organic compounds
1-[(3-Methylpiperidin-1-yl)(3-nitrophenyl)methyl]naphthalen-2-ol
aSchool of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: zhaohong@seu.edu.cn
The title compound, C23H24N2O3, was synthesized from naphthalen-2-ol, 3-nitrobenzaldehyde and 3-methylpiperidine. The dihedral angles between the naphthalene system and the nitrobenzene and methylpiperidine rings are 78.53 (13) and 64.14 (15)°, respectively. The molecular conformation is stabilized by a strong intramolecular O—H⋯N hydrogen bond.
Related literature
For applications of naphthalen-2-ol derivatives in catalytic ). For related structures, see: Zhao & Sun (2005); Wang & Zhao (2009); Xiao & Zhao (2010);
see: Szatmari & Fulop (2004Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku, 2005); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC.
Supporting information
https://doi.org/10.1107/S1600536810045149/bx2327sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045149/bx2327Isup2.hkl
A dry 50 ml flask was charged with 3-nitrobenzaldehyde (10 mmol), naphthalen-2-ol (10 mmol) and 3-methylpiperidine (10 mmol). The mixture was stirred at 100°C for 12 h and then added ethanol (15 ml), after heated under reflux for 1 h, the precipitate was filtrated out and washed with ethanol for three times to give (I). Colourless crystals suitable for X-ray diffraction were obtained by slow evaporation of a dichloromethane solution.
All H atoms were detected in a difference map, but were placed in calculated positions and refined using a riding motion approxmation, with C—H=0.93–0.98 Å, with Uiso(H)=1.2Ueq(C) and Uiso(Hmethyl)=1.2Ueq(Cmethyl); O—H=0.82 Å, with Uiso(H)=1.5Ueq(O).
Compounds derived from naphthalen-2-ol have been of great interest in organic chemistry due to their application in catalytic
(Szatmari & Fulop, 2004; Zhao & Sun, 2005). As an extension of our work on the structural characterization of naphthol compounds (Wang & Zhao, 2009; Xiao & Zhao, 2010), we report here the structure of (I). In the title compound (Fig. 1) bond lengths and angles have normal values.The dihedral angle between the naphthylen fragment with the nitrobenzene and methyl piperidine rings are 78.53 (13) and 64.14 (15)° respectively. The is stabilized by one strong intramolecular O—H···N hydrogen bonding (Table 1).For applications of naphthalen-2-ol derivatives in catalytic
see: Szatmari & Fulop (2004). For related structures, see: Zhao & Sun (2005); Wang & Zhao (2009); Xiao & Zhao (2010);Data collection: CrystalClear (Rigaku, 2005); cell
CrystalClear (Rigaku, 2005); data reduction: SHELXS97 (Sheldrick, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. The displacement ellipsoids are drawn at the 30% probability level. |
C23H24N2O3 | F(000) = 1600 |
Mr = 376.44 | Dx = 1.256 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 4541 reflections |
a = 11.980 (2) Å | θ = 2.3–27.5° |
b = 10.965 (2) Å | µ = 0.08 mm−1 |
c = 30.30 (3) Å | T = 295 K |
V = 3980 (4) Å3 | Prism, colourless |
Z = 8 | 0.25 × 0.22 × 0.18 mm |
Rigaku SCXmini diffractometer | 3877 independent reflections |
Radiation source: fine-focus sealed tube | 2409 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.110 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 26.0°, θmin = 2.6° |
CCD_Profile_fitting scans | h = −14→14 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −13→13 |
Tmin = 0.982, Tmax = 0.992 | l = −37→37 |
34080 measured reflections |
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)] = 0.083 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.174 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0563P)2 + 1.4193P] where P = (Fo2 + 2Fc2)/3 |
3877 reflections | (Δ/σ)max < 0.001 |
255 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C23H24N2O3 | V = 3980 (4) Å3 |
Mr = 376.44 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 11.980 (2) Å | µ = 0.08 mm−1 |
b = 10.965 (2) Å | T = 295 K |
c = 30.30 (3) Å | 0.25 × 0.22 × 0.18 mm |
Rigaku SCXmini diffractometer | 3877 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 2409 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.992 | Rint = 0.110 |
34080 measured reflections |
R[F2 > 2σ(F2)] = 0.083 | 0 restraints |
wR(F2) = 0.174 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.14 e Å−3 |
3877 reflections | Δρmin = −0.15 e Å−3 |
255 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7000 (2) | 0.9558 (2) | 0.65000 (10) | 0.0433 (7) | |
C2 | 0.6194 (2) | 1.0425 (3) | 0.64171 (11) | 0.0523 (8) | |
C3 | 0.5315 (3) | 1.0634 (3) | 0.67144 (13) | 0.0659 (9) | |
H3 | 0.4769 | 1.1206 | 0.6646 | 0.079* | |
C4 | 0.5255 (3) | 1.0015 (4) | 0.70975 (13) | 0.0707 (10) | |
H4 | 0.4661 | 1.0161 | 0.7288 | 0.085* | |
C5 | 0.6075 (3) | 0.9147 (3) | 0.72156 (11) | 0.0584 (9) | |
C6 | 0.6961 (2) | 0.8920 (3) | 0.69134 (10) | 0.0478 (7) | |
C7 | 0.7785 (3) | 0.8061 (3) | 0.70421 (10) | 0.0552 (8) | |
H7 | 0.8381 | 0.7905 | 0.6854 | 0.066* | |
C8 | 0.7725 (3) | 0.7459 (3) | 0.74356 (11) | 0.0708 (10) | |
H8 | 0.8279 | 0.6904 | 0.7513 | 0.085* | |
C9 | 0.6840 (3) | 0.7671 (4) | 0.77209 (12) | 0.0820 (12) | |
H9 | 0.6796 | 0.7246 | 0.7986 | 0.098* | |
C10 | 0.6041 (3) | 0.8493 (4) | 0.76161 (12) | 0.0774 (11) | |
H10 | 0.5457 | 0.8630 | 0.7812 | 0.093* | |
C11 | 0.7905 (2) | 0.9244 (2) | 0.61686 (9) | 0.0422 (7) | |
H11 | 0.8033 | 0.8363 | 0.6189 | 0.051* | |
C12 | 0.6680 (3) | 0.8576 (3) | 0.55808 (11) | 0.0599 (9) | |
H12A | 0.6106 | 0.8529 | 0.5806 | 0.072* | |
H12B | 0.7044 | 0.7787 | 0.5564 | 0.072* | |
C13 | 0.6143 (3) | 0.8861 (3) | 0.51400 (13) | 0.0728 (11) | |
H13 | 0.5776 | 0.9657 | 0.5166 | 0.087* | |
C14 | 0.7021 (4) | 0.8968 (4) | 0.47882 (13) | 0.0945 (14) | |
H14A | 0.6680 | 0.9242 | 0.4515 | 0.113* | |
H14B | 0.7353 | 0.8175 | 0.4736 | 0.113* | |
C15 | 0.7918 (3) | 0.9860 (4) | 0.49260 (11) | 0.0828 (12) | |
H15A | 0.8513 | 0.9851 | 0.4709 | 0.099* | |
H15B | 0.7605 | 1.0676 | 0.4933 | 0.099* | |
C16 | 0.8395 (3) | 0.9559 (3) | 0.53738 (10) | 0.0633 (9) | |
H16A | 0.8776 | 0.8780 | 0.5361 | 0.076* | |
H16B | 0.8936 | 1.0176 | 0.5457 | 0.076* | |
C17 | 0.5250 (4) | 0.7925 (3) | 0.50331 (16) | 0.1061 (16) | |
H17A | 0.4876 | 0.8153 | 0.4765 | 0.159* | |
H17B | 0.4719 | 0.7892 | 0.5270 | 0.159* | |
H17C | 0.5590 | 0.7139 | 0.4996 | 0.159* | |
C18 | 0.9014 (2) | 0.9868 (3) | 0.62676 (9) | 0.0428 (7) | |
C19 | 1.0000 (2) | 0.9224 (3) | 0.62142 (9) | 0.0472 (7) | |
H19 | 0.9988 | 0.8410 | 0.6128 | 0.057* | |
C20 | 1.0999 (3) | 0.9808 (3) | 0.62900 (10) | 0.0553 (8) | |
C21 | 1.1060 (3) | 1.1004 (4) | 0.64166 (12) | 0.0710 (10) | |
H21 | 1.1746 | 1.1379 | 0.6463 | 0.085* | |
C22 | 1.0079 (3) | 1.1635 (3) | 0.64731 (13) | 0.0748 (10) | |
H22 | 1.0099 | 1.2448 | 0.6560 | 0.090* | |
C23 | 0.9067 (3) | 1.1075 (3) | 0.64020 (11) | 0.0584 (8) | |
H23 | 0.8410 | 1.1512 | 0.6445 | 0.070* | |
N1 | 0.7505 (2) | 0.9505 (2) | 0.57076 (7) | 0.0469 (6) | |
N2 | 1.2039 (3) | 0.9098 (4) | 0.62304 (11) | 0.0788 (9) | |
O1 | 0.61885 (19) | 1.11174 (19) | 0.60442 (8) | 0.0645 (6) | |
H1 | 0.6631 | 1.0833 | 0.5865 | 0.097* | |
O2 | 1.1967 (2) | 0.8052 (3) | 0.61087 (11) | 0.1051 (10) | |
O3 | 1.2920 (2) | 0.9589 (3) | 0.63113 (13) | 0.1305 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0363 (15) | 0.0400 (15) | 0.0536 (18) | −0.0022 (13) | −0.0002 (13) | −0.0087 (13) |
C2 | 0.0470 (18) | 0.0457 (17) | 0.064 (2) | −0.0034 (15) | −0.0002 (15) | −0.0073 (15) |
C3 | 0.047 (2) | 0.066 (2) | 0.085 (3) | 0.0061 (17) | 0.0059 (18) | −0.010 (2) |
C4 | 0.048 (2) | 0.084 (3) | 0.079 (3) | −0.0049 (19) | 0.0190 (18) | −0.019 (2) |
C5 | 0.0454 (19) | 0.068 (2) | 0.062 (2) | −0.0110 (17) | 0.0083 (16) | −0.0132 (17) |
C6 | 0.0440 (17) | 0.0445 (16) | 0.0550 (19) | −0.0103 (14) | −0.0010 (14) | −0.0083 (14) |
C7 | 0.057 (2) | 0.0570 (19) | 0.0515 (19) | −0.0080 (16) | 0.0011 (15) | −0.0019 (15) |
C8 | 0.072 (2) | 0.086 (3) | 0.054 (2) | −0.001 (2) | 0.0013 (18) | 0.0116 (19) |
C9 | 0.080 (3) | 0.109 (3) | 0.057 (2) | −0.012 (3) | 0.004 (2) | 0.020 (2) |
C10 | 0.064 (2) | 0.110 (3) | 0.058 (2) | −0.017 (2) | 0.0178 (19) | −0.006 (2) |
C11 | 0.0437 (17) | 0.0387 (15) | 0.0443 (16) | 0.0001 (13) | −0.0026 (13) | −0.0012 (12) |
C12 | 0.067 (2) | 0.0439 (17) | 0.069 (2) | −0.0014 (16) | −0.0200 (17) | −0.0041 (15) |
C13 | 0.086 (3) | 0.0478 (19) | 0.085 (3) | 0.0037 (19) | −0.040 (2) | −0.0030 (18) |
C14 | 0.134 (4) | 0.089 (3) | 0.060 (3) | 0.004 (3) | −0.028 (3) | −0.002 (2) |
C15 | 0.105 (3) | 0.090 (3) | 0.053 (2) | −0.001 (2) | −0.009 (2) | 0.006 (2) |
C16 | 0.072 (2) | 0.067 (2) | 0.051 (2) | 0.0067 (19) | −0.0002 (17) | −0.0001 (16) |
C17 | 0.115 (4) | 0.070 (3) | 0.134 (4) | −0.009 (2) | −0.071 (3) | −0.004 (2) |
C18 | 0.0425 (17) | 0.0462 (17) | 0.0397 (16) | −0.0016 (14) | −0.0008 (13) | −0.0007 (12) |
C19 | 0.0503 (18) | 0.0472 (17) | 0.0441 (17) | 0.0015 (15) | −0.0022 (14) | 0.0004 (13) |
C20 | 0.0444 (19) | 0.069 (2) | 0.0522 (19) | −0.0005 (17) | −0.0015 (15) | 0.0060 (16) |
C21 | 0.054 (2) | 0.076 (2) | 0.083 (3) | −0.022 (2) | −0.0081 (19) | −0.005 (2) |
C22 | 0.071 (3) | 0.058 (2) | 0.095 (3) | −0.013 (2) | −0.002 (2) | −0.0178 (19) |
C23 | 0.053 (2) | 0.0474 (18) | 0.075 (2) | −0.0015 (16) | 0.0026 (17) | −0.0117 (16) |
N1 | 0.0488 (14) | 0.0447 (13) | 0.0472 (14) | 0.0003 (12) | −0.0068 (12) | −0.0026 (11) |
N2 | 0.0454 (19) | 0.101 (3) | 0.090 (2) | 0.009 (2) | −0.0059 (16) | 0.011 (2) |
O1 | 0.0670 (16) | 0.0489 (13) | 0.0775 (17) | 0.0158 (11) | 0.0021 (12) | 0.0042 (12) |
O2 | 0.0703 (19) | 0.106 (2) | 0.139 (3) | 0.0348 (18) | −0.0131 (17) | −0.027 (2) |
O3 | 0.0440 (17) | 0.134 (3) | 0.214 (4) | −0.0033 (18) | −0.020 (2) | 0.008 (3) |
C1—C2 | 1.379 (4) | C13—H13 | 0.9800 |
C1—C6 | 1.435 (4) | C14—C15 | 1.511 (5) |
C1—C11 | 1.517 (4) | C14—H14A | 0.9700 |
C2—O1 | 1.361 (4) | C14—H14B | 0.9700 |
C2—C3 | 1.404 (4) | C15—C16 | 1.509 (5) |
C3—C4 | 1.347 (5) | C15—H15A | 0.9700 |
C3—H3 | 0.9300 | C15—H15B | 0.9700 |
C4—C5 | 1.413 (5) | C16—N1 | 1.471 (4) |
C4—H4 | 0.9300 | C16—H16A | 0.9700 |
C5—C10 | 1.410 (5) | C16—H16B | 0.9700 |
C5—C6 | 1.424 (4) | C17—H17A | 0.9600 |
C6—C7 | 1.419 (4) | C17—H17B | 0.9600 |
C7—C8 | 1.365 (4) | C17—H17C | 0.9600 |
C7—H7 | 0.9300 | C18—C19 | 1.386 (4) |
C8—C9 | 1.387 (5) | C18—C23 | 1.387 (4) |
C8—H8 | 0.9300 | C19—C20 | 1.376 (4) |
C9—C10 | 1.353 (5) | C19—H19 | 0.9300 |
C9—H9 | 0.9300 | C20—C21 | 1.368 (5) |
C10—H10 | 0.9300 | C20—N2 | 1.481 (4) |
C11—N1 | 1.505 (4) | C21—C22 | 1.375 (5) |
C11—C18 | 1.524 (4) | C21—H21 | 0.9300 |
C11—H11 | 0.9800 | C22—C23 | 1.376 (4) |
C12—N1 | 1.471 (4) | C22—H22 | 0.9300 |
C12—C13 | 1.515 (5) | C23—H23 | 0.9300 |
C12—H12A | 0.9700 | N2—O2 | 1.207 (4) |
C12—H12B | 0.9700 | N2—O3 | 1.210 (4) |
C13—C14 | 1.502 (5) | O1—H1 | 0.8200 |
C13—C17 | 1.518 (5) | ||
C2—C1—C6 | 118.2 (3) | C13—C14—H14A | 109.5 |
C2—C1—C11 | 122.5 (3) | C15—C14—H14A | 109.5 |
C6—C1—C11 | 119.3 (2) | C13—C14—H14B | 109.5 |
O1—C2—C1 | 122.6 (3) | C15—C14—H14B | 109.5 |
O1—C2—C3 | 116.0 (3) | H14A—C14—H14B | 108.1 |
C1—C2—C3 | 121.4 (3) | C16—C15—C14 | 112.1 (3) |
C4—C3—C2 | 120.7 (3) | C16—C15—H15A | 109.2 |
C4—C3—H3 | 119.6 | C14—C15—H15A | 109.2 |
C2—C3—H3 | 119.6 | C16—C15—H15B | 109.2 |
C3—C4—C5 | 121.3 (3) | C14—C15—H15B | 109.2 |
C3—C4—H4 | 119.3 | H15A—C15—H15B | 107.9 |
C5—C4—H4 | 119.3 | N1—C16—C15 | 110.6 (3) |
C10—C5—C4 | 122.7 (3) | N1—C16—H16A | 109.5 |
C10—C5—C6 | 119.0 (3) | C15—C16—H16A | 109.5 |
C4—C5—C6 | 118.3 (3) | N1—C16—H16B | 109.5 |
C7—C6—C5 | 117.3 (3) | C15—C16—H16B | 109.5 |
C7—C6—C1 | 122.8 (3) | H16A—C16—H16B | 108.1 |
C5—C6—C1 | 120.0 (3) | C13—C17—H17A | 109.5 |
C8—C7—C6 | 121.7 (3) | C13—C17—H17B | 109.5 |
C8—C7—H7 | 119.2 | H17A—C17—H17B | 109.5 |
C6—C7—H7 | 119.2 | C13—C17—H17C | 109.5 |
C7—C8—C9 | 120.2 (4) | H17A—C17—H17C | 109.5 |
C7—C8—H8 | 119.9 | H17B—C17—H17C | 109.5 |
C9—C8—H8 | 119.9 | C19—C18—C23 | 118.8 (3) |
C10—C9—C8 | 120.4 (3) | C19—C18—C11 | 119.5 (3) |
C10—C9—H9 | 119.8 | C23—C18—C11 | 121.7 (3) |
C8—C9—H9 | 119.8 | C20—C19—C18 | 119.0 (3) |
C9—C10—C5 | 121.4 (3) | C20—C19—H19 | 120.5 |
C9—C10—H10 | 119.3 | C18—C19—H19 | 120.5 |
C5—C10—H10 | 119.3 | C21—C20—C19 | 122.6 (3) |
N1—C11—C1 | 110.1 (2) | C21—C20—N2 | 119.6 (3) |
N1—C11—C18 | 112.0 (2) | C19—C20—N2 | 117.8 (3) |
C1—C11—C18 | 113.0 (2) | C20—C21—C22 | 118.1 (3) |
N1—C11—H11 | 107.1 | C20—C21—H21 | 120.9 |
C1—C11—H11 | 107.1 | C22—C21—H21 | 120.9 |
C18—C11—H11 | 107.1 | C21—C22—C23 | 120.6 (3) |
N1—C12—C13 | 111.9 (3) | C21—C22—H22 | 119.7 |
N1—C12—H12A | 109.2 | C23—C22—H22 | 119.7 |
C13—C12—H12A | 109.2 | C22—C23—C18 | 120.8 (3) |
N1—C12—H12B | 109.2 | C22—C23—H23 | 119.6 |
C13—C12—H12B | 109.2 | C18—C23—H23 | 119.6 |
H12A—C12—H12B | 107.9 | C12—N1—C16 | 109.6 (2) |
C14—C13—C12 | 110.1 (3) | C12—N1—C11 | 109.0 (2) |
C14—C13—C17 | 113.3 (4) | C16—N1—C11 | 114.5 (2) |
C12—C13—C17 | 110.3 (3) | O2—N2—O3 | 123.2 (4) |
C14—C13—H13 | 107.6 | O2—N2—C20 | 118.5 (3) |
C12—C13—H13 | 107.6 | O3—N2—C20 | 118.3 (4) |
C17—C13—H13 | 107.6 | C2—O1—H1 | 109.5 |
C13—C14—C15 | 110.6 (3) | ||
C6—C1—C2—O1 | 176.9 (3) | C12—C13—C14—C15 | −52.7 (4) |
C11—C1—C2—O1 | −4.2 (4) | C17—C13—C14—C15 | −176.8 (3) |
C6—C1—C2—C3 | −3.8 (4) | C13—C14—C15—C16 | 53.0 (4) |
C11—C1—C2—C3 | 175.1 (3) | C14—C15—C16—N1 | −56.1 (4) |
O1—C2—C3—C4 | −178.7 (3) | N1—C11—C18—C19 | −95.4 (3) |
C1—C2—C3—C4 | 2.0 (5) | C1—C11—C18—C19 | 139.5 (3) |
C2—C3—C4—C5 | 0.7 (5) | N1—C11—C18—C23 | 83.3 (3) |
C3—C4—C5—C10 | 179.3 (3) | C1—C11—C18—C23 | −41.7 (4) |
C3—C4—C5—C6 | −1.4 (5) | C23—C18—C19—C20 | −0.9 (4) |
C10—C5—C6—C7 | −1.8 (4) | C11—C18—C19—C20 | 177.8 (3) |
C4—C5—C6—C7 | 178.9 (3) | C18—C19—C20—C21 | 0.0 (5) |
C10—C5—C6—C1 | 178.8 (3) | C18—C19—C20—N2 | 180.0 (3) |
C4—C5—C6—C1 | −0.5 (4) | C19—C20—C21—C22 | 0.6 (5) |
C2—C1—C6—C7 | −176.4 (3) | N2—C20—C21—C22 | −179.4 (3) |
C11—C1—C6—C7 | 4.7 (4) | C20—C21—C22—C23 | −0.2 (6) |
C2—C1—C6—C5 | 3.0 (4) | C21—C22—C23—C18 | −0.7 (6) |
C11—C1—C6—C5 | −175.9 (2) | C19—C18—C23—C22 | 1.3 (5) |
C5—C6—C7—C8 | 1.1 (4) | C11—C18—C23—C22 | −177.5 (3) |
C1—C6—C7—C8 | −179.5 (3) | C13—C12—N1—C16 | −60.4 (3) |
C6—C7—C8—C9 | 0.4 (5) | C13—C12—N1—C11 | 173.6 (3) |
C7—C8—C9—C10 | −1.3 (6) | C15—C16—N1—C12 | 58.8 (3) |
C8—C9—C10—C5 | 0.6 (6) | C15—C16—N1—C11 | −178.4 (3) |
C4—C5—C10—C9 | −179.8 (4) | C1—C11—N1—C12 | −72.9 (3) |
C6—C5—C10—C9 | 1.0 (5) | C18—C11—N1—C12 | 160.5 (2) |
C2—C1—C11—N1 | −26.7 (3) | C1—C11—N1—C16 | 164.0 (2) |
C6—C1—C11—N1 | 152.2 (2) | C18—C11—N1—C16 | 37.3 (3) |
C2—C1—C11—C18 | 99.5 (3) | C21—C20—N2—O2 | −178.3 (4) |
C6—C1—C11—C18 | −81.7 (3) | C19—C20—N2—O2 | 1.7 (5) |
N1—C12—C13—C14 | 57.6 (4) | C21—C20—N2—O3 | 2.6 (5) |
N1—C12—C13—C17 | −176.7 (3) | C19—C20—N2—O3 | −177.4 (3) |
Experimental details
Crystal data | |
Chemical formula | C23H24N2O3 |
Mr | 376.44 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 295 |
a, b, c (Å) | 11.980 (2), 10.965 (2), 30.30 (3) |
V (Å3) | 3980 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.25 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Rigaku SCXmini |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2005) |
Tmin, Tmax | 0.982, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 34080, 3877, 2409 |
Rint | 0.110 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.083, 0.174, 1.12 |
No. of reflections | 3877 |
No. of parameters | 255 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.15 |
Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008).
Acknowledgements
This work was supported financially by a Southeast University grant for young researchers (4007041027).
References
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Szatmari, I. & Fulop, F. (2004). Curr. Org. Synth. 1, 155–165. Web of Science CrossRef CAS Google Scholar
Wang, W. X. & Zhao, H. (2009). Acta Cryst. E65, o1277. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xiao, J. & Zhao, H. (2010). Acta Cryst. E66, o2938. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhao, B. & Sun, Y.-X. (2005). Acta Cryst. E61, m652–m653. CSD CrossRef IUCr Journals Google Scholar
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Compounds derived from naphthalen-2-ol have been of great interest in organic chemistry due to their application in catalytic asymmetric synthesis (Szatmari & Fulop, 2004; Zhao & Sun, 2005). As an extension of our work on the structural characterization of naphthol compounds (Wang & Zhao, 2009; Xiao & Zhao, 2010), we report here the structure of (I). In the title compound (Fig. 1) bond lengths and angles have normal values.The dihedral angle between the naphthylen fragment with the nitrobenzene and methyl piperidine rings are 78.53 (13) and 64.14 (15)° respectively. The molecular conformation is stabilized by one strong intramolecular O—H···N hydrogen bonding (Table 1).