4-[(2-Hy-droxy-naphthalen-1-yl)(morpholin-4-yl)meth-yl]benzonitrile.

The title compound, C(22)H(20)N(2)O(2), was synthesized via a multicomponent reaction using naphthalen-2-ol, morpholine and 4-formyl-benzonitrile. The dihedral angle between the naphthalene ring system and the benzene ring is 81.25 (10)°. The morpholine ring adopts a chair conformation. The mol-ecular conformation is stabilized by intra-molecular O-H⋯N and C-H⋯O hydrogen bonds. In the crystal, inter-molecular C-H⋯N hydrogen bonds link mol-ecules into helical chains running parallel to the c axis.

Related literature

For background to multi-component reactions, see: Devi & Bhuyan (2004 ▶); Domling & Ugi (2000 ▶). Hulme & Gore (2003 ▶); Ugi (1962 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C22H20N2O2

M = 344.40

Trigonal,

a = 18.294 (3) Å

c = 28.738 (6) Å

V = 8329 (4) Å3

Z = 18

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.20 × 0.15 × 0.10 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.910, T max = 1.000

24077 measured reflections

3326 independent reflections

1786 reflections with I > 2σ(I)

R int = 0.138

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.210

S = 1.03

3326 reflections

235 parameters

7 restraints

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.27 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: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104997X/rz2668sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104997X/rz2668Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104997X/rz2668Isup3.cml

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

C22H20N2O2	Dx = 1.236 Mg m−3
Mr = 344.40	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 3326 reflections
Hall symbol: -R 3	θ = 3.1–25.2°
a = 18.294 (3) Å	µ = 0.08 mm−1
c = 28.738 (6) Å	T = 298 K
V = 8329 (4) Å3	Block, colourless
Z = 18	0.20 × 0.15 × 0.10 mm
F(000) = 3276

Rigaku Mercury2 diffractometer	3326 independent reflections
Radiation source: fine-focus sealed tube	1786 reflections with I > 2σ(I)
graphite	Rint = 0.138
Detector resolution: 13.6612 pixels mm-1	θmax = 25.2°, θmin = 3.1°
CCD profile fitting scans	h = −21→21
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −21→21
Tmin = 0.910, Tmax = 1.000	l = −34→34
24077 measured reflections

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0825P)2 + 7.1283P] where P = (Fo2 + 2Fc2)/3
3326 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.22 e Å−3
7 restraints	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.6590 (2)	0.9543 (2)	−0.01901 (11)	0.0550 (9)
N1	0.58212 (15)	0.86806 (15)	0.04966 (8)	0.0455 (7)
O1	0.51037 (19)	0.90933 (18)	−0.01526 (10)	0.0841 (9)
H1	0.5181	0.8920	0.0108	0.126*
C2	0.5846 (3)	0.9432 (2)	−0.03881 (13)	0.0713 (12)
N2	0.7870 (3)	1.3181 (3)	0.14213 (18)	0.146 (2)
O2	0.48604 (18)	0.71036 (17)	0.09733 (11)	0.0913 (10)
C3	0.5833 (5)	0.9667 (3)	−0.08470 (18)	0.110 (2)
H3A	0.5334	0.9598	−0.0972	0.132*
C4	0.6527 (7)	0.9991 (4)	−0.11117 (19)	0.140 (3)
H4A	0.6504	1.0157	−0.1414	0.168*
C5	0.7294 (5)	1.0085 (3)	−0.09428 (18)	0.119 (2)
C6	0.8038 (6)	1.0382 (4)	−0.1215 (2)	0.145 (3)
H6A	0.8020	1.0527	−0.1524	0.174*
C7	0.8752 (5)	1.0465 (4)	−0.1058 (3)	0.160 (4)
H7A	0.9223	1.0672	−0.1250	0.192*
C8	0.8794 (4)	1.0236 (3)	−0.0596 (2)	0.131 (2)
H8A	0.9289	1.0275	−0.0484	0.158*
C9	0.8103 (3)	0.9956 (2)	−0.03107 (17)	0.0894 (15)
H9A	0.8146	0.9826	−0.0003	0.107*
C10	0.7325 (3)	0.9858 (2)	−0.04718 (13)	0.0728 (12)
C11	0.66336 (19)	0.93938 (19)	0.03258 (10)	0.0459 (8)
H11A	0.7076	0.9249	0.0374	0.055*
C12	0.5716 (2)	0.7879 (2)	0.03122 (13)	0.0606 (10)
H12A	0.6184	0.7811	0.0413	0.073*
H12B	0.5719	0.7894	−0.0025	0.073*
C13	0.4897 (3)	0.7141 (2)	0.04806 (16)	0.0834 (13)
H13A	0.4428	0.7192	0.0363	0.100*
H13B	0.4842	0.6621	0.0360	0.100*
C14	0.4948 (3)	0.7858 (2)	0.11521 (14)	0.0771 (12)
H14A	0.4925	0.7828	0.1489	0.092*
H14B	0.4480	0.7922	0.1045	0.092*
C15	0.5765 (2)	0.8617 (2)	0.10044 (12)	0.0584 (9)
H15A	0.5798	0.9124	0.1132	0.070*
H15B	0.6235	0.8572	0.1126	0.070*
C16	0.6885 (2)	1.0214 (2)	0.05850 (10)	0.0478 (8)
C17	0.7626 (2)	1.0606 (2)	0.08376 (12)	0.0621 (10)
H17A	0.7954	1.0350	0.0863	0.075*
C18	0.7886 (2)	1.1370 (3)	0.10521 (13)	0.0733 (12)
H18A	0.8395	1.1633	0.1214	0.088*
C19	0.7396 (3)	1.1747 (2)	0.10287 (12)	0.0651 (11)
C20	0.6641 (2)	1.1355 (2)	0.07818 (12)	0.0626 (10)
H20A	0.6302	1.1600	0.0767	0.075*
C21	0.6400 (2)	1.0603 (2)	0.05593 (11)	0.0554 (9)
H21A	0.5902	1.0349	0.0388	0.067*
C22	0.7657 (3)	1.2544 (3)	0.12509 (16)	0.0976 (16)

	U11	U22	U33	U12	U13	U23
C1	0.086 (3)	0.047 (2)	0.036 (2)	0.036 (2)	0.0023 (19)	−0.0008 (15)
N1	0.0493 (16)	0.0456 (16)	0.0418 (16)	0.0238 (13)	0.0012 (12)	−0.0033 (12)
O1	0.090 (2)	0.090 (2)	0.084 (2)	0.0538 (18)	−0.0321 (17)	−0.0075 (16)
C2	0.118 (4)	0.054 (2)	0.045 (2)	0.045 (3)	−0.022 (2)	−0.0062 (18)
N2	0.126 (4)	0.096 (3)	0.153 (4)	0.008 (3)	0.030 (3)	−0.067 (3)
O2	0.106 (2)	0.0635 (19)	0.092 (2)	0.0338 (17)	0.0362 (18)	0.0195 (16)
C3	0.189 (6)	0.092 (4)	0.060 (3)	0.077 (4)	−0.045 (4)	−0.004 (3)
C4	0.280 (10)	0.078 (4)	0.047 (4)	0.078 (5)	−0.024 (5)	0.001 (3)
C5	0.231 (6)	0.043 (2)	0.049 (3)	0.043 (3)	0.054 (3)	0.005 (2)
C6	0.250 (6)	0.058 (3)	0.066 (3)	0.031 (4)	0.070 (4)	−0.002 (2)
C7	0.193 (7)	0.068 (4)	0.144 (7)	0.008 (5)	0.123 (6)	−0.008 (4)
C8	0.129 (5)	0.080 (3)	0.154 (6)	0.028 (3)	0.087 (4)	−0.007 (3)
C9	0.099 (4)	0.064 (3)	0.095 (3)	0.034 (3)	0.051 (3)	0.004 (2)
C10	0.112 (4)	0.041 (2)	0.055 (3)	0.031 (2)	0.028 (2)	−0.0009 (18)
C11	0.0470 (19)	0.049 (2)	0.044 (2)	0.0261 (17)	0.0012 (15)	0.0000 (15)
C12	0.068 (2)	0.052 (2)	0.063 (2)	0.0313 (19)	0.0085 (19)	0.0001 (17)
C13	0.086 (3)	0.048 (2)	0.098 (4)	0.021 (2)	0.013 (3)	−0.004 (2)
C14	0.083 (3)	0.068 (3)	0.077 (3)	0.036 (2)	0.026 (2)	0.010 (2)
C15	0.063 (2)	0.063 (2)	0.049 (2)	0.032 (2)	0.0085 (17)	0.0072 (17)
C16	0.048 (2)	0.053 (2)	0.0362 (19)	0.0210 (17)	0.0011 (15)	0.0025 (15)
C17	0.051 (2)	0.073 (3)	0.055 (2)	0.025 (2)	−0.0007 (17)	−0.0086 (19)
C18	0.051 (2)	0.083 (3)	0.059 (3)	0.014 (2)	0.0010 (18)	−0.020 (2)
C19	0.068 (3)	0.053 (2)	0.045 (2)	0.009 (2)	0.0174 (19)	−0.0085 (17)
C20	0.074 (3)	0.054 (2)	0.059 (2)	0.032 (2)	0.002 (2)	−0.0073 (18)
C21	0.065 (2)	0.049 (2)	0.052 (2)	0.0287 (19)	−0.0093 (17)	−0.0094 (17)
C22	0.081 (3)	0.073 (3)	0.088 (3)	0.000 (2)	0.024 (2)	−0.033 (3)

C1—C2	1.392 (5)	C9—H9A	0.9300
C1—C10	1.422 (5)	C11—C16	1.526 (4)
C1—C11	1.517 (4)	C11—H11A	0.9800
N1—C15	1.464 (4)	C12—C13	1.511 (5)
N1—C12	1.478 (4)	C12—H12A	0.9700
N1—C11	1.488 (4)	C12—H12B	0.9700
O1—C2	1.359 (5)	C13—H13A	0.9700
O1—H1	0.8517	C13—H13B	0.9700
C2—C3	1.391 (6)	C14—C15	1.505 (5)
N2—C22	1.137 (5)	C14—H14A	0.9700
O2—C14	1.405 (4)	C14—H14B	0.9700
O2—C13	1.418 (5)	C15—H15A	0.9700
C3—C4	1.337 (9)	C15—H15B	0.9700
C3—H3A	0.9300	C16—C17	1.381 (4)
C4—C5	1.410 (9)	C16—C21	1.389 (4)
C4—H4A	0.9300	C17—C18	1.377 (5)
C5—C6	1.423 (10)	C17—H17A	0.9300
C5—C10	1.425 (7)	C18—C19	1.379 (5)
C6—C7	1.317 (10)	C18—H18A	0.9300
C6—H6A	0.9300	C19—C20	1.391 (5)
C7—C8	1.403 (10)	C19—C22	1.437 (6)
C7—H7A	0.9300	C20—C21	1.374 (4)
C8—C9	1.373 (6)	C20—H20A	0.9300
C8—H8A	0.9300	C21—H21A	0.9300
C9—C10	1.420 (6)
C2—C1—C10	118.9 (4)	N1—C12—H12A	109.5
C2—C1—C11	120.6 (3)	C13—C12—H12A	109.5
C10—C1—C11	120.3 (3)	N1—C12—H12B	109.5
C15—N1—C12	108.1 (3)	C13—C12—H12B	109.5
C15—N1—C11	113.5 (2)	H12A—C12—H12B	108.1
C12—N1—C11	109.2 (2)	O2—C13—C12	111.4 (3)
C2—O1—H1	107.0	O2—C13—H13A	109.4
O1—C2—C3	116.4 (5)	C12—C13—H13A	109.4
O1—C2—C1	123.0 (3)	O2—C13—H13B	109.4
C3—C2—C1	120.6 (5)	C12—C13—H13B	109.4
C14—O2—C13	109.8 (3)	H13A—C13—H13B	108.0
C4—C3—C2	121.1 (6)	O2—C14—C15	112.1 (3)
C4—C3—H3A	119.4	O2—C14—H14A	109.2
C2—C3—H3A	119.4	C15—C14—H14A	109.2
C3—C4—C5	121.6 (5)	O2—C14—H14B	109.2
C3—C4—H4A	119.2	C15—C14—H14B	109.2
C5—C4—H4A	119.2	H14A—C14—H14B	107.9
C4—C5—C6	124.1 (7)	N1—C15—C14	110.6 (3)
C4—C5—C10	118.2 (6)	N1—C15—H15A	109.5
C6—C5—C10	117.6 (8)	C14—C15—H15A	109.5
C7—C6—C5	124.0 (8)	N1—C15—H15B	109.5
C7—C6—H6A	118.0	C14—C15—H15B	109.5
C5—C6—H6A	118.0	H15A—C15—H15B	108.1
C6—C7—C8	119.3 (6)	C17—C16—C21	118.4 (3)
C6—C7—H7A	120.3	C17—C16—C11	120.1 (3)
C8—C7—H7A	120.3	C21—C16—C11	121.5 (3)
C9—C8—C7	119.9 (7)	C18—C17—C16	120.9 (4)
C9—C8—H8A	120.0	C18—C17—H17A	119.6
C7—C8—H8A	120.0	C16—C17—H17A	119.6
C8—C9—C10	121.9 (5)	C17—C18—C19	120.3 (3)
C8—C9—H9A	119.0	C17—C18—H18A	119.8
C10—C9—H9A	119.0	C19—C18—H18A	119.8
C9—C10—C1	123.4 (4)	C18—C19—C20	119.5 (3)
C9—C10—C5	117.2 (5)	C18—C19—C22	121.1 (4)
C1—C10—C5	119.4 (5)	C20—C19—C22	119.4 (4)
N1—C11—C1	111.2 (3)	C21—C20—C19	119.5 (4)
N1—C11—C16	112.3 (2)	C21—C20—H20A	120.2
C1—C11—C16	108.5 (2)	C19—C20—H20A	120.2
N1—C11—H11A	108.3	C20—C21—C16	121.4 (3)
C1—C11—H11A	108.3	C20—C21—H21A	119.3
C16—C11—H11A	108.3	C16—C21—H21A	119.3
N1—C12—C13	110.6 (3)	N2—C22—C19	179.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.85	1.82	2.601 (4)	151.
C21—H21A···O1	0.93	2.54	3.300 (4)	139
C7—H7A···N2i	0.93	2.44	3.327 (9)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.85	1.82	2.601 (4)	151
C21—H21A⋯O1	0.93	2.54	3.300 (4)	139
C7—H7A⋯N2i	0.93	2.44	3.327 (9)	160

Symmetry code: (i) .