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

In the title compound, C(16)H(13)IN(2), the benzene ring of the tetra-hydro-isoquinoline moiety makes a dihedral angle of 45.02 (9)° with the benzene ring of the 4-iodo-phenyl fragment. The N atom and the adjacent unsubstituted C atom of the tetra-hydro-isoquinoline 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 mol-ecules are linked into dimers by weak inter-molecular C-H⋯π inter-actions.

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 = 7.347 (4) Å

b = 14.832 (8) Å

c = 13.149 (7) Å

β = 100.157 (6)°

V = 1410.5 (13) Å3

Z = 4

Mo Kα radiation

μ = 2.26 mm−1

T = 296 K

0.32 × 0.17 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.532, T max = 0.728

10475 measured reflections

2604 independent reflections

2185 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.062

S = 1.00

2604 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; 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 datablock(s) global, I. DOI: 10.1107/S1600536811019830/rn2087sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019830/rn2087Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019830/rn2087Isup3.cml

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

C16H13IN2	F(000) = 704
Mr = 360.18	Dx = 1.696 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4624 reflections
a = 7.347 (4) Å	θ = 2.8–26.3°
b = 14.832 (8) Å	µ = 2.26 mm−1
c = 13.149 (7) Å	T = 296 K
β = 100.157 (6)°	Block, colourless
V = 1410.5 (13) Å3	0.32 × 0.17 × 0.15 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2604 independent reflections
Radiation source: fine-focus sealed tube	2185 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 25.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.532, Tmax = 0.728	k = −17→17
10475 measured reflections	l = −15→15

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062	H-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 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.42 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	0.2714 (3)	−0.15209 (17)	0.6261 (2)	0.0437 (6)
C2	0.3306 (4)	−0.21738 (19)	0.5630 (2)	0.0546 (7)
H2	0.3822	−0.2001	0.5064	0.065*
C3	0.3126 (4)	−0.3078 (2)	0.5845 (3)	0.0669 (8)
H3	0.3516	−0.3511	0.5420	0.080*
C4	0.2371 (4)	−0.3340 (2)	0.6686 (3)	0.0689 (9)
H4	0.2256	−0.3949	0.6832	0.083*
C5	0.1793 (4)	−0.2698 (2)	0.7306 (2)	0.0600 (8)
H5	0.1289	−0.2879	0.7874	0.072*
C6	0.1940 (4)	−0.17800 (19)	0.7107 (2)	0.0478 (6)
C7	0.1195 (4)	−0.1080 (2)	0.7750 (2)	0.0573 (7)
H7A	−0.0136	−0.1043	0.7538	0.069*
H7B	0.1448	−0.1265	0.8468	0.069*
C8	0.2025 (4)	−0.01582 (19)	0.76536 (19)	0.0488 (6)
H8A	0.1375	0.0287	0.7995	0.059*
H8B	0.3314	−0.0158	0.7985	0.059*
C9	0.2960 (3)	−0.05317 (17)	0.60181 (19)	0.0413 (6)
H9	0.2557	−0.0446	0.5273	0.050*
C10	0.4980 (4)	−0.02988 (18)	0.6277 (2)	0.0467 (6)
C11	0.2096 (3)	0.10006 (16)	0.63235 (19)	0.0393 (5)
C12	0.1592 (4)	0.12960 (18)	0.53047 (19)	0.0448 (6)
H12	0.1136	0.0883	0.4790	0.054*
C13	0.1760 (4)	0.21893 (18)	0.5050 (2)	0.0485 (6)
H13	0.1421	0.2377	0.4368	0.058*
C14	0.2433 (3)	0.28069 (17)	0.5812 (2)	0.0446 (6)
C15	0.2939 (4)	0.2529 (2)	0.6825 (2)	0.0523 (6)
H15	0.3388	0.2945	0.7337	0.063*
C16	0.2777 (4)	0.16344 (18)	0.7076 (2)	0.0495 (6)
H16	0.3128	0.1451	0.7759	0.059*
I1	0.26329 (3)	0.417129 (13)	0.542901 (16)	0.06623 (10)
N1	0.1875 (3)	0.00726 (14)	0.65543 (15)	0.0412 (5)
N2	0.6490 (4)	−0.01027 (19)	0.6491 (2)	0.0653 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0390 (13)	0.0450 (14)	0.0460 (14)	0.0045 (11)	0.0048 (11)	0.0015 (11)
C2	0.0525 (16)	0.0515 (16)	0.0595 (17)	0.0038 (13)	0.0094 (13)	−0.0053 (13)
C3	0.0638 (19)	0.0478 (17)	0.087 (2)	0.0097 (15)	0.0064 (17)	−0.0124 (16)
C4	0.065 (2)	0.0480 (18)	0.088 (2)	0.0024 (15)	−0.0024 (18)	0.0113 (17)
C5	0.0554 (17)	0.0551 (18)	0.0669 (19)	−0.0026 (14)	0.0036 (14)	0.0177 (15)
C6	0.0408 (14)	0.0522 (15)	0.0484 (15)	0.0000 (12)	0.0024 (11)	0.0063 (12)
C7	0.0628 (18)	0.0627 (18)	0.0506 (16)	0.0028 (14)	0.0217 (14)	0.0126 (13)
C8	0.0569 (16)	0.0543 (16)	0.0377 (13)	0.0071 (13)	0.0150 (12)	0.0013 (12)
C9	0.0431 (14)	0.0449 (13)	0.0363 (13)	0.0030 (11)	0.0085 (10)	−0.0005 (10)
C10	0.0496 (17)	0.0475 (15)	0.0465 (15)	0.0045 (12)	0.0182 (12)	0.0000 (12)
C11	0.0343 (13)	0.0451 (14)	0.0391 (13)	0.0060 (10)	0.0078 (10)	−0.0017 (10)
C12	0.0452 (15)	0.0470 (15)	0.0392 (13)	0.0040 (12)	−0.0012 (11)	−0.0036 (11)
C13	0.0531 (16)	0.0501 (15)	0.0397 (13)	0.0061 (12)	0.0015 (12)	0.0038 (12)
C14	0.0436 (14)	0.0405 (13)	0.0501 (15)	0.0037 (11)	0.0095 (11)	0.0003 (11)
C15	0.0573 (16)	0.0515 (16)	0.0456 (14)	−0.0012 (13)	0.0023 (12)	−0.0090 (12)
C16	0.0570 (16)	0.0519 (16)	0.0364 (13)	0.0039 (13)	−0.0004 (12)	0.0000 (12)
I1	0.09151 (18)	0.04555 (13)	0.06353 (15)	−0.00255 (10)	0.01885 (11)	0.00301 (9)
N1	0.0436 (11)	0.0441 (12)	0.0374 (11)	0.0057 (9)	0.0114 (9)	0.0007 (9)
N2	0.0508 (16)	0.0792 (19)	0.0693 (17)	−0.0032 (14)	0.0199 (13)	−0.0087 (14)

C1—C6	1.391 (4)	C8—H8B	0.9700
C1—C2	1.393 (4)	C9—N1	1.461 (3)
C1—C9	1.519 (4)	C9—C10	1.503 (4)
C2—C3	1.381 (4)	C9—H9	0.9800
C2—H2	0.9300	C10—N2	1.133 (3)
C3—C4	1.378 (5)	C11—C16	1.392 (4)
C3—H3	0.9300	C11—C12	1.396 (3)
C4—C5	1.368 (5)	C11—N1	1.425 (3)
C4—H4	0.9300	C12—C13	1.378 (4)
C5—C6	1.395 (4)	C12—H12	0.9300
C5—H5	0.9300	C13—C14	1.383 (4)
C6—C7	1.501 (4)	C13—H13	0.9300
C7—C8	1.511 (4)	C14—C15	1.381 (4)
C7—H7A	0.9700	C14—I1	2.097 (3)
C7—H7B	0.9700	C15—C16	1.378 (4)
C8—N1	1.471 (3)	C15—H15	0.9300
C8—H8A	0.9700	C16—H16	0.9300
C6—C1—C2	119.9 (3)	H8A—C8—H8B	108.3
C6—C1—C9	121.0 (2)	N1—C9—C10	110.6 (2)
C2—C1—C9	119.0 (2)	N1—C9—C1	113.3 (2)
C3—C2—C1	120.1 (3)	C10—C9—C1	108.9 (2)
C3—C2—H2	119.9	N1—C9—H9	108.0
C1—C2—H2	119.9	C10—C9—H9	108.0
C2—C3—C4	120.3 (3)	C1—C9—H9	108.0
C2—C3—H3	119.8	N2—C10—C9	177.9 (3)
C4—C3—H3	119.8	C16—C11—C12	118.1 (2)
C5—C4—C3	119.5 (3)	C16—C11—N1	122.8 (2)
C5—C4—H4	120.2	C12—C11—N1	119.1 (2)
C3—C4—H4	120.2	C13—C12—C11	121.0 (2)
C4—C5—C6	121.7 (3)	C13—C12—H12	119.5
C4—C5—H5	119.2	C11—C12—H12	119.5
C6—C5—H5	119.2	C12—C13—C14	119.8 (2)
C1—C6—C5	118.4 (3)	C12—C13—H13	120.1
C1—C6—C7	120.0 (2)	C14—C13—H13	120.1
C5—C6—C7	121.5 (3)	C13—C14—C15	120.1 (2)
C8—C7—C6	112.7 (2)	C13—C14—I1	119.8 (2)
C8—C7—H7A	109.1	C15—C14—I1	120.1 (2)
C6—C7—H7A	109.0	C16—C15—C14	119.9 (2)
C8—C7—H7B	109.0	C16—C15—H15	120.0
C6—C7—H7B	109.1	C14—C15—H15	120.0
H7A—C7—H7B	107.8	C15—C16—C11	121.0 (2)
N1—C8—C7	109.4 (2)	C15—C16—H16	119.5
N1—C8—H8A	109.8	C11—C16—H16	119.5
C7—C8—H8A	109.8	C11—N1—C9	113.42 (19)
N1—C8—H8B	109.8	C11—N1—C8	116.3 (2)
C7—C8—H8B	109.8	C9—N1—C8	112.3 (2)
C6—C1—C2—C3	−0.1 (4)	N1—C11—C12—C13	179.1 (2)
C9—C1—C2—C3	178.9 (3)	C11—C12—C13—C14	−0.1 (4)
C1—C2—C3—C4	−0.4 (5)	C12—C13—C14—C15	0.1 (4)
C2—C3—C4—C5	0.3 (5)	C12—C13—C14—I1	−178.6 (2)
C3—C4—C5—C6	0.2 (5)	C13—C14—C15—C16	0.2 (4)
C2—C1—C6—C5	0.5 (4)	I1—C14—C15—C16	178.9 (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—C15	0.4 (4)
C9—C1—C6—C7	4.8 (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—C7	176.1 (3)	C12—C11—N1—C9	61.0 (3)
C1—C6—C7—C8	−22.5 (4)	C16—C11—N1—C8	12.6 (3)
C5—C6—C7—C8	160.9 (3)	C12—C11—N1—C8	−166.6 (2)
C6—C7—C8—N1	50.9 (3)	C10—C9—N1—C11	57.7 (3)
C6—C1—C9—N1	−16.1 (3)	C1—C9—N1—C11	−179.7 (2)
C2—C1—C9—N1	165.0 (2)	C10—C9—N1—C8	−76.6 (3)
C6—C1—C9—C10	107.4 (3)	C1—C9—N1—C8	46.0 (3)
C2—C1—C9—C10	−71.5 (3)	C7—C8—N1—C11	162.7 (2)
C16—C11—C12—C13	−0.1 (4)	C7—C8—N1—C9	−64.4 (3)

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Cgi	0.93	2.93	3.449 (4)	117

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯Cgi	0.93	2.93	3.449 (4)	117

Symmetry code: (i) .