N-[(2-Hydr-oxy-1-naphthyl)(3-nitro-phenyl)meth-yl]acetamide.

The title compound, C(19)H(16)N(2)O(4), is of inter-est as a precursor to biologically active substituted quinolines and related compounds. The dihedral angle between the naphthalene ring system and the benzene ring is 81.9 (1)°. The crystal structure is stabilized by N-H⋯O inter-molecular hydrogen bonds, linking the mol-ecules into pairs around a center of symmetry. The crystal structure is further stabilized by inter-molecular O-H⋯O hydrogen bonds, which link the mol-ecules into chains running along a axis. An intra-molecular C-H⋯O short contact is also present.

Related literature

For N-(substituted phen­yl)acetamides as precursors for the synthesis of hetrocyclic compounds, see: Wen et al. (2005 ▶, 2006 ▶). For multicomponent reactions, see: Devi & Bhuyan (2004 ▶); Domling & Ugi (2000 ▶). For the properties and potential applications of amide-type compounds and their metal ion complexes, see: Saravanakumar et al. (2005 ▶); Yin et al. (2004 ▶). For related structures, see: Mosslemin et al. (2007 ▶); Zia-ur-Rehman et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶); Liu & Li (2004 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H16N2O4

M = 336.34

Triclinic,

a = 7.5261 (4) Å

b = 8.8635 (5) Å

c = 13.3008 (7) Å

α = 74.720 (3)°

β = 73.754 (3)°

γ = 82.600 (3)°

V = 820.27 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.4 × 0.2 × 0.1 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.974, T max = 0.990

9406 measured reflections

3864 independent reflections

2227 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.144

S = 0.99

3864 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009)’.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007442/jh2076sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007442/jh2076Isup2.hkl

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

C19H16N2O4	Z = 2
Mr = 336.34	F(000) = 352
Triclinic, P1	Dx = 1.362 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5261 (4) Å	Cell parameters from 3864 reflections
b = 8.8635 (5) Å	θ = 2.5–25°
c = 13.3008 (7) Å	µ = 0.10 mm−1
α = 74.720 (3)°	T = 293 K
β = 73.754 (3)°	Needle, colourless
γ = 82.600 (3)°	0.4 × 0.2 × 0.1 mm
V = 820.27 (14) Å3

Bruker Kappa APEXII CCD diffractometer	3864 independent reflections
Radiation source: fine-focus sealed tube	2227 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω and φ scan	θmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→10
Tmin = 0.974, Tmax = 0.990	k = −11→11
9406 measured reflections	l = −17→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0612P)2 + 0.220P] where P = (Fo2 + 2Fc2)/3
3864 reflections	(Δ/σ)max = 0.009
227 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. 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.

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 > σ(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	1.11375 (16)	0.78003 (16)	0.26550 (11)	0.0490 (4)
H1	1.2259	0.7587	0.2525	0.074*
O2	0.9758 (4)	0.5649 (2)	0.62604 (17)	0.1025 (7)
O3	0.8781 (4)	0.6954 (3)	0.74538 (16)	0.1150 (8)
O4	0.46636 (19)	0.7392 (2)	0.26984 (17)	0.0801 (6)
N1	0.74868 (19)	0.71417 (18)	0.29573 (12)	0.0401 (4)
H1A	0.8443	0.6528	0.3045	0.048*
N2	0.8965 (3)	0.6794 (3)	0.65559 (16)	0.0667 (5)
C1	1.0777 (2)	0.9135 (2)	0.19395 (14)	0.0385 (4)
C2	1.2195 (2)	0.9945 (3)	0.11175 (16)	0.0502 (5)
H2	1.3425	0.9575	0.1056	0.060*
C3	1.1769 (3)	1.1262 (3)	0.04174 (17)	0.0536 (5)
H3	1.2720	1.1793	−0.0117	0.064*
C4	0.9922 (3)	1.1848 (2)	0.04788 (15)	0.0473 (5)
C5	0.9457 (4)	1.3208 (3)	−0.02594 (17)	0.0632 (6)
H5	1.0402	1.3758	−0.0786	0.076*
C6	0.7679 (4)	1.3729 (3)	−0.0220 (2)	0.0732 (7)
H6	0.7408	1.4619	−0.0721	0.088*
C7	0.6253 (4)	1.2929 (3)	0.05736 (19)	0.0634 (6)
H7	0.5029	1.3285	0.0595	0.076*
C8	0.6626 (3)	1.1628 (2)	0.13215 (17)	0.0495 (5)
H8	0.5649	1.1126	0.1852	0.059*
C9	0.8474 (2)	1.1027 (2)	0.13058 (14)	0.0384 (4)
C10	0.8943 (2)	0.9665 (2)	0.20492 (14)	0.0353 (4)
C11	0.7483 (2)	0.8774 (2)	0.29803 (14)	0.0356 (4)
H11	0.6276	0.9264	0.2889	0.043*
C12	0.7637 (2)	0.8970 (2)	0.40573 (14)	0.0366 (4)
C13	0.7214 (2)	1.0446 (2)	0.42690 (16)	0.0448 (5)
H13	0.6865	1.1272	0.3751	0.054*
C14	0.7299 (3)	1.0718 (3)	0.52306 (17)	0.0508 (5)
H14	0.6998	1.1715	0.5356	0.061*
C15	0.7827 (3)	0.9515 (3)	0.60021 (16)	0.0500 (5)
H15	0.7880	0.9677	0.6656	0.060*
C16	0.8275 (3)	0.8069 (2)	0.57761 (15)	0.0452 (5)
C17	0.8192 (2)	0.7764 (2)	0.48202 (14)	0.0411 (4)
H17	0.8504	0.6766	0.4697	0.049*
C18	0.6061 (2)	0.6567 (2)	0.28056 (16)	0.0457 (5)
C19	0.6235 (3)	0.4876 (3)	0.2787 (2)	0.0719 (7)
H19A	0.5450	0.4293	0.3438	0.108*
H19B	0.7499	0.4483	0.2734	0.108*
H19C	0.5866	0.4764	0.2176	0.108*

	U11	U22	U33	U12	U13	U23
O1	0.0284 (6)	0.0571 (9)	0.0628 (9)	0.0062 (6)	−0.0192 (6)	−0.0126 (7)
O2	0.163 (2)	0.0682 (13)	0.0971 (15)	0.0310 (13)	−0.0825 (15)	−0.0215 (12)
O3	0.189 (3)	0.1062 (17)	0.0557 (12)	0.0012 (16)	−0.0525 (14)	−0.0122 (11)
O4	0.0403 (8)	0.0771 (12)	0.1474 (17)	0.0087 (8)	−0.0497 (10)	−0.0471 (12)
N1	0.0309 (7)	0.0380 (9)	0.0574 (9)	0.0045 (6)	−0.0211 (7)	−0.0146 (7)
N2	0.0861 (14)	0.0639 (14)	0.0559 (12)	−0.0130 (11)	−0.0321 (10)	−0.0056 (11)
C1	0.0318 (8)	0.0457 (11)	0.0440 (10)	0.0000 (8)	−0.0138 (7)	−0.0177 (9)
C2	0.0313 (9)	0.0701 (14)	0.0556 (12)	−0.0066 (9)	−0.0079 (8)	−0.0277 (11)
C3	0.0516 (12)	0.0623 (14)	0.0462 (11)	−0.0172 (10)	−0.0023 (9)	−0.0161 (11)
C4	0.0581 (12)	0.0454 (12)	0.0416 (10)	−0.0068 (9)	−0.0100 (9)	−0.0170 (9)
C5	0.0878 (18)	0.0488 (13)	0.0467 (12)	−0.0081 (12)	−0.0087 (12)	−0.0080 (11)
C6	0.104 (2)	0.0478 (14)	0.0603 (15)	0.0171 (14)	−0.0250 (14)	−0.0070 (12)
C7	0.0736 (15)	0.0513 (13)	0.0669 (15)	0.0205 (12)	−0.0295 (12)	−0.0161 (12)
C8	0.0502 (11)	0.0455 (12)	0.0554 (12)	0.0086 (9)	−0.0204 (9)	−0.0145 (10)
C9	0.0424 (9)	0.0368 (10)	0.0410 (10)	0.0010 (8)	−0.0135 (8)	−0.0162 (8)
C10	0.0314 (8)	0.0386 (10)	0.0418 (10)	−0.0003 (7)	−0.0128 (7)	−0.0165 (8)
C11	0.0268 (8)	0.0343 (10)	0.0496 (10)	0.0039 (7)	−0.0154 (7)	−0.0131 (8)
C12	0.0238 (7)	0.0404 (10)	0.0462 (10)	−0.0016 (7)	−0.0079 (7)	−0.0126 (8)
C13	0.0374 (9)	0.0424 (11)	0.0554 (12)	0.0021 (8)	−0.0107 (8)	−0.0162 (9)
C14	0.0437 (10)	0.0500 (12)	0.0622 (13)	−0.0030 (9)	−0.0055 (9)	−0.0280 (11)
C15	0.0436 (10)	0.0636 (14)	0.0466 (11)	−0.0122 (10)	−0.0046 (9)	−0.0229 (11)
C16	0.0413 (10)	0.0504 (12)	0.0440 (11)	−0.0097 (9)	−0.0106 (8)	−0.0084 (9)
C17	0.0389 (9)	0.0405 (11)	0.0468 (11)	−0.0037 (8)	−0.0121 (8)	−0.0133 (9)
C18	0.0350 (9)	0.0511 (12)	0.0568 (12)	−0.0047 (8)	−0.0161 (8)	−0.0175 (10)
C19	0.0677 (15)	0.0586 (15)	0.103 (2)	−0.0135 (12)	−0.0270 (14)	−0.0323 (15)

O1—C1	1.359 (2)	C7—H7	0.9300
O1—H1	0.8200	C8—C9	1.420 (3)
O2—N2	1.209 (3)	C8—H8	0.9300
O3—N2	1.207 (3)	C9—C10	1.420 (2)
O4—C18	1.222 (2)	C10—C11	1.520 (2)
N1—C18	1.329 (2)	C11—C12	1.525 (2)
N1—C11	1.455 (2)	C11—H11	0.9800
N1—H1A	0.8600	C12—C17	1.378 (2)
N2—C16	1.468 (3)	C12—C13	1.389 (3)
C1—C10	1.380 (2)	C13—C14	1.382 (3)
C1—C2	1.407 (3)	C13—H13	0.9300
C2—C3	1.353 (3)	C14—C15	1.375 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.408 (3)	C15—C16	1.372 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.414 (3)	C16—C17	1.387 (3)
C4—C9	1.428 (3)	C17—H17	0.9300
C5—C6	1.349 (3)	C18—O4	1.222 (2)
C5—H5	0.9300	C18—C19	1.494 (3)
C6—C7	1.391 (4)	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C7—C8	1.366 (3)	C19—H19C	0.9600
C1—O1—H1	109.5	C9—C10—C11	121.98 (14)
C18—N1—C11	122.19 (15)	N1—C11—C10	112.60 (14)
C18—N1—H1A	118.9	N1—C11—C12	112.92 (14)
C11—N1—H1A	118.9	C10—C11—C12	111.04 (13)
O3—N2—O2	122.6 (2)	N1—C11—H11	106.6
O3—N2—C16	118.8 (2)	C10—C11—H11	106.6
O2—N2—C16	118.6 (2)	C12—C11—H11	106.6
O1—C1—C10	116.89 (16)	C17—C12—C13	118.70 (17)
O1—C1—C2	122.07 (15)	C17—C12—C11	123.28 (16)
C10—C1—C2	121.03 (17)	C13—C12—C11	118.02 (16)
C3—C2—C1	120.01 (18)	C14—C13—C12	121.61 (19)
C3—C2—H2	120.0	C14—C13—H13	119.2
C1—C2—H2	120.0	C12—C13—H13	119.2
C2—C3—C4	121.59 (19)	C15—C14—C13	120.02 (19)
C2—C3—H3	119.2	C15—C14—H14	120.0
C4—C3—H3	119.2	C13—C14—H14	120.0
C3—C4—C5	122.1 (2)	C16—C15—C14	117.86 (18)
C3—C4—C9	118.75 (18)	C16—C15—H15	121.1
C5—C4—C9	119.13 (19)	C14—C15—H15	121.1
C6—C5—C4	121.8 (2)	C15—C16—C17	123.22 (19)
C6—C5—H5	119.1	C15—C16—N2	118.79 (18)
C4—C5—H5	119.1	C17—C16—N2	117.91 (19)
C5—C6—C7	119.7 (2)	C12—C17—C16	118.56 (18)
C5—C6—H6	120.2	C12—C17—H17	120.7
C7—C6—H6	120.2	C16—C17—H17	120.7
C8—C7—C6	121.0 (2)	O4—C18—N1	120.94 (18)
C8—C7—H7	119.5	O4—C18—N1	120.94 (18)
C6—C7—H7	119.5	O4—C18—C19	121.76 (18)
C7—C8—C9	121.4 (2)	O4—C18—C19	121.76 (18)
C7—C8—H8	119.3	N1—C18—C19	117.29 (17)
C9—C8—H8	119.3	C18—C19—H19A	109.5
C10—C9—C8	123.85 (17)	C18—C19—H19B	109.5
C10—C9—C4	119.07 (16)	H19A—C19—H19B	109.5
C8—C9—C4	117.07 (17)	C18—C19—H19C	109.5
C1—C10—C9	119.52 (16)	H19A—C19—H19C	109.5
C1—C10—C11	118.50 (15)	H19B—C19—H19C	109.5
O1—C1—C2—C3	179.40 (18)	C1—C10—C11—N1	−58.74 (19)
C10—C1—C2—C3	−0.2 (3)	C9—C10—C11—N1	122.18 (17)
C1—C2—C3—C4	−0.7 (3)	C1—C10—C11—C12	69.00 (19)
C2—C3—C4—C5	−178.9 (2)	C9—C10—C11—C12	−110.08 (17)
C2—C3—C4—C9	0.3 (3)	N1—C11—C12—C17	15.6 (2)
C3—C4—C5—C6	177.5 (2)	C10—C11—C12—C17	−111.95 (18)
C9—C4—C5—C6	−1.7 (3)	N1—C11—C12—C13	−165.13 (14)
C4—C5—C6—C7	0.9 (4)	C10—C11—C12—C13	67.30 (18)
C5—C6—C7—C8	0.6 (4)	C17—C12—C13—C14	−1.4 (3)
C6—C7—C8—C9	−1.2 (3)	C11—C12—C13—C14	179.28 (16)
C7—C8—C9—C10	−178.80 (19)	C12—C13—C14—C15	0.6 (3)
C7—C8—C9—C4	0.4 (3)	C13—C14—C15—C16	0.6 (3)
C3—C4—C9—C10	1.0 (3)	C14—C15—C16—C17	−1.0 (3)
C5—C4—C9—C10	−179.76 (18)	C14—C15—C16—N2	175.85 (18)
C3—C4—C9—C8	−178.19 (18)	O3—N2—C16—C15	14.4 (3)
C5—C4—C9—C8	1.0 (3)	O2—N2—C16—C15	−162.9 (2)
O1—C1—C10—C9	−178.11 (15)	O3—N2—C16—C17	−168.6 (2)
C2—C1—C10—C9	1.5 (3)	O2—N2—C16—C17	14.1 (3)
O1—C1—C10—C11	2.8 (2)	C13—C12—C17—C16	1.1 (2)
C2—C1—C10—C11	−177.60 (16)	C11—C12—C17—C16	−179.69 (16)
C8—C9—C10—C1	177.26 (17)	C15—C16—C17—C12	0.1 (3)
C4—C9—C10—C1	−1.9 (2)	N2—C16—C17—C12	−176.74 (16)
C8—C9—C10—C11	−3.7 (3)	C11—N1—C18—O4	−1.4 (3)
C4—C9—C10—C11	177.17 (16)	C11—N1—C18—O4	−1.4 (3)
C18—N1—C11—C10	−114.89 (18)	C11—N1—C18—C19	179.39 (19)
C18—N1—C11—C12	118.37 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.82	1.87	2.646 (2)	158
N1—H1A···O2ii	0.86	2.35	3.167 (2)	160
C11—H11···O4	0.98	2.28	2.739 (2)	107

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.82	1.87	2.646 (2)	158
N1—H1A⋯O2ii	0.86	2.35	3.167 (2)	160
C11—H11⋯O4	0.98	2.28	2.739 (2)	107

Symmetry codes: (i) ; (ii) .