#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013179.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2013179 loop_ _publ_author_name 'Calder\'on, Angela I.' 'Terreaux, Christian' 'Gupta, Mahabir P.' 'Hostettmann, Kurt' 'Schenk, Kurt J.' _publ_section_title ; Taxiphyllin from Henriettella fascicularis ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o174 _journal_page_last o176 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C14 H17 N O7 , 2H2 O' _chemical_formula_sum 'C14 H21 N O9' _chemical_formula_weight 347.32 _chemical_melting_point 409 _chemical_name_common dhurrin _chemical_name_systematic ; (2R)-\a-(\b-D-Glucopyranosyloxy)-4-hydroxybenzeneacetonitrile dihydrate ; _space_group_IT_number 5 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'C 2y' _symmetry_space_group_name_H-M 'C 1 2 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 109.299(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.055(4) _cell_length_b 6.2858(17) _cell_length_c 16.895(5) _cell_measurement_reflns_used 754 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.91 _cell_measurement_theta_min 2.57 _cell_volume 1609.2(8) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'SHELXTL (Siemens, 1996)' _computing_publication_material 'SHELXTL and PLATON (Spek, 2001)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.058 _diffrn_reflns_av_sigmaI/netI 0.097 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 3421 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.57 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method none _exptl_crystal_description lath _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.17 _refine_diff_density_min -0.15 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.842 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 234 _refine_ls_number_reflns 1551 _refine_ls_number_restraints 7 _refine_ls_restrained_S_all 0.840 _refine_ls_R_factor_all 0.061 _refine_ls_R_factor_gt 0.033 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_gt 0.043 _refine_ls_wR_factor_ref 0.047 _reflns_number_gt 1049 _reflns_number_total 1551 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ln1156.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2' _cod_database_code 2013179 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol O1 0.21942(14) 1.0239(4) 0.23026(12) 0.0326(6) Uani d . 1 O O2 0.24078(14) 0.7259(4) 0.31082(12) 0.0314(6) Uani d . 1 O O3 0.24867(16) 0.5232(4) 0.46412(13) 0.0485(7) Uani d . 1 O H3O 0.2937 0.4864 0.5014 0.073 Uiso calc R 1 H O4 0.43406(15) 0.3770(4) 0.39617(14) 0.0418(6) Uani d . 1 O H4O 0.4225 0.3095 0.4328 0.063 Uiso calc R 1 H O5 0.50862(14) 0.7739(4) 0.36573(14) 0.0373(6) Uani d . 1 O H5O 0.5440 0.6783 0.3676 0.056 Uiso calc R 1 H O6 0.39185(16) 0.9918(4) 0.22364(14) 0.0443(7) Uani d . 1 O H6O 0.4433 0.9603 0.2304 0.066 Uiso calc R 1 H O7 0.1490(2) 0.8818(4) -0.15585(13) 0.0543(8) Uani d . 1 O H7O 0.1433 0.7564 -0.1700 0.081 Uiso calc R 1 H O1W 0.09012(18) 0.5805(5) 0.48741(17) 0.0553(8) Uani d D 1 O H11W 0.1353(11) 0.531(6) 0.482(2) 0.083 Uiso d D 1 H H12W 0.0472(13) 0.522(6) 0.4539(19) 0.083 Uiso d D 1 H O2W 0.6178(2) 0.4254(4) 0.3809(2) 0.0627(9) Uani d D 1 O H22W 0.581(2) 0.342(5) 0.386(3) 0.094 Uiso d D 1 H H21W 0.651(2) 0.362(5) 0.361(2) 0.094 Uiso d D 1 H N 0.0492(2) 1.3428(7) 0.18401(18) 0.0650(12) Uani d . 1 N C1 0.0847(3) 1.1895(7) 0.1784(2) 0.0419(11) Uani d . 1 C C2 0.1313(2) 0.9954(6) 0.17032(18) 0.0349(9) Uani d . 1 C H2 0.1033 0.8727 0.1870 0.042 Uiso calc R 1 H C3 0.1324(2) 0.9623(6) 0.08199(19) 0.0322(9) Uani d . 1 C C4 0.1117(2) 0.7675(6) 0.04304(19) 0.0390(10) Uani d . 1 C H4 0.0947 0.6561 0.0706 0.047 Uiso calc R 1 H C5 0.1158(2) 0.7355(6) -0.0371(2) 0.0433(10) Uani d . 1 C H5 0.1019 0.6036 -0.0631 0.052 Uiso calc R 1 H C6 0.1408(2) 0.9025(6) -0.0775(2) 0.0373(9) Uani d . 1 C C7 0.1607(2) 1.0987(6) -0.0396(2) 0.0409(10) Uani d . 1 C H7 0.1770 1.2107 -0.0673 0.049 Uiso calc R 1 H C8 0.1562(2) 1.1279(6) 0.0397(2) 0.0406(10) Uani d . 1 C H8 0.1693 1.2605 0.0652 0.049 Uiso calc R 1 H C1A 0.2688(2) 0.8345(6) 0.25021(18) 0.0293(9) Uani d . 1 C H1A 0.2592 0.7466 0.2001 0.035 Uiso calc R 1 H C2A 0.3651(2) 0.8951(6) 0.28808(18) 0.0279(8) Uani d . 1 C H2A 0.3718 0.9982 0.3333 0.034 Uiso calc R 1 H C3A 0.4209(2) 0.6991(5) 0.3236(2) 0.0283(9) Uani d . 1 C H3A 0.4220 0.6087 0.2767 0.034 Uiso calc R 1 H C4A 0.3843(2) 0.5705(5) 0.37996(19) 0.0280(8) Uani d . 1 C H4A 0.3924 0.6471 0.4325 0.034 Uiso calc R 1 H C5A 0.2868(2) 0.5256(5) 0.33529(18) 0.0289(8) Uani d . 1 C H5A 0.2805 0.4414 0.2848 0.035 Uiso calc R 1 H C6A 0.2417(2) 0.4098(6) 0.38847(19) 0.0383(9) Uani d . 1 C H6AB 0.1798 0.3903 0.3562 0.046 Uiso calc R 1 H H6AA 0.2680 0.2701 0.4028 0.046 Uiso calc R 1 H 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 0.0307(13) 0.0321(16) 0.0303(12) 0.0082(13) 0.0037(11) 0.0005(12) O2 0.0292(14) 0.0326(15) 0.0341(13) 0.0062(12) 0.0126(11) 0.0092(12) O3 0.0436(17) 0.071(2) 0.0347(14) 0.0104(16) 0.0177(12) 0.0063(15) O4 0.0417(16) 0.0355(16) 0.0517(16) 0.0114(14) 0.0201(13) 0.0152(13) O5 0.0239(14) 0.0395(17) 0.0435(14) 0.0010(12) 0.0043(12) -0.0033(13) O6 0.0397(16) 0.0499(18) 0.0506(15) 0.0076(15) 0.0246(13) 0.0198(13) O7 0.092(2) 0.0439(17) 0.0315(14) 0.0010(18) 0.0262(14) -0.0029(13) O1W 0.0359(16) 0.062(2) 0.067(2) -0.0001(16) 0.0158(15) -0.0186(16) O2W 0.058(2) 0.057(2) 0.087(2) 0.0142(16) 0.0419(18) 0.0159(18) N 0.063(3) 0.086(3) 0.049(2) 0.041(2) 0.0228(18) 0.010(2) C1 0.034(2) 0.063(3) 0.028(2) 0.017(2) 0.0102(17) 0.005(2) C2 0.028(2) 0.048(3) 0.0304(19) 0.002(2) 0.0118(16) 0.0065(17) C3 0.029(2) 0.038(2) 0.0264(19) 0.0020(17) 0.0051(16) -0.0005(17) C4 0.042(2) 0.038(3) 0.037(2) -0.003(2) 0.0133(18) 0.006(2) C5 0.058(3) 0.030(2) 0.040(2) -0.005(2) 0.0136(19) -0.0043(19) C6 0.041(2) 0.036(3) 0.032(2) 0.003(2) 0.0086(18) 0.002(2) C7 0.058(3) 0.036(3) 0.032(2) -0.005(2) 0.019(2) 0.0012(18) C8 0.051(3) 0.036(2) 0.034(2) -0.007(2) 0.0129(19) -0.0036(18) C1A 0.032(2) 0.036(3) 0.0206(18) 0.0034(18) 0.0101(16) -0.0005(16) C2A 0.029(2) 0.031(2) 0.0245(18) 0.0018(18) 0.0096(16) 0.0013(16) C3A 0.025(2) 0.030(2) 0.0289(18) -0.0005(17) 0.0085(15) -0.0053(17) C4A 0.031(2) 0.025(2) 0.0260(18) 0.0050(17) 0.0071(16) 0.0000(17) C5A 0.028(2) 0.031(2) 0.0270(18) 0.0036(19) 0.0081(15) 0.0027(17) C6A 0.028(2) 0.042(2) 0.041(2) 0.0004(19) 0.0062(18) 0.008(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1A O1 C2 113.8(3) C1A O2 C5A 111.7(2) C6A O3 H3O 109.5 C4A O4 H4O 109.5 C3A O5 H5O 109.5 C2A O6 H6O 109.5 C6 O7 H7O 109.5 H11W O1W H12W 108.9(12) H22W O2W H21W 109.3(13) N C1 C2 178.8(4) O1 C2 C1 104.0(3) O1 C2 C3 112.3(3) C1 C2 C3 112.4(3) O1 C2 H2 109.3 C1 C2 H2 109.3 C3 C2 H2 109.3 C4 C3 C8 119.1(3) C4 C3 C2 120.9(3) C8 C3 C2 120.0(3) C3 C4 C5 120.8(4) C3 C4 H4 119.6 C5 C4 H4 119.6 C6 C5 C4 119.0(4) C6 C5 H5 120.5 C4 C5 H5 120.5 C7 C6 O7 116.7(3) C7 C6 C5 120.7(3) O7 C6 C5 122.5(3) C8 C7 C6 119.5(4) C8 C7 H7 120.2 C6 C7 H7 120.2 C7 C8 C3 120.9(3) C7 C8 H8 119.6 C3 C8 H8 119.6 O1 C1A O2 106.9(2) O1 C1A C2A 107.7(3) O2 C1A C2A 109.8(2) O1 C1A H1A 110.8 O2 C1A H1A 110.8 C2A C1A H1A 110.8 O6 C2A C1A 107.8(2) O6 C2A C3A 111.0(3) C1A C2A C3A 110.4(3) O6 C2A H2A 109.2 C1A C2A H2A 109.2 C3A C2A H2A 109.2 O5 C3A C4A 112.8(3) O5 C3A C2A 106.5(3) C4A C3A C2A 112.4(3) O5 C3A H3A 108.4 C4A C3A H3A 108.4 C2A C3A H3A 108.4 O4 C4A C3A 105.5(3) O4 C4A C5A 110.8(3) C3A C4A C5A 109.7(2) O4 C4A H4A 110.2 C3A C4A H4A 110.2 C5A C4A H4A 110.2 O2 C5A C6A 106.8(2) O2 C5A C4A 108.9(3) C6A C5A C4A 114.2(2) O2 C5A H5A 109.0 C6A C5A H5A 109.0 C4A C5A H5A 109.0 O3 C6A C5A 112.2(3) O3 C6A H6AB 109.2 C5A C6A H6AB 109.2 O3 C6A H6AA 109.2 C5A C6A H6AA 109.2 H6AB C6A H6AA 107.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1A 1.409(4) O1 C2 1.453(4) O2 C1A 1.422(3) O2 C5A 1.449(4) O3 C6A 1.435(4) O3 H3O 0.8200 O4 C4A 1.431(4) O4 H4O 0.8200 O5 C3A 1.431(4) O5 H5O 0.8200 O6 C2A 1.431(3) O6 H6O 0.8200 O7 C6 1.379(4) O7 H7O 0.8200 O1W H11W 0.822(5) O1W H12W 0.820(5) O2W H22W 0.821(5) O2W H21W 0.823(5) N C1 1.139(5) C1 C2 1.462(5) C2 C3 1.512(4) C2 H2 0.9800 C3 C4 1.378(5) C3 C8 1.386(5) C4 C5 1.392(4) C4 H4 0.9300 C5 C6 1.382(5) C5 H5 0.9300 C6 C7 1.378(5) C7 C8 1.377(4) C7 H7 0.9300 C8 H8 0.9300 C1A C2A 1.513(4) C1A H1A 0.9800 C2A C3A 1.525(5) C2A H2A 0.9800 C3A C4A 1.508(4) C3A H3A 0.9800 C4A C5A 1.523(4) C4A H4A 0.9800 C5A C6A 1.514(4) C5A H5A 0.9800 C6A H6AB 0.9700 C6A H6AA 0.9700 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O3 H3O O2W 2_454 0.97 1.92 2.849(4) 159 O4 H4O O1W 4_344 0.97 1.89 2.828(3) 164 O5 H5O O2W . 0.97 1.81 2.764(4) 170 O6 H6O N 3_545 0.97 2.09 2.970(4) 150 O7 H7O O6 4_343 0.97 1.75 2.694(4) 166 O1W H11W O3 . 1.01 1.78 2.725(4) 157 O1W H12W O5 3_445 1.01 1.95 2.807(3) 140 O2W H21W O2 3_545 1.01 1.89 2.901(3) 175 O2W H22W O4 . 1.01 2.29 3.060(4) 132 O2W H22W O1W 3_545 1.01 2.22 2.943(4) 127 C3A H3A O7 4_343 1.10 2.34 3.342(4) 151 O6 H6O O5 . 0.97 2.43 2.860(3) 107 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 C1A O1 C2 C1 163.5(3) C1A O1 C2 C3 -74.8(3) O1 C2 C3 C4 110.2(4) C1 C2 C3 C4 -132.9(4) O1 C2 C3 C8 -68.5(4) C1 C2 C3 C8 48.4(4) C8 C3 C4 C5 1.0(5) C2 C3 C4 C5 -177.7(3) C3 C4 C5 C6 -0.2(5) C4 C5 C6 C7 -0.6(6) C4 C5 C6 O7 178.0(3) O7 C6 C7 C8 -178.2(3) C5 C6 C7 C8 0.5(6) C6 C7 C8 C3 0.4(6) C4 C3 C8 C7 -1.1(5) C2 C3 C8 C7 177.6(3) C2 O1 C1A O2 -80.7(3) C2 O1 C1A C2A 161.4(2) C5A O2 C1A O1 179.2(2) C5A O2 C1A C2A -64.2(3) O1 C1A C2A O6 -67.5(3) O2 C1A C2A O6 176.5(3) O1 C1A C2A C3A 171.2(2) O2 C1A C2A C3A 55.1(3) O6 C2A C3A O5 66.6(3) C1A C2A C3A O5 -173.9(2) O6 C2A C3A C4A -169.5(3) C1A C2A C3A C4A -50.0(3) O5 C3A C4A O4 -69.3(3) C2A C3A C4A O4 170.4(3) O5 C3A C4A C5A 171.4(3) C2A C3A C4A C5A 51.0(3) C1A O2 C5A C6A -171.2(2) C1A O2 C5A C4A 65.1(3) O4 C4A C5A O2 -172.9(2) C3A C4A C5A O2 -56.8(3) O4 C4A C5A C6A 67.9(4) C3A C4A C5A C6A -176.1(3) O2 C5A C6A O3 -62.9(3) C4A C5A C6A O3 57.5(4)