# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Cotton, Graham' 'Maltman, Beatrice' _publ_contact_author_name 'Cotton, Graham' _publ_contact_author_email graham.cotton@almacgroup.com _publ_section_title ; 9-Aminoacridine peptide derivatives as versatile reporter systems for use in fluorescence lifetime assays ; # Attachment 'Cotton-compound2.cif' data_sp8037 _database_code_depnum_ccdc_archive 'CCDC 789850' #TrackingRef 'Cotton-compound2.cif' _audit_creation_method SHELXL-97 _audit_creation_date 08-07-23 _chemical_compound_source 'Beatrice Maltman, Almac Sciences ' _exptl_crystal_recrystallization_method ; >From MeOH/EtOH at 4degC ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '[C16 H15 N2 O2]Cl.MeOH' _chemical_formula_sum 'C17 H19 Cl N2 O3' _chemical_formula_weight 334.79 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6896(6) _cell_length_b 9.7414(6) _cell_length_c 10.8210(7) _cell_angle_alpha 75.196(4) _cell_angle_beta 72.166(4) _cell_angle_gamma 70.339(4) _cell_volume 809.17(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4945 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _exptl_crystal_description block _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.253 _exptl_absorpt_correction_type Multiscan _exptl_absorpt_correction_T_min 0.7523 _exptl_absorpt_correction_T_max 0.9280 _exptl_absorpt_process_details SADABS _exptl_special_details ; The crystal was cut out of a larger conglomerate. Data collection strategy optimised with COSMO. Oxford Crysosystems LT device. ; _diffrn_ambient_temperature 150(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 'Bruker SMART APEX CCD' _diffrn_measurement_method 'Omega and phi' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13860 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.02 _reflns_number_total 3521 _reflns_number_gt 2845 _reflns_threshold_expression >2sigma(I) _computing_data_collection Smart _computing_cell_refinement Saint _computing_data_reduction Saint _computing_structure_solution SHELXTL-XS _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, Mercury' _computing_publication_material 'XCIF, PLATON' _refine_special_details ; Diffraction data were merged with SORTAV. H-atoms were clearly visible in difference maps, but they are placed in idealised positions and allowed to ride on their parent atoms. OH and Me groups were treated as rotating rigid groups. CHECKCIF Output: 761_ALERT_1_A CIF Contains no X-H Bonds ...................... ? 762_ALERT_1_A CIF Contains no X-Y-H or H-Y-H Angles .......... ? H-atoms bond distances and angles are all idealised. 042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? The one given is more chemically meaningful 061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82 Sadabs corrects for all systematic errors that lead to disparities in the intensities of symmetry-equivalent data. These may include absorption by the mount, crystal decay, changes in the volume of the crystal illuminated, etc. 911_ALERT_3_C # Missing FCF Refl Between THmin & STh/L= 0.600 4 912_ALERT_3_C # Missing FCF Reflections Above STh/L= 0.600 18 No problem here: #=============================================================================== Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 20.82 0.500 0.999 1703 1701 2 23.01 0.550 0.999 2262 2260 2 25.24 0.600 0.999 2924 2920 4 #----------------------------------------------------------- ACTA Min. Res. ---- 27.02 0.639 0.994 3543 3521 22 ; _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^)+(0.0606P)^2^+0.5751P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'Riding/rotating rigid group (Me and OH)' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3521 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1409 _refine_ls_wR_factor_gt 0.1348 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.2720(2) 0.6224(2) 0.24190(18) 0.0262(4) Uani 1 1 d . . . H1 H 0.2453 0.7161 0.2489 0.031 Uiso 1 1 calc R . . C2 C 0.1483(3) 0.5518(2) 0.2862(2) 0.0227(4) Uani 1 1 d . . . C3 C -0.0168(3) 0.6292(2) 0.3431(2) 0.0253(5) Uani 1 1 d . . . H3 H -0.0419 0.7296 0.3516 0.030 Uiso 1 1 calc R . . C4 C -0.1412(3) 0.5596(2) 0.3862(2) 0.0242(5) Uani 1 1 d . . . H4 H -0.2527 0.6131 0.4235 0.029 Uiso 1 1 calc R . . C5 C -0.1075(3) 0.4091(2) 0.3764(2) 0.0230(4) Uani 1 1 d . . . C6 C 0.0540(3) 0.3340(2) 0.3221(2) 0.0237(4) Uani 1 1 d . . . H6 H 0.0781 0.2331 0.3158 0.028 Uiso 1 1 calc R . . C7 C 0.1865(3) 0.4026(2) 0.2750(2) 0.0223(4) Uani 1 1 d . . . C8 C 0.3552(3) 0.3259(2) 0.2153(2) 0.0240(4) Uani 1 1 d . . . C9 C 0.4821(3) 0.4043(2) 0.1723(2) 0.0255(5) Uani 1 1 d . . . C10 C 0.6526(3) 0.3381(3) 0.1153(2) 0.0324(5) Uani 1 1 d . . . H10 H 0.6874 0.2376 0.1044 0.039 Uiso 1 1 calc R . . C11 C 0.7683(3) 0.4168(3) 0.0755(3) 0.0385(6) Uani 1 1 d . . . H11 H 0.8828 0.3709 0.0375 0.046 Uiso 1 1 calc R . . C12 C 0.7181(3) 0.5652(3) 0.0908(2) 0.0387(6) Uani 1 1 d . . . H12 H 0.7993 0.6191 0.0623 0.046 Uiso 1 1 calc R . . C13 C 0.5548(3) 0.6339(3) 0.1458(2) 0.0330(5) Uani 1 1 d . . . H13 H 0.5226 0.7346 0.1559 0.040 Uiso 1 1 calc R . . C14 C 0.4343(3) 0.5537(2) 0.1876(2) 0.0263(5) Uani 1 1 d . . . C51 C -0.2508(3) 0.3386(2) 0.4262(2) 0.0250(5) Uani 1 1 d . . . H51A H -0.3325 0.3872 0.3705 0.030 Uiso 1 1 calc R . . H51B H -0.3096 0.3564 0.5172 0.030 Uiso 1 1 calc R . . C52 C -0.1945(3) 0.1733(2) 0.4257(2) 0.0295(5) Uani 1 1 d . . . H52A H -0.1279 0.1554 0.3361 0.035 Uiso 1 1 calc R . . H52B H -0.1192 0.1243 0.4864 0.035 Uiso 1 1 calc R . . C53 C -0.3343(3) 0.1031(2) 0.4649(2) 0.0282(5) Uani 1 1 d . . . O54 O -0.4829(2) 0.17026(18) 0.48627(19) 0.0380(4) Uani 1 1 d . . . O55 O -0.2781(2) -0.04206(18) 0.4710(2) 0.0397(4) Uani 1 1 d . . . H55 H -0.3597 -0.0769 0.4871 0.060 Uiso 1 1 calc R . . N81 N 0.3941(2) 0.1875(2) 0.19870(18) 0.0288(4) Uani 1 1 d . . . H811 H 0.3158 0.1408 0.2245 0.035 Uiso 1 1 calc R . . H812 H 0.4983 0.1419 0.1619 0.035 Uiso 1 1 calc R . . Cl1 Cl 0.17968(9) 0.96243(6) 0.23170(6) 0.0401(2) Uani 1 1 d . . . O60 O 0.3175(3) 1.0037(2) -0.06614(19) 0.0575(6) Uani 1 1 d . . . H60 H 0.2816 0.9898 0.0162 0.086 Uiso 1 1 calc R . . C60 C 0.1870(5) 1.0864(4) -0.1233(4) 0.0674(10) Uani 1 1 d . . . H601 H 0.1042 1.1531 -0.0645 0.101 Uiso 1 1 calc R . . H602 H 0.1332 1.0206 -0.1387 0.101 Uiso 1 1 calc R . . H603 H 0.2301 1.1445 -0.2074 0.101 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 0.0315(10) 0.0194(9) 0.0302(10) -0.0052(7) -0.0083(8) -0.0088(8) C2 0.0273(11) 0.0212(10) 0.0228(10) -0.0034(8) -0.0093(8) -0.0080(8) C3 0.0309(12) 0.0170(10) 0.0280(11) -0.0055(8) -0.0098(9) -0.0034(8) C4 0.0239(11) 0.0212(10) 0.0257(11) -0.0067(8) -0.0073(9) -0.0009(8) C5 0.0270(11) 0.0216(10) 0.0224(10) -0.0045(8) -0.0084(8) -0.0067(9) C6 0.0286(12) 0.0194(10) 0.0247(10) -0.0048(8) -0.0067(9) -0.0080(8) C7 0.0262(11) 0.0200(10) 0.0228(10) -0.0055(8) -0.0073(8) -0.0064(8) C8 0.0275(12) 0.0227(10) 0.0226(10) -0.0046(8) -0.0080(9) -0.0057(9) C9 0.0273(12) 0.0277(11) 0.0232(10) -0.0038(8) -0.0077(9) -0.0090(9) C10 0.0290(12) 0.0360(13) 0.0314(12) -0.0070(10) -0.0070(10) -0.0077(10) C11 0.0261(13) 0.0511(16) 0.0371(13) -0.0099(11) -0.0037(10) -0.0109(11) C12 0.0343(14) 0.0528(16) 0.0373(13) -0.0039(11) -0.0091(11) -0.0251(12) C13 0.0376(14) 0.0345(13) 0.0332(12) -0.0035(10) -0.0111(10) -0.0176(11) C14 0.0290(12) 0.0292(11) 0.0249(10) -0.0029(9) -0.0096(9) -0.0118(9) C51 0.0230(11) 0.0246(11) 0.0273(11) -0.0056(8) -0.0045(9) -0.0071(9) C52 0.0266(12) 0.0243(11) 0.0370(12) -0.0046(9) -0.0058(10) -0.0085(9) C53 0.0310(13) 0.0240(11) 0.0300(11) -0.0035(9) -0.0072(9) -0.0095(9) O54 0.0279(9) 0.0264(9) 0.0597(11) -0.0102(8) -0.0056(8) -0.0098(7) O55 0.0291(9) 0.0242(8) 0.0635(12) -0.0091(8) -0.0035(8) -0.0102(7) N81 0.0243(10) 0.0237(9) 0.0355(10) -0.0115(8) 0.0003(8) -0.0049(7) Cl1 0.0511(4) 0.0269(3) 0.0430(3) -0.0157(2) 0.0028(3) -0.0174(3) O60 0.0502(13) 0.0628(14) 0.0400(11) -0.0186(10) -0.0122(9) 0.0172(10) C60 0.075(2) 0.0491(19) 0.075(2) -0.0159(17) -0.041(2) 0.0118(17) _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 C14 1.356(3) . ? N1 C2 1.368(3) . ? C2 C3 1.405(3) . ? C2 C7 1.407(3) . ? C3 C4 1.367(3) . ? C4 C5 1.420(3) . ? C5 C6 1.369(3) . ? C5 C51 1.512(3) . ? C6 C7 1.419(3) . ? C7 C8 1.433(3) . ? C8 N81 1.321(3) . ? C8 C9 1.445(3) . ? C9 C14 1.411(3) . ? C9 C10 1.412(3) . ? C10 C11 1.367(3) . ? C11 C12 1.400(4) . ? C12 C13 1.365(4) . ? C13 C14 1.411(3) . ? C51 C52 1.519(3) . ? C52 C53 1.490(3) . ? C53 O54 1.214(3) . ? C53 O55 1.322(3) . ? O60 C60 1.371(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 C14 N1 C2 122.56(18) . . ? N1 C2 C3 119.56(19) . . ? N1 C2 C7 120.15(19) . . ? C3 C2 C7 120.29(19) . . ? C4 C3 C2 119.77(19) . . ? C3 C4 C5 121.53(19) . . ? C6 C5 C4 118.34(19) . . ? C6 C5 C51 122.80(18) . . ? C4 C5 C51 118.87(19) . . ? C5 C6 C7 121.93(19) . . ? C2 C7 C6 118.13(19) . . ? C2 C7 C8 119.47(19) . . ? C6 C7 C8 122.38(19) . . ? N81 C8 C7 121.1(2) . . ? N81 C8 C9 120.6(2) . . ? C7 C8 C9 118.33(19) . . ? C14 C9 C10 118.3(2) . . ? C14 C9 C8 118.8(2) . . ? C10 C9 C8 122.9(2) . . ? C11 C10 C9 120.8(2) . . ? C10 C11 C12 120.0(2) . . ? C13 C12 C11 121.3(2) . . ? C12 C13 C14 119.2(2) . . ? N1 C14 C9 120.6(2) . . ? N1 C14 C13 119.1(2) . . ? C9 C14 C13 120.3(2) . . ? C5 C51 C52 113.54(18) . . ? C53 C52 C51 114.63(19) . . ? O54 C53 O55 123.3(2) . . ? O54 C53 C52 124.5(2) . . ? O55 C53 C52 112.1(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.02 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.368 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.082