In the structure of the title compound, CH6N3+ . C8H4NO6- . H2O, obtained from the reaction of guanidine carbonate with 3-nitrophthalic acid, the 2-carboxylic acid group is deprotonated and participates in an asymmetric cyclic R2/1(6) hydrogen-bonding associatiuon with the guanidine cation together with a bridging water molecule of solvation. A conjoint R2/1(7) facial association involving a nitro O-atom acceptor together with a further five guanidinium N-H...O hydrogen bonds, as well as a strong carboxyl-water interaction [2.528(3) Ang.], give a two-dimensiional network structure

Healy, Peter

Smith, Graham

Wermuth, Urs

Acta Crystallographica Section E

English

In the structure of the title compound, CH6N3+烸H4NO6-爲O, obtained from the reaction of guanidine carbonate with 3-nitrophthalic acid, the 2-carboxylic acid group is deprotonated and participates in an asymmetric cyclic R21(6) hydrogen-bonding association with the guanidine cation together with a bridging water molecule of solvation. A conjoint R12(7) facial association involving a nitro O-atom acceptor together with a further five guanidinium N-H...O hydrogen bonds, as well as a strong carboxyl-water O-H...O interaction [2.528 (3) ŝ, give a two-dimensional network structure.Full Tex

D. Wermuth, Urs

Griffith Research Online

Guanidinium 2-carboxy-6-nitrobenzoatemonohydrate: a two-dimensionalhydrogen-bonded network structureGraham Smith,a* Urs D. Wermutha and Peter C. HealybaSchool of Physical and Chemical Sciences, Queensland University of Technology,GPO Box 2434, Brisbane, Queensland 4001, Australia, and bSchool of Biomolecularand Physical Sciences, Griffith University, Nathan, Queensland 4111, AustraliaCorrespondence e-mail: g.smith@qut.edu.auReceived 11 July 2007; accepted 13 July 2007Key indicators: single-crystal X-ray study; T = 297 K; mean (C–C) = 0.003 A˚;R factor = 0.047; wR factor = 0.147; data-to-parameter ratio = 13.2.In the structure of the title compound, CH6N3+-C8H4NO6H2O, obtained from the reaction of guanidinecarbonate with 3-nitrophthalic acid, the 2-carboxylic acidgroup is deprotonated and participates in an asymmetric cyclicR21(6) hydrogen-bonding association with the guanidine cationtogether with a bridging water molecule of solvation. Aconjoint R12(7) facial association involving a nitro O-atomacceptor together with a further five guanidinium N—H  Ohydrogen bonds, as well as a strong carboxyl–water O—H  Ointeraction [2.528 (3) A˚], give a two-dimensional networkstructure.Related literatureFor related literature, see: Bernstein et al. (1995); Glidewell etal. (2003, 2005); Guo (2004); Smith et al. (2001, 2005); Smith,Wermuth & White (2007); Smith, Wermuth, Healy & White(2007).ExperimentalCrystal dataCH6N3+C8H4NO6H2OMr = 288.23Monoclinic, P21=ca = 14.758 (3) A˚b = 12.5955 (19) A˚c = 6.8423 (12) A˚ = 100.006 (16)V = 1252.5 (4) A˚3Z = 4Mo K radiation = 0.13 mm1T = 297 (2) K0.40  0.35  0.20 mmData collectionRigaku AFC-7R diffractometerAbsorption correction:  scan(TEXSAN for Windows;Molecular StructureCorporation, 1999)Tmin = 0.949, Tmax = 0.9743307 measured reflections2872 independent reflections2080 reflections with I > 2(I)Rint = 0.0283 standard reflectionsfrequency: 150 minintensity decay: 1.2%RefinementR[F 2 > 2(F 2)] = 0.047wR(F 2) = 0.147S = 0.862872 reflections217 parametersH atoms treated by a mixture ofindependent and constrainedrefinementmax = 0.33 e A˚3min = 0.40 e A˚3Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AO1W—H1W  O21B 0.88 (5) 1.90 (5) 2.777 (3) 176 (3)O1W—H2W  O21Ai 0.85 (5) 1.91 (5) 2.764 (3) 173 (4)O11A—H11A  O1W ii 0.89 (4) 1.65 (4) 2.528 (3) 169 (4)N12—H12A  O21Aiii 0.91 (4) 2.06 (4) 2.946 (3) 167 (3)N12—H12B  O21B 0.85 (4) 2.58 (4) 3.286 (3) 141 (3)N12—H12B  O31A 0.85 (4) 2.51 (3) 2.964 (3) 114 (3)N22—H22A  O11Biv 0.91 (4) 1.96 (4) 2.846 (3) 162 (3)N22—H22B  O21Bv 0.87 (4) 2.54 (3) 3.183 (3) 132 (3)N32—H32A  O21B 0.83 (3) 2.11 (3) 2.905 (3) 162 (3)N32—H32B  O11Biv 0.85 (4) 2.51 (4) 3.152 (3) 134 (3)N32—H32B  O21Aiv 0.85 (4) 2.30 (4) 3.048 (3) 148 (3)Symmetry codes: (i) x; y; zþ 1; (ii) x;yþ 52; z 12; (iii) x;yþ 32; zþ 12; (iv)x;y þ 2;zþ 1; (v) x; y 12;zþ 32.Data collection: MSC/AFC Diffractometer Control Software(Molecular Structure Corporation, 1999); cell refinement: MSC/AFCDiffractometer Control Software; data reduction: TEXSAN forWindows (Molecular Structure Corporation, 1999); program(s) usedto solve structure: SIR92 (Altomare et al., 1994); program(s) used torefine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:PLATON (Spek, 2003); software used to prepare material forpublication: PLATON.The authors acknowledge financial support from the Schoolof Physical and Chemical Sciences, Queensland University ofTechnology, and the School of Biomolecular and PhysicalSciences, Griffith University.Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: WN2170).ReferencesAltomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C.,Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.Int. Ed. Engl. 34, 1555–1573.Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst.C59, o509–o511.Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst.C61, o246–o248.Guo, M.-L. (2004). Acta Cryst. E60, o1236–o1238.Molecular Structure Corporation (1999). MSC/AFC Diffractometer ControlSoftware and TEXSAN for Windows (Version 1.06). MSC, The Woodlands,Texas, USA.Sheldrick, G. M. (1997). SHELXL97. University of Go¨ttingen, Germany.Smith, G., Bott, R. C. & Wermuth, U. D. (2001). Acta Cryst. E57, o640–o642.organic compoundsActa Cryst. (2007). E63, o3527–o3528 doi:10.1107/S1600536807034356 # 2007 International Union of Crystallography o3527Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368Smith, G., Wermuth, U. D., Healy, P. C. & White, J. M. (2007). Acta Cryst. E63,o7–o9.Smith, G., Wermuth, U. D. & White, J. M. (2007). Acta Cryst. E63, o867–o868.Smith, G., Wermuth, U. D., Young, D. J. & Healy, P. C. (2005). Acta Cryst. E61,o2008–o2011.Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.organic compoundso3528 Smith et al.  CH6N3+C8H4NO6H2O Acta Cryst. (2007). E63, o3527–o3528supplementary materialssupplementary materialssup-1Acta Cryst. (2007). E63, o3527-o3528    [ doi:10.1107/S1600536807034356 ]Guanidinium 2-carboxy-6-nitrobenzoate monohydrate: a two-dimensional hydrogen-bonded net-work structureG. Smith, U. D. Wermuth and P. C. HealyCommentThe structures of the guanidinium salts of nitro-substituted benzoic acids are not numerous in the crystallographic literature.Among these are the 1:1 anhydrous guanidinium salts of 3,5-dinitrosalicylic acid (Smith et al., 2001), 3,5-dinitrobenzoicacid (Smith, Wermuth & White, 2007) and 4-nitroanthranilic acid (a monohydrate) (Smith et al., 2007). The nitro-substitutedaromatic dicarboxylic acids provide additional potential for structure extension and some structures of 1:1 Lewis base saltsof these acids are known, e.g. the anhydrous compounds of 3-nitrophthalic acid with 3-iodoaniline (Glidewell et al.. 2005)and 4-iodoaniline (Glidewell et al.. 2003 and the dihydrate with brucine (Smith et al., 2005). In the 1:1 dihydrate salt withpiperazine (Guo, 2004), the phthalate species is dianionic.Our 1:1 stoichiometric reaction of 3-nitrophthalic acid with guanidinium carbonate in methanol surprisingly gave goodcrystals of a hydrated salt guanidinium 2-carboxy-6-nitrobenzoate monohydrate, CH6N3+·C8H4NO6−·H2O, which is re-ported here. In the title compound, the usual proton transfer occurs from the central (C2) carboxylic acid group which isthen involved in a direct hydrogen-bonding interaction with a guanidinium proton (Fig. 1). The guanidinium protons areinvolved in eight hydrogen bonds with all but one of the available O acceptors (nitro O31B) (Table 1). These include thewater molecule of solvation which also provides a bridging link between the two separate carboxylate O-acceptors (O21Ai,O21B: symmetry code (i), x, y, z + 1], extending the structure down the c cell direction. With the guanidinium cation thereis an asymmetric cyclic R21(6) (Bernstein et al., 1995) interaction also with a carboxylate O-acceptor together with a con-joint R12(7) nitro-O interaction. The carboxylic acid proton gives a strong hydrogen bond with the water molecule [O···O,2.528 (2) Å], the overall result being a two-dimensional network structure (Fig. 2).Within the 3-nitrophthalate anion, the carboxylate group is close to perpendicular to the plane of the benzene ring[C1—C2—C21—O21A, 101.2 (2)°], while the carboxylic acid group is close to coplanar [C2—C1—C11—O11A,173.34 (19)°]. The nitro group is intermediate between these [C2—3—N31—O31B, 151.2 (2) °]. This conformation is sim-ilar to that found in other acid salts of 3-nitrophthalic acid (Smith et al., 2005; Glidewell et al. 2003, 2005). In addition thereis an intramolecular aromatic ring hydrogen bond [C6–H···O11A: 2.706 (3) Å] associated with the carboxylic acid group.ExperimentalThe title compound was synthesized by heating together 1 mmol quantities of 3-nitrophthalic acid and guanidine carbonatein 50 ml of methanol under reflux for 10 minutes. After concentration to ca 30 ml, partial room temperature evaporation ofthe hot-filtered solution gave colourless crystal prisms (m.p. 395–396 K).supplementary materialssup-2RefinementHydrogen atoms involved in hydrogen-bonding interactions were located by difference methods and their positional andisotropic displacement parameters were refined. The ranges of refined bond lengths were N—H = 0.83 (3)–0.91 (4) Å andO—H = 0.85 (5)–0.89 (4) Å. The aromatic H atoms were included in the refinement in calculated positions (C—H = 0.95Å) using a riding model approximation, with Uiso(H) = 1.2Ueq(C).FiguresFig. 1. Molecular configuration and atom naming scheme for the guanidinium cation, the 3-nitrophthalate anion and the water molecule of solvation in the title compound. Displacementellipsoids are drawn at the 40% probability level. Dashed lines indicate hydrogen bonds.Fig. 2. The hydrogen-bonded framework structure of the title compound, viewed down the caxial direction, showing hydrogen-bonding associations as dashed lines. For symmetry codes,see Table 1.guanidinium 2-carboxy-6-nitrobenzoate monohydrateCrystal dataCH6N3+·C8H4NO6–·H2O F000 = 600Mr = 288.23 Dx = 1.528 Mg m−3Monoclinic, P21/c Melting point: 395-396 KHall symbol: -P 2ybc Mo Kα radiationλ = 0.71073 Åa = 14.758 (3) Å Cell parameters from 25 reflectionsb = 12.5955 (19) Å θ = 12.6–17.5ºc = 6.8423 (12) Å µ = 0.13 mm−1β = 100.006 (16)º T = 297 (2) KV = 1252.5 (4) Å3 Cut block, colourlessZ = 4 0.40 × 0.35 × 0.20 mmData collectionRigaku AFC-7Rdiffractometer Rint = 0.028Radiation source: rotating anode θmax = 27.5ºMonochromator: graphite θmin = 2.8ºT = 297(2) K h = −18→19supplementary materialssup-3ω/2θ scans k = 0→16Absorption correction: ψ scan(TEXSAN for Windows; Molecular Structure Cor-poration, 1999)l = −8→3Tmin = 0.949, Tmax = 0.974 3 standard reflections3307 measured reflections every 150 min2872 independent reflections intensity decay: 1.2%2080 reflections with I > 2σ(I)RefinementRefinement on F2 Secondary atom site location: difference Fourier mapLeast-squares matrix: full Hydrogen site location: inferred from neighbouringsitesR[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture ofindependent and constrained refinementwR(F2) = 0.147  w = 1/[σ2(Fo2) + (0.1P)2 + 5.5554P]where P = (Fo2 + 2Fc2)/3S = 0.86 (Δ/σ)max = 0.0012872 reflections Δρmax = 0.33 e Å−3217 parameters Δρmin = −0.40 e Å−3Primary atom site location: structure-invariant directmethods Extinction correction: noneSpecial detailsGeometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from thevariances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and tor-sion anglesRefinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, convention-al R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculat-ing R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twiceas large as those based on F, and R– factors based on ALL data will be even larger.Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)x y z Uiso*/UeqO11A 0.33502 (12) 1.28306 (13) 0.6829 (3) 0.0402 (6)O11B 0.21101 (11) 1.19235 (14) 0.5452 (3) 0.0436 (6)O21A 0.16688 (11) 0.96584 (13) 0.4120 (2) 0.0331 (5)O21B 0.16155 (10) 0.98708 (14) 0.7330 (2) 0.0339 (5)O31A 0.25485 (12) 0.78120 (15) 0.6336 (3) 0.0480 (6)O31B 0.38515 (13) 0.73913 (16) 0.5523 (3) 0.0551 (7)N31 0.33335 (13) 0.80279 (15) 0.6115 (3) 0.0338 (6)C1 0.34791 (14) 1.09732 (17) 0.6688 (3) 0.0266 (6)C2 0.30745 (13) 0.99645 (16) 0.6370 (3) 0.0240 (5)C3 0.36807 (14) 0.91080 (17) 0.6560 (3) 0.0270 (6)supplementary materialssup-4C4 0.46275 (15) 0.92106 (19) 0.7140 (4) 0.0337 (7)C5 0.50006 (15) 1.0204 (2) 0.7553 (4) 0.0374 (7)C6 0.44276 (15) 1.10785 (19) 0.7288 (4) 0.0346 (7)C11 0.29065 (15) 1.19500 (17) 0.6278 (3) 0.0283 (6)C21 0.20296 (13) 0.98198 (16) 0.5881 (3) 0.0250 (6)N12 0.08940 (15) 0.7473 (2) 0.8170 (3) 0.0406 (7)N22 −0.05841 (16) 0.6993 (2) 0.6799 (4) 0.0454 (7)N32 −0.01159 (16) 0.87191 (19) 0.6668 (4) 0.0409 (7)C12 0.00621 (15) 0.77276 (19) 0.7218 (3) 0.0313 (6)O1W 0.25121 (17) 1.04247 (17) 1.1102 (4) 0.0536 (7)H4 0.50130 0.86020 0.72510 0.0400*H5 0.56420 1.02870 0.80120 0.0450*H6 0.46850 1.17680 0.75190 0.0420*H11A 0.299 (3) 1.340 (3) 0.655 (5) 0.069 (11)*H12A 0.104 (2) 0.678 (3) 0.838 (5) 0.055 (9)*H12B 0.130 (2) 0.796 (3) 0.839 (5) 0.056 (10)*H22A −0.113 (3) 0.720 (3) 0.605 (6) 0.071 (11)*H22B −0.050 (2) 0.637 (3) 0.733 (5) 0.056 (9)*H32A 0.030 (2) 0.917 (3) 0.683 (5) 0.058 (10)*H32B −0.066 (3) 0.894 (3) 0.629 (5) 0.063 (10)*H1W 0.222 (3) 1.022 (3) 0.994 (7) 0.071 (12)*H2W 0.221 (3) 1.018 (3) 1.196 (7) 0.078 (13)*Atomic displacement parameters (Å2)U11 U22 U33 U12 U13 U23O11A 0.0312 (9) 0.0252 (8) 0.0599 (12) 0.0003 (7) −0.0037 (8) −0.0040 (8)O11B 0.0257 (8) 0.0321 (9) 0.0679 (12) 0.0020 (7) −0.0064 (8) 0.0011 (8)O21A 0.0271 (8) 0.0384 (9) 0.0304 (8) −0.0047 (7) −0.0042 (6) −0.0010 (7)O21B 0.0254 (8) 0.0420 (9) 0.0352 (9) −0.0050 (7) 0.0077 (6) −0.0025 (7)O31A 0.0332 (9) 0.0341 (9) 0.0750 (14) −0.0063 (7) 0.0045 (9) −0.0017 (9)O31B 0.0406 (10) 0.0408 (10) 0.0789 (15) 0.0122 (8) −0.0036 (10) −0.0200 (10)N31 0.0288 (9) 0.0273 (9) 0.0407 (11) 0.0034 (8) −0.0069 (8) −0.0018 (8)C1 0.0206 (9) 0.0274 (10) 0.0309 (11) 0.0001 (8) 0.0019 (8) 0.0003 (8)C2 0.0200 (9) 0.0279 (10) 0.0232 (9) −0.0004 (7) 0.0015 (7) −0.0008 (8)C3 0.0232 (10) 0.0267 (10) 0.0294 (10) 0.0007 (8) −0.0004 (8) −0.0009 (8)C4 0.0218 (10) 0.0343 (12) 0.0427 (13) 0.0058 (9) −0.0008 (9) 0.0025 (10)C5 0.0187 (9) 0.0401 (13) 0.0510 (14) 0.0000 (9) −0.0008 (9) 0.0020 (11)C6 0.0246 (10) 0.0307 (11) 0.0462 (13) −0.0047 (9) −0.0004 (9) 0.0000 (10)C11 0.0269 (10) 0.0262 (10) 0.0316 (11) −0.0008 (8) 0.0045 (8) −0.0002 (8)C21 0.0200 (9) 0.0217 (9) 0.0321 (11) 0.0003 (7) 0.0011 (8) 0.0004 (8)N12 0.0273 (10) 0.0456 (13) 0.0464 (12) 0.0044 (10) −0.0008 (9) 0.0084 (10)N22 0.0350 (11) 0.0429 (13) 0.0551 (14) −0.0070 (10) −0.0011 (10) 0.0137 (11)N32 0.0274 (10) 0.0376 (12) 0.0559 (14) 0.0050 (9) 0.0026 (9) 0.0080 (10)C12 0.0251 (10) 0.0376 (12) 0.0312 (11) 0.0023 (9) 0.0047 (8) 0.0055 (9)O1W 0.0732 (15) 0.0483 (12) 0.0396 (11) −0.0297 (11) 0.0107 (11) −0.0049 (9)supplementary materialssup-5Geometric parameters (Å, °)O11A—C11 1.310 (3) N22—H22B 0.87 (4)O11B—C11 1.213 (3) N22—H22A 0.91 (4)O21A—C21 1.247 (2) N32—H32B 0.85 (4)O21B—C21 1.253 (2) N32—H32A 0.83 (3)O31A—N31 1.225 (3) C1—C6 1.395 (3)O31B—N31 1.224 (3) C1—C11 1.491 (3)O11A—H11A 0.89 (4) C1—C2 1.405 (3)O1W—H1W 0.88 (5) C2—C3 1.393 (3)O1W—H2W 0.85 (5) C2—C21 1.531 (3)N31—C3 1.467 (3) C3—C4 1.391 (3)N12—C12 1.325 (3) C4—C5 1.376 (3)N22—C12 1.324 (3) C5—C6 1.381 (3)N32—C12 1.318 (3) C4—H4 0.9500N12—H12B 0.85 (4) C5—H5 0.9500N12—H12A 0.91 (4) C6—H6 0.9500C11—O11A—H11A 112 (3) N31—C3—C4 116.29 (19)H1W—O1W—H2W 107 (4) N31—C3—C2 120.22 (18)O31A—N31—C3 118.95 (19) C3—C4—C5 119.3 (2)O31A—N31—O31B 123.6 (2) C4—C5—C6 119.0 (2)O31B—N31—C3 117.41 (19) C1—C6—C5 121.5 (2)C12—N12—H12B 118 (2) O11A—C11—O11B 123.6 (2)C12—N12—H12A 119 (2) O11A—C11—C1 113.95 (19)H12A—N12—H12B 122 (3) O11B—C11—C1 122.4 (2)H22A—N22—H22B 123 (3) O21A—C21—C2 118.40 (18)C12—N22—H22A 117 (2) O21B—C21—C2 115.60 (17)C12—N22—H22B 120 (2) O21A—C21—O21B 126.01 (19)H32A—N32—H32B 117 (3) C3—C4—H4 120.00C12—N32—H32B 122 (3) C5—C4—H4 120.00C12—N32—H32A 120 (2) C6—C5—H5 121.00C2—C1—C6 120.6 (2) C4—C5—H5 121.00C6—C1—C11 118.9 (2) C5—C6—H6 119.00C2—C1—C11 120.35 (19) C1—C6—H6 119.00C3—C2—C21 122.30 (18) N12—C12—N22 120.6 (2)C1—C2—C3 115.93 (18) N12—C12—N32 119.4 (2)C1—C2—C21 121.77 (18) N22—C12—N32 120.0 (2)C2—C3—C4 123.5 (2)O31A—N31—C3—C2 −28.2 (3) C6—C1—C11—O11B 167.8 (2)O31A—N31—C3—C4 152.5 (2) C1—C2—C3—N31 −175.49 (18)O31B—N31—C3—C2 151.2 (2) C1—C2—C3—C4 3.7 (3)O31B—N31—C3—C4 −28.0 (3) C21—C2—C3—N31 5.6 (3)C6—C1—C2—C3 −4.2 (3) C21—C2—C3—C4 −175.3 (2)C6—C1—C2—C21 174.8 (2) C1—C2—C21—O21A 101.2 (2)C11—C1—C2—C3 172.36 (18) C1—C2—C21—O21B −79.2 (3)C11—C1—C2—C21 −8.7 (3) C3—C2—C21—O21A −79.9 (3)C2—C1—C6—C5 1.2 (4) C3—C2—C21—O21B 99.7 (2)C11—C1—C6—C5 −175.4 (2) N31—C3—C4—C5 179.1 (2)supplementary materialssup-6C2—C1—C11—O11A 173.34 (19) C2—C3—C4—C5 −0.1 (4)C2—C1—C11—O11B −8.8 (3) C3—C4—C5—C6 −3.1 (4)C6—C1—C11—O11A −10.1 (3) C4—C5—C6—C1 2.5 (4)Hydrogen-bond geometry (Å, °)D—H···A D—H H···A D···A D—H···AO1W—H1W···O21B 0.88 (5) 1.90 (5) 2.777 (3) 176 (3)O1W—H2W···O21Ai 0.85 (5) 1.91 (5) 2.764 (3) 173 (4)O11A—H11A···O1Wii 0.89 (4) 1.65 (4) 2.528 (3) 169 (4)N12—H12A···O21Aiii 0.91 (4) 2.06 (4) 2.946 (3) 167 (3)N12—H12B···O21B 0.85 (4) 2.58 (4) 3.286 (3) 141 (3)N12—H12B···O31A 0.85 (4) 2.51 (3) 2.964 (3) 114 (3)N22—H22A···O11Biv 0.91 (4) 1.96 (4) 2.846 (3) 162 (3)N22—H22B···O21Bv 0.87 (4) 2.54 (3) 3.183 (3) 132 (3)N32—H32A···O21B 0.83 (3) 2.11 (3) 2.905 (3) 162 (3)N32—H32B···O11Biv 0.85 (4) 2.51 (4) 3.152 (3) 134 (3)N32—H32B···O21Aiv 0.85 (4) 2.30 (4) 3.048 (3) 148 (3)C4—H4···O11Avi 0.9500 2.5800 3.420 (3) 148.00C6—H6···O11A 0.9500 2.3600 2.706 (3) 101.00C6—H6···O31Bvii 0.9500 2.4600 3.179 (3) 132.00Symmetry codes: (i) x, y, z+1; (ii) x, −y+5/2, z−1/2; (iii) x, −y+3/2, z+1/2; (iv) −x, −y+2, −z+1; (v) −x, y−1/2, −z+3/2; (vi) −x+1, y−1/2,−z+3/2; (vii) −x+1, y+1/2, −z+3/2.supplementary materialssup-7Fig. 1supplementary materialssup-8Fig. 2

Guanidinium 2-Carboxy-6-Nitrobenzoate Monohydrate: A Two-Dimensional Hydrogen-Bonded Network Structure

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