8-Hydr­oxy-8-phenyl-2,3,7,8-tetra­hydro-6H-1,4-dioxino[2,3-f]isoindol-6-one

Tafeenko, V.A.; Aslanov, L.A.; Khasanov, M.I.; Mochalov, S.S.

doi:10.1107/S1600536808003012

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o548

doi:10.1107/S1600536808003012

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8-Hydroxy-8-phenyl-2,3,7,8-tetrahydro-6H-1,4-dioxino[2,3-f]isoindol-6-one

Viktor A. Tafeenko,^a Leonid A. Aslanov,^a ^* Mahmud I. Khasanov ^a and Sergei S. Mochalov ^a

^aChemistry Department, Moscow State University, 119991 Moscow, Russian Federation
^*Correspondence e-mail: aslanov@struct.chem.msu.ru

(Received 29 December 2007; accepted 28 January 2008; online 6 February 2008)

In the title compound, C₁₆H₁₃NO₄, the indole system is essentially planar, whereas the dioxane ring adopts a twist conformation. The molecules are linked into chains by —O— H⋯O=C— hydrogen bonds and these chains are linked into rods by means of N—H⋯O hydrogen bonds. Exept for weak C—H⋯O interactions between the rods, no other intermolecular contacts of interest are present.

Related literature

For details of the appropriate nitrile hydrolysis, see: Moorthy & Singhal (2005 ).

Experimental

Crystal data

C₁₆H₁₃NO₄
M_r = 283.27
Monoclinic, P 2₁ /c
a = 8.6001 (17) Å
b = 27.005 (5) Å
c = 5.7221 (5) Å
β = 92.602 (10)°
V = 1327.6 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.85 mm⁻¹
T = 291 (2) K
0.08 × 0.06 × 0.04 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
2892 measured reflections
2653 independent reflections
1784 reflections with I > 2σ(I)
R_int = 0.025
2 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.147
S = 1.05
2653 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3ⁱ	0.82	1.95	2.725 (3)	158
N7—H7⋯O2ⁱⁱ	0.86	2.09	2.922 (3)	161
C5—H5⋯O4ⁱⁱⁱ	0.93	2.52	3.404 (3)	160
C19—H19⋯O2	0.93	2.40	2.734 (4)	101
Symmetry codes: (i) x, y, z+1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z+1.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003012/rk2073sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003012/rk2073Isup2.hkl

checkCIF report

Comment top

To investigate mechanisms of intra- and intermolecular reactions of ortho-substituted benzenes we intended to synthesize novel ortho-acyl-substituted benzamides by hydrolysis (Moorthy & Singhal, 2005) of appropriate nitriles. In the case of hydrolysis of 7-benzoyl-2,3-dihydro-1,4-benzodioxine-6-carbonitrile (1) the compound 7-benzoyl-2,3-dihydro-1,4-benzodioxine-6-carboxamide (2) was expected to be produced (Fig. 1). Both the elemental analysis and mass spectroscopic data (M+ 283) of the compound we obtained, were in good agreement with structure (2), but ¹H NMR data were not. Although 13 protons were identified in the ¹H NMR spectrum, an expected signal for the NH₂ group was absent. In addition, two single signals were detected in the ¹H NMR spectrum, each corresponding to one proton of large difference in chemical shift (6.70 and 9.02). To determine the structure of the compound, we carried out an X-ray crystallographic analysis, which revealed that hydrolysis of (1), under the conditions specified by Moorthy & Singhal, did not produce the expected compound (2); instead the product was an isomer of compound (2), viz. 8-hydroxy-8-phenyl-2,3,7,8-tetrahydro-6H-[1,4]dioxino [2,3-f]isoindol-6-one, (3) (Fig. 1).

The dihedral angle between the planes defined by the atoms C5/C9/C10/C11/C12/C13 (plane 1) and C8/N7/C6/C10/C11 (plane 2) (Fig. 2) is 1.64 (9)°. The 6-membered dioxane ring adopts a twist conformation, with atoms C3 and C2 displaced out of plane 1 by 0.375 (4) and -0.273 (3) Å, respectively, compared with displacements of -0.012 (3) and 0.010 (3) Å for O4 and O1, respectively (Fig. 2). The torsion angle O2—C8—C14—C19 has rather a small value [16.7 (3)°]. This results from the intramolecular hydrogen bond C19—H19···O2. The packing motif, as shown in Fig.3, can be described as follows: molecules are linked by hydrogen bonds in head-to-tail fashion through oxy- and keto-groups to form infinite chains. The two adjacent chains are linked by N7—H7···O2ⁱⁱ hydrogen bonds, forming infinite rods running along the c axis. Neighbouring rods interact via centrosymmetric C5—H5···O4ⁱⁱⁱ hydrogen bonds. Symmetry codes are listed in Table 1.

Related literature top

For details of the appropriate nitrile hydrolysis, see: Moorthy & Singhal (2005).

Experimental top

A mixture of (1) (1 g, 0.0038 mol), concentrated sulfuric acid (1 ml) and trifluoroacetic acid (4 ml) was boiled under reflux. with stirring, for 5 h. The solution was then poured into ice-water (75 ml). The resulting white precipitate was filtered off, washed with water and recrystallized from acetone.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Hydrolysis of (1) did not produce the expected compound, (2) but rather an isomer of (2), viz. compound (3).
	Fig. 2. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. The dashed line indicates an intramolecular hydrogen bond.
	Fig. 3. The packing motif of the crystal structure. Hydrogen atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity. Symmetry codes: (i) x, y, z + 1; (ii) x, -y + 3/2, z - 1/2; (iii) -x, -y + 1, -z + 1.

8-Hydroxy-8-phenyl-2,3,7,8-tetrahydro-6H-1,4-dioxino[2,3-f]isoindol-6-one top

Crystal data top

C₁₆H₁₃NO₄	F(000) = 592
M_r = 283.27	D_x = 1.417 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 485–486 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 8.6001 (17) Å	Cell parameters from 25 reflections
b = 27.005 (5) Å	θ = 26–42°
c = 5.7221 (5) Å	µ = 0.85 mm⁻¹
β = 92.602 (10)°	T = 291 K
V = 1327.6 (4) Å³	Prism, colorless
Z = 4	0.08 × 0.06 × 0.04 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.025
Radiation source: fine-focus sealed tube	θ_max = 73.9°, θ_min = 3.3°
Graphite monochromator	h = −10→10
Non–profiled ω scans	k = 0→32
2892 measured reflections	l = 0→7
2653 independent reflections	2 standard reflections every 120 min
1784 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.147	w = 1/[σ²(F_o²) + (0.061P)² + 0.4104P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2653 reflections	Δρ_max = 0.23 e Å⁻³
192 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0051 (6)

Crystal data top

C₁₆H₁₃NO₄	V = 1327.6 (4) Å³
M_r = 283.27	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.6001 (17) Å	µ = 0.85 mm⁻¹
b = 27.005 (5) Å	T = 291 K
c = 5.7221 (5) Å	0.08 × 0.06 × 0.04 mm
β = 92.602 (10)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.025
2892 measured reflections	2 standard reflections every 120 min
2653 independent reflections	intensity decay: none
1784 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.05	Δρ_max = 0.23 e Å⁻³
2653 reflections	Δρ_min = −0.24 e Å⁻³
192 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	0.3338 (2)	0.50617 (7)	1.1457 (3)	0.0654 (5)
O2	0.3093 (2)	0.70474 (6)	0.9980 (3)	0.0549 (5)
H2	0.2370	0.6906	1.0585	0.082*
O3	0.1250 (2)	0.65694 (7)	0.3005 (3)	0.0568 (5)
O4	0.1351 (3)	0.48070 (7)	0.7532 (4)	0.0737 (6)
N7	0.2877 (2)	0.68919 (8)	0.5922 (3)	0.0498 (5)
H7	0.2972	0.7182	0.5321	0.060*
C2	0.2445 (4)	0.46150 (12)	1.1374 (6)	0.0810 (10)
H2A	0.1463	0.4671	1.2100	0.097*
H2B	0.3003	0.4360	1.2259	0.097*
C3	0.2138 (5)	0.44427 (12)	0.8942 (7)	0.0878 (11)
H3A	0.3117	0.4361	0.8260	0.105*
H3B	0.1510	0.4144	0.8956	0.105*
C5	0.1581 (3)	0.56216 (9)	0.6119 (4)	0.0536 (6)
H5	0.0937	0.5541	0.4826	0.064*
C6	0.2011 (3)	0.65333 (9)	0.4881 (4)	0.0467 (6)
C8	0.3642 (3)	0.67510 (9)	0.8154 (4)	0.0455 (6)
C9	0.3521 (3)	0.58711 (9)	1.0021 (4)	0.0498 (6)
H9	0.4163	0.5955	1.1313	0.060*
C10	0.2183 (3)	0.60935 (9)	0.6404 (4)	0.0467 (6)
C11	0.3138 (3)	0.62151 (9)	0.8321 (4)	0.0446 (5)
C12	0.1965 (3)	0.52745 (10)	0.7811 (5)	0.0542 (6)
C13	0.2925 (3)	0.53960 (9)	0.9759 (4)	0.0510 (6)
C14	0.5399 (3)	0.68000 (9)	0.8127 (4)	0.0458 (6)
C15	0.6197 (3)	0.66247 (10)	0.6231 (4)	0.0555 (6)
H15	0.5636	0.6499	0.4937	0.067*
C16	0.7790 (3)	0.66338 (11)	0.6228 (5)	0.0645 (7)
H16	0.8301	0.6514	0.4946	0.077*
C17	0.8631 (4)	0.68214 (12)	0.8136 (5)	0.0683 (8)
H17	0.9712	0.6829	0.8143	0.082*
C18	0.7876 (3)	0.69959 (11)	1.0011 (5)	0.0678 (8)
H18	0.8449	0.7121	1.1297	0.081*
C19	0.6268 (3)	0.69889 (10)	1.0022 (4)	0.0561 (7)
H19	0.5767	0.7112	1.1307	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0765 (13)	0.0525 (11)	0.0666 (12)	−0.0020 (9)	−0.0039 (10)	0.0182 (9)
O2	0.0654 (12)	0.0516 (10)	0.0488 (10)	−0.0046 (8)	0.0138 (8)	−0.0083 (8)
O3	0.0575 (11)	0.0718 (12)	0.0406 (9)	−0.0020 (9)	−0.0038 (8)	0.0054 (8)
O4	0.0847 (15)	0.0480 (11)	0.0870 (15)	−0.0136 (10)	−0.0131 (12)	0.0040 (10)
N7	0.0603 (13)	0.0463 (11)	0.0421 (10)	−0.0032 (9)	−0.0049 (9)	0.0071 (9)
C2	0.097 (3)	0.0529 (18)	0.093 (2)	−0.0106 (16)	0.0003 (19)	0.0230 (17)
C3	0.107 (3)	0.0513 (18)	0.104 (3)	−0.0006 (18)	−0.011 (2)	0.0065 (18)
C5	0.0578 (15)	0.0547 (15)	0.0480 (13)	−0.0073 (12)	−0.0020 (11)	−0.0051 (12)
C6	0.0464 (13)	0.0567 (15)	0.0371 (11)	0.0029 (11)	0.0021 (10)	0.0008 (10)
C8	0.0575 (14)	0.0446 (13)	0.0343 (11)	−0.0017 (11)	−0.0001 (10)	−0.0005 (9)
C9	0.0564 (14)	0.0511 (14)	0.0417 (12)	−0.0030 (11)	−0.0005 (10)	0.0034 (11)
C10	0.0512 (13)	0.0500 (14)	0.0388 (11)	−0.0035 (11)	0.0017 (10)	−0.0004 (10)
C11	0.0505 (13)	0.0459 (13)	0.0373 (12)	−0.0014 (10)	0.0022 (10)	0.0010 (10)
C12	0.0608 (16)	0.0454 (14)	0.0565 (15)	−0.0078 (12)	0.0027 (12)	−0.0041 (12)
C13	0.0556 (14)	0.0469 (14)	0.0506 (13)	−0.0001 (11)	0.0042 (11)	0.0074 (11)
C14	0.0567 (14)	0.0436 (13)	0.0370 (11)	−0.0025 (11)	0.0011 (10)	0.0021 (10)
C15	0.0610 (16)	0.0649 (17)	0.0407 (12)	−0.0025 (13)	0.0027 (11)	−0.0039 (12)
C16	0.0606 (16)	0.074 (2)	0.0594 (17)	0.0007 (14)	0.0109 (13)	−0.0030 (15)
C17	0.0570 (16)	0.076 (2)	0.0716 (19)	−0.0002 (14)	0.0011 (14)	0.0022 (16)
C18	0.0635 (18)	0.076 (2)	0.0624 (17)	−0.0039 (15)	−0.0152 (14)	−0.0050 (15)
C19	0.0672 (17)	0.0599 (16)	0.0404 (12)	0.0001 (13)	−0.0040 (11)	−0.0032 (11)

Geometric parameters (Å, º) top

O1—C13	1.362 (3)	C8—C11	1.515 (3)
O1—C2	1.430 (4)	C8—C14	1.518 (3)
O2—C8	1.415 (3)	C9—C11	1.374 (3)
O2—H2	0.8200	C9—C13	1.387 (3)
O3—C6	1.236 (3)	C9—H9	0.9300
O4—C12	1.375 (3)	C10—C11	1.380 (3)
O4—C3	1.424 (4)	C12—C13	1.396 (3)
N7—C6	1.344 (3)	C14—C19	1.386 (3)
N7—C8	1.460 (3)	C14—C15	1.393 (3)
N7—H7	0.8600	C15—C16	1.370 (4)
C2—C3	1.480 (5)	C15—H15	0.9300
C2—H2A	0.9700	C16—C17	1.378 (4)
C2—H2B	0.9700	C16—H16	0.9300
C3—H3A	0.9700	C17—C18	1.363 (4)
C3—H3B	0.9700	C17—H17	0.9300
C5—C12	1.376 (4)	C18—C19	1.384 (4)
C5—C10	1.382 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—H19	0.9300
C6—C10	1.477 (3)

C13—O1—C2	114.4 (2)	C13—C9—H9	120.9
C8—O2—H2	109.5	C11—C10—C5	121.3 (2)
C12—O4—C3	113.5 (2)	C11—C10—C6	108.5 (2)
C6—N7—C8	114.7 (2)	C5—C10—C6	130.2 (2)
C6—N7—H7	122.6	C9—C11—C10	121.1 (2)
C8—N7—H7	122.6	C9—C11—C8	129.1 (2)
O1—C2—C3	111.7 (3)	C10—C11—C8	109.8 (2)
O1—C2—H2A	109.3	O4—C12—C5	117.7 (2)
C3—C2—H2A	109.3	O4—C12—C13	121.2 (2)
O1—C2—H2B	109.3	C5—C12—C13	121.0 (2)
C3—C2—H2B	109.3	O1—C13—C9	116.9 (2)
H2A—C2—H2B	107.9	O1—C13—C12	122.7 (2)
O4—C3—C2	112.1 (3)	C9—C13—C12	120.4 (2)
O4—C3—H3A	109.2	C19—C14—C15	117.8 (2)
C2—C3—H3A	109.2	C19—C14—C8	121.7 (2)
O4—C3—H3B	109.2	C15—C14—C8	120.3 (2)
C2—C3—H3B	109.2	C16—C15—C14	121.5 (3)
H3A—C3—H3B	107.9	C16—C15—H15	119.2
C12—C5—C10	117.9 (2)	C14—C15—H15	119.2
C12—C5—H5	121.0	C15—C16—C17	119.6 (3)
C10—C5—H5	121.0	C15—C16—H16	120.2
O3—C6—N7	126.1 (2)	C17—C16—H16	120.2
O3—C6—C10	127.7 (2)	C18—C17—C16	119.9 (3)
N7—C6—C10	106.23 (19)	C18—C17—H17	120.0
O2—C8—N7	110.3 (2)	C16—C17—H17	120.0
O2—C8—C11	112.82 (19)	C17—C18—C19	120.7 (3)
N7—C8—C11	100.69 (18)	C17—C18—H18	119.7
O2—C8—C14	108.89 (19)	C19—C18—H18	119.7
N7—C8—C14	112.20 (19)	C18—C19—C14	120.4 (3)
C11—C8—C14	111.8 (2)	C18—C19—H19	119.8
C11—C9—C13	118.2 (2)	C14—C19—H19	119.8
C11—C9—H9	120.9

C13—O1—C2—C3	40.4 (4)	C3—O4—C12—C5	162.9 (3)
C12—O4—C3—C2	45.2 (4)	C3—O4—C12—C13	−18.1 (4)
O1—C2—C3—O4	−57.6 (4)	C10—C5—C12—O4	179.4 (2)
C8—N7—C6—O3	179.2 (2)	C10—C5—C12—C13	0.3 (4)
C8—N7—C6—C10	−1.7 (3)	C2—O1—C13—C9	167.3 (3)
C6—N7—C8—O2	−117.5 (2)	C2—O1—C13—C12	−13.5 (4)
C6—N7—C8—C11	1.8 (3)	C11—C9—C13—O1	179.3 (2)
C6—N7—C8—C14	120.9 (2)	C11—C9—C13—C12	0.1 (4)
C12—C5—C10—C11	−0.1 (4)	O4—C12—C13—O1	1.5 (4)
C12—C5—C10—C6	178.4 (3)	C5—C12—C13—O1	−179.5 (2)
O3—C6—C10—C11	179.9 (2)	O4—C12—C13—C9	−179.3 (2)
N7—C6—C10—C11	0.8 (3)	C5—C12—C13—C9	−0.4 (4)
O3—C6—C10—C5	1.3 (4)	O2—C8—C14—C19	16.7 (3)
N7—C6—C10—C5	−177.8 (3)	N7—C8—C14—C19	139.1 (2)
C13—C9—C11—C10	0.2 (4)	C11—C8—C14—C19	−108.6 (3)
C13—C9—C11—C8	−178.9 (2)	O2—C8—C14—C15	−167.4 (2)
C5—C10—C11—C9	−0.2 (4)	N7—C8—C14—C15	−45.1 (3)
C6—C10—C11—C9	−178.9 (2)	C11—C8—C14—C15	67.2 (3)
C5—C10—C11—C8	179.0 (2)	C19—C14—C15—C16	0.5 (4)
C6—C10—C11—C8	0.3 (3)	C8—C14—C15—C16	−175.6 (2)
O2—C8—C11—C9	−64.5 (3)	C14—C15—C16—C17	−0.2 (4)
N7—C8—C11—C9	178.0 (2)	C15—C16—C17—C18	0.1 (5)
C14—C8—C11—C9	58.6 (3)	C16—C17—C18—C19	−0.3 (5)
O2—C8—C11—C10	116.3 (2)	C17—C18—C19—C14	0.5 (5)
N7—C8—C11—C10	−1.2 (3)	C15—C14—C19—C18	−0.6 (4)
C14—C8—C11—C10	−120.5 (2)	C8—C14—C19—C18	175.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.82	1.95	2.725 (3)	158
N7—H7···O2ⁱⁱ	0.86	2.09	2.922 (3)	161
C5—H5···O4ⁱⁱⁱ	0.93	2.52	3.404 (3)	160
C19—H19···O2	0.93	2.40	2.734 (4)	101

Symmetry codes: (i) x, y, z+1; (ii) x, −y+3/2, z−1/2; (iii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃NO₄
M_r	283.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	8.6001 (17), 27.005 (5), 5.7221 (5)
β (°)	92.602 (10)
V (Å³)	1327.6 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.85
Crystal size (mm)	0.08 × 0.06 × 0.04

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2892, 2653, 1784
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.147, 1.05
No. of reflections	2653
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.24

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2000), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.82	1.95	2.725 (3)	158.0
N7—H7···O2ⁱⁱ	0.86	2.09	2.922 (3)	161.4
C5—H5···O4ⁱⁱⁱ	0.93	2.52	3.404 (3)	159.5
C19—H19···O2	0.93	2.40	2.734 (4)	101.3

Symmetry codes: (i) x, y, z+1; (ii) x, −y+3/2, z−1/2; (iii) −x, −y+1, −z+1.

References

Brandenburg, K. (2000). DIAMOND. Release 2.1d. Crystal Impact GbR, Bonn, Germany. Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Version 5.0. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Moorthy, J. N. & Singhal, N. (2005). J. Org. Chem. 70, 1926–1929. Web of Science CrossRef PubMed CAS 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 64| Part 3| March 2008| Page o548

doi:10.1107/S1600536808003012

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