# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_strohmann6d _database_code_depnum_ccdc_archive 'CCDC 856271' #TrackingRef 'strohmann-cpd-6d.cif' _audit_creation_date ? _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H25 N O' _chemical_formula_sum 'C23 H25 N O' _chemical_formula_weight 331.44 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' _symmetry_cell_setting ? _symmetry_space_group_name_Hall 'F 2 -2d' _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 39.761(4) _cell_length_b 30.556(3) _cell_length_c 5.9332(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7208.5(11) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2848 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9571 _exptl_absorpt_correction_T_max 0.9854 _exptl_absorpt_process_details 'CrysAlis Red (Oxford Diffraction 2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 9834 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.1601 _diffrn_reflns_limit_h_min -48 _diffrn_reflns_limit_h_max 48 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3448 _reflns_number_gt 1818 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2006)' _computing_cell_refinement 'CrysAlis Red (Oxford Diffraction, 2006)' _computing_data_reduction 'CrysAlis Red (Oxford Diffraction, 2006)' _computing_structure_solution 'SHELXS-90 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 V1.073 (Farrugia, 2001)' _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3448 _refine_ls_number_parameters 229 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0367 _refine_ls_wR_factor_gt 0.0344 _refine_ls_goodness_of_fit_ref 0.843 _refine_ls_restrained_S_all 0.843 _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 C1 C 0.32739(6) 0.07779(9) 0.5497(4) 0.0202(7) Uani 1 1 d . . . C2 C 0.31216(6) 0.03278(8) 0.5107(4) 0.0171(7) Uani 1 1 d . . . C3 C 0.29388(5) 0.01352(8) 0.6858(4) 0.0222(7) Uani 1 1 d . . . H3 H 0.2927 0.0276 0.8283 0.027 Uiso 1 1 calc R . . C4 C 0.27753(6) -0.02583(8) 0.6535(4) 0.0234(7) Uani 1 1 d . . . H4 H 0.2650 -0.0385 0.7733 0.028 Uiso 1 1 calc R . . C5 C 0.27931(6) -0.04696(8) 0.4471(4) 0.0245(7) Uani 1 1 d . . . H5 H 0.2683 -0.0742 0.4257 0.029 Uiso 1 1 calc R . . C6 C 0.29724(6) -0.02814(8) 0.2723(4) 0.0241(7) Uani 1 1 d . . . H6 H 0.2984 -0.0425 0.1305 0.029 Uiso 1 1 calc R . . C7 C 0.31361(6) 0.01167(8) 0.3032(4) 0.0197(7) Uani 1 1 d . . . H7 H 0.3258 0.0245 0.1822 0.024 Uiso 1 1 calc R . . C8 C 0.29998(6) 0.11285(8) 0.5102(4) 0.0171(7) Uani 1 1 d . . . C9 C 0.28332(6) 0.11478(8) 0.3028(4) 0.0210(7) Uani 1 1 d . . . H9 H 0.2890 0.0948 0.1862 0.025 Uiso 1 1 calc R . . C10 C 0.25848(5) 0.14588(8) 0.2677(4) 0.0248(7) Uani 1 1 d . . . H10 H 0.2474 0.1474 0.1260 0.030 Uiso 1 1 calc R . . C11 C 0.24962(6) 0.17487(9) 0.4379(4) 0.0267(7) Uani 1 1 d . . . H11 H 0.2326 0.1962 0.4137 0.032 Uiso 1 1 calc R . . C12 C 0.26576(6) 0.17223(8) 0.6407(4) 0.0283(8) Uani 1 1 d . . . H12 H 0.2599 0.1920 0.7578 0.034 Uiso 1 1 calc R . . C13 C 0.29065(6) 0.14108(8) 0.6785(5) 0.0255(7) Uani 1 1 d . . . H13 H 0.3012 0.1394 0.8218 0.031 Uiso 1 1 calc R . . C14 C 0.35766(6) 0.08800(8) 0.3886(4) 0.0156(7) Uani 1 1 d . . . H14 H 0.3478 0.0892 0.2336 0.019 Uiso 1 1 calc R . . C15 C 0.38536(6) 0.05347(9) 0.3776(4) 0.0217(7) Uani 1 1 d . . . C16 C 0.40493(6) 0.05239(8) 0.1842(4) 0.0228(7) Uani 1 1 d . . . H16 H 0.3994 0.0713 0.0627 0.027 Uiso 1 1 calc R . . C17 C 0.43230(6) 0.02458(8) 0.1626(4) 0.0303(8) Uani 1 1 d . . . H17 H 0.4454 0.0246 0.0286 0.036 Uiso 1 1 calc R . . C18 C 0.44031(6) -0.00329(8) 0.3388(4) 0.0267(8) Uani 1 1 d . . . H18 H 0.4592 -0.0222 0.3275 0.032 Uiso 1 1 calc R . . C19 C 0.42067(6) -0.00336(8) 0.5313(4) 0.0253(7) Uani 1 1 d . . . H19 H 0.4260 -0.0227 0.6515 0.030 Uiso 1 1 calc R . . C20 C 0.39328(6) 0.02444(7) 0.5508(4) 0.0204(7) Uani 1 1 d . . . H20 H 0.3798 0.0237 0.6831 0.024 Uiso 1 1 calc R . . C21 C 0.37198(5) 0.13423(7) 0.4335(4) 0.0208(7) Uani 1 1 d . . . H21A H 0.3906 0.1399 0.3266 0.025 Uiso 1 1 calc R . . H21B H 0.3542 0.1561 0.4045 0.025 Uiso 1 1 calc R . . C22 C 0.37884(5) 0.18503(8) 0.7457(4) 0.0346(8) Uani 1 1 d . . . H22A H 0.3863 0.1879 0.9025 0.052 Uiso 1 1 calc R . . H22B H 0.3548 0.1919 0.7357 0.052 Uiso 1 1 calc R . . H22C H 0.3916 0.2054 0.6508 0.052 Uiso 1 1 calc R . . C23 C 0.42077(5) 0.12926(7) 0.6849(4) 0.0302(8) Uani 1 1 d . . . H23A H 0.4336 0.1487 0.5857 0.045 Uiso 1 1 calc R . . H23B H 0.4244 0.0988 0.6395 0.045 Uiso 1 1 calc R . . H23C H 0.4283 0.1332 0.8409 0.045 Uiso 1 1 calc R . . N N 0.38466(5) 0.13995(7) 0.6679(3) 0.0218(6) Uani 1 1 d . . . O O 0.33878(4) 0.07957(5) 0.7794(2) 0.0189(4) Uani 1 1 d . . . H0 H 0.3545 0.0978 0.7905 0.028 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 C1 0.0230(17) 0.0280(19) 0.0096(15) -0.0028(16) 0.0039(14) -0.0036(15) C2 0.0130(15) 0.0154(16) 0.0228(17) -0.0014(15) -0.0011(14) 0.0016(13) C3 0.0187(16) 0.0229(17) 0.0249(17) 0.0022(16) -0.0015(14) 0.0010(15) C4 0.0194(16) 0.0227(19) 0.0282(19) 0.0135(18) 0.0023(15) -0.0004(15) C5 0.0219(17) 0.0139(17) 0.038(2) 0.0051(17) -0.0084(15) -0.0019(15) C6 0.0213(16) 0.0226(19) 0.0283(18) -0.0067(16) -0.0040(14) 0.0064(15) C7 0.0216(17) 0.0166(16) 0.0209(17) 0.0020(16) 0.0006(14) -0.0004(14) C8 0.0165(15) 0.0159(17) 0.0191(17) 0.0034(15) 0.0021(14) 0.0001(14) C9 0.0227(17) 0.0219(18) 0.0183(16) -0.0080(16) -0.0025(14) 0.0024(14) C10 0.0219(17) 0.0265(19) 0.0261(18) 0.0055(16) -0.0039(15) -0.0014(15) C11 0.0198(16) 0.026(2) 0.0344(18) 0.0014(18) -0.0001(15) 0.0082(15) C12 0.0327(19) 0.028(2) 0.0248(18) -0.0123(18) 0.0061(15) 0.0018(16) C13 0.0230(17) 0.0292(19) 0.0245(17) 0.0037(18) -0.0030(14) 0.0049(16) C14 0.0191(16) 0.0205(17) 0.0071(15) 0.0047(14) -0.0020(12) 0.0003(14) C15 0.0147(16) 0.0217(18) 0.0286(18) -0.0048(15) -0.0028(14) -0.0061(14) C16 0.0291(18) 0.0222(17) 0.0172(16) 0.0024(15) 0.0034(14) 0.0040(15) C17 0.0259(18) 0.037(2) 0.0276(18) -0.0054(18) 0.0060(16) -0.0027(16) C18 0.0183(17) 0.024(2) 0.038(2) -0.0060(17) -0.0009(15) 0.0027(15) C19 0.0285(18) 0.0174(18) 0.0300(17) -0.0026(17) -0.0057(16) -0.0025(15) C20 0.0229(16) 0.0198(17) 0.0186(15) -0.0017(17) 0.0042(14) -0.0059(15) C21 0.0181(16) 0.0190(18) 0.0253(16) 0.0075(16) -0.0012(14) 0.0008(14) C22 0.0307(19) 0.032(2) 0.041(2) -0.0106(17) -0.0063(15) 0.0032(16) C23 0.0283(17) 0.0187(17) 0.0436(19) 0.0031(16) -0.0081(16) 0.0003(15) N 0.0193(13) 0.0186(14) 0.0274(14) -0.0008(13) -0.0036(12) -0.0023(12) O 0.0203(11) 0.0225(12) 0.0140(10) 0.0001(10) -0.0061(8) -0.0049(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 C1 O 1.438(2) . ? C1 C2 1.521(3) . ? C1 C8 1.546(3) . ? C1 C14 1.568(3) . ? C2 C7 1.391(3) . ? C2 C3 1.398(3) . ? C3 C4 1.380(3) . ? C4 C5 1.387(3) . ? C5 C6 1.383(3) . ? C6 C7 1.392(3) . ? C8 C13 1.371(3) . ? C8 C9 1.398(3) . ? C9 C10 1.386(3) . ? C10 C11 1.389(3) . ? C11 C12 1.366(3) . ? C12 C13 1.391(3) . ? C14 C15 1.527(3) . ? C14 C21 1.546(3) . ? C15 C20 1.393(3) . ? C15 C16 1.387(3) . ? C16 C17 1.386(3) . ? C17 C18 1.386(3) . ? C18 C19 1.384(3) . ? C19 C20 1.386(3) . ? C21 N 1.490(3) . ? C22 N 1.471(3) . ? C23 N 1.476(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 O C1 C2 107.7(2) . . ? O C1 C8 109.9(2) . . ? C2 C1 C8 108.84(19) . . ? O C1 C14 109.18(18) . . ? C2 C1 C14 113.1(2) . . ? C8 C1 C14 108.1(2) . . ? C7 C2 C3 119.0(2) . . ? C7 C2 C1 122.5(2) . . ? C3 C2 C1 118.3(2) . . ? C4 C3 C2 120.6(3) . . ? C5 C4 C3 120.3(3) . . ? C6 C5 C4 119.6(2) . . ? C5 C6 C7 120.4(2) . . ? C2 C7 C6 120.1(2) . . ? C13 C8 C9 119.1(3) . . ? C13 C8 C1 121.1(2) . . ? C9 C8 C1 119.8(2) . . ? C10 C9 C8 119.9(3) . . ? C9 C10 C11 120.6(3) . . ? C12 C11 C10 118.9(3) . . ? C11 C12 C13 121.1(3) . . ? C8 C13 C12 120.4(3) . . ? C15 C14 C21 111.92(19) . . ? C15 C14 C1 116.3(2) . . ? C21 C14 C1 111.1(2) . . ? C20 C15 C16 117.9(3) . . ? C20 C15 C14 124.9(2) . . ? C16 C15 C14 117.2(2) . . ? C17 C16 C15 122.1(3) . . ? C18 C17 C16 119.2(3) . . ? C19 C18 C17 119.6(3) . . ? C18 C19 C20 120.8(3) . . ? C19 C20 C15 120.4(2) . . ? N C21 C14 113.12(19) . . ? C22 N C23 109.80(18) . . ? C22 N C21 110.46(19) . . ? C23 N C21 111.54(19) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.187 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.035 data_strohmann6e _database_code_depnum_ccdc_archive 'CCDC 856272' #TrackingRef 'strohmann-cpd-6e.cif' _audit_creation_date ? _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H25 N O' _chemical_formula_sum 'C16 H25 N O' _chemical_formula_weight 247.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 8.3576(10) _cell_length_b 19.611(2) _cell_length_c 8.8256(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1446.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.136 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9727 _exptl_absorpt_correction_T_max 0.9862 _exptl_absorpt_process_details 'CrysAlis Red (Oxford Diffraction 2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 5187 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0723 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2204 _reflns_number_gt 1463 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2006)' _computing_cell_refinement 'CrysAlis Red (Oxford Diffraction, 2006)' _computing_data_reduction 'CrysAlis Red (Oxford Diffraction, 2006)' _computing_structure_solution 'SHELXS-90 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 V1.073 (Farrugia, 2001)' _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^)+(0.0120P)^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_number_reflns 2204 _refine_ls_number_parameters 169 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0555 _refine_ls_wR_factor_gt 0.0531 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 0.43247(19) 0.06518(8) 0.75826(19) 0.0224(4) Uani 1 1 d . . . N1 N 0.2434(2) -0.03504(8) 0.6426(2) 0.0203(5) Uani 1 1 d . . . C4 C 0.2762(3) 0.08139(9) 0.5300(2) 0.0184(6) Uani 1 1 d . . . H4 H 0.1895 0.0957 0.6013 0.022 Uiso 1 1 calc R . . C11 C 0.4363(3) 0.09726(10) 0.6111(2) 0.0181(5) Uani 1 1 d . . . C14 C 0.7500(3) 0.16717(9) 0.6406(3) 0.0286(6) Uani 1 1 d . . . H14A H 0.8467 0.1767 0.7018 0.034 Uiso 1 1 calc R . . H14B H 0.7604 0.1918 0.5432 0.034 Uiso 1 1 calc R . . C3 C 0.2518(3) 0.00458(10) 0.5021(2) 0.0214(6) Uani 1 1 d . . . H3A H 0.1516 -0.0022 0.4442 0.026 Uiso 1 1 calc R . . H3B H 0.3413 -0.0128 0.4396 0.026 Uiso 1 1 calc R . . C13 C 0.7383(3) 0.09120(9) 0.6105(3) 0.0250(6) Uani 1 1 d . . . H13A H 0.7413 0.0663 0.7081 0.030 Uiso 1 1 calc R . . H13B H 0.8317 0.0765 0.5498 0.030 Uiso 1 1 calc R . . C10 C 0.3169(3) 0.10198(10) 0.2453(3) 0.0232(6) Uani 1 1 d . . . H10 H 0.3879 0.0642 0.2416 0.028 Uiso 1 1 calc R . . C9 C 0.2841(3) 0.13763(11) 0.1150(3) 0.0298(6) Uani 1 1 d . . . H9 H 0.3317 0.1240 0.0221 0.036 Uiso 1 1 calc R . . C16 C 0.4501(2) 0.17363(9) 0.6408(3) 0.0226(6) Uani 1 1 d . . . H16A H 0.4467 0.1983 0.5429 0.027 Uiso 1 1 calc R . . H16B H 0.3571 0.1887 0.7018 0.027 Uiso 1 1 calc R . . C12 C 0.5850(3) 0.07277(10) 0.5261(2) 0.0217(6) Uani 1 1 d . . . H12A H 0.5795 0.0227 0.5132 0.026 Uiso 1 1 calc R . . H12B H 0.5872 0.0937 0.4241 0.026 Uiso 1 1 calc R . . C5 C 0.2472(3) 0.12043(11) 0.3831(3) 0.0205(5) Uani 1 1 d . . . C6 C 0.1449(3) 0.17612(11) 0.3845(3) 0.0241(6) Uani 1 1 d . . . H6 H 0.0964 0.1898 0.4771 0.029 Uiso 1 1 calc R . . C1 C 0.2608(3) -0.10777(9) 0.6055(3) 0.0316(7) Uani 1 1 d . . . H1A H 0.1756 -0.1214 0.5355 0.047 Uiso 1 1 calc R . . H1B H 0.2534 -0.1349 0.6985 0.047 Uiso 1 1 calc R . . H1C H 0.3651 -0.1155 0.5576 0.047 Uiso 1 1 calc R . . C7 C 0.1123(3) 0.21217(11) 0.2529(3) 0.0334(7) Uani 1 1 d . . . H7 H 0.0415 0.2500 0.2556 0.040 Uiso 1 1 calc R . . C15 C 0.6035(3) 0.19234(10) 0.7239(3) 0.0274(7) Uani 1 1 d . . . H15A H 0.6096 0.2425 0.7349 0.033 Uiso 1 1 calc R . . H15B H 0.6013 0.1722 0.8267 0.033 Uiso 1 1 calc R . . C2 C 0.0901(3) -0.02515(11) 0.7186(2) 0.0326(7) Uani 1 1 d . . . H2A H 0.0805 0.0224 0.7513 0.049 Uiso 1 1 calc R . . H2B H 0.0838 -0.0552 0.8071 0.049 Uiso 1 1 calc R . . H2C H 0.0029 -0.0360 0.6483 0.049 Uiso 1 1 calc R . . C8 C 0.1828(3) 0.19299(12) 0.1182(3) 0.0346(7) Uani 1 1 d . . . H8 H 0.1615 0.2178 0.0280 0.042 Uiso 1 1 calc R . . H100 H 0.396(3) 0.0272(10) 0.753(3) 0.042(9) Uiso 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 0.0278(11) 0.0250(9) 0.0145(8) 0.0044(9) -0.0026(10) -0.0048(8) N1 0.0245(13) 0.0178(10) 0.0187(11) 0.0055(10) 0.0000(10) -0.0002(9) C4 0.0188(15) 0.0203(13) 0.0162(13) -0.0005(11) 0.0007(12) 0.0028(10) C11 0.0214(15) 0.0172(11) 0.0156(12) 0.0059(11) -0.0004(13) 0.0007(10) C14 0.0218(15) 0.0305(13) 0.0335(14) 0.0062(14) -0.0065(15) -0.0086(12) C3 0.0218(15) 0.0231(12) 0.0193(13) 0.0030(12) -0.0017(13) -0.0027(11) C13 0.0205(15) 0.0302(13) 0.0242(14) 0.0044(13) 0.0004(15) 0.0015(11) C10 0.0227(15) 0.0273(13) 0.0197(13) 0.0010(14) -0.0022(14) 0.0032(10) C9 0.0287(17) 0.0408(14) 0.0199(14) 0.0045(14) 0.0012(15) -0.0068(13) C16 0.0248(15) 0.0206(12) 0.0223(13) -0.0028(12) 0.0002(14) 0.0010(10) C12 0.0214(16) 0.0224(12) 0.0213(13) 0.0028(12) -0.0009(13) 0.0025(10) C5 0.0169(13) 0.0210(12) 0.0235(13) 0.0013(12) -0.0044(14) -0.0043(10) C6 0.0275(16) 0.0219(12) 0.0230(14) -0.0008(12) -0.0040(13) -0.0016(12) C1 0.0366(17) 0.0227(13) 0.0356(16) 0.0058(14) -0.0082(16) -0.0003(12) C7 0.0382(18) 0.0241(13) 0.0378(15) 0.0036(16) -0.0128(18) 0.0052(12) C15 0.0327(18) 0.0208(13) 0.0286(16) -0.0015(12) -0.0088(14) -0.0027(12) C2 0.0304(18) 0.0343(15) 0.0330(18) 0.0061(13) 0.0079(15) -0.0004(12) C8 0.0414(19) 0.0367(15) 0.0258(15) 0.0138(15) -0.0104(16) -0.0082(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 C11 1.443(3) . ? N1 C2 1.459(3) . ? N1 C3 1.465(2) . ? N1 C1 1.471(2) . ? C4 C5 1.525(3) . ? C4 C3 1.540(2) . ? C4 C11 1.549(3) . ? C11 C16 1.525(2) . ? C11 C12 1.529(3) . ? C14 C15 1.511(3) . ? C14 C13 1.517(2) . ? C13 C12 1.525(3) . ? C10 C9 1.373(3) . ? C10 C5 1.396(3) . ? C9 C8 1.377(3) . ? C16 C15 1.522(3) . ? C5 C6 1.387(3) . ? C6 C7 1.387(3) . ? C7 C8 1.379(4) . ? 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 C2 N1 C3 111.13(18) . . ? C2 N1 C1 108.55(16) . . ? C3 N1 C1 108.74(17) . . ? C5 C4 C3 109.50(17) . . ? C5 C4 C11 115.42(17) . . ? C3 C4 C11 112.65(17) . . ? O1 C11 C16 105.97(16) . . ? O1 C11 C12 108.81(16) . . ? C16 C11 C12 109.35(17) . . ? O1 C11 C4 108.00(17) . . ? C16 C11 C4 110.00(16) . . ? C12 C11 C4 114.36(17) . . ? C15 C14 C13 110.72(18) . . ? N1 C3 C4 112.94(17) . . ? C14 C13 C12 111.87(18) . . ? C9 C10 C5 121.0(2) . . ? C10 C9 C8 120.5(3) . . ? C15 C16 C11 112.53(17) . . ? C13 C12 C11 111.64(17) . . ? C6 C5 C10 118.0(2) . . ? C6 C5 C4 119.1(2) . . ? C10 C5 C4 123.0(2) . . ? C7 C6 C5 121.0(2) . . ? C8 C7 C6 119.9(2) . . ? C14 C15 C16 111.66(19) . . ? C9 C8 C7 119.7(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.166 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.036 data_strohmann8 _database_code_depnum_ccdc_archive 'CCDC 856273' #TrackingRef 'strohmann-cpd-8.cif' _audit_creation_date ? _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_sum 'C16 H28 Li N3' _chemical_formula_weight 269.35 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' Li Li -0.0003 0.0001 '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' 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 11.9709(7) _cell_length_b 8.4897(5) _cell_length_c 16.7872(11) _cell_angle_alpha 90.00 _cell_angle_beta 104.660(6) _cell_angle_gamma 90.00 _cell_volume 1650.54(17) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 27.0 _exptl_crystal_description blocks _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.084 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9812 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_process_details 'CrysAlis Red (Oxford Diffraction 2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 20439 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3253 _reflns_number_gt 1929 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2006)' _computing_cell_refinement 'CrysAlis Red (Oxford Diffraction, 2006)' _computing_data_reduction 'CrysAlis Red (Oxford Diffraction, 2006)' _computing_structure_solution 'SHELXS-90 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 V1.073 (Farrugia, 2001)' _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^)+(0.0296P)^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_number_reflns 3253 _refine_ls_number_parameters 198 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0831 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.0797 _refine_ls_wR_factor_gt 0.0756 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 Li Li 0.21927(19) 0.1969(3) 0.14060(14) 0.0284(6) Uani 1 1 d . . . C1 C 0.38993(13) 0.08313(19) 0.31340(9) 0.0430(4) Uani 1 1 d . . . H1A H 0.4023 -0.0155 0.3447 0.065 Uiso 1 1 calc R . . H1B H 0.3478 0.1574 0.3397 0.065 Uiso 1 1 calc R . . H1C H 0.4647 0.1286 0.3121 0.065 Uiso 1 1 calc R . . N1 N 0.32287(9) 0.05158(13) 0.22938(6) 0.0268(3) Uani 1 1 d . . . C2 C 0.38905(12) -0.05274(18) 0.18844(8) 0.0352(4) Uani 1 1 d . . . H2A H 0.4072 -0.1518 0.2202 0.042 Uiso 1 1 calc R . . H2B H 0.4629 -0.0013 0.1875 0.042 Uiso 1 1 calc R . . N2 N 0.25881(9) 0.32829(14) 0.04794(7) 0.0284(3) Uani 1 1 d . . . C3 C 0.32293(12) -0.09020(16) 0.10174(8) 0.0264(3) Uani 1 1 d . . . N3 N 0.16026(9) 0.40320(13) 0.18512(7) 0.0282(3) Uani 1 1 d . . . C4 C 0.37976(12) -0.12343(17) 0.04185(9) 0.0340(4) Uani 1 1 d . . . H4 H 0.4618 -0.1234 0.0564 0.041 Uiso 1 1 calc R . . C5 C 0.32196(14) -0.15679(18) -0.03840(9) 0.0374(4) Uani 1 1 d . . . H5 H 0.3627 -0.1800 -0.0787 0.045 Uiso 1 1 calc R . . C6 C 0.20207(13) -0.15523(17) -0.05824(9) 0.0354(4) Uani 1 1 d . . . H6 H 0.1602 -0.1774 -0.1132 0.043 Uiso 1 1 calc R . . C7 C 0.14284(12) -0.12225(16) -0.00005(9) 0.0298(4) Uani 1 1 d . . . H7 H 0.0608 -0.1237 -0.0158 0.036 Uiso 1 1 calc R . . C8 C 0.19971(12) -0.08611(15) 0.08278(9) 0.0251(3) Uani 1 1 d . . . C9 C 0.14337(14) -0.04213(17) 0.14310(9) 0.0287(4) Uani 1 1 d . . . H9 H 0.0635(12) -0.0513(15) 0.1322(8) 0.034(4) Uiso 1 1 d . . . C10 C 0.21254(13) -0.0264(2) 0.22946(10) 0.0335(4) Uani 1 1 d . . . H10A H 0.1742(10) 0.0412(14) 0.2660(7) 0.024(3) Uiso 1 1 d . . . H10B H 0.2314(12) -0.1303(19) 0.2626(8) 0.051(5) Uiso 1 1 d . . . C11 C 0.17613(13) 0.29065(19) -0.02969(9) 0.0445(4) Uani 1 1 d . . . H11A H 0.0975 0.2988 -0.0227 0.067 Uiso 1 1 calc R . . H11B H 0.1897 0.1831 -0.0462 0.067 Uiso 1 1 calc R . . H11C H 0.1856 0.3647 -0.0723 0.067 Uiso 1 1 calc R . . C12 C 0.37607(12) 0.3073(2) 0.03861(10) 0.0464(5) Uani 1 1 d . . . H12A H 0.3842 0.2010 0.0181 0.070 Uiso 1 1 calc R . . H12B H 0.4316 0.3218 0.0921 0.070 Uiso 1 1 calc R . . H12C H 0.3910 0.3851 -0.0006 0.070 Uiso 1 1 calc R . . C13 C 0.24403(14) 0.49155(18) 0.07286(10) 0.0457(5) Uani 1 1 d . . . H13A H 0.2294 0.5607 0.0238 0.055 Uiso 1 1 calc R . . H13B H 0.3161 0.5275 0.1119 0.055 Uiso 1 1 calc R . . C14 C 0.14559(13) 0.50546(19) 0.11285(9) 0.0427(4) Uani 1 1 d . . . H14A H 0.1393 0.6162 0.1297 0.051 Uiso 1 1 calc R . . H14B H 0.0728 0.4775 0.0723 0.051 Uiso 1 1 calc R . . C15 C 0.25213(14) 0.4640(2) 0.25238(10) 0.0531(5) Uani 1 1 d . . . H15A H 0.2372 0.5751 0.2618 0.080 Uiso 1 1 calc R . . H15B H 0.3263 0.4543 0.2381 0.080 Uiso 1 1 calc R . . H15C H 0.2547 0.4035 0.3025 0.080 Uiso 1 1 calc R . . C16 C 0.05349(13) 0.4003(2) 0.21157(11) 0.0602(6) Uani 1 1 d . . . H16A H 0.0370 0.5062 0.2288 0.090 Uiso 1 1 calc R . . H16B H 0.0617 0.3272 0.2579 0.090 Uiso 1 1 calc R . . H16C H -0.0101 0.3656 0.1658 0.090 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 Li 0.0327(14) 0.0245(14) 0.0289(14) 0.0022(11) 0.0096(11) 0.0000(10) C1 0.0467(10) 0.0466(11) 0.0325(10) 0.0008(8) 0.0038(8) 0.0042(8) N1 0.0283(7) 0.0299(7) 0.0215(7) -0.0010(5) 0.0050(6) 0.0023(5) C2 0.0292(9) 0.0338(10) 0.0414(10) 0.0013(8) 0.0065(8) 0.0101(7) N2 0.0347(7) 0.0237(7) 0.0295(7) -0.0009(6) 0.0131(6) -0.0011(6) C3 0.0306(9) 0.0207(8) 0.0281(9) 0.0027(7) 0.0078(7) 0.0053(7) N3 0.0298(7) 0.0260(7) 0.0312(7) -0.0017(6) 0.0122(6) -0.0006(6) C4 0.0310(9) 0.0293(10) 0.0429(10) 0.0030(8) 0.0117(8) 0.0047(7) C5 0.0491(11) 0.0334(10) 0.0361(10) 0.0001(8) 0.0225(9) 0.0029(8) C6 0.0515(11) 0.0268(9) 0.0263(9) 0.0007(7) 0.0067(8) -0.0043(7) C7 0.0313(9) 0.0226(9) 0.0337(9) 0.0014(7) 0.0051(8) -0.0043(6) C8 0.0300(9) 0.0143(7) 0.0308(9) 0.0043(7) 0.0071(7) 0.0006(6) C9 0.0266(9) 0.0293(9) 0.0306(9) -0.0006(7) 0.0082(8) -0.0012(7) C10 0.0362(10) 0.0285(10) 0.0384(11) 0.0035(8) 0.0144(8) 0.0012(8) C11 0.0565(11) 0.0427(12) 0.0333(10) 0.0058(8) 0.0094(9) 0.0014(9) C12 0.0438(11) 0.0502(12) 0.0524(11) 0.0002(9) 0.0256(9) -0.0050(8) C13 0.0773(13) 0.0232(9) 0.0467(11) 0.0026(8) 0.0343(10) -0.0007(9) C14 0.0587(11) 0.0263(10) 0.0446(10) 0.0017(8) 0.0161(9) 0.0145(8) C15 0.0598(12) 0.0484(12) 0.0473(11) -0.0140(9) 0.0066(10) 0.0016(9) C16 0.0532(12) 0.0518(13) 0.0900(15) -0.0066(11) 0.0447(11) 0.0009(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 Li N2 2.064(2) . ? Li N1 2.084(3) . ? Li N3 2.096(3) . ? Li C9 2.228(3) . ? Li C10 2.426(3) . ? Li C8 2.579(3) . ? C1 N1 1.4603(17) . ? N1 C2 1.4697(16) . ? N1 C10 1.4776(17) . ? C2 C3 1.5043(18) . ? N2 C11 1.4585(17) . ? N2 C12 1.4622(17) . ? N2 C13 1.4713(18) . ? C3 C4 1.3782(18) . ? C3 C8 1.4285(18) . ? N3 C16 1.4556(17) . ? N3 C15 1.4569(18) . ? N3 C14 1.4657(17) . ? C4 C5 1.3792(19) . ? C5 C6 1.3888(19) . ? C6 C7 1.3733(18) . ? C7 C8 1.4184(18) . ? C8 C9 1.4018(18) . ? C9 C10 1.483(2) . ? C13 C14 1.5012(18) . ? 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 Li N1 130.56(12) . . ? N2 Li N3 88.81(10) . . ? N1 Li N3 115.65(11) . . ? N2 Li C9 132.75(12) . . ? N1 Li C9 67.62(8) . . ? N3 Li C9 125.35(11) . . ? N2 Li C10 159.28(12) . . ? N1 Li C10 37.29(6) . . ? N3 Li C10 111.54(10) . . ? C9 Li C10 36.84(6) . . ? N2 Li C8 103.66(10) . . ? N1 Li C8 72.47(8) . . ? N3 Li C8 154.94(11) . . ? C9 Li C8 32.88(6) . . ? C10 Li C8 59.32(7) . . ? C1 N1 C2 109.42(11) . . ? C1 N1 C10 110.75(11) . . ? C2 N1 C10 108.56(11) . . ? C1 N1 Li 131.62(11) . . ? C2 N1 Li 108.41(9) . . ? C10 N1 Li 84.00(10) . . ? N1 C2 C3 111.46(11) . . ? C11 N2 C12 109.29(11) . . ? C11 N2 C13 110.93(12) . . ? C12 N2 C13 109.45(11) . . ? C11 N2 Li 108.76(11) . . ? C12 N2 Li 115.11(11) . . ? C13 N2 Li 103.18(10) . . ? C4 C3 C8 120.99(13) . . ? C4 C3 C2 120.87(12) . . ? C8 C3 C2 118.12(12) . . ? C16 N3 C15 108.56(12) . . ? C16 N3 C14 109.39(12) . . ? C15 N3 C14 109.90(12) . . ? C16 N3 Li 119.73(11) . . ? C15 N3 Li 108.42(11) . . ? C14 N3 Li 100.40(10) . . ? C3 C4 C5 122.43(14) . . ? C4 C5 C6 117.70(14) . . ? C7 C6 C5 121.30(14) . . ? C6 C7 C8 122.37(13) . . ? C9 C8 C7 124.50(13) . . ? C9 C8 C3 120.26(13) . . ? C7 C8 C3 115.18(12) . . ? C9 C8 Li 59.64(9) . . ? C7 C8 Li 123.07(10) . . ? C3 C8 Li 87.05(9) . . ? C8 C9 C10 118.60(14) . . ? C8 C9 Li 87.48(11) . . ? C10 C9 Li 78.86(11) . . ? N1 C10 C9 108.52(12) . . ? N1 C10 Li 58.71(9) . . ? C9 C10 Li 64.30(10) . . ? N2 C13 C14 111.45(12) . . ? N3 C14 C13 112.36(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.148 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.033 data_strohmann9 _database_code_depnum_ccdc_archive 'CCDC 856274' #TrackingRef 'strohmann-cpd-9.cif' _audit_creation_date ? _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C18 H28 K N O2' _chemical_formula_weight 329.52 _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 9.5449(6) _cell_length_b 9.8534(5) _cell_length_c 11.6027(6) _cell_angle_alpha 81.047(5) _cell_angle_beta 74.192(5) _cell_angle_gamma 61.176(6) _cell_volume 919.49(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description blocks _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.190 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.295 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.868 _exptl_absorpt_correction_T_max 0.915 _exptl_absorpt_process_details 'CrysAlis Red (Oxford Diffraction 2006)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(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 'Oxford Diffraction XCalibur S' _diffrn_reflns_number 14339 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.1100 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7893 _reflns_number_gt 4462 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2006)' _computing_cell_refinement 'CrysAlis Red (Oxford Diffraction, 2006)' _computing_data_reduction 'CrysAlis Red (Oxford Diffraction, 2006)' _computing_structure_solution 'SHELXS-90 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 V1.073 (Farrugia, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0150P)^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 -0.03(3) _refine_ls_number_reflns 7893 _refine_ls_number_parameters 431 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.0645 _refine_ls_wR_factor_gt 0.0613 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.336 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.040 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 C1 C -0.3486(4) 0.5404(4) 0.5558(3) 0.0602(10) Uani 1 1 d . . . H1A H -0.4474 0.6365 0.5731 0.090 Uiso 1 1 calc R . . H1B H -0.3614 0.4597 0.6085 0.090 Uiso 1 1 calc R . . H1C H -0.3272 0.5147 0.4742 0.090 Uiso 1 1 calc R . . K1 K -0.03370(7) 0.68761(6) 0.39604(5) 0.0413(2) Uani 1 1 d . . . N1 N -0.2116(3) 0.5558(3) 0.5735(2) 0.0388(6) Uani 1 1 d . . . O1 O -0.3141(3) 0.9555(2) 0.41085(19) 0.0590(7) Uani 1 1 d . . . C2 C -0.2423(4) 0.6050(4) 0.6950(3) 0.0459(9) Uani 1 1 d . . . H2A H -0.366(3) 0.706(3) 0.710(2) 0.055 Uiso 1 1 d . . . H2B H -0.252(3) 0.518(3) 0.766(2) 0.055 Uiso 1 1 d . . . K2 K 0.07523(7) 0.43518(6) -0.08260(5) 0.0368(2) Uani 1 1 d . . . N2 N -0.2315(3) 0.5388(3) 0.0823(2) 0.0393(6) Uani 1 1 d . . . O2 O 0.0941(3) 0.8801(3) 0.3905(2) 0.0750(8) Uani 1 1 d . . . C3 C -0.1037(3) 0.6332(3) 0.7056(2) 0.0288(8) Uani 1 1 d . . . O3 O 0.3986(2) 0.2457(2) -0.09320(19) 0.0527(6) Uani 1 1 d . . . C4 C -0.1278(4) 0.7454(4) 0.7759(3) 0.0450(10) Uani 1 1 d . . . H4 H -0.2345 0.8105 0.8152 0.054 Uiso 1 1 calc R . . O4 O 0.0443(2) 0.1815(2) -0.09924(19) 0.0472(6) Uani 1 1 d . . . C5 C -0.0039(5) 0.7661(4) 0.7909(3) 0.0506(9) Uani 1 1 d . . . H5 H -0.0244 0.8421 0.8407 0.061 Uiso 1 1 calc R . . C6 C 0.1544(4) 0.6711(4) 0.7302(3) 0.0466(10) Uani 1 1 d . . . H6 H 0.2400 0.6859 0.7390 0.056 Uiso 1 1 calc R . . C7 C 0.1899(4) 0.5561(3) 0.6575(3) 0.0390(8) Uani 1 1 d . . . H7 H 0.2977 0.4947 0.6179 0.047 Uiso 1 1 calc R . . C8 C 0.0574(4) 0.5304(3) 0.6426(3) 0.0359(8) Uani 1 1 d . . . C9 C 0.0805(4) 0.4191(4) 0.5704(3) 0.0439(9) Uani 1 1 d . . . H9 H 0.204(4) 0.363(3) 0.544(3) 0.043(9) Uiso 1 1 d . . . C10 C -0.0614(5) 0.4080(4) 0.5526(3) 0.0455(10) Uani 1 1 d . . . H10A H -0.073(3) 0.319(3) 0.612(2) 0.055 Uiso 1 1 d . . . H10B H -0.045(3) 0.382(3) 0.471(3) 0.055 Uiso 1 1 d . . . C11 C -0.4096(4) 0.9966(4) 0.5263(3) 0.0702(11) Uani 1 1 d . . . H11A H -0.3591 0.9166 0.5836 0.084 Uiso 1 1 calc R . . H11B H -0.5180 1.0079 0.5322 0.084 Uiso 1 1 calc R . . C12 C -0.4226(5) 1.1434(4) 0.5524(3) 0.0707(11) Uani 1 1 d . . . H12A H -0.5284 1.2053 0.6042 0.085 Uiso 1 1 calc R . . H12B H -0.3364 1.1257 0.5907 0.085 Uiso 1 1 calc R . . C13 C -0.4045(5) 1.2193(4) 0.4350(3) 0.0829(13) Uani 1 1 d . . . H13A H -0.3298 1.2625 0.4268 0.099 Uiso 1 1 calc R . . H13B H -0.5099 1.3025 0.4243 0.099 Uiso 1 1 calc R . . C14 C -0.3364(5) 1.0960(5) 0.3429(3) 0.0915(13) Uani 1 1 d . . . H14A H -0.4128 1.1221 0.2927 0.110 Uiso 1 1 calc R . . H14B H -0.2326 1.0856 0.2923 0.110 Uiso 1 1 calc R . . C15 C 0.0562(4) 0.9737(4) 0.4849(3) 0.0564(10) Uani 1 1 d . . . H15A H 0.0128 0.9334 0.5599 0.068 Uiso 1 1 calc R . . H15B H -0.0255 1.0785 0.4712 0.068 Uiso 1 1 calc R . . C16 C 0.2108(4) 0.9724(4) 0.4897(3) 0.0659(10) Uani 1 1 d . . . H16A H 0.1932 1.0766 0.4966 0.079 Uiso 1 1 calc R . . H16B H 0.2531 0.9091 0.5571 0.079 Uiso 1 1 calc R . . C17 C 0.3254(5) 0.9050(5) 0.3743(4) 0.0855(13) Uani 1 1 d . . . H17A H 0.3342 0.9853 0.3174 0.103 Uiso 1 1 calc R . . H17B H 0.4339 0.8311 0.3862 0.103 Uiso 1 1 calc R . . C18 C 0.2557(7) 0.8339(7) 0.3358(5) 0.210(4) Uani 1 1 d . . . H18A H 0.3171 0.7229 0.3489 0.252 Uiso 1 1 calc R . . H18B H 0.2650 0.8535 0.2501 0.252 Uiso 1 1 calc R . . C19 C -0.3878(4) 0.5975(4) 0.0499(3) 0.0630(10) Uani 1 1 d . . . H19A H -0.3930 0.6688 -0.0173 0.095 Uiso 1 1 calc R . . H19B H -0.4756 0.6498 0.1167 0.095 Uiso 1 1 calc R . . H19C H -0.3982 0.5128 0.0290 0.095 Uiso 1 1 calc R . . C20 C -0.2189(4) 0.6629(4) 0.1241(3) 0.0492(10) Uani 1 1 d . . . H20A H -0.240(3) 0.751(3) 0.052(2) 0.059 Uiso 1 1 d . . . H20B H -0.315(3) 0.719(3) 0.192(2) 0.059 Uiso 1 1 d . . . C21 C -0.0491(4) 0.5963(3) 0.1505(2) 0.0382(8) Uani 1 1 d . . . C22 C 0.0380(5) 0.6723(4) 0.1183(3) 0.0532(11) Uani 1 1 d . . . H22 H -0.0057 0.7686 0.0794 0.064 Uiso 1 1 calc R . . C23 C 0.1941(4) 0.6124(4) 0.1408(3) 0.0500(9) Uani 1 1 d . . . H23 H 0.2539 0.6677 0.1162 0.060 Uiso 1 1 calc R . . C24 C 0.2587(4) 0.4706(5) 0.1998(3) 0.0516(11) Uani 1 1 d . . . H24 H 0.3611 0.4311 0.2173 0.062 Uiso 1 1 calc R . . C25 C 0.1715(4) 0.3874(4) 0.2329(3) 0.0522(9) Uani 1 1 d . . . H25 H 0.2140 0.2945 0.2761 0.063 Uiso 1 1 calc R . . C26 C 0.0137(4) 0.4410(4) 0.2019(3) 0.0315(8) Uani 1 1 d . . . C27 C -0.0685(5) 0.3575(4) 0.2190(3) 0.0582(10) Uani 1 1 d . . . H27 H -0.009(4) 0.246(4) 0.263(3) 0.103(13) Uiso 1 1 d . . . C28 C -0.2208(5) 0.4172(4) 0.1769(3) 0.0564(10) Uani 1 1 d . . . H28A H -0.218(3) 0.328(3) 0.108(2) 0.068 Uiso 1 1 d . . . H28B H -0.319(3) 0.472(3) 0.250(3) 0.068 Uiso 1 1 d . . . C29 C 0.4979(4) 0.3218(4) -0.1372(3) 0.0617(10) Uani 1 1 d . . . H29A H 0.4526 0.4166 -0.0947 0.074 Uiso 1 1 calc R . . H29B H 0.5035 0.3475 -0.2219 0.074 Uiso 1 1 calc R . . C30 C 0.6640(4) 0.2123(4) -0.1169(3) 0.0596(10) Uani 1 1 d . . . H30A H 0.7284 0.1381 -0.1803 0.072 Uiso 1 1 calc R . . H30B H 0.7233 0.2664 -0.1100 0.072 Uiso 1 1 calc R . . C31 C 0.6207(4) 0.1356(4) 0.0003(3) 0.0591(10) Uani 1 1 d . . . H31A H 0.5955 0.1974 0.0675 0.071 Uiso 1 1 calc R . . H31B H 0.7097 0.0332 0.0096 0.071 Uiso 1 1 calc R . . C32 C 0.4726(4) 0.1263(3) -0.0092(3) 0.0543(9) Uani 1 1 d . . . H32A H 0.5040 0.0255 -0.0370 0.065 Uiso 1 1 calc R . . H32B H 0.3962 0.1420 0.0683 0.065 Uiso 1 1 calc R . . C33 C 0.0815(4) 0.0627(4) -0.0090(3) 0.0558(9) Uani 1 1 d . . . H33A H -0.0068 0.0345 0.0188 0.067 Uiso 1 1 calc R . . H33B H 0.0959 0.0974 0.0586 0.067 Uiso 1 1 calc R . . C34 C 0.2401(4) -0.0755(3) -0.0655(3) 0.0529(9) Uani 1 1 d . . . H34A H 0.3255 -0.1024 -0.0235 0.063 Uiso 1 1 calc R . . H34B H 0.2226 -0.1650 -0.0640 0.063 Uiso 1 1 calc R . . C35 C 0.2858(4) -0.0222(3) -0.1921(3) 0.0478(9) Uani 1 1 d . . . H35A H 0.3663 0.0140 -0.2004 0.057 Uiso 1 1 calc R . . H35B H 0.3293 -0.1047 -0.2477 0.057 Uiso 1 1 calc R . . C36 C 0.1256(4) 0.1077(3) -0.2124(3) 0.0466(8) Uani 1 1 d . . . H36A H 0.1435 0.1794 -0.2747 0.056 Uiso 1 1 calc R . . H36B H 0.0616 0.0683 -0.2351 0.056 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 C1 0.056(2) 0.082(3) 0.062(2) 0.0026(19) -0.0209(19) -0.044(2) K1 0.0505(5) 0.0393(4) 0.0355(5) -0.0033(4) -0.0069(4) -0.0229(4) N1 0.0385(16) 0.0453(17) 0.0362(16) -0.0007(12) -0.0119(12) -0.0205(14) O1 0.0659(16) 0.0436(14) 0.0489(16) -0.0041(12) -0.0026(13) -0.0155(12) C2 0.049(2) 0.050(2) 0.034(2) -0.0012(17) 0.0005(17) -0.0240(19) K2 0.0334(4) 0.0353(4) 0.0370(5) -0.0056(3) -0.0041(3) -0.0129(4) N2 0.0359(16) 0.0410(16) 0.0395(16) -0.0071(13) -0.0042(12) -0.0172(13) O2 0.0651(19) 0.104(2) 0.0792(19) -0.0448(16) 0.0092(16) -0.0587(17) C3 0.037(2) 0.0318(18) 0.0157(17) 0.0000(13) -0.0047(14) -0.0155(16) O3 0.0380(14) 0.0590(16) 0.0606(15) -0.0053(13) -0.0133(12) -0.0199(12) C4 0.049(2) 0.038(2) 0.040(2) 0.0027(16) -0.0120(18) -0.014(2) O4 0.0533(15) 0.0377(13) 0.0520(15) -0.0072(12) -0.0104(13) -0.0212(12) C5 0.063(3) 0.046(2) 0.052(2) -0.0037(18) -0.019(2) -0.028(2) C6 0.044(2) 0.051(2) 0.053(3) 0.0040(19) -0.0131(19) -0.029(2) C7 0.045(2) 0.036(2) 0.033(2) 0.0032(15) -0.0113(16) -0.0156(17) C8 0.051(3) 0.029(2) 0.0260(19) -0.0009(15) -0.0086(18) -0.017(2) C9 0.040(2) 0.039(2) 0.042(2) 0.0006(16) -0.0090(18) -0.0106(19) C10 0.054(3) 0.047(2) 0.045(2) -0.0052(19) -0.017(2) -0.027(2) C11 0.073(3) 0.053(2) 0.079(3) -0.002(2) -0.002(2) -0.032(2) C12 0.061(3) 0.071(3) 0.073(3) 0.003(2) -0.010(2) -0.028(2) C13 0.087(3) 0.059(3) 0.081(3) 0.012(2) -0.004(2) -0.029(2) C14 0.111(4) 0.083(3) 0.055(3) 0.014(3) -0.024(2) -0.028(3) C15 0.047(2) 0.060(2) 0.053(2) -0.0030(19) -0.0081(18) -0.019(2) C16 0.052(2) 0.080(3) 0.061(3) -0.031(2) -0.0019(19) -0.024(2) C17 0.062(3) 0.112(3) 0.086(3) -0.037(3) 0.000(2) -0.042(3) C18 0.132(5) 0.341(9) 0.219(7) -0.231(7) 0.104(5) -0.169(6) C19 0.045(2) 0.092(3) 0.063(2) -0.026(2) -0.0007(18) -0.040(2) C20 0.031(2) 0.056(3) 0.057(3) -0.025(2) -0.002(2) -0.015(2) C21 0.051(2) 0.047(2) 0.0231(18) -0.0128(15) 0.0043(17) -0.031(2) C22 0.062(3) 0.059(3) 0.038(2) -0.007(2) -0.005(2) -0.029(2) C23 0.037(2) 0.070(3) 0.046(2) -0.016(2) -0.0043(17) -0.026(2) C24 0.048(3) 0.070(3) 0.042(2) -0.017(2) 0.000(2) -0.031(2) C25 0.061(3) 0.051(2) 0.032(2) -0.0129(16) -0.0038(18) -0.016(2) C26 0.038(2) 0.033(2) 0.029(2) -0.0063(16) -0.0040(17) -0.0213(18) C27 0.076(3) 0.059(3) 0.045(2) -0.0033(19) -0.009(2) -0.037(2) C28 0.058(3) 0.071(3) 0.041(2) -0.010(2) -0.0007(19) -0.034(2) C29 0.053(2) 0.069(3) 0.059(2) 0.0034(19) -0.0138(19) -0.026(2) C30 0.045(2) 0.051(2) 0.088(3) -0.004(2) -0.020(2) -0.024(2) C31 0.053(2) 0.053(2) 0.073(3) -0.006(2) -0.033(2) -0.0157(19) C32 0.053(2) 0.046(2) 0.059(2) -0.0124(18) -0.0086(19) -0.0181(18) C33 0.072(3) 0.060(2) 0.037(2) 0.0034(19) -0.0035(18) -0.038(2) C34 0.057(2) 0.050(2) 0.063(2) 0.0195(18) -0.0289(19) -0.031(2) C35 0.046(2) 0.049(2) 0.052(2) -0.0051(17) -0.0095(17) -0.0242(19) C36 0.070(3) 0.045(2) 0.036(2) 0.0040(16) -0.0203(18) -0.033(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 N1 1.456(3) . ? K1 O1 2.691(2) . ? K1 O2 2.691(2) . ? K1 N1 2.863(2) . ? K1 C9 3.006(3) . ? K1 C22 3.119(3) . ? K1 C23 3.110(3) . ? K1 C24 3.138(3) . ? K1 C8 3.165(3) . ? K1 C21 3.178(3) . ? K1 C25 3.210(3) . ? K1 C26 3.357(3) . ? K1 C3 3.474(3) . ? N1 C2 1.470(4) . ? N1 C10 1.464(4) . ? O1 C11 1.392(4) . ? O1 C14 1.432(4) . ? C2 C3 1.515(4) . ? K2 O4 2.695(2) . ? K2 O3 2.708(2) . ? K2 N2 2.819(2) . ? K2 C21 3.002(3) . ? K2 C6 3.150(3) 1_554 ? K2 C7 3.171(3) 1_554 ? K2 C5 3.177(3) 1_554 ? K2 C4 3.202(3) 1_554 ? K2 C26 3.197(3) . ? K2 C3 3.216(3) 1_554 ? K2 C8 3.207(3) 1_554 ? K2 C27 3.504(4) . ? N2 C20 1.451(4) . ? N2 C28 1.478(4) . ? N2 C19 1.452(3) . ? O2 C18 1.367(5) . ? O2 C15 1.398(3) . ? C3 C4 1.369(4) . ? C3 C8 1.428(4) . ? C3 K2 3.216(3) 1_556 ? O3 C29 1.423(4) . ? O3 C32 1.432(3) . ? C4 C5 1.351(4) . ? C4 K2 3.202(3) 1_556 ? O4 C33 1.418(3) . ? O4 C36 1.433(3) . ? C5 C6 1.384(4) . ? C5 K2 3.177(3) 1_556 ? C6 C7 1.372(4) . ? C6 K2 3.150(3) 1_556 ? C7 C8 1.460(5) . ? C7 K2 3.171(3) 1_556 ? C8 C9 1.381(4) . ? C8 K2 3.207(3) 1_556 ? C9 C10 1.480(5) . ? C11 C12 1.464(4) . ? C12 C13 1.458(4) . ? C13 C14 1.518(5) . ? C15 C16 1.486(4) . ? C16 C17 1.487(4) . ? C17 C18 1.358(5) . ? C20 C21 1.528(4) . ? C21 C22 1.317(4) . ? C21 C26 1.443(4) . ? C22 C23 1.398(4) . ? C23 C24 1.380(4) . ? C24 C25 1.378(4) . ? C25 C26 1.464(4) . ? C26 C27 1.349(4) . ? C27 C28 1.473(5) . ? C29 C30 1.486(4) . ? C30 C31 1.505(4) . ? C31 C32 1.494(4) . ? C33 C34 1.525(4) . ? C34 C35 1.501(4) . ? C35 C36 1.499(4) . ? 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 K1 O2 82.34(8) . . ? O1 K1 N1 88.39(7) . . ? O2 K1 N1 137.16(8) . . ? O1 K1 C9 132.05(9) . . ? O2 K1 C9 112.54(9) . . ? N1 K1 C9 48.96(9) . . ? O1 K1 C22 94.54(9) . . ? O2 K1 C22 95.06(10) . . ? N1 K1 C22 127.43(9) . . ? C9 K1 C22 126.88(10) . . ? O1 K1 C23 115.00(9) . . ? O2 K1 C23 82.44(8) . . ? N1 K1 C23 138.15(8) . . ? C9 K1 C23 112.11(10) . . ? C22 K1 C23 25.94(8) . . ? O1 K1 C24 139.27(9) . . ? O2 K1 C24 94.53(9) . . ? N1 K1 C24 118.25(9) . . ? C9 K1 C24 86.73(10) . . ? C22 K1 C24 45.07(10) . . ? C23 K1 C24 25.52(8) . . ? O1 K1 C8 115.98(7) . . ? O2 K1 C8 92.56(9) . . ? N1 K1 C8 54.70(8) . . ? C9 K1 C8 25.70(8) . . ? C22 K1 C8 149.28(9) . . ? C23 K1 C8 127.50(9) . . ? C24 K1 C8 104.71(9) . . ? O1 K1 C21 94.17(7) . . ? O2 K1 C21 118.97(8) . . ? N1 K1 C21 103.32(8) . . ? C9 K1 C21 113.87(9) . . ? C22 K1 C21 24.11(8) . . ? C23 K1 C21 44.34(8) . . ? C24 K1 C21 52.05(8) . . ? C8 K1 C21 139.57(8) . . ? O1 K1 C25 138.31(8) . . ? O2 K1 C25 119.41(9) . . ? N1 K1 C25 94.85(8) . . ? C9 K1 C25 75.33(9) . . ? C22 K1 C25 51.56(9) . . ? C23 K1 C25 44.37(8) . . ? C24 K1 C25 25.03(8) . . ? C8 K1 C25 99.16(8) . . ? C21 K1 C25 44.64(8) . . ? O1 K1 C26 113.68(8) . . ? O2 K1 C26 134.44(8) . . ? N1 K1 C26 87.45(8) . . ? C9 K1 C26 88.55(9) . . ? C22 K1 C26 43.81(7) . . ? C23 K1 C26 52.00(8) . . ? C24 K1 C26 44.84(9) . . ? C8 K1 C26 114.25(8) . . ? C21 K1 C26 25.33(7) . . ? C25 K1 C26 25.64(7) . . ? O1 K1 C3 92.20(7) . . ? O2 K1 C3 94.40(8) . . ? N1 K1 C3 44.07(7) . . ? C9 K1 C3 43.49(8) . . ? C22 K1 C3 169.04(9) . . ? C23 K1 C3 151.74(8) . . ? C24 K1 C3 128.50(9) . . ? C8 K1 C3 24.27(7) . . ? C21 K1 C3 146.57(8) . . ? C25 K1 C3 118.43(8) . . ? C26 K1 C3 125.31(8) . . ? C2 N1 C1 111.9(2) . . ? C2 N1 C10 108.8(3) . . ? C1 N1 C10 110.1(3) . . ? C2 N1 K1 112.52(18) . . ? C1 N1 K1 123.38(17) . . ? C10 N1 K1 86.60(19) . . ? C11 O1 C14 107.4(2) . . ? C11 O1 K1 115.25(18) . . ? C14 O1 K1 126.8(2) . . ? N1 C2 C3 109.9(3) . . ? O4 K2 O3 87.83(6) . . ? O4 K2 N2 85.84(7) . . ? O3 K2 N2 140.50(7) . . ? O4 K2 C21 121.20(8) . . ? O3 K2 C21 104.46(7) . . ? N2 K2 C21 48.85(8) . . ? O4 K2 C6 134.46(8) . 1_554 ? O3 K2 C6 91.52(8) . 1_554 ? N2 K2 C6 119.93(8) . 1_554 ? C21 K2 C6 103.01(9) . 1_554 ? O4 K2 C7 109.72(8) . 1_554 ? O3 K2 C7 86.04(8) . 1_554 ? N2 K2 C7 132.59(7) . 1_554 ? C21 K2 C7 128.07(9) . 1_554 ? C6 K2 C7 25.08(7) 1_554 1_554 ? O4 K2 C5 140.06(8) . 1_554 ? O3 K2 C5 114.37(9) . 1_554 ? N2 K2 C5 94.66(8) . 1_554 ? C21 K2 C5 86.46(9) . 1_554 ? C6 K2 C5 25.27(8) 1_554 1_554 ? C7 K2 C5 44.78(8) 1_554 1_554 ? O4 K2 C4 118.14(8) . 1_554 ? O3 K2 C4 134.61(8) . 1_554 ? N2 K2 C4 81.51(8) . 1_554 ? C21 K2 C4 93.19(9) . 1_554 ? C6 K2 C4 43.38(9) 1_554 1_554 ? C7 K2 C4 51.39(8) 1_554 1_554 ? C5 K2 C4 24.46(8) 1_554 1_554 ? O4 K2 C26 99.56(8) . . ? O3 K2 C26 89.18(8) . . ? N2 K2 C26 53.77(8) . . ? C21 K2 C26 26.69(7) . . ? C6 K2 C26 125.98(9) 1_554 . ? C7 K2 C26 150.09(9) 1_554 . ? C5 K2 C26 112.83(8) 1_554 . ? C4 K2 C26 118.92(9) 1_554 . ? O4 K2 C3 96.18(7) . 1_554 ? O3 K2 C3 129.18(7) . 1_554 ? N2 K2 C3 90.28(7) . 1_554 ? C21 K2 C3 115.75(8) . 1_554 ? C6 K2 C3 51.28(8) 1_554 1_554 ? C7 K2 C3 44.96(7) 1_554 1_554 ? C5 K2 C3 43.94(8) 1_554 1_554 ? C4 K2 C3 24.63(7) 1_554 1_554 ? C26 K2 C3 139.02(8) . 1_554 ? O4 K2 C8 90.87(8) . 1_554 ? O3 K2 C8 104.01(7) . 1_554 ? N2 K2 C8 115.03(8) . 1_554 ? C21 K2 C8 137.37(8) . 1_554 ? C6 K2 C8 45.32(9) 1_554 1_554 ? C7 K2 C8 26.46(8) 1_554 1_554 ? C5 K2 C8 52.87(8) 1_554 1_554 ? C4 K2 C8 44.63(8) 1_554 1_554 ? C26 K2 C8 163.54(8) . 1_554 ? C3 K2 C8 25.69(7) 1_554 1_554 ? O4 K2 C27 78.66(8) . . ? O3 K2 C27 96.98(9) . . ? N2 K2 C27 43.57(9) . . ? C21 K2 C27 43.23(8) . . ? C6 K2 C27 146.25(9) 1_554 . ? C7 K2 C27 171.26(8) 1_554 . ? C5 K2 C27 126.96(9) 1_554 . ? C4 K2 C27 122.97(9) 1_554 . ? C26 K2 C27 22.64(7) . . ? C3 K2 C27 133.56(9) 1_554 . ? C8 K2 C27 156.18(9) 1_554 . ? C20 N2 C28 110.8(3) . . ? C20 N2 C19 110.5(2) . . ? C28 N2 C19 107.8(3) . . ? C20 N2 K2 93.87(18) . . ? C28 N2 K2 108.40(18) . . ? C19 N2 K2 124.62(18) . . ? C18 O2 C15 106.9(3) . . ? C18 O2 K1 118.9(3) . . ? C15 O2 K1 124.5(2) . . ? C4 C3 C8 120.9(3) . . ? C4 C3 C2 122.6(3) . . ? C8 C3 C2 116.4(3) . . ? C4 C3 K2 77.12(18) . 1_556 ? C8 C3 K2 76.81(16) . 1_556 ? C2 C3 K2 114.41(19) . 1_556 ? C4 C3 K1 119.89(19) . . ? C8 C3 K1 65.63(15) . . ? C2 C3 K1 85.73(17) . . ? K2 C3 K1 142.35(9) 1_556 . ? C29 O3 C32 108.0(2) . . ? C29 O3 K2 113.32(17) . . ? C32 O3 K2 128.35(18) . . ? C3 C4 C5 123.1(3) . . ? C3 C4 K2 78.25(17) . 1_556 ? C5 C4 K2 76.73(19) . 1_556 ? C33 O4 C36 107.0(2) . . ? C33 O4 K2 119.51(18) . . ? C36 O4 K2 114.62(17) . . ? C6 C5 C4 118.3(3) . . ? C6 C5 K2 76.3(2) . 1_556 ? C4 C5 K2 78.81(19) . 1_556 ? C7 C6 C5 122.6(4) . . ? C7 C6 K2 78.31(18) . 1_556 ? C5 C6 K2 78.5(2) . 1_556 ? C6 C7 C8 119.7(3) . . ? C6 C7 K2 76.61(18) . 1_556 ? C8 C7 K2 78.17(18) . 1_556 ? C9 C8 C3 120.6(3) . . ? C9 C8 C7 123.9(3) . . ? C3 C8 C7 115.5(3) . . ? C9 C8 K1 70.72(19) . . ? C3 C8 K1 90.10(16) . . ? C7 C8 K1 108.4(2) . . ? C9 C8 K2 117.8(2) . 1_556 ? C3 C8 K2 77.50(16) . 1_556 ? C7 C8 K2 75.37(18) . 1_556 ? K1 C8 K2 167.35(10) . 1_556 ? C8 C9 C10 120.7(3) . . ? C8 C9 K1 83.58(19) . . ? C10 C9 K1 81.0(2) . . ? N1 C10 C9 111.6(3) . . ? O1 C11 C12 108.5(3) . . ? C13 C12 C11 103.9(3) . . ? C12 C13 C14 106.7(3) . . ? O1 C14 C13 105.4(3) . . ? O2 C15 C16 107.2(3) . . ? C17 C16 C15 104.2(3) . . ? C18 C17 C16 103.8(3) . . ? C17 C18 O2 114.5(4) . . ? N2 C20 C21 108.2(3) . . ? C22 C21 C26 123.0(3) . . ? C22 C21 C20 121.2(3) . . ? C26 C21 C20 115.6(3) . . ? C22 C21 K2 95.16(19) . . ? C26 C21 K2 84.18(16) . . ? C20 C21 K2 85.33(18) . . ? C22 C21 K1 75.43(19) . . ? C26 C21 K1 84.25(16) . . ? C20 C21 K1 116.92(19) . . ? K2 C21 K1 157.67(11) . . ? C21 C22 C23 121.9(4) . . ? C21 C22 K1 80.46(19) . . ? C23 C22 K1 76.65(19) . . ? C24 C23 C22 119.3(3) . . ? C24 C23 K1 78.38(19) . . ? C22 C23 K1 77.42(19) . . ? C25 C24 C23 120.0(3) . . ? C25 C24 K1 80.44(18) . . ? C23 C24 K1 76.10(19) . . ? C24 C25 C26 122.0(3) . . ? C24 C25 K1 74.53(19) . . ? C26 C25 K1 82.77(17) . . ? C27 C26 C21 121.9(3) . . ? C27 C26 C25 124.9(3) . . ? C21 C26 C25 113.2(3) . . ? C27 C26 K2 91.6(2) . . ? C21 C26 K2 69.13(15) . . ? C25 C26 K2 108.57(19) . . ? C27 C26 K1 125.9(2) . . ? C21 C26 K1 70.41(15) . . ? C25 C26 K1 71.59(16) . . ? K2 C26 K1 135.42(11) . . ? C26 C27 C28 120.9(3) . . ? C26 C27 K2 65.76(18) . . ? C28 C27 K2 80.6(2) . . ? C27 C28 N2 110.9(3) . . ? O3 C29 C30 106.7(3) . . ? C31 C30 C29 100.9(3) . . ? C30 C31 C32 103.3(3) . . ? O3 C32 C31 106.8(3) . . ? O4 C33 C34 106.8(2) . . ? C35 C34 C33 104.7(2) . . ? C36 C35 C34 103.0(2) . . ? O4 C36 C35 104.3(2) . . ? data_strohmann9 _database_code_depnum_ccdc_archive 'CCDC 863582' #TrackingRef 'strohmann-cpd-5k.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H52 K2 N2 O3' _chemical_formula_weight 590.96 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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 3 (1) 2 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' 'y, x, -z' 'x-y, -y, -z+2/3' '-x, -x+y, -z+1/3' _cell_length_a 9.3923(3) _cell_length_b 9.3923(3) _cell_length_c 67.355(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5145.7(3) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description hexagonal _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.144 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 0.307 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.883 _exptl_absorpt_correction_T_max 0.883 _exptl_absorpt_process_details 'CrysAlis Red (Oxford Diffraction 2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 11013 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0828 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -62 _diffrn_reflns_limit_l_max 80 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 24.99 _reflns_number_total 6035 _reflns_number_gt 3234 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2006)' _computing_cell_refinement 'CrysAlis Red (Oxford Diffraction, 2006)' _computing_data_reduction 'CrysAlis Red (Oxford Diffraction, 2006)' _computing_structure_solution 'SHELXS-90 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 V1.073 (Farrugia, 2001)' _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^)+(0.2300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(16) _refine_ls_number_reflns 6035 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1609 _refine_ls_R_factor_gt 0.1111 _refine_ls_wR_factor_ref 0.3522 _refine_ls_wR_factor_gt 0.3274 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.363 _refine_ls_shift/su_mean 0.037 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 C1 C -0.369(3) -0.368(3) 0.0166(3) 0.268(18) Uani 1 1 d . . . H30A H -0.3097 -0.4074 0.0245 0.322 Uiso 1 1 calc R . . H30B H -0.3998 -0.3032 0.0250 0.322 Uiso 1 1 calc R . . C2 C -0.479(4) -0.471(3) 0.0092(4) 0.36(3) Uani 1 1 d . . . H31A H -0.5749 -0.4618 0.0124 0.437 Uiso 1 1 calc R . . H31B H -0.4969 -0.5740 0.0148 0.437 Uiso 1 1 calc R . . C3 C -0.2199(15) 0.1551(19) 0.01215(18) 0.123(5) Uani 1 1 d . . . H18A H -0.2846 0.1955 0.0184 0.184 Uiso 1 1 calc R . . H18B H -0.2658 0.0405 0.0151 0.184 Uiso 1 1 calc R . . H18C H -0.2203 0.1695 -0.0020 0.184 Uiso 1 1 calc R . . C4 C 0.023(2) 0.4174(17) 0.01457(17) 0.122(5) Uani 1 1 d . . . H19A H 0.0067 0.4311 0.0008 0.184 Uiso 1 1 calc R . . H19B H 0.1380 0.4679 0.0173 0.184 Uiso 1 1 calc R . . H19C H -0.0245 0.4683 0.0225 0.184 Uiso 1 1 calc R . . C5 C -0.040(2) 0.212(2) 0.04069(17) 0.124(4) Uani 1 1 d . . . H17A H 0.0717 0.2860 0.0449 0.148 Uiso 1 1 calc R . . H17B H -0.1120 0.2367 0.0485 0.148 Uiso 1 1 calc R . . C6 C -0.0810(13) 0.0411(17) 0.04501(14) 0.097(3) Uani 1 1 d . . . H4 H -0.1884 -0.0370 0.0507 0.116 Uiso 1 1 calc R . . C7 C 0.0433(13) -0.0004(13) 0.04402(11) 0.085(3) Uani 1 1 d . . . C8 C 0.2026(14) 0.1007(14) 0.03764(12) 0.087(3) Uani 1 1 d . . . H15 H 0.2302 0.2043 0.0329 0.105 Uiso 1 1 calc R . . C9 C 0.3201(16) 0.0595(19) 0.03785(15) 0.103(4) Uani 1 1 d . . . H14 H 0.4303 0.1383 0.0330 0.123 Uiso 1 1 calc R . . C10 C 0.288(2) -0.094(3) 0.04436(16) 0.128(5) Uani 1 1 d . . . H13 H 0.3745 -0.1231 0.0449 0.153 Uiso 1 1 calc R . . C11 C 0.129(3) -0.2034(18) 0.04961(15) 0.117(5) Uani 1 1 d . . . H12 H 0.1022 -0.3125 0.0544 0.141 Uiso 1 1 calc R . . C12 C 0.0118(19) -0.1631(16) 0.04928(14) 0.107(4) Uani 1 1 d . . . H11 H -0.1013 -0.2481 0.0524 0.128 Uiso 1 1 calc R . . C13 C 0.409(3) 0.517(2) 0.0684(3) 0.211(11) Uani 1 1 d . . . H29A H 0.4901 0.4838 0.0657 0.253 Uiso 1 1 calc R . . H29B H 0.3527 0.5113 0.0561 0.253 Uiso 1 1 calc R . . C14 C 0.480(2) 0.666(2) 0.0756(3) 0.160(7) Uani 1 1 d . . . H28A H 0.4817 0.7411 0.0657 0.192 Uiso 1 1 calc R . . H28B H 0.5934 0.7004 0.0791 0.192 Uiso 1 1 calc R . . C15 C 0.396(2) 0.671(2) 0.0924(3) 0.165(7) Uani 1 1 d . . . H27A H 0.3427 0.7344 0.0898 0.198 Uiso 1 1 calc R . . H27B H 0.4722 0.7220 0.1034 0.198 Uiso 1 1 calc R . . C16 C 0.280(2) 0.508(2) 0.0971(3) 0.174(8) Uani 1 1 d . . . H26A H 0.3008 0.4802 0.1102 0.208 Uiso 1 1 calc R . . H26B H 0.1701 0.4938 0.0969 0.208 Uiso 1 1 calc R . . C17 C 0.6620(18) 0.244(3) 0.0754(2) 0.189(10) Uani 1 1 d . . . H25A H 0.6176 0.1424 0.0679 0.226 Uiso 1 1 calc R . . H25B H 0.7117 0.3362 0.0663 0.226 Uiso 1 1 calc R . . C18 C 0.771(3) 0.254(4) 0.0890(2) 0.210(12) Uani 1 1 d . . . H24A H 0.8768 0.3507 0.0863 0.252 Uiso 1 1 calc R . . H24B H 0.7846 0.1586 0.0878 0.252 Uiso 1 1 calc R . . C19 C 0.725(2) 0.263(3) 0.1089(2) 0.197(10) Uani 1 1 d . . . H23A H 0.6902 0.1610 0.1160 0.237 Uiso 1 1 calc R . . H23B H 0.8152 0.3525 0.1161 0.237 Uiso 1 1 calc R . . C20 C 0.5947(18) 0.293(2) 0.10612(16) 0.147(6) Uani 1 1 d . . . H22A H 0.5069 0.2291 0.1155 0.176 Uiso 1 1 calc R . . H22B H 0.6315 0.4087 0.1082 0.176 Uiso 1 1 calc R . . C23 C 0.4011(12) 0.1007(13) 0.15298(11) 0.084(3) Uani 1 1 d . . . H8A H 0.5129 0.1216 0.1542 0.100 Uiso 1 1 calc R . . H8B H 0.4063 0.1993 0.1477 0.100 Uiso 1 1 calc R . . C24 C 0.3100(12) -0.0369(13) 0.13860(13) 0.081(3) Uani 1 1 d . . . H7 H 0.3527 -0.1110 0.1358 0.098 Uiso 1 1 calc R . . C25 C 0.1779(10) -0.0549(12) 0.12803(11) 0.072(2) Uani 1 1 d . . . C26 C 0.1167(14) 0.0534(14) 0.12878(11) 0.086(3) Uani 1 1 d . . . H1 H 0.1684 0.1437 0.1372 0.103 Uiso 1 1 calc R . . C27 C -0.0142(15) 0.0353(15) 0.11794(14) 0.095(3) Uani 1 1 d . . . H2 H -0.0551 0.1117 0.1202 0.113 Uiso 1 1 calc R . . C28 C -0.0966(13) -0.0932(16) 0.10479(15) 0.092(3) Uani 1 1 d . . . H3 H -0.2012 -0.1158 0.0989 0.111 Uiso 1 1 calc R . . C30 C 0.0868(13) -0.1880(13) 0.11428(13) 0.083(3) Uani 1 1 d . . . H5 H 0.1189 -0.2721 0.1130 0.100 Uiso 1 1 calc R . . C31 C 0.060(3) -0.498(2) 0.1524(3) 0.205(10) Uani 1 1 d . . . H31C H 0.1768 -0.4209 0.1508 0.245 Uiso 1 1 calc R . . H31D H 0.0055 -0.5042 0.1400 0.245 Uiso 1 1 calc R . . C29A C -0.0437(14) -0.2067(14) 0.10346(12) 0.093(3) Uani 1 1 d . . . H4A H -0.0982 -0.2968 0.0951 0.112 Uiso 1 1 calc R . . K1 K 0.0007(3) 0.0007(3) 0.0000 0.0815(8) Uani 1 2 d S . . K2 K 0.2190(3) 0.0951(3) 0.08239(2) 0.0849(7) Uani 1 1 d . . . K3 K 0.0000 -0.1624(3) 0.1667 0.0689(7) Uani 1 2 d S . . N1 N -0.0572(11) 0.2431(12) 0.01926(13) 0.095(2) Uani 1 1 d . . . O1 O -0.2758(13) -0.2758(13) 0.0000 0.262(15) Uani 1 2 d S . . O2 O 0.2943(13) 0.4106(10) 0.08290(13) 0.140(4) Uani 1 1 d . . . O3 O 0.5398(9) 0.2485(16) 0.08695(10) 0.146(4) Uani 1 1 d . . . O4 O 0.0000 -0.4475(13) 0.1667 0.170(7) Uani 1 2 d S . . N2 N 0.3260(8) 0.0677(8) 0.17293(11) 0.0654(17) Uiso 1 1 d . . . C22 C 0.3530(13) -0.0497(13) 0.18363(16) 0.092(3) Uiso 1 1 d . . . H22C H 0.3091 -0.1499 0.1761 0.138 Uiso 1 1 calc R . . H22D H 0.2991 -0.0717 0.1963 0.138 Uiso 1 1 calc R . . H22E H 0.4688 -0.0056 0.1856 0.138 Uiso 1 1 calc R . . C21 C 0.3969(14) 0.2172(13) 0.18460(17) 0.100(3) Uiso 1 1 d . . . H21A H 0.5063 0.2462 0.1886 0.151 Uiso 1 1 calc R . . H21B H 0.3307 0.2001 0.1962 0.151 Uiso 1 1 calc R . . H21C H 0.4008 0.3046 0.1768 0.151 Uiso 1 1 calc R . . C32 C 0.037(3) -0.649(3) 0.1571(4) 0.225(10) Uiso 1 1 d . . . H32A H 0.1417 -0.6467 0.1575 0.270 Uiso 1 1 calc R . . H32B H -0.0335 -0.7302 0.1475 0.270 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 C1 0.21(2) 0.23(2) 0.088(10) -0.012(13) 0.004(12) -0.096(19) C2 0.36(4) 0.23(3) 0.24(3) -0.11(2) 0.20(3) -0.05(3) C3 0.110(10) 0.199(14) 0.079(7) 0.043(8) 0.017(7) 0.091(10) C4 0.203(14) 0.134(11) 0.065(6) 0.013(7) 0.024(8) 0.110(11) C5 0.142(11) 0.185(14) 0.068(7) 0.016(8) 0.021(7) 0.100(10) C6 0.071(6) 0.146(11) 0.051(5) 0.016(6) 0.021(4) 0.038(7) C7 0.098(8) 0.089(7) 0.033(3) 0.014(4) -0.006(4) 0.021(6) C8 0.102(8) 0.098(7) 0.042(4) 0.013(5) 0.010(5) 0.035(7) C9 0.123(10) 0.140(11) 0.051(5) 0.000(6) -0.009(6) 0.071(9) C10 0.155(13) 0.229(18) 0.039(5) -0.027(8) -0.018(7) 0.126(14) C11 0.190(16) 0.135(11) 0.038(5) -0.016(6) -0.024(8) 0.090(13) C12 0.124(10) 0.099(9) 0.046(5) -0.010(5) 0.003(6) 0.016(7) C13 0.25(2) 0.087(10) 0.181(18) -0.005(11) 0.116(17) -0.006(12) C14 0.129(11) 0.128(14) 0.188(18) 0.054(13) 0.039(13) 0.038(10) C15 0.153(13) 0.126(13) 0.188(17) -0.027(11) 0.071(13) 0.049(11) C16 0.214(19) 0.136(13) 0.147(14) -0.009(11) 0.075(14) 0.069(14) C17 0.115(10) 0.36(3) 0.103(10) -0.092(14) -0.015(8) 0.125(15) C18 0.26(2) 0.43(4) 0.076(8) 0.003(15) 0.012(12) 0.28(3) C19 0.160(14) 0.38(3) 0.102(11) 0.005(15) -0.015(10) 0.176(19) C20 0.136(10) 0.235(17) 0.056(6) -0.041(9) -0.010(7) 0.082(12) C23 0.076(6) 0.117(7) 0.042(4) -0.004(5) 0.009(4) 0.037(5) C24 0.086(6) 0.115(7) 0.055(5) 0.003(5) -0.005(5) 0.059(6) C25 0.067(5) 0.088(6) 0.036(4) 0.013(4) 0.010(4) 0.020(5) C26 0.122(8) 0.109(7) 0.036(4) -0.012(5) -0.005(4) 0.065(7) C27 0.125(9) 0.128(9) 0.053(5) 0.036(6) 0.020(6) 0.080(7) C28 0.081(6) 0.121(9) 0.066(6) 0.037(6) 0.016(5) 0.043(7) C30 0.113(8) 0.100(7) 0.046(4) 0.006(5) 0.003(5) 0.061(7) C31 0.30(3) 0.143(15) 0.124(13) 0.059(12) 0.065(16) 0.077(18) C29A 0.118(8) 0.099(7) 0.037(4) 0.014(4) 0.000(5) 0.034(7) K1 0.0870(12) 0.0870(12) 0.0410(11) 0.0026(7) -0.0026(7) 0.0213(15) K2 0.0844(13) 0.1061(16) 0.0387(8) 0.0051(10) 0.0046(9) 0.0286(12) K3 0.0705(16) 0.0791(13) 0.0544(13) 0.0035(6) 0.0070(12) 0.0352(8) N1 0.080(6) 0.122(7) 0.084(6) 0.011(5) 0.013(5) 0.052(5) O1 0.208(11) 0.208(11) 0.074(8) 0.016(8) -0.016(8) -0.119(15) O2 0.190(9) 0.089(5) 0.094(6) 0.005(5) 0.053(6) 0.034(5) O3 0.088(5) 0.280(13) 0.052(4) -0.028(6) 0.006(4) 0.077(7) O4 0.24(2) 0.116(7) 0.193(19) 0.027(8) 0.053(15) 0.122(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 C1 C2 1.12(3) . ? C1 O1 1.417(18) . ? C1 C2 2.01(3) 4 ? C2 C2 1.25(5) 4 ? C2 C1 2.01(3) 4 ? C3 N1 1.409(15) . ? C4 N1 1.455(16) . ? C5 C6 1.479(18) . ? C5 N1 1.497(15) . ? C5 K1 3.515(13) . ? C6 C7 1.405(16) . ? C6 K1 3.196(9) . ? C7 C8 1.380(14) . ? C7 C12 1.448(18) . ? C7 K2 2.954(8) . ? C7 K1 2.992(7) . ? C8 C9 1.340(16) . ? C8 K2 3.020(8) . ? C9 C10 1.39(2) . ? C9 K2 3.214(11) . ? C10 C11 1.37(2) . ? C10 K2 3.358(12) . ? C11 C12 1.332(19) . ? C11 K2 3.329(12) . ? C12 K2 3.150(11) . ? C13 C14 1.31(2) . ? C13 O2 1.426(16) . ? C14 C15 1.39(2) . ? C15 C16 1.40(2) . ? C16 O2 1.380(17) . ? C17 C18 1.34(2) . ? C17 O3 1.404(15) . ? C18 C19 1.42(2) . ? C19 C20 1.40(2) . ? C20 O3 1.376(12) . ? C23 N2 1.476(10) . ? C23 C24 1.495(13) . ? C23 K3 3.441(9) . ? C24 C25 1.365(12) . ? C24 K3 3.164(9) . ? C25 C26 1.398(14) . ? C25 C30 1.444(14) . ? C25 K3 2.982(7) . ? C25 K2 3.323(8) . ? C26 C27 1.365(15) . ? C26 K3 3.098(9) . ? C26 K2 3.235(8) . ? C27 C28 1.380(16) . ? C27 K2 3.101(10) . ? C28 C29A 1.386(16) . ? C28 K2 2.991(9) . ? C30 C29A 1.360(15) . ? C30 K2 3.150(9) . ? C31 O4 1.32(2) . ? C31 C32 1.36(2) . ? C29A K2 3.024(9) . ? K1 O1 2.597(12) . ? K1 N1 2.898(9) . ? K1 N1 2.898(9) 4 ? K1 C7 2.992(7) 4 ? K1 C8 3.021(9) 4 ? K1 C3 3.174(14) 4 ? K1 C6 3.196(9) 4 ? K1 C5 3.515(13) 4 ? K2 O3 2.629(8) . ? K2 O2 2.680(9) . ? K3 O4 2.678(13) . ? K3 N2 2.758(7) . ? K3 N2 2.758(7) 6 ? K3 C25 2.982(7) 6 ? K3 C26 3.098(9) 6 ? K3 C22 3.148(11) 6 ? K3 C24 3.164(9) 6 ? K3 C23 3.441(9) 6 ? O1 C1 1.417(18) 4 ? O4 C31 1.32(2) 6 ? N2 C22 1.441(12) . ? N2 C21 1.449(13) . ? C32 C32 1.42(4) 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 C2 C1 O1 101(2) . . ? C2 C1 C2 34.0(15) . 4 ? O1 C1 C2 67.8(12) . 4 ? C1 C2 C2 115.9(15) . 4 ? C1 C2 C1 86.2(18) . 4 ? C2 C2 C1 30.2(10) 4 4 ? C6 C5 N1 114.0(11) . . ? C6 C5 K1 65.4(6) . . ? N1 C5 K1 53.9(6) . . ? C7 C6 C5 119.5(11) . . ? C7 C6 K1 68.9(5) . . ? C5 C6 K1 89.7(6) . . ? C8 C7 C6 126.1(11) . . ? C8 C7 C12 112.4(12) . . ? C6 C7 C12 121.4(11) . . ? C8 C7 K2 79.3(5) . . ? C6 C7 K2 106.8(7) . . ? C12 C7 K2 83.9(6) . . ? C8 C7 K1 77.9(5) . . ? C6 C7 K1 85.1(5) . . ? C12 C7 K1 106.8(6) . . ? K2 C7 K1 157.1(4) . . ? C9 C8 C7 124.4(12) . . ? C9 C8 K2 85.9(6) . . ? C7 C8 K2 74.0(4) . . ? C8 C9 C10 121.4(13) . . ? C8 C9 K2 69.6(6) . . ? C10 C9 K2 83.7(7) . . ? C11 C10 C9 116.8(14) . . ? C11 C10 K2 77.0(7) . . ? C9 C10 K2 72.0(7) . . ? C12 C11 C10 121.9(15) . . ? C12 C11 K2 70.7(7) . . ? C10 C11 K2 79.4(8) . . ? C11 C12 C7 122.8(12) . . ? C11 C12 K2 85.8(8) . . ? C7 C12 K2 68.9(5) . . ? C14 C13 O2 107.2(14) . . ? C13 C14 C15 110.1(14) . . ? C14 C15 C16 106.9(15) . . ? O2 C16 C15 106.7(13) . . ? C18 C17 O3 103.0(12) . . ? C17 C18 C19 113.9(15) . . ? C20 C19 C18 101.9(13) . . ? O3 C20 C19 107.3(13) . . ? N2 C23 C24 113.7(8) . . ? N2 C23 K3 50.9(4) . . ? C24 C23 K3 66.7(5) . . ? C25 C24 C23 122.5(9) . . ? C25 C24 K3 69.8(5) . . ? C23 C24 K3 87.6(5) . . ? C24 C25 C26 124.8(9) . . ? C24 C25 C30 123.4(10) . . ? C26 C25 C30 111.9(9) . . ? C24 C25 K3 84.7(5) . . ? C26 C25 K3 81.4(5) . . ? C30 C25 K3 106.1(5) . . ? C24 C25 K2 121.6(5) . . ? C26 C25 K2 74.2(5) . . ? C30 C25 K2 70.5(5) . . ? K3 C25 K2 151.3(4) . . ? C27 C26 C25 124.2(10) . . ? C27 C26 K3 110.9(7) . . ? C25 C26 K3 72.1(5) . . ? C27 C26 K2 72.1(5) . . ? C25 C26 K2 81.2(5) . . ? K3 C26 K2 149.4(4) . . ? C26 C27 C28 121.9(10) . . ? C26 C27 K2 83.1(6) . . ? C28 C27 K2 72.5(5) . . ? C27 C28 C29A 117.0(10) . . ? C27 C28 K2 81.4(6) . . ? C29A C28 K2 78.0(6) . . ? C29A C30 C25 124.1(10) . . ? C29A C30 K2 72.1(5) . . ? C25 C30 K2 83.9(5) . . ? O4 C31 C32 109.4(17) . . ? C30 C29A C28 120.8(10) . . ? C30 C29A K2 82.5(6) . . ? C28 C29A K2 75.4(5) . . ? O1 K1 N1 107.40(19) . . ? O1 K1 N1 107.38(19) . 4 ? N1 K1 N1 145.2(4) . 4 ? O1 K1 C7 93.7(2) . . ? N1 K1 C7 68.7(3) . . ? N1 K1 C7 108.9(3) 4 . ? O1 K1 C7 93.7(2) . 4 ? N1 K1 C7 108.9(3) . 4 ? N1 K1 C7 68.7(3) 4 4 ? C7 K1 C7 172.5(4) . 4 ? O1 K1 C8 118.0(2) . 4 ? N1 K1 C8 90.2(3) . 4 ? N1 K1 C8 73.5(3) 4 4 ? C7 K1 C8 146.5(3) . 4 ? C7 K1 C8 26.5(3) 4 4 ? O1 K1 C3 84.4(3) . 4 ? N1 K1 C3 162.7(3) . 4 ? N1 K1 C3 26.3(3) 4 4 ? C7 K1 C3 98.5(3) . 4 ? C7 K1 C3 82.2(3) 4 4 ? C8 K1 C3 95.4(3) 4 4 ? O1 K1 C6 86.5(2) . 4 ? N1 K1 C6 134.8(3) . 4 ? N1 K1 C6 48.1(3) 4 4 ? C7 K1 C6 155.1(3) . 4 ? C7 K1 C6 26.0(3) 4 4 ? C8 K1 C6 47.0(3) 4 4 ? C3 K1 C6 56.7(3) 4 4 ? O1 K1 C6 86.5(2) . . ? N1 K1 C6 48.1(3) . . ? N1 K1 C6 134.8(3) 4 . ? C7 K1 C6 26.0(3) . . ? C7 K1 C6 155.1(3) 4 . ? C8 K1 C6 137.7(3) 4 . ? C3 K1 C6 122.5(3) 4 . ? C6 K1 C6 173.0(4) 4 . ? O1 K1 C5 103.1(3) . . ? N1 K1 C5 24.7(3) . . ? N1 K1 C5 140.6(3) 4 . ? C7 K1 C5 44.1(3) . . ? C7 K1 C5 133.5(3) 4 . ? C8 K1 C5 112.8(3) 4 . ? C3 K1 C5 141.6(3) 4 . ? C6 K1 C5 159.2(3) 4 . ? C6 K1 C5 24.9(3) . . ? O1 K1 C5 103.1(3) . 4 ? N1 K1 C5 140.6(3) . 4 ? N1 K1 C5 24.7(3) 4 4 ? C7 K1 C5 133.5(3) . 4 ? C7 K1 C5 44.1(3) 4 4 ? C8 K1 C5 53.1(3) 4 4 ? C3 K1 C5 42.3(3) 4 4 ? C6 K1 C5 24.9(3) 4 4 ? C6 K1 C5 159.2(3) . 4 ? C5 K1 C5 153.8(6) . 4 ? O3 K2 O2 78.2(4) . . ? O3 K2 C7 125.6(3) . . ? O2 K2 C7 98.4(3) . . ? O3 K2 C28 142.2(3) . . ? O2 K2 C28 106.4(3) . . ? C7 K2 C28 91.4(3) . . ? O3 K2 C8 99.3(3) . . ? O2 K2 C8 88.9(3) . . ? C7 K2 C8 26.7(3) . . ? C28 K2 C8 118.0(3) . . ? O3 K2 C29A 129.3(4) . . ? O2 K2 C29A 132.1(3) . . ? C7 K2 C29A 93.2(3) . . ? C28 K2 C29A 26.6(3) . . ? C8 K2 C29A 117.4(3) . . ? O3 K2 C27 121.4(3) . . ? O2 K2 C27 87.9(3) . . ? C7 K2 C27 112.6(3) . . ? C28 K2 C27 26.1(3) . . ? C8 K2 C27 137.4(3) . . ? C29A K2 C27 45.3(3) . . ? O3 K2 C12 127.1(4) . . ? O2 K2 C12 125.5(4) . . ? C7 K2 C12 27.2(3) . . ? C28 K2 C12 81.6(3) . . ? C8 K2 C12 44.7(3) . . ? C29A K2 C12 73.2(3) . . ? C27 K2 C12 107.4(4) . . ? O3 K2 C30 104.1(3) . . ? O2 K2 C30 134.4(3) . . ? C7 K2 C30 114.6(3) . . ? C28 K2 C30 45.7(3) . . ? C8 K2 C30 133.9(3) . . ? C29A K2 C30 25.3(3) . . ? C27 K2 C30 51.4(3) . . ? C12 K2 C30 90.1(3) . . ? O3 K2 C9 81.3(3) . . ? O2 K2 C9 101.4(3) . . ? C7 K2 C9 45.7(3) . . ? C28 K2 C9 131.8(4) . . ? C8 K2 C9 24.6(3) . . ? C29A K2 C9 119.1(3) . . ? C27 K2 C9 157.0(3) . . ? C12 K2 C9 50.2(3) . . ? C30 K2 C9 124.1(4) . . ? O3 K2 C26 98.2(2) . . ? O2 K2 C26 91.1(3) . . ? C7 K2 C26 136.2(3) . . ? C28 K2 C26 45.1(3) . . ? C8 K2 C26 162.1(3) . . ? C29A K2 C26 51.6(3) . . ? C27 K2 C26 24.8(3) . . ? C12 K2 C26 124.0(3) . . ? C30 K2 C26 43.2(3) . . ? C9 K2 C26 167.0(4) . . ? O3 K2 C25 89.0(2) . . ? O2 K2 C25 111.5(3) . . ? C7 K2 C25 138.8(2) . . ? C28 K2 C25 54.0(3) . . ? C8 K2 C25 159.2(3) . . ? C29A K2 C25 45.6(2) . . ? C27 K2 C25 44.5(2) . . ? C12 K2 C25 115.6(3) . . ? C30 K2 C25 25.6(2) . . ? C9 K2 C25 142.9(3) . . ? C26 K2 C25 24.6(3) . . ? O4 K3 N2 103.20(15) . . ? O4 K3 N2 103.20(15) . 6 ? N2 K3 N2 153.6(3) . 6 ? O4 K3 C25 93.3(2) . 6 ? N2 K3 C25 108.6(2) . 6 ? N2 K3 C25 69.7(2) 6 6 ? O4 K3 C25 93.3(2) . . ? N2 K3 C25 69.7(2) . . ? N2 K3 C25 108.6(2) 6 . ? C25 K3 C25 173.3(4) 6 . ? O4 K3 C26 118.5(2) . 6 ? N2 K3 C26 93.4(3) . 6 ? N2 K3 C26 73.9(2) 6 6 ? C25 K3 C26 26.5(3) 6 6 ? C25 K3 C26 147.1(3) . 6 ? O4 K3 C26 118.5(2) . . ? N2 K3 C26 73.9(3) . . ? N2 K3 C26 93.4(3) 6 . ? C25 K3 C26 147.1(3) 6 . ? C25 K3 C26 26.5(3) . . ? C26 K3 C26 123.0(4) 6 . ? O4 K3 C22 79.0(2) . 6 ? N2 K3 C22 167.4(2) . 6 ? N2 K3 C22 27.2(2) 6 6 ? C25 K3 C22 83.4(3) 6 6 ? C25 K3 C22 97.9(3) . 6 ? C26 K3 C22 96.3(3) 6 6 ? C26 K3 C22 94.1(3) . 6 ? O4 K3 C24 84.98(19) . 6 ? N2 K3 C24 134.0(2) . 6 ? N2 K3 C24 49.1(2) 6 6 ? C25 K3 C24 25.5(2) 6 6 ? C25 K3 C24 155.9(2) . 6 ? C26 K3 C24 46.0(3) 6 6 ? C26 K3 C24 141.1(3) . 6 ? C22 K3 C24 58.2(2) 6 6 ? O4 K3 C24 84.98(19) . . ? N2 K3 C24 49.1(2) . . ? N2 K3 C24 134.0(2) 6 . ? C25 K3 C24 155.9(2) 6 . ? C25 K3 C24 25.5(2) . . ? C26 K3 C24 141.1(3) 6 . ? C26 K3 C24 46.0(3) . . ? C22 K3 C24 119.6(3) 6 . ? C24 K3 C24 170.0(4) 6 . ? O4 K3 C23 99.8(2) . 6 ? N2 K3 C23 146.3(2) . 6 ? N2 K3 C23 24.5(2) 6 6 ? C25 K3 C23 45.3(2) 6 6 ? C25 K3 C23 133.1(2) . 6 ? C26 K3 C23 53.7(3) 6 6 ? C26 K3 C23 115.4(3) . 6 ? C22 K3 C23 42.7(3) 6 6 ? C24 K3 C23 25.7(2) 6 6 ? C24 K3 C23 158.6(2) . 6 ? O4 K3 C23 99.8(2) . . ? N2 K3 C23 24.5(2) . . ? N2 K3 C23 146.3(2) 6 . ? C25 K3 C23 133.1(2) 6 . ? C25 K3 C23 45.3(2) . . ? C26 K3 C23 115.4(3) 6 . ? C26 K3 C23 53.7(3) . . ? C22 K3 C23 143.2(2) 6 . ? C24 K3 C23 158.6(2) 6 . ? C24 K3 C23 25.7(2) . . ? C23 K3 C23 160.4(4) 6 . ? C3 N1 C4 112.6(10) . . ? C3 N1 C5 113.7(10) . . ? C4 N1 C5 112.6(11) . . ? C3 N1 K1 87.8(8) . . ? C4 N1 K1 126.4(7) . . ? C5 N1 K1 101.4(7) . . ? C1 O1 C1 104.3(16) 4 . ? C1 O1 K1 127.8(8) 4 . ? C1 O1 K1 127.8(8) . . ? C16 O2 C13 107.6(11) . . ? C16 O2 K2 133.3(9) . . ? C13 O2 K2 116.9(9) . . ? C20 O3 C17 110.0(10) . . ? C20 O3 K2 115.4(7) . . ? C17 O3 K2 130.5(8) . . ? C31 O4 C31 109.7(17) 6 . ? C31 O4 K3 125.1(9) 6 . ? C31 O4 K3 125.1(9) . . ? C22 N2 C21 107.4(7) . . ? C22 N2 C23 111.5(8) . . ? C21 N2 C23 110.5(7) . . ? C22 N2 K3 91.6(5) . . ? C21 N2 K3 129.4(6) . . ? C23 N2 K3 104.6(5) . . ? C31 C32 C32 105.7(13) . 6 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.566 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.089