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

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

doi:10.1107/S1600536811019830

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2072

doi:10.1107/S1600536811019830

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

Yanni Ma,^a Lili Du,^b Qi Zhang,^a Fangjun Cao ^a and Le Zhou ^a ^*

^aCollege of Science, Northwest Agriculture and Forest University, Yangling 712100, People's Republic of China, and ^bCollege of Life Science, Northwest Agriculture and Forest University, Yangling 712100, People's Republic of China
^*Correspondence e-mail: zhoulechem@yahoo.com.cn

(Received 8 April 2011; accepted 25 May 2011; online 23 July 2011)

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⋯π interactions.

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_r = 360.18
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.024
wR(F²) = 0.062
S = 1.00
2604 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.42 e Å⁻³

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) -x, -y, -z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019830/rn2087sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811019830/rn2087Isup3.cml

checkCIF report

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.

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

	Fig. 1. The molecular of the title compound showing 30% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme.
	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

C₁₆H₁₃IN₂	F(000) = 704
M_r = 360.18	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0295P)² + 0.8261P] where P = (F_o² + 2F_c²)/3
2604 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₆H₁₃IN₂	V = 1410.5 (13) Å³
M_r = 360.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.347 (4) Å	µ = 2.26 mm⁻¹
b = 14.832 (8) Å	T = 296 K
c = 13.149 (7) Å	0.32 × 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)
T_min = 0.532, T_max = 0.728	R_int = 0.018
10475 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.062	H-atom parameters constrained
S = 1.00	Δρ_max = 0.55 e Å⁻³
2604 reflections	Δρ_min = −0.42 e Å⁻³
172 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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃IN₂
M_r	360.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.347 (4), 14.832 (8), 13.149 (7)
β (°)	100.157 (6)
V (Å³)	1410.5 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.26
Crystal size (mm)	0.32 × 0.17 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.532, 0.728
No. of measured, independent and observed [I > 2σ(I)] reflections	10475, 2604, 2185
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.062, 1.00
No. of reflections	2604
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.42

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z+1.

Acknowledgements

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

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Volume 67| Part 8| August 2011| Page o2072

doi:10.1107/S1600536811019830

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