# 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_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Pavel Lhotak' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Jan Budka' ; ? # Address 2 ; ; ? # Footnote 2 ; 'Petra Curinova' '' '' 'Veronika Michlova' '' '' 'Michaela Pojarova' '' '' 'Ivan Stibor' '' '' ; M.Tkadlecova ; '' '' _publ_contact_author_name 'Pavel Lhotak' _publ_contact_author_email LHOTAKP@VSCHT.CZ _publ_section_title ; The Systematic Approach to the New Ligands for Anion Recognition Based on Ureido-calix[4]arenes ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _publ_contact_author_address ; Chemical Crystallography Laboratory, Department of Chemistry, University of Nowhere, Nowhere, NO1 4T, UK. ; _publ_contact_author_fax '+44 1865 000000' _publ_contact_author_phone '+44 1865 000000' # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. The figures will be sent by e-mail. ; _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' # Attachment 'JB402.cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 678255' _audit_creation_date 06-07-13 _audit_creation_method CRYSTALS_ver_12.83 _oxford_structure_analysis_title ? _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 15.2890(2) _cell_length_b 17.4580(2) _cell_length_c 18.7830(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5013.47(10) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C54 H60 N4 O6 # Dc = 1.14 Fooo = 1984.00 Mu = 0.74 M = 861.09 # Found Formula = C56 H68.00 N4 O8 # Dc = 1.23 FOOO = 1984.00 Mu = 0.82 M = 925.18 _chemical_formula_sum 'C56 H68.00 N4 O8' _chemical_formula_moiety 'C56 H68.00 N4 O8' _chemical_compound_source ? _chemical_formula_weight 925.18 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1984 _exptl_absorpt_coefficient_mu 0.082 # Sheldrick geometric approximatio 0.98 0.98 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9758 _exptl_absorpt_correction_T_max 0.9758 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 11474 _reflns_number_total 6300 _diffrn_reflns_av_R_equivalents 0.012 # Number of reflections with Friedels Law is 6300 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5740 _diffrn_reflns_theta_min 1.717 _diffrn_reflns_theta_max 27.469 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.469 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min 0 _reflns_limit_h_max 19 _reflns_limit_k_min 0 _reflns_limit_k_max 22 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _oxford_diffrn_Wilson_B_factor 2.81 _oxford_diffrn_Wilson_scale 2.55 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.24 _refine_diff_density_max 0.43 _refine_ls_number_reflns 5689 _refine_ls_number_restraints 40 _refine_ls_number_parameters 649 #_refine_ls_R_factor_ref 0.0397 _refine_ls_wR_factor_ref 0.0474 _refine_ls_goodness_of_fit_ref 1.0463 #_reflns_number_all 6274 _refine_ls_R_factor_all 0.0449 _refine_ls_wR_factor_all 0.0524 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5689 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_gt 0.0474 _refine_ls_shift/su_max 0.000502 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.13 0.798 0.721 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N1 N 0.78146(12) 0.86898(9) 0.77935(9) 0.0339 1.0000 Uani . . . . . . N2 N 0.73594(13) 0.99150(10) 0.79827(9) 0.0351 1.0000 Uani . . . . . . N3 N 0.39095(11) 0.43036(9) 0.49246(8) 0.0297 1.0000 Uani . . . . . . N4 N 0.29710(13) 0.33159(10) 0.47164(9) 0.0367 1.0000 Uani . . . . . . O1 O 0.89206(10) 0.59587(8) 0.65332(8) 0.0368 1.0000 Uani . . . . . . O2 O 0.69480(9) 0.76260(7) 0.55312(7) 0.0277 1.0000 Uani . . . . . . O3 O 0.58688(8) 0.65278(7) 0.63349(7) 0.0253 1.0000 Uani . . . . . . O5 O 0.80886(12) 0.96110(9) 0.69559(8) 0.0455 1.0000 Uani . . . . . . O6 O 0.29450(10) 0.39321(8) 0.57915(7) 0.0348 1.0000 Uani . . . . . . O7 O 0.38683(14) 0.27649(12) 0.32003(12) 0.0631 1.0000 Uani . . . . . . O8 O 0.43075(13) 0.43053(11) 0.34439(10) 0.0529 1.0000 Uani . . . . . . C1 C 0.76581(13) 0.53634(10) 0.76771(10) 0.0283 1.0000 Uani D . . . . . C2 C 0.83141(14) 0.59266(11) 0.79812(11) 0.0339 1.0000 Uani . . . . . . C3 C 0.83632(13) 0.66536(11) 0.75381(10) 0.0309 1.0000 Uani . . . . . . C4 C 0.81059(13) 0.73469(11) 0.78382(10) 0.0309 1.0000 Uani . . . . . . C5 C 0.81130(12) 0.80226(11) 0.74412(10) 0.0301 1.0000 Uani . . . . . . C6 C 0.83509(13) 0.79987(11) 0.67267(11) 0.0310 1.0000 Uani . . . . . . C7 C 0.85962(12) 0.73074(11) 0.64118(10) 0.0296 1.0000 Uani . . . . . . C8 C 0.88033(12) 0.72928(11) 0.56187(10) 0.0304 1.0000 Uani . . . . . . C9 C 0.81620(12) 0.68426(10) 0.51641(10) 0.0286 1.0000 Uani . . . . . . C10 C 0.84613(14) 0.62555(13) 0.47290(12) 0.0386 1.0000 Uani . . . . . . C11 C 0.78990(16) 0.58244(13) 0.43186(13) 0.0437 1.0000 Uani . . . . . . C12 C 0.69984(14) 0.59541(12) 0.43593(11) 0.0371 1.0000 Uani . . . . . . C13 C 0.66735(12) 0.65411(10) 0.47798(9) 0.0265 1.0000 Uani . . . . . . C14 C 0.56925(12) 0.66633(10) 0.48335(10) 0.0272 1.0000 Uani . . . . . . C15 C 0.52488(11) 0.60333(10) 0.52539(9) 0.0248 1.0000 Uani . . . . . . C16 C 0.47388(12) 0.54764(10) 0.49199(10) 0.0271 1.0000 Uani . . . . . . C17 C 0.43785(11) 0.48708(10) 0.53074(10) 0.0259 1.0000 Uani . . . . . . C18 C 0.45384(12) 0.48167(10) 0.60335(10) 0.0270 1.0000 Uani . . . . . . C19 C 0.50228(11) 0.53768(10) 0.63859(9) 0.0252 1.0000 Uani . . . . . . C20 C 0.52285(12) 0.53125(10) 0.71720(9) 0.0274 1.0000 Uani . . . . . . C21 C 0.61713(12) 0.50728(10) 0.72808(9) 0.0263 1.0000 Uani D . . . . . C22 C 0.64892(13) 0.44055(10) 0.69633(10) 0.0312 1.0000 Uani . . . . . . C23 C 0.73574(14) 0.42059(10) 0.70161(11) 0.0342 1.0000 Uani . . . . . . C24 C 0.79414(13) 0.46862(11) 0.73627(11) 0.0332 1.0000 Uani . . . . . . C25 C 0.86357(13) 0.66467(11) 0.68244(11) 0.0319 1.0000 Uani . . . . . . C26 C 0.72623(12) 0.70020(10) 0.51537(9) 0.0255 1.0000 Uani . . . . . . C27 C 0.53653(11) 0.59850(9) 0.59904(9) 0.0237 1.0000 Uani . . . . . . C28 C 0.67607(13) 0.55274(10) 0.76661(9) 0.0273 1.0000 Uani D . . . . . C29 C 0.98640(17) 0.58688(15) 0.65418(16) 0.0510 1.0000 Uani . . . . . . C30 C 1.00899(19) 0.50368(16) 0.64276(17) 0.0572 1.0000 Uani . . . . . . C31 C 0.9667(2) 0.46845(19) 0.5779(2) 0.0717 1.0000 Uani . . . . . . C32 C 0.69937(13) 0.83320(11) 0.51481(11) 0.0327 1.0000 Uani . . . . . . C33 C 0.65457(16) 0.89492(12) 0.55820(12) 0.0391 1.0000 Uani . . . . . . C34 C 0.6708(2) 0.97372(13) 0.52625(16) 0.0544 1.0000 Uani . . . . . . C35 C 0.53594(13) 0.71649(10) 0.65869(11) 0.0306 1.0000 Uani . . . . . . C36 C 0.59445(13) 0.76727(11) 0.70215(10) 0.0313 1.0000 Uani . . . . . . C37 C 0.54604(17) 0.83789(13) 0.72868(14) 0.0470 1.0000 Uani . . . . . . C41 C 0.77823(14) 0.94173(11) 0.75329(10) 0.0330 1.0000 Uani . . . . . . C42 C 0.72177(13) 1.07002(11) 0.78537(11) 0.0323 1.0000 Uani . . . . . . C43 C 0.71854(16) 1.11832(12) 0.84440(12) 0.0390 1.0000 Uani . . . . . . C44 C 0.70312(17) 1.19628(12) 0.83653(14) 0.0444 1.0000 Uani . . . . . . C45 C 0.68912(15) 1.22648(13) 0.76964(15) 0.0472 1.0000 Uani . . . . . . C46 C 0.69091(16) 1.17855(15) 0.71094(14) 0.0461 1.0000 Uani . . . . . . C47 C 0.70721(16) 1.10043(14) 0.71795(12) 0.0421 1.0000 Uani . . . . . . C48 C 0.32612(12) 0.38594(11) 0.51903(10) 0.0288 1.0000 Uani . . . . . . C49 C 0.23280(15) 0.27574(12) 0.48780(10) 0.0357 1.0000 Uani . . . . . . C50 C 0.24625(18) 0.20082(14) 0.46505(12) 0.0459 1.0000 Uani . . . . . . C51 C 0.1839(2) 0.14495(15) 0.47889(14) 0.0590 1.0000 Uani . . . . . . C52 C 0.1081(2) 0.16352(18) 0.51562(14) 0.0603 1.0000 Uani . . . . . . C53 C 0.09400(18) 0.2383(2) 0.53724(14) 0.0583 1.0000 Uani . . . . . . C54 C 0.15572(16) 0.29537(15) 0.52342(12) 0.0443 1.0000 Uani . . . . . . C55 C 0.44142(19) 0.21692(18) 0.29384(17) 0.0580 1.0000 Uani . . . . . . C56 C 0.4295(2) 0.20043(19) 0.21638(17) 0.0625 1.0000 Uani . . . . . . O4 O 0.6458(7) 0.6141(4) 0.8042(5) 0.0250 0.7000 Uani D U . 1 1 . C38 C 0.5950(4) 0.5989(2) 0.8668(2) 0.0441 0.7000 Uani D U . 1 1 . C39 C 0.5287(3) 0.6647(3) 0.8807(2) 0.0526 0.7000 Uani D U . 1 1 . C40 C 0.5759(3) 0.7362(3) 0.9013(2) 0.0609 0.7000 Uani D U . 1 1 . O104 O 0.6472(18) 0.6265(10) 0.7939(11) 0.0257 0.3000 Uani D U . 1 2 . C138 C 0.6350(5) 0.6119(5) 0.8729(4) 0.0288 0.3000 Uani D U . 1 2 . C139 C 0.5899(4) 0.6822(4) 0.9013(3) 0.0268 0.3000 Uani D U . 1 2 . C140 C 0.4974(5) 0.6999(5) 0.8724(4) 0.0391 0.3000 Uani D U . 1 2 . H564 H 0.8164 0.6083 0.8486 0.0434 1.0000 Uiso . . . . . . H22 H 0.8886 0.5681 0.7983 0.0433 1.0000 Uiso . . . . . . H41 H 0.7906 0.7360 0.8323 0.0395 1.0000 Uiso . . . . . . H61 H 0.8332 0.8463 0.6447 0.0396 1.0000 Uiso . . . . . . H81 H 0.8801 0.7817 0.5450 0.0392 1.0000 Uiso . . . . . . H82 H 0.9404 0.7067 0.5542 0.0395 1.0000 Uiso . . . . . . H101 H 0.9091 0.6140 0.4738 0.0494 1.0000 Uiso . . . . . . H111 H 0.8129 0.5440 0.3996 0.0568 1.0000 Uiso . . . . . . H121 H 0.6596 0.5621 0.4106 0.0478 1.0000 Uiso . . . . . . H141 H 0.5583 0.7167 0.5064 0.0333 1.0000 Uiso . . . . . . H142 H 0.5457 0.6667 0.4340 0.0330 1.0000 Uiso . . . . . . H161 H 0.4628 0.5513 0.4405 0.0333 1.0000 Uiso . . . . . . H181 H 0.4312 0.4384 0.6295 0.0343 1.0000 Uiso . . . . . . H201 H 0.5144 0.5824 0.7405 0.0355 1.0000 Uiso . . . . . . H202 H 0.4823 0.4912 0.7386 0.0351 1.0000 Uiso . . . . . . H221 H 0.6082 0.4091 0.6687 0.0401 1.0000 Uiso . . . . . . H231 H 0.7570 0.3725 0.6822 0.0435 1.0000 Uiso . . . . . . H241 H 0.8558 0.4552 0.7391 0.0423 1.0000 Uiso . . . . . . H291 H 1.0098 0.6075 0.7017 0.0724 1.0000 Uiso . . . . . . H292 H 1.0123 0.6204 0.6139 0.0721 1.0000 Uiso . . . . . . H301 H 1.0742 0.4971 0.6355 0.0728 1.0000 Uiso . . . . . . H302 H 0.9906 0.4714 0.6869 0.0740 1.0000 Uiso . . . . . . H311 H 0.9850 0.4145 0.5745 0.1132 1.0000 Uiso . . . . . . H312 H 0.9827 0.4973 0.5342 0.1135 1.0000 Uiso . . . . . . H313 H 0.9015 0.4707 0.5864 0.1128 1.0000 Uiso . . . . . . H321 H 0.7610 0.8473 0.5072 0.0431 1.0000 Uiso . . . . . . H322 H 0.6716 0.8262 0.4668 0.0433 1.0000 Uiso . . . . . . H331 H 0.6793 0.8938 0.6075 0.0523 1.0000 Uiso . . . . . . H332 H 0.5896 0.8826 0.5598 0.0522 1.0000 Uiso . . . . . . H341 H 0.6369 1.0133 0.5532 0.0920 1.0000 Uiso . . . . . . H342 H 0.7328 0.9861 0.5268 0.0923 1.0000 Uiso . . . . . . H343 H 0.6497 0.9727 0.4764 0.0923 1.0000 Uiso . . . . . . H351 H 0.4834 0.6975 0.6867 0.0408 1.0000 Uiso . . . . . . H352 H 0.5130 0.7467 0.6179 0.0414 1.0000 Uiso . . . . . . H361 H 0.6173 0.7352 0.7431 0.0415 1.0000 Uiso . . . . . . H362 H 0.6455 0.7825 0.6709 0.0415 1.0000 Uiso . . . . . . H371 H 0.5849 0.8715 0.7540 0.0766 1.0000 Uiso . . . . . . H372 H 0.4993 0.8218 0.7617 0.0777 1.0000 Uiso . . . . . . H373 H 0.5205 0.8667 0.6885 0.0771 1.0000 Uiso . . . . . . H431 H 0.7287 1.0967 0.8921 0.0506 1.0000 Uiso . . . . . . H441 H 0.7024 1.2298 0.8792 0.0581 1.0000 Uiso . . . . . . H451 H 0.6776 1.2816 0.7630 0.0573 1.0000 Uiso . . . . . . H461 H 0.6809 1.1988 0.6633 0.0617 1.0000 Uiso . . . . . . H471 H 0.7085 1.0670 0.6760 0.0575 1.0000 Uiso . . . . . . H501 H 0.3003 0.1894 0.4388 0.0597 1.0000 Uiso . . . . . . H511 H 0.1932 0.0930 0.4624 0.0726 1.0000 Uiso . . . . . . H521 H 0.0672 0.1236 0.5256 0.0785 1.0000 Uiso . . . . . . H531 H 0.0403 0.2517 0.5628 0.0769 1.0000 Uiso . . . . . . H541 H 0.1460 0.3487 0.5394 0.0556 1.0000 Uiso . . . . . . H551 H 0.5019 0.2407 0.2981 0.0771 1.0000 Uiso . . . . . . H552 H 0.4372 0.1676 0.3220 0.0776 1.0000 Uiso . . . . . . H561 H 0.4710 0.1594 0.2020 0.1019 1.0000 Uiso . . . . . . H562 H 0.4402 0.2496 0.1879 0.1015 1.0000 Uiso . . . . . . H563 H 0.3680 0.1808 0.2080 0.1013 1.0000 Uiso . . . . . . H12 H 0.7181 0.9728 0.8403 0.0463 1.0000 Uiso . . . . . . H15 H 0.7629 0.8634 0.8253 0.0422 1.0000 Uiso . . . . . . H21 H 0.4028 0.4252 0.4460 0.0393 1.0000 Uiso . . . . . . H23 H 0.3244 0.3279 0.4289 0.0473 1.0000 Uiso . . . . . . H65 H 0.4003 0.3141 0.2866 0.1055 1.0000 Uiso . . . . . . H401 H 0.5399 0.7793 0.9045 0.0939 0.7000 Uiso . . . 1 1 . H402 H 0.6072 0.7237 0.9467 0.0946 0.7000 Uiso . . . 1 1 . H403 H 0.6232 0.7444 0.8630 0.0945 0.7000 Uiso . . . 1 1 . H1401 H 0.4735 0.7449 0.8951 0.0681 0.3000 Uiso . . . 1 2 . H1402 H 0.4581 0.6564 0.8810 0.0679 0.3000 Uiso . . . 1 2 . H1403 H 0.5015 0.7085 0.8223 0.0680 0.3000 Uiso . . . 1 2 . H1381 H 0.6915 0.6045 0.8972 0.0549 0.3000 Uiso . . . 1 2 . H1382 H 0.5987 0.5661 0.8834 0.0552 0.3000 Uiso . . . 1 2 . H1391 H 0.5853 0.6761 0.9547 0.0439 0.3000 Uiso . . . 1 2 . H1392 H 0.6297 0.7242 0.8911 0.0445 0.3000 Uiso . . . 1 2 . H381 H 0.6367 0.5964 0.9070 0.0656 0.7000 Uiso . . . 1 1 . H382 H 0.5670 0.5479 0.8629 0.0652 0.7000 Uiso . . . 1 1 . H391 H 0.4891 0.6501 0.9214 0.0667 0.7000 Uiso . . . 1 1 . H392 H 0.4921 0.6737 0.8384 0.0664 0.7000 Uiso . . . 1 1 . H1 H 0.3970 0.3857 0.3510 0.0868 1.0000 Uiso . . . . . . H6 H 0.3835 0.4586 0.3340 0.0885 1.0000 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0447(9) 0.0269(7) 0.0301(7) -0.0029(6) 0.0031(7) -0.0026(7) N2 0.0500(10) 0.0268(7) 0.0284(7) 0.0003(6) 0.0032(7) -0.0022(7) N3 0.0339(8) 0.0277(7) 0.0276(7) -0.0030(6) 0.0011(6) -0.0038(6) N4 0.0463(10) 0.0353(8) 0.0285(7) -0.0062(7) 0.0027(7) -0.0134(8) O1 0.0386(7) 0.0298(7) 0.0419(7) -0.0055(6) 0.0005(6) 0.0013(6) O2 0.0333(6) 0.0204(5) 0.0295(6) 0.0000(5) 0.0050(5) 0.0002(5) O3 0.0263(6) 0.0204(5) 0.0292(6) -0.0024(5) -0.0001(5) -0.0010(5) O5 0.0686(11) 0.0318(7) 0.0361(7) -0.0007(6) 0.0135(7) -0.0036(7) O6 0.0398(7) 0.0332(7) 0.0315(6) -0.0067(5) 0.0054(6) -0.0105(6) O7 0.0615(11) 0.0569(11) 0.0709(12) -0.0101(10) -0.0034(10) 0.0015(10) O8 0.0571(10) 0.0582(10) 0.0432(9) -0.0022(8) -0.0003(8) 0.0102(9) C1 0.0340(9) 0.0242(8) 0.0268(8) 0.0028(7) -0.0033(7) 0.0015(7) C2 0.0379(10) 0.0283(9) 0.0355(9) -0.0001(7) -0.0090(8) -0.0006(8) C3 0.0308(9) 0.0282(8) 0.0337(9) -0.0006(7) -0.0078(7) -0.0018(7) C4 0.0325(9) 0.0297(9) 0.0305(8) -0.0022(7) -0.0047(7) -0.0033(7) C5 0.0284(9) 0.0275(8) 0.0343(9) -0.0040(7) -0.0028(7) -0.0039(7) C6 0.0296(9) 0.0284(8) 0.0349(9) -0.0014(8) -0.0023(7) -0.0040(7) C7 0.0256(8) 0.0316(9) 0.0316(9) -0.0022(7) -0.0020(7) -0.0040(7) C8 0.0269(8) 0.0322(9) 0.0323(9) -0.0018(7) 0.0023(7) -0.0036(7) C9 0.0287(9) 0.0286(8) 0.0285(8) -0.0017(7) 0.0033(7) -0.0024(7) C10 0.0312(10) 0.0429(11) 0.0417(10) -0.0103(9) 0.0036(8) 0.0055(8) C11 0.0434(12) 0.0420(11) 0.0458(11) -0.0205(10) 0.0031(10) 0.0073(9) C12 0.0395(10) 0.0355(9) 0.0364(10) -0.0110(8) -0.0016(8) -0.0007(9) C13 0.0284(8) 0.0266(8) 0.0245(8) 0.0007(7) 0.0017(7) -0.0008(7) C14 0.0281(8) 0.0244(8) 0.0290(8) 0.0036(7) -0.0006(7) -0.0020(7) C15 0.0234(8) 0.0232(7) 0.0279(8) 0.0020(6) 0.0023(6) 0.0003(6) C16 0.0278(8) 0.0266(8) 0.0269(8) -0.0005(7) -0.0018(7) 0.0011(7) C17 0.0241(8) 0.0240(8) 0.0298(8) -0.0025(7) -0.0008(7) -0.0005(6) C18 0.0294(9) 0.0224(8) 0.0292(8) 0.0019(7) 0.0015(7) -0.0035(7) C19 0.0256(8) 0.0226(7) 0.0275(8) -0.0001(6) 0.0002(6) 0.0000(7) C20 0.0302(9) 0.0267(8) 0.0252(8) 0.0012(6) 0.0016(7) -0.0024(7) C21 0.0322(8) 0.0234(8) 0.0232(7) 0.0036(6) 0.0005(7) -0.0011(7) C22 0.0384(10) 0.0232(8) 0.0321(9) 0.0000(7) 0.0011(8) -0.0044(7) C23 0.0438(10) 0.0208(8) 0.0381(9) -0.0012(7) 0.0026(8) 0.0019(7) C24 0.0356(9) 0.0254(8) 0.0386(10) 0.0019(7) -0.0011(8) 0.0035(7) C25 0.0310(9) 0.0275(8) 0.0371(9) -0.0042(7) -0.0038(7) -0.0018(7) C26 0.0322(9) 0.0212(7) 0.0232(7) 0.0003(6) 0.0030(7) -0.0011(7) C27 0.0220(7) 0.0216(7) 0.0275(8) -0.0011(6) 0.0013(6) 0.0006(6) C28 0.0368(9) 0.0207(7) 0.0245(8) 0.0007(6) -0.0013(7) 0.0009(7) C29 0.0433(12) 0.0461(12) 0.0636(15) -0.0046(12) 0.0005(11) 0.0084(10) C30 0.0516(14) 0.0505(14) 0.0694(17) 0.0008(13) 0.0121(13) 0.0140(12) C31 0.072(2) 0.0582(16) 0.085(2) -0.0184(16) 0.0086(17) 0.0141(15) C32 0.0358(9) 0.0239(8) 0.0383(9) 0.0050(8) 0.0016(8) -0.0013(7) C33 0.0453(11) 0.0261(9) 0.0460(11) -0.0026(8) 0.0009(9) 0.0021(8) C34 0.0704(17) 0.0270(10) 0.0659(16) 0.0050(10) -0.0055(14) -0.0006(10) C35 0.0290(8) 0.0246(8) 0.0381(9) -0.0058(7) 0.0013(8) 0.0037(7) C36 0.0345(9) 0.0265(8) 0.0330(9) -0.0041(7) 0.0015(8) 0.0016(7) C37 0.0545(13) 0.0363(10) 0.0501(13) -0.0178(10) -0.0008(11) 0.0084(10) C41 0.0399(10) 0.0278(8) 0.0312(9) -0.0014(7) 0.0019(8) -0.0058(8) C42 0.0339(9) 0.0290(8) 0.0341(9) 0.0017(7) 0.0007(8) -0.0017(7) C43 0.0459(11) 0.0328(10) 0.0384(10) -0.0001(8) -0.0056(9) 0.0020(9) C44 0.0464(12) 0.0305(10) 0.0562(13) -0.0008(9) -0.0019(11) 0.0036(9) C45 0.0371(11) 0.0347(10) 0.0697(15) 0.0141(11) 0.0090(11) 0.0022(9) C46 0.0395(11) 0.0512(13) 0.0477(12) 0.0215(11) 0.0034(10) 0.0050(10) C47 0.0450(11) 0.0444(11) 0.0369(10) 0.0077(9) 0.0002(9) -0.0016(10) C48 0.0304(9) 0.0261(8) 0.0300(8) -0.0021(7) -0.0031(7) -0.0026(7) C49 0.0460(11) 0.0349(9) 0.0263(8) 0.0008(8) -0.0097(8) -0.0131(8) C50 0.0618(14) 0.0382(11) 0.0378(11) -0.0063(9) -0.0108(10) -0.0156(10) C51 0.086(2) 0.0449(13) 0.0458(13) 0.0034(11) -0.0214(14) -0.0308(14) C52 0.0710(17) 0.0668(17) 0.0432(12) 0.0133(12) -0.0193(13) -0.0437(15) C53 0.0480(14) 0.086(2) 0.0410(12) 0.0054(13) -0.0093(10) -0.0262(14) C54 0.0416(11) 0.0536(13) 0.0375(10) -0.0018(10) -0.0077(9) -0.0116(10) C55 0.0488(13) 0.0571(15) 0.0683(17) -0.0068(13) 0.0025(13) -0.0005(12) C56 0.0617(16) 0.0610(16) 0.0648(17) -0.0062(14) 0.0173(14) -0.0149(14) O4 0.0353(14) 0.016(3) 0.024(3) 0.0053(17) -0.0010(17) 0.0030(17) C38 0.068(3) 0.0355(18) 0.0289(16) -0.0001(13) 0.008(2) 0.005(2) C39 0.054(2) 0.062(2) 0.0414(19) -0.0064(18) 0.0094(17) -0.004(2) C40 0.070(3) 0.061(3) 0.052(2) -0.0147(19) 0.0024(19) 0.006(2) O104 0.051(4) 0.010(5) 0.016(4) 0.007(3) -0.004(3) 0.002(4) C138 0.029(3) 0.028(3) 0.029(3) -0.009(2) -0.002(3) -0.001(3) C139 0.030(3) 0.024(3) 0.027(3) -0.014(2) 0.004(2) 0.006(2) C140 0.036(3) 0.051(4) 0.030(3) -0.002(3) -0.001(3) 0.031(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.6124(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C5 . 1.415(2) yes N1 . C41 . 1.362(3) yes N1 . H15 . 0.914 no N2 . C41 . 1.373(3) yes N2 . C42 . 1.409(3) yes N2 . H12 . 0.896 no N3 . C17 . 1.418(2) yes N3 . C48 . 1.354(2) yes N3 . H21 . 0.895 no N4 . C48 . 1.375(2) yes N4 . C49 . 1.418(3) yes N4 . H23 . 0.908 no O1 . C25 . 1.390(2) yes O1 . C29 . 1.451(3) yes O2 . C26 . 1.386(2) yes O2 . C32 . 1.429(2) yes O3 . C27 . 1.382(2) yes O3 . C35 . 1.438(2) yes O5 . C41 . 1.228(3) yes O6 . C48 . 1.235(2) yes O7 . C55 . 1.421(4) yes O7 . H65 . 0.931 no O8 . H1 . 0.946 no O8 . H6 . 0.894 no C1 . C2 . 1.516(3) yes C1 . C24 . 1.391(3) yes C1 . C28 . 1.402(3) yes C2 . C3 . 1.520(3) yes C2 . H564 . 1.014 no C2 . H22 . 0.974 no C3 . C4 . 1.392(3) yes C3 . C25 . 1.404(3) yes C4 . C5 . 1.396(3) yes C4 . H41 . 0.961 no C5 . C6 . 1.391(3) yes C6 . C7 . 1.395(3) yes C6 . H61 . 0.966 no C7 . C8 . 1.523(3) yes C7 . C25 . 1.391(3) yes C8 . C9 . 1.519(3) yes C8 . H81 . 0.969 no C8 . H82 . 1.010 no C9 . C10 . 1.389(3) yes C9 . C26 . 1.404(3) yes C10 . C11 . 1.378(3) yes C10 . H101 . 0.984 no C11 . C12 . 1.398(3) yes C11 . H111 . 0.969 no C12 . C13 . 1.386(3) yes C12 . H121 . 0.971 no C13 . C14 . 1.518(2) yes C13 . C26 . 1.397(3) yes C14 . C15 . 1.514(2) yes C14 . H141 . 0.994 no C14 . H142 . 0.995 no C15 . C16 . 1.395(3) yes C15 . C27 . 1.397(2) yes C16 . C17 . 1.397(3) yes C16 . H161 . 0.983 no C17 . C18 . 1.389(3) yes C18 . C19 . 1.394(2) yes C18 . H181 . 0.965 no C19 . C20 . 1.514(2) yes C19 . C27 . 1.398(2) yes C20 . C21 . 1.515(3) yes C20 . H201 . 1.003 no C20 . H202 . 1.017 no C21 . C22 . 1.396(3) yes C21 . C28 . 1.402(3) yes C22 . C23 . 1.376(3) yes C22 . H221 . 0.979 no C23 . C24 . 1.387(3) yes C23 . H231 . 0.971 no C24 . H241 . 0.972 no C28 . O4 . 1.364(8) yes C28 . O104 . 1.454(19) yes C29 . C30 . 1.508(4) yes C29 . H291 . 1.027 no C29 . H292 . 1.035 no C30 . C31 . 1.510(5) yes C30 . H301 . 1.013 no C30 . H302 . 1.041 no C31 . H311 . 0.984 no C31 . H312 . 0.994 no C31 . H313 . 1.010 no C32 . C33 . 1.515(3) yes C32 . H321 . 0.984 no C32 . H322 . 1.004 no C33 . C34 . 1.521(3) yes C33 . H331 . 1.000 no C33 . H332 . 1.016 no C34 . H341 . 1.000 no C34 . H342 . 0.972 no C34 . H343 . 0.990 no C35 . C36 . 1.501(3) yes C35 . H351 . 1.016 no C35 . H352 . 0.994 no C36 . C37 . 1.522(3) yes C36 . H361 . 1.014 no C36 . H362 . 1.012 no C37 . H371 . 0.961 no C37 . H372 . 0.987 no C37 . H373 . 0.988 no C42 . C43 . 1.394(3) yes C42 . C47 . 1.391(3) yes C43 . C44 . 1.389(3) yes C43 . H431 . 0.985 no C44 . C45 . 1.379(4) yes C44 . H441 . 0.993 no C45 . C46 . 1.384(4) yes C45 . H451 . 0.986 no C46 . C47 . 1.393(3) yes C46 . H461 . 0.975 no C47 . H471 . 0.980 no C49 . C50 . 1.391(3) yes C49 . C54 . 1.398(3) yes C50 . C51 . 1.388(3) yes C50 . H501 . 0.982 no C51 . C52 . 1.387(5) yes C51 . H511 . 0.968 no C52 . C53 . 1.385(5) yes C52 . H521 . 0.955 no C53 . C54 . 1.396(4) yes C53 . H531 . 0.979 no C54 . H541 . 0.989 no C55 . C56 . 1.494(5) yes C55 . H551 . 1.017 no C55 . H552 . 1.013 no C56 . H561 . 0.994 no C56 . H562 . 1.025 no C56 . H563 . 1.014 no O4 . C38 . 1.434(9) yes C38 . C39 . 1.554(7) yes C38 . H381 . 0.990 no C38 . H382 . 0.990 no C39 . C40 . 1.493(6) yes C39 . H391 . 1.008 no C39 . H392 . 0.984 no C40 . H401 . 0.935 no C40 . H402 . 1.002 no C40 . H403 . 1.029 no O104 . C138 . 1.52(2) yes C138 . C139 . 1.506(9) yes C138 . H1381 . 0.985 no C138 . H1382 . 0.992 no C139 . C140 . 1.547(9) yes C139 . H1391 . 1.010 no C139 . H1392 . 0.972 no C140 . H1401 . 0.966 no C140 . H1402 . 0.982 no C140 . H1403 . 0.955 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 . N1 . C41 . 127.67(17) yes C5 . N1 . H15 . 117.0 no C41 . N1 . H15 . 115.3 no C41 . N2 . C42 . 125.60(17) yes C41 . N2 . H12 . 117.1 no C42 . N2 . H12 . 117.3 no C17 . N3 . C48 . 125.67(15) yes C17 . N3 . H21 . 117.5 no C48 . N3 . H21 . 116.8 no C48 . N4 . C49 . 124.06(17) yes C48 . N4 . H23 . 118.2 no C49 . N4 . H23 . 117.4 no C25 . O1 . C29 . 113.62(17) yes C26 . O2 . C32 . 113.80(14) yes C27 . O3 . C35 . 112.50(13) yes C55 . O7 . H65 . 98.8 no H1 . O8 . H6 . 92.4 no C2 . C1 . C24 . 120.34(18) yes C2 . C1 . C28 . 121.37(16) yes C24 . C1 . C28 . 118.18(17) yes C1 . C2 . C3 . 111.59(16) yes C1 . C2 . H564 . 112.2 no C3 . C2 . H564 . 107.4 no C1 . C2 . H22 . 108.0 no C3 . C2 . H22 . 109.0 no H564 . C2 . H22 . 108.6 no C2 . C3 . C4 . 119.37(17) yes C2 . C3 . C25 . 122.03(18) yes C4 . C3 . C25 . 118.56(18) yes C3 . C4 . C5 . 121.10(17) yes C3 . C4 . H41 . 119.7 no C5 . C4 . H41 . 119.2 no N1 . C5 . C4 . 116.32(17) yes N1 . C5 . C6 . 124.06(18) yes C4 . C5 . C6 . 119.48(18) yes C5 . C6 . C7 . 120.34(18) yes C5 . C6 . H61 . 119.4 no C7 . C6 . H61 . 120.3 no C6 . C7 . C8 . 119.00(17) yes C6 . C7 . C25 . 119.53(17) yes C8 . C7 . C25 . 121.46(17) yes C7 . C8 . C9 . 115.09(15) yes C7 . C8 . H81 . 107.7 no C9 . C8 . H81 . 107.6 no C7 . C8 . H82 . 109.6 no C9 . C8 . H82 . 107.7 no H81 . C8 . H82 . 109.0 no C8 . C9 . C10 . 120.01(17) yes C8 . C9 . C26 . 122.53(16) yes C10 . C9 . C26 . 117.46(17) yes C9 . C10 . C11 . 121.79(19) yes C9 . C10 . H101 . 117.6 no C11 . C10 . H101 . 120.5 no C10 . C11 . C12 . 119.69(19) yes C10 . C11 . H111 . 120.1 no C12 . C11 . H111 . 120.2 no C11 . C12 . C13 . 120.28(18) yes C11 . C12 . H121 . 120.1 no C13 . C12 . H121 . 119.6 no C12 . C13 . C14 . 119.73(17) yes C12 . C13 . C26 . 118.78(17) yes C14 . C13 . C26 . 121.48(16) yes C13 . C14 . C15 . 112.03(15) yes C13 . C14 . H141 . 108.6 no C15 . C14 . H141 . 109.8 no C13 . C14 . H142 . 107.2 no C15 . C14 . H142 . 109.1 no H141 . C14 . H142 . 109.9 no C14 . C15 . C16 . 121.47(16) yes C14 . C15 . C27 . 120.19(16) yes C16 . C15 . C27 . 118.31(16) yes C15 . C16 . C17 . 120.90(16) yes C15 . C16 . H161 . 119.5 no C17 . C16 . H161 . 119.6 no N3 . C17 . C16 . 117.62(16) yes N3 . C17 . C18 . 122.64(16) yes C16 . C17 . C18 . 119.59(16) yes C17 . C18 . C19 . 120.81(16) yes C17 . C18 . H181 . 119.3 no C19 . C18 . H181 . 119.9 no C18 . C19 . C20 . 121.44(15) yes C18 . C19 . C27 . 118.66(16) yes C20 . C19 . C27 . 119.80(16) yes C19 . C20 . C21 . 110.48(14) yes C19 . C20 . H201 . 109.5 no C21 . C20 . H201 . 108.0 no C19 . C20 . H202 . 108.0 no C21 . C20 . H202 . 109.7 no H201 . C20 . H202 . 111.2 no C20 . C21 . C22 . 120.28(16) yes C20 . C21 . C28 . 121.65(16) yes C22 . C21 . C28 . 117.98(17) yes C21 . C22 . C23 . 121.09(18) yes C21 . C22 . H221 . 118.2 no C23 . C22 . H221 . 120.7 no C22 . C23 . C24 . 120.11(18) yes C22 . C23 . H231 . 121.0 no C24 . C23 . H231 . 118.9 no C1 . C24 . C23 . 120.85(18) yes C1 . C24 . H241 . 118.9 no C23 . C24 . H241 . 120.3 no C3 . C25 . C7 . 120.79(18) yes C3 . C25 . O1 . 118.44(17) yes C7 . C25 . O1 . 120.74(17) yes C9 . C26 . C13 . 121.63(16) yes C9 . C26 . O2 . 119.25(16) yes C13 . C26 . O2 . 119.12(16) yes C19 . C27 . C15 . 121.62(16) yes C19 . C27 . O3 . 118.74(15) yes C15 . C27 . O3 . 119.56(15) yes C21 . C28 . C1 . 121.40(17) yes C21 . C28 . O4 . 119.6(5) yes C1 . C28 . O4 . 119.0(5) yes C21 . C28 . C1 . 121.40(17) yes C21 . C28 . O104 . 119.2(11) yes C1 . C28 . O104 . 118.2(11) yes O1 . C29 . C30 . 109.3(2) yes O1 . C29 . H291 . 108.5 no C30 . C29 . H291 . 112.4 no O1 . C29 . H292 . 108.1 no C30 . C29 . H292 . 110.7 no H291 . C29 . H292 . 107.7 no C29 . C30 . C31 . 114.1(3) yes C29 . C30 . H301 . 110.7 no C31 . C30 . H301 . 105.5 no C29 . C30 . H302 . 110.2 no C31 . C30 . H302 . 107.9 no H301 . C30 . H302 . 108.2 no C30 . C31 . H311 . 108.7 no C30 . C31 . H312 . 110.8 no H311 . C31 . H312 . 111.1 no C30 . C31 . H313 . 106.3 no H311 . C31 . H313 . 109.2 no H312 . C31 . H313 . 110.7 no O2 . C32 . C33 . 108.69(16) yes O2 . C32 . H321 . 109.6 no C33 . C32 . H321 . 109.4 no O2 . C32 . H322 . 109.0 no C33 . C32 . H322 . 112.2 no H321 . C32 . H322 . 107.8 no C32 . C33 . C34 . 110.9(2) yes C32 . C33 . H331 . 108.3 no C34 . C33 . H331 . 108.7 no C32 . C33 . H332 . 107.9 no C34 . C33 . H332 . 111.2 no H331 . C33 . H332 . 109.8 no C33 . C34 . H341 . 109.9 no C33 . C34 . H342 . 110.9 no H341 . C34 . H342 . 110.2 no C33 . C34 . H343 . 107.6 no H341 . C34 . H343 . 108.8 no H342 . C34 . H343 . 109.3 no O3 . C35 . C36 . 108.24(15) yes O3 . C35 . H351 . 110.3 no C36 . C35 . H351 . 112.5 no O3 . C35 . H352 . 110.3 no C36 . C35 . H352 . 108.5 no H351 . C35 . H352 . 107.0 no C35 . C36 . C37 . 111.51(17) yes C35 . C36 . H361 . 107.0 no C37 . C36 . H361 . 111.4 no C35 . C36 . H362 . 107.4 no C37 . C36 . H362 . 110.6 no H361 . C36 . H362 . 108.7 no C36 . C37 . H371 . 110.8 no C36 . C37 . H372 . 109.1 no H371 . C37 . H372 . 108.1 no C36 . C37 . H373 . 110.8 no H371 . C37 . H373 . 108.2 no H372 . C37 . H373 . 109.7 no N2 . C41 . N1 . 112.70(17) yes N2 . C41 . O5 . 123.24(18) yes N1 . C41 . O5 . 124.06(19) yes N2 . C42 . C43 . 117.22(18) yes N2 . C42 . C47 . 123.53(19) yes C43 . C42 . C47 . 119.18(19) yes C42 . C43 . C44 . 120.9(2) yes C42 . C43 . H431 . 119.1 no C44 . C43 . H431 . 119.9 no C43 . C44 . C45 . 119.9(2) yes C43 . C44 . H441 . 119.5 no C45 . C44 . H441 . 120.6 no C44 . C45 . C46 . 119.4(2) yes C44 . C45 . H451 . 121.1 no C46 . C45 . H451 . 119.5 no C45 . C46 . C47 . 121.3(2) yes C45 . C46 . H461 . 120.6 no C47 . C46 . H461 . 118.1 no C46 . C47 . C42 . 119.2(2) yes C46 . C47 . H471 . 120.7 no C42 . C47 . H471 . 120.1 no N4 . C48 . N3 . 113.14(16) yes N4 . C48 . O6 . 122.45(17) yes N3 . C48 . O6 . 124.40(17) yes N4 . C49 . C50 . 118.6(2) yes N4 . C49 . C54 . 121.2(2) yes C50 . C49 . C54 . 120.1(2) yes C49 . C50 . C51 . 120.1(3) yes C49 . C50 . H501 . 118.0 no C51 . C50 . H501 . 121.9 no C50 . C51 . C52 . 120.2(3) yes C50 . C51 . H511 . 119.8 no C52 . C51 . H511 . 120.0 no C51 . C52 . C53 . 119.8(2) yes C51 . C52 . H521 . 118.3 no C53 . C52 . H521 . 121.9 no C52 . C53 . C54 . 120.9(3) yes C52 . C53 . H531 . 119.9 no C54 . C53 . H531 . 119.3 no C49 . C54 . C53 . 118.9(2) yes C49 . C54 . H541 . 120.2 no C53 . C54 . H541 . 120.8 no O7 . C55 . C56 . 114.0(3) yes O7 . C55 . H551 . 102.0 no C56 . C55 . H551 . 105.4 no O7 . C55 . H552 . 113.8 no C56 . C55 . H552 . 109.7 no H551 . C55 . H552 . 111.4 no C55 . C56 . H561 . 109.0 no C55 . C56 . H562 . 109.2 no H561 . C56 . H562 . 111.1 no C55 . C56 . H563 . 109.3 no H561 . C56 . H563 . 107.8 no H562 . C56 . H563 . 110.4 no C28 . O4 . C38 . 117.5(6) yes O4 . C38 . C39 . 110.8(4) yes O4 . C38 . H381 . 106.5 no C39 . C38 . H381 . 108.9 no O4 . C38 . H382 . 109.9 no C39 . C38 . H382 . 113.2 no H381 . C38 . H382 . 107.2 no C38 . C39 . C40 . 110.2(4) yes C38 . C39 . H391 . 109.5 no C40 . C39 . H391 . 107.7 no C38 . C39 . H392 . 110.6 no C40 . C39 . H392 . 110.5 no H391 . C39 . H392 . 108.2 no C39 . C40 . H401 . 113.9 no C39 . C40 . H402 . 105.6 no H401 . C40 . H402 . 113.6 no C39 . C40 . H403 . 106.0 no H401 . C40 . H403 . 110.3 no H402 . C40 . H403 . 106.8 no C28 . O104 . C138 . 103.5(11) yes O104 . C138 . C139 . 105.4(9) yes O104 . C138 . H1381 . 111.5 no C139 . C138 . H1381 . 110.2 no O104 . C138 . H1382 . 113.4 no C139 . C138 . H1382 . 109.2 no H1381 . C138 . H1382 . 107.0 no C138 . C139 . C140 . 117.2(6) yes C138 . C139 . H1391 . 107.2 no C140 . C139 . H1391 . 107.9 no C138 . C139 . H1392 . 104.9 no C140 . C139 . H1392 . 110.7 no H1391 . C139 . H1392 . 108.7 no C139 . C140 . H1401 . 110.6 no C139 . C140 . H1402 . 110.3 no H1401 . C140 . H1402 . 108.9 no C139 . C140 . H1403 . 108.5 no H1401 . C140 . H1403 . 109.5 no H1402 . C140 . H1403 . 109.0 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N2 . H12 . O6 3_656 157 0.90 2.06 2.909(2) yes N1 . H15 . O6 3_656 158 0.91 2.06 2.931(2) yes N3 . H21 . O8 . 172 0.90 1.96 2.847(2) yes O8 . H1 . O7 . 143 0.95 2.00 2.809(2) yes O8 . H6 . O5 2_466 163 0.89 1.89 2.760(2) yes