1-Ethyl-4-isopropyl-1,2,4-triazolium bromide

Maynard, A.; Keller, T.M.; Gau, M.; Albert, D.R.; Rajaseelan, E.

doi:10.1107/S2414314623007848

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 8| Part 9| September 2023| x230784

https://doi.org/10.1107/S2414314623007848

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1-Ethyl-4-isopropyl-1,2,4-triazolium bromide

Aaron Maynard,^a Taylor M. Keller,^b Michael Gau,^b Daniel R. Albert ^a and Edward Rajaseelan ^a ^*

^aDepartment of Chemistry, Millersville University, Millersville, PA 17551, USA, and ^bDepartment of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, USA
^*Correspondence e-mail: edward.rajaseelan@millersville.edu

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 30 August 2023; accepted 7 September 2023; online 14 September 2023)

An ionic compound consisting of a triazolium cation and bromide anion, C₇H₁₄N₃⁺·Br⁻, has been synthesized and structurally characterized using single-crystal X-ray diffraction and NMR. The compound crystallizes in the monoclinic space group P2₁/m with the non-hydrogen atoms of one cation lying on general positions and the others lying on a mirror plane. One bromide ion also lies on the mirror. The extended structure exhibits only weak intermolecular interactions between heterocyclic C—H groups and Br⁻ ions.

Keywords: crystal structure; triazolium salt; heterocyclic ionic compound.

CCDC reference: 2293675

Structure description

Asymmetric 1,2,4-triazolium cations are of interest due to their utility as cations in ionic liquids (ILs) and as precursors to N-heterocyclic carbenes (NHCs) (Dwivedi et al., 2014 ; Nelson, 2015 ; Strassner et al., 2013 ; Riederer et al., 2011 ; Chianese et al., 2004 ). The crystal structures of several triazolium salts have been reported (Peña Hueso et al., 2022 ; Kumasaki et al., 2021 ; Ponjan et al., 2020 ; Guino-o et al., 2015 ). We have synthesized many imidazolium and triazolium salts as precursors in the synthesis of NHC complexes of rhodium and iridium (Castaldi et al., 2021 ; Gnanamgari et al., 2007 ; Idrees et al., 2017 ; Nichol et al., 2011 ; Newman et al., 2021 ; Rushlow et al., 2022 ).

The molecular structure of the title compound is shown in Fig. 1. There are one and a half molecules in the asymmetric unit with the non-hydrogen atoms of the N1 cation (except C4) and Br1 lying on the (x, 3/4, z) mirror plane. All the atoms of the N4 cation and Br2 occupy general positions. The bond lengths in the triazolium rings indicate aromaticity with C—N bonds exhibiting distances in the range of 1.305 (2)–1.366 (2) Å and N—N bond distances near 1.365 Å; the N—C—N bond angles in the triazolium ring range from 106.93 (18) to 111.35 (18)°. The C1—N2—C5—C6 torsion angle of the ethyl side chain in the N1 cation is constrained to be 0° by symmetry and the corresponding C8—N5—C12—C13 torsion angle in the N4 cation is 24.4 (2)°.

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. The N1 molecule (except C4) and Br1 lie on the (x, 3/4, z) mirror plane. Atom C4ⁱ is generated by the symmetry operation x, $[{3\over 2}]$ − y, z.

The crystal packing of the title compound is displayed in Fig. 2. There are weak non-classical hydrogen-bonding interactions between the heterocyclic C—H groupings and bromide ions. These weak interactions are shown as dotted red lines in Fig. 2 and summarized in Table 1.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Br1ⁱ	0.95	2.67	3.610 (2)	170
C2—H2⋯Br2ⁱ	0.95	2.70	3.6344 (18)	166
C7—H7⋯Br2ⁱ	0.95	2.69	3.6316 (15)	170
C8—H8⋯Br2ⁱ	0.95	2.68	3.5635 (15)	156
Symmetry code: (i) .

Figure 2
Crystal packing of the title compound shown along the a axis. Non-classical C—H⋯Br hydrogen-bonding interactions are shown as dotted red lines.

Synthesis and crystallization

1-Ethyl triazole was purchased from AmBeed. All other compounds used in the syntheses of the title compound were obtained from Sigma-Aldrich. All materials in the synthesis were used as received. The synthesis was performed under nitrogen using reagent grade solvents, which were used as received without further purification. NMR spectra were recorded at room temperature in CDCl₃ on a 400 MHz Varian spectrometer and referenced to the residual solvent peak (δ in p.p.m.).

1-Ethyl-1,2,4-triazole (2.01 g, 20.61 mmol) and isopropyl bromide (10.14 g, 82.4 mmol) were added to toluene (20 ml) and the mixture was refluxed for 48 h. Once cooled, the liquid was decanted, the white solid product that formed was washed with ether, filtered, and dried. The title compound crystallized as clear needles by slow diffusion of pentane into a CH₂Cl₂ solution. Yield: 1.04 g (23%). ¹H NMR: CDCl₃, δ (p.p.m.) 11.99 (s, 1 H, N—C₅H—N), 8.85 (s, 1 H, N—C₃H—N), 5.13 (m, 1 H, CH(CH₃)₂), 4.63 (q, 2 H, N—CH₂), 1.74 (d, 6 H, CH(CH₃)₂), 1.65 (t, 3 H, CH₂CH₃). ¹³C NMR: δ (p.p.m.) 142.27 (N—CH—N), 141.84 (N—CH—N), 53.15 [CH(CH₃)₂], 48.36 (N—CH₂), 23.14 [CH(CH₃)₂], 14.22 (N—CH₂CH₃).

Refinement

Crystal data, data collection, and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₇H₁₄N₃⁺·Br⁻
M_r	220.12
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	100
a, b, c (Å)	8.1283 (2), 21.3822 (7), 8.6376 (2)
β (°)	101.713 (3)
V (Å³)	1469.96 (7)
Z	6
Radiation type	Mo Kα
μ (mm⁻¹)	4.14
Crystal size (mm)	0.38 × 0.25 × 0.04

Data collection
Diffractometer	Rigaku XtaLAB Synergy-S
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD; 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.483, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	23168, 3747, 3142
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.052, 1.04
No. of reflections	3747
No. of parameters	168
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.29
Computer programs: CrysAlis PRO (Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ), and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2293675

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314623007848/hb4448sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314623007848/hb4448Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314623007848/hb4448Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO 1.171.42.79a (Rigaku OD, 2022); cell refinement: CrysAlis PRO 1.171.42.79a (Rigaku OD, 2022); data reduction: CrysAlis PRO 1.171.42.79a (Rigaku OD, 2022); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Olex2 1.3 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

1-Ethyl-4-isopropyl-1,2,4-triazolium bromide top

Crystal data top

C₇H₁₄N₃⁺·Br⁻	F(000) = 672
M_r = 220.12	D_x = 1.492 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
a = 8.1283 (2) Å	Cell parameters from 9609 reflections
b = 21.3822 (7) Å	θ = 3.1–28.2°
c = 8.6376 (2) Å	µ = 4.14 mm⁻¹
β = 101.713 (3)°	T = 100 K
V = 1469.96 (7) Å³	Plate, colourless
Z = 6	0.38 × 0.25 × 0.04 mm

Data collection top

Rigaku XtaLAB Synergy-S diffractometer	3747 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	3142 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.036
Detector resolution: 10.0000 pixels mm^-1	θ_max = 28.3°, θ_min = 2.6°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD; 2022)	k = −27→28
T_min = 0.483, T_max = 1.000	l = −11→11
23168 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.022	H-atom parameters constrained
wR(F²) = 0.052	w = 1/[σ²(F_o²) + (0.0235P)² + 0.254P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3747 reflections	Δρ_max = 0.38 e Å⁻³
168 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.65535 (3)	0.750000	0.86475 (2)	0.01997 (6)
Br2	0.36575 (2)	0.58378 (2)	1.16793 (2)	0.01912 (5)
N1	0.5536 (2)	0.750000	0.34816 (19)	0.0180 (4)
N2	0.3012 (2)	0.750000	0.22004 (19)	0.0181 (4)
N3	0.2904 (2)	0.750000	0.3756 (2)	0.0225 (4)
C1	0.4576 (3)	0.750000	0.2031 (2)	0.0175 (4)
H1	0.495511	0.750000	0.106069	0.021*
C2	0.4471 (3)	0.750000	0.4505 (2)	0.0209 (4)
H2	0.482097	0.750000	0.562368	0.025*
C3	0.7407 (3)	0.750000	0.3888 (3)	0.0277 (5)
H3	0.777584	0.750000	0.506529	0.033*
C4	0.8056 (2)	0.80896 (8)	0.3239 (2)	0.0324 (4)
H4A	0.772489	0.809040	0.208337	0.049*
H4B	0.928441	0.810248	0.355041	0.049*
H4C	0.757925	0.845690	0.366538	0.049*
C5	0.1468 (3)	0.750000	0.0987 (3)	0.0315 (6)
H5A	0.079611	0.787411	0.112921	0.038*	0.5
H5B	0.079611	0.712589	0.112921	0.038*	0.5
C6	0.1791 (3)	0.750000	−0.0638 (3)	0.0353 (6)
H6A	0.225946	0.790528	−0.085598	0.053*	0.5
H6B	0.073605	0.742719	−0.139517	0.053*	0.5
H6C	0.259308	0.716754	−0.073790	0.053*	0.5
N4	0.45707 (16)	0.58697 (5)	0.70657 (14)	0.0163 (3)
N5	0.71989 (15)	0.59178 (5)	0.80363 (14)	0.0170 (3)
N6	0.70540 (17)	0.59818 (6)	0.64405 (15)	0.0234 (3)
C7	0.5439 (2)	0.59462 (7)	0.58810 (18)	0.0223 (3)
H7	0.493358	0.597046	0.478994	0.027*
C8	0.57173 (19)	0.58536 (6)	0.84100 (17)	0.0167 (3)
H8	0.550409	0.580476	0.944460	0.020*
C9	0.27440 (18)	0.57739 (7)	0.69275 (18)	0.0198 (3)
H9	0.249096	0.576878	0.801314	0.024*
C10	0.1780 (2)	0.63095 (8)	0.6001 (2)	0.0296 (4)
H10A	0.218468	0.670794	0.649669	0.044*
H10B	0.057966	0.626396	0.599636	0.044*
H10C	0.195525	0.630178	0.491108	0.044*
C11	0.2264 (2)	0.51438 (8)	0.61529 (19)	0.0287 (4)
H11A	0.240093	0.515644	0.505186	0.043*
H11B	0.109054	0.505046	0.618208	0.043*
H11C	0.299190	0.481809	0.672508	0.043*
C12	0.88457 (19)	0.59542 (8)	0.9095 (2)	0.0242 (3)
H12A	0.917169	0.639848	0.927513	0.029*
H12B	0.969276	0.574799	0.859048	0.029*
C13	0.8832 (2)	0.56445 (8)	1.06588 (18)	0.0246 (3)
H13A	0.847326	0.520823	1.048013	0.037*
H13B	0.804907	0.586585	1.119266	0.037*
H13C	0.996325	0.565779	1.132088	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02633 (12)	0.01928 (12)	0.01483 (11)	0.000	0.00543 (8)	0.000
Br2	0.01946 (8)	0.02267 (9)	0.01542 (8)	−0.00045 (5)	0.00400 (6)	−0.00014 (5)
N1	0.0180 (9)	0.0217 (9)	0.0145 (8)	0.000	0.0036 (7)	0.000
N2	0.0193 (9)	0.0205 (9)	0.0149 (8)	0.000	0.0043 (7)	0.000
N3	0.0242 (10)	0.0261 (10)	0.0194 (9)	0.000	0.0094 (7)	0.000
C1	0.0181 (10)	0.0194 (11)	0.0142 (10)	0.000	0.0015 (8)	0.000
C2	0.0265 (11)	0.0219 (11)	0.0154 (10)	0.000	0.0066 (9)	0.000
C3	0.0196 (11)	0.0469 (15)	0.0148 (10)	0.000	−0.0009 (9)	0.000
C4	0.0238 (8)	0.0396 (10)	0.0359 (9)	−0.0128 (7)	0.0108 (7)	−0.0165 (8)
C5	0.0159 (11)	0.0541 (16)	0.0222 (12)	0.000	−0.0021 (9)	0.000
C6	0.0224 (12)	0.0617 (18)	0.0196 (11)	0.000	−0.0007 (9)	0.000
N4	0.0165 (6)	0.0197 (7)	0.0132 (6)	0.0001 (5)	0.0040 (5)	0.0014 (4)
N5	0.0169 (6)	0.0181 (7)	0.0171 (6)	−0.0005 (5)	0.0059 (5)	0.0009 (4)
N6	0.0244 (7)	0.0275 (7)	0.0204 (7)	−0.0008 (5)	0.0093 (5)	−0.0004 (5)
C7	0.0236 (8)	0.0278 (9)	0.0167 (7)	−0.0001 (6)	0.0068 (6)	−0.0005 (6)
C8	0.0170 (7)	0.0164 (7)	0.0170 (7)	0.0000 (5)	0.0041 (6)	0.0013 (5)
C9	0.0138 (7)	0.0284 (9)	0.0169 (7)	−0.0003 (6)	0.0023 (6)	0.0025 (6)
C10	0.0242 (8)	0.0386 (10)	0.0273 (8)	0.0118 (7)	0.0077 (7)	0.0102 (7)
C11	0.0231 (8)	0.0329 (9)	0.0280 (8)	−0.0061 (7)	0.0003 (7)	−0.0008 (7)
C12	0.0134 (7)	0.0286 (9)	0.0302 (9)	−0.0012 (6)	0.0035 (6)	0.0032 (7)
C13	0.0187 (8)	0.0305 (9)	0.0232 (8)	0.0006 (6)	0.0013 (6)	−0.0004 (6)

Geometric parameters (Å, º) top

N1—C1	1.335 (2)	N4—C7	1.366 (2)
N1—C2	1.357 (3)	N4—C8	1.3337 (19)
N1—C3	1.490 (3)	N4—C9	1.4795 (19)
N2—N3	1.364 (2)	N5—N6	1.3662 (18)
N2—C1	1.308 (3)	N5—C8	1.316 (2)
N2—C5	1.463 (3)	N5—C12	1.4618 (19)
N3—C2	1.307 (3)	N6—C7	1.305 (2)
C3—C4	1.517 (2)	C9—C10	1.520 (2)
C3—C4ⁱ	1.517 (2)	C9—C11	1.520 (2)
C5—C6	1.480 (3)	C12—C13	1.507 (2)

C1—N1—C2	106.43 (18)	C7—N4—C9	128.25 (12)
C1—N1—C3	126.56 (18)	C8—N4—C7	106.21 (13)
C2—N1—C3	127.01 (17)	C8—N4—C9	125.39 (13)
N3—N2—C5	119.20 (18)	N6—N5—C12	120.41 (13)
C1—N2—N3	111.63 (16)	C8—N5—N6	111.24 (12)
C1—N2—C5	129.18 (18)	C8—N5—C12	128.29 (13)
C2—N3—N2	103.67 (18)	C7—N6—N5	104.00 (13)
N2—C1—N1	106.93 (18)	N6—C7—N4	111.31 (13)
N3—C2—N1	111.35 (18)	N5—C8—N4	107.24 (13)
N1—C3—C4ⁱ	109.14 (11)	N4—C9—C10	109.85 (12)
N1—C3—C4	109.14 (11)	N4—C9—C11	108.78 (12)
C4—C3—C4ⁱ	112.4 (2)	C11—C9—C10	112.16 (13)
N2—C5—C6	112.79 (19)	N5—C12—C13	111.39 (13)

N2—N3—C2—N1	0.000 (1)	N5—N6—C7—N4	0.69 (16)
N3—N2—C1—N1	0.000 (1)	N6—N5—C8—N4	0.42 (15)
N3—N2—C5—C6	180.000 (1)	N6—N5—C12—C13	−158.90 (13)
C1—N1—C2—N3	0.000 (1)	C7—N4—C8—N5	0.01 (15)
C1—N1—C3—C4ⁱ	−61.59 (13)	C7—N4—C9—C10	−56.70 (19)
C1—N1—C3—C4	61.59 (13)	C7—N4—C9—C11	66.41 (18)
C1—N2—N3—C2	0.000 (1)	C8—N4—C7—N6	−0.46 (16)
C1—N2—C5—C6	0.000 (1)	C8—N4—C9—C10	128.34 (14)
C2—N1—C1—N2	0.000 (1)	C8—N4—C9—C11	−108.55 (15)
C2—N1—C3—C4ⁱ	118.41 (13)	C8—N5—N6—C7	−0.69 (16)
C2—N1—C3—C4	−118.41 (13)	C8—N5—C12—C13	24.4 (2)
C3—N1—C1—N2	180.000 (1)	C9—N4—C7—N6	−176.18 (13)
C3—N1—C2—N3	180.000 (1)	C9—N4—C8—N5	175.89 (12)
C5—N2—N3—C2	180.000 (1)	C12—N5—N6—C7	−177.94 (13)
C5—N2—C1—N1	180.000 (1)	C12—N5—C8—N4	177.41 (13)

Symmetry code: (i) x, −y+3/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br1ⁱⁱ	0.95	2.67	3.610 (2)	170
C2—H2···Br2ⁱⁱ	0.95	2.70	3.6344 (18)	166
C7—H7···Br2ⁱⁱ	0.95	2.69	3.6316 (15)	170
C8—H8···Br2ⁱⁱ	0.95	2.68	3.5635 (15)	156

Symmetry code: (ii) x, y, z−1.

Acknowledgements

AM was supported in this work by the Millersville University Murley Summer Undergraduate Research Fellowship.

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ISSN: 2414-3146

Volume 8| Part 9| September 2023| x230784

https://doi.org/10.1107/S2414314623007848

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-Ethyl-4-iso­propyl-1,2,4-triazolium bromide

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

1-Ethyl-4-isopropyl-1,2,4-triazolium bromide