Crystal structure of 1-mesityl-3-methyl-4-phenyl-1H-1,2,3-triazol-3-ium iodide.

In the cation of the title salt, C18H20N3 (+)·I(-), the mesityl and phenyl rings are inclined to the central triazolium ring by 61.39 (16) and 30.99 (16)°, respectively, and to one another by 37.75 (15)°. In the crystal, mol-ecules are linked via C-H⋯I hydrogen bonds, forming slabs parallel to the ab plane. Within the slabs there are weak π-π inter-actions present involving the mesityl and phenyl rings [inter-centroid distances are 3.8663 (18) and 3.8141 (18) Å].

Related literature

For classical Arduengo-type imidazol-2-yl­idene N-heterocyclic carbenes (NHCs), see: Arduengo et al. (1995 ▸); Mathew et al. (2008 ▸). For similar 1-mesityl-3-methyl-4-phenyl-1H-1,2,3-triazol-3-ium structures and some complexes, see: Saravanakumar et al. (2011 ▸); Hohloch et al. (2011 ▸, 2013 ▸); Shaik et al. (2013 ▸).

Experimental

Crystal data

C18H20N3 +·I−

M = 405.27

Monoclinic,

a = 7.6704 (3) Å

b = 9.9341 (3) Å

c = 22.8541 (10) Å

β = 98.982 (4)°

V = 1720.09 (12) Å3

Z = 4

Mo Kα radiation

μ = 1.86 mm−1

T = 130 K

0.14 × 0.08 × 0.02 mm

Data collection

Agilent Xcalibur Atlas Gemini diffractometer

Absorption correction: analytical (CrysAlis RED; Agilent, 2013 ▸) T min = 0.864, T max = 0.963

8948 measured reflections

4073 independent reflections

3374 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.084

S = 1.16

4073 reflections

203 parameters

H-atom parameters constrained

Δρmax = 1.05 e Å−3

Δρmin = −0.57 e Å−3

Data collection: (CrysAlis PRO; Agilent, 2013 ▸); cell refinement: (CrysAlis RED; Agilent, 2013 ▸); data reduction: (CrysAlis RED; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015023403/su5254sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015023403/su5254Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015023403/su5254Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015023403/su5254fig1.tif

The mol­ecular structure of the title salt, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015023403/su5254fig2.tif

A view along the a axis of the crystal packing of the title compound. The C—H⋯I hydrogen bonds are shown as dashed lines (see Table 1). H atoms not involved in these inter­actions have been omitted for clarity.

CCDC reference: 1440705

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H20N3+·I−	F(000) = 808
Mr = 405.27	Dx = 1.565 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3748 reflections
a = 7.6704 (3) Å	θ = 4.5–29.3°
b = 9.9341 (3) Å	µ = 1.86 mm−1
c = 22.8541 (10) Å	T = 130 K
β = 98.982 (4)°	Plate, colourless
V = 1720.09 (12) Å3	0.14 × 0.08 × 0.02 mm
Z = 4

Agilent Xcalibur Atlas Gemini diffractometer	4073 independent reflections
Graphite monochromator	3374 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1	Rint = 0.031
ω scans	θmax = 29.3°, θmin = 3.4°
Absorption correction: analytical (CrysAlis RED; Agilent, 2013)	h = −10→9
Tmin = 0.864, Tmax = 0.963	k = −13→12
8948 measured reflections	l = −20→30

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0324P)2 + 0.4334P] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max = 0.001
4073 reflections	Δρmax = 1.05 e Å−3
203 parameters	Δρmin = −0.57 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
C1	0.9473 (4)	0.6044 (3)	0.32285 (13)	0.0166 (6)
C2	1.0174 (4)	0.7345 (3)	0.32716 (13)	0.0166 (6)
C3	1.0440 (4)	0.7926 (3)	0.38314 (14)	0.0193 (7)
H3	1.0952	0.8798	0.3878	0.023*
C4	0.9986 (4)	0.7281 (3)	0.43240 (14)	0.0207 (7)
C5	0.9244 (4)	0.6001 (3)	0.42536 (14)	0.0205 (7)
H5	0.8905	0.5562	0.4587	0.025*
C6	0.8984 (4)	0.5345 (3)	0.37081 (13)	0.0178 (6)
C7	0.8235 (4)	0.3951 (3)	0.36552 (14)	0.0217 (7)
H7A	0.7477	0.3814	0.3958	0.033*
H7B	0.92	0.3293	0.3712	0.033*
H7C	0.7538	0.3832	0.3261	0.033*
C8	1.0311 (6)	0.7949 (4)	0.49185 (16)	0.0336 (9)
H8A	1.1237	0.7462	0.5179	0.05*
H8B	0.9222	0.7943	0.5093	0.05*
H8C	1.0687	0.8881	0.4873	0.05*
C9	1.0623 (4)	0.8130 (3)	0.27524 (15)	0.0224 (7)
H9A	1.1435	0.8862	0.2896	0.034*
H9B	0.9541	0.8507	0.2527	0.034*
H9C	1.1186	0.7533	0.2496	0.034*
C10	1.0035 (4)	0.4227 (3)	0.25127 (13)	0.0174 (6)
H10	1.0827	0.3672	0.2768	0.021*
C11	0.9446 (4)	0.4023 (3)	0.19207 (13)	0.0165 (6)
C12	0.7388 (4)	0.5467 (3)	0.11771 (13)	0.0193 (7)
H12A	0.8138	0.6043	0.0973	0.029*
H12B	0.6313	0.5958	0.1228	0.029*
H12C	0.707	0.4654	0.0942	0.029*
C13	0.9856 (4)	0.2918 (3)	0.15337 (14)	0.0185 (7)
C14	0.9941 (4)	0.3091 (3)	0.09329 (15)	0.0224 (7)
H14	0.9724	0.3951	0.0755	0.027*
C15	1.0344 (5)	0.2003 (3)	0.05942 (16)	0.0262 (8)
H15	1.0361	0.2112	0.0182	0.031*
C16	1.0722 (4)	0.0760 (3)	0.08598 (16)	0.0265 (8)
H16	1.1002	0.0018	0.0629	0.032*
C17	1.0694 (4)	0.0596 (3)	0.14553 (16)	0.0240 (7)
H17	1.0984	−0.0253	0.1635	0.029*
C18	1.0248 (4)	0.1657 (3)	0.17954 (15)	0.0207 (7)
H18	1.0207	0.153	0.2205	0.025*
I1	0.22531 (3)	0.67415 (2)	0.12660 (2)	0.02384 (9)
N1	0.8211 (3)	0.5913 (3)	0.22025 (11)	0.0174 (5)
N2	0.9259 (3)	0.5380 (2)	0.26597 (10)	0.0152 (5)
N3	0.8348 (3)	0.5089 (2)	0.17589 (11)	0.0157 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0163 (14)	0.0163 (15)	0.0157 (15)	0.0032 (13)	−0.0023 (11)	−0.0023 (13)
C2	0.0134 (14)	0.0184 (16)	0.0174 (15)	0.0047 (13)	0.0006 (11)	0.0015 (13)
C3	0.0193 (15)	0.0152 (15)	0.0223 (17)	0.0029 (13)	−0.0003 (12)	−0.0031 (13)
C4	0.0226 (16)	0.0223 (17)	0.0165 (16)	0.0075 (14)	0.0002 (12)	−0.0011 (14)
C5	0.0250 (16)	0.0217 (17)	0.0149 (15)	0.0047 (14)	0.0029 (12)	0.0048 (13)
C6	0.0167 (14)	0.0170 (15)	0.0189 (15)	0.0040 (13)	0.0005 (12)	0.0016 (13)
C7	0.0251 (16)	0.0163 (16)	0.0234 (17)	0.0000 (14)	0.0025 (13)	0.0055 (13)
C8	0.052 (2)	0.028 (2)	0.0201 (18)	0.0025 (18)	0.0015 (16)	−0.0050 (15)
C9	0.0242 (16)	0.0210 (17)	0.0214 (17)	−0.0020 (14)	0.0016 (13)	0.0014 (14)
C10	0.0198 (15)	0.0141 (15)	0.0177 (15)	0.0032 (13)	0.0010 (12)	0.0000 (12)
C11	0.0160 (14)	0.0130 (15)	0.0199 (16)	−0.0001 (12)	0.0014 (12)	−0.0003 (12)
C12	0.0232 (16)	0.0157 (16)	0.0163 (16)	0.0019 (13)	−0.0050 (12)	0.0008 (12)
C13	0.0156 (14)	0.0148 (15)	0.0242 (17)	0.0005 (13)	0.0006 (12)	−0.0021 (13)
C14	0.0246 (16)	0.0193 (17)	0.0225 (17)	0.0000 (14)	0.0013 (13)	−0.0035 (14)
C15	0.0267 (17)	0.0276 (19)	0.0244 (18)	−0.0022 (15)	0.0040 (14)	−0.0094 (15)
C16	0.0250 (17)	0.0199 (17)	0.035 (2)	−0.0024 (15)	0.0062 (14)	−0.0147 (15)
C17	0.0214 (16)	0.0141 (16)	0.036 (2)	0.0023 (14)	0.0021 (14)	−0.0059 (14)
C18	0.0194 (15)	0.0165 (16)	0.0255 (17)	−0.0009 (13)	0.0015 (13)	−0.0007 (14)
I1	0.02450 (13)	0.01763 (12)	0.03061 (14)	−0.00299 (9)	0.00815 (9)	−0.00440 (9)
N1	0.0191 (13)	0.0143 (13)	0.0179 (13)	0.0005 (11)	0.0004 (10)	−0.0018 (11)
N2	0.0171 (12)	0.0128 (12)	0.0143 (12)	0.0020 (11)	−0.0018 (10)	−0.0006 (10)
N3	0.0188 (12)	0.0112 (12)	0.0158 (12)	−0.0005 (11)	−0.0009 (10)	0.0000 (10)

C1—C6	1.397 (4)	C10—C11	1.373 (4)
C1—C2	1.397 (4)	C10—H10	0.95
C1—N2	1.444 (4)	C11—N3	1.367 (4)
C2—C3	1.389 (4)	C11—C13	1.475 (4)
C2—C9	1.504 (4)	C12—N3	1.465 (4)
C3—C4	1.386 (5)	C12—H12A	0.98
C3—H3	0.95	C12—H12B	0.98
C4—C5	1.392 (5)	C12—H12C	0.98
C4—C8	1.498 (5)	C13—C14	1.395 (5)
C5—C6	1.393 (4)	C13—C18	1.400 (4)
C5—H5	0.95	C14—C15	1.392 (5)
C6—C7	1.497 (4)	C14—H14	0.95
C7—H7A	0.98	C15—C16	1.386 (5)
C7—H7B	0.98	C15—H15	0.95
C7—H7C	0.98	C16—C17	1.374 (5)
C8—H8A	0.98	C16—H16	0.95
C8—H8B	0.98	C17—C18	1.384 (4)
C8—H8C	0.98	C17—H17	0.95
C9—H9A	0.98	C18—H18	0.95
C9—H9B	0.98	N1—N3	1.320 (3)
C9—H9C	0.98	N1—N2	1.325 (3)
C10—N2	1.358 (4)
C6—C1—C2	123.5 (3)	N2—C10—H10	126.9
C6—C1—N2	118.2 (3)	C11—C10—H10	126.9
C2—C1—N2	118.3 (3)	N3—C11—C10	104.3 (3)
C3—C2—C1	116.7 (3)	N3—C11—C13	126.5 (3)
C3—C2—C9	119.5 (3)	C10—C11—C13	129.2 (3)
C1—C2—C9	123.9 (3)	N3—C12—H12A	109.5
C4—C3—C2	122.4 (3)	N3—C12—H12B	109.5
C4—C3—H3	118.8	H12A—C12—H12B	109.5
C2—C3—H3	118.8	N3—C12—H12C	109.5
C3—C4—C5	118.6 (3)	H12A—C12—H12C	109.5
C3—C4—C8	120.3 (3)	H12B—C12—H12C	109.5
C5—C4—C8	121.1 (3)	C14—C13—C18	119.4 (3)
C4—C5—C6	122.0 (3)	C14—C13—C11	123.1 (3)
C4—C5—H5	119	C18—C13—C11	117.5 (3)
C6—C5—H5	119	C15—C14—C13	120.0 (3)
C5—C6—C1	116.8 (3)	C15—C14—H14	120
C5—C6—C7	120.3 (3)	C13—C14—H14	120
C1—C6—C7	122.9 (3)	C16—C15—C14	119.8 (3)
C6—C7—H7A	109.5	C16—C15—H15	120.1
C6—C7—H7B	109.5	C14—C15—H15	120.1
H7A—C7—H7B	109.5	C17—C16—C15	120.3 (3)
C6—C7—H7C	109.5	C17—C16—H16	119.8
H7A—C7—H7C	109.5	C15—C16—H16	119.8
H7B—C7—H7C	109.5	C16—C17—C18	120.6 (3)
C4—C8—H8A	109.5	C16—C17—H17	119.7
C4—C8—H8B	109.5	C18—C17—H17	119.7
H8A—C8—H8B	109.5	C17—C18—C13	119.8 (3)
C4—C8—H8C	109.5	C17—C18—H18	120.1
H8A—C8—H8C	109.5	C13—C18—H18	120.1
H8B—C8—H8C	109.5	N3—N1—N2	104.3 (2)
C2—C9—H9A	109.5	N1—N2—C10	112.2 (2)
C2—C9—H9B	109.5	N1—N2—C1	119.8 (2)
H9A—C9—H9B	109.5	C10—N2—C1	128.0 (2)
C2—C9—H9C	109.5	N1—N3—C11	113.1 (2)
H9A—C9—H9C	109.5	N1—N3—C12	116.7 (2)
H9B—C9—H9C	109.5	C11—N3—C12	130.2 (3)
N2—C10—C11	106.2 (3)
C6—C1—C2—C3	2.3 (4)	C18—C13—C14—C15	2.5 (5)
N2—C1—C2—C3	−177.0 (3)	C11—C13—C14—C15	179.7 (3)
C6—C1—C2—C9	−177.0 (3)	C13—C14—C15—C16	−2.3 (5)
N2—C1—C2—C9	3.8 (4)	C14—C15—C16—C17	0.2 (5)
C1—C2—C3—C4	−2.1 (4)	C15—C16—C17—C18	1.6 (5)
C9—C2—C3—C4	177.2 (3)	C16—C17—C18—C13	−1.3 (5)
C2—C3—C4—C5	0.3 (5)	C14—C13—C18—C17	−0.7 (5)
C2—C3—C4—C8	179.6 (3)	C11—C13—C18—C17	−178.0 (3)
C3—C4—C5—C6	1.4 (5)	N3—N1—N2—C10	−0.7 (3)
C8—C4—C5—C6	−177.9 (3)	N3—N1—N2—C1	178.6 (2)
C4—C5—C6—C1	−1.2 (4)	C11—C10—N2—N1	0.5 (4)
C4—C5—C6—C7	178.0 (3)	C11—C10—N2—C1	−178.8 (3)
C2—C1—C6—C5	−0.7 (4)	C6—C1—N2—N1	119.6 (3)
N2—C1—C6—C5	178.6 (3)	C2—C1—N2—N1	−61.0 (4)
C2—C1—C6—C7	−180.0 (3)	C6—C1—N2—C10	−61.2 (4)
N2—C1—C6—C7	−0.7 (4)	C2—C1—N2—C10	118.1 (3)
N2—C10—C11—N3	0.0 (3)	N2—N1—N3—C11	0.7 (3)
N2—C10—C11—C13	−179.4 (3)	N2—N1—N3—C12	−176.8 (2)
N3—C11—C13—C14	33.1 (5)	C10—C11—N3—N1	−0.5 (3)
C10—C11—C13—C14	−147.6 (3)	C13—C11—N3—N1	179.0 (3)
N3—C11—C13—C18	−149.6 (3)	C10—C11—N3—C12	176.7 (3)
C10—C11—C13—C18	29.7 (5)	C13—C11—N3—C12	−3.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···I1i	0.95	3.12	4.049 (3)	168
C12—H12A···I1ii	0.98	3.20	3.916 (3)	131
C12—H12B···I1	0.98	3.22	4.172 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯I1i	0.95	3.12	4.049 (3)	168
C12—H12A⋯I1ii	0.98	3.20	3.916 (3)	131
C12—H12B⋯I1	0.98	3.22	4.172 (3)	163

Symmetry codes: (i) ; (ii) .