# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_NF-Pyridine(1:1) _database_code_depnum_ccdc_archive 'CCDC 847324' #TrackingRef '7490_web_deposit_cif_file_0_VenuR.Vangala_1317865493.NF-solvates-salt CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Nitrofurantoin-pyridine(1:1)' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 N5 O5' _chemical_formula_weight 317.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P - 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3012(17) _cell_length_b 12.940(3) _cell_length_c 14.208(3) _cell_angle_alpha 111.01(3) _cell_angle_beta 96.22(3) _cell_angle_gamma 91.11(3) _cell_volume 1413.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 3563 _cell_measurement_theta_min 2.4730 _cell_measurement_theta_max 31.0943 _exptl_crystal_description Hexagon _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9499 _exptl_absorpt_correction_T_max 0.9871 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn CCD area deterctor' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16779 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.25 _reflns_number_total 5029 _reflns_number_gt 4614 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0840P)^2^+0.8497P] 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 5029 _refine_ls_number_parameters 503 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0792 _refine_ls_R_factor_gt 0.0721 _refine_ls_wR_factor_ref 0.1831 _refine_ls_wR_factor_gt 0.1772 _refine_ls_goodness_of_fit_ref 1.209 _refine_ls_restrained_S_all 1.209 _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 O6 O 0.4024(2) 0.38652(15) 0.24393(14) 0.0306(5) Uani 1 1 d . . . O9 O 0.8206(3) 0.33348(16) 0.49357(15) 0.0370(5) Uani 1 1 d . . . O10 O 0.9663(2) 0.68471(16) 0.71773(15) 0.0371(5) Uani 1 1 d . . . O7 O 0.2787(3) 0.18906(16) 0.12514(16) 0.0403(5) Uani 1 1 d . . . N8 N 0.9272(3) 0.49990(19) 0.61749(18) 0.0303(5) Uani 1 1 d . . . N7 N 0.7407(3) 0.50551(18) 0.49528(17) 0.0290(5) Uani 1 1 d . . . N6 N 0.6303(3) 0.46468(19) 0.41025(17) 0.0299(5) Uani 1 1 d . . . C15 C 0.9021(3) 0.6105(2) 0.6420(2) 0.0306(6) Uani 1 1 d . . . N5 N 0.2231(3) 0.2670(2) 0.10515(19) 0.0378(6) Uani 1 1 d . . . C14 C 0.8271(3) 0.4339(2) 0.5307(2) 0.0298(6) Uani 1 1 d . . . C13 C 0.5605(3) 0.5364(2) 0.3782(2) 0.0292(6) Uani 1 1 d . . . O8 O 0.1153(3) 0.25846(19) 0.03541(18) 0.0534(7) Uani 1 1 d . . . C11 C 0.2510(4) 0.4759(2) 0.1586(2) 0.0322(6) Uani 1 1 d . . . C16 C 0.7809(3) 0.6209(2) 0.5585(2) 0.0295(6) Uani 1 1 d . . . C10 C 0.3530(3) 0.5557(2) 0.2406(2) 0.0312(6) Uani 1 1 d . . . C12 C 0.2877(3) 0.3773(2) 0.1654(2) 0.0315(6) Uani 1 1 d . . . C9 C 0.4414(3) 0.4988(2) 0.2896(2) 0.0290(6) Uani 1 1 d . . . O1 O 0.0273(2) 0.88457(15) 0.24404(15) 0.0308(5) Uani 1 1 d . . . O3 O 0.2611(3) 0.76214(17) 0.05047(16) 0.0410(5) Uani 1 1 d . . . O5 O -0.4013(2) 1.17907(16) 0.69378(16) 0.0364(5) Uani 1 1 d . . . O2 O 0.1152(3) 0.68919(16) 0.13307(16) 0.0391(5) Uani 1 1 d . . . N3 N -0.2346(3) 1.00064(18) 0.48414(18) 0.0297(5) Uani 1 1 d . . . O4 O -0.2963(3) 0.82840(15) 0.49376(16) 0.0373(5) Uani 1 1 d . . . N4 N -0.3756(3) 0.99363(19) 0.60636(18) 0.0309(5) Uani 1 1 d . . . N2 N -0.1501(3) 0.96099(19) 0.40328(17) 0.0301(5) Uani 1 1 d . . . N1 N 0.1668(3) 0.76810(19) 0.11361(18) 0.0328(5) Uani 1 1 d . . . C5 C -0.0932(3) 1.0323(2) 0.3692(2) 0.0300(6) Uani 1 1 d . . . C7 C -0.3539(3) 1.1046(2) 0.6243(2) 0.0291(6) Uani 1 1 d . . . C6 C -0.3013(3) 0.9287(2) 0.5242(2) 0.0295(6) Uani 1 1 d . . . C4 C 0.1170(3) 0.8763(2) 0.1673(2) 0.0296(6) Uani 1 1 d . . . C1 C -0.0020(3) 0.9953(2) 0.2841(2) 0.0295(6) Uani 1 1 d . . . C2 C 0.0679(3) 1.0528(2) 0.2329(2) 0.0326(6) Uani 1 1 d . . . C8 C -0.2592(4) 1.1163(2) 0.5426(2) 0.0306(6) Uani 1 1 d . . . C3 C 0.1451(4) 0.9741(2) 0.1563(2) 0.0327(6) Uani 1 1 d . . . N10 N 0.5364(3) 0.0729(2) 0.26492(18) 0.0326(5) Uani 1 1 d . . . C22 C 0.5650(4) -0.0077(3) 0.1783(2) 0.0370(7) Uani 1 1 d . . . C26 C 0.5939(3) 0.1761(2) 0.2814(2) 0.0345(7) Uani 1 1 d . . . C23 C 0.6502(4) 0.0122(3) 0.1075(3) 0.0458(8) Uani 1 1 d . . . C25 C 0.6799(4) 0.2020(3) 0.2144(3) 0.0387(7) Uani 1 1 d . . . C24 C 0.7082(4) 0.1196(3) 0.1267(3) 0.0474(8) Uani 1 1 d . . . N9 N 0.8718(3) 0.5686(2) 0.25249(19) 0.0333(6) Uani 1 1 d . . . C20 C 0.7204(4) 0.7015(3) 0.2054(3) 0.0388(7) Uani 1 1 d . . . C21 C 0.8227(4) 0.6717(2) 0.2732(2) 0.0338(7) Uani 1 1 d . . . C17 C 0.8181(4) 0.4927(3) 0.1608(2) 0.0352(7) Uani 1 1 d . . . C18 C 0.7164(4) 0.5162(3) 0.0892(2) 0.0406(7) Uani 1 1 d . . . C19 C 0.6666(4) 0.6228(3) 0.1122(3) 0.0432(8) Uani 1 1 d . . . H4 H -0.429(4) 0.967(3) 0.659(3) 0.046(9) Uiso 1 1 d . . . H8 H 0.996(4) 0.471(3) 0.660(3) 0.051(10) Uiso 1 1 d . . . H11 H 0.169(4) 0.484(2) 0.107(2) 0.027(7) Uiso 1 1 d . . . H2 H 0.064(4) 1.130(3) 0.247(2) 0.033(8) Uiso 1 1 d . . . H22 H 0.524(4) -0.082(3) 0.173(3) 0.057(11) Uiso 1 1 d . . . H10 H 0.356(4) 0.630(3) 0.258(2) 0.035(8) Uiso 1 1 d . . . H13 H 0.575(3) 0.614(2) 0.409(2) 0.022(7) Uiso 1 1 d . . . H5 H -0.109(3) 1.112(2) 0.3984(19) 0.019(7) Uiso 1 1 d . . . H18 H 0.685(4) 0.458(3) 0.022(3) 0.041(9) Uiso 1 1 d . . . H16B H 0.829(4) 0.662(3) 0.518(2) 0.037(8) Uiso 1 1 d . . . H17 H 0.859(4) 0.420(3) 0.149(2) 0.038(8) Uiso 1 1 d . . . H8C H -0.325(4) 1.155(3) 0.506(2) 0.038(8) Uiso 1 1 d . . . H16A H 0.681(4) 0.653(3) 0.587(2) 0.035(8) Uiso 1 1 d . . . H21 H 0.863(4) 0.724(3) 0.340(2) 0.035(8) Uiso 1 1 d . . . H3 H 0.212(4) 0.984(3) 0.106(2) 0.036(8) Uiso 1 1 d . . . H26 H 0.565(4) 0.233(3) 0.347(2) 0.034(8) Uiso 1 1 d . . . H8B H -0.160(4) 1.157(3) 0.575(2) 0.041(9) Uiso 1 1 d . . . H20 H 0.682(4) 0.771(3) 0.227(3) 0.052(10) Uiso 1 1 d . . . H19 H 0.600(5) 0.641(3) 0.062(3) 0.060(11) Uiso 1 1 d . . . H24 H 0.777(5) 0.134(3) 0.078(3) 0.064(11) Uiso 1 1 d . . . H25 H 0.714(5) 0.276(3) 0.232(3) 0.055(10) Uiso 1 1 d . . . H23 H 0.672(5) -0.048(4) 0.047(3) 0.078(13) 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 O6 0.0350(10) 0.0240(10) 0.0322(11) 0.0108(8) -0.0003(8) 0.0015(8) O9 0.0480(12) 0.0227(11) 0.0373(12) 0.0088(9) -0.0007(9) 0.0024(9) O10 0.0390(11) 0.0274(11) 0.0388(12) 0.0065(9) -0.0015(9) -0.0013(9) O7 0.0500(13) 0.0240(11) 0.0454(13) 0.0128(9) -0.0012(10) 0.0016(9) N8 0.0332(12) 0.0249(13) 0.0322(13) 0.0102(10) 0.0021(10) 0.0033(10) N7 0.0317(12) 0.0242(12) 0.0306(13) 0.0105(10) 0.0001(10) 0.0019(9) N6 0.0300(12) 0.0285(13) 0.0314(13) 0.0111(10) 0.0042(10) 0.0000(9) C15 0.0287(14) 0.0283(15) 0.0337(15) 0.0095(12) 0.0056(11) -0.0001(11) N5 0.0438(14) 0.0310(14) 0.0362(14) 0.0113(11) -0.0005(11) -0.0016(11) C14 0.0325(14) 0.0245(15) 0.0322(15) 0.0100(12) 0.0047(11) 0.0011(11) C13 0.0315(14) 0.0267(15) 0.0315(15) 0.0125(12) 0.0063(11) -0.0008(11) O8 0.0646(15) 0.0405(13) 0.0471(14) 0.0147(11) -0.0209(12) -0.0083(11) C11 0.0357(15) 0.0310(15) 0.0324(15) 0.0150(12) 0.0024(12) 0.0012(12) C16 0.0316(14) 0.0222(14) 0.0335(15) 0.0093(12) 0.0025(12) 0.0011(11) C10 0.0376(15) 0.0219(15) 0.0350(16) 0.0109(12) 0.0056(12) 0.0008(12) C12 0.0359(15) 0.0280(15) 0.0313(15) 0.0123(12) 0.0017(12) -0.0010(12) C9 0.0304(14) 0.0227(14) 0.0352(15) 0.0112(12) 0.0078(11) 0.0005(11) O1 0.0322(10) 0.0254(10) 0.0363(11) 0.0137(8) 0.0020(8) 0.0016(8) O3 0.0500(13) 0.0357(12) 0.0390(12) 0.0124(9) 0.0155(10) 0.0071(10) O5 0.0394(11) 0.0275(11) 0.0408(12) 0.0094(9) 0.0087(9) 0.0056(9) O2 0.0494(12) 0.0254(11) 0.0454(13) 0.0158(9) 0.0082(10) 0.0031(9) N3 0.0341(12) 0.0233(12) 0.0327(13) 0.0109(10) 0.0055(10) 0.0029(9) O4 0.0503(12) 0.0215(11) 0.0393(12) 0.0100(9) 0.0066(9) 0.0018(9) N4 0.0314(12) 0.0284(13) 0.0341(13) 0.0133(10) 0.0029(10) 0.0015(9) N2 0.0294(12) 0.0298(13) 0.0313(13) 0.0121(10) 0.0016(10) 0.0030(10) N1 0.0386(13) 0.0274(13) 0.0327(13) 0.0113(10) 0.0044(10) 0.0034(10) C5 0.0271(14) 0.0258(15) 0.0370(16) 0.0124(12) -0.0013(11) 0.0034(11) C7 0.0298(14) 0.0242(14) 0.0319(15) 0.0097(12) -0.0009(11) 0.0024(11) C6 0.0323(14) 0.0251(15) 0.0302(15) 0.0106(11) -0.0012(11) 0.0006(11) C4 0.0301(14) 0.0272(15) 0.0310(15) 0.0112(12) 0.0000(11) 0.0005(11) C1 0.0292(14) 0.0251(14) 0.0349(15) 0.0130(12) -0.0001(11) 0.0038(11) C2 0.0340(15) 0.0263(16) 0.0389(17) 0.0146(13) 0.0006(12) 0.0038(12) C8 0.0327(15) 0.0219(14) 0.0366(16) 0.0104(12) 0.0025(12) 0.0016(11) C3 0.0363(15) 0.0296(15) 0.0347(16) 0.0155(12) 0.0014(12) -0.0008(12) N10 0.0338(13) 0.0306(13) 0.0356(13) 0.0148(11) 0.0038(10) 0.0005(10) C22 0.0384(16) 0.0303(16) 0.0387(17) 0.0096(13) 0.0000(13) 0.0014(13) C26 0.0331(15) 0.0308(16) 0.0380(17) 0.0123(13) -0.0016(12) 0.0012(12) C23 0.0482(19) 0.049(2) 0.0362(18) 0.0092(15) 0.0082(14) 0.0110(15) C25 0.0339(15) 0.0338(17) 0.054(2) 0.0224(15) 0.0047(14) -0.0010(13) C24 0.0421(18) 0.061(2) 0.051(2) 0.0322(18) 0.0118(15) 0.0101(16) N9 0.0341(13) 0.0293(13) 0.0378(14) 0.0142(11) 0.0029(10) 0.0007(10) C20 0.0360(16) 0.0321(17) 0.0505(19) 0.0168(15) 0.0071(14) 0.0069(13) C21 0.0369(15) 0.0293(16) 0.0329(16) 0.0079(13) 0.0071(12) -0.0014(12) C17 0.0387(16) 0.0273(16) 0.0381(17) 0.0100(13) 0.0059(13) 0.0009(12) C18 0.0426(17) 0.0388(18) 0.0335(17) 0.0065(14) -0.0001(13) -0.0044(14) C19 0.0387(17) 0.049(2) 0.0461(19) 0.0245(16) -0.0009(14) 0.0004(14) _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 O6 C12 1.354(3) . ? O6 C9 1.378(3) . ? O9 C14 1.212(3) . ? O10 C15 1.216(3) . ? O7 N5 1.227(3) . ? N8 C15 1.373(4) . ? N8 C14 1.391(4) . ? N8 H8 0.96(4) . ? N7 N6 1.365(3) . ? N7 C14 1.382(4) . ? N7 C16 1.450(3) . ? N6 C13 1.293(4) . ? C15 C16 1.516(4) . ? N5 O8 1.233(3) . ? N5 C12 1.433(4) . ? C13 C9 1.440(4) . ? C13 H13 0.94(3) . ? C11 C12 1.352(4) . ? C11 C10 1.425(4) . ? C11 H11 0.98(3) . ? C16 H16B 1.02(3) . ? C16 H16A 0.99(3) . ? C10 C9 1.357(4) . ? C10 H10 0.91(3) . ? O1 C4 1.360(3) . ? O1 C1 1.376(3) . ? O3 N1 1.236(3) . ? O5 C7 1.214(3) . ? O2 N1 1.230(3) . ? N3 N2 1.357(3) . ? N3 C6 1.388(4) . ? N3 C8 1.459(4) . ? O4 C6 1.215(3) . ? N4 C7 1.370(4) . ? N4 C6 1.386(4) . ? N4 H4 1.06(4) . ? N2 C5 1.288(4) . ? N1 C4 1.428(4) . ? C5 C1 1.437(4) . ? C5 H5 0.98(3) . ? C7 C8 1.519(4) . ? C4 C3 1.348(4) . ? C1 C2 1.372(4) . ? C2 C3 1.419(4) . ? C2 H2 0.95(3) . ? C8 H8C 0.98(3) . ? C8 H8B 0.95(4) . ? C3 H3 0.99(3) . ? N10 C26 1.339(4) . ? N10 C22 1.346(4) . ? C22 C23 1.383(5) . ? C22 H22 0.98(4) . ? C26 C25 1.378(4) . ? C26 H26 1.02(3) . ? C23 C24 1.383(5) . ? C23 H23 0.97(4) . ? C25 C24 1.366(5) . ? C25 H25 0.93(4) . ? C24 H24 1.01(4) . ? N9 C21 1.340(4) . ? N9 C17 1.341(4) . ? C20 C19 1.370(5) . ? C20 C21 1.379(4) . ? C20 H20 0.92(4) . ? C21 H21 0.97(3) . ? C17 C18 1.373(5) . ? C17 H17 0.97(3) . ? C18 C19 1.382(5) . ? C18 H18 0.99(3) . ? C19 H19 0.95(4) . ? 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 O6 C9 104.3(2) . . ? C15 N8 C14 112.0(2) . . ? C15 N8 H8 123(2) . . ? C14 N8 H8 124(2) . . ? N6 N7 C14 120.2(2) . . ? N6 N7 C16 127.4(2) . . ? C14 N7 C16 112.5(2) . . ? C13 N6 N7 116.8(2) . . ? O10 C15 N8 125.1(3) . . ? O10 C15 C16 127.6(3) . . ? N8 C15 C16 107.3(2) . . ? O7 N5 O8 125.1(2) . . ? O7 N5 C12 118.8(2) . . ? O8 N5 C12 116.1(2) . . ? O9 C14 N7 127.5(3) . . ? O9 C14 N8 126.1(3) . . ? N7 C14 N8 106.4(2) . . ? N6 C13 C9 119.6(3) . . ? N6 C13 H13 126.8(17) . . ? C9 C13 H13 113.6(17) . . ? C12 C11 C10 104.4(3) . . ? C12 C11 H11 123.6(17) . . ? C10 C11 H11 131.9(17) . . ? N7 C16 C15 101.6(2) . . ? N7 C16 H16B 110.7(17) . . ? C15 C16 H16B 112.8(18) . . ? N7 C16 H16A 108.1(18) . . ? C15 C16 H16A 110.4(18) . . ? H16B C16 H16A 113(2) . . ? C9 C10 C11 106.9(3) . . ? C9 C10 H10 127(2) . . ? C11 C10 H10 126(2) . . ? C11 C12 O6 113.5(3) . . ? C11 C12 N5 130.6(3) . . ? O6 C12 N5 115.9(2) . . ? C10 C9 O6 110.8(2) . . ? C10 C9 C13 131.2(3) . . ? O6 C9 C13 117.9(2) . . ? C4 O1 C1 104.5(2) . . ? N2 N3 C6 120.3(2) . . ? N2 N3 C8 127.6(2) . . ? C6 N3 C8 112.1(2) . . ? C7 N4 C6 112.4(2) . . ? C7 N4 H4 120.2(18) . . ? C6 N4 H4 126.8(18) . . ? C5 N2 N3 117.0(2) . . ? O2 N1 O3 125.1(2) . . ? O2 N1 C4 119.0(2) . . ? O3 N1 C4 115.9(2) . . ? N2 C5 C1 119.5(3) . . ? N2 C5 H5 123.5(16) . . ? C1 C5 H5 117.1(16) . . ? O5 C7 N4 125.5(3) . . ? O5 C7 C8 127.0(3) . . ? N4 C7 C8 107.5(2) . . ? O4 C6 N4 126.3(3) . . ? O4 C6 N3 127.1(3) . . ? N4 C6 N3 106.6(2) . . ? C3 C4 O1 113.1(3) . . ? C3 C4 N1 131.2(3) . . ? O1 C4 N1 115.7(2) . . ? C2 C1 O1 110.6(2) . . ? C2 C1 C5 130.9(3) . . ? O1 C1 C5 118.4(2) . . ? C1 C2 C3 106.4(3) . . ? C1 C2 H2 125.8(19) . . ? C3 C2 H2 127.8(19) . . ? N3 C8 C7 101.4(2) . . ? N3 C8 H8C 115.2(19) . . ? C7 C8 H8C 107.9(19) . . ? N3 C8 H8B 112(2) . . ? C7 C8 H8B 108(2) . . ? H8C C8 H8B 112(3) . . ? C4 C3 C2 105.3(3) . . ? C4 C3 H3 123.8(18) . . ? C2 C3 H3 130.8(18) . . ? C26 N10 C22 117.4(3) . . ? N10 C22 C23 122.8(3) . . ? N10 C22 H22 113(2) . . ? C23 C22 H22 124(2) . . ? N10 C26 C25 122.9(3) . . ? N10 C26 H26 113.3(18) . . ? C25 C26 H26 123.7(18) . . ? C24 C23 C22 118.5(3) . . ? C24 C23 H23 121(3) . . ? C22 C23 H23 121(3) . . ? C24 C25 C26 119.1(3) . . ? C24 C25 H25 124(2) . . ? C26 C25 H25 117(2) . . ? C25 C24 C23 119.2(3) . . ? C25 C24 H24 122(2) . . ? C23 C24 H24 119(2) . . ? C21 N9 C17 117.3(3) . . ? C19 C20 C21 118.9(3) . . ? C19 C20 H20 122(2) . . ? C21 C20 H20 119(2) . . ? N9 C21 C20 123.0(3) . . ? N9 C21 H21 114.9(19) . . ? C20 C21 H21 122.1(19) . . ? N9 C17 C18 123.1(3) . . ? N9 C17 H17 113.9(19) . . ? C18 C17 H17 123.0(19) . . ? C17 C18 C19 118.8(3) . . ? C17 C18 H18 119.7(19) . . ? C19 C18 H18 121.5(19) . . ? C20 C19 C18 119.0(3) . . ? C20 C19 H19 121(2) . . ? C18 C19 H19 120(2) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.285 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.065 data_NF-2-Picoline(1:1) _database_code_depnum_ccdc_archive 'CCDC 847325' #TrackingRef '7490_web_deposit_cif_file_0_VenuR.Vangala_1317865493.NF-solvates-salt CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Nitrofurantoin and 2-Picoline(1:1)' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H6 N4 O5, C6 H7 N' _chemical_formula_sum 'C14 H13 N5 O5' _chemical_formula_weight 331.29 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 2 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 7.0324(14) _cell_length_b 22.647(4) _cell_length_c 10.031(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.38(2) _cell_angle_gamma 90.00 _cell_volume 1477.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 4799 _cell_measurement_theta_min 2.3728 _cell_measurement_theta_max 31.0261 _exptl_crystal_description Platelet _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9626 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn CCD area deterctor' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9055 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2594 _reflns_number_gt 2324 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0771P)^2^+0.8331P] 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 2594 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1595 _refine_ls_wR_factor_gt 0.1468 _refine_ls_goodness_of_fit_ref 1.174 _refine_ls_restrained_S_all 1.174 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1892(3) 0.33209(7) -0.26929(17) 0.0238(4) Uani 1 1 d . . . O2 O 0.0547(3) 0.35198(9) -0.63664(19) 0.0377(5) Uani 1 1 d . . . O3 O 0.0243(3) 0.27521(9) -0.5136(2) 0.0378(5) Uani 1 1 d . . . O4 O 0.5058(3) 0.27391(8) 0.50973(19) 0.0353(5) Uani 1 1 d . . . O5 O 0.6721(3) 0.44526(8) 0.33882(18) 0.0305(5) Uani 1 1 d . . . N1 N 0.0749(4) 0.32680(10) -0.5220(2) 0.0289(5) Uani 1 1 d . . . N2 N 0.4182(3) 0.38780(9) 0.0867(2) 0.0243(5) Uani 1 1 d . . . N3 N 0.4668(3) 0.36552(9) 0.2215(2) 0.0244(5) Uani 1 1 d . . . N4 N 0.6210(3) 0.36320(9) 0.4602(2) 0.0250(5) Uani 1 1 d . . . C1 C 0.2701(4) 0.37420(11) -0.1634(3) 0.0225(5) Uani 1 1 d . . . C2 C 0.2884(4) 0.42689(11) -0.2234(3) 0.0255(6) Uani 1 1 d . . . H2A H 0.3401 0.4627 -0.1732 0.031 Uiso 1 1 calc R . . C3 C 0.2164(4) 0.41836(11) -0.3732(3) 0.0278(6) Uani 1 1 d . . . H3A H 0.2093 0.4468 -0.4445 0.033 Uiso 1 1 calc R . . C4 C 0.1592(4) 0.36095(11) -0.3943(3) 0.0251(6) Uani 1 1 d . . . C5 C 0.3188(4) 0.35279(11) -0.0185(3) 0.0240(5) Uani 1 1 d . . . H5A H 0.2791 0.3144 -0.0012 0.029 Uiso 1 1 calc R . . C6 C 0.4158(4) 0.30767(11) 0.2621(3) 0.0263(6) Uani 1 1 d . . . H6B H 0.4752 0.2755 0.2234 0.032 Uiso 1 1 calc R . . H6A H 0.2652 0.3021 0.2290 0.032 Uiso 1 1 calc R . . C7 C 0.5163(4) 0.31103(11) 0.4255(3) 0.0270(6) Uani 1 1 d . . . C8 C 0.5960(4) 0.39746(11) 0.3394(3) 0.0239(6) Uani 1 1 d . . . H4A H 0.697(6) 0.3781(18) 0.558(5) 0.081(13) Uiso 1 1 d . . . C9 C 0.7863(4) 0.44632(11) 0.8045(3) 0.0253(6) Uani 1 1 d . . . C10 C 0.8031(4) 0.45521(12) 0.9463(3) 0.0292(6) Uani 1 1 d . . . H10A H 0.8042 0.4942 0.9817 0.035 Uiso 1 1 calc R . . C11 C 0.8179(4) 0.40736(13) 1.0350(3) 0.0306(6) Uani 1 1 d . . . H11A H 0.8317 0.4129 1.1321 0.037 Uiso 1 1 calc R . . C12 C 0.8123(4) 0.35109(12) 0.9796(3) 0.0299(6) Uani 1 1 d . . . H12A H 0.8240 0.3173 1.0383 0.036 Uiso 1 1 calc R . . C13 C 0.7895(4) 0.34501(11) 0.8376(3) 0.0271(6) Uani 1 1 d . . . H13A H 0.7818 0.3063 0.7992 0.033 Uiso 1 1 calc R . . C14 C 0.7785(4) 0.49631(11) 0.7051(3) 0.0311(6) Uani 1 1 d . . . H14A H 0.7762 0.5339 0.7530 0.047 Uiso 1 1 calc R . . H14B H 0.6542 0.4929 0.6173 0.047 Uiso 1 1 calc R . . H14C H 0.9001 0.4949 0.6799 0.047 Uiso 1 1 calc R . . N5 N 0.7778(3) 0.39153(9) 0.7507(2) 0.0261(5) 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 O1 0.0294(10) 0.0216(9) 0.0204(9) -0.0007(7) 0.0093(7) -0.0003(7) O2 0.0510(13) 0.0417(12) 0.0185(9) 0.0031(8) 0.0109(9) 0.0099(9) O3 0.0489(13) 0.0285(11) 0.0329(11) -0.0063(8) 0.0122(9) -0.0045(9) O4 0.0480(12) 0.0309(11) 0.0267(10) 0.0029(8) 0.0137(9) -0.0085(9) O5 0.0394(11) 0.0239(10) 0.0278(10) -0.0012(7) 0.0123(8) -0.0055(8) N1 0.0328(13) 0.0287(12) 0.0231(11) -0.0006(9) 0.0084(10) 0.0044(10) N2 0.0278(12) 0.0256(11) 0.0203(11) 0.0034(8) 0.0102(9) 0.0039(9) N3 0.0336(12) 0.0204(11) 0.0184(10) -0.0007(8) 0.0089(9) -0.0046(9) N4 0.0287(12) 0.0253(11) 0.0203(11) 0.0015(9) 0.0086(9) -0.0031(9) C1 0.0214(12) 0.0238(13) 0.0229(12) -0.0030(10) 0.0094(10) 0.0023(10) C2 0.0271(14) 0.0228(13) 0.0278(13) -0.0029(10) 0.0118(11) -0.0032(10) C3 0.0325(15) 0.0264(14) 0.0272(13) 0.0057(10) 0.0144(12) 0.0020(11) C4 0.0271(14) 0.0273(13) 0.0208(12) 0.0014(10) 0.0091(11) 0.0020(10) C5 0.0284(14) 0.0218(12) 0.0236(13) 0.0009(10) 0.0119(11) 0.0022(10) C6 0.0339(15) 0.0219(13) 0.0246(13) -0.0009(10) 0.0129(11) -0.0042(11) C7 0.0337(15) 0.0247(13) 0.0249(13) 0.0001(10) 0.0138(11) -0.0010(11) C8 0.0281(13) 0.0217(13) 0.0226(12) -0.0014(9) 0.0105(11) 0.0007(10) C9 0.0193(12) 0.0316(14) 0.0235(12) -0.0007(10) 0.0064(10) 0.0019(10) C10 0.0260(14) 0.0335(15) 0.0287(14) -0.0052(11) 0.0112(11) -0.0025(11) C11 0.0224(13) 0.0466(17) 0.0225(13) -0.0042(11) 0.0082(11) -0.0056(12) C12 0.0260(14) 0.0362(15) 0.0271(14) 0.0045(11) 0.0094(11) -0.0002(11) C13 0.0239(14) 0.0263(13) 0.0289(14) -0.0005(11) 0.0075(11) -0.0001(10) C14 0.0360(15) 0.0275(14) 0.0289(13) 0.0011(11) 0.0112(12) 0.0027(11) N5 0.0249(12) 0.0280(12) 0.0253(11) -0.0017(9) 0.0093(9) -0.0013(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.358(3) . ? O1 C1 1.379(3) . ? O2 N1 1.242(3) . ? O3 N1 1.234(3) . ? O4 C7 1.214(3) . ? O5 C8 1.209(3) . ? N1 C4 1.419(3) . ? N2 C5 1.292(3) . ? N2 N3 1.360(3) . ? N3 C8 1.389(3) . ? N3 C6 1.457(3) . ? N4 C7 1.365(3) . ? N4 C8 1.392(3) . ? N4 H4A 0.98(4) . ? C1 C2 1.364(3) . ? C1 C5 1.445(3) . ? C2 C3 1.405(4) . ? C2 H2A 0.9500 . ? C3 C4 1.354(4) . ? C3 H3A 0.9500 . ? C5 H5A 0.9500 . ? C6 C7 1.520(3) . ? C6 H6B 0.9900 . ? C6 H6A 0.9900 . ? C9 N5 1.345(3) . ? C9 C10 1.396(4) . ? C9 C14 1.495(4) . ? C10 C11 1.381(4) . ? C10 H10A 0.9500 . ? C11 C12 1.385(4) . ? C11 H11A 0.9500 . ? C12 C13 1.378(4) . ? C12 H12A 0.9500 . ? C13 N5 1.350(3) . ? C13 H13A 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 C4 O1 C1 104.58(19) . . ? O3 N1 O2 124.3(2) . . ? O3 N1 C4 119.1(2) . . ? O2 N1 C4 116.5(2) . . ? C5 N2 N3 116.0(2) . . ? N2 N3 C8 119.3(2) . . ? N2 N3 C6 128.0(2) . . ? C8 N3 C6 112.42(19) . . ? C7 N4 C8 112.5(2) . . ? C7 N4 H4A 126(2) . . ? C8 N4 H4A 121(2) . . ? C2 C1 O1 110.3(2) . . ? C2 C1 C5 135.3(2) . . ? O1 C1 C5 114.4(2) . . ? C1 C2 C3 107.2(2) . . ? C1 C2 H2A 126.4 . . ? C3 C2 H2A 126.4 . . ? C4 C3 C2 105.3(2) . . ? C4 C3 H3A 127.3 . . ? C2 C3 H3A 127.3 . . ? C3 C4 O1 112.7(2) . . ? C3 C4 N1 131.5(2) . . ? O1 C4 N1 115.9(2) . . ? N2 C5 C1 117.6(2) . . ? N2 C5 H5A 121.2 . . ? C1 C5 H5A 121.2 . . ? N3 C6 C7 101.16(19) . . ? N3 C6 H6B 111.5 . . ? C7 C6 H6B 111.5 . . ? N3 C6 H6A 111.5 . . ? C7 C6 H6A 111.5 . . ? H6B C6 H6A 109.4 . . ? O4 C7 N4 126.3(2) . . ? O4 C7 C6 126.1(2) . . ? N4 C7 C6 107.6(2) . . ? O5 C8 N3 127.6(2) . . ? O5 C8 N4 126.4(2) . . ? N3 C8 N4 106.0(2) . . ? N5 C9 C10 121.0(2) . . ? N5 C9 C14 116.5(2) . . ? C10 C9 C14 122.5(2) . . ? C11 C10 C9 120.0(2) . . ? C11 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? C10 C11 C12 118.7(2) . . ? C10 C11 H11A 120.7 . . ? C12 C11 H11A 120.7 . . ? C13 C12 C11 118.8(2) . . ? C13 C12 H12A 120.6 . . ? C11 C12 H12A 120.6 . . ? N5 C13 C12 123.0(2) . . ? N5 C13 H13A 118.5 . . ? C12 C13 H13A 118.5 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C9 N5 C13 118.6(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 C5 N2 N3 C8 171.8(2) . . . . ? C5 N2 N3 C6 -1.9(4) . . . . ? C4 O1 C1 C2 0.0(3) . . . . ? C4 O1 C1 C5 -178.9(2) . . . . ? O1 C1 C2 C3 0.1(3) . . . . ? C5 C1 C2 C3 178.5(3) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ? C2 C3 C4 O1 0.0(3) . . . . ? C2 C3 C4 N1 179.8(3) . . . . ? C1 O1 C4 C3 0.0(3) . . . . ? C1 O1 C4 N1 -179.8(2) . . . . ? O3 N1 C4 C3 -176.0(3) . . . . ? O2 N1 C4 C3 3.1(4) . . . . ? O3 N1 C4 O1 3.8(3) . . . . ? O2 N1 C4 O1 -177.1(2) . . . . ? N3 N2 C5 C1 -178.0(2) . . . . ? C2 C1 C5 N2 -6.8(4) . . . . ? O1 C1 C5 N2 171.7(2) . . . . ? N2 N3 C6 C7 179.4(2) . . . . ? C8 N3 C6 C7 5.4(3) . . . . ? C8 N4 C7 O4 -177.4(3) . . . . ? C8 N4 C7 C6 2.9(3) . . . . ? N3 C6 C7 O4 175.4(3) . . . . ? N3 C6 C7 N4 -4.8(3) . . . . ? N2 N3 C8 O5 1.5(4) . . . . ? C6 N3 C8 O5 176.1(2) . . . . ? N2 N3 C8 N4 -178.5(2) . . . . ? C6 N3 C8 N4 -3.9(3) . . . . ? C7 N4 C8 O5 -179.5(3) . . . . ? C7 N4 C8 N3 0.5(3) . . . . ? N5 C9 C10 C11 2.1(4) . . . . ? C14 C9 C10 C11 -177.4(2) . . . . ? C9 C10 C11 C12 -1.1(4) . . . . ? C10 C11 C12 C13 -0.8(4) . . . . ? C11 C12 C13 N5 1.8(4) . . . . ? C10 C9 N5 C13 -1.2(4) . . . . ? C14 C9 N5 C13 178.4(2) . . . . ? C12 C13 N5 C9 -0.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.271 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.061 data_NF-3-Picoline(1:1) _database_code_depnum_ccdc_archive 'CCDC 847326' #TrackingRef '7490_web_deposit_cif_file_0_VenuR.Vangala_1317865493.NF-solvates-salt CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Nitrofurantoin-3-picoline(1:1) ; _chemical_name_common ; Nitrofurantoin-3-picoline(1:1) ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 N5 O5' _chemical_formula_weight 331.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P - 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1489(12) _cell_length_b 7.4328(15) _cell_length_c 16.446(3) _cell_angle_alpha 85.35(3) _cell_angle_beta 85.97(3) _cell_angle_gamma 83.67(3) _cell_volume 743.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2162 _cell_measurement_theta_min 2.4899 _cell_measurement_theta_max 30.9240 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9628 _exptl_absorpt_correction_T_max 0.9750 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn CCD area deterctor' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7951 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 24.50 _reflns_number_total 2439 _reflns_number_gt 2337 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0879P)^2^+0.2944P] 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 2439 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1606 _refine_ls_wR_factor_gt 0.1577 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.157 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1697(2) 0.56192(19) 0.31212(9) 0.0311(4) Uani 1 1 d . . . N2 N 0.4619(3) 0.3560(2) 0.14522(11) 0.0282(4) Uani 1 1 d . . . O5 O 0.7614(2) 0.1649(2) 0.03720(10) 0.0348(4) Uani 1 1 d . . . N4 N 0.4859(3) 0.2174(2) -0.05424(11) 0.0287(4) Uani 1 1 d . . . N3 N 0.4184(3) 0.3160(2) 0.06949(11) 0.0293(4) Uani 1 1 d . . . O4 O 0.1642(3) 0.3228(2) -0.11358(10) 0.0380(4) Uani 1 1 d . . . C4 C 0.2487(4) 0.5977(3) 0.38330(13) 0.0312(5) Uani 1 1 d . . . C1 C 0.3503(3) 0.4973(3) 0.26501(13) 0.0286(5) Uani 1 1 d . . . C8 C 0.5779(3) 0.2241(3) 0.01984(13) 0.0278(5) Uani 1 1 d . . . O2 O -0.0984(3) 0.7102(3) 0.42543(12) 0.0532(5) Uani 1 1 d . . . O3 O 0.1643(3) 0.6965(2) 0.50894(11) 0.0517(5) Uani 1 1 d . . . C6 C 0.2158(3) 0.3684(3) 0.02903(13) 0.0287(5) Uani 1 1 d . . . H6A H 0.1765 0.5014 0.0265 0.034 Uiso 1 1 calc R . . H6B H 0.0927 0.3071 0.0566 0.034 Uiso 1 1 calc R . . N1 N 0.0929(3) 0.6729(2) 0.44254(12) 0.0371(5) Uani 1 1 d . . . C7 C 0.2778(3) 0.3021(3) -0.05581(13) 0.0297(5) Uani 1 1 d . . . C3 C 0.4689(4) 0.5615(3) 0.38356(14) 0.0336(5) Uani 1 1 d . . . H3A H 0.5596 0.5762 0.4265 0.040 Uiso 1 1 calc R . . C2 C 0.5349(4) 0.4971(3) 0.30635(14) 0.0334(5) Uani 1 1 d . . . H2A H 0.6808 0.4604 0.2868 0.040 Uiso 1 1 calc R . . C5 C 0.3058(3) 0.4471(3) 0.18600(13) 0.0293(5) Uani 1 1 d . . . H5A H 0.1665 0.4797 0.1644 0.035 Uiso 1 1 calc R . . N5 N 0.2924(3) 0.9390(2) 0.18684(11) 0.0317(5) Uani 1 1 d . . . C9 C 0.3899(4) 0.9565(3) 0.25532(14) 0.0314(5) Uani 1 1 d . . . H9A H 0.5392 0.9087 0.2583 0.038 Uiso 1 1 calc R . . C13 C 0.0825(4) 1.0084(3) 0.18195(15) 0.0347(5) Uani 1 1 d . . . H13A H 0.0111 0.9964 0.1336 0.042 Uiso 1 1 calc R . . C10 C 0.2873(4) 1.0400(3) 0.32254(13) 0.0343(5) Uani 1 1 d . . . C11 C 0.0694(4) 1.1101(3) 0.31519(16) 0.0399(6) Uani 1 1 d . . . H11A H -0.0094 1.1679 0.3594 0.048 Uiso 1 1 calc R . . C12 C -0.0329(4) 1.0962(3) 0.24437(16) 0.0414(6) Uani 1 1 d . . . H12A H -0.1805 1.1464 0.2388 0.050 Uiso 1 1 calc R . . C14 C 0.4049(5) 1.0539(4) 0.39803(16) 0.0504(7) Uani 1 1 d . . . H14A H 0.5557 0.9968 0.3909 0.076 Uiso 1 1 calc R . . H14B H 0.3291 0.9920 0.4448 0.076 Uiso 1 1 calc R . . H14C H 0.4067 1.1820 0.4078 0.076 Uiso 1 1 calc R . . H4 H 0.561(5) 0.166(4) -0.0985(19) 0.050(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0292(8) 0.0356(8) 0.0291(9) -0.0070(6) 0.0002(6) -0.0033(6) N2 0.0295(10) 0.0316(9) 0.0248(10) -0.0035(7) -0.0038(7) -0.0067(7) O5 0.0280(8) 0.0383(8) 0.0377(9) -0.0043(7) -0.0046(7) 0.0011(6) N4 0.0269(10) 0.0316(9) 0.0277(10) -0.0046(8) -0.0020(7) -0.0014(7) N3 0.0252(9) 0.0356(10) 0.0274(10) -0.0050(8) -0.0040(7) -0.0009(7) O4 0.0387(9) 0.0452(9) 0.0313(9) -0.0049(7) -0.0112(7) -0.0024(7) C4 0.0406(13) 0.0304(11) 0.0231(11) -0.0049(9) 0.0010(9) -0.0062(9) C1 0.0296(11) 0.0280(10) 0.0278(12) -0.0017(8) 0.0007(9) -0.0029(8) C8 0.0271(11) 0.0263(10) 0.0300(12) -0.0001(8) -0.0012(9) -0.0047(8) O2 0.0351(10) 0.0672(12) 0.0594(12) -0.0217(10) 0.0096(8) -0.0099(8) O3 0.0662(13) 0.0569(11) 0.0306(10) -0.0116(8) -0.0010(9) 0.0053(9) C6 0.0231(10) 0.0346(11) 0.0287(11) -0.0019(9) -0.0052(8) -0.0025(8) N1 0.0462(13) 0.0338(10) 0.0314(11) -0.0059(8) 0.0077(9) -0.0075(9) C7 0.0290(11) 0.0314(11) 0.0295(12) -0.0009(9) -0.0033(9) -0.0067(8) C3 0.0390(12) 0.0320(11) 0.0300(12) -0.0026(9) -0.0084(9) -0.0002(9) C2 0.0331(12) 0.0344(11) 0.0324(12) -0.0018(9) -0.0055(9) -0.0004(9) C5 0.0277(11) 0.0335(11) 0.0272(12) -0.0014(9) -0.0030(9) -0.0041(9) N5 0.0343(10) 0.0310(9) 0.0300(10) -0.0028(8) -0.0032(8) -0.0038(8) C9 0.0298(11) 0.0292(11) 0.0352(12) 0.0006(9) -0.0059(9) -0.0023(8) C13 0.0346(12) 0.0313(11) 0.0394(14) -0.0006(10) -0.0092(10) -0.0054(9) C10 0.0470(14) 0.0300(11) 0.0272(12) 0.0002(9) -0.0021(10) -0.0110(9) C11 0.0447(13) 0.0317(11) 0.0425(14) -0.0100(10) 0.0130(11) -0.0047(10) C12 0.0317(12) 0.0341(12) 0.0582(16) -0.0080(11) -0.0010(11) -0.0003(9) C14 0.0731(19) 0.0443(14) 0.0370(15) -0.0004(11) -0.0159(13) -0.0147(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 O1 C4 1.355(3) . ? O1 C1 1.373(3) . ? N2 C5 1.292(3) . ? N2 N3 1.355(2) . ? O5 C8 1.210(3) . ? N4 C7 1.363(3) . ? N4 C8 1.386(3) . ? N3 C8 1.387(3) . ? N3 C6 1.454(3) . ? O4 C7 1.208(3) . ? C4 C3 1.351(3) . ? C4 N1 1.421(3) . ? C1 C2 1.363(3) . ? C1 C5 1.433(3) . ? O2 N1 1.225(3) . ? O3 N1 1.238(3) . ? C6 C7 1.526(3) . ? C3 C2 1.411(3) . ? N5 C9 1.334(3) . ? N5 C13 1.341(3) . ? C9 C10 1.390(3) . ? C13 C12 1.374(4) . ? C10 C11 1.393(4) . ? C10 C14 1.496(3) . ? C11 C12 1.378(4) . ? 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 C4 O1 C1 105.12(16) . . ? C5 N2 N3 116.51(17) . . ? C7 N4 C8 113.07(19) . . ? N2 N3 C8 120.83(17) . . ? N2 N3 C6 126.58(17) . . ? C8 N3 C6 112.50(17) . . ? C3 C4 O1 112.58(19) . . ? C3 C4 N1 131.0(2) . . ? O1 C4 N1 116.33(19) . . ? C2 C1 O1 109.97(19) . . ? C2 C1 C5 134.8(2) . . ? O1 C1 C5 115.22(18) . . ? O5 C8 N4 127.0(2) . . ? O5 C8 N3 127.0(2) . . ? N4 C8 N3 106.01(17) . . ? N3 C6 C7 101.24(17) . . ? O2 N1 O3 124.7(2) . . ? O2 N1 C4 119.3(2) . . ? O3 N1 C4 116.0(2) . . ? O4 C7 N4 126.6(2) . . ? O4 C7 C6 126.3(2) . . ? N4 C7 C6 107.08(18) . . ? C4 C3 C2 105.1(2) . . ? C1 C2 C3 107.2(2) . . ? N2 C5 C1 117.66(19) . . ? C9 N5 C13 118.05(19) . . ? N5 C9 C10 124.2(2) . . ? N5 C13 C12 122.3(2) . . ? C9 C10 C11 116.0(2) . . ? C9 C10 C14 121.8(2) . . ? C11 C10 C14 122.2(2) . . ? C12 C11 C10 120.6(2) . . ? C13 C12 C11 118.8(2) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 24.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.292 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.060 data_NF-3-Picoline-H2O(1:1) _database_code_depnum_ccdc_archive 'CCDC 847327' #TrackingRef '7490_web_deposit_cif_file_0_VenuR.Vangala_1317865493.NF-solvates-salt CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1:1:1 solvate of nitrofurantoin, 3-picoline and water' ; _chemical_name_common '1:1:1 solvate of nitrofurantoin, 3-picoline and water' _chemical_melting_point ? _chemical_formula_moiety 'C8 H6 N4 O5, C6 H7 N, H2 O' _chemical_formula_sum 'C14 H15 N5 O6' _chemical_formula_weight 349.31 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 c' _symmetry_space_group_name_Hall 'P -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 15.268(6) _cell_length_b 6.4161(19) _cell_length_c 8.461(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.286(5) _cell_angle_gamma 90.00 _cell_volume 799.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2112 _cell_measurement_theta_min 2.4956 _cell_measurement_theta_max 30.8913 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.451 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9628 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn CCD area deterctor' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4817 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2644 _reflns_number_gt 2549 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.1718P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.8(9) _refine_ls_number_reflns 2644 _refine_ls_number_parameters 228 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0833 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.074 _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 O3 O 1.22755(11) 0.8693(3) 0.1873(2) 0.0356(4) Uani 1 1 d . . . O2 O 1.17191(11) 1.1326(2) 0.29283(19) 0.0315(4) Uani 1 1 d . . . O1 O 1.07210(9) 0.8835(2) 0.42003(17) 0.0239(3) Uani 1 1 d . . . O4 O 0.87446(11) 1.3274(2) 0.63797(19) 0.0291(3) Uani 1 1 d . . . O5 O 0.70306(11) 0.8761(2) 0.84914(19) 0.0294(4) Uani 1 1 d . . . N1 N 1.17973(13) 0.9455(3) 0.2697(2) 0.0260(4) Uani 1 1 d . . . N2 N 0.94260(11) 0.9403(3) 0.58028(19) 0.0223(4) Uani 1 1 d . . . N3 N 0.87601(12) 0.9667(3) 0.6575(2) 0.0237(4) Uani 1 1 d . . . N4 N 0.77493(12) 1.1415(3) 0.7511(2) 0.0239(4) Uani 1 1 d . . . H4A H 0.7477 1.2630 0.7839 0.029 Uiso 1 1 d R . . C1 C 1.03564(14) 0.7150(3) 0.4784(2) 0.0236(4) Uani 1 1 d . . . C2 C 1.07198(14) 0.5336(3) 0.4371(2) 0.0235(4) Uani 1 1 d . . . H2A H 1.0577 0.3959 0.4631 0.028 Uiso 1 1 calc R . . C3 C 1.13459(15) 0.5916(3) 0.3487(3) 0.0267(5) Uani 1 1 d . . . H3A H 1.1712 0.5021 0.3034 0.032 Uiso 1 1 calc R . . C4 C 1.13130(14) 0.8012(3) 0.3423(2) 0.0233(4) Uani 1 1 d . . . C5 C 0.96674(15) 0.7522(3) 0.5621(2) 0.0237(5) Uani 1 1 d . . . H5A H 0.9393 0.6391 0.6036 0.028 Uiso 1 1 calc R . . C6 C 0.84561(14) 1.1652(3) 0.6772(2) 0.0240(5) Uani 1 1 d . . . C7 C 0.75989(15) 0.9383(3) 0.7810(2) 0.0233(4) Uani 1 1 d . . . C8 C 0.82611(14) 0.8072(3) 0.7209(3) 0.0234(4) Uani 1 1 d . . . H8B H 0.8666 0.7273 0.8113 0.028 Uiso 1 1 calc R . . H8A H 0.7946 0.7098 0.6336 0.028 Uiso 1 1 calc R . . N5 N 0.55021(14) 0.2915(3) 0.9999(2) 0.0350(5) Uani 1 1 d . . . C9 C 0.49813(15) 0.4064(4) 1.0706(3) 0.0330(5) Uani 1 1 d . . . H9A H 0.5179 0.5436 1.1042 0.040 Uiso 1 1 calc R . . C10 C 0.41687(16) 0.3389(4) 1.0985(3) 0.0312(5) Uani 1 1 d . . . C11 C 0.39092(17) 0.1359(4) 1.0517(3) 0.0339(5) Uani 1 1 d . . . H11A H 0.3365 0.0811 1.0694 0.041 Uiso 1 1 calc R . . C12 C 0.44366(19) 0.0142(4) 0.9801(3) 0.0381(6) Uani 1 1 d . . . H12A H 0.4261 -0.1248 0.9477 0.046 Uiso 1 1 calc R . . C13 C 0.52282(17) 0.0970(4) 0.9558(3) 0.0360(5) Uani 1 1 d . . . H13A H 0.5591 0.0125 0.9058 0.043 Uiso 1 1 calc R . . C14 C 0.35916(18) 0.4824(4) 1.1679(3) 0.0432(6) Uani 1 1 d . . . H14A H 0.3291 0.4029 1.2374 0.065 Uiso 1 1 calc R . . H14B H 0.3132 0.5474 1.0782 0.065 Uiso 1 1 calc R . . H14C H 0.3974 0.5907 1.2333 0.065 Uiso 1 1 calc R . . O6 O 0.69221(11) 0.4382(2) 0.8854(2) 0.0342(4) Uani 1 1 d . . . H6B H 0.6376 0.3952 0.9276 0.051 Uiso 1 1 d R . . H6A H 0.6906 0.5655 0.8790 0.051 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0374(9) 0.0346(9) 0.0440(9) 0.0024(7) 0.0270(8) 0.0063(7) O2 0.0373(9) 0.0183(8) 0.0417(9) 0.0008(7) 0.0153(7) -0.0001(7) O1 0.0245(8) 0.0203(7) 0.0291(7) -0.0005(6) 0.0110(6) 0.0015(6) O4 0.0319(9) 0.0215(8) 0.0364(8) 0.0017(6) 0.0136(7) -0.0026(6) O5 0.0302(8) 0.0262(8) 0.0365(8) 0.0003(7) 0.0170(7) 0.0000(6) N1 0.0249(9) 0.0250(10) 0.0292(9) 0.0027(8) 0.0093(7) 0.0001(7) N2 0.0209(9) 0.0258(10) 0.0224(9) 0.0001(7) 0.0096(7) 0.0003(7) N3 0.0236(10) 0.0217(9) 0.0286(10) 0.0011(7) 0.0118(7) 0.0002(7) N4 0.0283(10) 0.0174(9) 0.0278(9) 0.0010(7) 0.0106(8) 0.0018(7) C1 0.0269(12) 0.0193(9) 0.0243(10) 0.0011(8) 0.0064(9) -0.0018(8) C2 0.0270(11) 0.0180(10) 0.0257(11) 0.0003(8) 0.0071(9) 0.0007(8) C3 0.0281(11) 0.0244(10) 0.0275(11) -0.0017(9) 0.0073(9) 0.0030(9) C4 0.0228(10) 0.0258(11) 0.0230(10) -0.0005(8) 0.0092(8) -0.0015(8) C5 0.0260(11) 0.0195(10) 0.0257(11) 0.0026(8) 0.0068(9) -0.0013(8) C6 0.0250(11) 0.0198(10) 0.0269(11) -0.0010(8) 0.0065(9) -0.0003(8) C7 0.0260(11) 0.0210(10) 0.0234(10) -0.0021(8) 0.0073(9) -0.0002(8) C8 0.0255(11) 0.0183(9) 0.0289(11) 0.0015(8) 0.0117(9) -0.0006(8) N5 0.0333(11) 0.0354(11) 0.0398(11) 0.0048(9) 0.0159(9) 0.0012(9) C9 0.0318(13) 0.0315(12) 0.0352(12) 0.0011(10) 0.0081(10) 0.0005(10) C10 0.0296(12) 0.0380(13) 0.0263(11) 0.0037(9) 0.0080(9) 0.0061(10) C11 0.0311(13) 0.0407(13) 0.0330(12) 0.0032(10) 0.0142(10) -0.0042(11) C12 0.0479(15) 0.0293(12) 0.0386(13) 0.0015(10) 0.0142(11) -0.0047(10) C13 0.0357(13) 0.0368(13) 0.0403(13) 0.0018(11) 0.0184(10) 0.0034(11) C14 0.0379(15) 0.0549(16) 0.0395(14) -0.0049(12) 0.0147(12) 0.0105(12) O6 0.0346(9) 0.0210(8) 0.0539(10) -0.0009(7) 0.0240(8) 0.0002(6) _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 O3 N1 1.236(2) . ? O2 N1 1.227(2) . ? O1 C4 1.357(3) . ? O1 C1 1.366(2) . ? O4 C6 1.210(3) . ? O5 C7 1.228(3) . ? N1 C4 1.421(3) . ? N2 C5 1.283(3) . ? N2 N3 1.356(2) . ? N3 C6 1.380(3) . ? N3 C8 1.460(3) . ? N4 C7 1.359(3) . ? N4 C6 1.391(3) . ? N4 H4A 0.9588 . ? C1 C2 1.373(3) . ? C1 C5 1.435(3) . ? C2 C3 1.410(3) . ? C2 H2A 0.9500 . ? C3 C4 1.346(3) . ? C3 H3A 0.9500 . ? C5 H5A 0.9500 . ? C7 C8 1.503(3) . ? C8 H8B 0.9900 . ? C8 H8A 0.9900 . ? N5 C9 1.336(3) . ? N5 C13 1.338(3) . ? C9 C10 1.392(3) . ? C9 H9A 0.9500 . ? C10 C11 1.388(3) . ? C10 C14 1.497(3) . ? C11 C12 1.373(3) . ? C11 H11A 0.9500 . ? C12 C13 1.385(4) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? O6 H6B 1.0278 . ? O6 H6A 0.8183 . ? 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 C4 O1 C1 104.73(16) . . ? O2 N1 O3 125.02(18) . . ? O2 N1 C4 119.01(18) . . ? O3 N1 C4 115.97(16) . . ? C5 N2 N3 116.81(17) . . ? N2 N3 C6 119.48(16) . . ? N2 N3 C8 128.27(17) . . ? C6 N3 C8 112.20(16) . . ? C7 N4 C6 112.18(18) . . ? C7 N4 H4A 128.2 . . ? C6 N4 H4A 119.3 . . ? O1 C1 C2 110.37(17) . . ? O1 C1 C5 117.91(18) . . ? C2 C1 C5 131.66(19) . . ? C1 C2 C3 106.69(18) . . ? C1 C2 H2A 126.7 . . ? C3 C2 H2A 126.7 . . ? C4 C3 C2 105.16(19) . . ? C4 C3 H3A 127.4 . . ? C2 C3 H3A 127.4 . . ? C3 C4 O1 113.05(19) . . ? C3 C4 N1 130.5(2) . . ? O1 C4 N1 116.41(18) . . ? N2 C5 C1 119.16(18) . . ? N2 C5 H5A 120.4 . . ? C1 C5 H5A 120.4 . . ? O4 C6 N3 127.02(18) . . ? O4 C6 N4 126.79(19) . . ? N3 C6 N4 106.19(16) . . ? O5 C7 N4 125.0(2) . . ? O5 C7 C8 126.8(2) . . ? N4 C7 C8 108.20(17) . . ? N3 C8 C7 101.22(16) . . ? N3 C8 H8B 111.5 . . ? C7 C8 H8B 111.5 . . ? N3 C8 H8A 111.5 . . ? C7 C8 H8A 111.5 . . ? H8B C8 H8A 109.3 . . ? C9 N5 C13 117.4(2) . . ? N5 C9 C10 124.5(2) . . ? N5 C9 H9A 117.7 . . ? C10 C9 H9A 117.7 . . ? C11 C10 C9 116.3(2) . . ? C11 C10 C14 122.4(2) . . ? C9 C10 C14 121.2(2) . . ? C12 C11 C10 120.2(2) . . ? C12 C11 H11A 119.9 . . ? C10 C11 H11A 119.9 . . ? C11 C12 C13 118.9(2) . . ? C11 C12 H12A 120.5 . . ? C13 C12 H12A 120.5 . . ? N5 C13 C12 122.5(2) . . ? N5 C13 H13A 118.7 . . ? C12 C13 H13A 118.7 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? H6B O6 H6A 106.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N2 N3 C6 -178.44(18) . . . . ? C5 N2 N3 C8 -1.3(3) . . . . ? C4 O1 C1 C2 0.1(2) . . . . ? C4 O1 C1 C5 -177.50(17) . . . . ? O1 C1 C2 C3 0.1(2) . . . . ? C5 C1 C2 C3 177.2(2) . . . . ? C1 C2 C3 C4 -0.3(2) . . . . ? C2 C3 C4 O1 0.3(2) . . . . ? C2 C3 C4 N1 179.7(2) . . . . ? C1 O1 C4 C3 -0.2(2) . . . . ? C1 O1 C4 N1 -179.70(16) . . . . ? O2 N1 C4 C3 -173.0(2) . . . . ? O3 N1 C4 C3 6.7(3) . . . . ? O2 N1 C4 O1 6.3(3) . . . . ? O3 N1 C4 O1 -174.00(18) . . . . ? N3 N2 C5 C1 178.78(17) . . . . ? O1 C1 C5 N2 -0.6(3) . . . . ? C2 C1 C5 N2 -177.5(2) . . . . ? N2 N3 C6 O4 -3.2(3) . . . . ? C8 N3 C6 O4 179.3(2) . . . . ? N2 N3 C6 N4 176.77(17) . . . . ? C8 N3 C6 N4 -0.8(2) . . . . ? C7 N4 C6 O4 -179.3(2) . . . . ? C7 N4 C6 N3 0.8(2) . . . . ? C6 N4 C7 O5 177.9(2) . . . . ? C6 N4 C7 C8 -0.4(2) . . . . ? N2 N3 C8 C7 -176.78(18) . . . . ? C6 N3 C8 C7 0.5(2) . . . . ? O5 C7 C8 N3 -178.4(2) . . . . ? N4 C7 C8 N3 0.0(2) . . . . ? C13 N5 C9 C10 -1.2(4) . . . . ? N5 C9 C10 C11 1.6(3) . . . . ? N5 C9 C10 C14 -175.7(2) . . . . ? C9 C10 C11 C12 -0.9(3) . . . . ? C14 C10 C11 C12 176.3(2) . . . . ? C10 C11 C12 C13 0.1(4) . . . . ? C9 N5 C13 C12 0.3(4) . . . . ? C11 C12 C13 N5 0.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.151 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.037 data_NF-4-Picoline(1:1) _database_code_depnum_ccdc_archive 'CCDC 847328' #TrackingRef '7490_web_deposit_cif_file_0_VenuR.Vangala_1317865493.NF-solvates-salt CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1:1 nitrofurantoin and 4-picoline' ; _chemical_name_common '1:1 nitrofurantoin and 4-picoline' _chemical_melting_point ? _chemical_formula_moiety 'C8 H6 N4 O5, C6 H7 N' _chemical_formula_sum 'C14 H13 N5 O5' _chemical_formula_weight 331.29 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 2 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 14.840(3) _cell_length_b 8.0152(16) _cell_length_c 12.951(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.12(3) _cell_angle_gamma 90.00 _cell_volume 1540.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2770 _cell_measurement_theta_min 2.5412 _cell_measurement_theta_max 30.8362 _exptl_crystal_description Platelet _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9759 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn CCD area deterctor' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8809 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 24.50 _reflns_number_total 2513 _reflns_number_gt 2060 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0853P)^2^+1.1119P] 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 2513 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1049 _refine_ls_R_factor_gt 0.0847 _refine_ls_wR_factor_ref 0.2019 _refine_ls_wR_factor_gt 0.1879 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_restrained_S_all 1.183 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.23007(17) 0.5478(3) 0.50044(18) 0.0351(7) Uani 1 1 d . . . O4 O 0.00636(18) 0.1985(3) 0.6757(2) 0.0410(7) Uani 1 1 d . . . N3 N 0.0032(2) 0.2556(4) 0.5003(2) 0.0324(8) Uani 1 1 d . . . O5 O -0.1948(2) 0.0590(3) 0.4185(2) 0.0432(7) Uani 1 1 d . . . N2 N 0.0801(2) 0.3503(4) 0.5014(2) 0.0337(8) Uani 1 1 d . . . O3 O 0.3400(2) 0.6691(4) 0.6435(2) 0.0506(8) Uani 1 1 d . . . N4 N -0.1060(2) 0.1019(4) 0.5641(2) 0.0345(8) Uani 1 1 d . . . C8 C -0.0561(3) 0.2208(5) 0.4124(3) 0.0332(9) Uani 1 1 d . . . H8A H -0.0246 0.1572 0.3585 0.040 Uiso 1 1 calc R . . H8B H -0.0810 0.3248 0.3820 0.040 Uiso 1 1 calc R . . C6 C -0.0278(3) 0.1871(4) 0.5907(3) 0.0311(9) Uani 1 1 d . . . C1 C 0.1870(2) 0.5074(4) 0.4088(3) 0.0318(9) Uani 1 1 d . . . C7 C -0.1283(3) 0.1179(5) 0.4616(3) 0.0339(9) Uani 1 1 d . . . C5 C 0.1062(3) 0.4052(4) 0.4134(3) 0.0334(9) Uani 1 1 d . . . H5A H 0.0730 0.3791 0.3521 0.040 Uiso 1 1 calc R . . C4 C 0.3012(3) 0.6424(5) 0.4717(3) 0.0355(9) Uani 1 1 d . . . N1 N 0.3572(2) 0.7040(4) 0.5536(3) 0.0441(9) Uani 1 1 d . . . O2 O 0.4207(2) 0.7944(4) 0.5269(2) 0.0547(9) Uani 1 1 d . . . C2 C 0.2288(3) 0.5761(4) 0.3276(3) 0.0334(9) Uani 1 1 d . . . H2B H 0.2114 0.5665 0.2568 0.040 Uiso 1 1 calc R . . C3 C 0.3043(3) 0.6660(5) 0.3689(3) 0.0373(10) Uani 1 1 d . . . H3A H 0.3473 0.7288 0.3320 0.045 Uiso 1 1 calc R . . N5 N 0.2242(2) 0.4215(4) 0.8223(2) 0.0363(8) Uani 1 1 d . . . C12 C 0.2881(3) 0.2689(5) 0.6828(3) 0.0388(10) Uani 1 1 d . . . H12A H 0.2813 0.2259 0.6148 0.047 Uiso 1 1 calc R . . C10 C 0.3733(3) 0.3102(5) 0.8373(3) 0.0431(10) Uani 1 1 d . . . H10A H 0.4265 0.2959 0.8784 0.052 Uiso 1 1 calc R . . C13 C 0.2189(3) 0.3568(5) 0.7263(3) 0.0376(10) Uani 1 1 d . . . H13A H 0.1649 0.3726 0.6869 0.045 Uiso 1 1 calc R . . C9 C 0.3010(3) 0.3975(5) 0.8755(3) 0.0393(10) Uani 1 1 d . . . H9A H 0.3062 0.4428 0.9432 0.047 Uiso 1 1 calc R . . C11 C 0.3676(3) 0.2432(5) 0.7381(3) 0.0419(10) Uani 1 1 d . . . C14 C 0.4446(3) 0.1447(7) 0.6943(4) 0.0673(15) Uani 1 1 d . . . H14A H 0.4284 0.1074 0.6243 0.101 Uiso 1 1 calc R . . H14B H 0.4569 0.0474 0.7382 0.101 Uiso 1 1 calc R . . H14C H 0.4984 0.2152 0.6920 0.101 Uiso 1 1 calc R . . H4 H -0.146(3) 0.036(6) 0.607(4) 0.068(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0347(15) 0.0453(15) 0.0253(14) -0.0053(12) -0.0020(12) -0.0014(12) O4 0.0375(16) 0.0583(17) 0.0270(14) 0.0018(13) -0.0033(13) -0.0054(14) N3 0.0348(18) 0.0385(17) 0.0238(16) -0.0001(13) -0.0033(14) -0.0054(15) O5 0.0475(18) 0.0541(17) 0.0277(14) 0.0024(13) -0.0060(13) -0.0128(14) N2 0.0361(19) 0.0384(17) 0.0266(17) -0.0007(14) -0.0007(14) -0.0003(15) O3 0.059(2) 0.0649(19) 0.0276(16) 0.0039(14) -0.0048(14) -0.0116(15) N4 0.0361(19) 0.0415(18) 0.0258(17) 0.0002(15) -0.0003(15) -0.0010(15) C8 0.035(2) 0.040(2) 0.0253(19) -0.0014(17) -0.0030(17) 0.0024(17) C6 0.030(2) 0.0392(19) 0.024(2) -0.0044(16) 0.0009(17) 0.0038(17) C1 0.032(2) 0.037(2) 0.0268(19) -0.0021(16) 0.0003(17) 0.0064(17) C7 0.037(2) 0.037(2) 0.0268(19) -0.0041(17) -0.0067(18) 0.0019(18) C5 0.037(2) 0.0344(19) 0.029(2) -0.0031(16) -0.0048(17) 0.0012(17) C4 0.032(2) 0.041(2) 0.034(2) -0.0028(18) 0.0012(18) -0.0079(18) N1 0.043(2) 0.056(2) 0.0333(19) 0.0011(17) -0.0027(17) -0.0061(18) O2 0.0414(18) 0.079(2) 0.0434(17) 0.0049(16) -0.0032(15) -0.0186(16) C2 0.040(2) 0.037(2) 0.0232(18) -0.0015(16) 0.0018(17) 0.0025(17) C3 0.037(2) 0.042(2) 0.033(2) 0.0031(18) 0.0058(18) -0.0024(18) N5 0.039(2) 0.0445(18) 0.0247(16) 0.0049(14) -0.0020(15) 0.0029(15) C12 0.046(3) 0.040(2) 0.030(2) -0.0073(18) 0.000(2) -0.0038(19) C10 0.036(2) 0.047(2) 0.045(2) 0.000(2) -0.011(2) 0.001(2) C13 0.043(2) 0.040(2) 0.030(2) 0.0039(18) -0.0037(18) -0.0073(19) C9 0.044(3) 0.050(2) 0.0237(19) -0.0013(18) -0.0055(18) 0.000(2) C11 0.043(2) 0.043(2) 0.040(2) -0.0004(19) 0.009(2) -0.003(2) C14 0.053(3) 0.077(3) 0.073(4) -0.012(3) 0.013(3) 0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.358(4) . ? O1 C1 1.376(4) . ? O4 C6 1.207(4) . ? N3 N2 1.371(4) . ? N3 C6 1.380(5) . ? N3 C8 1.451(4) . ? O5 C7 1.220(5) . ? N2 C5 1.289(5) . ? O3 N1 1.229(4) . ? N4 C7 1.367(5) . ? N4 C6 1.384(5) . ? N4 H4 0.98(5) . ? C8 C7 1.504(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C1 C2 1.349(5) . ? C1 C5 1.454(5) . ? C5 H5A 0.9500 . ? C4 C3 1.346(5) . ? C4 N1 1.423(5) . ? N1 O2 1.244(4) . ? C2 C3 1.428(5) . ? C2 H2B 0.9500 . ? C3 H3A 0.9500 . ? N5 C9 1.335(5) . ? N5 C13 1.348(5) . ? C12 C13 1.375(6) . ? C12 C11 1.384(6) . ? C12 H12A 0.9500 . ? C10 C9 1.380(6) . ? C10 C11 1.394(6) . ? C10 H10A 0.9500 . ? C13 H13A 0.9500 . ? C9 H9A 0.9500 . ? C11 C14 1.508(6) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 C4 O1 C1 104.2(3) . . ? N2 N3 C6 120.2(3) . . ? N2 N3 C8 127.3(3) . . ? C6 N3 C8 112.4(3) . . ? C5 N2 N3 116.4(3) . . ? C7 N4 C6 112.4(3) . . ? C7 N4 H4 117(3) . . ? C6 N4 H4 130(3) . . ? N3 C8 C7 101.5(3) . . ? N3 C8 H8A 111.5 . . ? C7 C8 H8A 111.5 . . ? N3 C8 H8B 111.5 . . ? C7 C8 H8B 111.5 . . ? H8A C8 H8B 109.3 . . ? O4 C6 N3 127.0(4) . . ? O4 C6 N4 126.9(3) . . ? N3 C6 N4 106.1(3) . . ? C2 C1 O1 111.3(3) . . ? C2 C1 C5 130.9(4) . . ? O1 C1 C5 117.8(3) . . ? O5 C7 N4 125.9(4) . . ? O5 C7 C8 126.6(3) . . ? N4 C7 C8 107.6(3) . . ? N2 C5 C1 119.4(3) . . ? N2 C5 H5A 120.3 . . ? C1 C5 H5A 120.3 . . ? C3 C4 O1 113.1(3) . . ? C3 C4 N1 131.1(4) . . ? O1 C4 N1 115.8(3) . . ? O3 N1 O2 124.6(4) . . ? O3 N1 C4 119.9(3) . . ? O2 N1 C4 115.5(3) . . ? C1 C2 C3 106.4(3) . . ? C1 C2 H2B 126.8 . . ? C3 C2 H2B 126.8 . . ? C4 C3 C2 105.0(3) . . ? C4 C3 H3A 127.5 . . ? C2 C3 H3A 127.5 . . ? C9 N5 C13 117.1(3) . . ? C13 C12 C11 120.0(4) . . ? C13 C12 H12A 120.0 . . ? C11 C12 H12A 120.0 . . ? C9 C10 C11 119.5(4) . . ? C9 C10 H10A 120.3 . . ? C11 C10 H10A 120.3 . . ? N5 C13 C12 123.0(4) . . ? N5 C13 H13A 118.5 . . ? C12 C13 H13A 118.5 . . ? N5 C9 C10 123.4(4) . . ? N5 C9 H9A 118.3 . . ? C10 C9 H9A 118.3 . . ? C12 C11 C10 117.1(4) . . ? C12 C11 C14 121.9(4) . . ? C10 C11 C14 121.0(4) . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 24.50 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.304 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.062 data_NF-2-Pyridone-ACN(1:1:1) _database_code_depnum_ccdc_archive 'CCDC 847329' #TrackingRef '7490_web_deposit_cif_file_0_VenuR.Vangala_1317865493.NF-solvates-salt CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1:1:1 nitrofurantoin, 2-pyridone and acetonitrile' ; _chemical_name_common '1:1:1 cocrystal of nitrofurantoin, 2-pyridone and acetonitrile' _chemical_melting_point ? _chemical_formula_moiety 'C8 H6 N4 O5, C5 H5 N O, C2 H3 N' _chemical_formula_sum 'C15 H14 N6 O6' _chemical_formula_weight 374.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1736(16) _cell_length_b 9.3544(19) _cell_length_c 11.894(2) _cell_angle_alpha 103.46(3) _cell_angle_beta 109.31(3) _cell_angle_gamma 90.14(3) _cell_volume 831.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2264 _cell_measurement_theta_min 1.8725 _cell_measurement_theta_max 30.9415 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9698 _exptl_absorpt_correction_T_max 0.9847 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn CCD area deterctor' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9022 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3033 _reflns_number_gt 2881 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1075P)^2^+0.2980P] 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 3033 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1744 _refine_ls_wR_factor_gt 0.1714 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_restrained_S_all 1.147 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.70528(17) 0.13856(14) 1.20774(12) 0.0232(4) Uani 1 1 d . . . O4 O 0.33049(18) 0.32016(16) 0.85178(13) 0.0261(4) Uani 1 1 d . . . O5 O 0.72813(19) 0.58348(15) 0.76316(13) 0.0267(4) Uani 1 1 d . . . O3 O 0.74072(19) -0.09671(16) 1.40005(13) 0.0301(4) Uani 1 1 d . . . O2 O 0.51303(19) -0.04093(17) 1.26293(14) 0.0318(4) Uani 1 1 d . . . N3 N 0.6294(2) 0.37793(18) 0.94648(15) 0.0225(4) Uani 1 1 d . . . N1 N 0.6694(2) -0.02933(18) 1.32034(15) 0.0240(4) Uani 1 1 d . . . N4 N 0.4962(2) 0.45529(18) 0.77871(15) 0.0227(4) Uani 1 1 d . . . N2 N 0.6499(2) 0.30116(18) 1.03393(15) 0.0226(4) Uani 1 1 d . . . C8 C 0.7658(3) 0.4611(2) 0.92836(18) 0.0218(4) Uani 1 1 d . . . C2 C 0.9937(3) 0.2079(2) 1.29065(18) 0.0244(4) Uani 1 1 d . . . C6 C 0.4689(3) 0.3765(2) 0.85829(17) 0.0217(4) Uani 1 1 d . . . C5 C 0.8035(3) 0.3093(2) 1.11325(18) 0.0244(4) Uani 1 1 d . . . C3 C 0.9560(3) 0.1045(2) 1.35114(18) 0.0243(4) Uani 1 1 d . . . C4 C 0.7819(3) 0.0679(2) 1.29672(18) 0.0229(4) Uani 1 1 d . . . C1 C 0.8411(3) 0.2251(2) 1.20535(18) 0.0226(4) Uani 1 1 d . . . C7 C 0.6662(3) 0.5093(2) 0.81397(18) 0.0224(4) Uani 1 1 d . . . H8B H 0.812(3) 0.547(2) 0.996(2) 0.021(5) Uiso 1 1 d . . . H4 H 0.402(4) 0.467(3) 0.708(3) 0.041(7) Uiso 1 1 d . . . H3A H 1.034(3) 0.068(3) 1.417(2) 0.028(6) Uiso 1 1 d . . . H5A H 0.908(3) 0.368(2) 1.1174(19) 0.019(5) Uiso 1 1 d . . . H8A H 0.852(3) 0.400(3) 0.912(2) 0.029(6) Uiso 1 1 d . . . H2A H 1.107(4) 0.259(3) 1.310(2) 0.039(7) Uiso 1 1 d . . . C10 C 0.3963(3) 0.6696(2) 0.52795(19) 0.0253(5) Uani 1 1 d . . . H10A H 0.497(3) 0.650(2) 0.5864(19) 0.014(5) Uiso 1 1 d . . . H13A H -0.028(3) 0.721(2) 0.294(2) 0.025(6) Uiso 1 1 d . . . H12A H 0.232(3) 0.855(3) 0.318(2) 0.037(7) Uiso 1 1 d . . . C9 C 0.2379(3) 0.5922(2) 0.51610(18) 0.0223(4) Uani 1 1 d . . . C11 C 0.3947(3) 0.7630(2) 0.45430(19) 0.0272(5) Uani 1 1 d . . . O6 O 0.22636(18) 0.50390(16) 0.58084(13) 0.0281(4) Uani 1 1 d . . . C12 C 0.2397(3) 0.7853(2) 0.36603(19) 0.0273(5) Uani 1 1 d . . . N5 N 0.0909(2) 0.61837(18) 0.42945(15) 0.0230(4) Uani 1 1 d . . . H11A H 0.496(3) 0.812(3) 0.465(2) 0.024(6) Uiso 1 1 d . . . C13 C 0.0884(3) 0.7110(2) 0.35563(18) 0.0246(4) Uani 1 1 d . . . H5 H -0.002(4) 0.575(3) 0.424(2) 0.034(7) Uiso 1 1 d . . . C14 C 0.2920(3) 0.0991(3) 1.0500(2) 0.0318(5) Uani 1 1 d . . . N6 N -0.0094(3) 0.1568(2) 0.91364(18) 0.0352(5) Uani 1 1 d . . . H14A H 0.300(4) -0.004(3) 1.039(2) 0.044(7) Uiso 1 1 d . . . H14B H 0.304(4) 0.146(3) 1.130(3) 0.058(9) Uiso 1 1 d . . . H14C H 0.384(5) 0.137(4) 1.024(3) 0.073(11) Uiso 1 1 d . . . C15 C 0.1233(3) 0.1306(2) 0.97383(18) 0.0261(5) 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 O1 0.0205(7) 0.0253(7) 0.0248(7) 0.0124(6) 0.0047(6) -0.0044(5) O4 0.0196(7) 0.0303(8) 0.0290(8) 0.0095(6) 0.0075(6) -0.0062(6) O5 0.0285(8) 0.0257(7) 0.0306(8) 0.0124(6) 0.0124(6) -0.0037(6) O3 0.0302(8) 0.0333(8) 0.0286(8) 0.0181(6) 0.0054(6) -0.0036(6) O2 0.0205(8) 0.0371(8) 0.0388(9) 0.0177(7) 0.0057(6) -0.0066(6) N3 0.0216(9) 0.0245(8) 0.0248(8) 0.0139(6) 0.0069(7) -0.0035(7) N1 0.0244(9) 0.0252(8) 0.0236(8) 0.0105(7) 0.0069(7) -0.0037(7) N4 0.0210(9) 0.0248(8) 0.0240(8) 0.0115(7) 0.0060(7) -0.0023(6) N2 0.0262(9) 0.0213(8) 0.0241(8) 0.0101(6) 0.0103(7) -0.0016(6) C8 0.0186(10) 0.0225(9) 0.0265(10) 0.0101(8) 0.0078(8) -0.0028(8) C2 0.0223(10) 0.0252(10) 0.0285(10) 0.0108(8) 0.0095(8) -0.0025(8) C6 0.0223(10) 0.0194(9) 0.0250(9) 0.0076(7) 0.0086(8) -0.0017(7) C5 0.0241(10) 0.0249(10) 0.0256(10) 0.0096(8) 0.0081(8) -0.0026(8) C3 0.0236(11) 0.0258(10) 0.0256(10) 0.0106(8) 0.0081(8) -0.0003(8) C4 0.0249(10) 0.0225(9) 0.0238(9) 0.0108(7) 0.0083(8) -0.0015(8) C1 0.0205(10) 0.0234(9) 0.0259(9) 0.0081(7) 0.0093(8) -0.0032(7) C7 0.0228(10) 0.0206(9) 0.0262(10) 0.0093(7) 0.0091(8) -0.0014(7) C10 0.0196(10) 0.0296(10) 0.0273(10) 0.0113(8) 0.0060(8) -0.0011(8) C9 0.0215(10) 0.0242(9) 0.0233(9) 0.0098(7) 0.0077(8) -0.0017(8) C11 0.0251(11) 0.0271(10) 0.0319(11) 0.0084(8) 0.0123(9) -0.0056(8) O6 0.0218(7) 0.0344(8) 0.0319(8) 0.0187(6) 0.0068(6) -0.0021(6) C12 0.0309(11) 0.0237(10) 0.0301(10) 0.0109(8) 0.0111(9) -0.0002(8) N5 0.0194(9) 0.0254(8) 0.0260(9) 0.0105(7) 0.0072(7) -0.0041(7) C13 0.0271(11) 0.0241(10) 0.0248(10) 0.0116(8) 0.0077(8) 0.0023(8) C14 0.0269(12) 0.0276(11) 0.0380(12) 0.0092(9) 0.0066(9) -0.0019(9) N6 0.0332(11) 0.0370(10) 0.0362(10) 0.0149(8) 0.0090(9) 0.0021(8) C15 0.0298(12) 0.0220(9) 0.0294(10) 0.0095(8) 0.0118(9) -0.0033(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 O1 C4 1.356(2) . ? O1 C1 1.384(2) . ? O4 C6 1.218(2) . ? O5 C7 1.224(2) . ? O3 N1 1.245(2) . ? O2 N1 1.225(2) . ? N3 N2 1.363(2) . ? N3 C6 1.380(3) . ? N3 C8 1.458(2) . ? N1 C4 1.427(3) . ? N4 C7 1.369(3) . ? N4 C6 1.397(2) . ? N2 C5 1.286(3) . ? C8 C7 1.507(3) . ? C2 C1 1.360(3) . ? C2 C3 1.420(3) . ? C5 C1 1.447(3) . ? C3 C4 1.359(3) . ? C10 C11 1.371(3) . ? C10 C9 1.431(3) . ? C9 O6 1.276(2) . ? C9 N5 1.366(3) . ? C11 C12 1.405(3) . ? C12 C13 1.372(3) . ? N5 C13 1.366(2) . ? C14 C15 1.453(3) . ? N6 C15 1.148(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 C4 O1 C1 104.07(15) . . ? N2 N3 C6 120.87(16) . . ? N2 N3 C8 126.81(17) . . ? C6 N3 C8 112.24(16) . . ? O2 N1 O3 124.77(17) . . ? O2 N1 C4 119.20(17) . . ? O3 N1 C4 116.03(17) . . ? C7 N4 C6 112.29(17) . . ? C5 N2 N3 116.90(17) . . ? N3 C8 C7 101.80(16) . . ? C1 C2 C3 107.05(17) . . ? O4 C6 N3 127.18(18) . . ? O4 C6 N4 126.65(18) . . ? N3 C6 N4 106.16(16) . . ? N2 C5 C1 121.19(18) . . ? C4 C3 C2 104.55(17) . . ? O1 C4 C3 113.48(17) . . ? O1 C4 N1 116.17(18) . . ? C3 C4 N1 130.33(18) . . ? C2 C1 O1 110.86(17) . . ? C2 C1 C5 131.15(18) . . ? O1 C1 C5 117.90(17) . . ? O5 C7 N4 126.97(18) . . ? O5 C7 C8 125.52(18) . . ? N4 C7 C8 107.50(16) . . ? C11 C10 C9 120.10(19) . . ? O6 C9 N5 119.30(18) . . ? O6 C9 C10 124.61(19) . . ? N5 C9 C10 116.09(18) . . ? C10 C11 C12 121.5(2) . . ? C13 C12 C11 118.01(19) . . ? C13 N5 C9 124.14(18) . . ? N5 C13 C12 120.18(19) . . ? N6 C15 C14 179.4(2) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.334 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.085 data_NF-DMAPsalt(1:1) _database_code_depnum_ccdc_archive 'CCDC 847330' #TrackingRef '7490_web_deposit_cif_file_0_VenuR.Vangala_1317865493.NF-solvates-salt CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1:1 salt of nitrofurantoin and 4-dimethylaminopyridine' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 N6 O5' _chemical_formula_weight 360.34 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 2 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 8.616(4) _cell_length_b 26.655(11) _cell_length_c 7.029(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.722(9) _cell_angle_gamma 90.00 _cell_volume 1586.1(12) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2936 _cell_measurement_theta_min 2.8505 _cell_measurement_theta_max 31.0924 _exptl_crystal_description Block _exptl_crystal_colour 'Orange yellow' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9748 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn CCD area deterctor' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16954 _diffrn_reflns_av_R_equivalents 0.0896 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 24.24 _reflns_number_total 2524 _reflns_number_gt 2260 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+3.8985P] 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 2524 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1133 _refine_ls_R_factor_gt 0.0996 _refine_ls_wR_factor_ref 0.1857 _refine_ls_wR_factor_gt 0.1785 _refine_ls_goodness_of_fit_ref 1.247 _refine_ls_restrained_S_all 1.247 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.4329(4) -0.07536(11) -0.6081(4) 0.0288(8) Uani 1 1 d . . . O2 O -0.1982(4) -0.12607(12) -0.4023(5) 0.0351(9) Uani 1 1 d . . . O3 O -0.0354(4) -0.06290(13) -0.4044(5) 0.0376(9) Uani 1 1 d . . . O4 O -0.9275(4) -0.17594(12) -0.6637(5) 0.0336(8) Uani 1 1 d . . . O5 O -1.2938(4) -0.07598(13) -1.0382(5) 0.0383(9) Uani 1 1 d . . . N1 N -0.1678(5) -0.08273(14) -0.4481(5) 0.0291(9) Uani 1 1 d . . . N2 N -0.7495(5) -0.09277(14) -0.7461(6) 0.0291(9) Uani 1 1 d . . . N3 N -0.9047(4) -0.09966(14) -0.8169(6) 0.0280(9) Uani 1 1 d . . . N4 N -1.1463(4) -0.13635(14) -0.8461(6) 0.0290(9) Uani 1 1 d . . . C1 C -0.5256(5) -0.03970(17) -0.7176(7) 0.0283(11) Uani 1 1 d . . . C2 C -0.4380(6) 0.00235(17) -0.7324(7) 0.0312(12) Uani 1 1 d . . . H2B H -0.4742 0.0322 -0.8007 0.037 Uiso 1 1 calc R . . C3 C -0.2843(6) -0.00654(17) -0.6280(7) 0.0294(11) Uani 1 1 d . . . H3A H -0.1969 0.0158 -0.6100 0.035 Uiso 1 1 calc R . . C4 C -0.2884(5) -0.05374(17) -0.5592(7) 0.0285(11) Uani 1 1 d . . . C5 C -0.6871(5) -0.05069(17) -0.7887(7) 0.0281(11) Uani 1 1 d . . . H5A H -0.7508 -0.0270 -0.8687 0.034 Uiso 1 1 calc R . . C6 C -0.9891(6) -0.14149(17) -0.7646(7) 0.0284(11) Uani 1 1 d . . . C7 C -1.1676(6) -0.09272(18) -0.9451(7) 0.0312(11) Uani 1 1 d . . . C8 C -1.0128(5) -0.06425(17) -0.9271(7) 0.0309(11) Uani 1 1 d . . . H8A H -0.9855 -0.0575 -1.0554 0.037 Uiso 1 1 calc R . . H8B H -1.0158 -0.0322 -0.8565 0.037 Uiso 1 1 calc R . . N5 N -0.3489(4) -0.28999(14) -0.2639(5) 0.0296(10) Uani 1 1 d . . . H5 H -0.2773 -0.3129 -0.2774 0.035 Uiso 1 1 d R . . N6 N -0.6904(4) -0.18445(14) -0.2132(6) 0.0297(9) Uani 1 1 d . . . C9 C -0.4938(6) -0.30423(18) -0.2416(7) 0.0300(11) Uani 1 1 d . . . H9 H -0.5166 -0.3391 -0.2394 0.036 Uiso 1 1 calc R . . C10 C -0.6096(5) -0.27090(17) -0.2220(7) 0.0283(11) Uani 1 1 d . . . H10 H -0.7107 -0.2825 -0.2060 0.034 Uiso 1 1 calc R . . C11 C -0.5781(6) -0.21890(17) -0.2257(6) 0.0270(11) Uani 1 1 d . . . C12 C -0.4230(6) -0.20441(18) -0.2436(7) 0.0320(12) Uani 1 1 d . . . H12 H -0.3950 -0.1699 -0.2422 0.038 Uiso 1 1 calc R . . C13 C -0.3147(6) -0.24037(18) -0.2628(7) 0.0305(11) Uani 1 1 d . . . H13 H -0.2114 -0.2303 -0.2758 0.037 Uiso 1 1 calc R . . C14 C -0.6598(6) -0.13103(17) -0.2337(8) 0.0377(13) Uani 1 1 d . . . H14A H -0.5673 -0.1211 -0.1377 0.057 Uiso 1 1 calc R . . H14B H -0.7519 -0.1117 -0.2130 0.057 Uiso 1 1 calc R . . H14C H -0.6397 -0.1245 -0.3641 0.057 Uiso 1 1 calc R . . C15 C -0.8513(5) -0.19909(18) -0.1990(7) 0.0341(12) Uani 1 1 d . . . H15A H -0.9066 -0.2111 -0.3253 0.051 Uiso 1 1 calc R . . H15B H -0.9074 -0.1701 -0.1592 0.051 Uiso 1 1 calc R . . H15C H -0.8477 -0.2259 -0.1029 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0267(18) 0.0269(18) 0.0311(18) -0.0015(14) 0.0005(14) -0.0010(14) O2 0.034(2) 0.031(2) 0.040(2) 0.0038(16) 0.0039(16) -0.0028(15) O3 0.028(2) 0.042(2) 0.040(2) 0.0021(16) -0.0002(16) -0.0047(16) O4 0.038(2) 0.0251(18) 0.038(2) 0.0050(15) 0.0063(16) 0.0021(15) O5 0.032(2) 0.038(2) 0.043(2) -0.0010(17) -0.0003(17) 0.0049(16) N1 0.031(2) 0.030(2) 0.027(2) 0.0015(17) 0.0062(18) -0.0030(19) N2 0.029(2) 0.027(2) 0.031(2) -0.0031(17) 0.0062(18) -0.0007(18) N3 0.023(2) 0.024(2) 0.036(2) 0.0056(17) 0.0002(18) -0.0007(16) N4 0.029(2) 0.024(2) 0.033(2) 0.0010(17) 0.0042(18) -0.0026(17) C1 0.032(3) 0.021(2) 0.032(3) 0.001(2) 0.007(2) 0.003(2) C2 0.035(3) 0.023(3) 0.036(3) 0.002(2) 0.007(2) 0.002(2) C3 0.030(3) 0.024(3) 0.035(3) -0.005(2) 0.008(2) -0.005(2) C4 0.030(3) 0.024(2) 0.030(3) -0.008(2) 0.002(2) -0.004(2) C5 0.027(3) 0.031(3) 0.027(3) -0.001(2) 0.007(2) 0.004(2) C6 0.036(3) 0.025(3) 0.025(3) 0.000(2) 0.008(2) -0.002(2) C7 0.036(3) 0.030(3) 0.030(3) -0.005(2) 0.010(2) 0.006(2) C8 0.037(3) 0.025(3) 0.028(3) 0.001(2) -0.002(2) 0.000(2) N5 0.029(2) 0.030(2) 0.029(2) -0.0005(17) 0.0043(18) 0.0057(18) N6 0.032(2) 0.022(2) 0.035(2) 0.0025(17) 0.0075(19) 0.0025(17) C9 0.033(3) 0.025(3) 0.031(3) 0.003(2) 0.004(2) 0.000(2) C10 0.025(3) 0.033(3) 0.026(3) 0.002(2) 0.002(2) -0.002(2) C11 0.034(3) 0.023(2) 0.024(3) 0.0008(19) 0.007(2) 0.000(2) C12 0.043(3) 0.025(3) 0.027(3) 0.001(2) 0.004(2) 0.000(2) C13 0.029(3) 0.035(3) 0.029(3) -0.001(2) 0.008(2) -0.002(2) C14 0.038(3) 0.024(3) 0.047(3) 0.001(2) -0.002(3) 0.001(2) C15 0.030(3) 0.032(3) 0.038(3) 0.001(2) 0.002(2) 0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.356(5) . ? O1 C1 1.380(5) . ? O2 N1 1.241(5) . ? O3 N1 1.243(5) . ? O4 C6 1.220(5) . ? O5 C7 1.243(6) . ? N1 C4 1.409(6) . ? N2 C5 1.302(6) . ? N2 N3 1.350(5) . ? N3 C6 1.416(6) . ? N3 C8 1.445(6) . ? N4 C7 1.350(6) . ? N4 C6 1.376(6) . ? C1 C2 1.366(6) . ? C1 C5 1.419(6) . ? C2 C3 1.410(7) . ? C2 H2B 0.9500 . ? C3 C4 1.351(6) . ? C3 H3A 0.9500 . ? C5 H5A 0.9500 . ? C7 C8 1.519(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? N5 C9 1.342(6) . ? N5 C13 1.355(6) . ? N5 H5 0.8857 . ? N6 C11 1.348(6) . ? N6 C14 1.460(6) . ? N6 C15 1.461(6) . ? C9 C10 1.362(6) . ? C9 H9 0.9500 . ? C10 C11 1.414(6) . ? C10 H10 0.9500 . ? C11 C12 1.419(7) . ? C12 C13 1.362(7) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 C4 O1 C1 104.9(3) . . ? O2 N1 O3 124.1(4) . . ? O2 N1 C4 119.0(4) . . ? O3 N1 C4 116.9(4) . . ? C5 N2 N3 117.1(4) . . ? N2 N3 C6 122.2(4) . . ? N2 N3 C8 127.2(4) . . ? C6 N3 C8 110.0(4) . . ? C7 N4 C6 109.2(4) . . ? C2 C1 O1 109.7(4) . . ? C2 C1 C5 131.4(4) . . ? O1 C1 C5 118.8(4) . . ? C1 C2 C3 107.5(4) . . ? C1 C2 H2B 126.2 . . ? C3 C2 H2B 126.2 . . ? C4 C3 C2 105.0(4) . . ? C4 C3 H3A 127.5 . . ? C2 C3 H3A 127.5 . . ? C3 C4 O1 112.9(4) . . ? C3 C4 N1 130.0(4) . . ? O1 C4 N1 117.0(4) . . ? N2 C5 C1 121.1(4) . . ? N2 C5 H5A 119.5 . . ? C1 C5 H5A 119.5 . . ? O4 C6 N4 127.2(4) . . ? O4 C6 N3 123.7(4) . . ? N4 C6 N3 109.1(4) . . ? O5 C7 N4 127.0(5) . . ? O5 C7 C8 122.2(4) . . ? N4 C7 C8 110.8(4) . . ? N3 C8 C7 100.7(4) . . ? N3 C8 H8A 111.6 . . ? C7 C8 H8A 111.6 . . ? N3 C8 H8B 111.6 . . ? C7 C8 H8B 111.6 . . ? H8A C8 H8B 109.4 . . ? C9 N5 C13 118.8(4) . . ? C9 N5 H5 119.9 . . ? C13 N5 H5 121.3 . . ? C11 N6 C14 120.9(4) . . ? C11 N6 C15 121.6(4) . . ? C14 N6 C15 117.3(4) . . ? N5 C9 C10 122.9(4) . . ? N5 C9 H9 118.6 . . ? C10 C9 H9 118.6 . . ? C9 C10 C11 119.4(4) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? N6 C11 C10 121.6(4) . . ? N6 C11 C12 121.3(4) . . ? C10 C11 C12 117.1(4) . . ? C13 C12 C11 119.4(4) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? N5 C13 C12 122.4(4) . . ? N5 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? N6 C14 H14A 109.5 . . ? N6 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N6 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N6 C15 H15A 109.5 . . ? N6 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N6 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? 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 C5 N2 N3 C6 -173.5(4) . . . . ? C5 N2 N3 C8 -3.6(6) . . . . ? C4 O1 C1 C2 -0.3(5) . . . . ? C4 O1 C1 C5 -178.7(4) . . . . ? O1 C1 C2 C3 -0.3(5) . . . . ? C5 C1 C2 C3 177.8(5) . . . . ? C1 C2 C3 C4 0.9(5) . . . . ? C2 C3 C4 O1 -1.2(5) . . . . ? C2 C3 C4 N1 178.7(5) . . . . ? C1 O1 C4 C3 1.0(5) . . . . ? C1 O1 C4 N1 -178.9(4) . . . . ? O2 N1 C4 C3 -179.2(5) . . . . ? O3 N1 C4 C3 -0.2(7) . . . . ? O2 N1 C4 O1 0.6(6) . . . . ? O3 N1 C4 O1 179.7(4) . . . . ? N3 N2 C5 C1 178.7(4) . . . . ? C2 C1 C5 N2 -175.4(5) . . . . ? O1 C1 C5 N2 2.6(7) . . . . ? C7 N4 C6 O4 179.1(5) . . . . ? C7 N4 C6 N3 -1.2(5) . . . . ? N2 N3 C6 O4 -5.1(7) . . . . ? C8 N3 C6 O4 -176.6(4) . . . . ? N2 N3 C6 N4 175.2(4) . . . . ? C8 N3 C6 N4 3.7(5) . . . . ? C6 N4 C7 O5 179.3(4) . . . . ? C6 N4 C7 C8 -1.6(5) . . . . ? N2 N3 C8 C7 -175.2(4) . . . . ? C6 N3 C8 C7 -4.2(5) . . . . ? O5 C7 C8 N3 -177.3(4) . . . . ? N4 C7 C8 N3 3.6(5) . . . . ? C13 N5 C9 C10 1.5(7) . . . . ? N5 C9 C10 C11 0.2(7) . . . . ? C14 N6 C11 C10 -174.7(4) . . . . ? C15 N6 C11 C10 -1.2(7) . . . . ? C14 N6 C11 C12 5.1(7) . . . . ? C15 N6 C11 C12 178.6(4) . . . . ? C9 C10 C11 N6 177.8(4) . . . . ? C9 C10 C11 C12 -2.0(7) . . . . ? N6 C11 C12 C13 -177.7(4) . . . . ? C10 C11 C12 C13 2.2(7) . . . . ? C9 N5 C13 C12 -1.3(7) . . . . ? C11 C12 C13 N5 -0.6(7) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 24.24 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.299 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.072 #====END data_NF-4-Aminobenzamide-ACN(1:1:1) _database_code_depnum_ccdc_archive 'CCDC 861182' #TrackingRef '8904_web_deposit_cif_file_0_VenuR.Vangala_1325759692. #NF-solvates-salt CIF-part2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1:1:1 cocrystal of nitrofurantoin, 2-pyridone and acetonitrile' ; _chemical_name_common ; '1:1:1 cocrystal of nitrofurantoin, 2-pyridone and acetonitrile' ; _chemical_melting_point ? _chemical_formula_moiety 'C8 H6 N4 O5, C7 H8 N2 O, C2 H3 N' _chemical_formula_sum 'C17 H17 N7 O6' _chemical_formula_weight 415.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 7.2712(15) _cell_length_b 18.918(4) _cell_length_c 15.451(4) _cell_angle_alpha 90.00 _cell_angle_beta 117.41(2) _cell_angle_gamma 90.00 _cell_volume 1886.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5611 _cell_measurement_theta_min 1.8339 _cell_measurement_theta_max 31.1906 _exptl_crystal_description Block _exptl_crystal_colour 'Orange Red' _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.44 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9515 _exptl_absorpt_correction_T_max 0.9515 _exptl_absorpt_process_details '(SADABS, Rigaku 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn CCD area deterctor' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10631 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3303 _reflns_number_gt 3154 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+0.9166P] 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 3303 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _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 N7 N 0.0645(2) 0.84275(9) 0.46603(12) 0.0411(4) Uani 1 1 d . . . C16 C -0.0488(3) 0.88246(9) 0.47065(12) 0.0315(4) Uani 1 1 d . . . C17 C -0.1933(3) 0.93220(10) 0.47856(13) 0.0347(4) Uani 1 1 d . . . H17A H -0.1366 0.9492 0.5459 0.052 Uiso 1 1 calc R . . H17B H -0.3261 0.9085 0.4602 0.052 Uiso 1 1 calc R . . H17C H -0.2146 0.9723 0.4349 0.052 Uiso 1 1 calc R . . N2 N 0.27796(18) 0.42214(6) 0.48620(9) 0.0189(3) Uani 1 1 d . . . N3 N 0.42299(18) 0.45262(6) 0.56917(8) 0.0194(3) Uani 1 1 d . . . N4 N 0.56072(19) 0.53740(7) 0.67897(9) 0.0218(3) Uani 1 1 d . . . H4A H 0.5711 0.5815 0.7059 0.026 Uiso 1 1 d R . . C1 C 0.1410(2) 0.31725(8) 0.39580(11) 0.0208(3) Uani 1 1 d . . . C2 C 0.1114(2) 0.24627(8) 0.37896(12) 0.0252(3) Uani 1 1 d . . . H2A H 0.1918 0.2095 0.4214 0.030 Uiso 1 1 calc R . . C3 C -0.0611(2) 0.23794(8) 0.28658(12) 0.0275(4) Uani 1 1 d . . . H3A H -0.1209 0.1949 0.2541 0.033 Uiso 1 1 calc R . . C4 C -0.1229(2) 0.30427(8) 0.25436(11) 0.0245(3) Uani 1 1 d . . . C5 C 0.2921(2) 0.35482(8) 0.47887(11) 0.0204(3) Uani 1 1 d . . . H5C H 0.4035 0.3297 0.5289 0.024 Uiso 1 1 calc R . . C6 C 0.4041(2) 0.52299(8) 0.58661(10) 0.0189(3) Uani 1 1 d . . . C7 C 0.6820(2) 0.47964(8) 0.72230(11) 0.0215(3) Uani 1 1 d . . . C8 C 0.5961(2) 0.41906(8) 0.65054(10) 0.0205(3) Uani 1 1 d . . . H8B H 0.6998 0.4012 0.6312 0.025 Uiso 1 1 calc R . . H8A H 0.5492 0.3797 0.6777 0.025 Uiso 1 1 calc R . . O1 O -0.00481(15) 0.35449(5) 0.31866(7) 0.0223(2) Uani 1 1 d . . . O2 O -0.30821(18) 0.39442(7) 0.15423(9) 0.0363(3) Uani 1 1 d . . . O3 O -0.39654(19) 0.28543(7) 0.10618(9) 0.0401(3) Uani 1 1 d . . . O4 O 0.27639(16) 0.56433(5) 0.53105(7) 0.0227(2) Uani 1 1 d . . . O5 O 0.82904(17) 0.47672(6) 0.80260(8) 0.0294(3) Uani 1 1 d . . . N1 N -0.2864(2) 0.33015(8) 0.16605(10) 0.0298(3) Uani 1 1 d . . . H6B H 1.0119 0.9870 0.8878 0.036 Uiso 1 1 d R . . C9 C 0.8128(2) 0.92400(8) 0.79220(11) 0.0208(3) Uani 1 1 d . . . C10 C 0.8650(2) 0.86269(8) 0.85013(11) 0.0213(3) Uani 1 1 d . . . H10A H 0.9741 0.8643 0.9150 0.026 Uiso 1 1 calc R . . C11 C 0.7595(2) 0.80020(8) 0.81387(11) 0.0212(3) Uani 1 1 d . . . H11A H 0.7967 0.7595 0.8544 0.025 Uiso 1 1 calc R . . C12 C 0.5989(2) 0.79567(8) 0.71853(11) 0.0208(3) Uani 1 1 d . . . C13 C 0.5477(2) 0.85637(8) 0.66043(11) 0.0221(3) Uani 1 1 d . . . H13A H 0.4394 0.8543 0.5954 0.027 Uiso 1 1 calc R . . C14 C 0.6519(2) 0.91922(8) 0.69600(11) 0.0222(3) Uani 1 1 d . . . H14A H 0.6147 0.9597 0.6551 0.027 Uiso 1 1 calc R . . C15 C 0.5053(2) 0.72498(8) 0.68331(11) 0.0219(3) Uani 1 1 d . . . O6 O 0.57022(18) 0.67263(6) 0.73824(8) 0.0292(3) Uani 1 1 d . . . N5 N 0.3546(2) 0.71836(7) 0.59170(9) 0.0247(3) Uani 1 1 d . . . H5B H 0.3054 0.6751 0.5716 0.030 Uiso 1 1 d R . . H5A H 0.2924 0.7559 0.5526 0.030 Uiso 1 1 d R . . N6 N 0.9118(2) 0.98624(7) 0.82827(10) 0.0265(3) Uani 1 1 d . . . H6A H 0.8821 1.0226 0.7896 0.032 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N7 0.0343(8) 0.0376(9) 0.0416(9) -0.0015(7) 0.0089(7) -0.0020(7) C16 0.0266(8) 0.0329(9) 0.0256(9) 0.0047(7) 0.0038(7) -0.0068(8) C17 0.0272(8) 0.0399(10) 0.0312(9) 0.0041(8) 0.0085(7) -0.0024(7) N2 0.0201(6) 0.0182(6) 0.0172(6) -0.0014(5) 0.0078(5) -0.0009(5) N3 0.0202(6) 0.0168(6) 0.0155(6) 0.0006(5) 0.0033(5) 0.0012(5) N4 0.0231(6) 0.0196(6) 0.0187(6) -0.0016(5) 0.0061(5) -0.0012(5) C1 0.0219(7) 0.0193(7) 0.0234(8) 0.0005(6) 0.0122(6) 0.0019(6) C2 0.0289(8) 0.0193(7) 0.0336(8) -0.0015(6) 0.0196(7) -0.0001(6) C3 0.0297(8) 0.0221(8) 0.0369(9) -0.0113(7) 0.0207(7) -0.0067(6) C4 0.0226(7) 0.0266(8) 0.0249(8) -0.0102(6) 0.0115(6) -0.0056(6) C5 0.0226(7) 0.0188(7) 0.0208(7) 0.0021(6) 0.0109(6) 0.0021(6) C6 0.0203(7) 0.0185(7) 0.0181(7) 0.0007(6) 0.0091(6) -0.0016(6) C7 0.0204(7) 0.0254(8) 0.0190(7) 0.0031(6) 0.0094(6) -0.0005(6) C8 0.0192(7) 0.0204(7) 0.0194(7) 0.0045(6) 0.0067(6) 0.0031(6) O1 0.0229(5) 0.0188(5) 0.0217(6) -0.0039(4) 0.0072(5) -0.0015(4) O2 0.0321(6) 0.0350(7) 0.0322(7) -0.0016(5) 0.0067(5) 0.0024(5) O3 0.0328(6) 0.0497(8) 0.0316(7) -0.0196(6) 0.0096(5) -0.0151(6) O4 0.0253(5) 0.0167(5) 0.0217(5) 0.0018(4) 0.0068(5) 0.0025(4) O5 0.0249(6) 0.0359(7) 0.0194(6) 0.0017(5) 0.0035(5) 0.0013(5) N1 0.0248(7) 0.0365(9) 0.0260(7) -0.0102(6) 0.0100(6) -0.0048(6) C9 0.0207(7) 0.0209(7) 0.0237(8) -0.0051(6) 0.0125(6) -0.0015(6) C10 0.0192(7) 0.0233(8) 0.0198(7) -0.0030(6) 0.0075(6) 0.0005(6) C11 0.0226(7) 0.0207(7) 0.0220(7) -0.0009(6) 0.0117(6) 0.0014(6) C12 0.0213(7) 0.0199(7) 0.0227(7) -0.0043(6) 0.0113(6) -0.0002(6) C13 0.0214(7) 0.0223(8) 0.0209(7) -0.0034(6) 0.0083(6) 0.0001(6) C14 0.0234(7) 0.0197(7) 0.0229(8) 0.0005(6) 0.0100(6) 0.0009(6) C15 0.0226(7) 0.0216(8) 0.0242(8) -0.0041(6) 0.0131(6) -0.0004(6) O6 0.0381(6) 0.0186(6) 0.0264(6) -0.0020(5) 0.0110(5) -0.0024(5) N5 0.0265(7) 0.0183(6) 0.0243(7) -0.0049(5) 0.0075(5) -0.0024(5) N6 0.0285(7) 0.0212(7) 0.0265(7) -0.0036(5) 0.0099(6) -0.0049(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 N7 C16 1.141(2) . ? C16 C17 1.457(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? N2 C5 1.2869(19) . ? N2 N3 1.3577(17) . ? N3 C6 1.3775(19) . ? N3 C8 1.4531(18) . ? N4 C7 1.3697(19) . ? N4 C6 1.3825(19) . ? N4 H4A 0.9190 . ? C1 C2 1.366(2) . ? C1 O1 1.3701(18) . ? C1 C5 1.436(2) . ? C2 C3 1.410(2) . ? C2 H2A 0.9500 . ? C3 C4 1.348(2) . ? C3 H3A 0.9500 . ? C4 O1 1.3569(18) . ? C4 N1 1.422(2) . ? C5 H5C 0.9500 . ? C6 O4 1.2154(18) . ? C7 O5 1.2101(19) . ? C7 C8 1.515(2) . ? C8 H8B 0.9900 . ? C8 H8A 0.9900 . ? O2 N1 1.2289(19) . ? O3 N1 1.2373(18) . ? C9 N6 1.359(2) . ? C9 C10 1.406(2) . ? C9 C14 1.409(2) . ? C10 C11 1.380(2) . ? C10 H10A 0.9500 . ? C11 C12 1.399(2) . ? C11 H11A 0.9500 . ? C12 C13 1.398(2) . ? C12 C15 1.486(2) . ? C13 C14 1.381(2) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 O6 1.2469(19) . ? C15 N5 1.339(2) . ? N5 H5B 0.8897 . ? N5 H5A 0.9077 . ? N6 H6B 0.8718 . ? N6 H6A 0.8711 . ? 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 N7 C16 C17 178.58(19) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C5 N2 N3 116.40(12) . . ? N2 N3 C6 119.42(12) . . ? N2 N3 C8 128.20(12) . . ? C6 N3 C8 112.19(12) . . ? C7 N4 C6 112.72(12) . . ? C7 N4 H4A 127.0 . . ? C6 N4 H4A 120.2 . . ? C2 C1 O1 110.42(13) . . ? C2 C1 C5 130.20(14) . . ? O1 C1 C5 119.37(13) . . ? C1 C2 C3 106.94(14) . . ? C1 C2 H2A 126.5 . . ? C3 C2 H2A 126.5 . . ? C4 C3 C2 105.05(14) . . ? C4 C3 H3A 127.5 . . ? C2 C3 H3A 127.5 . . ? C3 C4 O1 112.97(14) . . ? C3 C4 N1 131.61(14) . . ? O1 C4 N1 115.42(14) . . ? N2 C5 C1 120.62(14) . . ? N2 C5 H5C 119.7 . . ? C1 C5 H5C 119.7 . . ? O4 C6 N3 126.60(13) . . ? O4 C6 N4 126.91(14) . . ? N3 C6 N4 106.48(12) . . ? O5 C7 N4 127.14(14) . . ? O5 C7 C8 126.00(14) . . ? N4 C7 C8 106.86(12) . . ? N3 C8 C7 101.75(12) . . ? N3 C8 H8B 111.4 . . ? C7 C8 H8B 111.4 . . ? N3 C8 H8A 111.4 . . ? C7 C8 H8A 111.4 . . ? H8B C8 H8A 109.3 . . ? C4 O1 C1 104.61(12) . . ? O2 N1 O3 124.78(15) . . ? O2 N1 C4 118.50(13) . . ? O3 N1 C4 116.72(14) . . ? N6 C9 C10 121.12(14) . . ? N6 C9 C14 120.94(14) . . ? C10 C9 C14 117.93(13) . . ? C11 C10 C9 120.75(14) . . ? C11 C10 H10A 119.6 . . ? C9 C10 H10A 119.6 . . ? C10 C11 C12 121.25(14) . . ? C10 C11 H11A 119.4 . . ? C12 C11 H11A 119.4 . . ? C13 C12 C11 118.17(14) . . ? C13 C12 C15 124.22(14) . . ? C11 C12 C15 117.43(13) . . ? C14 C13 C12 121.09(14) . . ? C14 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C13 C14 C9 120.81(14) . . ? C13 C14 H14A 119.6 . . ? C9 C14 H14A 119.6 . . ? O6 C15 N5 120.97(14) . . ? O6 C15 C12 119.97(14) . . ? N5 C15 C12 119.04(13) . . ? C15 N5 H5B 117.2 . . ? C15 N5 H5A 123.1 . . ? H5B N5 H5A 119.4 . . ? C9 N6 H6B 118.3 . . ? C9 N6 H6A 119.1 . . ? H6B N6 H6A 122.3 . . ? 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 C5 N2 N3 C6 -172.96(13) . . . . ? C5 N2 N3 C8 1.5(2) . . . . ? O1 C1 C2 C3 0.14(16) . . . . ? C5 C1 C2 C3 178.89(15) . . . . ? C1 C2 C3 C4 0.10(17) . . . . ? C2 C3 C4 O1 -0.31(17) . . . . ? C2 C3 C4 N1 179.22(15) . . . . ? N3 N2 C5 C1 177.35(12) . . . . ? C2 C1 C5 N2 -170.93(15) . . . . ? O1 C1 C5 N2 7.7(2) . . . . ? N2 N3 C6 O4 -6.2(2) . . . . ? C8 N3 C6 O4 178.57(14) . . . . ? N2 N3 C6 N4 174.71(11) . . . . ? C8 N3 C6 N4 -0.56(16) . . . . ? C7 N4 C6 O4 -178.66(14) . . . . ? C7 N4 C6 N3 0.47(16) . . . . ? C6 N4 C7 O5 -179.79(14) . . . . ? C6 N4 C7 C8 -0.20(16) . . . . ? N2 N3 C8 C7 -174.32(13) . . . . ? C6 N3 C8 C7 0.43(15) . . . . ? O5 C7 C8 N3 179.46(14) . . . . ? N4 C7 C8 N3 -0.14(15) . . . . ? C3 C4 O1 C1 0.39(16) . . . . ? N1 C4 O1 C1 -179.22(12) . . . . ? C2 C1 O1 C4 -0.32(15) . . . . ? C5 C1 O1 C4 -179.22(13) . . . . ? C3 C4 N1 O2 -179.20(16) . . . . ? O1 C4 N1 O2 0.3(2) . . . . ? C3 C4 N1 O3 0.6(2) . . . . ? O1 C4 N1 O3 -179.93(13) . . . . ? N6 C9 C10 C11 178.06(13) . . . . ? C14 C9 C10 C11 -0.8(2) . . . . ? C9 C10 C11 C12 0.4(2) . . . . ? C10 C11 C12 C13 0.1(2) . . . . ? C10 C11 C12 C15 175.35(13) . . . . ? C11 C12 C13 C14 -0.2(2) . . . . ? C15 C12 C13 C14 -175.12(14) . . . . ? C12 C13 C14 C9 -0.2(2) . . . . ? N6 C9 C14 C13 -178.18(14) . . . . ? C10 C9 C14 C13 0.7(2) . . . . ? C13 C12 C15 O6 175.05(14) . . . . ? C11 C12 C15 O6 0.1(2) . . . . ? C13 C12 C15 N5 -3.5(2) . . . . ? C11 C12 C15 N5 -178.40(13) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.197 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.044 #====END