# 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_2 #TrackingRef '19114_web_deposit_cif_file_0_YingPeng_1364894547.2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H19 Al N2' _chemical_formula_weight 182.24 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' N N 0.0061 0.0033 '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 Orthorhombic _symmetry_space_group_name_H-M 'Pmmn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z' 'x+1/2, -y, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z' '-x-1/2, y, z' _cell_length_a 9.126(7) _cell_length_b 7.598(6) _cell_length_c 8.267(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 573.2(8) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1088 _cell_measurement_theta_min 2.464 _cell_measurement_theta_max 22.724 _exptl_crystal_description block _exptl_crystal_colour 'transparent white' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.056 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 200 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9648 _exptl_absorpt_correction_T_max 0.9789 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3094 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_unetI/netI 0.0190 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 24.99 _reflns_number_total 581 _reflns_number_gt 537 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0152P)^2^+0.3896P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'riding mode' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.121(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 581 _refine_ls_number_parameters 54 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.2500 0.2500 0.69705(12) 0.0453(4) Uani 1 4 d S . . N1 N 0.4039(2) 0.2500 0.8506(2) 0.0480(5) Uani 1 2 d S . . C2 C 0.3868(3) 0.2500 1.0089(3) 0.0508(7) Uani 1 2 d S . . C3 C 0.2500 0.2500 1.0823(4) 0.0583(10) Uani 1 4 d S . . H3A H 0.2500 0.2500 1.1948 0.070 Uiso 1 4 calc SR . . C5 C 0.5198(5) 0.2500 1.1179(6) 0.0870(12) Uani 1 2 d S . . C4 C 0.5526(4) 0.2500 0.7829(6) 0.0816(11) Uani 1 2 d S . . C1 C 0.2500 0.0335(4) 0.5673(3) 0.0747(9) Uani 1 2 d S . . H1A H 0.2500 -0.0669 0.6378 0.112 Uiso 1 2 d SR . . H1B H 0.1641 0.0309 0.5003 0.112 Uiso 1 1 d R . . H5A H 0.489(5) 0.2500 1.223(5) 0.135(18) Uiso 1 2 d S . . H5B H 0.584(2) 0.357(3) 1.095(3) 0.104(8) Uiso 1 1 d . . . H4A H 0.604(2) 0.145(3) 0.814(3) 0.115(9) Uiso 1 1 d . . . H4B H 0.545(4) 0.2500 0.668(5) 0.129(17) Uiso 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 Al1 0.0493(6) 0.0468(6) 0.0399(6) 0.000 0.000 0.000 N1 0.0348(10) 0.0503(12) 0.0590(12) 0.000 0.0010(9) 0.000 C2 0.0548(15) 0.0398(13) 0.0579(15) 0.000 -0.0172(13) 0.000 C3 0.077(3) 0.059(2) 0.0392(18) 0.000 0.000 0.000 C5 0.084(3) 0.077(2) 0.100(3) 0.000 -0.051(2) 0.000 C4 0.0411(16) 0.091(3) 0.112(3) 0.000 0.0143(18) 0.000 C1 0.100(2) 0.0666(19) 0.0576(16) -0.0135(15) 0.000 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 N1 1.893(2) . ? Al1 N1 1.893(2) 2 ? Al1 C1 1.964(3) . ? Al1 C1 1.964(3) 2 ? N1 C2 1.318(3) . ? N1 C4 1.468(4) . ? C2 C3 1.388(3) . ? C2 C5 1.511(4) . ? C3 C2 1.388(3) 2 ? 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 N1 Al1 N1 95.76(14) . 2 ? N1 Al1 C1 111.49(6) . . ? N1 Al1 C1 111.49(6) 2 . ? N1 Al1 C1 111.49(6) . 2 ? N1 Al1 C1 111.49(6) 2 2 ? C1 Al1 C1 113.79(19) . 2 ? C2 N1 C4 119.2(3) . . ? C2 N1 Al1 125.33(18) . . ? C4 N1 Al1 115.5(2) . . ? N1 C2 C3 122.7(2) . . ? N1 C2 C5 119.8(3) . . ? C3 C2 C5 117.5(3) . . ? C2 C3 C2 128.2(3) 2 . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.212 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 922212' ####################################################################### # # 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_p #TrackingRef '19115_web_deposit_cif_file_0_YingPeng_1364894830.2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H31 Al N2 O0' _chemical_formula_weight 266.40 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 Orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 17.867(3) _cell_length_b 23.885(4) _cell_length_c 8.1825(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3491.9(9) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2024 _cell_measurement_theta_min 2.848 _cell_measurement_theta_max 24.896 _exptl_crystal_description block _exptl_crystal_colour 'transparent white' _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.013 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9395 _exptl_absorpt_correction_T_max 0.9813 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4727 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_unetI/netI 0.0196 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1506 _reflns_number_gt 1416 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0742P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(3) _refine_ls_number_reflns 1506 _refine_ls_number_parameters 88 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.1009 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.501 _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 0.0000 0.0000 0.16987(10) 0.0453(3) Uani 1 2 d S . . N1 N -0.07218(11) -0.03212(8) 0.0210(3) 0.0495(5) Uani 1 1 d . . . C1 C -0.04723(19) 0.06214(13) 0.2935(4) 0.0712(8) Uani 1 1 d . . . H1A H -0.0963 0.0692 0.2504 0.107 Uiso 1 1 calc R . . H1B H -0.0171 0.0953 0.2831 0.107 Uiso 1 1 calc R . . H1C H -0.0511 0.0520 0.4067 0.107 Uiso 1 1 calc R . . C2 C -0.06074(14) -0.02918(11) -0.1387(3) 0.0519(6) Uani 1 1 d . . . C3 C -0.1082(2) -0.0558(2) -0.2703(5) 0.0949(12) Uani 1 1 d . . . H3A H -0.1527 -0.0712 -0.2222 0.142 Uiso 1 1 calc R . . H3B H -0.0803 -0.0852 -0.3224 0.142 Uiso 1 1 calc R . . H3C H -0.1217 -0.0281 -0.3499 0.142 Uiso 1 1 calc R . . C4 C 0.0000 0.0000 -0.2077(4) 0.0518(8) Uani 1 2 d S . . H4A H 0.0000 0.0000 -0.3214 0.062 Uiso 1 2 calc SR . . C5 C -0.13966(17) -0.06231(15) 0.0881(5) 0.0754(9) Uani 1 1 d . . . C6 C -0.21220(19) -0.0360(3) 0.0272(10) 0.146(3) Uani 1 1 d . . . H6A H -0.2016 -0.0001 -0.0203 0.219 Uiso 1 1 calc R . . H6B H -0.2461 -0.0314 0.1172 0.219 Uiso 1 1 calc R . . H6C H -0.2345 -0.0598 -0.0536 0.219 Uiso 1 1 calc R . . C7 C -0.1418(2) -0.0549(2) 0.2732(6) 0.1043(14) Uani 1 1 d . . . H7A H -0.1492 -0.0161 0.2990 0.156 Uiso 1 1 calc R . . H7B H -0.0954 -0.0674 0.3194 0.156 Uiso 1 1 calc R . . H7C H -0.1822 -0.0766 0.3177 0.156 Uiso 1 1 calc R . . C8 C -0.1325(3) -0.12572(16) 0.0609(9) 0.1214(18) Uani 1 1 d . . . H8A H -0.0878 -0.1391 0.1130 0.182 Uiso 1 1 calc R . . H8B H -0.1300 -0.1334 -0.0541 0.182 Uiso 1 1 calc R . . H8C H -0.1752 -0.1443 0.1069 0.182 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 0.0616(5) 0.0417(5) 0.0325(5) 0.000 0.000 0.0061(4) N1 0.0549(11) 0.0464(11) 0.0470(12) 0.0022(9) 0.0009(9) -0.0012(8) C1 0.102(2) 0.0611(15) 0.0505(16) -0.0066(14) 0.0082(16) 0.0190(16) C2 0.0607(13) 0.0505(15) 0.0444(14) -0.0050(10) -0.0114(11) 0.0054(12) C3 0.104(3) 0.108(3) 0.073(2) -0.0156(19) -0.030(2) -0.018(2) C4 0.073(2) 0.052(2) 0.0303(17) 0.000 0.000 0.0083(15) C5 0.0615(16) 0.080(2) 0.085(2) 0.0098(18) 0.0068(15) -0.0187(14) C6 0.059(2) 0.213(7) 0.165(5) 0.068(5) 0.015(3) 0.003(3) C7 0.104(3) 0.121(3) 0.088(3) 0.017(3) 0.041(2) -0.024(2) C8 0.133(3) 0.076(2) 0.155(5) -0.002(3) 0.020(4) -0.045(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 N1 1.933(2) . ? Al1 N1 1.933(2) 2 ? Al1 C1 1.984(3) 2 ? Al1 C1 1.984(3) . ? N1 C2 1.324(3) . ? N1 C5 1.508(4) . ? C2 C4 1.408(3) . ? C2 C3 1.511(4) . ? C4 C2 1.408(3) 2 ? C5 C7 1.526(6) . ? C5 C8 1.536(6) . ? C5 C6 1.525(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Al1 N1 101.84(13) . 2 ? N1 Al1 C1 107.95(12) . 2 ? N1 Al1 C1 109.53(12) 2 2 ? N1 Al1 C1 109.53(12) . . ? N1 Al1 C1 107.95(12) 2 . ? C1 Al1 C1 118.7(2) 2 . ? C2 N1 C5 120.5(3) . . ? C2 N1 Al1 119.87(17) . . ? C5 N1 Al1 119.6(2) . . ? N1 C2 C4 122.7(2) . . ? N1 C2 C3 126.4(3) . . ? C4 C2 C3 110.8(3) . . ? C2 C4 C2 132.7(3) 2 . ? N1 C5 C7 109.1(3) . . ? N1 C5 C8 110.6(3) . . ? C7 C5 C8 105.0(4) . . ? N1 C5 C6 111.3(3) . . ? C7 C5 C6 104.8(4) . . ? C8 C5 C6 115.5(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.131 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.032 _database_code_depnum_ccdc_archive 'CCDC 922213' ####################################################################### # # 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_0 #TrackingRef '19116_web_deposit_cif_file_0_YingPeng_1364895127.2h.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H43 Al N2' _chemical_formula_weight 350.55 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' Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.8557(5) _cell_length_b 25.6952(13) _cell_length_c 9.2957(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.639(3) _cell_angle_gamma 90.00 _cell_volume 2297.04(19) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4192 _cell_measurement_theta_min 2.381 _cell_measurement_theta_max 22.583 _exptl_crystal_description block _exptl_crystal_colour 'transparent white' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.014 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9707 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14693 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_unetI/netI 0.0299 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4031 _reflns_number_gt 3143 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0793P)^2^+0.5982P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'riding mode' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4031 _refine_ls_number_parameters 220 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1435 _refine_ls_wR_factor_gt 0.1348 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.082 _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 0.71835(6) 0.35858(2) 0.81794(6) 0.0388(2) Uani 1 1 d . . . N1 N 0.62645(17) 0.38471(6) 0.96910(17) 0.0418(4) Uani 1 1 d . . . N2 N 0.82597(16) 0.41865(6) 0.77909(17) 0.0402(4) Uani 1 1 d . . . C1 C 0.6101(3) 0.45642(11) 1.1516(3) 0.0666(7) Uani 1 1 d . . . H1A H 0.5552 0.4316 1.1911 0.100 Uiso 1 1 calc R . . H1B H 0.5554 0.4869 1.1199 0.100 Uiso 1 1 calc R . . H1C H 0.6901 0.4658 1.2262 0.100 Uiso 1 1 calc R . . C2 C 0.6572(2) 0.43247(8) 1.0207(2) 0.0445(5) Uani 1 1 d . . . C3 C 0.7376(2) 0.46761(8) 0.9590(2) 0.0465(5) Uani 1 1 d . . . H3A H 0.7434 0.5005 1.0015 0.056 Uiso 1 1 calc R . . C4 C 0.8109(2) 0.46310(8) 0.8466(2) 0.0435(5) Uani 1 1 d . . . C5 C 0.8689(3) 0.51553(9) 0.8116(3) 0.0690(7) Uani 1 1 d . . . H5A H 0.8972 0.5133 0.7193 0.104 Uiso 1 1 calc R . . H5B H 0.9476 0.5245 0.8884 0.104 Uiso 1 1 calc R . . H5C H 0.7985 0.5418 0.8051 0.104 Uiso 1 1 calc R . . C6 C 0.5321(2) 0.34936(9) 1.0340(2) 0.0543(6) Uani 1 1 d . . . C7 C 0.4980(3) 0.30084(10) 0.9379(3) 0.0685(7) Uani 1 1 d . . . H7A H 0.4511 0.3109 0.8401 0.103 Uiso 1 1 calc R . . H7B H 0.4389 0.2783 0.9793 0.103 Uiso 1 1 calc R . . H7C H 0.5825 0.2829 0.9338 0.103 Uiso 1 1 calc R . . C8 C 0.6060(3) 0.32999(12) 1.1883(3) 0.0786(8) Uani 1 1 d . . . H8A H 0.6926 0.3139 1.1828 0.118 Uiso 1 1 calc R . . H8B H 0.5480 0.3051 1.2232 0.118 Uiso 1 1 calc R . . H8C H 0.6235 0.3589 1.2552 0.118 Uiso 1 1 calc R . . C9 C 0.3911(3) 0.37530(12) 1.0335(3) 0.0763(8) Uani 1 1 d . . . H9A H 0.3733 0.4019 0.9592 0.114 Uiso 1 1 calc R . . H9B H 0.3935 0.3906 1.1283 0.114 Uiso 1 1 calc R . . H9C H 0.3187 0.3496 1.0127 0.114 Uiso 1 1 calc R . . C10 C 0.9141(2) 0.41545(9) 0.6646(2) 0.0497(5) Uani 1 1 d . . . C11 C 1.0644(2) 0.43296(11) 0.7271(3) 0.0681(7) Uani 1 1 d . . . H11A H 1.0964 0.4186 0.8239 0.102 Uiso 1 1 calc R . . H11B H 1.0679 0.4703 0.7327 0.102 Uiso 1 1 calc R . . H11C H 1.1229 0.4210 0.6638 0.102 Uiso 1 1 calc R . . C12 C 0.8461(3) 0.44489(12) 0.5228(3) 0.0731(8) Uani 1 1 d . . . H12A H 0.8371 0.4810 0.5452 0.110 Uiso 1 1 calc R . . H12B H 0.7557 0.4305 0.4832 0.110 Uiso 1 1 calc R . . H12C H 0.9030 0.4415 0.4517 0.110 Uiso 1 1 calc R . . C13 C 0.9242(3) 0.35855(10) 0.6197(3) 0.0684(7) Uani 1 1 d . . . H13A H 0.9681 0.3385 0.7043 0.103 Uiso 1 1 calc R . . H13B H 0.9782 0.3563 0.5456 0.103 Uiso 1 1 calc R . . H13C H 0.8325 0.3451 0.5811 0.103 Uiso 1 1 calc R . . C14 C 0.5735(2) 0.34520(9) 0.6347(2) 0.0505(5) Uani 1 1 d . . . H14A H 0.6165 0.3502 0.5514 0.061 Uiso 1 1 calc R . . H14B H 0.5476 0.3088 0.6351 0.061 Uiso 1 1 calc R . . C15 C 0.4385(2) 0.37747(9) 0.6061(2) 0.0529(6) Uani 1 1 d . . . H15A H 0.4014 0.3756 0.6956 0.063 Uiso 1 1 calc R . . C16 C 0.3277(3) 0.35573(14) 0.4804(3) 0.0880(9) Uani 1 1 d . . . H16A H 0.2456 0.3769 0.4673 0.132 Uiso 1 1 calc R . . H16B H 0.3057 0.3207 0.5032 0.132 Uiso 1 1 calc R . . H16C H 0.3619 0.3559 0.3913 0.132 Uiso 1 1 calc R . . C17 C 0.4638(3) 0.43385(11) 0.5789(4) 0.0805(8) Uani 1 1 d . . . H17A H 0.3774 0.4525 0.5633 0.121 Uiso 1 1 calc R . . H17B H 0.5026 0.4370 0.4932 0.121 Uiso 1 1 calc R . . H17C H 0.5274 0.4481 0.6629 0.121 Uiso 1 1 calc R . . C18 C 0.8479(2) 0.30192(8) 0.9096(3) 0.0532(6) Uani 1 1 d . . . H18A H 0.8006 0.2815 0.9715 0.064 Uiso 1 1 calc R . . H18B H 0.8626 0.2793 0.8309 0.064 Uiso 1 1 calc R . . C19 C 0.9915(2) 0.31669(9) 1.0028(3) 0.0613(7) Uani 1 1 d . . . H19A H 1.0365 0.3392 0.9419 0.074 Uiso 1 1 calc R . . C20 C 0.9821(3) 0.34702(13) 1.1388(4) 0.0914(10) Uani 1 1 d . . . H20A H 1.0739 0.3556 1.1928 0.137 Uiso 1 1 calc R . . H20B H 0.9360 0.3263 1.1998 0.137 Uiso 1 1 calc R . . H20C H 0.9302 0.3784 1.1107 0.137 Uiso 1 1 calc R . . C21 C 1.0844(3) 0.26949(12) 1.0449(4) 0.0973(11) Uani 1 1 d . . . H21A H 1.0905 0.2505 0.9576 0.146 Uiso 1 1 calc R . . H21B H 1.0458 0.2474 1.1091 0.146 Uiso 1 1 calc R . . H21C H 1.1756 0.2807 1.0946 0.146 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 0.0396(4) 0.0340(3) 0.0423(3) -0.0011(2) 0.0078(3) -0.0007(2) N1 0.0400(9) 0.0459(10) 0.0391(9) 0.0048(7) 0.0077(7) 0.0011(8) N2 0.0382(9) 0.0392(9) 0.0428(9) 0.0028(7) 0.0081(7) 0.0001(7) C1 0.0749(17) 0.0776(17) 0.0482(13) -0.0110(12) 0.0158(12) 0.0134(14) C2 0.0410(12) 0.0527(13) 0.0366(10) -0.0018(9) 0.0017(9) 0.0094(9) C3 0.0476(12) 0.0370(11) 0.0515(12) -0.0103(9) 0.0040(10) 0.0015(9) C4 0.0375(11) 0.0373(11) 0.0508(12) 0.0021(9) -0.0009(9) -0.0024(9) C5 0.0732(17) 0.0434(13) 0.0910(18) 0.0047(13) 0.0190(15) -0.0114(12) C6 0.0505(13) 0.0607(14) 0.0542(13) 0.0145(11) 0.0172(11) -0.0011(11) C7 0.0620(16) 0.0614(15) 0.0837(17) 0.0174(13) 0.0193(14) -0.0148(13) C8 0.084(2) 0.093(2) 0.0616(15) 0.0308(15) 0.0221(14) 0.0046(16) C9 0.0546(16) 0.086(2) 0.095(2) 0.0159(16) 0.0319(15) 0.0033(14) C10 0.0443(12) 0.0568(13) 0.0502(12) 0.0075(10) 0.0151(10) 0.0001(10) C11 0.0447(14) 0.0839(19) 0.0786(17) 0.0054(14) 0.0198(12) -0.0029(12) C12 0.0715(17) 0.096(2) 0.0536(14) 0.0184(14) 0.0182(13) 0.0026(15) C13 0.0727(17) 0.0705(17) 0.0723(16) -0.0112(13) 0.0384(14) 0.0020(13) C14 0.0521(13) 0.0480(12) 0.0502(12) -0.0102(10) 0.0085(10) -0.0048(10) C15 0.0480(13) 0.0647(15) 0.0438(11) -0.0008(10) 0.0053(10) -0.0012(11) C16 0.0572(17) 0.107(2) 0.088(2) -0.0162(17) -0.0092(15) -0.0081(16) C17 0.0629(17) 0.0679(18) 0.102(2) 0.0051(15) -0.0021(15) 0.0102(14) C18 0.0498(13) 0.0387(11) 0.0714(14) 0.0040(10) 0.0138(11) 0.0011(10) C19 0.0459(13) 0.0508(14) 0.0824(17) 0.0223(12) 0.0036(12) 0.0016(10) C20 0.0695(19) 0.087(2) 0.100(2) -0.0071(18) -0.0191(17) 0.0022(16) C21 0.0629(18) 0.0713(19) 0.149(3) 0.0274(19) 0.0039(19) 0.0211(15) _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 N1 1.9499(17) . ? Al1 N2 1.9508(17) . ? Al1 C14 1.998(2) . ? Al1 C18 2.000(2) . ? N1 C2 1.328(3) . ? N1 C6 1.517(3) . ? N2 C4 1.327(3) . ? N2 C10 1.516(3) . ? C1 C2 1.523(3) . ? C2 C3 1.404(3) . ? C3 C4 1.399(3) . ? C4 C5 1.526(3) . ? C6 C7 1.528(4) . ? C6 C9 1.540(3) . ? C6 C8 1.543(3) . ? C10 C13 1.529(3) . ? C10 C11 1.536(3) . ? C10 C12 1.540(3) . ? C14 C15 1.540(3) . ? C15 C17 1.501(4) . ? C15 C16 1.521(3) . ? C18 C19 1.537(3) . ? C19 C20 1.506(4) . ? C19 C21 1.518(3) . ? 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 N1 Al1 N2 102.59(7) . . ? N1 Al1 C14 108.38(8) . . ? N2 Al1 C14 107.13(9) . . ? N1 Al1 C18 107.31(9) . . ? N2 Al1 C18 109.43(8) . . ? C14 Al1 C18 120.55(10) . . ? C2 N1 C6 121.39(17) . . ? C2 N1 Al1 118.25(13) . . ? C6 N1 Al1 120.16(14) . . ? C4 N2 C10 121.29(17) . . ? C4 N2 Al1 118.15(13) . . ? C10 N2 Al1 120.34(13) . . ? N1 C2 C3 123.44(18) . . ? N1 C2 C1 125.2(2) . . ? C3 C2 C1 111.4(2) . . ? C4 C3 C2 132.97(19) . . ? N2 C4 C3 123.64(18) . . ? N2 C4 C5 125.0(2) . . ? C3 C4 C5 111.40(19) . . ? N1 C6 C7 109.37(18) . . ? N1 C6 C9 111.76(19) . . ? C7 C6 C9 105.6(2) . . ? N1 C6 C8 110.9(2) . . ? C7 C6 C8 106.2(2) . . ? C9 C6 C8 112.6(2) . . ? N2 C10 C13 108.94(17) . . ? N2 C10 C11 111.81(18) . . ? C13 C10 C11 105.6(2) . . ? N2 C10 C12 111.41(18) . . ? C13 C10 C12 106.2(2) . . ? C11 C10 C12 112.5(2) . . ? C15 C14 Al1 118.92(14) . . ? C17 C15 C16 110.0(2) . . ? C17 C15 C14 112.3(2) . . ? C16 C15 C14 112.5(2) . . ? C19 C18 Al1 118.94(15) . . ? C20 C19 C21 110.0(3) . . ? C20 C19 C18 112.5(2) . . ? C21 C19 C18 112.2(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.228 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 922214'