Crystal structure and conformational analysis of 2-hy­droxy-3-(2-methyl­prop-1-en-1-yl)naphthalene-1,4-dione

Sannyele Alcantara Emiliano; Sheyla Welma Duarte Silva; Mariano Alves Pereira; Valeria Rdos Santos Malta; Tatiane Luciano Balliano

doi:10.1107/S2056989015024755

. 2016 Jan 16;72(Pt 2):188–190. doi: 10.1107/S2056989015024755

Crystal structure and conformational analysis of 2-hydroxy-3-(2-methylprop-1-en-1-yl)naphthalene-1,4-dione

Sannyele Alcantara Emiliano ^a, Sheyla Welma Duarte Silva ^a, Mariano Alves Pereira ^a, Valeria Rdos Santos Malta ^a, Tatiane Luciano Balliano ^a,^*

PMCID: PMC4770963 PMID: 26958384

In the structure of the naphthoquinone derivative 2-hydroxy-3-(2-methylprop-1-en-1-yl)naphthalene-1,4-dione, the molecules form a centrosymmetric cyclic dimer through intermolecular O—H⋯O hydrogen bonds which, together with intermolecular C—H⋯O hydrogen bonds and weak π–π ring interactions, give rise to an overall two-dimensional structure.

Keywords: crystal structure, naphthoquinone derivative, molecular conformation, hydrogen bonding

Abstract

In the structure of the title compound, C₁₄H₁₂O₃, the substituent side chain, in which the H atoms of both methyl groups are disordered over six equivalent sites, lies outside of the plane of the naphthalenedione ring. The ring-to-chain C—C—C—C torsion angles are 50.7 (3), −176.6 (2) and 4.9 (4)°. An intramolecular methyl–hydroxy C—H⋯O hydrogen bond is present. In the crystal, molecules are primarily connected by intermolecular O—H⋯O hydrogen bonds, forming a centrosymmetric cyclic dimer motif [graph set R ₂ ²(10)]. Also present is a weak intermolecular C—H⋯O hydrogen bond linking the dimers and a weak π–π ring interaction [ring centroid separation = 3.7862 (13) Å], giving layers parallel to (10-3).

Chemical context

Naphthoquinone compounds exhibit several biological activities, being utilized for the treatment of parasitic diseases (Salas et al., 2008 ▸) some types of cancer (Tonholo et al., 1998 ▸) and cardiovascular disease (Silva & Torres, 2013 ▸). The compound in this study, 2-hydroxy-3-(2-metilprop-1-enol)naphthalene-1,4-dione, C₁₄H₁₂O₃, is a naphthoquinone derivative and the structure is reported herein.

Structural commentary

The molecular structure of the title compound is shown in Fig. 1 ▸. In this structure the side chain is rotated out of the plane of the naphthalenedione ring, with torsion angles C2—C3—C9—C10, C3—C9—C10—C12 and C3—C9—C10—C22 of 50.7 (3), −176.6 (2) and 4.9 (4)°, respectively. Present also in the molecule is an intramolecular methyl C22⋯O3 [2.959 (3) Å; see Table 1 ▸] and a short O3⋯O1 contact [2.665 (2) Å]. When compared with other analogous structures in the literature, e.g. 2-chloro-3-(4-chlorobenzamido)-1,4-naphthoquinone (Brandy et al., 2009 ▸), it is observed that the title compound has similar conformational features with respect to the side chain, which lies out of the naphthoquinone plane.

Molecular conformation and atom-numbering scheme, with non-H atoms drawn at the 50% probability level. The H atoms of the rotationally disordered methyl groups are shown as six equivalent half-occupancy sites.

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯O1ⁱ	0.97 (3)	1.93 (3)	2.770 (2)	143 (3)
C7—H7⋯O2ⁱⁱ	0.93	2.43	3.339 (3)	164
C22—H22C⋯O3	0.96	2.21	2.959 (3)	134

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Supramolecular features

In the crystal, the molecules are connected by classic intermolecular O3—H⋯O1ⁱ hydrogen bonds (Table 1 ▸), forming a centrosymmetric cyclic dimer [graph set Inline graphic (10)] (Bernstein et al., 1995 ▸) (Fig. 2 ▸ a). Also present in the structure is a weak intermolecular C7—H⋯O2ⁱⁱ hydrogen bond [3.339 (3) Å], linking the dimers and a weak π–π ring interaction between the benzene and quinone ring moieties of the parent ring system [ring centroid separation Cg⋯Cg ⁱⁱⁱ = 3.7862 (13) Å; symmetry code: (iii) x + 1, y, z], giving layers parallel to (10 Inline graphic ) (Figs. 2 ▸ b and 3 ▸).

The centrosymmetric dimers formed from the O3—H⋯O1ⁱ hydrogen bonds, viewed (a) along a and (b) along b. For symmetry code (i), see Table 1 ▸.

The crystal packing in the unit cell, showing intra- and intermolecular interactions as dashed lines.

Database survey

A search of the Cambridge Structural Database (Groom & Allen, 2014 ▸) revealed the presence of 40 structures containing the 2-hydroxynaphthalene-1,4-dione core moiety. There were 787 structures which possess the naphthalene-1,4-dione moiety. There are structures similar to the title compound, whichvary depending on the oxidant used in the synthesis.

Synthesis and crystallization

The compound was obtained through to the lapachol oxidation product as can be seen in the scheme below (Hooker, 1936 ▸). The sample was subjected to an ethyl acetate solution at 301 K for crystallization.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The O3-bound H atom was located in a difference Fourier map and was freely refined. The remaining H atoms were positioned geometrically with aromatic C—H = 0.93 Å and U _iso(H) = 1.2U _eq(C). Rotational disorder was identified in the hydrogen atoms of the methyl carbon atoms C12 and C22 and these were included in the refinement over six equivalent 60° sites with 50% occupation, with C—H = 0.96 Å and U _iso(H) = 1.5U _eq(C).

Table 2. Experimental details.

Crystal data
Chemical formula	C₁₄H₁₂O₃
M _r	228.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	4.3564 (2), 16.4069 (8), 15.8598 (7)
β (°)	94.793 (2)
V (Å³)	1129.62 (9)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.14 × 0.11 × 0.10

Data collection
Diffractometer	Nonius KappaCCD
No. of measured, independent and observed [I > 2σ(I)] reflections	4661, 2585, 1802
R _int	0.041
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F ² > 2σ(F ²)], wR(F ²), S	0.061, 0.191, 1.03
No. of reflections	2585
No. of parameters	158
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.30

Open in a new tab

Computer programs: COLLECT (Enraf–Nonius, 2001 ▸), DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▸), SHELXS97 and SHELXL97 (Sheldrick, 2008 ▸), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ▸), Mercury (Macrae et al., 2008 ▸), publCIF (Westrip, 2010 ▸) and PLATON (Spek, 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015024755/zs2357sup1.cif

e-72-00188-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015024755/zs2357Isup2.hkl

e-72-00188-Isup2.hkl^{(124.4KB, hkl)}

Click here for additional data file.^{(4.5KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015024755/zs2357Isup3.cml

CCDC reference: 1444109

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

UFAL, IQB, LabCriMM, CNPq and FAPEAL are acknowledged for support. We thank Professor Dr Antonio Ventura Pinto (in memorium) for his collaboration in the works of this research group, specifically for the synthesis of the title compound.

supplementary crystallographic information

Crystal data

C₁₄H₁₂O₃	F(000) = 480
M_r = 228.24	D_x = 1.342 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2659 reflections
a = 4.3564 (2) Å	θ = 1.0–27.5°
b = 16.4069 (8) Å	µ = 0.09 mm⁻¹
c = 15.8598 (7) Å	T = 293 K
β = 94.793 (2)°	Block, red
V = 1129.62 (9) Å³	0.14 × 0.11 × 0.10 mm
Z = 4

Open in a new tab

Data collection

Nonius KappaCCD diffractometer	1802 reflections with I > 2σ(I)
Radiation source: Enraf-Nonius FR590	R_int = 0.041
Graphite monochromator	θ_max = 27.5°, θ_min = 2.6°
Detector resolution: 9 pixels mm^-1	h = −5→5
CCD rotation images, thick slices scans	k = −19→21
4661 measured reflections	l = −20→20
2585 independent reflections

Open in a new tab

Refinement

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.191	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0946P)² + 0.4119P] where P = (F_o² + 2F_c²)/3
2585 reflections	(Δ/σ)_max < 0.001
158 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Open in a new tab

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

Open in a new tab

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

	x	y	z	U_iso*/U_eq	Occ. (<1)
O3	0.3690 (4)	0.37038 (10)	0.48362 (10)	0.0407 (4)
O1	0.2205 (4)	0.52143 (9)	0.43377 (9)	0.0404 (4)
O2	−0.3406 (4)	0.27382 (9)	0.26721 (10)	0.0481 (5)
C10	0.0940 (5)	0.19603 (13)	0.47932 (13)	0.0395 (5)
C9	0.0749 (5)	0.23006 (12)	0.40272 (13)	0.0386 (5)
H9	0.1126	0.1961	0.3578	0.046*
H1O3	0.448 (7)	0.424 (2)	0.5005 (19)	0.073 (9)*
C4A	−0.3114 (5)	0.41650 (12)	0.28476 (13)	0.0349 (5)
C8A	−0.1689 (5)	0.48205 (13)	0.32860 (13)	0.0348 (5)
C2	0.1441 (5)	0.38047 (12)	0.42115 (13)	0.0351 (5)
C1	0.0733 (5)	0.46622 (12)	0.39675 (13)	0.0350 (5)
C5	−0.5333 (5)	0.43122 (14)	0.21845 (13)	0.0400 (5)
H5	−0.6268	0.3879	0.1885	0.048*
C3	0.0007 (5)	0.31557 (12)	0.38155 (12)	0.0358 (5)
C4	−0.2235 (5)	0.33077 (13)	0.30859 (13)	0.0369 (5)
C6	−0.6151 (5)	0.51093 (14)	0.19709 (14)	0.0426 (5)
H6	−0.7628	0.5207	0.1524	0.051*
C8	−0.2532 (5)	0.56203 (13)	0.30691 (14)	0.0386 (5)
H8	−0.1584	0.6056	0.3362	0.046*
C7	−0.4789 (5)	0.57607 (13)	0.24159 (14)	0.0413 (5)
H7	−0.5389	0.6291	0.2277	0.05*
C12	0.1899 (6)	0.10858 (13)	0.49043 (15)	0.0475 (6)
H12A	0.1919	0.0939	0.5491	0.071*	0.5
H12B	0.3923	0.1015	0.4718	0.071*	0.5
H12C	0.0468	0.0744	0.4575	0.071*	0.5
H12D	0.2288	0.086	0.4365	0.071*	0.5
H12E	0.0283	0.0784	0.5138	0.071*	0.5
H12F	0.3738	0.1055	0.5281	0.071*	0.5
C22	0.0189 (6)	0.23815 (14)	0.55869 (14)	0.0452 (6)
H22A	0.0507	0.2013	0.6056	0.068*	0.5
H22B	−0.1923	0.2554	0.553	0.068*	0.5
H22C	0.1503	0.2848	0.5684	0.068*	0.5
H22D	−0.0449	0.2931	0.5457	0.068*	0.5
H22E	0.1981	0.2389	0.5983	0.068*	0.5
H22F	−0.1445	0.2095	0.583	0.068*	0.5

Open in a new tab

Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0435 (9)	0.0323 (8)	0.0450 (9)	−0.0013 (6)	−0.0051 (6)	−0.0002 (7)
O1	0.0456 (9)	0.0318 (8)	0.0431 (8)	−0.0041 (6)	−0.0005 (6)	−0.0022 (6)
O2	0.0651 (11)	0.0308 (8)	0.0460 (9)	−0.0033 (7)	−0.0096 (7)	−0.0026 (7)
C10	0.0438 (12)	0.0302 (10)	0.0439 (12)	−0.0025 (8)	−0.0013 (9)	−0.0004 (9)
C9	0.0462 (12)	0.0282 (10)	0.0409 (11)	0.0009 (9)	0.0011 (9)	−0.0027 (9)
C4A	0.0422 (11)	0.0292 (10)	0.0340 (10)	−0.0011 (8)	0.0061 (8)	0.0012 (8)
C8A	0.0398 (11)	0.0305 (11)	0.0346 (10)	−0.0016 (8)	0.0057 (8)	−0.0001 (8)
C2	0.0384 (11)	0.0314 (11)	0.0355 (10)	0.0003 (8)	0.0035 (8)	0.0009 (8)
C1	0.0398 (11)	0.0288 (10)	0.0367 (10)	−0.0019 (8)	0.0055 (8)	−0.0034 (8)
C5	0.0486 (13)	0.0343 (11)	0.0368 (11)	−0.0025 (9)	0.0015 (9)	−0.0004 (9)
C3	0.0431 (11)	0.0292 (10)	0.0355 (10)	−0.0006 (8)	0.0064 (8)	−0.0006 (8)
C4	0.0453 (12)	0.0299 (10)	0.0357 (11)	−0.0025 (9)	0.0040 (9)	−0.0011 (8)
C6	0.0500 (13)	0.0383 (12)	0.0391 (11)	0.0013 (9)	0.0003 (9)	0.0039 (9)
C8	0.0460 (12)	0.0293 (10)	0.0410 (11)	−0.0005 (8)	0.0062 (9)	−0.0002 (8)
C7	0.0493 (12)	0.0312 (11)	0.0436 (11)	0.0027 (9)	0.0060 (9)	0.0055 (9)
C12	0.0651 (15)	0.0315 (11)	0.0447 (12)	0.0020 (10)	−0.0024 (10)	0.0011 (9)
C22	0.0587 (14)	0.0346 (11)	0.0420 (12)	0.0006 (10)	0.0033 (10)	0.0011 (9)

Open in a new tab

Geometric parameters (Å, º)

O3—C2	1.344 (3)	C3—C4	1.472 (3)
O3—H1O3	0.97 (4)	C6—C7	1.387 (3)
O1—C1	1.230 (2)	C6—H6	0.93
O2—C4	1.228 (2)	C8—C7	1.387 (3)
C10—C9	1.333 (3)	C8—H8	0.93
C10—C22	1.496 (3)	C7—H7	0.93
C10—C12	1.501 (3)	C12—H12A	0.96
C9—C3	1.472 (3)	C12—H12B	0.96
C9—H9	0.93	C12—H12C	0.96
C4A—C5	1.389 (3)	C12—H12D	0.96
C4A—C8A	1.398 (3)	C12—H12E	0.96
C4A—C4	1.498 (3)	C12—H12F	0.96
C8A—C8	1.398 (3)	C22—H22A	0.96
C8A—C1	1.469 (3)	C22—H22B	0.96
C2—C3	1.361 (3)	C22—H22C	0.96
C2—C1	1.485 (3)	C22—H22D	0.96
C5—C6	1.390 (3)	C22—H22E	0.96
C5—H5	0.93	C22—H22F	0.96

C2—O3—H1O3	108.3 (18)	C10—C12—H12C	109.5
C9—C10—C22	124.9 (2)	H12A—C12—H12C	109.5
C9—C10—C12	120.2 (2)	H12B—C12—H12C	109.5
C22—C10—C12	114.91 (19)	C10—C12—H12D	109.5
C10—C9—C3	127.1 (2)	H12A—C12—H12D	141.1
C10—C9—H9	116.5	H12B—C12—H12D	56.3
C3—C9—H9	116.5	H12C—C12—H12D	56.3
C5—C4A—C8A	119.67 (19)	C10—C12—H12E	109.5
C5—C4A—C4	120.09 (19)	H12A—C12—H12E	56.3
C8A—C4A—C4	120.23 (18)	H12B—C12—H12E	141.1
C4A—C8A—C8	120.21 (19)	H12C—C12—H12E	56.3
C4A—C8A—C1	119.46 (19)	H12D—C12—H12E	109.5
C8—C8A—C1	120.32 (19)	C10—C12—H12F	109.5
O3—C2—C3	121.45 (19)	H12A—C12—H12F	56.3
O3—C2—C1	115.56 (18)	H12B—C12—H12F	56.3
C3—C2—C1	122.95 (19)	H12C—C12—H12F	141.1
O1—C1—C8A	122.31 (19)	H12D—C12—H12F	109.5
O1—C1—C2	119.00 (18)	H12E—C12—H12F	109.5
C8A—C1—C2	118.68 (18)	C10—C22—H22A	109.5
C4A—C5—C6	119.8 (2)	C10—C22—H22B	109.5
C4A—C5—H5	120.1	H22A—C22—H22B	109.5
C6—C5—H5	120.1	C10—C22—H22C	109.5
C2—C3—C4	118.61 (19)	H22A—C22—H22C	109.5
C2—C3—C9	123.83 (19)	H22B—C22—H22C	109.5
C4—C3—C9	117.35 (18)	C10—C22—H22D	109.5
O2—C4—C3	120.66 (19)	H22A—C22—H22D	141.1
O2—C4—C4A	119.58 (18)	H22B—C22—H22D	56.3
C3—C4—C4A	119.76 (18)	H22C—C22—H22D	56.3
C7—C6—C5	120.7 (2)	C10—C22—H22E	109.5
C7—C6—H6	119.6	H22A—C22—H22E	56.3
C5—C6—H6	119.6	H22B—C22—H22E	141.1
C7—C8—C8A	119.7 (2)	H22C—C22—H22E	56.3
C7—C8—H8	120.2	H22D—C22—H22E	109.5
C8A—C8—H8	120.2	C10—C22—H22F	109.5
C6—C7—C8	119.9 (2)	H22A—C22—H22F	56.3
C6—C7—H7	120	H22B—C22—H22F	56.3
C8—C7—H7	120	H22C—C22—H22F	141.1
C10—C12—H12A	109.5	H22D—C22—H22F	109.5
C10—C12—H12B	109.5	H22E—C22—H22F	109.5
H12A—C12—H12B	109.5

O1—C1—C2—O3	0.2 (3)	O2—C4—C4A—C5	2.6 (3)
O1—C1—C2—C3	−177.5 (2)	O2—C4—C4A—C8A	−176.8 (2)
C8A—C1—C2—O3	179.69 (19)	C3—C4—C4A—C5	−177.0 (2)
C8A—C1—C2—C3	2.0 (3)	C3—C4—C4A—C8A	3.5 (3)
O1—C1—C8A—C4A	175.2 (2)	C4—C4A—C5—C6	179.6 (2)
O1—C1—C8A—C8	−3.9 (3)	C8A—C4A—C5—C6	−1.0 (3)
C2—C1—C8A—C4A	−4.3 (3)	C4—C4A—C8A—C1	1.6 (3)
C2—C1—C8A—C8	176.6 (2)	C4—C4A—C8A—C8	−179.4 (2)
O3—C2—C3—C4	−174.50 (19)	C5—C4A—C8A—C1	−177.9 (2)
O3—C2—C3—C9	0.2 (3)	C5—C4A—C8A—C8	1.2 (3)
C1—C2—C3—C4	3.1 (3)	C4A—C5—C6—C7	−0.4 (3)
C1—C2—C3—C9	177.8 (2)	C5—C6—C7—C8	1.5 (3)
C2—C3—C4—O2	174.5 (2)	C6—C7—C8—C8A	−1.3 (3)
C2—C3—C4—C4A	−5.9 (3)	C7—C8—C8A—C1	179.0 (2)
C9—C3—C4—O2	−0.5 (3)	C7—C8—C8A—C4A	−0.1 (3)
C9—C3—C4—C4A	179.15 (19)	C3—C9—C10—C12	−176.6 (2)
C2—C3—C9—C10	50.7 (3)	C3—C9—C10—C22	4.9 (4)
C4—C3—C9—C10	−134.6 (2)

Open in a new tab

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O1ⁱ	0.97 (3)	1.93 (3)	2.770 (2)	143 (3)
C7—H7···O2ⁱⁱ	0.93	2.43	3.339 (3)	164
C22—H22C···O3	0.96	2.21	2.959 (3)	134

Open in a new tab

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x−1, y+1/2, −z+1/2.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.
Brandy, Y., Butcher, R. J., Adesiyun, T. A., Berhe, S. & Bakare, O. (2009). Acta Cryst. E65, o64. [DOI] [PMC free article] [PubMed]
Enraf–Nonius (2001). Kappa CCD Operation Manual. Enraf–Nonius, Delft, The Netherlands.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662–671. [DOI] [PubMed]
Hooker, S. C. (1936). J. Am. Chem. Soc. 58, 1168–1173.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, Editors C. W. Carter & R. M. Sweet, pp. 307–326. New York: Academic Press.
Salas, C., Tapia, R. A., Ciudad, K., Armstrong, V., Orellana, M., Kemmerling, U., Ferreira, J., Maya, J. D. & Morello, A. (2008). Bioorg. Med. Chem. 16, 668–674. [DOI] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Silva, A. K. Soares e, de Oliveira Cipriano Torres, D., Santos Rocha, S. W., dos Santos Gomes, F. O., dos Santos Silva, B., Donato, M. A. M., Raposo, C., Santos, A. C. O., de Lima, M. do C. A., Galdino, S. L., da Rocha Pitta, I., de Souza, J. R. B. & Peixoto, C. A. (2013). Cardiovascular Pathol. 22, 81–90. [DOI] [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
Tonholo, J. L. R., Freitas, L. R., de Abreu, F. C., Azevedo, D. C., Zani, C. L., de Oliveira, A. B. & Goulart, M. O. F. (1998). J. Braz. Chem. Soc. 9, 163–169.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015024755/zs2357sup1.cif

e-72-00188-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015024755/zs2357Isup2.hkl

e-72-00188-Isup2.hkl^{(124.4KB, hkl)}

Click here for additional data file.^{(4.5KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015024755/zs2357Isup3.cml

CCDC reference: 1444109

Additional supporting information: crystallographic information; 3D view; checkCIF report

[bb1] Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.

[bb2] Brandy, Y., Butcher, R. J., Adesiyun, T. A., Berhe, S. & Bakare, O. (2009). Acta Cryst. E65, o64. [DOI] [PMC free article] [PubMed]

[bb3] Enraf–Nonius (2001). Kappa CCD Operation Manual. Enraf–Nonius, Delft, The Netherlands.

[bb4] Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.

[bb5] Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662–671. [DOI] [PubMed]

[bb14] Hooker, S. C. (1936). J. Am. Chem. Soc. 58, 1168–1173.

[bb6] Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.

[bb7] Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, Editors C. W. Carter & R. M. Sweet, pp. 307–326. New York: Academic Press.

[bb8] Salas, C., Tapia, R. A., Ciudad, K., Armstrong, V., Orellana, M., Kemmerling, U., Ferreira, J., Maya, J. D. & Morello, A. (2008). Bioorg. Med. Chem. 16, 668–674. [DOI] [PubMed]

[bb9] Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

[bb10] Silva, A. K. Soares e, de Oliveira Cipriano Torres, D., Santos Rocha, S. W., dos Santos Gomes, F. O., dos Santos Silva, B., Donato, M. A. M., Raposo, C., Santos, A. C. O., de Lima, M. do C. A., Galdino, S. L., da Rocha Pitta, I., de Souza, J. R. B. & Peixoto, C. A. (2013). Cardiovascular Pathol. 22, 81–90. [DOI] [PubMed]

[bb11] Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]

[bb12] Tonholo, J. L. R., Freitas, L. R., de Abreu, F. C., Azevedo, D. C., Zani, C. L., de Oliveira, A. B. & Goulart, M. O. F. (1998). J. Braz. Chem. Soc. 9, 163–169.

[bb13] Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.

PERMALINK

Crystal structure and conformational analysis of 2-hydroxy-3-(2-methylprop-1-en-1-yl)naphthalene-1,4-dione

Sannyele Alcantara Emiliano

Sheyla Welma Duarte Silva

Mariano Alves Pereira

Valeria Rdos Santos Malta

Tatiane Luciano Balliano

Abstract

Chemical context

Structural commentary