2-[4-(Morpholin-4-ylmeth-yl)phen-yl]benzonitrile.

In the title compound, C18H18N2O, the morpholine ring adopts a chair conformation with the exocyclic N-C bond in an equatorial orientation. The dihedral angles between the central benzene ring and the morpholine ring (all atoms) and the cyano-benzene ring are 87.87 (7) and 52.54 (7)°, respectively. No significant inter-molecular inter-actions are observed in the crystal structure.

Related literature

For biological applications of biphenyl derivatives see; Li et al. (2011 ▶); Hadizad et al. (2009 ▶); Larsen et al. (1994 ▶); Kamble et al. (2011 ▶); Zhang et al. (2004 ▶); Chan et al. (1994 ▶).

Experimental

Crystal data

C18H18N2O

M = 278.34

Monoclinic,

a = 21.1079 (5) Å

b = 8.1358 (1) Å

c = 9.0793 (2) Å

β = 100.833 (1)°

V = 1531.40 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.770, T max = 1.000

10319 measured reflections

2387 independent reflections

1948 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.083

S = 1.03

2387 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.10 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050957/hb7014sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050957/hb7014Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050957/hb7014Isup3.cml

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

C18H18N2O	F(000) = 592
Mr = 278.34	Dx = 1.207 Mg m−3
Monoclinic, P21/c	Melting point: 348 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 21.1079 (5) Å	Cell parameters from 2387 reflections
b = 8.1358 (1) Å	θ = 2.7–24.1°
c = 9.0793 (2) Å	µ = 0.08 mm−1
β = 100.833 (1)°	T = 296 K
V = 1531.40 (5) Å3	Plate, colourless
Z = 4	0.24 × 0.20 × 0.12 mm

Bruker SMART CCD diffractometer	2387 independent reflections
Radiation source: fine-focus sealed tube	1948 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω and φ scans	θmax = 24.1°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −18→24
Tmin = 0.770, Tmax = 1.000	k = −9→9
10319 measured reflections	l = −10→10

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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.0398P)2 + 0.1412P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2387 reflections	Δρmax = 0.11 e Å−3
191 parameters	Δρmin = −0.10 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0110 (13)

Experimental. Spectroscopic data IR (KBr): 3040–3080, 2175, 1500, 1H NMR (300 MHz, CDCl3, δ p.p.m..): 2.93 (t,4H, Morpholine CH2), 3.8 (s, 2H, CH2), 3.94 (t, 4H, morpholine CH2), 7.42- 7.84 (m, 8H, ArH). MS (m/z, 70 eV): 278, 250, 192.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.05263 (6)	0.66354 (15)	0.88307 (13)	0.0926 (4)
N2	0.11430 (4)	0.39688 (12)	0.76422 (10)	0.0462 (3)
N3	0.42812 (7)	0.18166 (17)	1.11979 (17)	0.0859 (4)
C4	0.10594 (8)	0.5807 (2)	0.96979 (18)	0.0835 (5)
H4A	0.0904	0.4927	1.0258	0.100*
H4B	0.1302	0.6568	1.0412	0.100*
C5	0.14930 (6)	0.51072 (17)	0.87289 (15)	0.0584 (4)
H5A	0.1667	0.5991	0.8209	0.070*
H5B	0.1851	0.4541	0.9351	0.070*
C6	0.05896 (6)	0.48231 (17)	0.67698 (15)	0.0585 (4)
H6A	0.0337	0.4060	0.6075	0.070*
H6B	0.0739	0.5695	0.6191	0.070*
C7	0.01763 (7)	0.5536 (2)	0.7778 (2)	0.0789 (5)
H7A	−0.0185	0.6112	0.7178	0.095*
H7B	0.0005	0.4654	0.8306	0.095*
C8	0.15600 (7)	0.33485 (18)	0.66566 (14)	0.0583 (4)
H8A	0.1782	0.4270	0.6304	0.070*
H8B	0.1293	0.2843	0.5788	0.070*
C9	0.20548 (6)	0.21152 (16)	0.73752 (13)	0.0504 (3)
C10	0.18769 (6)	0.07434 (16)	0.81104 (13)	0.0523 (3)
H10	0.1448	0.0608	0.8197	0.063*
C11	0.23247 (6)	−0.04191 (16)	0.87128 (13)	0.0507 (3)
H11	0.2193	−0.1331	0.9194	0.061*
C12	0.29698 (6)	−0.02548 (15)	0.86153 (14)	0.0491 (3)
C13	0.31476 (6)	0.11113 (16)	0.78798 (15)	0.0582 (4)
H13	0.3577	0.1251	0.7798	0.070*
C14	0.26966 (6)	0.22674 (17)	0.72675 (15)	0.0585 (4)
H14	0.2827	0.3170	0.6771	0.070*
C15	0.34412 (6)	−0.15362 (15)	0.92802 (15)	0.0527 (3)
C16	0.40058 (6)	−0.11543 (16)	1.02980 (16)	0.0566 (4)
C17	0.44281 (7)	−0.23758 (18)	1.09399 (18)	0.0706 (4)
H17	0.4801	−0.2099	1.1615	0.085*
C18	0.42949 (8)	−0.39895 (19)	1.0579 (2)	0.0776 (5)
H18	0.4578	−0.4810	1.1006	0.093*
C19	0.37458 (8)	−0.43904 (18)	0.9591 (2)	0.0789 (5)
H19	0.3655	−0.5487	0.9351	0.095*
C20	0.33248 (7)	−0.31866 (17)	0.89470 (18)	0.0687 (4)
H20	0.2954	−0.3486	0.8274	0.082*
C21	0.41517 (6)	0.05194 (18)	1.07696 (17)	0.0633 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0948 (8)	0.0848 (8)	0.0920 (8)	0.0435 (7)	0.0019 (7)	−0.0129 (6)
N2	0.0412 (6)	0.0469 (6)	0.0480 (6)	0.0037 (4)	0.0018 (4)	0.0029 (4)
N3	0.0726 (9)	0.0598 (9)	0.1148 (11)	−0.0027 (7)	−0.0098 (8)	−0.0077 (8)
C4	0.0912 (12)	0.0866 (11)	0.0668 (9)	0.0383 (9)	−0.0004 (9)	−0.0144 (9)
C5	0.0537 (8)	0.0582 (8)	0.0572 (8)	0.0045 (6)	−0.0051 (6)	−0.0016 (6)
C6	0.0477 (7)	0.0567 (8)	0.0651 (8)	0.0028 (6)	−0.0051 (6)	0.0076 (7)
C7	0.0517 (9)	0.0840 (12)	0.0987 (12)	0.0207 (8)	0.0079 (8)	0.0104 (10)
C8	0.0629 (8)	0.0654 (9)	0.0447 (7)	0.0125 (7)	0.0054 (6)	0.0041 (6)
C9	0.0529 (8)	0.0578 (8)	0.0394 (6)	0.0078 (6)	0.0062 (5)	−0.0035 (6)
C10	0.0434 (7)	0.0646 (8)	0.0488 (7)	0.0043 (6)	0.0081 (6)	−0.0036 (6)
C11	0.0491 (7)	0.0507 (7)	0.0525 (7)	−0.0014 (6)	0.0101 (6)	−0.0021 (6)
C12	0.0475 (7)	0.0463 (7)	0.0529 (7)	0.0029 (6)	0.0079 (6)	−0.0050 (6)
C13	0.0453 (7)	0.0593 (8)	0.0710 (8)	0.0027 (6)	0.0137 (6)	0.0035 (7)
C14	0.0578 (9)	0.0567 (8)	0.0618 (8)	0.0030 (7)	0.0132 (7)	0.0087 (7)
C15	0.0488 (7)	0.0467 (7)	0.0638 (8)	0.0037 (6)	0.0139 (6)	−0.0009 (6)
C16	0.0466 (8)	0.0482 (8)	0.0746 (9)	0.0051 (6)	0.0106 (7)	0.0021 (7)
C17	0.0530 (8)	0.0618 (9)	0.0932 (11)	0.0106 (7)	0.0044 (8)	0.0069 (8)
C18	0.0693 (10)	0.0554 (9)	0.1073 (12)	0.0191 (8)	0.0140 (9)	0.0113 (9)
C19	0.0840 (11)	0.0446 (8)	0.1079 (12)	0.0080 (8)	0.0171 (10)	−0.0030 (8)
C20	0.0637 (9)	0.0522 (9)	0.0874 (10)	0.0010 (7)	0.0070 (8)	−0.0079 (8)
C21	0.0458 (8)	0.0573 (9)	0.0821 (10)	0.0039 (7)	−0.0003 (7)	0.0027 (8)

O1—C7	1.4120 (19)	C10—C11	1.3758 (17)
O1—C4	1.4169 (18)	C10—H10	0.9300
N2—C5	1.4502 (16)	C11—C12	1.3873 (17)
N2—C8	1.4581 (16)	C11—H11	0.9300
N2—C6	1.4585 (15)	C12—C13	1.3843 (18)
N3—C21	1.1401 (18)	C12—C15	1.4886 (18)
C4—C5	1.496 (2)	C13—C14	1.3788 (18)
C4—H4A	0.9700	C13—H13	0.9300
C4—H4B	0.9700	C14—H14	0.9300
C5—H5A	0.9700	C15—C20	1.3881 (19)
C5—H5B	0.9700	C15—C16	1.3989 (18)
C6—C7	1.495 (2)	C16—C17	1.3880 (18)
C6—H6A	0.9700	C16—C21	1.443 (2)
C6—H6B	0.9700	C17—C18	1.369 (2)
C7—H7A	0.9700	C17—H17	0.9300
C7—H7B	0.9700	C18—C19	1.365 (2)
C8—C9	1.5057 (17)	C18—H18	0.9300
C8—H8A	0.9700	C19—C20	1.377 (2)
C8—H8B	0.9700	C19—H19	0.9300
C9—C14	1.3819 (18)	C20—H20	0.9300
C9—C10	1.3879 (18)
C7—O1—C4	109.55 (11)	C10—C9—C8	121.06 (12)
C5—N2—C8	110.46 (10)	C11—C10—C9	121.07 (12)
C5—N2—C6	108.59 (10)	C11—C10—H10	119.5
C8—N2—C6	110.24 (9)	C9—C10—H10	119.5
O1—C4—C5	111.35 (12)	C10—C11—C12	121.17 (12)
O1—C4—H4A	109.4	C10—C11—H11	119.4
C5—C4—H4A	109.4	C12—C11—H11	119.4
O1—C4—H4B	109.4	C13—C12—C11	117.81 (12)
C5—C4—H4B	109.4	C13—C12—C15	122.46 (11)
H4A—C4—H4B	108.0	C11—C12—C15	119.73 (11)
N2—C5—C4	110.69 (12)	C14—C13—C12	120.86 (12)
N2—C5—H5A	109.5	C14—C13—H13	119.6
C4—C5—H5A	109.5	C12—C13—H13	119.6
N2—C5—H5B	109.5	C13—C14—C9	121.47 (13)
C4—C5—H5B	109.5	C13—C14—H14	119.3
H5A—C5—H5B	108.1	C9—C14—H14	119.3
N2—C6—C7	110.63 (11)	C20—C15—C16	116.92 (12)
N2—C6—H6A	109.5	C20—C15—C12	120.77 (12)
C7—C6—H6A	109.5	C16—C15—C12	122.27 (11)
N2—C6—H6B	109.5	C17—C16—C15	121.23 (13)
C7—C6—H6B	109.5	C17—C16—C21	117.81 (13)
H6A—C6—H6B	108.1	C15—C16—C21	120.89 (11)
O1—C7—C6	111.65 (12)	C18—C17—C16	119.94 (15)
O1—C7—H7A	109.3	C18—C17—H17	120.0
C6—C7—H7A	109.3	C16—C17—H17	120.0
O1—C7—H7B	109.3	C19—C18—C17	119.81 (14)
C6—C7—H7B	109.3	C19—C18—H18	120.1
H7A—C7—H7B	108.0	C17—C18—H18	120.1
N2—C8—C9	114.47 (10)	C18—C19—C20	120.64 (14)
N2—C8—H8A	108.6	C18—C19—H19	119.7
C9—C8—H8A	108.6	C20—C19—H19	119.7
N2—C8—H8B	108.6	C19—C20—C15	121.46 (14)
C9—C8—H8B	108.6	C19—C20—H20	119.3
H8A—C8—H8B	107.6	C15—C20—H20	119.3
C14—C9—C10	117.62 (12)	N3—C21—C16	177.11 (16)
C14—C9—C8	121.26 (12)
C7—O1—C4—C5	58.34 (19)	C10—C9—C14—C13	−0.67 (19)
C8—N2—C5—C4	177.40 (11)	C8—C9—C14—C13	−177.75 (12)
C6—N2—C5—C4	56.40 (14)	C13—C12—C15—C20	−128.35 (15)
O1—C4—C5—N2	−58.71 (18)	C11—C12—C15—C20	51.08 (18)
C5—N2—C6—C7	−56.05 (15)	C13—C12—C15—C16	53.85 (18)
C8—N2—C6—C7	−177.18 (12)	C11—C12—C15—C16	−126.71 (14)
C4—O1—C7—C6	−58.19 (17)	C20—C15—C16—C17	0.0 (2)
N2—C6—C7—O1	58.11 (16)	C12—C15—C16—C17	177.92 (13)
C5—N2—C8—C9	73.85 (14)	C20—C15—C16—C21	−176.91 (13)
C6—N2—C8—C9	−166.14 (11)	C12—C15—C16—C21	1.0 (2)
N2—C8—C9—C14	−130.98 (13)	C15—C16—C17—C18	0.0 (2)
N2—C8—C9—C10	52.04 (16)	C21—C16—C17—C18	177.05 (15)
C14—C9—C10—C11	0.17 (18)	C16—C17—C18—C19	−0.2 (3)
C8—C9—C10—C11	177.25 (11)	C17—C18—C19—C20	0.3 (3)
C9—C10—C11—C12	0.45 (18)	C18—C19—C20—C15	−0.2 (2)
C10—C11—C12—C13	−0.56 (18)	C16—C15—C20—C19	0.1 (2)
C10—C11—C12—C15	179.98 (11)	C12—C15—C20—C19	−177.84 (13)
C11—C12—C13—C14	0.05 (19)	C17—C16—C21—N3	−25 (3)
C15—C12—C13—C14	179.50 (12)	C15—C16—C21—N3	152 (3)
C12—C13—C14—C9	0.6 (2)