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Acta Cryst. (2011). E67, o2072    [ doi:10.1107/S1600536811019830 ]

2-(4-Iodophenyl)-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile

Y. Ma, L. Du, Q. Zhang, F. Cao and L. Zhou

Abstract top

In the title compound, C16H13IN2, the benzene ring of the tetrahydroisoquinoline moiety makes a dihedral angle of 45.02 (9)° with the benzene ring of the 4-iodophenyl fragment. The N atom and the adjacent unsubstituted C atom of the tetrahydroisoquinoline unit are displaced by 0.294 (2) and 0.441 (3) Å, respectively, from the plane through the remaining eight C atoms. In the crystal, pairs of adjacent molecules are linked into dimers by weak intermolecular C-H...[pi] interactions.

Comment top

The tetrahydroisoquinoline derivatives have attracted great attention in recent years due to their neurotoxicity (Abe et al. 2005; Storch et al. 2002), antitumor activities (Lane et al. 2006; Wright et al. 1990), and antimicrobial activity (Kamal et al. 2011; Liu et al. 2009). We report here the synthesis and crystal structure of the title compound.

As shown in Fig. 1, benzene ring C1/C2/C3/C4/C5/C6 make a dihedral angle of 45.02 (9)° with benzene ring C11/C12/C13/C14/C15/C16. Atoms C7 and C9 are coplanar with benzene ring of the tetrahydroisoquinoline moiety. The conformation of the saturated six membered ring of the tetrahydroisoquinoline fragment is analyzed with respect to the plane formed by C1/C2/C3/C4/C5/C6/C7/C9, and the corresponding deviations are 0.441 (3) and 0.294 (2) Å for C8 and N1, respectively.

In the crystal structure, two adjacent molecules are linked into a dimer by weak intermolecular C—H···π interactions. The H···Cg distance is 2.930 Å with C···Cg of 3.449 (4) Å and C—H···Cg angle of 117°, as shown in Fig. 2. However, there are no weak C—H···I hydrogen bonds in the crystal structure of the title compound.

Related literature top

For the synthesis of the title compound, see: Ishii et al. (1985). For the biological activity of tetrahydroisoquinoline derivatives, see: Abe et al. (2005); Kamal et al. (2011); Lane et al. (2006); Liu et al. (2009); Storch et al. (2002); Wright et al. (1990).

Experimental top

The title compound was synthesized according to the literature procedure (Ishii, et al. 1985), and crystals were obtained from a solution in ethyl acetate by slow evaporation at room temperature.

Refinement top

All of the non-hydrogen atoms were refined anisotropically. The hydrogen atoms were assigned with isotropic displacement factors Uiso(H) = 1.2 times Ueq(C), and included in the final refinement by using geometrical constraints, with C—H distances of 0.93 Å.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular of the title compound showing 30% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme.
[Figure 2] Fig. 2. The dimer structure of the title compound showing C—H···π interactions.
2-(4-Iodophenyl)-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile top
Crystal data top
C16H13IN2F(000) = 704
Mr = 360.18Dx = 1.696 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4624 reflections
a = 7.347 (4) Åθ = 2.8–26.3°
b = 14.832 (8) ŵ = 2.26 mm−1
c = 13.149 (7) ÅT = 296 K
β = 100.157 (6)°Block, colourless
V = 1410.5 (13) Å30.32 × 0.17 × 0.15 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2604 independent reflections
Radiation source: fine-focus sealed tube2185 reflections with I > 2σ(I)
graphiteRint = 0.018
φ and ω scansθmax = 25.5°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −8→8
Tmin = 0.532, Tmax = 0.728k = −17→17
10475 measured reflectionsl = −15→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0295P)2 + 0.8261P]
where P = (Fo2 + 2Fc2)/3
2604 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.55 e Å−3
0 restraintsΔρmin = −0.42 e Å−3
Crystal data top
C16H13IN2V = 1410.5 (13) Å3
Mr = 360.18Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.347 (4) ŵ = 2.26 mm−1
b = 14.832 (8) ÅT = 296 K
c = 13.149 (7) Å0.32 × 0.17 × 0.15 mm
β = 100.157 (6)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2604 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2185 reflections with I > 2σ(I)
Tmin = 0.532, Tmax = 0.728Rint = 0.018
10475 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.062Δρmax = 0.55 e Å−3
S = 1.00Δρmin = −0.42 e Å−3
2604 reflectionsAbsolute structure: ?
172 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2714 (3)−0.15209 (17)0.6261 (2)0.0437 (6)
C20.3306 (4)−0.21738 (19)0.5630 (2)0.0546 (7)
H20.3822−0.20010.50640.065*
C30.3126 (4)−0.3078 (2)0.5845 (3)0.0669 (8)
H30.3516−0.35110.54200.080*
C40.2371 (4)−0.3340 (2)0.6686 (3)0.0689 (9)
H40.2256−0.39490.68320.083*
C50.1793 (4)−0.2698 (2)0.7306 (2)0.0600 (8)
H50.1289−0.28790.78740.072*
C60.1940 (4)−0.17800 (19)0.7107 (2)0.0478 (6)
C70.1195 (4)−0.1080 (2)0.7750 (2)0.0573 (7)
H7A−0.0136−0.10430.75380.069*
H7B0.1448−0.12650.84680.069*
C80.2025 (4)−0.01582 (19)0.76536 (19)0.0488 (6)
H8A0.13750.02870.79950.059*
H8B0.3314−0.01580.79850.059*
C90.2960 (3)−0.05317 (17)0.60181 (19)0.0413 (6)
H90.2557−0.04460.52730.050*
C100.4980 (4)−0.02988 (18)0.6277 (2)0.0467 (6)
C110.2096 (3)0.10006 (16)0.63235 (19)0.0393 (5)
C120.1592 (4)0.12960 (18)0.53047 (19)0.0448 (6)
H120.11360.08830.47900.054*
C130.1760 (4)0.21893 (18)0.5050 (2)0.0485 (6)
H130.14210.23770.43680.058*
C140.2433 (3)0.28069 (17)0.5812 (2)0.0446 (6)
C150.2939 (4)0.2529 (2)0.6825 (2)0.0523 (6)
H150.33880.29450.73370.063*
C160.2777 (4)0.16344 (18)0.7076 (2)0.0495 (6)
H160.31280.14510.77590.059*
I10.26329 (3)0.417129 (13)0.542901 (16)0.06623 (10)
N10.1875 (3)0.00726 (14)0.65543 (15)0.0412 (5)
N20.6490 (4)−0.01027 (19)0.6491 (2)0.0653 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0390 (13)0.0450 (14)0.0460 (14)0.0045 (11)0.0048 (11)0.0015 (11)
C20.0525 (16)0.0515 (16)0.0595 (17)0.0038 (13)0.0094 (13)−0.0053 (13)
C30.0638 (19)0.0478 (17)0.087 (2)0.0097 (15)0.0064 (17)−0.0124 (16)
C40.065 (2)0.0480 (18)0.088 (2)0.0024 (15)−0.0024 (18)0.0113 (17)
C50.0554 (17)0.0551 (18)0.0669 (19)−0.0026 (14)0.0036 (14)0.0177 (15)
C60.0408 (14)0.0522 (15)0.0484 (15)0.0000 (12)0.0024 (11)0.0063 (12)
C70.0628 (18)0.0627 (18)0.0506 (16)0.0028 (14)0.0217 (14)0.0126 (13)
C80.0569 (16)0.0543 (16)0.0377 (13)0.0071 (13)0.0150 (12)0.0013 (12)
C90.0431 (14)0.0449 (13)0.0363 (13)0.0030 (11)0.0085 (10)−0.0005 (10)
C100.0496 (17)0.0475 (15)0.0465 (15)0.0045 (12)0.0182 (12)0.0000 (12)
C110.0343 (13)0.0451 (14)0.0391 (13)0.0060 (10)0.0078 (10)−0.0017 (10)
C120.0452 (15)0.0470 (15)0.0392 (13)0.0040 (12)−0.0012 (11)−0.0036 (11)
C130.0531 (16)0.0501 (15)0.0397 (13)0.0061 (12)0.0015 (12)0.0038 (12)
C140.0436 (14)0.0405 (13)0.0501 (15)0.0037 (11)0.0095 (11)0.0003 (11)
C150.0573 (16)0.0515 (16)0.0456 (14)−0.0012 (13)0.0023 (12)−0.0090 (12)
C160.0570 (16)0.0519 (16)0.0364 (13)0.0039 (13)−0.0004 (12)0.0000 (12)
I10.09151 (18)0.04555 (13)0.06353 (15)−0.00255 (10)0.01885 (11)0.00301 (9)
N10.0436 (11)0.0441 (12)0.0374 (11)0.0057 (9)0.0114 (9)0.0007 (9)
N20.0508 (16)0.0792 (19)0.0693 (17)−0.0032 (14)0.0199 (13)−0.0087 (14)
Geometric parameters (Å, °) top
C1—C61.391 (4)C8—H8B0.9700
C1—C21.393 (4)C9—N11.461 (3)
C1—C91.519 (4)C9—C101.503 (4)
C2—C31.381 (4)C9—H90.9800
C2—H20.9300C10—N21.133 (3)
C3—C41.378 (5)C11—C161.392 (4)
C3—H30.9300C11—C121.396 (3)
C4—C51.368 (5)C11—N11.425 (3)
C4—H40.9300C12—C131.378 (4)
C5—C61.395 (4)C12—H120.9300
C5—H50.9300C13—C141.383 (4)
C6—C71.501 (4)C13—H130.9300
C7—C81.511 (4)C14—C151.381 (4)
C7—H7A0.9700C14—I12.097 (3)
C7—H7B0.9700C15—C161.378 (4)
C8—N11.471 (3)C15—H150.9300
C8—H8A0.9700C16—H160.9300
C6—C1—C2119.9 (3)H8A—C8—H8B108.3
C6—C1—C9121.0 (2)N1—C9—C10110.6 (2)
C2—C1—C9119.0 (2)N1—C9—C1113.3 (2)
C3—C2—C1120.1 (3)C10—C9—C1108.9 (2)
C3—C2—H2119.9N1—C9—H9108.0
C1—C2—H2119.9C10—C9—H9108.0
C2—C3—C4120.3 (3)C1—C9—H9108.0
C2—C3—H3119.8N2—C10—C9177.9 (3)
C4—C3—H3119.8C16—C11—C12118.1 (2)
C5—C4—C3119.5 (3)C16—C11—N1122.8 (2)
C5—C4—H4120.2C12—C11—N1119.1 (2)
C3—C4—H4120.2C13—C12—C11121.0 (2)
C4—C5—C6121.7 (3)C13—C12—H12119.5
C4—C5—H5119.2C11—C12—H12119.5
C6—C5—H5119.2C12—C13—C14119.8 (2)
C1—C6—C5118.4 (3)C12—C13—H13120.1
C1—C6—C7120.0 (2)C14—C13—H13120.1
C5—C6—C7121.5 (3)C13—C14—C15120.1 (2)
C8—C7—C6112.7 (2)C13—C14—I1119.8 (2)
C8—C7—H7A109.1C15—C14—I1120.1 (2)
C6—C7—H7A109.0C16—C15—C14119.9 (2)
C8—C7—H7B109.0C16—C15—H15120.0
C6—C7—H7B109.1C14—C15—H15120.0
H7A—C7—H7B107.8C15—C16—C11121.0 (2)
N1—C8—C7109.4 (2)C15—C16—H16119.5
N1—C8—H8A109.8C11—C16—H16119.5
C7—C8—H8A109.8C11—N1—C9113.42 (19)
N1—C8—H8B109.8C11—N1—C8116.3 (2)
C7—C8—H8B109.8C9—N1—C8112.3 (2)
C6—C1—C2—C3−0.1 (4)N1—C11—C12—C13179.1 (2)
C9—C1—C2—C3178.9 (3)C11—C12—C13—C14−0.1 (4)
C1—C2—C3—C4−0.4 (5)C12—C13—C14—C150.1 (4)
C2—C3—C4—C50.3 (5)C12—C13—C14—I1−178.6 (2)
C3—C4—C5—C60.2 (5)C13—C14—C15—C160.2 (4)
C2—C1—C6—C50.5 (4)I1—C14—C15—C16178.9 (2)
C9—C1—C6—C5−178.4 (2)C14—C15—C16—C11−0.5 (4)
C2—C1—C6—C7−176.2 (3)C12—C11—C16—C150.4 (4)
C9—C1—C6—C74.8 (4)N1—C11—C16—C15−178.8 (2)
C4—C5—C6—C1−0.6 (4)C16—C11—N1—C9−119.8 (3)
C4—C5—C6—C7176.1 (3)C12—C11—N1—C961.0 (3)
C1—C6—C7—C8−22.5 (4)C16—C11—N1—C812.6 (3)
C5—C6—C7—C8160.9 (3)C12—C11—N1—C8−166.6 (2)
C6—C7—C8—N150.9 (3)C10—C9—N1—C1157.7 (3)
C6—C1—C9—N1−16.1 (3)C1—C9—N1—C11−179.7 (2)
C2—C1—C9—N1165.0 (2)C10—C9—N1—C8−76.6 (3)
C6—C1—C9—C10107.4 (3)C1—C9—N1—C846.0 (3)
C2—C1—C9—C10−71.5 (3)C7—C8—N1—C11162.7 (2)
C16—C11—C12—C13−0.1 (4)C7—C8—N1—C9−64.4 (3)
Hydrogen-bond geometry (Å, °) top
Cg is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C13—H13···Cgi0.932.933.449 (4)117
Symmetry codes: (i) −x, −y, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
Cg is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C13—H13···Cgi0.932.933.449 (4)117
Symmetry codes: (i) −x, −y, −z+1.
Acknowledgements top

This work was supported by National Natural Science Foundation of China (NNSF; No. 30771454; 31000865).

references
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