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

Lee, H.M.; Zeng, J.-Y.

doi:10.1107/S1600536812045059

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3286

doi:10.1107/S1600536812045059

Open

access

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

Hon Man Lee ^a ^* and Jing-Yao Zeng ^a

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

(Received 25 October 2012; accepted 31 October 2012; online 3 November 2012)

In the imidazolium cation of the title compound, C₁₉H₁₉N₄O₂⁺·Cl⁻·C₃H₇NO, the dihedral angles between the imidazole ring and the phenyl rings are 85.86 (4) and 70.26 (5)°. In the crystal, N—H⋯Cl hydrogen bonds link the imdiazolium cations and chloride anions into zigzag chains along [110] and together with C—H⋯Cl and C—H⋯O hydrogen bonds, which involve also the dimethylformamide solvent molecule, form a two-dimensional network extending across the ab plane.

Related literature

For the crystal structures of the non-solvated title compound and an acetonitrile monosolvate, see: Liao & Lee (2012 ) and Liao & Lee (2011 ), respectively. 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⁻·C₃H₇NO
M_r = 443.93
Triclinic, $[P \overline 1]$
a = 9.2352 (5) Å
b = 9.9907 (5) Å
c = 14.0805 (7) Å
α = 109.119 (3)°
β = 96.342 (3)°
γ = 107.224 (3)°
V = 1141.05 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 150 K
0.50 × 0.32 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.883, T_max = 0.957
13404 measured reflections
5676 independent reflections
4849 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.091
S = 1.06
5676 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯Cl1ⁱ	0.88	2.39	3.2696 (10)	174
N5—H5⋯Cl1ⁱⁱ	0.88	2.35	3.2292 (10)	172
C1—H1⋯O4ⁱⁱⁱ	0.95	2.32	3.0910 (14)	138
C2—H2⋯O3^iv	0.95	2.49	3.1619 (13)	128
C12—H12A⋯Cl1	0.99	2.63	3.4269 (12)	137
C12—H12B⋯O3^iv	0.99	2.44	3.1544 (14)	129
C20—H20A⋯O4^iv	0.99	2.52	3.2790 (15)	133
C23—H23A⋯O1^iv	0.98	2.53	3.3472 (18)	141
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+2, -z+1; (iii) x, y+1, z; (iv) -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: 10.1107/S1600536812045059/zs2241sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812045059/zs2241Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812045059/zs2241Isup3.cml

checkCIF report

Comment top

The title compound, C₁₉H₁₉N₄O₂⁺.Cl^-.C₃H₇NO, is the dimethylformamide solvate of a reliable ligand precusor for the preparation of transition metal complexes with N-heterocyclic carbene (NHC) ligands. We reported previously the crystal structures of the non-solvated title compound (Liao & Lee 2012) and an acetonitrile monosolvate (Liao & Lee 2011). Transition metal complexes with NHC ligands obtained from the title compound include those with nickel(II) (Liao, Chan, Chang et al. 2007), palladium(II) (Liao, Chan, Zeng et al. 2007) and silver(I) (Liao et al. 2008).

In the structure of the title compound (Fig. 1), the dihedral angles between the heterocyclic ring and the two phenyl rings in the imdiaozlium cation.are 85.86 (4)° and 70.26 (5)° and the molecular conformation is stabilized by intramolecular C7—H···O3 and C15—H···O1 interations. In the crystal, classical intermolecular hydrogen bonds of the type N—H···Cl (Table 1) involving both N4 and N5 link the cations into zigzag chains along the [110] direction and together with non-classical C—H···O and C—H···Cl hydrogen bonds further connect these chains and the DMF solvent molecules into two-dimensional layers lying on the ab plane (Fig. 2).

Related literature top

For the crystal structures of the non-solvated title compound and an acetonitrile monosolvate, see: Liao & Lee (2012) and Liao & Lee (2011), respectively. 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 a DMF solution of the compound at room temperature.

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. The crystal packing viewed down the a axis, displaying the hydrogen bonds as dashed lines.

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

Crystal data top

C₁₉H₁₉N₄O₂⁺·Cl⁻·C₃H₇NO	Z = 2
M_r = 443.93	F(000) = 468
Triclinic, P1	D_x = 1.292 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2352 (5) Å	Cell parameters from 6152 reflections
b = 9.9907 (5) Å	θ = 2.3–28.3°
c = 14.0805 (7) Å	µ = 0.20 mm⁻¹
α = 109.119 (3)°	T = 150 K
β = 96.342 (3)°	Plate, colourless
γ = 107.224 (3)°	0.50 × 0.32 × 0.22 mm
V = 1141.05 (11) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	5676 independent reflections
Radiation source: fine-focus sealed tube	4849 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 28.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −12→12
T_min = 0.883, T_max = 0.957	k = −13→13
13404 measured reflections	l = −18→17

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0418P)² + 0.3283P] where P = (F_o² + 2F_c²)/3
5676 reflections	(Δ/σ)_max = 0.002
282 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₉H₁₉N₄O₂⁺·Cl⁻·C₃H₇NO	γ = 107.224 (3)°
M_r = 443.93	V = 1141.05 (11) Å³
Triclinic, P1	Z = 2
a = 9.2352 (5) Å	Mo Kα radiation
b = 9.9907 (5) Å	µ = 0.20 mm⁻¹
c = 14.0805 (7) Å	T = 150 K
α = 109.119 (3)°	0.50 × 0.32 × 0.22 mm
β = 96.342 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	5676 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	4849 reflections with I > 2σ(I)
T_min = 0.883, T_max = 0.957	R_int = 0.018
13404 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.06	Δρ_max = 0.27 e Å⁻³
5676 reflections	Δρ_min = −0.20 e Å⁻³
282 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	0.45911 (12)	0.71326 (12)	0.46996 (8)	0.0221 (2)
H1	0.4207	0.7855	0.5108	0.027*
C2	0.47374 (13)	0.49834 (12)	0.36866 (9)	0.0242 (2)
H2	0.4457	0.3943	0.3265	0.029*
C3	0.61439 (13)	0.60839 (12)	0.39059 (9)	0.0242 (2)
H3	0.7040	0.5962	0.3672	0.029*
C6	0.96547 (12)	1.12971 (12)	0.77366 (9)	0.0242 (2)
C7	0.99535 (14)	1.04413 (14)	0.82886 (10)	0.0310 (3)
H7	0.9590	0.9368	0.7969	0.037*
C8	1.07892 (16)	1.11709 (17)	0.93125 (11)	0.0392 (3)
H8	1.1012	1.0590	0.9686	0.047*
C9	1.12987 (17)	1.27310 (18)	0.97937 (11)	0.0438 (3)
H9	1.1858	1.3219	1.0495	0.053*
C10	1.09870 (18)	1.35748 (16)	0.92440 (12)	0.0443 (3)
H10	1.1332	1.4646	0.9573	0.053*
C11	1.01746 (15)	1.28717 (14)	0.82159 (11)	0.0334 (3)
H11	0.9975	1.3460	0.7842	0.040*
C12	0.21858 (12)	0.48847 (12)	0.42117 (9)	0.0228 (2)
H12A	0.1854	0.5583	0.4746	0.027*
H12B	0.2138	0.4004	0.4401	0.027*
C13	0.10731 (13)	0.43442 (12)	0.31724 (9)	0.0229 (2)
C14	−0.17305 (13)	0.28559 (12)	0.23667 (9)	0.0265 (2)
C15	−0.17370 (16)	0.27958 (17)	0.13651 (11)	0.0406 (3)
H15	−0.0785	0.3132	0.1169	0.049*
C16	−0.31538 (19)	0.2237 (2)	0.06535 (13)	0.0543 (4)
H16	−0.3164	0.2187	−0.0033	0.065*
C17	−0.45506 (17)	0.17540 (18)	0.09346 (14)	0.0509 (4)
H17	−0.5511	0.1409	0.0450	0.061*
C18	−0.45412 (16)	0.17760 (16)	0.19224 (13)	0.0438 (3)
H18	−0.5495	0.1416	0.2111	0.053*
C19	−0.31349 (15)	0.23256 (15)	0.26377 (11)	0.0350 (3)
H19	−0.3130	0.2340	0.3316	0.042*
C20	0.72883 (13)	0.88905 (12)	0.50232 (9)	0.0242 (2)
H20A	0.6916	0.9693	0.4951	0.029*
H20B	0.8162	0.8883	0.4675	0.029*
C21	0.78517 (12)	0.92260 (12)	0.61644 (9)	0.0224 (2)
C22	0.33318 (17)	0.13837 (18)	0.76265 (14)	0.0485 (4)
H22A	0.2929	0.0459	0.7000	0.073*
H22B	0.2750	0.2049	0.7590	0.073*
H22C	0.3210	0.1118	0.8232	0.073*
C23	0.57161 (19)	0.36610 (16)	0.85242 (11)	0.0437 (3)
H23A	0.6817	0.4056	0.8512	0.066*
H23B	0.5633	0.3596	0.9197	0.066*
H23C	0.5201	0.4341	0.8410	0.066*
C24	0.57427 (14)	0.15345 (14)	0.70631 (10)	0.0287 (2)
H24	0.6815	0.2093	0.7163	0.034*
Cl1	0.04385 (3)	0.75405 (3)	0.48455 (2)	0.02976 (8)
N1	0.60237 (11)	0.74204 (10)	0.45370 (7)	0.02214 (19)
N2	0.37871 (10)	0.56600 (10)	0.41932 (7)	0.02100 (18)
N4	−0.03447 (11)	0.33950 (11)	0.31377 (7)	0.0248 (2)
H4	−0.0412	0.3078	0.3651	0.030*
N5	0.89023 (11)	1.06440 (10)	0.66757 (7)	0.02343 (19)
H5	0.9141	1.1215	0.6314	0.028*
N6	0.49695 (12)	0.21613 (12)	0.77134 (8)	0.0311 (2)
O1	0.14435 (10)	0.47707 (10)	0.24851 (7)	0.0329 (2)
O3	0.73894 (10)	0.82875 (9)	0.65467 (7)	0.02789 (18)
O4	0.51865 (11)	0.02961 (10)	0.63458 (7)	0.0347 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0213 (5)	0.0193 (5)	0.0242 (5)	0.0060 (4)	0.0035 (4)	0.0081 (4)
C2	0.0243 (5)	0.0198 (5)	0.0264 (5)	0.0085 (4)	0.0042 (4)	0.0062 (4)
C3	0.0232 (5)	0.0231 (5)	0.0267 (5)	0.0097 (4)	0.0048 (4)	0.0087 (4)
C6	0.0173 (5)	0.0235 (5)	0.0273 (5)	0.0039 (4)	0.0055 (4)	0.0070 (4)
C7	0.0268 (6)	0.0288 (6)	0.0323 (6)	0.0009 (5)	0.0044 (5)	0.0139 (5)
C8	0.0329 (7)	0.0482 (8)	0.0321 (7)	0.0020 (6)	0.0057 (5)	0.0214 (6)
C9	0.0382 (7)	0.0515 (8)	0.0258 (6)	0.0051 (6)	0.0045 (6)	0.0054 (6)
C10	0.0399 (8)	0.0323 (7)	0.0411 (8)	0.0093 (6)	0.0010 (6)	−0.0047 (6)
C11	0.0283 (6)	0.0246 (6)	0.0396 (7)	0.0089 (5)	0.0014 (5)	0.0050 (5)
C12	0.0187 (5)	0.0229 (5)	0.0255 (5)	0.0043 (4)	0.0038 (4)	0.0104 (4)
C13	0.0212 (5)	0.0213 (5)	0.0253 (5)	0.0067 (4)	0.0043 (4)	0.0088 (4)
C14	0.0214 (5)	0.0226 (5)	0.0304 (6)	0.0050 (4)	0.0018 (4)	0.0073 (4)
C15	0.0293 (7)	0.0486 (8)	0.0348 (7)	0.0011 (6)	0.0003 (5)	0.0180 (6)
C16	0.0431 (9)	0.0620 (10)	0.0418 (8)	0.0000 (7)	−0.0096 (7)	0.0227 (8)
C17	0.0296 (7)	0.0474 (8)	0.0568 (10)	0.0047 (6)	−0.0129 (7)	0.0117 (7)
C18	0.0218 (6)	0.0399 (7)	0.0531 (9)	0.0055 (5)	0.0044 (6)	0.0034 (6)
C19	0.0253 (6)	0.0346 (6)	0.0349 (7)	0.0051 (5)	0.0076 (5)	0.0051 (5)
C20	0.0208 (5)	0.0186 (5)	0.0282 (5)	0.0016 (4)	0.0032 (4)	0.0083 (4)
C21	0.0173 (5)	0.0197 (5)	0.0289 (5)	0.0056 (4)	0.0048 (4)	0.0086 (4)
C22	0.0321 (7)	0.0494 (8)	0.0585 (10)	0.0109 (6)	0.0224 (7)	0.0128 (7)
C23	0.0502 (9)	0.0397 (7)	0.0298 (7)	0.0094 (6)	0.0076 (6)	0.0054 (6)
C24	0.0228 (5)	0.0331 (6)	0.0324 (6)	0.0101 (5)	0.0065 (5)	0.0147 (5)
Cl1	0.03040 (15)	0.02890 (14)	0.03696 (16)	0.01106 (11)	0.01239 (12)	0.01916 (12)
N1	0.0201 (4)	0.0190 (4)	0.0248 (4)	0.0049 (3)	0.0028 (4)	0.0078 (4)
N2	0.0188 (4)	0.0193 (4)	0.0235 (4)	0.0056 (3)	0.0025 (3)	0.0082 (3)
N4	0.0207 (5)	0.0260 (4)	0.0253 (5)	0.0036 (4)	0.0030 (4)	0.0117 (4)
N5	0.0212 (4)	0.0192 (4)	0.0275 (5)	0.0028 (3)	0.0034 (4)	0.0103 (4)
N6	0.0268 (5)	0.0322 (5)	0.0307 (5)	0.0083 (4)	0.0082 (4)	0.0090 (4)
O1	0.0255 (4)	0.0406 (5)	0.0300 (4)	0.0028 (4)	0.0039 (3)	0.0189 (4)
O3	0.0264 (4)	0.0218 (4)	0.0321 (4)	0.0024 (3)	0.0044 (3)	0.0122 (3)
O4	0.0314 (5)	0.0316 (4)	0.0381 (5)	0.0131 (4)	0.0075 (4)	0.0078 (4)

Geometric parameters (Å, º) top

C1—N1	1.3306 (14)	C15—C16	1.392 (2)
C1—N2	1.3316 (13)	C15—H15	0.9500
C1—H1	0.9500	C16—C17	1.387 (2)
C2—C3	1.3545 (16)	C16—H16	0.9500
C2—N2	1.3819 (14)	C17—C18	1.383 (2)
C2—H2	0.9500	C17—H17	0.9500
C3—N1	1.3846 (14)	C18—C19	1.3889 (19)
C3—H3	0.9500	C18—H18	0.9500
C6—C7	1.3924 (17)	C19—H19	0.9500
C6—C11	1.3951 (16)	C20—N1	1.4624 (13)
C6—N5	1.4155 (15)	C20—C21	1.5245 (16)
C7—C8	1.3922 (18)	C20—H20A	0.9900
C7—H7	0.9500	C20—H20B	0.9900
C8—C9	1.383 (2)	C21—O3	1.2229 (13)
C8—H8	0.9500	C21—N5	1.3529 (14)
C9—C10	1.384 (2)	C22—N6	1.4515 (17)
C9—H9	0.9500	C22—H22A	0.9800
C10—C11	1.391 (2)	C22—H22B	0.9800
C10—H10	0.9500	C22—H22C	0.9800
C11—H11	0.9500	C23—N6	1.4552 (17)
C12—N2	1.4598 (14)	C23—H23A	0.9800
C12—C13	1.5201 (15)	C23—H23B	0.9800
C12—H12A	0.9900	C23—H23C	0.9800
C12—H12B	0.9900	C24—O4	1.2268 (15)
C13—O1	1.2215 (14)	C24—N6	1.3319 (16)
C13—N4	1.3550 (14)	C24—H24	0.9500
C14—C15	1.3912 (18)	N4—H4	0.8800
C14—C19	1.3939 (17)	N5—H5	0.8800
C14—N4	1.4172 (14)

N1—C1—N2	108.43 (9)	C16—C17—H17	120.1
N1—C1—H1	125.8	C17—C18—C19	119.86 (14)
N2—C1—H1	125.8	C17—C18—H18	120.1
C3—C2—N2	107.04 (9)	C19—C18—H18	120.1
C3—C2—H2	126.5	C18—C19—C14	120.44 (13)
N2—C2—H2	126.5	C18—C19—H19	119.8
C2—C3—N1	106.80 (10)	C14—C19—H19	119.8
C2—C3—H3	126.6	N1—C20—C21	110.01 (9)
N1—C3—H3	126.6	N1—C20—H20A	109.7
C7—C6—C11	119.90 (11)	C21—C20—H20A	109.7
C7—C6—N5	122.69 (10)	N1—C20—H20B	109.7
C11—C6—N5	117.33 (11)	C21—C20—H20B	109.7
C8—C7—C6	119.49 (12)	H20A—C20—H20B	108.2
C8—C7—H7	120.3	O3—C21—N5	125.42 (11)
C6—C7—H7	120.3	O3—C21—C20	122.24 (10)
C9—C8—C7	120.86 (13)	N5—C21—C20	112.34 (9)
C9—C8—H8	119.6	N6—C22—H22A	109.5
C7—C8—H8	119.6	N6—C22—H22B	109.5
C8—C9—C10	119.40 (13)	H22A—C22—H22B	109.5
C8—C9—H9	120.3	N6—C22—H22C	109.5
C10—C9—H9	120.3	H22A—C22—H22C	109.5
C9—C10—C11	120.73 (13)	H22B—C22—H22C	109.5
C9—C10—H10	119.6	N6—C23—H23A	109.5
C11—C10—H10	119.6	N6—C23—H23B	109.5
C10—C11—C6	119.62 (13)	H23A—C23—H23B	109.5
C10—C11—H11	120.2	N6—C23—H23C	109.5
C6—C11—H11	120.2	H23A—C23—H23C	109.5
N2—C12—C13	111.82 (9)	H23B—C23—H23C	109.5
N2—C12—H12A	109.3	O4—C24—N6	125.49 (12)
C13—C12—H12A	109.3	O4—C24—H24	117.3
N2—C12—H12B	109.3	N6—C24—H24	117.3
C13—C12—H12B	109.3	C1—N1—C3	108.89 (9)
H12A—C12—H12B	107.9	C1—N1—C20	124.81 (9)
O1—C13—N4	126.11 (11)	C3—N1—C20	126.11 (10)
O1—C13—C12	122.49 (10)	C1—N2—C2	108.84 (9)
N4—C13—C12	111.38 (9)	C1—N2—C12	125.25 (9)
C15—C14—C19	119.73 (12)	C2—N2—C12	125.86 (9)
C15—C14—N4	123.11 (11)	C13—N4—C14	127.22 (10)
C19—C14—N4	117.14 (11)	C13—N4—H4	116.4
C14—C15—C16	119.31 (14)	C14—N4—H4	116.4
C14—C15—H15	120.3	C21—N5—C6	126.27 (9)
C16—C15—H15	120.3	C21—N5—H5	116.9
C17—C16—C15	120.81 (15)	C6—N5—H5	116.9
C17—C16—H16	119.6	C24—N6—C22	121.12 (11)
C15—C16—H16	119.6	C24—N6—C23	121.65 (11)
C18—C17—C16	119.81 (14)	C22—N6—C23	117.22 (12)
C18—C17—H17	120.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···Cl1ⁱ	0.88	2.39	3.2696 (10)	174
N5—H5···Cl1ⁱⁱ	0.88	2.35	3.2292 (10)	172
C1—H1···O4ⁱⁱⁱ	0.95	2.32	3.0910 (14)	138
C2—H2···O3^iv	0.95	2.49	3.1619 (13)	128
C12—H12A···Cl1	0.99	2.63	3.4269 (12)	137
C12—H12B···O3^iv	0.99	2.44	3.1544 (14)	129
C20—H20A···O4^iv	0.99	2.52	3.2790 (15)	133
C23—H23A···O1^iv	0.98	2.53	3.3472 (18)	141
C22—H22A···O4	0.98	2.40	2.8049 (18)	104
C15—H15···O1	0.95	2.35	2.9178 (16)	118
C7—H7···O3	0.95	2.39	2.9147 (15)	115

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x, y+1, z; (iv) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉N₄O₂⁺·Cl⁻·C₃H₇NO
M_r	443.93
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	9.2352 (5), 9.9907 (5), 14.0805 (7)
α, β, γ (°)	109.119 (3), 96.342 (3), 107.224 (3)
V (Å³)	1141.05 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.50 × 0.32 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.883, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	13404, 5676, 4849
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.091, 1.06
No. of reflections	5676
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.20

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
N4—H4···Cl1ⁱ	0.88	2.39	3.2696 (10)	174
N5—H5···Cl1ⁱⁱ	0.88	2.35	3.2292 (10)	172
C1—H1···O4ⁱⁱⁱ	0.95	2.32	3.0910 (14)	138
C2—H2···O3^iv	0.95	2.49	3.1619 (13)	128
C12—H12A···Cl1	0.99	2.63	3.4269 (12)	137
C12—H12B···O3^iv	0.99	2.44	3.1544 (14)	129
C20—H20A···O4^iv	0.99	2.52	3.2790 (15)	133
C23—H23A···O1^iv	0.98	2.53	3.3472 (18)	141

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x, y+1, z; (iv) −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
Liao, C.-Y. & Lee, H. M. (2011). Acta Cryst. E67, o3362. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liao, C.-Y. & Lee, H. M. (2012). Acta Cryst. E68, o2232. CSD CrossRef IUCr Journals 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 68| Part 12| December 2012| Page o3286

doi:10.1107/S1600536812045059

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 di­methyl­formamide 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 dimethylformamide monosolvate