# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_General _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 #TrackingRef 'web_deposit_cif_file_0_AkioKamimura_1323265663.SS01089.cif' _audit_creation_date 2008-02-01 _audit_creation_method 'by CrystalStructure 3.8.2' _audit_update_record ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Prof Hidemitsu Uno' _publ_contact_author_email uno@dpc.ehime-u.ac.jp _publ_contact_author_fax +81-89-927-9670 _publ_contact_author_phone +81-89-927-9660 _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_category CO _publ_requested_coeditor_name ? loop_ _publ_author_name 'Akio Kamimura' K.Miyazaki S.Suzuki S.Ishikawa H.Uno #============================================================================== data___SS01089 _database_code_depnum_ccdc_archive 'CCDC 857315' #TrackingRef 'web_deposit_cif_file_0_AkioKamimura_1323265663.SS01089.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C10 H15 N O6 ' _chemical_formula_moiety 'C10 H15 N O6 ' _chemical_formula_weight 245.23 _chemical_melting_point ? _chemical_absolute_configuration syn #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 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' 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' _cell_length_a 7.4247(7) _cell_length_b 9.3395(9) _cell_length_c 16.7423(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1160.96(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5148 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode (50 kV, 200 mA)' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury-7' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.7059 _diffrn_reflns_number 13109 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_min -8 _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 21 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 #============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR97 _computing_structure_refinement SHELXL97 _computing_publication_material 'CrystalStructure 3.8.2' _computing_molecular_graphics ? #============================================================================== _reflns_number_total 1541 _reflns_number_gt 1492 _reflns_threshold_expression >2sigma(I) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The Friedel pairs are merged. ; _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^)+(0.0439P)^2^+0.2426P] 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_number_reflns 1541 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0833 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.170 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.039 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 0.3625(2) -0.09782(15) 0.24203(8) 0.0392(4) Uani 1 1 d . . . O2 O 0.08579(19) 0.07395(12) 0.19674(7) 0.0255(3) Uani 1 1 d . . . O3 O 0.12897(18) 0.31373(12) 0.20778(6) 0.0239(3) Uani 1 1 d . . . O4 O 0.05169(17) 0.32970(14) 0.37790(7) 0.0250(3) Uani 1 1 d . . . H4 H -0.0176 0.3849 0.3529 0.038 Uiso 1 1 calc R . . O5 O 0.4011(2) 0.49083(16) 0.47595(9) 0.0441(4) Uani 1 1 d . . . O6 O 0.2525(2) 0.32399(18) 0.53594(7) 0.0390(4) Uani 1 1 d . . . N1 N 0.3364(2) 0.37020(17) 0.47898(8) 0.0276(3) Uani 1 1 d . . . C1 C 0.3196(2) -0.00513(18) 0.28860(10) 0.0252(4) Uani 1 1 d . . . C2 C 0.1680(2) 0.09699(17) 0.27223(9) 0.0199(3) Uani 1 1 d . . . H2 H 0.0756 0.0899 0.3155 0.024 Uiso 1 1 calc R . . C3 C 0.2410(2) 0.25146(16) 0.26756(9) 0.0198(3) Uani 1 1 d . . . H3 H 0.3690 0.2504 0.2490 0.024 Uiso 1 1 calc R . . C4 C 0.2258(2) 0.33669(17) 0.34422(9) 0.0207(3) Uani 1 1 d . . . H4A H 0.2562 0.4390 0.3330 0.025 Uiso 1 1 calc R . . C5 C 0.3595(2) 0.27727(18) 0.40554(9) 0.0214(3) Uani 1 1 d . . . H5 H 0.4842 0.2917 0.3844 0.026 Uiso 1 1 calc R . . C6 C 0.3382(2) 0.12025(19) 0.42817(10) 0.0243(4) Uani 1 1 d . . . H6A H 0.2084 0.0988 0.4344 0.029 Uiso 1 1 calc R . . H6B H 0.3969 0.1039 0.4805 0.029 Uiso 1 1 calc R . . C7 C 0.4188(3) 0.0163(2) 0.36683(10) 0.0291(4) Uani 1 1 d . . . H7A H 0.5421 0.0496 0.3541 0.035 Uiso 1 1 calc R . . H7B H 0.4305 -0.0785 0.3929 0.035 Uiso 1 1 calc R . . C8 C 0.0980(3) 0.20363(18) 0.15033(9) 0.0252(4) Uani 1 1 d . . . C9 C -0.0815(3) 0.2296(2) 0.11123(12) 0.0374(5) Uani 1 1 d . . . H9A H -0.1759 0.2320 0.1521 0.056 Uiso 1 1 calc R . . H9B H -0.1068 0.1524 0.0732 0.056 Uiso 1 1 calc R . . H9C H -0.0788 0.3214 0.0829 0.056 Uiso 1 1 calc R . . C10 C 0.2518(3) 0.1927(2) 0.09145(11) 0.0390(5) Uani 1 1 d . . . H10A H 0.2589 0.2811 0.0601 0.058 Uiso 1 1 calc R . . H10B H 0.2310 0.1114 0.0556 0.058 Uiso 1 1 calc R . . H10C H 0.3650 0.1784 0.1205 0.058 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 0.0444(8) 0.0363(8) 0.0370(7) -0.0118(6) -0.0011(6) 0.0147(7) O2 0.0355(7) 0.0197(5) 0.0213(6) 0.0013(4) -0.0082(5) -0.0049(6) O3 0.0347(7) 0.0193(5) 0.0177(5) 0.0003(4) -0.0027(5) 0.0001(5) O4 0.0240(6) 0.0291(6) 0.0220(6) 0.0022(5) 0.0020(5) 0.0073(5) O5 0.0554(10) 0.0342(8) 0.0427(8) -0.0149(6) -0.0055(7) -0.0051(8) O6 0.0369(8) 0.0586(9) 0.0215(6) -0.0027(6) 0.0035(6) 0.0110(8) N1 0.0259(8) 0.0342(8) 0.0228(7) -0.0073(6) -0.0060(6) 0.0062(7) C1 0.0252(8) 0.0220(8) 0.0284(9) -0.0009(7) 0.0013(7) 0.0023(7) C2 0.0230(8) 0.0193(8) 0.0175(7) -0.0005(5) -0.0016(6) -0.0017(7) C3 0.0232(8) 0.0192(7) 0.0170(7) 0.0007(5) 0.0014(6) -0.0016(7) C4 0.0239(8) 0.0191(7) 0.0192(7) -0.0004(6) 0.0006(6) -0.0002(7) C5 0.0209(8) 0.0253(8) 0.0179(7) -0.0030(6) 0.0008(6) -0.0003(7) C6 0.0239(8) 0.0264(8) 0.0225(8) 0.0032(6) -0.0039(6) 0.0013(7) C7 0.0267(9) 0.0268(9) 0.0338(9) -0.0031(7) -0.0073(7) 0.0072(8) C8 0.0370(10) 0.0203(8) 0.0183(7) 0.0004(6) -0.0024(7) -0.0037(8) C9 0.0480(12) 0.0307(9) 0.0334(9) 0.0011(8) -0.0165(9) 0.0013(10) C10 0.0550(13) 0.0370(11) 0.0250(9) -0.0078(8) 0.0117(9) -0.0101(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.208(2) . ? O2 C2 1.4200(19) . ? O2 C8 1.4419(19) . ? O3 C3 1.4254(19) . ? O3 C8 1.4267(19) . ? O4 C4 1.412(2) . ? O4 H4 0.8400 . ? O5 N1 1.226(2) . ? O6 N1 1.218(2) . ? N1 C5 1.515(2) . ? C1 C2 1.500(2) . ? C1 C7 1.516(2) . ? C2 C3 1.543(2) . ? C2 H2 1.0000 . ? C3 C4 1.515(2) . ? C3 H3 1.0000 . ? C4 C5 1.532(2) . ? C4 H4A 1.0000 . ? C5 C6 1.523(2) . ? C5 H5 1.0000 . ? C6 C7 1.535(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.505(3) . ? C8 C10 1.512(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 C8 108.99(12) . . ? C3 O3 C8 105.87(12) . . ? C4 O4 H4 109.5 . . ? O6 N1 O5 123.95(16) . . ? O6 N1 C5 119.36(16) . . ? O5 N1 C5 116.66(15) . . ? O1 C1 C2 122.37(16) . . ? O1 C1 C7 121.61(17) . . ? C2 C1 C7 116.01(15) . . ? O2 C2 C1 112.88(14) . . ? O2 C2 C3 104.33(12) . . ? C1 C2 C3 109.88(14) . . ? O2 C2 H2 109.9 . . ? C1 C2 H2 109.9 . . ? C3 C2 H2 109.9 . . ? O3 C3 C4 109.69(13) . . ? O3 C3 C2 102.24(12) . . ? C4 C3 C2 114.97(12) . . ? O3 C3 H3 109.9 . . ? C4 C3 H3 109.9 . . ? C2 C3 H3 109.9 . . ? O4 C4 C3 112.49(14) . . ? O4 C4 C5 108.01(12) . . ? C3 C4 C5 109.21(13) . . ? O4 C4 H4A 109.0 . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? N1 C5 C6 109.76(13) . . ? N1 C5 C4 105.23(13) . . ? C6 C5 C4 116.61(14) . . ? N1 C5 H5 108.3 . . ? C6 C5 H5 108.3 . . ? C4 C5 H5 108.3 . . ? C5 C6 C7 113.72(14) . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C1 C7 C6 118.16(15) . . ? C1 C7 H7A 107.8 . . ? C6 C7 H7A 107.8 . . ? C1 C7 H7B 107.8 . . ? C6 C7 H7B 107.8 . . ? H7A C7 H7B 107.1 . . ? O3 C8 O2 104.60(11) . . ? O3 C8 C9 108.65(15) . . ? O2 C8 C9 108.32(15) . . ? O3 C8 C10 111.51(15) . . ? O2 C8 C10 110.00(16) . . ? C9 C8 C10 113.34(15) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 O2 C2 C1 -121.78(16) . . . . ? C8 O2 C2 C3 -2.51(17) . . . . ? O1 C1 C2 O2 -1.2(3) . . . . ? C7 C1 C2 O2 177.80(15) . . . . ? O1 C1 C2 C3 -117.16(19) . . . . ? C7 C1 C2 C3 61.80(18) . . . . ? C8 O3 C3 C4 -159.09(13) . . . . ? C8 O3 C3 C2 -36.65(15) . . . . ? O2 C2 C3 O3 23.78(15) . . . . ? C1 C2 C3 O3 145.05(13) . . . . ? O2 C2 C3 C4 142.55(15) . . . . ? C1 C2 C3 C4 -96.17(16) . . . . ? O3 C3 C4 O4 65.26(16) . . . . ? C2 C3 C4 O4 -49.26(18) . . . . ? O3 C3 C4 C5 -174.83(13) . . . . ? C2 C3 C4 C5 70.64(17) . . . . ? O6 N1 C5 C6 -23.0(2) . . . . ? O5 N1 C5 C6 158.85(16) . . . . ? O6 N1 C5 C4 103.24(17) . . . . ? O5 N1 C5 C4 -74.92(19) . . . . ? O4 C4 C5 N1 -58.27(17) . . . . ? C3 C4 C5 N1 179.11(13) . . . . ? O4 C4 C5 C6 63.63(18) . . . . ? C3 C4 C5 C6 -58.99(18) . . . . ? N1 C5 C6 C7 -160.83(14) . . . . ? C4 C5 C6 C7 79.68(19) . . . . ? O1 C1 C7 C6 -170.66(18) . . . . ? C2 C1 C7 C6 10.4(2) . . . . ? C5 C6 C7 C1 -73.6(2) . . . . ? C3 O3 C8 O2 35.97(17) . . . . ? C3 O3 C8 C9 151.48(14) . . . . ? C3 O3 C8 C10 -82.89(17) . . . . ? C2 O2 C8 O3 -19.85(18) . . . . ? C2 O2 C8 C9 -135.60(15) . . . . ? C2 O2 C8 C10 100.02(16) . . . . ? #============================================================================== data_201000912 _database_code_depnum_ccdc_archive 'CCDC 868308' #TrackingRef 'KM02051-B.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C15 H25 N O6' _chemical_formula_moiety 'C15 H25 N O6' _chemical_formula_weight 315.37 _chemical_melting_point ? _chemical_absolute_configuration rm #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 10.8043(4) _cell_length_b 5.7743(2) _cell_length_c 14.0245(5) _cell_angle_alpha 90.0000 _cell_angle_beta 110.0621(18) _cell_angle_gamma 90.0000 _cell_volume 821.85(5) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5912 _cell_measurement_theta_min 3.36 _cell_measurement_theta_max 68.10 _cell_measurement_temperature 293 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_min 0.080 _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340.00 _exptl_absorpt_coefficient_mu 0.820 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 9427 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_theta_max 68.10 _diffrn_reflns_theta_full 68.10 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2849 _reflns_number_gt 2555 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0902 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2849 _refine_ls_number_parameters 225 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.0139P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.140 _refine_diff_density_min -0.200 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1196 Friedel Pairs' _refine_ls_abs_structure_Flack 0.11(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.05133(10) 0.7388(3) -0.09149(7) 0.0447(4) Uani 1.0 2 d . . . O2 O 0.22471(11) 0.8031(3) -0.14664(7) 0.0451(3) Uani 1.0 2 d . . . O3 O 0.41422(14) 1.1018(3) -0.05563(11) 0.0698(5) Uani 1.0 2 d . . . O4 O 0.18972(12) 0.4715(3) 0.09028(9) 0.0456(3) Uani 1.0 2 d . . . O5 O 0.29455(14) 1.0605(3) 0.36295(9) 0.0557(4) Uani 1.0 2 d . . . O6 O 0.27665(13) 0.7151(3) 0.43661(8) 0.0503(4) Uani 1.0 2 d . . . N1 N 0.25647(14) 0.7234(4) 0.27466(9) 0.0467(4) Uani 1.0 2 d . . . C1 C 0.00945(18) 0.8176(4) -0.26876(12) 0.0528(5) Uani 1.0 2 d . . . C2 C 0.09860(17) 0.6961(4) -0.17584(11) 0.0402(4) Uani 1.0 2 d . . . C3 C 0.1073(3) 0.4391(4) -0.19006(16) 0.0568(5) Uani 1.0 2 d . . . C4 C 0.15752(14) 0.8290(4) -0.00715(11) 0.0361(4) Uani 1.0 2 d . . . C5 C 0.27883(15) 0.7919(4) -0.03935(11) 0.0377(4) Uani 1.0 2 d . . . C6 C 0.38076(15) 0.9792(4) 0.00086(12) 0.0436(4) Uani 1.0 2 d . . . C7 C 0.43599(18) 1.0123(4) 0.11431(13) 0.0493(5) Uani 1.0 2 d . . . C8 C 0.40537(15) 0.8295(4) 0.18169(12) 0.0462(5) Uani 1.0 2 d . . . C9 C 0.26376(16) 0.8315(4) 0.18240(11) 0.0407(4) Uani 1.0 2 d . . . C10 C 0.16147(15) 0.7114(4) 0.09076(11) 0.0373(4) Uani 1.0 2 d . . . C11 C 0.27840(16) 0.8527(4) 0.35931(11) 0.0421(5) Uani 1.0 2 d . . . C12 C 0.28892(18) 0.8168(4) 0.53614(11) 0.0489(5) Uani 1.0 2 d . . . C13 C 0.1746(3) 0.9787(5) 0.52373(16) 0.0684(7) Uani 1.0 2 d . . . C14 C 0.2791(3) 0.6046(5) 0.59697(16) 0.0734(7) Uani 1.0 2 d . . . C15 C 0.4210(3) 0.9361(6) 0.58216(15) 0.0728(7) Uani 1.0 2 d . . . H4 H 0.1205 0.3895 0.0921 0.0684 Uiso 1.0 2 calc R . . H1 H 0.2415 0.6040 0.2750 0.0561 Uiso 1.0 2 calc R . . H1A H 0.0097 0.9839 -0.2554 0.0792 Uiso 1.0 2 calc R . . H1B H -0.0802 0.7574 -0.2859 0.0792 Uiso 1.0 2 calc R . . H1C H 0.0408 0.7906 -0.3255 0.0792 Uiso 1.0 2 calc R . . H3A H 0.1423 0.4093 -0.2458 0.0853 Uiso 1.0 2 calc R . . H3B H 0.0182 0.3695 -0.2076 0.0853 Uiso 1.0 2 calc R . . H3C H 0.1671 0.3691 -0.1262 0.0853 Uiso 1.0 2 calc R . . H4A H 0.1432 1.0067 -0.0011 0.0433 Uiso 1.0 2 calc R . . H5 H 0.3188 0.6344 -0.0168 0.0452 Uiso 1.0 2 calc R . . H7A H 0.4045 1.1609 0.1298 0.0591 Uiso 1.0 2 calc R . . H7B H 0.5315 1.0237 0.1340 0.0591 Uiso 1.0 2 calc R . . H8A H 0.4647 0.8511 0.2502 0.0555 Uiso 1.0 2 calc R . . H8B H 0.4230 0.6789 0.1596 0.0555 Uiso 1.0 2 calc R . . H9 H 0.2369 0.9943 0.1824 0.0489 Uiso 1.0 2 calc R . . H10 H 0.0708 0.7290 0.0978 0.0448 Uiso 1.0 2 calc R . . H13A H 0.1819 1.1162 0.4824 0.1026 Uiso 1.0 2 calc R . . H13B H 0.1762 1.0317 0.5922 0.1026 Uiso 1.0 2 calc R . . H13C H 0.0898 0.8956 0.4884 0.1026 Uiso 1.0 2 calc R . . H14A H 0.1908 0.5353 0.5672 0.1100 Uiso 1.0 2 calc R . . H14B H 0.2939 0.6500 0.6678 0.1100 Uiso 1.0 2 calc R . . H14C H 0.3464 0.4905 0.5955 0.1100 Uiso 1.0 2 calc R . . H15A H 0.4931 0.8252 0.5849 0.1093 Uiso 1.0 2 calc R . . H15B H 0.4318 0.9891 0.6523 0.1093 Uiso 1.0 2 calc R . . H15C H 0.4252 1.0725 0.5396 0.1093 Uiso 1.0 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0325(6) 0.0671(10) 0.0359(5) -0.0045(6) 0.0136(5) -0.0094(6) O2 0.0400(7) 0.0591(9) 0.0395(6) -0.0105(6) 0.0179(5) -0.0013(6) O3 0.0597(9) 0.0811(13) 0.0641(8) -0.0285(9) 0.0155(7) 0.0159(8) O4 0.0452(7) 0.0419(8) 0.0535(7) -0.0028(6) 0.0219(6) -0.0010(6) O5 0.0724(9) 0.0508(9) 0.0467(7) -0.0072(8) 0.0241(6) -0.0061(6) O6 0.0637(8) 0.0517(9) 0.0360(5) -0.0005(7) 0.0177(5) -0.0044(6) N1 0.0531(9) 0.0520(10) 0.0367(7) -0.0062(8) 0.0173(6) -0.0053(7) C1 0.0531(11) 0.0587(13) 0.0433(9) -0.0077(10) 0.0123(8) -0.0008(9) C2 0.0409(9) 0.0449(11) 0.0393(8) -0.0071(8) 0.0195(7) -0.0056(8) C3 0.0677(13) 0.0464(13) 0.0684(12) -0.0051(10) 0.0388(10) -0.0052(10) C4 0.0286(8) 0.0421(10) 0.0367(7) 0.0009(7) 0.0102(6) -0.0043(7) C5 0.0329(8) 0.0447(11) 0.0384(7) -0.0012(8) 0.0160(6) 0.0001(7) C6 0.0326(9) 0.0474(11) 0.0505(9) -0.0024(8) 0.0137(7) 0.0043(9) C7 0.0395(10) 0.0545(13) 0.0538(10) -0.0107(9) 0.0161(8) -0.0085(9) C8 0.0368(9) 0.0592(12) 0.0400(8) -0.0019(9) 0.0098(7) -0.0043(9) C9 0.0402(9) 0.0470(11) 0.0355(8) -0.0006(8) 0.0136(6) -0.0051(8) C10 0.0302(8) 0.0444(11) 0.0395(8) 0.0006(7) 0.0147(6) -0.0048(8) C11 0.0394(9) 0.0503(13) 0.0361(8) -0.0006(8) 0.0124(7) -0.0040(8) C12 0.0570(11) 0.0558(12) 0.0346(8) 0.0026(10) 0.0168(7) -0.0041(8) C13 0.0754(15) 0.0769(17) 0.0635(12) 0.0165(14) 0.0377(11) 0.0064(12) C14 0.1002(18) 0.0724(19) 0.0509(11) 0.0052(15) 0.0302(11) 0.0073(11) C15 0.0679(14) 0.092(2) 0.0503(11) -0.0099(14) 0.0096(10) -0.0180(12) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O1 C2 1.461(3) yes . . O1 C4 1.4338(17) yes . . O2 C2 1.422(3) yes . . O2 C5 1.4165(17) yes . . O3 C6 1.207(3) yes . . O4 C10 1.419(3) yes . . O5 C11 1.211(3) yes . . O6 C11 1.349(3) yes . . O6 C12 1.478(3) yes . . N1 C9 1.463(3) yes . . N1 C11 1.353(3) yes . . C1 C2 1.502(3) yes . . C2 C3 1.504(3) yes . . C4 C5 1.541(3) yes . . C4 C10 1.519(3) yes . . C5 C6 1.508(3) yes . . C6 C7 1.508(3) yes . . C7 C8 1.527(3) yes . . C8 C9 1.533(3) yes . . C9 C10 1.542(2) yes . . C12 C13 1.511(4) yes . . C12 C14 1.518(4) yes . . C12 C15 1.515(3) yes . . O4 H4 0.893 no . . N1 H1 0.708 no . . C1 H1A 0.978 no . . C1 H1B 0.978 no . . C1 H1C 0.978 no . . C3 H3A 0.993 no . . C3 H3B 0.993 no . . C3 H3C 0.993 no . . C4 H4A 1.045 no . . C5 H5 1.010 no . . C7 H7A 0.975 no . . C7 H7B 0.975 no . . C8 H8A 0.963 no . . C8 H8B 0.963 no . . C9 H9 0.984 no . . C10 H10 1.023 no . . C13 H13A 1.001 no . . C13 H13B 1.002 no . . C13 H13C 1.002 no . . C14 H14A 0.986 no . . C14 H14B 0.986 no . . C14 H14C 0.986 no . . C15 H15A 0.999 no . . C15 H15B 0.999 no . . C15 H15C 0.999 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C2 O1 C4 109.04(12) yes . . . C2 O2 C5 106.95(13) yes . . . C11 O6 C12 120.23(16) yes . . . C9 N1 C11 119.64(18) yes . . . O1 C2 O2 105.06(12) yes . . . O1 C2 C1 108.98(16) yes . . . O1 C2 C3 109.20(17) yes . . . O2 C2 C1 108.23(16) yes . . . O2 C2 C3 111.68(16) yes . . . C1 C2 C3 113.34(15) yes . . . O1 C4 C5 103.18(13) yes . . . O1 C4 C10 110.46(15) yes . . . C5 C4 C10 116.08(14) yes . . . O2 C5 C4 102.84(11) yes . . . O2 C5 C6 110.29(15) yes . . . C4 C5 C6 112.08(16) yes . . . O3 C6 C5 121.34(15) yes . . . O3 C6 C7 121.29(17) yes . . . C5 C6 C7 117.34(17) yes . . . C6 C7 C8 118.31(17) yes . . . C7 C8 C9 115.29(16) yes . . . N1 C9 C8 111.04(13) yes . . . N1 C9 C10 107.74(16) yes . . . C8 C9 C10 114.99(15) yes . . . O4 C10 C4 111.81(15) yes . . . O4 C10 C9 110.42(13) yes . . . C4 C10 C9 110.01(16) yes . . . O5 C11 O6 126.22(16) yes . . . O5 C11 N1 124.27(17) yes . . . O6 C11 N1 109.49(18) yes . . . O6 C12 C13 109.40(13) yes . . . O6 C12 C14 102.07(18) yes . . . O6 C12 C15 110.43(17) yes . . . C13 C12 C14 110.6(2) yes . . . C13 C12 C15 112.4(2) yes . . . C14 C12 C15 111.39(16) yes . . . C10 O4 H4 109.475 no . . . C9 N1 H1 120.192 no . . . C11 N1 H1 120.168 no . . . C2 C1 H1A 109.473 no . . . C2 C1 H1B 109.476 no . . . C2 C1 H1C 109.467 no . . . H1A C1 H1B 109.475 no . . . H1A C1 H1C 109.469 no . . . H1B C1 H1C 109.467 no . . . C2 C3 H3A 109.465 no . . . C2 C3 H3B 109.476 no . . . C2 C3 H3C 109.473 no . . . H3A C3 H3B 109.462 no . . . H3A C3 H3C 109.468 no . . . H3B C3 H3C 109.482 no . . . O1 C4 H4A 108.948 no . . . C5 C4 H4A 108.950 no . . . C10 C4 H4A 108.946 no . . . O2 C5 H5 110.471 no . . . C4 C5 H5 110.469 no . . . C6 C5 H5 110.468 no . . . C6 C7 H7A 107.736 no . . . C6 C7 H7B 107.731 no . . . C8 C7 H7A 107.727 no . . . C8 C7 H7B 107.734 no . . . H7A C7 H7B 107.113 no . . . C7 C8 H8A 108.446 no . . . C7 C8 H8B 108.450 no . . . C9 C8 H8A 108.455 no . . . C9 C8 H8B 108.455 no . . . H8A C8 H8B 107.483 no . . . N1 C9 H9 107.594 no . . . C8 C9 H9 107.596 no . . . C10 C9 H9 107.592 no . . . O4 C10 H10 108.165 no . . . C4 C10 H10 108.163 no . . . C9 C10 H10 108.164 no . . . C12 C13 H13A 109.480 no . . . C12 C13 H13B 109.470 no . . . C12 C13 H13C 109.468 no . . . H13A C13 H13B 109.474 no . . . H13A C13 H13C 109.471 no . . . H13B C13 H13C 109.464 no . . . C12 C14 H14A 109.469 no . . . C12 C14 H14B 109.474 no . . . C12 C14 H14C 109.476 no . . . H14A C14 H14B 109.470 no . . . H14A C14 H14C 109.466 no . . . H14B C14 H14C 109.472 no . . . C12 C15 H15A 109.471 no . . . C12 C15 H15B 109.474 no . . . C12 C15 H15C 109.472 no . . . H15A C15 H15B 109.473 no . . . H15A C15 H15C 109.464 no . . . H15B C15 H15C 109.473 no . . . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C2 O1 C4 C5 -10.90(17) no . . . . C2 O1 C4 C10 -135.61(14) no . . . . C4 O1 C2 O2 -10.84(18) no . . . . C4 O1 C2 C1 -126.63(14) no . . . . C4 O1 C2 C3 109.08(14) no . . . . C2 O2 C5 C4 -36.76(17) no . . . . C2 O2 C5 C6 -156.45(13) no . . . . C5 O2 C2 O1 30.43(17) no . . . . C5 O2 C2 C1 146.74(13) no . . . . C5 O2 C2 C3 -87.83(15) no . . . . C11 O6 C12 C13 61.6(2) no . . . . C11 O6 C12 C14 178.81(13) no . . . . C11 O6 C12 C15 -62.7(2) no . . . . C12 O6 C11 O5 3.1(3) no . . . . C12 O6 C11 N1 -175.72(13) no . . . . C9 N1 C11 O5 5.9(3) no . . . . C9 N1 C11 O6 -175.34(13) no . . . . C11 N1 C9 C8 87.00(19) no . . . . C11 N1 C9 C10 -146.25(14) no . . . . O1 C4 C5 O2 28.74(17) no . . . . O1 C4 C5 C6 147.19(12) no . . . . O1 C4 C10 O4 64.39(17) no . . . . O1 C4 C10 C9 -172.54(13) no . . . . C5 C4 C10 O4 -52.58(18) no . . . . C5 C4 C10 C9 70.48(19) no . . . . C10 C4 C5 O2 149.70(14) no . . . . C10 C4 C5 C6 -91.86(18) no . . . . O2 C5 C6 O3 -5.7(3) no . . . . O2 C5 C6 C7 172.36(13) no . . . . C4 C5 C6 O3 -119.67(17) no . . . . C4 C5 C6 C7 58.42(18) no . . . . O3 C6 C7 C8 -170.95(17) no . . . . C5 C6 C7 C8 11.0(3) no . . . . C6 C7 C8 C9 -73.3(3) no . . . . C7 C8 C9 N1 -157.18(15) no . . . . C7 C8 C9 C10 80.2(2) no . . . . N1 C9 C10 O4 -60.34(19) no . . . . N1 C9 C10 C4 175.78(13) no . . . . C8 C9 C10 O4 64.1(2) no . . . . C8 C9 C10 C4 -59.8(2) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O1 O4 2.9159(16) no . . O2 O3 2.6467(19) no . . O3 C4 3.454(3) no . . O4 N1 2.8361(19) no . . O4 C5 2.976(3) no . . O4 C8 3.049(3) no . . O5 C8 3.430(3) no . . O5 C9 2.774(3) no . . O5 C12 2.826(3) no . . O5 C13 2.999(4) no . . O5 C15 2.992(3) no . . O6 C9 3.583(2) no . . C1 C4 3.464(2) no . . C1 C5 3.524(2) no . . C2 C6 3.595(3) no . . C2 C10 3.565(3) no . . C3 C4 3.315(3) no . . C3 C5 3.060(3) no . . C4 C7 3.092(3) no . . C4 C8 3.0527(19) no . . C5 C8 2.936(2) no . . C5 C9 3.178(3) no . . C6 C9 3.319(3) no . . C6 C10 3.412(3) no . . C7 C10 3.354(3) no . . C8 C11 3.233(3) no . . C11 C13 2.980(4) no . . C11 C15 3.012(3) no . . O1 O4 2.9357(19) no . 2_555 O1 C10 3.571(3) no . 2_555 O3 O3 3.496(3) no . 2_645 O3 O3 3.496(3) no . 2_655 O3 C5 3.308(2) no . 2_655 O3 C6 3.013(3) no . 2_655 O3 C7 3.135(3) no . 2_655 O3 C8 3.319(3) no . 2_655 O4 O1 2.9357(19) no . 2_545 O5 C1 3.429(3) no . 2_555 C1 O5 3.429(3) no . 2_545 C5 O3 3.308(2) no . 2_645 C6 O3 3.013(3) no . 2_645 C7 O3 3.135(3) no . 2_645 C8 O3 3.319(3) no . 2_645 C10 O1 3.571(3) no . 2_545 O1 H4 3.1519 no . . O1 H1A 2.6037 no . . O1 H1B 2.6089 no . . O1 H1C 3.2582 no . . O1 H3A 3.2749 no . . O1 H3B 2.6321 no . . O1 H3C 2.6033 no . . O1 H5 2.7816 no . . O1 H10 2.5902 no . . O2 H1A 2.5262 no . . O2 H1B 3.2127 no . . O2 H1C 2.6126 no . . O2 H3A 2.6543 no . . O2 H3B 3.2660 no . . O2 H3C 2.6214 no . . O2 H4A 2.7487 no . . O3 H4A 3.3159 no . . O3 H5 3.0048 no . . O3 H7A 2.6604 no . . O3 H7B 2.5630 no . . O4 H1 2.5723 no . . O4 H3C 3.0200 no . . O4 H4A 3.3172 no . . O4 H5 2.5544 no . . O4 H8B 2.6555 no . . O4 H9 3.2542 no . . O5 H1 2.8831 no . . O5 H8A 3.0553 no . . O5 H9 2.4217 no . . O5 H13A 2.4067 no . . O5 H13C 3.4008 no . . O5 H15A 3.3991 no . . O5 H15C 2.3950 no . . O6 H1 2.2586 no . . O6 H13A 2.6972 no . . O6 H13B 3.3018 no . . O6 H13C 2.5874 no . . O6 H14A 2.5411 no . . O6 H14B 3.2057 no . . O6 H14C 2.4621 no . . O6 H15A 2.6193 no . . O6 H15B 3.3147 no . . O6 H15C 2.7076 no . . N1 H4 3.1387 no . . N1 H8A 2.5005 no . . N1 H8B 2.8102 no . . N1 H10 2.6012 no . . C1 H3A 2.7208 no . . C1 H3B 2.7175 no . . C1 H3C 3.3566 no . . C2 H4A 2.9398 no . . C2 H5 2.6686 no . . C3 H1A 3.3438 no . . C3 H1B 2.7236 no . . C3 H1C 2.7028 no . . C3 H5 2.9305 no . . C4 H4 2.9867 no . . C4 H1A 3.4141 no . . C4 H3C 3.1579 no . . C4 H7A 3.3114 no . . C4 H8B 3.1380 no . . C4 H9 2.6735 no . . C5 H1A 3.5805 no . . C5 H3A 3.5364 no . . C5 H3C 2.8096 no . . C5 H7A 3.1309 no . . C5 H7B 3.2559 no . . C5 H8B 2.7671 no . . C5 H9 3.4941 no . . C5 H10 3.4420 no . . C6 H4A 2.5620 no . . C6 H8A 3.3801 no . . C6 H8B 2.7343 no . . C6 H9 3.4088 no . . C7 H4A 3.0190 no . . C7 H5 2.8548 no . . C7 H9 2.6380 no . . C8 H1 2.8514 no . . C8 H4A 3.2650 no . . C8 H5 2.8476 no . . C8 H10 3.4454 no . . C9 H4 3.0280 no . . C9 H4A 2.6540 no . . C9 H5 3.2554 no . . C9 H7A 2.6916 no . . C9 H7B 3.3778 no . . C10 H1 2.5054 no . . C10 H5 2.6694 no . . C10 H7A 3.5978 no . . C10 H8A 3.3705 no . . C10 H8B 2.6608 no . . C11 H8A 2.9163 no . . C11 H9 2.5025 no . . C11 H13A 2.7601 no . . C11 H13C 3.1657 no . . C11 H15A 3.2216 no . . C11 H15C 2.7873 no . . C13 H14A 2.6240 no . . C13 H14B 2.7500 no . . C13 H14C 3.3353 no . . C13 H15A 3.3678 no . . C13 H15B 2.7461 no . . C13 H15C 2.6951 no . . C14 H13A 3.3547 no . . C14 H13B 2.6967 no . . C14 H13C 2.6815 no . . C14 H15A 2.6957 no . . C14 H15B 2.7156 no . . C14 H15C 3.3633 no . . C15 H13A 2.6898 no . . C15 H13B 2.7519 no . . C15 H13C 3.3705 no . . C15 H14A 3.3512 no . . C15 H14B 2.6817 no . . C15 H14C 2.7217 no . . H4 H1 2.7432 no . . H4 H3C 3.2711 no . . H4 H5 3.3425 no . . H4 H8B 3.5000 no . . H4 H10 2.0408 no . . H1 H8A 2.9233 no . . H1 H8B 2.9709 no . . H1 H9 2.5929 no . . H1 H10 2.6377 no . . H1A H3A 3.5975 no . . H1A H4A 3.3595 no . . H1B H3A 3.0339 no . . H1B H3B 2.5601 no . . H1C H3A 2.5411 no . . H1C H3B 2.9971 no . . H3A H5 3.3815 no . . H3C H5 2.3799 no . . H4A H5 2.9252 no . . H4A H7A 2.9287 no . . H4A H9 2.4220 no . . H4A H10 2.4189 no . . H5 H7B 3.3871 no . . H5 H8B 2.3551 no . . H7A H8A 2.3922 no . . H7A H8B 2.8115 no . . H7A H9 2.3802 no . . H7B H8A 2.2314 no . . H7B H8B 2.3993 no . . H7B H9 3.4792 no . . H8A H9 2.4578 no . . H8B H9 2.8110 no . . H9 H10 2.3484 no . . H13A H14A 3.5487 no . . H13A H15A 3.5891 no . . H13A H15B 3.0158 no . . H13A H15C 2.4848 no . . H13B H14A 2.8987 no . . H13B H14B 2.5836 no . . H13B H15B 2.6071 no . . H13B H15C 3.0326 no . . H13C H14A 2.4316 no . . H13C H14B 3.0658 no . . H13C H14C 3.5434 no . . H13C H15C 3.5926 no . . H14A H15B 3.5974 no . . H14B H15A 2.9547 no . . H14B H15B 2.5147 no . . H14B H15C 3.5989 no . . H14C H15A 2.5363 no . . H14C H15B 3.0449 no . . O1 H4 2.0473 no . 2_555 O1 H4A 3.1266 no . 2_545 O1 H9 3.2546 no . 2_545 O1 H10 3.2150 no . 2_545 O1 H10 3.1111 no . 2_555 O2 H3C 3.3576 no . 1_565 O2 H7B 3.0415 no . 2_645 O2 H14B 3.0733 no . 1_554 O3 H3C 2.9459 no . 1_565 O3 H5 3.3464 no . 1_565 O3 H5 2.7157 no . 2_655 O3 H7A 3.5775 no . 2_645 O3 H7B 2.8154 no . 2_655 O3 H8B 2.6793 no . 2_655 O4 H1B 3.5613 no . 2_545 O4 H4A 2.9423 no . 1_545 O4 H4A 3.3851 no . 2_545 O4 H7A 2.8328 no . 1_545 O4 H9 3.0116 no . 1_545 O4 H10 3.4271 no . 2_545 O5 H1 3.3487 no . 1_565 O5 H1B 2.4713 no . 2_555 O5 H3B 3.5120 no . 2_555 O5 H15A 2.6424 no . 2_656 O6 H1A 3.5242 no . 2_545 O6 H1B 3.5890 no . 2_545 O6 H15A 3.4440 no . 2_646 O6 H15C 3.2291 no . 2_646 N1 H1A 3.1184 no . 2_545 N1 H1B 3.3316 no . 2_545 N1 H3B 2.9138 no . 2_555 N1 H15A 3.5821 no . 2_646 N1 H15B 3.4436 no . 2_646 C1 H4 3.2662 no . 2_555 C1 H1 3.1518 no . 2_555 C1 H3B 3.2931 no . 1_565 C1 H13A 3.2177 no . 2_545 C1 H13B 3.3153 no . 1_554 C2 H4 3.1837 no . 2_555 C2 H14B 3.5361 no . 1_554 C3 H1A 2.8635 no . 1_545 C3 H4A 3.5641 no . 1_545 C3 H10 2.9255 no . 2_545 C3 H14B 3.5037 no . 1_554 C4 H4 3.5991 no . 1_565 C4 H4 2.8471 no . 2_555 C4 H3C 3.5555 no . 1_565 C4 H10 3.2987 no . 2_555 C5 H7B 3.1975 no . 2_645 C6 H3C 3.2790 no . 1_565 C6 H5 3.2997 no . 2_655 C6 H7B 3.5530 no . 2_645 C7 H5 3.4448 no . 2_655 C7 H14B 3.5168 no . 2_656 C8 H14C 3.4749 no . 2_656 C8 H15B 3.0929 no . 2_646 C9 H3B 3.1929 no . 2_555 C10 H4 3.3988 no . 2_555 C10 H3B 3.0773 no . 2_555 C10 H4A 3.3130 no . 2_545 C11 H1B 3.0975 no . 2_555 C11 H3B 3.1829 no . 2_555 C11 H15A 3.5812 no . 2_656 C11 H15C 3.4302 no . 2_646 C13 H1B 3.5243 no . 2_555 C13 H1C 3.1366 no . 1_556 C13 H1C 3.4565 no . 2_555 C13 H14A 3.2643 no . 1_565 C13 H14C 3.4510 no . 1_565 C14 H1C 3.2998 no . 1_556 C14 H3A 3.2495 no . 1_556 C14 H8A 3.2130 no . 2_646 C14 H13A 3.2374 no . 1_545 C14 H13B 3.4829 no . 1_545 C15 H8A 3.2867 no . 2_656 C15 H14C 3.3223 no . 1_565 C15 H15A 3.5899 no . 2_656 C15 H15C 3.4683 no . 2_646 H4 O1 2.0473 no . 2_545 H4 C1 3.2662 no . 2_545 H4 C2 3.1837 no . 2_545 H4 C4 3.5991 no . 1_545 H4 C4 2.8471 no . 2_545 H4 C10 3.3988 no . 2_545 H4 H1A 3.1194 no . 2_545 H4 H1B 2.9953 no . 2_545 H4 H4A 2.6224 no . 1_545 H4 H4A 2.7762 no . 2_545 H4 H7A 3.2135 no . 1_545 H4 H9 2.7024 no . 1_545 H4 H10 2.9057 no . 2_545 H1 O5 3.3487 no . 1_545 H1 C1 3.1518 no . 2_545 H1 H1A 2.7228 no . 2_545 H1 H1B 2.6928 no . 2_545 H1 H3B 3.0497 no . 2_555 H1 H15A 3.2874 no . 2_646 H1 H15B 3.3866 no . 2_646 H1A O6 3.5242 no . 2_555 H1A N1 3.1184 no . 2_555 H1A C3 2.8635 no . 1_565 H1A H4 3.1194 no . 2_555 H1A H1 2.7228 no . 2_555 H1A H3A 2.8236 no . 1_565 H1A H3B 2.3181 no . 1_565 H1A H3C 3.0011 no . 1_565 H1A H10 2.9944 no . 2_555 H1A H13B 3.2438 no . 1_554 H1B O4 3.5613 no . 2_555 H1B O5 2.4713 no . 2_545 H1B O6 3.5890 no . 2_555 H1B N1 3.3316 no . 2_555 H1B C11 3.0975 no . 2_545 H1B C13 3.5243 no . 2_545 H1B H4 2.9953 no . 2_555 H1B H1 2.6928 no . 2_555 H1B H9 2.9948 no . 2_545 H1B H13A 2.7185 no . 2_545 H1B H13C 3.4982 no . 2_545 H1C C13 3.1366 no . 1_554 H1C C13 3.4565 no . 2_545 H1C C14 3.2998 no . 1_554 H1C H13A 2.8305 no . 2_545 H1C H13B 2.5638 no . 1_554 H1C H13C 2.8999 no . 1_554 H1C H13C 3.1937 no . 2_545 H1C H14A 2.9562 no . 1_554 H1C H14B 2.8847 no . 1_554 H3A C14 3.2495 no . 1_554 H3A H1A 2.8236 no . 1_545 H3A H7B 3.3949 no . 2_645 H3A H13B 3.2600 no . 1_544 H3A H13C 3.4668 no . 2_545 H3A H14A 2.9377 no . 1_554 H3A H14B 2.7284 no . 1_554 H3B O5 3.5120 no . 2_545 H3B N1 2.9138 no . 2_545 H3B C1 3.2931 no . 1_545 H3B C9 3.1929 no . 2_545 H3B C10 3.0773 no . 2_545 H3B C11 3.1829 no . 2_545 H3B H1 3.0497 no . 2_545 H3B H1A 2.3181 no . 1_545 H3B H4A 3.4516 no . 1_545 H3B H9 2.9852 no . 2_545 H3B H10 2.2299 no . 2_545 H3C O2 3.3576 no . 1_545 H3C O3 2.9459 no . 1_545 H3C C4 3.5555 no . 1_545 H3C C6 3.2790 no . 1_545 H3C H1A 3.0011 no . 1_545 H3C H4A 2.7991 no . 1_545 H3C H7B 3.4143 no . 2_645 H3C H10 2.8499 no . 2_545 H4A O1 3.1266 no . 2_555 H4A O4 2.9423 no . 1_565 H4A O4 3.3851 no . 2_555 H4A C3 3.5641 no . 1_565 H4A C10 3.3130 no . 2_555 H4A H4 2.6224 no . 1_565 H4A H4 2.7762 no . 2_555 H4A H3B 3.4516 no . 1_565 H4A H3C 2.7991 no . 1_565 H4A H10 2.5848 no . 2_555 H5 O3 3.3464 no . 1_545 H5 O3 2.7157 no . 2_645 H5 C6 3.2997 no . 2_645 H5 C7 3.4448 no . 2_645 H5 H7A 3.3546 no . 1_545 H5 H7B 2.7468 no . 2_645 H7A O3 3.5775 no . 2_655 H7A O4 2.8328 no . 1_565 H7A H4 3.2135 no . 1_565 H7A H5 3.3546 no . 1_565 H7A H8B 3.0172 no . 1_565 H7A H14B 3.5120 no . 2_656 H7A H15B 3.5137 no . 2_656 H7B O2 3.0415 no . 2_655 H7B O3 2.8154 no . 2_645 H7B C5 3.1975 no . 2_655 H7B C6 3.5530 no . 2_655 H7B H3A 3.3949 no . 2_655 H7B H3C 3.4143 no . 2_655 H7B H5 2.7468 no . 2_655 H7B H14B 2.8669 no . 2_656 H7B H14C 3.5693 no . 2_656 H8A C14 3.2130 no . 2_656 H8A C15 3.2867 no . 2_646 H8A H14B 3.0073 no . 2_656 H8A H14C 2.5427 no . 2_656 H8A H15A 3.5109 no . 2_656 H8A H15B 2.5375 no . 2_646 H8A H15C 3.2070 no . 2_646 H8B O3 2.6793 no . 2_645 H8B H7A 3.0172 no . 1_545 H8B H15B 2.7889 no . 2_646 H9 O1 3.2546 no . 2_555 H9 O4 3.0116 no . 1_565 H9 H4 2.7024 no . 1_565 H9 H1B 2.9948 no . 2_555 H9 H3B 2.9852 no . 2_555 H10 O1 3.1111 no . 2_545 H10 O1 3.2150 no . 2_555 H10 O4 3.4271 no . 2_555 H10 C3 2.9255 no . 2_555 H10 C4 3.2987 no . 2_545 H10 H4 2.9057 no . 2_555 H10 H1A 2.9944 no . 2_545 H10 H3B 2.2299 no . 2_555 H10 H3C 2.8499 no . 2_555 H10 H4A 2.5848 no . 2_545 H13A C1 3.2177 no . 2_555 H13A C14 3.2374 no . 1_565 H13A H1B 2.7185 no . 2_555 H13A H1C 2.8305 no . 2_555 H13A H13C 3.4944 no . 2_556 H13A H14A 2.6833 no . 1_565 H13A H14C 2.9005 no . 1_565 H13B C1 3.3153 no . 1_556 H13B C14 3.4829 no . 1_565 H13B H1A 3.2438 no . 1_556 H13B H1C 2.5638 no . 1_556 H13B H3A 3.2600 no . 1_566 H13B H13C 3.4245 no . 2_556 H13B H14A 2.9395 no . 1_565 H13B H14C 3.2158 no . 1_565 H13C H1B 3.4982 no . 2_555 H13C H1C 2.8999 no . 1_556 H13C H1C 3.1937 no . 2_555 H13C H3A 3.4668 no . 2_555 H13C H13A 3.4944 no . 2_546 H13C H13B 3.4245 no . 2_546 H13C H13C 3.5554 no . 2_546 H13C H13C 3.5554 no . 2_556 H13C H14A 2.9708 no . 2_556 H14A C13 3.2643 no . 1_545 H14A H1C 2.9562 no . 1_556 H14A H3A 2.9377 no . 1_556 H14A H13A 2.6833 no . 1_545 H14A H13B 2.9395 no . 1_545 H14A H13C 2.9708 no . 2_546 H14B O2 3.0733 no . 1_556 H14B C2 3.5361 no . 1_556 H14B C3 3.5037 no . 1_556 H14B C7 3.5168 no . 2_646 H14B H1C 2.8847 no . 1_556 H14B H3A 2.7284 no . 1_556 H14B H7A 3.5120 no . 2_646 H14B H7B 2.8669 no . 2_646 H14B H8A 3.0073 no . 2_646 H14C C8 3.4749 no . 2_646 H14C C13 3.4510 no . 1_545 H14C C15 3.3223 no . 1_545 H14C H7B 3.5693 no . 2_646 H14C H8A 2.5427 no . 2_646 H14C H13A 2.9005 no . 1_545 H14C H13B 3.2158 no . 1_545 H14C H15B 3.0603 no . 1_545 H14C H15C 2.7609 no . 1_545 H15A O5 2.6424 no . 2_646 H15A O6 3.4440 no . 2_656 H15A N1 3.5821 no . 2_656 H15A C11 3.5812 no . 2_646 H15A C15 3.5899 no . 2_646 H15A H1 3.2874 no . 2_656 H15A H8A 3.5109 no . 2_646 H15A H15C 2.6477 no . 2_646 H15B N1 3.4436 no . 2_656 H15B C8 3.0929 no . 2_656 H15B H1 3.3866 no . 2_656 H15B H7A 3.5137 no . 2_646 H15B H8A 2.5375 no . 2_656 H15B H8B 2.7889 no . 2_656 H15B H14C 3.0603 no . 1_565 H15C O6 3.2291 no . 2_656 H15C C11 3.4302 no . 2_656 H15C C15 3.4683 no . 2_656 H15C H8A 3.2070 no . 2_656 H15C H14C 2.7609 no . 1_565 H15C H15A 2.6477 no . 2_656 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O4 H4 O1 . . 2_545 2.9357(19) 0.893 2.047 172.9 no N1 H1 O4 . . . 2.8361(19) 0.708 2.572 104.7 no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================