2-(7-Hydr-oxy-2-naphth-yloxy)-N-(6-methyl-2-pyrid-yl)acetamide.

In the title compound, C(18)H(16)N(2)O(3), the dihedral angle between the naphthalene ring system and the pyridyl ring is 18.1 (8)°. The mol-ecules are inter-connected via C-H⋯O and O-H⋯O hydrogen bonds. Inversion-related mol-ecules are linked by O-H⋯O hydrogen bonds into cyclic centrosymmetric R(2) (2)(22) dimers. Intra-molecular N-H⋯O hydrogen bonding produces an S(5) ring motif. The crystal structure is further stabilized by weak C-H-π inter-actions.

Related literature

For related literature on the applications; see: Atwood et al. (1996 ▶); Garcia-Tellado et al. (1990 ▶); Ghosh & Masanta (2006 ▶). For comparison bond lengths and angles see: Jin & Jin (2005 ▶); Liu & Li (2004 ▶); Rozycka-Sokolowska et al. (2004 ▶).

Experimental

Crystal data

C18H16N2O3

M = 308.33

Triclinic,

a = 5.3676 (3) Å

b = 11.6991 (7) Å

c = 12.2915 (6) Å

α = 104.994 (4)°

β = 94.777 (3)°

γ = 94.877 (4)°

V = 738.42 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100.0 (1) K

0.4 × 0.16 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.963, T max = 0.992

12299 measured reflections

3340 independent reflections

2480 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.130

S = 1.08

3340 reflections

217 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808006211/ng2430sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006211/ng2430Isup2.hkl

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

C18H16N2O3	Z = 2
Mr = 308.33	F000 = 324
Triclinic, P1	Dx = 1.387 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.3676 (3) Å	Cell parameters from 2511 reflections
b = 11.6991 (7) Å	θ = 3.4–30.4º
c = 12.2915 (6) Å	µ = 0.10 mm−1
α = 104.994 (4)º	T = 100.0 (1) K
β = 94.777 (3)º	Block, colourless
γ = 94.877 (4)º	0.4 × 0.16 × 0.09 mm
V = 738.42 (7) Å3

Bruker SMART APEXII CCD area-detector diffractometer	2480 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm-1	Rint = 0.046
T = 100.0(1) K	θmax = 27.5º
ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −6→6
Tmin = 0.963, Tmax = 0.992	k = −15→13
12299 measured reflections	l = −15→15
3340 independent reflections

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.2187P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.045	(Δ/σ)max < 0.001
wR(F2) = 0.130	Δρmax = 0.24 e Å−3
S = 1.08	Δρmin = −0.31 e Å−3
3340 reflections	Extinction correction: none
217 parameters

Geometry. Experimental. The low-temperature data was collected with the Oxford Crysosystem Cobra low-temperature attachement.All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
O1	−0.0438 (2)	0.40705 (11)	0.65093 (10)	0.0240 (3)
O2	−0.5889 (2)	0.23059 (11)	0.67844 (10)	0.0252 (3)
O3	0.8081 (2)	0.77389 (11)	1.13643 (11)	0.0245 (3)
N1	−0.3537 (3)	0.23114 (14)	0.53179 (13)	0.0225 (3)
N2	−0.3711 (3)	0.13147 (13)	0.34601 (12)	0.0204 (3)
C1	0.2212 (3)	0.52560 (15)	0.81993 (14)	0.0202 (4)
H1A	0.1222	0.4975	0.8681	0.024*
C2	0.4376 (3)	0.60921 (15)	0.86540 (14)	0.0188 (4)
C3	0.5095 (3)	0.65141 (15)	0.98390 (14)	0.0201 (4)
H3A	0.4128	0.6258	1.0342	0.024*
C4	0.7222 (3)	0.73013 (15)	1.02417 (14)	0.0199 (4)
C5	0.8699 (3)	0.77091 (16)	0.94921 (15)	0.0222 (4)
H5A	1.0129	0.8245	0.9777	0.027*
C6	0.8034 (3)	0.73183 (15)	0.83490 (15)	0.0220 (4)
H6A	0.9019	0.759	0.786	0.026*
C7	0.5856 (3)	0.65024 (15)	0.79020 (14)	0.0194 (4)
C8	0.5140 (3)	0.60795 (16)	0.67167 (15)	0.0218 (4)
H8A	0.6104	0.6349	0.622	0.026*
C9	0.3063 (3)	0.52862 (16)	0.62984 (15)	0.0219 (4)
H9A	0.2608	0.5019	0.5521	0.026*
C10	0.1598 (3)	0.48687 (15)	0.70512 (15)	0.0212 (4)
C11	−0.2068 (3)	0.35993 (16)	0.71767 (15)	0.0214 (4)
H11A	−0.2874	0.4234	0.7641	0.026*
H11B	−0.111	0.3235	0.7675	0.026*
C12	−0.4042 (3)	0.26785 (15)	0.64022 (14)	0.0201 (4)
C13	−0.4891 (3)	0.14402 (15)	0.43903 (15)	0.0206 (4)
C14	−0.7171 (3)	0.08120 (16)	0.44454 (16)	0.0241 (4)
H14A	−0.7945	0.0941	0.511	0.029*
C15	−0.8235 (3)	−0.00193 (17)	0.34564 (16)	0.0259 (4)
H15A	−0.9753	−0.0469	0.3448	0.031*
C16	−0.7042 (3)	−0.01777 (16)	0.24877 (15)	0.0227 (4)
H16A	−0.7733	−0.0742	0.1826	0.027*
C17	−0.4792 (3)	0.05155 (15)	0.25079 (14)	0.0198 (4)
C18	−0.3482 (3)	0.04513 (16)	0.14692 (15)	0.0244 (4)
H18D	−0.1719	0.0416	0.1646	0.037*
H18A	−0.3712	0.1145	0.1209	0.037*
H18B	−0.4174	−0.0248	0.0887	0.037*
H1N1	−0.210 (4)	0.2626 (18)	0.5165 (17)	0.026 (5)*
H1O3	0.700 (5)	0.756 (2)	1.181 (2)	0.043 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0247 (6)	0.0271 (7)	0.0162 (6)	−0.0067 (5)	0.0001 (5)	0.0022 (5)
O2	0.0267 (6)	0.0274 (7)	0.0193 (7)	−0.0016 (5)	0.0039 (5)	0.0034 (5)
O3	0.0262 (6)	0.0291 (7)	0.0146 (7)	−0.0054 (5)	−0.0010 (5)	0.0031 (5)
N1	0.0234 (7)	0.0243 (8)	0.0165 (8)	−0.0042 (6)	0.0005 (6)	0.0021 (6)
N2	0.0226 (7)	0.0195 (7)	0.0174 (8)	−0.0006 (5)	−0.0010 (6)	0.0037 (6)
C1	0.0224 (8)	0.0214 (9)	0.0162 (9)	0.0007 (6)	0.0028 (7)	0.0042 (7)
C2	0.0210 (8)	0.0170 (8)	0.0174 (9)	0.0027 (6)	0.0020 (7)	0.0025 (7)
C3	0.0233 (8)	0.0205 (9)	0.0161 (9)	0.0001 (6)	0.0028 (7)	0.0048 (7)
C4	0.0233 (8)	0.0186 (9)	0.0159 (9)	0.0019 (6)	−0.0002 (7)	0.0020 (7)
C5	0.0219 (8)	0.0213 (9)	0.0211 (10)	−0.0015 (6)	0.0010 (7)	0.0035 (7)
C6	0.0238 (8)	0.0210 (9)	0.0207 (9)	−0.0011 (7)	0.0047 (7)	0.0051 (7)
C7	0.0231 (8)	0.0177 (8)	0.0168 (9)	0.0021 (6)	0.0022 (7)	0.0035 (7)
C8	0.0258 (8)	0.0216 (9)	0.0187 (9)	0.0034 (7)	0.0050 (7)	0.0058 (7)
C9	0.0281 (9)	0.0226 (9)	0.0133 (9)	0.0028 (7)	0.0008 (7)	0.0021 (7)
C10	0.0219 (8)	0.0182 (9)	0.0203 (9)	0.0021 (6)	−0.0012 (7)	0.0004 (7)
C11	0.0239 (8)	0.0219 (9)	0.0167 (9)	0.0009 (7)	0.0003 (7)	0.0031 (7)
C12	0.0241 (8)	0.0196 (9)	0.0158 (9)	0.0027 (7)	−0.0001 (7)	0.0038 (7)
C13	0.0241 (8)	0.0195 (9)	0.0165 (9)	0.0008 (6)	−0.0013 (7)	0.0033 (7)
C14	0.0251 (9)	0.0277 (10)	0.0186 (9)	−0.0014 (7)	0.0022 (7)	0.0062 (8)
C15	0.0240 (8)	0.0277 (10)	0.0241 (10)	−0.0060 (7)	−0.0029 (7)	0.0082 (8)
C16	0.0257 (8)	0.0205 (9)	0.0183 (9)	−0.0032 (7)	−0.0038 (7)	0.0028 (7)
C17	0.0233 (8)	0.0183 (8)	0.0168 (9)	0.0022 (6)	−0.0012 (7)	0.0039 (7)
C18	0.0272 (9)	0.0243 (9)	0.0183 (9)	0.0000 (7)	−0.0001 (7)	0.0016 (7)

O1—C10	1.376 (2)	C6—H6A	0.93
O1—C11	1.419 (2)	C7—C8	1.420 (2)
O2—C12	1.226 (2)	C8—C9	1.360 (2)
O3—C4	1.366 (2)	C8—H8A	0.93
O3—H1O3	0.88 (3)	C9—C10	1.415 (3)
N1—C12	1.348 (2)	C9—H9A	0.93
N1—C13	1.415 (2)	C11—C12	1.516 (2)
N1—H1N1	0.88 (2)	C11—H11A	0.97
N2—C13	1.334 (2)	C11—H11B	0.97
N2—C17	1.345 (2)	C13—C14	1.389 (2)
C1—C10	1.368 (2)	C14—C15	1.388 (2)
C1—C2	1.426 (2)	C14—H14A	0.93
C1—H1A	0.93	C15—C16	1.377 (3)
C2—C7	1.415 (2)	C15—H15A	0.93
C2—C3	1.420 (2)	C16—C17	1.391 (2)
C3—C4	1.374 (2)	C16—H16A	0.93
C3—H3A	0.93	C17—C18	1.496 (3)
C4—C5	1.411 (2)	C18—H18D	0.96
C5—C6	1.366 (2)	C18—H18A	0.96
C5—H5A	0.93	C18—H18B	0.96
C6—C7	1.418 (2)
C10—O1—C11	118.54 (13)	C1—C10—O1	125.35 (16)
C4—O3—H1O3	112.9 (16)	C1—C10—C9	121.31 (16)
C12—N1—C13	129.91 (15)	O1—C10—C9	113.33 (15)
C12—N1—H1N1	115.8 (13)	O1—C11—C12	109.16 (14)
C13—N1—H1N1	114.2 (13)	O1—C11—H11A	109.8
C13—N2—C17	117.79 (14)	C12—C11—H11A	109.8
C10—C1—C2	119.74 (17)	O1—C11—H11B	109.8
C10—C1—H1A	120.1	C12—C11—H11B	109.8
C2—C1—H1A	120.1	H11A—C11—H11B	108.3
C7—C2—C3	119.23 (15)	O2—C12—N1	125.19 (16)
C7—C2—C1	119.02 (15)	O2—C12—C11	120.00 (15)
C3—C2—C1	121.74 (16)	N1—C12—C11	114.78 (15)
C4—C3—C2	119.93 (16)	N2—C13—C14	124.72 (16)
C4—C3—H3A	120	N2—C13—N1	111.27 (15)
C2—C3—H3A	120	C14—C13—N1	124.00 (17)
O3—C4—C3	124.03 (16)	C15—C14—C13	116.46 (17)
O3—C4—C5	115.14 (15)	C15—C14—H14A	121.8
C3—C4—C5	120.83 (16)	C13—C14—H14A	121.8
C6—C5—C4	120.17 (15)	C16—C15—C14	120.03 (16)
C6—C5—H5A	119.9	C16—C15—H15A	120
C4—C5—H5A	119.9	C14—C15—H15A	120
C5—C6—C7	120.59 (17)	C15—C16—C17	119.32 (16)
C5—C6—H6A	119.7	C15—C16—H16A	120.3
C7—C6—H6A	119.7	C17—C16—H16A	120.3
C2—C7—C6	119.24 (15)	N2—C17—C16	121.65 (16)
C2—C7—C8	119.26 (15)	N2—C17—C18	116.05 (15)
C6—C7—C8	121.50 (16)	C16—C17—C18	122.26 (15)
C9—C8—C7	120.91 (17)	C17—C18—H18D	109.5
C9—C8—H8A	119.5	C17—C18—H18A	109.5
C7—C8—H8A	119.5	H18D—C18—H18A	109.5
C8—C9—C10	119.75 (16)	C17—C18—H18B	109.5
C8—C9—H9A	120.1	H18D—C18—H18B	109.5
C10—C9—H9A	120.1	H18A—C18—H18B	109.5
C10—C1—C2—C7	−0.2 (2)	C11—O1—C10—C9	−179.27 (14)
C10—C1—C2—C3	−179.63 (16)	C8—C9—C10—C1	0.7 (3)
C7—C2—C3—C4	−0.7 (3)	C8—C9—C10—O1	−179.89 (15)
C1—C2—C3—C4	178.70 (16)	C10—O1—C11—C12	−175.79 (14)
C2—C3—C4—O3	−178.86 (15)	C13—N1—C12—O2	−1.0 (3)
C2—C3—C4—C5	0.6 (3)	C13—N1—C12—C11	177.16 (16)
O3—C4—C5—C6	179.21 (16)	O1—C11—C12—O2	−167.56 (15)
C3—C4—C5—C6	−0.3 (3)	O1—C11—C12—N1	14.2 (2)
C4—C5—C6—C7	0.1 (3)	C17—N2—C13—C14	−0.6 (3)
C3—C2—C7—C6	0.5 (2)	C17—N2—C13—N1	−179.81 (14)
C1—C2—C7—C6	−178.93 (15)	C12—N1—C13—N2	−178.05 (16)
C3—C2—C7—C8	179.92 (16)	C12—N1—C13—C14	2.7 (3)
C1—C2—C7—C8	0.5 (2)	N2—C13—C14—C15	1.4 (3)
C5—C6—C7—C2	−0.2 (3)	N1—C13—C14—C15	−179.45 (16)
C5—C6—C7—C8	−179.62 (16)	C13—C14—C15—C16	−0.6 (3)
C2—C7—C8—C9	−0.2 (3)	C14—C15—C16—C17	−1.0 (3)
C6—C7—C8—C9	179.21 (16)	C13—N2—C17—C16	−1.1 (2)
C7—C8—C9—C10	−0.4 (3)	C13—N2—C17—C18	176.69 (15)
C2—C1—C10—O1	−179.74 (15)	C15—C16—C17—N2	1.9 (3)
C2—C1—C10—C9	−0.4 (3)	C15—C16—C17—C18	−175.75 (17)
C11—O1—C10—C1	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O3i	0.97	2.45	3.410 (2)	168
N1—H1N1···O1	0.88 (2)	2.11 (2)	2.5688 (18)	111.9 (16)
O3—H1O3···O2ii	0.88 (3)	1.85 (2)	2.6575 (17)	152 (2)
C11—H11A···Cg1iii	0.97	2.63	3.438	141
C18—H18A···Cg2iv	0.97	2.93	3.805	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O3i	0.97	2.45	3.410 (2)	168
N1—H1N1⋯O1	0.88 (2)	2.11 (2)	2.5688 (18)	111.9 (16)
O3—H1O3⋯O2ii	0.88 (3)	1.85 (2)	2.6575 (17)	152 (2)
C11—H11A⋯Cg1iii	0.97	2.63	3.438	141
C18—H18A⋯Cg2iv	0.97	2.92	3.805	153

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C1,C2,C7–C10 ring and Cg2 is the centroid of C2–C7 ring.