# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Urbanczyk-Lipkowska, Z.' 'Szczesna, B.' _publ_contact_author_name 'Dr Z Urbanczyk-Lipkowska' _publ_contact_author_address ; Institute of Organic Chemistry Polish Academy of Sciences Kasprzaka Str. 44/52 Warsaw 01-224 POLAND ; _publ_contact_author_email 'OCRYST@ICHO.EDU.PL' _publ_section_title ; Cooperative effect of multiple hydrogen bonding involving nitro group - solid state dimeric self-assembly of o-, m-, p-hydroxyphenyl-2,4-dinitrophenylhydrazones ; data_compound_1 _database_code_CSD 177492 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-[(2,4-Dinitro-phenyl)-hydrazonomethyl]-phenol ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 N4 O5' _chemical_formula_weight 302.25 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.7670(4) _cell_length_b 4.3530(1) _cell_length_c 21.1180(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.4070(12) _cell_angle_gamma 90.00 _cell_volume 1265.52(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 2935 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.878 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'KappaCCD' _diffrn_measurement_method '181.5°phi, 36.0°omega, 91.5°omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5574 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0631 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.88 _reflns_number_total 2973 _reflns_number_gt 1886 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0070(16) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2973 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1049 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1065 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O5 O 0.23874(10) -0.8297(3) 0.18071(5) 0.0300(3) Uani 1 d . . . H5 H 0.2860(18) -0.689(5) 0.1790(11) 0.068(8) Uiso 1 d . . . O4 O 0.61380(9) 0.0874(3) 0.37671(6) 0.0386(4) Uani 1 d . . . O3 O 0.70349(10) 0.3753(3) 0.31787(6) 0.0436(4) Uani 1 d . . . O2 O 0.65633(9) 0.4045(3) 0.09726(5) 0.0327(3) Uani 1 d . . . O1 O 0.55388(9) 0.1104(2) 0.04801(5) 0.0303(3) Uani 1 d . . . N4 N 0.63815(10) 0.1873(3) 0.32500(7) 0.0255(4) Uani 1 d . . . N3 N 0.59343(10) 0.2049(3) 0.09761(7) 0.0220(3) Uani 1 d . . . N2 N 0.43869(10) -0.2556(3) 0.11095(7) 0.0204(3) Uani 1 d . . . H2 H 0.4543(14) -0.196(4) 0.0718(10) 0.044(6) Uiso 1 d . . . N1 N 0.36589(9) -0.4709(3) 0.11878(6) 0.0191(3) Uani 1 d . . . C7 C 0.32792(12) -0.5724(3) 0.06680(8) 0.0194(4) Uani 1 d . . . H7 H 0.3534(11) -0.500(3) 0.0269(8) 0.019(4) Uiso 1 d . . . C11 C 0.25001(11) -0.7954(3) 0.06643(8) 0.0180(4) Uani 1 d . . . C12 C 0.20758(12) -0.9117(3) 0.12179(8) 0.0214(4) Uani 1 d . . . C13 C 0.13120(13) -1.1197(4) 0.11751(9) 0.0261(4) Uani 1 d . . . H13 H 0.1029(13) -1.196(4) 0.1562(9) 0.035(5) Uiso 1 d . . . C14 C 0.09601(14) -1.2099(4) 0.05900(9) 0.0296(5) Uani 1 d . . . H14 H 0.0446(13) -1.347(4) 0.0551(8) 0.033(5) Uiso 1 d . . . C15 C 0.13651(13) -1.0965(4) 0.00387(9) 0.0281(4) Uani 1 d . . . H15 H 0.1145(13) -1.153(4) -0.0352(9) 0.036(5) Uiso 1 d . . . C16 C 0.21237(13) -0.8912(3) 0.00753(8) 0.0232(4) Uani 1 d . . . H16 H 0.2400(11) -0.807(3) -0.0288(8) 0.019(4) Uiso 1 d . . . C1 C 0.48520(12) -0.1359(3) 0.16208(7) 0.0183(4) Uani 1 d . . . C6 C 0.45849(13) -0.2256(4) 0.22422(8) 0.0220(4) Uani 1 d . . . H6 H 0.4051(13) -0.354(3) 0.2282(7) 0.021(4) Uiso 1 d . . . C5 C 0.50801(12) -0.1240(4) 0.27626(8) 0.0214(4) Uani 1 d . . . H5' H 0.4895(13) -0.186(4) 0.3165(9) 0.029(5) Uiso 1 d . . . C4 C 0.58505(12) 0.0788(3) 0.26915(7) 0.0195(4) Uani 1 d . . . C3 C 0.61190(12) 0.1847(4) 0.21076(8) 0.0198(4) Uani 1 d . . . H3 H 0.6626(13) 0.327(4) 0.2058(8) 0.028(5) Uiso 1 d . . . C2 C 0.56219(12) 0.0798(3) 0.15756(7) 0.0182(4) Uani 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 O5 0.0365(8) 0.0328(7) 0.0208(7) -0.0006(5) 0.0047(6) -0.0101(6) O4 0.0414(9) 0.0566(8) 0.0177(7) 0.0021(6) -0.0005(6) -0.0087(6) O3 0.0412(9) 0.0567(8) 0.0329(8) 0.0021(6) -0.0054(6) -0.0265(7) O2 0.0338(8) 0.0368(7) 0.0277(7) 0.0040(5) 0.0028(6) -0.0192(6) O1 0.0329(8) 0.0401(7) 0.0179(6) 0.0013(5) -0.0007(5) -0.0123(6) N4 0.0242(9) 0.0317(8) 0.0207(8) -0.0016(6) -0.0006(7) 0.0002(7) N3 0.0217(8) 0.0257(7) 0.0187(8) 0.0021(6) 0.0011(6) -0.0027(6) N2 0.0198(8) 0.0214(7) 0.0199(8) 0.0014(6) 0.0021(6) -0.0051(6) N1 0.0185(8) 0.0166(6) 0.0221(7) 0.0006(6) 0.0009(6) -0.0002(6) C7 0.0201(10) 0.0194(8) 0.0185(9) 0.0028(7) 0.0032(7) 0.0016(7) C11 0.0155(9) 0.0162(8) 0.0223(9) 0.0008(7) 0.0006(7) 0.0025(6) C12 0.0216(10) 0.0208(8) 0.0220(9) -0.0007(7) 0.0037(7) 0.0034(7) C13 0.0242(11) 0.0213(9) 0.0331(11) 0.0010(8) 0.0102(9) -0.0010(7) C14 0.0208(10) 0.0221(9) 0.0460(13) -0.0061(8) 0.0012(9) -0.0023(8) C15 0.0282(11) 0.0262(9) 0.0296(11) -0.0062(8) -0.0054(9) -0.0006(8) C16 0.0250(10) 0.0217(9) 0.0230(10) 0.0020(7) -0.0004(8) 0.0022(7) C1 0.0195(10) 0.0166(8) 0.0189(9) -0.0011(7) 0.0016(7) 0.0039(6) C6 0.0203(10) 0.0209(8) 0.0248(10) -0.0009(7) 0.0034(8) -0.0031(8) C5 0.0253(11) 0.0227(9) 0.0163(9) 0.0021(7) 0.0038(8) 0.0029(7) C4 0.0184(9) 0.0227(8) 0.0175(9) -0.0012(7) -0.0014(7) 0.0036(7) C3 0.0157(9) 0.0206(8) 0.0233(9) -0.0006(7) 0.0021(7) 0.0012(7) C2 0.0195(9) 0.0184(8) 0.0168(8) 0.0022(6) 0.0031(7) 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 O5 C12 1.3609(19) . ? O5 H5 0.90(2) . ? O4 N4 1.2245(17) . ? O3 N4 1.2261(17) . ? O2 N3 1.2267(16) . ? O1 N3 1.2469(17) . ? N4 C4 1.462(2) . ? N3 C2 1.446(2) . ? N2 C1 1.355(2) . ? N2 N1 1.3831(18) . ? N2 H2 0.89(2) . ? N1 C7 1.2905(19) . ? C7 C11 1.447(2) . ? C7 H7 0.968(17) . ? C11 C12 1.405(2) . ? C11 C16 1.407(2) . ? C12 C13 1.390(2) . ? C13 C14 1.381(2) . ? C13 H13 0.967(19) . ? C14 C15 1.385(3) . ? C14 H14 0.930(18) . ? C15 C16 1.376(2) . ? C15 H15 0.910(17) . ? C16 H16 0.934(17) . ? C1 C2 1.420(2) . ? C1 C6 1.420(2) . ? C6 C5 1.363(2) . ? C6 H6 0.928(17) . ? C5 C4 1.389(2) . ? C5 H5 0.928(18) . ? C4 C3 1.370(2) . ? C3 C2 1.388(2) . ? C3 H3 0.939(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 O5 H5 111.6(15) . . ? O4 N4 O3 123.52(14) . . ? O4 N4 C4 117.80(14) . . ? O3 N4 C4 118.67(14) . . ? O2 N3 O1 122.18(13) . . ? O2 N3 C2 119.10(13) . . ? O1 N3 C2 118.70(13) . . ? C1 N2 N1 120.25(14) . . ? C1 N2 H2 120.6(12) . . ? N1 N2 H2 119.1(12) . . ? C7 N1 N2 114.82(13) . . ? N1 C7 C11 122.01(15) . . ? N1 C7 H7 118.8(9) . . ? C11 C7 H7 119.2(9) . . ? C12 C11 C16 118.44(15) . . ? C12 C11 C7 123.36(14) . . ? C16 C11 C7 118.16(15) . . ? O5 C12 C13 117.62(15) . . ? O5 C12 C11 122.43(14) . . ? C13 C12 C11 119.95(15) . . ? C14 C13 C12 120.25(17) . . ? C14 C13 H13 121.1(10) . . ? C12 C13 H13 118.6(10) . . ? C13 C14 C15 120.67(17) . . ? C13 C14 H14 121.7(11) . . ? C15 C14 H14 117.7(11) . . ? C16 C15 C14 119.58(17) . . ? C16 C15 H15 118.3(12) . . ? C14 C15 H15 122.1(11) . . ? C15 C16 C11 121.11(17) . . ? C15 C16 H16 121.4(10) . . ? C11 C16 H16 117.4(10) . . ? N2 C1 C2 123.31(14) . . ? N2 C1 C6 120.43(15) . . ? C2 C1 C6 116.25(14) . . ? C5 C6 C1 121.64(16) . . ? C5 C6 H6 121.0(10) . . ? C1 C6 H6 117.3(10) . . ? C6 C5 C4 119.80(16) . . ? C6 C5 H5 120.3(11) . . ? C4 C5 H5 119.9(11) . . ? C3 C4 C5 121.49(14) . . ? C3 C4 N4 118.76(14) . . ? C5 C4 N4 119.74(14) . . ? C4 C3 C2 118.89(15) . . ? C4 C3 H3 121.8(10) . . ? C2 C3 H3 119.3(10) . . ? C3 C2 C1 121.80(15) . . ? C3 C2 N3 115.87(14) . . ? C1 C2 N3 122.33(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 C1 N2 N1 C7 -178.90(13) . . . . ? N2 N1 C7 C11 -179.15(12) . . . . ? N1 C7 C11 C12 2.0(2) . . . . ? N1 C7 C11 C16 179.44(14) . . . . ? C16 C11 C12 O5 -179.45(14) . . . . ? C7 C11 C12 O5 -2.1(2) . . . . ? C16 C11 C12 C13 0.9(2) . . . . ? C7 C11 C12 C13 178.31(14) . . . . ? O5 C12 C13 C14 179.56(15) . . . . ? C11 C12 C13 C14 -0.8(2) . . . . ? C12 C13 C14 C15 0.4(3) . . . . ? C13 C14 C15 C16 -0.2(3) . . . . ? C14 C15 C16 C11 0.4(3) . . . . ? C12 C11 C16 C15 -0.7(2) . . . . ? C7 C11 C16 C15 -178.25(14) . . . . ? N1 N2 C1 C2 178.33(12) . . . . ? N1 N2 C1 C6 -1.2(2) . . . . ? N2 C1 C6 C5 175.78(15) . . . . ? C2 C1 C6 C5 -3.8(2) . . . . ? C1 C6 C5 C4 1.7(2) . . . . ? C6 C5 C4 C3 1.1(2) . . . . ? C6 C5 C4 N4 -179.93(14) . . . . ? O4 N4 C4 C3 -179.18(14) . . . . ? O3 N4 C4 C3 1.7(2) . . . . ? O4 N4 C4 C5 1.8(2) . . . . ? O3 N4 C4 C5 -177.24(14) . . . . ? C5 C4 C3 C2 -1.7(2) . . . . ? N4 C4 C3 C2 179.39(13) . . . . ? C4 C3 C2 C1 -0.6(2) . . . . ? C4 C3 C2 N3 179.05(13) . . . . ? N2 C1 C2 C3 -176.31(14) . . . . ? C6 C1 C2 C3 3.3(2) . . . . ? N2 C1 C2 N3 4.0(2) . . . . ? C6 C1 C2 N3 -176.41(13) . . . . ? O2 N3 C2 C3 -4.2(2) . . . . ? O1 N3 C2 C3 177.34(13) . . . . ? O2 N3 C2 C1 175.54(13) . . . . ? O1 N3 C2 C1 -3.0(2) . . . . ? 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 N2 H2 O1 0.89(2) 2.56(2) 3.4182(19) 161.3(17) 3_655 _diffrn_measured_fraction_theta_max 0.872 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.872 _refine_diff_density_max 0.232 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.052 #===END data_compound_2 _database_code_CSD 177493 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-[(2,4-Dinitro-phenyl)-hydrazonomethyl]-phenol ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 N4 O5' _chemical_formula_weight 302.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7902(10) _cell_length_b 14.0346(10) _cell_length_c 9.8226(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.32(3) _cell_angle_gamma 90.00(10) _cell_volume 1323.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 18.54 _cell_measurement_theta_max 42.88 _exptl_crystal_description ? _exptl_crystal_colour red _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 1.024 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Mach3 _diffrn_measurement_method omega\2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 3000 _diffrn_standards_decay_% 1 _diffrn_reflns_number 2913 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 5.57 _diffrn_reflns_theta_max 73.01 _reflns_number_total 1611 _reflns_number_gt 1521 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Express, Nonius BV' _computing_cell_refinement 'Express, Nonius BV' _computing_data_reduction 'OpenMolen 2.2' _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 w=1/[\s^2^(Fo^2^)+(0.0749P)^2^+0.0559P] 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 SHELXL _refine_ls_extinction_coef 0.0007(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1611 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1372 _refine_ls_wR_factor_gt 0.1337 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.150 _refine_ls_shift/su_max 0.106 _refine_ls_shift/su_mean 0.007 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9635(3) 0.2646(2) 0.9874(3) 0.0497(7) Uani 1 d . . . C2 C 0.8274(3) 0.2928(2) 0.9241(3) 0.0493(7) Uani 1 d . . . C3 C 0.7192(3) 0.2279(2) 0.8928(3) 0.0541(8) Uani 1 d . . . H3 H 0.6307 0.2477 0.8493 0.065 Uiso 1 calc R . . C4 C 0.7445(3) 0.1343(2) 0.9270(4) 0.0552(8) Uani 1 d . . . C5 C 0.8754(3) 0.1041(2) 0.9944(4) 0.0645(9) Uani 1 d . . . H5 H 0.8899 0.0406 1.0198 0.077 Uiso 1 calc R . . C6 C 0.9826(3) 0.1673(2) 1.0233(4) 0.0611(9) Uani 1 d . . . H6 H 1.0701 0.1460 1.0675 0.073 Uiso 1 calc R . . C7 C 1.3030(3) 0.3500(3) 1.0739(4) 0.0591(9) Uani 1 d . . . H7 H 1.285(4) 0.410(3) 1.042(4) 0.077(12) Uiso 1 d . . . C8 C 1.4462(3) 0.3210(2) 1.1278(4) 0.0568(8) Uani 1 d . . . C9 C 1.4807(3) 0.2250(2) 1.1468(3) 0.0565(8) Uani 1 d . . . H9 H 1.4125 0.1788 1.1209 0.068 Uiso 1 calc R . . C10 C 1.6142(3) 0.1982(2) 1.2033(4) 0.0604(9) Uani 1 d . . . C11 C 1.7164(3) 0.2659(3) 1.2416(4) 0.0655(9) Uani 1 d . . . H11 H 1.8069 0.2475 1.2806 0.079 Uiso 1 calc R . . C12 C 1.6837(4) 0.3613(3) 1.2217(4) 0.0739(11) Uani 1 d . . . H12 H 1.7527 0.4070 1.2472 0.089 Uiso 1 calc R . . C13 C 1.5496(4) 0.3895(3) 1.1642(4) 0.0693(10) Uani 1 d . . . H13 H 1.5286 0.4538 1.1500 0.083 Uiso 1 calc R . . N1 N 1.2035(2) 0.29020(19) 1.0653(3) 0.0550(7) Uani 1 d . . . N2 N 1.0734(3) 0.3250(2) 1.0142(3) 0.0566(7) Uani 1 d . . . H2 H 1.051(4) 0.382(3) 0.999(4) 0.079(13) Uiso 1 d . . . N3 N 0.7937(3) 0.39045(19) 0.8848(3) 0.0631(8) Uani 1 d . . . N4 N 0.6317(3) 0.0663(2) 0.8913(4) 0.0727(9) Uani 1 d . . . O1 O 0.8860(3) 0.45089(16) 0.9096(3) 0.0870(9) Uani 1 d . . . O2 O 0.6751(3) 0.40999(17) 0.8279(3) 0.0872(9) Uani 1 d . . . O3 O 0.5197(3) 0.0935(2) 0.8281(4) 0.0995(10) Uani 1 d . . . O4 O 0.6544(3) -0.0162(2) 0.9270(4) 0.1044(11) Uani 1 d . . . O5 O 1.6513(3) 0.1031(2) 1.2251(3) 0.0802(8) Uani 1 d . . . H5A H 1.574(6) 0.074(4) 1.190(6) 0.13(2) Uiso 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 0.0477(16) 0.0474(17) 0.0523(19) -0.0022(14) 0.0059(13) -0.0043(13) C2 0.0474(16) 0.0418(16) 0.0564(19) -0.0021(14) 0.0047(13) -0.0028(13) C3 0.0391(15) 0.061(2) 0.061(2) -0.0061(16) 0.0076(13) -0.0044(14) C4 0.0523(17) 0.0476(19) 0.067(2) -0.0098(16) 0.0161(15) -0.0105(14) C5 0.0589(19) 0.0437(17) 0.092(3) 0.0029(18) 0.0182(17) -0.0019(15) C6 0.0495(18) 0.053(2) 0.078(3) 0.0065(17) 0.0052(16) 0.0032(15) C7 0.0550(18) 0.0522(19) 0.067(2) -0.0031(18) 0.0049(15) -0.0054(16) C8 0.0461(17) 0.059(2) 0.063(2) -0.0067(16) 0.0049(14) -0.0105(14) C9 0.0456(16) 0.0563(19) 0.067(2) -0.0095(17) 0.0099(14) -0.0125(14) C10 0.0551(18) 0.063(2) 0.065(2) -0.0076(17) 0.0159(15) -0.0034(16) C11 0.0415(17) 0.080(2) 0.074(2) -0.005(2) 0.0087(15) -0.0047(16) C12 0.0539(19) 0.078(3) 0.087(3) -0.013(2) 0.0052(17) -0.0262(18) C13 0.0569(19) 0.060(2) 0.089(3) -0.0079(19) 0.0091(18) -0.0140(16) N1 0.0442(14) 0.0568(15) 0.0602(17) -0.0015(13) 0.0009(11) -0.0073(12) N2 0.0437(14) 0.0490(17) 0.071(2) -0.0024(14) -0.0023(12) -0.0057(11) N3 0.0565(16) 0.0477(15) 0.078(2) -0.0031(14) -0.0030(14) -0.0002(13) N4 0.0640(19) 0.063(2) 0.095(2) -0.0230(18) 0.0234(17) -0.0224(15) O1 0.0653(15) 0.0456(13) 0.138(3) 0.0053(15) -0.0086(15) -0.0096(12) O2 0.0631(15) 0.0604(16) 0.124(2) -0.0015(15) -0.0168(15) 0.0093(12) O3 0.0517(15) 0.098(2) 0.144(3) -0.026(2) 0.0069(16) -0.0244(15) O4 0.110(2) 0.0513(16) 0.151(3) -0.0118(18) 0.025(2) -0.0315(15) O5 0.0657(16) 0.0621(16) 0.112(2) -0.0040(16) 0.0153(15) 0.0008(13) _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 N2 1.354(4) . ? C1 C6 1.414(4) . ? C1 C2 1.412(4) . ? C2 C3 1.385(4) . ? C2 N3 1.445(4) . ? C3 C4 1.367(4) . ? C3 H3 0.9300 . ? C4 C5 1.388(5) . ? C4 N4 1.449(4) . ? C5 C6 1.361(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.276(4) . ? C7 C8 1.456(5) . ? C7 H7 0.90(4) . ? C8 C9 1.392(4) . ? C8 C13 1.391(4) . ? C9 C10 1.369(4) . ? C9 H9 0.9300 . ? C10 C11 1.377(5) . ? C10 O5 1.388(4) . ? C11 C12 1.382(5) . ? C11 H11 0.9300 . ? C12 C13 1.381(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? N1 N2 1.364(4) . ? N2 H2 0.83(4) . ? N3 O2 1.217(3) . ? N3 O1 1.229(3) . ? N4 O3 1.210(4) . ? N4 O4 1.218(4) . ? O5 H5A 0.87(6) . ? 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 N2 C1 C6 119.6(3) . . ? N2 C1 C2 123.8(3) . . ? C6 C1 C2 116.6(3) . . ? C3 C2 C1 121.9(3) . . ? C3 C2 N3 116.1(3) . . ? C1 C2 N3 122.0(3) . . ? C4 C3 C2 118.9(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 121.1(3) . . ? C3 C4 N4 118.7(3) . . ? C5 C4 N4 120.2(3) . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 121.2(3) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? N1 C7 C8 120.6(3) . . ? N1 C7 H7 120(2) . . ? C8 C7 H7 120(2) . . ? C9 C8 C13 119.3(3) . . ? C9 C8 C7 120.7(3) . . ? C13 C8 C7 120.0(3) . . ? C10 C9 C8 120.5(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 120.3(3) . . ? C9 C10 O5 121.8(3) . . ? C11 C10 O5 117.8(3) . . ? C12 C11 C10 119.6(3) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 120.7(3) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C12 C13 C8 119.5(4) . . ? C12 C13 H13 120.2 . . ? C8 C13 H13 120.3 . . ? C7 N1 N2 115.8(3) . . ? C1 N2 N1 119.8(3) . . ? C1 N2 H2 113(3) . . ? N1 N2 H2 127(3) . . ? O2 N3 O1 122.3(3) . . ? O2 N3 C2 119.0(3) . . ? O1 N3 C2 118.8(3) . . ? O3 N4 O4 122.9(3) . . ? O3 N4 C4 119.2(3) . . ? O4 N4 C4 117.9(3) . . ? C10 O5 H5A 102(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C1 C2 C3 177.1(3) . . . . ? C6 C1 C2 C3 -2.8(5) . . . . ? N2 C1 C2 N3 -1.3(5) . . . . ? C6 C1 C2 N3 178.8(3) . . . . ? C1 C2 C3 C4 1.4(5) . . . . ? N3 C2 C3 C4 179.8(3) . . . . ? C2 C3 C4 C5 1.3(5) . . . . ? C2 C3 C4 N4 -178.7(3) . . . . ? C3 C4 C5 C6 -2.3(6) . . . . ? N4 C4 C5 C6 177.6(3) . . . . ? C4 C5 C6 C1 0.8(6) . . . . ? N2 C1 C6 C5 -178.2(3) . . . . ? C2 C1 C6 C5 1.8(5) . . . . ? N1 C7 C8 C9 12.0(6) . . . . ? N1 C7 C8 C13 -166.4(3) . . . . ? C13 C8 C9 C10 1.3(6) . . . . ? C7 C8 C9 C10 -177.1(3) . . . . ? C8 C9 C10 C11 -0.3(6) . . . . ? C8 C9 C10 O5 179.2(3) . . . . ? C9 C10 C11 C12 -0.5(6) . . . . ? O5 C10 C11 C12 -179.9(4) . . . . ? C10 C11 C12 C13 0.2(6) . . . . ? C11 C12 C13 C8 0.8(6) . . . . ? C9 C8 C13 C12 -1.6(6) . . . . ? C7 C8 C13 C12 176.8(4) . . . . ? C8 C7 N1 N2 179.6(3) . . . . ? C6 C1 N2 N1 5.2(5) . . . . ? C2 C1 N2 N1 -174.7(3) . . . . ? C7 N1 N2 C1 172.8(3) . . . . ? C3 C2 N3 O2 0.0(5) . . . . ? C1 C2 N3 O2 178.4(3) . . . . ? C3 C2 N3 O1 -179.7(3) . . . . ? C1 C2 N3 O1 -1.3(5) . . . . ? C3 C4 N4 O3 2.6(5) . . . . ? C5 C4 N4 O3 -177.4(4) . . . . ? C3 C4 N4 O4 -177.3(4) . . . . ? C5 C4 N4 O4 2.7(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 N2 H2 O1 0.83(4) 1.94(4) 2.609(4) 136(4) . N2 H2 O1 0.83(4) 2.55(4) 3.240(4) 142(3) 3_767 O5 H5A O4 0.87(6) 2.44(6) 3.305(5) 171(5) 3_757 O5 H5A O3 0.87(6) 2.52(6) 3.216(5) 138(5) 3_757 C7 H7 O2 0.90(4) 2.83(4) 3.499(4) 133(3) 3_767 C7 H7 O1 0.90(4) 2.68(4) 3.374(5) 135(3) 3_767 C13 H13 O2 0.93 2.80 3.583(5) 142.2 3_767 _diffrn_measured_fraction_theta_max 0.584 _diffrn_reflns_theta_full 73.01 _diffrn_measured_fraction_theta_full 0.584 _refine_diff_density_max 0.355 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.043 #===END data_compound_3 _database_code_CSD 177494 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-[(2,4-Dinitro-phenyl)-hydrazonomethyl]-phenol ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 N4 O5' _chemical_formula_weight 302.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.4297(4) _cell_length_b 6.1857(7) _cell_length_c 24.7150(14) _cell_angle_alpha 90.00 _cell_angle_beta 91.488(11) _cell_angle_gamma 90.00 _cell_volume 1288.29(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15 _cell_measurement_theta_min 23.2 _cell_measurement_theta_max 42.2 _exptl_crystal_description ? _exptl_crystal_colour red _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 1.052 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 94.96 _exptl_absorpt_correction_T_max 99.99 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Mach3 _diffrn_measurement_method omega/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 3000 s _diffrn_standards_decay_% 1 _diffrn_reflns_number 2665 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 73.95 _reflns_number_total 2606 _reflns_number_gt 1830 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Express, Nonius BV' _computing_cell_refinement 'Express, Nonius BV' _computing_data_reduction 'OpenMolen 2.2' _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 w=1/[\s^2^(Fo^2^)+(0.0569P)^2^+0.6760P] 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 SHELXL _refine_ls_extinction_coef 0.0154(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2606 _refine_ls_number_parameters 212 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0895 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1570 _refine_ls_wR_factor_gt 0.1333 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.126 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7690(3) 0.7435(4) 0.09023(10) 0.0347(6) Uani 1 d . . . C2 C 0.7299(3) 0.5494(4) 0.11750(10) 0.0336(5) Uani 1 d . . . C3 C 0.7976(3) 0.4994(4) 0.16790(10) 0.0386(6) Uani 1 d . . . H3 H 0.7725 0.3707 0.1851 0.046 Uiso 1 calc R . . C4 C 0.9016(3) 0.6424(5) 0.19169(10) 0.0412(6) Uani 1 d . . . C5 C 0.9411(3) 0.8359(5) 0.16672(11) 0.0442(7) Uani 1 d . . . H5 H 1.0123 0.9306 0.1836 0.053 Uiso 1 calc R . . C6 C 0.8750(3) 0.8862(4) 0.11749(10) 0.0416(6) Uani 1 d . . . H6 H 0.9002 1.0172 0.1014 0.050 Uiso 1 calc R . . C7 C 0.6951(3) 1.0128(4) -0.03175(10) 0.0388(6) Uani 1 d . . . H7 H 0.626(3) 0.901(4) -0.0483(10) 0.036(7) Uiso 1 d . . . C8 C 0.7313(3) 1.2020(4) -0.06396(9) 0.0336(5) Uani 1 d . . . C13 C 0.6587(3) 1.2232(4) -0.11539(10) 0.0366(6) Uani 1 d . . . H13 H 0.5912 1.1149 -0.1283 0.044 Uiso 1 calc R . . C12 C 0.6859(3) 1.4016(4) -0.14712(10) 0.0379(6) Uani 1 d . . . H12 H 0.6377 1.4124 -0.1813 0.045 Uiso 1 calc R . . C11 C 0.7848(3) 1.5646(4) -0.12825(10) 0.0370(6) Uani 1 d . . . C10 C 0.8602(3) 1.5456(4) -0.07751(10) 0.0398(6) Uani 1 d . . . H10 H 0.9284 1.6538 -0.0650 0.048 Uiso 1 calc R . . C9 C 0.8336(3) 1.3669(4) -0.04609(10) 0.0378(6) Uani 1 d . . . H9 H 0.8844 1.3552 -0.0124 0.045 Uiso 1 calc R . . N1 N 0.7579(3) 0.9844(3) 0.01585(8) 0.0392(5) Uani 1 d . . . N2 N 0.7097(3) 0.7948(3) 0.04030(8) 0.0392(5) Uani 1 d D . . H2 H 0.640(3) 0.688(4) 0.0200(10) 0.055(9) Uiso 1 d D . . N3 N 0.6228(2) 0.3908(3) 0.09448(8) 0.0373(5) Uani 1 d . . . N4 N 0.9798(3) 0.5837(5) 0.24286(10) 0.0553(7) Uani 1 d . . . O1 O 0.5644(2) 0.4233(3) 0.04866(7) 0.0463(5) Uani 1 d . . . O2 O 0.5910(2) 0.2298(3) 0.12101(8) 0.0528(6) Uani 1 d . . . O3 O 1.0823(3) 0.7083(5) 0.26058(9) 0.0818(9) Uani 1 d . . . O4 O 0.9422(3) 0.4168(5) 0.26549(10) 0.0831(9) Uani 1 d . . . O5 O 0.8155(3) 1.7464(3) -0.15712(8) 0.0529(6) Uani 1 d D . . H5A H 0.734(3) 1.771(7) -0.1855(11) 0.104(14) Uiso 1 d 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 0.0359(13) 0.0330(13) 0.0351(12) 0.0010(10) -0.0021(10) 0.0023(10) C2 0.0314(12) 0.0332(13) 0.0358(12) 0.0002(10) -0.0061(10) -0.0005(10) C3 0.0391(14) 0.0412(15) 0.0353(13) 0.0042(11) -0.0026(10) -0.0003(11) C4 0.0429(14) 0.0481(15) 0.0321(12) 0.0003(11) -0.0090(11) 0.0024(12) C5 0.0404(14) 0.0456(16) 0.0463(15) -0.0060(12) -0.0070(11) -0.0052(12) C6 0.0485(15) 0.0329(13) 0.0433(14) 0.0018(11) -0.0039(11) -0.0048(12) C7 0.0420(14) 0.0360(14) 0.0380(13) 0.0009(11) -0.0046(11) -0.0004(11) C8 0.0362(12) 0.0337(13) 0.0307(11) 0.0018(10) -0.0031(9) 0.0024(10) C13 0.0375(13) 0.0360(13) 0.0357(13) -0.0022(11) -0.0079(10) -0.0034(11) C12 0.0397(13) 0.0413(14) 0.0321(12) 0.0025(11) -0.0112(10) -0.0001(11) C11 0.0393(13) 0.0346(13) 0.0367(13) 0.0056(10) -0.0041(10) 0.0019(11) C10 0.0396(13) 0.0386(14) 0.0406(14) -0.0001(11) -0.0109(11) -0.0075(11) C9 0.0416(13) 0.0407(14) 0.0305(12) 0.0026(11) -0.0104(10) -0.0022(11) N1 0.0462(12) 0.0336(11) 0.0376(11) 0.0067(9) -0.0055(9) -0.0027(9) N2 0.0491(13) 0.0320(11) 0.0360(11) 0.0071(9) -0.0088(9) -0.0055(10) N3 0.0395(11) 0.0336(11) 0.0384(11) 0.0040(9) -0.0059(9) -0.0008(9) N4 0.0592(16) 0.0706(18) 0.0355(12) 0.0005(13) -0.0132(11) 0.0007(14) O1 0.0534(11) 0.0449(11) 0.0397(10) 0.0021(8) -0.0156(8) -0.0093(9) O2 0.0612(13) 0.0403(11) 0.0560(12) 0.0135(9) -0.0127(10) -0.0140(9) O3 0.0886(18) 0.101(2) 0.0543(14) -0.0033(14) -0.0354(13) -0.0235(16) O4 0.104(2) 0.088(2) 0.0549(14) 0.0268(14) -0.0280(13) -0.0132(17) O5 0.0590(13) 0.0448(11) 0.0540(12) 0.0164(10) -0.0173(10) -0.0097(10) _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 N2 1.357(3) . ? C1 C6 1.415(3) . ? C1 C2 1.420(3) . ? C2 C3 1.391(3) . ? C2 N3 1.441(3) . ? C3 C4 1.367(4) . ? C4 C5 1.392(4) . ? C4 N4 1.457(3) . ? C5 C6 1.361(4) . ? C7 N1 1.289(3) . ? C7 C8 1.452(3) . ? C8 C9 1.401(3) . ? C8 C13 1.402(3) . ? C13 C12 1.377(3) . ? C12 C11 1.382(3) . ? C11 O5 1.360(3) . ? C11 C10 1.396(3) . ? C10 C9 1.372(3) . ? N1 N2 1.385(3) . ? N3 O2 1.226(3) . ? N3 O1 1.239(3) . ? N4 O4 1.220(3) . ? N4 O3 1.230(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 C6 120.1(2) . . ? N2 C1 C2 123.0(2) . . ? C6 C1 C2 116.9(2) . . ? C3 C2 C1 121.2(2) . . ? C3 C2 N3 116.1(2) . . ? C1 C2 N3 122.6(2) . . ? C4 C3 C2 119.0(2) . . ? C3 C4 C5 121.6(2) . . ? C3 C4 N4 118.9(3) . . ? C5 C4 N4 119.4(3) . . ? C6 C5 C4 119.7(3) . . ? C5 C6 C1 121.5(3) . . ? N1 C7 C8 121.5(2) . . ? C9 C8 C13 117.9(2) . . ? C9 C8 C7 123.4(2) . . ? C13 C8 C7 118.6(2) . . ? C12 C13 C8 121.1(2) . . ? C13 C12 C11 120.1(2) . . ? O5 C11 C12 123.2(2) . . ? O5 C11 C10 116.9(2) . . ? C12 C11 C10 119.9(2) . . ? C9 C10 C11 119.9(2) . . ? C10 C9 C8 121.1(2) . . ? C7 N1 N2 113.3(2) . . ? C1 N2 N1 119.3(2) . . ? O2 N3 O1 122.2(2) . . ? O2 N3 C2 119.1(2) . . ? O1 N3 C2 118.7(2) . . ? O4 N4 O3 123.8(3) . . ? O4 N4 C4 119.4(3) . . ? O3 N4 C4 116.8(3) . . ? 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 N2 C1 C2 C3 177.7(2) . . . . ? C6 C1 C2 C3 -2.2(4) . . . . ? N2 C1 C2 N3 -0.4(4) . . . . ? C6 C1 C2 N3 179.7(2) . . . . ? C1 C2 C3 C4 1.1(4) . . . . ? N3 C2 C3 C4 179.3(2) . . . . ? C2 C3 C4 C5 0.0(4) . . . . ? C2 C3 C4 N4 -176.2(2) . . . . ? C3 C4 C5 C6 0.2(4) . . . . ? N4 C4 C5 C6 176.4(3) . . . . ? C4 C5 C6 C1 -1.4(4) . . . . ? N2 C1 C6 C5 -177.6(3) . . . . ? C2 C1 C6 C5 2.3(4) . . . . ? N1 C7 C8 C9 -0.7(4) . . . . ? N1 C7 C8 C13 -179.9(2) . . . . ? C9 C8 C13 C12 -0.7(4) . . . . ? C7 C8 C13 C12 178.5(2) . . . . ? C8 C13 C12 C11 -0.7(4) . . . . ? C13 C12 C11 O5 -179.2(2) . . . . ? C13 C12 C11 C10 1.6(4) . . . . ? O5 C11 C10 C9 179.5(2) . . . . ? C12 C11 C10 C9 -1.2(4) . . . . ? C11 C10 C9 C8 -0.1(4) . . . . ? C13 C8 C9 C10 1.1(4) . . . . ? C7 C8 C9 C10 -178.1(2) . . . . ? C8 C7 N1 N2 -179.9(2) . . . . ? C6 C1 N2 N1 1.9(4) . . . . ? C2 C1 N2 N1 -178.0(2) . . . . ? C7 N1 N2 C1 178.9(2) . . . . ? C3 C2 N3 O2 3.8(3) . . . . ? C1 C2 N3 O2 -177.9(2) . . . . ? C3 C2 N3 O1 -177.1(2) . . . . ? C1 C2 N3 O1 1.2(4) . . . . ? C3 C4 N4 O4 -5.6(4) . . . . ? C5 C4 N4 O4 178.1(3) . . . . ? C3 C4 N4 O3 174.0(3) . . . . ? C5 C4 N4 O3 -2.3(4) . . . . ? 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 N2 H2 O1 1.0089(10) 1.90(2) 2.615(3) 125(2) . N2 H2 O1 1.0089(10) 2.484(13) 3.425(3) 155(2) 3_665 O5 H5A O3 0.9829(11) 1.825(5) 2.806(3) 175(4) 4_585 C7 H7 O1 0.99(3) 2.57(3) 3.492(3) 156(2) 3_665 C7 H7 O2 0.99(3) 2.66(3) 3.558(3) 152(2) 3_665 C13 H13 O2 0.93 2.64 3.506(3) 155.7 3_665 _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 73.95 _diffrn_measured_fraction_theta_full 0.907 _refine_diff_density_max 0.227 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.059 #===END data_compound_4 _database_code_CSD 177495 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-[(2,4-Dinitro-phenyl)-hydrazonomethyl]-phenol * 0.5 MeCN ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11.50 N4.50 O5' _chemical_formula_weight 322.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.002(2) _cell_length_b 9.175(2) _cell_length_c 27.266(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.15(3) _cell_angle_gamma 90.00 _cell_volume 2935.2(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15 _cell_measurement_theta_min 10.97 _cell_measurement_theta_max 42.36 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.972 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Mach3 _diffrn_measurement_method omega\2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 3000 _diffrn_standards_decay_% 1 _diffrn_reflns_number 1434 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 72.54 _reflns_number_total 1434 _reflns_number_gt 1416 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Express, Nonius BV' _computing_cell_refinement 'Express, Nonius BV' _computing_data_reduction 'OpenMolen 2.2' _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 w=1/[\s^2^(Fo^2^)+(0.0573P)^2^+1.4569P] 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 SHELXL _refine_ls_extinction_coef 0.0048(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1434 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1119 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _refine_ls_shift/su_max 0.455 _refine_ls_shift/su_mean 0.017 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4420(3) 0.0374(3) 0.58153(11) 0.0462(8) Uani 1 d . . . C2 C 0.4324(3) 0.1633(3) 0.61095(11) 0.0463(8) Uani 1 d . . . C3 C 0.5003(3) 0.1814(4) 0.65834(11) 0.0502(8) Uani 1 d . . . H3 H 0.4921 0.2636 0.6773 0.060 Uiso 1 calc R . . C4 C 0.5790(3) 0.0778(3) 0.67699(11) 0.0484(8) Uani 1 d . . . C5 C 0.5926(3) -0.0459(4) 0.64954(13) 0.0559(9) Uani 1 d . . . H5 H 0.6473 -0.1152 0.6627 0.067 Uiso 1 calc R . . C6 C 0.5252(3) -0.0651(3) 0.60318(12) 0.0540(9) Uani 1 d . . . H6 H 0.5345 -0.1488 0.5852 0.065 Uiso 1 calc R . . C7 C 0.3212(3) -0.1241(4) 0.46749(12) 0.0521(8) Uani 1 d . . . H7 H 0.258(3) -0.049(4) 0.4556(12) 0.065(10) Uiso 1 d . . . C8 C 0.3232(3) -0.2515(3) 0.43602(11) 0.0487(8) Uani 1 d . . . C9 C 0.3995(3) -0.3668(4) 0.45016(12) 0.0596(9) Uani 1 d . . . H9 H 0.4508 -0.3636 0.4809 0.072 Uiso 1 calc R . . C10 C 0.3994(3) -0.4847(4) 0.41918(12) 0.0655(10) Uani 1 d . . . H10 H 0.4509 -0.5604 0.4288 0.079 Uiso 1 calc R . . C11 C 0.3226(3) -0.4910(4) 0.37349(12) 0.0565(9) Uani 1 d . . . C12 C 0.2474(3) -0.3783(4) 0.35862(12) 0.0549(9) Uani 1 d . . . H12 H 0.1966 -0.3818 0.3277 0.066 Uiso 1 calc R . . C13 C 0.2479(3) -0.2600(4) 0.38998(11) 0.0528(8) Uani 1 d . . . H13 H 0.1966 -0.1843 0.3800 0.063 Uiso 1 calc R . . N1 N 0.3901(2) -0.1110(3) 0.50987(9) 0.0524(7) Uani 1 d . . . N2 N 0.3769(3) 0.0154(3) 0.53546(10) 0.0537(7) Uani 1 d . . . H2 H 0.327(3) 0.081(4) 0.5222(12) 0.056(11) Uiso 1 d . . . N3 N 0.3541(3) 0.2797(3) 0.59327(10) 0.0576(7) Uani 1 d . . . N4 N 0.6512(3) 0.0995(4) 0.72626(11) 0.0645(8) Uani 1 d . . . O1 O 0.2916(2) 0.2702(3) 0.55119(9) 0.0858(9) Uani 1 d . . . O2 O 0.3509(2) 0.3861(3) 0.61976(9) 0.0783(8) Uani 1 d . . . O3 O 0.6350(2) 0.2041(4) 0.75151(9) 0.0921(10) Uani 1 d . . . O4 O 0.7275(2) 0.0103(4) 0.74086(10) 0.0910(9) Uani 1 d . . . O5 O 0.3264(3) -0.6120(3) 0.34475(9) 0.0839(9) Uani 1 d . . . H5A H 0.2739 -0.6042 0.3160 0.101 Uiso 1 calc R . . C1' C 0.0000 0.1962(8) 0.7500 0.0805(17) Uani 1 d S . . C2' C 0.0000 0.0403(8) 0.7500 0.150(4) Uani 1 d S . . H2'1 H -0.0752 0.0040 0.7552 0.180 Uiso 0.50 calc PR . . H2'2 H 0.0621 0.0040 0.7777 0.180 Uiso 0.50 calc PR . . H2'3 H 0.0130 0.0040 0.7171 0.180 Uiso 0.50 calc PR . . N1' N 0.0000 0.3170(7) 0.7500 0.110(2) Uani 1 d S . . 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 0.0523(19) 0.0385(17) 0.0488(18) 0.0013(14) 0.0124(15) -0.0003(15) C2 0.053(2) 0.0372(17) 0.0489(18) 0.0027(14) 0.0112(15) 0.0056(15) C3 0.057(2) 0.0453(19) 0.0498(18) -0.0030(15) 0.0143(15) 0.0000(16) C4 0.051(2) 0.0520(19) 0.0428(17) 0.0045(15) 0.0105(14) 0.0017(17) C5 0.058(2) 0.048(2) 0.061(2) 0.0095(17) 0.0121(17) 0.0087(17) C6 0.066(2) 0.0398(17) 0.059(2) -0.0004(16) 0.0200(18) 0.0079(17) C7 0.063(2) 0.0457(19) 0.0480(19) -0.0012(16) 0.0125(17) 0.0021(17) C8 0.059(2) 0.0419(17) 0.0457(17) -0.0009(14) 0.0110(15) -0.0026(16) C9 0.078(3) 0.050(2) 0.0466(18) 0.0003(16) 0.0039(16) 0.0069(19) C10 0.086(3) 0.049(2) 0.055(2) 0.0017(17) -0.0012(19) 0.015(2) C11 0.079(2) 0.0423(18) 0.0478(18) -0.0050(15) 0.0118(17) 0.0036(18) C12 0.068(2) 0.0494(19) 0.0452(18) 0.0002(16) 0.0064(16) 0.0018(18) C13 0.059(2) 0.0468(18) 0.0526(19) 0.0039(16) 0.0120(16) 0.0061(17) N1 0.068(2) 0.0412(15) 0.0508(16) -0.0066(13) 0.0183(14) 0.0026(14) N2 0.068(2) 0.0422(16) 0.0497(16) -0.0048(13) 0.0092(14) 0.0078(15) N3 0.0671(19) 0.0489(17) 0.0533(16) -0.0077(14) 0.0046(14) 0.0132(15) N4 0.056(2) 0.083(2) 0.0538(17) 0.0082(17) 0.0090(15) -0.0029(19) O1 0.110(2) 0.0668(18) 0.0639(16) -0.0110(13) -0.0190(15) 0.0373(16) O2 0.097(2) 0.0562(15) 0.0753(17) -0.0192(14) 0.0038(14) 0.0292(15) O3 0.094(2) 0.113(2) 0.0621(17) -0.0287(17) -0.0012(14) 0.0061(19) O4 0.0741(19) 0.110(2) 0.0783(19) 0.0170(17) -0.0068(15) 0.020(2) O5 0.124(2) 0.0556(15) 0.0594(15) -0.0181(13) -0.0086(14) 0.0251(16) C1' 0.072(4) 0.075(4) 0.097(5) 0.000 0.024(3) 0.000 C2' 0.096(6) 0.075(5) 0.289(12) 0.000 0.061(7) 0.000 N1' 0.149(6) 0.077(4) 0.107(4) 0.000 0.036(4) 0.000 _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 N2 1.348(4) . ? C1 C6 1.409(4) . ? C1 C2 1.425(4) . ? C2 C3 1.385(4) . ? C2 N3 1.437(4) . ? C3 C4 1.362(4) . ? C4 C5 1.388(4) . ? C4 N4 1.451(4) . ? C5 C6 1.361(5) . ? C7 N1 1.277(4) . ? C7 C8 1.453(4) . ? C8 C13 1.386(4) . ? C8 C9 1.399(4) . ? C9 C10 1.372(5) . ? C10 C11 1.386(5) . ? C11 O5 1.365(4) . ? C11 C12 1.376(4) . ? C12 C13 1.381(4) . ? N1 N2 1.379(3) . ? N3 O2 1.220(3) . ? N3 O1 1.235(3) . ? N4 O3 1.220(4) . ? N4 O4 1.230(4) . ? C1' N1' 1.109(7) . ? C1' C2' 1.430(9) . ? 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 N2 C1 C6 120.7(3) . . ? N2 C1 C2 123.2(3) . . ? C6 C1 C2 116.1(3) . . ? C3 C2 C1 121.4(3) . . ? C3 C2 N3 116.0(3) . . ? C1 C2 N3 122.6(3) . . ? C4 C3 C2 119.4(3) . . ? C3 C4 C5 121.4(3) . . ? C3 C4 N4 118.8(3) . . ? C5 C4 N4 119.8(3) . . ? C6 C5 C4 119.5(3) . . ? C5 C6 C1 122.2(3) . . ? N1 C7 C8 121.5(3) . . ? C13 C8 C9 118.1(3) . . ? C13 C8 C7 119.4(3) . . ? C9 C8 C7 122.5(3) . . ? C10 C9 C8 120.7(3) . . ? C9 C10 C11 120.0(3) . . ? O5 C11 C12 122.8(3) . . ? O5 C11 C10 117.0(3) . . ? C12 C11 C10 120.3(3) . . ? C11 C12 C13 119.4(3) . . ? C12 C13 C8 121.5(3) . . ? C7 N1 N2 114.6(3) . . ? C1 N2 N1 119.5(3) . . ? O2 N3 O1 121.2(3) . . ? O2 N3 C2 119.7(3) . . ? O1 N3 C2 119.1(3) . . ? O3 N4 O4 122.5(3) . . ? O3 N4 C4 119.7(3) . . ? O4 N4 C4 117.8(3) . . ? N1' C1' C2' 180.000(7) . . ? 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 N2 C1 C2 C3 179.5(3) . . . . ? C6 C1 C2 C3 -1.0(5) . . . . ? N2 C1 C2 N3 -1.7(5) . . . . ? C6 C1 C2 N3 177.9(3) . . . . ? C1 C2 C3 C4 1.0(5) . . . . ? N3 C2 C3 C4 -178.0(3) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C2 C3 C4 N4 178.7(3) . . . . ? C3 C4 C5 C6 -0.6(5) . . . . ? N4 C4 C5 C6 -179.5(3) . . . . ? C4 C5 C6 C1 0.6(5) . . . . ? N2 C1 C6 C5 179.7(3) . . . . ? C2 C1 C6 C5 0.2(5) . . . . ? N1 C7 C8 C13 -179.1(3) . . . . ? N1 C7 C8 C9 0.3(5) . . . . ? C13 C8 C9 C10 0.1(5) . . . . ? C7 C8 C9 C10 -179.4(3) . . . . ? C8 C9 C10 C11 -0.6(6) . . . . ? C9 C10 C11 O5 -179.4(3) . . . . ? C9 C10 C11 C12 1.1(6) . . . . ? O5 C11 C12 C13 179.4(3) . . . . ? C10 C11 C12 C13 -1.0(5) . . . . ? C11 C12 C13 C8 0.5(5) . . . . ? C9 C8 C13 C12 0.0(5) . . . . ? C7 C8 C13 C12 179.4(3) . . . . ? C8 C7 N1 N2 -179.5(3) . . . . ? C6 C1 N2 N1 1.8(4) . . . . ? C2 C1 N2 N1 -178.7(3) . . . . ? C7 N1 N2 C1 177.2(3) . . . . ? C3 C2 N3 O2 0.1(5) . . . . ? C1 C2 N3 O2 -178.8(3) . . . . ? C3 C2 N3 O1 179.8(3) . . . . ? C1 C2 N3 O1 0.8(5) . . . . ? C3 C4 N4 O3 5.2(5) . . . . ? C5 C4 N4 O3 -176.0(3) . . . . ? C3 C4 N4 O4 -174.6(3) . . . . ? C5 C4 N4 O4 4.3(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 N2 H2 O1 0.87(3) 1.99(3) 2.624(4) 129(3) . C2' H2'1 O4 1.00 2.32 3.239(3) 152.4 1_455 C5 H5 O5 0.93 2.54 3.279(4) 137.1 5_646 C7 H7 O1 1.03(3) 2.62(3) 3.513(4) 145(2) 7_556 N2 H2 O1 0.87(3) 2.59(3) 3.395(4) 155(3) 7_556 C7 H7 O2 1.03(3) 2.65(3) 3.553(5) 146(2) 7_556 C13 H13 O2 0.93 2.79 3.621(4) 148.5 7_556 C3 H3 O3 0.93 2.77 3.225(4) 111.6 2_656 C2' H2'2 O4 1.00 2.68 3.239(3) 115.6 2_656 O5 H5A N4 0.90 2.58 3.466(4) 169.9 8_445 O5 H5A O3 0.90 2.34 3.162(4) 151.8 8_445 C12 H12 O4 0.93 2.74 3.393(4) 128.0 8_445 O5 H5A O4 0.90 2.18 2.982(4) 147.4 8_445 _diffrn_measured_fraction_theta_max 0.231 _diffrn_reflns_theta_full 72.54 _diffrn_measured_fraction_theta_full 0.231 _refine_diff_density_max 0.174 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.056 #===END