# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name 'L. MacGillivray' 'Tomisla Friscic' _publ_contact_author_name 'Prof L MacGillivray' _publ_contact_author_address ; Department of Chemistry University of Iowa 423B Chemistry Bldg Iowa City Iowa 52242-1294 USA ; _publ_contact_author_email LEN-MACGILLIVRAY@UIOWA.EDU _publ_section_title ; Template-switching : a supramolecular strategy for the quantitative gram-scale construction of a molecular target in the solid state ; #------------------------------------------------------------------------- data_2(1)2(2) _database_code_CSD 203760 _audit_creation_date 2003-02-06T09:06:21-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _chemical_formula_sum 'C33 H28 N2 O2' _chemical_formula_weight 484.57 #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5773(15) _cell_length_b 10.951(2) _cell_length_c 15.687(3) _cell_angle_alpha 77.47(3) _cell_angle_beta 87.47(3) _cell_angle_gamma 84.38(3) _cell_volume 1264.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 #----------------------------------------------------------------------------# _exptl_crystal_F_000 512 _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.19 _exptl_crystal_colour yellow _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# _diffrn_measurement_device_type Nonius _diffrn_measurement_method scanning _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0143 _diffrn_reflns_av_unetI/netI 0.0284 _diffrn_reflns_number 6456 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 22.5 _diffrn_reflns_theta_full 22.5 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 3298 _reflns_number_gt 2764 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# _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^)+(0.0776P)^2^+0.1987P] 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_number_reflns 3298 _refine_ls_number_parameters 336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.132 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.144 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.178 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.055 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 -0.10856(17) 0.35710(13) 0.68556(9) 0.0478(4) Uani 1 1 d . . . H1O H -0.1564 0.3595 0.6379 0.057 Uiso 1 1 calc R . . O2 O 0.32554(18) 0.08511(13) 0.56726(8) 0.0464(4) Uani 1 1 d . . . H2O H 0.2647 0.1126 0.5225 0.056 Uiso 1 1 calc R . . N1 N -0.2641(2) 0.36982(17) 0.52731(11) 0.0457(5) Uani 1 1 d . . . N2 N 0.1272(2) 0.17167(17) 0.41782(10) 0.0447(5) Uani 1 1 d . . . C1 C -0.3267(3) 0.2741(2) 0.50188(14) 0.0494(6) Uani 1 1 d . . . H1 H -0.3212 0.1951 0.5418 0.059 Uiso 1 1 calc R . . C2 C -0.3987(3) 0.28233(19) 0.42180(13) 0.0447(5) Uani 1 1 d . . . H2 H -0.4392 0.2102 0.4073 0.054 Uiso 1 1 calc R . . C3 C -0.4119(2) 0.39663(18) 0.36203(12) 0.0352(5) Uani 1 1 d . . . C4 C -0.3457(2) 0.49688(19) 0.38816(12) 0.0400(5) Uani 1 1 d . . . H4 H -0.3502 0.5772 0.3499 0.048 Uiso 1 1 calc R . . C5 C -0.2742(3) 0.4793(2) 0.46917(13) 0.0444(5) Uani 1 1 d . . . H5 H -0.2291 0.5491 0.485 0.053 Uiso 1 1 calc R . . C6 C -0.4930(2) 0.40905(19) 0.27698(12) 0.0379(5) Uani 1 1 d . . . H6 H -0.5041 0.3343 0.257 0.045 Uiso 1 1 calc R . . C7 C -0.5520(2) 0.51759(19) 0.22583(12) 0.0365(5) Uani 1 1 d . . . H7 H -0.5372 0.591 0.2468 0.044 Uiso 1 1 calc R . . C8 C -0.6368(2) 0.53805(18) 0.14127(12) 0.0346(5) Uani 1 1 d . . . C9 C -0.6614(3) 0.44265(18) 0.09763(12) 0.0398(5) Uani 1 1 d . . . H9 H -0.6245 0.358 0.124 0.048 Uiso 1 1 calc R . . C10 C -0.6986(3) 0.66009(19) 0.10074(12) 0.0409(5) Uani 1 1 d . . . H10 H -0.6865 0.7266 0.1295 0.049 Uiso 1 1 calc R . . C11 C -0.2239(3) 0.31296(19) -0.02076(12) 0.0411(5) Uani 1 1 d . . . H11 H -0.1824 0.2287 0.0044 0.049 Uiso 1 1 calc R . . C12 C -0.2048(2) 0.40778(18) 0.02453(12) 0.0349(5) Uani 1 1 d . . . C13 C -0.2616(3) 0.53041(18) -0.01703(12) 0.0404(5) Uani 1 1 d . . . H13 H -0.2468 0.5972 0.0111 0.048 Uiso 1 1 calc R . . C14 C -0.1314(2) 0.38217(19) 0.11212(12) 0.0368(5) Uani 1 1 d . . . H14 H -0.1052 0.4526 0.134 0.044 Uiso 1 1 calc R . . C15 C -0.0982(2) 0.26976(19) 0.16377(12) 0.0376(5) Uani 1 1 d . . . H15 H -0.1252 0.2 0.1414 0.045 Uiso 1 1 calc R . . C16 C -0.0246(2) 0.24118(18) 0.25137(12) 0.0341(5) Uani 1 1 d . . . C17 C 0.0483(3) 0.32865(19) 0.28924(12) 0.0398(5) Uani 1 1 d . . . H17 H 0.0478 0.4139 0.2591 0.048 Uiso 1 1 calc R . . C18 C 0.1207(3) 0.2899(2) 0.37054(13) 0.0451(5) Uani 1 1 d . . . H18 H 0.1695 0.3509 0.395 0.054 Uiso 1 1 calc R . . C19 C 0.0540(3) 0.0894(2) 0.38220(12) 0.0428(5) Uani 1 1 d . . . H19 H 0.054 0.0053 0.4145 0.051 Uiso 1 1 calc R . . C20 C -0.0215(3) 0.11934(19) 0.30142(12) 0.0405(5) Uani 1 1 d . . . H20 H -0.0718 0.0565 0.2796 0.049 Uiso 1 1 calc R . . C21 C 0.2605(2) 0.14188(18) 0.63265(11) 0.0342(5) Uani 1 1 d . . . C22 C 0.1071(2) 0.22277(17) 0.62391(11) 0.0332(5) Uani 1 1 d . . . H22 H 0.0451 0.2407 0.5707 0.04 Uiso 1 1 calc R . . C23 C 0.0429(2) 0.27798(17) 0.69219(12) 0.0337(5) Uani 1 1 d . . . C24 C 0.1350(2) 0.25274(18) 0.76965(12) 0.0369(5) Uani 1 1 d . . . H24 H 0.0939 0.2911 0.8165 0.044 Uiso 1 1 calc R . . C25 C 0.2877(2) 0.17077(18) 0.77757(12) 0.0386(5) Uani 1 1 d . . . H25 H 0.3499 0.1537 0.8307 0.046 Uiso 1 1 calc R . . C26 C 0.3533(2) 0.11248(18) 0.71067(12) 0.0376(5) Uani 1 1 d . . . C27 C 0.5132(3) 0.0163(2) 0.71850(14) 0.0599(7) Uani 1 1 d . . . H27B H 0.4755 -0.0625 0.7069 0.072 Uiso 1 1 calc R . . H27A H 0.6016 0.0474 0.6725 0.072 Uiso 1 1 calc R . . C28 C 0.6024(3) -0.01347(18) 0.80576(12) 0.0392(5) Uani 1 1 d . . . C29 C 0.5360(3) -0.0979(2) 0.87559(14) 0.0482(6) Uani 1 1 d . . . H29 H 0.4322 -0.1364 0.8684 0.058 Uiso 1 1 calc R . . C30 C 0.6167(3) -0.1274(2) 0.95539(14) 0.0504(6) Uani 1 1 d . . . H30 H 0.5676 -0.1848 1.0027 0.06 Uiso 1 1 calc R . . C31 C 0.7667(3) -0.0743(2) 0.96644(15) 0.0538(6) Uani 1 1 d . . . H31 H 0.8241 -0.0957 1.021 0.065 Uiso 1 1 calc R . . C32 C 0.8344(3) 0.0101(2) 0.89863(16) 0.0562(6) Uani 1 1 d . . . H32 H 0.9385 0.0478 0.9063 0.067 Uiso 1 1 calc R . . C33 C 0.7524(3) 0.04085(19) 0.81903(14) 0.0478(6) Uani 1 1 d . . . H33 H 0.8002 0.1004 0.7727 0.057 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0436(8) 0.0591(10) 0.0387(9) -0.0110(7) -0.0120(6) 0.0117(7) O2 0.0504(9) 0.0591(9) 0.0290(8) -0.0125(7) -0.0098(6) 0.0088(7) N1 0.0381(10) 0.0543(12) 0.0412(10) -0.0029(9) -0.0111(8) 0.0011(8) N2 0.0449(10) 0.0600(12) 0.0292(9) -0.0100(9) -0.0063(8) -0.0021(9) C1 0.0487(13) 0.0449(13) 0.0476(13) 0.0067(10) -0.0146(10) -0.0007(10) C2 0.0451(12) 0.0410(12) 0.0466(13) -0.0043(10) -0.0142(10) -0.0022(9) C3 0.0259(9) 0.0442(12) 0.0336(11) -0.0054(9) -0.0028(8) 0.0005(8) C4 0.0411(11) 0.0427(12) 0.0332(11) 0.0001(9) -0.0070(9) -0.0049(9) C5 0.0448(12) 0.0478(13) 0.0403(12) -0.0066(10) -0.0099(10) -0.0060(9) C6 0.0348(10) 0.0418(12) 0.0369(11) -0.0071(9) -0.0056(9) -0.0034(9) C7 0.0347(11) 0.0433(12) 0.0316(11) -0.0083(9) -0.0038(9) -0.0014(9) C8 0.0311(10) 0.0415(12) 0.0302(10) -0.0055(9) -0.0001(8) -0.0037(8) C9 0.0423(11) 0.0363(11) 0.0378(12) -0.0006(9) -0.0082(9) -0.0028(9) C10 0.0492(12) 0.0412(12) 0.0330(11) -0.0095(9) -0.0076(9) -0.0004(9) C11 0.0472(12) 0.0395(12) 0.0338(11) -0.0042(9) -0.0076(9) 0.0042(9) C12 0.0295(10) 0.0446(12) 0.0293(11) -0.0049(9) -0.0017(8) -0.0041(8) C13 0.0451(12) 0.0412(12) 0.0362(11) -0.0086(9) -0.0069(9) -0.0074(9) C14 0.0351(10) 0.0442(12) 0.0318(11) -0.0095(9) -0.0027(8) -0.0041(9) C15 0.0353(10) 0.0464(13) 0.0321(11) -0.0082(10) -0.0038(8) -0.0078(9) C16 0.0286(10) 0.0462(12) 0.0279(10) -0.0083(9) -0.0005(8) -0.0042(8) C17 0.0421(11) 0.0462(12) 0.0308(11) -0.0051(9) -0.0043(9) -0.0085(9) C18 0.0467(12) 0.0594(15) 0.0341(12) -0.0166(11) -0.0054(9) -0.0111(10) C19 0.0490(12) 0.0463(13) 0.0309(11) -0.0054(9) -0.0044(9) 0.0009(10) C20 0.0452(12) 0.0452(13) 0.0326(11) -0.0093(9) -0.0044(9) -0.0080(9) C21 0.0375(11) 0.0400(11) 0.0250(10) -0.0059(8) -0.0028(8) -0.0048(9) C22 0.0346(10) 0.0380(11) 0.0256(10) -0.0015(8) -0.0075(8) -0.0062(8) C23 0.0317(10) 0.0355(11) 0.0320(11) -0.0021(8) -0.0038(8) -0.0027(8) C24 0.0389(11) 0.0445(12) 0.0276(10) -0.0085(9) -0.0022(8) -0.0026(9) C25 0.0386(11) 0.0491(12) 0.0270(10) -0.0049(9) -0.0084(8) -0.0023(9) C26 0.0370(11) 0.0453(12) 0.0280(11) -0.0038(9) -0.0063(9) 0.0022(9) C27 0.0568(14) 0.0787(17) 0.0403(13) -0.0158(12) -0.0125(11) 0.0250(12) C28 0.0396(11) 0.0416(12) 0.0344(11) -0.0086(9) -0.0079(9) 0.0106(9) C29 0.0401(12) 0.0516(13) 0.0543(14) -0.0107(11) -0.0105(10) -0.0081(10) C30 0.0561(14) 0.0453(13) 0.0431(13) 0.0045(10) -0.0061(11) -0.0013(10) C31 0.0486(13) 0.0678(16) 0.0451(13) -0.0153(12) -0.0195(11) 0.0094(12) C32 0.0434(12) 0.0669(16) 0.0673(16) -0.0291(13) -0.0108(12) -0.0121(11) C33 0.0503(13) 0.0401(12) 0.0516(13) -0.0075(10) 0.0050(11) -0.0054(10) #----------------------------------------------------------------------------# # 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 O1 C23 1.362(2) . ? O2 C21 1.362(2) . ? N1 C1 1.333(3) . ? N1 C5 1.337(3) . ? N2 C19 1.332(3) . ? N2 C18 1.342(3) . ? C1 C2 1.373(3) . ? C2 C3 1.389(3) . ? C3 C4 1.395(3) . ? C3 C6 1.467(3) . ? C4 C5 1.371(3) . ? C6 C7 1.331(3) . ? C7 C8 1.463(3) . ? C8 C10 1.395(3) . ? C8 C9 1.398(3) . ? C9 C13 1.377(3) 2_465 ? C10 C11 1.370(3) 2_465 ? C11 C10 1.370(3) 2_465 ? C11 C12 1.401(3) . ? C12 C13 1.395(3) . ? C12 C14 1.465(3) . ? C13 C9 1.377(3) 2_465 ? C14 C15 1.327(3) . ? C15 C16 1.464(3) . ? C16 C20 1.392(3) . ? C16 C17 1.398(3) . ? C17 C18 1.374(3) . ? C19 C20 1.374(3) . ? C21 C22 1.384(3) . ? C21 C26 1.399(3) . ? C22 C23 1.388(3) . ? C23 C24 1.390(3) . ? C24 C25 1.386(3) . ? C25 C26 1.392(3) . ? C26 C27 1.516(3) . ? C27 C28 1.510(3) . ? C28 C33 1.377(3) . ? C28 C29 1.382(3) . ? C29 C30 1.378(3) . ? C30 C31 1.361(3) . ? C31 C32 1.366(3) . ? C32 C33 1.380(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 115.93(17) . . ? C19 N2 C18 115.97(16) . . ? N1 C1 C2 124.28(19) . . ? C1 C2 C3 119.73(19) . . ? C2 C3 C4 116.19(17) . . ? C2 C3 C6 120.92(17) . . ? C4 C3 C6 122.88(17) . . ? C5 C4 C3 119.90(18) . . ? N1 C5 C4 123.95(19) . . ? C7 C6 C3 124.64(18) . . ? C6 C7 C8 128.10(19) . . ? C10 C8 C9 117.00(17) . . ? C10 C8 C7 118.68(17) . . ? C9 C8 C7 124.32(17) . . ? C13 C9 C8 121.00(18) 2_465 . ? C11 C10 C8 122.08(18) 2_465 . ? C10 C11 C12 121.02(18) 2_465 . ? C13 C12 C11 116.98(17) . . ? C13 C12 C14 120.25(18) . . ? C11 C12 C14 122.76(18) . . ? C9 C13 C12 121.85(18) 2_465 . ? C15 C14 C12 126.05(19) . . ? C14 C15 C16 127.31(19) . . ? C20 C16 C17 116.15(17) . . ? C20 C16 C15 119.56(17) . . ? C17 C16 C15 124.28(18) . . ? C18 C17 C16 119.21(19) . . ? N2 C18 C17 124.51(19) . . ? N2 C19 C20 123.69(19) . . ? C19 C20 C16 120.44(18) . . ? O2 C21 C22 122.01(15) . . ? O2 C21 C26 117.03(16) . . ? C22 C21 C26 120.94(17) . . ? C21 C22 C23 120.65(16) . . ? O1 C23 C22 121.83(15) . . ? O1 C23 C24 118.62(17) . . ? C22 C23 C24 119.55(16) . . ? C25 C24 C23 119.07(17) . . ? C24 C25 C26 122.55(16) . . ? C25 C26 C21 117.21(17) . . ? C25 C26 C27 124.25(16) . . ? C21 C26 C27 118.50(17) . . ? C28 C27 C26 115.27(18) . . ? C33 C28 C29 117.39(18) . . ? C33 C28 C27 121.9(2) . . ? C29 C28 C27 120.72(19) . . ? C30 C29 C28 121.57(19) . . ? C31 C30 C29 120.0(2) . . ? C30 C31 C32 119.62(19) . . ? C31 C32 C33 120.4(2) . . ? C28 C33 C32 121.0(2) . . ? #===END data_3 _database_code_CSD 203761 #----------------------------------------------------------------------------# _audit_creation_date 2003-02-06T09:07:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _chemical_formula_sum 'C40 H32 N4' _chemical_formula_weight 568.7 #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 15.489(2) _cell_length_b 8.0478(10) _cell_length_c 11.5227(14) _cell_angle_alpha 90 _cell_angle_beta 96.991(2) _cell_angle_gamma 90 _cell_volume 1425.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_crystal_description prism _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _exptl_crystal_colour colourless _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# _diffrn_measurement_device_type Nonius _diffrn_measurement_method scanning _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_unetI/netI 0.0614 _diffrn_reflns_number 8705 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 28.33 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.963 _diffrn_measured_fraction_theta_max 0.963 _reflns_number_total 3432 _reflns_number_gt 2551 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# _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^)+(0.0790P)^2^+0.1906P] 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_number_reflns 3432 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0801 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1579 _refine_ls_wR_factor_gt 0.137 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.345 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.072 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 N1 N 0.67119(11) 0.1541(2) 0.40600(13) 0.0257(4) Uani 1 1 d . . . N2 N 0.54822(11) -0.3200(2) 0.64793(15) 0.0312(4) Uani 1 1 d . . . C1 C 0.74382(13) 0.0660(2) 0.42298(15) 0.0250(4) Uani 1 1 d . . . H1 H 0.7643 0.0169 0.3565 0.03 Uiso 1 1 calc R . . C2 C 0.79204(13) 0.0405(2) 0.53096(16) 0.0234(4) Uani 1 1 d . . . H2 H 0.8438 -0.024 0.5374 0.028 Uiso 1 1 calc R . . C3 C 0.76373(12) 0.1101(2) 0.62888(15) 0.0193(4) Uani 1 1 d . . . C4 C 0.68761(12) 0.2019(2) 0.61257(16) 0.0235(4) Uani 1 1 d . . . H4 H 0.6655 0.2522 0.6775 0.028 Uiso 1 1 calc R . . C5 C 0.64409(13) 0.2200(2) 0.50164(16) 0.0248(4) Uani 1 1 d . . . H5 H 0.5918 0.2829 0.4927 0.03 Uiso 1 1 calc R . . C6 C 0.80710(11) 0.0851(2) 0.75139(15) 0.0192(4) Uani 1 1 d . . . H6 H 0.8109 0.194 0.7935 0.023 Uiso 1 1 calc R . . C7 C 0.89550(12) -0.0044(2) 0.77305(15) 0.0196(4) Uani 1 1 d . . . H7 H 0.9107 -0.0574 0.6997 0.023 Uiso 1 1 calc R . . C8 C 0.97283(12) 0.0840(2) 0.83696(14) 0.0191(4) Uani 1 1 d . . . C9 C 0.96522(12) 0.2159(2) 0.91220(15) 0.0207(4) Uani 1 1 d . . . H9 H 0.9154 0.2856 0.9007 0.025 Uiso 1 1 calc R . . C10 C 1.05348(12) 0.0076(2) 0.84341(15) 0.0213(4) Uani 1 1 d . . . H10 H 1.0651 -0.0667 0.7831 0.026 Uiso 1 1 calc R . . C11 C 0.88283(12) -0.0372(2) 1.06432(15) 0.0200(4) Uani 1 1 d . . . H11 H 0.8284 0.0183 1.0612 0.024 Uiso 1 1 calc R . . C12 C 0.89744(12) -0.1469(2) 0.97611(14) 0.0189(4) Uani 1 1 d . . . C13 C 0.97065(12) -0.2473(2) 0.99602(15) 0.0216(4) Uani 1 1 d . . . H13 H 0.9768 -0.339 0.9458 0.026 Uiso 1 1 calc R . . C14 C 0.85258(12) -0.1371(2) 0.85333(15) 0.0200(4) Uani 1 1 d . . . H14 H 0.8502 -0.2494 0.8159 0.024 Uiso 1 1 calc R . . C15 C 0.76413(12) -0.0485(2) 0.82697(15) 0.0195(4) Uani 1 1 d . . . H15 H 0.747 0.0035 0.8996 0.023 Uiso 1 1 calc R . . C16 C 0.68985(12) -0.1466(2) 0.76555(15) 0.0195(4) Uani 1 1 d . . . C17 C 0.70118(13) -0.2645(2) 0.68175(15) 0.0236(4) Uani 1 1 d . . . H17 H 0.7577 -0.2892 0.6625 0.028 Uiso 1 1 calc R . . C18 C 0.62914(13) -0.3463(2) 0.62614(17) 0.0272(4) Uani 1 1 d . . . H18 H 0.6383 -0.4266 0.5685 0.033 Uiso 1 1 calc R . . C19 C 0.53836(14) -0.2037(3) 0.72757(18) 0.0340(5) Uani 1 1 d . . . H19 H 0.481 -0.1796 0.744 0.041 Uiso 1 1 calc R . . C20 C 0.60584(13) -0.1164(3) 0.78748(16) 0.0273(4) Uani 1 1 d . . . H20 H 0.5946 -0.0355 0.8438 0.033 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 N1 0.0255(9) 0.0282(9) 0.0219(8) 0.0038(6) -0.0029(7) -0.0042(7) N2 0.0263(9) 0.0354(10) 0.0299(9) 0.0029(7) -0.0046(7) -0.0084(8) C1 0.0315(11) 0.0253(9) 0.0180(8) -0.0002(7) 0.0019(8) -0.0020(8) C2 0.0241(10) 0.0235(9) 0.0224(9) 0.0024(7) 0.0014(7) 0.0012(8) C3 0.0197(9) 0.0190(8) 0.0185(8) 0.0041(6) -0.0010(7) -0.0054(7) C4 0.0238(10) 0.0253(9) 0.0209(9) 0.0003(7) 0.0015(7) -0.0004(8) C5 0.0199(9) 0.0276(10) 0.0259(9) 0.0048(8) -0.0010(8) 0.0004(8) C6 0.0185(9) 0.0213(9) 0.0172(8) 0.0006(7) -0.0007(7) 0.0003(7) C7 0.0181(9) 0.0242(9) 0.0161(8) 0.0001(7) 0.0007(7) 0.0014(7) C8 0.0187(9) 0.0247(9) 0.0133(8) 0.0056(7) -0.0005(7) -0.0033(7) C9 0.0198(9) 0.0199(9) 0.0219(9) 0.0060(7) 0.0000(7) 0.0002(7) C10 0.0220(9) 0.0290(10) 0.0138(8) 0.0005(7) 0.0056(7) -0.0013(8) C11 0.0149(8) 0.0258(9) 0.0198(8) 0.0042(7) 0.0036(7) 0.0003(7) C12 0.0178(9) 0.0212(9) 0.0171(8) 0.0029(6) -0.0009(7) -0.0059(7) C13 0.0241(10) 0.0181(8) 0.0223(9) 0.0014(7) 0.0008(7) -0.0032(7) C14 0.0187(9) 0.0207(9) 0.0198(8) -0.0008(7) -0.0005(7) -0.0005(7) C15 0.0197(9) 0.0230(9) 0.0156(8) -0.0011(7) 0.0008(7) 0.0013(7) C16 0.0186(9) 0.0230(9) 0.0157(8) 0.0048(7) -0.0022(7) -0.0012(7) C17 0.0196(9) 0.0279(10) 0.0226(9) 0.0008(7) -0.0006(7) 0.0038(8) C18 0.0307(11) 0.0250(10) 0.0240(9) -0.0009(7) -0.0045(8) -0.0010(8) C19 0.0186(10) 0.0507(13) 0.0328(11) -0.0002(10) 0.0032(8) -0.0042(10) C20 0.0221(10) 0.0378(11) 0.0217(9) -0.0034(8) 0.0013(8) 0.0008(9) #----------------------------------------------------------------------------# # 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 N1 C1 1.324(2) . ? N1 C5 1.336(2) . ? N2 C18 1.325(3) . ? N2 C19 1.333(3) . ? C1 C2 1.386(3) . ? C2 C3 1.378(3) . ? C3 C4 1.385(3) . ? C3 C6 1.501(2) . ? C4 C5 1.378(3) . ? C6 C7 1.540(2) . ? C6 C15 1.581(2) . ? C7 C8 1.506(2) . ? C7 C14 1.609(2) . ? C8 C9 1.385(3) . ? C8 C10 1.386(3) . ? C9 C13 1.383(3) 3_757 ? C10 C11 1.380(2) 3_757 ? C11 C10 1.380(2) 3_757 ? C11 C12 1.386(2) . ? C12 C13 1.388(3) . ? C12 C14 1.500(2) . ? C13 C9 1.383(3) 3_757 ? C14 C15 1.542(2) . ? C15 C16 1.500(2) . ? C16 C20 1.377(3) . ? C16 C17 1.380(3) . ? C17 C18 1.384(3) . ? C19 C20 1.374(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 115.94(16) . . ? C18 N2 C19 115.65(17) . . ? N1 C1 C2 124.56(18) . . ? C3 C2 C1 118.95(18) . . ? C2 C3 C4 117.15(16) . . ? C2 C3 C6 124.39(17) . . ? C4 C3 C6 118.37(16) . . ? C5 C4 C3 119.63(18) . . ? N1 C5 C4 123.77(18) . . ? C3 C6 C7 120.15(15) . . ? C3 C6 C15 116.02(14) . . ? C7 C6 C15 91.04(13) . . ? C8 C7 C6 119.80(15) . . ? C8 C7 C14 113.08(13) . . ? C6 C7 C14 88.99(13) . . ? C9 C8 C10 116.83(16) . . ? C9 C8 C7 123.01(17) . . ? C10 C8 C7 118.35(16) . . ? C13 C9 C8 120.72(17) 3_757 . ? C11 C10 C8 121.32(17) 3_757 . ? C10 C11 C12 120.64(17) 3_757 . ? C11 C12 C13 116.92(16) . . ? C11 C12 C14 124.04(16) . . ? C13 C12 C14 117.49(16) . . ? C9 C13 C12 121.07(17) 3_757 . ? C12 C14 C15 120.57(15) . . ? C12 C14 C7 113.62(14) . . ? C15 C14 C7 89.95(13) . . ? C16 C15 C14 117.51(15) . . ? C16 C15 C6 116.64(14) . . ? C14 C15 C6 89.97(13) . . ? C20 C16 C17 116.96(17) . . ? C20 C16 C15 120.54(17) . . ? C17 C16 C15 122.44(17) . . ? C16 C17 C18 119.14(18) . . ? N2 C18 C17 124.37(18) . . ? N2 C19 C20 124.2(2) . . ? C19 C20 C16 119.70(19) . . ?