1,3-Bis(2-anilino-2-oxoeth-yl)-1H-imidazol-3-ium chloride dimethyl-formamide monosolvate.

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 imdiazo-lium 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 dimethyl-formamide solvent mol-ecule, 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 = 443.93

Triclinic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.091

S = 1.06

5676 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.20 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812045059/zs2241sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812045059/zs2241Isup3.cml

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

C19H19N4O2+·Cl−·C3H7NO	Z = 2
Mr = 443.93	F(000) = 468
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0418P)2 + 0.3283P] where P = (Fo2 + 2Fc2)/3
5676 reflections	(Δ/σ)max = 0.002
282 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.20 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
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)

	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)

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

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···O3iv	0.95	2.49	3.1619 (13)	128
C12—H12A···Cl1	0.99	2.63	3.4269 (12)	137
C12—H12B···O3iv	0.99	2.44	3.1544 (14)	129
C20—H20A···O4iv	0.99	2.52	3.2790 (15)	133
C23—H23A···O1iv	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

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⋯O3iv	0.95	2.49	3.1619 (13)	128
C12—H12A⋯Cl1	0.99	2.63	3.4269 (12)	137
C12—H12B⋯O3iv	0.99	2.44	3.1544 (14)	129
C20—H20A⋯O4iv	0.99	2.52	3.2790 (15)	133
C23—H23A⋯O1iv	0.98	2.53	3.3472 (18)	141

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .