Ethyl 2-(4-hydr­oxy-1-methyl-2-oxo-1,2-dihydro­quinolin-3-yl)acetate

Ukrainets, I.V.; Shishkina, S.V.; Shishkin, O.V.; Davidenko, A.A.; Tkach, A.A.

doi:10.1107/S1600536809011921

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o968

doi:10.1107/S1600536809011921

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Ethyl 2-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)acetate

Igor V. Ukrainets,^a ^* Svetlana V. Shishkina,^b Oleg V. Shishkin,^b Alexandra A. Davidenko ^a and Andrei A. Tkach ^a

^aNational University of Pharmacy, 4 Blyukhera ave., Kharkiv 61002, Ukraine, and ^bSTC "Institute for Single Crystals", National Academy of Sciences of Ukraine, 60 Lenina ave., Kharkiv 61001, Ukraine
^*Correspondence e-mail: uiv@kharkov.ua

(Received 20 March 2009; accepted 31 March 2009; online 8 April 2009)

In the title compound, C₁₄H₁₅NO₄, the bicyclic fragment and the ester group form a dihedral angle of 86.7 (2)°. Intermolecular O—H⋯O and C—H⋯O hydrogen bonding connects molecules into a helix along the crystallographic b axis.

Related literature

For esters of 4-hydroxy-2-oxo-1,2-dihydroquinolin-3-acetic acids as non-steroidal anti-inflammatory drugs, see: Ukrainets et al. (2001 ). For their use in the synthesis of natural alkaloids, see: Ramesh & Shanmugam (1985 ); Geismann & Cho (1959 ) and in highly active antithyroid substances, see: Ukrainets et al. (1997 ). For van der Waals radii, see: Zefirov (1997 ). For related structures, see: Jurd et al. (1983 ); Ukrainets et al. (2000 ). For bond-length data, see: Bürgi & Dunitz (1994 ).

Experimental

Crystal data

C₁₄H₁₅NO₄
M_r = 261.27
Monoclinic, C 2/c
a = 21.608 (2) Å
b = 9.2155 (9) Å
c = 14.6795 (12) Å
β = 119.632 (9)°
V = 2540.8 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur3 diffractometer
Absorption correction: none
13114 measured reflections
2862 independent reflections
2376 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.171
S = 1.19
2862 reflections
232 parameters
All H-atom parameters refined
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1ⁱ	0.95 (3)	1.71 (3)	2.649 (2)	169 (2)
C10—H10a⋯O1ⁱ	0.94 (2)	2.34 (3)	3.235 (2)	159 (2)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: XP (Siemens, 1998 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011921/kp2212sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809011921/kp2212Isup2.hkl

checkCIF report

Comment top

Esters of 4-hydroxy-2-oxo-1,2-dihydroquinolin-3-acetic acids can be considered as non-steroid anti-inflammatory drugs (Ukrainets et al., 2001). However they are of great interest for synthesis of natural alkaloids (Ramesh & Shanmugam, 1985; Geismann & Cho, 1959) and highly active antithyroid substances (Ukrainets et al., 1997). In the present paper, we report the crystal structure of the (4-hydroxy-1-methyl-2-oxo-1,2-dihydro- quinolin-3-yl)-acetic acid ethyl ester (I) (Fig. 1). The bicyclic fragment and the C14, O1, C10 and O2 atoms are coplanar within 0.02 Å. The planar ester group at the C10 atom has orthogonal orientation with respect to the plane of quinolone bicycle (the C7—C8—C10—C11 torsion angle is 90.8 (2) %A) whereas the C8—C10—C11—O3 torsion angle is 7.3 (3) %A). The C9—O1 bond (1.250 (2) Å) is elongated as compared with its mean value (1.210 Å; Bürgi & Dunitz, 1994) owing to the formation of the intermolecular hydrogen bond O2—H2O···O1' (Table 1). The presence of hydrogen bond affects the orientation of the hydrogen atom of hydroxy group despite of strong repulsion with hydrogen atom of neighbouring methylene group: distance H10a···H2O is 2.09 Å [the van der Waals radii sum is 2.34 Å (Zefirov, 1997)]. It should be noted that the C7—O2 bond length (1.341 (2) Å) is close to its mean value 1.333 Å observed in earlier investigated compounds (Jurd et al., 1983; Ukrainets et al., 2000). In the crystal the molecules form the infinite helix along the [0 1 0] direction (Fig. 2) via the O2—H2O···O1 intermolecular hydrogen bond between hydroxyl group of one molecule and carbonyl group of quinolone fragment of neighbouring molecule. The C10—H10a···O1' intermolecular hydrogen bond (Table 1) occurs as well.

Related literature top

For ssters of 4-hydroxy-2-oxo-1,2-dihydroquinolin-3-acetic acids as non-steroidal anti-inflammatory drugs, see: Ukrainets et al. (2001). For their use in the synthesis of natural alkaloids, see: Ramesh & Shanmugam (1985); Geismann & Cho (1959) and in highly active antithyroid substances, see: Ukrainets et al. (1997). For van der Waals radii, see: Zefirov (1997). For related structures, see: Jurd et al. (1983); Ukrainets et al. (2000). For bond-length data, see: Bürgi & Dunitz (1994).

Experimental top

(4-Hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-acetic acid is synthesized from the methyl N-methyl anthranilate using the known method (Geismann & Cho, 1959) and then is esterified by ethanol (Ukrainets et al., 2001). Yield 96%. M.p. 454–457 K.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED (Oxford Diffraction, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP (Siemens, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title compound with atomic numbering. All atoms are shown with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The packing of the molecules in a crystal. The hydrogen bonds are shown by dashed lines.

Ethyl 2-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)acetate top

Crystal data top

C₁₄H₁₅NO₄	D_x = 1.366 Mg m⁻³
M_r = 261.27	Melting point: 455 K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.608 (2) Å	Cell parameters from 8736 reflections
b = 9.2155 (9) Å	θ = 4–32°
c = 14.6795 (12) Å	µ = 0.10 mm⁻¹
β = 119.632 (9)°	T = 293 K
V = 2540.8 (4) Å³	Block, colourless
Z = 8	0.30 × 0.30 × 0.20 mm
F(000) = 1104

Data collection top

Oxford Diffraction Xcalibur3 diffractometer	2376 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	R_int = 0.030
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
Detector resolution: 16.1827 pixels mm^-1	h = −28→28
ω scans	k = −11→11
13114 measured reflections	l = −19→19
2862 independent reflections

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)] = 0.060	Hydrogen site location: difference Fourier map
wR(F²) = 0.171	All H-atom parameters refined
S = 1.19	w = 1/[σ²(F_o²) + (0.0943P)²] where P = (F_o² + 2F_c²)/3
2862 reflections	(Δ/σ)_max < 0.001
232 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₄H₁₅NO₄	V = 2540.8 (4) Å³
M_r = 261.27	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.608 (2) Å	µ = 0.10 mm⁻¹
b = 9.2155 (9) Å	T = 293 K
c = 14.6795 (12) Å	0.30 × 0.30 × 0.20 mm
β = 119.632 (9)°

Data collection top

Oxford Diffraction Xcalibur3 diffractometer	2376 reflections with I > 2σ(I)
13114 measured reflections	R_int = 0.030
2862 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.171	All H-atom parameters refined
S = 1.19	Δρ_max = 0.28 e Å⁻³
2862 reflections	Δρ_min = −0.19 e Å⁻³
232 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
N1	0.12615 (8)	0.48562 (16)	0.00279 (10)	0.0447 (4)
O1	0.23317 (6)	0.38519 (13)	0.11389 (9)	0.0511 (4)
O2	0.14804 (7)	0.78108 (14)	0.22763 (10)	0.0528 (4)
H2O	0.1932 (14)	0.807 (3)	0.284 (2)	0.086 (8)*
O3	0.21567 (7)	0.39416 (16)	0.34316 (11)	0.0651 (4)
O4	0.32312 (6)	0.48690 (14)	0.45168 (9)	0.0525 (4)
C1	0.07158 (8)	0.58298 (18)	−0.01697 (12)	0.0434 (4)
C2	0.00694 (10)	0.5816 (2)	−0.11336 (15)	0.0566 (5)
H2	0.0020 (13)	0.511 (3)	−0.161 (2)	0.077 (7)*
C3	−0.04624 (10)	0.6786 (3)	−0.13061 (17)	0.0652 (6)
H3	−0.0931 (15)	0.677 (3)	−0.195 (2)	0.102 (9)*
C4	−0.03752 (10)	0.7799 (3)	−0.05606 (18)	0.0638 (6)
H4	−0.0737 (14)	0.850 (3)	−0.064 (2)	0.087 (7)*
C5	0.02492 (9)	0.7826 (2)	0.03876 (16)	0.0541 (5)
H5	0.0334 (10)	0.852 (2)	0.0948 (15)	0.054 (5)*
C6	0.07974 (8)	0.68292 (17)	0.05940 (13)	0.0419 (4)
C7	0.14509 (8)	0.68166 (17)	0.15888 (12)	0.0393 (4)
C8	0.19716 (8)	0.58370 (17)	0.17776 (12)	0.0390 (4)
C9	0.18749 (9)	0.47940 (18)	0.09900 (12)	0.0407 (4)
C10	0.26583 (8)	0.57643 (19)	0.28059 (12)	0.0413 (4)
H10B	0.3055 (9)	0.5445 (19)	0.2663 (13)	0.042 (4)*
H10A	0.2774 (9)	0.668 (2)	0.3117 (14)	0.044 (5)*
C11	0.26352 (8)	0.47532 (18)	0.35929 (13)	0.0416 (4)
C12	0.32854 (11)	0.3976 (2)	0.53692 (15)	0.0564 (5)
H12B	0.2882 (13)	0.416 (3)	0.5450 (19)	0.082 (7)*
H12A	0.3291 (12)	0.291 (3)	0.5182 (18)	0.084 (7)*
C13	0.39738 (15)	0.4393 (3)	0.63283 (17)	0.0757 (7)
H13C	0.3974 (17)	0.546 (4)	0.658 (2)	0.132 (12)*
H13B	0.4378 (17)	0.416 (4)	0.623 (3)	0.119 (11)*
H13A	0.4017 (15)	0.380 (3)	0.688 (2)	0.105 (9)*
C14	0.11943 (14)	0.3847 (3)	−0.07860 (17)	0.0627 (5)
H14C	0.1113 (13)	0.444 (3)	−0.1404 (19)	0.084 (7)*
H14B	0.1627 (16)	0.332 (3)	−0.050 (2)	0.105 (10)*
H14A	0.0770 (14)	0.324 (3)	−0.0999 (19)	0.080 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0472 (8)	0.0479 (8)	0.0323 (7)	−0.0083 (6)	0.0145 (6)	0.0011 (6)
O1	0.0542 (7)	0.0477 (7)	0.0450 (7)	0.0045 (5)	0.0196 (6)	0.0028 (5)
O2	0.0436 (7)	0.0519 (7)	0.0528 (7)	−0.0003 (5)	0.0160 (6)	−0.0072 (6)
O3	0.0505 (8)	0.0751 (10)	0.0550 (8)	−0.0127 (6)	0.0149 (6)	0.0126 (7)
O4	0.0458 (7)	0.0627 (8)	0.0352 (6)	0.0027 (5)	0.0095 (5)	0.0072 (5)
C1	0.0368 (8)	0.0472 (9)	0.0359 (8)	−0.0093 (7)	0.0101 (7)	0.0112 (7)
C2	0.0476 (10)	0.0667 (13)	0.0378 (9)	−0.0157 (9)	0.0075 (8)	0.0124 (9)
C3	0.0387 (10)	0.0794 (15)	0.0531 (11)	−0.0089 (9)	0.0040 (8)	0.0275 (11)
C4	0.0373 (10)	0.0654 (13)	0.0707 (13)	0.0015 (9)	0.0129 (9)	0.0215 (11)
C5	0.0400 (9)	0.0511 (11)	0.0597 (11)	−0.0004 (8)	0.0159 (8)	0.0127 (9)
C6	0.0345 (8)	0.0410 (9)	0.0417 (8)	−0.0051 (6)	0.0123 (7)	0.0121 (7)
C7	0.0356 (8)	0.0383 (8)	0.0380 (8)	−0.0068 (6)	0.0137 (6)	0.0032 (6)
C8	0.0356 (8)	0.0384 (8)	0.0337 (8)	−0.0037 (6)	0.0100 (6)	0.0046 (6)
C9	0.0420 (9)	0.0398 (8)	0.0356 (8)	−0.0045 (6)	0.0156 (7)	0.0050 (6)
C10	0.0340 (8)	0.0394 (9)	0.0380 (9)	−0.0014 (6)	0.0084 (7)	−0.0008 (6)
C11	0.0365 (8)	0.0442 (9)	0.0372 (8)	0.0059 (6)	0.0128 (7)	−0.0017 (6)
C12	0.0600 (12)	0.0693 (14)	0.0412 (10)	0.0198 (9)	0.0259 (9)	0.0129 (9)
C13	0.0800 (17)	0.0909 (19)	0.0360 (10)	0.0189 (14)	0.0134 (10)	0.0088 (11)
C14	0.0691 (14)	0.0706 (14)	0.0398 (10)	−0.0091 (11)	0.0204 (10)	−0.0092 (10)

Geometric parameters (Å, º) top

N1—C9	1.380 (2)	C5—H5	0.98 (2)
N1—C1	1.393 (2)	C6—C7	1.445 (2)
N1—C14	1.463 (3)	C7—C8	1.360 (2)
O1—C9	1.250 (2)	C8—C9	1.437 (2)
O2—C7	1.341 (2)	C8—C10	1.507 (2)
O2—H2O	0.95 (3)	C10—C11	1.504 (2)
O3—C11	1.201 (2)	C10—H10B	1.021 (18)
O4—C11	1.335 (2)	C10—H10A	0.935 (19)
O4—C12	1.453 (2)	C12—C13	1.507 (3)
C1—C6	1.393 (2)	C12—H12B	0.95 (2)
C1—C2	1.414 (2)	C12—H12A	1.02 (3)
C2—C3	1.377 (3)	C13—H13C	1.05 (4)
C2—H2	0.92 (3)	C13—H13B	0.98 (3)
C3—C4	1.378 (3)	C13—H13A	0.94 (3)
C3—H3	0.99 (3)	C14—H14C	1.00 (3)
C4—C5	1.379 (3)	C14—H14B	0.95 (3)
C4—H4	0.97 (3)	C14—H14A	0.98 (3)
C5—C6	1.409 (2)

C9—N1—C1	121.71 (14)	O1—C9—C8	122.39 (14)
C9—N1—C14	117.82 (16)	N1—C9—C8	118.67 (14)
C1—N1—C14	120.46 (16)	C11—C10—C8	114.00 (13)
C7—O2—H2O	118.5 (15)	C11—C10—H10B	109.2 (10)
C11—O4—C12	117.13 (15)	C8—C10—H10B	108.6 (10)
C6—C1—N1	120.06 (14)	C11—C10—H10A	106.7 (11)
C6—C1—C2	118.72 (17)	C8—C10—H10A	110.0 (10)
N1—C1—C2	121.21 (17)	H10B—C10—H10A	108.2 (14)
C3—C2—C1	120.0 (2)	O3—C11—O4	123.65 (16)
C3—C2—H2	123.1 (16)	O3—C11—C10	125.92 (15)
C1—C2—H2	116.8 (16)	O4—C11—C10	110.43 (14)
C2—C3—C4	121.30 (18)	O4—C12—C13	106.40 (19)
C2—C3—H3	122.3 (17)	O4—C12—H12B	108.5 (15)
C4—C3—H3	116.4 (16)	C13—C12—H12B	112.4 (14)
C3—C4—C5	119.7 (2)	O4—C12—H12A	108.7 (14)
C3—C4—H4	124.4 (15)	C13—C12—H12A	111.0 (13)
C5—C4—H4	115.9 (16)	H12B—C12—H12A	110 (2)
C4—C5—C6	120.3 (2)	C12—C13—H13C	113.3 (18)
C4—C5—H5	122.7 (11)	C12—C13—H13B	110 (2)
C6—C5—H5	117.1 (11)	H13C—C13—H13B	114 (3)
C1—C6—C5	119.99 (15)	C12—C13—H13A	106.8 (18)
C1—C6—C7	118.66 (14)	H13C—C13—H13A	105 (3)
C5—C6—C7	121.36 (17)	H13B—C13—H13A	107 (3)
O2—C7—C8	124.99 (14)	N1—C14—H14C	107.4 (15)
O2—C7—C6	114.46 (14)	N1—C14—H14B	106.9 (18)
C8—C7—C6	120.53 (15)	H14C—C14—H14B	112 (2)
C7—C8—C9	120.23 (14)	N1—C14—H14A	108.7 (15)
C7—C8—C10	122.64 (15)	H14C—C14—H14A	107.6 (19)
C9—C8—C10	117.11 (14)	H14B—C14—H14A	114 (2)
O1—C9—N1	118.92 (15)

C9—N1—C1—C6	3.6 (2)	O2—C7—C8—C9	178.40 (14)
C14—N1—C1—C6	−177.17 (16)	C6—C7—C8—C9	−0.4 (2)
C9—N1—C1—C2	−175.56 (14)	O2—C7—C8—C10	−0.3 (2)
C14—N1—C1—C2	3.7 (2)	C6—C7—C8—C10	−179.14 (14)
C6—C1—C2—C3	0.5 (2)	C1—N1—C9—O1	176.58 (14)
N1—C1—C2—C3	179.68 (15)	C14—N1—C9—O1	−2.7 (2)
C1—C2—C3—C4	1.1 (3)	C1—N1—C9—C8	−4.7 (2)
C2—C3—C4—C5	−1.5 (3)	C14—N1—C9—C8	176.02 (16)
C3—C4—C5—C6	0.2 (3)	C7—C8—C9—O1	−178.23 (15)
N1—C1—C6—C5	179.10 (14)	C10—C8—C9—O1	0.5 (2)
C2—C1—C6—C5	−1.7 (2)	C7—C8—C9—N1	3.1 (2)
N1—C1—C6—C7	−0.8 (2)	C10—C8—C9—N1	−178.10 (13)
C2—C1—C6—C7	178.41 (14)	C7—C8—C10—C11	90.75 (19)
C4—C5—C6—C1	1.4 (3)	C9—C8—C10—C11	−87.98 (19)
C4—C5—C6—C7	−178.75 (16)	C12—O4—C11—O3	−1.4 (2)
C1—C6—C7—O2	−179.69 (13)	C12—O4—C11—C10	178.93 (15)
C5—C6—C7—O2	0.4 (2)	C8—C10—C11—O3	7.3 (3)
C1—C6—C7—C8	−0.7 (2)	C8—C10—C11—O4	−173.09 (13)
C5—C6—C7—C8	179.38 (15)	C11—O4—C12—C13	−175.83 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1ⁱ	0.95 (3)	1.71 (3)	2.649 (2)	169 (2)
C10—H10a···O1ⁱ	0.94 (2)	2.34 (3)	3.235 (2)	159 (2)

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅NO₄
M_r	261.27
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	21.608 (2), 9.2155 (9), 14.6795 (12)
β (°)	119.632 (9)
V (Å³)	2540.8 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur3 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13114, 2862, 2376
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.171, 1.19
No. of reflections	2862
No. of parameters	232
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.19

Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), SHELXTL (Sheldrick, 2008), XP (Siemens, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1ⁱ	0.95 (3)	1.71 (3)	2.649 (2)	169 (2)
C10—H10a···O1ⁱ	0.94 (2)	2.34 (3)	3.235 (2)	159 (2)

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

References

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Volume 65| Part 5| May 2009| Page o968

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