# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Grossel, Martin' 'Bailey, Andrew' 'Horton, Peter' _publ_contact_author_name 'Grossel, Martin' _publ_contact_author_email mcg1@soton.ac.uk _publ_section_title ; Self-assembly into infinite tapes by 2,7-disubstituted-1,8-naphthyridines in the solid state ; # Attachment '- combined.cif' data_3a _database_code_depnum_ccdc_archive 'CCDC 779572' #TrackingRef '- combined.cif' loop_ _chemical_name_systematic ; Dimethyl 1,8-naphthyridine-2,7-dicarboxylate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2 O4' _chemical_formula_sum 'C12 H10 N2 O4' _chemical_formula_weight 246.22 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc 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' _cell_length_a 3.7854(3) _cell_length_b 46.326(5) _cell_length_c 6.1728(6) _cell_angle_alpha 90.00 _cell_angle_beta 104.357(6) _cell_angle_gamma 90.00 _cell_volume 1048.68(17) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 11918 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour 'Clear Colourless' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7552 _exptl_absorpt_correction_T_max 0.9692 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5214 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -60 _diffrn_reflns_limit_k_max 54 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1196 _reflns_number_gt 1049 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0941P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1196 _refine_ls_number_parameters 165 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1237 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.055 _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 C2 C 0.4074(8) 0.07952(6) 0.1436(5) 0.0202(7) Uani 1 1 d . . . C2A C -0.0443(8) 0.17071(7) 0.1778(5) 0.0200(6) Uani 1 1 d . . . C3 C 0.5799(8) 0.07875(7) 0.3756(5) 0.0239(7) Uani 1 1 d . . . H3 H 0.7215 0.0625 0.4392 0.029 Uiso 1 1 calc R . . C3A C 0.0728(8) 0.17203(7) 0.4131(5) 0.0226(7) Uani 1 1 d . . . H3A H 0.0170 0.1884 0.4913 0.027 Uiso 1 1 calc R . . C4 C 0.5390(9) 0.10177(7) 0.5061(5) 0.0253(7) Uani 1 1 d . . . H4 H 0.6465 0.1016 0.6625 0.030 Uiso 1 1 calc R . . C4A C 0.2661(9) 0.14969(7) 0.5268(5) 0.0239(7) Uani 1 1 d . . . H4A H 0.3525 0.1503 0.6849 0.029 Uiso 1 1 calc R . . C5 C 0.3350(9) 0.12561(6) 0.4043(5) 0.0215(6) Uani 1 1 d . . . C6 C 0.1864(8) 0.12517(6) 0.1680(5) 0.0185(6) Uani 1 1 d . . . C7 C 0.4551(8) 0.05286(7) 0.0145(5) 0.0231(7) Uani 1 1 d . . . C7A C -0.2299(8) 0.19708(6) 0.0638(5) 0.0208(7) Uani 1 1 d . . . C10 C 0.2832(10) 0.02584(7) -0.3136(6) 0.0277(7) Uani 1 1 d . . . H10A H 0.5422 0.0220 -0.3003 0.042 Uiso 1 1 calc R . . H10B H 0.1573 0.0281 -0.4717 0.042 Uiso 1 1 calc R . . H10C H 0.1753 0.0097 -0.2501 0.042 Uiso 1 1 calc R . . C10A C -0.3958(9) 0.22524(7) -0.2625(5) 0.0255(7) Uani 1 1 d . . . H10D H -0.6439 0.2273 -0.2432 0.038 Uiso 1 1 calc R . . H10E H -0.4043 0.2242 -0.4222 0.038 Uiso 1 1 calc R . . H10F H -0.2494 0.2419 -0.1963 0.038 Uiso 1 1 calc R . . N1 N 0.2196(7) 0.10162(5) 0.0399(4) 0.0209(6) Uani 1 1 d . . . N1A N 0.0052(8) 0.14840(5) 0.0553(4) 0.0203(5) Uani 1 1 d . . . O8 O 0.6633(7) 0.03383(5) 0.0974(4) 0.0317(6) Uani 1 1 d . . . O8A O -0.3635(7) 0.21540(5) 0.1603(4) 0.0295(6) Uani 1 1 d . . . O9 O 0.2460(6) 0.05215(4) -0.1932(3) 0.0234(5) Uani 1 1 d . . . O9A O -0.2320(6) 0.19899(4) -0.1519(4) 0.0227(5) 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 C2 0.0184(15) 0.0184(15) 0.0229(15) 0.0048(11) 0.0031(12) -0.0032(12) C2A 0.0177(15) 0.0201(15) 0.0228(14) -0.0023(11) 0.0060(11) -0.0046(12) C3 0.0170(16) 0.0248(16) 0.0262(15) 0.0076(13) -0.0013(12) 0.0000(12) C3A 0.0241(17) 0.0222(15) 0.0228(15) -0.0054(12) 0.0081(12) -0.0049(13) C4 0.0209(17) 0.0309(18) 0.0217(14) 0.0053(12) 0.0009(12) -0.0060(13) C4A 0.0247(17) 0.0271(16) 0.0178(13) -0.0015(12) 0.0011(11) -0.0059(13) C5 0.0231(15) 0.0221(15) 0.0182(14) 0.0013(11) 0.0031(11) -0.0057(12) C6 0.0154(15) 0.0197(14) 0.0209(14) 0.0018(11) 0.0055(11) -0.0042(12) C7 0.0207(17) 0.0201(15) 0.0277(16) 0.0039(12) 0.0044(12) -0.0032(12) C7A 0.0209(17) 0.0168(14) 0.0251(15) -0.0022(11) 0.0064(12) -0.0039(12) C10 0.0298(18) 0.0204(15) 0.0326(16) -0.0027(12) 0.0070(13) 0.0039(13) C10A 0.0274(18) 0.0187(14) 0.0297(16) 0.0036(12) 0.0059(13) 0.0045(13) N1 0.0209(14) 0.0197(13) 0.0216(12) 0.0006(10) 0.0044(9) -0.0009(11) N1A 0.0179(13) 0.0200(12) 0.0227(12) 0.0002(10) 0.0044(9) -0.0016(11) O8 0.0319(14) 0.0239(11) 0.0356(13) 0.0026(10) 0.0014(10) 0.0067(10) O8A 0.0360(14) 0.0219(12) 0.0334(12) -0.0043(10) 0.0138(10) 0.0036(10) O9 0.0270(12) 0.0158(10) 0.0261(12) -0.0004(8) 0.0042(9) 0.0046(9) O9A 0.0262(12) 0.0184(10) 0.0230(10) 0.0004(8) 0.0053(8) 0.0038(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 N1 1.318(4) . ? C2 C3 1.419(4) . ? C2 C7 1.505(4) . ? C2A N1A 1.321(4) . ? C2A C3A 1.411(4) . ? C2A C7A 1.495(4) . ? C3 C4 1.368(4) . ? C3 H3 0.9500 . ? C3A C4A 1.358(4) . ? C3A H3A 0.9500 . ? C4 C5 1.404(4) . ? C4 H4 0.9500 . ? C4A C5 1.407(4) . ? C4A H4A 0.9500 . ? C5 C6 1.427(4) . ? C6 N1A 1.370(4) . ? C6 N1 1.371(4) . ? C7 O8 1.208(4) . ? C7 O9 1.330(3) . ? C7A O8A 1.216(4) . ? C7A O9A 1.333(4) . ? C10 O9 1.452(4) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10A O9A 1.456(4) . ? C10A H10D 0.9800 . ? C10A H10E 0.9800 . ? C10A H10F 0.9800 . ? 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 C2 C3 124.6(3) . . ? N1 C2 C7 120.1(3) . . ? C3 C2 C7 115.3(3) . . ? N1A C2A C3A 124.7(3) . . ? N1A C2A C7A 119.1(2) . . ? C3A C2A C7A 116.1(3) . . ? C4 C3 C2 118.9(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C4A C3A C2A 119.4(3) . . ? C4A C3A H3A 120.3 . . ? C2A C3A H3A 120.3 . . ? C3 C4 C5 118.7(3) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C3A C4A C5 118.3(3) . . ? C3A C4A H4A 120.8 . . ? C5 C4A H4A 120.8 . . ? C4 C5 C4A 122.5(3) . . ? C4 C5 C6 118.7(3) . . ? C4A C5 C6 118.8(3) . . ? N1A C6 N1 116.0(3) . . ? N1A C6 C5 121.9(3) . . ? N1 C6 C5 122.1(3) . . ? O8 C7 O9 124.1(3) . . ? O8 C7 C2 121.7(3) . . ? O9 C7 C2 114.2(2) . . ? O8A C7A O9A 122.9(3) . . ? O8A C7A C2A 122.9(3) . . ? O9A C7A C2A 114.2(2) . . ? O9 C10 H10A 109.5 . . ? O9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O9A C10A H10D 109.5 . . ? O9A C10A H10E 109.5 . . ? H10D C10A H10E 109.5 . . ? O9A C10A H10F 109.5 . . ? H10D C10A H10F 109.5 . . ? H10E C10A H10F 109.5 . . ? C2 N1 C6 117.0(3) . . ? C2A N1A C6 116.6(3) . . ? C7 O9 C10 113.9(2) . . ? C7A O9A C10A 114.8(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 N1 C2 C3 C4 3.1(5) . . . . ? C7 C2 C3 C4 -177.8(3) . . . . ? N1A C2A C3A C4A 3.3(5) . . . . ? C7A C2A C3A C4A -175.4(3) . . . . ? C2 C3 C4 C5 -1.6(4) . . . . ? C2A C3A C4A C5 -1.4(4) . . . . ? C3 C4 C5 C4A 177.3(3) . . . . ? C3 C4 C5 C6 -1.6(4) . . . . ? C3A C4A C5 C4 178.5(3) . . . . ? C3A C4A C5 C6 -2.6(5) . . . . ? C4 C5 C6 N1A -175.6(3) . . . . ? C4A C5 C6 N1A 5.5(4) . . . . ? C4 C5 C6 N1 3.7(4) . . . . ? C4A C5 C6 N1 -175.2(3) . . . . ? N1 C2 C7 O8 170.2(3) . . . . ? C3 C2 C7 O8 -9.0(4) . . . . ? N1 C2 C7 O9 -10.9(4) . . . . ? C3 C2 C7 O9 169.9(3) . . . . ? N1A C2A C7A O8A 161.8(3) . . . . ? C3A C2A C7A O8A -19.5(4) . . . . ? N1A C2A C7A O9A -19.1(4) . . . . ? C3A C2A C7A O9A 159.6(3) . . . . ? C3 C2 N1 C6 -1.0(4) . . . . ? C7 C2 N1 C6 179.9(3) . . . . ? N1A C6 N1 C2 177.0(3) . . . . ? C5 C6 N1 C2 -2.4(4) . . . . ? C3A C2A N1A C6 -0.5(5) . . . . ? C7A C2A N1A C6 178.1(2) . . . . ? N1 C6 N1A C2A 176.8(3) . . . . ? C5 C6 N1A C2A -3.8(4) . . . . ? O8 C7 O9 C10 1.2(4) . . . . ? C2 C7 O9 C10 -177.7(3) . . . . ? O8A C7A O9A C10A 2.0(4) . . . . ? C2A C7A O9A C10A -177.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.400 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.105 data_3b _database_code_depnum_ccdc_archive 'CCDC 779573' #TrackingRef '- combined.cif' _chemical_name_systematic ; Diethyl 1,8-naphthyridine-2,7-dicarboxylate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 N2 O4' _chemical_formula_sum 'C14 H14 N2 O4' _chemical_formula_weight 274.27 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 17.7099(6) _cell_length_b 6.3908(2) _cell_length_c 11.7770(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.479(2) _cell_angle_gamma 90.00 _cell_volume 1314.73(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5441 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour 'Clear Colourless' _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8772 _exptl_absorpt_correction_T_max 0.9693 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13991 _diffrn_reflns_av_R_equivalents 0.0669 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1505 _reflns_number_gt 1141 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0821P)^2^+0.4729P] 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_extinction_coef ? _refine_ls_number_reflns 1505 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1441 _refine_ls_wR_factor_gt 0.1303 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 O8 O -0.11617(7) 0.70572(16) 0.97024(10) 0.0274(4) Uani 1 1 d . . . O9 O -0.14962(6) 0.39664(17) 1.03853(9) 0.0229(3) Uani 1 1 d . . . N1 N -0.03611(7) 0.4907(2) 0.82325(10) 0.0181(3) Uani 1 1 d . . . C5 C 0.0000 0.1532(3) 0.7500 0.0180(5) Uani 1 2 d S . . C4 C -0.03718(8) 0.0482(2) 0.83066(13) 0.0211(4) Uani 1 1 d . . . C2 C -0.07127(8) 0.3847(2) 0.89617(12) 0.0176(4) Uani 1 1 d . . . C6 C 0.0000 0.3763(3) 0.7500 0.0160(5) Uani 1 2 d S . . C3 C -0.07282(9) 0.1635(2) 0.90412(13) 0.0207(4) Uani 1 1 d . . . C10 C -0.19687(10) 0.5044(3) 1.11048(14) 0.0239(4) Uani 1 1 d . . . C11 C -0.22021(10) 0.3403(3) 1.18941(15) 0.0274(4) Uani 1 1 d . . . C7 C -0.11352(8) 0.5171(2) 0.97140(12) 0.0191(4) Uani 1 1 d . . . H10 H -0.2408(10) 0.565(3) 1.0608(14) 0.022(4) Uiso 1 1 d . . . H11B H -0.1753(12) 0.280(3) 1.2423(18) 0.039(5) Uiso 1 1 d . . . H4 H -0.0372(9) -0.108(4) 0.8336(14) 0.032(5) Uiso 1 1 d . . . H11A H -0.2467(12) 0.221(3) 1.1458(17) 0.032(5) Uiso 1 1 d . . . H10A H -0.1659(11) 0.618(3) 1.1561(16) 0.033(5) Uiso 1 1 d . . . H3 H -0.0994(10) 0.099(3) 0.9608(15) 0.027(5) Uiso 1 1 d . . . H11C H -0.2556(13) 0.402(4) 1.2400(18) 0.047(6) 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 O8 0.0370(7) 0.0173(6) 0.0317(7) 0.0004(4) 0.0167(5) 0.0012(5) O9 0.0285(7) 0.0182(6) 0.0256(6) 0.0003(4) 0.0151(5) -0.0010(4) N1 0.0180(7) 0.0174(6) 0.0196(7) 0.0005(4) 0.0049(5) 0.0002(5) C5 0.0181(11) 0.0156(10) 0.0202(11) 0.000 0.0025(8) 0.000 C4 0.0222(8) 0.0149(8) 0.0267(8) 0.0018(6) 0.0056(6) -0.0005(6) C2 0.0174(7) 0.0172(8) 0.0184(8) -0.0001(5) 0.0037(6) -0.0008(6) C6 0.0174(10) 0.0140(10) 0.0167(10) 0.000 0.0029(8) 0.000 C3 0.0219(8) 0.0175(8) 0.0239(8) 0.0029(6) 0.0071(6) -0.0016(6) C10 0.0259(9) 0.0232(8) 0.0252(9) -0.0006(6) 0.0119(7) 0.0030(7) C11 0.0299(10) 0.0285(9) 0.0259(9) -0.0003(7) 0.0106(7) -0.0049(7) C7 0.0193(8) 0.0195(8) 0.0185(8) 0.0017(5) 0.0035(6) -0.0022(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O8 C7 1.2065(19) . ? O9 C7 1.3388(17) . ? O9 C10 1.4580(17) . ? N1 C2 1.3267(18) . ? N1 C6 1.3676(16) . ? C5 C4 1.4114(17) . ? C5 C4 1.4114(17) 2_556 ? C5 C6 1.426(3) . ? C4 C3 1.367(2) . ? C4 H4 1.00(2) . ? C2 C3 1.418(2) . ? C2 C7 1.509(2) . ? C6 N1 1.3676(16) 2_556 ? C3 H3 0.971(17) . ? C10 C11 1.504(2) . ? C10 H10 0.974(18) . ? C10 H10A 1.01(2) . ? C11 H11B 1.00(2) . ? C11 H11A 0.99(2) . ? C11 H11C 1.01(2) . ? 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 C7 O9 C10 116.56(12) . . ? C2 N1 C6 116.95(14) . . ? C4 C5 C4 123.24(19) . 2_556 ? C4 C5 C6 118.38(9) . . ? C4 C5 C6 118.38(9) 2_556 . ? C3 C4 C5 119.00(15) . . ? C3 C4 H4 121.0(10) . . ? C5 C4 H4 120.0(10) . . ? N1 C2 C3 124.63(13) . . ? N1 C2 C7 115.13(13) . . ? C3 C2 C7 120.22(13) . . ? N1 C6 N1 115.31(18) . 2_556 ? N1 C6 C5 122.34(9) . . ? N1 C6 C5 122.34(9) 2_556 . ? C4 C3 C2 118.67(14) . . ? C4 C3 H3 122.1(11) . . ? C2 C3 H3 119.2(11) . . ? O9 C10 C11 105.81(13) . . ? O9 C10 H10 108.5(9) . . ? C11 C10 H10 112.1(10) . . ? O9 C10 H10A 109.6(11) . . ? C11 C10 H10A 110.6(11) . . ? H10 C10 H10A 110.0(15) . . ? C10 C11 H11B 112.4(12) . . ? C10 C11 H11A 111.8(11) . . ? H11B C11 H11A 106.5(16) . . ? C10 C11 H11C 110.7(13) . . ? H11B C11 H11C 106.7(17) . . ? H11A C11 H11C 108.5(18) . . ? O8 C7 O9 124.03(14) . . ? O8 C7 C2 125.13(13) . . ? O9 C7 C2 110.83(13) . . ? 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 C4 C5 C4 C3 -178.87(15) 2_556 . . . ? C6 C5 C4 C3 1.13(15) . . . . ? C6 N1 C2 C3 1.0(2) . . . . ? C6 N1 C2 C7 -177.19(10) . . . . ? C2 N1 C6 N1 -179.50(13) . . . 2_556 ? C2 N1 C6 C5 0.50(13) . . . . ? C4 C5 C6 N1 -1.55(9) . . . . ? C4 C5 C6 N1 178.45(9) 2_556 . . . ? C4 C5 C6 N1 178.45(9) . . . 2_556 ? C4 C5 C6 N1 -1.55(9) 2_556 . . 2_556 ? C5 C4 C3 C2 0.2(2) . . . . ? N1 C2 C3 C4 -1.4(2) . . . . ? C7 C2 C3 C4 176.72(13) . . . . ? C7 O9 C10 C11 -171.30(13) . . . . ? C10 O9 C7 O8 2.4(2) . . . . ? C10 O9 C7 C2 -176.17(12) . . . . ? N1 C2 C7 O8 -1.0(2) . . . . ? C3 C2 C7 O8 -179.32(15) . . . . ? N1 C2 C7 O9 177.49(12) . . . . ? C3 C2 C7 O9 -0.78(19) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.480 _refine_diff_density_min -0.599 _refine_diff_density_rms 0.217 data_3c _database_code_depnum_ccdc_archive 'CCDC 779574' #TrackingRef '- combined.cif' _chemical_name_systematic ; dibenzyl 1,8-naphthyridine-2,7-dicarboxylate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H18 N2 O4' _chemical_formula_sum 'C24 H18 N2 O4' _chemical_formula_weight 398.40 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 'C 2/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 35.50(4) _cell_length_b 6.307(8) _cell_length_c 8.381(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.849(13) _cell_angle_gamma 90.00 _cell_volume 1872(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 967 _cell_measurement_theta_min 3.37 _cell_measurement_theta_max 27.95 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.005 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.6939 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 8192 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0510 _diffrn_reflns_limit_h_min -46 _diffrn_reflns_limit_h_max 46 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2305 _reflns_number_gt 1682 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0731P)^2^+0.2853P] 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_extinction_coef ? _refine_ls_number_reflns 2305 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1328 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 O9 O 0.60679(3) 0.90138(17) -0.03904(14) 0.0275(3) Uani 1 1 d . . . N1 N 0.52554(3) 0.9933(2) 0.17178(15) 0.0235(3) Uani 1 1 d . . . O8 O 0.57558(3) 1.20835(17) -0.01119(14) 0.0303(3) Uani 1 1 d . . . C5 C 0.5000 0.6513(3) 0.2500 0.0232(4) Uani 1 2 d S . . C2 C 0.55058(4) 0.8859(2) 0.09402(19) 0.0233(3) Uani 1 1 d . . . C6 C 0.5000 0.8771(3) 0.2500 0.0216(4) Uani 1 2 d S . . C4 C 0.52737(4) 0.5447(2) 0.16545(19) 0.0263(4) Uani 1 1 d . . . C11 C 0.65825(4) 0.8536(2) -0.20653(19) 0.0255(3) Uani 1 1 d . . . C3 C 0.55269(4) 0.6615(2) 0.0871(2) 0.0262(3) Uani 1 1 d . . . C10 C 0.63459(5) 1.0138(3) -0.1260(2) 0.0264(4) Uani 1 1 d . . . C12 C 0.64412(5) 0.6556(3) -0.2560(2) 0.0282(4) Uani 1 1 d . . . C7 C 0.57818(4) 1.0205(2) 0.00965(18) 0.0237(3) Uani 1 1 d . . . C13 C 0.66615(5) 0.5177(3) -0.3400(2) 0.0330(4) Uani 1 1 d . . . C15 C 0.71666(5) 0.7699(3) -0.3258(2) 0.0364(4) Uani 1 1 d . . . C16 C 0.69480(5) 0.9080(3) -0.2409(2) 0.0316(4) Uani 1 1 d . . . C14 C 0.70222(5) 0.5754(3) -0.3759(2) 0.0356(4) Uani 1 1 d . . . H12 H 0.6185(5) 0.617(3) -0.232(2) 0.029(5) Uiso 1 1 d . . . H10A H 0.6199(5) 1.102(3) -0.206(2) 0.037(5) Uiso 1 1 d . . . H4 H 0.5279(4) 0.389(3) 0.161(2) 0.027(5) Uiso 1 1 d . . . H14 H 0.7160(5) 0.479(3) -0.432(2) 0.038(5) Uiso 1 1 d . . . H15 H 0.7424(6) 0.810(3) -0.347(3) 0.047(6) Uiso 1 1 d . . . H3 H 0.5722(5) 0.596(3) 0.027(2) 0.032(5) Uiso 1 1 d . . . H10B H 0.6502(5) 1.104(3) -0.050(2) 0.035(5) Uiso 1 1 d . . . H16 H 0.7046(5) 1.051(3) -0.207(2) 0.033(5) Uiso 1 1 d . . . H13 H 0.6565(6) 0.388(3) -0.376(2) 0.043(6) 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 O9 0.0278(6) 0.0215(5) 0.0347(7) 0.0034(4) 0.0120(5) 0.0021(4) N1 0.0240(7) 0.0192(6) 0.0277(7) 0.0001(5) 0.0034(5) 0.0008(5) O8 0.0334(6) 0.0197(6) 0.0388(7) 0.0001(5) 0.0104(5) -0.0004(5) C5 0.0242(11) 0.0186(10) 0.0268(11) 0.000 0.0011(8) 0.000 C2 0.0243(8) 0.0192(7) 0.0266(8) 0.0004(6) 0.0027(6) 0.0008(6) C6 0.0231(10) 0.0164(10) 0.0254(11) 0.000 0.0015(8) 0.000 C4 0.0290(8) 0.0174(7) 0.0326(9) -0.0010(6) 0.0029(6) 0.0018(6) C11 0.0281(8) 0.0247(8) 0.0240(7) 0.0016(6) 0.0035(6) 0.0018(6) C3 0.0269(8) 0.0209(7) 0.0310(8) -0.0026(6) 0.0046(6) 0.0030(6) C10 0.0268(8) 0.0234(8) 0.0296(9) 0.0003(6) 0.0075(7) -0.0014(6) C12 0.0304(9) 0.0264(8) 0.0281(8) 0.0004(6) 0.0040(6) -0.0007(7) C7 0.0259(8) 0.0199(7) 0.0255(8) -0.0019(6) 0.0023(6) 0.0004(6) C13 0.0424(10) 0.0256(8) 0.0312(9) -0.0008(7) 0.0041(7) 0.0004(7) C15 0.0277(9) 0.0406(10) 0.0418(10) -0.0011(8) 0.0081(7) 0.0035(7) C16 0.0282(9) 0.0298(9) 0.0375(10) -0.0016(7) 0.0062(7) -0.0013(7) C14 0.0398(10) 0.0341(9) 0.0338(9) -0.0013(7) 0.0095(7) 0.0109(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O9 C7 1.348(2) . ? O9 C10 1.450(2) . ? N1 C2 1.323(2) . ? N1 C6 1.3671(19) . ? O8 C7 1.200(2) . ? C5 C4 1.411(2) . ? C5 C4 1.411(2) 2_655 ? C5 C6 1.424(3) . ? C2 C3 1.419(3) . ? C2 C7 1.508(2) . ? C6 N1 1.3671(19) 2_655 ? C4 C3 1.364(2) . ? C4 H4 0.982(18) . ? C11 C16 1.391(3) . ? C11 C12 1.398(3) . ? C11 C10 1.503(2) . ? C3 H3 0.976(18) . ? C10 H10A 0.990(19) . ? C10 H10B 0.993(19) . ? C12 C13 1.392(3) . ? C12 H12 0.977(17) . ? C13 C14 1.383(3) . ? C13 H13 0.93(2) . ? C15 C14 1.384(3) . ? C15 C16 1.394(3) . ? C15 H15 0.98(2) . ? C16 H16 1.003(19) . ? C14 H14 0.926(19) . ? 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 C7 O9 C10 115.56(14) . . ? C2 N1 C6 116.79(15) . . ? C4 C5 C4 123.1(2) . 2_655 ? C4 C5 C6 118.44(10) . . ? C4 C5 C6 118.44(10) 2_655 . ? N1 C2 C3 124.75(14) . . ? N1 C2 C7 114.96(15) . . ? C3 C2 C7 120.28(14) . . ? N1 C6 N1 115.16(19) 2_655 . ? N1 C6 C5 122.42(10) 2_655 . ? N1 C6 C5 122.42(10) . . ? C3 C4 C5 118.90(16) . . ? C3 C4 H4 120.6(10) . . ? C5 C4 H4 120.5(10) . . ? C16 C11 C12 118.69(15) . . ? C16 C11 C10 118.98(15) . . ? C12 C11 C10 122.24(16) . . ? C4 C3 C2 118.70(15) . . ? C4 C3 H3 122.2(11) . . ? C2 C3 H3 119.1(11) . . ? O9 C10 C11 108.46(15) . . ? O9 C10 H10A 105.6(11) . . ? C11 C10 H10A 110.9(11) . . ? O9 C10 H10B 109.1(11) . . ? C11 C10 H10B 111.5(11) . . ? H10A C10 H10B 111.0(15) . . ? C13 C12 C11 120.37(17) . . ? C13 C12 H12 120.6(10) . . ? C11 C12 H12 119.1(10) . . ? O8 C7 O9 123.91(15) . . ? O8 C7 C2 125.29(14) . . ? O9 C7 C2 110.79(15) . . ? C14 C13 C12 120.33(18) . . ? C14 C13 H13 119.1(12) . . ? C12 C13 H13 120.6(13) . . ? C14 C15 C16 120.07(18) . . ? C14 C15 H15 120.5(12) . . ? C16 C15 H15 119.4(12) . . ? C11 C16 C15 120.73(17) . . ? C11 C16 H16 118.3(10) . . ? C15 C16 H16 120.9(10) . . ? C15 C14 C13 119.80(16) . . ? C15 C14 H14 122.5(12) . . ? C13 C14 H14 117.7(12) . . ? 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 N1 C2 C3 -0.2(2) . . . . ? C6 N1 C2 C7 -179.97(11) . . . . ? C2 N1 C6 N1 -179.65(15) . . . 2_655 ? C2 N1 C6 C5 0.35(15) . . . . ? C4 C5 C6 N1 179.78(10) . . . 2_655 ? C4 C5 C6 N1 -0.22(10) 2_655 . . 2_655 ? C4 C5 C6 N1 -0.22(10) . . . . ? C4 C5 C6 N1 179.78(10) 2_655 . . . ? C4 C5 C4 C3 179.95(17) 2_655 . . . ? C6 C5 C4 C3 -0.05(17) . . . . ? C5 C4 C3 C2 0.2(2) . . . . ? N1 C2 C3 C4 0.0(3) . . . . ? C7 C2 C3 C4 179.69(15) . . . . ? C7 O9 C10 C11 -165.66(13) . . . . ? C16 C11 C10 O9 -154.15(15) . . . . ? C12 C11 C10 O9 29.4(2) . . . . ? C16 C11 C12 C13 -0.9(2) . . . . ? C10 C11 C12 C13 175.55(16) . . . . ? C10 O9 C7 O8 -2.2(2) . . . . ? C10 O9 C7 C2 178.33(13) . . . . ? N1 C2 C7 O8 -11.5(2) . . . . ? C3 C2 C7 O8 168.71(16) . . . . ? N1 C2 C7 O9 167.95(13) . . . . ? C3 C2 C7 O9 -11.8(2) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C12 C11 C16 C15 1.3(3) . . . . ? C10 C11 C16 C15 -175.26(16) . . . . ? C14 C15 C16 C11 -0.6(3) . . . . ? C16 C15 C14 C13 -0.6(3) . . . . ? C12 C13 C14 C15 1.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.357 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.047 data_3d _database_code_depnum_ccdc_archive 'CCDC 779575' #TrackingRef '- combined.cif' loop_ _chemical_name_systematic ; di-2-(pyridyl)methyl 1,8-naphthyridine-2,7-dicarboxylate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 N4 O4' _chemical_formula_sum 'C22 H16 N4 O4' _chemical_formula_weight 400.39 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 5.0497(3) _cell_length_b 28.8108(15) _cell_length_c 6.3242(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 920.08(9) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8993 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Needle _exptl_crystal_colour 'Clear Colourless' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5325 _exptl_absorpt_correction_T_max 0.7297 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 4793 reflections reduced R(int) from 0.2794 to 0.0643 Ratio of minimum to maximum apparent transmission: 0.729737 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5825 _diffrn_reflns_av_R_equivalents 0.0770 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1285 _reflns_number_gt 937 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution SIR2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0100P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1285 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1268 _refine_ls_R_factor_gt 0.0854 _refine_ls_wR_factor_ref 0.1296 _refine_ls_wR_factor_gt 0.1211 _refine_ls_goodness_of_fit_ref 1.831 _refine_ls_restrained_S_all 1.831 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 O8 O -0.4933(6) -0.08807(9) -1.6593(4) 0.0299(8) Uani 1 1 d . . . O9 O -0.6887(6) -0.10674(9) -1.3534(5) 0.0241(8) Uani 1 1 d . . . N1 N -0.1675(7) -0.02716(11) -1.4431(5) 0.0191(9) Uani 1 1 d . . . N12 N -1.2062(8) -0.19182(12) -1.4078(6) 0.0267(10) Uani 1 1 d . . . C2 C -0.3364(9) -0.05350(14) -1.3369(7) 0.0219(10) Uani 1 1 d . . . C3 C -0.3518(9) -0.05516(14) -1.1158(7) 0.0217(11) Uani 1 1 d . . . H3 H -0.4753 -0.0743 -1.0504 0.026 Uiso 1 1 calc R . . C4 C -0.1840(8) -0.02840(14) -0.9959(7) 0.0231(10) Uani 1 1 d . . . H4 H -0.1915 -0.0290 -0.8489 0.028 Uiso 1 1 calc R . . C5 C 0.0000 0.0000 -1.1030(9) 0.0186(14) Uani 1 2 d S . . C6 C 0.0000 0.0000 -1.3262(10) 0.0198(14) Uani 1 2 d S . . C7 C -0.5093(9) -0.08370(14) -1.4718(7) 0.0224(10) Uani 1 1 d . . . C10 C -0.8610(9) -0.13805(14) -1.4690(6) 0.0234(11) Uani 1 1 d . . . H10A H -0.7559 -0.1607 -1.5450 0.028 Uiso 1 1 calc R . . H10B H -0.9652 -0.1207 -1.5709 0.028 Uiso 1 1 calc R . . C11 C -1.0409(9) -0.16214(13) -1.3153(7) 0.0214(11) Uani 1 1 d . . . C13 C -1.3814(10) -0.21395(15) -1.2814(8) 0.0290(13) Uani 1 1 d . . . H13 H -1.4987 -0.2348 -1.3434 0.035 Uiso 1 1 calc R . . C14 C -1.3959(10) -0.20729(14) -1.0649(8) 0.0265(13) Uani 1 1 d . . . H14 H -1.5217 -0.2230 -0.9846 0.032 Uiso 1 1 calc R . . C15 C -1.2206(9) -0.17704(14) -0.9702(7) 0.0240(11) Uani 1 1 d . . . H15 H -1.2243 -0.1721 -0.8250 0.029 Uiso 1 1 calc R . . C16 C -1.0379(10) -0.15416(14) -1.0979(7) 0.0244(11) Uani 1 1 d . . . H16 H -0.9155 -0.1338 -1.0390 0.029 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 O8 0.039(2) 0.0369(18) 0.0134(15) -0.0013(14) 0.0002(18) -0.0188(18) O9 0.0242(18) 0.0279(17) 0.0202(16) -0.0039(14) 0.0005(16) -0.0105(15) N1 0.021(2) 0.0191(18) 0.018(2) -0.0026(15) -0.0007(18) -0.0016(18) N12 0.027(2) 0.0220(19) 0.031(2) 0.0043(17) 0.0026(19) -0.0050(19) C2 0.023(3) 0.023(2) 0.020(2) 0.0026(19) 0.001(2) -0.002(2) C3 0.021(3) 0.018(2) 0.027(3) -0.001(2) -0.006(2) -0.004(2) C4 0.024(3) 0.024(2) 0.021(2) 0.003(2) 0.005(2) 0.002(2) C5 0.020(4) 0.013(3) 0.022(3) 0.000 0.000 -0.003(3) C6 0.017(3) 0.018(3) 0.024(3) 0.000 0.000 0.003(3) C7 0.026(3) 0.021(2) 0.021(2) 0.002(2) -0.001(2) -0.004(2) C10 0.026(3) 0.027(2) 0.017(2) -0.0044(19) 0.000(2) -0.007(2) C11 0.019(3) 0.016(2) 0.030(3) 0.002(2) 0.000(2) 0.002(2) C13 0.024(3) 0.020(3) 0.043(3) -0.002(2) -0.007(3) -0.002(2) C14 0.021(3) 0.021(2) 0.038(3) 0.004(2) 0.005(2) 0.002(2) C15 0.026(3) 0.025(2) 0.021(3) 0.0007(19) 0.002(2) 0.002(2) C16 0.026(3) 0.019(2) 0.028(3) -0.002(2) -0.001(2) -0.001(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O8 C7 1.195(5) . ? O9 C7 1.350(5) . ? O9 C10 1.451(4) . ? N1 C2 1.325(5) . ? N1 C6 1.369(4) . ? N12 C11 1.331(5) . ? N12 C13 1.352(6) . ? C2 C3 1.401(6) . ? C2 C7 1.499(6) . ? C3 C4 1.374(5) . ? C3 H3 0.9300 . ? C4 C5 1.412(5) . ? C4 H4 0.9300 . ? C5 C4 1.412(5) 2 ? C5 C6 1.411(8) . ? C6 N1 1.369(4) 2 ? C10 C11 1.501(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C16 1.394(6) . ? C13 C14 1.385(6) . ? C13 H13 0.9300 . ? C14 C15 1.379(6) . ? C14 H14 0.9300 . ? C15 C16 1.392(6) . ? C15 H15 0.9300 . ? C16 H16 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 C7 O9 C10 115.4(3) . . ? C2 N1 C6 116.8(4) . . ? C11 N12 C13 117.0(4) . . ? N1 C2 C3 124.2(4) . . ? N1 C2 C7 114.7(4) . . ? C3 C2 C7 121.1(4) . . ? C4 C3 C2 119.8(4) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 117.8(4) . . ? C3 C4 H4 121.1 . . ? C5 C4 H4 121.1 . . ? C4 C5 C4 122.6(6) 2 . ? C4 C5 C6 118.7(3) 2 . ? C4 C5 C6 118.7(3) . . ? N1 C6 N1 114.6(5) 2 . ? N1 C6 C5 122.7(3) 2 . ? N1 C6 C5 122.7(3) . . ? O8 C7 O9 123.0(4) . . ? O8 C7 C2 125.9(4) . . ? O9 C7 C2 111.1(3) . . ? O9 C10 C11 108.9(3) . . ? O9 C10 H10A 109.9 . . ? C11 C10 H10A 109.9 . . ? O9 C10 H10B 109.9 . . ? C11 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? N12 C11 C16 123.1(4) . . ? N12 C11 C10 113.1(4) . . ? C16 C11 C10 123.8(4) . . ? N12 C13 C14 123.6(5) . . ? N12 C13 H13 118.2 . . ? C14 C13 H13 118.2 . . ? C15 C14 C13 118.9(5) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C14 C15 C16 118.2(4) . . ? C14 C15 H15 120.9 . . ? C16 C15 H15 120.9 . . ? C15 C16 C11 119.1(5) . . ? C15 C16 H16 120.4 . . ? C11 C16 H16 120.4 . . ? 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 N1 C2 C3 -0.3(6) . . . . ? C6 N1 C2 C7 -178.1(3) . . . . ? N1 C2 C3 C4 -0.2(7) . . . . ? C7 C2 C3 C4 177.5(4) . . . . ? C2 C3 C4 C5 -0.1(6) . . . . ? C3 C4 C5 C4 -179.1(4) . . . 2 ? C3 C4 C5 C6 0.9(4) . . . . ? C2 N1 C6 N1 -178.9(4) . . . 2 ? C2 N1 C6 C5 1.1(4) . . . . ? C4 C5 C6 N1 -1.4(3) 2 . . 2 ? C4 C5 C6 N1 178.6(3) . . . 2 ? C4 C5 C6 N1 178.6(3) 2 . . . ? C4 C5 C6 N1 -1.4(3) . . . . ? C10 O9 C7 O8 0.8(6) . . . . ? C10 O9 C7 C2 -178.3(3) . . . . ? N1 C2 C7 O8 5.6(7) . . . . ? C3 C2 C7 O8 -172.3(4) . . . . ? N1 C2 C7 O9 -175.4(3) . . . . ? C3 C2 C7 O9 6.7(6) . . . . ? C7 O9 C10 C11 177.9(3) . . . . ? C13 N12 C11 C16 1.6(7) . . . . ? C13 N12 C11 C10 -177.9(4) . . . . ? O9 C10 C11 N12 -179.8(4) . . . . ? O9 C10 C11 C16 0.8(6) . . . . ? C11 N12 C13 C14 -0.1(7) . . . . ? N12 C13 C14 C15 -1.0(7) . . . . ? C13 C14 C15 C16 0.6(6) . . . . ? C14 C15 C16 C11 0.8(6) . . . . ? N12 C11 C16 C15 -1.9(7) . . . . ? C10 C11 C16 C15 177.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.420 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.085 data_4 _database_code_depnum_ccdc_archive 'CCDC 779576' #TrackingRef '- combined.cif' _chemical_name_systematic ; 2,7-dimethyl-1,8-naphthyridine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 N2' _chemical_formula_sum 'C10 H10 N2' _chemical_formula_weight 158.20 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 13.4667(6) _cell_length_b 19.3913(10) _cell_length_c 6.3165(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1649.47(14) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2750 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Prism _exptl_crystal_colour 'Clear Colourless' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8588 _exptl_absorpt_correction_T_max 0.9693 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5363 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 27.49 _reflns_number_total 518 _reflns_number_gt 439 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0772P)^2^+0.2908P] 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 0.017(3) _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 ? _refine_ls_number_reflns 518 _refine_ls_number_parameters 58 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1215 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.143 _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 N1 N 0.01022(12) 0.44076(7) 0.8045(2) 0.0224(6) Uani 1 1 d . . . C5 C 0.0000 0.5000 0.4652(5) 0.0214(7) Uani 1 2 d S . . C3 C 0.02122(17) 0.37777(11) 0.4762(4) 0.0259(6) Uani 1 1 d . . . H3 H 0.0287 0.3353 0.4098 0.031 Uiso 1 1 calc R . . C7 C 0.02681(15) 0.31676(10) 0.8292(4) 0.0283(6) Uani 1 1 d . . . H7A H 0.0387 0.3282 0.9748 0.043 Uiso 1 1 calc R . . H7B H 0.0805 0.2890 0.7770 0.043 Uiso 1 1 calc R . . H7C H -0.0343 0.2915 0.8178 0.043 Uiso 1 1 calc R . . C6 C 0.0000 0.5000 0.6893(4) 0.0188(8) Uani 1 2 d S . . C2 C 0.01971(16) 0.38157(10) 0.7012(3) 0.0221(7) Uani 1 1 d . . . C4 C 0.01180(14) 0.43603(9) 0.3582(3) 0.0233(6) Uani 1 1 d . . . H4 H 0.0130 0.4341 0.2111 0.028 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 0.0263(11) 0.0210(12) 0.0199(11) 0.0014(7) 0.0019(8) -0.0005(7) C5 0.0210(16) 0.0252(19) 0.0182(16) 0.000 0.000 -0.0006(12) C3 0.0269(15) 0.0245(13) 0.0262(12) -0.0061(9) 0.0010(10) -0.0003(9) C7 0.0335(11) 0.0217(11) 0.0298(12) 0.0034(9) 0.0018(11) 0.0003(8) C6 0.0200(17) 0.0203(19) 0.0160(18) 0.000 0.000 -0.0003(11) C2 0.0221(14) 0.0211(14) 0.0232(15) 0.0022(9) 0.0003(9) -0.0001(8) C4 0.0238(12) 0.0285(12) 0.0175(12) -0.0017(10) 0.0009(9) 0.0007(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.327(2) . ? N1 C6 1.367(2) . ? C5 C6 1.416(4) . ? C5 C4 1.421(2) . ? C5 C4 1.421(2) 2_565 ? C3 C4 1.359(3) . ? C3 C2 1.423(3) . ? C3 H3 0.9300 . ? C7 C2 1.497(3) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C6 N1 1.367(2) 2_565 ? C4 H4 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 C2 N1 C6 118.34(16) . . ? C6 C5 C4 118.39(14) . . ? C6 C5 C4 118.39(14) . 2_565 ? C4 C5 C4 123.2(3) . 2_565 ? C4 C3 C2 120.22(19) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C6 N1 115.6(2) 2_565 . ? N1 C6 C5 122.18(10) 2_565 . ? N1 C6 C5 122.18(10) . . ? N1 C2 C3 122.51(19) . . ? N1 C2 C7 117.82(15) . . ? C3 C2 C7 119.66(19) . . ? C3 C4 C5 118.3(2) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? 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 C2 N1 C6 N1 179.53(19) . . . 2_565 ? C2 N1 C6 C5 -0.47(19) . . . . ? C4 C5 C6 N1 179.53(14) . . . 2_565 ? C4 C5 C6 N1 -0.47(14) 2_565 . . 2_565 ? C4 C5 C6 N1 -0.47(14) . . . . ? C4 C5 C6 N1 179.53(14) 2_565 . . . ? C6 N1 C2 C3 1.0(3) . . . . ? C6 N1 C2 C7 -177.64(14) . . . . ? C4 C3 C2 N1 -0.6(4) . . . . ? C4 C3 C2 C7 178.01(17) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C6 C5 C4 C3 0.8(2) . . . . ? C4 C5 C4 C3 -179.2(2) 2_565 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.408 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.228