(R)-1,1′-Binaphthalene-2,2′-diol–(Z)-N-ethyl­ideneethanamine N-oxide (1/1)

Shao, B.; Wang, H.-B.

doi:10.1107/S1600536812007477

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o948

doi:10.1107/S1600536812007477

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(R)-1,1′-Binaphthalene-2,2′-diol–(Z)-N-ethylideneethanamine N-oxide (1/1)

Bo Shao ^a and Hai-Bin Wang ^b ^*

^aCollege of Biology and Environmental Engineering, Zhejiang Shuren University, Hangzhou 310015, People's Republic of China, and ^bCollege of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: zgdwhb@sina.com

(Received 17 December 2011; accepted 19 February 2012; online 3 March 2012)

In the title compound, C₄H₉NO·C₂₀H₁₄O₂, the dihedral angle between the naphthalene ring systems of the binaphthalenediol molecule is 77.53 (14)°. In the crystal, the two components are linked by O—H⋯O hydrogen bonds, forming a zigzag chain along the c axis.

Related literature

For applications of 2,2′-dihydroxy-1,1′-dinaphthalene in asymmetric synthesis, see: Noyori et al. (1984 ); Reeder et al. (1994 ); Toda et al. (1989 ); Zhang & Schuster (1994 ). For related literature on oxidation of hydroxylamines to nitrones, see: Cicchi et al. (2001 ); Engel et al. (1997 ); Liu et al. (2004 ).

Experimental

Crystal data

C₄H₉NO·C₂₀H₁₄O₂
M_r = 373.43
Trigonal, P 3₁
a = 8.9579 (6) Å
c = 21.187 (3) Å
V = 1472.4 (2) Å³
Z = 3
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 273 K
0.31 × 0.22 × 0.18 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.964, T_max = 0.977
7771 measured reflections
1732 independent reflections
1662 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.115
S = 1.19
1732 reflections
257 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.82	1.90	2.706 (5)	167
O2—H2⋯O3ⁱ	0.82	1.96	2.763 (5)	168
Symmetry code: (i) $[-x+y, -x+1, z-{\script{1\over 3}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812007477/is5033sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007477/is5033Isup2.hkl

checkCIF report

Comment top

2,2'-Dihydroxy-1,1'-dinaphthalene (binaphthol) is an important chemical as a precursor for catalysis in asymmetric synthesis, as a chiral host for molecular recognition and enantiomer separation and also as intermediates for the synthesis of chiral materials (Noyori et al., 1984; Toda et al., 1989; Reeder et al., 1994; Zhang & Schuster, 1994). N,N-diethylhydroxylamine is easily oxidized to form E and Z type of N-ethylideneethanamine N-oxide (ELDEA) (Engel et al., 1997; Liu et al., 2004; Cicchi et al., 2001). In this study, only the Z type of ELDEA is trapped by the (R)-binaphthol to form the title complex, (I) (Scheme 1 and Fig. 1).

The asymmetric unit comprises a ELDEA (Z type) molecule and a (R)-binaphthol molecule, which are linked by an intermolecular O—H···O hydrogen bond (Table 1). The two naphthyl groups are almost perpendicular to each other with a dihedral angle being 77.53 (14)°. The N1—O3 length [1.313 (5) Å] of ELDEA is characteristic of the N—O single bond, while the N1═C22 bond [1.265 (7) Å] is a double bond. Because of the existence of N1═C22 double bond, the O3/N1/C21/C22/C24 plane is almost planar. The ELDEA is connected to two H atoms from different binaphthol molecules through O—H···O hydrogen bonds (Fig. 2 and Table 1), forming infinite chains running along the c axis.

Related literature top

For applications of 2,2'-dihydroxy-1,1'-dinaphthalene in asymmetric synthesis, see: Noyori et al. (1984); Reeder et al. (1994); Toda et al. (1989); Zhang & Schuster (1994). For related literature on oxidation of hydroxylamines to nitrones, see: Cicchi et al. (2001); Engel et al. (1997); Liu et al. (2004).

Experimental top

The (R)-1,1'-bi-2-naphthol (2.9 g) and N,N-diethylhydroxylamine (0.9 g) were mixed and dissolved in sufficient ethanol 30 ml by heating to a temperature of 353 K where a clear solution was resulted, then refluxed for 5 h. The materials of experiment were exposed in air. Single crystals of (I) (2.7 g) were formed form an ethanol solution by gradual evaporation for two weeks at room temperature.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom-labeling and displacement ellipsoids drawn at the 40% probability level. The hydrogen bond is illustrated as a dashed line.
	Fig. 2. A crystal packing diagram of the title compound, viewed along the b axis. Hydrogen bonds are drawn as dashed lines.

(R)-1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol– (Z)-N-ethylethanimine N-oxide (1/1) top

Crystal data top

C₄H₉NO·C₂₀H₁₄O₂	D_x = 1.263 Mg m⁻³
M_r = 373.43	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3₁	Cell parameters from 1360 reflections
Hall symbol: P 31	θ = 2.4–16.6°
a = 8.9579 (6) Å	µ = 0.08 mm⁻¹
c = 21.187 (3) Å	T = 273 K
V = 1472.4 (2) Å³	Prism, colorless
Z = 3	0.31 × 0.22 × 0.18 mm
F(000) = 594.0

Data collection top

Bruker APEX area-detector diffractometer	1732 independent reflections
Radiation source: fine-focus sealed tube	1662 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scan	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→9
T_min = 0.964, T_max = 0.977	k = −7→10
7771 measured reflections	l = −25→25

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0471P)² + 0.4671P] where P = (F_o² + 2F_c²)/3
1732 reflections	(Δ/σ)_max < 0.001
257 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₄H₉NO·C₂₀H₁₄O₂	Z = 3
M_r = 373.43	Mo Kα radiation
Trigonal, P3₁	µ = 0.08 mm⁻¹
a = 8.9579 (6) Å	T = 273 K
c = 21.187 (3) Å	0.31 × 0.22 × 0.18 mm
V = 1472.4 (2) Å³

Data collection top

Bruker APEX area-detector diffractometer	1732 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1662 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.977	R_int = 0.033
7771 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	1 restraint
wR(F²) = 0.115	H-atom parameters constrained
S = 1.19	Δρ_max = 0.19 e Å⁻³
1732 reflections	Δρ_min = −0.26 e Å⁻³
257 parameters

Special details top

Experimental. The IR (KBr pellet) spectrum of (I) showed bands: 3069, 1624, 1583, 1504, 1433, 1338, 1275, 1241, 1177, 1142, 1093, 1012, 979, 965, 928, 867, 820, 753, 624, 581, 492, 442 and 424 cm^-1.

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	0.6567 (4)	0.7994 (4)	0.76094 (13)	0.0418 (7)
H1	0.5835	0.7851	0.7872	0.063*
O2	0.5514 (4)	0.5899 (4)	0.59216 (14)	0.0500 (8)
H2	0.5018	0.5977	0.5609	0.075*
O3	0.3797 (4)	0.7314 (5)	0.83262 (16)	0.0582 (9)
N1	0.2490 (6)	0.5834 (6)	0.8144 (2)	0.0643 (12)
C1	0.7392 (4)	0.6275 (4)	0.70313 (16)	0.0255 (7)
C2	0.6670 (5)	0.6537 (5)	0.75628 (16)	0.0308 (8)
C3	0.6065 (5)	0.5327 (5)	0.80628 (17)	0.0365 (9)
H3A	0.5573	0.5521	0.8417	0.044*
C4	0.6198 (5)	0.3880 (5)	0.80293 (17)	0.0356 (9)
H4	0.5799	0.3100	0.8363	0.043*
C5	0.6929 (5)	0.3548 (5)	0.74984 (19)	0.0344 (9)
C6	0.7057 (6)	0.2039 (6)	0.7449 (2)	0.0472 (11)
H6	0.6660	0.1247	0.7778	0.057*
C7	0.7742 (7)	0.1731 (6)	0.6935 (2)	0.0551 (12)
H7	0.7819	0.0735	0.6911	0.066*
C8	0.8336 (7)	0.2911 (6)	0.6437 (2)	0.0510 (12)
H8	0.8796	0.2686	0.6080	0.061*
C9	0.8253 (5)	0.4385 (5)	0.64668 (18)	0.0370 (9)
H9	0.8674	0.5161	0.6132	0.044*
C10	0.7537 (4)	0.4758 (5)	0.69961 (17)	0.0292 (8)
C11	0.8048 (5)	0.7566 (4)	0.65051 (16)	0.0266 (8)
C12	0.7106 (5)	0.7323 (5)	0.59651 (17)	0.0323 (9)
C13	0.7759 (5)	0.8506 (5)	0.54687 (18)	0.0411 (10)
H13	0.7108	0.8299	0.5104	0.049*
C14	0.9330 (5)	0.9954 (5)	0.55105 (18)	0.0399 (10)
H14	0.9747	1.0715	0.5172	0.048*
C15	1.0329 (5)	1.0315 (5)	0.60593 (19)	0.0342 (9)
C16	1.1919 (6)	1.1874 (6)	0.6136 (2)	0.0464 (11)
H16	1.2330	1.2674	0.5810	0.056*
C17	1.2848 (6)	1.2220 (6)	0.6673 (2)	0.0562 (13)
H17	1.3878	1.3256	0.6718	0.067*
C18	1.2245 (6)	1.1009 (6)	0.7159 (2)	0.0579 (13)
H18	1.2897	1.1232	0.7525	0.069*
C19	1.0714 (5)	0.9500 (6)	0.71080 (19)	0.0413 (10)
H19	1.0337	0.8720	0.7441	0.050*
C20	0.9695 (5)	0.9104 (5)	0.65601 (17)	0.0288 (8)
C21	0.2757 (9)	0.6739 (10)	0.7052 (3)	0.094 (2)
H21A	0.3380	0.6372	0.6785	0.140*
H21B	0.3534	0.7868	0.7215	0.140*
H21C	0.1865	0.6772	0.6812	0.140*
C22	0.1986 (8)	0.5529 (9)	0.7577 (3)	0.0802 (18)
H22	0.1050	0.4449	0.7486	0.096*
C23	0.0453 (10)	0.4797 (11)	0.9012 (4)	0.110 (3)
H23A	−0.0384	0.4820	0.8735	0.165*
H23B	0.1082	0.5886	0.9225	0.165*
H23C	−0.0123	0.3896	0.9318	0.165*
C24	0.1635 (9)	0.4481 (9)	0.8648 (3)	0.093 (2)
H24A	0.1012	0.3351	0.8454	0.112*
H24B	0.2505	0.4498	0.8925	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0524 (18)	0.0364 (15)	0.0433 (17)	0.0272 (14)	0.0132 (13)	0.0028 (12)
O2	0.0400 (16)	0.0387 (17)	0.0457 (18)	0.0005 (13)	−0.0158 (13)	0.0099 (13)
O3	0.057 (2)	0.067 (2)	0.055 (2)	0.0340 (19)	0.0085 (16)	−0.0168 (16)
N1	0.055 (3)	0.072 (3)	0.057 (3)	0.025 (2)	0.007 (2)	−0.006 (2)
C1	0.0221 (17)	0.0219 (18)	0.0266 (17)	0.0067 (15)	−0.0059 (15)	−0.0002 (14)
C2	0.0277 (19)	0.032 (2)	0.033 (2)	0.0144 (17)	−0.0027 (15)	0.0006 (15)
C3	0.042 (2)	0.045 (2)	0.0238 (19)	0.0221 (19)	0.0043 (16)	0.0013 (16)
C4	0.041 (2)	0.035 (2)	0.028 (2)	0.0174 (18)	0.0057 (17)	0.0098 (17)
C5	0.032 (2)	0.030 (2)	0.038 (2)	0.0134 (17)	−0.0003 (17)	0.0037 (16)
C6	0.061 (3)	0.035 (2)	0.048 (3)	0.026 (2)	0.006 (2)	0.0130 (19)
C7	0.078 (3)	0.042 (3)	0.058 (3)	0.040 (3)	0.011 (3)	0.006 (2)
C8	0.071 (3)	0.048 (3)	0.045 (3)	0.038 (3)	0.011 (2)	−0.002 (2)
C9	0.045 (2)	0.036 (2)	0.033 (2)	0.0229 (19)	0.0051 (17)	0.0049 (17)
C10	0.0246 (18)	0.0260 (19)	0.032 (2)	0.0093 (15)	−0.0003 (15)	0.0000 (15)
C11	0.0305 (19)	0.0234 (18)	0.0277 (18)	0.0148 (16)	0.0031 (15)	0.0026 (14)
C12	0.032 (2)	0.028 (2)	0.032 (2)	0.0116 (17)	−0.0026 (16)	−0.0003 (16)
C13	0.045 (2)	0.043 (2)	0.030 (2)	0.018 (2)	−0.0035 (18)	0.0063 (18)
C14	0.045 (2)	0.040 (2)	0.029 (2)	0.017 (2)	0.0055 (18)	0.0156 (18)
C15	0.031 (2)	0.029 (2)	0.040 (2)	0.0129 (17)	0.0030 (17)	0.0030 (16)
C16	0.039 (2)	0.037 (2)	0.052 (3)	0.0106 (19)	0.008 (2)	0.0136 (19)
C17	0.033 (2)	0.040 (2)	0.067 (3)	−0.003 (2)	−0.007 (2)	0.003 (2)
C18	0.041 (3)	0.049 (3)	0.058 (3)	0.003 (2)	−0.016 (2)	0.005 (2)
C19	0.039 (2)	0.041 (2)	0.035 (2)	0.0126 (19)	−0.0064 (17)	0.0014 (17)
C20	0.0285 (19)	0.0288 (19)	0.032 (2)	0.0168 (16)	0.0016 (16)	−0.0009 (15)
C21	0.076 (4)	0.149 (6)	0.058 (3)	0.057 (5)	−0.007 (3)	0.016 (4)
C22	0.055 (3)	0.097 (5)	0.070 (4)	0.025 (3)	−0.012 (3)	−0.021 (4)
C23	0.095 (5)	0.110 (6)	0.119 (6)	0.047 (5)	0.032 (5)	0.033 (5)
C24	0.092 (5)	0.087 (5)	0.088 (5)	0.035 (4)	0.024 (4)	0.014 (4)

Geometric parameters (Å, º) top

O1—C2	1.357 (4)	C12—C13	1.397 (5)
O1—H1	0.8200	C13—C14	1.358 (6)
O2—C12	1.360 (5)	C13—H13	0.9300
O2—H2	0.8200	C14—C15	1.403 (6)
O3—N1	1.313 (5)	C14—H14	0.9300
N1—C22	1.265 (7)	C15—C20	1.417 (5)
N1—C24	1.506 (8)	C15—C16	1.420 (6)
C1—C2	1.376 (5)	C16—C17	1.351 (6)
C1—C10	1.431 (5)	C16—H16	0.9300
C1—C11	1.498 (5)	C17—C18	1.394 (7)
C2—C3	1.416 (5)	C17—H17	0.9300
C3—C4	1.361 (6)	C18—C19	1.366 (6)
C3—H3A	0.9300	C18—H18	0.9300
C4—C5	1.406 (6)	C19—C20	1.408 (5)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.416 (6)	C21—C22	1.463 (9)
C5—C10	1.419 (5)	C21—H21A	0.9600
C6—C7	1.345 (6)	C21—H21B	0.9600
C6—H6	0.9300	C21—H21C	0.9600
C7—C8	1.397 (7)	C22—H22	0.9300
C7—H7	0.9300	C23—C24	1.447 (10)
C8—C9	1.361 (6)	C23—H23A	0.9600
C8—H8	0.9300	C23—H23B	0.9600
C9—C10	1.412 (5)	C23—H23C	0.9600
C9—H9	0.9300	C24—H24A	0.9700
C11—C12	1.373 (5)	C24—H24B	0.9700
C11—C20	1.434 (5)

C2—O1—H1	109.5	C12—C13—H13	119.4
C12—O2—H2	109.5	C13—C14—C15	120.7 (3)
C22—N1—O3	122.6 (5)	C13—C14—H14	119.6
C22—N1—C24	121.1 (5)	C15—C14—H14	119.6
O3—N1—C24	116.3 (4)	C14—C15—C20	118.6 (3)
C2—C1—C10	118.6 (3)	C14—C15—C16	122.2 (4)
C2—C1—C11	120.9 (3)	C20—C15—C16	119.2 (4)
C10—C1—C11	120.5 (3)	C17—C16—C15	121.5 (4)
O1—C2—C1	119.2 (3)	C17—C16—H16	119.2
O1—C2—C3	119.9 (3)	C15—C16—H16	119.2
C1—C2—C3	120.9 (3)	C16—C17—C18	119.3 (4)
C4—C3—C2	120.5 (3)	C16—C17—H17	120.4
C4—C3—H3A	119.7	C18—C17—H17	120.4
C2—C3—H3A	119.7	C19—C18—C17	121.2 (4)
C3—C4—C5	121.0 (3)	C19—C18—H18	119.4
C3—C4—H4	119.5	C17—C18—H18	119.4
C5—C4—H4	119.5	C18—C19—C20	121.2 (4)
C4—C5—C6	122.0 (4)	C18—C19—H19	119.4
C4—C5—C10	118.7 (3)	C20—C19—H19	119.4
C6—C5—C10	119.3 (4)	C19—C20—C15	117.6 (4)
C7—C6—C5	121.3 (4)	C19—C20—C11	122.3 (3)
C7—C6—H6	119.4	C15—C20—C11	120.1 (3)
C5—C6—H6	119.4	C22—C21—H21A	109.5
C6—C7—C8	119.8 (4)	C22—C21—H21B	109.5
C6—C7—H7	120.1	H21A—C21—H21B	109.5
C8—C7—H7	120.1	C22—C21—H21C	109.5
C9—C8—C7	120.9 (4)	H21A—C21—H21C	109.5
C9—C8—H8	119.5	H21B—C21—H21C	109.5
C7—C8—H8	119.5	N1—C22—C21	125.2 (6)
C8—C9—C10	121.2 (4)	N1—C22—H22	117.4
C8—C9—H9	119.4	C21—C22—H22	117.4
C10—C9—H9	119.4	C24—C23—H23A	109.5
C9—C10—C5	117.4 (3)	C24—C23—H23B	109.5
C9—C10—C1	122.3 (3)	H23A—C23—H23B	109.5
C5—C10—C1	120.3 (3)	C24—C23—H23C	109.5
C12—C11—C20	118.4 (3)	H23A—C23—H23C	109.5
C12—C11—C1	121.7 (3)	H23B—C23—H23C	109.5
C20—C11—C1	120.0 (3)	C23—C24—N1	110.4 (6)
O2—C12—C11	118.6 (3)	C23—C24—H24A	109.6
O2—C12—C13	120.4 (3)	N1—C24—H24A	109.6
C11—C12—C13	121.1 (3)	C23—C24—H24B	109.6
C14—C13—C12	121.1 (4)	N1—C24—H24B	109.6
C14—C13—H13	119.4	H24A—C24—H24B	108.1

C10—C1—C2—O1	178.3 (3)	C20—C11—C12—O2	−177.4 (3)
C11—C1—C2—O1	−0.5 (5)	C1—C11—C12—O2	2.2 (5)
C10—C1—C2—C3	−0.6 (5)	C20—C11—C12—C13	2.7 (5)
C11—C1—C2—C3	−179.4 (3)	C1—C11—C12—C13	−177.7 (3)
O1—C2—C3—C4	−178.4 (4)	O2—C12—C13—C14	178.5 (4)
C1—C2—C3—C4	0.5 (6)	C11—C12—C13—C14	−1.6 (6)
C2—C3—C4—C5	−0.3 (6)	C12—C13—C14—C15	−1.0 (6)
C3—C4—C5—C6	−179.0 (4)	C13—C14—C15—C20	2.4 (6)
C3—C4—C5—C10	0.3 (6)	C13—C14—C15—C16	−175.4 (4)
C4—C5—C6—C7	179.2 (5)	C14—C15—C16—C17	178.4 (5)
C10—C5—C6—C7	−0.1 (7)	C20—C15—C16—C17	0.7 (7)
C5—C6—C7—C8	−0.2 (8)	C15—C16—C17—C18	1.0 (8)
C6—C7—C8—C9	0.8 (8)	C16—C17—C18—C19	−1.7 (8)
C7—C8—C9—C10	−1.1 (7)	C17—C18—C19—C20	0.6 (8)
C8—C9—C10—C5	0.8 (6)	C18—C19—C20—C15	1.1 (6)
C8—C9—C10—C1	−178.3 (4)	C18—C19—C20—C11	−177.2 (4)
C4—C5—C10—C9	−179.5 (4)	C14—C15—C20—C19	−179.5 (4)
C6—C5—C10—C9	−0.2 (5)	C16—C15—C20—C19	−1.7 (5)
C4—C5—C10—C1	−0.5 (5)	C14—C15—C20—C11	−1.2 (5)
C6—C5—C10—C1	178.9 (4)	C16—C15—C20—C11	176.6 (4)
C2—C1—C10—C9	179.7 (3)	C12—C11—C20—C19	177.0 (4)
C11—C1—C10—C9	−1.6 (5)	C1—C11—C20—C19	−2.7 (5)
C2—C1—C10—C5	0.6 (5)	C12—C11—C20—C15	−1.2 (5)
C11—C1—C10—C5	179.4 (3)	C1—C11—C20—C15	179.1 (3)
C2—C1—C11—C12	−100.6 (4)	O3—N1—C22—C21	0.1 (10)
C10—C1—C11—C12	80.6 (4)	C24—N1—C22—C21	−178.4 (6)
C2—C1—C11—C20	79.0 (4)	C22—N1—C24—C23	−100.9 (8)
C10—C1—C11—C20	−99.7 (4)	O3—N1—C24—C23	80.5 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.82	1.90	2.706 (5)	167
O2—H2···O3ⁱ	0.82	1.96	2.763 (5)	168

Symmetry code: (i) −x+y, −x+1, z−1/3.

Experimental details

Crystal data
Chemical formula	C₄H₉NO·C₂₀H₁₄O₂
M_r	373.43
Crystal system, space group	Trigonal, P3₁
Temperature (K)	273
a, c (Å)	8.9579 (6), 21.187 (3)
V (Å³)	1472.4 (2)
Z	3
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.31 × 0.22 × 0.18

Data collection
Diffractometer	Bruker APEX area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.964, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	7771, 1732, 1662
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.115, 1.19
No. of reflections	1732
No. of parameters	257
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.26

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.82	1.90	2.706 (5)	167
O2—H2···O3ⁱ	0.82	1.96	2.763 (5)	168

Symmetry code: (i) −x+y, −x+1, z−1/3.

Acknowledgements

The authors thank Mr X.-J. Ma for preparing the sample, and Mr X.-J. Ma and Mr H.-Y. Li for collecting the diffraction data.

References

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