Electronic Supplementary Material for CrystEngComm This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name N.Champness A.Blake D.J.Ring C.Wilson _publ_contact_author_name 'Neil Champness' _publ_contact_author_email NEIL.CHAMPNESS@NOTTINGHAM.AC.UK data_tzpynh _database_code_depnum_ccdc_archive 'CCDC 288663' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H8 N2, C3 H3 N3 O3' _chemical_formula_sum 'C17 H11 N5 O3' _chemical_formula_weight 333.31 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 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 8.2288(4) _cell_length_b 7.9971(4) _cell_length_c 21.7042(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.5230(10) _cell_angle_gamma 90.00 _cell_volume 1428.22(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4938 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 28.81 _exptl_crystal_description lath _exptl_crystal_colour yellow _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.848 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.67490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS Station 9.8' _diffrn_radiation_monochromator 'silicon (111)' _diffrn_measurement_device_type 'Bruker ApexII CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16193 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.83 _reflns_number_total 4289 _reflns_number_gt 3449 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2003)' _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^)+(0.0768P)^2^+0.1789P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary 'difference fourier map' _atom_sites_solution_hydrogens 'geometrically placed except H3N,H4N,H5N which were found in difference map' _refine_ls_hydrogen_treatment 'refined as riding model except H3N,H4N,H5N which were refined freely' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4289 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1330 _refine_ls_wR_factor_gt 0.1239 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 C1 C 0.42707(13) -0.03959(14) 0.60789(5) 0.0344(2) Uani 1 1 d . . . H1A H 0.3965 -0.1538 0.6110 0.041 Uiso 1 1 calc R . . C2 C 0.52886(12) 0.02710(12) 0.65332(5) 0.0285(2) Uani 1 1 d . . . C3 C 0.58898(14) -0.06685(14) 0.70507(5) 0.0364(2) Uani 1 1 d . . . H3A H 0.5597 -0.1812 0.7092 0.044 Uiso 1 1 calc R . . C4 C 0.68636(14) 0.00441(15) 0.74795(5) 0.0383(3) Uani 1 1 d . . . H4A H 0.7238 -0.0601 0.7820 0.046 Uiso 1 1 calc R . . C5 C 0.73408(12) 0.17638(14) 0.74289(5) 0.0316(2) Uani 1 1 d . . . C6 C 0.83197(13) 0.25803(18) 0.78628(5) 0.0403(3) Uani 1 1 d . . . H6A H 0.8710 0.1959 0.8207 0.048 Uiso 1 1 calc R . . C7 C 0.82087(13) 0.50793(16) 0.73329(5) 0.0384(3) Uani 1 1 d . . . H7A H 0.8516 0.6222 0.7306 0.046 Uiso 1 1 calc R . . C8 C 0.72278(12) 0.44119(13) 0.68620(5) 0.0294(2) Uani 1 1 d . . . C9 C 0.66367(14) 0.53503(13) 0.63417(5) 0.0343(2) Uani 1 1 d . . . H9A H 0.6968 0.6479 0.6290 0.041 Uiso 1 1 calc R . . C10 C 0.56108(14) 0.46420(14) 0.59236(5) 0.0338(2) Uani 1 1 d . . . H10A H 0.5201 0.5297 0.5592 0.041 Uiso 1 1 calc R . . C11 C 0.51341(12) 0.29204(13) 0.59737(4) 0.0268(2) Uani 1 1 d . . . C12 C 0.41147(12) 0.21031(14) 0.55515(5) 0.0328(2) Uani 1 1 d . . . H12A H 0.3694 0.2723 0.5212 0.039 Uiso 1 1 calc R . . C13 C 0.57358(11) 0.19693(12) 0.64751(4) 0.02383(18) Uani 1 1 d . . . C14 C 0.67788(11) 0.27152(12) 0.69195(4) 0.02543(19) Uani 1 1 d . . . C15 C 1.03993(12) 0.24632(15) 0.61041(5) 0.0341(2) Uani 1 1 d . . . C16 C 0.88577(12) 0.00962(14) 0.57149(5) 0.0306(2) Uani 1 1 d . . . C17 C 0.88900(12) 0.27092(13) 0.51374(5) 0.0302(2) Uani 1 1 d . . . N1 N 0.37035(11) 0.04919(13) 0.56021(4) 0.0356(2) Uani 1 1 d . . . N2 N 0.87363(12) 0.41922(15) 0.78190(5) 0.0435(3) Uani 1 1 d . . . N3 N 0.98409(11) 0.08551(13) 0.61446(4) 0.0342(2) Uani 1 1 d . . . H3N H 1.017(2) 0.024(2) 0.6490(8) 0.065(5) Uiso 1 1 d . . . N4 N 0.83839(11) 0.11012(11) 0.52281(4) 0.03002(19) Uani 1 1 d . . . H4N H 0.764(2) 0.062(2) 0.4935(7) 0.061(5) Uiso 1 1 d . . . N5 N 0.99277(12) 0.33270(12) 0.55824(4) 0.0339(2) Uani 1 1 d . . . H5N H 1.035(2) 0.435(2) 0.5535(7) 0.053(4) Uiso 1 1 d . . . O1 O 1.12616(11) 0.30899(13) 0.64972(4) 0.0481(2) Uani 1 1 d . . . O2 O 0.84182(10) -0.13507(11) 0.57557(4) 0.0412(2) Uani 1 1 d . . . O3 O 0.84512(10) 0.35462(10) 0.46937(4) 0.0387(2) 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 0.0336(5) 0.0333(5) 0.0363(5) -0.0066(4) 0.0040(4) -0.0060(4) C2 0.0279(4) 0.0293(5) 0.0283(5) -0.0008(4) 0.0024(4) 0.0004(3) C3 0.0427(6) 0.0304(5) 0.0361(6) 0.0072(4) 0.0053(4) 0.0055(4) C4 0.0415(6) 0.0431(6) 0.0303(5) 0.0106(4) -0.0003(4) 0.0148(5) C5 0.0272(4) 0.0435(6) 0.0241(4) 0.0008(4) -0.0038(3) 0.0095(4) C6 0.0302(5) 0.0638(8) 0.0267(5) -0.0048(5) -0.0082(4) 0.0118(5) C7 0.0302(5) 0.0481(6) 0.0369(6) -0.0134(5) -0.0011(4) -0.0057(4) C8 0.0267(4) 0.0352(5) 0.0265(4) -0.0051(4) 0.0011(3) -0.0024(4) C9 0.0431(6) 0.0288(5) 0.0309(5) 0.0012(4) 0.0029(4) -0.0041(4) C10 0.0437(6) 0.0333(5) 0.0244(4) 0.0058(4) -0.0014(4) 0.0021(4) C11 0.0260(4) 0.0333(5) 0.0211(4) 0.0007(3) -0.0020(3) 0.0012(3) C12 0.0295(5) 0.0450(6) 0.0238(4) -0.0020(4) -0.0048(3) 0.0007(4) C13 0.0219(4) 0.0285(4) 0.0210(4) -0.0005(3) -0.0003(3) 0.0015(3) C14 0.0217(4) 0.0331(5) 0.0215(4) -0.0011(3) -0.0018(3) 0.0025(3) C15 0.0289(5) 0.0486(6) 0.0248(4) -0.0081(4) -0.0060(4) 0.0036(4) C16 0.0242(4) 0.0403(5) 0.0271(5) -0.0015(4) 0.0008(3) 0.0026(4) C17 0.0296(5) 0.0326(5) 0.0283(5) -0.0082(4) -0.0093(4) 0.0042(4) N1 0.0299(4) 0.0460(5) 0.0310(4) -0.0091(4) -0.0024(3) -0.0056(4) N2 0.0286(4) 0.0679(7) 0.0338(5) -0.0158(5) -0.0063(4) 0.0018(4) N3 0.0287(4) 0.0491(5) 0.0247(4) 0.0006(4) -0.0048(3) 0.0027(4) N4 0.0284(4) 0.0344(4) 0.0271(4) -0.0050(3) -0.0069(3) 0.0002(3) N5 0.0361(5) 0.0353(5) 0.0301(4) -0.0077(3) -0.0128(3) 0.0011(4) O1 0.0444(5) 0.0686(6) 0.0311(4) -0.0126(4) -0.0161(3) -0.0034(4) O2 0.0388(4) 0.0430(5) 0.0419(5) 0.0057(3) 0.0025(3) -0.0046(3) O3 0.0444(4) 0.0344(4) 0.0370(4) -0.0025(3) -0.0192(3) 0.0030(3) _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 1.3357(15) . ? C1 C2 1.3939(14) . ? C1 H1A 0.9500 . ? C2 C13 1.4131(14) . ? C2 C3 1.4356(14) . ? C3 C4 1.3488(17) . ? C3 H3A 0.9500 . ? C4 C5 1.4348(17) . ? C4 H4A 0.9500 . ? C5 C6 1.3958(15) . ? C5 C14 1.4163(13) . ? C6 N2 1.3375(18) . ? C6 H6A 0.9500 . ? C7 N2 1.3403(16) . ? C7 C8 1.4021(14) . ? C7 H7A 0.9500 . ? C8 C14 1.4120(14) . ? C8 C9 1.4371(14) . ? C9 C10 1.3575(15) . ? C9 H9A 0.9500 . ? C10 C11 1.4359(15) . ? C10 H10A 0.9500 . ? C11 C12 1.3987(13) . ? C11 C13 1.4135(12) . ? C12 N1 1.3369(15) . ? C12 H12A 0.9500 . ? C13 C14 1.4169(12) . ? C15 O1 1.2131(12) . ? C15 N3 1.3687(16) . ? C15 N5 1.3791(14) . ? C16 O2 1.2158(14) . ? C16 N3 1.3708(13) . ? C16 N4 1.3809(13) . ? C17 O3 1.2245(12) . ? C17 N4 1.3664(14) . ? C17 N5 1.3751(12) . ? N3 H3N 0.935(17) . ? N4 H4N 0.957(17) . ? N5 H5N 0.896(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 N1 C1 C2 123.23(10) . . ? N1 C1 H1A 118.4 . . ? C2 C1 H1A 118.4 . . ? C1 C2 C13 117.38(9) . . ? C1 C2 C3 123.63(10) . . ? C13 C2 C3 118.99(9) . . ? C4 C3 C2 121.14(10) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? C3 C4 C5 120.89(9) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 119.6 . . ? C6 C5 C14 117.24(11) . . ? C6 C5 C4 123.60(10) . . ? C14 C5 C4 119.15(9) . . ? N2 C6 C5 123.35(10) . . ? N2 C6 H6A 118.3 . . ? C5 C6 H6A 118.3 . . ? N2 C7 C8 123.54(11) . . ? N2 C7 H7A 118.2 . . ? C8 C7 H7A 118.2 . . ? C7 C8 C14 116.80(10) . . ? C7 C8 C9 124.23(10) . . ? C14 C8 C9 118.96(9) . . ? C10 C9 C8 120.76(10) . . ? C10 C9 H9A 119.6 . . ? C8 C9 H9A 119.6 . . ? C9 C10 C11 121.20(9) . . ? C9 C10 H10A 119.4 . . ? C11 C10 H10A 119.4 . . ? C12 C11 C13 117.17(9) . . ? C12 C11 C10 124.13(9) . . ? C13 C11 C10 118.70(9) . . ? N1 C12 C11 123.18(9) . . ? N1 C12 H12A 118.4 . . ? C11 C12 H12A 118.4 . . ? C2 C13 C11 119.75(8) . . ? C2 C13 C14 120.03(8) . . ? C11 C13 C14 120.21(9) . . ? C8 C14 C5 120.08(9) . . ? C8 C14 C13 120.12(8) . . ? C5 C14 C13 119.78(9) . . ? O1 C15 N3 122.51(11) . . ? O1 C15 N5 121.94(11) . . ? N3 C15 N5 115.55(9) . . ? O2 C16 N3 123.09(10) . . ? O2 C16 N4 121.84(10) . . ? N3 C16 N4 115.07(10) . . ? O3 C17 N4 122.66(9) . . ? O3 C17 N5 122.19(10) . . ? N4 C17 N5 115.16(9) . . ? C1 N1 C12 119.28(9) . . ? C6 N2 C7 118.98(9) . . ? C15 N3 C16 124.66(9) . . ? C15 N3 H3N 116.7(11) . . ? C16 N3 H3N 118.7(11) . . ? C17 N4 C16 125.00(9) . . ? C17 N4 H4N 118.2(10) . . ? C16 N4 H4N 116.8(10) . . ? C17 N5 C15 124.40(10) . . ? C17 N5 H5N 119.0(10) . . ? C15 N5 H5N 116.6(10) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.344 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.040