# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Anne Richards' _publ_contact_author_email a.richards@latrobe.edu.au _publ_author_name 'Anne Richards' data_ar118 _database_code_depnum_ccdc_archive 'CCDC 861498' #TrackingRef '- 1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (NO-NO-AlMe3)2 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H30 Al2 N2 O2' _chemical_formula_weight 336.38 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' Al Al 0.0645 0.0514 '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 5.8360(6) _cell_length_b 8.5491(10) _cell_length_c 10.8312(11) _cell_angle_alpha 68.177(10) _cell_angle_beta 80.886(8) _cell_angle_gamma 71.595(10) _cell_volume 475.49(9) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1297 _cell_measurement_theta_min 2.7398 _cell_measurement_theta_max 29.1366 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.175 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 182 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_T_min 0.99338 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Xcalibur, Atlas, Gemini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.3281 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3757 _diffrn_reflns_av_R_equivalents 0.0146 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 29.23 _reflns_number_total 2180 _reflns_number_gt 1926 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material SHELXL-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^)+(0.0510P)^2^+0.1719P] 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 2180 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 Al1 Al 0.32526(7) 0.36907(5) 0.79648(4) 0.02065(14) Uani 1 1 d . . . O1 O 0.0853(2) 0.49944(14) 0.68473(11) 0.0291(3) Uani 1 1 d . . . N1 N 0.3710(2) 0.56210(15) 0.83294(11) 0.0197(2) Uani 1 1 d . . . C1 C -0.0023(3) 0.66953(19) 0.64189(13) 0.0228(3) Uani 1 1 d . . . C2 C 0.0721(3) 0.77970(19) 0.68132(14) 0.0241(3) Uani 1 1 d . . . H2 H -0.0048 0.9018 0.6438 0.029 Uiso 1 1 calc R . . C3 C 0.2549(3) 0.72785(18) 0.77377(13) 0.0212(3) Uani 1 1 d . . . C4 C -0.1970(3) 0.7383(2) 0.54426(15) 0.0306(3) Uani 1 1 d . . . H4A H -0.1317 0.7058 0.4653 0.046 Uiso 1 1 calc R . . H4C H -0.2553 0.8665 0.5181 0.046 Uiso 1 1 calc R . . H4B H -0.3312 0.6877 0.5856 0.046 Uiso 1 1 calc R . . C5 C 0.3110(3) 0.87341(19) 0.79858(15) 0.0288(3) Uani 1 1 d . . . H5A H 0.4727 0.8810 0.7605 0.043 Uiso 1 1 calc R . . H5C H 0.3056 0.8492 0.8947 0.043 Uiso 1 1 calc R . . H5B H 0.1913 0.9849 0.7567 0.043 Uiso 1 1 calc R . . C6 C 0.5558(2) 0.51428(19) 0.92888(13) 0.0217(3) Uani 1 1 d . . . H6B H 0.6361 0.6088 0.9031 0.026 Uiso 1 1 calc R . . H6A H 0.6802 0.4054 0.9263 0.026 Uiso 1 1 calc R . . C7 C 0.6175(3) 0.2648(2) 0.70501(18) 0.0341(4) Uani 1 1 d . . . H7A H 0.5878 0.1761 0.6776 0.051 Uiso 1 1 calc R . . H7C H 0.7512 0.2096 0.7655 0.051 Uiso 1 1 calc R . . H7B H 0.6594 0.3566 0.6263 0.051 Uiso 1 1 calc R . . C8 C 0.1982(3) 0.2131(2) 0.95728(15) 0.0272(3) Uani 1 1 d . . . H8C H 0.1011 0.2812 1.0124 0.041 Uiso 1 1 calc R . . H8B H 0.3330 0.1215 1.0078 0.041 Uiso 1 1 calc R . . H8A H 0.0971 0.1586 0.9319 0.041 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 Al1 0.0217(2) 0.0203(2) 0.0222(2) -0.01003(17) -0.00217(16) -0.00500(17) O1 0.0334(6) 0.0260(5) 0.0316(6) -0.0111(4) -0.0124(4) -0.0067(5) N1 0.0209(6) 0.0214(6) 0.0181(5) -0.0080(4) -0.0032(4) -0.0051(5) C1 0.0218(7) 0.0278(7) 0.0171(6) -0.0070(5) -0.0010(5) -0.0053(6) C2 0.0268(7) 0.0214(7) 0.0202(7) -0.0051(5) -0.0045(5) -0.0025(6) C3 0.0244(7) 0.0219(7) 0.0183(6) -0.0084(5) 0.0011(5) -0.0071(6) C4 0.0273(8) 0.0387(9) 0.0242(7) -0.0088(6) -0.0076(6) -0.0065(7) C5 0.0390(9) 0.0213(7) 0.0285(8) -0.0085(6) -0.0062(6) -0.0094(7) C6 0.0206(7) 0.0244(7) 0.0210(7) -0.0093(5) -0.0046(5) -0.0041(6) C7 0.0313(8) 0.0358(9) 0.0413(9) -0.0230(7) 0.0060(7) -0.0096(7) C8 0.0284(8) 0.0252(7) 0.0288(8) -0.0088(6) -0.0004(6) -0.0096(6) _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 Al1 O1 1.7936(11) . ? Al1 N1 1.9358(12) . ? Al1 C7 1.9611(16) . ? Al1 C8 1.9620(15) . ? O1 C1 1.3020(18) . ? N1 C3 1.3168(18) . ? N1 C6 1.4733(17) . ? C1 C2 1.369(2) . ? C1 C4 1.5003(19) . ? C2 C3 1.4308(19) . ? C2 H2 0.9500 . ? C3 C5 1.5042(19) . ? C4 H4A 0.9800 . ? C4 H4C 0.9800 . ? C4 H4B 0.9800 . ? C5 H5A 0.9800 . ? C5 H5C 0.9800 . ? C5 H5B 0.9800 . ? C6 C6 1.536(3) 2_667 ? C6 H6B 0.9900 . ? C6 H6A 0.9900 . ? C7 H7A 0.9800 . ? C7 H7C 0.9800 . ? C7 H7B 0.9800 . ? C8 H8C 0.9800 . ? C8 H8B 0.9800 . ? C8 H8A 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 O1 Al1 N1 96.05(5) . . ? O1 Al1 C7 111.78(7) . . ? N1 Al1 C7 109.50(6) . . ? O1 Al1 C8 109.08(6) . . ? N1 Al1 C8 110.17(6) . . ? C7 Al1 C8 118.05(7) . . ? C1 O1 Al1 127.77(9) . . ? C3 N1 C6 120.44(12) . . ? C3 N1 Al1 123.74(10) . . ? C6 N1 Al1 115.77(9) . . ? O1 C1 C2 124.07(13) . . ? O1 C1 C4 114.39(13) . . ? C2 C1 C4 121.54(14) . . ? C1 C2 C3 125.99(13) . . ? C1 C2 H2 117.0 . . ? C3 C2 H2 117.0 . . ? N1 C3 C2 122.19(13) . . ? N1 C3 C5 121.40(13) . . ? C2 C3 C5 116.40(12) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? H4C C4 H4B 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? H5C C5 H5B 109.5 . . ? N1 C6 C6 111.41(14) . 2_667 ? N1 C6 H6B 109.3 . . ? C6 C6 H6B 109.3 2_667 . ? N1 C6 H6A 109.3 . . ? C6 C6 H6A 109.3 2_667 . ? H6B C6 H6A 108.0 . . ? Al1 C7 H7A 109.5 . . ? Al1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? Al1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? H7C C7 H7B 109.5 . . ? Al1 C8 H8C 109.5 . . ? Al1 C8 H8B 109.5 . . ? H8C C8 H8B 109.5 . . ? Al1 C8 H8A 109.5 . . ? H8C C8 H8A 109.5 . . ? H8B C8 H8A 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 N1 Al1 O1 C1 4.23(13) . . . . ? C7 Al1 O1 C1 -109.59(13) . . . . ? C8 Al1 O1 C1 118.03(13) . . . . ? O1 Al1 N1 C3 -4.60(12) . . . . ? C7 Al1 N1 C3 111.08(12) . . . . ? C8 Al1 N1 C3 -117.50(12) . . . . ? O1 Al1 N1 C6 178.06(9) . . . . ? C7 Al1 N1 C6 -66.25(11) . . . . ? C8 Al1 N1 C6 65.16(10) . . . . ? Al1 O1 C1 C2 -2.8(2) . . . . ? Al1 O1 C1 C4 177.59(10) . . . . ? O1 C1 C2 C3 0.2(2) . . . . ? C4 C1 C2 C3 179.79(13) . . . . ? C6 N1 C3 C2 -179.18(12) . . . . ? Al1 N1 C3 C2 3.60(19) . . . . ? C6 N1 C3 C5 1.8(2) . . . . ? Al1 N1 C3 C5 -175.40(10) . . . . ? C1 C2 C3 N1 -0.8(2) . . . . ? C1 C2 C3 C5 178.22(14) . . . . ? C3 N1 C6 C6 89.51(18) . . . 2_667 ? Al1 N1 C6 C6 -93.06(15) . . . 2_667 ? _diffrn_measured_fraction_theta_max 0.847 _diffrn_reflns_theta_full 26.25 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.305 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.045 # Attachment '- 2rev.CIF' data_ar300 _database_code_depnum_ccdc_archive 'CCDC 861499' #TrackingRef '- 2rev.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (((NO)AlCl(thf)2)I(thf)2) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H34 Al I N2 O4' _chemical_formula_weight 520.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Al Al 0.2130 0.2455 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2 / 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 12.7840(10) _cell_length_b 14.1352(9) _cell_length_c 29.117(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.139(7) _cell_angle_gamma 90.00 _cell_volume 5220.7(7) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4015 _cell_measurement_theta_min 3.0589 _cell_measurement_theta_max 74.0008 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.015 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2128 _exptl_absorpt_coefficient_mu 10.160 _exptl_absorpt_correction_T_min 0.16767 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9835 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 67.48 _reflns_number_total 4697 _reflns_number_gt 4041 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material SHELXL-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. 2 disordered molecules of thf was omitted from the final refinement cycles using SQUEEZE. Our attempts to model the disorder were unsuccessful. The relatively high wR2 values and residual electron density are associated with a the twinned nature of the crystal. Using the twinning feature of CrysalisPro, two cells were found, with the monoclinic cell being the major component. The refinement on both cells did not lead to a solution being found, therefore the data were processed normally. It can also be seen that the thermal parameters on some of the coordinated thf molecules are quite large, some atoms were split, others failed to give a stable refinement when using PART statement and were thus left. 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 0.000 0.950 0.250 272 53 ' ' 2 0.000 0.050 0.750 272 53 ' ' 3 0.500 0.450 0.250 272 53 ' ' 4 0.500 0.550 0.750 272 53 ' ' _platon_squeeze_details ; _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^)+(0.0933P)^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 4697 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1458 _refine_ls_wR_factor_gt 0.1395 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 Al1 Al 0.52273(8) 0.17964(8) 0.62900(3) 0.0233(2) Uani 1 1 d . . . N1 N 0.4073(2) 0.1013(2) 0.59933(10) 0.0271(7) Uani 1 1 d . . . N2 N 0.5940(2) 0.1441(2) 0.57578(10) 0.0261(7) Uani 1 1 d . . . O1 O 0.4514(2) 0.20407(19) 0.67791(9) 0.0278(6) Uani 1 1 d . . . O2 O 0.6318(2) 0.2531(2) 0.65320(9) 0.0274(6) Uani 1 1 d . . . O3 O 0.5896(2) 0.0648(2) 0.66307(9) 0.0303(6) Uani 1 1 d . . . O4 O 0.4561(2) 0.28994(19) 0.59361(10) 0.0304(6) Uani 1 1 d . C . I1 I 0.45587(2) 0.21995(2) 0.430865(10) 0.04620(16) Uani 1 1 d . . . C1 C 0.3602(3) 0.1741(3) 0.68754(13) 0.0275(8) Uani 1 1 d . . . C2 C 0.2960(3) 0.1150(3) 0.65905(14) 0.0320(9) Uani 1 1 d . . . H2 H 0.2330 0.0935 0.6698 0.038 Uiso 1 1 calc R . . C3 C 0.3170(3) 0.0837(3) 0.61457(13) 0.0300(8) Uani 1 1 d . . . C4 C 0.3295(4) 0.2089(3) 0.73228(15) 0.0345(9) Uani 1 1 d . . . H4A H 0.3839 0.1914 0.7576 0.052 Uiso 1 1 calc R . . H4B H 0.2622 0.1804 0.7376 0.052 Uiso 1 1 calc R . . H4C H 0.3222 0.2779 0.7311 0.052 Uiso 1 1 calc R . . C5 C 0.2306(3) 0.0312(4) 0.58551(16) 0.0424(11) Uani 1 1 d . . . H5A H 0.2106 0.0656 0.5565 0.064 Uiso 1 1 calc R . . H5B H 0.1692 0.0257 0.6025 0.064 Uiso 1 1 calc R . . H5C H 0.2555 -0.0322 0.5786 0.064 Uiso 1 1 calc R . . C6 C 0.4222(3) 0.0749(3) 0.55164(14) 0.0331(9) Uani 1 1 d . . . H6A H 0.3867 0.1218 0.5297 0.040 Uiso 1 1 calc R . . H6B H 0.3900 0.0122 0.5441 0.040 Uiso 1 1 calc R . . C7 C 0.5382(3) 0.0715(3) 0.54661(14) 0.0324(9) Uani 1 1 d . . . H7A H 0.5669 0.0083 0.5559 0.039 Uiso 1 1 calc R . . H7B H 0.5485 0.0823 0.5139 0.039 Uiso 1 1 calc R . . C8 C 0.7209(3) 0.2710(3) 0.63757(14) 0.0311(9) Uani 1 1 d . . . C9 C 0.7491(3) 0.2364(3) 0.59701(15) 0.0304(8) Uani 1 1 d . . . H9 H 0.8144 0.2569 0.5881 0.036 Uiso 1 1 calc R . . C10 C 0.6879(3) 0.1722(3) 0.56720(13) 0.0286(8) Uani 1 1 d . . . C11 C 0.7940(4) 0.3326(4) 0.66862(16) 0.0432(11) Uani 1 1 d . . . H11A H 0.7585 0.3922 0.6741 0.065 Uiso 1 1 calc R . . H11B H 0.8573 0.3457 0.6539 0.065 Uiso 1 1 calc R . . H11C H 0.8139 0.3002 0.6982 0.065 Uiso 1 1 calc R . . C12 C 0.7339(3) 0.1368(3) 0.52516(15) 0.0349(9) Uani 1 1 d . . . H12A H 0.7362 0.0675 0.5257 0.052 Uiso 1 1 calc R . . H12B H 0.8055 0.1617 0.5254 0.052 Uiso 1 1 calc R . . H12C H 0.6899 0.1581 0.4971 0.052 Uiso 1 1 calc R . . C13 C 0.7005(3) 0.0395(4) 0.66692(18) 0.0437(11) Uani 1 1 d . . . H13A H 0.7451 0.0934 0.6790 0.052 Uiso 1 1 calc R . . H13B H 0.7203 0.0211 0.6364 0.052 Uiso 1 1 calc R . . C15 C 0.6106(5) -0.0768(5) 0.7041(2) 0.0654(16) Uani 1 1 d . . . H15A H 0.6019 -0.0834 0.7372 0.078 Uiso 1 1 calc R . . H15B H 0.6008 -0.1398 0.6893 0.078 Uiso 1 1 calc R . . C16 C 0.5342(4) -0.0110(4) 0.6820(3) 0.0701(19) Uani 1 1 d . . . H16A H 0.4877 -0.0432 0.6571 0.084 Uiso 1 1 calc R . . H16B H 0.4900 0.0140 0.7048 0.084 Uiso 1 1 calc R . . C17 C 0.5066(4) 0.3514(4) 0.56297(18) 0.0458(11) Uani 1 1 d . C . H17A H 0.5320 0.3140 0.5378 0.055 Uiso 1 1 calc R . . H17B H 0.5678 0.3839 0.5804 0.055 Uiso 1 1 calc R . . C18 C 0.4272(4) 0.4216(4) 0.5435(2) 0.0565(14) Uani 1 1 d . . . H18C H 0.4120 0.4140 0.5095 0.068 Uiso 0.50 1 calc PR A 2 H18D H 0.4530 0.4867 0.5503 0.068 Uiso 0.50 1 calc PR A 2 H18A H 0.4358 0.4374 0.5110 0.068 Uiso 0.50 1 calc PR A 1 H18B H 0.4311 0.4803 0.5622 0.068 Uiso 0.50 1 calc PR A 1 C20 C 0.3470(4) 0.3172(4) 0.5917(2) 0.0553(14) Uani 1 1 d . . . H20C H 0.3014 0.2665 0.5767 0.066 Uiso 0.50 1 calc PR B 2 H20D H 0.3287 0.3261 0.6235 0.066 Uiso 0.50 1 calc PR B 2 H20A H 0.3359 0.3587 0.6181 0.066 Uiso 0.50 1 calc PR B 1 H20B H 0.3009 0.2609 0.5921 0.066 Uiso 0.50 1 calc PR B 1 C19A C 0.3292(12) 0.4026(11) 0.5663(6) 0.056(4) Uani 0.50 1 d P C 2 H19A H 0.3163 0.4553 0.5873 0.068 Uiso 0.50 1 calc PR C 2 H19B H 0.2670 0.3961 0.5426 0.068 Uiso 0.50 1 calc PR C 2 C19 C 0.3257(10) 0.3693(10) 0.5465(5) 0.045(3) Uani 0.50 1 d P C 1 H19C H 0.3101 0.3248 0.5203 0.054 Uiso 0.50 1 calc PR C 1 H19D H 0.2660 0.4138 0.5467 0.054 Uiso 0.50 1 calc PR C 1 C14 C 0.7133(5) -0.0409(6) 0.6993(3) 0.102(3) Uani 1 1 d . . . H14A H 0.7568 -0.0908 0.6872 0.123 Uiso 1 1 calc R . . H14B H 0.7489 -0.0199 0.7298 0.123 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 Al1 0.0231(5) 0.0238(6) 0.0229(5) -0.0002(4) 0.0021(4) -0.0036(4) N1 0.0276(16) 0.0270(17) 0.0263(15) -0.0014(13) 0.0014(12) -0.0043(13) N2 0.0292(16) 0.0237(16) 0.0257(14) 0.0003(13) 0.0042(12) -0.0017(13) O1 0.0297(14) 0.0296(15) 0.0241(13) -0.0009(11) 0.0032(10) -0.0039(11) O2 0.0242(13) 0.0306(14) 0.0273(13) -0.0007(11) 0.0022(10) -0.0057(11) O3 0.0268(13) 0.0278(15) 0.0361(14) 0.0058(12) 0.0030(10) -0.0001(11) O4 0.0285(14) 0.0284(15) 0.0336(14) 0.0056(11) 0.0012(11) -0.0008(11) I1 0.0336(2) 0.0532(3) 0.0522(2) 0.00825(13) 0.00689(14) -0.00262(12) C1 0.0227(17) 0.031(2) 0.0296(18) 0.0038(16) 0.0049(14) 0.0021(15) C2 0.0277(19) 0.036(2) 0.0326(19) 0.0044(17) 0.0056(15) -0.0031(17) C3 0.0297(19) 0.026(2) 0.0339(19) 0.0040(17) 0.0028(15) -0.0024(16) C4 0.038(2) 0.037(2) 0.030(2) -0.0003(17) 0.0082(17) 0.0044(18) C5 0.032(2) 0.049(3) 0.045(2) -0.004(2) -0.0005(17) -0.010(2) C6 0.033(2) 0.037(2) 0.0298(18) -0.0051(17) 0.0029(15) -0.0103(18) C7 0.039(2) 0.031(2) 0.0286(18) -0.0045(17) 0.0068(16) -0.0062(18) C8 0.030(2) 0.030(2) 0.031(2) 0.0053(16) -0.0022(16) -0.0053(16) C9 0.0238(19) 0.030(2) 0.038(2) 0.0018(17) 0.0068(16) -0.0046(16) C10 0.0296(19) 0.028(2) 0.0280(18) 0.0065(16) 0.0007(14) 0.0015(16) C11 0.039(2) 0.049(3) 0.040(2) -0.001(2) 0.0000(18) -0.018(2) C12 0.037(2) 0.030(2) 0.039(2) 0.0009(18) 0.0122(17) 0.0008(18) C13 0.031(2) 0.041(3) 0.060(3) 0.013(2) 0.0094(19) 0.0128(19) C15 0.057(3) 0.059(4) 0.080(4) 0.035(3) 0.008(3) 0.005(3) C16 0.042(3) 0.055(4) 0.112(5) 0.052(4) 0.006(3) -0.005(3) C17 0.036(2) 0.042(3) 0.060(3) 0.024(2) 0.009(2) -0.003(2) C18 0.045(3) 0.053(3) 0.072(3) 0.031(3) 0.010(2) 0.004(2) C20 0.023(2) 0.061(3) 0.084(4) 0.031(3) 0.013(2) 0.011(2) C19A 0.050(7) 0.042(9) 0.083(11) 0.026(7) 0.031(8) 0.014(6) C19 0.035(5) 0.036(7) 0.062(8) 0.016(5) -0.007(6) 0.011(5) C14 0.041(3) 0.096(6) 0.167(8) 0.089(6) 0.003(4) 0.010(3) _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 Al1 O2 1.810(3) . ? Al1 O1 1.817(3) . ? Al1 N1 1.958(3) . ? Al1 N2 1.958(3) . ? Al1 O4 2.000(3) . ? Al1 O3 2.035(3) . ? N1 C3 1.311(5) . ? N1 C6 1.473(5) . ? N2 C10 1.318(5) . ? N2 C7 1.460(5) . ? O1 C1 1.304(5) . ? O2 C8 1.302(5) . ? O3 C16 1.432(6) . ? O3 C13 1.452(5) . ? O4 C20 1.441(5) . ? O4 C17 1.454(5) . ? C1 C2 1.374(6) . ? C1 C4 1.490(6) . ? C2 C3 1.425(6) . ? C2 H2 0.9500 . ? C3 C5 1.502(6) . ? 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 C7 1.510(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.367(6) . ? C8 C11 1.496(6) . ? C9 C10 1.422(6) . ? C9 H9 0.9500 . ? C10 C12 1.508(6) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.473(8) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C15 C14 1.431(9) . ? C15 C16 1.440(8) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.481(7) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.505(15) . ? C18 C19A 1.514(14) . ? C18 H18C 0.9900 . ? C18 H18D 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C20 C19A 1.419(15) . ? C20 C19 1.504(14) . ? C20 H20C 0.9900 . ? C20 H20D 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C19A H19A 0.9900 . ? C19A H19B 0.9900 . ? C19 H19C 0.9900 . ? C19 H19D 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? 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 Al1 O1 91.33(13) . . ? O2 Al1 N1 176.73(14) . . ? O1 Al1 N1 91.67(13) . . ? O2 Al1 N2 92.51(13) . . ? O1 Al1 N2 175.63(14) . . ? N1 Al1 N2 84.53(14) . . ? O2 Al1 O4 90.69(13) . . ? O1 Al1 O4 91.86(13) . . ? N1 Al1 O4 87.93(13) . . ? N2 Al1 O4 90.17(13) . . ? O2 Al1 O3 90.62(13) . . ? O1 Al1 O3 89.48(12) . . ? N1 Al1 O3 90.69(13) . . ? N2 Al1 O3 88.41(13) . . ? O4 Al1 O3 178.11(13) . . ? C3 N1 C6 119.6(3) . . ? C3 N1 Al1 127.2(3) . . ? C6 N1 Al1 112.4(2) . . ? C10 N2 C7 119.5(3) . . ? C10 N2 Al1 126.6(3) . . ? C7 N2 Al1 113.6(2) . . ? C1 O1 Al1 131.0(3) . . ? C8 O2 Al1 129.8(3) . . ? C16 O3 C13 108.1(3) . . ? C16 O3 Al1 125.9(3) . . ? C13 O3 Al1 125.5(2) . . ? C20 O4 C17 108.6(3) . . ? C20 O4 Al1 125.2(3) . . ? C17 O4 Al1 126.1(3) . . ? O1 C1 C2 123.4(3) . . ? O1 C1 C4 114.8(4) . . ? C2 C1 C4 121.8(4) . . ? C1 C2 C3 124.8(4) . . ? C1 C2 H2 117.6 . . ? C3 C2 H2 117.6 . . ? N1 C3 C2 121.5(4) . . ? N1 C3 C5 121.3(4) . . ? C2 C3 C5 117.2(4) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C7 110.1(3) . . ? N1 C6 H6A 109.6 . . ? C7 C6 H6A 109.6 . . ? N1 C6 H6B 109.6 . . ? C7 C6 H6B 109.6 . . ? H6A C6 H6B 108.2 . . ? N2 C7 C6 109.6(3) . . ? N2 C7 H7A 109.8 . . ? C6 C7 H7A 109.8 . . ? N2 C7 H7B 109.8 . . ? C6 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? O2 C8 C9 124.6(4) . . ? O2 C8 C11 114.2(4) . . ? C9 C8 C11 121.2(4) . . ? C8 C9 C10 124.8(4) . . ? C8 C9 H9 117.6 . . ? C10 C9 H9 117.6 . . ? N2 C10 C9 121.5(4) . . ? N2 C10 C12 120.7(4) . . ? C9 C10 C12 117.8(4) . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O3 C13 C14 105.6(4) . . ? O3 C13 H13A 110.6 . . ? C14 C13 H13A 110.6 . . ? O3 C13 H13B 110.6 . . ? C14 C13 H13B 110.6 . . ? H13A C13 H13B 108.7 . . ? C14 C15 C16 107.9(5) . . ? C14 C15 H15A 110.1 . . ? C16 C15 H15A 110.1 . . ? C14 C15 H15B 110.1 . . ? C16 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? O3 C16 C15 108.3(4) . . ? O3 C16 H16A 110.0 . . ? C15 C16 H16A 110.0 . . ? O3 C16 H16B 110.0 . . ? C15 C16 H16B 110.0 . . ? H16A C16 H16B 108.4 . . ? O4 C17 C18 107.4(4) . . ? O4 C17 H17A 110.2 . . ? C18 C17 H17A 110.2 . . ? O4 C17 H17B 110.2 . . ? C18 C17 H17B 110.2 . . ? H17A C17 H17B 108.5 . . ? C17 C18 C19 101.8(6) . . ? C17 C18 C19A 106.2(6) . . ? C19 C18 C19A 28.5(6) . . ? C17 C18 H18C 110.5 . . ? C19 C18 H18C 86.7 . . ? C19A C18 H18C 110.5 . . ? C17 C18 H18D 110.5 . . ? C19 C18 H18D 135.5 . . ? C19A C18 H18D 110.5 . . ? H18C C18 H18D 108.7 . . ? C17 C18 H18A 111.4 . . ? C19 C18 H18A 111.4 . . ? C19A C18 H18A 130.9 . . ? H18C C18 H18A 26.1 . . ? H18D C18 H18A 84.7 . . ? C17 C18 H18B 111.4 . . ? C19 C18 H18B 111.4 . . ? C19A C18 H18B 84.0 . . ? H18C C18 H18B 129.0 . . ? H18D C18 H18B 28.0 . . ? H18A C18 H18B 109.3 . . ? C19A C20 O4 109.8(7) . . ? C19A C20 C19 29.2(6) . . ? O4 C20 C19 103.5(6) . . ? C19A C20 H20C 109.7 . . ? O4 C20 H20C 109.7 . . ? C19 C20 H20C 86.3 . . ? C19A C20 H20D 109.7 . . ? O4 C20 H20D 109.7 . . ? C19 C20 H20D 135.9 . . ? H20C C20 H20D 108.2 . . ? C19A C20 H20A 82.5 . . ? O4 C20 H20A 111.1 . . ? C19 C20 H20A 111.1 . . ? H20C C20 H20A 129.7 . . ? H20D C20 H20A 29.2 . . ? C19A C20 H20B 129.1 . . ? O4 C20 H20B 111.1 . . ? C19 C20 H20B 111.1 . . ? H20C C20 H20B 26.6 . . ? H20D C20 H20B 83.3 . . ? H20A C20 H20B 109.0 . . ? C20 C19A C18 107.0(9) . . ? C20 C19A H19A 110.3 . . ? C18 C19A H19A 110.3 . . ? C20 C19A H19B 110.3 . . ? C18 C19A H19B 110.3 . . ? H19A C19A H19B 108.6 . . ? C18 C19 C20 103.2(8) . . ? C18 C19 H19C 111.1 . . ? C20 C19 H19C 111.1 . . ? C18 C19 H19D 111.1 . . ? C20 C19 H19D 111.1 . . ? H19C C19 H19D 109.1 . . ? C15 C14 C13 107.8(5) . . ? C15 C14 H14A 110.2 . . ? C13 C14 H14A 110.2 . . ? C15 C14 H14B 110.2 . . ? C13 C14 H14B 110.2 . . ? H14A C14 H14B 108.5 . . ? 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 O2 Al1 N1 C3 -156(3) . . . . ? O1 Al1 N1 C3 1.3(4) . . . . ? N2 Al1 N1 C3 179.1(4) . . . . ? O4 Al1 N1 C3 -90.5(3) . . . . ? O3 Al1 N1 C3 90.8(3) . . . . ? O2 Al1 N1 C6 14(3) . . . . ? O1 Al1 N1 C6 170.7(3) . . . . ? N2 Al1 N1 C6 -11.5(3) . . . . ? O4 Al1 N1 C6 78.9(3) . . . . ? O3 Al1 N1 C6 -99.8(3) . . . . ? O2 Al1 N2 C10 -0.3(3) . . . . ? O1 Al1 N2 C10 -151.9(17) . . . . ? N1 Al1 N2 C10 178.3(3) . . . . ? O4 Al1 N2 C10 90.4(3) . . . . ? O3 Al1 N2 C10 -90.8(3) . . . . ? O2 Al1 N2 C7 173.0(3) . . . . ? O1 Al1 N2 C7 21(2) . . . . ? N1 Al1 N2 C7 -8.4(3) . . . . ? O4 Al1 N2 C7 -96.3(3) . . . . ? O3 Al1 N2 C7 82.4(3) . . . . ? O2 Al1 O1 C1 -178.7(3) . . . . ? N1 Al1 O1 C1 2.6(3) . . . . ? N2 Al1 O1 C1 -27(2) . . . . ? O4 Al1 O1 C1 90.6(3) . . . . ? O3 Al1 O1 C1 -88.1(3) . . . . ? O1 Al1 O2 C8 178.4(3) . . . . ? N1 Al1 O2 C8 -25(3) . . . . ? N2 Al1 O2 C8 0.5(4) . . . . ? O4 Al1 O2 C8 -89.7(3) . . . . ? O3 Al1 O2 C8 88.9(3) . . . . ? O2 Al1 O3 C16 145.5(5) . . . . ? O1 Al1 O3 C16 54.1(5) . . . . ? N1 Al1 O3 C16 -37.5(5) . . . . ? N2 Al1 O3 C16 -122.0(5) . . . . ? O4 Al1 O3 C16 -81(4) . . . . ? O2 Al1 O3 C13 -43.2(3) . . . . ? O1 Al1 O3 C13 -134.6(3) . . . . ? N1 Al1 O3 C13 133.8(3) . . . . ? N2 Al1 O3 C13 49.2(3) . . . . ? O4 Al1 O3 C13 90(4) . . . . ? O2 Al1 O4 C20 -132.3(4) . . . . ? O1 Al1 O4 C20 -41.0(4) . . . . ? N1 Al1 O4 C20 50.6(4) . . . . ? N2 Al1 O4 C20 135.2(4) . . . . ? O3 Al1 O4 C20 94(4) . . . . ? O2 Al1 O4 C17 52.6(4) . . . . ? O1 Al1 O4 C17 143.9(4) . . . . ? N1 Al1 O4 C17 -124.5(4) . . . . ? N2 Al1 O4 C17 -39.9(4) . . . . ? O3 Al1 O4 C17 -81(4) . . . . ? Al1 O1 C1 C2 -1.5(6) . . . . ? Al1 O1 C1 C4 178.6(3) . . . . ? O1 C1 C2 C3 -4.0(7) . . . . ? C4 C1 C2 C3 175.9(4) . . . . ? C6 N1 C3 C2 -174.7(4) . . . . ? Al1 N1 C3 C2 -5.9(6) . . . . ? C6 N1 C3 C5 4.2(6) . . . . ? Al1 N1 C3 C5 173.0(3) . . . . ? C1 C2 C3 N1 7.7(7) . . . . ? C1 C2 C3 C5 -171.2(4) . . . . ? C3 N1 C6 C7 -161.5(4) . . . . ? Al1 N1 C6 C7 28.2(4) . . . . ? C10 N2 C7 C6 -160.5(3) . . . . ? Al1 N2 C7 C6 25.7(4) . . . . ? N1 C6 C7 N2 -34.3(5) . . . . ? Al1 O2 C8 C9 1.2(6) . . . . ? Al1 O2 C8 C11 -177.6(3) . . . . ? O2 C8 C9 C10 -3.4(7) . . . . ? C11 C8 C9 C10 175.2(4) . . . . ? C7 N2 C10 C9 -174.4(4) . . . . ? Al1 N2 C10 C9 -1.5(6) . . . . ? C7 N2 C10 C12 5.6(5) . . . . ? Al1 N2 C10 C12 178.5(3) . . . . ? C8 C9 C10 N2 3.5(7) . . . . ? C8 C9 C10 C12 -176.5(4) . . . . ? C16 O3 C13 C14 -14.4(7) . . . . ? Al1 O3 C13 C14 173.0(5) . . . . ? C13 O3 C16 C15 8.7(7) . . . . ? Al1 O3 C16 C15 -178.7(4) . . . . ? C14 C15 C16 O3 0.8(9) . . . . ? C20 O4 C17 C18 2.8(6) . . . . ? Al1 O4 C17 C18 178.6(3) . . . . ? O4 C17 C18 C19 -25.5(8) . . . . ? O4 C17 C18 C19A 3.5(9) . . . . ? C17 O4 C20 C19A -8.6(10) . . . . ? Al1 O4 C20 C19A 175.6(8) . . . . ? C17 O4 C20 C19 21.2(8) . . . . ? Al1 O4 C20 C19 -154.6(6) . . . . ? O4 C20 C19A C18 10.6(14) . . . . ? C19 C20 C19A C18 -71.6(17) . . . . ? C17 C18 C19A C20 -8.6(13) . . . . ? C19 C18 C19A C20 76.3(17) . . . . ? C17 C18 C19 C20 38.0(9) . . . . ? C19A C18 C19 C20 -64.2(17) . . . . ? C19A C20 C19 C18 69.7(18) . . . . ? O4 C20 C19 C18 -36.9(10) . . . . ? C16 C15 C14 C13 -9.8(10) . . . . ? O3 C13 C14 C15 14.9(9) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 67.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.958 _refine_diff_density_min -0.888 _refine_diff_density_rms 0.107 # Attachment '- 3rev.CIF' data_g:\ltuxra~1\nono~1\ar169g~1\ar169 _database_code_depnum_ccdc_archive 'CCDC 861501' #TrackingRef '- 3rev.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '(NO-NO Ga(Me2)(Cl))2' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H32 Cl2 Ga2 N2 O2' _chemical_formula_weight 494.78 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ga Ga 0.2307 1.6083 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9600(2) _cell_length_b 7.3178(3) _cell_length_c 11.7649(4) _cell_angle_alpha 80.036(3) _cell_angle_beta 88.925(3) _cell_angle_gamma 75.353(3) _cell_volume 570.79(3) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2997 _cell_measurement_theta_min 2.9158 _cell_measurement_theta_max 29.1903 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 254 _exptl_absorpt_coefficient_mu 2.604 _exptl_absorpt_correction_T_min 0.75652 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini' _diffrn_detector_area_resol_mean 10.3281 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12375 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2599 _reflns_number_gt 2306 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material SHELXL-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^)+(0.0296P)^2^+0.2283P] 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 2599 _refine_ls_number_parameters 117 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0654 _refine_ls_wR_factor_gt 0.0617 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 Ga1 Ga 0.54877(3) 0.81015(3) 0.316722(18) 0.02654(9) Uani 1 1 d . . . Cl1 Cl 0.52681(8) 1.07188(8) 0.17720(5) 0.04056(15) Uani 1 1 d . . . O1 O 0.7050(2) 0.6386(2) 0.21806(12) 0.0280(3) Uani 1 1 d . . . N1 N 0.9380(3) 0.7694(2) 0.06028(14) 0.0221(3) Uani 1 1 d . . . C1 C 0.8521(3) 0.4876(3) 0.24531(16) 0.0251(4) Uani 1 1 d . . . H1 H 0.836(3) 0.785(3) 0.0911(19) 0.022(6) Uiso 1 1 d . . . C2 C 1.0274(3) 0.4681(3) 0.18732(17) 0.0253(4) Uani 1 1 d . . . H2B H 1.1265 0.3511 0.2076 0.030 Uiso 1 1 calc R . . C3 C 1.0713(3) 0.6082(3) 0.10039(16) 0.0226(4) Uani 1 1 d . . . C4 C 0.8224(4) 0.3339(3) 0.3404(2) 0.0382(5) Uani 1 1 d . . . H4A H 0.7863 0.3882 0.4107 0.057 Uiso 1 1 calc R . . H4B H 0.9457 0.2319 0.3549 0.057 Uiso 1 1 calc R . . H4C H 0.7157 0.2808 0.3180 0.057 Uiso 1 1 calc R . . C5 C 1.2762(3) 0.5747(3) 0.05244(18) 0.0296(5) Uani 1 1 d . . . H5A H 1.3367 0.6764 0.0661 0.044 Uiso 1 1 calc R . . H5B H 1.2679 0.5756 -0.0307 0.044 Uiso 1 1 calc R . . H5C H 1.3576 0.4501 0.0906 0.044 Uiso 1 1 calc R . . C6 C 0.9657(3) 0.9260(3) -0.02715(16) 0.0240(4) Uani 1 1 d . . . H6A H 0.8390 0.9882 -0.0706 0.029 Uiso 1 1 calc R . . H6B H 1.0657 0.8748 -0.0822 0.029 Uiso 1 1 calc R . . C7 C 0.7300(4) 0.8103(4) 0.4419(2) 0.0424(6) Uani 1 1 d . . . H13A H 0.7145 0.7152 0.5088 0.064 Uiso 1 1 calc R . . H13B H 0.6990 0.9378 0.4635 0.064 Uiso 1 1 calc R . . H13C H 0.8672 0.7779 0.4160 0.064 Uiso 1 1 calc R . . C8 C 0.2849(3) 0.7644(4) 0.33497(19) 0.0382(5) Uani 1 1 d . . . H14A H 0.2974 0.6273 0.3617 0.057 Uiso 1 1 calc R . . H14B H 0.2121 0.8053 0.2607 0.057 Uiso 1 1 calc R . . H14C H 0.2127 0.8375 0.3918 0.057 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 Ga1 0.02293(13) 0.03024(14) 0.02705(14) -0.00578(10) 0.00393(9) -0.00752(9) Cl1 0.0356(3) 0.0273(3) 0.0509(3) 0.0046(2) 0.0048(2) -0.0015(2) O1 0.0269(7) 0.0269(8) 0.0268(7) -0.0023(6) 0.0063(6) -0.0026(6) N1 0.0207(8) 0.0206(8) 0.0241(9) -0.0016(7) 0.0050(7) -0.0053(7) C1 0.0334(11) 0.0219(10) 0.0217(10) -0.0035(8) -0.0011(8) -0.0100(8) C2 0.0274(10) 0.0187(10) 0.0271(10) -0.0010(8) -0.0013(8) -0.0030(8) C3 0.0214(9) 0.0218(10) 0.0246(10) -0.0066(8) 0.0012(8) -0.0038(7) C4 0.0465(14) 0.0316(12) 0.0326(12) 0.0068(10) 0.0048(10) -0.0116(10) C5 0.0263(10) 0.0267(11) 0.0327(11) -0.0043(9) 0.0051(9) -0.0022(8) C6 0.0291(10) 0.0216(10) 0.0201(9) 0.0011(8) 0.0014(8) -0.0075(8) C7 0.0381(13) 0.0508(15) 0.0413(14) -0.0125(12) -0.0041(11) -0.0132(11) C8 0.0317(12) 0.0577(16) 0.0306(12) -0.0093(11) 0.0087(9) -0.0204(11) _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 Ga1 C8 1.950(2) . ? Ga1 C7 1.957(2) . ? Ga1 O1 1.9679(13) . ? Ga1 Cl1 2.2714(6) . ? O1 C1 1.299(2) . ? N1 C3 1.321(2) . ? N1 C6 1.450(2) . ? N1 H1 0.78(2) . ? C1 C2 1.375(3) . ? C1 C4 1.495(3) . ? C2 C3 1.405(3) . ? C2 H2B 0.9500 . ? C3 C5 1.501(3) . ? 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 C6 1.524(4) 2_775 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H13A 0.9800 . ? C7 H13B 0.9800 . ? C7 H13C 0.9800 . ? C8 H14A 0.9800 . ? C8 H14B 0.9800 . ? C8 H14C 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 C8 Ga1 C7 125.92(10) . . ? C8 Ga1 O1 109.33(8) . . ? C7 Ga1 O1 105.91(8) . . ? C8 Ga1 Cl1 107.99(8) . . ? C7 Ga1 Cl1 110.44(8) . . ? O1 Ga1 Cl1 91.90(4) . . ? C1 O1 Ga1 129.76(13) . . ? C3 N1 C6 127.24(17) . . ? C3 N1 H1 115.7(16) . . ? C6 N1 H1 116.9(16) . . ? O1 C1 C2 121.25(18) . . ? O1 C1 C4 117.63(18) . . ? C2 C1 C4 121.11(19) . . ? C1 C2 C3 124.95(18) . . ? C1 C2 H2B 117.5 . . ? C3 C2 H2B 117.5 . . ? N1 C3 C2 121.95(17) . . ? N1 C3 C5 118.98(17) . . ? C2 C3 C5 119.06(17) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C6 111.06(19) . 2_775 ? N1 C6 H6A 109.4 . . ? C6 C6 H6A 109.4 2_775 . ? N1 C6 H6B 109.4 . . ? C6 C6 H6B 109.4 2_775 . ? H6A C6 H6B 108.0 . . ? Ga1 C7 H13A 109.5 . . ? Ga1 C7 H13B 109.5 . . ? H13A C7 H13B 109.5 . . ? Ga1 C7 H13C 109.5 . . ? H13A C7 H13C 109.5 . . ? H13B C7 H13C 109.5 . . ? Ga1 C8 H14A 109.5 . . ? Ga1 C8 H14B 109.5 . . ? H14A C8 H14B 109.5 . . ? Ga1 C8 H14C 109.5 . . ? H14A C8 H14C 109.5 . . ? H14B C8 H14C 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 C8 Ga1 O1 C1 -107.22(18) . . . . ? C7 Ga1 O1 C1 31.07(19) . . . . ? Cl1 Ga1 O1 C1 142.96(16) . . . . ? Ga1 O1 C1 C2 -128.65(17) . . . . ? Ga1 O1 C1 C4 52.6(2) . . . . ? O1 C1 C2 C3 4.1(3) . . . . ? C4 C1 C2 C3 -177.20(19) . . . . ? C6 N1 C3 C2 178.72(17) . . . . ? C6 N1 C3 C5 -0.7(3) . . . . ? C1 C2 C3 N1 -5.1(3) . . . . ? C1 C2 C3 C5 174.22(19) . . . . ? C3 N1 C6 C6 -90.4(3) . . . 2_775 ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.339 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.064 # Attachment '- 4.cif' data_ar155a _database_code_depnum_ccdc_archive 'CCDC 861502' #TrackingRef '- 4.cif' _audit_creation_date 2011-01-28 _audit_creation_method ; Olex2 1.1 (compiled 2011.01.21 svn.r1625, GUI svn.r3464) ; _chemical_name_common nonoHaCl _chemical_name_systematic nonoHaCl _chemical_formula_moiety '2(C12 H18 Cl Ga Li N2 O2), 2(Cl2 Ga)' _chemical_formula_sum 'C24 H36 Cl6 Ga3 Li N4 O4' _chemical_formula_weight 873.37 _chemical_melting_point ? _chemical_oxdiff_formula 'C12 H12 N1 O3 GA1 CL1' 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' Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 56 _space_group_name_H-M_alt 'P c c n' _space_group_name_Hall '-P 2ab 2ac' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y+1/2, z' 3 'x+1/2, -y, -z+1/2' 4 '-x, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y-1/2, -z' 7 '-x-1/2, y, z-1/2' 8 'x, -y-1/2, z-1/2' _cell_length_a 11.0058(5) _cell_length_b 19.6503(9) _cell_length_c 16.5196(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3572.6(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1687 _cell_measurement_temperature 173.2 _cell_measurement_theta_max 29.2757 _cell_measurement_theta_min 3.0344 _exptl_absorpt_coefficient_mu 2.729 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.72795 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_modifier yellowish _exptl_crystal_colour_primary ? _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1752 _exptl_crystal_preparation 'paratone oil' _exptl_crystal_recrystallization_method 'anaerobic techniques, from concentration of a thf solution' _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_unetI/netI 0.0263 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 35029 _diffrn_reflns_theta_full 26.25 _diffrn_reflns_theta_max 29.48 _diffrn_reflns_theta_min 2.45 _diffrn_ambient_temperature 173.2 _diffrn_detector_area_resol_mean 10.3281 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.924 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 22.00 47.00 1.0000 46.0000 omega____ theta____ kappa____ phi______ frames - 11.2472 -85.0000 -42.0000 25 #__ type_ start__ end____ width___ exp.time_ 2 omega -85.00 -60.00 1.0000 46.0000 omega____ theta____ kappa____ phi______ frames - -12.0285 -38.0000 30.0000 25 ; _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0157068000 _diffrn_orient_matrix_UB_12 0.0304454000 _diffrn_orient_matrix_UB_13 0.0204911000 _diffrn_orient_matrix_UB_21 -0.0375977000 _diffrn_orient_matrix_UB_22 0.0095779000 _diffrn_orient_matrix_UB_23 -0.0330272000 _diffrn_orient_matrix_UB_31 -0.0499585000 _diffrn_orient_matrix_UB_32 -0.0167958000 _diffrn_orient_matrix_UB_33 0.0182985000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_special_details 'collected as triclinic' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3610 _reflns_number_total 4602 _reflns_odcompleteness_completeness 56.87 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)' _refine_diff_density_max 0.693 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.085 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 195 _refine_ls_number_reflns 4602 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0367 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+4.6924P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0805 _refine_ls_wR_factor_ref 0.0894 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Ga1 Ga 0.60749(2) 0.377265(14) 0.164788(17) 0.02302(9) Uani 1 1 d . . . Ga2 Ga 0.2500 0.2500 0.26224(3) 0.03655(13) Uani 1 2 d S . . Cl1 Cl 0.72502(7) 0.44282(4) 0.08954(5) 0.03993(18) Uani 1 1 d . . . Cl2 Cl 0.15582(8) 0.32582(6) 0.19096(6) 0.0655(3) Uani 1 1 d . . . Cl3 Cl 0.38291(7) 0.30171(4) 0.33720(5) 0.04323(19) Uani 1 1 d . . . O1 O 0.61155(15) 0.28759(9) 0.11944(10) 0.0245(4) Uani 1 1 d . . . O2 O 0.72802(16) 0.33577(9) 0.23434(11) 0.0284(4) Uani 1 1 d . . . N1 N 0.4484(2) 0.39546(12) 0.11474(14) 0.0301(5) Uani 1 1 d . . . N2 N 0.5435(2) 0.43295(11) 0.25397(14) 0.0281(5) Uani 1 1 d . . . C1 C 0.5439(2) 0.26542(14) 0.05938(15) 0.0266(5) Uani 1 1 d . . . C2 C 0.4484(2) 0.30007(14) 0.02702(16) 0.0293(6) Uani 1 1 d . . . H2 H 0.4102 0.2802 -0.0188 0.035 Uiso 1 1 calc R . . C3 C 0.3998(2) 0.36305(14) 0.05473(16) 0.0290(6) Uani 1 1 d . . . C4 C 0.5797(3) 0.19731(15) 0.02841(19) 0.0389(7) Uani 1 1 d . . . H4A H 0.6643 0.1987 0.0100 0.058 Uiso 1 1 calc R . . H4B H 0.5269 0.1847 -0.0170 0.058 Uiso 1 1 calc R . . H4C H 0.5714 0.1636 0.0718 0.058 Uiso 1 1 calc R . . C5 C 0.2905(3) 0.38984(17) 0.01056(19) 0.0411(7) Uani 1 1 d . . . H5A H 0.2198 0.3889 0.0466 0.062 Uiso 1 1 calc R . . H5B H 0.2745 0.3614 -0.0370 0.062 Uiso 1 1 calc R . . H5C H 0.3058 0.4367 -0.0068 0.062 Uiso 1 1 calc R . . C6 C 0.4009(3) 0.45988(16) 0.1454(2) 0.0400(7) Uani 1 1 d . . . H6A H 0.3127 0.4630 0.1345 0.048 Uiso 1 1 calc R . . H6B H 0.4417 0.4984 0.1180 0.048 Uiso 1 1 calc R . . C7 C 0.4240(3) 0.46327(16) 0.2356(2) 0.0387(7) Uani 1 1 d . . . H7A H 0.4224 0.5113 0.2538 0.046 Uiso 1 1 calc R . . H7B H 0.3595 0.4382 0.2648 0.046 Uiso 1 1 calc R . . C8 C 0.7609(2) 0.35771(14) 0.30625(16) 0.0266(5) Uani 1 1 d . . . C9 C 0.6998(2) 0.40518(13) 0.34913(16) 0.0278(6) Uani 1 1 d . . . H9 H 0.7333 0.4177 0.4000 0.033 Uiso 1 1 calc R . . C10 C 0.5902(2) 0.43831(14) 0.32598(16) 0.0284(6) Uani 1 1 d . . . C11 C 0.8727(3) 0.32414(18) 0.33879(19) 0.0408(7) Uani 1 1 d . . . H11A H 0.8612 0.2747 0.3393 0.061 Uiso 1 1 calc R . . H11B H 0.8879 0.3402 0.3940 0.061 Uiso 1 1 calc R . . H11C H 0.9423 0.3356 0.3044 0.061 Uiso 1 1 calc R . . C12 C 0.5272(3) 0.48002(19) 0.3903(2) 0.0481(8) Uani 1 1 d . . . H12A H 0.5205 0.5273 0.3721 0.072 Uiso 1 1 calc R . . H12B H 0.5744 0.4783 0.4405 0.072 Uiso 1 1 calc R . . H12C H 0.4458 0.4615 0.4000 0.072 Uiso 1 1 calc R . . Li1 Li 0.7500 0.2500 0.1775(4) 0.0284(13) Uani 1 2 d S . . 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 Ga1 0.02094(14) 0.02186(15) 0.02627(15) -0.00062(11) -0.00088(11) 0.00481(10) Ga2 0.0259(2) 0.0575(3) 0.0262(2) 0.000 0.000 -0.0082(2) Cl1 0.0387(4) 0.0328(4) 0.0483(4) 0.0087(3) 0.0087(3) -0.0009(3) Cl2 0.0408(5) 0.1021(8) 0.0536(5) 0.0329(5) -0.0141(4) -0.0086(5) Cl3 0.0381(4) 0.0484(5) 0.0433(4) 0.0022(3) -0.0134(3) -0.0073(3) O1 0.0229(9) 0.0246(9) 0.0261(9) -0.0041(7) -0.0035(7) 0.0057(7) O2 0.0280(10) 0.0299(10) 0.0273(9) -0.0047(8) -0.0048(7) 0.0099(8) N1 0.0257(11) 0.0283(12) 0.0364(13) 0.0003(10) -0.0031(10) 0.0089(9) N2 0.0263(11) 0.0237(11) 0.0344(12) -0.0049(9) 0.0024(9) 0.0038(9) C1 0.0274(13) 0.0303(14) 0.0222(12) -0.0018(10) 0.0015(10) 0.0014(10) C2 0.0285(14) 0.0352(15) 0.0240(13) -0.0018(11) -0.0043(11) 0.0023(11) C3 0.0248(13) 0.0348(15) 0.0274(13) 0.0074(11) -0.0022(10) 0.0041(11) C4 0.0426(17) 0.0371(17) 0.0370(16) -0.0126(13) -0.0071(13) 0.0099(13) C5 0.0378(17) 0.0447(18) 0.0408(17) 0.0074(14) -0.0113(14) 0.0112(13) C6 0.0377(16) 0.0318(16) 0.0507(18) -0.0035(14) -0.0079(14) 0.0163(13) C7 0.0327(15) 0.0345(16) 0.0487(18) -0.0059(14) -0.0003(13) 0.0156(12) C8 0.0260(13) 0.0268(13) 0.0269(13) 0.0035(10) -0.0041(10) -0.0043(10) C9 0.0291(13) 0.0285(14) 0.0258(13) -0.0020(10) -0.0022(10) -0.0066(11) C10 0.0293(13) 0.0242(13) 0.0318(14) -0.0064(11) 0.0058(11) -0.0042(11) C11 0.0345(16) 0.0488(19) 0.0391(17) -0.0002(14) -0.0144(13) 0.0063(13) C12 0.0441(18) 0.053(2) 0.0466(19) -0.0220(16) 0.0041(15) 0.0058(15) Li1 0.026(3) 0.032(3) 0.027(3) 0.000 0.000 0.011(3) _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 Ga1 Cl1 2.2087(8) . ? Ga1 O1 1.9152(17) . ? Ga1 O2 1.9351(18) . ? Ga1 N1 1.969(2) . ? Ga1 N2 1.966(2) . ? Ga2 Cl2 2.1635(10) 2 ? Ga2 Cl2 2.1635(10) . ? Ga2 Cl3 2.1693(8) . ? Ga2 Cl3 2.1693(8) 2 ? O1 C1 1.315(3) . ? O1 Li1 1.947(4) . ? O2 C8 1.315(3) . ? O2 Li1 1.944(3) . ? N1 C3 1.294(4) . ? N1 C6 1.460(4) . ? N2 C7 1.476(3) . ? N2 C10 1.300(3) . ? C1 C2 1.362(4) . ? C1 C4 1.486(4) . ? C2 H2 0.9500 . ? C2 C3 1.424(4) . ? C3 C5 1.503(4) . ? 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 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.512(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.351(4) . ? C8 C11 1.496(4) . ? C9 H9 0.9500 . ? C9 C10 1.422(4) . ? C10 C12 1.510(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? Li1 Ga1 2.9594(5) 2_655 ? Li1 O1 1.947(3) 2_655 ? Li1 O2 1.944(3) 2_655 ? 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 O1 Ga1 Cl1 107.63(6) . . ? O1 Ga1 O2 80.13(7) . . ? O1 Ga1 N1 91.35(9) . . ? O1 Ga1 N2 144.46(9) . . ? O2 Ga1 Cl1 100.28(6) . . ? O2 Ga1 N1 159.30(9) . . ? O2 Ga1 N2 92.01(8) . . ? N1 Ga1 Cl1 100.28(7) . . ? N2 Ga1 Cl1 107.87(7) . . ? N2 Ga1 N1 83.98(10) . . ? Cl2 Ga2 Cl2 114.05(7) . 2 ? Cl2 Ga2 Cl3 108.07(3) 2 . ? Cl2 Ga2 Cl3 108.13(4) . . ? Cl2 Ga2 Cl3 108.13(4) 2 2 ? Cl2 Ga2 Cl3 108.07(3) . 2 ? Cl3 Ga2 Cl3 110.38(5) 2 . ? Ga1 O1 Li1 100.05(12) . . ? C1 O1 Ga1 125.93(16) . . ? C1 O1 Li1 133.60(19) . . ? Ga1 O2 Li1 99.44(15) . . ? C8 O2 Ga1 125.97(17) . . ? C8 O2 Li1 133.3(2) . . ? C3 N1 Ga1 126.84(19) . . ? C3 N1 C6 123.0(2) . . ? C6 N1 Ga1 109.26(18) . . ? C7 N2 Ga1 112.93(18) . . ? C10 N2 Ga1 126.10(19) . . ? C10 N2 C7 120.5(2) . . ? O1 C1 C2 124.6(2) . . ? O1 C1 C4 114.1(2) . . ? C2 C1 C4 121.3(2) . . ? C1 C2 H2 116.6 . . ? C1 C2 C3 126.7(3) . . ? C3 C2 H2 116.6 . . ? N1 C3 C2 121.3(2) . . ? N1 C3 C5 122.0(3) . . ? C2 C3 C5 116.7(3) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4B 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5B 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 H6A 110.0 . . ? N1 C6 H6B 110.0 . . ? N1 C6 C7 108.7(2) . . ? H6A C6 H6B 108.3 . . ? C7 C6 H6A 110.0 . . ? C7 C6 H6B 110.0 . . ? N2 C7 C6 109.6(2) . . ? N2 C7 H7A 109.8 . . ? N2 C7 H7B 109.8 . . ? C6 C7 H7A 109.8 . . ? C6 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? O2 C8 C9 124.3(2) . . ? O2 C8 C11 114.0(2) . . ? C9 C8 C11 121.7(3) . . ? C8 C9 H9 116.7 . . ? C8 C9 C10 126.7(2) . . ? C10 C9 H9 116.7 . . ? N2 C10 C9 123.0(2) . . ? N2 C10 C12 120.4(3) . . ? C9 C10 C12 116.6(3) . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O1 Li1 Ga1 39.58(5) 2_655 2_655 ? O1 Li1 Ga1 134.5(2) . 2_655 ? O1 Li1 O1 120.9(3) 2_655 . ? O2 Li1 Ga1 40.17(6) 2_655 2_655 ? O2 Li1 Ga1 146.4(2) . 2_655 ? O2 Li1 O1 79.14(7) 2_655 2_655 ? O2 Li1 O1 131.64(8) . 2_655 ? O2 Li1 O1 79.14(7) . . ? O2 Li1 O1 131.64(8) 2_655 . ? O2 Li1 O2 122.3(3) 2_655 . ? 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 Ga1 O1 C1 C2 -9.4(4) . . . . ? Ga1 O1 C1 C4 170.95(19) . . . . ? Ga1 O1 Li1 Ga1 -171.7(2) . . . 2_655 ? Ga1 O1 Li1 O1 -123.86(9) . . . 2_655 ? Ga1 O1 Li1 O2 8.49(14) . . . . ? Ga1 O1 Li1 O2 132.4(3) . . . 2_655 ? Ga1 O2 C8 C9 13.0(4) . . . . ? Ga1 O2 C8 C11 -168.32(19) . . . . ? Ga1 O2 Li1 Ga1 171.9(3) . . . 2_655 ? Ga1 O2 Li1 O1 113.6(3) . . . 2_655 ? Ga1 O2 Li1 O1 -8.39(14) . . . . ? Ga1 O2 Li1 O2 -141.15(9) . . . 2_655 ? Ga1 N1 C3 C2 12.4(4) . . . . ? Ga1 N1 C3 C5 -167.2(2) . . . . ? Ga1 N1 C6 C7 -42.4(3) . . . . ? Ga1 N2 C7 C6 -16.3(3) . . . . ? Ga1 N2 C10 C9 2.3(4) . . . . ? Ga1 N2 C10 C12 -176.5(2) . . . . ? Cl1 Ga1 O1 C1 -84.2(2) . . . . ? Cl1 Ga1 O1 Li1 89.24(15) . . . . ? Cl1 Ga1 O2 C8 93.7(2) . . . . ? Cl1 Ga1 O2 Li1 -97.81(12) . . . . ? Cl1 Ga1 N1 C3 89.3(2) . . . . ? Cl1 Ga1 N1 C6 -80.1(2) . . . . ? Cl1 Ga1 N2 C7 93.35(19) . . . . ? Cl1 Ga1 N2 C10 -94.1(2) . . . . ? O1 Ga1 O2 C8 -160.0(2) . . . . ? O1 Ga1 O2 Li1 8.50(13) . . . . ? O1 Ga1 N1 C3 -18.9(2) . . . . ? O1 Ga1 N1 C6 171.7(2) . . . . ? O1 Ga1 N2 C7 -89.4(2) . . . . ? O1 Ga1 N2 C10 83.1(3) . . . . ? O1 C1 C2 C3 -4.4(5) . . . . ? O2 Ga1 O1 C1 178.0(2) . . . . ? O2 Ga1 O1 Li1 -8.50(15) . . . . ? O2 Ga1 N1 C3 -83.9(3) . . . . ? O2 Ga1 N1 C6 106.7(3) . . . . ? O2 Ga1 N2 C7 -165.2(2) . . . . ? O2 Ga1 N2 C10 7.3(2) . . . . ? O2 C8 C9 C10 1.4(4) . . . . ? N1 Ga1 O1 C1 17.0(2) . . . . ? N1 Ga1 O1 Li1 -169.52(16) . . . . ? N1 Ga1 O2 C8 -93.1(3) . . . . ? N1 Ga1 O2 Li1 75.4(3) . . . . ? N1 Ga1 N2 C7 -5.5(2) . . . . ? N1 Ga1 N2 C10 167.0(2) . . . . ? N1 C6 C7 N2 37.9(3) . . . . ? N2 Ga1 O1 C1 98.5(2) . . . . ? N2 Ga1 O1 Li1 -88.0(2) . . . . ? N2 Ga1 O2 C8 -14.9(2) . . . . ? N2 Ga1 O2 Li1 153.62(14) . . . . ? N2 Ga1 N1 C3 -163.5(3) . . . . ? N2 Ga1 N1 C6 27.0(2) . . . . ? C1 O1 Li1 Ga1 1.0(4) . . . 2_655 ? C1 O1 Li1 O1 48.8(2) . . . 2_655 ? C1 O1 Li1 O2 -178.8(2) . . . . ? C1 O1 Li1 O2 -54.9(5) . . . 2_655 ? C1 C2 C3 N1 2.7(5) . . . . ? C1 C2 C3 C5 -177.7(3) . . . . ? C3 N1 C6 C7 147.7(3) . . . . ? C4 C1 C2 C3 175.2(3) . . . . ? C6 N1 C3 C2 -179.5(3) . . . . ? C6 N1 C3 C5 0.9(4) . . . . ? C7 N2 C10 C9 174.3(3) . . . . ? C7 N2 C10 C12 -4.5(4) . . . . ? C8 O2 Li1 Ga1 -20.9(5) . . . 2_655 ? C8 O2 Li1 O1 -79.2(5) . . . 2_655 ? C8 O2 Li1 O1 158.8(2) . . . . ? C8 O2 Li1 O2 26.0(2) . . . 2_655 ? C8 C9 C10 N2 -9.5(4) . . . . ? C8 C9 C10 C12 169.3(3) . . . . ? C10 N2 C7 C6 170.7(3) . . . . ? C11 C8 C9 C10 -177.2(3) . . . . ? Li1 O1 C1 C2 179.5(3) . . . . ? Li1 O1 C1 C4 -0.2(4) . . . . ? Li1 O2 C8 C9 -151.3(2) . . . . ? Li1 O2 C8 C11 27.4(4) . . . . ? # Attachment '- 7 rev.CIF' data_d:\bono\temp\ar223 _database_code_depnum_ccdc_archive 'CCDC 861504' #TrackingRef '- 7 rev.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ((NO)3In3)0.5PhMe _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H62 In2 N6 O6' _chemical_formula_weight 988.63 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5167(7) _cell_length_b 11.0176(8) _cell_length_c 12.5746(7) _cell_angle_alpha 80.165(6) _cell_angle_beta 80.237(5) _cell_angle_gamma 73.433(7) _cell_volume 1105.15(14) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5831 _cell_measurement_theta_min 2.3815 _cell_measurement_theta_max 29.3813 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 1.095 _exptl_absorpt_correction_T_min 0.98685 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.3281 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10106 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4908 _reflns_number_gt 4396 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material SHELXL-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. A disordered toluene molecule was refined using distant restraints. ; _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^)+(0.0416P)^2^+0.8399P] 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 4908 _refine_ls_number_parameters 292 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0877 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.099 _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 0.98650(3) 0.329567(19) 0.296128(18) 0.01646(8) Uani 1 1 d . . . O1 O 1.1573(3) 0.4387(2) 0.23678(19) 0.0234(5) Uani 1 1 d . . . N1 N 1.0237(3) 0.2803(2) 0.1268(2) 0.0213(6) Uani 1 1 d . . . C1 C 1.2261(4) 0.4579(3) 0.1378(3) 0.0214(7) Uani 1 1 d . . . C20 C 0.6053(10) 0.0372(8) -0.0521(6) 0.0260(19) Uani 0.50 1 d PD A -1 C21 C 0.5139(15) 0.0882(11) 0.0430(8) 0.034(3) Uani 0.50 1 d PD A -1 H21 H 0.5306 0.1618 0.0643 0.041 Uiso 0.50 1 calc PR A -1 C22 C 0.3964(17) 0.0260(11) 0.1056(11) 0.049(4) Uani 0.50 1 d PD A -1 H22 H 0.3396 0.0593 0.1705 0.059 Uiso 0.50 1 calc PR A -1 O2 O 0.7866(3) 0.5018(2) 0.2879(2) 0.0230(5) Uani 1 1 d . . . N2 N 0.7859(3) 0.2419(3) 0.2911(2) 0.0226(6) Uani 1 1 d . . . C2 C 1.2093(4) 0.4088(3) 0.0489(3) 0.0251(7) Uani 1 1 d . . . H2A H 1.2702 0.4344 -0.0175 0.030 Uiso 1 1 calc R . . O3 O 1.1544(3) 0.1433(2) 0.32665(19) 0.0206(5) Uani 1 1 d . . . N3 N 0.9963(3) 0.3395(2) 0.4713(2) 0.0171(5) Uani 1 1 d . . . C3 C 1.1129(4) 0.3243(3) 0.0423(3) 0.0231(7) Uani 1 1 d . . . C4 C 1.3368(5) 0.5477(4) 0.1244(3) 0.0325(8) Uani 1 1 d . . . H4A H 1.3361 0.5744 0.1950 0.049 Uiso 1 1 calc R . . H4B H 1.2959 0.6230 0.0727 0.049 Uiso 1 1 calc R . . H4C H 1.4499 0.5035 0.0970 0.049 Uiso 1 1 calc R . . C5 C 1.1205(5) 0.2865(4) -0.0684(3) 0.0333(8) Uani 1 1 d . . . H5A H 1.0501 0.2287 -0.0636 0.050 Uiso 1 1 calc R . . H5B H 1.2347 0.2432 -0.0942 0.050 Uiso 1 1 calc R . . H5C H 1.0815 0.3630 -0.1195 0.050 Uiso 1 1 calc R . . C6 C 0.9228(5) 0.1970(3) 0.1131(3) 0.0275(8) Uani 1 1 d . . . H6A H 0.9918 0.1273 0.0718 0.033 Uiso 1 1 calc R . . H6B H 0.8319 0.2470 0.0708 0.033 Uiso 1 1 calc R . . C7 C 0.8508(4) 0.1402(3) 0.2233(3) 0.0251(7) Uani 1 1 d . . . H7A H 0.7616 0.1031 0.2142 0.030 Uiso 1 1 calc R . . H7B H 0.9376 0.0716 0.2574 0.030 Uiso 1 1 calc R . . C8 C 0.6373(4) 0.5083(3) 0.3324(3) 0.0253(7) Uani 1 1 d . . . C9 C 0.5640(4) 0.4087(4) 0.3597(3) 0.0297(8) Uani 1 1 d . . . H9A H 0.4613 0.4234 0.4055 0.036 Uiso 1 1 calc R . . C10 C 0.6292(4) 0.2856(3) 0.3250(3) 0.0260(7) Uani 1 1 d . . . C11 C 0.5347(5) 0.6426(4) 0.3478(4) 0.0394(10) Uani 1 1 d . . . H11A H 0.6039 0.7022 0.3244 0.059 Uiso 1 1 calc R . . H11B H 0.4908 0.6461 0.4247 0.059 Uiso 1 1 calc R . . H11C H 0.4430 0.6664 0.3041 0.059 Uiso 1 1 calc R . . C12 C 0.5057(5) 0.2115(4) 0.3253(4) 0.0396(10) Uani 1 1 d . . . H12A H 0.5628 0.1287 0.3003 0.059 Uiso 1 1 calc R . . H12B H 0.4243 0.2595 0.2766 0.059 Uiso 1 1 calc R . . H12C H 0.4494 0.1978 0.3993 0.059 Uiso 1 1 calc R . . C13 C 1.1815(4) 0.0756(3) 0.4182(3) 0.0205(7) Uani 1 1 d . . . C14 C 1.1342(4) 0.1162(3) 0.5187(3) 0.0250(7) Uani 1 1 d . . . H14A H 1.1594 0.0527 0.5793 0.030 Uiso 1 1 calc R . . C15 C 1.0515(4) 0.2424(3) 0.5436(3) 0.0226(7) Uani 1 1 d . . . C16 C 1.2793(5) -0.0615(3) 0.4112(3) 0.0324(8) Uani 1 1 d . . . H16A H 1.2284 -0.1000 0.3661 0.049 Uiso 1 1 calc R . . H16B H 1.2800 -0.1094 0.4844 0.049 Uiso 1 1 calc R . . H16C H 1.3930 -0.0640 0.3786 0.049 Uiso 1 1 calc R . . C17 C 1.0315(5) 0.2574(3) 0.6630(3) 0.0338(9) Uani 1 1 d . . . H17A H 1.0780 0.3265 0.6714 0.051 Uiso 1 1 calc R . . H17B H 1.0896 0.1775 0.7032 0.051 Uiso 1 1 calc R . . H17C H 0.9139 0.2780 0.6917 0.051 Uiso 1 1 calc R . . C18 C 0.9306(4) 0.4672(3) 0.5067(3) 0.0185(6) Uani 1 1 d . . . H18A H 0.8814 0.4593 0.5839 0.022 Uiso 1 1 calc R . . H18B H 0.8431 0.5192 0.4625 0.022 Uiso 1 1 calc R . . C19 C 0.7320(12) 0.0968(10) -0.1207(9) 0.050(3) Uani 0.50 1 d PD A -1 H19A H 0.8005 0.0383 -0.1714 0.075 Uiso 0.50 1 calc PR A -1 H19B H 0.8020 0.1142 -0.0739 0.075 Uiso 0.50 1 calc PR A -1 H19C H 0.6766 0.1770 -0.1619 0.075 Uiso 0.50 1 calc PR A -1 C23 C 0.3561(18) -0.0821(11) 0.0795(9) 0.059(4) Uani 0.50 1 d PD A -1 H23 H 0.2741 -0.1187 0.1227 0.070 Uiso 0.50 1 calc PR A -1 C24 C 0.4494(17) -0.1304(11) -0.0167(10) 0.045(3) Uani 0.50 1 d PD A -1 H24 H 0.4320 -0.2033 -0.0388 0.054 Uiso 0.50 1 calc PR A -1 C25 C 0.5684(13) -0.0703(9) -0.0799(9) 0.026(2) Uani 0.50 1 d PD A -1 H25 H 0.6264 -0.1040 -0.1444 0.031 Uiso 0.50 1 calc PR A -1 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 0.01799(13) 0.01713(12) 0.01471(13) -0.00235(8) -0.00142(8) -0.00555(8) O1 0.0273(12) 0.0288(12) 0.0178(12) -0.0027(10) 0.0010(10) -0.0155(10) N1 0.0296(15) 0.0198(13) 0.0163(14) -0.0018(11) -0.0055(12) -0.0084(11) C1 0.0210(16) 0.0202(15) 0.0209(18) 0.0013(13) -0.0003(13) -0.0058(13) C20 0.029(5) 0.025(5) 0.020(5) -0.005(4) -0.014(4) 0.006(4) C21 0.044(9) 0.029(6) 0.026(7) -0.014(6) -0.012(6) 0.004(6) C22 0.061(9) 0.036(7) 0.034(6) -0.002(6) 0.001(6) 0.007(5) O2 0.0241(12) 0.0197(11) 0.0234(13) -0.0009(9) -0.0034(10) -0.0040(9) N2 0.0237(15) 0.0255(14) 0.0211(15) -0.0011(12) -0.0041(12) -0.0111(12) C2 0.0284(18) 0.0251(17) 0.0183(17) -0.0001(14) 0.0059(14) -0.0084(14) O3 0.0224(12) 0.0196(11) 0.0177(12) -0.0051(9) -0.0026(9) -0.0006(9) N3 0.0202(13) 0.0154(12) 0.0164(14) -0.0048(10) -0.0001(10) -0.0055(10) C3 0.0288(18) 0.0208(16) 0.0157(17) -0.0007(13) -0.0032(14) -0.0011(14) C4 0.034(2) 0.040(2) 0.027(2) -0.0013(16) 0.0026(16) -0.0223(17) C5 0.049(2) 0.034(2) 0.0164(18) -0.0041(15) -0.0014(16) -0.0119(17) C6 0.039(2) 0.0284(18) 0.0219(19) -0.0057(15) -0.0091(15) -0.0155(16) C7 0.0331(19) 0.0228(16) 0.0242(19) -0.0037(14) -0.0052(15) -0.0135(14) C8 0.0210(17) 0.0300(18) 0.0206(18) -0.0039(14) -0.0058(14) 0.0023(14) C9 0.0170(17) 0.041(2) 0.029(2) -0.0046(16) -0.0014(14) -0.0046(15) C10 0.0244(18) 0.0331(19) 0.0220(18) 0.0050(15) -0.0055(14) -0.0133(15) C11 0.033(2) 0.036(2) 0.045(3) -0.0112(19) -0.0075(18) 0.0036(17) C12 0.028(2) 0.050(2) 0.046(3) -0.002(2) -0.0047(18) -0.0211(18) C13 0.0199(16) 0.0197(15) 0.0233(18) -0.0025(13) -0.0030(13) -0.0074(13) C14 0.0371(19) 0.0169(15) 0.0203(18) 0.0000(13) -0.0045(15) -0.0069(14) C15 0.0297(18) 0.0247(16) 0.0175(17) -0.0078(14) 0.0030(14) -0.0143(14) C16 0.044(2) 0.0176(16) 0.030(2) -0.0032(15) -0.0060(17) 0.0025(15) C17 0.062(3) 0.0229(17) 0.0161(18) -0.0028(14) -0.0021(17) -0.0119(17) C18 0.0187(15) 0.0177(14) 0.0200(17) -0.0083(13) -0.0009(12) -0.0038(12) C19 0.050(6) 0.055(6) 0.053(7) -0.008(5) 0.001(5) -0.033(5) C23 0.069(10) 0.047(8) 0.045(8) 0.013(6) -0.004(6) -0.005(7) C24 0.035(6) 0.047(8) 0.050(8) 0.001(6) -0.001(5) -0.014(5) C25 0.028(6) 0.020(6) 0.032(8) -0.007(5) -0.010(5) -0.003(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 In1 O1 2.108(2) . ? In1 O3 2.156(2) . ? In1 O2 2.159(2) . ? In1 N2 2.203(3) . ? In1 N1 2.235(3) . ? In1 N3 2.241(3) . ? O1 C1 1.293(4) . ? N1 C3 1.305(4) . ? N1 C6 1.471(4) . ? C1 C2 1.366(5) . ? C1 C4 1.522(4) . ? C20 C25 1.419(7) . ? C20 C21 1.419(7) . ? C20 C19 1.495(7) . ? C21 C22 1.425(7) . ? C21 H21 0.9500 . ? C22 C23 1.431(8) . ? C22 H22 0.9500 . ? O2 C8 1.287(4) . ? N2 C10 1.306(4) . ? N2 C7 1.451(4) . ? C2 C3 1.426(5) . ? C2 H2A 0.9500 . ? O3 C13 1.279(4) . ? N3 C15 1.310(4) . ? N3 C18 1.474(4) . ? C3 C5 1.506(5) . ? 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 C7 1.524(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.379(5) . ? C8 C11 1.514(5) . ? C9 C10 1.424(5) . ? C9 H9A 0.9500 . ? C10 C12 1.503(5) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.370(5) . ? C13 C16 1.512(4) . ? C14 C15 1.429(5) . ? C14 H14A 0.9500 . ? C15 C17 1.514(5) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C18 1.525(6) 2_766 ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C23 C24 1.424(8) . ? C23 H23 0.9500 . ? C24 C25 1.424(7) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? 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 O1 In1 O3 99.89(9) . . ? O1 In1 O2 89.84(9) . . ? O3 In1 O2 169.37(8) . . ? O1 In1 N2 157.03(10) . . ? O3 In1 N2 90.58(9) . . ? O2 In1 N2 81.88(9) . . ? O1 In1 N1 85.77(9) . . ? O3 In1 N1 83.34(9) . . ? O2 In1 N1 101.79(10) . . ? N2 In1 N1 75.12(10) . . ? O1 In1 N3 94.20(9) . . ? O3 In1 N3 83.92(9) . . ? O2 In1 N3 91.15(9) . . ? N2 In1 N3 107.29(10) . . ? N1 In1 N3 167.07(9) . . ? C1 O1 In1 127.6(2) . . ? C3 N1 C6 119.6(3) . . ? C3 N1 In1 127.0(2) . . ? C6 N1 In1 113.2(2) . . ? O1 C1 C2 128.0(3) . . ? O1 C1 C4 112.7(3) . . ? C2 C1 C4 119.3(3) . . ? C25 C20 C21 117.1(8) . . ? C25 C20 C19 121.9(8) . . ? C21 C20 C19 121.0(10) . . ? C20 C21 C22 118.2(10) . . ? C20 C21 H21 120.9 . . ? C22 C21 H21 120.9 . . ? C21 C22 C23 125.9(11) . . ? C21 C22 H22 117.0 . . ? C23 C22 H22 117.0 . . ? C8 O2 In1 124.2(2) . . ? C10 N2 C7 123.9(3) . . ? C10 N2 In1 127.2(2) . . ? C7 N2 In1 107.9(2) . . ? C1 C2 C3 128.8(3) . . ? C1 C2 H2A 115.6 . . ? C3 C2 H2A 115.6 . . ? C13 O3 In1 128.2(2) . . ? C15 N3 C18 118.4(3) . . ? C15 N3 In1 125.8(2) . . ? C18 N3 In1 115.8(2) . . ? N1 C3 C2 122.6(3) . . ? N1 C3 C5 121.1(3) . . ? C2 C3 C5 116.3(3) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C7 110.7(3) . . ? N1 C6 H6A 109.5 . . ? C7 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? N2 C7 C6 107.8(3) . . ? N2 C7 H7A 110.1 . . ? C6 C7 H7A 110.1 . . ? N2 C7 H7B 110.1 . . ? C6 C7 H7B 110.1 . . ? H7A C7 H7B 108.5 . . ? O2 C8 C9 126.6(3) . . ? O2 C8 C11 113.9(3) . . ? C9 C8 C11 119.3(3) . . ? C8 C9 C10 125.5(3) . . ? C8 C9 H9A 117.3 . . ? C10 C9 H9A 117.3 . . ? N2 C10 C9 121.9(3) . . ? N2 C10 C12 122.1(3) . . ? C9 C10 C12 116.0(3) . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O3 C13 C14 126.5(3) . . ? O3 C13 C16 114.9(3) . . ? C14 C13 C16 118.6(3) . . ? C13 C14 C15 127.9(3) . . ? C13 C14 H14A 116.0 . . ? C15 C14 H14A 116.0 . . ? N3 C15 C14 124.4(3) . . ? N3 C15 C17 121.2(3) . . ? C14 C15 C17 114.5(3) . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N3 C18 C18 109.7(3) . 2_766 ? N3 C18 H18A 109.7 . . ? C18 C18 H18A 109.7 2_766 . ? N3 C18 H18B 109.7 . . ? C18 C18 H18B 109.7 2_766 . ? H18A C18 H18B 108.2 . . ? C24 C23 C22 114.4(11) . . ? C24 C23 H23 122.8 . . ? C22 C23 H23 122.8 . . ? C25 C24 C23 120.6(12) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C20 C25 C24 123.8(10) . . ? C20 C25 H25 118.1 . . ? C24 C25 H25 118.1 . . ? 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 O3 In1 O1 C1 86.1(3) . . . . ? O2 In1 O1 C1 -98.2(3) . . . . ? N2 In1 O1 C1 -29.8(4) . . . . ? N1 In1 O1 C1 3.7(3) . . . . ? N3 In1 O1 C1 170.7(3) . . . . ? O1 In1 N1 C3 -4.2(3) . . . . ? O3 In1 N1 C3 -104.7(3) . . . . ? O2 In1 N1 C3 84.8(3) . . . . ? N2 In1 N1 C3 163.0(3) . . . . ? N3 In1 N1 C3 -94.5(5) . . . . ? O1 In1 N1 C6 -178.9(2) . . . . ? O3 In1 N1 C6 80.6(2) . . . . ? O2 In1 N1 C6 -90.0(2) . . . . ? N2 In1 N1 C6 -11.8(2) . . . . ? N3 In1 N1 C6 90.7(5) . . . . ? In1 O1 C1 C2 -2.5(5) . . . . ? In1 O1 C1 C4 177.1(2) . . . . ? C25 C20 C21 C22 2.1(14) . . . . ? C19 C20 C21 C22 -179.3(10) . . . . ? C20 C21 C22 C23 -2.5(18) . . . . ? O1 In1 O2 C8 -167.2(3) . . . . ? O3 In1 O2 C8 -10.8(6) . . . . ? N2 In1 O2 C8 34.3(3) . . . . ? N1 In1 O2 C8 107.2(3) . . . . ? N3 In1 O2 C8 -73.0(3) . . . . ? O1 In1 N2 C10 -97.3(4) . . . . ? O3 In1 N2 C10 145.1(3) . . . . ? O2 In1 N2 C10 -27.4(3) . . . . ? N1 In1 N2 C10 -132.0(3) . . . . ? N3 In1 N2 C10 61.3(3) . . . . ? O1 In1 N2 C7 71.1(3) . . . . ? O3 In1 N2 C7 -46.5(2) . . . . ? O2 In1 N2 C7 141.0(2) . . . . ? N1 In1 N2 C7 36.4(2) . . . . ? N3 In1 N2 C7 -130.3(2) . . . . ? O1 C1 C2 C3 -0.1(6) . . . . ? C4 C1 C2 C3 -179.7(3) . . . . ? O1 In1 O3 C13 111.9(2) . . . . ? O2 In1 O3 C13 -44.1(6) . . . . ? N2 In1 O3 C13 -88.7(3) . . . . ? N1 In1 O3 C13 -163.6(3) . . . . ? N3 In1 O3 C13 18.7(2) . . . . ? O1 In1 N3 C15 -115.4(3) . . . . ? O3 In1 N3 C15 -15.8(3) . . . . ? O2 In1 N3 C15 154.7(3) . . . . ? N2 In1 N3 C15 72.9(3) . . . . ? N1 In1 N3 C15 -26.0(6) . . . . ? O1 In1 N3 C18 66.1(2) . . . . ? O3 In1 N3 C18 165.6(2) . . . . ? O2 In1 N3 C18 -23.8(2) . . . . ? N2 In1 N3 C18 -105.7(2) . . . . ? N1 In1 N3 C18 155.5(4) . . . . ? C6 N1 C3 C2 177.9(3) . . . . ? In1 N1 C3 C2 3.4(5) . . . . ? C6 N1 C3 C5 -2.8(5) . . . . ? In1 N1 C3 C5 -177.3(2) . . . . ? C1 C2 C3 N1 -0.5(6) . . . . ? C1 C2 C3 C5 -179.8(3) . . . . ? C3 N1 C6 C7 171.1(3) . . . . ? In1 N1 C6 C7 -13.7(4) . . . . ? C10 N2 C7 C6 113.7(4) . . . . ? In1 N2 C7 C6 -55.2(3) . . . . ? N1 C6 C7 N2 45.3(4) . . . . ? In1 O2 C8 C9 -23.2(5) . . . . ? In1 O2 C8 C11 160.9(2) . . . . ? O2 C8 C9 C10 -12.9(6) . . . . ? C11 C8 C9 C10 162.9(4) . . . . ? C7 N2 C10 C9 -159.0(3) . . . . ? In1 N2 C10 C9 7.6(5) . . . . ? C7 N2 C10 C12 18.3(5) . . . . ? In1 N2 C10 C12 -175.0(3) . . . . ? C8 C9 C10 N2 21.1(6) . . . . ? C8 C9 C10 C12 -156.5(4) . . . . ? In1 O3 C13 C14 -13.8(5) . . . . ? In1 O3 C13 C16 167.7(2) . . . . ? O3 C13 C14 C15 -3.0(6) . . . . ? C16 C13 C14 C15 175.5(3) . . . . ? C18 N3 C15 C14 -173.1(3) . . . . ? In1 N3 C15 C14 8.4(5) . . . . ? C18 N3 C15 C17 6.7(4) . . . . ? In1 N3 C15 C17 -171.8(2) . . . . ? C13 C14 C15 N3 5.4(6) . . . . ? C13 C14 C15 C17 -174.5(4) . . . . ? C15 N3 C18 C18 90.0(4) . . . 2_766 ? In1 N3 C18 C18 -91.3(3) . . . 2_766 ? C21 C22 C23 C24 2.1(19) . . . . ? C22 C23 C24 C25 -1(2) . . . . ? C21 C20 C25 C24 -1.7(15) . . . . ? C19 C20 C25 C24 179.7(12) . . . . ? C23 C24 C25 C20 1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.681 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.104 # Attachment '- 5rev.CIF' data_g:\nogrp1~1\revfil~1\ar287a _database_code_depnum_ccdc_archive 'CCDC 861505' #TrackingRef '- 5rev.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (((NO)InCl))2.PhMe _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H44 Cl2 In2 N4 O4' _chemical_formula_weight 837.24 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' Cl Cl 0.1484 0.1585 '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' O O 0.0106 0.0060 '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 9.4301(7) _cell_length_b 9.6908(9) _cell_length_c 11.2031(9) _cell_angle_alpha 90.674(7) _cell_angle_beta 110.084(7) _cell_angle_gamma 112.240(8) _cell_volume 878.10(13) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9849 _cell_measurement_theta_min 2.7464 _cell_measurement_theta_max 29.4643 _exptl_crystal_description CUBE _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 422 _exptl_absorpt_coefficient_mu 1.504 _exptl_absorpt_correction_T_min 0.53470 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Xcalibur, Atlas, Gemini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.3281 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5976 _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.31 _reflns_number_total 3427 _reflns_number_gt 3054 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material SHELXL-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. A highly disordered toluene molecule was refined using distant restraints. ; _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^)+(0.0828P)^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 3427 _refine_ls_number_parameters 213 _refine_ls_number_restraints 73 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1247 _refine_ls_wR_factor_gt 0.1187 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.545 _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 0.11297(5) -0.01188(5) 0.40448(4) 0.0188(2) Uani 1 1 d . . . Cl1 Cl 0.1404(2) -0.2203(2) 0.30374(19) 0.0312(4) Uani 1 1 d . . . O1 O -0.0469(7) 0.0109(6) 0.2304(5) 0.0285(11) Uani 1 1 d . . . O2 O 0.0386(6) 0.1526(5) 0.5007(5) 0.0216(10) Uani 1 1 d . . . N1 N 0.3158(7) 0.1829(7) 0.3898(6) 0.0250(13) Uani 1 1 d . . . N2 N 0.3081(7) 0.0321(7) 0.5965(6) 0.0233(12) Uani 1 1 d . . . C1 C -0.0022(10) 0.1075(10) 0.1584(8) 0.0303(16) Uani 1 1 d . . . C2 C 0.1556(11) 0.2171(10) 0.1825(8) 0.0342(18) Uani 1 1 d . . . H2 H 0.1651 0.2764 0.1165 0.041 Uiso 1 1 calc R . . C3 C 0.3055(10) 0.2536(8) 0.2916(8) 0.0283(16) Uani 1 1 d . . . C4 C -0.1396(12) 0.0935(12) 0.0356(9) 0.044(2) Uani 1 1 d . . . H4A H -0.1980 -0.0121 -0.0069 0.067 Uiso 1 1 calc R . . H4B H -0.0942 0.1567 -0.0212 0.067 Uiso 1 1 calc R . . H4C H -0.2169 0.1269 0.0543 0.067 Uiso 1 1 calc R . . C5 C 0.4541(12) 0.3823(10) 0.2872(10) 0.041(2) Uani 1 1 d . . . H5A H 0.4778 0.4725 0.3441 0.061 Uiso 1 1 calc R . . H5B H 0.4322 0.4032 0.1988 0.061 Uiso 1 1 calc R . . H5C H 0.5495 0.3555 0.3159 0.061 Uiso 1 1 calc R . . C6 C 0.4723(9) 0.2226(9) 0.4996(8) 0.0294(16) Uani 1 1 d . . . H6A H 0.5416 0.3319 0.5115 0.035 Uiso 1 1 calc R . . H6B H 0.5333 0.1660 0.4827 0.035 Uiso 1 1 calc R . . C7 C 0.4375(9) 0.1838(9) 0.6226(7) 0.0276(15) Uani 1 1 d . . . H7A H 0.5396 0.1895 0.6921 0.033 Uiso 1 1 calc R . . H7B H 0.4023 0.2577 0.6518 0.033 Uiso 1 1 calc R . . C10 C 0.3155(9) -0.0685(8) 0.6722(7) 0.0251(15) Uani 1 1 d . . . C12 C 0.4648(11) -0.0410(10) 0.7918(9) 0.0367(18) Uani 1 1 d . . . H12A H 0.5632 -0.0102 0.7697 0.055 Uiso 1 1 calc R . . H12B H 0.4499 -0.1340 0.8291 0.055 Uiso 1 1 calc R . . H12C H 0.4788 0.0392 0.8545 0.055 Uiso 1 1 calc R . . C8 C -0.0176(9) 0.2494(8) 0.4362(7) 0.0237(14) Uani 1 1 d . . . C11 C 0.1141(10) 0.4052(8) 0.4576(9) 0.0323(17) Uani 1 1 d . . . H11A H 0.1588 0.4499 0.5486 0.048 Uiso 1 1 calc R . . H11B H 0.0666 0.4679 0.4041 0.048 Uiso 1 1 calc R . . H11C H 0.2030 0.3995 0.4342 0.048 Uiso 1 1 calc R . . C9 C -0.1772(9) 0.2138(8) 0.3573(7) 0.0259(15) Uani 1 1 d . . . H9 H -0.2004 0.2929 0.3173 0.031 Uiso 1 1 calc R . . C18 C 0.661(3) 0.5989(18) 1.0697(17) 0.107(16) Uani 0.50 1 d PDU A -1 H18 H 0.7701 0.6723 1.1166 0.129 Uiso 0.50 1 calc PR A -1 C19 C 0.528(3) 0.6216(18) 1.0418(17) 0.093(12) Uani 0.50 1 d PRDU A -1 H19 H 0.5440 0.7209 1.0708 0.111 Uiso 0.50 1 calc PR A -1 C17 C 0.624(3) 0.4599(18) 1.0235(17) 0.089(13) Uani 0.50 1 d PRDU A -1 H17 H 0.7166 0.4345 1.0464 0.107 Uiso 0.50 1 calc PR A -1 C13 C 0.223(3) 0.5650(18) 0.9576(17) 0.117(14) Uani 0.50 1 d PRDU A -1 H13A H 0.2147 0.5798 1.0414 0.175 Uiso 0.50 1 calc PR A -1 H13B H 0.1185 0.4863 0.8982 0.175 Uiso 0.50 1 calc PR A -1 H13C H 0.2440 0.6598 0.9227 0.175 Uiso 0.50 1 calc PR A -1 C14 C 0.357(3) 0.5188(18) 0.9733(17) 0.097(14) Uani 0.50 1 d PRDU A -1 C15 C 0.321(3) 0.3682(18) 0.9159(17) 0.088(11) Uani 0.50 1 d PRDU A -1 H15 H 0.2123 0.2971 0.8651 0.105 Uiso 0.50 1 calc PR A -1 C16 C 0.471(3) 0.3365(18) 0.9448(17) 0.080(10) Uani 0.50 1 d PRDU A -1 H16 H 0.4659 0.2426 0.9139 0.096 Uiso 0.50 1 calc PR A -1 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 0.0106(3) 0.0204(3) 0.0236(3) 0.00836(19) 0.0051(2) 0.0053(2) Cl1 0.0293(10) 0.0311(9) 0.0354(10) 0.0051(8) 0.0109(8) 0.0157(8) O1 0.024(3) 0.034(3) 0.027(3) 0.010(2) 0.007(2) 0.013(2) O2 0.017(2) 0.019(2) 0.029(3) 0.008(2) 0.009(2) 0.0085(19) N1 0.017(3) 0.024(3) 0.034(3) 0.009(3) 0.011(3) 0.007(2) N2 0.017(3) 0.024(3) 0.028(3) 0.007(2) 0.007(2) 0.008(2) C1 0.029(4) 0.039(4) 0.028(4) 0.009(3) 0.012(3) 0.018(3) C2 0.036(4) 0.039(5) 0.031(4) 0.018(4) 0.015(4) 0.016(4) C3 0.033(4) 0.021(3) 0.039(4) 0.010(3) 0.021(4) 0.012(3) C4 0.039(5) 0.060(6) 0.037(5) 0.018(4) 0.010(4) 0.025(5) C5 0.039(5) 0.037(5) 0.046(5) 0.020(4) 0.022(4) 0.009(4) C6 0.016(3) 0.032(4) 0.037(4) 0.008(3) 0.010(3) 0.006(3) C7 0.018(3) 0.029(4) 0.027(4) 0.003(3) 0.004(3) 0.005(3) C10 0.021(4) 0.023(3) 0.031(4) 0.005(3) 0.010(3) 0.010(3) C12 0.032(4) 0.038(5) 0.036(4) 0.011(4) 0.006(4) 0.016(4) C8 0.024(4) 0.017(3) 0.033(4) 0.010(3) 0.014(3) 0.010(3) C11 0.024(4) 0.021(4) 0.052(5) 0.009(3) 0.016(4) 0.009(3) C9 0.026(4) 0.024(4) 0.034(4) 0.014(3) 0.012(3) 0.015(3) C18 0.12(2) 0.075(18) 0.032(12) -0.016(12) 0.038(14) -0.070(19) C19 0.18(3) 0.021(10) 0.053(14) -0.002(9) 0.080(18) -0.016(15) C17 0.057(16) 0.15(3) 0.059(19) 0.05(2) 0.042(14) 0.028(19) C13 0.16(4) 0.17(3) 0.11(3) 0.10(3) 0.08(3) 0.13(3) C14 0.17(3) 0.056(16) 0.09(3) 0.034(16) 0.08(2) 0.04(2) C15 0.093(14) 0.087(14) 0.088(14) 0.019(9) 0.041(9) 0.035(10) C16 0.089(12) 0.073(13) 0.073(13) 0.012(9) 0.032(9) 0.028(9) _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 O1 2.090(5) . ? In1 O2 2.153(5) 2_556 ? In1 N1 2.177(6) . ? In1 N2 2.205(6) . ? In1 O2 2.349(5) . ? In1 Cl1 2.4421(19) . ? O1 C1 1.287(10) . ? O2 C8 1.346(9) . ? O2 In1 2.153(5) 2_556 ? N1 C3 1.298(10) . ? N1 C6 1.466(10) . ? N2 C10 1.306(10) . ? N2 C7 1.457(9) . ? C1 C2 1.391(12) . ? C1 C4 1.493(12) . ? C2 C3 1.429(12) . ? C2 H2 0.9500 . ? C3 C5 1.500(11) . ? 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 C7 1.542(11) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C10 C9 1.448(10) 2_556 ? C10 C12 1.503(11) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C8 C9 1.361(11) . ? C8 C11 1.499(10) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C9 C10 1.448(10) 2_556 ? C9 H9 0.9500 . ? C18 C19 1.2945 . ? C18 C17 1.3065 . ? C18 H18 0.9500 . ? C19 C14 1.4431 . ? C19 H19 0.9500 . ? C17 C16 1.4446 . ? C17 H17 0.9500 . ? C13 C14 1.4579 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.4521 . ? C15 C16 1.4863 . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 O1 In1 O2 107.1(2) . 2_556 ? O1 In1 N1 89.9(2) . . ? O2 In1 N1 156.0(2) 2_556 . ? O1 In1 N2 164.3(2) . . ? O2 In1 N2 81.9(2) 2_556 . ? N1 In1 N2 78.1(2) . . ? O1 In1 O2 85.4(2) . . ? O2 In1 O2 75.63(19) 2_556 . ? N1 In1 O2 89.2(2) . . ? N2 In1 O2 84.4(2) . . ? O1 In1 Cl1 92.96(16) . . ? O2 In1 Cl1 94.52(14) 2_556 . ? N1 In1 Cl1 101.69(17) . . ? N2 In1 Cl1 99.28(16) . . ? O2 In1 Cl1 168.97(13) . . ? C1 O1 In1 124.7(5) . . ? C8 O2 In1 115.3(4) . 2_556 ? C8 O2 In1 122.1(4) . . ? In1 O2 In1 104.37(19) 2_556 . ? C3 N1 C6 122.0(6) . . ? C3 N1 In1 124.6(5) . . ? C6 N1 In1 113.3(5) . . ? C10 N2 C7 123.9(6) . . ? C10 N2 In1 124.7(5) . . ? C7 N2 In1 111.1(5) . . ? O1 C1 C2 127.4(8) . . ? O1 C1 C4 113.7(7) . . ? C2 C1 C4 119.0(8) . . ? C1 C2 C3 129.7(8) . . ? C1 C2 H2 115.2 . . ? C3 C2 H2 115.2 . . ? N1 C3 C2 123.5(7) . . ? N1 C3 C5 120.9(8) . . ? C2 C3 C5 115.6(7) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C7 109.8(6) . . ? N1 C6 H6A 109.7 . . ? C7 C6 H6A 109.7 . . ? N1 C6 H6B 109.7 . . ? C7 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? N2 C7 C6 109.8(6) . . ? N2 C7 H7A 109.7 . . ? C6 C7 H7A 109.7 . . ? N2 C7 H7B 109.7 . . ? C6 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? N2 C10 C9 120.4(7) . 2_556 ? N2 C10 C12 122.6(7) . . ? C9 C10 C12 117.1(7) 2_556 . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O2 C8 C9 125.0(6) . . ? O2 C8 C11 113.6(6) . . ? C9 C8 C11 121.4(7) . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C9 C10 127.0(7) . 2_556 ? C8 C9 H9 116.5 . . ? C10 C9 H9 116.5 2_556 . ? C19 C18 C17 109.6 . . ? C19 C18 H18 125.2 . . ? C17 C18 H18 125.2 . . ? C18 C19 C14 129.9 . . ? C18 C19 H19 115.1 . . ? C14 C19 H19 115.1 . . ? C18 C17 C16 133.4 . . ? C18 C17 H17 113.3 . . ? C16 C17 H17 113.3 . . ? C19 C14 C15 119.1 . . ? C19 C14 C13 121.3 . . ? C15 C14 C13 119.6 . . ? C14 C15 C16 113.1 . . ? C14 C15 H15 123.5 . . ? C16 C15 H15 123.5 . . ? C17 C16 C15 114.7 . . ? C17 C16 H16 122.6 . . ? C15 C16 H16 122.6 . . ? 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 O2 In1 O1 C1 167.2(6) 2_556 . . . ? N1 In1 O1 C1 4.5(6) . . . . ? N2 In1 O1 C1 44.0(11) . . . . ? O2 In1 O1 C1 93.8(6) . . . . ? Cl1 In1 O1 C1 -97.2(6) . . . . ? O1 In1 O2 C8 -24.1(5) . . . . ? O2 In1 O2 C8 -133.0(6) 2_556 . . . ? N1 In1 O2 C8 65.8(5) . . . . ? N2 In1 O2 C8 143.9(5) . . . . ? Cl1 In1 O2 C8 -105.7(8) . . . . ? O1 In1 O2 In1 108.9(2) . . . 2_556 ? O2 In1 O2 In1 0.0 2_556 . . 2_556 ? N1 In1 O2 In1 -161.1(3) . . . 2_556 ? N2 In1 O2 In1 -83.0(2) . . . 2_556 ? Cl1 In1 O2 In1 27.3(8) . . . 2_556 ? O1 In1 N1 C3 -5.2(6) . . . . ? O2 In1 N1 C3 -140.8(6) 2_556 . . . ? N2 In1 N1 C3 -175.0(6) . . . . ? O2 In1 N1 C3 -90.5(6) . . . . ? Cl1 In1 N1 C3 87.8(6) . . . . ? O1 In1 N1 C6 178.6(5) . . . . ? O2 In1 N1 C6 43.0(8) 2_556 . . . ? N2 In1 N1 C6 8.8(5) . . . . ? O2 In1 N1 C6 93.3(5) . . . . ? Cl1 In1 N1 C6 -88.4(5) . . . . ? O1 In1 N2 C10 162.8(7) . . . . ? O2 In1 N2 C10 36.8(6) 2_556 . . . ? N1 In1 N2 C10 -156.6(6) . . . . ? O2 In1 N2 C10 113.0(6) . . . . ? Cl1 In1 N2 C10 -56.5(6) . . . . ? O1 In1 N2 C7 -23.1(10) . . . . ? O2 In1 N2 C7 -149.2(5) 2_556 . . . ? N1 In1 N2 C7 17.5(5) . . . . ? O2 In1 N2 C7 -72.9(5) . . . . ? Cl1 In1 N2 C7 117.6(4) . . . . ? In1 O1 C1 C2 -2.3(12) . . . . ? In1 O1 C1 C4 176.6(5) . . . . ? O1 C1 C2 C3 -1.7(15) . . . . ? C4 C1 C2 C3 179.4(9) . . . . ? C6 N1 C3 C2 179.4(7) . . . . ? In1 N1 C3 C2 3.5(11) . . . . ? C6 N1 C3 C5 -1.1(11) . . . . ? In1 N1 C3 C5 -177.0(6) . . . . ? C1 C2 C3 N1 1.0(14) . . . . ? C1 C2 C3 C5 -178.6(9) . . . . ? C3 N1 C6 C7 151.7(7) . . . . ? In1 N1 C6 C7 -32.0(7) . . . . ? C10 N2 C7 C6 134.6(7) . . . . ? In1 N2 C7 C6 -39.5(7) . . . . ? N1 C6 C7 N2 47.2(8) . . . . ? C7 N2 C10 C9 176.5(7) . . . 2_556 ? In1 N2 C10 C9 -10.2(10) . . . 2_556 ? C7 N2 C10 C12 -3.9(11) . . . . ? In1 N2 C10 C12 169.4(6) . . . . ? In1 O2 C8 C9 -44.6(9) 2_556 . . . ? In1 O2 C8 C9 83.8(8) . . . . ? In1 O2 C8 C11 135.9(5) 2_556 . . . ? In1 O2 C8 C11 -95.7(7) . . . . ? O2 C8 C9 C10 0.2(13) . . . 2_556 ? C11 C8 C9 C10 179.6(7) . . . 2_556 ? C17 C18 C19 C14 1.0 . . . . ? C19 C18 C17 C16 4.3 . . . . ? C18 C19 C14 C15 -5.1 . . . . ? C18 C19 C14 C13 176.7 . . . . ? C19 C14 C15 C16 4.0 . . . . ? C13 C14 C15 C16 -177.8 . . . . ? C18 C17 C16 C15 -4.7 . . . . ? C14 C15 C16 C17 -0.1 . . . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 26.31 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 1.675 _refine_diff_density_min -0.996 _refine_diff_density_rms 0.162 # Attachment '- 6 rev.CIF' data_f:\ltuxra~1\ar285n~1\ar285 _database_code_depnum_ccdc_archive 'CCDC 861506' #TrackingRef '- 6 rev.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ((NO)InCl(thf)) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H26 Cl In N2 O3' _chemical_formula_weight 444.66 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 8.0463(14) _cell_length_b 14.8894(7) _cell_length_c 15.5567(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.294(8) _cell_angle_gamma 90.00 _cell_volume 1860.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 12119 _cell_measurement_theta_min 2.7782 _cell_measurement_theta_max 29.4335 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 1.428 _exptl_absorpt_correction_T_min 0.92555 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Xcalibur, Atlas, Gemini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24793 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 29.52 _reflns_number_total 4740 _reflns_number_gt 3970 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material SHELXL-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^)+(0.0398P)^2^+3.8516P] 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 4740 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.56803(3) 0.980601(15) 0.233575(13) 0.02569(8) Uani 1 1 d . . . Cl1 Cl 0.81934(11) 1.00607(6) 0.15515(6) 0.03655(19) Uani 1 1 d . . . O1 O 0.5771(3) 1.10078(18) 0.30381(17) 0.0420(6) Uani 1 1 d . . . O2 O 0.6778(3) 0.89491(17) 0.32777(15) 0.0351(5) Uani 1 1 d . . . O3 O 0.3411(3) 0.9483(3) 0.32483(16) 0.0566(9) Uani 1 1 d . . . N1 N 0.3783(3) 1.03907(19) 0.14480(17) 0.0286(6) Uani 1 1 d . . . N2 N 0.4858(3) 0.86390(19) 0.15937(16) 0.0273(6) Uani 1 1 d . . . C1 C 0.4864(5) 1.1705(3) 0.2861(2) 0.0368(8) Uani 1 1 d . . . C2 C 0.3739(5) 1.1820(2) 0.2167(2) 0.0380(8) Uani 1 1 d . . . H2A H 0.3256 1.2401 0.2119 0.046 Uiso 1 1 calc R . . C3 C 0.3187(4) 1.1200(2) 0.1511(2) 0.0314(7) Uani 1 1 d . . . C4 C 0.5110(6) 1.2455(3) 0.3510(3) 0.0483(10) Uani 1 1 d . . . H4A H 0.5934 1.2271 0.3965 0.072 Uiso 1 1 calc R . . H4B H 0.4050 1.2586 0.3765 0.072 Uiso 1 1 calc R . . H4C H 0.5505 1.2993 0.3223 0.072 Uiso 1 1 calc R . . C5 C 0.1804(5) 1.1519(3) 0.0884(3) 0.0437(9) Uani 1 1 d . . . H5A H 0.1532 1.1044 0.0463 0.066 Uiso 1 1 calc R . . H5B H 0.2168 1.2057 0.0585 0.066 Uiso 1 1 calc R . . H5C H 0.0817 1.1661 0.1199 0.066 Uiso 1 1 calc R . . C6 C 0.3002(4) 0.9737(2) 0.0848(2) 0.0324(7) Uani 1 1 d . . . H6A H 0.2784 1.0024 0.0278 0.039 Uiso 1 1 calc R . . H6B H 0.1921 0.9545 0.1060 0.039 Uiso 1 1 calc R . . C7 C 0.4113(4) 0.8917(2) 0.0752(2) 0.0333(7) Uani 1 1 d . . . H7A H 0.3445 0.8417 0.0493 0.040 Uiso 1 1 calc R . . H7B H 0.5005 0.9062 0.0362 0.040 Uiso 1 1 calc R . . C8 C 0.6689(4) 0.8081(2) 0.3245(2) 0.0292(7) Uani 1 1 d . . . C9 C 0.6014(4) 0.7555(2) 0.2592(2) 0.0315(7) Uani 1 1 d . . . H9A H 0.6076 0.6926 0.2692 0.038 Uiso 1 1 calc R . . C10 C 0.5231(4) 0.7814(2) 0.1783(2) 0.0284(6) Uani 1 1 d . . . C11 C 0.7464(5) 0.7620(3) 0.4031(2) 0.0400(8) Uani 1 1 d . . . H11A H 0.7903 0.8072 0.4442 0.060 Uiso 1 1 calc R . . H11B H 0.8372 0.7230 0.3863 0.060 Uiso 1 1 calc R . . H11C H 0.6620 0.7257 0.4300 0.060 Uiso 1 1 calc R . . C12 C 0.4865(6) 0.7057(3) 0.1152(3) 0.0479(10) Uani 1 1 d . . . H12A H 0.4339 0.7300 0.0618 0.072 Uiso 1 1 calc R . . H12B H 0.4111 0.6625 0.1403 0.072 Uiso 1 1 calc R . . H12C H 0.5906 0.6755 0.1027 0.072 Uiso 1 1 calc R . . C13 C 0.1689(5) 0.9592(3) 0.3065(3) 0.0441(9) Uani 1 1 d . . . H13A H 0.1274 0.9164 0.2616 0.053 Uiso 1 1 calc R . . H13B H 0.1431 1.0211 0.2868 0.053 Uiso 1 1 calc R . . C14 C 0.0929(6) 0.9403(4) 0.3905(3) 0.0679(14) Uani 1 1 d . . . H14A H -0.0112 0.9749 0.3953 0.081 Uiso 1 1 calc R . . H14B H 0.0682 0.8755 0.3964 0.081 Uiso 1 1 calc R . . C15 C 0.2201(7) 0.9690(5) 0.4557(3) 0.0806(19) Uani 1 1 d . . . H15A H 0.2062 1.0333 0.4699 0.097 Uiso 1 1 calc R . . H15B H 0.2138 0.9331 0.5089 0.097 Uiso 1 1 calc R . . C16 C 0.3770(6) 0.9541(5) 0.4169(3) 0.0784(19) Uani 1 1 d . . . H16A H 0.4545 1.0044 0.4307 0.094 Uiso 1 1 calc R . . H16B H 0.4289 0.8977 0.4388 0.094 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 0.02634(13) 0.02919(13) 0.02076(12) -0.00021(8) -0.00545(8) -0.00191(8) Cl1 0.0305(4) 0.0444(5) 0.0349(4) 0.0028(3) 0.0022(3) -0.0035(3) O1 0.0437(15) 0.0414(15) 0.0397(14) -0.0132(11) -0.0071(12) 0.0065(12) O2 0.0400(13) 0.0373(13) 0.0264(11) 0.0047(10) -0.0131(10) -0.0050(11) O3 0.0322(14) 0.115(3) 0.0220(12) -0.0042(15) 0.0002(10) -0.0050(16) N1 0.0271(13) 0.0339(15) 0.0245(13) 0.0022(11) -0.0016(11) 0.0007(11) N2 0.0295(13) 0.0323(14) 0.0192(12) 0.0015(10) -0.0071(10) -0.0057(11) C1 0.0350(18) 0.0381(19) 0.0382(18) -0.0065(15) 0.0102(15) -0.0018(15) C2 0.0384(19) 0.0294(17) 0.047(2) 0.0009(15) 0.0110(16) 0.0028(14) C3 0.0259(16) 0.0374(18) 0.0316(16) 0.0101(14) 0.0065(13) 0.0025(13) C4 0.054(2) 0.041(2) 0.050(2) -0.0158(18) 0.0077(19) -0.0016(18) C5 0.0367(19) 0.049(2) 0.045(2) 0.0130(18) -0.0024(17) 0.0087(17) C6 0.0300(16) 0.042(2) 0.0238(15) 0.0064(13) -0.0076(13) -0.0021(14) C7 0.0402(19) 0.0413(19) 0.0174(14) -0.0007(13) -0.0085(13) -0.0031(15) C8 0.0254(15) 0.0353(17) 0.0264(15) 0.0095(13) -0.0013(12) -0.0024(13) C9 0.0336(17) 0.0294(17) 0.0307(16) 0.0058(13) -0.0042(13) 0.0003(13) C10 0.0267(15) 0.0318(17) 0.0265(15) 0.0002(13) -0.0017(12) -0.0041(12) C11 0.042(2) 0.046(2) 0.0305(17) 0.0139(15) -0.0102(15) -0.0045(16) C12 0.061(3) 0.037(2) 0.044(2) -0.0100(17) -0.0147(19) 0.0058(18) C13 0.0291(18) 0.064(3) 0.039(2) -0.0058(18) 0.0006(15) -0.0049(17) C14 0.043(2) 0.097(4) 0.065(3) 0.007(3) 0.019(2) -0.019(3) C15 0.068(3) 0.139(6) 0.036(2) -0.002(3) 0.015(2) -0.009(3) C16 0.046(3) 0.166(6) 0.0230(19) -0.002(3) 0.0016(18) -0.014(3) _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 O1 2.096(3) . ? In1 O2 2.099(2) . ? In1 N2 2.168(3) . ? In1 N1 2.180(3) . ? In1 O3 2.425(3) . ? In1 Cl1 2.4505(9) . ? O1 C1 1.290(5) . ? O2 C8 1.296(4) . ? O3 C13 1.408(5) . ? O3 C16 1.447(5) . ? N1 C3 1.303(4) . ? N1 C6 1.465(4) . ? N2 C10 1.294(4) . ? N2 C7 1.468(4) . ? C1 C2 1.378(6) . ? C1 C4 1.511(5) . ? C2 C3 1.428(5) . ? C2 H2A 0.9500 . ? C3 C5 1.513(5) . ? 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 C7 1.526(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.370(5) . ? C8 C11 1.506(4) . ? C9 C10 1.429(4) . ? C9 H9A 0.9500 . ? C10 C12 1.512(5) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.501(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.462(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.447(7) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? 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 O1 In1 O2 98.88(10) . . ? O1 In1 N2 164.21(11) . . ? O2 In1 N2 89.30(9) . . ? O1 In1 N1 89.52(10) . . ? O2 In1 N1 159.40(10) . . ? N2 In1 N1 78.56(10) . . ? O1 In1 O3 82.47(12) . . ? O2 In1 O3 76.80(11) . . ? N2 In1 O3 86.33(11) . . ? N1 In1 O3 85.79(10) . . ? O1 In1 Cl1 97.02(8) . . ? O2 In1 Cl1 96.63(7) . . ? N2 In1 Cl1 95.40(7) . . ? N1 In1 Cl1 100.99(8) . . ? O3 In1 Cl1 173.21(7) . . ? C1 O1 In1 125.0(2) . . ? C8 O2 In1 124.0(2) . . ? C13 O3 C16 109.4(3) . . ? C13 O3 In1 128.6(2) . . ? C16 O3 In1 117.0(2) . . ? C3 N1 C6 121.1(3) . . ? C3 N1 In1 124.7(2) . . ? C6 N1 In1 113.4(2) . . ? C10 N2 C7 123.2(3) . . ? C10 N2 In1 125.5(2) . . ? C7 N2 In1 110.2(2) . . ? O1 C1 C2 127.2(3) . . ? O1 C1 C4 113.6(3) . . ? C2 C1 C4 119.1(3) . . ? C1 C2 C3 130.0(3) . . ? C1 C2 H2A 115.0 . . ? C3 C2 H2A 115.0 . . ? N1 C3 C2 123.4(3) . . ? N1 C3 C5 120.1(3) . . ? C2 C3 C5 116.5(3) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C7 111.2(3) . . ? N1 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N1 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N2 C7 C6 110.5(3) . . ? N2 C7 H7A 109.6 . . ? C6 C7 H7A 109.6 . . ? N2 C7 H7B 109.6 . . ? C6 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? O2 C8 C9 128.1(3) . . ? O2 C8 C11 113.8(3) . . ? C9 C8 C11 118.0(3) . . ? C8 C9 C10 129.5(3) . . ? C8 C9 H9A 115.3 . . ? C10 C9 H9A 115.3 . . ? N2 C10 C9 122.7(3) . . ? N2 C10 C12 121.8(3) . . ? C9 C10 C12 115.5(3) . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O3 C13 C14 104.3(3) . . ? O3 C13 H13A 110.9 . . ? C14 C13 H13A 110.9 . . ? O3 C13 H13B 110.9 . . ? C14 C13 H13B 110.9 . . ? H13A C13 H13B 108.9 . . ? C15 C14 C13 104.1(4) . . ? C15 C14 H14A 110.9 . . ? C13 C14 H14A 110.9 . . ? C15 C14 H14B 110.9 . . ? C13 C14 H14B 110.9 . . ? H14A C14 H14B 108.9 . . ? C16 C15 C14 105.0(4) . . ? C16 C15 H15A 110.7 . . ? C14 C15 H15A 110.7 . . ? C16 C15 H15B 110.7 . . ? C14 C15 H15B 110.7 . . ? H15A C15 H15B 108.8 . . ? O3 C16 C15 107.0(4) . . ? O3 C16 H16A 110.3 . . ? C15 C16 H16A 110.3 . . ? O3 C16 H16B 110.3 . . ? C15 C16 H16B 110.3 . . ? H16A C16 H16B 108.6 . . ? 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 O2 In1 O1 C1 -159.9(3) . . . . ? N2 In1 O1 C1 -39.5(6) . . . . ? N1 In1 O1 C1 1.2(3) . . . . ? O3 In1 O1 C1 -84.6(3) . . . . ? Cl1 In1 O1 C1 102.2(3) . . . . ? O1 In1 O2 C8 163.7(3) . . . . ? N2 In1 O2 C8 -2.7(3) . . . . ? N1 In1 O2 C8 50.6(4) . . . . ? O3 In1 O2 C8 83.6(3) . . . . ? Cl1 In1 O2 C8 -98.1(3) . . . . ? O1 In1 O3 C13 96.9(4) . . . . ? O2 In1 O3 C13 -162.1(4) . . . . ? N2 In1 O3 C13 -71.9(4) . . . . ? N1 In1 O3 C13 6.9(4) . . . . ? Cl1 In1 O3 C13 -176.9(6) . . . . ? O1 In1 O3 C16 -55.0(4) . . . . ? O2 In1 O3 C16 46.0(4) . . . . ? N2 In1 O3 C16 136.1(4) . . . . ? N1 In1 O3 C16 -145.1(4) . . . . ? Cl1 In1 O3 C16 31.1(10) . . . . ? O1 In1 N1 C3 -0.3(3) . . . . ? O2 In1 N1 C3 114.3(3) . . . . ? N2 In1 N1 C3 169.3(3) . . . . ? O3 In1 N1 C3 82.2(3) . . . . ? Cl1 In1 N1 C3 -97.4(3) . . . . ? O1 In1 N1 C6 -170.0(2) . . . . ? O2 In1 N1 C6 -55.4(4) . . . . ? N2 In1 N1 C6 -0.4(2) . . . . ? O3 In1 N1 C6 -87.5(2) . . . . ? Cl1 In1 N1 C6 92.9(2) . . . . ? O1 In1 N2 C10 -126.9(4) . . . . ? O2 In1 N2 C10 -5.3(3) . . . . ? N1 In1 N2 C10 -168.6(3) . . . . ? O3 In1 N2 C10 -82.1(3) . . . . ? Cl1 In1 N2 C10 91.3(3) . . . . ? O1 In1 N2 C7 65.0(5) . . . . ? O2 In1 N2 C7 -173.4(2) . . . . ? N1 In1 N2 C7 23.4(2) . . . . ? O3 In1 N2 C7 109.8(2) . . . . ? Cl1 In1 N2 C7 -76.8(2) . . . . ? In1 O1 C1 C2 -3.5(5) . . . . ? In1 O1 C1 C4 176.1(2) . . . . ? O1 C1 C2 C3 5.2(6) . . . . ? C4 C1 C2 C3 -174.5(4) . . . . ? C6 N1 C3 C2 170.5(3) . . . . ? In1 N1 C3 C2 1.5(5) . . . . ? C6 N1 C3 C5 -7.7(5) . . . . ? In1 N1 C3 C5 -176.7(2) . . . . ? C1 C2 C3 N1 -3.9(6) . . . . ? C1 C2 C3 C5 174.3(4) . . . . ? C3 N1 C6 C7 168.1(3) . . . . ? In1 N1 C6 C7 -21.8(3) . . . . ? C10 N2 C7 C6 149.5(3) . . . . ? In1 N2 C7 C6 -42.1(3) . . . . ? N1 C6 C7 N2 42.2(4) . . . . ? In1 O2 C8 C9 5.6(5) . . . . ? In1 O2 C8 C11 -175.5(2) . . . . ? O2 C8 C9 C10 -0.3(6) . . . . ? C11 C8 C9 C10 -179.1(3) . . . . ? C7 N2 C10 C9 177.6(3) . . . . ? In1 N2 C10 C9 11.0(5) . . . . ? C7 N2 C10 C12 -2.3(5) . . . . ? In1 N2 C10 C12 -168.9(3) . . . . ? C8 C9 C10 N2 -9.1(6) . . . . ? C8 C9 C10 C12 170.8(4) . . . . ? C16 O3 C13 C14 -19.0(6) . . . . ? In1 O3 C13 C14 -172.6(3) . . . . ? O3 C13 C14 C15 30.6(6) . . . . ? C13 C14 C15 C16 -30.6(7) . . . . ? C13 O3 C16 C15 0.1(7) . . . . ? In1 O3 C16 C15 157.2(4) . . . . ? C14 C15 C16 O3 19.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.883 _refine_diff_density_min -0.949 _refine_diff_density_rms 0.107