Supplementary Material (ESI) for CrystEngComm This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 1350 _publ_contact_author_name 'Prof Ashwini Nangia' _publ_contact_author_address ; School of Chemistry University of Hyderabad Hyderabad 500 046 INDIA ; _publ_contact_author_email ansc@uohyd.ernet.in _publ_contact_author_phone '91 40 23011338' _publ_contact_author_fax '91 40 23011338' loop_ _publ_author_name 'Peddy Vishweshwar' 'Ashwini Nangia' 'Vincent M. Lynch' _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Supramolecular synthons in phenol isonicotinamide adducts ; data_hbain _database_code_CSD 208482 _audit_creation_method SHELXL-97 _exptl_crystal_preparation Methanol _chemical_name_systematic ; 1:1 molecular complex of 4-hydroxybenzoic acid and isonicotinamide ; _chemical_name_common '1:1 molecular complex of 4-hydroxybenzoic acid and isonicotinamide' _chemical_melting_point '468 K' _chemical_formula_moiety 'C7 H6 O3, C6 H6 N2 O' _chemical_formula_sum 'C13 H12 N2 O4' _chemical_formula_weight 260.25 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/n' _symmetry_space_group_name_Hall '-P 2yn' 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 6.0729(1) _cell_length_b 9.4013(2) _cell_length_c 20.6723(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.2870(10) _cell_angle_gamma 90.00 _cell_volume 1175.23(4) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2684 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 27.49 _exptl_crystal_description needles _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal focus for the X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\w scans' _diffrn_standards_decay_% 'less than 1' _diffrn_reflns_number 4946 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2684 _reflns_number_gt 1952 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect data collection software, Nonius 1998' _computing_cell_refinement 'DENZO-SMN (Z. Otwinowski and W. Minor, 1997)' _computing_data_reduction 'SCALEPACK (Z. Otwinowski and W. Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTON (Spek, 1992)' _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^)+(0.0483P)^2^+0.3250P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.024(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2684 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 N1 N -0.0985(2) 1.08930(14) 0.34967(6) 0.0332(3) Uani 1 1 d . . . C2 C -0.2174(3) 0.97934(18) 0.36822(8) 0.0364(4) Uani 1 1 d . . . C3 C -0.1363(3) 0.87545(18) 0.41114(7) 0.0336(4) Uani 1 1 d . . . C4 C 0.0818(2) 0.88440(15) 0.43706(7) 0.0250(3) Uani 1 1 d . . . C5 C 0.2065(3) 0.99909(16) 0.41894(7) 0.0301(4) Uani 1 1 d . . . C6 C 0.1116(3) 1.09718(17) 0.37494(8) 0.0327(4) Uani 1 1 d . . . C7 C 0.1911(2) 0.77682(16) 0.48268(7) 0.0267(3) Uani 1 1 d . . . O8 O 0.39183(17) 0.78854(12) 0.49953(5) 0.0394(3) Uani 1 1 d . . . N9 N 0.0718(2) 0.67111(15) 0.50355(7) 0.0353(3) Uani 1 1 d . . . C10 C 0.7047(2) 0.43058(15) 0.64595(7) 0.0248(3) Uani 1 1 d . . . C11 C 0.9192(2) 0.47915(16) 0.66212(7) 0.0262(3) Uani 1 1 d . . . C12 C 1.0585(2) 0.41088(16) 0.70893(7) 0.0284(3) Uani 1 1 d . . . C13 C 0.9847(2) 0.29074(16) 0.73992(7) 0.0291(4) Uani 1 1 d . . . C14 C 0.7726(3) 0.23928(17) 0.72322(7) 0.0317(4) Uani 1 1 d . . . C15 C 0.6333(3) 0.30943(16) 0.67714(7) 0.0290(4) Uani 1 1 d . . . C16 C 0.5511(2) 0.50483(15) 0.59742(7) 0.0253(3) Uani 1 1 d . . . O17 O 0.36131(16) 0.46688(11) 0.58157(5) 0.0324(3) Uani 1 1 d . . . O18 O 0.64006(18) 0.61907(11) 0.57227(5) 0.0342(3) Uani 1 1 d . . . O19 O 1.1142(2) 0.21998(12) 0.78659(5) 0.0396(3) Uani 1 1 d . . . H2 H -0.369(3) 0.9771(18) 0.3502(8) 0.037(4) Uiso 1 1 d . . . H3 H -0.231(3) 0.798(2) 0.4221(8) 0.046(5) Uiso 1 1 d . . . H5 H 0.359(3) 1.0084(17) 0.4379(8) 0.033(4) Uiso 1 1 d . . . H6 H 0.198(3) 1.179(2) 0.3610(8) 0.042(5) Uiso 1 1 d . . . H9A H 0.149(3) 0.600(2) 0.5320(10) 0.064(6) Uiso 1 1 d . . . H9B H -0.077(4) 0.667(2) 0.4927(10) 0.062(6) Uiso 1 1 d . . . H11 H 0.975(3) 0.5633(19) 0.6409(8) 0.037(4) Uiso 1 1 d . . . H12 H 1.210(3) 0.4464(18) 0.7198(8) 0.035(4) Uiso 1 1 d . . . H14 H 0.721(3) 0.153(2) 0.7451(8) 0.046(5) Uiso 1 1 d . . . H15 H 0.477(3) 0.2766(17) 0.6666(8) 0.034(4) Uiso 1 1 d . . . H18 H 0.525(4) 0.679(2) 0.5448(10) 0.070(6) Uiso 1 1 d . . . H19 H 1.233(4) 0.283(2) 0.8037(10) 0.074(7) 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 0.0317(7) 0.0304(7) 0.0358(7) -0.0013(6) -0.0056(6) -0.0013(6) C2 0.0250(8) 0.0408(10) 0.0417(9) 0.0009(7) -0.0066(7) -0.0034(7) C3 0.0274(8) 0.0375(9) 0.0351(9) 0.0020(7) -0.0005(7) -0.0094(7) C4 0.0254(7) 0.0267(8) 0.0229(7) -0.0038(6) 0.0024(6) -0.0026(6) C5 0.0253(8) 0.0308(9) 0.0330(8) 0.0010(6) -0.0027(6) -0.0038(6) C6 0.0330(9) 0.0277(8) 0.0363(8) 0.0011(7) -0.0029(7) -0.0069(7) C7 0.0276(8) 0.0283(8) 0.0241(7) -0.0026(6) 0.0027(6) -0.0049(6) O8 0.0288(6) 0.0401(7) 0.0469(7) 0.0140(5) -0.0101(5) -0.0105(5) N9 0.0285(7) 0.0335(8) 0.0442(8) 0.0088(6) 0.0047(6) -0.0057(6) C10 0.0256(7) 0.0263(8) 0.0225(7) -0.0025(6) 0.0024(6) -0.0005(6) C11 0.0262(8) 0.0261(8) 0.0267(7) 0.0002(6) 0.0042(6) -0.0014(6) C12 0.0243(8) 0.0295(8) 0.0311(8) -0.0016(6) 0.0007(6) -0.0007(6) C13 0.0316(8) 0.0277(8) 0.0269(7) -0.0018(6) -0.0025(6) 0.0032(6) C14 0.0366(9) 0.0277(8) 0.0301(8) 0.0025(7) -0.0005(7) -0.0064(7) C15 0.0272(8) 0.0302(8) 0.0289(8) -0.0009(6) -0.0007(6) -0.0045(7) C16 0.0253(7) 0.0266(8) 0.0242(7) -0.0021(6) 0.0032(6) -0.0026(6) O17 0.0264(6) 0.0346(6) 0.0351(6) 0.0045(5) -0.0032(4) -0.0061(5) O18 0.0276(6) 0.0347(6) 0.0389(6) 0.0112(5) -0.0033(5) -0.0073(5) O19 0.0422(7) 0.0312(6) 0.0420(6) 0.0062(5) -0.0149(5) -0.0021(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 N1 C6 1.335(2) . ? N1 C2 1.337(2) . ? C2 C3 1.380(2) . ? C2 H2 0.960(16) . ? C3 C4 1.385(2) . ? C3 H3 0.969(19) . ? C4 C5 1.389(2) . ? C4 C7 1.496(2) . ? C5 C6 1.383(2) . ? C5 H5 0.978(16) . ? C6 H6 0.991(18) . ? C7 O8 1.2413(17) . ? C7 N9 1.3254(19) . ? N9 H9A 0.98(2) . ? N9 H9B 0.91(2) . ? C10 C11 1.392(2) . ? C10 C15 1.397(2) . ? C10 C16 1.480(2) . ? C11 C12 1.383(2) . ? C11 H11 0.979(18) . ? C12 C13 1.393(2) . ? C12 H12 0.983(17) . ? C13 O19 1.3607(17) . ? C13 C14 1.390(2) . ? C14 C15 1.382(2) . ? C14 H14 0.994(19) . ? C15 H15 1.004(17) . ? C16 O17 1.2220(17) . ? C16 O18 1.3295(17) . ? O18 H18 1.03(2) . ? O19 H19 0.98(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 C6 N1 C2 116.91(14) . . ? N1 C2 C3 124.15(15) . . ? N1 C2 H2 115.4(10) . . ? C3 C2 H2 120.4(10) . . ? C2 C3 C4 118.55(15) . . ? C2 C3 H3 120.0(11) . . ? C4 C3 H3 121.4(11) . . ? C3 C4 C5 117.95(14) . . ? C3 C4 C7 123.77(13) . . ? C5 C4 C7 118.28(13) . . ? C6 C5 C4 119.38(14) . . ? C6 C5 H5 121.8(9) . . ? C4 C5 H5 118.8(9) . . ? N1 C6 C5 123.04(15) . . ? N1 C6 H6 116.3(10) . . ? C5 C6 H6 120.7(10) . . ? O8 C7 N9 121.83(14) . . ? O8 C7 C4 118.95(13) . . ? N9 C7 C4 119.21(14) . . ? C7 N9 H9A 117.2(12) . . ? C7 N9 H9B 120.9(13) . . ? H9A N9 H9B 121.9(18) . . ? C11 C10 C15 118.68(13) . . ? C11 C10 C16 121.69(13) . . ? C15 C10 C16 119.63(13) . . ? C12 C11 C10 120.96(14) . . ? C12 C11 H11 118.3(10) . . ? C10 C11 H11 120.7(10) . . ? C11 C12 C13 119.74(14) . . ? C11 C12 H12 120.0(10) . . ? C13 C12 H12 120.2(10) . . ? O19 C13 C14 117.89(14) . . ? O19 C13 C12 122.23(14) . . ? C14 C13 C12 119.88(14) . . ? C15 C14 C13 119.99(14) . . ? C15 C14 H14 120.4(11) . . ? C13 C14 H14 119.6(11) . . ? C14 C15 C10 120.72(14) . . ? C14 C15 H15 120.6(9) . . ? C10 C15 H15 118.6(9) . . ? O17 C16 O18 122.56(13) . . ? O17 C16 C10 124.32(13) . . ? O18 C16 C10 113.12(12) . . ? C16 O18 H18 112.5(12) . . ? C13 O19 H19 108.7(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 C3 -0.1(2) . . . . ? N1 C2 C3 C4 0.0(3) . . . . ? C2 C3 C4 C5 0.8(2) . . . . ? C2 C3 C4 C7 -178.38(14) . . . . ? C3 C4 C5 C6 -1.6(2) . . . . ? C7 C4 C5 C6 177.62(14) . . . . ? C2 N1 C6 C5 -0.8(2) . . . . ? C4 C5 C6 N1 1.7(2) . . . . ? C3 C4 C7 O8 174.73(15) . . . . ? C5 C4 C7 O8 -4.5(2) . . . . ? C3 C4 C7 N9 -4.7(2) . . . . ? C5 C4 C7 N9 176.09(14) . . . . ? C15 C10 C11 C12 -1.2(2) . . . . ? C16 C10 C11 C12 178.12(13) . . . . ? C10 C11 C12 C13 0.8(2) . . . . ? C11 C12 C13 O19 -179.57(13) . . . . ? C11 C12 C13 C14 0.6(2) . . . . ? O19 C13 C14 C15 178.53(13) . . . . ? C12 C13 C14 C15 -1.7(2) . . . . ? C13 C14 C15 C10 1.3(2) . . . . ? C11 C10 C15 C14 0.1(2) . . . . ? C16 C10 C15 C14 -179.18(13) . . . . ? C11 C10 C16 O17 -179.86(14) . . . . ? C15 C10 C16 O17 -0.6(2) . . . . ? C11 C10 C16 O18 -0.02(19) . . . . ? C15 C10 C16 O18 179.25(12) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.192 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.042 data_rein _database_code_CSD 208483 _audit_creation_method SHELXL-97 _exptl_crystal_preparation 'Ethyl acetate' _chemical_name_systematic ; 1:2 molecular complex of resorcinol and isonicotinamide ; _chemical_name_common '1:2 molecular complex of resorcinol and isonicotinamide' _chemical_melting_point '428 K' _chemical_formula_moiety '2(C6 H6 N2 O), C6 H6 O2' _chemical_formula_sum 'C18 H18 N4 O4' _chemical_formula_weight 354.36 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 7.0307(1) _cell_length_b 10.7052(2) _cell_length_c 11.9562(2) _cell_angle_alpha 87.7550(10) _cell_angle_beta 82.7350(10) _cell_angle_gamma 73.8350(10) _cell_volume 857.36(2) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4462 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 30.52 _exptl_crystal_description Needle _exptl_crystal_colour 'Light brown' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal focus for the X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\w scans' _diffrn_standards_decay_% 'less than 1' _diffrn_reflns_number 7843 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 30.52 _reflns_number_total 4462 _reflns_number_gt 3324 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect data collection software, Nonius 1998' _computing_cell_refinement 'DENZO-SMN (Z. Otwinowski and W. Minor, 1997)' _computing_data_reduction 'SCALEPACK (Z. Otwinowski and W. Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTON (Spek, 1992)' _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^)+(0.0571P)^2^+0.1187P] 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 refall _refine_ls_extinction_method none _refine_ls_number_reflns 4462 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.1043 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 C1 C 0.50790(17) 0.59127(12) 0.26070(10) 0.0237(3) Uani 1 1 d . . . C2 C 0.60505(17) 0.68788(11) 0.26245(10) 0.0222(3) Uani 1 1 d . . . C3 C 0.75178(17) 0.69709(11) 0.17537(10) 0.0216(3) Uani 1 1 d . . . C4 C 0.79637(18) 0.61281(12) 0.08422(10) 0.0255(3) Uani 1 1 d . . . C5 C 0.69482(19) 0.51859(13) 0.08281(11) 0.0287(3) Uani 1 1 d . . . C6 C 0.55196(19) 0.50568(12) 0.17066(11) 0.0277(3) Uani 1 1 d . . . O7 O 0.37138(14) 0.58623(9) 0.35078(8) 0.0340(2) Uani 1 1 d . . . O8 O 0.84713(13) 0.79116(9) 0.18333(8) 0.0279(2) Uani 1 1 d . . . N9 N 1.11631(15) 0.81390(10) 0.00434(9) 0.0263(2) Uani 1 1 d . . . C10 C 1.06819(19) 0.84622(13) -0.09970(11) 0.0289(3) Uani 1 1 d . . . C11 C 1.19294(18) 0.88694(12) -0.18365(11) 0.0255(3) Uani 1 1 d . . . C12 C 1.37599(17) 0.89625(11) -0.15910(10) 0.0206(2) Uani 1 1 d . . . C13 C 1.42777(19) 0.86149(12) -0.05185(10) 0.0256(3) Uani 1 1 d . . . C14 C 1.29486(19) 0.82027(13) 0.02673(11) 0.0271(3) Uani 1 1 d . . . C15 C 1.51759(17) 0.94800(11) -0.24117(10) 0.0219(3) Uani 1 1 d . . . O16 O 1.65861(13) 0.97597(10) -0.20630(7) 0.0322(2) Uani 1 1 d . . . N17 N 1.48311(17) 0.96354(11) -0.34821(9) 0.0268(2) Uani 1 1 d . . . N18 N 0.16802(16) 0.40280(11) 0.37113(9) 0.0296(3) Uani 1 1 d . . . C19 C 0.2404(2) 0.33187(14) 0.45847(12) 0.0326(3) Uani 1 1 d . . . C20 C 0.14590(19) 0.24883(13) 0.51939(12) 0.0295(3) Uani 1 1 d . . . C21 C -0.03336(17) 0.23860(11) 0.48983(10) 0.0213(3) Uani 1 1 d . . . C22 C -0.10990(19) 0.31170(13) 0.39912(11) 0.0277(3) Uani 1 1 d . . . C23 C -0.0045(2) 0.39170(13) 0.34222(12) 0.0309(3) Uani 1 1 d . . . C24 C -0.14597(17) 0.15242(11) 0.55411(10) 0.0217(3) Uani 1 1 d . . . O25 O -0.26651(13) 0.11196(9) 0.50893(7) 0.0296(2) Uani 1 1 d . . . N26 N -0.10692(16) 0.12095(11) 0.65912(9) 0.0250(2) Uani 1 1 d . . . H14 H 1.332(2) 0.7952(14) 0.1047(13) 0.035(4) Uiso 1 1 d . . . H4 H 0.900(2) 0.6204(14) 0.0209(12) 0.031(4) Uiso 1 1 d . . . H2 H 0.571(2) 0.7485(14) 0.3255(12) 0.029(4) Uiso 1 1 d . . . H22 H -0.239(2) 0.3079(15) 0.3752(13) 0.040(4) Uiso 1 1 d . . . H13 H 1.555(2) 0.8659(14) -0.0298(12) 0.035(4) Uiso 1 1 d . . . H19 H 0.365(2) 0.3426(15) 0.4833(13) 0.041(4) Uiso 1 1 d . . . H6 H 0.483(2) 0.4359(15) 0.1703(12) 0.036(4) Uiso 1 1 d . . . H11 H 1.146(2) 0.9100(14) -0.2581(13) 0.030(4) Uiso 1 1 d . . . H10 H 0.934(2) 0.8415(16) -0.1145(13) 0.042(4) Uiso 1 1 d . . . H20 H 0.202(2) 0.2017(16) 0.5851(14) 0.041(4) Uiso 1 1 d . . . H23 H -0.057(2) 0.4444(15) 0.2772(13) 0.038(4) Uiso 1 1 d . . . H7 H 0.304(3) 0.527(2) 0.3396(16) 0.064(6) Uiso 1 1 d . . . H26B H -0.184(2) 0.0721(16) 0.7001(14) 0.040(4) Uiso 1 1 d . . . H26A H -0.031(2) 0.1598(15) 0.6940(13) 0.039(4) Uiso 1 1 d . . . H17B H 1.389(2) 0.9343(16) -0.3767(14) 0.042(4) Uiso 1 1 d . . . H5 H 0.727(2) 0.4574(15) 0.0186(13) 0.038(4) Uiso 1 1 d . . . H17A H 1.572(2) 0.9986(16) -0.3952(14) 0.042(4) Uiso 1 1 d . . . H8 H 0.936(3) 0.7917(18) 0.1151(16) 0.059(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 C1 0.0204(6) 0.0252(6) 0.0261(6) 0.0047(5) -0.0008(5) -0.0088(5) C2 0.0228(6) 0.0241(6) 0.0216(6) 0.0005(5) -0.0013(5) -0.0102(5) C3 0.0214(6) 0.0224(6) 0.0231(6) 0.0035(5) -0.0043(5) -0.0094(5) C4 0.0241(6) 0.0295(6) 0.0232(6) 0.0006(5) 0.0012(5) -0.0096(5) C5 0.0300(7) 0.0283(7) 0.0284(7) -0.0052(5) -0.0013(5) -0.0093(5) C6 0.0281(7) 0.0250(6) 0.0334(7) 0.0005(5) -0.0030(5) -0.0130(5) O7 0.0354(5) 0.0360(5) 0.0342(5) -0.0011(4) 0.0106(4) -0.0222(4) O8 0.0307(5) 0.0326(5) 0.0260(5) -0.0011(4) 0.0033(4) -0.0210(4) N9 0.0267(5) 0.0281(6) 0.0269(6) 0.0045(4) -0.0013(4) -0.0137(4) C10 0.0235(6) 0.0352(7) 0.0318(7) 0.0071(5) -0.0046(5) -0.0147(5) C11 0.0238(6) 0.0308(7) 0.0256(6) 0.0065(5) -0.0072(5) -0.0125(5) C12 0.0224(6) 0.0202(6) 0.0214(6) 0.0023(4) -0.0021(4) -0.0099(5) C13 0.0259(6) 0.0323(7) 0.0232(6) 0.0055(5) -0.0058(5) -0.0152(5) C14 0.0313(7) 0.0315(7) 0.0224(6) 0.0049(5) -0.0037(5) -0.0155(5) C15 0.0231(6) 0.0238(6) 0.0212(6) 0.0028(4) -0.0026(5) -0.0110(5) O16 0.0318(5) 0.0482(6) 0.0263(5) 0.0108(4) -0.0082(4) -0.0264(4) N17 0.0309(6) 0.0369(6) 0.0190(5) 0.0032(4) -0.0028(4) -0.0207(5) N18 0.0287(6) 0.0312(6) 0.0313(6) 0.0055(5) 0.0010(5) -0.0151(5) C19 0.0275(7) 0.0408(8) 0.0360(8) 0.0102(6) -0.0056(6) -0.0209(6) C20 0.0274(7) 0.0374(7) 0.0290(7) 0.0100(6) -0.0071(5) -0.0173(6) C21 0.0225(6) 0.0241(6) 0.0193(6) 0.0000(4) 0.0000(4) -0.0111(5) C22 0.0262(6) 0.0336(7) 0.0270(7) 0.0057(5) -0.0052(5) -0.0142(5) C23 0.0307(7) 0.0347(7) 0.0294(7) 0.0106(6) -0.0044(5) -0.0138(6) C24 0.0222(6) 0.0237(6) 0.0216(6) 0.0016(4) -0.0022(5) -0.0106(5) O25 0.0345(5) 0.0405(5) 0.0231(5) 0.0047(4) -0.0068(4) -0.0250(4) N26 0.0277(6) 0.0315(6) 0.0217(5) 0.0061(4) -0.0046(4) -0.0181(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 C1 O7 1.3590(14) . ? C1 C6 1.3890(18) . ? C1 C2 1.3912(16) . ? C2 C3 1.3910(16) . ? C2 H2 0.976(15) . ? C3 O8 1.3682(14) . ? C3 C4 1.3903(17) . ? C4 C5 1.3903(18) . ? C4 H4 1.002(14) . ? C5 C6 1.3893(18) . ? C5 H5 0.992(16) . ? C6 H6 0.998(15) . ? O7 H7 0.91(2) . ? O8 H8 0.965(19) . ? N9 C14 1.3365(16) . ? N9 C10 1.3376(17) . ? C10 C11 1.3867(17) . ? C10 H10 0.994(16) . ? C11 C12 1.3862(16) . ? C11 H11 0.987(15) . ? C12 C13 1.3859(17) . ? C12 C15 1.5094(15) . ? C13 C14 1.3876(16) . ? C13 H13 0.979(15) . ? C14 H14 1.007(15) . ? C15 O16 1.2353(14) . ? C15 N17 1.3280(15) . ? N17 H17B 0.912(17) . ? N17 H17A 0.934(17) . ? N18 C19 1.3353(18) . ? N18 C23 1.3392(17) . ? C19 C20 1.3846(17) . ? C19 H19 0.993(16) . ? C20 C21 1.3849(17) . ? C20 H20 0.981(16) . ? C21 C22 1.3874(17) . ? C21 C24 1.5053(15) . ? C22 C23 1.3879(17) . ? C22 H22 1.001(16) . ? C23 H23 0.992(16) . ? C24 O25 1.2393(14) . ? C24 N26 1.3296(15) . ? N26 H26B 0.935(17) . ? N26 H26A 0.908(16) . ? 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 O7 C1 C6 123.10(11) . . ? O7 C1 C2 116.43(11) . . ? C6 C1 C2 120.48(11) . . ? C3 C2 C1 120.13(11) . . ? C3 C2 H2 120.2(8) . . ? C1 C2 H2 119.7(8) . . ? O8 C3 C4 122.34(10) . . ? O8 C3 C2 117.64(10) . . ? C4 C3 C2 120.03(11) . . ? C3 C4 C5 119.01(11) . . ? C3 C4 H4 120.0(8) . . ? C5 C4 H4 121.0(8) . . ? C6 C5 C4 121.67(12) . . ? C6 C5 H5 119.0(9) . . ? C4 C5 H5 119.3(9) . . ? C1 C6 C5 118.64(11) . . ? C1 C6 H6 120.1(9) . . ? C5 C6 H6 121.2(9) . . ? C1 O7 H7 111.1(12) . . ? C3 O8 H8 109.1(11) . . ? C14 N9 C10 117.60(10) . . ? N9 C10 C11 123.23(11) . . ? N9 C10 H10 116.4(9) . . ? C11 C10 H10 120.4(9) . . ? C12 C11 C10 118.88(12) . . ? C12 C11 H11 122.7(8) . . ? C10 C11 H11 118.4(8) . . ? C13 C12 C11 118.19(11) . . ? C13 C12 C15 118.26(10) . . ? C11 C12 C15 123.48(11) . . ? C12 C13 C14 119.15(11) . . ? C12 C13 H13 121.8(9) . . ? C14 C13 H13 119.1(9) . . ? N9 C14 C13 122.93(12) . . ? N9 C14 H14 117.9(8) . . ? C13 C14 H14 119.2(8) . . ? O16 C15 N17 122.60(11) . . ? O16 C15 C12 119.10(10) . . ? N17 C15 C12 118.29(10) . . ? C15 N17 H17B 123.3(10) . . ? C15 N17 H17A 115.2(10) . . ? H17B N17 H17A 121.1(14) . . ? C19 N18 C23 117.47(11) . . ? N18 C19 C20 123.24(12) . . ? N18 C19 H19 118.3(9) . . ? C20 C19 H19 118.4(9) . . ? C19 C20 C21 119.08(12) . . ? C19 C20 H20 120.2(9) . . ? C21 C20 H20 120.6(9) . . ? C20 C21 C22 118.21(11) . . ? C20 C21 C24 121.77(11) . . ? C22 C21 C24 120.02(10) . . ? C21 C22 C23 118.87(12) . . ? C21 C22 H22 120.9(9) . . ? C23 C22 H22 120.2(9) . . ? N18 C23 C22 123.13(12) . . ? N18 C23 H23 117.2(9) . . ? C22 C23 H23 119.7(9) . . ? O25 C24 N26 122.53(11) . . ? O25 C24 C21 120.50(10) . . ? N26 C24 C21 116.96(10) . . ? C24 N26 H26B 116.4(10) . . ? C24 N26 H26A 121.2(10) . . ? H26B N26 H26A 121.0(14) . . ? _diffrn_measured_fraction_theta_max 0.853 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.853 _refine_diff_density_max 0.395 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.046 data_pgin _database_code_CSD 208484 _audit_creation_method SHELXL-97 _exptl_crystal_preparation Acetone _chemical_name_systematic ; 1:2 molecular complex of phloroglucinol and isonicotinamide dihydrate ; _chemical_name_common '1:2 molecular complex of phloroglucinol and isonicotinamide dihydrate' _chemical_melting_point '417 K' _chemical_formula_moiety '2(C6 H6 N2 O), C6 H6 O3, 2(H2 O)' _chemical_formula_sum 'C18 H22 N4 O7' _chemical_formula_weight 406.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 7.4967(1) _cell_length_b 8.8748(1) _cell_length_c 15.2793(3) _cell_angle_alpha 95.1886(6) _cell_angle_beta 97.4790(6) _cell_angle_gamma 105.7701(7) _cell_volume 961.50(3) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4275 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.52 _exptl_crystal_description Lathes _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal focus for the X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\w scans' _diffrn_standards_decay_% 'less than 1' _diffrn_reflns_number 6903 _diffrn_reflns_av_R_equivalents 0.0137 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.52 _reflns_number_total 4275 _reflns_number_gt 3583 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect data collection software, Nonius 1998' _computing_cell_refinement 'DENZO-SMN (Z. Otwinowski and W. Minor, 1997)' _computing_data_reduction 'SCALEPACK (Z. Otwinowski and W. Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTON (Spek, 1992)' _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^)+(0.0481P)^2^+0.2279P] 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 refall _refine_ls_extinction_method none _refine_ls_number_reflns 4275 _refine_ls_number_parameters 350 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0988 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 O28 O 0.82310(11) 0.33498(10) 0.12632(6) 0.02310(19) Uani 1 1 d . . . N17 N 0.77754(13) 0.24287(11) -0.05698(6) 0.0221(2) Uani 1 1 d . . . O29 O 0.44715(12) 0.41768(10) 0.34461(5) 0.0260(2) Uani 1 1 d . . . O27 O 0.16483(12) 0.27472(11) 0.04359(6) 0.0277(2) Uani 1 1 d . . . N8 N 0.21727(14) 0.14953(12) -0.11954(6) 0.0235(2) Uani 1 1 d . . . O20 O 0.82756(14) 0.21482(10) -0.38149(6) 0.0310(2) Uani 1 1 d . . . O11 O 0.27206(14) 0.10941(10) -0.44248(6) 0.0323(2) Uani 1 1 d . . . C22 C 0.49540(16) 0.30644(13) 0.08086(7) 0.0196(2) Uani 1 1 d . . . N19 N 0.68935(17) -0.04012(13) -0.37208(7) 0.0298(3) Uani 1 1 d . . . C24 C 0.64078(16) 0.37610(13) 0.23602(7) 0.0197(2) Uani 1 1 d . . . C5 C 0.21427(16) 0.04926(13) -0.29857(7) 0.0202(2) Uani 1 1 d . . . C25 C 0.46818(16) 0.38268(12) 0.25757(7) 0.0191(2) Uani 1 1 d . . . C26 C 0.30858(16) 0.35001(13) 0.19337(7) 0.0205(2) Uani 1 1 d . . . N10 N 0.15482(16) -0.14763(12) -0.42908(7) 0.0287(2) Uani 1 1 d . . . C14 C 0.76239(15) 0.15215(13) -0.23865(7) 0.0194(2) Uani 1 1 d . . . C23 C 0.65303(15) 0.33843(12) 0.14674(7) 0.0184(2) Uani 1 1 d . . . C13 C 0.85872(17) 0.30424(14) -0.19887(8) 0.0231(2) Uani 1 1 d . . . C12 C 0.86142(17) 0.34459(14) -0.10875(8) 0.0239(3) Uani 1 1 d . . . C9 C 0.21465(16) 0.00442(14) -0.39615(7) 0.0227(2) Uani 1 1 d . . . C15 C 0.67262(17) 0.04606(14) -0.18568(8) 0.0229(2) Uani 1 1 d . . . C18 C 0.76121(16) 0.11042(13) -0.33671(7) 0.0214(2) Uani 1 1 d . . . C7 C 0.12688(17) 0.00103(14) -0.15612(8) 0.0238(3) Uani 1 1 d . . . C6 C 0.12332(17) -0.05406(14) -0.24471(8) 0.0232(2) Uani 1 1 d . . . C21 C 0.32361(16) 0.31000(13) 0.10491(7) 0.0200(2) Uani 1 1 d . . . C16 C 0.68492(17) 0.09631(14) -0.09564(8) 0.0243(3) Uani 1 1 d . . . C4 C 0.31010(17) 0.20303(14) -0.26045(8) 0.0238(3) Uani 1 1 d . . . C3 C 0.30868(18) 0.24737(14) -0.17138(8) 0.0256(3) Uani 1 1 d . . . O2 O 0.77121(14) 0.58461(11) 0.43841(6) 0.0322(2) Uani 1 1 d . . . O1 O 0.10642(14) 0.45000(11) 0.38567(6) 0.0281(2) Uani 1 1 d . . . H22 H 0.505(2) 0.2795(16) 0.0176(10) 0.028(4) Uiso 1 1 d . . . H7 H 0.0645(19) -0.0681(16) -0.1181(9) 0.025(3) Uiso 1 1 d . . . H12 H 0.925(2) 0.4480(18) -0.0804(10) 0.031(4) Uiso 1 1 d . . . H15 H 0.603(2) -0.0610(18) -0.2070(10) 0.030(4) Uiso 1 1 d . . . H4 H 0.375(2) 0.2771(17) -0.2945(10) 0.030(4) Uiso 1 1 d . . . H3 H 0.374(2) 0.3510(19) -0.1435(10) 0.037(4) Uiso 1 1 d . . . H19B H 0.693(2) -0.0624(19) -0.4309(12) 0.041(4) Uiso 1 1 d . . . H27 H 0.190(2) 0.230(2) -0.0114(12) 0.051(5) Uiso 1 1 d . . . H16 H 0.625(2) 0.0212(18) -0.0585(9) 0.029(4) Uiso 1 1 d . . . H26 H 0.190(2) 0.3548(16) 0.2094(9) 0.027(3) Uiso 1 1 d . . . H10B H 0.155(2) -0.1712(18) -0.4890(12) 0.040(4) Uiso 1 1 d . . . H6 H 0.055(2) -0.1626(18) -0.2655(10) 0.031(4) Uiso 1 1 d . . . H13 H 0.927(2) 0.3803(18) -0.2327(10) 0.033(4) Uiso 1 1 d . . . H24 H 0.753(2) 0.3994(16) 0.2804(9) 0.026(3) Uiso 1 1 d . . . H10A H 0.107(2) -0.222(2) -0.3973(11) 0.039(4) Uiso 1 1 d . . . H28 H 0.807(2) 0.304(2) 0.0659(12) 0.048(5) Uiso 1 1 d . . . H19A H 0.650(2) -0.114(2) -0.3386(11) 0.042(4) Uiso 1 1 d . . . H1A H 0.098(2) 0.547(2) 0.3821(12) 0.050(5) Uiso 1 1 d . . . H2A H 0.764(3) 0.684(3) 0.4398(13) 0.062(6) Uiso 1 1 d . . . H29 H 0.560(3) 0.468(2) 0.3778(12) 0.055(5) Uiso 1 1 d . . . H1B H 0.218(3) 0.448(2) 0.3684(13) 0.061(6) Uiso 1 1 d . . . H2B H 0.808(3) 0.572(2) 0.4921(15) 0.063(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 O28 0.0196(4) 0.0289(4) 0.0200(4) 0.0006(3) 0.0049(3) 0.0057(3) N17 0.0225(5) 0.0254(5) 0.0191(5) 0.0021(4) 0.0044(4) 0.0075(4) O29 0.0275(5) 0.0344(5) 0.0138(4) -0.0011(3) 0.0048(3) 0.0057(4) O27 0.0221(4) 0.0416(5) 0.0179(4) -0.0043(4) -0.0007(3) 0.0112(4) N8 0.0287(5) 0.0254(5) 0.0172(5) 0.0004(4) 0.0007(4) 0.0113(4) O20 0.0477(6) 0.0230(4) 0.0196(4) 0.0022(3) 0.0098(4) 0.0039(4) O11 0.0523(6) 0.0226(4) 0.0207(4) 0.0028(4) 0.0108(4) 0.0061(4) C22 0.0238(6) 0.0201(5) 0.0144(5) -0.0001(4) 0.0038(4) 0.0059(4) N19 0.0457(7) 0.0220(5) 0.0185(5) 0.0002(4) 0.0077(5) 0.0038(5) C24 0.0219(6) 0.0183(5) 0.0169(5) 0.0018(4) 0.0007(4) 0.0038(4) C5 0.0219(5) 0.0216(5) 0.0173(5) 0.0014(4) 0.0010(4) 0.0081(4) C25 0.0260(6) 0.0157(5) 0.0145(5) 0.0011(4) 0.0046(4) 0.0038(4) C26 0.0216(6) 0.0216(5) 0.0186(6) 0.0006(4) 0.0054(4) 0.0066(4) N10 0.0427(6) 0.0221(5) 0.0174(5) -0.0006(4) 0.0069(5) 0.0031(5) C14 0.0207(5) 0.0202(5) 0.0185(5) 0.0017(4) 0.0031(4) 0.0082(4) C23 0.0203(5) 0.0143(5) 0.0203(6) 0.0022(4) 0.0050(4) 0.0036(4) C13 0.0258(6) 0.0220(6) 0.0201(6) 0.0043(5) 0.0048(5) 0.0039(5) C12 0.0265(6) 0.0214(6) 0.0203(6) 0.0002(5) 0.0023(5) 0.0027(5) C9 0.0264(6) 0.0236(6) 0.0184(6) 0.0019(5) 0.0040(5) 0.0077(5) C15 0.0268(6) 0.0178(5) 0.0238(6) 0.0008(4) 0.0066(5) 0.0052(5) C18 0.0238(6) 0.0212(5) 0.0193(6) 0.0024(4) 0.0038(4) 0.0067(4) C7 0.0260(6) 0.0259(6) 0.0204(6) 0.0035(5) 0.0054(5) 0.0081(5) C6 0.0248(6) 0.0212(6) 0.0216(6) 0.0001(5) 0.0035(5) 0.0043(5) C21 0.0211(5) 0.0198(5) 0.0176(5) 0.0002(4) 0.0000(4) 0.0054(4) C16 0.0291(6) 0.0224(6) 0.0229(6) 0.0051(5) 0.0104(5) 0.0066(5) C4 0.0302(6) 0.0203(6) 0.0200(6) 0.0038(5) 0.0023(5) 0.0064(5) C3 0.0333(7) 0.0205(6) 0.0210(6) -0.0003(5) -0.0015(5) 0.0083(5) O2 0.0430(6) 0.0279(5) 0.0218(5) 0.0022(4) -0.0011(4) 0.0070(4) O1 0.0346(5) 0.0248(5) 0.0258(5) 0.0049(4) 0.0051(4) 0.0096(4) _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 O28 C23 1.3590(14) . ? N17 C12 1.3364(15) . ? N17 C16 1.3365(15) . ? O29 C25 1.3771(13) . ? O27 C21 1.3590(13) . ? N8 C7 1.3384(16) . ? N8 C3 1.3391(16) . ? O20 C18 1.2357(14) . ? O11 C9 1.2390(15) . ? C22 C21 1.3921(16) . ? C22 C23 1.3952(15) . ? N19 C18 1.3303(16) . ? C24 C25 1.3909(16) . ? C24 C23 1.3956(15) . ? C5 C6 1.3876(17) . ? C5 C4 1.3901(16) . ? C5 C9 1.5085(15) . ? C25 C26 1.3900(16) . ? C26 C21 1.3929(15) . ? N10 C9 1.3284(16) . ? C14 C13 1.3857(16) . ? C14 C15 1.3890(17) . ? C14 C18 1.5089(15) . ? C13 C12 1.3872(17) . ? C15 C16 1.3906(17) . ? C7 C6 1.3914(16) . ? C4 C3 1.3842(17) . ? 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 N17 C16 117.29(10) . . ? C7 N8 C3 117.63(10) . . ? C21 C22 C23 119.41(10) . . ? C25 C24 C23 118.40(10) . . ? C6 C5 C4 118.10(11) . . ? C6 C5 C9 123.77(10) . . ? C4 C5 C9 118.13(11) . . ? O29 C25 C26 116.96(10) . . ? O29 C25 C24 120.99(10) . . ? C26 C25 C24 122.02(10) . . ? C25 C26 C21 118.52(10) . . ? C13 C14 C15 117.99(10) . . ? C13 C14 C18 118.45(10) . . ? C15 C14 C18 123.56(10) . . ? O28 C23 C22 121.37(10) . . ? O28 C23 C24 117.86(10) . . ? C22 C23 C24 120.76(10) . . ? C14 C13 C12 119.21(11) . . ? N17 C12 C13 123.26(11) . . ? O11 C9 N10 122.31(11) . . ? O11 C9 C5 119.34(10) . . ? N10 C9 C5 118.35(10) . . ? C14 C15 C16 118.85(11) . . ? O20 C18 N19 121.96(11) . . ? O20 C18 C14 119.88(10) . . ? N19 C18 C14 118.15(10) . . ? N8 C7 C6 122.91(11) . . ? C5 C6 C7 119.06(11) . . ? O27 C21 C22 121.64(10) . . ? O27 C21 C26 117.50(10) . . ? C22 C21 C26 120.86(10) . . ? N17 C16 C15 123.39(11) . . ? C3 C4 C5 119.04(11) . . ? N8 C3 C4 123.22(11) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.281 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.041 data_hqin _database_code_CSD 208485 _audit_creation_method SHELXL-97 _exptl_crystal_preparation Ethanol _chemical_name_systematic ; 1:2 molecular complex of hydroquinone and isonicotinamide ; _chemical_name_common '1:2 molecular complex of hydroquinone and isonicotinamide' _chemical_melting_point '428 K' _chemical_formula_moiety 'C6 H6 N2 O, 0.5(C6 H6 O2)' _chemical_formula_sum 'C9 H9 N2 O2' _chemical_formula_weight 177.18 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 14.2811(4) _cell_length_b 5.4136(2) _cell_length_c 11.9110(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.9340(10) _cell_angle_gamma 90.00 _cell_volume 854.21(5) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1933 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 27.47 _exptl_crystal_description Lathes _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal focus for the X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\w scans' _diffrn_standards_decay_% 'less than 1' _diffrn_reflns_number 3354 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0599 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1933 _reflns_number_gt 1277 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect data collection software, Nonius 1998' _computing_cell_refinement 'DENZO-SMN (Z. Otwinowski and W. Minor, 1997)' _computing_data_reduction 'SCALEPACK (Z. Otwinowski and W. Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTON (Spek, 1992)' _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^)+(0.0576P)^2^+0.0052P] 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 refall _refine_ls_extinction_method none _refine_ls_number_reflns 1933 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1131 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.73809(9) -0.1274(2) 0.67575(11) 0.0268(3) Uani 1 1 d . . . C2 C 0.83562(11) -0.1682(3) 0.69568(15) 0.0295(4) Uani 1 1 d . . . C3 C 0.89146(11) -0.3526(3) 0.77114(14) 0.0278(4) Uani 1 1 d . . . C4 C 0.84646(10) -0.5051(3) 0.83009(13) 0.0229(4) Uani 1 1 d . . . C5 C 0.74541(11) -0.4644(3) 0.80938(14) 0.0265(4) Uani 1 1 d . . . C6 C 0.69455(12) -0.2757(3) 0.73147(14) 0.0270(4) Uani 1 1 d . . . C7 C 0.90926(11) -0.7087(3) 0.90862(13) 0.0233(4) Uani 1 1 d . . . O8 O 0.99452(7) -0.7480(2) 0.90815(10) 0.0305(3) Uani 1 1 d . . . N9 N 0.87007(10) -0.8421(3) 0.97456(13) 0.0288(3) Uani 1 1 d . . . O1A O 0.66921(8) 0.2363(2) 0.51093(11) 0.0322(3) Uani 1 1 d . . . C1A C 0.58446(10) 0.3621(3) 0.50641(14) 0.0247(4) Uani 1 1 d . . . C2A C 0.52496(12) 0.2873(3) 0.56921(15) 0.0262(4) Uani 1 1 d . . . C3A C 0.44120(11) 0.4246(3) 0.56281(14) 0.0274(4) Uani 1 1 d . . . H5 H 0.7081(11) -0.563(3) 0.8490(14) 0.032(4) Uiso 1 1 d . . . H3 H 0.9623(11) -0.377(3) 0.7815(14) 0.029(4) Uiso 1 1 d . . . H6 H 0.6208(11) -0.248(3) 0.7149(13) 0.022(4) Uiso 1 1 d . . . H9B H 0.8069(14) -0.817(3) 0.9751(16) 0.040(5) Uiso 1 1 d . . . H2A H 0.5424(11) 0.140(3) 0.6173(15) 0.032(4) Uiso 1 1 d . . . H3A H 0.3965(11) 0.374(3) 0.6028(16) 0.037(4) Uiso 1 1 d . . . H2 H 0.8671(11) -0.060(3) 0.6526(15) 0.036(4) Uiso 1 1 d . . . H9A H 0.9124(14) -0.977(4) 1.0195(17) 0.056(6) Uiso 1 1 d . . . H1 H 0.6833(14) 0.112(4) 0.571(2) 0.060(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 N1 0.0264(7) 0.0257(7) 0.0286(7) 0.0010(6) 0.0106(6) 0.0030(6) C2 0.0274(8) 0.0287(9) 0.0339(9) 0.0061(7) 0.0133(8) 0.0010(7) C3 0.0229(8) 0.0276(9) 0.0337(9) 0.0037(7) 0.0115(7) 0.0017(7) C4 0.0249(8) 0.0220(8) 0.0219(8) -0.0020(6) 0.0087(6) 0.0018(6) C5 0.0259(8) 0.0290(9) 0.0265(9) 0.0029(7) 0.0120(7) 0.0004(7) C6 0.0239(8) 0.0300(9) 0.0281(9) 0.0023(7) 0.0110(7) 0.0035(7) C7 0.0241(8) 0.0222(8) 0.0239(8) -0.0009(6) 0.0092(6) 0.0010(6) O8 0.0259(6) 0.0311(7) 0.0373(7) 0.0083(5) 0.0152(5) 0.0084(5) N9 0.0287(7) 0.0273(8) 0.0339(8) 0.0075(6) 0.0157(6) 0.0046(7) O1A 0.0305(6) 0.0338(7) 0.0389(7) 0.0107(5) 0.0204(5) 0.0125(5) C1A 0.0230(7) 0.0251(8) 0.0272(9) -0.0010(7) 0.0109(7) 0.0025(7) C2A 0.0295(8) 0.0228(9) 0.0278(9) 0.0066(7) 0.0124(7) 0.0033(7) C3A 0.0278(8) 0.0297(9) 0.0292(9) 0.0035(7) 0.0156(7) -0.0007(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 N1 C6 1.334(2) . ? N1 C2 1.3408(19) . ? C2 C3 1.380(2) . ? C2 H2 0.991(17) . ? C3 C4 1.387(2) . ? C3 H3 0.982(15) . ? C4 C5 1.3878(19) . ? C4 C7 1.506(2) . ? C5 C6 1.389(2) . ? C5 H5 0.989(16) . ? C6 H6 1.007(14) . ? C7 O8 1.2381(17) . ? C7 N9 1.334(2) . ? N9 H9B 0.915(18) . ? N9 H9A 0.97(2) . ? O1A C1A 1.3723(18) . ? O1A H1 0.95(2) . ? C1A C2A 1.386(2) . ? C1A C3A 1.386(2) 3_666 ? C2A C3A 1.386(2) . ? C2A H2A 0.961(17) . ? C3A C1A 1.386(2) 3_666 ? C3A H3A 0.968(17) . ? 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 C6 N1 C2 117.35(13) . . ? N1 C2 C3 122.93(15) . . ? N1 C2 H2 117.0(9) . . ? C3 C2 H2 120.1(9) . . ? C2 C3 C4 119.71(13) . . ? C2 C3 H3 119.8(9) . . ? C4 C3 H3 120.4(9) . . ? C3 C4 C5 117.60(14) . . ? C3 C4 C7 117.96(13) . . ? C5 C4 C7 124.41(14) . . ? C4 C5 C6 119.01(15) . . ? C4 C5 H5 122.6(9) . . ? C6 C5 H5 118.4(9) . . ? N1 C6 C5 123.39(14) . . ? N1 C6 H6 117.5(9) . . ? C5 C6 H6 119.1(9) . . ? O8 C7 N9 122.63(14) . . ? O8 C7 C4 118.78(13) . . ? N9 C7 C4 118.57(13) . . ? C7 N9 H9B 123.8(11) . . ? C7 N9 H9A 114.8(11) . . ? H9B N9 H9A 121.3(16) . . ? C1A O1A H1 108.4(12) . . ? O1A C1A C2A 122.92(14) . . ? O1A C1A C3A 118.04(14) . 3_666 ? C2A C1A C3A 119.04(14) . 3_666 ? C1A C2A C3A 120.28(15) . . ? C1A C2A H2A 119.4(9) . . ? C3A C2A H2A 120.3(9) . . ? C2A C3A C1A 120.69(15) . 3_666 ? C2A C3A H3A 122.3(10) . . ? C1A C3A H3A 116.9(10) 3_666 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 C3 -0.6(2) . . . . ? N1 C2 C3 C4 0.0(3) . . . . ? C2 C3 C4 C5 0.3(2) . . . . ? C2 C3 C4 C7 178.20(14) . . . . ? C3 C4 C5 C6 0.1(2) . . . . ? C7 C4 C5 C6 -177.66(14) . . . . ? C2 N1 C6 C5 1.1(2) . . . . ? C4 C5 C6 N1 -0.8(2) . . . . ? C3 C4 C7 O8 -7.1(2) . . . . ? C5 C4 C7 O8 170.64(14) . . . . ? C3 C4 C7 N9 173.89(14) . . . . ? C5 C4 C7 N9 -8.4(2) . . . . ? O1A C1A C2A C3A 178.83(14) . . . . ? C3A C1A C2A C3A -0.1(3) 3_666 . . . ? C1A C2A C3A C1A 0.1(3) . . . 3_666 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.183 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.047