# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 #TrackingRef '14732_web_deposit_cif_file_0_JingyuLiu_1350442429.2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H30 Al2 N2 O2' _chemical_formula_weight 504.52 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' Al Al 0.0645 0.0514 '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 orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 10.4697(7) _cell_length_b 18.1726(12) _cell_length_c 14.8982(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2834.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9619 _exptl_absorpt_correction_T_max 0.9832 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14713 _diffrn_reflns_av_R_equivalents 0.0620 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 26.04 _reflns_number_total 2797 _reflns_number_gt 1936 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0622P)^2^+0.8108P] 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 2797 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 Al1 Al -0.04512(6) 0.11841(3) 0.15147(5) 0.0349(2) Uani 1 1 d . . . O1 O 0.08471(14) 0.17322(8) 0.11567(11) 0.0387(4) Uani 1 1 d . . . N1 N 0.04999(17) 0.02515(9) 0.14393(12) 0.0336(4) Uani 1 1 d . . . C2 C -0.0836(3) 0.13343(16) 0.27780(17) 0.0544(7) Uani 1 1 d . . . H2A H -0.1306 0.1784 0.2850 0.082 Uiso 1 1 calc R . . H2B H -0.0053 0.1363 0.3112 0.082 Uiso 1 1 calc R . . H2C H -0.1337 0.0930 0.2996 0.082 Uiso 1 1 calc R . . C1 C -0.1813(2) 0.12428(14) 0.06244(18) 0.0547(7) Uani 1 1 d . . . H1A H -0.2254 0.1703 0.0687 0.082 Uiso 1 1 calc R . . H1B H -0.2403 0.0845 0.0715 0.082 Uiso 1 1 calc R . . H1C H -0.1454 0.1209 0.0033 0.082 Uiso 1 1 calc R . . C10 C -0.0032(2) -0.04239(11) 0.17775(15) 0.0366(5) Uani 1 1 d . . . C11 C 0.0643(2) -0.08648(13) 0.23647(18) 0.0456(6) Uani 1 1 d . . . H11A H 0.1445 -0.0719 0.2565 0.055 Uiso 1 1 calc R . . C6 C 0.4359(2) 0.12053(12) 0.00750(17) 0.0403(6) Uani 1 1 d . . . H6A H 0.5159 0.1094 -0.0160 0.048 Uiso 1 1 calc R . . C3 C 0.19585(19) 0.15588(11) 0.07927(14) 0.0317(5) Uani 1 1 d . . . C15 C -0.1256(2) -0.06277(13) 0.15198(17) 0.0461(6) Uani 1 1 d . . . H15A H -0.1735 -0.0321 0.1150 0.055 Uiso 1 1 calc R . . C9 C 0.1670(2) 0.02258(11) 0.11444(15) 0.0360(5) Uani 1 1 d . . . H9A H 0.2072 -0.0230 0.1168 0.043 Uiso 1 1 calc R . . C5 C 0.3908(2) 0.19258(12) 0.00643(15) 0.0369(5) Uani 1 1 d . . . H5A H 0.4415 0.2293 -0.0186 0.044 Uiso 1 1 calc R . . C4 C 0.2731(2) 0.21122(10) 0.04142(13) 0.0310(5) Uani 1 1 d . . . C7 C 0.3612(2) 0.06618(12) 0.04347(15) 0.0393(6) Uani 1 1 d . . . H7A H 0.3910 0.0180 0.0443 0.047 Uiso 1 1 calc R . . C14 C -0.1761(3) -0.12896(14) 0.18152(18) 0.0523(7) Uani 1 1 d . . . H14A H -0.2574 -0.1431 0.1631 0.063 Uiso 1 1 calc R . . C13 C -0.1071(3) -0.17390(13) 0.23783(17) 0.0497(7) Uani 1 1 d . . . H13A H -0.1412 -0.2185 0.2570 0.060 Uiso 1 1 calc R . . C12 C 0.0121(3) -0.15260(13) 0.26549(18) 0.0504(7) Uani 1 1 d . . . H12A H 0.0585 -0.1827 0.3040 0.060 Uiso 1 1 calc R . . C8 C 0.2407(2) 0.08216(11) 0.07890(15) 0.0328(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Al1 0.0309(4) 0.0329(4) 0.0408(4) -0.0008(3) 0.0011(3) -0.0016(3) O1 0.0335(9) 0.0287(8) 0.0537(10) -0.0003(7) 0.0101(8) 0.0016(6) N1 0.0325(10) 0.0288(9) 0.0396(10) 0.0008(8) -0.0036(8) -0.0038(8) C2 0.0504(16) 0.0635(17) 0.0491(16) -0.0038(13) 0.0078(13) -0.0124(13) C1 0.0507(16) 0.0504(15) 0.0629(18) -0.0023(13) -0.0123(14) 0.0035(12) C10 0.0384(13) 0.0293(11) 0.0420(13) 0.0025(10) -0.0017(11) -0.0043(9) C11 0.0391(14) 0.0406(13) 0.0572(16) 0.0086(12) -0.0021(12) -0.0024(11) C6 0.0340(13) 0.0390(12) 0.0478(14) -0.0044(11) 0.0081(11) 0.0039(10) C3 0.0305(12) 0.0321(11) 0.0324(11) -0.0030(9) -0.0023(9) 0.0014(9) C15 0.0436(14) 0.0454(14) 0.0493(15) 0.0059(11) -0.0097(12) -0.0076(11) C9 0.0394(13) 0.0276(11) 0.0410(13) -0.0012(9) -0.0038(11) 0.0024(9) C5 0.0342(13) 0.0373(12) 0.0391(13) -0.0002(10) 0.0053(10) -0.0029(10) C4 0.0329(12) 0.0283(10) 0.0318(11) -0.0011(9) -0.0020(9) -0.0006(9) C7 0.0402(14) 0.0313(11) 0.0464(13) -0.0028(10) 0.0003(11) 0.0053(10) C14 0.0494(16) 0.0526(15) 0.0549(16) -0.0035(13) -0.0043(13) -0.0201(12) C13 0.0577(17) 0.0370(13) 0.0543(16) 0.0028(12) 0.0101(13) -0.0091(12) C12 0.0517(16) 0.0418(13) 0.0577(16) 0.0130(12) 0.0005(13) 0.0001(12) C8 0.0331(12) 0.0282(10) 0.0371(12) -0.0021(9) -0.0006(10) 0.0002(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 Al1 O1 1.7675(16) . ? Al1 C2 1.944(3) . ? Al1 C1 1.951(2) . ? Al1 N1 1.9688(18) . ? O1 C3 1.322(2) . ? N1 C9 1.303(3) . ? N1 C10 1.439(3) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C10 C11 1.381(3) . ? C10 C15 1.388(3) . ? C11 C12 1.389(3) . ? C11 H11A 0.9300 . ? C6 C7 1.369(3) . ? C6 C5 1.392(3) . ? C6 H6A 0.9300 . ? C3 C4 1.408(3) . ? C3 C8 1.419(3) . ? C15 C14 1.386(3) . ? C15 H15A 0.9300 . ? C9 C8 1.431(3) . ? C9 H9A 0.9300 . ? C5 C4 1.380(3) . ? C5 H5A 0.9300 . ? C4 C4 1.490(4) 2 ? C7 C8 1.398(3) . ? C7 H7A 0.9300 . ? C14 C13 1.376(3) . ? C14 H14A 0.9300 . ? C13 C12 1.371(3) . ? C13 H13A 0.9300 . ? C12 H12A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Al1 C2 111.85(10) . . ? O1 Al1 C1 109.05(10) . . ? C2 Al1 C1 119.95(12) . . ? O1 Al1 N1 94.53(7) . . ? C2 Al1 N1 106.31(11) . . ? C1 Al1 N1 112.22(10) . . ? C3 O1 Al1 131.79(13) . . ? C9 N1 C10 116.86(18) . . ? C9 N1 Al1 121.73(14) . . ? C10 N1 Al1 121.22(14) . . ? Al1 C2 H2A 109.5 . . ? Al1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? Al1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? Al1 C1 H1A 109.5 . . ? Al1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Al1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C11 C10 C15 119.5(2) . . ? C11 C10 N1 121.22(19) . . ? C15 C10 N1 119.2(2) . . ? C10 C11 C12 119.9(2) . . ? C10 C11 H11A 120.1 . . ? C12 C11 H11A 120.1 . . ? C7 C6 C5 119.3(2) . . ? C7 C6 H6A 120.4 . . ? C5 C6 H6A 120.4 . . ? O1 C3 C4 119.96(18) . . ? O1 C3 C8 121.17(19) . . ? C4 C3 C8 118.86(18) . . ? C14 C15 C10 119.8(2) . . ? C14 C15 H15A 120.1 . . ? C10 C15 H15A 120.1 . . ? N1 C9 C8 127.19(19) . . ? N1 C9 H9A 116.4 . . ? C8 C9 H9A 116.4 . . ? C4 C5 C6 122.0(2) . . ? C4 C5 H5A 119.0 . . ? C6 C5 H5A 119.0 . . ? C5 C4 C3 119.25(18) . . ? C5 C4 C4 121.4(2) . 2 ? C3 C4 C4 119.3(2) . 2 ? C6 C7 C8 120.9(2) . . ? C6 C7 H7A 119.6 . . ? C8 C7 H7A 119.6 . . ? C13 C14 C15 120.6(2) . . ? C13 C14 H14A 119.7 . . ? C15 C14 H14A 119.7 . . ? C12 C13 C14 119.6(2) . . ? C12 C13 H13A 120.2 . . ? C14 C13 H13A 120.2 . . ? C13 C12 C11 120.6(2) . . ? C13 C12 H12A 119.7 . . ? C11 C12 H12A 119.7 . . ? C7 C8 C3 119.72(19) . . ? C7 C8 C9 117.95(19) . . ? C3 C8 C9 122.33(19) . . ? 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 C2 Al1 O1 C3 121.8(2) . . . . ? C1 Al1 O1 C3 -103.1(2) . . . . ? N1 Al1 O1 C3 12.2(2) . . . . ? O1 Al1 N1 C9 -3.29(19) . . . . ? C2 Al1 N1 C9 -117.64(19) . . . . ? C1 Al1 N1 C9 109.41(19) . . . . ? O1 Al1 N1 C10 171.51(16) . . . . ? C2 Al1 N1 C10 57.17(18) . . . . ? C1 Al1 N1 C10 -75.78(19) . . . . ? C9 N1 C10 C11 46.7(3) . . . . ? Al1 N1 C10 C11 -128.3(2) . . . . ? C9 N1 C10 C15 -134.4(2) . . . . ? Al1 N1 C10 C15 50.5(3) . . . . ? C15 C10 C11 C12 3.4(4) . . . . ? N1 C10 C11 C12 -177.8(2) . . . . ? Al1 O1 C3 C4 168.06(15) . . . . ? Al1 O1 C3 C8 -13.1(3) . . . . ? C11 C10 C15 C14 -3.4(4) . . . . ? N1 C10 C15 C14 177.7(2) . . . . ? C10 N1 C9 C8 -179.2(2) . . . . ? Al1 N1 C9 C8 -4.2(3) . . . . ? C7 C6 C5 C4 0.6(4) . . . . ? C6 C5 C4 C3 -0.1(3) . . . . ? C6 C5 C4 C4 178.83(18) . . . 2 ? O1 C3 C4 C5 177.80(19) . . . . ? C8 C3 C4 C5 -1.1(3) . . . . ? O1 C3 C4 C4 -1.2(3) . . . 2 ? C8 C3 C4 C4 179.97(16) . . . 2 ? C5 C6 C7 C8 0.0(4) . . . . ? C10 C15 C14 C13 1.5(4) . . . . ? C15 C14 C13 C12 0.6(4) . . . . ? C14 C13 C12 C11 -0.6(4) . . . . ? C10 C11 C12 C13 -1.4(4) . . . . ? C6 C7 C8 C3 -1.2(3) . . . . ? C6 C7 C8 C9 179.3(2) . . . . ? O1 C3 C8 C7 -177.1(2) . . . . ? C4 C3 C8 C7 1.7(3) . . . . ? O1 C3 C8 C9 2.4(3) . . . . ? C4 C3 C8 C9 -178.8(2) . . . . ? N1 C9 C8 C7 -174.4(2) . . . . ? N1 C9 C8 C3 6.1(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.284 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 906287' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_hhl #TrackingRef '14733_web_deposit_cif_file_1_JingyuLiu_1350442429.2b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H56 Al2 Cl2 N2 O2' _chemical_formula_weight 757.76 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.7382(6) _cell_length_b 17.1151(6) _cell_length_c 15.2211(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4360.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.154 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.225 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9116 _exptl_absorpt_correction_T_max 0.9398 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22905 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 26.07 _reflns_number_total 4319 _reflns_number_gt 3425 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0610P)^2^+2.6780P] 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 4319 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1339 _refine_ls_wR_factor_gt 0.1229 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Al1 Al 0.17053(3) 0.28268(3) 0.57553(4) 0.02838(16) Uani 1 1 d . . . O1 O 0.09730(7) 0.25457(8) 0.65430(8) 0.0309(3) Uani 1 1 d . . . N1 N 0.25990(9) 0.28200(9) 0.66024(10) 0.0284(3) Uani 1 1 d . . . C9 C 0.25308(11) 0.24835(11) 0.73582(12) 0.0293(4) Uani 1 1 d . . . H9 H 0.2996 0.2471 0.7716 0.035 Uiso 1 1 calc R . . C3 C 0.10674(11) 0.21737(10) 0.72989(12) 0.0258(4) Uani 1 1 d . . . C8 C 0.18224(11) 0.21253(10) 0.77150(12) 0.0267(4) Uani 1 1 d . . . C4 C 0.03998(10) 0.18309(10) 0.77145(12) 0.0268(4) Uani 1 1 d . . . C7 C 0.19010(12) 0.17307(11) 0.85181(13) 0.0319(4) Uani 1 1 d . . . H7 H 0.2412 0.1693 0.8787 0.038 Uiso 1 1 calc R . . C5 C 0.05051(11) 0.14596(11) 0.85176(13) 0.0313(4) Uani 1 1 d . . . H5 H 0.0053 0.1239 0.8802 0.038 Uiso 1 1 calc R . . C10 C 0.33790(11) 0.31512(12) 0.63938(13) 0.0325(4) Uani 1 1 d . . . C11 C 0.39680(11) 0.26698(13) 0.60324(14) 0.0375(5) Uani 1 1 d . . . C6 C 0.12488(12) 0.13983(12) 0.89206(13) 0.0344(4) Uani 1 1 d . . . H6 H 0.1305 0.1131 0.9464 0.041 Uiso 1 1 calc R . . C2 C 0.18713(12) 0.19951(13) 0.48911(14) 0.0385(5) Uani 1 1 d . . . H2A H 0.1757 0.1488 0.5162 0.058 Uiso 1 1 calc R . . H2B H 0.2427 0.2005 0.4688 0.058 Uiso 1 1 calc R . . H2C H 0.1513 0.2076 0.4390 0.058 Uiso 1 1 calc R . . C12 C 0.47088(13) 0.30086(16) 0.58537(17) 0.0504(6) Uani 1 1 d . . . H12 H 0.5123 0.2697 0.5610 0.060 Uiso 1 1 calc R . . C15 C 0.35045(13) 0.39445(13) 0.65684(14) 0.0396(5) Uani 1 1 d . . . C16 C 0.28686(14) 0.44502(12) 0.69976(16) 0.0435(5) Uani 1 1 d . . . H16 H 0.2341 0.4188 0.6907 0.052 Uiso 1 1 calc R . . C1 C 0.15178(13) 0.38760(13) 0.52893(15) 0.0420(5) Uani 1 1 d . . . H1A H 0.1166 0.3843 0.4776 0.063 Uiso 1 1 calc R . . H1B H 0.2028 0.4111 0.5117 0.063 Uiso 1 1 calc R . . H1C H 0.1265 0.4200 0.5742 0.063 Uiso 1 1 calc R . . C19 C 0.38453(12) 0.18063(13) 0.58576(15) 0.0416(5) Uani 1 1 d . . . H19 H 0.3261 0.1695 0.5916 0.050 Uiso 1 1 calc R . . C14 C 0.42595(15) 0.42471(16) 0.63764(17) 0.0539(6) Uani 1 1 d . . . H14 H 0.4368 0.4782 0.6491 0.065 Uiso 1 1 calc R . . C20 C 0.41010(15) 0.15636(16) 0.49297(17) 0.0537(6) Uani 1 1 d . . . H20A H 0.3813 0.1880 0.4496 0.081 Uiso 1 1 calc R . . H20B H 0.3976 0.1010 0.4838 0.081 Uiso 1 1 calc R . . H20C H 0.4677 0.1646 0.4862 0.081 Uiso 1 1 calc R . . C13 C 0.48491(14) 0.37829(18) 0.60239(19) 0.0603(7) Uani 1 1 d . . . H13 H 0.5358 0.4001 0.5897 0.072 Uiso 1 1 calc R . . C21 C 0.42820(17) 0.13116(18) 0.6537(2) 0.0658(8) Uani 1 1 d . . . H21A H 0.4853 0.1436 0.6524 0.099 Uiso 1 1 calc R . . H21B H 0.4206 0.0757 0.6402 0.099 Uiso 1 1 calc R . . H21C H 0.4068 0.1424 0.7123 0.099 Uiso 1 1 calc R . . C17 C 0.30122(18) 0.45071(16) 0.79891(17) 0.0588(7) Uani 1 1 d . . . H17A H 0.3011 0.3982 0.8245 0.088 Uiso 1 1 calc R . . H17B H 0.2587 0.4820 0.8259 0.088 Uiso 1 1 calc R . . H17C H 0.3530 0.4756 0.8098 0.088 Uiso 1 1 calc R . . C18 C 0.28165(18) 0.52635(15) 0.6594(2) 0.0645(8) Uani 1 1 d . . . H18A H 0.3305 0.5556 0.6731 0.097 Uiso 1 1 calc R . . H18B H 0.2354 0.5539 0.6838 0.097 Uiso 1 1 calc R . . H18C H 0.2758 0.5219 0.5956 0.097 Uiso 1 1 calc R . . Cl1 Cl 0.07854(6) 0.45081(7) 0.78754(7) 0.1013(4) Uani 1 1 d . . . C22 C 0.0000 0.3963(3) 0.7500 0.0959(19) Uani 1 2 d S . . H22A H 0.0190 0.3621 0.7018 0.115 Uiso 0.50 1 calc PR . . H22B H -0.0190 0.3621 0.7982 0.115 Uiso 0.50 1 calc PR . . 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 0.0223(3) 0.0346(3) 0.0282(3) 0.0032(2) 0.0003(2) -0.0030(2) O1 0.0234(7) 0.0393(8) 0.0301(7) 0.0068(6) -0.0001(5) -0.0014(5) N1 0.0214(7) 0.0318(8) 0.0320(8) -0.0014(7) 0.0001(6) -0.0033(6) C9 0.0247(9) 0.0319(9) 0.0314(10) -0.0042(8) -0.0025(8) 0.0011(8) C3 0.0265(9) 0.0247(9) 0.0262(9) -0.0025(7) 0.0024(7) 0.0017(7) C8 0.0254(9) 0.0266(9) 0.0281(9) -0.0032(7) 0.0014(7) 0.0010(7) C4 0.0255(9) 0.0261(9) 0.0289(9) -0.0037(7) 0.0041(7) 0.0014(7) C7 0.0301(10) 0.0347(10) 0.0308(10) -0.0015(8) -0.0029(8) 0.0028(8) C5 0.0297(10) 0.0312(10) 0.0331(10) 0.0000(8) 0.0062(8) -0.0009(8) C10 0.0229(9) 0.0421(11) 0.0325(10) 0.0034(9) -0.0035(8) -0.0069(8) C11 0.0232(10) 0.0530(13) 0.0363(11) 0.0039(10) -0.0021(8) -0.0021(9) C6 0.0367(11) 0.0381(11) 0.0286(10) 0.0038(8) 0.0001(8) 0.0019(9) C2 0.0305(10) 0.0478(13) 0.0372(11) -0.0037(9) -0.0008(9) -0.0014(9) C12 0.0252(11) 0.0698(16) 0.0561(15) -0.0026(12) 0.0025(10) -0.0071(10) C15 0.0350(11) 0.0437(12) 0.0401(11) 0.0013(10) -0.0055(9) -0.0107(9) C16 0.0448(12) 0.0331(11) 0.0526(14) -0.0035(10) -0.0075(10) -0.0061(9) C1 0.0370(11) 0.0440(12) 0.0449(12) 0.0093(10) -0.0022(9) -0.0034(9) C19 0.0269(10) 0.0475(12) 0.0504(13) 0.0044(10) 0.0007(9) 0.0059(9) C14 0.0452(14) 0.0541(14) 0.0623(16) -0.0033(12) -0.0045(12) -0.0241(12) C20 0.0459(13) 0.0601(16) 0.0551(15) -0.0076(12) 0.0076(11) 0.0097(12) C13 0.0315(12) 0.084(2) 0.0658(17) -0.0021(15) 0.0043(11) -0.0222(13) C21 0.0612(17) 0.0689(18) 0.0674(18) 0.0143(15) -0.0086(14) 0.0171(14) C17 0.0702(17) 0.0522(15) 0.0540(15) -0.0087(12) -0.0060(13) 0.0003(13) C18 0.0761(19) 0.0400(14) 0.0774(19) 0.0021(13) -0.0149(15) -0.0072(13) Cl1 0.0816(6) 0.1162(8) 0.1061(7) 0.0492(6) -0.0054(5) -0.0119(5) C22 0.087(3) 0.051(2) 0.150(5) 0.000 0.066(3) 0.000 _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 1.7809(13) . ? Al1 C1 1.956(2) . ? Al1 C2 1.958(2) . ? Al1 N1 1.9750(16) . ? O1 C3 1.324(2) . ? N1 C9 1.292(2) . ? N1 C10 1.458(2) . ? C9 C8 1.441(3) . ? C9 H9 0.9500 . ? C3 C4 1.412(3) . ? C3 C8 1.416(2) . ? C8 C7 1.403(3) . ? C4 C5 1.389(3) . ? C4 C4 1.489(4) 3_556 ? C7 C6 1.375(3) . ? C7 H7 0.9500 . ? C5 C6 1.392(3) . ? C5 H5 0.9500 . ? C10 C11 1.398(3) . ? C10 C15 1.399(3) . ? C11 C12 1.396(3) . ? C11 C19 1.516(3) . ? C6 H6 0.9500 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C12 C13 1.371(4) . ? C12 H12 0.9500 . ? C15 C14 1.397(3) . ? C15 C16 1.519(3) . ? C16 C18 1.524(3) . ? C16 C17 1.531(3) . ? C16 H16 1.0000 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C19 C21 1.524(3) . ? C19 C20 1.533(3) . ? C19 H19 1.0000 . ? C14 C13 1.376(4) . ? C14 H14 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C13 H13 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? Cl1 C22 1.710(3) . ? C22 Cl1 1.710(3) 3_556 ? C22 H22A 0.9900 . ? C22 H22B 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 Al1 C1 112.44(8) . . ? O1 Al1 C2 110.70(8) . . ? C1 Al1 C2 116.53(10) . . ? O1 Al1 N1 94.60(7) . . ? C1 Al1 N1 111.33(8) . . ? C2 Al1 N1 109.08(8) . . ? C3 O1 Al1 129.25(11) . . ? C9 N1 C10 116.51(16) . . ? C9 N1 Al1 121.14(13) . . ? C10 N1 Al1 122.25(12) . . ? N1 C9 C8 126.73(17) . . ? N1 C9 H9 116.6 . . ? C8 C9 H9 116.6 . . ? O1 C3 C4 119.65(16) . . ? O1 C3 C8 121.54(16) . . ? C4 C3 C8 118.80(17) . . ? C7 C8 C3 120.11(17) . . ? C7 C8 C9 117.13(17) . . ? C3 C8 C9 122.75(17) . . ? C5 C4 C3 118.96(17) . . ? C5 C4 C4 120.00(18) . 3_556 ? C3 C4 C4 120.98(19) . 3_556 ? C6 C7 C8 120.86(18) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C4 C5 C6 122.40(18) . . ? C4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C11 C10 C15 122.74(19) . . ? C11 C10 N1 119.21(18) . . ? C15 C10 N1 118.05(18) . . ? C12 C11 C10 117.3(2) . . ? C12 C11 C19 119.4(2) . . ? C10 C11 C19 123.25(18) . . ? C7 C6 C5 118.86(18) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? Al1 C2 H2A 109.5 . . ? Al1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? Al1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C13 C12 C11 121.1(2) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C14 C15 C10 117.1(2) . . ? C14 C15 C16 120.8(2) . . ? C10 C15 C16 121.94(19) . . ? C15 C16 C18 112.8(2) . . ? C15 C16 C17 110.5(2) . . ? C18 C16 C17 110.3(2) . . ? C15 C16 H16 107.7 . . ? C18 C16 H16 107.7 . . ? C17 C16 H16 107.7 . . ? Al1 C1 H1A 109.5 . . ? Al1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Al1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C11 C19 C21 110.9(2) . . ? C11 C19 C20 112.8(2) . . ? C21 C19 C20 109.9(2) . . ? C11 C19 H19 107.6 . . ? C21 C19 H19 107.6 . . ? C20 C19 H19 107.6 . . ? C13 C14 C15 121.1(2) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C12 C13 C14 120.6(2) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? Cl1 C22 Cl1 113.9(3) 3_556 . ? Cl1 C22 H22A 108.8 3_556 . ? Cl1 C22 H22A 108.8 . . ? Cl1 C22 H22B 108.8 3_556 . ? Cl1 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.818 _refine_diff_density_min -0.713 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 906288' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_h #TrackingRef '14734_web_deposit_cif_file_2_JingyuLiu_1350442429.2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C55 H47 Al2 Cl3 N2 O2' _chemical_formula_weight 928.26 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' 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.0666(6) _cell_length_b 13.3996(6) _cell_length_c 28.7365(13) _cell_angle_alpha 90.00 _cell_angle_beta 102.3870(10) _cell_angle_gamma 90.00 _cell_volume 4914.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936 _exptl_absorpt_coefficient_mu 0.265 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9059 _exptl_absorpt_correction_T_max 0.9489 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24881 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 25.14 _reflns_number_total 8774 _reflns_number_gt 5764 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1876P)^2^+6.9966P] 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 8774 _refine_ls_number_parameters 581 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1266 _refine_ls_R_factor_gt 0.0902 _refine_ls_wR_factor_ref 0.3070 _refine_ls_wR_factor_gt 0.2687 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 Al2 Al 0.79141(10) 0.28682(10) 0.00495(5) 0.0280(3) Uani 1 1 d . . . Al1 Al 0.85987(11) -0.05106(10) 0.20012(5) 0.0317(4) Uani 1 1 d . . . O2 O 0.8250(2) 0.2242(2) 0.06142(10) 0.0298(7) Uani 1 1 d . . . O1 O 0.8695(2) 0.0522(2) 0.16171(11) 0.0324(7) Uani 1 1 d . . . N2 N 0.6504(3) 0.3230(3) 0.01534(13) 0.0286(8) Uani 1 1 d . . . N1 N 0.9561(3) -0.1335(3) 0.17089(13) 0.0312(8) Uani 1 1 d . . . Cl2 Cl 0.0585(2) 0.2593(3) 0.31322(11) 0.1399(11) Uani 1 1 d . . . C3 C 0.9606(3) 0.0842(3) 0.15478(15) 0.0280(9) Uani 1 1 d . . . Cl1 Cl 0.1819(3) 0.3657(3) 0.25561(13) 0.1610(13) Uani 1 1 d . . . C23 C 0.7223(4) 0.3322(3) 0.10012(15) 0.0301(10) Uani 1 1 d . . . C39 C 0.8474(4) -0.0407(4) 0.02807(17) 0.0372(11) Uani 1 1 d . . . H39 H 0.8110 0.0208 0.0273 0.045 Uiso 1 1 calc R . . C24 C 0.6399(4) 0.3425(3) 0.05836(16) 0.0302(10) Uani 1 1 d . . . H24 H 0.5735 0.3651 0.0625 0.036 Uiso 1 1 calc R . . C4 C 0.9737(4) 0.1865(3) 0.14598(15) 0.0306(10) Uani 1 1 d . . . C25 C 0.5564(3) 0.3212(3) -0.02181(16) 0.0308(10) Uani 1 1 d . . . C18 C 0.8108(3) 0.2696(3) 0.10039(16) 0.0287(10) Uani 1 1 d . . . C26 C 0.4797(4) 0.2483(3) -0.02169(17) 0.0337(10) Uani 1 1 d . . . C15 C 0.9196(4) -0.2643(3) 0.10963(18) 0.0360(11) Uani 1 1 d . . . C19 C 0.8824(3) 0.2551(3) 0.14419(16) 0.0303(10) Uani 1 1 d . . . C37 C 0.9104(4) -0.1930(3) 0.06930(16) 0.0327(10) Uani 1 1 d . . . C10 C 0.9401(4) -0.2376(3) 0.15815(17) 0.0328(10) Uani 1 1 d . . . C29 C 0.4610(4) 0.3845(4) -0.09679(18) 0.0402(12) Uani 1 1 d . . . H29 H 0.4549 0.4297 -0.1227 0.048 Uiso 1 1 calc R . . C41 C 0.9432(4) -0.1559(4) -0.00857(18) 0.0422(12) Uani 1 1 d . . . H41 H 0.9722 -0.1747 -0.0349 0.051 Uiso 1 1 calc R . . C5 C 1.0691(4) 0.2203(4) 0.13958(18) 0.0389(11) Uani 1 1 d . . . H5 H 1.0776 0.2896 0.1344 0.047 Uiso 1 1 calc R . . C43 C 0.4867(4) 0.1692(3) 0.01567(17) 0.0341(10) Uani 1 1 d . . . C8 C 1.0456(3) 0.0178(3) 0.15470(16) 0.0314(10) Uani 1 1 d . . . C7 C 1.1404(4) 0.0553(4) 0.14718(18) 0.0402(12) Uani 1 1 d . . . H7 H 1.1966 0.0106 0.1467 0.048 Uiso 1 1 calc R . . C30 C 0.5483(4) 0.3892(3) -0.05986(16) 0.0326(10) Uani 1 1 d . . . C38 C 0.8558(3) -0.1021(3) 0.06682(16) 0.0328(10) Uani 1 1 d . . . H38 H 0.8243 -0.0829 0.0923 0.039 Uiso 1 1 calc R . . C22 C 0.7095(4) 0.3763(4) 0.14232(17) 0.0379(11) Uani 1 1 d . . . H22 H 0.6492 0.4161 0.1421 0.045 Uiso 1 1 calc R . . C28 C 0.3829(4) 0.3157(4) -0.09676(18) 0.0433(12) Uani 1 1 d . . . H28 H 0.3225 0.3146 -0.1220 0.052 Uiso 1 1 calc R . . C50 C 0.6530(4) 0.5396(3) -0.02497(18) 0.0383(11) Uani 1 1 d . . . H50 H 0.6193 0.5378 0.0012 0.046 Uiso 1 1 calc R . . C48 C 0.3964(4) 0.1429(3) 0.03225(18) 0.0379(11) Uani 1 1 d . . . H48 H 0.3329 0.1784 0.0212 0.045 Uiso 1 1 calc R . . C20 C 0.8667(4) 0.3030(4) 0.18462(16) 0.0372(11) Uani 1 1 d . . . H20 H 0.9163 0.2936 0.2137 0.045 Uiso 1 1 calc R . . C47 C 0.3991(4) 0.0654(4) 0.06465(19) 0.0431(12) Uani 1 1 d . . . H47 H 0.3373 0.0484 0.0752 0.052 Uiso 1 1 calc R . . C49 C 0.6288(4) 0.4682(3) -0.06016(17) 0.0348(11) Uani 1 1 d . . . C42 C 0.9539(4) -0.2179(4) 0.03066(18) 0.0387(11) Uani 1 1 d . . . H42 H 0.9916 -0.2787 0.0312 0.046 Uiso 1 1 calc R . . C1 C 0.7207(4) -0.1109(4) 0.18477(19) 0.0422(12) Uani 1 1 d . . . H1A H 0.6715 -0.0689 0.1973 0.063 Uiso 1 1 calc R . . H1B H 0.7232 -0.1774 0.1991 0.063 Uiso 1 1 calc R . . H1C H 0.6973 -0.1165 0.1501 0.063 Uiso 1 1 calc R . . C6 C 1.1542(4) 0.1562(4) 0.1404(2) 0.0469(13) Uani 1 1 d . . . H6 H 1.2197 0.1814 0.1365 0.056 Uiso 1 1 calc R . . C9 C 1.0319(4) -0.0878(3) 0.15625(16) 0.0330(10) Uani 1 1 d . . . H9 H 1.0822 -0.1284 0.1457 0.040 Uiso 1 1 calc R . . C11 C 0.9417(4) -0.3085(4) 0.19370(19) 0.0437(12) Uani 1 1 d . . . C40 C 0.8905(4) -0.0667(4) -0.00934(18) 0.0412(12) Uani 1 1 d . . . H40 H 0.8842 -0.0234 -0.0360 0.049 Uiso 1 1 calc R . . C27 C 0.3930(4) 0.2484(4) -0.05979(18) 0.0395(12) Uani 1 1 d . . . H27 H 0.3392 0.2005 -0.0602 0.047 Uiso 1 1 calc R . . C21 C 0.7814(4) 0.3640(4) 0.18422(17) 0.0410(12) Uani 1 1 d . . . H21 H 0.7727 0.3967 0.2124 0.049 Uiso 1 1 calc R . . C45 C 0.5796(4) 0.0386(4) 0.06533(19) 0.0419(12) Uani 1 1 d . . . H45 H 0.6429 0.0031 0.0768 0.050 Uiso 1 1 calc R . . C2 C 0.9244(4) -0.0092(4) 0.26511(18) 0.0453(13) Uani 1 1 d . . . H2A H 0.9959 0.0144 0.2661 0.068 Uiso 1 1 calc R . . H2B H 0.9267 -0.0659 0.2868 0.068 Uiso 1 1 calc R . . H2C H 0.8831 0.0448 0.2749 0.068 Uiso 1 1 calc R . . C46 C 0.4897(4) 0.0131(4) 0.08160(19) 0.0435(12) Uani 1 1 d . . . H46 H 0.4913 -0.0394 0.1039 0.052 Uiso 1 1 calc R . . C12 C 0.9254(5) -0.4085(4) 0.1807(2) 0.0579(16) Uani 1 1 d . . . H12 H 0.9262 -0.4575 0.2047 0.070 Uiso 1 1 calc R . . C52 C 0.7760(5) 0.6167(4) -0.0651(2) 0.0557(15) Uani 1 1 d . . . H52 H 0.8264 0.6670 -0.0666 0.067 Uiso 1 1 calc R . . C44 C 0.5778(4) 0.1148(3) 0.03272(17) 0.0358(11) Uani 1 1 d . . . H44 H 0.6396 0.1302 0.0218 0.043 Uiso 1 1 calc R . . C51 C 0.7256(4) 0.6140(4) -0.0271(2) 0.0458(13) Uani 1 1 d . . . H51 H 0.7408 0.6630 -0.0027 0.055 Uiso 1 1 calc R . . C31 C 0.9616(5) -0.2853(4) 0.24503(19) 0.0503(14) Uani 1 1 d . . . C14 C 0.9050(5) -0.3656(4) 0.0986(2) 0.0483(13) Uani 1 1 d . . . H14 H 0.8926 -0.3860 0.0662 0.058 Uiso 1 1 calc R . . C13 C 0.9083(6) -0.4368(4) 0.1336(2) 0.0618(17) Uani 1 1 d . . . H13 H 0.8987 -0.5053 0.1253 0.074 Uiso 1 1 calc R . . C53 C 0.7524(6) 0.5462(5) -0.1003(2) 0.0645(17) Uani 1 1 d . . . H53 H 0.7868 0.5481 -0.1262 0.077 Uiso 1 1 calc R . . C54 C 0.6792(5) 0.4721(4) -0.0987(2) 0.0512(14) Uani 1 1 d . . . H54 H 0.6631 0.4241 -0.1235 0.061 Uiso 1 1 calc R . . C34 C 1.0066(13) -0.2608(9) 0.3432(3) 0.129(6) Uani 1 1 d . . . H34 H 1.0225 -0.2536 0.3769 0.154 Uiso 1 1 calc R . . C35 C 1.0733(8) -0.2228(6) 0.3167(3) 0.098(3) Uani 1 1 d . . . H35 H 1.1351 -0.1886 0.3320 0.118 Uiso 1 1 calc R . . C36 C 1.0499(6) -0.2346(5) 0.2671(2) 0.0664(19) Uani 1 1 d . . . H36 H 1.0955 -0.2074 0.2486 0.080 Uiso 1 1 calc R . . C32 C 0.8954(7) -0.3223(5) 0.2734(2) 0.075(2) Uani 1 1 d . . . H32 H 0.8336 -0.3574 0.2591 0.090 Uiso 1 1 calc R . . C33 C 0.9193(12) -0.3080(7) 0.3217(3) 0.121(5) Uani 1 1 d . . . H33 H 0.8726 -0.3323 0.3403 0.145 Uiso 1 1 calc R . . C55 C 0.1487(8) 0.2511(9) 0.2754(4) 0.123(4) Uani 1 1 d . . . H55 H 0.1137 0.2124 0.2466 0.147 Uiso 1 1 calc R . . Cl3 Cl 0.2587(3) 0.1845(4) 0.30246(16) 0.1837(17) Uani 1 1 d . . . C16 C 0.8836(4) 0.4028(4) 0.01117(19) 0.0390(11) Uani 1 1 d . . . H16A H 0.8580 0.4542 0.0301 0.059 Uiso 1 1 calc R . . H16B H 0.8845 0.4293 -0.0205 0.059 Uiso 1 1 calc R . . H16C H 0.9548 0.3831 0.0271 0.059 Uiso 1 1 calc R . . C17 C 0.7665(4) 0.1984(4) -0.05056(17) 0.0379(11) Uani 1 1 d . . . H17A H 0.8222 0.1481 -0.0467 0.057 Uiso 1 1 calc R . . H17B H 0.7662 0.2376 -0.0794 0.057 Uiso 1 1 calc R . . H17C H 0.6987 0.1651 -0.0534 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 Al2 0.0307(7) 0.0255(7) 0.0287(7) -0.0015(5) 0.0082(6) 0.0005(5) Al1 0.0360(8) 0.0276(7) 0.0329(8) -0.0016(6) 0.0106(6) -0.0046(6) O2 0.0336(17) 0.0276(16) 0.0276(16) -0.0022(13) 0.0054(13) 0.0037(12) O1 0.0307(16) 0.0278(17) 0.0399(18) 0.0029(13) 0.0100(14) -0.0005(13) N2 0.032(2) 0.0238(19) 0.030(2) -0.0008(15) 0.0057(16) 0.0002(15) N1 0.038(2) 0.027(2) 0.030(2) 0.0021(16) 0.0075(16) 0.0014(16) Cl2 0.112(2) 0.182(3) 0.118(2) 0.019(2) 0.0092(17) -0.007(2) C3 0.031(2) 0.031(2) 0.021(2) 0.0001(18) 0.0034(17) -0.0077(18) Cl1 0.165(3) 0.165(3) 0.145(3) 0.022(2) 0.015(2) -0.016(2) C23 0.037(2) 0.028(2) 0.027(2) 0.0008(18) 0.0093(19) -0.0020(18) C39 0.033(2) 0.033(3) 0.043(3) 0.002(2) 0.002(2) 0.0029(19) C24 0.035(2) 0.022(2) 0.034(3) 0.0020(18) 0.010(2) 0.0035(18) C4 0.037(2) 0.031(2) 0.023(2) 0.0034(18) 0.0037(19) -0.0031(19) C25 0.031(2) 0.029(2) 0.032(2) -0.0055(19) 0.0069(19) 0.0024(18) C18 0.032(2) 0.021(2) 0.033(2) 0.0007(18) 0.0094(19) -0.0058(17) C26 0.034(2) 0.030(2) 0.037(3) -0.004(2) 0.007(2) 0.0018(19) C15 0.040(3) 0.029(3) 0.041(3) -0.002(2) 0.014(2) -0.002(2) C19 0.037(2) 0.026(2) 0.028(2) 0.0037(18) 0.007(2) -0.0059(18) C37 0.032(2) 0.030(2) 0.036(3) -0.0044(19) 0.007(2) -0.0049(18) C10 0.037(3) 0.025(2) 0.038(3) 0.0021(19) 0.012(2) -0.0016(18) C29 0.045(3) 0.037(3) 0.035(3) 0.005(2) 0.002(2) 0.007(2) C41 0.042(3) 0.052(3) 0.036(3) -0.003(2) 0.015(2) -0.004(2) C5 0.040(3) 0.035(3) 0.043(3) 0.007(2) 0.010(2) -0.009(2) C43 0.036(3) 0.029(2) 0.037(3) -0.0058(19) 0.005(2) -0.0005(19) C8 0.028(2) 0.034(2) 0.032(2) 0.0001(19) 0.0053(19) -0.0033(18) C7 0.031(2) 0.043(3) 0.048(3) 0.005(2) 0.011(2) -0.001(2) C30 0.035(2) 0.031(2) 0.031(2) 0.0002(19) 0.008(2) 0.0070(19) C38 0.032(2) 0.036(3) 0.032(2) -0.004(2) 0.0090(19) -0.0031(19) C22 0.045(3) 0.034(3) 0.038(3) 0.000(2) 0.016(2) 0.006(2) C28 0.041(3) 0.043(3) 0.040(3) -0.003(2) -0.004(2) 0.007(2) C50 0.040(3) 0.032(3) 0.044(3) 0.001(2) 0.010(2) 0.004(2) C48 0.038(3) 0.029(2) 0.048(3) -0.003(2) 0.011(2) -0.001(2) C20 0.045(3) 0.040(3) 0.025(2) 0.003(2) 0.004(2) -0.003(2) C47 0.045(3) 0.040(3) 0.046(3) -0.005(2) 0.014(2) -0.008(2) C49 0.040(3) 0.030(2) 0.034(3) 0.007(2) 0.007(2) 0.004(2) C42 0.037(3) 0.037(3) 0.044(3) -0.003(2) 0.012(2) 0.000(2) C1 0.047(3) 0.039(3) 0.042(3) 0.001(2) 0.014(2) -0.011(2) C6 0.036(3) 0.044(3) 0.062(4) 0.009(3) 0.013(2) -0.007(2) C9 0.029(2) 0.036(3) 0.033(2) 0.001(2) 0.0033(19) 0.0036(19) C11 0.055(3) 0.035(3) 0.042(3) 0.004(2) 0.012(2) 0.002(2) C40 0.040(3) 0.045(3) 0.039(3) 0.003(2) 0.009(2) -0.004(2) C27 0.035(3) 0.033(3) 0.048(3) -0.005(2) 0.002(2) -0.003(2) C21 0.053(3) 0.046(3) 0.025(2) -0.005(2) 0.012(2) 0.004(2) C45 0.044(3) 0.030(3) 0.051(3) 0.005(2) 0.008(2) 0.004(2) C2 0.054(3) 0.045(3) 0.038(3) -0.005(2) 0.014(2) 0.001(2) C46 0.055(3) 0.029(3) 0.048(3) 0.003(2) 0.013(3) -0.005(2) C12 0.091(5) 0.032(3) 0.056(4) 0.008(3) 0.026(3) -0.003(3) C52 0.060(4) 0.042(3) 0.064(4) 0.016(3) 0.011(3) -0.008(3) C44 0.033(2) 0.032(3) 0.043(3) -0.001(2) 0.009(2) -0.0035(19) C51 0.053(3) 0.030(3) 0.051(3) 0.004(2) 0.004(3) 0.003(2) C31 0.078(4) 0.036(3) 0.037(3) 0.005(2) 0.013(3) 0.019(3) C14 0.071(4) 0.030(3) 0.045(3) -0.004(2) 0.014(3) -0.006(2) C13 0.104(5) 0.023(3) 0.059(4) -0.002(2) 0.019(4) -0.009(3) C53 0.082(5) 0.061(4) 0.057(4) 0.016(3) 0.028(3) -0.015(3) C54 0.063(4) 0.051(3) 0.043(3) 0.004(3) 0.018(3) -0.004(3) C34 0.241(15) 0.114(8) 0.023(4) 0.013(4) 0.011(6) 0.122(9) C35 0.129(8) 0.088(6) 0.056(5) -0.012(4) -0.028(5) 0.064(5) C36 0.089(5) 0.057(4) 0.049(4) -0.001(3) 0.006(3) 0.035(4) C32 0.129(7) 0.048(4) 0.061(4) 0.023(3) 0.049(4) 0.030(4) C33 0.240(14) 0.088(7) 0.047(5) 0.035(5) 0.059(7) 0.095(8) C55 0.099(7) 0.155(10) 0.112(8) 0.044(7) 0.018(6) 0.008(7) Cl3 0.150(3) 0.217(4) 0.202(4) 0.081(3) 0.079(3) 0.005(3) C16 0.035(3) 0.032(3) 0.051(3) 0.000(2) 0.010(2) 0.003(2) C17 0.044(3) 0.036(3) 0.033(3) -0.004(2) 0.007(2) 0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Al2 O2 1.795(3) . ? Al2 C16 1.951(5) . ? Al2 C17 1.958(5) . ? Al2 N2 1.989(4) . ? Al1 O1 1.791(3) . ? Al1 C1 1.950(5) . ? Al1 C2 1.959(5) . ? Al1 N1 1.990(4) . ? O2 C18 1.322(5) . ? O1 C3 1.319(5) . ? N2 C24 1.299(6) . ? N2 C25 1.445(6) . ? N1 C9 1.308(6) . ? N1 C10 1.446(6) . ? Cl2 C55 1.771(11) . ? C3 C4 1.411(6) . ? C3 C8 1.424(6) . ? Cl1 C55 1.724(11) . ? C23 C22 1.391(6) . ? C23 C18 1.427(6) . ? C23 C24 1.436(6) . ? C39 C40 1.361(7) . ? C39 C38 1.369(7) . ? C39 H39 0.9500 . ? C24 H24 0.9500 . ? C4 C5 1.375(6) . ? C4 C19 1.498(6) . ? C25 C26 1.399(6) . ? C25 C30 1.410(6) . ? C18 C19 1.411(6) . ? C26 C27 1.397(7) . ? C26 C43 1.497(7) . ? C15 C14 1.398(7) . ? C15 C10 1.408(7) . ? C15 C37 1.486(7) . ? C19 C20 1.381(6) . ? C37 C42 1.392(7) . ? C37 C38 1.407(6) . ? C10 C11 1.392(7) . ? C29 C28 1.375(7) . ? C29 C30 1.383(7) . ? C29 H29 0.9500 . ? C41 C40 1.376(7) . ? C41 C42 1.384(7) . ? C41 H41 0.9500 . ? C5 C6 1.401(7) . ? C5 H5 0.9500 . ? C43 C44 1.392(7) . ? C43 C48 1.410(7) . ? C8 C7 1.396(6) . ? C8 C9 1.429(6) . ? C7 C6 1.383(7) . ? C7 H7 0.9500 . ? C30 C49 1.494(7) . ? C38 H38 0.9500 . ? C22 C21 1.369(7) . ? C22 H22 0.9500 . ? C28 C27 1.378(7) . ? C28 H28 0.9500 . ? C50 C49 1.379(7) . ? C50 C51 1.386(7) . ? C50 H50 0.9500 . ? C48 C47 1.390(7) . ? C48 H48 0.9500 . ? C20 C21 1.380(7) . ? C20 H20 0.9500 . ? C47 C46 1.373(8) . ? C47 H47 0.9500 . ? C49 C54 1.404(7) . ? C42 H42 0.9500 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C6 H6 0.9500 . ? C9 H9 0.9500 . ? C11 C12 1.394(7) . ? C11 C31 1.475(7) . ? C40 H40 0.9500 . ? C27 H27 0.9500 . ? C21 H21 0.9500 . ? C45 C44 1.383(7) . ? C45 C46 1.396(7) . ? C45 H45 0.9500 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C46 H46 0.9500 . ? C12 C13 1.377(8) . ? C12 H12 0.9500 . ? C52 C53 1.370(9) . ? C52 C51 1.392(8) . ? C52 H52 0.9500 . ? C44 H44 0.9500 . ? C51 H51 0.9500 . ? C31 C36 1.372(9) . ? C31 C32 1.400(9) . ? C14 C13 1.381(8) . ? C14 H14 0.9500 . ? C13 H13 0.9500 . ? C53 C54 1.387(8) . ? C53 H53 0.9500 . ? C54 H54 0.9500 . ? C34 C33 1.335(18) . ? C34 C35 1.373(16) . ? C34 H34 0.9500 . ? C35 C36 1.404(10) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C32 C33 1.368(11) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C55 Cl3 1.729(11) . ? C55 H55 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Al2 C16 105.24(19) . . ? O2 Al2 C17 114.79(19) . . ? C16 Al2 C17 123.3(2) . . ? O2 Al2 N2 91.88(15) . . ? C16 Al2 N2 111.46(18) . . ? C17 Al2 N2 105.82(19) . . ? O1 Al1 C1 111.3(2) . . ? O1 Al1 C2 107.1(2) . . ? C1 Al1 C2 121.6(2) . . ? O1 Al1 N1 91.95(15) . . ? C1 Al1 N1 108.6(2) . . ? C2 Al1 N1 112.3(2) . . ? C18 O2 Al2 120.0(3) . . ? C3 O1 Al1 122.0(3) . . ? C24 N2 C25 117.4(4) . . ? C24 N2 Al2 118.8(3) . . ? C25 N2 Al2 123.6(3) . . ? C9 N1 C10 116.6(4) . . ? C9 N1 Al1 117.8(3) . . ? C10 N1 Al1 124.9(3) . . ? O1 C3 C4 119.4(4) . . ? O1 C3 C8 121.7(4) . . ? C4 C3 C8 118.8(4) . . ? C22 C23 C18 119.6(4) . . ? C22 C23 C24 118.6(4) . . ? C18 C23 C24 121.5(4) . . ? C40 C39 C38 121.0(5) . . ? C40 C39 H39 119.5 . . ? C38 C39 H39 119.5 . . ? N2 C24 C23 124.2(4) . . ? N2 C24 H24 117.9 . . ? C23 C24 H24 117.9 . . ? C5 C4 C3 119.5(4) . . ? C5 C4 C19 122.1(4) . . ? C3 C4 C19 118.4(4) . . ? C26 C25 C30 121.2(4) . . ? C26 C25 N2 120.4(4) . . ? C30 C25 N2 118.2(4) . . ? O2 C18 C19 120.4(4) . . ? O2 C18 C23 121.8(4) . . ? C19 C18 C23 117.9(4) . . ? C27 C26 C25 117.3(4) . . ? C27 C26 C43 118.5(4) . . ? C25 C26 C43 124.2(4) . . ? C14 C15 C10 117.3(4) . . ? C14 C15 C37 117.6(4) . . ? C10 C15 C37 125.1(4) . . ? C20 C19 C18 119.8(4) . . ? C20 C19 C4 121.2(4) . . ? C18 C19 C4 119.1(4) . . ? C42 C37 C38 117.2(4) . . ? C42 C37 C15 119.4(4) . . ? C38 C37 C15 123.4(4) . . ? C11 C10 C15 121.5(4) . . ? C11 C10 N1 119.6(4) . . ? C15 C10 N1 118.8(4) . . ? C28 C29 C30 121.4(5) . . ? C28 C29 H29 119.3 . . ? C30 C29 H29 119.3 . . ? C40 C41 C42 119.8(5) . . ? C40 C41 H41 120.1 . . ? C42 C41 H41 120.1 . . ? C4 C5 C6 122.3(4) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C44 C43 C48 117.7(4) . . ? C44 C43 C26 122.6(4) . . ? C48 C43 C26 119.5(4) . . ? C7 C8 C3 119.6(4) . . ? C7 C8 C9 118.9(4) . . ? C3 C8 C9 121.1(4) . . ? C6 C7 C8 121.3(5) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C29 C30 C25 118.5(4) . . ? C29 C30 C49 119.6(4) . . ? C25 C30 C49 121.8(4) . . ? C39 C38 C37 120.8(4) . . ? C39 C38 H38 119.6 . . ? C37 C38 H38 119.6 . . ? C21 C22 C23 121.9(5) . . ? C21 C22 H22 119.1 . . ? C23 C22 H22 119.1 . . ? C29 C28 C27 119.4(5) . . ? C29 C28 H28 120.3 . . ? C27 C28 H28 120.3 . . ? C49 C50 C51 121.2(5) . . ? C49 C50 H50 119.4 . . ? C51 C50 H50 119.4 . . ? C47 C48 C43 120.7(5) . . ? C47 C48 H48 119.7 . . ? C43 C48 H48 119.7 . . ? C21 C20 C19 122.3(4) . . ? C21 C20 H20 118.9 . . ? C19 C20 H20 118.9 . . ? C46 C47 C48 121.0(5) . . ? C46 C47 H47 119.5 . . ? C48 C47 H47 119.5 . . ? C50 C49 C54 118.7(5) . . ? C50 C49 C30 122.6(4) . . ? C54 C49 C30 118.7(4) . . ? C41 C42 C37 121.3(5) . . ? C41 C42 H42 119.4 . . ? C37 C42 H42 119.4 . . ? Al1 C1 H1A 109.5 . . ? Al1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Al1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C6 C5 118.4(5) . . ? C7 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? N1 C9 C8 125.6(4) . . ? N1 C9 H9 117.2 . . ? C8 C9 H9 117.2 . . ? C10 C11 C12 118.8(5) . . ? C10 C11 C31 124.2(5) . . ? C12 C11 C31 117.0(5) . . ? C39 C40 C41 120.0(5) . . ? C39 C40 H40 120.0 . . ? C41 C40 H40 120.0 . . ? C28 C27 C26 122.2(5) . . ? C28 C27 H27 118.9 . . ? C26 C27 H27 118.9 . . ? C22 C21 C20 118.6(4) . . ? C22 C21 H21 120.7 . . ? C20 C21 H21 120.7 . . ? C44 C45 C46 121.0(5) . . ? C44 C45 H45 119.5 . . ? C46 C45 H45 119.5 . . ? Al1 C2 H2A 109.5 . . ? Al1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? Al1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C47 C46 C45 118.7(5) . . ? C47 C46 H46 120.7 . . ? C45 C46 H46 120.7 . . ? C13 C12 C11 120.7(5) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C53 C52 C51 119.5(5) . . ? C53 C52 H52 120.3 . . ? C51 C52 H52 120.3 . . ? C45 C44 C43 120.9(4) . . ? C45 C44 H44 119.5 . . ? C43 C44 H44 119.5 . . ? C50 C51 C52 119.8(5) . . ? C50 C51 H51 120.1 . . ? C52 C51 H51 120.1 . . ? C36 C31 C32 118.0(6) . . ? C36 C31 C11 121.1(6) . . ? C32 C31 C11 120.7(6) . . ? C13 C14 C15 121.6(5) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C12 C13 C14 119.9(5) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C52 C53 C54 121.1(6) . . ? C52 C53 H53 119.5 . . ? C54 C53 H53 119.5 . . ? C53 C54 C49 119.8(6) . . ? C53 C54 H54 120.1 . . ? C49 C54 H54 120.1 . . ? C33 C34 C35 120.0(8) . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? C34 C35 C36 119.8(10) . . ? C34 C35 H35 120.1 . . ? C36 C35 H35 120.1 . . ? C31 C36 C35 120.2(8) . . ? C31 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? C33 C32 C31 120.4(10) . . ? C33 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? C34 C33 C32 121.5(11) . . ? C34 C33 H33 119.2 . . ? C32 C33 H33 119.2 . . ? Cl1 C55 Cl3 111.4(6) . . ? Cl1 C55 Cl2 113.3(7) . . ? Cl3 C55 Cl2 110.7(6) . . ? Cl1 C55 H55 107.0 . . ? Cl3 C55 H55 107.0 . . ? Cl2 C55 H55 107.0 . . ? Al2 C16 H16A 109.5 . . ? Al2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? Al2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? Al2 C17 H17A 109.5 . . ? Al2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? Al2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.435 _refine_diff_density_min -0.946 _refine_diff_density_rms 0.113 _database_code_depnum_ccdc_archive 'CCDC 906289' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_h1 #TrackingRef '14735_web_deposit_cif_file_3_JingyuLiu_1350442429.2d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H50 Al2 Cl0 N2 O2' _chemical_formula_weight 620.76 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' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.8192(9) _cell_length_b 13.1067(8) _cell_length_c 18.7852(11) _cell_angle_alpha 90.00 _cell_angle_beta 104.5450(10) _cell_angle_gamma 90.00 _cell_volume 3770.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.094 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9679 _exptl_absorpt_correction_T_max 0.9838 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10305 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 26.09 _reflns_number_total 3735 _reflns_number_gt 2854 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; 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 0.500 0.000 0.396 392 78 ' ' 2 0.000 0.500 0.279 392 78 ' ' _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^)+(0.0650P)^2^+1.5825P] 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 3735 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1325 _refine_ls_wR_factor_gt 0.1262 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 Al1 Al 0.24224(3) 0.57786(4) 0.36318(3) 0.02623(17) Uani 1 1 d . . . N1 N 0.21659(10) 0.57510(12) 0.46122(8) 0.0255(3) Uani 1 1 d . . . O1 O 0.13973(8) 0.62900(11) 0.31654(7) 0.0321(3) Uani 1 1 d . . . C4 C 0.00165(11) 0.70857(13) 0.28970(9) 0.0234(4) Uani 1 1 d . . . C3 C 0.07511(11) 0.66789(13) 0.34068(10) 0.0243(4) Uani 1 1 d . . . C9 C 0.14578(12) 0.61674(15) 0.47065(10) 0.0287(4) Uani 1 1 d . . . H9 H 0.1385 0.6153 0.5193 0.034 Uiso 1 1 calc R . . C8 C 0.07708(12) 0.66472(14) 0.41635(10) 0.0270(4) Uani 1 1 d . . . C5 C -0.06687(12) 0.74584(14) 0.31596(10) 0.0285(4) Uani 1 1 d . . . H5 H -0.1168 0.7729 0.2821 0.034 Uiso 1 1 calc R . . C7 C 0.00610(12) 0.70468(16) 0.44001(11) 0.0330(5) Uani 1 1 d . . . H7 H 0.0074 0.7038 0.4908 0.040 Uiso 1 1 calc R . . C15 C 0.23545(14) 0.41559(15) 0.53197(12) 0.0359(5) Uani 1 1 d . . . H15A H 0.2258 0.3785 0.4847 0.043 Uiso 1 1 calc R . . H15B H 0.1782 0.4243 0.5437 0.043 Uiso 1 1 calc R . . C11 C 0.28842(15) 0.57676(17) 0.59823(11) 0.0394(5) Uani 1 1 d . . . H11A H 0.2314 0.5862 0.6102 0.047 Uiso 1 1 calc R . . H11B H 0.3140 0.6449 0.5945 0.047 Uiso 1 1 calc R . . C6 C -0.06455(13) 0.74471(16) 0.39058(11) 0.0342(5) Uani 1 1 d . . . H6 H -0.1120 0.7717 0.4071 0.041 Uiso 1 1 calc R . . C17 C 0.36415(13) 0.50674(19) 0.50851(11) 0.0396(5) Uani 1 1 d . . . H17A H 0.3906 0.5745 0.5052 0.048 Uiso 1 1 calc R . . H17B H 0.3569 0.4720 0.4606 0.048 Uiso 1 1 calc R . . C16 C 0.42498(14) 0.4435(2) 0.56916(12) 0.0437(6) Uani 1 1 d . . . H16 H 0.4825 0.4341 0.5571 0.052 Uiso 1 1 calc R . . C10 C 0.27536(12) 0.52010(14) 0.52492(10) 0.0269(4) Uani 1 1 d . . . C2 C 0.24912(16) 0.44026(17) 0.32420(12) 0.0416(5) Uani 1 1 d . . . H2A H 0.2192 0.3921 0.3495 0.062 Uiso 1 1 calc R . . H2B H 0.3105 0.4203 0.3323 0.062 Uiso 1 1 calc R . . H2C H 0.2211 0.4396 0.2714 0.062 Uiso 1 1 calc R . . C12 C 0.35001(15) 0.51413(19) 0.65924(12) 0.0441(6) Uani 1 1 d . . . H12 H 0.3583 0.5509 0.7072 0.053 Uiso 1 1 calc R . . C13 C 0.30940(16) 0.41064(19) 0.66499(12) 0.0455(6) Uani 1 1 d . . . H13A H 0.3479 0.3707 0.7050 0.055 Uiso 1 1 calc R . . H13B H 0.2523 0.4196 0.6769 0.055 Uiso 1 1 calc R . . C14 C 0.29668(15) 0.35371(17) 0.59292(12) 0.0425(5) Uani 1 1 d . . . H14 H 0.2703 0.2853 0.5971 0.051 Uiso 1 1 calc R . . C19 C 0.43839(15) 0.5008(2) 0.64176(13) 0.0512(6) Uani 1 1 d . . . H19A H 0.4783 0.4619 0.6816 0.061 Uiso 1 1 calc R . . H19B H 0.4649 0.5683 0.6379 0.061 Uiso 1 1 calc R . . C1 C 0.33449(14) 0.67723(17) 0.36390(12) 0.0382(5) Uani 1 1 d . . . H1A H 0.3139 0.7270 0.3244 0.057 Uiso 1 1 calc R . . H1B H 0.3861 0.6420 0.3563 0.057 Uiso 1 1 calc R . . H1C H 0.3496 0.7126 0.4114 0.057 Uiso 1 1 calc R . . C18 C 0.38413(16) 0.34017(18) 0.57454(12) 0.0458(6) Uani 1 1 d . . . H18A H 0.4234 0.2989 0.6132 0.055 Uiso 1 1 calc R . . H18B H 0.3758 0.3035 0.5272 0.055 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 0.0242(3) 0.0328(3) 0.0226(3) 0.0020(2) 0.0075(2) 0.0069(2) N1 0.0252(8) 0.0311(8) 0.0199(8) 0.0019(7) 0.0049(6) 0.0018(6) O1 0.0266(7) 0.0485(8) 0.0217(7) 0.0028(6) 0.0073(5) 0.0126(6) C4 0.0233(8) 0.0216(8) 0.0244(9) -0.0013(7) 0.0044(7) -0.0021(7) C3 0.0206(8) 0.0258(9) 0.0272(9) -0.0019(8) 0.0069(7) 0.0010(7) C9 0.0283(9) 0.0357(10) 0.0229(9) -0.0013(8) 0.0080(8) 0.0018(8) C8 0.0243(9) 0.0337(10) 0.0229(9) -0.0014(8) 0.0057(8) 0.0024(7) C5 0.0238(9) 0.0317(10) 0.0289(10) 0.0020(8) 0.0043(8) 0.0050(7) C7 0.0313(10) 0.0436(11) 0.0253(10) -0.0006(9) 0.0095(8) 0.0051(9) C15 0.0391(11) 0.0330(11) 0.0346(11) 0.0026(9) 0.0071(9) -0.0013(9) C11 0.0467(12) 0.0378(12) 0.0300(11) -0.0043(9) 0.0025(10) 0.0060(9) C6 0.0288(10) 0.0434(12) 0.0326(11) -0.0022(9) 0.0118(9) 0.0094(9) C17 0.0278(10) 0.0599(14) 0.0317(11) 0.0154(10) 0.0086(9) 0.0083(9) C16 0.0293(11) 0.0718(16) 0.0302(11) 0.0150(11) 0.0077(9) 0.0145(10) C10 0.0266(9) 0.0309(10) 0.0223(9) 0.0033(8) 0.0044(7) 0.0035(7) C2 0.0529(13) 0.0414(12) 0.0311(11) 0.0013(10) 0.0117(10) 0.0114(10) C12 0.0501(13) 0.0540(14) 0.0233(10) -0.0071(10) -0.0002(9) 0.0136(11) C13 0.0506(13) 0.0614(15) 0.0272(11) 0.0144(11) 0.0146(10) 0.0145(11) C14 0.0541(13) 0.0342(11) 0.0397(12) 0.0095(10) 0.0129(11) 0.0042(10) C19 0.0389(12) 0.0627(15) 0.0416(13) 0.0099(12) -0.0093(10) 0.0006(11) C1 0.0333(11) 0.0480(13) 0.0333(11) 0.0062(10) 0.0085(9) 0.0023(9) C18 0.0573(14) 0.0495(13) 0.0291(11) 0.0066(10) 0.0083(10) 0.0242(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 Al1 O1 1.7701(13) . ? Al1 C1 1.953(2) . ? Al1 C2 1.960(2) . ? Al1 N1 1.9832(16) . ? N1 C9 1.298(2) . ? N1 C10 1.502(2) . ? O1 C3 1.320(2) . ? C4 C5 1.388(2) . ? C4 C3 1.412(2) . ? C4 C4 1.479(3) 2 ? C3 C8 1.415(3) . ? C9 C8 1.435(3) . ? C9 H9 0.9500 . ? C8 C7 1.408(3) . ? C5 C6 1.393(3) . ? C5 H5 0.9500 . ? C7 C6 1.366(3) . ? C7 H7 0.9500 . ? C15 C10 1.528(3) . ? C15 C14 1.533(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C11 C10 1.532(3) . ? C11 C12 1.541(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C6 H6 0.9500 . ? C17 C10 1.522(3) . ? C17 C16 1.537(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C16 C18 1.514(4) . ? C16 C19 1.524(3) . ? C16 H16 1.0000 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C12 C13 1.516(4) . ? C12 C19 1.524(3) . ? C12 H12 1.0000 . ? C13 C14 1.514(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C18 1.518(3) . ? C14 H14 1.0000 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C18 H18A 0.9900 . ? C18 H18B 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 Al1 C1 109.93(8) . . ? O1 Al1 C2 107.06(9) . . ? C1 Al1 C2 120.31(10) . . ? O1 Al1 N1 95.22(6) . . ? C1 Al1 N1 109.42(8) . . ? C2 Al1 N1 111.94(8) . . ? C9 N1 C10 118.41(15) . . ? C9 N1 Al1 120.27(13) . . ? C10 N1 Al1 121.23(11) . . ? C3 O1 Al1 131.93(12) . . ? C5 C4 C3 118.38(16) . . ? C5 C4 C4 121.71(18) . 2 ? C3 C4 C4 119.90(18) . 2 ? O1 C3 C4 119.30(16) . . ? O1 C3 C8 120.68(16) . . ? C4 C3 C8 119.96(16) . . ? N1 C9 C8 127.79(17) . . ? N1 C9 H9 116.1 . . ? C8 C9 H9 116.1 . . ? C7 C8 C3 119.22(17) . . ? C7 C8 C9 117.39(17) . . ? C3 C8 C9 123.27(16) . . ? C4 C5 C6 121.90(17) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C6 C7 C8 120.63(18) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C10 C15 C14 109.97(17) . . ? C10 C15 H15A 109.7 . . ? C14 C15 H15A 109.7 . . ? C10 C15 H15B 109.7 . . ? C14 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? C10 C11 C12 109.12(16) . . ? C10 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? C10 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? C7 C6 C5 119.90(18) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C10 C17 C16 110.49(16) . . ? C10 C17 H17A 109.6 . . ? C16 C17 H17A 109.6 . . ? C10 C17 H17B 109.6 . . ? C16 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? C18 C16 C19 110.27(19) . . ? C18 C16 C17 109.49(19) . . ? C19 C16 C17 108.54(19) . . ? C18 C16 H16 109.5 . . ? C19 C16 H16 109.5 . . ? C17 C16 H16 109.5 . . ? N1 C10 C17 108.17(14) . . ? N1 C10 C15 108.22(15) . . ? C17 C10 C15 109.68(17) . . ? N1 C10 C11 113.58(15) . . ? C17 C10 C11 108.35(17) . . ? C15 C10 C11 108.79(16) . . ? Al1 C2 H2A 109.5 . . ? Al1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? Al1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C13 C12 C19 109.90(19) . . ? C13 C12 C11 109.23(19) . . ? C19 C12 C11 110.11(19) . . ? C13 C12 H12 109.2 . . ? C19 C12 H12 109.2 . . ? C11 C12 H12 109.2 . . ? C14 C13 C12 109.91(18) . . ? C14 C13 H13A 109.7 . . ? C12 C13 H13A 109.7 . . ? C14 C13 H13B 109.7 . . ? C12 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? C13 C14 C18 109.7(2) . . ? C13 C14 C15 108.92(18) . . ? C18 C14 C15 109.45(18) . . ? C13 C14 H14 109.6 . . ? C18 C14 H14 109.6 . . ? C15 C14 H14 109.6 . . ? C12 C19 C16 108.69(18) . . ? C12 C19 H19A 110.0 . . ? C16 C19 H19A 110.0 . . ? C12 C19 H19B 110.0 . . ? C16 C19 H19B 110.0 . . ? H19A C19 H19B 108.3 . . ? Al1 C1 H1A 109.5 . . ? Al1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Al1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C16 C18 C14 109.83(18) . . ? C16 C18 H18A 109.7 . . ? C14 C18 H18A 109.7 . . ? C16 C18 H18B 109.7 . . ? C14 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.09 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.231 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 906290' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 #TrackingRef '14736_web_deposit_cif_file_4_JingyuLiu_1350442429.2e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H40 Al2 Cl2 N2 O2' _chemical_formula_weight 549.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Al Al 0.0645 0.0514 '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.697(2) _cell_length_b 12.5736(14) _cell_length_c 16.2599(19) _cell_angle_alpha 90.00 _cell_angle_beta 121.377(2) _cell_angle_gamma 90.00 _cell_volume 3089.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.292 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9124 _exptl_absorpt_correction_T_max 0.9466 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8379 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 26.22 _reflns_number_total 3100 _reflns_number_gt 2278 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0418P)^2^+2.7273P] 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 3100 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 Al1 Al 0.24083(4) 0.47765(5) 0.14203(4) 0.03071(17) Uani 1 1 d . . . C2 C 0.15614(15) 0.5855(2) 0.05759(17) 0.0517(6) Uani 1 1 d . . . H2A H 0.1440 0.6348 0.0960 0.078 Uiso 1 1 calc R . . H2B H 0.1010 0.5508 0.0094 0.078 Uiso 1 1 calc R . . H2C H 0.1810 0.6248 0.0251 0.078 Uiso 1 1 calc R . . C1 C 0.23369(17) 0.33202(19) 0.0965(2) 0.0564(7) Uani 1 1 d . . . H1A H 0.2652 0.3271 0.0618 0.085 Uiso 1 1 calc R . . H1B H 0.1715 0.3125 0.0532 0.085 Uiso 1 1 calc R . . H1C H 0.2608 0.2834 0.1517 0.085 Uiso 1 1 calc R . . O1 O 0.35082(8) 0.52368(11) 0.18861(9) 0.0328(3) Uani 1 1 d . . . N1 N 0.24532(10) 0.48324(12) 0.26561(12) 0.0285(4) Uani 1 1 d . . . C10 C 0.17271(13) 0.43845(17) 0.27850(16) 0.0394(5) Uani 1 1 d . . . C13 C 0.14842(16) 0.5155(2) 0.3330(2) 0.0649(8) Uani 1 1 d . . . H13A H 0.1977 0.5209 0.3999 0.097 Uiso 1 1 calc R . . H13B H 0.0956 0.4896 0.3318 0.097 Uiso 1 1 calc R . . H13C H 0.1363 0.5857 0.3025 0.097 Uiso 1 1 calc R . . C12 C 0.09082(16) 0.4216(3) 0.1792(2) 0.0700(9) Uani 1 1 d . . . H12A H 0.0693 0.4904 0.1471 0.105 Uiso 1 1 calc R . . H12B H 0.0446 0.3871 0.1858 0.105 Uiso 1 1 calc R . . H12C H 0.1059 0.3762 0.1407 0.105 Uiso 1 1 calc R . . C11 C 0.2050(2) 0.3334(2) 0.3297(3) 0.0926(12) Uani 1 1 d . . . H11A H 0.2226 0.2876 0.2938 0.139 Uiso 1 1 calc R . . H11B H 0.1575 0.2990 0.3339 0.139 Uiso 1 1 calc R . . H11C H 0.2560 0.3454 0.3947 0.139 Uiso 1 1 calc R . . C9 C 0.31197(12) 0.52645(15) 0.34036(14) 0.0298(4) Uani 1 1 d . . . H9 H 0.3084 0.5302 0.3966 0.036 Uiso 1 1 calc R . . C4 C 0.49000(12) 0.60636(14) 0.28932(14) 0.0261(4) Uani 1 1 d . . . C3 C 0.40854(12) 0.56623(14) 0.27289(14) 0.0256(4) Uani 1 1 d . . . C7 C 0.45346(12) 0.61413(15) 0.43761(14) 0.0314(4) Uani 1 1 d . . . H7 H 0.4409 0.6172 0.4877 0.038 Uiso 1 1 calc R . . C5 C 0.54991(12) 0.64776(15) 0.37940(15) 0.0315(4) Uani 1 1 d . . . H5 H 0.6052 0.6734 0.3911 0.038 Uiso 1 1 calc R . . C8 C 0.39134(12) 0.56974(14) 0.34840(14) 0.0268(4) Uani 1 1 d . . . C6 C 0.53231(13) 0.65322(16) 0.45316(15) 0.0339(5) Uani 1 1 d . . . H6 H 0.5743 0.6836 0.5136 0.041 Uiso 1 1 calc R . . Cl1 Cl 0.51135(7) 0.74701(7) 0.66827(6) 0.0952(3) Uani 1 1 d . . . C14 C 0.5000 0.6710(3) 0.7500 0.0582(10) Uani 1 2 d S . . H14A H 0.5526 0.6246 0.7856 0.070 Uiso 0.50 1 calc PR . . H14B H 0.4474 0.6246 0.7144 0.070 Uiso 0.50 1 calc PR . . 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 0.0256(3) 0.0336(3) 0.0303(3) -0.0074(3) 0.0128(3) -0.0043(3) C2 0.0431(13) 0.0619(15) 0.0403(14) 0.0058(12) 0.0149(11) 0.0077(12) C1 0.0551(15) 0.0471(14) 0.0711(18) -0.0248(13) 0.0357(14) -0.0111(12) O1 0.0279(7) 0.0428(8) 0.0279(7) -0.0098(6) 0.0147(6) -0.0084(6) N1 0.0229(8) 0.0299(8) 0.0325(9) -0.0004(7) 0.0143(7) -0.0029(7) C10 0.0279(10) 0.0457(12) 0.0457(13) 0.0023(10) 0.0199(10) -0.0082(9) C13 0.0462(14) 0.093(2) 0.0743(19) -0.0197(17) 0.0446(15) -0.0174(14) C12 0.0361(14) 0.116(2) 0.0590(17) -0.0228(17) 0.0252(13) -0.0324(15) C11 0.0615(19) 0.0665(19) 0.150(3) 0.047(2) 0.056(2) -0.0048(15) C9 0.0297(10) 0.0324(10) 0.0308(11) -0.0003(9) 0.0182(9) 0.0002(8) C4 0.0250(9) 0.0241(9) 0.0304(11) 0.0009(8) 0.0154(8) 0.0005(7) C3 0.0244(9) 0.0229(9) 0.0286(10) -0.0019(8) 0.0133(8) 0.0018(8) C7 0.0327(10) 0.0356(10) 0.0278(11) -0.0038(9) 0.0170(9) -0.0020(9) C5 0.0261(10) 0.0303(10) 0.0364(12) -0.0018(9) 0.0152(9) -0.0041(8) C8 0.0240(9) 0.0269(9) 0.0292(10) -0.0005(8) 0.0137(8) 0.0002(8) C6 0.0309(10) 0.0372(11) 0.0297(11) -0.0085(9) 0.0131(9) -0.0085(9) Cl1 0.1521(9) 0.0875(6) 0.0660(5) -0.0220(4) 0.0707(6) -0.0415(6) C14 0.062(2) 0.0406(18) 0.078(3) 0.000 0.040(2) 0.000 _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 1.7782(13) . ? Al1 C1 1.954(2) . ? Al1 C2 1.956(2) . ? Al1 N1 1.9706(17) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O1 C3 1.323(2) . ? N1 C9 1.293(2) . ? N1 C10 1.514(2) . ? C10 C11 1.506(3) . ? C10 C13 1.518(3) . ? C10 C12 1.522(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C9 C8 1.448(2) . ? C9 H9 0.9500 . ? C4 C5 1.387(3) . ? C4 C3 1.415(2) . ? C4 C4 1.494(4) 2_655 ? C3 C8 1.411(3) . ? C7 C6 1.373(3) . ? C7 C8 1.401(3) . ? C7 H7 0.9500 . ? C5 C6 1.389(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? Cl1 C14 1.731(2) . ? C14 Cl1 1.731(2) 2_656 ? 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 O1 Al1 C1 107.87(9) . . ? O1 Al1 C2 110.01(9) . . ? C1 Al1 C2 120.57(12) . . ? O1 Al1 N1 95.74(6) . . ? C1 Al1 N1 112.34(10) . . ? C2 Al1 N1 107.47(9) . . ? Al1 C2 H2A 109.5 . . ? Al1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? Al1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? Al1 C1 H1A 109.5 . . ? Al1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Al1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 O1 Al1 131.03(12) . . ? C9 N1 C10 116.80(17) . . ? C9 N1 Al1 120.42(13) . . ? C10 N1 Al1 122.78(13) . . ? C11 C10 N1 107.30(17) . . ? C11 C10 C13 112.2(2) . . ? N1 C10 C13 111.23(17) . . ? C11 C10 C12 110.0(2) . . ? N1 C10 C12 108.24(18) . . ? C13 C10 C12 107.8(2) . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C9 C8 127.62(18) . . ? N1 C9 H9 116.2 . . ? C8 C9 H9 116.2 . . ? C5 C4 C3 118.48(17) . . ? C5 C4 C4 120.82(18) . 2_655 ? C3 C4 C4 120.69(19) . 2_655 ? O1 C3 C8 120.93(16) . . ? O1 C3 C4 120.06(16) . . ? C8 C3 C4 118.98(17) . . ? C6 C7 C8 120.50(18) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C4 C5 C6 122.58(17) . . ? C4 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C7 C8 C3 120.31(16) . . ? C7 C8 C9 116.40(17) . . ? C3 C8 C9 123.27(17) . . ? C7 C6 C5 119.12(18) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? Cl1 C14 Cl1 113.0(2) . 2_656 ? Cl1 C14 H14A 109.0 . . ? Cl1 C14 H14A 109.0 2_656 . ? Cl1 C14 H14B 109.0 . . ? Cl1 C14 H14B 109.0 2_656 . ? H14A C14 H14B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.22 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.285 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 906291'