2-[(E)-4-Quinolylmethyl-ideneamino]-phenol.

In the title compound, C(16)H(12)N(2)O, the dihedral angle between the two aromatic ring systems is 68.54 (5)°. The mol-ecular packing is stabilized by intra- and inter-molecular O-H⋯N and intra-molecular C-H⋯N hydrogen-bond inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For general background, see: Gao et al. (2005 ▶); Hagen et al. (1983 ▶); Lozytska et al. (2004 ▶); Sessler et al. (2004 ▶); Kuz’min et al. (2000 ▶). For related structures, see: Räisänen, Elo et al. (2007 ▶); Räisänen Leskelä & Repo (2007 ▶). For experimental procedures, see: Gümüş (2002 ▶).

Experimental

Crystal data

C16H12N2O

M = 248.28

Monoclinic,

a = 6.7174 (6) Å

b = 23.931 (2) Å

c = 7.7495 (6) Å

β = 105.521 (1)°

V = 1200.33 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 (2) K

0.25 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.978, T max = 0.991

12294 measured reflections

2991 independent reflections

2338 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.105

S = 1.05

2991 reflections

220 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033928/hb2807sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033928/hb2807Isup2.hkl

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

C16H12N2O	F(000) = 520
Mr = 248.28	Dx = 1.374 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2762 reflections
a = 6.7174 (6) Å	θ = 2.9–26.4°
b = 23.931 (2) Å	µ = 0.09 mm−1
c = 7.7495 (6) Å	T = 150 K
β = 105.521 (1)°	Block, yellow
V = 1200.33 (17) Å3	0.25 × 0.20 × 0.10 mm
Z = 4

Bruker APEXII CCD diffractometer	2991 independent reflections
Radiation source: sealed tube	2338 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 28.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→8
Tmin = 0.978, Tmax = 0.991	k = −31→31
12294 measured reflections	l = −10→10

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)] = 0.042	Hydrogen site location: difmap and geom
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0424P)2 + 0.3303P] where P = (Fo2 + 2Fc2)/3
2991 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	1.06305 (16)	0.13183 (4)	0.54890 (14)	0.0340 (3)
N1	0.76446 (16)	0.10349 (4)	0.72156 (14)	0.0243 (3)
N2	0.80975 (16)	−0.03956 (5)	1.22446 (15)	0.0258 (3)
C1	0.8930 (2)	0.16414 (5)	0.52971 (17)	0.0264 (4)
C2	0.8697 (3)	0.20982 (6)	0.41486 (19)	0.0340 (4)
C3	0.6997 (3)	0.24448 (6)	0.3910 (2)	0.0372 (5)
C4	0.5529 (3)	0.23493 (6)	0.4839 (2)	0.0370 (5)
C5	0.5745 (2)	0.18955 (6)	0.59862 (19)	0.0313 (4)
C6	0.7433 (2)	0.15362 (5)	0.62205 (17)	0.0242 (4)
C7	0.72483 (19)	0.10243 (5)	0.87303 (17)	0.0235 (3)
C8	0.74355 (18)	0.05168 (5)	0.98390 (16)	0.0215 (3)
C9	0.78135 (19)	0.05904 (6)	1.16557 (17)	0.0236 (3)
C10	0.81518 (19)	0.01260 (6)	1.28017 (17)	0.0260 (4)
C11	0.76319 (18)	−0.04841 (5)	1.04285 (17)	0.0233 (3)
C12	0.72937 (18)	−0.00427 (5)	0.91566 (16)	0.0212 (3)
C13	0.67854 (19)	−0.01837 (6)	0.73121 (17)	0.0240 (4)
C14	0.6654 (2)	−0.07303 (6)	0.67751 (18)	0.0278 (4)
C15	0.7014 (2)	−0.11657 (6)	0.8042 (2)	0.0308 (4)
C16	0.7487 (2)	−0.10454 (5)	0.98290 (19)	0.0282 (4)
H1	1.068 (3)	0.1013 (9)	0.628 (3)	0.072 (6)*
H2	0.976 (3)	0.2161 (7)	0.350 (2)	0.044 (5)*
H3	0.686 (3)	0.2753 (7)	0.307 (2)	0.046 (5)*
H4	0.433 (3)	0.2587 (7)	0.469 (2)	0.042 (5)*
H5	0.468 (2)	0.1808 (6)	0.657 (2)	0.033 (4)*
H7	0.689 (2)	0.1376 (6)	0.929 (2)	0.031 (4)*
H9	0.788 (2)	0.0966 (6)	1.214 (2)	0.031 (4)*
H10	0.844 (2)	0.0186 (6)	1.409 (2)	0.024 (4)*
H13	0.653 (2)	0.0114 (6)	0.642 (2)	0.025 (4)*
H14	0.632 (2)	−0.0822 (6)	0.550 (2)	0.032 (4)*
H15	0.693 (2)	−0.1566 (7)	0.765 (2)	0.035 (4)*
H16	0.772 (2)	−0.1340 (7)	1.074 (2)	0.033 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0385 (6)	0.0322 (5)	0.0359 (6)	0.0058 (4)	0.0181 (4)	0.0097 (4)
N1	0.0246 (5)	0.0223 (5)	0.0254 (6)	0.0006 (4)	0.0055 (4)	0.0023 (4)
N2	0.0220 (5)	0.0295 (6)	0.0259 (6)	0.0025 (4)	0.0062 (4)	0.0040 (5)
C1	0.0343 (7)	0.0221 (6)	0.0214 (6)	−0.0012 (5)	0.0049 (5)	−0.0020 (5)
C2	0.0475 (9)	0.0274 (7)	0.0272 (7)	−0.0040 (6)	0.0100 (6)	0.0022 (6)
C3	0.0549 (10)	0.0214 (7)	0.0308 (8)	−0.0020 (6)	0.0037 (7)	0.0037 (6)
C4	0.0436 (9)	0.0238 (7)	0.0383 (8)	0.0074 (6)	0.0018 (7)	0.0010 (6)
C5	0.0335 (7)	0.0257 (7)	0.0328 (7)	0.0021 (6)	0.0057 (6)	0.0002 (6)
C6	0.0303 (7)	0.0185 (6)	0.0217 (6)	−0.0016 (5)	0.0036 (5)	−0.0009 (5)
C7	0.0226 (6)	0.0221 (6)	0.0249 (6)	0.0003 (5)	0.0050 (5)	−0.0017 (5)
C8	0.0168 (6)	0.0238 (6)	0.0238 (6)	−0.0003 (5)	0.0052 (4)	0.0004 (5)
C9	0.0211 (6)	0.0251 (6)	0.0248 (6)	−0.0007 (5)	0.0064 (5)	−0.0023 (5)
C10	0.0227 (6)	0.0345 (7)	0.0210 (6)	0.0009 (5)	0.0060 (5)	0.0005 (5)
C11	0.0173 (6)	0.0259 (6)	0.0269 (6)	0.0004 (5)	0.0062 (5)	0.0017 (5)
C12	0.0166 (6)	0.0234 (6)	0.0241 (6)	0.0000 (4)	0.0064 (4)	−0.0004 (5)
C13	0.0212 (6)	0.0266 (7)	0.0247 (6)	0.0006 (5)	0.0070 (5)	0.0001 (5)
C14	0.0249 (6)	0.0297 (7)	0.0285 (7)	−0.0002 (5)	0.0068 (5)	−0.0056 (5)
C15	0.0282 (7)	0.0240 (7)	0.0388 (8)	0.0006 (5)	0.0064 (6)	−0.0036 (6)
C16	0.0257 (7)	0.0224 (6)	0.0358 (7)	0.0012 (5)	0.0071 (5)	0.0036 (6)

O1—C1	1.3542 (17)	C11—C12	1.4210 (17)
O1—H1	0.95 (2)	C12—C13	1.4186 (18)
N1—C6	1.4126 (16)	C13—C14	1.368 (2)
N1—C7	1.2715 (17)	C14—C15	1.408 (2)
N2—C11	1.3740 (17)	C15—C16	1.366 (2)
N2—C10	1.3181 (19)	C2—H2	0.989 (19)
C1—C2	1.3918 (19)	C3—H3	0.972 (16)
C1—C6	1.4042 (19)	C4—H4	0.967 (19)
C2—C3	1.383 (3)	C5—H5	0.966 (14)
C3—C4	1.387 (3)	C7—H7	1.005 (15)
C4—C5	1.386 (2)	C9—H9	0.971 (15)
C5—C6	1.3957 (19)	C10—H10	0.975 (15)
C7—C8	1.4735 (17)	C13—H13	0.975 (15)
C8—C9	1.3734 (18)	C14—H14	0.978 (15)
C8—C12	1.4334 (17)	C15—H15	1.002 (17)
C9—C10	1.403 (2)	C16—H16	0.980 (16)
C11—C16	1.4161 (17)
C1—O1—H1	113.2 (13)	C13—C14—C15	120.70 (13)
C6—N1—C7	120.37 (11)	C14—C15—C16	120.07 (13)
C10—N2—C11	117.40 (11)	C11—C16—C15	120.62 (12)
O1—C1—C2	117.77 (13)	C1—C2—H2	118.1 (10)
C2—C1—C6	119.56 (13)	C3—C2—H2	121.6 (10)
O1—C1—C6	122.67 (11)	C2—C3—H3	118.1 (12)
C1—C2—C3	120.27 (16)	C4—C3—H3	121.3 (12)
C2—C3—C4	120.54 (14)	C3—C4—H4	121.7 (10)
C3—C4—C5	119.68 (16)	C5—C4—H4	118.6 (10)
C4—C5—C6	120.53 (14)	C4—C5—H5	120.4 (9)
N1—C6—C1	116.70 (11)	C6—C5—H5	118.9 (9)
C1—C6—C5	119.40 (12)	N1—C7—H7	121.0 (8)
N1—C6—C5	123.63 (12)	C8—C7—H7	115.6 (8)
N1—C7—C8	123.26 (11)	C8—C9—H9	119.5 (9)
C7—C8—C12	124.61 (11)	C10—C9—H9	120.4 (9)
C9—C8—C12	118.28 (11)	N2—C10—H10	117.1 (9)
C7—C8—C9	117.10 (11)	C9—C10—H10	119.1 (9)
C8—C9—C10	120.11 (13)	C12—C13—H13	119.3 (9)
N2—C10—C9	123.87 (12)	C14—C13—H13	119.9 (9)
N2—C11—C16	117.33 (11)	C13—C14—H14	120.0 (9)
C12—C11—C16	119.56 (12)	C15—C14—H14	119.3 (9)
N2—C11—C12	123.11 (11)	C14—C15—H15	120.7 (9)
C8—C12—C13	124.63 (11)	C16—C15—H15	119.2 (9)
C11—C12—C13	118.22 (11)	C11—C16—H16	117.5 (9)
C8—C12—C11	117.13 (11)	C15—C16—H16	121.8 (9)
C12—C13—C14	120.82 (12)
C7—N1—C6—C1	141.39 (13)	C7—C8—C9—C10	−175.57 (12)
C7—N1—C6—C5	−44.64 (19)	C12—C8—C9—C10	3.15 (19)
C6—N1—C7—C8	−179.98 (13)	C7—C8—C12—C11	176.39 (12)
C11—N2—C10—C9	−1.61 (19)	C7—C8—C12—C13	−5.5 (2)
C10—N2—C11—C12	2.52 (19)	C9—C8—C12—C11	−2.23 (18)
C10—N2—C11—C16	−177.36 (12)	C9—C8—C12—C13	175.91 (13)
O1—C1—C2—C3	−179.58 (13)	C8—C9—C10—N2	−1.3 (2)
C6—C1—C2—C3	−0.4 (2)	N2—C11—C12—C8	−0.62 (19)
O1—C1—C6—N1	−7.27 (18)	N2—C11—C12—C13	−178.87 (12)
O1—C1—C6—C5	178.49 (12)	C16—C11—C12—C8	179.26 (12)
C2—C1—C6—N1	173.54 (12)	C16—C11—C12—C13	1.00 (18)
C2—C1—C6—C5	−0.70 (19)	N2—C11—C16—C15	179.50 (13)
C1—C2—C3—C4	1.4 (2)	C12—C11—C16—C15	−0.4 (2)
C2—C3—C4—C5	−1.4 (2)	C8—C12—C13—C14	−179.03 (13)
C3—C4—C5—C6	0.4 (2)	C11—C12—C13—C14	−0.92 (19)
C4—C5—C6—N1	−173.12 (13)	C12—C13—C14—C15	0.2 (2)
C4—C5—C6—C1	0.7 (2)	C13—C14—C15—C16	0.4 (2)
N1—C7—C8—C9	153.65 (13)	C14—C15—C16—C11	−0.3 (2)
N1—C7—C8—C12	−25.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.95 (2)	2.34 (2)	2.7766 (16)	107.5 (15)
O1—H1···N2i	0.95 (2)	1.91 (2)	2.8085 (16)	156.4 (19)
C13—H13···N1	0.975 (15)	2.356 (14)	2.9776 (17)	121.0 (11)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.95 (2)	2.34 (2)	2.7766 (16)	107.5 (15)
O1—H1⋯N2i	0.95 (2)	1.91 (2)	2.8085 (16)	156.4 (19)
C13—H13⋯N1	0.975 (15)	2.356 (14)	2.9776 (17)	121.0 (11)

Symmetry code: (i) .