1,3-Bis(2-anilino-2-oxoeth­yl)-1H-imidazol-3-ium chloride acetonitrile monosolvate

Liao, C.-Y.; Lee, H.M.

doi:10.1107/S1600536811048410

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3362

https://doi.org/10.1107/S1600536811048410

Open

access

1,3-Bis(2-anilino-2-oxoethyl)-1H-imidazol-3-ium chloride acetonitrile monosolvate

Chuang-Yi Liao ^a and Hon Man Lee ^a ^*

^aNational Changhua University of Education, Department of Chemistry, Changhua, Taiwan 50058
^*Correspondence e-mail: leehm@cc.ncue.edu.tw

(Received 11 November 2011; accepted 15 November 2011; online 19 November 2011)

In the title compound, C₁₉H₁₉N₄O₂⁺·Cl⁻·C₂H₃N, the dihedral angle between the two phenyl rings is 69.57 (8)° while the dihedral angles between the imidazole ring and the phenyl rings are 70.61 (7) and 82.11 (7)°. In the crystal, N—H⋯Cl, C—H⋯O, C—H⋯Cl and C—H⋯N hydrogen bonds link the imidazolium cations, chloride anions and acetonitrile solvent molecules into a two-dimensional hydrogen-bonded network parallel to (001); an intramolecular C—H⋯O hydrogen bond is also observed.

Related literature

For the crystal structures of nickel, palladium, and silver complexes with ligands derived from the title compound, see: Liao, Chan, Chang et al. (2007 ), Liao, Chan, Zeng et al. (2007 ) and Liao et al. (2008 ), respectively.

Experimental

Crystal data

C₁₉H₁₉N₄O₂⁺·Cl⁻·C₂H₃N
M_r = 411.89
Triclinic, $[P \overline 1]$
a = 8.7801 (6) Å
b = 10.4544 (6) Å
c = 12.1998 (7) Å
α = 91.842 (4)°
β = 95.492 (4)°
γ = 108.096 (4)°
V = 1057.28 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 150 K
0.22 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.956, T_max = 0.970
13815 measured reflections
5067 independent reflections
3597 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.129
S = 1.06
5067 reflections
257 parameters
H-atom parameters constrained
Δρ_max = 0.96 e Å⁻³
Δρ_min = −0.90 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯Cl1ⁱ	0.88	2.28	3.1624 (17)	175
N4—H4⋯Cl1ⁱⁱ	0.88	2.35	3.2287 (17)	175
C4—H4B⋯N5	0.99	2.50	3.262 (3)	134
C12—H12A⋯O1ⁱⁱⁱ	0.99	2.25	3.126 (2)	147
C12—H12B⋯Cl1ⁱⁱⁱ	0.99	2.67	3.400 (2)	131
C19—H19⋯O2	0.95	2.31	2.911 (2)	121
C20—H20A⋯O2	0.98	2.32	3.238 (3)	156
Symmetry codes: (i) x, y-1, z; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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: DIAMOND (Brandenburg, 2006 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811048410/wn2459sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048410/wn2459Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048410/wn2459Isup3.cml

checkCIF report

Comment top

The title compound, C₁₉H₁₉N₄O⁺.Cl^-.C₂H₃N, is a precursor for N-heterocyclic carbene (NHC) ligands. Nickel (Liao, Chan, Chang et al., 2007), palladium (Liao, Chan, Zeng et al., 2007) and silver (Liao et al., 2008) complexes with NHC ligands derived from the salt have been reported by us previously.

The crystal structure of the title compound is shown in Fig. 1. The dihedral angle between the two phenyl rings is 69.57 (8)°; the dihedral angles between the imidazole ring and the phenyl rings are 70.61 (7)° for [C6–C11] and 82.11 (7)° for [C14–C19].

After deprotonation and metal coordination via C2, the N—C—N bond angles become slightly smaller. The N—C—N bond angle in the title compound is 108.59 (17)°, whereas the angles are 105.5 (2) and 106.3 (3) ° in the palladium complex (Liao, Chan, Zeng et al., 2007), 104.4 (4)° in the silver complex (Liao et al., 2008) and 104.9 (4)° in the nickel complex (Liao, Chan, Chang et al., 2007).

One non-classical intramolecular C—H···O hydrogen bond has been detected (Table 1), whereas classical and non-classical intermolecular hydrogen bonds of the type N—H···Cl, C—H···Cl, C—H···O and C—H···N link the imidazolium cations, chloride anions and the acetonitrile molecules into a two-dimensional hydrogen-bonded network (Fig. 2).

Related literature top

For the crystal structures of nickel, palladium, and silver complexes with ligands derived from the title compound, see: Liao, Chan, Chang et al. (2007), Liao, Chan, Zeng et al. (2007) and Liao et al. (2008), respectively.

Experimental top

The compound was prepared according to the literature procedure (Liao, Chan, Zeng et al., 2007). Suitable crystals were obtained by slow diffusion of diethyl ether into an acetonitrile solution of the compound at room temperature.

Structure description top

For the crystal structures of nickel, palladium, and silver complexes with ligands derived from the title compound, see: Liao, Chan, Chang et al. (2007), Liao, Chan, Zeng et al. (2007) and Liao et al. (2008), respectively.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: DIAMOND (Brandenburg, 2006).

Figures top

	Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids for the non-hydrogen atoms. The H atoms are shown as spheres of arbitrary radius.
	Fig. 2. A view of the crystal packing along the c axis, displaying the hydrogen bonds as dashed lines.

1,3-Bis(2-anilino-2-oxoethyl)-1H-imidazol-3-ium chloride acetonitrile monosolvate top

Crystal data top

C₁₉H₁₉N₄O₂⁺·Cl⁻·C₂H₃N	Z = 2
M_r = 411.89	F(000) = 432
Triclinic, P1	D_x = 1.294 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7801 (6) Å	Cell parameters from 2360 reflections
b = 10.4544 (6) Å	θ = 2.5–23.9°
c = 12.1998 (7) Å	µ = 0.21 mm⁻¹
α = 91.842 (4)°	T = 150 K
β = 95.492 (4)°	Block, white
γ = 108.096 (4)°	0.22 × 0.20 × 0.15 mm
V = 1057.28 (11) Å³

Data collection top

Bruker SMART APEXII diffractometer	5067 independent reflections
Radiation source: fine-focus sealed tube	3597 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 28.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −11→11
T_min = 0.956, T_max = 0.970	k = −13→13
13815 measured reflections	l = −16→16

Refinement top

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0538P)² + 0.377P] where P = (F_o² + 2F_c²)/3
5067 reflections	(Δ/σ)_max = 0.001
257 parameters	Δρ_max = 0.96 e Å⁻³
0 restraints	Δρ_min = −0.90 e Å⁻³

Crystal data top

C₁₉H₁₉N₄O₂⁺·Cl⁻·C₂H₃N	γ = 108.096 (4)°
M_r = 411.89	V = 1057.28 (11) Å³
Triclinic, P1	Z = 2
a = 8.7801 (6) Å	Mo Kα radiation
b = 10.4544 (6) Å	µ = 0.21 mm⁻¹
c = 12.1998 (7) Å	T = 150 K
α = 91.842 (4)°	0.22 × 0.20 × 0.15 mm
β = 95.492 (4)°

Data collection top

Bruker SMART APEXII diffractometer	5067 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3597 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.970	R_int = 0.040
13815 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.06	Δρ_max = 0.96 e Å⁻³
5067 reflections	Δρ_min = −0.90 e Å⁻³
257 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.5447 (2)	0.28079 (19)	0.54543 (15)	0.0241 (4)
H1	0.5994	0.2311	0.5071	0.029*
C2	0.3554 (2)	0.3390 (2)	0.62012 (16)	0.0305 (4)
H2	0.2536	0.3360	0.6423	0.037*
C3	0.4941 (2)	0.4426 (2)	0.64010 (17)	0.0310 (5)
H3	0.5086	0.5259	0.6798	0.037*
C4	0.2737 (2)	0.11100 (19)	0.51452 (16)	0.0275 (4)
H4A	0.1824	0.0846	0.5598	0.033*
H4B	0.3256	0.0394	0.5162	0.033*
C5	0.2105 (2)	0.12423 (19)	0.39559 (15)	0.0247 (4)
C6	0.0091 (2)	−0.0133 (2)	0.24692 (16)	0.0261 (4)
C7	−0.0460 (3)	0.0873 (2)	0.20240 (17)	0.0356 (5)
H7	−0.0171	0.1739	0.2400	0.043*
C8	−0.1437 (3)	0.0597 (2)	0.10267 (19)	0.0429 (6)
H8	−0.1814	0.1282	0.0721	0.052*
C9	−0.1872 (3)	−0.0659 (2)	0.04710 (19)	0.0440 (6)
H9	−0.2535	−0.0836	−0.0214	0.053*
C10	−0.1329 (3)	−0.1656 (2)	0.09242 (19)	0.0431 (6)
H10	−0.1628	−0.2523	0.0549	0.052*
C11	−0.0351 (2)	−0.1401 (2)	0.19235 (18)	0.0336 (5)
H11	0.0013	−0.2092	0.2231	0.040*
C12	0.7777 (2)	0.4883 (2)	0.59194 (16)	0.0266 (4)
H12A	0.7821	0.5827	0.5810	0.032*
H12B	0.8238	0.4563	0.5296	0.032*
C13	0.8785 (2)	0.4833 (2)	0.69954 (16)	0.0261 (4)
C14	1.1599 (2)	0.59148 (19)	0.78694 (15)	0.0255 (4)
C15	1.3085 (2)	0.6761 (2)	0.76428 (17)	0.0305 (4)
H15	1.3176	0.7179	0.6961	0.037*
C16	1.4440 (2)	0.7002 (2)	0.84055 (18)	0.0350 (5)
H16	1.5457	0.7569	0.8240	0.042*
C17	1.4306 (3)	0.6414 (2)	0.94059 (18)	0.0380 (5)
H17	1.5229	0.6573	0.9929	0.046*
C18	1.2824 (3)	0.5596 (2)	0.96405 (18)	0.0400 (5)
H18	1.2734	0.5204	1.0333	0.048*
C19	1.1455 (2)	0.5332 (2)	0.88779 (17)	0.0335 (5)
H19	1.0442	0.4762	0.9046	0.040*
C20	0.5812 (3)	0.1257 (3)	0.8373 (2)	0.0472 (4)
H20A	0.6785	0.2017	0.8313	0.071*
H20B	0.6011	0.0734	0.8992	0.071*
H20C	0.4918	0.1598	0.8499	0.071*
C21	0.5404 (3)	0.0403 (3)	0.7362 (2)	0.0472 (4)
Cl1	0.07301 (6)	0.75633 (5)	0.49516 (4)	0.03031 (14)
N1	0.38999 (17)	0.23796 (16)	0.56116 (12)	0.0244 (3)
N2	0.61030 (17)	0.40496 (15)	0.59229 (12)	0.0238 (3)
N3	0.10210 (18)	0.00739 (16)	0.35129 (13)	0.0265 (4)
H3A	0.0878	−0.0630	0.3914	0.032*
N4	1.02870 (18)	0.57136 (16)	0.70405 (13)	0.0263 (4)
H4	1.0477	0.6231	0.6482	0.032*
N5	0.5089 (2)	−0.0260 (2)	0.65673 (17)	0.0439 (5)
O1	0.25525 (16)	0.22902 (13)	0.34914 (11)	0.0291 (3)
O2	0.82600 (17)	0.40675 (16)	0.77037 (12)	0.0387 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0221 (9)	0.0205 (9)	0.0291 (9)	0.0059 (7)	0.0011 (7)	0.0047 (7)
C2	0.0240 (9)	0.0343 (12)	0.0340 (10)	0.0116 (9)	0.0005 (8)	−0.0007 (9)
C3	0.0265 (10)	0.0311 (11)	0.0363 (11)	0.0121 (9)	−0.0005 (8)	−0.0058 (9)
C4	0.0208 (9)	0.0232 (10)	0.0328 (10)	−0.0004 (8)	−0.0012 (7)	0.0044 (8)
C5	0.0168 (8)	0.0237 (10)	0.0329 (10)	0.0055 (7)	0.0011 (7)	0.0022 (8)
C6	0.0183 (8)	0.0273 (10)	0.0304 (10)	0.0042 (8)	0.0008 (7)	0.0031 (8)
C7	0.0351 (11)	0.0306 (12)	0.0392 (11)	0.0118 (9)	−0.0074 (9)	−0.0044 (9)
C8	0.0421 (13)	0.0409 (13)	0.0448 (13)	0.0168 (11)	−0.0129 (10)	0.0025 (10)
C9	0.0399 (13)	0.0430 (14)	0.0411 (12)	0.0076 (11)	−0.0135 (10)	−0.0044 (10)
C10	0.0414 (13)	0.0334 (13)	0.0459 (13)	0.0040 (10)	−0.0075 (10)	−0.0097 (10)
C11	0.0294 (10)	0.0250 (11)	0.0423 (12)	0.0043 (8)	−0.0016 (9)	0.0014 (9)
C12	0.0206 (9)	0.0229 (10)	0.0326 (10)	0.0027 (7)	−0.0024 (7)	0.0042 (8)
C13	0.0224 (9)	0.0241 (10)	0.0302 (10)	0.0061 (8)	−0.0004 (7)	0.0027 (8)
C14	0.0232 (9)	0.0236 (10)	0.0279 (9)	0.0066 (8)	−0.0023 (7)	−0.0008 (8)
C15	0.0269 (10)	0.0291 (11)	0.0323 (10)	0.0048 (8)	0.0010 (8)	0.0010 (8)
C16	0.0223 (10)	0.0343 (12)	0.0431 (12)	0.0033 (9)	−0.0011 (8)	−0.0045 (9)
C17	0.0305 (11)	0.0399 (13)	0.0392 (12)	0.0102 (9)	−0.0124 (9)	−0.0039 (10)
C18	0.0387 (12)	0.0432 (13)	0.0334 (11)	0.0096 (10)	−0.0074 (9)	0.0041 (10)
C19	0.0278 (10)	0.0337 (12)	0.0337 (11)	0.0035 (9)	−0.0016 (8)	0.0047 (9)
C20	0.0476 (10)	0.0426 (10)	0.0472 (10)	0.0069 (8)	0.0084 (8)	0.0076 (8)
C21	0.0476 (10)	0.0426 (10)	0.0472 (10)	0.0069 (8)	0.0084 (8)	0.0076 (8)
Cl1	0.0255 (2)	0.0263 (3)	0.0385 (3)	0.00651 (19)	0.00336 (18)	0.0089 (2)
N1	0.0181 (7)	0.0238 (9)	0.0290 (8)	0.0039 (6)	−0.0009 (6)	0.0038 (6)
N2	0.0186 (7)	0.0217 (8)	0.0298 (8)	0.0061 (6)	−0.0024 (6)	0.0019 (6)
N3	0.0228 (8)	0.0211 (8)	0.0323 (8)	0.0031 (7)	−0.0015 (6)	0.0048 (7)
N4	0.0217 (8)	0.0252 (9)	0.0282 (8)	0.0027 (7)	−0.0015 (6)	0.0071 (7)
N5	0.0382 (11)	0.0497 (13)	0.0481 (12)	0.0195 (9)	0.0047 (9)	0.0088 (10)
O1	0.0266 (7)	0.0229 (7)	0.0345 (7)	0.0035 (6)	0.0012 (6)	0.0061 (6)
O2	0.0291 (8)	0.0409 (9)	0.0363 (8)	−0.0024 (7)	−0.0021 (6)	0.0141 (7)

Geometric parameters (Å, º) top

C1—N1	1.327 (2)	C12—N2	1.458 (2)
C1—N2	1.330 (2)	C12—C13	1.523 (2)
C1—H1	0.9500	C12—H12A	0.9900
C2—C3	1.350 (3)	C12—H12B	0.9900
C2—N1	1.385 (2)	C13—O2	1.221 (2)
C2—H2	0.9500	C13—N4	1.349 (2)
C3—N2	1.373 (2)	C14—C15	1.389 (3)
C3—H3	0.9500	C14—C19	1.390 (3)
C4—N1	1.458 (2)	C14—N4	1.416 (2)
C4—C5	1.529 (3)	C15—C16	1.390 (3)
C4—H4A	0.9900	C15—H15	0.9500
C4—H4B	0.9900	C16—C17	1.383 (3)
C5—O1	1.221 (2)	C16—H16	0.9500
C5—N3	1.352 (2)	C17—C18	1.379 (3)
C6—C11	1.388 (3)	C17—H17	0.9500
C6—C7	1.392 (3)	C18—C19	1.396 (3)
C6—N3	1.417 (2)	C18—H18	0.9500
C7—C8	1.387 (3)	C19—H19	0.9500
C7—H7	0.9500	C20—C21	1.446 (3)
C8—C9	1.383 (3)	C20—H20A	0.9800
C8—H8	0.9500	C20—H20B	0.9800
C9—C10	1.384 (3)	C20—H20C	0.9800
C9—H9	0.9500	C21—N5	1.133 (3)
C10—C11	1.390 (3)	N3—H3A	0.8800
C10—H10	0.9500	N4—H4	0.8800
C11—H11	0.9500

N1—C1—N2	108.59 (17)	H12A—C12—H12B	108.0
N1—C1—H1	125.7	O2—C13—N4	126.00 (17)
N2—C1—H1	125.7	O2—C13—C12	122.57 (17)
C3—C2—N1	106.85 (17)	N4—C13—C12	111.43 (17)
C3—C2—H2	126.6	C15—C14—C19	119.79 (17)
N1—C2—H2	126.6	C15—C14—N4	116.74 (17)
C2—C3—N2	107.19 (17)	C19—C14—N4	123.47 (18)
C2—C3—H3	126.4	C14—C15—C16	120.5 (2)
N2—C3—H3	126.4	C14—C15—H15	119.7
N1—C4—C5	110.81 (15)	C16—C15—H15	119.7
N1—C4—H4A	109.5	C17—C16—C15	119.9 (2)
C5—C4—H4A	109.5	C17—C16—H16	120.1
N1—C4—H4B	109.5	C15—C16—H16	120.1
C5—C4—H4B	109.5	C18—C17—C16	119.65 (18)
H4A—C4—H4B	108.1	C18—C17—H17	120.2
O1—C5—N3	125.89 (17)	C16—C17—H17	120.2
O1—C5—C4	122.59 (16)	C17—C18—C19	121.2 (2)
N3—C5—C4	111.52 (16)	C17—C18—H18	119.4
C11—C6—C7	120.09 (17)	C19—C18—H18	119.4
C11—C6—N3	118.26 (17)	C14—C19—C18	119.0 (2)
C7—C6—N3	121.52 (17)	C14—C19—H19	120.5
C8—C7—C6	119.33 (19)	C18—C19—H19	120.5
C8—C7—H7	120.3	C21—C20—H20A	109.5
C6—C7—H7	120.3	C21—C20—H20B	109.5
C9—C8—C7	121.0 (2)	H20A—C20—H20B	109.5
C9—C8—H8	119.5	C21—C20—H20C	109.5
C7—C8—H8	119.5	H20A—C20—H20C	109.5
C8—C9—C10	119.3 (2)	H20B—C20—H20C	109.5
C8—C9—H9	120.4	N5—C21—C20	179.6 (3)
C10—C9—H9	120.4	C1—N1—C2	108.53 (16)
C9—C10—C11	120.6 (2)	C1—N1—C4	125.20 (16)
C9—C10—H10	119.7	C2—N1—C4	126.02 (16)
C11—C10—H10	119.7	C1—N2—C3	108.84 (16)
C6—C11—C10	119.7 (2)	C1—N2—C12	125.67 (16)
C6—C11—H11	120.2	C3—N2—C12	125.49 (16)
C10—C11—H11	120.2	C5—N3—C6	126.67 (17)
N2—C12—C13	111.46 (16)	C5—N3—H3A	116.7
N2—C12—H12A	109.3	C6—N3—H3A	116.7
C13—C12—H12A	109.3	C13—N4—C14	128.50 (17)
N2—C12—H12B	109.3	C13—N4—H4	115.8
C13—C12—H12B	109.3	C14—N4—H4	115.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Cl1ⁱ	0.88	2.28	3.1624 (17)	175
N4—H4···Cl1ⁱⁱ	0.88	2.35	3.2287 (17)	175
C4—H4B···N5	0.99	2.50	3.262 (3)	134
C12—H12A···O1ⁱⁱⁱ	0.99	2.25	3.126 (2)	147
C12—H12B···Cl1ⁱⁱⁱ	0.99	2.67	3.400 (2)	131
C19—H19···O2	0.95	2.31	2.911 (2)	121
C20—H20A···O2	0.98	2.32	3.238 (3)	156

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉N₄O₂⁺·Cl⁻·C₂H₃N
M_r	411.89
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	8.7801 (6), 10.4544 (6), 12.1998 (7)
α, β, γ (°)	91.842 (4), 95.492 (4), 108.096 (4)
V (Å³)	1057.28 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.22 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.956, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	13815, 5067, 3597
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.129, 1.06
No. of reflections	5067
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.96, −0.90

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Cl1ⁱ	0.88	2.28	3.1624 (17)	175.2
N4—H4···Cl1ⁱⁱ	0.88	2.35	3.2287 (17)	174.8
C4—H4B···N5	0.99	2.50	3.262 (3)	134.0
C12—H12A···O1ⁱⁱⁱ	0.99	2.25	3.126 (2)	147.1
C12—H12B···Cl1ⁱⁱⁱ	0.99	2.67	3.400 (2)	131.0
C19—H19···O2	0.95	2.31	2.911 (2)	120.6
C20—H20A···O2	0.98	2.32	3.238 (3)	155.5

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

Acknowledgements

We thank the National Science Council of Taiwan for financial support of this work.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liao, C.-Y., Chan, K.-T., Chang, Y.-C., Chen, C.-Y., Tu, C.-Y., Hu, C.-H. & Lee, H. M. (2007). Organometallics, 26, 5826–5833. Web of Science CSD CrossRef CAS Google Scholar
Liao, C.-Y., Chan, K.-T., Chiu, P.-L., Chen, C.-Y. & Lee, H. M. (2008). Inorg. Chim. Acta, 361, 2973–2978. Web of Science CSD CrossRef CAS Google Scholar
Liao, C.-Y., Chan, K.-T., Zeng, J.-Y., Hu, C.-H., Tu, C.-Y. & Lee, H. M. (2007). Organometallics, 26, 1692–1702. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3362

https://doi.org/10.1107/S1600536811048410

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1,3-Bis(2-anilino-2-oxoeth­yl)-1H-imidazol-3-ium chloride aceto­nitrile monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,3-Bis(2-anilino-2-oxoethyl)-1H-imidazol-3-ium chloride acetonitrile monosolvate