organic compounds
1,3-Bis(2-anilino-2-oxoethyl)-1H-imidazol-3-ium chloride dimethylformamide monosolvate
aDepartment of Chemistry, National Changhua University of Education, Changhua, Taiwan 50058
*Correspondence e-mail: leehm@cc.ncue.edu.tw
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
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell 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
10.1107/S1600536812045059/zs2241sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812045059/zs2241Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812045059/zs2241Isup3.cml
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.
All of the hydrogen atoms could have been discerned in the difference-Fourier map but were positioned geometrically and refined as riding atoms, with Caryl—H = 0.95, Cmethyl—H = 0.98, Cmethylene—H = 0.99, Cmethine—H = 0.95, and NH = 0.88 Å , with Uiso(H) = 1.2Ueq (Caryl, Cmethylene, Cmethine and N) and Uiso(H) = 1.5 Ueq (Cmethyl).
Data collection: APEX2 (Bruker, 2007); cell
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).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. |
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 |
C19H19N4O2+·Cl−·C3H7NO | γ = 107.224 (3)° |
Mr = 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)° |
Bruker SMART APEXII CCD diffractometer | 5676 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 4849 reflections with I > 2σ(I) |
Tmin = 0.883, Tmax = 0.957 | Rint = 0.018 |
13404 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.27 e Å−3 |
5676 reflections | Δρmin = −0.20 e Å−3 |
282 parameters |
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 |
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 |
Mr | 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) |
Tmin, Tmax | 0.883, 0.957 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13404, 5676, 4849 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.27, −0.20 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2006).
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) −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.
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).