# 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, 2007 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _audit_creation_date 07-11-09 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title 'scale in P 21/c' _chemical_name_systematic ? _chemical_melting_point ? #looking for refcif # 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_author_name 'Jens Hasserodt' _publ_contact_author_address ; \'Ecole Normale Sup\'erieure de Lyon 46, All\'ee d'Italie Lyon Cedex 07 F-69364 FRANCE ; _publ_contact_author_email JENS.HASSERODT@ENS-LYON.FR _publ_section_title ; Significant relaxivity gap between a low-spin and a high-spin iron(II) complex of structural similarity : an attractive off/on system for the potential design of responsive MRI probes ; #_publ_section_related_literature #; #? #; #_publ_section_comment #; #? #; #_publ_section_acknowledgements #; #? #; _publ_section_figure_captions ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; loop_ _publ_author_name 'Vitalie Stavila' 'Mustapha Allali' 'Laurence Canaple' 'Yvon Stortz' "C\'ecile Franc" 'Philippe Maurin' 'Olivier Beuf' ; O.Dufay ; 'Jacques Samarut' 'Marc Janier' 'Jens Hasserodt' data_1 _database_code_depnum_ccdc_archive 'CCDC 662473' _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 ; ? ; # 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 7.90480(70) _cell_length_b 10.05630(110) _cell_length_c 25.40560(250) _cell_angle_alpha 90.0000 _cell_angle_beta 95.4398(54) _cell_angle_gamma 90.0000 _cell_volume 2010.473(345) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C22.50 H28.75 Br1 Cl0.50 N6.25 O1 # Dc = 1.65 Fooo = 784.00 Mu = 21.43 M = 500.40 # Found Formula = C18 H28 Cl1 N5 O1 # Dc = 1.21 FOOO = 784.00 Mu = 2.06 M = 365.91 _chemical_formula_sum 'C18 H28 Cl1 N5 O1' _chemical_formula_moiety 'C18 H26 N5, H2 O, Cl' _chemical_compound_source ? _chemical_formula_weight 365.91 _cell_measurement_reflns_used 1493 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.878 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.07 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.206 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_T_max . # 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 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _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 293 _diffrn_reflns_number 4819 _reflns_number_total 3452 _diffrn_reflns_av_R_equivalents 0.042 # Number of reflections with Friedels Law is 3452 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4878 _diffrn_reflns_theta_min 1.610 _diffrn_reflns_theta_max 28.071 _diffrn_measured_fraction_theta_max 0.706 _diffrn_reflns_theta_full 25.264 _diffrn_measured_fraction_theta_full 0.759 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 33 _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 -0.21 _refine_diff_density_max 0.24 # 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>1.0\s(I) _refine_ls_number_reflns 1915 _refine_ls_number_restraints 0 _refine_ls_number_parameters 227 _oxford_refine_ls_R_factor_ref 0.0742 _refine_ls_wR_factor_ref 0.0789 _refine_ls_goodness_of_fit_ref 1.0655 _refine_ls_shift/su_max 0.000253 # The values computed from all data _oxford_reflns_number_all 3438 _refine_ls_R_factor_all 0.1399 _refine_ls_wR_factor_all 0.1380 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1443 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_gt 0.0663 # 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 F _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= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 0.03P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Grazia, A., Moliterni, G., Polidori, G. & Spagna, R. (1999). J. App. Cryst. 32, 115-119. 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. 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 N2 N 0.8412(4) 0.8744(3) 0.60268(15) 0.0634 1.0000 Uani . . . . . . . N3 N 1.1567(4) 0.9606(4) 0.58496(15) 0.0699 1.0000 Uani . . . . . . . N4 N 1.0031(5) 0.6660(3) 0.66622(15) 0.0695 1.0000 Uani . . . . . . . N5 N 1.0208(4) 0.6876(3) 0.55561(15) 0.0679 1.0000 Uani . . . . . . . C7 C 0.7478(5) 0.8040(4) 0.63929(19) 0.0720 1.0000 Uani . . . . . . . C8 C 0.7908(6) 0.8522(5) 0.5473(2) 0.0818 1.0000 Uani . . . . . . . N9 N 1.2391(6) 0.7309(5) 0.78885(18) 0.0908 1.0000 Uani . . . . . . . C10 C 1.0617(6) 1.0487(4) 0.60805(19) 0.0663 1.0000 Uani . . . . . . . C11 C 0.8468(6) 0.7174(5) 0.53026(19) 0.0772 1.0000 Uani . . . . . . . C12 C 0.8632(6) 0.7416(5) 0.68455(19) 0.0790 1.0000 Uani . . . . . . . C13 C 0.8840(5) 1.0107(4) 0.6167(2) 0.0791 1.0000 Uani . . . . . . . C14 C 0.9491(6) 0.5537(4) 0.6313(2) 0.0773 1.0000 Uani . . . . . . . C15 C 1.1215(7) 1.1729(5) 0.6230(3) 0.0988 1.0000 Uani . . . . . . . C16 C 1.2248(6) 0.7328(5) 0.7369(2) 0.0804 1.0000 Uani . . . . . . . C17 C 1.3017(8) 0.8289(6) 0.7095(2) 0.0978 1.0000 Uani . . . . . . . C18 C 1.0426(6) 0.5571(4) 0.5828(2) 0.0759 1.0000 Uani . . . . . . . C19 C 1.3303(8) 0.8270(7) 0.8140(2) 0.0972 1.0000 Uani . . . . . . . C20 C 1.1235(7) 0.6210(5) 0.7101(2) 0.0974 1.0000 Uani . . . . . . . C21 C 1.4086(7) 0.9272(6) 0.7902(3) 0.0939 1.0000 Uani . . . . . . . C22 C 1.3142(6) 0.9981(6) 0.5769(2) 0.0848 1.0000 Uani . . . . . . . C23 C 1.3820(7) 1.1182(7) 0.5907(3) 0.1061 1.0000 Uani . . . . . . . C24 C 1.2836(9) 1.2080(6) 0.6141(3) 0.1223 1.0000 Uani . . . . . . . C25 C 1.3931(7) 0.9280(6) 0.7364(3) 0.1006 1.0000 Uani . . . . . . . Cl1 Cl 0.29003(15) 0.68849(12) 0.47530(5) 0.0863 1.0000 Uani . . . . . . . O2 O 0.4830(4) 0.5316(4) 0.57587(14) 0.0974 1.0000 Uani . . . . . . . H71 H 0.6731 0.8660 0.6548 0.0886 1.0000 Uiso R . . . . . . H72 H 0.6772 0.7357 0.6198 0.0888 1.0000 Uiso R . . . . . . H81 H 0.6694 0.8609 0.5402 0.0977 1.0000 Uiso R . . . . . . H82 H 0.8450 0.9190 0.5267 0.0978 1.0000 Uiso R . . . . . . H111 H 0.7702 0.6520 0.5422 0.0929 1.0000 Uiso R . . . . . . H112 H 0.8479 0.7155 0.4923 0.0926 1.0000 Uiso R . . . . . . H121 H 0.7981 0.6835 0.7051 0.0982 1.0000 Uiso R . . . . . . H122 H 0.9081 0.8140 0.7069 0.0975 1.0000 Uiso R . . . . . . H131 H 0.8718 1.0226 0.6540 0.0948 1.0000 Uiso R . . . . . . H132 H 0.8060 1.0707 0.5970 0.0949 1.0000 Uiso R . . . . . . H141 H 0.9709 0.4695 0.6488 0.0939 1.0000 Uiso R . . . . . . H142 H 0.8282 0.5627 0.6205 0.0940 1.0000 Uiso R . . . . . . H151 H 1.0530 1.2319 0.6389 0.1161 1.0000 Uiso R . . . . . . H171 H 1.2918 0.8267 0.6726 0.1151 1.0000 Uiso R . . . . . . H181 H 1.1620 0.5443 0.5930 0.0948 1.0000 Uiso R . . . . . . H182 H 1.0009 0.4868 0.5593 0.0952 1.0000 Uiso R . . . . . . H191 H 1.3395 0.8250 0.8509 0.1140 1.0000 Uiso R . . . . . . H201 H 1.0632 0.5737 0.7357 0.1167 1.0000 Uiso R . . . . . . H202 H 1.2030 0.5611 0.6952 0.1170 1.0000 Uiso R . . . . . . H211 H 1.4674 0.9940 0.8099 0.1109 1.0000 Uiso R . . . . . . H221 H 1.3804 0.9367 0.5607 0.1003 1.0000 Uiso R . . . . . . H231 H 1.4917 1.1387 0.5836 0.1269 1.0000 Uiso R . . . . . . H241 H 1.3254 1.2931 0.6232 0.1418 1.0000 Uiso R . . . . . . H251 H 1.4426 0.9951 0.7179 0.1188 1.0000 Uiso R . . . . . . H3 H 0.5395 0.4709 0.5643 0.1430 1.0000 Uiso R . . . . . . H10 H 0.4553 0.5919 0.5551 0.1431 1.0000 Uiso R . . . . . . H252 H 1.0975 0.6992 0.5327 0.1024 1.0000 Uiso R . . . . . . H1 H 1.0520 0.7512 0.5782 0.1019 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 N2 0.0606(19) 0.065(2) 0.067(3) -0.0058(18) 0.0214(19) -0.0013(17) N3 0.065(2) 0.073(2) 0.073(3) 0.005(2) 0.014(2) -0.0040(19) N4 0.081(2) 0.065(2) 0.063(2) -0.0026(18) 0.009(2) -0.0001(19) N5 0.069(2) 0.071(2) 0.069(2) -0.0140(19) 0.0296(19) -0.0067(18) C7 0.063(3) 0.080(3) 0.077(3) -0.011(3) 0.024(2) -0.002(2) C8 0.066(3) 0.102(4) 0.077(4) -0.004(3) 0.005(3) 0.009(3) N9 0.088(3) 0.116(4) 0.068(3) 0.017(3) 0.002(3) 0.016(3) C10 0.070(3) 0.053(3) 0.075(3) 0.005(2) 0.002(3) 0.004(2) C11 0.075(3) 0.099(4) 0.059(3) -0.009(2) 0.011(3) -0.004(3) C12 0.093(3) 0.082(3) 0.067(3) -0.006(3) 0.035(3) -0.009(3) C13 0.075(3) 0.069(3) 0.096(4) -0.007(3) 0.027(3) 0.005(2) C14 0.087(3) 0.063(3) 0.086(4) 0.003(3) 0.027(3) -0.007(2) C15 0.078(3) 0.072(4) 0.143(5) -0.006(3) -0.007(4) 0.001(3) C16 0.082(3) 0.091(4) 0.067(4) 0.018(3) 0.001(3) 0.008(3) C17 0.120(4) 0.114(5) 0.058(3) 0.010(3) 0.005(3) -0.010(4) C18 0.080(3) 0.058(3) 0.093(4) -0.010(2) 0.023(3) -0.003(2) C19 0.085(4) 0.140(5) 0.065(4) 0.009(4) 0.001(3) 0.024(4) C20 0.117(4) 0.086(4) 0.087(4) 0.020(3) -0.001(3) 0.005(3) C21 0.079(3) 0.117(5) 0.084(4) -0.018(4) -0.003(3) 0.014(3) C22 0.066(3) 0.099(4) 0.090(4) 0.010(3) 0.011(3) -0.004(3) C23 0.069(3) 0.111(5) 0.135(6) 0.036(4) -0.006(4) -0.022(4) C24 0.094(4) 0.081(4) 0.184(8) 0.009(4) -0.023(5) -0.018(4) C25 0.098(4) 0.112(5) 0.093(5) 0.009(4) 0.012(4) -0.012(3) Cl1 0.0842(8) 0.0918(9) 0.0882(10) 0.0132(7) 0.0367(7) 0.0095(6) O2 0.091(2) 0.119(3) 0.082(2) -0.006(2) 0.012(2) 0.009(2) _refine_ls_extinction_coef 240(60) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.545(2) 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 N2 . C7 . 1.429(5) yes N2 . C8 . 1.444(5) yes N2 . C13 . 1.448(5) yes N3 . C10 . 1.332(6) yes N3 . C22 . 1.335(6) yes N4 . C12 . 1.454(6) yes N4 . C14 . 1.474(5) yes N4 . C20 . 1.467(5) yes N5 . C11 . 1.493(5) yes N5 . C18 . 1.486(5) yes N5 . H252 . 0.886 no N5 . H1 . 0.878 no C7 . C12 . 1.533(6) yes C7 . H71 . 0.968 no C7 . H72 . 0.988 no C8 . C11 . 1.503(6) yes C8 . H81 . 0.964 no C8 . H82 . 0.974 no N9 . C16 . 1.315(6) yes N9 . C19 . 1.332(7) yes C10 . C13 . 1.492(6) yes C10 . C15 . 1.377(6) yes C11 . H111 . 0.963 no C11 . H112 . 0.966 no C12 . H121 . 0.964 no C12 . H122 . 0.969 no C13 . H131 . 0.970 no C13 . H132 . 0.967 no C14 . C18 . 1.496(6) yes C14 . H141 . 0.964 no C14 . H142 . 0.974 no C15 . C24 . 1.369(8) yes C15 . H151 . 0.921 no C16 . C17 . 1.367(7) yes C16 . C20 . 1.504(7) yes C17 . C25 . 1.375(7) yes C17 . H171 . 0.934 no C18 . H181 . 0.963 no C18 . H182 . 0.964 no C19 . C21 . 1.355(8) yes C19 . H191 . 0.934 no C20 . H201 . 0.967 no C20 . H202 . 0.973 no C21 . C25 . 1.360(8) yes C21 . H211 . 0.934 no C22 . C23 . 1.355(7) yes C22 . H221 . 0.930 no C23 . C24 . 1.365(8) yes C23 . H231 . 0.926 no C24 . H241 . 0.938 no C25 . H251 . 0.929 no O2 . H3 . 0.827 no O2 . H10 . 0.820 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 C7 . N2 . C8 . 116.5(4) yes C7 . N2 . C13 . 115.6(4) yes C8 . N2 . C13 . 115.0(4) yes C10 . N3 . C22 . 116.9(4) yes C12 . N4 . C14 . 114.1(4) yes C12 . N4 . C20 . 112.1(4) yes C14 . N4 . C20 . 110.5(4) yes C11 . N5 . C18 . 116.1(3) yes C11 . N5 . H252 . 110.5 no C18 . N5 . H252 . 111.5 no C11 . N5 . H1 . 109.0 no C18 . N5 . H1 . 109.1 no H252 . N5 . H1 . 99.5 no N2 . C7 . C12 . 112.5(3) yes N2 . C7 . H71 . 108.6 no C12 . C7 . H71 . 107.5 no N2 . C7 . H72 . 108.6 no C12 . C7 . H72 . 111.1 no H71 . C7 . H72 . 108.4 no N2 . C8 . C11 . 111.0(4) yes N2 . C8 . H81 . 110.2 no C11 . C8 . H81 . 110.1 no N2 . C8 . H82 . 108.7 no C11 . C8 . H82 . 108.2 no H81 . C8 . H82 . 108.6 no C16 . N9 . C19 . 117.6(5) yes N3 . C10 . C13 . 118.2(4) yes N3 . C10 . C15 . 122.1(5) yes C13 . C10 . C15 . 119.7(5) yes C8 . C11 . N5 . 110.0(3) yes C8 . C11 . H111 . 108.3 no N5 . C11 . H111 . 108.0 no C8 . C11 . H112 . 109.6 no N5 . C11 . H112 . 109.4 no H111 . C11 . H112 . 111.6 no C7 . C12 . N4 . 113.0(4) yes C7 . C12 . H121 . 110.1 no N4 . C12 . H121 . 108.6 no C7 . C12 . H122 . 106.9 no N4 . C12 . H122 . 109.5 no H121 . C12 . H122 . 108.8 no C10 . C13 . N2 . 114.0(4) yes C10 . C13 . H131 . 107.1 no N2 . C13 . H131 . 108.3 no C10 . C13 . H132 . 109.1 no N2 . C13 . H132 . 109.9 no H131 . C13 . H132 . 108.1 no N4 . C14 . C18 . 109.9(4) yes N4 . C14 . H141 . 111.5 no C18 . C14 . H141 . 108.6 no N4 . C14 . H142 . 108.6 no C18 . C14 . H142 . 108.2 no H141 . C14 . H142 . 109.8 no C10 . C15 . C24 . 119.4(6) yes C10 . C15 . H151 . 120.3 no C24 . C15 . H151 . 120.3 no N9 . C16 . C17 . 121.4(5) yes N9 . C16 . C20 . 115.8(5) yes C17 . C16 . C20 . 122.8(5) yes C16 . C17 . C25 . 119.9(5) yes C16 . C17 . H171 . 119.7 no C25 . C17 . H171 . 120.5 no C14 . C18 . N5 . 111.1(4) yes C14 . C18 . H181 . 109.0 no N5 . C18 . H181 . 108.1 no C14 . C18 . H182 . 109.2 no N5 . C18 . H182 . 109.9 no H181 . C18 . H182 . 109.6 no N9 . C19 . C21 . 125.1(6) yes N9 . C19 . H191 . 117.0 no C21 . C19 . H191 . 118.0 no C16 . C20 . N4 . 113.1(4) yes C16 . C20 . H201 . 109.8 no N4 . C20 . H201 . 109.7 no C16 . C20 . H202 . 107.6 no N4 . C20 . H202 . 107.0 no H201 . C20 . H202 . 109.5 no C19 . C21 . C25 . 116.9(6) yes C19 . C21 . H211 . 121.4 no C25 . C21 . H211 . 121.7 no N3 . C22 . C23 . 124.3(5) yes N3 . C22 . H221 . 117.0 no C23 . C22 . H221 . 118.7 no C22 . C23 . C24 . 118.4(5) yes C22 . C23 . H231 . 120.2 no C24 . C23 . H231 . 121.4 no C15 . C24 . C23 . 118.9(6) yes C15 . C24 . H241 . 120.6 no C23 . C24 . H241 . 120.6 no C17 . C25 . C21 . 119.2(6) yes C17 . C25 . H251 . 120.1 no C21 . C25 . H251 . 120.7 no H3 . O2 . H10 . 115.9 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 N5 . H1 . N3 . 144 0.88 2.26 3.016(8) yes