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The structure of the title compound {systematic name: 1-[2-(2-naphthyl)-2-(propoxy­imino)­ethyl]-4,5-di­hydro­imidazol-3-iumchloride}, C18H20N3O+·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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802018962/cv6149sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802018962/cv6149Isup2.hkl
Contains datablock I

CCDC reference: 200775

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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


Yellow Alert 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

Computing details top

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).

(I) top
Crystal data top
C18H20N3O+·ClZ = 2
Mr = 329.82F(000) = 348
Triclinic, P1Dx = 1.277 Mg m3
a = 8.6832 (16) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.5662 (13) ÅCell parameters from 25 reflections
c = 11.3595 (16) Åθ = 10.3–18.1°
α = 104.967 (11)°µ = 0.23 mm1
β = 107.547 (13)°T = 295 K
γ = 94.120 (14)°Prism, colorless
V = 857.6 (2) Å30.46 × 0.42 × 0.24 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.007
non–profiled ω scansθmax = 26.2°, θmin = 2.5°
Absorption correction: ψ scanh = 010
Tmin = 0.899, Tmax = 0.946k = 1111
3444 measured reflectionsl = 1313
3216 independent reflections3 standard reflections every 120 min
2561 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH 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 = 1.02Δρmax = 0.24 e Å3
3216 reflectionsΔρmin = 0.15 e Å3
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
xyzUiso*/Ueq
H130.464 (3)0.734 (2)0.501 (2)0.085 (6)*
H150.730 (2)0.892 (2)0.3166 (18)0.078 (6)*
H140.419 (3)0.939 (2)0.231 (2)0.087 (7)*
H16A0.585 (2)0.545 (2)0.7555 (18)0.070 (6)*
H16B0.772 (3)0.615 (2)0.8292 (19)0.076 (6)*
H17B0.699 (3)0.853 (2)0.882 (2)0.085 (7)*
H17A0.507 (3)0.779 (2)0.810 (2)0.087 (7)*
H12A0.8700 (19)0.7741 (16)0.4639 (14)0.042 (4)*
H12B0.8198 (18)0.8204 (17)0.5931 (15)0.043 (4)*
H1'0.270 (3)0.839 (2)0.347 (2)0.089 (7)*
Cl10.03542 (4)0.86651 (4)0.31491 (4)0.04924 (13)
O10.67977 (15)0.67757 (13)0.67334 (11)0.0549 (3)
C80.79447 (17)0.48205 (16)0.40464 (15)0.0399 (3)
C110.76156 (17)0.59839 (16)0.50369 (14)0.0402 (3)
N10.63664 (14)0.79882 (13)0.42910 (12)0.0393 (3)
N20.38928 (17)0.83764 (16)0.36018 (14)0.0529 (3)
N30.71390 (16)0.55825 (14)0.58855 (13)0.0480 (3)
C90.83667 (18)0.39641 (16)0.19738 (15)0.0451 (4)
C10.80807 (19)0.50726 (16)0.29444 (15)0.0444 (4)
H10.79830.59950.28320.053*
C130.48917 (19)0.78010 (19)0.43954 (18)0.0505 (4)
C60.84008 (18)0.23286 (17)0.32994 (16)0.0472 (4)
H60.85120.14160.3430.057*
C120.78670 (18)0.75646 (16)0.50430 (16)0.0404 (3)
C70.81339 (17)0.34116 (16)0.42218 (16)0.0442 (4)
H70.80740.32330.49750.053*
C100.85130 (18)0.25574 (16)0.21442 (16)0.0454 (4)
C150.6287 (2)0.8703 (2)0.3384 (2)0.0619 (5)
C20.8511 (2)0.4215 (2)0.08365 (17)0.0562 (4)
H20.84240.51350.07170.067*
C50.8798 (2)0.14553 (19)0.11682 (19)0.0591 (5)
H50.89030.05290.1270.071*
C30.8777 (2)0.3124 (2)0.00879 (18)0.0623 (5)
H30.88630.33040.08340.075*
C160.6652 (2)0.6380 (2)0.78359 (17)0.0557 (4)
C40.8921 (2)0.1737 (2)0.00824 (19)0.0644 (5)
H40.91020.09990.05530.077*
C140.4743 (2)0.8949 (2)0.2963 (2)0.0694 (6)
C170.6183 (3)0.7669 (3)0.86421 (19)0.0641 (5)
C180.6084 (3)0.7459 (3)0.9896 (2)0.0893 (7)
H18A0.57840.83161.03740.134*
H18B0.7130.73061.03990.134*
H18C0.52760.66210.9710.134*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0385 (2)0.0534 (2)0.0655 (3)0.01445 (16)0.02465 (18)0.02299 (19)
O10.0669 (8)0.0551 (7)0.0534 (7)0.0165 (6)0.0307 (6)0.0196 (5)
C80.0311 (7)0.0397 (8)0.0492 (8)0.0075 (6)0.0115 (6)0.0156 (7)
C110.0319 (7)0.0432 (8)0.0467 (8)0.0065 (6)0.0118 (6)0.0164 (7)
N10.0348 (6)0.0389 (6)0.0484 (7)0.0087 (5)0.0174 (5)0.0151 (5)
N20.0383 (7)0.0616 (9)0.0653 (9)0.0163 (6)0.0196 (7)0.0245 (7)
N30.0488 (8)0.0474 (7)0.0519 (8)0.0113 (6)0.0205 (6)0.0159 (6)
C90.0398 (8)0.0422 (8)0.0533 (9)0.0089 (6)0.0157 (7)0.0131 (7)
C10.0448 (8)0.0376 (8)0.0545 (9)0.0108 (6)0.0173 (7)0.0173 (7)
C130.0392 (9)0.0589 (10)0.0647 (10)0.0129 (7)0.0236 (8)0.0284 (9)
C60.0380 (8)0.0371 (8)0.0659 (10)0.0074 (6)0.0126 (7)0.0191 (7)
C120.0325 (7)0.0413 (8)0.0479 (9)0.0071 (6)0.0135 (7)0.0133 (7)
C70.0335 (7)0.0453 (8)0.0568 (9)0.0057 (6)0.0136 (7)0.0221 (7)
C100.0336 (8)0.0405 (8)0.0584 (10)0.0076 (6)0.0118 (7)0.0119 (7)
C150.0488 (10)0.0809 (13)0.0786 (13)0.0196 (9)0.0301 (9)0.0485 (11)
C20.0616 (11)0.0530 (10)0.0600 (10)0.0135 (8)0.0254 (9)0.0191 (8)
C50.0527 (10)0.0455 (9)0.0746 (12)0.0133 (8)0.0215 (9)0.0082 (8)
C30.0627 (11)0.0696 (12)0.0562 (11)0.0115 (9)0.0272 (9)0.0122 (9)
C160.0574 (11)0.0648 (11)0.0498 (10)0.0086 (9)0.0210 (8)0.0214 (9)
C40.0609 (11)0.0587 (11)0.0675 (12)0.0136 (9)0.0264 (10)0.0016 (9)
C140.0568 (11)0.0902 (15)0.0826 (14)0.0277 (10)0.0256 (10)0.0542 (12)
C170.0609 (12)0.0824 (14)0.0514 (10)0.0175 (11)0.0212 (9)0.0192 (10)
C180.0885 (16)0.127 (2)0.0580 (12)0.0274 (15)0.0324 (12)0.0251 (13)
Geometric parameters (Å, º) top
O1—N31.4040 (17)C12—H12B0.977 (16)
O1—C161.436 (2)C7—H70.93
C8—C11.371 (2)C10—C51.415 (2)
C8—C71.426 (2)C15—C141.341 (3)
C8—C111.476 (2)C15—H151.00 (2)
C11—N31.2872 (19)C2—C31.363 (2)
C11—C121.510 (2)C2—H20.93
N1—C131.3249 (19)C5—C41.361 (3)
N1—C151.365 (2)C5—H50.93
N1—C121.4749 (19)C3—C41.399 (3)
N2—C131.312 (2)C3—H30.93
N2—C141.357 (2)C16—C171.496 (3)
N2—H1'1.00 (2)C16—H16A1.01 (2)
C9—C21.413 (2)C16—H16B0.98 (2)
C9—C11.415 (2)C4—H40.93
C9—C101.417 (2)C14—H140.96 (2)
C1—H10.93C17—C181.515 (3)
C13—H130.99 (2)C17—H17B0.98 (2)
C6—C71.358 (2)C17—H17A1.01 (2)
C6—C101.415 (2)C18—H18A0.96
C6—H60.93C18—H18B0.96
C12—H12A0.992 (16)C18—H18C0.96
N3—O1—C16109.95 (12)C6—C10—C9118.31 (14)
C1—C8—C7118.72 (14)C14—C15—N1106.93 (16)
C1—C8—C11120.80 (13)C14—C15—H15134.3 (11)
C7—C8—C11120.48 (14)N1—C15—H15118.8 (11)
N3—C11—C8116.87 (13)C3—C2—C9120.83 (17)
N3—C11—C12122.76 (14)C3—C2—H2119.6
C8—C11—C12120.37 (13)C9—C2—H2119.6
C13—N1—C15108.00 (14)C4—C5—C10120.68 (17)
C13—N1—C12127.15 (13)C4—C5—H5119.7
C15—N1—C12124.81 (13)C10—C5—H5119.7
C13—N2—C14108.40 (15)C2—C3—C4120.22 (18)
C13—N2—H1'126.8 (13)C2—C3—H3119.9
C14—N2—H1'124.8 (13)C4—C3—H3119.9
C11—N3—O1111.29 (12)O1—C16—C17106.55 (15)
C2—C9—C1122.01 (14)O1—C16—H16A110.5 (11)
C2—C9—C10118.84 (14)C17—C16—H16A113.6 (11)
C1—C9—C10119.15 (14)O1—C16—H16B107.7 (12)
C8—C1—C9121.63 (14)C17—C16—H16B112.6 (12)
C8—C1—H1119.2H16A—C16—H16B105.7 (16)
C9—C1—H1119.2C5—C4—C3120.66 (17)
N2—C13—N1109.10 (15)C5—C4—H4119.7
N2—C13—H13127.0 (13)C3—C4—H4119.7
N1—C13—H13123.8 (13)C15—C14—N2107.56 (17)
C7—C6—C10121.53 (14)C15—C14—H14132.3 (13)
C7—C6—H6119.2N2—C14—H14120.1 (13)
C10—C6—H6119.2C16—C17—C18113.02 (19)
N1—C12—C11112.42 (12)C16—C17—H17B108.1 (13)
N1—C12—H12A105.7 (9)C18—C17—H17B110.0 (13)
C11—C12—H12A110.9 (9)C16—C17—H17A106.2 (13)
N1—C12—H12B107.8 (9)C18—C17—H17A109.6 (12)
C11—C12—H12B109.4 (9)H17B—C17—H17A109.8 (18)
H12A—C12—H12B110.5 (13)C17—C18—H18A109.5
C6—C7—C8120.63 (15)C17—C18—H18B109.5
C6—C7—H7119.7H18A—C18—H18B109.5
C8—C7—H7119.7C17—C18—H18C109.5
C5—C10—C6122.92 (15)H18A—C18—H18C109.5
C5—C10—C9118.75 (16)H18B—C18—H18C109.5
C1—C8—C11—N3164.63 (14)C11—C8—C7—C6178.53 (13)
C7—C8—C11—N315.6 (2)C7—C6—C10—C5179.68 (15)
C1—C8—C11—C1216.4 (2)C7—C6—C10—C91.0 (2)
C7—C8—C11—C12163.32 (13)C2—C9—C10—C50.0 (2)
C8—C11—N3—O1177.33 (11)C1—C9—C10—C5179.96 (14)
C12—C11—N3—O13.8 (2)C2—C9—C10—C6178.69 (15)
C16—O1—N3—C11166.33 (14)C1—C9—C10—C61.3 (2)
C7—C8—C1—C91.4 (2)C13—N1—C15—C140.6 (2)
C11—C8—C1—C9178.85 (13)C12—N1—C15—C14177.25 (17)
C2—C9—C1—C8179.90 (15)C1—C9—C2—C3179.59 (16)
C10—C9—C1—C80.1 (2)C10—C9—C2—C30.4 (3)
C14—N2—C13—N10.2 (2)C6—C10—C5—C4178.99 (16)
C15—N1—C13—N20.5 (2)C9—C10—C5—C40.4 (3)
C12—N1—C13—N2177.30 (14)C9—C2—C3—C40.4 (3)
C13—N1—C12—C1151.4 (2)N3—O1—C16—C17176.39 (14)
C15—N1—C12—C11131.15 (17)C10—C5—C4—C30.4 (3)
N3—C11—C12—N189.44 (18)C2—C3—C4—C50.0 (3)
C8—C11—C12—N191.69 (16)N1—C15—C14—N20.5 (2)
C10—C6—C7—C80.5 (2)C13—N2—C14—C150.2 (2)
C1—C8—C7—C61.7 (2)O1—C16—C17—C18176.37 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···Cl10.99 (3)2.02 (3)3.004 (2)172.5 (17)
C12—H12A···Cl1i0.99 (2)2.79 (2)3.748 (2)163.3 (13)
C15—H15···Cl1i1.00 (3)2.69 (3)3.623 (2)155.5 (16)
Symmetry code: (i) x+1, y, z.
 

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