metal-organic compounds
Sodium 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate
aDepartment of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, bDepartment of Chemistry, College of Science and Humanities, Shaqra University, Duwadimi, Saudi Arabia, cApplied Organic Chemistry Department, National Research Centre, Dokki, Giza, Egypt, dNational Center for Petrochemicals Technology, King Abdulaziz City for Science and Technology, PO Box 6086, Riyadh 11442, Saudi Arabia, eDepartment of Chemistry, College of Science, Al-Nahrain University, Baghdad 64021, Iraq, and fSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
*Correspondence e-mail: gelhiti@ksu.edu.sa, kariukib@cardiff.ac.uk
In the title molecular salt, Na+·C10H7ClN3O2−, the dihedral angles between the planes of adjacent chlorophenyl, methyltriazole and carboxylate groups of the anion are 50.2 (1) and 9.0 (3)°, respectively. The shortest distance between sodium cations is 4.0595 (9) Å. The sodium cation is coordinated by two N atoms and three O atoms, generating layers of ions lying parallel to the bc plane.
Keywords: crystal structure; 1,2,3-triazole; carboxylate.
CCDC reference: 1860692
Structure description
1,2,3-Triazole-4-carboxylic acids are important precursors for various biologically active compounds that act as xanthine oxidase inhibitors (Zhang et al., 2017; Ojha et al., 2017) and antibacterial (Maji & Haldar, 2017) and antitubercular (Kamal et al., 2013) agents. As part of our studies in this area, we now describe the synthesis and structure of the title salt.
The + cation and a C10H7ClN3O2− anion (Fig. 1). The anion consists of chlorophenyl, methyltriazolyl and carboxylate groups, and the twist angles between the planes through adjacent groups are 50.2 (1) and 9.0 (3)°, respectively. The shortest distance between sodium cations is 4.0595 (9) Å and each cation is coordinated by two N atoms, with an average Na—N distance of 2.5654 (6) Å, and by three O atoms, with an average Na⋯O distance of 2.37 (4) Å. The resulting is a very distorted trigonal bipyramid with one N atom and one O atom in the axial sites. The extended structure generates layers of ions parallel to the bc plane (Fig. 2). A short C—H⋯N contact is also observed (Table 1).
comprises a NaSynthesis and crystallization
The title compound was synthesized from the reaction of 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid and sodium hydroxide (10%) in ethanol under reflux for 4 h. The crude product obtained after work-up was recrystallized from dimethylformamide solution to give colourless blocks.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1860692
https://doi.org/10.1107/S2414314618011276/hb4252sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618011276/hb4252Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314618011276/hb4252Isup3.cml
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell
CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and WinGX (Farrugia, 2012); software used to prepare material for publication: ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).Na+·C10H7ClN3O2− | F(000) = 528 |
Mr = 259.63 | Dx = 1.582 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.6462 (8) Å | Cell parameters from 2649 reflections |
b = 6.3754 (4) Å | θ = 3.5–29.2° |
c = 14.7003 (9) Å | µ = 0.38 mm−1 |
β = 92.711 (7)° | T = 293 K |
V = 1090.26 (12) Å3 | Block, colourless |
Z = 4 | 0.42 × 0.16 × 0.07 mm |
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | 1875 reflections with I > 2σ(I) |
ω scans | Rint = 0.030 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015) | θmax = 29.7°, θmin = 3.2° |
Tmin = 0.467, Tmax = 1.000 | h = −14→15 |
8333 measured reflections | k = −8→8 |
2665 independent reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0446P)2 + 0.2829P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2665 reflections | Δρmax = 0.25 e Å−3 |
155 parameters | Δρmin = −0.40 e Å−3 |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.08988 (16) | 0.5137 (3) | 0.64261 (13) | 0.0306 (4) | |
C2 | 0.12619 (15) | 0.6087 (3) | 0.55520 (12) | 0.0277 (4) | |
C3 | 0.19398 (17) | 0.5260 (3) | 0.48997 (13) | 0.0304 (4) | |
C4 | 0.2601 (2) | 0.3285 (3) | 0.48670 (17) | 0.0597 (8) | |
H4A | 0.209664 | 0.215967 | 0.467891 | 0.090* | |
H4B | 0.294116 | 0.298547 | 0.546045 | 0.090* | |
H4C | 0.319562 | 0.342836 | 0.444051 | 0.090* | |
C5 | 0.25655 (16) | 0.6837 (3) | 0.34347 (13) | 0.0302 (4) | |
C6 | 0.24624 (18) | 0.5191 (3) | 0.28293 (14) | 0.0378 (5) | |
H6 | 0.201366 | 0.403343 | 0.296042 | 0.045* | |
C7 | 0.30294 (19) | 0.5273 (4) | 0.20265 (14) | 0.0448 (6) | |
H7 | 0.297119 | 0.416527 | 0.161513 | 0.054* | |
C8 | 0.36800 (18) | 0.7002 (4) | 0.18405 (14) | 0.0421 (5) | |
C9 | 0.3785 (2) | 0.8660 (4) | 0.24377 (15) | 0.0481 (6) | |
H9 | 0.422407 | 0.982653 | 0.230039 | 0.058* | |
C10 | 0.32262 (19) | 0.8562 (3) | 0.32453 (15) | 0.0429 (5) | |
H10 | 0.329600 | 0.965933 | 0.366091 | 0.052* | |
N1 | 0.09199 (14) | 0.8041 (2) | 0.52889 (11) | 0.0337 (4) | |
N2 | 0.13405 (15) | 0.8474 (2) | 0.45008 (11) | 0.0355 (4) | |
N3 | 0.19683 (13) | 0.6783 (2) | 0.42611 (10) | 0.0292 (4) | |
O1 | 0.11449 (14) | 0.3261 (2) | 0.65583 (10) | 0.0469 (4) | |
O2 | 0.03699 (12) | 0.6316 (2) | 0.69418 (9) | 0.0406 (4) | |
Cl1 | 0.43802 (6) | 0.70889 (13) | 0.08201 (4) | 0.0687 (3) | |
Na1 | −0.01461 (7) | 0.49886 (11) | 0.83416 (5) | 0.0360 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0339 (11) | 0.0277 (10) | 0.0310 (10) | −0.0038 (8) | 0.0085 (9) | 0.0010 (8) |
C2 | 0.0327 (10) | 0.0239 (9) | 0.0269 (9) | −0.0009 (7) | 0.0067 (8) | −0.0022 (7) |
C3 | 0.0376 (11) | 0.0241 (9) | 0.0303 (10) | −0.0014 (7) | 0.0100 (9) | 0.0016 (8) |
C4 | 0.0875 (19) | 0.0378 (12) | 0.0569 (15) | 0.0222 (12) | 0.0378 (14) | 0.0114 (11) |
C5 | 0.0345 (10) | 0.0332 (9) | 0.0234 (9) | 0.0004 (8) | 0.0067 (8) | −0.0006 (8) |
C6 | 0.0419 (12) | 0.0384 (11) | 0.0336 (11) | −0.0062 (9) | 0.0081 (9) | −0.0057 (9) |
C7 | 0.0498 (14) | 0.0542 (13) | 0.0310 (11) | 0.0016 (10) | 0.0075 (10) | −0.0134 (10) |
C8 | 0.0330 (11) | 0.0646 (14) | 0.0293 (11) | 0.0056 (10) | 0.0081 (9) | 0.0040 (10) |
C9 | 0.0502 (14) | 0.0527 (13) | 0.0425 (13) | −0.0119 (11) | 0.0142 (11) | 0.0075 (11) |
C10 | 0.0533 (14) | 0.0382 (11) | 0.0381 (12) | −0.0091 (10) | 0.0119 (10) | −0.0050 (9) |
N1 | 0.0462 (10) | 0.0287 (8) | 0.0271 (8) | 0.0056 (7) | 0.0107 (7) | 0.0023 (7) |
N2 | 0.0487 (10) | 0.0299 (8) | 0.0287 (9) | 0.0090 (7) | 0.0103 (8) | 0.0025 (7) |
N3 | 0.0363 (9) | 0.0265 (8) | 0.0253 (8) | 0.0013 (6) | 0.0079 (7) | −0.0016 (6) |
O1 | 0.0652 (10) | 0.0282 (7) | 0.0494 (9) | 0.0057 (7) | 0.0242 (8) | 0.0101 (7) |
O2 | 0.0584 (9) | 0.0334 (7) | 0.0318 (7) | 0.0055 (7) | 0.0205 (7) | 0.0019 (6) |
Cl1 | 0.0569 (4) | 0.1123 (6) | 0.0390 (3) | 0.0133 (4) | 0.0240 (3) | 0.0101 (3) |
Na1 | 0.0500 (5) | 0.0288 (4) | 0.0300 (4) | −0.0048 (3) | 0.0083 (4) | 0.0008 (3) |
Na1—N1i | 2.5649 (16) | C4—H4C | 0.9600 |
Na1—N2ii | 2.5658 (19) | C5—C6 | 1.377 (3) |
Na1—O1iii | 2.3964 (16) | C5—C10 | 1.378 (3) |
Na1—O2 | 2.3299 (14) | C5—N3 | 1.429 (2) |
Na1—O2i | 2.3902 (15) | C6—C7 | 1.380 (3) |
Na1—Na1i | 4.0595 (9) | C6—H6 | 0.9300 |
Na1—Na1iii | 4.0595 (9) | C7—C8 | 1.373 (3) |
C1—O1 | 1.243 (2) | C7—H7 | 0.9300 |
C1—O2 | 1.250 (2) | C8—C9 | 1.376 (3) |
C1—C2 | 1.499 (2) | C8—Cl1 | 1.742 (2) |
C2—N1 | 1.359 (2) | C9—C10 | 1.382 (3) |
C2—C3 | 1.375 (2) | C9—H9 | 0.9300 |
C3—N3 | 1.352 (2) | C10—H10 | 0.9300 |
C3—C4 | 1.478 (3) | N1—N2 | 1.308 (2) |
C4—H4A | 0.9600 | N2—N3 | 1.358 (2) |
C4—H4B | 0.9600 | ||
O1—C1—O2 | 126.89 (17) | N1—N2—N3 | 106.93 (14) |
O1—C1—C2 | 116.76 (16) | N1—N2—Na1iv | 113.55 (12) |
O2—C1—C2 | 116.34 (16) | N3—N2—Na1iv | 119.04 (12) |
O1—C1—Na1 | 85.80 (11) | C3—N3—N2 | 111.00 (14) |
O2—C1—Na1 | 41.15 (9) | C3—N3—C5 | 129.55 (15) |
C2—C1—Na1 | 157.39 (12) | N2—N3—C5 | 119.42 (14) |
N1—C2—C3 | 108.84 (15) | C1—O1—Na1i | 137.58 (14) |
N1—C2—C1 | 121.58 (15) | C1—O2—Na1 | 118.17 (12) |
C3—C2—C1 | 129.59 (17) | C1—O2—Na1iii | 122.42 (11) |
N3—C3—C2 | 104.06 (15) | Na1—O2—Na1iii | 118.64 (6) |
N3—C3—C4 | 124.00 (16) | O2—Na1—O2i | 103.44 (4) |
C2—C3—C4 | 131.76 (18) | O2—Na1—O1iii | 83.35 (5) |
C3—C4—H4A | 109.5 | O2i—Na1—O1iii | 144.50 (7) |
C3—C4—H4B | 109.5 | O2—Na1—N1i | 169.72 (6) |
H4A—C4—H4B | 109.5 | O2i—Na1—N1i | 67.86 (5) |
C3—C4—H4C | 109.5 | O1iii—Na1—N1i | 100.58 (5) |
H4A—C4—H4C | 109.5 | O2—Na1—N2ii | 104.69 (6) |
H4B—C4—H4C | 109.5 | O2i—Na1—N2ii | 123.69 (6) |
C6—C5—C10 | 120.64 (17) | O1iii—Na1—N2ii | 86.61 (6) |
C6—C5—N3 | 120.01 (16) | N1i—Na1—N2ii | 85.11 (5) |
C10—C5—N3 | 119.33 (16) | O2—Na1—C1 | 20.68 (5) |
C5—C6—C7 | 119.56 (18) | O2i—Na1—C1 | 85.20 (5) |
C5—C6—H6 | 120.2 | O1iii—Na1—C1 | 103.90 (5) |
C7—C6—H6 | 120.2 | N1i—Na1—C1 | 152.77 (5) |
C8—C7—C6 | 119.43 (19) | N2ii—Na1—C1 | 107.94 (5) |
C8—C7—H7 | 120.3 | O2—Na1—Na1i | 73.40 (4) |
C6—C7—H7 | 120.3 | O2i—Na1—Na1i | 30.25 (3) |
C7—C8—C9 | 121.55 (18) | O1iii—Na1—Na1i | 140.89 (6) |
C7—C8—Cl1 | 118.84 (17) | N1i—Na1—Na1i | 98.11 (4) |
C9—C8—Cl1 | 119.61 (17) | N2ii—Na1—Na1i | 129.16 (5) |
C8—C9—C10 | 118.82 (19) | C1—Na1—Na1i | 55.00 (4) |
C8—C9—H9 | 120.6 | O2—Na1—Na1iii | 31.12 (4) |
C10—C9—H9 | 120.6 | O2i—Na1—Na1iii | 132.42 (5) |
C5—C10—C9 | 119.99 (19) | O1iii—Na1—Na1iii | 53.76 (3) |
C5—C10—H10 | 120.0 | N1i—Na1—Na1iii | 154.32 (4) |
C9—C10—H10 | 120.0 | N2ii—Na1—Na1iii | 91.80 (4) |
N2—N1—C2 | 109.17 (14) | C1—Na1—Na1iii | 51.60 (4) |
N2—N1—Na1iii | 138.87 (11) | Na1i—Na1—Na1iii | 103.49 (3) |
C2—N1—Na1iii | 109.24 (11) |
Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) x, −y+3/2, z+1/2; (iii) −x, y+1/2, −z+3/2; (iv) x, −y+3/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···N2v | 0.96 | 2.52 | 3.432 (3) | 159 |
Symmetry code: (v) x, y−1, z. |
Funding information
Funding for this research was provided by: King Abdulaziz City for Science and Technology (award No. 20-0180, to MHA).
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