3-[(2-Hydroxy­ethyl)imino­meth­yl]-1,1′-bi-2-naphthol

Zhang, Y.; Wang, K.; Zhong, L.-Z.; Li, R.-X.

doi:10.1107/S1600536809016407

organic compounds

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Volume 65| Part 6| June 2009| Page o1226

doi:10.1107/S1600536809016407

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3-[(2-Hydroxyethyl)iminomethyl]-1,1′-bi-2-naphthol

Yu Zhang,^a Kun Wang,^a Ling-Zhi Zhong ^a and Rui-Xiang Li ^a ^*

^aInstitute of Homogeneous Catalysis, Department of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
^*Correspondence e-mail: sculiruixiang@gmail.com

(Received 27 April 2009; accepted 1 May 2009; online 7 May 2009)

In the title compound, C₂₃H₁₉NO₃, there is an intramolecular O—H⋯N hydrogen bond, which forms a six-membered ring, and intermolecular O—H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For background on the application of salen complexes to asymmetric catalysis, see: Pu (1998 ). For the synthesis of the title compound, see: Chin et al. (2004 ).

Experimental

Crystal data

C₂₃H₁₉NO₃
M_r = 357.39
Orthorhombic, P b c a
a = 12.6184 (3) Å
b = 9.7774 (2) Å
c = 29.7991 (6) Å
V = 3676.47 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.50 × 0.40 × 0.36 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.661, T_max = 1.000 (expected range = 0.641–0.970)
24940 measured reflections
4220 independent reflections
1912 reflections with I > 2σ(I)
R_int = 0.089

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.135
S = 1.00
4220 reflections
252 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3ⁱ	0.82	1.87	2.6638 (17)	161
O3—H3A⋯O1ⁱⁱ	0.82	2.05	2.7724 (17)	147
O1—H1⋯N1	0.96 (2)	1.67 (2)	2.5649 (18)	153 (2)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016407/bt2938sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016407/bt2938Isup2.hkl

checkCIF report

Comment top

BINOL and its derivatives have been largely used in asymmetric catalysis and chiral recognition (Pu, 1998). In this paper we present X-ray crystallographic analysis of the title compound (I), as the continuation of our previous studies.

As shown in Figure 1, an intramolecular O—H···N hydrogen bond between the hydroxy and the imino moieties forms a ring.

In the crystal, the molecules are connected by O—H···O hydrogen bonds ( Fig. 2).

Related literature top

For background on the application of salen complexes to asymmetric catalysis, see: Pu (1998). For the synthesis of the title compound, see: Chin et al. (2004).

Experimental top

The salen ligand,

3-((2-hydroxyethylimino)methyl)-1,1'-binaphthol was prepared by condensation of 3-carboxaldehyde-1,1'-binaphthol with 2-aminoethanol. Crystals suitable for X-ray analysis were obtained by slow evaporation of a ethanol /methylene chloride (1:5) solution of the compound.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A perspective view of the title compound.
	Fig. 2. Intermolecular hydrogen bonding in the crystal structure of (I).

3-[(2-Hydroxyethyl)iminomethyl]-1,1'-bi-2-naphthol top

Crystal data top

C₂₃H₁₉NO₃	D_x = 1.291 Mg m⁻³
M_r = 357.39	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 3454 reflections
a = 12.6184 (3) Å	θ = 2.7–22.4°
b = 9.7774 (2) Å	µ = 0.09 mm⁻¹
c = 29.7991 (6) Å	T = 296 K
V = 3676.47 (14) Å³	Block, red
Z = 8	0.50 × 0.40 × 0.36 mm
F(000) = 1504

Data collection top

Bruker SMART CCD area-detector diffractometer	4220 independent reflections
Radiation source: fine-focus sealed tube	1912 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.089
ϕ and ω scans	θ_max = 27.6°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −15→16
T_min = 0.661, T_max = 1.000	k = −12→12
24940 measured reflections	l = −38→38

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0475P)²] where P = (F_o² + 2F_c²)/3
4220 reflections	(Δ/σ)_max < 0.001
252 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₃H₁₉NO₃	V = 3676.47 (14) Å³
M_r = 357.39	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.6184 (3) Å	µ = 0.09 mm⁻¹
b = 9.7774 (2) Å	T = 296 K
c = 29.7991 (6) Å	0.50 × 0.40 × 0.36 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4220 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1912 reflections with I > 2σ(I)
T_min = 0.661, T_max = 1.000	R_int = 0.089
24940 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.15 e Å⁻³
4220 reflections	Δρ_min = −0.14 e Å⁻³
252 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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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	0.50545 (11)	0.24608 (12)	0.43973 (4)	0.0661 (4)
H1	0.5349 (18)	0.278 (2)	0.4675 (8)	0.109 (8)*
O2	0.31307 (9)	−0.02597 (13)	0.38718 (4)	0.0615 (4)
H2A	0.2483	−0.0321	0.3860	0.092*
O3	0.60553 (9)	0.53599 (13)	0.59680 (4)	0.0647 (4)
H3A	0.5790	0.6125	0.5963	0.097*
N1	0.60154 (12)	0.25597 (15)	0.51551 (4)	0.0528 (4)
C1	0.54441 (13)	0.11749 (16)	0.43397 (5)	0.0423 (5)
C2	0.52157 (13)	0.04833 (17)	0.39500 (5)	0.0406 (4)
C3	0.56310 (13)	−0.08531 (17)	0.38917 (5)	0.0424 (5)
C4	0.54263 (15)	−0.16310 (18)	0.35028 (6)	0.0572 (6)
H4A	0.5016	−0.1255	0.3275	0.069*
C5	0.58156 (16)	−0.2919 (2)	0.34540 (7)	0.0696 (6)
H5A	0.5678	−0.3406	0.3192	0.083*
C6	0.64219 (16)	−0.3519 (2)	0.37943 (7)	0.0710 (6)
H6A	0.6673	−0.4407	0.3761	0.085*
C7	0.66425 (15)	−0.28066 (19)	0.41715 (7)	0.0617 (6)
H7A	0.7059	−0.3207	0.4393	0.074*
C8	0.62541 (13)	−0.14683 (17)	0.42360 (6)	0.0445 (5)
C9	0.64473 (13)	−0.07085 (18)	0.46275 (6)	0.0478 (5)
H9A	0.6848	−0.1104	0.4855	0.057*
C10	0.60711 (12)	0.05847 (17)	0.46872 (5)	0.0392 (4)
C11	0.62936 (13)	0.13284 (19)	0.51008 (5)	0.0452 (5)
H11A	0.6693 (11)	0.0826 (15)	0.5322 (5)	0.044 (4)*
C12	0.62678 (15)	0.32605 (17)	0.55768 (5)	0.0530 (5)
H12A	0.7029	0.3270	0.5623	0.064*
H12B	0.5943	0.2783	0.5827	0.064*
C13	0.58577 (14)	0.46884 (18)	0.55525 (6)	0.0549 (5)
H13A	0.6207	0.5177	0.5311	0.066*
H13B	0.5102	0.4677	0.5492	0.066*
C14	0.45087 (14)	0.11281 (17)	0.36073 (5)	0.0432 (5)
C15	0.34642 (14)	0.07470 (18)	0.35878 (5)	0.0472 (5)
C16	0.27531 (15)	0.1368 (2)	0.32883 (6)	0.0590 (6)
H16A	0.2046	0.1099	0.3283	0.071*
C17	0.31035 (17)	0.2365 (2)	0.30064 (6)	0.0650 (6)
H17A	0.2626	0.2782	0.2812	0.078*
C18	0.41683 (16)	0.27781 (19)	0.30024 (6)	0.0549 (5)
C19	0.45588 (19)	0.3789 (2)	0.27067 (6)	0.0702 (6)
H19A	0.4092	0.4217	0.2510	0.084*
C20	0.5592 (2)	0.4152 (2)	0.27016 (6)	0.0761 (7)
H20A	0.5832	0.4811	0.2501	0.091*
C21	0.62985 (19)	0.3531 (2)	0.29999 (6)	0.0734 (7)
H21A	0.7009	0.3783	0.2997	0.088*
C22	0.59561 (16)	0.25552 (19)	0.32973 (6)	0.0593 (6)
H22A	0.6437	0.2160	0.3495	0.071*
C23	0.48854 (15)	0.21437 (18)	0.33073 (5)	0.0478 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0975 (10)	0.0520 (8)	0.0489 (8)	0.0232 (7)	−0.0257 (8)	−0.0095 (6)
O2	0.0562 (8)	0.0747 (9)	0.0536 (8)	−0.0005 (7)	0.0008 (6)	0.0132 (7)
O3	0.0730 (8)	0.0630 (8)	0.0579 (8)	0.0175 (7)	−0.0196 (7)	−0.0187 (7)
N1	0.0659 (10)	0.0540 (10)	0.0385 (9)	0.0022 (8)	−0.0086 (8)	−0.0029 (7)
C1	0.0485 (10)	0.0401 (10)	0.0382 (10)	0.0048 (8)	0.0000 (9)	0.0015 (8)
C2	0.0447 (10)	0.0445 (10)	0.0325 (9)	0.0024 (8)	−0.0005 (8)	−0.0010 (8)
C3	0.0442 (10)	0.0481 (11)	0.0350 (10)	0.0015 (8)	0.0035 (8)	−0.0005 (8)
C4	0.0661 (13)	0.0612 (13)	0.0442 (11)	0.0094 (10)	0.0003 (10)	−0.0067 (10)
C5	0.0841 (15)	0.0675 (14)	0.0571 (13)	0.0148 (11)	0.0012 (12)	−0.0223 (11)
C6	0.0750 (14)	0.0562 (13)	0.0816 (15)	0.0182 (11)	−0.0013 (13)	−0.0155 (11)
C7	0.0581 (12)	0.0565 (12)	0.0704 (14)	0.0155 (10)	−0.0078 (11)	−0.0059 (11)
C8	0.0423 (10)	0.0461 (10)	0.0450 (10)	0.0051 (8)	−0.0011 (9)	−0.0022 (9)
C9	0.0427 (10)	0.0554 (11)	0.0454 (11)	0.0046 (9)	−0.0074 (9)	0.0066 (9)
C10	0.0424 (9)	0.0431 (10)	0.0322 (9)	0.0011 (8)	0.0007 (8)	0.0040 (8)
C11	0.0480 (10)	0.0522 (11)	0.0355 (10)	0.0006 (9)	−0.0055 (9)	0.0067 (9)
C12	0.0664 (12)	0.0519 (11)	0.0407 (11)	−0.0016 (10)	−0.0094 (10)	−0.0035 (9)
C13	0.0604 (12)	0.0573 (12)	0.0471 (11)	0.0057 (9)	−0.0105 (10)	−0.0088 (9)
C14	0.0518 (10)	0.0497 (11)	0.0282 (9)	0.0076 (8)	−0.0024 (8)	−0.0025 (8)
C15	0.0534 (11)	0.0523 (11)	0.0359 (10)	0.0084 (9)	0.0005 (9)	0.0014 (9)
C16	0.0555 (12)	0.0790 (14)	0.0426 (10)	0.0097 (10)	−0.0091 (10)	0.0000 (10)
C17	0.0763 (14)	0.0760 (14)	0.0425 (11)	0.0176 (11)	−0.0132 (11)	0.0057 (10)
C18	0.0778 (14)	0.0557 (12)	0.0312 (10)	0.0066 (10)	−0.0039 (10)	−0.0003 (9)
C19	0.1052 (17)	0.0666 (14)	0.0390 (12)	0.0089 (12)	−0.0046 (12)	0.0044 (10)
C20	0.1250 (19)	0.0609 (14)	0.0425 (12)	−0.0102 (13)	0.0083 (13)	0.0062 (10)
C21	0.0907 (16)	0.0754 (15)	0.0542 (13)	−0.0164 (12)	0.0142 (12)	−0.0060 (12)
C22	0.0715 (13)	0.0649 (13)	0.0414 (11)	−0.0009 (10)	0.0031 (11)	−0.0015 (10)
C23	0.0616 (12)	0.0521 (11)	0.0297 (10)	0.0056 (9)	0.0017 (9)	−0.0043 (9)

Geometric parameters (Å, º) top

O1—C1	1.3609 (19)	C10—C11	1.458 (2)
O1—H1	0.96 (2)	C11—H11A	0.964 (14)
O2—C15	1.3646 (19)	C12—C13	1.491 (2)
O2—H2A	0.8200	C12—H12A	0.9700
O3—C13	1.423 (2)	C12—H12B	0.9700
O3—H3A	0.8200	C13—H13A	0.9700
N1—C11	1.264 (2)	C13—H13B	0.9700
N1—C12	1.466 (2)	C14—C15	1.371 (2)
C1—C2	1.374 (2)	C14—C23	1.418 (2)
C1—C10	1.425 (2)	C15—C16	1.404 (2)
C2—C3	1.418 (2)	C16—C17	1.361 (3)
C2—C14	1.495 (2)	C16—H16A	0.9300
C3—C4	1.410 (2)	C17—C18	1.403 (3)
C3—C8	1.426 (2)	C17—H17A	0.9300
C4—C5	1.360 (3)	C18—C19	1.413 (3)
C4—H4A	0.9300	C18—C23	1.425 (2)
C5—C6	1.399 (3)	C19—C20	1.352 (3)
C5—H5A	0.9300	C19—H19A	0.9300
C6—C7	1.351 (3)	C20—C21	1.398 (3)
C6—H6A	0.9300	C20—H20A	0.9300
C7—C8	1.410 (2)	C21—C22	1.372 (3)
C7—H7A	0.9300	C21—H21A	0.9300
C8—C9	1.404 (2)	C22—C23	1.410 (3)
C9—C10	1.362 (2)	C22—H22A	0.9300
C9—H9A	0.9300

C1—O1—H1	105.5 (13)	N1—C12—H12B	109.9
C15—O2—H2A	109.5	C13—C12—H12B	109.9
C13—O3—H3A	109.5	H12A—C12—H12B	108.3
C11—N1—C12	119.62 (14)	O3—C13—C12	109.21 (14)
O1—C1—C2	119.04 (15)	O3—C13—H13A	109.8
O1—C1—C10	118.87 (14)	C12—C13—H13A	109.8
C2—C1—C10	122.08 (15)	O3—C13—H13B	109.8
C1—C2—C3	118.63 (15)	C12—C13—H13B	109.8
C1—C2—C14	119.65 (15)	H13A—C13—H13B	108.3
C3—C2—C14	121.68 (14)	C15—C14—C23	119.07 (15)
C4—C3—C2	121.99 (15)	C15—C14—C2	119.20 (15)
C4—C3—C8	117.70 (15)	C23—C14—C2	121.71 (15)
C2—C3—C8	120.29 (15)	O2—C15—C14	117.79 (15)
C5—C4—C3	121.41 (17)	O2—C15—C16	120.60 (16)
C5—C4—H4A	119.3	C14—C15—C16	121.60 (17)
C3—C4—H4A	119.3	C17—C16—C15	119.64 (18)
C4—C5—C6	120.56 (18)	C17—C16—H16A	120.2
C4—C5—H5A	119.7	C15—C16—H16A	120.2
C6—C5—H5A	119.7	C16—C17—C18	121.51 (18)
C7—C6—C5	119.96 (19)	C16—C17—H17A	119.2
C7—C6—H6A	120.0	C18—C17—H17A	119.2
C5—C6—H6A	120.0	C17—C18—C19	122.73 (18)
C6—C7—C8	121.33 (18)	C17—C18—C23	118.52 (17)
C6—C7—H7A	119.3	C19—C18—C23	118.75 (19)
C8—C7—H7A	119.3	C20—C19—C18	121.8 (2)
C9—C8—C7	122.93 (16)	C20—C19—H19A	119.1
C9—C8—C3	118.05 (15)	C18—C19—H19A	119.1
C7—C8—C3	119.02 (16)	C19—C20—C21	119.6 (2)
C10—C9—C8	122.62 (16)	C19—C20—H20A	120.2
C10—C9—H9A	118.7	C21—C20—H20A	120.2
C8—C9—H9A	118.7	C22—C21—C20	120.8 (2)
C9—C10—C1	118.31 (15)	C22—C21—H21A	119.6
C9—C10—C11	120.41 (15)	C20—C21—H21A	119.6
C1—C10—C11	121.27 (15)	C21—C22—C23	120.92 (19)
N1—C11—C10	121.97 (16)	C21—C22—H22A	119.5
N1—C11—H11A	122.9 (9)	C23—C22—H22A	119.5
C10—C11—H11A	115.1 (9)	C22—C23—C14	122.30 (16)
N1—C12—C13	108.70 (14)	C22—C23—C18	118.10 (17)
N1—C12—H12A	109.9	C14—C23—C18	119.61 (17)
C13—C12—H12A	109.9

O1—C1—C2—C3	179.60 (15)	C11—N1—C12—C13	179.82 (16)
C10—C1—C2—C3	−0.8 (2)	N1—C12—C13—O3	177.37 (14)
O1—C1—C2—C14	−2.7 (2)	C1—C2—C14—C15	−99.84 (19)
C10—C1—C2—C14	176.94 (15)	C3—C2—C14—C15	77.8 (2)
C1—C2—C3—C4	179.57 (16)	C1—C2—C14—C23	78.9 (2)
C14—C2—C3—C4	1.9 (2)	C3—C2—C14—C23	−103.43 (19)
C1—C2—C3—C8	1.2 (2)	C23—C14—C15—O2	178.20 (14)
C14—C2—C3—C8	−176.48 (15)	C2—C14—C15—O2	−3.0 (2)
C2—C3—C4—C5	−178.97 (17)	C23—C14—C15—C16	−2.0 (3)
C8—C3—C4—C5	−0.6 (3)	C2—C14—C15—C16	176.74 (15)
C3—C4—C5—C6	0.9 (3)	O2—C15—C16—C17	−179.66 (16)
C4—C5—C6—C7	−1.3 (3)	C14—C15—C16—C17	0.6 (3)
C5—C6—C7—C8	1.4 (3)	C15—C16—C17—C18	1.0 (3)
C6—C7—C8—C9	178.55 (18)	C16—C17—C18—C19	178.59 (18)
C6—C7—C8—C3	−1.0 (3)	C16—C17—C18—C23	−1.0 (3)
C4—C3—C8—C9	−179.00 (15)	C17—C18—C19—C20	−178.56 (19)
C2—C3—C8—C9	−0.6 (2)	C23—C18—C19—C20	1.0 (3)
C4—C3—C8—C7	0.6 (2)	C18—C19—C20—C21	−1.0 (3)
C2—C3—C8—C7	179.02 (16)	C19—C20—C21—C22	0.2 (3)
C7—C8—C9—C10	179.89 (17)	C20—C21—C22—C23	0.6 (3)
C3—C8—C9—C10	−0.5 (2)	C21—C22—C23—C14	179.33 (17)
C8—C9—C10—C1	1.0 (2)	C21—C22—C23—C18	−0.5 (3)
C8—C9—C10—C11	179.91 (15)	C15—C14—C23—C22	−177.84 (16)
O1—C1—C10—C9	179.33 (15)	C2—C14—C23—C22	3.4 (3)
C2—C1—C10—C9	−0.3 (2)	C15—C14—C23—C18	2.0 (2)
O1—C1—C10—C11	0.4 (2)	C2—C14—C23—C18	−176.76 (15)
C2—C1—C10—C11	−179.21 (15)	C17—C18—C23—C22	179.31 (17)
C12—N1—C11—C10	−179.51 (15)	C19—C18—C23—C22	−0.3 (3)
C9—C10—C11—N1	175.33 (16)	C17—C18—C23—C14	−0.5 (3)
C1—C10—C11—N1	−5.7 (3)	C19—C18—C23—C14	179.91 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3ⁱ	0.82	1.87	2.6638 (17)	161
O3—H3A···O1ⁱⁱ	0.82	2.05	2.7724 (17)	147
O1—H1···N1	0.96 (2)	1.67 (2)	2.5649 (18)	153 (2)

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₉NO₃
M_r	357.39
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	12.6184 (3), 9.7774 (2), 29.7991 (6)
V (Å³)	3676.47 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.40 × 0.36

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.661, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	24940, 4220, 1912
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.135, 1.00
No. of reflections	4220
No. of parameters	252
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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
O2—H2A···O3ⁱ	0.82	1.87	2.6638 (17)	161.4
O3—H3A···O1ⁱⁱ	0.82	2.05	2.7724 (17)	146.9
O1—H1···N1	0.96 (2)	1.67 (2)	2.5649 (18)	153 (2)

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+1, −y+1, −z+1.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chin, J., Kim, D. C., Kim, H. J., Francis, B. P. & Kim, K. M. (2004). Org. Lett. 6, 2591–2593. Web of Science CrossRef PubMed CAS Google Scholar
Pu, L. (1998). Chem. Rev. 98, 2405–2494. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 6| June 2009| Page o1226

doi:10.1107/S1600536809016407

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