# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_cvd163 #TrackingRef 'In_Guanidinates.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H72 In N9' _chemical_formula_weight 709.82 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' In In -0.7276 1.3100 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.4523(3) _cell_length_b 12.8122(14) _cell_length_c 19.7849(15) _cell_angle_alpha 90.00 _cell_angle_beta 98.503(6) _cell_angle_gamma 90.00 _cell_volume 4124.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 111(2) _cell_measurement_reflns_used 1500 _cell_measurement_theta_min 2.663 _cell_measurement_theta_max 27.499 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.143 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 0.604 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 111(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Sapphire2-CCD, Oxford Diffraction' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32012 _diffrn_reflns_av_R_equivalents 0.0959 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3638 _reflns_number_gt 3120 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD 1.171.13, Oxford Diffraction' _computing_cell_refinement 'CrysAlis RED 1.171.13, Oxford Diffraction' _computing_data_reduction 'CrysAlis RED 1.171.13, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXS-97 _computing_publication_material SHELXS-97 _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^)+(0.0396P)^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 3638 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0384 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0690 _refine_ls_wR_factor_gt 0.0670 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 In1 In 0.0000 0.191878(17) 0.2500 0.02043(9) Uani 1 2 d S . . N4 N 0.05036(10) 0.03851(13) 0.21746(9) 0.0211(4) Uani 1 1 d . . . N1 N -0.02506(10) 0.29659(14) 0.33705(10) 0.0231(4) Uani 1 1 d . . . N3 N 0.07947(10) 0.35195(15) 0.42715(10) 0.0257(4) Uani 1 1 d . . . N6 N 0.0000 -0.1270(2) 0.2500 0.0313(7) Uani 1 2 d S . . N2 N 0.10265(10) 0.23864(14) 0.33364(9) 0.0212(4) Uani 1 1 d . . . C1 C 0.05339(12) 0.29571(15) 0.36675(12) 0.0212(5) Uani 1 1 d . . . C12 C 0.18186(12) 0.19574(17) 0.36684(12) 0.0249(5) Uani 1 1 d . . . H2A H 0.1968 0.2303 0.4123 0.030 Uiso 1 1 calc R . . C3 C 0.24833(14) 0.2204(2) 0.32274(14) 0.0370(6) Uani 1 1 d . . . H3A H 0.2514 0.2961 0.3163 0.055 Uiso 1 1 calc R . . H3B H 0.2347 0.1863 0.2782 0.055 Uiso 1 1 calc R . . H3C H 0.3015 0.1947 0.3455 0.055 Uiso 1 1 calc R . . C4 C 0.17643(14) 0.07884(19) 0.37794(13) 0.0361(6) Uani 1 1 d . . . H4A H 0.1339 0.0643 0.4065 0.054 Uiso 1 1 calc R . . H4B H 0.2295 0.0529 0.4007 0.054 Uiso 1 1 calc R . . H4C H 0.1623 0.0438 0.3337 0.054 Uiso 1 1 calc R . . C5 C 0.15650(14) 0.41015(18) 0.43560(13) 0.0331(6) Uani 1 1 d . . . H5A H 0.1804 0.4067 0.3926 0.040 Uiso 1 1 calc R . . H5B H 0.1958 0.3770 0.4720 0.040 Uiso 1 1 calc R . . C6 C 0.14532(17) 0.5233(2) 0.45391(17) 0.0501(8) Uani 1 1 d . . . H6A H 0.1986 0.5589 0.4593 0.075 Uiso 1 1 calc R . . H6B H 0.1225 0.5273 0.4969 0.075 Uiso 1 1 calc R . . H6C H 0.1076 0.5571 0.4175 0.075 Uiso 1 1 calc R . . C7 C 0.04462(14) 0.3248(2) 0.48888(13) 0.0347(6) Uani 1 1 d . . . H7A H -0.0144 0.3081 0.4759 0.042 Uiso 1 1 calc R . . H7B H 0.0486 0.3862 0.5196 0.042 Uiso 1 1 calc R . . C8 C 0.08735(18) 0.2323(3) 0.52783(15) 0.0544(8) Uani 1 1 d . . . H8A H 0.0615 0.2182 0.5684 0.082 Uiso 1 1 calc R . . H8B H 0.1456 0.2488 0.5418 0.082 Uiso 1 1 calc R . . H8C H 0.0824 0.1706 0.4982 0.082 Uiso 1 1 calc R . . C9 C -0.08266(12) 0.37904(17) 0.35080(13) 0.0273(5) Uani 1 1 d . . . H9A H -0.0576 0.4185 0.3923 0.033 Uiso 1 1 calc R . . C10 C -0.16308(15) 0.3297(2) 0.36539(17) 0.0457(8) Uani 1 1 d . . . H10A H -0.1515 0.2818 0.4042 0.069 Uiso 1 1 calc R . . H10B H -0.1887 0.2911 0.3250 0.069 Uiso 1 1 calc R . . H10C H -0.2005 0.3847 0.3763 0.069 Uiso 1 1 calc R . . C11 C -0.09837(16) 0.4551(2) 0.29113(15) 0.0450(7) Uani 1 1 d . . . H11A H -0.0462 0.4861 0.2831 0.068 Uiso 1 1 calc R . . H11B H -0.1356 0.5103 0.3019 0.068 Uiso 1 1 calc R . . H11C H -0.1234 0.4177 0.2500 0.068 Uiso 1 1 calc R . . C2 C 0.0000 -0.0174(2) 0.2500 0.0253(7) Uani 1 2 d S . . C13 C 0.08859(13) -0.00257(17) 0.16044(12) 0.0254(5) Uani 1 1 d . . . H13A H 0.0813 -0.0801 0.1588 0.030 Uiso 1 1 calc R . . C14 C 0.04905(15) 0.0427(2) 0.09265(13) 0.0384(6) Uani 1 1 d . . . H14A H -0.0099 0.0269 0.0856 0.058 Uiso 1 1 calc R . . H14B H 0.0745 0.0119 0.0556 0.058 Uiso 1 1 calc R . . H14C H 0.0570 0.1185 0.0930 0.058 Uiso 1 1 calc R . . C15 C 0.18096(13) 0.0217(2) 0.17205(14) 0.0370(6) Uani 1 1 d . . . H15A H 0.2063 -0.0088 0.2156 0.055 Uiso 1 1 calc R . . H15B H 0.1891 0.0974 0.1733 0.055 Uiso 1 1 calc R . . H15C H 0.2065 -0.0082 0.1347 0.055 Uiso 1 1 calc R . . C16 C 0.07678(15) -0.18529(19) 0.26561(16) 0.0417(7) Uani 1 1 d . . . H16A H 0.1235 -0.1367 0.2655 0.050 Uiso 1 1 calc R . . H16B H 0.0796 -0.2377 0.2292 0.050 Uiso 1 1 calc R . . C17 C 0.0853(2) -0.2401(4) 0.3336(2) 0.1060(17) Uani 1 1 d . . . H17A H 0.1379 -0.2773 0.3415 0.159 Uiso 1 1 calc R . . H17B H 0.0401 -0.2900 0.3336 0.159 Uiso 1 1 calc R . . H17C H 0.0834 -0.1886 0.3700 0.159 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 In1 0.01589(13) 0.02005(13) 0.02600(14) 0.000 0.00527(9) 0.000 N4 0.0183(9) 0.0215(9) 0.0247(10) 0.0005(8) 0.0075(8) 0.0012(7) N1 0.0158(9) 0.0251(10) 0.0285(11) -0.0027(8) 0.0035(8) 0.0032(7) N3 0.0214(10) 0.0312(10) 0.0254(11) -0.0045(9) 0.0068(8) -0.0035(8) N6 0.0246(14) 0.0168(14) 0.055(2) 0.000 0.0124(13) 0.000 N2 0.0174(9) 0.0193(9) 0.0269(10) -0.0028(8) 0.0038(8) 0.0014(7) C1 0.0231(11) 0.0157(11) 0.0255(12) 0.0006(9) 0.0063(9) -0.0015(9) C12 0.0163(10) 0.0291(12) 0.0283(13) -0.0046(11) 0.0001(9) 0.0033(10) C3 0.0201(12) 0.0433(15) 0.0482(17) -0.0072(13) 0.0072(11) 0.0026(10) C4 0.0287(13) 0.0331(13) 0.0445(16) 0.0016(13) -0.0016(11) 0.0083(11) C5 0.0290(13) 0.0327(14) 0.0390(15) -0.0105(12) 0.0097(11) -0.0064(10) C6 0.0509(17) 0.0341(15) 0.070(2) -0.0130(15) 0.0230(15) -0.0099(13) C7 0.0349(14) 0.0411(15) 0.0308(14) -0.0080(12) 0.0135(11) -0.0059(11) C8 0.0513(18) 0.073(2) 0.0384(17) 0.0112(16) 0.0045(14) -0.0061(16) C9 0.0205(12) 0.0245(12) 0.0377(14) -0.0093(11) 0.0070(10) 0.0035(9) C10 0.0248(13) 0.0405(16) 0.076(2) -0.0157(15) 0.0204(13) 0.0024(11) C11 0.0438(16) 0.0394(16) 0.0521(18) 0.0015(14) 0.0082(13) 0.0196(12) C2 0.0183(16) 0.0261(17) 0.0311(19) 0.000 0.0019(14) 0.000 C13 0.0269(12) 0.0216(12) 0.0300(14) -0.0035(10) 0.0117(10) 0.0005(9) C14 0.0407(15) 0.0465(16) 0.0293(15) -0.0040(12) 0.0097(11) 0.0081(12) C15 0.0274(13) 0.0404(15) 0.0470(17) -0.0041(13) 0.0186(12) 0.0032(11) C16 0.0364(14) 0.0232(13) 0.070(2) 0.0077(14) 0.0216(13) 0.0078(11) C17 0.056(2) 0.128(4) 0.138(4) 0.098(3) 0.029(2) 0.027(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 In1 N4 2.2627(17) 2 ? In1 N4 2.2627(17) . ? In1 N2 2.2634(17) . ? In1 N2 2.2634(17) 2 ? In1 N1 2.2685(18) . ? In1 N1 2.2685(18) 2 ? In1 C2 2.681(3) . ? In1 C1 2.698(2) . ? In1 C1 2.698(2) 2 ? N4 C2 1.331(2) . ? N4 C13 1.468(3) . ? N1 C1 1.337(3) . ? N1 C9 1.471(3) . ? N3 C1 1.407(3) . ? N3 C5 1.459(3) . ? N3 C7 1.466(3) . ? N6 C2 1.404(4) . ? N6 C16 1.461(3) 2 ? N6 C16 1.461(3) . ? N2 C1 1.333(3) . ? N2 C12 1.476(3) . ? C12 C4 1.518(3) . ? C12 C3 1.529(3) . ? C12 H2A 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.512(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.527(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C11 1.523(4) . ? C9 C10 1.532(3) . ? C9 H9A 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C2 N4 1.331(2) 2 ? C13 C14 1.516(3) . ? C13 C15 1.535(3) . ? C13 H13A 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.506(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? 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 N4 In1 N4 59.45(9) 2 . ? N4 In1 N2 106.67(6) 2 . ? N4 In1 N2 99.95(6) . . ? N4 In1 N2 99.95(6) 2 2 ? N4 In1 N2 106.67(6) . 2 ? N2 In1 N2 149.31(9) . 2 ? N4 In1 N1 100.50(6) 2 . ? N4 In1 N1 147.66(7) . . ? N2 In1 N1 59.21(6) . . ? N2 In1 N1 101.47(6) 2 . ? N4 In1 N1 147.66(7) 2 2 ? N4 In1 N1 100.50(6) . 2 ? N2 In1 N1 101.47(6) . 2 ? N2 In1 N1 59.21(6) 2 2 ? N1 In1 N1 107.49(9) . 2 ? N4 In1 C2 29.72(4) 2 . ? N4 In1 C2 29.72(4) . . ? N2 In1 C2 105.35(5) . . ? N2 In1 C2 105.35(5) 2 . ? N1 In1 C2 126.26(5) . . ? N1 In1 C2 126.26(5) 2 . ? N4 In1 C1 105.74(6) 2 . ? N4 In1 C1 125.83(6) . . ? N2 In1 C1 29.56(6) . . ? N2 In1 C1 127.50(6) 2 . ? N1 In1 C1 29.66(6) . . ? N1 In1 C1 106.60(6) 2 . ? C2 In1 C1 119.55(4) . . ? N4 In1 C1 125.83(6) 2 2 ? N4 In1 C1 105.74(6) . 2 ? N2 In1 C1 127.50(6) . 2 ? N2 In1 C1 29.56(6) 2 2 ? N1 In1 C1 106.60(6) . 2 ? N1 In1 C1 29.66(6) 2 2 ? C2 In1 C1 119.55(4) . 2 ? C1 In1 C1 120.90(9) . 2 ? C2 N4 C13 123.15(18) . . ? C2 N4 In1 92.83(14) . . ? C13 N4 In1 138.28(14) . . ? C1 N1 C9 122.08(18) . . ? C1 N1 In1 93.25(13) . . ? C9 N1 In1 139.42(14) . . ? C1 N3 C5 120.65(18) . . ? C1 N3 C7 118.59(18) . . ? C5 N3 C7 117.78(19) . . ? C2 N6 C16 120.77(14) . 2 ? C2 N6 C16 120.77(14) . . ? C16 N6 C16 118.5(3) 2 . ? C1 N2 C12 123.12(19) . . ? C1 N2 In1 93.57(12) . . ? C12 N2 In1 137.82(14) . . ? N2 C1 N1 113.96(19) . . ? N2 C1 N3 124.54(19) . . ? N1 C1 N3 121.49(18) . . ? N2 C1 In1 56.87(11) . . ? N1 C1 In1 57.10(11) . . ? N3 C1 In1 178.39(15) . . ? N2 C12 C4 111.39(17) . . ? N2 C12 C3 109.14(19) . . ? C4 C12 C3 110.4(2) . . ? N2 C12 H2A 108.6 . . ? C4 C12 H2A 108.6 . . ? C3 C12 H2A 108.6 . . ? C12 C3 H3A 109.5 . . ? C12 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C12 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C12 C4 H4A 109.5 . . ? C12 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C12 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 C6 112.53(19) . . ? N3 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? N3 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 C8 113.4(2) . . ? N3 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? N3 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 C11 110.85(19) . . ? N1 C9 C10 109.67(18) . . ? C11 C9 C10 111.0(2) . . ? N1 C9 H9A 108.4 . . ? C11 C9 H9A 108.4 . . ? C10 C9 H9A 108.4 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N4 C2 N4 114.9(3) 2 . ? N4 C2 N6 122.56(14) 2 . ? N4 C2 N6 122.56(14) . . ? N4 C2 In1 57.44(14) 2 . ? N4 C2 In1 57.44(14) . . ? N6 C2 In1 180.0 . . ? N4 C13 C14 111.48(18) . . ? N4 C13 C15 109.87(18) . . ? C14 C13 C15 109.9(2) . . ? N4 C13 H13A 108.5 . . ? C14 C13 H13A 108.5 . . ? C15 C13 H13A 108.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N6 C16 C17 113.0(2) . . ? N6 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? N6 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? 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 N4 In1 N4 C2 0.0 2 . . . ? N2 In1 N4 C2 103.57(9) . . . . ? N2 In1 N4 C2 -91.88(9) 2 . . . ? N1 In1 N4 C2 57.54(15) . . . . ? N1 In1 N4 C2 -152.68(8) 2 . . . ? C1 In1 N4 C2 87.84(10) . . . . ? C1 In1 N4 C2 -122.67(8) 2 . . . ? N4 In1 N4 C13 151.4(3) 2 . . . ? N2 In1 N4 C13 -105.0(2) . . . . ? N2 In1 N4 C13 59.6(2) 2 . . . ? N1 In1 N4 C13 -151.02(18) . . . . ? N1 In1 N4 C13 -1.2(2) 2 . . . ? C2 In1 N4 C13 151.4(3) . . . . ? C1 In1 N4 C13 -120.72(19) . . . . ? C1 In1 N4 C13 28.8(2) 2 . . . ? N4 In1 N1 C1 103.41(13) 2 . . . ? N4 In1 N1 C1 55.76(18) . . . . ? N2 In1 N1 C1 0.16(11) . . . . ? N2 In1 N1 C1 -154.06(12) 2 . . . ? N1 In1 N1 C1 -92.99(12) 2 . . . ? C2 In1 N1 C1 87.01(12) . . . . ? C1 In1 N1 C1 -124.02(13) 2 . . . ? N4 In1 N1 C9 -104.4(2) 2 . . . ? N4 In1 N1 C9 -152.09(19) . . . . ? N2 In1 N1 C9 152.3(2) . . . . ? N2 In1 N1 C9 -1.9(2) 2 . . . ? N1 In1 N1 C9 59.2(2) 2 . . . ? C2 In1 N1 C9 -120.8(2) . . . . ? C1 In1 N1 C9 152.1(3) . . . . ? C1 In1 N1 C9 28.1(2) 2 . . . ? N4 In1 N2 C1 -92.63(13) 2 . . . ? N4 In1 N2 C1 -153.54(12) . . . . ? N2 In1 N2 C1 56.45(12) 2 . . . ? N1 In1 N2 C1 -0.16(12) . . . . ? N1 In1 N2 C1 103.49(13) 2 . . . ? C2 In1 N2 C1 -123.55(12) . . . . ? C1 In1 N2 C1 87.66(16) 2 . . . ? N4 In1 N2 C12 59.5(2) 2 . . . ? N4 In1 N2 C12 -1.4(2) . . . . ? N2 In1 N2 C12 -151.4(2) 2 . . . ? N1 In1 N2 C12 152.0(2) . . . . ? N1 In1 N2 C12 -104.4(2) 2 . . . ? C2 In1 N2 C12 28.6(2) . . . . ? C1 In1 N2 C12 152.2(3) . . . . ? C1 In1 N2 C12 -120.2(2) 2 . . . ? C12 N2 C1 N1 -157.75(19) . . . . ? In1 N2 C1 N1 0.26(18) . . . . ? C12 N2 C1 N3 22.9(3) . . . . ? In1 N2 C1 N3 -179.06(19) . . . . ? C12 N2 C1 In1 -158.0(2) . . . . ? C9 N1 C1 N2 -159.2(2) . . . . ? In1 N1 C1 N2 -0.26(18) . . . . ? C9 N1 C1 N3 20.1(3) . . . . ? In1 N1 C1 N3 179.08(18) . . . . ? C9 N1 C1 In1 -159.0(2) . . . . ? C5 N3 C1 N2 41.2(3) . . . . ? C7 N3 C1 N2 -118.8(2) . . . . ? C5 N3 C1 N1 -138.1(2) . . . . ? C7 N3 C1 N1 61.9(3) . . . . ? C5 N3 C1 In1 -109(6) . . . . ? C7 N3 C1 In1 90(6) . . . . ? N4 In1 C1 N2 96.16(13) 2 . . . ? N4 In1 C1 N2 32.77(15) . . . . ? N2 In1 C1 N2 -147.57(12) 2 . . . ? N1 In1 C1 N2 179.7(2) . . . . ? N1 In1 C1 N2 -83.96(13) 2 . . . ? C2 In1 C1 N2 67.49(13) . . . . ? C1 In1 C1 N2 -112.51(13) 2 . . . ? N4 In1 C1 N1 -83.56(13) 2 . . . ? N4 In1 C1 N1 -146.95(12) . . . . ? N2 In1 C1 N1 -179.7(2) . . . . ? N2 In1 C1 N1 32.71(15) 2 . . . ? N1 In1 C1 N1 96.32(14) 2 . . . ? C2 In1 C1 N1 -112.23(12) . . . . ? C1 In1 C1 N1 67.77(12) 2 . . . ? N4 In1 C1 N3 -113(6) 2 . . . ? N4 In1 C1 N3 -176(100) . . . . ? N2 In1 C1 N3 151(6) . . . . ? N2 In1 C1 N3 4(6) 2 . . . ? N1 In1 C1 N3 -29(6) . . . . ? N1 In1 C1 N3 67(6) 2 . . . ? C2 In1 C1 N3 -141(6) . . . . ? C1 In1 C1 N3 39(6) 2 . . . ? C1 N2 C12 C4 106.2(2) . . . . ? In1 N2 C12 C4 -40.0(3) . . . . ? C1 N2 C12 C3 -131.6(2) . . . . ? In1 N2 C12 C3 82.2(2) . . . . ? C1 N3 C5 C6 125.9(2) . . . . ? C7 N3 C5 C6 -73.9(3) . . . . ? C1 N3 C7 C8 83.0(3) . . . . ? C5 N3 C7 C8 -77.7(3) . . . . ? C1 N1 C9 C11 104.6(2) . . . . ? In1 N1 C9 C11 -42.0(3) . . . . ? C1 N1 C9 C10 -132.6(2) . . . . ? In1 N1 C9 C10 80.8(3) . . . . ? C13 N4 C2 N4 -157.7(2) . . . 2 ? In1 N4 C2 N4 0.0 . . . 2 ? C13 N4 C2 N6 22.3(2) . . . . ? In1 N4 C2 N6 180.0 . . . . ? C13 N4 C2 In1 -157.7(2) . . . . ? C16 N6 C2 N4 48.66(16) 2 . . 2 ? C16 N6 C2 N4 -131.34(16) . . . 2 ? C16 N6 C2 N4 -131.34(16) 2 . . . ? C16 N6 C2 N4 48.66(16) . . . . ? C16 N6 C2 In1 -166(100) 2 . . . ? C16 N6 C2 In1 14(100) . . . . ? N4 In1 C2 N4 180.0 . . . 2 ? N2 In1 C2 N4 96.85(10) . . . 2 ? N2 In1 C2 N4 -83.15(10) 2 . . 2 ? N1 In1 C2 N4 34.04(10) . . . 2 ? N1 In1 C2 N4 -145.96(10) 2 . . 2 ? C1 In1 C2 N4 68.65(10) . . . 2 ? C1 In1 C2 N4 -111.35(10) 2 . . 2 ? N4 In1 C2 N4 180.0 2 . . . ? N2 In1 C2 N4 -83.15(10) . . . . ? N2 In1 C2 N4 96.85(10) 2 . . . ? N1 In1 C2 N4 -145.96(10) . . . . ? N1 In1 C2 N4 34.04(10) 2 . . . ? C1 In1 C2 N4 -111.35(10) . . . . ? C1 In1 C2 N4 68.65(10) 2 . . . ? N4 In1 C2 N6 -145(100) 2 . . . ? N4 In1 C2 N6 35(100) . . . . ? N2 In1 C2 N6 -49(100) . . . . ? N2 In1 C2 N6 131(100) 2 . . . ? N1 In1 C2 N6 -111(100) . . . . ? N1 In1 C2 N6 69(100) 2 . . . ? C1 In1 C2 N6 -77(100) . . . . ? C1 In1 C2 N6 103(100) 2 . . . ? C2 N4 C13 C14 106.2(2) . . . . ? In1 N4 C13 C14 -39.1(3) . . . . ? C2 N4 C13 C15 -131.72(19) . . . . ? In1 N4 C13 C15 83.1(2) . . . . ? C2 N6 C16 C17 109.7(3) . . . . ? C16 N6 C16 C17 -70.3(3) 2 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.213 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 819611' ####################################################################### # # 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_cvd187s #TrackingRef '3_cvd187s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H60 In N9' _chemical_formula_weight 625.66 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' In In -0.7276 1.3100 '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)/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 16.2217(6) _cell_length_b 11.1470(3) _cell_length_c 23.0289(9) _cell_angle_alpha 90.00 _cell_angle_beta 109.239(3) _cell_angle_gamma 90.00 _cell_volume 3931.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 8570 _cell_measurement_theta_min 3.091 _cell_measurement_theta_max 36.684 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.057 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.626 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Sapphire2-CCD, Oxford Diffraction' _diffrn_measurement_method '586 images at 1.0 deg. in \w and 15 sec.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29196 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6896 _reflns_number_gt 6279 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD 1.171.13, Oxford Diffraction' _computing_cell_refinement 'CrysAlis RED 1.171.13, Oxford Diffraction' _computing_data_reduction 'CrysAlis RED 1.171.13, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXS-97 (Sheldrick, 1990)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0286P)^2^+12.3891P] 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 6896 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1037 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.202 _refine_ls_restrained_S_all 1.202 _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 In1 In 0.298930(15) 0.79176(2) 0.074315(10) 0.01516(9) Uani 1 1 d . . . N1 N 0.30195(19) 0.9874(2) 0.10071(13) 0.0183(6) Uani 1 1 d . . . N2 N 0.39024(18) 0.8568(3) 0.16657(12) 0.0163(6) Uani 1 1 d . . . N3 N 0.3956(2) 1.0619(3) 0.19808(14) 0.0270(7) Uani 1 1 d . . . N6 N 0.3509(2) 0.7750(3) -0.08680(14) 0.0269(7) Uani 1 1 d . . . N5 N 0.25442(18) 0.8034(3) -0.02914(12) 0.0176(6) Uani 1 1 d . . . N4 N 0.39476(18) 0.7652(3) 0.02328(12) 0.0172(6) Uani 1 1 d . . . N7 N 0.17470(18) 0.7344(3) 0.09087(13) 0.0182(6) Uani 1 1 d . . . N9 N 0.1542(2) 0.5343(3) 0.12149(15) 0.0274(7) Uani 1 1 d . . . N8 N 0.28199(19) 0.6003(3) 0.10051(13) 0.0185(6) Uani 1 1 d . . . C1 C 0.3630(2) 0.9695(3) 0.15529(15) 0.0172(7) Uani 1 1 d . . . C2 C 0.2872(2) 1.1047(3) 0.06956(16) 0.0210(7) Uani 1 1 d . . . H2A H 0.3242 1.1658 0.0983 0.025 Uiso 1 1 calc R . . C3 C 0.1921(3) 1.1414(4) 0.0534(2) 0.0338(9) Uani 1 1 d . . . H3A H 0.1760 1.1430 0.0909 0.051 Uiso 1 1 calc R . . H3B H 0.1551 1.0836 0.0243 0.051 Uiso 1 1 calc R . . H3C H 0.1839 1.2214 0.0347 0.051 Uiso 1 1 calc R . . C4 C 0.3137(3) 1.1004(4) 0.01194(19) 0.0322(9) Uani 1 1 d . . . H4A H 0.3753 1.0772 0.0232 0.048 Uiso 1 1 calc R . . H4B H 0.3054 1.1798 -0.0075 0.048 Uiso 1 1 calc R . . H4C H 0.2775 1.0416 -0.0169 0.048 Uiso 1 1 calc R . . C5 C 0.3392(3) 1.1514(3) 0.21085(18) 0.0321(9) Uani 1 1 d . . . H5A H 0.2781 1.1299 0.1896 0.048 Uiso 1 1 calc R . . H5B H 0.3514 1.2299 0.1963 0.048 Uiso 1 1 calc R . . H5C H 0.3499 1.1550 0.2553 0.048 Uiso 1 1 calc R . . C6 C 0.4883(3) 1.0805(4) 0.2261(2) 0.0373(10) Uani 1 1 d . . . H6A H 0.5199 1.0146 0.2147 0.056 Uiso 1 1 calc R . . H6B H 0.5031 1.0828 0.2709 0.056 Uiso 1 1 calc R . . H6C H 0.5047 1.1566 0.2117 0.056 Uiso 1 1 calc R . . C7 C 0.4334(2) 0.8107(3) 0.22901(15) 0.0190(7) Uani 1 1 d . . . H7A H 0.4436 0.8790 0.2587 0.023 Uiso 1 1 calc R . . C8 C 0.3771(3) 0.7176(3) 0.24614(17) 0.0272(8) Uani 1 1 d . . . H8A H 0.3207 0.7534 0.2434 0.041 Uiso 1 1 calc R . . H8B H 0.4066 0.6898 0.2883 0.041 Uiso 1 1 calc R . . H8C H 0.3675 0.6495 0.2178 0.041 Uiso 1 1 calc R . . C9 C 0.5218(3) 0.7553(4) 0.23334(18) 0.0315(9) Uani 1 1 d . . . H9A H 0.5580 0.8158 0.2224 0.047 Uiso 1 1 calc R . . H9B H 0.5126 0.6873 0.2050 0.047 Uiso 1 1 calc R . . H9C H 0.5514 0.7275 0.2755 0.047 Uiso 1 1 calc R . . C10 C 0.3339(2) 0.7813(3) -0.03154(15) 0.0172(7) Uani 1 1 d . . . C11 C 0.4884(2) 0.7840(3) 0.03413(15) 0.0197(7) Uani 1 1 d . . . H11A H 0.4968 0.7984 -0.0064 0.024 Uiso 1 1 calc R . . C12 C 0.5224(2) 0.8923(4) 0.07481(17) 0.0253(8) Uani 1 1 d . . . H12A H 0.4891 0.9636 0.0557 0.038 Uiso 1 1 calc R . . H12B H 0.5843 0.9044 0.0799 0.038 Uiso 1 1 calc R . . H12C H 0.5159 0.8790 0.1151 0.038 Uiso 1 1 calc R . . C13 C 0.5399(3) 0.6719(4) 0.06301(19) 0.0300(9) Uani 1 1 d . . . H13A H 0.5174 0.6027 0.0362 0.045 Uiso 1 1 calc R . . H13B H 0.5334 0.6575 0.1033 0.045 Uiso 1 1 calc R . . H13C H 0.6017 0.6837 0.0681 0.045 Uiso 1 1 calc R . . C14 C 0.4102(3) 0.6872(5) -0.0972(2) 0.0495(13) Uani 1 1 d . . . H14A H 0.4284 0.6313 -0.0624 0.074 Uiso 1 1 calc R . . H14B H 0.4617 0.7280 -0.1010 0.074 Uiso 1 1 calc R . . H14C H 0.3808 0.6428 -0.1351 0.074 Uiso 1 1 calc R . . C15 C 0.3179(3) 0.8643(4) -0.13458(17) 0.0323(9) Uani 1 1 d . . . H15A H 0.2787 0.9192 -0.1230 0.048 Uiso 1 1 calc R . . H15B H 0.2858 0.8244 -0.1734 0.048 Uiso 1 1 calc R . . H15C H 0.3668 0.9096 -0.1397 0.048 Uiso 1 1 calc R . . C16 C 0.1738(2) 0.7822(3) -0.08102(16) 0.0233(8) Uani 1 1 d . . . H16A H 0.1883 0.7837 -0.1200 0.028 Uiso 1 1 calc R . . C17 C 0.1099(3) 0.8818(5) -0.0834(2) 0.0556(15) Uani 1 1 d . . . H17A H 0.1369 0.9592 -0.0864 0.083 Uiso 1 1 calc R . . H17B H 0.0938 0.8801 -0.0460 0.083 Uiso 1 1 calc R . . H17C H 0.0575 0.8708 -0.1194 0.083 Uiso 1 1 calc R . . C18 C 0.1348(4) 0.6622(5) -0.0757(3) 0.071(2) Uani 1 1 d . . . H18A H 0.1775 0.5989 -0.0740 0.106 Uiso 1 1 calc R . . H18B H 0.0825 0.6493 -0.1116 0.106 Uiso 1 1 calc R . . H18C H 0.1189 0.6600 -0.0382 0.106 Uiso 1 1 calc R . . C19 C 0.2031(2) 0.6211(3) 0.10443(15) 0.0191(7) Uani 1 1 d . . . C20 C 0.1083(2) 0.7867(3) 0.11412(16) 0.0205(7) Uani 1 1 d . . . H20A H 0.0839 0.7214 0.1334 0.025 Uiso 1 1 calc R . . C21 C 0.1482(3) 0.8824(4) 0.16255(18) 0.0286(8) Uani 1 1 d . . . H21A H 0.1964 0.8474 0.1961 0.043 Uiso 1 1 calc R . . H21B H 0.1036 0.9129 0.1789 0.043 Uiso 1 1 calc R . . H21C H 0.1704 0.9485 0.1438 0.043 Uiso 1 1 calc R . . C22 C 0.0341(3) 0.8409(4) 0.0614(2) 0.0385(10) Uani 1 1 d . . . H22A H 0.0093 0.7794 0.0301 0.058 Uiso 1 1 calc R . . H22B H 0.0566 0.9073 0.0431 0.058 Uiso 1 1 calc R . . H22C H -0.0113 0.8709 0.0771 0.058 Uiso 1 1 calc R . . C23 C 0.0633(3) 0.5150(4) 0.0878(2) 0.0410(11) Uani 1 1 d . . . H23A H 0.0430 0.5762 0.0557 0.061 Uiso 1 1 calc R . . H23B H 0.0294 0.5204 0.1160 0.061 Uiso 1 1 calc R . . H23C H 0.0556 0.4352 0.0689 0.061 Uiso 1 1 calc R . . C24 C 0.1941(3) 0.4506(4) 0.17130(19) 0.0322(9) Uani 1 1 d . . . H24A H 0.2556 0.4720 0.1912 0.048 Uiso 1 1 calc R . . H24B H 0.1902 0.3691 0.1547 0.048 Uiso 1 1 calc R . . H24C H 0.1634 0.4545 0.2015 0.048 Uiso 1 1 calc R . . C25 C 0.3114(2) 0.4796(3) 0.09077(16) 0.0213(7) Uani 1 1 d . . . H25A H 0.2679 0.4200 0.0953 0.026 Uiso 1 1 calc R . . C26 C 0.3172(3) 0.4675(4) 0.02645(19) 0.0364(10) Uani 1 1 d . . . H26A H 0.2602 0.4853 -0.0041 0.055 Uiso 1 1 calc R . . H26B H 0.3345 0.3854 0.0204 0.055 Uiso 1 1 calc R . . H26C H 0.3608 0.5239 0.0215 0.055 Uiso 1 1 calc R . . C27 C 0.3991(3) 0.4525(4) 0.1388(2) 0.0316(9) Uani 1 1 d . . . H27A H 0.3943 0.4603 0.1800 0.047 Uiso 1 1 calc R . . H27B H 0.4428 0.5093 0.1345 0.047 Uiso 1 1 calc R . . H27C H 0.4169 0.3706 0.1331 0.047 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 In1 0.01849(13) 0.01456(13) 0.01318(13) 0.00041(9) 0.00625(9) -0.00078(9) N1 0.0216(15) 0.0132(14) 0.0224(15) 0.0030(12) 0.0105(12) 0.0021(11) N2 0.0207(14) 0.0183(15) 0.0100(13) -0.0009(11) 0.0050(11) 0.0002(12) N3 0.0319(17) 0.0211(16) 0.0234(16) -0.0106(13) 0.0031(14) 0.0013(13) N6 0.0292(17) 0.0373(19) 0.0160(15) 0.0011(13) 0.0097(13) 0.0040(14) N5 0.0189(14) 0.0211(15) 0.0132(13) 0.0003(11) 0.0061(11) -0.0022(12) N4 0.0196(14) 0.0206(15) 0.0124(13) -0.0009(11) 0.0066(11) -0.0015(12) N7 0.0203(15) 0.0186(15) 0.0165(14) 0.0023(12) 0.0069(12) -0.0002(12) N9 0.0282(17) 0.0255(17) 0.0303(17) 0.0076(14) 0.0120(14) -0.0035(14) N8 0.0253(16) 0.0158(15) 0.0140(14) 0.0018(11) 0.0059(12) 0.0012(12) C1 0.0200(17) 0.0187(17) 0.0157(16) -0.0026(13) 0.0096(14) -0.0014(14) C2 0.0272(19) 0.0138(17) 0.0189(17) 0.0033(14) 0.0036(15) 0.0004(14) C3 0.039(2) 0.027(2) 0.035(2) 0.0088(17) 0.0112(19) 0.0099(18) C4 0.048(2) 0.024(2) 0.030(2) 0.0093(17) 0.0191(19) 0.0016(18) C5 0.053(3) 0.021(2) 0.026(2) -0.0052(16) 0.0175(19) 0.0051(18) C6 0.042(2) 0.032(2) 0.032(2) -0.0077(18) 0.0052(19) -0.0130(19) C7 0.0232(17) 0.0238(18) 0.0093(15) -0.0011(13) 0.0043(13) 0.0045(14) C8 0.036(2) 0.026(2) 0.0192(18) 0.0039(15) 0.0083(16) 0.0035(17) C9 0.030(2) 0.043(2) 0.0198(19) 0.0046(17) 0.0056(16) 0.0123(18) C10 0.0235(17) 0.0146(16) 0.0132(16) -0.0012(13) 0.0060(13) -0.0044(13) C11 0.0188(17) 0.0279(19) 0.0144(16) -0.0014(14) 0.0084(13) -0.0014(15) C12 0.0215(18) 0.031(2) 0.0242(19) -0.0008(16) 0.0081(15) -0.0046(16) C13 0.025(2) 0.035(2) 0.029(2) -0.0031(17) 0.0082(16) 0.0036(17) C14 0.055(3) 0.068(3) 0.023(2) -0.014(2) 0.009(2) 0.022(3) C15 0.044(2) 0.038(2) 0.0160(18) 0.0035(16) 0.0109(17) -0.0073(19) C16 0.0225(18) 0.030(2) 0.0148(17) 0.0015(15) 0.0034(14) -0.0059(15) C17 0.038(3) 0.077(4) 0.034(3) -0.013(3) -0.013(2) 0.019(3) C18 0.056(3) 0.055(3) 0.069(4) 0.018(3) -0.024(3) -0.032(3) C19 0.0222(17) 0.0220(18) 0.0135(16) 0.0002(14) 0.0066(13) -0.0044(14) C20 0.0190(17) 0.0244(19) 0.0197(17) 0.0037(14) 0.0086(14) 0.0040(15) C21 0.030(2) 0.027(2) 0.034(2) 0.0001(17) 0.0179(17) 0.0027(17) C22 0.028(2) 0.053(3) 0.034(2) 0.010(2) 0.0097(18) 0.016(2) C23 0.035(2) 0.038(2) 0.052(3) -0.003(2) 0.016(2) -0.014(2) C24 0.049(2) 0.022(2) 0.036(2) 0.0097(17) 0.028(2) 0.0002(18) C25 0.032(2) 0.0175(18) 0.0177(17) -0.0010(14) 0.0118(15) -0.0018(15) C26 0.065(3) 0.022(2) 0.029(2) -0.0033(17) 0.024(2) 0.003(2) C27 0.033(2) 0.022(2) 0.043(2) 0.0030(17) 0.0173(19) 0.0070(17) _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 In1 N5 2.254(3) . ? In1 N4 2.256(3) . ? In1 N8 2.259(3) . ? In1 N1 2.261(3) . ? In1 N7 2.263(3) . ? In1 N2 2.271(3) . ? In1 C10 2.681(3) . ? In1 C1 2.684(3) . ? In1 C19 2.688(3) . ? N1 C1 1.334(4) . ? N1 C2 1.472(4) . ? N2 C1 1.329(4) . ? N2 C7 1.469(4) . ? N3 C1 1.403(4) . ? N3 C6 1.442(5) . ? N3 C5 1.448(5) . ? N6 C10 1.390(4) . ? N6 C14 1.447(5) . ? N6 C15 1.449(5) . ? N5 C10 1.332(4) . ? N5 C16 1.470(4) . ? N4 C10 1.334(4) . ? N4 C11 1.472(4) . ? N7 C19 1.346(5) . ? N7 C20 1.472(4) . ? N9 C19 1.387(5) . ? N9 C23 1.438(5) . ? N9 C24 1.454(5) . ? N8 C19 1.332(5) . ? N8 C25 1.470(4) . ? C2 C3 1.519(5) . ? C2 C4 1.524(5) . ? C2 H2A 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.518(5) . ? C7 C9 1.534(5) . ? C7 H7A 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C11 C12 1.516(5) . ? C11 C13 1.527(5) . ? C11 H11A 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C18 1.503(6) . ? C16 C17 1.507(6) . ? C16 H16A 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C20 C22 1.525(5) . ? C20 C21 1.525(5) . ? C20 H20A 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C27 1.517(5) . ? C25 C26 1.521(5) . ? C25 H25A 1.0000 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? 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 N5 In1 N4 59.51(10) . . ? N5 In1 N8 108.17(10) . . ? N4 In1 N8 100.41(10) . . ? N5 In1 N1 101.52(10) . . ? N4 In1 N1 108.00(10) . . ? N8 In1 N1 146.46(10) . . ? N5 In1 N7 101.62(10) . . ? N4 In1 N7 148.81(10) . . ? N8 In1 N7 59.65(10) . . ? N1 In1 N7 99.72(10) . . ? N5 In1 N2 148.58(10) . . ? N4 In1 N2 100.38(10) . . ? N8 In1 N2 98.67(10) . . ? N1 In1 N2 59.40(10) . . ? N7 In1 N2 105.96(10) . . ? N5 In1 C10 29.72(10) . . ? N4 In1 C10 29.78(10) . . ? N8 In1 C10 106.41(10) . . ? N1 In1 C10 107.10(10) . . ? N7 In1 C10 127.44(10) . . ? N2 In1 C10 126.60(10) . . ? N5 In1 C1 127.42(10) . . ? N4 In1 C1 106.47(10) . . ? N8 In1 C1 124.41(10) . . ? N1 In1 C1 29.75(10) . . ? N7 In1 C1 104.69(10) . . ? N2 In1 C1 29.65(10) . . ? C10 In1 C1 120.95(10) . . ? N5 In1 C19 107.60(10) . . ? N4 In1 C19 126.72(11) . . ? N8 In1 C19 29.65(11) . . ? N1 In1 C19 125.21(10) . . ? N7 In1 C19 30.00(11) . . ? N2 In1 C19 103.81(10) . . ? C10 In1 C19 121.16(10) . . ? C1 In1 C19 117.86(10) . . ? C1 N1 C2 122.9(3) . . ? C1 N1 In1 93.0(2) . . ? C2 N1 In1 137.7(2) . . ? C1 N2 C7 122.9(3) . . ? C1 N2 In1 92.6(2) . . ? C7 N2 In1 139.2(2) . . ? C1 N3 C6 121.1(3) . . ? C1 N3 C5 122.1(3) . . ? C6 N3 C5 116.5(3) . . ? C10 N6 C14 121.9(3) . . ? C10 N6 C15 121.7(3) . . ? C14 N6 C15 116.0(3) . . ? C10 N5 C16 123.4(3) . . ? C10 N5 In1 93.2(2) . . ? C16 N5 In1 137.6(2) . . ? C10 N4 C11 122.8(3) . . ? C10 N4 In1 93.1(2) . . ? C11 N4 In1 138.0(2) . . ? C19 N7 C20 121.5(3) . . ? C19 N7 In1 92.8(2) . . ? C20 N7 In1 138.5(2) . . ? C19 N9 C23 122.1(3) . . ? C19 N9 C24 121.6(3) . . ? C23 N9 C24 116.1(3) . . ? C19 N8 C25 122.5(3) . . ? C19 N8 In1 93.3(2) . . ? C25 N8 In1 138.6(2) . . ? N2 C1 N1 114.9(3) . . ? N2 C1 N3 122.2(3) . . ? N1 C1 N3 122.9(3) . . ? N2 C1 In1 57.70(17) . . ? N1 C1 In1 57.25(17) . . ? N3 C1 In1 179.2(3) . . ? N1 C2 C3 110.3(3) . . ? N1 C2 C4 110.5(3) . . ? C3 C2 C4 110.5(3) . . ? N1 C2 H2A 108.5 . . ? C3 C2 H2A 108.5 . . ? C4 C2 H2A 108.5 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 H5A 109.5 . . ? N3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 C8 111.1(3) . . ? N2 C7 C9 109.8(3) . . ? C8 C7 C9 109.8(3) . . ? N2 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? C9 C7 H7A 108.7 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N5 C10 N4 114.2(3) . . ? N5 C10 N6 122.3(3) . . ? N4 C10 N6 123.5(3) . . ? N5 C10 In1 57.07(17) . . ? N4 C10 In1 57.15(17) . . ? N6 C10 In1 179.2(3) . . ? N4 C11 C12 111.3(3) . . ? N4 C11 C13 110.0(3) . . ? C12 C11 C13 110.3(3) . . ? N4 C11 H11A 108.4 . . ? C12 C11 H11A 108.4 . . ? C13 C11 H11A 108.4 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N6 C14 H14A 109.5 . . ? N6 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N6 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N6 C15 H15A 109.5 . . ? N6 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N6 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N5 C16 C18 111.3(3) . . ? N5 C16 C17 109.2(3) . . ? C18 C16 C17 110.8(4) . . ? N5 C16 H16A 108.5 . . ? C18 C16 H16A 108.5 . . ? C17 C16 H16A 108.5 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N8 C19 N7 114.3(3) . . ? N8 C19 N9 123.3(3) . . ? N7 C19 N9 122.4(3) . . ? N8 C19 In1 57.03(17) . . ? N7 C19 In1 57.23(17) . . ? N9 C19 In1 178.5(3) . . ? N7 C20 C22 110.4(3) . . ? N7 C20 C21 110.9(3) . . ? C22 C20 C21 109.8(3) . . ? N7 C20 H20A 108.6 . . ? C22 C20 H20A 108.6 . . ? C21 C20 H20A 108.6 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N9 C23 H23A 109.5 . . ? N9 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N9 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N9 C24 H24A 109.5 . . ? N9 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N9 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N8 C25 C27 110.1(3) . . ? N8 C25 C26 110.9(3) . . ? C27 C25 C26 110.4(3) . . ? N8 C25 H25A 108.4 . . ? C27 C25 H25A 108.4 . . ? C26 C25 H25A 108.4 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? 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 N5 In1 N1 C1 -153.27(19) . . . . ? N4 In1 N1 C1 -91.8(2) . . . . ? N8 In1 N1 C1 54.7(3) . . . . ? N7 In1 N1 C1 102.6(2) . . . . ? N2 In1 N1 C1 -0.23(18) . . . . ? C10 In1 N1 C1 -123.1(2) . . . . ? C19 In1 N1 C1 85.3(2) . . . . ? N5 In1 N1 C2 -3.2(3) . . . . ? N4 In1 N1 C2 58.2(3) . . . . ? N8 In1 N1 C2 -155.3(3) . . . . ? N7 In1 N1 C2 -107.3(3) . . . . ? N2 In1 N1 C2 149.8(4) . . . . ? C10 In1 N1 C2 26.9(4) . . . . ? C1 In1 N1 C2 150.0(4) . . . . ? C19 In1 N1 C2 -124.7(3) . . . . ? N5 In1 N2 C1 58.7(3) . . . . ? N4 In1 N2 C1 105.1(2) . . . . ? N8 In1 N2 C1 -152.6(2) . . . . ? N1 In1 N2 C1 0.23(18) . . . . ? N7 In1 N2 C1 -91.8(2) . . . . ? C10 In1 N2 C1 89.5(2) . . . . ? C19 In1 N2 C1 -122.8(2) . . . . ? N5 In1 N2 C7 -149.0(3) . . . . ? N4 In1 N2 C7 -102.6(3) . . . . ? N8 In1 N2 C7 -0.2(3) . . . . ? N1 In1 N2 C7 152.6(4) . . . . ? N7 In1 N2 C7 60.6(3) . . . . ? C10 In1 N2 C7 -118.2(3) . . . . ? C1 In1 N2 C7 152.3(4) . . . . ? C19 In1 N2 C7 29.6(3) . . . . ? N4 In1 N5 C10 0.14(19) . . . . ? N8 In1 N5 C10 -91.4(2) . . . . ? N1 In1 N5 C10 104.4(2) . . . . ? N7 In1 N5 C10 -153.0(2) . . . . ? N2 In1 N5 C10 55.9(3) . . . . ? C1 In1 N5 C10 88.0(2) . . . . ? C19 In1 N5 C10 -122.6(2) . . . . ? N4 In1 N5 C16 151.7(4) . . . . ? N8 In1 N5 C16 60.1(4) . . . . ? N1 In1 N5 C16 -104.0(3) . . . . ? N7 In1 N5 C16 -1.5(4) . . . . ? N2 In1 N5 C16 -152.5(3) . . . . ? C10 In1 N5 C16 151.6(5) . . . . ? C1 In1 N5 C16 -120.4(3) . . . . ? C19 In1 N5 C16 29.0(4) . . . . ? N5 In1 N4 C10 -0.14(19) . . . . ? N8 In1 N4 C10 104.9(2) . . . . ? N1 In1 N4 C10 -93.1(2) . . . . ? N7 In1 N4 C10 58.4(3) . . . . ? N2 In1 N4 C10 -154.2(2) . . . . ? C1 In1 N4 C10 -124.3(2) . . . . ? C19 In1 N4 C10 89.8(2) . . . . ? N5 In1 N4 C11 150.5(4) . . . . ? N8 In1 N4 C11 -104.5(3) . . . . ? N1 In1 N4 C11 57.5(3) . . . . ? N7 In1 N4 C11 -151.0(3) . . . . ? N2 In1 N4 C11 -3.5(3) . . . . ? C10 In1 N4 C11 150.6(4) . . . . ? C1 In1 N4 C11 26.3(4) . . . . ? C19 In1 N4 C11 -119.6(3) . . . . ? N5 In1 N7 C19 105.1(2) . . . . ? N4 In1 N7 C19 56.5(3) . . . . ? N8 In1 N7 C19 0.75(18) . . . . ? N1 In1 N7 C19 -150.9(2) . . . . ? N2 In1 N7 C19 -90.1(2) . . . . ? C10 In1 N7 C19 88.7(2) . . . . ? C1 In1 N7 C19 -120.8(2) . . . . ? N5 In1 N7 C20 -107.3(3) . . . . ? N4 In1 N7 C20 -155.9(3) . . . . ? N8 In1 N7 C20 148.3(4) . . . . ? N1 In1 N7 C20 -3.3(3) . . . . ? N2 In1 N7 C20 57.5(3) . . . . ? C10 In1 N7 C20 -123.7(3) . . . . ? C1 In1 N7 C20 26.8(3) . . . . ? C19 In1 N7 C20 147.6(4) . . . . ? N5 In1 N8 C19 -93.8(2) . . . . ? N4 In1 N8 C19 -154.96(19) . . . . ? N1 In1 N8 C19 57.3(3) . . . . ? N7 In1 N8 C19 -0.76(18) . . . . ? N2 In1 N8 C19 102.7(2) . . . . ? C10 In1 N8 C19 -124.9(2) . . . . ? C1 In1 N8 C19 86.7(2) . . . . ? N5 In1 N8 C25 57.7(4) . . . . ? N4 In1 N8 C25 -3.4(3) . . . . ? N1 In1 N8 C25 -151.2(3) . . . . ? N7 In1 N8 C25 150.8(4) . . . . ? N2 In1 N8 C25 -105.7(3) . . . . ? C10 In1 N8 C25 26.6(4) . . . . ? C1 In1 N8 C25 -121.8(3) . . . . ? C19 In1 N8 C25 151.5(4) . . . . ? C7 N2 C1 N1 -159.2(3) . . . . ? In1 N2 C1 N1 -0.4(3) . . . . ? C7 N2 C1 N3 20.2(5) . . . . ? In1 N2 C1 N3 179.0(3) . . . . ? C7 N2 C1 In1 -158.8(3) . . . . ? C2 N1 C1 N2 -156.0(3) . . . . ? In1 N1 C1 N2 0.4(3) . . . . ? C2 N1 C1 N3 24.6(5) . . . . ? In1 N1 C1 N3 -179.0(3) . . . . ? C2 N1 C1 In1 -156.4(3) . . . . ? C6 N3 C1 N2 50.9(5) . . . . ? C5 N3 C1 N2 -136.6(4) . . . . ? C6 N3 C1 N1 -129.8(4) . . . . ? C5 N3 C1 N1 42.8(5) . . . . ? C6 N3 C1 In1 132(21) . . . . ? C5 N3 C1 In1 -56(21) . . . . ? N5 In1 C1 N2 -145.89(19) . . . . ? N4 In1 C1 N2 -82.0(2) . . . . ? N8 In1 C1 N2 33.5(2) . . . . ? N1 In1 C1 N2 -179.6(3) . . . . ? N7 In1 C1 N2 96.5(2) . . . . ? C10 In1 C1 N2 -110.6(2) . . . . ? C19 In1 C1 N2 67.5(2) . . . . ? N5 In1 C1 N1 33.7(2) . . . . ? N4 In1 C1 N1 97.6(2) . . . . ? N8 In1 C1 N1 -146.89(19) . . . . ? N7 In1 C1 N1 -83.9(2) . . . . ? N2 In1 C1 N1 179.6(3) . . . . ? C10 In1 C1 N1 69.0(2) . . . . ? C19 In1 C1 N1 -112.9(2) . . . . ? N5 In1 C1 N3 133(21) . . . . ? N4 In1 C1 N3 -163(21) . . . . ? N8 In1 C1 N3 -48(21) . . . . ? N1 In1 C1 N3 99(21) . . . . ? N7 In1 C1 N3 15(21) . . . . ? N2 In1 C1 N3 -81(21) . . . . ? C10 In1 C1 N3 168(21) . . . . ? C19 In1 C1 N3 -14(21) . . . . ? C1 N1 C2 C3 -125.8(4) . . . . ? In1 N1 C2 C3 90.7(4) . . . . ? C1 N1 C2 C4 111.7(4) . . . . ? In1 N1 C2 C4 -31.8(5) . . . . ? C1 N2 C7 C8 113.4(4) . . . . ? In1 N2 C7 C8 -33.1(5) . . . . ? C1 N2 C7 C9 -125.0(4) . . . . ? In1 N2 C7 C9 88.5(4) . . . . ? C16 N5 C10 N4 -157.6(3) . . . . ? In1 N5 C10 N4 -0.2(3) . . . . ? C16 N5 C10 N6 22.0(5) . . . . ? In1 N5 C10 N6 179.4(3) . . . . ? C16 N5 C10 In1 -157.4(4) . . . . ? C11 N4 C10 N5 -156.8(3) . . . . ? In1 N4 C10 N5 0.2(3) . . . . ? C11 N4 C10 N6 23.6(5) . . . . ? In1 N4 C10 N6 -179.4(3) . . . . ? C11 N4 C10 In1 -157.0(3) . . . . ? C14 N6 C10 N5 -140.7(4) . . . . ? C15 N6 C10 N5 46.3(5) . . . . ? C14 N6 C10 N4 38.9(6) . . . . ? C15 N6 C10 N4 -134.2(4) . . . . ? C14 N6 C10 In1 -102(20) . . . . ? C15 N6 C10 In1 85(20) . . . . ? N4 In1 C10 N5 -179.8(3) . . . . ? N8 In1 C10 N5 98.0(2) . . . . ? N1 In1 C10 N5 -83.3(2) . . . . ? N7 In1 C10 N5 34.0(2) . . . . ? N2 In1 C10 N5 -147.48(19) . . . . ? C1 In1 C10 N5 -112.3(2) . . . . ? C19 In1 C10 N5 69.7(2) . . . . ? N5 In1 C10 N4 179.8(3) . . . . ? N8 In1 C10 N4 -82.2(2) . . . . ? N1 In1 C10 N4 96.5(2) . . . . ? N7 In1 C10 N4 -146.24(19) . . . . ? N2 In1 C10 N4 32.3(2) . . . . ? C1 In1 C10 N4 67.5(2) . . . . ? C19 In1 C10 N4 -110.5(2) . . . . ? N5 In1 C10 N6 -39(20) . . . . ? N4 In1 C10 N6 141(20) . . . . ? N8 In1 C10 N6 59(20) . . . . ? N1 In1 C10 N6 -123(20) . . . . ? N7 In1 C10 N6 -5(20) . . . . ? N2 In1 C10 N6 173(100) . . . . ? C1 In1 C10 N6 -152(20) . . . . ? C19 In1 C10 N6 30(20) . . . . ? C10 N4 C11 C12 111.4(4) . . . . ? In1 N4 C11 C12 -32.9(5) . . . . ? C10 N4 C11 C13 -126.0(3) . . . . ? In1 N4 C11 C13 89.7(4) . . . . ? C10 N5 C16 C18 95.8(5) . . . . ? In1 N5 C16 C18 -49.5(5) . . . . ? C10 N5 C16 C17 -141.6(4) . . . . ? In1 N5 C16 C17 73.1(5) . . . . ? C25 N8 C19 N7 -156.9(3) . . . . ? In1 N8 C19 N7 1.2(3) . . . . ? C25 N8 C19 N9 23.7(5) . . . . ? In1 N8 C19 N9 -178.3(3) . . . . ? C25 N8 C19 In1 -158.1(3) . . . . ? C20 N7 C19 N8 -156.6(3) . . . . ? In1 N7 C19 N8 -1.2(3) . . . . ? C20 N7 C19 N9 22.9(5) . . . . ? In1 N7 C19 N9 178.3(3) . . . . ? C20 N7 C19 In1 -155.4(3) . . . . ? C23 N9 C19 N8 -132.9(4) . . . . ? C24 N9 C19 N8 41.5(5) . . . . ? C23 N9 C19 N7 47.6(5) . . . . ? C24 N9 C19 N7 -137.9(4) . . . . ? C23 N9 C19 In1 124(10) . . . . ? C24 N9 C19 In1 -62(10) . . . . ? N5 In1 C19 N8 96.0(2) . . . . ? N4 In1 C19 N8 31.3(2) . . . . ? N1 In1 C19 N8 -145.32(19) . . . . ? N7 In1 C19 N8 178.7(3) . . . . ? N2 In1 C19 N8 -83.2(2) . . . . ? C10 In1 C19 N8 66.8(2) . . . . ? C1 In1 C19 N8 -111.3(2) . . . . ? N5 In1 C19 N7 -82.7(2) . . . . ? N4 In1 C19 N7 -147.41(19) . . . . ? N8 In1 C19 N7 -178.7(3) . . . . ? N1 In1 C19 N7 36.0(2) . . . . ? N2 In1 C19 N7 98.1(2) . . . . ? C10 In1 C19 N7 -111.9(2) . . . . ? C1 In1 C19 N7 70.0(2) . . . . ? N5 In1 C19 N9 -160(10) . . . . ? N4 In1 C19 N9 136(10) . . . . ? N8 In1 C19 N9 104(10) . . . . ? N1 In1 C19 N9 -41(10) . . . . ? N7 In1 C19 N9 -77(10) . . . . ? N2 In1 C19 N9 21(10) . . . . ? C10 In1 C19 N9 171(10) . . . . ? C1 In1 C19 N9 -7(10) . . . . ? C19 N7 C20 C22 -128.3(4) . . . . ? In1 N7 C20 C22 90.6(4) . . . . ? C19 N7 C20 C21 109.8(4) . . . . ? In1 N7 C20 C21 -31.3(5) . . . . ? C19 N8 C25 C27 -128.3(3) . . . . ? In1 N8 C25 C27 86.0(4) . . . . ? C19 N8 C25 C26 109.2(4) . . . . ? In1 N8 C25 C26 -36.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.908 _refine_diff_density_min -0.567 _refine_diff_density_rms 0.088 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.250 0.038 0.750 414 68 ' ' 2 0.750 0.027 0.250 414 68 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 831071'