research communications
Synthesis, tert-butyl N-acetylcarbamate
and Hirshfeld surface analysis ofaUnité de Chimie Moléculaire et Environnement, Département de Chimie, FST, UNA, Nouakchott, Mauritania, bDépartement des Sciences Exactes, Ecole Normale Supérieure de Nouakchott, Nouakchott, Mauritania, cAgence Nationale de Recherches Géologiques et du Patrimoine Minier (ANARPAM), Nouakchott, Mauritania, dLaboratoire CRM2, CNRS, Institut Jean Barriol, Université de, Lorraine, 54000, Nancy, France, and eDépartement de Chimie, Faculté des Sciences et Techniques, Université Cheik Anta Diop, Dakar, Senegal
*Correspondence e-mail: mlgayeastou@yahoo.fr
This article reports a practical synthesis of tert-butyl acetylcarbamate, C7H13NO3, from N-Boc-thioacetamide and the study of its The reaction proceeds in the presence of natural phosphate as a catalyst, with excellent yield, simple workup and benign environment. The was refined using a transferred multipolar atom model. In the crystal, symmetrical pairs of strong N—H⋯O hydrogen bonds connect the molecules into dimers with an R22(8) ring motif. The interactions between neighbouring dimers are mostly van der Waals, between hydrophobic methyl groups. Hirshfeld surface analysis shows the major contributions to the crystal packing are from H⋯H (42.6%) and O⋯H (26.7%) contacts.
Keywords: X-ray crystal structure; tert-butyl acetylcarbamate; natural phosphate; Mauritanian phosphate deposit.
CCDC reference: 2209649
1. Chemical context
et al., 2002) and in medicinal chemistry, where many derivatives are specifically designed to make drug–target interactions through their carbamate moiety (Ghosh & Brindisi, 2015). Here we report the of tert-butyl-acetylcarbamate, C7H13NO3 (I), which we obtained while attempting to synthesize polyfunctional (which are useful in synthetic fields, especially as templates for the development of various novel heterocycles) using on natural phosphates (NP) – readily available, stable, easy to handle and regenerate, non-toxic and inexpensive catalysts with both basic and acidic active sites (Sebti et al., 1994, 1996).
are widely used as agrochemicals, in the polymer industry, in peptide synthesis (DibenedettoWe followed the procedure described by Lee et al. (1998), but using natural phosphate (NP) as a catalyst instead of Lewis acids such as ZnCl2, Et3O+BF4− and FeCl2. The synthesis was carried out by blending N-(t-Boc)thioacetamide with various aminoesters, in the presence of NEt3 and NP. The reaction yielded (I) instead of the desired amidine, i.e. the sulfur atom was substituted by oxygen. In the absence of NP, no product was obtained and the starting materials were recovered.
2. Structural commentary
The title compound, C7H13NO3, (Fig. 1) crystallizes in the P21/n with one molecule per The skeleton of the molecule is nearly planar if the C3 and C4 atoms are excluded, the root-mean-square deviation from the mean plane being 0.070 Å. The C3H3 and C4H3 methyl groups, located on either side of the mean plane, generate two weak intramolecular hydrogen bonds with the carbonyl O2 atom located in the plane [C3—H3C⋯O2 and C4—H4A⋯O2, d(H⋯O)= 2.49 and 2.48 Å, respectively; Table 1].
3. Supramolecular features
In the crystal, a centrosymmetric dimer of molecules is held together by two N—H⋯O=C hydrogen bonds, N1—H1⋯O3 and its symmetry equivalent [d(H⋯O) = 1.92 (1) Å, Table 1], which represent the strongest interactions in the packing and create an inversion-symmetric supramolecular motif of graph-set (8) (Fig. 2). Fig. 3 shows the packing of these dimers. If we consider the Hirshfeld surface around the dimer as a whole, this surface is constituted mainly by hydrophobic (C and H-c) atoms (81%) and oxygen atoms (13%). The interactions between neighbouring dimers are mostly hydrophobic: H-c⋯H-c between methyl groups (43%) and C⋯H-c between carbonyl and methyl groups (21%). Weak C—H⋯O hydrogen bonds also occur between dimers (23%). The of the methyl groups causes an offset of the molecules of consecutive dimers, so that no strong hydrogen bond is observed between the dimers. Consequently, the crystal appears to be stabilized by strong hydrogen bonding within the dimers and without.
4. Hirshfeld analysis
MoProViewer (Jelsch et al., 2005) was used to further investigate and visualize the intermolecular interactions in the crystal. The Hirshfeld surface was computed from the model after multipolar but using electron density from the spherical-neutral atom model. The 2D fingerprint plots (Fig. 4) were generated with Crystal Explorer (Spackman et al., 2021). The most significant contributions for the contacts in the crystal packing (Table 2) are from H⋯H (46.2%), O⋯H/H⋯O (26.7%) and C⋯H/H⋯C contacts (18.7%), whereas only 2.8% are from N⋯H/H⋯N contacts. In the fingerprint plots (Fig. 4), the two reciprocal spikes at a short distance correspond to the O⋯H—N/N—H⋯O contacts, i.e. strong hydrogen bonds. The H⋯H contacts show also a small spike on the diagonal line, the shortest distances being 2.447 Å between H2B and H7A(x + 1, y − 1, z) (Fig. 5a). The intermolecular interactions were further evaluated by computing the enrichment ratios (E, see Table 2) in order to highlight which contacts are over-represented and are likely to represent energetically strong interactions and be the driving force in crystal formation (Jelsch et al., 2014). The enrichment values are obtained as the ratio between the shares of actual contacts Cxy and the random (equiprobable) contacts Rxy, the latter calculated as if all types of contacts had the same propensity to occur and are obtained by probability products (Rxy = Sx·Sy). The H-c⋯H-c hydrophobic contacts are the most abundant on the Hirshfeld surface but have a unitary enrichment ratio. The O⋯H-c and C⋯H-c weak hydrogen bonds are the next most abundant interactions and are slightly enriched (E = 1.04 and 1.12, respectively). While the strong O⋯H-n hydrogen bonds in the fourth position represent only 5.9% of the contact surface, they are the most enriched at E = 3.41. The H-c⋯N contacts are over-represented with E = 1.46 as the nitrogen atom interacts mostly with methyl groups on both sides of the sp2 plane.
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The Hirshfeld surface was partitioned into (H-c, C) and (H-n, O, N) atoms' shares in order to analyse the contacts in terms of hydrophobic and hydrophilic interactions. Overall, hydrophobic atoms (C and H-c) comprise 77.5% of the surface, but the hydrophobic contacts between these atoms (61.8%) are not significantly enriched at E = 1.03. Contacts between hydrophilic atoms (22.5% of the surface), mostly in the form of strong hydrogen bonds, are enriched to 6.7% (E = 1.32) while cross-interactions (between hydrophobic and hydrophilic atoms) are under-represented (31.6%, E = 0.90).
The electrostatic potential was computed on the Hirshfeld and van der Waals surfaces of the molecule (Fig. 5). The two surfaces show similar potential values which are both in the −0.12 to +0.12 e Å−1 range. The regions around the three oxygen atoms are electronegative while the NH group displays positive potential on the surface, followed by the methyl groups which are moderately electropositive.
5. Database survey
The Cambridge Structural Database (Version 5.43, November 2021; Groom et al., 2016) was surveyed using ConQuest (version 2020.2.0; Bruno et al., 2002). The eight-membered supramolecular motif, with a double N—H⋯O=C hydrogen bond between two amide groups, is quite common, being encountered in 10,336 crystal structures. The amide-ester fragment, encountered in 35 structures, exists in three different near-planar conformations (Fig. 6). Conformation (a) with the syn disposition of C=O bonds appears in 23 structures, including the nearest reported analogue of (I), 1,1-dimethylethyl-N-propanoylcarbamate (II) (Brodesser et al., 2003). Two different anti conformations, (b) and (c), are adopted by nine and three compounds, respectively. Molecule (I) adopts the anti conformation (b). Compound (I) is the homologue of (II).
6. Synthesis and crystallization
Materials and physical methods. All reagents were purchased from Sigma-Aldrich. Reaction progress was monitored by (TLC) on silica-gel plates (Fluka Kieselgel 60 F254). Flash purifications were performed on Interchim Puriflash (Puriflash columns 50 µ). was performed on a PANalytical AxiosmAX spectrometer.
Preparation of the catalyst. The NP used in this work comes from the Bofal phosphate deposit in Mauritania. Before being used in catalysis, it underwent quartering treatment, particle-size separation, aqueous dissolution, filtration and evaporation of water, at 1173 K for 1h and grinding. The fraction of 60–100 µm grain size was used. The nominal chemical compositions of this phosphate were given by (XRF) analysis. The total amount of the natural inorganic components was 90.86% (Table 3). The rest was mainly organic matter, as indicated by the weight loss on combustion, which amounted to 10.43%.
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Preparation of tert-butyl acetylcarbamate (I). It should be noted that compound (I) was prepared in our attempt to synthesize polyfunctional which are useful in synthetic fields, especially as a template for the development of various new heterocycles. In the preparation, we used the same operating conditions as Lee et al. (1998), substituting NP as the catalyst for a To a solution of N-(t-Boc)thioacetamide (87.6 mg; 0.5 mmol), the hydrochloride salt of an amino ester (0.5 mmol) and triethylamine (1.65 mmol) in a dry solvent (10 mL), NP (87.6 mg) was added with stirring. The reaction was stirred for 30 min at room temperature. The mixture was filtered through a pad of celite. The residue was purified by Interchim Puriflash (Puriflash columns 50 µ) using a cyclohexane/ethyl acetate system, to yield crystalline (I) in a very high yield (≥ 95%). We have tested this reaction with various solvents (THF, CH3CN and DMF) and hydrochlorides of different amino viz. glycine ethyl ester, L-valine methyl ester, L-alanine ethyl ester and L-phenylalanine methyl ester. N-(Boc)thioacetamide was prepared as described in the literature (Lee et al., 1998).
7. Refinement
Crystal data, data collection and structure . A least-squares based on |F|2 of all reflections, was carried out with the program MoPro (Jelsch et al., 2005) using the ELMAM2 electron-density database (Domagała et al., 2012). In this approach, scale factors, atomic positions and displacement parameters for all atoms were varied, but a multipolar charged-atom model was applied until convergence. The H—X distances were constrained to the standard values in neutron diffraction studies (Allen & Bruno, 2010). The anisotropic displacement parameters of hydrogen atoms were constrained to the values obtained from the SHADE3 server (Madsen & Hoser, 2014). Two subsets of the molecule (O-t-butyl moiety and the rest of the molecule) were used as input to the SHADE3 program to obtain better estimations of the Uani(H) displacement parameters. The use of a transferred multipolar atom model allowed the reduction of R(F) to 4.6% and wR2(F2) to 7.2%, compared to 6.1% and 11.8%, respectively, for the neutral-spherical atom model, as refined in MoPro. The r.m.s. residual electron density was likewise reduced from 0.042 to 0.034 e Å−3.
details are summarized in Table 4Supporting information
CCDC reference: 2209649
https://doi.org/10.1107/S2056989022009483/zv2015sup1.cif
contains datablock I. DOI:The hkl file is provided as suppemental material. DOI: https://doi.org/10.1107/S2056989022009483/zv2015sup3.txt
Supporting information file. DOI: https://doi.org/10.1107/S2056989022009483/zv2015Isup3.cml
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: MoPro (Jelsch et al., 2005); molecular graphics: MoPro (Jelsch et al., 2005); software used to prepare material for publication: MoPro (Jelsch et al., 2005).C7H13NO3 | F(000) = 344 |
Mr = 159.18 | Dx = 1.168 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4200 reflections |
a = 6.0404 (6) Å | θ = 2.4–28.6° |
b = 8.6114 (7) Å | µ = 0.09 mm−1 |
c = 17.6110 (17) Å | T = 293 K |
β = 98.771 (9)° | Block, colorless |
V = 905.35 (15) Å3 | 0.15 × 0.1 × 0.08 mm |
Z = 4 |
Bruker Kappa CCD diffractometer | 1627 reflections with I > 2 σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 27.5°, θmin = 2.6° |
CCD scans | h = −7→7 |
2405 measured reflections | k = 0→11 |
2059 independent reflections | l = 0→22 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Only H-atom coordinates refined |
wR(F2) = 0.072 | w = 1/[4.4*σ2(Fo2)] |
S = 1.00 | (Δ/σ)max = 0.002 |
2059 reflections | Δρmax = 0.16 e Å−3 |
139 parameters | Δρmin = −0.17 e Å−3 |
31 restraints | Extinction correction: Isotropic Gaussian |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.51132 |
Refinement. Refinement of F2 against reflections. The threshold expression of F2 > 2sigma(F2) is used for calculating R-factors(gt) 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.38211 (11) | 0.355396 (15) | 0.40123 (4) | 0.05484 (14) | |
O2 | 0.63464 (12) | 0.29985 (8) | 0.32233 (4) | 0.06801 (17) | |
O3 | 0.73388 (12) | −0.08048 (8) | 0.46784 (4) | 0.06574 (16) | |
N1 | 0.57479 (13) | 0.14069 (8) | 0.42246 (5) | 0.05046 (16) | |
H1 | 0.474 (2) | 0.1271 (16) | 0.4629 (7) | 0.08754 | |
C5 | 0.54053 (15) | 0.27070 (10) | 0.37571 (5) | 0.04754 (17) | |
C6 | 0.73373 (15) | 0.02549 (11) | 0.42216 (6) | 0.05121 (18) | |
C1 | 0.30097 (15) | 0.50254 (10) | 0.36327 (6) | 0.05446 (18) | |
C7 | 0.89889 (19) | 0.03248 (14) | 0.36770 (7) | 0.0716 (3) | |
H7A | 1.0210 (16) | −0.0607 (14) | 0.3829 (8) | 0.10454 | |
H7B | 0.9899 (18) | 0.1427 (14) | 0.3755 (9) | 0.11089 | |
H7C | 0.818 (2) | 0.0353 (17) | 0.3076 (6) | 0.11503 | |
C4 | 0.18467 (19) | 0.46831 (14) | 0.28329 (7) | 0.0740 (3) | |
H4A | 0.3039 (17) | 0.4270 (16) | 0.2468 (6) | 0.10880 | |
H4B | 0.106 (2) | 0.5761 (14) | 0.2597 (8) | 0.11611 | |
H4C | 0.0505 (16) | 0.3836 (15) | 0.2852 (8) | 0.11411 | |
C3 | 0.4904 (2) | 0.61607 (13) | 0.36559 (8) | 0.0758 (2) | |
H3A | 0.578 (2) | 0.6274 (16) | 0.4245 (8) | 0.11708 | |
H3B | 0.419 (2) | 0.7310 (12) | 0.3505 (9) | 0.12094 | |
H3C | 0.6142 (17) | 0.5881 (15) | 0.3283 (7) | 0.10779 | |
C2 | 0.1345 (2) | 0.55587 (15) | 0.41419 (8) | 0.0822 (3) | |
H2A | 0.0073 (16) | 0.4648 (14) | 0.4127 (9) | 0.11714 | |
H2B | 0.054 (2) | 0.6620 (14) | 0.3891 (8) | 0.12347 | |
H2C | 0.232 (2) | 0.5828 (17) | 0.4703 (7) | 0.12492 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0660 (4) | 0.0489 (4) | 0.0515 (4) | 0.0085 (3) | 0.0150 (3) | 0.0127 (3) |
O2 | 0.0786 (5) | 0.0669 (5) | 0.0644 (5) | 0.0061 (4) | 0.0300 (4) | 0.0184 (3) |
O3 | 0.0745 (5) | 0.0484 (4) | 0.0771 (5) | 0.0077 (3) | 0.0204 (4) | 0.0162 (3) |
N1 | 0.0599 (5) | 0.0439 (4) | 0.0495 (5) | 0.0021 (3) | 0.0144 (3) | 0.0091 (3) |
H1 | 0.09872 | 0.08344 | 0.09180 | 0.02741 | 0.05087 | 0.03885 |
C5 | 0.0539 (5) | 0.0441 (5) | 0.0456 (5) | −0.0003 (4) | 0.0107 (4) | 0.0056 (4) |
C6 | 0.0573 (5) | 0.0430 (5) | 0.0533 (5) | −0.0001 (4) | 0.0083 (4) | 0.0024 (4) |
C1 | 0.0592 (5) | 0.0460 (5) | 0.0551 (5) | 0.0050 (4) | −0.0011 (4) | 0.0103 (4) |
C7 | 0.0720 (7) | 0.0747 (7) | 0.0731 (7) | 0.0168 (6) | 0.0274 (6) | 0.0133 (6) |
H7A | 0.09887 | 0.10412 | 0.11797 | 0.04100 | 0.04001 | 0.02395 |
H7B | 0.08822 | 0.09468 | 0.16018 | −0.00028 | 0.05229 | 0.03275 |
H7C | 0.14423 | 0.13621 | 0.06953 | 0.04903 | 0.03193 | 0.00590 |
C4 | 0.0757 (7) | 0.0794 (8) | 0.0597 (7) | −0.0079 (6) | −0.0129 (5) | 0.0126 (6) |
H4A | 0.12776 | 0.13382 | 0.06263 | 0.00285 | 0.00747 | 0.00354 |
H4B | 0.11933 | 0.11272 | 0.10174 | 0.01287 | −0.02973 | 0.03707 |
H4C | 0.09893 | 0.11674 | 0.11538 | −0.03490 | −0.01984 | 0.00269 |
C3 | 0.0723 (7) | 0.0514 (6) | 0.0968 (9) | −0.0083 (5) | −0.0096 (6) | 0.0110 (6) |
H3A | 0.11467 | 0.09511 | 0.12396 | −0.01659 | −0.03780 | −0.00724 |
H3B | 0.11702 | 0.05611 | 0.17940 | −0.00332 | −0.01031 | 0.02819 |
H3C | 0.08755 | 0.09430 | 0.14362 | −0.01523 | 0.02433 | 0.02842 |
C2 | 0.0844 (8) | 0.0751 (8) | 0.0889 (9) | 0.0249 (6) | 0.0193 (6) | 0.0046 (7) |
H2A | 0.09735 | 0.11323 | 0.15160 | 0.01562 | 0.05342 | 0.02003 |
H2B | 0.12561 | 0.09416 | 0.15181 | 0.05340 | 0.02495 | 0.01964 |
H2C | 0.15392 | 0.13217 | 0.08898 | 0.04922 | 0.01950 | −0.01800 |
O1—C5 | 1.3344 (11) | C7—H7A | 1.0950 |
O1—C1 | 1.4808 (9) | C7—H7B | 1.0950 |
O2—C5 | 1.1970 (11) | C4—H4C | 1.0950 |
O3—C6 | 1.2164 (11) | C4—H4A | 1.0950 |
N1—C5 | 1.3864 (12) | C4—H4B | 1.0950 |
N1—C6 | 1.3811 (12) | C3—H3C | 1.0950 |
N1—H1 | 1.013 (8) | C3—H3B | 1.0950 |
C6—C7 | 1.4868 (15) | C3—H3A | 1.0950 |
C1—C3 | 1.5009 (14) | C2—H2C | 1.0950 |
C1—C4 | 1.5042 (15) | C2—H2B | 1.0950 |
C1—C2 | 1.5170 (16) | C2—H2A | 1.0950 |
C7—H7C | 1.0950 | ||
C5—O1—C1 | 121.38 (6) | H7C—C7—H7B | 104 (1) |
C5—N1—C6 | 128.22 (7) | H7A—C7—H7B | 107.3 (8) |
C5—N1—H1 | 117.3 (7) | C1—C4—H4C | 110.1 (7) |
C6—N1—H1 | 114.4 (7) | C1—C4—H4A | 111.0 (6) |
O1—C5—O2 | 126.91 (8) | C1—C4—H4B | 107.6 (6) |
O1—C5—N1 | 106.93 (7) | H4C—C4—H4A | 111 (1) |
O2—C5—N1 | 126.15 (7) | H4C—C4—H4B | 107.3 (10) |
O3—C6—N1 | 117.82 (7) | H4A—C4—H4B | 110 (1) |
O3—C6—C7 | 121.61 (8) | C1—C3—H3C | 115.4 (7) |
N1—C6—C7 | 120.57 (8) | C1—C3—H3B | 108.2 (6) |
O1—C1—C3 | 110.28 (7) | C1—C3—H3A | 109.8 (7) |
O1—C1—C4 | 109.28 (7) | H3C—C3—H3B | 109 (1) |
O1—C1—C2 | 101.29 (7) | H3C—C3—H3A | 108.3 (10) |
C3—C1—C4 | 113.48 (8) | H3B—C3—H3A | 105 (1) |
C3—C1—C2 | 110.99 (9) | C1—C2—H2C | 106.5 (7) |
C4—C1—C2 | 110.85 (9) | C1—C2—H2B | 107.8 (8) |
C6—C7—H7C | 112.4 (7) | C1—C2—H2A | 107.1 (7) |
C6—C7—H7A | 107.8 (6) | H2C—C2—H2B | 109.3 (10) |
C6—C7—H7B | 109.1 (7) | H2C—C2—H2A | 117 (1) |
H7C—C7—H7A | 115.8 (9) | H2B—C2—H2A | 108.8 (10) |
O1—C5—N1—C6 | −174.66 (12) | H1—N1—C6—C7 | −178 (1) |
O1—C5—N1—H1 | 4 (1) | C5—O1—C1—C3 | −60.18 (11) |
O1—C1—C3—H3C | 71.1 (8) | C5—O1—C1—C4 | 65.21 (11) |
O1—C1—C3—H3B | −166.1 (9) | C5—O1—C1—C2 | −177.77 (12) |
O1—C1—C3—H3A | −51.6 (9) | C5—N1—C6—C7 | 1.01 (14) |
O1—C1—C4—H4C | 55.5 (7) | C4—C1—C3—H3C | −51.9 (7) |
O1—C1—C4—H4A | −67.8 (7) | C4—C1—C3—H3B | 70.9 (7) |
O1—C1—C4—H4B | 172.1 (9) | C4—C1—C3—H3A | −174.6 (9) |
O1—C1—C2—H2C | 66.4 (7) | C4—C1—C2—H2C | −177.8 (9) |
O1—C1—C2—H2B | −176.4 (7) | C4—C1—C2—H2B | −60.5 (7) |
O1—C1—C2—H2A | −59.4 (7) | C4—C1—C2—H2A | 56.4 (8) |
O2—C5—O1—C1 | 0.45 (12) | H4A—C4—C1—C3 | 56 (1) |
O2—C5—N1—C6 | 5.90 (14) | H4A—C4—C1—C2 | −179 (1) |
O2—C5—N1—H1 | −175 (1) | H4B—C4—C1—C3 | −64 (1) |
O3—C6—N1—C5 | −179.23 (13) | H4B—C4—C1—C2 | 61 (1) |
O3—C6—N1—H1 | 2 (1) | H4C—C4—C1—C3 | 179 (1) |
O3—C6—C7—H7C | 121.4 (9) | H4C—C4—C1—C2 | −55 (1) |
O3—C6—C7—H7A | −7.4 (8) | C3—C1—C2—H2C | −50.7 (7) |
O3—C6—C7—H7B | −123.6 (8) | C3—C1—C2—H2B | 66.5 (8) |
N1—C5—O1—C1 | −178.99 (12) | C3—C1—C2—H2A | −176.5 (8) |
N1—C6—C7—H7C | −58.8 (8) | H3A—C3—C1—C2 | 60 (1) |
N1—C6—C7—H7A | 172.4 (8) | H3B—C3—C1—C2 | −55 (1) |
N1—C6—C7—H7B | 56.1 (8) | H3C—C3—C1—C2 | −177 (1) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O2 | 1.10 | 2.48 | 3.0651 (14) | 112 |
C3—H3C···O2 | 1.10 | 2.49 | 2.9928 (15) | 107 |
N1—H1···O3i | 1.01 (1) | 1.92 (1) | 2.9285 (11) | 173 (1) |
Symmetry code: (i) −x+1, −y, −z+1. |
H-c and H-n signify hydrogen atoms bound to C (hydrophobic) and N (hydrophilic), respectively. Reciprocal contacts (X···Y and Y···X) are merged. The most prevalent and enriched contacts are highlighted in bold. |
Atom | H-n | N | O | H-c | C |
Sx (%) | 5.5 | 1.5 | 15.5 | 64.0 | 13.5 |
Cxy (%) (Exy) | |||||
H-n | 0.4 (1.39) | ||||
N | 0 (0) | 0 (0) | |||
O | 5.9 (3.41) | 0 (0) | 0.4 (0.16) | ||
H-c | 4.2 (0.59) | 2.8 (1.46) | 20.8 (1.04) | 41.6 (0.99) | |
C | 0.2 (0.13) | 0.1 (0.41) | 3.4 (0.86) | 18.5 (1.12) | 1.6 (1.00) |
SiO2 | TiO2 | Al2O3 | Fe2O3 | MgO | CaO | Na2O | K2O | MnO | P2O5 | SO3 |
14.17 | 0.058 | 17.51 | 0.530 | 0.245 | 31.66 | 0.319 | 0.113 | 0.016 | 26.18 | 0.060 |
Funding information
The authors are grateful to Ministère de l'Enseignement Supéreur et de la Recherche Scientifique de la République Islamique de Mauritanie and the Service de Coopération et d'Action Culturelle (SCAC) de l'Ambassade de France en Mauritanie for financial support.
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