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

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.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.022
• wR factor = 0.052
• Data-to-parameter ratio = 22.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT112_ALERT_2_C ADDSYM Detects New (Pseudo) Symm. Elem       b/3         80 %Fit
PLAT761_ALERT_1_C CIF Contains no X-H Bonds ......................     Please Check
PLAT762_ALERT_1_C CIF Contains no X-Y-H or H-Y-H Angles ..........     Please Check

Alert level G
PLAT112_ALERT_2_G ADDSYM Detects New (Pseudo) Symm. Elem       sub         80 %Fit
PLAT300_ALERT_4_G Atom Site Occupancy of H5A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H5B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6C        Constrained at        0.5 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  3  )       0.50 Check
PLAT789_ALERT_4_G Atoms with Negative _atom_site_disorder_group  #          3 Check
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          4 Note
              Br
PLAT822_ALERT_4_G CIF-embedded .res Contains Negative PART Numbers          1 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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

Crystal data

C7H14N3^+·Br^−	F(000) = 672
Mr = 220.12	Dx = 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) Å^3	Plate, colourless
Z = 6	0.38 × 0.25 × 0.04 mm

Data collection

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	Rint = 0.036
Detector resolution: 10.0000 pixels mm^-1	θmax = 28.3°, θmin = 2.6°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD; 2022)	k = −27→28
Tmin = 0.483, Tmax = 1.000	l = −11→11
23168 measured reflections

Refinement

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C4^i	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—C4^i	109.14 (11)	N4—C9—C10	109.85 (12)
N1—C3—C4	109.14 (11)	N4—C9—C11	108.78 (12)
C4—C3—C4^i	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—C4^i	−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—C4^i	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)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br1^ii	0.95	2.67	3.610 (2)	170
C2—H2···Br2^ii	0.95	2.70	3.6344 (18)	166
C7—H7···Br2^ii	0.95	2.69	3.6316 (15)	170
C8—H8···Br2^ii	0.95	2.68	3.5635 (15)	156

Symmetry code: (ii) x, y, z−1.