#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/20/2002017.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_2002017 loop_ _publ_author_name 'Goddard, R.' 'Niemeyer, C. M.' 'Reetz, M. T.' _publ_contact_author ; Dr. Richard Goddard Max-Planck-Institut fuer Kohlenforschung Kaiser-Wilhelm-Platz 1 D-4330 Muelheim a.d. Ruhr Germany ; _publ_section_title ; Structure of 1,3-xylyl-(18-crown-5)--ammonium catecholborate (1/1) ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 402 _journal_page_last 404 _journal_paper_doi 10.1107/S0108270192010485 _journal_volume 49 _journal_year 1993 _chemical_formula_moiety 'C16 H24 O5, H4 N +, C12 H8 B O4 -' _chemical_formula_sum 'C28 H36 B N O9' _chemical_formula_weight 541.4 _chemical_name_systematic ' 1,3-Xylyl-(18-crown-5)-ammonium-catecholborate' _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90.000000 _cell_angle_beta 99.896(5) _cell_angle_gamma 90.000000 _cell_formula_units_Z 4 _cell_length_a 14.930(2) _cell_length_b 11.1930(10) _cell_length_c 17.2110(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 17.2 _cell_measurement_theta_min 9.5 _cell_volume 2833.4(5) _computing_cell_refinement 'LSCELD (Davis, 1969)' _computing_data_collection 'Enraf-Nonius CAD-4' _computing_data_reduction 'DATAP (Coppens, Leiserowitz & Rabinovich, 1965)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' _computing_publication_material 'DAESD (Davis & Harris, 1970)' _computing_structure_refinement 'GFLMX (modified ORFLS; Busing, Martin & Levy, 1962)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 7007 _diffrn_reflns_theta_max 27.41 _diffrn_reflns_theta_min 1.20 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.27 _exptl_crystal_description prism _exptl_crystal_F_000 1152 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.19 _refine_diff_density_min -0.73 _refine_ls_extinction_method 'not applied' _refine_ls_goodness_of_fit_obs 1.97 _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 368 _refine_ls_number_reflns 3239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.109 _refine_ls_R_factor_obs 0.060 _refine_ls_shift/esd_max 0.71 _refine_ls_shift/esd_mean 0.43 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F)]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.059 _reflns_number_observed 3239 _reflns_number_total 6448 _reflns_observed_criterion I>=2.0\s(I) _cod_data_source_file ab1034.cif _cod_data_source_block ab1034 _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(F)]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(F)]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 2833.5(4) _cod_original_sg_symbol_H-M P21/c _cod_original_formula_sum 'C28 H36 B1 N1 O9' _cod_database_code 2002017 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' 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 0.0620(10) 0.059(2) 0.0670(10) -0.0160(10) 0.0110(10) -0.0020(10) O2 0.0550(10) 0.100(2) 0.064(2) -0.0120(10) 0.0270(10) -0.0080(10) O3 0.054(2) 0.091(2) 0.065(2) 0.0160(10) 0.0120(10) 0.0090(10) O4 0.079(2) 0.0530(10) 0.077(2) 0.0100(10) 0.0260(10) 0.0020(10) O5 0.061(2) 0.063(2) 0.083(2) -0.0070(10) 0.0290(10) 0.0040(10) O6 0.0570(10) 0.0520(10) 0.0590(10) -0.0030(10) 0.0020(10) -0.0090(10) O7 0.0620(10) 0.0500(10) 0.0550(10) -0.0010(10) -0.0010(10) -0.0020(10) O8 0.0600(10) 0.0560(10) 0.0530(10) 0.0050(10) 0.0240(10) 0.0050(10) O9 0.0570(10) 0.0570(10) 0.0560(10) 0.0110(10) 0.0230(10) 0.0070(10) N 0.045(2) 0.058(2) 0.052(2) -0.001(2) 0.013(2) 0.006(2) C1 0.094(3) 0.048(2) 0.073(2) 0.006(2) 0.007(2) 0.001(2) C2 0.084(3) 0.076(3) 0.080(3) -0.036(2) 0.009(2) 0.012(2) C3 0.069(3) 0.129(4) 0.062(2) -0.046(3) 0.019(2) 0.009(3) C4 0.050(2) 0.140(4) 0.075(3) -0.034(3) 0.030(2) -0.047(3) C5 0.041(2) 0.139(4) 0.079(3) 0.022(3) 0.007(2) -0.033(3) C6 0.082(3) 0.124(4) 0.079(3) 0.049(3) 0.027(2) 0.026(3) C7 0.119(4) 0.061(3) 0.093(3) 0.037(3) 0.049(3) 0.023(2) C8 0.114(4) 0.045(2) 0.096(3) -0.007(2) 0.030(3) -0.008(2) C9 0.079(3) 0.069(3) 0.096(3) -0.028(2) 0.025(2) 0.009(2) C10 0.050(2) 0.093(3) 0.114(3) -0.008(2) 0.033(2) 0.005(3) C11 0.045(2) 0.076(3) 0.081(2) 0.010(2) 0.023(2) 0.001(2) C12 0.043(2) 0.115(4) 0.095(3) 0.006(2) 0.009(2) -0.011(3) C13 0.072(3) 0.116(4) 0.085(3) 0.032(3) -0.010(2) 0.010(3) C14 0.085(3) 0.077(3) 0.076(3) 0.023(3) 0.007(2) 0.012(2) C15 0.066(2) 0.059(2) 0.058(2) 0.017(2) 0.008(2) -0.003(2) C16 0.048(2) 0.063(2) 0.069(2) 0.018(2) 0.013(2) 0.005(2) C17 0.052(2) 0.049(2) 0.051(2) -0.003(2) 0.017(2) -0.001(2) C18 0.072(3) 0.051(2) 0.074(2) -0.009(2) 0.021(2) -0.011(2) C19 0.100(3) 0.042(2) 0.091(3) 0.003(2) 0.040(3) 0.005(2) C20 0.082(3) 0.061(3) 0.065(2) 0.018(2) 0.028(2) 0.017(2) C21 0.063(2) 0.068(3) 0.048(2) 0.010(2) 0.011(2) 0.004(2) C22 0.058(2) 0.044(2) 0.045(2) 0.001(2) 0.021(2) 0.001(2) C23 0.052(2) 0.050(2) 0.041(2) 0.002(2) 0.0070(10) -0.003(2) C24 0.074(2) 0.068(3) 0.059(2) 0.012(2) 0.018(2) -0.007(2) C25 0.103(3) 0.057(3) 0.070(3) 0.030(2) 0.006(2) -0.009(2) C26 0.111(3) 0.048(2) 0.061(2) 0.001(2) 0.001(2) 0.003(2) C27 0.074(2) 0.059(2) 0.050(2) -0.008(2) 0.010(2) 0.002(2) C28 0.050(2) 0.052(2) 0.039(2) -0.003(2) 0.0070(10) -0.003(2) B 0.048(2) 0.055(3) 0.047(2) 0.001(2) 0.011(2) -0.001(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O1 0.75940(10) -0.3403(2) 0.86950(10) 0.063(2) Uani d . O2 0.59470(10) -0.2134(2) 0.83550(10) 0.071(2) Uani d . O3 0.6096(2) 0.0396(2) 0.81720(10) 0.070(2) Uani d . O4 0.7699(2) 0.1488(2) 0.79030(10) 0.068(2) Uani d . O5 0.93420(10) 0.0268(2) 0.83710(10) 0.067(2) Uani d . O6 0.72890(10) 0.1140(2) 0.11840(10) 0.0570(10) Uani d . O7 0.62310(10) 0.0243(2) 0.01990(10) 0.0570(10) Uani d . O8 0.77330(10) -0.0679(2) 0.05570(10) 0.0550(10) Uani d . O9 0.66930(10) -0.0847(2) 0.14280(10) 0.0550(10) Uani d . N 0.7700(2) -0.0765(3) -0.1090(2) 0.051(2) Uani d . C1 0.8267(3) -0.4105(3) 0.8421(2) 0.072(3) Uani d . C2 0.6729(3) -0.3955(4) 0.8594(2) 0.080(3) Uani d . C3 0.6079(3) -0.3134(5) 0.8870(2) 0.086(3) Uani d . C4 0.5308(2) -0.1298(4) 0.8550(2) 0.086(3) Uani d . C5 0.5270(2) -0.0272(5) 0.8004(2) 0.087(3) Uani d . C6 0.6096(3) 0.1429(5) 0.7722(2) 0.093(3) Uani d . C7 0.6911(3) 0.2144(4) 0.8006(2) 0.087(3) Uani d . C8 0.8513(3) 0.2093(3) 0.8160(2) 0.084(3) Uani d . C9 0.9288(3) 0.1378(4) 0.7973(2) 0.080(3) Uani d . C10 1.0080(2) -0.0444(4) 0.8212(2) 0.083(3) Uani d . C11 1.0014(2) -0.1660(3) 0.8553(2) 0.066(3) Uani d . C12 1.0689(2) -0.2123(5) 0.9126(3) 0.085(3) Uani d . C13 1.0602(3) -0.3241(5) 0.9428(3) 0.094(3) Uani d . C14 0.9832(3) -0.3887(4) 0.9186(2) 0.080(3) Uani d . C15 0.9141(2) -0.3450(3) 0.8631(2) 0.061(2) Uani d . C16 0.9252(2) -0.2347(3) 0.8298(2) 0.060(2) Uani d . C17 0.6797(2) 0.1981(3) 0.0723(2) 0.050(2) Uani d . C18 0.6869(2) 0.3192(3) 0.0790(2) 0.065(3) Uani d . C19 0.6262(3) 0.3873(3) 0.0273(3) 0.075(3) Uani d . C20 0.5607(3) 0.3358(3) -0.0287(2) 0.068(3) Uani d . C21 0.5542(2) 0.2111(3) -0.0358(2) 0.059(2) Uani d . C22 0.6154(2) 0.1452(3) 0.0140(2) 0.047(2) Uani d . C23 0.7774(2) -0.1795(3) 0.0887(2) 0.048(2) Uani d . C24 0.8326(2) -0.2724(3) 0.0766(2) 0.066(3) Uani d . C25 0.8221(3) -0.3780(3) 0.1168(2) 0.078(3) Uani d . C26 0.7597(3) -0.3881(3) 0.1666(2) 0.075(3) Uani d . C27 0.7052(2) -0.2932(3) 0.1788(2) 0.061(2) Uani d . C28 0.7149(2) -0.1882(3) 0.1398(2) 0.047(2) Uani d . B 0.6980(2) -0.0025(4) 0.0850(2) 0.050(2) Uani d . H1 0.767(2) -0.164(4) -0.124(2) 0.100(10) Uiso d N H2 0.821(2) -0.053(3) -0.123(2) 0.070(10) Uiso d N H3 0.724(2) -0.040(3) -0.131(2) 0.060(10) Uiso d N H4 0.774(2) -0.070(3) -0.057(2) 0.060(10) Uiso d N H1a 0.8109 -0.4248 0.7851 0.050 Uiso calc C1 H1b 0.8291 -0.4918 0.8649 0.050 Uiso calc C1 H2a 0.6774 -0.4752 0.8827 0.050 Uiso calc C2 H2b 0.6518 -0.4116 0.8021 0.050 Uiso calc C2 H3a 0.5522 -0.3548 0.8945 0.050 Uiso calc C3 H3b 0.6352 -0.2900 0.9430 0.050 Uiso calc C3 H4a 0.5522 -0.0943 0.9088 0.050 Uiso calc C4 H4b 0.4724 -0.1621 0.8580 0.050 Uiso calc C4 H5a 0.5204 -0.0645 0.7447 0.050 Uiso calc C5 H5b 0.4725 0.0196 0.7963 0.050 Uiso calc C5 H6a 0.5543 0.1923 0.7682 0.050 Uiso calc C6 H6b 0.6123 0.1266 0.7151 0.050 Uiso calc C6 H7a 0.6912 0.2959 0.7814 0.050 Uiso calc C7 H7b 0.6926 0.2282 0.8600 0.050 Uiso calc C7 H8a 0.8619 0.2165 0.8763 0.050 Uiso calc C8 H8b 0.8505 0.2917 0.7998 0.050 Uiso calc C8 H9a 0.9142 0.1247 0.7377 0.050 Uiso calc C9 H9b 0.9850 0.1816 0.8037 0.050 Uiso calc C9 H10a 1.0660 -0.0057 0.8354 0.050 Uiso calc C10 H10b 1.0029 -0.0504 0.7601 0.050 Uiso calc C10 H12 1.1249 -0.1613 0.9311 0.050 Uiso calc C12 H13 1.1100 -0.3551 0.9840 0.050 Uiso calc C13 H14 0.9782 -0.4699 0.9406 0.050 Uiso calc C14 H16 0.8770 -0.2064 0.7868 0.050 Uiso calc C16 H18 0.7329 0.3570 0.1193 0.050 Uiso calc C18 H19 0.6270 0.4730 0.0286 0.050 Uiso calc C19 H20 0.5158 0.3846 -0.0662 0.050 Uiso calc C20 H21 0.5069 0.1717 -0.0784 0.050 Uiso calc C21 H24 0.8782 -0.2650 0.0399 0.050 Uiso calc C24 H25 0.8624 -0.4471 0.1095 0.050 Uiso calc C25 H26 0.7556 -0.4665 0.1922 0.050 Uiso calc C26 H27 0.6603 -0.3025 0.2099 0.050 Uiso calc C27 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.002 0.002 'International Tables Vol IV Table 2.2A' H 0.000 0.000 'International Tables Vol IV Table 2.2C' B 0.000 0.001 'International Tables Vol IV Table 2.2A' N 0.004 0.003 'International Tables Vol IV Table 2.2A' O 0.008 0.006 'International Tables Vol IV Table 2.2A' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 6 0 -4 0 -6 6 -2 -5 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 _geom_angle_publ_flag C2 O1 C1 . . . 113.7(3) yes C4 O2 C3 . . . 113.5(3) yes C6 O3 C5 . . . 113.9(3) yes C8 O4 C7 . . . 113.8(3) yes C10 O5 C9 . . . 112.3(3) yes B O6 C17 . . . 106.5(2) yes B O7 C22 . . . 107.6(2) yes B O8 C23 . . . 106.7(2) yes B O9 C28 . . . 107.7(2) yes H4 N H3 . . . 109(3) yes H4 N H2 . . . 110(3) yes H4 N H1 . . . 110(3) yes H3 N H2 . . . 114(3) yes H3 N H1 . . . 111(3) yes H2 N H1 . . . 103(3) yes C15 C1 O1 . . . 106.8(3) yes C3 C2 O1 . . . 109.1(3) yes C2 C3 O2 . . . 108.5(3) yes C5 C4 O2 . . . 108.5(3) yes C4 C5 O3 . . . 109.9(3) yes C7 C6 O3 . . . 110.3(3) yes C6 C7 O4 . . . 109.4(3) yes C9 C8 O4 . . . 109.7(3) yes C8 C9 O5 . . . 110.4(3) yes C11 C10 O5 . . . 109.2(3) yes C16 C11 C12 . . . 118.5(4) yes C16 C11 C10 . . . 119.3(3) yes C12 C11 C10 . . . 122.2(3) yes C13 C12 C11 . . . 120.5(4) yes C14 C13 C12 . . . 120.0(4) yes C15 C14 C13 . . . 121.2(4) yes C16 C15 C14 . . . 118.6(3) yes C16 C15 C1 . . . 120.1(3) yes C14 C15 C1 . . . 121.2(3) yes C15 C16 C11 . . . 121.1(3) yes B C17 C22 . . . 72.9(2) no B C17 C18 . . . 165.9(3) no B C17 O6 . . . 38.3(2) no C22 C17 C18 . . . 121.1(3) yes C22 C17 O6 . . . 111.2(3) yes C18 C17 O6 . . . 127.7(3) yes C19 C18 C17 . . . 117.4(3) yes C20 C19 C18 . . . 121.9(3) yes C21 C20 C19 . . . 120.5(3) yes C22 C21 C20 . . . 117.2(3) yes B C22 C21 . . . 166.6(3) no B C22 C17 . . . 71.4(2) no B C22 O7 . . . 37.9(2) no C21 C22 C17 . . . 121.9(3) yes C21 C22 O7 . . . 128.8(3) yes C17 C22 O7 . . . 109.3(3) yes B C23 C28 . . . 71.3(2) no B C23 C24 . . . 166.5(3) no B C23 O8 . . . 38.60(10) no C28 C23 C24 . . . 122.1(3) yes C28 C23 O8 . . . 109.9(3) yes C24 C23 O8 . . . 128.1(3) yes C25 C24 C23 . . . 116.7(3) yes C26 C25 C24 . . . 121.7(4) yes C27 C26 C25 . . . 120.9(3) yes C28 C27 C26 . . . 118.1(3) yes B C28 C27 . . . 165.8(3) no B C28 C23 . . . 73.3(2) no B C28 O9 . . . 38.0(2) no C27 C28 C23 . . . 120.5(3) yes C27 C28 O9 . . . 128.3(3) yes C23 C28 O9 . . . 111.2(3) yes C28 B C23 . . . 35.30(10) no C28 B C22 . . . 153.1(2) no C28 B C17 . . . 161.1(2) no C28 B O9 . . . 34.30(10) no C28 B O8 . . . 70.0(2) no C28 B O7 . . . 121.1(2) no C28 B O6 . . . 130.1(2) no C23 B C22 . . . 149.7(2) no C23 B C17 . . . 155.1(2) no C23 B O9 . . . 69.6(2) no C23 B O8 . . . 34.70(10) no C23 B O7 . . . 121.0(2) no C23 B O6 . . . 128.9(2) no C22 B C17 . . . 35.70(10) no C22 B O9 . . . 128.4(2) no C22 B O8 . . . 122.6(2) no C22 B O7 . . . 34.60(10) no C22 B O6 . . . 70.8(2) no C17 B O9 . . . 129.9(2) no C17 B O8 . . . 122.4(2) no C17 B O7 . . . 70.2(2) no C17 B O6 . . . 35.20(10) no O9 B O8 . . . 104.1(3) yes O9 B O7 . . . 111.8(3) yes O9 B O6 . . . 113.6(3) yes O8 B O7 . . . 111.0(3) yes O8 B O6 . . . 111.2(3) yes O7 B O6 . . . 105.3(3) yes 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 _geom_bond_publ_flag O1 C1 . . 1.419(5) yes O1 C2 . . 1.415(5) yes O2 C3 . . 1.421(5) yes O2 C4 . . 1.418(5) yes O3 C5 . . 1.429(5) yes O3 C6 . . 1.393(5) yes O4 C7 . . 1.425(5) yes O4 C8 . . 1.396(5) yes O5 C9 . . 1.415(5) yes O5 C10 . . 1.425(4) yes O6 C17 . . 1.362(4) yes O6 B . . 1.467(4) yes O7 C22 . . 1.361(4) yes O7 B . . 1.472(4) yes O8 C23 . . 1.369(4) yes O8 B . . 1.502(4) yes O9 C28 . . 1.349(4) yes O9 B . . 1.472(4) yes N H1 . . 1.02(4) yes N H2 . . 0.88(3) yes N H3 . . 0.83(3) yes N H4 . . 0.89(4) yes C1 C15 . . 1.488(5) yes C2 C3 . . 1.474(6) yes C4 C5 . . 1.478(7) yes C6 C7 . . 1.468(6) yes C8 C9 . . 1.487(6) yes C10 C11 . . 1.492(6) yes C11 C12 . . 1.385(6) yes C11 C16 . . 1.381(5) yes C12 C13 . . 1.371(7) yes C13 C14 . . 1.361(6) yes C14 C15 . . 1.370(5) yes C15 C16 . . 1.384(5) yes C17 C18 . . 1.364(5) yes C17 C22 . . 1.396(4) yes C17 B . . 2.268(5) no C18 C19 . . 1.385(5) yes C19 C20 . . 1.377(6) yes C20 C21 . . 1.403(5) yes C21 C22 . . 1.359(5) yes C22 B . . 2.287(5) no C23 C24 . . 1.366(5) yes C23 C28 . . 1.391(4) yes C23 B . . 2.304(5) no C24 C25 . . 1.392(5) yes C25 C26 . . 1.376(6) yes C26 C27 . . 1.375(5) yes C27 C28 . . 1.374(5) yes C28 B . . 2.279(5) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139054037