2-{4-[(Quinolin-8-yl­oxy)meth­yl]phen­yl}benzonitrile

Wei, B.

doi:10.1107/S1600536811012724

organic compounds

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Volume 67| Part 5| May 2011| Page o1209

doi:10.1107/S1600536811012724

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2-{4-[(Quinolin-8-yloxy)methyl]phenyl}benzonitrile

Bin Wei ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: seuwei@126.com

(Received 31 March 2011; accepted 6 April 2011; online 29 April 2011)

In the title compound, C₂₃H₁₆N₂O, the bond angle at the O atom that connects the benzene ring and the quinoline ring system is 116.0 (2)°. The quinoline ring system make a dihedral angle of 16.5 (2)° with the adjacent benzene ring. The dihedral angle between the biphenyl benzene rings is 70.8 (2)°.

Related literature

For background to tetrazoles, see: Hang et al. (2009 ). For our investigation of tetrazole compounds and their coordination modes, see: Xiong et al. (2002 ). For the preparation of tetrazoles using in situ synthesis of tetrazole through cycloaddition between organotin azide and organic cyano groups, see: Chen et al. (2010 ); Ye et al. (2006 ).

Experimental

Crystal data

C₂₃H₁₆N₂O
M_r = 336.38
Orthorhombic, P b c a
a = 14.526 (4) Å
b = 8.957 (3) Å
c = 27.126 (8) Å
V = 3529.3 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.842, T_max = 1.000
36455 measured reflections
4036 independent reflections
2865 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.222
S = 1.24
4036 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012724/jh2278sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012724/jh2278Isup2.hkl

checkCIF report

Comment top

Tetrazole compounds have been studied for more than one hundred years and applied in various areas (Hang et al., 2009). As a part of systematic investigation of new tetrazole compounds and discovery of new coordination mode (Xiong et al., 2002), we get the synthesis of the title compound C22 H16 N2 O,and preparation of tetrazoles in situ synthesis of tetrazole through cycloaddition between organotin azide and organic cyano group (Ye et al., 2006; Chen et al., 2010).

In the asymmetric unit of the title compound, the planes angle between the two benzene rings is 70.8°. O1 connect quinoline ring and sartan ring with a 115.9 bond-angle and the bond length O1—C10 is 1.4261 (35) Å, O1—C9 is 1.3691 (33) Å). The quinoline ring make a small dihedral angle of 16.5° with adjacent benzene ring (Fig 1). Fig 2 shows that the molecules assemble as straight chain in the crystal structure along the a axis.

Related literature top

For background to tetrazoles, see: Hang et al. (2009). For our investigation of tetrazole compounds and their coordination modes, see: Xiong et al. (2002). For the preparation of tetrazoles using in situ synthesis of tetrazole through cycloaddition between organotin azide and organic cyano groups, see: Chen et al. (2010); Ye et al. (2006).

Experimental top

8-hydroxyquinoline(1.45 g,10 mmol) was added in a solution of 4'-Bromoethyl-2-cyanobiphenyl(2.71 g,10 mmol) in methanol(20 ml).After the mixture was stirred for 10 h at 355 K,the precipitate was filtered off and the solution was evaporated in vacuum. The crude product was then crystallized form ethanol to yield colourless prisms of the title compound.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Crystal structure of the title compound with view along the a axis. Intermolecular interactions are shown as dashed lines.

2-{4-[(Quinolin-8-yloxy)methyl]phenyl}benzonitrile top

Crystal data top

C₂₃H₁₆N₂O	D_x = 1.266 Mg m⁻³
M_r = 336.38	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 6593 reflections
a = 14.526 (4) Å	θ = 2.3–27.5°
b = 8.957 (3) Å	µ = 0.08 mm⁻¹
c = 27.126 (8) Å	T = 293 K
V = 3529.3 (18) Å³	Prism, colorless
Z = 8	0.20 × 0.20 × 0.20 mm
F(000) = 1408

Data collection top

Rigaku Mercury CCD diffractometer	4036 independent reflections
Radiation source: fine-focus sealed tube	2865 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 1.5°
ω scans	h = −18→18
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
T_min = 0.842, T_max = 1.000	l = −35→35
36455 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.082	H-atom parameters constrained
wR(F²) = 0.222	w = 1/[σ²(F_o²) + (0.0817P)² + 0.8691P] where P = (F_o² + 2F_c²)/3
S = 1.24	(Δ/σ)_max < 0.001
4036 reflections	Δρ_max = 0.19 e Å⁻³
235 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0000

Crystal data top

C₂₃H₁₆N₂O	V = 3529.3 (18) Å³
M_r = 336.38	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.526 (4) Å	µ = 0.08 mm⁻¹
b = 8.957 (3) Å	T = 293 K
c = 27.126 (8) Å	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku Mercury CCD diffractometer	4036 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2865 reflections with I > 2σ(I)
T_min = 0.842, T_max = 1.000	R_int = 0.073
36455 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.222	H-atom parameters constrained
S = 1.24	Δρ_max = 0.19 e Å⁻³
4036 reflections	Δρ_min = −0.22 e Å⁻³
235 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.28089 (13)	0.1887 (2)	0.29588 (6)	0.0503 (5)
N1	0.43511 (16)	0.3299 (3)	0.26974 (8)	0.0494 (6)
C8	0.38445 (18)	0.2633 (3)	0.23340 (9)	0.0421 (6)
C11	0.17557 (18)	0.1423 (3)	0.36270 (10)	0.0430 (6)
C10	0.2001 (2)	0.1096 (3)	0.30999 (10)	0.0501 (7)
H10A	0.2103	0.0032	0.3060	0.060*
H10B	0.1494	0.1383	0.2887	0.060*
C9	0.30312 (19)	0.1836 (3)	0.24685 (9)	0.0435 (6)
C4	0.4091 (2)	0.2693 (3)	0.18282 (10)	0.0481 (7)
C16	0.2179 (2)	0.2507 (4)	0.39095 (10)	0.0534 (7)
H16A	0.2675	0.3036	0.3781	0.064*
C17	0.0766 (2)	0.2387 (3)	0.50852 (10)	0.0502 (7)
C14	0.11330 (18)	0.2051 (3)	0.45827 (10)	0.0462 (6)
C7	0.2541 (2)	0.1086 (3)	0.21157 (11)	0.0542 (7)
H7A	0.2025	0.0537	0.2207	0.065*
C5	0.3561 (2)	0.1925 (4)	0.14748 (11)	0.0608 (8)
H5A	0.3727	0.1960	0.1144	0.073*
C22	0.1263 (2)	0.2008 (3)	0.55117 (10)	0.0540 (7)
C15	0.1872 (2)	0.2815 (4)	0.43839 (10)	0.0566 (8)
H15A	0.2167	0.3544	0.4570	0.068*
C13	0.0722 (2)	0.0939 (3)	0.42995 (11)	0.0536 (7)
H13A	0.0231	0.0399	0.4428	0.064*
C12	0.1033 (2)	0.0629 (3)	0.38308 (10)	0.0534 (7)
H12A	0.0753	−0.0125	0.3649	0.064*
C6	0.2808 (2)	0.1134 (4)	0.16163 (11)	0.0627 (9)
H6A	0.2465	0.0620	0.1382	0.075*
C2	0.5370 (2)	0.4211 (4)	0.20652 (13)	0.0682 (9)
H2A	0.5888	0.4776	0.1988	0.082*
C3	0.4879 (2)	0.3538 (4)	0.17066 (11)	0.0592 (8)
H3A	0.5059	0.3630	0.1379	0.071*
C1	0.5086 (2)	0.4045 (4)	0.25572 (12)	0.0626 (8)
H1A	0.5442	0.4492	0.2801	0.075*
C23	0.2152 (3)	0.1308 (4)	0.54694 (12)	0.0694 (9)
C21	0.0894 (3)	0.2274 (4)	0.59785 (12)	0.0677 (9)
H21A	0.1226	0.2013	0.6259	0.081*
C18	−0.0090 (2)	0.3026 (4)	0.51433 (13)	0.0685 (9)
H18A	−0.0434	0.3274	0.4866	0.082*
C20	0.0046 (3)	0.2917 (4)	0.60239 (14)	0.0755 (11)
H20A	−0.0200	0.3093	0.6335	0.091*
N2	0.2850 (3)	0.0735 (5)	0.54410 (13)	0.0980 (12)
C19	−0.0448 (3)	0.3306 (4)	0.56077 (16)	0.0808 (11)
H19A	−0.1021	0.3756	0.5639	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0526 (11)	0.0582 (12)	0.0403 (10)	−0.0130 (9)	0.0084 (8)	−0.0045 (8)
N1	0.0530 (14)	0.0500 (13)	0.0452 (13)	−0.0064 (11)	0.0065 (11)	−0.0081 (10)
C8	0.0484 (15)	0.0366 (13)	0.0413 (14)	0.0055 (11)	0.0039 (12)	−0.0010 (10)
C11	0.0430 (14)	0.0442 (14)	0.0419 (13)	−0.0008 (12)	0.0014 (11)	0.0029 (11)
C10	0.0508 (16)	0.0548 (17)	0.0446 (15)	−0.0085 (13)	0.0050 (12)	−0.0010 (12)
C9	0.0477 (15)	0.0438 (14)	0.0390 (13)	0.0023 (12)	0.0022 (11)	−0.0024 (11)
C4	0.0576 (17)	0.0451 (15)	0.0417 (14)	0.0078 (13)	0.0067 (13)	−0.0003 (11)
C16	0.0488 (16)	0.0679 (18)	0.0434 (15)	−0.0165 (14)	0.0076 (12)	0.0006 (13)
C17	0.0560 (17)	0.0472 (15)	0.0475 (16)	−0.0096 (13)	0.0073 (13)	0.0010 (12)
C14	0.0454 (15)	0.0493 (15)	0.0439 (14)	0.0000 (12)	0.0026 (12)	0.0031 (12)
C7	0.0549 (16)	0.0600 (18)	0.0477 (15)	−0.0070 (14)	0.0022 (14)	−0.0087 (13)
C5	0.071 (2)	0.073 (2)	0.0380 (15)	0.0056 (17)	0.0026 (14)	−0.0006 (14)
C22	0.0641 (19)	0.0542 (16)	0.0438 (15)	−0.0110 (15)	0.0077 (14)	−0.0029 (13)
C15	0.0585 (18)	0.0662 (19)	0.0452 (16)	−0.0195 (15)	0.0037 (13)	−0.0071 (14)
C13	0.0552 (17)	0.0577 (17)	0.0479 (15)	−0.0166 (14)	0.0076 (13)	0.0020 (13)
C12	0.0611 (18)	0.0536 (16)	0.0455 (15)	−0.0181 (14)	0.0011 (14)	−0.0025 (13)
C6	0.066 (2)	0.077 (2)	0.0458 (16)	−0.0022 (17)	−0.0065 (15)	−0.0132 (15)
C2	0.070 (2)	0.0615 (19)	0.073 (2)	−0.0180 (17)	0.0265 (18)	−0.0058 (17)
C3	0.072 (2)	0.0546 (17)	0.0515 (17)	−0.0007 (16)	0.0188 (16)	0.0033 (14)
C1	0.0637 (19)	0.0588 (18)	0.065 (2)	−0.0146 (16)	0.0060 (16)	−0.0129 (15)
C23	0.075 (2)	0.089 (3)	0.0438 (17)	0.001 (2)	−0.0009 (17)	0.0068 (16)
C21	0.089 (3)	0.066 (2)	0.0479 (17)	−0.0169 (19)	0.0109 (17)	−0.0081 (15)
C18	0.065 (2)	0.074 (2)	0.066 (2)	0.0056 (18)	0.0153 (17)	0.0038 (17)
C20	0.103 (3)	0.060 (2)	0.063 (2)	−0.014 (2)	0.036 (2)	−0.0132 (17)
N2	0.088 (3)	0.135 (3)	0.071 (2)	0.025 (2)	−0.0001 (19)	0.015 (2)
C19	0.080 (3)	0.070 (2)	0.092 (3)	0.005 (2)	0.036 (2)	−0.002 (2)

Geometric parameters (Å, º) top

O1—C9	1.369 (3)	C5—C6	1.359 (5)
O1—C10	1.423 (3)	C5—H5A	0.9300
N1—C1	1.316 (4)	C22—C21	1.395 (4)
N1—C8	1.367 (3)	C22—C23	1.441 (5)
C8—C4	1.419 (4)	C15—H15A	0.9300
C8—C9	1.427 (4)	C13—C12	1.378 (4)
C11—C16	1.381 (4)	C13—H13A	0.9300
C11—C12	1.383 (4)	C12—H12A	0.9300
C11—C10	1.503 (4)	C6—H6A	0.9300
C10—H10A	0.9700	C2—C3	1.349 (5)
C10—H10B	0.9700	C2—C1	1.405 (4)
C9—C7	1.369 (4)	C2—H2A	0.9300
C4—C5	1.409 (4)	C3—H3A	0.9300
C4—C3	1.410 (4)	C1—H1A	0.9300
C16—C15	1.390 (4)	C23—N2	1.139 (5)
C16—H16A	0.9300	C21—C20	1.365 (5)
C17—C18	1.378 (4)	C21—H21A	0.9300
C17—C22	1.405 (4)	C18—C19	1.385 (5)
C17—C14	1.494 (4)	C18—H18A	0.9300
C14—C15	1.383 (4)	C20—C19	1.382 (6)
C14—C13	1.393 (4)	C20—H20A	0.9300
C7—C6	1.410 (4)	C19—H19A	0.9300
C7—H7A	0.9300

C9—O1—C10	116.0 (2)	C21—C22—C23	119.4 (3)
C1—N1—C8	116.8 (2)	C17—C22—C23	120.0 (3)
N1—C8—C4	123.0 (2)	C14—C15—C16	120.8 (3)
N1—C8—C9	118.6 (2)	C14—C15—H15A	119.6
C4—C8—C9	118.4 (2)	C16—C15—H15A	119.6
C16—C11—C12	118.5 (3)	C12—C13—C14	120.8 (3)
C16—C11—C10	124.0 (2)	C12—C13—H13A	119.6
C12—C11—C10	117.4 (2)	C14—C13—H13A	119.6
O1—C10—C11	110.8 (2)	C13—C12—C11	120.9 (3)
O1—C10—H10A	109.5	C13—C12—H12A	119.5
C11—C10—H10A	109.5	C11—C12—H12A	119.5
O1—C10—H10B	109.5	C5—C6—C7	120.6 (3)
C11—C10—H10B	109.5	C5—C6—H6A	119.7
H10A—C10—H10B	108.1	C7—C6—H6A	119.7
O1—C9—C7	124.9 (3)	C3—C2—C1	118.8 (3)
O1—C9—C8	115.3 (2)	C3—C2—H2A	120.6
C7—C9—C8	119.8 (2)	C1—C2—H2A	120.6
C5—C4—C3	123.1 (3)	C2—C3—C4	120.0 (3)
C5—C4—C8	120.1 (3)	C2—C3—H3A	120.0
C3—C4—C8	116.8 (3)	C4—C3—H3A	120.0
C11—C16—C15	120.7 (3)	N1—C1—C2	124.5 (3)
C11—C16—H16A	119.6	N1—C1—H1A	117.7
C15—C16—H16A	119.6	C2—C1—H1A	117.7
C18—C17—C22	118.0 (3)	N2—C23—C22	178.8 (4)
C18—C17—C14	120.7 (3)	C20—C21—C22	120.0 (3)
C22—C17—C14	121.3 (3)	C20—C21—H21A	120.0
C15—C14—C13	118.2 (3)	C22—C21—H21A	120.0
C15—C14—C17	122.2 (3)	C17—C18—C19	121.2 (4)
C13—C14—C17	119.6 (2)	C17—C18—H18A	119.4
C9—C7—C6	120.9 (3)	C19—C18—H18A	119.4
C9—C7—H7A	119.5	C21—C20—C19	120.0 (3)
C6—C7—H7A	119.5	C21—C20—H20A	120.0
C6—C5—C4	120.2 (3)	C19—C20—H20A	120.0
C6—C5—H5A	119.9	C20—C19—C18	120.2 (4)
C4—C5—H5A	119.9	C20—C19—H19A	119.9
C21—C22—C17	120.6 (3)	C18—C19—H19A	119.9

C1—N1—C8—C4	1.3 (4)	C18—C17—C22—C23	178.7 (3)
C1—N1—C8—C9	−178.8 (3)	C14—C17—C22—C23	1.2 (4)
C9—O1—C10—C11	−171.6 (2)	C13—C14—C15—C16	1.7 (5)
C16—C11—C10—O1	8.7 (4)	C17—C14—C15—C16	−178.0 (3)
C12—C11—C10—O1	−174.3 (2)	C11—C16—C15—C14	−0.4 (5)
C10—O1—C9—C7	−0.4 (4)	C15—C14—C13—C12	−1.2 (5)
C10—O1—C9—C8	−179.8 (2)	C17—C14—C13—C12	178.6 (3)
N1—C8—C9—O1	3.3 (3)	C14—C13—C12—C11	−0.7 (5)
C4—C8—C9—O1	−176.8 (2)	C16—C11—C12—C13	2.0 (4)
N1—C8—C9—C7	−176.2 (3)	C10—C11—C12—C13	−175.2 (3)
C4—C8—C9—C7	3.7 (4)	C4—C5—C6—C7	0.8 (5)
N1—C8—C4—C5	177.1 (3)	C9—C7—C6—C5	0.2 (5)
C9—C8—C4—C5	−2.7 (4)	C1—C2—C3—C4	0.4 (5)
N1—C8—C4—C3	−2.5 (4)	C5—C4—C3—C2	−178.1 (3)
C9—C8—C4—C3	177.6 (2)	C8—C4—C3—C2	1.5 (4)
C12—C11—C16—C15	−1.4 (5)	C8—N1—C1—C2	0.9 (5)
C10—C11—C16—C15	175.6 (3)	C3—C2—C1—N1	−1.8 (5)
C18—C17—C14—C15	111.6 (4)	C21—C22—C23—N2	54 (24)
C22—C17—C14—C15	−71.0 (4)	C17—C22—C23—N2	−125 (23)
C18—C17—C14—C13	−68.1 (4)	C17—C22—C21—C20	−0.5 (5)
C22—C17—C14—C13	109.3 (3)	C23—C22—C21—C20	−179.0 (3)
O1—C9—C7—C6	178.1 (3)	C22—C17—C18—C19	0.7 (5)
C8—C9—C7—C6	−2.5 (4)	C14—C17—C18—C19	178.3 (3)
C3—C4—C5—C6	−179.8 (3)	C22—C21—C20—C19	0.0 (5)
C8—C4—C5—C6	0.5 (4)	C21—C20—C19—C18	0.9 (6)
C18—C17—C22—C21	0.1 (4)	C17—C18—C19—C20	−1.3 (6)
C14—C17—C22—C21	−177.4 (3)

Experimental details

Crystal data
Chemical formula	C₂₃H₁₆N₂O
M_r	336.38
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	14.526 (4), 8.957 (3), 27.126 (8)
V (Å³)	3529.3 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.842, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	36455, 4036, 2865
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.222, 1.24
No. of reflections	4036
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.22

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The author is grateful to the starter fund of Southeast University for the purchase of the diffractometer.

References

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