Synthesis and crystal structure of (E)-2-({2-[aza-niumyl-idene(methyl-sulfan-yl)meth-yl]hydrazinyl-idene}meth-yl)benzene-1,4-diol hydrogen sulfate.
Journal: 2019/November - Acta Crystallographica Section E: Crystallographic Communications
ISSN: 2056-9890
Abstract:
The title mol-ecular salt, C9H12N3O2S+·HSO4-, was obtained through the protonation of the azomethine N atom in a sulfuric acid medium. The crystal com-prises two entities, a thio-semicarbazide cation and a hydrogen sulfate anion. The cation is essentially planar and is further stabilized by a strong intra-molecular O-H⋯N hydrogen bond. In the crystal, a three-dimensional network is established through O-H⋯O and N-H⋯O hydrogen bonds. A weak intermolecular C-H⋯O hydrogen bond is also observed. The hydrogen sulfate anion exhibits disorder over two sets of sites and was modelled with refined occupancies of 0.501 (6) and 0.499 (6).
Relations:
Content
Chemicals
(2)
Genes
(3)
Processes
(1)
Similar articles
Articles by the same authors
Discussion board
Acta Crystallogr E Crystallogr Commun 75(Pt 11): 1738-1740

Synthesis and crystal structure of (<em>E</em>)-2-({2-[aza­niumyl­idene(methyl­sulfan­yl)meth­yl]hydrazinyl­idene}meth­yl)benzene-1,4-diol hydrogen sulfate

Chemical context

Thio­semicarbazones and their com­plexes are well known for their pharmacological properties, as anti­microbial (Plech et al., 2011; Pandeya et al., 1999; Küçükgüzel et al., 2006), anti-inflammatory (Palaska et al., 2002) and anti­umoural (de Oliveira et al., 2015) agents. Complexes of thio­semicarbazones are studied in the literature as drug candidates, biomarkers and biocatalysts (Hayne et al., 2014; Lim et al., 2010). It is believed that the biological activity of these com­pounds has a strong relationship with the nature of the aldehydes and ketones from which those thio­semicarbazones were obtained (Teoh et al., 1999), and also on the substituents attached at the NH2 N atom (Beraldo &amp; Gambino, 2004). An inter­esting attribute of thio­semicarbazones is their ability to exhibit thione–thiol tautomerism and they can also exist as E and Z isomers. Thio­semicarbazones have an excellent capacity to com­plex transition metals, acting as chelating agents; this process usually takes place via dissociation of the acidic proton (Pal et al., 2002). The crystal structure of the title mol­ecular salt was determined in order to investigate its biological and catalytic activities.

Structural commentary

The mol­ecular structure of the title mol­ecular salt is illustrated in Fig. 1. It com­prises two entities, i.e. a thio­semicarbazone cation and a hydrogen sulfate anion. The cation is essentially planar and shows an E conformation with regard to the C6—N5 bond, the maximum deviation from the mean plane through the 15 non-H atoms being 0.1 (2) Å for atom C6. This planarity is due to electron delocalization along the cation backbone, which is further stabilized by an intra­molecular O13—H13⋯N5 hydrogen bond (Zhu et al., 2004). The bond lengths and angles resemble those observed for similar thio­semicarbazone derivatives (Gangadharan et al., 2015; Joseph et al., 2004; Nehar et al., 2016; Houari et al., 2013). The anion (hydrogen sulfate) is disordered, split over two sets of siteswith relative occupancies of 0.501 (6) and 0.499 (6), and labelled with A and B suffixes.

An external file that holds a picture, illustration, etc.
Object name is e-75-01738-scheme1.jpg

An external file that holds a picture, illustration, etc.
Object name is e-75-01738-fig1.jpg

The mol­ecular structure of the title mol­ecular salt, showing the labelling and with displacement ellipsoids drawn at the 50% probability level. The disordered hydrogen sulfate anion is shown.

Supra­molecular features

In the crystal, the three-dimensional structure is established through an extensive network of O—H⋯O and N—H⋯O hydrogen bonds. Also within this network exists a weak C—H⋯O inter­molecular hydrogen bond (Table 1 and Fig. 2). The crystal packing is shown in Fig. 2.

An external file that holds a picture, illustration, etc.
Object name is e-75-01738-fig2.jpg

Projection along the a axis of the crystal packing of the title mol­ecular salt. Hydrogen bonds are shown as dashed lines.

Table 1

Hydrogen-bond geometry (Å, °)
D—H⋯AD—HH⋯ADAD—H⋯A
C10—H10⋯O12A0.952.603.541 (10)170
N3—H3A⋯O12A0.89 (2)1.85 (2)2.738 (12)178 (3)
N3—H3A⋯O12B0.89 (2)1.98 (2)2.841 (11)163 (3)
N3—H3B⋯O140.86 (2)2.05 (2)2.874 (3)160 (3)
N4—H4⋯O13A0.86 (3)2.00 (3)2.849 (5)167 (3)
N4—H4⋯O13B0.86 (3)2.00 (3)2.841 (5)164 (3)
O13—H13⋯N50.78 (3)2.03 (3)2.685 (3)142 (3)
O14—H14⋯O11A0.83 (4)1.90 (4)2.716 (16)167 (3)
O14—H14⋯O11B0.83 (4)1.82 (4)2.62 (2)162 (3)
O14A—H14A⋯O11A0.842.283.123 (17)180
O14B—H14B⋯S2B0.842.733.490 (9)152
O14B—H14B⋯O13B0.841.732.567 (7)180

Symmetry codes: (i) An external file that holds a picture, illustration, etc.
Object name is e-75-01738-efi1.jpg; (ii) An external file that holds a picture, illustration, etc.
Object name is e-75-01738-efi2.jpg; (iii) An external file that holds a picture, illustration, etc.
Object name is e-75-01738-efi3.jpg; (iv) An external file that holds a picture, illustration, etc.
Object name is e-75-01738-efi4.jpg.

Database survey

A search in the Cambridge Structural Database (CSD, Version 5.4, May 2019 update; Groom et al., 2016) for the S-meth­yl(methyl­idene)thio­semicarbazidium cation yielded three results, viz. S-methyl-N-(pyrrolyl-2-methyl­ene)iso­thio­semi­car­bazidium iodide monohydrate (CSD refcode JIHZUV; Bourosh et al., 1990), 8-quinoline­aldehyde S-methyl­thio­semicarbazone hydro­chloride dihydrate (RUJXOK; Botoshansky et al., 2009) and ((E)-{2-[(E)-(4-hy­droxy­naphthalen-1-yl)methyl­idene]hydrazin-1-yl}(methyl­sulfan­yl)methyl­idene)aza­nium hydrogen sulfate monohydrate. The three-dimensional coordinates for the first structure are unavailable. A com­parison of the structures reveals that the cation in the RUJXOK structure is less planar than the cation in ESOTIR, the latter being more similar to the cation of the title com­pound. However, for structures RUJXOK and ESOTIR, the bond lengths and angles are similar to those of the title mol­ecular salt.

Synthesis and crystallization

An equimolar amount of thio­semicarbazide (10 mmol, 0.91 g) and 2,5-di­hydroxy­benzaldehyde (10 mmol, 1.38 g) were dissolved in a methanol–water solution in the presence of sulfuric acid. The mixture was then refluxed for 3 h. The solution was filtered and left to evaporate at room temperature. After slow evaporation, brown crystals suitable for X-ray diffraction analysis were obtained.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The hydrogen sulfate anion is disordered and had to be modelled as two conformations A and B, with relative occupancies of 0.501 (6) and 0.499 (6), respectively. H atoms were located in difference Fourier maps, but were subsequently included in calculated positions and treated as riding on their parent atoms with constrained thermal parameters: Uiso(H) = 1.5Ueq(C) and C—H = 0.98 Å for methyl H atoms, and Uiso(H) = 1.2Ueq(C,N) and C—H = 0.95 Å or N—H = 0.88 Å otherwise.

Table 2

Experimental details
Crystal data
Chemical formulaC9H12N3O2S·HSO4
Mr323.34
Crystal system, space groupMonoclinic, P21/n
Temperature (K)150
a, b, c (Å)4.9411 (8), 16.139 (2), 16.426 (3)
β (°)100.440 (7)
V)1288.2 (3)
Z4
Radiation typeMo Kα
μ (mm)0.44
Crystal size (mm)0.38 × 0.15 × 0.12
Data collection
DiffractometerBruker APEXII
Absorption correctionMulti-scan (SADABS; Bruker, 2015)
Tmin, Tmax0.838, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections7962, 2846, 2014
Rint0.045
(sin θ/λ)max)0.644
Refinement
R[F > 2σ(F)], wR(F), S0.050, 0.147, 1.03
No. of reflections2846
No. of parameters243
No. of restraints8
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å)0.36, −0.46

Computer programs: APEX2 (Bruker, 2015), SAINT (Bruker, 2015), SHELXT (Sheldrick, 2015a), SHELXL2018 (Sheldrick, 2015b), SXGRAPH (Farrugia, 1999), Mercury (Macrae et al., 2008) and CRYSCALC (T. Roisnel, local program).

Laboratoire de Chimie Inorganique et Environnement, Université de Tlemcen, BP 119, 13000 Tlemcen, Algeria,
Centre de Diffractometrie X, UMR 6226 CNRS, Unit Sciences Chimiques de Rennes, Universite de Rennes I, 263 Avenue du General Leclerc, 35042 Rennes, France,
Correspondence e-mail: moc.liamg@rahenamassuo
Received 2019 Sep 26; Accepted 2019 Oct 17.
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Abstract

The title mol­ecular salt, C9H12N3O2S·HSO4, was obtained through the protonation of the azomethine N atom in a sulfuric acid medium. The crystal com­prises two entities, a thio­semicarbazide cation and a hydrogen sulfate anion. The cation is essentially planar and is further stabilized by a strong intra­molecular O—H⋯N hydrogen bond. In the crystal, a three-dimensional network is established through O—H⋯O and N—H⋯O hydrogen bonds. A weak intermolecular C—H⋯O hydrogen bond is also observed. The hydrogen sulfate anion exhibits disorder over two sets of sites and was modelled with refined occupancies of 0.501 (6) and 0.499 (6).

Keywords: crystal structure, thio­semicarbazone, hydrogen bonding, organic salt
Abstract

Crystal structure: contains datablock(s) global. DOI: 10.1107/S2056989019014233/lh5926sup1.cif

Click here to view.(18K, cif)

CCDC references: 1960006, 1960006

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors are grateful for the support provided by the Algerian Ministry for Education and Research.

Acknowledgments

supplementary crystallographic information

Crystal data

C9H12N3O2S·HSO4F(000) = 672
Mr = 323.34Dx = 1.667 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 4.9411 (8) ÅCell parameters from 2859 reflections
b = 16.139 (2) Åθ = 2.5–27.0°
c = 16.426 (3) ŵ = 0.44 mm1
β = 100.440 (7)°T = 150 K
V = 1288.2 (3) Å3Prism, colourless
Z = 40.38 × 0.15 × 0.12 mm

Data collection

Bruker APEXII diffractometer2846 independent reflections
Radiation source: fine-focus sealed tube2014 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
CCD rotation images, thin slices scansθmax = 27.3°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2014)h = −6→4
Tmin = 0.838, Tmax = 0.948k = −19→20
7962 measured reflectionsl = −21→19

Refinement

Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F > 2σ(F)] = 0.050Hydrogen site location: mixed
wR(F) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ(Fo) + (0.086P)] where P = (Fo + 2Fc)/3
2846 reflections(Δ/σ)max < 0.001
243 parametersΔρmax = 0.36 e Å3
8 restraintsΔρmin = −0.46 e Å3

Special details

Geometry. 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.
Refinement. Refinement of F against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F, conventional R-factors R are based on F, with F set to zero for negative F. The threshold expression of F > 2sigma(F) 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 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 (Å)

xyzUiso*/UeqOcc. (<1)
S10.99180 (14)0.09724 (4)0.39012 (4)0.0247 (2)
C11.1843 (6)0.05832 (18)0.31564 (19)0.0283 (7)
H1A1.1037650.0791270.2605120.042*
H1B1.178644−0.0023770.3154740.042*
H1C1.3757610.0769560.3302290.042*
C21.0137 (5)0.20289 (18)0.37549 (16)0.0196 (6)
N31.1584 (4)0.23722 (15)0.32555 (15)0.0212 (5)
H3A1.163 (6)0.2922 (11)0.3217 (18)0.025*
H3B1.253 (5)0.2090 (17)0.2961 (16)0.025*
N40.8734 (5)0.25101 (15)0.41903 (15)0.0221 (5)
H40.897 (6)0.304 (2)0.4220 (19)0.027*
N50.7288 (4)0.21422 (15)0.47329 (14)0.0209 (5)
C60.6012 (5)0.26348 (17)0.51479 (17)0.0207 (6)
H60.6112340.3215650.5064370.025*
C70.4421 (5)0.23214 (17)0.57410 (16)0.0179 (6)
C80.4293 (5)0.14784 (17)0.59347 (17)0.0204 (6)
C90.2738 (5)0.12280 (18)0.65151 (18)0.0239 (6)
H90.2652690.0656630.6647100.029*
C100.1324 (5)0.17925 (17)0.69007 (17)0.0225 (6)
H100.0259880.1610370.7293730.027*
C110.1446 (5)0.26363 (17)0.67161 (17)0.0199 (6)
C120.2983 (5)0.28879 (17)0.61429 (16)0.0209 (6)
H120.3069230.3460850.6017280.025*
O130.5640 (4)0.08764 (12)0.55849 (13)0.0270 (5)
H130.648 (7)0.106 (2)0.527 (2)0.032*
O140.0054 (4)0.31741 (13)0.71335 (13)0.0279 (5)
H140.001 (6)0.366 (2)0.697 (2)0.034*
S2A0.8844 (12)0.5353 (4)0.6254 (4)0.0254 (10)0.501 (6)
O11A1.081 (3)0.4743 (10)0.6620 (9)0.031 (3)0.501 (6)
O12A0.810 (2)0.5938 (7)0.6848 (5)0.030 (2)0.501 (6)
O13A0.9688 (11)0.5797 (2)0.5572 (3)0.0297 (14)0.501 (6)
O14A0.6216 (9)0.4839 (3)0.5891 (3)0.0302 (13)0.501 (6)
H14A0.4762180.4813370.6086970.045*0.501 (6)
S2B0.9553 (12)0.5327 (5)0.6250 (5)0.0292 (12)0.499 (6)
O11B1.084 (4)0.4751 (12)0.6870 (8)0.038 (3)0.499 (6)
O12B0.767 (2)0.5891 (7)0.6534 (6)0.038 (2)0.499 (6)
O13B1.1639 (10)0.5733 (3)0.5857 (3)0.0294 (13)0.499 (6)
O14B0.7723 (10)0.4819 (4)0.5562 (3)0.0506 (17)0.499 (6)
H14B0.7938680.4637610.5098520.076*0.499 (6)

Atomic displacement parameters (Å)

U11U22U33U12U13U23
S10.0307 (4)0.0178 (4)0.0285 (4)−0.0005 (3)0.0136 (3)0.0018 (3)
C10.0313 (14)0.0220 (15)0.0354 (18)0.0012 (12)0.0162 (13)0.0003 (13)
C20.0205 (11)0.0207 (14)0.0172 (14)−0.0001 (11)0.0027 (11)−0.0014 (11)
N30.0252 (11)0.0175 (12)0.0236 (13)0.0011 (10)0.0114 (10)0.0049 (10)
N40.0285 (11)0.0178 (12)0.0228 (13)−0.0013 (10)0.0121 (10)0.0013 (10)
N50.0226 (10)0.0229 (12)0.0188 (12)−0.0018 (9)0.0079 (9)0.0010 (10)
C60.0230 (11)0.0178 (14)0.0220 (15)−0.0004 (11)0.0057 (11)0.0001 (11)
C70.0197 (11)0.0182 (13)0.0162 (14)−0.0007 (10)0.0040 (10)−0.0011 (11)
C80.0214 (11)0.0185 (14)0.0211 (15)−0.0003 (10)0.0035 (11)−0.0024 (11)
C90.0285 (13)0.0185 (14)0.0252 (15)−0.0032 (12)0.0063 (12)0.0006 (12)
C100.0249 (12)0.0238 (15)0.0201 (15)−0.0030 (11)0.0075 (11)0.0009 (12)
C110.0214 (11)0.0191 (14)0.0202 (14)0.0002 (11)0.0064 (11)−0.0040 (11)
C120.0244 (12)0.0172 (14)0.0213 (15)−0.0008 (11)0.0043 (11)0.0002 (11)
O130.0342 (11)0.0182 (10)0.0329 (13)0.0024 (9)0.0175 (9)−0.0009 (9)
O140.0363 (10)0.0186 (10)0.0336 (12)0.0014 (9)0.0186 (9)−0.0015 (9)
S2A0.038 (3)0.0164 (14)0.0231 (13)−0.0028 (16)0.0076 (16)0.0061 (9)
O11A0.028 (3)0.020 (3)0.043 (8)0.003 (3)0.007 (5)0.010 (5)
O12A0.040 (4)0.026 (3)0.026 (4)−0.010 (3)0.009 (3)−0.005 (3)
O13A0.050 (3)0.018 (2)0.026 (3)−0.004 (2)0.021 (2)0.0035 (18)
O14A0.031 (2)0.025 (2)0.038 (3)−0.0049 (18)0.016 (2)−0.0021 (19)
S2B0.037 (3)0.0182 (14)0.0338 (15)−0.0054 (16)0.0117 (17)−0.0075 (10)
O11B0.051 (4)0.030 (4)0.035 (7)−0.001 (3)0.014 (5)0.007 (5)
O12B0.038 (4)0.017 (3)0.062 (7)0.005 (3)0.021 (5)−0.011 (5)
O13B0.030 (3)0.025 (2)0.036 (3)0.0028 (19)0.014 (2)0.008 (2)
O14B0.042 (3)0.068 (4)0.044 (3)−0.018 (3)0.012 (3)−0.029 (3)

Geometric parameters (Å, º)

S1—C21.728 (3)C9—H90.9500
S1—C11.794 (3)C10—C111.399 (4)
C1—H1A0.9800C10—H100.9500
C1—H1B0.9800C11—O141.367 (3)
C1—H1C0.9800C11—C121.374 (3)
C2—N31.305 (3)C12—H120.9500
C2—N41.332 (3)O13—H130.78 (3)
N3—H3A0.890 (18)O14—H140.83 (4)
N3—H3B0.861 (17)S2A—O11A1.435 (8)
N4—N51.374 (3)S2A—O12A1.452 (7)
N4—H40.86 (3)S2A—O13A1.453 (6)
N5—C61.285 (3)S2A—O14A1.564 (8)
C6—C71.449 (3)O14A—H14A0.8399
C6—H60.9500S2B—O12B1.437 (7)
C7—C121.395 (4)S2B—O11B1.439 (8)
C7—C81.401 (4)S2B—O13B1.467 (6)
C8—O131.362 (3)S2B—O14B1.549 (9)
C8—C91.388 (4)O14B—H14B0.8401
C9—C101.371 (4)
C2—S1—C1101.32 (13)C10—C9—H9119.5
S1—C1—H1A109.5C8—C9—H9119.5
S1—C1—H1B109.5C9—C10—C11120.1 (2)
H1A—C1—H1B109.5C9—C10—H10120.0
S1—C1—H1C109.5C11—C10—H10120.0
H1A—C1—H1C109.5O14—C11—C12123.2 (3)
H1B—C1—H1C109.5O14—C11—C10117.6 (2)
N3—C2—N4119.2 (3)C12—C11—C10119.2 (2)
N3—C2—S1124.2 (2)C11—C12—C7121.5 (3)
N4—C2—S1116.7 (2)C11—C12—H12119.2
C2—N3—H3A119.5 (19)C7—C12—H12119.2
C2—N3—H3B123 (2)C8—O13—H13112 (2)
H3A—N3—H3B118 (3)C11—O14—H14115 (2)
C2—N4—N5118.6 (2)O11A—S2A—O12A113.5 (9)
C2—N4—H4122 (2)O11A—S2A—O13A113.2 (7)
N5—N4—H4118 (2)O12A—S2A—O13A109.8 (7)
C6—N5—N4116.1 (2)O11A—S2A—O14A104.4 (10)
N5—C6—C7121.3 (3)O12A—S2A—O14A107.9 (5)
N5—C6—H6119.4O13A—S2A—O14A107.6 (5)
C7—C6—H6119.4S2A—O14A—H14A126.1
C12—C7—C8118.7 (2)O12B—S2B—O11B114.1 (9)
C12—C7—C6118.3 (2)O12B—S2B—O13B114.0 (7)
C8—C7—C6123.0 (2)O11B—S2B—O13B110.1 (9)
O13—C8—C9117.1 (2)O12B—S2B—O14B104.2 (6)
O13—C8—C7123.4 (2)O11B—S2B—O14B107.4 (11)
C9—C8—C7119.5 (2)O13B—S2B—O14B106.2 (5)
C10—C9—C8121.0 (3)S2B—O14B—H14B133.8
C1—S1—C2—N3−4.6 (3)C6—C7—C8—C9179.5 (2)
C1—S1—C2—N4175.8 (2)O13—C8—C9—C10179.7 (2)
N3—C2—N4—N5−178.0 (2)C7—C8—C9—C100.1 (4)
S1—C2—N4—N51.6 (3)C8—C9—C10—C11−0.4 (4)
C2—N4—N5—C6178.8 (2)C9—C10—C11—O14−178.4 (2)
N4—N5—C6—C7−179.8 (2)C9—C10—C11—C120.3 (4)
N5—C6—C7—C12−177.1 (2)O14—C11—C12—C7178.7 (2)
N5—C6—C7—C83.7 (4)C10—C11—C12—C70.1 (4)
C12—C7—C8—O13−179.3 (2)C8—C7—C12—C11−0.4 (4)
C6—C7—C8—O13−0.1 (4)C6—C7—C12—C11−179.6 (2)
C12—C7—C8—C90.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···AD—HH···AD···AD—H···A
C10—H10···O12Ai0.952.603.541 (10)170
N3—H3A···O12Aii0.89 (2)1.85 (2)2.738 (12)178 (3)
N3—H3A···O12Bii0.89 (2)1.98 (2)2.841 (11)163 (3)
N3—H3B···O14iii0.86 (2)2.05 (2)2.874 (3)160 (3)
N4—H4···O13Aii0.86 (3)2.00 (3)2.849 (5)167 (3)
N4—H4···O13Bii0.86 (3)2.00 (3)2.841 (5)164 (3)
O13—H13···N50.78 (3)2.03 (3)2.685 (3)142 (3)
O14—H14···O11Aiv0.83 (4)1.90 (4)2.716 (16)167 (3)
O14—H14···O11Biv0.83 (4)1.82 (4)2.62 (2)162 (3)
O14A—H14A···O11Aiv0.842.283.123 (17)180
O14B—H14B···S2Bii0.842.733.490 (9)152
O14B—H14B···O13Bii0.841.732.567 (7)180

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+2, −y+1, −z+1; (iii) x+3/2, −y+1/2, z−1/2; (iv) x−1, y, z.

supplementary crystallographic information
Collaboration tool especially designed for Life Science professionals.Drag-and-drop any entity to your messages.