Literature DB >> 22199856

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

Abstract

In the title compound, C(19)H(19)N(4)O(2) (+)·Cl(-)·C(2)H(3)N, 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 mol-ecules into a two-dimensional hydrogen-bonded network parallel to (001); an intra-molecular C-H⋯O hydrogen bond is also observed.

Entities: Chemical Disease Gene

Year: 2011 PMID： 22199856 PMCID： PMC3239007 DOI： 10.1107/S1600536811048410

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

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 = 411.89 Triclinic, 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[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.129 S = 1.06 5067 reflections 257 parameters H-atom parameters constrained Δρmax = 0.96 e Å−3 Δρmin = −0.90 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 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811048410/wn2459sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048410/wn2459Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811048410/wn2459Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

Bruker SMART APEXII diffractometer	5067 independent reflections
Radiation source: fine-focus sealed tube	3597 reflections with I > 2σ(I)
graphite	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 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

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	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)

	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)

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

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.

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) ; (ii) ; (iii) .

1 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

1 in total

2 in total

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

Authors: Hon Man Lee; Jing-Yao Zeng
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-11-03

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

Authors: Chuang-Yi Liao; Hon Man Lee
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-06-27

2 in total