# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Alajos Kalman' 'Gyula Argay' 'Gabor Bernath' 'Laszlo Fabian' 'Zsuzsanna Cs. Gyarmati' _publ_contact_author_name 'Prof Alajos Kalman' _publ_contact_author_address ; Institute of Structural Chemsitry Chemical Research Center Pusztaszeri 59-67 Budapest 1025 HUNGARY ; _publ_contact_author_email AKALMAN@CHEMRES.HU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Two polymorphs of a (beta)-lactam (trans-13-azabicyclo [10.2.0] tetradecan-14-one) hallmarked by isostructurality ; data_formI _database_code_depnum_ccdc_archive 'CCDC 241104' _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-13-azabicyclo[12.2.0]tetradecan-14-one ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H23 N O' _chemical_formula_sum 'C13 H23 N O' _chemical_formula_weight 209.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 5.858(1) _cell_length_b 7.629(1) _cell_length_c 28.237(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.97(1) _cell_angle_gamma 90.00 _cell_volume 1249.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 25.16 _cell_measurement_theta_max 29.02 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.113 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.532 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.845 _exptl_absorpt_correction_T_max 0.953 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'CU k\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_reflns_number 3008 _diffrn_reflns_av_R_equivalents 0.0113 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 75.59 _reflns_number_total 2599 _reflns_number_gt 1707 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express' _computing_cell_refinement 'CAD4 Express' _computing_data_reduction 'XCAD4 (Harms 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0614P)^2^+0.0284P] 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 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2599 _refine_ls_number_parameters 159 _refine_ls_number_restraints 186 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.065 _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 O1 O 1.03592(18) 0.40059(13) 0.26031(3) 0.0563(3) Uani 1 1 d U . . N13 N 0.8380(2) 0.56870(15) 0.19905(4) 0.0534(3) Uani 1 1 d U . . H13 H 0.8760 0.6769 0.2036 0.040(4) Uiso 1 1 d R . . C1 C 0.7441(2) 0.30632(16) 0.18952(4) 0.0405(3) Uani 1 1 d U . . H1 H 0.8270 0.2236 0.1715 0.051(4) Uiso 1 1 d R . . C2 C 0.5594(2) 0.21930(18) 0.21417(4) 0.0438(3) Uani 1 1 d U . . H2A H 0.6311 0.1295 0.2356 0.058(4) Uiso 1 1 d R . . H2B H 0.4946 0.3063 0.2336 0.056(4) Uiso 1 1 d R . . C3 C 0.3641(2) 0.13615(18) 0.18043(5) 0.0455(3) Uani 1 1 d U . . H3A H 0.3021 0.2235 0.1572 0.051(4) Uiso 1 1 d R . . H3B H 0.2422 0.1040 0.1988 0.058(4) Uiso 1 1 d R . . C4 C 0.4283(3) -0.02463(19) 0.15363(5) 0.0525(4) Uani 1 1 d U . . H4A H 0.5508 0.0062 0.1353 0.050(4) Uiso 1 1 d R . . H4B H 0.4876 -0.1137 0.1766 0.071(5) Uiso 1 1 d R . . C5 C 0.2264(3) -0.1007(2) 0.11991(6) 0.0654(4) Uani 1 1 d U . . H5A H 0.1053 -0.1328 0.1385 0.090(6) Uiso 1 1 d R . . H5B H 0.2772 -0.2070 0.1057 0.078(5) Uiso 1 1 d R . . C6 C 0.1262(3) 0.0230(2) 0.07990(6) 0.0641(4) Uani 1 1 d U . . H6A H -0.0156 -0.0274 0.0637 0.077(5) Uiso 1 1 d R . . H6B H 0.0872 0.1330 0.0941 0.060(4) Uiso 1 1 d R . . C7 C 0.2854(3) 0.0615(2) 0.04279(5) 0.0645(4) Uani 1 1 d U . . H7A H 0.4428 0.0378 0.0570 0.057(4) Uiso 1 1 d R . . H7B H 0.2482 -0.0185 0.0162 0.076(5) Uiso 1 1 d R . . C8 C 0.2736(3) 0.2485(3) 0.02361(5) 0.0681(5) Uani 1 1 d U . . H8A H 0.1133 0.2771 0.0129 0.077(5) Uiso 1 1 d R . . H8B H 0.3545 0.2534 -0.0041 0.083(5) Uiso 1 1 d R . . C9 C 0.3744(3) 0.3881(2) 0.05945(5) 0.0606(4) Uani 1 1 d U . . H9A H 0.2971 0.3812 0.0877 0.067(5) Uiso 1 1 d R . . H9B H 0.3431 0.5029 0.0454 0.069(5) Uiso 1 1 d R . . C10 C 0.6316(3) 0.3704(2) 0.07460(5) 0.0600(4) Uani 1 1 d U . . H10A H 0.6617 0.2529 0.0871 0.066(5) Uiso 1 1 d R . . H10B H 0.7074 0.3812 0.0463 0.082(5) Uiso 1 1 d R . . C11 C 0.7435(3) 0.5003(2) 0.11188(5) 0.0575(4) Uani 1 1 d U . . H11A H 0.7039 0.6181 0.1007 0.071(5) Uiso 1 1 d R . . H11B H 0.9095 0.4885 0.1141 0.071(5) Uiso 1 1 d R . . C12 C 0.6771(2) 0.47998(17) 0.16166(5) 0.0447(3) Uani 1 1 d U . . H12 H 0.5164 0.5132 0.1629 0.044(4) Uiso 1 1 d R . . C14 C 0.9040(2) 0.42261(16) 0.22320(5) 0.0434(3) Uani 1 1 d U . . 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 O1 0.0565(6) 0.0441(5) 0.0623(6) 0.0003(5) -0.0133(5) 0.0007(5) N13 0.0649(8) 0.0341(5) 0.0567(7) -0.0010(5) -0.0070(6) -0.0030(5) C1 0.0414(7) 0.0352(6) 0.0444(6) -0.0034(5) 0.0039(5) 0.0031(6) C2 0.0468(7) 0.0434(7) 0.0407(6) 0.0014(6) 0.0044(6) 0.0009(6) C3 0.0422(7) 0.0481(7) 0.0457(7) 0.0013(6) 0.0045(6) -0.0027(6) C4 0.0574(9) 0.0469(8) 0.0506(8) -0.0003(6) -0.0019(7) -0.0009(7) C5 0.0709(11) 0.0583(10) 0.0643(9) -0.0084(8) -0.0009(8) -0.0135(8) C6 0.0560(9) 0.0756(11) 0.0564(9) -0.0116(8) -0.0069(7) -0.0076(8) C7 0.0704(11) 0.0736(10) 0.0472(8) -0.0162(8) -0.0002(8) -0.0008(9) C8 0.0751(11) 0.0833(12) 0.0429(7) -0.0027(8) -0.0027(7) 0.0012(10) C9 0.0697(10) 0.0640(10) 0.0463(8) 0.0029(7) 0.0012(7) 0.0041(8) C10 0.0648(10) 0.0707(10) 0.0453(7) 0.0000(8) 0.0108(7) -0.0004(8) C11 0.0601(9) 0.0602(9) 0.0522(8) 0.0062(7) 0.0076(7) -0.0078(8) C12 0.0478(8) 0.0396(7) 0.0453(7) -0.0005(6) 0.0013(6) 0.0008(6) C14 0.0416(7) 0.0364(6) 0.0509(7) -0.0014(6) 0.0019(6) 0.0014(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C14 1.2243(15) . ? N13 C14 1.3353(16) . ? N13 C12 1.4786(17) . ? N13 H13 0.8598 . ? C1 C2 1.5181(18) . ? C1 C14 1.5236(17) . ? C1 C12 1.5628(17) . ? C1 H1 0.9802 . ? C2 C3 1.5221(17) . ? C2 H2A 0.9698 . ? C2 H2B 0.9708 . ? C3 C4 1.5157(19) . ? C3 H3A 0.9694 . ? C3 H3B 0.9710 . ? C4 C5 1.526(2) . ? C4 H4A 0.9696 . ? C4 H4B 0.9705 . ? C5 C6 1.525(2) . ? C5 H5A 0.9708 . ? C5 H5B 0.9696 . ? C6 C7 1.525(2) . ? C6 H6A 0.9704 . ? C6 H6B 0.9709 . ? C7 C8 1.524(2) . ? C7 H7A 0.9701 . ? C7 H7B 0.9689 . ? C8 C9 1.530(2) . ? C8 H8A 0.9706 . ? C8 H8B 0.9699 . ? C9 C10 1.514(2) . ? C9 H9A 0.9705 . ? C9 H9B 0.9690 . ? C10 C11 1.526(2) . ? C10 H10A 0.9705 . ? C10 H10B 0.9700 . ? C11 C12 1.518(2) . ? C11 H11A 0.9701 . ? C11 H11B 0.9700 . ? C12 H12 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 C14 N13 C12 95.35(10) . . ? C14 N13 H13 132.5 . . ? C12 N13 H13 132.2 . . ? C2 C1 C14 112.57(10) . . ? C2 C1 C12 117.14(11) . . ? C14 C1 C12 84.86(9) . . ? C2 C1 H1 113.1 . . ? C14 C1 H1 113.1 . . ? C12 C1 H1 113.1 . . ? C1 C2 C3 114.63(10) . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? C3 C2 H2B 108.6 . . ? H2A C2 H2B 107.5 . . ? C4 C3 C2 115.65(11) . . ? C4 C3 H3A 108.4 . . ? C2 C3 H3A 108.4 . . ? C4 C3 H3B 108.3 . . ? C2 C3 H3B 108.4 . . ? H3A C3 H3B 107.5 . . ? C3 C4 C5 113.25(13) . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4B 108.9 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.7 . . ? C4 C5 C6 114.35(13) . . ? C4 C5 H5A 108.6 . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5B 108.7 . . ? C6 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C7 C6 C5 114.78(15) . . ? C7 C6 H6A 108.5 . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6B 108.6 . . ? C5 C6 H6B 108.5 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C6 115.02(15) . . ? C8 C7 H7A 108.4 . . ? C6 C7 H7A 108.5 . . ? C8 C7 H7B 108.7 . . ? C6 C7 H7B 108.5 . . ? H7A C7 H7B 107.6 . . ? C7 C8 C9 114.97(12) . . ? C7 C8 H8A 108.4 . . ? C9 C8 H8A 108.5 . . ? C7 C8 H8B 108.6 . . ? C9 C8 H8B 108.6 . . ? H8A C8 H8B 107.5 . . ? C10 C9 C8 113.72(14) . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9B 108.7 . . ? C8 C9 H9B 108.9 . . ? H9A C9 H9B 107.6 . . ? C9 C10 C11 116.91(14) . . ? C9 C10 H10A 108.0 . . ? C11 C10 H10A 108.0 . . ? C9 C10 H10B 108.1 . . ? C11 C10 H10B 108.1 . . ? H10A C10 H10B 107.3 . . ? C12 C11 C10 115.57(12) . . ? C12 C11 H11A 108.4 . . ? C10 C11 H11A 108.4 . . ? C12 C11 H11B 108.4 . . ? C10 C11 H11B 108.4 . . ? H11A C11 H11B 107.4 . . ? N13 C12 C11 113.23(12) . . ? N13 C12 C1 86.43(9) . . ? C11 C12 C1 118.29(12) . . ? N13 C12 H12 112.2 . . ? C11 C12 H12 112.1 . . ? C1 C12 H12 112.2 . . ? O1 C14 N13 130.92(12) . . ? O1 C14 C1 135.62(12) . . ? N13 C14 C1 93.33(10) . . ? 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 C14 C1 C2 C3 166.73(11) . . . . ? C12 C1 C2 C3 70.76(14) . . . . ? C1 C2 C3 C4 68.73(15) . . . . ? C2 C3 C4 C5 -179.25(12) . . . . ? C3 C4 C5 C6 62.23(19) . . . . ? C4 C5 C6 C7 67.82(19) . . . . ? C5 C6 C7 C8 -143.18(14) . . . . ? C6 C7 C8 C9 69.9(2) . . . . ? C7 C8 C9 C10 65.21(19) . . . . ? C8 C9 C10 C11 -177.56(13) . . . . ? C9 C10 C11 C12 68.27(19) . . . . ? C14 N13 C12 C11 -117.91(13) . . . . ? C14 N13 C12 C1 1.42(10) . . . . ? C10 C11 C12 N13 162.41(13) . . . . ? C10 C11 C12 C1 63.55(18) . . . . ? C2 C1 C12 N13 111.51(12) . . . . ? C14 C1 C12 N13 -1.25(9) . . . . ? C2 C1 C12 C11 -133.96(13) . . . . ? C14 C1 C12 C11 113.28(13) . . . . ? C12 N13 C14 O1 -177.84(15) . . . . ? C12 N13 C14 C1 -1.46(11) . . . . ? C2 C1 C14 O1 60.2(2) . . . . ? C12 C1 C14 O1 177.47(17) . . . . ? C2 C1 C14 N13 -115.92(12) . . . . ? C12 C1 C14 N13 1.38(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N13 H13 O1 0.86 2.02 2.8351(15) 158.3 2_755 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 75.59 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.139 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.031 #===END data_formII _database_code_depnum_ccdc_archive 'CCDC 241105' _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-13-azabicyclo[12.2.0]tetradecan-14-one ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H23 N O' _chemical_formula_sum 'C13 H23 N O' _chemical_formula_weight 209.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 5.962(1) _cell_length_b 7.267(1) _cell_length_c 28.689(1) _cell_angle_alpha 90.00 _cell_angle_beta 94.90(1) _cell_angle_gamma 90.00 _cell_volume 1238.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15.03 _cell_measurement_theta_max 19.33 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.123 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.536 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.7866 _exptl_absorpt_correction_T_max 0.9674 _exptl_absorpt_process_details ? _exptl_special_details ; The diffraction pattern showed non-merohedral twinning, and from the two data sets the twin law could be derived. Twinning was accounted for by using the program TWINLAW with a reciprocal distance threshold of 0.005 A-1 between overlapping peaks. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'CU k\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 3 _diffrn_reflns_number 10892 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 75.14 _reflns_number_total 10892 _reflns_number_gt 6416 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express' _computing_cell_refinement 'CAD4 Express' _computing_data_reduction 'XCAD4 (Harms 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. Because of twinning, equivalent reflections were not merged during the refinement. ; _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^)+(0.1088P)^2^+2.0267P] 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 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10892 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1221 _refine_ls_R_factor_gt 0.0830 _refine_ls_wR_factor_ref 0.2907 _refine_ls_wR_factor_gt 0.2765 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 O1 O 0.8733(4) 0.7074(2) 0.20653(6) 0.0638(6) Uani 1 1 d . . . N13 N 0.8832(4) 0.3878(3) 0.21443(7) 0.0556(6) Uani 1 1 d . . . H13 H 0.9830 0.3565 0.2364 0.072 Uiso 1 1 d R . . C1 C 0.6566(4) 0.4636(3) 0.15839(7) 0.0416(5) Uani 1 1 d . . . H1 H 0.4994 0.4974 0.1615 0.050 Uiso 1 1 d R . . C2 C 0.7249(5) 0.4936(3) 0.10903(7) 0.0492(6) Uani 1 1 d . . . H2A H 0.6867 0.6189 0.0998 0.059 Uiso 1 1 d R . . H2B H 0.8872 0.4819 0.1098 0.059 Uiso 1 1 d R . . C3 C 0.6191(5) 0.3641(3) 0.07140(8) 0.0510(6) Uani 1 1 d . . . H3A H 0.6461 0.2384 0.0818 0.061 Uiso 1 1 d R . . H3B H 0.6956 0.3812 0.0432 0.061 Uiso 1 1 d R . . C4 C 0.3686(5) 0.3884(3) 0.05915(8) 0.0523(7) Uani 1 1 d . . . H4A H 0.2918 0.3781 0.0875 0.063 Uiso 1 1 d R . . H4B H 0.3415 0.5112 0.0467 0.063 Uiso 1 1 d R . . C5 C 0.2675(5) 0.2476(3) 0.02338(8) 0.0558(7) Uani 1 1 d . . . H5A H 0.3510 0.2525 -0.0042 0.067 Uiso 1 1 d R . . H5B H 0.1133 0.2827 0.0139 0.067 Uiso 1 1 d R . . C6 C 0.2690(5) 0.0493(3) 0.04141(8) 0.0560(7) Uani 1 1 d . . . H6A H 0.4209 0.0184 0.0537 0.067 Uiso 1 1 d R . . H6B H 0.2287 -0.0323 0.0153 0.067 Uiso 1 1 d R . . C7 C 0.1102(5) 0.0137(4) 0.07927(9) 0.0583(7) Uani 1 1 d . . . H7A H -0.0312 -0.0323 0.0645 0.070 Uiso 1 1 d R . . H7B H 0.0794 0.1299 0.0941 0.070 Uiso 1 1 d R . . C8 C 0.1975(6) -0.1216(3) 0.11678(9) 0.0660(8) Uani 1 1 d . . . H8A H 0.0765 -0.1500 0.1362 0.079 Uiso 1 1 d R . . H8B H 0.2383 -0.2348 0.1017 0.079 Uiso 1 1 d R . . C9 C 0.3999(6) -0.0546(3) 0.14832(9) 0.0601(8) Uani 1 1 d . . . H9A H 0.5189 -0.0203 0.1290 0.072 Uiso 1 1 d R . . H9B H 0.4554 -0.1552 0.1684 0.072 Uiso 1 1 d R . . C10 C 0.3479(5) 0.1087(3) 0.17878(8) 0.0525(7) Uani 1 1 d . . . H10A H 0.2316 0.0723 0.1986 0.063 Uiso 1 1 d R . . H10B H 0.2868 0.2068 0.1586 0.063 Uiso 1 1 d R . . C11 C 0.5442(5) 0.1840(3) 0.20947(8) 0.0548(7) Uani 1 1 d . . . H11A H 0.4877 0.2707 0.2314 0.066 Uiso 1 1 d R . . H11B H 0.6148 0.0835 0.2275 0.066 Uiso 1 1 d R . . C12 C 0.7226(4) 0.2798(3) 0.18328(7) 0.0453(6) Uani 1 1 d . . . H12 H 0.7985 0.1953 0.1631 0.054 Uiso 1 1 d R . . C14 C 0.8188(4) 0.5510(3) 0.19649(7) 0.0450(6) 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 O1 0.0837(15) 0.0568(10) 0.0480(10) -0.0061(8) -0.0114(10) -0.0161(11) N13 0.0613(15) 0.0566(12) 0.0453(11) -0.0027(9) -0.0160(11) 0.0037(12) C1 0.0483(14) 0.0416(12) 0.0337(10) -0.0001(8) -0.0027(11) 0.0022(12) C2 0.0562(16) 0.0545(13) 0.0366(11) 0.0009(10) 0.0015(12) -0.0067(13) C3 0.0580(17) 0.0558(14) 0.0394(12) -0.0065(10) 0.0055(12) -0.0050(14) C4 0.0625(18) 0.0506(14) 0.0424(12) -0.0036(10) -0.0043(13) 0.0022(13) C5 0.0655(18) 0.0661(15) 0.0338(11) -0.0057(11) -0.0072(13) -0.0022(15) C6 0.0658(18) 0.0584(15) 0.0429(12) -0.0174(11) -0.0007(13) -0.0031(15) C7 0.0562(17) 0.0638(16) 0.0539(14) -0.0109(12) -0.0006(14) -0.0071(15) C8 0.089(2) 0.0480(14) 0.0604(16) -0.0045(12) 0.0053(17) -0.0106(16) C9 0.081(2) 0.0411(13) 0.0563(14) 0.0010(10) -0.0041(16) 0.0054(15) C10 0.0650(18) 0.0453(13) 0.0477(13) 0.0031(10) 0.0081(14) -0.0005(13) C11 0.079(2) 0.0482(13) 0.0376(12) 0.0020(10) 0.0051(14) 0.0001(15) C12 0.0552(15) 0.0460(12) 0.0332(11) -0.0013(9) -0.0047(12) 0.0081(12) C14 0.0508(15) 0.0524(13) 0.0306(10) -0.0030(9) -0.0032(11) -0.0042(13) _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 O1 C14 1.210(3) . ? N13 C14 1.336(3) . ? N13 C12 1.478(3) . ? N13 H13 0.8599 . ? C1 C2 1.522(3) . ? C1 C14 1.534(3) . ? C1 C12 1.549(3) . ? C1 H1 0.9800 . ? C2 C3 1.527(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.515(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9699 . ? C4 C5 1.535(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9701 . ? C5 C6 1.531(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.523(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9699 . ? C7 C8 1.517(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.525(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9701 . ? C9 C10 1.521(3) . ? C9 H9A 0.9698 . ? C9 H9B 0.9702 . ? C10 C11 1.506(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9701 . ? C11 C12 1.522(4) . ? C11 H11A 0.9701 . ? C11 H11B 0.9700 . ? C12 H12 0.9801 . ? 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 C14 N13 C12 95.07(18) . . ? C14 N13 H13 132.5 . . ? C12 N13 H13 132.5 . . ? C2 C1 C14 113.6(2) . . ? C2 C1 C12 118.3(2) . . ? C14 C1 C12 84.75(16) . . ? C2 C1 H1 112.5 . . ? C14 C1 H1 112.4 . . ? C12 C1 H1 112.4 . . ? C1 C2 C3 116.2(2) . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2A 108.2 . . ? C1 C2 H2B 108.2 . . ? C3 C2 H2B 108.2 . . ? H2A C2 H2B 107.4 . . ? C4 C3 C2 115.6(2) . . ? C4 C3 H3A 108.4 . . ? C2 C3 H3A 108.4 . . ? C4 C3 H3B 108.4 . . ? C2 C3 H3B 108.4 . . ? H3A C3 H3B 107.5 . . ? C3 C4 C5 113.6(2) . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4B 108.8 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 114.2(2) . . ? C6 C5 H5A 108.7 . . ? C4 C5 H5A 108.7 . . ? C6 C5 H5B 108.7 . . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C7 C6 C5 114.5(2) . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6B 108.7 . . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C6 114.8(3) . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7A 108.5 . . ? C8 C7 H7B 108.6 . . ? C6 C7 H7B 108.6 . . ? H7A C7 H7B 107.5 . . ? C7 C8 C9 114.9(2) . . ? C7 C8 H8A 108.5 . . ? C9 C8 H8A 108.5 . . ? C7 C8 H8B 108.6 . . ? C9 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? C10 C9 C8 113.6(3) . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9B 108.9 . . ? C8 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C9 115.6(2) . . ? C11 C10 H10A 108.4 . . ? C9 C10 H10A 108.3 . . ? C11 C10 H10B 108.4 . . ? C9 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? C10 C11 C12 114.75(19) . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11A 108.6 . . ? C10 C11 H11B 108.6 . . ? C12 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? N13 C12 C11 112.84(18) . . ? N13 C12 C1 86.98(16) . . ? C11 C12 C1 117.5(2) . . ? N13 C12 H12 112.4 . . ? C11 C12 H12 112.4 . . ? C1 C12 H12 112.4 . . ? O1 C14 N13 132.8(2) . . ? O1 C14 C1 134.3(2) . . ? N13 C14 C1 92.85(18) . . ? 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 C14 C1 C2 C3 161.4(2) . . . . ? C12 C1 C2 C3 64.3(3) . . . . ? C1 C2 C3 C4 68.6(3) . . . . ? C2 C3 C4 C5 -176.5(2) . . . . ? C3 C4 C5 C6 66.7(3) . . . . ? C4 C5 C6 C7 68.7(3) . . . . ? C5 C6 C7 C8 -144.0(2) . . . . ? C6 C7 C8 C9 67.4(3) . . . . ? C7 C8 C9 C10 65.8(3) . . . . ? C8 C9 C10 C11 -178.1(2) . . . . ? C9 C10 C11 C12 69.0(3) . . . . ? C14 N13 C12 C11 -113.9(2) . . . . ? C14 N13 C12 C1 4.7(2) . . . . ? C10 C11 C12 N13 166.8(2) . . . . ? C10 C11 C12 C1 67.9(3) . . . . ? C2 C1 C12 N13 110.0(2) . . . . ? C14 C1 C12 N13 -4.07(18) . . . . ? C2 C1 C12 C11 -135.8(2) . . . . ? C14 C1 C12 C11 110.2(2) . . . . ? C12 N13 C14 O1 176.4(3) . . . . ? C12 N13 C14 C1 -4.7(2) . . . . ? C2 C1 C14 O1 64.6(4) . . . . ? C12 C1 C14 O1 -176.7(3) . . . . ? C2 C1 C14 N13 -114.2(2) . . . . ? C12 C1 C14 N13 4.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N13 H13 O1 0.86 2.09 2.899(3) 157.7 4_756 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 75.40 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.341 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.080 #===END