C2 C3 93.17(17) . . ? O2 C3 C2 137.3(2) . . ? O2 C3 C4 133.48(18) . . ? C2 C3 C4 89.18(15) . . ? O3 C4 C1 136.0(2) . . ? O3 C4 C3 135.77(19) . . ? C1 C4 C3 88.20(16) . . ? N1 C5 C6 120.11(18) . . ? N1 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C7 119.90(18) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C13 C7 C6 118.32(18) . . ? C13 C7 C8 122.94(16) . . ? C6 C7 C8 118.58(16) . . ? O5 C8 C9 120.58(18) . . ? O5 C8 C7 117.46(16) . . ? C9 C8 C7 121.96(15) . . ? C10 C9 C16 119.13(18) . . ? C10 C9 C8 117.83(17) . . ? C16 C9 C8 122.99(17) . . ? C9 C10 C11 120.5(2) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 120.0(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C15 C12 C11 120.3(2) . . ? C15 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C7 119.51(17) . . ? C14 C13 H13 120.2 . . ? C7 C13 H13 120.2 . . ? N1 C14 C13 120.53(18) . . ? N1 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C12 C15 C16 120.2(2) . . ? C12 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C9 119.96(19) . . ? C15 C16 H16 120.0 . . ? C9 C16 H16 120.0 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.179 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.040 _atom_sites_special_details ; The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual = -1, Ralpha = 0.032 ; # Attachment '- Struct-133.txt' data_bi133 _database_code_depnum_ccdc_archive 'CCDC 775455' #TrackingRef '- Struct-133.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Univ.Prof. Dr. Dr. h.c. Michael Spiteller' 'Institut fur Umweltforschung (INFU)' 'Technische Universitat Dortmund' '44227 Dortmund' 'Otto-Hahn-Str. 6' 'Tel: +49 231 755 4080' 'Fax: +49 231 755 4085' 'E-mail: spiteller@infu.uni-dortmund.de' 'Hompage INFU: http://www.infu.tu-dortmund.de/' 'Dr. Bojidarka Ivanova' 'Institut fur Umweltforschung (INFU)' 'Technische Universitat Dortmund (TU Dortmund)' '44227 Dortmund' 'Otto-Hahn-Str. 6' 'Tel: +49 231 755 4089' 'Fax: +49 231 755 4085' 'E-mail: B.Ivanova@infu.uni-dortmund.de' 'Hompage INFU: http://www.infu.tu-dortmund.de/' ; _chemical_name_common ; 'Univ.Prof. Dr. Dr. h.c. Michael Spiteller' 'Institut fur Umweltforschung (INFU)' 'Technische Universitat Dortmund' '44227 Dortmund' 'Otto-Hahn-Str. 6' 'Tel ; _chemical_melting_point ? _chemical_formula_moiety 'C6 H15 N2 O, C8 H6 O3' _chemical_formula_sum 'C14 H21 N2 O4' _chemical_formula_weight 281.33 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/n' _symmetry_space_group_name_Hall '-P 2yn' 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 11.024(4) _cell_length_b 9.290(3) _cell_length_c 29.254(11) _cell_angle_alpha 90.00 _cell_angle_beta 98.054(12) _cell_angle_gamma 90.00 _cell_volume 2966.4(19) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 5315 _cell_measurement_theta_min 1.90 _cell_measurement_theta_max 25.56 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9712 _exptl_absorpt_correction_T_max 0.9844 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'micro-focus sealed tube' _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_measurement_device_type 'Bruker SMART X2S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17504 _diffrn_reflns_av_R_equivalents 0.0879 _diffrn_reflns_av_sigmaI/netI 0.1024 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.56 _reflns_number_total 5315 _reflns_number_gt 3251 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker GIS' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker APEX2' _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^)+(0.1545P)^2^+11.3751P] 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 5315 _refine_ls_number_parameters 363 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1476 _refine_ls_R_factor_gt 0.0935 _refine_ls_wR_factor_ref 0.2981 _refine_ls_wR_factor_gt 0.2603 _refine_ls_goodness_of_fit_ref 0.891 _refine_ls_restrained_S_all 0.891 _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 0.4390(3) 0.9696(4) 0.23439(12) 0.0329(8) Uani 1 1 d . . . O2 O 0.2401(3) 0.9372(4) 0.23600(15) 0.0446(10) Uani 1 1 d . . . O3 O 0.2404(3) 0.6667(4) 0.20912(13) 0.0373(9) Uani 1 1 d . . . O4 O 0.6349(4) -0.0990(5) 0.47715(14) 0.0558(11) Uani 1 1 d . . . O5 O 0.3997(5) 0.1804(7) 0.02354(16) 0.0789(16) Uani 1 1 d . . . N1 N 0.4538(4) 0.2709(4) 0.24318(14) 0.0319(10) Uani 1 1 d . . . H1 H 0.3844 0.3139 0.2500 0.048 Uiso 1 1 calc R . . H2 H 0.5192 0.3021 0.2631 0.048 Uiso 1 1 calc R . . H3 H 0.4467 0.1737 0.2457 0.048 Uiso 1 1 calc R . . C22 C 0.4507(6) 0.4615(7) 0.3914(2) 0.0526(16) Uani 1 1 d . . . H4 H 0.3717 0.4689 0.3738 0.063 Uiso 1 1 calc R . . O8 O 0.6597(3) 0.4120(4) 0.28580(12) 0.0342(9) Uani 1 1 d . . . O6 O 0.5096(3) 0.7205(4) 0.32522(12) 0.0367(9) Uani 1 1 d . . . O7 O 0.7288(3) 0.6348(4) 0.29921(14) 0.0408(9) Uani 1 1 d . . . C25 C 0.3963(4) 0.7383(5) 0.16416(17) 0.0294(11) Uani 1 1 d . . . C26 C 0.5192(5) 0.7623(6) 0.1593(2) 0.0403(13) Uani 1 1 d . . . H5 H 0.5775 0.7802 0.1858 0.048 Uiso 1 1 calc R . . C27 C 0.4714(7) 0.7371(7) 0.0772(2) 0.0578(18) Uani 1 1 d . . . H6 H 0.4971 0.7367 0.0476 0.069 Uiso 1 1 calc R . . C28 C 0.3134(5) 0.7150(6) 0.12476(19) 0.0420(13) Uani 1 1 d . . . H7 H 0.2295 0.6987 0.1273 0.050 Uiso 1 1 calc R . . N2 N 0.6202(4) -0.0449(4) 0.37997(13) 0.0299(10) Uani 1 1 d . . . N3 N 0.6751(3) -0.0822(4) 0.27727(14) 0.0292(9) Uani 1 1 d . . . H8 H 0.6816 -0.1653 0.2939 0.044 Uiso 1 1 calc R . . H9 H 0.7287 -0.0841 0.2563 0.044 Uiso 1 1 calc R . . H10 H 0.5974 -0.0733 0.2623 0.044 Uiso 1 1 calc R . . N4 N 0.3971(5) 0.2675(6) 0.11505(16) 0.0562(15) Uani 1 1 d . . . C23 C 0.3494(7) 0.3164(9) 0.0352(2) 0.068(2) Uani 1 1 d . . . H11 H 0.2806 0.3426 0.0111 0.081 Uiso 1 1 calc R . . H12 H 0.4130 0.3918 0.0357 0.081 Uiso 1 1 calc R . . C24 C 0.3055(7) 0.3124(8) 0.0799(2) 0.067(2) Uani 1 1 d . . . H13 H 0.2769 0.4096 0.0874 0.081 Uiso 1 1 calc R . . H14 H 0.2350 0.2458 0.0783 0.081 Uiso 1 1 calc R . . C1 C 0.3437(4) 0.8946(5) 0.22841(16) 0.0282(11) Uani 1 1 d . . . C2 C 0.3532(4) 0.7395(5) 0.21084(17) 0.0267(10) Uani 1 1 d . . . H15 H 0.4153 0.6873 0.2330 0.032 Uiso 1 1 calc R . . C3 C 0.5557(6) 0.7601(6) 0.1164(3) 0.0573(19) Uani 1 1 d . . . H16 H 0.6396 0.7744 0.1135 0.069 Uiso 1 1 calc R . . C4 C 0.3520(7) 0.7153(7) 0.0816(2) 0.0580(17) Uani 1 1 d . . . H17 H 0.2941 0.7000 0.0548 0.070 Uiso 1 1 calc R . . C5 C 0.7343(6) -0.1274(8) 0.4530(2) 0.0512(16) Uani 1 1 d . . . H18 H 0.7302 -0.2287 0.4424 0.061 Uiso 1 1 calc R . . H19 H 0.8119 -0.1145 0.4741 0.061 Uiso 1 1 calc R . . C6 C 0.7342(5) -0.0297(6) 0.41188(17) 0.0376(12) Uani 1 1 d . . . H20 H 0.7435 0.0714 0.4225 0.045 Uiso 1 1 calc R . . H21 H 0.8046 -0.0538 0.3957 0.045 Uiso 1 1 calc R . . C7 C 0.6130(5) 0.0623(6) 0.34237(18) 0.0365(12) Uani 1 1 d . . . H22 H 0.6256 0.1592 0.3563 0.044 Uiso 1 1 calc R . . H23 H 0.5292 0.0599 0.3250 0.044 Uiso 1 1 calc R . . C8 C 0.7036(5) 0.0416(6) 0.30873(18) 0.0339(12) Uani 1 1 d . . . H24 H 0.7057 0.1302 0.2901 0.041 Uiso 1 1 calc R . . H25 H 0.7862 0.0278 0.3263 0.041 Uiso 1 1 calc R . . C9 C 0.5155(5) -0.0207(6) 0.40561(19) 0.0416(14) Uani 1 1 d . . . H26 H 0.4379 -0.0390 0.3850 0.050 Uiso 1 1 calc R . . H27 H 0.5153 0.0808 0.4159 0.050 Uiso 1 1 calc R . . C10 C 0.5240(6) -0.1194(7) 0.4471(2) 0.0506(16) Uani 1 1 d . . . H28 H 0.4540 -0.1005 0.4641 0.061 Uiso 1 1 calc R . . H29 H 0.5185 -0.2207 0.4365 0.061 Uiso 1 1 calc R . . C11 C 0.4849(8) 0.1327(9) 0.0577(3) 0.076(2) Uani 1 1 d . . . H30 H 0.5583 0.1948 0.0591 0.092 Uiso 1 1 calc R . . H31 H 0.5094 0.0341 0.0500 0.092 Uiso 1 1 calc R . . C12 C 0.4454(6) 0.1297(6) 0.1043(2) 0.0494(15) Uani 1 1 d . . . H32 H 0.3817 0.0549 0.1051 0.059 Uiso 1 1 calc R . . H33 H 0.5160 0.1048 0.1277 0.059 Uiso 1 1 calc R . . C13 C 0.3618(5) 0.2710(8) 0.1612(2) 0.0533(16) Uani 1 1 d . . . H34 H 0.3294 0.1759 0.1688 0.064 Uiso 1 1 calc R . . H35 H 0.2967 0.3437 0.1625 0.064 Uiso 1 1 calc R . . C14 C 0.4718(5) 0.3082(6) 0.1952(2) 0.0433(14) Uani 1 1 d . . . H36 H 0.5439 0.2556 0.1870 0.052 Uiso 1 1 calc R . . H37 H 0.4885 0.4125 0.1933 0.052 Uiso 1 1 calc R . . C15 C 0.5749(7) 0.3960(7) 0.4611(2) 0.0611(19) Uani 1 1 d . . . H38 H 0.5821 0.3582 0.4915 0.073 Uiso 1 1 calc R . . C16 C 0.4626(7) 0.4080(8) 0.4355(2) 0.066(2) Uani 1 1 d . . . H39 H 0.3918 0.3792 0.4482 0.079 Uiso 1 1 calc R . . C17 C 0.5527(4) 0.5048(5) 0.37233(17) 0.0299(11) Uani 1 1 d . . . C18 C 0.5387(4) 0.5700(5) 0.32512(17) 0.0293(11) Uani 1 1 d . . . H40 H 0.4677 0.5207 0.3065 0.035 Uiso 1 1 calc R . . C19 C 0.6520(4) 0.5391(5) 0.30117(16) 0.0276(11) Uani 1 1 d . . . C20 C 0.6791(6) 0.4388(8) 0.4431(2) 0.0566(17) Uani 1 1 d . . . H41 H 0.7577 0.4311 0.4609 0.068 Uiso 1 1 calc R . . C21 C 0.6665(5) 0.4924(7) 0.3989(2) 0.0454(14) Uani 1 1 d . . . H42 H 0.7375 0.5217 0.3863 0.054 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 0.0283(18) 0.0283(19) 0.042(2) -0.0020(16) 0.0034(15) -0.0045(14) O2 0.0307(19) 0.032(2) 0.072(3) -0.0161(19) 0.0103(18) -0.0014(15) O3 0.041(2) 0.0284(19) 0.044(2) -0.0002(16) 0.0133(17) -0.0089(15) O4 0.068(3) 0.068(3) 0.033(2) -0.003(2) 0.012(2) -0.007(2) O5 0.092(4) 0.102(4) 0.042(3) -0.007(3) 0.009(3) 0.023(3) N1 0.033(2) 0.027(2) 0.035(2) -0.0004(19) 0.0043(18) -0.0011(18) C22 0.047(3) 0.061(4) 0.052(4) -0.004(3) 0.016(3) -0.010(3) O8 0.0356(19) 0.030(2) 0.040(2) -0.0110(17) 0.0138(16) -0.0044(15) O6 0.041(2) 0.028(2) 0.041(2) -0.0008(16) 0.0067(16) 0.0081(15) O7 0.039(2) 0.027(2) 0.059(3) 0.0017(18) 0.0149(18) -0.0044(16) C25 0.039(3) 0.016(2) 0.034(3) 0.002(2) 0.006(2) 0.002(2) C26 0.040(3) 0.032(3) 0.052(3) -0.007(3) 0.016(3) 0.007(2) C27 0.091(5) 0.045(4) 0.044(4) -0.001(3) 0.032(4) 0.005(3) C28 0.042(3) 0.048(3) 0.036(3) -0.008(3) 0.007(2) -0.002(3) N2 0.034(2) 0.030(2) 0.026(2) -0.0057(18) 0.0061(17) 0.0010(17) N3 0.026(2) 0.031(2) 0.031(2) 0.0013(18) 0.0045(17) -0.0039(17) N4 0.073(4) 0.064(4) 0.031(3) 0.000(3) 0.005(2) 0.027(3) C23 0.085(5) 0.075(5) 0.043(4) 0.027(4) 0.009(4) 0.017(4) C24 0.083(5) 0.063(5) 0.056(4) 0.015(4) 0.008(4) 0.026(4) C1 0.032(3) 0.026(3) 0.026(3) -0.001(2) 0.004(2) 0.003(2) C2 0.032(2) 0.013(2) 0.034(3) 0.000(2) 0.002(2) 0.0008(18) C3 0.067(4) 0.034(3) 0.082(5) -0.005(3) 0.047(4) 0.005(3) C4 0.087(5) 0.054(4) 0.034(3) -0.002(3) 0.012(3) 0.003(4) C5 0.053(4) 0.064(4) 0.034(3) -0.001(3) -0.001(3) -0.001(3) C6 0.043(3) 0.039(3) 0.030(3) -0.002(2) 0.002(2) -0.002(2) C7 0.052(3) 0.023(3) 0.035(3) -0.001(2) 0.009(2) 0.006(2) C8 0.037(3) 0.028(3) 0.037(3) 0.001(2) 0.004(2) -0.007(2) C9 0.045(3) 0.042(3) 0.042(3) -0.012(3) 0.019(3) 0.000(2) C10 0.062(4) 0.052(4) 0.043(3) -0.006(3) 0.026(3) -0.012(3) C11 0.103(6) 0.066(5) 0.064(5) 0.000(4) 0.026(5) 0.025(4) C12 0.065(4) 0.038(3) 0.045(3) 0.004(3) 0.006(3) 0.012(3) C13 0.046(3) 0.071(4) 0.043(3) 0.002(3) 0.007(3) 0.006(3) C14 0.045(3) 0.040(3) 0.045(3) 0.008(3) 0.009(3) -0.004(3) C15 0.099(6) 0.050(4) 0.038(4) 0.008(3) 0.019(4) 0.000(4) C16 0.079(5) 0.074(5) 0.053(4) 0.004(4) 0.036(4) -0.014(4) C17 0.038(3) 0.021(2) 0.032(3) -0.007(2) 0.009(2) 0.000(2) C18 0.032(2) 0.023(3) 0.032(3) -0.005(2) 0.002(2) -0.002(2) C19 0.032(3) 0.026(3) 0.024(2) -0.002(2) 0.002(2) -0.002(2) C20 0.062(4) 0.071(5) 0.034(3) 0.012(3) 0.000(3) 0.008(3) C21 0.043(3) 0.048(4) 0.046(3) 0.002(3) 0.009(3) -0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.253(6) . ? O2 C1 1.257(6) . ? O3 C2 1.410(6) . ? O4 C5 1.409(7) . ? O4 C10 1.415(8) . ? O5 C11 1.348(9) . ? O5 C23 1.440(9) . ? N1 C14 1.487(7) . ? N1 H1 0.9100 . ? N1 H2 0.9100 . ? N1 H3 0.9100 . ? C22 C16 1.370(9) . ? C22 C17 1.384(7) . ? C22 H4 0.9500 . ? O8 C19 1.270(6) . ? O6 C18 1.435(6) . ? O7 C19 1.235(6) . ? C25 C28 1.384(7) . ? C25 C26 1.400(7) . ? C25 C2 1.507(7) . ? C26 C3 1.371(8) . ? C26 H5 0.9500 . ? C27 C4 1.355(10) . ? C27 C3 1.387(10) . ? C27 H6 0.9500 . ? C28 C4 1.387(8) . ? C28 H7 0.9500 . ? N2 C6 1.464(6) . ? N2 C7 1.478(7) . ? N2 C9 1.479(6) . ? N3 C8 1.479(6) . ? N3 H8 0.9100 . ? N3 H9 0.9100 . ? N3 H10 0.9100 . ? N4 C24 1.399(8) . ? N4 C12 1.438(8) . ? N4 C13 1.457(8) . ? C23 C24 1.458(9) . ? C23 H11 0.9900 . ? C23 H12 0.9900 . ? C24 H13 0.9900 . ? C24 H14 0.9900 . ? C1 C2 1.538(6) . ? C2 H15 1.0000 . ? C3 H16 0.9500 . ? C4 H17 0.9500 . ? C5 C6 1.507(8) . ? C5 H18 0.9900 . ? C5 H19 0.9900 . ? C6 H20 0.9900 . ? C6 H21 0.9900 . ? C7 C8 1.510(7) . ? C7 H22 0.9900 . ? C7 H23 0.9900 . ? C8 H24 0.9900 . ? C8 H25 0.9900 . ? C9 C10 1.514(8) . ? C9 H26 0.9900 . ? C9 H27 0.9900 . ? C10 H28 0.9900 . ? C10 H29 0.9900 . ? C11 C12 1.486(9) . ? C11 H30 0.9900 . ? C11 H31 0.9900 . ? C12 H32 0.9900 . ? C12 H33 0.9900 . ? C13 C14 1.496(8) . ? C13 H34 0.9900 . ? C13 H35 0.9900 . ? C14 H36 0.9900 . ? C14 H37 0.9900 . ? C15 C16 1.359(10) . ? C15 C20 1.387(9) . ? C15 H38 0.9500 . ? C16 H39 0.9500 . ? C17 C21 1.385(7) . ? C17 C18 1.496(7) . ? C18 C19 1.542(6) . ? C18 H40 1.0000 . ? C20 C21 1.373(8) . ? C20 H41 0.9500 . ? C21 H42 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O4 C10 109.2(4) . . ? C11 O5 C23 111.4(6) . . ? C14 N1 H1 109.5 . . ? C14 N1 H2 109.5 . . ? H1 N1 H2 109.5 . . ? C14 N1 H3 109.5 . . ? H1 N1 H3 109.5 . . ? H2 N1 H3 109.5 . . ? C16 C22 C17 120.6(6) . . ? C16 C22 H4 119.7 . . ? C17 C22 H4 119.7 . . ? C28 C25 C26 118.5(5) . . ? C28 C25 C2 120.0(4) . . ? C26 C25 C2 121.5(5) . . ? C3 C26 C25 120.2(6) . . ? C3 C26 H5 119.9 . . ? C25 C26 H5 119.9 . . ? C4 C27 C3 119.5(6) . . ? C4 C27 H6 120.3 . . ? C3 C27 H6 120.3 . . ? C25 C28 C4 120.4(5) . . ? C25 C28 H7 119.8 . . ? C4 C28 H7 119.8 . . ? C6 N2 C7 111.2(4) . . ? C6 N2 C9 108.8(4) . . ? C7 N2 C9 108.1(4) . . ? C8 N3 H8 109.5 . . ? C8 N3 H9 109.5 . . ? H8 N3 H9 109.5 . . ? C8 N3 H10 109.5 . . ? H8 N3 H10 109.5 . . ? H9 N3 H10 109.5 . . ? C24 N4 C12 110.8(5) . . ? C24 N4 C13 114.5(5) . . ? C12 N4 C13 112.2(5) . . ? O5 C23 C24 112.2(6) . . ? O5 C23 H11 109.2 . . ? C24 C23 H11 109.2 . . ? O5 C23 H12 109.2 . . ? C24 C23 H12 109.2 . . ? H11 C23 H12 107.9 . . ? N4 C24 C23 111.8(6) . . ? N4 C24 H13 109.3 . . ? C23 C24 H13 109.3 . . ? N4 C24 H14 109.3 . . ? C23 C24 H14 109.3 . . ? H13 C24 H14 107.9 . . ? O1 C1 O2 124.4(5) . . ? O1 C1 C2 118.2(4) . . ? O2 C1 C2 117.4(4) . . ? O3 C2 C25 110.6(4) . . ? O3 C2 C1 111.1(4) . . ? C25 C2 C1 110.8(4) . . ? O3 C2 H15 108.1 . . ? C25 C2 H15 108.1 . . ? C1 C2 H15 108.1 . . ? C26 C3 C27 120.7(6) . . ? C26 C3 H16 119.7 . . ? C27 C3 H16 119.7 . . ? C27 C4 C28 120.8(6) . . ? C27 C4 H17 119.6 . . ? C28 C4 H17 119.6 . . ? O4 C5 C6 112.0(5) . . ? O4 C5 H18 109.2 . . ? C6 C5 H18 109.2 . . ? O4 C5 H19 109.2 . . ? C6 C5 H19 109.2 . . ? H18 C5 H19 107.9 . . ? N2 C6 C5 110.8(4) . . ? N2 C6 H20 109.5 . . ? C5 C6 H20 109.5 . . ? N2 C6 H21 109.5 . . ? C5 C6 H21 109.5 . . ? H20 C6 H21 108.1 . . ? N2 C7 C8 115.3(4) . . ? N2 C7 H22 108.4 . . ? C8 C7 H22 108.4 . . ? N2 C7 H23 108.4 . . ? C8 C7 H23 108.4 . . ? H22 C7 H23 107.5 . . ? N3 C8 C7 113.7(4) . . ? N3 C8 H24 108.8 . . ? C7 C8 H24 108.8 . . ? N3 C8 H25 108.8 . . ? C7 C8 H25 108.8 . . ? H24 C8 H25 107.7 . . ? N2 C9 C10 110.5(5) . . ? N2 C9 H26 109.6 . . ? C10 C9 H26 109.6 . . ? N2 C9 H27 109.6 . . ? C10 C9 H27 109.6 . . ? H26 C9 H27 108.1 . . ? O4 C10 C9 111.6(5) . . ? O4 C10 H28 109.3 . . ? C9 C10 H28 109.3 . . ? O4 C10 H29 109.3 . . ? C9 C10 H29 109.3 . . ? H28 C10 H29 108.0 . . ? O5 C11 C12 115.0(6) . . ? O5 C11 H30 108.5 . . ? C12 C11 H30 108.5 . . ? O5 C11 H31 108.5 . . ? C12 C11 H31 108.5 . . ? H30 C11 H31 107.5 . . ? N4 C12 C11 110.5(5) . . ? N4 C12 H32 109.6 . . ? C11 C12 H32 109.6 . . ? N4 C12 H33 109.6 . . ? C11 C12 H33 109.6 . . ? H32 C12 H33 108.1 . . ? N4 C13 C14 108.9(5) . . ? N4 C13 H34 109.9 . . ? C14 C13 H34 109.9 . . ? N4 C13 H35 109.9 . . ? C14 C13 H35 109.9 . . ? H34 C13 H35 108.3 . . ? N1 C14 C13 111.8(4) . . ? N1 C14 H36 109.3 . . ? C13 C14 H36 109.3 . . ? N1 C14 H37 109.3 . . ? C13 C14 H37 109.3 . . ? H36 C14 H37 107.9 . . ? C16 C15 C20 120.4(6) . . ? C16 C15 H38 119.8 . . ? C20 C15 H38 119.8 . . ? C15 C16 C22 120.5(6) . . ? C15 C16 H39 119.7 . . ? C22 C16 H39 119.7 . . ? C22 C17 C21 118.2(5) . . ? C22 C17 C18 120.4(5) . . ? C21 C17 C18 121.3(4) . . ? O6 C18 C17 112.7(4) . . ? O6 C18 C19 112.2(4) . . ? C17 C18 C19 111.0(4) . . ? O6 C18 H40 106.8 . . ? C17 C18 H40 106.8 . . ? C19 C18 H40 106.8 . . ? O7 C19 O8 125.0(4) . . ? O7 C19 C18 119.4(4) . . ? O8 C19 C18 115.6(4) . . ? C21 C20 C15 118.8(6) . . ? C21 C20 H41 120.6 . . ? C15 C20 H41 120.6 . . ? C20 C21 C17 121.5(5) . . ? C20 C21 H42 119.3 . . ? C17 C21 H42 119.3 . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 25.56 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.553 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.077 # Attachment '- Struct-200-10.txt' data_200-10 _database_code_depnum_ccdc_archive 'CCDC 792093' #TrackingRef '- Struct-200-10.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Univ.Prof. Dr. Dr. h.c. Michael Spiteller' 'Institut fur Umweltforschung (INFU)' 'Technische Universitat Dortmund' '44227 Dortmund' 'Otto-Hahn-Str. 6' 'Tel: +49 231 755 4080' 'Fax: +49 231 755 4085' 'E-mail: spiteller@infu.uni-dortmund.de' 'Hompage INFU: http://www.infu.tu-dortmund.de/' 'Dr. Bojidarka Ivanova' 'Institut fur Umweltforschung (INFU)' 'Technische Universitat Dortmund (TU Dortmund)' '44227 Dortmund' 'Otto-Hahn-Str. 6' 'Tel: +49 231 755 4089' 'Fax: +49 231 755 4085' 'E-mail: B.Ivanova@infu.uni-dortmund.de' 'Hompage INFU: http://www.infu.tu-dortmund.de/' ; _chemical_name_common ; 'Univ.Prof. Dr. Dr. h.c. Michael Spiteller' 'Institut fur Umweltforschung (INFU)' 'Technische Universitat Dortmund' '44227 Dortmund' 'Otto-Hahn-Str. 6' 'Tel ; _chemical_melting_point 344K _chemical_formula_moiety 'C8 H19 N2 O2, C8 H8 O3, C8 H7 O3' _chemical_formula_sum 'C24 H34 Cl0 N2 O8' _chemical_formula_weight 478.53 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' Cl Cl 0.1484 0.1585 '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 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.711(3) _cell_length_b 12.974(6) _cell_length_c 23.865(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2387.3(19) _cell_formula_units_Z 4 _cell_measurement_temperature 199(2) _cell_measurement_reflns_used 1935 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 19.21 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9880 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 199(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'micro-focus sealed tube' _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_measurement_device_type 'Bruker SMART X2S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12494 _diffrn_reflns_av_R_equivalents 0.18 _diffrn_reflns_av_sigmaI/netI 0.1904 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 19.21 _reflns_number_total 1935 _reflns_number_gt 1484 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker GIS' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker APEX2' _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^)+(0.1000P)^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 0.000(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(5) _refine_ls_number_reflns 1935 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1227 _refine_ls_R_factor_gt 0.1047 _refine_ls_wR_factor_ref 0.2338 _refine_ls_wR_factor_gt 0.2195 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.003 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 C20 C 0.1582(11) 0.6808(7) 0.5784(4) 0.037(3) Uani 1 1 d . . . H1 H 0.2083 0.7249 0.6082 0.045 Uiso 1 1 calc R . . H2 H 0.1124 0.7264 0.5487 0.045 Uiso 1 1 calc R . . N1 N 0.3644(9) 0.5381(6) 0.5972(3) 0.036(2) Uani 1 1 d . . . N2 N 0.0134(9) 0.6187(6) 0.6024(3) 0.033(2) Uani 1 1 d . . . H3 H -0.0349 0.5805 0.5733 0.039 Uiso 1 1 calc R . . O5 O 1.4227(8) 0.0134(6) 0.4816(3) 0.050(2) Uani 1 1 d . . . C16 C 1.3747(13) 0.0400(8) 0.5797(4) 0.044(3) Uani 1 1 d . . . H4 H 1.4595 0.0983 0.5791 0.053 Uiso 1 1 calc R . . O1 O 1.4031(11) -0.0198(6) 0.6292(3) 0.069(2) Uani 1 1 d . . . H5 H 1.4104 -0.0824 0.6206 0.103 Uiso 1 1 calc R . . C15 C 0.2179(13) 0.4775(8) 0.6205(4) 0.040(3) Uani 1 1 d . . . H6 H 0.1662 0.4351 0.5903 0.048 Uiso 1 1 calc R . . H7 H 0.2621 0.4304 0.6498 0.048 Uiso 1 1 calc R . . C14 C 0.0831(12) 0.5444(7) 0.6447(4) 0.038(3) Uani 1 1 d . . . H8 H 0.1325 0.5832 0.6767 0.045 Uiso 1 1 calc R . . H9 H -0.0129 0.5012 0.6591 0.045 Uiso 1 1 calc R . . C13 C 0.2986(12) 0.6131(8) 0.5543(4) 0.042(3) Uani 1 1 d . . . H10 H 0.2521 0.5747 0.5217 0.051 Uiso 1 1 calc R . . H11 H 0.3957 0.6566 0.5410 0.051 Uiso 1 1 calc R . . C12 C 0.995(2) 0.2184(9) 0.5549(4) 0.068(4) Uani 1 1 d . . . H12 H 0.9752 0.2866 0.5419 0.082 Uiso 1 1 calc R . . C9 C 1.1932(14) 0.0834(9) 0.5769(4) 0.040(3) Uani 1 1 d . . . C8 C 0.8848(16) 0.0598(10) 0.5896(5) 0.061(3) Uani 1 1 d . . . H13 H 0.7896 0.0180 0.6006 0.074 Uiso 1 1 calc R . . C6 C 1.1647(14) 0.1804(10) 0.5581(4) 0.050(3) Uani 1 1 d . . . H14 H 1.2595 0.2225 0.5471 0.060 Uiso 1 1 calc R . . C2 C 1.0527(16) 0.0220(9) 0.5928(4) 0.053(3) Uani 1 1 d . . . H15 H 1.0724 -0.0461 0.6060 0.064 Uiso 1 1 calc R . . C1 C 0.8578(16) 0.1576(11) 0.5705(5) 0.068(4) Uani 1 1 d . . . H16 H 0.7430 0.1838 0.5679 0.081 Uiso 1 1 calc R . . O4 O -0.2973(9) 0.6997(6) 0.5425(3) 0.055(2) Uani 1 1 d . . . H17 H -0.2211 0.6720 0.5224 0.082 Uiso 1 1 calc R . . O3 O 1.4110(10) -0.1241(7) 0.5370(3) 0.061(2) Uani 1 1 d . . . C25 C 1.4076(12) -0.0295(12) 0.5284(5) 0.045(3) Uani 1 1 d . . . C23 C -0.2181(14) 0.7534(8) 0.5859(4) 0.047(3) Uani 1 1 d . . . H18 H -0.3069 0.7942 0.6060 0.056 Uiso 1 1 calc R . . H19 H -0.1327 0.8022 0.5699 0.056 Uiso 1 1 calc R . . C22 C 0.5017(13) 0.4734(8) 0.5706(4) 0.048(3) Uani 1 1 d . . . H20 H 0.5913 0.5194 0.5546 0.057 Uiso 1 1 calc R . . H21 H 0.4492 0.4343 0.5393 0.057 Uiso 1 1 calc R . . O2 O 0.6861(10) 0.4525(7) 0.6522(4) 0.082(3) Uani 1 1 d . . . H22 H 0.6227 0.4980 0.6666 0.123 Uiso 1 1 calc R . . C26 C -0.1274(13) 0.6840(8) 0.6270(4) 0.040(3) Uani 1 1 d . . . H23 H -0.0768 0.7271 0.6571 0.048 Uiso 1 1 calc R . . H24 H -0.2146 0.6382 0.6445 0.048 Uiso 1 1 calc R . . C18 C 0.2207(17) 0.6376(11) 0.2679(4) 0.056(3) Uani 1 1 d . . . H25 H 0.1236 0.6033 0.2838 0.067 Uiso 1 1 calc R . . C19 C 0.0186(15) 0.7757(9) 0.2339(4) 0.051(3) Uani 1 1 d . . . H26 H -0.0693 0.7196 0.2385 0.061 Uiso 1 1 calc R . . C29 C 0.386(2) 0.5940(10) 0.2729(5) 0.069(4) Uani 1 1 d . . . H27 H 0.3999 0.5296 0.2913 0.083 Uiso 1 1 calc R . . C27 C 0.5061(18) 0.7331(14) 0.2234(5) 0.078(4) Uani 1 1 d . . . H28 H 0.6047 0.7664 0.2078 0.094 Uiso 1 1 calc R . . O6 O -0.0364(11) 0.8220(6) 0.3298(3) 0.063(2) Uani 1 1 d . . . H29 H -0.0470 0.7577 0.3277 0.095 Uiso 1 1 calc R . . C28 C 0.1970(15) 0.7299(10) 0.2402(4) 0.043(3) Uani 1 1 d . . . C30 C 0.526(2) 0.6431(14) 0.2516(6) 0.076(4) Uani 1 1 d . . . H30 H 0.6385 0.6146 0.2565 0.091 Uiso 1 1 calc R . . O7 O 0.0047(14) 0.9470(8) 0.2697(3) 0.095(3) Uani 1 1 d . . . O8 O -0.0074(13) 0.8232(6) 0.1826(3) 0.074(3) Uani 1 1 d . . . H31 H 0.0066 0.8871 0.1861 0.111 Uiso 1 1 calc R . . C31 C -0.0091(14) 0.8581(13) 0.2818(5) 0.060(3) Uani 1 1 d . . . C32 C 0.3404(17) 0.7777(10) 0.2170(4) 0.061(3) Uani 1 1 d . . . H32 H 0.3274 0.8403 0.1968 0.073 Uiso 1 1 calc R . . C33 C 0.5898(16) 0.3971(9) 0.6106(5) 0.068(4) Uani 1 1 d . . . H33 H 0.5010 0.3536 0.6290 0.081 Uiso 1 1 calc R . . H34 H 0.6687 0.3515 0.5892 0.081 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C20 0.027(6) 0.037(6) 0.048(6) 0.011(6) -0.001(5) -0.003(6) N1 0.031(5) 0.038(5) 0.039(5) 0.007(4) 0.002(4) 0.004(5) N2 0.028(5) 0.038(5) 0.032(4) 0.000(4) -0.006(4) -0.001(5) O5 0.048(5) 0.066(5) 0.038(4) -0.006(4) 0.009(3) 0.008(4) C16 0.037(7) 0.063(7) 0.033(7) 0.003(6) -0.002(5) 0.005(6) O1 0.076(6) 0.090(6) 0.041(4) 0.000(5) -0.015(4) 0.015(6) C15 0.037(7) 0.039(7) 0.043(6) 0.011(6) -0.002(5) 0.008(6) C14 0.042(7) 0.043(6) 0.028(5) 0.017(6) -0.006(5) -0.007(6) C13 0.038(6) 0.053(7) 0.035(5) 0.008(6) 0.000(5) 0.001(6) C12 0.085(12) 0.048(8) 0.071(7) -0.018(7) -0.019(8) 0.015(9) C9 0.048(9) 0.032(7) 0.040(6) -0.004(6) 0.012(6) 0.003(7) C8 0.042(9) 0.058(9) 0.084(9) 0.001(7) 0.018(6) 0.005(7) C6 0.039(9) 0.058(9) 0.054(7) 0.005(6) 0.005(5) -0.007(7) C2 0.050(8) 0.054(7) 0.056(6) -0.003(6) 0.007(6) 0.005(8) C1 0.036(8) 0.065(10) 0.103(10) -0.007(8) 0.013(7) 0.008(8) O4 0.040(4) 0.068(6) 0.056(5) -0.003(4) -0.012(4) 0.008(4) O3 0.070(6) 0.062(6) 0.050(5) 0.002(5) -0.007(4) 0.016(5) C25 0.022(6) 0.075(10) 0.038(8) -0.010(8) -0.002(5) 0.006(6) C23 0.048(7) 0.043(7) 0.050(6) -0.007(6) 0.016(6) 0.002(6) C22 0.033(6) 0.055(7) 0.055(6) -0.009(6) -0.003(6) 0.007(6) O2 0.057(5) 0.088(7) 0.101(7) 0.009(6) -0.021(5) 0.010(5) C26 0.039(6) 0.048(7) 0.034(5) 0.001(6) -0.005(5) 0.009(6) C18 0.059(10) 0.072(10) 0.038(6) -0.009(7) -0.002(6) -0.005(8) C19 0.061(9) 0.070(8) 0.021(6) -0.006(6) 0.004(6) 0.000(7) C29 0.087(12) 0.060(8) 0.062(9) -0.018(7) -0.015(9) 0.009(10) C27 0.044(10) 0.130(14) 0.060(8) -0.021(9) 0.020(7) -0.004(10) O6 0.051(5) 0.080(6) 0.059(5) -0.009(5) 0.004(4) 0.000(5) C28 0.045(8) 0.060(8) 0.025(6) -0.004(6) 0.008(6) -0.007(7) C30 0.070(12) 0.085(11) 0.074(9) -0.021(9) -0.003(8) 0.034(10) O7 0.147(10) 0.078(7) 0.061(5) 0.012(6) 0.009(6) 0.032(7) O8 0.092(7) 0.092(6) 0.037(4) -0.002(4) -0.010(4) 0.006(6) C31 0.046(7) 0.098(11) 0.036(8) 0.025(9) -0.001(7) -0.004(8) C32 0.064(10) 0.081(9) 0.039(7) -0.002(6) 0.008(7) -0.014(9) C33 0.061(8) 0.072(9) 0.070(8) 0.001(9) -0.002(7) 0.005(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 C20 N2 1.490(11) . ? C20 C13 1.508(12) . ? N1 C15 1.484(11) . ? N1 C22 1.493(11) . ? N1 C13 1.501(11) . ? N2 C26 1.497(11) . ? N2 C14 1.497(10) . ? O5 C25 1.252(13) . ? C16 O1 1.429(11) . ? C16 C9 1.510(14) . ? C16 C25 1.542(13) . ? C15 C14 1.472(13) . ? C12 C1 1.373(17) . ? C12 C6 1.398(17) . ? C9 C6 1.354(13) . ? C9 C2 1.397(15) . ? C8 C1 1.365(15) . ? C8 C2 1.386(15) . ? O4 C23 1.389(11) . ? O3 C25 1.245(13) . ? C23 C26 1.503(13) . ? C22 C33 1.534(13) . ? O2 C33 1.433(12) . ? C18 C28 1.381(15) . ? C18 C29 1.400(17) . ? C19 O8 1.385(11) . ? C19 C28 1.505(15) . ? C19 C31 1.579(16) . ? C29 C30 1.353(18) . ? C27 C30 1.357(18) . ? C27 C32 1.411(18) . ? O6 C31 1.256(12) . ? C28 C32 1.383(15) . ? O7 C31 1.193(14) . ? 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 N2 C20 C13 111.7(8) . . ? C15 N1 C22 113.7(7) . . ? C15 N1 C13 109.9(7) . . ? C22 N1 C13 108.3(7) . . ? C20 N2 C26 112.8(7) . . ? C20 N2 C14 109.7(7) . . ? C26 N2 C14 111.1(6) . . ? O1 C16 C9 112.4(8) . . ? O1 C16 C25 108.3(9) . . ? C9 C16 C25 109.6(8) . . ? C14 C15 N1 111.9(8) . . ? C15 C14 N2 111.6(7) . . ? N1 C13 C20 111.1(7) . . ? C1 C12 C6 120.3(11) . . ? C6 C9 C2 119.6(10) . . ? C6 C9 C16 120.8(10) . . ? C2 C9 C16 119.6(10) . . ? C1 C8 C2 119.3(11) . . ? C9 C6 C12 119.8(11) . . ? C8 C2 C9 120.5(11) . . ? C8 C1 C12 120.4(11) . . ? O3 C25 O5 125.7(10) . . ? O3 C25 C16 116.6(10) . . ? O5 C25 C16 117.6(11) . . ? O4 C23 C26 113.0(8) . . ? N1 C22 C33 114.3(8) . . ? N2 C26 C23 114.8(7) . . ? C28 C18 C29 120.8(12) . . ? O8 C19 C28 113.3(9) . . ? O8 C19 C31 108.5(9) . . ? C28 C19 C31 108.6(8) . . ? C30 C29 C18 120.3(12) . . ? C30 C27 C32 120.6(13) . . ? C18 C28 C32 118.3(11) . . ? C18 C28 C19 120.7(11) . . ? C32 C28 C19 121.0(12) . . ? C29 C30 C27 120.1(13) . . ? O7 C31 O6 126.5(13) . . ? O7 C31 C19 117.9(10) . . ? O6 C31 C19 115.5(13) . . ? C28 C32 C27 119.8(12) . . ? O2 C33 C22 109.7(9) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 19.21 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.229 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.061 # Attachment '- Struct-16.txt' data_bi119 _database_code_depnum_ccdc_archive 'CCDC 793589' #TrackingRef '- Struct-16.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Univ.Prof. Dr. Dr. h.c. Michael Spiteller' 'Institut fur Umweltforschung (INFU)' 'Technische Universitat Dortmund' '44227 Dortmund' 'Otto-Hahn-Str. 6' 'Tel: +49 231 755 4080' 'Fax: +49 231 755 4085' 'E-mail: spiteller@infu.uni-dortmund.de' 'Hompage INFU: http://www.infu.tu-dortmund.de/' 'Dr. Bojidarka Ivanova' 'Institut fur Umweltforschung (INFU)' 'Technische Universitat Dortmund (TU Dortmund)' '44227 Dortmund' 'Otto-Hahn-Str. 6' 'Tel: +49 231 755 4089' 'Fax: +49 231 755 4085' 'E-mail: B.Ivanova@infu.uni-dortmund.de' 'Hompage INFU: http://www.infu.tu-dortmund.de/' ; _chemical_name_common ; 'Univ.Prof. Dr. Dr. h.c. Michael Spiteller' 'Institut fur Umweltforschung (INFU)' 'Technische Universitat Dortmund' '44227 Dortmund' 'Otto-Hahn-Str. 6' 'Tel ; _chemical_melting_point ? _chemical_formula_moiety 'C6 H7 N2 O, 0.5(C4 O4)' _chemical_formula_sum 'C8 H7 N2 O3' _chemical_formula_weight 179.16 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 'C 2/c' _symmetry_space_group_name_Hall '- C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.047(6) _cell_length_b 8.368(2) _cell_length_c 9.364(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.972(8) _cell_angle_gamma 90.00 _cell_volume 1613.2(7) _cell_formula_units_Z 8 _cell_measurement_temperature 199(2) _cell_measurement_reflns_used 1423 _cell_measurement_theta_min 1.98 _cell_measurement_theta_max 25.16 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9577 _exptl_absorpt_correction_T_max 0.9761 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 199(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'micro-focus sealed tube' _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_measurement_device_type 'Bruker SMART X2S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 4877 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.16 _reflns_number_total 1423 _reflns_number_gt 1137 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker GIS' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker APEX2' _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^)+(0.1080P)^2^+2.0956P] 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 1423 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.1220 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 0.687 _refine_ls_restrained_S_all 0.687 _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 0.79802(7) 0.62349(16) 0.78827(16) 0.0561(4) Uani 1 1 d . . . H1 H 0.8295 0.5701 0.8342 0.084 Uiso 1 1 calc R . . O2 O 1.10817(6) 0.55090(17) 1.07104(18) 0.0606(5) Uani 1 1 d . . . O3 O 1.01278(7) 0.23864(15) 1.06770(16) 0.0553(4) Uani 1 1 d . . . N1 N 0.76210(7) 0.53059(19) 0.67830(16) 0.0454(4) Uani 1 1 d . . . N2 N 0.59124(7) 0.56935(18) 0.26475(16) 0.0415(4) Uani 1 1 d . . . H2 H 0.5662 0.6330 0.2025 0.050 Uiso 1 1 calc R . . C8 C 1.00683(9) 0.3827(2) 1.03225(19) 0.0402(4) Uani 1 1 d . . . C1 C 0.71768(9) 0.6134(2) 0.59836(19) 0.0424(5) Uani 1 1 d . . . H1A H 0.7137 0.7240 0.6179 0.051 Uiso 1 1 calc R . . C2 C 0.67287(8) 0.5387(2) 0.47693(18) 0.0375(4) Uani 1 1 d . . . C3 C 0.63180(8) 0.6338(2) 0.3782(2) 0.0408(4) Uani 1 1 d . . . H3 H 0.6325 0.7464 0.3913 0.049 Uiso 1 1 calc R . . C4 C 0.58706(9) 0.4124(2) 0.2417(2) 0.0447(5) Uani 1 1 d . . . H4 H 0.5577 0.3704 0.1594 0.054 Uiso 1 1 calc R . . C5 C 0.66891(9) 0.3749(2) 0.4556(2) 0.0443(5) Uani 1 1 d . . . H5 H 0.6961 0.3058 0.5221 0.053 Uiso 1 1 calc R . . C6 C 0.62573(10) 0.3119(2) 0.3383(2) 0.0490(5) Uani 1 1 d . . . H6 H 0.6227 0.1994 0.3243 0.059 Uiso 1 1 calc R . . C7 C 1.04894(8) 0.5205(2) 1.03359(19) 0.0418(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0532(9) 0.0469(9) 0.0568(9) -0.0085(6) -0.0152(7) 0.0053(6) O2 0.0357(7) 0.0481(8) 0.0858(11) 0.0090(7) -0.0156(7) -0.0016(6) O3 0.0507(8) 0.0336(7) 0.0695(9) 0.0134(6) -0.0152(7) 0.0023(6) N1 0.0422(9) 0.0461(9) 0.0432(9) -0.0034(7) -0.0022(7) 0.0018(7) N2 0.0365(8) 0.0426(9) 0.0415(8) 0.0071(7) -0.0009(6) 0.0090(6) C8 0.0401(9) 0.0320(9) 0.0412(10) 0.0031(7) -0.0082(8) 0.0035(7) C1 0.0400(10) 0.0420(10) 0.0425(10) 0.0013(8) 0.0024(8) 0.0055(7) C2 0.0340(9) 0.0419(10) 0.0363(9) 0.0034(7) 0.0066(7) 0.0065(7) C3 0.0383(9) 0.0362(10) 0.0450(10) 0.0023(8) 0.0023(8) 0.0066(7) C4 0.0418(10) 0.0478(11) 0.0426(10) -0.0007(8) 0.0043(8) 0.0018(8) C5 0.0461(10) 0.0424(11) 0.0423(10) 0.0074(8) 0.0047(8) 0.0118(8) C6 0.0568(12) 0.0370(10) 0.0511(11) 0.0008(8) 0.0059(9) 0.0036(8) C7 0.0365(9) 0.0360(9) 0.0447(10) 0.0027(8) -0.0103(7) 0.0025(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 O1 N1 1.3832(19) . ? O1 H1 0.8400 . ? O2 C7 1.249(2) . ? O3 C8 1.250(2) . ? N1 C1 1.275(2) . ? N2 C4 1.331(2) . ? N2 C3 1.331(2) . ? N2 H2 0.8800 . ? C8 C7 1.453(3) . ? C8 C7 1.454(2) 5_767 ? C1 C2 1.459(3) . ? C1 H1A 0.9500 . ? C2 C3 1.380(2) . ? C2 C5 1.385(3) . ? C3 H3 0.9500 . ? C4 C6 1.372(3) . ? C4 H4 0.9500 . ? C5 C6 1.377(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.454(2) 5_767 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 O1 H1 109.5 . . ? C1 N1 O1 110.65(16) . . ? C4 N2 C3 122.61(15) . . ? C4 N2 H2 118.7 . . ? C3 N2 H2 118.7 . . ? O3 C8 C7 137.40(17) . . ? O3 C8 C7 132.64(17) . 5_767 ? C7 C8 C7 89.94(14) . 5_767 ? N1 C1 C2 120.10(17) . . ? N1 C1 H1A 120.0 . . ? C2 C1 H1A 120.0 . . ? C3 C2 C5 117.60(16) . . ? C3 C2 C1 119.29(17) . . ? C5 C2 C1 123.11(16) . . ? N2 C3 C2 120.67(17) . . ? N2 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? N2 C4 C6 119.21(17) . . ? N2 C4 H4 120.4 . . ? C6 C4 H4 120.4 . . ? C6 C5 C2 120.27(17) . . ? C6 C5 H5 119.9 . . ? C2 C5 H5 119.9 . . ? C4 C6 C5 119.60(19) . . ? C4 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? O2 C7 C8 137.33(16) . . ? O2 C7 C8 132.60(17) . 5_767 ? C8 C7 C8 90.06(14) . 5_767 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.16 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.156 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.035 # Attachment '- Struct-137.txt' data_bi137 _database_code_depnum_ccdc_archive 'CCDC 880481' #TrackingRef '- Struct-137.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Univ.Prof. Dr. Dr. h.c. Michael Spiteller' 'Institut fur Umweltforschung (INFU)' 'Technische Universitat Dortmund' '44227 Dortmund' 'Otto-Hahn-Str. 6' 'Tel: +49 231 755 4080' 'Fax: +49 231 755 4085' 'E-mail: spiteller@infu.uni-dortmund.de' 'Hompage INFU: http://www.infu.tu-dortmund.de/' 'Dr. Bojidarka Ivanova' 'Institut fur Umweltforschung (INFU)' 'Technische Universitat Dortmund (TU Dortmund)' '44227 Dortmund' 'Otto-Hahn-Str. 6' 'Tel: +49 231 755 4089' 'Fax: +49 231 755 4085' 'E-mail: B.Ivanova@infu.uni-dortmund.de' 'Hompage INFU: http://www.infu.tu-dortmund.de/' ; _chemical_name_common ; 'Univ.Prof. Dr. Dr. h.c. Michael Spiteller' 'Institut fur Umweltforschung (INFU)' 'Technische Universitat Dortmund' '44227 Dortmund' 'Otto-Hahn-Str. 6' 'Tel ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H8 O3' _chemical_formula_weight 152.14 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 Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 9.9537(15) _cell_length_b 9.6632(15) _cell_length_c 16.173(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1555.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used 1386 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 5.10 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.9610 _exptl_absorpt_correction_T_max 0.9796 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'micro-focus sealed tube' _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_measurement_device_type 'Bruker SMART X2S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8941 _diffrn_reflns_av_R_equivalents 0.0486 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 25.10 _reflns_number_total 1386 _reflns_number_gt 1043 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker GIS' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker APEX2' _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^)+(0.1114P)^2^+0.5456P] 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 1386 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1440 _refine_ls_wR_factor_gt 0.1244 _refine_ls_goodness_of_fit_ref 0.796 _refine_ls_restrained_S_all 0.796 _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 -0.08264(15) 0.64940(14) 0.49441(10) 0.0648(5) Uani 1 1 d . . . O2 O -0.06752(13) 0.86358(13) 0.54246(9) 0.0557(4) Uani 1 1 d . . . H2 H -0.1456 0.8694 0.5231 0.084 Uiso 1 1 calc R . . O3 O 0.18655(12) 0.61205(14) 0.51576(9) 0.0572(4) Uani 1 1 d . . . H3 H 0.1394 0.5401 0.5189 0.086 Uiso 1 1 calc R . . C8 C 0.2042(5) 0.7618(5) 0.7859(2) 0.1273(14) Uani 1 1 d . . . H8 H 0.2583 0.8198 0.8196 0.153 Uiso 1 1 calc R . . C1 C 0.1308(4) 0.6597(4) 0.82134(18) 0.1083(11) Uani 1 1 d . . . H1 H 0.1331 0.6465 0.8795 0.130 Uiso 1 1 calc R . . C2 C 0.0540(4) 0.5767(4) 0.77298(18) 0.1075(11) Uani 1 1 d . . . H2A H 0.0029 0.5043 0.7973 0.129 Uiso 1 1 calc R . . C3 C 0.0498(3) 0.5969(3) 0.68840(15) 0.0822(8) Uani 1 1 d . . . H3A H -0.0048 0.5386 0.6551 0.099 Uiso 1 1 calc R . . C4 C 0.12363(17) 0.7002(2) 0.65207(12) 0.0515(5) Uani 1 1 d . . . C5 C 0.12213(17) 0.72156(18) 0.55939(12) 0.0464(5) Uani 1 1 d . . . H5 H 0.1724 0.8088 0.5473 0.056 Uiso 1 1 calc R . . C6 C -0.01969(18) 0.73992(18) 0.52824(10) 0.0432(5) Uani 1 1 d . . . C7 C 0.2014(3) 0.7826(3) 0.70123(17) 0.0905(9) Uani 1 1 d . . . H7 H 0.2537 0.8544 0.6773 0.109 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 0.0533(8) 0.0461(8) 0.0952(11) -0.0131(7) -0.0207(7) -0.0014(6) O2 0.0474(8) 0.0450(8) 0.0747(9) -0.0091(6) -0.0110(6) 0.0017(6) O3 0.0400(8) 0.0498(8) 0.0820(10) -0.0137(6) 0.0110(6) -0.0055(6) C8 0.162(4) 0.137(3) 0.0825(19) -0.011(2) -0.057(2) -0.012(3) C1 0.131(3) 0.135(3) 0.0582(16) 0.0005(18) -0.0147(17) 0.032(2) C2 0.122(3) 0.126(3) 0.0748(19) 0.0306(18) 0.0033(17) -0.008(2) C3 0.0920(19) 0.0895(17) 0.0651(14) 0.0105(13) -0.0044(13) -0.0192(14) C4 0.0391(10) 0.0551(11) 0.0603(12) -0.0016(9) -0.0058(8) 0.0076(9) C5 0.0368(10) 0.0412(9) 0.0611(11) -0.0049(8) 0.0026(8) -0.0040(7) C6 0.0426(10) 0.0384(9) 0.0485(9) 0.0007(7) 0.0021(7) -0.0046(8) C7 0.094(2) 0.098(2) 0.0798(16) -0.0023(14) -0.0326(15) -0.0220(16) _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 C6 1.207(2) . ? O2 C6 1.307(2) . ? O2 H2 0.8400 . ? O3 C5 1.424(2) . ? O3 H3 0.8400 . ? C8 C1 1.354(5) . ? C8 C7 1.384(4) . ? C8 H8 0.9500 . ? C1 C2 1.357(5) . ? C1 H1 0.9500 . ? C2 C3 1.382(4) . ? C2 H2A 0.9500 . ? C3 C4 1.372(3) . ? C3 H3A 0.9500 . ? C4 C7 1.366(3) . ? C4 C5 1.513(3) . ? C5 C6 1.509(3) . ? C5 H5 1.0000 . ? C7 H7 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O2 H2 109.5 . . ? C5 O3 H3 109.5 . . ? C1 C8 C7 121.0(3) . . ? C1 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C1 C2 119.4(3) . . ? C8 C1 H1 120.3 . . ? C2 C1 H1 120.3 . . ? C1 C2 C3 120.3(3) . . ? C1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? C4 C3 C2 120.7(3) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C7 C4 C3 118.6(2) . . ? C7 C4 C5 120.2(2) . . ? C3 C4 C5 121.20(18) . . ? O3 C5 C6 110.06(14) . . ? O3 C5 C4 112.64(16) . . ? C6 C5 C4 110.85(14) . . ? O3 C5 H5 107.7 . . ? C6 C5 H5 107.7 . . ? C4 C5 H5 107.7 . . ? O1 C6 O2 123.59(17) . . ? O1 C6 C5 123.48(16) . . ? O2 C6 C5 112.93(15) . . ? C4 C7 C8 120.1(3) . . ? C4 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.119 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.035