NAPHTHALEN-2-OL

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1 [(Di­methyl­amino)(phen­yl)meth­yl]naphthalen 2 ol

1 [(Di­methyl­amino)(phen­yl)meth­yl]naphthalen 2 ol

Compounds derived from naphthalen-2-ol have been of great interest in organic chemistry (Szatmari & Fulop, 2004; Zhao & Sun, 2005). We report herein the crystal structure of the title compound (Fig. 1). The dihedral angle between the naphthyl ring and phenyl ring is 79.83 (6)°. Strong intramolecular O—H···N hydrogen bond [O1—H1A = 0.82 Å, H1A···N1 = 1.87 Å, O1···N1 = 2.593 (3) Å, O1—H1A···N1 = 147°] together with van der Waals interactions stabilize the molecular conformation.

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1 [(Pyridin 3 yl)(pyrrolidin 1 yl)meth­yl]naphthalen 2 ol

1 [(Pyridin 3 yl)(pyrrolidin 1 yl)meth­yl]naphthalen 2 ol

C6 0.0420 (16) 0.0414 (15) 0.0502 (16) −0.0009 (13) −0.0074 (13) 0.0022 (13) C7 0.055 (2) 0.0502 (18) 0.067 (2) 0.0037 (15) −0.0013 (16) 0.0044 (16) C8 0.057 (2) 0.062 (2) 0.094 (3) 0.0183 (18) −0.012 (2) −0.006 (2) C9 0.051 (2) 0.073 (2) 0.087 (3) 0.0090 (17) 0.0106 (19) −0.001 (2) C10 0.0516 (19) 0.0483 (18) 0.076 (2) 0.0023 (15) 0.0050 (18) 0.0067 (17) C11 0.0413 (16) 0.0467 (18) 0.0490 (17) 0.0039 (13) −0.0009 (14) 0.0079 (13) C12 0.0474 (18) 0.0503 (19) 0.059 (2) 0.0009 (14) 0.0017 (16) 0.0061 (15) C13 0.065 (2) 0.056 (2) 0.058 (2) 0.0037 (17) 0.0039 (18) 0.0202 (16) C14 0.068 (2) 0.070 (2) 0.0501 (19) 0.0148 (18) −0.0006 (18) 0.0165 (17) C15 0.0473 (17) 0.0655 (19) 0.0453 (17) 0.0141 (16) −0.0021 (14) 0.0004 (15) C16 0.061 (2) 0.078 (3) 0.0500 (19) 0.0149 (19) −0.0091 (18) −0.0046 (18) C17 0.062 (2) 0.080 (3) 0.063 (2) 0.001 (2) −0.0129 (18) −0.016 (2) C18 0.054 (2) 0.068 (2) 0.062 (2) −0.0062 (16) −0.0013 (18) −0.0053 (18) C19 0.0503 (18) 0.0544 (18) 0.0529 (18) 0.0018 (14) −0.0016 (15) 0.0019 (15) C20 0.0382 (15) 0.0534 (17) 0.0479 (16) 0.0102 (13) 0.0027 (13) 0.0026 (13) N1 0.0490 (14) 0.0443 (13) 0.0497 (14) 0.0044 (11) 0.0034 (12) 0.0036 (11) N2 0.067 (2) 0.0563 (19) 0.092 (2) 0.0165 (16) −0.0065 (19) 0.0065 (17) O1 0.0666 (15) 0.0538 (13) 0.0643 (14) −0.0110 (12) −0.0020 (13) 0.0119 (11)

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1 [(E) 2 (5 tert Butyl 2 hy­dr­oxy­phen­yl)diazen 1 yl]naphthalen 2 ol

1 [(E) 2 (5 tert Butyl 2 hy­dr­oxy­phen­yl)diazen 1 yl]naphthalen 2 ol

The title compound was obtained through the diazotization of 4-tert-butyl-2-hydroxyaniline followed by a coupling reaction with 2-naphthol, according to the literature procedure used to synthesize other aromatic azo-compounds (Wang et al., 2003). Single crystals of the title compound were obtained by slow evaporation at room temperature of a solution in DMSO.

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Crystal structure of 1 {(E) [(3,4 di­chloro­phen­yl)imino]­meth­yl}naphthalen 2 ol

Crystal structure of 1 {(E) [(3,4 di­chloro­phen­yl)imino]­meth­yl}naphthalen 2 ol

The crystal structures of (E)-1-[(2-chloro-4-nitrophenylimino)methyl]naphthalen-2-ol (Wang et al., 2011), N-(3-chloro- phenyl)-2-hydroxy-1-naphthaldimine (Pavlovic et al., 2002), N-(2-hydroxy-1-naphthylmethylene)-2,5-dichloroaniline (Yildiz et al., 2006), 1-(((4-chlorophenyl)imino)methyl)-2-naphthol (Pierens et al., 2002) and N-(3,5-dichlorophenyl)- naphthaldimine (Elmali et al., 1998) have been published which are related to the title compound (I, Fig. 1).

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Crystal structure of (E) 1 {[(3,5 di­methyl­phen­yl)imino]­meth­yl}naphthalen 2 ol

Crystal structure of (E) 1 {[(3,5 di­methyl­phen­yl)imino]­meth­yl}naphthalen 2 ol

For the diverse applications and biological activities of Schiff bases, see: Schiff (1864); Dutta & Das (1988); Chandra & Sangeetika (2004); Cozzi (2004). For the biological activity and optical properties of Schiff bases derived from 2-hy- droxynapthaldehyde, see: Abdel-Rahman et al. (2013a,b, 2014); Abu-Dief et al. (2013).

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Crystal structure of 1,1′ [imidazolidine 1,3 diylbis(methyl­ene)]bis­­(naphthalen 2 ol)

Crystal structure of 1,1′ [imidazolidine 1,3 diylbis(methyl­ene)]bis­­(naphthalen 2 ol)

monoclinic (C2/c) symmetry. The molecule is located on a crystallographic twofold rotation axis with only half a molecule in the asymmetric unit. The imidazolidine ring adopts a twist conformation, with a twist about the ring C—C bond. The crystal structure shows the anticlinal disposition of the two (2- hydroxynaphthalen-1-yl)methyl substituents of the imidazolidine ring. The structure displays two intramolecular O—H N hydrogen bonds, each forming an S(6) ring motif.

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Crystal structure of 1 [(2,3 di­hydro 1H naphtho­[1,2 e][1,3]oxazin 2 yl)meth­yl]naphthalen 2 ol: a possible candidate for new polynaphthoxazine materials

Crystal structure of 1 [(2,3 di­hydro 1H naphtho­[1,2 e][1,3]oxazin 2 yl)meth­yl]naphthalen 2 ol: a possible candidate for new polynaphthoxazine materials

oxazine ring has a half-chair conformation. The 2-hydroxynaphthalen-1-yl substituent is placed in an axial position. There is an intramolecular O—H N hydrogen bond, forming an S(6) graph-set motif. In the crystal, molecules are connected by a pair of C—H interactions into an inversion dimer, which is reinforced by another pair of weak C—H interactions. The dimers are linked by a – interaction [centroid-centroid distance = 3.6268 (17) A ˚ ], consolidating a column along the a axis. Furthermore, the columns interact with each other by a weak C—H interaction, generating a three-dimensional network.

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Crystal structure of 1 ((1E) {(E) 2 [(2 hy­droxy­naphthalen 1 yl)methyl­­idene]hydrazin 1 yl­­idene}meth­yl)naphthalen 2 ol

Crystal structure of 1 ((1E) {(E) 2 [(2 hy­droxy­naphthalen 1 yl)methyl­­idene]hydrazin 1 yl­­idene}meth­yl)naphthalen 2 ol

The title compound was obtained by the reaction of S-benzyldithiocarbazate and 2-Hydroxy-1-napthaldehyde in boiling ethanol. The unexpected formation of the hydrazone was probably due to the decomposition of S-benzyldithiocarbazate in solution resulting in the formation of hydrazine, which then reacted with 2-hydroxy-1-napthaldehyde to form the corresponding hydrazone. The dithiocarbazates are known to decompose on heating.

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Bis(μ cyclo­hexane 1,4 di­carboxyl­ato)bis­­{aqua­[1 (1H imidazo[4,5 f][1,10]phenanthrolin 2 yl)naphthalen 2 ol]cadmium} monohydrate

Bis(μ cyclo­hexane 1,4 di­carboxyl­ato)bis­­{aqua­[1 (1H imidazo[4,5 f][1,10]phenanthrolin 2 yl)naphthalen 2 ol]cadmium} monohydrate

complex, which lies about an inversion centre, and a half- occupancy solvent water molecule on a general position. Each Cd II cation is six-coordinated by the two N atoms from one 1-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol (L) ligand and three O atoms from two different 1,4-chdc 2 ligands (1,4-H 2 chdc = cyclohexane-1,4-dicarboxylic acid), two

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Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E) 1 [(2,4,6 tri­bromo­phen­yl)diazen­yl]naphthalen 2 ol

Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E) 1 [(2,4,6 tri­bromo­phen­yl)diazen­yl]naphthalen 2 ol

Recently, 1-phenylazo-2-naphthol derivatives have attracted attention because the phenylazo-naphtholate group can provide N,O-bidentate chelation to stabilize transition or main group metal complexes. Azo-metal chelates have also attracted increasing attention due to their interesting elec- tronic and geometrical features in connection with their applications in molecular memory storage, non-linear optical elements and printing systems. Another advantage of

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1 [(Pyrrolidin 1 yl)(p tol­yl)meth­yl]naphthalen 2 ol

1 [(Pyrrolidin 1 yl)(p tol­yl)meth­yl]naphthalen 2 ol

C14 0.0407 (12) 0.0626 (16) 0.0748 (18) −0.0043 (11) 0.0055 (12) −0.0118 (13) C15 0.0343 (12) 0.0621 (16) 0.0671 (16) 0.0008 (10) 0.0062 (11) −0.0113 (12) C16 0.0313 (10) 0.0451 (12) 0.0409 (12) −0.0050 (9) 0.0086 (9) 0.0021 (9) C17 0.0527 (13) 0.0446 (13) 0.0473 (13) 0.0006 (10) 0.0168 (11) 0.0070 (10) C18 0.0560 (14) 0.0626 (16) 0.0433 (13) −0.0062 (12) 0.0198 (11) 0.0010 (11) C19 0.0335 (11) 0.0544 (14) 0.0543 (15) −0.0033 (10) 0.0105 (10) −0.0063 (11) C20 0.0415 (12) 0.0446 (13) 0.0584 (15) 0.0059 (10) 0.0088 (11) 0.0044 (10) C21 0.0411 (11) 0.0499 (14) 0.0440 (13) 0.0009 (10) 0.0085 (10) 0.0067 (10) C22 0.0627 (17) 0.077 (2) 0.0782 (19) 0.0021 (14) 0.0275 (15) −0.0171 (15) N1 0.0309 (9) 0.0458 (10) 0.0463 (11) −0.0024 (7) 0.0093 (8) −0.0028 (8) O1 0.0508 (10) 0.0634 (12) 0.0733 (13) −0.0053 (8) 0.0102 (9) 0.0243 (9)

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(E) 1 [(3 Bromo­phen­yl)imino­meth­yl]naphthalen 2 ol

(E) 1 [(3 Bromo­phen­yl)imino­meth­yl]naphthalen 2 ol

The present X-ray investigation shows that the title compound, (I), prefers the enol-imine tautomeric form rather than the keto-amine tautomeric form (Fig. 1). The C9—O1 and C7—N1 bond lengths verify the enol-imine tautomeric form; these distances agree with the literature [1.310 (8) and 1.319 (6) Å; Ünver et al., 2000], which also shows the enol-imine tautomeric form. The C6—Br1 bond length in (I) is also in a good agreement with the corresponding distance in the literature [1.904 (2) Å; Ünver et al., 2000]. The molecule is non-planar. The dihedral angle between the two Schiff base moieties (C1–C6/N1) and (C7–C13/O1) is 16.27 (12)°. A view of the crystal packing of the title compound is shown in Fig. 2. π–π interactions between the centroids of the Cg1 and Cg2 rings [distance between ring centroids = 4.6002 (19) Å], and the Cg2 and Cg3 rings [distance between ring centroids = 4.805 (2) Å], stack the molecules along the b-axis. Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C8–C13 and C12–C17 rings, respectively.

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A perchlorate salt of 1 [(2 di­methyl­amino­ethyl­imino)meth­yl]naphthalen 2 ol

A perchlorate salt of 1 [(2 di­methyl­amino­ethyl­imino)meth­yl]naphthalen 2 ol

The bond lengths in (I) show normal values (Allen et al., 1987). As expected, the molecule adopts a trans configuration with respect to the C11 N1 double bond. An intramolecular N1—H1 O5 hydrogen bond is observed in the molecular structure (Fig. 1). The cations are linked into chains via N2— H2A O5(x 1, y, z) hydrogen bonds along the a axis. The chains are interlinked into layers parallel to the ac plane by C—H O hydrogen bonds involving the perchlorate O atoms (Fig. 2 and Table 1).

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(E) 1 [(2,4,6 Tri­bromo­phen­yl)diazen­yl]naphthalen 2 ol

(E) 1 [(2,4,6 Tri­bromo­phen­yl)diazen­yl]naphthalen 2 ol

The pH of solution is quite important; it must be mildly acidic or neutral, since no reaction takes place if the pH is too low (Heinrich et al., 2007). We report herein the crystal structure of the title compound (Fig. 1), obtained through the diazotization of 2,4,6-tribromoaniline followed by a coupling reaction with 2-naphthol. In the molecule of the title compound, all bond lengths are in good agreement with those reported for other azo compounds (Deveci et al., 2005; El- Ghamry et al., 2008). The bond lengths and angles are within normal ranges. The naphthalene ring system is oriented at a dihedral angle of 33.80 (16)° with respect to the benzene ring. In the crystal, molecules are packed into columns along the a axis by π–π interactions between adjacent molecules with the closest approach between centroids of aromatic rings

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(E) 1 [(3 Iodo­phen­yl)imino­meth­yl]naphthalen 2 ol

(E) 1 [(3 Iodo­phen­yl)imino­meth­yl]naphthalen 2 ol

with the corresponding distances in the literature [2.092 (4)Â; Manvizhi et al., 2011]. The bond distances for O1-H1O1 and N1-H1O1 are 0.82 and 1.82 Â, respectively, and the N1···H1—O1 angle is 148 Å. These distances and angle agree with the literature[Ünver et al. 2000], The title molecule with the atom-numbering scheme. The displacement ellipsoids are drawn at the 30% probability level. The dashed line indicates the intramolecular hydrogen bond. An ORTEP-3 (Farrugia, 1997) packing diagram of (I), viewed along the b axis. The molecule is non-planar. The angle between the two Schiff base moieties [C1—C6,N1,I1] and [C7—C13,O1,N1] is 20.07 (13) Å. Cg(1), Cg(2) and Cg(3) are the centroids of rings C1—C6, C8—C13 and C12—C17, respectively. However, π···π interactions between the centroids of the Cg(1) and Cg(2) rings (distance between ring centroids = 4.664 (3) Â), and the Cg(2) and Cg(3) rings (distance between ring

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1 {(E) [(2 Fluoro 5 nitro­phen­yl)imino]­meth­yl}naphthalen 2 ol

1 {(E) [(2 Fluoro 5 nitro­phen­yl)imino]­meth­yl}naphthalen 2 ol

As seen in Fig. 1, the title molecule (I) is nearly planar with maximum deviations of 0.197 (1) Å for O3, -0.157 (1) Å for C9 and 0.145 (2) Å for C6. The napthalene ring system (C1–C10) makes a dihedral angle of 5.04 (6) ° with the the benzene ring (C12–C17) of the 1-fluoro-4-nitrobenzene group. The C1–C11–N1–C12, F1–C13–C12–N1, O1–C2–C1– C11, O2–N2–C16—C17 and O3–N2–C16 C15 torsion angles are -179.56 (13), -179.39 (13), 2.4 (2), -8.9 (2) and -9.7 (2) °, respectively. All bond lengths and angles are similar to those of a related structure previously reported (Akkurt et al., 2012).

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1 {(E) [4 Bromo 2 (tri­fluoro­meth­­oxy)phen­yl]imino­meth­yl}naphthalen 2 ol

1 {(E) [4 Bromo 2 (tri­fluoro­meth­­oxy)phen­yl]imino­meth­yl}naphthalen 2 ol

Br1 0.0931 (3) 0.0795 (3) 0.0783 (3) −0.0037 (3) −0.02406 (19) −0.0046 (3) F1 0.157 (3) 0.111 (2) 0.120 (2) 0.0348 (19) 0.034 (2) −0.0057 (19) F2 0.119 (2) 0.0595 (18) 0.230 (4) −0.0058 (17) −0.011 (2) 0.026 (2) F3 0.1036 (19) 0.107 (2) 0.134 (2) 0.0219 (16) −0.0291 (17) 0.0330 (18) N1 0.0728 (19) 0.063 (2) 0.0594 (19) 0.0005 (16) −0.0006 (16) −0.0015 (16) O1 0.103 (2) 0.063 (2) 0.084 (2) 0.0087 (17) −0.0090 (18) −0.0022 (17) O2 0.0727 (16) 0.0599 (18) 0.0845 (19) 0.0017 (15) 0.0006 (14) 0.0078 (14)

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1 [(2 Methyl­piperidin 1 yl)(phen­yl)meth­yl]naphthalen 2 ol

1 [(2 Methyl­piperidin 1 yl)(phen­yl)meth­yl]naphthalen 2 ol

In (I) (Fig. 1), the bond lengths and angles are within the expected ranges corresponding to those observed in the related compounds (Wang & Zhao 2009; Lu et al. 2002). The dihedral angle between the naphthalene ring system and the benzene ring is 75.8 (2)°. The piperidine ring adopts a chair conformation, An intramolecular O—H···N hydrogen bond (Table 1) stabilize the molecular conformation. The crystal packing exhibits no short intermolecular contacts.

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A perchlorate salt of 1 {[2 (2 hy­droxy­ethyl­amino)ethyl­imino]meth­yl}naphthalen 2 ol

A perchlorate salt of 1 {[2 (2 hy­droxy­ethyl­amino)ethyl­imino]meth­yl}naphthalen 2 ol

In compound, (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). As expected, the cation adopts a trans configuration with respect to the C11 N1 bond. In the crystal structure, the ions are linked through weak inter- molecular N—H O, O—H O and C—H O hydrogen bonds, forming columns along the b axis (Fig. 2 and Table 1).

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1 [N (p Hydro­xy­phenyl)­amino­methyl­­idene]­naphthalen 2(1H) one propan 1 ol hemisolvate

1 [N (p Hydro­xy­phenyl)­amino­methyl­­idene]­naphthalen 2(1H) one propan 1 ol hemisolvate

(11) 0.0005 (10) 0.0110 (8) −0.0044 (9) C29 0.0582 (10) 0.0575 (12) 0.0491 (9) −0.0007 (9) 0.0090 (8) −0.0053 (9) C30 0.0618 (11) 0.0630 (12) 0.0447 (8) 0.0020 (10) 0.0088 (8) 0.0033 (9) C31 0.0574 (10) 0.0617 (12) 0.0493 (9) −0.0027 (9) 0.0106 (8) 0.0045 (9) C32 0.0557 (10) 0.0624 (12) 0.0459 (9) −0.0013 (9) 0.0079 (8) 0.0010 (8) C33 0.0740 (12) 0.0828 (15) 0.0444 (9) −0.0090 (11) 0.0089 (9) 0.0074 (9) C34 0.0781 (13) 0.0749 (14) 0.0539 (10) −0.0138 (11) 0.0156 (9) 0.0082 (10) C35 0.113 (2) 0.108 (3) 0.239 (4) 0.0142 (19) 0.087 (2) 0.038 (2) C36 0.174 (3) 0.135 (3) 0.239 (4) 0.026 (3) 0.107 (3) 0.028 (3) C37 0.241 (4) 0.104 (3) 0.282 (5) 0.034 (3) 0.162 (4) 0.030 (3) N1 0.0581 (9) 0.0659 (11) 0.0448 (8) −0.0036 (8) 0.0067 (7) −0.0021 (7) N2 0.0671 (10) 0.0650 (11) 0.0530 (9) −0.0077 (9) 0.0115 (8) −0.0054 (8) O1 0.0691 (8) 0.0891 (10) 0.0511 (6) −0.0193 (7) 0.0098 (6) −0.0038 (6) O2 0.1062 (11) 0.1173 (12) 0.0453 (7) −0.0290 (9) 0.0088 (6) 0.0045 (7) O3 0.0896 (9) 0.0871 (11) 0.0657 (8) −0.0205 (8) 0.0237 (7) −0.0054 (7) O4 0.0675 (7) 0.0861 (10) 0.0483 (6) −0.0126 (7) 0.0031 (6) 0.0042 (6) O5 0.0898 (10) 0.0994 (12) 0.0870 (9) −0.0037 (9) 0.0190 (8) 0.0011 (8)

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