# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_111031_wmy_4_61 _database_code_depnum_ccdc_archive 'CCDC 877900' #TrackingRef '- 4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H19 I N4 O4' _chemical_formula_sum 'C15 H19 I N4 O4' _chemical_formula_weight 446.24 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' I I -0.4742 1.8119 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 12.5720(7) _cell_length_b 9.3235(5) _cell_length_c 15.1484(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.258(4) _cell_angle_gamma 90.00 _cell_volume 1775.61(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2620 _cell_measurement_theta_min 3.0250 _cell_measurement_theta_max 29.2177 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 1.830 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5355 _exptl_absorpt_correction_T_max 0.6783 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _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 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9033 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3241 _reflns_number_gt 2579 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0401P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3241 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0829 _refine_ls_wR_factor_gt 0.0752 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.03079(2) 0.36610(3) 1.117278(15) 0.05430(13) Uani 1 1 d . . . O1 O 0.6085(2) -0.0010(4) 0.8320(2) 0.0795(9) Uani 1 1 d . . . O2 O 0.6122(3) 0.1645(4) 0.9303(3) 0.0885(11) Uani 1 1 d . . . O3 O 0.2851(2) -0.2001(3) 0.73851(19) 0.0694(8) Uani 1 1 d . . . O4 O 0.1342(2) -0.1093(3) 0.77404(17) 0.0598(7) Uani 1 1 d . . . N1 N 0.5652(3) 0.0797(4) 0.8842(2) 0.0572(8) Uani 1 1 d . . . N2 N 0.2318(3) -0.1154(3) 0.78144(19) 0.0468(8) Uani 1 1 d . . . N3 N 0.1223(2) 0.0729(3) 0.90494(16) 0.0394(6) Uani 1 1 d . . . H3 H 0.0847 0.0199 0.8704 0.047 Uiso 1 1 calc R . . N4 N 0.0742(2) 0.1636(3) 0.96401(17) 0.0388(7) Uani 1 1 d . . . C1 C 0.4497(3) 0.0730(4) 0.8917(2) 0.0433(8) Uani 1 1 d . . . C2 C 0.3943(3) -0.0168(3) 0.8369(2) 0.0419(8) Uani 1 1 d . . . H2 H 0.4298 -0.0746 0.7966 0.050 Uiso 1 1 calc R . . C3 C 0.2856(3) -0.0202(3) 0.84248(19) 0.0375(7) Uani 1 1 d . . . C4 C 0.2287(3) 0.0683(3) 0.90196(19) 0.0363(7) Uani 1 1 d . . . C5 C 0.2906(3) 0.1545(3) 0.9588(2) 0.0422(8) Uani 1 1 d . . . H5 H 0.2569 0.2104 1.0011 0.051 Uiso 1 1 calc R . . C6 C 0.3977(3) 0.1577(4) 0.9532(2) 0.0476(9) Uani 1 1 d . . . H6 H 0.4368 0.2169 0.9906 0.057 Uiso 1 1 calc R . . C7 C -0.0268(3) 0.1803(3) 0.9582(2) 0.0366(7) Uani 1 1 d . . . C8 C -0.0741(3) 0.2800(3) 1.0223(2) 0.0392(8) Uani 1 1 d . . . C9 C -0.1738(3) 0.3236(4) 1.0214(2) 0.0472(9) Uani 1 1 d . . . H9 H -0.2173 0.2820 0.9787 0.057 Uiso 1 1 calc R . . C10 C -0.2259(3) 0.4309(4) 1.0799(3) 0.0590(10) Uani 1 1 d . . . H10A H -0.1985 0.5253 1.0658 0.071 Uiso 1 1 calc R . . H10B H -0.2064 0.4101 1.1406 0.071 Uiso 1 1 calc R . . C11 C -0.3457(4) 0.4343(6) 1.0726(3) 0.0799(14) Uani 1 1 d . . . H11A H -0.3660 0.4529 1.0126 0.120 Uiso 1 1 calc R . . H11C H -0.3732 0.5087 1.1100 0.120 Uiso 1 1 calc R . . H11B H -0.3742 0.3434 1.0908 0.120 Uiso 1 1 calc R . . C12 C -0.0957(3) 0.1114(4) 0.8882(2) 0.0419(8) Uani 1 1 d . . . H12B H -0.1688 0.1091 0.9083 0.050 Uiso 1 1 calc R . . H12A H -0.0727 0.0132 0.8792 0.050 Uiso 1 1 calc R . . C13 C -0.0903(3) 0.1919(5) 0.8011(2) 0.0595(11) Uani 1 1 d . . . H13A H -0.0177 0.1889 0.7798 0.071 Uiso 1 1 calc R . . H13B H -0.1082 0.2916 0.8116 0.071 Uiso 1 1 calc R . . C14 C -0.1638(5) 0.1334(6) 0.7290(3) 0.0898(17) Uani 1 1 d . . . H14B H -0.2365 0.1397 0.7498 0.108 Uiso 1 1 calc R . . H14A H -0.1581 0.1953 0.6777 0.108 Uiso 1 1 calc R . . C15 C -0.1449(5) -0.0085(7) 0.7019(4) 0.130(2) Uani 1 1 d . . . H15A H -0.1952 -0.0346 0.6569 0.194 Uiso 1 1 calc R . . H15C H -0.1524 -0.0718 0.7515 0.194 Uiso 1 1 calc R . . H15B H -0.0741 -0.0161 0.6790 0.194 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 I1 0.0541(2) 0.0593(2) 0.04940(17) -0.01226(11) -0.00355(12) -0.01046(12) O1 0.0450(18) 0.101(2) 0.092(2) -0.0189(19) 0.0155(15) 0.0047(17) O2 0.0444(19) 0.095(2) 0.126(3) -0.039(2) -0.0042(18) -0.0142(17) O3 0.072(2) 0.0682(18) 0.0685(17) -0.0312(16) 0.0074(15) -0.0007(16) O4 0.0515(19) 0.0735(18) 0.0544(15) -0.0167(13) 0.0001(13) -0.0169(15) N1 0.042(2) 0.065(2) 0.065(2) 0.0039(18) 0.0032(17) -0.0004(18) N2 0.054(2) 0.0486(19) 0.0383(15) -0.0054(14) 0.0062(14) -0.0091(16) N3 0.0366(17) 0.0425(15) 0.0392(14) -0.0066(12) 0.0007(12) -0.0022(13) N4 0.0388(18) 0.0434(16) 0.0343(14) -0.0007(12) 0.0017(12) -0.0002(13) C1 0.033(2) 0.046(2) 0.050(2) 0.0018(16) 0.0018(15) 0.0012(16) C2 0.045(2) 0.0390(18) 0.0419(18) 0.0008(15) 0.0064(15) 0.0029(16) C3 0.041(2) 0.0354(17) 0.0361(16) 0.0033(14) 0.0013(14) -0.0026(15) C4 0.037(2) 0.0356(17) 0.0361(16) 0.0052(14) -0.0015(14) -0.0035(15) C5 0.043(2) 0.043(2) 0.0409(18) -0.0083(15) -0.0013(16) 0.0052(16) C6 0.043(2) 0.046(2) 0.053(2) -0.0072(17) -0.0054(17) 0.0000(17) C7 0.037(2) 0.0355(17) 0.0368(17) 0.0037(14) 0.0047(14) -0.0017(15) C8 0.039(2) 0.0411(19) 0.0378(16) -0.0014(15) 0.0025(14) -0.0044(16) C9 0.052(3) 0.046(2) 0.0433(19) -0.0081(16) 0.0012(17) 0.0003(18) C10 0.054(3) 0.055(2) 0.068(2) -0.012(2) 0.006(2) 0.005(2) C11 0.061(3) 0.090(3) 0.088(3) -0.022(3) 0.005(2) 0.026(3) C12 0.038(2) 0.0454(19) 0.0427(18) -0.0054(15) 0.0017(15) -0.0046(16) C13 0.064(3) 0.070(3) 0.045(2) -0.0013(19) -0.0129(19) -0.007(2) C14 0.088(4) 0.129(5) 0.052(2) -0.012(3) -0.013(2) -0.033(3) C15 0.134(6) 0.137(6) 0.117(5) -0.051(4) -0.019(4) -0.022(5) _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 C8 2.106(3) . ? O1 N1 1.221(4) . ? O2 N1 1.207(4) . ? O3 N2 1.225(4) . ? O4 N2 1.232(4) . ? N1 C1 1.459(4) . ? N2 C3 1.448(4) . ? N3 C4 1.339(4) . ? N3 N4 1.374(4) . ? N3 H3 0.8600 . ? N4 C7 1.283(4) . ? C1 C2 1.368(5) . ? C1 C6 1.386(5) . ? C2 C3 1.369(5) . ? C2 H2 0.9300 . ? C3 C4 1.418(5) . ? C4 C5 1.409(5) . ? C5 C6 1.350(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.471(5) . ? C7 C12 1.509(5) . ? C8 C9 1.318(5) . ? C9 C10 1.490(5) . ? C9 H9 0.9300 . ? C10 C11 1.511(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11C 0.9600 . ? C11 H11B 0.9600 . ? C12 C13 1.520(5) . ? C12 H12B 0.9700 . ? C12 H12A 0.9700 . ? C13 C14 1.528(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.406(7) . ? C14 H14B 0.9700 . ? C14 H14A 0.9700 . ? C15 H15A 0.9600 . ? C15 H15C 0.9600 . ? C15 H15B 0.9600 . ? 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 O2 N1 O1 124.0(4) . . ? O2 N1 C1 117.8(3) . . ? O1 N1 C1 118.1(3) . . ? O3 N2 O4 121.9(3) . . ? O3 N2 C3 118.6(3) . . ? O4 N2 C3 119.5(3) . . ? C4 N3 N4 119.0(3) . . ? C4 N3 H3 120.5 . . ? N4 N3 H3 120.5 . . ? C7 N4 N3 117.9(3) . . ? C2 C1 C6 121.1(3) . . ? C2 C1 N1 118.9(3) . . ? C6 C1 N1 120.0(3) . . ? C1 C2 C3 118.8(3) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C2 C3 C4 122.1(3) . . ? C2 C3 N2 116.0(3) . . ? C4 C3 N2 121.8(3) . . ? N3 C4 C5 120.7(3) . . ? N3 C4 C3 123.2(3) . . ? C5 C4 C3 116.2(3) . . ? C6 C5 C4 121.5(3) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C1 120.2(3) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? N4 C7 C8 115.7(3) . . ? N4 C7 C12 124.2(3) . . ? C8 C7 C12 120.0(3) . . ? C9 C8 C7 125.1(3) . . ? C9 C8 I1 118.8(2) . . ? C7 C8 I1 116.0(2) . . ? C8 C9 C10 128.4(3) . . ? C8 C9 H9 115.8 . . ? C10 C9 H9 115.8 . . ? C9 C10 C11 114.3(3) . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? H11C C11 H11B 109.5 . . ? C7 C12 C13 111.8(3) . . ? C7 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? C7 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? H12B C12 H12A 107.9 . . ? C12 C13 C14 114.5(4) . . ? C12 C13 H13A 108.6 . . ? C14 C13 H13A 108.6 . . ? C12 C13 H13B 108.6 . . ? C14 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? C15 C14 C13 116.2(5) . . ? C15 C14 H14B 108.2 . . ? C13 C14 H14B 108.2 . . ? C15 C14 H14A 108.2 . . ? C13 C14 H14A 108.2 . . ? H14B C14 H14A 107.4 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? H15C C15 H15B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.686 _refine_diff_density_min -0.619 _refine_diff_density_rms 0.096 data_cd211398 _database_code_depnum_ccdc_archive 'CCDC 877901' #TrackingRef '- 4l.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H15 I N4 O4' _chemical_formula_weight 466.23 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1296(10) _cell_length_b 7.4865(10) _cell_length_c 17.896(3) _cell_angle_alpha 87.393(2) _cell_angle_beta 84.501(2) _cell_angle_gamma 71.105(2) _cell_volume 899.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2415 _cell_measurement_theta_min 4.574 _cell_measurement_theta_max 56.376 _exptl_crystal_description prismatic _exptl_crystal_colour red _exptl_crystal_size_max 0.213 _exptl_crystal_size_mid 0.097 _exptl_crystal_size_min 0.085 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.721 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 1.811 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.62583 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4891 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3458 _reflns_number_gt 3069 _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^)+(0.0412P)^2^+0.2307P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3458 _refine_ls_number_parameters 239 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.038 _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 0.76257(3) 0.84894(3) 0.674279(11) 0.05912(11) Uani 1 1 d . . . N1 N 0.5339(3) 0.7405(3) 0.81837(13) 0.0445(5) Uani 1 1 d . . . N2 N 0.4075(4) 0.7148(4) 0.87772(14) 0.0450(6) Uani 1 1 d D . . N3 N 0.1202(3) 0.6694(3) 0.99928(13) 0.0440(5) Uani 1 1 d . . . N4 N -0.3971(4) 1.1468(4) 0.87889(16) 0.0539(6) Uani 1 1 d . . . O1 O 0.2962(3) 0.5731(4) 1.00392(13) 0.0624(6) Uani 1 1 d . . . O2 O -0.0095(3) 0.6610(3) 1.04792(12) 0.0578(6) Uani 1 1 d . . . O3 O -0.5182(4) 1.1048(4) 0.92236(17) 0.0833(8) Uani 1 1 d . . . O4 O -0.4415(4) 1.2790(4) 0.83391(16) 0.0746(7) Uani 1 1 d . . . C1 C 0.7143(4) 0.6376(4) 0.81888(15) 0.0434(7) Uani 1 1 d . . . H1A H 0.7521 0.5531 0.8587 0.052 Uiso 1 1 calc R . . C2 C 0.8627(4) 0.6478(4) 0.75931(15) 0.0418(6) Uani 1 1 d . . . C3 C 1.0519(4) 0.5393(4) 0.76016(18) 0.0486(7) Uani 1 1 d . . . H3A H 1.0812 0.4586 0.8016 0.058 Uiso 1 1 calc R . . C4 C 1.2232(4) 0.5292(4) 0.70386(19) 0.0548(8) Uani 1 1 d . . . H4A H 1.3204 0.5693 0.7268 0.066 Uiso 1 1 calc R . . H4B H 1.1769 0.6150 0.6623 0.066 Uiso 1 1 calc R . . C5 C 1.3216(5) 0.3301(5) 0.67427(19) 0.0569(8) Uani 1 1 d . . . H5A H 1.3687 0.2455 0.7161 0.068 Uiso 1 1 calc R . . H5B H 1.2226 0.2898 0.6526 0.068 Uiso 1 1 calc R . . C6 C 1.4933(4) 0.3125(4) 0.61619(17) 0.0496(7) Uani 1 1 d . . . C7 C 1.6527(5) 0.3663(5) 0.6314(2) 0.0637(9) Uani 1 1 d . . . H7 H 1.6519 0.4192 0.6775 0.076 Uiso 1 1 calc R . . C8 C 1.8133(6) 0.3428(7) 0.5792(3) 0.0826(12) Uani 1 1 d . . . H8 H 1.9190 0.3812 0.5904 0.099 Uiso 1 1 calc R . . C9 C 1.8200(7) 0.2645(7) 0.5118(3) 0.0925(15) Uani 1 1 d . . . H9 H 1.9309 0.2454 0.4775 0.111 Uiso 1 1 calc R . . C10 C 1.6622(9) 0.2144(7) 0.4952(2) 0.0976(16) Uani 1 1 d . . . H10 H 1.6637 0.1640 0.4486 0.117 Uiso 1 1 calc R . . C11 C 1.5001(6) 0.2372(5) 0.5466(2) 0.0711(10) Uani 1 1 d . . . H11 H 1.3936 0.2014 0.5343 0.085 Uiso 1 1 calc R . . C12 C 0.2133(4) 0.8186(4) 0.88015(16) 0.0396(6) Uani 1 1 d . . . C13 C 0.0686(4) 0.7974(4) 0.93686(15) 0.0389(6) Uani 1 1 d . . . C14 C -0.1313(4) 0.9044(4) 0.93562(15) 0.0407(6) Uani 1 1 d . . . H14 H -0.2248 0.8872 0.9727 0.049 Uiso 1 1 calc R . . C15 C -0.1886(4) 1.0347(4) 0.87960(16) 0.0435(6) Uani 1 1 d . . . C16 C -0.0499(5) 1.0619(4) 0.82313(18) 0.0475(7) Uani 1 1 d . . . H16 H -0.0912 1.1519 0.7854 0.057 Uiso 1 1 calc R . . C17 C 0.1445(4) 0.9568(4) 0.82354(17) 0.0475(7) Uani 1 1 d . . . H17 H 0.2352 0.9759 0.7857 0.057 Uiso 1 1 calc R . . H2 H 0.448(6) 0.632(4) 0.9087(17) 0.069(12) 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 0.05253(15) 0.05758(16) 0.05119(15) 0.01216(10) 0.00879(10) -0.00105(10) N1 0.0357(13) 0.0492(13) 0.0435(13) -0.0014(11) 0.0101(10) -0.0102(10) N2 0.0355(13) 0.0496(14) 0.0428(14) 0.0040(11) 0.0086(10) -0.0079(11) N3 0.0376(13) 0.0541(14) 0.0380(12) -0.0015(11) 0.0039(10) -0.0134(11) N4 0.0401(14) 0.0527(15) 0.0612(17) -0.0026(13) -0.0021(12) -0.0046(12) O1 0.0340(11) 0.0798(16) 0.0582(14) 0.0233(12) 0.0012(9) -0.0022(10) O2 0.0431(12) 0.0756(15) 0.0460(12) 0.0086(11) 0.0100(9) -0.0123(11) O3 0.0381(13) 0.100(2) 0.092(2) 0.0225(16) 0.0105(13) -0.0023(13) O4 0.0538(15) 0.0687(16) 0.0856(19) 0.0155(14) -0.0083(13) 0.0002(12) C1 0.0395(16) 0.0457(16) 0.0414(16) 0.0003(13) 0.0028(12) -0.0107(13) C2 0.0386(15) 0.0408(14) 0.0400(15) 0.0002(11) 0.0064(11) -0.0071(11) C3 0.0411(16) 0.0497(17) 0.0487(17) 0.0041(13) 0.0075(13) -0.0100(13) C4 0.0372(16) 0.0521(17) 0.063(2) 0.0028(15) 0.0133(14) -0.0031(13) C5 0.0473(17) 0.0598(19) 0.060(2) -0.0062(16) 0.0062(14) -0.0145(14) C6 0.0451(17) 0.0433(16) 0.0494(17) 0.0009(13) 0.0031(13) -0.0011(13) C7 0.0449(18) 0.086(2) 0.055(2) -0.0035(18) 0.0040(15) -0.0152(17) C8 0.050(2) 0.104(3) 0.081(3) 0.011(2) 0.0133(19) -0.014(2) C9 0.082(3) 0.088(3) 0.077(3) 0.010(2) 0.038(2) 0.002(2) C10 0.132(5) 0.088(3) 0.054(2) -0.014(2) 0.025(3) -0.017(3) C11 0.080(3) 0.071(2) 0.059(2) -0.0088(18) -0.0003(19) -0.021(2) C12 0.0335(14) 0.0433(15) 0.0404(15) -0.0058(12) 0.0044(11) -0.0117(11) C13 0.0340(14) 0.0421(14) 0.0380(14) -0.0028(11) -0.0002(11) -0.0093(11) C14 0.0342(14) 0.0460(15) 0.0412(15) -0.0067(12) 0.0040(11) -0.0133(12) C15 0.0352(14) 0.0426(15) 0.0478(16) -0.0050(13) -0.0002(12) -0.0062(12) C16 0.0446(16) 0.0432(15) 0.0501(17) 0.0050(13) -0.0026(13) -0.0090(13) C17 0.0407(16) 0.0499(16) 0.0482(17) 0.0035(13) 0.0069(12) -0.0129(13) _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 C2 2.097(3) . ? N1 C1 1.268(3) . ? N1 N2 1.374(3) . ? N2 C12 1.348(4) . ? N2 H2 0.813(18) . ? N3 O2 1.223(3) . ? N3 O1 1.237(3) . ? N3 C13 1.433(4) . ? N4 O3 1.214(4) . ? N4 O4 1.225(3) . ? N4 C15 1.453(4) . ? C1 C2 1.446(4) . ? C1 H1A 0.9300 . ? C2 C3 1.331(4) . ? C3 C4 1.491(4) . ? C3 H3A 0.9300 . ? C4 C5 1.522(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.503(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.376(5) . ? C6 C11 1.380(5) . ? C7 C8 1.376(5) . ? C7 H7 0.9300 . ? C8 C9 1.354(7) . ? C8 H8 0.9300 . ? C9 C10 1.357(7) . ? C9 H9 0.9300 . ? C10 C11 1.376(6) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C17 1.417(4) . ? C12 C13 1.418(4) . ? C13 C14 1.392(4) . ? C14 C15 1.362(4) . ? C14 H14 0.9300 . ? C15 C16 1.400(4) . ? C16 C17 1.355(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? 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 C1 N1 N2 116.0(2) . . ? C12 N2 N1 118.9(2) . . ? C12 N2 H2 121(3) . . ? N1 N2 H2 120(3) . . ? O2 N3 O1 121.2(2) . . ? O2 N3 C13 119.5(2) . . ? O1 N3 C13 119.3(2) . . ? O3 N4 O4 123.5(3) . . ? O3 N4 C15 118.7(3) . . ? O4 N4 C15 117.9(3) . . ? N1 C1 C2 121.8(3) . . ? N1 C1 H1A 119.1 . . ? C2 C1 H1A 119.1 . . ? C3 C2 C1 121.5(3) . . ? C3 C2 I1 122.6(2) . . ? C1 C2 I1 115.80(19) . . ? C2 C3 C4 128.9(3) . . ? C2 C3 H3A 115.5 . . ? C4 C3 H3A 115.5 . . ? C3 C4 C5 111.6(3) . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C6 C5 C4 113.9(3) . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5B 108.8 . . ? C4 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C7 C6 C11 117.4(3) . . ? C7 C6 C5 121.0(3) . . ? C11 C6 C5 121.6(3) . . ? C8 C7 C6 120.8(4) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C9 C8 C7 121.1(4) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 118.9(4) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C9 C10 C11 120.9(4) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C6 120.8(4) . . ? C10 C11 H11 119.6 . . ? C6 C11 H11 119.6 . . ? N2 C12 C17 119.8(3) . . ? N2 C12 C13 123.6(3) . . ? C17 C12 C13 116.6(2) . . ? C14 C13 C12 121.3(3) . . ? C14 C13 N3 116.5(2) . . ? C12 C13 N3 122.1(2) . . ? C15 C14 C13 119.4(3) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 121.1(3) . . ? C14 C15 N4 119.1(3) . . ? C16 C15 N4 119.8(3) . . ? C17 C16 C15 119.9(3) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C12 121.7(3) . . ? C16 C17 H17 119.1 . . ? C12 C17 H17 119.1 . . ? 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 C1 N1 N2 C12 -179.3(3) . . . . ? N2 N1 C1 C2 179.0(3) . . . . ? N1 C1 C2 C3 -180.0(3) . . . . ? N1 C1 C2 I1 1.9(4) . . . . ? C1 C2 C3 C4 179.3(3) . . . . ? I1 C2 C3 C4 -2.6(5) . . . . ? C2 C3 C4 C5 -122.9(4) . . . . ? C3 C4 C5 C6 179.0(3) . . . . ? C4 C5 C6 C7 56.4(4) . . . . ? C4 C5 C6 C11 -125.4(4) . . . . ? C11 C6 C7 C8 -0.9(5) . . . . ? C5 C6 C7 C8 177.3(3) . . . . ? C6 C7 C8 C9 -0.6(6) . . . . ? C7 C8 C9 C10 2.0(7) . . . . ? C8 C9 C10 C11 -1.9(8) . . . . ? C9 C10 C11 C6 0.3(7) . . . . ? C7 C6 C11 C10 1.1(6) . . . . ? C5 C6 C11 C10 -177.1(4) . . . . ? N1 N2 C12 C17 -2.5(4) . . . . ? N1 N2 C12 C13 177.0(3) . . . . ? N2 C12 C13 C14 -178.1(3) . . . . ? C17 C12 C13 C14 1.4(4) . . . . ? N2 C12 C13 N3 3.6(4) . . . . ? C17 C12 C13 N3 -176.8(2) . . . . ? O2 N3 C13 C14 -0.7(4) . . . . ? O1 N3 C13 C14 -178.8(3) . . . . ? O2 N3 C13 C12 177.6(3) . . . . ? O1 N3 C13 C12 -0.5(4) . . . . ? C12 C13 C14 C15 -1.2(4) . . . . ? N3 C13 C14 C15 177.1(2) . . . . ? C13 C14 C15 C16 0.3(4) . . . . ? C13 C14 C15 N4 -179.6(2) . . . . ? O3 N4 C15 C14 -9.5(4) . . . . ? O4 N4 C15 C14 170.8(3) . . . . ? O3 N4 C15 C16 170.6(3) . . . . ? O4 N4 C15 C16 -9.1(4) . . . . ? C14 C15 C16 C17 0.4(5) . . . . ? N4 C15 C16 C17 -179.7(3) . . . . ? C15 C16 C17 C12 -0.2(5) . . . . ? N2 C12 C17 C16 178.9(3) . . . . ? C13 C12 C17 C16 -0.7(4) . . . . ? 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 N2 H2 O1 0.813(18) 2.58(2) 3.330(3) 155(4) 2_667 N2 H2 O1 0.813(18) 2.04(3) 2.616(3) 127(4) . _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.780 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.066