# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Srinivas Basavoju' _publ_contact_author_email basavoju_s@yahoo.com loop_ _publ_author_name A.Alhalaweh S.George S.Basavoju S.Childs S.A.A.Rizvi S.Velaga data_'Nitrofurantoin:citricacid' _database_code_depnum_ccdc_archive 'CCDC 835423' #TrackingRef '- NTF_CitricAcidF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic 'Nitrofurantoin:citric acid cocrystal' _chemical_name_common 'Nitrofurantoin:citric acid cocrystal' _chemical_melting_point ? _chemical_formula_moiety 'C8 H6 N4 O5, C6 H8 O7 ' _chemical_formula_sum 'C14 H14 N4 O12 ' _chemical_formula_weight 430.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M '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 13.444(1) _cell_length_b 11.480(1) _cell_length_c 12.434(1) _cell_angle_alpha 90.000 _cell_angle_beta 113.736(1) _cell_angle_gamma 90.000 _cell_volume 1756.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3065 _cell_measurement_theta_min 3.313 _cell_measurement_theta_max 27.878 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'kappa CCD' _diffrn_measurement_method psi-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5741 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3643 _reflns_number_gt 2214 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor,1997)' _computing_data_reduction "HKL Denzo and Scalepack'(Otwinowski & Minor,1997)" _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 2001)' _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^)+(0.0574P)^2^+0.1352P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3643 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0936 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1268 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 0.8269(2) 0.1503(2) 0.9213(2) 0.0375(6) Uani 1 1 d . . . H1A H 0.903(2) 0.139(2) 0.978(2) 0.046(7) Uiso 1 1 d . . . H1B H 0.779(2) 0.169(2) 0.965(2) 0.056(8) Uiso 1 1 d . . . C2 C 0.7856(2) 0.0474(2) 0.8400(2) 0.0356(6) Uani 1 1 d . . . C3 C 0.77862(19) 0.2060(2) 0.72612(19) 0.0323(5) Uani 1 1 d . . . C4 C 0.86453(19) 0.3935(2) 0.9677(2) 0.0322(5) Uani 1 1 d . . . H4 H 0.8818(19) 0.3390(19) 1.034(2) 0.042(7) Uiso 1 1 d . . . C5 C 0.87593(18) 0.51645(19) 0.99431(19) 0.0299(5) Uani 1 1 d . . . C6 C 0.8584(2) 0.6169(2) 0.9311(2) 0.0374(6) Uani 1 1 d . . . H6 H 0.8343(19) 0.6225(19) 0.851(2) 0.039(7) Uiso 1 1 d . . . C7 C 0.8858(2) 0.7098(2) 1.0115(2) 0.0375(6) Uani 1 1 d . . . H7 H 0.8853(18) 0.795(2) 0.9948(19) 0.039(6) Uiso 1 1 d . . . C8 C 0.91747(19) 0.65950(19) 1.1173(2) 0.0332(5) Uani 1 1 d . . . C9 C 0.48428(19) 0.8461(2) 0.67587(19) 0.0323(5) Uani 1 1 d . . . C10 C 0.5076(2) 0.7430(2) 0.6161(2) 0.0357(6) Uani 1 1 d . . . H10A H 0.515(2) 0.678(2) 0.663(2) 0.050(8) Uiso 1 1 d . . . H10B H 0.447(2) 0.729(2) 0.543(2) 0.044(7) Uiso 1 1 d . . . C11 C 0.61006(18) 0.75688(19) 0.59134(19) 0.0303(5) Uani 1 1 d . . . C12 C 0.6295(2) 0.64974(19) 0.5286(2) 0.0324(5) Uani 1 1 d . . . H12A H 0.6861(19) 0.6644(18) 0.5044(19) 0.032(6) Uiso 1 1 d . . . H12B H 0.5643(19) 0.6311(18) 0.463(2) 0.031(6) Uiso 1 1 d . . . C13 C 0.6621(2) 0.54434(19) 0.6064(2) 0.0346(6) Uani 1 1 d . . . C14 C 0.59777(19) 0.86226(19) 0.5117(2) 0.0332(5) Uani 1 1 d . . . N1 N 0.82324(15) 0.24313(15) 0.83961(15) 0.0314(4) Uani 1 1 d . . . N2 N 0.75982(17) 0.08844(17) 0.72865(18) 0.0366(5) Uani 1 1 d . . . H2 H 0.735(2) 0.044(2) 0.668(3) 0.062(9) Uiso 1 1 d . . . N3 N 0.83469(15) 0.36099(15) 0.86136(16) 0.0315(5) Uani 1 1 d . . . N4 N 0.95705(17) 0.7081(2) 1.23139(19) 0.0465(6) Uani 1 1 d . . . O1 O 0.77564(15) -0.05243(14) 0.86592(15) 0.0476(5) Uani 1 1 d . . . O2 O 0.75946(15) 0.26521(14) 0.63902(14) 0.0448(5) Uani 1 1 d . . . O3 O 0.91239(13) 0.54184(12) 1.11143(12) 0.0336(4) Uani 1 1 d . . . O4 O 0.97267(17) 0.81393(18) 1.23924(18) 0.0654(6) Uani 1 1 d . . . O5 O 0.97407(19) 0.64259(19) 1.31477(17) 0.0694(6) Uani 1 1 d . . . O6 O 0.53498(14) 0.93699(13) 0.69486(15) 0.0402(4) Uani 1 1 d . . . O7 O 0.40186(14) 0.82804(16) 0.70602(17) 0.0472(5) Uani 1 1 d . . . H7A H 0.393(3) 0.893(3) 0.747(3) 0.088(11) Uiso 1 1 d . . . O8 O 0.66030(14) 0.94307(14) 0.53247(14) 0.0413(4) Uani 1 1 d . . . O9 O 0.50901(15) 0.85451(14) 0.41359(16) 0.0520(5) Uani 1 1 d . . . H9 H 0.5015 0.9216 0.3645 0.078 Uiso 1 1 d R . . O10 O 0.60650(15) 0.50041(15) 0.65114(17) 0.0515(5) Uani 1 1 d . . . O11 O 0.75685(17) 0.50387(17) 0.6196(2) 0.0705(7) Uani 1 1 d . . . H11 H 0.7621 0.4430 0.6566 0.106 Uiso 1 1 d R . . O12 O 0.70480(13) 0.76705(15) 0.69491(14) 0.0384(4) Uani 1 1 d . . . H12 H 0.707(2) 0.827(2) 0.732(2) 0.053(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0475(17) 0.0315(13) 0.0300(13) -0.0014(10) 0.0118(13) -0.0010(12) C2 0.0404(15) 0.0300(13) 0.0347(13) 0.0000(10) 0.0135(12) 0.0020(11) C3 0.0367(14) 0.0301(12) 0.0318(13) -0.0022(10) 0.0156(11) -0.0019(10) C4 0.0339(13) 0.0318(13) 0.0314(13) -0.0006(10) 0.0137(11) -0.0016(10) C5 0.0284(12) 0.0337(12) 0.0265(12) -0.0014(10) 0.0099(10) -0.0004(10) C6 0.0412(15) 0.0364(14) 0.0324(14) 0.0022(11) 0.0127(12) 0.0003(11) C7 0.0396(15) 0.0272(13) 0.0460(15) 0.0011(11) 0.0175(13) -0.0010(10) C8 0.0310(13) 0.0301(12) 0.0373(13) -0.0085(10) 0.0125(11) -0.0006(10) C9 0.0331(13) 0.0350(13) 0.0302(12) 0.0032(10) 0.0141(11) 0.0034(11) C10 0.0381(15) 0.0319(13) 0.0392(14) -0.0019(11) 0.0178(13) -0.0006(11) C11 0.0281(12) 0.0312(12) 0.0288(12) -0.0021(9) 0.0086(10) -0.0001(10) C12 0.0376(15) 0.0286(12) 0.0340(13) -0.0033(10) 0.0177(13) -0.0013(11) C13 0.0394(15) 0.0282(12) 0.0399(14) -0.0036(10) 0.0199(12) -0.0006(11) C14 0.0340(14) 0.0323(13) 0.0344(13) -0.0030(10) 0.0151(12) 0.0005(11) N1 0.0381(11) 0.0268(10) 0.0285(10) -0.0019(8) 0.0125(9) -0.0025(8) N2 0.0500(14) 0.0292(11) 0.0305(11) -0.0048(9) 0.0159(10) -0.0049(9) N3 0.0327(11) 0.0260(10) 0.0365(11) -0.0039(8) 0.0149(9) -0.0024(8) N4 0.0412(14) 0.0512(14) 0.0451(13) -0.0174(12) 0.0153(12) -0.0037(11) O1 0.0674(13) 0.0284(9) 0.0422(10) 0.0005(7) 0.0170(10) -0.0016(8) O2 0.0658(13) 0.0384(10) 0.0328(9) 0.0015(8) 0.0224(9) -0.0020(8) O3 0.0375(9) 0.0333(9) 0.0277(8) -0.0027(6) 0.0106(7) -0.0008(7) O4 0.0688(14) 0.0534(12) 0.0749(14) -0.0321(11) 0.0297(12) -0.0126(11) O5 0.0831(17) 0.0808(15) 0.0339(11) -0.0088(11) 0.0126(11) -0.0020(12) O6 0.0449(10) 0.0319(9) 0.0484(10) 0.0002(7) 0.0236(9) 0.0002(8) O7 0.0448(11) 0.0464(11) 0.0618(12) -0.0108(9) 0.0334(10) -0.0018(8) O8 0.0467(11) 0.0412(10) 0.0379(10) -0.0044(7) 0.0189(9) -0.0143(8) O9 0.0513(12) 0.0375(10) 0.0467(11) 0.0096(8) -0.0016(9) -0.0060(8) O10 0.0545(12) 0.0449(11) 0.0696(13) 0.0168(9) 0.0402(11) 0.0042(9) O11 0.0688(15) 0.0578(13) 0.1089(18) 0.0427(12) 0.0610(14) 0.0274(11) O12 0.0371(10) 0.0380(10) 0.0342(9) -0.0066(8) 0.0081(8) 0.0029(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.459(3) . ? C1 C2 1.508(3) . ? C1 H1A 0.99(3) . ? C1 H1B 1.02(3) . ? C2 O1 1.212(3) . ? C2 N2 1.368(3) . ? C3 O2 1.215(3) . ? C3 N1 1.361(3) . ? C3 N2 1.376(3) . ? C4 N3 1.274(3) . ? C4 C5 1.443(3) . ? C4 H4 0.98(2) . ? C5 C6 1.361(3) . ? C5 O3 1.368(2) . ? C6 C7 1.406(3) . ? C6 H6 0.92(2) . ? C7 C8 1.339(3) . ? C7 H7 1.00(2) . ? C8 O3 1.353(2) . ? C8 N4 1.414(3) . ? C9 O6 1.216(3) . ? C9 O7 1.321(3) . ? C9 C10 1.496(3) . ? C10 C11 1.536(3) . ? C10 H10A 0.93(3) . ? C10 H10B 0.96(3) . ? C11 O12 1.405(3) . ? C11 C14 1.529(3) . ? C11 C12 1.534(3) . ? C12 C13 1.500(3) . ? C12 H12A 0.94(2) . ? C12 H12B 0.95(2) . ? C13 O10 1.208(3) . ? C13 O11 1.302(3) . ? C14 O8 1.208(3) . ? C14 O9 1.322(3) . ? N1 N3 1.376(2) . ? N2 H2 0.86(3) . ? N4 O5 1.225(3) . ? N4 O4 1.230(3) . ? O7 H7A 0.93(3) . ? O9 H9 0.9626 . ? O11 H11 0.8235 . ? O12 H12 0.82(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 N1 C1 C2 101.86(18) . . ? N1 C1 H1A 109.1(14) . . ? C2 C1 H1A 111.7(14) . . ? N1 C1 H1B 111.2(15) . . ? C2 C1 H1B 112.6(15) . . ? H1A C1 H1B 110(2) . . ? O1 C2 N2 125.8(2) . . ? O1 C2 C1 127.8(2) . . ? N2 C2 C1 106.5(2) . . ? O2 C3 N1 126.6(2) . . ? O2 C3 N2 126.5(2) . . ? N1 C3 N2 106.98(19) . . ? N3 C4 C5 119.0(2) . . ? N3 C4 H4 123.4(13) . . ? C5 C4 H4 117.6(13) . . ? C6 C5 O3 109.80(19) . . ? C6 C5 C4 135.9(2) . . ? O3 C5 C4 114.31(19) . . ? C5 C6 C7 107.3(2) . . ? C5 C6 H6 126.2(14) . . ? C7 C6 H6 126.6(14) . . ? C8 C7 C6 105.1(2) . . ? C8 C7 H7 126.7(13) . . ? C6 C7 H7 128.1(13) . . ? C7 C8 O3 112.8(2) . . ? C7 C8 N4 131.1(2) . . ? O3 C8 N4 116.0(2) . . ? O6 C9 O7 123.2(2) . . ? O6 C9 C10 124.2(2) . . ? O7 C9 C10 112.6(2) . . ? C9 C10 C11 113.7(2) . . ? C9 C10 H10A 108.6(16) . . ? C11 C10 H10A 109.3(16) . . ? C9 C10 H10B 109.4(14) . . ? C11 C10 H10B 108.4(15) . . ? H10A C10 H10B 107(2) . . ? O12 C11 C14 110.45(18) . . ? O12 C11 C12 104.82(18) . . ? C14 C11 C12 107.52(17) . . ? O12 C11 C10 112.34(19) . . ? C14 C11 C10 109.87(19) . . ? C12 C11 C10 111.65(19) . . ? C13 C12 C11 112.57(19) . . ? C13 C12 H12A 106.7(14) . . ? C11 C12 H12A 110.2(13) . . ? C13 C12 H12B 107.4(13) . . ? C11 C12 H12B 109.1(13) . . ? H12A C12 H12B 110.9(19) . . ? O10 C13 O11 123.2(2) . . ? O10 C13 C12 124.0(2) . . ? O11 C13 C12 112.7(2) . . ? O8 C14 O9 122.7(2) . . ? O8 C14 C11 125.8(2) . . ? O9 C14 C11 111.49(19) . . ? C3 N1 N3 118.67(18) . . ? C3 N1 C1 111.72(18) . . ? N3 N1 C1 127.70(18) . . ? C2 N2 C3 112.8(2) . . ? C2 N2 H2 122.4(19) . . ? C3 N2 H2 124.8(19) . . ? C4 N3 N1 117.14(19) . . ? O5 N4 O4 124.8(2) . . ? O5 N4 C8 118.2(2) . . ? O4 N4 C8 116.9(2) . . ? C8 O3 C5 105.01(17) . . ? C9 O7 H7A 110(2) . . ? C14 O9 H9 110.9 . . ? C13 O11 H11 103.4 . . ? C11 O12 H12 114(2) . . ? 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 N1 C1 C2 O1 178.1(2) . . . . ? N1 C1 C2 N2 -2.5(3) . . . . ? N3 C4 C5 C6 3.1(4) . . . . ? N3 C4 C5 O3 -177.6(2) . . . . ? O3 C5 C6 C7 0.5(3) . . . . ? C4 C5 C6 C7 179.8(3) . . . . ? C5 C6 C7 C8 -0.2(3) . . . . ? C6 C7 C8 O3 -0.2(3) . . . . ? C6 C7 C8 N4 177.9(2) . . . . ? O6 C9 C10 C11 6.0(4) . . . . ? O7 C9 C10 C11 -174.1(2) . . . . ? C9 C10 C11 O12 63.4(3) . . . . ? C9 C10 C11 C14 -60.0(3) . . . . ? C9 C10 C11 C12 -179.2(2) . . . . ? O12 C11 C12 C13 52.4(3) . . . . ? C14 C11 C12 C13 170.0(2) . . . . ? C10 C11 C12 C13 -69.4(3) . . . . ? C11 C12 C13 O10 60.4(3) . . . . ? C11 C12 C13 O11 -120.4(2) . . . . ? O12 C11 C14 O8 0.9(3) . . . . ? C12 C11 C14 O8 -113.0(3) . . . . ? C10 C11 C14 O8 125.3(2) . . . . ? O12 C11 C14 O9 180.00(19) . . . . ? C12 C11 C14 O9 66.2(2) . . . . ? C10 C11 C14 O9 -55.5(2) . . . . ? O2 C3 N1 N3 10.1(4) . . . . ? N2 C3 N1 N3 -170.18(18) . . . . ? O2 C3 N1 C1 175.6(2) . . . . ? N2 C3 N1 C1 -4.7(3) . . . . ? C2 C1 N1 C3 4.5(3) . . . . ? C2 C1 N1 N3 168.3(2) . . . . ? O1 C2 N2 C3 179.2(2) . . . . ? C1 C2 N2 C3 -0.2(3) . . . . ? O2 C3 N2 C2 -177.3(2) . . . . ? N1 C3 N2 C2 3.0(3) . . . . ? C5 C4 N3 N1 -179.05(19) . . . . ? C3 N1 N3 C4 171.9(2) . . . . ? C1 N1 N3 C4 9.0(3) . . . . ? C7 C8 N4 O5 175.3(3) . . . . ? O3 C8 N4 O5 -6.6(3) . . . . ? C7 C8 N4 O4 -5.3(4) . . . . ? O3 C8 N4 O4 172.8(2) . . . . ? C7 C8 O3 C5 0.5(3) . . . . ? N4 C8 O3 C5 -177.95(19) . . . . ? C6 C5 O3 C8 -0.6(2) . . . . ? C4 C5 O3 C8 179.91(19) . . . . ? 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 O8 0.86(3) 1.95(3) 2.810(3) 172(3) 1_545 O7 H7A O10 0.93(3) 1.77(3) 2.691(2) 169(3) 2_656 O9 H9 O6 0.96 1.77 2.694(2) 160.0 3_676 O11 H11 O2 0.82 2.05 2.749(2) 142.3 . O11 H11 N3 0.82 2.51 3.207(3) 142.5 . O12 H12 O1 0.82(3) 2.07(3) 2.845(2) 156(3) 1_565 O12 H12 O6 0.82(3) 2.51(3) 3.003(2) 119(2) . _diffrn_measured_fraction_theta_max 0.901 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.901 _refine_diff_density_max 0.200 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.052 # Attachment '- NTF_vanillin.cif' data_NTF_vanillin _database_code_depnum_ccdc_archive 'CCDC 835424' #TrackingRef '- NTF_vanillin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 N4 O11' _chemical_formula_weight 542.46 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 P2(1)/c 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 7.2120(6) _cell_length_b 27.7094(17) _cell_length_c 12.0909(9) _cell_angle_alpha 90.00 _cell_angle_beta 91.789(8) _cell_angle_gamma 90.00 _cell_volume 2415.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 587 _cell_measurement_theta_min 6.03 _cell_measurement_theta_max 60.25 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 1.028 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6720 _exptl_absorpt_correction_T_max 0.9504 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8674 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 6.03 _diffrn_reflns_theta_max 65.07 _reflns_number_total 3613 _reflns_number_gt 2613 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.874 The crystal was an extremely thin needle and the intensities of the high-angle data were very weak even with long counting times so the number of data measured was low. ; _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^)+(0.1080P)^2^+5.9000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3613 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1111 _refine_ls_R_factor_gt 0.0891 _refine_ls_wR_factor_ref 0.2326 _refine_ls_wR_factor_gt 0.2177 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 0.4140(8) 0.46148(16) 0.5843(4) 0.0427(12) Uani 1 1 d . . . H1A H 0.2981 0.4783 0.5611 0.051 Uiso 1 1 calc R . . H1B H 0.4990 0.4607 0.5217 0.051 Uiso 1 1 calc R . . C2 C 0.5038(7) 0.48481(16) 0.6847(4) 0.0409(12) Uani 1 1 d . . . C3 C 0.4451(7) 0.40544(15) 0.7296(4) 0.0394(11) Uani 1 1 d . . . C4 C 0.2518(7) 0.38348(16) 0.4667(4) 0.0399(11) Uani 1 1 d . . . H4A H 0.2637 0.4148 0.4356 0.048 Uiso 1 1 calc R . . C5 C 0.1772(7) 0.34435(17) 0.4013(4) 0.0411(12) Uani 1 1 d . . . C6 C 0.1492(8) 0.29647(18) 0.4218(5) 0.0512(14) Uani 1 1 d . . . H6A H 0.1731 0.2797 0.4894 0.061 Uiso 1 1 calc R . . C7 C 0.0772(8) 0.27706(19) 0.3212(6) 0.0591(16) Uani 1 1 d . . . H7A H 0.0442 0.2444 0.3072 0.071 Uiso 1 1 calc R . . C8 C 0.0648(8) 0.31337(19) 0.2502(5) 0.0508(14) Uani 1 1 d . . . C9 C -0.0261(7) 0.47552(16) 0.6884(4) 0.0394(11) Uani 1 1 d . . . C10 C -0.0073(7) 0.43754(16) 0.7660(4) 0.0399(11) Uani 1 1 d . . . C11 C 0.0804(7) 0.44549(17) 0.8659(4) 0.0417(12) Uani 1 1 d . . . H11A H 0.0928 0.4198 0.9177 0.050 Uiso 1 1 calc R . . C12 C 0.1530(7) 0.49144(17) 0.8930(4) 0.0426(12) Uani 1 1 d . . . C13 C 0.1311(7) 0.52865(17) 0.8165(4) 0.0455(13) Uani 1 1 d . . . H13A H 0.1780 0.5599 0.8341 0.055 Uiso 1 1 calc R . . C14 C 0.0430(8) 0.52091(16) 0.7161(4) 0.0456(13) Uani 1 1 d . . . H14A H 0.0291 0.5468 0.6650 0.055 Uiso 1 1 calc R . . C15 C -0.0728(9) 0.35520(18) 0.8047(5) 0.0607(17) Uani 1 1 d . . . H15A H -0.1323 0.3269 0.7705 0.091 Uiso 1 1 calc R . . H15B H -0.1357 0.3635 0.8729 0.091 Uiso 1 1 calc R . . H15C H 0.0579 0.3480 0.8222 0.091 Uiso 1 1 calc R . . C16 C 0.2517(7) 0.49910(18) 0.9972(4) 0.0453(13) Uani 1 1 d . . . H16A H 0.2591 0.4729 1.0478 0.054 Uiso 1 1 calc R . . C17 C 0.5009(7) 0.25346(16) 0.2542(4) 0.0409(12) Uani 1 1 d . . . C18 C 0.5580(7) 0.23828(16) 0.3583(4) 0.0431(12) Uani 1 1 d . . . H18A H 0.5453 0.2053 0.3781 0.052 Uiso 1 1 calc R . . C19 C 0.6334(7) 0.27051(17) 0.4340(4) 0.0437(12) Uani 1 1 d . . . H19A H 0.6714 0.2596 0.5057 0.052 Uiso 1 1 calc R . . C20 C 0.6543(7) 0.31867(17) 0.4062(4) 0.0406(11) Uani 1 1 d . . . C21 C 0.5977(7) 0.33481(16) 0.3003(4) 0.0414(12) Uani 1 1 d . . . H21A H 0.6129 0.3678 0.2810 0.050 Uiso 1 1 calc R . . C22 C 0.5211(7) 0.30349(16) 0.2251(4) 0.0403(12) Uani 1 1 d . . . C23 C 0.4843(10) 0.36354(18) 0.0860(5) 0.0579(16) Uani 1 1 d . . . H23A H 0.4335 0.3677 0.0105 0.087 Uiso 1 1 calc R . . H23B H 0.6173 0.3709 0.0878 0.087 Uiso 1 1 calc R . . H23C H 0.4208 0.3854 0.1360 0.087 Uiso 1 1 calc R . . C24 C 0.7315(7) 0.35156(18) 0.4887(4) 0.0457(13) Uani 1 1 d . . . H24A H 0.7659 0.3383 0.5588 0.055 Uiso 1 1 calc R . . N1 N 0.3763(6) 0.41279(13) 0.6254(3) 0.0406(10) Uani 1 1 d . . . N2 N 0.5204(6) 0.44915(13) 0.7647(3) 0.0409(10) Uani 1 1 d . . . H2A H 0.5729 0.4537 0.8305 0.049 Uiso 1 1 calc R . . N3 N 0.3016(6) 0.37550(13) 0.5669(3) 0.0391(10) Uani 1 1 d . . . N4 N 0.0065(7) 0.3160(2) 0.1354(5) 0.0695(17) Uani 1 1 d . . . O1 O 0.5538(5) 0.52604(11) 0.6957(3) 0.0489(9) Uani 1 1 d . . . O2 O 0.4423(5) 0.36835(11) 0.7828(3) 0.0484(9) Uani 1 1 d . . . O3 O 0.1242(5) 0.35543(12) 0.2949(3) 0.0465(9) Uani 1 1 d . . . O4 O -0.0444(7) 0.2772(2) 0.0947(5) 0.0964(19) Uani 1 1 d . . . O5 O 0.0090(8) 0.3549(2) 0.0885(4) 0.0896(17) Uani 1 1 d . . . O6 O -0.1094(6) 0.46881(11) 0.5888(3) 0.0491(10) Uani 1 1 d . . . H6 H -0.1398 0.4397 0.5817 0.074 Uiso 1 1 calc R . . O7 O -0.0848(5) 0.39486(11) 0.7299(3) 0.0467(9) Uani 1 1 d . . . O8 O 0.3260(5) 0.53686(13) 1.0246(3) 0.0524(10) Uani 1 1 d . . . O9 O 0.4216(6) 0.22453(11) 0.1774(3) 0.0502(10) Uani 1 1 d . . . H9 H 0.4094 0.1967 0.2038 0.075 Uiso 1 1 calc R . . O10 O 0.4568(5) 0.31439(11) 0.1209(3) 0.0489(9) Uani 1 1 d . . . O11 O 0.7563(6) 0.39463(12) 0.4763(3) 0.0532(10) Uani 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 0.064(4) 0.031(2) 0.033(3) 0.0042(18) -0.004(2) -0.002(2) C2 0.050(3) 0.035(3) 0.038(3) -0.0023(19) 0.003(2) 0.002(2) C3 0.055(3) 0.029(2) 0.034(3) -0.0030(18) 0.000(2) 0.0045(19) C4 0.055(3) 0.030(2) 0.034(3) 0.0015(18) -0.003(2) 0.0000(19) C5 0.046(3) 0.039(2) 0.038(3) -0.0017(19) -0.001(2) 0.003(2) C6 0.056(4) 0.037(3) 0.061(4) -0.003(2) 0.006(3) -0.003(2) C7 0.056(4) 0.035(3) 0.087(5) -0.020(3) 0.004(3) -0.006(2) C8 0.051(4) 0.049(3) 0.051(3) -0.020(2) -0.002(3) 0.005(2) C9 0.051(3) 0.032(2) 0.035(3) -0.0048(18) 0.000(2) 0.0015(19) C10 0.047(3) 0.031(2) 0.042(3) -0.0010(18) 0.000(2) 0.0009(19) C11 0.052(3) 0.037(2) 0.036(3) 0.0023(19) -0.001(2) 0.004(2) C12 0.045(3) 0.040(2) 0.043(3) -0.006(2) 0.001(2) 0.005(2) C13 0.054(3) 0.032(2) 0.050(3) -0.008(2) -0.006(3) 0.002(2) C14 0.064(4) 0.031(2) 0.042(3) -0.0003(19) -0.004(3) 0.001(2) C15 0.082(4) 0.031(3) 0.068(4) 0.008(2) -0.019(3) -0.006(2) C16 0.057(4) 0.039(3) 0.040(3) -0.004(2) 0.000(3) 0.004(2) C17 0.052(3) 0.033(2) 0.038(3) -0.0046(19) 0.003(2) 0.001(2) C18 0.056(3) 0.031(2) 0.041(3) -0.0005(19) 0.002(2) 0.003(2) C19 0.051(3) 0.041(3) 0.039(3) 0.003(2) 0.000(2) 0.008(2) C20 0.042(3) 0.044(3) 0.035(3) -0.0047(19) 0.001(2) 0.002(2) C21 0.055(3) 0.030(2) 0.039(3) -0.0020(18) 0.003(2) 0.000(2) C22 0.050(3) 0.034(2) 0.038(3) 0.0025(19) -0.001(2) 0.0012(19) C23 0.098(5) 0.039(3) 0.036(3) 0.005(2) -0.010(3) -0.002(3) C24 0.053(3) 0.045(3) 0.039(3) -0.002(2) -0.005(2) 0.002(2) N1 0.061(3) 0.0263(18) 0.034(2) 0.0007(15) -0.004(2) -0.0018(16) N2 0.059(3) 0.0307(19) 0.033(2) -0.0045(15) -0.0060(19) -0.0014(17) N3 0.052(3) 0.0289(18) 0.036(2) -0.0040(15) -0.0026(19) -0.0001(16) N4 0.057(3) 0.088(4) 0.063(4) -0.043(3) -0.015(3) 0.011(3) O1 0.070(3) 0.0273(17) 0.049(2) -0.0030(14) -0.0021(18) -0.0056(15) O2 0.076(3) 0.0308(17) 0.0379(19) 0.0029(14) -0.0056(17) 0.0005(15) O3 0.059(2) 0.0390(18) 0.041(2) -0.0085(14) -0.0090(17) 0.0023(15) O4 0.074(3) 0.112(4) 0.101(4) -0.071(3) -0.022(3) 0.007(3) O5 0.120(5) 0.090(4) 0.057(3) -0.016(3) -0.027(3) 0.030(3) O6 0.078(3) 0.0327(17) 0.036(2) 0.0004(13) -0.0100(18) -0.0052(16) O7 0.068(3) 0.0271(16) 0.044(2) -0.0006(13) -0.0044(18) -0.0056(14) O8 0.062(3) 0.049(2) 0.045(2) -0.0085(16) -0.0070(19) -0.0010(17) O9 0.079(3) 0.0306(16) 0.041(2) -0.0015(14) -0.0034(18) -0.0064(16) O10 0.078(3) 0.0324(17) 0.0357(19) 0.0012(13) -0.0060(18) -0.0028(15) O11 0.077(3) 0.039(2) 0.043(2) -0.0044(15) -0.0088(19) -0.0048(16) _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 N1 1.466(6) . ? C1 C2 1.504(7) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O1 1.204(6) . ? C2 N2 1.385(6) . ? C3 O2 1.213(6) . ? C3 N1 1.355(6) . ? C3 N2 1.388(6) . ? C4 N3 1.273(6) . ? C4 C5 1.436(7) . ? C4 H4A 0.9500 . ? C5 O3 1.365(6) . ? C5 C6 1.366(7) . ? C6 C7 1.415(9) . ? C6 H6A 0.9500 . ? C7 C8 1.324(9) . ? C7 H7A 0.9500 . ? C8 O3 1.349(6) . ? C8 N4 1.439(8) . ? C9 O6 1.341(6) . ? C9 C14 1.390(6) . ? C9 C10 1.414(7) . ? C10 C11 1.363(7) . ? C10 O7 1.373(6) . ? C11 C12 1.411(7) . ? C11 H11A 0.9500 . ? C12 C13 1.391(7) . ? C12 C16 1.443(7) . ? C13 C14 1.369(7) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 O7 1.425(6) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 O8 1.217(6) . ? C16 H16A 0.9500 . ? C17 O9 1.341(6) . ? C17 C18 1.378(7) . ? C17 C22 1.439(6) . ? C18 C19 1.379(7) . ? C18 H18A 0.9500 . ? C19 C20 1.385(7) . ? C19 H19A 0.9500 . ? C20 C21 1.405(7) . ? C20 C24 1.450(7) . ? C21 C22 1.361(7) . ? C21 H21A 0.9500 . ? C22 O10 1.363(6) . ? C23 O10 1.441(6) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 O11 1.217(6) . ? C24 H24A 0.9500 . ? N1 N3 1.354(5) . ? N2 H2A 0.8800 . ? N4 O5 1.218(8) . ? N4 O4 1.235(7) . ? O6 H6 0.8400 . ? O9 H9 0.8400 . ? 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 N1 C1 C2 101.6(4) . . ? N1 C1 H1A 111.4 . . ? C2 C1 H1A 111.4 . . ? N1 C1 H1B 111.4 . . ? C2 C1 H1B 111.4 . . ? H1A C1 H1B 109.3 . . ? O1 C2 N2 125.5(4) . . ? O1 C2 C1 128.1(4) . . ? N2 C2 C1 106.4(4) . . ? O2 C3 N1 127.5(4) . . ? O2 C3 N2 126.2(4) . . ? N1 C3 N2 106.3(4) . . ? N3 C4 C5 118.9(4) . . ? N3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? O3 C5 C6 110.6(4) . . ? O3 C5 C4 115.9(4) . . ? C6 C5 C4 133.5(5) . . ? C5 C6 C7 105.4(5) . . ? C5 C6 H6A 127.3 . . ? C7 C6 H6A 127.3 . . ? C8 C7 C6 106.5(5) . . ? C8 C7 H7A 126.7 . . ? C6 C7 H7A 126.7 . . ? C7 C8 O3 112.5(5) . . ? C7 C8 N4 132.5(5) . . ? O3 C8 N4 114.9(5) . . ? O6 C9 C14 119.3(4) . . ? O6 C9 C10 121.6(4) . . ? C14 C9 C10 119.1(4) . . ? C11 C10 O7 126.5(4) . . ? C11 C10 C9 120.0(4) . . ? O7 C10 C9 113.6(4) . . ? C10 C11 C12 120.7(4) . . ? C10 C11 H11A 119.7 . . ? C12 C11 H11A 119.7 . . ? C13 C12 C11 118.7(5) . . ? C13 C12 C16 120.9(4) . . ? C11 C12 C16 120.3(4) . . ? C14 C13 C12 120.9(4) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C13 C14 C9 120.6(5) . . ? C13 C14 H14A 119.7 . . ? C9 C14 H14A 119.7 . . ? O7 C15 H15A 109.5 . . ? O7 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O7 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O8 C16 C12 124.4(5) . . ? O8 C16 H16A 117.8 . . ? C12 C16 H16A 117.8 . . ? O9 C17 C18 124.0(4) . . ? O9 C17 C22 116.8(4) . . ? C18 C17 C22 119.2(4) . . ? C17 C18 C19 120.6(4) . . ? C17 C18 H18A 119.7 . . ? C19 C18 H18A 119.7 . . ? C18 C19 C20 120.4(5) . . ? C18 C19 H19A 119.8 . . ? C20 C19 H19A 119.8 . . ? C19 C20 C21 119.8(4) . . ? C19 C20 C24 118.7(5) . . ? C21 C20 C24 121.4(4) . . ? C22 C21 C20 120.4(4) . . ? C22 C21 H21A 119.8 . . ? C20 C21 H21A 119.8 . . ? C21 C22 O10 126.5(4) . . ? C21 C22 C17 119.5(4) . . ? O10 C22 C17 113.9(4) . . ? O10 C23 H23A 109.5 . . ? O10 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O10 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O11 C24 C20 125.9(5) . . ? O11 C24 H24A 117.0 . . ? C20 C24 H24A 117.0 . . ? N3 N1 C3 119.9(4) . . ? N3 N1 C1 126.9(4) . . ? C3 N1 C1 112.8(4) . . ? C2 N2 C3 112.6(4) . . ? C2 N2 H2A 123.7 . . ? C3 N2 H2A 123.7 . . ? C4 N3 N1 117.4(4) . . ? O5 N4 O4 126.4(6) . . ? O5 N4 C8 119.1(5) . . ? O4 N4 C8 114.4(7) . . ? C8 O3 C5 105.0(4) . . ? C9 O6 H6 109.5 . . ? C10 O7 C15 116.5(4) . . ? C17 O9 H9 109.5 . . ? C22 O10 C23 115.7(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 N1 C1 C2 O1 -176.3(5) . . . . ? N1 C1 C2 N2 4.1(5) . . . . ? N3 C4 C5 O3 179.2(5) . . . . ? N3 C4 C5 C6 -2.2(10) . . . . ? O3 C5 C6 C7 0.9(7) . . . . ? C4 C5 C6 C7 -177.7(6) . . . . ? C5 C6 C7 C8 -0.8(7) . . . . ? C6 C7 C8 O3 0.5(7) . . . . ? C6 C7 C8 N4 178.3(6) . . . . ? O6 C9 C10 C11 179.1(5) . . . . ? C14 C9 C10 C11 -1.1(8) . . . . ? O6 C9 C10 O7 -1.2(7) . . . . ? C14 C9 C10 O7 178.6(5) . . . . ? O7 C10 C11 C12 -179.5(5) . . . . ? C9 C10 C11 C12 0.1(8) . . . . ? C10 C11 C12 C13 0.9(8) . . . . ? C10 C11 C12 C16 -177.7(5) . . . . ? C11 C12 C13 C14 -0.8(8) . . . . ? C16 C12 C13 C14 177.8(5) . . . . ? C12 C13 C14 C9 -0.2(9) . . . . ? O6 C9 C14 C13 -179.0(5) . . . . ? C10 C9 C14 C13 1.1(8) . . . . ? C13 C12 C16 O8 -2.2(9) . . . . ? C11 C12 C16 O8 176.3(5) . . . . ? O9 C17 C18 C19 -178.1(5) . . . . ? C22 C17 C18 C19 0.1(8) . . . . ? C17 C18 C19 C20 -0.5(8) . . . . ? C18 C19 C20 C21 0.2(8) . . . . ? C18 C19 C20 C24 179.0(5) . . . . ? C19 C20 C21 C22 0.5(8) . . . . ? C24 C20 C21 C22 -178.3(5) . . . . ? C20 C21 C22 O10 178.5(5) . . . . ? C20 C21 C22 C17 -0.9(8) . . . . ? O9 C17 C22 C21 178.9(5) . . . . ? C18 C17 C22 C21 0.6(8) . . . . ? O9 C17 C22 O10 -0.6(7) . . . . ? C18 C17 C22 O10 -178.9(5) . . . . ? C19 C20 C24 O11 -179.4(5) . . . . ? C21 C20 C24 O11 -0.6(9) . . . . ? O2 C3 N1 N3 -3.5(9) . . . . ? N2 C3 N1 N3 176.6(4) . . . . ? O2 C3 N1 C1 -176.5(5) . . . . ? N2 C3 N1 C1 3.6(6) . . . . ? C2 C1 N1 N3 -177.2(5) . . . . ? C2 C1 N1 C3 -4.8(6) . . . . ? O1 C2 N2 C3 178.1(5) . . . . ? C1 C2 N2 C3 -2.3(6) . . . . ? O2 C3 N2 C2 179.4(5) . . . . ? N1 C3 N2 C2 -0.7(6) . . . . ? C5 C4 N3 N1 178.2(4) . . . . ? C3 N1 N3 C4 -174.8(5) . . . . ? C1 N1 N3 C4 -2.9(8) . . . . ? C7 C8 N4 O5 -179.8(7) . . . . ? O3 C8 N4 O5 -2.1(8) . . . . ? C7 C8 N4 O4 1.0(10) . . . . ? O3 C8 N4 O4 178.7(5) . . . . ? C7 C8 O3 C5 0.0(6) . . . . ? N4 C8 O3 C5 -178.2(5) . . . . ? C6 C5 O3 C8 -0.5(6) . . . . ? C4 C5 O3 C8 178.3(5) . . . . ? C11 C10 O7 C15 0.4(8) . . . . ? C9 C10 O7 C15 -179.3(5) . . . . ? C21 C22 O10 C23 4.0(8) . . . . ? C17 C22 O10 C23 -176.5(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 H2A O8 0.88 1.89 2.774(5) 177.1 3_667 O6 H6 O11 0.84 1.92 2.633(5) 142.0 1_455 O9 H9 O2 0.84 2.05 2.874(5) 166.3 4_565 _diffrn_measured_fraction_theta_max 0.874 _diffrn_reflns_theta_full 65.07 _diffrn_measured_fraction_theta_full 0.874 _refine_diff_density_max 0.590 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.099