# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Viktor Zhdankin' _publ_contact_author_email VZHDANKI@D.UMN.EDU _publ_section_title ; Preparation and X-ray crystal structure of 2-iodyl-N,N-dialkylaniline oxides: first entry into the heterocyclic system of benziodoxazole ; loop_ _publ_author_name 'Viktor Zhdankin' 'Rashad R Karimov' 'Zeinul-Gabiden Kazhkenov' 'Victor Nemykin' # Attachment '5b.cif' #============================================================================== data_1 _database_code_depnum_ccdc_archive 'CCDC 696745' _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 regularize 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 ; (type here to add preparation details) ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 8.1788(16) _cell_length_b 10.512(2) _cell_length_c 15.850(3) _cell_angle_alpha 71.58(3) _cell_angle_beta 82.16(3) _cell_angle_gamma 78.02(3) _cell_volume 1261.1(5) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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' I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776 4.0712 '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 = C11 H16 I1 N1 O3 # Dc = 1.78 Fooo = 664.00 Mu = 25.33 M = 674.31 # Found Formula = C11 H16 I1 N1 O3 # Dc = 1.78 FOOO = 664.00 Mu = 25.32 M = 674.31 _chemical_formula_sum 'C11 H16 I1 N1 O3' _chemical_formula_moiety 'C11 H16 I1 N1 O3' _chemical_compound_source ? _chemical_formula_weight 337.15 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 18 _cell_measurement_temperature 298 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.11 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_max 0.31 _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 2.532 # Sheldrick geometric approximatio 0.56 0.76 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_absorpt_correction_T_min 0.51 _exptl_absorpt_correction_T_max 0.76 _diffrn_measurement_device 'Rigaku AFC-7R' _diffrn_measurement_device_type 'Rigaku AFC-7R' _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 'Rigaku AFC-7R' _computing_cell_refinement 'Win AFC' _computing_data_reduction 'TexSan 10.3b' _computing_structure_solution 'CRYSTALS (Betteridge et al., 2003)' _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 150 _diffrn_standards_number 3 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 298 _diffrn_reflns_number 4429 _reflns_number_total 4429 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections with Friedels Law is 4429 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4439 _diffrn_reflns_theta_min 2.074 _diffrn_reflns_theta_max 24.993 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.993 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min -11 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.14 _refine_diff_density_max 1.49 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 2367 _refine_ls_number_restraints 1 _refine_ls_number_parameters 289 _oxford_refine_ls_R_factor_ref 0.0698 _refine_ls_wR_factor_ref 0.0886 _refine_ls_goodness_of_fit_ref 1.3471 _refine_ls_shift/su_max 0.000177 # The values computed from all data _oxford_reflns_number_all 4409 _refine_ls_R_factor_all 0.1645 _refine_ls_wR_factor_all 0.0991 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2367 _refine_ls_R_factor_gt 0.0698 _refine_ls_wR_factor_gt 0.0886 # 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 . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # 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: 10.2 -1.95 5.80 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487--?. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351--359. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Sheldrick, G. M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens I1 I 0.16925(13) 0.70029(11) 0.29087(8) 0.0453 1.0000 Uani . . . . . . . I2 I 0.08128(12) 0.35960(10) 0.45300(8) 0.0366 1.0000 Uani . . . . . . . O3 O 0.0262(11) 0.1993(9) 0.3889(7) 0.0437 1.0000 Uani . . . . . . . O4 O 0.0866(12) 0.2379(10) 0.5599(7) 0.0458 1.0000 Uani . . . . . . . O5 O 0.0947(14) 0.8432(11) 0.2047(9) 0.0673 1.0000 Uani . . . . . . . N6 N 0.5635(14) 0.7300(13) 0.2762(9) 0.0415 1.0000 Uani . . . . . . . O7 O 0.0491(14) 0.5753(11) 0.2834(8) 0.0562 1.0000 Uani . . . . . . . O8 O 0.4114(12) 0.8026(10) 0.2967(7) 0.0506 1.0000 Uani . . . . . . . O9 O 0.1735(14) 0.4908(11) 0.4700(8) 0.0446 1.0000 Uani . . . . . . . N10 N 0.1662(14) 0.1123(13) 0.3635(9) 0.0471 1.0000 Uani . . . . . . . C11 C 0.620(2) 0.9247(16) 0.1391(12) 0.0604 1.0000 Uani . . . . . . . C12 C 0.3213(19) 0.1627(14) 0.3664(11) 0.0385 1.0000 Uani . . . . . . . C13 C 0.546(2) 0.6388(17) 0.2236(13) 0.0477 1.0000 Uani . . . . . . . C14 C 0.387(2) 0.6167(18) 0.2204(11) 0.0487 1.0000 Uani . . . . . . . C15 C 0.4570(19) 0.3175(16) 0.4045(10) 0.0393 1.0000 Uani . . . . . . . C16 C 0.177(2) -0.0292(14) 0.4312(12) 0.0624 1.0000 Uani . . . . . . . C17 C 0.6766(19) 0.8316(16) 0.2241(11) 0.0509 1.0000 Uani . . . . . . . C18 C 0.612(2) 0.2553(18) 0.3731(12) 0.0561 1.0000 Uani . . . . . . . C19 C 0.3108(18) 0.2697(15) 0.3966(10) 0.0321 1.0000 Uani . . . . . . . C20 C 0.682(2) 0.573(2) 0.1852(14) 0.0714 1.0000 Uani . . . . . . . C21 C 0.142(2) 0.233(2) 0.2027(12) 0.0713 1.0000 Uani . . . . . . . C22 C 0.662(2) 0.490(2) 0.1374(14) 0.0752 1.0000 Uani . . . . . . . C23 C 0.621(2) 0.144(2) 0.3452(12) 0.0675 1.0000 Uani . . . . . . . C24 C 0.364(3) 0.5299(18) 0.1758(13) 0.0637 1.0000 Uani . . . . . . . C25 C 0.635(2) 0.6496(16) 0.3611(11) 0.0620 1.0000 Uani . . . . . . . C26 C 0.144(2) 0.1000(18) 0.2748(12) 0.0580 1.0000 Uani . . . . . . . C27 C 0.505(3) 0.4674(19) 0.1333(14) 0.0775 1.0000 Uani . . . . . . . C28 C 0.479(2) 0.0989(19) 0.3370(12) 0.0633 1.0000 Uani . . . . . . . C29 C 0.098(4) 0.218(3) 0.1206(19) 0.1500 1.0000 Uani D . . . . . . C30 C 0.676(4) 1.140(3) 0.0211(18) 0.1676 1.0000 Uani . . . . . . . C31 C 0.720(3) 1.038(3) 0.1014(18) 0.1235 1.0000 Uani . . . . . . . C32 C 0.110(4) 0.306(4) 0.037(2) 0.2571 1.0000 Uani D . . . . . . H111 H 0.5047 0.9659 0.1489 0.0800 1.0000 Uiso R . . . . . . H112 H 0.6282 0.8731 0.0972 0.0800 1.0000 Uiso R . . . . . . H151 H 0.4496 0.3889 0.4284 0.0521 1.0000 Uiso R . . . . . . H161 H 0.2792 -0.0856 0.4173 0.0911 1.0000 Uiso R . . . . . . H162 H 0.1783 -0.0201 0.4896 0.0910 1.0000 Uiso R . . . . . . H163 H 0.0830 -0.0692 0.4294 0.0910 1.0000 Uiso R . . . . . . H171 H 0.6864 0.8866 0.2616 0.0660 1.0000 Uiso R . . . . . . H172 H 0.7863 0.7808 0.2122 0.0660 1.0000 Uiso R . . . . . . H181 H 0.7090 0.2884 0.3735 0.0611 1.0000 Uiso R . . . . . . H201 H 0.7890 0.5859 0.1901 0.0860 1.0000 Uiso R . . . . . . H211 H 0.0588 0.3026 0.2198 0.0840 1.0000 Uiso R . . . . . . H212 H 0.2517 0.2588 0.1933 0.0841 1.0000 Uiso R . . . . . . H221 H 0.7534 0.4429 0.1116 0.0931 1.0000 Uiso R . . . . . . H231 H 0.7256 0.1012 0.3280 0.0759 1.0000 Uiso R . . . . . . H241 H 0.2582 0.5093 0.1761 0.0810 1.0000 Uiso R . . . . . . H251 H 0.7363 0.5911 0.3488 0.0871 1.0000 Uiso R . . . . . . H252 H 0.6609 0.7109 0.3892 0.0870 1.0000 Uiso R . . . . . . H253 H 0.5577 0.5958 0.4002 0.0870 1.0000 Uiso R . . . . . . H261 H 0.2362 0.0348 0.2596 0.0880 1.0000 Uiso R . . . . . . H262 H 0.0393 0.0691 0.2773 0.0881 1.0000 Uiso R . . . . . . H271 H 0.4896 0.4165 0.0974 0.0860 1.0000 Uiso R . . . . . . H281 H 0.4840 0.0265 0.3142 0.0771 1.0000 Uiso R . . . . . . H301 H 0.7619 1.1944 -0.0034 0.2260 1.0000 Uiso R . . . . . . H302 H 0.5732 1.1970 0.0330 0.2260 1.0000 Uiso R . . . . . . H303 H 0.6595 1.0952 -0.0206 0.2260 1.0000 Uiso R . . . . . . H311 H 0.7146 1.0839 0.1462 0.1340 1.0000 Uiso R . . . . . . H312 H 0.8337 0.9939 0.0909 0.1340 1.0000 Uiso R . . . . . . H291 H -0.0168 0.2029 0.1308 0.2021 1.0000 Uiso R . . . . . . H292 H 0.1719 0.1359 0.1133 0.2021 1.0000 Uiso R . . . . . . H321 H 0.0789 0.2799 -0.0103 0.2462 1.0000 Uiso R . . . . . . H322 H 0.0370 0.3882 0.0420 0.2462 1.0000 Uiso R . . . . . . H323 H 0.2238 0.3219 0.0247 0.2462 1.0000 Uiso R . . . . . . 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 I1 0.0353(9) 0.0446(10) 0.0605(11) -0.0205(8) 0.0042(8) -0.0145(7) I2 0.0352(8) 0.0316(8) 0.0464(10) -0.0157(7) -0.0001(7) -0.0088(7) O3 0.018(5) 0.041(7) 0.073(9) -0.026(6) 0.017(6) -0.007(5) O4 0.034(6) 0.060(7) 0.053(8) -0.030(6) 0.007(5) -0.014(5) O5 0.054(8) 0.037(7) 0.099(11) -0.002(7) 0.005(8) -0.019(6) N6 0.023(7) 0.046(8) 0.056(10) -0.022(8) 0.005(7) -0.004(6) O7 0.056(8) 0.048(8) 0.076(9) -0.029(7) 0.002(7) -0.021(6) O8 0.034(6) 0.045(6) 0.083(9) -0.038(6) 0.004(6) -0.007(5) O9 0.042(7) 0.036(7) 0.064(9) -0.030(6) 0.001(6) -0.006(5) N10 0.029(7) 0.050(9) 0.065(10) -0.027(8) 0.012(7) -0.008(6) C11 0.053(11) 0.047(11) 0.059(13) 0.009(10) 0.005(10) -0.006(9) C12 0.042(10) 0.022(8) 0.049(11) -0.011(8) 0.000(8) -0.002(7) C13 0.037(11) 0.040(10) 0.063(13) -0.009(10) -0.001(9) -0.014(8) C14 0.063(13) 0.056(12) 0.034(11) -0.018(10) 0.013(9) -0.030(10) C15 0.036(10) 0.039(10) 0.036(11) 0.004(8) 0.001(8) -0.017(8) C16 0.053(11) 0.024(9) 0.094(15) -0.002(10) 0.014(10) -0.007(8) C17 0.050(10) 0.046(10) 0.058(13) -0.016(10) 0.016(9) -0.024(9) C18 0.045(11) 0.054(11) 0.072(14) -0.011(10) 0.000(10) -0.029(9) C19 0.033(9) 0.046(10) 0.026(9) -0.021(8) 0.012(7) -0.017(8) C20 0.048(12) 0.076(15) 0.105(18) -0.049(14) 0.009(12) -0.018(11) C21 0.081(14) 0.090(16) 0.044(13) -0.015(12) -0.016(11) -0.017(12) C22 0.036(11) 0.077(14) 0.117(19) -0.044(14) 0.025(11) -0.015(10) C23 0.028(10) 0.107(17) 0.066(14) -0.018(13) -0.013(9) -0.013(10) C24 0.075(14) 0.055(12) 0.072(15) -0.025(11) -0.003(12) -0.026(11) C25 0.080(13) 0.048(11) 0.056(13) -0.004(10) -0.021(11) -0.016(10) C26 0.054(12) 0.067(13) 0.065(14) -0.044(11) 0.018(10) -0.015(9) C27 0.084(15) 0.079(15) 0.095(17) -0.063(13) 0.033(13) -0.038(12) C28 0.053(12) 0.073(13) 0.080(15) -0.055(12) -0.006(11) 0.005(10) C29 0.15(3) 0.19(3) 0.09(2) 0.03(2) 0.00(2) -0.10(2) C30 0.25(4) 0.12(2) 0.11(2) 0.06(2) -0.02(2) -0.12(3) C31 0.11(2) 0.10(2) 0.13(2) 0.007(19) 0.026(18) -0.033(17) C32 0.09(3) 0.54(8) 0.12(3) -0.04(4) -0.01(2) -0.12(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.17390(11) 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 I1 . O5 . 1.745(12) yes I1 . O7 . 1.836(10) yes I1 . O8 . 2.466(9) yes I1 . C14 . 2.149(18) yes I2 . O9 2_566 2.732(10) yes I2 . O3 . 2.366(10) yes I2 . O4 . 1.771(11) yes I2 . O9 . 1.807(10) yes I2 . C19 . 2.135(14) yes O3 . N10 . 1.407(14) yes N6 . O8 . 1.374(14) yes N6 . C13 . 1.49(2) yes N6 . C17 . 1.524(17) yes N6 . C25 . 1.469(19) yes N10 . C12 . 1.484(18) yes N10 . C16 . 1.528(18) yes N10 . C26 . 1.490(19) yes C11 . C17 . 1.46(2) yes C11 . C31 . 1.50(2) yes C11 . H111 . 0.969 no C11 . H112 . 0.970 no C12 . C19 . 1.337(18) yes C12 . C28 . 1.41(2) yes C13 . C14 . 1.38(2) yes C13 . C20 . 1.36(2) yes C14 . C24 . 1.37(2) yes C15 . C18 . 1.40(2) yes C15 . C19 . 1.424(19) yes C15 . H151 . 0.930 no C16 . H161 . 0.961 no C16 . H162 . 0.961 no C16 . H163 . 0.960 no C17 . H171 . 0.972 no C17 . H172 . 0.971 no C18 . C23 . 1.36(2) yes C18 . H181 . 0.932 no C20 . C22 . 1.37(2) yes C20 . H201 . 0.930 no C21 . C26 . 1.50(2) yes C21 . C29 . 1.46(3) yes C21 . H211 . 0.972 no C21 . H212 . 0.972 no C22 . C27 . 1.37(2) yes C22 . H221 . 0.929 no C23 . C28 . 1.38(2) yes C23 . H231 . 0.932 no C24 . C27 . 1.40(2) yes C24 . H241 . 0.931 no C25 . H251 . 0.961 no C25 . H252 . 0.960 no C25 . H253 . 0.961 no C26 . H261 . 0.969 no C26 . H262 . 0.969 no C27 . H271 . 0.930 no C28 . H281 . 0.931 no C29 . C32 . 1.361(17) yes C29 . H291 . 0.970 no C29 . H292 . 0.970 no C30 . C31 . 1.41(3) yes C30 . H301 . 0.961 no C30 . H302 . 0.960 no C30 . H303 . 0.961 no C31 . H311 . 0.970 no C31 . H312 . 0.970 no C32 . H321 . 0.960 no C32 . H322 . 0.960 no C32 . H323 . 0.960 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 O5 . I1 . O7 . 101.7(5) yes O5 . I1 . O8 . 90.5(5) yes O7 . I1 . O8 . 159.9(4) yes O5 . I1 . C14 . 99.3(6) yes O7 . I1 . C14 . 92.2(6) yes O8 . I1 . C14 . 69.8(5) yes O9 2_566 I2 . O3 . 120.8(3) yes O9 2_566 I2 . O4 . 85.2(4) yes O3 . I2 . O4 . 91.1(4) yes O9 2_566 I2 . O9 . 74.8(5) yes O3 . I2 . O9 . 160.8(4) yes O4 . I2 . O9 . 101.9(5) yes O9 2_566 I2 . C19 . 168.3(4) yes O3 . I2 . C19 . 70.8(4) yes O4 . I2 . C19 . 96.8(5) yes O9 . I2 . C19 . 93.5(5) yes I2 . O3 . N10 . 116.6(7) yes O8 . N6 . C13 . 111.9(11) yes O8 . N6 . C17 . 107.8(11) yes C13 . N6 . C17 . 110.6(12) yes O8 . N6 . C25 . 107.0(12) yes C13 . N6 . C25 . 110.4(12) yes C17 . N6 . C25 . 109.0(12) yes N6 . O8 . I1 . 113.9(7) yes I2 . O9 . I2 2_566 105.2(5) yes O3 . N10 . C12 . 109.3(10) yes O3 . N10 . C16 . 109.1(11) yes C12 . N10 . C16 . 106.9(12) yes O3 . N10 . C26 . 109.3(12) yes C12 . N10 . C26 . 114.0(12) yes C16 . N10 . C26 . 108.1(13) yes C17 . C11 . C31 . 112.6(17) yes C17 . C11 . H111 . 108.4 no C31 . C11 . H111 . 107.3 no C17 . C11 . H112 . 108.7 no C31 . C11 . H112 . 110.0 no H111 . C11 . H112 . 109.7 no N10 . C12 . C19 . 119.4(13) yes N10 . C12 . C28 . 120.3(13) yes C19 . C12 . C28 . 120.3(15) yes N6 . C13 . C14 . 117.2(15) yes N6 . C13 . C20 . 121.7(15) yes C14 . C13 . C20 . 121.0(17) yes I1 . C14 . C13 . 123.2(13) yes I1 . C14 . C24 . 116.7(13) yes C13 . C14 . C24 . 119.9(18) yes C18 . C15 . C19 . 117.7(15) yes C18 . C15 . H151 . 121.2 no C19 . C15 . H151 . 121.1 no N10 . C16 . H161 . 108.9 no N10 . C16 . H162 . 108.3 no H161 . C16 . H162 . 109.9 no N10 . C16 . H163 . 110.4 no H161 . C16 . H163 . 109.6 no H162 . C16 . H163 . 109.7 no N6 . C17 . C11 . 116.4(13) yes N6 . C17 . H171 . 107.5 no C11 . C17 . H171 . 107.4 no N6 . C17 . H172 . 108.2 no C11 . C17 . H172 . 107.8 no H171 . C17 . H172 . 109.5 no C15 . C18 . C23 . 119.9(15) yes C15 . C18 . H181 . 119.7 no C23 . C18 . H181 . 120.3 no C15 . C19 . I2 . 115.8(11) yes C15 . C19 . C12 . 121.3(14) yes I2 . C19 . C12 . 122.3(11) yes C13 . C20 . C22 . 120.3(18) yes C13 . C20 . H201 . 120.1 no C22 . C20 . H201 . 119.6 no C26 . C21 . C29 . 109.1(18) yes C26 . C21 . H211 . 109.5 no C29 . C21 . H211 . 109.3 no C26 . C21 . H212 . 109.8 no C29 . C21 . H212 . 109.7 no H211 . C21 . H212 . 109.4 no C20 . C22 . C27 . 119.3(17) yes C20 . C22 . H221 . 121.6 no C27 . C22 . H221 . 118.9 no C18 . C23 . C28 . 121.8(17) yes C18 . C23 . H231 . 118.6 no C28 . C23 . H231 . 119.5 no C14 . C24 . C27 . 118.2(18) yes C14 . C24 . H241 . 121.0 no C27 . C24 . H241 . 120.7 no N6 . C25 . H251 . 108.6 no N6 . C25 . H252 . 108.5 no H251 . C25 . H252 . 109.3 no N6 . C25 . H253 . 111.3 no H251 . C25 . H253 . 109.8 no H252 . C25 . H253 . 109.3 no C21 . C26 . N10 . 112.1(14) yes C21 . C26 . H261 . 108.0 no N10 . C26 . H261 . 109.1 no C21 . C26 . H262 . 108.6 no N10 . C26 . H262 . 109.6 no H261 . C26 . H262 . 109.5 no C24 . C27 . C22 . 121.2(18) yes C24 . C27 . H271 . 119.1 no C22 . C27 . H271 . 119.5 no C12 . C28 . C23 . 118.5(16) yes C12 . C28 . H281 . 119.6 no C23 . C28 . H281 . 121.9 no C21 . C29 . C32 . 127(3) yes C21 . C29 . H291 . 106.8 no C32 . C29 . H291 . 105.3 no C21 . C29 . H292 . 105.4 no C32 . C29 . H292 . 102.0 no H291 . C29 . H292 . 109.5 no C31 . C30 . H301 . 111.9 no C31 . C30 . H302 . 108.5 no H301 . C30 . H302 . 109.5 no C31 . C30 . H303 . 107.7 no H301 . C30 . H303 . 109.6 no H302 . C30 . H303 . 109.6 no C11 . C31 . C30 . 120(2) yes C11 . C31 . H311 . 107.9 no C30 . C31 . H311 . 106.9 no C11 . C31 . H312 . 105.5 no C30 . C31 . H312 . 107.0 no H311 . C31 . H312 . 109.9 no C29 . C32 . H321 . 116.7 no C29 . C32 . H322 . 104.1 no H321 . C32 . H322 . 109.5 no C29 . C32 . H323 . 107.4 no H321 . C32 . H323 . 109.5 no H322 . C32 . H323 . 109.5 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 C16 . H161 . O8 1_545 140 0.96 2.56 3.35(3) yes C16 . H163 . O4 2_556 161 0.96 2.42 3.34(3) yes C18 . H181 . O3 1_655 139 0.93 2.59 3.35(3) yes C25 . H252 . O4 2_666 139 0.96 2.53 3.31(3) yes C26 . H261 . O8 1_545 150 0.97 2.50 3.37(3) yes