1-[Phen-yl(pyridin-2-yl-amino)-meth-yl]-2-naphthol.

The title compound, C(22)H(18)N(2)O, was synthesized from naphthalen-2-ol, benzaldehyde and pyridin-2-amine. In the crystal, mol-ecules are linked into centrosymmetric R(2) (2)(16) dimers by pairs of O-H⋯N hydrogen bonds. The mol-ecular conformation is stabilized by an N-H⋯O hydrogen bond. The dihedral angle between the naphthylene ring system and the phenyl ring is 72.86 (12)°.

Related literature

For the application of compounds derived from naphthalen-2-ol in catalytic asymmetric synthesis, see: Szatmari & Fulop (2004 ▶). For related structures, see: Wang & Zhao (2009 ▶); Zhao & Sun (2005 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H18N2O

M = 326.38

Triclinic,

a = 7.5841 (10) Å

b = 10.1890 (15) Å

c = 11.9745 (15) Å

α = 111.00 (3)°

β = 98.64 (5)°

γ = 90.83 (3)°

V = 851.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.18 × 0.15 × 0.12 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.982, T max = 0.990

8701 measured reflections

3841 independent reflections

1655 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.097

wR(F 2) = 0.218

S = 1.10

3841 reflections

230 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042327/bx2316sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042327/bx2316Isup2.hkl

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

C22H18N2O	Z = 2
Mr = 326.38	F(000) = 344
Triclinic, P1	Dx = 1.273 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5841 (10) Å	Cell parameters from 1326 reflections
b = 10.1890 (15) Å	θ = 2.7–27.4°
c = 11.9745 (15) Å	µ = 0.08 mm−1
α = 111.00 (3)°	T = 295 K
β = 98.64 (5)°	Prism, colourless
γ = 90.83 (3)°	0.18 × 0.15 × 0.12 mm
V = 851.7 (2) Å3

Rigaku SCXmini diffractometer	3841 independent reflections
Radiation source: fine-focus sealed tube	1655 reflections with I > 2σ(I)
graphite	Rint = 0.078
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.7°
CCD_Profile_fitting scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
Tmin = 0.982, Tmax = 0.990	l = −15→15
8701 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)] = 0.097	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.218	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0643P)2] where P = (Fo2 + 2Fc2)/3
3841 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.22 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
O1	1.0666 (3)	0.3873 (3)	0.8523 (2)	0.0617 (8)
H1A	1.1414	0.4523	0.8658	0.093*
N1	0.7935 (4)	0.2729 (3)	0.9263 (3)	0.0566 (9)
H1B	0.8964	0.3093	0.9682	0.068*
N2	0.6664 (4)	0.4120 (3)	1.0857 (3)	0.0530 (8)
C1	0.7861 (5)	0.1892 (4)	0.7972 (3)	0.0485 (9)
C2	0.7985 (5)	0.2805 (4)	0.7231 (3)	0.0470 (9)
C3	0.9439 (5)	0.3761 (4)	0.7531 (3)	0.0520 (10)
C4	0.9660 (6)	0.4595 (4)	0.6832 (4)	0.0642 (11)
H4	1.0659	0.5228	0.7041	0.077*
C5	0.8400 (6)	0.4467 (5)	0.5847 (4)	0.0700 (12)
H5	0.8559	0.5009	0.5384	0.084*
C6	0.6862 (6)	0.3526 (4)	0.5520 (3)	0.0604 (11)
C7	0.6633 (5)	0.2706 (4)	0.6231 (3)	0.0545 (10)
C8	0.5032 (6)	0.1824 (4)	0.5882 (4)	0.0720 (13)
H8	0.4822	0.1276	0.6331	0.086*
C9	0.3793 (7)	0.1749 (5)	0.4913 (5)	0.0960 (17)
H9	0.2751	0.1165	0.4718	0.115*
C10	0.4070 (8)	0.2538 (6)	0.4213 (5)	0.0990 (19)
H10	0.3222	0.2467	0.3542	0.119*
C11	0.5562 (7)	0.3408 (5)	0.4499 (4)	0.0817 (14)
H11	0.5740	0.3932	0.4024	0.098*
C12	0.9204 (5)	0.0761 (4)	0.7796 (3)	0.0488 (9)
C13	0.9214 (6)	−0.0125 (4)	0.8453 (3)	0.0650 (11)
H13	0.8439	0.0007	0.9010	0.078*
C14	1.0357 (7)	−0.1196 (5)	0.8290 (4)	0.0769 (13)
H14	1.0342	−0.1783	0.8732	0.092*
C15	1.1510 (6)	−0.1395 (5)	0.7479 (4)	0.0793 (13)
H15	1.2311	−0.2094	0.7388	0.095*
C16	1.1481 (6)	−0.0558 (4)	0.6801 (4)	0.0739 (13)
H16	1.2231	−0.0718	0.6226	0.089*
C17	1.0346 (5)	0.0526 (4)	0.6962 (3)	0.0607 (11)
H17	1.0355	0.1096	0.6506	0.073*
C18	0.6481 (5)	0.2977 (4)	0.9857 (3)	0.0476 (9)
C19	0.4937 (5)	0.2068 (4)	0.9475 (4)	0.0648 (12)
H19	0.4829	0.1254	0.8784	0.078*
C20	0.3584 (6)	0.2405 (5)	1.0143 (4)	0.0775 (13)
H20	0.2535	0.1820	0.9890	0.093*
C21	0.3736 (6)	0.3571 (5)	1.1164 (4)	0.0780 (13)
H21	0.2824	0.3802	1.1625	0.094*
C22	0.5309 (6)	0.4390 (5)	1.1480 (4)	0.0689 (12)
H22	0.5443	0.5195	1.2181	0.083*
H66	0.668 (4)	0.142 (3)	0.776 (3)	0.041 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0546 (17)	0.0668 (18)	0.0604 (17)	−0.0142 (13)	−0.0016 (13)	0.0244 (15)
N1	0.0449 (19)	0.068 (2)	0.0469 (18)	−0.0050 (15)	0.0048 (14)	0.0102 (17)
N2	0.054 (2)	0.053 (2)	0.0499 (18)	0.0025 (15)	0.0178 (15)	0.0124 (17)
C1	0.043 (2)	0.050 (2)	0.046 (2)	−0.0056 (18)	0.0043 (17)	0.0101 (19)
C2	0.054 (2)	0.042 (2)	0.043 (2)	0.0036 (18)	0.0096 (17)	0.0126 (18)
C3	0.050 (2)	0.056 (2)	0.050 (2)	0.0035 (19)	0.0076 (19)	0.019 (2)
C4	0.068 (3)	0.061 (3)	0.070 (3)	0.006 (2)	0.021 (2)	0.028 (2)
C5	0.087 (3)	0.074 (3)	0.063 (3)	0.027 (3)	0.021 (2)	0.038 (3)
C6	0.066 (3)	0.054 (3)	0.052 (2)	0.018 (2)	0.007 (2)	0.010 (2)
C7	0.062 (3)	0.047 (2)	0.048 (2)	0.0171 (19)	0.0106 (19)	0.009 (2)
C8	0.062 (3)	0.061 (3)	0.077 (3)	0.000 (2)	−0.012 (2)	0.016 (2)
C9	0.085 (4)	0.076 (3)	0.102 (4)	−0.002 (3)	−0.030 (3)	0.020 (3)
C10	0.110 (5)	0.081 (4)	0.072 (3)	0.024 (3)	−0.030 (3)	0.005 (3)
C11	0.102 (4)	0.080 (3)	0.058 (3)	0.037 (3)	0.003 (3)	0.022 (3)
C12	0.050 (2)	0.050 (2)	0.041 (2)	−0.0084 (17)	0.0033 (17)	0.0112 (19)
C13	0.078 (3)	0.060 (3)	0.058 (3)	−0.003 (2)	0.012 (2)	0.023 (2)
C14	0.106 (4)	0.056 (3)	0.075 (3)	0.015 (3)	0.015 (3)	0.032 (3)
C15	0.085 (4)	0.064 (3)	0.089 (3)	0.017 (2)	0.022 (3)	0.024 (3)
C16	0.086 (3)	0.053 (3)	0.085 (3)	0.011 (2)	0.033 (3)	0.019 (3)
C17	0.070 (3)	0.054 (3)	0.060 (2)	0.006 (2)	0.019 (2)	0.020 (2)
C18	0.046 (2)	0.051 (2)	0.048 (2)	−0.0019 (17)	0.0073 (17)	0.020 (2)
C19	0.060 (3)	0.064 (3)	0.057 (2)	−0.010 (2)	0.013 (2)	0.006 (2)
C20	0.054 (3)	0.096 (4)	0.083 (3)	−0.010 (2)	0.017 (2)	0.032 (3)
C21	0.063 (3)	0.096 (4)	0.078 (3)	0.009 (3)	0.033 (2)	0.027 (3)
C22	0.072 (3)	0.066 (3)	0.064 (3)	0.009 (2)	0.024 (2)	0.013 (2)

O1—C3	1.363 (4)	C9—H9	0.9300
O1—H1A	0.8194	C10—C11	1.349 (7)
N1—C18	1.378 (4)	C10—H10	0.9300
N1—C1	1.466 (4)	C11—H11	0.9300
N1—H1B	0.8596	C12—C17	1.378 (5)
N2—C18	1.325 (4)	C12—C13	1.393 (5)
N2—C22	1.335 (5)	C13—C14	1.381 (6)
C1—C2	1.508 (5)	C13—H13	0.9300
C1—C12	1.528 (5)	C14—C15	1.366 (6)
C1—H66	0.97 (3)	C14—H14	0.9300
C2—C3	1.376 (5)	C15—C16	1.371 (6)
C2—C7	1.427 (5)	C15—H15	0.9300
C3—C4	1.415 (5)	C16—C17	1.386 (5)
C4—C5	1.367 (5)	C16—H16	0.9300
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.413 (6)	C18—C19	1.394 (5)
C5—H5	0.9300	C19—C20	1.368 (5)
C6—C7	1.416 (5)	C19—H19	0.9300
C6—C11	1.418 (5)	C20—C21	1.354 (6)
C7—C8	1.415 (5)	C20—H20	0.9300
C8—C9	1.357 (6)	C21—C22	1.368 (6)
C8—H8	0.9300	C21—H21	0.9300
C9—C10	1.388 (7)	C22—H22	0.9300
C3—O1—H1A	109.5	C9—C10—H10	119.8
C18—N1—C1	125.0 (3)	C10—C11—C6	120.3 (5)
C18—N1—H1B	117.5	C10—C11—H11	119.9
C1—N1—H1B	117.5	C6—C11—H11	119.9
C18—N2—C22	117.9 (3)	C17—C12—C13	118.2 (4)
N1—C1—C2	112.2 (3)	C17—C12—C1	122.6 (3)
N1—C1—C12	110.8 (3)	C13—C12—C1	119.0 (3)
C2—C1—C12	114.6 (3)	C14—C13—C12	121.1 (4)
N1—C1—H66	102.0 (18)	C14—C13—H13	119.5
C2—C1—H66	109.0 (18)	C12—C13—H13	119.5
C12—C1—H66	107.4 (19)	C15—C14—C13	120.0 (4)
C3—C2—C7	119.2 (3)	C15—C14—H14	120.0
C3—C2—C1	119.0 (3)	C13—C14—H14	120.0
C7—C2—C1	121.7 (3)	C14—C15—C16	119.6 (4)
O1—C3—C2	117.8 (3)	C14—C15—H15	120.2
O1—C3—C4	121.0 (3)	C16—C15—H15	120.2
C2—C3—C4	121.2 (4)	C15—C16—C17	120.8 (4)
C5—C4—C3	119.7 (4)	C15—C16—H16	119.6
C5—C4—H4	120.2	C17—C16—H16	119.6
C3—C4—H4	120.2	C12—C17—C16	120.2 (4)
C4—C5—C6	121.2 (4)	C12—C17—H17	119.9
C4—C5—H5	119.4	C16—C17—H17	119.9
C6—C5—H5	119.4	N2—C18—N1	115.6 (3)
C5—C6—C7	119.0 (4)	N2—C18—C19	121.3 (3)
C5—C6—C11	120.6 (4)	N1—C18—C19	123.1 (4)
C7—C6—C11	120.4 (4)	C20—C19—C18	118.2 (4)
C8—C7—C6	116.1 (4)	C20—C19—H19	120.9
C8—C7—C2	124.3 (4)	C18—C19—H19	120.9
C6—C7—C2	119.6 (4)	C21—C20—C19	121.5 (4)
C9—C8—C7	122.3 (5)	C21—C20—H20	119.2
C9—C8—H8	118.9	C19—C20—H20	119.2
C7—C8—H8	118.9	C20—C21—C22	116.2 (4)
C8—C9—C10	120.5 (5)	C20—C21—H21	121.9
C8—C9—H9	119.8	C22—C21—H21	121.9
C10—C9—H9	119.8	N2—C22—C21	124.8 (4)
C11—C10—C9	120.4 (5)	N2—C22—H22	117.6
C11—C10—H10	119.8	C21—C22—H22	117.6
C18—N1—C1—C2	102.8 (4)	C8—C9—C10—C11	−1.1 (8)
C18—N1—C1—C12	−127.8 (4)	C9—C10—C11—C6	−0.1 (8)
N1—C1—C2—C3	56.8 (4)	C5—C6—C11—C10	−178.0 (5)
C12—C1—C2—C3	−70.6 (4)	C7—C6—C11—C10	1.7 (6)
N1—C1—C2—C7	−122.9 (4)	N1—C1—C12—C17	−132.7 (4)
C12—C1—C2—C7	109.6 (4)	C2—C1—C12—C17	−4.6 (5)
C7—C2—C3—O1	177.1 (3)	N1—C1—C12—C13	51.0 (4)
C1—C2—C3—O1	−2.7 (5)	C2—C1—C12—C13	179.1 (3)
C7—C2—C3—C4	−3.2 (5)	C17—C12—C13—C14	1.1 (6)
C1—C2—C3—C4	177.1 (3)	C1—C12—C13—C14	177.5 (4)
O1—C3—C4—C5	−179.5 (3)	C12—C13—C14—C15	0.4 (7)
C2—C3—C4—C5	0.8 (6)	C13—C14—C15—C16	−2.3 (7)
C3—C4—C5—C6	0.8 (6)	C14—C15—C16—C17	2.6 (7)
C4—C5—C6—C7	0.1 (6)	C13—C12—C17—C16	−0.7 (6)
C4—C5—C6—C11	179.8 (4)	C1—C12—C17—C16	−177.0 (3)
C5—C6—C7—C8	177.7 (4)	C15—C16—C17—C12	−1.1 (6)
C11—C6—C7—C8	−2.0 (5)	C22—N2—C18—N1	−178.6 (3)
C5—C6—C7—C2	−2.4 (5)	C22—N2—C18—C19	−1.1 (5)
C11—C6—C7—C2	177.9 (4)	C1—N1—C18—N2	−156.4 (3)
C3—C2—C7—C8	−176.2 (4)	C1—N1—C18—C19	26.2 (6)
C1—C2—C7—C8	3.6 (6)	N2—C18—C19—C20	1.7 (6)
C3—C2—C7—C6	4.0 (5)	N1—C18—C19—C20	179.0 (4)
C1—C2—C7—C6	−176.3 (3)	C18—C19—C20—C21	−1.4 (7)
C6—C7—C8—C9	0.8 (6)	C19—C20—C21—C22	0.4 (7)
C2—C7—C8—C9	−179.1 (4)	C18—N2—C22—C21	0.1 (6)
C7—C8—C9—C10	0.7 (7)	C20—C21—C22—N2	0.3 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2i	0.82	1.87	2.677 (4)	170
N1—H1B···O1	0.86	2.35	2.767 (4)	110

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N2i	0.82	1.87	2.677 (4)	170
N1—H1B⋯O1	0.86	2.35	2.767 (4)	110

Symmetry code: (i) .