10-Hydr­oxy-2-aza­penta­cyclo­[10.8.0.02,10.04,9.015,20]icosa-1(12),4(9),5,7,13,15(20),16,18-octa­ene-3,11-dione

Hashemian, S.; Notash, B.

doi:10.1107/S1600536811005356

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o680

doi:10.1107/S1600536811005356

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10-Hydroxy-2-azapentacyclo[10.8.0.0^2,10.0^4,9.0^15,20]icosa-1(12),4(9),5,7,13,15(20),16,18-octaene-3,11-dione

Saeedeh Hashemian ^a ^* and Behrouz Notash ^b

^aDepartment of Chemistry, Islamic Azad University, Yazd Branch, Yazd, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: sa_hashemian@yahoo.com

(Received 8 February 2011; accepted 13 February 2011; online 23 February 2011)

In the title compound, C₁₉H₁₁NO₃, the isoindolinone ring system is approximately planar with a maximum atomic deviation of 0.071 (1) Å and the five-membered ring of the dihydrobenzo[g]indol-3-one unit assumes an envelope conformation. The naphthalene ring system makes a dihedral angle of 39.47 (4)° with the mean plane of the isoindolinone system. Intermolecular O—H⋯O and C—H⋯O hydrogen bonding helps to stabilize the crystal structure.

Related literature

For applications of naphthylamines, see Valenti et al. (2006 ); Black et al. (1994 ).

Experimental

Crystal data

C₁₉H₁₁NO₃
M_r = 301.29
Triclinic, $[P \overline 1]$
a = 7.3250 (11) Å
b = 9.7916 (16) Å
c = 10.4532 (17) Å
α = 70.401 (13)°
β = 82.503 (13)°
γ = 75.862 (12)°
V = 683.94 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.40 × 0.30 × 0.29 mm

Data collection

Stoe IPDS II diffractometer
7737 measured reflections
3627 independent reflections
3161 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.136
S = 1.13
3627 reflections
212 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.96 (2)	1.85 (2)	2.7978 (15)	172.2 (17)
C6—H6⋯O3ⁱⁱ	0.93	2.52	3.1609 (18)	126
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z.

Data collection: X-RED32 (Stoe & Cie, 2005 ); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005356/xu5159sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005356/xu5159Isup2.hkl

checkCIF report

Comment top

Naphthylamine is an aromatic amine which can be obtained from nitronaphthalene. Naphthylamines are used in the manufacture of dyes, condensation colors, and rubber and in the synthesis of a large number of chemical (Black et al. 1994; Valenti et al. 2006). Ninhydrin (2,2-dihydroxyindane-1,3-dione) is a chemical used to detect ammonia or primary and secondary amines. The carbon atom of a carbonyl bears a partial positive charge enhanced by neighboring electron withdrawing groups like carbonyl itself. So the central carbon of a 1,2,3-tricarbonyl compound is much more electrophilic than one in a simple ketone. Thus indane-1,2,3-trione reacts readily with nucleophiles, including water. Whereas for most carbonyl compounds, a carbonyl form is more stable than a product of water addition (hydrate), ninhydrin forms a stable hydrate of the central carbon because of the destabilizing effect of the adjacent carbonyl groups.

We report here the crystal structure of 7-hydroxy-7-aH-benzo[g] isoindolino[1,2-α]indole-7,10-dione. The title compound was prepared by the reaction of α-naphthylamine and ninhydrine in molar ratio of 1: 1 in acetone. The structure of title complex is shown in Fig. 1. There are intermolecular hydrogen bondings between O—H···O and C—H···O which play important role in the stabilization of crystalline network (Table 1 & Fig. 2).

Related literature top

For applications of naphthylamines, see Valenti et al. (2006); Black et al. (1994).

Experimental top

The title compound was prepared by the reaction of α- naphthylamine and ninhydrine in molar ratio of 1: 1 in acetone. The mixture was stirred for about 2 h at room temperature. The resulting solution was kept in air. After slow evaporation, single crystals of the title compound suitable for an X-ray diffraction study formed at the bottom of the vessel after 2 weeks (m.p. 138 °C).

Computing details top

Data collection: X-RED32 (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level.
	Fig. 2. The packing diagram of the title compound. The intermolecular O—H···O and C—H···O hydrogen bonds are shown as blue dashed lines.

10-Hydroxy-2-azapentacyclo[10.8.0.0^2,10.0^4,9.0^15,20]icosa- 1(12),4(9),5,7,13,15 (20),16,18-octaene-3,11-dione top

Crystal data top

C₁₉H₁₁NO₃	Z = 2
M_r = 301.29	F(000) = 312
Triclinic, P1	D_x = 1.463 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3250 (11) Å	Cell parameters from 1011 reflections
b = 9.7916 (16) Å	θ = 2.3–25.0°
c = 10.4532 (17) Å	µ = 0.10 mm⁻¹
α = 70.401 (13)°	T = 298 K
β = 82.503 (13)°	Block, colorless
γ = 75.862 (12)°	0.40 × 0.30 × 0.29 mm
V = 683.94 (19) Å³

Data collection top

Stoe IPDS II diffractometer	3161 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.040
Graphite monochromator	θ_max = 29.3°, θ_min = 2.3°
rotation method scans	h = −10→10
7737 measured reflections	k = −13→13
3627 independent reflections	l = −14→14

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ²(F_o²) + (0.072P)² + 0.1037P] where P = (F_o² + 2F_c²)/3
3627 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₉H₁₁NO₃	γ = 75.862 (12)°
M_r = 301.29	V = 683.94 (19) Å³
Triclinic, P1	Z = 2
a = 7.3250 (11) Å	Mo Kα radiation
b = 9.7916 (16) Å	µ = 0.10 mm⁻¹
c = 10.4532 (17) Å	T = 298 K
α = 70.401 (13)°	0.40 × 0.30 × 0.29 mm
β = 82.503 (13)°

Data collection top

Stoe IPDS II diffractometer	3161 reflections with I > 2σ(I)
7737 measured reflections	R_int = 0.040
3627 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.29 e Å⁻³
3627 reflections	Δρ_min = −0.22 e Å⁻³
212 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
C1	0.60706 (15)	0.62937 (12)	0.49240 (11)	0.0298 (2)
C2	0.69780 (16)	0.61664 (13)	0.36032 (12)	0.0324 (2)
C3	0.87442 (18)	0.53663 (16)	0.33404 (14)	0.0410 (3)
H3	0.9488	0.4711	0.4042	0.049*
C4	0.9358 (2)	0.55825 (19)	0.19890 (16)	0.0494 (3)
H4	1.0540	0.5065	0.1779	0.059*
C5	0.8237 (2)	0.65604 (19)	0.09393 (15)	0.0502 (3)
H5	0.8694	0.6697	0.0042	0.060*
C6	0.6452 (2)	0.73333 (16)	0.12066 (13)	0.0425 (3)
H6	0.5690	0.7968	0.0507	0.051*
C7	0.58481 (16)	0.71222 (13)	0.25611 (12)	0.0332 (2)
C8	0.40104 (16)	0.77784 (12)	0.31604 (11)	0.0318 (2)
C9	0.33814 (17)	0.94765 (13)	0.28511 (13)	0.0374 (3)
C10	0.29102 (17)	0.97079 (13)	0.41761 (13)	0.0358 (3)
C11	0.19816 (19)	1.10289 (14)	0.44465 (16)	0.0441 (3)
H11	0.1640	1.1909	0.3742	0.053*
C12	0.15988 (19)	1.09807 (16)	0.57670 (17)	0.0469 (3)
H12	0.0981	1.1843	0.5963	0.056*
C13	0.21185 (17)	0.96457 (16)	0.68549 (15)	0.0413 (3)
C14	0.1701 (2)	0.9614 (2)	0.82289 (17)	0.0541 (4)
H14	0.1102	1.0485	0.8415	0.065*
C15	0.2156 (2)	0.8347 (2)	0.92698 (17)	0.0596 (4)
H15	0.1890	0.8359	1.0161	0.071*
C16	0.3028 (2)	0.7010 (2)	0.90168 (15)	0.0545 (4)
H16	0.3306	0.6140	0.9742	0.065*
C17	0.34726 (19)	0.69747 (16)	0.77121 (13)	0.0422 (3)
H17	0.4051	0.6082	0.7558	0.051*
C18	0.30558 (16)	0.82910 (14)	0.65996 (12)	0.0344 (2)
C19	0.34334 (15)	0.83897 (12)	0.52100 (12)	0.0310 (2)
O1	0.67384 (13)	0.57343 (10)	0.60386 (9)	0.0374 (2)
O2	0.24447 (12)	0.73626 (10)	0.28658 (9)	0.0376 (2)
H2	0.268 (3)	0.630 (2)	0.317 (2)	0.066 (6)*
O3	0.32112 (19)	1.03639 (12)	0.17284 (11)	0.0592 (3)
N1	0.43075 (13)	0.72309 (10)	0.46469 (9)	0.0303 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0310 (5)	0.0265 (5)	0.0314 (5)	−0.0044 (4)	−0.0037 (4)	−0.0091 (4)
C2	0.0318 (5)	0.0332 (5)	0.0334 (5)	−0.0057 (4)	−0.0021 (4)	−0.0128 (4)
C3	0.0329 (6)	0.0468 (7)	0.0462 (7)	−0.0022 (5)	−0.0040 (5)	−0.0221 (6)
C4	0.0366 (6)	0.0628 (9)	0.0545 (8)	−0.0073 (6)	0.0071 (6)	−0.0317 (7)
C5	0.0490 (8)	0.0656 (9)	0.0402 (7)	−0.0176 (7)	0.0120 (6)	−0.0237 (7)
C6	0.0460 (7)	0.0487 (7)	0.0309 (6)	−0.0114 (5)	0.0016 (5)	−0.0106 (5)
C7	0.0339 (5)	0.0342 (5)	0.0308 (5)	−0.0075 (4)	−0.0004 (4)	−0.0096 (4)
C8	0.0328 (5)	0.0321 (5)	0.0268 (5)	−0.0041 (4)	−0.0038 (4)	−0.0057 (4)
C9	0.0367 (6)	0.0319 (5)	0.0370 (6)	−0.0045 (4)	−0.0026 (4)	−0.0040 (4)
C10	0.0323 (5)	0.0302 (5)	0.0430 (6)	−0.0053 (4)	−0.0014 (4)	−0.0104 (5)
C11	0.0384 (6)	0.0293 (6)	0.0628 (8)	−0.0041 (5)	−0.0020 (6)	−0.0146 (5)
C12	0.0378 (6)	0.0398 (7)	0.0697 (9)	−0.0068 (5)	0.0044 (6)	−0.0297 (7)
C13	0.0310 (5)	0.0490 (7)	0.0540 (7)	−0.0105 (5)	0.0038 (5)	−0.0301 (6)
C14	0.0438 (7)	0.0725 (10)	0.0611 (9)	−0.0126 (7)	0.0084 (6)	−0.0447 (9)
C15	0.0510 (8)	0.0929 (13)	0.0467 (8)	−0.0148 (8)	0.0065 (6)	−0.0413 (9)
C16	0.0540 (8)	0.0735 (10)	0.0354 (7)	−0.0126 (7)	0.0017 (6)	−0.0188 (7)
C17	0.0428 (7)	0.0495 (7)	0.0346 (6)	−0.0087 (5)	0.0009 (5)	−0.0158 (5)
C18	0.0290 (5)	0.0408 (6)	0.0379 (6)	−0.0088 (4)	0.0016 (4)	−0.0184 (5)
C19	0.0278 (5)	0.0304 (5)	0.0353 (5)	−0.0060 (4)	0.0001 (4)	−0.0119 (4)
O1	0.0403 (5)	0.0356 (4)	0.0330 (4)	−0.0006 (3)	−0.0097 (3)	−0.0091 (3)
O2	0.0338 (4)	0.0389 (5)	0.0380 (4)	−0.0049 (3)	−0.0085 (3)	−0.0089 (4)
O3	0.0753 (8)	0.0408 (6)	0.0421 (5)	−0.0017 (5)	−0.0040 (5)	0.0047 (4)
N1	0.0325 (5)	0.0292 (4)	0.0265 (4)	−0.0019 (3)	−0.0028 (3)	−0.0080 (3)

Geometric parameters (Å, º) top

C1—O1	1.2192 (14)	C10—C19	1.3826 (16)
C1—N1	1.3908 (14)	C10—C11	1.4075 (17)
C1—C2	1.4829 (16)	C11—C12	1.359 (2)
C2—C3	1.3855 (16)	C11—H11	0.9300
C2—C7	1.3858 (16)	C12—C13	1.421 (2)
C3—C4	1.387 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.420 (2)
C4—C5	1.393 (2)	C13—C18	1.4307 (17)
C4—H4	0.9300	C14—C15	1.349 (3)
C5—C6	1.387 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.404 (3)
C6—C7	1.3885 (17)	C15—H15	0.9300
C6—H6	0.9300	C16—C17	1.3704 (18)
C7—C8	1.4983 (16)	C16—H16	0.9300
C8—O2	1.4071 (14)	C17—C18	1.4148 (19)
C8—N1	1.4905 (14)	C17—H17	0.9300
C8—C9	1.5445 (16)	C18—C19	1.4177 (16)
C9—O3	1.2037 (16)	C19—N1	1.4278 (14)
C9—C10	1.4616 (18)	O2—H2	0.96 (2)

O1—C1—N1	125.83 (10)	C11—C10—C9	127.75 (12)
O1—C1—C2	127.52 (10)	C12—C11—C10	118.08 (13)
N1—C1—C2	106.62 (9)	C12—C11—H11	121.0
C3—C2—C7	121.55 (11)	C10—C11—H11	121.0
C3—C2—C1	128.81 (11)	C11—C12—C13	121.64 (12)
C7—C2—C1	109.36 (10)	C11—C12—H12	119.2
C2—C3—C4	117.33 (12)	C13—C12—H12	119.2
C2—C3—H3	121.3	C14—C13—C12	120.91 (13)
C4—C3—H3	121.3	C14—C13—C18	118.03 (14)
C3—C4—C5	121.23 (13)	C12—C13—C18	121.06 (12)
C3—C4—H4	119.4	C15—C14—C13	121.45 (14)
C5—C4—H4	119.4	C15—C14—H14	119.3
C6—C5—C4	121.25 (12)	C13—C14—H14	119.3
C6—C5—H5	119.4	C14—C15—C16	120.45 (14)
C4—C5—H5	119.4	C14—C15—H15	119.8
C5—C6—C7	117.34 (13)	C16—C15—H15	119.8
C5—C6—H6	121.3	C17—C16—C15	120.69 (16)
C7—C6—H6	121.3	C17—C16—H16	119.7
C2—C7—C6	121.28 (11)	C15—C16—H16	119.7
C2—C7—C8	109.15 (10)	C16—C17—C18	120.21 (14)
C6—C7—C8	129.57 (11)	C16—C17—H17	119.9
O2—C8—N1	111.82 (9)	C18—C17—H17	119.9
O2—C8—C7	113.83 (9)	C17—C18—C19	125.32 (11)
N1—C8—C7	103.29 (9)	C17—C18—C13	119.13 (12)
O2—C8—C9	104.10 (9)	C19—C18—C13	115.52 (12)
N1—C8—C9	103.13 (9)	C10—C19—C18	121.92 (11)
C7—C8—C9	120.25 (10)	C10—C19—N1	109.84 (10)
O3—C9—C10	129.58 (12)	C18—C19—N1	128.21 (10)
O3—C9—C8	124.77 (12)	C8—O2—H2	107.6 (12)
C10—C9—C8	105.45 (9)	C1—N1—C19	126.89 (9)
C19—C10—C11	121.77 (12)	C1—N1—C8	111.06 (9)
C19—C10—C9	110.43 (10)	C19—N1—C8	108.74 (9)

O1—C1—C2—C3	1.8 (2)	C11—C12—C13—C18	−0.5 (2)
N1—C1—C2—C3	179.64 (12)	C12—C13—C14—C15	178.73 (14)
O1—C1—C2—C7	−172.16 (12)	C18—C13—C14—C15	−0.5 (2)
N1—C1—C2—C7	5.70 (13)	C13—C14—C15—C16	−1.3 (2)
C7—C2—C3—C4	1.3 (2)	C14—C15—C16—C17	1.6 (3)
C1—C2—C3—C4	−171.95 (12)	C15—C16—C17—C18	0.0 (2)
C2—C3—C4—C5	−0.3 (2)	C16—C17—C18—C19	−179.45 (13)
C3—C4—C5—C6	−1.2 (2)	C16—C17—C18—C13	−1.7 (2)
C4—C5—C6—C7	1.6 (2)	C14—C13—C18—C17	2.00 (18)
C3—C2—C7—C6	−0.90 (19)	C12—C13—C18—C17	−177.24 (12)
C1—C2—C7—C6	173.56 (11)	C14—C13—C18—C19	179.92 (11)
C3—C2—C7—C8	177.95 (11)	C12—C13—C18—C19	0.68 (17)
C1—C2—C7—C8	−7.60 (13)	C11—C10—C19—C18	0.37 (18)
C5—C6—C7—C2	−0.6 (2)	C9—C10—C19—C18	−177.05 (10)
C5—C6—C7—C8	−179.17 (13)	C11—C10—C19—N1	178.75 (11)
C2—C7—C8—O2	−115.06 (11)	C9—C10—C19—N1	1.33 (14)
C6—C7—C8—O2	63.66 (17)	C17—C18—C19—C10	177.17 (12)
C2—C7—C8—N1	6.39 (12)	C13—C18—C19—C10	−0.61 (17)
C6—C7—C8—N1	−174.89 (13)	C17—C18—C19—N1	−0.9 (2)
C2—C7—C8—C9	120.48 (11)	C13—C18—C19—N1	−178.66 (10)
C6—C7—C8—C9	−60.81 (18)	O1—C1—N1—C19	40.41 (18)
O2—C8—C9—O3	−72.49 (16)	C2—C1—N1—C19	−137.50 (11)
N1—C8—C9—O3	170.63 (13)	O1—C1—N1—C8	176.42 (11)
C7—C8—C9—O3	56.47 (18)	C2—C1—N1—C8	−1.48 (12)
O2—C8—C9—C10	102.75 (10)	C10—C19—N1—C1	125.80 (12)
N1—C8—C9—C10	−14.13 (12)	C18—C19—N1—C1	−55.95 (17)
C7—C8—C9—C10	−128.29 (11)	C10—C19—N1—C8	−11.01 (13)
O3—C9—C10—C19	−176.69 (14)	C18—C19—N1—C8	167.23 (11)
C8—C9—C10—C19	8.38 (13)	O2—C8—N1—C1	119.96 (10)
O3—C9—C10—C11	6.1 (2)	C7—C8—N1—C1	−2.84 (12)
C8—C9—C10—C11	−168.84 (12)	C9—C8—N1—C1	−128.76 (10)
C19—C10—C11—C12	−0.18 (19)	O2—C8—N1—C19	−95.95 (11)
C9—C10—C11—C12	176.77 (12)	C7—C8—N1—C19	141.25 (9)
C10—C11—C12—C13	0.3 (2)	C9—C8—N1—C19	15.33 (11)
C11—C12—C13—C14	−179.76 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.96 (2)	1.85 (2)	2.7978 (15)	172.2 (17)
C6—H6···O3ⁱⁱ	0.93	2.52	3.1609 (18)	126

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₁NO₃
M_r	301.29
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.3250 (11), 9.7916 (16), 10.4532 (17)
α, β, γ (°)	70.401 (13), 82.503 (13), 75.862 (12)
V (Å³)	683.94 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.30 × 0.29

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7737, 3627, 3161
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.136, 1.13
No. of reflections	3627
No. of parameters	212
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.22

Computer programs: X-RED32 (Stoe & Cie, 2005), X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.96 (2)	1.85 (2)	2.7978 (15)	172.2 (17)
C6—H6···O3ⁱⁱ	0.93	2.52	3.1609 (18)	126

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

Acknowledgements

We are grateful to the Islamic Azad University, Yazd Branch, for financial support.

References

Black, D. S. C., Bowyer, M. C., Condie, G. C., Craig, D. C. & Kumar, N. (1994). Tetrahedron, 50, 10983–10994. CSD CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2005). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar
Valenti, L. E., De Pauli, C. P. & Giacomelli, C. E. (2006). J. Inorg. Biochem. 100, 192–200. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 67| Part 3| March 2011| Page o680

doi:10.1107/S1600536811005356

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

10-Hydr­­oxy-2-aza­penta­cyclo­[10.8.0.02,10.04,9.015,20]icosa-1(12),4(9),5,7,13,15(20),16,18-octa­ene-3,11-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

10-Hydroxy-2-azapentacyclo[10.8.0.0^2,10.0^4,9.0^15,20]icosa-1(12),4(9),5,7,13,15(20),16,18-octaene-3,11-dione