Sodium 1-(4-chloro­phen­yl)-5-methyl-1H-1,2,3-triazole-4-carboxyl­ate

El-Hiti, G.A.; Abdel-Wahab, B.F.; Alotaibi, M.H.; Yousif, E.; Hegazy, A.S.; Kariuki, B.M.

doi:10.1107/S2414314618011276

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 8| August 2018| x181127

https://doi.org/10.1107/S2414314618011276

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Sodium 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate

Gamal A. El-Hiti,^a ^* Bakr F. Abdel-Wahab,^b,^c Mohammad Hayal Alotaibi,^d Emad Yousif,^e Amany S. Hegazy ^f and Benson M. Kariuki ^f ^*

^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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 6 August 2018; accepted 7 August 2018; online 14 August 2018)

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 asymmetric unit comprises a Na⁺ 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 coordination polyhedron 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).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯N2ⁱ	0.96	2.52	3.432 (3)	159
Symmetry code: (i) x, y-1, z.

Figure 1
The asymmetric unit of the title salt, showing 50% probability displacement ellisoids.

Figure 2
The crystal packing of the title salt, viewed down the b axis.

Synthesis 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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	Na⁺·C₁₀H₇ClN₃O₂⁻
M_r	259.63
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.6462 (8), 6.3754 (4), 14.7003 (9)
β (°)	92.711 (7)
V (Å³)	1090.26 (12)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.38
Crystal size (mm)	0.42 × 0.16 × 0.07

Data collection
Diffractometer	Rigaku OD SuperNova Dual source diffractometer with an Atlas detector
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.467, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8333, 2665, 1875
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.696

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.115, 1.05
No. of reflections	2665
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.40
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS97 (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1860692

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618011276/hb4252sup1.cif

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

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: 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).

Sodium 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate top

Crystal data top

Na⁺·C₁₀H₇ClN₃O₂⁻	F(000) = 528
M_r = 259.63	D_x = 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

Data collection top

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	1875 reflections with I > 2σ(I)
ω scans	R_int = 0.030
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	θ_max = 29.7°, θ_min = 3.2°
T_min = 0.467, T_max = 1.000	h = −14→15
8333 measured reflections	k = −8→8
2665 independent reflections	l = −20→20

Refinement top

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(F_o²) + (0.0446P)² + 0.2829P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2665 reflections	Δρ_max = 0.25 e Å⁻³
155 parameters	Δρ_min = −0.40 e Å⁻³
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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—Na1^iv	113.55 (12)
O2—C1—C2	116.34 (16)	N3—N2—Na1^iv	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.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···N2^v	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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