# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name _publ_author_address 'Ya-Jun Cheng' ; State Key Laboratory of Rare Earth Materials Chemistry and Applications & PKU-HKU Joint Laboratory in Rare Earth Materials and Bioinorganic Chemistry Peking University - Nonius B. V. Demo Lab For X-Ray Diffraction Department of Chemistry Peking University Beijing 100871 People's Republic of China ; 'Zhe-Ming Wang' ; State Key Laboratory of Rare Earth Materials Chemistry and Applications & PKU-HKU Joint Laboratory in Rare Earth Materials and Bioinorganic Chemistry Peking University - Nonius B. V. Demo Lab For X-Ray Diffraction Department of Chemistry Peking University Beijing 100871 People's Republic of China ; 'Chun-Sheng Liao' ; State Key Laboratory of Rare Earth Materials Chemistry and Applications & PKU-HKU Joint Laboratory in Rare Earth Materials and Bioinorganic Chemistry Peking University - Nonius B. V. Demo Lab For X-Ray Diffraction Department of Chemistry Peking University Beijing 100871 People's Republic of China ; 'Chun-Hua Yan' ; State Key Laboratory of Rare Earth Materials Chemistry and Applications & PKU-HKU Joint Laboratory in Rare Earth Materials and Bioinorganic Chemistry Peking University - Nonius B. V. Demo Lab For X-Ray Diffraction Department of Chemistry Peking University Beijing 100871 People's Republic of China ; _publ_contact_author_name 'Prof. Chun-Hua Yan' _publ_contact_author_address ; State Key Laboratory of Rare Earth Materials Chemistry and Applications & PKU-HKU Joint Laboratory in Rare Earth Materials and Bioinorganic Chemistry Peking University - Nonius B. V. Demo Lab For X-Ray Diffraction Department of Chemistry Peking University Beijing 100871 People's Republic of China ; _publ_contact_author_email chyan@chem.pku.edu.cn _publ_contact_author_phone '86-(10)-62754179' _publ_contact_author_fax '86-(10)-62754179' _publ_requested_journal 'New Journal of Chemistry' _publ_requested_category FO _publ_contact_letter ; ? ; # TITLE AND AUTHOR LIST _publ_section_title ; Novel sheet-like supramolecular architectures constructed from infinite hydrogen-bonded, protonated adenine-water-halide and polyiodide ribbons ; _publ_section_references ; Blessing, R. H. (1995). Acta Cryst. A51, 33-38. Blessing, R. H. (1997) J.Appl. Cryst. 30, 421-426. Mackay, S., Gilmore, C. J., Edwards, C., Tremayne, M., Stuart, N. & Shankland, K. (1998). "maXus: a computer program for the solution and refinement of crystal structures from diffraction data", University of Glasgow, Scotland, UK, Nonius BV, Delft, The Netherlands and MacScience Co. Ltd., Yokohama, Japan. Nonius B. V. (1998). "Collect" data collection software, Delft, The Netherlands. Otwinowski, Z. & Minor, M. (1997) " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, Carter,C. W. Jr. & Sweet, R.M. Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL Version 5.10. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1997). SHELXL97. PC Version. University of Goettingen, Germany. Sheldrick, G. M. (1997). SHELXS97. PC Version. University of Goettingen, Germany. ; data_1 _database_code_CSD 186872 _audit_creation_method SHELXL-97 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety [AdeH22+](Cl-)(I5-)(H2O) _chemical_formula_sum 'C5 H9 Cl I5 N5 O ' _chemical_formula_weight 825.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2477(2) _cell_length_b 10.7053(3) _cell_length_c 10.4233(3) _cell_angle_alpha 103.0848(11) _cell_angle_beta 91.7871(15) _cell_angle_gamma 100.8063(11) _cell_volume 877.91(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 27746 _cell_measurement_theta_min 3.51 _cell_measurement_theta_max 27.50 _exptl_crystal_description 'plate' _exptl_crystal_colour 'orange red' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.121 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 9.004 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.215 _exptl_absorpt_correction_T_max 0.279 _exptl_absorpt_process_details '(Blessing, 1995, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'NONIUS KappaCCD Diffractometer' _diffrn_measurement_method 'CCD' _diffrn_detector_area_resol_mean 0.76 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 27746 _diffrn_reflns_av_R_equivalents 0.0686 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3987 _reflns_number_gt 2778 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _publ_section_references ; collect: "Collect" data collection software, Nonius B.V., Delft, The Netherlands, 1998. HKL Scalepack & HKL Denzo: Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R.M. Sweet, Eds., Academic Press. absorption correction: R.H. Blessing (1995) Acta Cryst. A51, 33-37. R.H. Blessing (1997) J.Appl. Cryst. 30, 421-426. maXus: S.Mackay, C.J.Gilmore, C.Edwards, M. Tremayne, N. Stuart, K.Shankland maXus: a computer program for the solution and refinement of crystal structures from diffraction data", University of Glasgow, Scotland, UK, Nonius BV, Delft, The Netherlands and MacScience Co. Ltd., Yokohama, Japan (1998). Sheldrick, G. M. (1998). SHELXTL Version 5.1. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1997). SHELX-97. PC Version. University of Goettingen, Germany. ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+1.2892P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0060(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3987 _refine_ls_number_parameters 162 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0729 _refine_ls_wR_factor_gt 0.0653 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.27064(5) 0.46929(3) 0.64073(4) 0.05513(12) Uani 1 1 d . . . I2 I 0.37684(4) 0.23892(3) 0.47030(3) 0.04825(12) Uani 1 1 d . . . I3 I 0.49500(4) 0.02651(4) 0.30516(4) 0.05339(12) Uani 1 1 d . . . I4 I 0.42381(5) 0.18037(4) 0.06073(4) 0.05933(13) Uani 1 1 d . . . I5 I 0.35580(4) 0.31816(4) -0.12112(4) 0.05529(12) Uani 1 1 d . . . Cl1 Cl 0.05423(18) 0.75994(14) 0.81788(13) 0.0561(4) Uani 1 1 d . . . N1 N 0.0812(5) 0.8310(4) 0.1141(4) 0.0432(10) Uani 1 1 d . . . H1 H 0.0828 0.8296 0.0313 0.052 Uiso 1 1 calc R . . C2 C 0.0280(6) 0.9304(5) 0.1934(5) 0.0458(12) Uani 1 1 d . . . H2 H -0.0060 0.9919 0.1539 0.055 Uiso 1 1 calc R . . N3 N 0.0197(5) 0.9482(4) 0.3209(4) 0.0405(9) Uani 1 1 d . . . C4 C 0.0736(5) 0.8528(4) 0.3669(5) 0.0354(10) Uani 1 1 d . . . C5 C 0.1300(5) 0.7484(4) 0.2940(4) 0.0343(10) Uani 1 1 d . . . C6 C 0.1329(5) 0.7322(4) 0.1562(5) 0.0373(11) Uani 1 1 d . . . N6 N 0.1769(5) 0.6369(4) 0.0718(4) 0.0483(11) Uani 1 1 d . . . H6 H 0.1735 0.6360 -0.0109 0.058 Uiso 1 1 calc R . . H7 H 0.2094 0.5748 0.0989 0.058 Uiso 1 1 calc R . . N7 N 0.1747(4) 0.6797(4) 0.3801(4) 0.0381(9) Uani 1 1 d . . . H3 H 0.2141 0.6094 0.3597 0.046 Uiso 1 1 calc R . . C8 C 0.1469(6) 0.7403(5) 0.5008(5) 0.0428(12) Uani 1 1 d . . . H4 H 0.1673 0.7134 0.5776 0.051 Uiso 1 1 calc R . . N9 N 0.0849(5) 0.8460(4) 0.4954(4) 0.0390(9) Uani 1 1 d . . . H5 H 0.0571 0.9000 0.5613 0.047 Uiso 1 1 calc R . . O1 O 0.2607(5) 0.4643(4) 0.2429(4) 0.0552(10) Uani 1 1 d D . . H8 H 0.168(4) 0.396(4) 0.229(6) 0.084(15) Uiso 1 1 d D . . H9 H 0.351(4) 0.433(5) 0.270(6) 0.084(15) Uiso 1 1 d D . . 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 0.0616(2) 0.0429(2) 0.0654(3) 0.01951(18) 0.00360(18) 0.01374(17) I2 0.0454(2) 0.0512(2) 0.0497(2) 0.02017(18) -0.00098(15) 0.00436(16) I3 0.0535(2) 0.0543(2) 0.0511(2) 0.01031(17) 0.00383(16) 0.01035(17) I4 0.0682(3) 0.0595(2) 0.0510(2) 0.00625(18) 0.00888(18) 0.02197(19) I5 0.0544(2) 0.0554(2) 0.0517(2) 0.00591(18) 0.00290(17) 0.00850(17) Cl1 0.0720(9) 0.0627(9) 0.0342(7) 0.0083(6) 0.0066(6) 0.0184(7) N1 0.057(2) 0.044(2) 0.029(2) 0.0098(19) 0.0026(19) 0.010(2) C2 0.057(3) 0.036(3) 0.047(3) 0.013(2) 0.001(2) 0.014(2) N3 0.055(2) 0.035(2) 0.030(2) 0.0026(18) -0.0020(18) 0.0115(18) C4 0.035(2) 0.034(3) 0.037(3) 0.006(2) 0.002(2) 0.008(2) C5 0.040(2) 0.031(2) 0.031(2) 0.005(2) 0.004(2) 0.0066(19) C6 0.035(2) 0.033(3) 0.040(3) 0.004(2) 0.004(2) 0.0033(19) N6 0.063(3) 0.050(3) 0.033(2) 0.003(2) 0.010(2) 0.023(2) N7 0.043(2) 0.034(2) 0.037(2) 0.0070(18) 0.0005(18) 0.0109(17) C8 0.044(3) 0.047(3) 0.040(3) 0.013(2) 0.001(2) 0.014(2) N9 0.049(2) 0.038(2) 0.030(2) 0.0035(18) 0.0002(18) 0.0140(18) O1 0.068(3) 0.046(2) 0.054(2) 0.0055(19) 0.009(2) 0.0226(19) __geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 I2 2.9880(5) . ? I2 I3 2.8717(5) . ? I4 I5 2.7556(6) . ? N1 C2 1.345(6) . ? N1 C6 1.364(6) . ? N1 H1 0.8600 . ? C2 N3 1.305(6) . ? C2 H2 0.9300 . ? N3 C4 1.360(6) . ? C4 N9 1.358(6) . ? C4 C5 1.369(6) . ? C5 N7 1.365(6) . ? C5 C6 1.408(6) . ? C6 N6 1.304(6) . ? N6 H6 0.8600 . ? N6 H7 0.8600 . ? N7 C8 1.328(6) . ? N7 H3 0.8600 . ? C8 N9 1.337(5) . ? C8 H4 0.9300 . ? N9 H5 0.8600 . ? O1 H8 0.933(19) . ? O1 H9 0.936(19) . ? I3 I4 3.4232(5) . ? I5 I1 3.3776(5) 1_554 ? I2 I4 4.2132(5) . ? I2 I5 4.1655(5) 1_556 ? I3 I4 4.0975(5) 2_655 ? I3 I5 4.1778(5) 2_655 ? I4 I4 4.2192(7) 2_655 ? I2 I1 4.2417(5) 2_666 ? Cl1 I1 3.9954(14) . ? 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_3 _geom_angle_publ_flag I3 I2 I1 176.973(16) . . ? C2 N1 C6 124.4(4) . . ? C2 N1 H1 117.8 . . ? C6 N1 H1 117.8 . . ? N3 C2 N1 125.7(5) . . ? N3 C2 H2 117.2 . . ? N1 C2 H2 117.2 . . ? C2 N3 C4 111.6(4) . . ? N9 C4 N3 125.7(4) . . ? N9 C4 C5 107.5(4) . . ? N3 C4 C5 126.8(4) . . ? N7 C5 C4 107.1(4) . . ? N7 C5 C6 133.6(4) . . ? C4 C5 C6 119.3(4) . . ? N6 C6 N1 120.4(4) . . ? N6 C6 C5 127.4(4) . . ? N1 C6 C5 112.2(4) . . ? C6 N6 H6 120.0 . . ? C6 N6 H7 120.0 . . ? H6 N6 H7 120.0 . . ? C8 N7 C5 108.0(4) . . ? C8 N7 H3 126.0 . . ? C5 N7 H3 126.0 . . ? N7 C8 N9 109.6(4) . . ? N7 C8 H4 125.2 . . ? N9 C8 H4 125.2 . . ? C8 N9 C4 107.8(4) . . ? C8 N9 H5 126.1 . . ? C4 N9 H5 126.1 . . ? H8 O1 H9 107(3) . . ? I5 I1 I2 81.50(1) 1_556 . ? I2 I3 I4 83.53(1) . . ? I3 I4 I5 175.37(2) . . ? I4 I5 I1 176.33(2) . 1_554 ? Cl1 I1 I2 169.03(3) . . ? I1 I2 I1 83.35(1) . 2_666 ? I3 I2 I1 93.75(1) . 2_666 ? I1 I2 I4 125.18(1) . . ? I3 I2 I4 53.84(1) . . ? I2 I4 I5 132.76(1) . . ? I1 I2 I5 53.32(1) . 1_556 ? I3 I2 I5 127.45(1) . 1_556 ? I2 I3 I4 150.78(2) . 2_655 ? I2 I3 I5 169.31(2) . 2_655 ? I5 I4 I4 120.71(2) . 2_655 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N9 H5 N3 0.86 2.02 2.858(5) 164.8 2_576 N7 H3 O1 0.86 1.85 2.655(5) 154.0 . N1 H1 Cl1 0.86 2.17 2.999(4) 161.5 1_554 N6 H6 Cl1 0.86 2.71 3.417(5) 140.0 1_554 N6 H7 O1 0.86 2.19 2.994(6) 156.1 . O1 H8 Cl1 0.933(19) 2.197(19) 3.128(4) 175(5) 2_566 O1 H9 I1 0.936(19) 3.14(3) 3.899(4) 140(4) 2_666 O1 H9 I4 0.936(19) 3.23(5) 3.706(3) 114(4) . O1 H9 I2 0.936(19) 3.29(4) 3.959(4) 130(4) . C8 H4 Cl1 0.93 2.67 3.384(5) 133.8 . C2 H2 Cl1 0.93 2.71 3.532(5) 147.5 2_576 C8 H4 I1 0.93 3.09 3.811(5) 135.2 . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.907 _refine_diff_density_min -1.039 _refine_diff_density_rms 0.150 #===End data_2 _database_code_CSD 186873 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H9 Br I5 N5 O ' _chemical_formula_weight 869.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4401(3) _cell_length_b 10.5059(4) _cell_length_c 10.6470(3) _cell_angle_alpha 102.676(2) _cell_angle_beta 92.067(2) _cell_angle_gamma 101.7656(16) _cell_volume 898.48(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 17224 _cell_measurement_theta_min 3.53 _cell_measurement_theta_max 27.87 _exptl_crystal_description 'block' _exptl_crystal_colour 'red brown' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 10.872 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.124 _exptl_absorpt_correction_T_max 0.190 _exptl_absorpt_process_details '(Blessing, 1995, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'NONIUS KappaCCD Diffractometer' _diffrn_measurement_method 'CCD' _diffrn_detector_area_resol_mean 0.76 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 17224 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 27.87 _reflns_number_total 4245 _reflns_number_gt 3104 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _publ_section_references ; collect: "Collect" data collection software, Nonius B.V., Delft, The Netherlands, 1998. HKL Scalepack & HKL Denzo: Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R.M. Sweet, Eds., Academic Press. absorption correction: R.H. Blessing (1995) Acta Cryst. A51, 33-37. R.H. Blessing (1997) J.Appl. Cryst. 30, 421-426. maXus: S.Mackay, C.J.Gilmore, C.Edwards, M. Tremayne, N. Stuart, K.Shankland maXus: a computer program for the solution and refinement of crystal structures from diffraction data", University of Glasgow, Scotland, UK, Nonius BV, Delft, The Netherlands and MacScience Co. Ltd., Yokohama, Japan (1998). Sheldrick, G. M. (1998). SHELXTL Version 5.1. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1997). SHELX-97. PC Version. University of Goettingen, Germany. ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+0.3249P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0065(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4245 _refine_ls_number_parameters 162 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.26259(6) 0.46243(4) 0.63736(5) 0.05918(15) Uani 1 1 d . . . I2 I 0.37336(5) 0.24019(4) 0.47170(4) 0.05023(14) Uani 1 1 d . . . I3 I 0.49454(5) 0.02954(5) 0.30467(4) 0.05661(15) Uani 1 1 d . . . I4 I 0.42141(6) 0.18076(5) 0.06412(5) 0.06394(16) Uani 1 1 d . . . I5 I 0.35079(6) 0.31616(5) -0.11756(4) 0.06135(15) Uani 1 1 d . . . Br1 Br 0.05470(9) 0.74791(7) 0.81962(6) 0.0575(2) Uani 1 1 d . . . N1 N 0.0824(6) 0.8320(5) 0.1241(4) 0.0445(11) Uani 1 1 d . . . H1 H 0.0815 0.8297 0.0429 0.053 Uiso 1 1 calc R . . C2 C 0.0291(8) 0.9292(6) 0.1996(6) 0.0516(15) Uani 1 1 d . . . H2 H -0.0061 0.9900 0.1596 0.062 Uiso 1 1 calc R . . N3 N 0.0205(6) 0.9493(5) 0.3251(4) 0.0427(11) Uani 1 1 d . . . C4 C 0.0775(6) 0.8551(5) 0.3725(5) 0.0376(11) Uani 1 1 d . . . C5 C 0.1378(6) 0.7503(5) 0.3009(5) 0.0377(11) Uani 1 1 d . . . C6 C 0.1396(7) 0.7337(6) 0.1674(5) 0.0411(12) Uani 1 1 d . . . N6 N 0.1873(6) 0.6400(5) 0.0857(4) 0.0521(13) Uani 1 1 d . . . H6 H 0.1832 0.6394 0.0048 0.062 Uiso 1 1 calc R . . H7 H 0.2229 0.5789 0.1128 0.062 Uiso 1 1 calc R . . N7 N 0.1830(6) 0.6821(5) 0.3872(4) 0.0427(11) Uani 1 1 d . . . H3 H 0.2236 0.6122 0.3682 0.051 Uiso 1 1 calc R . . C8 C 0.1543(7) 0.7410(6) 0.5036(5) 0.0458(13) Uani 1 1 d . . . H4 H 0.1761 0.7143 0.5790 0.055 Uiso 1 1 calc R . . N9 N 0.0881(6) 0.8465(5) 0.4969(4) 0.0433(11) Uani 1 1 d . . . H5 H 0.0580 0.8991 0.5610 0.052 Uiso 1 1 calc R . . O1 O 0.2863(6) 0.4731(5) 0.2528(4) 0.0585(12) Uani 1 1 d D . . H8 H 0.219(7) 0.387(4) 0.225(7) 0.088(19) Uiso 1 1 d D . . H9 H 0.383(5) 0.466(7) 0.292(7) 0.088(19) Uiso 1 1 d D . . 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 0.0641(3) 0.0486(3) 0.0708(3) 0.0203(2) 0.0066(2) 0.0185(2) I2 0.0477(3) 0.0514(3) 0.0546(3) 0.02156(19) 0.00096(17) 0.00827(19) I3 0.0573(3) 0.0556(3) 0.0572(3) 0.01133(19) 0.00712(18) 0.0145(2) I4 0.0692(3) 0.0615(3) 0.0614(3) 0.0037(2) 0.0126(2) 0.0249(2) I5 0.0576(3) 0.0616(3) 0.0609(3) 0.0065(2) 0.00707(19) 0.0119(2) Br1 0.0726(5) 0.0685(5) 0.0357(3) 0.0115(3) 0.0098(3) 0.0248(4) N1 0.061(3) 0.047(3) 0.030(2) 0.0082(19) 0.0054(19) 0.022(2) C2 0.063(4) 0.047(4) 0.048(3) 0.015(3) 0.001(3) 0.018(3) N3 0.054(3) 0.039(3) 0.036(2) 0.0060(19) 0.0012(19) 0.015(2) C4 0.035(3) 0.039(3) 0.037(3) 0.004(2) 0.004(2) 0.011(2) C5 0.040(3) 0.038(3) 0.034(3) 0.007(2) 0.007(2) 0.007(2) C6 0.041(3) 0.038(3) 0.040(3) 0.003(2) 0.002(2) 0.006(2) N6 0.069(3) 0.055(3) 0.038(3) 0.008(2) 0.015(2) 0.030(3) N7 0.046(3) 0.039(3) 0.046(3) 0.008(2) 0.004(2) 0.019(2) C8 0.056(4) 0.051(4) 0.035(3) 0.014(2) 0.006(2) 0.019(3) N9 0.055(3) 0.039(3) 0.037(2) 0.0054(19) 0.0054(19) 0.019(2) O1 0.074(3) 0.046(3) 0.058(3) 0.005(2) 0.010(2) 0.028(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 I2 2.9391(6) . ? I2 I3 2.9040(6) . ? I4 I5 2.7551(8) . ? N1 C2 1.321(8) . ? N1 C6 1.382(7) . ? N1 H1 0.8600 . ? C2 N3 1.313(7) . ? C2 H2 0.9300 . ? N3 C4 1.364(7) . ? C4 N9 1.349(7) . ? C4 C5 1.392(8) . ? C5 N7 1.371(7) . ? C5 C6 1.394(7) . ? C6 N6 1.303(7) . ? N6 H6 0.8600 . ? N6 H7 0.8600 . ? N7 C8 1.313(7) . ? N7 H3 0.8600 . ? C8 N9 1.353(7) . ? C8 H4 0.9300 . ? N9 H5 0.8600 . ? O1 H8 0.94(2) . ? O1 H9 0.93(2) . ? I3 I4 3.3964(7) . ? I5 I1 3.4366(6) 1_554 ? I2 I4 4.2927(6) . ? I2 I5 4.2881(6) 1_556 ? I3 I4 4.2232(7) 2_655 ? I3 I5 4.2201(7) 2_655 ? I4 I4 4.2378(10) 2_655 ? I2 I1 4.2994(6) 2_666 ? Br1 I1 3.9594(8) . ? 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_3 _geom_angle_publ_flag I3 I2 I1 177.366(18) . . ? C2 N1 C6 124.2(5) . . ? C2 N1 H1 117.9 . . ? C6 N1 H1 117.9 . . ? N3 C2 N1 127.0(6) . . ? N3 C2 H2 116.5 . . ? N1 C2 H2 116.5 . . ? C2 N3 C4 110.9(5) . . ? N9 C4 N3 126.7(5) . . ? N9 C4 C5 107.1(5) . . ? N3 C4 C5 126.2(5) . . ? N7 C5 C4 106.4(4) . . ? N7 C5 C6 134.0(5) . . ? C4 C5 C6 119.6(5) . . ? N6 C6 N1 120.1(5) . . ? N6 C6 C5 127.8(5) . . ? N1 C6 C5 112.2(5) . . ? C6 N6 H6 120.0 . . ? C6 N6 H7 120.0 . . ? H6 N6 H7 120.0 . . ? C8 N7 C5 108.8(5) . . ? C8 N7 H3 125.6 . . ? C5 N7 H3 125.6 . . ? N7 C8 N9 109.4(5) . . ? N7 C8 H4 125.3 . . ? N9 C8 H4 125.3 . . ? C4 N9 C8 108.2(5) . . ? C4 N9 H5 125.9 . . ? C8 N9 H5 125.9 . . ? H8 O1 H9 109(3) . . ? I5 I1 I2 84.15(1) 1_556 . ? I2 I3 I4 85.52(1) . . ? I3 I4 I5 175.57(2) . . ? I4 I5 I1 175.45(2) . 1_554 ? Br1 I1 I2 171.03(2) . . ? I1 I2 I1 87.02(1) . 2_666 ? I3 I2 I1 90.35(1) . 2_666 ? I1 I2 I4 126.53(1) . . ? I3 I2 I4 52.07(1) . . ? I2 I4 I5 133.19(2) . . ? I1 I2 I5 52.87(1) . 1_556 ? I3 I2 I5 128.37(2) . 1_556 ? I2 I3 I4 151.72(2) . 2_655 ? I2 I3 I5 169.11(2) . 2_655 ? I5 I4 I4 118.22(2) . 2_655 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N9 H5 N3 0.86 2.02 2.859(6) 164.4 2_576 N7 H3 O1 0.86 1.87 2.668(6) 153.5 . N1 H1 Br1 0.86 2.33 3.154(4) 160.9 1_554 N6 H6 Br1 0.86 2.77 3.502(5) 143.3 1_554 N6 H7 O1 0.86 2.16 2.966(7) 156.4 . O1 H8 Br1 0.94(2) 2.42(4) 3.255(5) 147(6) 2_566 O1 H9 I1 0.93(2) 2.96(3) 3.822(5) 155(6) 2_666 O1 H8 I4 0.94(2) 3.26(7) 3.695(4) 111(5) . O1 H9 I2 0.93(2) 3.35(6) 3.883(5) 119(5) . C8 H4 Br1 0.93 2.77 3.486(6) 134.4 . C2 H2 Br1 0.93 2.83 3.650(6) 147.9 2_576 C8 H4 I1 0.93 3.07 3.775(6) 134.4 . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.224 _refine_diff_density_min -1.281 _refine_diff_density_rms 0.202 #===End data_3 _database_code_CSD 186874 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H9 Br I5 N5 O ' _chemical_formula_weight 934.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P 2(1)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.4041(4) _cell_length_b 12.8322(5) _cell_length_c 12.5015(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.352(2) _cell_angle_gamma 90.00 _cell_volume 1918.88(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 32992 _cell_measurement_theta_min 3.41 _cell_measurement_theta_max 27.88 _exptl_crystal_description 'block' _exptl_crystal_colour 'brown' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1640 _exptl_absorpt_coefficient_mu 9.716 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.175 _exptl_absorpt_correction_T_max 0.280 _exptl_absorpt_process_details '(Blessing, 1995, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'NONIUS KappaCCD Diffractometer' _diffrn_measurement_method 'CCD' _diffrn_detector_area_resol_mean 0.76 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 32992 _diffrn_reflns_av_R_equivalents 0.0583 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 27.88 _reflns_number_total 4564 _reflns_number_gt 3402 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _publ_section_references ; collect: "Collect" data collection software, Nonius B.V., Delft, The Netherlands, 1998. HKL Scalepack & HKL Denzo: Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R.M. Sweet, Eds., Academic Press. absorption correction: R.H. Blessing (1995) Acta Cryst. A51, 33-37. R.H. Blessing (1997) J.Appl. Cryst. 30, 421-426. maXus: S.Mackay, C.J.Gilmore, C.Edwards, M. Tremayne, N. Stuart, K.Shankland maXus: a computer program for the solution and refinement of crystal structures from diffraction data", University of Glasgow, Scotland, UK, Nonius BV, Delft, The Netherlands and MacScience Co. Ltd., Yokohama, Japan (1998). Sheldrick, G. M. (1998). SHELXTL Version 5.1. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1997). SHELX-97. PC Version. University of Goettingen, Germany. ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0256P)^2^+2.2113P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00088(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4564 _refine_ls_number_parameters 177 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0687 _refine_ls_wR_factor_gt 0.0623 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.03375(3) -0.05536(3) 0.69800(3) 0.05983(12) Uani 1 1 d . . . I2 I -0.13094(3) 0.10133(3) 0.72227(3) 0.05401(11) Uani 1 1 d . . . I3 I -0.29390(3) 0.25897(3) 0.74480(3) 0.05842(11) Uani 1 1 d . . . I4 I -0.08356(3) 0.44035(3) 0.70163(3) 0.05975(11) Uani 1 1 d . . . I5 I 0.07916(3) 0.57500(3) 0.66415(3) 0.05289(11) Uani 1 1 d . . . I6 I 0.26721(3) 0.73294(3) 0.63932(3) 0.06227(12) Uani 1 1 d . . . N1 N 0.4069(3) 0.3112(3) 0.5180(3) 0.0464(10) Uani 1 1 d . . . H1 H 0.4190 0.3771 0.5164 0.056 Uiso 1 1 calc R . . C2 C 0.4856(4) 0.2454(4) 0.5010(4) 0.0458(11) Uani 1 1 d . . . H2 H 0.5489 0.2753 0.4871 0.055 Uiso 1 1 calc R . . N3 N 0.4812(3) 0.1446(3) 0.5024(3) 0.0422(9) Uani 1 1 d . . . C4 C 0.3859(4) 0.1103(3) 0.5237(3) 0.0378(10) Uani 1 1 d . . . C5 C 0.3008(4) 0.1699(3) 0.5408(3) 0.0384(10) Uani 1 1 d . . . C6 C 0.3089(4) 0.2788(4) 0.5377(4) 0.0443(11) Uani 1 1 d . . . N6 N 0.2334(4) 0.3467(3) 0.5506(4) 0.0586(11) Uani 1 1 d . . . H6 H 0.2455 0.4124 0.5466 0.070 Uiso 1 1 calc R . . H7 H 0.1722 0.3253 0.5629 0.070 Uiso 1 1 calc R . . N7 N 0.2191(3) 0.1036(3) 0.5566(3) 0.0441(9) Uani 1 1 d . . . H3 H 0.1564 0.1216 0.5683 0.053 Uiso 1 1 calc R . . C8 C 0.2547(4) 0.0076(4) 0.5506(4) 0.0472(11) Uani 1 1 d . . . H4 H 0.2160 -0.0524 0.5595 0.057 Uiso 1 1 calc R . . N9 N 0.3546(3) 0.0096(3) 0.5300(3) 0.0414(9) Uani 1 1 d . . . H5 H 0.3931 -0.0442 0.5220 0.050 Uiso 1 1 calc R . . O1 O 0.0426(3) 0.2295(3) 0.5674(3) 0.0676(11) Uani 1 1 d D . . O2 O 0.3683(4) 0.5296(3) 0.4987(3) 0.0727(11) Uani 1 1 d D . . H8 H -0.021(4) 0.228(6) 0.504(3) 0.126(15) Uiso 1 1 d D . . H9 H 0.013(5) 0.243(6) 0.629(3) 0.126(15) Uiso 1 1 d D . . H10 H 0.322(5) 0.541(6) 0.426(2) 0.126(15) Uiso 1 1 d D . . H11 H 0.340(6) 0.572(5) 0.547(4) 0.126(15) Uiso 1 1 d D . . 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 0.0573(2) 0.0646(2) 0.0608(2) 0.00208(17) 0.02117(17) -0.00080(17) I2 0.0541(2) 0.0628(2) 0.04474(19) -0.00011(15) 0.01246(15) -0.01546(16) I3 0.0543(2) 0.0630(2) 0.0538(2) 0.00210(16) 0.00693(16) 0.00090(17) I4 0.0537(2) 0.0640(2) 0.0606(2) 0.00251(17) 0.01339(16) -0.00155(17) I5 0.0568(2) 0.0572(2) 0.04447(18) 0.00321(14) 0.01292(14) 0.00617(16) I6 0.0655(2) 0.0488(2) 0.0818(3) 0.00724(17) 0.0358(2) 0.00019(17) N1 0.057(3) 0.033(2) 0.053(2) -0.0036(17) 0.0198(19) -0.0088(18) C2 0.046(3) 0.048(3) 0.047(3) -0.004(2) 0.017(2) -0.009(2) N3 0.043(2) 0.040(2) 0.044(2) -0.0030(17) 0.0128(17) -0.0038(18) C4 0.038(2) 0.038(3) 0.036(2) -0.0007(18) 0.0077(18) -0.001(2) C5 0.041(3) 0.037(2) 0.037(2) -0.0007(18) 0.0095(19) -0.0021(19) C6 0.053(3) 0.040(3) 0.041(2) -0.004(2) 0.014(2) 0.001(2) N6 0.061(3) 0.038(2) 0.083(3) -0.001(2) 0.032(2) 0.006(2) N7 0.038(2) 0.042(2) 0.053(2) -0.0018(17) 0.0140(17) -0.0029(18) C8 0.047(3) 0.042(3) 0.054(3) 0.000(2) 0.015(2) -0.006(2) N9 0.043(2) 0.034(2) 0.048(2) -0.0018(16) 0.0128(17) 0.0044(17) O1 0.062(2) 0.069(3) 0.079(3) 0.014(2) 0.032(2) 0.012(2) O2 0.094(3) 0.045(2) 0.070(3) -0.0014(19) 0.007(2) 0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 I2 2.9388(5) . ? I2 I3 2.9255(5) . ? I4 I5 2.7892(5) . ? N1 C2 1.349(6) . ? N1 C6 1.367(6) . ? N1 H1 0.8600 . ? C2 N3 1.295(6) . ? C2 H2 0.9300 . ? N3 C4 1.352(6) . ? C4 N9 1.357(6) . ? C4 C5 1.365(6) . ? C5 N7 1.376(6) . ? C5 C6 1.402(6) . ? C6 N6 1.319(6) . ? N6 H6 0.8600 . ? N6 H7 0.8600 . ? N7 C8 1.318(6) . ? N7 H3 0.8600 . ? C8 N9 1.331(6) . ? C8 H4 0.9300 . ? N9 H5 0.8600 . ? O1 H8 0.95(2) . ? O1 H9 0.956(19) . ? O2 H10 0.946(19) . ? O2 H11 0.943(19) . ? I3 I4 3.6416(5) . ? I5 I6 3.1668(5) . ? I1 I6 4.1748(5) 1_545 ? I1 I3 4.0206(5) 2_446 ? 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_3 _geom_angle_publ_flag I3 I2 I1 179.338(16) . . ? C2 N1 C6 123.6(4) . . ? C2 N1 H1 118.2 . . ? C6 N1 H1 118.2 . . ? N3 C2 N1 126.0(4) . . ? N3 C2 H2 117.0 . . ? N1 C2 H2 117.0 . . ? C2 N3 C4 111.7(4) . . ? N3 C4 N9 126.8(4) . . ? N3 C4 C5 126.9(4) . . ? N9 C4 C5 106.2(4) . . ? C4 C5 N7 107.8(4) . . ? C4 C5 C6 119.3(4) . . ? N7 C5 C6 132.9(4) . . ? N6 C6 N1 121.0(4) . . ? N6 C6 C5 126.6(5) . . ? N1 C6 C5 112.4(4) . . ? C6 N6 H6 120.0 . . ? C6 N6 H7 120.0 . . ? H6 N6 H7 120.0 . . ? C8 N7 C5 107.4(4) . . ? C8 N7 H3 126.3 . . ? C5 N7 H3 126.3 . . ? N7 C8 N9 109.6(4) . . ? N7 C8 H4 125.2 . . ? N9 C8 H4 125.2 . . ? C8 N9 C4 108.9(4) . . ? C8 N9 H5 125.5 . . ? C4 N9 H5 125.5 . . ? H8 O1 H9 105(3) . . ? H10 O2 H11 107(3) . . ? I2 I3 I4 83.53(1) . . ? I3 I4 I5 178.28(2) . . ? I4 I5 I6 175.95(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N9 H5 N3 0.86 2.11 2.944(5) 164.3 3_656 N6 H7 O1 0.86 2.04 2.859(6) 160.0 . N7 H3 O1 0.86 1.98 2.754(5) 149.8 . N1 H1 O2 0.86 2.05 2.843(6) 153.0 . N6 H6 O2 0.86 2.33 3.050(6) 141.6 . O1 H8 I6 0.95(2) 3.15(3) 4.052(4) 159(5) 3_566 O1 H8 I5 0.95(2) 3.25(7) 3.826(4) 121(5) 3_566 O1 H9 I2 0.956(19) 2.99(6) 3.645(4) 127(5) . O1 H9 I4 0.956(19) 3.04(6) 3.738(4) 131(5) . O2 H10 I4 0.946(19) 2.98(5) 3.770(4) 142(5) 3_566 O2 H10 I3 0.946(19) 3.30(6) 3.999(4) 133(6) 3_566 O2 H10 I2 0.946(19) 3.32(5) 3.846(4) 118(4) 4_665 O2 H11 I6 0.943(19) 2.64(3) 3.554(4) 163(6) . C8 H4 I1 0.93 3.19 3.773(5) 122.5 . C8 H4 I6 0.93 2.94 3.686(5) 138.1 1_545 C2 H2 I6 0.93 3.10 3.925(5) 148.5 3_666 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.673 _refine_diff_density_min -0.829 _refine_diff_density_rms 0.122 #===End