# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_coden_Cambridge 440 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address 'A Williams' ; Department of Inorganic, Analytical and Applied Chemistry University of Geneva 30, quai E. Ansermet CH - 1211 Geneva 4 Switzerland ; 'Gerald Bernardinelli' ; Department of Inorganic, Analytical and Applied Chemistry University of Geneva 30, quai E. Ansermet CH - 1211 Geneva 4 Switzerland ; 'Franck Delval' ; Department of Inorganic, Analytical and Applied Chemistry University of Geneva 30, quai E. Ansermet CH - 1211 Geneva 4 Switzerland ; 'Alexandra Spyratou' ; Laboratoiry of X-ray Crystallography University of Geneva 24, quai E. Ansermet CH - 1211 Geneva 4 Switzerland ; 'Simon Verdan' ; Department of Inorganic, Analytical and Applied Chemistry University of Geneva 30, quai E. Ansermet CH - 1211 Geneva 4 Switzerland ; _publ_contact_author_name 'A Williams' _publ_contact_author_email ALAN.WILLIAMS@CHIAM.UNIGE.CH _publ_section_title ; The Clash of the Synthons: Crystal Structures of Benzimidazole-alcohol-carboxylic acids ; _publ_contact_author ; Alan F. Williams Department of Inorganic, Analytical and Applied Chemistry University of Geneva 30, quai E. Ansermet CH - 1211 Geneva 4 Switzerland ; _publ_contact_author_fax '41 (22) 379 61 08' _publ_contact_author_phone '41 (22) 379 62 02' #-------------------------------------------------------------------- _publ_requested_journal 'New Journal of Chemistry' # Attachment 'verdan-1.cif' data_verdan1 _database_code_depnum_ccdc_archive 'CCDC 683798' #--- [RR-1H2]Cl2.2H2O ---------------------------------------------- _audit_creation_date 2007-03-15 _audit_creation_method from_xtal_archive_file_using_CIFIO _audit_update_record 2007-09-19 _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.0.1 _chemical_formula_moiety 'C16 H16 N4 O2, 2(H2 O), 2(Cl)' _chemical_formula_sum 'C16 H20 Cl2 N4 O4' _chemical_formula_weight 403.3 _chemical_absolute_configuration rmad _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,+y,-z 1/2+x,1/2+y,+z 1/2-x,1/2+y,-z _cell_length_a 13.1840(16) _cell_length_b 7.5135(7) _cell_length_c 9.5583(12) _cell_angle_alpha 90.00000 _cell_angle_beta 104.607(15) _cell_angle_gamma 90.00000 _cell_volume 916.2(2) _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_meas not_measured _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _cell_measurement_reflns_used 5447 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 30.3 _cell_measurement_temperature 180 _exptl_absorpt_coefficient_mu 0.385 _exptl_crystal_F_000 420 _exptl_crystal_description prism _exptl_crystal_size_max .24 _exptl_crystal_size_mid .16 _exptl_crystal_size_min .055 _exptl_crystal_colour colourless _diffrn_measurement_device_type 'Stoe Ipds' _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 6 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'XRED; Stoe & Cie, 1999' _exptl_absorpt_correction_T_min .9308 _exptl_absorpt_correction_T_max .9788 _diffrn_reflns_number 8657 _reflns_number_total 2759 _reflns_number_gt 1753 _reflns_threshold_expression 'refl observed if Fo > 3.99 \s(Fo)' _reflns_Friedel_coverage .933 _diffrn_reflns_theta_max 30.36 _diffrn_reflns_theta_full 30.36 _diffrn_measured_fraction_theta_max 1.0 _diffrn_measured_fraction_theta_full 1.0 _diffrn_reflns_av_R_equivalents .065 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_standards_decay_% 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .039 _refine_ls_wR_factor_ref .038 _refine_ls_goodness_of_fit_ref 1.35(3) _refine_ls_number_reflns 1753 _refine_ls_number_parameters 133 _refine_ls_weighting_scheme calc _refine_ls_weighting_details \w=1/[\s^2^(Fo)+0.0005(Fo^2^)] _refine_ls_hydrogen_treatment mixed _refine_ls_shift/su_max .004 _refine_diff_density_max .531 _refine_diff_density_min -1.004 _refine_ls_extinction_method none _refine_ls_abs_structure_details Flack_xabs_refined _refine_ls_abs_structure_Flack -.02(10) _refine_special_details ; Hydrogen treatment: Hydrogen atoms of the water molecule -OH and -NH groups were refined with restraints on bond lengths and bond angles. Other coordinates of H atoms were calculated Definition of polar origin: y(O1) = fixed as a hard constraint ; _computing_data_collection 'EXPOSE (Stoe & Cie, 1999)' _computing_cell_refinement 'CELL (Stoe & Cie, 1999)' _computing_data_reduction 'XRED (Stoe & Cie, 1999)' _computing_structure_solution SIR97 _computing_structure_refinement xtal_CRYLSQ _computing_molecular_graphics xtal_gx3 _computing_publication_material xtal_CIFIO loop_ _atom_type_symbol _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .002 .002 H Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 0 0 N Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .004 .003 O Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .008 .006 Cl Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .132 .159 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 .4006(3) .12300 .5168(3) .0275(14) 1.00000 Uani N1 .4037(3) .4064(5) .2119(4) .0213(16) 1.00000 Uani N2 .4049(3) .1177(5) .2299(4) .0209(16) 1.00000 Uani C1 .3812(4) .3396(7) .0705(4) .0217(19) 1.00000 Uani C2 .3594(4) .4246(7) -.0645(5) .027(3) 1.00000 Uani C3 .3378(4) .3122(7) -.1849(4) .027(3) 1.00000 Uani C4 .3395(4) .1271(8) -.1712(5) .030(3) 1.00000 Uani C5 .3608(4) .0441(6) -.0383(4) .025(3) 1.00000 Uani C6 .3819(4) .1555(6) .0825(4) .0199(18) 1.00000 Uani C7 .4173(4) .2681(7) .3028(4) .0205(17) 1.00000 Uani C8 .4403(3) .2769(6) .4667(4) .0213(17) 1.00000 Uani Cl .66542(8) .7036(3) .41498(11) .0313(5) 1.00000 Uani O1w .4262(3) -.2421(5) .3147(3) .0264(14) 1.00000 Uani H01 .403(5) .515(4) .238(6) .05000 1.00000 Uiso H02 .406(4) .011(4) .262(5) .05000 1.00000 Uiso H101 .3362(16) .124(5) .494(6) .05000 1.00000 Uiso H11w .4931(16) -.245(8) .344(4) .05000 1.00000 Uiso H12w .401(3) -.241(8) .388(3) .05000 1.00000 Uiso H2 .36001 .55456 -.07413 .05000 1.00000 Uiso H3 .32027 .36411 -.28260 .05000 1.00000 Uiso H4 .32479 .05376 -.25858 .05000 1.00000 Uiso H5 .36181 -.08613 -.02954 .05000 1.00000 Uiso H8 .40862 .38474 .49496 .05000 1.00000 Uiso 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 .0258(16) .0380(18) .0197(14) -.0067(14) .0077(12) .0051(12) N1 .0260(19) .0196(18) .0192(16) .0022(17) .0071(14) .0007(14) N2 .0290(19) .0183(18) .0172(15) .0011(15) .0092(13) .0008(13) C1 .020(3) .027(3) .0190(19) .0013(17) .0063(16) .0039(15) C2 .028(3) .029(3) .025(3) .0008(19) .0101(19) .0091(17) C3 .026(3) .040(3) .0160(18) -.001(2) .0061(16) .0039(17) C4 .032(3) .044(3) .0168(19) -.005(3) .0101(17) -.0056(17) C5 .024(3) .031(3) .0205(19) -.0040(18) .0076(17) -.0042(16) C6 .0190(19) .026(3) .0159(17) -.0002(16) .0061(14) .0008(14) C7 .0210(19) .024(3) .0183(16) .0030(18) .0087(14) .0013(16) C8 .028(2) .021(2) .0176(16) .0046(18) .0105(15) .0024(16) Cl .0286(5) .0286(6) .0384(5) .0014(6) .0118(4) -.0031(5) O1w .0275(16) .0264(17) .0257(14) .0011(15) .0071(12) .0024(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance O1 C8 . . 1.402(5) O1 H101 . . .82(2) N1 C1 . . 1.401(5) N1 C7 . . 1.337(6) N1 H01 . . .85(3) N2 C6 . . 1.393(5) N2 C7 . . 1.317(6) N2 H02 . . .86(3) C1 C2 . . 1.403(6) C1 C6 . . 1.387(7) C2 C3 . . 1.398(6) C3 C4 . . 1.396(8) C4 C5 . . 1.380(6) C5 C6 . . 1.396(6) C7 C8 . . 1.520(5) C8 C8 . 2_656 1.543(6) O1w H11w . . .86(2) O1w H12w . . .85(4) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle C8 O1 H101 . . . 110(3) C1 N1 C7 . . . 108.0(4) C1 N1 H01 . . . 127(4) C7 N1 H01 . . . 124(4) C6 N2 C7 . . . 109.0(4) C6 N2 H02 . . . 122(3) C7 N2 H02 . . . 129(4) N1 C1 C2 . . . 131.9(5) N1 C1 C6 . . . 106.4(4) C2 C1 C6 . . . 121.7(4) C1 C2 C3 . . . 115.7(5) C2 C3 C4 . . . 122.0(4) C3 C4 C5 . . . 122.0(4) C4 C5 C6 . . . 116.3(5) N2 C6 C1 . . . 106.4(4) N2 C6 C5 . . . 131.4(4) C1 C6 C5 . . . 122.2(4) N1 C7 N2 . . . 110.1(4) N1 C7 C8 . . . 126.6(4) N2 C7 C8 . . . 123.3(4) O1 C8 C7 . . . 108.8(4) O1 C8 C8 . . 2_656 106.8(3) C7 C8 C8 . . 2_656 110.0(4) H11w O1w H12w . . . 108(4) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion H101 O1 C8 C7 . . . . -69(4) H101 O1 C8 C8 . . . 2_656 172(4) C7 N1 C1 C2 . . . . 179.2(5) C7 N1 C1 C6 . . . . .2(5) H01 N1 C1 C2 . . . . 5(5) H01 N1 C1 C6 . . . . -174(5) C1 N1 C7 N2 . . . . -.2(5) C1 N1 C7 C8 . . . . -178.3(4) H01 N1 C7 N2 . . . . 174(5) H01 N1 C7 C8 . . . . -4(5) C7 N2 C6 C1 . . . . .1(5) C7 N2 C6 C5 . . . . -179.0(5) H02 N2 C6 C1 . . . . 177(5) H02 N2 C6 C5 . . . . -2(5) C6 N2 C7 N1 . . . . .0(5) C6 N2 C7 C8 . . . . 178.2(4) H02 N2 C7 N1 . . . . -176(5) H02 N2 C7 C8 . . . . 2(5) N1 C1 C2 C3 . . . . -178.4(5) C6 C1 C2 C3 . . . . .4(7) N1 C1 C6 N2 . . . . -.2(5) N1 C1 C6 C5 . . . . 179.0(4) C2 C1 C6 N2 . . . . -179.3(5) C2 C1 C6 C5 . . . . -.1(7) C1 C2 C3 C4 . . . . -1.0(7) C2 C3 C4 C5 . . . . 1.2(8) C3 C4 C5 C6 . . . . -.8(7) C4 C5 C6 N2 . . . . 179.3(5) C4 C5 C6 C1 . . . . .2(7) N1 C7 C8 O1 . . . . 151.8(4) N1 C7 C8 C8 . . . 2_656 -91.5(5) N2 C7 C8 O1 . . . . -26.0(6) N2 C7 C8 C8 . . . 2_656 90.6(5) 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_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O1 H101 Cl . . 3_445 0.82(2) 2.27(2) 3.068(3) 165(3) N1 H01 O1w . . 1_565 0.85(3) 1.96(3) 2.808(5) 170(5) N2 H02 O1w . . . 0.86(3) 1.97(3) 2.815(5) 170(5) O1w H11w Cl . . 1_545 0.86(2) 2.23(2) 3.084(3) 172(5) O1w H12w Cl . . 2_646 0.85(3) 2.31(3) 3.142(3) 169(5) #=END============================================================== # Attachment 'verdan-2.cif' data_verdan-2 _database_code_depnum_ccdc_archive 'CCDC 683799' #---[RR,SS-1H2]Cl2.EtOH.H2O ----------------------------------------- _audit_creation_date 2007-05-11 _audit_creation_method from_xtal_archive_file_using_CIFIO _audit_update_record 2007-09-10 _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.0.1 _chemical_formula_moiety 'C16 H16 N4 O2 , C2 H6 O , H2 O , 2(Cl)' _chemical_formula_sum 'C18 H24 Cl2 N4 O4' _chemical_formula_weight 431.4 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,-y,-z _cell_length_a 8.0790(5) _cell_length_b 8.2010(6) _cell_length_c 16.3774(13) _cell_angle_alpha 84.534(9) _cell_angle_beta 84.929(9) _cell_angle_gamma 71.783(8) _cell_volume 1024.05(14) _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_meas not_measured _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 28.5 _cell_measurement_temperature 150 _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu .35 _exptl_crystal_description prism _exptl_crystal_size_max .26 _exptl_crystal_size_mid .24 _exptl_crystal_size_min .11 _exptl_crystal_colour colorless _diffrn_measurement_device_type 'Stoe Ipds' _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 6 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'XRED; Stoe & Cie, 1999' _exptl_absorpt_correction_T_min .9219 _exptl_absorpt_correction_T_max .9689 _diffrn_reflns_number 12392 _reflns_number_total 5049 _reflns_number_gt 3326 _reflns_threshold_expression 'refl observed if Fo > 3.99 \s(Fo)' _diffrn_reflns_theta_max 28.5 _diffrn_reflns_theta_full 28.5 _diffrn_measured_fraction_theta_max 1.0 _diffrn_measured_fraction_theta_full 1.0 _diffrn_reflns_av_R_equivalents .033 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_standards_decay_% 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .036 _refine_ls_wR_factor_ref .036 _refine_ls_goodness_of_fit_ref 1.45(2) _refine_ls_number_reflns 3392 _refine_ls_number_parameters 280 _refine_ls_weighting_scheme calc _refine_ls_weighting_details \w=1/[\s^2^(Fo)+0.0002(Fo^2^)] _refine_ls_hydrogen_treatment mixed _refine_ls_shift/su_max .003 _refine_diff_density_max .563 _refine_diff_density_min -.61 _refine_ls_extinction_method none _refine_ls_extinction_coef .00000 _refine_ls_abs_structure_details none _computing_data_collection 'EXPOSE (Stoe & Cie, 1999)' _computing_cell_refinement 'CELL (Stoe & Cie, 1999)' _computing_data_reduction 'XRED (Stoe & Cie, 1999)' _computing_structure_solution SIR97 _computing_structure_refinement xtal_CRYLSQ _computing_molecular_graphics xtal_gx3 _computing_publication_material xtal_CIFIO loop_ _atom_type_symbol _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .002 .002 H Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 0 0 N Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .004 .003 O Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .008 .006 Cl Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .132 .159 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 .52754(19) .52089(15) .24730(8) .0208(10) 1.00000 Uani O2 .20494(19) .46426(16) .29177(9) .0255(10) 1.00000 Uani N1 .3534(3) .60985(18) .10952(9) .0186(11) 1.00000 Uani N2 .3538(3) .35133(19) .08868(9) .0193(11) 1.00000 Uani N3 .5813(3) .12883(18) .37322(9) .0181(11) 1.00000 Uani N4 .3890(3) .34488(18) .43042(9) .0181(11) 1.00000 Uani C1 .2722(3) .6241(3) .03666(11) .0189(12) 1.00000 Uani C2 .1971(3) .7658(3) -.01736(12) .0275(14) 1.00000 Uani C3 .1254(3) .7316(3) -.08513(12) .0311(16) 1.00000 Uani C4 .1303(3) .5641(3) -.09985(12) .0280(15) 1.00000 Uani C5 .2051(3) .4236(3) -.04673(12) .0246(14) 1.00000 Uani C6 .2739(3) .4585(3) .02271(11) .0186(12) 1.00000 Uani C7 .4002(3) .4461(2) .13910(10) .0162(12) 1.00000 Uani C8 .4853(3) .3834(2) .21868(11) .0171(12) 1.00000 Uani C9 .3557(3) .3234(3) .28099(11) .0184(12) 1.00000 Uani C10 .4415(3) .2649(3) .36108(11) .0173(12) 1.00000 Uani C11 .6243(3) .1191(3) .45441(11) .0187(12) 1.00000 Uani C12 .7576(3) .0027(3) .49853(12) .0225(13) 1.00000 Uani C13 .7591(3) .0305(3) .58066(12) .0258(14) 1.00000 Uani C14 .6331(3) .1681(3) .61777(11) .0262(14) 1.00000 Uani C15 .5004(3) .2836(3) .57411(11) .0225(13) 1.00000 Uani C16 .5006(3) .2560(2) .49134(11) .0182(12) 1.00000 Uani Cl1 .11977(7) .65228(6) .67657(3) .0263(4) 1.00000 Uani Cl2 .60945(9) .03090(6) .86463(4) .0383(5) 1.00000 Uani O1a .3041(3) .0550(3) .76020(12) .0515(15) 1.00000 Uani C1a .1366(4) .1619(3) .78439(14) .0363(17) 1.00000 Uani C2a .0070(4) .1325(3) .73171(16) .0437(19) 1.00000 Uani O1w .8907(3) .3901(2) .51088(10) .0383(12) 1.00000 Uani H01 .368(4) .696(4) .1318(17) .05000 1.00000 Uiso H02 .369(4) .240(4) .0977(16) .05000 1.00000 Uiso H03 .635(4) .054(4) .3378(18) .05000 1.00000 Uiso H04 .305(4) .436(4) .4346(17) .05000 1.00000 Uiso H001 .623(5) .484(4) .2640(18) .05000 1.00000 Uiso H002 .115(5) .436(4) .2994(17) .05000 1.00000 Uiso H2 .19523 .88247 -.00780 .05000 1.00000 Uiso H3 .06930 .82734 -.12399 .05000 1.00000 Uiso H4 .07960 .54615 -.14907 .05000 1.00000 Uiso H5 .20937 .30664 -.05723 .05000 1.00000 Uiso H8 .59162 .28574 .21170 .05000 1.00000 Uiso H9 .32425 .22863 .26119 .05000 1.00000 Uiso H12 .84538 -.09342 .47280 .05000 1.00000 Uiso H13 .85051 -.04767 .61380 .05000 1.00000 Uiso H14 .63923 .18257 .67605 .05000 1.00000 Uiso H15 .41175 .37889 .59986 .05000 1.00000 Uiso H11a .10792 .13340 .84226 .05000 1.00000 Uiso H12a .13368 .28277 .77686 .05000 1.00000 Uiso H21a .03595 .16096 .67387 .05000 1.00000 Uiso H22a .01020 .01159 .73927 .05000 1.00000 Uiso H23a -.10921 .20675 .74854 .05000 1.00000 Uiso H01a .374(3) .068(3) .7869(14) .05000 1.00000 Uiso H11w .873(4) .361(3) .4632(14) .05000 1.00000 Uiso H12w .870(4) .323(3) .5466(11) .05000 1.00000 Uiso 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 .0199(9) .0216(6) .0243(7) -.0098(6) -.0047(6) -.0028(5) O2 .0141(9) .0254(7) .0347(8) -.0038(6) .0003(6) -.0003(6) N1 .0205(10) .0159(7) .0202(8) -.0065(6) -.0024(6) -.0019(6) N2 .0226(10) .0156(7) .0207(8) -.0067(6) -.0028(7) -.0024(6) N3 .0181(10) .0171(7) .0193(8) -.0058(6) .0004(6) -.0022(6) N4 .0194(10) .0167(7) .0184(8) -.0061(6) -.0000(7) -.0019(6) C1 .0158(11) .0219(8) .0188(9) -.0063(7) .0000(7) -.0002(7) C2 .0291(13) .0233(9) .0287(10) -.0077(8) -.0043(9) .0068(8) C3 .0263(13) .0382(11) .0253(11) -.0075(9) -.0043(9) .0088(9) C4 .0212(12) .0456(11) .0179(9) -.0114(9) -.0017(8) -.0012(8) C5 .0242(12) .0320(10) .0205(10) -.0118(8) .0004(8) -.0062(8) C6 .0156(11) .0210(8) .0182(8) -.0052(7) .0019(7) -.0006(7) C7 .0140(11) .0173(8) .0178(8) -.0060(7) .0022(7) -.0028(6) C8 .0157(11) .0163(7) .0195(9) -.0053(7) -.0002(7) -.0019(6) C9 .0175(11) .0192(8) .0195(9) -.0072(7) -.0016(7) -.0017(7) C10 .0172(11) .0177(8) .0195(9) -.0093(7) .0013(7) -.0019(7) C11 .0207(11) .0195(8) .0189(9) -.0109(7) .0004(7) -.0010(7) C12 .0219(12) .0204(8) .0256(10) -.0077(8) -.0015(8) .0002(7) C13 .0265(13) .0265(9) .0266(10) -.0121(8) -.0062(9) .0057(8) C14 .0330(13) .0301(10) .0194(9) -.0156(9) -.0040(8) .0007(8) C15 .0268(12) .0222(8) .0206(9) -.0105(8) .0006(8) -.0032(7) C16 .0186(11) .0166(8) .0215(9) -.0089(7) -.0002(7) -.0002(7) Cl1 .0198(3) .0301(3) .0296(3) -.00912(19) -.00470(19) .00186(18) Cl2 .0546(4) .0175(3) .0486(4) -.0155(3) -.0218(3) .0019(2) O1a .0298(11) .0718(12) .0511(11) -.0012(9) -.0061(8) -.0414(9) C1a .0382(15) .0296(10) .0400(13) -.0068(10) .0013(10) -.0141(9) C2a .0373(16) .0377(12) .0526(15) -.0020(10) -.0087(12) -.0135(11) O1w .0370(11) .0360(8) .0330(9) .0042(7) -.0035(7) -.0107(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance O1 C8 . . 1.406(3) O1 H001 . . .80(4) O2 C9 . . 1.404(2) O2 H002 . . .82(4) N1 C1 . . 1.390(3) N1 C7 . . 1.331(2) N1 H01 . . .87(4) N2 C6 . . 1.394(3) N2 C7 . . 1.337(3) N2 H02 . . .88(3) N3 C10 . . 1.330(2) N3 C11 . . 1.393(3) N3 H03 . . .87(3) N4 C10 . . 1.335(3) N4 C16 . . 1.396(3) N4 H04 . . .84(3) C1 C2 . . 1.400(3) C1 C6 . . 1.394(3) C2 C3 . . 1.386(4) C3 C4 . . 1.405(4) C4 C5 . . 1.384(3) C5 C6 . . 1.399(3) C7 C8 . . 1.498(3) C8 C9 . . 1.555(3) C9 C10 . . 1.505(3) C11 C12 . . 1.399(3) C11 C16 . . 1.395(3) C12 C13 . . 1.387(3) C13 C14 . . 1.408(3) C14 C15 . . 1.389(3) C15 C16 . . 1.395(3) O1a C1a . . 1.410(3) O1a H01a . . .78(3) C1a C2a . . 1.502(5) O1w H11w . . .87(3) O1w H12w . . .81(4) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle C8 O1 H001 . . . 108(3) C9 O2 H002 . . . 112.7(18) C1 N1 C7 . . . 109.04(16) C1 N1 H01 . . . 124.3(17) C7 N1 H01 . . . 126.6(17) C6 N2 C7 . . . 108.74(15) C6 N2 H02 . . . 126.8(19) C7 N2 H02 . . . 124.4(19) C10 N3 C11 . . . 108.67(14) C10 N3 H03 . . . 126.5(19) C11 N3 H03 . . . 124.7(18) C10 N4 C16 . . . 108.50(13) C10 N4 H04 . . . 124(2) C16 N4 H04 . . . 127(2) N1 C1 C2 . . . 132.00(18) N1 C1 C6 . . . 106.44(14) C2 C1 C6 . . . 121.55(18) C1 C2 C3 . . . 116.16(19) C2 C3 C4 . . . 122.12(18) C3 C4 C5 . . . 121.9(2) C4 C5 C6 . . . 116.05(19) N2 C6 C1 . . . 106.28(16) N2 C6 C5 . . . 131.51(17) C1 C6 C5 . . . 122.21(15) N1 C7 N2 . . . 109.49(15) N1 C7 C8 . . . 124.01(17) N2 C7 C8 . . . 126.46(15) O1 C8 C7 . . . 107.61(13) O1 C8 C9 . . . 110.91(14) C7 C8 C9 . . . 108.96(16) O2 C9 C8 . . . 108.00(13) O2 C9 C10 . . . 110.16(14) C8 C9 C10 . . . 108.24(16) N3 C10 N4 . . . 110.01(15) N3 C10 C9 . . . 125.50(15) N4 C10 C9 . . . 124.49(14) N3 C11 C12 . . . 132.01(15) N3 C11 C16 . . . 106.51(14) C12 C11 C16 . . . 121.47(16) C11 C12 C13 . . . 116.42(16) C12 C13 C14 . . . 121.86(17) C13 C14 C15 . . . 121.81(18) C14 C15 C16 . . . 116.05(15) N4 C16 C11 . . . 106.31(15) N4 C16 C15 . . . 131.31(15) C11 C16 C15 . . . 122.37(15) C1a O1a H01a . . . 110.3(14) O1a C1a C2a . . . 108.28(19) H11w O1w H12w . . . 109(3) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion H001 O1 C8 C7 . . . . -137(3) H001 O1 C8 C9 . . . . 104(3) H002 O2 C9 C8 . . . . 146(3) H002 O2 C9 C10 . . . . -96(3) C7 N1 C1 C2 . . . . 178.7(3) C7 N1 C1 C6 . . . . -.7(2) H01 N1 C1 C2 . . . . 0(3) H01 N1 C1 C6 . . . . -180(3) C1 N1 C7 N2 . . . . .2(3) C1 N1 C7 C8 . . . . -177.59(17) H01 N1 C7 N2 . . . . 179(3) H01 N1 C7 C8 . . . . 1(3) C7 N2 C6 C1 . . . . -.8(2) C7 N2 C6 C5 . . . . 178.9(2) H02 N2 C6 C1 . . . . 177(3) H02 N2 C6 C5 . . . . -3(3) C6 N2 C7 N1 . . . . .4(3) C6 N2 C7 C8 . . . . 178.11(17) H02 N2 C7 N1 . . . . -178(3) H02 N2 C7 C8 . . . . 0(3) C11 N3 C10 N4 . . . . -.5(3) C11 N3 C10 C9 . . . . 178.48(19) H03 N3 C10 N4 . . . . 177(3) H03 N3 C10 C9 . . . . -4(3) C10 N3 C11 C12 . . . . 180.0(3) C10 N3 C11 C16 . . . . .9(3) H03 N3 C11 C12 . . . . 3(3) H03 N3 C11 C16 . . . . -176(3) C16 N4 C10 N3 . . . . -.1(3) C16 N4 C10 C9 . . . . -179.10(19) H04 N4 C10 N3 . . . . 178(3) H04 N4 C10 C9 . . . . -1(3) C10 N4 C16 C11 . . . . .7(3) C10 N4 C16 C15 . . . . -178.3(3) H04 N4 C16 C11 . . . . -177(3) H04 N4 C16 C15 . . . . 4(3) N1 C1 C2 C3 . . . . -179.5(2) C6 C1 C2 C3 . . . . -.2(3) N1 C1 C6 N2 . . . . .9(2) N1 C1 C6 C5 . . . . -178.82(17) C2 C1 C6 N2 . . . . -178.56(18) C2 C1 C6 C5 . . . . 1.7(3) C1 C2 C3 C4 . . . . -1.1(4) C2 C3 C4 C5 . . . . 1.0(4) C3 C4 C5 C6 . . . . .5(3) C4 C5 C6 N2 . . . . 178.5(2) C4 C5 C6 C1 . . . . -1.8(3) N1 C7 C8 O1 . . . . -8.6(3) N1 C7 C8 C9 . . . . 111.70(19) N2 C7 C8 O1 . . . . 174.02(17) N2 C7 C8 C9 . . . . -65.7(3) O1 C8 C9 O2 . . . . 58.87(19) O1 C8 C9 C10 . . . . -60.38(16) C7 C8 C9 O2 . . . . -59.40(19) C7 C8 C9 C10 . . . . -178.65(13) O2 C9 C10 N3 . . . . 176.06(19) O2 C9 C10 N4 . . . . -5.1(3) C8 C9 C10 N3 . . . . -66.1(3) C8 C9 C10 N4 . . . . 112.8(2) N3 C11 C12 C13 . . . . -178.6(3) C16 C11 C12 C13 . . . . .4(4) N3 C11 C16 N4 . . . . -.9(3) N3 C11 C16 C15 . . . . 178.2(2) C12 C11 C16 N4 . . . . 179.9(2) C12 C11 C16 C15 . . . . -1.0(4) C11 C12 C13 C14 . . . . .1(4) C12 C13 C14 C15 . . . . -.0(4) C13 C14 C15 C16 . . . . -.6(4) C14 C15 C16 N4 . . . . 179.9(3) C14 C15 C16 C11 . . . . 1.1(4) H01a O1a C1a C2a . . . . -179.7(18) 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_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O1 H001 Cl1 . . 2_666 0.80(3) 2.28(3) 3.074(1) 171(3) O2 H002 Cl1 . . 2_566 0.82(4) 2.23(4) 3.049(2) 177(2) N1 H01 Cl2 . . 2_666 0.87(3) 2.31(3) 3.124(2) 156(2) N2 H02 Cl2 . . 2_656 0.88(3) 2.20(3) 3.082(2) 173(2) N3 H03 O1a . . 2_656 0.87(3) 1.87(3) 2.702(2) 161(3) N4 H04 O1w . . 2_666 0.84(3) 1.98(3) 2.775(2) 158(3) O1a H01a Cl2 . . . 0.78(2) 2.31(2) 3.070(2) 166(2) O1w H11w Cl1 . . 2_666 0.87(2) 2.30(2) 3.134(2) 160(3) #=END====================================================================== # Attachment 'verdan-3.cif' data_verdan-3 _database_code_depnum_ccdc_archive 'CCDC 683800' #----- [S-3H2]Cl2.2H2O ----------------------------------------------- _audit_creation_date 2006-11-10 _audit_creation_method from_xtal_archive_file_using_CIFIO _audit_update_record 2007-09-19 _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.0.1 _chemical_formula_moiety 'C16 H16 N4 O , (H2 O)2 , 2Cl' _chemical_formula_sum 'C16 H20 Cl2 N4 O3' _chemical_formula_weight 387.3 _chemical_absolute_configuration rmad _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'p 2yb' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,1/2+y,-z _cell_length_a 8.5668(9) _cell_length_b 12.2524(11) _cell_length_c 9.3375(10) _cell_angle_alpha 90.00000 _cell_angle_beta 103.982(12) _cell_angle_gamma 90.00000 _cell_volume 951.06(17) _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_meas not_measured _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _cell_measurement_reflns_used 6672 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 26.8 _cell_measurement_temperature 220 _exptl_absorpt_coefficient_mu .363 _exptl_crystal_F_000 404 _exptl_crystal_description prism _exptl_crystal_size_max .25 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .11 _exptl_crystal_colour colorless _diffrn_measurement_device_type 'Stoe Ipds' _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 6 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'XRED; Stoe & Cie, 1999' _exptl_absorpt_correction_T_min .9416 _exptl_absorpt_correction_T_max .9665 _diffrn_reflns_number 11939 _reflns_number_total 4114 _reflns_number_gt 2169 _reflns_threshold_expression 'refl observed if Fo > 3.99 \s(Fo)' _diffrn_reflns_theta_max 26.8 _diffrn_reflns_theta_full 26.8 _diffrn_reflns_av_R_equivalents .061 _diffrn_measured_fraction_theta_max 1.0 _diffrn_measured_fraction_theta_full 1.0 _reflns_Friedel_coverage .951 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_standards_decay_% 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .043 _refine_ls_wR_factor_ref .042 _refine_ls_goodness_of_fit_ref 1.49(2) _refine_ls_number_reflns 2169 _refine_ls_number_parameters 241 _refine_ls_weighting_scheme calc _refine_ls_weighting_details \w=1/[\s^2^(Fo)+0.0005(Fo^2^)] _refine_ls_hydrogen_treatment mixed _refine_ls_shift/su_max .004 _refine_diff_density_max .825 _refine_diff_density_min -.508 _refine_ls_extinction_method none _refine_ls_abs_structure_details Flack_xabs_refined _refine_ls_abs_structure_Flack .03(19) _refine_special_details ; Hydrogen treatment: - Hydrogen atoms of water molecules and -OH group were observed and refined with restraints on bond lengths and bond angles. - Coordinates of other H atoms were calculated. Definition of polar origin: y(Cl1) = fixed as a hard constraint ; _computing_data_collection 'EXPOSE (Stoe & Cie, 1999)' _computing_cell_refinement 'CELL (Stoe & Cie, 1999)' _computing_data_reduction 'XRED (Stoe & Cie, 1999)' _computing_structure_solution SIR97 _computing_structure_refinement xtal_CRYLSQ _computing_molecular_graphics xtal_gx3 _computing_publication_material xtal_CIFIO loop_ _atom_type_symbol _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .002 .002 H Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 0 0 N Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .004 .003 O Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .008 .006 Cl Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .132 .159 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type Cl1 -.0822(4) .37500 .1625(3) .0588(14) 1.00000 Uani Cl2 .5816(3) .01801(19) -.1835(3) .0560(14) 1.00000 Uani O1 .2730(7) .1308(6) -.1552(6) .073(4) 1.00000 Uani N1 .0128(10) .3008(7) -.2126(8) .048(5) 1.00000 Uani N2 .1674(9) .4265(7) -.0846(8) .045(5) 1.00000 Uani N3 .3417(10) -.0159(8) .0843(8) .050(5) 1.00000 Uani N4 .5009(10) .1010(8) .2176(8) .049(5) 1.00000 Uani C1 -.0210(11) .4006(10) -.2900(9) .047(6) 1.00000 Uani C2 -.1352(13) .4235(10) -.4201(11) .062(7) 1.00000 Uani C3 -.1406(13) .5312(11) -.4641(10) .066(7) 1.00000 Uani C4 -.0420(14) .6111(12) -.3791(13) .077(8) 1.00000 Uani C5 .0677(14) .5874(10) -.2506(12) .066(7) 1.00000 Uani C6 .0738(11) .4806(10) -.2067(10) .050(6) 1.00000 Uani C7 .1257(11) .3228(8) -.0922(9) .042(5) 1.00000 Uani C8 .1987(11) .2365(10) .0239(9) .053(5) 1.00000 Uani C9 .3314(12) .1723(9) -.0180(9) .050(5) 1.00000 Uani C10 .3900(12) .0890(9) .0940(10) .048(6) 1.00000 Uani C11 .4270(12) -.0743(8) .2071(10) .044(6) 1.00000 Uani C12 .4302(13) -.1840(10) .2450(10) .056(6) 1.00000 Uani C13 .5333(15) -.2131(9) .3749(12) .068(7) 1.00000 Uani C14 .6345(16) -.1391(13) .4618(11) .081(9) 1.00000 Uani C15 .6377(14) -.0275(9) .4247(11) .058(7) 1.00000 Uani C16 .5339(11) .0016(10) .2932(9) .045(5) 1.00000 Uani O1w -.1049(9) .0995(7) -.2740(9) .067(5) 1.00000 Uani O2w .6255(9) .3022(6) .2762(8) .063(4) 1.00000 Uani H01 -.03127 .22907 -.24412 .05000 1.00000 Uiso H02 .24762 .45984 -.00763 .05000 1.00000 Uiso H03 .25612 -.04677 .00221 .05000 1.00000 Uiso H04 .56065 .17065 .25224 .05000 1.00000 Uiso H2 -.20226 .35895 -.47738 .05000 1.00000 Uiso H3 -.21304 .54891 -.55645 .05000 1.00000 Uiso H4 -.05367 .68905 -.40929 .05000 1.00000 Uiso H5 .13856 .64255 -.18836 .05000 1.00000 Uiso H12 .36271 -.23871 .18644 .05000 1.00000 Uiso H13 .52808 -.28719 .41224 .05000 1.00000 Uiso H14 .70846 -.16900 .55229 .05000 1.00000 Uiso H15 .70950 .02087 .48743 .05000 1.00000 Uiso H81 .23745 .27388 .11891 .05000 1.00000 Uiso H82 .11181 .18475 .03465 .05000 1.00000 Uiso H9 .42455 .22170 -.01748 .05000 1.00000 Uiso H101 .346(5) .084(5) -.177(4) .05000 1.00000 Uiso H11w -.037(6) .043(4) -.261(8) .05000 1.00000 Uiso H12w -.187(6) .085(5) -.232(7) .05000 1.00000 Uiso H21w .556(5) .328(6) .197(5) .05000 1.00000 Uiso H22w .725(4) .318(6) .271(6) .05000 1.00000 Uiso 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 Cl1 .0526(15) .0468(16) .0775(15) .0137(12) .0166(12) .0139(13) Cl2 .0484(14) .0506(17) .0697(13) .0066(13) .0157(11) .0080(13) O1 .069(4) .071(5) .076(4) .010(4) .011(3) -.012(4) N1 .054(5) .041(6) .050(5) -.008(4) .012(4) -.006(4) N2 .043(5) .028(5) .061(5) -.002(4) .009(4) -.001(4) N3 .048(5) .053(6) .047(4) .002(4) .008(4) -.005(4) N4 .055(5) .038(6) .052(5) -.003(5) .009(4) .002(4) C1 .046(6) .054(7) .046(5) .018(6) .023(5) .010(5) C2 .060(7) .072(10) .053(6) -.004(7) .010(5) .001(6) C3 .067(7) .064(9) .058(6) .029(7) -.002(5) .013(6) C4 .071(8) .067(9) .094(8) .037(7) .020(7) .044(7) C5 .072(8) .035(7) .091(8) .009(6) .020(7) -.008(6) C6 .037(6) .067(9) .048(5) -.015(6) .013(4) .001(6) C7 .045(5) .032(6) .049(5) .003(4) .014(4) .006(4) C8 .061(6) .046(6) .054(5) .002(5) .015(4) .001(5) C9 .048(5) .059(7) .043(5) .008(5) .012(4) -.001(5) C10 .047(6) .041(6) .058(6) -.006(5) .017(5) -.013(5) C11 .056(7) .023(6) .057(6) .011(5) .022(5) -.001(5) C12 .066(7) .053(7) .055(6) -.011(6) .027(6) .006(5) C13 .102(10) .045(7) .066(6) -.003(6) .039(6) -.004(6) C14 .106(10) .090(12) .051(6) .018(9) .028(6) .021(7) C15 .060(7) .061(9) .047(6) .008(6) .003(5) -.009(5) C16 .048(6) .039(6) .048(5) -.015(5) .012(4) -.006(5) O1w .049(5) .047(5) .104(5) -.004(4) .019(4) .004(4) O2w .047(4) .050(5) .090(5) -.011(4) .014(4) -.014(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance O1 C9 . . 1.357(10) N1 C1 . . 1.414(14) N1 C7 . . 1.322(10) N2 C6 . . 1.393(12) N2 C7 . . 1.317(13) N3 C10 . . 1.346(14) N3 C11 . . 1.399(11) N4 C10 . . 1.313(11) N4 C16 . . 1.401(14) C1 C2 . . 1.392(12) C1 C6 . . 1.386(14) C2 C3 . . 1.379(18) C3 C4 . . 1.407(17) C4 C5 . . 1.364(15) C5 C6 . . 1.368(16) C7 C8 . . 1.536(13) C8 C9 . . 1.509(15) C9 C10 . . 1.461(14) C11 C12 . . 1.388(15) C11 C16 . . 1.413(13) C12 C13 . . 1.364(14) C13 C14 . . 1.375(17) C14 C15 . . 1.413(19) C15 C16 . . 1.377(12) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle C1 N1 C7 . . . 106.0(8) C6 N2 C7 . . . 108.7(8) C10 N3 C11 . . . 110.0(7) C10 N4 C16 . . . 111.2(9) N1 C1 C2 . . . 129.4(10) N1 C1 C6 . . . 107.8(7) C2 C1 C6 . . . 122.7(11) C1 C2 C3 . . . 114.8(10) C2 C3 C4 . . . 121.7(9) C3 C4 C5 . . . 122.7(12) C4 C5 C6 . . . 115.8(10) N2 C6 C1 . . . 105.4(9) N2 C6 C5 . . . 132.3(9) C1 C6 C5 . . . 122.2(9) N1 C7 N2 . . . 112.1(8) N1 C7 C8 . . . 123.3(9) N2 C7 C8 . . . 124.6(8) C7 C8 C9 . . . 112.3(8) O1 C9 C8 . . . 108.1(7) O1 C9 C10 . . . 113.5(9) C8 C9 C10 . . . 109.1(9) N3 C10 N4 . . . 108.1(9) N3 C10 C9 . . . 124.9(8) N4 C10 C9 . . . 127.0(10) N3 C11 C12 . . . 132.7(8) N3 C11 C16 . . . 105.5(8) C12 C11 C16 . . . 121.5(8) C11 C12 C13 . . . 116.6(10) C12 C13 C14 . . . 122.2(11) C13 C14 C15 . . . 122.7(10) C14 C15 C16 . . . 115.0(10) N4 C16 C11 . . . 105.1(7) N4 C16 C15 . . . 133.0(10) C11 C16 C15 . . . 121.8(10) 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion C7 N1 C1 C2 . . . . -176.9(11) C7 N1 C1 C6 . . . . -1.6(11) C1 N1 C7 N2 . . . . .0(12) C1 N1 C7 C8 . . . . -179.8(9) C7 N2 C6 C1 . . . . -2.5(11) C7 N2 C6 C5 . . . . 179.3(12) C6 N2 C7 N1 . . . . 1.6(12) C6 N2 C7 C8 . . . . -178.6(9) C11 N3 C10 N4 . . . . -.6(12) C11 N3 C10 C9 . . . . 177.3(10) C10 N3 C11 C12 . . . . -175.3(12) C10 N3 C11 C16 . . . . -.8(12) C16 N4 C10 N3 . . . . 1.8(12) C16 N4 C10 C9 . . . . -176.0(10) C10 N4 C16 C11 . . . . -2.3(12) C10 N4 C16 C15 . . . . -179.8(12) N1 C1 C2 C3 . . . . 178.0(11) C6 C1 C2 C3 . . . . 3.3(16) N1 C1 C6 N2 . . . . 2.5(11) N1 C1 C6 C5 . . . . -179.1(10) C2 C1 C6 N2 . . . . 178.2(10) C2 C1 C6 C5 . . . . -3.4(17) C1 C2 C3 C4 . . . . -2.5(17) C2 C3 C4 C5 . . . . 2(2) C3 C4 C5 C6 . . . . -1.5(19) C4 C5 C6 N2 . . . . -179.8(12) C4 C5 C6 C1 . . . . 2.3(17) N1 C7 C8 C9 . . . . 83.1(12) N2 C7 C8 C9 . . . . -96.8(12) C7 C8 C9 O1 . . . . -53.7(11) C7 C8 C9 C10 . . . . -177.6(8) O1 C9 C10 N3 . . . . -24.1(15) O1 C9 C10 N4 . . . . 153.3(10) C8 C9 C10 N3 . . . . 96.6(12) C8 C9 C10 N4 . . . . -86.0(13) N3 C11 C12 C13 . . . . 178.3(12) C16 C11 C12 C13 . . . . 4.6(17) N3 C11 C16 N4 . . . . 1.8(11) N3 C11 C16 C15 . . . . 179.6(10) C12 C11 C16 N4 . . . . 177.0(10) C12 C11 C16 C15 . . . . -5.1(16) C11 C12 C13 C14 . . . . -2.6(19) C12 C13 C14 C15 . . . . 0(3) C13 C14 C15 C16 . . . . -1.2(19) C14 C15 C16 N4 . . . . -179.7(11) C14 C15 C16 C11 . . . . 3.2(16) 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_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O1 H101 Cl2 . . . 0.92(5) 2.19(4) 3.051(7) 158(4) N1 H01 O1w . . . 0.97 1.71 2.673(11) 172 N2 H02 Cl2 . . 2_655 0.96 2.14 3.090(7) 172 N3 H03 Cl1 . . 2_545 1.00 2.10 3.092(7) 175 N4 H04 O2w . . . 1.01 1.70 2.690(11) 166 O1w H11w Cl1 . . 2_545 0.90(5) 2.38(4) 3.227(8) 158(6) O1w H12w Cl2 . . 1_455 0.90(6) 2.29(5) 3.165(9) 164(5) O2w H21w Cl2 . . 2_655 0.89(4) 2.60(6) 3.185(7) 125(5) O2w H22w Cl1 . . 1_655 0.89(4) 2.24(5) 3.079(8) 156(5) #==END============================================================== # Attachment 'verdan-4.cif' data_verdan-4 _database_code_depnum_ccdc_archive 'CCDC 683801' #---- [4] ----------------------------------------------------------- _audit_creation_date 2005-11-08 _audit_creation_method from_xtal_archive_file_using_CIFIO _audit_update_record 2007-09-19 _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.0.1 _chemical_formula_moiety 'C10 H10 N2 O2' _chemical_formula_sum 'C10 H10 N2 O2' _chemical_formula_weight 190.2 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,1/2+y,1/2-z -x,-y,-z +x,1/2-y,1/2+z _cell_length_a 16.1313(16) _cell_length_b 5.0524(4) _cell_length_c 11.8012(13) _cell_angle_alpha 90.00000 _cell_angle_beta 109.906(11) _cell_angle_gamma 90.00000 _cell_volume 904.35(16) _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_meas not_measured _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _cell_measurement_reflns_used 4293 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 26.6 _cell_measurement_temperature 200 _exptl_absorpt_coefficient_mu .10 _exptl_crystal_F_000 400 _exptl_crystal_description 'hexagonal prism' _exptl_crystal_size_max .24 _exptl_crystal_size_mid .17 _exptl_crystal_size_min .13 _exptl_crystal_colour colorless _diffrn_measurement_device_type 'Stoe Ipds' _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 6 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'XRED; Stoe & Cie, 1999' _exptl_absorpt_correction_T_min .9808 _exptl_absorpt_correction_T_max .9895 _diffrn_reflns_number 8753 _reflns_number_total 1886 _reflns_number_gt 1054 _reflns_threshold_expression 'refl observed if Fo > 3.99 \s(Fo)' _diffrn_reflns_theta_max 26.6 _diffrn_reflns_theta_full 26.6 _diffrn_measured_fraction_theta_max 1.0 _diffrn_measured_fraction_theta_full 1.0 _diffrn_reflns_av_R_equivalents .058 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_standards_decay_% 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .032 _refine_ls_wR_factor_ref .032 _refine_ls_goodness_of_fit_ref 1.21(3) _refine_ls_number_reflns 1112 _refine_ls_number_parameters 133 _refine_ls_weighting_scheme calc _refine_ls_weighting_details \w=1/[\s^2^(Fo)+0.0003(Fo^2^)] _refine_ls_hydrogen_treatment mixed _refine_ls_shift/su_max .00027 _refine_diff_density_max .418 _refine_diff_density_min -.522 _refine_ls_extinction_method none _refine_ls_abs_structure_details none _computing_data_collection 'EXPOSE (Stoe & Cie, 1999)' _computing_cell_refinement 'CELL (Stoe & Cie, 1999)' _computing_data_reduction 'XRED (Stoe & Cie, 1999)' _computing_structure_solution SIR97 _computing_structure_refinement xtal_CRYLSQ _computing_molecular_graphics xtal_gx3 _computing_publication_material xtal_CIFIO loop_ _atom_type_symbol _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .002 .002 H Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 0 0 N Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .004 .003 O Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .008 .006 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 .80782(10) 1.2170(3) .17663(12) .0357(8) 1.00000 Uani O2 .87699(9) 1.1419(3) .04551(11) .0308(7) 1.00000 Uani N1 .76963(11) .6196(3) .29989(13) .0242(8) 1.00000 Uani N2 .78991(11) .9491(3) .42667(13) .0236(8) 1.00000 Uani C1 .69626(13) .6243(4) .33638(16) .0243(9) 1.00000 Uani C2 .62114(14) .4670(4) .30561(18) .0302(10) 1.00000 Uani C3 .56058(15) .5268(4) .36120(19) .0350(11) 1.00000 Uani C4 .57383(15) .7339(5) .44356(19) .0348(11) 1.00000 Uani C5 .64829(14) .8936(4) .47343(17) .0300(10) 1.00000 Uani C6 .70977(13) .8348(4) .41775(15) .0228(9) 1.00000 Uani C7 .82441(13) .8137(4) .35621(15) .0225(9) 1.00000 Uani C8 .91228(13) .8631(4) .34639(16) .0248(9) 1.00000 Uani C9 .91251(13) .8638(4) .21704(16) .0230(9) 1.00000 Uani C10 .86162(13) 1.0930(4) .14114(16) .0219(9) 1.00000 Uani H2 .61123 .32487 .24669 .04000 1.00000 Uiso H3 .50693 .41790 .34264 .04000 1.00000 Uiso H4 .52937 .76987 .48138 .04000 1.00000 Uiso H5 .65675 1.04059 .53047 .04000 1.00000 Uiso H81 .93370 1.03579 .38233 .04000 1.00000 Uiso H82 .95294 .72436 .39097 .04000 1.00000 Uiso H91 .97383 .87383 .21943 .04000 1.00000 Uiso H92 .88610 .69787 .17844 .04000 1.00000 Uiso H01 .7841(15) .491(5) .255(2) .04000 1.00000 Uiso H02 .8218(15) 1.106(4) .4733(19) .04000 1.00000 Uiso 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 .0476(10) .0293(8) .0340(8) .0140(7) .0189(7) -.0004(6) O2 .0364(9) .0323(8) .0270(7) .0050(6) .0151(7) .0079(6) N1 .0283(11) .0228(8) .0223(8) .0010(7) .0098(8) -.0028(7) N2 .0279(11) .0236(8) .0206(8) .0003(7) .0100(7) -.0006(7) C1 .0269(12) .0246(9) .0223(9) .0039(9) .0094(9) .0033(8) C2 .0308(13) .0259(10) .0331(11) -.0015(9) .0099(10) .0002(8) C3 .0309(14) .0322(11) .0430(12) -.0025(10) .0141(11) .0061(10) C4 .0325(14) .0378(11) .0401(12) .0057(10) .0202(11) .0083(10) C5 .0370(14) .0288(10) .0271(10) .0054(9) .0148(10) .0021(8) C6 .0272(12) .0210(9) .0204(9) .0036(8) .0083(8) .0039(8) C7 .0259(12) .0227(9) .0174(9) .0025(8) .0053(8) .0024(8) C8 .0238(12) .0280(10) .0214(9) .0011(9) .0064(8) .0011(8) C9 .0240(12) .0221(9) .0239(10) .0003(8) .0096(9) .0002(8) C10 .0243(12) .0192(9) .0219(9) -.0034(7) .0075(9) -.0042(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance O1 C10 . . 1.252(3) O2 C10 . . 1.260(3) N1 C1 . . 1.391(3) N1 C7 . . 1.336(3) N1 H01 . . .92(3) N2 C6 . . 1.387(3) N2 C7 . . 1.336(3) N2 H02 . . 1.00(2) C1 C2 . . 1.390(3) C1 C6 . . 1.399(3) C2 C3 . . 1.383(4) C3 C4 . . 1.394(3) C4 C5 . . 1.389(3) C5 C6 . . 1.396(4) C7 C8 . . 1.482(4) C8 C9 . . 1.528(3) C9 C10 . . 1.522(3) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle C1 N1 C7 . . . 108.79(17) C1 N1 H01 . . . 126.9(15) C7 N1 H01 . . . 123.6(14) C6 N2 C7 . . . 108.33(15) C6 N2 H02 . . . 131.5(15) C7 N2 H02 . . . 120.2(15) N1 C1 C2 . . . 131.89(17) N1 C1 C6 . . . 105.98(16) C2 C1 C6 . . . 122.1(3) C1 C2 C3 . . . 116.43(18) C2 C3 C4 . . . 122.0(2) C3 C4 C5 . . . 121.8(3) C4 C5 C6 . . . 116.66(18) N2 C6 C1 . . . 106.98(18) N2 C6 C5 . . . 132.00(16) C1 C6 C5 . . . 121.02(18) N1 C7 N2 . . . 109.91(19) N1 C7 C8 . . . 124.97(18) N2 C7 C8 . . . 125.07(15) C7 C8 C9 . . . 113.97(14) C8 C9 C10 . . . 113.92(16) O1 C10 O2 . . . 124.86(16) O1 C10 C9 . . . 118.69(18) O2 C10 C9 . . . 116.44(18) 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion C7 N1 C1 C2 . . . . -179.84(18) C7 N1 C1 C6 . . . . .41(18) H01 N1 C1 C2 . . . . -9.6(16) H01 N1 C1 C6 . . . . 170.7(16) C1 N1 C7 N2 . . . . -1.03(19) C1 N1 C7 C8 . . . . 176.27(15) H01 N1 C7 N2 . . . . -171.7(16) H01 N1 C7 C8 . . . . 5.6(17) C7 N2 C6 C1 . . . . -.95(18) C7 N2 C6 C5 . . . . 178.51(18) H02 N2 C6 C1 . . . . 178.0(15) H02 N2 C6 C5 . . . . -2.6(16) C6 N2 C7 N1 . . . . 1.24(18) C6 N2 C7 C8 . . . . -176.06(15) H02 N2 C7 N1 . . . . -177.8(13) H02 N2 C7 C8 . . . . 4.9(13) N1 C1 C2 C3 . . . . 179.32(18) C6 C1 C2 C3 . . . . -1.0(3) N1 C1 C6 N2 . . . . .32(17) N1 C1 C6 C5 . . . . -179.20(15) C2 C1 C6 N2 . . . . -179.45(16) C2 C1 C6 C5 . . . . 1.0(3) C1 C2 C3 C4 . . . . .1(3) C2 C3 C4 C5 . . . . .7(3) C3 C4 C5 C6 . . . . -.6(3) C4 C5 C6 N2 . . . . -179.59(17) C4 C5 C6 C1 . . . . -.2(3) N1 C7 C8 C9 . . . . 47.9(3) N2 C7 C8 C9 . . . . -135.20(17) C7 C8 C9 C10 . . . . 66.81(19) C8 C9 C10 O1 . . . . -17.4(3) C8 C9 C10 O2 . . . . 163.13(15) 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_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H01 O1 . . 1_545 0.92(3) 1.78(3) 2.691(3) 174(3) N2 H02 O2 . . 4_575 1.00(2) 1.62(2) 2.6209(19) 177(3) #====================================================================== # Attachment 'verdan-5.cif' data_verdan-5 _database_code_depnum_ccdc_archive 'CCDC 683802' #------ [RR,SS-5] ---------------------------------------------------- _audit_creation_date 2004-10-18 _audit_creation_method from_xtal_archive_file_using_CIFIO _audit_update_record 2007-09-19 _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.0.1 _chemical_formula_moiety 'C15 H18 N2 O2' _chemical_formula_sum 'C15 H18 N2 O2' _chemical_formula_weight 258.4 _chemical_absolute_configuration syn _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,1/2+y,-z _cell_length_a 11.4467(10) _cell_length_b 9.5194(6) _cell_length_c 13.1539(10) _cell_angle_alpha 90.00000 _cell_angle_beta 108.810(9) _cell_angle_gamma 90.00000 _cell_volume 1356.8(2) _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.265 _exptl_absorpt_coefficient_mu .085 _exptl_crystal_F_000 552 _exptl_crystal_density_meas not_measured _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _cell_measurement_reflns_used 7968 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 26.8 _cell_measurement_temperature 200 _exptl_crystal_description prism _exptl_crystal_size_max .30 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .14 _exptl_crystal_colour colourless _diffrn_measurement_device_type 'Stoe Ipds' _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 6 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'XRED; Stoe & Cie, 1999' _exptl_absorpt_correction_T_min .9799 _exptl_absorpt_correction_T_max .9900 _diffrn_reflns_number 16126 _reflns_number_total 5673 _reflns_number_gt 2897 _reflns_threshold_expression 'refl observed if Fo > 3.99 \s(Fo)' _diffrn_reflns_theta_max 26.8 _diffrn_reflns_theta_full 26.8 _diffrn_measured_fraction_theta_max 1.0 _diffrn_measured_fraction_theta_full 1.0 _diffrn_reflns_av_R_equivalents .059 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_standards_decay_% 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .032 _refine_ls_wR_factor_ref .031 _refine_ls_goodness_of_fit_ref 1.50(2) _refine_ls_number_reflns 2897 _refine_ls_number_parameters 348 _refine_ls_weighting_scheme calc _refine_ls_weighting_details \w=1/[\s^2^(Fo)+0.0002(Fo^2^)] _refine_ls_hydrogen_treatment mixed _refine_ls_shift/su_max .00009 _refine_diff_density_max .466 _refine_diff_density_min -.419 _refine_ls_extinction_method none _refine_ls_extinction_coef .00000 _refine_ls_abs_structure_details Flack_xabs_fixed _refine_ls_abs_structure_Flack .5 _computing_data_collection 'EXPOSE (Stoe & Cie, 1999)' _computing_cell_refinement 'CELL (Stoe & Cie, 1999)' _computing_data_reduction 'XRED (Stoe & Cie, 1999)' _computing_structure_solution SIR97 _computing_structure_refinement xtal_CRYLSQ _computing_molecular_graphics xtal_gx3 _computing_publication_material xtal_CIFIO loop_ _atom_type_symbol _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .002 .002 H Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 0 0 N Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .004 .003 O Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .008 .006 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1a .3613(6) .50000 .1450(6) .045(4) 1.00000 Uani O2a .3247(6) .4120(10) .2894(6) .036(4) 1.00000 Uani N1a .2737(6) .7692(10) .3261(6) .035(4) 1.00000 Uani N2a .2620(6) .6619(9) .4725(6) .029(4) 1.00000 Uani C1a .4534(7) .6186(10) .4239(7) .028(5) 1.00000 Uani C2a .4796(7) .5870(10) .3192(8) .026(5) 1.00000 Uani C3a .6053(7) .5142(12) .3439(8) .037(5) 1.00000 Uani C4a .7073(8) .6021(12) .4180(9) .047(6) 1.00000 Uani C5a .6819(8) .6417(12) .5205(8) .045(6) 1.00000 Uani C6a .5549(8) .7125(11) .4952(8) .036(5) 1.00000 Uani C7a .3299(7) .6821(11) .4055(7) .027(5) 1.00000 Uani C8a .1640(7) .8087(11) .3430(8) .033(5) 1.00000 Uani C9a .0720(8) .9019(12) .2869(8) .043(6) 1.00000 Uani C10a -.0264(8) .9220(13) .3230(9) .048(6) 1.00000 Uani C11a -.0357(8) .8494(13) .4122(9) .050(6) 1.00000 Uani C12a .0537(8) .7566(13) .4685(8) .046(6) 1.00000 Uani C13a .1549(7) .7398(11) .4336(8) .031(5) 1.00000 Uani C14a .2959(9) .5772(13) .5697(9) .052(6) 1.00000 Uani C15a .3813(7) .4966(11) .2410(9) .030(5) 1.00000 Uani O1b .4412(8) .0241(13) .2713(8) .096(6) 1.00000 Uani O2b .2824(7) -.0827(10) .1556(7) .052(5) 1.00000 Uani N1b .1480(6) .2504(10) .1666(6) .030(4) 1.00000 Uani N2b .0017(6) .1553(10) .0287(6) .032(4) 1.00000 Uani C1b .2171(7) .1482(11) .0194(8) .031(5) 1.00000 Uani C2b .3476(7) .1296(11) .0980(8) .033(5) 1.00000 Uani C3b .4378(8) .0953(12) .0365(9) .043(6) 1.00000 Uani C4b .4360(10) .2104(13) -.0437(10) .053(6) 1.00000 Uani C5b .3078(9) .2322(12) -.1216(9) .052(7) 1.00000 Uani C6b .2164(8) .2641(13) -.0623(8) .043(6) 1.00000 Uani C7b .1243(7) .1829(11) .0743(8) .031(5) 1.00000 Uani C8b .0336(7) .2679(12) .1820(8) .030(5) 1.00000 Uani C9b .0031(8) .3380(12) .2637(8) .042(6) 1.00000 Uani C10b -.1213(9) .3431(13) .2538(9) .049(6) 1.00000 Uani C11b -.2113(8) .2806(13) .1692(9) .049(6) 1.00000 Uani C12b -.1829(7) .2132(12) .0873(8) .041(6) 1.00000 Uani C13b -.0582(7) .2093(11) .0962(7) .031(5) 1.00000 Uani C14b -.0596(8) .0861(13) -.0736(9) .051(6) 1.00000 Uani C15b .3620(9) .0188(13) .1846(10) .048(6) 1.00000 Uani H02a .273(8) .359(9) .239(8) .04000 1.00000 Uiso H1a .45403 .52822 .46078 .04000 1.00000 Uiso H2a .47882 .67706 .28363 .04000 1.00000 Uiso H31a .60194 .42269 .37892 .04000 1.00000 Uiso H32a .62281 .49724 .27709 .04000 1.00000 Uiso H41a .78521 .54761 .43764 .04000 1.00000 Uiso H42a .71701 .68749 .38113 .04000 1.00000 Uiso H51a .68227 .55530 .56293 .04000 1.00000 Uiso H52a .74622 .70485 .56320 .04000 1.00000 Uiso H61a .53831 .73129 .56368 .04000 1.00000 Uiso H62a .55614 .80243 .45943 .04000 1.00000 Uiso H9a .07795 .95176 .22384 .04000 1.00000 Uiso H10a -.09008 .98963 .28627 .04000 1.00000 Uiso H11a -.10959 .86386 .43440 .04000 1.00000 Uiso H12a .04671 .70626 .53154 .04000 1.00000 Uiso H141a .24523 .60402 .61399 .04000 1.00000 Uiso H142a .28166 .47738 .55014 .04000 1.00000 Uiso H143a .38213 .59090 .60956 .04000 1.00000 Uiso H02b .295(8) -.140(10) .208(8) .04000 1.00000 Uiso H1b .19440 .05656 -.01609 .04000 1.00000 Uiso H2b .36891 .21911 .13613 .04000 1.00000 Uiso H31b .52110 .08540 .08763 .04000 1.00000 Uiso H32b .41260 .00593 -.00202 .04000 1.00000 Uiso H41b .46608 .29690 -.00436 .04000 1.00000 Uiso H42b .49228 .18230 -.08335 .04000 1.00000 Uiso H51b .30909 .31141 -.16968 .04000 1.00000 Uiso H52b .28059 .14730 -.16563 .04000 1.00000 Uiso H61b .23879 .35434 -.02394 .04000 1.00000 Uiso H62b .13265 .27249 -.11411 .04000 1.00000 Uiso H9b .06588 .38199 .32432 .04000 1.00000 Uiso H10b -.14602 .39031 .31000 .04000 1.00000 Uiso H11b -.29760 .28516 .16680 .04000 1.00000 Uiso H12b -.24657 .16958 .02672 .04000 1.00000 Uiso H141b -.12003 .01765 -.06473 .04000 1.00000 Uiso H142b -.10188 .15586 -.12705 .04000 1.00000 Uiso H143b .00191 .03654 -.09805 .04000 1.00000 Uiso 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 O1a .052(4) .056(5) .025(5) -.013(4) .012(3) -.005(4) O2a .040(4) .038(4) .028(5) -.017(3) .008(3) -.004(3) N1a .037(4) .035(5) .036(6) .009(4) .015(4) .006(4) N2a .028(4) .031(5) .029(5) .000(4) .010(4) .003(4) C1a .030(5) .023(5) .028(6) -.003(4) .007(4) .001(4) C2a .026(5) .024(5) .030(6) -.001(4) .011(4) -.001(4) C3a .029(5) .043(6) .042(7) .000(5) .016(5) -.008(5) C4a .028(5) .054(7) .056(8) -.001(5) .009(5) -.011(6) C5a .034(5) .052(7) .042(7) -.008(5) .003(5) -.015(5) C6a .037(5) .034(6) .034(7) -.005(4) .008(5) -.009(5) C7a .035(5) .022(5) .024(6) -.002(4) .010(4) .001(4) C8a .032(5) .033(5) .033(7) .005(4) .008(5) -.003(5) C9a .042(6) .040(6) .042(8) .011(5) .008(5) .005(5) C10a .030(5) .046(6) .062(9) .015(5) .007(5) -.008(6) C11a .026(5) .060(7) .068(9) .005(5) .019(5) -.001(7) C12a .039(6) .053(7) .050(8) -.002(6) .021(5) .000(6) C13a .028(5) .033(6) .032(7) -.002(4) .009(4) -.001(5) C14a .045(6) .069(7) .050(8) .011(5) .028(5) .019(6) C15a .026(5) .029(5) .033(7) .002(4) .009(5) -.000(5) O1b .068(6) .124(8) .069(7) -.022(6) -.017(5) .035(6) O2b .066(5) .043(5) .047(6) -.002(4) .020(4) .007(4) N1b .027(4) .030(5) .032(6) -.004(3) .007(4) -.002(4) N2b .029(4) .039(5) .027(5) -.005(4) .007(4) -.009(4) C1b .037(5) .029(5) .030(6) -.001(4) .014(4) -.009(5) C2b .036(5) .029(5) .036(6) .001(4) .016(5) .001(5) C3b .037(5) .041(6) .055(8) .001(5) .019(5) -.007(5) C4b .059(6) .054(7) .060(8) -.002(5) .040(6) -.002(6) C5b .062(7) .059(7) .044(8) .001(6) .029(6) .004(6) C6b .043(5) .053(7) .035(7) .007(5) .013(5) .005(6) C7b .033(5) .028(5) .030(7) -.002(4) .008(4) -.001(5) C8b .028(5) .032(5) .030(7) .003(4) .008(5) .006(5) C9b .046(6) .048(6) .030(7) .007(5) .011(5) -.005(5) C10b .050(6) .059(7) .047(8) .019(6) .028(6) .002(6) C11b .038(6) .062(7) .051(8) .009(5) .022(6) .006(6) C12b .029(5) .049(6) .045(7) .002(5) .010(5) -.003(5) C13b .029(5) .030(5) .032(7) -.002(4) .007(5) .000(5) C14b .039(5) .062(7) .048(8) -.015(5) .009(5) -.022(6) C15b .034(6) .055(7) .057(9) -.009(6) .017(6) -.008(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance O1a C15a . . 1.210(13) O2a C15a . . 1.318(14) O2a H02a . . .89(9) N1a C7a . . 1.326(12) N1a C8a . . 1.395(12) N2a C7a . . 1.363(13) N2a C13a . . 1.383(11) N2a C14a . . 1.455(14) C1a C2a . . 1.531(14) C1a C6a . . 1.525(12) C1a C7a . . 1.484(12) C2a C3a . . 1.535(12) C2a C15a . . 1.522(12) C3a C4a . . 1.510(13) C4a C5a . . 1.516(17) C5a C6a . . 1.538(13) C8a C9a . . 1.393(13) C8a C13a . . 1.393(15) C9a C10a . . 1.370(16) C10a C11a . . 1.395(18) C11a C12a . . 1.374(14) C12a C13a . . 1.385(14) O1b C15b . . 1.207(13) O2b C15b . . 1.297(14) O2b H02b . . .86(10) N1b C7b . . 1.323(13) N1b C8b . . 1.397(12) N2b C7b . . 1.363(10) N2b C13b . . 1.383(13) N2b C14b . . 1.458(13) C1b C2b . . 1.528(10) C1b C6b . . 1.538(15) C1b C7b . . 1.501(14) C2b C3b . . 1.538(15) C2b C15b . . 1.522(16) C3b C4b . . 1.516(17) C4b C5b . . 1.510(13) C5b C6b . . 1.524(16) C8b C9b . . 1.402(15) C8b C13b . . 1.388(11) C9b C10b . . 1.389(14) C10b C11b . . 1.384(14) C11b C12b . . 1.379(17) C12b C13b . . 1.394(12) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle C15a O2a H02a . . . 108(7) C7a N1a C8a . . . 106.0(8) C7a N2a C13a . . . 107.9(8) C7a N2a C14a . . . 126.9(8) C13a N2a C14a . . . 125.1(9) C2a C1a C6a . . . 109.7(8) C2a C1a C7a . . . 112.7(7) C6a C1a C7a . . . 111.0(8) C1a C2a C3a . . . 109.9(7) C1a C2a C15a . . . 113.7(8) C3a C2a C15a . . . 109.0(8) C2a C3a C4a . . . 111.3(9) C3a C4a C5a . . . 112.4(9) C4a C5a C6a . . . 110.8(8) C1a C6a C5a . . . 110.9(9) N1a C7a N2a . . . 111.4(8) N1a C7a C1a . . . 125.3(9) N2a C7a C1a . . . 123.2(8) N1a C8a C9a . . . 130.7(10) N1a C8a C13a . . . 109.2(8) C9a C8a C13a . . . 120.1(9) C8a C9a C10a . . . 118.1(10) C9a C10a C11a . . . 121.1(10) C10a C11a C12a . . . 121.7(10) C11a C12a C13a . . . 116.9(11) N2a C13a C8a . . . 105.5(8) N2a C13a C12a . . . 132.5(10) C8a C13a C12a . . . 122.0(8) O1a C15a O2a . . . 124.3(8) O1a C15a C2a . . . 122.7(9) O2a C15a C2a . . . 113.0(9) C15b O2b H02b . . . 108(6) C7b N1b C8b . . . 105.5(7) C7b N2b C13b . . . 107.4(8) C7b N2b C14b . . . 127.9(9) C13b N2b C14b . . . 124.7(7) C2b C1b C6b . . . 109.9(8) C2b C1b C7b . . . 112.9(8) C6b C1b C7b . . . 109.4(8) C1b C2b C3b . . . 110.1(8) C1b C2b C15b . . . 115.7(8) C3b C2b C15b . . . 108.5(9) C2b C3b C4b . . . 110.6(9) C3b C4b C5b . . . 111.3(9) C4b C5b C6b . . . 111.0(9) C1b C6b C5b . . . 111.4(9) N1b C7b N2b . . . 112.0(9) N1b C7b C1b . . . 125.6(7) N2b C7b C1b . . . 122.3(8) N1b C8b C9b . . . 130.1(8) N1b C8b C13b . . . 109.5(9) C9b C8b C13b . . . 120.3(8) C8b C9b C10b . . . 116.5(9) C9b C10b C11b . . . 122.3(11) C10b C11b C12b . . . 121.8(10) C11b C12b C13b . . . 116.1(8) N2b C13b C8b . . . 105.6(8) N2b C13b C12b . . . 131.4(8) C8b C13b C12b . . . 122.9(10) O1b C15b O2b . . . 123.5(12) O1b C15b C2b . . . 123.0(11) O2b C15b C2b . . . 113.5(9) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion H02a O2a C15a O1a . . . . 2(6) H02a O2a C15a C2a . . . . -176(6) C8a N1a C7a N2a . . . . .5(11) C8a N1a C7a C1a . . . . -176.7(9) C7a N1a C8a C9a . . . . 177.4(10) C7a N1a C8a C13a . . . . -1.4(11) C13a N2a C7a N1a . . . . .5(11) C13a N2a C7a C1a . . . . 177.8(9) C14a N2a C7a N1a . . . . -177.8(9) C14a N2a C7a C1a . . . . -.6(15) C7a N2a C13a C8a . . . . -1.4(10) C7a N2a C13a C12a . . . . 178.9(11) C14a N2a C13a C8a . . . . 177.0(9) C14a N2a C13a C12a . . . . -2.7(17) C6a C1a C2a C3a . . . . 58.9(10) C6a C1a C2a C15a . . . . -178.6(8) C7a C1a C2a C3a . . . . -176.8(8) C7a C1a C2a C15a . . . . -54.3(11) C2a C1a C6a C5a . . . . -58.8(10) C7a C1a C6a C5a . . . . 176.1(9) C2a C1a C7a N1a . . . . -34.3(13) C2a C1a C7a N2a . . . . 148.8(9) C6a C1a C7a N1a . . . . 89.2(11) C6a C1a C7a N2a . . . . -87.7(11) C1a C2a C3a C4a . . . . -56.9(11) C15a C2a C3a C4a . . . . 177.8(9) C1a C2a C15a O1a . . . . 153.8(9) C1a C2a C15a O2a . . . . -28.5(11) C3a C2a C15a O1a . . . . -83.3(11) C3a C2a C15a O2a . . . . 94.5(10) C2a C3a C4a C5a . . . . 54.7(12) C3a C4a C5a C6a . . . . -53.6(12) C4a C5a C6a C1a . . . . 55.7(12) N1a C8a C9a C10a . . . . -179.1(10) C13a C8a C9a C10a . . . . -.5(15) N1a C8a C13a N2a . . . . 1.7(11) N1a C8a C13a C12a . . . . -178.6(9) C9a C8a C13a N2a . . . . -177.2(9) C9a C8a C13a C12a . . . . 2.5(15) C8a C9a C10a C11a . . . . -1.2(16) C9a C10a C11a C12a . . . . 1.0(17) C10a C11a C12a C13a . . . . 1.0(16) C11a C12a C13a N2a . . . . 177.0(10) C11a C12a C13a C8a . . . . -2.7(15) H02b O2b C15b O1b . . . . 2(8) H02b O2b C15b C2b . . . . -179(8) C8b N1b C7b N2b . . . . .0(12) C8b N1b C7b C1b . . . . 175.7(10) C7b N1b C8b C9b . . . . -176.6(11) C7b N1b C8b C13b . . . . -.2(12) C13b N2b C7b N1b . . . . .1(12) C13b N2b C7b C1b . . . . -175.7(9) C14b N2b C7b N1b . . . . 178.5(10) C14b N2b C7b C1b . . . . 2.6(16) C7b N2b C13b C8b . . . . -.3(11) C7b N2b C13b C12b . . . . 178.3(11) C14b N2b C13b C8b . . . . -178.6(10) C14b N2b C13b C12b . . . . -.1(18) C6b C1b C2b C3b . . . . -57.2(11) C6b C1b C2b C15b . . . . 179.4(9) C7b C1b C2b C3b . . . . -179.6(9) C7b C1b C2b C15b . . . . 56.9(12) C2b C1b C6b C5b . . . . 56.5(11) C7b C1b C6b C5b . . . . -179.0(7) C2b C1b C7b N1b . . . . 28.8(14) C2b C1b C7b N2b . . . . -156.0(9) C6b C1b C7b N1b . . . . -93.9(11) C6b C1b C7b N2b . . . . 81.3(11) C1b C2b C3b C4b . . . . 58.0(11) C15b C2b C3b C4b . . . . -174.5(8) C1b C2b C15b O1b . . . . -152.6(12) C1b C2b C15b O2b . . . . 28.5(14) C3b C2b C15b O1b . . . . 83.1(14) C3b C2b C15b O2b . . . . -95.7(11) C2b C3b C4b C5b . . . . -57.3(12) C3b C4b C5b C6b . . . . 56.1(13) C4b C5b C6b C1b . . . . -55.8(11) N1b C8b C9b C10b . . . . 176.8(11) C13b C8b C9b C10b . . . . .7(16) N1b C8b C13b N2b . . . . .3(12) N1b C8b C13b C12b . . . . -178.4(10) C9b C8b C13b N2b . . . . 177.1(10) C9b C8b C13b C12b . . . . -1.6(16) C8b C9b C10b C11b . . . . 1.2(17) C9b C10b C11b C12b . . . . -2.3(19) C10b C11b C12b C13b . . . . 1.4(17) C11b C12b C13b N2b . . . . -177.8(11) C11b C12b C13b C8b . . . . .5(16) 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_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O2a H02a N1b . . . 0.89(8) 1.77(8) 2.638(9) 164(10) O2b H02b N1a . . 1_545 0.86(10) 1.86(10) 2.679(12) 160(9) #=END=============================================================== # Attachment 'verdan-6.cif' data_verdan-6 _database_code_depnum_ccdc_archive 'CCDC 683803' #--- S-6 ------------------------------------------------------------ _audit_creation_date 2006-11-20 _audit_creation_method from_xtal_archive_file_using_CIFIO _audit_update_record 2007-09-19 _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.0.1 _chemical_formula_moiety 'C10 H10 N2 O3' _chemical_formula_sum 'C10 H10 N2 O3' _chemical_formula_weight 206.2 _chemical_absolute_configuration syn _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'p 2yb' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,1/2+y,-z _cell_length_a 4.6354(5) _cell_length_b 10.4827(15) _cell_length_c 10.2152(12) _cell_angle_alpha 90.00000 _cell_angle_beta 101.112(13) _cell_angle_gamma 90.00000 _cell_volume 487.07(11) _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_meas not_measured _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _cell_measurement_reflns_used 4892 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.9 _cell_measurement_temperature 220 _exptl_absorpt_coefficient_mu .106 _exptl_crystal_F_000 216 _exptl_crystal_description plate _exptl_crystal_size_max .41 _exptl_crystal_size_mid .184 _exptl_crystal_size_min .034 _exptl_crystal_colour colorless _diffrn_measurement_device_type 'Stoe Ipds' _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 6 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'XRED; Stoe & Cie, 1999' _exptl_absorpt_correction_T_min .9700 _exptl_absorpt_correction_T_max .9964 _diffrn_reflns_number 7468 _reflns_number_total 2275 _reflns_number_gt 1575 _reflns_threshold_expression 'refl observed if Fo > 3.99 \s(Fo)' _diffrn_reflns_theta_max 27.9 _diffrn_reflns_theta_full 27.9 _diffrn_measured_fraction_theta_max 1.0 _diffrn_measured_fraction_theta_full 1.0 _reflns_Friedel_coverage .95 _diffrn_reflns_av_R_equivalents .047 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_standards_number ? _diffrn_standards_decay_% 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .031 _refine_ls_wR_factor_ref .031 _refine_ls_goodness_of_fit_ref 1.66(4) _refine_ls_number_reflns 1574 _refine_ls_number_parameters 138 _refine_ls_weighting_scheme calc _refine_ls_weighting_details \w=1/[\s^2^(Fo)+0.0002(Fo^2^)] _refine_ls_hydrogen_treatment mixed _refine_ls_shift/su_max .0003 _refine_diff_density_max .461 _refine_diff_density_min -.554 _refine_ls_extinction_method none _refine_ls_abs_structure_details Flack_xabs_not_refined _refine_ls_abs_structure_Flack 0 _refine_special_details ; Hydrogen treatment: - Hydrogen atom of -OH group was observed and refined with restraints on bond lengths and bond angles. - Coordinates of other H atoms were calculated. Definition of polar origin: y(O1) = fixed as a hard constraint Flack parameter was fixed to 0. ; _computing_data_collection 'EXPOSE (Stoe & Cie, 1999)' _computing_cell_refinement 'CELL (Stoe & Cie, 1999)' _computing_data_reduction 'XRED (Stoe & Cie, 1999)' _computing_structure_solution SIR97 _computing_structure_refinement xtal_CRYLSQ _computing_molecular_graphics xtal_gx3 _computing_publication_material xtal_CIFIO loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 .4889(6) .30000 .5818(3) .0315(16) 1.00000 Uani O2 .4319(7) .6528(5) .7123(3) .0359(16) 1.00000 Uani O3 .4492(6) .5705(4) .5137(3) .0308(15) 1.00000 Uani N1 .1582(8) .3265(4) .3164(4) .0289(18) 1.00000 Uani N2 -.1589(7) .4526(5) .3827(4) .0282(18) 1.00000 Uani C1 -.0121(10) .3801(5) .2020(4) .031(3) 1.00000 Uani C2 -.0058(11) .3648(6) .0672(5) .042(3) 1.00000 Uani C3 -.1984(11) .4389(7) -.0213(5) .049(3) 1.00000 Uani C4 -.3883(11) .5273(6) .0219(5) .046(3) 1.00000 Uani C5 -.4008(10) .5395(5) .1559(5) .038(3) 1.00000 Uani C6 -.2102(9) .4626(5) .2445(4) .029(3) 1.00000 Uani C7 .0654(9) .3721(5) .4227(4) .025(2) 1.00000 Uani C8 .1947(9) .3400(5) .5666(4) .026(2) 1.00000 Uani C9 .1885(8) .4556(5) .6579(4) .027(2) 1.00000 Uani C10 .3744(9) .5678(5) .6269(4) .0244(19) 1.00000 Uani H101 .497(3) .233(4) .539(5) .05000 1.00000 Uiso H01 .30435 .27113 .31800 .05000 1.00000 Uiso H02 -.25907 .49315 .43619 .05000 1.00000 Uiso H2 .12176 .30749 .03819 .05000 1.00000 Uiso H3 -.20267 .42993 -.11227 .05000 1.00000 Uiso H4 -.50761 .57850 -.04055 .05000 1.00000 Uiso H5 -.52959 .59604 .18508 .05000 1.00000 Uiso H8 .07341 .27083 .59148 .05000 1.00000 Uiso H91 -.01563 .48441 .64839 .05000 1.00000 Uiso H92 .26189 .42876 .75018 .05000 1.00000 Uiso 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 .0278(19) .0287(16) .0363(17) .0025(12) .0019(12) -.0053(13) O2 .0474(19) .0318(15) .0301(15) -.0124(14) .0111(12) -.0081(14) O3 .0377(19) .0262(14) .0320(16) -.0023(14) .0155(12) -.0011(13) N1 .026(3) .0341(19) .0273(18) .0015(15) .0064(14) -.0030(15) N2 .0251(19) .0333(19) .0267(19) .0016(17) .0060(13) -.0018(15) C1 .026(3) .039(3) .027(3) -.0033(18) .0053(16) .0007(19) C2 .037(3) .061(3) .028(3) -.001(3) .0091(18) -.005(3) C3 .041(3) .083(4) .021(3) -.007(3) .0054(18) .006(3) C4 .036(3) .064(4) .035(3) -.001(3) -.000(2) .015(3) C5 .028(3) .047(3) .036(3) .002(2) .0032(18) .007(2) C6 .024(3) .038(3) .025(3) -.0047(19) .0045(15) .0003(19) C7 .022(3) .0255(18) .030(2) -.0027(17) .0064(15) -.0018(18) C8 .025(3) .025(2) .027(3) -.0031(17) .0038(15) .0031(16) C9 .027(3) .029(3) .025(3) -.0009(19) .0066(15) -.0041(18) C10 .023(3) .0234(19) .027(2) .0053(17) .0057(15) .0006(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance O1 C8 . . 1.407(5) O1 H101 . . .83(4) O2 C10 . . 1.240(6) O3 C10 . . 1.271(5) N1 C1 . . 1.396(5) N1 C7 . . 1.331(6) N2 C6 . . 1.390(5) N2 C7 . . 1.340(6) C1 C2 . . 1.392(6) C1 C6 . . 1.390(7) C2 C3 . . 1.380(7) C3 C4 . . 1.407(9) C4 C5 . . 1.387(7) C5 C6 . . 1.393(6) C7 C8 . . 1.514(5) C8 C9 . . 1.533(7) C9 C10 . . 1.527(7) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle C8 O1 H101 . . . 109.5(8) C1 N1 C7 . . . 108.6(4) C6 N2 C7 . . . 109.1(4) N1 C1 C2 . . . 131.7(5) N1 C1 C6 . . . 106.8(4) C2 C1 C6 . . . 121.5(4) C1 C2 C3 . . . 116.6(5) C2 C3 C4 . . . 122.0(5) C3 C4 C5 . . . 121.2(5) C4 C5 C6 . . . 116.4(5) N2 C6 C1 . . . 106.1(4) N2 C6 C5 . . . 131.8(5) C1 C6 C5 . . . 122.1(4) N1 C7 N2 . . . 109.3(4) N1 C7 C8 . . . 125.6(4) N2 C7 C8 . . . 125.1(4) O1 C8 C7 . . . 111.6(4) O1 C8 C9 . . . 107.4(3) C7 C8 C9 . . . 111.3(4) C8 C9 C10 . . . 113.9(4) O2 C10 O3 . . . 124.4(5) O2 C10 C9 . . . 117.5(4) O3 C10 C9 . . . 118.0(4) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion H101 O1 C8 C7 . . . . -63(4) H101 O1 C8 C9 . . . . 175(4) C7 N1 C1 C2 . . . . 179.9(6) C7 N1 C1 C6 . . . . 1.0(6) C1 N1 C7 N2 . . . . .3(6) C1 N1 C7 C8 . . . . -178.9(5) C7 N2 C6 C1 . . . . 2.2(5) C7 N2 C6 C5 . . . . -174.6(5) C6 N2 C7 N1 . . . . -1.6(6) C6 N2 C7 C8 . . . . 177.7(4) N1 C1 C2 C3 . . . . -176.5(6) C6 C1 C2 C3 . . . . 2.3(8) N1 C1 C6 N2 . . . . -1.9(5) N1 C1 C6 C5 . . . . 175.3(5) C2 C1 C6 N2 . . . . 179.1(5) C2 C1 C6 C5 . . . . -3.8(8) C1 C2 C3 C4 . . . . 1.1(9) C2 C3 C4 C5 . . . . -3.3(9) C3 C4 C5 C6 . . . . 1.8(8) C4 C5 C6 N2 . . . . 178.0(5) C4 C5 C6 C1 . . . . 1.6(7) N1 C7 C8 O1 . . . . 24.3(6) N1 C7 C8 C9 . . . . 144.3(5) N2 C7 C8 O1 . . . . -154.8(4) N2 C7 C8 C9 . . . . -34.8(6) O1 C8 C9 C10 . . . . 59.4(4) C7 C8 C9 C10 . . . . -63.0(5) C8 C9 C10 O2 . . . . -164.9(4) C8 C9 C10 O3 . . . . 18.1(5) 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_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O1 H101 O3 . . 2_646 0.83(4) 1.82(4) 2.633(4) 165(4) N1 H01 O2 . . 2_646 0.89 1.81 2.688(5) 169 N2 H02 O3 . . 1_455 0.89 1.88 2.748(5) 166 #=END============================================================ # Attachment 'verdan-7.cif' data_verdan-7 _database_code_depnum_ccdc_archive 'CCDC 683804' #--- 2R,3S-7.2H2O --------------------------------------------------- _audit_creation_date 2006-02-13 _audit_creation_method from_xtal_archive_file_using_CIFIO _audit_update_record 2007-09-19 _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.0.1 _chemical_formula_moiety 'C10 H10 N2 O4, 2(H2 O)' _chemical_formula_sum 'C10 H14 N2 O6' _chemical_formula_weight 258.3 _chemical_absolute_configuration syn _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z _cell_length_a 6.8790(3) _cell_length_b 10.3028(7) _cell_length_c 15.9544(8) _cell_angle_alpha 90.00000 _cell_angle_beta 90.00000 _cell_angle_gamma 90.00000 _cell_volume 1130.74(11) _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_meas not_measured _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 4.4 _cell_measurement_theta_max 29.1 _cell_measurement_temperature 200 _exptl_absorpt_coefficient_mu .127 _exptl_crystal_description prism _exptl_crystal_size_max .35 _exptl_crystal_size_mid .12 _exptl_crystal_size_min .063 _exptl_crystal_colour colourless _diffrn_measurement_device_type 'Stoe Ipds' _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 6 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'XRED; Stoe & Cie, 1999' _exptl_absorpt_correction_T_min .9669 _exptl_absorpt_correction_T_max .9922 _exptl_crystal_F_000 544 _diffrn_reflns_number 17918 _reflns_Friedel_coverage .86 _reflns_number_total 3041 _reflns_number_gt 2140 _diffrn_measured_fraction_theta_max 1.0 _diffrn_measured_fraction_theta_full 1.0 _reflns_threshold_expression 'refl observed if Fo > 3.99 \s(Fo)' _diffrn_reflns_theta_max 29.1 _diffrn_reflns_theta_full 29.1 _diffrn_reflns_av_R_equivalents .053 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_standards_decay_% 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .032 _refine_ls_wR_factor_ref .032 _refine_ls_goodness_of_fit_ref 1.62(4) _refine_ls_number_reflns 2178 _refine_ls_number_parameters 219 _refine_ls_weighting_scheme calc _refine_ls_weighting_details \w=1/[\s^2^(Fo)+0.0003(Fo^2^)] _refine_ls_hydrogen_treatment refall _refine_ls_shift/su_max .0017 _refine_diff_density_max .41 _refine_diff_density_min -.434 _refine_ls_extinction_method none _refine_ls_extinction_coef .00000 _refine_ls_abs_structure_details Flack_xabs_not_refined _refine_ls_abs_structure_Flack 0 _publ_section_exptl_refinement ; Hydrogen atom have been observed and refined. Restraints on bond lengths and bond angles have been applied to -OH groups and water molecules. The Flack parameter was fixed to 0.0 ; _computing_data_collection 'EXPOSE (Stoe & Cie, 1999)' _computing_cell_refinement 'CELL (Stoe & Cie, 1999)' _computing_data_reduction 'XRED (Stoe & Cie, 1999)' _computing_structure_solution SIR97 _computing_structure_refinement xtal_CRYLSQ _computing_molecular_graphics xtal_gx3 _computing_publication_material xtal_CIFIO loop_ _atom_type_symbol _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .002 .002 H Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 0 0 N Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .004 .003 O Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .008 .006 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 .6005(4) 1.2284(3) .51346(16) .0264(13) 1.00000 Uani O2 .8878(4) 1.1741(3) .61885(14) .0221(11) 1.00000 Uani O3 .4818(4) 1.3152(3) .72940(15) .0243(12) 1.00000 Uani O4 .7801(4) 1.3905(3) .70488(18) .0351(13) 1.00000 Uani N1 .5814(4) .9677(3) .47851(18) .0193(13) 1.00000 Uani N2 .5579(4) .9031(3) .60773(17) .0192(13) 1.00000 Uani C1 .5784(5) .8326(3) .4758(3) .0200(14) 1.00000 Uani C2 .5836(6) .7455(4) .4087(3) .0275(18) 1.00000 Uani C3 .5781(6) .6159(4) .4288(3) .0310(18) 1.00000 Uani C4 .5669(6) .5727(4) .5123(3) .0310(19) 1.00000 Uani C5 .5595(6) .6588(3) .5785(3) .0268(18) 1.00000 Uani C6 .5649(5) .7909(3) .5586(3) .0209(15) 1.00000 Uani C7 .5685(5) 1.0061(3) .55704(19) .0171(14) 1.00000 Uani C8 .5562(5) 1.1482(3) .58304(19) .0170(14) 1.00000 Uani C9 .6996(5) 1.1772(3) .6537(2) .0170(14) 1.00000 Uani C10 .6527(5) 1.3075(3) .69830(19) .0182(14) 1.00000 Uani O1w .1780(4) 1.1346(3) .72746(18) .0365(14) 1.00000 Uani O2w .8422(4) .9522(3) .82119(17) .0317(13) 1.00000 Uani H001 .599(6) 1.017(3) .4320(18) .021(9) 1.00000 Uiso H002 .535(6) .901(4) .6638(13) .037(11) 1.00000 Uiso H2 .588(6) .778(4) .354(3) .036(11) 1.00000 Uiso H3 .589(7) .554(4) .385(3) .038(11) 1.00000 Uiso H4 .563(6) .480(4) .524(3) .033(11) 1.00000 Uiso H5 .552(6) .630(5) .635(3) .035(11) 1.00000 Uiso H8 .420(6) 1.162(4) .604(3) .027(10) 1.00000 Uiso H9 .679(5) 1.113(4) .696(2) .016(8) 1.00000 Uiso H01 .730(4) 1.232(8) .506(4) .17(5) 1.00000 Uiso H02 .976(4) 1.167(4) .6590(15) .030(11) 1.00000 Uiso H11w .275(5) 1.193(3) .737(3) .047(13) 1.00000 Uiso H12w .209(6) 1.058(3) .751(3) .051(14) 1.00000 Uiso H21w .949(4) .906(4) .807(3) .034(11) 1.00000 Uiso H22w .736(4) .907(4) .807(3) .054(14) 1.00000 Uiso 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 .0374(15) .0176(11) .0242(13) -.0021(10) -.0065(12) .0041(10) O2 .0182(11) .0277(11) .0204(11) .0032(9) -.0002(10) -.0025(10) O3 .0226(11) .0270(11) .0232(12) .0032(10) .0007(10) -.0063(11) O4 .0291(12) .0220(11) .0541(17) -.0053(11) .0021(12) -.0138(12) N1 .0231(14) .0160(11) .0188(13) -.0022(12) .0027(13) -.0018(12) N2 .0234(13) .0133(11) .0208(14) -.0024(11) .0001(12) -.0002(11) C1 .0186(14) .0168(13) .0246(16) -.0020(13) .0029(15) -.0036(13) C2 .0267(18) .0292(18) .0266(19) -.0037(15) .0022(16) -.0102(15) C3 .0270(17) .0247(16) .041(3) -.0019(15) .0048(17) -.0195(17) C4 .0271(17) .0148(15) .051(3) -.0005(14) -.0041(18) -.0051(15) C5 .0266(17) .0200(15) .034(2) -.0031(14) -.0050(17) .0027(15) C6 .0193(15) .0185(14) .0247(16) -.0024(13) -.0014(14) -.0026(13) C7 .0151(15) .0177(13) .0186(15) -.0014(12) -.0007(13) -.0007(13) C8 .0206(16) .0130(13) .0173(14) .0002(12) -.0023(14) -.0020(11) C9 .0184(14) .0149(12) .0177(15) .0008(12) -.0001(13) -.0004(13) C10 .0222(14) .0161(13) .0164(15) .0023(12) -.0044(13) -.0012(12) O1w .0333(14) .0310(13) .0452(16) -.0099(12) -.0149(13) .0155(13) O2w .0290(13) .0337(13) .0324(14) -.0046(12) .0005(12) -.0100(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance O1 C8 . . 1.417(4) O1 H01 . . .90(3) O2 C9 . . 1.409(4) O2 H02 . . .88(3) O3 C10 . . 1.278(4) O4 C10 . . 1.229(4) N1 C1 . . 1.392(4) N1 C7 . . 1.317(5) N1 H001 . . .91(3) N2 C6 . . 1.398(4) N2 C7 . . 1.336(4) N2 H002 . . .91(3) C1 C2 . . 1.397(5) C1 C6 . . 1.392(5) C2 C3 . . 1.374(5) C2 H2 . . .93(5) C3 C4 . . 1.408(6) C3 H3 . . .94(5) C4 C5 . . 1.380(6) C4 H4 . . .97(4) C5 C6 . . 1.397(5) C5 H5 . . .96(5) C7 C8 . . 1.524(4) C8 C9 . . 1.528(5) C8 H8 . . 1.01(4) C9 C10 . . 1.553(5) C9 H9 . . .96(4) O1w H11w . . .91(4) O1w H12w . . .90(3) O2w H21w . . .90(3) O2w H22w . . .90(3) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle C8 O1 H01 . . . 110(5) C9 O2 H02 . . . 110.2(15) C1 N1 C7 . . . 109.2(3) C1 N1 H001 . . . 122.3(19) C7 N1 H001 . . . 128.3(19) C6 N2 C7 . . . 108.4(3) C6 N2 H002 . . . 123(3) C7 N2 H002 . . . 128(3) N1 C1 C2 . . . 131.7(4) N1 C1 C6 . . . 106.3(3) C2 C1 C6 . . . 122.0(3) C1 C2 C3 . . . 116.5(4) C1 C2 H2 . . . 119(3) C3 C2 H2 . . . 124(3) C2 C3 C4 . . . 121.9(4) C2 C3 H3 . . . 119(3) C4 C3 H3 . . . 119(3) C3 C4 C5 . . . 121.5(4) C3 C4 H4 . . . 119(3) C5 C4 H4 . . . 119(3) C4 C5 C6 . . . 116.8(4) C4 C5 H5 . . . 122(3) C6 C5 H5 . . . 122(3) N2 C6 C1 . . . 106.2(3) N2 C6 C5 . . . 132.6(4) C1 C6 C5 . . . 121.2(3) N1 C7 N2 . . . 109.9(3) N1 C7 C8 . . . 123.4(3) N2 C7 C8 . . . 126.5(3) O1 C8 C7 . . . 109.6(3) O1 C8 C9 . . . 109.0(3) O1 C8 H8 . . . 112(3) C7 C8 C9 . . . 110.7(3) C7 C8 H8 . . . 106(2) C9 C8 H8 . . . 109(3) O2 C9 C8 . . . 107.3(3) O2 C9 C10 . . . 113.1(3) O2 C9 H9 . . . 113.3(19) C8 C9 C10 . . . 111.9(3) C8 C9 H9 . . . 106.8(19) C10 C9 H9 . . . 104(2) O3 C10 O4 . . . 125.4(3) O3 C10 C9 . . . 115.0(3) O4 C10 C9 . . . 119.5(3) H11w O1w H12w . . . 109(4) H21w O2w H22w . . . 109(3) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion H01 O1 C8 C7 . . . . -79(5) H01 O1 C8 C9 . . . . 42(5) H01 O1 C8 H8 . . . . 163(6) H02 O2 C9 C8 . . . . -163(3) H02 O2 C9 C10 . . . . 73(3) H02 O2 C9 H9 . . . . -46(4) C7 N1 C1 C2 . . . . 178.3(4) C7 N1 C1 C6 . . . . -.6(4) H001 N1 C1 C2 . . . . -6(3) H001 N1 C1 C6 . . . . 175(3) C1 N1 C7 N2 . . . . .3(4) C1 N1 C7 C8 . . . . -176.5(3) H001 N1 C7 N2 . . . . -175(4) H001 N1 C7 C8 . . . . 8(4) C7 N2 C6 C1 . . . . -.6(4) C7 N2 C6 C5 . . . . 179.9(4) H002 N2 C6 C1 . . . . 173(3) H002 N2 C6 C5 . . . . -6(3) C6 N2 C7 N1 . . . . .2(4) C6 N2 C7 C8 . . . . 176.8(4) H002 N2 C7 N1 . . . . -173(4) H002 N2 C7 C8 . . . . 4(4) N1 C1 C2 C3 . . . . -179.9(4) N1 C1 C2 H2 . . . . -1(3) C6 C1 C2 C3 . . . . -1.1(5) C6 C1 C2 H2 . . . . 178(3) N1 C1 C6 N2 . . . . .7(4) N1 C1 C6 C5 . . . . -179.7(4) C2 C1 C6 N2 . . . . -178.4(3) C2 C1 C6 C5 . . . . 1.2(6) C1 C2 C3 C4 . . . . .3(6) C1 C2 C3 H3 . . . . -176(3) H2 C2 C3 C4 . . . . -178(4) H2 C2 C3 H3 . . . . 5(5) C2 C3 C4 C5 . . . . .5(6) C2 C3 C4 H4 . . . . 180(3) H3 C3 C4 C5 . . . . 177(3) H3 C3 C4 H4 . . . . -3(5) C3 C4 C5 C6 . . . . -.4(6) C3 C4 C5 H5 . . . . -180(3) H4 C4 C5 C6 . . . . -180(3) H4 C4 C5 H5 . . . . 0(4) C4 C5 C6 N2 . . . . 179.0(4) C4 C5 C6 C1 . . . . -.4(6) H5 C5 C6 N2 . . . . -1(3) H5 C5 C6 C1 . . . . 179(3) N1 C7 C8 O1 . . . . -11.9(5) N1 C7 C8 C9 . . . . -132.1(4) N1 C7 C8 H8 . . . . 110(3) N2 C7 C8 O1 . . . . 171.9(4) N2 C7 C8 C9 . . . . 51.7(5) N2 C7 C8 H8 . . . . -67(3) O1 C8 C9 O2 . . . . -49.2(3) O1 C8 C9 C10 . . . . 75.4(3) O1 C8 C9 H9 . . . . -171(2) C7 C8 C9 O2 . . . . 71.4(3) C7 C8 C9 C10 . . . . -164.1(3) C7 C8 C9 H9 . . . . -50(2) H8 C8 C9 O2 . . . . -172(3) H8 C8 C9 C10 . . . . -48(3) H8 C8 C9 H9 . . . . 66(3) O2 C9 C10 O3 . . . . 178.7(3) O2 C9 C10 O4 . . . . -4.8(5) C8 C9 C10 O3 . . . . 57.4(4) C8 C9 C10 O4 . . . . -126.1(4) H9 C9 C10 O3 . . . . -58(2) H9 C9 C10 O4 . . . . 119(2) 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_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H001 O2w . . 2_674 0.91(3) 1.84(3) 2.694(4) 156(3) N2 H002 O3 . . 4_646 0.91(2) 1.92(2) 2.765(3) 153(4) O1 H01 O2 . . . 0.90(2) 2.19(5) 2.654(3) 111(5) O2 H02 O1w . . 1_655 0.88(2) 1.80(2) 2.674(3) 170(3) O1w H11w O3 . . . 0.91(3) 1.90(2) 2.798(3) 167(4) O1w H12w O4 . . 4_646 0.90(3) 1.86(3) 2.752(3) 168(3) O2w H21w O4 . . 4_746 0.90(3) 1.88(2) 2.706(3) 151(3) O2w H22w O3 . . 4_646 0.90(3) 1.86(3) 2.759(3) 176(4) #=end=================================================================== # Attachment 'verdan-8.cif' data_verdan-8 _database_code_depnum_ccdc_archive 'CCDC 683805' #----- 2R,3S-8 ------------------------------------------------------ _audit_creation_date 2005-09-06 _audit_creation_method from_xtal_archive_file_using_CIFIO _audit_update_record 2007-09-19 _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.0.1 _chemical_formula_moiety 'C11 H12 N2 O4' _chemical_formula_sum 'C11 H12 N2 O4' _chemical_formula_weight 236.3 _chemical_absolute_configuration syn _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z _cell_length_a 10.5317(8) _cell_length_b 10.5831(9) _cell_length_c 9.4968(10) _cell_angle_alpha 90.00000 _cell_angle_beta 90.00000 _cell_angle_gamma 90.00000 _cell_volume 1058.49(16) _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_meas not_measured _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 4.1 _cell_measurement_theta_max 26.8 _cell_measurement_temperature 200 _exptl_absorpt_coefficient_mu .115 _exptl_crystal_F_000 496 _exptl_crystal_description prism _exptl_crystal_size_max .23 _exptl_crystal_size_mid .21 _exptl_crystal_size_min .10 _exptl_crystal_colour colorless _diffrn_measurement_device_type 'Stoe Ipds' _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 6 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'XRED; Stoe & Cie, 1999' _exptl_absorpt_correction_T_min .9756 _exptl_absorpt_correction_T_max .9915 _diffrn_reflns_number 14185 _reflns_number_total 2289 _reflns_number_gt 1414 _reflns_threshold_expression 'refl observed if Fo > 3.99 \s(Fo)' _diffrn_reflns_theta_max 26.8 _diffrn_reflns_theta_full 26.8 _diffrn_measured_fraction_theta_max 1.0 _diffrn_measured_fraction_theta_full 1.0 _reflns_Friedel_coverage .859 _diffrn_reflns_av_R_equivalents .061 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_standards_decay_% 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .031 _refine_ls_wR_factor_ref .030 _refine_ls_goodness_of_fit_ref 1.38(3) _refine_ls_number_reflns 1757 _refine_ls_number_parameters 172 _refine_ls_weighting_scheme calc _refine_ls_weighting_details \w=1/[\s^2^(Fo)+0.0002(Fo^2^)] _refine_ls_hydrogen_treatment noref _refine_ls_shift/su_max .0012 _refine_diff_density_max .311 _refine_diff_density_min -.345 _refine_ls_extinction_method none _refine_ls_abs_structure_details Flack_xabs_not_refined _refine_ls_abs_structure_Flack 0 _publ_section_exptl_refinement ; The Flack parameter was fixed to 0.0 ; _computing_data_collection 'EXPOSE (Stoe & Cie, 1999)' _computing_cell_refinement 'CELL (Stoe & Cie, 1999)' _computing_data_reduction 'XRED (Stoe & Cie, 1999)' _computing_structure_solution SIR97 _computing_structure_refinement xtal_CRYLSQ _computing_molecular_graphics xtal_gx3 _computing_publication_material xtal_CIFIO loop_ _atom_type_symbol _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .002 .002 H Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 0 0 N Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .004 .003 O Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .008 .006 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 .6389(3) .4632(3) .5715(3) .0281(15) 1.00000 Uani O2 .7462(4) .4003(4) .3074(3) .0373(18) 1.00000 Uani O3 .9389(3) .1835(3) .4983(3) .0350(16) 1.00000 Uani O4 .9815(3) .3234(3) .3286(3) .0343(16) 1.00000 Uani N1 .7110(4) .2428(3) .7376(4) .0226(17) 1.00000 Uani N2 .8949(3) .3341(3) .7694(3) .0231(17) 1.00000 Uani C1 .7672(4) .1832(4) .8519(4) .024(3) 1.00000 Uani C2 .7264(4) .0832(4) .9363(5) .029(3) 1.00000 Uani C3 .8070(5) .0475(4) 1.0437(5) .035(3) 1.00000 Uani C4 .9231(5) .1078(4) 1.0676(5) .034(3) 1.00000 Uani C5 .9646(5) .2053(4) .9820(5) .032(3) 1.00000 Uani C6 .8836(4) .2417(4) .8734(4) .023(2) 1.00000 Uani C7 .7899(4) .3318(4) .6905(4) .022(2) 1.00000 Uani C8 .7611(4) .4094(4) .5611(5) .024(2) 1.00000 Uani C9 .7762(4) .3272(4) .4267(4) .0243(19) 1.00000 Uani C10 .9104(4) .2715(4) .4177(4) .023(2) 1.00000 Uani C11 1.0049(4) .4172(4) .7533(6) .032(3) 1.00000 Uani H001 .629(5) .224(4) .712(5) .04000 1.00000 Uiso H01 .576(5) .403(4) .540(5) .04000 1.00000 Uiso H02 .817(5) .413(4) .270(5) .04000 1.00000 Uiso H2 .64566 .04120 .91983 .04000 1.00000 Uiso H3 .78243 -.02207 1.10549 .04000 1.00000 Uiso H4 .97729 .08018 1.14567 .04000 1.00000 Uiso H5 1.04576 .24616 .99788 .04000 1.00000 Uiso H8 .82208 .47990 .55518 .04000 1.00000 Uiso H10 .71556 .25741 .43116 .04000 1.00000 Uiso H111 1.0129(15) .4425(19) .654(3) .04000 1.00000 Uiso H112 .9937(14) .4916(19) .812(3) .04000 1.00000 Uiso H113 1.0812(16) .3727(14) .782(3) .04000 1.00000 Uiso 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 .0215(16) .0277(14) .0351(15) .0063(13) -.0012(14) -.0034(16) O2 .0278(18) .0552(19) .0288(16) .0102(16) .0014(14) .0128(14) O3 .0328(18) .0344(15) .0377(15) .0078(16) .0012(15) .0086(17) O4 .0264(17) .0373(16) .0391(15) .0054(15) .0060(14) .0059(16) N1 .0173(18) .0244(16) .0261(17) -.0016(15) -.0008(16) .0000(17) N2 .0210(18) .0241(16) .0241(16) -.0029(15) -.0024(14) -.0002(16) C1 .025(3) .025(2) .0220(18) .0040(19) .0025(17) -.0020(18) C2 .031(3) .0259(19) .030(2) .0022(19) .007(3) -.0030(19) C3 .045(3) .026(3) .033(3) .006(3) .007(3) .006(2) C4 .040(3) .032(3) .029(3) .007(3) -.008(3) -.001(3) C5 .036(3) .031(3) .030(3) .001(2) -.005(3) -.0007(19) C6 .026(3) .0217(19) .0221(18) -.000(2) -.0006(18) -.0000(18) C7 .022(3) .0202(19) .0243(18) -.0007(19) .0018(18) -.0056(18) C8 .023(3) .0240(18) .0263(19) -.0006(18) -.0016(19) .0007(18) C9 .022(3) .0272(19) .0237(17) .0009(19) -.0019(19) .002(2) C10 .023(3) .027(2) .0193(17) -.0033(17) -.0016(19) -.0052(19) C11 .026(3) .035(3) .036(3) -.0081(18) -.0060(19) .006(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance O1 C8 . . 1.410(5) O1 H01 . . .97(5) O2 C9 . . 1.407(5) O2 H02 . . .84(5) O3 C10 . . 1.243(5) O4 C10 . . 1.256(5) N1 C1 . . 1.388(5) N1 C7 . . 1.333(5) N1 H001 . . .91(5) N2 C6 . . 1.395(5) N2 C7 . . 1.335(5) N2 C11 . . 1.463(5) C1 C2 . . 1.396(6) C1 C6 . . 1.388(6) C2 C3 . . 1.379(6) C3 C4 . . 1.399(7) C4 C5 . . 1.385(6) C5 C6 . . 1.393(6) C7 C8 . . 1.509(6) C8 C9 . . 1.553(6) C9 C10 . . 1.534(6) C11 H111 . . .98(3) C11 H112 . . .97(3) C11 H113 . . .971(18) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle C8 O1 H01 . . . 110(3) C9 O2 H02 . . . 103(3) C1 N1 C7 . . . 108.5(4) C1 N1 H001 . . . 121(3) C7 N1 H001 . . . 130(3) C6 N2 C7 . . . 108.3(4) C6 N2 C11 . . . 124.3(4) C7 N2 C11 . . . 127.5(4) N1 C1 C2 . . . 131.5(4) N1 C1 C6 . . . 106.8(4) C2 C1 C6 . . . 121.7(4) C1 C2 C3 . . . 116.3(4) C2 C3 C4 . . . 122.2(4) C3 C4 C5 . . . 121.4(4) C4 C5 C6 . . . 116.6(4) N2 C6 C1 . . . 106.5(4) N2 C6 C5 . . . 131.7(4) C1 C6 C5 . . . 121.8(4) N1 C7 N2 . . . 109.9(4) N1 C7 C8 . . . 122.2(4) N2 C7 C8 . . . 127.8(4) O1 C8 C7 . . . 110.3(4) O1 C8 C9 . . . 112.1(4) C7 C8 C9 . . . 110.1(3) O2 C9 C8 . . . 109.3(4) O2 C9 C10 . . . 111.9(4) C8 C9 C10 . . . 110.8(3) O3 C10 O4 . . . 126.8(4) O3 C10 C9 . . . 118.5(4) O4 C10 C9 . . . 114.8(4) N2 C11 H111 . . . 109.4(11) N2 C11 H112 . . . 109.4(11) N2 C11 H113 . . . 109.5(10) H111 C11 H112 . . . 109.6(18) H111 C11 H113 . . . 109.4(17) H112 C11 H113 . . . 109.5(16) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion H01 O1 C8 C7 . . . . -84(3) H01 O1 C8 C9 . . . . 39(3) H02 O2 C9 C8 . . . . 107(3) H02 O2 C9 C10 . . . . -16(3) C7 N1 C1 C2 . . . . -178.5(4) C7 N1 C1 C6 . . . . .9(4) H001 N1 C1 C2 . . . . 7(3) H001 N1 C1 C6 . . . . -173(3) C1 N1 C7 N2 . . . . -.6(5) C1 N1 C7 C8 . . . . 176.3(4) H001 N1 C7 N2 . . . . 173(4) H001 N1 C7 C8 . . . . -10(4) C7 N2 C6 C1 . . . . .6(4) C7 N2 C6 C5 . . . . -179.7(5) C11 N2 C6 C1 . . . . -179.4(4) C11 N2 C6 C5 . . . . .4(7) C6 N2 C7 N1 . . . . .0(5) C6 N2 C7 C8 . . . . -176.6(4) C11 N2 C7 N1 . . . . 179.9(4) C11 N2 C7 C8 . . . . 3.3(7) C6 N2 C11 H111 . . . . 152.3(12) C6 N2 C11 H112 . . . . -87.6(14) C6 N2 C11 H113 . . . . 32.4(16) C7 N2 C11 H111 . . . . -27.6(13) C7 N2 C11 H112 . . . . 92.5(14) C7 N2 C11 H113 . . . . -147.5(15) N1 C1 C2 C3 . . . . -179.5(4) C6 C1 C2 C3 . . . . 1.1(6) N1 C1 C6 N2 . . . . -.9(4) N1 C1 C6 C5 . . . . 179.3(4) C2 C1 C6 N2 . . . . 178.6(4) C2 C1 C6 C5 . . . . -1.2(6) C1 C2 C3 C4 . . . . .2(6) C2 C3 C4 C5 . . . . -1.5(7) C3 C4 C5 C6 . . . . 1.4(6) C4 C5 C6 N2 . . . . -179.8(4) C4 C5 C6 C1 . . . . -.1(6) N1 C7 C8 O1 . . . . 51.7(5) N1 C7 C8 C9 . . . . -72.5(5) N2 C7 C8 O1 . . . . -132.0(4) N2 C7 C8 C9 . . . . 103.7(5) O1 C8 C9 O2 . . . . 55.5(4) O1 C8 C9 C10 . . . . 179.3(3) C7 C8 C9 O2 . . . . 178.7(4) C7 C8 C9 C10 . . . . -57.5(4) O2 C9 C10 O3 . . . . -164.0(4) O2 C9 C10 O4 . . . . 17.2(5) C8 C9 C10 O3 . . . . 73.7(5) C8 C9 C10 O4 . . . . -105.1(4) 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_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O2 H02 O4 . . . 0.84(4) 2.05(4) 2.616(4) 124(4) N1 H001 O4 . . 3_456 0.91(4) 1.68(4) 2.594(4) 175(4) O1 H01 O3 . . 3_456 0.97(4) 1.75(4) 2.700(4) 167(4) #=END==============================================================