5-Amino-1-benzyl-4-cyano-3-methyl­imidazolium toluene-p-sulfonate

The title compound, C₁₂H₁₃N₄⁺·C₇H₇O₃S^-, contains an imidazolium cation and a toluene-p-sulfonate anion in the asymmetric unit. Hydrogen-bonded dimers are formed between the cyano and amino groups of inversion-related imidazolium cations.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.050
• wR factor = 0.127
• Data-to-parameter ratio = 23.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm
PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) .....         20 Ang.
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C2      ..       2.96 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and SADABS (Sheldrick, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL.

5-Amino-1-benzyl-4-cyano-3-methylimidazolium toluene-p-sulfonate

Crystal data

C12H13N4^+·C7H7O3S^−	Z = 2
Mr = 384.45	F(000) = 404
Triclinic, P1	Dx = 1.380 Mg m^−3 Dm = 1.368 Mg m^−3 Dm measured by flotation
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8760 (1) Å	Cell parameters from 8192 reflections
b = 7.5163 (1) Å	θ = 1.9–32.9°
c = 21.3393 (2) Å	µ = 0.20 mm^−1
α = 100.047 (1)°	T = 173 K
β = 92.570 (1)°	Plate, colorless
γ = 93.006 (1)°	0.65 × 0.22 × 0.09 mm
V = 925.34 (2) Å^3

Data collection

Siemens SMART CCD area-detector diffractometer	6461 independent reflections
Radiation source: fine-focus sealed tube	4943 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω scans	θmax = 32.9°, θmin = 1.9°
Absorption correction: multi scan (SADABS; Sheldrick, 2002)	h = −8→8
Tmin = 0.879, Tmax = 0.982	k = −11→11
16651 measured reflections	l = −32→32

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0588P)^2 + 0.3521P] where P = (Fo^2 + 2Fc^2)/3
6461 reflections	(Δ/σ)max = 0.001
272 parameters	Δρmax = 0.71 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

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
S1	0.22670 (6)	0.78427 (5)	0.285713 (16)	0.02190 (9)
O1	0.47434 (18)	0.80565 (16)	0.28859 (5)	0.0304 (2)
O2	0.13945 (19)	0.62120 (15)	0.30744 (5)	0.0290 (2)
O3	0.1221 (2)	0.94592 (16)	0.31822 (5)	0.0338 (3)
N1	0.5884 (2)	0.38763 (16)	0.35785 (5)	0.0212 (2)
C2	0.7026 (3)	0.55153 (19)	0.36521 (7)	0.0236 (3)
H2	0.8304	0.5799	0.3422	0.040 (5)*
N3	0.6092 (2)	0.66562 (16)	0.40918 (5)	0.0218 (2)
C3	0.6793 (3)	0.8585 (2)	0.42860 (7)	0.0285 (3)
H3A	0.8054	0.8901	0.4033	0.042 (5)*
H3B	0.7292	0.8828	0.4739	0.034 (5)*
H3C	0.5500	0.9313	0.4216	0.039 (5)*
C4	0.4230 (2)	0.57469 (18)	0.43110 (6)	0.0206 (3)
C6	0.2718 (2)	0.65646 (19)	0.47527 (7)	0.0231 (3)
N5	0.1439 (2)	0.71599 (19)	0.51152 (7)	0.0331 (3)
C5	0.4098 (2)	0.39801 (19)	0.39796 (6)	0.0202 (2)
N4	0.2673 (2)	0.25630 (18)	0.40363 (6)	0.0275 (3)
H41	0.152 (3)	0.283 (2)	0.4262 (9)	0.029 (5)*
H42	0.243 (3)	0.165 (3)	0.3703 (10)	0.037 (5)*
C7	0.6575 (3)	0.22480 (19)	0.31515 (7)	0.0246 (3)
H7A	0.5636	0.1180	0.3226	0.036 (5)*
H7B	0.8189	0.2056	0.3260	0.031 (5)*
C8	0.6318 (2)	0.23823 (18)	0.24533 (6)	0.0207 (3)
C9	0.7978 (3)	0.1675 (2)	0.20516 (7)	0.0253 (3)
H9	0.9287	0.1197	0.2222	0.029 (5)*
C10	0.7712 (3)	0.1671 (2)	0.13972 (7)	0.0302 (3)
H10	0.8839	0.1182	0.1122	0.039 (5)*
C11	0.5811 (3)	0.2377 (2)	0.11479 (7)	0.0314 (3)
H11	0.5632	0.2364	0.0702	0.035 (5)*
C12	0.4167 (3)	0.3104 (2)	0.15484 (8)	0.0302 (3)
H12	0.2875	0.3602	0.1377	0.041 (6)*
C13	0.4408 (3)	0.3103 (2)	0.22007 (7)	0.0254 (3)
H13	0.3276	0.3592	0.2474	0.031 (5)*
C14	0.1347 (2)	0.75941 (17)	0.20410 (6)	0.0199 (2)
C15	−0.0837 (3)	0.6854 (2)	0.18348 (7)	0.0259 (3)
H15	−0.1823	0.6438	0.2127	0.031 (5)*
C16	−0.1566 (3)	0.6728 (2)	0.11976 (7)	0.0288 (3)
H16	−0.3053	0.6216	0.1057	0.046 (6)*
C17	−0.0151 (3)	0.7339 (2)	0.07622 (7)	0.0283 (3)
C18	0.2033 (3)	0.8067 (2)	0.09759 (7)	0.0307 (3)
H18	0.3022	0.8476	0.0683	0.038 (5)*
C19	0.2790 (3)	0.8206 (2)	0.16118 (7)	0.0263 (3)
H19	0.4279	0.8713	0.1752	0.042 (6)*
C20	−0.1006 (4)	0.7257 (3)	0.00752 (8)	0.0423 (4)
H20A	−0.1592	0.8423	0.0025	0.071 (8)*
H20B	−0.2230	0.6302	−0.0037	0.074 (8)*
H20C	0.0252	0.6991	−0.0206	0.095 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.02096 (16)	0.02386 (16)	0.02122 (16)	0.00203 (12)	0.00277 (12)	0.00428 (12)
O1	0.0208 (5)	0.0390 (6)	0.0323 (6)	−0.0008 (4)	−0.0006 (4)	0.0104 (5)
O2	0.0290 (6)	0.0319 (6)	0.0294 (5)	0.0006 (4)	0.0079 (4)	0.0133 (4)
O3	0.0374 (6)	0.0311 (6)	0.0295 (6)	0.0093 (5)	0.0008 (5)	−0.0061 (4)
N1	0.0232 (6)	0.0226 (5)	0.0188 (5)	0.0032 (4)	0.0067 (4)	0.0045 (4)
C2	0.0251 (7)	0.0253 (7)	0.0221 (6)	0.0019 (5)	0.0069 (5)	0.0075 (5)
N3	0.0244 (6)	0.0221 (5)	0.0202 (5)	0.0007 (4)	0.0044 (4)	0.0062 (4)
C3	0.0364 (8)	0.0207 (6)	0.0280 (7)	−0.0034 (6)	0.0027 (6)	0.0049 (5)
C4	0.0210 (6)	0.0227 (6)	0.0187 (6)	0.0018 (5)	0.0050 (5)	0.0049 (5)
C6	0.0234 (7)	0.0223 (6)	0.0232 (6)	0.0009 (5)	0.0026 (5)	0.0026 (5)
N5	0.0318 (7)	0.0316 (7)	0.0348 (7)	0.0024 (6)	0.0108 (6)	0.0006 (5)
C5	0.0209 (6)	0.0241 (6)	0.0164 (6)	0.0026 (5)	0.0039 (5)	0.0046 (5)
N4	0.0276 (6)	0.0256 (6)	0.0279 (6)	−0.0032 (5)	0.0115 (5)	−0.0001 (5)
C7	0.0296 (7)	0.0232 (6)	0.0230 (6)	0.0093 (5)	0.0090 (5)	0.0052 (5)
C8	0.0217 (6)	0.0184 (6)	0.0220 (6)	0.0012 (5)	0.0063 (5)	0.0029 (5)
C9	0.0253 (7)	0.0243 (7)	0.0273 (7)	0.0061 (5)	0.0094 (5)	0.0046 (5)
C10	0.0361 (8)	0.0292 (7)	0.0260 (7)	0.0051 (6)	0.0143 (6)	0.0029 (6)
C11	0.0414 (9)	0.0303 (8)	0.0219 (7)	−0.0012 (6)	0.0038 (6)	0.0034 (6)
C12	0.0302 (8)	0.0314 (8)	0.0290 (7)	0.0038 (6)	−0.0012 (6)	0.0055 (6)
C13	0.0225 (7)	0.0272 (7)	0.0266 (7)	0.0050 (5)	0.0049 (5)	0.0031 (5)
C14	0.0201 (6)	0.0182 (6)	0.0220 (6)	0.0023 (5)	0.0041 (5)	0.0039 (5)
C15	0.0229 (7)	0.0281 (7)	0.0271 (7)	−0.0027 (5)	0.0049 (5)	0.0065 (5)
C16	0.0256 (7)	0.0297 (7)	0.0302 (7)	−0.0025 (6)	−0.0016 (6)	0.0050 (6)
C17	0.0346 (8)	0.0256 (7)	0.0246 (7)	0.0034 (6)	0.0011 (6)	0.0039 (5)
C18	0.0324 (8)	0.0351 (8)	0.0261 (7)	−0.0019 (6)	0.0086 (6)	0.0088 (6)
C19	0.0221 (7)	0.0303 (7)	0.0266 (7)	−0.0024 (5)	0.0056 (5)	0.0051 (5)
C20	0.0522 (11)	0.0465 (10)	0.0280 (8)	0.0026 (9)	−0.0041 (8)	0.0077 (7)

Geometric parameters (Å, º)

S1—O1	1.4529 (11)	C8—C13	1.398 (2)
S1—O2	1.4608 (11)	C9—C10	1.398 (2)
S1—O3	1.4690 (11)	C9—H9	0.9500
S1—C14	1.7752 (14)	C10—C11	1.386 (2)
N1—C2	1.3524 (18)	C10—H10	0.9500
N1—C5	1.3805 (17)	C11—C12	1.389 (2)
N1—C7	1.4795 (17)	C11—H11	0.9500
C2—N3	1.3161 (18)	C12—C13	1.393 (2)
C2—H2	0.9500	C12—H12	0.9500
N3—C4	1.4008 (17)	C13—H13	0.9500
N3—C3	1.4680 (18)	C14—C15	1.392 (2)
C3—H3A	0.9800	C14—C19	1.3945 (19)
C3—H3B	0.9800	C15—C16	1.393 (2)
C3—H3C	0.9800	C15—H15	0.9500
C4—C5	1.3879 (19)	C16—C17	1.394 (2)
C4—C6	1.4092 (19)	C16—H16	0.9500
C6—N5	1.1532 (19)	C17—C18	1.393 (2)
C5—N4	1.3458 (18)	C17—C20	1.518 (2)
N4—H41	0.861 (19)	C18—C19	1.393 (2)
N4—H42	0.90 (2)	C18—H18	0.9500
C7—C8	1.5121 (19)	C19—H19	0.9500
C7—H7A	0.9900	C20—H20A	0.9800
C7—H7B	0.9900	C20—H20B	0.9800
C8—C9	1.3925 (18)	C20—H20C	0.9800
O1—S1—O2	113.47 (7)	C8—C9—C10	119.80 (14)
O1—S1—O3	112.60 (7)	C8—C9—H9	120.1
O2—S1—O3	111.33 (7)	C10—C9—H9	120.1
O1—S1—C14	106.65 (6)	C11—C10—C9	120.24 (14)
O2—S1—C14	106.28 (6)	C11—C10—H10	119.9
O3—S1—C14	105.89 (6)	C9—C10—H10	119.9
C2—N1—C5	109.17 (11)	C10—C11—C12	120.08 (14)
C2—N1—C7	123.61 (11)	C10—C11—H11	120.0
C5—N1—C7	127.16 (12)	C12—C11—H11	120.0
N3—C2—N1	109.40 (12)	C13—C12—C11	120.12 (15)
N3—C2—H2	125.3	C13—C12—H12	119.9
N1—C2—H2	125.3	C11—C12—H12	119.9
C2—N3—C4	108.42 (12)	C12—C13—C8	119.93 (13)
C2—N3—C3	125.53 (12)	C12—C13—H13	120.0
C4—N3—C3	125.93 (12)	C8—C13—H13	120.0
N3—C3—H3A	109.5	C15—C14—C19	120.11 (13)
N3—C3—H3B	109.5	C15—C14—S1	120.16 (10)
H3A—C3—H3B	109.5	C19—C14—S1	119.69 (11)
N3—C3—H3C	109.5	C14—C15—C16	119.53 (13)
H3A—C3—H3C	109.5	C14—C15—H15	120.2
H3B—C3—H3C	109.5	C16—C15—H15	120.2
C5—C4—N3	107.15 (11)	C17—C16—C15	121.16 (14)
C5—C4—C6	128.00 (13)	C17—C16—H16	119.4
N3—C4—C6	124.69 (12)	C15—C16—H16	119.4
N5—C6—C4	177.02 (16)	C18—C17—C16	118.55 (14)
N4—C5—N1	124.02 (12)	C18—C17—C20	121.00 (15)
N4—C5—C4	130.04 (13)	C16—C17—C20	120.42 (15)
N1—C5—C4	105.84 (12)	C19—C18—C17	121.06 (14)
C5—N4—H41	114.9 (13)	C19—C18—H18	119.5
C5—N4—H42	119.0 (13)	C17—C18—H18	119.5
H41—N4—H42	116.3 (18)	C14—C19—C18	119.58 (14)
N1—C7—C8	113.15 (11)	C14—C19—H19	120.2
N1—C7—H7A	108.9	C18—C19—H19	120.2
C8—C7—H7A	108.9	C17—C20—H20A	109.5
N1—C7—H7B	108.9	C17—C20—H20B	109.5
C8—C7—H7B	108.9	H20A—C20—H20B	109.5
H7A—C7—H7B	107.8	C17—C20—H20C	109.5
C9—C8—C13	119.82 (13)	H20A—C20—H20C	109.5
C9—C8—C7	118.45 (13)	H20B—C20—H20C	109.5
C13—C8—C7	121.63 (12)
C5—N1—C2—N3	1.43 (16)	C8—C9—C10—C11	0.4 (2)
C7—N1—C2—N3	−175.91 (12)	C9—C10—C11—C12	0.4 (2)
N1—C2—N3—C4	−1.07 (16)	C10—C11—C12—C13	−0.9 (2)
N1—C2—N3—C3	−177.23 (13)	C11—C12—C13—C8	0.5 (2)
C2—N3—C4—C5	0.31 (16)	C9—C8—C13—C12	0.3 (2)
C3—N3—C4—C5	176.46 (13)	C7—C8—C13—C12	−176.12 (13)
C2—N3—C4—C6	−175.51 (13)	O1—S1—C14—C15	161.42 (11)
C3—N3—C4—C6	0.6 (2)	O2—S1—C14—C15	40.06 (13)
C2—N1—C5—N4	−177.79 (14)	O3—S1—C14—C15	−78.43 (13)
C7—N1—C5—N4	−0.6 (2)	O1—S1—C14—C19	−20.98 (14)
C2—N1—C5—C4	−1.19 (15)	O2—S1—C14—C19	−142.34 (12)
C7—N1—C5—C4	176.03 (13)	O3—S1—C14—C19	99.17 (13)
N3—C4—C5—N4	176.85 (15)	C19—C14—C15—C16	0.1 (2)
C6—C4—C5—N4	−7.5 (3)	S1—C14—C15—C16	177.66 (11)
N3—C4—C5—N1	0.54 (15)	C14—C15—C16—C17	−0.4 (2)
C6—C4—C5—N1	176.18 (14)	C15—C16—C17—C18	0.7 (2)
C2—N1—C7—C8	−67.33 (18)	C15—C16—C17—C20	−177.67 (15)
C5—N1—C7—C8	115.82 (15)	C16—C17—C18—C19	−0.8 (2)
N1—C7—C8—C9	141.50 (13)	C20—C17—C18—C19	177.59 (15)
N1—C7—C8—C13	−42.03 (19)	C15—C14—C19—C18	−0.1 (2)
C13—C8—C9—C10	−0.7 (2)	S1—C14—C19—C18	−177.74 (12)
C7—C8—C9—C10	175.80 (13)	C17—C18—C19—C14	0.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H41···N5^i	0.861 (19)	2.24 (2)	3.0777 (19)	166.2 (17)
N4—H42···O3^ii	0.90 (2)	1.90 (2)	2.7677 (17)	161.3 (19)
C2—H2···O2^iii	0.95	2.02	2.9582 (18)	168
C7—H7A···O1^ii	0.99	2.36	3.2205 (19)	145
C13—H13···O2	0.95	2.49	3.3588 (18)	151
C19—H19···O1	0.95	2.56	2.9263 (19)	103

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y−1, z; (iii) x+1, y, z.