# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global #============================================================================== _journal_coden_Cambridge 188 # 0. AUDIT DETAILS _audit_creation_date 'Wed Feb 14 09:36:25 2001' _audit_creation_method 'PLATON option' _audit_update_record ; ? ; #=============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name # Name of author for correspondence ; Peter Luger ; _publ_contact_author_address # address of author for correspondence ; Institut f\"ur Chemie/Kristallographie Freie Universit\"at Berlin Takustrasse 6 D-14195 Berlin Germany ; _publ_contact_author_email 'luger@chemie.fu-berlin.de' _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_requested_journal ; Journal of the Chemical Society Perkin Trans. 2' ; # Publication choise FI FM FO CI CM CO AD _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter # Include date of submission ; Date of submission ? Please consider this CIF submission for publication as a Regular Structural Paper in Journal of the Chemical Society Perkin Trans. 2. ; #=============================================================================== # 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY) _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Experimental charge density and topological properties of 3-(tert-tutyloxycarbonylamino)bicyclo[1.1.1]pentanecarboxylic acid ; _publ_section_title_footnote ; ? ; # The loop structure below should contain the names and adresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Peter Luger' # author name ; Institut f\"ur Chemie/Kristallographie # Address of this author Freie Universit\"at Berlin Takustrasse 6 D-14195 Berlin Germany ; 'Manuela Weber' # author name ; Institut f\"ur Chemie/Kristallographie # Address of this author Freie Universit\"at Berlin Takustrasse 6 D-14195 Berlin Germany ; 'Gunter Szeimies' # author name ; Institut f\"ur Organische und Bioorganische Chemie # Address of this author Humboldt-Universit\"at zu Berlin Hessische Str. 1-2 10115 Berlin Germany ; 'Michael Patzel' # author name ; Institut f\"ur Organische und Bioorganische Chemie Humboldt-Universit\"at zu Berlin Hessische Str. 1-2 10115 Berlin Germany ; #=============================================================================== # 4. TEXT _publ_section_synopsis ; ? ; _publ_section_abstract ; ? ; # Insert blank lines between paragraphs _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; # Insert blank lines between references _publ_section_references ; ? ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; View of the title compound with the atom numbering scheme Displacement ellipsoids for non-H atoms are drawn at the 50% probability level ; #=============================================================================== data_p08e _database_code_CSD 163809 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 3-(tert-tutyloxycarbonylamino)bicyclo[1.1.1]pentane-carboxylic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H17 N O4' _chemical_formula_structural ? # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_sum 'C11 H17 N O4' _chemical_formula_weight 227.26 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 10.5109 0.3229 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 10.5109 0.3229 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 10.5109 0.3229 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 10.5109 0.3229 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C c' loop_ _symmetry_equiv_pos_as_xyz x,y,z x,-y,1/2+z 1/2+x,1/2+y,z 1/2+x,1/2-y,1/2+z _cell_length_a 6.0581 _cell_length_b 18.1774 _cell_length_c 11.2293 _cell_angle_alpha 90 _cell_angle_beta 92.9400 _cell_angle_gamma 90 _cell_volume 1234.95 _cell_formula_units_Z 4 _cell_measurement_temperature 110 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; ? ; _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.09 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type no _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w and \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 29337 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min ? _diffrn_reflns_theta_max 103.00 _diffrn_reflns_theta_full ? _diffrn_measured_fraction_theta_max ? _diffrn_measured_fraction_theta_full ? _diffrn_reflns_reduction_process ; ? ; # number of unique reflections _reflns_number_total 6786 # number of observed reflections (> n sig(I)) _reflns_number_gt 6090 _reflns_threshold_expression >3sigma(I) _computing_data_collection 'SMART (Bruker-AXS, 1996)' _computing_cell_refinement 'SMART, SAINT (Bruker-AXS, 1996, 1994)' _computing_data_reduction 'SHELXTL, SAINT (Bruker-AXS, 1996)' _computing_structure_solution ? _computing_structure_refinement 'XD (Koritsanszky et al, 1995)' _computing_molecular_graphics ; schakal88 (Keller, 1988), ortep (Johnson, 1976) ; _computing_publication_material 'PLATON (Spek, 1990)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details none _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'sigma' _refine_ls_weighting_details 'w=1/\S' _refine_ls_hydrogen_treatment 'H-atom refinement: see text ' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 999999 _refine_ls_number_reflns 6090 _refine_ls_number_parameters ? _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.027 _refine_ls_R_factor_gt 0.022 _refine_ls_wR_factor_ref ? _refine_ls_wR_factor_gt 0.018 _refine_ls_goodness_of_fit_ref 3.39 _refine_ls_restrained_S_all ? _refine_ls_shift/su_max ? _refine_ls_shift/su_mean ? _refine_diff_density_max ? _refine_diff_density_min ? _refine_diff_density_rms ? #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv O1 O Uani 0.83767(19) 0.59500(4) 1.17044(10) 1.000 0.0336(2) O2 O Uani 0.98832(13) 0.48768(3) 1.23426(7) 1.000 0.0234(1) O3 O Uani 0.45594 0.30815(3) 0.90111 1.000 0.0242(1) O4 O Uani 0.16054(15) 0.33120(3) 0.77299(9) 1.000 0.0302(2) N1 N Uani 0.29876(11) 0.41928(3) 0.90118(6) 1.000 0.0230(1) C1 C Uani 0.67232(11) 0.48727(2) 1.09510(6) 1.000 0.0176(1) C2 C Uani 0.51734(12) 0.42061(3) 1.11750(6) 1.000 0.0267(1) C3 C Uani 0.46386(10) 0.44603(2) 0.98637(6) 1.000 0.0182(1) C4 C Uani 0.46937(11) 0.52631(3) 1.03274(6) 1.000 0.0272(1) C5 C Uani 0.71729(11) 0.45220(3) 0.97236(6) 1.000 0.0268(1) C6 C Uani 0.29721(10) 0.35081(3) 0.85277(6) 1.000 0.0226(1) C7 C Uani 0.49026(11) 0.23184(3) 0.85876(6) 1.000 0.0228(1) C8 C Uani 0.68245(13) 0.20644(3) 0.94118(7) 1.000 0.0371(1) C9 C Uani 0.28674(13) 0.18491(3) 0.87717(7) 1.000 0.0300(1) C10 C Uani 0.55530(14) 0.23267(3) 0.72943(7) 1.000 0.0354(2) C11 C Uani 0.84830(11) 0.52219(3) 1.17438(6) 1.000 0.0189(1) H1 H Uiso 0.18741 0.45580 0.85943 1.000 0.016(4) H10 H Uiso 0.96599 0.61601 1.20918 1.000 0.018(4) H21 H Uiso 0.59693 0.36709 1.13003 1.000 0.037(4) H22 H Uiso 0.38756 0.43070 1.17930 1.000 0.032(3) H41 H Uiso 0.51142 0.56726 0.96655 1.000 0.028(3) H42 H Uiso 0.33307 0.54045 1.08828 1.000 0.025(3) H51 H Uiso 0.76682 0.49046 0.90374 1.000 0.043(4) H52 H Uiso 0.80737 0.40021 0.97658 1.000 0.036(3) H81 H Uiso 0.82480 0.24241 0.93274 1.000 0.034(4) H82 H Uiso 0.72655 0.15044 0.91703 1.000 0.031(3) H83 H Uiso 0.63089 0.20718 1.03294 1.000 0.033(3) H91 H Uiso 0.23233 0.18665 0.96824 1.000 0.052(4) H92 H Uiso 0.32357 0.12753 0.85773 1.000 0.037(3) H93 H Uiso 0.14792 0.20129 0.81745 1.000 0.036(3) H101 H Uiso 0.41876 0.25321 0.67157 1.000 0.039(4) H102 H Uiso 0.59446 0.17619 0.70543 1.000 0.034(4) H103 H Uiso 0.69765 0.26835 0.71846 1.000 0.046(4) loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0373(3) 0.0184(2) 0.0424(3) 0.0022(2) -0.0236(3) -0.0046(2) O2 0.0219(2) 0.0216(2) 0.0259(2) -0.0012(2) -0.0071(2) 0.0012(2) O3 0.0245(2) 0.0177(2) 0.0290(2) -0.0028(1) -0.0127(2) 0.0046(1) O4 0.0318(3) 0.0195(2) 0.0369(3) -0.0060(2) -0.0210(2) 0.0058(2) N1 0.0215(2) 0.0168(2) 0.0294(2) -0.0031(1) -0.0112(1) 0.0031(1) C1 0.0168(1) 0.0183(2) 0.0175(1) -0.0010(1) -0.0015(1) -0.0015(1) C2 0.0296(2) 0.0277(2) 0.0222(2) 0.0053(1) -0.0040(1) -0.0102(2) C3 0.0169(2) 0.0166(2) 0.0207(2) -0.0012(1) -0.0037(1) 0.0004(1) C4 0.0245(2) 0.0182(2) 0.0377(2) -0.0042(1) -0.0102(2) 0.0030(1) C5 0.0194(2) 0.0393(3) 0.0217(2) -0.0089(2) 0.0017(1) -0.0018(2) C6 0.0227(2) 0.0166(2) 0.0271(2) -0.0025(1) -0.0119(1) 0.0032(1) C7 0.0232(2) 0.0183(2) 0.0264(2) 0.0005(1) -0.0047(1) 0.0041(1) C8 0.0327(2) 0.0300(2) 0.0469(3) 0.0020(2) -0.0142(2) 0.0119(2) C9 0.0312(2) 0.0225(2) 0.0359(2) -0.0003(2) -0.0017(2) -0.0019(2) C10 0.0420(3) 0.0332(3) 0.0315(2) -0.0001(2) 0.0056(2) 0.0051(2) C11 0.0189(2) 0.0190(2) 0.0184(2) -0.0007(1) -0.0035(1) -0.0013(1) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.3257(9) . . yes O2 C11 1.2275(10) . . yes O3 C6 1.3293(7) . . yes O3 C7 1.4845(8) . . yes O4 C6 1.2406(11) . . yes O1 H10 0.9512 . . no N1 C3 1.4331(9) . . yes N1 C6 1.3580(8) . . yes N1 H1 1.0407 . . no C1 C5 1.5552(9) . . no C1 C2 1.5612(8) . . no C1 C4 1.5548(9) . . no C1 C11 1.4949(9) . . no C2 C3 1.5613(9) . . no C3 C5 1.5554(9) . . no C3 C4 1.5492(7) . . no C7 C10 1.5242(10) . . no C7 C8 1.5215(10) . . no C7 C9 1.5221(10) . . no C2 H21 1.0917 . . no C2 H22 1.0906 . . no C4 H41 1.0913 . . no C4 H42 1.0907 . . no C5 H51 1.0914 . . no C5 H52 1.0911 . . no C8 H81 1.0902 . . no C8 H82 1.0902 . . no C8 H83 1.0920 . . no C9 H91 1.0909 . . no C9 H92 1.0910 . . no C9 H93 1.0899 . . no C10 H101 1.0912 . . no C10 H102 1.0906 . . no C10 H103 1.0911 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O3 C7 121.64(4) . . . yes C11 O1 H10 110.39 . . . no C3 N1 C6 124.64(6) . . . yes C6 N1 H1 114.41 . . . no C3 N1 H1 119.89 . . . no C2 C1 C5 87.64(4) . . . no C4 C1 C11 126.71(4) . . . no C2 C1 C11 130.54(6) . . . no C4 C1 C5 87.61(5) . . . no C2 C1 C4 87.63(5) . . . no C5 C1 C11 123.36(6) . . . no C1 C2 C3 73.49(4) . . . no N1 C3 C4 123.11(5) . . . yes C2 C3 C5 87.63(5) . . . no N1 C3 C5 128.00(6) . . . yes C2 C3 C4 87.82(5) . . . no N1 C3 C2 129.28(5) . . . yes C4 C3 C5 87.81(4) . . . no C1 C4 C3 74.00(4) . . . no C1 C5 C3 73.81(4) . . . no O3 C6 N1 112.41(6) . . . yes O3 C6 O4 124.70(6) . . . yes O4 C6 N1 122.89(6) . . . yes O3 C7 C8 101.78(4) . . . yes O3 C7 C9 110.64(5) . . . yes C9 C7 C10 112.69(6) . . . no O3 C7 C10 110.08(4) . . . yes C8 C7 C9 110.32(5) . . . no C8 C7 C10 110.82(6) . . . no O1 C11 O2 124.02(8) . . . yes O1 C11 C1 111.85(7) . . . yes O2 C11 C1 124.12(5) . . . yes C1 C2 H21 116.56 . . . no C1 C2 H22 115.54 . . . no C3 C2 H21 117.01 . . . no C3 C2 H22 115.40 . . . no H21 C2 H22 113.32 . . . no C1 C4 H41 114.28 . . . no C1 C4 H42 117.03 . . . no C3 C4 H41 114.54 . . . no C3 C4 H42 114.22 . . . no H41 C4 H42 116.02 . . . no C1 C5 H51 115.56 . . . no C1 C5 H52 115.24 . . . no C3 C5 H51 115.21 . . . no C3 C5 H52 115.29 . . . no H51 C5 H52 115.31 . . . no C7 C8 H81 110.44 . . . no C7 C8 H82 108.76 . . . no C7 C8 H83 108.86 . . . no H81 C8 H82 109.47 . . . no H81 C8 H83 109.90 . . . no H82 C8 H83 109.38 . . . no C7 C9 H91 113.38 . . . no C7 C9 H92 109.46 . . . no C7 C9 H93 111.60 . . . no H91 C9 H92 106.86 . . . no H91 C9 H93 107.95 . . . no H92 C9 H93 107.30 . . . no C7 C10 H101 110.22 . . . no C7 C10 H102 107.23 . . . no C7 C10 H103 110.97 . . . no H101 C10 H102 110.05 . . . no H101 C10 H103 107.99 . . . no H102 C10 H103 110.39 . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O3 C6 O4 2.72(10) . . . . no C7 O3 C6 N1 -177.76(5) . . . . no C6 O3 C7 C8 -179.03(5) . . . . no C6 O3 C7 C9 -61.80(7) . . . . no C6 O3 C7 C10 63.41(7) . . . . no C6 N1 C3 C5 58.60(9) . . . . no C3 N1 C6 O3 5.74(9) . . . . no C6 N1 C3 C4 175.44(6) . . . . no C6 N1 C3 C2 -66.23(10) . . . . no C3 N1 C6 O4 -174.72(8) . . . . no C5 C1 C2 C3 -44.02(4) . . . . no C11 C1 C5 C3 -177.12(5) . . . . no C11 C1 C2 C3 -177.56(6) . . . . no C2 C1 C4 C3 -43.98(4) . . . . no C5 C1 C4 C3 43.75(4) . . . . no C11 C1 C4 C3 174.70(7) . . . . no C2 C1 C5 C3 44.14(4) . . . . no C4 C1 C5 C3 -43.59(4) . . . . no C4 C1 C2 C3 43.69(4) . . . . no C4 C1 C11 O1 -11.54(10) . . . . no C2 C1 C11 O1 -136.28(8) . . . . no C2 C1 C11 O2 44.96(11) . . . . no C5 C1 C11 O2 -74.92(9) . . . . no C4 C1 C11 O2 169.70(7) . . . . no C5 C1 C11 O1 103.84(8) . . . . no C1 C2 C3 C4 -43.88(4) . . . . no C1 C2 C3 N1 -176.34(6) . . . . no C1 C2 C3 C5 44.01(4) . . . . no N1 C3 C4 C1 -179.02(7) . . . . no C2 C3 C4 C1 43.96(4) . . . . no C5 C3 C4 C1 -43.74(4) . . . . no N1 C3 C5 C1 175.36(5) . . . . no C2 C3 C5 C1 -44.13(3) . . . . no C4 C3 C5 C1 43.78(4) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 O4 2.5924(14) . 2_665 no O2 N1 3.0901(10) . 2_665 no O2 C5 3.3896(10) . 2_565 no O3 C5 3.1422(7) . . no O3 C2 3.1826(7) . . no O4 C10 3.0473(11) . . no O4 C11 3.4193(9) . 2_464 no O4 C9 2.9887(9) . . no O4 O1 2.5924(14) . 2_464 no O1 H91 2.8617 . 3_555 no O1 H103 2.6883 . 2_565 no O2 H92 2.7288 . 4_555 no O2 H42 2.8845 . 1_655 no O2 H1 2.0765 . 2_665 no O2 H51 2.4171 . 2_565 no O2 H22 2.7307 . 1_655 no O3 H52 2.8047 . . no O3 H21 2.8741 . . no O4 H101 2.4365 . . no O4 H93 2.4156 . . no O4 H10 1.6543 . 2_464 no O4 H83 2.7813 . 4_454 no N1 O2 3.0901(10) . 2_464 no N1 H10 2.9459 . 2_464 no C2 O3 3.1826(7) . . no C5 C11 3.5093(9) . 2_564 no C5 O3 3.1422(7) . . no C5 O2 3.3896(10) . 2_564 no C9 O4 2.9887(9) . . no C10 O4 3.0473(11) . . no C11 C5 3.5093(9) . 2_565 no C11 O4 3.4193(9) . 2_665 no C4 H82 2.9576 . 3_455 no C6 H93 2.8854 . . no C6 H101 2.8255 . . no C6 H10 2.5803 . 2_464 no C8 H101 2.9834 . 4_555 no C9 H81 3.0810 . 1_455 no C9 H41 2.9214 . 3_445 no C9 H21 3.0968 . 4_454 no C11 H1 2.8741 . 2_665 no C11 H51 2.6571 . 2_565 no H1 O2 2.0765 . 2_464 no H1 C11 2.8741 . 2_464 no H1 H10 2.4734 . 2_464 no H10 O4 1.6543 . 2_665 no H10 N1 2.9459 . 2_665 no H10 C6 2.5803 . 2_665 no H10 H1 2.4734 . 2_665 no H21 O3 2.8741 . . no H21 H52 2.2765 . . no H21 C9 3.0968 . 4_555 no H21 H93 2.4501 . 4_555 no H22 O2 2.7307 . 1_455 no H22 H42 2.2581 . . no H41 H51 2.2254 . . no H41 C9 2.9214 . 3_555 no H41 H82 2.3399 . 3_455 no H41 H91 2.5492 . 3_555 no H41 H92 2.5508 . 3_555 no H42 O2 2.8845 . 1_455 no H42 H22 2.2581 . . no H51 H41 2.2254 . . no H51 O2 2.4171 . 2_564 no H51 C11 2.6571 . 2_564 no H51 H92 2.5712 . 3_555 no H52 O3 2.8047 . . no H52 H21 2.2765 . . no H81 C9 3.0810 . 1_655 no H81 H93 2.5153 . 1_655 no H81 H103 2.5329 . . no H82 H92 2.5318 . . no H82 H102 2.5120 . . no H82 C4 2.9576 . 3_545 no H82 H41 2.3399 . 3_545 no H83 H91 2.5134 . . no H83 O4 2.7813 . 4_555 no H83 H101 2.3884 . 4_555 no H91 H83 2.5134 . . no H91 O1 2.8617 . 3_445 no H91 H41 2.5492 . 3_445 no H92 H82 2.5318 . . no H92 H102 2.5862 . . no H92 H41 2.5508 . 3_445 no H92 H51 2.5712 . 3_445 no H92 O2 2.7288 . 4_454 no H93 O4 2.4156 . . no H93 C6 2.8854 . . no H93 H81 2.5153 . 1_455 no H93 H101 2.5577 . . no H93 H21 2.4501 . 4_454 no H101 O4 2.4365 . . no H101 C6 2.8255 . . no H101 H93 2.5577 . . no H101 C8 2.9834 . 4_454 no H101 H83 2.3884 . 4_454 no H102 H82 2.5120 . . no H102 H92 2.5862 . . no H103 H81 2.5329 . . no H103 O1 2.6883 . 2_564 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N1 H1 O2 1.0407 2.0765 3.0901(10) 163.96 2_464 yes O1 H10 O4 0.9512 1.6543 2.5924(14) 168.07 2_665 yes C5 H51 O2 1.0914 2.4171 3.3896(10) 147.62 2_564 yes C9 H93 O4 1.0899 2.4156 2.9887(9) 111.26 . yes C10 H101 O4 1.0912 2.4365 3.0473(11) 113.96 . yes loop_ _publ_manuscript_incl_extra_item '_geom_extra_tableA_col_1' '_geom_extra_tableA_col_2' '_geom_extra_tableA_col_3' '_geom_extra_tableA_col_4' '_geom_extra_tableA_col_5' '_geom_extra_table_head_A' _geom_extra_table_head_A ; Summary of topological data at the bond critical points (BCP, located at r~b~ where nabla \r(r~b~)=0). The quantities given are \r(r~b~) and nabla^2^ \r(r~b~)) and the ellipticity \e (defined by \e= \l~1~/\l~2~^-1^, with \l~1~, \l~2~ being the two principal curvatures of \r(r) at a BCP), a measure for the charge asphericity. First row experimental results after multipole refinement, second an third subsequent rows: single point ab initio calculations at the experimental geometry, fourth and fifth row: single point ab initio calculations after geometry optimization at the HF/6-311+G(d,p) level. Bond length are experimental (first row) and optimized theoretically (second row). ; loop_ _geom_extra_tableA_col_1 _geom_extra_tableA_col_2 _geom_extra_tableA_col_3 _geom_extra_tableA_col_4 _geom_extra_tableA_col_5 bond/bond length[\%A] \r[e\%A^-3^] nabla^2^\r[e\%A^-5^] ellipticity method C(1)--C(2) 1.60(2) -10.66(8) 0.10 multipole 1.5612(7) 1.59 -13.2 0.02 HF/6-311+G(d,p)(exp. geo.) 1.5386 1.52 -10.4 0.02 B3LYP/6-311+G(d,p)(exp. geo.) 1.67 -14.8 0.02 HF/6-311+G(d,p)(opt. geo.) 1.54 -11.8 0.02 B3LYP/6-311+G(d,p)(opt. geo.) C(1)--C(4) 1.53(3) -9.69(9) 0.15 multipole 1.5548(7) 1.62 -13.9 0.02 HF/6-311+G(d,p)(exp. geo.) 1.5472 1.55 -10.9 0.02 B3LYP/6-311+G(d,p)(exp. geo.) 1.63 -14.0 0.02 HF/6-311+G(d,p)(opt. geo.) 1.56 -11.0 0.02 B3LYP/6-311+G(d,p)(opt. geo.) C(1)--C(5) 1.59(3) -11.39(8) 0.09 multipole 1.5553(6) 1.60 -13.5 0.03 HF/6-311+G(d,p)(exp. geo.) 1.5510 1.53 -10.6 0.02 B3LYP/6-311+G(d,p)(exp. geo.) 1.61 -13.6 0.03 HF/6-311+G(d,p)(opt. geo.) 1.54 -10.7 0.03 B3LYP/6-311+G(d,p)(opt. geo.) C(3)--C(2) 1.65(2) -13.07(7) 0.15 multipole 1.5613(6) 1.63 -14.0 0.02 HF/6-311+G(d,p)(exp. geo.) 1.5476 1.54 -10.9 0.02 B3LYP/6-311+G(d,p)(exp. geo.) 1.67 -14.7 0.02 HF/6-311+G(d,p)(opt. geo.) 1.59 -11.5 0.01 B3LYP/6-311+G(d,p)(opt. geo.) C(3)--C(4) 1.63(3) -12.63(9) 0.08 multipole 1.5493(7) 1.66 -14.6 0.00 HF/6-311+G(d,p)(exp. geo.) 1.5409 1.58 -11.5 0.00 B3LYP/6-311+G(d,p)(exp. geo.) 1.69 -15.1 0.01 HF/6-311+G(d,p)(opt. geo.) 1.60 -11.9 0.00 B3LYP/6-311+G(d,p)(opt. geo.) C(3)--C(5) 1.67(3) -13.07(7) 0.10 multipole 1.5554(7) 1.65 -14.3 0.02 HF/6-311+G(d,p)(exp. geo.) 1.5475 1.56 -11.2 0.02 B3LYP/6-311+G(d,p)(exp. geo.) 1.67 -14.7 0.02 HF/6-311+G(d,p)(opt. geo.) 1.59 -11.5 0.01 B3LYP/6-311+G(d,p)(opt. geo.) C(1)--C(11) 1.94(3) -21.3(10) 0.03 multipole 1.4949(6) 1.88 -20.6 0.07 HF/6-311+G(d,p)(exp. geo.) 1.4913 1.79 -16.2 0.07 B3LYP/6-311+G(d,p)(exp. geo.) 1.90 -20.8 0.07 HF/6-311+G(d,p)(opt. geo.) 1.80 -16.5 0.07 B3LYP/6-311+G(d,p)(opt. geo.) C(11)--O(1) 2.49(4) -32.5(3) 0.23 multipole 1.3257(8) 2.10 -2.2 0.14 HF/6-311+G(d,p)(exp. geo.) 1.3295 2.10 -9.0 0.03 B3LYP/6-311+G(d,p)(exp. geo.) 2.08 -2.2 0.14 HF/6-311+G(d,p)(opt. geo.) 2.09 -9.3 0.03 B3LYP/6-311+G(d,p)(opt. geo.) C(11)--O(2) 3.09(5) -36.1(4) 0.10 multipole 1.2274(7) 2.75 -5.8 0.07 HF/6-311+G(d,p)(exp. geo.) 1.1826 2.72 -9.9 0.09 B3LYP/6-311+G(d,p)(exp. geo.) 2.99 +3.5 0.08 HF/6-311+G(d,p)(opt. geo.) 2.98 -1.9 0.08 B3LYP/6-311+G(d,p)(opt. geo.) N(1)--C(3) 1.99(4) -27.3(2) 0.09 multipole 1.4331(6) 1.83 -15.1 0.03 HF/6-311+G(d,p)(exp. geo.) 1.4219 1.83 -17.8 0.06 B3LYP/6-311+G(d,p)(exp. geo.) 1.87 -15.2 0.04 HF/6-311+G(d,p)(opt. geo.) 1.87 -18.5 0.06 B3LYP/6-311+G(d,p)(opt. geo.) N(1)--C(6) 2.52(4) -26.7(2) 0.26 multipole 1.3579(6) 2.26 -26.0 0.11 HF/6-311+G(d,p)(exp. geo.) 1.3577 2.21 -24.4 0.19 B3LYP/6-311+G(d,p)(exp. geo.) 2.25 -25.1 0.10 HF/6-311+G(d,p)(opt. geo.) 2.21 -24.1 0.19 B3LYP/6-311+G(d,p)(opt. geo.) C(6)--O(3) 2.60(4) -33.4(2) 0.02 multipole 1.3294(6) 2.13 -7.4 0.05 HF/6-311+G(d,p)(exp. geo.) 1.3180 2.12 -12.4 0.05 B3LYP/6-311+G(d,p)(exp. geo.) 2.16 -5.1 0.05 HF/6-311+G(d,p)(opt. geo.) 2.16 -10.8 0.04 B3LYP/6-311+G(d,p)(opt. geo.) C(6)--O(4) 3.11(5) -42.0(3) 0.05 multipole 1.2406(7) 2.72 -12.5 0.07 HF/6-311+G(d,p)(exp. geo.) 1.1922 2.68 -14.7 0.11 B3LYP/6-311+G(d,p)(exp. geo.) 2.97 -3.1 0.08 HF/6-311+G(d,p)(opt. geo.) 2.94 -6.8 0.10 B3LYP/6-311+G(d,p)(opt. geo.) O(3)--C(7) 1.81(4) -19.4(2) 0.01 multipole 1.4845(7) 1.36 +1.5 0.05 HF/6-311+G(d,p)(exp. geo.) 1.4528 1.43 -7.2 0.01 B3LYP/6-311+G(d,p)(exp. geo.) 1.45 +3.4 0.02 HF/6-311+G(d,p)(opt. geo.) 1.52 -6.8 0.00 B3LYP/6-311+G(d,p)(opt. geo.) C(7)--C(8) 1.89(2) -20.02(6) 0.08 multipole 1.5215(7) 1.79 -18.0 0.04 HF/6-311+G(d,p)(exp. geo.) 1.5252 1.70 -14.5 0.03 B3LYP/6-311+G(d,p)(exp. geo.) 1.78 -17.8 0.04 HF/6-311+G(d,p)(opt. geo.) 1.69 -14.3 0.04 B3LYP/6-311+G(d,p)(opt. geo.) C(7)--C(9) 1.86(2) -18.87(7) 0.07 multipole 1.5220(7) 1.78 -17.7 0.03 HF/6-311+G(d,p)(exp. geo.) 1.5269 1.69 -14.2 0.03 B3LYP/6-311+G(d,p)(exp. geo.) 1.76 -17.4 0.03 HF/6-311+G(d,p)(opt. geo.) 1.67 -13.9 0.03 B3LYP/6-311+G(d,p)(opt. geo.) C(7)--C(10) 1.86(2) -18.85(7) 0.07 multipole 1.5242(8) 1.77 -17.6 0.03 HF/6-311+G(d,p)(exp. geo.) 1.5269 1.68 -14.0 0.03 B3LYP/6-311+G(d,p)(exp. geo.) 1.76 -17.4 0.03 HF/6-311+G(d,p)(opt. geo.) 1.67 -13.9 0.03 B3LYP/6-311+G(d,p)(opt. geo.) C(1)--C(3) 0.68(2) 11.09(6) -- multipole 1.8680(6) 0.66 11.85 -- HF/6-311+G(d,p)(exp. geo.) 1.8538 0.67 11.09 -- B3LYP/6-311+G(d,p)(exp. geo.) 0.68 12.21 -- HF/6-311+G(d,p)(opt. geo.) 0.69 11.42 -- B3LYP/6-311+G(d,p)(opt. geo.) # End of Crystallographic Information File