# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_schu113_compound_1 _database_code_CSD 184045 _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'Schulz, Stephan' ; Institut fur Anorganische Chemie Universitat Bonn Gerhard-Domagk-Str. 1 D-53121 Bonn Bundesrepublik Deutschland ; 'Bauer, Tillmann' ; Institut fur Anorganische Chemie Universitat Bonn Gerhard-Domagk-Str. 1 D-53121 Bonn Bundesrepublik Deutschland ; 'Nieger, Martin' ; Institut fur Anorganische Chemie Universitat Bonn Gerhard-Domagk-Str. 1 D-53121 Bonn Bundesrepublik Deutschland ; 'Krossing, Ingo' ; Institut fur Anorganische Chemie Universitat Karlsruhe Engesserstr. Geb. 30-45 D-76128 Karlsruhe Bundesrepublik Deutschland ; _publ_contact_author_name 'Dr Stephan Schulz' _publ_contact_author_address ; Institut fur Anorganische Chemie Universitat Bonn Gerhard-Domagk-Str. 1 Bonn 53121 GERMANY ; _publ_contact_author_phone '049 228 73-5823' _publ_contact_author_fax '049 228 73-5327' _publ_contact_author_email 'SSCHULZ@UNI-BONN.DE' _publ_requested_journal 'J. Chem. Soc., Chem. Commun.' _publ_requested_coeditor_name ? _publ_contact_letter ; enclosed you will find the necessary data of our publication in J. Chem. Soc., Chem. Commun. ; #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Synthesis and single crystal X-ray structure of the first imido analog of an eigth-membered aluminophosphate heterocycle ; #============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H44 Al2 N4 P2' _chemical_formula_sum 'C16 H44 Al2 N4 P2' _chemical_formula_weight 408.45 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' 'P' 'P' 0.1023 0.0942 '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' _symmetry_Int_Tables_number 14 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 11.5332(6) _cell_length_b 9.4303(5) _cell_length_c 12.2830(8) _cell_angle_alpha 90.00 _cell_angle_beta 109.501(2) _cell_angle_gamma 90.00 _cell_volume 1259.28(12) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2173 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.077 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.249 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 40 mm, 120 sec./deg., 2 deg., 2 sets, 110 frames, mos.= 1.107(5) deg. ; _diffrn_ambient_temperature 123(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 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 5688 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0466 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2221 _reflns_number_gt 1739 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0481P)^2^+0.2081P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2221 _refine_ls_number_parameters 117 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.057 _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 P1 P 0.16860(5) 0.62938(5) 0.56803(4) 0.02321(17) Uani 1 1 d D . . H1P H 0.1736(17) 0.6678(18) 0.4618(13) 0.028 Uiso 1 1 d D . . Al1 Al 0.10002(6) 0.35079(6) 0.42040(5) 0.02243(18) Uani 1 1 d D . . N1 N 0.15014(16) 0.46025(16) 0.55769(14) 0.0242(4) Uani 1 1 d D . . H1N H 0.1481(19) 0.424(2) 0.6182(15) 0.029 Uiso 1 1 d D . . N2 N 0.06282(16) 0.70907(17) 0.60153(15) 0.0271(4) Uani 1 1 d D . . H2N H 0.0807(19) 0.7878(18) 0.6253(18) 0.033 Uiso 1 1 d D . . C1 C 0.32084(19) 0.6842(2) 0.66101(18) 0.0287(5) Uani 1 1 d . . . C2 C 0.3366(2) 0.8430(2) 0.6419(2) 0.0389(6) Uani 1 1 d . . . H2A H 0.2762 0.8973 0.6651 0.058 Uiso 1 1 calc R . . H2B H 0.3237 0.8602 0.5600 0.058 Uiso 1 1 calc R . . H2C H 0.4198 0.8728 0.6884 0.058 Uiso 1 1 calc R . . C3 C 0.4155(2) 0.5987(2) 0.6266(2) 0.0466(7) Uani 1 1 d . . . H3A H 0.4057 0.4977 0.6400 0.070 Uiso 1 1 calc R . . H3B H 0.4985 0.6293 0.6732 0.070 Uiso 1 1 calc R . . H3C H 0.4032 0.6144 0.5447 0.070 Uiso 1 1 calc R . . C4 C 0.3330(2) 0.6564(3) 0.7878(2) 0.0499(7) Uani 1 1 d . . . H4A H 0.2720 0.7132 0.8081 0.075 Uiso 1 1 calc R . . H4B H 0.4158 0.6827 0.8380 0.075 Uiso 1 1 calc R . . H4C H 0.3189 0.5556 0.7982 0.075 Uiso 1 1 calc R . . C5 C 0.0987(2) 0.4756(2) 0.28991(17) 0.0309(5) Uani 1 1 d D . . H5A H 0.0440 0.5576 0.2863 0.037 Uiso 1 1 calc R . . H5B H 0.1827 0.5123 0.3031 0.037 Uiso 1 1 calc R . . C6 C 0.0540(3) 0.3952(2) 0.17459(19) 0.0454(7) Uani 1 1 d D . . H6A H 0.0540 0.4593 0.1118 0.068 Uiso 1 1 calc R . . H6B H -0.0296 0.3599 0.1610 0.068 Uiso 1 1 calc R . . H6C H 0.1091 0.3151 0.1775 0.068 Uiso 1 1 calc R . . C7 C 0.2040(2) 0.1802(2) 0.4362(2) 0.0345(5) Uani 1 1 d D . . H7A H 0.2113 0.1324 0.5100 0.041 Uiso 0.605(8) 1 calc PR A 1 H7B H 0.1630 0.1137 0.3727 0.041 Uiso 0.605(8) 1 calc PR A 1 H7C H 0.1725 0.1071 0.4770 0.041 Uiso 0.395(8) 1 calc PR A 2 H7D H 0.1917 0.1436 0.3576 0.041 Uiso 0.395(8) 1 calc PR A 2 C8 C 0.3336(3) 0.2131(4) 0.4338(4) 0.0429(12) Uiso 0.605(8) 1 d PD A 1 H8A H 0.3806 0.1248 0.4422 0.064 Uiso 0.605(8) 1 calc PR A 1 H8B H 0.3756 0.2775 0.4974 0.064 Uiso 0.605(8) 1 calc PR A 1 H8C H 0.3274 0.2581 0.3601 0.064 Uiso 0.605(8) 1 calc PR A 1 C8' C 0.3370(5) 0.1933(7) 0.4961(7) 0.0429(12) Uiso 0.39 1 d PD A 2 H8'1 H 0.3761 0.1004 0.4987 0.064 Uiso 0.395(8) 1 calc PR A 2 H8'2 H 0.3521 0.2274 0.5750 0.064 Uiso 0.395(8) 1 calc PR A 2 H8'3 H 0.3717 0.2607 0.4546 0.064 Uiso 0.395(8) 1 calc PR A 2 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 P1 0.0240(3) 0.0223(3) 0.0215(3) -0.0005(2) 0.0051(2) -0.0007(2) Al1 0.0251(4) 0.0194(3) 0.0234(4) -0.0001(2) 0.0089(3) 0.0005(2) N1 0.0297(10) 0.0226(9) 0.0201(10) 0.0034(7) 0.0083(8) -0.0006(7) N2 0.0278(10) 0.0187(9) 0.0350(10) -0.0079(7) 0.0107(8) -0.0039(8) C1 0.0246(12) 0.0293(11) 0.0286(12) -0.0009(9) 0.0042(9) -0.0034(9) C2 0.0368(14) 0.0333(12) 0.0454(15) -0.0055(10) 0.0120(12) -0.0094(10) C3 0.0246(13) 0.0428(14) 0.0678(19) -0.0058(12) 0.0093(12) 0.0003(11) C4 0.0470(16) 0.0599(16) 0.0293(14) 0.0050(11) -0.0053(12) -0.0123(13) C5 0.0421(14) 0.0268(11) 0.0253(12) -0.0029(8) 0.0134(11) -0.0029(10) C6 0.077(2) 0.0344(13) 0.0262(13) -0.0041(10) 0.0192(13) -0.0040(13) C7 0.0328(13) 0.0290(11) 0.0440(14) -0.0022(10) 0.0160(11) 0.0001(10) _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 P1 N2 1.5993(17) . ? P1 N1 1.6085(16) . ? P1 C1 1.821(2) . ? P1 H1P 1.374(14) . ? Al1 N2 1.8922(18) 3_566 ? Al1 N1 1.8954(17) . ? Al1 C7 1.977(2) . ? Al1 C5 1.985(2) . ? N1 H1N 0.826(15) . ? N2 Al1 1.8922(18) 3_566 ? N2 H2N 0.799(15) . ? C1 C3 1.526(3) . ? C1 C2 1.536(3) . ? C1 C4 1.539(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.536(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8' 1.469(6) . ? C7 C8 1.537(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 H7C 0.9900 . ? C7 H7D 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C8' H8'1 0.9800 . ? C8' H8'2 0.9800 . ? C8' H8'3 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 N2 P1 N1 113.21(9) . . ? N2 P1 C1 111.34(9) . . ? N1 P1 C1 113.91(9) . . ? N2 P1 H1P 113.5(8) . . ? N1 P1 H1P 103.5(7) . . ? C1 P1 H1P 100.6(8) . . ? N2 Al1 N1 106.42(8) 3_566 . ? N2 Al1 C7 108.17(8) 3_566 . ? N1 Al1 C7 111.15(9) . . ? N2 Al1 C5 108.81(9) 3_566 . ? N1 Al1 C5 108.26(8) . . ? C7 Al1 C5 113.76(9) . . ? P1 N1 Al1 127.11(10) . . ? P1 N1 H1N 112.6(15) . . ? Al1 N1 H1N 118.9(15) . . ? P1 N2 Al1 129.00(10) . 3_566 ? P1 N2 H2N 113.9(15) . . ? Al1 N2 H2N 116.9(15) 3_566 . ? C3 C1 C2 109.91(18) . . ? C3 C1 C4 111.02(19) . . ? C2 C1 C4 110.18(18) . . ? C3 C1 P1 107.82(15) . . ? C2 C1 P1 108.61(15) . . ? C4 C1 P1 109.23(15) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 Al1 111.21(14) . . ? C6 C5 H5A 109.4 . . ? Al1 C5 H5A 109.4 . . ? C6 C5 H5B 109.4 . . ? Al1 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8' C7 C8 29.8(3) . . ? C8' C7 Al1 118.6(3) . . ? C8 C7 Al1 113.31(19) . . ? C8' C7 H7A 79.9 . . ? C8 C7 H7A 108.9 . . ? Al1 C7 H7A 108.9 . . ? C8' C7 H7B 126.3 . . ? C8 C7 H7B 108.9 . . ? Al1 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C8' C7 H7C 107.7 . . ? C8 C7 H7C 132.4 . . ? Al1 C7 H7C 107.7 . . ? H7A C7 H7C 32.1 . . ? H7B C7 H7C 78.4 . . ? C8' C7 H7D 107.7 . . ? C8 C7 H7D 82.8 . . ? Al1 C7 H7D 107.7 . . ? H7A C7 H7D 132.4 . . ? H7B C7 H7D 30.1 . . ? H7C C7 H7D 107.1 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C8' H8'1 109.5 . . ? C7 C8' H8'2 109.5 . . ? H8'1 C8' H8'2 109.5 . . ? C7 C8' H8'3 109.5 . . ? H8'1 C8' H8'3 109.5 . . ? H8'2 C8' H8'3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 P1 N1 Al1 107.04(13) . . . . ? C1 P1 N1 Al1 -124.40(12) . . . . ? N2 Al1 N1 P1 -107.93(13) 3_566 . . . ? C7 Al1 N1 P1 134.52(13) . . . . ? C5 Al1 N1 P1 8.89(16) . . . . ? N1 P1 N2 Al1 -23.72(16) . . . 3_566 ? C1 P1 N2 Al1 -153.59(12) . . . 3_566 ? N2 P1 C1 C3 177.58(14) . . . . ? N1 P1 C1 C3 48.09(18) . . . . ? N2 P1 C1 C2 -63.35(17) . . . . ? N1 P1 C1 C2 167.15(14) . . . . ? N2 P1 C1 C4 56.84(17) . . . . ? N1 P1 C1 C4 -72.65(17) . . . . ? N2 Al1 C5 C6 -62.55(18) 3_566 . . . ? N1 Al1 C5 C6 -177.82(16) . . . . ? C7 Al1 C5 C6 58.10(19) . . . . ? N2 Al1 C7 C8' -157.1(4) 3_566 . . . ? N1 Al1 C7 C8' -40.6(4) . . . . ? C5 Al1 C7 C8' 81.9(4) . . . . ? N2 Al1 C7 C8 170.1(2) 3_566 . . . ? N1 Al1 C7 C8 -73.4(2) . . . . ? C5 Al1 C7 C8 49.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.413 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.052 #============================================================================== # End of Crystallographic Information File