2,10-Dihydr­oxy-13-methyl-13-aza­tetra­cyclo­[9.3.1.02,10.03,8]penta­deca-3(8),4,6-triene-9,15-dione

Suresh, J.; Nithya, U.C.; Kumar, R.S.; Perumal, S.; Lakshman, P.L.N.

doi:10.1107/S1600536809015785

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1216

doi:10.1107/S1600536809015785

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2,10-Dihydroxy-13-methyl-13-azatetracyclo[9.3.1.0^2,10.0^3,8]pentadeca-3(8),4,6-triene-9,15-dione

J. Suresh,^a U. C. Nithya,^a R. Suresh Kumar,^b S. Perumal ^b and P. L. Nilantha Lakshman ^c ^*

^aDepartment of Physics, The Madura College, Madurai 625 011, India, ^bSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^cDepartment of Food Science and Technology, Faculty of Agriculture, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: nilanthalakshman@yahoo.co.uk

(Received 22 April 2009; accepted 28 April 2009; online 7 May 2009)

In the title compound, C₁₅H₁₅NO₄, the n-methylpiperidone ring adopts a chair conformation and both five-membered rings adopt a twist conformation. An intramolecular O—H⋯O hydrogen bond is observed. Inversion-related molecules are linked into R₂²(10) dimers by pairs of O—H⋯O hydrogen bonds. The crystal structure is further stabilized by C—H⋯O hydrogen bonds.

Related literature

For the biological activity of piperidine compounds, see: Watson et al. (2000 ). For ring conformation details, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₅H₁₅NO₄
M_r = 273.28
Triclinic, $[P \overline 1]$
a = 7.5616 (7) Å
b = 8.9033 (8) Å
c = 10.8091 (11) Å
α = 72.764 (11)°
β = 80.486 (12)°
γ = 72.369 (11)°
V = 660.09 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.18 × 0.15 × 0.11 mm

Data collection

Nonius MACH-3 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.982, T_max = 0.989
2890 measured reflections
2316 independent reflections
2025 reflections with I > 2σ(I)
R_int = 0.010
2 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.097
S = 1.11
2316 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	2.11	2.6080 (15)	119
O2—H2⋯O1ⁱ	0.82	1.90	2.7168 (15)	175
C2—H2A⋯O1ⁱ	0.98	2.59	3.3778 (18)	137
C18—H18A⋯O1ⁱⁱ	0.96	2.57	3.432 (2)	149
C5—H5⋯O3ⁱⁱⁱ	0.98	2.46	3.4381 (18)	173
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z; (iii) -x, -y, -z+1.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015785/ci2789sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015785/ci2789Isup2.hkl

checkCIF report

Comment top

The piperidine ring is a distinct structural feature of a variety of alkaloid natural products and drug candidates. Watson et al. (2000) observed that during the past decade there were thousands of piperidine compounds mentioned in clinical and preclinical studies. Piperidinones, though relatively less prominent, have also been regarded as precursors of a host of biologically active compounds and natural alkaloids, prior to their conversion to piperidines. Ninhydrin is a chemical used to detect ammonia or primary and secondary amines.

In the molecule of the title compound, (Fig. 1), the six-membered ring A (N1/C4/C5/C1/C2/C3), and the five membered rings B (C1/C2/C7/C6/C5) and C(C6-C10) are not planar. Rings B and C both adopt twist conformations, as indicated by Cremer & Pople (1975) puckering parameters Q = 0.455 (2) Å and Φ = 160.4 (2)° for ring B, and Q = 0.149 (2) Å and Φ = 21.6 (6)° for ring C. Ring A adopts a chair conformation.

In the crystal structure, the molecules are linked to form dimers by intermolecular O—H···O hydrogen bonds (Table 1), generating a graph set motif of R₂²(10) (Fig.2). In addition, the structure is stabilized by C—H···O and van der Waals interactions.

Related literature top

For the biological activity of piperidine compounds, see: Watson et al. (2000). For ring conformation details, see: Cremer & Pople (1975).

Experimental top

A mixture of 1-methyl-4-piperidinone (0.2 g, 0.002 mol), ninhydrin (0.315 g, 0.002 mol) and sarcosine (0.156 g, 0.002 mol) in methanol (30 ml) was refluxed in a water bath for 10 h. After completion of the reaction as monitored by TLC, the excess solvent was removed under vacuum and the residue was subjected to flash column chromatography using petroleum ether-ethyl acetate mixture (8:2 v/v) as eluent to obtain crystals of title compound in 8% yield along with a other product (yield 13%, m.p. 447–448 K).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity.
	Fig. 2. Partial packing view down the b axis. Hydrogen bonds are shown as dashed lines.

2,10-Dihydroxy-13-methyl-13-azatetracyclo[9.3.1.0^2,10.0^3,8]pentadeca- 3(8),4,6-triene-9,15-dione top

Crystal data top

C₁₅H₁₅NO₄	Z = 2
M_r = 273.28	F(000) = 288
Triclinic, P1	D_x = 1.375 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5616 (7) Å	Cell parameters from 25 reflections
b = 8.9033 (8) Å	θ = 2–25°
c = 10.8091 (11) Å	µ = 0.10 mm⁻¹
α = 72.764 (11)°	T = 293 K
β = 80.486 (12)°	Block, colourless
γ = 72.369 (11)°	0.18 × 0.15 × 0.11 mm
V = 660.09 (11) Å³

Data collection top

Nonius MACH-3 diffractometer	2025 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.010
Graphite monochromator	θ_max = 25.0°, θ_min = 2.5°
ω–2θ scans	h = −1→8
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
T_min = 0.982, T_max = 0.989	l = −12→12
2890 measured reflections	2 standard reflections every 60 min
2316 independent reflections	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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0454P)² + 0.1839P] where P = (F_o² + 2F_c²)/3
2316 reflections	(Δ/σ)_max = 0.001
184 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₅H₁₅NO₄	γ = 72.369 (11)°
M_r = 273.28	V = 660.09 (11) Å³
Triclinic, P1	Z = 2
a = 7.5616 (7) Å	Mo Kα radiation
b = 8.9033 (8) Å	µ = 0.10 mm⁻¹
c = 10.8091 (11) Å	T = 293 K
α = 72.764 (11)°	0.18 × 0.15 × 0.11 mm
β = 80.486 (12)°

Data collection top

Nonius MACH-3 diffractometer	2025 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.010
T_min = 0.982, T_max = 0.989	2 standard reflections every 60 min
2890 measured reflections	intensity decay: none
2316 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.11	Δρ_max = 0.22 e Å⁻³
2316 reflections	Δρ_min = −0.23 e Å⁻³
184 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	0.29809 (15)	0.41843 (13)	0.00498 (10)	0.0446 (3)
O2	−0.04087 (14)	0.29519 (13)	0.08496 (10)	0.0421 (3)
H2	−0.1139	0.3846	0.0581	0.063*
O3	−0.02584 (16)	0.06248 (14)	0.30007 (11)	0.0499 (3)
H3	−0.0724	0.0852	0.2313	0.075*
N1	0.29935 (17)	0.38335 (15)	0.28995 (12)	0.0388 (3)
O4	−0.19177 (16)	0.40313 (16)	0.45054 (11)	0.0538 (3)
C8	0.2679 (2)	0.30815 (17)	0.09849 (13)	0.0353 (3)
C4	0.2670 (2)	0.26334 (19)	0.41090 (14)	0.0403 (3)
H4A	0.2445	0.3121	0.4832	0.048*
H4B	0.3768	0.1712	0.4252	0.048*
C10	0.3067 (2)	0.04870 (17)	0.24458 (14)	0.0372 (3)
C7	0.07412 (19)	0.30768 (16)	0.17048 (13)	0.0322 (3)
C5	0.0984 (2)	0.20371 (18)	0.40485 (13)	0.0375 (3)
H5	0.0730	0.1229	0.4847	0.045*
C6	0.1144 (2)	0.14491 (16)	0.28236 (13)	0.0348 (3)
C9	0.3957 (2)	0.14516 (17)	0.14346 (14)	0.0372 (3)
C1	−0.0622 (2)	0.35556 (19)	0.37706 (14)	0.0383 (3)
C3	0.1375 (2)	0.52059 (18)	0.25385 (15)	0.0406 (3)
H3A	0.1661	0.5959	0.1728	0.049*
H3B	0.0969	0.5788	0.3209	0.049*
C2	−0.0144 (2)	0.44610 (17)	0.23864 (13)	0.0362 (3)
H2A	−0.1220	0.5275	0.1970	0.043*
C14	0.5784 (2)	0.0851 (2)	0.09741 (16)	0.0486 (4)
H14	0.6375	0.1503	0.0301	0.058*
C11	0.3986 (2)	−0.11196 (19)	0.30063 (17)	0.0496 (4)
H11	0.3394	−0.1777	0.3674	0.059*
C12	0.5804 (3)	−0.1720 (2)	0.25488 (18)	0.0565 (5)
H12	0.6442	−0.2794	0.2917	0.068*
C13	0.6699 (2)	−0.0751 (2)	0.15496 (19)	0.0572 (5)
H13	0.7927	−0.1183	0.1263	0.069*
C18	0.4702 (3)	0.4293 (3)	0.2839 (2)	0.0624 (5)
H18A	0.4881	0.5036	0.2010	0.094*
H18B	0.5737	0.3334	0.2949	0.094*
H18C	0.4615	0.4811	0.3517	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0438 (6)	0.0456 (6)	0.0332 (5)	−0.0098 (5)	0.0005 (4)	0.0021 (5)
O2	0.0419 (6)	0.0433 (6)	0.0416 (6)	−0.0060 (5)	−0.0146 (5)	−0.0116 (5)
O3	0.0522 (7)	0.0488 (6)	0.0518 (7)	−0.0269 (5)	−0.0081 (5)	−0.0022 (5)
N1	0.0360 (7)	0.0438 (7)	0.0393 (7)	−0.0155 (5)	0.0001 (5)	−0.0116 (5)
O4	0.0413 (6)	0.0706 (8)	0.0475 (7)	−0.0118 (6)	0.0104 (5)	−0.0234 (6)
C8	0.0365 (8)	0.0379 (7)	0.0285 (7)	−0.0084 (6)	−0.0037 (6)	−0.0053 (6)
C4	0.0413 (8)	0.0455 (8)	0.0329 (7)	−0.0085 (6)	−0.0075 (6)	−0.0095 (6)
C10	0.0422 (8)	0.0343 (7)	0.0341 (7)	−0.0068 (6)	−0.0073 (6)	−0.0090 (6)
C7	0.0320 (7)	0.0335 (7)	0.0289 (7)	−0.0067 (6)	−0.0057 (5)	−0.0053 (6)
C5	0.0396 (8)	0.0413 (8)	0.0268 (7)	−0.0130 (6)	0.0003 (6)	−0.0013 (6)
C6	0.0369 (8)	0.0322 (7)	0.0338 (7)	−0.0120 (6)	−0.0039 (6)	−0.0030 (6)
C9	0.0378 (8)	0.0387 (8)	0.0326 (7)	−0.0050 (6)	−0.0052 (6)	−0.0101 (6)
C1	0.0350 (8)	0.0468 (8)	0.0360 (8)	−0.0141 (6)	0.0002 (6)	−0.0135 (6)
C3	0.0491 (9)	0.0361 (8)	0.0370 (8)	−0.0128 (7)	−0.0008 (6)	−0.0100 (6)
C2	0.0349 (7)	0.0354 (7)	0.0339 (7)	−0.0028 (6)	−0.0053 (6)	−0.0080 (6)
C14	0.0396 (8)	0.0557 (10)	0.0453 (9)	−0.0037 (7)	−0.0015 (7)	−0.0160 (8)
C11	0.0600 (10)	0.0342 (8)	0.0482 (9)	−0.0044 (7)	−0.0111 (8)	−0.0064 (7)
C12	0.0617 (11)	0.0404 (9)	0.0592 (11)	0.0085 (8)	−0.0191 (9)	−0.0161 (8)
C13	0.0442 (9)	0.0592 (11)	0.0625 (11)	0.0096 (8)	−0.0102 (8)	−0.0286 (9)
C18	0.0456 (10)	0.0723 (12)	0.0787 (13)	−0.0281 (9)	0.0013 (9)	−0.0244 (10)

Geometric parameters (Å, º) top

O1—C8	1.2285 (17)	C5—C1	1.509 (2)
O2—C7	1.4171 (16)	C5—C6	1.537 (2)
O2—H2	0.82	C5—H5	0.98
O3—C6	1.4219 (17)	C9—C14	1.387 (2)
O3—H3	0.82	C1—C2	1.517 (2)
N1—C3	1.453 (2)	C3—C2	1.541 (2)
N1—C18	1.455 (2)	C3—H3A	0.97
N1—C4	1.4613 (19)	C3—H3B	0.97
O4—C1	1.2088 (18)	C2—H2A	0.98
C8—C9	1.471 (2)	C14—C13	1.385 (3)
C8—C7	1.5419 (19)	C14—H14	0.93
C4—C5	1.539 (2)	C11—C12	1.381 (3)
C4—H4A	0.97	C11—H11	0.93
C4—H4B	0.97	C12—C13	1.388 (3)
C10—C11	1.386 (2)	C12—H12	0.93
C10—C9	1.391 (2)	C13—H13	0.93
C10—C6	1.507 (2)	C18—H18A	0.96
C7—C2	1.5443 (19)	C18—H18B	0.96
C7—C6	1.5720 (18)	C18—H18C	0.96

C7—O2—H2	109.5	C14—C9—C8	128.62 (14)
C6—O3—H3	109.5	C10—C9—C8	109.95 (13)
C3—N1—C18	114.32 (13)	O4—C1—C5	128.54 (14)
C3—N1—C4	113.97 (12)	O4—C1—C2	126.94 (14)
C18—N1—C4	112.86 (13)	C5—C1—C2	104.23 (11)
O1—C8—C9	126.53 (13)	N1—C3—C2	105.67 (11)
O1—C8—C7	124.00 (12)	N1—C3—H3A	110.6
C9—C8—C7	108.44 (12)	C2—C3—H3A	110.6
N1—C4—C5	110.50 (11)	N1—C3—H3B	110.6
N1—C4—H4A	109.6	C2—C3—H3B	110.6
C5—C4—H4A	109.6	H3A—C3—H3B	108.7
N1—C4—H4B	109.6	C1—C2—C3	103.05 (11)
C5—C4—H4B	109.6	C1—C2—C7	103.33 (11)
H4A—C4—H4B	108.1	C3—C2—C7	109.41 (11)
C11—C10—C9	120.35 (15)	C1—C2—H2A	113.4
C11—C10—C6	128.39 (14)	C3—C2—H2A	113.4
C9—C10—C6	111.20 (12)	C7—C2—H2A	113.4
O2—C7—C8	108.50 (11)	C13—C14—C9	117.82 (16)
O2—C7—C2	114.39 (11)	C13—C14—H14	121.1
C8—C7—C2	115.40 (12)	C9—C14—H14	121.1
O2—C7—C6	108.69 (11)	C12—C11—C10	118.30 (16)
C8—C7—C6	103.21 (11)	C12—C11—H11	120.8
C2—C7—C6	105.84 (11)	C10—C11—H11	120.8
C1—C5—C6	100.91 (11)	C11—C12—C13	121.32 (15)
C1—C5—C4	105.49 (12)	C11—C12—H12	119.3
C6—C5—C4	112.08 (11)	C13—C12—H12	119.3
C1—C5—H5	112.5	C14—C13—C12	120.77 (16)
C6—C5—H5	112.5	C14—C13—H13	119.6
C4—C5—H5	112.5	C12—C13—H13	119.6
O3—C6—C10	114.30 (12)	N1—C18—H18A	109.5
O3—C6—C5	106.98 (11)	N1—C18—H18B	109.5
C10—C6—C5	114.94 (12)	H18A—C18—H18B	109.5
O3—C6—C7	111.58 (11)	N1—C18—H18C	109.5
C10—C6—C7	104.97 (11)	H18A—C18—H18C	109.5
C5—C6—C7	103.62 (11)	H18B—C18—H18C	109.5
C14—C9—C10	121.43 (14)

C3—N1—C4—C5	54.45 (16)	C6—C10—C9—C14	176.26 (14)
C18—N1—C4—C5	−172.98 (13)	C11—C10—C9—C8	178.38 (14)
O1—C8—C7—O2	66.57 (17)	C6—C10—C9—C8	−4.31 (17)
C9—C8—C7—O2	−102.49 (12)	O1—C8—C9—C14	4.9 (3)
O1—C8—C7—C2	−63.28 (18)	C7—C8—C9—C14	173.60 (15)
C9—C8—C7—C2	127.66 (12)	O1—C8—C9—C10	−174.49 (14)
O1—C8—C7—C6	−178.24 (13)	C7—C8—C9—C10	−5.78 (16)
C9—C8—C7—C6	12.70 (14)	C6—C5—C1—O4	138.05 (16)
N1—C4—C5—C1	−56.97 (15)	C4—C5—C1—O4	−105.16 (17)
N1—C4—C5—C6	51.96 (16)	C6—C5—C1—C2	−47.81 (13)
C11—C10—C6—O3	−48.1 (2)	C4—C5—C1—C2	68.98 (13)
C9—C10—C6—O3	134.84 (13)	C18—N1—C3—C2	168.31 (13)
C11—C10—C6—C5	76.15 (19)	C4—N1—C3—C2	−59.82 (15)
C9—C10—C6—C5	−100.88 (14)	O4—C1—C2—C3	98.33 (17)
C11—C10—C6—C7	−170.70 (15)	C5—C1—C2—C3	−75.95 (13)
C9—C10—C6—C7	12.27 (15)	O4—C1—C2—C7	−147.76 (15)
C1—C5—C6—O3	−80.03 (13)	C5—C1—C2—C7	37.97 (14)
C4—C5—C6—O3	168.14 (11)	N1—C3—C2—C1	69.03 (14)
C1—C5—C6—C10	151.91 (12)	N1—C3—C2—C7	−40.39 (14)
C4—C5—C6—C10	40.09 (16)	O2—C7—C2—C1	106.41 (13)
C1—C5—C6—C7	37.97 (13)	C8—C7—C2—C1	−126.65 (12)
C4—C5—C6—C7	−73.85 (14)	C6—C7—C2—C1	−13.22 (14)
O2—C7—C6—O3	−23.90 (15)	O2—C7—C2—C3	−144.35 (12)
C8—C7—C6—O3	−138.96 (12)	C8—C7—C2—C3	−17.42 (15)
C2—C7—C6—O3	99.41 (13)	C6—C7—C2—C3	96.02 (13)
O2—C7—C6—C10	100.42 (12)	C10—C9—C14—C13	0.3 (2)
C8—C7—C6—C10	−14.64 (14)	C8—C9—C14—C13	−178.97 (15)
C2—C7—C6—C10	−136.28 (11)	C9—C10—C11—C12	1.0 (2)
O2—C7—C6—C5	−138.66 (11)	C6—C10—C11—C12	−175.81 (15)
C8—C7—C6—C5	106.28 (12)	C10—C11—C12—C13	−0.3 (3)
C2—C7—C6—C5	−15.36 (14)	C9—C14—C13—C12	0.4 (3)
C11—C10—C9—C14	−1.1 (2)	C11—C12—C13—C14	−0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	2.11	2.6080 (15)	119
O2—H2···O1ⁱ	0.82	1.90	2.7168 (15)	175
C2—H2A···O1ⁱ	0.98	2.59	3.3778 (18)	137
C18—H18A···O1ⁱⁱ	0.96	2.57	3.432 (2)	149
C5—H5···O3ⁱⁱⁱ	0.98	2.46	3.4381 (18)	173

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO₄
M_r	273.28
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.5616 (7), 8.9033 (8), 10.8091 (11)
α, β, γ (°)	72.764 (11), 80.486 (12), 72.369 (11)
V (Å³)	660.09 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.18 × 0.15 × 0.11

Data collection
Diffractometer	Nonius MACH-3 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.982, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	2890, 2316, 2025
R_int	0.010
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.097, 1.11
No. of reflections	2316
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.23

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	2.11	2.6080 (15)	119
O2—H2···O1ⁱ	0.82	1.90	2.7168 (15)	175
C2—H2A···O1ⁱ	0.98	2.59	3.3778 (18)	137
C18—H18A···O1ⁱⁱ	0.96	2.57	3.432 (2)	149
C5—H5···O3ⁱⁱⁱ	0.98	2.46	3.4381 (18)	173

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

Acknowledgements

JS and UCN thank the Management of the Madura College, Madurai, for their constant support.

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watson, P. S., Jiang, B. & Scott, B. (2000). Org. Lett. 2, 3679–3681. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 65| Part 6| June 2009| Page o1216

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,10-Dihydr­­oxy-13-methyl-13-aza­tetra­cyclo­[9.3.1.02,10.03,8]penta­deca-3(8),4,6-triene-9,15-dione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,10-Dihydroxy-13-methyl-13-azatetracyclo[9.3.1.0^2,10.0^3,8]pentadeca-3(8),4,6-triene-9,15-dione