Nitro­furan­toin methanol monosolvate

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(1)organic compounds Acta Crystallographica Section E. Experimental. Structure Reports Online. Crystal data. ISSN 1600-5368. Nitrofurantoin methanol monosolvate Venu R. Vangala,a* Pui Shan Chowa and Reginald B. H. Tana,b* a. Institute of Chemical and Engineering Sciences, A*STAR (Agency for Science, Technology and Research), 1 Pesek Road, Jurong Island, Singapore 627833, and b Department of Chemical & Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, Singapore 117576 Correspondence e-mail: venugopal_vangala@ices.a-star.edu.sg reginald_tan@ices.a-star.edu.sg Received 28 January 2011; accepted 28 January 2011 ˚; Key indicators: single-crystal X-ray study; T = 110 K; mean (C–C) = 0.003 A R factor = 0.071; wR factor = 0.129; data-to-parameter ratio = 15.6.. ˚3 V = 1128.0 (4) A Z=4 Mo K radiation  = 0.14 mm1 T = 110 K 0.13  0.11  0.11 mm. C8H6N4O5CH4O Mr = 270.21 Monoclinic, P21 =c ˚ a = 6.4084 (13) A ˚ b = 6.5941 (13) A ˚ c = 26.705 (5) A  = 91.70 (3). Data collection 17441 measured reflections 3299 independent reflections 2849 reflections with I > 2(I) Rint = 0.048. Rigaku Saturn 70 CCD areadeterctor diffractometer Absorption correction: multi-scan (CrystalClear; Rigaku, 2008) Tmin = 0.983, Tmax = 0.985. Refinement R[F 2 > 2(F 2)] = 0.071 wR(F 2) = 0.129 S = 1.24 3299 reflections. 212 parameters All H-atom parameters refined ˚ 3 max = 0.24 e A ˚ 3 min = 0.26 e A. Table 1. The antibiotic nitrofurantoin {systematic name: (E)-1-[(5nitro-2-furyl)methylideneamino]imidazolidine-2,4-dione} crystallizes as a methanol monosolvate, C8H6N4O5CH4O. The nitrofurantoin molecule adopts a nearly planar conformation ˚ ). Hydrogen bonds involve the co(r.m.s. deviation = 0.0344 A operative N—H  O—H  O heterosynthons between the cyclic imide of nitrofurantoin and methanol O—H groups. There are also C—H  O hydrogen bonds involving the nitrofurantoin molecules which support the key hydrogenbonding synthon. The overall crystal packing is further assisted by weak C—H  O interactions, giving a herringbone pattern.. Related literature For polymorphism and pseudopolymorphs, see: Bernstein (2002); Byrn et al. (1999); Aitipamula et al. (2010). For nitrofurantoin hydrate and anhydrate crystal structures, see: Otsuka et al. (1991); Pienaar et al. (1993a,b); Bertolasi et al. (1993) and for nitrofurantoin pseudopolymorphs, see: Caira et al. (1996); Tutughamiarso et al. (2011). For a 1:1 co-crystal involving nitrofurantoin and 4-hydroxybenzoic acid, see: Vangala et al. (2011). For hydrogen bonding, see: Desiraju & Steiner (1999); Desiraju (2002, 2007).. ˚ ,  ). Hydrogen-bond geometry (A D—H  A. D—H. H  A. D  A. D—H  A. N4—H4  O6 O6—H6  O5i C5—H5  O4ii C3—H3  O3ii. 0.88 0.86 0.95 0.94. 1.88 1.93 2.22 2.42. 2.755 2.787 3.155 3.176. 170 (3) 172 (3) 169.2 (18) 138 (2). (3) (3) (2) (2). (3) (3) (2) (2). (2) (2) (2) (3). Symmetry codes: (i) x þ 1; y; z; (ii) x  1; y; z.. Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XSEED (Barbour, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).. This work was supported by the Science and Engineering Research Council of A*STAR (Agency for Science, Technology and Research), Singapore. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5112).. References Aitipamula, S., Chow, P. S. & Tan, R. B. H. (2010). Cryst. Growth Des. 10, 2229– 2238. Barbour, L. J. (2001). Supramol. Chem. 1, 189–191. Bernstein, J. (2002). In Polymorphism in Molecular Crystals. Oxford: Clarendon Press. Bertolasi, V., Gilli, P., Ferretti, V. & Gilli, G. (1993). Acta Cryst. C49, 741–744. Byrn, S. R., Pfeiffer, R. R. & Stowell, J. G. (1999). Solid-State Chemistry of Drugs, 2nd ed. West Lafayette, IN, USA: SSCI Inc. Caira, M. R., Pienaar, E. W. & Lo¨tter, A. P. (1996). Mol. Cryst. Liq. Cryst. 279, 241–264. Desiraju, G. R. (2002). Acc. Chem. Res. 35, 565–573. Desiraju, G. R. (2007). Angew. Chem. Int. Ed. 46, 8342–8356. Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, IUCr Monographs on Crystallography, Vol. 9. Oxford University Press.. o550. Vangala et al.. doi:10.1107/S1600536811003679. Acta Cryst. (2011). E67, o550–o551.

(2) organic compounds Otsuka, M., Teraoka, R. & Matsuda, Y. (1991). Pharm. Res. 8, 1066–1068. Pienaar, E. W., Caira, M. R. & Lo¨tter, A. P. (1993a). J. Crystallogr. Spectrosc. Res. 23, 739–744. Pienaar, E. W., Caira, M. R. & Lo¨tter, A. P. (1993b). J. Crystallogr. Spectrosc. Res. 23, 785–790. Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.. Acta Cryst. (2011). E67, o550–o551. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Spek, A. L. (2009). Acta Cryst. D65, 148–155. Tutughamiarso, M., Bolte, M., Wagner, G. & Egert, E. (2011). Acta Cryst. C67, o18–o25. Vangala, V. R., Chow, P. S. & Tan, R. B. H. (2011). CrystEngComm, 13, 759– 762.. Vangala et al.. . C8H6N4O5CH4O. o551.

(3) supporting information. supporting information Acta Cryst. (2011). E67, o550–o551. [doi:10.1107/S1600536811003679]. Nitrofurantoin methanol monosolvate Venu R. Vangala, Pui Shan Chow and Reginald B. H. Tan S1. Comment Polymorphism is an ability of a molecule to exist in two or more crystal structures. Incorporation of solvent molecules into the crystalline lattice are routinely referred to as solvates, inclusion complexes and/or pseudopolymorphs (Bernstein, 2002; Byrn et al., 1999; Aitipamula et al., 2010). A full characterization of various crystal forms of an active pharmaceutical ingredient (API) may reveal desired physical form. Thus, it is relevant to pharmaceutical industry. Nitrofurantoin {(E)-1-[(5-nitro-2-furyl)methylideneamino]imidazoldine-2,4-dione} is an antibacterial agent used in the treatment of genitourinary tract infections. It exists in both anhydrous (α- and β-) and hydrate forms (Forms I and II) (Pienaar et al., 1993a, 1993b; Bertolasi et al., 1993), and literature findings show that nitrofurantoin has poor physical properties (Otsuka et al., 1991; Caira et al., 1996). We have recently reported a 1:1 co-crystal involving nitrofurantoin and 4-hydroxybenzoic acid and shown that co-crystal displayed superior physicochemical and photo-stability to that of nitrofurantoin. However, co-crystallization attempt of nitrofurantoin with fumaric acid in methanol instead yielded the title pseudopolymorph, nitrofurantoin methanol monosolvate. It was reported that this API is known to form inclusion complexes with dimethylformamide, dimethyl sulfoxide and dimethylacetamide (Caira et al., 1996; Tutughamiarso et al., 2011). Herein we report the structural features of a 1:1 pseudopolymorph involving nitrofurantoin and methanol (Fig. 1). Thermogravimetric analysis (TGA traces) of the title compound is shown in Fig. 2. The measured weight loss (11.6% w/w) in the temperature range of 110–140 °C is in agreement with the stoichiometric weight content for a methanol monosolvate (11.8% w/w). Single crystal X-ray diffraction analysis reveals that the crystal structure contains one molecule each of nitrofurantoin and methanol in the asymmetric unit (Fig. 1). It has crystallized in the monoclinic crystal system with P21/c space group. In the structure, nitrofurantoin and methanol molecules were essentially held together by a primary co-operative synthon of N—H···O—H···O [D/Å, θ/°: 2.755 (2), 170 (3); 2.787 (2), 172 (3)] between amide N4—H4, methanolic O6—H6 and imide O5 along the a-axis (Fig. 3). In addition, there are significant C—H···O hydrogen bonds (Desiraju & Steiner 1999; Desiraju 2002; Desiraju 2007) within nitrofurantoin molecules, which lead to ribbons running along a-axis and support the key hydrogen bonding synthon (Fig. 4). It has structural reminiscences with anhydrous nitrofurantoin (β-form), where the packing is stabilized by imide catemer of N—H···O interactions (Pienaar et al., 1993b; Bertolasi et al., 1993). Here, however, it is replaced with N—H···O—H···O catemer type of heterosynthon by retaining a two fold screw axis. Recently, we have noted an identical synthon in a 1:1 co-crystal involving nitrofurantoin and phenolic co-former (4-hydroxybenzoic acid) (Vangala et al., 2011). Hence, supramolecularly methnolic O–H interacted similar to what phenolic O–H is able to do in the reported co-crystal. The overall crystal packing of the title pseudopolymorph is further assisted by weak C—H···O interactions to give a herringbone type of pattern (Fig. 5). Further analysis showed that this herringbone pattern was comparable to that of a crystal structure of nitrofurantoin dimethyl sulfoxide monosolvate (Tutughamiarso et al., 2011).. Acta Cryst. (2011). E67, o550–o551. sup-1.

(4) supporting information S2. Experimental The title psuedopolymorph was obtained by evaporative crystallization during attempts to co-crystallize a commercially available (purchased from Aldrich) nitrofurantoin (β-form, 119 mg, 0.5 mmol) with fumaric acid (58 mg, 0.5 mmol) in methanol (25 ml) at ambient conditions. The yellow needle shaped crystals suitable for single-crystal X-ray diffraction were obtained in three days. S3. Refinement All H atoms bonded to C, N, O atoms were located in a difference map and allowed to ride on their parent atoms in the refinement cycles.. Figure 1 A perspective view showing the molecular structures of nitrofurantoin and methanol, with atom labels and 50% probability displacement ellipsoids for non-H atoms. The dashed line shows the N—H···O hydrogen bond.. Figure 2 TGA traces showed that there was a weight loss of 11.6% (w/w), which can be attributed to a methanol solvate.. Acta Cryst. (2011). E67, o550–o551. sup-2.

(5) supporting information. Figure 3 A partial packing diagram of the title pseudopolymorph is viewed down b-axis, showing formation of the N—H···O— H···O synthon along a-axis. Notice the strong C—H···O hydrogen bonds within nitrofurantoin molecules to support the solid-state structure.. Acta Cryst. (2011). E67, o550–o551. sup-3.

(6) supporting information. Figure 4 A partial packing diagram of the title pseudopolymorph is viewed down b-axis, showing ribbons running along a-axis. Notice the methanol monosolvate showed in space filled style.. Figure 5 Crystal packing of the title pseudopolymorph is viewed down the a-axis, showing a herringbone pattern. Notice also the methanol monosolvate showed in space filled style. (E)-1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dione methanol monosolvate Crystal data C8H6N4O5·CH4O Mr = 270.21 Monoclinic, P21/c a = 6.4084 (13) Å b = 6.5941 (13) Å c = 26.705 (5) Å β = 91.70 (3)° V = 1128.0 (4) Å3 Z=4 F(000) = 560. Acta Cryst. (2011). E67, o550–o551. Dx = 1.591 Mg m−3 Melting point: 547 K Mo Kα radiation, λ = 0.71073 Å Cell parameters from 2901 reflections θ = 1.5–31.2° µ = 0.14 mm−1 T = 110 K Block, yellow 0.13 × 0.11 × 0.11 mm. sup-4.

(7) supporting information Data collection Rigaku Saturn 70 CCD area-deterctor diffractometer Radiation source: fine-focus sealed tube Graphite monochromator ω scans Absorption correction: multi-scan (CrystalClear; Rigaku, 2008) Tmin = 0.983, Tmax = 0.985. 17441 measured reflections 3299 independent reflections 2849 reflections with I > 2σ(I) Rint = 0.048 θmax = 31.2°, θmin = 3.2° h = −6→9 k = −8→9 l = −37→37. Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.071 wR(F2) = 0.129 S = 1.24 3299 reflections 212 parameters 0 restraints Primary atom site location: structure-invariant direct methods. Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites All H-atom parameters refined w = 1/[σ2(Fo2) + (0.033P)2 + 0.7077P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max < 0.001 Δρmax = 0.24 e Å−3 Δρmin = −0.26 e Å−3. Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as 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). O6 C9 H9C H9B H9A H6 O3 N3 O2 C7 N2 N4 C4 C8 C1 C6. x. y. z. Uiso*/Ueq. 0.9997 (2) 0.9409 (4) 0.997 (4) 0.990 (4) 0.786 (4) 1.134 (5) 0.6808 (2) 0.5389 (2) 0.4103 (2) 0.5011 (3) 0.5159 (3) 0.7053 (3) 0.3538 (3) 0.3751 (3) 0.2822 (3) 0.7351 (3). −0.1389 (2) −0.0216 (3) 0.115 (4) −0.085 (4) −0.017 (4) −0.139 (4) 0.3602 (2) 0.0501 (2) 0.4243 (2) −0.0753 (3) 0.1188 (2) −0.0642 (3) 0.3193 (3) −0.0024 (3) 0.2104 (3) 0.0089 (3). 0.22463 (5) 0.18136 (8) 0.1824 (10) 0.1496 (10) 0.1807 (10) 0.2267 (10) 0.58168 (5) 0.36110 (6) 0.62695 (5) 0.28106 (7) 0.40903 (6) 0.29543 (6) 0.54700 (7) 0.32458 (7) 0.47230 (7) 0.34419 (7). 0.0263 (3) 0.0278 (4) 0.042 (7)* 0.039 (7)* 0.047 (8)* 0.046 (8)* 0.0284 (3) 0.0215 (3) 0.0295 (3) 0.0215 (4) 0.0215 (3) 0.0221 (3) 0.0217 (4) 0.0212 (4) 0.0210 (4) 0.0218 (4). Acta Cryst. (2011). E67, o550–o551. sup-5.

(8) supporting information C3 C2 C5 H5 H2 H8B O1 H4 H3 H8A O5 O4 N1. 0.1432 (3) 0.0962 (3) 0.3262 (3) 0.208 (3) −0.034 (4) 0.284 (4) 0.4459 (2) 0.807 (4) 0.053 (4) 0.292 (4) 0.4315 (2) 0.9013 (2) 0.4910 (3). 0.3112 (3) 0.2407 (3) 0.1396 (3) 0.109 (3) 0.218 (3) −0.114 (4) 0.2587 (2) −0.098 (4) 0.348 (4) 0.116 (4) −0.1331 (2) 0.0278 (2) 0.3720 (2). 0.54369 (8) 0.49475 (8) 0.42254 (7) 0.4017 (8) 0.4794 (9) 0.3365 (9) 0.50437 (5) 0.2753 (10) 0.5693 (9) 0.3134 (9) 0.24050 (5) 0.36653 (5) 0.58760 (6). 0.0250 (4) 0.0238 (4) 0.0214 (4) 0.016 (5)* 0.027 (6)* 0.028 (6)* 0.0212 (3) 0.039 (7)* 0.034 (7)* 0.038 (7)* 0.0259 (3) 0.0281 (3) 0.0226 (3). Atomic displacement parameters (Å2). O6 C9 O3 N3 O2 C7 N2 N4 C4 C8 C1 C6 C3 C2 C5 O1 O5 O4 N1. U11. U22. U33. U12. U13. U23. 0.0204 (7) 0.0291 (11) 0.0195 (7) 0.0171 (8) 0.0340 (8) 0.0192 (9) 0.0243 (8) 0.0176 (8) 0.0229 (9) 0.0179 (9) 0.0189 (9) 0.0184 (9) 0.0229 (10) 0.0187 (9) 0.0185 (9) 0.0196 (7) 0.0235 (7) 0.0186 (7) 0.0246 (9). 0.0356 (8) 0.0273 (10) 0.0364 (8) 0.0272 (8) 0.0333 (8) 0.0216 (9) 0.0214 (8) 0.0279 (8) 0.0212 (9) 0.0240 (9) 0.0205 (9) 0.0242 (9) 0.0254 (10) 0.0250 (9) 0.0214 (9) 0.0246 (7) 0.0324 (8) 0.0390 (8) 0.0215 (8). 0.0228 (7) 0.0269 (10) 0.0294 (7) 0.0200 (7) 0.0216 (7) 0.0236 (9) 0.0186 (7) 0.0208 (8) 0.0211 (8) 0.0215 (9) 0.0236 (9) 0.0228 (9) 0.0269 (10) 0.0276 (10) 0.0241 (9) 0.0195 (6) 0.0217 (7) 0.0267 (7) 0.0219 (8). 0.0026 (6) −0.0001 (8) −0.0017 (6) −0.0002 (6) −0.0004 (6) 0.0011 (7) −0.0018 (6) 0.0013 (6) 0.0006 (7) 0.0005 (7) −0.0006 (7) −0.0016 (7) 0.0021 (8) 0.0004 (7) −0.0001 (7) 0.0005 (5) 0.0007 (6) −0.0029 (6) −0.0017 (6). 0.0015 (6) 0.0004 (8) 0.0000 (6) 0.0007 (6) 0.0075 (6) −0.0004 (7) 0.0003 (6) 0.0019 (6) 0.0037 (7) −0.0014 (7) −0.0003 (7) 0.0000 (7) 0.0058 (8) −0.0003 (8) −0.0012 (7) 0.0015 (5) −0.0016 (5) −0.0004 (5) 0.0026 (6). 0.0021 (6) 0.0039 (8) −0.0018 (6) −0.0018 (6) −0.0031 (6) 0.0016 (7) 0.0005 (6) 0.0001 (6) −0.0008 (7) −0.0014 (7) 0.0020 (7) 0.0027 (7) 0.0014 (7) 0.0025 (7) 0.0003 (7) −0.0007 (5) −0.0036 (5) 0.0026 (6) 0.0013 (6). Geometric parameters (Å, º) O6—C9 O6—H6 C9—H9C C9—H9B C9—H9A O3—N1 N3—N2 N3—C6 N3—C8. Acta Cryst. (2011). E67, o550–o551. 1.432 (2) 0.86 (3) 0.97 (3) 1.00 (3) 1.00 (3) 1.234 (2) 1.370 (2) 1.375 (2) 1.454 (2). N4—H4 C4—C3 C4—O1 C4—N1 C8—H8B C8—H8A C1—C2 C1—O1 C1—C5. 0.88 (3) 1.351 (3) 1.358 (2) 1.419 (3) 1.00 (2) 0.99 (3) 1.365 (3) 1.372 (2) 1.444 (3). sup-6.

(9) supporting information O2—N1 C7—O5 C7—N4 C7—C8 N2—C5 N4—C6. 1.234 (2) 1.220 (2) 1.355 (2) 1.513 (3) 1.286 (3) 1.396 (2). C6—O4 C3—C2 C3—H3 C2—H2 C5—H5. 1.212 (2) 1.411 (3) 0.94 (2) 0.93 (2) 0.95 (2). C9—O6—H6 O6—C9—H9C O6—C9—H9B H9C—C9—H9B O6—C9—H9A H9C—C9—H9A H9B—C9—H9A N2—N3—C6 N2—N3—C8 C6—N3—C8 O5—C7—N4 O5—C7—C8 N4—C7—C8 C5—N2—N3 C7—N4—C6 C7—N4—H4 C6—N4—H4 C3—C4—O1 C3—C4—N1 O1—C4—N1 N3—C8—C7 N3—C8—H8B C7—C8—H8B. 107.0 (19) 112.9 (16) 112.2 (15) 106 (2) 105.6 (16) 110 (2) 109 (2) 119.80 (15) 127.60 (15) 112.43 (15) 126.39 (18) 126.25 (17) 107.36 (16) 115.25 (16) 112.76 (16) 122.4 (17) 124.8 (17) 113.05 (17) 130.92 (18) 115.98 (16) 101.52 (15) 112.3 (14) 110.1 (14). N3—C8—H8A C7—C8—H8A H8B—C8—H8A C2—C1—O1 C2—C1—C5 O1—C1—C5 O4—C6—N3 O4—C6—N4 N3—C6—N4 C4—C3—C2 C4—C3—H3 C2—C3—H3 C1—C2—C3 C1—C2—H2 C3—C2—H2 N2—C5—C1 N2—C5—H5 C1—C5—H5 C4—O1—C1 O2—N1—O3 O2—N1—C4 O3—N1—C4. 112.7 (15) 108.3 (15) 111.3 (19) 110.68 (17) 130.44 (18) 118.88 (16) 128.06 (18) 126.05 (18) 105.89 (16) 104.99 (17) 125.3 (16) 129.7 (16) 106.88 (18) 124.4 (15) 128.8 (15) 120.33 (17) 124.0 (13) 115.7 (13) 104.40 (14) 124.47 (17) 116.97 (16) 118.54 (16). Hydrogen-bond geometry (Å, º) D—H···A. D—H. H···A. D···A. D—H···A. N4—H4···O6 O6—H6···O5i C5—H5···O4ii C3—H3···O3ii. 0.88 (3) 0.86 (3) 0.95 (2) 0.94 (2). 1.88 (3) 1.93 (3) 2.22 (2) 2.42 (2). 2.755 (2) 2.787 (2) 3.155 (2) 3.176 (3). 170 (3) 172 (3) 169.2 (18) 138 (2). Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.. Acta Cryst. (2011). E67, o550–o551. sup-7.

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Crystal structure of bromido fac tricarbon­yl[5 (3,4,5 tri­meth­­oxy­phen­yl) 3 (pyridin 2 yl) 1H 1,2,4 triazole κ2N2,N3]rhenium(I) methanol monosolvate
a Part of the crystal structure of the title complex, showing dimers formed by conventional hydrogen bonding involving the methanol solvent molecules and weak C—H O interactions
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Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acryl­amide
Refinement Figure 3 A view along the b axis of the crystal packing of the title compound, showing the -sheet arrangement formed through strong N—H O hydrogen bonds dashed lines; see
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Crystal structure of 1,2,3,4 di O methyl­ene α D galacto­pyran­ose
Figure 2 O—H···O hydrogen bonds black dashed lines between adjacent molecules in the crystal structure of the title compound ac view... Figure 3 C—H···O and O—H···O hydrogen
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Crystal structures of three co crystals of 4,4′ bi­pyridyl with 4 alk­­oxy­benzoic acids: 4 eth­­oxy­benzoic acid–4,4′ bi­pyridyl (2/1), 4 n propoxybenzoic acid–4,4′ bi­pyridyl (2/1) and 4 n but­­oxy­benzoic acid–4,4′ bi­pyridyl (2/1)
Figure 4 A partial packing diagram of compound I, showing the sheet structure formed by O—H N and C—H O hydrogen bonds dashed lines.. H atoms not involved in the hydrogen bonds have
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Crystal structure of (2 amino 7 methyl 4 oxido­pteridine 6 carboxyl­ato κ3O4,N5,O6)aqua­(1,10 phenanthroline κ2N,N′)copper(II) trihydrate
In the crystal, N—H O, O—H N and O—H O hydrogen bonds, as well as weak C—H O hydrogen bonds and C—H interactions, link the complex molecules and lattice water molecules into a
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Crystal structure of ethyl (2Z) 2 cyano 3 [(3 methyl 1 phenyl 1H pyrazol 5 yl)amino]­prop 2 enoate
Figure 3 Packing showing the layer structure with intramolecular N—H···O hydrogen bonds shown as blue dotted lines and intermolecular C—H···O and C—H···N interactions as red
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Crystal structure of (E) 1(anthracen 9 ylmethyl­idene)[2 (morpholin 4 yl)eth­yl]amine
In the crystal, the packing is stabilized by weak C—H O hydrogen bonds, which connect pairs of molecules into parallel to the c axis, and C—H interactions... Keywords: crystal
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Di­ethyl 4 (bi­phenyl 4 yl) 2,6 di­methyl 1,4 di­hydro­pyridine 3,5 di­carboxyl­ate
Figure 3 Packing diagram of the title compound, showing intermolecular C – H ··· O interactions in dashed lines which cross link the molecules into a sheet motif running slightly off
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1 Piperonylpiperazinium 4 nitro­benzoate monohydrate
The crystal packing is stabilized by these N—H···O and O—H···O intermolecular hydrogen bonds and weak C—H···O intermolecular interactions Table 1 involving the water molecules
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4 Meth­­oxy N [(4 methyl­phen­yl)sulfon­yl]benzamide including an unknown solvate
Figure 4 A view of the C—H···O hydrogen bonds linking molecules to form C5 chains in the crystal structure of the title compound see Table 1 for details; H atoms not involved in these
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catena Poly[[[aqua­(glycine κO)lithium] μ glycine κ2O:O′] bromide]
Figure 3 A partial view of the crystal structure of the title complex, showing the hydrogen bonds involving the glycine molecules.... Figure 4 Part of the crystal structure showing
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(2Z,2′Z) Di­ethyl 3,3′ [butane 1,4 diylbis(aza­nedi­yl)]bis­­(but 2 enoate)
Figure 2 A view along the a axis of the crystal packing of the title compound, showing the N—H···O and C—H···O hydrogen bonds as dashed cyan lines.. Data collection Stoe IPDS 2
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