1-(2-Phenyl-benz-yl)-3-(2,4,6-trimethyl-benz-yl)imidazolidinium bromide.

In the title salt, C(26)H(29)N(2) (+)·Br(-), which may serve as a precursor for N-heterocyclic carbenes, the imidazolidine ring adopts a twist conformation with a pseudo-twofold axis passing through the N-C-N carbon and the opposite C-C bond. The N-C-N bond angle [113.0 (4)°] and C-N bond lengths [1.313 (6) and 1.305 (6) Å] confirm the existence of strong resonance in this part of the mol-ecule. In the crystal, a C-H⋯Br inter-action is present. The dihedral angle between the biphenyl rings is 64.3 (2)° and the phenyl rings make angles of 76.6 (3) and 18.5 (3)° with the plane of the imidazolidine ring.

Related literature

For the synthesis, see: Özdemir et al. (2005b ▶,d ▶). For general background, see: Herrmann (2002 ▶); Scott & Nolan (2005 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶). For related compounds, see: Arduengo et al. (1995a ▶,b ▶); Hagos et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related literature, see: Arslan et al. (2004a ▶,b ▶, 2005a ▶,b ▶, 2007a ▶,b ▶,c ▶); Cavell & Guinness (2004 ▶); Hahn (2006 ▶); Kirmse (2004 ▶); Nair et al. (2004 ▶); Rangits & Kollar (2006 ▶); Richmond (2000 ▶); Özdemir et al. (2004 ▶, 2005a ▶,c ▶).

Experimental

Crystal data

C26H29N2 +·Br−

M = 449.42

Monoclinic,

a = 18.626 (4) Å

b = 13.793 (3) Å

c = 8.8181 (18) Å

β = 95.08 (3)°

V = 2256.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.84 mm−1

T = 183 (2) K

0.36 × 0.19 × 0.12 mm

Data collection

Rigaku AFC-8S Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.615, T max = 0.798

18802 measured reflections

4010 independent reflections

3051 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.241

S = 1.09

4010 reflections

266 parameters

H-atom parameters constrained

Δρmax = 0.75 e Å−3

Δρmin = −1.13 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear (Rigaku/n class="Gene">MSC, 2006 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042086/hg2448sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042086/hg2448Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H29N2+·Br−	F(000) = 936
Mr = 449.42	Dx = 1.323 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8750 reflections
a = 18.626 (4) Å	θ = 2.2–26.0°
b = 13.793 (3) Å	µ = 1.84 mm−1
c = 8.8181 (18) Å	T = 183 K
β = 95.08 (3)°	Rod, colorless
V = 2256.6 (8) Å3	0.36 × 0.19 × 0.12 mm
Z = 4

Rigaku AFC-8S Mercury CCD diffractometer	4010 independent reflections
Radiation source: Sealed Tube	3051 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.060
Detector resolution: 14.6199 pixels mm-1	θmax = 25.1°, θmin = 2.2°
ω scans	h = −22→22
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −16→16
Tmin = 0.615, Tmax = 0.798	l = −10→10
18802 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.241	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.1604P)2 + 1.5464P] where P = (Fo2 + 2Fc2)/3
4010 reflections	(Δ/σ)max = 0.001
266 parameters	Δρmax = 0.75 e Å−3
0 restraints	Δρmin = −1.13 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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.26262 (5)	0.44009 (6)	0.82641 (7)	0.0611 (3)
N1	0.18896 (19)	0.0693 (3)	0.8527 (4)	0.0237 (8)
N2	0.28839 (18)	0.1536 (3)	0.8601 (4)	0.0199 (8)
C1	0.1919 (2)	0.0981 (4)	0.6940 (5)	0.0246 (10)
H1A	0.1486	0.1310	0.6561	0.030*
H1B	0.1990	0.0429	0.6306	0.030*
C2	0.2573 (2)	0.1665 (3)	0.7014 (5)	0.0233 (9)
H2A	0.2908	0.1477	0.6302	0.028*
H2B	0.2427	0.2325	0.6820	0.028*
C3	0.2464 (2)	0.0999 (4)	0.9361 (5)	0.0228 (9)
H3	0.2565	0.0844	1.0420	0.027*
C4	0.3567 (2)	0.1972 (3)	0.9213 (5)	0.0238 (9)
H4A	0.3690	0.1732	1.0225	0.029*
H4B	0.3508	0.2662	0.9277	0.029*
C5	0.4179 (2)	0.1750 (3)	0.8235 (5)	0.0227 (9)
C6	0.4328 (2)	0.0805 (3)	0.7758 (5)	0.0219 (9)
C7	0.4901 (3)	0.0680 (4)	0.6813 (6)	0.0299 (11)
H7	0.5011	0.0042	0.6464	0.036*
C8	0.5299 (3)	0.1449 (5)	0.6396 (6)	0.0355 (12)
H8	0.5685	0.1346	0.5761	0.043*
C9	0.5154 (3)	0.2370 (4)	0.6871 (6)	0.0343 (12)
H9	0.5437	0.2907	0.6574	0.041*
C10	0.4585 (2)	0.2522 (4)	0.7797 (6)	0.0277 (10)
H10	0.4480	0.3166	0.8125	0.033*
C11	0.3903 (2)	−0.0055 (3)	0.8174 (5)	0.0214 (9)
C12	0.3899 (3)	−0.0353 (4)	0.9702 (6)	0.0289 (11)
H12	0.4185	−0.0014	1.0490	0.035*
C13	0.3481 (3)	−0.1133 (4)	1.0064 (6)	0.0340 (11)
H13	0.3475	−0.1326	1.1108	0.041*
C14	0.3074 (3)	−0.1638 (4)	0.8945 (7)	0.0368 (12)
H14	0.2792	−0.2185	0.9211	0.044*
C15	0.3072 (3)	−0.1356 (4)	0.7439 (6)	0.0345 (11)
H15	0.2786	−0.1704	0.6660	0.041*
C16	0.3487 (2)	−0.0567 (3)	0.7052 (5)	0.0247 (10)
H16	0.3485	−0.0375	0.6005	0.030*
C17	0.1316 (2)	0.0098 (4)	0.9081 (6)	0.0260 (10)
H17A	0.1407	0.0013	1.0162	0.031*
H17B	0.1319	−0.0530	0.8614	0.031*
C18	0.0574 (2)	0.0560 (3)	0.8730 (5)	0.0220 (9)
C19	0.0392 (2)	0.1386 (3)	0.9524 (6)	0.0254 (10)
C20	−0.0292 (3)	0.1791 (4)	0.9211 (6)	0.0308 (11)
H20	−0.0419	0.2359	0.9756	0.037*
C21	−0.0789 (2)	0.1391 (4)	0.8132 (6)	0.0326 (11)
C22	−0.0600 (3)	0.0574 (4)	0.7337 (6)	0.0303 (11)
H22	−0.0941	0.0300	0.6574	0.036*
C23	0.0079 (2)	0.0142 (4)	0.7626 (5)	0.0256 (10)
C24	0.0914 (3)	0.1861 (4)	1.0706 (7)	0.0422 (13)
H24A	0.1256	0.2240	1.0207	0.063*
H24B	0.1164	0.1371	1.1320	0.063*
H24C	0.0655	0.2275	1.1341	0.063*
C25	−0.1526 (3)	0.1846 (5)	0.7800 (9)	0.0527 (17)
H25A	−0.1505	0.2329	0.7022	0.079*
H25B	−0.1671	0.2143	0.8709	0.079*
H25C	−0.1868	0.1355	0.7460	0.079*
C26	0.0244 (3)	−0.0751 (4)	0.6756 (7)	0.0387 (12)
H26A	−0.0163	−0.0912	0.6056	0.058*
H26B	0.0344	−0.1279	0.7452	0.058*
H26C	0.0656	−0.0635	0.6201	0.058*

	U11	U22	U33	U12	U13	U23
Br1	0.0930 (6)	0.0614 (5)	0.0280 (4)	0.0157 (4)	0.0006 (3)	−0.0021 (3)
N1	0.0173 (17)	0.032 (2)	0.023 (2)	−0.0009 (15)	0.0085 (15)	0.0097 (16)
N2	0.0164 (16)	0.028 (2)	0.0162 (17)	−0.0001 (14)	0.0043 (14)	0.0024 (15)
C1	0.023 (2)	0.030 (3)	0.020 (2)	−0.0016 (18)	0.0031 (17)	0.0082 (19)
C2	0.021 (2)	0.028 (2)	0.020 (2)	−0.0010 (18)	0.0039 (17)	0.0074 (18)
C3	0.019 (2)	0.030 (2)	0.020 (2)	0.0085 (17)	0.0062 (17)	0.0045 (18)
C4	0.020 (2)	0.027 (2)	0.025 (2)	−0.0013 (18)	0.0031 (17)	−0.0032 (19)
C5	0.020 (2)	0.032 (2)	0.016 (2)	−0.0009 (17)	0.0003 (16)	−0.0022 (18)
C6	0.0178 (19)	0.031 (2)	0.016 (2)	0.0032 (18)	−0.0004 (16)	−0.0007 (18)
C7	0.025 (2)	0.043 (3)	0.022 (2)	0.006 (2)	0.0042 (19)	−0.004 (2)
C8	0.023 (2)	0.061 (4)	0.025 (2)	0.000 (2)	0.0106 (19)	0.000 (2)
C9	0.027 (2)	0.048 (3)	0.028 (3)	−0.015 (2)	0.004 (2)	0.004 (2)
C10	0.024 (2)	0.030 (3)	0.029 (2)	−0.0073 (19)	−0.0001 (18)	−0.002 (2)
C11	0.0178 (19)	0.023 (2)	0.024 (2)	0.0070 (16)	0.0044 (16)	0.0013 (18)
C12	0.028 (2)	0.034 (3)	0.024 (2)	0.0054 (19)	−0.0028 (19)	0.002 (2)
C13	0.033 (2)	0.038 (3)	0.033 (3)	0.009 (2)	0.009 (2)	0.010 (2)
C14	0.028 (2)	0.034 (3)	0.050 (3)	−0.002 (2)	0.008 (2)	0.007 (2)
C15	0.032 (2)	0.035 (3)	0.035 (3)	−0.004 (2)	−0.001 (2)	−0.006 (2)
C16	0.026 (2)	0.025 (2)	0.023 (2)	0.0010 (17)	0.0027 (18)	−0.0029 (18)
C17	0.019 (2)	0.027 (2)	0.033 (3)	0.0019 (18)	0.0091 (19)	0.013 (2)
C18	0.017 (2)	0.022 (2)	0.029 (2)	−0.0015 (16)	0.0125 (18)	0.0053 (17)
C19	0.024 (2)	0.020 (2)	0.033 (2)	−0.0066 (17)	0.0092 (19)	0.0006 (19)
C20	0.032 (2)	0.021 (2)	0.042 (3)	0.0008 (18)	0.018 (2)	0.008 (2)
C21	0.024 (2)	0.032 (3)	0.044 (3)	0.002 (2)	0.015 (2)	0.018 (2)
C22	0.026 (2)	0.041 (3)	0.024 (2)	−0.006 (2)	0.0041 (19)	0.008 (2)
C23	0.030 (2)	0.026 (2)	0.022 (2)	−0.0017 (18)	0.0114 (18)	0.0072 (19)
C24	0.034 (3)	0.040 (3)	0.053 (4)	−0.016 (2)	0.010 (2)	−0.014 (3)
C25	0.026 (3)	0.052 (4)	0.081 (5)	0.015 (3)	0.007 (3)	0.026 (3)
C26	0.047 (3)	0.040 (3)	0.030 (3)	0.002 (2)	0.010 (2)	−0.005 (2)

N1—C3	1.313 (6)	C13—C14	1.379 (8)
N1—C1	1.460 (6)	C13—H13	0.9600
N1—C17	1.465 (6)	C14—C15	1.384 (8)
N2—C3	1.305 (6)	C14—H14	0.9600
N2—C4	1.467 (6)	C15—C16	1.394 (7)
N2—C2	1.477 (6)	C15—H15	0.9600
C1—C2	1.538 (6)	C16—H16	0.9600
C1—H1A	0.9600	C17—C18	1.528 (6)
C1—H1B	0.9600	C17—H17A	0.9600
C2—H2A	0.9600	C17—H17B	0.9600
C2—H2B	0.9600	C18—C19	1.395 (7)
C3—H3	0.9600	C18—C23	1.404 (7)
C4—C5	1.520 (6)	C19—C20	1.395 (7)
C4—H4A	0.9600	C19—C24	1.511 (7)
C4—H4B	0.9600	C20—C21	1.383 (8)
C5—C10	1.382 (7)	C20—H20	0.9600
C5—C6	1.404 (7)	C21—C22	1.390 (8)
C6—C7	1.422 (7)	C21—C25	1.513 (7)
C6—C11	1.490 (6)	C22—C23	1.400 (7)
C7—C8	1.363 (8)	C22—H22	0.9600
C7—H7	0.9600	C23—C26	1.497 (7)
C8—C9	1.371 (8)	C24—H24A	0.9599
C8—H8	0.9600	C24—H24B	0.9599
C9—C10	1.408 (7)	C24—H24C	0.9599
C9—H9	0.9600	C25—H25A	0.9599
C10—H10	0.9600	C25—H25B	0.9599
C11—C16	1.395 (6)	C25—H25C	0.9599
C11—C12	1.409 (7)	C26—H26A	0.9599
C12—C13	1.381 (8)	C26—H26B	0.9599
C12—H12	0.9600	C26—H26C	0.9599
C3—N1—C1	110.6 (4)	C12—C13—H13	119.6
C3—N1—C17	125.2 (4)	C13—C14—C15	119.9 (5)
C1—N1—C17	124.2 (4)	C13—C14—H14	120.0
C3—N2—C4	125.7 (4)	C15—C14—H14	120.0
C3—N2—C2	110.6 (4)	C14—C15—C16	120.0 (5)
C4—N2—C2	123.7 (3)	C14—C15—H15	120.0
N1—C1—C2	102.9 (4)	C16—C15—H15	120.0
N1—C1—H1A	111.2	C15—C16—C11	120.5 (4)
C2—C1—H1A	111.2	C15—C16—H16	119.8
N1—C1—H1B	111.2	C11—C16—H16	119.8
C2—C1—H1B	111.2	N1—C17—C18	111.9 (4)
H1A—C1—H1B	109.1	N1—C17—H17A	109.2
N2—C2—C1	102.1 (3)	C18—C17—H17A	109.2
N2—C2—H2A	111.4	N1—C17—H17B	109.2
C1—C2—H2A	111.4	C18—C17—H17B	109.2
N2—C2—H2B	111.4	H17A—C17—H17B	107.9
C1—C2—H2B	111.4	C19—C18—C23	120.6 (4)
H2A—C2—H2B	109.2	C19—C18—C17	119.6 (4)
N2—C3—N1	113.0 (4)	C23—C18—C17	119.8 (4)
N2—C3—H3	123.5	C18—C19—C20	119.1 (4)
N1—C3—H3	123.5	C18—C19—C24	122.0 (4)
N2—C4—C5	112.2 (4)	C20—C19—C24	118.9 (5)
N2—C4—H4A	109.2	C21—C20—C19	121.4 (5)
C5—C4—H4A	109.2	C21—C20—H20	119.3
N2—C4—H4B	109.2	C19—C20—H20	119.3
C5—C4—H4B	109.2	C20—C21—C22	119.0 (4)
H4A—C4—H4B	107.9	C20—C21—C25	120.6 (5)
C10—C5—C6	120.2 (4)	C22—C21—C25	120.4 (5)
C10—C5—C4	117.4 (4)	C21—C22—C23	121.2 (5)
C6—C5—C4	122.4 (4)	C21—C22—H22	119.4
C5—C6—C7	117.9 (4)	C23—C22—H22	119.4
C5—C6—C11	122.8 (4)	C22—C23—C18	118.6 (5)
C7—C6—C11	119.3 (4)	C22—C23—C26	118.6 (5)
C8—C7—C6	121.1 (5)	C18—C23—C26	122.7 (4)
C8—C7—H7	119.4	C19—C24—H24A	109.5
C6—C7—H7	119.4	C19—C24—H24B	109.5
C7—C8—C9	120.8 (4)	H24A—C24—H24B	109.5
C7—C8—H8	119.6	C19—C24—H24C	109.5
C9—C8—H8	119.6	H24A—C24—H24C	109.5
C8—C9—C10	119.6 (5)	H24B—C24—H24C	109.5
C8—C9—H9	120.2	C21—C25—H25A	109.5
C10—C9—H9	120.2	C21—C25—H25B	109.5
C5—C10—C9	120.4 (5)	H25A—C25—H25B	109.5
C5—C10—H10	119.8	C21—C25—H25C	109.5
C9—C10—H10	119.8	H25A—C25—H25C	109.5
C16—C11—C12	118.7 (4)	H25B—C25—H25C	109.5
C16—C11—C6	120.2 (4)	C23—C26—H26A	109.5
C12—C11—C6	121.1 (4)	C23—C26—H26B	109.5
C13—C12—C11	120.0 (5)	H26A—C26—H26B	109.5
C13—C12—H12	120.0	C23—C26—H26C	109.5
C11—C12—H12	120.0	H26A—C26—H26C	109.5
C14—C13—C12	120.9 (5)	H26B—C26—H26C	109.5
C14—C13—H13	119.6
C3—N1—C1—C2	−8.6 (5)	C16—C11—C12—C13	−0.6 (7)
C17—N1—C1—C2	174.6 (4)	C6—C11—C12—C13	177.8 (4)
C3—N2—C2—C1	−6.8 (5)	C11—C12—C13—C14	1.0 (7)
C4—N2—C2—C1	174.1 (4)	C12—C13—C14—C15	−0.9 (8)
N1—C1—C2—N2	8.7 (4)	C13—C14—C15—C16	0.6 (8)
C4—N2—C3—N1	−179.2 (4)	C14—C15—C16—C11	−0.2 (8)
C2—N2—C3—N1	1.7 (5)	C12—C11—C16—C15	0.2 (7)
C1—N1—C3—N2	4.7 (5)	C6—C11—C16—C15	−178.2 (4)
C17—N1—C3—N2	−178.5 (4)	C3—N1—C17—C18	125.6 (5)
C3—N2—C4—C5	128.7 (5)	C1—N1—C17—C18	−58.0 (6)
C2—N2—C4—C5	−52.3 (6)	N1—C17—C18—C19	−71.4 (6)
N2—C4—C5—C10	129.1 (4)	N1—C17—C18—C23	109.4 (5)
N2—C4—C5—C6	−49.8 (6)	C23—C18—C19—C20	0.3 (7)
C10—C5—C6—C7	−0.4 (6)	C17—C18—C19—C20	−179.0 (4)
C4—C5—C6—C7	178.5 (4)	C23—C18—C19—C24	−179.2 (5)
C10—C5—C6—C11	−179.1 (4)	C17—C18—C19—C24	1.6 (7)
C4—C5—C6—C11	−0.3 (6)	C18—C19—C20—C21	−0.1 (7)
C5—C6—C7—C8	0.6 (7)	C24—C19—C20—C21	179.4 (5)
C11—C6—C7—C8	179.4 (4)	C19—C20—C21—C22	−0.6 (7)
C6—C7—C8—C9	−0.3 (8)	C19—C20—C21—C25	−179.5 (5)
C7—C8—C9—C10	−0.2 (8)	C20—C21—C22—C23	1.0 (7)
C6—C5—C10—C9	−0.1 (7)	C25—C21—C22—C23	180.0 (5)
C4—C5—C10—C9	−179.0 (4)	C21—C22—C23—C18	−0.8 (7)
C8—C9—C10—C5	0.5 (7)	C21—C22—C23—C26	178.6 (5)
C5—C6—C11—C16	114.2 (5)	C19—C18—C23—C22	0.2 (6)
C7—C6—C11—C16	−64.5 (6)	C17—C18—C23—C22	179.4 (4)
C5—C6—C11—C12	−64.2 (6)	C19—C18—C23—C26	−179.2 (4)
C7—C6—C11—C12	117.1 (5)	C17—C18—C23—C26	0.0 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Br1i	0.96	2.52	3.472 (5)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Br1i	0.96	2.52	3.472 (5)	170

Symmetry code: (i) .