2-(2-Iodo-phen-yl)-1,2,3,4-tetra-hydro-isoquinoline-1-carbonitrile.

In the title compound, C(16)H(13)IN(2), the two benzene rings make a dihedral angle of 67.26 (5)°. The six-membered heterocycle of the tetra-hydro-isoquinoline unit adopts a half-chair conformation. In the crystal, adjacent mol-ecules are linked by pairs of weak inter-molecular C-H⋯N hydrogen bonds, forming inversion dimers. An intra-molecular C-H⋯I close contact is also observed.

Related literature

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

Crystal data

C16H13IN2

M = 360.18

Monoclinic,

a = 11.7607 (12) Å

b = 8.4473 (9) Å

c = 15.2601 (15) Å

β = 107.662 (1)°

V = 1444.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.20 mm−1

T = 296 K

0.42 × 0.32 × 0.26 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.458, T max = 0.598

10311 measured reflections

2689 independent reflections

2359 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.101

S = 1.02

2689 reflections

172 parameters

H-atom parameters constrained

Δρmax = 1.16 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015212/is2698sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015212/is2698Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811015212/is2698Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H13IN2	F(000) = 704
Mr = 360.18	Dx = 1.656 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5815 reflections
a = 11.7607 (12) Å	θ = 2.6–28.1°
b = 8.4473 (9) Å	µ = 2.20 mm−1
c = 15.2601 (15) Å	T = 296 K
β = 107.662 (1)°	Block, colourless
V = 1444.6 (3) Å3	0.42 × 0.32 × 0.26 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2689 independent reflections
Radiation source: fine-focus sealed tube	2359 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.458, Tmax = 0.598	k = −10→10
10311 measured reflections	l = −18→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0558P)2 + 2.5461P] where P = (Fo2 + 2Fc2)/3
2689 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 1.16 e Å−3
0 restraints	Δρmin = −0.51 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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.

	x	y	z	Uiso*/Ueq
C1	0.1617 (4)	1.1100 (5)	0.0837 (3)	0.0552 (10)
C2	0.0577 (4)	1.1981 (7)	0.0437 (5)	0.0757 (15)
H2	0.0056	1.2177	0.0778	0.091*
C3	0.0307 (5)	1.2559 (7)	−0.0439 (5)	0.0821 (17)
H3	−0.0380	1.3159	−0.0682	0.098*
C4	0.1052 (5)	1.2253 (7)	−0.0962 (4)	0.0785 (15)
H4	0.0867	1.2636	−0.1560	0.094*
C5	0.2082 (4)	1.1369 (6)	−0.0589 (3)	0.0612 (12)
H5	0.2594	1.1170	−0.0936	0.073*
C6	0.2349 (4)	1.0783 (5)	0.0296 (3)	0.0470 (9)
C7	0.3478 (4)	0.9792 (5)	0.0678 (3)	0.0412 (8)
H7	0.3501	0.9004	0.0213	0.049*
C8	0.3220 (4)	1.0020 (6)	0.2187 (3)	0.0535 (10)
H8A	0.3721	1.0956	0.2282	0.064*
H8B	0.3359	0.9488	0.2774	0.064*
C9	0.1920 (5)	1.0483 (6)	0.1804 (4)	0.0655 (13)
H9A	0.1426	0.9568	0.1815	0.079*
H9B	0.1740	1.1291	0.2194	0.079*
C10	0.4559 (4)	1.0835 (5)	0.0839 (3)	0.0457 (9)
C11	0.4559 (3)	0.7998 (4)	0.1851 (3)	0.0417 (8)
C12	0.4616 (4)	0.6511 (5)	0.1462 (3)	0.0440 (8)
C13	0.5645 (5)	0.5622 (5)	0.1734 (4)	0.0588 (11)
H13	0.5677	0.4651	0.1454	0.071*
C14	0.6628 (4)	0.6160 (6)	0.2419 (3)	0.0622 (12)
H14	0.7324	0.5559	0.2596	0.075*
C15	0.6579 (4)	0.7576 (6)	0.2839 (3)	0.0615 (11)
H15	0.7230	0.7923	0.3317	0.074*
C16	0.5558 (4)	0.8495 (5)	0.2549 (3)	0.0531 (10)
H16	0.5539	0.9469	0.2829	0.064*
I1	0.31094 (3)	0.55223 (3)	0.05008 (2)	0.05981 (15)
N1	0.3511 (3)	0.8951 (4)	0.1520 (2)	0.0425 (7)
N2	0.5385 (4)	1.1593 (5)	0.0987 (3)	0.0632 (10)

	U11	U22	U33	U12	U13	U23
C1	0.051 (2)	0.047 (2)	0.071 (3)	−0.0028 (19)	0.024 (2)	−0.013 (2)
C2	0.048 (3)	0.070 (3)	0.109 (4)	0.011 (2)	0.025 (3)	−0.021 (3)
C3	0.061 (3)	0.072 (4)	0.099 (4)	0.019 (3)	0.004 (3)	−0.011 (3)
C4	0.075 (3)	0.070 (3)	0.077 (3)	0.013 (3)	0.003 (3)	0.002 (3)
C5	0.060 (3)	0.060 (3)	0.061 (3)	0.005 (2)	0.014 (2)	−0.003 (2)
C6	0.043 (2)	0.038 (2)	0.059 (2)	−0.0019 (16)	0.0148 (18)	−0.0094 (18)
C7	0.0452 (19)	0.0354 (18)	0.047 (2)	−0.0025 (16)	0.0204 (16)	−0.0058 (16)
C8	0.069 (3)	0.049 (2)	0.051 (2)	0.000 (2)	0.031 (2)	−0.010 (2)
C9	0.065 (3)	0.066 (3)	0.082 (3)	0.008 (2)	0.046 (3)	−0.009 (2)
C10	0.046 (2)	0.042 (2)	0.054 (2)	0.0030 (18)	0.0218 (18)	0.0005 (17)
C11	0.051 (2)	0.0360 (19)	0.0430 (19)	−0.0035 (16)	0.0223 (17)	0.0000 (15)
C12	0.053 (2)	0.0389 (19)	0.046 (2)	−0.0035 (17)	0.0227 (17)	−0.0019 (16)
C13	0.073 (3)	0.042 (2)	0.067 (3)	0.008 (2)	0.030 (2)	0.001 (2)
C14	0.058 (3)	0.058 (3)	0.069 (3)	0.014 (2)	0.017 (2)	0.012 (2)
C15	0.057 (3)	0.066 (3)	0.056 (3)	−0.003 (2)	0.010 (2)	0.007 (2)
C16	0.062 (3)	0.048 (2)	0.050 (2)	−0.002 (2)	0.0191 (19)	−0.0051 (19)
I1	0.0717 (2)	0.0453 (2)	0.0607 (2)	−0.01053 (13)	0.01746 (16)	−0.01147 (12)
N1	0.0493 (18)	0.0375 (16)	0.0474 (17)	0.0006 (14)	0.0246 (15)	−0.0060 (14)
N2	0.058 (2)	0.054 (2)	0.082 (3)	−0.010 (2)	0.028 (2)	−0.004 (2)

C1—C6	1.387 (6)	C8—H8A	0.9700
C1—C2	1.403 (7)	C8—H8B	0.9700
C1—C9	1.503 (7)	C9—H9A	0.9700
C2—C3	1.368 (9)	C9—H9B	0.9700
C2—H2	0.9300	C10—N2	1.128 (5)
C3—C4	1.376 (9)	C11—C16	1.390 (6)
C3—H3	0.9300	C11—C12	1.400 (5)
C4—C5	1.390 (7)	C11—N1	1.430 (5)
C4—H4	0.9300	C12—C13	1.377 (6)
C5—C6	1.382 (6)	C12—I1	2.100 (4)
C5—H5	0.9300	C13—C14	1.380 (7)
C6—C7	1.528 (6)	C13—H13	0.9300
C7—N1	1.458 (5)	C14—C15	1.367 (7)
C7—C10	1.505 (6)	C14—H14	0.9300
C7—H7	0.9800	C15—C16	1.386 (7)
C8—N1	1.477 (5)	C15—H15	0.9300
C8—C9	1.513 (7)	C16—H16	0.9300
C6—C1—C2	117.4 (5)	H8A—C8—H8B	108.4
C6—C1—C9	120.8 (4)	C1—C9—C8	112.3 (4)
C2—C1—C9	121.7 (4)	C1—C9—H9A	109.1
C3—C2—C1	121.8 (5)	C8—C9—H9A	109.1
C3—C2—H2	119.1	C1—C9—H9B	109.1
C1—C2—H2	119.1	C8—C9—H9B	109.1
C2—C3—C4	120.0 (5)	H9A—C9—H9B	107.9
C2—C3—H3	120.0	N2—C10—C7	177.7 (5)
C4—C3—H3	120.0	C16—C11—C12	117.3 (4)
C3—C4—C5	119.5 (5)	C16—C11—N1	122.6 (3)
C3—C4—H4	120.3	C12—C11—N1	120.2 (3)
C5—C4—H4	120.3	C13—C12—C11	120.8 (4)
C6—C5—C4	120.3 (5)	C13—C12—I1	118.1 (3)
C6—C5—H5	119.9	C11—C12—I1	120.9 (3)
C4—C5—H5	119.9	C12—C13—C14	120.5 (4)
C5—C6—C1	121.0 (4)	C12—C13—H13	119.8
C5—C6—C7	118.8 (4)	C14—C13—H13	119.8
C1—C6—C7	120.2 (4)	C15—C14—C13	119.9 (4)
N1—C7—C10	110.3 (3)	C15—C14—H14	120.1
N1—C7—C6	113.0 (3)	C13—C14—H14	120.1
C10—C7—C6	109.6 (3)	C14—C15—C16	119.8 (4)
N1—C7—H7	107.9	C14—C15—H15	120.1
C10—C7—H7	107.9	C16—C15—H15	120.1
C6—C7—H7	107.9	C15—C16—C11	121.6 (4)
N1—C8—C9	108.0 (4)	C15—C16—H16	119.2
N1—C8—H8A	110.1	C11—C16—H16	119.2
C9—C8—H8A	110.1	C11—N1—C7	112.0 (3)
N1—C8—H8B	110.1	C11—N1—C8	117.1 (3)
C9—C8—H8B	110.1	C7—N1—C8	111.1 (3)
C6—C1—C2—C3	−2.3 (8)	C16—C11—C12—I1	173.5 (3)
C9—C1—C2—C3	179.2 (5)	N1—C11—C12—I1	−7.4 (5)
C1—C2—C3—C4	1.4 (9)	C11—C12—C13—C14	2.1 (7)
C2—C3—C4—C5	−0.6 (9)	I1—C12—C13—C14	−174.6 (4)
C3—C4—C5—C6	0.8 (8)	C12—C13—C14—C15	0.7 (7)
C4—C5—C6—C1	−1.8 (7)	C13—C14—C15—C16	−2.5 (7)
C4—C5—C6—C7	179.0 (4)	C14—C15—C16—C11	1.5 (7)
C2—C1—C6—C5	2.5 (7)	C12—C11—C16—C15	1.3 (6)
C9—C1—C6—C5	−179.0 (4)	N1—C11—C16—C15	−177.8 (4)
C2—C1—C6—C7	−178.3 (4)	C16—C11—N1—C7	98.6 (4)
C9—C1—C6—C7	0.2 (6)	C12—C11—N1—C7	−80.4 (4)
C5—C6—C7—N1	−166.6 (4)	C16—C11—N1—C8	−31.4 (5)
C1—C6—C7—N1	14.2 (5)	C12—C11—N1—C8	149.5 (4)
C5—C6—C7—C10	70.0 (5)	C10—C7—N1—C11	−58.6 (4)
C1—C6—C7—C10	−109.2 (4)	C6—C7—N1—C11	178.4 (3)
C6—C1—C9—C8	19.0 (6)	C10—C7—N1—C8	74.5 (4)
C2—C1—C9—C8	−162.6 (4)	C6—C7—N1—C8	−48.5 (4)
N1—C8—C9—C1	−51.5 (5)	C9—C8—N1—C11	−161.5 (4)
C16—C11—C12—C13	−3.1 (6)	C9—C8—N1—C7	68.1 (4)
N1—C11—C12—C13	176.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N2i	0.98	2.60	3.418 (5)	141
C7—H7···I1	0.98	3.03	3.633 (4)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯N2i	0.98	2.60	3.418 (5)	141
C7—H7⋯I1	0.98	3.03	3.633 (4)	121

Symmetry code: (i) .