# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Pradyut Ghosh' _publ_contact_author_email ICPG@IACS.RES.IN _publ_section_title ; Selective visible and near-infrared sensing of fluoride by indole conjugated urea/thiourea ligands ; loop_ _publ_author_name 'Pradyut Ghosh' 'Purnandhu Bose' # Attachment 'Compound-1a.cif' data_compound-1a _database_code_depnum_ccdc_archive 'CCDC 746353' #TrackingRef 'Compound-1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 N6 S' _chemical_formula_weight 360.44 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.3835(16) _cell_length_b 11.4337(12) _cell_length_c 19.997(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3517.3(6) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8184 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 26.45 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.200 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.940 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 CCD AREA DETECTOR' _diffrn_measurement_method 'OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30864 _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3099 _reflns_number_gt 2647 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'MERCURY 2.2' _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^)+(0.0517P)^2^+1.2735P] 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 3099 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.1029 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.54113(11) 0.57815(16) 0.26273(9) 0.0364(4) Uani 1 1 d . . . H1 H 0.5519 0.6237 0.3004 0.044 Uiso 1 1 calc R . . N2 N 0.58896(9) 0.58062(13) 0.20586(7) 0.0397(4) Uani 1 1 d . . . H2 H 0.6335 0.6244 0.1989 0.048 Uiso 1 1 calc R . . C3 C 0.55465(11) 0.50138(15) 0.16087(9) 0.0345(4) Uani 1 1 d . . . C4 C 0.57993(12) 0.47695(17) 0.09549(10) 0.0444(5) Uani 1 1 d . . . H4 H 0.6275 0.5139 0.0760 0.053 Uiso 1 1 calc R . . C5 C 0.53174(14) 0.39628(19) 0.06108(11) 0.0529(5) Uani 1 1 d . . . H5 H 0.5469 0.3783 0.0173 0.064 Uiso 1 1 calc R . . C6 C 0.46003(14) 0.33998(19) 0.09018(10) 0.0508(5) Uani 1 1 d . . . H6 H 0.4291 0.2851 0.0655 0.061 Uiso 1 1 calc R . . C7 C 0.43474(12) 0.36468(16) 0.15486(9) 0.0383(4) Uani 1 1 d . . . H7 H 0.3873 0.3269 0.1739 0.046 Uiso 1 1 calc R . . C8 C 0.48183(10) 0.44754(14) 0.19118(8) 0.0314(4) Uani 1 1 d . . . C9 C 0.47441(10) 0.49876(15) 0.25698(8) 0.0305(4) Uani 1 1 d . . . C10 C 0.41866(10) 0.47135(14) 0.31242(8) 0.0300(4) Uani 1 1 d . . . H10 H 0.4271 0.5123 0.3521 0.036 Uiso 1 1 calc R . . N11 N 0.35763(8) 0.39378(12) 0.31108(6) 0.0297(3) Uani 1 1 d . . . N12 N 0.31889(9) 0.38000(12) 0.37341(6) 0.0319(3) Uani 1 1 d . . . H12 H 0.3319 0.4291 0.4044 0.038 Uiso 1 1 calc R . . C13 C 0.26258(10) 0.29460(14) 0.38764(8) 0.0296(4) Uani 1 1 d . . . S14 S 0.21887(3) 0.20023(4) 0.33242(2) 0.04079(17) Uani 1 1 d . . . N15 N 0.24096(9) 0.28846(12) 0.45343(7) 0.0332(3) Uani 1 1 d . . . H15 H 0.2068 0.2344 0.4677 0.040 Uiso 1 1 calc R . . N16 N 0.27478(8) 0.37071(12) 0.49704(6) 0.0303(3) Uani 1 1 d . . . C17 C 0.24399(10) 0.37159(15) 0.55677(8) 0.0298(4) Uani 1 1 d . . . H17 H 0.2021 0.3171 0.5692 0.036 Uiso 1 1 calc R . . C18 C 0.27404(10) 0.45663(15) 0.60468(7) 0.0287(4) Uani 1 1 d . . . C19 C 0.23848(11) 0.47556(16) 0.66694(8) 0.0352(4) Uani 1 1 d . . . H19 H 0.1938 0.4316 0.6856 0.042 Uiso 1 1 calc R . . N20 N 0.27809(9) 0.56750(14) 0.69711(7) 0.0373(4) Uani 1 1 d . . . H20 H 0.2654 0.5943 0.7361 0.045 Uiso 1 1 calc R . . C21 C 0.34184(11) 0.61145(15) 0.65561(8) 0.0322(4) Uani 1 1 d . . . C22 C 0.40060(12) 0.70196(16) 0.66603(9) 0.0412(5) Uani 1 1 d . . . H22 H 0.4003 0.7454 0.7054 0.049 Uiso 1 1 calc R . . C23 C 0.45953(12) 0.72473(16) 0.61540(10) 0.0444(5) Uani 1 1 d . . . H23 H 0.4994 0.7852 0.6206 0.053 Uiso 1 1 calc R . . C24 C 0.46042(12) 0.65871(16) 0.55662(9) 0.0399(4) Uani 1 1 d . . . H24 H 0.5010 0.6760 0.5236 0.048 Uiso 1 1 calc R . . C25 C 0.40244(10) 0.56849(15) 0.54641(8) 0.0318(4) Uani 1 1 d . . . H25 H 0.4038 0.5251 0.5071 0.038 Uiso 1 1 calc R . . C26 C 0.34133(10) 0.54343(14) 0.59647(7) 0.0272(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0383(9) 0.0377(10) 0.0334(9) 0.0090(7) -0.0078(7) -0.0005(7) N2 0.0329(8) 0.0426(9) 0.0435(9) 0.0155(7) -0.0030(6) -0.0040(6) C3 0.0316(9) 0.0338(9) 0.0381(9) 0.0092(7) 0.0006(7) 0.0065(7) C4 0.0432(10) 0.0427(11) 0.0473(11) 0.0101(9) 0.0141(8) 0.0095(8) C5 0.0603(13) 0.0546(13) 0.0439(11) -0.0048(10) 0.0176(10) 0.0105(10) C6 0.0545(12) 0.0508(12) 0.0470(12) -0.0156(10) 0.0095(9) -0.0001(10) C7 0.0365(9) 0.0368(10) 0.0416(10) -0.0035(8) 0.0061(8) 0.0036(8) C8 0.0294(8) 0.0311(9) 0.0336(9) 0.0056(7) 0.0012(7) 0.0087(7) C9 0.0298(8) 0.0325(9) 0.0292(8) 0.0060(7) -0.0048(7) 0.0049(7) C10 0.0312(8) 0.0336(9) 0.0250(8) 0.0001(7) -0.0050(6) 0.0045(7) N11 0.0303(7) 0.0373(8) 0.0217(7) -0.0004(6) 0.0003(5) 0.0025(6) N12 0.0363(8) 0.0376(8) 0.0219(7) -0.0078(6) 0.0009(6) -0.0047(6) C13 0.0251(8) 0.0357(9) 0.0279(9) -0.0063(7) -0.0007(6) 0.0033(7) S14 0.0349(3) 0.0485(3) 0.0390(3) -0.0197(2) 0.00180(18) -0.00705(19) N15 0.0333(7) 0.0371(8) 0.0293(8) -0.0070(6) 0.0035(6) -0.0100(6) N16 0.0313(7) 0.0348(8) 0.0248(7) -0.0051(6) 0.0013(5) -0.0044(6) C17 0.0271(8) 0.0346(9) 0.0277(8) 0.0003(7) 0.0039(6) -0.0024(7) C18 0.0292(8) 0.0362(9) 0.0207(8) 0.0015(6) 0.0014(6) 0.0018(7) C19 0.0350(9) 0.0467(11) 0.0240(8) 0.0026(7) 0.0037(7) 0.0056(8) N20 0.0432(8) 0.0501(9) 0.0187(7) -0.0048(6) -0.0003(6) 0.0130(7) C21 0.0361(9) 0.0352(9) 0.0251(8) -0.0006(7) -0.0084(7) 0.0107(7) C22 0.0484(11) 0.0348(10) 0.0404(11) -0.0088(8) -0.0212(9) 0.0112(8) C23 0.0417(10) 0.0310(10) 0.0605(13) 0.0009(9) -0.0206(9) -0.0019(8) C24 0.0347(9) 0.0396(10) 0.0454(11) 0.0087(8) -0.0042(8) -0.0041(8) C25 0.0326(9) 0.0355(9) 0.0274(8) 0.0019(7) -0.0008(6) -0.0016(7) C26 0.0303(8) 0.0302(9) 0.0210(8) 0.0003(6) -0.0042(6) 0.0036(6) _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 N2 1.355(2) . ? C1 C9 1.375(2) . ? C1 H1 0.9300 . ? N2 C3 1.382(2) . ? N2 H2 0.8600 . ? C3 C4 1.392(2) . ? C3 C8 1.415(2) . ? C4 C5 1.369(3) . ? C4 H4 0.9300 . ? C5 C6 1.404(3) . ? C5 H5 0.9300 . ? C6 C7 1.380(3) . ? C6 H6 0.9300 . ? C7 C8 1.396(2) . ? C7 H7 0.9300 . ? C8 C9 1.445(2) . ? C9 C10 1.436(2) . ? C10 N11 1.292(2) . ? C10 H10 0.9300 . ? N11 N12 1.3905(18) . ? N12 C13 1.336(2) . ? N12 H12 0.8600 . ? C13 N15 1.359(2) . ? C13 S14 1.6840(16) . ? N15 N16 1.3841(18) . ? N15 H15 0.8600 . ? N16 C17 1.285(2) . ? C17 C18 1.441(2) . ? C17 H17 0.9300 . ? C18 C19 1.377(2) . ? C18 C26 1.443(2) . ? C19 N20 1.357(2) . ? C19 H19 0.9300 . ? N20 C21 1.380(2) . ? N20 H20 0.8600 . ? C21 C22 1.390(3) . ? C21 C26 1.416(2) . ? C22 C23 1.384(3) . ? C22 H22 0.9300 . ? C23 C24 1.397(3) . ? C23 H23 0.9300 . ? C24 C25 1.379(2) . ? C24 H24 0.9300 . ? C25 C26 1.403(2) . ? C25 H25 0.9300 . ? 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 C1 C9 110.42(16) . . ? N2 C1 H1 124.8 . . ? C9 C1 H1 124.8 . . ? C1 N2 C3 109.00(14) . . ? C1 N2 H2 125.5 . . ? C3 N2 H2 125.5 . . ? N2 C3 C4 129.51(17) . . ? N2 C3 C8 108.00(15) . . ? C4 C3 C8 122.42(17) . . ? C5 C4 C3 117.12(18) . . ? C5 C4 H4 121.4 . . ? C3 C4 H4 121.4 . . ? C4 C5 C6 121.76(19) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C7 C6 C5 121.1(2) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 118.69(17) . . ? C6 C7 H7 120.7 . . ? C8 C7 H7 120.7 . . ? C7 C8 C3 118.90(16) . . ? C7 C8 C9 135.05(16) . . ? C3 C8 C9 106.04(15) . . ? C1 C9 C10 121.68(15) . . ? C1 C9 C8 106.55(14) . . ? C10 C9 C8 131.43(15) . . ? N11 C10 C9 124.59(15) . . ? N11 C10 H10 117.7 . . ? C9 C10 H10 117.7 . . ? C10 N11 N12 111.76(13) . . ? C13 N12 N11 123.48(13) . . ? C13 N12 H12 118.3 . . ? N11 N12 H12 118.3 . . ? N12 C13 N15 113.75(14) . . ? N12 C13 S14 125.99(12) . . ? N15 C13 S14 120.26(13) . . ? C13 N15 N16 118.88(13) . . ? C13 N15 H15 120.6 . . ? N16 N15 H15 120.6 . . ? C17 N16 N15 116.90(13) . . ? N16 C17 C18 120.33(15) . . ? N16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 125.43(15) . . ? C19 C18 C26 106.24(14) . . ? C17 C18 C26 128.20(14) . . ? N20 C19 C18 110.21(15) . . ? N20 C19 H19 124.9 . . ? C18 C19 H19 124.9 . . ? C19 N20 C21 109.51(13) . . ? C19 N20 H20 125.2 . . ? C21 N20 H20 125.2 . . ? N20 C21 C22 130.05(16) . . ? N20 C21 C26 107.37(15) . . ? C22 C21 C26 122.54(16) . . ? C23 C22 C21 117.17(16) . . ? C23 C22 H22 121.4 . . ? C21 C22 H22 121.4 . . ? C22 C23 C24 121.35(17) . . ? C22 C23 H23 119.3 . . ? C24 C23 H23 119.3 . . ? C25 C24 C23 121.50(17) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C24 C25 C26 118.73(16) . . ? C24 C25 H25 120.6 . . ? C26 C25 H25 120.6 . . ? C25 C26 C21 118.70(15) . . ? C25 C26 C18 134.61(14) . . ? C21 C26 C18 106.66(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 S14 0.86 2.51 3.3461(15) 164.2 3_655 N20 H20 N11 0.86 2.42 3.1223(19) 139.4 2_565 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.273 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.042 # Attachment 'complex-1b_r.cif' data_complex-1b _database_code_depnum_ccdc_archive 'CCDC 746354' #TrackingRef 'complex-1b_r.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 N6 O1.50' _chemical_formula_weight 353.39 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 32.45(3) _cell_length_b 5.330(5) _cell_length_c 19.800(16) _cell_angle_alpha 90.00 _cell_angle_beta 94.84(4) _cell_angle_gamma 90.00 _cell_volume 3412(5) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 355 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 24.99 _exptl_crystal_description NEEDLE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9817 _exptl_absorpt_correction_T_max 0.9871 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 CCD AREA DETECTOR' _diffrn_measurement_method 'OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15446 _diffrn_reflns_av_R_equivalents 0.1776 _diffrn_reflns_av_sigmaI/netI 0.1638 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3018 _reflns_number_gt 1245 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'MERCURY 1.4' _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 SHELXL _refine_ls_extinction_coef 0.0045(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3018 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1916 _refine_ls_R_factor_gt 0.0701 _refine_ls_wR_factor_ref 0.1673 _refine_ls_wR_factor_gt 0.1290 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.16499(15) 0.9786(9) -0.0957(2) 0.0492(12) Uani 1 1 d . . . C2 C 0.14339(17) 1.1780(9) -0.1282(2) 0.0597(14) Uani 1 1 d . . . H2 H 0.1567 1.2950 -0.1535 0.072 Uiso 1 1 calc R . . C3 C 0.10154(18) 1.1942(10) -0.1213(3) 0.0653(15) Uani 1 1 d . . . H3 H 0.0863 1.3240 -0.1425 0.078 Uiso 1 1 calc R . . C4 C 0.08194(16) 1.0213(10) -0.0834(3) 0.0693(15) Uani 1 1 d . . . H4 H 0.0536 1.0348 -0.0803 0.083 Uiso 1 1 calc R . . C5 C 0.10349(15) 0.8279(9) -0.0498(2) 0.0587(13) Uani 1 1 d . . . H5 H 0.0897 0.7141 -0.0242 0.070 Uiso 1 1 calc R . . C6 C 0.14582(13) 0.8042(8) -0.0547(2) 0.0434(12) Uani 1 1 d . . . C7 C 0.17718(13) 0.6324(8) -0.0275(2) 0.0447(12) Uani 1 1 d . . . C8 C 0.21293(14) 0.7035(9) -0.0544(2) 0.0541(13) Uani 1 1 d . . . H8 H 0.2383 0.6226 -0.0462 0.065 Uiso 1 1 calc R . . N9 N 0.20621(12) 0.9093(8) -0.09476(18) 0.0572(11) Uani 1 1 d . . . H9 H 0.2246 0.9841 -0.1162 0.069 Uiso 1 1 calc R . . C10 C 0.17229(15) 0.4345(8) 0.0206(2) 0.0501(13) Uani 1 1 d . . . H10 H 0.1467 0.3563 0.0212 0.060 Uiso 1 1 calc R . . N11 N 0.20227(11) 0.3623(7) 0.06288(19) 0.0502(10) Uani 1 1 d . . . N12 N 0.19329(11) 0.1615(7) 0.10340(18) 0.0509(10) Uani 1 1 d . . . H12 H 0.1714 0.0735 0.0937 0.061 Uiso 1 1 calc R . . C13 C 0.21920(15) 0.1046(9) 0.1583(2) 0.0460(12) Uani 1 1 d . . . O14 O 0.25153(9) 0.2196(6) 0.17560(14) 0.0532(9) Uani 1 1 d . . . N15 N 0.20767(11) -0.0957(7) 0.19392(18) 0.0555(11) Uani 1 1 d . . . H15 H 0.2240 -0.1551 0.2265 0.067 Uiso 1 1 calc R . . N16 N 0.16935(11) -0.2051(7) 0.17769(18) 0.0487(10) Uani 1 1 d . . . C17 C 0.16221(14) -0.4028(9) 0.2127(2) 0.0479(12) Uani 1 1 d . . . H17 H 0.1833 -0.4658 0.2427 0.057 Uiso 1 1 calc R . . C18 C 0.12280(14) -0.5293(8) 0.2068(2) 0.0470(12) Uani 1 1 d . . . C19 C 0.08561(13) -0.4727(8) 0.1647(2) 0.0449(12) Uani 1 1 d . . . C20 C 0.05579(15) -0.6518(9) 0.1795(3) 0.0531(13) Uani 1 1 d . . . N21 N 0.07363(13) -0.8071(7) 0.2290(2) 0.0669(12) Uani 1 1 d . . . H21 H 0.0615 -0.9305 0.2472 0.080 Uiso 1 1 calc R . . C22 C 0.11359(17) -0.7348(9) 0.2449(2) 0.0604(14) Uani 1 1 d . . . H22 H 0.1320 -0.8130 0.2768 0.072 Uiso 1 1 calc R . . C23 C 0.07345(15) -0.2910(9) 0.1157(2) 0.0570(13) Uani 1 1 d . . . H23 H 0.0920 -0.1675 0.1047 0.068 Uiso 1 1 calc R . . C24 C 0.03413(16) -0.2958(10) 0.0841(3) 0.0679(15) Uani 1 1 d . . . H24 H 0.0262 -0.1739 0.0520 0.081 Uiso 1 1 calc R . . C25 C 0.00592(16) -0.4793(11) 0.0992(3) 0.0709(16) Uani 1 1 d . . . H25 H -0.0204 -0.4804 0.0765 0.085 Uiso 1 1 calc R . . C26 C 0.01643(16) -0.6598(10) 0.1475(3) 0.0642(15) Uani 1 1 d . . . H26 H -0.0024 -0.7824 0.1580 0.077 Uiso 1 1 calc R . . O27 O 0.5000 0.3289(8) 0.2500 0.0765(15) Uani 1 2 d S . . 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 0.050(3) 0.054(3) 0.043(3) -0.006(3) -0.001(2) -0.011(3) C2 0.086(4) 0.050(3) 0.042(3) 0.003(3) 0.001(3) -0.009(3) C3 0.071(4) 0.057(4) 0.065(4) -0.004(3) -0.010(3) 0.003(3) C4 0.062(4) 0.071(4) 0.074(4) 0.000(3) 0.001(3) 0.006(3) C5 0.055(3) 0.059(3) 0.062(3) 0.001(3) 0.007(3) -0.009(3) C6 0.035(3) 0.053(3) 0.042(3) -0.002(2) 0.001(2) -0.009(3) C7 0.041(3) 0.051(3) 0.042(3) 0.000(2) 0.001(2) -0.004(2) C8 0.049(3) 0.070(4) 0.042(3) -0.002(3) -0.007(2) -0.003(3) N9 0.050(3) 0.074(3) 0.049(3) 0.003(2) 0.011(2) -0.012(2) C10 0.050(3) 0.054(3) 0.047(3) -0.006(3) 0.005(2) -0.002(2) N11 0.047(3) 0.059(3) 0.044(2) 0.000(2) 0.001(2) -0.006(2) N12 0.050(3) 0.052(3) 0.049(3) 0.008(2) -0.006(2) -0.012(2) C13 0.045(3) 0.058(4) 0.036(3) 0.003(3) 0.007(2) -0.001(3) O14 0.042(2) 0.069(2) 0.048(2) 0.0021(16) 0.0002(15) -0.0108(17) N15 0.040(3) 0.074(3) 0.051(3) 0.013(2) -0.0086(19) -0.012(2) N16 0.044(2) 0.054(3) 0.048(2) 0.005(2) -0.0001(19) -0.004(2) C17 0.049(3) 0.052(3) 0.043(3) 0.000(3) 0.003(2) 0.007(3) C18 0.047(3) 0.046(3) 0.047(3) -0.001(2) -0.001(2) 0.004(3) C19 0.047(3) 0.041(3) 0.047(3) -0.001(2) 0.009(2) -0.008(2) C20 0.049(3) 0.056(3) 0.056(3) -0.004(3) 0.009(3) -0.003(3) N21 0.070(3) 0.061(3) 0.071(3) 0.010(2) 0.013(2) -0.013(3) C22 0.066(4) 0.060(4) 0.055(3) 0.009(3) 0.001(3) 0.005(3) C23 0.053(3) 0.060(3) 0.059(3) 0.003(3) 0.011(3) -0.008(3) C24 0.057(4) 0.076(4) 0.068(4) -0.003(3) -0.004(3) 0.005(3) C25 0.053(4) 0.086(4) 0.072(4) -0.013(4) -0.002(3) -0.004(3) C26 0.056(4) 0.062(4) 0.076(4) -0.002(3) 0.011(3) -0.014(3) O27 0.084(4) 0.056(3) 0.094(4) 0.000 0.028(3) 0.000 _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 N9 1.386(5) . ? C1 C2 1.400(6) . ? C1 C6 1.412(6) . ? C2 C3 1.379(6) . ? C2 H2 0.9300 . ? C3 C4 1.378(6) . ? C3 H3 0.9300 . ? C4 C5 1.383(6) . ? C4 H4 0.9300 . ? C5 C6 1.391(6) . ? C5 H5 0.9300 . ? C6 C7 1.439(6) . ? C7 C8 1.370(6) . ? C7 C10 1.440(6) . ? C8 N9 1.364(5) . ? C8 H8 0.9300 . ? N9 H9 0.8600 . ? C10 N11 1.287(5) . ? C10 H10 0.9300 . ? N11 N12 1.383(5) . ? N12 C13 1.352(5) . ? N12 H12 0.8600 . ? C13 O14 1.238(5) . ? C13 N15 1.349(5) . ? N15 N16 1.387(4) . ? N15 H15 0.8600 . ? N16 C17 1.292(5) . ? C17 C18 1.441(6) . ? C17 H17 0.9300 . ? C18 C22 1.376(6) . ? C18 C19 1.440(6) . ? C19 C23 1.403(6) . ? C19 C20 1.408(6) . ? C20 N21 1.373(5) . ? C20 C26 1.378(6) . ? N21 C22 1.364(5) . ? N21 H21 0.8600 . ? C22 H22 0.9300 . ? C23 C24 1.373(6) . ? C23 H23 0.9300 . ? C24 C25 1.389(6) . ? C24 H24 0.9300 . ? C25 C26 1.378(6) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? 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 N9 C1 C2 130.8(5) . . ? N9 C1 C6 106.8(4) . . ? C2 C1 C6 122.4(5) . . ? C3 C2 C1 117.5(5) . . ? C3 C2 H2 121.3 . . ? C1 C2 H2 121.3 . . ? C4 C3 C2 121.0(5) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 121.5(5) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C4 C5 C6 119.8(5) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 117.7(4) . . ? C5 C6 C7 134.7(4) . . ? C1 C6 C7 107.6(4) . . ? C8 C7 C6 105.9(4) . . ? C8 C7 C10 127.1(4) . . ? C6 C7 C10 126.9(4) . . ? N9 C8 C7 110.5(4) . . ? N9 C8 H8 124.7 . . ? C7 C8 H8 124.7 . . ? C8 N9 C1 109.2(4) . . ? C8 N9 H9 125.4 . . ? C1 N9 H9 125.4 . . ? N11 C10 C7 122.0(4) . . ? N11 C10 H10 119.0 . . ? C7 C10 H10 119.0 . . ? C10 N11 N12 115.1(4) . . ? C13 N12 N11 119.6(4) . . ? C13 N12 H12 120.2 . . ? N11 N12 H12 120.2 . . ? O14 C13 N15 120.9(4) . . ? O14 C13 N12 124.5(4) . . ? N15 C13 N12 114.6(4) . . ? C13 N15 N16 119.7(4) . . ? C13 N15 H15 120.2 . . ? N16 N15 H15 120.2 . . ? C17 N16 N15 114.6(4) . . ? N16 C17 C18 122.4(4) . . ? N16 C17 H17 118.8 . . ? C18 C17 H17 118.8 . . ? C22 C18 C19 105.9(4) . . ? C22 C18 C17 124.1(4) . . ? C19 C18 C17 130.0(4) . . ? C23 C19 C20 117.0(4) . . ? C23 C19 C18 135.9(4) . . ? C20 C19 C18 107.1(4) . . ? N21 C20 C26 129.0(5) . . ? N21 C20 C19 107.6(4) . . ? C26 C20 C19 123.5(5) . . ? C22 N21 C20 109.2(4) . . ? C22 N21 H21 125.4 . . ? C20 N21 H21 125.4 . . ? N21 C22 C18 110.2(4) . . ? N21 C22 H22 124.9 . . ? C18 C22 H22 124.9 . . ? C24 C23 C19 119.9(5) . . ? C24 C23 H23 120.1 . . ? C19 C23 H23 120.1 . . ? C23 C24 C25 121.2(5) . . ? C23 C24 H24 119.4 . . ? C25 C24 H24 119.4 . . ? C26 C25 C24 120.8(5) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C20 C26 C25 117.6(5) . . ? C20 C26 H26 121.2 . . ? C25 C26 H26 121.2 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N9 H9 O14 0.86 2.15 2.954(5) 155.2 7_565 N9 H9 N11 0.86 2.64 3.223(6) 125.7 7_565 N15 H15 O14 0.86 2.14 2.970(5) 162.4 4_545 N21 H21 O27 0.86 2.38 3.132(5) 146.8 3_435 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.267 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.062