Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 ####################################################################### # # 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_funelevm _database_code_depnum_ccdc_archive 'CCDC 293620' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H13 N3 O3' _chemical_formula_weight 235.24 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_H-M ? 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' _cell_length_a 6.9095(5) _cell_length_b 10.2699(7) _cell_length_c 16.4105(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1164.49(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 1.20 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8895 _exptl_absorpt_correction_T_max 0.9726 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 5873 _diffrn_reflns_av_R_equivalents 0.1209 _diffrn_reflns_av_sigmaI/netI 0.0716 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2040 _reflns_number_gt 1993 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0834P)^2^+0.0458P] 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 SHELXL _refine_ls_extinction_coef 0.063(10) _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 -0.9(14) _refine_ls_number_reflns 2040 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1267 _refine_ls_wR_factor_gt 0.1258 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.003 _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 0.1654(2) 0.51536(17) 0.15601(8) 0.0593(5) Uani 1 1 d . . . O2 O 0.14094(19) 0.39981(14) 0.04212(8) 0.0515(4) Uani 1 1 d . . . O3 O 0.6001(3) 0.51624(19) 0.30572(8) 0.0696(5) Uani 1 1 d . . . C10 C 0.7849(3) 0.3344(2) 0.24996(10) 0.0504(5) Uani 1 1 d . . . C9 C 0.5743(3) 0.30807(17) 0.14446(10) 0.0377(4) Uani 1 1 d . . . C11 C 0.8499(4) 0.1548(3) 0.14551(14) 0.0569(5) Uani 1 1 d . . . C1 C -0.1089(2) 0.55203(16) 0.07385(10) 0.0389(4) Uani 1 1 d . . . C2 C -0.1798(3) 0.6434(2) 0.12759(12) 0.0524(5) Uani 1 1 d . . . C3 C -0.3519(4) 0.7071(3) 0.11240(16) 0.0666(6) Uani 1 1 d . . . C4 C -0.4585(3) 0.6771(2) 0.04404(17) 0.0621(6) Uani 1 1 d . . . C5 C -0.3877(3) 0.5870(2) -0.01090(14) 0.0583(5) Uani 1 1 d . . . C6 C -0.2145(3) 0.52486(19) 0.00366(11) 0.0479(5) Uani 1 1 d . . . C7 C 0.0804(3) 0.48412(19) 0.09147(9) 0.0408(4) Uani 1 1 d . . . C8 C 0.6219(3) 0.4316(2) 0.25515(10) 0.0494(5) Uani 1 1 d . . . N2 N 0.7381(2) 0.26337(16) 0.17526(9) 0.0461(4) Uani 1 1 d . . . N1 N 0.4999(2) 0.40622(15) 0.19153(8) 0.0433(4) Uani 1 1 d . . . N3 N 0.4875(2) 0.27070(17) 0.07787(10) 0.0433(4) Uani 1 1 d . . . H1N3 H 0.367(3) 0.322(2) 0.0629(12) 0.041(5) Uiso 1 1 d . . . H2N3 H 0.538(4) 0.220(3) 0.0487(17) 0.059(7) Uiso 1 1 d . . . H1N1 H 0.376(3) 0.456(3) 0.1793(14) 0.057(6) Uiso 1 1 d . . . H2 H -0.111(6) 0.669(5) 0.166(3) 0.130(15) Uiso 1 1 d . . . H3 H -0.403(5) 0.773(4) 0.153(2) 0.096(10) Uiso 1 1 d . . . H4 H -0.576(4) 0.714(2) 0.0375(16) 0.057(6) Uiso 1 1 d . . . H5 H -0.476(5) 0.558(3) -0.0581(19) 0.078(8) Uiso 1 1 d . . . H6 H -0.176(4) 0.469(3) -0.0386(17) 0.066(7) Uiso 1 1 d . . . H10A H 0.771(4) 0.286(3) 0.3001(15) 0.062(7) Uiso 1 1 d . . . H10B H 0.912(3) 0.378(2) 0.2471(12) 0.044(5) Uiso 1 1 d . . . H11A H 0.872(4) 0.103(3) 0.1861(19) 0.080(9) Uiso 1 1 d . . . H11B H 0.971(5) 0.171(3) 0.1382(19) 0.078(9) Uiso 1 1 d . . . H11C H 0.769(6) 0.107(4) 0.105(2) 0.115(13) 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 0.0545(8) 0.0756(10) 0.0479(7) -0.0205(7) -0.0119(6) 0.0168(8) O2 0.0527(7) 0.0522(8) 0.0497(7) -0.0161(6) -0.0066(5) 0.0116(6) O3 0.0933(12) 0.0718(11) 0.0438(7) -0.0183(7) -0.0087(7) 0.0116(10) C10 0.0567(11) 0.0587(12) 0.0356(8) -0.0014(8) -0.0053(8) 0.0002(9) C9 0.0434(8) 0.0351(8) 0.0345(8) 0.0025(6) 0.0049(6) -0.0003(7) C11 0.0619(13) 0.0561(13) 0.0527(11) 0.0011(10) 0.0017(10) 0.0180(11) C1 0.0422(9) 0.0338(9) 0.0408(8) 0.0018(7) 0.0036(6) -0.0019(7) C2 0.0550(11) 0.0535(12) 0.0489(10) -0.0078(9) 0.0034(8) 0.0021(10) C3 0.0665(13) 0.0604(14) 0.0728(14) -0.0031(11) 0.0136(11) 0.0157(12) C4 0.0512(11) 0.0516(12) 0.0833(15) 0.0192(11) 0.0010(10) 0.0093(9) C5 0.0596(11) 0.0467(11) 0.0688(12) 0.0101(10) -0.0189(10) -0.0009(10) C6 0.0578(11) 0.0377(9) 0.0480(9) 0.0006(8) -0.0075(8) 0.0004(9) C7 0.0412(8) 0.0431(9) 0.0380(8) -0.0031(7) 0.0013(7) -0.0015(8) C8 0.0626(11) 0.0528(11) 0.0329(8) -0.0009(7) 0.0017(7) -0.0002(9) N2 0.0530(8) 0.0454(9) 0.0398(7) -0.0022(6) -0.0029(6) 0.0059(7) N1 0.0513(8) 0.0406(8) 0.0379(7) -0.0026(6) 0.0014(6) 0.0041(7) N3 0.0515(9) 0.0385(8) 0.0399(8) -0.0048(7) -0.0018(6) 0.0037(7) _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 C7 1.253(2) . ? O2 C7 1.257(2) . ? O3 C8 1.211(2) . ? C10 N2 1.463(2) . ? C10 C8 1.507(3) . ? C10 H10A 0.96(3) . ? C10 H10B 0.99(2) . ? C9 N3 1.304(2) . ? C9 N2 1.322(3) . ? C9 N1 1.370(2) . ? C11 N2 1.441(3) . ? C11 H11A 0.87(3) . ? C11 H11B 0.86(3) . ? C11 H11C 1.00(4) . ? C1 C2 1.378(3) . ? C1 C6 1.392(2) . ? C1 C7 1.510(3) . ? C2 C3 1.380(3) . ? C2 H2 0.83(5) . ? C3 C4 1.377(4) . ? C3 H3 1.01(4) . ? C4 C5 1.382(4) . ? C4 H4 0.90(3) . ? C5 C6 1.377(3) . ? C5 H5 1.03(3) . ? C6 H6 0.94(3) . ? C8 N1 1.367(2) . ? N1 H1N1 1.02(3) . ? N3 H1N3 1.02(2) . ? N3 H2N3 0.79(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 N2 C10 C8 102.27(15) . . ? N2 C10 H10A 116.0(16) . . ? C8 C10 H10A 102.4(16) . . ? N2 C10 H10B 112.4(12) . . ? C8 C10 H10B 111.7(13) . . ? H10A C10 H10B 111(2) . . ? N3 C9 N2 127.74(17) . . ? N3 C9 N1 121.06(17) . . ? N2 C9 N1 111.19(15) . . ? N2 C11 H11A 107.9(19) . . ? N2 C11 H11B 115(2) . . ? H11A C11 H11B 93(3) . . ? N2 C11 H11C 108(3) . . ? H11A C11 H11C 108(3) . . ? H11B C11 H11C 123(3) . . ? C2 C1 C6 118.67(18) . . ? C2 C1 C7 120.01(16) . . ? C6 C1 C7 121.32(17) . . ? C1 C2 C3 120.9(2) . . ? C1 C2 H2 120(3) . . ? C3 C2 H2 119(3) . . ? C4 C3 C2 120.1(2) . . ? C4 C3 H3 120.1(19) . . ? C2 C3 H3 119.7(19) . . ? C3 C4 C5 119.5(2) . . ? C3 C4 H4 119.0(17) . . ? C5 C4 H4 121.4(17) . . ? C6 C5 C4 120.3(2) . . ? C6 C5 H5 120.7(18) . . ? C4 C5 H5 118.4(18) . . ? C5 C6 C1 120.43(19) . . ? C5 C6 H6 113.7(16) . . ? C1 C6 H6 125.8(16) . . ? O1 C7 O2 124.38(17) . . ? O1 C7 C1 116.72(16) . . ? O2 C7 C1 118.88(15) . . ? O3 C8 N1 125.7(2) . . ? O3 C8 C10 127.35(18) . . ? N1 C8 C10 106.94(15) . . ? C9 N2 C11 126.72(17) . . ? C9 N2 C10 109.66(16) . . ? C11 N2 C10 123.45(17) . . ? C8 N1 C9 109.83(15) . . ? C8 N1 H1N1 124.9(14) . . ? C9 N1 H1N1 125.1(14) . . ? C9 N3 H1N3 115.5(12) . . ? C9 N3 H2N3 119.8(19) . . ? H1N3 N3 H2N3 124(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.1(3) . . . . ? C7 C1 C2 C3 179.65(18) . . . . ? C1 C2 C3 C4 1.9(4) . . . . ? C2 C3 C4 C5 -2.8(4) . . . . ? C3 C4 C5 C6 1.8(3) . . . . ? C4 C5 C6 C1 0.1(3) . . . . ? C2 C1 C6 C5 -0.9(3) . . . . ? C7 C1 C6 C5 179.38(17) . . . . ? C2 C1 C7 O1 0.0(3) . . . . ? C6 C1 C7 O1 179.73(18) . . . . ? C2 C1 C7 O2 179.04(18) . . . . ? C6 C1 C7 O2 -1.3(3) . . . . ? N2 C10 C8 O3 -177.2(2) . . . . ? N2 C10 C8 N1 3.1(2) . . . . ? N3 C9 N2 C11 -5.7(3) . . . . ? N1 C9 N2 C11 175.43(19) . . . . ? N3 C9 N2 C10 178.92(19) . . . . ? N1 C9 N2 C10 0.1(2) . . . . ? C8 C10 N2 C9 -1.9(2) . . . . ? C8 C10 N2 C11 -177.48(19) . . . . ? O3 C8 N1 C9 177.1(2) . . . . ? C10 C8 N1 C9 -3.3(2) . . . . ? N3 C9 N1 C8 -176.84(16) . . . . ? N2 C9 N1 C8 2.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.279 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.054