1-Naphthalene­acetic acid–piperidine (2/1)

Wang, Z.; Yin, Q.; Zou, R.-Y.; Wang, R.-J.; Zhao, Y.-F.

doi:10.1107/S1600536807036719

1-Naphthaleneacetic acid–piperidine (2/1)

Z. Wang, Q. Yin, R.-Y. Zou, R.-J. Wang and Y.-F. Zhao

The asymmetric unit of the title compound, 2C₁₂H₁₀O₂·C₅H₁₁N, contains two naphthaleneacetic acid molecules and one piperidine molecule, which are held together by intermolecular O—H

O and O—H

N hydrogen bonds. The piperidine ring has a chair conformation. In the crystal structure, intermolecular N—H

O hydrogen bonds link the molecules into dimers.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036719/hk2300sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036719/hk2300Isup2.hkl Contains datablock I

CCDC reference: 657883

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.006 Å
R factor = 0.064
wR factor = 0.137
Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C6     -   C7      ..       7.68 su

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.05
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C24
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

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, Q_T, 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.

Related literature top

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).

Experimental top

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).

Structure description top

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.

Computing details top

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.

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 35% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines [symmetry code (#1): 2 - x, 1 - y, 1 - z].

1-Naphthaleneacetic acid–piperidine (2/1) top

Crystal data top

2C₁₂H₁₀O₂·C₅H₁₁N	F(000) = 976
M_r = 457.55	D_x = 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

Data collection top

Bruker P4 diffractometer	R_int = 0.034
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 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 top

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(F_o²) + (0.001P)² + 2P] where P = (F_o² + 2F_c²)/3
4550 reflections	(Δ/σ)_max < 0.001
309 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

2C₁₂H₁₀O₂·C₅H₁₁N	V = 2449.0 (7) Å³
M_r = 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)°

Data collection top

Bruker P4 diffractometer	R_int = 0.034
5745 measured reflections	3 standard reflections every 97 reflections
4550 independent reflections	intensity decay: none
2552 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.05	Δρ_max = 0.56 e Å⁻³
4550 reflections	Δρ_min = −0.27 e Å⁻³
309 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.27

Computer programs: XSCANS (Bruker, 1997a), XSCANS, SHELXTL (Bruker, 1997b), SHELXTL.