Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_General _database_code_CSD 166281 _audit_creation_date 'Thu Apr 26 16:26:02 2001' _audit_creation_method 'by teXsan' _audit_update_record ? #--------------------------------------------------------------------------- # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #--------------------------------------------------------------------------- # SUBMISSION DETAILS _publ_contact_author_name ' Dr Mitsutoshi Masuda' _publ_contact_author_address ; Nanoarchitectonics Research Center National Institute of Advanced Industrial Science and Technology Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan ; _publ_contact_author_email ' m-masuda@aist.go.jp ' _publ_contact_author_fax ' +81-298-61-4545 ' _publ_contact_author_phone ' +81-298-61-4615 ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal ' Chemical Communication' _journal_coden_Cambridge 182 _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #--------------------------------------------------------------------------- # TITLE AND AUTHOR LIST _publ_section_title ; Multilayer structure of unsymmetrical monolayer lipid membrane with "head-to-tail" interface ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name _publ_author_address ' Mitsutoshi Masuda' ; Nanoarchitectonics Research Center National Institute of Advanced Industrial Science and Technology Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan ; 'Toshimi Shimizu ' ; Nanoarchitectonics Research Center National Institute of Advanced Industrial Science and Technology Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan ; _publ_section_synopsis ; ENTER SYNOPSIS ; #--------------------------------------------------------------------- # TEXT _publ_section_abstract ; A synthetic unsymmetrical 1-galactosamide bolaamphiphile self-assembles in methanol to form a multilayer structure comprising unsymmetrical monolayer lipid membranes linked via a sugar/carboxylic acid hydrogen bonding interface. ; _publ_section_comment ; ENTER TEXT ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (2000). teXsan. Single Crystal Structure Analysis Software. Version 1.11. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; The structure was solved by direct method and expanded using Fourier techniques. The non-hydrogen atoms were refined anisotropically. Hydrogen atoms were included and refined. ; #----------------------------------------------------------------------- #----------------------------------------------------------------------- # CHEMICAL DATA _chemical_formula_sum 'C22 H44 N O8 ' _chemical_formula_moiety 'C22 H44 N O8 ' _chemical_formula_weight 450.59 _chemical_melting_point ? #-------------------------------------------------------------------------- # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-z _cell_length_a 4.905(1) _cell_length_b 40.139(1) _cell_length_c 6.289(1) _cell_angle_alpha 90 _cell_angle_beta 106.48(1) _cell_angle_gamma 90 _cell_volume 1187.3(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 20 _cell_measurement_theta_min 19.39 _cell_measurement_theta_max 27.56 _cell_measurement_temperature 273.2 #-------------------------------------------------------------------------- _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.779 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 1.000 #--------------------------------------------------------------------------- # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 2038 _diffrn_reflns_av_R_equivalents 0.014 _diffrn_reflns_theta_max 59.96 _diffrn_measured_fraction_theta_max 0.5526 _diffrn_reflns_theta_full 59.96 _diffrn_measured_fraction_theta_full 0.5526 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.15 #-------------------------------------------------------------------------- # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 2.9 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 646 _reflns_number_gt 1900 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0470 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 1929 _refine_ls_number_parameters 445 _refine_ls_goodness_of_fit_ref 1.270 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00126|Fo|^2^]' _refine_ls_shift/su_max 0.0657 _refine_diff_density_max 0.22 _refine_diff_density_min -0.17 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.09(1) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack -0.6(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'O' 'O' 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'N' 'N' 0.031 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #----------------------------------------------------------------------- # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(2) O 0.2004(3) 0.53717(4) -1.5622(2) 0.0435(3) Uani 1.00 d . . . O(3) O -0.0143(3) 0.59983(4) -1.7805(2) 0.0420(3) Uani 1.00 d . . . O(4) O -0.1122(3) 0.63190(4) -1.4298(2) 0.0444(4) Uani 1.00 d . . . O(5) O 0.3056(2) 0.59418(4) -1.0986(2) 0.0334(3) Uani 1.00 d . . . O(6) O 0.5647(5) 0.65608(5) -0.8548(3) 0.0739(5) Uani 1.00 d . . . O(7) O 0.7768(3) 0.5228 -0.9790(2) 0.0444(3) Uani 1.00 d . . . O(8) O 1.1826(6) 0.19853(6) 1.3692(4) 0.1017(7) Uani 1.00 d . . . O(9) O 1.5421(5) 0.21005(6) 1.6517(3) 0.0838(6) Uani 1.00 d . . . N(1) N 0.3122(3) 0.53649(4) -1.0950(2) 0.0332(3) Uani 1.00 d . . . C(1) C 0.3505(3) 0.56529(5) -1.2185(3) 0.0296(4) Uani 1.00 d . . . C(2) C 0.1447(4) 0.56589(5) -1.4507(3) 0.0314(4) Uani 1.00 d . . . C(3) C 0.1916(3) 0.59745(5) -1.5699(3) 0.0319(4) Uani 1.00 d . . . C(4) C 0.1753(4) 0.62818(5) -1.4331(3) 0.0340(4) Uani 1.00 d . . . C(5) C 0.3733(4) 0.62429(5) -1.1976(3) 0.0332(4) Uani 1.00 d . . . C(6) C 0.3443(5) 0.65337(5) -1.0533(3) 0.0430(5) Uani 1.00 d . . . C(7) C 0.5282(3) 0.51709(5) -0.9855(3) 0.0318(4) Uani 1.00 d . . . C(8) C 0.4495(4) 0.48655(5) -0.8731(3) 0.0363(4) Uani 1.00 d . . . C(9) C 0.6591(4) 0.47941(5) -0.6486(3) 0.0397(5) Uani 1.00 d . . . C(10) C 0.5783(5) 0.44882(6) -0.5375(3) 0.0446(5) Uani 1.00 d . . . C(11) C 0.7919(4) 0.44092(6) -0.3173(3) 0.0437(5) Uani 1.00 d . . . C(12) C 0.7170(5) 0.40979(6) -0.2049(4) 0.0467(5) Uani 1.00 d . . . C(13) C 0.9289(5) 0.40152(6) 0.0158(4) 0.0470(5) Uani 1.00 d . . . C(14) C 0.8539(5) 0.37049(6) 0.1260(4) 0.0484(5) Uani 1.00 d . . . C(15) C 1.0664(5) 0.36230(6) 0.3475(4) 0.0488(5) Uani 1.00 d . . . C(16) C 0.9914(5) 0.33125(7) 0.4568(4) 0.0498(5) Uani 1.00 d . . . C(17) C 1.2039(5) 0.32291(6) 0.6772(4) 0.0518(6) Uani 1.00 d . . . C(18) C 1.1274(5) 0.29194(6) 0.7878(4) 0.0505(6) Uani 1.00 d . . . C(19) C 1.3405(5) 0.28335(6) 1.0072(4) 0.0538(6) Uani 1.00 d . . . C(20) C 1.2584(5) 0.25294(6) 1.1185(4) 0.0526(6) Uani 1.00 d . . . C(21) C 1.4633(5) 0.24514(7) 1.3413(4) 0.0549(6) Uani 1.00 d . . . C(22) C 1.3791(5) 0.21582(6) 1.4542(4) 0.0494(5) Uani 1.00 d . . . H(1c) H 0.541(3) 0.5637(4) -1.229(2) 0.013(4) Uiso 1.00 calc . . . H(1n) H 0.106(2) 0.5289(6) -1.105(4) 0.054(6) Uiso 1.00 calc . . . H(2c) H -0.055(5) 0.5663(5) -1.448(3) 0.035(5) Uiso 1.00 calc . . . H(2o) H 0.053(4) 0.5382(7) -1.702(3) 0.065(7) Uiso 1.00 calc . . . H(3c) H 0.368(4) 0.5956(4) -1.591(3) 0.019(4) Uiso 1.00 calc . . . H(3o) H 0.089(5) 0.5978(8) -1.890(4) 0.074(8) Uiso 1.00 calc . . . H(4c) H 0.226(4) 0.6484(5) -1.505(3) 0.025(4) Uiso 1.00 calc . . . H(4o) H -0.122(7) 0.6560(2) -1.421(5) 0.078(9) Uiso 1.00 calc . . . H(5c) H 0.556(4) 0.6233(4) -1.202(3) 0.018(4) Uiso 1.00 calc . . . H(6cb) H 0.333(5) 0.6752(6) -1.124(4) 0.042(5) Uiso 1.00 calc . . . H(6ca) H 0.164(5) 0.6517(6) -1.015(4) 0.039(5) Uiso 1.00 calc . . . H(6o) H 0.660(7) 0.6354(5) -0.801(6) 0.09(1) Uiso 1.00 calc . . . H(8ca) H 0.455(4) 0.4683(6) -0.968(3) 0.037(5) Uiso 1.00 calc . . . H(8cb) H 0.250(5) 0.4886(6) -0.859(4) 0.049(6) Uiso 1.00 calc . . . H(9cb) H 0.656(5) 0.4991(7) -0.556(4) 0.050(6) Uiso 1.00 calc . . . H(9ca) H 0.852(6) 0.4765(6) -0.658(4) 0.049(6) Uiso 1.00 calc . . . H(9o) H 1.506(7) 0.1890(4) 1.714(5) 0.075(9) Uiso 1.00 calc . . . H(10cb) H 0.385(6) 0.4524(7) -0.518(4) 0.058(7) Uiso 1.00 calc . . . H(10ca) H 0.577(6) 0.4297(7) -0.630(5) 0.060(7) Uiso 1.00 calc . . . H(11cb) H 0.811(6) 0.4596(6) -0.214(4) 0.052(6) Uiso 1.00 calc . . . H(11ca) H 0.981(6) 0.4362(7) -0.331(4) 0.057(7) Uiso 1.00 calc . . . H(12cb) H 0.535(8) 0.4125(10) -0.195(6) 0.09(1) Uiso 1.00 calc . . . H(12ca) H 0.704(5) 0.3913(6) -0.305(4) 0.046(6) Uiso 1.00 calc . . . H(13cb) H 0.946(6) 0.4211(8) 0.118(5) 0.066(8) Uiso 1.00 calc . . . H(13ca) H 1.113(6) 0.3990(7) -0.007(4) 0.058(7) Uiso 1.00 calc . . . H(14cb) H 0.671(7) 0.3740(7) 0.149(5) 0.063(7) Uiso 1.00 calc . . . H(14ca) H 0.861(5) 0.3522(6) 0.026(4) 0.042(6) Uiso 1.00 calc . . . H(15cb) H 1.074(7) 0.3809(9) 0.446(5) 0.074(8) Uiso 1.00 calc . . . H(15ca) H 1.253(6) 0.3591(6) 0.325(4) 0.052(6) Uiso 1.00 calc . . . H(16cb) H 0.815(6) 0.3350(7) 0.488(4) 0.061(7) Uiso 1.00 calc . . . H(16ca) H 0.997(6) 0.3136(8) 0.355(5) 0.068(8) Uiso 1.00 calc . . . H(17cb) H 1.235(5) 0.3433(7) 0.785(4) 0.054(6) Uiso 1.00 calc . . . H(17ca) H 1.394(7) 0.3187(7) 0.656(5) 0.068(8) Uiso 1.00 calc . . . H(18cb) H 0.969(8) 0.2953(9) 0.823(6) 0.09(1) Uiso 1.00 calc . . . H(18ca) H 1.106(8) 0.2741(10) 0.692(6) 0.09(1) Uiso 1.00 calc . . . H(19cb) H 1.390(6) 0.3019(8) 1.107(4) 0.060(7) Uiso 1.00 calc . . . H(19ca) H 1.532(7) 0.2780(8) 0.981(5) 0.077(9) Uiso 1.00 calc . . . H(20cb) H 1.079(7) 0.2557(8) 1.144(5) 0.072(8) Uiso 1.00 calc . . . H(20ca) H 1.255(7) 0.2346(9) 1.023(5) 0.072(8) Uiso 1.00 calc . . . H(21cb) H 1.487(6) 0.2648(7) 1.433(4) 0.061(7) Uiso 1.00 calc . . . H(21ca) H 1.637(7) 0.2377(8) 1.322(5) 0.073(8) Uiso 1.00 calc . . . 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 O(2) 0.0534(7) 0.0366(6) 0.0366(6) 0.0072(6) 0.0066(5) -0.0070(5) O(3) 0.0464(7) 0.0502(7) 0.0256(5) 0.0032(6) 0.0041(5) 0.0005(5) O(4) 0.0388(6) 0.0458(7) 0.0477(8) 0.0093(6) 0.0105(6) -0.0036(6) O(5) 0.0416(6) 0.0330(6) 0.0268(5) 0.0034(5) 0.0116(4) 0.0016(5) O(6) 0.092(1) 0.0609(10) 0.0436(8) 0.0231(9) -0.0211(8) -0.0198(7) O(7) 0.0302(5) 0.0525(7) 0.0507(7) 0.0022(6) 0.0117(5) 0.0160(6) O(8) 0.113(2) 0.079(1) 0.079(1) -0.056(1) -0.029(1) 0.0386(10) O(9) 0.105(1) 0.073(1) 0.0530(9) -0.026(1) -0.0104(9) 0.0282(9) N(1) 0.0299(6) 0.0356(7) 0.0346(7) 0.0025(5) 0.0099(5) 0.0074(6) C(1) 0.0280(8) 0.0305(8) 0.0322(8) 0.0027(7) 0.0118(6) 0.0034(6) C(2) 0.0303(8) 0.0331(8) 0.0311(8) 0.0022(7) 0.0091(6) -0.0025(6) C(3) 0.0310(8) 0.0396(8) 0.0262(7) 0.0034(7) 0.0101(6) 0.0020(6) C(4) 0.0376(8) 0.0329(8) 0.0313(8) -0.0012(7) 0.0096(7) 0.0026(7) C(5) 0.0359(9) 0.0324(8) 0.0319(8) -0.0011(7) 0.0108(6) 0.0008(6) C(6) 0.055(1) 0.0349(9) 0.0358(9) 0.0032(9) 0.0080(7) -0.0018(7) C(7) 0.0307(7) 0.0330(8) 0.0314(8) -0.0003(6) 0.0082(6) 0.0002(6) C(8) 0.0357(8) 0.0343(9) 0.0391(9) 0.0015(7) 0.0111(7) 0.0044(8) C(9) 0.0374(9) 0.0385(9) 0.0414(9) -0.0003(8) 0.0081(7) 0.0078(8) C(10) 0.0429(10) 0.0444(10) 0.0451(10) -0.0004(9) 0.0102(7) 0.0148(9) C(11) 0.040(1) 0.044(1) 0.0459(10) -0.0017(8) 0.0099(8) 0.0099(8) C(12) 0.045(1) 0.044(1) 0.048(1) -0.0017(9) 0.0095(8) 0.0115(9) C(13) 0.046(1) 0.046(1) 0.047(1) -0.0010(9) 0.0100(8) 0.0102(9) C(14) 0.048(1) 0.049(1) 0.047(1) -0.0003(9) 0.0118(8) 0.0123(9) C(15) 0.049(1) 0.046(1) 0.049(1) -0.0011(9) 0.0092(8) 0.0117(9) C(16) 0.051(1) 0.050(1) 0.047(1) -0.0006(9) 0.0108(8) 0.0149(9) C(17) 0.049(1) 0.052(1) 0.052(1) -0.0045(9) 0.0092(9) 0.0179(9) C(18) 0.050(1) 0.050(1) 0.050(1) -0.0009(10) 0.0101(9) 0.0158(10) C(19) 0.052(1) 0.052(1) 0.053(1) -0.0046(10) 0.0079(9) 0.0193(10) C(20) 0.055(1) 0.048(1) 0.050(1) -0.0045(10) 0.0078(9) 0.0143(10) C(21) 0.059(1) 0.047(1) 0.053(1) -0.0081(10) 0.0073(10) 0.0143(9) C(22) 0.059(1) 0.0406(10) 0.0462(10) 0.0047(8) 0.0118(8) 0.0076(8) #--------------------------------------------------------------------------- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SHELXS97 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #--------------------------------------------------------------------------- _geom_special_details ; ? ; 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 O(2) C(2) 1.416(3) . . yes O(3) C(3) 1.423(2) . . yes O(4) C(4) 1.424(2) . . yes O(5) C(1) 1.434(2) . . yes O(5) C(5) 1.441(2) . . yes O(6) C(6) 1.405(3) . . yes O(7) C(7) 1.230(3) . . yes O(8) C(22) 1.185(3) . . yes O(9) C(22) 1.293(3) . . yes N(1) C(1) 1.434(2) . . yes N(1) C(7) 1.337(3) . . yes C(1) C(2) 1.522(3) . . yes C(2) C(3) 1.522(3) . . yes C(3) C(4) 1.518(3) . . yes C(4) C(5) 1.531(3) . . yes C(5) C(6) 1.509(3) . . yes C(7) C(8) 1.518(3) . . yes C(8) C(9) 1.520(3) . . yes C(9) C(10) 1.520(3) . . yes C(10) C(11) 1.514(3) . . yes C(11) C(12) 1.531(3) . . yes C(12) C(13) 1.516(3) . . yes C(13) C(14) 1.520(3) . . yes C(14) C(15) 1.520(3) . . yes C(15) C(16) 1.519(3) . . yes C(16) C(17) 1.516(3) . . yes C(17) C(18) 1.522(3) . . yes C(18) C(19) 1.516(3) . . yes C(19) C(20) 1.517(3) . . yes C(20) C(21) 1.507(4) . . yes C(21) C(22) 1.492(3) . . yes #-------------------------------------------------------------------------- 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 C(1) O(5) C(5) 111.2(1) . . . yes C(1) N(1) C(7) 122.8(2) . . . yes O(5) C(1) N(1) 107.7(1) . . . yes O(5) C(1) C(2) 109.4(1) . . . yes N(1) C(1) C(2) 112.3(1) . . . yes O(2) C(2) C(1) 107.1(1) . . . yes O(2) C(2) C(3) 110.9(1) . . . yes C(1) C(2) C(3) 109.5(1) . . . yes O(3) C(3) C(2) 110.4(2) . . . yes O(3) C(3) C(4) 109.6(2) . . . yes C(2) C(3) C(4) 111.0(1) . . . yes O(4) C(4) C(3) 107.8(2) . . . yes O(4) C(4) C(5) 110.8(2) . . . yes C(3) C(4) C(5) 110.1(2) . . . yes O(5) C(5) C(4) 110.0(1) . . . yes O(5) C(5) C(6) 108.4(2) . . . yes C(4) C(5) C(6) 111.2(2) . . . yes O(6) C(6) C(5) 114.5(2) . . . yes O(7) C(7) N(1) 122.8(2) . . . yes O(7) C(7) C(8) 121.0(2) . . . yes N(1) C(7) C(8) 116.2(2) . . . yes C(7) C(8) C(9) 113.0(2) . . . yes C(8) C(9) C(10) 112.6(2) . . . yes C(9) C(10) C(11) 112.7(2) . . . yes C(10) C(11) C(12) 113.5(2) . . . yes C(11) C(12) C(13) 114.2(2) . . . yes C(12) C(13) C(14) 113.9(2) . . . yes C(13) C(14) C(15) 113.8(2) . . . yes C(14) C(15) C(16) 113.6(2) . . . yes C(15) C(16) C(17) 113.8(2) . . . yes C(16) C(17) C(18) 113.8(2) . . . yes C(17) C(18) C(19) 113.9(2) . . . yes C(18) C(19) C(20) 113.5(2) . . . yes C(19) C(20) C(21) 113.7(2) . . . yes C(20) C(21) C(22) 113.9(2) . . . yes O(8) C(22) O(9) 122.0(2) . . . yes O(8) C(22) C(21) 123.2(2) . . . yes O(9) C(22) C(21) 114.8(2) . . . yes #------------------------------------------------- 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 O(2) C(2) C(1) O(5) 179.3(1) . . . . yes O(2) C(2) C(1) N(1) -61.2(2) . . . . yes O(2) C(2) C(1) H(1c) 55(1) . . . . no O(2) C(2) C(3) O(3) 66.8(2) . . . . yes O(2) C(2) C(3) C(4) -171.5(1) . . . . yes O(2) C(2) C(3) H(3c) -51(1) . . . . no O(3) C(3) C(2) C(1) -175.2(1) . . . . yes O(3) C(3) C(2) H(2c) -53(1) . . . . no O(3) C(3) C(4) O(4) 53.0(2) . . . . yes O(3) C(3) C(4) C(5) 174.0(1) . . . . yes O(3) C(3) C(4) H(4c) -63(1) . . . . no O(3) C(3) C(4) H(4o) 31(1) . . . . no O(4) C(4) C(3) C(2) -69.1(2) . . . . yes O(4) C(4) C(3) H(3c) 172(1) . . . . no O(4) C(4) C(5) O(5) 63.6(2) . . . . yes O(4) C(4) C(5) C(6) -56.5(2) . . . . yes O(4) C(4) C(5) H(5c) -176(1) . . . . no O(4) C(4) H(4o) O(8) 169(4) . . . 2_655 no O(4) H(4o) C(4) C(3) 42(2) . . . . no O(4) H(4o) C(4) C(5) -100(1) . . . . no O(4) H(4o) C(4) H(4c) 151(2) . . . . no O(5) C(1) N(1) C(7) -108.4(2) . . . . yes O(5) C(1) N(1) H(1n) 78(1) . . . . no O(5) C(1) C(2) C(3) 59.0(2) . . . . yes O(5) C(1) C(2) H(2c) -58(1) . . . . no O(5) C(5) C(4) C(3) -55.6(2) . . . . yes O(5) C(5) C(4) H(4c) -177(1) . . . . no O(5) C(5) C(4) H(4o) 96.4(8) . . . . no O(5) C(5) C(6) O(6) 74.1(2) . . . . yes O(5) C(5) C(6) H(6cb) -163(1) . . . . no O(5) C(5) C(6) H(6ca) -47(1) . . . . no O(6) C(6) C(5) C(4) -164.8(2) . . . . yes O(6) C(6) C(5) H(5c) -44(1) . . . . no O(6) C(6) H(6cb) H(6ca) -113(1) . . . . no O(6) C(6) H(6ca) H(6cb) 111(1) . . . . no O(7) C(7) N(1) C(1) 1.2(3) . . . . yes O(7) C(7) N(1) H(1n) 174(1) . . . . no O(7) C(7) C(8) C(9) 40.6(3) . . . . yes O(7) C(7) C(8) H(8ca) -77(1) . . . . no O(7) C(7) C(8) H(8cb) 165(1) . . . . no O(8) C(22) O(9) H(9o) 8(2) . . . . no O(8) C(22) C(21) C(20) 6.1(5) . . . . yes O(8) C(22) C(21) H(21cb 129(2) . . . . no O(8) C(22) C(21) H(21ca -111(2) . . . . no O(9) C(22) O(8) H(4o) -24(1) . . . 2_645 no O(9) C(22) C(21) C(20) -175.7(3) . . . . yes O(9) C(22) C(21) H(21cb -52(2) . . . . no O(9) C(22) C(21) H(21ca 66(2) . . . . no N(1) C(1) O(5) C(5) 173.1(1) . . . . yes N(1) C(1) C(2) C(3) 178.5(1) . . . . yes N(1) C(1) C(2) H(2c) 60(1) . . . . no N(1) C(7) C(8) C(9) -141.3(2) . . . . yes N(1) C(7) C(8) H(8ca) 100(1) . . . . no N(1) C(7) C(8) H(8cb) -16(1) . . . . no C(1) O(5) C(5) C(4) 62.8(2) . . . . yes C(1) O(5) C(5) C(6) -175.5(2) . . . . yes C(1) O(5) C(5) H(5c) -57(1) . . . . no C(1) N(1) C(7) C(8) -176.9(2) . . . . yes C(1) C(2) O(2) H(2o) 175(1) . . . . no C(1) C(2) C(3) C(4) -53.6(2) . . . . yes C(1) C(2) C(3) H(3c) 66(1) . . . . no C(2) C(1) O(5) C(5) -64.6(2) . . . . yes C(2) C(1) N(1) C(7) 131.1(2) . . . . yes C(2) C(1) N(1) H(1n) -42(1) . . . . no C(2) C(3) O(3) H(3o) -113(2) . . . . no C(2) C(3) C(4) C(5) 51.9(2) . . . . yes C(2) C(3) C(4) H(4c) 174(1) . . . . no C(2) C(3) C(4) H(4o) -90(1) . . . . no C(3) C(2) O(2) H(2o) -65(1) . . . . no C(3) C(2) C(1) H(1c) -65(1) . . . . no C(3) C(4) O(4) H(4o) -148(1) . . . . no C(3) C(4) C(5) C(6) -175.7(2) . . . . yes C(3) C(4) C(5) H(5c) 64(1) . . . . no C(4) C(3) O(3) H(3o) 123(2) . . . . no C(4) C(3) C(2) H(2c) 67(1) . . . . no C(4) C(5) C(6) H(6cb) -42(1) . . . . no C(4) C(5) C(6) H(6ca) 73(1) . . . . no C(5) O(5) C(1) H(1c) 57(1) . . . . no C(5) C(4) O(4) H(4o) 90(1) . . . . no C(5) C(4) C(3) H(3c) -66(1) . . . . no C(5) C(6) O(6) H(6o) -25(2) . . . . no C(5) C(6) O(6) H(9o) -178(1) . . . 2_756 no C(5) C(6) H(6cb) H(6ca) 119(1) . . . . no C(5) C(6) H(6ca) H(6cb) -123(1) . . . . no C(6) C(5) C(4) H(4c) 62(1) . . . . no C(6) C(5) C(4) H(4o) -23.7(8) . . . . no C(7) N(1) C(1) H(1c) 12(1) . . . . no C(7) C(8) C(9) C(10) 179.9(2) . . . . yes C(7) C(8) C(9) H(9cb) 60(1) . . . . no C(7) C(8) C(9) H(9ca) -57(1) . . . . no C(7) C(8) H(8ca) H(8cb) -118(1) . . . . no C(7) C(8) H(8cb) H(8ca) 115(1) . . . . no C(8) C(7) N(1) H(1n) -3(1) . . . . no C(8) C(9) C(10) C(11) 178.0(2) . . . . yes C(8) C(9) C(10) H(10cb -59(1) . . . . no C(8) C(9) C(10) H(10ca 60(2) . . . . no C(8) C(9) H(9cb) H(9ca) -120(1) . . . . no C(8) C(9) H(9ca) H(9cb) 116(1) . . . . no C(9) C(8) H(8ca) H(8cb) 119(1) . . . . no C(9) C(8) H(8cb) H(8ca) -118(1) . . . . no C(9) C(10) C(11) C(12) -178.9(2) . . . . yes C(9) C(10) C(11) H(11cb 59(1) . . . . no C(9) C(10) C(11) H(11ca -60(2) . . . . no C(9) C(10) H(10cb H(10ca 119(2) . . . . no C(9) C(10) H(10ca H(10cb -119(2) . . . . no C(10) C(9) C(8) H(8ca) -63(1) . . . . no C(10) C(9) C(8) H(8cb) 55(1) . . . . no C(10) C(9) H(9cb) H(9ca) 117(1) . . . . no C(10) C(9) H(9ca) H(9cb) -118(1) . . . . no C(10) C(11) C(12) C(13) 180.0(2) . . . . yes C(10) C(11) C(12) H(12cb -53(2) . . . . no C(10) C(11) C(12) H(12ca 58(1) . . . . no C(10) C(11) H(11cb H(11ca -123(2) . . . . no C(10) C(11) H(11ca H(11cb 122(2) . . . . no C(11) C(10) C(9) H(9cb) -64(1) . . . . no C(11) C(10) C(9) H(9ca) 53(1) . . . . no C(11) C(10) H(10cb H(10ca -116(2) . . . . no C(11) C(10) H(10ca H(10cb 119(2) . . . . no C(11) C(12) C(13) C(14) -179.7(2) . . . . yes C(11) C(12) C(13) H(13cb 57(2) . . . . no C(11) C(12) C(13) H(13ca -56(1) . . . . no C(11) C(12) H(12cb H(12ca 114(2) . . . . no C(11) C(12) H(12ca H(12cb -114(2) . . . . no C(12) C(11) C(10) H(10cb 59(1) . . . . no C(12) C(11) C(10) H(10ca -60(1) . . . . no C(12) C(11) H(11cb H(11ca 111(2) . . . . no C(12) C(11) H(11ca H(11cb -114(1) . . . . no C(12) C(13) C(14) C(15) -179.9(2) . . . . yes C(12) C(13) C(14) H(14cb -59(1) . . . . no C(12) C(13) C(14) H(14ca 63(1) . . . . no C(12) C(13) H(13cb H(13ca -116(2) . . . . no C(12) C(13) H(13ca H(13cb 116(2) . . . . no C(13) C(12) C(11) H(11cb -56(1) . . . . no C(13) C(12) C(11) H(11ca 56(1) . . . . no C(13) C(12) H(12cb H(12ca -118(2) . . . . no C(13) C(12) H(12ca H(12cb 121(2) . . . . no C(13) C(14) C(15) C(16) -179.9(2) . . . . yes C(13) C(14) C(15) H(15cb 59(2) . . . . no C(13) C(14) C(15) H(15ca -58(1) . . . . no C(13) C(14) H(14cb H(14ca 116(2) . . . . no C(13) C(14) H(14ca H(14cb -118(2) . . . . no C(14) C(13) C(12) H(12cb 57(2) . . . . no C(14) C(13) C(12) H(12ca -58(1) . . . . no C(14) C(13) H(13cb H(13ca 118(2) . . . . no C(14) C(13) H(13ca H(13cb -117(2) . . . . no C(14) C(15) C(16) C(17) 179.7(2) . . . . yes C(14) C(15) C(16) H(16cb -62(1) . . . . no C(14) C(15) C(16) H(16ca 62(2) . . . . no C(14) C(15) H(15cb H(15ca -118(2) . . . . no C(14) C(15) H(15ca H(15cb 118(2) . . . . no C(15) C(14) C(13) H(13cb -57(2) . . . . no C(15) C(14) C(13) H(13ca 58(1) . . . . no C(15) C(14) H(14cb H(14ca -119(2) . . . . no C(15) C(14) H(14ca H(14cb 120(2) . . . . no C(15) C(16) C(17) C(18) 179.5(2) . . . . yes C(15) C(16) C(17) H(17cb 54(1) . . . . no C(15) C(16) C(17) H(17ca -61(2) . . . . no C(15) C(16) H(16cb H(16ca 117(2) . . . . no C(15) C(16) H(16ca H(16cb -119(2) . . . . no C(16) C(15) C(14) H(14cb 60(1) . . . . no C(16) C(15) C(14) H(14ca -64(1) . . . . no C(16) C(15) H(15cb H(15ca 118(2) . . . . no C(16) C(15) H(15ca H(15cb -117(2) . . . . no C(16) C(17) C(18) C(19) 179.5(2) . . . . yes C(16) C(17) C(18) H(18cb -64(2) . . . . no C(16) C(17) C(18) H(18ca 56(2) . . . . no C(16) C(17) H(17cb H(17ca -118(2) . . . . no C(16) C(17) H(17ca H(17cb 119(1) . . . . no C(17) C(16) C(15) H(15cb -60(2) . . . . no C(17) C(16) C(15) H(15ca 58(1) . . . . no C(17) C(16) H(16cb H(16ca -120(2) . . . . no C(17) C(16) H(16ca H(16cb 119(2) . . . . no C(17) C(18) C(19) C(20) 178.6(2) . . . . yes C(17) C(18) C(19) H(19cb 49(2) . . . . no C(17) C(18) C(19) H(19ca -62(2) . . . . no C(17) C(18) H(18cb H(18ca 120(3) . . . . no C(17) C(18) H(18ca H(18cb -120(3) . . . . no C(18) C(17) C(16) H(16cb 60(2) . . . . no C(18) C(17) C(16) H(16ca -65(2) . . . . no C(18) C(17) H(17cb H(17ca 114(2) . . . . no C(18) C(17) H(17ca H(17cb -117(1) . . . . no C(18) C(19) C(20) C(21) -177.6(3) . . . . yes C(18) C(19) C(20) H(20cb -58(2) . . . . no C(18) C(19) C(20) H(20ca 62(2) . . . . no C(18) C(19) H(19cb H(19ca -116(2) . . . . no C(18) C(19) H(19ca H(19cb 119(2) . . . . no C(19) C(18) C(17) H(17cb -54(1) . . . . no C(19) C(18) C(17) H(17ca 58(1) . . . . no C(19) C(18) H(18cb H(18ca -117(3) . . . . no C(19) C(18) H(18ca H(18cb 113(3) . . . . no C(19) C(20) C(21) C(22) 178.4(2) . . . . yes C(19) C(20) C(21) H(21cb 53(2) . . . . no C(19) C(20) C(21) H(21ca -69(2) . . . . no C(19) C(20) H(20cb H(20ca 118(2) . . . . no C(19) C(20) H(20ca H(20cb -121(2) . . . . no C(20) C(19) C(18) H(18cb 59(2) . . . . no C(20) C(19) C(18) H(18ca -58(2) . . . . no C(20) C(19) H(19cb H(19ca 113(2) . . . . no C(20) C(19) H(19ca H(19cb -117(2) . . . . no C(20) C(21) H(21cb H(21ca -121(2) . . . . no C(20) C(21) H(21ca H(21cb 120(2) . . . . no C(21) C(20) C(19) H(19cb -47(2) . . . . no C(21) C(20) C(19) H(19ca 62(2) . . . . no C(21) C(20) H(20cb H(20ca -117(2) . . . . no C(21) C(20) H(20ca H(20cb 115(2) . . . . no C(21) C(22) O(8) H(4o) 153(1) . . . 2_645 no C(21) C(22) O(9) H(9o) -169(2) . . . . no C(22) C(21) C(20) H(20cb 55(2) . . . . no C(22) C(21) C(20) H(20ca -62(2) . . . . no C(22) C(21) H(21cb H(21ca 112(2) . . . . no C(22) C(21) H(21ca H(21cb -118(2) . . . . no H(1c) C(1) N(1) H(1n) -160(2) . . . . no H(1c) C(1) C(2) H(2c) 176(2) . . . . no H(2c) C(2) O(2) H(2o) 52(2) . . . . no H(2c) C(2) C(3) H(3c) -171(1) . . . . no H(3c) C(3) O(3) H(3o) 2(2) . . . . no H(3c) C(3) C(4) H(4c) 56(1) . . . . no H(3c) C(3) C(4) H(4o) 151(1) . . . . no H(4c) C(4) O(4) H(4o) -29(2) . . . . no H(4c) C(4) C(5) H(5c) -57(1) . . . . no H(4o) C(4) C(5) H(5c) -143(1) . . . . no H(5c) C(5) C(6) H(6cb) 78(2) . . . . no H(5c) C(5) C(6) H(6ca) -165(2) . . . . no H(6cb) C(6) O(6) H(6o) -152(3) . . . . no H(6cb) C(6) O(6) H(9o) 53(2) . . . 2_756 no H(6ca) C(6) O(6) H(6o) 97(3) . . . . no H(6ca) C(6) O(6) H(9o) -56(2) . . . 2_756 no H(8ca) C(8) C(9) H(9cb) 177(2) . . . . no H(8ca) C(8) C(9) H(9ca) 59(2) . . . . no H(8cb) C(8) C(9) H(9cb) -63(2) . . . . no H(8cb) C(8) C(9) H(9ca) 177(2) . . . . no H(9cb) C(9) C(10) H(10cb 58(2) . . . . no H(9cb) C(9) C(10) H(10ca 178(2) . . . . no H(9ca) C(9) C(10) H(10cb 176(2) . . . . no H(9ca) C(9) C(10) H(10ca -63(2) . . . . no H(10cb C(10) C(11) H(11cb -62(2) . . . . no H(10cb C(10) C(11) H(11ca 177(2) . . . . no H(10ca C(10) C(11) H(11cb 178(2) . . . . no H(10ca C(10) C(11) H(11ca 57(2) . . . . no H(11cb C(11) C(12) H(12cb 69(3) . . . . no H(11cb C(11) C(12) H(12ca -178(2) . . . . no H(11ca C(11) C(12) H(12cb -177(3) . . . . no H(11ca C(11) C(12) H(12ca -64(2) . . . . no H(12cb C(12) C(13) H(13cb -65(3) . . . . no H(12cb C(12) C(13) H(13ca 179(3) . . . . no H(12ca C(12) C(13) H(13cb 178(2) . . . . no H(12ca C(12) C(13) H(13ca 63(2) . . . . no H(13cb C(13) C(14) H(14cb 63(2) . . . . no H(13cb C(13) C(14) H(14ca -173(2) . . . . no H(13ca C(13) C(14) H(14cb 178(2) . . . . no H(13ca C(13) C(14) H(14ca -58(2) . . . . no H(14cb C(14) C(15) H(15cb -60(3) . . . . no H(14cb C(14) C(15) H(15ca -179(2) . . . . no H(14ca C(14) C(15) H(15cb 175(2) . . . . no H(14ca C(14) C(15) H(15ca 56(2) . . . . no H(15cb C(15) C(16) H(16cb 57(2) . . . . no H(15cb C(15) C(16) H(16ca -177(2) . . . . no H(15ca C(15) C(16) H(16cb 176(2) . . . . no H(15ca C(15) C(16) H(16ca -58(2) . . . . no H(16cb C(16) C(17) H(17cb -64(2) . . . . no H(16cb C(16) C(17) H(17ca 180.0 . . . . no H(16ca C(16) C(17) H(17cb 169(2) . . . . no H(16ca C(16) C(17) H(17ca 54(2) . . . . no H(17cb C(17) C(18) H(18cb 60(3) . . . . no H(17cb C(17) C(18) H(18ca -178(3) . . . . no H(17ca C(17) C(18) H(18cb 173(3) . . . . no H(17ca C(17) C(18) H(18ca -65(3) . . . . no H(18cb C(18) C(19) H(19cb -70(3) . . . . no H(18cb C(18) C(19) H(19ca 177(3) . . . . no H(18ca C(18) C(19) H(19cb 172(3) . . . . no H(18ca C(18) C(19) H(19ca 60(3) . . . . no H(19cb C(19) C(20) H(20cb 72(3) . . . . no H(19cb C(19) C(20) H(20ca -167(3) . . . . no H(19ca C(19) C(20) H(20cb -178(3) . . . . no H(19ca C(19) C(20) H(20ca -57(3) . . . . no H(20cb C(20) C(21) H(21cb -68(3) . . . . no H(20cb C(20) C(21) H(21ca 168(3) . . . . no H(20ca C(20) C(21) H(21cb 172(3) . . . . no H(20ca C(20) C(21) H(21ca 49(3) . . . . no H(20ca C(20) C(21) H(21ca 49(3) . . . . no #--------------------------------------------------------