Literature DB >> 21577584

1-Benzyl-3-(2-methoxy-phen-yl)imidazolium tetra-fluoro-borate.

Ping Jiang1.   

Abstract

In the title compound, C(17)H(17)N(2)O(+)·BF(4) (-), the central imidazolium ring makes dihedral angles of 74.58 (9) and 40.10 (6)° with the phenyl and 2-methoxy-phenyl rings, respectively. In the crystal, a strong π-π inter-action is observed between the imidazolium and 2-methoxy-phenyl rings, with a centroid-centroid distance of 3.5115 (15) Å. In addition, C-H⋯F and C-H⋯O hydrogen bonds and C-H⋯π inter-actions involving the -phenyl ring are observed.

Entities:  

Year:  2009        PMID： 21577584      PMCID： PMC2970015          DOI： 10.1107/S1600536809031602

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


Related literature

For the synthesis, see: Liu et al.. (2003 ▶). For general background to N-heterocyclic carbenes, see: Arduengo et al. (1991 ▶). For the biological activity of imidazolium salts, see: Vik et al. (2007 ▶); Demberelnyamba et al. (2004 ▶); Dallas et al. (2007 ▶); Ballistreri et al. (2004 ▶).

Experimental

Crystal data

C17H17N2O+·BF4 − M = 352.14 Orthorhombic, a = 7.1880 (13) Å b = 15.114 (3) Å c = 15.358 (3) Å V = 1668.4 (5) Å3 Z = 4 Mo Kα radiation μ = 0.12 mm−1 T = 93 K 0.40 × 0.33 × 0.33 mm

Data collection

Rigaku SPIDER diffractometer Absorption correction: none 13633 measured reflections 2197 independent reflections 2069 reflections with I > 2σ(I) R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.116 S = 1.00 2197 reflections 227 parameters H-atom parameters constrained Δρmax = 0.85 e Å−3 Δρmin = −0.19 e Å−3 Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031602/ci2870sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031602/ci2870Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H17N2O+·BF4−F(000) = 728
Mr = 352.14Dx = 1.402 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5660 reflections
a = 7.1880 (13) Åθ = 3.0–27.5°
b = 15.114 (3) ŵ = 0.12 mm−1
c = 15.358 (3) ÅT = 93 K
V = 1668.4 (5) Å3Block, colourless
Z = 40.40 × 0.33 × 0.33 mm
Rigaku SPIDER diffractometer2069 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.032
graphiteθmax = 27.5°, θmin = 3.0°
ω scansh = −9→9
13633 measured reflectionsk = −19→19
2197 independent reflectionsl = −19→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.068P)2 + 0.46P] where P = (Fo2 + 2Fc2)/3
2197 reflections(Δ/σ)max = 0.001
227 parametersΔρmax = 0.85 e Å−3
0 restraintsΔρmin = −0.18 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.
xyzUiso*/Ueq
B10.6858 (5)0.1082 (2)0.2432 (2)0.0349 (7)
F10.7005 (2)0.18357 (10)0.29508 (10)0.0360 (4)
F20.7661 (3)0.03715 (11)0.28690 (12)0.0520 (5)
F30.7771 (3)0.12215 (13)0.16519 (11)0.0601 (6)
F40.4996 (3)0.09039 (13)0.22721 (13)0.0555 (6)
O10.6091 (3)0.27395 (12)0.65713 (11)0.0314 (4)
N10.4482 (3)0.45145 (13)0.48559 (13)0.0226 (4)
N20.4930 (3)0.31030 (12)0.49196 (12)0.0203 (4)
C10.6888 (4)0.63622 (15)0.48138 (17)0.0291 (5)
H10.64860.64020.42260.035*
C20.8534 (5)0.67656 (17)0.5060 (2)0.0390 (7)
H20.92620.70750.46420.047*
C30.9113 (5)0.67162 (19)0.5918 (2)0.0453 (8)
H31.02370.69960.60910.054*
C40.8069 (5)0.6263 (2)0.6522 (2)0.0460 (8)
H40.84710.62320.71110.055*
C50.6423 (5)0.58515 (17)0.62717 (18)0.0359 (6)
H50.57100.55350.66890.043*
C60.5814 (4)0.59003 (16)0.54127 (16)0.0264 (5)
C70.4059 (4)0.54316 (16)0.51345 (18)0.0289 (5)
H7A0.31670.54190.56260.035*
H7B0.34750.57580.46470.035*
C80.5203 (3)0.42622 (15)0.40606 (16)0.0230 (5)
H80.54580.46380.35790.028*
C90.5478 (3)0.33788 (15)0.40976 (15)0.0211 (5)
H90.59560.30150.36460.025*
C100.4336 (3)0.38076 (16)0.53617 (15)0.0227 (5)
H100.38830.38030.59430.027*
C110.4976 (3)0.22050 (15)0.52293 (15)0.0213 (5)
C120.4486 (3)0.15283 (16)0.46744 (16)0.0235 (5)
H120.41160.16570.40940.028*
C130.4533 (3)0.06574 (16)0.49642 (18)0.0288 (5)
H130.42080.01880.45820.035*
C140.5056 (4)0.04793 (17)0.58102 (19)0.0317 (6)
H140.5070−0.01160.60100.038*
C150.5562 (3)0.11531 (17)0.63726 (18)0.0305 (6)
H150.59180.10190.69530.037*
C160.5549 (3)0.20287 (16)0.60874 (15)0.0246 (5)
C170.6499 (5)0.2592 (2)0.74763 (17)0.0423 (7)
H17A0.53850.23690.77710.051*
H17B0.68850.31510.77460.051*
H17C0.75040.21580.75290.051*
U11U22U33U12U13U23
B10.0408 (16)0.0351 (15)0.0287 (15)0.0150 (14)−0.0110 (14)−0.0110 (13)
F10.0441 (9)0.0332 (8)0.0308 (8)0.0046 (7)0.0012 (7)−0.0122 (7)
F20.0711 (13)0.0394 (9)0.0455 (11)0.0217 (9)−0.0260 (10)−0.0105 (8)
F30.0828 (15)0.0669 (13)0.0306 (10)0.0258 (12)0.0078 (10)−0.0132 (9)
F40.0473 (10)0.0555 (11)0.0638 (13)0.0119 (10)−0.0236 (10)−0.0256 (10)
O10.0325 (10)0.0403 (10)0.0214 (9)−0.0103 (8)−0.0031 (8)0.0036 (7)
N10.0221 (9)0.0230 (9)0.0228 (10)0.0009 (8)0.0009 (8)−0.0030 (8)
N20.0206 (9)0.0208 (9)0.0194 (9)−0.0025 (7)0.0009 (8)0.0011 (7)
C10.0393 (13)0.0219 (10)0.0261 (13)0.0020 (11)−0.0057 (11)0.0006 (10)
C20.0464 (16)0.0290 (13)0.0415 (16)−0.0099 (12)−0.0037 (14)0.0027 (11)
C30.0506 (18)0.0347 (14)0.0504 (18)−0.0131 (13)−0.0161 (15)−0.0031 (13)
C40.065 (2)0.0432 (16)0.0298 (15)−0.0067 (16)−0.0153 (15)−0.0046 (13)
C50.0518 (17)0.0313 (12)0.0245 (13)−0.0014 (13)0.0000 (13)−0.0046 (10)
C60.0333 (13)0.0212 (10)0.0247 (12)0.0035 (10)−0.0001 (10)−0.0039 (9)
C70.0308 (12)0.0237 (11)0.0321 (14)0.0052 (10)0.0025 (11)−0.0077 (10)
C80.0252 (11)0.0238 (10)0.0200 (11)−0.0005 (9)0.0021 (10)−0.0004 (9)
C90.0220 (11)0.0225 (10)0.0187 (11)0.0002 (9)0.0019 (9)0.0000 (9)
C100.0214 (10)0.0265 (11)0.0202 (11)−0.0009 (9)0.0030 (9)−0.0009 (9)
C110.0150 (9)0.0244 (10)0.0245 (12)−0.0011 (9)0.0010 (9)0.0044 (9)
C120.0181 (10)0.0250 (11)0.0275 (13)0.0007 (9)−0.0002 (9)0.0017 (9)
C130.0233 (11)0.0254 (11)0.0377 (15)−0.0009 (10)0.0034 (11)0.0012 (10)
C140.0242 (11)0.0274 (11)0.0435 (15)0.0009 (10)0.0027 (12)0.0092 (11)
C150.0218 (11)0.0378 (13)0.0321 (14)0.0019 (10)−0.0002 (10)0.0134 (11)
C160.0179 (10)0.0328 (12)0.0230 (12)−0.0045 (10)−0.0004 (9)0.0038 (9)
C170.0478 (17)0.0537 (17)0.0253 (14)−0.0128 (15)−0.0092 (13)0.0070 (13)
B1—F31.382 (4)C5—H50.95
B1—F41.388 (4)C6—C71.509 (4)
B1—F21.392 (3)C7—H7A0.99
B1—F11.394 (3)C7—H7B0.99
O1—C161.363 (3)C8—C91.351 (3)
O1—C171.438 (3)C8—H80.95
N1—C101.325 (3)C9—H90.95
N1—C81.381 (3)C10—H100.95
N1—C71.482 (3)C11—C121.377 (3)
N2—C101.333 (3)C11—C161.406 (3)
N2—C91.387 (3)C12—C131.390 (3)
N2—C111.439 (3)C12—H120.95
C1—C21.383 (4)C13—C141.379 (4)
C1—C61.389 (4)C13—H130.95
C1—H10.95C14—C151.384 (4)
C2—C31.385 (4)C14—H140.95
C2—H20.95C15—C161.394 (3)
C3—C41.376 (5)C15—H150.95
C3—H30.95C17—H17A0.98
C4—C51.391 (5)C17—H17B0.98
C4—H40.95C17—H17C0.98
C5—C61.392 (4)
F3—B1—F4109.5 (2)C6—C7—H7B109.6
F3—B1—F2109.8 (3)H7A—C7—H7B108.1
F4—B1—F2109.6 (3)C9—C8—N1106.9 (2)
F3—B1—F1109.6 (3)C9—C8—H8126.5
F4—B1—F1109.4 (2)N1—C8—H8126.5
F2—B1—F1108.9 (2)C8—C9—N2107.1 (2)
C16—O1—C17117.6 (2)C8—C9—H9126.5
C10—N1—C8109.00 (19)N2—C9—H9126.5
C10—N1—C7124.7 (2)N1—C10—N2108.67 (19)
C8—N1—C7126.2 (2)N1—C10—H10125.7
C10—N2—C9108.33 (19)N2—C10—H10125.7
C10—N2—C11126.33 (19)C12—C11—C16121.0 (2)
C9—N2—C11125.33 (19)C12—C11—N2119.4 (2)
C2—C1—C6121.1 (2)C16—C11—N2119.7 (2)
C2—C1—H1119.5C11—C12—C13119.9 (2)
C6—C1—H1119.5C11—C12—H12120.0
C1—C2—C3119.6 (3)C13—C12—H12120.0
C1—C2—H2120.2C14—C13—C12119.6 (2)
C3—C2—H2120.2C14—C13—H13120.2
C4—C3—C2120.3 (3)C12—C13—H13120.2
C4—C3—H3119.8C13—C14—C15121.1 (2)
C2—C3—H3119.8C13—C14—H14119.5
C3—C4—C5120.0 (3)C15—C14—H14119.5
C3—C4—H4120.0C14—C15—C16120.1 (2)
C5—C4—H4120.0C14—C15—H15120.0
C4—C5—C6120.4 (3)C16—C15—H15120.0
C4—C5—H5119.8O1—C16—C15125.1 (2)
C6—C5—H5119.8O1—C16—C11116.4 (2)
C1—C6—C5118.7 (3)C15—C16—C11118.4 (2)
C1—C6—C7120.9 (2)O1—C17—H17A109.5
C5—C6—C7120.4 (2)O1—C17—H17B109.5
N1—C7—C6110.4 (2)H17A—C17—H17B109.5
N1—C7—H7A109.6O1—C17—H17C109.5
C6—C7—H7A109.6H17A—C17—H17C109.5
N1—C7—H7B109.6H17B—C17—H17C109.5
C6—C1—C2—C3−0.6 (4)C9—N2—C10—N10.1 (3)
C1—C2—C3—C40.5 (5)C11—N2—C10—N1−179.0 (2)
C2—C3—C4—C50.1 (5)C10—N2—C11—C12139.7 (2)
C3—C4—C5—C6−0.5 (5)C9—N2—C11—C12−39.2 (3)
C2—C1—C6—C50.2 (4)C10—N2—C11—C16−41.3 (3)
C2—C1—C6—C7−177.6 (2)C9—N2—C11—C16139.7 (2)
C4—C5—C6—C10.4 (4)C16—C11—C12—C130.8 (3)
C4—C5—C6—C7178.2 (3)N2—C11—C12—C13179.7 (2)
C10—N1—C7—C696.0 (3)C11—C12—C13—C140.6 (4)
C8—N1—C7—C6−79.3 (3)C12—C13—C14—C15−1.0 (4)
C1—C6—C7—N189.0 (3)C13—C14—C15—C160.0 (4)
C5—C6—C7—N1−88.8 (3)C17—O1—C16—C15−7.8 (4)
C10—N1—C8—C90.4 (3)C17—O1—C16—C11173.7 (2)
C7—N1—C8—C9176.3 (2)C14—C15—C16—O1−177.2 (2)
N1—C8—C9—N2−0.4 (3)C14—C15—C16—C111.4 (4)
C10—N2—C9—C80.2 (3)C12—C11—C16—O1176.9 (2)
C11—N2—C9—C8179.3 (2)N2—C11—C16—O1−2.0 (3)
C8—N1—C10—N2−0.3 (3)C12—C11—C16—C15−1.7 (3)
C7—N1—C10—N2−176.3 (2)N2—C11—C16—C15179.4 (2)
D—H···AD—HH···AD···AD—H···A
C7—H7B···F3i0.992.303.268 (3)167
C8—H8···F4i0.952.343.220 (3)154
C9—H9···F10.952.213.122 (3)161
C10—H10···F1ii0.952.373.236 (3)150
C10—H10···F2ii0.952.383.221 (3)147
C12—H12···O1ii0.952.573.292 (3)133
C14—H14···F3iii0.952.483.274 (3)140
C13—H13···Cg1ii0.942.613.460 (3)149
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C7—H7B⋯F3i0.992.303.268 (3)167
C8—H8⋯F4i0.952.343.220 (3)154
C9—H9⋯F10.952.213.122 (3)161
C10—H10⋯F1ii0.952.373.236 (3)150
C10—H10⋯F2ii0.952.383.221 (3)147
C12—H12⋯O1ii0.952.573.292 (3)133
C14—H14⋯F3iii0.952.483.274 (3)140
C13—H13⋯Cg1ii0.942.613.460 (3)149

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 ring.

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3.  Design, synthesis and in vitro antitumor activity of new trans 2-[2-(heteroaryl)vinyl]-1,3-dimethylimidazolium iodides.

Authors:  Francesco P Ballistreri; Vincenza Barresi; Paolo Benedetti; Gianluigi Caltabiano; Cosimo G Fortuna; Maria L Longo; Giuseppe Musumarra
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4.  Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts.

Authors:  D Demberelnyamba; Ki-Sub Kim; Sukjeong Choi; Seung-Yeob Park; Huen Lee; Chang-Jin Kim; Ick-Dong Yoo
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