2-Hy-droxy-N'-[2-(6-meth-oxy-naphthalen-2-yl)propano-yl]benzohydrazide.

In the title compound, C(21)H(20)N(2)O(4), the naphthalene ring system makes a dihedral angle of 84.5 (3)° with the benzene ring, and the -C(=O)-N(H)-N(H)-C(=O)- torsion angle is 70.7 (7)°, so that the mol-ecule is twisted. An S(6) ring motif is formed via an intra-molecular O-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds into supra-molecular layers in the ab plane.

Related literature

For the pharmaceutical applications of naproxen [systematic name: (+)-6-meth­oxy-α-methyl-2-naphthalene acetic acid], see: Teplyakov et al. (1993 ▶); Bozdag et al. (2001 ▶). For the synthesis of potential biologically active compounds based on the structure of naproxen, see: Sharma et al. (2003 ▶); Kumar et al. (2010 ▶). For related structures, see: Yathirajan et al. (2007 ▶); Liang et al. (2008 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C21H20N2O4

M = 364.39

Orthorhombic,

a = 4.851 (6) Å

b = 10.407 (12) Å

c = 36.65 (4) Å

V = 1850 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.14 × 0.05 × 0.01 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011 ▶) T min = 0.987, T max = 0.999

5963 measured reflections

2303 independent reflections

1169 reflections with I > 2σ(I)

R int = 0.102

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.189

S = 1.09

2303 reflections

257 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2011 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012731/tk5071sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012731/tk5071Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012731/tk5071Isup3.cml

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

C21H20N2O4	F(000) = 768
Mr = 364.39	Dx = 1.308 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4928 reflections
a = 4.851 (6) Å	θ = 2.0–30.1°
b = 10.407 (12) Å	µ = 0.09 mm−1
c = 36.65 (4) Å	T = 100 K
V = 1850 (4) Å3	Sheet, colourless
Z = 4	0.14 × 0.05 × 0.01 mm

Rigaku Saturn724+ diffractometer	2303 independent reflections
Radiation source: Rotating Anode	1169 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.102
Detector resolution: 28.5714 pixels mm-1	θmax = 27.3°, θmin = 2.6°
profile data from ω–scans	h = −6→4
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011)	k = −13→12
Tmin = 0.987, Tmax = 0.999	l = −47→23
5963 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.084	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.189	w = 1/[σ2(Fo2) + (0.0587P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2303 reflections	Δρmax = 0.30 e Å−3
257 parameters	Δρmin = −0.24 e Å−3
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

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	0.5719 (10)	−0.0932 (4)	0.02322 (12)	0.0513 (17)
O2	0.8625 (10)	0.5761 (4)	0.16863 (13)	0.0427 (17)
O3	0.5850 (8)	0.7217 (4)	0.23922 (11)	0.0353 (16)
O4	0.9808 (11)	0.8058 (4)	0.28151 (13)	0.0387 (16)
N1	0.4392 (11)	0.5286 (5)	0.19267 (15)	0.0303 (17)
N2	0.5549 (11)	0.5038 (5)	0.22776 (15)	0.0337 (17)
C1	0.6354 (15)	0.2465 (7)	0.05874 (18)	0.044 (3)
C2	0.7799 (17)	0.3603 (8)	0.0541 (2)	0.063 (3)
C3	0.7265 (17)	0.4677 (7)	0.07585 (19)	0.055 (3)
C4	0.5185 (14)	0.4648 (6)	0.10359 (18)	0.038 (3)
C5	0.3727 (14)	0.3541 (6)	0.10912 (18)	0.043 (3)
C6	0.4279 (15)	0.2393 (6)	0.08636 (17)	0.040 (3)
C7	0.2788 (17)	0.1242 (7)	0.09106 (19)	0.056 (3)
C8	0.3346 (17)	0.0178 (7)	0.06947 (19)	0.055 (3)
C9	0.5405 (17)	0.0239 (7)	0.04166 (19)	0.048 (3)
C10	0.6932 (17)	0.1321 (7)	0.03550 (19)	0.056 (3)
C11	0.7870 (15)	−0.1005 (7)	−0.00403 (19)	0.058 (3)
C12	0.4624 (13)	0.5834 (6)	0.12777 (16)	0.034 (2)
C13	0.5530 (16)	0.7139 (6)	0.11123 (16)	0.046 (3)
C14	0.6096 (15)	0.5647 (6)	0.16510 (18)	0.032 (2)
C15	0.6505 (12)	0.6079 (6)	0.24718 (17)	0.032 (2)
C16	0.8385 (13)	0.5788 (6)	0.27894 (16)	0.0300 (19)
C17	0.9991 (13)	0.6797 (6)	0.29347 (17)	0.032 (2)
C18	1.1903 (13)	0.6545 (6)	0.32135 (17)	0.036 (2)
C19	1.2169 (14)	0.5287 (6)	0.33541 (16)	0.035 (2)
C20	1.0521 (13)	0.4295 (6)	0.32161 (17)	0.037 (2)
C21	0.8645 (14)	0.4527 (6)	0.29390 (16)	0.033 (2)
H1N	0.260 (5)	0.521 (6)	0.1924 (14)	0.027 (18)*
H2	0.91480	0.36530	0.03610	0.0750*
H2N	0.636 (12)	0.431 (4)	0.2295 (18)	0.06 (3)*
H3	0.82790	0.54250	0.07230	0.0660*
H4	0.851 (9)	0.797 (6)	0.2673 (14)	0.05 (3)*
H5	0.23850	0.35090	0.12720	0.0520*
H7	0.14190	0.11960	0.10880	0.0670*
H8	0.23720	−0.05810	0.07310	0.0660*
H10	0.82820	0.13420	0.01750	0.0660*
H11A	0.78710	−0.18460	−0.01480	0.0870*
H11B	0.96250	−0.08480	0.00720	0.0870*
H11C	0.75440	−0.03720	−0.02260	0.0870*
H12	0.26350	0.58760	0.13230	0.0410*
H13A	0.50790	0.78200	0.12790	0.0700*
H13B	0.45870	0.72750	0.08850	0.0700*
H13C	0.74830	0.71300	0.10710	0.0700*
H18	1.29920	0.72050	0.33050	0.0430*
H19	1.34370	0.51170	0.35380	0.0420*
H20	1.06880	0.34700	0.33120	0.0440*
H21	0.75540	0.38620	0.28500	0.0390*

	U11	U22	U33	U12	U13	U23
O1	0.062 (3)	0.038 (3)	0.054 (3)	0.003 (3)	−0.002 (3)	−0.010 (2)
O2	0.022 (3)	0.046 (3)	0.060 (3)	0.000 (2)	−0.006 (2)	0.003 (3)
O3	0.034 (3)	0.022 (2)	0.050 (3)	0.006 (2)	−0.002 (2)	0.004 (2)
O4	0.043 (3)	0.021 (2)	0.052 (3)	−0.006 (2)	−0.008 (3)	−0.003 (2)
N1	0.016 (3)	0.029 (3)	0.046 (3)	0.003 (3)	−0.003 (3)	0.001 (3)
N2	0.032 (3)	0.026 (3)	0.043 (3)	−0.004 (3)	−0.011 (3)	−0.001 (3)
C1	0.034 (4)	0.048 (5)	0.049 (4)	−0.002 (4)	−0.010 (4)	0.004 (4)
C2	0.050 (5)	0.064 (6)	0.074 (6)	0.001 (5)	0.011 (5)	0.002 (5)
C3	0.054 (5)	0.052 (5)	0.058 (5)	0.005 (5)	0.009 (5)	−0.016 (4)
C4	0.037 (5)	0.027 (4)	0.049 (4)	0.004 (4)	−0.004 (4)	−0.004 (3)
C5	0.044 (5)	0.035 (4)	0.051 (4)	0.011 (4)	−0.007 (4)	−0.008 (3)
C6	0.043 (5)	0.041 (4)	0.037 (4)	−0.005 (4)	−0.015 (3)	0.009 (3)
C7	0.063 (6)	0.045 (5)	0.060 (5)	−0.002 (5)	−0.006 (5)	−0.003 (4)
C8	0.076 (6)	0.046 (5)	0.044 (4)	0.021 (5)	−0.021 (5)	−0.009 (4)
C9	0.057 (6)	0.039 (4)	0.049 (4)	0.012 (5)	−0.016 (4)	−0.013 (4)
C10	0.061 (5)	0.050 (5)	0.056 (5)	0.009 (5)	−0.015 (4)	−0.019 (4)
C11	0.058 (5)	0.051 (5)	0.065 (5)	−0.002 (5)	−0.005 (5)	−0.008 (4)
C12	0.024 (4)	0.034 (4)	0.045 (4)	0.002 (3)	−0.004 (3)	−0.005 (3)
C13	0.064 (5)	0.038 (4)	0.037 (4)	−0.001 (4)	−0.008 (4)	0.005 (3)
C14	0.038 (5)	0.015 (3)	0.044 (4)	0.001 (3)	−0.001 (4)	0.000 (3)
C15	0.024 (4)	0.033 (4)	0.038 (4)	0.003 (4)	0.006 (3)	0.002 (3)
C16	0.031 (4)	0.021 (3)	0.038 (3)	−0.002 (3)	0.006 (3)	−0.011 (3)
C17	0.034 (4)	0.021 (3)	0.041 (4)	0.007 (3)	0.014 (3)	0.001 (3)
C18	0.033 (4)	0.024 (4)	0.051 (4)	−0.004 (3)	−0.010 (4)	−0.005 (3)
C19	0.031 (4)	0.038 (4)	0.036 (4)	0.002 (4)	−0.001 (3)	0.002 (3)
C20	0.041 (4)	0.027 (4)	0.042 (4)	0.001 (4)	−0.004 (4)	−0.003 (3)
C21	0.033 (4)	0.024 (4)	0.041 (4)	0.001 (3)	0.003 (3)	0.000 (3)

O1—C9	1.402 (9)	C15—C16	1.509 (9)
O1—C11	1.446 (9)	C16—C21	1.428 (9)
O2—C14	1.239 (9)	C16—C17	1.412 (9)
O3—C15	1.260 (8)	C17—C18	1.405 (9)
O4—C17	1.386 (8)	C18—C19	1.413 (9)
O4—H4	0.82 (5)	C19—C20	1.400 (9)
N1—N2	1.427 (8)	C20—C21	1.385 (9)
N1—C14	1.359 (9)	C2—H2	0.9300
N2—C15	1.377 (8)	C3—H3	0.9300
N1—H1N	0.87 (3)	C5—H5	0.9300
N2—H2N	0.86 (5)	C7—H7	0.9300
C1—C10	1.491 (10)	C8—H8	0.9300
C1—C2	1.387 (11)	C10—H10	0.9300
C1—C6	1.430 (10)	C11—H11A	0.9600
C2—C3	1.397 (11)	C11—H11B	0.9600
C3—C4	1.433 (10)	C11—H11C	0.9600
C4—C5	1.367 (9)	C12—H12	0.9800
C4—C12	1.544 (9)	C13—H13A	0.9600
C5—C6	1.482 (9)	C13—H13B	0.9600
C6—C7	1.410 (10)	C13—H13C	0.9600
C7—C8	1.388 (10)	C18—H18	0.9300
C8—C9	1.429 (11)	C19—H19	0.9300
C9—C10	1.367 (11)	C20—H20	0.9300
C12—C13	1.551 (9)	C21—H21	0.9300
C12—C14	1.556 (9)
C9—O1—C11	117.2 (5)	O4—C17—C16	123.3 (6)
C17—O4—H4	98 (4)	C17—C18—C19	119.9 (6)
N2—N1—C14	118.8 (5)	C18—C19—C20	120.0 (6)
N1—N2—C15	117.1 (5)	C19—C20—C21	120.8 (6)
C14—N1—H1N	129 (4)	C16—C21—C20	120.0 (6)
N2—N1—H1N	113 (3)	C1—C2—H2	119.00
N1—N2—H2N	114 (4)	C3—C2—H2	119.00
C15—N2—H2N	120 (4)	C2—C3—H3	119.00
C2—C1—C6	119.2 (6)	C4—C3—H3	119.00
C2—C1—C10	121.1 (7)	C4—C5—H5	120.00
C6—C1—C10	119.7 (6)	C6—C5—H5	120.00
C1—C2—C3	121.3 (7)	C6—C7—H7	120.00
C2—C3—C4	121.2 (7)	C8—C7—H7	120.00
C3—C4—C5	119.2 (6)	C7—C8—H8	120.00
C3—C4—C12	121.0 (6)	C9—C8—H8	120.00
C5—C4—C12	119.8 (6)	C1—C10—H10	121.00
C4—C5—C6	120.2 (6)	C9—C10—H10	121.00
C5—C6—C7	121.6 (6)	O1—C11—H11A	109.00
C1—C6—C7	119.5 (6)	O1—C11—H11B	110.00
C1—C6—C5	118.9 (6)	O1—C11—H11C	110.00
C6—C7—C8	120.6 (7)	H11A—C11—H11B	109.00
C7—C8—C9	120.5 (7)	H11A—C11—H11C	110.00
O1—C9—C8	112.4 (6)	H11B—C11—H11C	109.00
C8—C9—C10	122.2 (7)	C4—C12—H12	108.00
O1—C9—C10	125.3 (7)	C13—C12—H12	108.00
C1—C10—C9	117.5 (7)	C14—C12—H12	108.00
C13—C12—C14	108.9 (5)	C12—C13—H13A	109.00
C4—C12—C13	115.2 (5)	C12—C13—H13B	109.00
C4—C12—C14	108.9 (5)	C12—C13—H13C	109.00
O2—C14—N1	123.5 (6)	H13A—C13—H13B	110.00
O2—C14—C12	122.3 (6)	H13A—C13—H13C	109.00
N1—C14—C12	114.2 (6)	H13B—C13—H13C	110.00
O3—C15—N2	122.3 (5)	C17—C18—H18	120.00
N2—C15—C16	116.4 (5)	C19—C18—H18	120.00
O3—C15—C16	121.3 (5)	C18—C19—H19	120.00
C15—C16—C21	122.3 (5)	C20—C19—H19	120.00
C17—C16—C21	119.3 (6)	C19—C20—H20	120.00
C15—C16—C17	118.4 (5)	C21—C20—H20	120.00
O4—C17—C18	116.7 (5)	C16—C21—H21	120.00
C16—C17—C18	120.0 (6)	C20—C21—H21	120.00
C11—O1—C9—C8	−176.3 (6)	C5—C6—C7—C8	−179.9 (7)
C11—O1—C9—C10	1.3 (10)	C1—C6—C7—C8	0.9 (11)
N2—N1—C14—O2	0.8 (9)	C6—C7—C8—C9	−1.2 (11)
C14—N1—N2—C15	70.7 (7)	C7—C8—C9—O1	178.8 (7)
N2—N1—C14—C12	177.5 (5)	C7—C8—C9—C10	1.2 (12)
N1—N2—C15—C16	−164.0 (5)	O1—C9—C10—C1	−178.1 (6)
N1—N2—C15—O3	16.3 (8)	C8—C9—C10—C1	−0.8 (11)
C10—C1—C6—C7	−0.5 (10)	C4—C12—C14—N1	−102.1 (6)
C6—C1—C2—C3	0.0 (11)	C13—C12—C14—O2	−51.7 (8)
C2—C1—C6—C5	0.3 (10)	C13—C12—C14—N1	131.6 (6)
C2—C1—C10—C9	−179.6 (7)	C4—C12—C14—O2	74.7 (7)
C6—C1—C10—C9	0.5 (10)	O3—C15—C16—C17	−17.0 (9)
C10—C1—C2—C3	−179.9 (7)	O3—C15—C16—C21	164.9 (6)
C2—C1—C6—C7	179.6 (7)	N2—C15—C16—C17	163.3 (6)
C10—C1—C6—C5	−179.8 (6)	N2—C15—C16—C21	−14.9 (9)
C1—C2—C3—C4	−0.6 (12)	C15—C16—C17—O4	4.0 (9)
C2—C3—C4—C12	179.4 (7)	C15—C16—C17—C18	−175.6 (6)
C2—C3—C4—C5	0.9 (11)	C21—C16—C17—O4	−177.8 (6)
C5—C4—C12—C14	78.8 (7)	C21—C16—C17—C18	2.6 (9)
C3—C4—C12—C14	−99.7 (7)	C15—C16—C21—C20	176.1 (6)
C12—C4—C5—C6	−179.2 (6)	C17—C16—C21—C20	−2.0 (9)
C3—C4—C12—C13	22.9 (9)	O4—C17—C18—C19	178.8 (6)
C5—C4—C12—C13	−158.6 (6)	C16—C17—C18—C19	−1.5 (9)
C3—C4—C5—C6	−0.7 (10)	C17—C18—C19—C20	−0.2 (9)
C4—C5—C6—C7	−179.2 (7)	C18—C19—C20—C21	0.8 (9)
C4—C5—C6—C1	0.1 (10)	C19—C20—C21—C16	0.3 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.87 (3)	2.19 (3)	2.974 (8)	149 (5)
N2—H2N···O4ii	0.86 (5)	2.31 (5)	3.072 (8)	149 (5)
O4—H4···O3	0.82 (5)	1.83 (5)	2.618 (7)	161 (6)
C12—H12···O2i	0.98	2.36	3.274 (9)	155
C21—H21···O3iii	0.93	2.54	3.465 (9)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.87 (3)	2.19 (3)	2.974 (8)	149 (5)
N2—H2N⋯O4ii	0.86 (5)	2.31 (5)	3.072 (8)	149 (5)
O4—H4⋯O3	0.82 (5)	1.83 (5)	2.618 (7)	161 (6)
C12—H12⋯O2i	0.98	2.36	3.274 (9)	155
C21—H21⋯O3iii	0.93	2.54	3.465 (9)	174

Symmetry codes: (i) ; (ii) ; (iii) .