Literature DB >> 22059051

2-[(Naphthalen-1-yl-methyl-idene)amino]-5-methyl-phenol.

Gabriella Orona, Vanessa Molinar, Frank R Fronczek, Ralph Isovitsch.   

Abstract

The title compound, C(18)H(15)NO, is a Schiff base prepared from an acid-catalyzed condensation reaction between 1-naphthaldehyde and 6-amino-m-cresol. Intra-molecular hydrogen bonding occurs via an O-H⋯N inter-action, generating an S(5) ring motif. Neighboring phenol groups participate in inter-molecular hydrogen bonding through an O-H⋯O inter-action, forming chains. The O atom of the phenol group also participates in an intermolecular C-H⋯O interaction with an H atom of one of the naphthalene rings. The C-N=C-C torsion angle between the phenol and naphthalene rings is -179.8 (2)°. Crystal packing involves stacks with the mol-ecules inter-acting through the π-systems of the C=N with both the phenol system and one of the naphthalene rings.

Entities:  

Year:  2011        PMID： 22059051      PMCID： PMC3200862          DOI： 10.1107/S1600536811034556

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related structures, see: De et al. (2008 ▶); Villalpando et al. (2010 ▶); Yildz et al. (2005 ▶). For bond-length data, see Allen et al. (1987 ▶). For background to the synthesis of Schiff bases, see: Borisova et al. (2007 ▶). For background to the use of Schiff bases in solar energy collection, see: Mak et al. (2009 ▶). For background to the inter­molecular inter­actions of π-systems, see: Jennings et al. (2006 ▶); Zhang et al. (2006 ▶). For a description of hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H15NO M = 261.31 Orthorhombic, a = 4.8246 (10) Å b = 9.766 (2) Å c = 28.024 (7) Å V = 1320.4 (5) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 90 K 0.25 × 0.17 × 0.10 mm

Data collection

Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler) diffractometer 14676 measured reflections 1552 independent reflections 1169 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.090 S = 1.05 1552 reflections 185 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.19 e Å−3 Δρmin = −0.17 e Å−3 Data collection: COLLECT (Nonius 2000 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; 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 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811034556/lr2024sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034556/lr2024Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811034556/lr2024Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H15NOF(000) = 552
Mr = 261.31Dx = 1.314 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1569 reflections
a = 4.8246 (10) Åθ = 2.5–26.0°
b = 9.766 (2) ŵ = 0.08 mm−1
c = 28.024 (7) ÅT = 90 K
V = 1320.4 (5) Å3Fragment, orange
Z = 40.25 × 0.17 × 0.10 mm
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler) diffractometer1169 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
graphiteθmax = 26.1°, θmin = 2.9°
ω and φ scansh = −5→5
14676 measured reflectionsk = −11→12
1552 independent reflectionsl = −34→34
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0412P)2 + 0.1692P] where P = (Fo2 + 2Fc2)/3
1552 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −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.
xyzUiso*/Ueq
O10.7221 (4)0.32980 (18)0.49100 (6)0.0319 (5)
H1O0.572 (6)0.287 (3)0.4823 (10)0.048*
N10.4847 (4)0.3060 (2)0.40411 (7)0.0233 (5)
C10.1310 (5)0.1903 (2)0.35845 (9)0.0242 (6)
C20.0777 (5)0.0959 (2)0.39380 (9)0.0268 (6)
H20.18080.09940.42260.032*
C3−0.1273 (6)−0.0059 (2)0.38802 (10)0.0292 (7)
H3−0.1612−0.06940.41300.035*
C4−0.2771 (6)−0.0136 (3)0.34679 (10)0.0293 (7)
H4−0.4124−0.08350.34310.035*
C5−0.3912 (6)0.0766 (3)0.26682 (9)0.0300 (7)
H5−0.52870.00780.26310.036*
C6−0.3497 (6)0.1687 (3)0.23107 (9)0.0308 (6)
H6−0.45870.16440.20290.037*
C7−0.1459 (6)0.2700 (2)0.23600 (9)0.0291 (7)
H7−0.11500.33300.21070.035*
C80.0095 (5)0.2794 (2)0.27681 (9)0.0269 (6)
H80.14350.35020.27970.032*
C9−0.0265 (5)0.1851 (2)0.31488 (9)0.0237 (6)
C10−0.2324 (5)0.0814 (2)0.30962 (9)0.0241 (6)
C110.3451 (6)0.2966 (3)0.36571 (9)0.0270 (6)
H110.37980.36020.34080.032*
C120.6877 (5)0.4091 (2)0.40997 (8)0.0209 (6)
C130.8054 (5)0.4165 (2)0.45550 (9)0.0229 (6)
C141.0077 (5)0.5127 (2)0.46633 (9)0.0250 (6)
H141.08520.51490.49750.030*
C151.0982 (5)0.6057 (2)0.43233 (9)0.0242 (6)
C160.9835 (5)0.5979 (3)0.38650 (9)0.0254 (6)
H161.04290.66040.36260.030*
C170.7852 (5)0.5008 (2)0.37545 (9)0.0256 (6)
H170.71380.49630.34390.031*
C181.3138 (5)0.7117 (2)0.44451 (9)0.0314 (7)
H18A1.27840.74770.47660.047*
H18B1.30510.78670.42130.047*
H18C1.49830.66980.44360.047*
U11U22U33U12U13U23
O10.0329 (11)0.0365 (11)0.0263 (10)−0.0067 (10)−0.0023 (9)0.0079 (9)
N10.0195 (11)0.0259 (11)0.0246 (12)0.0010 (11)−0.0005 (10)−0.0013 (10)
C10.0213 (14)0.0214 (13)0.0300 (14)0.0024 (13)0.0029 (13)−0.0045 (12)
C20.0269 (15)0.0248 (13)0.0288 (15)0.0030 (13)−0.0005 (12)−0.0026 (12)
C30.0310 (16)0.0219 (13)0.0348 (17)0.0017 (14)0.0077 (15)0.0024 (13)
C40.0268 (16)0.0214 (13)0.0397 (17)−0.0012 (13)0.0065 (14)−0.0023 (13)
C50.0240 (15)0.0280 (13)0.0379 (17)−0.0013 (13)0.0028 (13)−0.0108 (13)
C60.0310 (16)0.0328 (14)0.0286 (15)0.0021 (15)0.0005 (14)−0.0073 (13)
C70.0311 (16)0.0298 (14)0.0263 (16)0.0010 (14)0.0040 (13)−0.0025 (12)
C80.0253 (15)0.0243 (13)0.0310 (15)−0.0009 (12)0.0031 (14)−0.0051 (13)
C90.0226 (14)0.0217 (13)0.0269 (15)0.0030 (13)0.0035 (12)−0.0056 (12)
C100.0224 (15)0.0189 (13)0.0308 (16)0.0038 (12)0.0049 (12)−0.0082 (12)
C110.0266 (15)0.0265 (14)0.0279 (15)0.0035 (14)0.0032 (13)−0.0011 (12)
C120.0186 (13)0.0196 (12)0.0245 (14)0.0049 (13)0.0027 (11)−0.0015 (11)
C130.0253 (14)0.0225 (12)0.0210 (13)0.0052 (13)0.0018 (12)0.0020 (12)
C140.0261 (14)0.0266 (13)0.0222 (14)0.0051 (13)−0.0048 (13)−0.0030 (12)
C150.0204 (14)0.0199 (12)0.0323 (15)0.0044 (13)0.0019 (12)−0.0049 (12)
C160.0270 (15)0.0247 (13)0.0245 (14)0.0028 (13)0.0026 (12)0.0029 (13)
C170.0297 (16)0.0267 (13)0.0204 (14)0.0032 (14)−0.0018 (12)−0.0006 (12)
C180.0263 (15)0.0271 (13)0.0409 (17)0.0013 (14)−0.0003 (14)−0.0062 (13)
O1—C131.367 (3)C7—H70.9500
O1—H1O0.87 (3)C8—C91.420 (3)
N1—C111.273 (3)C8—H80.9500
N1—C121.414 (3)C9—C101.427 (3)
C1—C21.377 (3)C11—H110.9500
C1—C91.439 (3)C12—C131.398 (3)
C1—C111.479 (3)C12—C171.400 (3)
C2—C31.412 (3)C13—C141.388 (3)
C2—H20.9500C14—C151.387 (3)
C3—C41.365 (4)C14—H140.9500
C3—H30.9500C15—C161.401 (3)
C4—C101.411 (3)C15—C181.507 (3)
C4—H40.9500C16—C171.382 (4)
C5—C61.361 (3)C16—H160.9500
C5—C101.424 (3)C17—H170.9500
C5—H50.9500C18—H18A0.9800
C6—C71.402 (3)C18—H18B0.9800
C6—H60.9500C18—H18C0.9800
C7—C81.370 (3)
C13—O1—H1O109.9 (18)C4—C10—C9119.8 (2)
C11—N1—C12121.1 (2)C5—C10—C9119.0 (2)
C2—C1—C9119.2 (2)N1—C11—C1122.5 (2)
C2—C1—C11120.1 (2)N1—C11—H11118.8
C9—C1—C11120.7 (2)C1—C11—H11118.8
C1—C2—C3121.3 (2)C13—C12—C17117.5 (2)
C1—C2—H2119.3C13—C12—N1115.1 (2)
C3—C2—H2119.3C17—C12—N1127.4 (2)
C4—C3—C2120.5 (2)O1—C13—C14117.8 (2)
C4—C3—H3119.8O1—C13—C12120.9 (2)
C2—C3—H3119.8C14—C13—C12121.3 (2)
C3—C4—C10120.5 (2)C15—C14—C13120.9 (2)
C3—C4—H4119.7C15—C14—H14119.5
C10—C4—H4119.7C13—C14—H14119.5
C6—C5—C10121.3 (3)C14—C15—C16118.0 (2)
C6—C5—H5119.4C14—C15—C18120.8 (2)
C10—C5—H5119.4C16—C15—C18121.2 (2)
C5—C6—C7119.8 (3)C17—C16—C15121.1 (2)
C5—C6—H6120.1C17—C16—H16119.5
C7—C6—H6120.1C15—C16—H16119.5
C8—C7—C6120.9 (3)C16—C17—C12121.1 (2)
C8—C7—H7119.6C16—C17—H17119.4
C6—C7—H7119.6C12—C17—H17119.4
C7—C8—C9121.1 (2)C15—C18—H18A109.5
C7—C8—H8119.4C15—C18—H18B109.5
C9—C8—H8119.4H18A—C18—H18B109.5
C8—C9—C10117.9 (2)C15—C18—H18C109.5
C8—C9—C1123.4 (2)H18A—C18—H18C109.5
C10—C9—C1118.7 (2)H18B—C18—H18C109.5
C4—C10—C5121.2 (2)
C9—C1—C2—C30.3 (4)C1—C9—C10—C5179.3 (2)
C11—C1—C2—C3179.4 (2)C12—N1—C11—C1−179.8 (2)
C1—C2—C3—C40.4 (4)C2—C1—C11—N1−0.5 (4)
C2—C3—C4—C10−1.0 (4)C9—C1—C11—N1178.6 (2)
C10—C5—C6—C70.5 (4)C11—N1—C12—C13173.8 (2)
C5—C6—C7—C8−1.3 (4)C11—N1—C12—C17−7.6 (4)
C6—C7—C8—C91.5 (4)C17—C12—C13—O1−179.6 (2)
C7—C8—C9—C10−0.9 (3)N1—C12—C13—O1−0.9 (3)
C7—C8—C9—C1180.0 (2)C17—C12—C13—C141.2 (4)
C2—C1—C9—C8178.7 (2)N1—C12—C13—C14179.9 (2)
C11—C1—C9—C8−0.4 (4)O1—C13—C14—C15−178.7 (2)
C2—C1—C9—C10−0.4 (3)C12—C13—C14—C150.5 (4)
C11—C1—C9—C10−179.5 (2)C13—C14—C15—C16−1.2 (3)
C3—C4—C10—C5−178.6 (2)C13—C14—C15—C18178.8 (2)
C3—C4—C10—C90.9 (4)C14—C15—C16—C170.2 (4)
C6—C5—C10—C4179.5 (2)C18—C15—C16—C17−179.8 (2)
C6—C5—C10—C90.0 (4)C15—C16—C17—C121.5 (4)
C8—C9—C10—C4−179.4 (2)C13—C12—C17—C16−2.1 (4)
C1—C9—C10—C4−0.2 (3)N1—C12—C17—C16179.3 (2)
C8—C9—C10—C50.1 (3)
D—H···AD—HH···AD···AD—H···A
O1—H1O···O1i0.87 (3)2.17 (3)2.916 (2)143 (2)
O1—H1O···N10.87 (3)2.24 (3)2.701 (3)113 (2)
C2—H2···O1i0.952.533.382 (3)150
C18—H18C···Cgii0.982.573.504 (3)160
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1O⋯O1i0.87 (3)2.17 (3)2.916 (2)143 (2)
O1—H1O⋯N10.87 (3)2.24 (3)2.701 (3)113 (2)
C2—H2⋯O1i0.952.533.382 (3)150
C18—H18C⋯Cgii0.982.573.504 (3)160

Symmetry codes: (i) ; (ii) .

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