1-Benzyl-4,5-di­phenyl-3-vinyl­imidazolium bromide

The title compound, C₂₄H₂₁N₂⁺·Br⁻, contains columns of tetrasubstituted imidazolium cations linked to Br⁻ ions via hydrogen bonding. There is little evidence of π-stacking between cations.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.043
• wR factor = 0.105
• Data-to-parameter ratio = 12.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.95
         From the CIF: _reflns_number_total               3017
         Count of symmetry unique reflns         2005
         Completeness (_total/calc)            150.47%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      1012
         Fraction of Friedel pairs measured     0.505
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).

1-Benzyl-4,5-diphenyl-3-vinylimidazolium bromide

Crystal data

C24H21N2^+·Br^−	Dx = 1.296 Mg m^−3
Mr = 417.34	Melting point: 458 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.883 (2) Å	Cell parameters from 705 reflections
b = 9.440 (2) Å	θ = 3.9–22.3°
c = 11.210 (2) Å	µ = 1.92 mm^−1
β = 111.07 (1)°	T = 298 K
V = 1074.7 (4) Å^3	Rod, pale pink
Z = 2	0.52 × 0.26 × 0.20 mm
F(000) = 428

Data collection

Bruker SMART CCD area-detector diffractometer	3017 independent reflections
Radiation source: fine-focus sealed tube	2259 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Blessing, 1995)	h = −12→7
Tmin = 0.425, Tmax = 0.681	k = −11→10
4474 measured reflections	l = −12→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0649P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
3017 reflections	Δρmax = 0.35 e Å^−3
244 parameters	Δρmin = −0.18 e Å^−3
1 restraint	Absolute structure: Flack (1983); 1196 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.016 (13)

Special details

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.

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

	x	y	z	Uiso*/Ueq
Br1	0.83880 (5)	0.86534 (6)	0.33628 (5)	0.1040 (3)
N3	0.2186 (3)	0.8468 (5)	0.5946 (3)	0.0654 (9)
C4	0.3537 (4)	0.8205 (4)	0.6546 (4)	0.0630 (11)
C51	0.5055 (5)	0.6319 (5)	0.6158 (4)	0.0690 (12)
N1	0.2618 (4)	0.6650 (4)	0.4986 (4)	0.0746 (10)
C2	0.1688 (5)	0.7507 (5)	0.5027 (5)	0.0763 (13)
H2	0.0808	0.7453	0.4494	0.092*
C6	0.2404 (7)	0.5429 (7)	0.4107 (6)	0.112 (2)
H6	0.2405	0.4504	0.4393	0.134*
C5	0.3795 (4)	0.7054 (5)	0.5926 (4)	0.0668 (11)
C7	0.2205 (11)	0.5722 (8)	0.2855 (8)	0.191 (5)
H7A	0.2208	0.6656	0.2592	0.229*
H7B	0.2066	0.4987	0.2269	0.229*
C41	0.4415 (4)	0.8997 (4)	0.7641 (4)	0.0656 (12)
C8	0.1381 (4)	0.9498 (6)	0.6331 (5)	0.0738 (13)
H8A	0.0515	0.9558	0.5667	0.089*
H8B	0.1787	1.0426	0.6421	0.089*
C56	0.5336 (6)	0.5050 (5)	0.6818 (6)	0.0929 (16)
H56	0.4709	0.4615	0.7078	0.111*
C52	0.5989 (5)	0.6902 (6)	0.5759 (5)	0.0851 (14)
H52	0.5793	0.7737	0.5288	0.102*
C54	0.7486 (6)	0.5042 (7)	0.6721 (6)	0.1007 (19)
H54	0.8310	0.4621	0.6932	0.121*
C55	0.6561 (7)	0.4434 (7)	0.7086 (7)	0.1091 (19)
H55	0.6747	0.3580	0.7530	0.131*
C53	0.7212 (6)	0.6298 (8)	0.6027 (6)	0.0996 (18)
H53	0.7836	0.6718	0.5751	0.120*
C46	0.5252 (5)	0.8289 (5)	0.8682 (5)	0.0798 (15)
H46	0.5249	0.7304	0.8690	0.096*
C45	0.6103 (6)	0.9022 (8)	0.9724 (5)	0.107 (2)
H45	0.6685	0.8529	1.0414	0.129*
C43	0.5253 (6)	1.1212 (6)	0.8700 (6)	0.0968 (16)
H43	0.5248	1.2197	0.8712	0.116*
C42	0.4437 (5)	1.0492 (5)	0.7658 (5)	0.0779 (13)
H42	0.3891	1.0992	0.6952	0.093*
C44	0.6087 (6)	1.0465 (9)	0.9737 (6)	0.1069 (19)
H44	0.6641	1.0952	1.0449	0.128*
C21	0.1241 (5)	0.9088 (6)	0.7567 (5)	0.0722 (15)
C24	0.0808 (8)	0.8456 (15)	0.9783 (7)	0.143 (3)
H24	0.0631	0.8263	1.0519	0.172*
C26	0.1442 (7)	1.0089 (8)	0.8490 (7)	0.1056 (19)
H26	0.1723	1.0992	0.8373	0.127*
C25	0.1230 (10)	0.9767 (12)	0.9588 (9)	0.145 (3)
H25	0.1377	1.0456	1.0217	0.175*
C22	0.0859 (6)	0.7765 (8)	0.7768 (7)	0.0997 (19)
H22	0.0738	0.7075	0.7144	0.120*
C23	0.0648 (7)	0.7425 (10)	0.8873 (9)	0.128 (3)
H23	0.0400	0.6511	0.9002	0.153*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0987 (4)	0.0881 (3)	0.0886 (3)	0.0130 (4)	−0.0106 (2)	−0.0091 (3)
N3	0.063 (2)	0.068 (3)	0.0590 (18)	0.007 (2)	0.0144 (15)	−0.002 (2)
C4	0.063 (3)	0.062 (3)	0.060 (2)	0.0001 (18)	0.018 (2)	0.0042 (18)
C51	0.079 (3)	0.060 (3)	0.066 (3)	0.005 (2)	0.025 (2)	−0.001 (2)
N1	0.081 (3)	0.067 (2)	0.064 (2)	−0.002 (2)	0.013 (2)	−0.0065 (18)
C2	0.074 (3)	0.072 (3)	0.069 (3)	0.000 (3)	0.009 (2)	0.005 (2)
C6	0.163 (6)	0.066 (3)	0.084 (4)	0.005 (4)	0.016 (4)	−0.018 (3)
C5	0.076 (3)	0.059 (3)	0.064 (3)	0.002 (2)	0.023 (2)	0.007 (2)
C7	0.378 (16)	0.104 (6)	0.127 (7)	−0.084 (8)	0.137 (9)	−0.054 (5)
C41	0.066 (2)	0.071 (4)	0.056 (2)	−0.001 (2)	0.017 (2)	0.0024 (19)
C8	0.062 (3)	0.073 (3)	0.080 (3)	0.009 (2)	0.018 (2)	0.004 (2)
C56	0.096 (4)	0.070 (3)	0.109 (4)	0.007 (3)	0.033 (3)	0.019 (3)
C52	0.090 (4)	0.075 (3)	0.083 (3)	0.009 (3)	0.022 (3)	0.003 (3)
C54	0.085 (4)	0.103 (5)	0.100 (4)	0.022 (4)	0.016 (3)	−0.024 (4)
C55	0.113 (5)	0.075 (4)	0.139 (5)	0.034 (4)	0.045 (4)	0.022 (4)
C53	0.093 (4)	0.109 (5)	0.097 (4)	0.011 (4)	0.034 (3)	−0.005 (4)
C46	0.083 (3)	0.075 (4)	0.071 (3)	0.007 (2)	0.015 (3)	−0.001 (2)
C45	0.086 (4)	0.136 (8)	0.077 (3)	0.003 (4)	0.002 (3)	−0.002 (4)
C43	0.111 (4)	0.077 (3)	0.096 (4)	−0.016 (3)	0.029 (4)	−0.021 (3)
C42	0.087 (3)	0.066 (3)	0.075 (3)	−0.004 (2)	0.022 (3)	−0.002 (2)
C44	0.093 (4)	0.124 (6)	0.091 (4)	−0.022 (4)	0.018 (3)	−0.034 (4)
C21	0.054 (3)	0.089 (4)	0.070 (3)	0.011 (2)	0.018 (2)	0.008 (3)
C24	0.157 (6)	0.196 (10)	0.096 (5)	0.040 (8)	0.068 (4)	0.035 (7)
C26	0.130 (5)	0.101 (5)	0.094 (4)	0.015 (4)	0.051 (4)	−0.003 (4)
C25	0.198 (9)	0.154 (8)	0.104 (6)	0.032 (7)	0.078 (6)	−0.001 (5)
C22	0.089 (4)	0.110 (5)	0.095 (4)	−0.001 (4)	0.026 (4)	0.017 (4)
C23	0.114 (5)	0.146 (7)	0.124 (6)	−0.014 (5)	0.044 (5)	0.024 (6)

Geometric parameters (Å, º)

N3—C2	1.332 (6)	C54—C55	1.345 (9)
N3—C4	1.402 (5)	C54—C53	1.391 (10)
N3—C8	1.473 (6)	C54—H54	0.930
C4—C5	1.372 (6)	C55—H55	0.930
C4—C41	1.462 (6)	C53—H53	0.930
C51—C52	1.365 (7)	C46—C45	1.387 (7)
C51—C56	1.383 (7)	C46—H46	0.930
C51—C5	1.474 (6)	C45—C44	1.362 (9)
N1—C2	1.310 (6)	C45—H45	0.930
N1—C5	1.389 (6)	C43—C42	1.367 (7)
N1—C6	1.479 (7)	C43—C44	1.383 (9)
C2—H2	0.930	C43—H43	0.930
C6—C7	1.369 (10)	C42—H42	0.930
C6—H6	0.930	C44—H44	0.930
C7—H7A	0.930	C21—C26	1.360 (8)
C7—H7B	0.930	C21—C22	1.360 (8)
C41—C46	1.368 (6)	C24—C25	1.365 (15)
C41—C42	1.411 (6)	C24—C23	1.375 (13)
C8—C21	1.498 (7)	C24—H24	0.930
C8—H8A	0.970	C26—C25	1.365 (11)
C8—H8B	0.970	C26—H26	0.930
C56—C55	1.384 (8)	C25—H25	0.930
C56—H56	0.930	C22—C23	1.377 (10)
C52—C53	1.378 (8)	C22—H22	0.930
C52—H52	0.930	C23—H23	0.930
C2—N3—C4	108.4 (4)	C53—C54—H54	120.0
C2—N3—C8	123.8 (4)	C54—C55—C56	121.5 (6)
C4—N3—C8	127.4 (4)	C54—C55—H55	119.3
C5—C4—N3	105.6 (4)	C56—C55—H55	119.3
C5—C4—C41	129.7 (4)	C52—C53—C54	118.1 (6)
N3—C4—C41	124.7 (4)	C52—C53—H53	121.0
C52—C51—C56	118.4 (5)	C54—C53—H53	121.0
C52—C51—C5	120.5 (4)	C41—C46—C45	120.8 (5)
C56—C51—C5	121.0 (5)	C41—C46—H46	119.6
C2—N1—C5	108.5 (4)	C45—C46—H46	119.6
C2—N1—C6	124.5 (5)	C44—C45—C46	120.1 (6)
C5—N1—C6	126.9 (5)	C44—C45—H45	120.0
N1—C2—N3	110.1 (4)	C46—C45—H45	120.0
N1—C2—H2	125.0	C42—C43—C44	119.5 (6)
N3—C2—H2	125.0	C42—C43—H43	120.2
C7—C6—N1	117.0 (6)	C44—C43—H43	120.2
C7—C6—H6	121.5	C43—C42—C41	120.8 (5)
N1—C6—H6	121.5	C43—C42—H42	119.6
C4—C5—N1	107.5 (4)	C41—C42—H42	119.6
C4—C5—C51	129.1 (4)	C45—C44—C43	120.5 (5)
N1—C5—C51	123.5 (4)	C45—C44—H44	119.8
C6—C7—H7A	120.0	C43—C44—H44	119.8
C6—C7—H7B	120.0	C26—C21—C22	119.2 (6)
H7A—C7—H7B	120.0	C26—C21—C8	118.8 (5)
C46—C41—C42	118.3 (4)	C22—C21—C8	121.9 (5)
C46—C41—C4	120.0 (4)	C25—C24—C23	118.9 (7)
C42—C41—C4	121.7 (4)	C25—C24—H24	120.6
N3—C8—C21	111.7 (4)	C23—C24—H24	120.6
N3—C8—H8A	109.3	C21—C26—C25	119.9 (8)
C21—C8—H8A	109.3	C21—C26—H26	120.1
N3—C8—H8B	109.3	C25—C26—H26	120.1
C21—C8—H8B	109.3	C26—C25—C24	121.5 (9)
H8A—C8—H8B	107.9	C26—C25—H25	119.3
C51—C56—C55	119.4 (6)	C24—C25—H25	119.3
C51—C56—H56	120.3	C21—C22—C23	121.6 (8)
C55—C56—H56	120.3	C21—C22—H22	119.2
C51—C52—C53	122.5 (5)	C23—C22—H22	119.2
C51—C52—H52	118.8	C24—C23—C22	119.0 (8)
C53—C52—H52	118.8	C24—C23—H23	120.5
C55—C54—C53	120.0 (6)	C22—C23—H23	120.5
C55—C54—H54	120.0
C2—N3—C4—C5	0.3 (5)	C4—N3—C8—C21	−68.0 (6)
C8—N3—C4—C5	173.2 (4)	C52—C51—C56—C55	2.0 (8)
C2—N3—C4—C41	−177.1 (4)	C5—C51—C56—C55	−176.1 (5)
C8—N3—C4—C41	−4.2 (7)	C56—C51—C52—C53	−2.3 (8)
C5—N1—C2—N3	0.3 (5)	C5—C51—C52—C53	175.7 (5)
C6—N1—C2—N3	177.9 (5)	C53—C54—C55—C56	−1.8 (10)
C4—N3—C2—N1	−0.4 (6)	C51—C56—C55—C54	0.0 (9)
C8—N3—C2—N1	−173.6 (4)	C51—C52—C53—C54	0.6 (9)
C2—N1—C6—C7	75.4 (9)	C55—C54—C53—C52	1.5 (9)
C5—N1—C6—C7	−107.4 (8)	C42—C41—C46—C45	−0.3 (7)
N3—C4—C5—N1	−0.2 (5)	C4—C41—C46—C45	179.3 (5)
C41—C4—C5—N1	177.1 (4)	C41—C46—C45—C44	2.0 (9)
N3—C4—C5—C51	180.0 (4)	C44—C43—C42—C41	1.5 (8)
C41—C4—C5—C51	−2.8 (7)	C46—C41—C42—C43	−1.4 (7)
C2—N1—C5—C4	−0.1 (5)	C4—C41—C42—C43	179.0 (5)
C6—N1—C5—C4	−177.6 (5)	C46—C45—C44—C43	−1.9 (10)
C2—N1—C5—C51	179.8 (4)	C42—C43—C44—C45	0.2 (10)
C6—N1—C5—C51	2.3 (8)	N3—C8—C21—C26	132.9 (5)
C52—C51—C5—C4	−76.1 (6)	N3—C8—C21—C22	−50.4 (7)
C56—C51—C5—C4	101.9 (6)	C22—C21—C26—C25	−1.5 (10)
C52—C51—C5—N1	104.0 (5)	C8—C21—C26—C25	175.4 (6)
C56—C51—C5—N1	−78.0 (6)	C21—C26—C25—C24	−0.5 (13)
C5—C4—C41—C46	−45.2 (7)	C23—C24—C25—C26	2.8 (14)
N3—C4—C41—C46	131.6 (5)	C26—C21—C22—C23	1.2 (10)
C5—C4—C41—C42	134.3 (5)	C8—C21—C22—C23	−175.6 (6)
N3—C4—C41—C42	−48.9 (6)	C25—C24—C23—C22	−3.0 (13)
C2—N3—C8—C21	103.9 (5)	C21—C22—C23—C24	1.1 (11)