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_contact_author_name 'Prof C. Wilson' _publ_contact_author_address ; Department of Chemistry University of Glasgow Glasgow G12 8QQ UNITED KINGDOM ; _publ_contact_author_email CHICK@CHEM.GLA.AC.UK _publ_section_title ; Towards Proton Transfer in Hydrogen Bonded Molecular Complexes: Joint Experimental and Theoretical Modelling and an Energy Scale for Polymorphism ; loop_ _publ_author_name C.Wilson 'Matthias J. Gutmann' 'Derek Middlemiss' 'Marc Schmidtmann' # Attachment 'IN-OA_Form_I.cif' data_hain _database_code_depnum_ccdc_archive 'CCDC 643946' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 N4 O6' _chemical_formula_weight 334.29 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 11.6911(12) _cell_length_b 9.9945(10) _cell_length_c 12.1366(12) _cell_angle_alpha 90.00 _cell_angle_beta 102.743(5) _cell_angle_gamma 90.00 _cell_volume 1383.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6224 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 33.95 _exptl_crystal_description block/plate _exptl_crystal_colour colorless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10080 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 33.97 _reflns_number_total 2782 _reflns_number_gt 2541 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.4000P] 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 2782 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 O1 O 0.03766(6) 0.69269(5) 0.65610(5) 0.01817(13) Uani 1 1 d . . . H1 H 0.0702(12) 0.6965(14) 0.5696(11) 0.027 Uiso 1 1 d . . . O2 O 0.03862(5) 0.91687(5) 0.65053(4) 0.01576(12) Uani 1 1 d . . . O3 O 0.24221(5) 0.63579(5) 0.11434(4) 0.01821(13) Uani 1 1 d . . . N1 N 0.09980(5) 0.70119(6) 0.46765(5) 0.01273(12) Uani 1 1 d . . . N2 N 0.17231(6) 0.84781(6) 0.09236(5) 0.01396(12) Uani 1 1 d . . . C1 C 0.02189(6) 0.81062(7) 0.69427(5) 0.01222(13) Uani 1 1 d . . . C2 C 0.11357(6) 0.59118(6) 0.40853(6) 0.01368(13) Uani 1 1 d . . . H2 H 0.1024(11) 0.5062(13) 0.4403(10) 0.023(3) Uiso 1 1 d . . . C3 C 0.14390(6) 0.59928(6) 0.30467(5) 0.01307(13) Uani 1 1 d . . . H3 H 0.1510(11) 0.5163(15) 0.2610(11) 0.032(3) Uiso 1 1 d . . . C4 C 0.16081(6) 0.72500(6) 0.26121(5) 0.01088(12) Uani 1 1 d . . . C5 C 0.14666(6) 0.83853(7) 0.32325(6) 0.01256(13) Uani 1 1 d . . . H4 H 0.1587(11) 0.9315(13) 0.3004(10) 0.025(3) Uiso 1 1 d . . . C6 C 0.11572(6) 0.82208(7) 0.42605(6) 0.01288(13) Uani 1 1 d . . . H5 H 0.1011(11) 0.8963(12) 0.4733(10) 0.020(3) Uiso 1 1 d . . . C7 C 0.19487(6) 0.73316(6) 0.14917(5) 0.01180(13) Uani 1 1 d . . . H6 H 0.1919(11) 0.8533(12) 0.0229(11) 0.023(3) Uiso 1 1 d . . . H7 H 0.1327(13) 0.9144(14) 0.1164(11) 0.029(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0331(3) 0.0098(2) 0.0157(2) -0.00055(16) 0.0143(2) 0.00090(18) O2 0.0240(3) 0.0107(2) 0.0145(2) 0.00114(15) 0.00851(19) -0.00189(16) O3 0.0297(3) 0.0134(2) 0.0152(2) 0.00183(17) 0.0128(2) 0.00716(19) N1 0.0162(3) 0.0122(2) 0.0110(2) 0.00053(18) 0.00560(19) 0.00134(18) N2 0.0208(3) 0.0110(2) 0.0121(2) 0.00177(18) 0.0079(2) 0.00280(19) C1 0.0161(3) 0.0104(3) 0.0111(3) 0.00031(18) 0.0050(2) -0.00015(19) C2 0.0195(3) 0.0107(3) 0.0125(3) 0.00106(19) 0.0073(2) 0.0007(2) C3 0.0189(3) 0.0100(3) 0.0118(3) -0.00011(19) 0.0066(2) 0.0011(2) C4 0.0136(3) 0.0107(2) 0.0093(2) -0.00002(18) 0.00455(19) 0.00085(19) C5 0.0174(3) 0.0103(2) 0.0113(2) -0.00018(19) 0.0060(2) 0.0000(2) C6 0.0176(3) 0.0114(3) 0.0108(3) -0.00086(19) 0.0056(2) 0.0007(2) C7 0.0153(3) 0.0108(3) 0.0104(2) 0.00005(19) 0.0052(2) 0.0010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2944(8) . ? O1 H1 1.194(13) . ? O2 C1 1.2221(8) . ? O3 C7 1.2390(8) . ? N1 C6 1.3382(8) . ? N1 C2 1.3418(8) . ? N1 H1 1.357(13) . ? N2 C7 1.3333(8) . ? N2 H6 0.922(13) . ? N2 H7 0.895(14) . ? C1 C1 1.5482(13) 2_556 ? C2 C3 1.3851(9) . ? C2 H2 0.953(13) . ? C3 C4 1.3936(9) . ? C3 H3 0.998(14) . ? C4 C5 1.3916(9) . ? C4 C7 1.5011(9) . ? C5 C6 1.3834(9) . ? C5 H4 0.989(13) . ? C6 H5 0.976(12) . ? 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 C1 O1 H1 112.6(7) . . ? C6 N1 C2 119.67(6) . . ? C6 N1 H1 117.4(6) . . ? C2 N1 H1 122.9(6) . . ? C7 N2 H6 117.6(8) . . ? C7 N2 H7 121.9(9) . . ? H6 N2 H7 120.2(12) . . ? O2 C1 O1 125.92(6) . . ? O2 C1 C1 119.67(4) . 2_556 ? O1 C1 C1 114.42(4) . 2_556 ? N1 C2 C3 121.58(6) . . ? N1 C2 H2 118.0(7) . . ? C3 C2 H2 120.4(7) . . ? C2 C3 C4 118.90(6) . . ? C2 C3 H3 120.2(8) . . ? C4 C3 H3 120.9(8) . . ? C5 C4 C3 119.12(6) . . ? C5 C4 C7 122.19(6) . . ? C3 C4 C7 118.68(5) . . ? C6 C5 C4 118.48(6) . . ? C6 C5 H4 116.5(7) . . ? C4 C5 H4 125.0(7) . . ? N1 C6 C5 122.24(6) . . ? N1 C6 H5 114.1(7) . . ? C5 C6 H5 123.7(7) . . ? O3 C7 N2 123.43(6) . . ? O3 C7 C4 119.61(6) . . ? N2 C7 C4 116.96(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 1.194(13) 1.357(13) 2.5493(8) 176.3(12) . _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 33.97 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.593 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.063 # Attachment 'IN-OA_Form_II.cif' data_oxaiso6 _database_code_depnum_ccdc_archive 'CCDC 643947' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 N4 O6' _chemical_formula_weight 334.29 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 3.6811(7) _cell_length_b 7.5912(14) _cell_length_c 12.455(2) _cell_angle_alpha 85.638(9) _cell_angle_beta 87.856(10) _cell_angle_gamma 84.221(10) _cell_volume 345.11(11) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3240 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 33.81 _exptl_crystal_description stick _exptl_crystal_colour colorless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 174 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8148 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 33.92 _reflns_number_total 2759 _reflns_number_gt 2340 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0400P] 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 2759 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1212 _refine_ls_wR_factor_gt 0.1153 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 O1 O 1.29804(19) 1.80006(8) 0.52094(5) 0.01610(15) Uani 1 1 d . . . H1 H 1.209(4) 1.7154(19) 0.6011(11) 0.024 Uiso 1 1 d . . . O2 O 1.50442(19) 1.96801(8) 0.64052(5) 0.01596(14) Uani 1 1 d . . . O3 O 0.6933(2) 1.22319(9) 0.99567(5) 0.01671(15) Uani 1 1 d . . . N1 N 1.09828(19) 1.59195(9) 0.67528(6) 0.01248(14) Uani 1 1 d . . . N2 N 0.5882(2) 1.05275(9) 0.86038(6) 0.01344(15) Uani 1 1 d . . . C1 C 1.4465(2) 1.93596(10) 0.54826(6) 0.01136(15) Uani 1 1 d . . . C2 C 1.0714(2) 1.42874(11) 0.64463(6) 0.01247(15) Uani 1 1 d . . . H2 H 1.162(4) 1.4025(18) 0.5720(10) 0.016(3) Uiso 1 1 d . . . C3 C 0.9358(2) 1.29713(10) 0.71308(6) 0.01177(15) Uani 1 1 d . . . H3 H 0.924(4) 1.1804(19) 0.6844(11) 0.022(3) Uiso 1 1 d . . . C4 C 0.8316(2) 1.33598(10) 0.81781(6) 0.01015(14) Uani 1 1 d . . . C5 C 0.8648(2) 1.50563(10) 0.84967(6) 0.01218(15) Uani 1 1 d . . . H4 H 0.787(4) 1.5434(18) 0.9202(10) 0.019(3) Uiso 1 1 d . . . C6 C 0.9973(2) 1.63129(10) 0.77588(7) 0.01310(16) Uani 1 1 d . . . H5 H 1.018(4) 1.7513(19) 0.7940(11) 0.025(3) Uiso 1 1 d . . . C7 C 0.6964(2) 1.19813(10) 0.89893(6) 0.01108(15) Uani 1 1 d . . . H6 H 0.497(4) 0.961(2) 0.9101(12) 0.030(4) Uiso 1 1 d . . . H7 H 0.573(4) 1.0370(18) 0.7877(11) 0.021(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0257(3) 0.0132(3) 0.0111(3) -0.0010(2) 0.0007(2) -0.0107(2) O2 0.0247(3) 0.0156(3) 0.0086(3) -0.0011(2) -0.0010(2) -0.0067(2) O3 0.0261(3) 0.0161(3) 0.0089(3) -0.0008(2) 0.0012(2) -0.0074(2) N1 0.0144(3) 0.0113(3) 0.0120(3) 0.0005(2) -0.0006(2) -0.0034(2) N2 0.0201(3) 0.0116(3) 0.0093(3) 0.0000(2) -0.0005(2) -0.0055(2) C1 0.0136(3) 0.0106(3) 0.0101(3) -0.0008(2) 0.0007(2) -0.0027(2) C2 0.0152(3) 0.0125(3) 0.0101(3) -0.0002(2) 0.0004(3) -0.0036(3) C3 0.0151(3) 0.0104(3) 0.0100(3) -0.0008(2) 0.0005(3) -0.0026(2) C4 0.0113(3) 0.0099(3) 0.0092(3) 0.0002(2) -0.0004(2) -0.0015(2) C5 0.0152(3) 0.0110(3) 0.0105(3) -0.0014(2) 0.0004(3) -0.0022(3) C6 0.0167(3) 0.0100(3) 0.0129(3) -0.0011(2) -0.0004(3) -0.0026(3) C7 0.0130(3) 0.0103(3) 0.0100(3) 0.0001(2) 0.0001(2) -0.0018(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2883(10) . ? O1 H1 1.199(14) . ? O2 C1 1.2232(10) . ? O3 C7 1.2334(10) . ? N1 C2 1.3379(11) . ? N1 C6 1.3405(11) . ? N1 H1 1.347(14) . ? N2 C7 1.3381(11) . ? N2 H6 0.975(16) . ? N2 H7 0.926(14) . ? C1 C1 1.5523(15) 2_896 ? C2 C3 1.3831(11) . ? C2 H2 0.981(13) . ? C3 C4 1.3907(11) . ? C3 H3 0.985(14) . ? C4 C5 1.3943(11) . ? C4 C7 1.5066(11) . ? C5 C6 1.3855(11) . ? C5 H4 0.969(13) . ? C6 H5 0.966(15) . ? 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 C1 O1 H1 108.7(7) . . ? C2 N1 C6 119.91(7) . . ? C2 N1 H1 118.2(6) . . ? C6 N1 H1 121.8(6) . . ? C7 N2 H6 119.6(9) . . ? C7 N2 H7 124.1(9) . . ? H6 N2 H7 116.0(13) . . ? O2 C1 O1 125.57(7) . . ? O2 C1 C1 120.39(9) . 2_896 ? O1 C1 C1 114.04(8) . 2_896 ? N1 C2 C3 122.22(7) . . ? N1 C2 H2 117.6(8) . . ? C3 C2 H2 120.1(8) . . ? C2 C3 C4 118.44(7) . . ? C2 C3 H3 117.3(8) . . ? C4 C3 H3 124.2(8) . . ? C3 C4 C5 119.05(7) . . ? C3 C4 C7 121.86(7) . . ? C5 C4 C7 119.06(7) . . ? C6 C5 C4 119.12(7) . . ? C6 C5 H4 117.4(8) . . ? C4 C5 H4 123.4(8) . . ? N1 C6 C5 121.25(7) . . ? N1 C6 H5 117.0(8) . . ? C5 C6 H5 121.7(8) . . ? O3 C7 N2 123.71(7) . . ? O3 C7 C4 119.38(7) . . ? N2 C7 C4 116.91(7) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 1.199(14) 1.347(14) 2.5294(10) 166.8(13) . _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 33.92 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.614 _refine_diff_density_min -0.538 _refine_diff_density_rms 0.077