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The structure of the title compound {systematic name: 1-[2-(2-naphthyl)-2-(propoxyimino)ethyl]-4,5-dihydroimidazol-3-iumchloride}, C
18H
20N
3O
+·Cl
−, is stabilized by intermolecular hydrogen bonds. The naphthalene moiety and the imidazole ring are essentially planar. The imidazole N2 atom is protonated and is connected to the Cl
− anion through a hydrogen bond [Cl
N2 = 3.004 (2) Å]. The configuration of the cation is
Z.
Supporting information
CCDC reference: 200775
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.032
- wR factor = 0.090
- Data-to-parameter ratio = 13.0
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
ABSTY_02 Alert C An _exptl_absorpt_correction_type has been given without
a literature citation. This should be contained in the
_exptl_absorpt_process_details field.
Absorption correction given as \y scan
REFLT_03
From the CIF: _diffrn_reflns_theta_max 26.22
From the CIF: _reflns_number_total 3216
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3446
Completeness (_total/calc) 93.33%
Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C18H20N3O+·Cl− | Z = 2 |
Mr = 329.82 | F(000) = 348 |
Triclinic, P1 | Dx = 1.277 Mg m−3 |
a = 8.6832 (16) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5662 (13) Å | Cell parameters from 25 reflections |
c = 11.3595 (16) Å | θ = 10.3–18.1° |
α = 104.967 (11)° | µ = 0.23 mm−1 |
β = 107.547 (13)° | T = 295 K |
γ = 94.120 (14)° | Prism, colorless |
V = 857.6 (2) Å3 | 0.46 × 0.42 × 0.24 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.007 |
non–profiled ω scans | θmax = 26.2°, θmin = 2.5° |
Absorption correction: ψ scan | h = 0→10 |
Tmin = 0.899, Tmax = 0.946 | k = −11→11 |
3444 measured reflections | l = −13→13 |
3216 independent reflections | 3 standard reflections every 120 min |
2561 reflections with I > 2σ(I) | intensity decay: −1% |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.0448P)2 + 0.1717P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.090 | (Δ/σ)max = 0.001 |
S = 1.02 | Δρmax = 0.24 e Å−3 |
3216 reflections | Δρmin = −0.15 e Å−3 |
248 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
H13 | 0.464 (3) | 0.734 (2) | 0.501 (2) | 0.085 (6)* | |
H15 | 0.730 (2) | 0.892 (2) | 0.3166 (18) | 0.078 (6)* | |
H14 | 0.419 (3) | 0.939 (2) | 0.231 (2) | 0.087 (7)* | |
H16A | 0.585 (2) | 0.545 (2) | 0.7555 (18) | 0.070 (6)* | |
H16B | 0.772 (3) | 0.615 (2) | 0.8292 (19) | 0.076 (6)* | |
H17B | 0.699 (3) | 0.853 (2) | 0.882 (2) | 0.085 (7)* | |
H17A | 0.507 (3) | 0.779 (2) | 0.810 (2) | 0.087 (7)* | |
H12A | 0.8700 (19) | 0.7741 (16) | 0.4639 (14) | 0.042 (4)* | |
H12B | 0.8198 (18) | 0.8204 (17) | 0.5931 (15) | 0.043 (4)* | |
H1' | 0.270 (3) | 0.839 (2) | 0.347 (2) | 0.089 (7)* | |
Cl1 | 0.03542 (4) | 0.86651 (4) | 0.31491 (4) | 0.04924 (13) | |
O1 | 0.67977 (15) | 0.67757 (13) | 0.67334 (11) | 0.0549 (3) | |
C8 | 0.79447 (17) | 0.48205 (16) | 0.40464 (15) | 0.0399 (3) | |
C11 | 0.76156 (17) | 0.59839 (16) | 0.50369 (14) | 0.0402 (3) | |
N1 | 0.63664 (14) | 0.79882 (13) | 0.42910 (12) | 0.0393 (3) | |
N2 | 0.38928 (17) | 0.83764 (16) | 0.36018 (14) | 0.0529 (3) | |
N3 | 0.71390 (16) | 0.55825 (14) | 0.58855 (13) | 0.0480 (3) | |
C9 | 0.83667 (18) | 0.39641 (16) | 0.19738 (15) | 0.0451 (4) | |
C1 | 0.80807 (19) | 0.50726 (16) | 0.29444 (15) | 0.0444 (4) | |
H1 | 0.7983 | 0.5995 | 0.2832 | 0.053* | |
C13 | 0.48917 (19) | 0.78010 (19) | 0.43954 (18) | 0.0505 (4) | |
C6 | 0.84008 (18) | 0.23286 (17) | 0.32994 (16) | 0.0472 (4) | |
H6 | 0.8512 | 0.1416 | 0.343 | 0.057* | |
C12 | 0.78670 (18) | 0.75646 (16) | 0.50430 (16) | 0.0404 (3) | |
C7 | 0.81339 (17) | 0.34116 (16) | 0.42218 (16) | 0.0442 (4) | |
H7 | 0.8074 | 0.3233 | 0.4975 | 0.053* | |
C10 | 0.85130 (18) | 0.25574 (16) | 0.21442 (16) | 0.0454 (4) | |
C15 | 0.6287 (2) | 0.8703 (2) | 0.3384 (2) | 0.0619 (5) | |
C2 | 0.8511 (2) | 0.4215 (2) | 0.08365 (17) | 0.0562 (4) | |
H2 | 0.8424 | 0.5135 | 0.0717 | 0.067* | |
C5 | 0.8798 (2) | 0.14553 (19) | 0.11682 (19) | 0.0591 (5) | |
H5 | 0.8903 | 0.0529 | 0.127 | 0.071* | |
C3 | 0.8777 (2) | 0.3124 (2) | −0.00879 (18) | 0.0623 (5) | |
H3 | 0.8863 | 0.3304 | −0.0834 | 0.075* | |
C16 | 0.6652 (2) | 0.6380 (2) | 0.78359 (17) | 0.0557 (4) | |
C4 | 0.8921 (2) | 0.1737 (2) | 0.00824 (19) | 0.0644 (5) | |
H4 | 0.9102 | 0.0999 | −0.0553 | 0.077* | |
C14 | 0.4743 (2) | 0.8949 (2) | 0.2963 (2) | 0.0694 (6) | |
C17 | 0.6183 (3) | 0.7669 (3) | 0.86421 (19) | 0.0641 (5) | |
C18 | 0.6084 (3) | 0.7459 (3) | 0.9896 (2) | 0.0893 (7) | |
H18A | 0.5784 | 0.8316 | 1.0374 | 0.134* | |
H18B | 0.713 | 0.7306 | 1.0399 | 0.134* | |
H18C | 0.5276 | 0.6621 | 0.971 | 0.134* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0385 (2) | 0.0534 (2) | 0.0655 (3) | 0.01445 (16) | 0.02465 (18) | 0.02299 (19) |
O1 | 0.0669 (8) | 0.0551 (7) | 0.0534 (7) | 0.0165 (6) | 0.0307 (6) | 0.0196 (5) |
C8 | 0.0311 (7) | 0.0397 (8) | 0.0492 (8) | 0.0075 (6) | 0.0115 (6) | 0.0156 (7) |
C11 | 0.0319 (7) | 0.0432 (8) | 0.0467 (8) | 0.0065 (6) | 0.0118 (6) | 0.0164 (7) |
N1 | 0.0348 (6) | 0.0389 (6) | 0.0484 (7) | 0.0087 (5) | 0.0174 (5) | 0.0151 (5) |
N2 | 0.0383 (7) | 0.0616 (9) | 0.0653 (9) | 0.0163 (6) | 0.0196 (7) | 0.0245 (7) |
N3 | 0.0488 (8) | 0.0474 (7) | 0.0519 (8) | 0.0113 (6) | 0.0205 (6) | 0.0159 (6) |
C9 | 0.0398 (8) | 0.0422 (8) | 0.0533 (9) | 0.0089 (6) | 0.0157 (7) | 0.0131 (7) |
C1 | 0.0448 (8) | 0.0376 (8) | 0.0545 (9) | 0.0108 (6) | 0.0173 (7) | 0.0173 (7) |
C13 | 0.0392 (9) | 0.0589 (10) | 0.0647 (10) | 0.0129 (7) | 0.0236 (8) | 0.0284 (9) |
C6 | 0.0380 (8) | 0.0371 (8) | 0.0659 (10) | 0.0074 (6) | 0.0126 (7) | 0.0191 (7) |
C12 | 0.0325 (7) | 0.0413 (8) | 0.0479 (9) | 0.0071 (6) | 0.0135 (7) | 0.0133 (7) |
C7 | 0.0335 (7) | 0.0453 (8) | 0.0568 (9) | 0.0057 (6) | 0.0136 (7) | 0.0221 (7) |
C10 | 0.0336 (8) | 0.0405 (8) | 0.0584 (10) | 0.0076 (6) | 0.0118 (7) | 0.0119 (7) |
C15 | 0.0488 (10) | 0.0809 (13) | 0.0786 (13) | 0.0196 (9) | 0.0301 (9) | 0.0485 (11) |
C2 | 0.0616 (11) | 0.0530 (10) | 0.0600 (10) | 0.0135 (8) | 0.0254 (9) | 0.0191 (8) |
C5 | 0.0527 (10) | 0.0455 (9) | 0.0746 (12) | 0.0133 (8) | 0.0215 (9) | 0.0082 (8) |
C3 | 0.0627 (11) | 0.0696 (12) | 0.0562 (11) | 0.0115 (9) | 0.0272 (9) | 0.0122 (9) |
C16 | 0.0574 (11) | 0.0648 (11) | 0.0498 (10) | 0.0086 (9) | 0.0210 (8) | 0.0214 (9) |
C4 | 0.0609 (11) | 0.0587 (11) | 0.0675 (12) | 0.0136 (9) | 0.0264 (10) | 0.0016 (9) |
C14 | 0.0568 (11) | 0.0902 (15) | 0.0826 (14) | 0.0277 (10) | 0.0256 (10) | 0.0542 (12) |
C17 | 0.0609 (12) | 0.0824 (14) | 0.0514 (10) | 0.0175 (11) | 0.0212 (9) | 0.0192 (10) |
C18 | 0.0885 (16) | 0.127 (2) | 0.0580 (12) | 0.0274 (15) | 0.0324 (12) | 0.0251 (13) |
Geometric parameters (Å, º) top
O1—N3 | 1.4040 (17) | C12—H12B | 0.977 (16) |
O1—C16 | 1.436 (2) | C7—H7 | 0.93 |
C8—C1 | 1.371 (2) | C10—C5 | 1.415 (2) |
C8—C7 | 1.426 (2) | C15—C14 | 1.341 (3) |
C8—C11 | 1.476 (2) | C15—H15 | 1.00 (2) |
C11—N3 | 1.2872 (19) | C2—C3 | 1.363 (2) |
C11—C12 | 1.510 (2) | C2—H2 | 0.93 |
N1—C13 | 1.3249 (19) | C5—C4 | 1.361 (3) |
N1—C15 | 1.365 (2) | C5—H5 | 0.93 |
N1—C12 | 1.4749 (19) | C3—C4 | 1.399 (3) |
N2—C13 | 1.312 (2) | C3—H3 | 0.93 |
N2—C14 | 1.357 (2) | C16—C17 | 1.496 (3) |
N2—H1' | 1.00 (2) | C16—H16A | 1.01 (2) |
C9—C2 | 1.413 (2) | C16—H16B | 0.98 (2) |
C9—C1 | 1.415 (2) | C4—H4 | 0.93 |
C9—C10 | 1.417 (2) | C14—H14 | 0.96 (2) |
C1—H1 | 0.93 | C17—C18 | 1.515 (3) |
C13—H13 | 0.99 (2) | C17—H17B | 0.98 (2) |
C6—C7 | 1.358 (2) | C17—H17A | 1.01 (2) |
C6—C10 | 1.415 (2) | C18—H18A | 0.96 |
C6—H6 | 0.93 | C18—H18B | 0.96 |
C12—H12A | 0.992 (16) | C18—H18C | 0.96 |
| | | |
N3—O1—C16 | 109.95 (12) | C6—C10—C9 | 118.31 (14) |
C1—C8—C7 | 118.72 (14) | C14—C15—N1 | 106.93 (16) |
C1—C8—C11 | 120.80 (13) | C14—C15—H15 | 134.3 (11) |
C7—C8—C11 | 120.48 (14) | N1—C15—H15 | 118.8 (11) |
N3—C11—C8 | 116.87 (13) | C3—C2—C9 | 120.83 (17) |
N3—C11—C12 | 122.76 (14) | C3—C2—H2 | 119.6 |
C8—C11—C12 | 120.37 (13) | C9—C2—H2 | 119.6 |
C13—N1—C15 | 108.00 (14) | C4—C5—C10 | 120.68 (17) |
C13—N1—C12 | 127.15 (13) | C4—C5—H5 | 119.7 |
C15—N1—C12 | 124.81 (13) | C10—C5—H5 | 119.7 |
C13—N2—C14 | 108.40 (15) | C2—C3—C4 | 120.22 (18) |
C13—N2—H1' | 126.8 (13) | C2—C3—H3 | 119.9 |
C14—N2—H1' | 124.8 (13) | C4—C3—H3 | 119.9 |
C11—N3—O1 | 111.29 (12) | O1—C16—C17 | 106.55 (15) |
C2—C9—C1 | 122.01 (14) | O1—C16—H16A | 110.5 (11) |
C2—C9—C10 | 118.84 (14) | C17—C16—H16A | 113.6 (11) |
C1—C9—C10 | 119.15 (14) | O1—C16—H16B | 107.7 (12) |
C8—C1—C9 | 121.63 (14) | C17—C16—H16B | 112.6 (12) |
C8—C1—H1 | 119.2 | H16A—C16—H16B | 105.7 (16) |
C9—C1—H1 | 119.2 | C5—C4—C3 | 120.66 (17) |
N2—C13—N1 | 109.10 (15) | C5—C4—H4 | 119.7 |
N2—C13—H13 | 127.0 (13) | C3—C4—H4 | 119.7 |
N1—C13—H13 | 123.8 (13) | C15—C14—N2 | 107.56 (17) |
C7—C6—C10 | 121.53 (14) | C15—C14—H14 | 132.3 (13) |
C7—C6—H6 | 119.2 | N2—C14—H14 | 120.1 (13) |
C10—C6—H6 | 119.2 | C16—C17—C18 | 113.02 (19) |
N1—C12—C11 | 112.42 (12) | C16—C17—H17B | 108.1 (13) |
N1—C12—H12A | 105.7 (9) | C18—C17—H17B | 110.0 (13) |
C11—C12—H12A | 110.9 (9) | C16—C17—H17A | 106.2 (13) |
N1—C12—H12B | 107.8 (9) | C18—C17—H17A | 109.6 (12) |
C11—C12—H12B | 109.4 (9) | H17B—C17—H17A | 109.8 (18) |
H12A—C12—H12B | 110.5 (13) | C17—C18—H18A | 109.5 |
C6—C7—C8 | 120.63 (15) | C17—C18—H18B | 109.5 |
C6—C7—H7 | 119.7 | H18A—C18—H18B | 109.5 |
C8—C7—H7 | 119.7 | C17—C18—H18C | 109.5 |
C5—C10—C6 | 122.92 (15) | H18A—C18—H18C | 109.5 |
C5—C10—C9 | 118.75 (16) | H18B—C18—H18C | 109.5 |
| | | |
C1—C8—C11—N3 | 164.63 (14) | C11—C8—C7—C6 | 178.53 (13) |
C7—C8—C11—N3 | −15.6 (2) | C7—C6—C10—C5 | 179.68 (15) |
C1—C8—C11—C12 | −16.4 (2) | C7—C6—C10—C9 | 1.0 (2) |
C7—C8—C11—C12 | 163.32 (13) | C2—C9—C10—C5 | 0.0 (2) |
C8—C11—N3—O1 | −177.33 (11) | C1—C9—C10—C5 | 179.96 (14) |
C12—C11—N3—O1 | 3.8 (2) | C2—C9—C10—C6 | 178.69 (15) |
C16—O1—N3—C11 | −166.33 (14) | C1—C9—C10—C6 | −1.3 (2) |
C7—C8—C1—C9 | 1.4 (2) | C13—N1—C15—C14 | 0.6 (2) |
C11—C8—C1—C9 | −178.85 (13) | C12—N1—C15—C14 | −177.25 (17) |
C2—C9—C1—C8 | −179.90 (15) | C1—C9—C2—C3 | −179.59 (16) |
C10—C9—C1—C8 | 0.1 (2) | C10—C9—C2—C3 | 0.4 (3) |
C14—N2—C13—N1 | 0.2 (2) | C6—C10—C5—C4 | −178.99 (16) |
C15—N1—C13—N2 | −0.5 (2) | C9—C10—C5—C4 | −0.4 (3) |
C12—N1—C13—N2 | 177.30 (14) | C9—C2—C3—C4 | −0.4 (3) |
C13—N1—C12—C11 | 51.4 (2) | N3—O1—C16—C17 | −176.39 (14) |
C15—N1—C12—C11 | −131.15 (17) | C10—C5—C4—C3 | 0.4 (3) |
N3—C11—C12—N1 | −89.44 (18) | C2—C3—C4—C5 | 0.0 (3) |
C8—C11—C12—N1 | 91.69 (16) | N1—C15—C14—N2 | −0.5 (2) |
C10—C6—C7—C8 | 0.5 (2) | C13—N2—C14—C15 | 0.2 (2) |
C1—C8—C7—C6 | −1.7 (2) | O1—C16—C17—C18 | −176.37 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1′···Cl1 | 0.99 (3) | 2.02 (3) | 3.004 (2) | 172.5 (17) |
C12—H12A···Cl1i | 0.99 (2) | 2.79 (2) | 3.748 (2) | 163.3 (13) |
C15—H15···Cl1i | 1.00 (3) | 2.69 (3) | 3.623 (2) | 155.5 (16) |
Symmetry code: (i) x+1, y, z. |
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