# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email adb@chem.sdu.dk _publ_contact_author_name 'Andrew Bond' loop_ _publ_author_name 'Sandor Beko' 'Martin Schmidt' 'Andrew Bond' data_2 _database_code_depnum_ccdc_archive 'CCDC 855812' #TrackingRef '- revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'Quinoline/fumaric acid (2:1)' _chemical_melting_point ? _chemical_formula_moiety '2(C9 H7 N), C4 H4 O4' _chemical_formula_sum 'C22 H18 N2 O4' _chemical_formula_weight 374.38 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.8288(2) _cell_length_b 10.6688(5) _cell_length_c 12.0072(6) _cell_angle_alpha 67.070(3) _cell_angle_beta 89.415(3) _cell_angle_gamma 87.226(3) _cell_volume 451.17(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3288 _cell_measurement_theta_min 3.27 _cell_measurement_theta_max 25.23 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.901 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 150(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 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7367 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 25.37 _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.941 _reflns_number_total 1561 _reflns_number_gt 1268 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0369P)^2^+0.0998P] 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 1561 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0807 _refine_ls_wR_factor_gt 0.0747 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.155 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.031 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 0.2589(3) 0.65214(9) 0.59738(8) 0.0330(3) Uani 1 1 d . . . H1 H 0.155(5) 0.682(2) 0.6597(19) 0.080(6) Uiso 1 1 d . . . O2 O 0.3141(3) 0.44988(10) 0.75125(9) 0.0506(3) Uani 1 1 d . . . N1 N -0.0101(3) 0.73795(10) 0.75829(9) 0.0253(3) Uani 1 1 d . . . C2 C -0.1502(3) 0.64764(13) 0.85473(12) 0.0279(3) Uani 1 1 d . . . H2A H -0.1680 0.5577 0.8581 0.033 Uiso 1 1 calc R . . C3 C -0.2750(3) 0.67615(13) 0.95301(11) 0.0282(3) Uani 1 1 d . . . H3A H -0.3724 0.6070 1.0211 0.034 Uiso 1 1 calc R . . C4 C -0.2537(3) 0.80459(14) 0.94875(12) 0.0283(3) Uani 1 1 d . . . H4A H -0.3365 0.8261 1.0144 0.034 Uiso 1 1 calc R . . C5 C -0.0753(3) 1.04231(13) 0.83450(13) 0.0303(3) Uani 1 1 d . . . H5A H -0.1582 1.0696 0.8969 0.036 Uiso 1 1 calc R . . C6 C 0.0734(4) 1.13441(14) 0.73490(13) 0.0342(4) Uani 1 1 d . . . H6A H 0.0956 1.2253 0.7284 0.041 Uiso 1 1 calc R . . C7 C 0.1952(4) 1.09577(13) 0.64097(12) 0.0321(3) Uani 1 1 d . . . H7A H 0.2971 1.1611 0.5714 0.039 Uiso 1 1 calc R . . C8 C 0.1680(3) 0.96587(13) 0.64919(11) 0.0280(3) Uani 1 1 d . . . H8A H 0.2519 0.9408 0.5856 0.034 Uiso 1 1 calc R . . C9 C 0.0147(3) 0.86772(12) 0.75235(11) 0.0229(3) Uani 1 1 d . . . C10 C -0.1082(3) 0.90664(13) 0.84642(11) 0.0242(3) Uani 1 1 d . . . C12 C 0.3491(4) 0.52199(13) 0.64544(12) 0.0281(3) Uani 1 1 d . . . C13 C 0.4984(3) 0.46608(13) 0.55882(11) 0.0265(3) Uani 1 1 d . . . H13A H 0.5978 0.3756 0.5905 0.032 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 O1 0.0470(6) 0.0273(5) 0.0272(5) -0.0140(4) 0.0072(4) 0.0033(4) O2 0.0912(10) 0.0326(6) 0.0264(6) -0.0108(5) 0.0164(6) 0.0031(6) N1 0.0250(6) 0.0274(6) 0.0257(6) -0.0128(5) 0.0015(5) 0.0003(5) C2 0.0270(7) 0.0276(7) 0.0295(7) -0.0115(6) 0.0014(6) -0.0022(6) C3 0.0249(7) 0.0328(7) 0.0252(7) -0.0092(6) 0.0035(6) -0.0034(6) C4 0.0213(7) 0.0407(8) 0.0273(7) -0.0183(6) 0.0012(5) 0.0019(6) C5 0.0255(7) 0.0345(8) 0.0375(8) -0.0217(7) -0.0036(6) 0.0046(6) C6 0.0316(8) 0.0276(7) 0.0440(9) -0.0150(7) -0.0069(7) 0.0023(6) C7 0.0293(8) 0.0294(7) 0.0310(8) -0.0045(6) -0.0025(6) -0.0016(6) C8 0.0260(8) 0.0323(8) 0.0240(7) -0.0096(6) -0.0016(5) 0.0018(6) C9 0.0198(7) 0.0262(7) 0.0245(7) -0.0123(6) -0.0039(5) 0.0033(5) C10 0.0174(7) 0.0310(7) 0.0273(7) -0.0152(6) -0.0043(5) 0.0034(5) C12 0.0334(8) 0.0266(7) 0.0263(8) -0.0125(6) 0.0044(6) -0.0032(6) C13 0.0303(8) 0.0239(7) 0.0276(6) -0.0127(5) 0.0030(6) -0.0004(5) _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 C12 1.3090(16) . ? O1 H1 0.99(2) . ? O2 C12 1.2120(16) . ? N1 C2 1.3134(16) . ? N1 C9 1.3662(16) . ? C2 C3 1.4027(18) . ? C2 H2A 0.9500 . ? C3 C4 1.3576(19) . ? C3 H3A 0.9500 . ? C4 C10 1.4170(18) . ? C4 H4A 0.9500 . ? C5 C6 1.3581(19) . ? C5 C10 1.4097(18) . ? C5 H5A 0.9500 . ? C6 C7 1.411(2) . ? C6 H6A 0.9500 . ? C7 C8 1.3595(18) . ? C7 H7A 0.9500 . ? C8 C9 1.4175(18) . ? C8 H8A 0.9500 . ? C9 C10 1.4162(18) . ? C12 C13 1.4841(18) . ? C13 C13 1.313(2) 2_666 ? C13 H13A 0.9500 . ? 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 C12 O1 H1 110.1(11) . . ? C2 N1 C9 118.46(11) . . ? N1 C2 C3 123.85(12) . . ? N1 C2 H2A 118.1 . . ? C3 C2 H2A 118.1 . . ? C4 C3 C2 118.63(12) . . ? C4 C3 H3A 120.7 . . ? C2 C3 H3A 120.7 . . ? C3 C4 C10 120.01(12) . . ? C3 C4 H4A 120.0 . . ? C10 C4 H4A 120.0 . . ? C6 C5 C10 120.77(13) . . ? C6 C5 H5A 119.6 . . ? C10 C5 H5A 119.6 . . ? C5 C6 C7 120.33(13) . . ? C5 C6 H6A 119.8 . . ? C7 C6 H6A 119.8 . . ? C8 C7 C6 120.60(13) . . ? C8 C7 H7A 119.7 . . ? C6 C7 H7A 119.7 . . ? C7 C8 C9 120.16(12) . . ? C7 C8 H8A 119.9 . . ? C9 C8 H8A 119.9 . . ? N1 C9 C10 121.79(11) . . ? N1 C9 C8 119.01(11) . . ? C10 C9 C8 119.20(11) . . ? C5 C10 C9 118.93(12) . . ? C5 C10 C4 123.81(12) . . ? C9 C10 C4 117.25(11) . . ? O2 C12 O1 124.33(12) . . ? O2 C12 C13 121.18(12) . . ? O1 C12 C13 114.49(11) . . ? C13 C13 C12 124.04(15) 2_666 . ? C13 C13 H13A 118.0 2_666 . ? C12 C13 H13A 118.0 . . ? 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 C9 N1 C2 C3 -0.38(19) . . . . ? N1 C2 C3 C4 0.6(2) . . . . ? C2 C3 C4 C10 0.09(19) . . . . ? C10 C5 C6 C7 0.5(2) . . . . ? C5 C6 C7 C8 -0.5(2) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? C2 N1 C9 C10 -0.46(18) . . . . ? C2 N1 C9 C8 179.49(11) . . . . ? C7 C8 C9 N1 179.88(11) . . . . ? C7 C8 C9 C10 -0.17(19) . . . . ? C6 C5 C10 C9 -0.37(19) . . . . ? C6 C5 C10 C4 178.65(12) . . . . ? N1 C9 C10 C5 -179.87(11) . . . . ? C8 C9 C10 C5 0.18(18) . . . . ? N1 C9 C10 C4 1.05(18) . . . . ? C8 C9 C10 C4 -178.90(11) . . . . ? C3 C4 C10 C5 -179.87(12) . . . . ? C3 C4 C10 C9 -0.84(18) . . . . ? O2 C12 C13 C13 170.82(17) . . . 2_666 ? O1 C12 C13 C13 -8.5(2) . . . 2_666 ? 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 0.99(2) 1.63(2) 2.6227(13) 177.1(18) . #============================================================================= data_3 _database_code_depnum_ccdc_archive 'CCDC 855813' #TrackingRef '- revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common '6-Methylquinoline/fumaric acid (2:1)' _chemical_melting_point ? _chemical_formula_moiety '2(C10 H9 N), C4 H4 O4' _chemical_formula_sum 'C24 H22 N2 O4' _chemical_formula_weight 402.44 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.8896(2) _cell_length_b 19.6117(13) _cell_length_c 13.0475(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.417(3) _cell_angle_gamma 90.00 _cell_volume 994.40(10) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6619 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 25.28 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.000 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 150(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 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 13073 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 25.38 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.38 _diffrn_measured_fraction_theta_full 0.978 _reflns_number_total 1794 _reflns_number_gt 1557 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0574P)^2^+0.8059P] 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 1794 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1355 _refine_ls_wR_factor_gt 0.1291 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.137 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.309 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.053 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 0.3357(4) 0.36730(7) 0.47518(11) 0.0309(4) Uani 1 1 d . . . H1 H 0.434(9) 0.3377(18) 0.419(3) 0.080(11) Uiso 1 1 d . . . O2 O 0.2467(4) 0.44123(7) 0.34605(11) 0.0321(4) Uani 1 1 d . . . N1 N 0.5722(4) 0.28661(8) 0.33581(13) 0.0246(4) Uani 1 1 d . . . C2 C 0.7175(5) 0.31245(11) 0.25533(16) 0.0272(5) Uani 1 1 d . . . H2A H 0.7560 0.3603 0.2533 0.033 Uiso 1 1 calc R . . C3 C 0.8182(5) 0.27276(11) 0.17243(16) 0.0288(5) Uani 1 1 d . . . H3A H 0.9216 0.2936 0.1157 0.035 Uiso 1 1 calc R . . C4 C 0.7662(5) 0.20394(11) 0.17402(15) 0.0267(5) Uani 1 1 d . . . H4A H 0.8362 0.1764 0.1188 0.032 Uiso 1 1 calc R . . C5 C 0.5360(5) 0.10341(10) 0.26623(16) 0.0247(5) Uani 1 1 d . . . H5A H 0.5990 0.0738 0.2126 0.030 Uiso 1 1 calc R . . C6 C 0.3776(5) 0.07688(10) 0.34936(16) 0.0250(5) Uani 1 1 d . . . C7 C 0.2900(5) 0.12176(11) 0.42933(16) 0.0268(5) Uani 1 1 d . . . H7A H 0.1824 0.1039 0.4876 0.032 Uiso 1 1 calc R . . C8 C 0.3564(5) 0.19004(10) 0.42483(15) 0.0251(5) Uani 1 1 d . . . H8A H 0.2955 0.2189 0.4796 0.030 Uiso 1 1 calc R . . C9 C 0.5148(5) 0.21780(10) 0.33913(15) 0.0218(4) Uani 1 1 d . . . C10 C 0.6077(5) 0.17401(10) 0.25850(15) 0.0222(4) Uani 1 1 d . . . C11 C 0.2919(6) 0.00220(11) 0.35566(18) 0.0329(5) Uani 1 1 d . . . H11A H 0.4448 -0.0238 0.3124 0.049 Uiso 1 1 calc R . . H11B H 0.0524 -0.0050 0.3318 0.049 Uiso 1 1 calc R . . H11C H 0.3228 -0.0132 0.4269 0.049 Uiso 1 1 calc R . . C12 C 0.2276(5) 0.42570(10) 0.43561(15) 0.0226(4) Uani 1 1 d . . . C13 C 0.0757(5) 0.47101(10) 0.51290(15) 0.0231(4) Uani 1 1 d . . . H13A H 0.0881 0.4578 0.5830 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 O1 0.0451(9) 0.0208(8) 0.0268(8) -0.0002(6) 0.0034(7) 0.0097(6) O2 0.0441(9) 0.0271(8) 0.0256(8) 0.0010(6) 0.0060(7) 0.0063(7) N1 0.0257(9) 0.0225(9) 0.0256(9) -0.0017(7) -0.0005(7) 0.0031(7) C2 0.0254(10) 0.0242(11) 0.0320(12) 0.0021(9) 0.0000(8) -0.0003(8) C3 0.0268(11) 0.0333(12) 0.0265(11) 0.0032(9) 0.0040(8) 0.0005(9) C4 0.0235(10) 0.0341(12) 0.0225(11) -0.0046(9) 0.0009(8) 0.0044(8) C5 0.0205(10) 0.0255(11) 0.0278(11) -0.0074(8) -0.0024(8) 0.0042(8) C6 0.0181(9) 0.0241(11) 0.0324(11) -0.0007(8) -0.0040(8) 0.0013(8) C7 0.0238(10) 0.0291(11) 0.0276(11) 0.0027(9) 0.0029(8) 0.0017(8) C8 0.0251(10) 0.0269(11) 0.0234(10) -0.0043(8) 0.0018(8) 0.0058(8) C9 0.0186(9) 0.0227(10) 0.0238(10) -0.0016(8) -0.0031(8) 0.0040(7) C10 0.0182(9) 0.0255(10) 0.0227(10) -0.0029(8) -0.0031(7) 0.0034(7) C11 0.0307(12) 0.0256(11) 0.0421(13) -0.0012(9) -0.0006(10) -0.0011(9) C12 0.0214(10) 0.0205(10) 0.0258(11) -0.0010(8) 0.0005(8) -0.0013(7) C13 0.0230(10) 0.0221(10) 0.0241(10) -0.0005(8) 0.0006(8) -0.0015(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.318(2) . ? O1 H1 1.03(3) . ? O2 C12 1.213(2) . ? N1 C2 1.315(3) . ? N1 C9 1.369(3) . ? C2 C3 1.402(3) . ? C2 H2A 0.9500 . ? C3 C4 1.365(3) . ? C3 H3A 0.9500 . ? C4 C10 1.413(3) . ? C4 H4A 0.9500 . ? C5 C6 1.372(3) . ? C5 C10 1.417(3) . ? C5 H5A 0.9500 . ? C6 C7 1.417(3) . ? C6 C11 1.505(3) . ? C7 C8 1.365(3) . ? C7 H7A 0.9500 . ? C8 C9 1.409(3) . ? C8 H8A 0.9500 . ? C9 C10 1.417(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.485(3) . ? C13 C13 1.318(4) 3_566 ? C13 H13A 0.9500 . ? 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 C12 O1 H1 109.5(19) . . ? C2 N1 C9 118.77(17) . . ? N1 C2 C3 123.07(19) . . ? N1 C2 H2A 118.5 . . ? C3 C2 H2A 118.5 . . ? C4 C3 C2 119.41(19) . . ? C4 C3 H3A 120.3 . . ? C2 C3 H3A 120.3 . . ? C3 C4 C10 119.49(18) . . ? C3 C4 H4A 120.3 . . ? C10 C4 H4A 120.3 . . ? C6 C5 C10 121.54(18) . . ? C6 C5 H5A 119.2 . . ? C10 C5 H5A 119.2 . . ? C5 C6 C7 118.43(18) . . ? C5 C6 C11 121.33(19) . . ? C7 C6 C11 120.23(19) . . ? C8 C7 C6 121.71(19) . . ? C8 C7 H7A 119.1 . . ? C6 C7 H7A 119.1 . . ? C7 C8 C9 120.19(18) . . ? C7 C8 H8A 119.9 . . ? C9 C8 H8A 119.9 . . ? N1 C9 C8 118.91(17) . . ? N1 C9 C10 121.82(18) . . ? C8 C9 C10 119.27(18) . . ? C4 C10 C9 117.43(18) . . ? C4 C10 C5 123.72(18) . . ? C9 C10 C5 118.85(18) . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C12 O1 124.34(18) . . ? O2 C12 C13 123.11(18) . . ? O1 C12 C13 112.55(17) . . ? C13 C13 C12 121.9(2) 3_566 . ? C13 C13 H13A 119.0 3_566 . ? C12 C13 H13A 119.0 . . ? 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 C9 N1 C2 C3 -0.2(3) . . . . ? N1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C10 0.9(3) . . . . ? C10 C5 C6 C7 -0.9(3) . . . . ? C10 C5 C6 C11 178.05(18) . . . . ? C5 C6 C7 C8 0.6(3) . . . . ? C11 C6 C7 C8 -178.36(19) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? C2 N1 C9 C8 -179.43(18) . . . . ? C2 N1 C9 C10 0.0(3) . . . . ? C7 C8 C9 N1 178.76(18) . . . . ? C7 C8 C9 C10 -0.7(3) . . . . ? C3 C4 C10 C9 -1.0(3) . . . . ? C3 C4 C10 C5 178.58(19) . . . . ? N1 C9 C10 C4 0.6(3) . . . . ? C8 C9 C10 C4 -179.95(17) . . . . ? N1 C9 C10 C5 -179.04(17) . . . . ? C8 C9 C10 C5 0.4(3) . . . . ? C6 C5 C10 C4 -179.19(18) . . . . ? C6 C5 C10 C9 0.4(3) . . . . ? O2 C12 C13 C13 6.0(4) . . . 3_566 ? O1 C12 C13 C13 -173.7(2) . . . 3_566 ? 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 1.03(3) 1.58(4) 2.607(2) 175(3) . #============================================================================= data_solid_solution _database_code_depnum_ccdc_archive 'CCDC 855814' #TrackingRef '- revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ; 75% 6-Methylquinoline/fumaric acid (2:1) 25% Quinoline/fumaric acid (2:1) ; _chemical_melting_point ? _chemical_formula_moiety '1.5(C10 H9 N), 0.5(C9 H7 N), C4 H4 O4' _chemical_formula_sum 'C23.50 H21 N2 O4' _chemical_formula_weight 395.42 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.8588(2) _cell_length_b 19.5187(11) _cell_length_c 13.0720(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.465(3) _cell_angle_gamma 90.00 _cell_volume 983.66(10) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2281 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 24.46 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.848 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 150(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 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 8601 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 25.06 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.984 _reflns_number_total 1725 _reflns_number_gt 1285 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0414P)^2^+0.3047P] 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 1725 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1011 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.164 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.037 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 0.3374(4) 0.36727(6) 0.47147(10) 0.0347(4) Uani 1 1 d . . . H1 H 0.427(8) 0.3366(15) 0.415(2) 0.101(10) Uiso 1 1 d . . . O2 O 0.2335(3) 0.44160(6) 0.34363(10) 0.0360(4) Uani 1 1 d . . . N1 N 0.5691(4) 0.28654(7) 0.33116(11) 0.0291(4) Uani 1 1 d . . . C2 C 0.7120(5) 0.31291(10) 0.25028(14) 0.0323(5) Uani 1 1 d . . . H2A H 0.7465 0.3611 0.2477 0.039 Uiso 1 1 calc R . . C3 C 0.8149(5) 0.27307(10) 0.16822(15) 0.0341(5) Uani 1 1 d . . . H3A H 0.9168 0.2941 0.1113 0.041 Uiso 1 1 calc R . . C4 C 0.7685(5) 0.20400(10) 0.17019(14) 0.0322(5) Uani 1 1 d . B . H4A H 0.8397 0.1765 0.1149 0.039 Uiso 1 1 calc R . . C5 C 0.5495(5) 0.10257(9) 0.26340(15) 0.0333(5) Uani 1 1 d . B . H5A H 0.6141 0.0726 0.2102 0.040 Uiso 1 1 calc R . . C6 C 0.3954(5) 0.07629(10) 0.34706(16) 0.0360(5) Uani 1 1 d . . . H6A H 0.3500 0.0281 0.3518 0.054 Uiso 0.25 1 d PR A 1 C11 C 0.3093(7) 0.00138(13) 0.3575(2) 0.0443(7) Uani 0.75 1 d P B 2 H11A H 0.4839 -0.0262 0.3239 0.066 Uiso 0.75 1 calc PR B 2 H11B H 0.0801 -0.0076 0.3252 0.066 Uiso 0.75 1 calc PR B 2 H11C H 0.3081 -0.0108 0.4302 0.066 Uiso 0.75 1 calc PR B 2 C7 C 0.3040(5) 0.12075(10) 0.42617(16) 0.0361(5) Uani 1 1 d . B . H7A H 0.1991 0.1025 0.4847 0.043 Uiso 1 1 calc R . . C8 C 0.3626(5) 0.18915(9) 0.42073(14) 0.0313(5) Uani 1 1 d . . . H8A H 0.2985 0.2182 0.4751 0.038 Uiso 1 1 calc R B . C9 C 0.5180(4) 0.21724(9) 0.33481(14) 0.0264(4) Uani 1 1 d . B . C10 C 0.6145(4) 0.17348(9) 0.25456(13) 0.0269(4) Uani 1 1 d . . . C12 C 0.2230(5) 0.42587(9) 0.43307(15) 0.0273(4) Uani 1 1 d . . . C13 C 0.0794(4) 0.47115(9) 0.51204(14) 0.0267(4) Uani 1 1 d . . . H13A H 0.1029 0.4580 0.5820 0.032 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 O1 0.0452(8) 0.0283(7) 0.0307(8) -0.0009(6) 0.0028(6) 0.0093(6) O2 0.0442(9) 0.0352(8) 0.0289(8) 0.0012(6) 0.0069(6) 0.0057(6) N1 0.0244(8) 0.0322(9) 0.0306(9) -0.0029(7) -0.0009(7) 0.0033(6) C2 0.0266(10) 0.0342(11) 0.0358(12) 0.0015(9) -0.0019(9) 0.0012(8) C3 0.0253(10) 0.0477(13) 0.0293(11) 0.0020(9) 0.0024(8) 0.0006(9) C4 0.0236(10) 0.0455(12) 0.0273(11) -0.0079(9) -0.0007(8) 0.0052(8) C5 0.0260(10) 0.0369(11) 0.0363(12) -0.0105(9) -0.0077(9) 0.0047(8) C6 0.0256(10) 0.0339(11) 0.0476(13) 0.0008(9) -0.0065(9) -0.0002(8) C11 0.0434(17) 0.0366(16) 0.0527(19) -0.0010(13) -0.0011(14) -0.0009(13) C7 0.0277(10) 0.0430(12) 0.0377(12) 0.0072(9) 0.0002(9) -0.0008(9) C8 0.0256(10) 0.0385(11) 0.0300(11) -0.0025(8) 0.0009(8) 0.0042(8) C9 0.0182(9) 0.0316(10) 0.0288(11) -0.0011(8) -0.0037(8) 0.0033(7) C10 0.0189(9) 0.0344(11) 0.0270(10) -0.0050(8) -0.0046(8) 0.0038(8) C12 0.0232(9) 0.0274(10) 0.0312(12) 0.0008(8) 0.0010(8) -0.0007(7) C13 0.0257(9) 0.0290(10) 0.0254(10) 0.0015(8) 0.0017(8) -0.0018(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.318(2) . ? O1 H1 1.02(3) . ? O2 C12 1.211(2) . ? N1 C2 1.318(2) . ? N1 C9 1.368(2) . ? C2 C3 1.396(3) . ? C2 H2A 0.9500 . ? C3 C4 1.360(3) . ? C3 H3A 0.9500 . ? C4 C10 1.407(3) . ? C4 H4A 0.9500 . ? C5 C6 1.367(3) . ? C5 C10 1.412(3) . ? C5 H5A 0.9500 . ? C6 C7 1.406(3) . ? C6 C11 1.507(3) . ? C6 H6A 0.9601 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C7 C8 1.356(3) . ? C7 H7A 0.9500 . ? C8 C9 1.407(3) . ? C8 H8A 0.9500 . ? C9 C10 1.415(2) . ? C12 C13 1.484(3) . ? C13 C13 1.314(3) 3_566 ? C13 H13A 0.9500 . ? 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 C12 O1 H1 110.6(16) . . ? C2 N1 C9 118.67(16) . . ? N1 C2 C3 122.79(18) . . ? N1 C2 H2A 118.6 . . ? C3 C2 H2A 118.6 . . ? C4 C3 C2 119.69(18) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? C3 C4 C10 119.64(17) . . ? C3 C4 H4A 120.2 . . ? C10 C4 H4A 120.2 . . ? C6 C5 C10 121.20(17) . . ? C6 C5 H5A 119.4 . . ? C10 C5 H5A 119.4 . . ? C5 C6 C7 119.22(18) . . ? C5 C6 C11 122.8(2) . . ? C7 C6 C11 118.0(2) . . ? C5 C6 H6A 120.4 . . ? C7 C6 H6A 120.3 . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C7 C6 121.41(19) . . ? C8 C7 H7A 119.3 . . ? C6 C7 H7A 119.3 . . ? C7 C8 C9 120.20(17) . . ? C7 C8 H8A 119.9 . . ? C9 C8 H8A 119.9 . . ? N1 C9 C8 118.69(16) . . ? N1 C9 C10 121.88(17) . . ? C8 C9 C10 119.43(16) . . ? C4 C10 C5 124.14(17) . . ? C4 C10 C9 117.32(17) . . ? C5 C10 C9 118.54(17) . . ? O2 C12 O1 124.27(17) . . ? O2 C12 C13 123.33(16) . . ? O1 C12 C13 112.39(16) . . ? C13 C13 C12 121.9(2) 3_566 . ? C13 C13 H13A 119.1 3_566 . ? C12 C13 H13A 119.1 . . ? 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 C9 N1 C2 C3 -0.2(3) . . . . ? N1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C10 0.6(3) . . . . ? C10 C5 C6 C7 -0.8(3) . . . . ? C10 C5 C6 C11 177.60(19) . . . . ? C5 C6 C7 C8 0.6(3) . . . . ? C11 C6 C7 C8 -177.82(19) . . . . ? C6 C7 C8 C9 0.0(3) . . . . ? C2 N1 C9 C8 -179.44(16) . . . . ? C2 N1 C9 C10 0.1(2) . . . . ? C7 C8 C9 N1 179.12(16) . . . . ? C7 C8 C9 C10 -0.4(3) . . . . ? C3 C4 C10 C5 178.92(17) . . . . ? C3 C4 C10 C9 -0.7(2) . . . . ? C6 C5 C10 C4 -179.28(17) . . . . ? C6 C5 C10 C9 0.3(2) . . . . ? N1 C9 C10 C4 0.4(2) . . . . ? C8 C9 C10 C4 179.90(15) . . . . ? N1 C9 C10 C5 -179.24(15) . . . . ? C8 C9 C10 C5 0.3(2) . . . . ? O2 C12 C13 C13 7.2(3) . . . 3_566 ? O1 C12 C13 C13 -173.0(2) . . . 3_566 ? 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 1.02(3) 1.59(3) 2.6052(19) 177(3) . #===END