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In the title compound, C13H16N+·I, a weak C—H...I hydrogen bond is the main non-Coulombic inter­action between the cation and anion. Offset face-to-face π–π stacking occurs between quinolinium cations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806041225/ym2028sup1.cif
Contains datablocks Global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806041225/ym2028Isup2.hkl
Contains datablock I

CCDC reference: 628442

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.022
  • wR factor = 0.056
  • Data-to-parameter ratio = 23.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 I
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: Bruker SMART; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).

1-Butyl-quinolinium Iodide top
Crystal data top
C13H16N·IF(000) = 1232
Mr = 313.17Dx = 1.572 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 7461 reflections
a = 11.2807 (4) Åθ = 2.4–28.2°
b = 13.9968 (5) ŵ = 2.39 mm1
c = 16.7612 (6) ÅT = 295 K
V = 2646.49 (16) Å3Block, yellow
Z = 80.30 × 0.25 × 0.25 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3273 independent reflections
Radiation source: fine-focus sealed tube2563 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2005)
h = 915
Tmin = 0.456, Tmax = 0.550k = 1718
17852 measured reflectionsl = 2022
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022H-atom parameters constrained
wR(F2) = 0.056 w = 1/[σ2(Fo2) + (0.0227P)2 + 1.2579P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.002
3273 reflectionsΔρmax = 0.56 e Å3
138 parametersΔρmin = 0.53 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00435 (16)
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.

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 10.8818 (0.0016) x + 2.2825 (0.0069) y - 3.4708 (0.0112) z = 0.5747 (0.0069)

* -0.0512 (0.0017) N1 * -0.0001 (0.0019) C1 * 0.0418 (0.0020) C2 * 0.0130 (0.0020) C3 * -0.0328 (0.0020) C4 * -0.0087 (0.0022) C5 * 0.0345 (0.0021) C6 * 0.0269 (0.0020) C7 * -0.0092 (0.0019) C8 * -0.0141 (0.0020) C9

Rms deviation of fitted atoms = 0.0281

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.225397 (16)1.212518 (10)0.297207 (9)0.05776 (8)
N10.09157 (17)0.90771 (12)0.15899 (10)0.0489 (4)
C10.0718 (2)0.81567 (15)0.14577 (14)0.0535 (5)
H10.04940.77680.18820.064*
C20.0835 (2)0.77582 (15)0.07073 (15)0.0568 (6)
H20.06810.71120.06280.068*
C30.1175 (2)0.83141 (16)0.00892 (14)0.0566 (6)
H30.12810.80460.04140.068*
C40.1716 (2)0.99133 (18)0.04233 (14)0.0615 (6)
H40.18520.96630.09290.074*
C50.1852 (2)1.0864 (2)0.02936 (17)0.0693 (7)
H50.20801.12630.07100.083*
C60.1650 (2)1.12410 (17)0.04623 (17)0.0680 (7)
H60.17311.18960.05400.082*
C70.1339 (2)1.06805 (16)0.10929 (15)0.0577 (5)
H70.12181.09460.15950.069*
C80.12040 (18)0.96932 (14)0.09702 (12)0.0448 (4)
C90.13699 (19)0.93000 (15)0.02056 (12)0.0472 (5)
C100.0850 (2)0.94245 (17)0.24321 (13)0.0583 (6)
H10A0.14160.99390.25070.070*
H10B0.10650.89090.27900.070*
C110.0373 (2)0.97772 (19)0.26403 (15)0.0646 (6)
H11A0.09580.93040.24860.077*
H11B0.05391.03620.23500.077*
C120.0456 (3)0.9965 (2)0.35420 (16)0.0804 (8)
H12A0.02181.03480.37050.097*
H12B0.11681.03320.36490.097*
C130.0485 (3)0.9059 (3)0.4042 (2)0.1065 (12)
H13A0.10920.86400.38440.160*
H13B0.06500.92200.45880.160*
H13C0.02700.87440.40100.160*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.06868 (13)0.04900 (10)0.05560 (10)0.00344 (7)0.00379 (7)0.00602 (6)
N10.0540 (11)0.0472 (9)0.0455 (9)0.0029 (8)0.0006 (8)0.0004 (7)
C10.0533 (14)0.0467 (10)0.0606 (13)0.0012 (10)0.0020 (11)0.0080 (9)
C20.0604 (15)0.0433 (11)0.0667 (14)0.0024 (10)0.0013 (12)0.0031 (9)
C30.0592 (15)0.0559 (12)0.0546 (12)0.0092 (11)0.0029 (11)0.0088 (10)
C40.0537 (14)0.0748 (16)0.0559 (13)0.0032 (12)0.0063 (11)0.0135 (12)
C50.0554 (15)0.0726 (16)0.0799 (18)0.0057 (13)0.0003 (13)0.0311 (14)
C60.0584 (16)0.0490 (12)0.097 (2)0.0117 (11)0.0130 (14)0.0114 (13)
C70.0592 (14)0.0482 (11)0.0657 (14)0.0053 (10)0.0095 (11)0.0039 (10)
C80.0404 (11)0.0455 (10)0.0483 (11)0.0005 (8)0.0042 (9)0.0022 (8)
C90.0404 (11)0.0520 (11)0.0493 (11)0.0034 (9)0.0005 (9)0.0037 (9)
C100.0634 (16)0.0637 (13)0.0477 (12)0.0089 (12)0.0008 (10)0.0001 (10)
C110.0594 (16)0.0660 (14)0.0683 (16)0.0102 (12)0.0009 (12)0.0026 (12)
C120.075 (2)0.0860 (19)0.0800 (19)0.0006 (16)0.0241 (15)0.0242 (16)
C130.112 (3)0.132 (3)0.076 (2)0.008 (2)0.0312 (19)0.016 (2)
Geometric parameters (Å, º) top
N1—C11.326 (3)C7—C81.405 (3)
N1—C81.389 (3)C7—H70.9300
N1—C101.495 (3)C8—C91.407 (3)
C1—C21.382 (3)C10—C111.506 (3)
C1—H10.9300C10—H10A0.9700
C2—C31.351 (3)C10—H10B0.9700
C2—H20.9300C11—C121.537 (4)
C3—C91.411 (3)C11—H11A0.9700
C3—H30.9300C11—H11B0.9700
C4—C51.357 (4)C12—C131.520 (4)
C4—C91.414 (3)C12—H12A0.9700
C4—H40.9300C12—H12B0.9700
C5—C61.391 (4)C13—H13A0.9600
C5—H50.9300C13—H13B0.9600
C6—C71.362 (3)C13—H13C0.9600
C6—H60.9300
C1—N1—C8121.17 (18)C8—C9—C3119.19 (19)
C1—N1—C10117.74 (18)C8—C9—C4118.6 (2)
C8—N1—C10121.07 (17)C3—C9—C4122.3 (2)
N1—C1—C2121.9 (2)N1—C10—C11111.8 (2)
N1—C1—H1119.1N1—C10—H10A109.3
C2—C1—H1119.1C11—C10—H10A109.3
C3—C2—C1119.5 (2)N1—C10—H10B109.3
C3—C2—H2120.2C11—C10—H10B109.3
C1—C2—H2120.2H10A—C10—H10B107.9
C2—C3—C9120.1 (2)C10—C11—C12109.9 (2)
C2—C3—H3120.0C10—C11—H11A109.7
C9—C3—H3120.0C12—C11—H11A109.7
C5—C4—C9120.5 (2)C10—C11—H11B109.7
C5—C4—H4119.8C12—C11—H11B109.7
C9—C4—H4119.8H11A—C11—H11B108.2
C4—C5—C6119.9 (2)C13—C12—C11113.6 (2)
C4—C5—H5120.0C13—C12—H12A108.8
C6—C5—H5120.0C11—C12—H12A108.8
C7—C6—C5122.0 (2)C13—C12—H12B108.8
C7—C6—H6119.0C11—C12—H12B108.8
C5—C6—H6119.0H12A—C12—H12B107.7
C6—C7—C8118.7 (2)C12—C13—H13A109.5
C6—C7—H7120.6C12—C13—H13B109.5
C8—C7—H7120.6H13A—C13—H13B109.5
N1—C8—C7121.8 (2)C12—C13—H13C109.5
N1—C8—C9118.00 (17)H13A—C13—H13C109.5
C7—C8—C9120.2 (2)H13B—C13—H13C109.5
C8—N1—C1—C22.7 (4)N1—C8—C9—C33.4 (3)
C10—N1—C1—C2175.7 (2)C7—C8—C9—C3177.0 (2)
N1—C1—C2—C30.9 (4)N1—C8—C9—C4177.2 (2)
C1—C2—C3—C92.1 (4)C7—C8—C9—C42.3 (3)
C9—C4—C5—C60.0 (4)C2—C3—C9—C80.1 (3)
C4—C5—C6—C71.3 (4)C2—C3—C9—C4179.4 (2)
C5—C6—C7—C80.8 (4)C5—C4—C9—C81.8 (4)
C1—N1—C8—C7175.7 (2)C5—C4—C9—C3177.5 (2)
C10—N1—C8—C76.0 (3)C1—N1—C10—C1192.1 (3)
C1—N1—C8—C94.8 (3)C8—N1—C10—C1189.5 (3)
C10—N1—C8—C9173.56 (19)N1—C10—C11—C12170.4 (2)
C6—C7—C8—N1178.4 (2)C10—C11—C12—C1372.2 (3)
C6—C7—C8—C91.1 (3)
 

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