4-[(2-Hydr-oxy-1-naphth-yl)(piperidin-1-yl)meth-yl]benzonitrile.

In the title compound, C(23)H(22)N(2)O, obtained from the condensation reaction of 4-formyl-benzonitrile, 2-naphthol and piperidine, the dihedral angle between the naphthalene ring system and the benzene ring is 75.31 (4)°. The piperidine ring adopts a chair conformation. The crystal structure is stabilized by inter-molecular C-H⋯N hydrogen bonds, which link the mol-ecules into centrosymmetric dimers. An intra-molecular O-H⋯N hydrogen bond is also present.

Related literature

For applications of Betti-type reactions, see: Zhao & Li et al. (2004 ▶); Lu et al. (2002 ▶); Xu et al. (2004 ▶); Wang et al. (2005 ▶)

Experimental

Crystal data

C23H22N2O

M = 342.43

Monoclinic,

a = 6.9989 (6) Å

b = 15.588 (1) Å

c = 17.211 (1) Å

β = 101.207 (2)°

V = 1841.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.2 × 0.1 × 0.1 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear, Rigaku, 2005 ▶) T min = 0.98, T max = 0.98

10945 measured reflections

3245 independent reflections

2661 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.108

S = 1.05

3245 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.13 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/PC (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033728/lx2110sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033728/lx2110Isup2.hkl

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

C23H22N2O	F(000) = 728
Mr = 342.43	Dx = 1.235 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3760 reflections
a = 6.9989 (6) Å	θ = 2.1–26.0°
b = 15.588 (1) Å	µ = 0.08 mm−1
c = 17.211 (1) Å	T = 296 K
β = 101.207 (2)°	Prism, colorless
V = 1841.9 (3) Å3	0.2 × 0.1 × 0.1 mm
Z = 4

Rigaku SCXmini diffractometer	3245 independent reflections
Radiation source: fine-focus sealed tube	2661 reflections with I > 2σ(I)
graphite	Rint = 0.023
CCD_Profile_fitting scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (CrystalClear, Rigaku, 2005)	h = −6→8
Tmin = 0.98, Tmax = 0.98	k = −19→18
10945 measured reflections	l = −21→21

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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F2) = 0.108	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0474P)2 + 0.2574P] where P = (Fo2 + 2Fc2)/3
3245 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.13 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	0.4754 (2)	0.29551 (10)	0.68027 (8)	0.0440 (4)
C2	0.3079 (2)	0.33944 (11)	0.68632 (9)	0.0530 (4)
C3	0.1365 (2)	0.32981 (13)	0.62827 (11)	0.0654 (5)
H3	0.0261	0.3612	0.6326	0.078*
C4	0.1307 (2)	0.27582 (13)	0.56662 (10)	0.0646 (5)
H4	0.0163	0.2705	0.5290	0.078*
C5	0.2951 (2)	0.22744 (11)	0.55839 (9)	0.0525 (4)
C6	0.2914 (3)	0.16868 (12)	0.49529 (10)	0.0660 (5)
H6	0.1773	0.1627	0.4577	0.079*
C7	0.4480 (3)	0.12125 (12)	0.48807 (10)	0.0699 (5)
H7	0.4413	0.0827	0.4464	0.084*
C8	0.6191 (3)	0.13057 (12)	0.54346 (10)	0.0653 (5)
H8	0.7275	0.0980	0.5386	0.078*
C9	0.6308 (2)	0.18670 (10)	0.60497 (9)	0.0539 (4)
H9	0.7479	0.1918	0.6410	0.065*
C10	0.4703 (2)	0.23747 (10)	0.61557 (8)	0.0444 (4)
C11	0.6626 (2)	0.30548 (9)	0.74220 (8)	0.0413 (3)
H11	0.7723	0.2984	0.7150	0.050*
C12	0.6784 (2)	0.23582 (9)	0.80461 (8)	0.0420 (3)
C13	0.8360 (2)	0.18047 (11)	0.81721 (9)	0.0552 (4)
H13	0.9315	0.1863	0.7868	0.066*
C14	0.8543 (3)	0.11701 (11)	0.87378 (10)	0.0616 (5)
H14	0.9603	0.0799	0.8809	0.074*
C15	0.7144 (2)	0.10873 (10)	0.92003 (9)	0.0508 (4)
C16	0.5568 (2)	0.16398 (10)	0.90883 (9)	0.0524 (4)
H16	0.4634	0.1593	0.9404	0.063*
C17	0.5384 (2)	0.22595 (10)	0.85088 (9)	0.0487 (4)
H17	0.4301	0.2618	0.8426	0.058*
C18	0.7349 (2)	0.04403 (12)	0.98061 (10)	0.0602 (4)
C19	0.8407 (2)	0.39901 (10)	0.84592 (9)	0.0522 (4)
H19A	0.9609	0.3843	0.8290	0.063*
H19B	0.8212	0.3579	0.8860	0.063*
C20	0.8583 (3)	0.48792 (11)	0.88137 (10)	0.0648 (5)
H20A	0.9686	0.4897	0.9253	0.078*
H20B	0.7419	0.5010	0.9018	0.078*
C21	0.8851 (3)	0.55474 (11)	0.82047 (10)	0.0667 (5)
H21A	0.8842	0.6117	0.8431	0.080*
H21B	1.0093	0.5463	0.8046	0.080*
C22	0.7218 (3)	0.54656 (11)	0.74953 (11)	0.0644 (5)
H22A	0.7440	0.5860	0.7086	0.077*
H22B	0.5997	0.5621	0.7645	0.077*
C23	0.70745 (10)	0.45642 (4)	0.71727 (4)	0.0536 (4)
H23A	0.5997	0.4530	0.6724	0.064*
H23B	0.8260	0.4425	0.6987	0.064*
O1	0.29677 (10)	0.39454 (4)	0.74661 (4)	0.0697 (4)
H1	0.4335	0.4016	0.7749	0.094 (7)*
N1	0.75228 (10)	−0.00682 (4)	1.02933 (4)	0.0807 (5)
N2	0.67754 (10)	0.39314 (4)	0.77784 (4)	0.0440 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0432 (8)	0.0496 (9)	0.0387 (8)	0.0036 (7)	0.0065 (6)	0.0061 (7)
C2	0.0494 (9)	0.0591 (10)	0.0518 (9)	0.0081 (7)	0.0131 (7)	0.0037 (8)
C3	0.0420 (9)	0.0822 (13)	0.0717 (12)	0.0114 (8)	0.0105 (8)	0.0137 (10)
C4	0.0477 (10)	0.0830 (13)	0.0578 (10)	−0.0052 (9)	−0.0029 (8)	0.0136 (10)
C5	0.0512 (9)	0.0594 (11)	0.0440 (8)	−0.0103 (8)	0.0023 (7)	0.0102 (8)
C6	0.0754 (12)	0.0720 (12)	0.0439 (9)	−0.0245 (10)	−0.0050 (8)	0.0024 (9)
C7	0.0973 (15)	0.0600 (12)	0.0518 (10)	−0.0129 (11)	0.0128 (10)	−0.0106 (9)
C8	0.0822 (13)	0.0589 (11)	0.0544 (10)	0.0052 (9)	0.0123 (9)	−0.0108 (9)
C9	0.0580 (10)	0.0560 (10)	0.0459 (9)	0.0041 (8)	0.0055 (7)	−0.0043 (8)
C10	0.0487 (8)	0.0459 (9)	0.0378 (8)	−0.0035 (7)	0.0062 (6)	0.0065 (7)
C11	0.0429 (8)	0.0429 (8)	0.0385 (7)	0.0048 (6)	0.0086 (6)	−0.0007 (6)
C12	0.0470 (8)	0.0397 (8)	0.0369 (7)	0.0018 (6)	0.0023 (6)	−0.0046 (6)
C13	0.0564 (10)	0.0612 (11)	0.0494 (9)	0.0161 (8)	0.0139 (7)	0.0094 (8)
C14	0.0642 (11)	0.0632 (11)	0.0571 (10)	0.0230 (9)	0.0108 (9)	0.0128 (9)
C15	0.0601 (10)	0.0470 (9)	0.0418 (8)	0.0005 (7)	0.0015 (7)	0.0024 (7)
C16	0.0587 (10)	0.0518 (10)	0.0476 (9)	−0.0017 (8)	0.0122 (7)	0.0020 (7)
C17	0.0518 (9)	0.0440 (9)	0.0504 (9)	0.0058 (7)	0.0099 (7)	0.0015 (7)
C18	0.0642 (11)	0.0609 (11)	0.0526 (10)	0.0036 (8)	0.0042 (8)	0.0089 (9)
C19	0.0622 (10)	0.0503 (9)	0.0417 (8)	−0.0038 (8)	0.0040 (7)	0.0016 (7)
C20	0.0842 (13)	0.0561 (11)	0.0537 (10)	−0.0122 (9)	0.0126 (9)	−0.0089 (8)
C21	0.0853 (13)	0.0460 (10)	0.0701 (11)	−0.0093 (9)	0.0186 (10)	−0.0056 (9)
C22	0.0784 (12)	0.0445 (10)	0.0725 (11)	0.0058 (8)	0.0204 (10)	0.0086 (9)
C23	0.0667 (10)	0.0486 (9)	0.0453 (9)	0.0064 (8)	0.0101 (7)	0.0076 (7)
O1	0.0583 (8)	0.0808 (9)	0.0726 (8)	0.0192 (6)	0.0193 (6)	−0.0094 (7)
N1	0.0778 (11)	0.0886 (12)	0.0752 (10)	0.0136 (9)	0.0138 (9)	0.0347 (10)
N2	0.0529 (7)	0.0407 (7)	0.0382 (6)	0.0048 (5)	0.0081 (6)	0.0009 (5)

C1—C2	1.379 (2)	C14—C15	1.383 (2)
C1—C10	1.430 (2)	C14—H14	0.9300
C1—C11	1.528 (2)	C15—C16	1.384 (2)
C2—O1	1.3609 (2)	C15—C18	1.438 (2)
C2—C3	1.412 (2)	C16—C17	1.377 (2)
C3—C4	1.348 (2)	C16—H16	0.9300
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.406 (2)	C18—N1	1.1430 (18)
C4—H4	0.9300	C19—N2	1.4713 (16)
C5—C6	1.417 (2)	C19—C20	1.510 (2)
C5—C10	1.424 (2)	C19—H19A	0.9700
C6—C7	1.348 (3)	C19—H19B	0.9700
C6—H6	0.9300	C20—C21	1.515 (2)
C7—C8	1.386 (3)	C20—H20A	0.9700
C7—H7	0.9300	C20—H20B	0.9700
C8—C9	1.363 (2)	C21—C22	1.507 (2)
C8—H8	0.9300	C21—H21A	0.9700
C9—C10	1.415 (2)	C21—H21B	0.9700
C9—H9	0.9300	C22—C23	1.5069 (18)
C11—N2	1.4931 (2)	C22—H22A	0.9700
C11—C12	1.5163 (19)	C22—H22B	0.9700
C11—H11	0.9800	C23—N2	1.4793
C12—C13	1.384 (2)	C23—H23A	0.9700
C12—C17	1.386 (2)	C23—H23B	0.9700
C13—C14	1.376 (2)	O1—H1	0.9916
C13—H13	0.9300
C2—C1—C10	118.69 (13)	C14—C15—C16	119.78 (14)
C2—C1—C11	121.54 (13)	C14—C15—C18	120.07 (15)
C10—C1—C11	119.74 (12)	C16—C15—C18	120.15 (15)
O1—C2—C1	123.11 (14)	C17—C16—C15	119.83 (15)
O1—C2—C3	116.13 (14)	C17—C16—H16	120.1
C1—C2—C3	120.75 (15)	C15—C16—H16	120.1
C4—C3—C2	121.00 (16)	C16—C17—C12	121.15 (14)
C4—C3—H3	119.5	C16—C17—H17	119.4
C2—C3—H3	119.5	C12—C17—H17	119.4
C3—C4—C5	120.90 (16)	N1—C18—C15	179.28 (18)
C3—C4—H4	119.6	N2—C19—C20	111.64 (13)
C5—C4—H4	119.6	N2—C19—H19A	109.3
C4—C5—C6	122.03 (16)	C20—C19—H19A	109.3
C4—C5—C10	118.90 (15)	N2—C19—H19B	109.3
C6—C5—C10	119.07 (16)	C20—C19—H19B	109.3
C7—C6—C5	122.08 (17)	H19A—C19—H19B	108.0
C7—C6—H6	119.0	C19—C20—C21	111.28 (14)
C5—C6—H6	119.0	C19—C20—H20A	109.4
C6—C7—C8	119.25 (17)	C21—C20—H20A	109.4
C6—C7—H7	120.4	C19—C20—H20B	109.4
C8—C7—H7	120.4	C21—C20—H20B	109.4
C9—C8—C7	121.01 (18)	H20A—C20—H20B	108.0
C9—C8—H8	119.5	C22—C21—C20	109.03 (15)
C7—C8—H8	119.5	C22—C21—H21A	109.9
C8—C9—C10	121.97 (16)	C20—C21—H21A	109.9
C8—C9—H9	119.0	C22—C21—H21B	109.9
C10—C9—H9	119.0	C20—C21—H21B	109.9
C9—C10—C5	116.63 (14)	H21A—C21—H21B	108.3
C9—C10—C1	123.65 (13)	C21—C22—C23	111.30 (13)
C5—C10—C1	119.71 (14)	C21—C22—H22A	109.4
N2—C11—C12	112.00 (10)	C23—C22—H22A	109.4
N2—C11—C1	111.23 (10)	C21—C22—H22B	109.4
C12—C11—C1	110.86 (11)	C23—C22—H22B	109.4
N2—C11—H11	107.5	H22A—C22—H22B	108.0
C12—C11—H11	107.5	N2—C23—C22	111.75 (7)
C1—C11—H11	107.5	N2—C23—H23A	109.3
C13—C12—C17	118.14 (14)	C22—C23—H23A	109.3
C13—C12—C11	120.24 (13)	N2—C23—H23B	109.3
C17—C12—C11	121.61 (13)	C22—C23—H23B	109.3
C14—C13—C12	121.40 (15)	H23A—C23—H23B	107.9
C14—C13—H13	119.3	C2—O1—H1	104.6
C12—C13—H13	119.3	C19—N2—C23	109.00 (7)
C13—C14—C15	119.67 (15)	C19—N2—C11	111.46 (9)
C13—C14—H14	120.2	C23—N2—C11	109.20 (6)
C15—C14—H14	120.2
C10—C1—C2—O1	178.47 (12)	N2—C11—C12—C13	−114.13 (14)
C11—C1—C2—O1	0.41 (2)	C1—C11—C12—C13	121.01 (15)
C10—C1—C2—C3	−2.3 (2)	N2—C11—C12—C17	65.30 (16)
C11—C1—C2—C3	179.62 (14)	C1—C11—C12—C17	−59.56 (17)
O1—C2—C3—C4	−178.99 (15)	C17—C12—C13—C14	0.2 (2)
C1—C2—C3—C4	1.8 (3)	C11—C12—C13—C14	179.64 (15)
C2—C3—C4—C5	0.0 (3)	C12—C13—C14—C15	−1.0 (3)
C3—C4—C5—C6	178.39 (16)	C13—C14—C15—C16	0.3 (3)
C3—C4—C5—C10	−1.2 (2)	C13—C14—C15—C18	−178.43 (16)
C4—C5—C6—C7	−178.88 (17)	C14—C15—C16—C17	1.1 (2)
C10—C5—C6—C7	0.7 (2)	C18—C15—C16—C17	179.81 (14)
C5—C6—C7—C8	−0.7 (3)	C15—C16—C17—C12	−1.8 (2)
C6—C7—C8—C9	0.1 (3)	C13—C12—C17—C16	1.2 (2)
C7—C8—C9—C10	0.4 (3)	C11—C12—C17—C16	−178.23 (13)
C8—C9—C10—C5	−0.3 (2)	C14—C15—C18—N1	90 (16)
C8—C9—C10—C1	178.46 (15)	C16—C15—C18—N1	−89 (16)
C4—C5—C10—C9	179.41 (14)	N2—C19—C20—C21	−57.87 (19)
C6—C5—C10—C9	−0.2 (2)	C19—C20—C21—C22	54.4 (2)
C4—C5—C10—C1	0.6 (2)	C20—C21—C22—C23	−54.38 (19)
C6—C5—C10—C1	−179.01 (14)	C21—C22—C23—N2	57.88 (14)
C2—C1—C10—C9	−177.59 (15)	C20—C19—N2—C23	58.52 (13)
C11—C1—C10—C9	0.5 (2)	C20—C19—N2—C11	179.12 (12)
C2—C1—C10—C5	1.2 (2)	C22—C23—N2—C19	−58.58 (11)
C11—C1—C10—C5	179.26 (13)	C22—C23—N2—C11	179.46 (11)
C2—C1—C11—N2	−30.85 (18)	C12—C11—N2—C19	46.39 (14)
C10—C1—C11—N2	151.10 (12)	C1—C11—N2—C19	171.07 (11)
C2—C1—C11—C12	94.46 (16)	C12—C11—N2—C23	166.88 (8)
C10—C1—C11—C12	−83.59 (16)	C1—C11—N2—C23	−68.46 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.99	1.70	2.614	151
C14—H14···N1i	0.93	2.55	3.395 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.99	1.70	2.614	151
C14—H14⋯N1i	0.93	2.55	3.395 (2)	151

Symmetry code: (i) .