# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Derek Woollins' 'Petr Kilian' 'Alexandra M.Z.Slawin' 'David M.A.Taddei' _publ_contact_author_name 'Prof Derek Woollins' _publ_contact_author_address ; St Andrews UNITED KINGDOM ; _publ_contact_author_email JDW3@ST-AND.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Synthesis and full characterisation of 6-chloro-2-iodopurine, a template for the functionalisation of purines ; data_10 _database_code_depnum_ccdc_archive 'CCDC 221982' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 Cl I N4 O' _chemical_formula_sum 'C10 H10 Cl I N4 O' _chemical_formula_weight 364.57 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.8021(10) _cell_length_b 11.860(2) _cell_length_c 21.790(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.098(4) _cell_angle_gamma 90.00 _cell_volume 1236.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 74 _cell_measurement_theta_min 12 _cell_measurement_theta_max 168 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .1 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.959 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 2.796 _exptl_absorpt_correction_type MULTISCAN _exptl_absorpt_correction_T_min 0.694487 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5159 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 23.27 _reflns_number_total 1726 _reflns_number_gt 1536 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0339P)^2^+1.7376P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0010(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1726 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0329 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0645 _refine_ls_wR_factor_gt 0.0624 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 N1 N 0.7438(7) 0.2419(3) 0.40047(16) 0.0194(8) Uani 1 1 d . . . C2 C 0.6795(8) 0.2744(4) 0.34275(19) 0.0193(9) Uani 1 1 d . . . I2 I 0.37872(5) 0.17419(2) 0.291844(13) 0.02546(15) Uani 1 1 d . . . N3 N 0.7836(7) 0.3584(3) 0.31100(17) 0.0219(8) Uani 1 1 d . . . C4 C 0.9819(8) 0.4196(3) 0.3408(2) 0.0202(9) Uani 1 1 d . . . Cl4 Cl 1.1405(2) 0.52270(9) 0.29977(5) 0.0263(3) Uani 1 1 d . . . C5 C 1.0732(8) 0.4000(3) 0.4016(2) 0.0197(9) Uani 1 1 d . . . C6 C 0.9434(8) 0.3086(3) 0.4283(2) 0.0202(10) Uani 1 1 d . . . N7 N 1.0647(7) 0.3009(3) 0.48751(16) 0.0213(8) Uani 1 1 d . . . C8 C 1.2596(9) 0.3861(4) 0.4931(2) 0.0238(10) Uani 1 1 d . . . H8A H 1.3757 0.3993 0.5300 0.029 Uiso 1 1 calc R . . N9 N 1.2724(7) 0.4471(3) 0.44391(17) 0.0226(8) Uani 1 1 d . . . C10 C 1.0067(9) 0.2157(4) 0.5326(2) 0.0236(10) Uani 1 1 d . . . H10A H 0.8327 0.1743 0.5174 0.028 Uiso 1 1 calc R . . O11 O 1.2375(6) 0.1388(2) 0.53540(14) 0.0261(7) Uani 1 1 d . . . C12 C 1.1851(11) 0.0441(4) 0.5751(2) 0.0338(12) Uani 1 1 d . . . H12A H 1.3462 -0.0083 0.5767 0.041 Uiso 1 1 calc R . . H12B H 1.0177 0.0027 0.5575 0.041 Uiso 1 1 calc R . . C13 C 1.1405(10) 0.0810(4) 0.6392(2) 0.0320(11) Uani 1 1 d . . . H13A H 1.3170 0.1125 0.6591 0.038 Uiso 1 1 calc R . . H13B H 1.0890 0.0150 0.6635 0.038 Uiso 1 1 calc R . . C14 C 0.9147(10) 0.1682(4) 0.6391(2) 0.0362(12) Uani 1 1 d . . . H14A H 0.9076 0.1984 0.6813 0.043 Uiso 1 1 calc R . . H14B H 0.7318 0.1330 0.6263 0.043 Uiso 1 1 calc R . . C15 C 0.9681(9) 0.2645(4) 0.5952(2) 0.0275(10) Uani 1 1 d . . . H15A H 0.8078 0.3173 0.5922 0.033 Uiso 1 1 calc R . . H15B H 1.1378 0.3067 0.6108 0.033 Uiso 1 1 calc 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 N1 0.0204(18) 0.0164(19) 0.021(2) -0.0015(15) -0.0007(15) 0.0010(15) C2 0.015(2) 0.023(2) 0.019(2) -0.0059(19) -0.0008(18) 0.0022(18) I2 0.01943(19) 0.0276(2) 0.0283(2) -0.00913(13) -0.00345(12) 0.00127(11) N3 0.0180(17) 0.0200(19) 0.027(2) -0.0021(16) 0.0001(16) 0.0026(15) C4 0.023(2) 0.018(2) 0.020(2) 0.0032(18) 0.0030(19) 0.0058(18) Cl4 0.0317(6) 0.0246(6) 0.0228(6) 0.0058(4) 0.0031(5) -0.0012(5) C5 0.017(2) 0.015(2) 0.026(2) -0.0025(18) -0.0010(18) 0.0011(17) C6 0.021(2) 0.018(2) 0.022(2) -0.0033(19) 0.0029(19) 0.0044(18) N7 0.0261(19) 0.018(2) 0.019(2) 0.0008(15) -0.0011(16) -0.0026(15) C8 0.027(2) 0.019(2) 0.024(2) -0.0024(19) -0.0046(19) -0.0048(19) N9 0.0218(19) 0.022(2) 0.023(2) 0.0042(16) -0.0033(16) -0.0026(15) C10 0.021(2) 0.026(2) 0.023(2) 0.000(2) -0.0017(19) -0.0001(19) O11 0.0317(17) 0.0205(16) 0.0265(17) 0.0027(13) 0.0059(14) 0.0020(13) C12 0.043(3) 0.021(3) 0.036(3) 0.007(2) 0.000(2) 0.000(2) C13 0.035(3) 0.041(3) 0.020(2) 0.012(2) -0.003(2) -0.007(2) C14 0.030(3) 0.056(3) 0.023(3) -0.002(2) 0.006(2) -0.010(2) C15 0.024(2) 0.035(3) 0.024(2) -0.002(2) 0.0040(19) 0.004(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 N1 C2 1.325(5) . ? N1 C6 1.345(5) . ? C2 N3 1.336(6) . ? C2 I2 2.108(4) . ? N3 C4 1.321(6) . ? C4 C5 1.378(6) . ? C4 Cl4 1.730(4) . ? C5 N9 1.385(5) . ? C5 C6 1.403(6) . ? C6 N7 1.370(6) . ? N7 C8 1.375(5) . ? N7 C10 1.454(6) . ? C8 N9 1.299(6) . ? C10 O11 1.432(5) . ? C10 C15 1.507(6) . ? O11 C12 1.453(5) . ? C12 C13 1.496(7) . ? C13 C14 1.498(7) . ? C14 C15 1.526(6) . ? 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 C2 N1 C6 110.7(4) . . ? N1 C2 N3 130.0(4) . . ? N1 C2 I2 115.2(3) . . ? N3 C2 I2 114.7(3) . . ? C4 N3 C2 116.2(4) . . ? N3 C4 C5 122.3(4) . . ? N3 C4 Cl4 117.7(3) . . ? C5 C4 Cl4 119.9(3) . . ? C4 C5 N9 135.5(4) . . ? C4 C5 C6 114.5(4) . . ? N9 C5 C6 110.0(4) . . ? N1 C6 N7 127.7(4) . . ? N1 C6 C5 126.3(4) . . ? N7 C6 C5 105.9(3) . . ? C6 N7 C8 105.3(4) . . ? C6 N7 C10 126.3(4) . . ? C8 N7 C10 128.4(4) . . ? N9 C8 N7 114.7(4) . . ? C8 N9 C5 104.1(3) . . ? O11 C10 N7 106.1(3) . . ? O11 C10 C15 111.3(4) . . ? N7 C10 C15 113.0(4) . . ? C10 O11 C12 110.1(3) . . ? O11 C12 C13 112.1(4) . . ? C12 C13 C14 111.4(4) . . ? C13 C14 C15 110.8(4) . . ? C10 C15 C14 108.7(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 N3 0.8(6) . . . . ? C6 N1 C2 I2 178.0(3) . . . . ? N1 C2 N3 C4 0.1(6) . . . . ? I2 C2 N3 C4 -177.0(3) . . . . ? C2 N3 C4 C5 -1.4(6) . . . . ? C2 N3 C4 Cl4 175.3(3) . . . . ? N3 C4 C5 N9 179.2(4) . . . . ? Cl4 C4 C5 N9 2.5(7) . . . . ? N3 C4 C5 C6 1.5(6) . . . . ? Cl4 C4 C5 C6 -175.2(3) . . . . ? C2 N1 C6 N7 -179.4(4) . . . . ? C2 N1 C6 C5 -0.6(6) . . . . ? C4 C5 C6 N1 -0.4(6) . . . . ? N9 C5 C6 N1 -178.7(4) . . . . ? C4 C5 C6 N7 178.6(4) . . . . ? N9 C5 C6 N7 0.3(5) . . . . ? N1 C6 N7 C8 178.5(4) . . . . ? C5 C6 N7 C8 -0.5(4) . . . . ? N1 C6 N7 C10 1.8(7) . . . . ? C5 C6 N7 C10 -177.2(4) . . . . ? C6 N7 C8 N9 0.5(5) . . . . ? C10 N7 C8 N9 177.2(4) . . . . ? N7 C8 N9 C5 -0.3(5) . . . . ? C4 C5 N9 C8 -177.8(5) . . . . ? C6 C5 N9 C8 0.0(5) . . . . ? C6 N7 C10 O11 103.5(4) . . . . ? C8 N7 C10 O11 -72.5(5) . . . . ? C6 N7 C10 C15 -134.3(4) . . . . ? C8 N7 C10 C15 49.7(6) . . . . ? N7 C10 O11 C12 -174.5(3) . . . . ? C15 C10 O11 C12 62.2(5) . . . . ? C10 O11 C12 C13 -58.9(5) . . . . ? O11 C12 C13 C14 54.0(5) . . . . ? C12 C13 C14 C15 -51.6(5) . . . . ? O11 C10 C15 C14 -59.6(5) . . . . ? N7 C10 C15 C14 -178.8(3) . . . . ? C13 C14 C15 C10 53.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.767 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.096 data_11 _database_code_depnum_ccdc_archive 'CCDC 221983' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H2 Cl I N4.H2 O' _chemical_formula_sum 'C5 H4 Cl I N4 O' _chemical_formula_weight 298.47 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.172(2) _cell_length_b 16.732(5) _cell_length_c 7.577(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.863(4) _cell_angle_gamma 90.00 _cell_volume 818.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 86 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 4.194 _exptl_absorpt_correction_type MULTISCAN _exptl_absorpt_correction_T_min 0.738347 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4704 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.38 _reflns_number_total 1448 _reflns_number_gt 1324 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0446P)^2^+2.6120P] 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 0.0009(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1448 _refine_ls_number_parameters 122 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0347 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0753 _refine_ls_wR_factor_gt 0.0727 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.003 _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 N1 N 0.2209(6) -0.1157(2) 0.0239(6) 0.0146(8) Uani 1 1 d . . . I2 I 0.22391(5) -0.220960(16) 0.33602(4) 0.01561(15) Uani 1 1 d . . . C2 C 0.2359(7) -0.1111(3) 0.2073(7) 0.0151(9) Uani 1 1 d . . . N3 N 0.2640(6) -0.0462(2) 0.3185(6) 0.0148(8) Uani 1 1 d . . . C4 C 0.2753(6) 0.0206(3) 0.2248(7) 0.0135(9) Uani 1 1 d . . . C5 C 0.2636(7) 0.0245(3) 0.0362(7) 0.0135(9) Uani 1 1 d . . . Cl6 Cl 0.21099(18) -0.05165(7) -0.29720(16) 0.0166(3) Uani 1 1 d . . . C6 C 0.2342(7) -0.0471(3) -0.0619(7) 0.0133(9) Uani 1 1 d . . . N7 N 0.2841(6) 0.1036(2) -0.0110(6) 0.0168(8) Uani 1 1 d . . . C8 C 0.3046(7) 0.1433(3) 0.1452(7) 0.0178(10) Uani 1 1 d . . . H8A H 0.3212 0.1997 0.1557 0.021 Uiso 1 1 calc R . . N9 N 0.3002(6) 0.0969(2) 0.2924(6) 0.0166(8) Uani 1 1 d D . . H9A H 0.323(9) 0.115(3) 0.424(3) 0.025(15) Uiso 1 1 d D . . O10 O 0.2491(5) 0.1587(2) 0.6147(5) 0.0203(7) Uani 1 1 d D . . H10A H 0.271(9) 0.136(3) 0.742(4) 0.030(16) Uiso 1 1 d D . . H10B H 0.0984(18) 0.164(5) 0.543(12) 0.08(3) 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 N1 0.0137(19) 0.0142(18) 0.016(2) 0.0005(15) 0.0070(16) 0.0016(15) I2 0.0218(2) 0.0132(2) 0.0141(2) 0.00158(11) 0.01002(15) 0.00036(10) C2 0.012(2) 0.015(2) 0.018(2) 0.0012(18) 0.0064(19) -0.0011(17) N3 0.0165(19) 0.0170(19) 0.0122(19) 0.0009(16) 0.0076(16) 0.0023(15) C4 0.007(2) 0.016(2) 0.014(2) -0.0010(17) 0.0005(18) -0.0022(16) C5 0.011(2) 0.016(2) 0.014(2) 0.0013(17) 0.0060(18) 0.0027(16) Cl6 0.0221(6) 0.0168(5) 0.0124(5) 0.0001(4) 0.0090(5) -0.0006(4) C6 0.010(2) 0.020(2) 0.009(2) -0.0003(18) 0.0029(17) 0.0023(17) N7 0.018(2) 0.0133(18) 0.019(2) -0.0001(16) 0.0075(17) 0.0002(15) C8 0.021(2) 0.011(2) 0.019(2) -0.0023(18) 0.007(2) -0.0002(17) N9 0.022(2) 0.0159(19) 0.014(2) -0.0015(16) 0.0098(17) 0.0001(15) O10 0.026(2) 0.0203(18) 0.0163(17) -0.0002(14) 0.0106(16) -0.0023(14) _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 N1 C6 1.344(6) . ? N1 C2 1.348(6) . ? I2 C2 2.100(5) . ? C2 N3 1.336(6) . ? N3 C4 1.344(6) . ? C4 N9 1.359(6) . ? C4 C5 1.396(7) . ? C5 C6 1.377(6) . ? C5 N7 1.394(6) . ? Cl6 C6 1.718(5) . ? N7 C8 1.308(7) . ? C8 N9 1.370(7) . ? C8 H8A 0.9500 . ? N9 H9A 0.9800(11) . ? O10 H10A 0.9800(11) . ? O10 H10B 0.9800(11) . ? 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 C6 N1 C2 117.3(4) . . ? N3 C2 N1 128.2(4) . . ? N3 C2 I2 116.4(3) . . ? N1 C2 I2 115.3(3) . . ? C2 N3 C4 111.7(4) . . ? N3 C4 N9 127.6(4) . . ? N3 C4 C5 126.1(4) . . ? N9 C4 C5 106.3(4) . . ? C6 C5 N7 134.0(4) . . ? C6 C5 C4 116.0(4) . . ? N7 C5 C4 110.0(4) . . ? N1 C6 C5 120.6(4) . . ? N1 C6 Cl6 117.9(3) . . ? C5 C6 Cl6 121.5(4) . . ? C8 N7 C5 103.4(4) . . ? N7 C8 N9 114.6(4) . . ? N7 C8 H8A 122.7 . . ? N9 C8 H8A 122.7 . . ? C4 N9 C8 105.7(4) . . ? C4 N9 H9A 127(3) . . ? C8 N9 H9A 127(3) . . ? H10A O10 H10B 105(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 N3 -0.4(7) . . . . ? C6 N1 C2 I2 -178.0(3) . . . . ? N1 C2 N3 C4 0.6(6) . . . . ? I2 C2 N3 C4 178.2(3) . . . . ? C2 N3 C4 N9 179.0(4) . . . . ? C2 N3 C4 C5 -1.0(6) . . . . ? N3 C4 C5 C6 1.2(7) . . . . ? N9 C4 C5 C6 -178.9(4) . . . . ? N3 C4 C5 N7 -179.2(4) . . . . ? N9 C4 C5 N7 0.8(5) . . . . ? C2 N1 C6 C5 0.5(6) . . . . ? C2 N1 C6 Cl6 -178.9(3) . . . . ? N7 C5 C6 N1 179.7(4) . . . . ? C4 C5 C6 N1 -0.8(6) . . . . ? N7 C5 C6 Cl6 -1.0(7) . . . . ? C4 C5 C6 Cl6 178.5(3) . . . . ? C6 C5 N7 C8 178.9(5) . . . . ? C4 C5 N7 C8 -0.6(5) . . . . ? C5 N7 C8 N9 0.2(5) . . . . ? N3 C4 N9 C8 179.4(4) . . . . ? C5 C4 N9 C8 -0.6(5) . . . . ? N7 C8 N9 C4 0.2(6) . . . . ? 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 H9A O10 0.9800(11) 1.90(2) 2.819(5) 156(5) . O10 H10A N7 0.9800(11) 1.914(11) 2.887(5) 171(5) 1_556 O10 H10B Cl6 0.9800(11) 2.89(7) 3.600(4) 130(6) 3 O10 H10B I2 0.9800(11) 2.99(7) 3.720(4) 132(7) 3_556 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.38 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 1.141 _refine_diff_density_min -1.020 _refine_diff_density_rms 0.158