Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_section_title ;A Competition Between N---O and C---O Through Space Interactions in the Crystal Structures of 3,3'-Dinitro-2,2'-bipyridine N-Oxides and N,N'-Dioxides ; _publ_contact_author_name 'Prof. John Wallis' _publ_contact_author_email JOHN.WALLIS@NTU.AC.UK loop_ _publ_author_name J.Wallis "Jane O'Leary" # Attachment 'WALLIS_CIFS_B707822F.txt' data_compound13 _database_code_depnum_ccdc_archive 'CCDC 648398' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,3'-dinitro-2,2'-bipyridine-1-oxide ; _chemical_name_common 3,3'-dinitro-2,2'-bipyridine-1-oxide _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H6 N4 O5' _chemical_formula_weight 262.19 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/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 9.873(2) _cell_length_b 10.671(2) _cell_length_c 10.578(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.58(3) _cell_angle_gamma 90.00 _cell_volume 1078.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 15743 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour 'pale green' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details ; using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) See R.H. Blessing, Acta Cryst., (1995), A51, 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8399 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2430 _reflns_number_gt 1820 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_cell_refinement ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_data_reduction ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0784P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2430 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1228 _refine_ls_wR_factor_gt 0.1145 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 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 O1A O 0.01209(12) 0.04964(10) 0.32894(10) 0.0381(3) Uani 1 1 d . . . O2A O 0.20012(14) 0.42957(12) 0.17051(12) 0.0498(4) Uani 1 1 d . . . O3A O 0.17610(14) 0.57008(11) 0.31024(12) 0.0504(4) Uani 1 1 d . . . N1A N 0.04996(12) 0.16049(11) 0.37634(11) 0.0266(3) Uani 1 1 d . . . N2A N 0.17115(14) 0.46173(13) 0.27105(13) 0.0358(3) Uani 1 1 d . . . C2A C 0.08516(14) 0.24952(13) 0.29721(13) 0.0251(3) Uani 1 1 d . . . C3A C 0.12931(15) 0.36484(14) 0.35242(15) 0.0288(4) Uani 1 1 d . . . C4A C 0.13733(17) 0.39277(16) 0.48086(16) 0.0349(4) Uani 1 1 d . . . C5A C 0.09815(18) 0.30035(16) 0.55589(16) 0.0360(4) Uani 1 1 d . . . C6A C 0.05527(16) 0.18606(15) 0.50338(14) 0.0322(4) Uani 1 1 d . . . O2B O 0.31126(11) 0.11713(12) 0.30610(11) 0.0402(3) Uani 1 1 d . . . O3B O 0.30988(12) -0.02618(12) 0.16098(13) 0.0479(4) Uani 1 1 d . . . N1B N -0.04755(12) 0.27067(12) 0.07786(11) 0.0293(3) Uani 1 1 d . . . N2B N 0.26371(12) 0.06955(13) 0.19819(13) 0.0321(3) Uani 1 1 d . . . C2B C 0.06295(14) 0.21516(13) 0.15711(13) 0.0243(3) Uani 1 1 d . . . C3B C 0.14565(14) 0.13131(13) 0.10929(14) 0.0261(3) Uani 1 1 d . . . C4B C 0.11717(16) 0.10426(15) -0.02201(15) 0.0307(4) Uani 1 1 d . . . C5B C 0.00576(16) 0.16432(15) -0.10336(16) 0.0317(4) Uani 1 1 d . . . C6B C -0.07348(17) 0.24556(15) -0.05000(15) 0.0318(4) Uani 1 1 d . . . H4A H 0.1673(17) 0.4712(18) 0.5142(16) 0.041(5) Uiso 1 1 d . . . H5A H 0.103(2) 0.3142(18) 0.643(2) 0.054(6) Uiso 1 1 d . . . H6A H 0.0273(17) 0.1186(15) 0.5495(16) 0.033(4) Uiso 1 1 d . . . H4B H 0.1690(18) 0.0437(16) -0.0523(16) 0.034(4) Uiso 1 1 d . . . H5B H -0.0177(18) 0.1477(16) -0.1983(19) 0.044(5) Uiso 1 1 d . . . H6B H -0.1527(17) 0.2894(15) -0.1045(15) 0.031(4) 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 O1A 0.0578(7) 0.0256(6) 0.0342(6) -0.0033(5) 0.0177(5) -0.0124(5) O2A 0.0639(8) 0.0474(8) 0.0441(8) 0.0032(6) 0.0246(6) -0.0202(6) O3A 0.0687(9) 0.0270(7) 0.0496(8) 0.0034(6) 0.0038(6) -0.0130(6) N1A 0.0323(7) 0.0234(7) 0.0258(7) -0.0001(5) 0.0107(5) -0.0035(5) N2A 0.0381(7) 0.0300(8) 0.0353(8) 0.0039(6) 0.0017(6) -0.0112(6) C2A 0.0259(7) 0.0251(8) 0.0250(8) 0.0022(6) 0.0077(6) -0.0003(5) C3A 0.0298(8) 0.0252(8) 0.0307(8) 0.0026(6) 0.0061(6) -0.0034(6) C4A 0.0415(9) 0.0286(9) 0.0316(9) -0.0029(7) 0.0031(7) -0.0022(7) C5A 0.0466(9) 0.0363(10) 0.0238(8) -0.0044(7) 0.0065(7) -0.0012(7) C6A 0.0402(9) 0.0326(9) 0.0261(8) 0.0033(7) 0.0125(6) -0.0006(7) O2B 0.0311(6) 0.0575(8) 0.0317(6) 0.0099(5) 0.0071(5) 0.0031(5) O3B 0.0434(7) 0.0377(7) 0.0650(9) 0.0087(6) 0.0181(6) 0.0149(5) N1B 0.0321(7) 0.0309(7) 0.0261(7) 0.0031(5) 0.0098(5) 0.0040(5) N2B 0.0272(7) 0.0326(8) 0.0398(8) 0.0103(6) 0.0145(6) 0.0029(5) C2B 0.0258(7) 0.0236(8) 0.0248(7) 0.0031(6) 0.0085(6) -0.0032(5) C3B 0.0250(7) 0.0257(8) 0.0294(8) 0.0056(6) 0.0100(6) -0.0007(5) C4B 0.0346(8) 0.0279(9) 0.0350(9) -0.0004(7) 0.0189(6) -0.0004(6) C5B 0.0384(9) 0.0332(9) 0.0257(8) -0.0003(6) 0.0123(6) -0.0028(6) C6B 0.0351(8) 0.0354(9) 0.0246(8) 0.0037(7) 0.0069(6) 0.0040(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 O1A N1A 1.3023(16) . ? O2A N2A 1.2181(17) . ? O3A N2A 1.2251(17) . ? N1A C6A 1.3592(19) . ? N1A C2A 1.3677(19) . ? N2A C3A 1.4695(19) . ? C2A C3A 1.385(2) . ? C2A C2B 1.488(2) . ? C3A C4A 1.374(2) . ? C4A C5A 1.381(2) . ? C5A C6A 1.363(2) . ? O2B N2B 1.2293(17) . ? O3B N2B 1.2233(18) . ? N1B C2B 1.3353(18) . ? N1B C6B 1.339(2) . ? N2B C3B 1.4578(19) . ? C2B C3B 1.390(2) . ? C3B C4B 1.377(2) . ? C4B C5B 1.373(2) . ? C5B C6B 1.380(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 O1A N1A C6A 119.93(12) . . ? O1A N1A C2A 119.20(12) . . ? C6A N1A C2A 120.87(13) . . ? O2A N2A O3A 124.27(14) . . ? O2A N2A C3A 118.40(14) . . ? O3A N2A C3A 117.32(14) . . ? N1A C2A C3A 117.43(13) . . ? N1A C2A C2B 116.22(12) . . ? C3A C2A C2B 126.21(13) . . ? C4A C3A C2A 122.93(14) . . ? C4A C3A N2A 118.16(14) . . ? C2A C3A N2A 118.90(14) . . ? C3A C4A C5A 117.31(16) . . ? C6A C5A C4A 120.55(15) . . ? N1A C6A C5A 120.89(14) . . ? C2B N1B C6B 117.62(12) . . ? O3B N2B O2B 123.88(13) . . ? O3B N2B C3B 118.17(13) . . ? O2B N2B C3B 117.95(13) . . ? N1B C2B C3B 121.27(13) . . ? N1B C2B C2A 114.09(12) . . ? C3B C2B C2A 124.63(12) . . ? C4B C3B C2B 120.85(13) . . ? C4B C3B N2B 118.89(13) . . ? C2B C3B N2B 120.26(13) . . ? C5B C4B C3B 117.54(14) . . ? C4B C5B C6B 118.96(15) . . ? N1B C6B C5B 123.71(15) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.280 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.055 data_compound14 _database_code_depnum_ccdc_archive 'CCDC 648399' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,3-Dinitro-2,2-bipyridine-1,1-dioxide ; _chemical_name_common 3,3-Dinitro-2,2-bipyridine-1,1-dioxide _chemical_melting_point 475-479 _chemical_formula_moiety ? _chemical_formula_sum 'C10 H6 N4 O6' _chemical_formula_weight 278.19 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1226(3) _cell_length_b 7.4847(4) _cell_length_c 13.5200(8) _cell_angle_alpha 102.8252(2) _cell_angle_beta 90.226(2) _cell_angle_gamma 111.154(3) _cell_volume 560.99(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2075 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.647 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.935 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details ; using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) See R.H. Blessing, Acta Cryst., (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relecvant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. Some additional spots are observed, indexing suggests a much larger cell, a = 20.3578, b = c = 22.7139 Angstroms, alpha = 89.5742, beta = 87.1617, gamma = 74.5216 degrees. The refinement with the smaller cell provides a reasonable structural model but with some elongations of the thermal ellipsoids. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6412 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1916 _reflns_number_gt 1279 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_cell_refinement ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_data_reduction ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0736P)^2^+0.4046P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1916 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0970 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.1578 _refine_ls_wR_factor_gt 0.1398 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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 O1B O 0.2045(4) 0.3669(3) 0.35908(17) 0.0360(6) Uani 1 1 d . . . O2A O -0.2708(4) 0.1602(4) 0.2426(2) 0.0581(8) Uani 1 1 d . . . O3A O -0.3598(4) 0.2072(4) 0.3997(2) 0.0674(10) Uani 1 1 d . . . N1B N 0.2392(4) 0.2908(3) 0.26718(19) 0.0279(6) Uani 1 1 d . . . N2A N -0.2755(5) 0.1293(4) 0.3282(3) 0.0474(9) Uani 1 1 d . . . C2A C 0.0143(5) -0.0305(4) 0.2981(2) 0.0290(7) Uani 1 1 d . . . C3A C -0.1778(5) -0.0146(4) 0.3479(3) 0.0310(8) Uani 1 1 d . . . C4A C -0.2873(6) -0.1319(4) 0.4117(3) 0.0351(8) Uani 1 1 d . . . C5A C -0.2024(6) -0.2738(5) 0.4234(3) 0.0352(8) Uani 1 1 d . . . C6A C -0.0124(6) -0.2912(4) 0.3756(3) 0.0401(9) Uani 1 1 d . . . O1A O 0.2771(4) -0.1896(3) 0.2686(2) 0.0579(8) Uani 1 1 d . . . O2B O -0.1217(5) -0.2876(4) 0.1082(2) 0.0727(10) Uani 1 1 d . . . O3B O 0.1784(9) -0.2695(5) 0.0206(4) 0.164(3) Uani 1 1 d . . . N1A N 0.0969(4) -0.1701(3) 0.3141(2) 0.0367(7) Uani 1 1 d . . . N2B N 0.0734(7) -0.1979(5) 0.0834(3) 0.0833(14) Uani 1 1 d . . . C2B C 0.1441(5) 0.0902(4) 0.2289(3) 0.0313(8) Uani 1 1 d . . . C3B C 0.1835(6) 0.0160(5) 0.1296(3) 0.0491(10) Uani 1 1 d . . . C4B C 0.3176(7) 0.1332(6) 0.0702(3) 0.0597(12) Uani 1 1 d . . . C5B C 0.4085(6) 0.3353(5) 0.1124(3) 0.0443(9) Uani 1 1 d . . . C6B C 0.3663(5) 0.4106(5) 0.2083(3) 0.0329(8) Uani 1 1 d . . . H4A H -0.420(6) -0.118(5) 0.441(2) 0.042(9) Uiso 1 1 d . . . H5A H -0.271(6) -0.355(5) 0.466(3) 0.046(10) Uiso 1 1 d . . . H6A H 0.054(6) -0.391(6) 0.376(3) 0.055(10) Uiso 1 1 d . . . H4B H 0.335(8) 0.075(6) 0.002(3) 0.079(14) Uiso 1 1 d . . . H5B H 0.505(7) 0.424(6) 0.071(3) 0.059(11) Uiso 1 1 d . . . H6B H 0.422(6) 0.548(5) 0.240(2) 0.042(9) 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 O1B 0.0366(13) 0.0254(11) 0.0538(15) 0.0159(10) 0.0183(11) 0.0168(10) O2A 0.0271(13) 0.0598(17) 0.113(2) 0.0636(17) 0.0231(14) 0.0204(12) O3A 0.0512(16) 0.0384(15) 0.137(3) 0.0393(16) 0.0567(18) 0.0335(14) N1B 0.0203(13) 0.0204(13) 0.0499(17) 0.0187(12) 0.0099(12) 0.0095(11) N2A 0.0238(15) 0.0305(15) 0.105(3) 0.0363(17) 0.0332(17) 0.0178(13) C2A 0.0215(16) 0.0178(15) 0.053(2) 0.0153(14) 0.0141(14) 0.0088(13) C3A 0.0203(15) 0.0183(15) 0.060(2) 0.0171(15) 0.0161(15) 0.0096(13) C4A 0.0271(17) 0.0243(16) 0.058(2) 0.0170(15) 0.0248(16) 0.0099(14) C5A 0.0300(18) 0.0226(16) 0.055(2) 0.0212(16) 0.0113(16) 0.0052(14) C6A 0.0274(17) 0.0209(17) 0.081(3) 0.0283(17) 0.0136(18) 0.0095(15) O1A 0.0332(13) 0.0313(13) 0.128(2) 0.0386(14) 0.0484(15) 0.0225(11) O2B 0.0697(19) 0.0402(15) 0.0646(18) 0.0030(13) 0.0385(15) -0.0251(14) O3B 0.186(4) 0.0386(18) 0.195(4) -0.016(2) 0.166(4) -0.018(2) N1A 0.0211(13) 0.0196(13) 0.078(2) 0.0219(13) 0.0224(14) 0.0116(11) N2B 0.085(3) 0.0305(18) 0.094(3) -0.0016(18) 0.063(2) -0.0172(18) C2B 0.0199(15) 0.0221(16) 0.056(2) 0.0162(14) 0.0157(14) 0.0079(13) C3B 0.040(2) 0.0248(18) 0.067(3) 0.0102(17) 0.0272(19) -0.0059(16) C4B 0.053(2) 0.042(2) 0.057(3) 0.010(2) 0.027(2) -0.0135(19) C5B 0.0304(19) 0.039(2) 0.055(2) 0.0251(18) 0.0094(17) -0.0053(16) C6B 0.0213(16) 0.0256(18) 0.056(2) 0.0234(17) 0.0069(15) 0.0048(14) _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 O1B N1B 1.299(3) . ? O3A N2A 1.229(4) . ? O2A N2A 1.228(4) . ? N1B C6B 1.364(4) . ? N1B C2B 1.372(4) . ? N2A C3A 1.476(4) . ? C2A N1A 1.370(4) . ? C2A C3A 1.386(4) . ? C2A C2B 1.479(4) . ? C3A C4A 1.371(4) . ? C4A C5A 1.376(4) . ? C5A C6A 1.365(4) . ? C6A N1A 1.364(4) . ? O1A N1A 1.304(3) . ? O2B N2B 1.230(4) . ? O3B N2B 1.214(4) . ? N2B C3B 1.477(5) . ? C2B C3B 1.392(5) . ? C3B C4B 1.373(5) . ? C4B C5B 1.390(5) . ? C5B C6B 1.359(5) . ? 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 O1B N1B C6B 120.0(2) . . ? O1B N1B C2B 119.9(2) . . ? C6B N1B C2B 120.1(3) . . ? O3A N2A O2A 124.9(3) . . ? O2A N2A C3A 118.5(3) . . ? O3A N2A C3A 116.6(3) . . ? N1A C2A C3A 117.9(3) . . ? N1A C2A C2B 115.4(2) . . ? C3A C2A C2B 126.7(2) . . ? C4A C3A C2A 122.9(3) . . ? C4A C3A N2A 118.3(3) . . ? C2A C3A N2A 118.7(3) . . ? C3A C4A C5A 117.2(3) . . ? C6A C5A C4A 120.8(3) . . ? N1A C6A C5A 121.0(3) . . ? O1A N1A C6A 120.2(2) . . ? O1A N1A C2A 119.7(2) . . ? C6A N1A C2A 120.1(2) . . ? O3B N2B O2B 125.1(3) . . ? O3B N2B C3B 117.2(3) . . ? O2B N2B C3B 117.6(3) . . ? N1B C2B C3B 117.7(3) . . ? N1B C2B C2A 117.0(3) . . ? C3B C2B C2A 125.2(3) . . ? C4B C3B C2B 123.1(3) . . ? C4B C3B N2B 117.3(3) . . ? C2B C3B N2B 119.5(3) . . ? C3B C4B C5B 116.8(4) . . ? C6B C5B C4B 120.8(3) . . ? C5B C6B N1B 121.4(3) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.472 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.065 data_compound15 _database_code_depnum_ccdc_archive 'CCDC 648400' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5,5'-dimethyl-2,2'-bipyridine-1-oxide ; _chemical_name_common 5,5'-dimethyl-2,2'-bipyridine-1-oxide _chemical_melting_point 484-487 _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 N4 O5' _chemical_formula_weight 290.24 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 monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 8.1670(3) _cell_length_b 13.4699(6) _cell_length_c 11.3597(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.7505(16) _cell_angle_gamma 90.00 _cell_volume 1245.37(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5802 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.866 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) See R.H. Blessing, Acta Cryst., (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relecvant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9531 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2826 _reflns_number_gt 1949 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_cell_refinement ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_data_reduction ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; There is a small degree of disorder in which pyridine N atom carries the O atom: 92:8. The two N-O bonds were restrained to be similar. 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^)+(0.1002P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2826 _refine_ls_number_parameters 214 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1478 _refine_ls_wR_factor_gt 0.1352 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_restrained_S_all 0.945 _refine_ls_shift/su_max 0.035 _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 O1A O 0.1701(2) -0.07478(11) 0.42576(15) 0.0378(6) Uani 0.915(4) 1 d PD . . O2A O 0.08437(17) 0.21841(11) 0.15771(12) 0.0317(4) Uani 1 1 d . . . O3A O 0.02001(16) 0.32540(11) 0.28915(13) 0.0309(4) Uani 1 1 d . . . N1A N 0.1934(2) 0.01925(12) 0.42965(14) 0.0265(4) Uani 1 1 d D . . N2A N 0.07678(17) 0.24616(13) 0.26019(14) 0.0218(4) Uani 1 1 d . . . C2A C 0.1228(2) 0.07865(15) 0.34304(16) 0.0214(4) Uani 1 1 d . . . C3A C 0.1454(2) 0.17957(14) 0.35509(16) 0.0199(4) Uani 1 1 d . . . C4A C 0.2369(2) 0.22256(16) 0.44921(17) 0.0223(4) Uani 1 1 d . . . C5A C 0.3131(2) 0.15962(15) 0.53423(16) 0.0248(5) Uani 1 1 d . . . C6A C 0.2887(2) 0.05928(16) 0.52163(18) 0.0272(5) Uani 1 1 d . . . C7A C 0.4217(3) 0.19858(17) 0.63730(19) 0.0349(5) Uani 1 1 d . . . H7A1 H 0.3633 0.1947 0.7091 0.052 Uiso 1 1 calc R . . H7A2 H 0.4504 0.2679 0.6225 0.052 Uiso 1 1 calc R . . H7A3 H 0.5221 0.1586 0.6474 0.052 Uiso 1 1 calc R . . O1B O -0.190(2) 0.1231(11) 0.3135(13) 0.043(6) Uiso 0.085(4) 1 d PD . . O2B O 0.33722(15) -0.01956(11) 0.21220(13) 0.0319(4) Uani 1 1 d . . . O3B O 0.26067(17) -0.16413(12) 0.14712(14) 0.0398(4) Uani 1 1 d . . . N1B N -0.14259(19) 0.06152(13) 0.24082(15) 0.0275(4) Uani 1 1 d D . . N2B N 0.23118(18) -0.08027(13) 0.18045(14) 0.0250(4) Uani 1 1 d . . . C2B C 0.0131(2) 0.02903(14) 0.24959(16) 0.0216(4) Uani 1 1 d . . . C3B C 0.0583(2) -0.04938(14) 0.17968(16) 0.0212(4) Uani 1 1 d . . . C4B C -0.0564(2) -0.09953(16) 0.10548(17) 0.0231(4) Uani 1 1 d . . . C5B C -0.2189(2) -0.06781(15) 0.09876(16) 0.0235(4) Uani 1 1 d . . . C6B C -0.2534(2) 0.01423(16) 0.16610(18) 0.0272(5) Uani 1 1 d . . . C7B C -0.3514(2) -0.12101(16) 0.02373(18) 0.0278(5) Uani 1 1 d . . . H7B1 H -0.4568 -0.0875 0.0303 0.042 Uiso 1 1 calc R . . H7B2 H -0.3589 -0.1898 0.0508 0.042 Uiso 1 1 calc R . . H7B3 H -0.3249 -0.1204 -0.0589 0.042 Uiso 1 1 calc R . . H4A H 0.252(2) 0.2885(15) 0.4555(16) 0.012(5) Uiso 1 1 d . . . H6A H 0.338(3) 0.0079(17) 0.575(2) 0.033(6) Uiso 1 1 d . . . H4B H -0.026(2) -0.1492(17) 0.0634(19) 0.024(5) Uiso 1 1 d . . . H6B H -0.366(3) 0.0405(15) 0.1624(18) 0.026(5) 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 O1A 0.0595(11) 0.0170(9) 0.0339(10) 0.0048(7) -0.0142(8) -0.0030(7) O2A 0.0406(8) 0.0355(9) 0.0183(8) 0.0009(6) -0.0022(6) 0.0076(6) O3A 0.0323(8) 0.0250(8) 0.0355(9) 0.0017(6) 0.0040(6) 0.0077(6) N1A 0.0343(9) 0.0209(10) 0.0229(9) 0.0034(7) -0.0065(7) -0.0043(7) N2A 0.0192(7) 0.0232(9) 0.0226(9) 0.0012(7) -0.0006(6) 0.0000(7) C2A 0.0199(9) 0.0260(11) 0.0176(9) 0.0014(8) -0.0025(7) -0.0004(8) C3A 0.0180(8) 0.0236(11) 0.0180(9) 0.0017(7) 0.0007(7) 0.0012(7) C4A 0.0232(9) 0.0204(11) 0.0232(10) -0.0020(8) 0.0013(7) -0.0023(8) C5A 0.0253(9) 0.0307(12) 0.0181(10) -0.0014(8) -0.0001(7) -0.0005(8) C6A 0.0316(10) 0.0280(12) 0.0206(10) 0.0046(9) -0.0059(8) 0.0003(9) C7A 0.0410(12) 0.0387(14) 0.0230(11) -0.0016(9) -0.0094(9) -0.0043(10) O2B 0.0220(7) 0.0298(9) 0.0427(9) 0.0003(6) -0.0046(6) -0.0047(6) O3B 0.0301(8) 0.0337(9) 0.0544(11) -0.0175(8) -0.0030(7) 0.0054(6) N1B 0.0231(8) 0.0343(11) 0.0242(9) -0.0011(7) -0.0027(6) 0.0002(7) N2B 0.0223(8) 0.0268(10) 0.0251(9) -0.0011(7) -0.0032(6) 0.0008(7) C2B 0.0229(9) 0.0224(11) 0.0190(10) 0.0028(8) -0.0015(7) -0.0034(8) C3B 0.0201(9) 0.0233(10) 0.0197(10) 0.0038(8) -0.0019(7) -0.0007(7) C4B 0.0255(10) 0.0226(11) 0.0206(10) -0.0001(8) -0.0010(7) -0.0012(8) C5B 0.0251(9) 0.0273(11) 0.0174(10) 0.0055(8) -0.0024(7) -0.0043(8) C6B 0.0211(10) 0.0327(12) 0.0271(11) -0.0013(9) -0.0019(7) -0.0013(8) C7B 0.0263(9) 0.0308(12) 0.0250(11) 0.0029(9) -0.0066(8) -0.0059(8) _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 O1A N1A 1.281(2) . ? O2A N2A 1.229(2) . ? O3A N2A 1.220(2) . ? N1A C2A 1.359(2) . ? N1A C6A 1.362(3) . ? N2A C3A 1.477(2) . ? C2A C3A 1.377(3) . ? C2A C2B 1.490(3) . ? C3A C4A 1.380(3) . ? C4A C5A 1.393(3) . ? C5A C6A 1.372(3) . ? C5A C7A 1.503(3) . ? O1B N1B 1.253(7) . ? O2B N2B 1.223(2) . ? O3B N2B 1.222(2) . ? N1B C2B 1.341(2) . ? N1B C6B 1.348(2) . ? N2B C3B 1.471(2) . ? C2B C3B 1.390(3) . ? C3B C4B 1.383(3) . ? C4B C5B 1.390(3) . ? C5B C6B 1.386(3) . ? C5B C7B 1.503(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 O1A N1A C2A 120.30(16) . . ? O1A N1A C6A 119.46(16) . . ? C2A N1A C6A 120.25(17) . . ? O3A N2A O2A 124.86(16) . . ? O3A N2A C3A 117.68(15) . . ? O2A N2A C3A 117.44(16) . . ? N1A C2A C3A 117.65(17) . . ? N1A C2A C2B 116.47(17) . . ? C3A C2A C2B 125.56(16) . . ? C2A C3A C4A 123.42(17) . . ? C2A C3A N2A 119.17(16) . . ? C4A C3A N2A 117.33(17) . . ? C3A C4A C5A 117.65(19) . . ? C6A C5A C4A 118.34(18) . . ? C6A C5A C7A 119.75(18) . . ? C4A C5A C7A 121.90(19) . . ? N1A C6A C5A 122.61(18) . . ? O1B N1B C2B 120.5(8) . . ? O1B N1B C6B 120.1(8) . . ? C2B N1B C6B 118.39(17) . . ? O3B N2B O2B 123.81(15) . . ? O3B N2B C3B 118.25(15) . . ? O2B N2B C3B 117.92(16) . . ? N1B C2B C3B 120.06(17) . . ? N1B C2B C2A 114.65(16) . . ? C3B C2B C2A 125.16(16) . . ? C4B C3B C2B 121.39(16) . . ? C4B C3B N2B 117.81(17) . . ? C2B C3B N2B 120.78(15) . . ? C3B C4B C5B 118.59(19) . . ? C6B C5B C4B 116.84(17) . . ? C6B C5B C7B 121.54(17) . . ? C4B C5B C7B 121.60(18) . . ? N1B C6B C5B 124.57(17) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.381 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.061 data_compound16 _database_code_depnum_ccdc_archive 'CCDC 648401' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5,5-Dimethyl-3,3-dinitro-2,2-bipyridine-1,1-dioxide ; _chemical_name_common 5,5-Dimethyl-3,3-dinitro-2,2-bipyridine-1,1-dioxide _chemical_melting_point 484 _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 N4 O6' _chemical_formula_weight 306.24 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 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 12.044(4) _cell_length_b 7.544(3) _cell_length_c 15.093(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.480(3) _cell_angle_gamma 90.00 _cell_volume 1300.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5599 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.780 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) See R.H. Blessing, Acta Cryst., (1995), A51, 33-38 ; _exptl_special_details ? _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6827 _diffrn_reflns_av_R_equivalents 0.0592 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1462 _reflns_number_gt 1272 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_cell_refinement ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_data_reduction ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0628P)^2^+3.1650P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1462 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1537 _refine_ls_wR_factor_gt 0.1499 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.002 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 O1A O 0.04758(12) 0.0976(2) 0.62248(11) 0.0264(4) Uani 1 1 d . . . O2A O -0.08876(13) -0.2845(2) 0.84069(12) 0.0333(5) Uani 1 1 d . . . O3A O -0.26372(14) -0.1776(2) 0.81131(12) 0.0332(4) Uani 1 1 d . . . N1A N -0.04995(14) 0.0313(2) 0.62782(12) 0.0197(4) Uani 1 1 d . . . N2A N -0.17163(15) -0.1956(2) 0.79451(13) 0.0244(4) Uani 1 1 d . . . C2A C -0.05463(16) -0.0412(3) 0.70990(14) 0.0196(5) Uani 1 1 d . . . C3A C -0.16225(17) -0.1085(3) 0.71005(15) 0.0208(5) Uani 1 1 d . . . C4A C -0.26190(17) -0.1042(3) 0.63352(15) 0.0219(5) Uani 1 1 d . . . C5A C -0.25362(17) -0.0306(3) 0.55073(15) 0.0207(5) Uani 1 1 d . . . C6A C -0.14710(18) 0.0334(3) 0.55020(15) 0.0215(5) Uani 1 1 d . . . C7A C -0.35920(18) -0.0233(3) 0.46493(15) 0.0261(5) Uani 1 1 d . . . H71 H -0.4058 0.0818 0.4677 0.039 Uiso 1 1 calc R . . H72 H -0.4067 -0.1300 0.4618 0.039 Uiso 1 1 calc R . . H73 H -0.3340 -0.0169 0.4093 0.039 Uiso 1 1 calc R . . H4A H -0.336(2) -0.161(4) 0.6378(18) 0.027(6) Uiso 1 1 d . . . H6A H -0.132(2) 0.078(4) 0.4998(19) 0.026(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 O1A 0.0201(7) 0.0328(9) 0.0285(8) 0.0002(7) 0.0109(6) -0.0081(6) O2A 0.0250(8) 0.0327(9) 0.0383(10) 0.0154(7) 0.0047(7) -0.0008(7) O3A 0.0271(8) 0.0426(10) 0.0350(9) 0.0066(8) 0.0171(7) -0.0005(7) N1A 0.0180(8) 0.0215(9) 0.0213(9) -0.0010(7) 0.0085(7) -0.0023(6) N2A 0.0211(8) 0.0256(9) 0.0270(10) 0.0031(7) 0.0083(7) -0.0038(7) C2A 0.0179(10) 0.0191(10) 0.0228(10) -0.0008(7) 0.0081(8) 0.0007(7) C3A 0.0210(9) 0.0174(10) 0.0258(11) 0.0012(8) 0.0102(8) 0.0012(8) C4A 0.0180(9) 0.0191(10) 0.0297(11) -0.0020(8) 0.0094(8) -0.0002(8) C5A 0.0191(10) 0.0186(10) 0.0243(11) -0.0049(8) 0.0068(8) 0.0005(8) C6A 0.0228(10) 0.0225(10) 0.0199(10) -0.0007(8) 0.0080(8) -0.0003(8) C7A 0.0211(10) 0.0309(12) 0.0239(11) -0.0021(9) 0.0038(8) -0.0014(9) _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 O1A N1A 1.302(2) . ? O2A N2A 1.221(2) . ? O3A N2A 1.221(2) . ? N1A C6A 1.369(3) . ? N1A C2A 1.372(3) . ? N2A C3A 1.470(3) . ? C2A C3A 1.393(3) . ? C2A C2A 1.479(4) 6_557 ? C3A C4A 1.377(3) . ? C4A C5A 1.399(3) . ? C5A C6A 1.373(3) . ? C5A C7A 1.501(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 O1A N1A C6A 119.06(17) . . ? O1A N1A C2A 120.34(16) . . ? C6A N1A C2A 120.60(17) . . ? O2A N2A O3A 125.06(19) . . ? O2A N2A C3A 117.83(17) . . ? O3A N2A C3A 117.06(17) . . ? N1A C2A C3A 116.85(18) . . ? N1A C2A C2A 117.3(2) . 6_557 ? C3A C2A C2A 125.9(2) . 6_557 ? C4A C3A C2A 123.6(2) . . ? C4A C3A N2A 116.87(18) . . ? C2A C3A N2A 119.45(18) . . ? C3A C4A C5A 117.94(18) . . ? C6A C5A C4A 118.41(19) . . ? C6A C5A C7A 121.30(19) . . ? C4A C5A C7A 120.28(19) . . ? N1A C6A C5A 122.5(2) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.445 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.069 data_compound22 _database_code_depnum_ccdc_archive 'CCDC 648402' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 8-nitroquinoline-1-oxide ; _chemical_name_common 8-nitroquinoline-1-oxide _chemical_melting_point 451-452 _chemical_formula_moiety ? _chemical_formula_sum 'C9 H6 N2 O3' _chemical_formula_weight 190.16 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.8557(6) _cell_length_b 8.8130(6) _cell_length_c 11.4793(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.780(4) _cell_angle_gamma 90.00 _cell_volume 793.01(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1810 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description slab _exptl_crystal_colour orange _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.77 _exptl_absorpt_correction_T_max 0.99 _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 95mm CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8940 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 27.51 _reflns_number_total 1809 _reflns_number_gt 1465 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _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^)+(0.0564P)^2^+0.2631P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1809 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.1067 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 0.19743(15) 0.06546(13) 0.10487(10) 0.0224(3) Uani 1 1 d . . . O1 O 0.19433(14) 0.18531(12) 0.17087(10) 0.0316(3) Uani 1 1 d . . . C7 C 0.42417(18) 0.21885(17) -0.14201(13) 0.0245(3) Uani 1 1 d . . . N2 N 0.32942(16) 0.35577(13) 0.02402(11) 0.0260(3) Uani 1 1 d . . . O3 O 0.45314(14) 0.39275(13) 0.08876(9) 0.0316(3) Uani 1 1 d . . . C10 C 0.28222(18) -0.05649(15) -0.07175(12) 0.0212(3) Uani 1 1 d . . . C9 C 0.27119(17) 0.07510(15) -0.00190(12) 0.0201(3) Uani 1 1 d . . . O2 O 0.20265(15) 0.43317(12) 0.00243(12) 0.0387(3) Uani 1 1 d . . . C8 C 0.34136(18) 0.21170(15) -0.04093(13) 0.0218(3) Uani 1 1 d . . . C2 C 0.13510(19) -0.06767(16) 0.13992(14) 0.0254(3) Uani 1 1 d . . . C4 C 0.21338(19) -0.19457(16) -0.03294(14) 0.0250(3) Uani 1 1 d . . . C3 C 0.14116(19) -0.19832(16) 0.07168(14) 0.0258(3) Uani 1 1 d . . . C6 C 0.43723(19) 0.08736(17) -0.21045(13) 0.0256(3) Uani 1 1 d . . . C5 C 0.36659(19) -0.04569(17) -0.17692(13) 0.0241(3) Uani 1 1 d . . . H5 H 0.373(2) -0.135(2) -0.2223(16) 0.033(5) Uiso 1 1 d . . . H6 H 0.501(2) 0.0952(19) -0.2833(16) 0.030(4) Uiso 1 1 d . . . H7 H 0.476(2) 0.314(2) -0.1623(15) 0.028(4) Uiso 1 1 d . . . H4 H 0.221(2) -0.286(2) -0.0797(15) 0.030(4) Uiso 1 1 d . . . H3 H 0.095(2) -0.291(2) 0.1000(16) 0.035(5) Uiso 1 1 d . . . H2 H 0.090(2) -0.0682(18) 0.2172(15) 0.026(4) 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 N1 0.0242(6) 0.0180(6) 0.0256(7) -0.0016(5) 0.0054(5) 0.0008(5) O1 0.0421(7) 0.0216(5) 0.0325(6) -0.0076(4) 0.0130(5) -0.0015(5) C7 0.0251(7) 0.0216(7) 0.0269(8) 0.0044(6) 0.0019(6) -0.0001(6) N2 0.0319(7) 0.0157(6) 0.0310(7) 0.0010(5) 0.0065(5) -0.0020(5) O3 0.0371(6) 0.0275(6) 0.0306(6) -0.0066(4) 0.0050(5) -0.0074(5) C10 0.0205(7) 0.0179(7) 0.0249(7) -0.0007(5) -0.0008(5) 0.0018(5) C9 0.0202(7) 0.0179(7) 0.0223(7) 0.0015(5) 0.0012(5) 0.0012(5) O2 0.0394(7) 0.0198(6) 0.0571(8) -0.0013(5) 0.0049(6) 0.0081(5) C8 0.0235(7) 0.0156(7) 0.0262(7) -0.0009(5) -0.0001(5) 0.0012(5) C2 0.0256(7) 0.0239(7) 0.0274(8) 0.0034(6) 0.0065(6) -0.0008(6) C4 0.0261(7) 0.0180(7) 0.0307(8) -0.0014(6) -0.0006(6) -0.0006(6) C3 0.0251(7) 0.0186(7) 0.0339(8) 0.0036(6) 0.0020(6) -0.0021(6) C6 0.0264(7) 0.0280(7) 0.0224(7) 0.0017(6) 0.0024(6) 0.0030(6) C5 0.0257(7) 0.0236(7) 0.0227(7) -0.0027(6) 0.0006(6) 0.0024(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 N1 O1 1.3010(15) . ? N1 C2 1.3432(18) . ? N1 C9 1.3924(18) . ? C7 C8 1.369(2) . ? C7 C6 1.408(2) . ? N2 O2 1.2190(17) . ? N2 O3 1.2280(16) . ? N2 C8 1.4785(17) . ? C10 C4 1.415(2) . ? C10 C9 1.4158(19) . ? C10 C5 1.418(2) . ? C9 C8 1.4094(19) . ? C2 C3 1.395(2) . ? C4 C3 1.362(2) . ? C6 C5 1.363(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 O1 N1 C2 120.89(12) . . ? O1 N1 C9 119.21(11) . . ? C2 N1 C9 119.87(12) . . ? C8 C7 C6 119.44(13) . . ? O2 N2 O3 125.31(13) . . ? O2 N2 C8 117.14(12) . . ? O3 N2 C8 117.33(12) . . ? C4 C10 C9 119.14(13) . . ? C4 C10 C5 122.36(13) . . ? C9 C10 C5 118.47(12) . . ? N1 C9 C8 121.75(12) . . ? N1 C9 C10 119.54(12) . . ? C8 C9 C10 118.67(13) . . ? C7 C8 C9 121.78(13) . . ? C7 C8 N2 115.95(12) . . ? C9 C8 N2 122.28(12) . . ? N1 C2 C3 121.74(14) . . ? C3 C4 C10 119.24(13) . . ? C4 C3 C2 120.44(13) . . ? C5 C6 C7 120.30(14) . . ? C6 C5 C10 121.31(13) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.239 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.054