2-Hydro­xy­aceto­phenone 3-hydroxy-2-naphthoyl­hydrazone

The molecule of the title compound, C₁₉H₁₅N₂O₃, an aroyl­hydrazone, is almost planar. The C=O bond length of 1.219 (2) Å suggests that the title compound is in the keto form. The C=N double bond has a length of 1.280 (2) Å. The crystal structure is stabilized by N—H...O, O—H...O and O—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.137
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-Hydroxyacetophenone 3-hydroxy-2-naphthoylhydrazone

Crystal data

C19H16N2O3	F(000) = 672
Mr = 320.34	Dx = 1.372 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1742 reflections
a = 8.6329 (12) Å	θ = 2.4–25.5°
b = 8.0641 (11) Å	µ = 0.09 mm^−1
c = 22.621 (3) Å	T = 273 K
β = 99.920 (3)°	Plate, light yellow
V = 1551.2 (4) Å^3	0.25 × 0.2 × 0.2 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2226 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.026
Graphite monochromator	θmax = 26.0°, θmin = 2.7°
φ and ω scans	h = −10→7
8027 measured reflections	k = −9→9
3039 independent reflections	l = −27→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0635P)^2 + 0.3335P] where P = (Fo^2 + 2Fc^2)/3
3039 reflections	(Δ/σ)max = 0.038
220 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Experimental. FT–IR spectra were measured by a Nicolet AVATAR 360. Elemental analyses were performed on a Varian EL elemental analyser.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2747 (2)	0.5413 (2)	0.10565 (7)	0.0379 (4)
C2	0.2867 (2)	0.4590 (2)	0.15912 (8)	0.0450 (5)
H2	0.1953	0.4405	0.1747	0.054*
C3	0.4295 (2)	0.4012 (2)	0.19158 (8)	0.0451 (5)
C4	0.4407 (3)	0.3144 (3)	0.24646 (9)	0.0603 (6)
H4	0.3504	0.2950	0.2626	0.072*
C5	0.5813 (3)	0.2588 (3)	0.27585 (9)	0.0671 (7)
H5	0.5871	0.2033	0.3122	0.081*
C6	0.7179 (3)	0.2850 (3)	0.25156 (9)	0.0630 (6)
H6	0.8136	0.2446	0.2715	0.076*
C7	0.7123 (3)	0.3684 (2)	0.19944 (9)	0.0526 (5)
H7	0.8045	0.3857	0.1843	0.063*
C8	0.5686 (2)	0.4295 (2)	0.16761 (8)	0.0424 (5)
C9	0.5573 (2)	0.5147 (2)	0.11295 (8)	0.0429 (5)
H9	0.6481	0.5347	0.0972	0.051*
C10	0.4161 (2)	0.5690 (2)	0.08241 (7)	0.0383 (4)
C11	0.1138 (2)	0.5967 (2)	0.07701 (8)	0.0407 (4)
C12	−0.0456 (2)	0.8305 (2)	−0.05001 (8)	0.0403 (4)
C13	−0.2029 (2)	0.8935 (2)	−0.07529 (8)	0.0388 (4)
C14	−0.2299 (2)	0.9881 (3)	−0.12736 (9)	0.0517 (5)
H14	−0.1455	1.0137	−0.1463	0.062*
C15	−0.3766 (2)	1.0448 (3)	−0.15175 (9)	0.0569 (6)
H15	−0.3910	1.1069	−0.1869	0.068*
C16	−0.5023 (2)	1.0097 (3)	−0.12403 (10)	0.0559 (5)
H16	−0.6022	1.0477	−0.1404	0.067*
C17	−0.4800 (2)	0.9188 (3)	−0.07241 (9)	0.0510 (5)
H17	−0.5653	0.8964	−0.0535	0.061*
C18	−0.3328 (2)	0.8593 (2)	−0.04764 (8)	0.0388 (4)
C19	0.0917 (2)	0.8626 (3)	−0.08064 (10)	0.0627 (6)
H19A	0.1588	0.9444	−0.0585	0.094*
H19B	0.0548	0.9023	−0.1206	0.094*
H19C	0.1496	0.7616	−0.0825	0.094*
N1	0.10555 (16)	0.6850 (2)	0.02567 (7)	0.0439 (4)
H1A	0.1886	0.7015	0.0102	0.053*
N2	−0.03579 (16)	0.74735 (19)	−0.00129 (7)	0.0415 (4)
O1	0.40652 (14)	0.64891 (18)	0.02900 (5)	0.0490 (4)
H1	0.4953	0.6700	0.0229	0.074*
O2	−0.00282 (15)	0.56556 (19)	0.09862 (6)	0.0570 (4)
O3	−0.32152 (14)	0.76911 (18)	0.00346 (6)	0.0507 (4)
H3	−0.2306	0.7376	0.0137	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0399 (10)	0.0384 (10)	0.0371 (9)	−0.0020 (8)	0.0118 (8)	−0.0039 (8)
C2	0.0500 (11)	0.0460 (11)	0.0428 (10)	−0.0026 (9)	0.0187 (9)	−0.0018 (9)
C3	0.0588 (12)	0.0413 (11)	0.0356 (9)	0.0023 (9)	0.0096 (9)	−0.0032 (8)
C4	0.0796 (16)	0.0631 (15)	0.0410 (11)	0.0041 (12)	0.0180 (11)	0.0024 (10)
C5	0.0953 (19)	0.0638 (15)	0.0391 (11)	0.0107 (13)	0.0028 (12)	0.0071 (10)
C6	0.0770 (17)	0.0546 (14)	0.0504 (12)	0.0092 (11)	−0.0085 (12)	0.0005 (11)
C7	0.0563 (13)	0.0454 (12)	0.0521 (12)	0.0046 (9)	−0.0022 (10)	−0.0024 (10)
C8	0.0492 (11)	0.0369 (10)	0.0393 (10)	0.0010 (8)	0.0023 (8)	−0.0042 (8)
C9	0.0373 (10)	0.0456 (11)	0.0464 (11)	−0.0008 (8)	0.0089 (8)	0.0018 (9)
C10	0.0406 (10)	0.0393 (10)	0.0367 (9)	−0.0009 (8)	0.0111 (8)	0.0017 (8)
C11	0.0386 (10)	0.0430 (11)	0.0425 (10)	−0.0031 (8)	0.0124 (8)	−0.0058 (8)
C12	0.0353 (10)	0.0426 (11)	0.0446 (10)	−0.0051 (8)	0.0114 (8)	−0.0028 (9)
C13	0.0358 (10)	0.0385 (10)	0.0431 (10)	−0.0035 (7)	0.0091 (8)	−0.0020 (8)
C14	0.0481 (12)	0.0545 (12)	0.0548 (12)	−0.0011 (10)	0.0151 (10)	0.0091 (10)
C15	0.0593 (14)	0.0559 (13)	0.0539 (12)	0.0031 (10)	0.0056 (10)	0.0149 (10)
C16	0.0415 (11)	0.0560 (13)	0.0676 (14)	0.0057 (9)	0.0020 (10)	0.0089 (11)
C17	0.0344 (10)	0.0588 (13)	0.0607 (12)	−0.0002 (9)	0.0108 (9)	0.0075 (10)
C18	0.0341 (9)	0.0387 (10)	0.0439 (10)	−0.0026 (8)	0.0078 (8)	0.0005 (8)
C19	0.0384 (11)	0.0857 (17)	0.0687 (14)	0.0032 (11)	0.0221 (10)	0.0155 (13)
N1	0.0279 (8)	0.0557 (10)	0.0494 (9)	0.0019 (7)	0.0107 (7)	0.0046 (8)
N2	0.0307 (8)	0.0465 (9)	0.0480 (9)	0.0019 (7)	0.0089 (7)	0.0008 (7)
O1	0.0332 (7)	0.0664 (9)	0.0494 (8)	0.0024 (6)	0.0127 (6)	0.0200 (7)
O2	0.0404 (8)	0.0784 (10)	0.0569 (8)	0.0001 (7)	0.0212 (6)	0.0055 (7)
O3	0.0305 (7)	0.0678 (9)	0.0552 (8)	0.0016 (6)	0.0115 (6)	0.0182 (7)

Geometric parameters (Å, º)

C1—C2	1.368 (2)	C12—N2	1.280 (2)
C1—C10	1.427 (2)	C12—C13	1.470 (2)
C1—C11	1.497 (2)	C12—C19	1.495 (2)
C2—C3	1.402 (3)	C13—C14	1.389 (3)
C2—H2	0.9300	C13—C18	1.403 (2)
C3—C4	1.414 (3)	C14—C15	1.370 (3)
C3—C8	1.419 (3)	C14—H14	0.9300
C4—C5	1.356 (3)	C15—C16	1.373 (3)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.400 (3)	C16—C17	1.364 (3)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.351 (3)	C17—C18	1.383 (2)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.411 (3)	C18—O3	1.355 (2)
C7—H7	0.9300	C19—H19A	0.9600
C8—C9	1.403 (3)	C19—H19B	0.9600
C9—C10	1.365 (2)	C19—H19C	0.9600
C9—H9	0.9300	N1—N2	1.363 (2)
C10—O1	1.359 (2)	N1—H1A	0.8600
C11—O2	1.219 (2)	O1—H1	0.8200
C11—N1	1.353 (2)	O3—H3	0.8200
C2—C1—C10	117.57 (17)	N2—C12—C13	115.81 (15)
C2—C1—C11	116.76 (16)	N2—C12—C19	123.33 (17)
C10—C1—C11	125.66 (16)	C13—C12—C19	120.86 (17)
C1—C2—C3	123.36 (17)	C14—C13—C18	117.12 (17)
C1—C2—H2	118.3	C14—C13—C12	121.90 (16)
C3—C2—H2	118.3	C18—C13—C12	120.98 (16)
C2—C3—C4	123.08 (19)	C15—C14—C13	122.24 (18)
C2—C3—C8	118.20 (16)	C15—C14—H14	118.9
C4—C3—C8	118.71 (18)	C13—C14—H14	118.9
C5—C4—C3	121.0 (2)	C14—C15—C16	119.70 (19)
C5—C4—H4	119.5	C14—C15—H15	120.2
C3—C4—H4	119.5	C16—C15—H15	120.2
C4—C5—C6	120.1 (2)	C17—C16—C15	119.72 (19)
C4—C5—H5	120.0	C17—C16—H16	120.1
C6—C5—H5	120.0	C15—C16—H16	120.1
C7—C6—C5	120.8 (2)	C16—C17—C18	121.17 (18)
C7—C6—H6	119.6	C16—C17—H17	119.4
C5—C6—H6	119.6	C18—C17—H17	119.4
C6—C7—C8	121.0 (2)	O3—C18—C17	117.25 (16)
C6—C7—H7	119.5	O3—C18—C13	122.70 (16)
C8—C7—H7	119.5	C17—C18—C13	120.05 (17)
C9—C8—C7	122.84 (18)	C12—C19—H19A	109.5
C9—C8—C3	118.70 (17)	C12—C19—H19B	109.5
C7—C8—C3	118.45 (18)	H19A—C19—H19B	109.5
C10—C9—C8	121.57 (17)	C12—C19—H19C	109.5
C10—C9—H9	119.2	H19A—C19—H19C	109.5
C8—C9—H9	119.2	H19B—C19—H19C	109.5
O1—C10—C9	120.92 (15)	C11—N1—N2	119.25 (15)
O1—C10—C1	118.48 (15)	C11—N1—H1A	120.4
C9—C10—C1	120.60 (16)	N2—N1—H1A	120.4
O2—C11—N1	121.86 (17)	C12—N2—N1	119.99 (15)
O2—C11—C1	122.29 (17)	C10—O1—H1	109.5
N1—C11—C1	115.85 (15)	C18—O3—H3	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.90	2.6026 (18)	137
O1—H1···O3^i	0.82	1.89	2.6931 (17)	166
O3—H3···N2	0.82	1.77	2.4936 (18)	146

Symmetry code: (i) x+1, y, z.