Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036719/hk2300sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036719/hk2300Isup2.hkl |
CCDC reference: 657883
The title compound was synthesized by the reaction of 1-naphthalene-acetic acid (1.86 g, 10 mmol) with excessive piperidine (7.1 g, 100 mmol), they were put in a flask, equipped with a magnetic stirrer bar, and the reaction mixture was subjected to microwave irradiation for 10 min under 400 W, then piperidine was refluxed. The reaction flask was allowed to cool to room temperature and the colorless crystals were obtained. They were recrystallized from methanol (yield; 80%, m.p. 417–419 K).
H atoms were positioned geometrically with O—H = 0.82 Å (for OH), N—H = 0.90 Å (for NH), C—H = 0.93 and 0.97 Å for aromatic and methylene atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N,O).
Numerous highly efficient nonlinear optical (NLO) crystals for visible and ultraviolet (UV) regions have been synthesized and studied. They attract considerable attention due to their extreme importance for both laser spectroscopy and laser processing (Prasad & Williams, 1991; Pal et al., 2003). In recent years, many new non-linear optical second harmonic generation (SHG) materials of organic adduct were reported, which have main merits. The main advantage of organic adduct materials compared with inorganic materials for such second-harmonic generation devices are the large macroscopic second-order nonlinear optical susceptibilities, ultrafast optical response time and high optical damage thresholds (Anwar et al., 2000; Muthuraman et al., 2001; Kotler et al., 1992; Wang et al., 2006). At present, adduct assembly is a hot point in designing solid state structures with outstanding conductance, electronic, nonlinear optical or magnetic properties (Brasselet et al., 1999; Rodrigues et al., 2001; Goswami et al., 1999). We report herein the synthesis and structure of a new organic adduct of 1-naphthalene-acetic acid and piperidine.
The asymmetric unit of the title compound, (I), contains two naphthalene-acetic acid and one piperidine moieties (Fig. 1), in which they are held together by intramolecular O—H···O and O—H···N hydrogen bonds (Table 1). The bond lengths and angles are generally within normal ranges (Allen et al., 1987). The two oxygen atoms of each carboxyl groups are conjugated [O1—C12 =1.237 (3) Å, O2—C12 = 1.268 (4) Å and O3—C24 = 1.196 (3) Å, O4—C24 1.322 (4) Å].
Rings A (C1—C10) and B (C13—C22) are, of course, planar and the dihedral angle between them is A/B = 14.20 (2)°. Ring C (N1/C25—C29) is not planar, having total puckering amplitude, QT, of 0.568 (3) Å, and chair conformation [φ = 1.36 (3)° and θ = 1.39 (3)°] (Cremer & Pople, 1975).
In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into dimers (Fig. 2), in which they seem to be effective in the stabilization of the structure.
For general background, see: Prasad & Williams (1991); Pal et al. (2003); Anwar et al. (2000); Muthuraman et al. (2001); Kotler et al. (1992); Wang et al. (2006); Brasselet et al. (1999); Rodrigues et al. (2001); Goswami et al. (1999); Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).
Data collection: XSCANS (Bruker, 1997a); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997b); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
2C12H10O2·C5H11N | F(000) = 976 |
Mr = 457.55 | Dx = 1.241 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 43 reflections |
a = 9.7415 (16) Å | θ = 3.1–13.2° |
b = 19.174 (3) Å | µ = 0.08 mm−1 |
c = 13.6232 (19) Å | T = 295 K |
β = 105.757 (11)° | Plate, colorless |
V = 2449.0 (7) Å3 | 0.4 × 0.3 × 0.2 mm |
Z = 4 |
Bruker P4 diffractometer | Rint = 0.034 |
Radiation source: fine-focus sealed tube | θmax = 25.5°, θmin = 1.9° |
Graphite monochromator | h = −1→11 |
ω scans | k = −1→23 |
5745 measured reflections | l = −16→16 |
4550 independent reflections | 3 standard reflections every 97 reflections |
2552 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.001P)2 + 2P] where P = (Fo2 + 2Fc2)/3 |
4550 reflections | (Δ/σ)max < 0.001 |
309 parameters | Δρmax = 0.56 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
2C12H10O2·C5H11N | V = 2449.0 (7) Å3 |
Mr = 457.55 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.7415 (16) Å | µ = 0.08 mm−1 |
b = 19.174 (3) Å | T = 295 K |
c = 13.6232 (19) Å | 0.4 × 0.3 × 0.2 mm |
β = 105.757 (11)° |
Bruker P4 diffractometer | Rint = 0.034 |
5745 measured reflections | 3 standard reflections every 97 reflections |
4550 independent reflections | intensity decay: none |
2552 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.56 e Å−3 |
4550 reflections | Δρmin = −0.27 e Å−3 |
309 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 | ||
O1 | 0.8603 (2) | 0.55184 (12) | 0.57310 (17) | 0.0701 (6) | |
O2 | 0.6931 (2) | 0.52314 (13) | 0.43362 (19) | 0.0784 (7) | |
H2B | 0.7446 | 0.4890 | 0.4362 | 0.094* | |
O3 | 0.4475 (2) | 0.44149 (12) | 0.23853 (17) | 0.0738 (6) | |
O4 | 0.4474 (2) | 0.54627 (13) | 0.30738 (19) | 0.0825 (7) | |
H4B | 0.5274 | 0.5344 | 0.3405 | 0.099* | |
N1 | 0.8800 (3) | 0.41263 (14) | 0.4533 (2) | 0.0651 (7) | |
H1A | 0.9587 | 0.4285 | 0.4381 | 0.078* | |
C1 | 0.7313 (3) | 0.68434 (17) | 0.5729 (3) | 0.0648 (8) | |
C2 | 0.7634 (5) | 0.7012 (2) | 0.6751 (3) | 0.1009 (15) | |
H2A | 0.7263 | 0.6742 | 0.7185 | 0.121* | |
C3 | 0.8531 (6) | 0.7598 (3) | 0.7158 (3) | 0.123 (2) | |
H3A | 0.8731 | 0.7714 | 0.7845 | 0.148* | |
C4 | 0.9082 (6) | 0.7981 (3) | 0.6505 (5) | 0.123 (2) | |
H4A | 0.9682 | 0.8354 | 0.6763 | 0.148* | |
C5 | 0.9406 (5) | 0.8249 (2) | 0.4817 (5) | 0.1051 (15) | |
H5A | 1.0026 | 0.8618 | 0.5057 | 0.126* | |
C6 | 0.9017 (5) | 0.8058 (3) | 0.3821 (5) | 0.1069 (15) | |
H6A | 0.9412 | 0.8306 | 0.3378 | 0.128* | |
C7 | 0.8084 (5) | 0.7527 (2) | 0.3411 (4) | 0.1053 (15) | |
H7A | 0.7826 | 0.7441 | 0.2712 | 0.126* | |
C8 | 0.7559 (4) | 0.7137 (2) | 0.4036 (3) | 0.0854 (12) | |
H8A | 0.6958 | 0.6767 | 0.3768 | 0.102* | |
C9 | 0.7899 (3) | 0.72764 (17) | 0.5117 (3) | 0.0631 (8) | |
C10 | 0.8784 (4) | 0.7834 (2) | 0.5487 (4) | 0.0867 (12) | |
C11 | 0.6487 (3) | 0.62008 (17) | 0.5313 (3) | 0.0742 (10) | |
H11A | 0.5782 | 0.6317 | 0.4682 | 0.089* | |
H11B | 0.5982 | 0.6040 | 0.5794 | 0.089* | |
C12 | 0.7427 (3) | 0.56126 (17) | 0.5112 (3) | 0.0601 (8) | |
C13 | 0.1607 (3) | 0.46038 (16) | 0.1131 (2) | 0.0583 (8) | |
C14 | 0.0605 (3) | 0.41947 (19) | 0.1382 (3) | 0.0704 (9) | |
H14A | 0.0440 | 0.4250 | 0.2019 | 0.084* | |
C15 | −0.0180 (4) | 0.36970 (19) | 0.0714 (3) | 0.0799 (11) | |
H15A | −0.0850 | 0.3427 | 0.0913 | 0.096* | |
C16 | 0.0026 (4) | 0.36042 (18) | −0.0217 (3) | 0.0747 (10) | |
H16A | −0.0499 | 0.3269 | −0.0655 | 0.090* | |
C17 | 0.1252 (4) | 0.3946 (2) | −0.1509 (3) | 0.0835 (11) | |
H17A | 0.0730 | 0.3615 | −0.1957 | 0.100* | |
C18 | 0.2196 (5) | 0.4348 (3) | −0.1812 (3) | 0.0993 (14) | |
H18A | 0.2317 | 0.4295 | −0.2462 | 0.119* | |
C19 | 0.2995 (4) | 0.4847 (2) | −0.1145 (3) | 0.0895 (12) | |
H19A | 0.3644 | 0.5125 | −0.1356 | 0.107* | |
C20 | 0.2828 (4) | 0.49275 (19) | −0.0192 (3) | 0.0715 (9) | |
H20A | 0.3372 | 0.5258 | 0.0245 | 0.086* | |
C21 | 0.1844 (3) | 0.45178 (16) | 0.0143 (2) | 0.0556 (7) | |
C22 | 0.1035 (3) | 0.40139 (17) | −0.0530 (3) | 0.0636 (8) | |
C23 | 0.2388 (3) | 0.51424 (18) | 0.1867 (2) | 0.0663 (9) | |
H23A | 0.1846 | 0.5238 | 0.2353 | 0.080* | |
H23B | 0.2422 | 0.5570 | 0.1494 | 0.080* | |
C24 | 0.3882 (3) | 0.49526 (17) | 0.2449 (2) | 0.0568 (7) | |
C25 | 0.9207 (4) | 0.38701 (19) | 0.5601 (3) | 0.0777 (10) | |
H25A | 0.9607 | 0.4251 | 0.6059 | 0.093* | |
H25B | 0.9930 | 0.3511 | 0.5679 | 0.093* | |
C26 | 0.7930 (4) | 0.3579 (2) | 0.5876 (3) | 0.0845 (11) | |
H26A | 0.7247 | 0.3949 | 0.5860 | 0.101* | |
H26B | 0.8222 | 0.3393 | 0.6564 | 0.101* | |
C27 | 0.7229 (4) | 0.3007 (2) | 0.5146 (3) | 0.0856 (11) | |
H27A | 0.7870 | 0.2612 | 0.5220 | 0.103* | |
H27B | 0.6367 | 0.2854 | 0.5308 | 0.103* | |
C28 | 0.6867 (4) | 0.3268 (2) | 0.4067 (3) | 0.0817 (11) | |
H28A | 0.6139 | 0.3626 | 0.3976 | 0.098* | |
H28B | 0.6478 | 0.2887 | 0.3606 | 0.098* | |
C29 | 0.8154 (4) | 0.35637 (19) | 0.3797 (3) | 0.0786 (10) | |
H29A | 0.8849 | 0.3197 | 0.3821 | 0.094* | |
H29B | 0.7872 | 0.3751 | 0.3110 | 0.094* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0458 (12) | 0.0723 (15) | 0.0858 (16) | 0.0051 (11) | 0.0072 (11) | −0.0115 (12) |
O2 | 0.0636 (15) | 0.0706 (16) | 0.0902 (17) | 0.0176 (12) | 0.0026 (13) | −0.0111 (14) |
O3 | 0.0680 (14) | 0.0683 (15) | 0.0795 (16) | 0.0157 (12) | 0.0107 (12) | −0.0041 (12) |
O4 | 0.0659 (15) | 0.0759 (16) | 0.0880 (17) | 0.0128 (13) | −0.0095 (13) | −0.0141 (14) |
N1 | 0.0507 (15) | 0.0678 (17) | 0.0759 (18) | −0.0024 (13) | 0.0154 (13) | −0.0070 (15) |
C1 | 0.063 (2) | 0.061 (2) | 0.070 (2) | 0.0162 (16) | 0.0173 (17) | 0.0018 (17) |
C2 | 0.138 (4) | 0.101 (3) | 0.067 (3) | 0.054 (3) | 0.033 (3) | 0.011 (2) |
C3 | 0.161 (5) | 0.129 (5) | 0.054 (3) | 0.063 (4) | −0.014 (3) | −0.032 (3) |
C4 | 0.122 (4) | 0.094 (4) | 0.122 (4) | 0.048 (3) | −0.022 (4) | −0.032 (3) |
C5 | 0.088 (3) | 0.062 (3) | 0.164 (5) | 0.018 (2) | 0.032 (3) | 0.019 (3) |
C6 | 0.101 (4) | 0.085 (3) | 0.141 (5) | 0.008 (3) | 0.044 (3) | 0.015 (3) |
C7 | 0.129 (4) | 0.093 (3) | 0.103 (3) | 0.034 (3) | 0.048 (3) | 0.031 (3) |
C8 | 0.105 (3) | 0.083 (3) | 0.076 (3) | 0.039 (2) | 0.039 (2) | 0.022 (2) |
C9 | 0.0586 (19) | 0.055 (2) | 0.076 (2) | 0.0179 (16) | 0.0189 (17) | 0.0119 (17) |
C10 | 0.068 (2) | 0.060 (2) | 0.122 (4) | 0.0175 (19) | 0.009 (2) | 0.003 (2) |
C11 | 0.0539 (19) | 0.068 (2) | 0.106 (3) | 0.0099 (17) | 0.0300 (19) | 0.003 (2) |
C12 | 0.0462 (18) | 0.0548 (19) | 0.081 (2) | 0.0000 (15) | 0.0196 (17) | −0.0013 (17) |
C13 | 0.0489 (17) | 0.0574 (18) | 0.0630 (19) | 0.0078 (15) | 0.0055 (15) | 0.0010 (15) |
C14 | 0.061 (2) | 0.079 (2) | 0.071 (2) | 0.0017 (19) | 0.0173 (17) | 0.0084 (19) |
C15 | 0.061 (2) | 0.072 (2) | 0.102 (3) | −0.0088 (19) | 0.015 (2) | 0.015 (2) |
C16 | 0.059 (2) | 0.060 (2) | 0.091 (3) | −0.0033 (17) | −0.0026 (19) | −0.005 (2) |
C17 | 0.078 (3) | 0.091 (3) | 0.073 (3) | 0.011 (2) | 0.005 (2) | −0.018 (2) |
C18 | 0.095 (3) | 0.138 (4) | 0.068 (3) | 0.023 (3) | 0.028 (2) | −0.003 (3) |
C19 | 0.077 (3) | 0.109 (3) | 0.089 (3) | 0.007 (2) | 0.033 (2) | 0.016 (3) |
C20 | 0.063 (2) | 0.076 (2) | 0.073 (2) | −0.0056 (18) | 0.0153 (18) | 0.0029 (19) |
C21 | 0.0485 (17) | 0.0523 (17) | 0.0614 (19) | 0.0034 (14) | 0.0073 (14) | 0.0002 (15) |
C22 | 0.0572 (19) | 0.060 (2) | 0.066 (2) | 0.0059 (16) | 0.0038 (16) | −0.0040 (16) |
C23 | 0.0571 (19) | 0.072 (2) | 0.0639 (19) | 0.0090 (17) | 0.0069 (16) | −0.0058 (17) |
C24 | 0.0563 (18) | 0.0602 (19) | 0.0531 (18) | 0.0007 (16) | 0.0134 (15) | 0.0040 (15) |
C25 | 0.065 (2) | 0.074 (2) | 0.083 (3) | 0.0026 (19) | 0.0019 (19) | −0.005 (2) |
C26 | 0.088 (3) | 0.087 (3) | 0.078 (2) | −0.004 (2) | 0.020 (2) | −0.003 (2) |
C27 | 0.079 (3) | 0.076 (3) | 0.105 (3) | −0.006 (2) | 0.030 (2) | −0.002 (2) |
C28 | 0.066 (2) | 0.094 (3) | 0.085 (3) | −0.013 (2) | 0.0201 (19) | −0.024 (2) |
C29 | 0.062 (2) | 0.088 (3) | 0.088 (3) | −0.0053 (19) | 0.0233 (19) | −0.021 (2) |
O1—C12 | 1.237 (3) | C14—C15 | 1.394 (5) |
O2—C12 | 1.268 (4) | C14—H14A | 0.9300 |
O2—H2B | 0.8200 | C15—C16 | 1.349 (5) |
O3—C24 | 1.196 (3) | C15—H15A | 0.9300 |
O4—C24 | 1.322 (4) | C16—C22 | 1.411 (5) |
O4—H4B | 0.8200 | C16—H16A | 0.9300 |
N1—C25 | 1.484 (4) | C17—C18 | 1.348 (5) |
N1—C29 | 1.491 (4) | C17—C22 | 1.413 (5) |
N1—H1A | 0.9001 | C17—H17A | 0.9300 |
C1—C2 | 1.381 (5) | C18—C19 | 1.401 (6) |
C1—C9 | 1.403 (4) | C18—H18A | 0.9300 |
C1—C11 | 1.496 (5) | C19—C20 | 1.361 (5) |
C2—C3 | 1.438 (7) | C19—H19A | 0.9300 |
C2—H2A | 0.9300 | C20—C21 | 1.408 (4) |
C3—C4 | 1.371 (7) | C20—H20A | 0.9300 |
C3—H3A | 0.9300 | C21—C22 | 1.415 (4) |
C4—C10 | 1.366 (6) | C23—C24 | 1.500 (4) |
C4—H4A | 0.9300 | C23—H23A | 0.9700 |
C5—C6 | 1.357 (6) | C23—H23B | 0.9700 |
C5—C10 | 1.460 (6) | C25—C26 | 1.501 (5) |
C5—H5A | 0.9300 | C25—H25A | 0.9700 |
C6—C7 | 1.378 (6) | C25—H25B | 0.9700 |
C6—H6A | 0.9300 | C26—C27 | 1.511 (5) |
C7—C8 | 1.335 (5) | C26—H26A | 0.9700 |
C7—H7A | 0.9300 | C26—H26B | 0.9700 |
C8—C9 | 1.444 (5) | C27—C28 | 1.502 (5) |
C8—H8A | 0.9300 | C27—H27A | 0.9700 |
C9—C10 | 1.381 (5) | C27—H27B | 0.9700 |
C11—C12 | 1.524 (4) | C28—C29 | 1.510 (4) |
C11—H11A | 0.9700 | C28—H28A | 0.9700 |
C11—H11B | 0.9700 | C28—H28B | 0.9700 |
C13—C14 | 1.367 (4) | C29—H29A | 0.9700 |
C13—C21 | 1.436 (4) | C29—H29B | 0.9700 |
C13—C23 | 1.496 (4) | ||
C12—O2—H2B | 109.5 | C18—C17—H17A | 119.2 |
C24—O4—H4B | 109.5 | C22—C17—H17A | 119.2 |
C25—N1—C29 | 111.8 (3) | C17—C18—C19 | 119.9 (4) |
C25—N1—H1A | 108.6 | C17—C18—H18A | 120.1 |
C29—N1—H1A | 108.7 | C19—C18—H18A | 120.1 |
C2—C1—C9 | 116.3 (4) | C20—C19—C18 | 120.4 (4) |
C2—C1—C11 | 121.7 (4) | C20—C19—H19A | 119.8 |
C9—C1—C11 | 121.8 (3) | C18—C19—H19A | 119.8 |
C1—C2—C3 | 121.3 (4) | C19—C20—C21 | 121.0 (4) |
C1—C2—H2A | 119.4 | C19—C20—H20A | 119.5 |
C3—C2—H2A | 119.4 | C21—C20—H20A | 119.5 |
C4—C3—C2 | 118.1 (4) | C20—C21—C22 | 118.7 (3) |
C4—C3—H3A | 120.9 | C20—C21—C13 | 122.5 (3) |
C2—C3—H3A | 120.9 | C22—C21—C13 | 118.8 (3) |
C10—C4—C3 | 122.4 (5) | C16—C22—C17 | 121.9 (3) |
C10—C4—H4A | 118.8 | C16—C22—C21 | 119.7 (3) |
C3—C4—H4A | 118.8 | C17—C22—C21 | 118.4 (3) |
C6—C5—C10 | 115.3 (5) | C13—C23—C24 | 115.5 (3) |
C6—C5—H5A | 122.3 | C13—C23—H23A | 108.4 |
C10—C5—H5A | 122.3 | C24—C23—H23A | 108.4 |
C5—C6—C7 | 125.4 (5) | C13—C23—H23B | 108.4 |
C5—C6—H6A | 117.3 | C24—C23—H23B | 108.4 |
C7—C6—H6A | 117.3 | H23A—C23—H23B | 107.5 |
C8—C7—C6 | 118.6 (5) | O3—C24—O4 | 123.3 (3) |
C8—C7—H7A | 120.7 | O3—C24—C23 | 126.1 (3) |
C6—C7—H7A | 120.7 | O4—C24—C23 | 110.6 (3) |
C7—C8—C9 | 121.7 (4) | N1—C25—C26 | 110.4 (3) |
C7—C8—H8A | 119.1 | N1—C25—H25A | 109.6 |
C9—C8—H8A | 119.1 | C26—C25—H25A | 109.6 |
C10—C9—C1 | 123.8 (4) | N1—C25—H25B | 109.6 |
C10—C9—C8 | 117.6 (4) | C26—C25—H25B | 109.6 |
C1—C9—C8 | 118.6 (3) | H25A—C25—H25B | 108.1 |
C4—C10—C9 | 118.0 (5) | C25—C26—C27 | 111.3 (3) |
C4—C10—C5 | 120.8 (5) | C25—C26—H26A | 109.4 |
C9—C10—C5 | 121.2 (4) | C27—C26—H26A | 109.4 |
C1—C11—C12 | 112.9 (3) | C25—C26—H26B | 109.4 |
C1—C11—H11A | 109.0 | C27—C26—H26B | 109.4 |
C12—C11—H11A | 109.0 | H26A—C26—H26B | 108.0 |
C1—C11—H11B | 109.0 | C28—C27—C26 | 110.3 (3) |
C12—C11—H11B | 109.0 | C28—C27—H27A | 109.6 |
H11A—C11—H11B | 107.8 | C26—C27—H27A | 109.6 |
O1—C12—O2 | 123.8 (3) | C28—C27—H27B | 109.6 |
O1—C12—C11 | 118.4 (3) | C26—C27—H27B | 109.6 |
O2—C12—C11 | 117.7 (3) | H27A—C27—H27B | 108.1 |
C14—C13—C21 | 118.5 (3) | C27—C28—C29 | 111.9 (3) |
C14—C13—C23 | 119.7 (3) | C27—C28—H28A | 109.2 |
C21—C13—C23 | 121.7 (3) | C29—C28—H28A | 109.2 |
C13—C14—C15 | 122.1 (3) | C27—C28—H28B | 109.2 |
C13—C14—H14A | 118.9 | C29—C28—H28B | 109.2 |
C15—C14—H14A | 118.9 | H28A—C28—H28B | 107.9 |
C16—C15—C14 | 120.6 (3) | N1—C29—C28 | 109.6 (3) |
C16—C15—H15A | 119.7 | N1—C29—H29A | 109.8 |
C14—C15—H15A | 119.7 | C28—C29—H29A | 109.8 |
C15—C16—C22 | 120.2 (3) | N1—C29—H29B | 109.8 |
C15—C16—H16A | 119.9 | C28—C29—H29B | 109.8 |
C22—C16—H16A | 119.9 | H29A—C29—H29B | 108.2 |
C18—C17—C22 | 121.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.90 | 1.85 | 2.736 (3) | 168 |
O2—H2B···N1 | 0.82 | 1.94 | 2.759 (3) | 175 |
O4—H4B···O2 | 0.82 | 1.77 | 2.578 (3) | 166 |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | 2C12H10O2·C5H11N |
Mr | 457.55 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 9.7415 (16), 19.174 (3), 13.6232 (19) |
β (°) | 105.757 (11) |
V (Å3) | 2449.0 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.4 × 0.3 × 0.2 |
Data collection | |
Diffractometer | Bruker P4 |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5745, 4550, 2552 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.137, 1.05 |
No. of reflections | 4550 |
No. of parameters | 309 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.56, −0.27 |
Computer programs: XSCANS (Bruker, 1997a), XSCANS, SHELXTL (Bruker, 1997b), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.90 | 1.85 | 2.736 (3) | 168.3 |
O2—H2B···N1 | 0.82 | 1.94 | 2.759 (3) | 174.5 |
O4—H4B···O2 | 0.82 | 1.77 | 2.578 (3) | 166.4 |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Numerous highly efficient nonlinear optical (NLO) crystals for visible and ultraviolet (UV) regions have been synthesized and studied. They attract considerable attention due to their extreme importance for both laser spectroscopy and laser processing (Prasad & Williams, 1991; Pal et al., 2003). In recent years, many new non-linear optical second harmonic generation (SHG) materials of organic adduct were reported, which have main merits. The main advantage of organic adduct materials compared with inorganic materials for such second-harmonic generation devices are the large macroscopic second-order nonlinear optical susceptibilities, ultrafast optical response time and high optical damage thresholds (Anwar et al., 2000; Muthuraman et al., 2001; Kotler et al., 1992; Wang et al., 2006). At present, adduct assembly is a hot point in designing solid state structures with outstanding conductance, electronic, nonlinear optical or magnetic properties (Brasselet et al., 1999; Rodrigues et al., 2001; Goswami et al., 1999). We report herein the synthesis and structure of a new organic adduct of 1-naphthalene-acetic acid and piperidine.
The asymmetric unit of the title compound, (I), contains two naphthalene-acetic acid and one piperidine moieties (Fig. 1), in which they are held together by intramolecular O—H···O and O—H···N hydrogen bonds (Table 1). The bond lengths and angles are generally within normal ranges (Allen et al., 1987). The two oxygen atoms of each carboxyl groups are conjugated [O1—C12 =1.237 (3) Å, O2—C12 = 1.268 (4) Å and O3—C24 = 1.196 (3) Å, O4—C24 1.322 (4) Å].
Rings A (C1—C10) and B (C13—C22) are, of course, planar and the dihedral angle between them is A/B = 14.20 (2)°. Ring C (N1/C25—C29) is not planar, having total puckering amplitude, QT, of 0.568 (3) Å, and chair conformation [φ = 1.36 (3)° and θ = 1.39 (3)°] (Cremer & Pople, 1975).
In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into dimers (Fig. 2), in which they seem to be effective in the stabilization of the structure.